# 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 2017

####################################################################### 
# 
# 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_nadeem
_database_code_depnum_ccdc_archive 'CCDC 1547641'
_audit_update_record             
;
2017-05-03 deposited with the CCDC.
2017-12-06 downloaded from the CCDC.
;
_audit_creation_date             2017-05-03
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            
;
N'-[(E)-(2-methoxyphenyl)methylidene]benzenesulfonohydrazide
;
_chemical_name_systematic        
;
N'-[(E)-(2-methoxyphenyl)methylidene]benzenesulfonohydrazide
;
_chemical_formula_moiety         'C14 H14 N2 O3 S'
_chemical_formula_sum            'C14 H14 N2 O3 S'
_chemical_formula_weight         290.33
_chemical_melting_point          ?
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.8094(5)
_cell_length_b                   11.2917(8)
_cell_length_c                   14.9528(9)
_cell_angle_alpha                73.214(5)
_cell_angle_beta                 85.325(4)
_cell_angle_gamma                83.268(5)
_cell_volume                     1412.43(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5191
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.1456
_cell_measurement_theta_min      2.9368
_exptl_absorpt_coefficient_mu    0.237
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.32
_exptl_special_details           ?
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.876
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12804
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.876
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.210
_diffrn_reflns_theta_min         2.943
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.876
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas, CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5366
_reflns_number_total             6701
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2012)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2012)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2012)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         6701
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0410
_refine_ls_restrained_S_all      0.963
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0684P)²+0.3024P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1098
_refine_ls_wR_factor_ref         0.1222
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
S1 S 0.84767(4) 0.07599(3) 0.37555(3) 0.03977(11) Uani 1 1 d . . . . .
S2 S 0.67533(4) 0.51459(4) 0.87999(3) 0.04170(12) Uani 1 1 d . . . . .
O1 O 0.90054(14) -0.04653(10) 0.43097(9) 0.0510(3) Uani 1 1 d . . . . .
O4 O 0.72649(15) 0.55873(12) 0.78489(9) 0.0564(3) Uani 1 1 d . . . . .
O2 O 0.82669(15) 0.09620(12) 0.27886(8) 0.0548(3) Uani 1 1 d . . . . .
O3 O 1.18700(14) 0.51824(12) 0.41555(9) 0.0537(3) Uani 1 1 d . . . . .
O6 O 0.32354(14) 0.04733(13) 0.91183(10) 0.0599(3) Uani 1 1 d . . . . .
N1 N 0.93269(15) 0.28988(12) 0.35219(9) 0.0411(3) Uani 1 1 d . . . . .
O5 O 0.60479(15) 0.60166(11) 0.92794(10) 0.0561(3) Uani 1 1 d . . . . .
N2 N 0.97980(15) 0.16253(12) 0.38519(10) 0.0423(3) Uani 1 1 d D . . . .
N3 N 0.59207(15) 0.31968(13) 0.85257(10) 0.0437(3) Uani 1 1 d . . . . .
N4 N 0.54161(16) 0.42121(14) 0.88666(11) 0.0472(3) Uani 1 1 d D . . . .
C7 C 1.00163(17) 0.36008(14) 0.38422(11) 0.0387(3) Uani 1 1 d . . . . .
H7 H 1.080109 0.326258 0.424812 0.046 Uiso 1 1 calc R U . . .
C16 C 0.56228(17) 0.11403(15) 0.85279(11) 0.0401(3) Uani 1 1 d . . . . .
C17 C 0.46005(19) 0.02333(15) 0.86746(11) 0.0439(4) Uani 1 1 d . . . . .
C1 C 0.95800(17) 0.49422(14) 0.35747(11) 0.0395(3) Uani 1 1 d . . . . .
C23 C 0.82649(17) 0.42211(14) 0.94376(11) 0.0393(3) Uani 1 1 d . . . . .
C8 C 0.67769(17) 0.13075(14) 0.42711(11) 0.0376(3) Uani 1 1 d . . . . .
C22 C 0.51886(17) 0.22483(15) 0.88454(12) 0.0422(3) Uani 1 1 d . . . . .
H22 H 0.437544 0.225727 0.928181 0.051 Uiso 1 1 calc R U . . .
C2 C 1.05503(19) 0.57414(15) 0.37462(11) 0.0420(3) Uani 1 1 d . . . . .
C11 C 0.4191(2) 0.22752(19) 0.50656(14) 0.0568(5) Uani 1 1 d . . . . .
H11 H 0.331536 0.260381 0.533634 0.068 Uiso 1 1 calc R U . . .
C9 C 0.64960(19) 0.08989(16) 0.52279(12) 0.0461(4) Uani 1 1 d . . . . .
H9 H 0.717662 0.030467 0.560089 0.055 Uiso 1 1 calc R U . . .
C6 C 0.81992(19) 0.54448(16) 0.31647(13) 0.0487(4) Uani 1 1 d . . . . .
H6 H 0.754172 0.492176 0.305330 0.058 Uiso 1 1 calc R U . . .
C14 C 0.57781(19) 0.21986(17) 0.37076(12) 0.0483(4) Uani 1 1 d . . . . .
H14 H 0.598035 0.246898 0.306450 0.058 Uiso 1 1 calc R U . . .
C24 C 0.93871(19) 0.36271(17) 0.89754(13) 0.0491(4) Uani 1 1 d . . . . .
H24 H 0.936548 0.374482 0.833461 0.059 Uiso 1 1 calc R U . . .
C19 C 0.6418(2) -0.09621(18) 0.79226(14) 0.0572(5) Uani 1 1 d . . . . .
H19 H 0.668650 -0.166453 0.771683 0.069 Uiso 1 1 calc R U . . .
C18 C 0.5006(2) -0.08149(16) 0.83648(13) 0.0533(4) Uani 1 1 d . . . . .
H18 H 0.432486 -0.141423 0.845603 0.064 Uiso 1 1 calc R U . . .
C20 C 0.7441(2) -0.00823(18) 0.77807(13) 0.0559(5) Uani 1 1 d . . . . .
H20 H 0.839312 -0.019069 0.748163 0.067 Uiso 1 1 calc R U . . .
C21 C 0.70425(19) 0.09578(17) 0.80848(12) 0.0473(4) Uani 1 1 d . . . . .
H21 H 0.773571 0.154831 0.799198 0.057 Uiso 1 1 calc R U . . .
C5 C 0.7794(2) 0.67135(18) 0.29211(14) 0.0591(5) Uani 1 1 d . . . . .
H5 H 0.686780 0.704177 0.264870 0.071 Uiso 1 1 calc R U . . .
C26 C 1.0570(3) 0.2684(2) 1.04212(18) 0.0716(6) Uani 1 1 d . . . . .
H26 H 1.135374 0.216219 1.075516 0.086 Uiso 1 1 calc R U . . .
C3 C 1.0130(2) 0.70180(16) 0.34973(13) 0.0526(4) Uani 1 1 d . . . . .
H3 H 1.077023 0.755250 0.361053 0.063 Uiso 1 1 calc R U . . .
C34 C 0.2148(2) -0.0421(2) 0.93090(16) 0.0652(5) Uani 1 1 d . . . . .
H34A H 0.124703 -0.013185 0.962142 0.098 Uiso 1 1 calc R U . . .
H34B H 0.188008 -0.053628 0.873220 0.098 Uiso 1 1 calc R U . . .
H34C H 0.258462 -0.119735 0.970186 0.098 Uiso 1 1 calc R U . . .
C4 C 0.8765(2) 0.74843(17) 0.30834(14) 0.0588(5) Uani 1 1 d . . . . .
H4 H 0.849523 0.833807 0.291063 0.071 Uiso 1 1 calc R U . . .
C12 C 0.4479(2) 0.26792(19) 0.41140(14) 0.0575(5) Uani 1 1 d . . . . .
H12 H 0.379820 0.327684 0.374389 0.069 Uiso 1 1 calc R U . . .
C25 C 1.0544(2) 0.2854(2) 0.94830(17) 0.0654(5) Uani 1 1 d . . . . .
H25 H 1.130869 0.244748 0.918198 0.078 Uiso 1 1 calc R U . . .
C10 C 0.5187(2) 0.13881(19) 0.56210(13) 0.0547(4) Uani 1 1 d . . . . .
H10 H 0.497815 0.111721 0.626348 0.066 Uiso 1 1 calc R U . . .
C36 C 0.8275(2) 0.40468(18) 1.03903(12) 0.0548(4) Uani 1 1 d . . . . .
H36 H 0.750319 0.444134 1.069574 0.066 Uiso 1 1 calc R U . . .
C27 C 0.9447(3) 0.3278(2) 1.08823(15) 0.0717(6) Uani 1 1 d . . . . .
H27 H 0.947914 0.316101 1.152244 0.086 Uiso 1 1 calc R U . . .
C15 C 1.3006(3) 0.5951(2) 0.42147(19) 0.0747(6) Uani 1 1 d . . . . .
H15A H 1.387241 0.544051 0.451699 0.112 Uiso 1 1 calc R U . . .
H15B H 1.332054 0.642067 0.359686 0.112 Uiso 1 1 calc R U . . .
H15C H 1.259109 0.650898 0.457023 0.112 Uiso 1 1 calc R U . . .
H1 H 1.012(3) 0.135(2) 0.4404(13) 0.090 Uiso 1 1 d D U . . .
H2 H 0.497(3) 0.402(2) 0.9398(13) 0.090 Uiso 1 1 d 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
S1 O1 1.4378(12) . ?
S1 O2 1.4211(12) . ?
S1 N2 1.6449(14) . ?
S1 C8 1.7576(16) . ?
S2 O4 1.4186(13) . ?
S2 O5 1.4346(12) . ?
S2 N4 1.6495(15) . ?
S2 C23 1.7546(16) . ?
O3 C2 1.358(2) . ?
O3 C15 1.423(2) . ?
O6 C17 1.363(2) . ?
O6 C34 1.427(2) . ?
N1 N2 1.4026(18) . ?
N1 C7 1.267(2) . ?
N2 H1 0.854(16) . ?
N3 N4 1.3974(18) . ?
N3 C22 1.268(2) . ?
N4 H2 0.837(16) . ?
C7 H7 0.9300 . ?
C7 C1 1.463(2) . ?
C16 C17 1.401(2) . ?
C16 C22 1.462(2) . ?
C16 C21 1.389(2) . ?
C17 C18 1.391(2) . ?
C1 C2 1.400(2) . ?
C1 C6 1.391(2) . ?
C23 C24 1.381(2) . ?
C23 C36 1.381(2) . ?
C8 C9 1.381(2) . ?
C8 C14 1.386(2) . ?
C22 H22 0.9300 . ?
C2 C3 1.393(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.375(3) . ?
C11 C10 1.377(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.381(3) . ?
C6 H6 0.9300 . ?
C6 C5 1.383(2) . ?
C14 H14 0.9300 . ?
C14 C12 1.380(2) . ?
C24 H24 0.9300 . ?
C24 C25 1.382(3) . ?
C19 H19 0.9300 . ?
C19 C18 1.376(3) . ?
C19 C20 1.379(3) . ?
C18 H18 0.9300 . ?
C20 H20 0.9300 . ?
C20 C21 1.377(2) . ?
C21 H21 0.9300 . ?
C5 H5 0.9300 . ?
C5 C4 1.370(3) . ?
C26 H26 0.9300 . ?
C26 C25 1.362(3) . ?
C26 C27 1.380(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.376(3) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C4 H4 0.9300 . ?
C12 H12 0.9300 . ?
C25 H25 0.9300 . ?
C10 H10 0.9300 . ?
C36 H36 0.9300 . ?
C36 C27 1.380(3) . ?
C27 H27 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

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
O1 S1 N2 103.83(7) . . ?
O1 S1 C8 110.12(8) . . ?
O2 S1 O1 119.06(8) . . ?
O2 S1 N2 108.16(8) . . ?
O2 S1 C8 108.50(7) . . ?
N2 S1 C8 106.39(7) . . ?
O4 S2 O5 119.31(8) . . ?
O4 S2 N4 108.31(8) . . ?
O4 S2 C23 108.92(8) . . ?
O5 S2 N4 103.59(7) . . ?
O5 S2 C23 109.90(8) . . ?
N4 S2 C23 105.92(7) . . ?
C2 O3 C15 118.08(15) . . ?
C17 O6 C34 118.53(15) . . ?
C7 N1 N2 115.34(13) . . ?
S1 N2 H1 108.4(18) . . ?
N1 N2 S1 112.12(10) . . ?
N1 N2 H1 117.8(17) . . ?
C22 N3 N4 115.83(14) . . ?
S2 N4 H2 111.9(18) . . ?
N3 N4 S2 113.32(10) . . ?
N3 N4 H2 114.2(18) . . ?
N1 C7 H7 119.9 . . ?
N1 C7 C1 120.14(14) . . ?
C1 C7 H7 119.9 . . ?
C17 C16 C22 119.92(14) . . ?
C21 C16 C17 118.73(15) . . ?
C21 C16 C22 121.35(15) . . ?
O6 C17 C16 115.36(14) . . ?
O6 C17 C18 124.65(16) . . ?
C18 C17 C16 119.98(16) . . ?
C2 C1 C7 119.82(14) . . ?
C6 C1 C7 121.25(15) . . ?
C6 C1 C2 118.92(15) . . ?
C24 C23 S2 118.55(12) . . ?
C24 C23 C36 121.27(16) . . ?
C36 C23 S2 120.09(13) . . ?
C9 C8 S1 120.00(12) . . ?
C9 C8 C14 121.18(15) . . ?
C14 C8 S1 118.73(12) . . ?
N3 C22 C16 119.99(15) . . ?
N3 C22 H22 120.0 . . ?
C16 C22 H22 120.0 . . ?
O3 C2 C1 115.55(14) . . ?
O3 C2 C3 124.62(15) . . ?
C3 C2 C1 119.84(16) . . ?
C12 C11 H11 119.7 . . ?
C12 C11 C10 120.54(17) . . ?
C10 C11 H11 119.7 . . ?
C8 C9 H9 120.6 . . ?
C10 C9 C8 118.88(16) . . ?
C10 C9 H9 120.6 . . ?
C1 C6 H6 119.6 . . ?
C5 C6 C1 120.73(17) . . ?
C5 C6 H6 119.6 . . ?
C8 C14 H14 120.5 . . ?
C12 C14 C8 119.08(16) . . ?
C12 C14 H14 120.5 . . ?
C23 C24 H24 120.6 . . ?
C23 C24 C25 118.74(18) . . ?
C25 C24 H24 120.6 . . ?
C18 C19 H19 119.6 . . ?
C18 C19 C20 120.89(17) . . ?
C20 C19 H19 119.6 . . ?
C17 C18 H18 120.1 . . ?
C19 C18 C17 119.75(17) . . ?
C19 C18 H18 120.1 . . ?
C19 C20 H20 120.2 . . ?
C21 C20 C19 119.52(17) . . ?
C21 C20 H20 120.2 . . ?
C16 C21 H21 119.4 . . ?
C20 C21 C16 121.11(17) . . ?
C20 C21 H21 119.4 . . ?
C6 C5 H5 120.2 . . ?
C4 C5 C6 119.62(18) . . ?
C4 C5 H5 120.2 . . ?
C25 C26 H26 119.6 . . ?
C25 C26 C27 120.79(19) . . ?
C27 C26 H26 119.6 . . ?
C2 C3 H3 120.2 . . ?
C4 C3 C2 119.69(17) . . ?
C4 C3 H3 120.2 . . ?
O6 C34 H34A 109.5 . . ?
O6 C34 H34B 109.5 . . ?
O6 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C5 C4 C3 121.19(17) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C11 C12 C14 120.06(16) . . ?
C11 C12 H12 120.0 . . ?
C14 C12 H12 120.0 . . ?
C24 C25 H25 119.8 . . ?
C26 C25 C24 120.4(2) . . ?
C26 C25 H25 119.8 . . ?
C11 C10 C9 120.26(17) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C23 C36 H36 120.5 . . ?
C27 C36 C23 119.01(19) . . ?
C27 C36 H36 120.5 . . ?
C26 C27 C36 119.8(2) . . ?
C26 C27 H27 120.1 . . ?
C36 C27 H27 120.1 . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

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
C34 H34B O2 0.96 2.47 3.419(3) 168.7 2_656
C34 H34B O2 0.96 2.47 3.419(3) 168.7 2_656
N2 H1 O1 0.854(16) 2.059(17) 2.9073(19) 172(2) 2_756
N2 H1 O1 0.854(16) 2.059(17) 2.9073(19) 172(2) 2_756
N4 H2 O5 0.837(16) 2.095(17) 2.915(2) 166(3) 2_667
N4 H2 O5 0.837(16) 2.095(17) 2.915(2) 166(3) 2_667

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
S1 C8 C9 C10 176.92(13) . . . . ?
S1 C8 C14 C12 -176.75(14) . . . . ?
S2 C23 C24 C25 -177.18(14) . . . . ?
S2 C23 C36 C27 177.62(15) . . . . ?
O1 S1 N2 N1 -167.31(11) . . . . ?
O1 S1 C8 C9 28.42(15) . . . . ?
O1 S1 C8 C14 -155.02(13) . . . . ?
O4 S2 N4 N3 58.90(13) . . . . ?
O4 S2 C23 C24 -26.55(16) . . . . ?
O4 S2 C23 C36 156.80(14) . . . . ?
O2 S1 N2 N1 65.30(13) . . . . ?
O2 S1 C8 C9 160.35(13) . . . . ?
O2 S1 C8 C14 -23.10(15) . . . . ?
O3 C2 C3 C4 179.84(16) . . . . ?
O6 C17 C18 C19 179.91(17) . . . . ?
N1 C7 C1 C2 -165.20(15) . . . . ?
N1 C7 C1 C6 15.9(2) . . . . ?
O5 S2 N4 N3 -173.48(12) . . . . ?
O5 S2 C23 C24 -158.95(13) . . . . ?
O5 S2 C23 C36 24.40(16) . . . . ?
N2 S1 C8 C9 -83.49(14) . . . . ?
N2 S1 C8 C14 93.07(14) . . . . ?
N2 N1 C7 C1 -177.67(13) . . . . ?
N4 S2 C23 C24 89.75(14) . . . . ?
N4 S2 C23 C36 -86.90(15) . . . . ?
N4 N3 C22 C16 179.64(13) . . . . ?
C7 N1 N2 S1 157.54(12) . . . . ?
C7 C1 C2 O3 0.5(2) . . . . ?
C7 C1 C2 C3 -179.56(15) . . . . ?
C7 C1 C6 C5 179.52(17) . . . . ?
C16 C17 C18 C19 0.6(3) . . . . ?
C17 C16 C22 N3 -162.91(15) . . . . ?
C17 C16 C21 C20 0.9(2) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
C1 C6 C5 C4 0.1(3) . . . . ?
C23 S2 N4 N3 -57.81(13) . . . . ?
C23 C24 C25 C26 0.0(3) . . . . ?
C23 C36 C27 C26 -1.0(3) . . . . ?
C8 S1 N2 N1 -51.10(13) . . . . ?
C8 C9 C10 C11 -0.5(3) . . . . ?
C8 C14 C12 C11 0.1(3) . . . . ?
C22 N3 N4 S2 155.75(13) . . . . ?
C22 C16 C17 O6 0.0(2) . . . . ?
C22 C16 C17 C18 179.36(15) . . . . ?
C22 C16 C21 C20 -179.48(15) . . . . ?
C2 C1 C6 C5 0.6(3) . . . . ?
C2 C3 C4 C5 0.9(3) . . . . ?
C9 C8 C14 C12 -0.2(3) . . . . ?
C6 C1 C2 O3 179.41(15) . . . . ?
C6 C1 C2 C3 -0.7(2) . . . . ?
C6 C5 C4 C3 -0.9(3) . . . . ?
C14 C8 C9 C10 0.4(3) . . . . ?
C24 C23 C36 C27 1.1(3) . . . . ?
C19 C20 C21 C16 -0.4(3) . . . . ?
C18 C19 C20 C21 -0.1(3) . . . . ?
C20 C19 C18 C17 -0.1(3) . . . . ?
C21 C16 C17 O6 179.61(14) . . . . ?
C21 C16 C17 C18 -1.0(2) . . . . ?
C21 C16 C22 N3 17.5(2) . . . . ?
C34 O6 C17 C16 -178.74(16) . . . . ?
C34 O6 C17 C18 1.9(3) . . . . ?
C12 C11 C10 C9 0.4(3) . . . . ?
C25 C26 C27 C36 0.5(3) . . . . ?
C10 C11 C12 C14 -0.2(3) . . . . ?
C36 C23 C24 C25 -0.6(3) . . . . ?
C27 C26 C25 C24 0.0(3) . . . . ?
C15 O3 C2 C1 170.39(17) . . . . ?
C15 O3 C2 C3 -9.5(3) . . . . ?
_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.
;
####################################################################### 
# 
# 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_nadeem_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1547642'
_audit_update_record             
;
2017-05-03 deposited with the CCDC.
2017-12-06 downloaded from the CCDC.
;
_audit_creation_date             2017-04-30
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            
;
N'-[(E)-(4-methoxyphenyl)methylidene]benzenesulfonohydrazide
;
_chemical_name_systematic        
;
N'-[(E)-(4-methoxyphenyl)methylidene]benzenesulfonohydrazide
;
_chemical_formula_moiety         'C14 H14 N2 O3 S'
_chemical_formula_sum            'C14 H14 N2 O3 S'
_chemical_formula_weight         290.33
_chemical_melting_point          ?
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_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                   12.1076(9)
_cell_length_b                   8.0030(4)
_cell_length_c                   15.9338(13)
_cell_angle_alpha                90
_cell_angle_beta                 110.860(9)
_cell_angle_gamma                90
_cell_volume                     1442.74(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2028
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.9300
_cell_measurement_theta_min      3.3596
_exptl_absorpt_coefficient_mu    0.232
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74393
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.32
_exptl_special_details           ?
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.891
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6926
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.891
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.994
_diffrn_reflns_theta_min         3.602
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.891
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas, CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2378
_reflns_number_total             3416
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2012)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2012)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2012)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.865
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3416
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0538
_refine_ls_restrained_S_all      0.863
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0911P)²+0.8560P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1417
_refine_ls_wR_factor_ref         0.1697
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.1582(2) 0.2073(3) 0.5569(2) 0.0649(7) Uani 1 1 d . . . . .
C2 C 0.1470(3) 0.1322(4) 0.4764(2) 0.0727(8) Uani 1 1 d . . . . .
H2 H 0.211520 0.079021 0.469443 0.087 Uiso 1 1 calc R U . . .
C3 C 0.0391(3) 0.1363(4) 0.4057(3) 0.0939(11) Uani 1 1 d D . . . .
C4A C -0.0453(10) 0.228(3) 0.4262(17) 0.100(3) Uani 0.5 1 d D . P A 1
H4A H -0.115840 0.237533 0.377548 0.120 Uiso 0.5 1 calc R U P A 1
C5A C -0.049(2) 0.309(5) 0.5012(18) 0.112(4) Uani 0.5 1 d D . P A 1
H5A H -0.113315 0.365617 0.507001 0.135 Uiso 0.5 1 calc R U P A 1
C4B C -0.0666(10) 0.202(3) 0.4049(17) 0.100(3) Uani 0.5 1 d D . P A 2
H4B H -0.139486 0.198662 0.358275 0.120 Uiso 0.5 1 calc R U P A 2
C5B C -0.040(2) 0.273(5) 0.4889(17) 0.112(4) Uani 0.5 1 d D . P A 2
H5B H -0.105238 0.324306 0.495635 0.135 Uiso 0.5 1 calc R U P A 2
C6 C 0.0610(3) 0.2869(4) 0.5660(3) 0.0938(11) Uani 1 1 d D . . . .
H6 H 0.071705 0.330522 0.622471 0.113 Uiso 1 1 calc R U . A 1
C7 C 0.2683(2) 0.2059(3) 0.63432(19) 0.0608(6) Uani 1 1 d . . . . .
H7 H 0.269434 0.255233 0.687462 0.073 Uiso 1 1 calc R U . . .
C8 C 0.61900(19) 0.2389(3) 0.63545(15) 0.0493(5) Uani 1 1 d . . . . .
C9 C 0.6590(4) 0.3955(4) 0.6658(3) 0.0880(11) Uani 1 1 d . . . . .
H9 H 0.669711 0.426633 0.724464 0.106 Uiso 1 1 calc R U . . .
C10 C 0.6830(5) 0.5061(4) 0.6086(3) 0.1174(16) Uani 1 1 d . . . . .
H10 H 0.710169 0.612902 0.628549 0.141 Uiso 1 1 calc R U . . .
C11 C 0.6670(3) 0.4597(5) 0.5220(3) 0.0956(11) Uani 1 1 d . . . . .
H11 H 0.681940 0.535674 0.483177 0.115 Uiso 1 1 calc R U . . .
C12 C 0.6300(3) 0.3050(6) 0.4934(2) 0.0941(11) Uani 1 1 d . . . . .
H12 H 0.620873 0.273995 0.435110 0.113 Uiso 1 1 calc R U . . .
C13 C 0.6053(3) 0.1919(4) 0.54889(18) 0.0755(8) Uani 1 1 d . . . . .
H13 H 0.579593 0.084833 0.528488 0.091 Uiso 1 1 calc R U . . .
C14A C 0.0993(6) -0.0212(11) 0.3133(4) 0.122(2) Uani 0.75 1 d . U P B 1
H14A H 0.072230 -0.063434 0.252986 0.183 Uiso 0.75 1 calc R U P B 1
H14B H 0.167968 0.047098 0.323350 0.183 Uiso 0.75 1 calc R U P B 1
H14C H 0.118897 -0.112930 0.354854 0.183 Uiso 0.75 1 calc R U P B 1
N1 N 0.36267(18) 0.1399(3) 0.63209(13) 0.0546(5) Uani 1 1 d . . . . .
N2 N 0.45907(18) 0.1492(3) 0.71303(14) 0.0582(5) Uani 1 1 d . . . . .
H2A H 0.451268 0.179800 0.762362 0.070 Uiso 1 1 calc R U . . .
O1 O 0.57532(17) -0.0653(2) 0.66942(12) 0.0657(5) Uani 1 1 d . . . . .
O2 O 0.66834(17) 0.1239(3) 0.79766(11) 0.0711(5) Uani 1 1 d . . . . .
O3 O 0.0188(4) 0.0651(5) 0.3248(2) 0.1520(15) Uani 1 1 d . . . . .
S1 S 0.58731(5) 0.09845(8) 0.70812(4) 0.0522(2) Uani 1 1 d . . . . .
C14B C -0.0417(15) 0.015(3) 0.2460(10) 0.122(2) Uani 0.25 1 d . . P B 2
H14D H 0.009766 -0.035965 0.219507 0.183 Uiso 0.25 1 calc R U P B 2
H14E H -0.099247 -0.064771 0.248993 0.183 Uiso 0.25 1 calc R U P B 2
H14F H -0.081125 0.108762 0.210107 0.183 Uiso 0.25 1 calc R U P B 2


_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 C2 1.379(4) . ?
C1 C6 1.391(4) . ?
C1 C7 1.458(4) . ?
C2 C3 1.389(4) . ?
C3 C4A 1.389(15) . ?
C3 C4B 1.378(14) . ?
C3 O3 1.350(5) . ?
C4A C5A 1.373(16) . ?
C5A C6 1.379(15) . ?
C4B C5B 1.384(15) . ?
C5B C6 1.394(15) . ?
C7 N1 1.271(3) . ?
C8 C9 1.368(4) . ?
C8 C13 1.381(3) . ?
C8 S1 1.751(2) . ?
C9 C10 1.375(5) . ?
C10 C11 1.375(6) . ?
C11 C12 1.339(6) . ?
C12 C13 1.370(4) . ?
C14A O3 1.260(7) . ?
N1 N2 1.400(3) . ?
N2 S1 1.633(2) . ?
O1 S1 1.4333(19) . ?
O2 S1 1.4293(18) . ?
O3 C14B 1.271(16) . ?

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
C2 C1 C6 119.4(3) . . ?
C2 C1 C7 122.8(3) . . ?
C6 C1 C7 117.9(3) . . ?
C1 C2 C3 119.8(3) . . ?
C2 C3 C4A 112.4(8) . . ?
C4B C3 C2 128.3(9) . . ?
O3 C3 C2 124.3(4) . . ?
O3 C3 C4A 123.3(8) . . ?
O3 C3 C4B 107.3(9) . . ?
C5A C4A C3 135.3(16) . . ?
C4A C5A C6 105.4(16) . . ?
C3 C4B C5B 104.6(15) . . ?
C4B C5B C6 135.6(18) . . ?
C1 C6 C5B 112.4(10) . . ?
C5A C6 C1 127.6(11) . . ?
N1 C7 C1 122.6(3) . . ?
C9 C8 C13 120.3(3) . . ?
C9 C8 S1 119.1(2) . . ?
C13 C8 S1 120.6(2) . . ?
C8 C9 C10 119.1(3) . . ?
C11 C10 C9 120.3(3) . . ?
C12 C11 C10 120.1(3) . . ?
C11 C12 C13 121.0(3) . . ?
C12 C13 C8 119.2(3) . . ?
C7 N1 N2 114.5(2) . . ?
N1 N2 S1 115.95(16) . . ?
C14A O3 C3 118.9(4) . . ?
C14B O3 C3 157.1(10) . . ?
N2 S1 C8 107.93(11) . . ?
O1 S1 C8 108.34(11) . . ?
O1 S1 N2 107.19(12) . . ?
O2 S1 C8 109.52(11) . . ?
O2 S1 N2 104.06(11) . . ?
O2 S1 O1 119.23(12) . . ?

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
C12 H12 O2 0.93 2.59 3.362(4) 141.2 4_565
C13 H13 O1 0.93 3.05 3.534(3) 114.5 3_656
N2 H2A O1 0.86 2.39 3.075(3) 137.4 2_656
_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.
;
