#------------------------------------------------------------------------------ #$Date: 2021-08-13 01:23:18 +0300 (Fri, 13 Aug 2021) $ #$Revision: 268055 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/56/43/1564358.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_1564358 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 '1(Br), 6(C H Cl3), 2(C66 H72 O18), 2(C1 H5.5 N3)' _chemical_formula_sum 'C140 H161 Br Cl18 N6 O36' _chemical_formula_weight 3221.75 _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 _audit_creation_date 2021-03-06 _audit_creation_method ; Olex2 1.3 (compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6257) ; _audit_update_record ; 2021-03-06 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 21.8600(8) _cell_length_b 21.8600(8) _cell_length_c 27.7568(10) _cell_measurement_reflns_used 2295 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 70.8460 _cell_measurement_theta_min 3.9400 _cell_volume 11486.8(7) _computing_cell_refinement 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.46 (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 (Sheldrick, 2015)' _diffrn_ambient_temperature 293(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 8.0697 _diffrn_detector_type EosS2 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.969 _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 -26.00 85.00 1.00 2.00 -- 35.42 0.00 -30.00 111 2 \w 38.00 109.00 1.00 4.00 -- 105.82 -94.00-150.00 71 3 \w 43.00 121.00 1.00 4.00 -- 105.82 -45.00-180.00 78 4 \w 82.00 108.00 1.00 4.00 -- 105.82 15.00 -90.00 26 5 \w 124.00 172.00 1.00 4.00 -- 105.82 15.00 -90.00 48 6 \w 81.00 126.00 1.00 4.00 -- 105.82 77.00 -60.00 45 7 \w 24.00 61.00 1.00 2.00 -- 35.42-125.00 -60.00 37 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, EosS2' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0562700000 _diffrn_orient_matrix_UB_12 0.0214759000 _diffrn_orient_matrix_UB_13 -0.0091913000 _diffrn_orient_matrix_UB_21 -0.0281629000 _diffrn_orient_matrix_UB_22 -0.0225851000 _diffrn_orient_matrix_UB_23 0.0516497000 _diffrn_orient_matrix_UB_31 0.0516170000 _diffrn_orient_matrix_UB_32 0.0751032000 _diffrn_orient_matrix_UB_33 0.0181392000 _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 0.0278 _diffrn_reflns_av_unetI/netI 0.0465 _diffrn_reflns_Laue_measured_fraction_full 0.996 _diffrn_reflns_Laue_measured_fraction_max 0.969 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_number 8089 _diffrn_reflns_point_group_measured_fraction_full 0.996 _diffrn_reflns_point_group_measured_fraction_max 0.969 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 72.328 _diffrn_reflns_theta_min 2.825 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 3.886 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.46917 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.397 _exptl_crystal_description cubic _exptl_crystal_F_000 5016 _exptl_crystal_size_max 0.125 _exptl_crystal_size_mid 0.114 _exptl_crystal_size_min 0.086 _refine_diff_density_max 0.520 _refine_diff_density_min -0.805 _refine_diff_density_rms 0.082 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 313 _refine_ls_number_reflns 4902 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.068 _refine_ls_R_factor_all 0.1225 _refine_ls_R_factor_gt 0.1013 _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^)+(0.1594P)^2^+43.9422P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2969 _refine_ls_wR_factor_ref 0.3200 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3566 _reflns_number_total 4902 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1sc03713g2.cif _cod_data_source_block 1-GuaBr _cod_original_cell_volume 11486.8(9) _cod_original_sg_symbol_H-M 'R -3' _cod_database_code 1564358 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula 'C30 O10 H50' _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. ; _reflns_odcompleteness_completeness 99.65 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.49 _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 O6-C22 \\sim O6-C22A with sigma of 0.02 3. Others Sof(H1BC)=Sof(H1BD)=Sof(C22A)=Sof(H22C)=Sof(H22D)=1-FVAR(1) Sof(H1AA)=Sof(H1AB)=Sof(C22)=Sof(H22A)=Sof(H22B)=FVAR(1) Fixed Sof: H1A(0.91667) H1B(0.91667) 4.a Ternary CH refined with riding coordinates: C24(H24) 4.b Secondary CH2 refined with riding coordinates: C1(H1AA,H1AB), C1(H1BC,H1BD), C2(H2A,H2B), C3(H3A,H3B), C10(H10A,H10B), C13(H13A,H13B), C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B), C22A(H22C,H22D) 4.c Aromatic/amide H refined with riding coordinates: C5(H5), C6(H6), C7(H7), C8(H8), C15(H15), C16(H16), C17(H17), C18(H18) 4.d X=CH2 refined with riding coordinates: N1(H1A,H1B) ; _shelx_res_file ; TITL exp_1294_a.res in R-3 exp_1294.res created by SHELXL-2018/3 at 15:24:34 on 06-Mar-2021 REM Old TITL exp_1294 in R-3 REM SHELXT solution in R-3 REM R1 0.294, Rweak 0.047, Alpha 0.052, Orientation as input REM Formula found by SHELXT: C152 O42 Cl CELL 1.54184 21.86 21.86 27.7568 90 90 120 ZERR 3 0.0008 0.0008 0.001 0 0 0 LATT 3 SYMM -Y,+X-Y,+Z SYMM +Y-X,-X,+Z SFAC C H Br Cl N O UNIT 420 483 3 54 18 108 SADI O6 C22 O6 C22A L.S. 10 0 0 PLAN 5 CONF BOND list 4 MORE -1 BOND $H fmap 2 53 acta REM REM REM WGHT 0.159400 43.942200 FVAR 0.14288 0.60398 BR1 3 0.666667 0.333333 0.333333 10.16667 0.13475 0.13475 = 0.08315 0.00000 0.00000 0.06737 CL1 4 0.538788 0.396128 0.424279 11.00000 0.08722 0.24773 = 0.22835 0.12928 0.02484 0.05148 CL2 4 0.652759 0.521503 0.388556 11.00000 0.12523 0.13038 = 0.20714 0.04036 -0.02357 0.01404 CL3 4 0.673075 0.448875 0.465562 11.00000 0.20525 0.26010 = 0.17168 -0.03834 -0.09899 0.12950 O1 6 0.883259 0.712247 0.320565 11.00000 0.06416 0.12584 = 0.10964 0.02682 0.00046 0.03817 O2 6 0.897636 0.705971 0.422564 11.00000 0.06161 0.04585 = 0.08439 -0.01278 -0.00527 0.02516 O3 6 0.981780 0.834350 0.462664 11.00000 0.06722 0.04402 = 0.04522 0.00200 0.00655 0.03517 O4 6 0.842000 0.867858 0.365961 11.00000 0.03779 0.04810 = 0.04374 0.00190 -0.00557 0.01076 O5 6 0.797463 0.882606 0.283935 11.00000 0.05846 0.07340 = 0.05141 0.00930 -0.00533 0.02724 O6 6 0.836547 1.021630 0.257343 11.00000 0.07250 0.06461 = 0.10430 -0.00810 0.00261 0.02444 N1 5 0.955426 0.932715 0.290519 11.00000 0.10813 0.09035 = 0.15267 0.00115 0.03190 0.04479 AFIX 93 H1A 2 0.970509 0.903304 0.287831 10.91667 -1.20000 H1B 2 0.910792 0.917518 0.291859 10.91667 -1.20000 AFIX 0 C1 1 0.860517 0.737932 0.284535 11.00000 0.06000 0.09068 = 0.11742 0.00321 -0.00516 0.03788 PART 1 AFIX 23 H1AA 2 0.853384 0.775322 0.297073 21.00000 -1.20000 H1AB 2 0.815495 0.700597 0.272617 21.00000 -1.20000 AFIX 23 PART 2 H1BC 2 0.820510 0.741311 0.296264 -21.00000 -1.20000 H1BD 2 0.843794 0.704121 0.258278 -21.00000 -1.20000 AFIX 0 PART 0 C2 1 0.830419 0.664802 0.351594 11.00000 0.05500 0.06016 = 0.09518 -0.02072 0.00057 0.01715 AFIX 23 H2A 2 0.797648 0.622476 0.334149 11.00000 -1.20000 H2B 2 0.804349 0.686097 0.364789 11.00000 -1.20000 AFIX 0 C3 1 0.864225 0.646679 0.390889 11.00000 0.06350 0.04599 = 0.09929 -0.01527 -0.00053 0.02036 AFIX 23 H3A 2 0.829026 0.605555 0.408257 11.00000 -1.20000 H3B 2 0.898917 0.635941 0.377766 11.00000 -1.20000 AFIX 0 C4 1 0.951748 0.712955 0.450451 11.00000 0.05933 0.04149 = 0.06916 0.00546 0.01074 0.02784 C5 1 0.965713 0.659037 0.462043 11.00000 0.08922 0.04488 = 0.09364 0.00865 0.01249 0.03636 AFIX 43 H5 2 0.936052 0.613492 0.450720 11.00000 -1.20000 AFIX 0 C6 1 1.023438 0.672868 0.490296 11.00000 0.11845 0.08234 = 0.07401 0.02389 0.01396 0.07469 AFIX 43 H6 2 1.031906 0.636371 0.498056 11.00000 -1.20000 AFIX 0 C7 1 1.067622 0.738828 0.506725 11.00000 0.10183 0.09156 = 0.05059 0.00953 0.00503 0.07241 AFIX 43 H7 2 1.106785 0.747662 0.525096 11.00000 -1.20000 AFIX 0 C8 1 1.054652 0.793393 0.496228 11.00000 0.07239 0.06713 = 0.04076 0.00042 0.00391 0.04354 AFIX 43 H8 2 1.085030 0.838664 0.507720 11.00000 -1.20000 AFIX 0 C9 1 0.996876 0.780685 0.468818 11.00000 0.06388 0.04790 = 0.04265 0.00614 0.01059 0.03498 C10 1 0.995668 0.864822 0.415290 11.00000 0.05695 0.04118 = 0.04215 -0.00150 0.00000 0.02757 AFIX 23 H10A 2 0.958781 0.833509 0.393254 11.00000 -1.20000 H10B 2 1.040430 0.871590 0.403544 11.00000 -1.20000 AFIX 0 C11 1 0.998041 0.934998 0.417939 11.00000 0.04451 0.03610 = 0.03614 -0.00270 -0.00207 0.02182 C12 1 0.935279 0.937228 0.418258 11.00000 0.03420 0.03766 = 0.03734 0.00055 -0.00339 0.01341 C13 1 0.865048 0.869825 0.414900 11.00000 0.03948 0.04133 = 0.04584 0.00493 -0.00466 0.01176 AFIX 23 H13A 2 0.870285 0.829146 0.421661 11.00000 -1.20000 H13B 2 0.831490 0.870381 0.437505 11.00000 -1.20000 AFIX 0 C14 1 0.774262 0.816616 0.354544 11.00000 0.03776 0.04028 = 0.05196 -0.00827 -0.00622 0.01604 C15 1 0.731851 0.759930 0.383639 11.00000 0.04496 0.04607 = 0.06032 0.00129 -0.00697 0.01392 AFIX 43 H15 2 0.747592 0.755209 0.413789 11.00000 -1.20000 AFIX 0 C16 1 0.664727 0.709552 0.367156 11.00000 0.04659 0.04634 = 0.08131 0.00108 -0.00819 0.00689 AFIX 43 H16 2 0.635995 0.670521 0.386162 11.00000 -1.20000 AFIX 0 C17 1 0.641189 0.717482 0.323185 11.00000 0.04665 0.05654 = 0.07690 -0.01608 -0.01592 0.01351 AFIX 43 H17 2 0.596341 0.684092 0.312584 11.00000 -1.20000 AFIX 0 C18 1 0.683506 0.774494 0.294706 11.00000 0.05527 0.06798 = 0.05831 -0.01138 -0.01675 0.02906 AFIX 43 H18 2 0.666940 0.779695 0.265004 11.00000 -1.20000 AFIX 0 C19 1 0.750466 0.824249 0.309699 11.00000 0.04573 0.05232 = 0.04689 -0.00595 -0.00364 0.02417 C20 1 0.772160 0.898159 0.240890 11.00000 0.09004 0.07338 = 0.04708 -0.00261 -0.01326 0.03781 AFIX 23 H20A 2 0.727925 0.896965 0.247175 11.00000 -1.20000 H20B 2 0.763996 0.863333 0.216314 11.00000 -1.20000 AFIX 0 C21 1 0.826203 0.969582 0.224167 11.00000 0.11538 0.09154 = 0.05928 0.01050 0.00015 0.05159 AFIX 23 H21A 2 0.870528 0.970495 0.218945 11.00000 -1.20000 H21B 2 0.811364 0.979564 0.193655 11.00000 -1.20000 AFIX 0 PART 1 C22 1 0.853061 1.086020 0.242636 21.00000 0.09170 0.07282 = 0.07679 0.02173 0.01153 0.04285 AFIX 23 H22A 2 0.812184 1.083902 0.227281 21.00000 -1.20000 H22B 2 0.890480 1.102212 0.218845 21.00000 -1.20000 AFIX 0 PART 0 C23 1 1.000000 1.000000 0.292552 10.33333 0.08160 0.08160 = 0.07989 0.00000 0.00000 0.04080 C24 1 0.627315 0.439190 0.414376 11.00000 0.08160 0.11085 = 0.09140 0.00003 -0.00749 0.03954 AFIX 13 H24 2 0.637811 0.411551 0.391475 11.00000 -1.20000 AFIX 0 PART 2 C22A 1 0.894352 1.085796 0.264929 -21.00000 0.09034 0.16808 = 0.09637 -0.00260 0.00346 0.05809 AFIX 23 H22C 2 0.919561 1.103094 0.234730 -21.00000 -1.20000 H22D 2 0.925491 1.080531 0.287311 -21.00000 -1.20000 AFIX 0 HKLF 4 REM exp_1294_a.res in R-3 REM wR2 = 0.3200, GooF = S = 1.068, Restrained GooF = 1.068 for all data REM R1 = 0.1013 for 3566 Fo > 4sig(Fo) and 0.1225 for all 4902 data REM 313 parameters refined using 1 restraints END WGHT 0.1597 43.7405 REM Highest difference peak 0.520, deepest hole -0.805, 1-sigma level 0.082 Q1 1 0.5694 0.4564 0.4431 11.00000 0.05 0.52 Q2 1 0.6621 0.5106 0.4343 11.00000 0.05 0.42 Q3 1 0.6553 0.4786 0.3550 11.00000 0.05 0.41 Q4 1 0.6178 0.4987 0.4350 11.00000 0.05 0.31 Q5 1 0.6871 0.5109 0.4204 11.00000 0.05 0.31 ; _shelx_res_checksum 95218 _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 1.796 _oxdiff_exptl_absorpt_empirical_full_min 0.705 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 Br1 Br 0.666667 0.333333 0.333333 0.1175(8) Uani 1 6 d S T P . . Cl1 Cl 0.53879(15) 0.3961(2) 0.42428(16) 0.202(2) Uani 1 1 d . . . . . Cl2 Cl 0.65276(17) 0.52150(18) 0.38856(15) 0.1764(16) Uani 1 1 d . . . . . Cl3 Cl 0.6731(2) 0.4489(3) 0.46556(15) 0.206(2) Uani 1 1 d . . . . . O1 O 0.8833(2) 0.7122(3) 0.3206(2) 0.1040(17) Uani 1 1 d . . . . . O2 O 0.89764(19) 0.70597(17) 0.42256(14) 0.0647(9) Uani 1 1 d . . . . . O3 O 0.98178(17) 0.83435(15) 0.46266(10) 0.0489(7) Uani 1 1 d . . . . . O4 O 0.84200(15) 0.86786(15) 0.36596(10) 0.0480(7) Uani 1 1 d . . . . . O5 O 0.79746(18) 0.8826(2) 0.28393(12) 0.0636(9) Uani 1 1 d . . . . . O6 O 0.8365(2) 1.0216(2) 0.25734(18) 0.0848(12) Uani 1 1 d D . . . . N1 N 0.9554(4) 0.9327(4) 0.2905(3) 0.119(2) Uani 1 1 d . . . . . H1A H 0.970509 0.903304 0.287831 0.143 Uiso 0.9167 1 calc R U P . . H1B H 0.910792 0.917518 0.291859 0.143 Uiso 0.9167 1 calc R U P . . C1 C 0.8605(3) 0.7379(4) 0.2845(3) 0.0893(19) Uani 1 1 d . . . . . H1AA H 0.853384 0.775322 0.297073 0.107 Uiso 0.60(2) 1 calc R U P A 1 H1AB H 0.815495 0.700597 0.272617 0.107 Uiso 0.60(2) 1 calc R U P A 1 H1BC H 0.820510 0.741311 0.296264 0.107 Uiso 0.40(2) 1 calc R U P A 2 H1BD H 0.843794 0.704121 0.258278 0.107 Uiso 0.40(2) 1 calc R U P A 2 C2 C 0.8304(3) 0.6648(3) 0.3516(2) 0.0753(16) Uani 1 1 d . . . . . H2A H 0.797648 0.622476 0.334149 0.090 Uiso 1 1 calc R U . . . H2B H 0.804349 0.686097 0.364789 0.090 Uiso 1 1 calc R U . . . C3 C 0.8642(3) 0.6467(3) 0.3909(2) 0.0727(15) Uani 1 1 d . . . . . H3A H 0.829026 0.605555 0.408257 0.087 Uiso 1 1 calc R U . . . H3B H 0.898917 0.635941 0.377766 0.087 Uiso 1 1 calc R U . . . C4 C 0.9517(3) 0.7130(2) 0.45045(18) 0.0555(11) Uani 1 1 d . . . . . C5 C 0.9657(4) 0.6590(3) 0.4620(2) 0.0747(16) Uani 1 1 d . . . . . H5 H 0.936052 0.613492 0.450720 0.090 Uiso 1 1 calc R U . . . C6 C 1.0234(4) 0.6729(4) 0.4903(2) 0.0807(18) Uani 1 1 d . . . . . H6 H 1.031906 0.636371 0.498056 0.097 Uiso 1 1 calc R U . . . C7 C 1.0676(4) 0.7388(3) 0.50672(18) 0.0706(15) Uani 1 1 d . . . . . H7 H 1.106785 0.747662 0.525096 0.085 Uiso 1 1 calc R U . . . C8 C 1.0547(3) 0.7934(3) 0.49623(16) 0.0562(11) Uani 1 1 d . . . . . H8 H 1.085030 0.838664 0.507720 0.067 Uiso 1 1 calc R U . . . C9 C 0.9969(3) 0.7807(2) 0.46882(15) 0.0484(10) Uani 1 1 d . . . . . C10 C 0.9957(2) 0.8648(2) 0.41529(14) 0.0454(9) Uani 1 1 d . . . . . H10A H 0.958781 0.833509 0.393254 0.054 Uiso 1 1 calc R U . . . H10B H 1.040430 0.871590 0.403544 0.054 Uiso 1 1 calc R U . . . C11 C 0.9980(2) 0.93500(19) 0.41794(13) 0.0382(8) Uani 1 1 d . . . . . C12 C 0.93528(19) 0.93723(19) 0.41826(13) 0.0384(8) Uani 1 1 d . . . . . C13 C 0.8650(2) 0.8698(2) 0.41490(15) 0.0460(9) Uani 1 1 d . . . . . H13A H 0.870285 0.829146 0.421661 0.055 Uiso 1 1 calc R U . . . H13B H 0.831490 0.870381 0.437505 0.055 Uiso 1 1 calc R U . . . C14 C 0.7743(2) 0.8166(2) 0.35454(16) 0.0449(9) Uani 1 1 d . . . . . C15 C 0.7319(2) 0.7599(2) 0.38364(18) 0.0544(11) Uani 1 1 d . . . . . H15 H 0.747592 0.755209 0.413789 0.065 Uiso 1 1 calc R U . . . C16 C 0.6647(3) 0.7096(3) 0.3672(2) 0.0653(13) Uani 1 1 d . . . . . H16 H 0.635995 0.670521 0.386162 0.078 Uiso 1 1 calc R U . . . C17 C 0.6412(3) 0.7175(3) 0.3232(2) 0.0655(13) Uani 1 1 d . . . . . H17 H 0.596341 0.684092 0.312584 0.079 Uiso 1 1 calc R U . . . C18 C 0.6835(3) 0.7745(3) 0.29471(19) 0.0613(12) Uani 1 1 d . . . . . H18 H 0.666940 0.779695 0.265004 0.074 Uiso 1 1 calc R U . . . C19 C 0.7505(2) 0.8242(2) 0.30970(16) 0.0485(9) Uani 1 1 d . . . . . C20 C 0.7722(3) 0.8982(3) 0.24089(19) 0.0715(15) Uani 1 1 d . . . . . H20A H 0.727925 0.896965 0.247175 0.086 Uiso 1 1 calc R U . . . H20B H 0.763996 0.863333 0.216314 0.086 Uiso 1 1 calc R U . . . C21 C 0.8262(5) 0.9696(4) 0.2242(2) 0.0888(19) Uani 1 1 d . . . . . H21A H 0.870528 0.970495 0.218945 0.107 Uiso 1 1 calc R U . . . H21B H 0.811364 0.979564 0.193655 0.107 Uiso 1 1 calc R U . . . C22 C 0.8531(8) 1.0860(6) 0.2426(4) 0.080(4) Uani 0.60(2) 1 d D . P A 1 H22A H 0.812184 1.083902 0.227281 0.096 Uiso 0.60(2) 1 calc R U P A 1 H22B H 0.890480 1.102212 0.218845 0.096 Uiso 0.60(2) 1 calc R U P A 1 C23 C 1.000000 1.000000 0.2926(4) 0.081(3) Uani 1 3 d S T P . . C24 C 0.6273(4) 0.4392(5) 0.4144(3) 0.098(2) Uani 1 1 d . . . . . H24 H 0.637811 0.411551 0.391475 0.118 Uiso 1 1 calc R U . . . C22A C 0.8944(11) 1.0858(12) 0.2649(9) 0.121(10) Uani 0.40(2) 1 d D . P A 2 H22C H 0.919561 1.103094 0.234730 0.145 Uiso 0.40(2) 1 calc R U P A 2 H22D H 0.925491 1.080531 0.287311 0.145 Uiso 0.40(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 Br1 0.1347(12) 0.1347(12) 0.0832(13) 0.000 0.000 0.0674(6) Cl1 0.0872(16) 0.248(4) 0.228(4) 0.129(3) 0.0248(19) 0.051(2) Cl2 0.125(2) 0.130(2) 0.207(4) 0.040(2) -0.024(2) 0.0140(17) Cl3 0.205(4) 0.260(5) 0.172(3) -0.038(3) -0.099(3) 0.129(4) O1 0.064(3) 0.126(4) 0.110(4) 0.027(3) 0.000(2) 0.038(3) O2 0.062(2) 0.0458(17) 0.084(2) -0.0128(16) -0.0053(17) 0.0252(16) O3 0.0672(19) 0.0440(15) 0.0452(15) 0.0020(12) 0.0066(13) 0.0352(14) O4 0.0378(14) 0.0481(16) 0.0437(15) 0.0019(12) -0.0056(11) 0.0108(12) O5 0.0585(19) 0.073(2) 0.0514(18) 0.0093(15) -0.0053(14) 0.0272(17) O6 0.073(3) 0.065(2) 0.104(3) -0.008(2) 0.003(2) 0.024(2) N1 0.108(5) 0.090(4) 0.153(7) 0.001(4) 0.032(5) 0.045(4) C1 0.060(3) 0.091(5) 0.117(6) 0.003(4) -0.005(3) 0.038(3) C2 0.055(3) 0.060(3) 0.095(4) -0.021(3) 0.001(3) 0.017(2) C3 0.063(3) 0.046(3) 0.099(4) -0.015(3) -0.001(3) 0.020(2) C4 0.059(3) 0.041(2) 0.069(3) 0.0055(19) 0.011(2) 0.028(2) C5 0.089(4) 0.045(3) 0.094(4) 0.009(3) 0.012(3) 0.036(3) C6 0.118(5) 0.082(4) 0.074(4) 0.024(3) 0.014(3) 0.075(4) C7 0.102(4) 0.092(4) 0.051(3) 0.010(3) 0.005(3) 0.072(4) C8 0.072(3) 0.067(3) 0.041(2) 0.0004(19) 0.004(2) 0.044(3) C9 0.064(3) 0.048(2) 0.043(2) 0.0061(17) 0.0106(18) 0.035(2) C10 0.057(2) 0.041(2) 0.042(2) -0.0015(16) 0.0000(17) 0.0276(19) C11 0.045(2) 0.0361(18) 0.0361(18) -0.0027(14) -0.0021(15) 0.0218(16) C12 0.0342(18) 0.0377(18) 0.0373(18) 0.0005(14) -0.0034(14) 0.0134(15) C13 0.039(2) 0.041(2) 0.046(2) 0.0049(16) -0.0047(16) 0.0118(17) C14 0.0378(19) 0.040(2) 0.052(2) -0.0083(16) -0.0062(16) 0.0160(16) C15 0.045(2) 0.046(2) 0.060(3) 0.0013(19) -0.0070(19) 0.0139(19) C16 0.047(2) 0.046(2) 0.081(3) 0.001(2) -0.008(2) 0.007(2) C17 0.047(2) 0.057(3) 0.077(3) -0.016(2) -0.016(2) 0.014(2) C18 0.055(3) 0.068(3) 0.058(3) -0.011(2) -0.017(2) 0.029(2) C19 0.046(2) 0.052(2) 0.047(2) -0.0059(18) -0.0036(17) 0.0242(19) C20 0.090(4) 0.073(3) 0.047(3) -0.003(2) -0.013(2) 0.038(3) C21 0.115(6) 0.092(5) 0.059(3) 0.011(3) 0.000(3) 0.052(4) C22 0.092(9) 0.073(7) 0.077(7) 0.022(5) 0.012(6) 0.043(6) C23 0.082(4) 0.082(4) 0.080(7) 0.000 0.000 0.041(2) C24 0.082(4) 0.111(6) 0.091(5) 0.000(4) -0.007(4) 0.040(4) C22A 0.090(15) 0.17(3) 0.096(16) -0.003(15) 0.003(12) 0.058(16) 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 C1 O1 C2 115.0(5) . . ? C4 O2 C3 118.3(4) . . ? C9 O3 C10 115.0(3) . . ? C14 O4 C13 117.4(3) . . ? C19 O5 C20 117.3(4) . . ? C22 O6 C21 120.6(7) . . ? C22A O6 C21 129.5(11) . . ? H1A N1 H1B 120.0 . . ? C23 N1 H1A 120.0 . . ? C23 N1 H1B 120.0 . . ? O1 C1 H1AA 109.3 . . ? O1 C1 H1AB 109.3 . . ? O1 C1 H1BC 108.4 . . ? O1 C1 H1BD 108.4 . . ? O1 C1 C22 111.6(6) . 2_765 ? O1 C1 C22A 115.7(10) . 2_765 ? H1AA C1 H1AB 108.0 . . ? H1BC C1 H1BD 107.4 . . ? C22 C1 H1AA 109.3 2_765 . ? C22 C1 H1AB 109.3 2_765 . ? C22A C1 H1BC 108.4 2_765 . ? C22A C1 H1BD 108.4 2_765 . ? O1 C2 H2A 110.0 . . ? O1 C2 H2B 110.0 . . ? O1 C2 C3 108.4(5) . . ? H2A C2 H2B 108.4 . . ? C3 C2 H2A 110.0 . . ? C3 C2 H2B 110.0 . . ? O2 C3 C2 108.0(5) . . ? O2 C3 H3A 110.1 . . ? O2 C3 H3B 110.1 . . ? C2 C3 H3A 110.1 . . ? C2 C3 H3B 110.1 . . ? H3A C3 H3B 108.4 . . ? O2 C4 C5 125.7(5) . . ? O2 C4 C9 116.1(4) . . ? C5 C4 C9 118.2(5) . . ? C4 C5 H5 119.8 . . ? C6 C5 C4 120.4(6) . . ? C6 C5 H5 119.8 . . ? C5 C6 H6 119.6 . . ? C7 C6 C5 120.7(5) . . ? C7 C6 H6 119.6 . . ? C6 C7 H7 119.9 . . ? C6 C7 C8 120.1(6) . . ? C8 C7 H7 119.9 . . ? C7 C8 H8 119.9 . . ? C9 C8 C7 120.2(5) . . ? C9 C8 H8 119.9 . . ? O3 C9 C4 120.8(4) . . ? C8 C9 O3 118.8(4) . . ? C8 C9 C4 120.2(4) . . ? O3 C10 H10A 110.0 . . ? O3 C10 H10B 110.0 . . ? O3 C10 C11 108.6(3) . . ? H10A C10 H10B 108.4 . . ? C11 C10 H10A 110.0 . . ? C11 C10 H10B 110.0 . . ? C12 C11 C10 120.4(3) 2_765 . ? C12 C11 C10 120.0(3) . . ? C12 C11 C12 119.6(4) 2_765 . ? C11 C12 C11 120.4(4) . 3_675 ? C11 C12 C13 120.2(4) . . ? C11 C12 C13 119.2(3) 3_675 . ? O4 C13 C12 104.9(3) . . ? O4 C13 H13A 110.8 . . ? O4 C13 H13B 110.8 . . ? C12 C13 H13A 110.8 . . ? C12 C13 H13B 110.8 . . ? H13A C13 H13B 108.8 . . ? O4 C14 C15 124.3(4) . . ? O4 C14 C19 115.1(4) . . ? C15 C14 C19 120.6(4) . . ? C14 C15 H15 120.5 . . ? C14 C15 C16 119.0(4) . . ? C16 C15 H15 120.5 . . ? C15 C16 H16 119.9 . . ? C17 C16 C15 120.3(5) . . ? C17 C16 H16 119.9 . . ? C16 C17 H17 119.9 . . ? C16 C17 C18 120.2(4) . . ? C18 C17 H17 119.9 . . ? C17 C18 H18 119.7 . . ? C17 C18 C19 120.6(5) . . ? C19 C18 H18 119.7 . . ? O5 C19 C14 115.3(4) . . ? O5 C19 C18 125.5(4) . . ? C18 C19 C14 119.2(4) . . ? O5 C20 H20A 110.1 . . ? O5 C20 H20B 110.1 . . ? O5 C20 C21 108.2(5) . . ? H20A C20 H20B 108.4 . . ? C21 C20 H20A 110.1 . . ? C21 C20 H20B 110.1 . . ? O6 C21 C20 111.8(5) . . ? O6 C21 H21A 109.3 . . ? O6 C21 H21B 109.3 . . ? C20 C21 H21A 109.3 . . ? C20 C21 H21B 109.3 . . ? H21A C21 H21B 107.9 . . ? O6 C22 C1 112.2(9) . 3_675 ? O6 C22 H22A 109.2 . . ? O6 C22 H22B 109.2 . . ? C1 C22 H22A 109.2 3_675 . ? C1 C22 H22B 109.2 3_675 . ? H22A C22 H22B 107.9 . . ? N1 C23 N1 119.81(10) . 3_675 ? N1 C23 N1 119.81(11) 2_765 3_675 ? N1 C23 N1 119.81(10) . 2_765 ? Cl1 C24 Cl2 108.9(5) . . ? Cl1 C24 H24 108.4 . . ? Cl2 C24 H24 108.4 . . ? Cl3 C24 Cl1 111.9(5) . . ? Cl3 C24 Cl2 110.6(5) . . ? Cl3 C24 H24 108.4 . . ? O6 C22A C1 113.5(17) . 3_675 ? O6 C22A H22C 108.9 . . ? O6 C22A H22D 108.9 . . ? C1 C22A H22C 108.9 3_675 . ? C1 C22A H22D 108.9 3_675 . ? H22C C22A H22D 107.7 . . ? 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 Cl1 C24 1.699(8) . ? Cl2 C24 1.749(9) . ? Cl3 C24 1.689(8) . ? O1 C1 1.357(9) . ? O1 C2 1.398(8) . ? O2 C3 1.428(6) . ? O2 C4 1.357(6) . ? O3 C9 1.379(5) . ? O3 C10 1.436(5) . ? O4 C13 1.442(5) . ? O4 C14 1.374(5) . ? O5 C19 1.372(6) . ? O5 C20 1.427(6) . ? O6 C21 1.392(8) . ? O6 C22 1.330(10) . ? O6 C22A 1.355(17) . ? N1 H1A 0.8600 . ? N1 H1B 0.8600 . ? N1 C23 1.297(7) . ? C1 H1AA 0.9700 . ? C1 H1AB 0.9700 . ? C1 H1BC 0.9700 . ? C1 H1BD 0.9700 . ? C1 C22 1.543(15) 2_765 ? C1 C22A 1.50(3) 2_765 ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C2 C3 1.478(9) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.395(7) . ? C4 C9 1.402(7) . ? C5 H5 0.9300 . ? C5 C6 1.385(10) . ? C6 H6 0.9300 . ? C6 C7 1.352(10) . ? C7 H7 0.9300 . ? C7 C8 1.388(7) . ? C8 H8 0.9300 . ? C8 C9 1.379(7) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C10 C11 1.511(5) . ? C11 C12 1.397(5) 2_765 ? C11 C12 1.397(5) . ? C12 C13 1.508(5) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.378(6) . ? C14 C19 1.391(6) . ? C15 H15 0.9300 . ? C15 C16 1.400(6) . ? C16 H16 0.9300 . ? C16 C17 1.369(8) . ? C17 H17 0.9300 . ? C17 C18 1.371(8) . ? C18 H18 0.9300 . ? C18 C19 1.381(7) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C20 C21 1.485(9) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C24 H24 0.9800 . ? C22A H22C 0.9700 . ? C22A H22D 0.9700 . ? 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 C2 C3 O2 74.0(6) . . . . ? O2 C4 C5 C6 178.9(5) . . . . ? O2 C4 C9 O3 6.6(6) . . . . ? O2 C4 C9 C8 -177.9(4) . . . . ? O3 C10 C11 C12 -80.7(4) . . . . ? O3 C10 C11 C12 101.7(4) . . . 2_765 ? O4 C14 C15 C16 -177.4(5) . . . . ? O4 C14 C19 O5 -1.4(6) . . . . ? O4 C14 C19 C18 178.8(4) . . . . ? O5 C20 C21 O6 -63.1(8) . . . . ? C1 O1 C2 C3 -175.2(6) . . . . ? C2 O1 C1 C22 -159.6(7) . . . 2_765 ? C2 O1 C1 C22A 154.3(13) . . . 2_765 ? C3 O2 C4 C5 -19.7(8) . . . . ? C3 O2 C4 C9 160.3(5) . . . . ? C4 O2 C3 C2 -156.7(5) . . . . ? C4 C5 C6 C7 -0.7(10) . . . . ? C5 C4 C9 O3 -173.4(4) . . . . ? C5 C4 C9 C8 2.1(7) . . . . ? C5 C6 C7 C8 1.4(9) . . . . ? C6 C7 C8 C9 -0.3(8) . . . . ? C7 C8 C9 O3 174.2(4) . . . . ? C7 C8 C9 C4 -1.5(7) . . . . ? C9 O3 C10 C11 -163.1(4) . . . . ? C9 C4 C5 C6 -1.1(8) . . . . ? C10 O3 C9 C4 -76.2(5) . . . . ? C10 O3 C9 C8 108.2(4) . . . . ? C10 C11 C12 C11 -176.4(3) . . . 3_675 ? C10 C11 C12 C13 -1.3(5) . . . . ? C11 C12 C13 O4 -103.7(4) . . . . ? C11 C12 C13 O4 71.4(5) 3_675 . . . ? C12 C11 C12 C11 1.3(7) 2_765 . . 3_675 ? C12 C11 C12 C13 176.3(3) 2_765 . . . ? C13 O4 C14 C15 -12.3(6) . . . . ? C13 O4 C14 C19 169.4(4) . . . . ? C14 O4 C13 C12 -171.1(3) . . . . ? C14 C15 C16 C17 -1.4(8) . . . . ? C15 C14 C19 O5 -179.8(4) . . . . ? C15 C14 C19 C18 0.4(7) . . . . ? C15 C16 C17 C18 0.7(9) . . . . ? C16 C17 C18 C19 0.6(9) . . . . ? C17 C18 C19 O5 179.1(5) . . . . ? C17 C18 C19 C14 -1.1(8) . . . . ? C19 O5 C20 C21 169.2(5) . . . . ? C19 C14 C15 C16 0.8(7) . . . . ? C20 O5 C19 C14 -171.5(4) . . . . ? C20 O5 C19 C18 8.4(7) . . . . ? C21 O6 C22 C1 -167.9(7) . . . 3_675 ? C21 O6 C22A C1 151.8(11) . . . 3_675 ? C22 O6 C21 C20 -147.2(9) . . . . ? C22A O6 C21 C20 153.9(19) . . . . ?