#------------------------------------------------------------------------------ #$Date: 2024-12-06 18:25:34 +0200 (Fri, 06 Dec 2024) $ #$Revision: 296365 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/27/1572702.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_1572702 loop_ _publ_author_name 'Jin, Ke' 'Xiao, Zuo' 'Xie, Huidong' 'Shen, Xingxing' 'Wang, Jizheng' 'Chen, Xiangyu' 'Wang, Zhijie' 'Zhao, Zujin' 'Yan, Keyou' 'Ding, Yong' 'Ding, Liming' _publ_section_title ; Tether-entangled conjugated helices. ; _journal_issue 41 _journal_name_full 'Chemical science' _journal_page_first 17128 _journal_page_last 17149 _journal_paper_doi 10.1039/d4sc04796f _journal_volume 15 _journal_year 2024 _chemical_absolute_configuration ab _chemical_formula_moiety 'C32 H36 Br2 N2 O4' _chemical_formula_sum 'C32 H36 Br2 N2 O4' _chemical_formula_weight 672.45 _chemical_name_systematic 1 _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 2022-10-08 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2024-05-11 deposited with the CCDC. 2024-09-27 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 94.228(2) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 9.0653(2) _cell_length_b 8.3658(2) _cell_length_c 20.4585(5) _cell_measurement_reflns_used 11090 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 68.1390 _cell_measurement_theta_min 2.2050 _cell_volume 1547.32(6) _computing_cell_refinement 'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)' _computing_data_collection 'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)' _computing_data_reduction 'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)' _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 293 _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 10.0000 _diffrn_measured_fraction_theta_full 0.985 _diffrn_measured_fraction_theta_max 0.981 _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 -28.00 3.00 0.50 0.50 -- 42.20 -82.00 -30.00 62 2 \w 14.00 91.00 0.50 0.50 -- 42.20 54.00 30.00 154 3 \w 1.00 35.00 0.50 0.50 -- 42.20 -82.00 120.00 68 4 \w 29.00 69.00 0.50 0.50 -- 42.20 -82.00 -30.00 80 5 \w 90.00 130.00 0.50 0.50 -- 42.20 77.00 -90.00 80 6 \w 107.00 132.00 0.50 0.50 -- 42.20 54.00 30.00 50 7 \w -3.00 22.00 0.50 0.50 -- 42.20 -82.00 150.00 50 8 \w 41.00 66.00 0.50 0.50 -- 42.20 -82.00 120.00 50 9 \w -1.00 54.00 0.50 0.50 -- 42.20 -65.00 -90.00 110 10 \w -33.00 1.00 0.50 0.50 -- 42.20 -77.00-120.00 68 11 \w 26.00 68.00 0.50 0.50 -- 42.20 -82.00-180.00 84 12 \w -45.00 15.00 0.50 0.50 -- 42.20 -82.00-180.00 120 13 \w 29.00 67.00 0.50 0.50 -- 42.20 -65.00 0.00 76 14 \w 67.00 110.00 0.50 0.50 -- 42.20 82.00 30.00 86 15 \w 9.00 65.00 0.50 0.50 -- 42.20 -77.00-120.00 112 16 \w 27.00 53.00 0.50 0.50 -- 42.20 77.00 -90.00 52 17 \w 30.00 64.00 0.50 0.50 -- 42.20 -77.00 120.00 68 18 \w -43.00 -1.00 0.50 0.50 -- 42.20 -77.00 120.00 84 19 \w 59.00 84.00 0.50 0.50 -- 42.20 77.00 -90.00 50 20 \w 38.00 78.00 0.50 0.50 -- 93.70 -82.00 -30.00 80 21 \w 66.00 121.00 0.50 0.50 -- 93.70 -59.00 90.00 110 22 \w 9.00 107.00 0.50 0.50 -- 93.70 -82.00 90.00 196 23 \w 6.00 62.00 0.50 0.50 -- 93.70 -59.00 90.00 112 24 \w 15.00 128.00 0.50 0.50 -- 93.70 -33.00 -90.00 226 25 \w 64.00 107.00 0.50 0.50 -- 93.70 -82.00 150.00 86 26 \w 54.00 102.00 0.50 0.50 -- 93.70 -33.00 90.00 96 27 \w 4.00 48.00 0.50 0.50 -- 93.70 -82.00 150.00 88 28 \w 10.00 117.00 0.50 0.50 -- 93.70 -82.00 -60.00 214 29 \w 60.00 122.00 0.50 0.50 -- 93.70 -42.00 150.00 124 30 \w 4.00 134.00 0.50 0.50 -- 93.70 17.00 -90.00 260 31 \w 52.00 103.00 0.50 0.50 -- 93.70 -82.00-150.00 102 32 \w 4.00 37.00 0.50 0.50 -- 93.70 -33.00 90.00 66 33 \w 68.00 93.00 0.50 0.50 -- 93.70 -82.00 120.00 50 34 \w 51.00 85.00 0.50 0.50 -- 93.70 -82.00-120.00 68 35 \w 4.00 183.00 0.50 0.50 -- 93.70 8.00 90.00 358 36 \w 28.00 55.00 0.50 0.50 -- 93.70 -77.00 60.00 54 37 \w 54.00 102.00 0.50 0.50 -- 93.70 -82.00 30.00 96 38 \w 46.00 93.00 0.50 0.50 -- 93.70 -82.00 -90.00 94 39 \w 74.00 100.00 0.50 0.50 -- 93.70 -82.00 0.00 52 40 \w 61.00 86.00 0.50 0.50 -- 93.70 -82.00 60.00 50 41 \w 32.00 118.00 0.50 0.50 -- 93.70 -50.00 -60.00 172 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Pro II 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 0.0598101000 _diffrn_orient_matrix_UB_12 -0.0882058000 _diffrn_orient_matrix_UB_13 -0.0586081000 _diffrn_orient_matrix_UB_21 -0.0597629000 _diffrn_orient_matrix_UB_22 -0.1590873000 _diffrn_orient_matrix_UB_23 0.0252742000 _diffrn_orient_matrix_UB_31 -0.1479384000 _diffrn_orient_matrix_UB_32 0.0285607000 _diffrn_orient_matrix_UB_33 -0.0403714000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0540 _diffrn_reflns_av_unetI/netI 0.0511 _diffrn_reflns_Laue_measured_fraction_full 0.985 _diffrn_reflns_Laue_measured_fraction_max 0.981 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_number 13231 _diffrn_reflns_point_group_measured_fraction_full 0.950 _diffrn_reflns_point_group_measured_fraction_max 0.943 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 68.379 _diffrn_reflns_theta_min 2.165 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'Rigaku (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 3.627 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.11001 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.41.89a (Rigaku Oxford Diffraction, 2020) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.443 _exptl_crystal_description block _exptl_crystal_F_000 688 _exptl_crystal_size_max 0.06 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.04 _refine_diff_density_max 1.580 _refine_diff_density_min -0.951 _refine_diff_density_rms 0.139 _refine_ls_abs_structure_details ; Flack x determined using 2010 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.04(2) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 363 _refine_ls_number_reflns 5342 _refine_ls_number_restraints 202 _refine_ls_restrained_S_all 1.099 _refine_ls_R_factor_all 0.0765 _refine_ls_R_factor_gt 0.0753 _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^)+(0.1544P)^2^+1.1578P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2080 _refine_ls_wR_factor_ref 0.2102 _reflns_Friedel_coverage 0.790 _reflns_Friedel_fraction_full 0.910 _reflns_Friedel_fraction_max 0.899 _reflns_number_gt 5101 _reflns_number_total 5342 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4sc04796f2.cif _cod_data_source_block kyg_auto _cod_depositor_comments 'Adding full bibliography for 1572702--1572708.cif.' _cod_database_code 1572702 _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 0.868 _shelx_estimated_absorpt_t_min 0.812 _diffrn_oxdiff_digest_frames ; 01cb684a0709e5665410b2b42591f0d96e042589135 ; _diffrn_oxdiff_digest_hkl ; 01adcb971cbac685d099a9162a908d3c4a890e ; _reflns_odcompleteness_completeness 98.58 _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. Restrained distances C18-C17 = C23-C22 1.45 with sigma of 0.002 C22-C21 1.45 with sigma of 0.002 C21-C20 1.45 with sigma of 0.002 C20-C19 1.45 with sigma of 0.002 C19-C18 1.45 with sigma of 0.002 C18-C17 1.45 with sigma of 0.002 C8-C7 1.45 with sigma of 0.002 C26-C25 1.45 with sigma of 0.002 C7-C6 1.45 with sigma of 0.002 C28-C26 1.45 with sigma of 0.002 C29-C28 1.4 with sigma of 0.002 C28-C27 1.4 with sigma of 0.002 C32-C27 1.4 with sigma of 0.002 C32-C31 1.4 with sigma of 0.002 C31-C30 1.4 with sigma of 0.002 C3-C4 1.4 with sigma of 0.002 C4-C5 1.4 with sigma of 0.002 C5-C6 1.4 with sigma of 0.002 C6-C1 1.4 with sigma of 0.002 C1-C2 1.4 with sigma of 0.002 C2-C3 1.4 with sigma of 0.002 C15-C10 1.4 with sigma of 0.002 C10-C11 1.4 with sigma of 0.002 C11-C12 1.4 with sigma of 0.002 C13-C12 1.4 with sigma of 0.002 C14-C13 1.4 with sigma of 0.002 3. Uiso/Uaniso restraints and constraints C24 \\sim C28 \\sim C13 \\sim C10 \\sim C12 \\sim C11 \\sim C27 \\sim C15 \\sim C14 \\sim C32 \\sim C6 \\sim C9 \\sim C7 \\sim C26 \\sim C23 \\sim C1 \\sim C29 \\sim C5 \\sim C2 \\sim C31 \\sim C30 \\sim C3 \\sim C25 \\sim C8 \\sim C16 \\sim C4 \\sim C22 \\sim C19 \\sim C18 \\sim C21 \\sim C20 \\sim C17: within 2A with sigma of 0.004 and sigma for terminal atoms of 0.008 4.a Ternary CH refined with riding coordinates: C7(H7), C26(H26) 4.b Secondary CH2 refined with riding coordinates: C23(H23A,H23B), C16(H16A,H16B), C22(H22A,H22B), C19(H19A,H19B), C18(H18A, H18B), C21(H21A,H21B), C20(H20A,H20B), C17(H17A,H17B) 4.c Aromatic/amide H refined with riding coordinates: C11(H11), C27(H27), C14(H14), C32(H32), C1(H1), C29(H29), C5(H5), C2(H2), C31(H31), C30(H30), C3(H3), C4(H4) 4.d Idealised Me refined as rotating group: C25(H25A,H25B,H25C), C8(H8A,H8B,H8C) ; _shelx_res_file ; TITL kyg_auto_a.res in P2(1) kyg_auto.res created by SHELXL-2018/3 at 13:41:05 on 08-Oct-2022 REM Old TITL kyg_auto_a.res in P2(1) REM SHELXT solution in P2(1): R1 0.159, Rweak 0.043, Alpha 0.005 REM 2.596 for 5 systematic absences, Orientation as input REM Flack x = 0.037 ( 0.018 ) from 2120 Parsons' quotients REM Formula found by SHELXT: C31 Br2 N3 O4 CELL 1.54184 9.0653 8.3658 20.4585 90 94.228 90 ZERR 2 0.0002 0.0002 0.0005 0 0.002 0 LATT -1 SYMM -X,0.5+Y,-Z SFAC C H Br N O UNIT 64 72 4 4 8 DFIX 1.45 0.002 C18 C17 C23 C22 DFIX 1.45 0.002 C22 C21 DFIX 1.45 0.002 C21 C20 DFIX 1.45 0.002 C20 C19 DFIX 1.45 0.002 C19 C18 DFIX 1.45 0.002 C18 C17 DFIX 1.45 0.002 C8 C7 DFIX 1.45 0.002 C26 C25 DFIX 1.45 0.002 C7 C6 DFIX 1.45 0.002 C28 C26 DFIX 1.4 0.002 C29 C28 DFIX 1.4 0.002 C28 C27 DFIX 1.4 0.002 C32 C27 DFIX 1.4 0.002 C32 C31 DFIX 1.4 0.002 C31 C30 DFIX 1.4 0.002 C3 C4 DFIX 1.4 0.002 C4 C5 DFIX 1.4 0.002 C5 C6 DFIX 1.4 0.002 C6 C1 DFIX 1.4 0.002 C1 C2 DFIX 1.4 0.002 C2 C3 DFIX 1.4 0.002 C15 C10 DFIX 1.4 0.002 C10 C11 DFIX 1.4 0.002 C11 C12 DFIX 1.4 0.002 C13 C12 DFIX 1.4 0.002 C14 C13 SIMU 0.004 0.008 2 $C L.S. 40 PLAN 14 SIZE 0.04 0.05 0.06 TEMP 19.85 list 4 fmap 2 acta REM REM REM WGHT 0.154400 1.157800 FVAR 0.63771 BR2 3 0.973063 0.703681 0.238682 11.00000 0.02681 0.05694 = 0.05812 -0.01688 -0.01095 0.00391 BR1 3 0.293865 0.518569 0.144750 11.00000 0.02925 0.09560 = 0.06275 -0.01503 0.00171 -0.01844 O2 5 0.886575 0.306860 0.209365 11.00000 0.04709 0.03996 = 0.03483 0.00857 0.00891 0.01455 O1 5 1.030751 0.268353 0.125340 11.00000 0.03971 0.05229 = 0.04955 -0.00783 0.01373 0.01103 O3 5 0.430049 0.693863 0.328169 11.00000 0.05100 0.04455 = 0.02925 -0.00092 0.00346 0.00564 O4 5 0.265754 0.896758 0.312963 11.00000 0.04755 0.06201 = 0.05089 0.00398 0.01480 0.02168 N1 4 0.861205 0.471747 0.125018 11.00000 0.03973 0.03848 = 0.02736 0.00246 0.00527 0.00253 N2 4 0.402727 0.813401 0.230251 11.00000 0.02995 0.04748 = 0.03460 0.00223 -0.00094 0.01295 C24 1 0.936607 0.340775 0.151307 11.00000 0.02740 0.03094 = 0.03436 -0.00670 0.00508 -0.00161 C28 1 0.858353 0.130590 0.295857 11.00000 0.04436 0.02940 = 0.04110 -0.00314 0.00201 0.00094 C13 1 0.777248 0.656817 0.208038 11.00000 0.02391 0.03213 = 0.02645 -0.00281 -0.00496 -0.00024 C10 1 0.486236 0.586224 0.167479 11.00000 0.02523 0.04090 = 0.02810 0.00100 0.00085 -0.00663 C12 1 0.749705 0.541921 0.159010 11.00000 0.03125 0.02993 = 0.02536 0.00123 -0.00083 0.00272 C11 1 0.602085 0.503746 0.141030 11.00000 0.03279 0.03551 = 0.02860 0.00059 0.00018 -0.00104 AFIX 43 H11 2 0.580586 0.422113 0.110970 11.00000 -1.20000 AFIX 0 C27 1 0.709340 0.176006 0.293005 11.00000 0.04662 0.03546 = 0.04974 0.00189 0.00538 -0.00136 AFIX 43 H27 2 0.674303 0.245699 0.260008 11.00000 -1.20000 AFIX 0 C15 1 0.519457 0.711481 0.211394 11.00000 0.03010 0.03861 = 0.02778 0.00244 -0.00090 0.00367 C14 1 0.660581 0.741938 0.232580 11.00000 0.02993 0.03623 = 0.02937 -0.00474 -0.00483 0.00528 AFIX 43 H14 2 0.680916 0.820762 0.264013 11.00000 -1.20000 AFIX 0 C32 1 0.610728 0.121314 0.337537 11.00000 0.05580 0.04407 = 0.05485 0.00043 0.01003 -0.00551 AFIX 43 H32 2 0.512798 0.155348 0.334387 11.00000 -1.20000 AFIX 0 C6 1 0.540452 0.628239 0.430232 11.00000 0.06430 0.05136 = 0.03311 -0.00122 -0.00218 -0.00220 C9 1 0.358243 0.810142 0.292268 11.00000 0.02806 0.03813 = 0.03566 0.00233 0.00220 0.00115 C7 1 0.402959 0.683212 0.396784 11.00000 0.05917 0.04979 = 0.02891 -0.00416 0.00285 -0.00545 AFIX 13 H7 2 0.380153 0.790059 0.412894 11.00000 -1.20000 AFIX 0 C26 1 0.964205 0.187035 0.251105 11.00000 0.04122 0.03083 = 0.04370 -0.00146 0.00187 0.00952 AFIX 13 H26 2 0.992337 0.097560 0.223715 11.00000 -1.20000 AFIX 0 C23 1 0.885666 0.527902 0.058749 11.00000 0.09019 0.07433 = 0.04096 0.02037 0.02011 0.00921 AFIX 23 H23A 2 0.973671 0.475279 0.045114 11.00000 -1.20000 H23B 2 0.803181 0.491404 0.029660 11.00000 -1.20000 AFIX 0 C1 1 0.578557 0.674278 0.495036 11.00000 0.07286 0.06159 = 0.03699 0.00039 -0.00937 -0.00197 AFIX 43 H1 2 0.517143 0.743539 0.516003 11.00000 -1.20000 AFIX 0 C29 1 0.902606 0.021959 0.345615 11.00000 0.05518 0.03710 = 0.04019 0.00028 -0.00146 -0.00119 AFIX 43 H29 2 1.000462 -0.012320 0.348980 11.00000 -1.20000 AFIX 0 C5 1 0.636346 0.521893 0.401878 11.00000 0.07098 0.06478 = 0.04267 -0.00297 -0.00808 0.00669 AFIX 43 H5 2 0.612376 0.487945 0.359124 11.00000 -1.20000 AFIX 0 C2 1 0.707954 0.617342 0.528654 11.00000 0.07963 0.07490 = 0.04489 0.00100 -0.01980 -0.00048 AFIX 43 H2 2 0.729781 0.647648 0.572026 11.00000 -1.20000 AFIX 0 C31 1 0.661584 0.014658 0.386887 11.00000 0.06060 0.04583 = 0.04817 0.00002 0.00858 -0.00982 AFIX 43 H31 2 0.598265 -0.021694 0.417415 11.00000 -1.20000 AFIX 0 C30 1 0.808796 -0.036585 0.389730 11.00000 0.06387 0.04365 = 0.04518 0.00211 0.00297 -0.00425 AFIX 43 H30 2 0.843150 -0.110090 0.421390 11.00000 -1.20000 AFIX 0 C3 1 0.805317 0.515904 0.498598 11.00000 0.08079 0.08134 = 0.05568 0.00229 -0.02172 0.00641 AFIX 43 H3 2 0.893743 0.483696 0.520619 11.00000 -1.20000 AFIX 0 C25 1 1.097322 0.258221 0.282579 11.00000 0.04654 0.05074 = 0.06609 0.00712 -0.00763 0.00082 AFIX 137 H25A 2 1.160244 0.293678 0.249727 11.00000 -1.50000 H25B 2 1.148734 0.180281 0.310143 11.00000 -1.50000 H25C 2 1.070946 0.347739 0.308663 11.00000 -1.50000 AFIX 0 C8 1 0.277635 0.578718 0.404685 11.00000 0.06376 0.08867 = 0.05082 0.01721 -0.00113 -0.01509 AFIX 137 H8A 2 0.194035 0.615276 0.377182 11.00000 -1.50000 H8B 2 0.253727 0.580055 0.449620 11.00000 -1.50000 H8C 2 0.302281 0.471733 0.392475 11.00000 -1.50000 AFIX 0 C16 1 0.333901 0.930113 0.185004 11.00000 0.07498 0.09101 = 0.06550 0.03451 0.01257 0.04012 AFIX 23 H16A 2 0.327828 1.031268 0.207823 11.00000 -1.20000 H16B 2 0.233580 0.895563 0.172612 11.00000 -1.20000 AFIX 0 C4 1 0.766460 0.464069 0.434605 11.00000 0.07823 0.07732 = 0.05546 -0.00094 -0.01364 0.00985 AFIX 43 H4 2 0.826288 0.392191 0.414120 11.00000 -1.20000 AFIX 0 C22 1 0.902741 0.698142 0.048232 11.00000 0.10410 0.08476 = 0.06079 0.02497 0.01912 0.00713 AFIX 23 H22A 2 0.957858 0.714236 0.009890 11.00000 -1.20000 H22B 2 0.960270 0.743378 0.085602 11.00000 -1.20000 AFIX 0 C19 1 0.609962 1.035506 0.052366 11.00000 0.10862 0.10095 = 0.09151 0.02972 0.01772 0.02332 AFIX 23 H19A 2 0.539399 0.985739 0.020709 11.00000 -1.20000 H19B 2 0.622924 1.145828 0.039370 11.00000 -1.20000 AFIX 0 C18 1 0.554215 1.029913 0.117011 11.00000 0.10342 0.09914 = 0.09355 0.03155 0.01447 0.02901 AFIX 23 H18A 2 0.626426 0.973381 0.145740 11.00000 -1.20000 H18B 2 0.550124 1.138793 0.133078 11.00000 -1.20000 AFIX 0 C21 1 0.763196 0.783271 0.039058 11.00000 0.11788 0.09943 = 0.08230 0.02626 0.02101 0.00874 AFIX 23 H21A 2 0.727672 0.768990 -0.006459 11.00000 -1.20000 H21B 2 0.693955 0.728006 0.065099 11.00000 -1.20000 AFIX 0 C20 1 0.750245 0.952150 0.053389 11.00000 0.11892 0.10702 = 0.09294 0.02284 0.02103 0.01729 AFIX 23 H20A 2 0.798738 0.968422 0.096741 11.00000 -1.20000 H20B 2 0.809287 1.008075 0.023002 11.00000 -1.20000 AFIX 0 C17 1 0.411172 0.957196 0.124143 11.00000 0.09333 0.10037 = 0.08613 0.03454 0.01526 0.03659 AFIX 23 H17A 2 0.416829 0.852597 0.104022 11.00000 -1.20000 H17B 2 0.342111 1.018481 0.095646 11.00000 -1.20000 AFIX 0 HKLF 4 REM kyg_auto_a.res in P2(1) REM wR2 = 0.2102, GooF = S = 1.072, Restrained GooF = 1.099 for all data REM R1 = 0.0753 for 5101 Fo > 4sig(Fo) and 0.0765 for all 5342 data REM 363 parameters refined using 202 restraints END WGHT 0.1544 1.1667 REM Highest difference peak 1.580, deepest hole -0.951, 1-sigma level 0.139 Q1 1 0.8808 0.6980 0.2194 11.00000 0.05 1.58 Q2 1 1.0664 0.7020 0.2614 11.00000 0.05 1.37 Q3 1 0.3840 0.5176 0.1689 11.00000 0.05 1.19 Q4 1 0.2020 0.5289 0.1239 11.00000 0.05 1.16 Q5 1 0.8458 0.8380 0.0705 11.00000 0.05 1.08 Q6 1 0.4651 1.0326 0.1539 11.00000 0.05 1.02 Q7 1 0.4854 0.9659 0.0784 11.00000 0.05 0.98 Q8 1 0.6876 0.8580 0.0360 11.00000 0.05 0.84 Q9 1 0.2983 0.6017 0.1210 11.00000 0.05 0.79 Q10 1 0.5715 0.6229 0.4395 11.00000 0.05 0.55 Q11 1 0.1787 0.6994 0.2785 11.00000 0.05 0.52 Q12 1 0.9851 0.6414 0.2061 11.00000 0.05 0.49 Q13 1 1.1354 0.2789 0.1635 11.00000 0.05 0.43 Q14 1 0.7757 0.6931 0.1866 11.00000 0.05 0.42 ; _shelx_res_checksum 44026 _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 2.625 _oxdiff_exptl_absorpt_empirical_full_min 0.291 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 Br2 Br 0.97306(10) 0.7037(3) 0.23868(5) 0.0480(3) Uani 1 1 d . . . . . Br1 Br 0.29387(12) 0.5186(3) 0.14475(6) 0.0626(4) Uani 1 1 d . . . . . O2 O 0.8866(8) 0.3069(8) 0.2094(3) 0.0403(15) Uani 1 1 d . . . . . O1 O 1.0308(8) 0.2684(9) 0.1253(3) 0.0467(16) Uani 1 1 d . . . . . O3 O 0.4300(8) 0.6939(9) 0.3282(3) 0.0416(14) Uani 1 1 d . . . . . O4 O 0.2658(8) 0.8968(10) 0.3130(4) 0.0529(18) Uani 1 1 d . . . . . N1 N 0.8612(9) 0.4717(9) 0.1250(3) 0.0351(16) Uani 1 1 d . . . . . N2 N 0.4027(8) 0.8134(10) 0.2303(4) 0.0375(16) Uani 1 1 d . . . . . C24 C 0.9366(9) 0.3408(10) 0.1513(4) 0.0308(16) Uani 1 1 d . U . . . C28 C 0.8584(7) 0.1306(9) 0.2959(4) 0.0383(14) Uani 1 1 d D U . . . C13 C 0.7772(7) 0.6568(8) 0.2080(3) 0.0278(13) Uani 1 1 d D U . . . C10 C 0.4862(7) 0.5862(8) 0.1675(3) 0.0315(14) Uani 1 1 d D U . . . C12 C 0.7497(7) 0.5419(8) 0.1590(3) 0.0290(13) Uani 1 1 d D U . . . C11 C 0.6021(6) 0.5037(9) 0.1410(3) 0.0324(14) Uani 1 1 d D U . . . H11 H 0.580586 0.422113 0.110970 0.039 Uiso 1 1 calc R . . . . C27 C 0.7093(7) 0.1760(10) 0.2930(4) 0.0439(17) Uani 1 1 d D U . . . H27 H 0.674303 0.245699 0.260008 0.053 Uiso 1 1 calc R . . . . C15 C 0.5195(9) 0.7115(9) 0.2114(3) 0.0323(13) Uani 1 1 d D U . . . C14 C 0.6606(8) 0.7419(9) 0.2326(4) 0.0322(14) Uani 1 1 d D U . . . H14 H 0.680916 0.820762 0.264013 0.039 Uiso 1 1 calc R . . . . C32 C 0.6107(10) 0.1213(11) 0.3375(4) 0.0513(18) Uani 1 1 d D U . . . H32 H 0.512798 0.155348 0.334387 0.062 Uiso 1 1 calc R . . . . C6 C 0.5405(9) 0.6282(12) 0.4302(3) 0.0499(16) Uani 1 1 d D U . . . C9 C 0.3582(10) 0.8101(11) 0.2923(4) 0.0340(17) Uani 1 1 d . U . . . C7 C 0.4030(8) 0.6832(11) 0.3968(4) 0.0460(18) Uani 1 1 d D U . . . H7 H 0.380153 0.790059 0.412894 0.055 Uiso 1 1 calc R . . . . C26 C 0.9642(8) 0.1870(11) 0.2511(4) 0.0386(16) Uani 1 1 d D U . . . H26 H 0.992337 0.097560 0.223715 0.046 Uiso 1 1 calc R . . . . C23 C 0.8857(17) 0.5279(13) 0.0587(5) 0.068(3) Uani 1 1 d D U . . . H23A H 0.973671 0.475279 0.045114 0.081 Uiso 1 1 calc R . . . . H23B H 0.803181 0.491404 0.029660 0.081 Uiso 1 1 calc R . . . . C1 C 0.5786(12) 0.6743(13) 0.4950(4) 0.058(2) Uani 1 1 d D U . . . H1 H 0.517143 0.743539 0.516003 0.069 Uiso 1 1 calc R . . . . C29 C 0.9026(12) 0.0220(10) 0.3456(4) 0.0444(16) Uani 1 1 d D U . . . H29 H 1.000462 -0.012320 0.348980 0.053 Uiso 1 1 calc R . . . . C5 C 0.6363(11) 0.5219(13) 0.4019(5) 0.060(2) Uani 1 1 d D U . . . H5 H 0.612376 0.487945 0.359124 0.072 Uiso 1 1 calc R . . . . C2 C 0.7080(12) 0.6173(16) 0.5287(5) 0.068(2) Uani 1 1 d D U . . . H2 H 0.729781 0.647648 0.572026 0.081 Uiso 1 1 calc R . . . . C31 C 0.6616(10) 0.0147(11) 0.3869(4) 0.0513(18) Uani 1 1 d D U . . . H31 H 0.598265 -0.021694 0.417415 0.062 Uiso 1 1 calc R . . . . C30 C 0.8088(9) -0.0366(12) 0.3897(5) 0.0509(18) Uani 1 1 d D U . . . H30 H 0.843150 -0.110090 0.421390 0.061 Uiso 1 1 calc R . . . . C3 C 0.8053(15) 0.5159(17) 0.4986(5) 0.074(2) Uani 1 1 d D U . . . H3 H 0.893743 0.483696 0.520619 0.089 Uiso 1 1 calc R . . . . C25 C 1.0973(10) 0.2582(13) 0.2826(6) 0.055(2) Uani 1 1 d D U . . . H25A H 1.160244 0.293678 0.249727 0.083 Uiso 1 1 calc GR . . . . H25B H 1.148734 0.180281 0.310143 0.083 Uiso 1 1 calc GR . . . . H25C H 1.070946 0.347739 0.308663 0.083 Uiso 1 1 calc GR . . . . C8 C 0.2776(13) 0.5787(16) 0.4047(6) 0.068(3) Uani 1 1 d D U . . . H8A H 0.194035 0.615276 0.377182 0.102 Uiso 1 1 calc GR . . . . H8B H 0.253727 0.580055 0.449620 0.102 Uiso 1 1 calc GR . . . . H8C H 0.302281 0.471733 0.392475 0.102 Uiso 1 1 calc GR . . . . C16 C 0.3339(18) 0.930(2) 0.1850(7) 0.077(3) Uani 1 1 d . U . . . H16A H 0.327828 1.031268 0.207823 0.092 Uiso 1 1 calc R . . . . H16B H 0.233580 0.895563 0.172612 0.092 Uiso 1 1 calc R . . . . C4 C 0.7665(13) 0.4641(16) 0.4346(5) 0.071(2) Uani 1 1 d D U . . . H4 H 0.826288 0.392191 0.414120 0.086 Uiso 1 1 calc R . . . . C22 C 0.9027(16) 0.6981(13) 0.0482(7) 0.083(3) Uani 1 1 d D U . . . H22A H 0.957858 0.714236 0.009890 0.099 Uiso 1 1 calc R . . . . H22B H 0.960270 0.743378 0.085602 0.099 Uiso 1 1 calc R . . . . C19 C 0.6100(18) 1.036(2) 0.0524(7) 0.100(3) Uani 1 1 d D U . . . H19A H 0.539399 0.985739 0.020709 0.120 Uiso 1 1 calc R . . . . H19B H 0.622924 1.145828 0.039370 0.120 Uiso 1 1 calc R . . . . C18 C 0.5542(17) 1.030(2) 0.1170(7) 0.098(3) Uani 1 1 d D U . . . H18A H 0.626426 0.973381 0.145740 0.118 Uiso 1 1 calc R . . . . H18B H 0.550124 1.138793 0.133078 0.118 Uiso 1 1 calc R . . . . C21 C 0.7632(17) 0.7833(16) 0.0391(9) 0.099(3) Uani 1 1 d D U . . . H21A H 0.727672 0.768990 -0.006459 0.119 Uiso 1 1 calc R . . . . H21B H 0.693955 0.728006 0.065099 0.119 Uiso 1 1 calc R . . . . C20 C 0.7502(18) 0.9521(17) 0.0534(10) 0.106(3) Uani 1 1 d D U . . . H20A H 0.798738 0.968422 0.096741 0.127 Uiso 1 1 calc R . . . . H20B H 0.809287 1.008075 0.023002 0.127 Uiso 1 1 calc R . . . . C17 C 0.4112(16) 0.957(2) 0.1241(9) 0.093(3) Uani 1 1 d D U . . . H17A H 0.416829 0.852597 0.104022 0.111 Uiso 1 1 calc R . . . . H17B H 0.342111 1.018481 0.095646 0.111 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 Br2 0.0268(5) 0.0569(6) 0.0581(6) -0.0169(5) -0.0110(4) 0.0039(4) Br1 0.0292(6) 0.0956(9) 0.0627(7) -0.0150(6) 0.0017(5) -0.0184(5) O2 0.047(4) 0.040(3) 0.035(3) 0.009(3) 0.009(3) 0.015(3) O1 0.040(4) 0.052(4) 0.050(4) -0.008(3) 0.014(3) 0.011(3) O3 0.051(4) 0.045(3) 0.029(3) -0.001(3) 0.003(3) 0.006(3) O4 0.048(4) 0.062(4) 0.051(4) 0.004(3) 0.015(3) 0.022(4) N1 0.040(4) 0.038(4) 0.027(3) 0.002(3) 0.005(3) 0.003(3) N2 0.030(4) 0.047(4) 0.035(3) 0.002(3) -0.001(3) 0.013(3) C24 0.027(4) 0.031(4) 0.034(4) -0.007(3) 0.005(3) -0.002(3) C28 0.044(3) 0.029(3) 0.041(3) -0.003(3) 0.002(3) 0.001(3) C13 0.024(3) 0.032(3) 0.026(3) -0.003(2) -0.005(2) 0.000(2) C10 0.025(3) 0.041(3) 0.028(3) 0.001(3) 0.001(3) -0.007(3) C12 0.031(3) 0.030(3) 0.025(3) 0.001(2) -0.001(2) 0.003(3) C11 0.033(3) 0.036(3) 0.029(3) 0.001(3) 0.000(3) -0.001(3) C27 0.047(4) 0.035(3) 0.050(3) 0.002(3) 0.005(3) -0.001(3) C15 0.030(3) 0.039(3) 0.028(3) 0.002(3) -0.001(2) 0.004(3) C14 0.030(3) 0.036(3) 0.029(3) -0.005(2) -0.005(3) 0.005(2) C32 0.056(4) 0.044(3) 0.055(4) 0.000(3) 0.010(3) -0.006(3) C6 0.064(4) 0.051(3) 0.033(3) -0.001(3) -0.002(3) -0.002(3) C9 0.028(5) 0.038(4) 0.036(4) 0.002(3) 0.002(3) 0.001(3) C7 0.059(4) 0.050(4) 0.029(3) -0.004(3) 0.003(3) -0.005(4) C26 0.041(4) 0.031(3) 0.044(3) -0.001(3) 0.002(3) 0.010(3) C23 0.090(7) 0.074(6) 0.041(4) 0.020(4) 0.020(4) 0.009(5) C1 0.073(5) 0.062(4) 0.037(3) 0.000(3) -0.009(3) -0.002(4) C29 0.055(4) 0.037(3) 0.040(3) 0.000(3) -0.001(3) -0.001(3) C5 0.071(5) 0.065(4) 0.043(4) -0.003(3) -0.008(3) 0.007(4) C2 0.080(5) 0.075(5) 0.045(4) 0.001(4) -0.020(4) 0.000(4) C31 0.061(4) 0.046(3) 0.048(4) 0.000(3) 0.009(3) -0.010(3) C30 0.064(4) 0.044(3) 0.045(3) 0.002(3) 0.003(3) -0.004(3) C3 0.081(5) 0.081(5) 0.056(4) 0.002(4) -0.022(4) 0.006(4) C25 0.047(6) 0.051(5) 0.066(6) 0.007(4) -0.008(5) 0.001(4) C8 0.064(7) 0.089(7) 0.051(5) 0.017(5) -0.001(5) -0.015(6) C16 0.075(7) 0.091(7) 0.066(6) 0.035(5) 0.013(5) 0.040(5) C4 0.078(5) 0.077(5) 0.055(4) -0.001(4) -0.014(4) 0.010(4) C22 0.104(6) 0.085(5) 0.061(4) 0.025(5) 0.019(5) 0.007(5) C19 0.109(6) 0.101(6) 0.092(5) 0.030(5) 0.018(5) 0.023(5) C18 0.103(6) 0.099(6) 0.094(5) 0.032(5) 0.014(5) 0.029(5) C21 0.118(6) 0.099(6) 0.082(5) 0.026(5) 0.021(5) 0.009(5) C20 0.119(6) 0.107(6) 0.093(5) 0.023(5) 0.021(5) 0.017(5) C17 0.093(6) 0.100(6) 0.086(5) 0.035(5) 0.015(5) 0.037(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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C24 O2 C26 119.0(6) . . ? C9 O3 C7 117.5(7) . . ? C24 N1 C12 119.7(6) . . ? C24 N1 C23 120.7(8) . . ? C12 N1 C23 119.3(8) . . ? C15 N2 C16 121.2(8) . . ? C9 N2 C15 121.0(7) . . ? C9 N2 C16 117.7(8) . . ? O2 C24 N1 109.0(6) . . ? O1 C24 O2 125.9(8) . . ? O1 C24 N1 125.1(8) . . ? C27 C28 C26 124.4(6) . . ? C27 C28 C29 115.5(7) . . ? C29 C28 C26 120.1(7) . . ? C12 C13 Br2 119.8(4) . . ? C12 C13 C14 120.5(7) . . ? C14 C13 Br2 119.6(5) . . ? C11 C10 Br1 118.0(4) . . ? C11 C10 C15 119.1(7) . . ? C15 C10 Br1 122.8(5) . . ? N1 C12 C13 123.2(6) . . ? N1 C12 C11 119.1(5) . . ? C11 C12 C13 117.5(6) . . ? C12 C11 C10 121.1(6) . . ? C32 C27 C28 123.0(7) . . ? C10 C15 N2 119.4(7) . . ? C14 C15 N2 120.3(6) . . ? C14 C15 C10 120.3(7) . . ? C15 C14 C13 121.0(7) . . ? C27 C32 C31 119.1(8) . . ? C1 C6 C7 120.2(7) . . ? C5 C6 C7 123.0(7) . . ? C5 C6 C1 116.8(8) . . ? O3 C9 N2 110.9(7) . . ? O4 C9 O3 123.9(8) . . ? O4 C9 N2 125.2(8) . . ? O3 C7 C6 106.0(6) . . ? O3 C7 C8 109.6(8) . . ? C6 C7 C8 114.1(9) . . ? C28 C26 O2 106.2(6) . . ? C25 C26 O2 109.0(7) . . ? C25 C26 C28 114.8(8) . . ? C22 C23 N1 118.5(10) . . ? C2 C1 C6 120.8(9) . . ? C30 C29 C28 123.4(8) . . ? C4 C5 C6 123.3(9) . . ? C1 C2 C3 121.6(10) . . ? C30 C31 C32 119.2(9) . . ? C29 C30 C31 119.9(9) . . ? C2 C3 C4 118.4(11) . . ? N2 C16 C17 115.3(11) . . ? C5 C4 C3 119.1(10) . . ? C23 C22 C21 113.5(13) . . ? C20 C19 C18 109.6(14) . . ? C17 C18 C19 118.7(15) . . ? C20 C21 C22 122.3(14) . . ? C19 C20 C21 123.4(16) . . ? C18 C17 C16 128.8(15) . . ? 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 Br2 C13 1.880(7) . ? Br1 C10 1.860(7) . ? O2 C24 1.333(10) . ? O2 C26 1.463(10) . ? O1 C24 1.202(10) . ? O3 C9 1.356(11) . ? O3 C7 1.446(10) . ? O4 C9 1.208(11) . ? N1 C24 1.379(11) . ? N1 C12 1.398(9) . ? N1 C23 1.467(11) . ? N2 C15 1.434(10) . ? N2 C9 1.360(11) . ? N2 C16 1.454(13) . ? C28 C27 1.400(3) . ? C28 C26 1.453(3) . ? C28 C29 1.401(3) . ? C13 C12 1.398(3) . ? C13 C14 1.399(3) . ? C10 C11 1.398(3) . ? C10 C15 1.399(3) . ? C12 C11 1.398(3) . ? C27 C32 1.400(3) . ? C15 C14 1.345(12) . ? C32 C31 1.400(3) . ? C6 C7 1.452(3) . ? C6 C1 1.399(3) . ? C6 C5 1.399(3) . ? C7 C8 1.452(3) . ? C26 C25 1.453(3) . ? C23 C22 1.450(3) . ? C1 C2 1.399(3) . ? C29 C30 1.375(14) . ? C5 C4 1.399(3) . ? C2 C3 1.399(3) . ? C31 C30 1.399(3) . ? C3 C4 1.399(3) . ? C16 C17 1.49(2) . ? C22 C21 1.452(3) . ? C19 C18 1.451(3) . ? C19 C20 1.449(3) . ? C18 C17 1.449(2) . ? C21 C20 1.449(3) . ?