##############################################################################
#                                                                            #
# 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 Acta Crystallographica 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.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     SHELXL-2014/6
_chemical_name_systematic
;
(E)-N'-(2-Chlorobenzylidene)-4-nitrobenzenesulfonohydrazide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C13 H10 Cl N3 O4 S'
_chemical_formula_sum     'C13 H10 Cl N3 O4 S'
_chemical_formula_iupac     'C13 H10 Cl N3 O4 S'
_chemical_formula_weight     339.75
_chemical_melting_point     ?
_chemical_absolute_configuration     ?
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21'
_space_group_name_Hall     'P 2yb'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y+1/2, -z'
_cell_length_a     4.9498(6)
_cell_length_b     22.340(3)
_cell_length_c     7.0003(9)
_cell_angle_alpha     90
_cell_angle_beta     104.400(10)
_cell_angle_gamma     90
_cell_volume     749.76(17)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     1264
_cell_measurement_theta_min     2.99
_cell_measurement_theta_max     27.68
_cell_measurement_temperature     293(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.240
_exptl_crystal_size_mid     0.240
_exptl_crystal_size_min     0.120
_exptl_crystal_density_diffrn     1.505
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     348
_exptl_absorpt_coefficient_mu     0.415
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2009)
;
_exptl_absorpt_correction_T_min     0.907
_exptl_absorpt_correction_T_max     0.952
_diffrn_ambient_temperature     293(2)
_diffrn_source     'Enhance (Mo) X-ray Source'
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur single crystal X-ray diffractometer
with Sapphire CCD detector
;
_diffrn_measurement_method
;
Rotation method data acquisition using omega scans.
;
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     4582
_diffrn_reflns_av_R_equivalents     0.0149
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_theta_min     3.004
_diffrn_reflns_theta_max     25.350
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.991
_diffrn_measured_fraction_theta_full     0.991
_diffrn_reflns_limit_h_min     -3
_diffrn_reflns_limit_h_max     5
_diffrn_reflns_limit_k_min     -26
_diffrn_reflns_limit_k_max     26
_diffrn_reflns_limit_l_min     -8
_diffrn_reflns_limit_l_max     7
_refine_special_details     ?
_reflns_number_total     2696
_reflns_number_gt     2457
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0355
_refine_ls_R_factor_gt     0.0304
_refine_ls_wR_factor_gt     0.0753
_refine_ls_wR_factor_ref     0.0778
_refine_ls_goodness_of_fit_ref     1.008
_refine_ls_restrained_S_all     1.008
_refine_ls_number_reflns     2696
_refine_ls_number_parameters     202
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0489P)²+0.0544P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_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     0.140
_refine_diff_density_min     -0.199
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
_refine_ls_abs_structure_details
;
Flack x determined using 1102 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack     0.05(3)
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'
    'Cl' 'Cl' 0.1484 0.1585
                         '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
;
CrysAlis CCD (Oxford Diffraction, 2009)
;
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_structure_solution
;
SHELXS2013 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015)
;
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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Cl Cl1 0.0897(2) -0.10843(5) 0.44188(16) 0.0737(3) Uani d 1 . .
    S S1 0.59163(16) 0.12968(4) 0.08796(12) 0.0429(2) Uani d 1 . .
    O O1 0.8691(5) 0.11233(13) 0.0900(4) 0.0603(7) Uani d 1 . .
    O O2 0.4169(5) 0.15582(12) -0.0845(3) 0.0519(6) Uani d 1 . .
    O O3 0.8117(8) 0.27393(16) 0.9402(5) 0.0788(9) Uani d 1 . .
    O O4 0.4147(8) 0.3096(2) 0.7925(5) 0.1064(14) Uani d 1 . .
    N N1 0.4239(6) 0.07005(13) 0.1288(4) 0.0445(7) Uani d 1 . .
    H H1N 0.248(5) 0.0750(18) 0.109(5) 0.053 Uiso d 1 . .
    N N2 0.5519(6) 0.04007(13) 0.3042(4) 0.0472(7) Uani d 1 . .
    N N3 0.6159(8) 0.27887(16) 0.7968(5) 0.0619(9) Uani d 1 . .
    C C1 0.6093(7) 0.17729(15) 0.2929(5) 0.0411(7) Uani d 1 . .
    C C2 0.8188(7) 0.16808(16) 0.4642(5) 0.0480(8) Uani d 1 . .
    H H2 0.9556 0.1393 0.4672 0.058 Uiso calc 1 . .
    C C3 0.8216(7) 0.20189(17) 0.6288(5) 0.0509(9) Uani d 1 . .
    H H3 0.9590 0.1963 0.7451 0.061 Uiso calc 1 . .
    C C4 0.6175(8) 0.24394(16) 0.6174(5) 0.0467(8) Uani d 1 . .
    C C5 0.4109(8) 0.25443(17) 0.4481(6) 0.0517(9) Uani d 1 . .
    H H5 0.2762 0.2836 0.4456 0.062 Uiso calc 1 . .
    C C6 0.4083(8) 0.22071(16) 0.2829(5) 0.0479(8) Uani d 1 . .
    H H6 0.2728 0.2271 0.1662 0.057 Uiso calc 1 . .
    C C7 0.3937(8) 0.00577(16) 0.3719(6) 0.0498(9) Uani d 1 . .
    H H7 0.2072 0.0013 0.3054 0.060 Uiso calc 1 . .
    C C8 0.5085(8) -0.02677(16) 0.5566(5) 0.0504(9) Uani d 1 . .
    C C9 0.3835(9) -0.07856(17) 0.6049(6) 0.0553(9) Uani d 1 . .
    C C10 0.4901(10) -0.1087(2) 0.7781(6) 0.0719(11) Uani d 1 . .
    H H10 0.4014 -0.1428 0.8084 0.086 Uiso calc 1 . .
    C C11 0.7282(13) -0.0882(2) 0.9061(7) 0.0875(17) Uani d 1 . .
    H H11 0.8007 -0.1084 1.0237 0.105 Uiso calc 1 . .
    C C12 0.8616(12) -0.0377(2) 0.8620(7) 0.0861(16) Uani d 1 . .
    H H12 1.0268 -0.0247 0.9471 0.103 Uiso calc 1 . .
    C C13 0.7476(11) -0.00665(19) 0.6908(6) 0.0715(13) Uani d 1 . .
    H H13 0.8324 0.0285 0.6645 0.086 Uiso calc 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
    Cl1 C9 . 1.743(4) ?
    S1 O1 . 1.424(3) ?
    S1 O2 . 1.424(2) ?
    S1 N1 . 1.632(3) ?
    S1 C1 . 1.770(3) ?
    O3 N3 . 1.214(4) ?
    O4 N3 . 1.204(4) ?
    N1 N2 . 1.404(4) ?
    N1 H1N . 0.86(2) ?
    N2 C7 . 1.269(5) ?
    N3 C4 . 1.481(5) ?
    C1 C6 . 1.379(5) ?
    C1 C2 . 1.391(5) ?
    C2 C3 . 1.375(5) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.367(5) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.379(5) ?
    C5 C6 . 1.378(5) ?
    C5 H5 . 0.9300 ?
    C6 H6 . 0.9300 ?
    C7 C8 . 1.468(5) ?
    C7 H7 . 0.9300 ?
    C8 C13 . 1.390(6) ?
    C8 C9 . 1.393(5) ?
    C9 C10 . 1.373(6) ?
    C10 C11 . 1.370(7) ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.380(7) ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.378(6) ?
    C12 H12 . 0.9300 ?
    C13 H13 . 0.9300 ?
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
    O1 S1 O2 . . 120.09(15) ?
    O1 S1 N1 . . 107.89(16) ?
    O2 S1 N1 . . 104.77(15) ?
    O1 S1 C1 . . 107.59(16) ?
    O2 S1 C1 . . 109.75(16) ?
    N1 S1 C1 . . 105.87(15) ?
    N2 N1 S1 . . 113.8(2) ?
    N2 N1 H1N . . 115(3) ?
    S1 N1 H1N . . 114(3) ?
    C7 N2 N1 . . 115.4(3) ?
    O4 N3 O3 . . 123.9(4) ?
    O4 N3 C4 . . 117.3(4) ?
    O3 N3 C4 . . 118.8(4) ?
    C6 C1 C2 . . 121.4(3) ?
    C6 C1 S1 . . 119.4(3) ?
    C2 C1 S1 . . 119.0(3) ?
    C3 C2 C1 . . 119.4(3) ?
    C3 C2 H2 . . 120.3 ?
    C1 C2 H2 . . 120.3 ?
    C4 C3 C2 . . 118.3(3) ?
    C4 C3 H3 . . 120.8 ?
    C2 C3 H3 . . 120.8 ?
    C3 C4 C5 . . 123.1(3) ?
    C3 C4 N3 . . 118.2(3) ?
    C5 C4 N3 . . 118.7(3) ?
    C6 C5 C4 . . 118.6(3) ?
    C6 C5 H5 . . 120.7 ?
    C4 C5 H5 . . 120.7 ?
    C1 C6 C5 . . 119.1(3) ?
    C1 C6 H6 . . 120.5 ?
    C5 C6 H6 . . 120.5 ?
    N2 C7 C8 . . 119.2(3) ?
    N2 C7 H7 . . 120.4 ?
    C8 C7 H7 . . 120.4 ?
    C13 C8 C9 . . 117.3(3) ?
    C13 C8 C7 . . 120.9(4) ?
    C9 C8 C7 . . 121.8(3) ?
    C10 C9 C8 . . 121.8(4) ?
    C10 C9 Cl1 . . 117.7(3) ?
    C8 C9 Cl1 . . 120.5(3) ?
    C11 C10 C9 . . 119.4(4) ?
    C11 C10 H10 . . 120.3 ?
    C9 C10 H10 . . 120.3 ?
    C10 C11 C12 . . 120.7(4) ?
    C10 C11 H11 . . 119.7 ?
    C12 C11 H11 . . 119.7 ?
    C11 C12 C13 . . 119.3(5) ?
    C11 C12 H12 . . 120.3 ?
    C13 C12 H12 . . 120.3 ?
    C12 C13 C8 . . 121.4(4) ?
    C12 C13 H13 . . 119.3 ?
    C8 C13 H13 . . 119.3 ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    O1 S1 N1 N2 . . . . 56.0(3) ?
    O2 S1 N1 N2 . . . . -175.0(2) ?
    C1 S1 N1 N2 . . . . -59.0(3) ?
    S1 N1 N2 C7 . . . . 159.3(3) ?
    O1 S1 C1 C6 . . . . 151.0(3) ?
    O2 S1 C1 C6 . . . . 18.7(3) ?
    N1 S1 C1 C6 . . . . -93.9(3) ?
    O1 S1 C1 C2 . . . . -32.1(3) ?
    O2 S1 C1 C2 . . . . -164.4(3) ?
    N1 S1 C1 C2 . . . . 83.0(3) ?
    C6 C1 C2 C3 . . . . 1.7(5) ?
    S1 C1 C2 C3 . . . . -175.1(3) ?
    C1 C2 C3 C4 . . . . -0.4(5) ?
    C2 C3 C4 C5 . . . . -0.7(6) ?
    C2 C3 C4 N3 . . . . 178.0(3) ?
    O4 N3 C4 C3 . . . . -170.0(4) ?
    O3 N3 C4 C3 . . . . 8.2(5) ?
    O4 N3 C4 C5 . . . . 8.7(6) ?
    O3 N3 C4 C5 . . . . -173.0(4) ?
    C3 C4 C5 C6 . . . . 0.5(6) ?
    N3 C4 C5 C6 . . . . -178.2(3) ?
    C2 C1 C6 C5 . . . . -1.9(5) ?
    S1 C1 C6 C5 . . . . 174.9(3) ?
    C4 C5 C6 C1 . . . . 0.8(5) ?
    N1 N2 C7 C8 . . . . -179.1(3) ?
    N2 C7 C8 C13 . . . . 22.2(5) ?
    N2 C7 C8 C9 . . . . -158.0(4) ?
    C13 C8 C9 C10 . . . . 0.2(6) ?
    C7 C8 C9 C10 . . . . -179.6(4) ?
    C13 C8 C9 Cl1 . . . . -177.9(3) ?
    C7 C8 C9 Cl1 . . . . 2.3(5) ?
    C8 C9 C10 C11 . . . . -1.1(7) ?
    Cl1 C9 C10 C11 . . . . 177.1(4) ?
    C9 C10 C11 C12 . . . . -0.2(8) ?
    C10 C11 C12 C13 . . . . 2.3(9) ?
    C11 C12 C13 C8 . . . . -3.2(9) ?
    C9 C8 C13 C12 . . . . 2.0(7) ?
    C7 C8 C13 C12 . . . . -178.2(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
    N1 H1N O1 1_455 0.86(2) 2.02(3) 2.853(4) 163(4)
    C3 H3 O2 1_656 0.93 2.46 3.290(4) 149
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_T_min     0.907
_shelx_estimated_absorpt_T_max     0.952
_shelxl_version_number     2014/6
data_II
_audit_creation_method     SHELXL-2014/6
_chemical_name_systematic
;
(E)-N'-(2-Methylbenzylidene)-4-nitrobenzenesulfonohydrazide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H13 N3 O4 S'
_chemical_formula_sum     'C14 H13 N3 O4 S'
_chemical_formula_iupac     'C14 H13 N3 O4 S'
_chemical_formula_weight     319.33
_chemical_melting_point     ?
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21/c'
_space_group_name_Hall     '-P 2ybc'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     7.1900(10)
_cell_length_b     15.288(2)
_cell_length_c     13.596(2)
_cell_angle_alpha     90
_cell_angle_beta     97.68(2)
_cell_angle_gamma     90
_cell_volume     1481.1(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2833
_cell_measurement_theta_min     2.64
_cell_measurement_theta_max     27.81
_cell_measurement_temperature     293(2)
_exptl_crystal_description     rod
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.500
_exptl_crystal_size_mid     0.480
_exptl_crystal_size_min     0.240
_exptl_crystal_density_diffrn     1.432
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     664
_exptl_absorpt_coefficient_mu     0.240
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2009)
;
_exptl_absorpt_correction_T_min     0.889
_exptl_absorpt_correction_T_max     0.945
_diffrn_ambient_temperature     293(2)
_diffrn_source     'Enhance (Mo) X-ray Source'
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur single crystal X-ray diffractometer
with Sapphire CCD detector
;
_diffrn_measurement_method
;
Rotation method data acquisition using omega scans.
;
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     9810
_diffrn_reflns_av_R_equivalents     0.0203
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_theta_min     2.665
_diffrn_reflns_theta_max     25.350
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     5
_diffrn_reflns_limit_k_min     -18
_diffrn_reflns_limit_k_max     18
_diffrn_reflns_limit_l_min     -11
_diffrn_reflns_limit_l_max     16
_refine_special_details     ?
_reflns_number_total     2719
_reflns_number_gt     2271
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0480
_refine_ls_R_factor_gt     0.0383
_refine_ls_wR_factor_gt     0.0911
_refine_ls_wR_factor_ref     0.0966
_refine_ls_goodness_of_fit_ref     1.045
_refine_ls_restrained_S_all     1.046
_refine_ls_number_reflns     2719
_refine_ls_number_parameters     203
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0372P)²+0.8005P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.280
_refine_diff_density_min     -0.318
_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
;
CrysAlis CCD (Oxford Diffraction, 2009)
;
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_structure_solution
;
SHELXS2013 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015)
;
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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.1811(3) 0.53913(12) 0.11782(14) 0.0392(4) Uani d 1 . .
    C C2 0.2549(3) 0.45557(13) 0.12179(16) 0.0472(5) Uani d 1 . .
    H H2 0.3779 0.4459 0.1104 0.057 Uiso calc 1 . .
    C C3 0.1428(3) 0.38663(13) 0.14295(16) 0.0515(5) Uani d 1 . .
    H H3 0.1894 0.3298 0.1470 0.062 Uiso calc 1 . .
    C C4 -0.0386(3) 0.40354(13) 0.15791(14) 0.0458(5) Uani d 1 . .
    C C5 -0.1143(3) 0.48574(14) 0.15301(16) 0.0506(5) Uani d 1 . .
    H H5 -0.2384 0.4948 0.1628 0.061 Uiso calc 1 . .
    C C6 -0.0019(3) 0.55474(13) 0.13323(16) 0.0475(5) Uani d 1 . .
    H H6 -0.0489 0.6115 0.1303 0.057 Uiso calc 1 . .
    C C7 0.5612(3) 0.62282(12) 0.35371(15) 0.0414(4) Uani d 1 . .
    H H7 0.5251 0.6771 0.3756 0.050 Uiso calc 1 . .
    C C8 0.6602(3) 0.56164(13) 0.42534(15) 0.0419(5) Uani d 1 . .
    C C9 0.7375(3) 0.58901(15) 0.52053(16) 0.0513(5) Uani d 1 . .
    C C10 0.8215(3) 0.52648(19) 0.58632(19) 0.0651(7) Uani d 1 . .
    H H10 0.8717 0.5436 0.6500 0.078 Uiso calc 1 . .
    C C11 0.8321(3) 0.4407(2) 0.5599(2) 0.0701(8) Uani d 1 . .
    H H11 0.8900 0.4004 0.6053 0.084 Uiso calc 1 . .
    C C12 0.7574(3) 0.41387(16) 0.4665(2) 0.0651(7) Uani d 1 . .
    H H12 0.7657 0.3555 0.4483 0.078 Uiso calc 1 . .
    C C13 0.6700(3) 0.47378(14) 0.39960(18) 0.0513(5) Uani d 1 . .
    H H13 0.6172 0.4553 0.3369 0.062 Uiso calc 1 . .
    C C14 0.7337(4) 0.68279(18) 0.5534(2) 0.0781(8) Uani d 1 . .
    H H14A 0.6070 0.7041 0.5427 0.117 Uiso calc 1 . .
    H H14B 0.8104 0.7174 0.5157 0.117 Uiso calc 1 . .
    H H14C 0.7813 0.6868 0.6226 0.117 Uiso calc 1 . .
    N N1 0.4195(2) 0.66562(10) 0.20225(12) 0.0431(4) Uani d 1 . .
    H H1N 0.347(3) 0.6988(13) 0.2284(16) 0.052 Uiso d 1 . .
    N N2 0.5234(2) 0.60339(10) 0.26201(12) 0.0413(4) Uani d 1 . .
    N N3 -0.1566(3) 0.32996(13) 0.18268(14) 0.0592(5) Uani d 1 . .
    O O1 0.2086(2) 0.69660(9) 0.05038(11) 0.0591(4) Uani d 1 . .
    O O2 0.4735(2) 0.59482(10) 0.04571(11) 0.0590(4) Uani d 1 . .
    O O3 -0.3229(3) 0.34312(13) 0.18613(15) 0.0833(6) Uani d 1 . .
    O O4 -0.0808(3) 0.25947(12) 0.19986(16) 0.0867(6) Uani d 1 . .
    S S1 0.32586(7) 0.62811(3) 0.09402(4) 0.04312(16) Uani d 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
    C1 C6 . 1.381(3) ?
    C1 C2 . 1.381(3) ?
    C1 S1 . 1.7687(19) ?
    C2 C3 . 1.380(3) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.371(3) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.368(3) ?
    C4 N3 . 1.475(3) ?
    C5 C6 . 1.377(3) ?
    C5 H5 . 0.9300 ?
    C6 H6 . 0.9300 ?
    C7 N2 . 1.275(2) ?
    C7 C8 . 1.465(3) ?
    C7 H7 . 0.9300 ?
    C8 C13 . 1.392(3) ?
    C8 C9 . 1.402(3) ?
    C9 C10 . 1.391(3) ?
    C9 C14 . 1.503(3) ?
    C10 C11 . 1.364(4) ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.375(4) ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.381(3) ?
    C12 H12 . 0.9300 ?
    C13 H13 . 0.9300 ?
    C14 H14A . 0.9600 ?
    C14 H14B . 0.9600 ?
    C14 H14C . 0.9600 ?
    N1 N2 . 1.400(2) ?
    N1 S1 . 1.6380(17) ?
    N1 H1N . 0.839(15) ?
    N3 O4 . 1.216(3) ?
    N3 O3 . 1.220(3) ?
    O1 S1 . 1.4233(15) ?
    O2 S1 . 1.4157(15) ?
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
    C6 C1 C2 . . 121.50(18) ?
    C6 C1 S1 . . 119.39(15) ?
    C2 C1 S1 . . 119.10(15) ?
    C3 C2 C1 . . 118.86(19) ?
    C3 C2 H2 . . 120.6 ?
    C1 C2 H2 . . 120.6 ?
    C4 C3 C2 . . 118.70(19) ?
    C4 C3 H3 . . 120.6 ?
    C2 C3 H3 . . 120.6 ?
    C5 C4 C3 . . 123.12(19) ?
    C5 C4 N3 . . 118.3(2) ?
    C3 C4 N3 . . 118.5(2) ?
    C4 C5 C6 . . 118.25(19) ?
    C4 C5 H5 . . 120.9 ?
    C6 C5 H5 . . 120.9 ?
    C5 C6 C1 . . 119.56(19) ?
    C5 C6 H6 . . 120.2 ?
    C1 C6 H6 . . 120.2 ?
    N2 C7 C8 . . 121.51(18) ?
    N2 C7 H7 . . 119.2 ?
    C8 C7 H7 . . 119.2 ?
    C13 C8 C9 . . 119.5(2) ?
    C13 C8 C7 . . 119.03(19) ?
    C9 C8 C7 . . 121.37(19) ?
    C10 C9 C8 . . 118.2(2) ?
    C10 C9 C14 . . 119.2(2) ?
    C8 C9 C14 . . 122.5(2) ?
    C11 C10 C9 . . 121.8(2) ?
    C11 C10 H10 . . 119.1 ?
    C9 C10 H10 . . 119.1 ?
    C10 C11 C12 . . 120.1(2) ?
    C10 C11 H11 . . 120.0 ?
    C12 C11 H11 . . 120.0 ?
    C11 C12 C13 . . 119.8(2) ?
    C11 C12 H12 . . 120.1 ?
    C13 C12 H12 . . 120.1 ?
    C12 C13 C8 . . 120.5(2) ?
    C12 C13 H13 . . 119.7 ?
    C8 C13 H13 . . 119.7 ?
    C9 C14 H14A . . 109.5 ?
    C9 C14 H14B . . 109.5 ?
    H14A C14 H14B . . 109.5 ?
    C9 C14 H14C . . 109.5 ?
    H14A C14 H14C . . 109.5 ?
    H14B C14 H14C . . 109.5 ?
    N2 N1 S1 . . 114.00(12) ?
    N2 N1 H1N . . 118.6(15) ?
    S1 N1 H1N . . 112.8(15) ?
    C7 N2 N1 . . 115.88(16) ?
    O4 N3 O3 . . 123.7(2) ?
    O4 N3 C4 . . 117.6(2) ?
    O3 N3 C4 . . 118.7(2) ?
    O2 S1 O1 . . 120.69(10) ?
    O2 S1 N1 . . 107.39(9) ?
    O1 S1 N1 . . 105.46(9) ?
    O2 S1 C1 . . 107.72(9) ?
    O1 S1 C1 . . 108.17(9) ?
    N1 S1 C1 . . 106.63(9) ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C6 C1 C2 C3 . . . . -0.9(3) ?
    S1 C1 C2 C3 . . . . 178.33(16) ?
    C1 C2 C3 C4 . . . . 0.9(3) ?
    C2 C3 C4 C5 . . . . -0.1(3) ?
    C2 C3 C4 N3 . . . . -178.67(19) ?
    C3 C4 C5 C6 . . . . -0.8(3) ?
    N3 C4 C5 C6 . . . . 177.81(19) ?
    C4 C5 C6 C1 . . . . 0.8(3) ?
    C2 C1 C6 C5 . . . . 0.0(3) ?
    S1 C1 C6 C5 . . . . -179.19(16) ?
    N2 C7 C8 C13 . . . . -17.0(3) ?
    N2 C7 C8 C9 . . . . 165.96(18) ?
    C13 C8 C9 C10 . . . . -0.1(3) ?
    C7 C8 C9 C10 . . . . 176.89(18) ?
    C13 C8 C9 C14 . . . . 179.5(2) ?
    C7 C8 C9 C14 . . . . -3.5(3) ?
    C8 C9 C10 C11 . . . . 0.9(3) ?
    C14 C9 C10 C11 . . . . -178.7(2) ?
    C9 C10 C11 C12 . . . . -0.5(4) ?
    C10 C11 C12 C13 . . . . -0.6(3) ?
    C11 C12 C13 C8 . . . . 1.3(3) ?
    C9 C8 C13 C12 . . . . -1.0(3) ?
    C7 C8 C13 C12 . . . . -178.05(19) ?
    C8 C7 N2 N1 . . . . 176.70(15) ?
    S1 N1 N2 C7 . . . . -164.16(14) ?
    C5 C4 N3 O4 . . . . -170.4(2) ?
    C3 C4 N3 O4 . . . . 8.3(3) ?
    C5 C4 N3 O3 . . . . 8.7(3) ?
    C3 C4 N3 O3 . . . . -172.7(2) ?
    N2 N1 S1 O2 . . . . -57.23(15) ?
    N2 N1 S1 O1 . . . . 172.86(13) ?
    N2 N1 S1 C1 . . . . 58.01(15) ?
    C6 C1 S1 O2 . . . . -158.52(16) ?
    C2 C1 S1 O2 . . . . 22.28(19) ?
    C6 C1 S1 O1 . . . . -26.54(19) ?
    C2 C1 S1 O1 . . . . 154.26(16) ?
    C6 C1 S1 N1 . . . . 86.46(17) ?
    C2 C1 S1 N1 . . . . -92.74(17) ?
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 H1N O3 2 0.839(15) 2.511(18) 3.230(2) 144.3(19)
    N1 H1N O4 2 0.839(15) 2.444(16) 3.260(3) 164(2)
    C2 H2 O2 3_665 0.93 2.58 3.284(2) 133
    C12 H12 O1 2_645 0.93 2.44 3.341(3) 164
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_T_min     0.889
_shelx_estimated_absorpt_T_max     0.945
_shelxl_version_number     2014/6
data_III
_audit_creation_method     SHELXL-2014/6
_chemical_name_systematic
;
(E)-N'-(4-Methylbenzylidene)-4-nitrobenzenesulfonohydrazide
monohydrate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H13 N3 O4 S, H2 O'
_chemical_formula_sum     'C14 H15 N3 O5 S'
_chemical_formula_iupac     'C14 H13 N3 O4 S, H2 O'
_chemical_formula_weight     337.35
_chemical_melting_point     ?
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21/c'
_space_group_name_Hall     '-P 2ybc'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     22.589(2)
_cell_length_b     5.4424(4)
_cell_length_c     12.7180(9)
_cell_angle_alpha     90
_cell_angle_beta     92.146(6)
_cell_angle_gamma     90
_cell_volume     1562.4(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3331
_cell_measurement_theta_min     3.09
_cell_measurement_theta_max     27.77
_cell_measurement_temperature     293(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.400
_exptl_crystal_size_mid     0.360
_exptl_crystal_size_min     0.160
_exptl_crystal_density_diffrn     1.434
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     704
_exptl_absorpt_coefficient_mu     0.236
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2009)
;
_exptl_absorpt_correction_T_min     0.911
_exptl_absorpt_correction_T_max     0.963
_diffrn_ambient_temperature     293(2)
_diffrn_source     'Enhance (Mo) X-ray Source'
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur single crystal X-ray diffractometer
with Sapphire CCD detector
;
_diffrn_measurement_method
;
Rotation method data acquisition using omega scans.
;
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     9384
_diffrn_reflns_av_R_equivalents     0.0213
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_theta_min     3.206
_diffrn_reflns_theta_max     25.350
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -19
_diffrn_reflns_limit_h_max     27
_diffrn_reflns_limit_k_min     -6
_diffrn_reflns_limit_k_max     6
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     15
_refine_special_details     ?
_reflns_number_total     2870
_reflns_number_gt     2178
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0524
_refine_ls_R_factor_gt     0.0343
_refine_ls_wR_factor_gt     0.0838
_refine_ls_wR_factor_ref     0.0916
_refine_ls_goodness_of_fit_ref     1.020
_refine_ls_restrained_S_all     1.021
_refine_ls_number_reflns     2870
_refine_ls_number_parameters     218
_refine_ls_number_restraints     6
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0464P)²+0.3615P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_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     0.193
_refine_diff_density_min     -0.277
_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
;
CrysAlis CCD (Oxford Diffraction, 2009)
;
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_structure_solution
;
SHELXS2013 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015)
;
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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.29814(2) -0.41337(9) 0.00460(3) 0.04151(15) Uani d 1 . .
    O O1 0.31514(6) -0.4922(3) -0.09707(10) 0.0540(4) Uani d 1 . .
    O O2 0.28665(6) -0.5896(2) 0.08395(10) 0.0533(4) Uani d 1 . .
    O O3 0.50400(7) 0.4229(3) 0.11440(12) 0.0697(5) Uani d 1 . .
    O O4 0.45497(7) 0.4367(3) 0.25661(11) 0.0619(4) Uani d 1 . .
    N N1 0.23739(7) -0.2563(3) -0.01813(12) 0.0465(4) Uani d 1 . .
    H H1N 0.2396(9) -0.153(3) -0.0681(14) 0.056 Uiso d 1 . .
    N N2 0.21027(7) -0.1771(3) 0.07293(12) 0.0470(4) Uani d 1 . .
    N N3 0.46427(7) 0.3533(3) 0.16974(13) 0.0463(4) Uani d 1 . .
    C C1 0.35122(7) -0.2010(3) 0.05425(13) 0.0367(4) Uani d 1 . .
    C C2 0.38690(8) -0.0791(4) -0.01472(14) 0.0439(4) Uani d 1 . .
    H H2 0.3852 -0.1181 -0.0860 0.053 Uiso calc 1 . .
    C C3 0.42513(8) 0.1012(4) 0.02325(14) 0.0440(4) Uani d 1 . .
    H H3 0.4500 0.1839 -0.0215 0.053 Uiso calc 1 . .
    C C4 0.42543(7) 0.1550(3) 0.12892(14) 0.0383(4) Uani d 1 . .
    C C5 0.39051(8) 0.0344(4) 0.19866(14) 0.0431(4) Uani d 1 . .
    H H5 0.3923 0.0746 0.2698 0.052 Uiso calc 1 . .
    C C6 0.35286(8) -0.1470(3) 0.16104(13) 0.0424(4) Uani d 1 . .
    H H6 0.3289 -0.2321 0.2065 0.051 Uiso calc 1 . .
    C C7 0.17972(8) 0.0167(4) 0.06417(16) 0.0505(5) Uani d 1 . .
    H H7 0.1791 0.1035 0.0012 0.061 Uiso calc 1 . .
    C C8 0.14529(8) 0.1070(4) 0.15155(16) 0.0501(5) Uani d 1 . .
    C C9 0.11387(10) 0.3238(4) 0.14097(19) 0.0669(6) Uani d 1 . .
    H H9 0.1164 0.4165 0.0799 0.080 Uiso calc 1 . .
    C C10 0.07863(11) 0.4042(5) 0.2206(2) 0.0754(7) Uani d 1 . .
    H H10 0.0578 0.5505 0.2118 0.090 Uiso calc 1 . .
    C C11 0.07354(10) 0.2750(5) 0.31180(19) 0.0670(6) Uani d 1 . .
    C C12 0.10618(11) 0.0627(5) 0.32272(19) 0.0725(7) Uani d 1 . .
    H H12 0.1044 -0.0267 0.3848 0.087 Uiso calc 1 . .
    C C13 0.14130(10) -0.0210(4) 0.24460(17) 0.0626(6) Uani d 1 . .
    H H13 0.1627 -0.1658 0.2545 0.075 Uiso calc 1 . .
    C C14 0.03449(12) 0.3685(6) 0.3974(2) 0.0970(10) Uani d 1 . .
    H H14A 0.0205 0.2322 0.4374 0.146 Uiso calc 1 . .
    H H14B 0.0013 0.4553 0.3660 0.146 Uiso calc 1 . .
    H H14C 0.0569 0.4774 0.4430 0.146 Uiso calc 1 . .
    O O5 0.25535(9) 0.4283(3) 0.31149(13) 0.0753(5) Uani d 1 . .
    H H51 0.2502(12) 0.445(5) 0.2487(14) 0.090 Uiso d 1 . .
    H H52 0.2685(12) 0.296(4) 0.328(2) 0.090 Uiso d 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 O2 . 1.4230(13) ?
    S1 O1 . 1.4284(13) ?
    S1 N1 . 1.6335(17) ?
    S1 C1 . 1.7652(18) ?
    O3 N3 . 1.221(2) ?
    O4 N3 . 1.220(2) ?
    N1 N2 . 1.398(2) ?
    N1 H1N . 0.850(15) ?
    N2 C7 . 1.263(3) ?
    N3 C4 . 1.473(2) ?
    C1 C2 . 1.383(2) ?
    C1 C6 . 1.389(2) ?
    C2 C3 . 1.382(3) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.375(2) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.375(2) ?
    C5 C6 . 1.377(3) ?
    C5 H5 . 0.9300 ?
    C6 H6 . 0.9300 ?
    C7 C8 . 1.465(3) ?
    C7 H7 . 0.9300 ?
    C8 C13 . 1.379(3) ?
    C8 C9 . 1.381(3) ?
    C9 C10 . 1.383(3) ?
    C9 H9 . 0.9300 ?
    C10 C11 . 1.365(3) ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.375(3) ?
    C11 C14 . 1.514(3) ?
    C12 C13 . 1.372(3) ?
    C12 H12 . 0.9300 ?
    C13 H13 . 0.9300 ?
    C14 H14A . 0.9600 ?
    C14 H14B . 0.9600 ?
    C14 H14C . 0.9600 ?
    O5 H51 . 0.808(16) ?
    O5 H52 . 0.802(17) ?
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
    O2 S1 O1 . . 120.13(8) ?
    O2 S1 N1 . . 107.70(8) ?
    O1 S1 N1 . . 104.45(8) ?
    O2 S1 C1 . . 109.10(8) ?
    O1 S1 C1 . . 108.56(8) ?
    N1 S1 C1 . . 105.98(8) ?
    N2 N1 S1 . . 113.94(12) ?
    N2 N1 H1N . . 117.2(14) ?
    S1 N1 H1N . . 113.8(15) ?
    C7 N2 N1 . . 116.04(17) ?
    O4 N3 O3 . . 124.16(17) ?
    O4 N3 C4 . . 118.13(15) ?
    O3 N3 C4 . . 117.71(16) ?
    C2 C1 C6 . . 121.61(17) ?
    C2 C1 S1 . . 119.44(13) ?
    C6 C1 S1 . . 118.77(13) ?
    C3 C2 C1 . . 119.35(16) ?
    C3 C2 H2 . . 120.3 ?
    C1 C2 H2 . . 120.3 ?
    C4 C3 C2 . . 118.22(16) ?
    C4 C3 H3 . . 120.9 ?
    C2 C3 H3 . . 120.9 ?
    C3 C4 C5 . . 123.13(17) ?
    C3 C4 N3 . . 118.79(15) ?
    C5 C4 N3 . . 118.07(16) ?
    C4 C5 C6 . . 118.66(16) ?
    C4 C5 H5 . . 120.7 ?
    C6 C5 H5 . . 120.7 ?
    C5 C6 C1 . . 119.01(16) ?
    C5 C6 H6 . . 120.5 ?
    C1 C6 H6 . . 120.5 ?
    N2 C7 C8 . . 121.14(19) ?
    N2 C7 H7 . . 119.4 ?
    C8 C7 H7 . . 119.4 ?
    C13 C8 C9 . . 117.7(2) ?
    C13 C8 C7 . . 122.4(2) ?
    C9 C8 C7 . . 119.9(2) ?
    C8 C9 C10 . . 120.4(2) ?
    C8 C9 H9 . . 119.8 ?
    C10 C9 H9 . . 119.8 ?
    C11 C10 C9 . . 121.9(2) ?
    C11 C10 H10 . . 119.0 ?
    C9 C10 H10 . . 119.0 ?
    C10 C11 C12 . . 117.2(2) ?
    C10 C11 C14 . . 120.5(2) ?
    C12 C11 C14 . . 122.3(3) ?
    C13 C12 C11 . . 121.9(2) ?
    C13 C12 H12 . . 119.1 ?
    C11 C12 H12 . . 119.1 ?
    C12 C13 C8 . . 120.8(2) ?
    C12 C13 H13 . . 119.6 ?
    C8 C13 H13 . . 119.6 ?
    C11 C14 H14A . . 109.5 ?
    C11 C14 H14B . . 109.5 ?
    H14A C14 H14B . . 109.5 ?
    C11 C14 H14C . . 109.5 ?
    H14A C14 H14C . . 109.5 ?
    H14B C14 H14C . . 109.5 ?
    H51 O5 H52 . . 113(3) ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    O2 S1 N1 N2 . . . . 46.42(15) ?
    O1 S1 N1 N2 . . . . 175.19(13) ?
    C1 S1 N1 N2 . . . . -70.24(14) ?
    S1 N1 N2 C7 . . . . 152.32(14) ?
    O2 S1 C1 C2 . . . . 153.79(14) ?
    O1 S1 C1 C2 . . . . 21.22(17) ?
    N1 S1 C1 C2 . . . . -90.50(15) ?
    O2 S1 C1 C6 . . . . -31.06(16) ?
    O1 S1 C1 C6 . . . . -163.64(14) ?
    N1 S1 C1 C6 . . . . 84.65(15) ?
    C6 C1 C2 C3 . . . . -0.1(3) ?
    S1 C1 C2 C3 . . . . 174.89(14) ?
    C1 C2 C3 C4 . . . . -1.0(3) ?
    C2 C3 C4 C5 . . . . 1.4(3) ?
    C2 C3 C4 N3 . . . . -177.66(16) ?
    O4 N3 C4 C3 . . . . 163.87(17) ?
    O3 N3 C4 C3 . . . . -16.5(2) ?
    O4 N3 C4 C5 . . . . -15.3(2) ?
    O3 N3 C4 C5 . . . . 164.39(17) ?
    C3 C4 C5 C6 . . . . -0.8(3) ?
    N3 C4 C5 C6 . . . . 178.33(16) ?
    C4 C5 C6 C1 . . . . -0.3(3) ?
    C2 C1 C6 C5 . . . . 0.8(3) ?
    S1 C1 C6 C5 . . . . -174.26(14) ?
    N1 N2 C7 C8 . . . . 175.00(16) ?
    N2 C7 C8 C13 . . . . -4.2(3) ?
    N2 C7 C8 C9 . . . . 177.82(19) ?
    C13 C8 C9 C10 . . . . -1.6(3) ?
    C7 C8 C9 C10 . . . . 176.5(2) ?
    C8 C9 C10 C11 . . . . 0.2(4) ?
    C9 C10 C11 C12 . . . . 1.5(4) ?
    C9 C10 C11 C14 . . . . -180.0(2) ?
    C10 C11 C12 C13 . . . . -1.7(4) ?
    C14 C11 C12 C13 . . . . 179.8(2) ?
    C11 C12 C13 C8 . . . . 0.3(4) ?
    C9 C8 C13 C12 . . . . 1.4(3) ?
    C7 C8 C13 C12 . . . . -176.6(2) ?
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 H1N O5 4_565 0.850(15) 2.003(15) 2.848(2) 173(2)
    O5 H51 O2 1_565 0.808(16) 2.29(2) 3.006(2) 148(3)
    O5 H52 O1 4_556 0.802(17) 2.165(18) 2.949(2) 166(3)
    C5 H5 O1 4_556 0.93 2.52 3.167(2) 127
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_T_min     0.911
_shelx_estimated_absorpt_T_max     0.963
_shelxl_version_number     2014/6
data_global
_journal_date_recd_electronic     2018-10-23
_journal_date_accepted     2018-10-28
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2018
_journal_volume     74
_journal_issue     12
_journal_page_first     1710
_journal_page_last     1716
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989018015207
_journal_coeditor_code     SU5460
_publ_contact_author_name     ' B. Thimme Gowda '
_publ_contact_author_address
;
Department of Chemistry, Mangalore University, Mangalagangotri-574199,
India.
;
_publ_contact_author_email     'gowdabt@yahoo.com'
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
Crystal structures and the Hirshfeld surface analysis of
(E)-4-nitro-N'-(o-chloro, o- and
p-methylbenzylidene)benzenesulfonohydrazides
;
_publ_section_title_footnote     .
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Salian, Akshatha R.' .
;
Department of Chemistry, Mangalore University, Mangalagangotri-574 199,
India
;
    'Foro, Sabine' .
;
Institute of Materials Science, Darmstadt University of Technology,
Alarich-Weiss-Str. 2, D-64287, Darmstadt, Germany
;
    'Gowda, B. Thimme' .
;
Department of Chemistry, Mangalore University, Mangalagangotri-574 199,
India
Karnataka State Rural Development and Panchayat Raj University,
Raitha Bhavan, Gadag-582101, India
;
_publ_section_synopsis
;
The crystal structures of three
N'-(arylidene)4-nitrobenzenesulfonohydrazides, namely,
(E)-4-nitro-N'-(2-chlorobenzylidene)benzenesulfonohydrazide (I),
(E)-4-nitro-N'-(2-methylbenzylidene) benzenesulfonohydrazide
(II) and
(E)-4-nitro-N'-(4-methylbenzylidene)benzenesulfonohydrazide
(III), have been studied to investigate the effect of the nature and site of
substitutions on the structural parameters and the supramolecular features in
these compounds. Hirshfeld surface analysis was also carried out to examine
the contributions of the various atom--atom interactions in the crystal
packing of the three compounds.
;
