#------------------------------------------------------------------------------ #$Date: 2012-02-03 19:16:24 +0200 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/52/2015230.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_2015230 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 'C10 H16 N2 S2' _chemical_formula_moiety 'C10 H16 N2 S2' _chemical_formula_sum 'C10 H16 N2 S2' _chemical_formula_weight 228.37 _chemical_name_common ; cyclooctanespiro-4'-imidazolidine-2',5'-dithione ; _chemical_name_systematic ; 1,3-diazaspiro[4.7]dodecane-2,4-dithione ; _space_group_IT_number 61 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M 'P b c a' _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 8 _cell_length_a 8.484(2) _cell_length_b 11.5018(18) _cell_length_c 23.992(10) _cell_measurement_reflns_used 22 _cell_measurement_temperature 290(2) _cell_measurement_theta_max 19.07 _cell_measurement_theta_min 17.92 _cell_volume 2341.2(12) _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 0.0605 _diffrn_reflns_av_sigmaI/netI 0.0438 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_number 10820 _diffrn_reflns_theta_full 27.98 _diffrn_reflns_theta_max 27.98 _diffrn_reflns_theta_min 1.70 _diffrn_standards_decay_% 5 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.420 _exptl_absorpt_correction_type none _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.296 _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'square prism' _exptl_crystal_F_000 976 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.36 _refine_diff_density_max 0.609 _refine_diff_density_min -0.341 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 136 _refine_ls_number_reflns 2812 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.016 _refine_ls_R_factor_all 0.1007 _refine_ls_R_factor_gt 0.0571 _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^)+(0.0826P)^2^+1.3610P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1463 _refine_ls_wR_factor_ref 0.1743 _reflns_number_gt 1730 _reflns_number_total 2812 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file bm1624.cif _[local]_cod_data_source_block IV _cod_database_code 2015230 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' '-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 -3 0 4 -3 1 -3 -2 -3 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' 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 _atom_site_disorder_assembly _atom_site_disorder_group N N1 0.9007(3) 0.3404(2) 0.55765(10) 0.0476(6) Uani d . 1 . . H H1 0.9930 0.3099 0.5553 0.057 Uiso calc R 1 . . N N3 0.6569(3) 0.3784(2) 0.54033(11) 0.0540(7) Uani d . 1 . . H H3 0.5666 0.3754 0.5241 0.065 Uiso calc R 1 . . S S1 0.78194(9) 0.21329(8) 0.47347(4) 0.0576(3) Uani d . 1 . . S S2 0.56062(11) 0.53474(10) 0.61389(5) 0.0818(4) Uani d . 1 . . C C2 0.7837(3) 0.3117(3) 0.52427(12) 0.0455(7) Uani d . 1 . . C C4 0.6874(3) 0.4488(3) 0.58401(14) 0.0522(7) Uani d . 1 . . C C5 0.8598(3) 0.4289(3) 0.59923(12) 0.0442(7) Uani d . 1 . . C C6 0.9603(4) 0.5383(3) 0.58883(14) 0.0544(8) Uani d . 1 . . H H6A 1.0686 0.5136 0.5834 0.065 Uiso calc R 1 . . H H6B 0.9254 0.5731 0.5541 0.065 Uiso calc R 1 . . C C7 0.9597(5) 0.6322(3) 0.6330(2) 0.0774(11) Uani d . 1 . . H H7A 0.8638 0.6250 0.6547 0.093 Uiso calc R 1 . . H H7B 0.9572 0.7074 0.6147 0.093 Uiso calc R 1 . . C C8 1.1020(8) 0.6293(5) 0.6732(2) 0.121(2) Uani d . 1 C . H H8A 1.1958 0.6365 0.6503 0.145 Uiso calc R 1 . . H H8B 1.0960 0.6993 0.6956 0.145 Uiso calc R 1 . . C C9 1.1285(8) 0.5374(5) 0.7098(2) 0.120(2) Uani d . 1 . . H H9A 1.0354 0.5280 0.7328 0.144 Uiso calc R 1 A 1 H H9B 1.2148 0.5587 0.7342 0.144 Uiso calc R 1 A 1 C C10 1.1667(9) 0.4217(7) 0.6837(4) 0.0784(18) Uani d P 0.62 C 1 H H10A 1.2479 0.3848 0.7060 0.094 Uiso calc PR 0.62 C 1 H H10B 1.2113 0.4360 0.6471 0.094 Uiso calc PR 0.62 C 1 C C101 1.1092(18) 0.4142(12) 0.7190(5) 0.088(4) Uani d P 0.38 C 2 H H10C 1.0508 0.4056 0.7535 0.105 Uiso calc PR 0.38 C 2 H H10D 1.2135 0.3827 0.7257 0.105 Uiso calc PR 0.38 C 2 C C11 1.0316(5) 0.3359(4) 0.67705(17) 0.0783(12) Uani d . 1 . . H H11A 1.0663 0.2767 0.6510 0.094 Uiso calc R 1 B 1 H H11B 1.0174 0.2978 0.7128 0.094 Uiso calc R 1 B 1 C C12 0.8699(4) 0.3769(3) 0.65781(13) 0.0586(8) Uani d . 1 C . H H12A 0.8324 0.4346 0.6841 0.070 Uiso calc R 1 . . H H12B 0.7982 0.3113 0.6596 0.070 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 N1 0.0265(11) 0.0625(15) 0.0540(14) 0.0049(11) -0.0022(10) -0.0135(12) N3 0.0252(11) 0.0704(17) 0.0665(17) 0.0039(11) -0.0033(11) -0.0144(14) S1 0.0307(4) 0.0809(6) 0.0611(5) -0.0017(4) 0.0000(3) -0.0244(4) S2 0.0446(5) 0.0897(8) 0.1112(9) 0.0120(4) 0.0123(5) -0.0378(6) C2 0.0293(12) 0.0595(17) 0.0477(15) -0.0046(12) 0.0044(11) -0.0043(13) C4 0.0342(14) 0.0606(18) 0.0617(19) -0.0008(13) 0.0056(13) -0.0088(15) C5 0.0323(13) 0.0523(16) 0.0481(16) -0.0002(12) 0.0022(11) -0.0063(13) C6 0.0472(17) 0.0610(19) 0.0550(18) -0.0025(14) 0.0010(14) 0.0031(15) C7 0.067(2) 0.060(2) 0.106(3) -0.0034(18) 0.013(2) -0.008(2) C8 0.146(5) 0.109(4) 0.108(4) -0.031(4) -0.045(4) -0.021(3) C9 0.145(5) 0.107(4) 0.107(4) -0.020(4) -0.066(4) -0.017(3) C10 0.066(4) 0.088(5) 0.081(5) 0.009(4) -0.025(4) 0.000(4) C101 0.099(10) 0.109(10) 0.055(6) 0.000(8) -0.023(7) -0.010(7) C11 0.102(3) 0.070(2) 0.063(2) 0.010(2) -0.023(2) 0.0038(19) C12 0.066(2) 0.0577(19) 0.0520(18) -0.0127(17) 0.0064(15) 0.0003(15) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag N1 C2 1.317(3) yes N1 C5 1.467(4) yes N1 H1 0.8600 ? N3 C4 1.350(4) yes N3 C2 1.376(4) yes N3 H3 0.8600 ? S1 C2 1.664(3) yes S2 C4 1.627(3) yes C4 C5 1.525(4) yes C5 C12 1.530(4) ? C5 C6 1.540(4) ? C6 C7 1.513(5) ? C6 H6A 0.9700 ? C6 H6B 0.9700 ? C7 C8 1.544(6) ? C7 H7A 0.9700 ? C7 H7B 0.9700 ? C8 C9 1.392(7) ? C8 H8A 0.9700 ? C8 H8B 0.9700 ? C12 C11 1.522(5) ? C12 H12A 0.9700 ? C12 H12B 0.9700 ? C9 C10 1.507(9) ? C9 C101 1.444(15) ? C9 H9A 0.9700 ? C9 H9B 0.9700 ? C11 C10 1.520(9) ? C11 C101 1.501(12) ? C11 H11A 0.9700 ? C11 H11B 0.9700 ? C10 H10A 0.9700 ? C10 H10B 0.9700 ? C101 H10C 0.9700 ? C101 H10D 0.9700 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C2 N1 C5 114.1(2) C2 N1 H1 122.9 C5 N1 H1 122.9 C4 N3 C2 113.7(2) C4 N3 H3 123.2 C2 N3 H3 123.2 N1 C2 N3 106.2(2) N1 C2 S1 128.5(2) N3 C2 S1 125.2(2) N3 C4 C5 106.3(2) N3 C4 S2 125.4(2) C5 C4 S2 128.3(2) N1 C5 C4 99.7(2) N1 C5 C12 109.9(2) C4 C5 C12 109.4(2) N1 C5 C6 109.0(2) C4 C5 C6 111.7(3) C12 C5 C6 116.0(3) C7 C6 C5 117.9(3) C7 C6 H6A 107.8 C5 C6 H6A 107.8 C7 C6 H6B 107.8 C5 C6 H6B 107.8 H6A C6 H6B 107.2 C6 C7 C8 114.7(4) C6 C7 H7A 108.6 C8 C7 H7A 108.6 C6 C7 H7B 108.6 C8 C7 H7B 108.6 H7A C7 H7B 107.6 C9 C8 C7 122.4(5) C9 C8 H8A 106.7 C7 C8 H8A 106.7 C9 C8 H8B 106.7 C7 C8 H8B 106.7 H8A C8 H8B 106.6 C11 C12 C5 116.7(3) C11 C12 H12A 108.1 C5 C12 H12A 108.1 C11 C12 H12B 108.1 C5 C12 H12B 108.1 H12A C12 H12B 107.3 C8 C9 C101 145.4(6) C8 C9 C10 116.3(6) C8 C9 H9A 108.2 C101 C9 H9A 73.2 C10 C9 H9A 108.2 C8 C9 H9B 108.2 C101 C9 H9B 103.9 C10 C9 H9B 108.2 H9A C9 H9B 107.4 C101 C11 C12 114.4(6) C12 C11 C10 120.7(4) C101 C11 H11A 136.0 C12 C11 H11A 107.2 C10 C11 H11A 107.2 C101 C11 H11B 74.6 C12 C11 H11B 107.2 C10 C11 H11B 107.2 H11A C11 H11B 106.8 C9 C10 C11 117.1(6) C9 C10 H10A 108.0 C11 C10 H10A 108.0 C9 C10 H10B 108.0 C11 C10 H10B 108.0 H10A C10 H10B 107.3 C9 C101 C11 122.4(9) C9 C101 H10C 106.7 C11 C101 H10C 106.7 C9 C101 H10D 106.7 C11 C101 H10D 106.7 H10C C101 H10D 106.6 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 C5 C6 C7 C8 98.5(4) C6 C7 C8 C9 -64.9(7) C7 C8 C9 C10 65.9(9) C8 C9 C10 C11 -97.4(8) C9 C10 C11 C12 41.5(8) 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 3_556 0.86 2.56 3.376(2) 159 yes N3 H3 S1 3_456 0.86 2.62 3.367(3) 146 yes