#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/00/2210027.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_2210027
loop_
_publ_author_name
'Hu, Jing-Han'
'Li, De-Sheng'
'Cao, Cheng'
'Wei, Tai-Bao'
_publ_section_title
;
 1-(4-Ethoxybenzoyl)-3-o-tolylthiourea
;
_journal_coeditor_code           XU2072
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3418
_journal_page_last               o3419
_journal_paper_doi               10.1107/S1600536806027176
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C17 H18 N2 O2 S'
_chemical_formula_moiety         'C17 H18 N2 O2 S'
_chemical_formula_sum            'C17 H18 N2 O2 S'
_chemical_formula_weight         314.39
_chemical_name_systematic
;
1-(4-Ethoxybenzoyl)-3-o-tolylthiourea
;
_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                103.940(10)
_cell_angle_beta                 103.090(10)
_cell_angle_gamma                112.030(10)
_cell_formula_units_Z            2
_cell_length_a                   7.7340(10)
_cell_length_b                   10.198(2)
_cell_length_c                   12.314(2)
_cell_measurement_reflns_used    30
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      17.9
_cell_measurement_theta_min      5.1
_cell_volume                     817.8(3)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1994)'
_computing_data_reduction        'SHELXTL (Bruker, 1998)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.98
_diffrn_measured_fraction_theta_max 0.98
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.010
_diffrn_reflns_av_sigmaI/netI    0.025
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3332
_diffrn_reflns_theta_full        25.5
_diffrn_reflns_theta_max         25.5
_diffrn_reflns_theta_min         1.8
_diffrn_standards_decay_%        3.4
_diffrn_standards_interval_count 97
_diffrn_standards_interval_time  0
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_T_max  0.953
_exptl_absorpt_correction_T_min  0.880
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.38
_refine_diff_density_min         -0.18
_refine_ls_extinction_coef       0.019(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2975
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.052
_refine_ls_R_factor_gt           0.039
_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)+(0.0626P)²+0.0506P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.111
_refine_ls_wR_factor_ref         0.115
_reflns_number_gt                2260
_reflns_number_total             2975
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2072.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        817.9(3)
_cod_database_code               2210027
_cod_database_fobs_code          2210027
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 S 1.02528(7) 0.57617(6) 0.35405(4) 0.0561(2) Uani d . 1
O O1 0.3909(2) 0.21182(19) 0.21506(13) 0.0798(5) Uani d . 1
O O2 0.2471(2) 0.05283(15) 0.66329(12) 0.0619(4) Uani d . 1
N N1 0.6652(2) 0.4382(2) 0.18624(14) 0.0577(5) Uani d . 1
H H1 0.5403 0.3785 0.1648 0.069 Uiso calc R 1
N N2 0.6851(2) 0.39064(17) 0.36085(13) 0.0476(4) Uani d . 1
H H2 0.7506 0.4242 0.4362 0.057 Uiso calc R 1
C C1 0.6324(4) 0.2338(3) -0.0313(2) 0.0945(9) Uani d . 1
H H1A 0.6546 0.1880 -0.1012 0.113 Uiso calc R 1
H H1B 0.4921 0.1893 -0.0451 0.113 Uiso calc R 1
H H1C 0.7003 0.2169 0.0354 0.113 Uiso calc R 1
C C2 0.7107(3) 0.4008(3) -0.00489(19) 0.0677(6) Uani d . 1
C C3 0.7688(4) 0.4627(4) -0.0864(2) 0.0877(9) Uani d . 1
H H3 0.7607 0.3991 -0.1577 0.105 Uiso calc R 1
C C4 0.8371(4) 0.6125(5) -0.0665(3) 0.0976(11) Uani d . 1
H H4 0.8740 0.6501 -0.1237 0.117 Uiso calc R 1
C C5 0.8520(4) 0.7093(4) 0.0388(3) 0.0901(9) Uani d . 1
H H5 0.8979 0.8123 0.0525 0.108 Uiso calc R 1
C C6 0.7983(4) 0.6525(3) 0.1243(2) 0.0714(7) Uani d . 1
H H6 0.8087 0.7169 0.1960 0.086 Uiso calc R 1
C C7 0.7298(3) 0.5004(3) 0.10164(17) 0.0567(5) Uani d . 1
C C8 0.7810(3) 0.4646(2) 0.29470(15) 0.0445(4) Uani d . 1
C C9 0.4971(3) 0.2697(2) 0.32023(18) 0.0525(5) Uani d . 1
C C10 0.4354(3) 0.2144(2) 0.41251(17) 0.0471(5) Uani d . 1
C C11 0.4844(3) 0.3098(2) 0.52767(17) 0.0493(5) Uani d . 1
H H11 0.5643 0.4134 0.5506 0.059 Uiso calc R 1
C C12 0.4162(3) 0.2530(2) 0.60860(18) 0.0520(5) Uani d . 1
H H12 0.4461 0.3185 0.6849 0.062 Uiso calc R 1
C C13 0.3024(3) 0.0978(2) 0.57635(18) 0.0497(5) Uani d . 1
C C14 0.2526(3) 0.0008(2) 0.46141(19) 0.0543(5) Uani d . 1
H H14 0.1762 -0.1031 0.4394 0.065 Uiso calc R 1
C C15 0.3168(3) 0.0593(2) 0.38008(18) 0.0540(5) Uani d . 1
H H15 0.2804 -0.0055 0.3024 0.065 Uiso calc R 1
C C16 0.1374(3) -0.1066(2) 0.6371(2) 0.0612(6) Uani d . 1
H H16A 0.2095 -0.1593 0.6090 0.073 Uiso calc R 1
H H16B 0.0084 -0.1475 0.5751 0.073 Uiso calc R 1
C C17 0.1111(4) -0.1278(3) 0.7493(2) 0.0842(8) Uani d . 1
H H17A 0.2390 -0.0950 0.8078 0.101 Uiso calc R 1
H H17B 0.0288 -0.2331 0.7324 0.101 Uiso calc R 1
H H17C 0.0488 -0.0690 0.7796 0.101 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
C13 O2 C16 118.05(16)
C8 N1 C7 125.80(16)
C8 N1 H1 117.1
C7 N1 H1 117.1
C9 N2 C8 127.92(15)
C9 N2 H2 116.0
C8 N2 H2 116.0
C2 C1 H1A 109.5
C2 C1 H1B 109.5
H1A C1 H1B 109.5
C2 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
C3 C2 C7 116.9(3)
C3 C2 C1 120.7(3)
C7 C2 C1 122.3(2)
C4 C3 C2 122.4(3)
C4 C3 H3 118.8
C2 C3 H3 118.8
C3 C4 C5 119.9(2)
C3 C4 H4 120.0
C5 C4 H4 120.0
C4 C5 C6 119.7(3)
C4 C5 H5 120.1
C6 C5 H5 120.1
C7 C6 C5 119.0(3)
C7 C6 H6 120.5
C5 C6 H6 120.5
C6 C7 C2 122.0(2)
C6 C7 N1 120.0(2)
C2 C7 N1 117.9(2)
N1 C8 N2 115.61(16)
N1 C8 S 125.12(14)
N2 C8 S 119.27(13)
O1 C9 N2 121.99(18)
O1 C9 C10 122.47(18)
N2 C9 C10 115.53(16)
C11 C10 C15 118.80(17)
C11 C10 C9 123.08(17)
C15 C10 C9 118.08(18)
C12 C11 C10 120.72(18)
C12 C11 H11 119.6
C10 C11 H11 119.6
C11 C12 C13 119.99(19)
C11 C12 H12 120.0
C13 C12 H12 120.0
O2 C13 C14 124.61(18)
O2 C13 C12 115.50(18)
C14 C13 C12 119.90(17)
C15 C14 C13 119.59(18)
C15 C14 H14 120.2
C13 C14 H14 120.2
C14 C15 C10 120.94(19)
C14 C15 H15 119.5
C10 C15 H15 119.5
O2 C16 C17 107.94(19)
O2 C16 H16A 110.1
C17 C16 H16A 110.1
O2 C16 H16B 110.1
C17 C16 H16B 110.1
H16A C16 H16B 108.4
C16 C17 H17A 109.5
C16 C17 H17B 109.5
H17A C17 H17B 109.5
C16 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S C8 1.6612(19)
O1 C9 1.219(2)
O2 C13 1.355(2)
O2 C16 1.434(2)
N1 C8 1.328(2)
N1 C7 1.433(2)
N1 H1 0.8600
N2 C9 1.383(2)
N2 C8 1.390(2)
N2 H2 0.8600
C1 C2 1.498(4)
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
C2 C3 1.380(3)
C2 C7 1.390(3)
C3 C4 1.352(4)
C3 H3 0.9300
C4 C5 1.378(4)
C4 H4 0.9300
C5 C6 1.389(3)
C5 H5 0.9300
C6 C7 1.368(3)
C6 H6 0.9300
C9 C10 1.480(3)
C10 C11 1.384(3)
C10 C15 1.394(3)
C11 C12 1.376(2)
C11 H11 0.9300
C12 C13 1.390(3)
C12 H12 0.9300
C13 C14 1.386(3)
C14 C15 1.377(3)
C14 H14 0.9300
C15 H15 0.9300
C16 C17 1.495(3)
C16 H16A 0.9700
C16 H16B 0.9700
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 0.9600
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
N1 H1 O1 . 0.86 1.99 2.649(2) 133
N2 H2 S 2_766 0.86 2.77 3.5712(16) 156
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 -1.5(3)
C1 C2 C3 C4 178.9(2)
C2 C3 C4 C5 0.5(4)
C3 C4 C5 C6 0.5(4)
C4 C5 C6 C7 -0.5(4)
C5 C6 C7 C2 -0.6(3)
C5 C6 C7 N1 -177.2(2)
C3 C2 C7 C6 1.6(3)
C1 C2 C7 C6 -178.9(2)
C3 C2 C7 N1 178.30(18)
C1 C2 C7 N1 -2.2(3)
C8 N1 C7 C6 -67.5(3)
C8 N1 C7 C2 115.7(2)
C7 N1 C8 N2 -179.55(18)
C7 N1 C8 S 0.2(3)
C9 N2 C8 N1 15.5(3)
C9 N2 C8 S -164.23(16)
C8 N2 C9 O1 0.6(3)
C8 N2 C9 C10 179.73(17)
O1 C9 C10 C11 -143.9(2)
N2 C9 C10 C11 37.0(3)
O1 C9 C10 C15 33.9(3)
N2 C9 C10 C15 -145.28(18)
C15 C10 C11 C12 -0.5(3)
C9 C10 C11 C12 177.26(18)
C10 C11 C12 C13 2.2(3)
C16 O2 C13 C14 3.2(3)
C16 O2 C13 C12 -177.16(17)
C11 C12 C13 O2 178.26(17)
C11 C12 C13 C14 -2.1(3)
O2 C13 C14 C15 179.79(18)
C12 C13 C14 C15 0.2(3)
C13 C14 C15 C10 1.6(3)
C11 C10 C15 C14 -1.5(3)
C9 C10 C15 C14 -179.31(18)
C13 O2 C16 C17 174.69(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2629873
