#------------------------------------------------------------------------------ #$Date: 2008-02-29 13:03:34 +0200 (Fri, 29 Feb 2008) $ #$Revision: 179 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2015229.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_2015229 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 'C9 H14 N2 S2' _chemical_formula_moiety 'C9 H14 N2 S2' _chemical_formula_sum 'C9 H14 N2 S2' _chemical_formula_weight 214.34 _chemical_name_common ; cycloheptanespiro-4'-imidazolidine-2',5'-dithione ; _chemical_name_systematic ; 1,3-diazaspiro[4.6]undecane-2,4-dithione ; _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M ' P 21/n' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 105.848(19) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.4041(14) _cell_length_b 17.859(4) _cell_length_c 8.4491(14) _cell_measurement_reflns_used 22 _cell_measurement_temperature 290(2) _cell_measurement_theta_max 19.8 _cell_measurement_theta_min 18.4 _cell_volume 1074.7(4) _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_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 0.0232 _diffrn_reflns_av_sigmaI/netI 0.0273 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 5464 _diffrn_reflns_theta_full 27.97 _diffrn_reflns_theta_max 27.97 _diffrn_reflns_theta_min 2.28 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 500 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.452 _exptl_absorpt_correction_type none _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.325 _exptl_crystal_density_method 'not measured' _exptl_crystal_description cube _exptl_crystal_F_000 456 _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.33 _refine_diff_density_max 0.204 _refine_diff_density_min -0.258 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 118 _refine_ls_number_reflns 2591 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.002 _refine_ls_R_factor_all 0.0480 _refine_ls_R_factor_gt 0.0337 _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^)+(0.0458P)^2^+0.2540P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0842 _refine_ls_wR_factor_ref 0.0914 _reflns_number_gt 2042 _reflns_number_total 2591 _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+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 2 -1 -3 0 -5 -2 1 -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 S S1 0.54858(6) 0.45898(3) 0.26027(5) 0.04001(13) Uani d . 1 S S2 -0.00067(7) 0.63319(3) -0.09273(5) 0.05107(16) Uani d . 1 N N1 0.29715(19) 0.55459(8) 0.32787(15) 0.0346(3) Uani d . 1 H H1 0.3315 0.5462 0.4321 0.042 Uiso calc R 1 N N3 0.2837(2) 0.54828(8) 0.06919(15) 0.0351(3) Uani d . 1 H H3 0.3135 0.5355 -0.0186 0.042 Uiso calc R 1 C C2 0.3755(2) 0.52184(8) 0.22362(18) 0.0305(3) Uani d . 1 C C4 0.1426(2) 0.59606(9) 0.06924(18) 0.0319(3) Uani d . 1 C C5 0.1453(2) 0.60684(8) 0.24953(17) 0.0295(3) Uani d . 1 C C6 0.2080(2) 0.68680(9) 0.3080(2) 0.0400(4) Uani d . 1 H H6A 0.2752 0.6845 0.4239 0.048 Uiso calc R 1 H H6B 0.2962 0.7038 0.2493 0.048 Uiso calc R 1 C C7 0.0543(3) 0.74498(10) 0.2863(3) 0.0530(5) Uani d . 1 H H7A -0.0421 0.7345 0.1852 0.064 Uiso calc R 1 H H7B 0.1065 0.7939 0.2750 0.064 Uiso calc R 1 C C8 -0.0363(3) 0.74755(12) 0.4289(3) 0.0626(6) Uani d . 1 H H8A 0.0627 0.7506 0.5312 0.075 Uiso calc R 1 H H8B -0.1099 0.7931 0.4192 0.075 Uiso calc R 1 C C9 -0.1618(3) 0.68186(12) 0.4400(3) 0.0576(5) Uani d . 1 H H9A -0.2727 0.6841 0.3470 0.069 Uiso calc R 1 H H9B -0.2026 0.6874 0.5391 0.069 Uiso calc R 1 C C10 -0.0725(3) 0.60469(11) 0.4424(2) 0.0464(4) Uani d . 1 H H10A -0.1526 0.5677 0.4735 0.056 Uiso calc R 1 H H10B 0.0473 0.6043 0.5256 0.056 Uiso calc R 1 C C11 -0.0414(2) 0.58219(9) 0.2773(2) 0.0361(4) Uani d . 1 H H11A -0.1425 0.6031 0.1901 0.043 Uiso calc R 1 H H11B -0.0500 0.5281 0.2677 0.043 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 0.0452(3) 0.0481(3) 0.0278(2) 0.01627(19) 0.01183(17) 0.00268(16) S2 0.0536(3) 0.0663(3) 0.0295(2) 0.0192(2) 0.00480(19) 0.0103(2) N1 0.0402(8) 0.0432(7) 0.0204(6) 0.0115(6) 0.0083(5) 0.0017(5) N3 0.0403(7) 0.0456(8) 0.0209(6) 0.0089(6) 0.0108(5) 0.0020(5) C2 0.0347(8) 0.0334(7) 0.0241(7) 0.0000(6) 0.0092(6) -0.0005(5) C4 0.0351(8) 0.0343(8) 0.0267(7) 0.0002(6) 0.0092(6) 0.0017(6) C5 0.0333(8) 0.0319(7) 0.0231(6) 0.0027(6) 0.0074(6) 0.0003(6) C6 0.0386(9) 0.0365(8) 0.0457(9) -0.0045(7) 0.0129(7) -0.0076(7) C7 0.0595(12) 0.0335(9) 0.0691(13) 0.0026(8) 0.0230(10) -0.0004(9) C8 0.0683(14) 0.0515(12) 0.0734(15) 0.0134(10) 0.0289(12) -0.0165(10) C9 0.0592(13) 0.0692(13) 0.0531(11) 0.0139(11) 0.0301(10) -0.0058(10) C10 0.0535(11) 0.0538(11) 0.0387(9) 0.0004(9) 0.0242(8) 0.0021(8) C11 0.0389(9) 0.0367(9) 0.0350(8) -0.0018(7) 0.0140(7) -0.0009(6) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag S1 C2 1.6676(16) yes S2 C4 1.6263(16) yes N1 C2 1.3169(19) yes N1 C5 1.4717(19) yes N1 H1 0.8600 ? N3 C4 1.349(2) yes N3 C2 1.3795(19) yes N3 H3 0.8600 ? C4 C5 1.530(2) yes C5 C11 1.529(2) ? C5 C6 1.541(2) ? C6 C7 1.515(2) ? C6 H6A 0.9700 ? C6 H6B 0.9700 ? C7 C8 1.532(3) ? C7 H7A 0.9700 ? C7 H7B 0.9700 ? C8 C9 1.515(3) ? C8 H8A 0.9700 ? C8 H8B 0.9700 ? C9 C10 1.526(3) ? C9 H9A 0.9700 ? C9 H9B 0.9700 ? C10 C11 1.528(2) ? C10 H10A 0.9700 ? C10 H10B 0.9700 ? C11 H11A 0.9700 ? C11 H11B 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 113.75(12) C2 N1 H1 123.1 C5 N1 H1 123.1 C4 N3 C2 113.45(13) C4 N3 H3 123.3 C2 N3 H3 123.3 N3 C4 C5 106.27(12) N3 C4 S2 125.79(12) C5 C4 S2 127.93(12) N1 C2 N3 106.69(13) N1 C2 S1 129.15(12) N3 C2 S1 124.15(11) N1 C5 C11 111.11(13) N1 C5 C4 99.72(12) C11 C5 C4 110.48(13) N1 C5 C6 108.49(13) C11 C5 C6 115.05(13) C4 C5 C6 110.91(13) C7 C6 C5 116.51(14) C7 C6 H6A 108.2 C5 C6 H6A 108.2 C7 C6 H6B 108.2 C5 C6 H6B 108.2 H6A C6 H6B 107.3 C6 C7 C8 113.66(17) C6 C7 H7A 108.8 C8 C7 H7A 108.8 C6 C7 H7B 108.8 C8 C7 H7B 108.8 H7A C7 H7B 107.7 C9 C8 C7 115.66(17) C9 C8 H8A 108.4 C7 C8 H8A 108.4 C9 C8 H8B 108.4 C7 C8 H8B 108.4 H8A C8 H8B 107.4 C8 C9 C10 115.44(17) C8 C9 H9A 108.4 C10 C9 H9A 108.4 C8 C9 H9B 108.4 C10 C9 H9B 108.4 H9A C9 H9B 107.5 C9 C10 C11 113.44(15) C9 C10 H10A 108.9 C11 C10 H10A 108.9 C9 C10 H10B 108.9 C11 C10 H10B 108.9 H10A C10 H10B 107.7 C10 C11 C5 115.62(14) C10 C11 H11A 108.4 C5 C11 H11A 108.4 C10 C11 H11B 108.4 C5 C11 H11B 108.4 H11A C11 H11B 107.4 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 86.0(2) C6 C7 C8 C9 -71.7(3) C7 C8 C9 C10 53.5(3) C8 C9 C10 C11 -70.9(2) 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_666 0.86 2.51 3.3618(14) 172 yes N3 H3 S1 3_665 0.86 2.52 3.3460(15) 161 yes