#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/29/2212917.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_2212917
loop_
_publ_author_name
'Ho, Soo Yei'
'Kuan, Fong Sheen'
'Tiekink, Edward R. T.'
_publ_section_title
;
 (E)-O-Methyl N-(4-methylphenyl)thiocarbamate
;
_journal_coeditor_code           HG2200
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1723
_journal_page_last               o1724
_journal_paper_doi               10.1107/S1600536807010914
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C9 H11 N O S'
_chemical_formula_moiety         'C9 H11 N O S'
_chemical_formula_sum            'C9 H11 N O S'
_chemical_formula_weight         181.25
_chemical_name_systematic
;
(E)-O-Methyl N-(4-methylphenyl)thiocarbamate
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                93.590(2)
_cell_angle_beta                 97.398(2)
_cell_angle_gamma                96.247(2)
_cell_formula_units_Z            4
_cell_length_a                   7.4559(7)
_cell_length_b                   11.2260(10)
_cell_length_c                   11.4173(10)
_cell_measurement_reflns_used    2485
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      29.7
_cell_measurement_theta_min      2.5
_cell_volume                     939.19(15)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.023
_diffrn_reflns_av_sigmaI/netI    0.041
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5492
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         1.8
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.296
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.753
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.28
_refine_diff_density_min         -0.39
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.06
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3299
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.06
_refine_ls_R_factor_all          0.057
_refine_ls_R_factor_gt           0.048
_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)+(0.0932P)²+0.1631P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.130
_refine_ls_wR_factor_ref         0.148
_reflns_number_gt                2752
_reflns_number_total             3299
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg2200.cif
_cod_data_source_block           I
_cod_database_code               2212917
_cod_database_fobs_code          2212917
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-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_refinement_flags
_atom_site_occupancy
S S1 0.26074(9) 0.59591(5) 0.49339(5) 0.0416(2) Uani d . 1
S S11 0.27873(9) 0.31283(5) 0.21944(5) 0.0414(2) Uani d . 1
O O1 0.2234(3) 0.46914(15) 0.67877(13) 0.0417(4) Uani d . 1
O O11 0.2998(2) 0.44829(14) 0.03770(13) 0.0363(4) Uani d . 1
N N1 0.2387(3) 0.36156(17) 0.51164(16) 0.0351(5) Uani d . 1
H H1 0.2547 0.3599 0.4374 0.042 Uiso calc R 1
N N11 0.2617(3) 0.54531(17) 0.20650(16) 0.0359(5) Uani d . 1
H H11 0.2477 0.5441 0.2809 0.043 Uiso calc R 1
C C1 0.2396(3) 0.4710(2) 0.56390(19) 0.0333(5) Uani d . 1
C C2 0.2158(3) 0.2471(2) 0.55768(19) 0.0313(5) Uani d . 1
C C3 0.2983(3) 0.1559(2) 0.5057(2) 0.0359(5) Uani d . 1
H H3 0.3688 0.1723 0.4448 0.043 Uiso calc R 1
C C4 0.2774(3) 0.0417(2) 0.5431(2) 0.0401(6) Uani d . 1
H H4 0.3319 -0.0193 0.5058 0.048 Uiso calc R 1
C C5 0.1772(3) 0.0140(2) 0.6351(2) 0.0374(6) Uani d . 1
C C6 0.0942(3) 0.1059(2) 0.6843(2) 0.0414(6) Uani d . 1
H H6 0.0241 0.0895 0.7454 0.050 Uiso calc R 1
C C7 0.1107(3) 0.2209(2) 0.6468(2) 0.0376(6) Uani d . 1
H H7 0.0511 0.2809 0.6813 0.045 Uiso calc R 1
C C8 0.1604(4) -0.1102(2) 0.6774(3) 0.0551(7) Uani d . 1
H H8A 0.2624 -0.1171 0.7375 0.083 Uiso calc R 1
H H8B 0.1604 -0.1688 0.6113 0.083 Uiso calc R 1
H H8C 0.0475 -0.1248 0.7107 0.083 Uiso calc R 1
C C9 0.2071(4) 0.5807(2) 0.7442(2) 0.0490(7) Uani d . 1
H H9A 0.3091 0.6395 0.7356 0.073 Uiso calc R 1
H H9B 0.2071 0.5674 0.8273 0.073 Uiso calc R 1
H H9C 0.0942 0.6104 0.7138 0.073 Uiso calc R 1
C C11 0.2799(3) 0.4394(2) 0.15184(19) 0.0316(5) Uani d . 1
C C12 0.2621(3) 0.6600(2) 0.15947(19) 0.0298(5) Uani d . 1
C C13 0.3628(3) 0.7582(2) 0.2261(2) 0.0385(6) Uani d . 1
H H13 0.4306 0.7477 0.2992 0.046 Uiso calc R 1
C C14 0.3637(3) 0.8709(2) 0.1851(2) 0.0416(6) Uani d . 1
H H14 0.4325 0.9366 0.2311 0.050 Uiso calc R 1
C C15 0.2651(3) 0.8901(2) 0.0770(2) 0.0369(6) Uani d . 1
C C16 0.1641(3) 0.7909(2) 0.0132(2) 0.0362(5) Uani d . 1
H H16 0.0956 0.8010 -0.0599 0.043 Uiso calc R 1
C C17 0.1609(3) 0.6772(2) 0.05358(19) 0.0331(5) Uani d . 1
H H17 0.0895 0.6117 0.0087 0.040 Uiso calc R 1
C C18 0.2662(4) 1.0135(2) 0.0330(3) 0.0551(7) Uani d . 1
H H18A 0.2589 1.0075 -0.0527 0.083 Uiso calc R 1
H H18B 0.3778 1.0627 0.0674 0.083 Uiso calc R 1
H H18C 0.1625 1.0500 0.0559 0.083 Uiso calc R 1
C C19 0.3310(3) 0.3416(2) -0.0311(2) 0.0392(6) Uani d . 1
H H19A 0.4427 0.3132 0.0035 0.059 Uiso calc R 1
H H19B 0.3414 0.3606 -0.1119 0.059 Uiso calc R 1
H H19C 0.2298 0.2795 -0.0311 0.059 Uiso calc R 1
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
_geom_angle_publ_flag
C1 O1 C9 118.36(19) ?
C11 O11 C19 118.26(18) ?
C1 N1 C2 130.31(18) ?
C1 N1 H1 114.8 ?
C2 N1 H1 114.8 ?
C11 N11 C12 128.81(18) ?
C11 N11 H11 115.6 ?
C12 N11 H11 115.6 ?
S1 C1 O1 124.05(17) y
S1 C1 N1 123.44(17) y
O1 C1 N1 112.5(2) y
S11 C11 O11 124.62(17) y
S11 C11 N11 123.21(17) y
O11 C11 N11 112.2(2) y
C7 C2 C3 119.1(2) ?
C7 C2 N1 123.8(2) ?
C3 C2 N1 117.03(19) ?
C4 C3 C2 120.3(2) ?
C4 C3 H3 119.8 ?
C2 C3 H3 119.8 ?
C3 C4 C5 121.7(2) ?
C3 C4 H4 119.2 ?
C5 C4 H4 119.2 ?
C6 C5 C4 116.9(2) ?
C6 C5 C8 122.1(2) ?
C4 C5 C8 121.0(2) ?
C7 C6 C5 122.4(2) ?
C7 C6 H6 118.8 ?
C5 C6 H6 118.8 ?
C6 C7 C2 119.5(2) ?
C6 C7 H7 120.2 ?
C2 C7 H7 120.2 ?
C5 C8 H8A 109.5 ?
C5 C8 H8B 109.5 ?
H8A C8 H8B 109.5 ?
C5 C8 H8C 109.5 ?
H8A C8 H8C 109.5 ?
H8B C8 H8C 109.5 ?
O1 C9 H9A 109.5 ?
O1 C9 H9B 109.5 ?
H9A C9 H9B 109.5 ?
O1 C9 H9C 109.5 ?
H9A C9 H9C 109.5 ?
H9B C9 H9C 109.5 ?
C17 C12 C13 119.2(2) ?
C17 C12 N11 122.5(2) ?
C13 C12 N11 118.2(2) ?
C14 C13 C12 120.1(2) ?
C14 C13 H13 120.0 ?
C12 C13 H13 120.0 ?
C13 C14 C15 121.7(2) ?
C13 C14 H14 119.2 ?
C15 C14 H14 119.2 ?
C16 C15 C14 117.0(2) ?
C16 C15 C18 121.6(2) ?
C14 C15 C18 121.4(2) ?
C17 C16 C15 122.0(2) ?
C17 C16 H16 119.0 ?
C15 C16 H16 119.0 ?
C12 C17 C16 120.0(2) ?
C12 C17 H17 120.0 ?
C16 C17 H17 120.0 ?
C15 C18 H18A 109.5 ?
C15 C18 H18B 109.5 ?
H18A C18 H18B 109.5 ?
C15 C18 H18C 109.5 ?
H18A C18 H18C 109.5 ?
H18B C18 H18C 109.5 ?
O11 C19 H19A 109.5 ?
O11 C19 H19B 109.5 ?
H19A C19 H19B 109.5 ?
O11 C19 H19C 109.5 ?
H19A C19 H19C 109.5 ?
H19B C19 H19C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C1 1.662(2) y
O1 C1 1.334(3) y
N1 C1 1.331(3) y
S11 C11 1.659(2) y
O11 C11 1.339(3) y
N11 C11 1.336(3) y
O1 C9 1.443(3) ?
O11 C19 1.448(3) ?
N1 C2 1.420(3) ?
N1 H1 0.8700 ?
N11 C12 1.425(3) ?
N11 H11 0.8700 ?
C2 C7 1.389(3) ?
C2 C3 1.390(3) ?
C3 C4 1.375(3) ?
C3 H3 0.9400 ?
C4 C5 1.397(3) ?
C4 H4 0.9400 ?
C5 C6 1.385(3) ?
C5 C8 1.501(3) ?
C6 C7 1.383(3) ?
C6 H6 0.9400 ?
C7 H7 0.9400 ?
C8 H8A 0.9700 ?
C8 H8B 0.9700 ?
C8 H8C 0.9700 ?
C9 H9A 0.9700 ?
C9 H9B 0.9700 ?
C9 H9C 0.9700 ?
C12 C17 1.376(3) ?
C12 C13 1.388(3) ?
C13 C14 1.375(3) ?
C13 H13 0.9400 ?
C14 C15 1.395(4) ?
C14 H14 0.9400 ?
C15 C16 1.383(3) ?
C15 C18 1.502(3) ?
C16 C17 1.382(3) ?
C16 H16 0.9400 ?
C17 H17 0.9400 ?
C18 H18A 0.9700 ?
C18 H18B 0.9700 ?
C18 H18C 0.9700 ?
C19 H19A 0.9700 ?
C19 H19B 0.9700 ?
C19 H19C 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
_geom_hbond_publ_flag
N1 H1 S11 1_555 0.87 2.54 3.4032(19) 169 y
N11 H11 S1 1_555 0.87 2.45 3.2902(19) 164 y
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
C2 N1 C1 O1 3.0(3)
C2 N1 C1 S1 -177.58(18)
C9 O1 C1 N1 -174.9(2)
C9 O1 C1 S1 5.7(3)
C1 N1 C2 C7 31.0(4)
C1 N1 C2 C3 -151.8(2)
C7 C2 C3 C4 -0.7(3)
N1 C2 C3 C4 -177.9(2)
C2 C3 C4 C5 -1.4(4)
C3 C4 C5 C6 2.2(4)
C3 C4 C5 C8 -178.1(2)
C4 C5 C6 C7 -1.1(4)
C8 C5 C6 C7 179.3(2)
C5 C6 C7 C2 -0.9(4)
C3 C2 C7 C6 1.8(3)
N1 C2 C7 C6 178.9(2)
C12 N11 C11 O11 -0.3(3)
C12 N11 C11 S11 179.35(17)
C19 O11 C11 N11 176.69(19)
C19 O11 C11 S11 -3.0(3)
C11 N11 C12 C17 47.4(3)
C11 N11 C12 C13 -135.4(2)
C17 C12 C13 C14 -1.2(3)
N11 C12 C13 C14 -178.6(2)
C12 C13 C14 C15 0.0(4)
C13 C14 C15 C16 0.8(4)
C13 C14 C15 C18 179.8(2)
C14 C15 C16 C17 -0.3(3)
C18 C15 C16 C17 -179.3(2)
C13 C12 C17 C16 1.7(3)
N11 C12 C17 C16 178.93(19)
C15 C16 C17 C12 -0.9(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 19506943
