#------------------------------------------------------------------------------ #$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $ #$Revision: 201974 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/21/51/2215126.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_2215126 loop_ _publ_author_name 'Venkatesha R. Hathwar' 'P. Manivel' 'Nawaz Khan, F.' 'Guru Row, T. N.' _publ_section_title ; 3-Butyl-1H-isochromene-1-thione ; _journal_coeditor_code HB2499 _journal_issue 9 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o3708 _journal_page_last o3708 _journal_paper_doi 10.1107/S1600536807037683 _journal_volume 63 _journal_year 2007 _chemical_formula_iupac 'C13 H14 O S' _chemical_formula_moiety 'C13 H14 O S' _chemical_formula_structural 'C13 H14 O S' _chemical_formula_sum 'C13 H14 O S' _chemical_formula_weight 218.31 _chemical_name_systematic ; 3-Butyl-1H-isochromene-1-thione ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 82.0320(10) _cell_angle_beta 76.7130(10) _cell_angle_gamma 62.9240(10) _cell_formula_units_Z 2 _cell_length_a 7.8699(6) _cell_length_b 8.5840(6) _cell_length_c 9.8083(7) _cell_measurement_reflns_used 2281 _cell_measurement_temperature 290(2) _cell_measurement_theta_max 25.34 _cell_measurement_theta_min 2.67 _cell_volume 573.75(7) _computing_cell_refinement 'SAINT (Bruker, 2004)' _computing_data_collection 'SMART (Bruker, 2004)' _computing_data_reduction SAINT _computing_molecular_graphics ; ORTEP-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993) ; _computing_publication_material 'PLATON (Spek, 2003)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _diffrn_ambient_temperature 290(2) _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method \w _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 0.0144 _diffrn_reflns_av_sigmaI/netI 0.0175 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 6031 _diffrn_reflns_reduction_process ; ; _diffrn_reflns_theta_full 26.00 _diffrn_reflns_theta_max 26.00 _diffrn_reflns_theta_min 2.14 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.252 _exptl_absorpt_correction_T_max 0.9875 _exptl_absorpt_correction_T_min 0.9381 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.264 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 232 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.172 _refine_diff_density_min -0.210 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 192 _refine_ls_number_reflns 2249 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.051 _refine_ls_R_factor_all 0.0535 _refine_ls_R_factor_gt 0.0409 _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^)+(0.0594P)^2^+0.0575P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0998 _refine_ls_wR_factor_ref 0.1068 _reflns_number_gt 1777 _reflns_number_total 2249 _reflns_threshold_expression I>2\s(I) _cod_data_source_file hb2499.cif _cod_data_source_block I _cod_database_code 2215126 _cod_database_fobs_code 2215126 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,-z 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_occupancy S S1 0.43615(8) 0.25638(6) -0.32536(5) 0.0693(2) Uani d 1 O O1 0.30654(16) 0.27779(13) -0.06157(11) 0.0519(3) Uani d 1 C C1 0.3570(2) 0.3626(2) -0.17997(17) 0.0487(4) Uani d 1 C C2 0.3340(2) 0.53771(19) -0.16539(16) 0.0473(4) Uani d 1 C C3 0.3829(3) 0.6351(2) -0.28165(19) 0.0558(4) Uani d 1 C C4 0.3587(3) 0.8002(2) -0.2656(2) 0.0618(5) Uani d 1 C C5 0.2869(3) 0.8736(2) -0.1350(2) 0.0632(5) Uani d 1 C C6 0.2392(3) 0.7808(2) -0.0203(2) 0.0582(4) Uani d 1 C C7 0.2605(2) 0.6114(2) -0.03317(17) 0.0490(4) Uani d 1 C C8 0.2109(3) 0.5103(2) 0.08443(19) 0.0522(4) Uani d 1 C C9 0.2350(2) 0.3500(2) 0.06889(17) 0.0485(4) Uani d 1 C C10 0.1948(3) 0.2248(2) 0.17760(18) 0.0530(4) Uani d 1 C C11 0.1120(3) 0.2967(2) 0.32359(18) 0.0515(4) Uani d 1 C C12 0.0685(3) 0.1694(2) 0.43241(19) 0.0588(5) Uani d 1 C C13 -0.0232(4) 0.2464(3) 0.5754(2) 0.0713(6) Uani d 1 H H3 0.429(3) 0.585(3) -0.368(2) 0.066(5) Uiso d 1 H H4 0.395(3) 0.857(3) -0.341(2) 0.067(6) Uiso d 1 H H5 0.274(3) 0.990(3) -0.127(2) 0.074(6) Uiso d 1 H H6 0.196(3) 0.824(3) 0.065(2) 0.068(6) Uiso d 1 H H8 0.165(3) 0.557(2) 0.170(2) 0.063(5) Uiso d 1 H H10A 0.316(3) 0.124(2) 0.1765(17) 0.055(5) Uiso d 1 H H10B 0.106(3) 0.193(2) 0.1454(19) 0.066(5) Uiso d 1 H H11A 0.201(2) 0.328(2) 0.3513(17) 0.052(4) Uiso d 1 H H11B -0.010(3) 0.403(3) 0.3205(19) 0.063(5) Uiso d 1 H H12A 0.189(3) 0.066(3) 0.438(2) 0.069(5) Uiso d 1 H H12B -0.015(3) 0.136(3) 0.397(2) 0.081(6) Uiso d 1 H H13A 0.054(3) 0.288(3) 0.611(2) 0.095(7) Uiso d 1 H H13B -0.139(4) 0.348(3) 0.566(3) 0.099(8) Uiso d 1 H H13C -0.053(3) 0.171(3) 0.645(3) 0.100(8) Uiso d 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 0.0912(4) 0.0545(3) 0.0547(3) -0.0277(3) -0.0019(2) -0.0138(2) O1 0.0646(7) 0.0413(6) 0.0495(6) -0.0236(5) -0.0082(5) -0.0040(5) C1 0.0479(9) 0.0433(8) 0.0517(9) -0.0163(7) -0.0117(7) -0.0012(7) C2 0.0477(8) 0.0418(8) 0.0514(9) -0.0176(7) -0.0136(7) 0.0007(7) C3 0.0620(10) 0.0541(10) 0.0501(10) -0.0251(8) -0.0116(8) 0.0024(8) C4 0.0695(12) 0.0543(10) 0.0646(12) -0.0320(9) -0.0169(9) 0.0135(9) C5 0.0739(12) 0.0456(9) 0.0746(13) -0.0297(9) -0.0166(10) 0.0003(9) C6 0.0725(12) 0.0439(9) 0.0599(11) -0.0270(8) -0.0103(9) -0.0055(8) C7 0.0521(9) 0.0416(8) 0.0529(9) -0.0192(7) -0.0124(7) -0.0016(7) C8 0.0639(10) 0.0459(9) 0.0478(9) -0.0257(8) -0.0079(8) -0.0040(7) C9 0.0529(9) 0.0439(8) 0.0484(9) -0.0205(7) -0.0096(7) -0.0037(7) C10 0.0611(11) 0.0424(9) 0.0574(10) -0.0253(8) -0.0100(8) -0.0007(7) C11 0.0562(10) 0.0446(9) 0.0566(10) -0.0257(8) -0.0084(8) -0.0017(7) C12 0.0722(12) 0.0466(10) 0.0577(11) -0.0296(9) -0.0046(9) -0.0027(8) C13 0.0934(16) 0.0656(13) 0.0614(12) -0.0470(13) 0.0032(11) -0.0091(10) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 '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' C C 0.0033 0.0016 '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 C1 O1 C9 123.44(12) O1 C1 C2 117.11(14) O1 C1 S1 116.27(11) C2 C1 S1 126.61(13) C7 C2 C3 119.31(15) C7 C2 C1 119.49(14) C3 C2 C1 121.20(15) C4 C3 C2 120.19(18) C4 C3 H3 121.6(13) C2 C3 H3 118.2(13) C3 C4 C5 120.79(18) C3 C4 H4 117.8(13) C5 C4 H4 121.3(13) C6 C5 C4 120.01(17) C6 C5 H5 121.2(12) C4 C5 H5 118.8(12) C5 C6 C7 120.73(18) C5 C6 H6 121.3(14) C7 C6 H6 118.0(14) C2 C7 C6 118.97(15) C2 C7 C8 118.61(14) C6 C7 C8 122.42(16) C9 C8 C7 120.86(16) C9 C8 H8 120.5(12) C7 C8 H8 118.6(12) C8 C9 O1 120.49(15) C8 C9 C10 128.69(15) O1 C9 C10 110.82(13) C9 C10 C11 113.79(14) C9 C10 H10A 105.7(10) C11 C10 H10A 110.4(10) C9 C10 H10B 106.5(11) C11 C10 H10B 111.4(11) H10A C10 H10B 108.7(15) C12 C11 C10 113.22(14) C12 C11 H11A 109.4(10) C10 C11 H11A 109.4(10) C12 C11 H11B 107.9(11) C10 C11 H11B 108.4(11) H11A C11 H11B 108.4(15) C13 C12 C11 112.48(16) C13 C12 H12A 109.5(11) C11 C12 H12A 108.4(12) C13 C12 H12B 112.2(12) C11 C12 H12B 106.3(13) H12A C12 H12B 107.7(17) C12 C13 H13A 113.6(14) C12 C13 H13B 107.5(15) H13A C13 H13B 104(2) C12 C13 H13C 114.5(15) H13A C13 H13C 108(2) H13B C13 H13C 109(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 C1 1.6396(16) O1 C1 1.361(2) O1 C9 1.3817(19) C1 C2 1.453(2) C2 C7 1.402(2) C2 C3 1.405(2) C3 C4 1.368(3) C3 H3 0.92(2) C4 C5 1.387(3) C4 H4 0.89(2) C5 C6 1.368(3) C5 H5 0.97(2) C6 C7 1.407(2) C6 H6 0.89(2) C7 C8 1.436(2) C8 C9 1.326(2) C8 H8 0.904(19) C9 C10 1.493(2) C10 C11 1.518(2) C10 H10A 0.950(17) C10 H10B 0.98(2) C11 C12 1.516(2) C11 H11A 0.954(18) C11 H11B 0.985(19) C12 C13 1.510(3) C12 H12A 0.97(2) C12 H12B 0.97(2) C13 H13A 0.97(2) C13 H13B 0.95(3) C13 H13C 0.94(3) 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 C3 H3 S1 . 0.92(2) 2.77(2) 3.1621(18) 106.7(16) yes C10 H10B Cg 2_565 0.98(2) 2.98(2) 3.813(3) 144.1(13) yes 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 C9 O1 C1 C2 0.4(2) C9 O1 C1 S1 -179.15(11) O1 C1 C2 C7 -0.6(2) S1 C1 C2 C7 178.82(12) O1 C1 C2 C3 179.74(14) S1 C1 C2 C3 -0.8(2) C7 C2 C3 C4 -0.1(3) C1 C2 C3 C4 179.51(16) C2 C3 C4 C5 0.4(3) C3 C4 C5 C6 -0.1(3) C4 C5 C6 C7 -0.5(3) C3 C2 C7 C6 -0.4(2) C1 C2 C7 C6 179.91(15) C3 C2 C7 C8 179.89(14) C1 C2 C7 C8 0.2(2) C5 C6 C7 C2 0.8(3) C5 C6 C7 C8 -179.58(17) C2 C7 C8 C9 0.5(2) C6 C7 C8 C9 -179.20(16) C7 C8 C9 O1 -0.8(3) C7 C8 C9 C10 179.12(16) C1 O1 C9 C8 0.3(2) C1 O1 C9 C10 -179.55(14) C8 C9 C10 C11 1.2(3) O1 C9 C10 C11 -178.92(14) C9 C10 C11 C12 178.94(16) C10 C11 C12 C13 -177.06(19) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21123609