#------------------------------------------------------------------------------ #$Date: 2024-11-21 01:07:56 +0200 (Thu, 21 Nov 2024) $ #$Revision: 296017 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/32/1573214.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_1573214 loop_ _publ_author_name 'Xu, Zurong' 'Zhu, Dong' 'Wu, Rui' 'Zhu, Shifa' _publ_section_title ; Tandem Rh(II)-catalyzed 1,3-acyloxy migration/intermolecular [2+2] cycloaddition of electronically deficient propargylic esters with alkenes and alkynes ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D4SC06458E _journal_year 2024 _chemical_formula_moiety 'C14 H13 Br O3' _chemical_formula_sum 'C14 H13 Br O3' _chemical_formula_weight 309.15 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_date 2023-04-01 _audit_creation_method ; Olex2 1.5-beta (compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439) ; _audit_update_record ; 2024-02-27 deposited with the CCDC. 2024-11-18 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 96.115(9) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 6.5459(6) _cell_length_b 7.4134(4) _cell_length_c 27.118(3) _cell_measurement_reflns_used 2753 _cell_measurement_temperature 149.99(10) _cell_measurement_theta_max 70.9200 _cell_measurement_theta_min 3.2270 _cell_volume 1308.5(2) _computing_cell_refinement 'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)' _computing_molecular_graphics 'Olex2 1.5-beta (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5-beta (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXS (Sheldrick, 2008)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 149.99(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 5.2684 _diffrn_detector_type AtlasS2 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _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 -117.00 -8.00 1.00 1.00 -- -40.92 -77.00 0.00 109 2 \w -115.00 -17.00 1.00 1.00 -- -40.92 -37.00-150.00 98 3 \w 23.00 97.00 1.00 1.00 -- 40.92-125.00 30.00 74 4 \w 17.00 92.00 1.00 1.00 -- 40.92-117.00-150.00 75 5 \w 17.00 115.00 1.00 1.00 -- 40.92 37.00 120.00 98 6 \w 81.00 178.00 1.00 1.50 -- 106.95 45.00 -90.00 97 7 \w 34.00 121.00 1.00 1.50 -- 106.95-125.00 150.00 87 8 \w 32.00 74.00 1.00 1.50 -- 106.95 -15.00-150.00 42 9 \w 42.00 86.00 1.00 1.50 -- 106.95 -30.00 -60.00 44 10 \w 100.00 135.00 1.00 1.50 -- 106.95 -30.00 120.00 35 11 \w 106.00 134.00 1.00 1.50 -- 106.95 -30.00 -60.00 28 12 \w 126.00 178.00 1.00 1.50 -- 106.95 125.00 30.00 52 13 \w 32.00 95.00 1.00 1.50 -- 106.95 -30.00 120.00 63 14 \w 81.00 149.00 1.00 1.50 -- 106.95 45.00 120.00 68 15 \w 87.00 144.00 1.00 1.50 -- 106.95 -15.00-150.00 57 16 \w 35.00 136.00 1.00 1.50 -- 106.95 -61.00 120.00 101 17 \w 82.00 109.00 1.00 1.50 -- 106.95 -94.00 -60.00 27 18 \w 32.00 140.00 1.00 1.50 -- 106.95 -77.00 -60.00 108 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, AtlasS2' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0742923000 _diffrn_orient_matrix_UB_12 0.0579478000 _diffrn_orient_matrix_UB_13 0.0535210000 _diffrn_orient_matrix_UB_21 0.0124809000 _diffrn_orient_matrix_UB_22 0.1972671000 _diffrn_orient_matrix_UB_23 -0.0172792000 _diffrn_orient_matrix_UB_31 -0.2242336000 _diffrn_orient_matrix_UB_32 0.0301412000 _diffrn_orient_matrix_UB_33 0.0102624000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_unetI/netI 0.1447 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_limit_l_min -3 _diffrn_reflns_number 2308 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 66.568 _diffrn_reflns_theta_max 66.568 _diffrn_reflns_theta_min 3.278 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 4.273 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.48611 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'light colourless' _exptl_crystal_density_diffrn 1.569 _exptl_crystal_description prism _exptl_crystal_F_000 624 _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _refine_diff_density_max 3.426 _refine_diff_density_min -1.543 _refine_diff_density_rms 0.439 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 2.595 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 165 _refine_ls_number_reflns 2308 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 2.595 _refine_ls_R_factor_all 0.1251 _refine_ls_R_factor_gt 0.1137 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.3452 _refine_ls_wR_factor_ref 0.3523 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1980 _reflns_number_total 2308 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4sc06458e2.cif _cod_data_source_block 2_211_1 _cod_original_cell_volume 1308.48(19) _cod_database_code 1573214 _shelx_shelxl_version_number 2018/3 _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. ; _shelx_estimated_absorpt_t_max 0.726 _shelx_estimated_absorpt_t_min 0.607 _olex2_refinement_description ; 1. Twinned data refinement Scales: 0.712(7) 0.288(7) 2. 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 3.a Ternary CH refined with riding coordinates: C7(H7) 3.b Secondary CH2 refined with riding coordinates: C8(H8A,H8B), C10(H10A,H10B) 3.c Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3), C5(H5), C6(H6), C11(H11) 3.d Idealised Me refined as rotating group: C14(H14A,H14B,H14C) ; _shelx_res_file ; TITL x2r=2-211-1_a.res in P2(1)/c 2_211_1.res created by SHELXL-2018/3 at 15:55:55 on 01-Apr-2023 REM Old TITL X2R=2-211-1 in P2(1) REM SHELXT solution in P2(1)/c: R1 0.294, Rweak 0.436, Alpha 0.220 REM 3.179 for 212 systematic absences, Orientation as input REM Formula found by SHELXT: C10 N4 O3 Br CELL 1.54184 6.5459 7.4134 27.118 90 96.115 90 ZERR 4 0.0006 0.0004 0.0025 0 0.009 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H Br O UNIT 56 52 4 12 L.S. 20 PLAN 2 SIZE 0.08 0.12 0.13 TEMP -120 CONF BOND LIST 4 MORE -1 BOND $H fmap 2 53 acta MERG 0 SHEL 999 0.84 REM REM REM WGHT 0.200000 BASF 0.28775 FVAR 10.73359 PART 1 BR1 3 0.843492 0.198992 0.546346 11.00000 0.07419 0.05171 = 0.05502 0.00701 -0.00921 0.00343 PART 0 O1 4 0.185955 0.507475 0.203203 11.00000 0.05573 0.03750 = 0.03439 -0.00572 0.00892 -0.00168 O2 4 0.176914 0.226945 0.172629 11.00000 0.07622 0.06190 = 0.05252 -0.00343 0.02965 0.00056 O3 4 -0.238344 0.428952 0.192862 11.00000 0.05176 0.06013 = 0.04765 0.00980 0.00321 0.00153 C1 1 0.439896 0.401641 0.404889 11.00000 0.04312 0.04239 = 0.04196 0.00396 0.01620 -0.00164 C2 1 0.650822 0.452637 0.413777 11.00000 0.03974 0.05043 = 0.05149 0.00788 0.02142 -0.00339 AFIX 43 H2 2 0.710064 0.527383 0.390652 11.00000 -1.20000 AFIX 0 C3 1 0.766178 0.395054 0.454881 11.00000 0.04418 0.04623 = 0.04101 -0.00855 0.00134 0.00009 AFIX 43 H3 2 0.906332 0.429443 0.461187 11.00000 -1.20000 AFIX 0 C4 1 0.675358 0.283219 0.488242 11.00000 0.05056 0.04202 = 0.03852 -0.00069 0.01628 0.01174 C5 1 0.475997 0.237091 0.481007 11.00000 0.05134 0.02559 = 0.04235 0.00324 0.01947 -0.00031 AFIX 43 H5 2 0.418572 0.165640 0.505138 11.00000 -1.20000 AFIX 0 C6 1 0.354192 0.291106 0.439538 11.00000 0.06252 0.04863 = 0.04064 -0.00152 0.00324 -0.00044 AFIX 43 H6 2 0.214420 0.254737 0.434214 11.00000 -1.20000 AFIX 0 C7 1 0.314123 0.474981 0.360412 11.00000 0.08258 0.01497 = 0.04701 -0.00502 -0.00630 -0.00092 AFIX 13 H7 2 0.274446 0.603039 0.365994 11.00000 -1.20000 AFIX 0 C8 1 0.398611 0.452973 0.308076 11.00000 0.05096 0.04410 = 0.04963 -0.00060 0.01804 -0.00384 AFIX 23 H8A 2 0.456620 0.565144 0.295475 11.00000 -1.20000 H8B 2 0.494319 0.350349 0.306292 11.00000 -1.20000 AFIX 0 C9 1 0.188660 0.414830 0.286801 11.00000 0.04823 0.03934 = 0.03888 -0.00187 0.00895 0.00397 C10 1 0.126620 0.365192 0.336052 11.00000 0.04331 0.04279 = 0.05332 -0.00299 -0.00117 -0.00063 AFIX 23 H10A 2 0.134756 0.234275 0.343194 11.00000 -1.20000 H10B 2 -0.008157 0.414943 0.342655 11.00000 -1.20000 AFIX 0 C11 1 -0.133978 0.408877 0.234022 11.00000 0.03908 0.03148 = 0.05461 0.00204 0.02209 0.00258 AFIX 43 H11 2 -0.203426 0.373370 0.261480 11.00000 -1.20000 AFIX 0 C12 1 0.076883 0.435397 0.241894 11.00000 0.03999 0.04502 = 0.04190 -0.00475 0.01421 0.00518 C13 1 0.215677 0.381794 0.168109 11.00000 0.04161 0.03187 = 0.04677 -0.00114 -0.00077 -0.01253 C14 1 0.311841 0.467653 0.125298 11.00000 0.04718 0.04422 = 0.04271 0.00191 0.01615 -0.00353 AFIX 137 H14A 2 0.254609 0.588686 0.119082 11.00000 -1.50000 H14B 2 0.282101 0.393454 0.095488 11.00000 -1.50000 H14C 2 0.460887 0.476241 0.133687 11.00000 -1.50000 AFIX 0 HKLF 5 REM x2r=2-211-1_a.res in P2(1)/c REM wR2 = 0.3523, GooF = S = 2.595, Restrained GooF = 2.595 for all data REM R1 = 0.1137 for 1980 Fo > 4sig(Fo) and 0.1251 for all 2308 data REM 165 parameters refined using 0 restraints END WGHT 0.2000 0.0000 REM Highest difference peak 3.426, deepest hole -1.543, 1-sigma level 0.439 Q1 1 0.9882 0.1994 0.5440 11.00000 0.05 3.43 Q2 1 0.8494 0.2940 0.5455 11.00000 0.05 2.00 ; _shelx_res_checksum 2077 _shelx_hkl_file ; 1 0 0 160024 5783 1 2 0 0 2348415 1364641 1 3 0 0 1394040 21195 1 4 0 0 149964 12433 1 -5 0 4 54775 3919 -2 5 0 0 54775 3919 1 6 0 0 50904 3441 1 7 0 0 13110 3879 1 1 1 0 1267509 421106 1 2 1 0 375603 169693 1 3 1 0 7089 3011 1 4 1 0 30888 3998 1 -5 -1 4 66762 2740 -2 5 1 0 66762 2740 1 6 1 0 5878 1179 1 7 1 0 18797 2716 1 0 -2 0 40135 1864 -2 0 2 0 40135 1864 1 1 2 0 390027 108538 1 2 2 0 193978 82867 1 3 2 0 228705 114496 1 4 2 0 35962 1920 1 -5 -2 4 6229 1856 -2 5 2 0 6229 1856 1 6 2 0 30976 2636 1 7 2 0 7336 1418 1 1 3 0 38295 4875 1 2 3 0 90131 14703 1 3 3 0 124635 51740 1 4 3 0 6165 8140 1 -5 -3 4 15683 1975 -2 5 3 0 15683 1975 1 6 3 0 4954 1155 1 7 3 0 1561 812 1 0 -4 0 184811 6356 -2 0 4 0 184811 6356 1 1 4 0 182063 53254 1 2 4 0 5783 1935 1 3 4 0 62413 38072 1 4 4 0 40924 14050 1 -5 -4 4 6683 1155 -2 5 4 0 6683 1155 1 6 4 0 21983 2047 1 7 4 0 279 1187 1 1 5 0 26029 3943 1 2 5 0 4341 725 1 3 5 0 81402 36049 1 4 5 0 12999 1235 1 -5 -5 4 438 645 -2 5 5 0 438 645 1 6 5 0 9741 1689 1 0 -6 0 18996 1426 -2 0 6 0 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2 1 35595 2421 1 6 2 1 4253 1155 1 7 2 1 924 804 1 -7 3 1 231 693 1 -6 3 1 12513 1704 1 5 -3 -3 17013 4078 -2 -5 3 1 17013 4078 1 -4 3 1 21282 15046 1 -3 3 1 118263 22835 1 -2 3 1 81258 1848 1 -1 3 1 38295 4875 1 0 -3 1 297849 5058 -2 0 3 1 297849 5058 1 1 3 1 450983 99387 1 2 3 1 120438 60653 1 3 3 1 108459 33572 1 4 3 1 62254 3138 1 5 3 1 7344 1466 1 6 3 1 14098 2254 1 7 3 1 15149 2828 1 -7 4 1 4373 916 1 -6 4 1 1832 701 1 5 -4 -3 37531 23441 -2 -5 4 1 37531 23441 1 -4 4 1 117132 50777 1 -3 4 1 263 581 1 -2 4 1 474519 14560 1 -1 4 1 182063 53254 1 0 -4 1 204189 4707 -2 0 4 1 204189 4707 1 1 4 1 147001 32258 1 2 4 1 86372 23019 1 3 4 1 10625 2549 1 4 4 1 22581 2198 1 5 4 1 52075 3027 1 6 4 1 6364 1489 1 7 4 1 -80 1107 1 -6 5 1 4699 749 1 5 -5 -3 12258 5671 -2 -5 5 1 12258 5671 1 -4 5 1 11677 6221 1 -3 5 1 217005 89104 1 -2 5 1 58949 2342 1 -1 5 1 26029 3943 1 0 -5 1 353811 7320 -2 0 5 1 353811 7320 1 1 5 1 80510 8084 1 2 5 1 150625 35516 1 3 5 1 116153 46006 1 4 5 1 23282 6659 1 5 5 1 14974 1760 1 6 5 1 4301 1115 1 -6 6 1 48 1426 1 5 -6 -3 12346 2875 -2 -5 6 1 12346 2875 1 -4 6 1 35524 4628 1 -3 6 1 6372 789 1 -2 6 1 100653 3927 1 -1 6 1 42620 3202 1 0 -6 1 15468 948 -2 0 6 1 15468 948 1 1 6 1 80127 9590 1 2 6 1 55699 9845 1 3 6 1 4030 677 1 4 6 1 25464 9534 1 5 6 1 4811 948 1 6 6 1 -828 828 1 5 -7 -3 6404 852 -2 -5 7 1 6404 852 1 -4 7 1 1864 1474 1 -3 7 1 8475 3043 1 -2 7 1 15540 1027 1 -1 7 1 12170 1179 1 0 -7 1 17563 1115 -2 0 7 1 17563 1115 1 1 7 1 62334 5950 1 2 7 1 17308 1935 1 3 7 1 51581 2278 1 4 7 1 8427 940 1 5 7 1 2955 542 1 -4 8 1 1203 454 1 -3 8 1 2166 621 1 -2 8 1 4723 765 1 -1 8 1 9494 916 1 0 -8 1 1593 486 -2 0 8 1 1593 486 1 1 8 1 2190 486 1 2 8 1 6149 701 1 3 8 1 13684 1235 1 -1 9 1 9343 1083 1 0 -9 1 -112 470 -2 0 9 1 -112 470 1 1 9 1 8443 1314 1 -7 0 2 12999 4166 1 -6 0 2 39323 27710 1 5 0 -2 5687 1346 -2 -5 0 2 5687 1346 1 -4 0 2 406 526 1 -3 0 2 139992 7543 1 -2 0 2 2348415 1364641 1 0 0 2 151135 4349 -2 0 0 2 151135 4349 1 1 0 2 725 239 1 2 0 2 84588 2923 1 3 0 2 46420 5631 1 4 0 2 131788 11924 1 5 0 2 73349 5663 1 6 0 2 3911 940 1 7 0 2 27583 4484 1 -7 1 2 30609 7184 1 -6 1 2 6189 2708 1 5 -1 -2 35635 21593 -2 -5 1 2 35635 21593 1 -4 1 2 65209 2684 1 -3 1 2 121370 78391 1 -2 1 2 375603 169693 1 -1 1 2 6424665 3201556 1 0 -1 2 233006 7877 -2 0 1 2 233006 7877 1 1 1 2 198813 18128 1 2 1 2 2496866 25193 1 3 1 2 162477 4938 1 4 1 2 15731 2636 1 5 1 2 102230 3473 1 6 1 2 21290 9024 1 7 1 2 5321 9040 1 -7 2 2 669 685 1 -6 2 2 18343 4357 1 5 -2 -2 31191 16639 -2 -5 2 2 31191 16639 1 -4 2 2 71589 3250 1 -3 2 2 218192 98558 1 -2 2 2 193978 82867 1 -1 2 2 21059 948 1 0 -2 2 9887742 56591 -2 0 2 2 9887742 56591 1 1 2 2 351549 77021 1 2 2 2 31087 5058 1 3 2 2 131501 4978 1 4 2 2 65416 4914 1 5 2 2 22597 2015 1 6 2 2 10514 2063 1 7 2 2 5169 1203 1 -7 3 2 6093 1243 1 -6 3 2 15866 5464 1 5 -3 -2 17101 3274 -2 -5 3 2 17101 3274 1 -4 3 2 78256 2501 1 -3 3 2 118263 22835 1 -2 3 2 90131 14703 1 -1 3 2 450983 99387 1 0 -3 2 366642 5695 -2 0 3 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31 14982 1800 1 0 3 31 18996 1625 1 -1 0 32 14456 2971 1 0 0 32 59259 6037 1 1 0 32 8594 2143 1 -2 1 32 5010 1426 1 -1 1 32 12792 1537 1 0 1 32 1298 605 1 1 1 32 16081 1943 1 -2 2 32 1704 916 1 -1 2 32 2015 677 1 0 2 32 20143 1697 1 1 2 32 2716 1243 1 -2 1 33 -382 573 1 -1 1 33 6961 1330 1 0 1 33 2605 693 1 ; _shelx_hkl_checksum 17862 _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 1.662 _oxdiff_exptl_absorpt_empirical_full_min 0.683 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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 Br1 Br 0.8435(2) 0.19899(15) 0.54635(4) 0.0615(4) Uani 1 1 d . . . A 1 O1 O 0.1860(11) 0.5075(8) 0.2032(2) 0.0422(16) Uani 1 1 d . . . . . O2 O 0.1769(15) 0.2269(11) 0.1726(3) 0.062(2) Uani 1 1 d . . . . . O3 O -0.2383(12) 0.4290(10) 0.1929(3) 0.053(2) Uani 1 1 d . . . . . C1 C 0.4399(15) 0.4016(12) 0.4049(3) 0.042(2) Uani 1 1 d . . . . . C2 C 0.6508(15) 0.4526(14) 0.4138(4) 0.046(2) Uani 1 1 d . . . . . H2 H 0.710064 0.527383 0.390652 0.055 Uiso 1 1 calc R U . . . C3 C 0.7662(16) 0.3951(12) 0.4549(3) 0.044(2) Uani 1 1 d . . . . . H3 H 0.906332 0.429443 0.461187 0.053 Uiso 1 1 calc R U . . . C4 C 0.6754(16) 0.2832(11) 0.4882(4) 0.043(2) Uani 1 1 d . . . . . C5 C 0.4760(15) 0.2371(11) 0.4810(3) 0.039(2) Uani 1 1 d . . . . . H5 H 0.418572 0.165640 0.505138 0.046 Uiso 1 1 calc R U . . . C6 C 0.354(2) 0.2911(13) 0.4395(4) 0.051(3) Uani 1 1 d . . . . . H6 H 0.214420 0.254737 0.434214 0.061 Uiso 1 1 calc R U . . . C7 C 0.3141(19) 0.4750(10) 0.3604(3) 0.049(3) Uani 1 1 d . . . . . H7 H 0.274446 0.603039 0.365994 0.059 Uiso 1 1 calc R U . . . C8 C 0.3986(17) 0.4530(14) 0.3081(4) 0.047(3) Uani 1 1 d . . . . . H8A H 0.456620 0.565144 0.295475 0.057 Uiso 1 1 calc R U . . . H8B H 0.494319 0.350349 0.306292 0.057 Uiso 1 1 calc R U . . . C9 C 0.1887(16) 0.4148(11) 0.2868(3) 0.042(2) Uani 1 1 d . . . . . C10 C 0.1266(16) 0.3652(13) 0.3361(4) 0.047(2) Uani 1 1 d . . . . . H10A H 0.134756 0.234275 0.343194 0.056 Uiso 1 1 calc R U . . . H10B H -0.008157 0.414943 0.342655 0.056 Uiso 1 1 calc R U . . . C11 C -0.1340(15) 0.4089(11) 0.2340(4) 0.040(2) Uani 1 1 d . . . . . H11 H -0.203426 0.373370 0.261480 0.049 Uiso 1 1 calc R U . . . C12 C 0.0769(15) 0.4354(13) 0.2419(3) 0.042(2) Uani 1 1 d . . . . . C13 C 0.2157(15) 0.3818(11) 0.1681(3) 0.040(2) Uani 1 1 d . . . . . C14 C 0.3118(15) 0.4677(13) 0.1253(3) 0.044(2) Uani 1 1 d . . . . . H14A H 0.254609 0.588686 0.119082 0.066 Uiso 1 1 calc R U . . . H14B H 0.282101 0.393454 0.095488 0.066 Uiso 1 1 calc R U . . . H14C H 0.460887 0.476241 0.133687 0.066 Uiso 1 1 calc R U . . . 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 Br1 0.0742(8) 0.0517(6) 0.0550(7) 0.0070(4) -0.0092(6) 0.0034(5) O1 0.056(4) 0.038(3) 0.034(3) -0.006(2) 0.009(3) -0.002(3) O2 0.076(5) 0.062(4) 0.053(4) -0.003(3) 0.030(4) 0.001(4) O3 0.052(4) 0.060(4) 0.048(4) 0.010(3) 0.003(3) 0.002(3) C1 0.043(5) 0.042(4) 0.042(4) 0.004(4) 0.016(4) -0.002(4) C2 0.040(5) 0.050(4) 0.051(5) 0.008(4) 0.021(4) -0.003(4) C3 0.044(5) 0.046(4) 0.041(4) -0.009(4) 0.001(4) 0.000(4) C4 0.051(5) 0.042(4) 0.039(4) -0.001(4) 0.016(4) 0.012(4) C5 0.051(5) 0.026(3) 0.042(4) 0.003(3) 0.019(4) 0.000(3) C6 0.063(6) 0.049(5) 0.041(5) -0.002(4) 0.003(5) 0.000(4) C7 0.083(7) 0.015(3) 0.047(5) -0.005(3) -0.006(5) -0.001(4) C8 0.051(5) 0.044(4) 0.050(5) -0.001(4) 0.018(4) -0.004(4) C9 0.048(5) 0.039(4) 0.039(4) -0.002(3) 0.009(4) 0.004(4) C10 0.043(5) 0.043(4) 0.053(5) -0.003(4) -0.001(4) -0.001(4) C11 0.039(4) 0.031(3) 0.055(5) 0.002(3) 0.022(4) 0.003(3) C12 0.040(4) 0.045(4) 0.042(4) -0.005(4) 0.014(4) 0.005(4) C13 0.042(5) 0.032(4) 0.047(5) -0.001(3) -0.001(4) -0.013(3) C14 0.047(5) 0.044(4) 0.043(4) 0.002(4) 0.016(4) -0.004(4) 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_ _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 C13 O1 C12 112.1(7) . . ? C2 C1 C7 118.8(9) . . ? C6 C1 C2 119.3(9) . . ? C6 C1 C7 121.9(10) . . ? C1 C2 H2 119.9 . . ? C3 C2 C1 120.2(9) . . ? C3 C2 H2 119.9 . . ? C2 C3 H3 120.6 . . ? C2 C3 C4 118.8(10) . . ? C4 C3 H3 120.6 . . ? C3 C4 Br1 118.3(8) . . ? C5 C4 Br1 119.9(7) . . ? C5 C4 C3 121.8(9) . . ? C4 C5 H5 119.4 . . ? C4 C5 C6 121.2(10) . . ? C6 C5 H5 119.4 . . ? C1 C6 H6 120.6 . . ? C5 C6 C1 118.7(11) . . ? C5 C6 H6 120.6 . . ? C1 C7 H7 110.7 . . ? C1 C7 C8 118.2(9) . . ? C1 C7 C10 119.7(8) . . ? C8 C7 H7 110.7 . . ? C10 C7 H7 110.7 . . ? C10 C7 C8 84.3(7) . . ? C7 C8 H8A 113.9 . . ? C7 C8 H8B 113.9 . . ? H8A C8 H8B 111.1 . . ? C9 C8 C7 88.3(8) . . ? C9 C8 H8A 113.9 . . ? C9 C8 H8B 113.9 . . ? C8 C9 C10 91.6(8) . . ? C12 C9 C8 136.5(10) . . ? C12 C9 C10 131.4(10) . . ? C7 C10 H10A 113.9 . . ? C7 C10 H10B 113.9 . . ? C9 C10 C7 88.5(8) . . ? C9 C10 H10A 113.9 . . ? C9 C10 H10B 113.9 . . ? H10A C10 H10B 111.1 . . ? O3 C11 H11 118.0 . . ? O3 C11 C12 124.0(9) . . ? C12 C11 H11 118.0 . . ? C9 C12 O1 115.8(9) . . ? C9 C12 C11 123.6(9) . . ? C11 C12 O1 120.3(8) . . ? O1 C13 C14 110.5(7) . . ? O2 C13 O1 122.9(9) . . ? O2 C13 C14 126.6(9) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14B 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? 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 Br1 C4 1.927(10) . ? O1 C12 1.434(12) . ? O1 C13 1.361(11) . ? O2 C13 1.185(12) . ? O3 C11 1.254(12) . ? C1 C2 1.427(14) . ? C1 C6 1.408(15) . ? C1 C7 1.489(13) . ? C2 H2 0.9500 . ? C2 C3 1.347(13) . ? C3 H3 0.9500 . ? C3 C4 1.405(14) . ? C4 C5 1.343(15) . ? C5 H5 0.9500 . ? C5 C6 1.367(14) . ? C6 H6 0.9500 . ? C7 H7 1.0000 . ? C7 C8 1.586(14) . ? C7 C10 1.560(14) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C8 C9 1.460(14) . ? C9 C10 1.483(14) . ? C9 C12 1.361(13) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11 0.9500 . ? C11 C12 1.388(14) . ? C13 C14 1.518(13) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? 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 Br1 C4 C5 C6 -178.4(7) . . . . ? O3 C11 C12 O1 6.7(14) . . . . ? O3 C11 C12 C9 179.4(9) . . . . ? C1 C2 C3 C4 0.6(15) . . . . ? C1 C7 C8 C9 140.4(8) . . . . ? C1 C7 C10 C9 -138.7(9) . . . . ? C2 C1 C6 C5 0.5(14) . . . . ? C2 C1 C7 C8 52.3(11) . . . . ? C2 C1 C7 C10 152.4(10) . . . . ? C2 C3 C4 Br1 179.1(7) . . . . ? C2 C3 C4 C5 -2.1(14) . . . . ? C3 C4 C5 C6 2.8(14) . . . . ? C4 C5 C6 C1 -2.0(15) . . . . ? C6 C1 C2 C3 0.1(15) . . . . ? C6 C1 C7 C8 -130.9(10) . . . . ? C6 C1 C7 C10 -30.8(14) . . . . ? C7 C1 C2 C3 177.0(9) . . . . ? C7 C1 C6 C5 -176.3(9) . . . . ? C7 C8 C9 C10 -20.7(7) . . . . ? C7 C8 C9 C12 151.7(11) . . . . ? C8 C7 C10 C9 -19.4(7) . . . . ? C8 C9 C10 C7 21.0(7) . . . . ? C8 C9 C12 O1 2.5(16) . . . . ? C8 C9 C12 C11 -170.5(10) . . . . ? C10 C7 C8 C9 19.7(7) . . . . ? C10 C9 C12 O1 172.3(9) . . . . ? C10 C9 C12 C11 -0.7(16) . . . . ? C12 O1 C13 O2 -8.4(13) . . . . ? C12 O1 C13 C14 174.2(7) . . . . ? C12 C9 C10 C7 -152.0(10) . . . . ? C13 O1 C12 C9 109.8(9) . . . . ? C13 O1 C12 C11 -77.0(10) . . . . ? loop_ _twin_individual_id _twin_individual_mass_fraction_refined 1 0.712(7) 2 0.288(7)