#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/88/2008816.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_2008816 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 'C24 H24 S2' _chemical_formula_sum 'C24 H24 S2' _chemical_formula_weight 376.57 _chemical_melting_point 435.9(3) _chemical_name_common 2,11-dithia[3.3.2]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 105.570(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 14.345(3) _cell_length_b 7.585(3) _cell_length_c 19.248(2) _cell_measurement_reflns_used 23 _cell_measurement_temperature 298.2 _cell_measurement_theta_max 14.8 _cell_measurement_theta_min 13.3 _cell_volume 2017.5(9) _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 ; DIRDIF92 (PATTY; Beurskens et al., 1992) ; _diffrn_ambient_temperature 298.2 _diffrn_measurement_device 'Rigaku AFC5R' _diffrn_measurement_method \w-2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.5418 _diffrn_reflns_av_R_equivalents 0.0151 _diffrn_reflns_av_sigmaI/netI 0.046 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 2966 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_reflns_theta_max 60.08 _diffrn_reflns_theta_min 3.20 _diffrn_standards_decay_% 4.1 _diffrn_standards_interval_count 150 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 2.401 _exptl_absorpt_correction_T_max 0.698 _exptl_absorpt_correction_T_min 0.478 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details ' (North et al., 1968)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.240 _exptl_crystal_density_meas 1.20 _exptl_crystal_density_method flotation _exptl_crystal_description prismatic _exptl_crystal_F_000 800.00 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _refine_diff_density_max 0.19 _refine_diff_density_min -0.21 _refine_ls_extinction_coef 0.059(4) _refine_ls_extinction_method 'Zachariasen (1967)' _refine_ls_goodness_of_fit_obs 1.484 _refine_ls_hydrogen_treatment noref _refine_ls_matrix_type full _refine_ls_number_constraints 0 _refine_ls_number_parameters 236 _refine_ls_number_reflns 2182 _refine_ls_number_restraints 0 _refine_ls_R_factor_obs 0.0421 _refine_ls_shift/esd_max 0.0005 _refine_ls_shift/esd_mean 0.0001 _refine_ls_structure_factor_coef F _refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.00029|Fo|^2^]' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_obs 0.0444 _reflns_number_observed 2182 _reflns_number_total 2863 _reflns_observed_criterion >sigma(I) _cod_data_source_file ob1006.cif _cod_data_source_block II _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '435.7-436.2' was changed to '435.9(3)' - 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 '435.7-436.2' was changed to '435.9(3)' - 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) + 0.00029|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) + 0.00029|Fo|^2^]'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_cell_volume 2017.4(9) _cod_original_sg_symbol_H-M 'P 21/n' _cod_original_formula_sum 'C24 H24 S2 ' _cod_database_code 2008816 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 0.0684(5) 0.0470(6) 0.0519(4) 0.0009(4) 0.0106(4) 0.0113(4) S2 0.0580(5) 0.0560(6) 0.0472(4) -0.0056(4) -0.0075(3) 0.0074(4) C1 0.055(2) 0.066(2) 0.046(2) 0.003(2) 0.0150(10) 0.006(2) C2 0.043(2) 0.041(2) 0.0440(10) 0.0060(10) 0.0110(10) 0.0060(10) C3 0.0380(10) 0.044(2) 0.055(2) 0.0010(10) 0.0110(10) 0.008(2) C4 0.040(2) 0.042(2) 0.050(2) -0.0010(10) .0010(10) -0.0010(10) C5 0.046(2) 0.034(2) 0.0420(10) 0.0070(10) 0.0060(10) 0.0020(10) C6 0.050(2) 0.061(2) 0.044(2) -0.009(2) 0.0090(10) 0.008(2) C7 0.054(2) 0.062(2) 0.0400(10) -0.017(2) 0.0040(10) 0.003(2) C8 0.068(2) 0.049(2) 0.042(2) 0.006(2) 0.0090(10) 0.0000(10) C9 0.079(2) 0.065(2) 0.040(2) -0.017(2) 0.0060(10) 0.005(2) C10 0.058(2) 0.045(2) 0.0330(10) -0.0070(10) 0.0100(10) 0.0050(10) C11 0.050(2) 0.048(2) 0.050(2) 0.0020(10) 0.0050(10) 0.004(2) C12 0.055(2) 0.045(2) 0.045(2) 0.0020(10) 0.0100(10) 0.0010(10) C13 0.048(2) 0.041(2) 0.0410(10) -0.0080(10) 0.0090(10) 0.0060(10) C14 0.045(2) 0.063(2) 0.054(2) -0.005(2) 0.0160(10) 0.003(2) C15 0.064(2) 0.057(2) 0.049(2) -0.005(2) .0270(10) -0.004(2) C16 0.064(2) 0.050(2) 0.049(2) -0.017(2) 0.0060(10) 0.001(2) C17 0.046(2) 0.074(3) 0.049(2) -0.016(2) 0.0020(10) 0.008(2) C18 0.0360(10) 0.053(2) 0.0380(10) -0.0040(10) 0.0010(10) 0.0010(10) C19 0.053(2) 0.051(2) 0.050(2) -0.005(2) .0100(10) -0.007(2) C20 0.053(2) 0.056(2) 0.044(2) -0.002(2) .0180(10) -0.012(2) C21 0.046(2) 0.052(2) 0.0330(10) -0.0010(10) 0.0030(10) 0.0000(10) C22 0.057(2) 0.065(2) 0.064(2) 0.016(2) 0.020(2) 0.012(2) C23 0.048(2) 0.072(3) 0.059(2) 0.010(2) 0.0220(10) 0.006(2) C24 0.062(2) 0.065(2) 0.038(2) -0.003(2) 0.0090(10) 0.008(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 -0.17392(6) 0.34080(10) -0.12994(4) 0.0568(3) Uani d . . 1.00 S2 0.02195(5) -0.00900(10) 0.27585(4) 0.0579(2) Uani d . . 1.00 C1 -0.0754(2) 0.2035(4) -0.07850(10) 0.0552(10) Uani d . . 1.00 C2 -0.0675(2) 0.1966(4) 0.00100(10) 0.0429(8) Uani d . . 1.00 C3 0.0069(2) 0.2800(4) 0.0507(2) 0.0462(9) Uani d . . 1.00 C4 0.0138(2) 0.2735(4) 0.12360(10) 0.0463(9) Uani d . . 1.00 C5 -0.0534(2) 0.1826(4) 0.14880(10) 0.0420(8) Uani d . . 1.00 C6 -0.1280(2) 0.0983(4) 0.09930(10) 0.0525(9) Uani d . . 1.00 C7 -0.1342(2) 0.1050(4) 0.02650(10) 0.0537(9) Uani d . . 1.00 C8 -0.0476(2) 0.1761(4) 0.22820(10) 0.0540(9) Uani d . . 1.00 C9 -0.0720(2) -0.1521(4) 0.29130(10) 0.0630(10) Uani d . . 1.00 C10 -0.1409(2) -0.2261(4) 0.22430(10) 0.0458(9) Uani d . . 1.00 C11 -0.1089(2) -0.3389(4) 0.17920(10) 0.0508(9) Uani d . . 1.00 C12 -0.1718(2) -0.4061(4) 0.11700(10) 0.0488(9) Uani d . . 1.00 C13 -0.2691(2) -0.3624(4) 0.09850(10) 0.0440(8) Uani d . . 1.00 C14 -0.3012(2) -0.2485(4) 0.14350(10) 0.0531(9) Uani d . . 1.00 C15 -0.2377(2) -0.1812(4) 0.20540(10) 0.0544(10) Uani d . . 1.00 C16 -0.3366(2) -0.4485(4) 0.03350(10) 0.0562(10) Uani d . . 1.00 C17 -0.4094(2) -0.3279(4) -0.01650(10) 0.0584(10) Uani d . . 1.00 C18 -0.3684(2) -0.1942(4) -0.05820(10) 0.0440(9) Uani d . . 1.00 C19 -0.3044(2) -0.2442(4) -0.09710(10) 0.0519(9) Uani d . . 1.00 C20 -0.2710(2) -0.1220(4) -0.13860(10) 0.0497(9) Uani d . . 1.00 C21 -0.2989(2) 0.0520(4) -0.14240(10) 0.0451(9) Uani d . . 1.00 C22 -0.3638(2) 0.1027(4) -0.1040(2) 0.0610(10) Uani d . . 1.00 C23 -0.3968(2) -0.0203(5) -0.0629(2) 0.0580(10) Uani d . . 1.00 C24 -0.2584(2) 0.1832(4) -0.18460(10) 0.0559(10) Uani d . . 1.00 H1 -0.0187 0.2437 -0.0876 0.0715 Uiso calc . . 1.00 H2 -0.0830 0.0916 -0.1001 0.0702 Uiso calc . . 1.00 H3 0.0556 0.3399 0.0338 0.0719 Uiso calc . . 1.00 H4 0.0674 0.3374 0.1571 0.0587 Uiso calc . . 1.00 H5 -0.1781 0.0359 0.1153 0.0783 Uiso calc . . 1.00 H6 -0.1912 0.0544 -0.0058 0.0991 Uiso calc . . 1.00 H7 -0.0186 0.2891 0.2499 0.0903 Uiso calc . . 1.00 H8 -0.1151 0.1743 0.2371 0.0672 Uiso calc . . 1.00 H9 -0.0380 -0.2360 0.3187 0.1066 Uiso calc . . 1.00 H10 -0.1085 -0.0945 0.3223 0.1130 Uiso calc . . 1.00 H11 -0.0390 -0.3740 0.1913 0.0690 Uiso calc . . 1.00 H12 -0.1458 -0.4842 0.0834 0.1141 Uiso calc . . 1.00 H13 -0.3707 -0.2139 0.1280 0.0908 Uiso calc . . 1.00 H14 -0.2603 -0.1115 0.2315 0.0753 Uiso calc . . 1.00 H15 -0.2976 -0.5224 0.0024 0.0713 Uiso calc . . 1.00 H16 -0.3707 -0.5486 0.0506 0.0917 Uiso calc . . 1.00 H17 -0.4530 -0.2628 0.0115 0.0787 Uiso calc . . 1.00 H18 -0.4556 -0.3969 -0.0503 0.0782 Uiso calc . . 1.00 H19 -0.2828 -0.3584 -0.0969 0.1060 Uiso calc . . 1.00 H20 -0.2247 -0.1584 -0.1647 0.0742 Uiso calc . . 1.00 H21 -0.3850 0.2105 -0.1049 0.1659 Uiso calc . . 1.00 H22 -0.4403 0.0265 -0.0369 0.0923 Uiso calc . . 1.00 H23 -0.3066 0.2721 -0.2155 0.0964 Uiso calc . . 1.00 H24 -0.2238 0.1283 -0.2156 0.0661 Uiso calc . . 1.00 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0.018 0.009 ;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 0.333 0.557 ;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 -1 -2 3 -1 -1 3 -1 0 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 C24 103.70(10) yes C8 S2 C9 102.30(10) yes S1 C1 C2 114.2(2) yes S1 C1 H1 107.6 no S1 C1 H2 107.2 no C2 C1 H1 111.8 no C2 C1 H2 112.7 no H1 C1 H2 102.5 no C1 C2 C3 121.4(3) yes C1 C2 C7 120.7(2) yes C3 C2 C7 117.9(2) no C2 C3 C4 121.2(2) no C2 C3 H3 118.8 no C4 C3 H3 120.0 no C3 C4 C5 120.7(2) no C3 C4 H4 118.5 no C5 C4 H4 120.8 no C4 C5 C6 118.4(2) yes C4 C5 C8 121.3(2) yes C6 C5 C8 120.3(2) yes C5 C6 C7 120.6(3) no C5 C6 H5 120.4 no C7 C6 H5 119.0 no C2 C7 C6 121.2(3) no C2 C7 H6 121.6 no C6 C7 H6 116.8 no S2 C8 C5 114.2(2) yes S2 C8 H7 110.0 no S2 C8 H8 108.6 no C5 C8 H7 107.5 no C5 C8 H8 111.8 no H7 C8 H8 104.4 no S2 C9 C10 115.3(2) yes S2 C9 H9 102.2 no S2 C9 H10 111.7 no C10 C9 H9 111.9 no C10 C9 H10 110.3 no H9 C9 H10 104.7 no C9 C10 C11 121.1(3) yes C9 C10 C15 121.0(3) yes C11 C10 C15 117.9(3) no C10 C11 C12 121.4(3) no C10 C11 H11 119.9 no C12 C11 H11 118.7 no C11 C12 C13 120.8(3) no C11 C12 H12 119.7 no C13 C12 H12 119.4 no C12 C13 C14 117.9(2) no C12 C13 C16 119.2(3) yes C14 C13 C16 122.7(2) yes C13 C14 C15 121.0(3) no C13 C14 H13 116.8 no C15 C14 H13 122.2 no C10 C15 C14 121.1(3) no C10 C15 H14 120.9 no C14 C15 H14 117.9 no C13 C16 C17 116.3(3) yes C13 C16 H15 111.7 no C13 C16 H16 108.3 no C17 C16 H15 109.4 no C17 C16 H16 110.5 no H15 C16 H16 99.2 no C16 C17 C18 116.2(2) yes C16 C17 H17 111.2 no C16 C17 H18 109.6 no C18 C17 H17 109.1 no C18 C17 H18 107.7 no H17 C17 H18 102.0 no C17 C18 C19 120.9(3) yes C17 C18 C23 121.9(3) yes C19 C18 C23 117.0(3) no C18 C19 C20 120.6(3) no C18 C19 H19 121.9 no C20 C19 H19 117.5 no C19 C20 C21 122.1(3) no C19 C20 H20 119.7 no C21 C20 H20 118.2 no C20 C21 C22 117.6(3) no C20 C21 C24 121.2(3) yes C22 C21 C24 121.1(3) yes C21 C22 C23 119.9(3) no C21 C22 H21 121.9 no C23 C22 H21 118.2 no C18 C23 C22 122.8(3) no C18 C23 H22 122.7 no C22 C23 H22 114.5 no S1 C24 C21 114.7(2) yes S1 C24 H23 98.2 no S1 C24 H24 105.5 no C21 C24 H23 116.8 no C21 C24 H24 112.7 no H23 C24 H24 107.5 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 . . 1.819(3) yes S1 C24 . . 1.822(3) yes S2 C8 . . 1.821(3) yes S2 C9 . . 1.816(3) yes C1 C2 . . 1.505(3) yes C2 C3 . . 1.380(4) no C2 C7 . . 1.375(4) no C3 C4 . . 1.381(4) no C4 C5 . . 1.375(4) no C5 C6 . . 1.383(4) no C5 C8 . . 1.509(3) yes C6 C7 . . 1.382(4) yes C9 C10 . . 1.506(4) yes C10 C11 . . 1.382(4) no C10 C15 . . 1.380(4) no C11 C12 . . 1.388(4) no C12 C13 . . 1.384(4) no C13 C14 . . 1.387(4) no C13 C16 . . 1.510(4) yes C14 C15 . . 1.389(4) yes C16 C17 . . 1.520(4) yes C17 C18 . . 1.508(4) no C18 C19 . . 1.384(4) no C18 C23 . . 1.376(4) no C19 C20 . . 1.390(4) no C20 C21 . . 1.375(4) no C21 C22 . . 1.390(4) no C21 C24 . . 1.497(4) yes C22 C23 . . 1.387(4) yes C1 H1 . . 0.929 no C1 H2 . . 0.939 no C3 H3 . . 0.960 no C4 H4 . . 0.988 no C6 H5 . . 0.977 no C7 H6 . . 0.964 no C8 H7 . . 0.994 no C8 H8 . . 1.029 no C9 H9 . . 0.885 no C9 H10 . . 0.994 no C11 H11 . . 1.003 no C12 H12 . . 1.020 no C14 H13 . . 0.997 no C15 H14 . . 0.850 no C16 H15 . . 1.080 no C16 H16 . . 1.006 no C17 H17 . . 1.051 no C17 H18 . . 0.952 no C19 H19 . . 0.920 no C20 H20 . . 0.975 no C22 H21 . . 0.871 no C23 H22 . . 0.966 no C24 H23 . . 1.032 no C24 H24 . . 0.967 no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_2 S2 C19 3.524(3) 4_545 C2 C2 3.561(5) 3_555 C4 C12 3.583(4) 1_565 C5 C12 3.526(4) 1_565 loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21136227 2 PubChem 100949824