#------------------------------------------------------------------------------ #$Date: 2020-05-16 05:00:21 +0300 (Sat, 16 May 2020) $ #$Revision: 252073 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/05/7240540.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_7240540 loop_ _publ_author_name 'Oburn, Shalisa M.' 'Santana, Carlos' 'Elacqua, Elizabeth' 'Groeneman , Ryan' _publ_section_title ; A diamondoid net sustained by halogen bonds: employing a cyclobutane to generate a tetrahedral architecture ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/D0CE00627K _journal_year 2020 _chemical_formula_moiety '2(C6 Cl4 I2), C24 H20 N4, 2(C7 H8)' _chemical_formula_sum 'C50 H36 Cl8 I4 N4' _chemical_formula_weight 1484.03 _space_group_crystal_system orthorhombic _space_group_IT_number 41 _space_group_name_Hall 'A 2 -2ab' _space_group_name_H-M_alt 'A e a 2' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_date 2020-04-13 _audit_creation_method ; Olex2 1.3 (compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032) ; _audit_update_record ; 2020-04-20 deposited with the CCDC. 2020-05-14 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.0411(4) _cell_length_b 16.8624(7) _cell_length_c 28.2059(7) _cell_measurement_reflns_used 9616 _cell_measurement_temperature 100 _cell_measurement_theta_max 28.29 _cell_measurement_theta_min 2.32 _cell_volume 5251.4(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 'SHELXS-1997 (Sheldrick, 2008)' _diffrn_ambient_temperature 100 _diffrn_measured_fraction_theta_full 0.997 _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 0.0309 _diffrn_reflns_av_unetI/netI 0.0182 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_number 55382 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.996 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.287 _diffrn_reflns_theta_min 2.320 _exptl_absorpt_coefficient_mu 2.820 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.877 _exptl_crystal_description block _exptl_crystal_F_000 2848 _exptl_crystal_size_max 0.137 _exptl_crystal_size_mid 0.112 _exptl_crystal_size_min 0.107 _refine_diff_density_max 0.683 _refine_diff_density_min -0.582 _refine_diff_density_rms 0.053 _refine_ls_abs_structure_details ; Flack x determined using 3067 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.012(5) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 309 _refine_ls_number_reflns 6505 _refine_ls_number_restraints 133 _refine_ls_restrained_S_all 1.030 _refine_ls_R_factor_all 0.0144 _refine_ls_R_factor_gt 0.0140 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0118P)^2^+5.3941P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0319 _refine_ls_wR_factor_ref 0.0323 _reflns_Friedel_coverage 0.955 _reflns_Friedel_fraction_full 0.997 _reflns_Friedel_fraction_max 0.994 _reflns_number_gt 6413 _reflns_number_total 6505 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ce00627k2.cif _cod_data_source_block g23719 _cod_original_sg_symbol_Hall 'A 2 -2ac' _cod_database_code 7240540 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups 2. Uiso/Uaniso restraints and constraints C5A \\sim C4A \\sim C3A \\sim C2A \\sim C6A \\sim C1A \\sim C7A: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08 within 1.7A Uanis(C4A) = Uanis(C5A) = Uanis(C6A) = Uanis(C1A) = Uanis(C2A) = Uanis(C3A) 3. Rigid body (RIGU) restrains C6B, C3B, C2B, C7B, C1B, C4B, C5B with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004 C6A, C5A, C4A, C3A, C2A, C1A, C7A with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004 4. Others Fixed Sof: C2A(0.5) H2A(0.5) C1A(0.5) C6A(0.5) H6A(0.5) C5A(0.5) H5A(0.5) C4A(0.5) H4A(0.5) C3A(0.5) H3A(0.5) C7A(0.5) H7AA(0.5) H7AB(0.5) H7AC(0.5) C1B(0.5) H1B(0.5) C2B(0.5) C3B(0.5) H3B(0.5) C6B(0.5) H6B(0.5) C5B(0.5) H5B(0.5) C4B(0.5) H4B(0.5) C7B(0.5) H7BA(0.5) H7BB(0.5) H7BC(0.5) 5.a Ternary CH refined with riding coordinates: C12(H12), C6(H6) 5.b Aromatic/amide H refined with riding coordinates: C10(H10), C5(H5), C4(H4), C11(H11), C7(H7), C8(H8), C2(H2), C1(H1), C2A(H2A), C6A(H6A), C5A(H5A), C4A(H4A), C3A(H3A), C1B(H1B), C3B(H3B), C6B(H6B), C5B(H5B), C4B(H4B) 5.c Fitted hexagon refined as free rotating group: C2A(C1A,C6A,C5A,C4A,C3A), C1B(C2B,C3B,C6B,C5B,C4B) 5.d Idealised Me refined as rotating group: C7A(H7AA,H7AB,H7AC), C7B(H7BA,H7BB,H7BC) ; _shelx_res_file ; TITL g23719 in Aba2 g23719.res created by SHELXL-2018/3 at 01:42:40 on 20-Apr-2020 CELL 0.71073 11.0411 16.8624 28.2059 90 90 90 ZERR 4 0.0004 0.0007 0.0007 0 0 0 LATT -5 SYMM -X,-Y,+Z SYMM 0.5+X,0.5-Y,+Z SYMM 0.5-X,0.5+Y,+Z SFAC C H Cl I N UNIT 200 144 32 16 16 EQIV $1 2-X,2-Y,+Z RIGU C6B C3B C2B C7B C1B C4B C5B RIGU C6A C5A C4A C3A C2A C1A C7A SIMU 0.04 0.08 1.7 C5A C4A C3A C2A C6A C1A C7A EADP C4A C5A C6A C1A C2A C3A L.S. 4 PLAN 7 CONF FREE C5B C3B_$1 FREE C5B C2B_$1 FREE C1A C3A_$1 FREE C6A C3A_$1 FREE C6A C6A_$1 FREE C6A C4A_$1 FREE C2B C1B_$1 FREE C2B C2B_$1 FREE C3B C2B_$1 FREE C3B C3B_$1 FREE C6B C2B_$1 FREE C6B C6B_$1 FREE C6B C3B_$1 FREE C2A C1A_$1 FREE C4A C1A_$1 FREE C3A C2A_$1 FREE C5A C1A_$1 FREE C5A C5A_$1 FREE C7A C3A_$1 FREE C7A C4A_$1 FREE C1B C1B_$1 FREE C4B C2B_$1 FREE C7B C4B_$1 FREE C7B C5B_$1 BOND $H MORE -1 fmap 2 acta MERG 2 REM REM REM WGHT 0.011800 5.394101 FVAR 0.05153 I1 4 0.891358 0.609982 0.913579 11.00000 0.01971 0.01426 = 0.01896 0.00629 0.00129 0.00160 I2 4 0.738310 0.327615 1.086502 11.00000 0.02194 0.01501 = 0.01712 0.00457 -0.00077 -0.00408 CL3 3 0.719736 0.302039 0.968175 11.00000 0.03264 0.01420 = 0.02148 -0.00087 -0.00124 -0.00689 CL1 3 0.909855 0.633674 1.030929 11.00000 0.02678 0.01224 = 0.02324 0.00082 -0.00358 -0.00442 CL2 3 0.830094 0.513337 1.106116 11.00000 0.04269 0.01961 = 0.01479 0.00049 -0.00564 -0.00782 CL4 3 0.770362 0.429495 0.892899 11.00000 0.02833 0.02073 = 0.01475 0.00034 -0.00212 -0.00009 C13 1 0.843419 0.525189 0.964834 11.00000 0.01287 0.01480 = 0.01718 0.00402 0.00047 0.00147 N1 5 0.457640 0.764799 0.849607 11.00000 0.03745 0.01666 = 0.02643 -0.00828 0.00443 -0.00014 C14 1 0.856080 0.542389 1.012835 11.00000 0.01316 0.01155 = 0.02017 0.00133 -0.00079 -0.00035 C3 1 0.518027 0.613003 0.814740 11.00000 0.02346 0.01059 = 0.01083 -0.00003 0.00068 -0.00231 C15 1 0.822477 0.486856 1.047167 11.00000 0.01690 0.01462 = 0.01513 0.00037 -0.00159 -0.00024 C9 1 0.596861 0.588899 0.713550 11.00000 0.01930 0.01143 = 0.01202 -0.00113 0.00197 -0.00087 C18 1 0.797445 0.451190 0.951813 11.00000 0.01666 0.01697 = 0.01322 0.00108 -0.00038 0.00213 C12 1 0.563690 0.518390 0.743507 11.00000 0.01569 0.00944 = 0.01266 0.00025 0.00035 0.00093 AFIX 13 H12 2 0.622750 0.476171 0.737538 11.00000 -1.20000 AFIX 0 C16 1 0.781249 0.411456 1.034206 11.00000 0.01534 0.01395 = 0.01779 0.00486 -0.00098 -0.00184 C10 1 0.516964 0.627692 0.683273 11.00000 0.02022 0.01642 = 0.01648 0.00137 -0.00076 0.00013 AFIX 43 H10 2 0.436891 0.611102 0.680757 11.00000 -1.20000 AFIX 0 N2 5 0.671442 0.719213 0.659039 11.00000 0.03126 0.01981 = 0.02203 0.00621 0.00327 -0.00507 C17 1 0.769782 0.394183 0.986017 11.00000 0.01599 0.01306 = 0.01689 -0.00033 -0.00139 -0.00232 C5 1 0.386882 0.726772 0.818855 11.00000 0.03508 0.01960 = 0.02861 -0.00489 -0.00234 0.00928 AFIX 43 H5 2 0.316737 0.751923 0.808506 11.00000 -1.20000 AFIX 0 C4 1 0.412236 0.651656 0.801443 11.00000 0.03251 0.02039 = 0.02870 -0.01145 -0.01111 0.00757 AFIX 43 H4 2 0.358275 0.627107 0.780813 11.00000 -1.20000 AFIX 0 C11 1 0.558800 0.691687 0.656833 11.00000 0.02723 0.01702 = 0.02269 0.00542 0.00149 0.00191 AFIX 43 H11 2 0.504793 0.716681 0.636414 11.00000 -1.20000 AFIX 0 C7 1 0.747723 0.681921 0.688236 11.00000 0.02437 0.02635 = 0.02887 0.00762 -0.00091 -0.01086 AFIX 43 H7 2 0.827039 0.700215 0.690123 11.00000 -1.20000 AFIX 0 C8 1 0.715272 0.617815 0.715714 11.00000 0.02018 0.02438 = 0.02272 0.00610 -0.00232 -0.00442 AFIX 43 H8 2 0.771806 0.593960 0.735564 11.00000 -1.20000 AFIX 0 C2 1 0.591426 0.652983 0.846294 11.00000 0.03122 0.02443 = 0.04234 -0.01581 -0.01591 0.00501 AFIX 43 H2 2 0.663037 0.629878 0.856809 11.00000 -1.20000 AFIX 0 C1 1 0.558231 0.727877 0.862366 11.00000 0.04481 0.02633 = 0.05249 -0.02407 -0.01724 0.00415 AFIX 43 H1 2 0.609928 0.753585 0.883377 11.00000 -1.20000 AFIX 0 C6 1 0.553053 0.530812 0.798809 11.00000 0.01788 0.01268 = 0.01266 0.00141 -0.00240 0.00166 AFIX 13 H6 2 0.624456 0.510974 0.815699 11.00000 -1.20000 AFIX 66 PART -1 C2A 1 0.500726 0.507413 1.050523 10.50000 0.02432 0.07127 = 0.07577 -0.00927 -0.00248 0.01695 AFIX 43 H2A 2 0.506293 0.519119 1.082669 10.50000 -1.20000 AFIX 65 C1A 1 0.537053 0.563035 1.017047 10.50000 0.02432 0.07127 = 0.07577 -0.00927 -0.00248 0.01695 C6A 1 0.528732 0.545540 0.969000 10.50000 0.02432 0.07127 = 0.07577 -0.00927 -0.00248 0.01695 AFIX 43 H6A 2 0.553037 0.582755 0.946603 10.50000 -1.20000 AFIX 65 C5A 1 0.484083 0.472423 0.954427 10.50000 0.02432 0.07127 = 0.07577 -0.00927 -0.00248 0.01695 AFIX 43 H5A 2 0.478516 0.460718 0.922281 10.50000 -1.20000 AFIX 65 C4A 1 0.447756 0.416800 0.987902 10.50000 0.02432 0.07127 = 0.07577 -0.00927 -0.00248 0.01695 AFIX 43 H4A 2 0.417883 0.367880 0.978152 10.50000 -1.20000 AFIX 65 C3A 1 0.456076 0.434294 1.035950 10.50000 0.02432 0.07127 = 0.07577 -0.00927 -0.00248 0.01695 AFIX 43 H3A 2 0.431770 0.397079 1.058347 10.50000 -1.20000 AFIX 0 C7A 1 0.582845 0.638934 1.026379 10.50000 0.02022 0.05670 = 0.12674 0.00814 0.01243 0.01000 AFIX 137 H7AA 2 0.617043 0.640100 1.057664 10.50000 -1.50000 H7AB 2 0.518499 0.677065 1.024306 10.50000 -1.50000 H7AC 2 0.644371 0.651643 1.003562 10.50000 -1.50000 AFIX 66 C1B 1 1.006968 0.509012 0.781684 10.50000 0.04175 0.04836 = 0.01929 0.00212 -0.00440 0.00852 AFIX 43 H1B 2 1.024584 0.529309 0.811556 10.50000 -1.20000 AFIX 65 C2B 1 1.037203 0.551967 0.741323 10.50000 0.02721 0.03801 = 0.02963 0.00066 -0.00353 0.00816 C3B 1 1.010874 0.521630 0.696675 10.50000 0.04560 0.05406 = 0.01249 -0.00187 -0.00522 0.02133 AFIX 43 H3B 2 1.031103 0.550370 0.669671 10.50000 -1.20000 AFIX 65 C6B 1 0.954310 0.448337 0.692389 10.50000 0.05783 0.07728 = 0.04066 -0.02753 -0.00148 0.00324 AFIX 43 H6B 2 0.936694 0.428040 0.662516 10.50000 -1.20000 AFIX 65 C5B 1 0.924074 0.405381 0.732749 10.50000 0.04818 0.04649 = 0.06951 -0.02057 0.01382 -0.00732 AFIX 43 H5B 2 0.886229 0.356343 0.729881 10.50000 -1.20000 AFIX 65 C4B 1 0.950403 0.435717 0.777397 10.50000 0.05646 0.05082 = 0.04254 -0.00509 0.01582 0.00361 AFIX 43 H4B 2 0.930174 0.406976 0.804401 10.50000 -1.20000 AFIX 0 C7B 1 1.097100 0.631917 0.746011 10.50000 0.04282 0.04601 = 0.05856 -0.00063 0.00084 0.00060 AFIX 137 H7BA 2 1.036802 0.672812 0.744128 10.50000 -1.50000 H7BB 2 1.154790 0.638729 0.720874 10.50000 -1.50000 H7BC 2 1.137854 0.635124 0.776015 10.50000 -1.50000 AFIX 0 HKLF 4 REM g23719 in Aba2 REM wR2 = 0.0323, GooF = S = 1.038, Restrained GooF = 1.030 for all data REM R1 = 0.0140 for 6413 Fo > 4sig(Fo) and 0.0144 for all 6505 data REM 309 parameters refined using 133 restraints END WGHT 0.0118 5.3943 REM Highest difference peak 0.683, deepest hole -0.582, 1-sigma level 0.053 Q1 1 0.5000 0.5000 0.9723 10.50000 0.05 0.56 Q2 1 0.5372 0.5662 0.9678 11.00000 0.05 0.51 Q3 1 0.4593 0.4434 1.0585 11.00000 0.05 0.47 Q4 1 0.5299 0.5666 0.8112 11.00000 0.05 0.37 Q5 1 0.5000 0.5000 0.7965 10.50000 0.05 0.24 Q6 1 0.9651 0.5566 0.6605 11.00000 0.05 0.24 Q7 1 0.7815 0.4561 1.0420 11.00000 0.05 0.23 ; _shelx_res_checksum 66332 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/2, -y+1, z+1/2' '-x+1/2, y+1, z+1/2' 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 0.89136(2) 0.60998(2) 0.91358(2) 0.01765(4) Uani 1 1 d . . . . . I2 I 0.73831(2) 0.32762(2) 1.08650(2) 0.01802(4) Uani 1 1 d . . . . . Cl3 Cl 0.71974(7) 0.30204(4) 0.96817(3) 0.02277(15) Uani 1 1 d . . . . . Cl1 Cl 0.90985(7) 0.63367(4) 1.03093(3) 0.02075(14) Uani 1 1 d . . . . . Cl2 Cl 0.83009(8) 0.51334(4) 1.10612(3) 0.02570(16) Uani 1 1 d . . . . . Cl4 Cl 0.77036(7) 0.42950(4) 0.89290(3) 0.02127(14) Uani 1 1 d . . . . . C13 C 0.8434(2) 0.52519(16) 0.96483(10) 0.0149(5) Uani 1 1 d . . . . . N1 N 0.4576(3) 0.76480(16) 0.84961(10) 0.0268(6) Uani 1 1 d . . . . . C14 C 0.8561(2) 0.54239(16) 1.01284(10) 0.0150(5) Uani 1 1 d . . . . . C3 C 0.5180(3) 0.61300(16) 0.81474(10) 0.0150(5) Uani 1 1 d . . . . . C15 C 0.8225(3) 0.48686(16) 1.04717(10) 0.0155(5) Uani 1 1 d . . . . . C9 C 0.5969(3) 0.58890(16) 0.71355(10) 0.0142(5) Uani 1 1 d . . . . . C18 C 0.7974(3) 0.45119(17) 0.95181(10) 0.0156(5) Uani 1 1 d . . . . . C12 C 0.5637(2) 0.51839(15) 0.74351(9) 0.0126(5) Uani 1 1 d . . . . . H12 H 0.622750 0.476171 0.737538 0.015 Uiso 1 1 calc R U . . . C16 C 0.7812(3) 0.41146(17) 1.03421(10) 0.0157(5) Uani 1 1 d . . . . . C10 C 0.5170(3) 0.62769(17) 0.68327(10) 0.0177(6) Uani 1 1 d . . . . . H10 H 0.436891 0.611102 0.680757 0.021 Uiso 1 1 calc R U . . . N2 N 0.6714(3) 0.71921(17) 0.65904(10) 0.0244(6) Uani 1 1 d . . . . . C17 C 0.7698(3) 0.39418(16) 0.98602(11) 0.0153(5) Uani 1 1 d . . . . . C5 C 0.3869(3) 0.7268(2) 0.81886(13) 0.0278(7) Uani 1 1 d . . . . . H5 H 0.316737 0.751923 0.808506 0.033 Uiso 1 1 calc R U . . . C4 C 0.4122(3) 0.6517(2) 0.80144(12) 0.0272(7) Uani 1 1 d . . . . . H4 H 0.358275 0.627107 0.780813 0.033 Uiso 1 1 calc R U . . . C11 C 0.5588(3) 0.69169(19) 0.65683(12) 0.0223(6) Uani 1 1 d . . . . . H11 H 0.504793 0.716681 0.636414 0.027 Uiso 1 1 calc R U . . . C7 C 0.7477(3) 0.6819(2) 0.68824(13) 0.0265(7) Uani 1 1 d . . . . . H7 H 0.827039 0.700215 0.690123 0.032 Uiso 1 1 calc R U . . . C8 C 0.7153(3) 0.61782(19) 0.71571(11) 0.0224(6) Uani 1 1 d . . . . . H8 H 0.771806 0.593960 0.735564 0.027 Uiso 1 1 calc R U . . . C2 C 0.5914(3) 0.6530(2) 0.84629(14) 0.0327(8) Uani 1 1 d . . . . . H2 H 0.663037 0.629878 0.856809 0.039 Uiso 1 1 calc R U . . . C1 C 0.5582(4) 0.7279(2) 0.86237(16) 0.0412(10) Uani 1 1 d . . . . . H1 H 0.609928 0.753585 0.883377 0.049 Uiso 1 1 calc R U . . . C6 C 0.5531(3) 0.53081(16) 0.79881(10) 0.0144(5) Uani 1 1 d . . . . . H6 H 0.624456 0.510974 0.815699 0.017 Uiso 1 1 calc R U . . . C2A C 0.5007(9) 0.5074(5) 1.05052(18) 0.0571(11) Uani 0.5 1 d G U P A -1 H2A H 0.506293 0.519119 1.082669 0.069 Uiso 0.5 1 calc R U P A -1 C1A C 0.5371(7) 0.5630(4) 1.0170(2) 0.0571(11) Uani 0.5 1 d G U P A -1 C6A C 0.5287(7) 0.5455(4) 0.9690(2) 0.0571(11) Uani 0.5 1 d G U P A -1 H6A H 0.553037 0.582755 0.946603 0.069 Uiso 0.5 1 calc R U P A -1 C5A C 0.4841(7) 0.4724(4) 0.95443(18) 0.0571(11) Uani 0.5 1 d G U P A -1 H5A H 0.478516 0.460718 0.922281 0.069 Uiso 0.5 1 calc R U P A -1 C4A C 0.4478(5) 0.4168(4) 0.9879(2) 0.0571(11) Uani 0.5 1 d G U P A -1 H4A H 0.417883 0.367880 0.978152 0.069 Uiso 0.5 1 calc R U P A -1 C3A C 0.4561(7) 0.4343(4) 1.0359(2) 0.0571(11) Uani 0.5 1 d G U P A -1 H3A H 0.431770 0.397079 1.058347 0.069 Uiso 0.5 1 calc R U P A -1 C7A C 0.5828(8) 0.6389(6) 1.0264(5) 0.068(3) Uani 0.5 1 d . U P A -1 H7AA H 0.617043 0.640100 1.057664 0.102 Uiso 0.5 1 calc R U P A -1 H7AB H 0.518499 0.677065 1.024306 0.102 Uiso 0.5 1 calc R U P A -1 H7AC H 0.644371 0.651643 1.003562 0.102 Uiso 0.5 1 calc R U P A -1 C1B C 1.0070(8) 0.5090(4) 0.78168(12) 0.0365(17) Uani 0.5 1 d G . P B -1 H1B H 1.024584 0.529309 0.811556 0.044 Uiso 0.5 1 calc R U P B -1 C2B C 1.0372(5) 0.5520(3) 0.74132(17) 0.0316(15) Uani 0.5 1 d G . P B -1 C3B C 1.0109(7) 0.5216(4) 0.69668(13) 0.037(3) Uani 0.5 1 d G . P B -1 H3B H 1.031103 0.550370 0.669671 0.045 Uiso 0.5 1 calc R U P B -1 C6B C 0.9543(9) 0.4483(5) 0.69239(17) 0.059(4) Uani 0.5 1 d G . P B -1 H6B H 0.936694 0.428040 0.662516 0.070 Uiso 0.5 1 calc R U P B -1 C5B C 0.9241(7) 0.4054(3) 0.7327(2) 0.055(3) Uani 0.5 1 d G . P B -1 H5B H 0.886229 0.356343 0.729881 0.066 Uiso 0.5 1 calc R U P B -1 C4B C 0.9504(7) 0.4357(4) 0.77740(18) 0.050(2) Uani 0.5 1 d G . P B -1 H4B H 0.930174 0.406976 0.804401 0.060 Uiso 0.5 1 calc R U P B -1 C7B C 1.0971(9) 0.6319(6) 0.7460(4) 0.049(2) Uani 0.5 1 d . . P B -1 H7BA H 1.036802 0.672812 0.744128 0.074 Uiso 0.5 1 calc R U P B -1 H7BB H 1.154790 0.638729 0.720874 0.074 Uiso 0.5 1 calc R U P B -1 H7BC H 1.137854 0.635124 0.776015 0.074 Uiso 0.5 1 calc R U P B -1 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 0.01971(8) 0.01426(7) 0.01896(8) 0.00629(7) 0.00129(8) 0.00160(6) I2 0.02194(8) 0.01501(8) 0.01712(8) 0.00457(7) -0.00077(8) -0.00408(6) Cl3 0.0326(4) 0.0142(3) 0.0215(4) -0.0009(3) -0.0012(3) -0.0069(3) Cl1 0.0268(4) 0.0122(3) 0.0232(4) 0.0008(3) -0.0036(3) -0.0044(3) Cl2 0.0427(4) 0.0196(3) 0.0148(3) 0.0005(3) -0.0056(3) -0.0078(3) Cl4 0.0283(4) 0.0207(3) 0.0148(3) 0.0003(3) -0.0021(3) -0.0001(3) C13 0.0129(12) 0.0148(13) 0.0172(13) 0.0040(10) 0.0005(10) 0.0015(10) N1 0.0374(16) 0.0167(12) 0.0264(15) -0.0083(10) 0.0044(12) -0.0001(11) C14 0.0132(12) 0.0115(12) 0.0202(14) 0.0013(10) -0.0008(11) -0.0003(10) C3 0.0235(14) 0.0106(12) 0.0108(12) 0.0000(9) 0.0007(11) -0.0023(10) C15 0.0169(13) 0.0146(13) 0.0151(13) 0.0004(10) -0.0016(10) -0.0002(10) C9 0.0193(13) 0.0114(12) 0.0120(12) -0.0011(10) 0.0020(10) -0.0009(10) C18 0.0167(13) 0.0170(13) 0.0132(13) 0.0011(10) -0.0004(10) 0.0021(11) C12 0.0157(12) 0.0094(11) 0.0127(12) 0.0002(9) 0.0004(10) 0.0009(9) C16 0.0153(12) 0.0139(13) 0.0178(14) 0.0049(10) -0.0010(10) -0.0018(10) C10 0.0202(14) 0.0164(13) 0.0165(14) 0.0014(11) -0.0008(11) 0.0001(11) N2 0.0313(14) 0.0198(13) 0.0220(14) 0.0062(10) 0.0033(11) -0.0051(11) C17 0.0160(13) 0.0131(13) 0.0169(14) -0.0003(11) -0.0014(10) -0.0023(10) C5 0.0351(18) 0.0196(15) 0.0286(17) -0.0049(13) -0.0023(14) 0.0093(13) C4 0.0325(17) 0.0204(15) 0.0287(17) -0.0115(13) -0.0111(14) 0.0076(13) C11 0.0272(16) 0.0170(14) 0.0227(15) 0.0054(12) 0.0015(13) 0.0019(12) C7 0.0244(16) 0.0264(17) 0.0289(18) 0.0076(13) -0.0009(13) -0.0109(13) C8 0.0202(14) 0.0244(16) 0.0227(16) 0.0061(12) -0.0023(12) -0.0044(12) C2 0.0312(17) 0.0244(16) 0.042(2) -0.0158(15) -0.0159(15) 0.0050(14) C1 0.045(2) 0.0263(18) 0.052(3) -0.0241(17) -0.0172(19) 0.0042(16) C6 0.0179(13) 0.0127(12) 0.0127(13) 0.0014(10) -0.0024(10) 0.0017(11) C2A 0.0243(14) 0.071(3) 0.076(3) -0.009(2) -0.0025(19) 0.0169(15) C1A 0.0243(14) 0.071(3) 0.076(3) -0.009(2) -0.0025(19) 0.0169(15) C6A 0.0243(14) 0.071(3) 0.076(3) -0.009(2) -0.0025(19) 0.0169(15) C5A 0.0243(14) 0.071(3) 0.076(3) -0.009(2) -0.0025(19) 0.0169(15) C4A 0.0243(14) 0.071(3) 0.076(3) -0.009(2) -0.0025(19) 0.0169(15) C3A 0.0243(14) 0.071(3) 0.076(3) -0.009(2) -0.0025(19) 0.0169(15) C7A 0.020(4) 0.057(5) 0.127(10) 0.008(6) 0.012(5) 0.010(4) C1B 0.042(4) 0.048(5) 0.019(2) 0.002(4) -0.004(5) 0.009(3) C2B 0.027(4) 0.038(4) 0.030(4) 0.001(3) -0.004(3) 0.008(3) C3B 0.046(6) 0.054(8) 0.012(3) -0.002(3) -0.005(4) 0.021(6) C6B 0.058(8) 0.077(9) 0.041(5) -0.028(5) -0.001(5) 0.003(6) C5B 0.048(6) 0.046(6) 0.070(7) -0.021(5) 0.014(5) -0.007(5) C4B 0.056(6) 0.051(5) 0.043(5) -0.005(4) 0.016(4) 0.004(4) C7B 0.043(5) 0.046(5) 0.059(6) -0.001(5) 0.001(4) 0.001(4) 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' 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 C14 C13 I1 120.2(2) . . ? C14 C13 C18 118.6(3) . . ? C18 C13 I1 121.2(2) . . ? C1 N1 C5 116.3(3) . . ? C13 C14 Cl1 120.5(2) . . ? C13 C14 C15 120.5(3) . . ? C15 C14 Cl1 118.9(2) . . ? C4 C3 C6 124.5(3) . . ? C2 C3 C4 116.0(3) . . ? C2 C3 C6 119.4(3) . . ? C14 C15 Cl2 118.8(2) . . ? C14 C15 C16 121.0(3) . . ? C16 C15 Cl2 120.2(2) . . ? C10 C9 C12 124.2(3) . . ? C10 C9 C8 117.1(3) . . ? C8 C9 C12 118.6(3) . . ? C13 C18 Cl4 120.3(2) . . ? C17 C18 Cl4 118.8(2) . . ? C17 C18 C13 120.9(3) . . ? C9 C12 C12 122.8(2) . 2_665 ? C9 C12 H12 108.4 . . ? C9 C12 C6 117.9(2) . . ? C12 C12 H12 108.4 2_665 . ? C12 C12 C6 89.17(14) 2_665 . ? C6 C12 H12 108.4 . . ? C15 C16 I2 120.2(2) . . ? C17 C16 I2 121.6(2) . . ? C17 C16 C15 118.3(3) . . ? C9 C10 H10 120.5 . . ? C11 C10 C9 118.9(3) . . ? C11 C10 H10 120.5 . . ? C11 N2 C7 117.0(3) . . ? C18 C17 Cl3 119.3(2) . . ? C16 C17 Cl3 120.1(2) . . ? C16 C17 C18 120.6(3) . . ? N1 C5 H5 118.3 . . ? N1 C5 C4 123.5(3) . . ? C4 C5 H5 118.3 . . ? C3 C4 H4 119.9 . . ? C5 C4 C3 120.2(3) . . ? C5 C4 H4 119.9 . . ? C10 C11 H11 118.1 . . ? N2 C11 C10 123.8(3) . . ? N2 C11 H11 118.1 . . ? N2 C7 H7 118.2 . . ? N2 C7 C8 123.5(3) . . ? C8 C7 H7 118.2 . . ? C9 C8 H8 120.2 . . ? C7 C8 C9 119.5(3) . . ? C7 C8 H8 120.2 . . ? C3 C2 H2 120.0 . . ? C3 C2 C1 119.9(3) . . ? C1 C2 H2 120.0 . . ? N1 C1 C2 124.0(3) . . ? N1 C1 H1 118.0 . . ? C2 C1 H1 118.0 . . ? C3 C6 C12 115.8(2) . . ? C3 C6 C6 114.7(3) . 2_665 ? C3 C6 H6 112.0 . . ? C12 C6 H6 112.0 . . ? C6 C6 C12 88.15(14) 2_665 . ? C6 C6 H6 112.0 2_665 . ? C1A C2A H2A 120.0 . . ? C1A C2A C3A 120.0 . . ? C3A C2A H2A 120.0 . . ? C2A C1A C7A 126.4(8) . . ? C6A C1A C2A 120.0 . . ? C6A C1A C7A 113.6(8) . . ? C1A C6A H6A 120.0 . . ? C1A C6A C5A 120.0 . . ? C5A C6A H6A 120.0 . . ? C6A C5A H5A 120.0 . . ? C6A C5A C4A 120.0 . . ? C4A C5A H5A 120.0 . . ? C5A C4A H4A 120.0 . . ? C3A C4A C5A 120.0 . . ? C3A C4A H4A 120.0 . . ? C2A C3A H3A 120.0 . . ? C4A C3A C2A 120.0 . . ? C4A C3A H3A 120.0 . . ? C1A C7A H7AA 109.5 . . ? C1A C7A H7AB 109.5 . . ? C1A C7A H7AC 109.5 . . ? H7AA C7A H7AB 109.5 . . ? H7AA C7A H7AC 109.5 . . ? H7AB C7A H7AC 109.5 . . ? C2B C1B H1B 120.0 . . ? C2B C1B C4B 120.0 . . ? C4B C1B H1B 120.0 . . ? C1B C2B C7B 120.0(5) . . ? C3B C2B C1B 120.0 . . ? C3B C2B C7B 120.0(5) . . ? C2B C3B H3B 120.0 . . ? C2B C3B C6B 120.0 . . ? C6B C3B H3B 120.0 . . ? C3B C6B H6B 120.0 . . ? C5B C6B C3B 120.0 . . ? C5B C6B H6B 120.0 . . ? C6B C5B H5B 120.0 . . ? C6B C5B C4B 120.0 . . ? C4B C5B H5B 120.0 . . ? C1B C4B H4B 120.0 . . ? C5B C4B C1B 120.0 . . ? C5B C4B H4B 120.0 . . ? C2B C7B H7BA 109.5 . . ? C2B C7B H7BB 109.5 . . ? C2B C7B H7BC 109.5 . . ? H7BA C7B H7BB 109.5 . . ? H7BA C7B H7BC 109.5 . . ? H7BB C7B H7BC 109.5 . . ? 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 I1 C13 2.101(3) . ? I2 C16 2.097(3) . ? Cl3 C17 1.724(3) . ? Cl1 C14 1.727(3) . ? Cl2 C15 1.724(3) . ? Cl4 C18 1.728(3) . ? C13 C14 1.392(4) . ? C13 C18 1.396(4) . ? N1 C5 1.332(4) . ? N1 C1 1.323(5) . ? C14 C15 1.397(4) . ? C3 C4 1.389(4) . ? C3 C2 1.380(4) . ? C3 C6 1.507(4) . ? C15 C16 1.399(4) . ? C9 C12 1.504(4) . ? C9 C10 1.391(4) . ? C9 C8 1.397(4) . ? C18 C17 1.396(4) . ? C12 C12 1.537(5) 2_665 ? C12 H12 0.9800 . ? C12 C6 1.578(4) . ? C16 C17 1.396(4) . ? C10 H10 0.9300 . ? C10 C11 1.391(4) . ? N2 C11 1.329(4) . ? N2 C7 1.335(4) . ? C5 H5 0.9300 . ? C5 C4 1.387(4) . ? C4 H4 0.9300 . ? C11 H11 0.9300 . ? C7 H7 0.9300 . ? C7 C8 1.378(4) . ? C8 H8 0.9300 . ? C2 H2 0.9300 . ? C2 C1 1.391(5) . ? C1 H1 0.9300 . ? C6 C6 1.566(6) 2_665 ? C6 H6 0.9800 . ? C2A H2A 0.9300 . ? C2A C1A 1.3900 . ? C2A C3A 1.3900 . ? C1A C6A 1.3900 . ? C1A C7A 1.401(13) . ? C6A H6A 0.9300 . ? C6A C5A 1.3900 . ? C5A H5A 0.9300 . ? C5A C4A 1.3900 . ? C4A H4A 0.9300 . ? C4A C3A 1.3900 . ? C3A H3A 0.9300 . ? C7A H7AA 0.9600 . ? C7A H7AB 0.9600 . ? C7A H7AC 0.9600 . ? C1B H1B 0.9300 . ? C1B C2B 1.3900 . ? C1B C4B 1.3900 . ? C2B C3B 1.3900 . ? C2B C7B 1.507(11) . ? C3B H3B 0.9300 . ? C3B C6B 1.3900 . ? C6B H6B 0.9300 . ? C6B C5B 1.3900 . ? C5B H5B 0.9300 . ? C5B C4B 1.3900 . ? C4B H4B 0.9300 . ? C7B H7BA 0.9600 . ? C7B H7BB 0.9600 . ? C7B H7BC 0.9600 . ? 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 I1 C13 C14 Cl1 0.6(3) . . . . ? I1 C13 C14 C15 178.9(2) . . . . ? I1 C13 C18 Cl4 -3.8(3) . . . . ? I1 C13 C18 C17 177.8(2) . . . . ? I2 C16 C17 Cl3 -0.2(3) . . . . ? I2 C16 C17 C18 179.2(2) . . . . ? Cl1 C14 C15 Cl2 2.7(3) . . . . ? Cl1 C14 C15 C16 -178.4(2) . . . . ? Cl2 C15 C16 I2 -3.7(3) . . . . ? Cl2 C15 C16 C17 176.3(2) . . . . ? Cl4 C18 C17 Cl3 4.5(3) . . . . ? Cl4 C18 C17 C16 -174.9(2) . . . . ? C13 C14 C15 Cl2 -175.6(2) . . . . ? C13 C14 C15 C16 3.3(4) . . . . ? C13 C18 C17 Cl3 -177.1(2) . . . . ? C13 C18 C17 C16 3.5(4) . . . . ? N1 C5 C4 C3 -2.1(6) . . . . ? C14 C13 C18 Cl4 175.6(2) . . . . ? C14 C13 C18 C17 -2.8(4) . . . . ? C14 C15 C16 I2 177.4(2) . . . . ? C14 C15 C16 C17 -2.6(4) . . . . ? C3 C2 C1 N1 0.6(7) . . . . ? C15 C16 C17 Cl3 179.8(2) . . . . ? C15 C16 C17 C18 -0.8(4) . . . . ? C9 C12 C6 C3 28.2(3) . . . . ? C9 C12 C6 C6 144.8(3) . . . 2_665 ? C9 C10 C11 N2 -0.8(5) . . . . ? C18 C13 C14 Cl1 -178.8(2) . . . . ? C18 C13 C14 C15 -0.5(4) . . . . ? C12 C9 C10 C11 -179.1(3) . . . . ? C12 C9 C8 C7 179.4(3) . . . . ? C12 C12 C6 C3 -99.1(3) 2_665 . . . ? C12 C12 C6 C6 17.6(3) 2_665 . . 2_665 ? C10 C9 C12 C12 0.1(4) . . . 2_665 ? C10 C9 C12 C6 -108.7(3) . . . . ? C10 C9 C8 C7 -0.3(5) . . . . ? N2 C7 C8 C9 0.1(5) . . . . ? C5 N1 C1 C2 -1.1(6) . . . . ? C4 C3 C2 C1 -0.8(6) . . . . ? C4 C3 C6 C12 58.4(4) . . . . ? C4 C3 C6 C6 -42.2(3) . . . 2_665 ? C11 N2 C7 C8 -0.3(5) . . . . ? C7 N2 C11 C10 0.7(5) . . . . ? C8 C9 C12 C12 -179.6(3) . . . 2_665 ? C8 C9 C12 C6 71.6(3) . . . . ? C8 C9 C10 C11 0.6(4) . . . . ? C2 C3 C4 C5 1.5(5) . . . . ? C2 C3 C6 C12 -124.6(3) . . . . ? C2 C3 C6 C6 134.9(3) . . . 2_665 ? C1 N1 C5 C4 1.9(6) . . . . ? C6 C3 C4 C5 178.6(3) . . . . ? C6 C3 C2 C1 -178.1(4) . . . . ? C2A C1A C6A C5A 0.0 . . . . ? C1A C2A C3A C4A 0.0 . . . . ? C1A C6A C5A C4A 0.0 . . . . ? C6A C5A C4A C3A 0.0 . . . . ? C5A C4A C3A C2A 0.0 . . . . ? C3A C2A C1A C6A 0.0 . . . . ? C3A C2A C1A C7A 179.6(7) . . . . ? C7A C1A C6A C5A -179.6(6) . . . . ? C1B C2B C3B C6B 0.0 . . . . ? C2B C1B C4B C5B 0.0 . . . . ? C2B C3B C6B C5B 0.0 . . . . ? C3B C6B C5B C4B 0.0 . . . . ? C6B C5B C4B C1B 0.0 . . . . ? C4B C1B C2B C3B 0.0 . . . . ? C4B C1B C2B C7B 179.2(7) . . . . ? C7B C2B C3B C6B -179.2(7) . . . . ?