_audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'deprotonated 1,3-bis(3-nitrophenyl)thiourea' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H29 N5 O4 S1' _chemical_formula_weight 447.56 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' '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' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_H-M 'P21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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' _cell_length_a 8.548(6) _cell_length_b 20.740(14) _cell_length_c 12.667(10) _cell_angle_alpha 90.00 _cell_angle_beta 101.513(15) _cell_angle_gamma 90.00 _cell_volume 2201(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.8 _cell_measurement_theta_max 31.3 _exptl_crystal_description 'block' _exptl_crystal_colour 'orange' _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.351 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 952 _exptl_absorpt_coefficient_mu 0.185 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.489 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ; Jacobson, R. (1998). REQAB. Private communication to the Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9541 _diffrn_reflns_av_R_equivalents 0.0487 _diffrn_reflns_av_sigmaI/netI 0.0912 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4897 _reflns_number_gt 3507 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0460P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0017(8) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 4897 _refine_ls_number_parameters 285 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0806 _refine_ls_R_factor_gt 0.0554 _refine_ls_wR_factor_ref 0.1270 _refine_ls_wR_factor_gt 0.1123 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O5 O -0.31976(18) 0.19365(8) 0.92524(14) 0.0273(4) Uani 1 1 d . . . O4 O 0.2448(2) 0.35252(9) 0.45896(15) 0.0364(5) Uani 1 1 d . . . O6 O -0.3225(2) 0.14800(8) 1.07870(14) 0.0314(5) Uani 1 1 d . . . O3 O 0.0189(2) 0.37748(9) 0.50009(15) 0.0375(5) Uani 1 1 d . . . C36 C 0.4712(3) 0.45625(11) 1.1388(2) 0.0240(6) Uani 1 1 d . . . H36A H 0.3892 0.4736 1.0792 0.029 Uiso 1 1 calc R . . H36B H 0.5763 0.4719 1.1279 0.029 Uiso 1 1 calc R . . C31 C 0.7291(3) 0.46437(12) 1.3452(2) 0.0277(6) Uani 1 1 d . . . H31A H 0.7906 0.4446 1.4107 0.041 Uiso 1 1 calc R . . H31B H 0.7541 0.5105 1.3447 0.041 Uiso 1 1 calc R . . H31C H 0.7570 0.4437 1.2819 0.041 Uiso 1 1 calc R . . C37 C 0.4695(3) 0.38356(12) 1.1305(2) 0.0336(7) Uani 1 1 d . . . H37A H 0.4897 0.3708 1.0599 0.050 Uiso 1 1 calc R . . H37B H 0.3650 0.3672 1.1387 0.050 Uiso 1 1 calc R . . H37C H 0.5527 0.3656 1.1874 0.050 Uiso 1 1 calc R . . C34 C 0.2709(3) 0.46868(11) 1.2529(2) 0.0254(6) Uani 1 1 d . . . H34A H 0.2598 0.4212 1.2563 0.031 Uiso 1 1 calc R . . H34B H 0.1990 0.4836 1.1863 0.031 Uiso 1 1 calc R . . C35 C 0.2152(3) 0.49802(12) 1.3487(2) 0.0294(6) Uani 1 1 d . . . H35A H 0.1046 0.4851 1.3474 0.044 Uiso 1 1 calc R . . H35B H 0.2214 0.5451 1.3450 0.044 Uiso 1 1 calc R . . H35C H 0.2836 0.4828 1.4155 0.044 Uiso 1 1 calc R . . C33 C 0.3473(3) 0.59291(12) 1.1603(2) 0.0322(6) Uani 1 1 d . . . H33A H 0.3734 0.6390 1.1643 0.048 Uiso 1 1 calc R . . H33B H 0.2405 0.5865 1.1756 0.048 Uiso 1 1 calc R . . H33C H 0.3497 0.5768 1.0878 0.048 Uiso 1 1 calc R . . C32 C 0.4691(3) 0.55631(11) 1.2426(2) 0.0238(6) Uani 1 1 d . . . H32A H 0.5767 0.5641 1.2273 0.029 Uiso 1 1 calc R . . H32B H 0.4680 0.5739 1.3151 0.029 Uiso 1 1 calc R . . C30 C 0.5528(3) 0.45573(12) 1.3425(2) 0.0253(6) Uani 1 1 d . . . H30A H 0.5275 0.4757 1.4080 0.030 Uiso 1 1 calc R . . H30B H 0.5304 0.4090 1.3455 0.030 Uiso 1 1 calc R . . H4A H -0.015(3) 0.4327(12) 1.040(2) 0.025(7) Uiso 1 1 d . . . S1 S 0.13722(7) 0.46450(3) 0.88663(5) 0.02290(18) Uani 1 1 d . . . N4 N -0.0007(2) 0.39717(10) 1.01933(17) 0.0219(5) Uani 1 1 d . . . N5 N 0.1014(2) 0.33364(9) 0.90200(16) 0.0226(5) Uani 1 1 d . . . N2 N 0.1546(2) 0.35480(10) 0.52354(18) 0.0271(5) Uani 1 1 d . . . N3 N 0.4412(2) 0.48414(9) 1.24445(16) 0.0209(5) Uani 1 1 d . . . N1 N -0.2854(2) 0.19260(9) 1.02476(18) 0.0223(5) Uani 1 1 d . . . C2 C -0.0623(2) 0.34723(11) 1.07361(19) 0.0189(5) Uani 1 1 d . . . C5 C -0.1876(3) 0.25280(11) 1.1920(2) 0.0228(5) Uani 1 1 d . . . H5 H -0.2286 0.2199 1.2311 0.027 Uiso 1 1 calc R . . C8 C 0.1817(3) 0.32288(11) 0.8173(2) 0.0210(5) Uani 1 1 d . . . C13 C 0.1291(3) 0.34668(11) 0.7129(2) 0.0213(5) Uani 1 1 d . . . H13 H 0.0386 0.3742 0.6971 0.026 Uiso 1 1 calc R . . C1 C 0.0774(3) 0.39157(11) 0.93351(19) 0.0205(5) Uani 1 1 d . . . C10 C 0.3939(3) 0.26640(12) 0.7544(2) 0.0264(6) Uani 1 1 d . . . H10 H 0.4846 0.2389 0.7695 0.032 Uiso 1 1 calc R . . C7 C -0.1375(2) 0.29331(11) 1.0206(2) 0.0200(5) Uani 1 1 d . . . H7 H -0.1460 0.2877 0.9453 0.024 Uiso 1 1 calc R . . C3 C -0.0546(3) 0.35362(11) 1.18441(19) 0.0226(5) Uani 1 1 d . . . H3 H -0.0071 0.3911 1.2202 0.027 Uiso 1 1 calc R . . C6 C -0.1994(2) 0.24826(11) 1.08155(19) 0.0200(5) Uani 1 1 d . . . C9 C 0.3140(3) 0.28185(11) 0.8363(2) 0.0239(5) Uani 1 1 d . . . H9 H 0.3498 0.2643 0.9062 0.029 Uiso 1 1 calc R . . C4 C -0.1143(3) 0.30679(12) 1.2432(2) 0.0256(6) Uani 1 1 d . . . H4 H -0.1049 0.3118 1.3187 0.031 Uiso 1 1 calc R . . C12 C 0.2103(3) 0.32975(11) 0.6331(2) 0.0218(5) Uani 1 1 d . . . C11 C 0.3435(3) 0.29044(12) 0.6510(2) 0.0258(6) Uani 1 1 d . . . H11 H 0.3983 0.2803 0.5948 0.031 Uiso 1 1 calc R . . 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 O5 0.0357(9) 0.0290(9) 0.0178(11) -0.0037(8) 0.0067(8) -0.0048(8) O4 0.0502(11) 0.0421(11) 0.0217(12) 0.0049(9) 0.0184(9) 0.0081(9) O6 0.0427(10) 0.0245(9) 0.0313(12) 0.0069(8) 0.0176(9) -0.0049(8) O3 0.0347(10) 0.0490(12) 0.0275(12) 0.0049(9) 0.0030(8) 0.0121(9) C36 0.0294(13) 0.0251(12) 0.0193(15) -0.0010(11) 0.0087(10) -0.0006(10) C31 0.0275(13) 0.0313(14) 0.0241(16) 0.0049(12) 0.0049(11) 0.0029(11) C37 0.0404(15) 0.0250(13) 0.0387(19) -0.0063(13) 0.0153(13) 0.0028(12) C34 0.0229(12) 0.0253(12) 0.0296(16) -0.0017(11) 0.0089(11) -0.0008(10) C35 0.0268(13) 0.0330(14) 0.0311(17) -0.0047(12) 0.0119(11) -0.0050(11) C33 0.0341(14) 0.0252(13) 0.0364(18) 0.0075(12) 0.0049(12) 0.0072(11) C32 0.0263(12) 0.0213(12) 0.0245(15) -0.0024(11) 0.0070(10) -0.0013(10) C30 0.0289(13) 0.0296(13) 0.0177(15) 0.0050(11) 0.0054(10) 0.0020(11) S1 0.0284(3) 0.0217(3) 0.0211(4) 0.0002(3) 0.0111(3) -0.0030(2) N4 0.0323(11) 0.0191(10) 0.0172(12) -0.0022(9) 0.0120(9) -0.0027(9) N5 0.0300(11) 0.0209(10) 0.0204(12) 0.0002(9) 0.0132(9) 0.0004(9) N2 0.0333(12) 0.0268(11) 0.0223(13) -0.0020(10) 0.0085(10) 0.0009(10) N3 0.0220(10) 0.0232(10) 0.0183(12) 0.0005(9) 0.0060(8) -0.0004(8) N1 0.0248(10) 0.0211(10) 0.0236(13) 0.0021(9) 0.0109(9) 0.0008(9) C2 0.0193(11) 0.0229(11) 0.0160(13) -0.0002(10) 0.0073(9) 0.0030(10) C5 0.0286(12) 0.0233(12) 0.0197(15) 0.0038(11) 0.0126(11) 0.0021(10) C8 0.0254(12) 0.0210(11) 0.0190(15) -0.0027(10) 0.0106(10) -0.0069(10) C13 0.0241(12) 0.0195(11) 0.0219(15) -0.0019(10) 0.0081(10) -0.0014(10) C1 0.0218(11) 0.0258(12) 0.0146(14) 0.0001(10) 0.0051(10) -0.0002(10) C10 0.0274(13) 0.0293(13) 0.0228(15) -0.0019(11) 0.0057(11) 0.0043(11) C7 0.0230(11) 0.0242(12) 0.0147(13) 0.0016(10) 0.0084(10) 0.0021(10) C3 0.0234(12) 0.0274(12) 0.0185(15) -0.0043(11) 0.0075(10) -0.0022(10) C6 0.0216(12) 0.0205(11) 0.0191(15) -0.0002(10) 0.0070(10) 0.0022(10) C9 0.0276(12) 0.0260(12) 0.0190(15) 0.0006(11) 0.0067(10) -0.0001(11) C4 0.0311(13) 0.0327(13) 0.0160(15) -0.0001(11) 0.0114(11) 0.0016(11) C12 0.0257(12) 0.0257(12) 0.0148(14) 0.0010(10) 0.0058(10) -0.0035(10) C11 0.0262(12) 0.0315(14) 0.0220(15) -0.0055(12) 0.0102(11) -0.0004(11) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; 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 O5 N1 1.236(3) . ? O4 N2 1.233(2) . ? O6 N1 1.228(2) . ? O3 N2 1.231(2) . ? C36 C37 1.511(3) . ? C36 N3 1.526(3) . ? C36 H36A 0.9900 . ? C36 H36B 0.9900 . ? C31 C30 1.512(3) . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? C34 N3 1.515(3) . ? C34 C35 1.517(3) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? C33 C32 1.521(3) . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C32 N3 1.517(3) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C30 N3 1.525(3) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? S1 C1 1.739(3) . ? N4 C1 1.390(3) . ? N4 C2 1.403(3) . ? N4 H4A 0.80(2) . ? N5 C1 1.295(3) . ? N5 C8 1.402(3) . ? N2 C12 1.469(3) . ? N1 C6 1.476(3) . ? C2 C7 1.394(3) . ? C2 C3 1.398(3) . ? C5 C4 1.380(3) . ? C5 C6 1.386(3) . ? C5 H5 0.9500 . ? C8 C9 1.397(3) . ? C8 C13 1.399(3) . ? C13 C12 1.381(3) . ? C13 H13 0.9500 . ? C10 C11 1.388(3) . ? C10 C9 1.388(3) . ? C10 H10 0.9500 . ? C7 C6 1.382(3) . ? C7 H7 0.9500 . ? C3 C4 1.382(3) . ? C3 H3 0.9500 . ? C9 H9 0.9500 . ? C4 H4 0.9500 . ? C12 C11 1.382(3) . ? C11 H11 0.9500 . ? 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 C37 C36 N3 116.0(2) . . ? C37 C36 H36A 108.3 . . ? N3 C36 H36A 108.3 . . ? C37 C36 H36B 108.3 . . ? N3 C36 H36B 108.3 . . ? H36A C36 H36B 107.4 . . ? C30 C31 H31A 109.5 . . ? C30 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C30 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C36 C37 H37A 109.5 . . ? C36 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C36 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? N3 C34 C35 115.5(2) . . ? N3 C34 H34A 108.4 . . ? C35 C34 H34A 108.4 . . ? N3 C34 H34B 108.4 . . ? C35 C34 H34B 108.4 . . ? H34A C34 H34B 107.5 . . ? C34 C35 H35A 109.5 . . ? C34 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C34 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? N3 C32 C33 114.52(19) . . ? N3 C32 H32A 108.6 . . ? C33 C32 H32A 108.6 . . ? N3 C32 H32B 108.6 . . ? C33 C32 H32B 108.6 . . ? H32A C32 H32B 107.6 . . ? C31 C30 N3 115.6(2) . . ? C31 C30 H30A 108.4 . . ? N3 C30 H30A 108.4 . . ? C31 C30 H30B 108.4 . . ? N3 C30 H30B 108.4 . . ? H30A C30 H30B 107.5 . . ? C1 N4 C2 127.4(2) . . ? C1 N4 H4A 117.5(18) . . ? C2 N4 H4A 115.0(18) . . ? C1 N5 C8 120.99(19) . . ? O3 N2 O4 122.6(2) . . ? O3 N2 C12 118.4(2) . . ? O4 N2 C12 119.0(2) . . ? C34 N3 C32 111.48(17) . . ? C34 N3 C30 108.33(18) . . ? C32 N3 C30 108.61(18) . . ? C34 N3 C36 108.29(18) . . ? C32 N3 C36 107.83(17) . . ? C30 N3 C36 112.35(18) . . ? O6 N1 O5 123.1(2) . . ? O6 N1 C6 118.4(2) . . ? O5 N1 C6 118.48(19) . . ? C7 C2 C3 118.9(2) . . ? C7 C2 N4 122.6(2) . . ? C3 C2 N4 118.4(2) . . ? C4 C5 C6 117.6(2) . . ? C4 C5 H5 121.2 . . ? C6 C5 H5 121.2 . . ? C9 C8 N5 117.9(2) . . ? C9 C8 C13 118.3(2) . . ? N5 C8 C13 123.6(2) . . ? C12 C13 C8 119.3(2) . . ? C12 C13 H13 120.4 . . ? C8 C13 H13 120.4 . . ? N5 C1 N4 116.7(2) . . ? N5 C1 S1 128.79(18) . . ? N4 C1 S1 114.49(17) . . ? C11 C10 C9 121.1(2) . . ? C11 C10 H10 119.5 . . ? C9 C10 H10 119.5 . . ? C6 C7 C2 117.7(2) . . ? C6 C7 H7 121.2 . . ? C2 C7 H7 121.2 . . ? C4 C3 C2 121.7(2) . . ? C4 C3 H3 119.1 . . ? C2 C3 H3 119.1 . . ? C7 C6 C5 124.0(2) . . ? C7 C6 N1 117.7(2) . . ? C5 C6 N1 118.3(2) . . ? C10 C9 C8 120.9(2) . . ? C10 C9 H9 119.5 . . ? C8 C9 H9 119.5 . . ? C5 C4 C3 120.0(2) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C11 C12 C13 123.2(2) . . ? C11 C12 N2 117.7(2) . . ? C13 C12 N2 119.1(2) . . ? C12 C11 C10 117.2(2) . . ? C12 C11 H11 121.4 . . ? C10 C11 H11 121.4 . . ? 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 C35 C34 N3 C32 -56.3(3) . . . . ? C35 C34 N3 C30 63.2(3) . . . . ? C35 C34 N3 C36 -174.7(2) . . . . ? C33 C32 N3 C34 -50.9(3) . . . . ? C33 C32 N3 C30 -170.23(19) . . . . ? C33 C32 N3 C36 67.8(2) . . . . ? C31 C30 N3 C34 177.7(2) . . . . ? C31 C30 N3 C32 -61.1(3) . . . . ? C31 C30 N3 C36 58.1(3) . . . . ? C37 C36 N3 C34 -66.5(3) . . . . ? C37 C36 N3 C32 172.7(2) . . . . ? C37 C36 N3 C30 53.1(3) . . . . ? C1 N4 C2 C7 -38.5(3) . . . . ? C1 N4 C2 C3 144.8(2) . . . . ? C1 N5 C8 C9 125.8(2) . . . . ? C1 N5 C8 C13 -59.6(3) . . . . ? C9 C8 C13 C12 -0.9(3) . . . . ? N5 C8 C13 C12 -175.5(2) . . . . ? C8 N5 C1 N4 -178.8(2) . . . . ? C8 N5 C1 S1 -1.8(4) . . . . ? C2 N4 C1 N5 -2.6(4) . . . . ? C2 N4 C1 S1 179.95(19) . . . . ? C3 C2 C7 C6 -0.8(3) . . . . ? N4 C2 C7 C6 -177.5(2) . . . . ? C7 C2 C3 C4 2.5(3) . . . . ? N4 C2 C3 C4 179.3(2) . . . . ? C2 C7 C6 C5 -1.6(3) . . . . ? C2 C7 C6 N1 177.33(18) . . . . ? C4 C5 C6 C7 2.3(3) . . . . ? C4 C5 C6 N1 -176.65(19) . . . . ? O6 N1 C6 C7 170.45(19) . . . . ? O5 N1 C6 C7 -11.0(3) . . . . ? O6 N1 C6 C5 -10.5(3) . . . . ? O5 N1 C6 C5 167.99(19) . . . . ? C11 C10 C9 C8 -0.9(4) . . . . ? N5 C8 C9 C10 176.6(2) . . . . ? C13 C8 C9 C10 1.7(3) . . . . ? C6 C5 C4 C3 -0.6(3) . . . . ? C2 C3 C4 C5 -1.8(3) . . . . ? C8 C13 C12 C11 -0.6(3) . . . . ? C8 C13 C12 N2 179.9(2) . . . . ? O3 N2 C12 C11 164.2(2) . . . . ? O4 N2 C12 C11 -16.0(3) . . . . ? O3 N2 C12 C13 -16.4(3) . . . . ? O4 N2 C12 C13 163.5(2) . . . . ? C13 C12 C11 C10 1.3(4) . . . . ? N2 C12 C11 C10 -179.2(2) . . . . ? C9 C10 C11 C12 -0.5(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N4 H4A S1 0.80(2) 2.63(2) 3.401(3) 164(2) 3_567 _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.260 _refine_diff_density_min -0.312 _refine_diff_density_rms 0.060