#------------------------------------------------------------------------------ #$Date: 2021-08-13 01:23:18 +0300 (Fri, 13 Aug 2021) $ #$Revision: 268055 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/56/43/1564356.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_1564356 loop_ _publ_author_name 'Lai, Zhenzhen' 'Li, Aimin' 'Peng, Sangshan' 'Sessler, Jonathan L.' 'He, Qing' _publ_section_title ; Trimacrocyclic hexasubstituted benzene linked by labile octahedral [X(CHCl3)6]-- clusters ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D1SC03713G _journal_year 2021 _chemical_formula_moiety '2(C66 H66 O18), 2(C1 H6 N3), 6(C H Br3), 0.552(Br1), 0.448(Cl)' _chemical_formula_sum 'C140 H150 Br18.56 Cl0.44 N6 O36' _chemical_formula_weight 3991.23 _space_group_crystal_system trigonal _space_group_IT_number 148 _space_group_name_Hall '-R 3' _space_group_name_H-M_alt 'R -3 :H' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2021-06-07 _audit_creation_method ; Olex2 1.3 (compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272) ; _audit_update_record ; 2021-06-07 deposited with the CCDC. 2021-08-11 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 120 _cell_formula_units_Z 3 _cell_length_a 21.83560(10) _cell_length_b 21.83560(10) _cell_length_c 27.6959(2) _cell_measurement_reflns_used 20718 _cell_measurement_temperature 100.0(4) _cell_measurement_theta_max 75.6840 _cell_measurement_theta_min 2.8100 _cell_volume 11436.06(11) _computing_cell_refinement 'CrysAlisPro 1.171.41.64a (Rigaku OD, 2020)' _computing_data_collection 'CrysAlisPro 1.171.41.64a (Rigaku OD, 2020)' _computing_data_reduction 'CrysAlisPro 1.171.41.64a (Rigaku OD, 2020)' _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 2018/2 (Sheldrick, 2018)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 100.0(4) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 10.0000 _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.988 _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 87.00 113.00 0.50 0.10 -- 111.82 61.00 30.00 52 2 \w 83.00 173.00 0.50 0.10 -- 111.82 62.00 112.00 180 3 \w 137.00 163.00 0.50 0.10 -- 111.82 61.00 30.00 52 4 \w 95.00 165.00 0.50 0.10 -- 111.82 61.00 -90.00 140 5 \w 145.00 171.00 0.50 0.10 -- 111.82 61.00-150.00 52 6 \w 91.00 142.00 0.50 0.10 -- 111.82 61.00-150.00 102 7 \w 70.00 99.00 0.50 0.10 -- 111.82 -94.00 30.00 58 8 \w 50.00 85.00 0.50 0.10 -- 111.82-163.00 112.00 70 9 \w 37.00 79.00 0.50 0.10 -- 111.82-103.00 162.00 84 10 \w 106.00 138.00 0.50 0.10 -- 111.82-163.00 112.00 64 11 \w 83.00 119.00 0.50 0.10 -- 111.82-142.00-172.00 72 12 \w 51.00 97.00 0.50 0.10 -- 111.82 -77.00 30.00 92 13 \w 39.00 67.00 0.50 0.10 -- 111.82 -61.00 60.00 56 14 \w 38.00 67.00 0.50 0.10 -- 111.82 -62.00 -25.00 58 15 \w 38.00 63.00 0.50 0.10 -- 111.82 -61.00 30.00 50 16 \w 39.00 65.00 0.50 0.10 -- 111.82 -61.00 -60.00 52 17 \w 39.00 67.00 0.50 0.10 -- 111.82 -61.00 -90.00 56 18 \w 43.00 98.00 0.50 0.10 -- 111.82 -77.00-120.00 110 19 \w 39.00 68.00 0.50 0.10 -- 111.82 -61.00-120.00 58 20 \w 90.00 173.00 0.50 0.10 -- 111.82 111.00 0.00 166 21 \w 135.00 161.00 0.50 0.10 -- 111.82 128.00 73.00 52 22 \w 96.00 122.00 0.50 0.10 -- 111.82 128.00 73.00 52 23 \w -29.00 15.00 0.50 0.05 -- -39.20 19.00-150.00 88 24 \w -26.00 8.00 0.50 0.10 -- -62.00 21.00 -92.00 68 25 \w -18.00 8.00 0.50 0.10 -- -62.00 15.00 90.00 52 26 \w -88.00 17.00 0.50 0.05 -- -39.20 -21.00 100.00 210 27 \w -123.00 -88.00 0.50 0.10 -- -62.00 -94.00 120.00 70 28 \w -125.00 -48.00 0.50 0.05 -- -39.20-179.00 120.00 154 29 \w -124.00 -50.00 0.50 0.05 -- -39.20-179.00 0.00 148 30 \w -138.00-107.00 0.50 0.10 -- -62.00-128.00 -1.00 62 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'ROD, Synergy Custom DW system, HyPix' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0656199000 _diffrn_orient_matrix_UB_12 -0.0227015000 _diffrn_orient_matrix_UB_13 0.0320250000 _diffrn_orient_matrix_UB_21 -0.0427638000 _diffrn_orient_matrix_UB_22 -0.0015968000 _diffrn_orient_matrix_UB_23 -0.0447011000 _diffrn_orient_matrix_UB_31 -0.0225089000 _diffrn_orient_matrix_UB_32 -0.0781950000 _diffrn_orient_matrix_UB_33 -0.0083705000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0464 _diffrn_reflns_av_unetI/netI 0.0235 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.988 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_number 23902 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.988 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 75.860 _diffrn_reflns_theta_min 2.829 _diffrn_source 'Rotating-anode X-ray tube' _diffrn_source_type 'Rigaku (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 6.464 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.29326 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.41.64a (Rigaku Oxford Diffraction, 2020) 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 1.739 _exptl_crystal_description cube _exptl_crystal_F_000 5931 _exptl_crystal_size_max 0.102 _exptl_crystal_size_mid 0.084 _exptl_crystal_size_min 0.065 _refine_diff_density_max 1.760 _refine_diff_density_min -1.727 _refine_diff_density_rms 0.172 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.178 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 354 _refine_ls_number_reflns 5245 _refine_ls_number_restraints 33 _refine_ls_restrained_S_all 1.229 _refine_ls_R_factor_all 0.0851 _refine_ls_R_factor_gt 0.0848 _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^)+(0.0537P)^2^+440.2679P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1964 _refine_ls_wR_factor_ref 0.1965 _reflns_Friedel_coverage 0.000 _reflns_number_gt 5205 _reflns_number_total 5245 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1sc03713g2.cif _cod_data_source_block lzz-1-100k _cod_original_cell_volume 11436.05(13) _cod_original_sg_symbol_H-M 'R -3' _cod_database_code 1564356 _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 0.679 _shelx_estimated_absorpt_t_min 0.559 _reflns_odcompleteness_completeness 99.85 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 68.13 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H,H) groups 2. Restrained distances Br2-C24 \\sim Br2A-C24 with sigma of 0.02 Br4-C24 \\sim Br4A-C24 with sigma of 0.02 Br3-C24 \\sim Br3A-C24 with sigma of 0.02 3. Uiso/Uaniso restraints and constraints Uanis(O3A) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002 Uanis(Br2A) \\sim Ueq, Uanis(Br3A) \\sim Ueq: with sigma of 0.0001 and sigma for terminal atoms of 0.0002 Uanis(Br4A) \\sim Ueq, Uanis(Br4) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002 4. Rigid body (RIGU) restrains Br2A, Br3A with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002 5. Others Sof(H24A)=Sof(Br2A)=Sof(Br3A)=Sof(Br4A)=1-FVAR(1) Sof(H24)=Sof(Br2)=Sof(Br3)=Sof(Br4)=FVAR(1) Sof(H11C)=Sof(H11D)=Sof(C12A)=Sof(H12C)=Sof(H12D)=1-FVAR(2) Sof(H11A)=Sof(H11B)=Sof(C12)=Sof(H12A)=Sof(H12B)=FVAR(2) Sof(Cl1)=0.16667*(1-FVAR(4)) Sof(Br1)=0.16667*FVAR(4) Sof(H10C)=Sof(H10D)=Sof(O00B)=1-FVAR(4) Sof(H10A)=Sof(H10B)=Sof(O3A)=FVAR(4) 6.a Ternary CH refined with riding coordinates: C24(H24), C24(H24A) 6.b Secondary CH2 refined with riding coordinates: C2(H2A,H2B), C9(H9A,H9B), C10(H10A,H10B), C10(H10C,H10D), C11(H11A,H11B), C11(H11C,H11D), C14(H14A,H14B), C21(H21A,H21B), C12(H12A,H12B), C12A(H12C,H12D) 6.c Aromatic/amide H refined with riding coordinates: C4(H4), C5(H5), C6(H6), C7(H7), C16(H16), C17(H17), C18(H18), C19(H19) 6.d X=CH2 refined with riding coordinates: N1(H1A,H1B) ; _shelx_res_file ; TITL lzz-1-100k_a.res in R-3 lzz-1-100k.res created by SHELXL-2018/3 at 22:42:56 on 07-Jun-2021 REM Old TITL lzz-1-100k_a.res in R-3 REM SHELXT solution in R-3: R1 0.244, Rweak 0.038, Alpha 0.055 REM 0.000 for 0 systematic absences, Orientation as input REM Formula found by SHELXT: C146 Br19 N6 O30 CELL 1.54184 21.8356 21.8356 27.6959 90 90 120 ZERR 3 0.0001 0.0001 0.0002 0 0 0 LATT 3 SYMM -Y,+X-Y,+Z SYMM +Y-X,-X,+Z SFAC C H Br Cl N O UNIT 420 450 55.67 1.33 18 108 SADI Br2 C24 Br2A C24 RIGU 0.001 0.002 Br2A Br3A ISOR 0.001 0.002 O3A SADI Br4 C24 Br4A C24 ISOR 0.0001 0.0002 Br2A Br3A SADI Br3 C24 Br3A C24 ISOR 0.001 0.002 Br4A Br4 L.S. 4 0 0 PLAN 6 SIZE 0.102 0.084 0.065 TEMP -173 CONF list 4 MORE -1 BOND $H fmap 2 53 acta REM REM REM WGHT 0.053700 440.267883 FVAR 0.13020 0.82980 0.57957 0.55239 0.37103 O1 6 0.347066 0.517796 0.202926 11.00000 0.01563 0.00589 = 0.01335 0.00252 0.00132 0.00817 O2 6 0.432775 0.473593 0.240644 11.00000 0.01445 0.00904 = 0.02255 0.00219 -0.00485 0.00792 O4 6 0.497433 0.853334 0.408056 11.00000 0.01699 0.03448 = 0.03860 0.01929 0.00478 0.01315 O5 6 0.535850 0.751162 0.382500 11.00000 0.01429 0.02330 = 0.02113 -0.00837 0.00747 0.00335 O6 6 0.490858 0.690004 0.300880 11.00000 0.00539 0.01359 = 0.00811 -0.00373 -0.00203 0.00305 N1 5 0.381124 0.645888 0.380125 11.00000 0.04857 0.05189 = 0.07257 0.00114 0.00776 0.02581 AFIX 93 H1A 2 0.426245 0.677428 0.383344 11.00000 -1.20000 H1B 2 0.367590 0.600616 0.378523 11.00000 -1.20000 AFIX 0 C1 1 0.334001 0.602950 0.249132 11.00000 0.01031 0.00702 = 0.01325 -0.00192 -0.00170 0.00664 C2 1 0.334409 0.533623 0.251078 11.00000 0.00787 0.00549 = 0.01404 0.00139 0.00061 0.00440 AFIX 23 H2A 2 0.372066 0.537968 0.273130 11.00000 -1.20000 H2B 2 0.288387 0.495310 0.263111 11.00000 -1.20000 AFIX 0 C3 1 0.330993 0.448289 0.196071 11.00000 0.01472 0.00493 = 0.00713 0.00269 0.00282 0.00529 C4 1 0.271700 0.402921 0.169898 11.00000 0.01504 0.01328 = 0.00691 0.00214 0.00171 0.00758 AFIX 43 H4 2 0.240159 0.418203 0.159248 11.00000 -1.20000 AFIX 0 C5 1 0.257713 0.334986 0.158971 11.00000 0.02443 0.01631 = 0.00682 -0.00128 0.00009 0.00649 AFIX 43 H5 2 0.217054 0.304011 0.140656 11.00000 -1.20000 AFIX 0 C6 1 0.303700 0.312804 0.175064 11.00000 0.02967 0.00945 = 0.02353 -0.00158 0.00413 0.01169 AFIX 43 H6 2 0.294627 0.266611 0.167345 11.00000 -1.20000 AFIX 0 C7 1 0.363214 0.357746 0.202509 11.00000 0.02231 0.01227 = 0.02179 -0.00011 0.00307 0.01388 AFIX 43 H7 2 0.394371 0.342152 0.213465 11.00000 -1.20000 AFIX 0 C8 1 0.376588 0.425699 0.213723 11.00000 0.01189 0.00413 = 0.01488 0.00035 0.00164 0.00306 C9 1 0.466954 0.447154 0.271533 11.00000 0.01365 0.01734 = 0.02311 0.00568 -0.00005 0.00987 AFIX 23 H9A 2 0.502575 0.441275 0.253164 11.00000 -1.20000 H9B 2 0.431842 0.400691 0.285082 11.00000 -1.20000 AFIX 0 C10 1 0.502034 0.500228 0.311385 11.00000 0.00591 0.01738 = 0.02495 0.00786 0.00222 0.00388 PART 1 AFIX 23 H10A 2 0.523788 0.482430 0.334752 51.00000 -1.20000 H10B 2 0.539930 0.545264 0.297777 51.00000 -1.20000 AFIX 23 PART 2 H10C 2 0.538877 0.493426 0.327179 -51.00000 -1.20000 H10D 2 0.524513 0.548920 0.298336 -51.00000 -1.20000 AFIX 0 PART 0 C11 1 0.474119 0.543564 0.380928 11.00000 0.01710 0.02465 = 0.02720 -0.00612 -0.00034 0.00645 PART 1 AFIX 23 H11A 2 0.492880 0.595006 0.377192 31.00000 -1.20000 H11B 2 0.513964 0.537218 0.391355 31.00000 -1.20000 AFIX 23 PART 2 H11C 2 0.513990 0.586047 0.366073 -31.00000 -1.20000 H11D 2 0.493959 0.528769 0.407659 -31.00000 -1.20000 AFIX 0 PART 0 C13 1 0.505320 0.809544 0.441727 11.00000 0.07427 0.04053 = 0.02052 0.00623 0.01425 0.04450 C14 1 0.560912 0.793246 0.425017 11.00000 0.05791 0.02662 = 0.00828 -0.00599 -0.00815 0.03025 AFIX 23 H14A 2 0.605428 0.837659 0.418030 11.00000 -1.20000 H14B 2 0.570440 0.767291 0.450490 11.00000 -1.20000 AFIX 0 C15 1 0.583854 0.740192 0.356938 11.00000 0.00955 0.00893 = 0.01131 0.00016 0.00118 -0.00034 C16 1 0.650072 0.757395 0.372149 11.00000 0.02114 0.01135 = 0.01098 -0.00278 -0.01104 0.00442 AFIX 43 H16 2 0.666728 0.779367 0.402670 11.00000 -1.20000 AFIX 0 C17 1 0.693402 0.742757 0.342926 11.00000 0.01304 0.01784 = 0.02227 -0.00130 -0.00952 0.00981 AFIX 43 H17 2 0.739425 0.754798 0.353618 11.00000 -1.20000 AFIX 0 C18 1 0.669627 0.711143 0.298990 11.00000 0.01233 0.01774 = 0.02629 -0.00415 -0.00325 0.01037 AFIX 43 H18 2 0.699251 0.701138 0.279379 11.00000 -1.20000 AFIX 0 C19 1 0.602333 0.693420 0.282651 11.00000 0.00990 0.01088 = 0.01307 -0.00338 -0.00238 0.00557 AFIX 43 H19 2 0.586436 0.672015 0.251890 11.00000 -1.20000 AFIX 0 C20 1 0.558636 0.707238 0.311609 11.00000 0.00507 0.00473 = 0.01017 0.00152 -0.00142 0.00093 C21 1 0.467297 0.668457 0.251752 11.00000 0.00573 0.01177 = 0.00794 -0.00803 -0.00363 0.00747 AFIX 23 H21A 2 0.460897 0.621051 0.245123 11.00000 -1.20000 H21B 2 0.501808 0.702644 0.228422 11.00000 -1.20000 AFIX 0 C22 1 0.397512 0.667180 0.248547 11.00000 0.00399 0.00712 = 0.00856 -0.00276 -0.00270 0.00356 C23 1 0.333333 0.666667 0.377681 10.33333 0.04640 0.04640 = 0.04470 0.00000 0.00000 0.02320 C24 1 0.561841 0.371805 0.411002 11.00000 0.02022 0.01034 = 0.02444 0.00151 -0.00226 0.00229 PART 1 AFIX 13 H24 2 0.576973 0.346498 0.388084 21.00000 -1.20000 AFIX 13 PART 2 H24A 2 0.602991 0.378707 0.391050 -21.00000 -1.20000 AFIX 0 PART 1 BR1 3 0.666667 0.333333 0.333333 40.16667 0.03315 0.03315 = 0.03317 0.00000 0.00000 0.01657 BR2 3 0.468478 0.351742 0.391615 21.00000 0.01888 0.02418 = 0.02564 0.00642 0.00217 0.00164 BR3 3 0.558020 0.334238 0.474551 21.00000 0.04606 0.03985 = 0.03455 0.02157 0.00432 0.02336 BR4 3 0.629277 0.469695 0.406997 21.00000 0.03226 0.01603 = 0.05325 0.00819 -0.01456 -0.00086 O3A 6 0.451843 0.511989 0.335101 51.00000 0.01641 0.01625 = 0.01618 -0.00016 0.00012 0.00813 C12 1 0.483392 0.901684 0.422550 31.00000 0.02763 0.02230 = 0.01973 -0.00188 0.00226 0.01434 AFIX 23 H12A 2 0.526625 0.941438 0.436759 31.00000 -1.20000 H12B 2 0.446968 0.881647 0.448186 31.00000 -1.20000 AFIX 0 PART 2 BR2A 3 0.483645 0.335505 0.367781 -21.00000 0.05609 0.05602 = 0.05613 0.00003 -0.00017 0.02802 BR3A 3 0.549866 0.306156 0.456834 -21.00000 0.04284 0.04279 = 0.04280 0.00017 -0.00006 0.02142 BR4A 3 0.587045 0.466347 0.434523 -21.00000 0.04669 0.03377 = 0.03952 -0.00701 -0.01476 0.02328 CL1 4 0.666667 0.333333 0.333333 -40.16667 0.00201 0.00201 = 0.00954 0.00000 0.00000 0.00101 O00B 6 0.447199 0.488787 0.345695 -51.00000 0.00925 0.01632 = 0.02326 -0.00364 0.00328 0.00243 C12A 1 0.435233 0.861542 0.402059 -31.00000 0.01354 0.03595 = 0.02451 0.00954 -0.00279 0.00935 AFIX 23 H12C 2 0.400403 0.823704 0.380777 -31.00000 -1.20000 H12D 2 0.412639 0.857361 0.433812 -31.00000 -1.20000 AFIX 0 HKLF 4 REM lzz-1-100k_a.res in R-3 REM wR2 = 0.1965, GooF = S = 1.178, Restrained GooF = 1.229 for all data REM R1 = 0.0848 for 5205 Fo > 4sig(Fo) and 0.0851 for all 5245 data REM 354 parameters refined using 33 restraints END WGHT 0.0536 441.3442 REM Highest difference peak 1.760, deepest hole -1.727, 1-sigma level 0.172 Q1 1 0.6098 0.4849 0.4271 11.00000 0.05 1.76 Q2 1 0.5654 0.4566 0.4523 11.00000 0.05 1.72 Q3 1 0.5047 0.3375 0.3493 11.00000 0.05 1.22 Q4 1 0.5445 0.4642 0.4719 11.00000 0.05 0.90 Q5 1 0.5375 0.8363 0.4736 11.00000 0.05 0.79 Q6 1 0.4720 0.7673 0.4629 11.00000 0.05 0.70 ; _shelx_res_checksum 61952 _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 2.272 _oxdiff_exptl_absorpt_empirical_full_min 0.371 loop_ _space_group_symop_operation_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' 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 O1 O 0.3471(2) 0.51780(19) 0.20293(14) 0.0104(8) Uani 1 1 d . . . . . O2 O 0.4328(2) 0.4736(2) 0.24064(15) 0.0144(8) Uani 1 1 d . . . . . O4 O 0.4974(2) 0.8533(3) 0.40806(19) 0.0299(11) Uani 1 1 d . . . . . O5 O 0.5358(2) 0.7512(2) 0.38250(16) 0.0223(10) Uani 1 1 d . . . . . O6 O 0.49086(19) 0.6900(2) 0.30088(13) 0.0098(7) Uani 1 1 d . . . . . N1 N 0.3811(5) 0.6459(5) 0.3801(3) 0.057(2) Uani 1 1 d . . . . . H1A H 0.426245 0.677428 0.383344 0.069 Uiso 1 1 calc R U . . . H1B H 0.367590 0.600616 0.378523 0.069 Uiso 1 1 calc R U . . . C1 C 0.3340(3) 0.6030(3) 0.24913(19) 0.0092(10) Uani 1 1 d . . . . . C2 C 0.3344(3) 0.5336(3) 0.25108(19) 0.0087(10) Uani 1 1 d . . . . . H2A H 0.372066 0.537968 0.273130 0.010 Uiso 1 1 calc R U . . . H2B H 0.288387 0.495310 0.263111 0.010 Uiso 1 1 calc R U . . . C3 C 0.3310(3) 0.4483(3) 0.19607(19) 0.0088(10) Uani 1 1 d . . . . . C4 C 0.2717(3) 0.4029(3) 0.16990(19) 0.0115(10) Uani 1 1 d . . . . . H4 H 0.240159 0.418203 0.159248 0.014 Uiso 1 1 calc R U . . . C5 C 0.2577(3) 0.3350(3) 0.1590(2) 0.0175(12) Uani 1 1 d . . . . . H5 H 0.217054 0.304011 0.140656 0.021 Uiso 1 1 calc R U . . . C6 C 0.3037(4) 0.3128(3) 0.1751(2) 0.0200(13) Uani 1 1 d . . . . . H6 H 0.294627 0.266611 0.167345 0.024 Uiso 1 1 calc R U . . . C7 C 0.3632(3) 0.3577(3) 0.2025(2) 0.0165(12) Uani 1 1 d . . . . . H7 H 0.394371 0.342152 0.213465 0.020 Uiso 1 1 calc R U . . . C8 C 0.3766(3) 0.4257(3) 0.2137(2) 0.0107(10) Uani 1 1 d . . . . . C9 C 0.4670(3) 0.4472(3) 0.2715(2) 0.0171(12) Uani 1 1 d . . . . . H9A H 0.502575 0.441275 0.253164 0.021 Uiso 1 1 calc R U . . . H9B H 0.431842 0.400691 0.285082 0.021 Uiso 1 1 calc R U . . . C10 C 0.5020(3) 0.5002(3) 0.3114(2) 0.0169(12) Uani 1 1 d . . . . . H10A H 0.523788 0.482430 0.334752 0.020 Uiso 0.37(6) 1 calc R U P A 1 H10B H 0.539930 0.545264 0.297777 0.020 Uiso 0.37(6) 1 calc R U P A 1 H10C H 0.538877 0.493426 0.327179 0.020 Uiso 0.63(6) 1 calc R U P A 2 H10D H 0.524513 0.548920 0.298336 0.020 Uiso 0.63(6) 1 calc R U P A 2 C11 C 0.4741(3) 0.5436(4) 0.3809(3) 0.0248(14) Uani 1 1 d . . . . . H11A H 0.492880 0.595006 0.377192 0.030 Uiso 0.58(2) 1 calc R U P A 1 H11B H 0.513964 0.537218 0.391355 0.030 Uiso 0.58(2) 1 calc R U P A 1 H11C H 0.513990 0.586047 0.366073 0.030 Uiso 0.42(2) 1 calc R U P A 2 H11D H 0.493959 0.528769 0.407659 0.030 Uiso 0.42(2) 1 calc R U P A 2 C13 C 0.5053(5) 0.8095(4) 0.4417(3) 0.038(2) Uani 1 1 d . . . . . C14 C 0.5609(4) 0.7932(4) 0.4250(2) 0.0269(16) Uani 1 1 d . . . . . H14A H 0.605428 0.837659 0.418030 0.032 Uiso 1 1 calc R U . . . H14B H 0.570440 0.767291 0.450490 0.032 Uiso 1 1 calc R U . . . C15 C 0.5839(3) 0.7402(3) 0.3569(2) 0.0121(11) Uani 1 1 d . . . . . C16 C 0.6501(3) 0.7574(3) 0.3721(2) 0.0161(12) Uani 1 1 d . . . . . H16 H 0.666728 0.779367 0.402670 0.019 Uiso 1 1 calc R U . . . C17 C 0.6934(3) 0.7428(3) 0.3429(2) 0.0168(12) Uani 1 1 d . . . . . H17 H 0.739425 0.754798 0.353618 0.020 Uiso 1 1 calc R U . . . C18 C 0.6696(3) 0.7111(3) 0.2990(2) 0.0175(12) Uani 1 1 d . . . . . H18 H 0.699251 0.701138 0.279379 0.021 Uiso 1 1 calc R U . . . C19 C 0.6023(3) 0.6934(3) 0.2827(2) 0.0111(10) Uani 1 1 d . . . . . H19 H 0.586436 0.672015 0.251890 0.013 Uiso 1 1 calc R U . . . C20 C 0.5586(3) 0.7072(3) 0.31161(19) 0.0073(10) Uani 1 1 d . . . . . C21 C 0.4673(3) 0.6685(3) 0.25175(18) 0.0071(10) Uani 1 1 d . . . . . H21A H 0.460897 0.621051 0.245123 0.009 Uiso 1 1 calc R U . . . H21B H 0.501808 0.702644 0.228422 0.009 Uiso 1 1 calc R U . . . C22 C 0.3975(3) 0.6672(3) 0.24855(18) 0.0062(9) Uani 1 1 d . . . . . C23 C 0.333333 0.666667 0.3777(6) 0.046(4) Uani 1 3 d S T P . . C24 C 0.5618(3) 0.3718(3) 0.4110(2) 0.0207(13) Uani 1 1 d D . . . . H24 H 0.576973 0.346498 0.388084 0.025 Uiso 0.830(3) 1 calc R U P B 1 H24A H 0.602991 0.378707 0.391050 0.025 Uiso 0.170(3) 1 calc R U P B 2 Br1 Br 0.666667 0.333333 0.333333 0.033(6) Uani 0.55(3) 6 d S T P C 1 Br2 Br 0.46848(4) 0.35174(5) 0.39161(3) 0.0270(3) Uani 0.830(3) 1 d D . P B 1 Br3 Br 0.55802(6) 0.33424(7) 0.47455(5) 0.0393(3) Uani 0.830(3) 1 d D . P B 1 Br4 Br 0.62928(5) 0.46969(5) 0.40700(4) 0.0396(3) Uani 0.830(3) 1 d D U P B 1 O3A O 0.4518(9) 0.5120(18) 0.3351(8) 0.016(4) Uani 0.37(6) 1 d . U P A 1 C12 C 0.4834(6) 0.9017(6) 0.4226(4) 0.022(3) Uani 0.58(2) 1 d . . P A 1 H12A H 0.526625 0.941438 0.436759 0.027 Uiso 0.58(2) 1 calc R U P A 1 H12B H 0.446968 0.881647 0.448186 0.027 Uiso 0.58(2) 1 calc R U P A 1 Br2A Br 0.4836(4) 0.3355(4) 0.3678(3) 0.0561(17) Uani 0.170(3) 1 d D U P B 2 Br3A Br 0.5499(3) 0.3062(4) 0.4568(2) 0.0428(15) Uani 0.170(3) 1 d D U P B 2 Br4A Br 0.5870(3) 0.4663(3) 0.43452(19) 0.0386(15) Uani 0.170(3) 1 d D U P B 2 Cl1 Cl 0.666667 0.333333 0.333333 0.005(8) Uani 0.45(3) 6 d S T P C 2 O00B O 0.4472(4) 0.4888(12) 0.3457(6) 0.018(4) Uani 0.63(6) 1 d . . P A 2 C12A C 0.4352(8) 0.8615(9) 0.4021(6) 0.026(5) Uani 0.42(2) 1 d . . P A 2 H12C H 0.400403 0.823704 0.380777 0.031 Uiso 0.42(2) 1 calc R U P A 2 H12D H 0.412639 0.857361 0.433812 0.031 Uiso 0.42(2) 1 calc R U P A 2 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 O1 0.0156(19) 0.0059(17) 0.0133(19) 0.0025(14) 0.0013(15) 0.0082(15) O2 0.0144(19) 0.0090(18) 0.023(2) 0.0022(16) -0.0048(16) 0.0079(16) O4 0.017(2) 0.034(3) 0.039(3) 0.019(2) 0.005(2) 0.013(2) O5 0.014(2) 0.023(2) 0.021(2) -0.0084(18) 0.0075(17) 0.0033(18) O6 0.0054(17) 0.0136(18) 0.0081(18) -0.0037(14) -0.0020(14) 0.0031(14) N1 0.049(5) 0.052(5) 0.073(6) 0.001(4) 0.008(4) 0.026(4) C1 0.010(2) 0.007(2) 0.013(3) -0.0019(19) -0.002(2) 0.007(2) C2 0.008(2) 0.005(2) 0.014(3) 0.0014(19) 0.0006(19) 0.0044(19) C3 0.015(3) 0.005(2) 0.007(2) 0.0027(18) 0.0028(19) 0.005(2) C4 0.015(3) 0.013(3) 0.007(2) 0.002(2) 0.002(2) 0.008(2) C5 0.024(3) 0.016(3) 0.007(3) -0.001(2) 0.000(2) 0.006(2) C6 0.030(3) 0.009(3) 0.024(3) -0.002(2) 0.004(3) 0.012(3) C7 0.022(3) 0.012(3) 0.022(3) 0.000(2) 0.003(2) 0.014(2) C8 0.012(3) 0.004(2) 0.015(3) 0.0004(19) 0.002(2) 0.003(2) C9 0.014(3) 0.017(3) 0.023(3) 0.006(2) 0.000(2) 0.010(2) C10 0.006(2) 0.017(3) 0.025(3) 0.008(2) 0.002(2) 0.004(2) C11 0.017(3) 0.025(3) 0.027(3) -0.006(3) 0.000(3) 0.006(3) C13 0.074(6) 0.041(4) 0.021(3) 0.006(3) 0.014(4) 0.045(5) C14 0.058(5) 0.027(3) 0.008(3) -0.006(2) -0.008(3) 0.030(4) C15 0.010(2) 0.009(2) 0.011(3) 0.000(2) 0.001(2) 0.000(2) C16 0.021(3) 0.011(3) 0.011(3) -0.003(2) -0.011(2) 0.004(2) C17 0.013(3) 0.018(3) 0.022(3) -0.001(2) -0.010(2) 0.010(2) C18 0.012(3) 0.018(3) 0.026(3) -0.004(2) -0.003(2) 0.010(2) C19 0.010(2) 0.011(2) 0.013(3) -0.003(2) -0.002(2) 0.006(2) C20 0.005(2) 0.005(2) 0.010(2) 0.0015(18) -0.0014(19) 0.0009(18) C21 0.006(2) 0.012(2) 0.008(2) -0.0080(19) -0.0036(18) 0.007(2) C22 0.004(2) 0.007(2) 0.009(2) -0.0028(18) -0.0027(18) 0.0036(19) C23 0.046(5) 0.046(5) 0.045(9) 0.000 0.000 0.023(3) C24 0.020(3) 0.010(3) 0.024(3) 0.002(2) -0.002(2) 0.002(2) Br1 0.033(6) 0.033(6) 0.033(10) 0.000 0.000 0.017(3) Br2 0.0189(4) 0.0242(4) 0.0256(5) 0.0064(3) 0.0022(3) 0.0016(3) Br3 0.0461(6) 0.0398(6) 0.0346(6) 0.0216(5) 0.0043(5) 0.0234(5) Br4 0.0323(5) 0.0160(4) 0.0533(6) 0.0082(4) -0.0146(5) -0.0009(4) O3A 0.016(4) 0.016(5) 0.016(4) -0.0002(10) 0.0001(10) 0.008(2) C12 0.028(7) 0.022(6) 0.020(6) -0.002(4) 0.002(5) 0.014(5) Br2A 0.0561(17) 0.0560(17) 0.0561(18) 0.0000(2) -0.0002(2) 0.0280(9) Br3A 0.0428(16) 0.0428(16) 0.0428(16) 0.0002(2) -0.0001(2) 0.0214(8) Br4A 0.047(2) 0.0338(19) 0.040(2) -0.0070(14) -0.0148(15) 0.0233(15) Cl1 0.002(8) 0.002(8) 0.010(16) 0.000 0.000 0.001(4) O00B 0.009(4) 0.016(7) 0.023(5) -0.004(5) 0.003(3) 0.002(3) C12A 0.014(8) 0.036(10) 0.025(8) 0.010(7) -0.003(6) 0.009(7) 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' Cl Cl 0.3639 0.7018 '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 C3 O1 C2 114.5(4) . . ? C8 O2 C9 117.8(4) . . ? C13 O4 C12A 126.5(8) . . ? C12 O4 C13 120.4(7) . . ? C15 O5 C14 117.1(5) . . ? C20 O6 C21 117.0(4) . . ? H1A N1 H1B 120.0 . . ? C23 N1 H1A 120.0 . . ? C23 N1 H1B 120.0 . . ? C22 C1 C2 119.9(5) 3_565 . ? C22 C1 C2 120.3(5) . . ? C22 C1 C22 119.8(5) . 3_565 ? O1 C2 C1 107.7(4) . . ? O1 C2 H2A 110.2 . . ? O1 C2 H2B 110.2 . . ? C1 C2 H2A 110.2 . . ? C1 C2 H2B 110.2 . . ? H2A C2 H2B 108.5 . . ? O1 C3 C8 120.1(5) . . ? C4 C3 O1 119.4(5) . . ? C4 C3 C8 120.5(5) . . ? C3 C4 H4 119.7 . . ? C3 C4 C5 120.5(5) . . ? C5 C4 H4 119.7 . . ? C4 C5 H5 120.3 . . ? C6 C5 C4 119.4(6) . . ? C6 C5 H5 120.3 . . ? C5 C6 H6 119.7 . . ? C5 C6 C7 120.7(5) . . ? C7 C6 H6 119.7 . . ? C6 C7 H7 120.2 . . ? C8 C7 C6 119.6(5) . . ? C8 C7 H7 120.2 . . ? O2 C8 C3 116.4(5) . . ? O2 C8 C7 124.4(5) . . ? C7 C8 C3 119.2(5) . . ? O2 C9 H9A 110.3 . . ? O2 C9 H9B 110.3 . . ? O2 C9 C10 107.2(5) . . ? H9A C9 H9B 108.5 . . ? C10 C9 H9A 110.3 . . ? C10 C9 H9B 110.3 . . ? C9 C10 H10A 109.7 . . ? C9 C10 H10B 109.7 . . ? C9 C10 H10C 110.4 . . ? C9 C10 H10D 110.4 . . ? H10A C10 H10B 108.2 . . ? H10C C10 H10D 108.6 . . ? O3A C10 C9 109.9(8) . . ? O3A C10 H10A 109.7 . . ? O3A C10 H10B 109.7 . . ? O00B C10 C9 106.9(5) . . ? O00B C10 H10C 110.4 . . ? O00B C10 H10D 110.4 . . ? H11A C11 H11B 107.2 . . ? H11C C11 H11D 107.1 . . ? O3A C11 H11A 107.9 . . ? O3A C11 H11B 107.9 . . ? O3A C11 C12 117.8(12) . 3_565 ? O3A C11 C12A 112.9(11) . 3_565 ? C12 C11 H11A 107.9 3_565 . ? C12 C11 H11B 107.9 3_565 . ? O00B C11 H11C 107.6 . . ? O00B C11 H11D 107.6 . . ? O00B C11 C12 105.8(9) . 3_565 ? O00B C11 C12A 118.8(9) . 3_565 ? C12A C11 H11C 107.6 3_565 . ? C12A C11 H11D 107.6 3_565 . ? C12A C11 C12 43.7(8) 3_565 3_565 ? O4 C13 C14 110.2(6) . . ? O5 C14 C13 108.2(6) . . ? O5 C14 H14A 110.1 . . ? O5 C14 H14B 110.0 . . ? C13 C14 H14A 110.0 . . ? C13 C14 H14B 110.0 . . ? H14A C14 H14B 108.4 . . ? O5 C15 C20 114.0(5) . . ? C16 C15 O5 125.8(5) . . ? C16 C15 C20 120.2(5) . . ? C15 C16 H16 119.9 . . ? C15 C16 C17 120.2(5) . . ? C17 C16 H16 119.9 . . ? C16 C17 H17 120.0 . . ? C18 C17 C16 120.1(5) . . ? C18 C17 H17 120.0 . . ? C17 C18 H18 119.7 . . ? C17 C18 C19 120.7(6) . . ? C19 C18 H18 119.7 . . ? C18 C19 H19 120.2 . . ? C20 C19 C18 119.7(5) . . ? C20 C19 H19 120.2 . . ? O6 C20 C15 115.2(5) . . ? O6 C20 C19 125.6(5) . . ? C19 C20 C15 119.2(5) . . ? O6 C21 H21A 110.8 . . ? O6 C21 H21B 110.8 . . ? O6 C21 C22 104.6(4) . . ? H21A C21 H21B 108.9 . . ? C22 C21 H21A 110.8 . . ? C22 C21 H21B 110.8 . . ? C1 C22 C1 120.2(5) . 2_665 ? C1 C22 C21 119.3(4) 2_665 . ? C1 C22 C21 120.3(4) . . ? N1 C23 N1 119.74(15) 2_665 3_565 ? N1 C23 N1 119.74(16) 2_665 . ? N1 C23 N1 119.74(15) 3_565 . ? Br2 C24 H24 107.5 . . ? Br3 C24 H24 107.5 . . ? Br3 C24 Br2 109.9(3) . . ? Br4 C24 H24 107.5 . . ? Br4 C24 Br2 112.0(3) . . ? Br4 C24 Br3 112.2(3) . . ? Br2A C24 H24A 105.5 . . ? Br2A C24 Br4A 111.6(4) . . ? Br3A C24 H24A 105.5 . . ? Br3A C24 Br2A 111.2(4) . . ? Br3A C24 Br4A 116.6(4) . . ? Br4A C24 H24A 105.5 . . ? C10 O3A C11 113.6(12) . . ? O4 C12 C11 112.9(8) . 2_665 ? O4 C12 H12A 109.0 . . ? O4 C12 H12B 109.0 . . ? C11 C12 H12A 109.0 2_665 . ? C11 C12 H12B 109.0 2_665 . ? H12A C12 H12B 107.8 . . ? C11 O00B C10 110.3(9) . . ? O4 C12A H12C 109.7 . . ? O4 C12A H12D 109.7 . . ? C11 C12A O4 109.7(11) 2_665 . ? C11 C12A H12C 109.7 2_665 . ? C11 C12A H12D 109.7 2_665 . ? H12C C12A H12D 108.2 . . ? 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 O1 C2 1.439(6) . ? O1 C3 1.389(6) . ? O2 C8 1.368(7) . ? O2 C9 1.433(7) . ? O4 C13 1.407(9) . ? O4 C12 1.301(12) . ? O4 C12A 1.466(16) . ? O5 C14 1.424(7) . ? O5 C15 1.381(7) . ? O6 C20 1.365(6) . ? O6 C21 1.448(6) . ? N1 H1A 0.8800 . ? N1 H1B 0.8800 . ? N1 C23 1.332(9) . ? C1 C2 1.519(7) . ? C1 C22 1.400(7) 3_565 ? C1 C22 1.395(7) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.379(8) . ? C3 C8 1.402(7) . ? C4 H4 0.9500 . ? C4 C5 1.390(8) . ? C5 H5 0.9500 . ? C5 C6 1.389(9) . ? C6 H6 0.9500 . ? C6 C7 1.398(9) . ? C7 H7 0.9500 . ? C7 C8 1.396(7) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C9 C10 1.503(9) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C10 H10C 0.9900 . ? C10 H10D 0.9900 . ? C10 O3A 1.407(16) . ? C10 O00B 1.449(11) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C11 H11C 0.9900 . ? C11 H11D 0.9900 . ? C11 O3A 1.410(17) . ? C11 C12 1.563(13) 3_565 ? C11 O00B 1.423(11) . ? C11 C12A 1.460(18) 3_565 ? C13 C14 1.499(11) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.366(8) . ? C15 C20 1.415(7) . ? C16 H16 0.9500 . ? C16 C17 1.398(9) . ? C17 H17 0.9500 . ? C17 C18 1.367(9) . ? C18 H18 0.9500 . ? C18 C19 1.395(8) . ? C19 H19 0.9500 . ? C19 C20 1.390(7) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C21 C22 1.513(6) . ? C24 H24 1.0000 . ? C24 H24A 1.0000 . ? C24 Br2 1.935(7) . ? C24 Br3 1.926(6) . ? C24 Br4 1.898(6) . ? C24 Br2A 1.903(9) . ? C24 Br3A 1.833(9) . ? C24 Br4A 1.963(8) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C12A H12C 0.9900 . ? C12A H12D 0.9900 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C3 C4 C5 174.4(5) . . . . ? O1 C3 C8 O2 5.1(7) . . . . ? O1 C3 C8 C7 -173.9(5) . . . . ? O2 C9 C10 O3A 55.8(17) . . . . ? O2 C9 C10 O00B 78.9(13) . . . . ? O4 C13 C14 O5 -66.5(8) . . . . ? O5 C15 C16 C17 179.3(5) . . . . ? O5 C15 C20 O6 -1.6(7) . . . . ? O5 C15 C20 C19 -179.9(5) . . . . ? O6 C21 C22 C1 70.6(6) . . . 2_665 ? O6 C21 C22 C1 -104.0(5) . . . . ? C2 O1 C3 C4 107.0(5) . . . . ? C2 O1 C3 C8 -75.9(6) . . . . ? C2 C1 C22 C1 -176.9(3) . . . 2_665 ? C2 C1 C22 C21 -2.3(8) . . . . ? C3 O1 C2 C1 -164.1(4) . . . . ? C3 C4 C5 C6 0.6(8) . . . . ? C4 C3 C8 O2 -177.9(5) . . . . ? C4 C3 C8 C7 3.1(8) . . . . ? C4 C5 C6 C7 0.7(9) . . . . ? C5 C6 C7 C8 -0.2(9) . . . . ? C6 C7 C8 O2 179.4(5) . . . . ? C6 C7 C8 C3 -1.7(9) . . . . ? C8 O2 C9 C10 -155.4(5) . . . . ? C8 C3 C4 C5 -2.6(8) . . . . ? C9 O2 C8 C3 160.6(5) . . . . ? C9 O2 C8 C7 -20.5(8) . . . . ? C9 C10 O3A C11 162.1(19) . . . . ? C9 C10 O00B C11 -171.5(13) . . . . ? C13 O4 C12 C11 -164.3(7) . . . 2_665 ? C13 O4 C12A C11 154.6(8) . . . 2_665 ? C14 O5 C15 C16 9.9(9) . . . . ? C14 O5 C15 C20 -171.0(5) . . . . ? C15 O5 C14 C13 169.6(5) . . . . ? C15 C16 C17 C18 0.0(9) . . . . ? C16 C15 C20 O6 177.6(5) . . . . ? C16 C15 C20 C19 -0.7(8) . . . . ? C16 C17 C18 C19 0.3(9) . . . . ? C17 C18 C19 C20 -0.8(9) . . . . ? C18 C19 C20 O6 -177.2(5) . . . . ? C18 C19 C20 C15 1.0(8) . . . . ? C20 O6 C21 C22 -169.2(4) . . . . ? C20 C15 C16 C17 0.2(8) . . . . ? C21 O6 C20 C15 168.9(4) . . . . ? C21 O6 C20 C19 -12.9(7) . . . . ? C22 C1 C2 O1 100.4(5) 3_565 . . . ? C22 C1 C2 O1 -80.5(6) . . . . ? C22 C1 C22 C1 2.3(10) 3_565 . . 2_665 ? C22 C1 C22 C21 176.9(3) 3_565 . . . ? C12 O4 C13 C14 -144.7(8) . . . . ? C12 C11 O3A C10 -140.0(18) 3_565 . . . ? C12A O4 C13 C14 157.8(11) . . . . ? C12A C11 O00B C10 148.6(13) 3_565 . . . ?