# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_17075
_database_code_depnum_ccdc_archive 'CCDC 1589736'
loop_
_audit_author_name
_audit_author_address
'Muhammad Nadeem Arshad' 'King Abdulaziz University'
_audit_update_record             
;
2017-12-07 deposited with the CCDC.	2019-12-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
; 
N'-[(Z)-1,3-benzodioxol-5-ylmethylidene]benzenesulfonohydrazide
;
_chemical_name_common            
;
N'-[(Z)-1,3-benzodioxol-5-ylmethylidene]benzenesulfonohydrazide
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H12 N2 O4 S'
_chemical_formula_sum            'C14 H12 N2 O4 S'
_chemical_formula_weight         304.32

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 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.3559(8)
_cell_length_b                   12.2616(9)
_cell_length_c                   10.7523(8)
_cell_angle_alpha                90
_cell_angle_beta                 91.528(7)
_cell_angle_gamma                90
_cell_volume                     1364.84(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2220
_cell_measurement_theta_min      3.2221
_cell_measurement_theta_max      29.0862

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_absorpt_coefficient_mu    0.255
_exptl_absorpt_correction_T_min  0.45518
_exptl_absorpt_correction_T_max  1.00000
_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_special_details           ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas, CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6171
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.229
_diffrn_reflns_theta_max         29.150
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.878
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.878
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.878
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3236
_reflns_number_gt                2524
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_computing_data_collection       'CrysAlis PRO (Agilent, 2012)'
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2012)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2012)'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0468P)²+0.3462P] 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         3236
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.1100
_refine_ls_wR_factor_gt          0.0983
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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 0.48690(16) 0.42235(14) 0.23346(15) 0.0325(4) Uani 1 1 d . . . . .
C2 C 0.48119(18) 0.35614(15) 0.12949(17) 0.0394(4) Uani 1 1 d . . . . .
H2 H 0.533183 0.294495 0.124956 0.047 Uiso 1 1 calc R U . . .
C3 C 0.39708(19) 0.38290(16) 0.03237(17) 0.0456(5) Uani 1 1 d . . . . .
H3 H 0.391864 0.338651 -0.037838 0.055 Uiso 1 1 calc R U . . .
C4 C 0.32120(19) 0.47432(17) 0.03882(18) 0.0473(5) Uani 1 1 d . . . . .
H4 H 0.265844 0.492360 -0.027544 0.057 Uiso 1 1 calc R U . . .
C5 C 0.3266(2) 0.53962(16) 0.14330(19) 0.0470(5) Uani 1 1 d . . . . .
H5 H 0.274467 0.601198 0.147312 0.056 Uiso 1 1 calc R U . . .
C6 C 0.40891(19) 0.51402(15) 0.24165(17) 0.0409(4) Uani 1 1 d . . . . .
H6 H 0.412214 0.557494 0.312541 0.049 Uiso 1 1 calc R U . . .
C7 C 0.77792(17) 0.63976(16) 0.30520(17) 0.0394(4) Uani 1 1 d . . . . .
H7 H 0.742816 0.680489 0.368957 0.047 Uiso 1 1 calc R U . . .
C8 C 0.85930(16) 0.69417(15) 0.21542(17) 0.0370(4) Uani 1 1 d . . . . .
C9 C 0.93706(16) 0.63477(15) 0.13431(17) 0.0377(4) Uani 1 1 d . . . . .
H9 H 0.941496 0.559062 0.137341 0.045 Uiso 1 1 calc R U . . .
C10 C 1.00558(16) 0.69344(16) 0.05107(16) 0.0373(4) Uani 1 1 d . . . . .
C11 C 1.00070(18) 0.80643(16) 0.04510(17) 0.0402(4) Uani 1 1 d . . . . .
C12 C 0.9271(2) 0.86594(17) 0.1234(2) 0.0523(5) Uani 1 1 d . . . . .
H12 H 0.924285 0.941683 0.119733 0.063 Uiso 1 1 calc R U . . .
C13 C 0.8562(2) 0.80712(16) 0.20944(19) 0.0476(5) Uani 1 1 d . . . . .
H13 H 0.805126 0.845038 0.264630 0.057 Uiso 1 1 calc R U . . .
C14 C 1.1393(2) 0.74863(19) -0.0956(2) 0.0527(5) Uani 1 1 d . . . . .
H14A H 1.125729 0.744730 -0.185127 0.063 Uiso 1 1 calc R U . . .
H14B H 1.231549 0.752272 -0.077747 0.063 Uiso 1 1 calc R U . . .
N1 N 0.67686(14) 0.49725(13) 0.39434(14) 0.0389(4) Uani 1 1 d . . . . .
N2 N 0.75362(14) 0.53793(13) 0.29864(13) 0.0388(4) Uani 1 1 d . . . . .
O1 O 0.51710(13) 0.37092(10) 0.46788(11) 0.0440(3) Uani 1 1 d . . . . .
O2 O 0.67728(14) 0.30528(11) 0.31967(13) 0.0498(4) Uani 1 1 d . . . . .
O3 O 1.08616(14) 0.65498(12) -0.03838(13) 0.0535(4) Uani 1 1 d . . . . .
O4 O 1.07732(14) 0.84286(12) -0.04792(14) 0.0556(4) Uani 1 1 d . . . . .
S1 S 0.59233(4) 0.38875(3) 0.35914(4) 0.03518(14) Uani 1 1 d . . . . .
H1N H 0.6336(19) 0.5377(16) 0.4348(18) 0.042 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 C2 1.382(2) . ?
C1 C6 1.388(2) . ?
C1 S1 1.7633(17) . ?
C2 C3 1.381(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.372(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.379(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.377(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N2 1.275(2) . ?
C7 C8 1.460(3) . ?
C7 H7 0.9300 . ?
C8 C13 1.387(3) . ?
C8 C9 1.406(2) . ?
C9 C10 1.362(3) . ?
C9 H9 0.9300 . ?
C10 O3 1.373(2) . ?
C10 C11 1.388(3) . ?
C11 C12 1.362(3) . ?
C11 O4 1.368(2) . ?
C12 C13 1.397(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 O3 1.421(3) . ?
C14 O4 1.424(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
N1 N2 1.408(2) . ?
N1 S1 1.6316(16) . ?
N1 H1N 0.80(2) . ?
O1 S1 1.4389(13) . ?
O2 S1 1.4217(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
C2 C1 C6 120.98(16) . . ?
C2 C1 S1 119.67(14) . . ?
C6 C1 S1 119.34(13) . . ?
C3 C2 C1 118.98(18) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C4 C3 C2 120.42(18) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 120.30(18) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 120.28(19) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 119.03(17) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N2 C7 C8 121.84(17) . . ?
N2 C7 H7 119.1 . . ?
C8 C7 H7 119.1 . . ?
C13 C8 C9 120.10(18) . . ?
C13 C8 C7 118.30(17) . . ?
C9 C8 C7 121.58(17) . . ?
C10 C9 C8 116.80(17) . . ?
C10 C9 H9 121.6 . . ?
C8 C9 H9 121.6 . . ?
C9 C10 O3 127.99(18) . . ?
C9 C10 C11 122.58(17) . . ?
O3 C10 C11 109.42(17) . . ?
C12 C11 O4 128.44(19) . . ?
C12 C11 C10 121.77(18) . . ?
O4 C11 C10 109.79(17) . . ?
C11 C12 C13 116.44(19) . . ?
C11 C12 H12 121.8 . . ?
C13 C12 H12 121.8 . . ?
C8 C13 C12 122.30(19) . . ?
C8 C13 H13 118.9 . . ?
C12 C13 H13 118.9 . . ?
O3 C14 O4 108.41(16) . . ?
O3 C14 H14A 110.0 . . ?
O4 C14 H14A 110.0 . . ?
O3 C14 H14B 110.0 . . ?
O4 C14 H14B 110.0 . . ?
H14A C14 H14B 108.4 . . ?
N2 N1 S1 115.41(12) . . ?
N2 N1 H1N 120.7(15) . . ?
S1 N1 H1N 109.0(15) . . ?
C7 N2 N1 114.88(16) . . ?
C10 O3 C14 106.00(16) . . ?
C11 O4 C14 105.93(16) . . ?
O2 S1 O1 119.07(8) . . ?
O2 S1 N1 108.90(9) . . ?
O1 S1 N1 103.54(8) . . ?
O2 S1 C1 108.35(8) . . ?
O1 S1 C1 108.70(8) . . ?
N1 S1 C1 107.74(8) . . ?

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 0.6(3) . . . . ?
S1 C1 C2 C3 179.30(14) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C2 C3 C4 C5 -1.0(3) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C4 C5 C6 C1 0.6(3) . . . . ?
C2 C1 C6 C5 -1.1(3) . . . . ?
S1 C1 C6 C5 -179.85(15) . . . . ?
N2 C7 C8 C13 164.51(18) . . . . ?
N2 C7 C8 C9 -14.0(3) . . . . ?
C13 C8 C9 C10 -0.8(2) . . . . ?
C7 C8 C9 C10 177.63(15) . . . . ?
C8 C9 C10 O3 -178.93(16) . . . . ?
C8 C9 C10 C11 0.2(3) . . . . ?
C9 C10 C11 C12 0.5(3) . . . . ?
O3 C10 C11 C12 179.71(17) . . . . ?
C9 C10 C11 O4 -179.11(15) . . . . ?
O3 C10 C11 O4 0.1(2) . . . . ?
O4 C11 C12 C13 179.07(18) . . . . ?
C10 C11 C12 C13 -0.4(3) . . . . ?
C9 C8 C13 C12 0.9(3) . . . . ?
C7 C8 C13 C12 -177.61(18) . . . . ?
C11 C12 C13 C8 -0.3(3) . . . . ?
C8 C7 N2 N1 178.14(14) . . . . ?
S1 N1 N2 C7 153.69(14) . . . . ?
C9 C10 O3 C14 -176.82(18) . . . . ?
C11 C10 O3 C14 4.0(2) . . . . ?
O4 C14 O3 C10 -6.6(2) . . . . ?
C12 C11 O4 C14 176.3(2) . . . . ?
C10 C11 O4 C14 -4.2(2) . . . . ?
O3 C14 O4 C11 6.6(2) . . . . ?
N2 N1 S1 O2 56.80(14) . . . . ?
N2 N1 S1 O1 -175.56(12) . . . . ?
N2 N1 S1 C1 -60.52(14) . . . . ?
C2 C1 S1 O2 11.90(17) . . . . ?
C6 C1 S1 O2 -169.35(14) . . . . ?
C2 C1 S1 O1 -118.85(15) . . . . ?
C6 C1 S1 O1 59.90(16) . . . . ?
C2 C1 S1 N1 129.57(15) . . . . ?
C6 C1 S1 N1 -51.68(16) . . . . ?

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
C5 H5 O2 0.93 2.57 3.282(2) 133.2 2_655
N1 H1N O1 0.80(2) 2.21(2) 3.000(2) 168.8(19) 3_666

_refine_diff_density_max         0.279
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_17073
_database_code_depnum_ccdc_archive 'CCDC 1589737'
loop_
_audit_author_name
_audit_author_address
'Muhammad Nadeem Arshad' 'King Abdulaziz University'
_audit_update_record             
;
2017-12-07 deposited with the CCDC.	2019-12-27 downloaded from the CCDC.
;
_audit_creation_date             2017-12-06
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            
;
N'-[(Z)-1,3-benzodioxol-5-ylmethylidene]-4-methyl
benzenesulfonohydrazide
;
_chemical_name_systematic        
;
N'-[(Z)-1,3-benzodioxol-5-ylmethylidene]-4-methyl
benzenesulfonohydrazide
;
_chemical_formula_moiety         'C15 H14 N2 O4 S'
_chemical_formula_sum            'C15 H14 N2 O4 S'
_chemical_formula_weight         318.34
_chemical_absolute_configuration ?
_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'
Br Br -0.2901 2.4595 '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      hexagonal
_space_group_IT_number           170
_space_group_name_H-M_alt        'P 65'
_space_group_name_Hall           'P 65'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x-y, x, z+5/6'
'-y, x-y, z+2/3'
'-x, -y, z+1/2'
'-x+y, -x, z+1/3'
'y, -x+y, z+1/6'

_cell_length_a                   11.4162(4)
_cell_length_b                   11.4162(4)
_cell_length_c                   20.9435(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     2363.87(18)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    7449
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.1205
_cell_measurement_theta_min      2.8277
_exptl_absorpt_coefficient_mu    0.224
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73260
_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    1.342
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             996
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.24
_exptl_special_details           ?
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0971
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.860
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5104
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.860
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.071
_diffrn_reflns_theta_min         3.178
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.860
_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                1843
_reflns_number_total             3354
_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-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.07(12)
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3955
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0851
_refine_ls_R_factor_gt           0.0458
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_wR_factor_gt          0.1219
_refine_ls_wR_factor_ref         0.1426
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 -0.0989(4) 0.3209(4) 0.62694(19) 0.0664(9) Uani 1 1 d . . . . .
C2 C 0.0398(4) 0.3766(5) 0.6237(2) 0.0822(12) Uani 1 1 d . . . . .
H2 H 0.086595 0.364105 0.656904 0.099 Uiso 1 1 calc R U . . .
C3 C 0.1076(5) 0.4507(6) 0.5708(3) 0.0950(14) Uani 1 1 d . . . . .
H3 H 0.200870 0.487814 0.568324 0.114 Uiso 1 1 calc R U . . .
C4 C 0.0402(5) 0.4712(5) 0.5212(3) 0.0927(13) Uani 1 1 d . . . . .
C5 C -0.0983(5) 0.4126(5) 0.5252(2) 0.0901(13) Uani 1 1 d . . . . .
H5 H -0.145346 0.424837 0.492018 0.108 Uiso 1 1 calc R U . . .
C6 C -0.1680(5) 0.3367(5) 0.5769(2) 0.0794(12) Uani 1 1 d . . . . .
H6 H -0.261735 0.295914 0.578332 0.095 Uiso 1 1 calc R U . . .
C7 C -0.1140(4) -0.0523(4) 0.66694(19) 0.0689(9) Uani 1 1 d . . . . .
H7 H -0.202673 -0.122347 0.662334 0.083 Uiso 1 1 calc R U . . .
C8 C -0.0058(5) -0.0817(4) 0.65853(19) 0.0730(10) Uani 1 1 d . . . . .
C9 C 0.1273(5) 0.0197(5) 0.6618(2) 0.0863(13) Uani 1 1 d . . . . .
H9 H 0.151543 0.108362 0.671709 0.104 Uiso 1 1 calc R U . . .
C10 C 0.2226(5) -0.0180(7) 0.6495(3) 0.1058(17) Uani 1 1 d . . . . .
C11 C 0.1857(7) -0.1499(7) 0.6366(3) 0.1057(18) Uani 1 1 d . . . . .
C12 C 0.0599(7) -0.2486(7) 0.6336(3) 0.1075(18) Uani 1 1 d . . . . .
H12 H 0.037760 -0.336848 0.623961 0.129 Uiso 1 1 calc R U . . .
C13 C -0.0382(6) -0.2139(5) 0.6457(2) 0.0888(12) Uani 1 1 d . . . . .
H13 H -0.128719 -0.281314 0.645185 0.107 Uiso 1 1 calc R U . . .
C14 C 0.4083(8) -0.0244(10) 0.6246(5) 0.149(3) Uani 1 1 d . . . . .
H14A H 0.444742 0.001381 0.581830 0.179 Uiso 1 1 calc R U . . .
H14B H 0.480150 -0.015374 0.652551 0.179 Uiso 1 1 calc R U . . .
C15 C 0.1178(8) 0.5551(8) 0.4643(3) 0.139(3) Uani 1 1 d . . . . .
H15A H 0.170297 0.518766 0.446211 0.209 Uiso 1 1 calc R U . . .
H15B H 0.177049 0.646706 0.477554 0.209 Uiso 1 1 calc R U . . .
H15C H 0.055627 0.553068 0.432886 0.209 Uiso 1 1 calc R U . . .
N1 N -0.2116(3) 0.0736(3) 0.68594(17) 0.0707(8) Uani 1 1 d . . . . .
H1N H -0.291202 0.003416 0.685026 0.085 Uiso 1 1 calc R U . . .
N2 N -0.0933(3) 0.0656(3) 0.68041(15) 0.0675(8) Uani 1 1 d . . . . .
O1 O -0.3183(3) 0.2102(3) 0.69477(15) 0.0876(8) Uani 1 1 d . . . . .
O2 O -0.1003(4) 0.2843(3) 0.74842(14) 0.0847(9) Uani 1 1 d . . . . .
O3 O 0.3581(4) 0.0643(6) 0.6467(3) 0.155(2) Uani 1 1 d . . . . .
O4 O 0.3049(6) -0.1550(7) 0.6247(3) 0.154(2) Uani 1 1 d . . . . .
S1 S -0.18638(10) 0.22619(10) 0.69421(4) 0.0694(3) Uani 1 1 d . . . . .


_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 1.382(6) . ?
C1 C6 1.376(6) . ?
C1 S1 1.753(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.374(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.380(7) . ?
C4 C5 1.377(7) . ?
C4 C15 1.508(8) . ?
C5 H5 0.9300 . ?
C5 C6 1.367(7) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.443(6) . ?
C7 N2 1.276(5) . ?
C8 C9 1.376(7) . ?
C8 C13 1.389(6) . ?
C9 H9 0.9300 . ?
C9 C10 1.379(7) . ?
C10 C11 1.372(8) . ?
C10 O3 1.351(7) . ?
C11 C12 1.311(8) . ?
C11 O4 1.414(7) . ?
C12 H12 0.9300 . ?
C12 C13 1.385(7) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 O3 1.466(8) . ?
C14 O4 1.363(10) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
N1 H1N 0.8600 . ?
N1 N2 1.404(4) . ?
N1 S1 1.626(3) . ?
O1 S1 1.424(3) . ?
O2 S1 1.430(3) . ?

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 S1 119.4(3) . . ?
C6 C1 C2 120.2(4) . . ?
C6 C1 S1 120.4(3) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 C1 119.0(4) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 119.3 . . ?
C2 C3 C4 121.4(5) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 C15 120.1(5) . . ?
C5 C4 C3 118.3(5) . . ?
C5 C4 C15 121.6(5) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 C4 121.2(4) . . ?
C6 C5 H5 119.4 . . ?
C1 C6 H6 120.1 . . ?
C5 C6 C1 119.8(5) . . ?
C5 C6 H6 120.1 . . ?
C8 C7 H7 118.5 . . ?
N2 C7 H7 118.5 . . ?
N2 C7 C8 122.9(4) . . ?
C9 C8 C7 120.8(4) . . ?
C9 C8 C13 120.4(4) . . ?
C13 C8 C7 118.9(4) . . ?
C8 C9 H9 122.0 . . ?
C8 C9 C10 116.1(5) . . ?
C10 C9 H9 122.0 . . ?
C11 C10 C9 121.4(5) . . ?
O3 C10 C9 126.8(6) . . ?
O3 C10 C11 111.8(5) . . ?
C10 C11 O4 107.8(6) . . ?
C12 C11 C10 123.8(5) . . ?
C12 C11 O4 128.3(5) . . ?
C11 C12 H12 121.9 . . ?
C11 C12 C13 116.1(5) . . ?
C13 C12 H12 121.9 . . ?
C8 C13 H13 118.9 . . ?
C12 C13 C8 122.1(6) . . ?
C12 C13 H13 118.9 . . ?
H14A C14 H14B 108.3 . . ?
O3 C14 H14A 109.8 . . ?
O3 C14 H14B 109.8 . . ?
O4 C14 H14A 109.8 . . ?
O4 C14 H14B 109.8 . . ?
O4 C14 O3 109.4(6) . . ?
C4 C15 H15A 109.5 . . ?
C4 C15 H15B 109.5 . . ?
C4 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 N1 H1N 122.7 . . ?
N2 N1 S1 114.7(3) . . ?
S1 N1 H1N 122.7 . . ?
C7 N2 N1 114.2(3) . . ?
C10 O3 C14 103.9(6) . . ?
C14 O4 C11 106.3(5) . . ?
N1 S1 C1 108.47(18) . . ?
O1 S1 C1 109.00(18) . . ?
O1 S1 N1 104.69(18) . . ?
O1 S1 O2 119.41(19) . . ?
O2 S1 C1 107.7(2) . . ?
O2 S1 N1 107.11(18) . . ?

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
C14 H14B O1 0.97 2.60 3.273(9) 126.3 1_655

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
C1 C2 C3 C4 0.4(7) . . . . ?
C2 C1 C6 C5 -2.8(6) . . . . ?
C2 C1 S1 N1 -81.7(4) . . . . ?
C2 C1 S1 O1 164.9(3) . . . . ?
C2 C1 S1 O2 33.9(4) . . . . ?
C2 C3 C4 C5 -1.5(8) . . . . ?
C2 C3 C4 C15 178.9(6) . . . . ?
C3 C4 C5 C6 0.5(8) . . . . ?
C4 C5 C6 C1 1.7(7) . . . . ?
C6 C1 C2 C3 1.8(7) . . . . ?
C6 C1 S1 N1 96.5(3) . . . . ?
C6 C1 S1 O1 -16.9(4) . . . . ?
C6 C1 S1 O2 -147.9(3) . . . . ?
C7 C8 C9 C10 -176.4(4) . . . . ?
C7 C8 C13 C12 176.4(4) . . . . ?
C8 C7 N2 N1 179.3(3) . . . . ?
C8 C9 C10 C11 -1.8(8) . . . . ?
C8 C9 C10 O3 176.4(6) . . . . ?
C9 C8 C13 C12 -2.2(7) . . . . ?
C9 C10 C11 C12 1.4(10) . . . . ?
C9 C10 C11 O4 178.7(6) . . . . ?
C9 C10 O3 C14 -173.3(7) . . . . ?
C10 C11 C12 C13 -1.3(10) . . . . ?
C10 C11 O4 C14 -5.9(8) . . . . ?
C11 C10 O3 C14 5.1(8) . . . . ?
C11 C12 C13 C8 1.7(8) . . . . ?
C12 C11 O4 C14 171.2(7) . . . . ?
C13 C8 C9 C10 2.2(7) . . . . ?
C15 C4 C5 C6 -180.0(6) . . . . ?
N2 C7 C8 C9 -3.2(6) . . . . ?
N2 C7 C8 C13 178.2(4) . . . . ?
N2 N1 S1 C1 60.2(3) . . . . ?
N2 N1 S1 O1 176.5(3) . . . . ?
N2 N1 S1 O2 -55.8(3) . . . . ?
O3 C10 C11 C12 -177.1(7) . . . . ?
O3 C10 C11 O4 0.2(8) . . . . ?
O3 C14 O4 C11 9.1(9) . . . . ?
O4 C11 C12 C13 -178.0(6) . . . . ?
O4 C14 O3 C10 -8.9(9) . . . . ?
S1 C1 C2 C3 180.0(4) . . . . ?
S1 C1 C6 C5 179.0(4) . . . . ?
S1 N1 N2 C7 -172.7(3) . . . . ?
_shelx_SHELXL_version_number     2016/6
_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.
;
