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###                                                                        ###
###        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.                                        #
#                                                                            #
# 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 2.1.    #
#                                                                            #
# 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/  #
# cif/home.html                                                              #
#                                                                            #
##############################################################################
                                             
data_I
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
(E)-Methyl 3-(2-nitrobenzylidene)dithiocarbazate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C9 H9 N3 O2 S2'
_chemical_formula_sum     'C9 H9 N3 O2 S2'
_chemical_formula_iupac     'C9 H9 N3 O2 S2'
_chemical_formula_weight     255.31
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     7.5261(12)
_cell_length_b     10.7128(16)
_cell_length_c     14.5343(17)
_cell_angle_alpha     78.588(6)
_cell_angle_beta     87.095(5)
_cell_angle_gamma     84.612(6)
_cell_volume     1143.0(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     8768
_cell_measurement_theta_min     3.5
_cell_measurement_theta_max     25.2
_cell_measurement_temperature     291(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.36
_exptl_crystal_size_mid     0.30
_exptl_crystal_size_min     0.16
_exptl_crystal_density_diffrn     1.484
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     528
_exptl_absorpt_coefficient_mu     0.454
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(ABSCOR; Higashi, 1995)'
_exptl_absorpt_correction_T_min     0.795
_exptl_absorpt_correction_T_max     0.930
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     294(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     'Rigaku R-AXIS RAPID IP'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     10.00
_diffrn_reflns_number     11206
_diffrn_reflns_av_R_equivalents     0.0235
_diffrn_reflns_av_sigmaI/netI     0.0308
_diffrn_reflns_theta_min     3.03
_diffrn_reflns_theta_max     27.43
_diffrn_reflns_theta_full     27.43
_diffrn_measured_fraction_theta_max     0.984
_diffrn_measured_fraction_theta_full     0.984
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     18
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     ?
_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 > 2sigma(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     5127
_reflns_number_gt     3773
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0598
_refine_ls_R_factor_gt     0.0409
_refine_ls_wR_factor_gt     0.1008
_refine_ls_wR_factor_ref     0.1159
_refine_ls_goodness_of_fit_ref     1.096
_refine_ls_restrained_S_all     1.096
_refine_ls_number_reflns     5127
_refine_ls_number_parameters     291
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0526P)²+0.2566P] 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     0.002
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.315
_refine_diff_density_min     -0.314
_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     'PROCESS-AUTO (Rigaku, 1998)'
_computing_cell_refinement     'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction     'CrystalStructure (Rigaku/MSC, 2002)'
_computing_structure_solution     'SIR92 (Altomare et al.,  1993)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material     'WinGX (Farrugia, 1999)'
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 -0.10244(10) 0.28477(6) 0.50066(5) 0.0686(2) Uani d . 1 . .
    S S2 -0.04064(8) 0.25046(5) 0.29873(4) 0.05480(17) Uani d . 1 . .
    S S11 0.67348(9) 0.86939(5) 0.15976(5) 0.06155(19) Uani d . 1 . .
    S S12 0.62739(8) 0.64462(5) 0.06773(4) 0.05198(16) Uani d . 1 . .
    N N1 0.1634(3) 0.88846(18) 0.18824(14) 0.0555(5) Uani d . 1 . .
    N N2 0.0369(2) 0.50343(16) 0.26593(12) 0.0470(4) Uani d . 1 . .
    N N3 -0.0124(3) 0.46023(17) 0.35805(13) 0.0545(5) Uani d . 1 . .
    H H3N -0.0185 0.5114 0.3970 0.065 Uiso calc R 1 . .
    N N11 0.3762(3) 0.30552(17) 0.50958(12) 0.0499(4) Uani d . 1 . .
    N N12 0.5421(2) 0.52269(15) 0.24812(12) 0.0420(4) Uani d . 1 . .
    N N13 0.5836(3) 0.64538(16) 0.24503(12) 0.0477(4) Uani d . 1 . .
    H H13N 0.5823 0.6745 0.2961 0.057 Uiso calc R 1 . .
    O O1 0.1188(3) 1.00252(16) 0.16247(14) 0.0801(6) Uani d . 1 . .
    O O2 0.2133(3) 0.84171(18) 0.26726(13) 0.0751(5) Uani d . 1 . .
    O O11 0.4082(3) 0.23524(18) 0.58419(12) 0.0875(7) Uani d . 1 . .
    O O12 0.3194(3) 0.41716(15) 0.50380(12) 0.0646(5) Uani d . 1 . .
    C C1 0.1201(3) 0.67717(18) 0.14835(14) 0.0404(4) Uani d . 1 . .
    C C2 0.1581(3) 0.80514(18) 0.12003(14) 0.0427(4) Uani d . 1 . .
    C C3 0.1920(3) 0.8603(2) 0.02687(15) 0.0496(5) Uani d . 1 . .
    H H3 0.2125 0.9463 0.0103 0.060 Uiso calc R 1 . .
    C C4 0.1951(3) 0.7869(2) -0.04046(16) 0.0535(5) Uani d . 1 . .
    H H4 0.2187 0.8226 -0.1031 0.064 Uiso calc R 1 . .
    C C5 0.1629(3) 0.6593(2) -0.01493(16) 0.0532(5) Uani d . 1 . .
    H H5 0.1668 0.6091 -0.0605 0.064 Uiso calc R 1 . .
    C C6 0.1251(3) 0.6061(2) 0.07770(16) 0.0494(5) Uani d . 1 . .
    H H6 0.1025 0.5205 0.0933 0.059 Uiso calc R 1 . .
    C C7 0.0663(3) 0.6209(2) 0.24519(15) 0.0480(5) Uani d . 1 . .
    H H7 0.0539 0.6708 0.2911 0.058 Uiso calc R 1 . .
    C C8 -0.0516(3) 0.3381(2) 0.38814(16) 0.0504(5) Uani d . 1 . .
    C C9 -0.0977(4) 0.0963(2) 0.3612(2) 0.0689(7) Uani d . 1 . .
    H H9A -0.0182 0.0664 0.4121 0.103 Uiso calc R 1 . .
    H H9B -0.0869 0.0369 0.3193 0.103 Uiso calc R 1 . .
    H H9C -0.2183 0.1032 0.3857 0.103 Uiso calc R 1 . .
    C C11 0.4580(3) 0.32678(17) 0.33941(13) 0.0382(4) Uani d . 1 . .
    C C12 0.4033(3) 0.25252(18) 0.42419(13) 0.0390(4) Uani d . 1 . .
    C C13 0.3699(3) 0.12543(18) 0.43353(15) 0.0453(5) Uani d . 1 . .
    H H13 0.3341 0.0789 0.4914 0.054 Uiso calc R 1 . .
    C C14 0.3904(3) 0.06946(19) 0.35602(16) 0.0514(5) Uani d . 1 . .
    H H14 0.3677 -0.0155 0.3608 0.062 Uiso calc R 1 . .
    C C15 0.4450(3) 0.1400(2) 0.27100(16) 0.0511(5) Uani d . 1 . .
    H H15 0.4585 0.1020 0.2185 0.061 Uiso calc R 1 . .
    C C16 0.4798(3) 0.2658(2) 0.26259(15) 0.0451(5) Uani d . 1 . .
    H H16 0.5186 0.3109 0.2048 0.054 Uiso calc R 1 . .
    C C17 0.5029(3) 0.45918(19) 0.32906(14) 0.0454(5) Uani d . 1 . .
    H H17 0.5028 0.4967 0.3816 0.054 Uiso calc R 1 . .
    C C18 0.6263(3) 0.72055(18) 0.16279(14) 0.0427(5) Uani d . 1 . .
    C C19 0.6919(4) 0.7682(3) -0.02735(17) 0.0663(7) Uani d . 1 . .
    H H19A 0.5985 0.8366 -0.0368 0.099 Uiso calc R 1 . .
    H H19B 0.7119 0.7340 -0.0836 0.099 Uiso calc R 1 . .
    H H19C 0.7996 0.8002 -0.0124 0.099 Uiso calc R 1 . .
_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 . 1.660(2) ?
    S2 C8 . 1.742(3) ?
    S2 C9 . 1.800(2) ?
    S11 C18 . 1.657(2) ?
    S12 C18 . 1.736(2) ?
    S12 C19 . 1.797(2) ?
    N1 O2 . 1.221(3) ?
    N1 O1 . 1.225(2) ?
    N1 C2 . 1.464(3) ?
    N2 C7 . 1.272(3) y
    N2 N3 . 1.372(2) y
    N3 C8 . 1.350(3) y
    N3 H3N . 0.8600 ?
    N11 O11 . 1.212(2) ?
    N11 O12 . 1.220(2) ?
    N11 C12 . 1.461(3) ?
    N12 C17 . 1.273(3) y
    N12 N13 . 1.371(2) y
    N13 C18 . 1.345(2) y
    N13 H13N . 0.8600 ?
    C1 C6 . 1.391(3) ?
    C1 C2 . 1.403(3) ?
    C1 C7 . 1.470(3) ?
    C2 C3 . 1.387(3) ?
    C3 C4 . 1.369(3) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.385(3) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.381(3) ?
    C5 H5 . 0.9300 ?
    C6 H6 . 0.9300 ?
    C7 H7 . 0.9300 ?
    C9 H9A . 0.9600 ?
    C9 H9B . 0.9600 ?
    C9 H9C . 0.9600 ?
    C11 C12 . 1.394(3) ?
    C11 C16 . 1.396(3) ?
    C11 C17 . 1.466(3) ?
    C12 C13 . 1.387(3) ?
    C13 C14 . 1.373(3) ?
    C13 H13 . 0.9300 ?
    C14 C15 . 1.380(3) ?
    C14 H14 . 0.9300 ?
    C15 C16 . 1.378(3) ?
    C15 H15 . 0.9300 ?
    C16 H16 . 0.9300 ?
    C17 H17 . 0.9300 ?
    C19 H19A . 0.9600 ?
    C19 H19B . 0.9600 ?
    C19 H19C . 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
    C8 S2 C9 . . 101.93(12) ?
    C18 S12 C19 . . 101.57(11) ?
    O2 N1 O1 . . 123.3(2) ?
    O2 N1 C2 . . 118.83(19) ?
    O1 N1 C2 . . 117.9(2) ?
    C7 N2 N3 . . 115.10(19) ?
    C8 N3 N2 . . 120.7(2) ?
    C8 N3 H3N . . 119.7 ?
    N2 N3 H3N . . 119.7 ?
    O11 N11 O12 . . 122.41(19) ?
    O11 N11 C12 . . 118.20(18) ?
    O12 N11 C12 . . 119.38(17) ?
    C17 N12 N13 . . 115.97(17) ?
    C18 N13 N12 . . 120.58(17) ?
    C18 N13 H13N . . 119.7 ?
    N12 N13 H13N . . 119.7 ?
    C6 C1 C2 . . 116.07(19) ?
    C6 C1 C7 . . 120.58(18) ?
    C2 C1 C7 . . 123.24(19) ?
    C3 C2 C1 . . 122.61(19) ?
    C3 C2 N1 . . 116.12(17) ?
    C1 C2 N1 . . 121.27(18) ?
    C4 C3 C2 . . 119.33(19) ?
    C4 C3 H3 . . 120.3 ?
    C2 C3 H3 . . 120.3 ?
    C3 C4 C5 . . 119.7(2) ?
    C3 C4 H4 . . 120.1 ?
    C5 C4 H4 . . 120.1 ?
    C6 C5 C4 . . 120.4(2) ?
    C6 C5 H5 . . 119.8 ?
    C4 C5 H5 . . 119.8 ?
    C5 C6 C1 . . 121.75(19) ?
    C5 C6 H6 . . 119.1 ?
    C1 C6 H6 . . 119.1 ?
    N2 C7 C1 . . 119.6(2) ?
    N2 C7 H7 . . 120.2 ?
    C1 C7 H7 . . 120.2 ?
    N3 C8 S1 . . 120.37(19) ?
    N3 C8 S2 . . 113.24(16) ?
    S1 C8 S2 . . 126.39(13) ?
    S2 C9 H9A . . 109.5 ?
    S2 C9 H9B . . 109.5 ?
    H9A C9 H9B . . 109.5 ?
    S2 C9 H9C . . 109.5 ?
    H9A C9 H9C . . 109.5 ?
    H9B C9 H9C . . 109.5 ?
    C12 C11 C16 . . 116.26(17) ?
    C12 C11 C17 . . 123.88(18) ?
    C16 C11 C17 . . 119.74(18) ?
    C13 C12 C11 . . 123.03(19) ?
    C13 C12 N11 . . 115.63(18) ?
    C11 C12 N11 . . 121.34(17) ?
    C14 C13 C12 . . 118.95(19) ?
    C14 C13 H13 . . 120.5 ?
    C12 C13 H13 . . 120.5 ?
    C13 C14 C15 . . 119.60(19) ?
    C13 C14 H14 . . 120.2 ?
    C15 C14 H14 . . 120.2 ?
    C16 C15 C14 . . 121.1(2) ?
    C16 C15 H15 . . 119.5 ?
    C14 C15 H15 . . 119.5 ?
    C15 C16 C11 . . 121.1(2) ?
    C15 C16 H16 . . 119.5 ?
    C11 C16 H16 . . 119.5 ?
    N12 C17 C11 . . 119.89(18) ?
    N12 C17 H17 . . 120.1 ?
    C11 C17 H17 . . 120.1 ?
    N13 C18 S11 . . 120.14(16) ?
    N13 C18 S12 . . 113.32(14) ?
    S11 C18 S12 . . 126.54(12) ?
    S12 C19 H19A . . 109.5 ?
    S12 C19 H19B . . 109.5 ?
    H19A C19 H19B . . 109.5 ?
    S12 C19 H19C . . 109.5 ?
    H19A C19 H19C . . 109.5 ?
    H19B C19 H19C . . 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
    _geom_hbond_publ_flag
    N13 H13N O11 2_666 0.86 2.16 3.014(3) 174 y
    C17 H17 O12 2_666 0.93 2.55 3.373(3) 148 y
data_global
_journal_date_recd_electronic     2007-11-17
_journal_date_accepted     2007-11-19
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      1
_journal_page_first     o53
_journal_page_last     o53
_journal_paper_category     QO
_journal_coeditor_code     NG2380
_publ_contact_author_name     'Dr Shang Shan'
_publ_contact_author_address
;
College of Chemical Engineering and Materials Science
Zhejiang University of Technology
People's Republic of China
;
_publ_contact_author_email     shanshang@mail.hz.zj.cn
_publ_section_title
;
(E)-Methyl 3-(2-nitrobenzylidene)dithiocarbazate
;
loop_
    _publ_author_name
    _publ_author_address
    'Shang Shan'
;
College of Chemical Engineering and Materials Science
Zhejiang University of Technology
People's Republic of China
;
    'Yu-Liang Tian'
;
College of Chemical Engineering and Materials Science
Zhejiang University of Technology
People's Republic of China
;
    'Wen-Long Wang'
;
College of Chemical Engineering and Materials Science
Zhejiang University of Technology
People's Republic of China
;
    'Shan-Heng Wang'
;
College of Chemical Engineering and Materials Science
Zhejiang University of Technology
People's Republic of China
;
