#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/08/2200832.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_2200832 loop_ _publ_author_name 'Jay, David A.' 'Whiting, Andrew' 'Yufit, Dmitrii. S.' 'Howard, Judith A. K.' 'Hermitage, Stephen' _publ_section_title ; p-Tolylsulfonyl cyanide ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o191 _journal_page_last o193 _journal_paper_doi 10.1107/S1600536802001113 _journal_volume 58 _journal_year 2002 _chemical_formula_iupac 'C8 H7 N O2 S' _chemical_formula_moiety 'C8 H7 N O2 S' _chemical_formula_sum 'C8 H7 N O2 S' _chemical_formula_weight 181.21 _chemical_melting_point 321.15 _chemical_name_common 'Tosyl cyanide' _chemical_name_systematic ; p-toluenesulfonyl cyanide ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 93.490(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 6.5810(4) _cell_length_b 15.3770(10) _cell_length_c 8.3671(5) _cell_measurement_reflns_used 1807 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 30.5 _cell_measurement_theta_min 2.8 _cell_volume 845.15(9) _computing_cell_refinement 'SAINT (Bruker, 1997)' _computing_data_collection 'SMART (Bruker, 1997)' _computing_data_reduction SAINT _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Bruker, 1997)' _diffrn_ambient_temperature 120(2) _diffrn_detector_area_resol_mean 8 _diffrn_measured_fraction_theta_full .989 _diffrn_measured_fraction_theta_max .989 _diffrn_measurement_device_type 'Bruker SMART 6000' _diffrn_measurement_method \w _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 .0507 _diffrn_reflns_av_sigmaI/netI .0499 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 6296 _diffrn_reflns_theta_full 30.51 _diffrn_reflns_theta_max 30.51 _diffrn_reflns_theta_min 2.65 _exptl_absorpt_coefficient_mu .337 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.424 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 376 _exptl_crystal_size_max .40 _exptl_crystal_size_mid .18 _exptl_crystal_size_min .10 _refine_diff_density_max .456 _refine_diff_density_min -.366 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref .970 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 137 _refine_ls_number_reflns 2542 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all .970 _refine_ls_R_factor_all .0692 _refine_ls_R_factor_gt .0450 _refine_ls_shift/su_max .001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0750P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt .1184 _refine_ls_wR_factor_ref .1304 _reflns_number_gt 1742 _reflns_number_total 2542 _reflns_threshold_expression I>2\s(I) _cod_data_source_file bt6103.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '48\%C' was changed to '321.15' - it was converted from degrees Celsius(C) to Kelvins(K). 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 '48\%C' was changed to '321.15' - it was converted from degrees Celsius(C) to Kelvins(K). Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2200832 _cod_database_fobs_code 2200832 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol S1 1.18519(7) .60506(3) .35505(5) .03158(16) Uani d . 1 . . S O1 1.0607(2) .53021(8) .32912(17) .0431(4) Uani d . 1 . . O O2 1.3344(2) .62846(10) .24654(17) .0444(4) Uani d . 1 . . O N1 1.4228(3) .57551(11) .6538(2) .0436(4) Uani d . 1 . . N C1 1.0421(3) .69537(11) .4023(2) .0270(4) Uani d . 1 . . C C2 .8574(3) .68434(12) .4720(2) .0328(4) Uani d . 1 . . C C3 .7475(3) .75796(12) .5081(2) .0328(4) Uani d . 1 . . C C4 .8175(3) .84086(11) .4740(2) .0276(4) Uani d . 1 . . C C5 1.0032(3) .84929(11) .4039(2) .0314(4) Uani d . 1 . . C C6 1.1172(3) .77714(11) .3683(2) .0309(4) Uani d . 1 . . C C7 .6962(3) .91988(13) .5144(3) .0350(4) Uani d . 1 . . C C8 1.3263(3) .58573(11) .5387(2) .0312(4) Uani d . 1 . . C H2 .813(3) .6252(14) .495(3) .042(6) Uiso d . 1 . . H H3 .623(4) .7520(15) .554(3) .049(6) Uiso d . 1 . . H H5 1.045(3) .9052(14) .379(3) .040(6) Uiso d . 1 . . H H6 1.251(3) .7850(12) .322(2) .033(5) Uiso d . 1 . . H H71 .730(4) .9669(17) .455(3) .064(8) Uiso d . 1 . . H H72 .550(4) .9084(16) .492(3) .063(8) Uiso d . 1 . . H H73 .730(5) .9373(19) .621(4) .080(9) Uiso d . 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 .0379(3) .0280(2) .0287(2) .00621(17) .00065(19) -.00357(16) O1 .0485(8) .0294(7) .0502(9) .0028(6) -.0068(7) -.0120(6) O2 .0514(8) .0469(8) .0365(8) .0134(7) .0166(7) .0010(6) N1 .0438(10) .0425(10) .0437(10) .0077(8) -.0029(9) .0003(8) C1 .0303(8) .0252(8) .0254(8) .0024(6) .0005(7) .0003(6) C2 .0339(9) .0244(8) .0402(10) -.0019(7) .0030(8) .0018(7) C3 .0300(9) .0294(9) .0398(10) .0001(7) .0079(8) .0026(7) C4 .0327(9) .0252(8) .0246(7) .0044(7) -.0012(7) .0010(6) C5 .0365(9) .0250(9) .0330(9) -.0007(7) .0040(8) .0045(7) C6 .0322(9) .0289(9) .0319(9) .0010(7) .0046(8) .0049(7) C7 .0415(11) .0283(9) .0354(10) .0064(8) .0033(9) -.0002(8) C8 .0331(9) .0247(8) .0358(9) .0046(7) .0038(8) -.0015(7) 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' O O .0106 .0060 '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 _geom_angle_publ_flag O1 S1 O2 121.38(9) y O1 S1 C1 111.51(9) y O2 S1 C1 110.34(8) y O1 S1 C8 105.26(9) y O2 S1 C8 104.50(9) y C1 S1 C8 101.49(8) y C6 C1 C2 121.88(16) y C6 C1 S1 118.26(13) y C2 C1 S1 119.86(13) y C3 C2 C1 118.22(16) y C3 C2 H2 123.5(12) n C1 C2 H2 118.3(12) n C2 C3 C4 121.33(17) y C2 C3 H3 119.6(15) n C4 C3 H3 119.1(15) n C3 C4 C5 118.78(16) y C3 C4 C7 120.52(16) y C5 C4 C7 120.70(16) y C6 C5 C4 121.17(16) y C6 C5 H5 121.7(13) n C4 C5 H5 117.1(13) n C5 C6 C1 118.62(17) y C5 C6 H6 119.5(11) n C1 C6 H6 121.8(11) n C4 C7 H71 111.6(17) n C4 C7 H72 109.8(15) n H71 C7 H72 108(2) n C4 C7 H73 110.0(18) n H71 C7 H73 104(2) n H72 C7 H73 114(2) n N1 C8 S1 177.09(18) y 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 O1 . 1.4217(14) y S1 O2 . 1.4234(14) y S1 C1 . 1.7368(17) y S1 C8 . 1.772(2) y N1 C8 . 1.132(2) y C1 C6 . 1.387(2) y C1 C2 . 1.390(3) y C2 C3 . 1.387(2) y C2 H2 . .98(2) n C3 C4 . 1.391(2) y C3 H3 . .93(2) n C4 C5 . 1.394(2) y C4 C7 . 1.503(2) y C5 C6 . 1.382(2) y C5 H5 . .93(2) n C6 H6 . .993(19) n C7 H71 . .91(3) n C7 H72 . .99(3) n C7 H73 . .95(3) n 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 O1 S1 C1 C6 -154.26(14) O2 S1 C1 C6 -16.26(17) C8 S1 C1 C6 94.10(15) O1 S1 C1 C2 25.57(18) O2 S1 C1 C2 163.56(15) C8 S1 C1 C2 -86.08(16) C6 C1 C2 C3 -.2(3) S1 C1 C2 C3 179.97(14) C1 C2 C3 C4 .9(3) C2 C3 C4 C5 -.8(3) C2 C3 C4 C7 -179.90(18) C3 C4 C5 C6 .1(3) C7 C4 C5 C6 179.15(17) C4 C5 C6 C1 .6(3) C2 C1 C6 C5 -.5(3) S1 C1 C6 C5 179.32(14) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 79343 2 PubChem 87946