#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/01/2200122.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_2200122 loop_ _publ_author_name 'Mori, Akira' 'Kubo, Kanji' ' Yin, Bing Zhu' ' Takeshita, Hitoshi' _publ_section_title 2-(7-Isopropyl-2-methylcyclohepta[b]thiophen-8-ylidene)propanedinitrile _journal_issue 2 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o118 _journal_page_last o119 _journal_paper_doi 10.1107/S1600536801001064 _journal_volume 57 _journal_year 2001 _chemical_formula_iupac 'C16 H14 N2 S' _chemical_formula_moiety 'C16 H14 N2 S' _chemical_formula_sum 'C16 H14 N2 S' _chemical_formula_weight 266.35 _chemical_melting_point 107.5(5) _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yab' _symmetry_space_group_name_H-M 'P 1 21/a 1' _cell_angle_alpha 90.00 _cell_angle_beta 100.647(5) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 17.174(5) _cell_length_b 7.380(5) _cell_length_c 11.393(5) _cell_measurement_reflns_used 20 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 18.0 _cell_measurement_theta_min 10.1 _cell_volume 1419.1(12) _computing_cell_refinement ' CAD-4 Software' _computing_data_collection ' CAD-4 Software (Enraf-Nonius, 1989)' _computing_data_reduction ' MolEN (Fair, 1990)' _computing_molecular_graphics 'Xtal_GX (Hall & du Boulay, 1995)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution ' SIR97 (Altomare et al., 1997)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full .999 _diffrn_measured_fraction_theta_max .999 _diffrn_measurement_device_type 'Enraf-Nonius FR590' _diffrn_measurement_method \w-2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .0390 _diffrn_reflns_av_sigmaI/netI .1202 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 3016 _diffrn_reflns_theta_full 26.3 _diffrn_reflns_theta_max 26.29 _diffrn_reflns_theta_min 2.74 _diffrn_standards_decay_% .5 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .215 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min .959 _exptl_absorpt_correction_type '\y scan' _exptl_absorpt_process_details '(North et al., 1968)' _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.247 _exptl_crystal_density_meas ? _exptl_crystal_description prism _exptl_crystal_F_000 560 _exptl_crystal_size_max .27 _exptl_crystal_size_mid .27 _exptl_crystal_size_min .23 _refine_diff_density_max .275 _refine_diff_density_min -.287 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref .994 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 172 _refine_ls_number_reflns 2871 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all .994 _refine_ls_R_factor_all .172 _refine_ls_R_factor_gt .052 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean <0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0580P)^2^+0.0071P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .143 _reflns_number_gt 1396 _reflns_number_total 2871 _reflns_threshold_expression I>2\s(I) _cod_data_source_file cf6037.cif _cod_data_source_block 1 _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '107--108' was changed to '107.5(5)' - 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 '107--108' was changed to '107.5(5)' - 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: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_original_sg_symbol_H-M 'P 21/a' _cod_database_code 2200122 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' loop_ _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 _atom_site_type_symbol S1 .54532(5) .19535(14) .38292(8) .0499(3) Uani d . 1 . . S N1 .44857(17) .4131(4) .1162(3) .0595(9) Uani d . 1 . . N N2 .56520(17) .0975(4) -.1129(3) .0531(8) Uani d . 1 . . N C1 .62781(16) .1698(4) .1956(3) .0339(7) Uani d . 1 . . C C2 .62663(18) .2272(4) .3161(3) .0372(8) Uani d . 1 . . C C3 .68670(19) .3169(4) .3920(3) .0429(8) Uani d . 1 . . C C4 .7619(2) .3647(5) .3615(3) .0556(10) Uani d . 1 . . C H4 .7886 .4624 .4021 .067 Uiso calc R 1 . . H C5 .7970(2) .2827(5) .2808(4) .0580(10) Uani d . 1 . . C H5 .8433 .3353 .2653 .070 Uiso calc R 1 . . H C6 .77017(19) .1209(5) .2156(3) .0466(9) Uani d . 1 . . C H6 .8101 .0499 .1945 .056 Uiso calc R 1 . . H C7 .69612(18) .0557(5) .1802(3) .0397(8) Uani d . 1 . . C C8 .56826(17) .2091(4) .1019(3) .0336(7) Uani d . 1 . . C C9 .50189(19) .3232(5) .1128(3) .0408(8) Uani d . 1 . . C C10 .56775(17) .1473(4) -.0182(3) .0377(8) Uani d . 1 . . C C11 .5902(2) .3035(5) .5113(3) .0510(9) Uani d . 1 . . C C12 .6629(2) .3626(5) .5015(3) .0537(10) Uani d . 1 . . C H12 .6950 .4281 .5614 .064 Uiso calc R 1 . . H C13 .5474(3) .3181(6) .6143(3) .0746(13) Uani d . 1 . . C H13A .4963 .2620 .5933 .112 Uiso calc R 1 . . H H13B .5410 .4435 .6327 .112 Uiso calc R 1 . . H H13C .5775 .2581 .6827 .112 Uiso calc R 1 . . H C14 .6780(2) -.1343(5) .1325(3) .0519(10) Uani d . 1 . . C H14 .6393 -.1243 .0580 .062 Uiso calc R 1 . . H C15 .6399(2) -.2411(5) .2199(4) .0700(12) Uani d . 1 . . C H15A .6279 -.3612 .1895 .105 Uiso calc R 1 . . H H15B .5918 -.1821 .2305 .105 Uiso calc R 1 . . H H15C .6756 -.2480 .2953 .105 Uiso calc R 1 . . H C16 .7498(3) -.2352(6) .1047(4) .0858(14) Uani d . 1 . . C H16A .7729 -.1667 .0482 .129 Uiso calc R 1 . . H H16B .7335 -.3517 .0714 .129 Uiso calc R 1 . . H H16C .7881 -.2507 .1768 .129 Uiso calc R 1 . . H 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 .0486(5) .0622(6) .0414(5) -.0025(5) .0148(4) -.0051(5) N1 .0468(18) .067(2) .066(2) .0139(17) .0140(16) -.0020(18) N2 .059(2) .065(2) .0351(17) -.0014(16) .0070(14) .0021(16) C1 .0281(16) .0355(18) .0383(17) -.0053(14) .0066(14) .0011(15) C2 .0386(18) .0382(18) .0345(17) .0034(15) .0059(14) .0000(15) C3 .0451(19) .041(2) .0395(18) .0013(17) -.0013(15) .0010(17) C4 .047(2) .049(2) .063(3) -.0168(19) -.0068(19) .0000(19) C5 .034(2) .069(3) .070(3) -.009(2) .0083(19) .007(2) C6 .038(2) .055(2) .047(2) .0081(17) .0102(16) .0075(18) C7 .0332(18) .052(2) .0341(18) .0040(17) .0058(15) .0033(16) C8 .0284(16) .0376(18) .0355(17) -.0024(15) .0076(13) -.0012(15) C9 .0363(19) .045(2) .0404(18) .0005(17) .0060(15) -.0024(17) C10 .0299(17) .042(2) .039(2) .0012(15) .0003(15) .0062(16) C11 .066(2) .051(2) .0363(19) .010(2) .0099(17) -.0021(18) C12 .070(3) .047(2) .038(2) .005(2) -.0076(18) -.0050(17) C13 .103(3) .084(3) .042(2) .010(3) .028(2) -.003(2) C14 .053(2) .053(2) .047(2) .0159(19) -.0002(18) -.0060(18) C15 .064(3) .044(2) .102(3) -.003(2) .013(3) -.001(2) C16 .096(4) .071(3) .098(3) .030(3) .038(3) -.016(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S .1246 .1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C11 S1 C2 92.27(17) C8 C1 C2 122.8(3) C8 C1 C7 121.6(3) C2 C1 C7 115.5(3) C3 C2 C1 126.5(3) C3 C2 S1 111.1(2) C1 C2 S1 122.4(2) C2 C3 C12 111.0(3) C2 C3 C4 124.3(3) C12 C3 C4 124.6(3) C5 C4 C3 126.4(3) C5 C4 H4 116.8 C3 C4 H4 116.8 C4 C5 C6 126.2(3) C4 C5 H5 116.9 C6 C5 H5 116.9 C7 C6 C5 130.2(3) C7 C6 H6 114.9 C5 C6 H6 114.9 C6 C7 C1 119.0(3) C6 C7 C14 123.8(3) C1 C7 C14 117.0(3) C1 C8 C10 123.2(3) C1 C8 C9 123.2(3) C10 C8 C9 113.6(3) N1 C9 C8 177.1(4) N2 C10 C8 178.1(3) C12 C11 C13 129.7(4) C12 C11 S1 110.9(3) C13 C11 S1 119.4(3) C11 C12 C3 114.7(3) C11 C12 H12 122.7 C3 C12 H12 122.7 C11 C13 H13A 109.5 C11 C13 H13B 109.5 H13A C13 H13B 109.5 C11 C13 H13C 109.5 H13A C13 H13C 109.5 H13B C13 H13C 109.5 C15 C14 C7 109.3(3) C15 C14 C16 110.4(3) C7 C14 C16 114.0(3) C15 C14 H14 107.6 C7 C14 H14 107.6 C16 C14 H14 107.6 C14 C15 H15A 109.5 C14 C15 H15B 109.5 H15A C15 H15B 109.5 C14 C15 H15C 109.5 H15A C15 H15C 109.5 H15B C15 H15C 109.5 C14 C16 H16A 109.5 C14 C16 H16B 109.5 H16A C16 H16B 109.5 C14 C16 H16C 109.5 H16A C16 H16C 109.5 H16B C16 H16C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S1 C11 . 1.719(4) yes S1 C2 . 1.725(3) yes N1 C9 . 1.137(4) yes N2 C10 . 1.133(4) yes C1 C8 . 1.366(4) yes C1 C2 . 1.441(4) yes C1 C7 . 1.480(4) yes C2 C3 . 1.386(4) yes C3 C12 . 1.422(5) yes C3 C4 . 1.442(5) yes C4 C5 . 1.334(5) yes C4 H4 . .930 ? C5 C6 . 1.436(5) yes C5 H5 . .930 ? C6 C7 . 1.350(4) yes C6 H6 . .930 ? C7 C14 . 1.515(5) ? C8 C10 . 1.441(4) yes C8 C9 . 1.441(5) yes C11 C12 . 1.346(5) yes C11 C13 . 1.499(5) ? C12 H12 . .930 ? C13 H13A . .960 ? C13 H13B . .960 ? C13 H13C . .960 ? C14 C15 . 1.512(5) ? C14 C16 . 1.522(5) ? C14 H14 . .980 ? C15 H15A . .960 ? C15 H15B . .960 ? C15 H15C . .960 ? C16 H16A . .960 ? C16 H16B . .960 ? C16 H16C . .960 ? 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 _geom_torsion_publ_flag C8 C1 C2 C3 -129.2(4) ? C7 C1 C2 C3 54.0(4) ? C8 C1 C2 S1 48.9(4) ? C7 C1 C2 S1 -127.8(3) ? C11 S1 C2 C3 .7(3) ? C11 S1 C2 C1 -177.7(3) ? C1 C2 C3 C12 176.2(3) ? S1 C2 C3 C12 -2.1(4) ? C1 C2 C3 C4 -1.1(5) ? S1 C2 C3 C4 -179.4(3) ? C2 C3 C4 C5 -25.1(6) ? C12 C3 C4 C5 158.0(4) ? C3 C4 C5 C6 -5.8(6) ? C4 C5 C6 C7 29.9(6) ? C5 C6 C7 C1 7.8(5) ? C5 C6 C7 C14 -167.9(3) ? C8 C1 C7 C6 125.4(3) ? C2 C1 C7 C6 -57.8(4) ? C8 C1 C7 C14 -58.6(4) ? C2 C1 C7 C14 118.2(3) ? C2 C1 C8 C10 -178.0(3) ? C7 C1 C8 C10 -1.4(5) ? C2 C1 C8 C9 5.0(5) ? C7 C1 C8 C9 -178.4(3) ? C2 S1 C11 C12 1.0(3) ? C2 S1 C11 C13 -178.4(3) ? C13 C11 C12 C3 176.8(4) ? S1 C11 C12 C3 -2.4(4) ? C2 C3 C12 C11 3.0(4) ? C4 C3 C12 C11 -179.7(3) ? C6 C7 C14 C15 112.8(4) ? C1 C7 C14 C15 -63.0(4) yes C6 C7 C14 C16 -11.3(5) ? C1 C7 C14 C16 172.9(3) yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21133018 2 PubChem 101171105