# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Chen-Jie Fang' _publ_contact_author_email CJFANG@CCMU.EDU.CN _publ_section_title ; An enhanced fluorescence in a tunable face-to-face pi-pi stacking assembly directed by the H-bonding ; loop_ _publ_author_name 'Chen-Jie Fang' 'Xiao-Fei Fu' 'Rui Guo' 'Le-Le Li' 'Wei Sun' 'Chun-Hu Xu' 'Chunhua Yan' 'Yan-Feng Yue' # Attachment 'B910263A.CIF' data_1 _database_code_depnum_ccdc_archive 'CCDC 721344' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H17 N3 S' _chemical_formula_weight 307.41 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' 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 P2(1)/n loop_ _symmetry_equiv_pos_as_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' _cell_length_a 20.622(4) _cell_length_b 7.3581(15) _cell_length_c 21.626(4) _cell_angle_alpha 90.00 _cell_angle_beta 103.42(3) _cell_angle_gamma 90.00 _cell_volume 3191.8(11) _cell_formula_units_Z 8 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 21988 _cell_measurement_theta_min 3.395 _cell_measurement_theta_max 27.485 _exptl_crystal_description rod-like _exptl_crystal_colour orange _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.279 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1296 _exptl_absorpt_coefficient_mu 0.203 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.891 _exptl_absorpt_correction_T_max 0.979 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'NONIUS KappaCCD Diffractometer' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 0.77 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 48641 _diffrn_reflns_av_R_equivalents 0.0660 _diffrn_reflns_av_sigmaI/netI 0.0615 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 3.40 _diffrn_reflns_theta_max 27.51 _reflns_number_total 7322 _reflns_number_gt 3675 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KappaCCD (Nonius B. V., 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL Denzo (Otwinowski & Minor, 1997) & maXus (Mackay et al., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL V5.1 (Sheldrick, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^ > 2sigma(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^)+(0.0521P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7322 _refine_ls_number_parameters 524 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1081 _refine_ls_R_factor_gt 0.0394 _refine_ls_wR_factor_ref 0.1016 _refine_ls_wR_factor_gt 0.0856 _refine_ls_goodness_of_fit_ref 0.905 _refine_ls_restrained_S_all 0.905 _refine_ls_shift/su_max 0.001 _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 C1 C 0.61793(13) 0.7258(4) 0.00862(11) 0.0810(6) Uani 1 1 d . . . H1A H 0.6547(10) 0.809(3) 0.0310(9) 0.096(7) Uiso 1 1 d . . . H1B H 0.6394(10) 0.596(3) 0.0061(9) 0.124(8) Uiso 1 1 d . . . H1C H 0.5994(10) 0.769(3) -0.0349(10) 0.107(7) Uiso 1 1 d . . . C2 C 0.56421(10) 0.7229(3) 0.04488(9) 0.0696(5) Uani 1 1 d . . . H2A H 0.5431(8) 0.841(2) 0.0471(7) 0.074(6) Uiso 1 1 d . . . H2B H 0.5299(8) 0.637(2) 0.0254(7) 0.066(5) Uiso 1 1 d . . . C3 C 0.55646(8) 0.6050(2) 0.15009(8) 0.0526(4) Uani 1 1 d . . . C4 C 0.68997(8) 0.5266(2) 0.27959(8) 0.0499(4) Uani 1 1 d . . . H4 H 0.6666(7) 0.4593(19) 0.3066(7) 0.057(5) Uiso 1 1 d . . . C5 C 0.76104(7) 0.55884(18) 0.30561(7) 0.0449(4) Uani 1 1 d . . . C6 C 0.80772(8) 0.55703(19) 0.26675(7) 0.0469(4) Uani 1 1 d . . . C7 C 0.79198(10) 0.5068(2) 0.20149(8) 0.0570(4) Uani 1 1 d . . . H7 H 0.7474(8) 0.4722(19) 0.1822(7) 0.052(5) Uiso 1 1 d . . . C8 C 0.83953(11) 0.5030(3) 0.16719(10) 0.0709(5) Uani 1 1 d . . . H8 H 0.8266(8) 0.467(2) 0.1224(9) 0.077(6) Uiso 1 1 d . . . C9 C 0.90580(12) 0.5522(3) 0.19495(12) 0.0794(6) Uani 1 1 d . . . H9 H 0.9373(10) 0.554(2) 0.1699(9) 0.094(7) Uiso 1 1 d . . . C10 C 0.92317(11) 0.6009(3) 0.25618(11) 0.0723(5) Uani 1 1 d . . . H10 H 0.9667(9) 0.634(2) 0.2774(8) 0.085(6) Uiso 1 1 d . . . C11 C 0.87589(8) 0.6041(2) 0.29470(8) 0.0533(4) Uani 1 1 d . . . C12 C 0.89417(9) 0.6531(2) 0.35840(9) 0.0576(5) Uani 1 1 d . . . H12 H 0.9394(8) 0.688(2) 0.3778(7) 0.070(5) Uiso 1 1 d . . . C13 C 0.84962(8) 0.6525(2) 0.39720(8) 0.0512(4) Uani 1 1 d . . . C14 C 0.86887(11) 0.7052(2) 0.46252(9) 0.0639(5) Uani 1 1 d . . . H14 H 0.9120(9) 0.740(2) 0.4755(7) 0.069(5) Uiso 1 1 d . . . C15 C 0.82562(12) 0.7044(3) 0.50009(10) 0.0731(6) Uani 1 1 d . . . H15 H 0.8406(8) 0.737(2) 0.5434(8) 0.079(6) Uiso 1 1 d . . . C16 C 0.75958(11) 0.6493(3) 0.47522(9) 0.0728(6) Uani 1 1 d . . . H16 H 0.7297(9) 0.653(3) 0.5027(9) 0.098(7) Uiso 1 1 d . . . C17 C 0.73815(10) 0.6010(2) 0.41351(9) 0.0618(5) Uani 1 1 d . . . H17 H 0.6907(9) 0.566(2) 0.3955(8) 0.076(5) Uiso 1 1 d . . . C18 C 0.78199(7) 0.5999(2) 0.37119(7) 0.0476(4) Uani 1 1 d . . . C19 C 0.40364(11) 0.3140(3) 0.46884(9) 0.0820(6) Uani 1 1 d . . . H19A H 0.3679 0.2337 0.4499 0.085(6) Uiso 1 1 calc R . . H19B H 0.3866 0.4352 0.4699 0.117(8) Uiso 1 1 calc R . . H19C H 0.4233 0.2746 0.5114 0.114(8) Uiso 1 1 calc R . . C20 C 0.45543(11) 0.3121(4) 0.43024(9) 0.0729(6) Uani 1 1 d . . . H20A H 0.4871(9) 0.402(2) 0.4450(8) 0.077(6) Uiso 1 1 d . . . H20B H 0.4746(9) 0.190(3) 0.4305(8) 0.089(7) Uiso 1 1 d . . . C21 C 0.45570(8) 0.4405(2) 0.32457(8) 0.0516(4) Uani 1 1 d . . . C22 C 0.31284(8) 0.4910(2) 0.20278(8) 0.0499(4) Uani 1 1 d . . . H22 H 0.3297(7) 0.5563(19) 0.1730(7) 0.054(5) Uiso 1 1 d . . . C23 C 0.24099(7) 0.45780(18) 0.18777(7) 0.0436(4) Uani 1 1 d . . . C24 C 0.20391(8) 0.46080(18) 0.23551(7) 0.0443(4) Uani 1 1 d . . . C25 C 0.23099(10) 0.5075(2) 0.30017(8) 0.0538(4) Uani 1 1 d . . . H25 H 0.2747(8) 0.5377(19) 0.3132(7) 0.050(5) Uiso 1 1 d . . . C26 C 0.19320(10) 0.5097(2) 0.34369(9) 0.0646(5) Uani 1 1 d . . . H26 H 0.2144(7) 0.5460(19) 0.3881(7) 0.060(5) Uiso 1 1 d . . . C27 C 0.12459(11) 0.4653(3) 0.32607(10) 0.0708(6) Uani 1 1 d . . . H27 H 0.0998(8) 0.469(2) 0.3576(8) 0.071(5) Uiso 1 1 d . . . C28 C 0.09646(10) 0.4230(2) 0.26551(10) 0.0637(5) Uani 1 1 d . . . H28 H 0.0509(9) 0.390(2) 0.2539(8) 0.077(6) Uiso 1 1 d . . . C29 C 0.13406(8) 0.41981(19) 0.21826(8) 0.0491(4) Uani 1 1 d . . . C30 C 0.10421(9) 0.3751(2) 0.15571(8) 0.0547(4) Uani 1 1 d . . . H30 H 0.0582(8) 0.3416(18) 0.1455(7) 0.056(4) Uiso 1 1 d . . . C31 C 0.13932(8) 0.3732(2) 0.10851(7) 0.0492(4) Uani 1 1 d . . . C32 C 0.10793(11) 0.3261(2) 0.04457(9) 0.0642(5) Uani 1 1 d . . . H32 H 0.0628(8) 0.297(2) 0.0384(7) 0.070(5) Uiso 1 1 d . . . C33 C 0.14209(11) 0.3213(3) -0.00125(9) 0.0719(6) Uani 1 1 d . . . H33 H 0.1210(8) 0.288(2) -0.0428(8) 0.079(6) Uiso 1 1 d . . . C34 C 0.21035(11) 0.3659(3) 0.01344(9) 0.0690(5) Uani 1 1 d . . . H34 H 0.2356(8) 0.358(2) -0.0192(8) 0.071(5) Uiso 1 1 d . . . C35 C 0.24240(10) 0.4107(2) 0.07363(8) 0.0586(5) Uani 1 1 d . . . H35 H 0.2892(8) 0.4366(19) 0.0824(7) 0.059(5) Uiso 1 1 d . . . C36 C 0.20875(7) 0.41828(19) 0.12404(7) 0.0449(4) Uani 1 1 d . . . N1 N 0.59151(8) 0.6678(2) 0.11061(7) 0.0623(4) Uani 1 1 d . . . H1D H 0.6334(9) 0.685(2) 0.1272(8) 0.077(6) Uiso 1 1 d . . . N2 N 0.59196(7) 0.5599(2) 0.20861(7) 0.0554(4) Uani 1 1 d . . . H2D H 0.5737(8) 0.526(2) 0.2350(7) 0.046(5) Uiso 1 1 d . . . N3 N 0.65950(6) 0.58716(16) 0.22519(6) 0.0520(3) Uani 1 1 d . . . N4 N 0.42544(8) 0.3580(2) 0.36450(7) 0.0668(5) Uani 1 1 d . . . H4D H 0.3864(8) 0.327(2) 0.3486(7) 0.058(5) Uiso 1 1 d . . . N5 N 0.41705(7) 0.4707(2) 0.26581(7) 0.0558(4) Uani 1 1 d . . . H5D H 0.4316(8) 0.524(2) 0.2385(8) 0.058(6) Uiso 1 1 d . . . N6 N 0.35048(6) 0.43122(16) 0.25435(6) 0.0523(3) Uani 1 1 d . . . S1 S 0.47373(2) 0.57202(8) 0.13050(2) 0.08052(19) Uani 1 1 d . . . S2 S 0.53494(2) 0.51246(7) 0.34370(2) 0.07138(17) 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 0.0916(18) 0.0822(17) 0.0708(15) -0.0055(13) 0.0221(14) -0.0127(15) C2 0.0622(14) 0.0752(15) 0.0609(13) 0.0005(10) -0.0075(11) -0.0057(12) C3 0.0411(10) 0.0580(10) 0.0525(10) -0.0111(8) -0.0017(9) 0.0050(8) C4 0.0377(9) 0.0568(10) 0.0504(10) -0.0005(8) 0.0007(8) -0.0046(8) C5 0.0377(9) 0.0443(9) 0.0487(9) 0.0018(7) 0.0019(7) -0.0012(7) C6 0.0444(10) 0.0415(9) 0.0514(10) 0.0048(7) 0.0041(8) 0.0002(7) C7 0.0560(12) 0.0561(11) 0.0570(11) 0.0013(8) 0.0092(10) 0.0015(9) C8 0.0803(16) 0.0748(13) 0.0604(13) 0.0023(10) 0.0221(12) 0.0058(11) C9 0.0679(16) 0.0932(15) 0.0865(17) 0.0095(12) 0.0371(14) 0.0045(12) C10 0.0513(13) 0.0812(14) 0.0858(16) 0.0085(12) 0.0188(12) -0.0010(11) C11 0.0418(10) 0.0519(10) 0.0652(12) 0.0095(8) 0.0104(9) -0.0009(8) C12 0.0383(10) 0.0590(11) 0.0669(13) 0.0073(9) -0.0049(9) -0.0077(8) C13 0.0422(10) 0.0489(9) 0.0549(10) 0.0028(8) -0.0042(8) -0.0016(8) C14 0.0560(13) 0.0620(12) 0.0610(13) -0.0018(9) -0.0119(11) -0.0057(10) C15 0.0852(17) 0.0769(14) 0.0495(12) -0.0045(10) 0.0001(12) 0.0070(12) C16 0.0705(15) 0.0924(15) 0.0545(13) -0.0037(10) 0.0121(12) 0.0101(11) C17 0.0493(12) 0.0758(13) 0.0574(12) 0.0003(9) 0.0064(10) 0.0043(10) C18 0.0404(9) 0.0479(9) 0.0495(10) 0.0049(7) 0.0004(8) 0.0018(7) C19 0.0937(16) 0.0816(16) 0.0692(14) -0.0090(11) 0.0160(13) -0.0150(13) C20 0.0630(14) 0.0921(17) 0.0537(12) 0.0053(11) -0.0068(10) -0.0087(13) C21 0.0404(10) 0.0590(10) 0.0501(10) -0.0084(8) -0.0003(8) 0.0050(8) C22 0.0403(10) 0.0574(10) 0.0477(10) 0.0031(8) 0.0014(8) -0.0071(8) C23 0.0379(9) 0.0407(9) 0.0466(9) 0.0050(7) -0.0017(7) -0.0028(7) C24 0.0413(9) 0.0405(9) 0.0467(9) 0.0039(7) 0.0011(8) -0.0017(7) C25 0.0514(12) 0.0549(11) 0.0509(11) -0.0038(8) 0.0035(9) -0.0038(9) C26 0.0743(15) 0.0643(12) 0.0532(12) -0.0065(9) 0.0109(11) -0.0026(10) C27 0.0758(16) 0.0774(13) 0.0664(14) -0.0011(10) 0.0311(13) 0.0026(11) C28 0.0495(12) 0.0710(13) 0.0720(14) 0.0041(10) 0.0171(11) -0.0011(10) C29 0.0422(10) 0.0468(9) 0.0563(10) 0.0060(8) 0.0069(8) -0.0008(7) C30 0.0351(10) 0.0614(11) 0.0607(11) 0.0065(8) -0.0028(9) -0.0073(8) C31 0.0439(10) 0.0474(9) 0.0486(10) 0.0052(7) -0.0051(8) -0.0039(7) C32 0.0538(13) 0.0731(13) 0.0559(12) 0.0031(9) -0.0072(10) -0.0109(10) C33 0.0755(15) 0.0822(14) 0.0474(12) -0.0042(10) -0.0077(11) -0.0050(11) C34 0.0699(14) 0.0869(14) 0.0475(11) 0.0036(10) 0.0083(11) 0.0038(11) C35 0.0502(12) 0.0704(12) 0.0514(11) 0.0077(9) 0.0038(9) -0.0013(9) C36 0.0401(9) 0.0460(9) 0.0442(9) 0.0072(7) 0.0010(7) -0.0010(7) N1 0.0426(10) 0.0792(11) 0.0569(10) 0.0043(8) -0.0052(8) -0.0056(8) N2 0.0346(9) 0.0775(11) 0.0495(9) -0.0016(8) 0.0003(7) -0.0029(7) N3 0.0360(8) 0.0565(8) 0.0566(9) -0.0021(7) -0.0033(7) -0.0024(6) N4 0.0467(10) 0.0858(11) 0.0564(10) 0.0086(8) -0.0115(8) -0.0161(8) N5 0.0369(9) 0.0755(10) 0.0503(9) 0.0045(8) 0.0004(7) -0.0062(7) N6 0.0358(8) 0.0596(8) 0.0548(8) 0.0009(7) -0.0034(6) -0.0063(6) S1 0.0362(3) 0.1371(5) 0.0618(3) -0.0071(3) -0.0019(2) 0.0043(3) S2 0.0341(3) 0.1146(4) 0.0608(3) -0.0120(3) 0.0015(2) -0.0025(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 C1 C2 1.499(3) . ? C1 H1A 1.01(2) . ? C1 H1B 1.06(2) . ? C1 H1C 0.984(19) . ? C2 N1 1.459(2) . ? C2 H2A 0.981(17) . ? C2 H2B 0.969(17) . ? C3 N1 1.323(2) . ? C3 N2 1.348(2) . ? C3 S1 1.6773(17) . ? C4 N3 1.2785(19) . ? C4 C5 1.462(2) . ? C4 H4 0.975(15) . ? C5 C18 1.416(2) . ? C5 C6 1.417(2) . ? C6 C7 1.422(2) . ? C6 C11 1.438(2) . ? C7 C8 1.360(3) . ? C7 H7 0.952(15) . ? C8 C9 1.407(3) . ? C8 H8 0.980(17) . ? C9 C10 1.338(3) . ? C9 H9 0.937(19) . ? C10 C11 1.422(2) . ? C10 H10 0.940(18) . ? C11 C12 1.389(2) . ? C12 C13 1.381(2) . ? C12 H12 0.966(16) . ? C13 C14 1.429(2) . ? C13 C18 1.431(2) . ? C14 C15 1.339(3) . ? C14 H14 0.903(16) . ? C15 C16 1.403(3) . ? C15 H15 0.947(16) . ? C16 C17 1.352(2) . ? C16 H16 0.951(18) . ? C17 C18 1.428(2) . ? C17 H17 0.999(17) . ? C19 C20 1.500(3) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 N4 1.452(2) . ? C20 H20A 0.930(18) . ? C20 H20B 0.984(18) . ? C21 N4 1.324(2) . ? C21 N5 1.3524(19) . ? C21 S2 1.6756(17) . ? C22 N6 1.2798(19) . ? C22 C23 1.462(2) . ? C22 H22 0.932(15) . ? C23 C36 1.415(2) . ? C23 C24 1.420(2) . ? C24 C25 1.422(2) . ? C24 C29 1.434(2) . ? C25 C26 1.354(2) . ? C25 H25 0.907(15) . ? C26 C27 1.415(3) . ? C26 H26 0.995(15) . ? C27 C28 1.340(3) . ? C27 H27 0.944(17) . ? C28 C29 1.419(2) . ? C28 H28 0.945(17) . ? C29 C30 1.390(2) . ? C30 C31 1.382(2) . ? C30 H30 0.955(15) . ? C31 C32 1.427(2) . ? C31 C36 1.432(2) . ? C32 C33 1.343(3) . ? C32 H32 0.933(16) . ? C33 C34 1.408(3) . ? C33 H33 0.935(16) . ? C34 C35 1.357(2) . ? C34 H34 0.971(15) . ? C35 C36 1.423(2) . ? C35 H35 0.959(15) . ? N1 H1D 0.865(17) . ? N2 N3 1.3700(17) . ? N2 H2D 0.794(14) . ? N4 H4D 0.829(15) . ? N5 N6 1.3684(17) . ? N5 H5D 0.822(15) . ? 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 H1A 108.8(10) . . ? C2 C1 H1B 112.6(11) . . ? H1A C1 H1B 107.1(16) . . ? C2 C1 H1C 109.7(12) . . ? H1A C1 H1C 110.2(16) . . ? H1B C1 H1C 108.4(16) . . ? N1 C2 C1 110.42(18) . . ? N1 C2 H2A 105.9(10) . . ? C1 C2 H2A 113.8(10) . . ? N1 C2 H2B 108.7(9) . . ? C1 C2 H2B 109.7(9) . . ? H2A C2 H2B 108.2(14) . . ? N1 C3 N2 115.64(15) . . ? N1 C3 S1 124.29(14) . . ? N2 C3 S1 120.02(14) . . ? N3 C4 C5 122.14(16) . . ? N3 C4 H4 121.6(9) . . ? C5 C4 H4 116.3(9) . . ? C18 C5 C6 120.30(14) . . ? C18 C5 C4 117.75(14) . . ? C6 C5 C4 121.90(14) . . ? C5 C6 C7 124.13(15) . . ? C5 C6 C11 118.74(14) . . ? C7 C6 C11 117.11(16) . . ? C8 C7 C6 121.29(19) . . ? C8 C7 H7 120.0(9) . . ? C6 C7 H7 118.6(9) . . ? C7 C8 C9 120.9(2) . . ? C7 C8 H8 118.7(10) . . ? C9 C8 H8 120.3(10) . . ? C10 C9 C8 120.1(2) . . ? C10 C9 H9 120.4(12) . . ? C8 C9 H9 119.5(12) . . ? C9 C10 C11 121.5(2) . . ? C9 C10 H10 123.9(11) . . ? C11 C10 H10 114.6(11) . . ? C12 C11 C10 121.34(17) . . ? C12 C11 C6 119.57(16) . . ? C10 C11 C6 119.09(17) . . ? C13 C12 C11 122.43(16) . . ? C13 C12 H12 116.7(9) . . ? C11 C12 H12 120.9(9) . . ? C12 C13 C14 121.90(16) . . ? C12 C13 C18 119.17(15) . . ? C14 C13 C18 118.92(17) . . ? C15 C14 C13 121.83(19) . . ? C15 C14 H14 124.0(11) . . ? C13 C14 H14 114.2(11) . . ? C14 C15 C16 119.52(19) . . ? C14 C15 H15 119.3(10) . . ? C16 C15 H15 121.1(10) . . ? C17 C16 C15 121.3(2) . . ? C17 C16 H16 120.9(12) . . ? C15 C16 H16 117.7(12) . . ? C16 C17 C18 121.55(19) . . ? C16 C17 H17 121.2(10) . . ? C18 C17 H17 117.3(10) . . ? C5 C18 C17 123.48(15) . . ? C5 C18 C13 119.64(14) . . ? C17 C18 C13 116.81(15) . . ? C20 C19 H19A 109.5 . . ? C20 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C20 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N4 C20 C19 110.25(17) . . ? N4 C20 H20A 106.0(11) . . ? C19 C20 H20A 109.6(11) . . ? N4 C20 H20B 107.3(10) . . ? C19 C20 H20B 110.1(11) . . ? H20A C20 H20B 113.4(15) . . ? N4 C21 N5 115.08(15) . . ? N4 C21 S2 124.33(13) . . ? N5 C21 S2 120.55(14) . . ? N6 C22 C23 120.96(16) . . ? N6 C22 H22 122.1(9) . . ? C23 C22 H22 117.0(9) . . ? C36 C23 C24 120.05(14) . . ? C36 C23 C22 118.28(14) . . ? C24 C23 C22 121.66(14) . . ? C23 C24 C25 124.31(14) . . ? C23 C24 C29 119.05(14) . . ? C25 C24 C29 116.62(15) . . ? C26 C25 C24 121.89(18) . . ? C26 C25 H25 118.2(9) . . ? C24 C25 H25 119.9(9) . . ? C25 C26 C27 120.71(19) . . ? C25 C26 H26 118.7(9) . . ? C27 C26 H26 120.6(9) . . ? C28 C27 C26 119.72(19) . . ? C28 C27 H27 121.9(10) . . ? C26 C27 H27 118.4(10) . . ? C27 C28 C29 121.50(19) . . ? C27 C28 H28 119.8(10) . . ? C29 C28 H28 118.7(10) . . ? C30 C29 C28 120.81(16) . . ? C30 C29 C24 119.64(15) . . ? C28 C29 C24 119.55(16) . . ? C31 C30 C29 122.12(16) . . ? C31 C30 H30 119.2(9) . . ? C29 C30 H30 118.6(9) . . ? C30 C31 C32 121.38(16) . . ? C30 C31 C36 119.44(14) . . ? C32 C31 C36 119.18(16) . . ? C33 C32 C31 121.60(19) . . ? C33 C32 H32 124.3(10) . . ? C31 C32 H32 114.1(10) . . ? C32 C33 C34 119.70(19) . . ? C32 C33 H33 120.5(11) . . ? C34 C33 H33 119.8(11) . . ? C35 C34 C33 120.8(2) . . ? C35 C34 H34 119.3(10) . . ? C33 C34 H34 119.8(10) . . ? C34 C35 C36 121.95(18) . . ? C34 C35 H35 118.9(9) . . ? C36 C35 H35 119.2(9) . . ? C23 C36 C35 123.51(14) . . ? C23 C36 C31 119.64(14) . . ? C35 C36 C31 116.76(15) . . ? C3 N1 C2 125.47(16) . . ? C3 N1 H1D 115.3(11) . . ? C2 N1 H1D 119.0(11) . . ? C3 N2 N3 120.48(15) . . ? C3 N2 H2D 120.5(12) . . ? N3 N2 H2D 118.8(12) . . ? C4 N3 N2 116.26(14) . . ? C21 N4 C20 125.93(17) . . ? C21 N4 H4D 114.4(11) . . ? C20 N4 H4D 119.6(11) . . ? C21 N5 N6 118.88(15) . . ? C21 N5 H5D 121.3(12) . . ? N6 N5 H5D 119.3(12) . . ? C22 N6 N5 117.71(14) . . ? 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 N2 H2D S2 0.794(14) 2.655(15) 3.4109(19) 159.8(14) . N5 H5D S1 0.822(15) 2.697(16) 3.4745(18) 158.6(14) . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.214 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.032 data_2 _database_code_depnum_ccdc_archive 'CCDC 721345' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C37 H38 N6 O S2' _chemical_formula_weight 646.85 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' S S 0.1246 0.1234 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 18.946(4) _cell_length_b 8.8906(18) _cell_length_c 20.698(4) _cell_angle_alpha 90.00 _cell_angle_beta 104.51(3) _cell_angle_gamma 90.00 _cell_volume 3375.1(12) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3254 _cell_measurement_theta_min 2.221 _cell_measurement_theta_max 24.891 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.273 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1368 _exptl_absorpt_coefficient_mu 0.197 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.821193 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Bruker SMART APEX-CCD' _diffrn_measurement_method '\omega scans' _diffrn_detector_area_resol_mean 15X15microns _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9169 _diffrn_reflns_av_R_equivalents 0.0276 _diffrn_reflns_av_sigmaI/netI 0.0278 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 25.06 _reflns_number_total 2985 _reflns_number_gt 2535 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART :BRUKER MOLECULAR ANALYSIS Research ToolV5.618 Copyr.1997-00 BrukerAXS' _computing_cell_refinement 'SMART :BRUKER MOLECULAR ANALYSIS Research ToolV5.618 Copyr.1997-00 BrukerAXS' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL V5.1 (Sheldrick, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^ > 2sigma(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. The four hydrogen atoms belonging to this methanol molecule have not been included in the refinement due to the disorder of the solvent molecule.The bond lengths of C(19)-O(2) and C(19)-O(1) is rather short, which may be caused by the H-bonding interations of this group, therefore,restraint DFIX was used in order to control the geometry. The H-bonds may be affected by the disorder of the methanol molecule. ; _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^)+(0.0638P)^2^+2.0864P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2985 _refine_ls_number_parameters 285 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0625 _refine_ls_R_factor_gt 0.0531 _refine_ls_wR_factor_ref 0.1371 _refine_ls_wR_factor_gt 0.1319 _refine_ls_goodness_of_fit_ref 1.146 _refine_ls_restrained_S_all 1.158 _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 C1 C 0.3294(2) 0.4408(5) 0.36240(19) 0.0827(11) Uani 1 1 d . . . H1A H 0.297(3) 0.422(5) 0.396(2) 0.137(17) Uiso 1 1 d . . . H1B H 0.3215(18) 0.550(4) 0.3468(16) 0.085(10) Uiso 1 1 d . . . H1C H 0.378(2) 0.430(4) 0.3838(19) 0.097(12) Uiso 1 1 d . . . C2 C 0.31400(15) 0.3356(4) 0.30427(15) 0.0590(7) Uani 1 1 d . . . H2A H 0.3189(15) 0.233(3) 0.3207(14) 0.069(8) Uiso 1 1 d . . . H2B H 0.3450(18) 0.349(4) 0.2775(17) 0.085(11) Uiso 1 1 d . . . C3 C 0.18433(13) 0.2692(3) 0.26743(11) 0.0414(5) Uani 1 1 d . . . C4 C 0.04317(14) 0.4502(3) 0.15220(12) 0.0450(6) Uani 1 1 d . . . H4 H 0.0061(15) 0.387(3) 0.1576(13) 0.056(7) Uiso 1 1 d . . . C5 C 0.01967(13) 0.5739(3) 0.10495(11) 0.0430(5) Uani 1 1 d . . . C6 C 0.06007(14) 0.6184(3) 0.05900(11) 0.0464(6) Uani 1 1 d . . . C7 C 0.12715(15) 0.5539(3) 0.05551(13) 0.0542(7) Uani 1 1 d . . . H7 H 0.1460(14) 0.477(3) 0.0838(13) 0.052(7) Uiso 1 1 d . . . C8 C 0.16370(19) 0.6009(4) 0.01088(15) 0.0674(8) Uani 1 1 d . . . H8 H 0.207(2) 0.555(4) 0.0062(18) 0.095(12) Uiso 1 1 d . . . C9 C 0.1357(2) 0.7163(4) -0.03444(16) 0.0741(10) Uani 1 1 d . . . H9 H 0.1624(18) 0.745(4) -0.0621(17) 0.083(10) Uiso 1 1 d . . . C10 C 0.0722(2) 0.7794(4) -0.03451(14) 0.0672(9) Uani 1 1 d . . . H10 H 0.0540(16) 0.851(3) -0.0614(15) 0.064(9) Uiso 1 1 d . . . C11 C 0.03062(15) 0.7344(3) 0.01135(12) 0.0527(7) Uani 1 1 d . . . C12 C -0.03630(18) 0.7972(3) 0.01086(14) 0.0618(8) Uani 1 1 d . . . H12 H -0.0541(18) 0.868(4) -0.0174(16) 0.075(9) Uiso 1 1 d . . . C13 C -0.07695(15) 0.7542(3) 0.05517(14) 0.0567(7) Uani 1 1 d . . . C14 C -0.14602(19) 0.8187(4) 0.05308(19) 0.0744(9) Uani 1 1 d . . . H14 H -0.1649(19) 0.894(4) 0.0185(18) 0.091(11) Uiso 1 1 d . . . C15 C -0.1849(2) 0.7757(4) 0.0964(2) 0.0831(11) Uani 1 1 d . . . H15 H -0.233(2) 0.812(4) 0.0944(17) 0.101(12) Uiso 1 1 d . . . C16 C -0.15588(18) 0.6681(4) 0.14627(19) 0.0733(9) Uani 1 1 d . . . H16 H -0.1837(18) 0.639(4) 0.1766(16) 0.080(10) Uiso 1 1 d . . . C17 C -0.09020(16) 0.6042(3) 0.14983(15) 0.0593(7) Uani 1 1 d . . . H17 H -0.0717(15) 0.538(3) 0.1836(14) 0.062(8) Uiso 1 1 d . . . C18 C -0.04802(14) 0.6416(3) 0.10398(12) 0.0491(6) Uani 1 1 d . . . N1 N 0.24033(11) 0.3522(2) 0.26215(10) 0.0513(5) Uani 1 1 d D . . H1D H 0.2315(14) 0.425(2) 0.2347(11) 0.055(8) Uiso 1 1 d D . . N2 N 0.11819(11) 0.3044(2) 0.22725(10) 0.0484(5) Uani 1 1 d . . . H2D H 0.0813(16) 0.248(3) 0.2280(13) 0.058 Uiso 1 1 d . . . N3 N 0.10892(11) 0.4276(2) 0.18562(10) 0.0454(5) Uani 1 1 d . . . S1 S 0.18918(4) 0.12160(7) 0.31981(3) 0.0503(2) Uani 1 1 d . . . O1 O 0.0111(8) 0.0952(10) 0.2820(7) 0.060(3) Uani 0.25 1 d PD . . O2 O 0.0000 0.1088(8) 0.2500 0.113(8) Uani 0.50 2 d SPD . . C19 C 0.0000 -0.0450(6) 0.2500 0.132(3) Uani 1 2 d SD . . 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 0.081(3) 0.076(2) 0.071(2) 0.0019(19) -0.018(2) 0.0024(19) C2 0.0440(15) 0.0623(18) 0.0638(18) 0.0138(15) 0.0005(13) 0.0014(13) C3 0.0473(14) 0.0413(13) 0.0347(11) -0.0010(10) 0.0086(10) 0.0047(10) C4 0.0422(14) 0.0449(13) 0.0441(13) 0.0025(11) 0.0040(11) -0.0050(11) C5 0.0462(13) 0.0388(12) 0.0377(12) 0.0017(10) -0.0010(10) -0.0055(10) C6 0.0538(15) 0.0416(13) 0.0375(12) -0.0019(10) -0.0007(10) -0.0098(11) C7 0.0562(16) 0.0588(16) 0.0446(14) 0.0006(13) 0.0070(12) -0.0059(13) C8 0.073(2) 0.079(2) 0.0526(16) -0.0055(15) 0.0201(15) -0.0157(17) C9 0.094(3) 0.080(2) 0.0519(18) -0.0034(16) 0.0257(17) -0.030(2) C10 0.099(3) 0.0535(17) 0.0425(15) 0.0077(14) 0.0058(16) -0.0203(17) C11 0.0687(18) 0.0405(13) 0.0404(13) 0.0007(11) -0.0024(12) -0.0117(12) C12 0.080(2) 0.0397(14) 0.0527(16) 0.0096(13) -0.0079(14) -0.0023(14) C13 0.0606(17) 0.0406(14) 0.0578(16) -0.0015(12) -0.0060(13) 0.0006(12) C14 0.069(2) 0.0530(18) 0.090(2) 0.0003(17) -0.0027(18) 0.0128(15) C15 0.060(2) 0.066(2) 0.114(3) -0.020(2) 0.005(2) 0.0162(17) C16 0.0607(19) 0.073(2) 0.087(2) -0.0150(18) 0.0191(17) 0.0009(16) C17 0.0551(17) 0.0584(17) 0.0619(17) -0.0008(15) 0.0100(13) 0.0012(13) C18 0.0504(15) 0.0409(13) 0.0489(14) -0.0032(11) -0.0007(11) -0.0039(11) N1 0.0478(12) 0.0510(13) 0.0501(13) 0.0152(10) 0.0031(10) 0.0014(10) N2 0.0434(12) 0.0474(12) 0.0501(12) 0.0116(10) 0.0036(9) -0.0025(9) N3 0.0475(12) 0.0436(11) 0.0410(10) 0.0057(9) 0.0036(9) -0.0007(9) S1 0.0587(4) 0.0471(4) 0.0444(4) 0.0102(3) 0.0116(3) 0.0088(3) O1 0.040(5) 0.083(8) 0.059(7) 0.024(5) 0.014(4) 0.013(4) O2 0.158(17) 0.051(5) 0.179(19) 0.000 0.133(16) 0.000 C19 0.070(4) 0.069(4) 0.255(9) 0.000 0.039(5) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 C1 C2 1.494(5) . ? C1 H1A 1.05(5) . ? C1 H1B 1.02(3) . ? C1 H1C 0.92(4) . ? C2 N1 1.456(3) . ? C2 H2A 0.97(3) . ? C2 H2B 0.91(3) . ? C3 N1 1.319(3) . ? C3 N2 1.355(3) . ? C3 S1 1.690(2) . ? C4 N3 1.280(3) . ? C4 C5 1.465(3) . ? C4 H4 0.93(3) . ? C5 C18 1.412(3) . ? C5 C6 1.419(3) . ? C6 C7 1.413(4) . ? C6 C11 1.439(3) . ? C7 C8 1.352(4) . ? C7 H7 0.91(3) . ? C8 C9 1.402(5) . ? C8 H8 0.94(4) . ? C9 C10 1.328(5) . ? C9 H9 0.89(3) . ? C10 C11 1.433(4) . ? C10 H10 0.86(3) . ? C11 C12 1.383(4) . ? C12 C13 1.391(4) . ? C12 H12 0.87(3) . ? C13 C14 1.419(4) . ? C13 C18 1.430(3) . ? C14 C15 1.352(5) . ? C14 H14 0.98(4) . ? C15 C16 1.413(5) . ? C15 H15 0.97(4) . ? C16 C17 1.353(4) . ? C16 H16 0.95(3) . ? C17 C18 1.425(4) . ? C17 H17 0.91(3) . ? N1 H1D 0.851(10) . ? N2 N3 1.377(3) . ? N2 H2D 0.86(3) . ? O1 O2 0.655(13) . ? O1 O1 1.29(3) 2 ? O1 C19 1.403(9) . ? O2 O1 0.655(13) 2 ? O2 C19 1.368(8) . ? C19 O1 1.403(9) 2 ? 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 H1A 114(3) . . ? C2 C1 H1B 110.9(19) . . ? H1A C1 H1B 107(3) . . ? C2 C1 H1C 107(2) . . ? H1A C1 H1C 110(3) . . ? H1B C1 H1C 108(3) . . ? N1 C2 C1 112.6(3) . . ? N1 C2 H2A 107.4(17) . . ? C1 C2 H2A 108.8(17) . . ? N1 C2 H2B 107(2) . . ? C1 C2 H2B 113(2) . . ? H2A C2 H2B 108(3) . . ? N1 C3 N2 117.3(2) . . ? N1 C3 S1 124.87(18) . . ? N2 C3 S1 117.79(18) . . ? N3 C4 C5 124.8(2) . . ? N3 C4 H4 120.2(16) . . ? C5 C4 H4 115.0(16) . . ? C18 C5 C6 120.8(2) . . ? C18 C5 C4 116.9(2) . . ? C6 C5 C4 122.2(2) . . ? C7 C6 C5 124.4(2) . . ? C7 C6 C11 117.1(2) . . ? C5 C6 C11 118.5(2) . . ? C8 C7 C6 122.1(3) . . ? C8 C7 H7 119.0(16) . . ? C6 C7 H7 118.9(16) . . ? C7 C8 C9 120.7(3) . . ? C7 C8 H8 123(2) . . ? C9 C8 H8 116(2) . . ? C10 C9 C8 120.1(3) . . ? C10 C9 H9 123(2) . . ? C8 C9 H9 117(2) . . ? C9 C10 C11 122.0(3) . . ? C9 C10 H10 122(2) . . ? C11 C10 H10 116(2) . . ? C12 C11 C10 122.5(3) . . ? C12 C11 C6 119.4(2) . . ? C10 C11 C6 118.1(3) . . ? C11 C12 C13 122.8(3) . . ? C11 C12 H12 120(2) . . ? C13 C12 H12 117(2) . . ? C12 C13 C14 121.8(3) . . ? C12 C13 C18 118.7(3) . . ? C14 C13 C18 119.4(3) . . ? C15 C14 C13 121.2(3) . . ? C15 C14 H14 121(2) . . ? C13 C14 H14 118(2) . . ? C14 C15 C16 119.9(3) . . ? C14 C15 H15 123(2) . . ? C16 C15 H15 117(2) . . ? C17 C16 C15 120.6(3) . . ? C17 C16 H16 120(2) . . ? C15 C16 H16 119(2) . . ? C16 C17 C18 121.8(3) . . ? C16 C17 H17 118.9(18) . . ? C18 C17 H17 119.2(18) . . ? C5 C18 C17 123.4(2) . . ? C5 C18 C13 119.6(2) . . ? C17 C18 C13 117.0(2) . . ? C3 N1 C2 124.4(2) . . ? C3 N1 H1D 117.1(18) . . ? C2 N1 H1D 118.3(18) . . ? C3 N2 N3 121.4(2) . . ? C3 N2 H2D 118.8(18) . . ? N3 N2 H2D 119.8(18) . . ? C4 N3 N2 114.7(2) . . ? O2 O1 O1 10.7(12) . 2 ? O2 O1 C19 73.4(12) . . ? O1 O1 C19 62.7(5) 2 . ? O1 O2 O1 159(2) 2 . ? O1 O2 C19 79.3(12) 2 . ? O1 O2 C19 79.3(12) . . ? O2 C19 O1 27.3(5) . . ? O2 C19 O1 27.3(5) . 2 ? O1 C19 O1 54.6(11) . 2 ? 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 N2 H2D O2 0.86(3) 2.11(3) 2.965(5) 169(2) . N2 H2D O1 0.86(3) 2.37(3) 3.164(13) 153(2) . N2 H2D O1 0.86(3) 2.18(3) 3.044(13) 173(2) 2 N1 H1D S1 0.851(10) 2.726(19) 3.396(2) 137(2) 4 C9 H9 S1 0.89(3) 2.88(3) 3.706(3) 156(3) 6_565 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.06 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.376 _refine_diff_density_min -0.200 _refine_diff_density_rms 0.046