#------------------------------------------------------------------------------ #$Date: 2020-05-27 06:35:33 +0300 (Wed, 27 May 2020) $ #$Revision: 252369 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/75/7157516.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_7157516 loop_ _publ_author_name 'Luo, Si-qin' 'Liu, Wei' 'Ruan, Banfeng' 'Fan, Shilu' 'Zhu, Huixia' 'Tao, Wei' 'Xiao, Hua' _publ_section_title ; P(NMe2)3 mediated cyclopropanation of \a-methylene-\b-lactams for rapid syntheses of spirocyclopropyl \b-lactams ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D0OB00826E _journal_year 2020 _chemical_formula_moiety 'C25 H20 Br N O3' _chemical_formula_sum 'C25 H20 Br N O3' _chemical_formula_weight 462.33 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_date 2020-04-09 _audit_creation_method ; Olex2 1.3 (compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032) ; _audit_update_record ; 2020-05-14 deposited with the CCDC. 2020-05-20 downloaded from the CCDC. ; _cell_angle_alpha 103.149(4) _cell_angle_beta 104.108(4) _cell_angle_gamma 94.618(4) _cell_formula_units_Z 2 _cell_length_a 9.6348(5) _cell_length_b 10.2842(5) _cell_length_c 11.5040(5) _cell_measurement_reflns_used 3810 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 69.9270 _cell_measurement_theta_min 4.4540 _cell_volume 1065.31(9) _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 1.3 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXS (Sheldrick, 2008)' _diffrn_ambient_temperature 293(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 16.0733 _diffrn_detector_type Eos _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 -2.00 73.00 1.00 1.00 -- 54.00 -57.00 150.00 75 2 \w 28.00 107.00 1.00 1.00 -- 54.00-125.00 150.00 79 3 \w 80.00 106.00 1.00 1.00 -- 108.00-111.00 30.00 26 4 \w 57.00 113.00 1.00 1.00 -- 108.00-111.00 -90.00 56 5 \w 107.00 138.00 1.00 1.00 -- 108.00 -25.00-120.00 31 6 \w 142.00 178.00 1.00 1.00 -- 108.00 25.00-150.00 36 7 \w 145.00 176.00 1.00 1.00 -- 108.00 50.00 -90.00 31 8 \w 114.00 161.00 1.00 1.00 -- 108.00 63.00 60.00 47 9 \w 126.00 171.00 1.00 1.00 -- 108.00 25.00 150.00 45 10 \w 72.00 121.00 1.00 1.00 -- 54.00 57.00 30.00 49 11 \w 74.00 107.00 1.00 1.00 -- 108.00 25.00 150.00 33 12 \w 54.00 138.00 1.00 1.00 -- 108.00 -25.00 90.00 84 13 \w 89.00 121.00 1.00 1.00 -- 108.00 50.00 -90.00 32 14 \w 38.00 125.00 1.00 1.00 -- 108.00 -50.00 -60.00 87 15 \w 33.00 121.00 1.00 1.00 -- 54.00 57.00 120.00 88 16 \w 43.00 68.00 1.00 1.00 -- 0.00 57.00 120.00 25 17 \w -11.00 18.00 1.00 1.00 -- 0.00 -57.00 -30.00 29 18 \w -12.00 69.00 1.00 1.00 -- 54.00 -57.00 -30.00 81 19 \w 38.00 109.00 1.00 1.00 -- 108.00 -77.00 -90.00 71 20 \w 35.00 78.00 1.00 1.00 -- 108.00 -25.00-120.00 43 21 \w -14.00 68.00 1.00 1.00 -- 54.00 -57.00-120.00 82 22 \w 13.00 38.00 1.00 1.00 -- 0.00 57.00-150.00 25 23 \w 40.00 130.00 1.00 1.00 -- 108.00 -63.00 120.00 90 24 \w 38.00 116.00 1.00 1.00 -- 108.00-111.00 150.00 78 25 \w -21.00 23.00 1.00 1.00 -- 0.00 57.00 120.00 44 26 \w -57.00 -32.00 1.00 1.00 -- 0.00 -57.00 -30.00 25 27 \w 59.00 144.00 1.00 1.00 -- 108.00 178.00-180.00 85 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.1024457000 _diffrn_orient_matrix_UB_12 0.1056507000 _diffrn_orient_matrix_UB_13 -0.0265487000 _diffrn_orient_matrix_UB_21 -0.1297400000 _diffrn_orient_matrix_UB_22 0.0374803000 _diffrn_orient_matrix_UB_23 -0.0879539000 _diffrn_orient_matrix_UB_31 -0.0207256000 _diffrn_orient_matrix_UB_32 0.1076963000 _diffrn_orient_matrix_UB_33 0.1093550000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0179 _diffrn_reflns_av_unetI/netI 0.0219 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 6650 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 66.584 _diffrn_reflns_theta_max 66.584 _diffrn_reflns_theta_min 4.099 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 2.843 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.57333 _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 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.441 _exptl_crystal_description block _exptl_crystal_F_000 472 _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.14 _refine_diff_density_max 0.537 _refine_diff_density_min -0.774 _refine_diff_density_rms 0.047 _refine_ls_extinction_coef 0.0079(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2018/3 (Sheldrick 2018)' _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 273 _refine_ls_number_reflns 3769 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.032 _refine_ls_R_factor_all 0.0409 _refine_ls_R_factor_gt 0.0377 _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^)+(0.0418P)^2^+0.6776P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0926 _refine_ls_wR_factor_ref 0.0952 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3459 _reflns_number_total 3769 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ob00826e2.cif _cod_data_source_block lsq_p192_3 _cod_original_cell_volume 1065.30(9) _cod_database_code 7157516 _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 0.692 _shelx_estimated_absorpt_t_min 0.561 _reflns_odcompleteness_completeness 100.00 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _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: C11(H11) 2.b Secondary CH2 refined with riding coordinates: C8(H8A,H8B) 2.c Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3), C5(H5), C6(H6), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25) 2.d Idealised Me refined as rotating group: C19(H19A,H19B,H19C) ; _shelx_res_file ; TITL lsq_P192_3 in P-1 #2 lsq_p192_3.res created by SHELXL-2018/3 at 10:57:50 on 09-Apr-2020 REM reset to P-1 #2 CELL 1.54184 9.63477 10.284185 11.50399 103.1494 104.1083 94.6181 ZERR 2 0.000484 0.000485 0.000518 0.0039 0.0041 0.004 LATT 1 SFAC C H Br N O UNIT 50 40 2 2 6 L.S. 4 0 0 PLAN 1 SIZE 0.14 0.19 0.23 CONF BOND $H HTAB fmap 2 53 acta MORE -1 SHEL 999 0.84 REM REM REM WGHT 0.041800 0.677600 EXTI 0.007903 FVAR 8.40723 BR1 3 0.238565 0.380198 0.663981 11.00000 0.04855 0.09056 = 0.08988 0.04512 0.00816 0.02161 O1 5 0.923575 0.352070 0.895677 11.00000 0.05461 0.06436 = 0.06368 0.03369 0.02121 0.00522 O2 5 1.031542 0.224800 1.014392 11.00000 0.03456 0.05652 = 0.06661 0.02682 0.01671 0.00502 O3 5 0.524289 0.181946 1.111953 11.00000 0.03125 0.07746 = 0.05413 0.01628 0.01098 0.00155 N1 4 0.752124 0.242445 1.259725 11.00000 0.03253 0.05942 = 0.03789 0.01213 0.01312 0.00869 C1 1 0.643924 0.237321 0.885776 11.00000 0.03845 0.04211 = 0.03361 0.01027 0.01408 0.00585 C2 1 0.619774 0.370864 0.916562 11.00000 0.04577 0.04308 = 0.03763 0.00659 0.01321 0.00726 AFIX 43 H2 2 0.685779 0.432560 0.982654 11.00000 -1.20000 AFIX 0 C3 1 0.500246 0.413496 0.851224 11.00000 0.05191 0.04881 = 0.04904 0.01640 0.02343 0.01717 AFIX 43 H3 2 0.485966 0.503309 0.871752 11.00000 -1.20000 AFIX 0 C4 1 0.402178 0.320683 0.754880 11.00000 0.03745 0.06135 = 0.04661 0.02571 0.01690 0.01373 C5 1 0.421415 0.187485 0.722493 11.00000 0.04362 0.05662 = 0.04346 0.01107 0.00457 0.00021 AFIX 43 H5 2 0.354007 0.126008 0.657279 11.00000 -1.20000 AFIX 0 C6 1 0.542793 0.146520 0.788613 11.00000 0.04476 0.04389 = 0.04427 0.00783 0.00907 0.00511 AFIX 43 H6 2 0.556671 0.056639 0.767481 11.00000 -1.20000 AFIX 0 C7 1 0.776674 0.197367 0.958297 11.00000 0.03640 0.03730 = 0.03497 0.00824 0.01119 0.00397 C8 1 0.776144 0.057336 0.979956 11.00000 0.03894 0.03760 = 0.04395 0.00990 0.00975 0.00396 AFIX 23 H8A 2 0.687858 -0.006201 0.941938 11.00000 -1.20000 H8B 2 0.864551 0.017517 0.984000 11.00000 -1.20000 AFIX 0 C9 1 0.775329 0.173042 1.084462 11.00000 0.03258 0.04184 = 0.03736 0.01246 0.01053 0.00181 C10 1 0.654626 0.195989 1.144888 11.00000 0.03582 0.04726 = 0.04201 0.01469 0.01156 0.00335 C11 1 0.883330 0.229829 1.213648 11.00000 0.03158 0.04329 = 0.03820 0.01087 0.01331 0.00256 AFIX 13 H11 2 0.935583 0.318369 1.220949 11.00000 -1.20000 AFIX 0 C12 1 0.982947 0.139742 1.265478 11.00000 0.03682 0.04412 = 0.03399 0.01038 0.01219 0.00561 C13 1 1.130221 0.180791 1.306728 11.00000 0.03770 0.05003 = 0.05674 0.01398 0.01117 0.00452 AFIX 43 H13 2 1.168205 0.264971 1.302201 11.00000 -1.20000 AFIX 0 C14 1 1.222176 0.097565 1.354916 11.00000 0.03792 0.07172 = 0.06949 0.01743 0.00723 0.01368 AFIX 43 H14 2 1.321377 0.126133 1.382098 11.00000 -1.20000 AFIX 0 C15 1 1.167660 -0.026825 1.362757 11.00000 0.06572 0.06411 = 0.06429 0.02349 0.01389 0.02710 AFIX 43 H15 2 1.229324 -0.082150 1.395914 11.00000 -1.20000 AFIX 0 C16 1 1.022573 -0.068163 1.321514 11.00000 0.07258 0.05697 = 0.08361 0.03602 0.01698 0.00878 AFIX 43 H16 2 0.985187 -0.152577 1.325966 11.00000 -1.20000 AFIX 0 C17 1 0.930025 0.013905 1.273039 11.00000 0.04487 0.05776 = 0.07182 0.02800 0.01182 -0.00011 AFIX 43 H17 2 0.831074 -0.015915 1.245218 11.00000 -1.20000 AFIX 0 C18 1 0.916313 0.267048 0.950699 11.00000 0.04129 0.04101 = 0.03811 0.00769 0.01564 0.00509 C19 1 1.170702 0.292301 1.018028 11.00000 0.03972 0.07106 = 0.09322 0.02991 0.02169 -0.00166 AFIX 137 H19A 2 1.180482 0.278924 0.935217 11.00000 -1.50000 H19B 2 1.246123 0.255702 1.066403 11.00000 -1.50000 H19C 2 1.177890 0.387090 1.054880 11.00000 -1.50000 AFIX 0 C20 1 0.737082 0.292300 1.379418 11.00000 0.04307 0.04508 = 0.04132 0.01648 0.01796 0.01036 C21 1 0.600210 0.300290 1.397134 11.00000 0.04320 0.07974 = 0.05286 0.01698 0.02100 0.00559 AFIX 43 H21 2 0.518273 0.271127 1.330340 11.00000 -1.20000 AFIX 0 C22 1 0.587255 0.352112 1.515247 11.00000 0.05758 0.09380 = 0.06632 0.02005 0.04008 0.01358 AFIX 43 H22 2 0.495896 0.358603 1.527515 11.00000 -1.20000 AFIX 0 C23 1 0.707873 0.394314 1.615127 11.00000 0.07564 0.07932 = 0.04635 0.01591 0.03260 0.01584 AFIX 43 H23 2 0.697955 0.427836 1.694425 11.00000 -1.20000 AFIX 0 C24 1 0.841966 0.386517 1.596731 11.00000 0.06090 0.06691 = 0.04103 0.01146 0.01279 0.01547 AFIX 43 H24 2 0.923479 0.415277 1.663966 11.00000 -1.20000 AFIX 0 C25 1 0.858137 0.336323 1.479216 11.00000 0.04391 0.06097 = 0.04277 0.01360 0.01397 0.01512 AFIX 43 H25 2 0.950006 0.332255 1.467505 11.00000 -1.20000 AFIX 0 HKLF 4 REM lsq_P192_3 in P-1 #2 REM wR2 = 0.0952, GooF = S = 1.032, Restrained GooF = 1.032 for all data REM R1 = 0.0377 for 3459 Fo > 4sig(Fo) and 0.0409 for all 3769 data REM 273 parameters refined using 0 restraints END WGHT 0.0415 0.6811 REM Instructions for potential hydrogen bonds HTAB C21 O3 EQIV $1 x+1, y, z+1 HTAB C25 Br1_$1 REM Highest difference peak 0.537, deepest hole -0.774, 1-sigma level 0.047 Q1 1 0.2282 0.2971 0.6365 11.00000 0.05 0.54 ; _shelx_res_checksum 58105 _olex2_date_sample_data_collection 2020-04-07 _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 1.460 _oxdiff_exptl_absorpt_empirical_full_min 0.705 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' 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 0.23857(3) 0.38020(4) 0.66398(3) 0.07386(16) Uani 1 1 d . . . . . O1 O 0.9236(2) 0.35207(19) 0.89568(17) 0.0572(5) Uani 1 1 d . . . . . O2 O 1.03154(17) 0.22480(17) 1.01439(17) 0.0502(4) Uani 1 1 d . . . . . O3 O 0.52429(17) 0.18195(19) 1.11195(16) 0.0548(4) Uani 1 1 d . . . . . N1 N 0.75212(19) 0.2424(2) 1.25973(17) 0.0426(4) Uani 1 1 d . . . . . C1 C 0.6439(2) 0.2373(2) 0.88578(19) 0.0372(5) Uani 1 1 d . . . . . C2 C 0.6198(3) 0.3709(2) 0.9166(2) 0.0424(5) Uani 1 1 d . . . . . H2 H 0.685779 0.432560 0.982654 0.051 Uiso 1 1 calc R U . . . C3 C 0.5002(3) 0.4135(2) 0.8512(2) 0.0469(5) Uani 1 1 d . . . . . H3 H 0.485966 0.503309 0.871752 0.056 Uiso 1 1 calc R U . . . C4 C 0.4022(2) 0.3207(3) 0.7549(2) 0.0451(5) Uani 1 1 d . . . . . C5 C 0.4214(3) 0.1875(3) 0.7225(2) 0.0499(6) Uani 1 1 d . . . . . H5 H 0.354007 0.126008 0.657279 0.060 Uiso 1 1 calc R U . . . C6 C 0.5428(3) 0.1465(2) 0.7886(2) 0.0455(5) Uani 1 1 d . . . . . H6 H 0.556671 0.056639 0.767481 0.055 Uiso 1 1 calc R U . . . C7 C 0.7767(2) 0.1974(2) 0.95830(19) 0.0362(4) Uani 1 1 d . . . . . C8 C 0.7761(2) 0.0573(2) 0.9800(2) 0.0406(5) Uani 1 1 d . . . . . H8A H 0.687858 -0.006201 0.941938 0.049 Uiso 1 1 calc R U . . . H8B H 0.864551 0.017517 0.984000 0.049 Uiso 1 1 calc R U . . . C9 C 0.7753(2) 0.1730(2) 1.08446(19) 0.0369(5) Uani 1 1 d . . . . . C10 C 0.6546(2) 0.1960(2) 1.1449(2) 0.0411(5) Uani 1 1 d . . . . . C11 C 0.8833(2) 0.2298(2) 1.21365(19) 0.0371(5) Uani 1 1 d . . . . . H11 H 0.935583 0.318369 1.220949 0.044 Uiso 1 1 calc R U . . . C12 C 0.9829(2) 0.1397(2) 1.26548(19) 0.0378(5) Uani 1 1 d . . . . . C13 C 1.1302(3) 0.1808(3) 1.3067(2) 0.0485(5) Uani 1 1 d . . . . . H13 H 1.168205 0.264971 1.302201 0.058 Uiso 1 1 calc R U . . . C14 C 1.2222(3) 0.0976(3) 1.3549(3) 0.0608(7) Uani 1 1 d . . . . . H14 H 1.321377 0.126133 1.382098 0.073 Uiso 1 1 calc R U . . . C15 C 1.1677(3) -0.0268(3) 1.3628(3) 0.0631(7) Uani 1 1 d . . . . . H15 H 1.229324 -0.082150 1.395914 0.076 Uiso 1 1 calc R U . . . C16 C 1.0226(4) -0.0682(3) 1.3215(3) 0.0688(8) Uani 1 1 d . . . . . H16 H 0.985187 -0.152577 1.325966 0.083 Uiso 1 1 calc R U . . . C17 C 0.9300(3) 0.0139(3) 1.2730(3) 0.0574(7) Uani 1 1 d . . . . . H17 H 0.831074 -0.015915 1.245218 0.069 Uiso 1 1 calc R U . . . C18 C 0.9163(2) 0.2670(2) 0.9507(2) 0.0397(5) Uani 1 1 d . . . . . C19 C 1.1707(3) 0.2923(3) 1.0180(3) 0.0664(8) Uani 1 1 d . . . . . H19A H 1.180482 0.278924 0.935217 0.100 Uiso 1 1 calc R U . . . H19B H 1.246123 0.255702 1.066403 0.100 Uiso 1 1 calc R U . . . H19C H 1.177890 0.387090 1.054880 0.100 Uiso 1 1 calc R U . . . C20 C 0.7371(2) 0.2923(2) 1.3794(2) 0.0408(5) Uani 1 1 d . . . . . C21 C 0.6002(3) 0.3003(3) 1.3971(3) 0.0573(7) Uani 1 1 d . . . . . H21 H 0.518273 0.271127 1.330340 0.069 Uiso 1 1 calc R U . . . C22 C 0.5873(3) 0.3521(3) 1.5152(3) 0.0683(8) Uani 1 1 d . . . . . H22 H 0.495896 0.358603 1.527515 0.082 Uiso 1 1 calc R U . . . C23 C 0.7079(3) 0.3943(3) 1.6151(3) 0.0639(7) Uani 1 1 d . . . . . H23 H 0.697955 0.427836 1.694425 0.077 Uiso 1 1 calc R U . . . C24 C 0.8420(3) 0.3865(3) 1.5967(2) 0.0565(6) Uani 1 1 d . . . . . H24 H 0.923479 0.415277 1.663966 0.068 Uiso 1 1 calc R U . . . C25 C 0.8581(3) 0.3363(3) 1.4792(2) 0.0483(5) Uani 1 1 d . . . . . H25 H 0.950006 0.332255 1.467505 0.058 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 0.0485(2) 0.0906(3) 0.0899(3) 0.0451(2) 0.00816(16) 0.02161(16) O1 0.0546(10) 0.0644(11) 0.0637(11) 0.0337(9) 0.0212(9) 0.0052(8) O2 0.0346(8) 0.0565(10) 0.0666(11) 0.0268(8) 0.0167(8) 0.0050(7) O3 0.0312(9) 0.0775(12) 0.0541(10) 0.0163(9) 0.0110(7) 0.0016(8) N1 0.0325(9) 0.0594(11) 0.0379(10) 0.0121(8) 0.0131(8) 0.0087(8) C1 0.0385(11) 0.0421(11) 0.0336(10) 0.0103(9) 0.0141(9) 0.0058(9) C2 0.0458(12) 0.0431(12) 0.0376(11) 0.0066(9) 0.0132(10) 0.0073(10) C3 0.0519(14) 0.0488(13) 0.0490(13) 0.0164(11) 0.0234(11) 0.0172(11) C4 0.0374(12) 0.0614(14) 0.0466(13) 0.0257(11) 0.0169(10) 0.0137(10) C5 0.0436(13) 0.0566(14) 0.0435(13) 0.0111(11) 0.0046(10) 0.0002(11) C6 0.0448(13) 0.0439(12) 0.0443(12) 0.0078(10) 0.0091(10) 0.0051(10) C7 0.0364(11) 0.0373(10) 0.0350(11) 0.0082(8) 0.0112(9) 0.0040(8) C8 0.0389(11) 0.0376(11) 0.0440(12) 0.0099(9) 0.0097(9) 0.0040(9) C9 0.0326(10) 0.0418(11) 0.0374(11) 0.0125(9) 0.0105(9) 0.0018(8) C10 0.0358(12) 0.0473(12) 0.0420(12) 0.0147(10) 0.0116(9) 0.0033(9) C11 0.0316(10) 0.0433(11) 0.0382(11) 0.0109(9) 0.0133(9) 0.0026(8) C12 0.0368(11) 0.0441(11) 0.0340(10) 0.0104(9) 0.0122(9) 0.0056(9) C13 0.0377(12) 0.0500(13) 0.0567(14) 0.0140(11) 0.0112(10) 0.0045(10) C14 0.0379(13) 0.0717(18) 0.0695(18) 0.0174(14) 0.0072(12) 0.0137(12) C15 0.0657(18) 0.0641(17) 0.0643(17) 0.0235(14) 0.0139(14) 0.0271(14) C16 0.073(2) 0.0570(16) 0.084(2) 0.0360(15) 0.0170(16) 0.0088(14) C17 0.0449(14) 0.0578(15) 0.0718(17) 0.0280(13) 0.0118(12) -0.0001(11) C18 0.0413(12) 0.0410(11) 0.0381(11) 0.0077(9) 0.0156(9) 0.0051(9) C19 0.0397(14) 0.0711(18) 0.093(2) 0.0299(16) 0.0217(14) -0.0017(12) C20 0.0431(12) 0.0451(12) 0.0413(12) 0.0165(9) 0.0180(10) 0.0104(9) C21 0.0432(13) 0.0797(18) 0.0529(15) 0.0170(13) 0.0210(12) 0.0056(12) C22 0.0576(17) 0.094(2) 0.0663(18) 0.0201(16) 0.0401(15) 0.0136(15) C23 0.0756(19) 0.0793(19) 0.0464(14) 0.0159(13) 0.0326(14) 0.0158(15) C24 0.0609(16) 0.0669(16) 0.0410(13) 0.0115(12) 0.0128(12) 0.0155(13) C25 0.0439(13) 0.0610(14) 0.0428(12) 0.0136(11) 0.0140(10) 0.0151(11) 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' N N 0.0311 0.0180 '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 C18 O2 C19 115.8(2) . . ? C10 N1 C11 95.53(16) . . ? C10 N1 C20 133.27(19) . . ? C20 N1 C11 131.12(18) . . ? C2 C1 C7 119.03(19) . . ? C6 C1 C2 118.4(2) . . ? C6 C1 C7 122.6(2) . . ? C1 C2 H2 119.3 . . ? C3 C2 C1 121.3(2) . . ? C3 C2 H2 119.3 . . ? C2 C3 H3 120.6 . . ? C2 C3 C4 118.7(2) . . ? C4 C3 H3 120.6 . . ? C3 C4 Br1 118.61(18) . . ? C5 C4 Br1 119.74(19) . . ? C5 C4 C3 121.6(2) . . ? C4 C5 H5 120.6 . . ? C4 C5 C6 118.9(2) . . ? C6 C5 H5 120.6 . . ? C1 C6 H6 119.5 . . ? C5 C6 C1 121.0(2) . . ? C5 C6 H6 119.5 . . ? C1 C7 C8 120.92(18) . . ? C1 C7 C9 117.57(17) . . ? C1 C7 C18 114.62(18) . . ? C8 C7 C9 58.50(14) . . ? C18 C7 C8 117.57(19) . . ? C18 C7 C9 116.12(18) . . ? C7 C8 H8A 117.6 . . ? C7 C8 H8B 117.6 . . ? H8A C8 H8B 114.8 . . ? C9 C8 C7 61.24(14) . . ? C9 C8 H8A 117.6 . . ? C9 C8 H8B 117.6 . . ? C7 C9 C11 130.88(18) . . ? C8 C9 C7 60.26(14) . . ? C8 C9 C10 126.40(19) . . ? C8 C9 C11 131.04(19) . . ? C10 C9 C7 124.96(19) . . ? C10 C9 C11 88.31(16) . . ? O3 C10 N1 132.2(2) . . ? O3 C10 C9 136.9(2) . . ? N1 C10 C9 90.95(17) . . ? N1 C11 C9 85.16(15) . . ? N1 C11 H11 111.6 . . ? N1 C11 C12 115.68(17) . . ? C9 C11 H11 111.6 . . ? C12 C11 C9 118.66(18) . . ? C12 C11 H11 111.6 . . ? C13 C12 C11 120.6(2) . . ? C13 C12 C17 118.3(2) . . ? C17 C12 C11 121.1(2) . . ? C12 C13 H13 119.7 . . ? C12 C13 C14 120.5(2) . . ? C14 C13 H13 119.7 . . ? C13 C14 H14 119.8 . . ? C15 C14 C13 120.4(3) . . ? C15 C14 H14 119.8 . . ? C14 C15 H15 120.4 . . ? C16 C15 C14 119.3(3) . . ? C16 C15 H15 120.4 . . ? C15 C16 H16 119.6 . . ? C15 C16 C17 120.7(3) . . ? C17 C16 H16 119.6 . . ? C12 C17 C16 120.7(3) . . ? C12 C17 H17 119.6 . . ? C16 C17 H17 119.6 . . ? O1 C18 O2 123.9(2) . . ? O1 C18 C7 124.0(2) . . ? O2 C18 C7 112.12(19) . . ? O2 C19 H19A 109.5 . . ? O2 C19 H19B 109.5 . . ? O2 C19 H19C 109.5 . . ? H19A C19 H19B 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C21 C20 N1 119.9(2) . . ? C25 C20 N1 120.2(2) . . ? C25 C20 C21 120.0(2) . . ? C20 C21 H21 120.4 . . ? C22 C21 C20 119.2(3) . . ? C22 C21 H21 120.4 . . ? C21 C22 H22 119.5 . . ? C23 C22 C21 120.9(3) . . ? C23 C22 H22 119.5 . . ? C22 C23 H23 120.3 . . ? C24 C23 C22 119.5(2) . . ? C24 C23 H23 120.3 . . ? C23 C24 H24 119.6 . . ? C23 C24 C25 120.8(3) . . ? C25 C24 H24 119.6 . . ? C20 C25 C24 119.7(2) . . ? C20 C25 H25 120.2 . . ? C24 C25 H25 120.2 . . ? 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 1.896(2) . ? O1 C18 1.197(3) . ? O2 C18 1.336(3) . ? O2 C19 1.446(3) . ? O3 C10 1.206(3) . ? N1 C10 1.375(3) . ? N1 C11 1.489(3) . ? N1 C20 1.403(3) . ? C1 C2 1.391(3) . ? C1 C6 1.385(3) . ? C1 C7 1.490(3) . ? C2 H2 0.9300 . ? C2 C3 1.376(3) . ? C3 H3 0.9300 . ? C3 C4 1.377(4) . ? C4 C5 1.375(4) . ? C5 H5 0.9300 . ? C5 C6 1.384(3) . ? C6 H6 0.9300 . ? C7 C8 1.516(3) . ? C7 C9 1.531(3) . ? C7 C18 1.504(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C8 C9 1.489(3) . ? C9 C10 1.502(3) . ? C9 C11 1.545(3) . ? C11 H11 0.9800 . ? C11 C12 1.500(3) . ? C12 C13 1.379(3) . ? C12 C17 1.382(3) . ? C13 H13 0.9300 . ? C13 C14 1.387(4) . ? C14 H14 0.9300 . ? C14 C15 1.374(4) . ? C15 H15 0.9300 . ? C15 C16 1.360(4) . ? C16 H16 0.9300 . ? C16 C17 1.382(4) . ? C17 H17 0.9300 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 C21 1.389(3) . ? C20 C25 1.382(3) . ? C21 H21 0.9300 . ? C21 C22 1.382(4) . ? C22 H22 0.9300 . ? C22 C23 1.378(4) . ? C23 H23 0.9300 . ? C23 C24 1.365(4) . ? C24 H24 0.9300 . ? C24 C25 1.384(3) . ? C25 H25 0.9300 . ? 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 178.90(18) . . . . ? N1 C11 C12 C13 -134.1(2) . . . . ? N1 C11 C12 C17 46.0(3) . . . . ? N1 C20 C21 C22 -178.7(3) . . . . ? N1 C20 C25 C24 179.4(2) . . . . ? C1 C2 C3 C4 1.0(3) . . . . ? C1 C7 C8 C9 -105.4(2) . . . . ? C1 C7 C9 C8 111.1(2) . . . . ? C1 C7 C9 C10 -4.7(3) . . . . ? C1 C7 C9 C11 -128.5(2) . . . . ? C1 C7 C18 O1 2.9(3) . . . . ? C1 C7 C18 O2 -178.23(17) . . . . ? C2 C1 C6 C5 0.8(3) . . . . ? C2 C1 C7 C8 147.6(2) . . . . ? C2 C1 C7 C9 79.6(2) . . . . ? C2 C1 C7 C18 -62.2(3) . . . . ? C2 C3 C4 Br1 -179.38(17) . . . . ? C2 C3 C4 C5 -0.3(3) . . . . ? C3 C4 C5 C6 -0.2(4) . . . . ? C4 C5 C6 C1 -0.1(4) . . . . ? C6 C1 C2 C3 -1.3(3) . . . . ? C6 C1 C7 C8 -32.3(3) . . . . ? C6 C1 C7 C9 -100.3(2) . . . . ? C6 C1 C7 C18 118.0(2) . . . . ? C7 C1 C2 C3 178.9(2) . . . . ? C7 C1 C6 C5 -179.4(2) . . . . ? C7 C8 C9 C10 113.5(2) . . . . ? C7 C8 C9 C11 -120.1(2) . . . . ? C7 C9 C10 O3 37.1(4) . . . . ? C7 C9 C10 N1 -142.8(2) . . . . ? C7 C9 C11 N1 138.7(2) . . . . ? C7 C9 C11 C12 -104.6(3) . . . . ? C8 C7 C9 C10 -115.7(2) . . . . ? C8 C7 C9 C11 120.4(3) . . . . ? C8 C7 C18 O1 154.2(2) . . . . ? C8 C7 C18 O2 -27.0(3) . . . . ? C8 C9 C10 O3 -39.2(4) . . . . ? C8 C9 C10 N1 140.9(2) . . . . ? C8 C9 C11 N1 -138.0(2) . . . . ? C8 C9 C11 C12 -21.3(3) . . . . ? C9 C7 C18 O1 -139.4(2) . . . . ? C9 C7 C18 O2 39.4(3) . . . . ? C9 C11 C12 C13 126.9(2) . . . . ? C9 C11 C12 C17 -53.0(3) . . . . ? C10 N1 C11 C9 -1.74(17) . . . . ? C10 N1 C11 C12 -121.3(2) . . . . ? C10 N1 C20 C21 0.5(4) . . . . ? C10 N1 C20 C25 -178.0(2) . . . . ? C10 C9 C11 N1 1.59(16) . . . . ? C10 C9 C11 C12 118.29(19) . . . . ? C11 N1 C10 O3 -178.1(3) . . . . ? C11 N1 C10 C9 1.79(18) . . . . ? C11 N1 C20 C21 176.3(2) . . . . ? C11 N1 C20 C25 -2.2(4) . . . . ? C11 C9 C10 O3 178.2(3) . . . . ? C11 C9 C10 N1 -1.72(17) . . . . ? C11 C12 C13 C14 179.8(2) . . . . ? C11 C12 C17 C16 -179.7(3) . . . . ? C12 C13 C14 C15 -0.3(4) . . . . ? C13 C12 C17 C16 0.4(4) . . . . ? C13 C14 C15 C16 0.7(5) . . . . ? C14 C15 C16 C17 -0.5(5) . . . . ? C15 C16 C17 C12 0.0(5) . . . . ? C17 C12 C13 C14 -0.2(4) . . . . ? C18 C7 C8 C9 105.2(2) . . . . ? C18 C7 C9 C8 -107.7(2) . . . . ? C18 C7 C9 C10 136.5(2) . . . . ? C18 C7 C9 C11 12.7(3) . . . . ? C19 O2 C18 O1 2.3(3) . . . . ? C19 O2 C18 C7 -176.5(2) . . . . ? C20 N1 C10 O3 -1.3(5) . . . . ? C20 N1 C10 C9 178.6(2) . . . . ? C20 N1 C11 C9 -178.7(2) . . . . ? C20 N1 C11 C12 61.8(3) . . . . ? C20 C21 C22 C23 -0.7(5) . . . . ? C21 C20 C25 C24 0.9(4) . . . . ? C21 C22 C23 C24 0.9(5) . . . . ? C22 C23 C24 C25 -0.3(5) . . . . ? C23 C24 C25 C20 -0.6(4) . . . . ? C25 C20 C21 C22 -0.2(4) . . . . ?