#------------------------------------------------------------------------------ #$Date: 2024-12-06 22:01:13 +0200 (Fri, 06 Dec 2024) $ #$Revision: 296613 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/94/7249409.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_7249409 loop_ _publ_author_name 'Wu, Yingtao' 'Guan, Xin' 'Jiao, Kehan' 'Zhao, Huaqiu' 'Li, Mingrui' 'Sun, Jiaqiong' 'Zheng, Guangfan' 'Zhang, Qian' _publ_section_title ; Synthesis of axially chiral thiourea by NHC-catalyzed desymmetrizative amidation ; _journal_issue 21 _journal_name_full 'Green Chemistry' _journal_page_first 10940 _journal_page_last 10949 _journal_paper_doi 10.1039/D4GC03113J _journal_volume 26 _journal_year 2024 _chemical_formula_moiety '2(C27 H19 Br N2 O2 S)' _chemical_formula_sum 'C54 H38 Br2 N4 O4 S2' _chemical_formula_weight 1030.82 _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_creation_date 2022-12-02 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2022-12-02 deposited with the CCDC. 2024-09-17 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 9.2241(8) _cell_length_b 10.3990(10) _cell_length_c 25.056(2) _cell_measurement_reflns_used 9213 _cell_measurement_temperature 287(2) _cell_measurement_theta_max 64.417 _cell_measurement_theta_min 3.528 _cell_volume 2403.4(4) _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 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_temperature 287.16 _diffrn_measured_fraction_theta_full 0.976 _diffrn_measured_fraction_theta_max 0.976 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0313 _diffrn_reflns_av_unetI/netI 0.0394 _diffrn_reflns_Laue_measured_fraction_full 0.976 _diffrn_reflns_Laue_measured_fraction_max 0.976 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_number 9599 _diffrn_reflns_point_group_measured_fraction_full 0.959 _diffrn_reflns_point_group_measured_fraction_max 0.959 _diffrn_reflns_theta_full 63.862 _diffrn_reflns_theta_max 63.862 _diffrn_reflns_theta_min 3.528 _exptl_absorpt_coefficient_mu 3.356 _exptl_absorpt_correction_type none _exptl_crystal_colour 'clear whiteish colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier whiteish _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.424 _exptl_crystal_description block _exptl_crystal_F_000 1048 _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _refine_diff_density_max 0.578 _refine_diff_density_min -1.029 _refine_diff_density_rms 0.078 _refine_ls_abs_structure_details ; Flack x determined using 1409 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.092(10) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 298 _refine_ls_number_reflns 3816 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.071 _refine_ls_R_factor_all 0.0464 _refine_ls_R_factor_gt 0.0436 _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^)+(0.0604P)^2^+1.7858P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1121 _refine_ls_wR_factor_ref 0.1150 _reflns_Friedel_coverage 0.707 _reflns_Friedel_fraction_full 0.935 _reflns_Friedel_fraction_max 0.935 _reflns_number_gt 3609 _reflns_number_total 3816 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4gc03113j2.cif _cod_data_source_block 2 _cod_depositor_comments 'Adding full bibliography for 7249409.cif.' _cod_database_code 7249409 _shelx_shelxl_version_number 2016/4 _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 0.488 _shelx_estimated_absorpt_t_min 0.433 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All N(H) groups 2.a Riding coordinates: N003(H003), N006(H006) 2.b Aromatic/amide H refined with riding coordinates: C00E(H00E), C00H(H00H), C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X) ; _shelx_res_file ; TITL 2 P 21 21 21 R = 0.05 New: P212121 2.res created by SHELXL-2016/4 at 14:45:44 on 02-Dec-2022 CELL 1.54178 9.2241 10.399 25.056 90 90 90 ZERR 2 0.0008 0.001 0.002 0 0 0 LATT -1 SYMM 0.5-X,-Y,0.5+Z SYMM 0.5+X,0.5-Y,-Z SYMM -X,0.5+Y,0.5-Z SFAC C H Br N O S UNIT 108 76 4 8 8 4 L.S. 5 PLAN -20 SIZE 0.25 0.25 0.3 TEMP 14 BOND $H CONF fmap 2 acta OMIT 2 0 8 REM REM REM WGHT 0.060400 1.785800 FVAR 0.53011 S1 6 0.002591 0.192278 0.131797 11.00000 0.03838 0.03333 = 0.04391 -0.00630 0.00324 -0.00831 BR01 3 0.486754 -0.141610 -0.005817 11.00000 0.04072 0.09373 = 0.07747 0.00673 0.01552 0.00794 O004 5 -0.243826 -0.168897 0.085558 11.00000 0.04938 0.04310 = 0.05547 -0.02065 0.02445 -0.01860 O005 5 -0.711961 -0.359997 0.266783 11.00000 0.04718 0.07595 = 0.05948 0.03239 0.02204 0.00313 N003 4 -0.199811 0.015374 0.132439 11.00000 0.03208 0.03336 = 0.03588 -0.01051 0.01362 -0.00602 AFIX 3 H003 2 -0.232611 0.060994 0.158419 11.00000 -1.20000 AFIX 0 N006 4 -0.025349 -0.010059 0.067560 11.00000 0.03969 0.03854 = 0.04651 -0.01488 0.02063 -0.01321 AFIX 3 H006 2 -0.068589 -0.081449 0.060740 11.00000 -1.20000 AFIX 0 C007 1 -0.438483 -0.217904 0.182321 11.00000 0.02411 0.03723 = 0.02488 -0.00659 0.00272 -0.00376 C008 1 -0.573781 -0.232851 0.207115 11.00000 0.02930 0.03829 = 0.02773 -0.00116 0.00200 -0.00357 C009 1 -0.279284 -0.092738 0.120046 11.00000 0.03098 0.03209 = 0.03224 -0.00463 0.00576 -0.00762 C00A 1 -0.417640 -0.107243 0.151003 11.00000 0.02750 0.03129 = 0.03153 -0.00829 0.00855 -0.00675 C00B 1 -0.073563 0.059836 0.108324 11.00000 0.02722 0.03079 = 0.03036 -0.00002 0.00340 -0.00139 C00C 1 0.325104 -0.028675 -0.002327 11.00000 0.03483 0.05297 = 0.03330 -0.00606 0.00879 -0.00446 C00D 1 -0.326728 -0.437066 0.167281 11.00000 0.02920 0.03938 = 0.03463 0.00303 0.00097 0.00315 C00E 1 0.210482 -0.059553 0.031474 11.00000 0.03554 0.04206 = 0.03319 -0.00042 0.00834 -0.00937 AFIX 43 H00E 2 0.212054 -0.134801 0.051524 11.00000 -1.20000 AFIX 0 C00F 1 0.094654 0.023793 0.034579 11.00000 0.03359 0.03914 = 0.03489 -0.00690 0.01008 -0.01114 C00G 1 -0.317584 -0.312460 0.188334 11.00000 0.02630 0.04331 = 0.02959 -0.00030 0.00172 0.00177 C00H 1 -0.520707 -0.413669 0.097234 11.00000 0.03577 0.03629 = 0.04030 -0.00502 -0.00542 -0.00547 AFIX 43 H00H 2 -0.477681 -0.337561 0.085876 11.00000 -1.20000 AFIX 0 C00I 1 -0.458654 -0.482730 0.138674 11.00000 0.03183 0.03481 = 0.04505 -0.00387 0.00259 0.00133 C00J 1 -0.527030 -0.017727 0.144814 11.00000 0.03904 0.03640 = 0.04398 0.00172 0.00734 -0.00172 AFIX 43 H00J 2 -0.510158 0.055679 0.124542 11.00000 -1.20000 AFIX 0 C00K 1 -0.600051 -0.342390 0.243148 11.00000 0.03735 0.05365 = 0.03715 0.00992 0.00897 -0.00252 AFIX 43 H00K 2 -0.525595 -0.401581 0.247929 11.00000 -1.20000 AFIX 0 C00L 1 -0.661300 -0.035570 0.168302 11.00000 0.03202 0.04459 = 0.04955 -0.00130 0.00477 0.00716 AFIX 43 H00L 2 -0.735397 0.023712 0.162990 11.00000 -1.20000 AFIX 0 C00M 1 -0.683539 -0.143016 0.199813 11.00000 0.02779 0.04564 = 0.04019 -0.00525 0.00729 -0.00430 AFIX 43 H00M 2 -0.772844 -0.155250 0.216276 11.00000 -1.20000 AFIX 0 C00N 1 -0.084942 -0.479152 0.199723 11.00000 0.03631 0.08009 = 0.05554 0.00845 -0.00533 0.01481 AFIX 43 H00N 2 -0.006448 -0.534772 0.202850 11.00000 -1.20000 AFIX 0 C00O 1 0.324239 0.079603 -0.032458 11.00000 0.05029 0.05572 = 0.04289 0.00317 0.01854 -0.01808 AFIX 43 H00O 2 0.401857 0.098550 -0.054804 11.00000 -1.20000 AFIX 0 C00P 1 -0.193201 -0.274506 0.215212 11.00000 0.03193 0.06439 = 0.04397 -0.00299 -0.00447 -0.00736 AFIX 43 H00P 2 -0.187967 -0.191970 0.229374 11.00000 -1.20000 AFIX 0 C00Q 1 -0.077228 -0.356856 0.221316 11.00000 0.02930 0.09387 = 0.05241 0.00150 -0.01095 -0.00221 AFIX 43 H00Q 2 0.005157 -0.330541 0.239716 11.00000 -1.20000 AFIX 0 C00R 1 -0.208271 -0.518644 0.173672 11.00000 0.04009 0.05214 = 0.05387 0.00431 -0.00374 0.01276 AFIX 43 H00R 2 -0.212714 -0.601700 0.160007 11.00000 -1.20000 AFIX 0 C00S 1 0.092271 0.135033 0.004205 11.00000 0.04875 0.04534 = 0.05037 -0.00264 0.01400 -0.00237 AFIX 43 H00S 2 0.014229 0.191365 0.006580 11.00000 -1.20000 AFIX 0 C00T 1 0.206146 0.161671 -0.029516 11.00000 0.07113 0.05065 = 0.04831 0.01070 0.01662 -0.01649 AFIX 43 H00T 2 0.203826 0.235391 -0.050512 11.00000 -1.20000 AFIX 0 C00U 1 -0.645273 -0.456381 0.072683 11.00000 0.04302 0.05560 = 0.05776 -0.00511 -0.01500 0.00062 AFIX 43 H00U 2 -0.686129 -0.408977 0.045036 11.00000 -1.20000 AFIX 0 C00V 1 -0.523233 -0.597703 0.152950 11.00000 0.05331 0.04492 = 0.09152 0.01696 -0.01102 -0.01106 AFIX 43 H00V 2 -0.480874 -0.647449 0.179563 11.00000 -1.20000 AFIX 0 C00W 1 -0.647681 -0.640424 0.129055 11.00000 0.06162 0.05325 = 0.12574 0.02201 -0.01796 -0.01978 AFIX 43 H00W 2 -0.689750 -0.717296 0.140008 11.00000 -1.20000 AFIX 0 C00X 1 -0.709966 -0.570343 0.089216 11.00000 0.04202 0.06707 = 0.10378 -0.00567 -0.01550 -0.01961 AFIX 43 H00X 2 -0.795170 -0.598579 0.073203 11.00000 -1.20000 AFIX 0 HKLF 4 REM 2 P 21 21 21 R = 0.05 New: P212121 REM R1 = 0.0436 for 3609 Fo > 4sig(Fo) and 0.0464 for all 3816 data REM 298 parameters refined using 0 restraints END WGHT 0.0580 1.8635 REM Highest difference peak 0.578, deepest hole -1.029, 1-sigma level 0.078 Q1 1 0.5080 -0.0547 0.0096 11.00000 0.05 0.58 Q2 1 0.1822 0.2956 -0.0515 11.00000 0.05 0.31 Q3 1 0.4382 -0.1224 -0.0382 11.00000 0.05 0.23 Q4 1 -0.6478 -0.3077 0.0842 11.00000 0.05 0.21 Q5 1 -0.5838 -0.2624 0.1072 11.00000 0.05 0.20 Q6 1 0.5380 -0.2490 0.0346 11.00000 0.05 0.19 Q7 1 -0.4794 0.1172 0.0958 11.00000 0.05 0.18 Q8 1 -0.5003 -0.0892 0.0939 11.00000 0.05 0.18 Q9 1 -0.6512 -0.3532 0.1805 11.00000 0.05 0.17 Q10 1 0.5844 -0.1222 -0.0434 11.00000 0.05 0.17 Q11 1 -0.4989 -0.3444 0.2574 11.00000 0.05 0.17 Q12 1 -0.5919 -0.7474 0.0833 11.00000 0.05 0.17 Q13 1 -0.3158 -0.1185 0.0836 11.00000 0.05 0.17 Q14 1 -0.1254 -0.0191 0.0399 11.00000 0.05 0.17 Q15 1 0.7391 0.5843 0.0798 11.00000 0.05 0.17 Q16 1 -0.6744 -0.8145 0.0583 11.00000 0.05 0.16 Q17 1 -0.5626 -0.2981 0.2193 11.00000 0.05 0.16 Q18 1 0.0936 0.8214 0.1048 11.00000 0.05 0.16 Q19 1 -0.0175 -0.5856 0.2403 11.00000 0.05 0.16 Q20 1 -0.1958 -0.0632 0.2494 11.00000 0.05 0.16 ; _shelx_res_checksum 53306 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -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 S1 S 0.00259(15) 0.19228(11) 0.13180(5) 0.0385(3) Uani 1 1 d . . . . . Br01 Br 0.48675(7) -0.14161(8) -0.00582(3) 0.0706(3) Uani 1 1 d . . . . . O004 O -0.2438(4) -0.1689(4) 0.08556(16) 0.0493(10) Uani 1 1 d . . . . . O005 O -0.7120(4) -0.3600(5) 0.26678(17) 0.0609(12) Uani 1 1 d . . . . . N003 N -0.1998(4) 0.0154(4) 0.13244(16) 0.0338(9) Uani 1 1 d . . . . . H003 H -0.232611 0.060994 0.158419 0.041 Uiso 1 1 d R . . . . N006 N -0.0253(5) -0.0101(4) 0.06756(16) 0.0416(11) Uani 1 1 d . . . . . H006 H -0.068589 -0.081449 0.060740 0.050 Uiso 1 1 d R . . . . C007 C -0.4385(5) -0.2179(5) 0.18232(17) 0.0287(10) Uani 1 1 d . . . . . C008 C -0.5738(5) -0.2329(5) 0.20712(18) 0.0318(11) Uani 1 1 d . . . . . C009 C -0.2793(5) -0.0927(5) 0.12005(19) 0.0318(11) Uani 1 1 d . . . . . C00A C -0.4176(5) -0.1072(5) 0.15100(18) 0.0301(11) Uani 1 1 d . . . . . C00B C -0.0736(5) 0.0598(5) 0.10832(18) 0.0295(10) Uani 1 1 d . . . . . C00C C 0.3251(5) -0.0287(5) -0.0023(2) 0.0404(12) Uani 1 1 d . . . . . C00D C -0.3267(5) -0.4371(5) 0.1673(2) 0.0344(11) Uani 1 1 d . . . . . C00E C 0.2105(6) -0.0596(5) 0.0315(2) 0.0369(12) Uani 1 1 d . . . . . H00E H 0.212054 -0.134801 0.051524 0.044 Uiso 1 1 calc R . . . . C00F C 0.0947(5) 0.0238(5) 0.0346(2) 0.0359(12) Uani 1 1 d . . . . . C00G C -0.3176(5) -0.3125(5) 0.18833(19) 0.0331(11) Uani 1 1 d . . . . . C00H C -0.5207(6) -0.4137(5) 0.09723(19) 0.0375(11) Uani 1 1 d . . . . . H00H H -0.477681 -0.337561 0.085876 0.045 Uiso 1 1 calc R . . . . C00I C -0.4587(5) -0.4827(5) 0.1387(2) 0.0372(12) Uani 1 1 d . . . . . C00J C -0.5270(6) -0.0177(5) 0.1448(2) 0.0398(12) Uani 1 1 d . . . . . H00J H -0.510158 0.055679 0.124542 0.048 Uiso 1 1 calc R . . . . C00K C -0.6001(6) -0.3424(6) 0.2431(2) 0.0427(13) Uani 1 1 d . . . . . H00K H -0.525595 -0.401581 0.247929 0.051 Uiso 1 1 calc R . . . . C00L C -0.6613(6) -0.0356(5) 0.1683(2) 0.0421(12) Uani 1 1 d . . . . . H00L H -0.735397 0.023712 0.162990 0.050 Uiso 1 1 calc R . . . . C00M C -0.6835(5) -0.1430(5) 0.1998(2) 0.0379(11) Uani 1 1 d . . . . . H00M H -0.772844 -0.155250 0.216276 0.045 Uiso 1 1 calc R . . . . C00N C -0.0849(7) -0.4792(7) 0.1997(2) 0.0573(17) Uani 1 1 d . . . . . H00N H -0.006448 -0.534772 0.202850 0.069 Uiso 1 1 calc R . . . . C00O C 0.3242(7) 0.0796(6) -0.0325(2) 0.0496(15) Uani 1 1 d . . . . . H00O H 0.401857 0.098550 -0.054804 0.060 Uiso 1 1 calc R . . . . C00P C -0.1932(6) -0.2745(6) 0.2152(2) 0.0468(14) Uani 1 1 d . . . . . H00P H -0.187967 -0.191970 0.229374 0.056 Uiso 1 1 calc R . . . . C00Q C -0.0772(6) -0.3569(8) 0.2213(2) 0.0585(17) Uani 1 1 d . . . . . H00Q H 0.005157 -0.330541 0.239716 0.070 Uiso 1 1 calc R . . . . C00R C -0.2083(6) -0.5186(6) 0.1737(2) 0.0487(14) Uani 1 1 d . . . . . H00R H -0.212714 -0.601700 0.160007 0.058 Uiso 1 1 calc R . . . . C00S C 0.0923(6) 0.1350(6) 0.0042(2) 0.0482(13) Uani 1 1 d . . . . . H00S H 0.014229 0.191365 0.006580 0.058 Uiso 1 1 calc R . . . . C00T C 0.2061(7) 0.1617(6) -0.0295(2) 0.0567(16) Uani 1 1 d . . . . . H00T H 0.203826 0.235391 -0.050512 0.068 Uiso 1 1 calc R . . . . C00U C -0.6453(7) -0.4564(6) 0.0727(2) 0.0521(15) Uani 1 1 d . . . . . H00U H -0.686129 -0.408977 0.045036 0.063 Uiso 1 1 calc R . . . . C00V C -0.5232(8) -0.5977(6) 0.1530(3) 0.0633(18) Uani 1 1 d . . . . . H00V H -0.480874 -0.647449 0.179563 0.076 Uiso 1 1 calc R . . . . C00W C -0.6477(8) -0.6404(8) 0.1291(4) 0.080(2) Uani 1 1 d . . . . . H00W H -0.689750 -0.717296 0.140008 0.096 Uiso 1 1 calc R . . . . C00X C -0.7100(7) -0.5703(7) 0.0892(3) 0.071(2) Uani 1 1 d . . . . . H00X H -0.795170 -0.598579 0.073203 0.085 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 S1 0.0384(6) 0.0333(6) 0.0439(6) -0.0063(5) 0.0032(6) -0.0083(6) Br01 0.0407(4) 0.0937(6) 0.0775(5) 0.0067(4) 0.0155(3) 0.0079(3) O004 0.049(2) 0.043(2) 0.055(2) -0.0207(19) 0.0245(18) -0.0186(17) O005 0.047(2) 0.076(3) 0.059(2) 0.032(2) 0.022(2) 0.003(2) N003 0.032(2) 0.033(2) 0.036(2) -0.0105(18) 0.0136(18) -0.0060(18) N006 0.040(3) 0.039(2) 0.047(2) -0.0149(18) 0.021(2) -0.013(2) C007 0.024(2) 0.037(3) 0.025(2) -0.0066(19) 0.0027(18) -0.0038(19) C008 0.029(2) 0.038(3) 0.028(2) -0.001(2) 0.0020(19) -0.004(2) C009 0.031(2) 0.032(3) 0.032(2) -0.005(2) 0.006(2) -0.008(2) C00A 0.027(2) 0.031(3) 0.032(2) -0.008(2) 0.009(2) -0.007(2) C00B 0.027(2) 0.031(3) 0.030(2) 0.000(2) 0.0034(19) -0.001(2) C00C 0.035(2) 0.053(3) 0.033(2) -0.006(2) 0.009(2) -0.004(2) C00D 0.029(3) 0.039(3) 0.035(2) 0.003(2) 0.001(2) 0.003(2) C00E 0.036(3) 0.042(3) 0.033(2) 0.000(2) 0.008(2) -0.009(2) C00F 0.034(3) 0.039(3) 0.035(2) -0.007(2) 0.010(2) -0.011(2) C00G 0.026(2) 0.043(3) 0.030(2) 0.000(2) 0.0017(19) 0.002(2) C00H 0.036(3) 0.036(3) 0.040(3) -0.005(2) -0.005(2) -0.005(2) C00I 0.032(3) 0.035(3) 0.045(3) -0.004(2) 0.003(2) 0.001(2) C00J 0.039(3) 0.036(3) 0.044(3) 0.002(2) 0.007(2) -0.002(2) C00K 0.037(3) 0.054(3) 0.037(3) 0.010(2) 0.009(2) -0.003(3) C00L 0.032(3) 0.045(3) 0.050(3) -0.001(3) 0.005(2) 0.007(2) C00M 0.028(2) 0.046(3) 0.040(3) -0.005(2) 0.007(2) -0.004(2) C00N 0.036(3) 0.080(5) 0.056(4) 0.008(3) -0.005(3) 0.015(3) C00O 0.050(3) 0.056(4) 0.043(3) 0.003(3) 0.019(3) -0.018(3) C00P 0.032(3) 0.064(4) 0.044(3) -0.003(3) -0.004(2) -0.007(3) C00Q 0.029(3) 0.094(5) 0.052(3) 0.001(4) -0.011(2) -0.002(3) C00R 0.040(3) 0.052(3) 0.054(3) 0.004(3) -0.004(3) 0.013(3) C00S 0.049(3) 0.045(3) 0.050(3) -0.003(3) 0.014(3) -0.002(2) C00T 0.071(4) 0.051(4) 0.048(3) 0.011(3) 0.017(3) -0.016(3) C00U 0.043(3) 0.056(4) 0.058(4) -0.005(3) -0.015(3) 0.001(3) C00V 0.053(4) 0.045(4) 0.092(5) 0.017(3) -0.011(4) -0.011(3) C00W 0.062(4) 0.053(4) 0.126(7) 0.022(4) -0.018(4) -0.020(4) C00X 0.042(4) 0.067(5) 0.104(6) -0.006(4) -0.015(4) -0.020(3) 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' S S 0.3331 0.5567 '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 C009 N003 H003 115.7 . . ? C009 N003 C00B 128.2(4) . . ? C00B N003 H003 116.1 . . ? C00B N006 H006 118.0 . . ? C00B N006 C00F 124.7(4) . . ? C00F N006 H006 117.3 . . ? C008 C007 C00A 117.4(4) . . ? C008 C007 C00G 123.1(4) . . ? C00A C007 C00G 119.5(4) . . ? C007 C008 C00K 120.2(5) . . ? C00M C008 C007 121.0(5) . . ? C00M C008 C00K 118.7(4) . . ? O004 C009 N003 123.2(4) . . ? O004 C009 C00A 122.0(4) . . ? N003 C009 C00A 114.7(4) . . ? C007 C00A C009 119.1(4) . . ? C00J C00A C007 120.9(4) . . ? C00J C00A C009 119.7(4) . . ? N003 C00B S1 118.5(3) . . ? N006 C00B S1 125.9(4) . . ? N006 C00B N003 115.6(4) . . ? C00E C00C Br01 118.8(4) . . ? C00O C00C Br01 119.5(4) . . ? C00O C00C C00E 121.7(5) . . ? C00G C00D C00I 121.7(4) . . ? C00R C00D C00G 118.2(5) . . ? C00R C00D C00I 120.1(5) . . ? C00C C00E H00E 120.7 . . ? C00F C00E C00C 118.6(5) . . ? C00F C00E H00E 120.7 . . ? C00E C00F N006 118.7(5) . . ? C00E C00F C00S 120.4(5) . . ? C00S C00F N006 120.8(5) . . ? C00D C00G C007 121.7(4) . . ? C00P C00G C007 118.6(5) . . ? C00P C00G C00D 119.7(5) . . ? C00I C00H H00H 119.6 . . ? C00U C00H H00H 119.6 . . ? C00U C00H C00I 120.8(5) . . ? C00H C00I C00D 122.2(5) . . ? C00V C00I C00D 120.2(5) . . ? C00V C00I C00H 117.6(5) . . ? C00A C00J H00J 119.5 . . ? C00A C00J C00L 121.0(5) . . ? C00L C00J H00J 119.5 . . ? O005 C00K C008 124.0(5) . . ? O005 C00K H00K 118.0 . . ? C008 C00K H00K 118.0 . . ? C00J C00L H00L 120.5 . . ? C00M C00L C00J 118.9(5) . . ? C00M C00L H00L 120.5 . . ? C008 C00M H00M 119.7 . . ? C00L C00M C008 120.7(5) . . ? C00L C00M H00M 119.7 . . ? C00Q C00N H00N 119.9 . . ? C00R C00N H00N 119.9 . . ? C00R C00N C00Q 120.2(6) . . ? C00C C00O H00O 120.4 . . ? C00C C00O C00T 119.1(5) . . ? C00T C00O H00O 120.4 . . ? C00G C00P H00P 119.4 . . ? C00Q C00P C00G 121.2(6) . . ? C00Q C00P H00P 119.4 . . ? C00N C00Q H00Q 120.4 . . ? C00P C00Q C00N 119.2(5) . . ? C00P C00Q H00Q 120.4 . . ? C00D C00R H00R 119.3 . . ? C00N C00R C00D 121.5(6) . . ? C00N C00R H00R 119.3 . . ? C00F C00S H00S 120.2 . . ? C00T C00S C00F 119.6(6) . . ? C00T C00S H00S 120.2 . . ? C00O C00T H00T 119.7 . . ? C00S C00T C00O 120.6(6) . . ? C00S C00T H00T 119.7 . . ? C00H C00U H00U 120.0 . . ? C00H C00U C00X 120.0(6) . . ? C00X C00U H00U 120.0 . . ? C00I C00V H00V 119.0 . . ? C00W C00V C00I 121.9(6) . . ? C00W C00V H00V 119.0 . . ? C00V C00W H00W 120.0 . . ? C00X C00W C00V 120.0(7) . . ? C00X C00W H00W 120.0 . . ? C00U C00X H00X 120.2 . . ? C00W C00X C00U 119.6(6) . . ? C00W C00X H00X 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 S1 C00B 1.654(5) . ? Br01 C00C 1.900(5) . ? O004 C009 1.217(6) . ? O005 C00K 1.204(6) . ? N003 H003 0.8604 . ? N003 C009 1.378(6) . ? N003 C00B 1.391(6) . ? N006 H006 0.8599 . ? N006 C00B 1.330(6) . ? N006 C00F 1.426(6) . ? C007 C008 1.403(7) . ? C007 C00A 1.406(7) . ? C007 C00G 1.494(7) . ? C008 C00K 1.474(7) . ? C008 C00M 1.390(7) . ? C009 C00A 1.501(6) . ? C00A C00J 1.382(7) . ? C00C C00E 1.392(7) . ? C00C C00O 1.356(8) . ? C00D C00G 1.402(8) . ? C00D C00I 1.490(7) . ? C00D C00R 1.393(7) . ? C00E H00E 0.9300 . ? C00E C00F 1.378(7) . ? C00F C00S 1.385(8) . ? C00G C00P 1.388(7) . ? C00H H00H 0.9300 . ? C00H C00I 1.386(7) . ? C00H C00U 1.377(7) . ? C00I C00V 1.383(8) . ? C00J H00J 0.9300 . ? C00J C00L 1.384(8) . ? C00K H00K 0.9300 . ? C00L H00L 0.9300 . ? C00L C00M 1.383(8) . ? C00M H00M 0.9300 . ? C00N H00N 0.9300 . ? C00N C00Q 1.384(10) . ? C00N C00R 1.374(9) . ? C00O H00O 0.9300 . ? C00O C00T 1.386(9) . ? C00P H00P 0.9300 . ? C00P C00Q 1.379(9) . ? C00Q H00Q 0.9300 . ? C00R H00R 0.9300 . ? C00S H00S 0.9300 . ? C00S C00T 1.376(8) . ? C00T H00T 0.9300 . ? C00U H00U 0.9300 . ? C00U C00X 1.390(10) . ? C00V H00V 0.9300 . ? C00V C00W 1.369(10) . ? C00W H00W 0.9300 . ? C00W C00X 1.363(11) . ? C00X H00X 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 Br01 C00C C00E C00F 178.9(4) . . . . ? Br01 C00C C00O C00T -179.8(4) . . . . ? O004 C009 C00A C007 61.1(7) . . . . ? O004 C009 C00A C00J -113.4(6) . . . . ? N003 C009 C00A C007 -121.2(5) . . . . ? N003 C009 C00A C00J 64.2(6) . . . . ? N006 C00F C00S C00T -176.4(5) . . . . ? C007 C008 C00K O005 178.2(5) . . . . ? C007 C008 C00M C00L -0.8(8) . . . . ? C007 C00A C00J C00L -1.4(7) . . . . ? C007 C00G C00P C00Q -179.0(5) . . . . ? C008 C007 C00A C009 -174.9(4) . . . . ? C008 C007 C00A C00J -0.4(7) . . . . ? C008 C007 C00G C00D 67.2(6) . . . . ? C008 C007 C00G C00P -113.3(6) . . . . ? C009 N003 C00B S1 -178.9(4) . . . . ? C009 N003 C00B N006 1.3(7) . . . . ? C009 C00A C00J C00L 173.0(5) . . . . ? C00A C007 C008 C00K -176.2(4) . . . . ? C00A C007 C008 C00M 1.5(7) . . . . ? C00A C007 C00G C00D -113.6(5) . . . . ? C00A C007 C00G C00P 66.0(6) . . . . ? C00A C00J C00L C00M 2.1(8) . . . . ? C00B N003 C009 O004 2.5(8) . . . . ? C00B N003 C009 C00A -175.1(5) . . . . ? C00B N006 C00F C00E 121.2(6) . . . . ? C00B N006 C00F C00S -62.0(7) . . . . ? C00C C00E C00F N006 177.6(4) . . . . ? C00C C00E C00F C00S 0.7(8) . . . . ? C00C C00O C00T C00S 1.1(9) . . . . ? C00D C00G C00P C00Q 0.5(8) . . . . ? C00D C00I C00V C00W 177.4(7) . . . . ? C00E C00C C00O C00T 0.0(9) . . . . ? C00E C00F C00S C00T 0.4(8) . . . . ? C00F N006 C00B S1 -5.2(8) . . . . ? C00F N006 C00B N003 174.6(5) . . . . ? C00F C00S C00T C00O -1.4(9) . . . . ? C00G C007 C008 C00K 3.0(7) . . . . ? C00G C007 C008 C00M -179.2(4) . . . . ? C00G C007 C00A C009 5.8(6) . . . . ? C00G C007 C00A C00J -179.7(4) . . . . ? C00G C00D C00I C00H 51.2(7) . . . . ? C00G C00D C00I C00V -129.1(6) . . . . ? C00G C00D C00R C00N -0.2(8) . . . . ? C00G C00P C00Q C00N 0.6(9) . . . . ? C00H C00I C00V C00W -2.9(10) . . . . ? C00H C00U C00X C00W -1.3(11) . . . . ? C00I C00D C00G C007 -1.2(7) . . . . ? C00I C00D C00G C00P 179.3(5) . . . . ? C00I C00D C00R C00N 179.8(5) . . . . ? C00I C00H C00U C00X -0.3(9) . . . . ? C00I C00V C00W C00X 1.3(13) . . . . ? C00J C00L C00M C008 -1.1(8) . . . . ? C00K C008 C00M C00L 177.0(5) . . . . ? C00M C008 C00K O005 0.4(8) . . . . ? C00O C00C C00E C00F -0.9(8) . . . . ? C00Q C00N C00R C00D 1.3(10) . . . . ? C00R C00D C00G C007 178.8(5) . . . . ? C00R C00D C00G C00P -0.8(7) . . . . ? C00R C00D C00I C00H -128.8(6) . . . . ? C00R C00D C00I C00V 51.0(8) . . . . ? C00R C00N C00Q C00P -1.6(10) . . . . ? C00U C00H C00I C00D -177.9(5) . . . . ? C00U C00H C00I C00V 2.3(8) . . . . ? C00V C00W C00X C00U 0.8(13) . . . . ?