#------------------------------------------------------------------------------ #$Date: 2021-11-21 01:12:20 +0200 (Sun, 21 Nov 2021) $ #$Revision: 270790 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/56/53/1565338.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_1565338 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 'C25 H25 Br2 N O2' _chemical_formula_sum 'C25 H25 Br2 N O2' _chemical_formula_weight 531.28 _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2020-11-24 _audit_creation_method ; Olex2 1.3 (compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003) ; _audit_update_record ; 2021-07-14 deposited with the CCDC. 2021-11-19 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 112.4700(10) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 10.68950(10) _cell_length_b 11.14220(10) _cell_length_c 10.92190(10) _cell_measurement_reflns_used 23537 _cell_measurement_temperature 100.01(10) _cell_measurement_theta_max 73.4640 _cell_measurement_theta_min 3.9590 _cell_volume 1202.09(2) _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 1.000 _diffrn_measured_fraction_theta_max 0.996 _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 34.00 89.00 0.50 0.50 -- 0.00 32.00-142.00 110 2 \w -12.00 20.00 0.50 0.50 -- 0.00 32.00-142.00 64 3 \w 32.00 58.00 0.50 0.50 -- 94.60 -32.00 58.00 52 4 \w 107.00 146.00 0.50 0.50 -- 94.60 32.00-142.00 78 5 \w -54.00 -16.00 0.50 0.50 -- 0.00 -32.00 58.00 76 6 \w -12.00 13.00 0.50 0.50 -- 0.00 -32.00 58.00 50 7 \w 73.00 120.00 0.50 0.50 -- 32.00 72.00 -45.98 94 8 \w 6.00 47.00 0.50 0.50 -- 32.00 72.00 -45.98 82 9 \w 10.00 61.00 0.50 0.50 -- 36.00 72.00 170.83 102 10 \w 1.00 61.00 0.50 0.50 -- 44.00 -38.00 -16.74 120 11 \w -44.00 -3.00 0.50 0.50 -- 44.00 -38.00 -16.74 82 12 \w 29.00 54.00 0.50 0.50 -- 52.00 73.00-118.99 50 13 \w 25.00 83.00 0.50 0.50 -- 52.00 72.00 24.57 116 14 \w 32.00 79.00 0.50 0.50 -- 60.00 75.00 -69.87 94 15 \w 36.00 61.00 0.50 0.50 -- 64.00 74.00 -35.59 50 16 \w 37.00 73.00 0.50 0.50 -- 64.00 75.00 69.04 72 17 \w 36.00 67.00 0.50 0.50 -- 64.00 75.00 178.18 62 18 \w 41.00 75.00 0.50 0.50 -- 68.00 75.00-114.22 68 19 \w 40.00 65.00 0.50 0.50 -- 68.00 74.00 135.23 50 20 \w 40.00 77.00 0.50 0.50 -- 68.00 74.00 35.97 74 21 \w 41.00 69.00 0.50 0.50 -- 68.00 75.00 -19.38 56 22 \w 40.00 72.00 0.50 0.50 -- 68.00 75.00-151.53 64 23 \w 44.00 69.00 0.50 0.50 -- 72.00 75.00 89.21 50 24 \w 45.00 73.00 0.50 0.50 -- 72.00 75.00 105.88 56 25 \w 126.00 157.00 0.50 0.50 -- 72.00 74.00 -41.94 62 26 \w 46.00 71.00 0.50 0.50 -- 72.00 74.00 -41.94 50 27 \w 100.00 165.00 0.50 0.50 -- 76.00 75.00 1.94 130 28 \w 49.00 76.00 0.50 0.50 -- 76.00 75.00 1.94 54 29 \w 61.00 107.00 0.50 0.50 -- 84.00 67.00 158.60 92 30 \w 136.00 172.00 0.50 0.50 -- 94.60 61.00 120.00 72 31 \w 73.00 99.00 0.50 0.50 -- 94.60 -77.00 -90.00 52 32 \w 5.00 69.00 0.50 0.50 -- 94.60 -77.00 -90.00 128 33 \w 71.00 128.00 0.50 0.50 -- 94.60 61.00 120.00 114 34 \w 7.00 36.00 0.50 0.50 -- 94.60 -82.00 150.00 58 35 \w 5.00 39.00 0.50 0.50 -- 94.60 -82.00-150.00 68 36 \w 73.00 164.00 0.50 0.50 -- 94.60 58.00 -59.67 182 37 \w 67.00 183.00 0.50 0.50 -- 94.60 72.00-104.35 232 38 \w 98.00 126.00 0.50 0.50 -- 94.60 -82.00 0.00 56 39 \w 71.00 182.00 0.50 0.50 -- 94.60 61.00 60.00 222 40 \w 8.00 125.00 0.50 0.50 -- 94.60 -82.00 -30.00 234 41 \w 74.00 125.00 0.50 0.50 -- 94.60 -82.00 60.00 102 42 \w 72.00 115.00 0.50 0.50 -- 94.60 61.00 0.00 86 43 \w 63.00 109.00 0.50 0.50 -- 94.60 -61.00 150.00 92 44 \w 30.00 56.00 0.50 0.50 -- 94.60 -61.00 150.00 52 45 \w 71.00 169.00 0.50 0.50 -- 94.60 59.00-123.34 196 46 \w 127.00 152.00 0.50 0.50 -- 94.60 61.00 90.00 50 47 \w 74.00 112.00 0.50 0.50 -- 94.60 61.00 90.00 76 48 \w 78.00 154.00 0.50 0.50 -- 94.60 30.00 30.00 152 49 \w 71.00 168.00 0.50 0.50 -- 94.60 61.00-150.00 194 50 \w 42.00 68.00 0.50 0.50 -- 94.60 -82.00 60.00 52 51 \w 80.00 113.00 0.50 0.50 -- 94.60 77.00 -60.00 66 52 \w 5.00 94.00 0.50 0.50 -- 94.60 -82.00 0.00 178 53 \w 73.00 178.00 0.50 0.50 -- 94.60 61.00-180.00 210 54 \w 72.00 121.00 0.50 0.50 -- 94.60 56.00 151.60 98 55 \w 71.00 117.00 0.50 0.50 -- 94.60 61.00 30.00 92 56 \w 42.00 122.00 0.50 0.50 -- 94.60 -82.00 150.00 160 57 \w 93.00 120.00 0.50 0.50 -- 94.60 -82.00-150.00 54 58 \w 151.00 176.00 0.50 0.50 -- 94.60 61.00 0.00 50 ; _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 -0.1276797000 _diffrn_orient_matrix_UB_12 -0.0426494000 _diffrn_orient_matrix_UB_13 0.0205558000 _diffrn_orient_matrix_UB_21 -0.0880240000 _diffrn_orient_matrix_UB_22 0.0382976000 _diffrn_orient_matrix_UB_23 -0.1425905000 _diffrn_orient_matrix_UB_31 0.0165371000 _diffrn_orient_matrix_UB_32 -0.1258307000 _diffrn_orient_matrix_UB_33 -0.0503819000 _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 0.0288 _diffrn_reflns_av_unetI/netI 0.0140 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 26178 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.980 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 73.796 _diffrn_reflns_theta_min 4.381 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 4.433 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.50697 _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 1.468 _exptl_crystal_description block _exptl_crystal_F_000 536 _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.224 _refine_diff_density_min -0.497 _refine_diff_density_rms 0.056 _refine_ls_abs_structure_details ; Flack x determined using 2190 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.016(6) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 274 _refine_ls_number_reflns 4773 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.067 _refine_ls_R_factor_all 0.0193 _refine_ls_R_factor_gt 0.0192 _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^)+(0.0280P)^2^+0.5140P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0498 _refine_ls_wR_factor_ref 0.0498 _reflns_Friedel_coverage 0.868 _reflns_Friedel_fraction_full 0.994 _reflns_Friedel_fraction_max 0.963 _reflns_number_gt 4759 _reflns_number_total 4773 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1sc06115a2.cif _cod_data_source_block 20201124_sc-13-56a _cod_database_code 1565338 _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 0.666 _shelx_estimated_absorpt_t_min 0.350 _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: C00G(H00G), C00H(H00H) 2.b Aromatic/amide H refined with riding coordinates: C007(H007), C00C(H00C), C00D(H00D), C00I(H00I), C00J(H00J), C00M(H00M), C00R(H00U), C00S(H00V), C00T(H00W), C00U(H00X) 2.c X=CH2 refined with riding coordinates: C006(H00A,H00B), C00Q(H00S,H00T) 2.d Idealised Me refined as rotating group: C00N(H00E,H00F,H00K), C00O(H00L,H00N,H00O), C00P(H00P,H00Q,H00R) ; _shelx_res_file ; TITL 20201124_sc-13-56a_a.res in P2(1) 20201124_sc-13-56a.res created by SHELXL-2018/3 at 15:33:47 on 24-Nov-2020 REM Old TITL 20201124_SC-13-56A in P2(1) REM SHELXT solution in P2(1) REM R1 0.078, Rweak 0.039, Alpha 0.003, Orientation as input REM Flack x = 0.028 ( 0.006 ) from Parsons' quotients REM Formula found by SHELXT: C24 N O3 Br2 CELL 1.54184 10.6895 11.1422 10.9219 90 112.47 90 ZERR 2 0.0001 0.0001 0.0001 0 0.001 0 LATT -1 SYMM -X,0.5+Y,-Z SFAC C H Br N O UNIT 50 50 4 2 4 L.S. 4 0 0 PLAN 6 SIZE 0.1 0.15 0.3 CONF BOND $H list 4 fmap 2 53 MORE -1 ACTA REM REM REM WGHT 0.028000 0.514000 FVAR 0.59239 BR01 3 0.892601 0.856698 0.379612 11.00000 0.02359 0.03297 = 0.02963 0.00191 0.01153 -0.01077 BR02 3 -0.064644 0.143272 0.206182 11.00000 0.03448 0.02789 = 0.03671 -0.01058 0.01769 -0.01606 O003 5 0.414818 0.433571 0.139531 11.00000 0.02039 0.01649 = 0.01340 -0.00010 0.00818 0.00196 O004 5 0.421391 0.316844 0.312500 11.00000 0.02198 0.01512 = 0.01737 -0.00060 0.00869 0.00025 N005 4 0.359379 0.717612 0.169421 11.00000 0.01740 0.02240 = 0.02137 0.00304 0.00735 0.00188 C006 1 0.578268 0.499800 0.683645 11.00000 0.03666 0.02211 = 0.01839 0.00375 0.01070 0.00148 AFIX 93 H00A 2 0.573218 0.580056 0.704695 11.00000 -1.20000 H00B 2 0.596501 0.441258 0.748876 11.00000 -1.20000 AFIX 0 C007 1 0.108084 0.347249 0.271477 11.00000 0.01608 0.02088 = 0.01763 -0.00314 0.00902 -0.00380 AFIX 43 H007 2 0.157506 0.303349 0.346945 11.00000 -1.20000 AFIX 0 C008 1 0.376067 0.632505 0.233880 11.00000 0.01053 0.01514 = 0.01578 -0.00144 0.00431 0.00044 C009 1 -0.007230 0.298371 0.175336 11.00000 0.02126 0.02327 = 0.02420 -0.00774 0.01489 -0.00685 C00A 1 0.650996 0.576045 0.411788 11.00000 0.01148 0.01987 = 0.01231 0.00017 0.00259 0.00107 C00B 1 0.149200 0.462342 0.254152 11.00000 0.01269 0.02093 = 0.01742 -0.00200 0.00707 -0.00107 C00C 1 0.559589 0.469035 0.561402 11.00000 0.01727 0.01558 = 0.01833 0.00011 0.00496 -0.00110 AFIX 43 H00C 2 0.565031 0.388337 0.542253 11.00000 -1.20000 AFIX 0 C00D 1 0.236027 0.632377 0.415204 11.00000 0.01344 0.01994 = 0.02666 -0.00418 0.00930 -0.00262 AFIX 43 H00D 2 0.211349 0.697751 0.357969 11.00000 -1.20000 AFIX 0 C00E 1 0.419494 0.333896 0.049149 11.00000 0.02710 0.01923 = 0.01562 -0.00353 0.00982 0.00187 C00F 1 0.413489 0.412305 0.258771 11.00000 0.00981 0.01741 = 0.01422 -0.00123 0.00494 -0.00011 C00G 1 0.272433 0.516102 0.365647 11.00000 0.01311 0.01757 = 0.01521 -0.00066 0.00657 -0.00109 AFIX 13 H00G 2 0.298656 0.459227 0.439659 11.00000 -1.20000 AFIX 0 C00H 1 0.529544 0.560275 0.450722 11.00000 0.01208 0.01351 = 0.01395 -0.00065 0.00369 0.00021 AFIX 13 H00H 2 0.514000 0.637513 0.485462 11.00000 -1.20000 AFIX 0 C00I 1 0.701300 0.690640 0.407502 11.00000 0.01412 0.02021 = 0.01281 -0.00110 0.00419 0.00099 AFIX 43 H00I 2 0.660280 0.757863 0.426378 11.00000 -1.20000 AFIX 0 C00J 1 0.713361 0.477489 0.381299 11.00000 0.01592 0.02111 = 0.02644 -0.00394 0.00747 0.00080 AFIX 43 H00J 2 0.681065 0.400725 0.385481 11.00000 -1.20000 AFIX 0 C00K 1 0.814466 0.702548 0.374320 11.00000 0.01511 0.02815 = 0.01545 0.00071 0.00542 -0.00434 C00L 1 0.398066 0.530280 0.325233 11.00000 0.01171 0.01399 = 0.01422 0.00119 0.00505 -0.00005 C00M 1 -0.082056 0.360018 0.061114 11.00000 0.01665 0.03908 = 0.02083 -0.00836 0.00491 -0.00822 AFIX 43 H00M 2 -0.159098 0.326062 -0.002280 11.00000 -1.20000 AFIX 0 C00N 1 0.421886 0.404552 -0.069190 11.00000 0.03702 0.03112 = 0.01797 -0.00008 0.01409 0.00453 AFIX 137 H00E 2 0.342848 0.454471 -0.103506 11.00000 -1.50000 H00F 2 0.422787 0.349890 -0.136791 11.00000 -1.50000 H00K 2 0.501532 0.453863 -0.041919 11.00000 -1.50000 AFIX 0 C00O 1 0.548193 0.261430 0.111980 11.00000 0.03120 0.02412 = 0.02194 -0.00213 0.01393 0.00764 AFIX 137 H00L 2 0.624821 0.314421 0.140143 11.00000 -1.50000 H00N 2 0.555894 0.205378 0.048472 11.00000 -1.50000 H00O 2 0.545439 0.218557 0.187152 11.00000 -1.50000 AFIX 0 C00P 1 0.291072 0.260186 0.013443 11.00000 0.03314 0.03026 = 0.02142 -0.01113 0.00876 -0.00802 AFIX 137 H00P 2 0.289991 0.221213 0.091423 11.00000 -1.50000 H00Q 2 0.288233 0.200791 -0.051241 11.00000 -1.50000 H00R 2 0.213733 0.311915 -0.022446 11.00000 -1.50000 AFIX 0 C00Q 1 0.237604 0.645526 0.535948 11.00000 0.02542 0.02876 = 0.03275 -0.01329 0.01749 -0.00819 AFIX 93 H00S 2 0.261946 0.581417 0.594937 11.00000 -1.20000 H00T 2 0.214373 0.718897 0.561993 11.00000 -1.20000 AFIX 0 C00R 1 0.874434 0.605056 0.341270 11.00000 0.01429 0.04233 = 0.02204 -0.00496 0.00847 -0.00068 AFIX 43 H00U 2 0.948245 0.615264 0.317056 11.00000 -1.20000 AFIX 0 C00S 1 0.075342 0.525230 0.139368 11.00000 0.01768 0.02745 = 0.02056 0.00198 0.00606 -0.00344 AFIX 43 H00V 2 0.102341 0.601902 0.126312 11.00000 -1.20000 AFIX 0 C00T 1 -0.039576 0.473440 0.043377 11.00000 0.01825 0.04092 = 0.02082 0.00369 0.00220 -0.00215 AFIX 43 H00W 2 -0.088057 0.515966 -0.033460 11.00000 -1.20000 AFIX 0 C00U 1 0.823245 0.492222 0.344689 11.00000 0.01600 0.03435 = 0.03192 -0.00940 0.01057 0.00455 AFIX 43 H00X 2 0.862507 0.425600 0.322357 11.00000 -1.20000 AFIX 0 HKLF 4 REM 20201124_sc-13-56a_a.res in P2(1) REM wR2 = 0.0498, GooF = S = 1.067, Restrained GooF = 1.067 for all data REM R1 = 0.0192 for 4759 Fo > 4sig(Fo) and 0.0193 for all 4773 data REM 274 parameters refined using 1 restraints END WGHT 0.0280 0.5140 REM Highest difference peak 0.224, deepest hole -0.497, 1-sigma level 0.056 Q1 1 0.6725 0.8650 0.3770 11.00000 0.05 0.22 Q2 1 0.3228 0.5733 0.6320 11.00000 0.05 0.20 Q3 1 0.0996 0.6266 0.2941 11.00000 0.05 0.18 Q4 1 0.1028 0.5061 0.2117 11.00000 0.05 0.18 Q5 1 1.0795 0.9770 0.4055 11.00000 0.05 0.17 Q6 1 0.1965 0.7139 0.6047 11.00000 0.05 0.17 ; _shelx_res_checksum 89849 _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 1.714 _oxdiff_exptl_absorpt_empirical_full_min 0.700 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, 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 0.89260(3) 0.85670(3) 0.37961(3) 0.02832(8) Uani 1 1 d . . . . . Br02 Br -0.06464(3) 0.14327(3) 0.20618(3) 0.03181(9) Uani 1 1 d . . . . . O003 O 0.41482(18) 0.43357(16) 0.13953(17) 0.0162(4) Uani 1 1 d . . . . . O004 O 0.42139(19) 0.31684(16) 0.31250(18) 0.0178(4) Uani 1 1 d . . . . . N005 N 0.3594(2) 0.7176(2) 0.1694(2) 0.0204(5) Uani 1 1 d . . . . . C006 C 0.5783(3) 0.4998(3) 0.6836(3) 0.0257(6) Uani 1 1 d . . . . . H00A H 0.573218 0.580056 0.704695 0.031 Uiso 1 1 calc R U . . . H00B H 0.596501 0.441258 0.748876 0.031 Uiso 1 1 calc R U . . . C007 C 0.1081(2) 0.3472(3) 0.2715(2) 0.0174(5) Uani 1 1 d . . . . . H007 H 0.157506 0.303349 0.346945 0.021 Uiso 1 1 calc R U . . . C008 C 0.3761(2) 0.6325(2) 0.2339(2) 0.0140(5) Uani 1 1 d . . . . . C009 C -0.0072(3) 0.2984(3) 0.1753(3) 0.0211(5) Uani 1 1 d . . . . . C00A C 0.6510(2) 0.5760(2) 0.4118(2) 0.0151(5) Uani 1 1 d . . . . . C00B C 0.1492(2) 0.4623(2) 0.2542(2) 0.0166(5) Uani 1 1 d . . . . . C00C C 0.5596(3) 0.4690(2) 0.5614(3) 0.0176(5) Uani 1 1 d . . . . . H00C H 0.565031 0.388337 0.542253 0.021 Uiso 1 1 calc R U . . . C00D C 0.2360(2) 0.6324(3) 0.4152(3) 0.0195(5) Uani 1 1 d . . . . . H00D H 0.211349 0.697751 0.357969 0.023 Uiso 1 1 calc R U . . . C00E C 0.4195(3) 0.3339(2) 0.0491(2) 0.0202(5) Uani 1 1 d . . . . . C00F C 0.4135(2) 0.4123(2) 0.2588(2) 0.0137(5) Uani 1 1 d . . . . . C00G C 0.2724(2) 0.5161(2) 0.3656(2) 0.0150(5) Uani 1 1 d . . . . . H00G H 0.298656 0.459227 0.439659 0.018 Uiso 1 1 calc R U . . . C00H C 0.5295(2) 0.5603(2) 0.4507(2) 0.0136(5) Uani 1 1 d . . . . . H00H H 0.514000 0.637513 0.485462 0.016 Uiso 1 1 calc R U . . . C00I C 0.7013(2) 0.6906(2) 0.4075(2) 0.0160(5) Uani 1 1 d . . . . . H00I H 0.660280 0.757863 0.426378 0.019 Uiso 1 1 calc R U . . . C00J C 0.7134(3) 0.4775(3) 0.3813(3) 0.0213(5) Uani 1 1 d . . . . . H00J H 0.681065 0.400725 0.385481 0.026 Uiso 1 1 calc R U . . . C00K C 0.8145(3) 0.7025(3) 0.3743(3) 0.0197(5) Uani 1 1 d . . . . . C00L C 0.3981(2) 0.5303(2) 0.3252(2) 0.0133(5) Uani 1 1 d . . . . . C00M C -0.0821(3) 0.3600(3) 0.0611(3) 0.0262(6) Uani 1 1 d . . . . . H00M H -0.159098 0.326062 -0.002280 0.031 Uiso 1 1 calc R U . . . C00N C 0.4219(3) 0.4046(3) -0.0692(3) 0.0276(6) Uani 1 1 d . . . . . H00E H 0.342848 0.454471 -0.103506 0.041 Uiso 1 1 calc R U . . . H00F H 0.422787 0.349890 -0.136791 0.041 Uiso 1 1 calc R U . . . H00K H 0.501532 0.453863 -0.041919 0.041 Uiso 1 1 calc R U . . . C00O C 0.5482(3) 0.2614(3) 0.1120(3) 0.0246(6) Uani 1 1 d . . . . . H00L H 0.624821 0.314421 0.140143 0.037 Uiso 1 1 calc R U . . . H00N H 0.555894 0.205378 0.048472 0.037 Uiso 1 1 calc R U . . . H00O H 0.545439 0.218557 0.187152 0.037 Uiso 1 1 calc R U . . . C00P C 0.2911(3) 0.2602(3) 0.0134(3) 0.0288(6) Uani 1 1 d . . . . . H00P H 0.289991 0.221213 0.091423 0.043 Uiso 1 1 calc R U . . . H00Q H 0.288233 0.200791 -0.051241 0.043 Uiso 1 1 calc R U . . . H00R H 0.213733 0.311915 -0.022446 0.043 Uiso 1 1 calc R U . . . C00Q C 0.2376(3) 0.6455(3) 0.5359(3) 0.0271(6) Uani 1 1 d . . . . . H00S H 0.261946 0.581417 0.594937 0.032 Uiso 1 1 calc R U . . . H00T H 0.214373 0.718897 0.561993 0.032 Uiso 1 1 calc R U . . . C00R C 0.8744(3) 0.6051(3) 0.3413(3) 0.0258(6) Uani 1 1 d . . . . . H00U H 0.948245 0.615264 0.317056 0.031 Uiso 1 1 calc R U . . . C00S C 0.0753(3) 0.5252(3) 0.1394(3) 0.0223(6) Uani 1 1 d . . . . . H00V H 0.102341 0.601902 0.126312 0.027 Uiso 1 1 calc R U . . . C00T C -0.0396(3) 0.4734(3) 0.0434(3) 0.0282(6) Uani 1 1 d . . . . . H00W H -0.088057 0.515966 -0.033460 0.034 Uiso 1 1 calc R U . . . C00U C 0.8232(3) 0.4922(3) 0.3447(3) 0.0270(6) Uani 1 1 d . . . . . H00X H 0.862507 0.425600 0.322357 0.032 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 0.02359(14) 0.03297(17) 0.02963(14) 0.00191(13) 0.01153(11) -0.01077(12) Br02 0.03448(16) 0.02789(16) 0.03671(16) -0.01058(13) 0.01769(13) -0.01606(13) O003 0.0204(9) 0.0165(9) 0.0134(8) -0.0001(7) 0.0082(7) 0.0020(7) O004 0.0220(9) 0.0151(9) 0.0174(8) -0.0006(7) 0.0087(7) 0.0002(7) N005 0.0174(10) 0.0224(12) 0.0214(11) 0.0030(9) 0.0073(9) 0.0019(9) C006 0.0367(16) 0.0221(14) 0.0184(14) 0.0038(11) 0.0107(12) 0.0015(11) C007 0.0161(11) 0.0209(13) 0.0176(10) -0.0031(11) 0.0090(9) -0.0038(10) C008 0.0105(10) 0.0151(12) 0.0158(10) -0.0014(10) 0.0043(8) 0.0004(10) C009 0.0213(13) 0.0233(14) 0.0242(13) -0.0077(11) 0.0149(11) -0.0068(10) C00A 0.0115(11) 0.0199(12) 0.0123(10) 0.0002(9) 0.0026(9) 0.0011(10) C00B 0.0127(11) 0.0209(13) 0.0174(12) -0.0020(10) 0.0071(9) -0.0011(10) C00C 0.0173(12) 0.0156(12) 0.0183(12) 0.0001(10) 0.0050(10) -0.0011(10) C00D 0.0134(11) 0.0199(13) 0.0267(12) -0.0042(11) 0.0093(9) -0.0026(10) C00E 0.0271(13) 0.0192(14) 0.0156(11) -0.0035(10) 0.0098(10) 0.0019(11) C00F 0.0098(10) 0.0174(12) 0.0142(11) -0.0012(9) 0.0049(9) -0.0001(9) C00G 0.0131(11) 0.0176(12) 0.0152(11) -0.0007(9) 0.0066(9) -0.0011(9) C00H 0.0121(11) 0.0135(11) 0.0139(11) -0.0006(9) 0.0037(9) 0.0002(9) C00I 0.0141(11) 0.0202(12) 0.0128(11) -0.0011(9) 0.0042(9) 0.0010(9) C00J 0.0159(12) 0.0211(13) 0.0264(13) -0.0039(11) 0.0075(11) 0.0008(10) C00K 0.0151(12) 0.0281(15) 0.0154(12) 0.0007(11) 0.0054(10) -0.0043(11) C00L 0.0117(10) 0.0140(12) 0.0142(11) 0.0012(9) 0.0050(9) 0.0000(9) C00M 0.0166(11) 0.0391(16) 0.0208(12) -0.0084(13) 0.0049(9) -0.0082(13) C00N 0.0370(16) 0.0311(16) 0.0180(13) -0.0001(11) 0.0141(12) 0.0045(12) C00O 0.0312(15) 0.0241(14) 0.0219(13) -0.0021(11) 0.0139(11) 0.0076(12) C00P 0.0331(15) 0.0303(16) 0.0214(13) -0.0111(12) 0.0088(12) -0.0080(13) C00Q 0.0254(13) 0.0288(14) 0.0327(14) -0.0133(14) 0.0175(11) -0.0082(13) C00R 0.0143(11) 0.0423(18) 0.0220(13) -0.0050(12) 0.0085(10) -0.0007(11) C00S 0.0177(12) 0.0274(15) 0.0206(13) 0.0020(11) 0.0061(10) -0.0034(11) C00T 0.0183(13) 0.0409(17) 0.0208(13) 0.0037(12) 0.0022(11) -0.0021(12) C00U 0.0160(13) 0.0344(17) 0.0319(15) -0.0094(13) 0.0106(12) 0.0045(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 C00F O003 C00E 121.9(2) . . ? H00A C006 H00B 120.0 . . ? C00C C006 H00A 120.0 . . ? C00C C006 H00B 120.0 . . ? C009 C007 H007 120.2 . . ? C009 C007 C00B 119.6(2) . . ? C00B C007 H007 120.2 . . ? N005 C008 C00L 175.3(3) . . ? C007 C009 Br02 118.3(2) . . ? C00M C009 Br02 119.8(2) . . ? C00M C009 C007 121.9(3) . . ? C00I C00A C00H 119.8(2) . . ? C00J C00A C00H 120.9(2) . . ? C00J C00A C00I 119.3(2) . . ? C007 C00B C00G 118.2(2) . . ? C00S C00B C007 119.2(2) . . ? C00S C00B C00G 122.6(2) . . ? C006 C00C H00C 118.8 . . ? C006 C00C C00H 122.5(3) . . ? C00H C00C H00C 118.8 . . ? C00G C00D H00D 118.5 . . ? C00Q C00D H00D 118.5 . . ? C00Q C00D C00G 123.1(3) . . ? O003 C00E C00N 101.0(2) . . ? O003 C00E C00O 110.5(2) . . ? O003 C00E C00P 108.4(2) . . ? C00O C00E C00N 110.7(2) . . ? C00O C00E C00P 113.8(2) . . ? C00P C00E C00N 111.7(2) . . ? O003 C00F C00L 110.7(2) . . ? O004 C00F O003 127.7(2) . . ? O004 C00F C00L 121.7(2) . . ? C00B C00G H00G 106.9 . . ? C00B C00G C00L 112.50(19) . . ? C00D C00G C00B 111.0(2) . . ? C00D C00G H00G 106.9 . . ? C00D C00G C00L 112.2(2) . . ? C00L C00G H00G 106.9 . . ? C00A C00H H00H 107.2 . . ? C00A C00H C00L 110.67(19) . . ? C00C C00H C00A 110.9(2) . . ? C00C C00H H00H 107.2 . . ? C00C C00H C00L 113.4(2) . . ? C00L C00H H00H 107.2 . . ? C00A C00I H00I 120.7 . . ? C00A C00I C00K 118.7(2) . . ? C00K C00I H00I 120.7 . . ? C00A C00J H00J 119.6 . . ? C00U C00J C00A 120.8(3) . . ? C00U C00J H00J 119.6 . . ? C00I C00K Br01 119.5(2) . . ? C00R C00K Br01 118.5(2) . . ? C00R C00K C00I 122.0(3) . . ? C008 C00L C00F 111.0(2) . . ? C008 C00L C00G 109.6(2) . . ? C008 C00L C00H 106.44(19) . . ? C00F C00L C00G 107.6(2) . . ? C00F C00L C00H 111.69(19) . . ? C00G C00L C00H 110.47(19) . . ? C009 C00M H00M 120.9 . . ? C009 C00M C00T 118.3(3) . . ? C00T C00M H00M 120.9 . . ? C00E C00N H00E 109.5 . . ? C00E C00N H00F 109.5 . . ? C00E C00N H00K 109.5 . . ? H00E C00N H00F 109.5 . . ? H00E C00N H00K 109.5 . . ? H00F C00N H00K 109.5 . . ? C00E C00O H00L 109.5 . . ? C00E C00O H00N 109.5 . . ? C00E C00O H00O 109.5 . . ? H00L C00O H00N 109.5 . . ? H00L C00O H00O 109.5 . . ? H00N C00O H00O 109.5 . . ? C00E C00P H00P 109.5 . . ? C00E C00P H00Q 109.5 . . ? C00E C00P H00R 109.5 . . ? H00P C00P H00Q 109.5 . . ? H00P C00P H00R 109.5 . . ? H00Q C00P H00R 109.5 . . ? C00D C00Q H00S 120.0 . . ? C00D C00Q H00T 120.0 . . ? H00S C00Q H00T 120.0 . . ? C00K C00R H00U 120.6 . . ? C00U C00R C00K 118.9(2) . . ? C00U C00R H00U 120.6 . . ? C00B C00S H00V 119.9 . . ? C00B C00S C00T 120.1(3) . . ? C00T C00S H00V 119.9 . . ? C00M C00T C00S 120.9(3) . . ? C00M C00T H00W 119.5 . . ? C00S C00T H00W 119.5 . . ? C00J C00U H00X 119.8 . . ? C00R C00U C00J 120.3(3) . . ? C00R C00U H00X 119.8 . . ? 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 C00K 1.901(3) . ? Br02 C009 1.906(3) . ? O003 C00E 1.499(3) . ? O003 C00F 1.329(3) . ? O004 C00F 1.202(3) . ? N005 C008 1.154(4) . ? C006 H00A 0.9300 . ? C006 H00B 0.9300 . ? C006 C00C 1.318(4) . ? C007 H007 0.9300 . ? C007 C009 1.389(4) . ? C007 C00B 1.392(4) . ? C008 C00L 1.473(3) . ? C009 C00M 1.380(4) . ? C00A C00H 1.523(3) . ? C00A C00I 1.393(4) . ? C00A C00J 1.390(4) . ? C00B C00G 1.533(3) . ? C00B C00S 1.389(4) . ? C00C H00C 0.9300 . ? C00C C00H 1.517(3) . ? C00D H00D 0.9300 . ? C00D C00G 1.511(4) . ? C00D C00Q 1.321(4) . ? C00E C00N 1.522(4) . ? C00E C00O 1.515(4) . ? C00E C00P 1.517(4) . ? C00F C00L 1.541(3) . ? C00G H00G 0.9800 . ? C00G C00L 1.574(3) . ? C00H H00H 0.9800 . ? C00H C00L 1.579(3) . ? C00I H00I 0.9300 . ? C00I C00K 1.395(4) . ? C00J H00J 0.9300 . ? C00J C00U 1.388(4) . ? C00K C00R 1.378(4) . ? C00M H00M 0.9300 . ? C00M C00T 1.381(5) . ? C00N H00E 0.9600 . ? C00N H00F 0.9600 . ? C00N H00K 0.9600 . ? C00O H00L 0.9600 . ? C00O H00N 0.9600 . ? C00O H00O 0.9600 . ? C00P H00P 0.9600 . ? C00P H00Q 0.9600 . ? C00P H00R 0.9600 . ? C00Q H00S 0.9300 . ? C00Q H00T 0.9300 . ? C00R H00U 0.9300 . ? C00R C00U 1.377(5) . ? C00S H00V 0.9300 . ? C00S C00T 1.399(4) . ? C00T H00W 0.9300 . ? C00U 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 C00K C00R C00U 176.3(2) . . . . ? Br02 C009 C00M C00T 178.4(2) . . . . ? O003 C00F C00L C008 5.4(3) . . . . ? O003 C00F C00L C00G 125.3(2) . . . . ? O003 C00F C00L C00H -113.2(2) . . . . ? O004 C00F C00L C008 -173.9(2) . . . . ? O004 C00F C00L C00G -54.0(3) . . . . ? O004 C00F C00L C00H 67.4(3) . . . . ? C006 C00C C00H C00A 108.2(3) . . . . ? C006 C00C C00H C00L -126.6(3) . . . . ? C007 C009 C00M C00T 0.1(4) . . . . ? C007 C00B C00G C00D -121.8(2) . . . . ? C007 C00B C00G C00L 111.4(2) . . . . ? C007 C00B C00S C00T 0.6(4) . . . . ? C009 C007 C00B C00G 176.7(2) . . . . ? C009 C007 C00B C00S -1.3(4) . . . . ? C009 C00M C00T C00S -0.8(4) . . . . ? C00A C00H C00L C008 -60.2(3) . . . . ? C00A C00H C00L C00F 61.1(3) . . . . ? C00A C00H C00L C00G -179.1(2) . . . . ? C00A C00I C00K Br01 -175.70(18) . . . . ? C00A C00I C00K C00R 2.4(4) . . . . ? C00A C00J C00U C00R 1.6(4) . . . . ? C00B C007 C009 Br02 -177.35(18) . . . . ? C00B C007 C009 C00M 1.0(4) . . . . ? C00B C00G C00L C008 74.6(3) . . . . ? C00B C00G C00L C00F -46.2(3) . . . . ? C00B C00G C00L C00H -168.4(2) . . . . ? C00B C00S C00T C00M 0.5(5) . . . . ? C00C C00H C00L C008 174.5(2) . . . . ? C00C C00H C00L C00F -64.2(3) . . . . ? C00C C00H C00L C00G 55.6(3) . . . . ? C00D C00G C00L C008 -51.4(3) . . . . ? C00D C00G C00L C00F -172.3(2) . . . . ? C00D C00G C00L C00H 65.5(3) . . . . ? C00E O003 C00F O004 3.4(4) . . . . ? C00E O003 C00F C00L -175.9(2) . . . . ? C00F O003 C00E C00N -179.0(2) . . . . ? C00F O003 C00E C00O -61.8(3) . . . . ? C00F O003 C00E C00P 63.5(3) . . . . ? C00G C00B C00S C00T -177.3(2) . . . . ? C00H C00A C00I C00K 178.6(2) . . . . ? C00H C00A C00J C00U 179.4(2) . . . . ? C00I C00A C00H C00C -127.8(2) . . . . ? C00I C00A C00H C00L 105.5(3) . . . . ? C00I C00A C00J C00U -1.1(4) . . . . ? C00I C00K C00R C00U -1.8(4) . . . . ? C00J C00A C00H C00C 51.7(3) . . . . ? C00J C00A C00H C00L -75.0(3) . . . . ? C00J C00A C00I C00K -0.9(4) . . . . ? C00K C00R C00U C00J -0.2(4) . . . . ? C00Q C00D C00G C00B 114.1(3) . . . . ? C00Q C00D C00G C00L -119.0(3) . . . . ? C00S C00B C00G C00D 56.1(3) . . . . ? C00S C00B C00G C00L -70.6(3) . . . . ?