data_k10cgf1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H15 N O2 S' _chemical_formula_weight 309.37 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' 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' N N 0.0061 0.0033 '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/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 12.0800(2) _cell_length_b 6.5760(1) _cell_length_c 19.2930(4) _cell_angle_alpha 90.00 _cell_angle_beta 104.500(1) _cell_angle_gamma 90.00 _cell_volume 1483.78(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 18315 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _exptl_crystal_description tabloid _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.385 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.225 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.882 _exptl_absorpt_correction_T_max 0.937 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_device_type '95mm CCD camera on \k-goniostat' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24599 _diffrn_reflns_av_R_equivalents 0.0457 _diffrn_reflns_av_sigmaI/netI 0.0320 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.55 _diffrn_reflns_theta_max 27.46 _reflns_number_total 3390 _reflns_number_gt 2802 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo & Scalepack (Otwinowski, Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick 1990)' _computing_structure_refinement 'SHELXL-97/2 (Sheldrick 1997)' _computing_molecular_graphics 'ORTEX (P.McArdle 1995)' _computing_publication_material 'SHELXL-97/2 (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^)+(0.0460P)^2^+0.6748P] 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 3390 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0506 _refine_ls_R_factor_gt 0.0391 _refine_ls_wR_factor_ref 0.1002 _refine_ls_wR_factor_gt 0.0941 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _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 0.48580(3) -0.14620(6) 0.298901(19) 0.02224(12) Uani 1 1 d . . . O1 O 0.38207(9) -0.02991(18) 0.28825(6) 0.0306(3) Uani 1 1 d . . . O2 O 0.49492(10) -0.33448(17) 0.33800(6) 0.0289(3) Uani 1 1 d . . . N1 N 0.68393(12) -0.6275(2) 0.06749(7) 0.0300(3) Uani 1 1 d . . . C1 C 0.60134(12) 0.0092(2) 0.34264(7) 0.0210(3) Uani 1 1 d . . . C2 C 0.58062(13) 0.2081(2) 0.35976(8) 0.0253(3) Uani 1 1 d . . . H2 H 0.5062 0.2648 0.3441 0.030 Uiso 1 1 calc R . . C3 C 0.67024(14) 0.3232(2) 0.40014(8) 0.0281(3) Uani 1 1 d . . . H3 H 0.6562 0.4586 0.4128 0.034 Uiso 1 1 calc R . . C4 C 0.78007(14) 0.2440(3) 0.42233(8) 0.0286(4) Uani 1 1 d . . . C5 C 0.79922(13) 0.0455(3) 0.40236(9) 0.0300(4) Uani 1 1 d . . . H5 H 0.8743 -0.0092 0.4161 0.036 Uiso 1 1 calc R . . C6 C 0.71127(13) -0.0730(3) 0.36308(8) 0.0270(3) Uani 1 1 d . . . H6 H 0.7253 -0.2082 0.3502 0.032 Uiso 1 1 calc R . . C7 C 0.87580(16) 0.3706(3) 0.46644(10) 0.0389(4) Uani 1 1 d . . . H7A H 0.9137 0.4443 0.4347 0.058 Uiso 1 1 calc R . . H7B H 0.9312 0.2820 0.4983 0.058 Uiso 1 1 calc R . . H7C H 0.8448 0.4682 0.4951 0.058 Uiso 1 1 calc R . . C8 C 0.51068(12) -0.2015(2) 0.21442(8) 0.0224(3) Uani 1 1 d . . . C9 C 0.46659(13) -0.0730(2) 0.15694(8) 0.0249(3) Uani 1 1 d . . . H9 H 0.4237 0.0443 0.1624 0.030 Uiso 1 1 calc R . . C10 C 0.48719(13) -0.1214(2) 0.09127(8) 0.0269(3) Uani 1 1 d . . . H10 H 0.4577 -0.0363 0.0511 0.032 Uiso 1 1 calc R . . C11 C 0.55017(13) -0.2924(3) 0.08354(8) 0.0254(3) Uani 1 1 d . . . H11 H 0.5627 -0.3231 0.0380 0.031 Uiso 1 1 calc R . . C12 C 0.59560(12) -0.4204(2) 0.14155(8) 0.0222(3) Uani 1 1 d . . . C13 C 0.57473(12) -0.3727(2) 0.20771(8) 0.0228(3) Uani 1 1 d . . . H13 H 0.6043 -0.4571 0.2481 0.027 Uiso 1 1 calc R . . C14 C 0.66333(12) -0.6047(2) 0.13249(8) 0.0234(3) Uani 1 1 d . . . C15 C 0.70351(13) -0.7433(2) 0.18767(9) 0.0278(3) Uani 1 1 d . . . H15 H 0.6874 -0.7242 0.2330 0.033 Uiso 1 1 calc R . . C16 C 0.76720(14) -0.9090(3) 0.17595(9) 0.0327(4) Uani 1 1 d . . . H16 H 0.7958 -1.0045 0.2131 0.039 Uiso 1 1 calc R . . C17 C 0.78839(14) -0.9330(3) 0.10926(10) 0.0335(4) Uani 1 1 d . . . H17 H 0.8316 -1.0453 0.0995 0.040 Uiso 1 1 calc R . . C18 C 0.74525(14) -0.7900(3) 0.05730(9) 0.0332(4) Uani 1 1 d . . . H18 H 0.7598 -0.8074 0.0115 0.040 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 0.0221(2) 0.0232(2) 0.0226(2) -0.00131(14) 0.00776(14) -0.00006(14) O1 0.0228(6) 0.0369(7) 0.0324(6) -0.0046(5) 0.0076(4) 0.0051(5) O2 0.0360(6) 0.0243(6) 0.0294(6) 0.0010(5) 0.0140(5) -0.0037(5) N1 0.0290(7) 0.0359(8) 0.0256(7) -0.0062(6) 0.0077(5) 0.0022(6) C1 0.0235(7) 0.0232(7) 0.0175(7) 0.0001(6) 0.0074(5) -0.0014(6) C2 0.0281(8) 0.0241(8) 0.0246(8) 0.0012(6) 0.0084(6) 0.0032(6) C3 0.0366(9) 0.0231(8) 0.0260(8) -0.0031(6) 0.0105(7) -0.0029(7) C4 0.0292(8) 0.0375(10) 0.0215(7) -0.0043(7) 0.0113(6) -0.0078(7) C5 0.0223(8) 0.0404(10) 0.0286(8) -0.0036(7) 0.0089(6) 0.0017(7) C6 0.0269(8) 0.0277(8) 0.0279(8) -0.0029(7) 0.0099(6) 0.0036(6) C7 0.0353(9) 0.0515(12) 0.0312(9) -0.0132(8) 0.0111(7) -0.0136(8) C8 0.0207(7) 0.0246(8) 0.0219(7) -0.0028(6) 0.0051(6) -0.0028(6) C9 0.0229(7) 0.0241(8) 0.0272(8) 0.0003(6) 0.0055(6) 0.0010(6) C10 0.0273(8) 0.0296(9) 0.0226(8) 0.0038(6) 0.0040(6) 0.0001(6) C11 0.0236(7) 0.0312(8) 0.0222(7) -0.0008(6) 0.0071(6) -0.0036(6) C12 0.0187(7) 0.0241(8) 0.0238(7) -0.0023(6) 0.0053(6) -0.0030(6) C13 0.0229(7) 0.0236(8) 0.0213(7) -0.0004(6) 0.0041(6) -0.0011(6) C14 0.0186(7) 0.0263(8) 0.0252(7) -0.0062(6) 0.0057(6) -0.0047(6) C15 0.0287(8) 0.0263(8) 0.0303(8) -0.0024(7) 0.0108(6) -0.0018(6) C16 0.0296(9) 0.0282(9) 0.0403(10) -0.0002(7) 0.0085(7) 0.0024(7) C17 0.0259(8) 0.0315(9) 0.0435(10) -0.0106(8) 0.0092(7) 0.0020(7) C18 0.0288(8) 0.0423(10) 0.0295(8) -0.0098(8) 0.0090(7) 0.0032(7) _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 O1 1.4381(11) . ? S1 O2 1.4396(12) . ? S1 C1 1.7647(15) . ? S1 C8 1.7676(15) . ? N1 C18 1.342(2) . ? N1 C14 1.347(2) . ? C1 C2 1.387(2) . ? C1 C6 1.396(2) . ? C2 C3 1.389(2) . ? C2 H2 0.9500 . ? C3 C4 1.389(2) . ? C3 H3 0.9500 . ? C4 C5 1.397(2) . ? C4 C7 1.504(2) . ? C5 C6 1.381(2) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C9 1.390(2) . ? C8 C13 1.390(2) . ? C9 C10 1.388(2) . ? C9 H9 0.9500 . ? C10 C11 1.386(2) . ? C10 H10 0.9500 . ? C11 C12 1.398(2) . ? C11 H11 0.9500 . ? C12 C13 1.397(2) . ? C12 C14 1.497(2) . ? C13 H13 0.9500 . ? C14 C15 1.393(2) . ? C15 C16 1.385(2) . ? C15 H15 0.9500 . ? C16 C17 1.382(2) . ? C16 H16 0.9500 . ? C17 C18 1.378(3) . ? C17 H17 0.9500 . ? C18 H18 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 O1 S1 O2 118.81(7) . . ? O1 S1 C1 108.48(7) . . ? O2 S1 C1 107.45(7) . . ? O1 S1 C8 108.72(7) . . ? O2 S1 C8 107.33(7) . . ? C1 S1 C8 105.26(7) . . ? C18 N1 C14 117.54(14) . . ? C2 C1 C6 120.88(14) . . ? C2 C1 S1 119.44(12) . . ? C6 C1 S1 119.58(12) . . ? C1 C2 C3 119.05(15) . . ? C1 C2 H2 120.5 . . ? C3 C2 H2 120.5 . . ? C2 C3 C4 121.25(15) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C3 C4 C5 118.46(15) . . ? C3 C4 C7 120.44(16) . . ? C5 C4 C7 121.10(16) . . ? C6 C5 C4 121.39(15) . . ? C6 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? C5 C6 C1 118.92(15) . . ? C5 C6 H6 120.5 . . ? C1 C6 H6 120.5 . . ? C4 C7 H7A 109.5 . . ? C4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C9 C8 C13 121.94(14) . . ? C9 C8 S1 119.41(12) . . ? C13 C8 S1 118.65(11) . . ? C10 C9 C8 117.93(14) . . ? C10 C9 H9 121.0 . . ? C8 C9 H9 121.0 . . ? C11 C10 C9 120.86(14) . . ? C11 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? C10 C11 C12 121.22(14) . . ? C10 C11 H11 119.4 . . ? C12 C11 H11 119.4 . . ? C13 C12 C11 118.12(14) . . ? C13 C12 C14 121.17(13) . . ? C11 C12 C14 120.70(13) . . ? C8 C13 C12 119.93(14) . . ? C8 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? N1 C14 C15 121.92(14) . . ? N1 C14 C12 115.64(14) . . ? C15 C14 C12 122.44(13) . . ? C16 C15 C14 119.44(15) . . ? C16 C15 H15 120.3 . . ? C14 C15 H15 120.3 . . ? C17 C16 C15 118.80(16) . . ? C17 C16 H16 120.6 . . ? C15 C16 H16 120.6 . . ? C18 C17 C16 118.33(16) . . ? C18 C17 H17 120.8 . . ? C16 C17 H17 120.8 . . ? N1 C18 C17 123.98(15) . . ? N1 C18 H18 118.0 . . ? C17 C18 H18 118.0 . . ? 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 O1 S1 C1 C2 -0.34(14) . . . . ? O2 S1 C1 C2 -129.95(12) . . . . ? C8 S1 C1 C2 115.88(12) . . . . ? O1 S1 C1 C6 176.07(12) . . . . ? O2 S1 C1 C6 46.46(13) . . . . ? C8 S1 C1 C6 -67.70(13) . . . . ? C6 C1 C2 C3 -2.4(2) . . . . ? S1 C1 C2 C3 173.92(11) . . . . ? C1 C2 C3 C4 1.2(2) . . . . ? C2 C3 C4 C5 0.8(2) . . . . ? C2 C3 C4 C7 -179.59(14) . . . . ? C3 C4 C5 C6 -1.7(2) . . . . ? C7 C4 C5 C6 178.69(15) . . . . ? C4 C5 C6 C1 0.5(2) . . . . ? C2 C1 C6 C5 1.6(2) . . . . ? S1 C1 C6 C5 -174.79(12) . . . . ? O1 S1 C8 C9 26.10(14) . . . . ? O2 S1 C8 C9 155.79(12) . . . . ? C1 S1 C8 C9 -89.96(13) . . . . ? O1 S1 C8 C13 -154.27(12) . . . . ? O2 S1 C8 C13 -24.57(14) . . . . ? C1 S1 C8 C13 89.67(13) . . . . ? C13 C8 C9 C10 0.7(2) . . . . ? S1 C8 C9 C10 -179.66(12) . . . . ? C8 C9 C10 C11 -0.2(2) . . . . ? C9 C10 C11 C12 -0.5(2) . . . . ? C10 C11 C12 C13 0.7(2) . . . . ? C10 C11 C12 C14 179.93(14) . . . . ? C9 C8 C13 C12 -0.5(2) . . . . ? S1 C8 C13 C12 179.87(11) . . . . ? C11 C12 C13 C8 -0.2(2) . . . . ? C14 C12 C13 C8 -179.44(13) . . . . ? C18 N1 C14 C15 0.0(2) . . . . ? C18 N1 C14 C12 179.46(14) . . . . ? C13 C12 C14 N1 -175.89(13) . . . . ? C11 C12 C14 N1 4.9(2) . . . . ? C13 C12 C14 C15 3.6(2) . . . . ? C11 C12 C14 C15 -175.63(14) . . . . ? N1 C14 C15 C16 0.4(2) . . . . ? C12 C14 C15 C16 -179.02(14) . . . . ? C14 C15 C16 C17 -0.5(2) . . . . ? C15 C16 C17 C18 0.2(2) . . . . ? C14 N1 C18 C17 -0.3(2) . . . . ? C16 C17 C18 N1 0.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.294 _refine_diff_density_min -0.421 _refine_diff_density_rms 0.054