#------------------------------------------------------------------------------ #$Date: 2016-02-14 14:26:36 +0000 (Sun, 14 Feb 2016) $ #$Revision: 176435 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/88/2008815.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_2008815 loop_ _publ_author_name 'Itoh, Kuniaki' 'Nishikawa, Kazuyoshi' 'Hashimoto, Masao' 'Yamada, Hiroaki' _publ_section_title ; 2,11-Dithia[3.3.1]paracyclophane, (I), and 2,11-dithia[3.3.2]paracyclophane, (II) ; _journal_issue 8 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1357 _journal_page_last 1360 _journal_paper_doi 10.1107/S0108270199004503 _journal_volume 55 _journal_year 1999 _chemical_formula_moiety 'C23 H22 S2' _chemical_formula_sum 'C23 H22 S2' _chemical_formula_weight 362.55 _chemical_melting_point 492.8(4) _chemical_name_common 2,11-dithia[3.3.1]paracyclophane _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' _audit_creation_method 'from TEXRAY.INF file' _cell_angle_alpha 90 _cell_angle_beta 105.716(8) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.565(2) _cell_length_b 10.7840(10) _cell_length_c 14.5120(10) _cell_measurement_reflns_used 25 _cell_measurement_temperature 296.2 _cell_measurement_theta_max 15.0 _cell_measurement_theta_min 13.9 _cell_volume 1892.9(4) _computing_cell_refinement ; MSC/AFC Diffractometer Control Software ; _computing_data_collection ; MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1988) ; _computing_data_reduction ; TEXSAN (Molecular Structure Corporation, 1992) ; _computing_publication_material TEXSAN _computing_structure_refinement TEXSAN _computing_structure_solution 'SIR88 (Burla et al., 1989)' _diffrn_ambient_temperature 296.2 _diffrn_measurement_device 'Rigaku AFC5R' _diffrn_measurement_method \w-2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_reflns_av_R_equivalents 0.0170 _diffrn_reflns_av_sigmaI/netI 0.074 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 4772 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_reflns_theta_max 27.49 _diffrn_reflns_theta_min 2.39 _diffrn_standards_decay_% none _diffrn_standards_interval_count 150 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.284 _exptl_absorpt_correction_T_max 0.905 _exptl_absorpt_correction_T_min 0.873 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details ' (North et al., 1968)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.272 _exptl_crystal_density_meas 1.23 _exptl_crystal_density_method flotation _exptl_crystal_description prismatic _exptl_crystal_F_000 768.00 _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.35 _refine_diff_density_max 0.26 _refine_diff_density_min -0.30 _refine_ls_extinction_coef 0.055(3) _refine_ls_extinction_method 'Zachariasen (1967)' _refine_ls_goodness_of_fit_obs 1.341 _refine_ls_hydrogen_treatment noref _refine_ls_matrix_type full _refine_ls_number_constraints 0 _refine_ls_number_parameters 227 _refine_ls_number_reflns 2880 _refine_ls_number_restraints 0 _refine_ls_R_factor_obs 0.0613 _refine_ls_shift/esd_max 0.0038 _refine_ls_shift/esd_mean 0.0002 _refine_ls_structure_factor_coef F _refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.00042|Fo|^2^]' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_obs 0.0535 _reflns_number_observed 2880 _reflns_number_total 4574 _reflns_observed_criterion I>\s(I) _cod_data_source_file ob1006.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '492.3-493.2' was changed to '492.8(4)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '492.3-493.2' was changed to '492.8(4)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'w = 1/[\s^2^(Fo) + 0.00042|Fo|^2^]' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/[\s^2^(Fo) + 0.00042|Fo|^2^]'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_cell_volume 1892.8(3) _cod_original_sg_symbol_H-M 'P 21/n' _cod_original_formula_sum 'C23 H22 S2 ' _cod_database_code 2008815 loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' 1/2-x,1/2+y,1/2-z ' -x, -y, -z' 1/2+x,1/2-y,1/2+z 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 0.1128(7) 0.0524(4) 0.0736(6) 0.0354(5) 0.0356(5) 0.0152(4) S2 0.0827(6) 0.0396(4) 0.1049(7) -0.0092(4) .0348(5) -0.0218(4) C1 0.070(2) 0.072(2) 0.068(2) 0.026(2) 0.030(2) 0.004(2) C2 0.051(2) 0.0510(10) 0.0460(10) 0.0080(10) 0.0210(10) 0.0050(10) C3 0.051(2) 0.0450(10) 0.0450(10) 0.0060(10) 0.0070(10) -0.0060(10) C4 0.0440(10) 0.0460(10) 0.053(2) 0.0080(10) 0.0080(10) -0.0030(10) C5 0.057(2) 0.0450(10) 0.047(2) -0.0050(10) .0190(10) -0.0050(10) C6 0.054(2) 0.067(2) 0.059(2) -0.0140(10) .0100(10) -0.0120(10) C7 0.0380(10) 0.079(2) 0.066(2) 0.0030(10) 0.0100(10) 0.005(2) C8 0.080(2) 0.058(2) 0.065(2) -0.004(2) .029(2) -0.0190(10) C9 0.085(2) 0.051(2) 0.098(2) 0.015(2) 0.040(2) -0.011(2) C10 0.057(2) 0.0450(10) 0.068(2) 0.0170(10) 0.0230(10) 0.0050(10) C11 0.072(2) 0.053(2) 0.081(2) 0.0000(10) 0.037(2) 0.006(2) C12 0.068(2) 0.073(2) 0.059(2) 0.003(2) 0.032(2) 0.007(2) C13 0.0390(10) 0.066(2) 0.047(2) 0.0070(10) 0.0050(10) 0.0060(10) C14 0.0370(10) 0.070(2) 0.059(2) 0.0040(10) 0.0110(10) 0.0070(10) C15 0.047(2) 0.063(2) 0.058(2) 0.0170(10) 0.0220(10) 0.0120(10) C16 0.047(2) 0.098(2) 0.053(2) -0.002(2) .0020(10) -0.010(2) C17 0.049(2) 0.069(2) 0.0420(10) -0.0120(10) .0080(10) -0.0170(10) C18 0.066(2) 0.069(2) 0.043(2) -0.006(2) 0.0150(10) 0.0020(10) C19 0.067(2) 0.075(2) 0.052(2) -0.001(2) .027(2) -0.011(2) C20 0.085(2) 0.047(2) 0.061(2) 0.000(2) 0.029(2) -0.0170(10) C21 0.094(2) 0.046(2) 0.068(2) -0.016(2) .028(2) -0.0090(10) C22 0.064(2) 0.074(2) 0.060(2) -0.028(2) .026(2) -0.020(2) C23 0.122(3) 0.057(2) 0.092(2) 0.027(2) 0.044(2) -0.013(2) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom _atom_site_refinement_flags _atom_site_occupancy S1 0.23288(8) 0.35550(7) 0.10647(6) 0.0776(3) Uani d . . 1.00 S2 0.38706(7) -0.34955(7) 0.01606(7) 0.0739(3) Uani d . . 1.00 C1 0.1740(2) 0.2036(3) 0.1112(2) 0.0679(10) Uani d . . 1.00 C2 0.2240(2) 0.1000(2) 0.0676(2) 0.0479(7) Uani d . . 1.00 C3 0.3358(2) 0.0718(2) 0.1003(2) 0.0484(7) Uani d . . 1.00 C4 0.3804(2) -0.0255(2) 0.0627(2) 0.0490(7) Uani d . . 1.00 C5 0.3156(2) -0.0999(2) -0.0083(2) 0.0488(8) Uani d . . 1.00 C6 0.2046(2) -0.0716(3) -0.0416(2) 0.0613(9) Uani d . . 1.00 C7 0.1603(2) 0.0277(3) -0.0039(2) 0.0619(9) Uani d . . 1.00 C8 0.3649(2) -0.2052(3) -0.0518(2) 0.0662(9) Uani d . . 1.00 C9 0.5336(3) -0.3448(3) 0.0762(2) 0.0750(10) Uani d . . 1.00 C10 0.5682(2) -0.2517(2) 0.1560(2) 0.0555(8) Uani d . . 1.00 C11 0.5184(2) -0.2490(3) 0.2306(2) 0.0654(10) Uani d . . 1.00 C12 0.5448(2) -0.1595(3) 0.3001(2) 0.0637(9) Uani d . . 1.00 C13 0.6231(2) -0.0688(3) 0.2998(2) 0.0521(8) Uani d . . 1.00 C14 0.6749(2) -0.0742(3) 0.2273(2) 0.0556(8) Uani d . . 1.00 C15 0.6475(2) -0.1643(3) 0.1562(2) 0.0546(8) Uani d . . 1.00 C16 0.6443(2) 0.0332(3) 0.3736(2) 0.0683(9) Uani d . . 1.00 C17 0.5584(2) 0.1346(3) 0.3470(2) 0.0545(8) Uani d . . 1.00 C18 0.4621(2) 0.1309(3) 0.3757(2) 0.0592(9) Uani d . . 1.00 C19 0.3783(2) 0.2168(3) 0.3422(2) 0.0626(9) Uani d . . 1.00 C20 0.3885(3) 0.3090(3) 0.2793(2) 0.0626(9) Uani d . . 1.00 C21 0.4872(3) 0.3177(3) 0.2543(2) 0.0690(10) Uani d . . 1.00 C22 0.5702(2) 0.2325(3) 0.2874(2) 0.0643(10) Uani d . . 1.00 C23 0.2935(3) 0.3924(3) 0.2326(2) 0.0870(10) Uani d . . 1.00 H1 0.1787 0.1896 0.1725 0.0714 Uiso calc . . 1.00 H2 0.0948 0.2094 0.0731 0.0811 Uiso calc . . 1.00 H3 0.3815 0.1190 0.1493 0.0538 Uiso calc . . 1.00 H4 0.4572 -0.0464 0.0873 0.0511 Uiso calc . . 1.00 H5 0.1568 -0.1194 -0.0925 0.0885 Uiso calc . . 1.00 H6 0.0897 0.0437 -0.0279 0.0680 Uiso calc . . 1.00 H7 0.3149 -0.2271 -0.1138 0.0919 Uiso calc . . 1.00 H8 0.4367 -0.1823 -0.0599 0.0808 Uiso calc . . 1.00 H9 0.5480 -0.4277 0.1011 0.0963 Uiso calc . . 1.00 H10 0.5720 -0.3313 0.0295 0.0777 Uiso calc . . 1.00 H11 0.4627 -0.3081 0.2294 0.0969 Uiso calc . . 1.00 H12 0.5081 -0.1563 0.3466 0.0708 Uiso calc . . 1.00 H13 0.7310 -0.0118 0.2269 0.0609 Uiso calc . . 1.00 H14 0.6833 -0.1646 0.1056 0.0613 Uiso calc . . 1.00 H15 0.7150 0.0702 0.3780 0.0698 Uiso calc . . 1.00 H16 0.6457 -0.0029 0.4351 0.0821 Uiso calc . . 1.00 H17 0.4524 0.0655 0.4124 0.0702 Uiso calc . . 1.00 H18 0.3108 0.2130 0.3614 0.0793 Uiso calc . . 1.00 H19 0.4949 0.3831 0.2086 0.0987 Uiso calc . . 1.00 H20 0.6365 0.2394 0.2698 0.0764 Uiso calc . . 1.00 H21 0.2375 0.3932 0.2611 0.0862 Uiso calc . . 1.00 H22 0.3185 0.4822 0.2296 0.1464 Uiso calc . . 1.00 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; S 0.125 0.123 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -3 0 -1 -2 0 -2 -1 0 -3 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C1 S1 C23 102.8(2) yes C8 S2 C9 102.9(2) yes S1 C1 C2 115.8(2) yes S1 C1 H1 106.0 no S1 C1 H2 106.2 no C2 C1 H1 111.9 no C2 C1 H2 106.3 no H1 C1 H2 110.6 no C1 C2 C3 121.2(2) yes C1 C2 C7 121.2(2) yes C3 C2 C7 117.6(2) no C2 C3 C4 121.0(2) no C2 C3 H3 119.8 no C4 C3 H3 119.1 no C3 C4 C5 121.3(2) no C3 C4 H4 120.6 no C5 C4 H4 118.0 no C4 C5 C6 117.9(2) no C4 C5 C8 121.5(2) yes C6 C5 C8 120.6(2) yes C5 C6 C7 120.5(2) no C5 C6 H5 120.7 no C7 C6 H5 118.8 no C2 C7 C6 121.6(2) no C2 C7 H6 120.6 no C6 C7 H6 117.8 no S2 C8 C5 115.6(2) yes S2 C8 H7 105.6 no S2 C8 H8 105.2 no C5 C8 H7 109.4 no C5 C8 H8 111.0 no H7 C8 H8 109.6 no S2 C9 C10 115.7(2) yes S2 C9 H9 102.6 no S2 C9 H10 108.0 no C10 C9 H9 110.1 no C10 C9 H10 110.6 no H9 C9 H10 109.4 no C9 C10 C11 121.1(3) yes C9 C10 C15 121.3(3) yes C11 C10 C15 117.6(3) no C10 C11 C12 121.2(3) no C10 C11 H11 117.4 no C12 C11 H11 121.3 no C11 C12 C13 121.6(2) no C11 C12 H12 120.0 no C13 C12 H12 118.3 no C12 C13 C14 117.0(3) no C12 C13 C16 120.0(2) yes C14 C13 C16 122.9(3) yes C13 C14 C15 121.5(2) no C13 C14 H13 117.8 no C15 C14 H13 120.7 no C10 C15 C14 121.0(2) no C10 C15 H14 119.1 no C14 C15 H14 119.9 no C13 C16 C17 111.7(2) yes C13 C16 H15 109.4 no C13 C16 H16 108.4 no C17 C16 H15 107.5 no C17 C16 H16 111.1 no H15 C16 H16 108.7 no C16 C17 C18 121.7(3) yes C16 C17 C22 121.1(2) yes C18 C17 C22 117.1(3) no C17 C18 C19 121.2(3) no C17 C18 H17 117.7 no C19 C18 H17 120.8 no C18 C19 C20 121.0(3) no C18 C19 H18 120.9 no C20 C19 H18 118.0 no C19 C20 C21 118.2(3) no C19 C20 C23 121.7(3) yes C21 C20 C23 119.9(3) yes C20 C21 C22 120.7(3) no C20 C21 H19 118.7 no C22 C21 H19 120.5 no C17 C22 C21 121.6(3) no C17 C22 H20 118.6 no C21 C22 H20 119.8 no S1 C23 C20 112.7(2) yes S1 C23 H21 106.8 no S1 C23 H22 102.3 no C20 C23 H21 114.8 no C20 C23 H22 111.8 no H21 C23 H22 107.2 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S1 C1 . . 1.806(3) yes S1 C23 . . 1.826(3) yes S2 C8 . . 1.825(3) yes S2 C9 . . 1.812(3) yes C1 C2 . . 1.504(3) yes C2 C3 . . 1.389(3) no C2 C7 . . 1.369(4) no C3 C4 . . 1.371(3) no C4 C5 . . 1.383(3) no C5 C6 . . 1.381(4) no C5 C8 . . 1.511(3) yes C6 C7 . . 1.386(4) no C9 C10 . . 1.505(4) yes C10 C11 . . 1.390(4) no C10 C15 . . 1.371(4) no C11 C12 . . 1.370(4) no C12 C13 . . 1.388(4) no C13 C14 . . 1.379(3) no C13 C16 . . 1.509(4) yes C14 C15 . . 1.391(4) no C16 C17 . . 1.511(4) yes C17 C18 . . 1.383(4) no C17 C22 . . 1.395(4) no C18 C19 . . 1.388(4) no C19 C20 . . 1.378(4) no C20 C21 . . 1.387(4) no C20 C23 . . 1.502(4) yes C21 C22 . . 1.375(4) no C1 H1 . . 0.888 no C1 H2 . . 1.000 no C3 H3 . . 0.934 no C4 H4 . . 0.961 no C6 H5 . . 0.965 no C7 H6 . . 0.878 no C8 H7 . . 0.977 no C8 H8 . . 0.972 no C9 H9 . . 0.963 no C9 H10 . . 0.944 no C11 H11 . . 0.944 no C12 H12 . . 0.916 no C14 H13 . . 0.976 no C15 H14 . . 0.960 no C16 H15 . . 0.960 no C16 H16 . . 0.970 no C18 H17 . . 0.912 no C19 H18 . . 0.962 no C21 H19 . . 0.990 no C22 H20 . . 0.938 no C23 H21 . . 0.908 no C23 H22 . . 1.023 no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_2 _geom_contact_publ_flag S1 C16 3.473(3) 4_454 no C15 C22 3.595(4) 2_645 no