#------------------------------------------------------------------------------ #$Date: 2021-11-21 01:12:20 +0200 (Sun, 21 Nov 2021) $ #$Revision: 270790 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/56/53/1565339.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_1565339 loop_ _publ_author_name 'Shen, Chong' 'Cheng, Xiang' 'Wei, Liang' 'Wang, Ruo-Qing' 'Wang, Chun-Jiang' _publ_section_title ; Stereodivergent Synthesis via Iridium-Catalyzed Asymmetric Double Allylic Alkylation of Cyanoacetate ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D1SC06115A _journal_year 2021 _chemical_absolute_configuration ad _chemical_formula_moiety 'C29 H28 Br N O2' _chemical_formula_sum 'C29 H28 Br N O2' _chemical_formula_weight 502.43 _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 geom _atom_sites_solution_primary dual _audit_creation_date 2021-01-15 _audit_creation_method ; Olex2 1.3 (compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226) ; _audit_update_record ; 2021-07-14 deposited with the CCDC. 2021-11-19 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.53030(10) _cell_length_b 8.69550(10) _cell_length_c 39.2876(3) _cell_measurement_reflns_used 15907 _cell_measurement_temperature 100.01(10) _cell_measurement_theta_max 73.5460 _cell_measurement_theta_min 4.5010 _cell_volume 2572.54(5) _computing_cell_refinement 'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.39.28b (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 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 100.01(10) _diffrn_detector 'CCD plate' _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.986 _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 -70.00 -11.00 0.50 0.50 -- 0.00 -19.00-180.00 118 2 \w -22.00 21.00 0.50 0.50 -- 0.00 57.00-150.00 86 3 \w 29.00 60.00 0.50 0.50 -- 0.00 57.00-150.00 62 4 \w -33.00 30.00 0.50 0.50 -- 0.00 -82.00 30.00 126 5 \w -33.00 31.00 0.50 0.50 -- 0.00 -82.00 120.00 128 6 \w -3.00 28.00 0.50 0.50 -- 0.00 -77.00-120.00 62 7 \w 56.00 116.00 0.50 0.50 -- 94.60 -82.00 90.00 120 8 \w 136.00 183.00 0.50 0.50 -- 94.60 30.00 -60.00 94 9 \w 5.00 118.00 0.50 0.50 -- 94.60 -61.00 90.00 226 10 \w 92.00 127.00 0.50 0.50 -- 94.60 30.00 -60.00 70 11 \w 40.00 116.00 0.50 0.50 -- 94.60 -82.00-120.00 152 12 \w 81.00 184.00 0.50 0.50 -- 94.60 77.00-150.00 206 13 \w 33.00 79.00 0.50 0.50 -- 94.60 -82.00 -90.00 92 14 \w 19.00 116.00 0.50 0.50 -- 94.60 -15.00-180.00 194 15 \w 71.00 142.00 0.50 0.50 -- 94.60 61.00-120.00 142 16 \w 85.00 110.00 0.50 0.50 -- 94.60 -45.00 30.00 50 17 \w 6.00 49.00 0.50 0.50 -- 94.60 -45.00 30.00 86 18 \w 76.00 182.00 0.50 0.50 -- 94.60 15.00 0.00 212 19 \w 71.00 157.00 0.50 0.50 -- 94.60 15.00 90.00 172 20 \w 94.00 120.00 0.50 0.50 -- 94.60 82.00-180.00 52 21 \w 98.00 124.00 0.50 0.50 -- 94.60 82.00 -90.00 52 22 \w 15.00 91.00 0.50 0.50 -- 94.60 -30.00 150.00 152 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB AFC12 (RINC): Kappa single' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0668474000 _diffrn_orient_matrix_UB_12 0.1120738000 _diffrn_orient_matrix_UB_13 -0.0275460000 _diffrn_orient_matrix_UB_21 -0.0631331000 _diffrn_orient_matrix_UB_22 0.1117904000 _diffrn_orient_matrix_UB_23 0.0279044000 _diffrn_orient_matrix_UB_31 0.1827430000 _diffrn_orient_matrix_UB_32 0.0795849000 _diffrn_orient_matrix_UB_33 -0.0004335000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0390 _diffrn_reflns_av_unetI/netI 0.0249 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.986 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 48 _diffrn_reflns_limit_l_min -47 _diffrn_reflns_number 26604 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.977 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 73.997 _diffrn_reflns_theta_min 4.502 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 2.364 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.80504 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.297 _exptl_crystal_description block _exptl_crystal_F_000 1040 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.257 _refine_diff_density_min -0.331 _refine_diff_density_rms 0.040 _refine_ls_abs_structure_details ; Flack x determined using 2035 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.026(6) _refine_ls_extinction_coef 0.00046(13) _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 1.056 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 302 _refine_ls_number_reflns 5128 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.056 _refine_ls_R_factor_all 0.0286 _refine_ls_R_factor_gt 0.0279 _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^)+(0.0350P)^2^+0.8187P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0727 _refine_ls_wR_factor_ref 0.0731 _reflns_Friedel_coverage 0.714 _reflns_Friedel_fraction_full 1.000 _reflns_Friedel_fraction_max 0.966 _reflns_number_gt 5020 _reflns_number_total 5128 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1sc06115a2.cif _cod_data_source_block 20210115_sc-14-148a _cod_database_code 1565339 _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 0.798 _shelx_estimated_absorpt_t_min 0.649 _reflns_odcompleteness_completeness 99.93 _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: C007(H007), C00D(H00D) 2.b Aromatic/amide H refined with riding coordinates: C008(H008), C00B(H00B), C00C(H00C), C00E(H00E), C00F(H00F), C00G(H00G), C00P(H00P), C00Q(H00Q), C00S(H00S), C00U(H00W), C00V(H00X), C00W(H00Y), C00X(H00Z) 2.c X=CH2 refined with riding coordinates: C00M(H00M,H00N), C00R(H00O,H00R) 2.d Idealised Me refined as rotating group: C00K(H00A,H00H,H00I), C00L(H00J,H00K,H00L), C00T(H00T,H00U,H00V) ; _shelx_res_file ; TITL 20210115_sc-14-148a_a.res in P2(1)2(1)2(1) 20210115_sc-14-148a.res created by SHELXL-2018/3 at 17:19:34 on 15-Jan-2021 REM Old TITL 20210115_SC-14-148A in P2(1)2(1)2(1) REM SHELXT solution in P2(1)2(1)2(1) REM R1 0.124, Rweak 0.052, Alpha 0.002, Orientation as input REM Flack x = 0.062 ( 0.007 ) from Parsons' quotients REM Formula found by SHELXT: C27 N O4 Br CELL 1.54184 7.5303 8.6955 39.2876 90 90 90 ZERR 4 0.0001 0.0001 0.0003 0 0 0 LATT -1 SYMM 0.5-X,-Y,0.5+Z SYMM -X,0.5+Y,0.5-Z SYMM 0.5+X,0.5-Y,-Z SFAC C H Br N O UNIT 116 112 4 4 8 L.S. 4 0 0 PLAN 6 SIZE 0.1 0.15 0.2 CONF BOND $H list 4 fmap 2 53 MORE -1 ACTA REM REM REM WGHT 0.035000 0.818700 EXTI 0.000457 FVAR 0.56251 BR01 3 0.075919 0.824548 0.213135 11.00000 0.06289 0.05553 = 0.04741 0.00515 -0.02840 -0.00522 O002 5 0.338302 0.597305 0.368662 11.00000 0.02286 0.01574 = 0.03169 -0.00006 0.00495 0.00016 O003 5 0.631549 0.545735 0.363426 11.00000 0.02747 0.02316 = 0.03716 -0.00516 0.00248 0.00525 N004 4 0.241915 0.964552 0.375805 11.00000 0.02875 0.02327 = 0.03527 -0.00076 0.00399 0.00170 C005 1 0.508582 0.633139 0.365855 11.00000 0.02615 0.01858 = 0.02192 -0.00049 0.00259 0.00076 C006 1 0.483027 0.854370 0.302748 11.00000 0.02233 0.02553 = 0.02181 -0.00100 0.00478 -0.00162 C007 1 0.616527 0.867274 0.331806 11.00000 0.02348 0.02411 = 0.02563 0.00011 0.00379 -0.00291 AFIX 13 H007 2 0.641381 0.977102 0.334745 11.00000 -1.20000 AFIX 0 C008 1 0.405356 0.986251 0.289268 11.00000 0.02886 0.02519 = 0.02790 0.00063 0.00508 -0.00211 AFIX 43 H008 2 0.435354 1.081645 0.298296 11.00000 -1.20000 AFIX 0 C009 1 0.365513 0.890628 0.371593 11.00000 0.02475 0.01795 = 0.02611 0.00105 0.00164 -0.00123 C00A 1 0.536181 0.808680 0.366583 11.00000 0.02192 0.01818 = 0.02686 -0.00091 0.00385 0.00054 C00B 1 0.284256 0.978898 0.262690 11.00000 0.03374 0.03026 = 0.03114 0.00747 0.00160 0.00239 AFIX 43 H00B 2 0.233209 1.067889 0.253934 11.00000 -1.20000 AFIX 0 C00C 1 0.436334 0.712446 0.288727 11.00000 0.02805 0.02577 = 0.02782 -0.00083 0.00180 0.00104 AFIX 43 H00C 2 0.487466 0.623071 0.297270 11.00000 -1.20000 AFIX 0 C00D 1 0.664111 0.845852 0.397194 11.00000 0.02623 0.02202 = 0.02619 -0.00166 0.00175 0.00159 AFIX 13 H00D 2 0.784520 0.816772 0.390254 11.00000 -1.20000 AFIX 0 C00E 1 0.665836 1.015644 0.404895 11.00000 0.02861 0.02368 = 0.02957 -0.00269 0.00017 0.00027 AFIX 43 H00E 2 0.562573 1.058935 0.413658 11.00000 -1.20000 AFIX 0 C00F 1 0.314675 0.702590 0.262208 11.00000 0.03239 0.02707 = 0.03021 -0.00371 0.00212 -0.00338 AFIX 43 H00F 2 0.283245 0.607592 0.253154 11.00000 -1.20000 AFIX 0 C00G 1 0.790088 0.792093 0.322564 11.00000 0.02403 0.04032 = 0.02774 0.00076 0.00381 0.00077 AFIX 43 H00G 2 0.790022 0.687118 0.318035 11.00000 -1.20000 AFIX 0 C00H 1 0.617844 0.752402 0.428898 11.00000 0.03900 0.02095 = 0.02447 -0.00516 -0.00180 0.00196 C00I 1 0.241331 0.836452 0.249552 11.00000 0.03188 0.03900 = 0.02771 0.00431 -0.00048 -0.00229 C00J 1 0.281337 0.433769 0.371376 11.00000 0.03342 0.01512 = 0.03464 0.00134 0.00708 -0.00269 C00K 1 0.358320 0.365625 0.403823 11.00000 0.06229 0.02333 = 0.03261 0.00393 0.00421 -0.00143 AFIX 137 H00A 2 0.485296 0.360559 0.401950 11.00000 -1.50000 H00H 2 0.311588 0.264020 0.407159 11.00000 -1.50000 H00I 2 0.326679 0.429276 0.422845 11.00000 -1.50000 AFIX 0 C00L 1 0.335519 0.344805 0.339909 11.00000 0.04072 0.02475 = 0.03573 -0.00602 0.00323 -0.00623 AFIX 137 H00J 2 0.297337 0.399341 0.319963 11.00000 -1.50000 H00K 2 0.281225 0.244934 0.340329 11.00000 -1.50000 H00L 2 0.462344 0.333743 0.339487 11.00000 -1.50000 AFIX 0 C00M 1 0.802595 1.106936 0.400130 11.00000 0.03587 0.02959 = 0.04445 -0.00504 0.00568 -0.00575 AFIX 93 H00M 2 0.908061 1.067650 0.391406 11.00000 -1.20000 H00N 2 0.793944 1.210852 0.405479 11.00000 -1.20000 AFIX 0 C00N 1 0.536258 0.578208 0.487481 11.00000 0.05192 0.02888 = 0.02626 -0.00499 0.00176 -0.00019 C00O 1 0.698805 0.554184 0.470108 11.00000 0.05256 0.02778 = 0.02776 -0.00382 -0.00180 0.00950 C00P 1 0.455444 0.773617 0.446360 11.00000 0.03499 0.03346 = 0.02971 0.00000 0.00428 0.00459 AFIX 43 H00P 2 0.374385 0.846157 0.438539 11.00000 -1.20000 AFIX 0 C00Q 1 0.734638 0.644588 0.440490 11.00000 0.04077 0.03256 = 0.02728 -0.00306 0.00144 0.00967 AFIX 43 H00Q 2 0.840594 0.629430 0.428801 11.00000 -1.20000 AFIX 0 C00R 1 0.942205 0.866726 0.320530 11.00000 0.02710 0.05672 = 0.03760 0.00178 0.00379 -0.00237 AFIX 93 H00O 2 0.946193 0.971761 0.324926 11.00000 -1.20000 H00R 2 1.045473 0.814315 0.314700 11.00000 -1.20000 AFIX 0 C00S 1 0.416298 0.687734 0.474860 11.00000 0.04195 0.04094 = 0.03000 -0.00305 0.00614 0.00296 AFIX 43 H00S 2 0.308483 0.702616 0.485926 11.00000 -1.20000 AFIX 0 C00T 1 0.080925 0.448857 0.373291 11.00000 0.03427 0.03041 = 0.06797 -0.00359 0.01394 -0.00910 AFIX 137 H00T 2 0.048941 0.502769 0.393714 11.00000 -1.50000 H00U 2 0.028184 0.348350 0.373508 11.00000 -1.50000 H00V 2 0.038800 0.505001 0.353862 11.00000 -1.50000 AFIX 0 C00U 1 0.622886 0.391870 0.529321 11.00000 0.07705 0.04130 = 0.02497 0.00670 -0.00174 -0.00423 AFIX 43 H00W 2 0.600593 0.339448 0.549507 11.00000 -1.20000 AFIX 0 C00V 1 0.503613 0.492076 0.517821 11.00000 0.06326 0.04352 = 0.02838 -0.00338 0.00539 -0.00278 AFIX 43 H00X 2 0.397892 0.506216 0.529650 11.00000 -1.20000 AFIX 0 C00W 1 0.820030 0.444335 0.482598 11.00000 0.06795 0.04456 = 0.03614 0.00144 0.00272 0.02534 AFIX 43 H00Y 2 0.926006 0.426907 0.471071 11.00000 -1.20000 AFIX 0 C00X 1 0.782875 0.363264 0.511534 11.00000 0.08916 0.04365 = 0.03722 0.00460 -0.00609 0.02111 AFIX 43 H00Z 2 0.862323 0.289692 0.519490 11.00000 -1.20000 AFIX 0 HKLF 4 REM 20210115_sc-14-148a_a.res in P2(1)2(1)2(1) REM wR2 = 0.0731, GooF = S = 1.056, Restrained GooF = 1.056 for all data REM R1 = 0.0279 for 5020 Fo > 4sig(Fo) and 0.0286 for all 5128 data REM 302 parameters refined using 0 restraints END WGHT 0.0350 0.8187 REM Highest difference peak 0.257, deepest hole -0.331, 1-sigma level 0.040 Q1 1 0.8629 0.6811 0.4379 11.00000 0.05 0.26 Q2 1 0.8537 0.5732 0.4612 11.00000 0.05 0.20 Q3 1 0.3625 0.4840 0.5202 11.00000 0.05 0.20 Q4 1 0.1750 0.8331 0.2432 11.00000 0.05 0.20 Q5 1 0.5452 0.7139 0.4406 11.00000 0.05 0.19 Q6 1 0.6637 0.9318 0.4006 11.00000 0.05 0.19 ; _shelx_res_checksum 56114 _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 1.934 _oxdiff_exptl_absorpt_empirical_full_min 0.695 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -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 Br01 Br 0.07592(5) 0.82455(4) 0.21313(2) 0.05528(13) Uani 1 1 d . . . . . O002 O 0.3383(2) 0.59731(18) 0.36866(4) 0.0234(3) Uani 1 1 d . . . . . O003 O 0.6315(2) 0.54574(19) 0.36343(5) 0.0293(4) Uani 1 1 d . . . . . N004 N 0.2419(3) 0.9646(2) 0.37581(6) 0.0291(5) Uani 1 1 d . . . . . C005 C 0.5086(3) 0.6331(2) 0.36586(6) 0.0222(5) Uani 1 1 d . . . . . C006 C 0.4830(3) 0.8544(3) 0.30275(6) 0.0232(5) Uani 1 1 d . . . . . C007 C 0.6165(3) 0.8673(3) 0.33181(6) 0.0244(5) Uani 1 1 d . . . . . H007 H 0.641381 0.977102 0.334745 0.029 Uiso 1 1 calc R U . . . C008 C 0.4054(3) 0.9863(3) 0.28927(6) 0.0273(5) Uani 1 1 d . . . . . H008 H 0.435354 1.081645 0.298296 0.033 Uiso 1 1 calc R U . . . C009 C 0.3655(3) 0.8906(3) 0.37159(6) 0.0229(5) Uani 1 1 d . . . . . C00A C 0.5362(3) 0.8087(3) 0.36658(6) 0.0223(5) Uani 1 1 d . . . . . C00B C 0.2843(4) 0.9789(3) 0.26269(7) 0.0317(6) Uani 1 1 d . . . . . H00B H 0.233209 1.067889 0.253934 0.038 Uiso 1 1 calc R U . . . C00C C 0.4363(3) 0.7124(3) 0.28873(6) 0.0272(5) Uani 1 1 d . . . . . H00C H 0.487466 0.623071 0.297270 0.033 Uiso 1 1 calc R U . . . C00D C 0.6641(3) 0.8459(3) 0.39719(6) 0.0248(5) Uani 1 1 d . . . . . H00D H 0.784520 0.816772 0.390254 0.030 Uiso 1 1 calc R U . . . C00E C 0.6658(4) 1.0156(3) 0.40489(6) 0.0273(5) Uani 1 1 d . . . . . H00E H 0.562573 1.058935 0.413658 0.033 Uiso 1 1 calc R U . . . C00F C 0.3147(4) 0.7026(3) 0.26221(6) 0.0299(5) Uani 1 1 d . . . . . H00F H 0.283245 0.607592 0.253154 0.036 Uiso 1 1 calc R U . . . C00G C 0.7901(3) 0.7921(3) 0.32256(6) 0.0307(5) Uani 1 1 d . . . . . H00G H 0.790022 0.687118 0.318035 0.037 Uiso 1 1 calc R U . . . C00H C 0.6178(4) 0.7524(3) 0.42890(6) 0.0281(5) Uani 1 1 d . . . . . C00I C 0.2413(4) 0.8365(3) 0.24955(6) 0.0329(6) Uani 1 1 d . . . . . C00J C 0.2813(4) 0.4338(3) 0.37138(7) 0.0277(5) Uani 1 1 d . . . . . C00K C 0.3583(5) 0.3656(3) 0.40382(7) 0.0394(7) Uani 1 1 d . . . . . H00A H 0.485296 0.360559 0.401950 0.059 Uiso 1 1 calc R U . . . H00H H 0.311588 0.264020 0.407159 0.059 Uiso 1 1 calc R U . . . H00I H 0.326679 0.429276 0.422845 0.059 Uiso 1 1 calc R U . . . C00L C 0.3355(4) 0.3448(3) 0.33991(7) 0.0337(6) Uani 1 1 d . . . . . H00J H 0.297337 0.399341 0.319963 0.051 Uiso 1 1 calc R U . . . H00K H 0.281225 0.244934 0.340329 0.051 Uiso 1 1 calc R U . . . H00L H 0.462344 0.333743 0.339487 0.051 Uiso 1 1 calc R U . . . C00M C 0.8026(4) 1.1069(3) 0.40013(7) 0.0366(6) Uani 1 1 d . . . . . H00M H 0.908061 1.067650 0.391406 0.044 Uiso 1 1 calc R U . . . H00N H 0.793944 1.210852 0.405479 0.044 Uiso 1 1 calc R U . . . C00N C 0.5363(4) 0.5782(3) 0.48748(7) 0.0357(6) Uani 1 1 d . . . . . C00O C 0.6988(4) 0.5542(3) 0.47011(7) 0.0360(6) Uani 1 1 d . . . . . C00P C 0.4554(4) 0.7736(3) 0.44636(7) 0.0327(6) Uani 1 1 d . . . . . H00P H 0.374385 0.846157 0.438539 0.039 Uiso 1 1 calc R U . . . C00Q C 0.7346(4) 0.6446(3) 0.44049(7) 0.0335(6) Uani 1 1 d . . . . . H00Q H 0.840594 0.629430 0.428801 0.040 Uiso 1 1 calc R U . . . C00R C 0.9422(4) 0.8667(4) 0.32053(7) 0.0405(7) Uani 1 1 d . . . . . H00O H 0.946193 0.971761 0.324926 0.049 Uiso 1 1 calc R U . . . H00R H 1.045473 0.814315 0.314700 0.049 Uiso 1 1 calc R U . . . C00S C 0.4163(4) 0.6877(3) 0.47486(6) 0.0376(6) Uani 1 1 d . . . . . H00S H 0.308483 0.702616 0.485926 0.045 Uiso 1 1 calc R U . . . C00T C 0.0809(4) 0.4489(3) 0.37329(9) 0.0442(7) Uani 1 1 d . . . . . H00T H 0.048941 0.502769 0.393714 0.066 Uiso 1 1 calc R U . . . H00U H 0.028184 0.348350 0.373508 0.066 Uiso 1 1 calc R U . . . H00V H 0.038800 0.505001 0.353862 0.066 Uiso 1 1 calc R U . . . C00U C 0.6229(5) 0.3919(4) 0.52932(7) 0.0478(8) Uani 1 1 d . . . . . H00W H 0.600593 0.339448 0.549507 0.057 Uiso 1 1 calc R U . . . C00V C 0.5036(5) 0.4921(4) 0.51782(7) 0.0451(7) Uani 1 1 d . . . . . H00X H 0.397892 0.506216 0.529650 0.054 Uiso 1 1 calc R U . . . C00W C 0.8200(5) 0.4443(4) 0.48260(8) 0.0496(8) Uani 1 1 d . . . . . H00Y H 0.926006 0.426907 0.471071 0.059 Uiso 1 1 calc R U . . . C00X C 0.7829(6) 0.3633(4) 0.51153(8) 0.0567(10) Uani 1 1 d . . . . . H00Z H 0.862323 0.289692 0.519490 0.068 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 Br01 0.0629(2) 0.0555(2) 0.04741(19) 0.00515(16) -0.02840(17) -0.00522(17) O002 0.0229(8) 0.0157(7) 0.0317(8) -0.0001(6) 0.0049(7) 0.0002(6) O003 0.0275(9) 0.0232(8) 0.0372(9) -0.0052(7) 0.0025(7) 0.0053(7) N004 0.0288(11) 0.0233(10) 0.0353(11) -0.0008(8) 0.0040(9) 0.0017(9) C005 0.0262(12) 0.0186(11) 0.0219(10) -0.0005(8) 0.0026(9) 0.0008(9) C006 0.0223(11) 0.0255(11) 0.0218(10) -0.0010(9) 0.0048(9) -0.0016(9) C007 0.0235(12) 0.0241(11) 0.0256(11) 0.0001(8) 0.0038(9) -0.0029(9) C008 0.0289(12) 0.0252(11) 0.0279(11) 0.0006(9) 0.0051(11) -0.0021(9) C009 0.0247(12) 0.0180(10) 0.0261(11) 0.0011(9) 0.0016(9) -0.0012(9) C00A 0.0219(11) 0.0182(10) 0.0269(10) -0.0009(9) 0.0038(9) 0.0005(9) C00B 0.0337(14) 0.0303(13) 0.0311(12) 0.0075(10) 0.0016(11) 0.0024(11) C00C 0.0281(12) 0.0258(11) 0.0278(11) -0.0008(9) 0.0018(11) 0.0010(9) C00D 0.0262(12) 0.0220(11) 0.0262(11) -0.0017(9) 0.0018(9) 0.0016(9) C00E 0.0286(13) 0.0237(11) 0.0296(12) -0.0027(9) 0.0002(10) 0.0003(10) C00F 0.0324(14) 0.0271(12) 0.0302(12) -0.0037(10) 0.0021(11) -0.0034(10) C00G 0.0240(12) 0.0403(14) 0.0277(11) 0.0008(11) 0.0038(10) 0.0008(11) C00H 0.0390(15) 0.0210(11) 0.0245(11) -0.0052(9) -0.0018(10) 0.0020(10) C00I 0.0319(14) 0.0390(14) 0.0277(11) 0.0043(11) -0.0005(10) -0.0023(12) C00J 0.0334(14) 0.0151(10) 0.0346(13) 0.0013(9) 0.0071(11) -0.0027(9) C00K 0.062(2) 0.0233(12) 0.0326(13) 0.0039(10) 0.0042(13) -0.0014(12) C00L 0.0407(15) 0.0248(12) 0.0357(13) -0.0060(11) 0.0032(11) -0.0062(11) C00M 0.0359(15) 0.0296(12) 0.0444(15) -0.0050(12) 0.0057(12) -0.0058(11) C00N 0.0519(18) 0.0289(13) 0.0263(12) -0.0050(10) 0.0018(12) -0.0002(12) C00O 0.0526(17) 0.0278(12) 0.0278(12) -0.0038(10) -0.0018(12) 0.0095(12) C00P 0.0350(15) 0.0335(13) 0.0297(12) 0.0000(10) 0.0043(11) 0.0046(11) C00Q 0.0408(15) 0.0326(13) 0.0273(12) -0.0031(10) 0.0014(11) 0.0097(11) C00R 0.0271(14) 0.0567(18) 0.0376(14) 0.0018(13) 0.0038(12) -0.0024(13) C00S 0.0420(15) 0.0409(14) 0.0300(12) -0.0031(11) 0.0061(11) 0.0030(14) C00T 0.0343(15) 0.0304(13) 0.068(2) -0.0036(13) 0.0139(15) -0.0091(13) C00U 0.077(2) 0.0413(15) 0.0250(13) 0.0067(12) -0.0017(14) -0.0042(16) C00V 0.063(2) 0.0435(16) 0.0284(13) -0.0034(12) 0.0054(13) -0.0028(15) C00W 0.068(2) 0.0446(17) 0.0361(15) 0.0014(13) 0.0027(15) 0.0253(17) C00X 0.089(3) 0.0437(18) 0.0372(16) 0.0046(13) -0.0061(17) 0.0211(18) 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 C005 O002 C00J 120.64(18) . . ? O002 C005 C00A 111.23(19) . . ? O003 C005 O002 127.2(2) . . ? O003 C005 C00A 121.6(2) . . ? C008 C006 C007 120.1(2) . . ? C008 C006 C00C 118.2(2) . . ? C00C C006 C007 121.7(2) . . ? C006 C007 H007 106.6 . . ? C006 C007 C00A 111.80(19) . . ? C00A C007 H007 106.6 . . ? C00G C007 C006 111.08(19) . . ? C00G C007 H007 106.6 . . ? C00G C007 C00A 113.65(19) . . ? C006 C008 H008 119.2 . . ? C00B C008 C006 121.6(2) . . ? C00B C008 H008 119.2 . . ? N004 C009 C00A 174.4(2) . . ? C005 C00A C007 110.82(18) . . ? C005 C00A C00D 107.46(18) . . ? C009 C00A C005 111.20(19) . . ? C009 C00A C007 106.98(18) . . ? C009 C00A C00D 109.29(18) . . ? C00D C00A C007 111.12(18) . . ? C008 C00B H00B 120.8 . . ? C00I C00B C008 118.5(2) . . ? C00I C00B H00B 120.8 . . ? C006 C00C H00C 119.5 . . ? C00F C00C C006 121.1(2) . . ? C00F C00C H00C 119.5 . . ? C00A C00D H00D 107.5 . . ? C00E C00D C00A 111.08(19) . . ? C00E C00D H00D 107.5 . . ? C00E C00D C00H 111.06(19) . . ? C00H C00D C00A 112.0(2) . . ? C00H C00D H00D 107.5 . . ? C00D C00E H00E 117.6 . . ? C00M C00E C00D 124.8(3) . . ? C00M C00E H00E 117.6 . . ? C00C C00F H00F 120.6 . . ? C00I C00F C00C 118.8(2) . . ? C00I C00F H00F 120.6 . . ? C007 C00G H00G 118.2 . . ? C00R C00G C007 123.7(3) . . ? C00R C00G H00G 118.2 . . ? C00P C00H C00D 121.6(2) . . ? C00Q C00H C00D 119.4(2) . . ? C00Q C00H C00P 119.0(2) . . ? C00B C00I Br01 119.0(2) . . ? C00B C00I C00F 121.9(2) . . ? C00F C00I Br01 119.2(2) . . ? O002 C00J C00K 108.8(2) . . ? O002 C00J C00L 110.6(2) . . ? O002 C00J C00T 101.98(19) . . ? C00L C00J C00K 112.5(2) . . ? C00L C00J C00T 110.7(2) . . ? C00T C00J C00K 111.8(2) . . ? C00J C00K H00A 109.5 . . ? C00J C00K H00H 109.5 . . ? C00J C00K H00I 109.5 . . ? H00A C00K H00H 109.5 . . ? H00A C00K H00I 109.5 . . ? H00H C00K H00I 109.5 . . ? C00J C00L H00J 109.5 . . ? C00J C00L H00K 109.5 . . ? C00J C00L H00L 109.5 . . ? H00J C00L H00K 109.5 . . ? H00J C00L H00L 109.5 . . ? H00K C00L H00L 109.5 . . ? C00E C00M H00M 120.0 . . ? C00E C00M H00N 120.0 . . ? H00M C00M H00N 120.0 . . ? C00O C00N C00V 118.2(3) . . ? C00S C00N C00O 119.1(2) . . ? C00S C00N C00V 122.7(3) . . ? C00N C00O C00Q 118.3(2) . . ? C00W C00O C00N 119.5(3) . . ? C00W C00O C00Q 122.3(3) . . ? C00H C00P H00P 119.7 . . ? C00S C00P C00H 120.6(3) . . ? C00S C00P H00P 119.7 . . ? C00H C00Q C00O 121.9(3) . . ? C00H C00Q H00Q 119.1 . . ? C00O C00Q H00Q 119.1 . . ? C00G C00R H00O 120.0 . . ? C00G C00R H00R 120.0 . . ? H00O C00R H00R 120.0 . . ? C00N C00S H00S 119.4 . . ? C00P C00S C00N 121.2(3) . . ? C00P C00S H00S 119.4 . . ? C00J C00T H00T 109.5 . . ? C00J C00T H00U 109.5 . . ? C00J C00T H00V 109.5 . . ? H00T C00T H00U 109.5 . . ? H00T C00T H00V 109.5 . . ? H00U C00T H00V 109.5 . . ? C00V C00U H00W 119.3 . . ? C00V C00U C00X 121.5(3) . . ? C00X C00U H00W 119.3 . . ? C00N C00V H00X 119.7 . . ? C00U C00V C00N 120.7(3) . . ? C00U C00V H00X 119.7 . . ? C00O C00W H00Y 119.8 . . ? C00X C00W C00O 120.4(3) . . ? C00X C00W H00Y 119.8 . . ? C00U C00X H00Z 120.2 . . ? C00W C00X C00U 119.6(3) . . ? C00W C00X H00Z 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 Br01 C00I 1.900(3) . ? O002 C005 1.324(3) . ? O002 C00J 1.489(3) . ? O003 C005 1.202(3) . ? N004 C009 1.143(3) . ? C005 C00A 1.541(3) . ? C006 C007 1.525(3) . ? C006 C008 1.392(3) . ? C006 C00C 1.396(3) . ? C007 H007 0.9800 . ? C007 C00A 1.579(3) . ? C007 C00G 1.506(3) . ? C008 H008 0.9300 . ? C008 C00B 1.388(4) . ? C009 C00A 1.483(3) . ? C00A C00D 1.574(3) . ? C00B H00B 0.9300 . ? C00B C00I 1.380(4) . ? C00C H00C 0.9300 . ? C00C C00F 1.390(4) . ? C00D H00D 0.9800 . ? C00D C00E 1.507(3) . ? C00D C00H 1.527(3) . ? C00E H00E 0.9300 . ? C00E C00M 1.314(4) . ? C00F H00F 0.9300 . ? C00F C00I 1.381(4) . ? C00G H00G 0.9300 . ? C00G C00R 1.319(4) . ? C00H C00P 1.414(4) . ? C00H C00Q 1.364(4) . ? C00J C00K 1.521(4) . ? C00J C00L 1.514(4) . ? C00J C00T 1.517(4) . ? C00K H00A 0.9600 . ? C00K H00H 0.9600 . ? C00K H00I 0.9600 . ? C00L H00J 0.9600 . ? C00L H00K 0.9600 . ? C00L H00L 0.9600 . ? C00M H00M 0.9300 . ? C00M H00N 0.9300 . ? C00N C00O 1.417(4) . ? C00N C00S 1.403(4) . ? C00N C00V 1.429(4) . ? C00O C00Q 1.430(4) . ? C00O C00W 1.409(4) . ? C00P H00P 0.9300 . ? C00P C00S 1.378(4) . ? C00Q H00Q 0.9300 . ? C00R H00O 0.9300 . ? C00R H00R 0.9300 . ? C00S H00S 0.9300 . ? C00T H00T 0.9600 . ? C00T H00U 0.9600 . ? C00T H00V 0.9600 . ? C00U H00W 0.9300 . ? C00U C00V 1.330(5) . ? C00U C00X 1.415(5) . ? C00V H00X 0.9300 . ? C00W H00Y 0.9300 . ? C00W C00X 1.367(5) . ? C00X H00Z 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 O002 C005 C00A C007 -116.6(2) . . . . ? O002 C005 C00A C009 2.2(3) . . . . ? O002 C005 C00A C00D 121.8(2) . . . . ? O003 C005 C00A C007 64.2(3) . . . . ? O003 C005 C00A C009 -176.9(2) . . . . ? O003 C005 C00A C00D -57.4(3) . . . . ? C005 O002 C00J C00K 62.8(3) . . . . ? C005 O002 C00J C00L -61.2(3) . . . . ? C005 O002 C00J C00T -178.9(2) . . . . ? C005 C00A C00D C00E -167.1(2) . . . . ? C005 C00A C00D C00H -42.2(2) . . . . ? C006 C007 C00A C005 69.2(2) . . . . ? C006 C007 C00A C009 -52.1(2) . . . . ? C006 C007 C00A C00D -171.36(19) . . . . ? C006 C007 C00G C00R 117.9(3) . . . . ? C006 C008 C00B C00I -0.1(4) . . . . ? C006 C00C C00F C00I 0.7(4) . . . . ? C007 C006 C008 C00B 179.6(2) . . . . ? C007 C006 C00C C00F -179.9(2) . . . . ? C007 C00A C00D C00E 71.6(2) . . . . ? C007 C00A C00D C00H -163.63(19) . . . . ? C008 C006 C007 C00A 108.0(2) . . . . ? C008 C006 C007 C00G -123.9(2) . . . . ? C008 C006 C00C C00F -0.5(3) . . . . ? C008 C00B C00I Br01 -179.94(19) . . . . ? C008 C00B C00I C00F 0.3(4) . . . . ? C009 C00A C00D C00E -46.3(3) . . . . ? C009 C00A C00D C00H 78.5(2) . . . . ? C00A C007 C00G C00R -114.9(3) . . . . ? C00A C00D C00E C00M -112.2(3) . . . . ? C00A C00D C00H C00P -65.5(3) . . . . ? C00A C00D C00H C00Q 113.7(3) . . . . ? C00C C006 C007 C00A -72.6(3) . . . . ? C00C C006 C007 C00G 55.5(3) . . . . ? C00C C006 C008 C00B 0.2(4) . . . . ? C00C C00F C00I Br01 179.64(18) . . . . ? C00C C00F C00I C00B -0.6(4) . . . . ? C00D C00H C00P C00S 179.8(2) . . . . ? C00D C00H C00Q C00O 179.7(2) . . . . ? C00E C00D C00H C00P 59.3(3) . . . . ? C00E C00D C00H C00Q -121.5(3) . . . . ? C00G C007 C00A C005 -57.5(3) . . . . ? C00G C007 C00A C009 -178.9(2) . . . . ? C00G C007 C00A C00D 61.9(3) . . . . ? C00H C00D C00E C00M 122.5(3) . . . . ? C00H C00P C00S C00N 0.5(4) . . . . ? C00J O002 C005 O003 4.0(4) . . . . ? C00J O002 C005 C00A -175.05(18) . . . . ? C00N C00O C00Q C00H 0.4(4) . . . . ? C00N C00O C00W C00X -1.1(5) . . . . ? C00O C00N C00S C00P -1.2(4) . . . . ? C00O C00N C00V C00U -0.1(4) . . . . ? C00O C00W C00X C00U -1.0(5) . . . . ? C00P C00H C00Q C00O -1.0(4) . . . . ? C00Q C00H C00P C00S 0.6(4) . . . . ? C00Q C00O C00W C00X 178.2(3) . . . . ? C00S C00N C00O C00Q 0.7(4) . . . . ? C00S C00N C00O C00W -180.0(3) . . . . ? C00S C00N C00V C00U -178.4(3) . . . . ? C00V C00N C00O C00Q -177.6(3) . . . . ? C00V C00N C00O C00W 1.7(4) . . . . ? C00V C00N C00S C00P 177.1(3) . . . . ? C00V C00U C00X C00W 2.7(5) . . . . ? C00W C00O C00Q C00H -178.9(3) . . . . ? C00X C00U C00V C00N -2.0(5) . . . . ?