#------------------------------------------------------------------------------ #$Date: 2018-01-11 04:27:38 +0200 (Thu, 11 Jan 2018) $ #$Revision: 205057 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/54/86/1548657.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_1548657 loop_ _publ_author_name 'Uno, Brice E.' 'Dicken, Rachel D.' 'Redfern, Louis R.' 'Stern, Charlotte M.' 'Krzywicki, Greg G.' 'Scheidt, Karl A.' _publ_section_title ; Calcium(ii)-catalyzed enantioselective conjugate additions of amines ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/C7SC05205G _journal_year 2018 _chemical_absolute_configuration ad _chemical_formula_moiety 'C18 H17 Br N2 O2' _chemical_formula_sum 'C18 H17 Br N2 O2' _chemical_formula_weight 373.24 _space_group_crystal_system triclinic _space_group_IT_number 1 _space_group_name_Hall 'P 1' _space_group_name_H-M_alt 'P 1' _symmetry_space_group_name_Hall 'P 1' _symmetry_space_group_name_H-M 'P 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary direct _audit_creation_date 2016-11-19 _audit_creation_method ; Olex2 1.2 (compiled Nov 7 2016 13:22:42 for OlexSys, GUI svn.r5261) ; _audit_update_record ; 2017-02-06 deposited with the CCDC. 2017-12-18 downloaded from the CCDC. ; _cell_angle_alpha 100.603(8) _cell_angle_beta 92.652(8) _cell_angle_gamma 94.550(9) _cell_formula_units_Z 1 _cell_length_a 4.6810(5) _cell_length_b 6.1091(7) _cell_length_c 14.2048(16) _cell_measurement_reflns_used 2766 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 66.66 _cell_measurement_theta_min 3.17 _cell_volume 397.25(8) _computing_cell_refinement 'SAINT v8.37A (Bruker, 2015)' _computing_data_reduction 'SAINT v8.37A (Bruker, 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 'ShelXS (Sheldrick, 2008)' _diffrn_ambient_temperature 100.01 _diffrn_measured_fraction_theta_full 0.943 _diffrn_measured_fraction_theta_max 0.943 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0358 _diffrn_reflns_av_unetI/netI 0.0527 _diffrn_reflns_Laue_measured_fraction_full 0.943 _diffrn_reflns_Laue_measured_fraction_max 0.943 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 4192 _diffrn_reflns_point_group_measured_fraction_full 0.848 _diffrn_reflns_point_group_measured_fraction_max 0.848 _diffrn_reflns_theta_full 66.660 _diffrn_reflns_theta_max 66.660 _diffrn_reflns_theta_min 3.171 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 3.621 _exptl_absorpt_correction_T_max 0.7528 _exptl_absorpt_correction_T_min 0.5785 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2014/5 (Bruker,2014) was used for absorption correction. wR2(int) was 0.1108 before and 0.0459 after correction. The Ratio of minimum to maximum transmission is 0.7685. The \l/2 correction factor is Not present. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.560 _exptl_crystal_description block _exptl_crystal_F_000 190 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: Hexanes/ethyl acetate' _exptl_crystal_size_max 0.135 _exptl_crystal_size_mid 0.134 _exptl_crystal_size_min 0.079 _refine_diff_density_max 0.613 _refine_diff_density_min -0.556 _refine_diff_density_rms 0.100 _refine_ls_abs_structure_details ; Flack x determined using 965 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.02(4) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.111 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 212 _refine_ls_number_reflns 2403 _refine_ls_number_restraints 3 _refine_ls_restrained_S_all 1.110 _refine_ls_R_factor_all 0.0517 _refine_ls_R_factor_gt 0.0485 _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^)+(0.0531P)^2^+1.4835P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1197 _refine_ls_wR_factor_ref 0.1266 _reflns_Friedel_coverage 0.799 _reflns_Friedel_fraction_full 0.753 _reflns_Friedel_fraction_max 0.753 _reflns_number_gt 2336 _reflns_number_total 2403 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7sc05205g2.cif _cod_data_source_block xrd0843 _cod_database_code 1548657 _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 0.763 _shelx_estimated_absorpt_t_min 0.641 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups 2.a Ternary CH refined with riding coordinates: C9(H9) 2.b Secondary CH2 refined with riding coordinates: C10(H11A,H11B), C12(H15A,H15B), C7(H21A,H21B) 2.c Aromatic/amide H refined with riding coordinates: C4(H6), C15(H8), C18(H10), C14(H12), C17(H14), C3(H16), C1(H17), C5(H18), C2(H20) ; _shelx_res_file ; TITL xrd0843 in P1 #1 xrd0843.res created by SHELXL-2016/6 at 11:50:30 on 19-Nov-2016 REM reset to P1 #1 CELL 1.54178 4.681 6.1091 14.2048 100.603 92.652 94.55 ZERR 1 0.0005 0.0007 0.0016 0.008 0.008 0.009 LATT -1 SFAC C H Br N O UNIT 18 17 1 2 2 L.S. 100 PLAN 20 SIZE 0.079 0.134 0.135 TEMP -173.14 BOND MORE -1 BOND $H CONF fmap 2 acta REM REM REM WGHT 0.053100 1.483500 FVAR 1.12024 BR1 3 1.109720 1.408580 0.632550 11.00000 0.02184 0.03492 = 0.02257 -0.00545 -0.00698 -0.00473 C1 1 0.821923 1.249774 0.538937 11.00000 0.01848 0.01846 = 0.01774 -0.00545 -0.00269 0.00097 O2 5 -0.292673 0.078505 0.151423 11.00000 0.02162 0.01511 = 0.02122 0.00456 0.00102 -0.00985 O3 5 0.408547 0.542186 0.063244 11.00000 0.02522 0.01986 = 0.02123 0.00134 0.00255 -0.00965 N4 4 0.290741 0.757571 0.257053 11.00000 0.01182 0.01679 = 0.01893 -0.00050 0.00042 -0.00754 C5 1 0.394858 1.028652 0.407206 11.00000 0.01722 0.01879 = 0.01131 -0.00344 0.00379 0.00110 C6 1 -0.487204 -0.215588 -0.158858 11.00000 0.02752 0.01435 = 0.02643 -0.00620 -0.00068 -0.00441 AFIX 43 H6 2 -0.598738 -0.355776 -0.170193 11.00000 -1.20000 AFIX 0 N7 4 0.063166 0.271040 0.089313 11.00000 0.01679 0.01948 = 0.01308 -0.00054 -0.00207 -0.00460 C8 1 0.725642 1.353531 0.468080 11.00000 0.01639 0.01688 = 0.02565 0.00071 0.00735 -0.00275 AFIX 43 H8 2 0.804301 1.499492 0.464067 11.00000 -1.20000 AFIX 0 C9 1 0.069683 0.629565 0.187862 11.00000 0.01536 0.01704 = 0.01652 0.00461 0.00221 -0.00388 AFIX 13 H9 2 -0.052666 0.734177 0.161724 11.00000 -1.20000 AFIX 0 C10 1 0.499155 0.927206 0.479708 11.00000 0.01657 0.01102 = 0.02633 -0.00154 0.00058 -0.00541 AFIX 43 H10 2 0.421798 0.781194 0.484171 11.00000 -1.20000 AFIX 0 C11 1 -0.119187 0.459438 0.228335 11.00000 0.01703 0.01236 = 0.01536 0.00342 -0.00222 -0.00023 AFIX 23 H11A 2 -0.031810 0.434050 0.289784 11.00000 -1.20000 H11B 2 -0.311961 0.511450 0.239378 11.00000 -1.20000 AFIX 0 C12 1 0.510315 1.242260 0.401720 11.00000 0.01674 0.01990 = 0.01682 0.00336 0.00113 -0.00010 AFIX 43 H12 2 0.441373 1.313122 0.352067 11.00000 -1.20000 AFIX 0 C13 1 -0.107219 0.038374 -0.068449 11.00000 0.02042 0.01368 = 0.01433 -0.00272 0.00374 -0.00004 C14 1 0.718730 1.038062 0.546949 11.00000 0.02341 0.02368 = 0.01679 -0.00093 -0.00209 0.00541 AFIX 43 H14 2 0.792777 0.968282 0.596220 11.00000 -1.20000 AFIX 0 C15 1 0.165148 0.908658 0.333520 11.00000 0.01631 0.01658 = 0.01896 -0.00007 -0.00023 -0.00262 AFIX 23 H15A 2 0.023578 0.821724 0.364996 11.00000 -1.20000 H15B 2 0.063168 1.019605 0.305403 11.00000 -1.20000 AFIX 0 C16 1 -0.539421 -0.060465 -0.215475 11.00000 0.02586 0.03341 = 0.01789 -0.00082 -0.00569 0.00614 AFIX 43 H16 2 -0.687487 -0.093066 -0.265339 11.00000 -1.20000 AFIX 0 C17 1 -0.160275 0.191782 -0.126040 11.00000 0.01992 0.01895 = 0.01783 0.00368 0.00046 0.00158 AFIX 43 H17 2 -0.048738 0.331916 -0.115394 11.00000 -1.20000 AFIX 0 C18 1 -0.270032 -0.167372 -0.084549 11.00000 0.02387 0.01289 = 0.02223 0.00225 -0.00230 -0.00303 AFIX 43 H18 2 -0.234508 -0.274294 -0.045581 11.00000 -1.20000 AFIX 0 C19 1 -0.138907 0.248439 0.153230 11.00000 0.01576 0.01959 = 0.01364 0.00601 -0.00525 -0.00091 C20 1 -0.375059 0.142768 -0.199252 11.00000 0.03048 0.02054 = 0.02411 0.00093 -0.00532 0.00510 AFIX 43 H20 2 -0.409509 0.249359 -0.238485 11.00000 -1.20000 AFIX 0 C21 1 0.129292 0.091893 0.010081 11.00000 0.02119 0.01562 = 0.01804 -0.00093 -0.00134 -0.00295 AFIX 23 H21A 2 0.159978 -0.044765 0.035978 11.00000 -1.20000 H21B 2 0.309691 0.139070 -0.017274 11.00000 -1.20000 AFIX 0 C22 1 0.209942 0.487119 0.105855 11.00000 0.02185 0.01854 = 0.01439 0.00739 -0.00337 -0.00262 H4 2 0.402071 0.827104 0.232800 11.00000 0.02897 HKLF 4 REM xrd0843 in P1 #1 REM R1 = 0.0485 for 2336 Fo > 4sig(Fo) and 0.0517 for all 2403 data REM 212 parameters refined using 3 restraints END WGHT 0.0531 1.4836 REM Highest difference peak 0.613, deepest hole -0.556, 1-sigma level 0.100 Q1 1 1.2783 1.3323 0.6993 11.00000 0.05 0.61 Q2 1 1.1881 1.4679 0.5657 11.00000 0.05 0.58 Q3 1 0.9426 1.4964 0.5770 11.00000 0.05 0.57 Q4 1 1.0356 1.3536 0.7040 11.00000 0.05 0.56 Q5 1 1.2923 1.4537 0.6265 11.00000 0.05 0.51 Q6 1 0.9249 1.3677 0.6485 11.00000 0.05 0.48 Q7 1 1.0966 1.4983 0.6832 11.00000 0.05 0.43 Q8 1 1.1281 1.3079 0.5853 11.00000 0.05 0.42 Q9 1 0.5652 1.3051 0.4794 11.00000 0.05 0.36 Q10 1 1.5139 1.4403 0.6517 11.00000 0.05 0.34 Q11 1 0.7468 1.0071 0.6346 11.00000 0.05 0.33 Q12 1 0.1470 0.6350 0.5239 11.00000 0.05 0.32 Q13 1 -0.3705 0.0323 0.2031 11.00000 0.05 0.31 Q14 1 0.3708 1.3736 0.3613 11.00000 0.05 0.30 Q15 1 0.6422 0.9518 0.4656 11.00000 0.05 0.30 Q16 1 -0.4602 0.0579 0.2005 11.00000 0.05 0.30 Q17 1 0.1524 0.2506 0.0463 11.00000 0.05 0.30 Q18 1 0.6775 0.9901 0.4882 11.00000 0.05 0.29 Q19 1 -0.9423 0.1172 -0.2767 11.00000 0.05 0.29 Q20 1 0.8910 0.9423 0.6256 11.00000 0.05 0.29 ; _shelx_res_checksum 19987 _shelx_shelxl_version_number 2016/6 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz '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 Br1 Br 1.10972(7) 1.40858(7) 0.63255(6) 0.0285(3) Uani 1 1 d . C1 C 0.822(2) 1.2498(17) 0.5389(6) 0.020(2) Uani 1 1 d . O2 O -0.2927(14) 0.0785(12) 0.1514(4) 0.0198(15) Uani 1 1 d . O3 O 0.4085(16) 0.5422(13) 0.0632(6) 0.0230(16) Uani 1 1 d . N4 N 0.2907(19) 0.7576(15) 0.2571(6) 0.0168(17) Uani 1 1 d . C5 C 0.395(2) 1.0287(17) 0.4072(6) 0.017(2) Uani 1 1 d . C6 C -0.487(2) -0.2156(18) -0.1589(7) 0.024(2) Uani 1 1 d . H6 H -0.598738 -0.355776 -0.170193 0.029 Uiso 1 1 calc R N7 N 0.0632(18) 0.2710(16) 0.0893(6) 0.0173(19) Uani 1 1 d . C8 C 0.726(2) 1.3535(18) 0.4681(7) 0.020(2) Uani 1 1 d . H8 H 0.804301 1.499492 0.464067 0.024 Uiso 1 1 calc R C9 C 0.070(2) 0.6296(19) 0.1879(7) 0.016(2) Uani 1 1 d . H9 H -0.052666 0.734177 0.161724 0.020 Uiso 1 1 calc R C10 C 0.499(2) 0.9272(17) 0.4797(7) 0.019(2) Uani 1 1 d . H10 H 0.421798 0.781194 0.484171 0.023 Uiso 1 1 calc R C11 C -0.119(2) 0.4594(17) 0.2283(6) 0.015(2) Uani 1 1 d . H11A H -0.031810 0.434050 0.289784 0.018 Uiso 1 1 calc R H11B H -0.311961 0.511450 0.239378 0.018 Uiso 1 1 calc R C12 C 0.510(2) 1.2423(17) 0.4017(6) 0.018(2) Uani 1 1 d . H12 H 0.441373 1.313122 0.352067 0.022 Uiso 1 1 calc R C13 C -0.107(2) 0.0384(17) -0.0684(6) 0.017(2) Uani 1 1 d . C14 C 0.719(2) 1.0381(18) 0.5469(7) 0.022(2) Uani 1 1 d . H14 H 0.792777 0.968282 0.596220 0.026 Uiso 1 1 calc R C15 C 0.165(2) 0.9087(17) 0.3335(6) 0.018(2) Uani 1 1 d . H15A H 0.023578 0.821724 0.364996 0.022 Uiso 1 1 calc R H15B H 0.063168 1.019605 0.305403 0.022 Uiso 1 1 calc R C16 C -0.539(2) -0.0605(19) -0.2155(7) 0.026(2) Uani 1 1 d . H16 H -0.687487 -0.093066 -0.265339 0.032 Uiso 1 1 calc R C17 C -0.160(2) 0.1918(17) -0.1260(6) 0.019(2) Uani 1 1 d . H17 H -0.048738 0.331916 -0.115394 0.023 Uiso 1 1 calc R C18 C -0.270(2) -0.1674(17) -0.0845(7) 0.020(2) Uani 1 1 d . H18 H -0.234508 -0.274294 -0.045581 0.024 Uiso 1 1 calc R C19 C -0.139(2) 0.2484(19) 0.1532(7) 0.016(2) Uani 1 1 d . C20 C -0.375(2) 0.1428(18) -0.1993(7) 0.026(2) Uani 1 1 d . H20 H -0.409509 0.249359 -0.238485 0.031 Uiso 1 1 calc R C21 C 0.129(2) 0.0919(17) 0.0101(7) 0.019(2) Uani 1 1 d . H21A H 0.159978 -0.044765 0.035978 0.023 Uiso 1 1 calc R H21B H 0.309691 0.139070 -0.017274 0.023 Uiso 1 1 calc R C22 C 0.210(2) 0.4871(18) 0.1059(6) 0.018(2) Uani 1 1 d . H4 H 0.40(3) 0.83(2) 0.233(9) 0.03(3) Uiso 1 1 d . 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 0.0218(5) 0.0349(7) 0.0226(5) -0.0055(4) -0.0070(3) -0.0047(4) C1 0.018(5) 0.018(6) 0.018(5) -0.005(4) -0.003(4) 0.001(4) O2 0.022(3) 0.015(4) 0.021(3) 0.005(3) 0.001(3) -0.010(3) O3 0.025(4) 0.020(5) 0.021(4) 0.001(3) 0.003(3) -0.010(3) N4 0.012(4) 0.017(5) 0.019(4) 0.000(3) 0.000(3) -0.008(4) C5 0.017(5) 0.019(6) 0.011(4) -0.003(4) 0.004(4) 0.001(4) C6 0.028(6) 0.014(6) 0.026(5) -0.006(4) -0.001(4) -0.004(4) N7 0.017(4) 0.019(6) 0.013(4) -0.001(3) -0.002(3) -0.005(4) C8 0.016(5) 0.017(6) 0.026(5) 0.001(4) 0.007(4) -0.003(4) C9 0.015(5) 0.017(6) 0.017(5) 0.005(4) 0.002(4) -0.004(4) C10 0.017(5) 0.011(5) 0.026(5) -0.002(4) 0.001(4) -0.005(4) C11 0.017(5) 0.012(6) 0.015(4) 0.003(4) -0.002(3) 0.000(4) C12 0.017(4) 0.020(6) 0.017(4) 0.003(4) 0.001(4) 0.000(4) C13 0.020(5) 0.014(6) 0.014(5) -0.003(4) 0.004(4) 0.000(4) C14 0.023(5) 0.024(7) 0.017(4) -0.001(4) -0.002(4) 0.005(5) C15 0.016(5) 0.017(6) 0.019(4) 0.000(4) 0.000(4) -0.003(4) C16 0.026(5) 0.033(7) 0.018(5) -0.001(4) -0.006(4) 0.006(5) C17 0.020(5) 0.019(6) 0.018(4) 0.004(4) 0.000(4) 0.002(4) C18 0.024(5) 0.013(6) 0.022(5) 0.002(4) -0.002(4) -0.003(4) C19 0.016(5) 0.020(7) 0.014(5) 0.006(4) -0.005(4) -0.001(5) C20 0.030(6) 0.021(6) 0.024(5) 0.001(4) -0.005(4) 0.005(5) C21 0.021(5) 0.016(6) 0.018(5) -0.001(4) -0.001(4) -0.003(4) C22 0.022(5) 0.019(6) 0.014(5) 0.007(4) -0.003(4) -0.003(5) 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 C8 C1 Br1 118.6(8) C8 C1 C14 122.8(9) C14 C1 Br1 118.6(7) C9 N4 C15 111.7(8) C9 N4 H4 112(10) C15 N4 H4 109(10) C10 C5 C12 118.9(9) C10 C5 C15 121.1(9) C12 C5 C15 120.1(9) C16 C6 H6 119.8 C16 C6 C18 120.4(10) C18 C6 H6 119.8 C19 N7 C21 124.9(9) C19 N7 C22 112.9(9) C22 N7 C21 122.2(9) C1 C8 H8 120.5 C1 C8 C12 118.9(9) C12 C8 H8 120.5 N4 C9 H9 109.7 N4 C9 C11 114.0(8) N4 C9 C22 110.0(8) C11 C9 H9 109.7 C11 C9 C22 103.7(9) C22 C9 H9 109.7 C5 C10 H10 119.6 C5 C10 C14 120.8(9) C14 C10 H10 119.6 C9 C11 H11A 110.7 C9 C11 H11B 110.7 H11A C11 H11B 108.8 C19 C11 C9 105.2(8) C19 C11 H11A 110.7 C19 C11 H11B 110.7 C5 C12 C8 120.8(9) C5 C12 H12 119.6 C8 C12 H12 119.6 C17 C13 C18 119.6(9) C17 C13 C21 120.1(9) C18 C13 C21 120.2(9) C1 C14 C10 117.9(9) C1 C14 H14 121.1 C10 C14 H14 121.1 N4 C15 C5 110.8(8) N4 C15 H15A 109.5 N4 C15 H15B 109.5 C5 C15 H15A 109.5 C5 C15 H15B 109.5 H15A C15 H15B 108.1 C6 C16 H16 120.2 C6 C16 C20 119.7(9) C20 C16 H16 120.2 C13 C17 H17 119.7 C13 C17 C20 120.5(10) C20 C17 H17 119.7 C6 C18 H18 120.3 C13 C18 C6 119.5(9) C13 C18 H18 120.3 O2 C19 N7 123.9(10) O2 C19 C11 127.2(10) N7 C19 C11 108.7(9) C16 C20 C17 120.4(10) C16 C20 H20 119.8 C17 C20 H20 119.8 N7 C21 C13 112.3(8) N7 C21 H21A 109.1 N7 C21 H21B 109.1 C13 C21 H21A 109.1 C13 C21 H21B 109.1 H21A C21 H21B 107.9 O3 C22 N7 125.0(9) O3 C22 C9 127.7(11) N7 C22 C9 107.3(9) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Br1 C1 1.917(10) C1 C8 1.362(14) C1 C14 1.371(15) O2 C19 1.211(14) O3 C22 1.192(13) N4 C9 1.464(14) N4 C15 1.468(12) N4 H4 0.78(14) C5 C10 1.385(14) C5 C12 1.389(15) C5 C15 1.509(13) C6 H6 0.9500 C6 C16 1.380(16) C6 C18 1.405(14) N7 C19 1.358(14) N7 C21 1.481(12) N7 C22 1.413(16) C8 H8 0.9500 C8 C12 1.391(14) C9 H9 1.0000 C9 C11 1.521(14) C9 C22 1.528(14) C10 H10 0.9500 C10 C14 1.410(14) C11 H11A 0.9900 C11 H11B 0.9900 C11 C19 1.508(14) C12 H12 0.9500 C13 C17 1.382(14) C13 C18 1.393(15) C13 C21 1.507(14) C14 H14 0.9500 C15 H15A 0.9900 C15 H15B 0.9900 C16 H16 0.9500 C16 C20 1.383(17) C17 H17 0.9500 C17 C20 1.387(14) C18 H18 0.9500 C20 H20 0.9500 C21 H21A 0.9900 C21 H21B 0.9900 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 Br1 C1 C8 C12 -177.9(7) Br1 C1 C14 C10 177.5(7) C1 C8 C12 C5 -0.1(13) N4 C9 C11 C19 -134.5(8) N4 C9 C22 O3 -44.7(13) N4 C9 C22 N7 134.4(9) C5 C10 C14 C1 0.9(13) C6 C16 C20 C17 -0.5(15) C8 C1 C14 C10 -1.5(14) C9 N4 C15 C5 176.6(8) C9 C11 C19 O2 -171.5(9) C9 C11 C19 N7 13.2(10) C10 C5 C12 C8 -0.4(13) C10 C5 C15 N4 -82.0(11) C11 C9 C22 O3 -166.9(10) C11 C9 C22 N7 12.1(10) C12 C5 C10 C14 0.0(13) C12 C5 C15 N4 96.4(10) C13 C17 C20 C16 0.1(14) C14 C1 C8 C12 1.1(14) C15 N4 C9 C11 -68.1(11) C15 N4 C9 C22 176.0(8) C15 C5 C10 C14 178.4(8) C15 C5 C12 C8 -178.9(8) C16 C6 C18 C13 -0.1(15) C17 C13 C18 C6 -0.4(14) C17 C13 C21 N7 68.9(11) C18 C6 C16 C20 0.5(15) C18 C13 C17 C20 0.3(14) C18 C13 C21 N7 -112.3(10) C19 N7 C21 C13 70.7(12) C19 N7 C22 O3 174.8(9) C19 N7 C22 C9 -4.4(11) C21 N7 C19 O2 -1.4(15) C21 N7 C19 C11 174.1(8) C21 N7 C22 O3 -5.0(15) C21 N7 C22 C9 175.9(8) C21 C13 C17 C20 179.2(9) C21 C13 C18 C6 -179.2(9) C22 N7 C19 O2 178.8(9) C22 N7 C19 C11 -5.6(11) C22 N7 C21 C13 -109.5(10) C22 C9 C11 C19 -14.9(9)