#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/43/2204332.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_2204332 loop_ _publ_author_name 'Homrighausen, Craig L.' 'Krause Bauer, Jeanette A.' _publ_section_title ; 2-(4-Chlorophenyl)-4,4-bis(methylsulfanyl)-1,3-butadiene-1,1-dicarbonitrile ; _journal_issue 10 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1828 _journal_page_last o1829 _journal_paper_doi 10.1107/S1600536804022986 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C14 H11 Cl N2 S2' _chemical_formula_moiety 'C14 H11 Cl N2 S2' _chemical_formula_sum 'C14 H11 Cl N2 S2' _chemical_formula_weight 306.82 _chemical_name_systematic ; 2-(4-Chlorophenyl)-4,4-bis(methylsulfanyl)-1,3-butadiene-1,1-dicarbonitrile ; _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' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method 'SHELXTL v5.03' _cell_angle_alpha 90.00 _cell_angle_beta 98.40(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 9.1633(18) _cell_length_b 11.836(2) _cell_length_c 13.911(3) _cell_measurement_reflns_used 40 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 15.0 _cell_measurement_theta_min 5.0 _cell_volume 1492.6(5) _computing_cell_refinement P3/P4-PC _computing_data_collection 'P3/P4-PC (Siemens, 1989)' _computing_data_reduction 'XDISK (Siemens, 1989)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 2000)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Siemens P3' _diffrn_measurement_method \q--2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.024 _diffrn_reflns_av_sigmaI/netI 0.037 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 3649 _diffrn_reflns_theta_full 27.55 _diffrn_reflns_theta_max 27.6 _diffrn_reflns_theta_min 2.3 _diffrn_standards_decay_% <2 _diffrn_standards_interval_count 300 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.52 _exptl_absorpt_correction_type none _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.365 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 632 _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.40 _refine_diff_density_max 0.37 _refine_diff_density_min -0.33 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.01 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 172 _refine_ls_number_reflns 3442 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.01 _refine_ls_R_factor_all 0.078 _refine_ls_R_factor_gt 0.043 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0365P)^2^+0.6836P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.088 _refine_ls_wR_factor_ref 0.102 _reflns_number_gt 2345 _reflns_number_total 3442 _reflns_threshold_expression I>2\s(I) _cod_data_source_file er6001.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2204332 _cod_database_fobs_code 2204332 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_ _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_type_symbol Cl1 0.26745(10) 0.97560(7) 0.49461(5) 0.0814(3) Uani d . 1 Cl S1 0.12018(8) 0.87710(6) 0.10780(5) 0.05283(18) Uani d . 1 S S2 0.14420(9) 0.84396(6) -0.09845(5) 0.0594(2) Uani d . 1 S N1 0.5335(3) 1.3189(2) 0.19990(17) 0.0707(7) Uani d . 1 N N2 0.4318(3) 1.2400(2) -0.10914(17) 0.0644(6) Uani d . 1 N C1 0.2917(3) 1.0080(2) 0.37617(16) 0.0487(6) Uani d . 1 C C2 0.2142(3) 1.0966(2) 0.33022(18) 0.0512(6) Uani d . 1 C H2 0.1490 1.1380 0.3617 0.061 Uiso calc R 1 H C3 0.2345(3) 1.12338(19) 0.23643(17) 0.0456(5) Uani d . 1 C H3 0.1849 1.1849 0.2054 0.055 Uiso calc R 1 H C4 0.3274(2) 1.05992(17) 0.18836(15) 0.0379(5) Uani d . 1 C C5 0.4049(3) 0.97193(19) 0.23698(17) 0.0459(5) Uani d . 1 C H5 0.4690 0.9293 0.2055 0.055 Uiso calc R 1 H C6 0.3886(3) 0.9464(2) 0.33146(17) 0.0501(6) Uani d . 1 C H6 0.4428 0.8880 0.3643 0.060 Uiso calc R 1 H C7 0.3433(2) 1.08571(18) 0.08595(15) 0.0393(5) Uani d . 1 C C8 0.4130(3) 1.18447(18) 0.06690(16) 0.0424(5) Uani d . 1 C C9 0.2899(3) 1.01202(19) 0.00832(15) 0.0432(5) Uani d . 1 C H9 0.3235 1.0272 -0.0503 0.052 Uiso calc R 1 H C10 0.4782(3) 1.2594(2) 0.14157(18) 0.0496(6) Uani d . 1 C C11 0.4253(3) 1.2169(2) -0.03036(19) 0.0483(6) Uani d . 1 C C12 0.1962(3) 0.92205(19) 0.00705(16) 0.0424(5) Uani d . 1 C C13 -0.0076(3) 0.7681(2) 0.06349(19) 0.0587(7) Uani d . 1 C H13A -0.0539 0.7393 0.1161 0.088 Uiso calc R 1 H H13B 0.0440 0.7081 0.0365 0.088 Uiso calc R 1 H H13C -0.0814 0.7985 0.0142 0.088 Uiso calc R 1 H C14 0.2045(3) 0.9234(2) -0.19412(17) 0.0651(8) Uani d . 1 C H14A 0.1785 0.8840 -0.2545 0.098 Uiso calc R 1 H H14B 0.3096 0.9327 -0.1812 0.098 Uiso calc R 1 H H14C 0.1579 0.9962 -0.1982 0.098 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 Cl1 0.1117(7) 0.0860(6) 0.0491(4) -0.0068(5) 0.0209(4) 0.0102(4) S1 0.0604(4) 0.0474(4) 0.0501(3) -0.0151(3) 0.0060(3) -0.0019(3) S2 0.0747(5) 0.0505(4) 0.0509(4) -0.0133(3) 0.0018(3) -0.0121(3) N1 0.0828(18) 0.0620(15) 0.0673(15) -0.0199(13) 0.0108(13) -0.0181(12) N2 0.0828(17) 0.0560(14) 0.0575(13) -0.0052(12) 0.0202(12) 0.0066(11) C1 0.0574(15) 0.0473(14) 0.0407(12) -0.0113(12) 0.0045(11) 0.0020(10) C2 0.0516(15) 0.0512(15) 0.0528(14) 0.0030(12) 0.0141(12) -0.0058(12) C3 0.0476(13) 0.0373(12) 0.0512(13) 0.0050(11) 0.0053(11) 0.0015(10) C4 0.0391(12) 0.0317(11) 0.0416(11) -0.0026(9) 0.0017(9) -0.0015(9) C5 0.0488(14) 0.0404(13) 0.0475(12) 0.0066(11) 0.0041(10) -0.0022(10) C6 0.0587(15) 0.0387(13) 0.0497(13) 0.0044(12) -0.0030(11) 0.0049(11) C7 0.0402(12) 0.0352(11) 0.0418(11) 0.0003(10) 0.0040(9) 0.0001(9) C8 0.0459(13) 0.0372(12) 0.0442(12) -0.0004(10) 0.0070(10) -0.0010(10) C9 0.0510(14) 0.0407(12) 0.0382(11) -0.0012(11) 0.0071(10) -0.0014(9) C10 0.0532(15) 0.0423(13) 0.0547(14) -0.0057(11) 0.0125(12) -0.0023(11) C11 0.0530(15) 0.0375(12) 0.0555(14) -0.0041(11) 0.0124(12) -0.0011(11) C12 0.0450(13) 0.0366(12) 0.0438(12) 0.0031(10) 0.0004(10) -0.0012(10) C13 0.0550(16) 0.0508(15) 0.0674(16) -0.0145(13) -0.0013(13) 0.0024(13) C14 0.081(2) 0.0671(18) 0.0444(14) -0.0038(16) 0.0010(13) -0.0087(13) 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' Cl Cl 0.1484 0.1585 '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 _geom_angle_publ_flag C12 S1 C13 105.20(12) ? C12 S2 C14 105.84(12) ? C6 C1 C2 121.5(2) ? C6 C1 Cl1 119.65(19) ? C2 C1 Cl1 118.8(2) ? C1 C2 C3 118.9(2) ? C1 C2 H2 120.5 ? C3 C2 H2 120.5 ? C4 C3 C2 120.7(2) ? C4 C3 H3 119.6 ? C2 C3 H3 119.6 ? C3 C4 C5 118.9(2) ? C3 C4 C7 120.5(2) ? C5 C4 C7 120.6(2) ? C6 C5 C4 120.9(2) ? C6 C5 H5 119.6 ? C4 C5 H5 119.6 ? C1 C6 C5 119.0(2) ? C1 C6 H6 120.5 ? C5 C6 H6 120.5 ? C8 C7 C9 119.6(2) ? C8 C7 C4 118.21(19) ? C9 C7 C4 122.19(19) ? C7 C8 C11 121.0(2) ? C7 C8 C10 122.9(2) ? C11 C8 C10 116.1(2) ? C12 C9 C7 129.5(2) ? C12 C9 H9 115.3 ? C7 C9 H9 115.3 ? N1 C10 C8 178.1(3) y N2 C11 C8 177.7(3) y C9 C12 S1 123.60(18) ? C9 C12 S2 121.26(18) ? S1 C12 S2 115.13(13) ? S1 C13 H13A 109.5 ? S1 C13 H13B 109.5 ? H13A C13 H13B 109.5 ? S1 C13 H13C 109.5 ? H13A C13 H13C 109.5 ? H13B C13 H13C 109.5 ? S2 C14 H14A 109.5 ? S2 C14 H14B 109.5 ? H14A C14 H14B 109.5 ? S2 C14 H14C 109.5 ? H14A C14 H14C 109.5 ? H14B C14 H14C 109.5 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Cl1 C1 1.737(2) ? S1 C12 1.737(2) y S1 C13 1.790(3) y S2 C12 1.741(2) ? S2 C14 1.782(3) ? N1 C10 1.136(3) y N2 C11 1.140(3) y C1 C6 1.368(3) ? C1 C2 1.371(3) ? C2 C3 1.381(3) ? C2 H2 0.9300 ? C3 C4 1.380(3) ? C3 H3 0.9300 ? C4 C5 1.381(3) ? C4 C7 1.485(3) y C5 C6 1.378(3) ? C5 H5 0.9300 ? C6 H6 0.9300 ? C7 C8 1.376(3) y C7 C9 1.419(3) y C8 C11 1.427(3) y C8 C10 1.429(3) y C9 C12 1.366(3) y C9 H9 0.9300 ? C13 H13A 0.9600 ? C13 H13B 0.9600 ? C13 H13C 0.9600 ? C14 H14A 0.9600 ? C14 H14B 0.9600 ? C14 H14C 0.9600 ? 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 C6 C1 C2 C3 0.3(4) ? Cl1 C1 C2 C3 0.72(18) ? C1 C2 C3 C4 2.1(4) ? C2 C3 C4 C5 2.7(3) ? C2 C3 C4 C7 2.9(2) ? C3 C4 C5 C6 0.9(3) ? C7 C4 C5 C6 1.1(2) ? C2 C1 C6 C5 2.1(4) ? Cl1 C1 C6 C5 1.03(18) ? C4 C5 C6 C1 1.4(4) ? C3 C4 C7 C8 69.0(3) ? C5 C4 C7 C8 68.8(2) ? C3 C4 C7 C9 68.7(3) ? C5 C4 C7 C9 68.5(3) ? C9 C7 C8 C11 3.4(3) ? C4 C7 C8 C11 3.1(2) ? C9 C7 C8 C10 4.2(2) y C4 C7 C8 C10 3.9(3) ? C8 C7 C9 C12 13.0(2) y C4 C7 C9 C12 13.3(4) ? C7 C8 C10 N1 53(9) ? C7 C8 C11 N2 13(7) ? C7 C9 C12 S1 0.4(4) y C7 C9 C12 S2 0.65(19) ? C13 S1 C12 C9 6.1(2) ? C13 S1 C12 S2 5.88(17) ? C14 S2 C12 C9 11.5(2) ? C14 S2 C12 S1 11.69(14) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 2006741 2 PubChem 2724614