#------------------------------------------------------------------------------ #$Date: 2016-03-21 02:55:05 +0200 (Mon, 21 Mar 2016) $ #$Revision: 178411 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/02/32/4023263.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_4023263 loop_ _publ_author_name 'Ahmad Basheer' 'Zvi Rappoport' _publ_section_title ; A Rich Array of Reactions of Cyanomonothiocarbonylmalonamides RNHCSCH(CN)CONHR' and Their Thioenols RNHC(SH)=C(CN)CONHR' ; _journal_name_full 'Journal of Organic Chemistry' _journal_page_first 1386 _journal_page_last 1396 _journal_paper_doi 10.1021/jo7022262 _journal_volume 73 _journal_year 2008 _chemical_formula_moiety 'C10 H7 N3 S2' _chemical_formula_sum 'C10 H7 N3 S2' _chemical_formula_weight 233.31 _chemical_name_systematic ; ? ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 95.5850(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 4.3559(3) _cell_length_b 17.3837(10) _cell_length_c 13.9844(8) _cell_measurement_temperature 295(1) _cell_volume 1053.90(11) _computing_cell_refinement 'Bruker SMART' _computing_data_collection 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 295(1) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0201 _diffrn_reflns_av_sigmaI/netI 0.0155 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 11639 _diffrn_reflns_theta_full 27.00 _diffrn_reflns_theta_max 27.00 _diffrn_reflns_theta_min 1.87 _exptl_absorpt_coefficient_mu 0.471 _exptl_absorpt_correction_T_max 0.9199 _exptl_absorpt_correction_T_min 0.8561 _exptl_absorpt_correction_type none _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.470 _exptl_crystal_density_method 'not measured' _exptl_crystal_description rod _exptl_crystal_F_000 480 _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.18 _refine_diff_density_max 0.290 _refine_diff_density_min -0.245 _refine_diff_density_rms 0.065 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 164 _refine_ls_number_reflns 2302 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.037 _refine_ls_R_factor_all 0.0410 _refine_ls_R_factor_gt 0.0371 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0684P)^2^+0.1873P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1034 _refine_ls_wR_factor_ref 0.1064 _reflns_number_gt 2056 _reflns_number_total 2302 _reflns_threshold_expression >2sigma(I) _cod_data_source_file jo7022262-File006.cif _cod_data_source_block bashir3m _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius ; _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 4023263 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' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.3721(3) 0.69305(9) 0.89177(10) 0.0404(3) Uani 1 1 d . . . C2 C 0.5612(4) 0.62807(8) 0.88823(11) 0.0417(3) Uani 1 1 d . . . C3 C 0.6482(3) 0.59297(9) 0.80182(11) 0.0428(3) Uani 1 1 d . . . C4 C 0.6824(4) 0.59658(9) 0.97777(12) 0.0481(4) Uani 1 1 d . . . C5 C 0.0596(4) 0.79420(9) 0.83744(12) 0.0455(4) Uani 1 1 d . . . C6 C 0.0806(4) 0.80873(9) 0.93558(12) 0.0479(4) Uani 1 1 d . . . C7 C -0.0636(5) 0.87217(12) 0.97119(17) 0.0628(5) Uani 1 1 d . . . C8 C -0.2324(5) 0.91902(13) 0.90594(19) 0.0715(6) Uani 1 1 d . . . C9 C -0.2554(5) 0.90368(12) 0.80820(18) 0.0665(5) Uani 1 1 d . . . C10 C -0.1090(4) 0.84153(11) 0.77208(16) 0.0585(4) Uani 1 1 d . . . H7 H -0.056(6) 0.8805(14) 1.0374(19) 0.079(7) Uiso 1 1 d . . . H8 H -0.317(6) 0.9605(17) 0.9254(19) 0.090(8) Uiso 1 1 d . . . H9 H -0.375(5) 0.9344(13) 0.7646(16) 0.069(6) Uiso 1 1 d . . . H10 H -0.140(6) 0.8267(14) 0.7069(19) 0.078(7) Uiso 1 1 d . . . N1 N 0.2254(3) 0.72906(8) 0.81645(11) 0.0451(3) Uani 1 1 d . . . H1N1 H 0.243(4) 0.7146(11) 0.7607(15) 0.049(5) Uiso 1 1 d . . . N2 N 0.7822(5) 0.56997(10) 1.04870(12) 0.0692(5) Uani 1 1 d . . . N3 N 0.8398(4) 0.53324(9) 0.81136(13) 0.0548(4) Uani 1 1 d . . . H1N3 H 0.920(5) 0.5167(12) 0.8648(16) 0.061(6) Uiso 1 1 d . . . H2N3 H 0.895(5) 0.5134(13) 0.7605(18) 0.065(6) Uiso 1 1 d . . . S1 S 0.30509(11) 0.73858(3) 0.99863(3) 0.05119(16) Uani 1 1 d . . . S2 S 0.52662(12) 0.62257(3) 0.68935(3) 0.05812(17) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0418(7) 0.0426(7) 0.0361(7) 0.0014(6) 0.0009(6) -0.0078(6) C2 0.0453(8) 0.0426(8) 0.0358(7) 0.0037(6) -0.0037(6) -0.0040(6) C3 0.0421(7) 0.0455(8) 0.0400(7) 0.0022(6) -0.0003(6) -0.0041(6) C4 0.0573(9) 0.0440(8) 0.0415(8) -0.0001(6) -0.0031(7) -0.0008(7) C5 0.0423(8) 0.0433(8) 0.0515(9) 0.0051(7) 0.0070(7) -0.0032(6) C6 0.0470(8) 0.0457(8) 0.0521(9) 0.0021(7) 0.0106(7) -0.0055(6) C7 0.0660(12) 0.0563(10) 0.0694(13) -0.0044(9) 0.0233(10) -0.0018(8) C8 0.0636(12) 0.0517(11) 0.1035(18) 0.0000(11) 0.0295(12) 0.0068(9) C9 0.0549(10) 0.0547(10) 0.0907(16) 0.0204(10) 0.0102(10) 0.0051(8) C10 0.0561(10) 0.0564(10) 0.0626(12) 0.0130(9) 0.0036(8) 0.0032(8) N1 0.0510(7) 0.0464(7) 0.0374(7) 0.0021(5) 0.0017(6) 0.0019(6) N2 0.0934(13) 0.0649(10) 0.0453(8) 0.0043(7) -0.0129(8) 0.0099(9) N3 0.0593(9) 0.0571(9) 0.0466(9) -0.0007(7) -0.0024(7) 0.0120(7) S1 0.0629(3) 0.0523(3) 0.0382(2) -0.00165(15) 0.00435(18) -0.00186(18) S2 0.0682(3) 0.0709(3) 0.0347(2) 0.00269(18) 0.00206(19) 0.0163(2) 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' 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 N1 C1 C2 126.04(14) . . ? N1 C1 S1 110.92(12) . . ? C2 C1 S1 123.02(11) . . ? C1 C2 C4 116.67(14) . . ? C1 C2 C3 125.15(13) . . ? C4 C2 C3 118.15(14) . . ? N3 C3 C2 117.46(14) . . ? N3 C3 S2 117.87(13) . . ? C2 C3 S2 124.67(12) . . ? N2 C4 C2 178.5(2) . . ? C10 C5 C6 121.53(17) . . ? C10 C5 N1 126.68(17) . . ? C6 C5 N1 111.78(14) . . ? C7 C6 C5 120.74(18) . . ? C7 C6 S1 128.70(16) . . ? C5 C6 S1 110.56(12) . . ? C8 C7 C6 117.6(2) . . ? C8 C7 H7 122.0(15) . . ? C6 C7 H7 120.4(15) . . ? C7 C8 C9 121.4(2) . . ? C7 C8 H8 119.9(19) . . ? C9 C8 H8 118.5(19) . . ? C10 C9 C8 121.4(2) . . ? C10 C9 H9 117.4(14) . . ? C8 C9 H9 121.1(14) . . ? C9 C10 C5 117.3(2) . . ? C9 C10 H10 122.8(15) . . ? C5 C10 H10 119.4(15) . . ? C1 N1 C5 115.76(14) . . ? C1 N1 H1N1 121.3(14) . . ? C5 N1 H1N1 122.8(14) . . ? C3 N3 H1N3 123.7(14) . . ? C3 N3 H2N3 117.4(15) . . ? H1N3 N3 H2N3 119(2) . . ? C1 S1 C6 90.95(8) . . ? C3 S2 H1N1 86.6(5) . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.334(2) . ? C1 C2 1.402(2) . ? C1 S1 1.7406(15) . ? C2 C4 1.420(2) . ? C2 C3 1.437(2) . ? C3 N3 1.331(2) . ? C3 S2 1.6902(15) . ? C4 N2 1.142(2) . ? C5 C10 1.386(2) . ? C5 C6 1.390(2) . ? C5 N1 1.390(2) . ? C6 C7 1.386(3) . ? C6 S1 1.7473(18) . ? C7 C8 1.380(3) . ? C7 H7 0.94(3) . ? C8 C9 1.387(3) . ? C8 H8 0.87(3) . ? C9 C10 1.375(3) . ? C9 H9 0.93(2) . ? C10 H10 0.94(3) . ? N1 H1N1 0.83(2) . ? N3 H1N3 0.84(2) . ? N3 H2N3 0.85(2) . ? S2 H1N1 2.31(2) . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N1 S2 0.83(2) 2.31(2) 2.9599(16) 135.9(17) . N3 H1N3 N2 0.84(2) 2.26(2) 3.022(2) 150.1(19) 3_767