#------------------------------------------------------------------------------ #$Date: 2021-08-13 01:23:18 +0300 (Fri, 13 Aug 2021) $ #$Revision: 268055 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/56/43/1564357.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_1564357 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(I), 6(C H Cl3), 2(C67 H77.5 N3 O18)' _chemical_formula_sum 'C140 H161 Cl18 I N6 O36' _chemical_formula_weight 3268.74 _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 21.738(3) _cell_length_b 21.738(3) _cell_length_c 27.712(5) _cell_measurement_reflns_used 1003 _cell_measurement_temperature 150.15 _cell_measurement_theta_max 20.35 _cell_measurement_theta_min 2.20 _cell_volume 11341(3) _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 0.998 _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 0.0473 _diffrn_reflns_av_unetI/netI 0.0324 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_number 40495 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.295 _diffrn_reflns_theta_min 2.205 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.607 _exptl_absorpt_correction_type none _exptl_crystal_density_diffrn 1.436 _exptl_crystal_description bulk _exptl_crystal_F_000 5070 _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.332 _exptl_crystal_size_min 0.315 _refine_diff_density_max 1.205 _refine_diff_density_min -1.822 _refine_diff_density_rms 0.128 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.113 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 323 _refine_ls_number_reflns 6249 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.113 _refine_ls_R_factor_all 0.1106 _refine_ls_R_factor_gt 0.1032 _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^)+(0.0968P)^2^+164.8354P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2752 _refine_ls_wR_factor_ref 0.2797 _reflns_Friedel_coverage 0.000 _reflns_number_gt 5530 _reflns_number_total 6249 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1sc03713g2.cif _cod_data_source_block GuaI _cod_original_cell_volume 11341(4) _cod_original_sg_symbol_H-M 'R -3' _cod_database_code 1564357 _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 0.832 _shelx_estimated_absorpt_t_min 0.820 _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 O5A-C18 \\sim O5-C18 with sigma of 0.02 C20-C19A \\sim C20-C19 with sigma of 0.02 O5A-C19A \\sim O5-C19A with sigma of 0.02 O5A-C19A \\sim O5A-C19 with sigma of 0.02 3. Uiso/Uaniso restraints and constraints Cl2 \\sim Cl1 \\sim Cl3: within 2A with sigma of 0.001 and sigma for terminal atoms of 0.002 within 2A 4. Rigid body (RIGU) restrains Cl2 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002 5. Others Sof(H18C)=Sof(H18D)=Sof(O5)=1-FVAR(1) Sof(H18A)=Sof(H18B)=Sof(O5A)=FVAR(1) Sof(H20C)=Sof(H20D)=Sof(C19)=Sof(H19C)=Sof(H19D)=1-FVAR(2) Sof(H20A)=Sof(H20B)=Sof(C19A)=Sof(H19A)=Sof(H19B)=FVAR(2) Fixed Sof: H1A(0.91667) H1B(0.91667) 6.a Ternary CH refined with riding coordinates: C23(H23) 6.b Secondary CH2 refined with riding coordinates: C7(H7A,H7B), C10(H10A,H10B), C17(H17A,H17B), C18(H18A,H18B), C18(H18C,H18D), C20(H20A,H20B), C20(H20C,H20D), C21(H21A,H21B), C22(H22A,H22B), C19A(H19A, H19B), C19(H19C,H19D) 6.c Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C13(H13), C14(H14), C15(H15) 6.d X=CH2 refined with riding coordinates: N1(H1A,H1B) ; _shelx_res_file ; TITL R-3_a.res in R-3 r-3_a.res created by SHELXL-2018/3 at 15:49:08 on 06-Mar-2021 REM Old TITL R-3 in R-3 REM SHELXT solution in R-3 REM R1 0.305, Rweak 0.047, Alpha 0.054, Orientation as input REM Formula found by SHELXT: C140 F30 N12 O18 Br CELL 0.71073 21.7379 21.7379 27.7122 90 90 120 ZERR 3 0.0029 0.0029 0.0048 0 0 0 LATT 3 SYMM -Y,+X-Y,+Z SYMM +Y-X,-X,+Z SFAC C H Cl I N O UNIT 420 483 54 3 18 108 SADI O5A C18 O5 C18 SADI C20 C19A C20 C19 SADI O5A C19A O5 C19A SADI O5A C19A O5A C19 SIMU 0.001 0.002 2 Cl2 Cl1 Cl3 RIGU 0.001 0.002 Cl2 L.S. 20 PLAN 10 SIZE 0.315 0.332 0.34 TEMP -123 CONF BOND $H LIST 6 MORE -1 fmap 2 acta REM REM REM WGHT 0.096800 164.835403 FVAR 0.13921 0.45793 0.57866 I1 4 0.666667 0.333333 0.333333 10.16667 0.09377 0.09377 = 0.04163 0.00000 0.00000 0.04689 CL1 3 0.775849 0.452013 0.468280 11.00000 0.10279 0.12365 = 0.09673 -0.01204 0.04674 0.05826 CL2 3 0.865698 0.403983 0.431024 11.00000 0.18949 0.22972 = 0.19790 0.15988 0.12902 0.18715 CL3 3 0.873932 0.527198 0.391636 11.00000 0.12022 0.06281 = 0.09137 0.01710 0.03725 0.05944 O1 6 0.564118 0.526708 0.756847 11.00000 0.02798 0.02311 = 0.03947 0.00427 -0.00257 0.01580 O2 6 0.648415 0.481126 0.796539 11.00000 0.03260 0.01679 = 0.01949 0.00273 0.00507 0.01528 O3 6 0.799800 0.491885 0.698898 11.00000 0.02104 0.01475 = 0.01993 0.00269 -0.00049 0.00300 O4 6 0.783769 0.536891 0.616941 11.00000 0.04156 0.02685 = 0.02716 -0.00054 -0.01147 0.01280 O6 6 0.548710 0.506502 0.655134 11.00000 0.02457 0.07328 = 0.05831 -0.02629 0.00315 0.00905 N1 5 0.619356 0.355105 0.621200 11.00000 0.06356 0.06504 = 0.10294 0.01089 0.01081 0.03591 AFIX 93 H1A 2 0.573886 0.323876 0.618055 10.91667 -1.20000 H1B 2 0.633556 0.400722 0.622766 10.91667 -1.20000 AFIX 0 C00Y 1 0.666667 0.333333 0.623588 10.33333 0.05092 0.05092 = 0.04906 0.00000 0.00000 0.02546 C1 1 0.619401 0.574039 0.784822 11.00000 0.02886 0.02129 = 0.02705 0.00333 0.00626 0.01456 C2 1 0.633416 0.642668 0.796103 11.00000 0.04571 0.02685 = 0.04024 0.00394 0.00890 0.02557 AFIX 43 H2 2 0.602752 0.658802 0.784613 11.00000 -1.20000 AFIX 0 C3 1 0.691934 0.687053 0.823995 11.00000 0.05746 0.02184 = 0.03435 -0.00339 0.00902 0.02012 AFIX 43 H3 2 0.700860 0.733384 0.831729 11.00000 -1.20000 AFIX 0 C4 1 0.737298 0.664842 0.840637 11.00000 0.04474 0.02565 = 0.02178 -0.00313 0.00320 0.01024 AFIX 43 H4 2 0.777852 0.695952 0.859185 11.00000 -1.20000 AFIX 0 C5 1 0.723155 0.595912 0.829987 11.00000 0.03320 0.02535 = 0.01578 0.00027 0.00178 0.01318 AFIX 43 H5 2 0.754232 0.580187 0.841305 11.00000 -1.20000 AFIX 0 C6 1 0.664265 0.551001 0.803139 11.00000 0.02998 0.01770 = 0.01716 0.00154 0.00552 0.01253 C7 1 0.664041 0.465936 0.748681 11.00000 0.02404 0.01864 = 0.01999 0.00120 0.00095 0.01349 AFIX 23 H7A 2 0.710634 0.504957 0.737623 11.00000 -1.20000 H7B 2 0.627179 0.461305 0.725617 11.00000 -1.20000 AFIX 0 C8 1 0.665388 0.397126 0.751214 11.00000 0.01994 0.01485 = 0.01735 -0.00051 -0.00201 0.00982 C9 1 0.730488 0.398307 0.751248 11.00000 0.01538 0.01785 = 0.01641 -0.00002 -0.00211 0.00669 C10 1 0.798393 0.468438 0.747573 11.00000 0.01863 0.01765 = 0.02000 0.00273 -0.00189 0.00386 AFIX 23 H10A 2 0.798593 0.502971 0.770953 11.00000 -1.20000 H10B 2 0.839992 0.462585 0.753943 11.00000 -1.20000 AFIX 0 C11 1 0.851590 0.559800 0.687498 11.00000 0.01772 0.01624 = 0.02211 0.00197 0.00513 0.00676 C12 1 0.909207 0.602387 0.716041 11.00000 0.02067 0.02438 = 0.02665 0.00575 -0.00134 0.00898 AFIX 43 H12 2 0.914514 0.585852 0.746629 11.00000 -1.20000 AFIX 0 C13 1 0.960062 0.670175 0.699965 11.00000 0.01933 0.02699 = 0.04105 0.00584 -0.00052 0.00412 AFIX 43 H13 2 1.000137 0.699547 0.719470 11.00000 -1.20000 AFIX 0 C14 1 0.951691 0.694105 0.655666 11.00000 0.02662 0.02541 = 0.03956 0.01287 0.00998 0.00997 AFIX 43 H14 2 0.986136 0.740138 0.644853 11.00000 -1.20000 AFIX 0 C15 1 0.893669 0.651774 0.626827 11.00000 0.03314 0.02963 = 0.02436 0.00953 0.00675 0.01517 AFIX 43 H15 2 0.888360 0.668717 0.596399 11.00000 -1.20000 AFIX 0 C16 1 0.843074 0.584229 0.642576 11.00000 0.02786 0.02437 = 0.01881 0.00079 0.00202 0.01474 C17 1 0.767798 0.562782 0.574167 11.00000 0.03072 0.05569 = 0.02332 0.00919 0.00303 0.02121 AFIX 23 H17A 2 0.803409 0.571544 0.548856 11.00000 -1.20000 H17B 2 0.768910 0.608032 0.580989 11.00000 -1.20000 AFIX 0 C18 1 0.695220 0.507898 0.557342 11.00000 0.03473 0.07920 = 0.02903 -0.00461 -0.00701 0.02646 PART 1 AFIX 23 H18A 2 0.681461 0.524644 0.528266 21.00000 -1.20000 H18B 2 0.694044 0.462893 0.549489 21.00000 -1.20000 AFIX 23 PART 2 H18C 2 0.689362 0.519700 0.523773 -21.00000 -1.20000 H18D 2 0.693544 0.461556 0.556413 -21.00000 -1.20000 AFIX 0 PART 0 C20 1 0.524794 0.455091 0.618338 11.00000 0.03197 0.03501 = 0.04355 -0.00363 -0.00317 0.01033 PART 1 AFIX 23 H20A 2 0.478875 0.447356 0.605667 31.00000 -1.20000 H20B 2 0.516998 0.409531 0.631761 31.00000 -1.20000 AFIX 23 PART 2 H20C 2 0.504988 0.470901 0.592100 -31.00000 -1.20000 H20D 2 0.485287 0.410358 0.631452 -31.00000 -1.20000 AFIX 0 PART 0 C21 1 0.495241 0.501258 0.685627 11.00000 0.02311 0.03672 = 0.04169 0.00967 0.00063 0.01517 AFIX 23 H21A 2 0.467648 0.452492 0.698759 11.00000 -1.20000 H21B 2 0.462437 0.512032 0.667593 11.00000 -1.20000 AFIX 0 C22 1 0.530033 0.553795 0.726057 11.00000 0.03037 0.03515 = 0.04261 0.00967 0.00044 0.02214 AFIX 23 H22A 2 0.565435 0.600751 0.712972 11.00000 -1.20000 H22B 2 0.494001 0.559299 0.744407 11.00000 -1.20000 AFIX 0 C23 1 0.817486 0.443651 0.417630 11.00000 0.06594 0.05736 = 0.05453 0.00362 0.01129 0.04419 AFIX 13 H23 2 0.780320 0.413655 0.393453 11.00000 -1.20000 AFIX 0 PART 1 O5A 6 0.648676 0.497913 0.596290 21.00000 0.01082 0.02317 = 0.01441 0.00420 -0.00603 0.00546 C19A 1 0.578197 0.478310 0.577663 31.00000 0.02718 0.03509 = 0.03308 -0.00341 -0.00886 0.01423 AFIX 23 H19A 2 0.562972 0.439138 0.554075 31.00000 -1.20000 H19B 2 0.580318 0.519484 0.560809 31.00000 -1.20000 AFIX 0 PART 2 O5 6 0.636251 0.499063 0.584277 -21.00000 0.03152 0.06630 = 0.05532 -0.02534 -0.01423 0.02060 C19 1 0.578059 0.438755 0.596587 -31.00000 0.06856 0.03991 = 0.04160 -0.00496 0.00452 0.02144 AFIX 23 H19C 2 0.590483 0.412473 0.620151 -31.00000 -1.20000 H19D 2 0.557500 0.408475 0.567690 -31.00000 -1.20000 AFIX 0 HKLF 4 REM R-3_a.res in R-3 REM wR2 = 0.2797, GooF = S = 1.113, Restrained GooF = 1.113 for all data REM R1 = 0.1032 for 5530 Fo > 4sig(Fo) and 0.1106 for all 6249 data REM 323 parameters refined using 2 restraints END WGHT 0.0967 164.8186 REM Highest difference peak 1.205, deepest hole -1.822, 1-sigma level 0.128 Q1 1 0.8798 0.4483 0.4451 11.00000 0.05 1.21 Q2 1 0.8385 0.4957 0.3686 11.00000 0.05 0.93 Q3 1 0.8407 0.3854 0.4111 11.00000 0.05 0.66 Q4 1 0.8266 0.4875 0.4461 11.00000 0.05 0.57 Q5 1 0.6667 0.3333 0.5265 10.33333 0.05 0.56 Q6 1 0.8357 0.5113 0.4102 11.00000 0.05 0.53 Q7 1 0.8576 0.4719 0.4516 11.00000 0.05 0.48 Q8 1 0.8320 0.5240 0.6965 11.00000 0.05 0.46 Q9 1 0.6315 0.6121 0.7843 11.00000 0.05 0.46 Q10 1 0.5379 0.4730 0.6694 11.00000 0.05 0.45 ; _shelx_res_checksum 7816 _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 I1 I 0.666667 0.333333 0.333333 0.0764(4) Uani 1 6 d S T P . . Cl1 Cl 0.77585(15) 0.45201(16) 0.46828(10) 0.1070(9) Uani 1 1 d . . . . . Cl2 Cl 0.8657(2) 0.4040(2) 0.43102(15) 0.169(2) Uani 1 1 d . . . . . Cl3 Cl 0.87393(14) 0.52720(11) 0.39164(9) 0.0854(7) Uani 1 1 d . . . . . O1 O 0.56412(16) 0.52671(15) 0.75685(12) 0.0288(6) Uani 1 1 d . . . . . O2 O 0.64841(15) 0.48113(14) 0.79654(9) 0.0217(5) Uani 1 1 d . . . . . O3 O 0.79980(14) 0.49188(13) 0.69890(9) 0.0212(5) Uani 1 1 d . . . . . O4 O 0.78377(18) 0.53689(16) 0.61694(11) 0.0338(7) Uani 1 1 d . . . . . O6 O 0.54871(19) 0.5065(3) 0.65513(16) 0.0589(12) Uani 1 1 d . . . . . N1 N 0.6194(4) 0.3551(4) 0.6212(3) 0.0755(18) Uani 1 1 d . . . . . H1A H 0.573886 0.323876 0.618055 0.091 Uiso 0.9167 1 calc R U P . . H1B H 0.633556 0.400722 0.622766 0.091 Uiso 0.9167 1 calc R U P . . C00Y C 0.666667 0.333333 0.6236(4) 0.050(2) Uani 1 3 d S T P . . C1 C 0.6194(2) 0.5740(2) 0.78482(15) 0.0248(8) Uani 1 1 d . . . . . C2 C 0.6334(3) 0.6427(2) 0.79610(18) 0.0343(10) Uani 1 1 d . . . . . H2 H 0.602752 0.658802 0.784613 0.041 Uiso 1 1 calc R U . . . C3 C 0.6919(3) 0.6871(2) 0.82399(17) 0.0378(11) Uani 1 1 d . . . . . H3 H 0.700860 0.733384 0.831729 0.045 Uiso 1 1 calc R U . . . C4 C 0.7373(3) 0.6648(2) 0.84064(15) 0.0340(10) Uani 1 1 d . . . . . H4 H 0.777852 0.695952 0.859185 0.041 Uiso 1 1 calc R U . . . C5 C 0.7232(2) 0.5959(2) 0.82999(13) 0.0254(8) Uani 1 1 d . . . . . H5 H 0.754232 0.580187 0.841305 0.031 Uiso 1 1 calc R U . . . C6 C 0.6643(2) 0.55100(19) 0.80314(13) 0.0213(7) Uani 1 1 d . . . . . C7 C 0.6640(2) 0.46594(19) 0.74868(13) 0.0196(7) Uani 1 1 d . . . . . H7A H 0.710634 0.504957 0.737623 0.024 Uiso 1 1 calc R U . . . H7B H 0.627179 0.461305 0.725617 0.024 Uiso 1 1 calc R U . . . C8 C 0.66539(19) 0.39713(18) 0.75121(12) 0.0169(6) Uani 1 1 d . . . . . C9 C 0.73049(18) 0.39831(18) 0.75125(12) 0.0173(6) Uani 1 1 d . . . . . C10 C 0.79839(19) 0.46844(19) 0.74757(13) 0.0211(7) Uani 1 1 d . . . . . H10A H 0.798593 0.502971 0.770953 0.025 Uiso 1 1 calc R U . . . H10B H 0.839992 0.462585 0.753943 0.025 Uiso 1 1 calc R U . . . C11 C 0.85159(19) 0.55980(19) 0.68750(13) 0.0195(7) Uani 1 1 d . . . . . C12 C 0.9092(2) 0.6024(2) 0.71604(15) 0.0249(8) Uani 1 1 d . . . . . H12 H 0.914514 0.585852 0.746629 0.030 Uiso 1 1 calc R U . . . C13 C 0.9601(2) 0.6702(2) 0.69996(17) 0.0324(9) Uani 1 1 d . . . . . H13 H 1.000137 0.699547 0.719470 0.039 Uiso 1 1 calc R U . . . C14 C 0.9517(2) 0.6941(2) 0.65567(17) 0.0319(9) Uani 1 1 d . . . . . H14 H 0.986136 0.740138 0.644853 0.038 Uiso 1 1 calc R U . . . C15 C 0.8937(2) 0.6518(2) 0.62683(15) 0.0293(9) Uani 1 1 d . . . . . H15 H 0.888360 0.668717 0.596399 0.035 Uiso 1 1 calc R U . . . C16 C 0.8431(2) 0.5842(2) 0.64258(13) 0.0229(7) Uani 1 1 d . . . . . C17 C 0.7678(2) 0.5628(3) 0.57417(16) 0.0368(10) Uani 1 1 d . . . . . H17A H 0.803409 0.571544 0.548856 0.044 Uiso 1 1 calc R U . . . H17B H 0.768910 0.608032 0.580989 0.044 Uiso 1 1 calc R U . . . C18 C 0.6952(3) 0.5079(4) 0.55734(18) 0.0486(14) Uani 1 1 d D . . . . H18A H 0.681461 0.524644 0.528266 0.058 Uiso 0.46(9) 1 calc R U P A 1 H18B H 0.694044 0.462893 0.549489 0.058 Uiso 0.46(9) 1 calc R U P A 1 H18C H 0.689362 0.519700 0.523773 0.058 Uiso 0.54(9) 1 calc R U P A 2 H18D H 0.693544 0.461556 0.556413 0.058 Uiso 0.54(9) 1 calc R U P A 2 C20 C 0.5248(3) 0.4551(3) 0.61834(19) 0.0397(11) Uani 1 1 d D . . . . H20A H 0.478875 0.447356 0.605667 0.048 Uiso 0.579(18) 1 calc R U P B 1 H20B H 0.516998 0.409531 0.631761 0.048 Uiso 0.579(18) 1 calc R U P B 1 H20C H 0.504988 0.470901 0.592100 0.048 Uiso 0.421(18) 1 calc R U P B 2 H20D H 0.485287 0.410358 0.631452 0.048 Uiso 0.421(18) 1 calc R U P B 2 C21 C 0.4952(2) 0.5013(3) 0.68563(18) 0.0337(9) Uani 1 1 d . . . . . H21A H 0.467648 0.452492 0.698759 0.040 Uiso 1 1 calc R U . . . H21B H 0.462437 0.512032 0.667593 0.040 Uiso 1 1 calc R U . . . C22 C 0.5300(2) 0.5538(3) 0.72606(18) 0.0335(9) Uani 1 1 d . . . . . H22A H 0.565435 0.600751 0.712972 0.040 Uiso 1 1 calc R U . . . H22B H 0.494001 0.559299 0.744407 0.040 Uiso 1 1 calc R U . . . C23 C 0.8175(4) 0.4437(3) 0.4176(2) 0.0533(14) Uani 1 1 d . . . . . H23 H 0.780320 0.413655 0.393453 0.064 Uiso 1 1 calc R U . . . O5A O 0.6487(11) 0.4979(8) 0.5963(6) 0.017(4) Uani 0.46(9) 1 d D . P A 1 C19A C 0.5782(4) 0.4783(5) 0.5777(3) 0.032(2) Uani 0.579(18) 1 d D . P A 1 H19A H 0.562972 0.439138 0.554075 0.039 Uiso 0.579(18) 1 calc R U P B 1 H19B H 0.580318 0.519484 0.560809 0.039 Uiso 0.579(18) 1 calc R U P B 1 O5 O 0.6363(12) 0.4991(12) 0.5843(16) 0.053(5) Uani 0.54(9) 1 d D . P A 2 C19 C 0.5781(8) 0.4388(8) 0.5966(5) 0.053(5) Uani 0.421(18) 1 d D . P A 2 H19C H 0.590483 0.412473 0.620151 0.063 Uiso 0.421(18) 1 calc R U P B 2 H19D H 0.557500 0.408475 0.567690 0.063 Uiso 0.421(18) 1 calc R U P B 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 I1 0.0938(6) 0.0938(6) 0.0416(6) 0.000 0.000 0.0469(3) Cl1 0.1028(18) 0.124(2) 0.0967(17) -0.0120(15) 0.0467(14) 0.0583(16) Cl2 0.189(3) 0.230(4) 0.198(3) 0.160(3) 0.129(3) 0.187(3) Cl3 0.1202(18) 0.0628(11) 0.0914(15) 0.0171(10) 0.0373(13) 0.0594(12) O1 0.0280(14) 0.0231(14) 0.0395(17) 0.0043(12) -0.0026(12) 0.0158(12) O2 0.0326(14) 0.0168(12) 0.0195(12) 0.0027(9) 0.0051(10) 0.0153(11) O3 0.0210(12) 0.0148(12) 0.0199(12) 0.0027(9) -0.0005(10) 0.0030(10) O4 0.0416(18) 0.0268(15) 0.0272(15) -0.0005(12) -0.0115(13) 0.0128(14) O6 0.0246(17) 0.073(3) 0.058(3) -0.026(2) 0.0031(16) 0.0090(18) N1 0.064(4) 0.065(4) 0.103(5) 0.011(4) 0.011(3) 0.036(3) C00Y 0.051(3) 0.051(3) 0.049(5) 0.000 0.000 0.0255(17) C1 0.0289(19) 0.0213(17) 0.0271(19) 0.0033(14) 0.0063(15) 0.0146(15) C2 0.046(3) 0.027(2) 0.040(2) 0.0039(17) 0.009(2) 0.026(2) C3 0.057(3) 0.0218(19) 0.034(2) -0.0034(17) 0.009(2) 0.020(2) C4 0.045(3) 0.026(2) 0.0218(19) -0.0031(15) 0.0032(17) 0.0102(18) C5 0.033(2) 0.0254(18) 0.0158(16) 0.0003(13) 0.0018(14) 0.0132(16) C6 0.0300(19) 0.0177(16) 0.0172(16) 0.0015(12) 0.0055(13) 0.0125(15) C7 0.0240(17) 0.0186(16) 0.0200(16) 0.0012(13) 0.0010(13) 0.0135(14) C8 0.0199(16) 0.0148(15) 0.0174(15) -0.0005(11) -0.0020(12) 0.0098(13) C9 0.0154(15) 0.0178(16) 0.0164(15) 0.0000(12) -0.0021(12) 0.0067(13) C10 0.0186(16) 0.0177(16) 0.0200(16) 0.0027(13) -0.0019(13) 0.0039(13) C11 0.0177(16) 0.0162(16) 0.0221(17) 0.0020(13) 0.0051(13) 0.0068(13) C12 0.0207(17) 0.0244(18) 0.0267(19) 0.0058(14) -0.0013(14) 0.0090(15) C13 0.0193(18) 0.027(2) 0.041(2) 0.0058(17) -0.0005(16) 0.0041(16) C14 0.027(2) 0.0254(19) 0.040(2) 0.0129(17) 0.0100(17) 0.0100(16) C15 0.033(2) 0.030(2) 0.0244(19) 0.0095(15) 0.0068(16) 0.0152(18) C16 0.0279(19) 0.0244(18) 0.0188(17) 0.0008(13) 0.0020(14) 0.0147(16) C17 0.031(2) 0.056(3) 0.023(2) 0.0092(19) 0.0030(16) 0.021(2) C18 0.035(3) 0.079(4) 0.029(2) -0.005(2) -0.0070(19) 0.026(3) C20 0.032(2) 0.035(2) 0.044(3) -0.004(2) -0.0032(19) 0.010(2) C21 0.0231(19) 0.037(2) 0.042(2) 0.0097(19) 0.0006(17) 0.0152(18) C22 0.030(2) 0.035(2) 0.043(2) 0.0097(19) 0.0004(18) 0.0221(19) C23 0.066(4) 0.057(3) 0.055(3) 0.004(3) 0.011(3) 0.044(3) O5A 0.011(5) 0.023(6) 0.014(5) 0.004(3) -0.006(3) 0.005(4) C19A 0.027(4) 0.035(5) 0.033(4) -0.003(3) -0.009(3) 0.014(3) O5 0.032(5) 0.066(7) 0.055(10) -0.025(6) -0.014(7) 0.021(5) C19 0.069(10) 0.040(8) 0.042(7) -0.005(6) 0.005(6) 0.021(7) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' I I -0.4742 1.8119 '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 C1 O1 C22 117.9(3) . . ? C6 O2 C7 114.3(3) . . ? C11 O3 C10 117.3(3) . . ? C16 O4 C17 117.1(3) . . ? C21 O6 C20 114.4(4) . . ? H1A N1 H1B 120.0 . . ? C00Y N1 H1A 120.0 . . ? C00Y N1 H1B 120.0 . . ? N1 C00Y N1 119.76(10) 2_655 . ? N1 C00Y N1 119.76(10) 2_655 3_665 ? N1 C00Y N1 119.75(10) 3_665 . ? O1 C1 C2 124.7(4) . . ? O1 C1 C6 116.4(3) . . ? C6 C1 C2 118.8(4) . . ? C1 C2 H2 120.0 . . ? C3 C2 C1 120.1(4) . . ? C3 C2 H2 120.0 . . ? C2 C3 H3 119.6 . . ? C4 C3 C2 120.8(4) . . ? C4 C3 H3 119.6 . . ? C3 C4 H4 120.3 . . ? C3 C4 C5 119.4(4) . . ? C5 C4 H4 120.3 . . ? C4 C5 H5 120.0 . . ? C6 C5 C4 120.1(4) . . ? C6 C5 H5 120.0 . . ? O2 C6 C1 120.5(4) . . ? C5 C6 O2 118.7(3) . . ? C5 C6 C1 120.7(4) . . ? O2 C7 H7A 110.1 . . ? O2 C7 H7B 110.1 . . ? O2 C7 C8 107.8(3) . . ? H7A C7 H7B 108.5 . . ? C8 C7 H7A 110.1 . . ? C8 C7 H7B 110.1 . . ? C9 C8 C7 120.0(3) . . ? C9 C8 C7 120.0(3) 2_655 . ? C9 C8 C9 119.9(3) 2_655 . ? C8 C9 C8 120.1(3) 3_665 . ? C8 C9 C10 119.2(3) . . ? C8 C9 C10 120.6(3) 3_665 . ? O3 C10 C9 105.0(3) . . ? O3 C10 H10A 110.7 . . ? O3 C10 H10B 110.7 . . ? C9 C10 H10A 110.7 . . ? C9 C10 H10B 110.7 . . ? H10A C10 H10B 108.8 . . ? O3 C11 C12 124.9(3) . . ? O3 C11 C16 114.8(3) . . ? C12 C11 C16 120.3(3) . . ? C11 C12 H12 120.0 . . ? C11 C12 C13 119.9(4) . . ? C13 C12 H12 120.0 . . ? C12 C13 H13 120.1 . . ? C14 C13 C12 119.7(4) . . ? C14 C13 H13 120.1 . . ? C13 C14 H14 119.6 . . ? C13 C14 C15 120.7(4) . . ? C15 C14 H14 119.6 . . ? C14 C15 H15 120.1 . . ? C14 C15 C16 119.8(4) . . ? C16 C15 H15 120.1 . . ? O4 C16 C11 115.2(3) . . ? O4 C16 C15 125.2(4) . . ? C15 C16 C11 119.6(4) . . ? O4 C17 H17A 110.1 . . ? O4 C17 H17B 110.1 . . ? O4 C17 C18 108.1(4) . . ? H17A C17 H17B 108.4 . . ? C18 C17 H17A 110.1 . . ? C18 C17 H17B 110.1 . . ? C17 C18 H18A 110.6 . . ? C17 C18 H18B 110.6 . . ? C17 C18 H18C 107.9 . . ? C17 C18 H18D 107.9 . . ? H18A C18 H18B 108.7 . . ? H18C C18 H18D 107.2 . . ? O5A C18 C17 105.7(10) . . ? O5A C18 H18A 110.6 . . ? O5A C18 H18B 110.6 . . ? O5 C18 C17 117.8(13) . . ? O5 C18 H18C 107.9 . . ? O5 C18 H18D 107.9 . . ? O6 C20 H20A 109.4 . . ? O6 C20 H20B 109.4 . . ? O6 C20 H20C 108.0 . . ? O6 C20 H20D 108.0 . . ? O6 C20 C19A 111.0(5) . . ? O6 C20 C19 117.3(7) . . ? H20A C20 H20B 108.0 . . ? H20C C20 H20D 107.2 . . ? C19A C20 H20A 109.4 . . ? C19A C20 H20B 109.4 . . ? C19 C20 H20C 108.0 . . ? C19 C20 H20D 108.0 . . ? O6 C21 H21A 110.1 . . ? O6 C21 H21B 110.1 . . ? O6 C21 C22 107.9(4) . . ? H21A C21 H21B 108.4 . . ? C22 C21 H21A 110.1 . . ? C22 C21 H21B 110.1 . . ? O1 C22 C21 107.3(4) . . ? O1 C22 H22A 110.3 . . ? O1 C22 H22B 110.3 . . ? C21 C22 H22A 110.3 . . ? C21 C22 H22B 110.3 . . ? H22A C22 H22B 108.5 . . ? Cl1 C23 Cl3 110.8(4) . . ? Cl1 C23 H23 108.5 . . ? Cl2 C23 Cl1 111.4(4) . . ? Cl2 C23 Cl3 109.0(4) . . ? Cl2 C23 H23 108.5 . . ? Cl3 C23 H23 108.5 . . ? C18 O5A C19A 109.8(14) . . ? C20 C19A H19A 109.5 . . ? C20 C19A H19B 109.5 . . ? O5A C19A C20 110.6(7) . . ? O5A C19A H19A 109.5 . . ? O5A C19A H19B 109.5 . . ? H19A C19A H19B 108.1 . . ? C19 O5 C18 128.3(16) . . ? C20 C19 H19C 109.7 . . ? C20 C19 H19D 109.7 . . ? O5 C19 C20 109.6(13) . . ? O5 C19 H19C 109.7 . . ? O5 C19 H19D 109.7 . . ? H19C C19 H19D 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 Cl1 C23 1.728(6) . ? Cl2 C23 1.698(6) . ? Cl3 C23 1.759(7) . ? O1 C1 1.367(5) . ? O1 C22 1.435(5) . ? O2 C6 1.391(4) . ? O2 C7 1.448(4) . ? O3 C10 1.437(4) . ? O3 C11 1.373(4) . ? O4 C16 1.378(5) . ? O4 C17 1.428(5) . ? O6 C20 1.406(6) . ? O6 C21 1.395(6) . ? N1 H1A 0.8800 . ? N1 H1B 0.8800 . ? N1 C00Y 1.331(6) . ? C1 C2 1.401(6) . ? C1 C6 1.396(6) . ? C2 H2 0.9500 . ? C2 C3 1.385(7) . ? C3 H3 0.9500 . ? C3 C4 1.376(8) . ? C4 H4 0.9500 . ? C4 C5 1.402(6) . ? C5 H5 0.9500 . ? C5 C6 1.377(6) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C7 C8 1.512(5) . ? C8 C9 1.402(5) . ? C8 C9 1.398(5) 2_655 ? C9 C10 1.504(5) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.375(5) . ? C11 C16 1.402(5) . ? C12 H12 0.9500 . ? C12 C13 1.401(6) . ? C13 H13 0.9500 . ? C13 C14 1.380(6) . ? C14 H14 0.9500 . ? C14 C15 1.384(7) . ? C15 H15 0.9500 . ? C15 C16 1.393(6) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C17 C18 1.499(7) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C18 H18C 0.9900 . ? C18 H18D 0.9900 . ? C18 O5A 1.420(10) . ? C18 O5 1.411(12) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C20 H20C 0.9900 . ? C20 H20D 0.9900 . ? C20 C19A 1.512(9) . ? C20 C19 1.497(14) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C21 C22 1.506(7) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 H23 1.0000 . ? O5A C19A 1.46(2) . ? C19A H19A 0.9900 . ? C19A H19B 0.9900 . ? O5 C19 1.33(2) . ? C19 H19C 0.9900 . ? C19 H19D 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 C1 C2 C3 -178.6(4) . . . . ? O1 C1 C6 O2 -5.9(5) . . . . ? O1 C1 C6 C5 177.2(3) . . . . ? O2 C7 C8 C9 79.5(4) . . . 2_655 ? O2 C7 C8 C9 -103.5(4) . . . . ? O3 C11 C12 C13 177.9(4) . . . . ? O3 C11 C16 O4 0.7(5) . . . . ? O3 C11 C16 C15 -178.3(3) . . . . ? O4 C17 C18 O5A 58.3(8) . . . . ? O4 C17 C18 O5 72(2) . . . . ? O6 C20 C19A O5A 52.7(9) . . . . ? O6 C20 C19 O5 -50(3) . . . . ? O6 C21 C22 O1 -72.2(5) . . . . ? C1 O1 C22 C21 156.4(4) . . . . ? C1 C2 C3 C4 0.5(7) . . . . ? C2 C1 C6 O2 174.0(4) . . . . ? C2 C1 C6 C5 -3.0(6) . . . . ? C2 C3 C4 C5 -1.3(7) . . . . ? C3 C4 C5 C6 -0.1(6) . . . . ? C4 C5 C6 O2 -174.8(3) . . . . ? C4 C5 C6 C1 2.2(6) . . . . ? C6 O2 C7 C8 163.3(3) . . . . ? C6 C1 C2 C3 1.6(6) . . . . ? C7 O2 C6 C1 77.2(4) . . . . ? C7 O2 C6 C5 -105.9(4) . . . . ? C7 C8 C9 C8 -176.9(2) . . . 3_665 ? C7 C8 C9 C10 -1.4(5) . . . . ? C8 C9 C10 O3 -70.7(4) . . . . ? C8 C9 C10 O3 104.7(4) 3_665 . . . ? C9 C8 C9 C8 0.1(7) 2_655 . . 3_665 ? C9 C8 C9 C10 175.6(2) 2_655 . . . ? C10 O3 C11 C12 12.1(5) . . . . ? C10 O3 C11 C16 -169.2(3) . . . . ? C11 O3 C10 C9 171.1(3) . . . . ? C11 C12 C13 C14 0.6(7) . . . . ? C12 C11 C16 O4 179.5(4) . . . . ? C12 C11 C16 C15 0.5(6) . . . . ? C12 C13 C14 C15 -0.2(7) . . . . ? C13 C14 C15 C16 0.0(7) . . . . ? C14 C15 C16 O4 -179.0(4) . . . . ? C14 C15 C16 C11 -0.1(6) . . . . ? C16 O4 C17 C18 -169.6(4) . . . . ? C16 C11 C12 C13 -0.7(6) . . . . ? C17 O4 C16 C11 171.8(4) . . . . ? C17 O4 C16 C15 -9.3(6) . . . . ? C17 C18 O5A C19A 149.6(8) . . . . ? C17 C18 O5 C19 -138(4) . . . . ? C18 O5A C19A C20 170.2(7) . . . . ? C18 O5 C19 C20 -171(4) . . . . ? C20 O6 C21 C22 173.5(4) . . . . ? C21 O6 C20 C19A 160.2(5) . . . . ? C21 O6 C20 C19 -157.3(8) . . . . ? C22 O1 C1 C2 18.4(6) . . . . ? C22 O1 C1 C6 -161.8(4) . . . . ?