# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1444297'
_audit_update_record             
;
2015-12-25 deposited with the CCDC.	2019-05-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
N'-[(E)-(2-nitrophenyl)methylidene]benzenesulfonohydrazide
_chemical_name_common            
N'-[(E)-(2-nitrophenyl)methylidene]benzenesulfonohydrazide
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H11 N3 O4 S'
_chemical_formula_sum            'C13 H11 N3 O4 S'
_chemical_formula_weight         305.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.5720(3)
_cell_length_b                   23.2361(9)
_cell_length_c                   10.6070(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.807(4)
_cell_angle_gamma                90
_cell_volume                     1357.11(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2586
_cell_measurement_theta_min      3.2637
_cell_measurement_theta_max      29.2394

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    0.259
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.85505
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'SADABS (Sheldrick, 96)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas, CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6309
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.270
_diffrn_reflns_theta_max         29.302
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.861
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.861
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.861
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3211
_reflns_number_gt                2411
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis PRO (Agilent, 2012)'
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2012)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0448P)²+0.4319P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3211
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.1106
_refine_ls_wR_factor_gt          0.0973
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1456(3) -0.03925(8) 0.19316(17) 0.0318(4) Uani 1 1 d . . . . .
C2 C -0.0457(4) -0.07872(8) 0.18544(18) 0.0348(4) Uani 1 1 d . . . . .
C3 C -0.1171(4) -0.11204(10) 0.0772(2) 0.0469(5) Uani 1 1 d . . . . .
H3 H -0.2441 -0.1382 0.0753 0.056 Uiso 1 1 calc R U . . .
C4 C 0.0007(4) -0.10618(10) -0.0269(2) 0.0510(6) Uani 1 1 d . . . . .
H4 H -0.0490 -0.1275 -0.1005 0.061 Uiso 1 1 calc R U . . .
C5 C 0.1932(4) -0.06847(10) -0.0215(2) 0.0482(6) Uani 1 1 d . . . . .
H5 H 0.2752 -0.0647 -0.0911 0.058 Uiso 1 1 calc R U . . .
C6 C 0.2641(4) -0.03636(9) 0.08679(19) 0.0415(5) Uani 1 1 d . . . . .
H6 H 0.3964 -0.0118 0.0891 0.050 Uiso 1 1 calc R U . . .
C7 C 0.2344(3) -0.00408(8) 0.30566(17) 0.0324(4) Uani 1 1 d . . . . .
H7 H 0.1758 -0.0099 0.3822 0.039 Uiso 1 1 calc R U . . .
C8 C 0.4929(3) 0.17465(8) 0.33649(18) 0.0336(4) Uani 1 1 d . . . . .
C9 C 0.5340(5) 0.19807(11) 0.2227(2) 0.0597(7) Uani 1 1 d . . . . .
H9 H 0.6491 0.1820 0.1783 0.072 Uiso 1 1 calc R U . . .
C10 C 0.4017(6) 0.24582(12) 0.1751(3) 0.0756(9) Uani 1 1 d . . . . .
H10 H 0.4289 0.2621 0.0984 0.091 Uiso 1 1 calc R U . . .
C11 C 0.2335(5) 0.26902(11) 0.2390(3) 0.0667(7) Uani 1 1 d . . . . .
H11 H 0.1480 0.3016 0.2071 0.080 Uiso 1 1 calc R U . . .
C12 C 0.1888(5) 0.24484(13) 0.3500(3) 0.0771(9) Uani 1 1 d . . . . .
H12 H 0.0694 0.2604 0.3923 0.092 Uiso 1 1 calc R U . . .
C13 C 0.3189(5) 0.19755(11) 0.4002(2) 0.0600(7) Uani 1 1 d . . . . .
H13 H 0.2891 0.1813 0.4764 0.072 Uiso 1 1 calc R U . . .
N1 N -0.1841(3) -0.08718(8) 0.29082(17) 0.0424(4) Uani 1 1 d . . . . .
N2 N 0.3931(3) 0.03453(7) 0.29658(14) 0.0335(4) Uani 1 1 d . . . . .
N3 N 0.4823(3) 0.06189(7) 0.40976(15) 0.0356(4) Uani 1 1 d . . . . .
O1 O -0.2863(4) -0.13333(8) 0.29722(18) 0.0756(6) Uani 1 1 d . . . . .
O2 O -0.1931(3) -0.04872(7) 0.36826(15) 0.0523(4) Uani 1 1 d . . . . .
O3 O 0.8355(3) 0.10090(6) 0.32067(14) 0.0449(4) Uani 1 1 d . . . . .
O4 O 0.7501(3) 0.12874(6) 0.53473(13) 0.0448(4) Uani 1 1 d . . . . .
S1 S 0.66702(9) 0.11604(2) 0.40335(4) 0.03306(15) Uani 1 1 d . . . . .
H1 H 0.401(4) 0.0621(9) 0.469(2) 0.040 Uiso 1 1 d . U . . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.393(3) . ?
C1 C2 1.399(3) . ?
C1 C7 1.468(3) . ?
C2 C3 1.391(3) . ?
C2 N1 1.465(3) . ?
C3 C4 1.375(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.379(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.376(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N2 1.274(2) . ?
C7 H7 0.9300 . ?
C8 C13 1.371(3) . ?
C8 C9 1.375(3) . ?
C8 S1 1.7573(19) . ?
C9 C10 1.384(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.350(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.361(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.378(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
N1 O2 1.220(2) . ?
N1 O1 1.221(2) . ?
N2 N3 1.382(2) . ?
N3 S1 1.6336(17) . ?
N3 H1 0.83(2) . ?
O3 S1 1.4234(15) . ?
O4 S1 1.4304(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 115.81(17) . . ?
C6 C1 C7 119.27(17) . . ?
C2 C1 C7 124.84(17) . . ?
C3 C2 C1 122.16(18) . . ?
C3 C2 N1 115.92(18) . . ?
C1 C2 N1 121.92(17) . . ?
C4 C3 C2 119.7(2) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 119.6(2) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 120.1(2) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C1 122.6(2) . . ?
C5 C6 H6 118.7 . . ?
C1 C6 H6 118.7 . . ?
N2 C7 C1 118.81(17) . . ?
N2 C7 H7 120.6 . . ?
C1 C7 H7 120.6 . . ?
C13 C8 C9 120.29(19) . . ?
C13 C8 S1 119.36(16) . . ?
C9 C8 S1 120.34(17) . . ?
C8 C9 C10 119.1(2) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C11 C10 C9 120.6(2) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 120.2(2) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C13 120.5(3) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C8 C13 C12 119.3(2) . . ?
C8 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
O2 N1 O1 122.58(19) . . ?
O2 N1 C2 119.72(18) . . ?
O1 N1 C2 117.69(19) . . ?
C7 N2 N3 114.83(16) . . ?
N2 N3 S1 117.60(13) . . ?
N2 N3 H1 119.9(15) . . ?
S1 N3 H1 116.5(15) . . ?
O3 S1 O4 120.37(9) . . ?
O3 S1 N3 108.32(9) . . ?
O4 S1 N3 103.32(9) . . ?
O3 S1 C8 108.57(9) . . ?
O4 S1 C8 108.04(9) . . ?
N3 S1 C8 107.53(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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -1.5(3) . . . . ?
C7 C1 C2 C3 -178.14(18) . . . . ?
C6 C1 C2 N1 178.93(18) . . . . ?
C7 C1 C2 N1 2.3(3) . . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
N1 C2 C3 C4 179.0(2) . . . . ?
C2 C3 C4 C5 1.8(4) . . . . ?
C3 C4 C5 C6 -1.0(4) . . . . ?
C4 C5 C6 C1 -1.3(4) . . . . ?
C2 C1 C6 C5 2.4(3) . . . . ?
C7 C1 C6 C5 179.27(19) . . . . ?
C6 C1 C7 N2 10.6(3) . . . . ?
C2 C1 C7 N2 -172.87(18) . . . . ?
C13 C8 C9 C10 1.6(4) . . . . ?
S1 C8 C9 C10 -177.1(2) . . . . ?
C8 C9 C10 C11 -0.4(5) . . . . ?
C9 C10 C11 C12 -1.3(5) . . . . ?
C10 C11 C12 C13 1.8(5) . . . . ?
C9 C8 C13 C12 -1.1(4) . . . . ?
S1 C8 C13 C12 177.6(2) . . . . ?
C11 C12 C13 C8 -0.6(5) . . . . ?
C3 C2 N1 O2 -155.42(19) . . . . ?
C1 C2 N1 O2 24.2(3) . . . . ?
C3 C2 N1 O1 24.8(3) . . . . ?
C1 C2 N1 O1 -155.6(2) . . . . ?
C1 C7 N2 N3 -174.35(15) . . . . ?
C7 N2 N3 S1 -174.31(14) . . . . ?
N2 N3 S1 O3 -43.40(17) . . . . ?
N2 N3 S1 O4 -172.14(14) . . . . ?
N2 N3 S1 C8 73.75(16) . . . . ?
C13 C8 S1 O3 -179.19(18) . . . . ?
C9 C8 S1 O3 -0.5(2) . . . . ?
C13 C8 S1 O4 -47.1(2) . . . . ?
C9 C8 S1 O4 131.58(19) . . . . ?
C13 C8 S1 N3 63.8(2) . . . . ?
C9 C8 S1 N3 -117.50(19) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C7 H7 O2 0.93 2.23 2.770(2) 116.4 .
C13 H13 O1 0.93 2.65 3.569(3) 170.1 3_556
N3 H1 O2 0.83(2) 2.24(2) 3.065(2) 172(2) 3_556

_refine_diff_density_max         0.282
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.050


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
