#------------------------------------------------------------------------------ #$Date: 2024-06-20 01:22:26 +0300 (Thu, 20 Jun 2024) $ #$Revision: 292468 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/19/1571945.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_1571945 loop_ _publ_author_name 'Arnold, Robert' 'Saska, Jan' 'Mesquita-Ribeiro, Raquel' 'Dajas-Bailador, Federico' 'Lewis, William' 'Taylor, Laurence John' 'Argent, Stephen' 'Shaoh, Huiling' 'Houk, K. N.' 'Denton, Ross Matthew' _publ_section_title ; Total Synthesis, Biological Evaluation and Biosynthetic Re-Evaluation of Illicium-Derived Neolignans ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D4SC03232B _journal_year 2024 _chemical_formula_moiety 'C19 H19 Br O3' _chemical_formula_sum 'C19 H19 Br O3' _chemical_formula_weight 375.25 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary iterative _atom_sites_solution_secondary difmap _audit_creation_date 2018-02-10 _audit_creation_method ; Olex2 1.2 (compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381) ; _audit_update_record ; 2024-01-23 deposited with the CCDC. 2024-06-13 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 100.156(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.0694(3) _cell_length_b 10.5320(3) _cell_length_c 17.2799(6) _cell_measurement_reflns_used 4257 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 74.2860 _cell_measurement_theta_min 4.1770 _cell_volume 1624.70(9) _computing_cell_refinement 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'olex2.solve (Bourhis et al., 2015)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 120(2) _diffrn_crystal_treatment 'flash frozen in gaseous N2' _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean 10.3613 _diffrn_detector_type 'Agilent Diffraction Atlas detector' _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.961 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w 51.00 86.00 1.00 1.00 -- 106.13 -30.00 0.00 35 2 \w 54.00 89.00 1.00 1.00 -- 106.13 -45.00 90.00 35 3 \w 38.00 109.00 1.00 1.00 -- 106.13 -95.00 120.00 71 4 \w 50.00 83.00 1.00 1.00 -- 43.32 -99.00 30.00 33 5 \w 55.00 91.00 1.00 1.00 -- 106.13 -30.00 -90.00 36 6 \w 65.00 90.00 1.00 1.00 -- 106.13 -30.00-180.00 25 7 \w 50.00 89.00 1.00 1.00 -- 106.13 -45.00-180.00 39 8 \w 39.00 104.00 1.00 1.00 -- 106.13 -95.00-150.00 65 9 \w 31.00 85.00 1.00 1.00 -- 106.13 -30.00-120.00 54 10 \w 32.00 82.00 1.00 1.00 -- 106.13 -30.00 -30.00 50 11 \w -49.00 31.00 1.00 1.00 -- -38.50 38.00-150.00 80 12 \w -61.00 -12.00 1.00 1.00 -- -38.50 -57.00 30.00 49 13 \w -37.00 33.00 1.00 1.00 -- -38.50 38.00 -90.00 70 ; _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'SuperNova, Atlas' _diffrn_measurement_method '\w scans' _diffrn_measurement_specimen_support 'MiTeGen micromount' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0021901000 _diffrn_orient_matrix_UB_12 -0.1456334000 _diffrn_orient_matrix_UB_13 0.0079238000 _diffrn_orient_matrix_UB_21 -0.1697838000 _diffrn_orient_matrix_UB_22 0.0041016000 _diffrn_orient_matrix_UB_23 0.0002696000 _diffrn_orient_matrix_UB_31 -0.0313630000 _diffrn_orient_matrix_UB_32 -0.0127608000 _diffrn_orient_matrix_UB_33 -0.0901961000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0244 _diffrn_reflns_av_unetI/netI 0.0245 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.961 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 6146 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.961 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 74.449 _diffrn_reflns_theta_min 4.939 _diffrn_source 'microfocus sealed tube' _diffrn_source_type 'Agilent Diffraction microfocus tube' _exptl_absorpt_coefficient_mu 3.553 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.215 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.534 _exptl_crystal_description block _exptl_crystal_F_000 768 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: diethyl ether, petroleum ether' _exptl_crystal_size_max 0.719 _exptl_crystal_size_mid 0.486 _exptl_crystal_size_min 0.412 _refine_diff_density_max 0.423 _refine_diff_density_min -0.369 _refine_diff_density_rms 0.073 _refine_ls_extinction_coef 0.0046(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2018/1 (Sheldrick 2018)' _refine_ls_goodness_of_fit_ref 1.104 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 210 _refine_ls_number_reflns 3197 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.104 _refine_ls_R_factor_all 0.0307 _refine_ls_R_factor_gt 0.0294 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0465P)^2^+0.7565P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0777 _refine_ls_wR_factor_ref 0.0785 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3110 _reflns_number_total 3197 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4sc03232b2.cif _cod_data_source_block 42a _cod_database_code 1571945 _nottingham_internal_coll_name REARDC _nottingham_internal_coll_number 17201 _nottingham_internal_coll_client REA/RD _nottingham_internal_coll_type custom _nottingham_internal_coll_frame_method '\w scans' _nottingham_internal_coll_frame_time 1.00 _nottingham_internal_coll_frame_width 1.00 _nottingham_internal_coll_user pczwl _nottingham_internal_coll_date 23/08/2017 _nottingham_internal_coll_location NOTTS _nottingham_internal_coll_instrument 'SN, XDA 017-09' _nottingham_internal_process_date 17/11/2017 _nottingham_internal_process_user pczwl _nottingham_internal_solution_date 17/11/2017 _nottingham_internal_solution_user pczwl _nottingham_internal_refinement_date 17/11/2017 _nottingham_internal_refinement_user pczwl _nottingham_internal_validation_date 10/2/2018 _nottingham_internal_validation_user pczwl _nottingham_internal_archive_date 10/2/2018 _shelx_shelxl_version_number 2018/1 _chemical_oxdiff_formula 'C19 H19 Br O' _chemical_oxdiff_usercomment 'REARDC #17201 SN-1190 IN FOMBLIN FILM ON A MICROMOUNT FOR REA/RD' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _reflns_odcompleteness_completeness 99.81 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 67.13 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Ternary CH refined with riding coordinates: C2(H2) 2.b Secondary CH2 refined with riding coordinates: C3(H3A,H3B), C17(H17A,H17B), C21(H21A,H21B) 2.c Aromatic/amide H refined with riding coordinates: C6(H6), C8(H8), C9(H9), C11(H11), C14(H14), C15(H15), C22(H22) 2.d X=CH2 refined with riding coordinates: C23(H23A,H23B) 2.e Idealised Me refined as rotating group: C18(H18A,H18B,H18C) ; _shelx_res_file ; TITL reardc.res created by SHELXL-2018/1 at 22:12:43 on 10-Feb-2018 CELL 1.54184 9.069411 10.532048 17.279853 90 100.1562 90 ZERR 4 0.000296 0.000346 0.000556 0 0.003 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H Br O UNIT 76 76 4 12 L.S. 12 PLAN 20 TEMP -153 conf htab bond $h fmap 2 acta REM REM REM WGHT 0.046500 0.756500 EXTI 0.004602 FVAR 6.12295 O1 4 0.561982 0.347257 0.545866 11.00000 0.02205 0.01317 = 0.02149 -0.00201 0.00362 0.00234 C2 1 0.500560 0.223713 0.526555 11.00000 0.01613 0.01597 = 0.02187 -0.00081 0.00586 0.00045 AFIX 13 H2 2 0.388936 0.231296 0.514801 11.00000 -1.20000 AFIX 0 C3 1 0.542124 0.132977 0.594698 11.00000 0.01951 0.01676 = 0.02073 -0.00010 0.01007 -0.00045 AFIX 23 H3A 2 0.497142 0.048954 0.579595 11.00000 -1.20000 H3B 2 0.499120 0.164364 0.639940 11.00000 -1.20000 AFIX 0 C4 1 0.713973 0.117054 0.620442 11.00000 0.02005 0.01141 = 0.01480 -0.00027 0.00720 -0.00117 C5 1 0.789964 0.246982 0.616423 11.00000 0.02263 0.01194 = 0.01187 -0.00061 0.00910 -0.00061 C6 1 0.939146 0.263584 0.650356 11.00000 0.02305 0.01336 = 0.01337 -0.00099 0.00687 0.00020 AFIX 43 H6 2 0.992612 0.193832 0.676568 11.00000 -1.20000 AFIX 0 C7 1 1.013355 0.378753 0.647393 11.00000 0.02468 0.01717 = 0.01775 -0.00394 0.00825 -0.00353 C8 1 0.933128 0.479612 0.607644 11.00000 0.03165 0.01349 = 0.01959 -0.00139 0.00700 -0.00629 AFIX 43 H8 2 0.981491 0.558929 0.604302 11.00000 -1.20000 AFIX 0 C9 1 0.784403 0.465730 0.573098 11.00000 0.03278 0.01185 = 0.01661 0.00063 0.00567 0.00099 AFIX 43 H9 2 0.731544 0.535127 0.546123 11.00000 -1.20000 AFIX 0 C10 1 0.712076 0.350010 0.577844 11.00000 0.02155 0.01435 = 0.01361 -0.00151 0.00618 -0.00032 C11 1 0.777416 0.027937 0.566245 11.00000 0.01449 0.01493 = 0.01423 -0.00033 0.00549 -0.00310 AFIX 43 H11 2 0.764291 0.048434 0.511922 11.00000 -1.20000 AFIX 0 C12 1 0.850705 -0.077757 0.590954 11.00000 0.01713 0.01314 = 0.01402 -0.00256 0.00690 -0.00168 C13 1 0.874833 -0.121425 0.673683 11.00000 0.02017 0.01485 = 0.01782 0.00263 0.00613 -0.00440 C14 1 0.813514 -0.037443 0.727663 11.00000 0.02770 0.01881 = 0.01256 0.00367 0.00675 -0.00441 AFIX 43 H14 2 0.825191 -0.060434 0.781562 11.00000 -1.20000 AFIX 0 C15 1 0.741865 0.070146 0.703979 11.00000 0.02593 0.01554 = 0.01346 -0.00202 0.00974 -0.00484 AFIX 43 H15 2 0.706107 0.120446 0.742399 11.00000 -1.20000 AFIX 0 O16 4 0.548485 0.174397 0.460098 11.00000 0.02091 0.01559 = 0.01638 -0.00099 0.00326 0.00125 C17 1 0.495011 0.241971 0.387982 11.00000 0.02241 0.02164 = 0.01750 0.00031 -0.00051 0.00025 AFIX 23 H17A 2 0.394204 0.276583 0.389834 11.00000 -1.20000 H17B 2 0.485298 0.181652 0.343429 11.00000 -1.20000 AFIX 0 C18 1 0.596862 0.349301 0.373541 11.00000 0.03385 0.02813 = 0.02023 0.00486 0.00299 -0.00645 AFIX 137 H18A 2 0.588131 0.418974 0.410053 11.00000 -1.50000 H18B 2 0.567965 0.379551 0.319354 11.00000 -1.50000 H18C 2 0.700671 0.319119 0.381835 11.00000 -1.50000 AFIX 0 BR19 3 0.931705 -0.182996 0.519445 11.00000 0.01897 0.01611 = 0.01790 -0.00158 0.00770 0.00238 O20 4 0.939611 -0.220399 0.695473 11.00000 0.03138 0.01802 = 0.02373 0.00747 0.00830 0.00430 C21 1 1.175010 0.396103 0.686667 11.00000 0.02235 0.02248 = 0.02876 -0.00348 0.00791 -0.00417 AFIX 23 H21A 2 1.214548 0.314299 0.709798 11.00000 -1.20000 H21B 2 1.235292 0.421011 0.646617 11.00000 -1.20000 AFIX 0 C22 1 1.191518 0.495892 0.750364 11.00000 0.02260 0.02248 = 0.02646 -0.00338 0.00643 -0.00529 AFIX 43 H22 2 1.148756 0.576992 0.736865 11.00000 -1.20000 AFIX 0 C23 1 1.260975 0.478753 0.823412 11.00000 0.02100 0.03800 = 0.02792 -0.00206 0.00650 -0.00352 AFIX 93 H23A 2 1.305134 0.398923 0.839101 11.00000 -1.20000 H23B 2 1.266807 0.546249 0.860299 11.00000 -1.20000 AFIX 0 HKLF 4 REM REM R1 = 0.0294 for 3110 Fo > 4sig(Fo) and 0.0307 for all 3197 data REM 210 parameters refined using 0 restraints END WGHT 0.0465 0.7565 REM Instructions for potential hydrogen bonds EQIV $1 -x+1, -y, -z+1 HTAB C2 Br19_$1 HTAB C3 O16_$1 HTAB C11 O16 HTAB C18 O1 REM Highest difference peak 0.423, deepest hole -0.369, 1-sigma level 0.073 Q1 1 1.0210 -0.1831 0.5197 11.00000 0.05 0.42 Q2 1 0.7315 0.0878 0.6653 11.00000 0.05 0.40 Q3 1 0.8562 -0.0923 0.6297 11.00000 0.05 0.40 Q4 1 0.9737 -0.1638 0.4526 11.00000 0.05 0.38 Q5 1 0.9511 -0.1415 0.5727 11.00000 0.05 0.38 Q6 1 0.9048 -0.1342 0.4686 11.00000 0.05 0.38 Q7 1 0.9343 -0.2388 0.5613 11.00000 0.05 0.38 Q8 1 0.7415 0.0657 0.5966 11.00000 0.05 0.34 Q9 1 0.9161 -0.2253 0.4716 11.00000 0.05 0.34 Q10 1 1.1864 0.4755 0.7922 11.00000 0.05 0.32 Q11 1 1.1915 0.4427 0.7216 11.00000 0.05 0.32 Q12 1 0.5199 0.1770 0.5609 11.00000 0.05 0.30 Q13 1 0.8396 -0.2000 0.5210 11.00000 0.05 0.30 Q14 1 0.7444 0.3042 0.6054 11.00000 0.05 0.29 Q15 1 0.5235 0.2099 0.4294 11.00000 0.05 0.29 Q16 1 1.2714 0.5187 0.7778 11.00000 0.05 0.29 Q17 1 0.7568 0.1769 0.6181 11.00000 0.05 0.27 Q18 1 0.6300 0.3400 0.5579 11.00000 0.05 0.27 Q19 1 0.6290 0.1204 0.6056 11.00000 0.05 0.27 Q20 1 0.7458 0.0013 0.7055 11.00000 0.05 0.26 ; _shelx_res_checksum 55227 _shelx_hkl_file ; 0 0 -3 243.216 39.3168 13 0 0 -3 139.247 32.2573 11 0 0 -4 4759.72 181.494 11 0 0 -4 5231.36 192.433 13 0 0 -5 231.197 53.0262 11 0 0 -5 101.909 54.3309 4 0 0 -6 73795.6 1079.34 4 0 0 -6 80650.5 880.960 11 0 0 -7 1808.17 149.421 11 0 0 -7 75.2026 63.5805 4 0 0 -8 34066.3 650.116 11 0 0 -8 24693.2 761.966 4 0 0 -9 287.733 113.063 4 0 0 -10 49313.1 1193.24 4 0 0 10 45477.8 1210.02 12 0 0 -11 141.843 114.418 4 0 0 -12 4053.24 398.401 4 0 0 -12 3781.97 452.069 8 0 0 -12 4515.16 475.342 3 0 0 -13 208.673 166.800 8 0 0 -13 126.057 108.385 4 0 0 -14 53282.6 1833.49 8 0 0 -14 44172.9 1611.00 3 0 0 -15 591.628 234.216 8 0 0 -15 825.616 250.464 3 0 0 -16 8667.25 731.920 3 0 0 -16 9585.94 807.965 8 0 0 -17 219.206 183.813 3 0 0 -17 175.759 170.457 8 0 0 -18 38981.0 1385.01 3 0 0 -18 39583.0 1396.52 8 0 0 -19 173.270 143.738 3 0 0 -19 167.162 128.615 8 0 0 -20 39054.4 1057.07 3 0 1 0 81.4471 21.1004 13 0 1 1 130688. 771.802 12 0 1 -1 132030. 889.453 11 0 1 -2 9724.70 273.656 11 0 1 2 8940.85 233.407 12 0 1 -3 22988.7 462.377 13 0 1 -3 21923.5 455.501 11 0 1 -4 7606.21 298.443 11 0 1 4 7292.07 268.595 12 0 1 -5 205386. 1678.35 4 0 1 -5 201494. 1579.82 13 0 1 -6 217775. 1853.36 4 0 1 -6 210325. 1862.65 11 0 1 -7 1052.31 144.150 11 0 1 -7 965.311 152.832 4 0 1 7 1425.28 170.273 12 0 -1 -8 118366. 1642.81 4 0 1 -8 116527. 1616.01 4 0 -1 -9 27112.1 861.783 4 0 1 -9 24785.2 786.940 4 0 1 -9 25340.8 734.963 11 0 -1 -10 156710. 2196.73 4 0 1 -10 125349. 1819.73 4 0 -1 -11 10800.8 630.063 4 0 -1 -12 259732. 3249.65 4 0 -1 -12 220328. 3240.76 8 0 -1 -12 218799. 3176.93 3 0 1 -12 244827. 3469.49 3 0 1 -12 247182. 3707.26 8 0 -1 -13 76.0099 92.2589 4 0 1 -13 29.6168 136.310 8 0 -1 -13 47.3062 105.634 3 0 1 -13 161.306 146.007 3 0 1 -14 79870.0 2165.35 3 0 -1 -14 84204.2 2227.27 8 0 1 -15 11422.9 831.335 3 0 -1 -15 11414.0 801.779 3 0 1 -15 11266.9 903.102 8 0 -1 -15 11524.0 846.432 8 0 1 -16 42892.4 1691.54 8 0 -1 -16 42757.5 1591.89 8 0 1 -16 39549.1 1554.08 3 0 -1 -16 38362.0 1459.18 3 0 1 -17 2667.28 416.173 3 0 -1 -17 1617.57 333.893 8 0 -1 -17 2002.69 335.941 3 0 1 -17 1762.99 352.721 8 0 1 -18 51855.4 1575.90 8 0 1 -18 55482.9 1645.97 3 0 -1 -18 52119.5 1510.14 3 0 -1 -18 50073.2 1545.31 8 0 1 -19 5847.88 456.186 8 0 1 -19 5911.79 498.160 3 0 1 -20 10253.8 554.840 3 0 2 0 192659. 1315.59 11 0 2 -1 132881. 1160.83 11 0 2 -1 130263. 1133.14 13 0 2 -2 467340. 2292.92 13 0 2 -2 458371. 2331.20 11 0 -2 -3 70044.6 437.409 13 0 2 3 71209.1 837.334 12 0 2 -3 70726.7 959.105 13 0 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4662.74 392.279 8 0 2 -20 6619.26 436.860 3 0 3 0 149.563 62.7156 11 0 3 1 366557. 2143.12 11 0 3 -1 387163. 2366.51 11 0 3 -2 80488.5 1135.27 11 0 3 -3 423367. 2731.31 11 0 3 -4 7109.15 373.201 11 0 3 -5 161068. 1807.38 11 0 3 -6 52200.4 1103.20 11 0 3 6 51865.4 964.300 12 0 3 7 153393. 1770.27 12 0 3 -7 153860. 2027.99 11 0 3 8 1041.76 158.823 12 0 3 -8 1005.39 192.926 11 0 3 -9 89098.6 1700.96 11 0 3 9 89797.3 1429.61 12 0 3 -10 6109.42 459.350 11 0 3 -11 38041.4 1581.63 8 0 3 -11 34396.9 1134.45 11 0 -3 -11 38220.4 1280.18 4 0 3 -11 37414.1 1305.76 3 0 -3 -11 41591.5 1357.60 8 0 -3 -12 26497.8 1135.71 8 0 3 -12 26967.4 1164.32 3 0 3 -12 27999.5 1410.66 8 0 3 -12 28123.0 1130.95 2 0 3 -13 22837.0 1295.42 8 0 -3 -13 25259.7 1146.20 8 0 3 -13 25065.7 1163.30 3 0 -3 -13 24781.6 1143.14 4 0 -3 -14 5126.01 546.777 4 0 3 -14 7089.33 724.444 8 0 3 -14 6658.81 621.425 3 0 3 -15 33643.8 1340.38 3 0 -3 -15 36452.5 1421.89 8 0 3 -15 31416.0 1477.29 8 0 3 -16 26755.3 1192.52 3 0 3 -16 25216.2 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168.271 3 3 3 -15 675.868 298.643 8 3 -3 -15 129.391 196.475 8 3 -3 -14 137785. 2877.03 8 3 3 -14 137544. 2673.84 3 3 -3 -13 6133.74 617.700 8 3 3 -13 5603.15 645.130 8 3 3 -13 6285.33 578.621 3 3 3 -12 200029. 2902.72 13 3 3 -12 191256. 3586.64 8 3 3 -11 15098.1 825.678 3 3 -3 -11 14758.2 853.376 8 3 3 -11 12519.0 880.834 8 3 3 -11 13233.6 750.617 13 3 -3 -11 14998.4 847.474 7 3 -3 -10 45692.3 1427.81 8 3 3 -10 41566.4 1316.09 3 3 3 -10 40046.2 1247.38 13 3 3 -10 44015.8 1192.04 11 3 3 -9 81705.2 1576.77 11 3 3 -9 80009.8 1705.79 13 3 3 -8 15128.2 707.461 13 3 3 -8 15956.1 689.860 11 3 3 -7 11974.9 611.830 13 3 3 -6 1946.33 248.523 13 3 3 -5 14770.2 629.636 13 3 3 -4 4616.25 346.834 13 3 3 -3 37067.9 930.115 13 3 3 -2 27359.2 776.575 13 -3 3 2 26257.1 743.616 11 3 3 -1 83325.9 1316.43 12 -3 3 1 80748.5 1349.73 11 3 3 -1 82362.3 1321.61 13 3 3 0 235.232 91.2287 13 -3 3 0 335.510 113.565 11 3 3 0 200.382 100.484 12 3 3 1 576.595 118.967 13 -3 3 -1 958.967 174.150 11 3 3 1 649.722 149.106 12 3 3 2 74784.8 1179.63 13 -3 3 -2 75376.7 1408.52 11 3 3 2 71982.6 1386.73 12 3 3 3 41863.9 870.790 13 -3 3 -3 38888.2 1062.71 11 3 3 4 102754. 1858.85 12 -3 3 -4 94995.6 1700.55 11 3 3 5 7457.40 547.909 12 -3 3 -5 6607.05 474.516 11 -3 3 -6 63360.5 1498.28 11 3 3 6 67013.1 1687.74 12 -3 3 -7 4875.43 445.120 11 3 3 7 5368.15 511.690 12 -3 3 -8 20051.0 914.418 3 3 3 8 20673.6 1005.28 12 -3 3 -8 19820.6 907.806 11 -3 -3 -9 5711.49 521.703 4 3 3 9 6568.93 588.273 12 -3 3 -9 5627.91 510.360 11 -3 3 -9 6925.74 553.942 3 -3 -3 -10 161494. 2825.48 4 -3 3 -10 160890. 2730.10 3 -3 -3 -11 2763.01 392.463 4 3 3 11 2220.39 358.292 12 -3 3 -11 1786.06 314.783 3 -3 -3 -12 92576.2 2262.53 4 -3 3 -12 71333.7 1845.86 3 -3 3 -13 21771.3 1040.37 3 -3 3 -14 87706.5 2033.25 3 -3 3 -15 13989.8 810.332 3 -3 3 -16 88427.7 1875.24 3 -3 3 -17 300.693 150.718 3 -3 3 -18 53907.7 1165.95 3 3 4 -20 31504.2 909.846 8 3 4 -19 10555.6 657.472 8 3 4 -18 4317.85 502.882 8 3 4 -17 3185.65 470.140 8 3 4 -16 3530.36 444.395 3 3 4 -16 3382.14 518.422 8 3 -4 -15 0.34027 228.530 8 3 4 -15 180.390 225.629 8 3 -4 -14 30364.5 1363.33 8 3 4 -14 30411.4 1504.76 8 3 4 -14 28629.7 1219.74 3 3 4 -13 29.5314 148.294 3 3 -4 -13 12.5953 184.197 8 3 4 -13 126.260 177.528 8 3 -4 -12 25025.2 1188.60 8 3 4 -12 26244.0 1130.57 3 3 4 -12 25167.7 1324.34 8 3 4 -11 9886.10 809.730 8 3 4 -11 10135.2 692.040 3 3 -4 -11 10378.1 746.246 8 3 4 -11 9557.98 651.839 13 3 -4 -10 22887.3 1048.98 8 3 4 -10 23659.4 1014.19 3 3 4 -10 23517.2 1009.48 13 3 4 -10 23181.5 919.004 11 3 -4 -10 23333.6 1134.68 9 3 -4 -9 23122.4 1012.50 8 3 4 -9 23624.0 979.368 3 3 4 -9 22180.3 991.797 2 3 4 -9 22435.8 951.764 13 3 4 -9 23359.9 914.285 11 3 4 -8 81375.1 1783.33 13 3 4 -8 78946.4 1652.36 11 3 4 -7 342.558 141.816 13 3 4 -7 150.238 105.775 11 3 4 -6 265101. 2927.46 13 3 4 -5 145110. 2085.24 13 3 4 -4 211013. 2463.40 13 3 4 -3 3288.26 307.921 13 -3 4 3 4192.51 307.123 11 -3 4 2 343045. 2857.17 11 3 4 -2 330023. 2923.14 13 -3 4 1 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1102.01 7 8 -5 -7 1950.01 356.614 9 8 5 -7 2600.56 354.052 7 8 -5 -6 9812.81 736.055 9 8 5 -6 9533.04 645.932 7 8 -5 -5 74471.9 1974.36 9 8 -5 -4 1247.79 285.057 9 -8 -5 4 1383.84 257.778 10 8 -5 -3 27387.7 1160.10 9 -8 -5 3 26289.4 1073.49 10 8 -5 -2 13210.4 775.454 9 -8 -5 2 12107.5 743.946 10 8 -5 -1 27093.0 1061.68 9 -8 -5 1 24607.2 1060.68 10 -8 -5 0 14853.4 834.654 10 -8 -5 -1 68074.6 1740.90 10 -8 -5 -2 376.038 210.129 10 -8 -5 -3 48393.8 1416.49 10 -8 5 -4 9551.87 528.969 3 -8 -5 -4 10095.7 639.277 10 -8 5 -5 62156.0 1295.40 3 -8 -5 -5 64364.7 1502.99 10 -8 -5 -5 65233.5 1531.89 1 -8 -5 -6 217.855 135.732 1 -8 5 -6 240.135 97.0071 3 -8 -5 -7 5509.31 400.425 1 -8 5 -7 5379.43 341.893 3 -8 -5 -8 9359.91 464.311 1 -8 5 -8 9044.04 398.794 3 -8 5 -9 10508.0 379.172 3 8 6 -14 23936.2 693.218 7 8 6 -13 30897.5 886.486 7 8 -6 -13 29939.8 839.894 9 8 6 -12 2292.17 272.502 7 8 -6 -12 2533.71 292.410 9 8 6 -11 43714.3 1210.20 7 8 -6 -11 46739.1 1302.75 9 8 -6 -10 819.327 220.699 9 8 6 -10 839.323 195.533 7 8 6 -9 39037.9 1207.36 7 8 -6 -9 41719.5 1338.20 9 8 6 -8 19477.6 863.103 7 8 -6 -8 21076.1 969.371 9 8 6 -7 14813.2 750.485 7 8 -6 -7 15390.3 846.499 9 8 6 -6 3343.59 361.658 7 8 -6 -6 4232.00 458.343 9 8 -6 -5 9367.60 660.960 9 -8 -6 4 52349.5 1342.81 10 8 -6 -4 51732.9 1503.06 9 -8 -6 3 19810.1 874.698 10 8 -6 -3 21420.9 953.899 9 -8 -6 2 64308.2 1586.72 10 8 -6 -2 68375.6 1624.56 9 -8 -6 1 28639.1 1075.80 10 8 -6 -1 29786.4 1036.51 9 -8 -6 0 99266.2 1983.66 10 -8 -6 -1 5309.50 477.197 10 -8 -6 -2 80972.7 1745.66 10 -8 -6 -3 1012.50 229.844 10 -8 -6 -4 64961.4 1466.98 10 -8 -6 -5 3634.19 341.972 10 -8 -6 -6 3382.10 315.230 1 -8 -6 -7 9491.79 464.225 1 8 7 -12 60552.5 1085.72 7 8 -7 -12 60244.0 1116.68 9 8 7 -11 1540.75 198.165 7 8 -7 -11 1434.23 212.127 9 8 7 -10 91642.3 1528.68 7 8 -7 -10 98004.0 1728.42 9 8 7 -9 26330.0 853.325 7 8 -7 -9 26763.3 952.433 9 8 7 -8 71286.5 1421.21 7 8 -7 -8 76735.2 1663.01 9 8 7 -7 2486.96 277.025 7 8 -7 -7 2703.88 338.120 9 8 -7 -6 66900.2 1572.38 9 8 -7 -5 11434.0 660.949 9 8 -7 -4 18775.5 827.970 9 -8 -7 3 1828.08 250.393 10 8 -7 -3 2388.60 297.553 9 -8 -7 2 16709.0 734.767 10 8 -7 -2 18452.8 755.768 9 -8 -7 1 2719.21 314.046 10 -8 -7 0 1356.14 235.446 10 -8 -7 -1 504.206 166.356 10 -8 -7 -2 7045.47 478.154 10 -8 -7 -3 750.896 174.216 10 -8 -7 -4 2020.79 248.598 10 -8 -7 -5 147.716 101.253 1 -8 -7 -5 99.7023 101.502 10 -8 -7 -6 5124.06 321.882 1 8 -8 -10 406.386 99.9651 9 8 -8 -9 11222.1 514.754 9 8 -8 -8 320.084 113.314 9 8 -8 -7 1160.37 197.126 9 8 -8 -6 28418.1 880.667 9 8 -8 -5 11045.2 549.683 9 8 -8 -4 37627.6 976.222 9 -8 -8 3 11859.0 482.947 10 8 -8 -3 10694.0 499.123 9 -8 -8 2 82525.1 1363.32 10 -8 -8 1 1750.01 217.203 10 -8 -8 0 33486.1 903.882 10 -8 -8 -1 2949.39 279.083 10 -8 -8 -2 30642.5 834.632 10 -8 -8 -3 3475.31 280.244 10 -8 -8 -4 31866.5 758.287 10 -8 -8 -4 32434.2 782.310 1 9 0 -15 32541.0 869.017 6 9 0 -14 261.121 123.788 6 9 0 -13 26116.4 1013.26 7 9 0 -13 27256.2 1031.95 6 9 0 -12 95.0538 128.730 7 9 0 -12 375.779 187.286 6 9 0 -11 7504.32 594.019 7 9 0 -11 7601.33 629.386 6 9 0 -10 154.173 156.035 7 9 0 -10 679.719 245.539 6 9 0 -9 1161.74 263.020 7 9 0 -9 478.308 217.289 6 9 0 -8-22.4578 135.698 7 9 0 -8 585.003 232.879 6 9 0 -7 55.4870 112.051 7 9 0 -7 419.884 214.816 6 9 0 -6 339.272 131.284 7 9 0 -6 779.523 240.865 6 9 0 -5 9226.46 718.277 6 -9 0 4 194.409 136.993 1 9 0 -4 405.757 186.018 6 -9 0 3 260.314 158.481 1 9 0 -3 385.227 181.721 6 -9 0 2 51.4570 147.631 1 9 0 -2 231.656 128.992 6 -9 0 1 42706.3 1390.24 1 -9 0 0 108.447 154.408 1 -9 0 -1 49081.4 1474.63 1 -9 0 -2-43.4456 164.926 1 -9 0 -3 39306.5 1276.08 1 -9 0 -4 86.7752 155.748 1 -9 0 -5 63175.7 1487.33 1 -9 0 -6 85.7325 132.878 1 -9 0 -7 81725.6 1591.23 3 -9 0 -7 88148.2 1565.07 1 -9 0 -8 47.5861 100.559 3 -9 0 -9 112673. 1493.18 3 9 1 -15 5951.87 374.278 6 9 1 -14 102.486 97.0896 7 9 -1 -14 510.164 155.717 6 9 1 -14 281.752 129.804 6 9 -1 -13 18436.3 810.334 9 9 1 -13 18354.4 839.556 7 9 -1 -13 16213.0 803.424 6 9 1 -13 17111.1 825.331 6 9 1 -12 9723.60 653.186 7 9 -1 -12 9106.06 649.120 6 9 1 -12 9793.41 675.909 6 9 1 -11 87716.1 1975.49 7 9 -1 -11 91825.3 2096.43 6 9 1 -11 87512.0 2082.16 6 9 -1 -10 9993.57 709.674 7 9 1 -10 10259.7 708.540 7 9 -1 -10 10378.3 751.177 6 9 1 -10 10433.7 767.605 6 9 -1 -9 45110.7 1478.92 7 9 1 -9 47878.0 1506.98 7 9 -1 -9 48468.4 1621.52 6 9 1 -8 95.9228 147.881 7 9 -1 -8 49.0759 191.556 6 9 1 -7 20008.5 961.401 7 9 -1 -7 17353.5 993.174 6 9 1 -6-20.7854 125.015 7 9 -1 -6 294.622 199.739 6 9 -1 -5 113962. 2452.01 6 -9 1 4 13534.3 766.572 1 9 -1 -4 13218.2 834.279 6 9 1 -4 14535.8 884.302 6 -9 -1 4 14609.0 782.958 1 -9 -1 3 96646.5 2050.93 1 -9 1 3 96020.1 2064.23 1 9 -1 -3 99551.4 2203.28 6 9 1 -3 102805. 2216.83 6 -9 -1 2 13139.2 786.826 1 -9 1 2 13770.5 794.450 1 9 -1 -2 14421.2 821.578 6 9 1 -2 15175.7 820.934 6 -9 -1 1 34217.4 1245.55 1 -9 1 1 35460.0 1260.17 1 -9 -1 0 3615.52 428.322 1 -9 1 0 4219.43 454.104 1 -9 -1 -1 8810.34 640.246 1 -9 1 -1 7327.64 582.165 1 -9 -1 -2 3507.78 416.986 1 -9 1 -2 3886.88 433.088 1 -9 -1 -3 9776.08 644.074 1 -9 1 -3 9442.14 638.674 1 -9 1 -4 6099.87 505.136 1 -9 -1 -4 5894.90 500.273 1 -9 1 -5 10298.8 620.568 1 -9 -1 -5 10170.2 608.784 1 -9 -1 -6 9598.23 556.111 1 -9 -1 -7 664.850 158.755 1 -9 1 -7 408.903 144.693 3 -9 -1 -7 538.304 154.109 3 -9 -1 -8 22094.6 710.784 1 -9 -1 -8 21066.2 723.093 3 -9 1 -8 22447.2 749.254 3 -9 -1 -9 1220.06 157.158 3 -9 1 -9 1398.08 176.780 3 9 2 -15 4686.94 339.302 7 9 2 -14 56789.0 1321.40 7 9 2 -14 56981.7 1294.21 6 9 -2 -13 4362.41 391.136 9 9 2 -13 4054.75 391.232 7 9 2 -13 3598.31 388.809 6 9 -2 -12 25102.4 1020.66 9 9 2 -12 26874.9 1029.78 7 9 -2 -12 28166.2 1079.00 6 9 2 -12 28897.0 1130.23 6 9 2 -11 4882.39 470.160 7 9 -2 -11 5527.21 523.078 6 9 2 -10 7831.65 607.209 7 9 -2 -10 8904.56 687.901 6 9 2 -9 17281.3 887.379 7 9 -2 -9 18728.5 1005.40 6 9 2 -8 8325.73 619.971 7 9 -2 -8 8275.42 693.581 6 9 2 -7 74.7928 135.344 7 9 -2 -7 54.6648 176.509 6 9 2 -6 38207.8 1255.99 7 9 -2 -6 36281.0 1392.57 6 9 -2 -5 3322.91 433.421 6 -9 -2 4 45174.9 1351.26 1 9 -2 -4 44241.8 1506.85 6 -9 -2 3 4939.63 472.642 1 9 -2 -3 4760.47 491.767 6 -9 -2 2 29428.3 1144.88 1 -9 2 1 26718.1 1119.26 1 -9 -2 1 26036.4 1080.27 1 -9 2 0 43826.8 1405.94 1 -9 -2 0 42069.0 1357.81 1 -9 2 -1 54455.6 1554.67 1 -9 -2 -1 51590.6 1496.54 1 -9 2 -2 21013.9 966.815 1 -9 -2 -2 20944.1 948.894 1 -9 -2 -3 17544.2 850.844 1 -9 2 -3 18722.7 892.016 1 -9 -2 -4 2960.63 362.215 1 -9 -2 -5 44493.5 1228.17 1 -9 -2 -6 214.953 130.835 1 -9 2 -7 18137.5 696.833 3 -9 -2 -7 18508.0 698.070 3 -9 -2 -7 20046.0 716.224 1 -9 -2 -8 3450.28 275.117 1 -9 2 -8 3278.37 280.379 3 -9 2 -9 6848.20 345.574 3 9 3 -15 13920.2 519.636 7 9 3 -14 16875.2 667.666 7 9 3 -14 16061.4 642.565 6 9 3 -13 5703.70 434.298 7 9 3 -13 6277.17 473.230 6 9 -3 -13 5617.74 414.055 9 9 -3 -12 49692.5 1331.06 9 9 3 -12 48616.6 1316.32 7 9 -3 -11 40636.9 1305.05 9 9 3 -11 37441.4 1190.56 7 9 -3 -10 28636.5 1156.25 9 9 3 -10 26636.3 1039.09 7 9 -3 -10 28881.0 1146.68 6 9 -3 -9 1921.03 350.010 9 9 3 -9 1694.63 283.071 7 9 -3 -9 2641.44 383.672 6 9 3 -8 295.697 140.844 7 9 -3 -8 298.452 202.879 6 9 3 -7 7761.11 569.647 7 9 -3 -7 7933.53 651.376 6 9 -3 -6 7517.25 635.983 6 9 -3 -5 1180.87 278.873 6 -9 -3 4 8155.98 568.425 1 -9 -3 3 2979.53 356.169 1 -9 -3 2 33433.4 1187.09 1 9 -3 -1 21011.6 918.679 9 -9 -3 1 19138.0 916.953 1 -9 -3 0 47964.7 1423.19 1 -9 -3 -1 755.205 223.841 1 -9 -3 -2 43487.9 1323.21 1 -9 -3 -3 7501.55 548.494 1 -9 -3 -4 69211.1 1548.53 1 -9 -3 -5 2228.24 289.402 1 -9 -3 -6 47158.1 1132.58 1 -9 3 -6 45191.7 1080.69 3 -9 -3 -7 1470.16 200.085 1 -9 3 -7 1336.27 187.223 3 -9 -3 -8 35406.0 780.586 1 -9 3 -8 34088.6 777.138 3 9 4 -14 16102.1 571.384 7 9 4 -13 1853.85 228.415 7 9 4 -13 1850.93 245.823 6 9 -4 -13 1870.60 226.191 9 9 4 -12 47875.3 1191.33 7 9 -4 -12 49425.1 1231.55 9 9 4 -11 5841.79 447.346 7 9 -4 -11 6306.84 489.213 9 9 -4 -10 34974.9 1180.61 9 9 4 -10 32412.3 1062.58 7 9 -4 -9 4333.21 460.663 9 9 4 -9 4078.78 398.922 7 9 -4 -8 53692.4 1553.13 9 9 4 -8 50620.2 1346.62 7 9 -4 -7 1098.42 273.891 9 9 4 -7 1120.40 217.188 7 9 -4 -6 49295.5 1515.59 9 9 -4 -5 9784.65 684.161 9 9 -4 -4 24298.2 1048.72 9 -9 -4 4 25144.6 938.924 1 9 -4 -3 2555.23 346.524 9 -9 -4 3 1911.71 285.168 1 9 -4 -2 74181.5 1691.14 9 -9 -4 2 73103.8 1673.05 1 9 -4 -1 2051.70 276.332 9 -9 -4 1 2048.52 306.164 1 -9 -4 0 38798.8 1223.06 1 -9 -4 -1 3686.56 396.089 1 -9 -4 -2 32033.2 1074.45 1 -9 -4 -3 239.896 158.157 1 -9 4 -4 9558.07 501.604 3 -9 -4 -4 10775.0 588.142 1 -9 4 -5 1067.47 170.681 3 -9 -4 -5 1087.27 199.770 1 -9 -4 -6 765.966 156.999 1 -9 4 -6 741.923 132.975 3 -9 -4 -7 1196.47 162.081 1 -9 4 -7 1138.24 141.963 3 9 5 -12 11548.8 505.998 7 9 -5 -12 11916.5 541.366 9 9 5 -11 26270.3 815.142 7 9 -5 -11 28478.1 918.827 9 9 -5 -10 323.254 145.040 9 9 5 -10 95.1011 83.8206 7 9 5 -9 49821.4 1192.09 7 9 -5 -9 59469.6 1464.67 9 9 5 -8 8349.25 494.196 7 9 -5 -8 8136.94 566.878 9 9 -5 -7 40035.5 1250.91 9 9 -5 -6 614.280 191.565 9 9 -5 -5 706.383 189.097 9 -9 -5 4 23515.3 843.233 1 9 -5 -4 23728.4 944.692 9 -9 -5 3 13914.8 679.787 1 9 -5 -3 14405.0 710.475 9 -9 -5 2 2897.58 328.876 1 9 -5 -2 3284.29 329.159 9 -9 -5 1 4180.89 394.044 1 -9 -5 0 17184.7 777.688 1 -9 -5 -1 8998.46 554.651 1 -9 5 -2 37791.6 871.593 3 -9 -5 -2 38105.1 1101.41 1 -9 5 -3 10448.3 445.997 3 -9 -5 -3 10181.1 557.750 1 -9 -5 -4 47335.9 1129.17 1 -9 5 -4 43931.3 846.164 3 -9 5 -5 433.077 87.8819 3 -9 -5 -5 770.971 157.757 1 -9 -5 -6 52991.3 1008.06 1 9 -6 -11 8274.18 419.258 9 9 -6 -10 33041.0 919.588 9 9 -6 -9 10189.0 550.751 9 9 -6 -8 13078.0 637.845 9 9 -6 -7 273.188 129.034 9 9 -6 -6 17167.2 753.511 9 9 -6 -5 674.518 159.757 9 9 -6 -4 16091.6 694.734 9 -9 -6 4 14917.9 596.475 1 -9 -6 3 3077.80 291.517 1 9 -6 -3 3439.38 312.366 9 -9 -6 2 17229.6 696.668 1 -9 -6 1 743.509 166.196 1 -9 -6 0 16672.0 688.039 1 -9 -6 -1 7318.03 452.120 1 -9 -6 -2 1337.78 205.128 1 -9 -6 -3 39368.4 963.623 1 -9 -6 -4 10156.0 466.046 1 -9 -6 -5 19397.9 576.310 1 9 -7 -9 49974.8 961.577 9 9 -7 -8 4361.02 308.692 9 9 -7 -7 100517. 1483.03 9 9 -7 -6 2000.76 224.266 9 9 -7 -5 64934.3 1168.40 9 9 -7 -4 855.318 140.221 9 -9 -7 3 19619.0 589.794 1 -9 -7 2 308.751 98.4117 1 -9 -7 1 46863.4 982.780 1 -9 -7 0 13382.0 526.553 1 -9 -7 -1 15480.0 558.318 1 -9 -7 -2 1242.38 160.527 1 -9 -7 -3 2256.71 198.137 1 10 0 -13 77.4003 70.0982 6 10 0 -12 47260.4 1092.57 9 10 0 -12 48366.1 1172.07 6 10 0 -11 164.091 122.032 6 10 0 -10 53870.2 1403.01 6 10 0 -9 403.923 160.202 6 10 0 -8 58364.3 1534.13 6 10 0 -7 577.230 189.717 6 10 0 -6 1025.90 224.908 6 10 0 -5 446.290 168.846 6 10 0 -4 2904.78 330.556 6 -10 0 3 162.565 92.8729 1 -10 0 2 730.470 178.520 1 -10 0 1 10.6794 87.4351 1 -10 0 0 12177.5 647.444 1 -10 0 -1 118.877 116.926 1 -10 0 -2 37108.0 1073.08 1 -10 0 -3-28.7042 102.127 1 -10 0 -4 22215.0 768.859 1 -10 0 -6 21952.9 634.527 3 10 1 -13 6835.82 385.481 6 10 -1 -12 10879.0 526.859 9 10 1 -12 9931.30 529.188 6 10 -1 -11 2786.92 307.791 9 10 -1 -11 2847.07 322.691 6 10 1 -11 2457.33 298.683 6 10 -1 -10 40066.8 1199.57 6 10 1 -10 39445.6 1175.72 6 10 -1 -9 6999.71 528.746 6 10 1 -9 6707.26 515.727 6 10 -1 -8 44992.3 1342.08 6 10 1 -8 45819.3 1334.04 6 10 -1 -7 6528.91 530.890 6 10 1 -7 6789.08 532.327 6 10 -1 -6 80734.5 1783.21 6 10 1 -6 79383.6 1755.78 6 10 -1 -5 2723.32 344.149 6 10 1 -5 3151.67 354.713 6 10 -1 -4 101609. 1868.58 6 10 1 -4 100110. 1861.48 6 -10 -1 3 790.248 180.637 1 -10 -1 2 61715.3 1421.07 1 -10 -1 1 1871.48 263.604 1 -10 -1 0 41145.1 1163.09 1 -10 -1 -1 20392.8 803.774 1 -10 -1 -2 25675.7 878.024 1 -10 -1 -3 695.863 169.155 1 -10 -1 -4 17323.3 664.725 1 -10 1 -5 6494.42 382.845 3 -10 -1 -5 5887.81 363.362 3 -10 -1 -5 7058.25 403.148 1 -10 1 -6 506.943 108.390 3 10 -2 -12 5776.57 367.102 9 10 2 -12 6041.60 392.529 6 10 -2 -11 19951.2 753.417 9 10 2 -11 17967.7 730.231 6 10 -2 -10 24931.7 910.500 9 10 2 -10 23922.8 887.448 6 10 -2 -9 53301.1 1382.78 9 10 2 -9 48875.8 1305.16 6 10 2 -8 20155.0 861.384 6 10 2 -7 51336.5 1372.93 6 10 2 -6 9432.13 599.059 6 10 2 -5 39196.9 1157.79 6 10 2 -4 634.517 158.721 6 -10 -2 3 77562.4 1490.94 1 -10 -2 2 862.738 184.573 1 -10 -2 1 22660.1 848.396 1 -10 -2 0 1911.74 263.312 1 -10 -2 -1 11751.6 600.983 1 -10 -2 -2 4784.01 379.120 1 -10 -2 -3 8477.04 478.102 1 -10 -2 -4 40464.2 969.277 1 -10 2 -5 1640.25 184.985 3 -10 -2 -5 1756.64 179.009 3 -10 -2 -5 1584.53 193.876 1 -10 2 -6 16263.8 488.816 3 10 3 -12 2549.28 235.089 6 10 3 -11 63932.8 1256.44 6 10 -3 -11 65667.8 1255.74 9 10 -3 -10 25701.9 866.669 9 10 3 -10 23198.5 673.131 7 10 3 -10 23728.9 832.388 6 10 -3 -9 10731.4 592.501 9 10 3 -9 11767.2 613.859 6 10 -3 -8 10582.3 604.654 9 10 3 -8 10067.9 585.092 6 10 -3 -7 14167.3 717.714 9 10 3 -7 14729.8 707.983 6 10 -3 -6 26857.3 979.162 9 10 3 -6 25614.7 911.944 6 10 -3 -5 10554.4 617.454 9 10 3 -5 9949.39 554.780 6 10 -3 -4 513.847 161.165 9 10 -3 -3 2644.59 288.983 9 -10 -3 3 2452.37 266.056 1 10 -3 -2 1563.95 214.673 9 -10 -3 2 1550.87 219.915 1 -10 -3 1 14921.7 655.743 1 -10 -3 0 8982.05 512.622 1 -10 -3 -1 12952.7 600.804 1 -10 -3 -2 5640.85 391.636 1 -10 -3 -3 33541.3 890.546 1 -10 3 -4 112.837 61.1503 3 -10 -3 -4 134.761 91.4630 1 -10 -3 -5 24143.5 636.635 1 10 -4 -10 169.281 92.1160 9 10 4 -10 330.415 103.369 6 10 4 -9 66723.2 1302.95 6 10 -4 -9 67822.5 1330.59 9 10 4 -8 4416.30 359.256 6 10 -4 -8 4242.49 354.169 9 10 4 -7 91698.1 1592.14 6 10 -4 -7 96643.3 1668.69 9 10 -4 -6 663.054 174.566 9 10 4 -6 951.358 171.610 6 10 4 -5 87263.0 1455.20 6 10 -4 -5 90897.7 1586.73 9 10 -4 -4 744.404 153.375 9 -10 -4 3 34524.8 867.726 1 10 -4 -3 29235.3 824.741 9 -10 -4 2 4359.09 324.443 1 -10 -4 1 64692.5 1254.25 1 -10 -4 0 3465.78 301.770 1 -10 -4 -1 23024.2 740.431 1 -10 4 -2 5149.99 283.313 3 -10 -4 -2 5766.77 360.047 1 -10 -4 -3 18237.2 596.980 1 -10 -4 -4 24494.9 632.932 1 10 -5 -9 35713.3 825.164 9 10 5 -8 17574.3 583.762 6 10 -5 -8 19020.8 636.416 9 10 5 -7 13181.7 507.659 6 10 -5 -7 13223.1 546.477 9 10 -5 -6 24931.0 743.307 9 10 -5 -5 306.804 98.6594 9 10 -5 -4 13104.4 500.577 9 -10 -5 2 10990.2 442.643 1 -10 -5 1 481.671 102.101 1 -10 -5 0 455.711 104.982 1 -10 -5 -1 3993.44 270.688 1 -10 -5 -2 7435.25 352.399 1 11 -1 -8 6556.77 368.428 9 11 -1 -7 2534.04 243.498 9 11 -1 -6 5298.36 347.993 9 11 -1 -5 5160.87 334.633 9 11 -1 -4 2480.71 224.727 9 11 -2 -6 3114.64 244.430 9 0 0 0 0.00 0.00 0 TITL REARDC in P2(1)/n REM P2(1)/n (#14 in standard setting) CELL 1.54184 9.069411 10.532048 17.279853 90.0000 100.1562 90.0000 ZERR 4.00 0.000296 0.000346 0.000556 0.0000 0.0030 0.0000 LATT 1 SYMM -x+1/2, y+1/2,-z+1/2 SFAC C H O Br UNIT 76.00 76.00 4.00 4.00 TREF HKLF 4 END ; _shelx_hkl_checksum 60748 _olex2_exptl_crystal_mounting_method "'in fomblin film on a micromount" _olex2_submission_original_sample_id RA-174-002 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.290 _oxdiff_exptl_absorpt_empirical_full_min 0.817 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.56198(16) 0.34726(13) 0.54587(8) 0.0189(3) Uani 1 1 d . . . . . C2 C 0.5006(2) 0.22371(19) 0.52656(11) 0.0177(4) Uani 1 1 d . . . . . H2 H 0.388936 0.231296 0.514801 0.021 Uiso 1 1 calc R . . . . C3 C 0.5421(2) 0.13298(19) 0.59470(11) 0.0182(4) Uani 1 1 d . . . . . H3A H 0.497142 0.048954 0.579595 0.022 Uiso 1 1 calc R . . . . H3B H 0.499120 0.164364 0.639940 0.022 Uiso 1 1 calc R . . . . C4 C 0.7140(2) 0.11705(17) 0.62044(11) 0.0149(4) Uani 1 1 d . . . . . C5 C 0.7900(2) 0.24698(17) 0.61642(10) 0.0147(4) Uani 1 1 d . . . . . C6 C 0.9391(2) 0.26358(18) 0.65036(10) 0.0162(4) Uani 1 1 d . . . . . H6 H 0.992612 0.193832 0.676568 0.019 Uiso 1 1 calc R . . . . C7 C 1.0134(2) 0.37875(19) 0.64739(11) 0.0193(4) Uani 1 1 d . . . . . C8 C 0.9331(2) 0.47961(18) 0.60764(11) 0.0213(4) Uani 1 1 d . . . . . H8 H 0.981491 0.558929 0.604302 0.026 Uiso 1 1 calc R . . . . C9 C 0.7844(2) 0.46573(18) 0.57310(11) 0.0203(4) Uani 1 1 d . . . . . H9 H 0.731544 0.535127 0.546123 0.024 Uiso 1 1 calc R . . . . C10 C 0.7121(2) 0.35001(18) 0.57784(11) 0.0161(4) Uani 1 1 d . . . . . C11 C 0.7774(2) 0.02794(17) 0.56624(10) 0.0142(3) Uani 1 1 d . . . . . H11 H 0.764291 0.048434 0.511922 0.017 Uiso 1 1 calc R . . . . C12 C 0.8507(2) -0.07776(17) 0.59095(10) 0.0143(3) Uani 1 1 d . . . . . C13 C 0.8748(2) -0.12142(18) 0.67368(11) 0.0173(4) Uani 1 1 d . . . . . C14 C 0.8135(2) -0.03744(19) 0.72766(11) 0.0193(4) Uani 1 1 d . . . . . H14 H 0.825191 -0.060434 0.781562 0.023 Uiso 1 1 calc R . . . . C15 C 0.7419(2) 0.07015(18) 0.70398(11) 0.0175(4) Uani 1 1 d . . . . . H15 H 0.706107 0.120446 0.742399 0.021 Uiso 1 1 calc R . . . . O16 O 0.54848(16) 0.17440(12) 0.46010(9) 0.0176(3) Uani 1 1 d . . . . . C17 C 0.4950(2) 0.2420(2) 0.38798(11) 0.0210(4) Uani 1 1 d . . . . . H17A H 0.394204 0.276583 0.389834 0.025 Uiso 1 1 calc R . . . . H17B H 0.485298 0.181652 0.343429 0.025 Uiso 1 1 calc R . . . . C18 C 0.5969(3) 0.3493(2) 0.37354(13) 0.0276(5) Uani 1 1 d . . . . . H18A H 0.588131 0.418974 0.410053 0.041 Uiso 1 1 calc GR . . . . H18B H 0.567965 0.379551 0.319354 0.041 Uiso 1 1 calc GR . . . . H18C H 0.700671 0.319119 0.381835 0.041 Uiso 1 1 calc GR . . . . Br19 Br 0.93171(2) -0.18300(2) 0.51944(2) 0.01712(10) Uani 1 1 d . . . . . O20 O 0.93961(17) -0.22040(14) 0.69547(9) 0.0240(3) Uani 1 1 d . . . . . C21 C 1.1750(2) 0.3961(2) 0.68667(13) 0.0241(4) Uani 1 1 d . . . . . H21A H 1.214548 0.314299 0.709798 0.029 Uiso 1 1 calc R . . . . H21B H 1.235292 0.421011 0.646617 0.029 Uiso 1 1 calc R . . . . C22 C 1.1915(2) 0.4959(2) 0.75036(12) 0.0236(4) Uani 1 1 d . . . . . H22 H 1.148756 0.576992 0.736865 0.028 Uiso 1 1 calc R . . . . C23 C 1.2610(2) 0.4788(2) 0.82341(13) 0.0287(5) Uani 1 1 d . . . . . H23A H 1.305134 0.398923 0.839101 0.034 Uiso 1 1 calc R . . . . H23B H 1.266807 0.546249 0.860299 0.034 Uiso 1 1 calc R . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0220(7) 0.0132(6) 0.0215(7) -0.0020(5) 0.0036(5) 0.0023(5) C2 0.0161(9) 0.0160(9) 0.0219(9) -0.0008(7) 0.0059(7) 0.0005(7) C3 0.0195(9) 0.0168(9) 0.0207(9) -0.0001(7) 0.0101(7) -0.0005(7) C4 0.0200(9) 0.0114(8) 0.0148(8) -0.0003(7) 0.0072(7) -0.0012(7) C5 0.0226(9) 0.0119(8) 0.0119(8) -0.0006(6) 0.0091(7) -0.0006(7) C6 0.0231(9) 0.0134(9) 0.0134(8) -0.0010(7) 0.0069(7) 0.0002(7) C7 0.0247(10) 0.0172(9) 0.0178(9) -0.0039(7) 0.0082(7) -0.0035(8) C8 0.0316(11) 0.0135(9) 0.0196(9) -0.0014(7) 0.0070(8) -0.0063(8) C9 0.0328(11) 0.0119(9) 0.0166(9) 0.0006(7) 0.0057(8) 0.0010(8) C10 0.0215(9) 0.0144(9) 0.0136(8) -0.0015(7) 0.0062(7) -0.0003(7) C11 0.0145(8) 0.0149(9) 0.0142(8) -0.0003(7) 0.0055(6) -0.0031(7) C12 0.0171(8) 0.0131(8) 0.0140(8) -0.0026(7) 0.0069(6) -0.0017(7) C13 0.0202(9) 0.0149(9) 0.0178(9) 0.0026(7) 0.0061(7) -0.0044(7) C14 0.0277(10) 0.0188(9) 0.0126(8) 0.0037(7) 0.0067(7) -0.0044(8) C15 0.0259(10) 0.0155(9) 0.0135(8) -0.0020(7) 0.0097(7) -0.0048(7) O16 0.0209(7) 0.0156(7) 0.0164(6) -0.0010(5) 0.0033(5) 0.0013(5) C17 0.0224(10) 0.0216(10) 0.0175(9) 0.0003(7) -0.0005(7) 0.0003(8) C18 0.0339(12) 0.0281(11) 0.0202(10) 0.0049(9) 0.0030(8) -0.0065(10) Br19 0.01897(14) 0.01611(14) 0.01790(14) -0.00158(6) 0.00770(8) 0.00238(6) O20 0.0314(8) 0.0180(7) 0.0237(7) 0.0075(6) 0.0083(6) 0.0043(6) C21 0.0223(10) 0.0225(10) 0.0288(11) -0.0035(8) 0.0079(8) -0.0042(8) C22 0.0226(10) 0.0225(10) 0.0265(10) -0.0034(8) 0.0064(8) -0.0053(8) C23 0.0210(10) 0.0380(13) 0.0279(11) -0.0021(9) 0.0065(8) -0.0035(9) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 2 5 -7 0.1929 -2 -6 1 0.2119 -2 -6 -3 0.2456 2 6 4 0.3657 -2 -6 6 0.2624 5 -3 -4 0.2004 -5 3 1 0.1839 2 -2 -11 0.3654 4 -2 6 0.3092 0 0 11 0.2544 5 2 -6 0.2322 1 1 10 0.2660 -5 -2 -1 0.2427 -3 -2 -8 0.3183 5 2 3 0.3057 -3 5 -4 0.1418 3 -6 0 0.2278 3 -6 -4 0.2530 6 -2 -3 0.1796 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C10 O1 C2 115.43(14) . . ? O1 C2 H2 108.2 . . ? O1 C2 C3 111.08(15) . . ? C3 C2 H2 108.2 . . ? O16 C2 O1 111.39(15) . . ? O16 C2 H2 108.2 . . ? O16 C2 C3 109.52(15) . . ? C2 C3 H3A 109.0 . . ? C2 C3 H3B 109.0 . . ? C2 C3 C4 113.04(15) . . ? H3A C3 H3B 107.8 . . ? C4 C3 H3A 109.0 . . ? C4 C3 H3B 109.0 . . ? C5 C4 C3 109.02(15) . . ? C11 C4 C3 111.26(15) . . ? C11 C4 C5 107.58(14) . . ? C15 C4 C3 107.51(15) . . ? C15 C4 C5 109.53(15) . . ? C15 C4 C11 111.91(15) . . ? C6 C5 C4 120.26(17) . . ? C6 C5 C10 118.47(17) . . ? C10 C5 C4 121.26(17) . . ? C5 C6 H6 118.8 . . ? C5 C6 C7 122.40(18) . . ? C7 C6 H6 118.8 . . ? C6 C7 C8 117.84(18) . . ? C6 C7 C21 121.65(18) . . ? C8 C7 C21 120.50(18) . . ? C7 C8 H8 119.5 . . ? C9 C8 C7 121.02(18) . . ? C9 C8 H8 119.5 . . ? C8 C9 H9 120.0 . . ? C8 C9 C10 120.03(18) . . ? C10 C9 H9 120.0 . . ? O1 C10 C5 123.77(17) . . ? O1 C10 C9 115.94(17) . . ? C9 C10 C5 120.23(18) . . ? C4 C11 H11 118.5 . . ? C12 C11 C4 123.07(16) . . ? C12 C11 H11 118.5 . . ? C11 C12 C13 123.45(17) . . ? C11 C12 Br19 120.57(14) . . ? C13 C12 Br19 115.98(13) . . ? C14 C13 C12 114.79(16) . . ? O20 C13 C12 122.90(18) . . ? O20 C13 C14 122.31(17) . . ? C13 C14 H14 118.8 . . ? C15 C14 C13 122.46(17) . . ? C15 C14 H14 118.8 . . ? C4 C15 H15 117.8 . . ? C14 C15 C4 124.31(17) . . ? C14 C15 H15 117.8 . . ? C2 O16 C17 114.87(15) . . ? O16 C17 H17A 109.0 . . ? O16 C17 H17B 109.0 . . ? O16 C17 C18 112.97(16) . . ? H17A C17 H17B 107.8 . . ? C18 C17 H17A 109.0 . . ? C18 C17 H17B 109.0 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18B 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C7 C21 H21A 109.2 . . ? C7 C21 H21B 109.2 . . ? H21A C21 H21B 107.9 . . ? C22 C21 C7 111.99(17) . . ? C22 C21 H21A 109.2 . . ? C22 C21 H21B 109.2 . . ? C21 C22 H22 117.6 . . ? C23 C22 C21 124.8(2) . . ? C23 C22 H22 117.6 . . ? C22 C23 H23A 120.0 . . ? C22 C23 H23B 120.0 . . ? H23A C23 H23B 120.0 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.431(2) . ? O1 C10 1.376(2) . ? C2 H2 1.0000 . ? C2 C3 1.512(3) . ? C2 O16 1.398(2) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C3 C4 1.553(3) . ? C4 C5 1.539(3) . ? C4 C11 1.510(2) . ? C4 C15 1.504(2) . ? C5 C6 1.388(3) . ? C5 C10 1.398(3) . ? C6 H6 0.9500 . ? C6 C7 1.392(3) . ? C7 C8 1.398(3) . ? C7 C21 1.514(3) . ? C8 H8 0.9500 . ? C8 C9 1.383(3) . ? C9 H9 0.9500 . ? C9 C10 1.393(3) . ? C11 H11 0.9500 . ? C11 C12 1.328(3) . ? C12 C13 1.481(3) . ? C12 Br19 1.9014(18) . ? C13 C14 1.464(3) . ? C13 O20 1.223(2) . ? C14 H14 0.9500 . ? C14 C15 1.334(3) . ? C15 H15 0.9500 . ? O16 C17 1.443(2) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C17 C18 1.508(3) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C21 C22 1.510(3) . ? C22 H22 0.9500 . ? C22 C23 1.320(3) . ? C23 H23A 0.9500 . ? C23 H23B 0.9500 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C2 C3 C4 -59.2(2) . . . . ? O1 C2 O16 C17 -66.1(2) . . . . ? C2 O1 C10 C5 -23.2(2) . . . . ? C2 O1 C10 C9 159.65(16) . . . . ? C2 C3 C4 C5 39.4(2) . . . . ? C2 C3 C4 C11 -79.11(19) . . . . ? C2 C3 C4 C15 158.04(16) . . . . ? C2 O16 C17 C18 88.7(2) . . . . ? C3 C2 O16 C17 170.65(15) . . . . ? C3 C4 C5 C6 167.76(16) . . . . ? C3 C4 C5 C10 -13.2(2) . . . . ? C3 C4 C11 C12 -121.25(19) . . . . ? C3 C4 C15 C14 122.2(2) . . . . ? C4 C5 C6 C7 179.15(16) . . . . ? C4 C5 C10 O1 4.8(3) . . . . ? C4 C5 C10 C9 -178.22(16) . . . . ? C4 C11 C12 C13 1.6(3) . . . . ? C4 C11 C12 Br19 -178.41(13) . . . . ? C5 C4 C11 C12 119.41(19) . . . . ? C5 C4 C15 C14 -119.4(2) . . . . ? C5 C6 C7 C8 -0.8(3) . . . . ? C5 C6 C7 C21 178.32(17) . . . . ? C6 C5 C10 O1 -176.21(16) . . . . ? C6 C5 C10 C9 0.8(3) . . . . ? C6 C7 C8 C9 0.7(3) . . . . ? C6 C7 C21 C22 -117.9(2) . . . . ? C7 C8 C9 C10 0.2(3) . . . . ? C7 C21 C22 C23 127.1(2) . . . . ? C8 C7 C21 C22 61.2(2) . . . . ? C8 C9 C10 O1 176.26(17) . . . . ? C8 C9 C10 C5 -1.0(3) . . . . ? C10 O1 C2 C3 49.5(2) . . . . ? C10 O1 C2 O16 -72.86(19) . . . . ? C10 C5 C6 C7 0.1(3) . . . . ? C11 C4 C5 C6 -71.5(2) . . . . ? C11 C4 C5 C10 107.55(19) . . . . ? C11 C4 C15 C14 -0.2(3) . . . . ? C11 C12 C13 C14 -1.0(3) . . . . ? C11 C12 C13 O20 178.32(19) . . . . ? C12 C13 C14 C15 -0.2(3) . . . . ? C13 C14 C15 C4 0.7(3) . . . . ? C15 C4 C5 C6 50.4(2) . . . . ? C15 C4 C5 C10 -130.60(18) . . . . ? C15 C4 C11 C12 -1.0(3) . . . . ? O16 C2 C3 C4 64.2(2) . . . . ? Br19 C12 C13 C14 179.00(13) . . . . ? Br19 C12 C13 O20 -1.6(3) . . . . ? O20 C13 C14 C15 -179.52(19) . . . . ? C21 C7 C8 C9 -178.50(18) . . . . ? loop_ _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z 1.9946 4.9922 -6.9972 -0.7868 -0.3201 0.5049 -1.9973 -5.9923 0.9995 0.8850 0.3148 0.0490 -1.9990 -5.9933 -2.9990 0.8534 0.3140 0.4097 1.9995 5.9936 3.9986 -0.8456 -0.3138 -0.4998 -1.9952 -5.9910 5.9975 0.9244 0.3158 -0.4019 4.9897 -2.9935 -3.9990 0.3933 -0.8605 0.2424 -4.9910 2.9928 1.0002 -0.4170 0.8599 0.0281 1.9917 -1.9987 -10.9960 0.1996 -0.3493 0.9548 3.9958 -1.9930 5.9972 0.3290 -0.6850 -0.6408 0.0047 0.0029 10.9957 0.0867 0.0022 -0.9920 4.9897 1.9987 -5.9980 -0.3495 -0.8406 0.3590 1.0028 1.0018 9.9961 -0.0689 -0.1635 -0.9458 -4.9927 -2.0005 -0.9993 0.2944 0.8392 0.2722 -2.9989 -2.0011 -7.9967 0.2346 0.4988 0.8409 4.9936 2.0010 2.9985 -0.2786 -0.8388 -0.4526 -2.9961 4.9898 -3.9980 -0.7518 0.5281 0.3909 2.9942 -5.9894 -0.0005 0.8657 -0.5329 -0.0174 2.9925 -5.9905 -3.9990 0.8342 -0.5337 0.3433 5.9887 -1.9941 -2.9994 0.2535 -1.0258 0.1082