#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:03:29 +0200 (vie 13 de oct de 2017) $
#$Revision: 201974 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/27/2212756.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_2212756
loop_
_publ_author_name
'Primjira P. Tadbuppa'
'Tiekink, Edward R. T.'
_publ_section_title
;
 (E)-O-Ethyl N-(4-chlorophenyl)thiocarbamate
;
_journal_coeditor_code           AT2237
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1779
_journal_page_last               o1780
_journal_paper_doi               10.1107/S1600536807011312
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C9 H10 Cl N O S'
_chemical_formula_moiety         'C9 H10 Cl N O S'
_chemical_formula_sum            'C9 H10 Cl N O S'
_chemical_formula_weight         215.69
_chemical_name_systematic
;
(E)-O-Ethyl N-(4-chlorophenyl)thiocarbamate
;
_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           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 96.402(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7544(12)
_cell_length_b                   4.5159(6)
_cell_length_c                   25.794(4)
_cell_measurement_reflns_used    1000
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      29.0
_cell_measurement_theta_min      2.4
_cell_volume                     1013.4(2)
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'φ and ω'
_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  0.033
_diffrn_reflns_av_sigmaI/netI    0.039
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            7899
_diffrn_reflns_theta_full        30.0
_diffrn_reflns_theta_max         30.0
_diffrn_reflns_theta_min         1.6
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.542
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.718
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.44
_refine_diff_density_min         -0.24
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.15
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         2952
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.15
_refine_ls_R_factor_all          0.074
_refine_ls_R_factor_gt           0.061
_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/[σ²(Fo²)+(0.0643P)²+0.3778P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.146
_refine_ls_wR_factor_ref         0.153
_reflns_number_gt                2483
_reflns_number_total             2952
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2237.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2212756
_cod_database_fobs_code          2212756
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_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
Cl Cl1 0.43225(9) 0.28880(17) 0.72729(2) 0.0559(2) Uani d . 1
S S1 0.71978(7) 1.20673(16) 1.00950(2) 0.0436(2) Uani d . 1
O O1 0.82425(17) 1.1026(4) 0.91852(6) 0.0365(4) Uani d . 1
N N1 0.6082(2) 0.8681(4) 0.93103(7) 0.0336(4) Uani d . 1
H H1 0.5422 0.8236 0.9526 0.040 Uiso calc R 1
C C1 0.7183(2) 1.0553(5) 0.95051(8) 0.0314(4) Uani d . 1
C C2 0.5793(2) 0.7286(5) 0.88171(8) 0.0313(4) Uani d . 1
C C3 0.4602(2) 0.5227(5) 0.87690(9) 0.0357(5) Uani d . 1
H H3 0.4099 0.4758 0.9062 0.043 Uiso calc R 1
C C4 0.4149(3) 0.3868(6) 0.82993(9) 0.0404(5) Uani d . 1
H H4 0.3337 0.2495 0.8270 0.048 Uiso calc R 1
C C5 0.4906(3) 0.4549(5) 0.78710(8) 0.0371(5) Uani d . 1
C C6 0.6108(3) 0.6508(6) 0.79135(9) 0.0420(5) Uani d . 1
H H6 0.6625 0.6914 0.7621 0.050 Uiso calc R 1
C C7 0.6567(3) 0.7896(6) 0.83845(9) 0.0416(5) Uani d . 1
H H7 0.7393 0.9238 0.8412 0.050 Uiso calc R 1
C C8 0.9476(3) 1.3132(6) 0.93333(9) 0.0391(5) Uani d . 1
H H8A 1.0133 1.2430 0.9641 0.047 Uiso calc R 1
H H8B 0.9054 1.5070 0.9412 0.047 Uiso calc R 1
C C9 1.0371(3) 1.3339(8) 0.88729(11) 0.0568(8) Uani d . 1
H H9A 1.1214 1.4720 0.8949 0.085 Uiso calc R 1
H H9B 0.9702 1.4027 0.8572 0.085 Uiso calc R 1
H H9C 1.0775 1.1402 0.8800 0.085 Uiso calc R 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
Cl1 0.0685(5) 0.0637(4) 0.0344(3) -0.0048(3) 0.0011(3) -0.0141(3)
S1 0.0397(3) 0.0585(4) 0.0341(3) -0.0095(3) 0.0102(2) -0.0134(3)
O1 0.0336(8) 0.0438(9) 0.0333(8) -0.0076(7) 0.0099(6) -0.0063(7)
N1 0.0355(9) 0.0397(10) 0.0270(8) -0.0074(7) 0.0089(7) -0.0027(7)
C1 0.0300(9) 0.0347(11) 0.0299(10) 0.0021(8) 0.0051(7) 0.0006(8)
C2 0.0331(10) 0.0326(10) 0.0287(10) 0.0025(8) 0.0055(8) 0.0002(8)
C3 0.0343(10) 0.0401(12) 0.0341(11) -0.0013(9) 0.0106(8) -0.0028(9)
C4 0.0358(11) 0.0455(13) 0.0400(12) -0.0065(10) 0.0049(9) -0.0072(10)
C5 0.0427(11) 0.0402(12) 0.0280(10) 0.0056(9) 0.0020(8) -0.0032(9)
C6 0.0500(13) 0.0489(14) 0.0289(11) -0.0040(11) 0.0124(9) 0.0000(10)
C7 0.0461(13) 0.0469(13) 0.0333(11) -0.0119(10) 0.0112(9) -0.0004(10)
C8 0.0330(11) 0.0440(12) 0.0410(12) -0.0080(9) 0.0069(9) -0.0063(10)
C9 0.0513(15) 0.078(2) 0.0440(14) -0.0258(14) 0.0162(12) -0.0075(14)
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'
Cl Cl 0.1484 0.1585 '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 C8 119.43(17) ?
C1 N1 C2 131.89(18) ?
C1 N1 H1 114.1 ?
C2 N1 H1 114.1 ?
S1 C1 O1 124.56(16) y
S1 C1 N1 122.29(16) y
O1 C1 N1 113.15(18) y
C3 C2 C7 119.1(2) ?
C3 C2 N1 115.72(18) ?
C7 C2 N1 125.2(2) ?
C4 C3 C2 121.0(2) ?
C4 C3 H3 119.5 ?
C2 C3 H3 119.5 ?
C3 C4 C5 119.1(2) ?
C3 C4 H4 120.4 ?
C5 C4 H4 120.4 ?
C6 C5 C4 120.7(2) ?
C6 C5 Cl1 119.76(18) ?
C4 C5 Cl1 119.49(19) ?
C5 C6 C7 120.5(2) ?
C5 C6 H6 119.8 ?
C7 C6 H6 119.8 ?
C6 C7 C2 119.5(2) ?
C6 C7 H7 120.2 ?
C2 C7 H7 120.2 ?
O1 C8 C9 105.69(19) ?
O1 C8 H8A 110.6 ?
C9 C8 H8A 110.6 ?
O1 C8 H8B 110.6 ?
C9 C8 H8B 110.6 ?
H8A C8 H8B 108.7 ?
C8 C9 H9A 109.5 ?
C8 C9 H9B 109.5 ?
H9A C9 H9B 109.5 ?
C8 C9 H9C 109.5 ?
H9A C9 H9C 109.5 ?
H9B C9 H9C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C5 1.740(2) ?
S1 C1 1.667(2) y
O1 C1 1.326(2) y
O1 C8 1.458(3) ?
N1 C1 1.337(3) y
N1 C2 1.417(3) ?
N1 H1 0.8700 ?
C2 C3 1.392(3) ?
C2 C7 1.396(3) ?
C3 C4 1.377(3) ?
C3 H3 0.9400 ?
C4 C5 1.385(3) ?
C4 H4 0.9400 ?
C5 C6 1.370(3) ?
C6 C7 1.386(3) ?
C6 H6 0.9400 ?
C7 H7 0.9400 ?
C8 C9 1.497(3) ?
C8 H8A 0.9800 ?
C8 H8B 0.9800 ?
C9 H9A 0.9700 ?
C9 H9B 0.9700 ?
C9 H9C 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 S1 3_677 0.87 2.60 3.4196(19) 159 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
C8 O1 C1 N1 177.00(19)
C8 O1 C1 S1 -3.7(3)
C2 N1 C1 O1 -4.8(3)
C2 N1 C1 S1 175.85(18)
C1 N1 C2 C3 174.2(2)
C1 N1 C2 C7 -8.0(4)
C7 C2 C3 C4 -2.1(3)
N1 C2 C3 C4 175.9(2)
C2 C3 C4 C5 0.6(4)
C3 C4 C5 C6 1.1(4)
C3 C4 C5 Cl1 -178.97(19)
C4 C5 C6 C7 -1.4(4)
Cl1 C5 C6 C7 178.7(2)
C5 C6 C7 C2 -0.1(4)
C3 C2 C7 C6 1.8(4)
N1 C2 C7 C6 -176.0(2)
C1 O1 C8 C9 -175.0(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21125085
