#------------------------------------------------------------------------------ #$Date: 2011-09-17 23:27:16 +0300 (Sat, 17 Sep 2011) $ #$Revision: 26029 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2015227.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2015227 loop_ _publ_author_name 'Boris Shivachev' 'Rosica Petrova' 'Marin Marinov' 'Neyko Stoyanov' 'Anife Ahmedova' 'Mariana Mitewa' _publ_section_title ; Four cycloalkanespiro-4'-imidazolidine-2',5'-dithiones ; _journal_coeditor_code BM1624 _journal_issue 4 _journal_name_full 'Acta Crystallographica, Section C' _journal_page_first o211 _journal_page_last o215 _journal_volume 62 _journal_year 2006 _chemical_formula_iupac 'C7 H10 N2 S2' _chemical_formula_moiety 'C7 H10 N2 S2' _chemical_formula_sum 'C7 H10 N2 S2' _chemical_formula_weight 186.29 _chemical_melting_point 495 _chemical_name_common ; cyclopentanespiro-4'-imidazolidine-2',5'-dithione ; _chemical_name_systematic ; 1,3-diazaspiro[4.4]nonane-2,4-dithione ; _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.898(5) _cell_length_b 8.4607(19) _cell_length_c 13.587(2) _cell_measurement_reflns_used 22 _cell_measurement_temperature 290(2) _cell_measurement_theta_max 20.68 _cell_measurement_theta_min 20.25 _cell_volume 907.9(6) _computing_cell_refinement 'CAD-4 Express' _computing_data_collection 'CAD-4 Express (Enraf--Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_molecular_graphics ; Ortep-3 for Windows (Farrugia, 1997) and Mercury 1.4 (Bruno et al., 2002) ; _computing_publication_material 'WinGX (Farrugia, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 290(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf--Nonius CAD-4' _diffrn_measurement_method 'non-profiled omega/2theta 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 0.0564 _diffrn_reflns_av_sigmaI/netI 0.0619 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 2483 _diffrn_reflns_theta_full 27.96 _diffrn_reflns_theta_max 27.96 _diffrn_reflns_theta_min 2.84 _diffrn_standards_decay_% 2 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.524 _exptl_absorpt_correction_type none _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.363 _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'square prism' _exptl_crystal_F_000 392 _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.259 _refine_diff_density_min -0.287 _refine_ls_abs_structure_details 'Flack (1983), 911 Friedel pairs' _refine_ls_abs_structure_Flack 0.06(16) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 100 _refine_ls_number_reflns 2198 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.054 _refine_ls_R_factor_all 0.0849 _refine_ls_R_factor_gt 0.0509 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0446P)^2^+0.3808P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1118 _refine_ls_wR_factor_ref 0.1257 _reflns_number_gt 1629 _reflns_number_total 2198 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file bm1624.cif loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 0 -2 -3 3 -1 3 -2 -1 4 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_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy S S1 -0.08105(12) 0.14147(10) 0.73014(7) 0.0490(3) Uani d . 1 S S2 0.42294(17) 0.36691(13) 0.95075(10) 0.0758(4) Uani d . 1 N N1 0.1853(4) 0.0174(3) 0.8266(2) 0.0445(8) Uani d . 1 H H1 0.1597 -0.0787 0.8125 0.053 Uiso calc R 1 N N3 0.1704(4) 0.2716(3) 0.8361(2) 0.0364(6) Uani d . 1 H H3 0.1335 0.3658 0.8258 0.044 Uiso calc R 1 C C2 0.0955(4) 0.1392(4) 0.7984(2) 0.0338(6) Uani d . 1 C C4 0.3087(4) 0.2393(4) 0.8914(3) 0.0411(8) Uani d . 1 C C5 0.3338(4) 0.0617(4) 0.8848(3) 0.0366(7) Uani d . 1 C C6 0.4999(5) 0.0135(5) 0.8350(3) 0.0583(11) Uani d . 1 H H6A 0.4864 0.0103 0.7640 0.070 Uiso calc R 1 H H6B 0.5893 0.0878 0.8510 0.070 Uiso calc R 1 C C7 0.5410(7) -0.1478(6) 0.8742(4) 0.0899(17) Uani d . 1 H H7A 0.5127 -0.2278 0.8258 0.108 Uiso calc R 1 H H7B 0.6610 -0.1554 0.8887 0.108 Uiso calc R 1 C C8 0.4421(7) -0.1716(6) 0.9636(3) 0.0804(15) Uani d . 1 H H8A 0.5170 -0.1934 1.0185 0.096 Uiso calc R 1 H H8B 0.3670 -0.2614 0.9553 0.096 Uiso calc R 1 C C9 0.3411(5) -0.0266(4) 0.9840(3) 0.0465(9) Uani d . 1 H H9A 0.3957 0.0378 1.0338 0.056 Uiso calc R 1 H H9B 0.2282 -0.0538 1.0064 0.056 Uiso calc R 1 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 S1 0.0486(5) 0.0299(4) 0.0686(6) 0.0001(5) -0.0247(4) -0.0010(4) S2 0.0832(8) 0.0430(5) 0.1014(9) -0.0149(7) -0.0503(7) -0.0013(6) N1 0.0463(19) 0.0266(14) 0.061(2) 0.0025(13) -0.0171(16) -0.0035(13) N3 0.0395(16) 0.0238(12) 0.0460(15) -0.0011(11) -0.0064(13) -0.0004(12) C2 0.0351(15) 0.0288(14) 0.0376(16) -0.0035(17) -0.0030(13) 0.0001(14) C4 0.0425(19) 0.0331(16) 0.0476(19) -0.0061(14) -0.0060(19) 0.0056(18) C5 0.0330(16) 0.0325(15) 0.0442(19) 0.0004(13) -0.0074(18) 0.0022(16) C6 0.047(2) 0.064(3) 0.065(2) 0.012(2) 0.010(2) 0.008(2) C7 0.090(4) 0.075(3) 0.105(4) 0.046(3) 0.026(3) 0.015(3) C8 0.105(4) 0.063(3) 0.073(3) 0.044(3) 0.015(3) 0.016(2) C9 0.054(2) 0.0419(19) 0.044(2) 0.0103(18) -0.0008(18) 0.0049(16) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag C2 N1 1.309(4) yes C2 N3 1.366(4) yes C2 S1 1.674(3) yes C4 N3 1.353(4) yes C4 C5 1.519(4) yes C4 S2 1.622(4) yes C5 N1 1.463(4) yes C5 C6 1.532(5) ? C5 C9 1.543(5) ? C6 C7 1.500(6) ? C6 H6A 0.9700 ? C6 H6B 0.9700 ? C7 C8 1.458(6) ? C7 H7A 0.9700 ? C7 H7B 0.9700 ? C8 C9 1.490(5) ? C8 H8A 0.9700 ? C8 H8B 0.9700 ? C9 H9A 0.9700 ? C9 H9B 0.9700 ? N1 H1 0.8600 ? N3 H3 0.8600 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle N1 C2 N3 107.5(3) N1 C2 S1 128.5(3) N3 C2 S1 124.0(2) N3 C4 C5 105.8(3) N3 C4 S2 126.2(3) C5 C4 S2 128.0(3) N1 C5 C4 100.4(3) N1 C5 C6 112.3(3) C4 C5 C6 113.7(3) N1 C5 C9 112.2(3) C4 C5 C9 115.6(3) C6 C5 C9 103.0(3) C7 C6 C5 105.7(4) C7 C6 H6A 110.6 C5 C6 H6A 110.6 C7 C6 H6B 110.6 C5 C6 H6B 110.6 H6A C6 H6B 108.7 C8 C7 C6 107.8(4) C8 C7 H7A 110.1 C6 C7 H7A 110.1 C8 C7 H7B 110.1 C6 C7 H7B 110.1 H7A C7 H7B 108.5 C7 C8 C9 109.2(4) C7 C8 H8A 109.8 C9 C8 H8A 109.8 C7 C8 H8B 109.8 C9 C8 H8B 109.8 H8A C8 H8B 108.3 C8 C9 C5 104.8(3) C8 C9 H9A 110.8 C5 C9 H9A 110.8 C8 C9 H9B 110.8 C5 C9 H9B 110.8 H9A C9 H9B 108.9 C2 N1 C5 113.0(3) C2 N1 H1 123.5 C5 N1 H1 123.5 C4 N3 C2 113.1(3) C4 N3 H3 123.4 C2 N3 H3 123.4 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N1 H1 S1 4_546 0.86 2.51 3.375(3) 179 yes N3 H3 S1 4_556 0.86 2.49 3.332(3) 167 yes _cod_database_code 2015227