#------------------------------------------------------------------------------ #$Date: 2019-01-16 05:25:07 +0200 (Wed, 16 Jan 2019) $ #$Revision: 213115 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/24/28/2242817.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2242817 loop_ _publ_author_name 'Mahesha, Ninganayaka' 'Yathirajan, Hemmige S.' 'Furuya, Tetsundo' 'Akitsu, Takashiro' 'Glidewell, Christopher' _publ_section_title ; The crystal structure of 1-(2-iodobenzoyl)-4-(pyrimidin-2-yl)piperazine: a three-dimensional hydrogen-bonded framework, augmented by \p--\p stacking interactions and I···N halogen bonds ; _journal_coeditor_code WM5479 _journal_issue 2 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first 129 _journal_page_last 133 _journal_paper_doi 10.1107/S205698901801811X _journal_volume 75 _journal_year 2019 _chemical_formula_iupac 'C15 H15 I N4 O' _chemical_formula_moiety 'C15 H15 I N4 O' _chemical_formula_sum 'C15 H15 I N4 O' _chemical_formula_weight 394.21 _chemical_name_systematic ; 1-(2-Iodobenzoyl)-4-(pyrimidin-2-yl)piperazine ; _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2014 _cell_angle_alpha 90 _cell_angle_beta 105.155(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.6417(17) _cell_length_b 13.604(2) _cell_length_c 12.174(2) _cell_measurement_reflns_used 3152 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 27.591 _cell_measurement_theta_min 2.290 _cell_volume 1541.3(4) _computing_cell_refinement ; SAINT (Bruker, 2015) ; _computing_data_collection ; APEX2 (Bruker, 2004) ; _computing_data_reduction ; SAINT (Bruker, 2015) ; _computing_molecular_graphics ; PLATON (Spek, 2009) ; _computing_publication_material ; SHELXL2014 (Sheldrick, 2015b) and PLATON (Spek, 2009) ; _computing_structure_refinement ; SHELXL2014 (Sheldrick, 2015b) ; _computing_structure_solution ; SHELXT (Sheldrick, 2015a) ; _diffrn_ambient_temperature 173(2) _diffrn_detector_area_resol_mean 0.3333 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.966 _diffrn_measurement_device_type 'Bruker APEXII CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0669 _diffrn_reflns_av_unetI/netI 0.0632 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 8152 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.591 _diffrn_reflns_theta_min 2.290 _diffrn_source 'fine focus sealed tube' _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 2.082 _exptl_absorpt_correction_T_max 0.717 _exptl_absorpt_correction_T_min 0.345 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; (SADABS; Bruker, 2015) ; _exptl_crystal_colour colour _exptl_crystal_density_diffrn 1.699 _exptl_crystal_description plate _exptl_crystal_F_000 776 _exptl_crystal_size_max 0.670 _exptl_crystal_size_mid 0.560 _exptl_crystal_size_min 0.160 _refine_diff_density_max 0.959 _refine_diff_density_min -0.742 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 190 _refine_ls_number_reflns 3452 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.049 _refine_ls_R_factor_all 0.0294 _refine_ls_R_factor_gt 0.0276 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0235P)^2^+0.7279P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0737 _refine_ls_wR_factor_ref 0.0751 _reflns_number_gt 3188 _reflns_number_total 3452 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file wm5479sup1.cif _cod_data_source_block I _cod_database_code 2242817 _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_min 0.336 _shelx_estimated_absorpt_t_max 0.732 _shelx_hkl_file ; -1 0 0 -0.80 0.10 -2 0 0 707.83 34.60 -2 0 0 647.74 34.40 -3 0 0 0.00 0.30 -3 0 0 -0.10 0.30 -4 0 0 3923.21 199.58 -4 0 0 4067.59 199.88 -5 0 0 0.10 0.40 -5 0 0 0.30 0.40 -6 0 0 190.18 10.30 -6 0 0 192.28 10.30 -7 0 0 0.60 0.60 -7 0 0 0.70 0.60 -8 0 0 230.18 12.60 -9 0 0 -0.60 0.70 -10 0 0 148.19 8.90 -11 0 0 1.20 1.10 -12 0 0 219.68 12.80 -12 0 1 0.80 1.10 -11 0 1 32.00 3.30 -10 0 1 0.00 0.90 -9 0 1 385.66 20.40 -8 0 1 0.40 0.70 -7 0 1 1614.54 79.29 -7 0 1 1555.84 78.99 -6 0 1 -0.60 0.40 -6 0 1 -0.60 0.40 -5 0 1 1891.51 103.89 -5 0 1 1906.11 114.79 -4 0 1 0.30 0.40 -4 0 1 -0.10 0.30 -3 0 1 9981.30 509.65 -3 0 1 9999.00 519.15 -2 0 1 -1.20 0.10 -2 0 1 -0.90 0.20 -1 0 1 849.02 47.10 1 0 -1 1049.99 51.39 -1 0 -1 57.99 3.60 -2 0 -1 -1.20 0.20 -3 0 -1 164.08 8.80 -3 0 -1 168.88 8.70 -4 0 -1 1.80 0.50 -4 0 -1 0.30 0.40 -5 0 -1 1807.82 91.69 -5 0 -1 1829.42 91.69 -6 0 -1 -0.30 0.40 -6 0 -1 -0.50 0.50 -7 0 -1 968.00 49.30 -7 0 -1 981.80 49.20 -8 0 -1 -0.10 0.60 -8 0 -1 -0.20 0.70 -9 0 -1 799.22 40.80 -10 0 -1 0.10 0.80 -11 0 -1 36.80 3.60 -12 0 2 205.18 12.10 -11 0 2 0.20 1.00 -10 0 2 363.36 19.50 -9 0 2 -0.40 0.80 -8 0 2 331.57 17.60 -7 0 2 0.60 0.60 -6 0 2 931.01 46.60 -6 0 2 918.31 46.20 -5 0 2 -0.50 0.40 -5 0 2 0.90 0.40 -4 0 2 984.80 49.30 -4 0 2 988.60 49.99 -3 0 2 -0.10 0.20 3 0 -2 0.00 0.30 -2 0 2 805.82 45.00 2 0 -2 979.60 44.90 -1 0 -2 -1.40 0.20 -2 0 -2 7890.01 406.26 -4 0 -2 937.31 46.60 -4 0 -2 928.01 47.00 -5 0 -2 0.60 0.40 -5 0 -2 0.20 0.50 -6 0 -2 726.93 36.80 -6 0 -2 714.53 36.50 -7 0 -2 1.60 0.70 -7 0 -2 -0.10 0.70 -8 0 -2 9.20 1.60 -8 0 -2 11.40 1.80 -9 0 -2 -1.00 0.70 -9 0 -2 -0.30 1.10 -10 0 -2 30.00 3.10 -11 0 -2 -0.80 0.80 -12 0 3 -0.80 1.10 -11 0 3 0.50 1.10 -10 0 3 -1.00 0.90 -9 0 3 175.08 10.10 -8 0 3 -0.40 0.70 -7 0 3 273.57 14.60 -6 0 3 -0.10 0.30 -6 0 3 0.10 0.60 -5 0 3 5263.47 263.37 -4 0 3 -1.80 0.30 -3 0 3 1132.99 73.59 3 0 -3 1299.87 67.29 -1 0 3 4889.11 257.67 0 0 3 -3.40 0.20 -1 0 -3 1415.46 72.09 -2 0 -3 -3.20 0.30 -3 0 -3 166.88 8.80 -4 0 -3 0.00 0.50 -4 0 -3 -0.50 0.30 -5 0 -3 948.81 47.10 -5 0 -3 929.21 47.60 -6 0 -3 0.50 0.50 -6 0 -3 -0.60 0.70 -7 0 -3 427.76 22.40 -7 0 -3 436.36 22.90 -8 0 -3 0.20 0.70 -8 0 -3 -0.70 0.80 -9 0 -3 640.44 33.20 -9 0 -3 630.24 32.80 -10 0 -3 0.40 0.90 -11 0 -3 190.88 11.40 -12 0 4 237.98 13.80 -11 0 4 -0.80 1.00 -10 0 4 449.26 23.90 -9 0 4 0.30 0.90 -8 0 4 812.02 41.50 -6 0 4 552.74 28.30 -5 0 4 -0.20 0.50 5 0 -4 0.00 0.30 -4 0 4 457.45 24.10 4 0 -4 489.35 23.80 -3 0 4 -1.30 0.30 3 0 -4 -0.70 0.30 -2 0 4 813.72 42.20 2 0 -4 864.31 41.90 -1 0 4 -0.40 0.30 0 0 4 1667.23 83.29 -1 0 -4 1.30 0.30 -2 0 -4 1417.96 71.19 -4 0 -4 4476.55 223.48 -5 0 -4 2.40 0.70 -5 0 -4 0.70 0.80 -6 0 -4 114.69 6.70 -6 0 -4 117.49 7.30 -7 0 -4 0.70 0.70 -7 0 -4 -0.30 0.90 -8 0 -4 298.67 16.40 -8 0 -4 313.07 17.10 -9 0 -4 -0.70 1.00 -9 0 -4 -0.50 0.80 -12 0 5 0.20 1.30 -11 0 5 6.40 1.80 -10 0 5 -0.50 1.00 -9 0 5 0.40 1.00 -8 0 5 -0.60 0.80 -7 0 5 189.88 10.60 -6 0 5 0.20 0.60 -5 0 5 1513.15 75.89 5 0 -5 1508.85 75.79 -4 0 5 -0.10 0.40 4 0 -5 0.00 0.30 -3 0 5 2500.55 133.19 3 0 -5 2822.02 135.69 -2 0 5 -0.50 0.40 2 0 -5 -1.70 0.40 -1 0 5 2517.05 125.89 0 0 5 -0.50 0.20 -1 0 -5 2454.95 122.39 -2 0 -5 0.60 0.30 -3 0 -5 2.40 0.50 -5 0 -5 83.49 5.70 -5 0 -5 82.29 4.90 -6 0 -5 0.50 0.90 -6 0 -5 0.30 0.60 -7 0 -5 539.45 28.60 -7 0 -5 574.84 29.60 -8 0 -5 -0.50 1.00 -8 0 -5 -0.30 0.70 -9 0 -5 380.56 21.10 -10 0 -5 -0.70 1.20 -12 0 6 111.59 7.80 -11 0 6 -1.40 1.10 -10 0 6 386.06 20.90 -9 0 6 -0.40 0.90 -8 0 6 1258.57 63.59 -7 0 6 0.00 0.80 -6 0 6 503.05 25.80 6 0 -6 497.45 25.30 -5 0 6 0.40 0.50 5 0 -6 2.70 0.50 -4 0 6 1232.78 66.89 4 0 -6 1340.77 64.69 -3 0 6 -0.60 0.40 3 0 -6 -1.30 0.30 -2 0 6 287.87 14.20 2 0 -6 262.27 14.20 -1 0 6 -0.30 0.40 0 0 6 2957.70 147.79 -1 0 -6 1.40 0.30 -2 0 -6 231.98 11.90 -3 0 -6 0.50 0.40 -4 0 -6 3000.90 148.49 -4 0 -6 2927.81 148.19 -5 0 -6 1.20 0.60 -5 0 -6 -0.10 0.70 -6 0 -6 1150.58 59.49 -6 0 -6 1220.38 60.69 -7 0 -6 -0.40 0.70 -7 0 -6 0.10 1.20 -8 0 -6 314.37 17.90 -9 0 -6 -1.20 1.10 -11 0 7 179.48 11.00 -10 0 7 0.30 1.20 -9 0 7 112.59 7.30 -8 0 7 -0.70 0.90 -7 0 7 24.20 2.50 7 0 -7 21.50 1.80 -6 0 7 0.10 0.70 6 0 -7 0.80 0.50 -5 0 7 99.49 6.00 5 0 -7 106.39 5.60 -3 0 7 2367.26 118.69 3 0 -7 2371.96 118.39 -2 0 7 0.30 0.40 2 0 -7 -0.10 0.60 -1 0 7 2677.43 134.09 0 0 7 -0.30 0.30 -1 0 -7 1679.73 84.29 -2 0 -7 0.50 0.30 -3 0 -7 888.41 44.50 -4 0 -7 0.20 0.50 -4 0 -7 -0.30 0.80 -5 0 -7 216.28 11.80 -5 0 -7 224.78 13.00 -6 0 -7 -0.40 1.10 -7 0 -7 128.69 8.80 -8 0 -7 -0.30 1.30 -9 0 -7 134.69 9.50 -11 0 8 -0.10 1.30 -10 0 8 173.68 10.60 -9 0 8 0.60 1.20 -8 0 8 427.86 22.70 -6 0 8 1236.88 62.79 6 0 -8 1259.17 62.19 -5 0 8 0.00 0.60 5 0 -8 0.30 0.40 -4 0 8 508.85 26.50 4 0 -8 530.35 26.20 -3 0 8 0.70 0.60 3 0 -8 0.50 0.60 -2 0 8 797.22 40.10 -1 0 8 2.10 0.60 -1 0 -8 1.40 0.40 -2 0 -8 313.47 16.00 -3 0 -8 0.70 0.50 -3 0 -8 -0.10 0.90 -4 0 -8 531.95 28.00 -4 0 -8 568.34 29.30 -5 0 -8 -0.30 1.00 -6 0 -8 925.41 48.30 -7 0 -8 1.10 1.40 -8 0 -8 211.78 13.40 -11 0 9 53.79 4.90 -10 0 9 0.10 1.40 -9 0 9 544.45 28.80 -8 0 9 0.90 1.30 8 0 -9 0.70 0.70 -7 0 9 18.30 2.40 7 0 -9 12.30 1.50 -6 0 9 0.90 0.80 6 0 -9 0.70 0.50 -5 0 9 17.50 2.00 5 0 -9 16.00 1.50 -4 0 9 4.00 0.90 4 0 -9 4.30 0.90 -3 0 9 175.18 9.50 3 0 -9 173.48 9.40 -2 0 9 0.40 0.50 -1 0 9 1572.74 78.59 0 0 -9 0.10 0.40 -1 0 -9 1403.16 71.09 -2 0 -9 -0.20 0.90 -2 0 -9 0.40 0.40 -3 0 -9 691.23 36.20 -4 0 -9 -0.40 1.00 -5 0 -9 227.28 13.80 -6 0 -9 -0.60 1.20 -7 0 -9 41.80 5.00 -11 0 10 -1.20 1.50 -10 0 10 38.10 4.20 -9 0 10 0.30 1.30 -8 0 10 282.57 15.10 8 0 -10 257.27 14.10 -7 0 10 0.20 1.00 7 0 -10 0.40 0.60 -6 0 10 543.25 28.50 6 0 -10 561.44 28.00 -5 0 10 0.80 0.80 5 0 -10 -0.10 0.60 -4 0 10 1136.79 58.79 4 0 -10 1204.58 58.59 -3 0 10 0.70 0.70 3 0 -10 4.40 1.10 -2 0 10 456.55 23.40 0 0 -10 410.56 20.90 -1 0 -10 0.30 0.90 -1 0 -10 2.70 0.80 -2 0 -10 18.60 2.80 -3 0 -10 -0.80 0.90 -4 0 -10 126.19 8.70 -5 0 -10 -1.00 1.20 -6 0 -10 247.68 15.20 -10 0 11 -0.20 1.50 -9 0 11 208.78 12.30 -8 0 11 -0.30 1.10 -7 0 11 264.57 14.60 7 0 -11 264.37 13.90 -6 0 11 0.00 0.90 6 0 -11 0.50 0.60 -5 0 11 1.90 1.00 5 0 -11 3.30 0.90 -4 0 11 0.10 0.70 -3 0 11 70.39 4.50 3 0 -11 72.99 4.70 -2 0 11 1.00 0.70 -1 0 11 189.78 10.20 0 0 -11 0.10 0.90 -1 0 -11 809.92 42.00 -2 0 -11 -0.50 0.90 -3 0 -11 663.43 35.20 -4 0 -11 -0.20 1.20 -5 0 -11 248.58 15.20 -6 0 -11 -0.60 2.30 -10 0 12 2.30 1.60 -9 0 12 -0.20 1.40 -8 0 12 35.30 3.70 -7 0 12 0.40 1.10 -6 0 12 704.03 36.20 -5 0 12 0.10 0.90 5 0 -12 0.60 0.80 -4 0 12 358.86 19.70 4 0 -12 393.16 19.60 -3 0 12 0.30 0.70 3 0 -12 -0.40 1.00 2 0 -12 669.33 34.30 1 0 -12 0.10 0.90 0 0 -12 529.55 28.20 -1 0 -12 -0.50 1.00 -2 0 -12 35.70 4.00 -3 0 -12 -0.90 1.10 -4 0 -12 3.20 1.70 -5 0 -12 -1.30 2.10 -9 0 13 450.65 24.40 -8 0 13 -1.10 1.20 -7 0 13 46.30 4.10 -6 0 13 0.10 1.00 -5 0 13 560.24 29.00 3 0 -13 1.70 1.20 2 0 -13 1.50 1.20 0 0 -13 0.00 1.10 -1 0 -13 192.38 11.80 -2 0 -13 -0.50 1.10 -3 0 -13 326.47 18.90 -8 0 14 6.60 1.80 -7 0 14 0.00 1.20 0 0 -14 214.38 13.00 -1 0 -14 -0.90 1.10 -2 0 -14 234.18 14.30 -7 -1 15 -0.20 1.20 -2 1 -14 52.99 5.10 -1 1 -14 57.79 5.20 0 1 -14 86.99 6.50 -5 -1 14 100.89 6.40 -6 -1 14 148.59 8.90 -7 -1 14 16.60 2.60 -8 -1 14 109.29 7.40 -3 1 -13 1.70 1.50 -2 1 -13 113.69 8.00 -1 1 -13 109.69 7.70 0 1 -13 73.99 5.80 -3 -1 13 165.18 9.40 -4 -1 13 -0.50 0.80 -5 -1 13 328.77 17.60 -6 -1 13 133.49 8.10 -7 -1 13 16.80 2.70 -8 -1 13 98.29 6.80 -9 -1 13 5.10 1.80 -4 1 -12 163.18 10.80 -3 1 -12 5.80 1.90 -2 1 -12 229.98 13.70 2 1 -12 70.99 4.80 -2 -1 12 65.99 4.40 3 1 -12 759.82 38.00 -3 -1 12 699.93 37.10 -4 -1 12 14.20 2.00 -5 -1 12 35.50 3.10 -6 -1 12 92.29 6.00 -7 -1 12 80.39 5.60 -8 -1 12 123.79 8.00 -9 -1 12 23.90 3.40 -10 -1 12 159.48 10.30 -5 1 -11 33.90 4.40 -4 1 -11 206.98 12.90 -3 1 -11 1.60 1.30 0 1 -11 323.27 16.80 -1 -1 11 288.27 15.10 -2 -1 11 49.00 3.40 3 1 -11 383.76 19.50 -3 -1 11 365.66 19.50 4 1 -11 12.20 1.60 -4 -1 11 9.60 1.80 -5 -1 11 481.15 25.00 -6 -1 11 39.70 3.40 -7 -1 11 82.69 5.70 -8 -1 11 96.49 6.60 -9 -1 11 72.89 5.70 -10 -1 11 90.49 6.70 -6 1 -10 155.08 10.60 -5 1 -10 211.28 13.10 -4 1 -10 191.38 11.90 -2 1 -10 652.03 32.90 -1 1 -10 20.70 1.80 0 1 -10 524.65 26.70 -1 -1 10 151.48 8.30 -2 -1 10 248.18 13.10 3 1 -10 492.25 24.90 -3 -1 10 482.45 25.00 4 1 -10 91.99 5.10 -4 -1 10 83.49 5.40 5 1 -10 433.16 20.80 -5 -1 10 381.56 21.20 6 1 -10 84.99 4.80 -6 -1 10 84.89 5.50 -7 -1 10 155.48 9.20 -8 -1 10 130.59 8.20 -9 -1 10 166.88 10.20 -10 -1 10 331.67 18.50 -11 -1 10 6.00 2.10 -7 1 -9 239.88 14.80 -6 1 -9 11.10 2.40 -5 1 -9 417.96 23.20 -4 1 -9 356.96 18.80 -3 1 -9 177.28 9.60 -2 1 -9 408.16 20.80 -1 1 -9 6.00 1.00 0 1 -9 474.35 24.10 -1 -1 9 4.80 0.90 -2 -1 9 429.46 22.00 3 1 -9 609.24 30.10 -3 -1 9 579.24 30.20 4 1 -9 219.68 11.20 -4 -1 9 207.18 11.50 5 1 -9 939.31 45.50 -5 -1 9 882.01 46.00 6 1 -9 24.20 1.80 -6 -1 9 22.90 2.50 7 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47.00 4.20 -6 -15 0 99.59 9.10 4 -15 -1 212.98 12.70 3 -15 -1 40.90 4.00 2 -15 -1 119.49 7.70 1 -15 -1 54.39 4.30 0 -15 -1 7.20 1.40 -1 -15 -1 189.88 10.70 -2 -15 -1 40.70 3.50 -3 -15 -1 75.69 5.30 -4 -15 -1 166.98 9.80 -5 -15 -1 32.10 3.60 3 -15 -2 115.49 7.50 2 -15 -2 31.80 3.30 1 -15 -2 169.98 9.80 0 -15 -2 38.90 3.30 -1 -15 -2 509.35 26.40 -2 -15 -2 4.60 1.30 -3 -15 -2 396.16 21.00 -4 -15 -2 44.00 4.20 -5 -15 -2 166.38 10.40 3 -15 -3 9.70 1.90 2 -15 -3 368.36 19.60 1 -15 -3 43.80 3.60 0 -15 -3 98.09 6.10 -1 -15 -3 82.39 5.50 -2 -15 -3 20.70 2.70 -3 -15 -3 120.39 7.70 -4 -15 -3 66.79 5.40 2 -15 -4 79.69 5.30 1 -15 -4 118.29 7.10 0 -15 -4 28.70 2.80 -1 -15 -4 259.57 14.20 -2 -15 -4 1.70 1.20 -3 -15 -4 366.96 19.80 -4 -15 -4 5.20 1.90 1 -15 -5 2.50 1.00 0 -15 -5 144.09 8.40 -1 -15 -5 96.19 6.20 -2 -15 -5 262.57 14.60 -3 -15 -5 109.59 7.40 5 -15 -6 80.19 5.30 1 -15 -6 2.70 1.10 0 -15 -6 125.59 7.60 -1 -15 -6 57.59 4.50 -2 -15 -6 24.30 3.40 5 -15 -7 54.39 4.10 4 -15 -7 133.19 7.80 3 -15 -7 16.70 2.20 0 -15 -7 158.68 9.30 -1 -15 -7 9.50 1.80 -2 -15 -7 222.18 14.80 3 -15 -8 126.59 7.50 2 -15 -8 4.40 1.30 1 -15 -8 30.00 3.50 0 -15 -8 80.39 5.90 -1 16 -6 89.19 5.80 0 16 -6 5.60 1.30 1 16 -6 231.68 12.60 -2 16 -5 181.38 10.40 -1 16 -5 28.30 2.80 0 16 -5 82.59 6.10 -1 -16 5 61.29 5.70 -2 -16 5 -0.20 1.20 -3 -16 5 0.30 1.30 -3 16 -4 0.40 1.00 -2 16 -4 15.60 2.30 0 -16 4 7.70 2.00 -1 -16 4 174.78 11.20 -2 -16 4 4.30 1.70 -3 -16 4 332.07 18.70 -4 -16 4 12.20 2.30 -4 16 -3 237.68 13.60 1 -16 3 0.60 1.20 0 -16 3 311.27 17.80 -1 -16 3 16.20 2.90 -2 -16 3 29.90 3.60 -3 -16 3 11.30 2.10 -4 -16 3 4.50 1.50 2 -16 2 3.10 1.50 1 -16 2 1.10 1.20 0 -16 2 30.60 3.60 -1 -16 2 270.17 15.40 -2 -16 2 35.70 3.80 -3 -16 2 174.58 10.50 -4 -16 2 56.19 4.70 2 -16 1 332.17 18.70 1 -16 1 6.90 1.80 0 -16 1 356.86 19.60 -1 -16 1 1.90 1.20 -2 -16 1 330.87 18.00 -3 -16 1 30.00 3.40 -4 -16 1 36.30 3.70 3 -16 0 111.99 7.80 2 -16 0 29.70 3.60 1 -16 0 32.90 3.60 0 -16 0 25.60 3.10 -1 -16 0 31.80 3.30 -2 -16 0 34.20 3.50 -3 -16 0 145.89 8.80 -4 -16 0 31.00 3.50 3 -16 -1 26.20 3.40 2 -16 -1 301.07 16.80 1 -16 -1 2.70 1.20 0 -16 -1 355.76 19.10 -1 -16 -1 8.30 1.60 -2 -16 -1 396.16 21.00 -3 -16 -1 10.30 1.80 -4 -16 -1 195.88 11.90 3 -16 -2 158.48 9.80 2 -16 -2 34.60 3.50 1 -16 -2 267.07 14.80 0 -16 -2 32.50 3.30 -1 -16 -2 0.80 1.00 -2 -16 -2 4.20 1.30 -3 -16 -2 4.90 1.50 2 -16 -3 33.00 3.30 1 -16 -3 19.90 2.60 0 -16 -3 322.97 17.30 -1 -16 -3 0.60 1.00 -2 -16 -3 223.58 12.60 -3 -16 -3 4.00 1.50 2 -16 -4 2.40 1.10 1 -16 -4 184.78 10.50 0 -16 -4 12.90 2.30 -1 -16 -4 140.59 8.40 -2 -16 -4 22.10 3.00 1 -16 -5 75.69 5.20 0 -16 -5 114.09 7.10 -1 -16 -5 37.80 3.60 1 -16 -6 242.78 14.30 0 -16 -6 7.30 1.50 -1 -16 -6 109.69 7.30 1 -17 2 34.90 4.10 0 -17 2 63.09 5.40 -1 -17 2 146.99 9.60 2 -17 1 0.50 1.20 1 -17 1 149.19 9.60 0 -17 1 4.30 1.50 -1 -17 1 211.78 12.40 -2 -17 1 3.70 1.80 3 -17 0 76.19 6.10 2 -17 0 55.19 5.00 1 -17 0 54.69 4.80 0 -17 0 1.00 1.10 -1 -17 0 54.29 4.60 3 -17 -1 38.80 4.10 2 -17 -1 3.50 1.50 1 -17 -1 206.88 12.10 0 -17 -1 5.00 1.40 -1 -17 -1 170.68 10.10 2 -17 -2 36.50 3.80 1 -17 -2 157.48 9.50 0 -17 -2 71.99 5.30 -1 -17 -2 40.60 3.80 2 -17 -3 72.09 5.40 1 -17 -3 133.29 8.20 0 -17 -3 3.10 1.20 -1 -17 -3 157.78 10.60 1 -17 -4 93.79 6.20 0 -17 -4 33.50 3.30 _computing_structure_solution 'SHELXT 2014/4 (Sheldrick, 2014)' ; _shelx_hkl_checksum 2696 _shelx_res_file ; TITL m22cg CELL 0.71073 9.6417 13.604 12.174 90.000 105.155 90.000 ZERR 4 0.0017 0.002 0.002 0.000 0.002 0.000 LATT 1 SYMM 0.50000 - X , 0.50000 + Y , 0.50000 - Z SFAC C H I N O UNIT 60 60 4 16 4 TEMP -100 SIZE 0.16 0.56 0.67 OMIT -2 180.0 L.S. 20 FMAP 2 PLAN 20 ACTA BOND $H CONF HTAB WGHT 0.023500 0.727900 FVAR 0.38625 N1 4 0.238830 0.449844 0.525389 11.00000 0.04176 0.01709 = 0.01802 -0.00250 0.00949 0.00263 C2 1 0.226303 0.364474 0.595039 11.00000 0.04547 0.01900 = 0.02472 -0.00285 0.01717 -0.00725 AFIX 23 H2A 2 0.256658 0.304614 0.561322 11.00000 -1.20000 H2B 2 0.124787 0.355923 0.596368 11.00000 -1.20000 AFIX 0 C3 1 0.319534 0.377774 0.715908 11.00000 0.04961 0.01933 = 0.02114 0.00164 0.01492 0.00300 AFIX 23 H3A 2 0.303348 0.322535 0.764030 11.00000 -1.20000 H3B 2 0.422197 0.377739 0.715857 11.00000 -1.20000 AFIX 0 N4 4 0.283904 0.470434 0.762292 11.00000 0.04206 0.02127 = 0.01607 -0.00120 0.01007 0.00088 C5 1 0.297744 0.556096 0.692569 11.00000 0.03773 0.01913 = 0.01817 -0.00224 0.00883 0.00135 AFIX 23 H5A 2 0.399127 0.563669 0.690431 11.00000 -1.20000 H5B 2 0.268866 0.616324 0.726541 11.00000 -1.20000 AFIX 0 C6 1 0.202769 0.542627 0.572334 11.00000 0.04114 0.02231 = 0.01805 -0.00426 0.00686 0.00585 AFIX 23 H6A 2 0.100500 0.542063 0.573534 11.00000 -1.20000 H6B 2 0.217434 0.598033 0.523853 11.00000 -1.20000 AFIX 0 C17 1 0.292866 0.450257 0.434040 11.00000 0.03036 0.01763 = 0.01243 -0.00197 0.00073 0.00054 O17 5 0.311772 0.525522 0.384482 11.00000 0.06461 0.01728 = 0.01963 0.00141 0.01328 0.00129 C11 1 0.332832 0.352682 0.391086 11.00000 0.03017 0.01450 = 0.01504 0.00137 0.00786 -0.00060 C12 1 0.243438 0.306921 0.296249 11.00000 0.02626 0.01745 = 0.01526 0.00026 0.00837 -0.00167 I12 3 0.037087 0.361860 0.218501 11.00000 0.02670 0.02407 = 0.02409 -0.00347 0.00387 -0.00088 C13 1 0.288254 0.222264 0.250978 11.00000 0.04214 0.01634 = 0.02178 -0.00164 0.01406 -0.00103 AFIX 43 H13 2 0.226789 0.190894 0.186746 11.00000 -1.20000 AFIX 0 C14 1 0.423745 0.184275 0.300798 11.00000 0.04914 0.01915 = 0.03742 0.00054 0.02495 0.00704 AFIX 43 H14 2 0.455287 0.126941 0.269870 11.00000 -1.20000 AFIX 0 C15 1 0.513048 0.228887 0.394717 11.00000 0.03449 0.03041 = 0.04081 0.00833 0.01324 0.01076 AFIX 43 H15 2 0.605388 0.202122 0.428400 11.00000 -1.20000 AFIX 0 C16 1 0.467716 0.313139 0.440060 11.00000 0.03132 0.02612 = 0.02379 0.00201 0.00307 0.00086 AFIX 43 H16 2 0.529263 0.343775 0.504803 11.00000 -1.20000 AFIX 0 N41 4 0.276925 0.571579 0.913998 11.00000 0.03780 0.03425 = 0.01863 -0.00432 0.00815 0.00822 C42 1 0.302491 0.481721 0.877839 11.00000 0.02145 0.02865 = 0.01743 -0.00092 0.00704 -0.00278 N43 4 0.341440 0.401757 0.943486 11.00000 0.03681 0.02789 = 0.02139 0.00192 0.01149 -0.00549 C44 1 0.352797 0.414959 1.054529 11.00000 0.03843 0.03878 = 0.02236 0.00635 0.00992 -0.00920 AFIX 43 H44 2 0.378975 0.360089 1.103876 11.00000 -1.20000 AFIX 0 C45 1 0.328764 0.503320 1.101246 11.00000 0.03509 0.04518 = 0.01691 -0.00234 0.00981 -0.00728 AFIX 43 H45 2 0.338150 0.510794 1.180444 11.00000 -1.20000 AFIX 0 C46 1 0.290161 0.580425 1.025821 11.00000 0.03998 0.04280 = 0.01993 -0.00598 0.01023 0.00343 AFIX 43 H46 2 0.272125 0.642714 1.054560 11.00000 -1.20000 AFIX 0 HKLF 4 REM m22cg REM R1 = 0.0276 for 3188 Fo > 4sig(Fo) and 0.0294 for all 3452 data REM 190 parameters refined using 0 restraints END WGHT 0.0235 0.7278 REM Instructions for potential hydrogen bonds EQIV $1 -x, -y+1, -z+1 HTAB C5 I12_$1 EQIV $2 -x+1/2, y-1/2, -z+1/2 HTAB C13 O17_$2 EQIV $3 x, y, z+1 HTAB C45 O17_$3 REM Highest difference peak 0.959, deepest hole -0.742, 1-sigma level 0.092 Q1 1 0.0822 0.3604 0.2889 11.00000 0.05 0.96 Q2 1 -0.0199 0.3610 0.1531 11.00000 0.05 0.84 Q3 1 0.0716 0.3127 0.1914 11.00000 0.05 0.76 Q4 1 0.0047 0.3130 0.2578 11.00000 0.05 0.72 Q5 1 0.0832 0.4109 0.1840 11.00000 0.05 0.70 Q6 1 0.0584 0.4167 0.2011 11.00000 0.05 0.69 Q7 1 0.0303 0.3017 0.2324 11.00000 0.05 0.68 Q8 1 -0.0262 0.2834 0.1685 11.00000 0.05 0.61 Q9 1 0.0065 0.4129 0.2649 11.00000 0.05 0.52 Q10 1 -0.0218 0.4390 0.1605 11.00000 0.05 0.49 Q11 1 0.1175 0.4513 0.2922 11.00000 0.05 0.47 Q12 1 0.3186 0.4001 0.4030 11.00000 0.05 0.45 Q13 1 0.1506 0.6402 0.8752 11.00000 0.05 0.44 Q14 1 0.2229 0.4968 0.5419 11.00000 0.05 0.42 Q15 1 0.1073 0.2732 0.2618 11.00000 0.05 0.42 Q16 1 0.2242 0.3630 0.3171 11.00000 0.05 0.42 Q17 1 0.1072 0.2770 0.2911 11.00000 0.05 0.40 Q18 1 0.2468 0.5480 0.6319 11.00000 0.05 0.38 Q19 1 0.3002 0.3412 0.3205 11.00000 0.05 0.37 Q20 1 0.2783 0.3738 0.6551 11.00000 0.05 0.36 ; _shelx_res_checksum 1018 _shelxl_version_number 2.014 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_occupancy N N1 0.2388(2) 0.44984(14) 0.52539(16) 0.0253(4) Uani d 1 C C2 0.2263(3) 0.36447(15) 0.5950(2) 0.0282(6) Uani d 1 H H2A 0.2567 0.3046 0.5613 0.034 Uiso calc 1 H H2B 0.1248 0.3559 0.5964 0.034 Uiso calc 1 C C3 0.3195(3) 0.37777(17) 0.7159(2) 0.0290(6) Uani d 1 H H3A 0.3033 0.3225 0.7640 0.035 Uiso calc 1 H H3B 0.4222 0.3777 0.7159 0.035 Uiso calc 1 N N4 0.2839(2) 0.47043(14) 0.76229(16) 0.0260(4) Uani d 1 C C5 0.2977(3) 0.55610(16) 0.69257(18) 0.0247(5) Uani d 1 H H5A 0.3991 0.5637 0.6904 0.030 Uiso calc 1 H H5B 0.2689 0.6163 0.7265 0.030 Uiso calc 1 C C6 0.2028(3) 0.54263(17) 0.57233(19) 0.0273(5) Uani d 1 H H6A 0.1005 0.5421 0.5735 0.033 Uiso calc 1 H H6B 0.2174 0.5980 0.5239 0.033 Uiso calc 1 C C17 0.2929(3) 0.45026(16) 0.43404(17) 0.0211(4) Uani d 1 O O17 0.3118(2) 0.52552(12) 0.38448(14) 0.0334(4) Uani d 1 C C11 0.3328(3) 0.35268(15) 0.39109(19) 0.0195(5) Uani d 1 C C12 0.2434(2) 0.30692(15) 0.29625(17) 0.0191(4) Uani d 1 I I12 0.03709(2) 0.36186(2) 0.21850(2) 0.02547(8) Uani d 1 C C13 0.2883(3) 0.22226(16) 0.25098(19) 0.0257(5) Uani d 1 H H13 0.2268 0.1909 0.1867 0.031 Uiso calc 1 C C14 0.4237(3) 0.18428(17) 0.3008(2) 0.0327(6) Uani d 1 H H14 0.4553 0.1269 0.2699 0.039 Uiso calc 1 C C15 0.5130(3) 0.22889(19) 0.3947(2) 0.0346(6) Uani d 1 H H15 0.6054 0.2021 0.4284 0.042 Uiso calc 1 C C16 0.4677(3) 0.31314(18) 0.4401(2) 0.0279(5) Uani d 1 H H16 0.5293 0.3438 0.5048 0.033 Uiso calc 1 N N41 0.2769(2) 0.57158(16) 0.91400(17) 0.0301(5) Uani d 1 C C42 0.3025(2) 0.48172(17) 0.87784(18) 0.0221(4) Uani d 1 N N43 0.3414(2) 0.40176(15) 0.94349(17) 0.0280(4) Uani d 1 C C44 0.3528(3) 0.4150(2) 1.0545(2) 0.0328(6) Uani d 1 H H44 0.3790 0.3601 1.1039 0.039 Uiso calc 1 C C45 0.3288(3) 0.5033(2) 1.1012(2) 0.0318(6) Uani d 1 H H45 0.3381 0.5108 1.1804 0.038 Uiso calc 1 C C46 0.2902(3) 0.5804(2) 1.0258(2) 0.0338(6) Uani d 1 H H46 0.2721 0.6427 1.0546 0.041 Uiso calc 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 N1 0.0418(12) 0.0171(8) 0.0180(9) 0.0026(9) 0.0095(8) -0.0025(7) C2 0.0455(17) 0.0190(11) 0.0247(13) -0.0072(10) 0.0172(12) -0.0029(8) C3 0.0496(17) 0.0193(10) 0.0211(12) 0.0030(12) 0.0149(11) 0.0016(9) N4 0.0421(12) 0.0213(9) 0.0161(9) 0.0009(10) 0.0101(8) -0.0012(7) C5 0.0377(13) 0.0191(10) 0.0182(11) 0.0013(11) 0.0088(9) -0.0022(8) C6 0.0411(14) 0.0223(10) 0.0181(10) 0.0059(11) 0.0069(10) -0.0043(9) C17 0.0304(11) 0.0176(9) 0.0124(9) 0.0005(10) 0.0007(8) -0.0020(8) O17 0.0646(13) 0.0173(7) 0.0196(8) 0.0013(9) 0.0133(8) 0.0014(6) C11 0.0302(12) 0.0145(9) 0.0150(10) -0.0006(9) 0.0079(9) 0.0014(7) C12 0.0263(11) 0.0174(9) 0.0153(9) -0.0017(9) 0.0084(8) 0.0003(8) I12 0.02670(12) 0.02407(11) 0.02409(11) -0.00088(5) 0.00387(8) -0.00347(5) C13 0.0421(14) 0.0163(10) 0.0218(11) -0.0010(11) 0.0141(10) -0.0016(8) C14 0.0491(16) 0.0192(11) 0.0374(14) 0.0070(12) 0.0250(12) 0.0005(10) C15 0.0345(13) 0.0304(13) 0.0408(14) 0.0108(13) 0.0132(11) 0.0083(11) C16 0.0313(12) 0.0261(11) 0.0238(11) 0.0009(11) 0.0031(9) 0.0020(9) N41 0.0378(12) 0.0343(11) 0.0186(10) 0.0082(10) 0.0081(8) -0.0043(8) C42 0.0214(10) 0.0286(11) 0.0174(10) -0.0028(10) 0.0070(8) -0.0009(9) N43 0.0368(12) 0.0279(10) 0.0214(10) -0.0055(10) 0.0115(8) 0.0019(8) C44 0.0384(14) 0.0388(14) 0.0224(12) -0.0092(13) 0.0099(10) 0.0063(10) C45 0.0351(13) 0.0452(14) 0.0169(11) -0.0073(13) 0.0098(9) -0.0023(10) C46 0.0400(14) 0.0428(14) 0.0199(12) 0.0034(13) 0.0102(10) -0.0060(11) 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' 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 C17 N1 C2 126.25(18) C17 N1 C6 120.10(19) C2 N1 C6 113.23(17) N1 C2 C3 110.4(2) N1 C2 H2A 109.6 C3 C2 H2A 109.6 N1 C2 H2B 109.6 C3 C2 H2B 109.6 H2A C2 H2B 108.1 N4 C3 C2 109.7(2) N4 C3 H3A 109.7 C2 C3 H3A 109.7 N4 C3 H3B 109.7 C2 C3 H3B 109.7 H3A C3 H3B 108.2 C42 N4 C3 120.7(2) C42 N4 C5 119.60(18) C3 N4 C5 113.33(17) N4 C5 C6 109.75(19) N4 C5 H5A 109.7 C6 C5 H5A 109.7 N4 C5 H5B 109.7 C6 C5 H5B 109.7 H5A C5 H5B 108.2 N1 C6 C5 109.6(2) N1 C6 H6A 109.8 C5 C6 H6A 109.8 N1 C6 H6B 109.8 C5 C6 H6B 109.8 H6A C6 H6B 108.2 O17 C17 N1 123.3(2) O17 C17 C11 118.59(19) N1 C17 C11 118.07(19) C16 C11 C12 119.3(2) C16 C11 C17 119.1(2) C12 C11 C17 121.3(2) C13 C12 C11 120.5(2) C13 C12 I12 118.05(18) C11 C12 I12 121.41(16) C14 C13 C12 119.2(2) C14 C13 H13 120.4 C12 C13 H13 120.4 C15 C14 C13 120.7(2) C15 C14 H14 119.6 C13 C14 H14 119.6 C14 C15 C16 119.9(2) C14 C15 H15 120.0 C16 C15 H15 120.0 C11 C16 C15 120.3(2) C11 C16 H16 119.8 C15 C16 H16 119.8 C46 N41 C42 116.0(2) N41 C42 N43 126.0(2) N41 C42 N4 116.7(2) N43 C42 N4 117.3(2) C44 N43 C42 115.3(2) N43 C44 C45 123.8(2) N43 C44 H44 118.1 C45 C44 H44 118.1 C44 C45 C46 115.8(2) C44 C45 H45 122.1 C46 C45 H45 122.1 N41 C46 C45 123.1(2) N41 C46 H46 118.5 C45 C46 H46 118.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance N1 C17 1.346(3) N1 C2 1.461(3) N1 C6 1.464(3) C2 C3 1.521(4) C2 H2A 0.9900 C2 H2B 0.9900 C3 N4 1.459(3) C3 H3A 0.9900 C3 H3B 0.9900 N4 C42 1.379(3) N4 C5 1.468(3) C5 C6 1.521(3) C5 H5A 0.9900 C5 H5B 0.9900 C6 H6A 0.9900 C6 H6B 0.9900 C17 O17 1.226(3) C17 C11 1.513(3) C11 C16 1.390(3) C11 C12 1.394(3) C12 C13 1.393(3) C12 I12 2.104(2) C13 C14 1.388(4) C13 H13 0.9500 C14 C15 1.379(4) C14 H14 0.9500 C15 C16 1.391(3) C15 H15 0.9500 C16 H16 0.9500 N41 C46 1.339(3) N41 C42 1.344(3) C42 N43 1.344(3) N43 C44 1.340(3) C44 C45 1.375(4) C44 H44 0.9500 C45 C46 1.380(4) C45 H45 0.9500 C46 H46 0.9500 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag C13 H13 O17 2_545 0.95 2.40 3.160(3) 136 no C16 H16 O17 3_666 0.95 2.50 3.395(3) 157 y C45 H45 O17 1_556 0.95 2.57 3.508(3) 169 y C46 H46 Cg1 2_556 0.95 2.72 3.596(3) 153 y 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 C17 N1 C2 C3 116.2(3) C6 N1 C2 C3 -56.4(3) N1 C2 C3 N4 54.1(3) C2 C3 N4 C42 151.8(2) C2 C3 N4 C5 -56.4(3) C42 N4 C5 C6 -150.6(2) C3 N4 C5 C6 57.3(3) C17 N1 C6 C5 -116.3(2) C2 N1 C6 C5 56.8(3) N4 C5 C6 N1 -55.3(2) C2 N1 C17 O17 -173.7(3) C6 N1 C17 O17 -1.6(4) C2 N1 C17 C11 6.0(4) C6 N1 C17 C11 178.1(2) O17 C17 C11 C16 94.4(3) N1 C17 C11 C16 -85.3(3) O17 C17 C11 C12 -78.9(3) N1 C17 C11 C12 101.4(3) C16 C11 C12 C13 0.2(3) C17 C11 C12 C13 173.52(19) C16 C11 C12 I12 179.44(16) C17 C11 C12 I12 -7.2(3) C11 C12 C13 C14 -0.6(3) I12 C12 C13 C14 -179.83(16) C12 C13 C14 C15 0.6(3) C13 C14 C15 C16 -0.3(4) C12 C11 C16 C15 0.1(3) C17 C11 C16 C15 -173.4(2) C14 C15 C16 C11 -0.1(4) C46 N41 C42 N43 -1.0(4) C46 N41 C42 N4 177.6(2) C3 N4 C42 N41 175.3(2) C5 N4 C42 N41 25.3(3) C3 N4 C42 N43 -6.0(3) C5 N4 C42 N43 -156.1(2) N41 C42 N43 C44 1.1(4) N4 C42 N43 C44 -177.5(2) C42 N43 C44 C45 -0.7(4) N43 C44 C45 C46 0.4(4) C42 N41 C46 C45 0.5(4) C44 C45 C46 N41 -0.3(4) _cod_database_fobs_code 2242817