#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/84/2218493.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_2218493
loop_
_publ_author_name
'Shan, Shang'
'Tian, Yu-Liang'
'Wang, Shan-Heng'
'Wang, Wen-Long'
'Xu, Ying-Li'
_publ_section_title
;
 (E)-Methyl 1,3-thiazol-2-yl ketone 2,4-dinitrophenylhydrazone
;
_journal_coeditor_code           OM2236
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1156
_journal_paper_doi               10.1107/S1600536808015298
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C11 H9 N5 O4 S'
_chemical_formula_moiety         'C11 H9 N5 O4 S'
_chemical_formula_sum            'C11 H9 N5 O4 S'
_chemical_formula_weight         307.29
_chemical_name_systematic
;
(E)-Methyl 1,3-thiazol-2-yl ketone 2,4-dinitrophenylhydrazone
;
_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                 92.610(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.0126(5)
_cell_length_b                   7.3239(4)
_cell_length_c                   21.8683(12)
_cell_measurement_reflns_used    5366
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.5
_cell_measurement_theta_min      3.1
_cell_volume                     1281.98(13)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1993)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID IP'
_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  0.0388
_diffrn_reflns_av_sigmaI/netI    0.0332
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            12253
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.09
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.278
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.592
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.36
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.192
_refine_ls_extinction_coef       0.029(3)
_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   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2943
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0378
_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)+(0.0544P)²+0.1169P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0941
_refine_ls_wR_factor_ref         0.1190
_reflns_number_gt                1845
_reflns_number_total             2943
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            om2236.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2218493
_cod_database_fobs_code          2218493
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
S S1 0.18922(7) 0.17161(8) 0.69372(2) 0.0610(2) Uani d . 1
N N1 0.3851(2) 0.1710(2) 0.39844(7) 0.0550(4) Uani d . 1
N N2 0.9262(2) 0.3699(2) 0.33512(8) 0.0614(5) Uani d . 1
N N3 0.49462(19) 0.2538(2) 0.52598(6) 0.0488(4) Uani d . 1
H H3 0.3946 0.2130 0.5201 0.059 Uiso calc R 1
N N4 0.5583(2) 0.2973(2) 0.58348(7) 0.0523(4) Uani d . 1
N N5 0.20975(19) 0.1562(2) 0.57733(7) 0.0508(4) Uani d . 1
O O1 0.28243(18) 0.1495(2) 0.43763(7) 0.0762(5) Uani d . 1
O O2 0.35547(19) 0.1322(2) 0.34454(7) 0.0777(5) Uani d . 1
O O3 0.8766(2) 0.3374(3) 0.28262(7) 0.0865(5) Uani d . 1
O O4 1.0639(2) 0.4328(2) 0.34849(8) 0.0820(5) Uani d . 1
C C1 0.5967(2) 0.2783(2) 0.47889(8) 0.0436(4) Uani d . 1
C C2 0.5482(2) 0.2422(2) 0.41680(8) 0.0439(4) Uani d . 1
C C3 0.6570(2) 0.2710(2) 0.37046(8) 0.0475(4) Uani d . 1
H H3A 0.6232 0.2463 0.3301 0.057 Uiso calc R 1
C C4 0.8131(2) 0.3355(2) 0.38400(8) 0.0487(5) Uani d . 1
C C5 0.8673(2) 0.3689(3) 0.44448(9) 0.0565(5) Uani d . 1
H H5 0.9754 0.4101 0.4534 0.068 Uiso calc R 1
C C6 0.7610(2) 0.3408(3) 0.49027(8) 0.0531(5) Uani d . 1
H H6 0.7982 0.3638 0.5304 0.064 Uiso calc R 1
C C7 0.4663(2) 0.2727(3) 0.62965(8) 0.0498(4) Uani d . 1
C C8 0.2965(2) 0.2023(2) 0.62794(8) 0.0469(4) Uani d . 1
C C9 0.0559(3) 0.0960(3) 0.59096(9) 0.0571(5) Uani d . 1
H H9 -0.0221 0.0579 0.5608 0.069 Uiso calc R 1
C C10 0.0226(3) 0.0947(3) 0.65099(10) 0.0622(5) Uani d . 1
H H10 -0.0778 0.0568 0.6666 0.075 Uiso calc R 1
C C11 0.5480(3) 0.3213(3) 0.69085(9) 0.0675(6) Uani d . 1
H H11A 0.6545 0.3770 0.6849 0.101 Uiso calc R 1
H H11B 0.5635 0.2127 0.7150 0.101 Uiso calc R 1
H H11C 0.4781 0.4052 0.7116 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
C10 S1 C8 89.63(10)
O1 N1 O2 122.43(17)
O1 N1 C2 118.64(15)
O2 N1 C2 118.92(17)
O4 N2 O3 123.44(18)
O4 N2 C4 118.47(18)
O3 N2 C4 118.07(18)
C1 N3 N4 116.93(15)
C1 N3 H3 121.5
N4 N3 H3 121.5
C7 N4 N3 118.86(16)
C8 N5 C9 110.35(17)
N3 C1 C6 120.08(16)
N3 C1 C2 123.59(16)
C6 C1 C2 116.32(16)
C3 C2 C1 121.21(16)
C3 C2 N1 116.32(15)
C1 C2 N1 122.46(16)
C4 C3 C2 119.92(17)
C4 C3 H3A 120.0
C2 C3 H3A 120.0
C3 C4 C5 120.79(18)
C3 C4 N2 119.92(17)
C5 C4 N2 119.30(18)
C6 C5 C4 119.59(18)
C6 C5 H5 120.2
C4 C5 H5 120.2
C5 C6 C1 122.14(17)
C5 C6 H6 118.9
C1 C6 H6 118.9
N4 C7 C8 126.66(16)
N4 C7 C11 114.95(17)
C8 C7 C11 118.38(17)
N5 C8 C7 124.57(17)
N5 C8 S1 113.67(14)
C7 C8 S1 121.76(13)
C10 C9 N5 115.95(19)
C10 C9 H9 122.0
N5 C9 H9 122.0
C9 C10 S1 110.40(16)
C9 C10 H10 124.8
S1 C10 H10 124.8
C7 C11 H11A 109.5
C7 C11 H11B 109.5
H11A C11 H11B 109.5
C7 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C10 1.691(2) ?
S1 C8 1.7239(19) ?
N1 O1 1.225(2) ?
N1 O2 1.225(2) ?
N1 C2 1.447(2) ?
N2 O4 1.219(2) ?
N2 O3 1.221(2) ?
N2 C4 1.454(2) ?
N3 C1 1.356(2) y
N3 N4 1.373(2) y
N3 H3 0.8600 ?
N4 C7 1.290(2) y
N5 C8 1.324(2) ?
N5 C9 1.355(3) ?
C1 C6 1.405(2) ?
C1 C2 1.420(2) ?
C2 C3 1.383(2) ?
C3 C4 1.357(3) ?
C3 H3A 0.9300 ?
C4 C5 1.395(3) ?
C5 C6 1.359(3) ?
C5 H5 0.9300 ?
C6 H6 0.9300 ?
C7 C8 1.454(3) ?
C7 C11 1.505(3) ?
C9 C10 1.352(3) ?
C9 H9 0.9300 ?
C10 H10 0.9300 ?
C11 H11A 0.9600 ?
C11 H11B 0.9600 ?
C11 H11C 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
_geom_hbond_publ_flag
N3 H3 O1 . 0.86 2.03 2.628(2) 126 y
N3 H3 N5 . 0.86 2.03 2.686(2) 133 y
C9 H9 O1 3_556 0.93 2.58 3.289(3) 133 y
