#------------------------------------------------------------------------------ #$Date: 2021-08-13 01:23:18 +0300 (Fri, 13 Aug 2021) $ #$Revision: 268055 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/56/43/1564359.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_1564359 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(Cl), 6(C H0.969 Cl3), 2(C66 H70.574 O18), 2(C1 H5.5 N3)' _chemical_formula_sum 'C140 H157.96 Cl19 N6 O36' _chemical_formula_weight 3174.22 _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 mixed _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 21.694(3) _cell_length_b 21.694(3) _cell_length_c 27.480(4) _cell_measurement_reflns_used 1594 _cell_measurement_temperature 150.15 _cell_measurement_theta_max 22.15 _cell_measurement_theta_min 2.29 _cell_volume 11200(3) _computing_cell_refinement 'SAINT V8.38A (Bruker, 2018)' _computing_data_reduction 'SAINT V8.38A (Bruker, 2018)' _computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 150.15 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0351 _diffrn_reflns_av_unetI/netI 0.0287 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_number 24200 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 30.058 _diffrn_reflns_theta_min 2.291 _diffrn_source_current 1.4 _diffrn_source_power 0.07 _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.425 _exptl_absorpt_correction_T_max 0.7460 _exptl_absorpt_correction_T_min 0.6000 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1367 before and 0.0540 after correction. The Ratio of minimum to maximum transmission is 0.8043. The \l/2 correction factor is Not present. ; _exptl_crystal_density_diffrn 1.412 _exptl_crystal_description bulk _exptl_crystal_F_000 4953 _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.359 _exptl_crystal_size_min 0.311 _refine_diff_density_max 0.526 _refine_diff_density_min -0.990 _refine_diff_density_rms 0.105 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.155 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 361 _refine_ls_number_reflns 7306 _refine_ls_number_restraints 24 _refine_ls_restrained_S_all 1.157 _refine_ls_R_factor_all 0.1128 _refine_ls_R_factor_gt 0.1054 _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^)+(0.0630P)^2^+138.2162P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2633 _refine_ls_wR_factor_ref 0.2670 _reflns_Friedel_coverage 0.000 _reflns_number_gt 6412 _reflns_number_total 7306 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1sc03713g2.cif _cod_data_source_block 1-GuaCl _cod_original_sg_symbol_H-M 'R -3' _cod_database_code 1564359 _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 0.879 _shelx_estimated_absorpt_t_min 0.812 _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) groups, All C(H,H,H,H) groups, All N(H,H) groups 2. Restrained distances O1A-C1A \\sim O1A-C1 with sigma of 0.02 O00D-C21 \\sim O6A-C21 with sigma of 0.02 O1A-C1 \\sim O1-C1 with sigma of 0.02 O1A-C2 \\sim O1-C2 with sigma of 0.02 O1A-C1A \\sim O1-C1A with sigma of 0.02 Cl3-C24 \\sim Cl4-C24 \\sim Cl2-C24 with sigma of 0.02 Cl4-C24 \\sim Cl5-C24 with sigma of 0.02 Cl3-C24 \\sim Cl6-C24 with sigma of 0.02 3. Uiso/Uaniso restraints and constraints Uanis(Cl5) \\sim Ueq, Uanis(Cl6) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002 4. Others Sof(C1)=Sof(H1A)=Sof(H1B)=1-FVAR(1) Sof(C1A)=Sof(H1AA)=Sof(H1AB)=FVAR(1) Sof(H2BC)=Sof(H2BD)=Sof(O1)=1-FVAR(2) Sof(H2AA)=Sof(H2AB)=Sof(O1A)=FVAR(2) Sof(H22)=Sof(O6A)=1-FVAR(3) Sof(H22A)=Sof(H22B)=Sof(O00D)=FVAR(3) Sof(H24A)=Sof(Cl6)=1-FVAR(4) Sof(Cl3)=FVAR(4) Sof(Cl5)=1-FVAR(5) Sof(H24)=Sof(Cl4)=FVAR(5) Fixed Sof: H1C(0.91667) H1D(0.91667) 5.a Ternary CH refined with riding coordinates: C24(H24), C24(H24A) 5.b Secondary CH2 refined with riding coordinates: C2(H2AA,H2AB), C2(H2BC,H2BD), C3(H3A,H3B), C10(H10A,H10B), C13(H13A,H13B), C20(H20A,H20B), C22(H22A,H22B), C1A(H1AA,H1AB), C1(H1A,H1B) 5.c Aromatic/amide H refined with riding coordinates: C5(H5), C6(H6), C7(H7), C8(H8), C15(H15), C16(H16), C17(H17), C18(H18), C22(H22) 5.d X=CH2 refined with riding coordinates: N1(H1C,H1D) ; _shelx_res_file ; TITL R-3_a.res in R-3 r-3_a.res created by SHELXL-2018/3 at 15:08:34 on 06-Mar-2021 REM Old TITL R-3 in R-3 REM SHELXT solution in R-3 REM R1 0.323, Rweak 0.049, Alpha 0.061, Orientation as input REM Formula found by SHELXT: C140 Cl19 N12 O30 CELL 0.71073 21.6944 21.6944 27.4796 90 90 120 ZERR 3 0.0025 0.0025 0.0038 0 0 0 LATT 3 SYMM -Y,+X-Y,+Z SYMM +Y-X,-X,+Z SFAC C H Cl N O UNIT 420 473.88 57 18 108 SADI O1A C1A O1A C1 SADI O00D C21 O6A C21 SADI O1A C1 O1 C1 SADI O1A C2 O1 C2 SADI O1A C1A O1 C1A SADI Cl3 C24 Cl4 C24 Cl2 C24 SADI Cl4 C24 Cl5 C24 SADI Cl3 C24 Cl6 C24 ISOR 0.001 0.002 Cl5 Cl6 L.S. 10 PLAN 4 SIZE 0.311 0.359 0.51 TEMP -123 CONF BOND $H LIST 6 MORE -1 fmap 2 acta REM REM REM WGHT 0.063000 138.216187 FVAR 0.14866 0.40269 0.46865 0.52469 0.86187 0.83041 CL1 3 0.000000 0.000000 0.500000 10.16667 0.05623 0.05623 = 0.04532 0.00000 0.00000 0.02811 CL2 3 0.109405 0.106505 0.365365 11.00000 0.11854 0.09770 = 0.08612 -0.03586 0.01384 0.05796 C24 1 0.101667 0.139418 0.421541 11.00000 0.05546 0.05359 = 0.05218 -0.00205 0.00214 0.03942 PART 1 AFIX 13 H24 2 0.079586 0.099173 0.445307 61.00000 -1.20000 AFIX 13 PART 2 H24A 2 0.057920 0.101911 0.438195 -51.00000 -1.20000 AFIX 0 PART 1 CL3 3 0.049016 0.178678 0.417676 51.00000 0.08672 0.11226 = 0.11421 -0.05445 -0.04881 0.08229 CL4 3 0.188219 0.202820 0.442533 61.00000 0.04643 0.08920 = 0.07710 -0.01580 -0.00405 0.03953 PART 2 CL5 3 0.170359 0.172224 0.461896 -61.00000 0.08571 0.08736 = 0.08770 0.00157 -0.00174 0.04383 CL6 3 0.084300 0.204534 0.399195 -51.00000 0.06786 0.06866 = 0.06942 0.00081 -0.00363 0.03590 PART 0 O2 5 0.550138 0.420289 0.550727 11.00000 0.04427 0.04127 = 0.02531 -0.00921 -0.00980 0.02914 O3 5 0.533545 0.358254 0.468258 11.00000 0.02148 0.02936 = 0.02015 -0.00360 -0.00103 0.01703 O4 5 0.500567 0.184447 0.369518 11.00000 0.01877 0.01642 = 0.01990 0.00309 -0.00246 0.00204 O5 5 0.370606 0.139324 0.409200 11.00000 0.01994 0.02304 = 0.03999 0.00304 0.00766 0.00800 C2 1 0.638843 0.479140 0.610779 11.00000 0.04239 0.05583 = 0.02760 -0.00201 -0.00463 0.00912 PART 1 AFIX 23 H2AA 2 0.652515 0.509407 0.640248 31.00000 -1.20000 H2AB 2 0.639761 0.435041 0.618531 31.00000 -1.20000 AFIX 23 PART 2 H2BC 2 0.644740 0.496089 0.644831 -31.00000 -1.20000 H2BD 2 0.641069 0.434660 0.610891 -31.00000 -1.20000 AFIX 0 PART 0 C3 1 0.566906 0.461976 0.593838 11.00000 0.03471 0.04756 = 0.02269 -0.00830 0.00223 0.01114 AFIX 23 H3A 2 0.531186 0.435197 0.619371 11.00000 -1.20000 H3B 2 0.566162 0.506435 0.587133 11.00000 -1.20000 AFIX 0 C4 1 0.490975 0.408431 0.525063 11.00000 0.02697 0.02373 = 0.02066 0.00127 0.00219 0.01334 C5 1 0.441081 0.425976 0.540690 11.00000 0.03540 0.03007 = 0.02592 -0.00067 0.00861 0.01749 AFIX 43 H5 2 0.446898 0.448773 0.571232 11.00000 -1.20000 AFIX 0 C6 1 0.382469 0.410326 0.511807 11.00000 0.02735 0.03515 = 0.03779 -0.00219 0.00965 0.01860 AFIX 43 H6 2 0.348265 0.422361 0.522723 11.00000 -1.20000 AFIX 0 C7 1 0.373671 0.377271 0.467188 11.00000 0.01935 0.03625 = 0.04090 -0.00692 0.00091 0.01583 AFIX 43 H7 2 0.333429 0.366550 0.447615 11.00000 -1.20000 AFIX 0 C8 1 0.424045 0.359660 0.450930 11.00000 0.02102 0.02884 = 0.02564 -0.00492 0.00051 0.01423 AFIX 43 H8 2 0.418282 0.337371 0.420191 11.00000 -1.20000 AFIX 0 C9 1 0.482240 0.374761 0.479689 11.00000 0.01934 0.02161 = 0.02237 0.00263 0.00548 0.01186 C10 1 0.534479 0.336101 0.418945 11.00000 0.01853 0.02908 = 0.02192 -0.00572 -0.00299 0.01525 AFIX 23 H10A 2 0.533998 0.370454 0.395451 11.00000 -1.20000 H10B 2 0.492818 0.288498 0.412630 11.00000 -1.20000 AFIX 0 C11 1 0.602781 0.334092 0.414973 11.00000 0.01625 0.01839 = 0.01773 -0.00196 -0.00141 0.00983 C12 1 0.601499 0.269194 0.415070 11.00000 0.01623 0.01569 = 0.01599 0.00021 0.00121 0.00596 C13 1 0.531390 0.200038 0.417927 11.00000 0.01712 0.01864 = 0.02002 0.00085 0.00021 0.00434 AFIX 23 H13A 2 0.539223 0.161174 0.429265 11.00000 -1.20000 H13B 2 0.498993 0.204680 0.441091 11.00000 -1.20000 AFIX 0 C14 1 0.447018 0.115060 0.362948 11.00000 0.01924 0.01748 = 0.01902 0.00230 -0.00161 0.00400 C15 1 0.460554 0.069582 0.335904 11.00000 0.02970 0.02444 = 0.01694 0.00069 -0.00054 0.01104 AFIX 43 H15 2 0.507489 0.085182 0.324641 11.00000 -1.20000 AFIX 0 C16 1 0.405782 0.000531 0.324835 11.00000 0.04268 0.02342 = 0.02284 -0.00187 -0.00338 0.01250 AFIX 43 H16 2 0.415218 -0.030525 0.305969 11.00000 -1.20000 AFIX 0 C17 1 0.337956 -0.021585 0.341787 11.00000 0.03376 0.02325 = 0.03484 -0.00392 -0.01082 0.00057 AFIX 43 H17 2 0.300439 -0.068050 0.334121 11.00000 -1.20000 AFIX 0 C18 1 0.323749 0.023188 0.369935 11.00000 0.02170 0.02633 = 0.04024 0.00189 -0.00366 0.00323 AFIX 43 H18 2 0.276866 0.007043 0.381534 11.00000 -1.20000 AFIX 0 C19 1 0.378227 0.091739 0.381154 11.00000 0.01959 0.02113 = 0.02999 0.00301 -0.00136 0.00632 C20 1 0.309834 0.112378 0.440302 11.00000 0.01959 0.03139 = 0.04269 0.00677 0.00881 0.01057 AFIX 23 H20A 2 0.298626 0.065522 0.453665 11.00000 -1.20000 H20B 2 0.268004 0.106375 0.421824 11.00000 -1.20000 AFIX 0 C21 1 0.327155 0.165040 0.480888 11.00000 0.02959 0.03549 = 0.04052 0.00833 0.00891 0.02055 H21A 2 0.284989 0.153653 0.499260 11.00000 0.03274 H21B 2 0.345832 0.210676 0.467672 11.00000 0.03581 C22 1 0.400796 0.210443 0.549795 11.00000 0.04866 0.03927 = 0.04460 -0.00531 -0.00155 0.02970 PART 1 AFIX 43 H22 2 0.368753 0.223035 0.564110 -41.00000 -1.20000 AFIX 23 PART 2 H22A 2 0.365378 0.222191 0.562860 41.00000 -1.20000 H22B 2 0.439121 0.253289 0.533617 41.00000 -1.20000 AFIX 0 PART 1 O1A 5 0.685958 0.516085 0.571721 31.00000 0.01927 0.02410 = 0.01847 -0.00973 -0.00041 0.00747 O6A 5 0.387453 0.172921 0.506091 -41.00000 0.03840 0.05293 = 0.03659 -0.00996 -0.00349 0.02851 C1A 1 0.758905 0.530800 0.570964 21.00000 0.08293 0.07056 = 0.02979 0.01223 0.01704 0.05826 AFIX 23 H1AA 2 0.760757 0.492684 0.552356 21.00000 -1.20000 H1AB 2 0.773787 0.529037 0.604752 21.00000 -1.20000 AFIX 0 PART 2 O00D 5 0.367629 0.152922 0.515737 41.00000 0.02957 0.02357 = 0.04376 0.00532 0.00128 0.01577 O1 5 0.697258 0.530963 0.583077 -31.00000 0.03237 0.05564 = 0.05377 0.01032 -0.00658 0.01942 C1 1 0.755291 0.568449 0.590840 -21.00000 0.02828 0.04156 = 0.03507 -0.00142 -0.00575 0.00996 AFIX 23 H1A 2 0.771265 0.543437 0.613200 -21.00000 -1.20000 H1B 2 0.758374 0.609208 0.609140 -21.00000 -1.20000 AFIX 0 PART 0 N1 4 0.597993 0.311963 0.546131 11.00000 0.06239 0.07429 = 0.11048 0.01989 0.00372 0.03824 AFIX 93 H1C 2 0.566729 0.266429 0.549500 10.91667 -1.20000 H1D 2 0.583557 0.343275 0.544455 10.91667 -1.20000 AFIX 0 C23 1 0.666667 0.333333 0.543588 10.33333 0.05245 0.05245 = 0.04626 0.00000 0.00000 0.02623 HKLF 4 REM R-3_a.res in R-3 REM wR2 = 0.2670, GooF = S = 1.155, Restrained GooF = 1.157 for all data REM R1 = 0.1054 for 6412 Fo > 4sig(Fo) and 0.1128 for all 7306 data REM 361 parameters refined using 24 restraints END WGHT 0.0631 138.1325 REM Highest difference peak 0.526, deepest hole -0.990, 1-sigma level 0.105 Q1 1 0.1223 0.2416 0.3739 11.00000 0.05 0.53 Q2 1 0.3247 0.1321 0.4686 11.00000 0.05 0.43 Q3 1 0.1800 0.1698 0.4004 11.00000 0.05 0.41 Q4 1 0.2629 -0.0877 0.3354 11.00000 0.05 0.40 ; _shelx_res_checksum 56526 _olex2_submission_special_instructions 'No special instructions were received' 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 Cl1 Cl 0.000000 0.000000 0.500000 0.0526(7) Uani 1 6 d S T P . . Cl2 Cl 0.10941(14) 0.10651(13) 0.36536(8) 0.0991(8) Uani 1 1 d D . . . . C24 C 0.1017(3) 0.1394(3) 0.42154(19) 0.0483(11) Uani 1 1 d D . . . . H24 H 0.079586 0.099173 0.445307 0.058 Uiso 0.830(11) 1 calc R U P A 1 H24A H 0.057920 0.101911 0.438195 0.058 Uiso 0.138(12) 1 calc R U P A 2 Cl3 Cl 0.0490(2) 0.1787(2) 0.41768(16) 0.0899(17) Uani 0.862(12) 1 d D . P A 1 Cl4 Cl 0.18822(12) 0.20282(19) 0.44253(12) 0.0684(11) Uani 0.830(11) 1 d D . P A 1 Cl5 Cl 0.1704(9) 0.1722(11) 0.4619(7) 0.087(5) Uani 0.170(11) 1 d D U P A 2 Cl6 Cl 0.0843(12) 0.2045(8) 0.3992(6) 0.068(5) Uani 0.138(12) 1 d D U P A 2 O2 O 0.55014(16) 0.42029(16) 0.55073(10) 0.0335(6) Uani 1 1 d . . . . . O3 O 0.53355(12) 0.35825(13) 0.46826(8) 0.0217(5) Uani 1 1 d . . . . . O4 O 0.50057(12) 0.18445(12) 0.36952(8) 0.0214(5) Uani 1 1 d . . . . . O5 O 0.37061(13) 0.13932(14) 0.40920(10) 0.0289(5) Uani 1 1 d . . . . . C2 C 0.6388(3) 0.4791(3) 0.61078(16) 0.0488(12) Uani 1 1 d D . . . . H2AA H 0.652515 0.509407 0.640248 0.059 Uiso 0.47(10) 1 calc R U P B 1 H2AB H 0.639761 0.435041 0.618531 0.059 Uiso 0.47(10) 1 calc R U P B 1 H2BC H 0.644740 0.496089 0.644831 0.059 Uiso 0.53(10) 1 calc R U P B 2 H2BD H 0.641069 0.434660 0.610891 0.059 Uiso 0.53(10) 1 calc R U P B 2 C3 C 0.5669(2) 0.4620(3) 0.59384(14) 0.0392(10) Uani 1 1 d . . . . . H3A H 0.531186 0.435197 0.619371 0.047 Uiso 1 1 calc R U . . . H3B H 0.566162 0.506435 0.587133 0.047 Uiso 1 1 calc R U . . . C4 C 0.49098(19) 0.40843(18) 0.52506(12) 0.0235(6) Uani 1 1 d . . . . . C5 C 0.4411(2) 0.4260(2) 0.54069(14) 0.0300(7) Uani 1 1 d . . . . . H5 H 0.446898 0.448773 0.571232 0.036 Uiso 1 1 calc R U . . . C6 C 0.3825(2) 0.4103(2) 0.51181(15) 0.0321(8) Uani 1 1 d . . . . . H6 H 0.348265 0.422361 0.522723 0.039 Uiso 1 1 calc R U . . . C7 C 0.37367(19) 0.3773(2) 0.46719(15) 0.0313(8) Uani 1 1 d . . . . . H7 H 0.333429 0.366550 0.447615 0.038 Uiso 1 1 calc R U . . . C8 C 0.42405(18) 0.35966(19) 0.45093(13) 0.0244(6) Uani 1 1 d . . . . . H8 H 0.418282 0.337371 0.420191 0.029 Uiso 1 1 calc R U . . . C9 C 0.48224(17) 0.37476(17) 0.47969(12) 0.0204(6) Uani 1 1 d . . . . . C10 C 0.53448(17) 0.33610(18) 0.41894(12) 0.0217(6) Uani 1 1 d . . . . . H10A H 0.533998 0.370454 0.395451 0.026 Uiso 1 1 calc R U . . . H10B H 0.492818 0.288498 0.412630 0.026 Uiso 1 1 calc R U . . . C11 C 0.60278(16) 0.33409(16) 0.41497(11) 0.0169(5) Uani 1 1 d . . . . . C12 C 0.60150(16) 0.26919(16) 0.41507(11) 0.0169(5) Uani 1 1 d . . . . . C13 C 0.53139(17) 0.20004(17) 0.41793(11) 0.0206(6) Uani 1 1 d . . . . . H13A H 0.539223 0.161174 0.429265 0.025 Uiso 1 1 calc R U . . . H13B H 0.498993 0.204680 0.441091 0.025 Uiso 1 1 calc R U . . . C14 C 0.44702(17) 0.11506(17) 0.36295(11) 0.0209(6) Uani 1 1 d . . . . . C15 C 0.46055(19) 0.06958(18) 0.33590(12) 0.0248(6) Uani 1 1 d . . . . . H15 H 0.507489 0.085182 0.324641 0.030 Uiso 1 1 calc R U . . . C16 C 0.4058(2) 0.0005(2) 0.32484(13) 0.0314(8) Uani 1 1 d . . . . . H16 H 0.415218 -0.030525 0.305969 0.038 Uiso 1 1 calc R U . . . C17 C 0.3380(2) -0.0216(2) 0.34179(15) 0.0367(9) Uani 1 1 d . . . . . H17 H 0.300439 -0.068050 0.334121 0.044 Uiso 1 1 calc R U . . . C18 C 0.3237(2) 0.0232(2) 0.36994(16) 0.0333(8) Uani 1 1 d . . . . . H18 H 0.276866 0.007043 0.381534 0.040 Uiso 1 1 calc R U . . . C19 C 0.37823(18) 0.09174(18) 0.38115(13) 0.0253(7) Uani 1 1 d . . . . . C20 C 0.30983(19) 0.1124(2) 0.44030(16) 0.0322(8) Uani 1 1 d . . . . . H20A H 0.298626 0.065522 0.453665 0.039 Uiso 1 1 calc R U . . . H20B H 0.268004 0.106375 0.421824 0.039 Uiso 1 1 calc R U . . . C21 C 0.3272(2) 0.1650(2) 0.48089(16) 0.0333(8) Uani 1 1 d D . . . . H21A H 0.285(3) 0.154(3) 0.4993(18) 0.033(12) Uiso 1 1 d . . . . . H21B H 0.346(3) 0.211(3) 0.4677(18) 0.036(13) Uiso 1 1 d . . . . . C22 C 0.4008(3) 0.2104(2) 0.54980(18) 0.0407(10) Uani 1 1 d . . . . . H22 H 0.368753 0.223035 0.564110 0.049 Uiso 0.48(7) 1 calc R U P C 1 H22A H 0.365378 0.222191 0.562860 0.049 Uiso 0.52(7) 1 calc R U P C 2 H22B H 0.439121 0.253289 0.533617 0.049 Uiso 0.52(7) 1 calc R U P C 2 O1A O 0.6860(12) 0.5161(8) 0.5717(6) 0.022(4) Uani 0.47(10) 1 d D . P B 1 O6A O 0.3875(16) 0.173(2) 0.5061(9) 0.040(5) Uani 0.48(7) 1 d D . P C 1 C1A C 0.7589(8) 0.5308(8) 0.5710(4) 0.052(4) Uani 0.403(16) 1 d . . P B 1 H1AA H 0.760757 0.492684 0.552356 0.063 Uiso 0.403(16) 1 calc R U P B 1 H1AB H 0.773787 0.529037 0.604752 0.063 Uiso 0.403(16) 1 calc R U P B 1 O00D O 0.3676(13) 0.1529(8) 0.5157(7) 0.031(3) Uani 0.52(7) 1 d D . P C 2 O1 O 0.6973(12) 0.531(2) 0.5831(17) 0.048(5) Uani 0.53(10) 1 d D . P B 2 C1 C 0.7553(4) 0.5684(4) 0.5908(3) 0.038(2) Uani 0.597(16) 1 d . . P B 2 H1A H 0.771265 0.543437 0.613200 0.046 Uiso 0.597(16) 1 calc R U P B 2 H1B H 0.758374 0.609208 0.609140 0.046 Uiso 0.597(16) 1 calc R U P B 2 N1 N 0.5980(3) 0.3120(3) 0.5461(3) 0.0806(18) Uani 1 1 d . . . . . H1C H 0.566729 0.266429 0.549500 0.097 Uiso 0.9167 1 calc R U P . . H1D H 0.583557 0.343275 0.544455 0.097 Uiso 0.9167 1 calc R U P . . C23 C 0.666667 0.333333 0.5436(3) 0.050(2) Uani 1 3 d S T P . . 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 Cl1 0.0562(11) 0.0562(11) 0.0453(15) 0.000 0.000 0.0281(5) Cl2 0.1185(18) 0.0977(15) 0.0861(14) -0.0359(11) 0.0138(12) 0.0580(14) C24 0.055(3) 0.054(3) 0.052(3) -0.002(2) 0.002(2) 0.039(3) Cl3 0.087(2) 0.112(3) 0.114(3) -0.054(2) -0.049(2) 0.082(2) Cl4 0.0464(11) 0.089(2) 0.0771(17) -0.0158(14) -0.0040(9) 0.0395(12) Cl5 0.086(5) 0.087(5) 0.088(5) 0.002(2) -0.0017(19) 0.044(3) Cl6 0.068(5) 0.069(5) 0.069(5) 0.0008(19) -0.0036(19) 0.036(3) O2 0.0443(16) 0.0413(15) 0.0253(13) -0.0092(11) -0.0098(11) 0.0291(14) O3 0.0215(11) 0.0294(12) 0.0202(10) -0.0036(9) -0.0010(8) 0.0170(10) O4 0.0188(10) 0.0164(10) 0.0199(10) 0.0031(8) -0.0025(8) 0.0020(8) O5 0.0199(11) 0.0230(12) 0.0400(15) 0.0030(10) 0.0077(10) 0.0080(10) C2 0.042(2) 0.056(3) 0.028(2) -0.0020(19) -0.0046(17) 0.009(2) C3 0.035(2) 0.048(2) 0.0227(17) -0.0083(16) 0.0022(15) 0.0111(18) C4 0.0270(16) 0.0237(15) 0.0207(14) 0.0013(11) 0.0022(12) 0.0133(13) C5 0.0354(19) 0.0301(17) 0.0259(16) -0.0007(13) 0.0086(14) 0.0175(15) C6 0.0274(17) 0.0352(19) 0.038(2) -0.0022(15) 0.0096(15) 0.0186(15) C7 0.0194(15) 0.0363(19) 0.041(2) -0.0069(16) 0.0009(14) 0.0158(14) C8 0.0210(14) 0.0288(16) 0.0256(15) -0.0049(12) 0.0005(12) 0.0142(13) C9 0.0193(14) 0.0216(14) 0.0224(14) 0.0026(11) 0.0055(11) 0.0119(12) C10 0.0185(13) 0.0291(16) 0.0219(14) -0.0057(12) -0.0030(11) 0.0152(12) C11 0.0163(12) 0.0184(13) 0.0177(12) -0.0020(10) -0.0014(10) 0.0098(11) C12 0.0162(12) 0.0157(12) 0.0160(12) 0.0002(10) 0.0012(10) 0.0060(10) C13 0.0171(13) 0.0186(13) 0.0200(14) 0.0008(11) 0.0002(10) 0.0043(11) C14 0.0192(14) 0.0175(13) 0.0190(13) 0.0023(10) -0.0016(11) 0.0040(11) C15 0.0297(17) 0.0244(15) 0.0169(14) 0.0007(11) -0.0005(12) 0.0110(13) C16 0.043(2) 0.0234(16) 0.0228(16) -0.0019(12) -0.0034(14) 0.0125(15) C17 0.034(2) 0.0232(17) 0.035(2) -0.0039(14) -0.0108(16) 0.0006(15) C18 0.0217(16) 0.0263(17) 0.040(2) 0.0019(15) -0.0037(14) 0.0032(14) C19 0.0196(14) 0.0211(15) 0.0300(17) 0.0030(12) -0.0014(12) 0.0063(12) C20 0.0196(15) 0.0314(18) 0.043(2) 0.0068(15) 0.0088(14) 0.0106(14) C21 0.0296(18) 0.035(2) 0.041(2) 0.0083(16) 0.0089(16) 0.0205(16) C22 0.049(2) 0.039(2) 0.045(2) -0.0053(18) -0.0016(19) 0.030(2) O1A 0.019(5) 0.024(5) 0.018(5) -0.010(3) 0.000(3) 0.007(3) O6A 0.038(7) 0.053(12) 0.037(6) -0.010(6) -0.003(5) 0.029(8) C1A 0.083(10) 0.071(9) 0.030(6) 0.012(6) 0.017(6) 0.058(8) O00D 0.030(5) 0.024(4) 0.044(5) 0.005(3) 0.001(4) 0.016(4) O1 0.032(5) 0.056(10) 0.054(10) 0.010(10) -0.007(7) 0.019(5) C1 0.028(3) 0.042(4) 0.035(4) -0.001(3) -0.006(3) 0.010(3) N1 0.062(3) 0.074(4) 0.110(5) 0.020(4) 0.004(3) 0.038(3) C23 0.052(3) 0.052(3) 0.046(5) 0.000 0.000 0.0262(15) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 '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 Cl2 C24 H24 108.8 . . ? Cl2 C24 H24A 108.6 . . ? Cl2 C24 Cl4 108.8(3) . . ? Cl2 C24 Cl6 97.1(6) . . ? Cl3 C24 Cl2 111.6(3) . . ? Cl3 C24 H24 108.8 . . ? Cl3 C24 Cl4 109.8(3) . . ? Cl4 C24 H24 108.8 . . ? Cl5 C24 Cl2 120.3(7) . . ? Cl5 C24 H24A 108.6 . . ? Cl5 C24 Cl6 112.9(9) . . ? Cl6 C24 H24A 108.6 . . ? C4 O2 C3 117.7(3) . . ? C9 O3 C10 116.9(2) . . ? C14 O4 C13 114.4(2) . . ? C19 O5 C20 117.7(3) . . ? H2AA C2 H2AB 108.7 . . ? H2BC C2 H2BD 107.4 . . ? C3 C2 H2AA 110.6 . . ? C3 C2 H2AB 110.6 . . ? C3 C2 H2BC 108.3 . . ? C3 C2 H2BD 108.3 . . ? O1A C2 H2AA 110.6 . . ? O1A C2 H2AB 110.6 . . ? O1A C2 C3 105.9(11) . . ? O1 C2 H2BC 108.3 . . ? O1 C2 H2BD 108.3 . . ? O1 C2 C3 116.0(11) . . ? O2 C3 C2 108.8(4) . . ? O2 C3 H3A 109.9 . . ? O2 C3 H3B 109.9 . . ? C2 C3 H3A 109.9 . . ? C2 C3 H3B 109.9 . . ? H3A C3 H3B 108.3 . . ? O2 C4 C5 125.2(3) . . ? O2 C4 C9 115.0(3) . . ? C5 C4 C9 119.8(3) . . ? C4 C5 H5 119.9 . . ? C4 C5 C6 120.1(3) . . ? C6 C5 H5 119.9 . . ? C5 C6 H6 119.8 . . ? C7 C6 C5 120.3(3) . . ? C7 C6 H6 119.8 . . ? C6 C7 H7 120.0 . . ? C6 C7 C8 120.0(4) . . ? C8 C7 H7 120.0 . . ? C7 C8 H8 120.1 . . ? C9 C8 C7 119.9(3) . . ? C9 C8 H8 120.1 . . ? O3 C9 C4 115.1(3) . . ? O3 C9 C8 125.0(3) . . ? C8 C9 C4 119.9(3) . . ? O3 C10 H10A 110.8 . . ? O3 C10 H10B 110.8 . . ? O3 C10 C11 104.8(2) . . ? H10A C10 H10B 108.9 . . ? C11 C10 H10A 110.8 . . ? C11 C10 H10B 110.8 . . ? C12 C11 C10 120.4(3) . . ? C12 C11 C10 118.9(3) 3_665 . ? C12 C11 C12 120.6(3) . 3_665 ? C11 C12 C11 119.4(3) . 2_655 ? C11 C12 C13 120.3(3) . . ? C11 C12 C13 120.3(3) 2_655 . ? O4 C13 C12 107.5(2) . . ? O4 C13 H13A 110.2 . . ? O4 C13 H13B 110.2 . . ? C12 C13 H13A 110.2 . . ? C12 C13 H13B 110.2 . . ? H13A C13 H13B 108.5 . . ? O4 C14 C15 119.2(3) . . ? O4 C14 C19 120.6(3) . . ? C15 C14 C19 120.1(3) . . ? C14 C15 H15 119.6 . . ? C14 C15 C16 120.7(3) . . ? C16 C15 H15 119.6 . . ? C15 C16 H16 120.5 . . ? C17 C16 C15 119.0(4) . . ? C17 C16 H16 120.5 . . ? C16 C17 H17 119.5 . . ? C16 C17 C18 121.0(3) . . ? C18 C17 H17 119.5 . . ? C17 C18 H18 119.9 . . ? C17 C18 C19 120.1(4) . . ? C19 C18 H18 119.9 . . ? O5 C19 C14 115.9(3) . . ? O5 C19 C18 125.0(3) . . ? C18 C19 C14 119.1(3) . . ? O5 C20 H20A 110.2 . . ? O5 C20 H20B 110.2 . . ? O5 C20 C21 107.7(3) . . ? H20A C20 H20B 108.5 . . ? C21 C20 H20A 110.2 . . ? C21 C20 H20B 110.2 . . ? C20 C21 H21A 110(3) . . ? C20 C21 H21B 109(3) . . ? H21A C21 H21B 109(4) . . ? O6A C21 C20 108.7(7) . . ? O6A C21 H21A 119(3) . . ? O6A C21 H21B 100(4) . . ? O00D C21 C20 107.7(6) . . ? O00D C21 H21A 101(3) . . ? O00D C21 H21B 119(3) . . ? H22A C22 H22B 108.5 . . ? O6A C22 H22 123.7 . . ? O6A C22 C1A 112.6(9) . 2_655 ? O6A C22 C1 116.0(12) . 2_655 ? C1A C22 H22 123.7 2_655 . ? C1A C22 C1 39.9(6) 2_655 2_655 ? O00D C22 H22A 110.2 . . ? O00D C22 H22B 110.2 . . ? C1 C22 H22A 110.2 2_655 . ? C1 C22 H22B 110.2 2_655 . ? C2 O1A C1A 122.2(16) . . ? C22 O6A C21 113.7(9) . . ? C22 C1A H1AA 108.6 3_665 . ? C22 C1A H1AB 108.6 3_665 . ? O1A C1A C22 114.6(10) . 3_665 ? O1A C1A H1AA 108.6 . . ? O1A C1A H1AB 108.6 . . ? H1AA C1A H1AB 107.6 . . ? C21 O00D C22 111.7(7) . . ? C1 O1 C2 135(3) . . ? C22 C1 H1A 107.0 3_665 . ? C22 C1 H1B 107.0 3_665 . ? O1 C1 H1A 107.0 . . ? O1 C1 H1B 107.0 . . ? H1A C1 H1B 106.8 . . ? H1C N1 H1D 120.0 . . ? C23 N1 H1C 120.0 . . ? C23 N1 H1D 120.0 . . ? N1 C23 N1 119.72(10) 2_655 3_665 ? N1 C23 N1 119.73(10) 3_665 . ? N1 C23 N1 119.72(10) 2_655 . ? 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 Cl2 C24 1.744(5) . ? C24 H24 1.0000 . ? C24 H24A 1.0000 . ? C24 Cl3 1.736(5) . ? C24 Cl4 1.780(6) . ? C24 Cl5 1.702(11) . ? C24 Cl6 1.746(12) . ? O2 C3 1.423(5) . ? O2 C4 1.371(4) . ? O3 C9 1.365(4) . ? O3 C10 1.441(4) . ? O4 C13 1.451(4) . ? O4 C14 1.378(4) . ? O5 C19 1.363(4) . ? O5 C20 1.428(4) . ? C2 H2AA 0.9900 . ? C2 H2AB 0.9900 . ? C2 H2BC 0.9900 . ? C2 H2BD 0.9900 . ? C2 C3 1.487(7) . ? C2 O1A 1.421(10) . ? C2 O1 1.423(11) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.383(5) . ? C4 C9 1.409(5) . ? C5 H5 0.9500 . ? C5 C6 1.389(6) . ? C6 H6 0.9500 . ? C6 C7 1.385(5) . ? C7 H7 0.9500 . ? C7 C8 1.399(5) . ? C8 H8 0.9500 . ? C8 C9 1.383(5) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C10 C11 1.508(4) . ? C11 C12 1.403(4) 3_665 ? C11 C12 1.394(4) . ? C12 C13 1.513(4) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.379(5) . ? C14 C19 1.407(5) . ? C15 H15 0.9500 . ? C15 C16 1.403(5) . ? C16 H16 0.9500 . ? C16 C17 1.381(6) . ? C17 H17 0.9500 . ? C17 C18 1.391(6) . ? C18 H18 0.9500 . ? C18 C19 1.395(5) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C20 C21 1.504(6) . ? C21 H21A 0.96(5) . ? C21 H21B 0.94(5) . ? C21 O6A 1.413(10) . ? C21 O00D 1.410(9) . ? C22 H22 0.9500 . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C22 O6A 1.398(13) . ? C22 C1A 1.456(15) 2_655 ? C22 O00D 1.433(12) . ? C22 C1 1.524(9) 2_655 ? O1A C1A 1.45(3) . ? C1A H1AA 0.9900 . ? C1A H1AB 0.9900 . ? O1 C1 1.13(4) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? N1 H1C 0.8800 . ? N1 H1D 0.8800 . ? N1 C23 1.322(6) . ? 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 O2 C4 C5 C6 -179.0(4) . . . . ? O2 C4 C9 O3 0.7(4) . . . . ? O2 C4 C9 C8 179.4(3) . . . . ? O3 C10 C11 C12 104.5(3) . . . . ? O3 C10 C11 C12 -70.5(3) . . . 3_665 ? O4 C14 C15 C16 -174.3(3) . . . . ? O4 C14 C19 O5 -6.3(5) . . . . ? O4 C14 C19 C18 174.0(3) . . . . ? O5 C20 C21 O6A -59(2) . . . . ? O5 C20 C21 O00D -80.9(12) . . . . ? C2 O1A C1A C22 -143.6(11) . . . 3_665 ? C2 O1 C1 C22 159(4) . . . 3_665 ? C3 O2 C4 C5 -8.6(5) . . . . ? C3 O2 C4 C9 172.2(3) . . . . ? C3 C2 O1A C1A -168.9(13) . . . . ? C3 C2 O1 C1 156(4) . . . . ? C4 O2 C3 C2 -169.9(4) . . . . ? C4 C5 C6 C7 -0.2(6) . . . . ? C5 C4 C9 O3 -178.5(3) . . . . ? C5 C4 C9 C8 0.2(5) . . . . ? C5 C6 C7 C8 -0.2(6) . . . . ? C6 C7 C8 C9 0.6(6) . . . . ? C7 C8 C9 O3 178.0(3) . . . . ? C7 C8 C9 C4 -0.6(5) . . . . ? C9 O3 C10 C11 170.5(3) . . . . ? C9 C4 C5 C6 0.1(5) . . . . ? C10 O3 C9 C4 -168.8(3) . . . . ? C10 O3 C9 C8 12.5(5) . . . . ? C10 C11 C12 C11 -175.3(2) . . . 2_655 ? C10 C11 C12 C13 1.5(4) . . . . ? C11 C12 C13 O4 -103.3(3) 2_655 . . . ? C11 C12 C13 O4 79.9(3) . . . . ? C12 C11 C12 C11 -0.4(6) 3_665 . . 2_655 ? C12 C11 C12 C13 176.4(2) 3_665 . . . ? C13 O4 C14 C15 -106.2(3) . . . . ? C13 O4 C14 C19 77.4(4) . . . . ? C14 O4 C13 C12 163.5(3) . . . . ? C14 C15 C16 C17 -0.5(5) . . . . ? C15 C14 C19 O5 177.3(3) . . . . ? C15 C14 C19 C18 -2.3(5) . . . . ? C15 C16 C17 C18 -0.8(6) . . . . ? C16 C17 C18 C19 0.5(6) . . . . ? C17 C18 C19 O5 -178.5(4) . . . . ? C17 C18 C19 C14 1.1(6) . . . . ? C19 O5 C20 C21 156.7(3) . . . . ? C19 C14 C15 C16 2.1(5) . . . . ? C20 O5 C19 C14 -161.1(3) . . . . ? C20 O5 C19 C18 18.6(5) . . . . ? C20 C21 O6A C22 -169(2) . . . . ? C20 C21 O00D C22 166.2(14) . . . . ? O1A C2 C3 O2 58.5(8) . . . . ? C1A C22 O6A C21 -170(2) 2_655 . . . ? O1 C2 C3 O2 74(3) . . . . ? C1 C22 O00D C21 169.8(14) 2_655 . . . ?