#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/58/2235878.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_2235878
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Quah, Ching Kheng'
'Nayak, Prakash S.'
'Narayana, B.'
'Sarojini, B. K.'
_publ_section_title
;
 1-(3-Chlorophenyl)thiourea
;
_journal_coeditor_code           IS5164
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2423
_journal_paper_doi               10.1107/S160053681203084X
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C7 H7 Cl N2 S'
_chemical_formula_moiety         'C7 H7 Cl N2 S'
_chemical_formula_sum            'C7 H7 Cl N2 S'
_chemical_formula_weight         186.66
_chemical_name_systematic
;
1-(3-Chlorophenyl)thiourea
;
_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                104.221(2)
_cell_angle_beta                 91.776(2)
_cell_angle_gamma                96.362(2)
_cell_formula_units_Z            2
_cell_length_a                   5.4406(3)
_cell_length_b                   8.5715(4)
_cell_length_c                   9.2392(4)
_cell_measurement_reflns_used    5475
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.04
_cell_measurement_theta_min      2.91
_cell_volume                     414.33(4)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type
;
Bruker SMART APEXII DUO CCD area-detector
;
_diffrn_measurement_method       'φ and ω scans'
_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  0.0327
_diffrn_reflns_av_sigmaI/netI    0.0308
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8525
_diffrn_reflns_theta_full        30.06
_diffrn_reflns_theta_max         30.06
_diffrn_reflns_theta_min         2.28
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.644
_exptl_absorpt_correction_T_max  0.9563
_exptl_absorpt_correction_T_min  0.7905
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             192
_exptl_crystal_size_max          0.383
_exptl_crystal_size_mid          0.297
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.678
_refine_diff_density_min         -0.374
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         2414
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0310
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0374P)²+0.2220P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0814
_refine_ls_wR_factor_ref         0.0846
_reflns_number_gt                2194
_reflns_number_total             2414
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is5164.cif
_cod_data_source_block           I
_cod_original_cell_volume        414.33(3)
_cod_database_code               2235878
_cod_database_fobs_code          2235878
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
_atom_site_symmetry_multiplicity
Cl Cl1 0.18973(6) 0.42500(4) 1.19169(4) 0.02562(10) Uani d . 1 1
S S1 0.60726(6) 0.24290(3) 0.46595(4) 0.01698(10) Uani d . 1 1
N N1 0.2888(2) 0.14096(13) 0.64519(13) 0.0164(2) Uani d . 1 1
N N2 0.2660(2) 0.39857(14) 0.61960(14) 0.0190(2) Uani d . 1 1
C C1 -0.0855(2) 0.05999(16) 0.76120(15) 0.0181(2) Uani d . 1 1
H H1 -0.1397 -0.0171 0.6730 0.022 Uiso calc R 1 1
C C2 -0.2277(2) 0.07757(17) 0.88598(16) 0.0214(3) Uani d . 1 1
H H2 -0.3772 0.0116 0.8802 0.026 Uiso calc R 1 1
C C3 -0.1494(2) 0.19203(17) 1.01876(15) 0.0201(3) Uani d . 1 1
H H3 -0.2460 0.2046 1.1012 0.024 Uiso calc R 1 1
C C4 0.0770(2) 0.28730(15) 1.02523(14) 0.0172(2) Uani d . 1 1
C C5 0.2222(2) 0.27251(15) 0.90312(15) 0.0167(2) Uani d . 1 1
H H4 0.3731 0.3372 0.9097 0.020 Uiso calc R 1 1
C C6 0.1378(2) 0.15877(14) 0.76997(14) 0.0150(2) Uani d . 1 1
C C7 0.3726(2) 0.26353(14) 0.58419(14) 0.0150(2) Uani d . 1 1
H H2N2 0.147(4) 0.404(3) 0.669(2) 0.033(5) Uiso d . 1 1
H H1N2 0.310(4) 0.479(3) 0.587(2) 0.028(5) Uiso d . 1 1
H H1N1 0.335(4) 0.050(3) 0.610(2) 0.029(5) Uiso d . 1 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'
S S 0.1246 0.1234 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C7 N1 C6 124.20(11)
C7 N1 H1N1 117.8(14)
C6 N1 H1N1 117.9(14)
C7 N2 H2N2 121.1(16)
C7 N2 H1N2 122.5(14)
H2N2 N2 H1N2 116(2)
C6 C1 C2 119.36(12)
C6 C1 H1 120.3
C2 C1 H1 120.3
C3 C2 C1 121.08(12)
C3 C2 H2 119.5
C1 C2 H2 119.5
C2 C3 C4 118.34(12)
C2 C3 H3 120.8
C4 C3 H3 120.8
C5 C4 C3 121.85(12)
C5 C4 Cl1 118.15(10)
C3 C4 Cl1 119.97(10)
C4 C5 C6 118.84(11)
C4 C5 H4 120.6
C6 C5 H4 120.6
C1 C6 C5 120.51(12)
C1 C6 N1 120.46(11)
C5 C6 N1 118.98(11)
N2 C7 N1 117.85(12)
N2 C7 S1 121.69(10)
N1 C7 S1 120.45(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C4 1.7389(13)
S1 C7 1.7021(13)
N1 C7 1.3527(15)
N1 C6 1.4239(16)
N1 H1N1 0.83(2)
N2 C7 1.3257(17)
N2 H2N2 0.80(2)
N2 H1N2 0.84(2)
C1 C6 1.3901(16)
C1 C2 1.3948(19)
C1 H1 0.9300
C2 C3 1.390(2)
C2 H2 0.9300
C3 C4 1.3918(17)
C3 H3 0.9300
C4 C5 1.3855(18)
C5 C6 1.3968(17)
C5 H4 0.9300
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
N2 H2N2 Cl1 2_567 0.80(2) 2.64(2) 3.3583(12) 150(2) yes
N2 H1N2 S1 2_666 0.83(3) 2.54(3) 3.3619(13) 167.5(19) yes
N1 H1N1 S1 2_656 0.84(2) 2.49(3) 3.3149(12) 167(2) yes
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
C6 C1 C2 C3 -0.1(2)
C1 C2 C3 C4 -1.1(2)
C2 C3 C4 C5 1.1(2)
C2 C3 C4 Cl1 -176.81(10)
C3 C4 C5 C6 0.1(2)
Cl1 C4 C5 C6 177.99(10)
C2 C1 C6 C5 1.24(19)
C2 C1 C6 N1 178.69(12)
C4 C5 C6 C1 -1.26(19)
C4 C5 C6 N1 -178.74(11)
C7 N1 C6 C1 126.31(14)
C7 N1 C6 C5 -56.21(18)
C6 N1 C7 N2 -15.51(19)
C6 N1 C7 S1 164.53(10)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2016538
