# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2008 data_global _journal_name_full 'New J.Chem.' _journal_coden_Cambridge 0440 _publ_contact_author_name 'Thomas C. W. Mak' _publ_contact_author_email TCWMAK@CUHK.EDU.HK _publ_section_title ; Intermolecular S***? Interaction in Crystalline Sulfanyl-triazine Derivates ; loop_ _publ_author_name 'Thomas C. W. Mak' 'Jie Han' 'Chong-Qing Wan' # Attachment 'CIF_cpd_1_and_3.txt' data_compound1 _database_code_depnum_ccdc_archive 'CCDC 704194' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H9 N9 S3' _chemical_formula_weight 411.49 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 11.814(3) _cell_length_b 11.411(3) _cell_length_c 13.428(3) _cell_angle_alpha 90.00 _cell_angle_beta 99.290(6) _cell_angle_gamma 90.00 _cell_volume 1786.3(8) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.41 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.530 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 0.437 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.734255 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 8883 _diffrn_reflns_av_R_equivalents 0.0583 _diffrn_reflns_av_sigmaI/netI 0.0813 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 25.01 _reflns_number_total 3146 _reflns_number_gt 1609 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0621P)^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 contr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3146 _refine_ls_number_parameters 224 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1294 _refine_ls_R_factor_gt 0.0567 _refine_ls_wR_factor_ref 0.1443 _refine_ls_wR_factor_gt 0.1159 _refine_ls_goodness_of_fit_ref 0.980 _refine_ls_restrained_S_all 0.980 _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 S1 S 0.71373(11) 0.33756(12) 0.28741(9) 0.0683(4) Uani 1 1 d . . . S2 S 0.72194(11) 0.48489(12) 0.66699(9) 0.0679(4) Uani 1 1 d . . . S3 S 0.97334(10) 0.68246(12) 0.42710(10) 0.0703(4) Uani 1 1 d . . . N1 N 0.7183(3) 0.4149(3) 0.4755(3) 0.0501(9) Uani 1 1 d . . . N2 N 0.8383(3) 0.5742(3) 0.5400(3) 0.0569(10) Uani 1 1 d . . . N3 N 0.8390(3) 0.5063(3) 0.3730(3) 0.0593(10) Uani 1 1 d . . . C5 C 0.5057(4) 0.3973(4) 0.6127(3) 0.0679(14) Uiso 1 1 d . . . H5A H 0.4869 0.4725 0.5888 0.082 Uiso 1 1 calc R . . C7 C 0.5650(5) 0.1920(5) 0.6877(4) 0.0932(18) Uiso 1 1 d . . . H7A H 0.5826 0.1185 0.7158 0.112 Uiso 1 1 calc R . . N4 N 0.4234(3) 0.3165(4) 0.6070(3) 0.0726(12) Uiso 1 1 d . . . C6 C 0.4543(4) 0.2140(5) 0.6441(4) 0.0764(15) Uiso 1 1 d . . . H6A H 0.4000 0.1545 0.6410 0.092 Uiso 1 1 calc R . . N5 N 0.6494(3) 0.2709(4) 0.6919(3) 0.0836(13) Uani 1 1 d . . . N8 N 0.8371(5) 0.9340(4) 0.5786(4) 0.0920(14) Uani 1 1 d . . . N9 N 1.0506(3) 0.8349(4) 0.5660(3) 0.0798(13) Uani 1 1 d . . . C1 C 0.7612(3) 0.4277(4) 0.3904(3) 0.0519(11) Uani 1 1 d . . . C2 C 0.7621(3) 0.4902(4) 0.5475(3) 0.0514(11) Uani 1 1 d . . . C3 C 0.8721(3) 0.5781(4) 0.4504(4) 0.0548(12) Uani 1 1 d . . . C4 C 0.6172(3) 0.3726(4) 0.6526(3) 0.0510(11) Uani 1 1 d . . . C8 C 0.6090(4) 0.2525(4) 0.3353(3) 0.0552(12) Uani 1 1 d . . . N6 N 0.5020(4) 0.2885(3) 0.3151(3) 0.0676(11) Uani 1 1 d . . . N7 N 0.5622(4) 0.0822(4) 0.4183(4) 0.1003(16) Uani 1 1 d . . . C9 C 0.4255(4) 0.2199(5) 0.3468(4) 0.0750(15) Uani 1 1 d . . . H9A H 0.3487 0.2417 0.3343 0.090 Uiso 1 1 calc R . . C10 C 0.4549(5) 0.1188(5) 0.3968(4) 0.0808(16) Uani 1 1 d . . . H10A H 0.3973 0.0732 0.4169 0.097 Uiso 1 1 calc R . . C11 C 0.6377(4) 0.1509(5) 0.3853(4) 0.0855(17) Uani 1 1 d . . . H11A H 0.7145 0.1287 0.3970 0.103 Uiso 1 1 calc R . . C12 C 0.9553(4) 0.7928(4) 0.5144(3) 0.0611(13) Uani 1 1 d . . . C13 C 0.8501(4) 0.8414(5) 0.5209(4) 0.0704(14) Uani 1 1 d . . . H13A H 0.7850 0.8081 0.4832 0.084 Uiso 1 1 calc R . . C14 C 0.9349(7) 0.9770(5) 0.6295(4) 0.094(2) Uani 1 1 d . . . H14A H 0.9323 1.0431 0.6696 0.113 Uiso 1 1 calc R . . C15 C 1.0376(6) 0.9271(6) 0.6241(5) 0.094(2) Uani 1 1 d . . . H15A H 1.1027 0.9587 0.6631 0.113 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 S1 0.0720(9) 0.0786(10) 0.0550(8) -0.0041(7) 0.0126(6) -0.0124(7) S2 0.0727(9) 0.0761(10) 0.0573(8) -0.0078(7) 0.0175(6) -0.0243(7) S3 0.0612(8) 0.0728(9) 0.0800(10) 0.0097(7) 0.0205(7) -0.0144(7) N1 0.045(2) 0.056(2) 0.049(2) 0.0020(19) 0.0026(18) -0.0029(18) N2 0.048(2) 0.063(3) 0.058(3) 0.0060(19) 0.0043(19) -0.008(2) N3 0.053(2) 0.066(3) 0.058(3) 0.006(2) 0.0103(19) -0.006(2) N5 0.057(3) 0.069(3) 0.116(4) 0.011(3) -0.013(2) -0.008(2) N8 0.104(4) 0.078(4) 0.099(4) -0.002(3) 0.032(3) -0.018(3) N9 0.067(3) 0.101(4) 0.067(3) 0.005(3) -0.004(2) -0.027(3) C1 0.043(3) 0.056(3) 0.056(3) 0.002(2) 0.003(2) 0.003(2) C2 0.035(2) 0.057(3) 0.060(3) 0.010(2) 0.004(2) 0.002(2) C3 0.041(3) 0.054(3) 0.067(4) 0.012(3) 0.004(2) -0.003(2) C4 0.048(3) 0.058(3) 0.047(3) -0.001(2) 0.007(2) 0.000(2) C8 0.054(3) 0.058(3) 0.051(3) -0.002(2) -0.002(2) -0.003(2) N6 0.062(3) 0.071(3) 0.068(3) 0.005(2) 0.005(2) 0.001(2) N7 0.076(3) 0.075(3) 0.150(5) 0.038(3) 0.018(3) 0.001(3) C9 0.056(3) 0.074(4) 0.093(4) 0.008(3) 0.003(3) -0.002(3) C10 0.071(4) 0.067(4) 0.102(5) -0.006(3) 0.010(3) -0.014(3) C11 0.062(4) 0.079(4) 0.114(5) 0.026(4) 0.011(3) 0.006(3) C12 0.053(3) 0.066(3) 0.062(3) 0.018(2) 0.003(2) -0.015(3) C13 0.057(3) 0.067(4) 0.084(4) 0.005(3) 0.002(3) -0.013(3) C14 0.129(6) 0.087(5) 0.075(4) -0.011(3) 0.044(4) -0.040(5) C15 0.100(5) 0.114(6) 0.068(4) -0.002(4) 0.011(4) -0.057(4) _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 S1 C1 1.742(4) . ? S1 C8 1.773(5) . ? S2 C2 1.746(5) . ? S2 C4 1.770(4) . ? S3 C3 1.752(4) . ? S3 C12 1.756(5) . ? N1 C1 1.332(5) . ? N1 C2 1.333(5) . ? N2 C3 1.328(5) . ? N2 C2 1.331(5) . ? N3 C3 1.331(5) . ? N3 C1 1.332(5) . ? C5 N4 1.333(5) . ? C5 C4 1.369(6) . ? C5 H5A 0.9300 . ? C7 N5 1.337(6) . ? C7 C6 1.367(6) . ? C7 H7A 0.9300 . ? N4 C6 1.300(6) . ? C6 H6A 0.9300 . ? N5 C4 1.306(5) . ? N8 C13 1.334(6) . ? N8 C14 1.338(7) . ? N9 C12 1.314(5) . ? N9 C15 1.333(7) . ? C8 N6 1.315(5) . ? C8 C11 1.355(6) . ? N6 C9 1.317(6) . ? N7 C11 1.317(6) . ? N7 C10 1.321(6) . ? C9 C10 1.352(6) . ? C9 H9A 0.9300 . ? C10 H10A 0.9300 . ? C11 H11A 0.9300 . ? C12 C13 1.376(6) . ? C13 H13A 0.9300 . ? C14 C15 1.353(8) . ? C14 H14A 0.9300 . ? C15 H15A 0.9300 . ? 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 C1 S1 C8 100.9(2) . . ? C2 S2 C4 102.3(2) . . ? C3 S3 C12 102.0(2) . . ? C1 N1 C2 113.2(4) . . ? C3 N2 C2 113.5(4) . . ? C3 N3 C1 113.6(4) . . ? N4 C5 C4 121.8(5) . . ? N4 C5 H5A 119.1 . . ? C4 C5 H5A 119.1 . . ? N5 C7 C6 123.4(6) . . ? N5 C7 H7A 118.3 . . ? C6 C7 H7A 118.3 . . ? C6 N4 C5 116.4(4) . . ? N4 C6 C7 121.2(5) . . ? N4 C6 H6A 119.4 . . ? C7 C6 H6A 119.4 . . ? C4 N5 C7 114.5(4) . . ? C13 N8 C14 114.6(5) . . ? C12 N9 C15 115.3(5) . . ? N1 C1 N3 126.4(4) . . ? N1 C1 S1 119.9(3) . . ? N3 C1 S1 113.7(4) . . ? N2 C2 N1 126.7(4) . . ? N2 C2 S2 112.4(4) . . ? N1 C2 S2 120.8(3) . . ? N2 C3 N3 126.4(4) . . ? N2 C3 S3 119.9(4) . . ? N3 C3 S3 113.7(4) . . ? N5 C4 C5 122.7(4) . . ? N5 C4 S2 116.5(3) . . ? C5 C4 S2 120.4(4) . . ? N6 C8 C11 121.7(5) . . ? N6 C8 S1 117.2(4) . . ? C11 C8 S1 121.0(4) . . ? C8 N6 C9 115.8(4) . . ? C11 N7 C10 114.7(5) . . ? N6 C9 C10 122.2(5) . . ? N6 C9 H9A 118.9 . . ? C10 C9 H9A 118.9 . . ? N7 C10 C9 122.5(5) . . ? N7 C10 H10A 118.7 . . ? C9 C10 H10A 118.7 . . ? N7 C11 C8 123.1(5) . . ? N7 C11 H11A 118.4 . . ? C8 C11 H11A 118.4 . . ? N9 C12 C13 121.7(5) . . ? N9 C12 S3 115.3(4) . . ? C13 C12 S3 122.6(4) . . ? N8 C13 C12 123.1(5) . . ? N8 C13 H13A 118.5 . . ? C12 C13 H13A 118.5 . . ? N8 C14 C15 121.8(6) . . ? N8 C14 H14A 119.1 . . ? C15 C14 H14A 119.1 . . ? N9 C15 C14 123.5(6) . . ? N9 C15 H15A 118.2 . . ? C14 C15 H15A 118.2 . . ? 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 C4 C5 N4 C6 1.9(7) . . . . ? C5 N4 C6 C7 0.9(7) . . . . ? N5 C7 C6 N4 -2.7(9) . . . . ? C6 C7 N5 C4 1.4(8) . . . . ? C2 N1 C1 N3 -0.7(6) . . . . ? C2 N1 C1 S1 -179.6(3) . . . . ? C3 N3 C1 N1 -1.4(6) . . . . ? C3 N3 C1 S1 177.5(3) . . . . ? C8 S1 C1 N1 1.9(4) . . . . ? C8 S1 C1 N3 -177.1(3) . . . . ? C3 N2 C2 N1 -0.9(6) . . . . ? C3 N2 C2 S2 178.5(3) . . . . ? C1 N1 C2 N2 2.0(6) . . . . ? C1 N1 C2 S2 -177.4(3) . . . . ? C4 S2 C2 N2 177.2(3) . . . . ? C4 S2 C2 N1 -3.3(4) . . . . ? C2 N2 C3 N3 -1.7(6) . . . . ? C2 N2 C3 S3 -179.4(3) . . . . ? C1 N3 C3 N2 2.7(6) . . . . ? C1 N3 C3 S3 -179.4(3) . . . . ? C12 S3 C3 N2 -24.6(4) . . . . ? C12 S3 C3 N3 157.3(3) . . . . ? C7 N5 C4 C5 1.5(7) . . . . ? C7 N5 C4 S2 174.0(4) . . . . ? N4 C5 C4 N5 -3.3(7) . . . . ? N4 C5 C4 S2 -175.5(3) . . . . ? C2 S2 C4 N5 103.3(4) . . . . ? C2 S2 C4 C5 -84.0(4) . . . . ? C1 S1 C8 N6 94.5(4) . . . . ? C1 S1 C8 C11 -89.4(4) . . . . ? C11 C8 N6 C9 0.2(7) . . . . ? S1 C8 N6 C9 176.3(4) . . . . ? C8 N6 C9 C10 -0.1(8) . . . . ? C11 N7 C10 C9 -1.3(9) . . . . ? N6 C9 C10 N7 0.7(9) . . . . ? C10 N7 C11 C8 1.4(9) . . . . ? N6 C8 C11 N7 -0.9(9) . . . . ? S1 C8 C11 N7 -176.9(5) . . . . ? C15 N9 C12 C13 0.0(7) . . . . ? C15 N9 C12 S3 173.0(4) . . . . ? C3 S3 C12 N9 134.3(4) . . . . ? C3 S3 C12 C13 -52.7(4) . . . . ? C14 N8 C13 C12 0.6(8) . . . . ? N9 C12 C13 N8 0.4(8) . . . . ? S3 C12 C13 N8 -172.1(4) . . . . ? C13 N8 C14 C15 -1.9(8) . . . . ? C12 N9 C15 C14 -1.3(9) . . . . ? N8 C14 C15 N9 2.5(10) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.503 _refine_diff_density_min -0.285 _refine_diff_density_rms 0.051 #===End data_compound3 _database_code_depnum_ccdc_archive 'CCDC 704195' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H15 N9 S3' _chemical_formula_weight 453.57 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.5497(11) _cell_length_b 11.0612(15) _cell_length_c 11.5176(16) _cell_angle_alpha 70.183(2) _cell_angle_beta 78.748(3) _cell_angle_gamma 81.825(3) _cell_volume 1001.6(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.504 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 468 _exptl_absorpt_coefficient_mu 0.397 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.935126 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details sadabs _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 P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7021 _diffrn_reflns_av_R_equivalents 0.0214 _diffrn_reflns_av_sigmaI/netI 0.0422 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 28.31 _reflns_number_total 4864 _reflns_number_gt 3737 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0572P)^2^+0.0853P] 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 Constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4864 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0531 _refine_ls_R_factor_gt 0.0392 _refine_ls_wR_factor_ref 0.1096 _refine_ls_wR_factor_gt 0.1011 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _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 S1 S 0.44802(6) 0.04088(4) 0.22442(4) 0.04036(14) Uani 1 1 d . . . S2 S 0.14150(5) -0.04799(4) 0.68475(4) 0.04035(14) Uani 1 1 d . . . S3 S 0.58914(6) -0.38824(4) 0.57581(4) 0.04062(14) Uani 1 1 d . . . N1 N 0.30456(16) -0.01387(13) 0.46287(13) 0.0349(3) Uani 1 1 d . . . N2 N 0.37442(16) -0.21192(13) 0.61696(13) 0.0353(3) Uani 1 1 d . . . N3 N 0.50248(16) -0.16718(13) 0.40472(13) 0.0348(3) Uani 1 1 d . . . N4 N 0.4646(2) 0.27231(18) 0.01683(15) 0.0544(5) Uani 1 1 d . . . N5 N 0.2451(3) 0.48807(19) -0.03180(19) 0.0747(7) Uani 1 1 d . . . N6 N -0.08264(18) -0.06609(16) 0.90533(14) 0.0409(4) Uani 1 1 d . . . N7 N -0.0839(3) -0.24300(19) 1.14519(17) 0.0664(6) Uani 1 1 d . . . N8 N 0.7950(2) -0.60894(16) 0.56649(15) 0.0488(4) Uani 1 1 d . . . N9 N 0.9938(2) -0.66167(17) 0.36335(17) 0.0556(5) Uani 1 1 d . . . C1 C 0.41109(19) -0.05413(16) 0.38078(15) 0.0321(4) Uani 1 1 d . . . C2 C 0.28934(19) -0.09880(16) 0.57996(15) 0.0328(4) Uani 1 1 d . . . C3 C 0.47951(19) -0.24018(16) 0.52372(15) 0.0324(4) Uani 1 1 d . . . C4 C 0.3165(2) 0.18240(17) 0.22683(16) 0.0377(4) Uani 1 1 d . . . H4A H 0.2063 0.1603 0.2483 0.045 Uiso 1 1 calc R . . H4B H 0.3383 0.2146 0.2901 0.045 Uiso 1 1 calc R . . C5 C 0.3391(2) 0.28528(17) 0.10172(16) 0.0380(4) Uani 1 1 d . . . C6 C 0.4794(3) 0.3703(2) -0.0922(2) 0.0633(7) Uani 1 1 d . . . H6A H 0.5659 0.3659 -0.1540 0.076 Uiso 1 1 calc R . . C7 C 0.3710(3) 0.4756(2) -0.1144(2) 0.0627(7) Uani 1 1 d . . . H7A H 0.3869 0.5410 -0.1907 0.075 Uiso 1 1 calc R . . C8 C 0.2301(3) 0.3917(2) 0.0754(2) 0.0606(7) Uani 1 1 d . . . H8A H 0.1417 0.3962 0.1358 0.073 Uiso 1 1 calc R . . C9 C 0.1567(2) -0.18235(18) 0.82564(16) 0.0420(4) Uani 1 1 d . . . H9A H 0.1448 -0.2616 0.8109 0.050 Uiso 1 1 calc R . . H9B H 0.2615 -0.1891 0.8489 0.050 Uiso 1 1 calc R . . C10 C 0.0295(2) -0.16465(17) 0.93011(16) 0.0360(4) Uani 1 1 d . . . C11 C -0.1956(2) -0.0586(2) 1.00237(18) 0.0448(5) Uani 1 1 d . . . H11A H -0.2761 0.0083 0.9894 0.054 Uiso 1 1 calc R . . C12 C -0.1961(3) -0.1463(2) 1.11955(19) 0.0531(5) Uani 1 1 d . . . H12A H -0.2778 -0.1377 1.1833 0.064 Uiso 1 1 calc R . . C13 C 0.0280(3) -0.2510(2) 1.04952(19) 0.0585(6) Uani 1 1 d . . . H13A H 0.1088 -0.3177 1.0636 0.070 Uiso 1 1 calc R . . C14 C 0.7082(2) -0.39619(17) 0.43125(17) 0.0412(4) Uani 1 1 d . . . H14A H 0.6390 -0.3860 0.3705 0.049 Uiso 1 1 calc R . . H14B H 0.7785 -0.3266 0.3983 0.049 Uiso 1 1 calc R . . C15 C 0.8062(2) -0.52344(17) 0.45204(17) 0.0370(4) Uani 1 1 d . . . C16 C 0.8854(3) -0.7213(2) 0.5778(2) 0.0541(6) Uani 1 1 d . . . H16A H 0.8813 -0.7840 0.6560 0.065 Uiso 1 1 calc R . . C17 C 0.9832(3) -0.7461(2) 0.4777(2) 0.0519(5) Uani 1 1 d . . . H17A H 1.0441 -0.8247 0.4904 0.062 Uiso 1 1 calc R . . C18 C 0.9061(2) -0.55131(19) 0.35239(18) 0.0486(5) Uani 1 1 d . . . H18A H 0.9116 -0.4890 0.2739 0.058 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 S1 0.0455(3) 0.0378(2) 0.0257(2) -0.00404(18) 0.00278(17) 0.00841(18) S2 0.0430(3) 0.0358(2) 0.0289(2) -0.00465(18) 0.00548(17) 0.01006(18) S3 0.0457(3) 0.0328(2) 0.0306(2) -0.00426(18) 0.00344(18) 0.00951(18) N1 0.0363(7) 0.0317(7) 0.0282(7) -0.0056(6) 0.0028(6) 0.0031(6) N2 0.0369(7) 0.0317(7) 0.0282(7) -0.0058(6) 0.0033(6) 0.0051(6) N3 0.0378(8) 0.0305(7) 0.0286(7) -0.0060(6) 0.0024(6) 0.0023(6) N4 0.0535(10) 0.0547(11) 0.0357(9) -0.0015(8) 0.0049(7) 0.0084(8) N5 0.0851(14) 0.0451(11) 0.0559(12) 0.0100(9) 0.0152(10) 0.0152(10) N6 0.0381(8) 0.0444(9) 0.0358(8) -0.0128(7) 0.0005(6) 0.0021(6) N7 0.0852(14) 0.0486(11) 0.0391(9) -0.0030(8) 0.0205(9) 0.0094(9) N8 0.0594(10) 0.0409(9) 0.0369(8) -0.0087(7) -0.0033(7) 0.0106(7) N9 0.0586(11) 0.0461(10) 0.0504(10) -0.0152(8) 0.0031(8) 0.0166(8) C1 0.0336(8) 0.0316(8) 0.0258(8) -0.0059(7) -0.0003(6) -0.0004(6) C2 0.0332(8) 0.0320(8) 0.0281(8) -0.0078(7) 0.0017(6) 0.0005(6) C3 0.0322(8) 0.0295(8) 0.0307(8) -0.0073(7) -0.0007(6) 0.0008(6) C4 0.0435(9) 0.0344(9) 0.0274(8) -0.0053(7) -0.0009(7) 0.0043(7) C5 0.0437(10) 0.0332(9) 0.0307(9) -0.0055(7) -0.0005(7) -0.0019(7) C6 0.0608(13) 0.0643(15) 0.0403(11) 0.0007(11) 0.0115(10) 0.0027(11) C7 0.0725(15) 0.0487(13) 0.0402(11) 0.0093(10) 0.0075(10) -0.0005(11) C8 0.0667(14) 0.0417(11) 0.0461(12) 0.0019(9) 0.0139(10) 0.0115(10) C9 0.0422(10) 0.0381(10) 0.0315(9) -0.0041(8) 0.0075(7) 0.0065(8) C10 0.0370(9) 0.0335(9) 0.0322(8) -0.0098(7) 0.0053(7) -0.0033(7) C11 0.0403(10) 0.0494(11) 0.0428(10) -0.0202(9) 0.0020(8) 0.0041(8) C12 0.0588(13) 0.0488(12) 0.0435(11) -0.0182(10) 0.0158(9) -0.0023(10) C13 0.0707(14) 0.0418(11) 0.0407(11) -0.0028(9) 0.0119(10) 0.0126(10) C14 0.0474(10) 0.0321(9) 0.0340(9) -0.0073(7) 0.0042(7) 0.0067(7) C15 0.0366(9) 0.0324(9) 0.0381(9) -0.0115(7) -0.0013(7) 0.0037(7) C16 0.0672(14) 0.0396(11) 0.0437(11) -0.0045(9) -0.0115(10) 0.0150(10) C17 0.0568(12) 0.0383(10) 0.0535(12) -0.0123(9) -0.0124(10) 0.0181(9) C18 0.0544(11) 0.0390(10) 0.0378(10) -0.0060(8) 0.0051(8) 0.0095(8) _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 S1 C1 1.7425(16) . ? S1 C4 1.7981(17) . ? S2 C2 1.7415(16) . ? S2 C9 1.8030(17) . ? S3 C3 1.7428(16) . ? S3 C14 1.7969(18) . ? N1 C1 1.325(2) . ? N1 C2 1.351(2) . ? N2 C2 1.333(2) . ? N2 C3 1.353(2) . ? N3 C3 1.326(2) . ? N3 C1 1.350(2) . ? N4 C5 1.330(2) . ? N4 C6 1.349(2) . ? N5 C7 1.315(3) . ? N5 C8 1.328(3) . ? N6 C10 1.337(2) . ? N6 C11 1.344(2) . ? N7 C12 1.325(3) . ? N7 C13 1.329(2) . ? N8 C15 1.331(2) . ? N8 C16 1.347(2) . ? N9 C18 1.319(2) . ? N9 C17 1.326(3) . ? C4 C5 1.500(2) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C8 1.379(3) . ? C6 C7 1.366(3) . ? C6 H6A 0.9300 . ? C7 H7A 0.9300 . ? C8 H8A 0.9300 . ? C9 C10 1.503(2) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C13 1.382(3) . ? C11 C12 1.369(3) . ? C11 H11A 0.9300 . ? C12 H12A 0.9300 . ? C13 H13A 0.9300 . ? C14 C15 1.502(2) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C18 1.387(2) . ? C16 C17 1.369(3) . ? C16 H16A 0.9300 . ? C17 H17A 0.9300 . ? C18 H18A 0.9300 . ? 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 C1 S1 C4 100.91(8) . . ? C2 S2 C9 100.42(8) . . ? C3 S3 C14 100.52(8) . . ? C1 N1 C2 113.97(14) . . ? C2 N2 C3 113.80(13) . . ? C3 N3 C1 113.76(13) . . ? C5 N4 C6 115.96(17) . . ? C7 N5 C8 115.69(19) . . ? C10 N6 C11 115.91(16) . . ? C12 N7 C13 115.88(18) . . ? C15 N8 C16 115.96(16) . . ? C18 N9 C17 115.72(17) . . ? N1 C1 N3 126.35(14) . . ? N1 C1 S1 121.17(12) . . ? N3 C1 S1 112.48(11) . . ? N2 C2 N1 125.83(14) . . ? N2 C2 S2 120.84(12) . . ? N1 C2 S2 113.33(12) . . ? N3 C3 N2 126.23(14) . . ? N3 C3 S3 121.32(12) . . ? N2 C3 S3 112.46(12) . . ? C5 C4 S1 110.58(12) . . ? C5 C4 H4A 109.5 . . ? S1 C4 H4A 109.5 . . ? C5 C4 H4B 109.5 . . ? S1 C4 H4B 109.5 . . ? H4A C4 H4B 108.1 . . ? N4 C5 C8 120.64(16) . . ? N4 C5 C4 119.32(16) . . ? C8 C5 C4 120.05(16) . . ? N4 C6 C7 121.94(19) . . ? N4 C6 H6A 119.0 . . ? C7 C6 H6A 119.0 . . ? N5 C7 C6 122.45(18) . . ? N5 C7 H7A 118.8 . . ? C6 C7 H7A 118.8 . . ? N5 C8 C5 123.28(19) . . ? N5 C8 H8A 118.4 . . ? C5 C8 H8A 118.4 . . ? C10 C9 S2 110.32(12) . . ? C10 C9 H9A 109.6 . . ? S2 C9 H9A 109.6 . . ? C10 C9 H9B 109.6 . . ? S2 C9 H9B 109.6 . . ? H9A C9 H9B 108.1 . . ? N6 C10 C13 120.92(16) . . ? N6 C10 C9 119.16(15) . . ? C13 C10 C9 119.91(16) . . ? N6 C11 C12 122.22(18) . . ? N6 C11 H11A 118.9 . . ? C12 C11 H11A 118.9 . . ? N7 C12 C11 122.17(18) . . ? N7 C12 H12A 118.9 . . ? C11 C12 H12A 118.9 . . ? N7 C13 C10 122.89(19) . . ? N7 C13 H13A 118.6 . . ? C10 C13 H13A 118.6 . . ? C15 C14 S3 110.09(12) . . ? C15 C14 H14A 109.6 . . ? S3 C14 H14A 109.6 . . ? C15 C14 H14B 109.6 . . ? S3 C14 H14B 109.6 . . ? H14A C14 H14B 108.2 . . ? N8 C15 C18 120.69(16) . . ? N8 C15 C14 119.30(15) . . ? C18 C15 C14 120.02(16) . . ? N8 C16 C17 122.07(18) . . ? N8 C16 H16A 119.0 . . ? C17 C16 H16A 119.0 . . ? N9 C17 C16 122.23(18) . . ? N9 C17 H17A 118.9 . . ? C16 C17 H17A 118.9 . . ? N9 C18 C15 123.33(17) . . ? N9 C18 H18A 118.3 . . ? C15 C18 H18A 118.3 . . ? 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 C2 N1 C1 N3 -1.0(3) . . . . ? C2 N1 C1 S1 179.70(13) . . . . ? C3 N3 C1 N1 -0.9(3) . . . . ? C3 N3 C1 S1 178.51(13) . . . . ? C4 S1 C1 N1 1.68(17) . . . . ? C4 S1 C1 N3 -177.72(14) . . . . ? C3 N2 C2 N1 -2.2(3) . . . . ? C3 N2 C2 S2 177.22(13) . . . . ? C1 N1 C2 N2 2.7(3) . . . . ? C1 N1 C2 S2 -176.81(13) . . . . ? C9 S2 C2 N2 0.38(18) . . . . ? C9 S2 C2 N1 179.89(14) . . . . ? C1 N3 C3 N2 1.4(3) . . . . ? C1 N3 C3 S3 -178.25(13) . . . . ? C2 N2 C3 N3 0.0(3) . . . . ? C2 N2 C3 S3 179.68(13) . . . . ? C14 S3 C3 N3 -1.92(18) . . . . ? C14 S3 C3 N2 178.41(14) . . . . ? C1 S1 C4 C5 174.74(14) . . . . ? C6 N4 C5 C8 2.0(3) . . . . ? C6 N4 C5 C4 -178.3(2) . . . . ? S1 C4 C5 N4 -12.2(2) . . . . ? S1 C4 C5 C8 167.52(18) . . . . ? C5 N4 C6 C7 -0.7(4) . . . . ? C8 N5 C7 C6 0.4(4) . . . . ? N4 C6 C7 N5 -0.5(4) . . . . ? C7 N5 C8 C5 1.0(4) . . . . ? N4 C5 C8 N5 -2.3(4) . . . . ? C4 C5 C8 N5 178.0(2) . . . . ? C2 S2 C9 C10 -175.89(14) . . . . ? C11 N6 C10 C13 -1.0(3) . . . . ? C11 N6 C10 C9 177.91(18) . . . . ? S2 C9 C10 N6 6.7(2) . . . . ? S2 C9 C10 C13 -174.35(18) . . . . ? C10 N6 C11 C12 0.1(3) . . . . ? C13 N7 C12 C11 -1.1(4) . . . . ? N6 C11 C12 N7 1.0(4) . . . . ? C12 N7 C13 C10 0.1(4) . . . . ? N6 C10 C13 N7 1.0(4) . . . . ? C9 C10 C13 N7 -178.0(2) . . . . ? C3 S3 C14 C15 -175.77(14) . . . . ? C16 N8 C15 C18 0.0(3) . . . . ? C16 N8 C15 C14 179.47(19) . . . . ? S3 C14 C15 N8 -0.3(2) . . . . ? S3 C14 C15 C18 179.21(17) . . . . ? C15 N8 C16 C17 0.1(3) . . . . ? C18 N9 C17 C16 1.1(4) . . . . ? N8 C16 C17 N9 -0.7(4) . . . . ? C17 N9 C18 C15 -1.0(3) . . . . ? N8 C15 C18 N9 0.5(4) . . . . ? C14 C15 C18 N9 -179.0(2) . . . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.297 _refine_diff_density_min -0.202 _refine_diff_density_rms 0.055