#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/95/2229548.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_2229548
loop_
_publ_author_name
'Saeed, Sohail'
'Rashid, Naghmana'
'Wong, Wing-Tak'
'Hussain, Rizwan'
_publ_section_title
;
 3,5-Dinitro-N-(1,3-thiazol-2-yl)benzamide monohydrate
;
_journal_coeditor_code           XU5155
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o660
_journal_paper_doi               10.1107/S1600536811005228
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C10 H6 N4 O5 S, H2 O'
_chemical_formula_moiety         'C10 H6 N4 O5 S, H2 O'
_chemical_formula_sum            'C10 H8 N4 O6 S'
_chemical_formula_weight         312.26
_chemical_name_systematic
;
3,5-Dinitro-N-(1,3-thiazol-2-yl)benzamide monohydrate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 108.5120(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.7075(12)
_cell_length_b                   6.9734(6)
_cell_length_c                   13.8507(13)
_cell_measurement_reflns_used    9023
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.03
_cell_measurement_theta_min      1.82
_cell_volume                     1255.45(19)
_computing_cell_refinement       'SAINT (Bruker, 2006)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction
;
SAINT (Bruker, 2006) and CrystalStructure (Rigaku/MSC, 2006)
;
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD'
_diffrn_measurement_method       ω
_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  0.0153
_diffrn_reflns_av_sigmaI/netI    0.0158
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6750
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         3.00
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.295
_exptl_absorpt_correction_T_max  0.9825
_exptl_absorpt_correction_T_min  0.9220
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.212
_refine_ls_extinction_coef       0.0069(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2214
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0292
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0569P)²+0.2612P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0827
_refine_ls_wR_factor_ref         0.0879
_reflns_number_gt                1937
_reflns_number_total             2214
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu5155.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2229548
_cod_database_fobs_code          2229548
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 -0.17423(3) 0.90512(6) 0.12088(3) 0.03884(16) Uani d . 1 . .
O O1 0.02312(8) 0.95294(19) 0.11971(8) 0.0469(3) Uani d . 1 . .
O O2 0.35736(11) 1.1250(3) 0.08520(11) 0.0793(5) Uani d . 1 . .
O O3 0.49514(9) 1.0180(3) 0.19517(10) 0.0669(4) Uani d . 1 . .
O O4 0.48076(9) 0.7824(2) 0.51780(10) 0.0590(4) Uani d . 1 . .
O O5 0.34262(11) 0.8314(3) 0.55577(10) 0.0777(5) Uani d . 1 . .
N N1 -0.14748(10) 0.9651(2) 0.31080(10) 0.0403(3) Uani d . 1 . .
N N2 0.00921(9) 0.94048(19) 0.27755(10) 0.0351(3) Uani d . 1 . .
H H2N 0.0335(15) 0.929(3) 0.3435(15) 0.046(5) Uiso d . 1 . .
N N3 0.40286(11) 1.0453(2) 0.16479(11) 0.0505(4) Uani d . 1 . .
N N4 0.39071(10) 0.8282(2) 0.49550(10) 0.0453(4) Uani d . 1 . .
C C1 -0.28028(12) 0.9200(2) 0.16129(13) 0.0425(4) Uani d . 1 . .
H H1 -0.3480 0.9069 0.1193 0.051 Uiso calc R 1 . .
C C2 -0.25176(12) 0.9531(2) 0.26157(13) 0.0429(4) Uani d . 1 . .
H H2 -0.2996 0.9672 0.2960 0.052 Uiso calc R 1 . .
C C3 -0.09807(11) 0.9410(2) 0.24567(11) 0.0331(3) Uani d . 1 . .
C C4 0.06477(11) 0.9452(2) 0.21168(11) 0.0338(3) Uani d . 1 . .
C C5 0.17976(11) 0.9424(2) 0.25696(11) 0.0324(3) Uani d . 1 . .
C C6 0.23598(11) 0.9885(2) 0.19236(12) 0.0368(4) Uani d . 1 . .
H H6 0.2027 1.0230 0.1251 0.044 Uiso calc R 1 . .
C C7 0.34216(11) 0.9820(2) 0.23006(12) 0.0379(4) Uani d . 1 . .
C C8 0.39520(12) 0.9255(2) 0.32777(12) 0.0382(4) Uani d . 1 . .
H H8 0.4665 0.9150 0.3507 0.046 Uiso calc R 1 . .
C C9 0.33678(11) 0.8856(2) 0.38975(11) 0.0352(3) Uani d . 1 . .
C C10 0.23081(11) 0.8948(2) 0.35798(11) 0.0340(3) Uani d . 1 . .
H H10 0.1944 0.8698 0.4029 0.041 Uiso calc R 1 . .
O O6 0.07962(11) 0.8457(2) 0.48713(10) 0.0503(3) Uani d . 1 . .
H H6B 0.0571(18) 0.752(4) 0.4970(18) 0.076(9) Uiso d . 1 . .
H H6C 0.0932(18) 0.912(3) 0.5399(19) 0.073(8) Uiso d . 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'
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'
N N 0.0061 0.0033 '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
C1 S1 C3 . . 88.30(8) ?
C3 N1 C2 . . 109.65(14) ?
C4 N2 C3 . . 123.06(13) ?
C4 N2 H2N . . 126.6(12) ?
C3 N2 H2N . . 110.2(12) ?
O3 N3 O2 . . 124.34(15) ?
O3 N3 C7 . . 117.90(15) ?
O2 N3 C7 . . 117.74(14) ?
O4 N4 O5 . . 123.90(14) ?
O4 N4 C9 . . 118.23(13) ?
O5 N4 C9 . . 117.87(13) ?
C2 C1 S1 . . 110.49(12) ?
C2 C1 H1 . . 124.8 ?
S1 C1 H1 . . 124.8 ?
C1 C2 N1 . . 116.08(14) ?
C1 C2 H2 . . 122.0 ?
N1 C2 H2 . . 122.0 ?
N1 C3 N2 . . 120.67(14) ?
N1 C3 S1 . . 115.47(11) ?
N2 C3 S1 . . 123.84(11) ?
O1 C4 N2 . . 121.63(13) ?
O1 C4 C5 . . 121.21(13) ?
N2 C4 C5 . . 117.15(13) ?
C10 C5 C6 . . 119.83(13) ?
C10 C5 C4 . . 123.35(13) ?
C6 C5 C4 . . 116.81(13) ?
C7 C6 C5 . . 118.77(14) ?
C7 C6 H6 . . 120.6 ?
C5 C6 H6 . . 120.6 ?
C8 C7 C6 . . 123.06(14) ?
C8 C7 N3 . . 117.61(14) ?
C6 C7 N3 . . 119.28(14) ?
C7 C8 C9 . . 116.21(14) ?
C7 C8 H8 . . 121.9 ?
C9 C8 H8 . . 121.9 ?
C8 C9 C10 . . 123.66(14) ?
C8 C9 N4 . . 117.92(14) ?
C10 C9 N4 . . 118.41(13) ?
C9 C10 C5 . . 118.33(13) ?
C9 C10 H10 . . 120.8 ?
C5 C10 H10 . . 120.8 ?
H6B O6 H6C . . 108(2) ?
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 C1 . 1.7187(16) ?
S1 C3 . 1.7304(15) ?
O1 C4 . 1.2205(18) ?
O2 N3 . 1.215(2) ?
O3 N3 . 1.2147(18) ?
O4 N4 . 1.2162(17) ?
O5 N4 . 1.2171(18) ?
N1 C3 . 1.299(2) ?
N1 C2 . 1.377(2) ?
N2 C4 . 1.3618(19) ?
N2 C3 . 1.3947(19) ?
N2 H2N . 0.871(19) ?
N3 C7 . 1.477(2) ?
N4 C9 . 1.471(2) ?
C1 C2 . 1.338(2) ?
C1 H1 . 0.9300 ?
C2 H2 . 0.9300 ?
C4 C5 . 1.500(2) ?
C5 C10 . 1.391(2) ?
C5 C6 . 1.391(2) ?
C6 C7 . 1.382(2) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.375(2) ?
C8 C9 . 1.376(2) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.379(2) ?
C10 H10 . 0.9300 ?
O6 H6B . 0.75(3) ?
O6 H6C . 0.84(3) ?
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 O6 . 0.871(19) 1.974(19) 2.8313(18) 167.9(17)
O6 H6B O1 4_576 0.75(3) 2.38(2) 3.0350(19) 147(2)
O6 H6C N1 3_576 0.84(3) 2.14(3) 2.964(2) 168(2)
