#------------------------------------------------------------------------------ #$Date: 2024-12-06 19:29:44 +0200 (Fri, 06 Dec 2024) $ #$Revision: 296459 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/93/7249382.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_7249382 loop_ _publ_author_name 'Jeon, Ie-Rang' 'Jeannin, Olivier' 'Robert, Antoine' 'Barri\`ere, Fr\'ed\'eric' 'Fourmigu\'e, Marc' _publ_section_title ; N-Iodophthalimide as a halogen bond donor, a comparison with N-iodosuccinimide and N-iodosaccharin ; _journal_issue 42 _journal_name_full CrystEngComm _journal_page_first 6075 _journal_page_last 6081 _journal_paper_doi 10.1039/D4CE00654B _journal_volume 26 _journal_year 2024 _chemical_formula_moiety 'C26 H16 I2 N4 O4' _chemical_formula_sum 'C26 H16 I2 N4 O4' _chemical_formula_weight 702.23 _chemical_name_common beta-(NIPht)2(p-bipy) _chemical_name_systematic 'Bis(N(iodophtalimide)(4,4'-bipyridine), beta phase' _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _symmetry_cell_setting monoclinic _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary 'dual - dual-space method e.g. SHELXD' _atom_sites_solution_secondary 'dual - dual-space method e.g. SHELXD' _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4.3 _audit_creation_date 2019-10-24T09:52:25-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_update_record ; 2024-06-27 deposited with the CCDC. 2024-09-25 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 97.896(3) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 7.5392(8) _cell_length_b 9.4310(10) _cell_length_c 17.2253(18) _cell_measurement_reflns_used 4213 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 26.46 _cell_measurement_theta_min 2.47 _cell_measurement_wavelength 0.71073 _cell_volume 1213.1(2) _computing_cell_refinement 'SAINT V8.34A integration software' _computing_data_collection 'Bruker APEX2 software' _computing_data_reduction 'SORTAV (Blessing, 1995)' _computing_molecular_graphics 'Ortep for Windows (Farrugia, 2012)' _computing_publication_material 'WinGX publication routines (Farrugia, 2012)' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXT-2014 (Sheldrick, 2014)' _diffrn_ambient_temperature 296(2) _diffrn_detector 'APEX-II CCD' _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.984 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Bruker APEX-II' _diffrn_measurement_method '\f or \w oscillation scans' _diffrn_orient_matrix_UB_11 2 _diffrn_orient_matrix_UB_12 -0.132804 _diffrn_orient_matrix_UB_13 -0.012704 _diffrn_orient_matrix_UB_21 2 _diffrn_orient_matrix_UB_22 0.008357 _diffrn_orient_matrix_UB_23 -0.014615 _diffrn_orient_matrix_UB_31 2 _diffrn_orient_matrix_UB_32 -0.014997 _diffrn_orient_matrix_UB_33 0.104249 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.048 _diffrn_reflns_av_unetI/netI 0.0386 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.984 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 2727 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.984 _diffrn_reflns_reduction_process ; Scaled and merged with Sortav R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397 ; _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.489 _diffrn_reflns_theta_min 2.387 _diffrn_source 'sealed x-ray tube' _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 2.634 _exptl_absorpt_correction_T_max 0.924 _exptl_absorpt_correction_T_min 0.768 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; TWINABS - Bruker AXS scaling for twinned crystals - Version 2012/1 ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.922 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 676 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CH2Cl2/pentane' _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.03 _refine_diff_density_max 0.668 _refine_diff_density_min -0.637 _refine_diff_density_rms 0.134 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.188 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_constraints 0 _refine_ls_number_parameters 164 _refine_ls_number_reflns 2727 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.188 _refine_ls_R_factor_all 0.0563 _refine_ls_R_factor_gt 0.0374 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0229P)^2^+1.7040P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0726 _refine_ls_wR_factor_ref 0.0788 _reflns_Friedel_coverage 0 _reflns_number_gt 2216 _reflns_number_total 2727 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4ce00654b1.cif _cod_data_source_block shelx_CCDC5 _cod_depositor_comments 'Adding full bibliography for 7249377--7249386.cif.' _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7249382 _shelx_res_file ; shelx.res created by SHELXL-2014/7 TITL shelxt_a.res in P2(1)/c CELL 0.71073 7.5392 9.4310 17.2253 90.000 97.896 90.000 ZERR 2.00 0.0008 0.0010 0.0018 0.000 0.003 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H I N O UNIT 52 32 4 8 8 MERG 0 FMAP 2 PLAN 20 BOND $H ACTA omit 1 0 0 omit -2 2 7 LIST 4 L.S. 10 TEMP 23.00 WGHT 0.022900 1.704000 BASF 0.41076 FVAR 0.43999 C1 1 0.174320 0.399811 0.560116 11.00000 0.03734 0.03316 = 0.03222 0.00228 0.00959 0.00636 C2 1 0.106815 0.271042 0.531620 11.00000 0.02693 0.03158 = 0.03669 0.00054 0.00316 0.00398 C3 1 0.025510 0.178250 0.577541 11.00000 0.03418 0.04326 = 0.04764 0.01352 0.00805 -0.00391 AFIX 43 H3 2 -0.019725 0.091446 0.558339 11.00000 -1.20000 AFIX 0 C4 1 0.014592 0.220590 0.653416 11.00000 0.04868 0.06305 = 0.04728 0.02395 0.01653 0.00683 AFIX 43 H4 2 -0.041382 0.161231 0.685685 11.00000 -1.20000 AFIX 0 C5 1 0.083291 0.346897 0.682791 11.00000 0.05324 0.06893 = 0.03136 0.00692 0.01024 0.01835 AFIX 43 H5 2 0.075395 0.370174 0.734669 11.00000 -1.20000 AFIX 0 C6 1 0.164434 0.440881 0.636779 11.00000 0.04704 0.04569 = 0.03400 -0.00157 0.00574 0.00729 AFIX 43 H6 2 0.210077 0.527335 0.656342 11.00000 -1.20000 AFIX 0 C7 1 0.254266 0.472312 0.496295 11.00000 0.03098 0.03063 = 0.03557 -0.00182 0.00001 0.00317 C8 1 0.143945 0.258694 0.449480 11.00000 0.03975 0.03211 = 0.03681 -0.00043 0.00346 -0.00557 C9 1 0.359284 0.576904 0.152927 11.00000 0.06636 0.03597 = 0.03768 -0.00037 0.01491 0.00919 AFIX 43 H9 2 0.297421 0.647325 0.175836 11.00000 -1.20000 AFIX 0 C10 1 0.390385 0.595713 0.077155 11.00000 0.07478 0.02400 = 0.03663 0.00251 0.01661 0.00679 AFIX 43 H10 2 0.350181 0.677385 0.050006 11.00000 -1.20000 AFIX 0 C11 1 0.482050 0.492741 0.040807 11.00000 0.03149 0.02643 = 0.02862 0.00072 0.00479 -0.00490 C12 1 0.535265 0.372708 0.085050 11.00000 0.04917 0.03915 = 0.04027 0.00736 0.01275 0.01292 AFIX 43 H12 2 0.594611 0.299297 0.063369 11.00000 -1.20000 AFIX 0 C13 1 0.499407 0.363539 0.161031 11.00000 0.05533 0.04470 = 0.03320 0.01136 0.01153 0.01460 AFIX 43 H13 2 0.537625 0.283337 0.190017 11.00000 -1.20000 AFIX 0 I1 3 0.323366 0.423102 0.325359 11.00000 0.03898 0.03406 = 0.03075 0.00127 0.00605 -0.00134 N1 4 0.236746 0.379995 0.433472 11.00000 0.04328 0.03076 = 0.03239 -0.00194 0.01089 -0.00819 N2 4 0.412509 0.463994 0.195230 11.00000 0.04269 0.04242 = 0.02882 0.00533 0.01111 0.00001 O1 5 0.320887 0.588547 0.498327 11.00000 0.06122 0.02829 = 0.04782 -0.00313 0.01088 -0.01077 O2 5 0.103079 0.163815 0.403345 11.00000 0.07853 0.04727 = 0.04975 -0.01245 0.01624 -0.02638 HKLF 5 REM shelxt_a.res in P2(1)/c REM R1 = 0.0374 for 2216 Fo > 4sig(Fo) and 0.0563 for all 2727 data REM 164 parameters refined using 0 restraints END WGHT 0.0064 2.4625 REM Highest difference peak 0.668, deepest hole -0.637, 1-sigma level 0.134 Q1 1 0.3077 0.4215 -0.0219 11.00000 0.05 0.67 Q2 1 0.0320 0.4226 0.3690 11.00000 0.05 0.60 Q3 1 0.3202 0.5029 0.3292 11.00000 0.05 0.57 Q4 1 0.3242 0.3441 0.3284 11.00000 0.05 0.56 Q5 1 0.1444 0.6542 0.5800 11.00000 0.05 0.51 Q6 1 0.4056 0.3659 0.2068 11.00000 0.05 0.51 Q7 1 0.1770 0.2628 0.3900 11.00000 0.05 0.50 Q8 1 0.0978 0.6477 0.1466 11.00000 0.05 0.50 Q9 1 0.3500 0.3998 0.6445 11.00000 0.05 0.49 Q10 1 0.3159 0.4280 0.0891 11.00000 0.05 0.49 Q11 1 0.6113 0.3654 0.2858 11.00000 0.05 0.48 Q12 1 0.3253 0.4471 0.6985 11.00000 0.05 0.48 Q13 1 0.5353 0.3043 0.3016 11.00000 0.05 0.48 Q14 1 0.2372 0.3425 0.3686 11.00000 0.05 0.46 Q15 1 0.2600 0.3608 0.2169 11.00000 0.05 0.46 Q16 1 -0.2598 0.0371 0.6592 11.00000 0.05 0.45 Q17 1 0.3313 0.5987 0.4157 11.00000 0.05 0.45 Q18 1 0.4815 0.3900 0.3441 11.00000 0.05 0.45 Q19 1 0.2546 0.1471 0.5778 11.00000 0.05 0.44 Q20 1 0.0389 0.0731 0.7393 11.00000 0.05 0.44 ; _shelx_res_checksum 61956 _shelx_hkl_file ; 1 0 0 691.803 21.9208 -2 1 0 0 691.803 21.9208 1 2 0 0 839.935 12.4203 -2 2 0 0 839.935 12.4203 1 3 0 0 2851.10 35.7683 -2 3 0 0 2851.10 35.7683 1 4 0 0 239.517 5.28254 -2 4 0 0 239.517 5.28254 1 5 0 0 1211.83 21.7291 -2 5 0 0 1211.83 21.7291 1 6 0 0 1195.30 25.1263 -2 6 0 0 1195.30 25.1263 1 7 0 0 47.6372 8.32584 -2 7 0 0 47.6372 8.32584 1 8 0 0 149.771 17.4570 -2 8 0 0 149.771 17.4570 1 9 0 0 130.322 21.0577 -2 9 0 0 130.322 21.0577 1 1 1 0 3896.77 36.8510 -2 1 1 0 3896.77 36.8510 1 2 1 0 656.103 6.53106 -2 2 1 0 656.103 6.53106 1 3 1 0 35.8594 1.53829 -2 3 1 0 35.8594 1.53829 1 4 1 0 677.296 7.55856 -2 4 1 0 677.296 7.55856 1 5 1 0 128.302 4.19225 -2 5 1 0 128.302 4.19225 1 6 1 0 34.7639 4.55556 -2 6 1 0 34.7639 4.55556 1 7 1 0 104.316 8.26185 -2 7 1 0 104.316 8.26185 1 8 1 0 -10.858 6.81444 -2 8 1 0 -10.858 6.81444 1 9 1 0 -5.2943 15.2274 -2 9 1 0 -5.2943 15.2274 1 0 2 0 2911.60 106.182 -2 0 2 0 2911.60 106.182 1 1 2 0 4292.75 46.1864 -2 1 2 0 4292.75 46.1864 1 2 2 0 1888.47 18.0341 -2 2 2 0 1888.47 18.0341 1 3 2 0 986.423 9.46516 -2 3 2 0 986.423 9.46516 1 4 2 0 15.6428 1.38982 -2 4 2 0 15.6428 1.38982 1 5 2 0 182.930 4.08942 -2 5 2 0 182.930 4.08942 1 6 2 0 274.834 6.24733 -2 6 2 0 274.834 6.24733 1 7 2 0 12.9603 7.01347 -2 7 2 0 12.9603 7.01347 1 8 2 0 127.083 10.0943 -2 8 2 0 127.083 10.0943 1 9 2 0 -12.791 15.6562 -2 9 2 0 -12.791 15.6562 1 0 3 0 -2.6504 2.41877 -2 0 3 0 -2.6504 2.41877 1 1 3 0 3503.70 46.9160 -2 1 3 0 3503.70 46.9160 1 2 3 0 1364.88 14.9441 -2 2 3 0 1364.88 14.9441 1 3 3 0 648.399 8.14239 -2 3 3 0 648.399 8.14239 1 4 3 0 1031.42 12.1167 -2 4 3 0 1031.42 12.1167 1 5 3 0 435.965 6.90889 -2 5 3 0 435.965 6.90889 1 6 3 0 72.2153 3.11720 -2 6 3 0 72.2153 3.11720 1 7 3 0 506.709 20.3538 -2 7 3 0 506.709 20.3538 1 8 3 0 51.5131 10.1865 -2 8 3 0 51.5131 10.1865 1 9 3 0 38.5417 11.9650 -2 9 3 0 38.5417 11.9650 1 0 4 0 1546.16 58.0293 -2 0 4 0 1546.16 58.0293 1 1 4 0 250.888 6.16890 -2 1 4 0 250.888 6.16890 1 2 4 0 285.722 4.53430 -2 2 4 0 285.722 4.53430 1 3 4 0 344.956 5.21283 -2 3 4 0 344.956 5.21283 1 4 4 0 15.1161 2.17811 -2 4 4 0 15.1161 2.17811 1 5 4 0 102.475 3.67977 -2 5 4 0 102.475 3.67977 1 6 4 0 101.917 4.67165 -2 6 4 0 101.917 4.67165 1 7 4 0 15.5206 8.06845 -2 7 4 0 15.5206 8.06845 1 8 4 0 45.0972 10.2978 -2 8 4 0 45.0972 10.2978 1 9 4 0 -9.9721 16.4060 -2 9 4 0 -9.9721 16.4060 1 0 5 0 2.71242 2.62011 -2 0 5 0 2.71242 2.62011 1 1 5 0 1160.58 20.6237 -2 1 5 0 1160.58 20.6237 1 2 5 0 662.181 9.87681 -2 2 5 0 662.181 9.87681 1 3 5 0 30.6714 1.73974 -2 3 5 0 30.6714 1.73974 1 4 5 0 239.205 4.80428 -2 4 5 0 239.205 4.80428 1 5 5 0 195.332 5.04354 -2 5 5 0 195.332 5.04354 1 6 5 0 93.5936 6.73105 -2 6 5 0 93.5936 6.73105 1 7 5 0 182.320 10.5596 -2 7 5 0 182.320 10.5596 1 8 5 0 0.57976 9.71205 -2 8 5 0 0.57976 9.71205 1 0 6 0 2706.20 53.4338 -2 0 6 0 2706.20 53.4338 1 1 6 0 485.142 9.99766 -2 1 6 0 485.142 9.99766 1 2 6 0 1366.81 19.6000 -2 2 6 0 1366.81 19.6000 1 3 6 0 1576.95 22.3309 -2 3 6 0 1576.95 22.3309 1 4 6 0 335.958 6.27428 -2 4 6 0 335.958 6.27428 1 5 6 0 245.794 6.94988 -2 5 6 0 245.794 6.94988 1 6 6 0 603.250 16.0424 -2 6 6 0 603.250 16.0424 1 7 6 0 -5.8675 7.65464 -2 7 6 0 -5.8675 7.65464 1 8 6 0 158.286 15.4683 -2 8 6 0 158.286 15.4683 1 0 7 0 1.45810 3.87980 -2 0 7 0 1.45810 3.87980 1 1 7 0 22.6323 2.43463 -2 1 7 0 22.6323 2.43463 1 2 7 0 10.3059 2.14068 -2 2 7 0 10.3059 2.14068 1 3 7 0 45.7737 3.13412 -2 3 7 0 45.7737 3.13412 1 4 7 0 14.7243 2.14915 -2 4 7 0 14.7243 2.14915 1 5 7 0 70.0826 5.90637 -2 5 7 0 70.0826 5.90637 1 6 7 0 1.58964 5.74985 -2 6 7 0 1.58964 5.74985 1 7 7 0 20.1620 7.08448 -2 7 7 0 20.1620 7.08448 1 0 8 0 397.607 12.8785 -2 0 8 0 397.607 12.8785 1 1 8 0 39.4401 2.90802 -2 1 8 0 39.4401 2.90802 1 2 8 0 219.613 5.39985 -2 2 8 0 219.613 5.39985 1 3 8 0 830.254 12.4065 -2 3 8 0 830.254 12.4065 1 4 8 0 68.0021 4.20592 -2 4 8 0 68.0021 4.20592 1 5 8 0 58.0170 6.47766 -2 5 8 0 58.0170 6.47766 1 6 8 0 156.308 9.33761 -2 6 8 0 156.308 9.33761 1 7 8 0 -4.4143 7.80063 -2 7 8 0 -4.4143 7.80063 1 0 9 0 -9.1630 4.43024 -2 0 9 0 -9.1630 4.43024 1 1 9 0 184.934 5.43483 -2 1 9 0 184.934 5.43483 1 2 9 0 228.616 5.83029 -2 2 9 0 228.616 5.83029 1 3 9 0 23.5022 3.22796 -2 3 9 0 23.5022 3.22796 1 4 9 0 292.189 9.86156 -2 4 9 0 292.189 9.86156 1 5 9 0 89.5010 6.70800 -2 5 9 0 89.5010 6.70800 1 6 9 0 9.46072 5.83596 -2 6 9 0 9.46072 5.83596 1 0 10 0 14.7790 3.59864 -2 0 10 0 14.7790 3.59864 1 1 10 0 19.5704 2.87026 -2 1 10 0 19.5704 2.87026 1 2 10 0 7.93535 3.26131 -2 2 10 0 7.93535 3.26131 1 3 10 0 36.1220 5.05699 -2 3 10 0 36.1220 5.05699 1 4 10 0 -2.9348 4.60234 -2 4 10 0 -2.9348 4.60234 1 5 10 0 2.48851 4.76143 -2 5 10 0 2.48851 4.76143 1 0 11 0 4.27075 4.10918 -2 0 11 0 4.27075 4.10918 1 1 11 0 125.875 4.97751 -2 1 11 0 125.875 4.97751 1 2 11 0 64.2017 4.49055 -2 2 11 0 64.2017 4.49055 1 3 11 0 -2.9421 3.91529 -2 3 11 0 -2.9421 3.91529 1 4 11 0 91.4878 17.3893 -2 4 11 0 91.4878 17.3893 1 0 12 0 217.878 13.3781 -2 0 12 0 217.878 13.3781 1 1 12 0 29.6490 5.37451 -2 1 12 0 29.6490 5.37451 1 9 0 1 15.9454 19.0357 -2 -9 0 1 15.9454 19.0357 1 8 0 1 -12.400 14.5192 -2 -8 0 1 -12.400 14.5192 1 7 0 1 59.8276 9.66730 -2 -7 0 1 59.8276 9.66730 1 6 0 1 36.4009 7.47167 -2 -6 0 1 36.4009 7.47167 1 5 0 1 1.37747 3.41276 -2 -5 0 1 1.37747 3.41276 1 4 0 1 0.34515 2.48730 -2 -4 0 1 0.34515 2.48730 1 3 0 1 2.56880 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6.30699 -2 0 4 18 5.22225 6.30699 1 -3 4 18 16.0855 7.01028 -2 1 4 18 16.0855 7.01028 1 -4 4 18 36.9218 8.22338 -2 2 4 18 36.9218 8.22338 1 -5 4 18 0.44116 9.73624 -2 3 4 18 0.44116 9.73624 1 2 5 18 -1.1599 12.4897 -2 -4 5 18 -1.1599 12.4897 1 1 5 18 40.9034 9.04615 -2 -3 5 18 40.9034 9.04615 1 0 5 18 89.3640 8.30562 -2 -2 5 18 89.3640 8.30562 1 -1 5 18 22.0934 6.69629 -2 -1 5 18 22.0934 6.69629 1 -2 5 18 84.8398 8.78425 -2 0 5 18 84.8398 8.78425 1 -3 5 18 43.1577 8.08736 -2 1 5 18 43.1577 8.08736 1 -4 5 18 -1.6011 7.92021 -2 2 5 18 -1.6011 7.92021 1 -5 5 18 71.4389 18.8844 -2 3 5 18 71.4389 18.8844 1 1 6 18 89.7958 11.2844 -2 -3 6 18 89.7958 11.2844 1 0 6 18 55.2690 8.35788 -2 -2 6 18 55.2690 8.35788 1 -1 6 18 243.513 11.9935 -2 -1 6 18 243.513 11.9935 1 -2 6 18 86.9487 8.93961 -2 0 6 18 86.9487 8.93961 1 -3 6 18 70.2464 9.09084 -2 1 6 18 70.2464 9.09084 1 -4 6 18 187.707 22.0046 -2 2 6 18 187.707 22.0046 1 -1 7 18 12.1949 9.07956 -2 -1 7 18 12.1949 9.07956 1 -5 0 19 -4.5052 7.98883 1 -4 0 19 9.45651 6.33117 1 -3 0 19 10.3630 4.11608 1 -2 0 19 16.8218 3.95755 1 -1 0 19 7.74086 4.13362 1 0 0 19 5.12308 4.38936 1 1 0 19 3.86482 3.99857 1 2 0 19 -1.6675 4.71330 1 3 0 19 3.44966 6.18231 1 -6 1 19 -1.4594 8.67489 1 -5 1 19 123.744 9.79769 1 -4 1 19 100.928 7.65445 1 -3 1 19 10.1139 3.56305 1 -2 1 19 142.844 8.21613 1 -1 1 19 153.031 8.15432 1 0 1 19 48.3160 5.73971 1 1 1 19 165.103 7.86680 1 2 1 19 34.0253 5.02299 1 3 1 19 46.1895 6.46151 1 -6 2 19 74.8480 14.9365 1 -5 2 19 42.0958 7.71707 1 -4 2 19 59.2600 6.94970 1 -3 2 19 104.536 7.42331 1 0 2 19 139.239 15.3700 -2 -2 2 19 139.239 15.3700 1 -1 2 19 186.591 17.0299 -2 -1 2 19 186.591 17.0299 1 0 2 19 163.375 8.63319 1 1 2 19 5.06898 4.25638 1 2 2 19 127.426 8.77679 1 3 2 19 92.1125 10.9855 1 -5 3 19 15.9944 7.62586 1 -4 3 19 11.9737 5.76752 1 -3 3 19 5.61927 4.55573 1 0 3 19 0.14517 11.0117 -2 -2 3 19 0.14517 11.0117 1 -1 3 19 1.34100 10.9630 -2 -1 3 19 1.34100 10.9630 1 0 3 19 1.10579 4.81914 1 1 3 19 0.57957 4.29255 1 2 3 19 15.1956 4.49662 1 3 3 19 -9.1712 6.85731 1 -5 4 19 18.9289 9.78709 1 -4 4 19 32.0936 6.63926 1 -3 4 19 181.775 8.26697 1 0 4 19 100.019 15.6578 -2 -2 4 19 100.019 15.6578 1 -1 4 19 130.455 16.7366 -2 -1 4 19 130.455 16.7366 1 -2 4 19 115.514 16.3351 -2 0 4 19 115.514 16.3351 1 1 4 19 19.8818 4.43628 1 -4 4 19 111.910 17.7083 -2 2 4 19 111.910 17.7083 1 -4 5 19 46.4369 8.41676 1 -3 5 19 11.9550 5.12810 1 0 5 19 132.934 17.6949 -2 -2 5 19 132.934 17.6949 1 -1 5 19 77.3338 15.6894 -2 -1 5 19 77.3338 15.6894 1 -2 5 19 112.354 17.2556 -2 0 5 19 112.354 17.2556 1 -3 5 19 82.8639 16.5738 -2 1 5 19 82.8639 16.5738 1 2 5 19 11.0999 7.47215 1 -2 6 19 13.1837 6.32797 1 -1 6 19 -7.9075 13.5798 -2 -1 6 19 -7.9075 13.5798 1 0 6 19 9.98375 5.32702 1 -5 0 20 44.5735 12.9859 1 -3 0 20 213.473 15.5482 1 -2 0 20 65.3705 10.8608 1 -1 0 20 2.45669 7.40256 1 0 0 20 142.214 9.36549 1 1 0 20 61.5906 8.39976 1 2 0 20 56.7127 8.47812 1 3 0 20 95.9658 20.1446 1 -5 1 20 -8.4971 8.62120 1 -4 1 20 73.1669 10.2115 1 -3 1 20 3.17103 3.73993 1 -2 1 20 27.7906 4.80940 1 -1 1 20 28.0790 5.05591 1 0 1 20 3.93979 3.86764 1 1 1 20 33.2098 5.93883 1 2 1 20 26.6635 6.32841 1 3 1 20 -9.5244 14.8545 1 -5 2 20 14.1325 9.75112 1 -4 2 20 31.5421 5.90683 1 -3 2 20 49.9011 5.10860 1 -2 2 20 37.2940 5.38243 1 -1 2 20 2.74151 4.02240 1 0 2 20 40.9913 5.92651 1 1 2 20 16.3536 4.68942 1 2 2 20 12.6446 5.14511 1 -4 3 20 178.770 14.7052 1 -3 3 20 47.5909 5.15762 1 -2 3 20 115.486 7.00377 1 -1 3 20 193.817 9.97856 1 0 3 20 18.2513 4.60315 1 1 3 20 139.452 9.04964 1 2 3 20 80.5858 10.9143 1 -4 4 20 4.67426 8.92717 1 -3 4 20 17.8834 4.82792 1 -2 4 20 9.80236 3.86703 1 -1 4 20 26.2811 4.74118 1 0 4 20 56.4027 7.43965 1 1 4 20 -5.9633 5.58066 1 -3 5 20 -5.9690 8.20467 1 -2 5 20 34.2451 8.14544 1 -1 5 20 43.9036 8.59145 1 0 5 20 -10.701 8.48574 1 -4 0 21 -3.5030 9.10581 1 -3 0 21 18.7658 8.42311 1 -2 0 21 28.9654 7.53672 1 -1 0 21 23.1663 9.72064 1 0 0 21 12.3211 10.2317 1 1 0 21 22.5738 12.1442 1 -4 1 21 92.5030 11.5615 1 -3 1 21 62.6113 8.02406 1 -2 1 21 55.3199 8.38125 1 -1 1 21 111.448 8.27017 1 0 1 21 30.8550 5.57288 1 1 1 21 21.0810 5.27009 1 -4 2 21 1.11453 6.66980 1 -3 2 21 75.8026 7.33339 1 -2 2 21 138.811 8.55692 1 -1 2 21 12.7237 4.52392 1 0 2 21 92.5836 8.00067 1 1 2 21 81.0906 8.71815 1 -3 3 21 5.54863 6.18167 1 -2 3 21 8.33397 4.74971 1 -1 3 21 44.5975 11.6484 1 0 3 21 -0.9895 5.15224 1 1 3 21 4.01944 8.68321 1 -2 4 21 107.497 13.1573 1 -1 4 21 -1.6083 10.4131 1 -3 0 22 15.7753 11.5757 1 -2 0 22 160.681 20.1222 1 -1 0 22 51.4851 14.6901 1 0 0 22 42.2956 13.7819 1 -2 1 22 -2.5317 7.37624 1 -1 1 22 17.0915 6.85597 1 0 1 22 5.40537 8.13414 1 -2 2 22 28.3416 9.29259 1 -1 2 22 6.97536 7.88604 1 0 0 0 0.00 0.00 0 ; _shelx_hkl_checksum 46430 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, 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 C1 C 0.1743(7) 0.3998(5) 0.5601(3) 0.0338(12) Uani 1 1 d . . . . . C2 C 0.1068(6) 0.2710(5) 0.5316(3) 0.0318(11) Uani 1 1 d . . . . . C3 C 0.0255(7) 0.1783(6) 0.5775(3) 0.0415(13) Uani 1 1 d . . . . . H3 H -0.0197 0.0914 0.5583 0.05 Uiso 1 1 calc R U . . . C4 C 0.0146(8) 0.2206(7) 0.6534(3) 0.0521(16) Uani 1 1 d . . . . . H4 H -0.0414 0.1612 0.6857 0.062 Uiso 1 1 calc R U . . . C5 C 0.0833(8) 0.3469(7) 0.6828(3) 0.0508(16) Uani 1 1 d . . . . . H5 H 0.0754 0.3702 0.7347 0.061 Uiso 1 1 calc R U . . . C6 C 0.1644(7) 0.4409(6) 0.6368(3) 0.0422(13) Uani 1 1 d . . . . . H6 H 0.2101 0.5273 0.6563 0.051 Uiso 1 1 calc R U . . . C7 C 0.2543(7) 0.4723(5) 0.4963(3) 0.0328(11) Uani 1 1 d . . . . . C8 C 0.1439(7) 0.2587(6) 0.4495(3) 0.0364(11) Uani 1 1 d . . . . . C9 C 0.3593(8) 0.5769(6) 0.1529(3) 0.0459(13) Uani 1 1 d . . . . . H9 H 0.2974 0.6473 0.1758 0.055 Uiso 1 1 calc R U . . . C10 C 0.3904(8) 0.5957(5) 0.0772(3) 0.0443(15) Uani 1 1 d . . . . . H10 H 0.3502 0.6774 0.05 0.053 Uiso 1 1 calc R U . . . C11 C 0.4821(6) 0.4927(5) 0.0408(3) 0.0288(11) Uani 1 1 d . . . . . C12 C 0.5353(8) 0.3727(6) 0.0850(3) 0.0422(14) Uani 1 1 d . . . . . H12 H 0.5946 0.2993 0.0634 0.051 Uiso 1 1 calc R U . . . C13 C 0.4994(8) 0.3635(6) 0.1610(3) 0.0439(13) Uani 1 1 d . . . . . H13 H 0.5376 0.2833 0.19 0.053 Uiso 1 1 calc R U . . . I1 I 0.32337(5) 0.42310(3) 0.32536(2) 0.03448(11) Uani 1 1 d . . . . . N1 N 0.2367(6) 0.3800(4) 0.4335(3) 0.0349(10) Uani 1 1 d . . . . . N2 N 0.4125(6) 0.4640(5) 0.1952(2) 0.0374(11) Uani 1 1 d . . . . . O1 O 0.3209(6) 0.5885(4) 0.4983(2) 0.0455(9) Uani 1 1 d . . . . . O2 O 0.1031(6) 0.1638(4) 0.4033(2) 0.0578(12) Uani 1 1 d . . . . . 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 C1 0.037(3) 0.033(3) 0.032(3) 0.002(2) 0.010(2) 0.006(2) C2 0.027(3) 0.032(3) 0.037(3) 0.001(2) 0.003(2) 0.004(2) C3 0.034(3) 0.043(3) 0.048(3) 0.014(3) 0.008(3) -0.004(2) C4 0.049(4) 0.063(4) 0.047(4) 0.024(3) 0.017(3) 0.007(3) C5 0.053(4) 0.069(4) 0.031(3) 0.007(3) 0.010(3) 0.018(3) C6 0.047(3) 0.046(3) 0.034(3) -0.002(3) 0.006(3) 0.007(3) C7 0.031(3) 0.031(2) 0.036(3) -0.002(2) 0.000(2) 0.003(2) C8 0.040(3) 0.032(3) 0.037(3) 0.000(2) 0.003(3) -0.006(2) C9 0.066(4) 0.036(3) 0.038(3) 0.000(3) 0.015(3) 0.009(3) C10 0.075(4) 0.024(3) 0.037(3) 0.003(2) 0.017(3) 0.007(3) C11 0.031(3) 0.026(2) 0.029(3) 0.001(2) 0.005(2) -0.005(2) C12 0.049(4) 0.039(3) 0.040(3) 0.007(2) 0.013(3) 0.013(3) C13 0.055(4) 0.045(3) 0.033(3) 0.011(3) 0.012(3) 0.015(3) I1 0.03898(19) 0.03406(16) 0.03075(16) 0.00127(16) 0.00605(15) -0.00134(17) N1 0.043(3) 0.031(2) 0.032(2) -0.0019(19) 0.011(2) -0.0082(19) N2 0.043(3) 0.042(2) 0.029(2) 0.005(2) 0.011(2) 0.000(2) O1 0.061(3) 0.0283(19) 0.048(2) -0.0031(17) 0.011(2) -0.0108(19) O2 0.079(3) 0.047(2) 0.050(3) -0.012(2) 0.016(2) -0.026(2) 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 0 '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 0.006 '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 C2 C1 C6 121.2(5) . . ? C2 C1 C7 107.9(4) . . ? C6 C1 C7 130.8(5) . . ? C3 C2 C1 121.7(5) . . ? C3 C2 C8 130.9(5) . . ? C1 C2 C8 107.4(4) . . ? C4 C3 C2 116.7(5) . . ? C4 C3 H3 121.7 . . ? C2 C3 H3 121.7 . . ? C5 C4 C3 122.2(6) . . ? C5 C4 H4 118.9 . . ? C3 C4 H4 118.9 . . ? C4 C5 C6 121.3(6) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? C1 C6 C5 116.8(5) . . ? C1 C6 H6 121.6 . . ? C5 C6 H6 121.6 . . ? O1 C7 N1 126.2(5) . . ? O1 C7 C1 127.3(5) . . ? N1 C7 C1 106.5(4) . . ? O2 C8 N1 124.7(5) . . ? O2 C8 C2 128.4(5) . . ? N1 C8 C2 106.9(4) . . ? N2 C9 C10 123.5(5) . . ? N2 C9 H9 118.3 . . ? C10 C9 H9 118.3 . . ? C9 C10 C11 120.0(5) . . ? C9 C10 H10 120 . . ? C11 C10 H10 120 . . ? C10 C11 C12 116.4(5) . . ? C10 C11 C11 122.2(5) . 3_665 ? C12 C11 C11 121.4(6) . 3_665 ? C13 C12 C11 119.5(5) . . ? C13 C12 H12 120.2 . . ? C11 C12 H12 120.2 . . ? N2 C13 C12 123.3(5) . . ? N2 C13 H13 118.4 . . ? C12 C13 H13 118.4 . . ? N1 I1 N2 176.79(15) . . ? C7 N1 C8 111.1(4) . . ? C7 N1 I1 124.5(3) . . ? C8 N1 I1 124.3(3) . . ? C9 N2 C13 117.3(5) . . ? C9 N2 I1 121.9(4) . . ? C13 N2 I1 120.2(4) . . ? 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 C1 C2 1.381(7) . ? C1 C6 1.388(8) . ? C1 C7 1.490(7) . ? C2 C3 1.379(7) . ? C2 C8 1.484(7) . ? C3 C4 1.380(8) . ? C3 H3 0.93 . ? C4 C5 1.368(9) . ? C4 H4 0.93 . ? C5 C6 1.386(8) . ? C5 H5 0.93 . ? C6 H6 0.93 . ? C7 O1 1.204(6) . ? C7 N1 1.381(7) . ? C8 O2 1.208(6) . ? C8 N1 1.388(6) . ? C9 N2 1.321(7) . ? C9 C10 1.369(8) . ? C9 H9 0.93 . ? C10 C11 1.390(7) . ? C10 H10 0.93 . ? C11 C12 1.393(7) . ? C11 C11 1.474(10) 3_665 ? C12 C13 1.375(8) . ? C12 H12 0.93 . ? C13 N2 1.334(7) . ? C13 H13 0.93 . ? I1 N1 2.096(4) . ? I1 N2 2.457(4) . ?