#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/07/2240753.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_2240753
loop_
_publ_author_name
'Bano, Huma'
'Yousuf, Sammer'
_publ_section_title
;
 Crystal structure of p-toluenesulfonylmethyl isocyanide
;
_journal_coeditor_code           RZ5158
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o412
_journal_paper_doi               10.1107/S2056989015008816
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C9 H9 N O2 S'
_chemical_formula_moiety         'C9 H9 N O2 S'
_chemical_formula_sum            'C9 H9 N O2 S'
_chemical_formula_weight         195.23
_chemical_name_systematic
;
p-Toluenesulfonylmethyl isocyanide
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.342(5)
_cell_length_b                   8.881(2)
_cell_length_c                   4.8462(12)
_cell_measurement_reflns_used    830
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      22.26
_cell_measurement_theta_min      2.93
_cell_volume                     961.6(4)
_computing_cell_refinement
;
SAINT (Bruker, 2000)
;
_computing_data_collection
;
SMART (Bruker, 2000)
;
_computing_data_reduction
;
SAINT (Bruker, 2000)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON
(Spek, 2009)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type
;
Bruker SMART APEX CCD area-detector
;
_diffrn_measurement_method       'ω scan'
_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  0.0441
_diffrn_reflns_av_sigmaI/netI    0.0317
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            5160
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         1.82
_exptl_absorpt_coefficient_mu    0.302
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_correction_T_min  0.864
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2000)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.188
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     77
_refine_ls_number_reflns         955
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.113
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0471
_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/[σ²(Fo²)+(0.0557P)²+0.1844P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1092
_refine_ls_wR_factor_ref         0.1188
_reflns_number_gt                733
_reflns_number_total             955
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz5158sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P n m a '
_cod_database_code               2240753
_cod_database_fobs_code          2240753
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'
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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
S S1 0.28836(4) 0.2500 0.85946(16) 0.0354(3) Uani d S 1 2
O O1 0.28301(8) 0.11111(18) 1.0084(3) 0.0462(5) Uani d . 1 1
N N1 0.17475(16) 0.2500 0.7198(6) 0.0483(8) Uani d S 1 2
C C1 0.35416(16) 0.2500 0.6642(7) 0.0379(9) Uani d S 1 2
C C2 0.37872(13) 0.1154(3) 0.5815(6) 0.0488(7) Uani d . 1 1
H H2A 0.3624 0.0246 0.6398 0.059 Uiso calc R 1 1
C C3 0.42793(13) 0.1177(3) 0.4109(6) 0.0557(8) Uani d . 1 1
H H3A 0.4446 0.0268 0.3543 0.067 Uiso calc R 1 1
C C4 0.45334(18) 0.2500 0.3212(7) 0.0477(10) Uani d S 1 2
C C5 0.5064(2) 0.2500 0.1335(11) 0.0714(16) Uani d SD 1 2
H H5B 0.505(2) 0.320(5) 0.013(11) 0.14(2) Uiso d . 1 1
C C6 0.23235(16) 0.2500 0.5941(7) 0.0383(9) Uani d S 1 2
H H6A 0.2369 0.3385 0.4788 0.046 Uiso calc PR 0.50 1
H H6B 0.2369 0.1615 0.4788 0.046 Uiso calc PR 0.50 1
C C7 0.1292(2) 0.2500 0.8320(11) 0.0707(14) Uani d S 1 2
H H5A 0.549(2) 0.2500 0.242(17) 0.21(4) Uiso d SD 1 2
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'
O O 0.0106 0.0060 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
O1 S1 O1 7_565 . 118.66(14)
O1 S1 C1 7_565 . 110.03(9)
O1 S1 C1 . . 110.03(9)
O1 S1 C6 7_565 . 107.61(10)
O1 S1 C6 . . 107.61(10)
C1 S1 C6 . . 101.45(16)
C7 N1 C6 . . 177.2(4)
C2 C1 C2 7_565 . 120.8(3)
C2 C1 S1 7_565 . 119.56(18)
C2 C1 S1 . . 119.56(18)
C1 C2 C3 . . 118.8(3)
C1 C2 H2A . . 120.6
C3 C2 H2A . . 120.6
C4 C3 C2 . . 122.2(3)
C4 C3 H3A . . 118.9
C2 C3 H3A . . 118.9
C3 C4 C3 . 7_565 117.3(4)
C3 C4 C5 . . 121.33(18)
C3 C4 C5 7_565 . 121.33(18)
C4 C5 H5B . . 113(3)
C4 C5 H5A . . 114(5)
H5B C5 H5A . . 111(4)
N1 C6 S1 . . 108.9(2)
N1 C6 H6A . . 109.9
S1 C6 H6A . . 109.9
N1 C6 H6B . . 109.9
S1 C6 H6B . . 109.9
H6A C6 H6B . . 108.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
S1 O1 7_565 1.4340(16)
S1 O1 . 1.4341(16)
S1 C1 . 1.748(4)
S1 C6 . 1.794(4)
N1 C7 . 1.154(5)
N1 C6 . 1.424(5)
C1 C2 7_565 1.375(3)
C1 C2 . 1.375(3)
C2 C3 . 1.376(4)
C2 H2A . 0.9300
C3 C4 . 1.375(4)
C3 H3A . 0.9300
C4 C3 7_565 1.375(4)
C4 C5 . 1.494(6)
C5 H5B . 0.85(5)
C5 H5A . 1.095(10)
C6 H6A . 0.9700
C6 H6B . 0.9700
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
C6 H6A O1 8_665 0.97 2.47 3.2519(18) 138.0
C6 H6A O1 7_564 0.97 2.54 3.296(4) 134.6
C6 H6B O1 1_554 0.97 2.54 3.296(4) 134.6
C6 H6B O1 2_554 0.97 2.47 3.2519(18) 138.0
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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
O1 S1 C1 C2 7_565 7_565 -25.6(3)
O1 S1 C1 C2 . 7_565 -158.2(2)
C6 S1 C1 C2 . 7_565 88.1(3)
O1 S1 C1 C2 7_565 . 158.2(2)
O1 S1 C1 C2 . . 25.6(3)
C6 S1 C1 C2 . . -88.1(3)
C2 C1 C2 C3 7_565 . -0.9(6)
S1 C1 C2 C3 . . 175.2(2)
C1 C2 C3 C4 . . 0.2(5)
C2 C3 C4 C3 . 7_565 0.6(6)
C2 C3 C4 C5 . . -179.3(4)
O1 S1 C6 N1 7_565 . -64.47(9)
O1 S1 C6 N1 . . 64.47(9)
C1 S1 C6 N1 . . 180.0
