# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 1999 # CCDC Number: 207/360 #cmex2 is compound 1j in the paper #cmex5 is compound 1m in the paper data_cmex2 #------------------------------------------------------------------------------ _publ_section_references ; Molecular Structure Corporation. (1992-1997). teXsan. Single Crystal Structure Analysis Software. Version 1.7. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. North, A.C.T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359. Zachariasen, W. H. (1967). Acta Cryst. 23, 558-564. Sheldrick, G.M. (1985). In: "Crystallographic Computing 3" (Eds G.M. Sheldrick, C. Kruger and R. Goddard) Oxford University Press, pp. 175-189. ; #------------------------------------------------------------------------------ _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan (MSC, 1992-1997)' _computing_structure_solution ; SHELXS86 (Sheldrick, 1985) ; _computing_structure_refinement 'teXsan (MSC, 1992-1997)' _computing_publication_material 'teXsan (MSC, 1992-1997)' #------------------------------------------------------------------------------ _cell_length_a 18.514(2) _cell_length_b 7.606(2) _cell_length_c 12.166(1) _cell_angle_alpha 90 _cell_angle_beta 105.58(1) _cell_angle_gamma 90 _cell_volume 1650.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293.2 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 36.8 _cell_measurement_theta_max 37.5 #------------------------------------------------------------------------------ _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c ' _symmetry_Int_Tables_number 14 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' #------------------------------------------------------------------------------ _publ_section_exptl_prep ; ENTER EXPERIMENTAL SECTION ; _exptl_crystal_description 'plate' _exptl_crystal_colour 'clear' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.221 _exptl_crystal_density_meas 'not measured' _chemical_formula_weight 303.40 _chemical_formula_analytical 'C21 H21 N O ' _chemical_formula_sum 'C21 H21 N O ' _chemical_formula_moiety 'C21 H21 N O ' _chemical_formula_structural 'C21 H21 N O ' _chemical_compound_source - _exptl_crystal_F_000 648.00 _exptl_absorpt_coefficient_mu 0.577 _exptl_absorpt_correction_type ; \y scans (North,Phillips & Matthews, 1968) ; _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.682 _exptl_special_details ; The scan width was (1.10+0.35tan\q)\% with an \w scan speed of 0\% per minute (up to 5 scans to achieve I/\s(I) > 15). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1. ; #------------------------------------------------------------------------------ _diffrn_special_details ; ? ; _diffrn_ambient_temperature 293.2 _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device_type 'Rigaku AFC7S' _diffrn_measurement_method \w _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% -0.38 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 6 -1 -2 6 -1 -1 6 1 -1 _diffrn_reflns_number 2767 _reflns_number_total 2676 _reflns_number_gt 1942 _reflns_threshold_expression I>3.00\s(I) _diffrn_reflns_av_R_equivalents 0.05893 _diffrn_reflns_av_sigmaI/netI 0.030 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.77 _diffrn_reflns_theta_max 60.04 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 0.04798 _diffrn_orient_matrix_UB_12 -0.06737 _diffrn_orient_matrix_UB_13 0.02554 _diffrn_orient_matrix_UB_21 -0.02874 _diffrn_orient_matrix_UB_22 -0.10784 _diffrn_orient_matrix_UB_23 0.00913 _diffrn_orient_matrix_UB_31 -0.00398 _diffrn_orient_matrix_UB_32 -0.03344 _diffrn_orient_matrix_UB_33 -0.08091 #------------------------------------------------------------------------------ loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 84 0.017 0.009 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H 0 84 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; N 0 4 0.029 0.018 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; O 0 4 0.047 0.032 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_refinement_flags _atom_site_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom O(9) 0.19822(8) 0.2515(2) -0.0108(1) 0.0629(5) 1.000 . Uani d ? N(9) 0.2497(1) 0.3225(3) -0.0673(2) 0.0599(7) 1.000 . Uani d ? C(1) 0.4467(1) 0.2428(3) -0.0230(2) 0.0562(8) 1.000 . Uani d ? C(1A) 0.5095(1) 0.2884(3) -0.0625(2) 0.0515(7) 1.000 . Uani d ? C(2) 0.3756(1) 0.2943(3) -0.0785(2) 0.0550(8) 1.000 . Uani d ? C(3) 0.3642(1) 0.3939(3) -0.1803(2) 0.0639(8) 1.000 . Uani d ? C(4) 0.4234(1) 0.4408(3) -0.2199(2) 0.0624(8) 1.000 . Uani d ? C(4A) 0.4976(1) 0.3905(3) -0.1630(2) 0.0542(7) 1.000 . Uani d ? C(5) 0.5603(1) 0.4380(3) -0.2021(2) 0.0631(8) 1.000 . Uani d ? C(6) 0.6305(1) 0.3868(4) -0.1456(2) 0.0686(9) 1.000 . Uani d ? C(7) 0.6420(1) 0.2868(4) -0.0464(2) 0.0698(9) 1.000 . Uani d ? C(8) 0.5832(1) 0.2384(3) -0.0053(2) 0.0621(8) 1.000 . Uani d ? C(9) 0.3134(1) 0.2498(3) -0.0307(2) 0.0598(8) 1.000 . Uani d ? C(10) 0.1369(1) 0.3743(3) -0.0203(2) 0.0580(8) 1.000 . Uani d ? C(11) 0.0697(1) 0.2662(3) -0.0147(2) 0.0624(8) 1.000 . Uani d ? C(12) 0.0429(1) 0.1363(3) -0.1114(2) 0.0661(8) 1.000 . Uani d ? C(13) 0.0115(2) 0.2214(4) -0.2263(2) 0.083(1) 1.000 . Uani d ? C(14) 0.1587(1) 0.5124(3) 0.0726(2) 0.0541(8) 1.000 . Uani d ? C(15) 0.1831(1) 0.4657(3) 0.1867(2) 0.0621(8) 1.000 . Uani d ? C(16) 0.2024(1) 0.5912(4) 0.2713(2) 0.0677(9) 1.000 . Uani d ? C(17) 0.1986(1) 0.7680(4) 0.2424(2) 0.0691(9) 1.000 . Uani d ? C(18) 0.1748(1) 0.8155(3) 0.1297(2) 0.0707(9) 1.000 . Uani d ? C(19) 0.1544(1) 0.6900(3) 0.0446(2) 0.0618(8) 1.000 . Uani d ? H(1) 0.4542 0.1741 0.0443 0.067 1.000 . Uiso c ? H(3) 0.3149 0.4279 -0.2209 0.077 1.000 . Uiso c ? H(4) 0.4147 0.5092 -0.2876 0.075 1.000 . Uiso c ? H(5) 0.5531 0.5070 -0.2693 0.076 1.000 . Uiso c ? H(6) 0.6719 0.4190 -0.1735 0.082 1.000 . Uiso c ? H(7) 0.6914 0.2520 -0.0068 0.084 1.000 . Uiso c ? H(8) 0.5921 0.1703 0.0625 0.074 1.000 . Uiso c ? H(9) 0.3208 0.1652 0.0286 0.072 1.000 . Uiso c ? H(10) 0.1265 0.4307 -0.0926 0.070 1.000 . Uiso c ? H(11a) 0.0296 0.3446 -0.0153 0.075 1.000 . Uiso c ? H(11b) 0.0824 0.2024 0.0550 0.075 1.000 . Uiso c ? H(12a) 0.0048 0.0654 -0.0950 0.079 1.000 . Uiso c ? H(12b) 0.0841 0.0644 -0.1153 0.079 1.000 . Uiso c ? H(13c) -0.0028 0.1329 -0.2832 0.099 1.000 . Uiso c ? H(13a) 0.0486 0.2947 -0.2434 0.099 1.000 . Uiso c ? H(13b) -0.0311 0.2902 -0.2248 0.099 1.000 . Uiso c ? H(15) 0.1866 0.3448 0.2071 0.075 1.000 . Uiso c ? H(16) 0.2183 0.5567 0.3491 0.081 1.000 . Uiso c ? H(17) 0.2123 0.8553 0.3001 0.083 1.000 . Uiso c ? H(18) 0.1722 0.9366 0.1098 0.085 1.000 . Uiso c ? H(19) 0.1375 0.7252 -0.0329 0.074 1.000 . Uiso c ? loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(9) 0.070(1) 0.045(1) 0.083(1) 0.0024(8) 0.0373(9) 0.0026(9) N(9) 0.070(1) 0.050(1) 0.069(1) -0.002(1) 0.035(1) -0.003(1) C(1) 0.075(2) 0.042(1) 0.057(1) -0.001(1) 0.026(1) 0.000(1) C(1A) 0.067(2) 0.040(1) 0.052(1) -0.001(1) 0.024(1) -0.007(1) C(2) 0.068(2) 0.045(1) 0.058(2) 0.003(1) 0.026(1) -0.004(1) C(3) 0.073(2) 0.057(2) 0.066(2) 0.012(1) 0.026(1) 0.001(1) C(4) 0.087(2) 0.050(2) 0.058(2) 0.008(1) 0.032(1) 0.003(1) C(4A) 0.072(2) 0.040(1) 0.056(1) -0.001(1) 0.027(1) -0.007(1) C(5) 0.088(2) 0.048(2) 0.063(2) -0.005(1) 0.037(1) -0.005(1) C(6) 0.077(2) 0.065(2) 0.073(2) -0.012(2) 0.038(2) -0.013(2) C(7) 0.067(2) 0.069(2) 0.076(2) -0.002(1) 0.024(1) -0.009(2) C(8) 0.073(2) 0.055(2) 0.062(2) 0.000(1) 0.023(1) -0.001(1) C(9) 0.070(2) 0.047(2) 0.067(2) 0.001(1) 0.028(1) -0.001(1) C(10) 0.064(2) 0.048(1) 0.066(2) 0.003(1) 0.026(1) 0.000(1) C(11) 0.071(2) 0.052(2) 0.069(2) -0.003(1) 0.028(1) -0.002(1) C(12) 0.078(2) 0.054(2) 0.069(2) -0.005(1) 0.025(1) 0.000(1) C(13) 0.102(2) 0.068(2) 0.076(2) -0.010(2) 0.021(2) -0.002(2) C(14) 0.061(2) 0.045(1) 0.062(2) -0.001(1) 0.026(1) -0.002(1) C(15) 0.078(2) 0.044(1) 0.068(2) -0.003(1) 0.027(1) 0.002(1) C(16) 0.085(2) 0.062(2) 0.060(2) -0.005(2) 0.026(1) -0.003(1) C(17) 0.081(2) 0.058(2) 0.076(2) -0.008(2) 0.035(2) -0.016(2) C(18) 0.089(2) 0.042(2) 0.089(2) -0.001(1) 0.036(2) -0.001(2) C(19) 0.075(2) 0.048(2) 0.067(2) 0.003(1) 0.027(1) 0.007(1) #------------------------------------------------------------------------------ _refine_special_details ; ? ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme 'w = 1/[\s^2^(Fo) + 0.00000|Fo|^2^]' _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method 'Zachariasen (1967)' _refine_ls_extinction_coef 0.0000109(2) _refine_ls_extinction_expression 'equ(3) Acta Cryst.(1968) A24, p213.' _refine_ls_abs_structure_details - _refine_ls_abs_structure_Flack - _refine_ls_number_reflns 1942 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.0465 _refine_ls_R_factor_gt 0.0465 _refine_ls_wR_factor_all 0.0352 _refine_ls_wR_factor_ref 0.0352 _refine_ls_goodness_of_fit_all 4.502 _refine_ls_goodness_of_fit_ref 4.502 _refine_ls_shift/esd_max 0.0240 _refine_ls_shift/esd_mean 0.0310 _refine_diff_density_min -0.19 _refine_diff_density_max 0.13 #------------------------------------------------------------------------------ _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O(9) N(9) 1.422(2) . . yes O(9) C(10) 1.451(2) . . yes N(9) C(9) 1.271(3) . . yes C(1) C(1A) 1.415(3) . . yes C(1) C(2) 1.365(3) . . yes C(1) H(1) 0.95 . . no C(1A) C(4A) 1.415(3) . . yes C(1A) C(8) 1.409(3) . . yes C(2) C(3) 1.418(3) . . yes C(2) C(9) 1.461(3) . . yes C(3) C(4) 1.359(3) . . yes C(3) H(3) 0.95 . . no C(4) C(4A) 1.416(3) . . yes C(4) H(4) 0.95 . . no C(4A) C(5) 1.415(3) . . yes C(5) C(6) 1.353(3) . . yes C(5) H(5) 0.95 . . no C(6) C(7) 1.394(3) . . yes C(6) H(6) 0.95 . . no C(7) C(8) 1.365(3) . . yes C(7) H(7) 0.95 . . no C(8) H(8) 0.95 . . no C(9) H(9) 0.95 . . no C(10) C(11) 1.508(3) . . yes C(10) C(14) 1.516(3) . . yes C(10) H(10) 0.95 . . no C(11) C(12) 1.514(3) . . yes C(11) H(11a) 0.95 . . no C(11) H(11b) 0.95 . . no C(12) C(13) 1.508(3) . . yes C(12) H(12a) 0.95 . . no C(12) H(12b) 0.95 . . no C(13) H(13c) 0.95 . . no C(13) H(13a) 0.95 . . no C(13) H(13b) 0.95 . . no C(14) C(15) 1.386(3) . . yes C(14) C(19) 1.390(3) . . yes C(15) C(16) 1.378(3) . . yes C(15) H(15) 0.95 . . no C(16) C(17) 1.387(3) . . yes C(16) H(16) 0.95 . . no C(17) C(18) 1.370(3) . . yes C(17) H(17) 0.95 . . no C(18) C(19) 1.385(3) . . yes C(18) H(18) 0.95 . . no C(19) H(19) 0.95 . . no #------------------------------------------------------------------------------ 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N(9) O(9) C(10) 109.1(2) . . . yes O(9) N(9) C(9) 110.2(2) . . . yes C(1A) C(1) C(2) 122.2(2) . . . yes C(1A) C(1) H(1) 118.9 . . . no C(2) C(1) H(1) 118.9 . . . no C(1) C(1A) C(4A) 118.5(2) . . . yes C(1) C(1A) C(8) 122.8(2) . . . yes C(4A) C(1A) C(8) 118.7(2) . . . yes C(1) C(2) C(3) 118.9(2) . . . yes C(1) C(2) C(9) 119.6(2) . . . yes C(3) C(2) C(9) 121.5(2) . . . yes C(2) C(3) C(4) 120.4(2) . . . yes C(2) C(3) H(3) 119.8 . . . no C(4) C(3) H(3) 119.8 . . . no C(3) C(4) C(4A) 121.7(2) . . . yes C(3) C(4) H(4) 119.2 . . . no C(4A) C(4) H(4) 119.2 . . . no C(1A) C(4A) C(4) 118.4(2) . . . yes C(1A) C(4A) C(5) 118.7(2) . . . yes C(4) C(4A) C(5) 122.9(2) . . . yes C(4A) C(5) C(6) 121.2(2) . . . yes C(4A) C(5) H(5) 119.4 . . . no C(6) C(5) H(5) 119.4 . . . no C(5) C(6) C(7) 120.0(2) . . . yes C(5) C(6) H(6) 120.0 . . . no C(7) C(6) H(6) 120.0 . . . no C(6) C(7) C(8) 120.8(2) . . . yes C(6) C(7) H(7) 119.6 . . . no C(8) C(7) H(7) 119.6 . . . no C(1A) C(8) C(7) 120.6(2) . . . yes C(1A) C(8) H(8) 119.7 . . . no C(7) C(8) H(8) 119.7 . . . no N(9) C(9) C(2) 121.1(2) . . . yes N(9) C(9) H(9) 119.4 . . . no C(2) C(9) H(9) 119.5 . . . no O(9) C(10) C(11) 106.4(2) . . . yes O(9) C(10) C(14) 109.9(2) . . . yes O(9) C(10) H(10) 108.9 . . . no C(11) C(10) C(14) 113.7(2) . . . yes C(11) C(10) H(10) 108.9 . . . no C(14) C(10) H(10) 108.9 . . . no C(10) C(11) C(12) 115.0(2) . . . yes C(10) C(11) H(11a) 108.1 . . . no C(10) C(11) H(11b) 108.1 . . . no C(12) C(11) H(11a) 108.1 . . . no C(12) C(11) H(11b) 108.1 . . . no H(11a) C(11) H(11b) 109.4 . . . no C(11) C(12) C(13) 113.9(2) . . . yes C(11) C(12) H(12a) 108.3 . . . no C(11) C(12) H(12b) 108.3 . . . no C(13) C(12) H(12a) 108.4 . . . no C(13) C(12) H(12b) 108.4 . . . no H(12a) C(12) H(12b) 109.5 . . . no C(12) C(13) H(13c) 109.4 . . . no C(12) C(13) H(13a) 109.5 . . . no C(12) C(13) H(13b) 109.5 . . . no H(13c) C(13) H(13a) 109.5 . . . no H(13c) C(13) H(13b) 109.5 . . . no H(13a) C(13) H(13b) 109.5 . . . no C(10) C(14) C(15) 121.3(2) . . . yes C(10) C(14) C(19) 120.3(2) . . . yes C(15) C(14) C(19) 118.4(2) . . . yes C(14) C(15) C(16) 121.3(2) . . . yes C(14) C(15) H(15) 119.4 . . . no C(16) C(15) H(15) 119.3 . . . no C(15) C(16) C(17) 119.8(2) . . . yes C(15) C(16) H(16) 120.1 . . . no C(17) C(16) H(16) 120.1 . . . no C(16) C(17) C(18) 119.3(2) . . . yes C(16) C(17) H(17) 120.3 . . . no C(18) C(17) H(17) 120.3 . . . no C(17) C(18) C(19) 121.1(2) . . . yes C(17) C(18) H(18) 119.5 . . . no C(19) C(18) H(18) 119.5 . . . no C(14) C(19) C(18) 120.1(2) . . . yes C(14) C(19) H(19) 120.0 . . . no C(18) C(19) H(19) 120.0 . . . no #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag C(1) C(4A) 3.564(3) . 3_665 no C(2) C(7) 3.582(3) . 3_665 no C(3) C(8) 3.562(4) . 3_665 no C(6) C(9) 3.481(3) . 3_665 no #------------------------------------------------------------------------------ data_cmex5 #------------------------------------------------------------------------------ _publ_section_references ; Molecular Structure Corporation. (1992-1997). teXsan. Single Crystal Structure Analysis Software. Version 1.7. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. Walker, N. & Stuart. D. (1983). Acta Cryst. A39, 158-166. Zachariasen, W. H. (1967). Acta Cryst. 23, 558-564. Altomare, A., Cascarano, M., Giacovazzo, C., Guagliardi, A. (1993). J. Appl. Cryst., 26, 343. ; #------------------------------------------------------------------------------ _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan (MSC, 1992-1997)' _computing_structure_solution ; SIR92 (Altomare, et. al. 1993) ; _computing_structure_refinement 'teXsan (MSC, 1992-1997)' _computing_publication_material 'teXsan (MSC, 1992-1997)' #------------------------------------------------------------------------------ _cell_length_a 9.087(3) _cell_length_b 7.841(4) _cell_length_c 10.648(3) _cell_angle_alpha 90 _cell_angle_beta 111.95(2) _cell_angle_gamma 90 _cell_volume 703.6(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293.2 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 33.2 _cell_measurement_theta_max 36.5 #------------------------------------------------------------------------------ _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21 ' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' ' -x,1/2+y, -z' #------------------------------------------------------------------------------ _publ_section_exptl_prep ; ENTER EXPERIMENTAL SECTION ; _exptl_crystal_description 'prism' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.229 _exptl_crystal_density_meas 'not measured' _chemical_formula_weight 260.35 _chemical_formula_analytical 'C14 H16 N2 O S ' _chemical_formula_sum 'C14 H16 N2 O S ' _chemical_formula_moiety 'C14 H16 N2 O S ' _chemical_formula_structural 'C14 H16 N2 O S ' _chemical_compound_source - _exptl_crystal_F_000 276.00 _exptl_absorpt_coefficient_mu 1.958 _exptl_absorpt_correction_type ; \DF (DIFABS; Walker & Stuart, 1983) ; _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.540 _exptl_special_details ; The scan width was (1.26+0.35tan\q)\% with an \w scan speed of 16\% per minute (up to 5 scans to achieve I/\s(I) > 12). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1. ; #------------------------------------------------------------------------------ _diffrn_special_details ; ? ; _diffrn_ambient_temperature 293.2 _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device_type 'Rigaku AFC7S' _diffrn_measurement_method \w _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% -1.56 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 0 2 -2 -3 1 1 -2 1 -2 _diffrn_reflns_number 1226 _reflns_number_total 1148 _reflns_number_gt 839 _reflns_threshold_expression I>3.00\s(I) _diffrn_reflns_av_R_equivalents 0.15314 _diffrn_reflns_av_sigmaI/netI 0.040 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 4.47 _diffrn_reflns_theta_max 60.11 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 -0.09183 _diffrn_orient_matrix_UB_12 0.03261 _diffrn_orient_matrix_UB_13 -0.08371 _diffrn_orient_matrix_UB_21 -0.07510 _diffrn_orient_matrix_UB_22 -0.04357 _diffrn_orient_matrix_UB_23 0.04129 _diffrn_orient_matrix_UB_31 -0.00241 _diffrn_orient_matrix_UB_32 0.11535 _diffrn_orient_matrix_UB_33 0.03926 #------------------------------------------------------------------------------ loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 28 0.017 0.009 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H 0 32 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; N 0 4 0.029 0.018 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; O 0 2 0.047 0.032 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; S 0 2 0.319 0.557 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_refinement_flags _atom_site_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom S(1) 0.42171(9) 0.396(1) -0.03428(8) 0.1080(3) 1.000 . Uani d ? O(8) 0.0025(2) 0.209(1) -0.3730(2) 0.0772(7) 1.000 . Uani d ? N(3) 0.5407(3) 0.302(1) -0.2036(3) 0.099(1) 1.000 . Uani d ? N(7) 0.1350(3) 0.248(1) -0.2605(2) 0.0732(7) 1.000 . Uani d ? C(2) 0.4075(3) 0.315(1) -0.1876(3) 0.0763(8) 1.000 . Uani d ? C(4) 0.6588(4) 0.359(1) -0.0938(4) 0.114(1) 1.000 . Uani d ? C(5) 0.6229(4) 0.413(1) 0.0104(3) 0.102(1) 1.000 . Uani d ? C(6) 0.2575(3) 0.261(1) -0.2895(3) 0.0756(9) 1.000 . Uani d ? C(9) -0.1216(4) 0.148(1) -0.3322(3) 0.0721(8) 1.000 . Uani d ? C(10) -0.0857(3) -0.030(1) -0.2712(2) 0.0641(8) 1.000 . Uani d ? C(11) -0.0219(3) -0.149(1) -0.3311(3) 0.078(1) 1.000 . Uani d ? C(12) 0.0042(4) -0.315(1) -0.2823(3) 0.088(1) 1.000 . Uani d ? C(13) -0.0336(4) -0.359(1) -0.1726(3) 0.086(1) 1.000 . Uani d ? C(14) -0.0960(4) -0.241(1) -0.1133(3) 0.082(1) 1.000 . Uani d ? C(15) -0.1228(3) -0.077(1) -0.1627(2) 0.0684(8) 1.000 . Uani d ? C(16) -0.2729(3) 0.152(1) -0.4599(3) 0.087(1) 1.000 . Uani d ? C(17) -0.3248(4) 0.328(1) -0.5179(3) 0.099(1) 1.000 . Uani d ? C(18) -0.4637(4) 0.318(1) -0.6496(3) 0.137(2) 1.000 . Uani d ? H(4) 0.7649 0.3591 -0.0902 0.136 1.000 . Uiso c ? H(5) 0.6963 0.4511 0.0945 0.122 1.000 . Uiso c ? H(6) 0.2513 0.2328 -0.3785 0.091 1.000 . Uiso c ? H(9) -0.1332 0.2216 -0.2669 0.086 1.000 . Uiso c ? H(11) 0.0043 -0.1203 -0.4064 0.093 1.000 . Uiso c ? H(12) 0.0479 -0.3999 -0.3239 0.106 1.000 . Uiso c ? H(13) -0.0163 -0.4749 -0.1385 0.103 1.000 . Uiso c ? H(14) -0.1208 -0.2736 -0.0371 0.098 1.000 . Uiso c ? H(15) -0.1675 0.0020 -0.1212 0.082 1.000 . Uiso c ? H(16b) -0.2551 0.0827 -0.5273 0.104 1.000 . Uiso c ? H(16a) -0.3563 0.1007 -0.4386 0.104 1.000 . Uiso c ? H(17a) -0.2391 0.3798 -0.5323 0.118 1.000 . Uiso c ? H(17b) -0.3538 0.3900 -0.4553 0.118 1.000 . Uiso c ? H(18b) -0.5492 0.2592 -0.6360 0.164 1.000 . Uiso c ? H(18c) -0.4345 0.2535 -0.7133 0.164 1.000 . Uiso c ? H(18a) -0.4954 0.4274 -0.6827 0.164 1.000 . Uiso c ? loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 S(1) 0.1147(6) 0.1156(8) 0.1061(6) -0.0141(7) 0.0557(6) -0.0338(7) O(8) 0.096(1) 0.072(2) 0.070(1) -0.006(1) 0.0381(9) 0.014(1) N(3) 0.097(2) 0.102(2) 0.113(2) -0.014(2) 0.057(1) -0.021(2) N(7) 0.095(1) 0.054(2) 0.073(1) -0.008(1) 0.036(1) 0.003(1) C(2) 0.094(2) 0.053(2) 0.096(2) 0.003(2) 0.052(1) 0.010(1) C(4) 0.098(2) 0.111(3) 0.137(3) -0.014(2) 0.050(2) -0.044(2) C(5) 0.106(1) 0.081(2) 0.101(2) -0.015(3) 0.020(2) -0.015(2) C(6) 0.099(2) 0.056(2) 0.086(2) -0.001(2) 0.051(1) 0.012(2) C(9) 0.097(2) 0.057(2) 0.078(2) -0.001(2) 0.051(1) -0.001(1) C(10) 0.078(2) 0.056(1) 0.060(2) -0.007(1) 0.029(1) -0.003(1) C(11) 0.114(2) 0.062(2) 0.075(2) 0.008(2) 0.056(2) -0.006(1) C(12) 0.124(3) 0.061(2) 0.088(2) 0.008(2) 0.050(2) -0.005(2) C(13) 0.116(3) 0.057(2) 0.083(2) -0.001(2) 0.033(2) 0.007(2) C(14) 0.116(2) 0.069(2) 0.070(2) -0.009(2) 0.047(2) 0.006(1) C(15) 0.092(2) 0.062(2) 0.061(2) -0.005(2) 0.039(1) -0.007(1) C(16) 0.103(2) 0.078(2) 0.085(2) 0.006(2) 0.039(1) 0.016(2) C(17) 0.112(2) 0.082(2) 0.110(2) 0.024(2) 0.050(2) 0.022(2) C(18) 0.129(3) 0.146(4) 0.118(3) 0.036(3) 0.028(2) 0.021(3) #------------------------------------------------------------------------------ _refine_special_details ; ? ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme 'w = 1/[\s^2^(Fo) + 0.00000|Fo|^2^]' _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method 'Zachariasen (1967)' _refine_ls_extinction_coef 0.000069(2) _refine_ls_extinction_expression 'equ(3) Acta Cryst.(1968) A24, p213.' _refine_ls_abs_structure_details relative _refine_ls_abs_structure_Flack 0.055(69) _refine_ls_number_reflns 839 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.0386 _refine_ls_R_factor_gt 0.0386 _refine_ls_wR_factor_all 0.0254 _refine_ls_wR_factor_ref 0.0254 _refine_ls_goodness_of_fit_all 2.836 _refine_ls_goodness_of_fit_ref 2.836 _refine_ls_shift/esd_max 0.0470 _refine_ls_shift/esd_mean 0.0000 _refine_diff_density_min -0.13 _refine_diff_density_max 0.14 #------------------------------------------------------------------------------ _geom_special_details ; - ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag S(1) C(2) 1.711(5) . . yes S(1) C(5) 1.713(5) . . yes O(8) N(7) 1.378(4) . . yes O(8) C(9) 1.434(5) . . yes N(3) C(2) 1.289(4) . . yes N(3) C(4) 1.335(5) . . yes N(7) C(6) 1.266(4) . . yes C(2) C(6) 1.452(6) . . yes C(4) C(5) 1.337(6) . . yes C(4) H(4) 0.95 . . no C(5) H(5) 0.94 . . no C(6) H(6) 0.95 . . no C(9) C(10) 1.526(6) . . yes C(9) C(16) 1.530(6) . . yes C(9) H(9) 0.94 . . no C(10) C(11) 1.374(5) . . yes C(10) C(15) 1.369(5) . . yes C(11) C(12) 1.387(6) . . yes C(11) H(11) 0.95 . . no C(12) C(13) 1.380(6) . . yes C(12) H(12) 0.96 . . no C(13) C(14) 1.360(6) . . yes C(13) H(13) 0.97 . . no C(14) C(15) 1.373(7) . . yes C(14) H(14) 0.96 . . no C(15) H(15) 0.94 . . no C(16) C(17) 1.511(7) . . yes C(16) H(16b) 0.96 . . no C(16) H(16a) 0.96 . . no C(17) C(18) 1.498(6) . . yes C(17) H(17a) 0.94 . . no C(17) H(17b) 0.94 . . no C(18) H(18b) 0.96 . . no C(18) H(18c) 0.96 . . no C(18) H(18a) 0.93 . . no #------------------------------------------------------------------------------ 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C(2) S(1) C(5) 89.2(3) . . . yes N(7) O(8) C(9) 109.9(3) . . . yes C(2) N(3) C(4) 110.1(4) . . . yes O(8) N(7) C(6) 111.6(4) . . . yes S(1) C(2) N(3) 114.7(4) . . . yes S(1) C(2) C(6) 122.4(3) . . . yes N(3) C(2) C(6) 122.9(5) . . . yes N(3) C(4) C(5) 117.9(5) . . . yes N(3) C(4) H(4) 120.5 . . . no C(5) C(4) H(4) 121.6 . . . no S(1) C(5) C(4) 108.2(4) . . . yes S(1) C(5) H(5) 126.2 . . . no C(4) C(5) H(5) 125.6 . . . no N(7) C(6) C(2) 120.5(4) . . . yes N(7) C(6) H(6) 119.5 . . . no C(2) C(6) H(6) 120.0 . . . no O(8) C(9) C(10) 111.5(4) . . . yes O(8) C(9) C(16) 105.7(3) . . . yes O(8) C(9) H(9) 109.8 . . . no C(10) C(9) C(16) 112.0(4) . . . yes C(10) C(9) H(9) 108.3 . . . no C(16) C(9) H(9) 109.5 . . . no C(9) C(10) C(11) 119.0(4) . . . yes C(9) C(10) C(15) 121.5(4) . . . yes C(11) C(10) C(15) 119.4(4) . . . yes C(10) C(11) C(12) 120.3(4) . . . yes C(10) C(11) H(11) 120.9 . . . no C(12) C(11) H(11) 118.8 . . . no C(11) C(12) C(13) 119.4(5) . . . yes C(11) C(12) H(12) 121.2 . . . no C(13) C(12) H(12) 119.5 . . . no C(12) C(13) C(14) 120.1(5) . . . yes C(12) C(13) H(13) 119.7 . . . no C(14) C(13) H(13) 120.3 . . . no C(13) C(14) C(15) 120.4(4) . . . yes C(13) C(14) H(14) 118.7 . . . no C(15) C(14) H(14) 120.9 . . . no C(10) C(15) C(14) 120.6(4) . . . yes C(10) C(15) H(15) 120.6 . . . no C(14) C(15) H(15) 118.9 . . . no C(9) C(16) C(17) 114.9(4) . . . yes C(9) C(16) H(16b) 107.8 . . . no C(9) C(16) H(16a) 107.9 . . . no C(17) C(16) H(16b) 109.0 . . . no C(17) C(16) H(16a) 109.1 . . . no H(16b) C(16) H(16a) 107.8 . . . no C(16) C(17) C(18) 111.1(5) . . . yes C(16) C(17) H(17a) 108.1 . . . no C(16) C(17) H(17b) 108.1 . . . no C(18) C(17) H(17a) 109.2 . . . no C(18) C(17) H(17b) 109.2 . . . no H(17a) C(17) H(17b) 111.1 . . . no C(17) C(18) H(18b) 109.3 . . . no C(17) C(18) H(18c) 109.3 . . . no C(17) C(18) H(18a) 109.9 . . . no H(18b) C(18) H(18c) 107.9 . . . no H(18b) C(18) H(18a) 110.3 . . . no H(18c) C(18) H(18a) 110.2 . . . no #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O(8) C(11) 3.407(5) . 2_554 no #------------------------------------------------------------------------------