#------------------------------------------------------------------------------ #$Date: 2018-08-11 03:49:28 +0300 (Sat, 11 Aug 2018) $ #$Revision: 209556 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/05/76/7057640.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_7057640 loop_ _publ_author_name 'Sonawane, Amol D.' 'GARUD, DINESH RAMESH' 'Udagawa, Taro' 'Kubota, Yasuhiro' 'Koketsu, Mamoru' _publ_section_title ; Synthesis of thieno[2,3-c]acridine and furo[2,3-c]acridine derivatives via iodocyclization reaction, fluorescence properties and DFT mechanistic study ; _journal_name_full 'New Journal of Chemistry' _journal_paper_doi 10.1039/C8NJ03511C _journal_year 2018 _chemical_formula_sum 'C22 H14 I N S' _chemical_formula_weight 451.30 _space_group_crystal_system orthorhombic _space_group_IT_number 61 _space_group_name_Hall '-P 2ac 2ab' _space_group_name_H-M_alt 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M 'P b c a' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2017/1 _audit_update_record ; 2018-08-08 deposited with the CCDC. 2018-08-10 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 9.935(6) _cell_length_b 20.797(12) _cell_length_c 17.5203(10) _cell_measurement_reflns_used 7279 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 31.0 _cell_measurement_theta_min 3.3 _cell_volume 3620(3) _computing_cell_refinement CRYSTALCLEAR _computing_data_collection CRYSTALCLEAR _computing_data_reduction CRYSTALCLEAR _computing_molecular_graphics 'Yadokari-XG 2009 (Wakita, Nemoto et al., 2009)' _computing_publication_material 'Yadokari-XG 2009 (Wakita, Nemoto et al., 2009)' _computing_structure_refinement 'SHELXL-2017/1 (Sheldrick, 2017)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 296(2) _diffrn_detector_area_resol_mean 14.6199 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Rigaku/MSC Mercury CCD' _diffrn_measurement_method dtprofit.ref _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71075 _diffrn_reflns_av_R_equivalents 0.0530 _diffrn_reflns_av_unetI/netI 0.0358 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 31359 _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 27.500 _diffrn_reflns_theta_min 3.100 _diffrn_source 'Rotating Anode' _exptl_absorpt_coefficient_mu 1.888 _exptl_absorpt_correction_T_max 0.950 _exptl_absorpt_correction_T_min 0.813 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'REQAB (Rigaku, 1998)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.656 _exptl_crystal_description rod _exptl_crystal_F_000 1776 _exptl_crystal_size_max 1.000 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.100 _refine_diff_density_max 0.677 _refine_diff_density_min -0.607 _refine_diff_density_rms 0.074 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 227 _refine_ls_number_reflns 4148 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.045 _refine_ls_R_factor_all 0.0744 _refine_ls_R_factor_gt 0.0497 _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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1489 _refine_ls_wR_factor_ref 0.1688 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3027 _reflns_number_total 4148 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c8nj03511c3.cif _cod_data_source_block 180124 _cod_database_code 7057640 _shelx_shelxl_version_number 2017/1 _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 0.254 _shelx_estimated_absorpt_t_max 0.834 _shelx_res_file ; TITL 180124_a.res in Pbca 180124.res created by SHELXL-2017/1 at 14:18:54 on 08-Aug-2018 REM Yadorkari-X generated CELL 0.71075 9.9350 20.7970 17.5203 90.0000 90.0000 90.0000 ZERR 8.0 0.0060 0.0120 0.0010 0.0000 0.0000 0.0000 LATT 1 SYMM 1/2-X, -Y, 1/2+Z SYMM 1/2+X, 1/2-Y, -Z SYMM -X, 1/2+Y, 1/2-Z REM SPGR Pbca orthorhombic SFAC C H I N S UNIT 176 112 8 8 8 SIZE 1.00 0.10 0.10 TEMP 23.0 L.S. 10 FMAP 2 PLAN -1 ACTA CONF LIST 4 BOND $H MERG 2 OMIT -10.000000 55.000000 WGHT 0.100000 FVAR 0.80705 I2 3 0.484751 0.710851 0.512121 11.00000 0.07622 0.07456 = 0.03773 0.00595 -0.00046 0.00951 S3 5 0.746290 0.588225 0.768742 11.00000 0.05001 0.04803 = 0.06419 0.00968 -0.00086 0.00981 N4 4 0.407110 0.757683 0.819889 11.00000 0.04451 0.05064 = 0.03871 0.00458 -0.00305 0.00249 C10 1 0.471004 0.725298 0.764334 11.00000 0.03816 0.04080 = 0.04176 0.00402 0.00227 -0.00108 C11 1 0.446701 0.734842 0.684692 11.00000 0.04580 0.04395 = 0.03868 0.00745 -0.00221 -0.00241 C12 1 0.518332 0.695794 0.629567 11.00000 0.05090 0.04851 = 0.03135 0.00382 0.00173 0.00021 C13 1 0.570063 0.678279 0.786649 11.00000 0.03883 0.04382 = 0.04645 0.00754 -0.00428 -0.00433 C14 1 0.633058 0.642322 0.729975 11.00000 0.03781 0.03960 = 0.04798 0.00576 0.00348 -0.00091 C15 1 0.608903 0.649391 0.650589 11.00000 0.04359 0.04500 = 0.04310 0.00498 0.00666 -0.00405 C16 1 0.313427 0.801700 0.797607 11.00000 0.04009 0.04249 = 0.05365 -0.00033 0.00149 -0.00472 C17 1 0.282800 0.814958 0.720993 11.00000 0.04023 0.04958 = 0.05527 0.00720 -0.00300 -0.00236 C18 1 0.681942 0.607780 0.595654 11.00000 0.05191 0.04787 = 0.04739 0.00171 -0.00004 0.00012 C19 1 0.617787 0.661793 0.860892 11.00000 0.05489 0.05923 = 0.04657 0.00982 -0.00464 0.00576 AFIX 43 H1 2 0.587548 0.681399 0.905412 11.00000 -1.20000 AFIX 0 C20 1 0.351858 0.780249 0.664578 11.00000 0.05102 0.05705 = 0.03569 0.00995 -0.00739 -0.00015 AFIX 43 H2 2 0.333594 0.787895 0.613314 11.00000 -1.20000 AFIX 0 C21 1 0.710896 0.615030 0.859811 11.00000 0.05755 0.06214 = 0.05080 0.01122 -0.00783 0.00091 AFIX 43 H3 2 0.751948 0.598807 0.903456 11.00000 -1.20000 AFIX 0 C22 1 0.119106 0.895536 0.758238 11.00000 0.04113 0.05033 = 0.09426 0.00258 -0.00270 0.00033 C23 1 0.242110 0.836798 0.855429 11.00000 0.05679 0.07308 = 0.05146 -0.00870 0.00511 0.01053 AFIX 43 H4 2 0.259002 0.828734 0.906754 11.00000 -1.20000 AFIX 0 C24 1 0.182844 0.862392 0.702610 11.00000 0.04536 0.05129 = 0.07213 0.01144 -0.00927 0.00128 AFIX 43 H5 2 0.161722 0.870396 0.651777 11.00000 -1.20000 AFIX 0 C25 1 0.800397 0.627075 0.562969 11.00000 0.05446 0.06992 = 0.08562 -0.02422 0.02291 -0.01218 AFIX 43 H6 2 0.836556 0.666720 0.576482 11.00000 -1.20000 AFIX 0 C26 1 0.150134 0.881699 0.834998 11.00000 0.04875 0.07186 = 0.08416 -0.01791 0.00977 0.00719 AFIX 43 H7 2 0.105628 0.904328 0.873197 11.00000 -1.20000 AFIX 0 C27 1 0.014074 0.946066 0.740162 11.00000 0.05567 0.05413 = 0.12782 0.00623 -0.00322 0.01351 AFIX 137 H8 2 0.002103 0.948782 0.685886 11.00000 -1.50000 H9 2 0.043260 0.986973 0.759414 11.00000 -1.50000 H10 2 -0.069719 0.934476 0.763726 11.00000 -1.50000 AFIX 0 C28 1 0.632820 0.547819 0.577250 11.00000 0.08559 0.06039 = 0.10012 -0.01333 0.03475 -0.01160 AFIX 43 H11 2 0.553795 0.532981 0.599595 11.00000 -1.20000 AFIX 0 C29 1 0.867565 0.589493 0.510667 11.00000 0.06539 0.10318 = 0.09689 -0.03459 0.02645 -0.00619 AFIX 43 H12 2 0.947335 0.603854 0.488737 11.00000 -1.20000 AFIX 0 C30 1 0.815502 0.530641 0.491275 11.00000 0.08533 0.08582 = 0.08378 -0.03255 0.01740 0.00792 AFIX 43 H13 2 0.858716 0.505503 0.454851 11.00000 -1.20000 AFIX 0 C31 1 0.702334 0.509120 0.524655 11.00000 0.11316 0.05494 = 0.12316 -0.03316 0.03178 -0.00625 AFIX 43 H14 2 0.669853 0.468372 0.512868 11.00000 -1.20000 AFIX 0 HKLF 4 1 1 0 0 0 0 1 0 -1 0 REM 180124_a.res in Pbca REM R1 = 0.0497 for 3027 Fo > 4sig(Fo) and 0.0744 for all 4148 data REM 227 parameters refined using 0 restraints END WGHT 0.0431 2.6648 REM Highest difference peak 0.677, deepest hole -0.607, 1-sigma level 0.074 Q1 1 0.9827 0.6308 0.4872 11.00000 0.05 0.42 ; _shelx_res_checksum 93076 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, 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 I2 I 0.48475(4) 0.71085(2) 0.51212(2) 0.06284(19) Uani 1 1 d . . S3 S 0.74629(12) 0.58822(6) 0.76874(8) 0.0541(3) Uani 1 1 d . . N4 N 0.4071(3) 0.75768(18) 0.8199(2) 0.0446(8) Uani 1 1 d . . C10 C 0.4710(4) 0.7253(2) 0.7643(3) 0.0402(9) Uani 1 1 d . . C11 C 0.4467(4) 0.7348(2) 0.6847(3) 0.0428(9) Uani 1 1 d . . C12 C 0.5183(4) 0.6958(2) 0.6296(3) 0.0436(10) Uani 1 1 d . . C13 C 0.5701(4) 0.6783(2) 0.7866(2) 0.0430(9) Uani 1 1 d . . C14 C 0.6331(4) 0.6423(2) 0.7300(3) 0.0418(9) Uani 1 1 d . . C15 C 0.6089(4) 0.6494(2) 0.6506(3) 0.0439(10) Uani 1 1 d . . C16 C 0.3134(4) 0.8017(2) 0.7976(3) 0.0454(10) Uani 1 1 d . . C17 C 0.2828(4) 0.8150(2) 0.7210(3) 0.0484(10) Uani 1 1 d . . C18 C 0.6819(5) 0.6078(2) 0.5957(3) 0.0491(10) Uani 1 1 d . . C19 C 0.6178(5) 0.6618(2) 0.8609(3) 0.0536(12) Uani 1 1 d . . H1 H 0.587548 0.681399 0.905412 0.064 Uiso 1 1 calc R U C20 C 0.3519(4) 0.7802(2) 0.6646(3) 0.0479(11) Uani 1 1 d . . H2 H 0.333594 0.787895 0.613314 0.058 Uiso 1 1 calc R U C21 C 0.7109(5) 0.6150(2) 0.8598(3) 0.0568(12) Uani 1 1 d . . H3 H 0.751948 0.598807 0.903456 0.068 Uiso 1 1 calc R U C22 C 0.1191(5) 0.8955(2) 0.7582(4) 0.0619(14) Uani 1 1 d . . C23 C 0.2421(5) 0.8368(3) 0.8554(3) 0.0604(13) Uani 1 1 d . . H4 H 0.259002 0.828734 0.906754 0.073 Uiso 1 1 calc R U C24 C 0.1828(4) 0.8624(2) 0.7026(3) 0.0563(12) Uani 1 1 d . . H5 H 0.161722 0.870396 0.651777 0.068 Uiso 1 1 calc R U C25 C 0.8004(5) 0.6271(3) 0.5630(4) 0.0700(15) Uani 1 1 d . . H6 H 0.836556 0.666720 0.576482 0.084 Uiso 1 1 calc R U C26 C 0.1501(5) 0.8817(3) 0.8350(4) 0.0683(15) Uani 1 1 d . . H7 H 0.105628 0.904328 0.873197 0.082 Uiso 1 1 calc R U C27 C 0.0141(5) 0.9461(3) 0.7402(5) 0.079(2) Uani 1 1 d . . H8 H 0.002103 0.948782 0.685886 0.119 Uiso 1 1 calc R U H9 H 0.043260 0.986973 0.759414 0.119 Uiso 1 1 calc R U H10 H -0.069719 0.934476 0.763726 0.119 Uiso 1 1 calc R U C28 C 0.6328(6) 0.5478(3) 0.5773(4) 0.0820(18) Uani 1 1 d . . H11 H 0.553795 0.532981 0.599595 0.098 Uiso 1 1 calc R U C29 C 0.8676(7) 0.5895(4) 0.5107(4) 0.088(2) Uani 1 1 d . . H12 H 0.947335 0.603854 0.488737 0.106 Uiso 1 1 calc R U C30 C 0.8155(8) 0.5306(4) 0.4913(4) 0.0850(19) Uani 1 1 d . . H13 H 0.858716 0.505503 0.454851 0.102 Uiso 1 1 calc R U C31 C 0.7023(9) 0.5091(3) 0.5247(5) 0.097(2) Uani 1 1 d . . H14 H 0.669853 0.468372 0.512868 0.117 Uiso 1 1 calc R U 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 I2 0.0762(3) 0.0746(3) 0.0377(3) 0.00595(15) -0.00046(14) 0.00951(17) S3 0.0500(6) 0.0480(7) 0.0642(8) 0.0097(6) -0.0009(5) 0.0098(5) N4 0.0445(18) 0.051(2) 0.0387(19) 0.0046(16) -0.0030(15) 0.0025(17) C10 0.038(2) 0.041(2) 0.042(3) 0.0040(18) 0.0023(17) -0.0011(17) C11 0.046(2) 0.044(2) 0.039(2) 0.0075(19) -0.0022(19) -0.0024(19) C12 0.051(2) 0.049(2) 0.031(2) 0.0038(19) 0.0017(17) 0.0002(19) C13 0.039(2) 0.044(2) 0.046(2) 0.0075(19) -0.0043(18) -0.0043(18) C14 0.0378(19) 0.040(2) 0.048(2) 0.0058(19) 0.0035(17) -0.0009(17) C15 0.044(2) 0.045(2) 0.043(2) 0.0050(19) 0.0067(18) -0.0041(18) C16 0.040(2) 0.042(2) 0.054(3) 0.000(2) 0.0015(19) -0.0047(18) C17 0.040(2) 0.050(3) 0.055(3) 0.007(2) -0.0030(19) -0.0024(19) C18 0.052(2) 0.048(3) 0.047(3) 0.002(2) 0.000(2) 0.000(2) C19 0.055(3) 0.059(3) 0.047(3) 0.010(2) -0.005(2) 0.006(2) C20 0.051(2) 0.057(3) 0.036(2) 0.0100(19) -0.0074(19) 0.000(2) C21 0.058(3) 0.062(3) 0.051(3) 0.011(2) -0.008(2) 0.001(2) C22 0.041(2) 0.050(3) 0.094(4) 0.003(3) -0.003(3) 0.000(2) C23 0.057(3) 0.073(3) 0.051(3) -0.009(2) 0.005(2) 0.011(3) C24 0.045(2) 0.051(3) 0.072(3) 0.011(3) -0.009(2) 0.001(2) C25 0.054(3) 0.070(3) 0.086(4) -0.024(3) 0.023(3) -0.012(2) C26 0.049(3) 0.072(4) 0.084(4) -0.018(3) 0.010(3) 0.007(3) C27 0.056(3) 0.054(3) 0.128(7) 0.006(4) -0.003(3) 0.014(2) C28 0.086(4) 0.060(3) 0.100(5) -0.013(3) 0.035(4) -0.012(3) C29 0.065(4) 0.103(5) 0.097(5) -0.035(4) 0.026(3) -0.006(4) C30 0.085(5) 0.086(5) 0.084(4) -0.033(3) 0.017(3) 0.008(4) C31 0.113(6) 0.055(4) 0.123(6) -0.033(4) 0.032(5) -0.006(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' 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' S S 0.1246 0.1234 '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 C21 S3 C14 91.2(2) C10 N4 C16 116.9(4) N4 C10 C11 123.9(4) N4 C10 C13 117.8(4) C11 C10 C13 118.3(4) C20 C11 C10 117.4(4) C20 C11 C12 123.3(4) C10 C11 C12 119.3(4) C15 C12 C11 122.6(4) C15 C12 I2 118.1(3) C11 C12 I2 119.3(3) C14 C13 C19 111.8(4) C14 C13 C10 118.6(4) C19 C13 C10 129.6(4) C13 C14 C15 124.6(4) C13 C14 S3 111.2(3) C15 C14 S3 124.2(3) C12 C15 C14 116.6(4) C12 C15 C18 123.9(4) C14 C15 C18 119.5(4) N4 C16 C17 123.6(4) N4 C16 C23 118.5(4) C17 C16 C23 117.9(4) C20 C17 C16 117.8(4) C20 C17 C24 122.2(5) C16 C17 C24 119.9(5) C25 C18 C28 118.2(5) C25 C18 C15 121.4(4) C28 C18 C15 120.4(4) C21 C19 C13 113.0(5) C21 C19 H1 123.5 C13 C19 H1 123.5 C11 C20 C17 120.4(4) C11 C20 H2 119.8 C17 C20 H2 119.8 C19 C21 S3 112.8(4) C19 C21 H3 123.6 S3 C21 H3 123.6 C24 C22 C26 118.8(5) C24 C22 C27 121.7(6) C26 C22 C27 119.5(6) C26 C23 C16 119.8(5) C26 C23 H4 120.1 C16 C23 H4 120.1 C22 C24 C17 120.8(5) C22 C24 H5 119.6 C17 C24 H5 119.6 C18 C25 C29 121.9(5) C18 C25 H6 119.0 C29 C25 H6 119.0 C23 C26 C22 122.7(5) C23 C26 H7 118.6 C22 C26 H7 118.6 C22 C27 H8 109.5 C22 C27 H9 109.5 H8 C27 H9 109.5 C22 C27 H10 109.5 H8 C27 H10 109.5 H9 C27 H10 109.5 C18 C28 C31 119.9(6) C18 C28 H11 120.1 C31 C28 H11 120.1 C30 C29 C25 119.3(6) C30 C29 H12 120.4 C25 C29 H12 120.4 C31 C30 C29 120.3(6) C31 C30 H13 119.8 C29 C30 H13 119.8 C30 C31 C28 120.4(6) C30 C31 H14 119.8 C28 C31 H14 119.8 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance I2 C12 2.108(5) S3 C21 1.726(5) S3 C14 1.730(4) N4 C10 1.343(6) N4 C16 1.363(6) C10 C11 1.430(7) C10 C13 1.441(6) C11 C20 1.380(6) C11 C12 1.449(7) C12 C15 1.370(6) C13 C14 1.392(6) C13 C19 1.426(6) C14 C15 1.419(6) C15 C18 1.484(6) C16 C17 1.404(7) C16 C23 1.436(6) C17 C20 1.403(7) C17 C24 1.436(6) C18 C25 1.369(6) C18 C28 1.377(7) C19 C21 1.342(7) C19 H1 0.9300 C20 H2 0.9300 C21 H3 0.9300 C22 C24 1.351(7) C22 C26 1.409(8) C22 C27 1.514(7) C23 C26 1.355(7) C23 H4 0.9300 C24 H5 0.9300 C25 C29 1.377(8) C25 H6 0.9300 C26 H7 0.9300 C27 H8 0.9600 C27 H9 0.9600 C27 H10 0.9600 C28 C31 1.405(8) C28 H11 0.9300 C29 C30 1.371(10) C29 H12 0.9300 C30 C31 1.344(11) C30 H13 0.9300 C31 H14 0.9300 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 C16 N4 C10 C11 0.4(6) C16 N4 C10 C13 -179.7(4) N4 C10 C11 C20 0.1(6) C13 C10 C11 C20 -179.8(4) N4 C10 C11 C12 -178.1(4) C13 C10 C11 C12 2.1(6) C20 C11 C12 C15 -177.7(4) C10 C11 C12 C15 0.3(7) C20 C11 C12 I2 2.9(6) C10 C11 C12 I2 -179.1(3) N4 C10 C13 C14 177.3(4) C11 C10 C13 C14 -2.9(6) N4 C10 C13 C19 -3.3(7) C11 C10 C13 C19 176.6(4) C19 C13 C14 C15 -178.2(4) C10 C13 C14 C15 1.4(6) C19 C13 C14 S3 1.2(5) C10 C13 C14 S3 -179.2(3) C21 S3 C14 C13 -1.0(3) C21 S3 C14 C15 178.4(4) C11 C12 C15 C14 -1.8(6) I2 C12 C15 C14 177.5(3) C11 C12 C15 C18 178.8(4) I2 C12 C15 C18 -1.8(6) C13 C14 C15 C12 1.0(6) S3 C14 C15 C12 -178.3(3) C13 C14 C15 C18 -179.6(4) S3 C14 C15 C18 1.1(6) C10 N4 C16 C17 -0.9(6) C10 N4 C16 C23 179.4(4) N4 C16 C17 C20 0.7(7) C23 C16 C17 C20 -179.5(4) N4 C16 C17 C24 -179.7(4) C23 C16 C17 C24 0.0(6) C12 C15 C18 C25 86.4(6) C14 C15 C18 C25 -93.0(6) C12 C15 C18 C28 -94.8(6) C14 C15 C18 C28 85.9(6) C14 C13 C19 C21 -0.8(6) C10 C13 C19 C21 179.7(5) C10 C11 C20 C17 -0.2(6) C12 C11 C20 C17 177.8(4) C16 C17 C20 C11 -0.1(7) C24 C17 C20 C11 -179.7(4) C13 C19 C21 S3 0.0(6) C14 S3 C21 C19 0.6(4) N4 C16 C23 C26 178.8(4) C17 C16 C23 C26 -1.0(7) C26 C22 C24 C17 -1.5(7) C27 C22 C24 C17 179.6(4) C20 C17 C24 C22 -179.3(4) C16 C17 C24 C22 1.2(7) C28 C18 C25 C29 2.6(10) C15 C18 C25 C29 -178.6(6) C16 C23 C26 C22 0.7(8) C24 C22 C26 C23 0.5(8) C27 C22 C26 C23 179.5(5) C25 C18 C28 C31 -1.7(10) C15 C18 C28 C31 179.5(6) C18 C25 C29 C30 -0.8(11) C25 C29 C30 C31 -2.0(13) C29 C30 C31 C28 2.8(14) C18 C28 C31 C30 -1.0(13)