#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/01/2230180.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_2230180
loop_
_publ_author_name
'Saeed, Sohail'
'Rashid, Naghmana'
'Bhatti, Moazzam H.'
'Wong, Wing-Tak'
_publ_section_title
;
 Ethyl 2-[3-(3,5-Dinitrobenzoyl)thioureido]benzoate
;
_journal_coeditor_code           XU5177
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1114
_journal_paper_doi               10.1107/S1600536811012918
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C17 H14 N4 O7 S'
_chemical_formula_moiety         'C17 H14 N4 O7 S'
_chemical_formula_sum            'C17 H14 N4 O7 S'
_chemical_formula_weight         418.38
_chemical_name_systematic
;
Ethyl 2-[3-(3,5-Dinitrobenzoyl)thioureido]benzoate
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.522(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.7264(19)
_cell_length_b                   16.617(3)
_cell_length_c                   9.9630(16)
_cell_measurement_reflns_used    6458
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      25.02
_cell_measurement_theta_min      2.09
_cell_volume                     1902.2(6)
_computing_cell_refinement       'SAINT (Bruker, 2006)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 2006)'
_computing_molecular_graphics
'ORTEPII (Johnson, 1976) and Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      299(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD'
_diffrn_measurement_method       'ω and φ 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  0.0139
_diffrn_reflns_av_sigmaI/netI    0.0231
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4944
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.74
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_T_max  0.9827
_exptl_absorpt_correction_T_min  0.9432
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.241
_refine_ls_abs_structure_details 'Flack (1983), 1340 Friedel pairs'
_refine_ls_abs_structure_Flack   0.39(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         3011
_refine_ls_number_restraints     42
_refine_ls_restrained_S_all      1.119
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0370
_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)+(0.0536P)²+0.3273P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0906
_refine_ls_wR_factor_ref         0.0945
_reflns_number_gt                2727
_reflns_number_total             3011
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu5177.cif
_cod_data_source_block           I
_cod_original_cell_volume        1902.3(5)
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               2230180
_cod_database_fobs_code          2230180
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'
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_disorder_assembly
_atom_site_disorder_group
S S1 0.94150(8) 0.19793(4) 0.68183(8) 0.0759(3) Uani d . 1 A .
O O2 0.8103(2) 0.05570(13) 1.0967(3) 0.0866(7) Uani d . 1 A .
O O3 0.99391(19) -0.01499(10) 0.97679(18) 0.0663(5) Uani d . 1 A .
O O4 1.0187(3) -0.31100(14) 0.9255(4) 0.1022(8) Uani d . 1 . .
O O5 1.1263(3) -0.35915(14) 0.7937(3) 0.1095(10) Uani d . 1 . .
O O6 1.2496(4) -0.1832(2) 0.4646(3) 0.1355(14) Uani d . 1 . .
O O7 1.2710(4) -0.0571(3) 0.5114(4) 0.1459(15) Uani d . 1 . .
N N1 0.9176(2) 0.13747(12) 0.9269(2) 0.0543(5) Uani d . 1 A .
H H1 0.911(2) 0.0912(17) 0.974(3) 0.064(8) Uiso d . 1 . .
H H2 0.997(2) 0.0472(15) 0.704(3) 0.045(7) Uiso d . 1 . .
N N2 0.9902(2) 0.05353(12) 0.7789(2) 0.0555(5) Uani d . 1 A .
N N3 1.0798(3) -0.30348(14) 0.8423(3) 0.0773(8) Uani d . 1 . .
N N4 1.2402(3) -0.1244(3) 0.5338(3) 0.0976(10) Uani d . 1 . .
C C1 0.7736(3) 0.11786(17) 1.1281(3) 0.0647(7) Uani d . 1 . .
C C2 0.8103(2) 0.19844(15) 1.0865(3) 0.0563(6) Uani d . 1 A .
C C3 0.7770(3) 0.26756(18) 1.1485(3) 0.0713(8) Uani d . 1 . .
H H3 0.7296 0.2626 1.2125 0.086 Uiso calc R 1 A .
C C4 0.8124(4) 0.3418(2) 1.1176(4) 0.0842(10) Uani d . 1 A .
H H4 0.7885 0.3870 1.1596 0.101 Uiso calc R 1 . .
C C5 0.8830(3) 0.35007(17) 1.0248(3) 0.0782(9) Uani d . 1 . .
H H5 0.9080 0.4010 1.0051 0.094 Uiso calc R 1 A .
C C6 0.9179(3) 0.28322(16) 0.9596(3) 0.0657(7) Uani d . 1 A .
H H6 0.9662 0.2896 0.8968 0.079 Uiso calc R 1 . .
C C7 0.8809(2) 0.20717(14) 0.9882(2) 0.0531(6) Uani d . 1 . .
C C8 0.9476(2) 0.13033(14) 0.8043(3) 0.0525(6) Uani d . 1 . .
C C9 1.0156(2) -0.01157(13) 0.8622(2) 0.0518(6) Uani d . 1 . .
C C10 1.0713(2) -0.08065(14) 0.8043(3) 0.0539(6) Uani d . 1 A .
C C11 1.0528(2) -0.15737(14) 0.8509(3) 0.0555(6) Uani d . 1 . .
H H11 1.0103 -0.1650 0.9193 0.067 Uiso calc R 1 A .
C C12 1.0991(2) -0.22190(15) 0.7933(3) 0.0595(7) Uani d . 1 A .
C C13 1.1609(3) -0.21360(18) 0.6905(3) 0.0695(8) Uani d . 1 . .
H H13 1.1890 -0.2582 0.6508 0.083 Uiso calc R 1 A .
C C14 1.1797(3) -0.1366(2) 0.6489(3) 0.0677(8) Uani d . 1 A .
C C15 1.1379(3) -0.07002(16) 0.7053(3) 0.0618(7) Uani d . 1 . .
H H15 1.1542 -0.0186 0.6775 0.074 Uiso calc R 1 A .
O O1 0.7136(10) 0.1247(5) 1.2262(9) 0.083(2) Uani d PDU 0.580(15) A 1
C C16 0.6730(10) 0.0532(7) 1.2838(13) 0.113(4) Uani d PDU 0.580(15) A 1
H H16A 0.6931 0.0548 1.3830 0.135 Uiso calc PR 0.580(15) A 1
H H16B 0.7077 0.0056 1.2523 0.135 Uiso calc PR 0.580(15) A 1
C C17 0.5404(10) 0.0522(6) 1.2345(19) 0.161(6) Uani d PDU 0.580(15) A 1
H H17A 0.5070 0.0125 1.2851 0.193 Uiso calc PR 0.580(15) A 1
H H17B 0.5219 0.0392 1.1387 0.193 Uiso calc PR 0.580(15) A 1
H H17C 0.5093 0.1042 1.2489 0.193 Uiso calc PR 0.580(15) A 1
O O1' 0.6758(12) 0.1178(7) 1.1805(14) 0.085(3) Uani d PDU 0.420(15) A 2
C C16' 0.6436(15) 0.0411(7) 1.2287(14) 0.084(4) Uani d PDU 0.420(15) A 2
H H16C 0.7119 0.0073 1.2549 0.101 Uiso calc PR 0.420(15) A 2
H H16D 0.5889 0.0139 1.1571 0.101 Uiso calc PR 0.420(15) A 2
C C17' 0.5883(19) 0.0568(8) 1.3511(18) 0.134(6) Uani d PDU 0.420(15) A 2
H H17D 0.5738 0.0065 1.3920 0.161 Uiso calc PR 0.420(15) A 2
H H17E 0.5162 0.0850 1.3219 0.161 Uiso calc PR 0.420(15) A 2
H H17F 0.6399 0.0888 1.4169 0.161 Uiso calc PR 0.420(15) A 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 0.0000 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C8 N1 C7 . . 128.5(2) ?
C8 N1 H1 . . 117.1(18) ?
C7 N1 H1 . . 114.0(18) ?
C9 N2 C8 . . 130.7(2) ?
C9 N2 H2 . . 115.4(18) ?
C8 N2 H2 . . 113.8(19) ?
O4 N3 O5 . . 124.6(3) ?
O4 N3 C12 . . 118.4(2) ?
O5 N3 C12 . . 117.1(3) ?
O7 N4 O6 . . 125.1(4) ?
O7 N4 C14 . . 118.6(3) ?
O6 N4 C14 . . 116.2(4) ?
O2 C1 O1 . . 123.2(5) ?
O2 C1 O1' . . 118.9(6) ?
O2 C1 C2 . . 124.7(3) ?
O1 C1 C2 . . 110.8(4) ?
O1' C1 C2 . . 115.0(5) ?
C3 C2 C7 . . 118.5(2) ?
C3 C2 C1 . . 119.6(3) ?
C7 C2 C1 . . 121.9(2) ?
C4 C3 C2 . . 121.5(3) ?
C4 C3 H3 . . 119.2 ?
C2 C3 H3 . . 119.2 ?
C3 C4 C5 . . 120.0(3) ?
C3 C4 H4 . . 120.0 ?
C5 C4 H4 . . 120.0 ?
C4 C5 C6 . . 120.7(3) ?
C4 C5 H5 . . 119.6 ?
C6 C5 H5 . . 119.6 ?
C7 C6 C5 . . 120.0(3) ?
C7 C6 H6 . . 120.0 ?
C5 C6 H6 . . 120.0 ?
C6 C7 C2 . . 119.3(2) ?
C6 C7 N1 . . 121.5(2) ?
C2 C7 N1 . . 119.1(2) ?
N1 C8 N2 . . 114.2(2) ?
N1 C8 S1 . . 129.22(19) ?
N2 C8 S1 . . 116.62(19) ?
O3 C9 N2 . . 123.2(2) ?
O3 C9 C10 . . 121.0(2) ?
N2 C9 C10 . . 115.8(2) ?
C15 C10 C11 . . 120.2(2) ?
C15 C10 C9 . . 122.0(2) ?
C11 C10 C9 . . 117.9(2) ?
C12 C11 C10 . . 118.4(3) ?
C12 C11 H11 . . 120.8 ?
C10 C11 H11 . . 120.8 ?
C13 C12 C11 . . 122.8(3) ?
C13 C12 N3 . . 118.5(2) ?
C11 C12 N3 . . 118.6(3) ?
C12 C13 C14 . . 117.2(2) ?
C12 C13 H13 . . 121.4 ?
C14 C13 H13 . . 121.4 ?
C15 C14 C13 . . 122.3(3) ?
C15 C14 N4 . . 118.1(3) ?
C13 C14 N4 . . 119.5(3) ?
C14 C15 C10 . . 119.0(3) ?
C14 C15 H15 . . 120.5 ?
C10 C15 H15 . . 120.5 ?
C1 O1 C16 . . 119.4(9) ?
O1 C16 C17 . . 106.0(9) ?
O1 C16 H16A . . 110.5 ?
C17 C16 H16A . . 110.5 ?
O1 C16 H16B . . 110.5 ?
C17 C16 H16B . . 110.5 ?
H16A C16 H16B . . 108.7 ?
C1 O1' C16' . . 115.3(10) ?
O1' C16' C17' . . 107.4(10) ?
O1' C16' H16C . . 110.2 ?
C17' C16' H16C . . 110.2 ?
O1' C16' H16D . . 110.2 ?
C17' C16' H16D . . 110.2 ?
H16C C16' H16D . . 108.5 ?
C16' C17' H17D . . 109.5 ?
C16' C17' H17E . . 109.5 ?
H17D C17' H17E . . 109.5 ?
C16' C17' H17F . . 109.5 ?
H17D C17' H17F . . 109.5 ?
H17E C17' H17F . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C8 . 1.649(2) ?
O2 C1 . 1.185(3) ?
O3 C9 . 1.219(3) ?
O4 N3 . 1.205(4) ?
O5 N3 . 1.222(4) ?
O6 N4 . 1.213(4) ?
O7 N4 . 1.210(5) ?
N1 C8 . 1.342(3) ?
N1 C7 . 1.416(3) ?
N1 H1 . 0.91(3) ?
N2 C9 . 1.360(3) ?
N2 C8 . 1.412(3) ?
N2 H2 . 0.77(3) ?
N3 C12 . 1.474(4) ?
N4 C14 . 1.478(4) ?
C1 O1 . 1.318(10) ?
C1 O1' . 1.351(14) ?
C1 C2 . 1.490(4) ?
C2 C3 . 1.396(4) ?
C2 C7 . 1.410(4) ?
C3 C4 . 1.356(5) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.365(5) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.389(4) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.385(4) ?
C6 H6 . 0.9300 ?
C9 C10 . 1.493(3) ?
C10 C15 . 1.386(4) ?
C10 C11 . 1.388(3) ?
C11 C12 . 1.377(4) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.375(4) ?
C13 C14 . 1.376(5) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.375(4) ?
C15 H15 . 0.9300 ?
O1 C16 . 1.442(8) ?
C16 C17 . 1.535(9) ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
O1' C16' . 1.440(9) ?
C16' C17' . 1.514(9) ?
C16' H16C . 0.9700 ?
C16' H16D . 0.9700 ?
C17' H17D . 0.9600 ?
C17' H17E . 0.9600 ?
C17' H17F . 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 O2 . 0.91(3) 1.95(3) 2.672(3) 134(2)
N1 H1 O3 . 0.91(3) 2.01(3) 2.700(3) 131(2)
N2 H2 O3 2_554 0.77(3) 2.32(3) 3.086(3) 172(2)
