#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:03:29 +0200 (vie 13 de oct de 2017) $
#$Revision: 201974 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/93/2219316.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_2219316
loop_
_publ_author_name
'Corrêa, Rodrigo S.'
'Ribeiro, Leandro'
'Ellena, Javier'
'Estévez-Hernández, Osvaldo'
'Duque, Julio'
_publ_section_title
;
 1-(o-Tolyl)thiourea
;
_journal_coeditor_code           FB2105
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1670
_journal_page_last               o1671
_journal_paper_doi               10.1107/S1600536808024161
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C8 H10 N2 S'
_chemical_formula_moiety         'C8 H10 N2 S'
_chemical_formula_sum            'C8 H10 N2 S'
_chemical_formula_weight         166.25
_chemical_name_systematic
;
1-(o-Tolyl)thiourea
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90.828(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.1323(3)
_cell_length_b                   7.7965(2)
_cell_length_c                   15.3222(4)
_cell_measurement_reflns_used    15611
_cell_measurement_temperature    294
_cell_measurement_theta_max      26.733
_cell_measurement_theta_min      2.91
_cell_volume                     1807.51(8)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) and SCALEPACK'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ scans and ω scans winth κ offsets'
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube Enraf Nonius FR590'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6748
_diffrn_reflns_theta_full        26.77
_diffrn_reflns_theta_max         26.77
_diffrn_reflns_theta_min         3.76
_exptl_absorpt_coefficient_mu    0.296
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   '(Coppens et al.,  1965)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.311
_exptl_crystal_size_mid          0.223
_exptl_crystal_size_min          0.095
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.207
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    40
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1914
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_gt           0.0457
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0896P)²+0.2205P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1401
_reflns_number_gt                1438
_reflns_number_total             1914
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fb2105.cif
_cod_data_source_block           I
_cod_original_cell_volume        1807.61(8)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2219316
_cod_database_fobs_code          2219316
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -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
C C1 0.11314(11) 0.8287(2) 0.06714(12) 0.0577(5) Uani d . 1
C C2 0.15409(11) 0.6359(3) 0.18736(12) 0.0611(5) Uani d . 1
C C3 0.12742(14) 0.4692(3) 0.18788(14) 0.0740(6) Uani d . 1
C C4 0.11722(18) 0.3923(3) 0.27051(17) 0.0886(7) Uani d . 1
H H4 0.0995 0.2783 0.2737 0.106 Uiso calc R 1
C C5 0.13277(17) 0.4810(4) 0.34545(15) 0.0887(7) Uani d . 1
H H5 0.1256 0.4269 0.399 0.106 Uiso calc R 1
C C6 0.15879(16) 0.6486(4) 0.34321(15) 0.0884(7) Uani d . 1
H H6 0.1691 0.7089 0.3947 0.106 Uiso calc R 1
C C7 0.16938(15) 0.7262(3) 0.26419(14) 0.0769(6) Uani d . 1
H H7 0.187 0.8404 0.2618 0.092 Uiso calc R 1
C C8 0.1108(2) 0.3713(4) 0.10584(18) 0.1082(9) Uani d . 1
H H8A 0.0882 0.2598 0.1197 0.162 Uiso calc R 1
H H8B 0.1651 0.3594 0.0748 0.162 Uiso calc R 1
H H8C 0.0685 0.4317 0.0701 0.162 Uiso calc R 1
N N1 0.16917(10) 0.7203(2) 0.10564(10) 0.0665(5) Uani d . 1
H H1 0.218 0.6992 0.0797 0.08 Uiso calc R 1
N N2 0.03568(11) 0.8514(3) 0.10408(12) 0.0897(7) Uani d . 1
H H2A 0.0232 0.797 0.1512 0.108 Uiso calc R 1
H H2B -0.0023 0.9205 0.081 0.108 Uiso calc R 1
S S1 0.14045(3) 0.93276(6) -0.02514(3) 0.0663(2) Uani 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
C1 0.0496(9) 0.0631(10) 0.0607(10) 0.0091(8) 0.0069(8) 0.0058(8)
C2 0.0486(9) 0.0738(12) 0.0610(11) 0.0136(8) 0.0074(8) 0.0143(9)
C3 0.0718(13) 0.0793(14) 0.0711(13) 0.0099(11) 0.0082(10) 0.0043(10)
C4 0.0938(16) 0.0817(14) 0.0906(17) 0.0062(12) 0.0181(14) 0.0225(13)
C5 0.0963(16) 0.1078(18) 0.0624(13) 0.0242(15) 0.0148(11) 0.0210(13)
C6 0.0920(16) 0.1113(19) 0.0619(13) 0.0199(14) 0.0023(11) 0.0010(13)
C7 0.0741(13) 0.0871(14) 0.0696(13) 0.0052(11) 0.0053(10) 0.0012(11)
C8 0.130(2) 0.1022(18) 0.0930(18) -0.0140(18) 0.0182(17) -0.0160(16)
N1 0.0539(8) 0.0834(11) 0.0626(9) 0.0202(7) 0.0146(7) 0.0205(8)
N2 0.0616(10) 0.1243(16) 0.0838(12) 0.0374(10) 0.0250(9) 0.0451(12)
S1 0.0622(4) 0.0697(4) 0.0673(4) 0.0189(2) 0.0158(2) 0.0183(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 0 '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'
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
N2 C1 N1 117.34(16) y
N2 C1 S1 121.63(14) y
N1 C1 S1 121.03(13) y
C3 C2 C7 121.68(19) ?
C3 C2 N1 119.57(19) ?
C7 C2 N1 118.73(19) ?
C2 C3 C4 116.6(2) ?
C2 C3 C8 122.1(2) ?
C4 C3 C8 121.4(2) ?
C5 C4 C3 121.5(2) ?
C5 C4 H4 119.3 ?
C3 C4 H4 119.3 ?
C4 C5 C6 120.9(2) ?
C4 C5 H5 119.6 ?
C6 C5 H5 119.6 ?
C7 C6 C5 119.0(2) ?
C7 C6 H6 120.5 ?
C5 C6 H6 120.5 ?
C6 C7 C2 120.5(2) ?
C6 C7 H7 119.8 ?
C2 C7 H7 119.8 ?
C3 C8 H8A 109.5 ?
C3 C8 H8B 109.5 ?
H8A C8 H8B 109.5 ?
C3 C8 H8C 109.5 ?
H8A C8 H8C 109.5 ?
H8B C8 H8C 109.5 ?
C1 N1 C2 124.75(15) ?
C1 N1 H1 117.6 ?
C2 N1 H1 117.6 ?
C1 N2 H2A 120 ?
C1 N2 H2B 120 ?
H2A N2 H2B 120 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N2 1.321(2) y
C1 N1 1.329(2) y
C1 S1 1.6868(18) y
C2 C3 1.361(3) ?
C2 C7 1.388(3) ?
C2 N1 1.435(2) y
C3 C4 1.411(3) ?
C3 C8 1.489(3) ?
C4 C5 1.358(4) ?
C4 H4 0.93 ?
C5 C6 1.365(4) ?
C5 H5 0.93 ?
C6 C7 1.365(3) ?
C6 H6 0.93 ?
C7 H7 0.93 ?
C8 H8A 0.96 ?
C8 H8B 0.96 ?
C8 H8C 0.96 ?
N1 H1 0.86 ?
N2 H2A 0.86 ?
N2 H2B 0.86 ?
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 7_565 0.86 2.53 3.368(2) 165 y
N2 H2B S1 5_575 0.86 2.52 3.362(2) 166 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
C7 C2 C3 C4 -0.8(3)
N1 C2 C3 C4 177.56(18)
C7 C2 C3 C8 180.0(2)
N1 C2 C3 C8 -1.7(3)
C2 C3 C4 C5 0.4(3)
C8 C3 C4 C5 179.6(3)
C3 C4 C5 C6 0.1(4)
C4 C5 C6 C7 -0.2(4)
C5 C6 C7 C2 -0.1(3)
C3 C2 C7 C6 0.7(3)
N1 C2 C7 C6 -177.68(18)
N2 C1 N1 C2 -4.6(3)
S1 C1 N1 C2 175.28(16)
C3 C2 N1 C1 101.4(2)
C7 C2 N1 C1 -80.2(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2067367
