##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
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# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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data_global
_audit_creation_method     'SHELXL97'
_journal_date_recd_electronic     2010-03-11
_journal_date_accepted     2010-03-24
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      4
_journal_page_first     o980
_journal_page_last     o980
_journal_paper_category     QO
_journal_coeditor_code     SI2248
_publ_contact_author_name     'Sohail Saeed'
_publ_contact_author_address
;
Department of Chemistry, Research Complex,
Allama Iqbal Open University,
Islamabad,
Pakistan
;
_publ_contact_author_email     'Sohail262001@yahoo.com'
_publ_contact_author_fax     '(092)51-925-0081'
_publ_contact_author_phone     '(092)51-925-0081'
_publ_section_title
;
Ethyl 2-[3-(4-nitrobenzoyl)thioureido]benzoate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Saeed, Sohail' .
;
Department of Chemistry, Research Complex,
Allama Iqbal Open University,
Islamabad,
Pakistan
;
    'Rashid, Naghmana' .
;
Department of Chemistry, Research Complex,
Allama Iqbal Open University,
Islamabad,
Pakistan
;
    'Wong, Wing-Tak ' .
;
Department of Applied Biology and Chemical Technology
The Hong Kong Polytechnic University
Hung Hom, Kowloon,
Hong Kong SAR,
People's Republic of China
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
Ethyl 2-[3-(4-nitrobenzoyl)thioureido]benzoate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C17 H15 N3 O5 S'
_chemical_formula_sum     'C17 H15 N3 O5 S'
_chemical_formula_iupac     'C17 H15 N3 O5 S'
_chemical_formula_weight     373.38
_chemical_melting_point     438
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P b c a'
_symmetry_space_group_name_Hall     '-P 2ac 2ab'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, z'
    'x, -y+1/2, z+1/2'
    '-x+1/2, -y, z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, -z'
    '-x, y-1/2, -z-1/2'
    'x-1/2, y, -z-1/2'
_cell_length_a     9.0698(13)
_cell_length_b     15.778(2)
_cell_length_c     24.889(4)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     3561.7(9)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     23121
_cell_measurement_theta_min     1.64
_cell_measurement_theta_max     28.28
_cell_measurement_temperature     295(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.36
_exptl_crystal_size_mid     0.25
_exptl_crystal_size_min     0.03
_exptl_crystal_density_diffrn     1.393
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1552
_exptl_absorpt_coefficient_mu     0.215
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.9265
_exptl_absorpt_correction_T_max     0.9936
_exptl_special_details
;
;
_diffrn_ambient_temperature     295(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART 1000 CCD'
_diffrn_measurement_method     'ω scan'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     23121
_diffrn_reflns_av_R_equivalents     0.0322
_diffrn_reflns_av_sigmaI/netI     0.0284
_diffrn_reflns_theta_min     1.64
_diffrn_reflns_theta_max     28.28
_diffrn_reflns_theta_full     28.28
_diffrn_measured_fraction_theta_max     0.988
_diffrn_measured_fraction_theta_full     0.988
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -21
_diffrn_reflns_limit_k_max     21
_diffrn_reflns_limit_l_min     -33
_diffrn_reflns_limit_l_max     32
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     0
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors
based on F² are statistically about twice as large as those based on
F, and R- factors based on ALL data will be even larger.
;
_reflns_number_total     4362
_reflns_number_gt     2877
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0884
_refine_ls_R_factor_gt     0.0593
_refine_ls_wR_factor_gt     0.1540
_refine_ls_wR_factor_ref     0.1705
_refine_ls_goodness_of_fit_ref     1.066
_refine_ls_restrained_S_all     1.183
_refine_ls_number_reflns     4362
_refine_ls_number_parameters     244
_refine_ls_number_restraints     6
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0709P)²+2.2491P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.634
_refine_diff_density_min     -0.324
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'SMART (Bruker, 1998)'
_computing_cell_refinement     'SAINT (Bruker, 2006)'
_computing_data_reduction
       'SAINT (Bruker, 2006) and CrystalStructure (Rigaku/MSC and Rigaku, 2006)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'ORTEPII (Johnson, 1976)'
_computing_publication_material     'SHELXL97 (Sheldrick, 2008)'
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 0.51557(9) 0.11637(5) 0.20685(4) 0.0587(3) Uani d . 1 . .
    O O1 0.3603(6) 0.5330(3) 0.44429(14) 0.1331(16) Uani d . 1 . .
    O O2 0.1862(4) 0.6034(2) 0.40527(18) 0.1245(13) Uani d U 1 . .
    O O3 0.1165(2) 0.29106(13) 0.21392(8) 0.0476(5) Uani d . 1 . .
    O O4 0.0879(3) 0.24551(13) 0.09489(9) 0.0641(6) Uani d . 1 . .
    O O5 0.0925(3) 0.19226(14) 0.01211(9) 0.0662(7) Uani d . 1 . .
    N N1 0.2655(5) 0.5415(2) 0.41024(19) 0.0936(13) Uani d . 1 . .
    N N2 0.3396(2) 0.23826(15) 0.23814(10) 0.0428(5) Uani d . 1 . .
    N N3 0.2463(3) 0.15722(15) 0.16898(9) 0.0414(5) Uani d . 1 . .
    C C1 0.2484(4) 0.4741(2) 0.36882(15) 0.0648(9) Uani d . 1 . .
    C C2 0.1512(4) 0.4866(2) 0.32689(17) 0.0690(10) Uani d . 1 . .
    H H2 0.0937 0.5353 0.3250 0.083 Uiso calc R 1 . .
    C C3 0.1416(4) 0.4242(2) 0.28770(13) 0.0552(8) Uani d . 1 . .
    H H3 0.0758 0.4306 0.2593 0.066 Uiso calc R 1 . .
    C C4 0.2296(3) 0.35235(17) 0.29062(11) 0.0423(6) Uani d . 1 . .
    C C5 0.3214(3) 0.3409(2) 0.33479(12) 0.0516(7) Uani d . 1 . .
    H H5 0.3764 0.2914 0.3379 0.062 Uiso calc R 1 . .
    C C6 0.3312(4) 0.4026(2) 0.37399(13) 0.0630(9) Uani d . 1 . .
    H H6 0.3932 0.3955 0.4034 0.076 Uiso calc R 1 . .
    C C7 0.2219(3) 0.29142(16) 0.24481(10) 0.0388(6) Uani d . 1 . .
    C C8 0.3576(3) 0.17016(17) 0.20286(10) 0.0411(6) Uani d . 1 . .
    C C9 0.2299(3) 0.08868(17) 0.13261(11) 0.0423(6) Uani d . 1 . .
    C C10 0.2679(4) 0.00680(19) 0.14754(13) 0.0575(8) Uani d . 1 . .
    H H10 0.3060 -0.0030 0.1817 0.069 Uiso calc R 1 . .
    C C11 0.2504(4) -0.0600(2) 0.11286(15) 0.0661(9) Uani d . 1 . .
    H H11 0.2767 -0.1144 0.1236 0.079 Uiso calc R 1 . .
    C C12 0.1938(4) -0.0466(2) 0.06204(15) 0.0659(9) Uani d . 1 . .
    H H12 0.1837 -0.0916 0.0382 0.079 Uiso calc R 1 . .
    C C13 0.1526(4) 0.03375(19) 0.04696(13) 0.0552(8) Uani d . 1 . .
    H H13 0.1138 0.0424 0.0128 0.066 Uiso calc R 1 . .
    C C14 0.1677(3) 0.10259(17) 0.08161(11) 0.0435(6) Uani d . 1 . .
    C C15 0.1132(3) 0.18718(18) 0.06483(12) 0.0472(7) Uani d . 1 . .
    C C16 0.0290(5) 0.2705(2) -0.00865(15) 0.0782(11) Uani d . 1 . .
    H H16A 0.0907 0.3184 0.0010 0.094 Uiso calc R 1 . .
    H H16B -0.0684 0.2794 0.0064 0.094 Uiso calc R 1 . .
    C C17 0.0198(5) 0.2627(3) -0.06722(17) 0.0872(13) Uani d . 1 . .
    H H17A -0.0220 0.3135 -0.0820 0.105 Uiso calc R 1 . .
    H H17B -0.0414 0.2152 -0.0763 0.105 Uiso calc R 1 . .
    H H17C 0.1168 0.2543 -0.0817 0.105 Uiso calc R 1 . .
    H H2N 0.409(4) 0.2503(19) 0.2566(13) 0.047(9) Uiso d . 1 . .
    H H3N 0.177(3) 0.200(2) 0.1694(12) 0.050(8) Uiso 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
    S1 0.0427(4) 0.0648(5) 0.0686(5) 0.0143(3) -0.0073(4) -0.0180(4)
    O1 0.208(5) 0.116(3) 0.075(2) -0.037(3) -0.004(3) -0.037(2)
    O2 0.099(2) 0.104(2) 0.171(3) -0.0053(18) 0.0240(19) -0.073(2)
    O3 0.0353(10) 0.0564(12) 0.0511(11) 0.0026(8) -0.0027(8) 0.0000(9)
    O4 0.0893(17) 0.0445(12) 0.0584(13) 0.0126(11) -0.0185(12) -0.0062(10)
    O5 0.0994(19) 0.0516(13) 0.0476(12) 0.0076(12) -0.0137(12) 0.0037(10)
    N1 0.094(3) 0.073(2) 0.114(3) -0.026(2) 0.042(2) -0.039(2)
    N2 0.0302(11) 0.0540(14) 0.0442(13) 0.0015(10) -0.0021(10) -0.0106(10)
    N3 0.0400(12) 0.0416(12) 0.0425(12) 0.0015(10) -0.0035(10) -0.0026(10)
    C1 0.065(2) 0.062(2) 0.067(2) -0.0163(17) 0.0258(18) -0.0232(17)
    C2 0.066(2) 0.0466(18) 0.094(3) 0.0033(15) 0.027(2) -0.0093(18)
    C3 0.0485(17) 0.0510(17) 0.0661(19) 0.0060(13) 0.0097(15) 0.0010(15)
    C4 0.0356(13) 0.0448(14) 0.0466(14) -0.0019(11) 0.0115(11) -0.0026(12)
    C5 0.0468(16) 0.0601(18) 0.0479(16) 0.0042(13) 0.0045(13) -0.0090(14)
    C6 0.058(2) 0.083(2) 0.0482(17) -0.0072(18) 0.0094(15) -0.0178(16)
    C7 0.0310(12) 0.0442(14) 0.0410(13) -0.0020(10) 0.0057(11) 0.0024(11)
    C8 0.0379(13) 0.0476(15) 0.0378(13) -0.0009(11) 0.0031(11) -0.0008(11)
    C9 0.0416(14) 0.0404(14) 0.0448(14) -0.0014(11) 0.0001(12) -0.0015(11)
    C10 0.068(2) 0.0458(16) 0.0589(19) 0.0016(15) -0.0138(16) 0.0046(14)
    C11 0.079(2) 0.0407(17) 0.079(2) 0.0046(16) -0.0134(19) 0.0007(15)
    C12 0.086(3) 0.0419(17) 0.070(2) 0.0032(16) -0.0107(19) -0.0121(15)
    C13 0.067(2) 0.0484(17) 0.0496(16) 0.0006(14) -0.0096(15) -0.0070(13)
    C14 0.0460(15) 0.0416(14) 0.0429(14) -0.0026(11) -0.0026(12) -0.0010(11)
    C15 0.0489(16) 0.0447(16) 0.0481(16) -0.0025(12) -0.0088(13) 0.0004(12)
    C16 0.107(3) 0.059(2) 0.069(2) 0.012(2) -0.021(2) 0.0121(18)
    C17 0.103(3) 0.083(3) 0.076(3) -0.005(2) -0.026(2) 0.021(2)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes) are
estimated using the full covariance matrix. The cell esds are taken into
account individually in the estimation of esds in distances, angles and
torsion angles; correlations between esds in cell parameters are only used
when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 . 1.668(3) ?
    O1 N1 . 1.215(6) ?
    O2 N1 . 1.219(5) ?
    O3 C7 . 1.227(3) ?
    O4 C15 . 1.208(3) ?
    O5 C15 . 1.328(3) ?
    O5 C16 . 1.457(4) ?
    N1 C1 . 1.489(5) ?
    N2 C7 . 1.368(3) ?
    N2 C8 . 1.397(3) ?
    N2 H2N . 0.80(3) ?
    N3 C8 . 1.331(3) ?
    N3 C9 . 1.418(3) ?
    N3 H3N . 0.91(3) ?
    C1 C6 . 1.361(5) ?
    C1 C2 . 1.380(6) ?
    C2 C3 . 1.388(5) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.388(4) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.391(4) ?
    C4 C7 . 1.493(4) ?
    C5 C6 . 1.381(4) ?
    C5 H5 . 0.9300 ?
    C6 H6 . 0.9300 ?
    C9 C10 . 1.388(4) ?
    C9 C14 . 1.406(4) ?
    C10 C11 . 1.371(4) ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.381(5) ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.373(5) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.394(4) ?
    C13 H13 . 0.9300 ?
    C14 C15 . 1.483(4) ?
    C16 C17 . 1.465(6) ?
    C16 H16A . 0.9700 ?
    C16 H16B . 0.9700 ?
    C17 H17A . 0.9600 ?
    C17 H17B . 0.9600 ?
    C17 H17C . 0.9600 ?
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
    C15 O5 C16 . . 117.2(3) ?
    O1 N1 O2 . . 125.2(4) ?
    O1 N1 C1 . . 118.6(4) ?
    O2 N1 C1 . . 116.1(5) ?
    C7 N2 C8 . . 129.7(2) ?
    C7 N2 H2N . . 113(2) ?
    C8 N2 H2N . . 117(2) ?
    C8 N3 C9 . . 126.9(2) ?
    C8 N3 H3N . . 113.5(19) ?
    C9 N3 H3N . . 119.5(19) ?
    C6 C1 C2 . . 122.8(3) ?
    C6 C1 N1 . . 117.9(4) ?
    C2 C1 N1 . . 119.2(4) ?
    C1 C2 C3 . . 118.0(3) ?
    C1 C2 H2 . . 121.0 ?
    C3 C2 H2 . . 121.0 ?
    C2 C3 C4 . . 120.4(3) ?
    C2 C3 H3 . . 119.8 ?
    C4 C3 H3 . . 119.8 ?
    C3 C4 C5 . . 119.4(3) ?
    C3 C4 C7 . . 117.3(3) ?
    C5 C4 C7 . . 123.2(2) ?
    C6 C5 C4 . . 120.4(3) ?
    C6 C5 H5 . . 119.8 ?
    C4 C5 H5 . . 119.8 ?
    C1 C6 C5 . . 118.8(3) ?
    C1 C6 H6 . . 120.6 ?
    C5 C6 H6 . . 120.6 ?
    O3 C7 N2 . . 122.0(2) ?
    O3 C7 C4 . . 121.2(2) ?
    N2 C7 C4 . . 116.8(2) ?
    N3 C8 N2 . . 115.3(2) ?
    N3 C8 S1 . . 127.7(2) ?
    N2 C8 S1 . . 117.0(2) ?
    C10 C9 C14 . . 119.1(3) ?
    C10 C9 N3 . . 120.9(3) ?
    C14 C9 N3 . . 119.9(2) ?
    C11 C10 C9 . . 121.2(3) ?
    C11 C10 H10 . . 119.4 ?
    C9 C10 H10 . . 119.4 ?
    C10 C11 C12 . . 120.1(3) ?
    C10 C11 H11 . . 119.9 ?
    C12 C11 H11 . . 119.9 ?
    C13 C12 C11 . . 119.5(3) ?
    C13 C12 H12 . . 120.2 ?
    C11 C12 H12 . . 120.2 ?
    C12 C13 C14 . . 121.6(3) ?
    C12 C13 H13 . . 119.2 ?
    C14 C13 H13 . . 119.2 ?
    C13 C14 C9 . . 118.4(3) ?
    C13 C14 C15 . . 119.6(3) ?
    C9 C14 C15 . . 121.9(2) ?
    O4 C15 O5 . . 122.6(3) ?
    O4 C15 C14 . . 125.1(3) ?
    O5 C15 C14 . . 112.3(2) ?
    O5 C16 C17 . . 107.7(3) ?
    O5 C16 H16A . . 110.2 ?
    C17 C16 H16A . . 110.2 ?
    O5 C16 H16B . . 110.2 ?
    C17 C16 H16B . . 110.2 ?
    H16A C16 H16B . . 108.5 ?
    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_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
    N2 H2N O3 8_656 0.80(4) 2.12(4) 2.903(3) 165(3)
    N3 H3N O3 . 0.91(3) 1.91(3) 2.664(3) 139(3)
    N3 H3N O4 . 0.91(3) 2.15(3) 2.721(3) 120(2)
