Electronic Supplementary Material for CrystEngComm This Journal is © The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Kraig Wheeler' 'Endia Casey' 'Beverly Harrington' 'Matt Zapp' _publ_contact_author_name 'Professor Kraig Wheeler' _publ_contact_author_address ; Department of Chemistry Delaware State University 1200 N. Dupont Hwy Dover Delaware 19901 UNITED STATES OF AMERICA ; _publ_contact_author_email kwheeler@dsc.edu _publ_contact_author_fax 302-857-6539 _publ_contact_author_phone 302-857-6537 _publ_requested_journal 'Cryst Eng. Comm.' _publ_section_title ; Competitive N-HO=C and N-HS=C hydrogen bonding in alanine dithiocarbamates ; data_compound1 _database_code_CSD 215740 _audit_creation_method SHELXL-97 _chemical_name_systematic ; N-[(Methylthio)thioxomethyl] Alanine ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C5 H9 N O2 S2' _chemical_formula_sum 'C5 H9 N O2 S2' _chemical_formula_weight 179.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.8327(5) _cell_length_b 7.6628(5) _cell_length_c 14.1769(7) _cell_angle_alpha 90.00 _cell_angle_beta 138.210(3) _cell_angle_gamma 90.00 _cell_volume 856.62(8) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 30 _cell_measurement_theta_min 23.431 _cell_measurement_theta_max 24.909 _exptl_crystal_description 'Transparent Plate' _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.62 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.390 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 0.566 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 'Siemens P4' _diffrn_measurement_method '\q/2\q\ scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% <3 _diffrn_reflns_number 3309 _diffrn_reflns_av_R_equivalents 0.0177 _diffrn_reflns_av_sigmaI/netI 0.0363 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 30.00 _reflns_number_total 2502 _reflns_number_gt 1558 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'XSCANS (Bruker, 1999)' _computing_cell_refinement 'XSCANS (Bruker, 1999)' _computing_data_reduction 'XSCANS (Bruker, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-SEED (Barbour, 2001)' _computing_publication_material 'X-SEED (Barbour, 2001)' _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^)+(0.0442P)^2^+0.4031P] 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 2502 _refine_ls_number_parameters 93 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0911 _refine_ls_R_factor_gt 0.0497 _refine_ls_wR_factor_ref 0.1324 _refine_ls_wR_factor_gt 0.1134 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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 0.68517(10) 0.19310(11) 0.50389(9) 0.0672(2) Uani 1 1 d . . . S2 S 0.67039(11) -0.17825(11) 0.42385(9) 0.0722(3) Uani 1 1 d . . . O1 O 1.0661(3) 0.4526(2) 0.66173(19) 0.0629(5) Uani 1 1 d . . . HO1 H 1.0461 0.5314 0.6118 0.076 Uiso 1 1 calc R . . O2 O 0.9700(2) 0.28646(19) 0.48446(17) 0.0430(4) Uani 1 1 d . . . N1 N 0.9394(2) 0.0096(2) 0.5935(2) 0.0418(4) Uani 1 1 d . . . HN1 H 0.9769 -0.0838 0.5905 0.050 Uiso 1 1 calc R . . C1 C 1.0227(3) 0.3028(3) 0.5974(2) 0.0399(5) Uani 1 1 d . . . C2 C 1.0562(3) 0.1511(3) 0.6842(2) 0.0408(5) Uani 1 1 d . . . H2 H 1.0422 0.1906 0.7407 0.049 Uiso 1 1 calc R . . C3 C 1.2379(3) 0.0888(4) 0.7833(3) 0.0588(7) Uani 1 1 d . . . H3A H 1.2625 -0.0023 0.8431 0.088 Uiso 1 1 calc R . . H3B H 1.3144 0.1845 0.8407 0.088 Uiso 1 1 calc R . . H3C H 1.2512 0.0447 0.7287 0.088 Uiso 1 1 calc R . . C4 C 0.7748(3) 0.0185(3) 0.5140(2) 0.0428(5) Uani 1 1 d . . . C5 C 0.4547(4) -0.1320(6) 0.3203(4) 0.0984(13) Uani 1 1 d . . . H5A H 0.4489 -0.0968 0.3816 0.148 Uiso 1 1 calc R . . H5B H 0.3870 -0.2348 0.2691 0.148 Uiso 1 1 calc R . . H5C H 0.4125 -0.0398 0.2547 0.148 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 0.0644(4) 0.0696(5) 0.0788(5) 0.0053(4) 0.0567(4) 0.0155(4) S2 0.0735(5) 0.0707(5) 0.0842(6) -0.0296(4) 0.0624(5) -0.0340(4) O1 0.1035(15) 0.0311(8) 0.0601(11) -0.0100(8) 0.0628(12) -0.0126(9) O2 0.0597(10) 0.0293(8) 0.0459(9) -0.0010(6) 0.0411(8) 0.0002(7) N1 0.0492(10) 0.0288(9) 0.0552(11) -0.0016(8) 0.0412(10) -0.0014(8) C1 0.0464(12) 0.0288(10) 0.0465(12) -0.0024(9) 0.0352(11) -0.0004(9) C2 0.0476(12) 0.0327(11) 0.0444(12) -0.0012(9) 0.0350(11) -0.0031(9) C3 0.0501(14) 0.0548(16) 0.0554(15) 0.0120(13) 0.0345(13) 0.0021(12) C4 0.0513(13) 0.0450(13) 0.0438(12) 0.0001(10) 0.0389(11) -0.0039(10) C5 0.0634(19) 0.154(4) 0.080(2) -0.033(3) 0.0539(19) -0.044(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 S1 C4 1.646(2) . ? S2 C4 1.754(2) . ? S2 C5 1.791(4) . ? O1 C1 1.309(3) . ? O1 HO1 0.8200 . ? O2 C1 1.216(3) . ? N1 C4 1.340(3) . ? N1 C2 1.446(3) . ? N1 HN1 0.8600 . ? C1 C2 1.515(3) . ? C2 C3 1.522(3) . ? C2 H2 0.9800 . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? 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 C4 S2 C5 103.06(17) . . ? C1 O1 HO1 109.5 . . ? C4 N1 C2 122.47(19) . . ? C4 N1 HN1 118.8 . . ? C2 N1 HN1 118.8 . . ? O2 C1 O1 123.9(2) . . ? O2 C1 C2 123.85(19) . . ? O1 C1 C2 112.17(19) . . ? N1 C2 C1 110.82(18) . . ? N1 C2 C3 109.97(19) . . ? C1 C2 C3 108.99(18) . . ? N1 C2 H2 109.0 . . ? C1 C2 H2 109.0 . . ? C3 C2 H2 109.0 . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N1 C4 S1 123.53(18) . . ? N1 C4 S2 111.19(17) . . ? S1 C4 S2 125.28(14) . . ? S2 C5 H5A 109.5 . . ? S2 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? S2 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? 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 N1 C2 C1 -71.6(3) . . . . ? C4 N1 C2 C3 167.9(2) . . . . ? O2 C1 C2 N1 -32.1(3) . . . . ? O1 C1 C2 N1 151.6(2) . . . . ? O2 C1 C2 C3 89.0(3) . . . . ? O1 C1 C2 C3 -87.3(2) . . . . ? C2 N1 C4 S1 3.3(3) . . . . ? C2 N1 C4 S2 -176.83(16) . . . . ? C5 S2 C4 N1 -177.36(18) . . . . ? C5 S2 C4 S1 2.5(2) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.363 _refine_diff_density_min -0.347 _refine_diff_density_rms 0.050 #==END data_compound2 _database_code_CSD 215741 _audit_creation_method SHELXL-97 _chemical_name_systematic ; N-[(Ethylthio)thioxomethyl] Alanine ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H11 N O2 S2' _chemical_formula_sum 'C6 H11 N O2 S2' _chemical_formula_weight 193.28 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.8922(14) _cell_length_b 7.4758(16) _cell_length_c 14.305(2) _cell_angle_alpha 90.00 _cell_angle_beta 99.742(11) _cell_angle_gamma 90.00 _cell_volume 937.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 26 _cell_measurement_theta_min 21.470 _cell_measurement_theta_max 24.941 _exptl_crystal_description 'Transparent Plate' _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.62 _exptl_crystal_size_mid 0.58 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.370 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.523 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 'Siemens P4' _diffrn_measurement_method '\q/2\q\ scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% <3 _diffrn_reflns_number 2149 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0549 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2149 _reflns_number_gt 1247 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'XSCANS (Bruker, 1999)' _computing_cell_refinement 'XSCANS (Bruker, 1999)' _computing_data_reduction 'XSCANS (Bruker, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-SEED (Barbour, 2001)' _computing_publication_material 'X-SEED (Barbour, 2001)' _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^)+(0.0429P)^2^+0.2602P] 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 2149 _refine_ls_number_parameters 102 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1013 _refine_ls_R_factor_gt 0.0505 _refine_ls_wR_factor_ref 0.1210 _refine_ls_wR_factor_gt 0.1027 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.007 _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 0.69371(11) 0.16560(13) 0.66524(7) 0.0798(3) Uani 1 1 d . . . S2 S 0.70145(9) -0.20757(11) 0.58879(6) 0.0655(3) Uani 1 1 d . . . N1 N 0.9315(3) 0.0005(3) 0.62190(14) 0.0480(6) Uani 1 1 d . . . HN1 H 0.9699 -0.0912 0.5983 0.058 Uiso 1 1 calc R . . O1 O 1.0417(3) 0.4548(3) 0.62675(13) 0.0646(6) Uani 1 1 d . . . HO1 H 1.0256 0.5351 0.5873 0.077 Uiso 1 1 calc R . . O2 O 0.9659(2) 0.2847(2) 0.50071(12) 0.0484(5) Uani 1 1 d . . . C1 C 1.0055(3) 0.3019(3) 0.58581(19) 0.0438(6) Uani 1 1 d . . . C2 C 1.0310(3) 0.1485(4) 0.65347(18) 0.0481(7) Uani 1 1 d . . . H2 H 1.0110 0.1885 0.7154 0.058 Uiso 1 1 calc R . . C3 C 1.1961(3) 0.0887(4) 0.6639(2) 0.0644(9) Uani 1 1 d . . . H3A H 1.2151 -0.0036 0.7112 0.097 Uiso 1 1 calc R . . H3B H 1.2621 0.1885 0.6829 0.097 Uiso 1 1 calc R . . H3C H 1.2155 0.0431 0.6044 0.097 Uiso 1 1 calc R . . C4 C 0.7837(3) -0.0025(4) 0.62720(17) 0.0500(7) Uani 1 1 d . . . C5 C 0.5107(4) -0.1903(6) 0.6133(3) 0.0841(11) Uani 1 1 d . . . H5A H 0.5137 -0.1517 0.6783 0.101 Uiso 1 1 calc R . . H5B H 0.4546 -0.1016 0.5718 0.101 Uiso 1 1 calc R . . C6 C 0.4331(4) -0.3629(6) 0.5987(3) 0.1017(14) Uani 1 1 d . . . H6A H 0.4187 -0.3938 0.5326 0.153 Uiso 1 1 calc R . . H6B H 0.3357 -0.3554 0.6189 0.153 Uiso 1 1 calc R . . H6C H 0.4940 -0.4531 0.6350 0.153 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 0.0797(6) 0.0708(6) 0.0932(7) -0.0143(5) 0.0273(5) 0.0204(5) S2 0.0595(5) 0.0563(5) 0.0858(6) -0.0043(4) 0.0270(4) -0.0050(4) N1 0.0573(15) 0.0369(12) 0.0536(13) -0.0009(11) 0.0202(11) 0.0022(11) O1 0.1031(18) 0.0392(11) 0.0473(11) -0.0042(9) 0.0008(11) -0.0093(11) O2 0.0653(13) 0.0385(10) 0.0408(10) -0.0040(9) 0.0071(9) 0.0012(9) C1 0.0476(15) 0.0367(14) 0.0477(16) -0.0042(13) 0.0100(12) 0.0023(13) C2 0.0622(18) 0.0429(15) 0.0398(14) -0.0026(12) 0.0103(13) -0.0011(14) C3 0.0573(19) 0.066(2) 0.0658(19) 0.0127(17) -0.0013(15) 0.0021(17) C4 0.0602(19) 0.0476(16) 0.0442(15) 0.0076(13) 0.0147(14) 0.0083(14) C5 0.055(2) 0.095(3) 0.107(3) 0.004(2) 0.0269(19) 0.000(2) C6 0.070(3) 0.125(4) 0.117(3) -0.002(3) 0.035(2) -0.021(3) _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 C4 1.632(3) . ? S2 C4 1.747(3) . ? S2 C5 1.794(3) . ? N1 C4 1.329(3) . ? N1 C2 1.441(3) . ? N1 HN1 0.8600 . ? O1 C1 1.300(3) . ? O1 HO1 0.8200 . ? O2 C1 1.216(3) . ? C1 C2 1.493(4) . ? C2 C3 1.518(4) . ? C2 H2 0.9800 . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C5 C6 1.461(6) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? 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 C4 S2 C5 103.59(17) . . ? C4 N1 C2 123.7(2) . . ? C4 N1 HN1 118.1 . . ? C2 N1 HN1 118.1 . . ? C1 O1 HO1 109.5 . . ? O2 C1 O1 123.5(2) . . ? O2 C1 C2 123.7(2) . . ? O1 C1 C2 112.6(2) . . ? N1 C2 C1 111.7(2) . . ? N1 C2 C3 109.7(2) . . ? C1 C2 C3 109.2(2) . . ? N1 C2 H2 108.8 . . ? C1 C2 H2 108.8 . . ? C3 C2 H2 108.8 . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N1 C4 S1 123.5(2) . . ? N1 C4 S2 111.2(2) . . ? S1 C4 S2 125.32(18) . . ? C6 C5 S2 110.4(3) . . ? C6 C5 H5A 109.6 . . ? S2 C5 H5A 109.6 . . ? C6 C5 H5B 109.6 . . ? S2 C5 H5B 109.6 . . ? H5A C5 H5B 108.1 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? 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 N1 C2 C1 -75.1(3) . . . . ? C4 N1 C2 C3 163.7(2) . . . . ? O2 C1 C2 N1 -31.7(4) . . . . ? O1 C1 C2 N1 153.3(2) . . . . ? O2 C1 C2 C3 89.7(3) . . . . ? O1 C1 C2 C3 -85.2(3) . . . . ? C2 N1 C4 S1 3.2(4) . . . . ? C2 N1 C4 S2 -176.61(19) . . . . ? C5 S2 C4 N1 174.3(2) . . . . ? C5 S2 C4 S1 -5.6(2) . . . . ? C4 S2 C5 C6 -171.2(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.204 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.045 #==END data_compound3 _database_code_CSD 215742 _audit_creation_method SHELXL-97 _chemical_name_systematic ; N-[(Isopropylthio)thioxomethyl] Alanine ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H13 N O2 S2' _chemical_formula_sum 'C7 H13 N O2 S2' _chemical_formula_weight 207.30 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.198(4) _cell_length_b 7.613(2) _cell_length_c 11.927(4) _cell_angle_alpha 90.00 _cell_angle_beta 116.710(10) _cell_angle_gamma 90.00 _cell_volume 1070.5(6) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 22 _cell_measurement_theta_min 16.571 _cell_measurement_theta_max 21.034 _exptl_crystal_description 'Transparent Waxy Needle' _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.72 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.286 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 0.462 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; Recrystallization experiments produced less than desirable crystalline samples. Crystals extinguished plane polarized light, but faces and edges appeared less than ideal. Crystallographic investigations indicated these samples to be poor diffractors. Data collection stopped at final stages of process due to lack of reflection occurence. ; _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 'Siemens P4' _diffrn_measurement_method '\q/2\q\ scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% <3 _diffrn_reflns_number 2989 _diffrn_reflns_av_R_equivalents 0.0799 _diffrn_reflns_av_sigmaI/netI 0.0927 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.19 _diffrn_reflns_theta_max 27.51 _reflns_number_total 2284 _reflns_number_gt 1066 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'XSCANS (Bruker, 1999)' _computing_cell_refinement 'XSCANS (Bruker, 1999)' _computing_data_reduction 'XSCANS (Bruker, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-SEED (Barbour, 2001)' _computing_publication_material 'X-SEED (Barbour, 2001)' _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^)+(0.0985P)^2^+0.1179P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.005(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2284 _refine_ls_number_parameters 114 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1638 _refine_ls_R_factor_gt 0.0744 _refine_ls_wR_factor_ref 0.2184 _refine_ls_wR_factor_gt 0.1749 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _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 0.68732(13) 0.8116(2) 0.42361(18) 0.0843(6) Uani 1 1 d . . . S2 S 0.76011(11) 1.18372(19) 0.50678(16) 0.0752(6) Uani 1 1 d . . . O1 O 0.8919(3) 0.5498(4) 0.3449(3) 0.0727(11) Uani 1 1 d . . . HO1 H 0.9269 0.4701 0.3929 0.087 Uiso 1 1 calc R . . O2 O 0.9877(3) 0.7130(4) 0.5129(4) 0.0552(9) Uani 1 1 d . . . N1 N 0.8416(3) 0.9897(5) 0.3935(4) 0.0523(10) Uani 1 1 d . . . HN1 H 0.8851 1.0800 0.4102 0.063 Uiso 1 1 calc R . . C1 C 0.9176(4) 0.6977(6) 0.4046(5) 0.0505(11) Uani 1 1 d . . . C2 C 0.8564(4) 0.8491(6) 0.3218(5) 0.0542(12) Uani 1 1 d . . . H2 H 0.7817 0.8093 0.2591 0.065 Uiso 1 1 calc R . . C3 C 0.9227(5) 0.9128(8) 0.2558(5) 0.0729(16) Uani 1 1 d . . . H3A H 0.8823 1.0067 0.1998 0.109 Uiso 1 1 calc R . . H3B H 0.9330 0.8181 0.2087 0.109 Uiso 1 1 calc R . . H3C H 0.9954 0.9545 0.3165 0.109 Uiso 1 1 calc R . . C4 C 0.7637(3) 0.9858(6) 0.4349(4) 0.0532(13) Uani 1 1 d . . . C5 C 0.6301(4) 1.1724(8) 0.5221(5) 0.0713(16) Uani 1 1 d . . . H5 H 0.6160 1.0489 0.5336 0.086 Uiso 1 1 calc R . . C6 C 0.5343(6) 1.2353(14) 0.4040(9) 0.158(4) Uani 1 1 d . . . H6A H 0.4640 1.2156 0.4076 0.238 Uiso 1 1 calc R . . H6B H 0.5339 1.1724 0.3340 0.238 Uiso 1 1 calc R . . H6C H 0.5432 1.3586 0.3940 0.238 Uiso 1 1 calc R . . C7 C 0.6449(7) 1.2679(15) 0.6338(8) 0.177(5) Uani 1 1 d . . . H7A H 0.6758 1.3820 0.6335 0.266 Uiso 1 1 calc R . . H7B H 0.6960 1.2044 0.7070 0.266 Uiso 1 1 calc R . . H7C H 0.5729 1.2804 0.6346 0.266 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 0.0776(10) 0.0727(10) 0.1224(15) -0.0241(9) 0.0625(10) -0.0235(8) S2 0.0601(8) 0.0684(9) 0.1075(13) -0.0318(9) 0.0467(8) -0.0071(7) O1 0.100(3) 0.045(2) 0.067(2) -0.0082(19) 0.031(2) 0.0082(19) O2 0.0632(19) 0.0421(18) 0.063(2) -0.0004(17) 0.0303(18) -0.0009(16) N1 0.055(2) 0.042(2) 0.069(3) -0.003(2) 0.035(2) -0.0008(18) C1 0.056(3) 0.048(3) 0.056(3) -0.006(3) 0.032(3) -0.001(2) C2 0.059(3) 0.049(3) 0.062(3) -0.002(2) 0.032(3) 0.006(2) C3 0.085(3) 0.072(4) 0.081(4) 0.019(3) 0.053(3) 0.024(3) C4 0.044(2) 0.056(3) 0.061(3) -0.005(2) 0.025(2) 0.002(2) C5 0.053(3) 0.086(4) 0.081(4) -0.020(3) 0.035(3) -0.002(3) C6 0.076(5) 0.252(12) 0.144(7) 0.044(8) 0.047(5) 0.059(6) C7 0.096(5) 0.330(16) 0.124(7) -0.104(9) 0.066(5) -0.027(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 C4 1.634(5) . ? S2 C4 1.745(5) . ? S2 C5 1.808(5) . ? O1 C1 1.294(5) . ? O1 HO1 0.8200 . ? O2 C1 1.210(6) . ? N1 C4 1.327(6) . ? N1 C2 1.437(6) . ? N1 HN1 0.8600 . ? C1 C2 1.496(7) . ? C2 C3 1.497(6) . ? C2 H2 0.9800 . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C5 C7 1.451(9) . ? C5 C6 1.487(9) . ? C5 H5 0.9800 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? 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 C4 S2 C5 104.2(2) . . ? C1 O1 HO1 109.5 . . ? C4 N1 C2 122.7(4) . . ? C4 N1 HN1 118.6 . . ? C2 N1 HN1 118.6 . . ? O2 C1 O1 123.9(5) . . ? O2 C1 C2 123.9(5) . . ? O1 C1 C2 112.1(5) . . ? N1 C2 C1 111.0(4) . . ? N1 C2 C3 109.9(4) . . ? C1 C2 C3 109.1(4) . . ? N1 C2 H2 109.0 . . ? C1 C2 H2 109.0 . . ? C3 C2 H2 109.0 . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N1 C4 S1 122.7(4) . . ? N1 C4 S2 111.1(3) . . ? S1 C4 S2 126.1(3) . . ? C7 C5 C6 114.5(7) . . ? C7 C5 S2 109.0(4) . . ? C6 C5 S2 109.3(5) . . ? C7 C5 H5 108.0 . . ? C6 C5 H5 108.0 . . ? S2 C5 H5 108.0 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C5 C7 H7A 109.5 . . ? C5 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C5 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? 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 N1 C2 C1 -76.9(5) . . . . ? C4 N1 C2 C3 162.4(4) . . . . ? O2 C1 C2 N1 -31.2(6) . . . . ? O1 C1 C2 N1 152.8(4) . . . . ? O2 C1 C2 C3 90.0(6) . . . . ? O1 C1 C2 C3 -86.1(5) . . . . ? C2 N1 C4 S1 7.7(6) . . . . ? C2 N1 C4 S2 -175.0(3) . . . . ? C5 S2 C4 N1 166.9(3) . . . . ? C5 S2 C4 S1 -15.9(4) . . . . ? C4 S2 C5 C7 148.5(6) . . . . ? C4 S2 C5 C6 -85.7(6) . . . . ? _diffrn_measured_fraction_theta_max 0.925 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.925 _refine_diff_density_max 0.415 _refine_diff_density_min -0.251 _refine_diff_density_rms 0.064 #==END data_compound4 _database_code_CSD 215743 _audit_creation_method SHELXL-97 _chemical_name_systematic ; N-[(Benzylthio)thioxomethyl] Alanine ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H13 N O2 S2' _chemical_formula_sum 'C11 H13 N O2 S2' _chemical_formula_weight 255.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.046(2) _cell_length_b 10.840(1) _cell_length_c 8.852(1) _cell_angle_alpha 90.00 _cell_angle_beta 107.97(1) _cell_angle_gamma 90.00 _cell_volume 1282.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 35 _cell_measurement_theta_min 23.246 _cell_measurement_theta_max 24.856 _exptl_crystal_description 'Transparent Block' _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.52 _exptl_crystal_size_min 0.48 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.323 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.400 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 'Siemens P4' _diffrn_measurement_method '\q/2\q\ scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% <3 _diffrn_reflns_number 3572 _diffrn_reflns_av_R_equivalents 0.0165 _diffrn_reflns_av_sigmaI/netI 0.0368 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 1 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 27.51 _reflns_number_total 2942 _reflns_number_gt 2081 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'XSCANS (Bruker, 1999)' _computing_cell_refinement 'XSCANS (Bruker, 1999)' _computing_data_reduction 'XSCANS (Bruker, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-SEED (Barbour, 2001)' _computing_publication_material 'X-SEED (Barbour, 2001)' _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^)+(0.0571P)^2^+0.4445P] 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 2942 _refine_ls_number_parameters 146 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0716 _refine_ls_R_factor_gt 0.0429 _refine_ls_wR_factor_ref 0.1124 _refine_ls_wR_factor_gt 0.0994 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _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 0.78848(4) 0.42960(6) -0.05641(7) 0.05359(18) Uani 1 1 d . . . S2 S 0.91589(4) 0.29602(6) 0.23573(7) 0.05434(19) Uani 1 1 d . . . O1 O 0.51051(11) 0.39155(16) -0.14119(17) 0.0592(5) Uani 1 1 d . . . HO1 H 0.4834 0.4553 -0.1260 0.071 Uiso 1 1 calc R . . O2 O 0.59249(11) 0.41228(15) 0.11712(17) 0.0534(4) Uani 1 1 d . . . N1 N 0.73279(12) 0.24246(17) 0.0882(2) 0.0423(4) Uani 1 1 d . . . HN1 H 0.7463 0.1893 0.1640 0.051 Uiso 1 1 calc R . . C1 C 0.57743(14) 0.3594(2) -0.0123(2) 0.0428(5) Uani 1 1 d . . . C2 C 0.63302(14) 0.2428(2) -0.0261(2) 0.0415(5) Uani 1 1 d . . . H2 H 0.6390 0.2382 -0.1334 0.050 Uiso 1 1 calc R . . C3 C 0.57337(16) 0.1321(2) -0.0003(3) 0.0556(6) Uani 1 1 d . . . H3A H 0.6076 0.0575 -0.0111 0.083 Uiso 1 1 calc R . . H3B H 0.5082 0.1330 -0.0778 0.083 Uiso 1 1 calc R . . H3C H 0.5667 0.1359 0.1043 0.083 Uiso 1 1 calc R . . C4 C 0.80443(14) 0.32106(19) 0.0807(2) 0.0409(5) Uani 1 1 d . . . C5 C 1.00063(17) 0.4097(2) 0.1994(3) 0.0624(7) Uani 1 1 d . . . H5A H 1.0080 0.3980 0.0949 0.075 Uiso 1 1 calc R . . H5B H 0.9754 0.4924 0.2052 0.075 Uiso 1 1 calc R . . C6 C 1.09953(16) 0.3916(2) 0.3262(3) 0.0532(6) Uani 1 1 d . . . C7 C 1.1607(2) 0.2964(3) 0.3139(4) 0.0771(9) Uani 1 1 d . . . H7 H 1.1413 0.2440 0.2265 0.093 Uiso 1 1 calc R . . C8 C 1.2511(2) 0.2774(3) 0.4304(4) 0.0894(10) Uani 1 1 d . . . H8 H 1.2924 0.2125 0.4215 0.107 Uiso 1 1 calc R . . C9 C 1.27976(19) 0.3547(3) 0.5591(4) 0.0770(9) Uani 1 1 d . . . H9 H 1.3405 0.3420 0.6378 0.092 Uiso 1 1 calc R . . C10 C 1.2196(2) 0.4497(3) 0.5720(3) 0.0722(8) Uani 1 1 d . . . H10 H 1.2395 0.5022 0.6592 0.087 Uiso 1 1 calc R . . C11 C 1.12915(18) 0.4686(2) 0.4560(3) 0.0604(6) Uani 1 1 d . . . H11 H 1.0881 0.5336 0.4656 0.073 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 0.0545(3) 0.0504(3) 0.0507(3) 0.0051(3) 0.0085(3) -0.0059(3) S2 0.0397(3) 0.0572(4) 0.0572(4) 0.0070(3) 0.0019(2) -0.0057(2) O1 0.0513(8) 0.0683(11) 0.0447(8) -0.0091(8) -0.0044(7) 0.0202(8) O2 0.0539(9) 0.0607(10) 0.0390(8) -0.0085(7) 0.0046(7) 0.0133(7) N1 0.0359(8) 0.0424(9) 0.0450(9) 0.0044(8) 0.0072(7) 0.0023(7) C1 0.0357(9) 0.0487(12) 0.0399(11) -0.0028(10) 0.0058(8) -0.0003(9) C2 0.0360(9) 0.0453(11) 0.0402(11) -0.0044(9) 0.0074(8) 0.0005(9) C3 0.0477(12) 0.0507(14) 0.0677(15) -0.0056(12) 0.0169(11) -0.0072(11) C4 0.0374(10) 0.0407(11) 0.0431(11) -0.0057(9) 0.0103(8) 0.0026(8) C5 0.0456(12) 0.0659(16) 0.0685(16) 0.0073(13) 0.0074(11) -0.0131(11) C6 0.0411(11) 0.0595(15) 0.0569(13) 0.0017(12) 0.0121(10) -0.0110(10) C7 0.0551(15) 0.090(2) 0.0787(19) -0.0277(16) 0.0094(13) 0.0029(14) C8 0.0521(15) 0.099(3) 0.109(3) -0.008(2) 0.0119(16) 0.0113(16) C9 0.0461(13) 0.101(2) 0.0717(18) 0.0117(18) -0.0005(12) -0.0139(15) C10 0.0678(17) 0.083(2) 0.0598(16) -0.0104(15) 0.0106(13) -0.0296(16) C11 0.0585(14) 0.0525(14) 0.0697(16) -0.0071(13) 0.0191(12) -0.0157(12) _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 C4 1.655(2) . ? S2 C4 1.756(2) . ? S2 C5 1.810(2) . ? O1 C1 1.283(2) . ? O1 HO1 0.8200 . ? O2 C1 1.240(2) . ? N1 C4 1.336(3) . ? N1 C2 1.454(2) . ? N1 HN1 0.8600 . ? C1 C2 1.510(3) . ? C2 C3 1.520(3) . ? C2 H2 0.9800 . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C5 C6 1.506(3) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.369(4) . ? C6 C11 1.377(3) . ? C7 C8 1.382(4) . ? C7 H7 0.9300 . ? C8 C9 1.370(4) . ? C8 H8 0.9300 . ? C9 C10 1.359(4) . ? C9 H9 0.9300 . ? C10 C11 1.380(3) . ? C10 H10 0.9300 . ? C11 H11 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 C4 S2 C5 103.44(11) . . ? C1 O1 HO1 109.5 . . ? C4 N1 C2 122.91(18) . . ? C4 N1 HN1 118.5 . . ? C2 N1 HN1 118.5 . . ? O2 C1 O1 124.4(2) . . ? O2 C1 C2 121.14(18) . . ? O1 C1 C2 114.26(18) . . ? N1 C2 C1 110.92(16) . . ? N1 C2 C3 110.56(18) . . ? C1 C2 C3 108.99(17) . . ? N1 C2 H2 108.8 . . ? C1 C2 H2 108.8 . . ? C3 C2 H2 108.8 . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N1 C4 S1 123.79(15) . . ? N1 C4 S2 111.49(15) . . ? S1 C4 S2 124.71(12) . . ? C6 C5 S2 106.53(17) . . ? C6 C5 H5A 110.4 . . ? S2 C5 H5A 110.4 . . ? C6 C5 H5B 110.4 . . ? S2 C5 H5B 110.4 . . ? H5A C5 H5B 108.6 . . ? C7 C6 C11 119.2(2) . . ? C7 C6 C5 119.8(2) . . ? C11 C6 C5 121.0(2) . . ? C6 C7 C8 120.5(3) . . ? C6 C7 H7 119.7 . . ? C8 C7 H7 119.7 . . ? C9 C8 C7 119.7(3) . . ? C9 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? C10 C9 C8 120.2(3) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C9 C10 C11 120.2(3) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? C6 C11 C10 120.2(3) . . ? C6 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? 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 N1 C2 C1 -66.9(2) . . . . ? C4 N1 C2 C3 172.06(19) . . . . ? O2 C1 C2 N1 -31.8(3) . . . . ? O1 C1 C2 N1 152.84(19) . . . . ? O2 C1 C2 C3 90.2(2) . . . . ? O1 C1 C2 C3 -85.2(2) . . . . ? C2 N1 C4 S1 1.1(3) . . . . ? C2 N1 C4 S2 -179.84(15) . . . . ? C5 S2 C4 N1 179.19(16) . . . . ? C5 S2 C4 S1 -1.80(18) . . . . ? C4 S2 C5 C6 -178.54(17) . . . . ? S2 C5 C6 C7 77.7(3) . . . . ? S2 C5 C6 C11 -101.5(2) . . . . ? C11 C6 C7 C8 0.1(4) . . . . ? C5 C6 C7 C8 -179.1(3) . . . . ? C6 C7 C8 C9 -0.1(5) . . . . ? C7 C8 C9 C10 -0.2(5) . . . . ? C8 C9 C10 C11 0.3(4) . . . . ? C7 C6 C11 C10 0.0(4) . . . . ? C5 C6 C11 C10 179.3(2) . . . . ? C9 C10 C11 C6 -0.3(4) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.218 _refine_diff_density_min -0.195 _refine_diff_density_rms 0.043 #==END