#------------------------------------------------------------------------------ #$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $ #$Revision: 202017 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/20/56/7205692.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_7205692 loop_ _publ_author_name 'Lenthall, Joseph T.' 'Foster, Jonathan A.' 'Anderson, Kirsty M.' 'Probert, Michael R.' 'Howard, Judith A. K.' 'Steed, Jonathan W.' _publ_section_title ; Hydrogen bonding interactions with the thiocarbonyl \p-system ; _journal_issue 9 _journal_name_full CrystEngComm _journal_page_first 3202 _journal_paper_doi 10.1039/c0ce00680g _journal_volume 13 _journal_year 2011 _chemical_formula_moiety 'C11 H17 N3 S' _chemical_formula_sum 'C11 H17 N3 S' _chemical_formula_weight 223.34 _chemical_name_systematic ; ? ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 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 109.7120(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 10.6285(4) _cell_length_b 9.7517(4) _cell_length_c 12.8232(5) _cell_measurement_temperature 120(2) _cell_volume 1251.19(9) _computing_cell_refinement SMART _computing_data_collection SMART _computing_data_reduction SAINT _computing_molecular_graphics XP _computing_publication_material XP _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 120(2) _diffrn_measured_fraction_theta_full 0.917 _diffrn_measured_fraction_theta_max 0.917 _diffrn_measurement_device_type 'SMART 1k' _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 0.0598 _diffrn_reflns_av_sigmaI/netI 0.0428 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 11735 _diffrn_reflns_theta_full 30.42 _diffrn_reflns_theta_max 30.42 _diffrn_reflns_theta_min 2.16 _exptl_absorpt_coefficient_mu 0.233 _exptl_absorpt_correction_T_max 0.959 _exptl_absorpt_correction_T_min 0.948 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details SADABS _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.186 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 480 _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.18 _refine_diff_density_max 0.331 _refine_diff_density_min -0.319 _refine_diff_density_rms 0.050 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 144 _refine_ls_number_reflns 3477 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.042 _refine_ls_R_factor_all 0.0494 _refine_ls_R_factor_gt 0.0373 _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^)+(0.0427P)^2^+0.3752P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0922 _refine_ls_wR_factor_ref 0.0982 _reflns_number_gt 2825 _reflns_number_total 3477 _reflns_threshold_expression >2sigma(I) _cod_data_source_file c0ce00680g.txt _cod_data_source_block 06srv197 _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 1555 2011-01-17 13:19:09Z saulius ; _cod_original_sg_symbol_H-M P21/n _cod_database_code 7205692 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -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 S1 S 0.34849(3) 0.90144(3) 0.06016(3) 0.02076(10) Uani 1 1 d . . . N1 N 0.60786(10) 0.85756(11) 0.11123(9) 0.0197(2) Uani 1 1 d . . . H1N H 0.6063 0.9365 0.0776 0.024 Uiso 1 1 calc R . . N2 N 0.50344(11) 0.70530(11) 0.19046(10) 0.0223(2) Uani 1 1 d . . . H2N H 0.5828 0.6663 0.2129 0.027 Uiso 1 1 calc R . . N3 N 0.77433(15) 0.84851(16) 0.33966(11) 0.0355(3) Uani 1 1 d . . . C1 C 0.73142(12) 0.78342(12) 0.14731(10) 0.0182(2) Uani 1 1 d . . . C2 C 0.77600(13) 0.72130(14) 0.06879(11) 0.0233(3) Uani 1 1 d . . . H2 H 0.7249 0.7300 -0.0076 0.028 Uiso 1 1 calc R . . C3 C 0.89406(14) 0.64670(15) 0.10018(12) 0.0276(3) Uani 1 1 d . . . H3 H 0.9256 0.6070 0.0460 0.033 Uiso 1 1 calc R . . C4 C 0.96544(13) 0.63110(14) 0.21242(12) 0.0251(3) Uani 1 1 d . . . H4 H 1.0442 0.5766 0.2351 0.030 Uiso 1 1 calc R . . C5 C 0.92326(13) 0.69369(14) 0.29106(11) 0.0246(3) Uani 1 1 d . . . H5 H 0.9734 0.6814 0.3673 0.030 Uiso 1 1 calc R . . C6 C 0.80767(13) 0.77538(13) 0.26091(11) 0.0214(3) Uani 1 1 d . . . C7 C 0.49304(12) 0.81499(12) 0.12512(10) 0.0176(2) Uani 1 1 d . . . C8 C 0.40322(13) 0.63870(13) 0.23120(11) 0.0208(3) Uani 1 1 d . . . C9 C 0.29245(16) 0.57360(16) 0.13491(13) 0.0328(3) Uani 1 1 d . . . H9A H 0.2436 0.6455 0.0838 0.049 Uiso 1 1 calc R . . H9B H 0.2308 0.5240 0.1635 0.049 Uiso 1 1 calc R . . H9C H 0.3319 0.5096 0.0957 0.049 Uiso 1 1 calc R . . C10 C 0.34572(16) 0.74034(15) 0.29325(12) 0.0303(3) Uani 1 1 d . . . H10A H 0.4185 0.7806 0.3546 0.045 Uiso 1 1 calc R . . H10B H 0.2835 0.6927 0.3225 0.045 Uiso 1 1 calc R . . H10C H 0.2982 0.8131 0.2426 0.045 Uiso 1 1 calc R . . C11 C 0.48098(16) 0.52821(16) 0.31223(14) 0.0353(4) Uani 1 1 d . . . H11A H 0.5518 0.5714 0.3734 0.053 Uiso 1 1 calc R . . H11B H 0.5209 0.4639 0.2736 0.053 Uiso 1 1 calc R . . H11C H 0.4201 0.4786 0.3416 0.053 Uiso 1 1 calc R . . H3N H 0.801(2) 0.814(2) 0.4081(19) 0.051(6) Uiso 1 1 d . . . H4N H 0.704(2) 0.8971(19) 0.3193(15) 0.035(5) Uiso 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 S1 0.01679(16) 0.02006(15) 0.02312(16) 0.00464(11) 0.00368(12) 0.00038(11) N1 0.0181(5) 0.0180(5) 0.0220(5) 0.0063(4) 0.0054(4) -0.0002(4) N2 0.0187(5) 0.0186(5) 0.0320(6) 0.0082(4) 0.0119(5) 0.0029(4) N3 0.0365(8) 0.0459(8) 0.0208(6) -0.0021(6) 0.0052(5) 0.0161(6) C1 0.0159(5) 0.0182(5) 0.0199(6) 0.0037(4) 0.0052(5) -0.0011(4) C2 0.0229(6) 0.0274(6) 0.0197(6) 0.0022(5) 0.0074(5) -0.0014(5) C3 0.0275(7) 0.0314(7) 0.0277(7) 0.0005(6) 0.0145(6) 0.0029(6) C4 0.0189(6) 0.0252(6) 0.0323(7) 0.0068(5) 0.0099(5) 0.0025(5) C5 0.0207(6) 0.0280(6) 0.0224(6) 0.0058(5) 0.0036(5) 0.0005(5) C6 0.0218(6) 0.0224(6) 0.0194(6) 0.0017(5) 0.0061(5) -0.0008(5) C7 0.0189(6) 0.0152(5) 0.0180(5) -0.0003(4) 0.0052(5) -0.0011(4) C8 0.0223(6) 0.0173(5) 0.0267(6) 0.0025(5) 0.0136(5) 0.0000(5) C9 0.0399(8) 0.0278(7) 0.0338(8) -0.0056(6) 0.0165(7) -0.0151(6) C10 0.0408(8) 0.0275(7) 0.0289(7) -0.0008(5) 0.0199(7) 0.0046(6) C11 0.0344(8) 0.0283(7) 0.0486(9) 0.0189(7) 0.0211(7) 0.0065(6) 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 C7 N1 C1 124.79(10) . . ? C7 N1 H1N 117.6 . . ? C1 N1 H1N 117.6 . . ? C7 N2 C8 130.65(11) . . ? C7 N2 H2N 114.7 . . ? C8 N2 H2N 114.7 . . ? C6 N3 H3N 116.8(13) . . ? C6 N3 H4N 118.9(12) . . ? H3N N3 H4N 117.9(18) . . ? C2 C1 C6 120.48(12) . . ? C2 C1 N1 119.08(11) . . ? C6 C1 N1 120.44(11) . . ? C3 C2 C1 120.99(12) . . ? C3 C2 H2 119.5 . . ? C1 C2 H2 119.5 . . ? C2 C3 C4 118.81(13) . . ? C2 C3 H3 120.6 . . ? C4 C3 H3 120.6 . . ? C5 C4 C3 120.72(13) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C4 C5 C6 121.36(12) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? N3 C6 C5 120.63(12) . . ? N3 C6 C1 121.90(12) . . ? C5 C6 C1 117.41(12) . . ? N2 C7 N1 115.99(11) . . ? N2 C7 S1 124.84(10) . . ? N1 C7 S1 119.17(9) . . ? N2 C8 C10 111.18(11) . . ? N2 C8 C9 110.26(11) . . ? C10 C8 C9 110.93(12) . . ? N2 C8 C11 105.04(11) . . ? C10 C8 C11 108.87(12) . . ? C9 C8 C11 110.40(12) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? 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 S1 C7 1.7034(13) . ? N1 C7 1.3564(16) . ? N1 C1 1.4323(16) . ? N1 H1N 0.8800 . ? N2 C7 1.3402(15) . ? N2 C8 1.4848(16) . ? N2 H2N 0.8800 . ? N3 C6 1.3767(18) . ? N3 H3N 0.89(2) . ? N3 H4N 0.85(2) . ? C1 C2 1.3882(18) . ? C1 C6 1.4101(17) . ? C2 C3 1.3874(19) . ? C2 H2 0.9500 . ? C3 C4 1.391(2) . ? C3 H3 0.9500 . ? C4 C5 1.377(2) . ? C4 H4 0.9500 . ? C5 C6 1.4047(18) . ? C5 H5 0.9500 . ? C8 C10 1.5222(18) . ? C8 C9 1.527(2) . ? C8 C11 1.5311(19) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 30653757