#------------------------------------------------------------------------------ #$Date: 2014-07-11 20:42:32 +0300 (Fri, 11 Jul 2014) $ #$Revision: 120074 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/02/32/4023260.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_4023260 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_volume 73 _journal_year 2008 _chemical_formula_moiety 'C7 H9 N3 O S' _chemical_formula_sum 'C7 H9 N3 O S' _chemical_formula_weight 183.23 _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 98.9720(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 10.2996(7) _cell_length_b 7.2768(5) _cell_length_c 12.6450(8) _cell_measurement_reflns_used 5103 _cell_measurement_temperature 295(1) _cell_measurement_theta_max 28.01 _cell_measurement_theta_min 2.38 _cell_volume 936.12(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 0.0204 _diffrn_reflns_av_sigmaI/netI 0.0149 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 10014 _diffrn_reflns_theta_full 26.99 _diffrn_reflns_theta_max 26.99 _diffrn_reflns_theta_min 2.00 _exptl_absorpt_coefficient_mu 0.303 _exptl_absorpt_correction_T_max 0.9419 _exptl_absorpt_correction_T_min 0.8961 _exptl_absorpt_correction_type none _exptl_crystal_colour light _exptl_crystal_density_diffrn 1.300 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 384 _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.253 _refine_diff_density_min -0.245 _refine_diff_density_rms 0.053 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.164 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 119 _refine_ls_number_reflns 2046 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.164 _refine_ls_R_factor_all 0.0567 _refine_ls_R_factor_gt 0.0542 _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^)+(0.0644P)^2^+0.3524P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1369 _refine_ls_wR_factor_ref 0.1389 _reflns_number_gt 1942 _reflns_number_total 2046 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file jo7022262-File003.cif _[local]_cod_data_source_block bashir2m _[local]_cod_cif_authors_sg_H-M 'P 21/c' _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_database_code 4023260 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 0.22885(18) 0.5749(3) 0.60569(16) 0.0476(5) Uani 1 1 d . . . C2 C 0.24054(18) 0.6833(3) 0.51759(15) 0.0452(4) Uani 1 1 d . . . C3 C 0.13525(19) 0.8131(3) 0.49169(16) 0.0524(5) Uani 1 1 d . . . C4 C 0.34744(19) 0.6759(3) 0.46055(15) 0.0455(4) Uani 1 1 d . . . C5 C 0.2852(2) 0.3391(4) 0.7447(2) 0.0664(7) Uani 1 1 d . . . H5 H 0.2196 0.4034 0.7794 0.080 Uiso 1 1 calc R . . C6 C 0.2308(3) 0.1535(5) 0.7086(3) 0.1063(12) Uani 1 1 d . . . H6A H 0.1507 0.1690 0.6592 0.159 Uiso 1 1 calc R . . H6B H 0.2132 0.0845 0.7695 0.159 Uiso 1 1 calc R . . H6C H 0.2936 0.0886 0.6740 0.159 Uiso 1 1 calc R . . C7 C 0.4108(3) 0.3247(5) 0.8243(2) 0.0858(9) Uani 1 1 d . . . H7A H 0.4754 0.2579 0.7927 0.129 Uiso 1 1 calc R . . H7B H 0.3934 0.2615 0.8872 0.129 Uiso 1 1 calc R . . H7C H 0.4434 0.4458 0.8435 0.129 Uiso 1 1 calc R . . N1 N 0.30942(18) 0.4480(3) 0.65238(15) 0.0578(5) Uani 1 1 d . . . H1N1 H 0.374(2) 0.420(3) 0.6234(19) 0.052(6) Uiso 1 1 d . . . N2 N 0.43473(18) 0.6671(3) 0.41539(16) 0.0634(5) Uani 1 1 d . . . N3 N 0.04299(19) 0.7848(3) 0.55632(17) 0.0692(6) Uani 1 1 d . . . H1N3 H -0.005(3) 0.865(4) 0.568(2) 0.068(8) Uiso 1 1 d . . . O1 O 0.12500(16) 0.9337(3) 0.42234(12) 0.0670(5) Uani 1 1 d . . . S1 S 0.08485(6) 0.62807(10) 0.65432(5) 0.0697(3) 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 0.0409(9) 0.0549(11) 0.0498(10) 0.0051(8) 0.0156(8) 0.0147(8) C2 0.0403(9) 0.0543(11) 0.0430(9) 0.0044(8) 0.0126(7) 0.0149(8) C3 0.0468(10) 0.0666(13) 0.0467(10) 0.0103(9) 0.0167(8) 0.0205(9) C4 0.0443(10) 0.0499(11) 0.0434(10) 0.0039(8) 0.0102(8) 0.0138(8) C5 0.0642(13) 0.0728(16) 0.0678(14) 0.0260(12) 0.0279(11) 0.0270(12) C6 0.084(2) 0.105(3) 0.123(3) 0.043(2) -0.004(2) -0.0197(18) C7 0.105(2) 0.0822(19) 0.0658(16) 0.0153(14) -0.0013(15) 0.0109(16) N1 0.0506(9) 0.0661(12) 0.0620(11) 0.0199(9) 0.0257(8) 0.0267(9) N2 0.0536(10) 0.0767(13) 0.0655(11) 0.0082(10) 0.0272(9) 0.0203(9) N3 0.0580(11) 0.0863(15) 0.0709(12) 0.0330(11) 0.0338(9) 0.0412(11) O1 0.0672(9) 0.0838(11) 0.0563(9) 0.0275(8) 0.0296(7) 0.0393(9) S1 0.0594(4) 0.0843(5) 0.0744(4) 0.0352(3) 0.0386(3) 0.0363(3) 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' 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 129.17(18) . . ? N1 C1 S1 120.71(15) . . ? C2 C1 S1 110.12(13) . . ? C1 C2 C4 124.24(16) . . ? C1 C2 C3 113.61(16) . . ? C4 C2 C3 122.08(17) . . ? O1 C3 N3 122.96(18) . . ? O1 C3 C2 127.41(18) . . ? N3 C3 C2 109.63(17) . . ? N2 C4 C2 178.8(2) . . ? N1 C5 C6 110.2(2) . . ? N1 C5 C7 109.5(2) . . ? C6 C5 C7 112.3(2) . . ? N1 C5 H5 108.3 . . ? C6 C5 H5 108.3 . . ? C7 C5 H5 108.3 . . ? 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 . . ? C1 N1 C5 124.25(18) . . ? C1 N1 H1N1 117.6(16) . . ? C5 N1 H1N1 117.8(16) . . ? C3 N3 S1 114.85(14) . . ? C3 N3 H1N3 121(2) . . ? S1 N3 H1N3 117(2) . . ? N3 S1 C1 91.44(9) . . ? 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 1.318(2) . ? C1 C2 1.386(3) . ? C1 S1 1.7356(18) . ? C2 C4 1.408(3) . ? C2 C3 1.437(3) . ? C3 O1 1.233(3) . ? C3 N3 1.362(3) . ? C4 N2 1.140(3) . ? C5 N1 1.464(3) . ? C5 C6 1.506(5) . ? C5 C7 1.514(4) . ? 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 . ? N1 H1N1 0.83(3) . ? N3 S1 1.690(2) . ? N3 H1N3 0.80(3) . ? 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 N3 H1N3 O1 0.80(3) 1.93(3) 2.722(2) 173(3) 3_576 N1 H1N1 N2 0.83(3) 2.19(3) 3.014(2) 167(2) 3_666 _journal_paper_doi 10.1021/jo7022262