# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_3-3
_database_code_depnum_ccdc_archive 'CCDC 1889448'
loop_
_audit_author_name
_audit_author_address
'Bouguerra Manel and Belhouchet Mohamed'
;Physico Chemistry of Solid State Laboratory, Department of Chemistry, Faculty of Sciences of Sfax
Tunisia
;
#Added by publCIF



_audit_update_record             
;
2021-04-26 deposited with the CCDC.	2021-07-12 downloaded from the CCDC.
;
_audit_creation_date             2021-03-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C12 H14 N2 O2 S), 2(O4 S)'
_chemical_formula_sum            'C24 H28 N4 O12 S4'
_chemical_formula_weight         692.74
_chemical_melting_point          ?
_chemical_oxdiff_formula         ?
_chemical_oxdiff_usercomment     ?
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'

_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.
;
_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'
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                   30.1122(18)
_cell_length_b                   11.7047(5)
_cell_length_c                   8.0292(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.307(5)
_cell_angle_gamma                90
_cell_volume                     2812.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2256
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.7050
_cell_measurement_theta_min      2.9400
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.754
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81237
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.636
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_unetI/netI     0.0629
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10170
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.077
_diffrn_reflns_theta_max         67.077
_diffrn_reflns_theta_min         2.953
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4391
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -8.00  41.00   1.00    1.00    --    0.00 -57.00 -60.00   49
  2  ω     32.00 126.00   1.00    2.50    --   55.02  45.00 -30.00   94
  3  ω    104.00 146.00   1.00    3.00    --  110.04  50.00 -90.00   42
  4  ω    120.00 160.00   1.00    3.00    --  110.04 111.00 -90.00   40
  5  ω     98.00 143.00   1.00    2.50    --   55.02 125.00-180.00   45
  6  ω     83.00 134.00   1.00    3.00    --  110.04 178.00 -90.00   51
  7  ω     64.00 174.00   1.00    3.00    --  110.04  38.00   0.00  110
  8  ω     58.00 115.00   1.00    3.00    --  110.04-111.00 120.00   57
  9  ω     55.00  96.00   1.00    3.00    --  110.04-111.00 -30.00   41
 10  ω     35.00 108.00   1.00    3.00    --  110.04-111.00-120.00   73
 11  ω     19.00  75.00   1.00    3.00    --  110.04 -50.00-150.00   56
 12  ω    -45.00  54.00   1.00    2.50    --   55.02 -77.00-120.00   99
 13  ω     27.00  54.00   1.00    3.00    --  110.04-111.00 120.00   27
 14  ω    -82.00 -30.00   1.00    1.00    --    0.00 -57.00 -60.00   52
 15  ω    -93.00 -39.00   1.00    2.50    --  -55.02 125.00 -60.00   54
 16  ω   -144.00 -93.00   1.00    2.50    --  -55.02 -94.00  30.00   51
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0195412000
_diffrn_orient_matrix_UB_12      -0.0091992000
_diffrn_orient_matrix_UB_13      0.1688875000
_diffrn_orient_matrix_UB_21      -0.0446404000
_diffrn_orient_matrix_UB_22      -0.0422781000
_diffrn_orient_matrix_UB_23      -0.0914369000
_diffrn_orient_matrix_UB_31      0.0166246000
_diffrn_orient_matrix_UB_32      -0.1243186000
_diffrn_orient_matrix_UB_33      0.0187585000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3647
_reflns_number_total             5010
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.536
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.093
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         5010
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0832
_refine_ls_R_factor_gt           0.0573
_refine_ls_restrained_S_all      1.055
_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)+(0.0625P)²+3.4906P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1344
_refine_ls_wR_factor_ref         0.1485
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H,H,H,H,H,H,H,H,H,H) groups
2. Restrained distances
 N16A-H16C
 0.87 with sigma of 0.01
 N16A-H16B
 0.87 with sigma of 0.01
 N16A-H16A
 0.87 with sigma of 0.01
 N17A-H17C
 0.87 with sigma of 0.01
 N17A-H17B
 0.87 with sigma of 0.01
 N17A-H17A
 0.87 with sigma of 0.01
 N17B-H17F
 0.87 with sigma of 0.01
 N17B-H17E
 0.87 with sigma of 0.01
 N17B-H17D
 0.87 with sigma of 0.01
 N16B-H16E
 0.87 with sigma of 0.01
 N16B-H16F
 0.87 with sigma of 0.01
 N16B-H16D
 0.87 with sigma of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C2A(H2A), C2B(H2B), C4A(H4A), C4B(H4B), C5A(H5A), C5B(H5B), C6A(H6A),
 C6B(H6B), C9A(H9A), C9B(H9B), C11A(H11A), C11B(H11B), C12A(H12A), C12B(H12B),
 C13A(H13A), C13B(H13B)
;
_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
C1A C 0.57856(14) 0.4091(3) 0.3918(5) 0.0170(9) Uani 1 1 d . . . . .
C1B C 0.91891(15) 0.4187(4) 0.5915(5) 0.0200(9) Uani 1 1 d . . . . .
C2A C 0.62397(14) 0.3918(3) 0.4189(5) 0.0181(9) Uani 1 1 d . . . . .
H2A H 0.6411 0.3893 0.3295 0.022 Uiso 1 1 calc R . . . .
C2B C 0.87559(14) 0.4198(4) 0.5087(5) 0.0183(9) Uani 1 1 d . . . . .
H2B H 0.8615 0.4884 0.4774 0.022 Uiso 1 1 calc R . . . .
C3A C 0.64378(13) 0.3781(3) 0.5828(5) 0.0166(9) Uani 1 1 d . . . . .
C3B C 0.85405(14) 0.3164(4) 0.4742(5) 0.0205(9) Uani 1 1 d . . . . .
C4A C 0.61797(14) 0.3791(3) 0.7154(5) 0.0177(9) Uani 1 1 d . . . . .
H4A H 0.6314 0.3711 0.8247 0.021 Uiso 1 1 calc R . . . .
C4B C 0.87558(15) 0.2138(4) 0.5166(5) 0.0220(10) Uani 1 1 d . . . . .
H4B H 0.8610 0.1448 0.4916 0.026 Uiso 1 1 calc R . . . .
C5A C 0.57226(14) 0.3918(3) 0.6850(5) 0.0191(9) Uani 1 1 d . . . . .
H5A H 0.5549 0.3892 0.7737 0.023 Uiso 1 1 calc R . . . .
C5B C 0.91919(15) 0.2147(4) 0.5970(6) 0.0259(10) Uani 1 1 d . . . . .
H5B H 0.9338 0.1460 0.6238 0.031 Uiso 1 1 calc R . . . .
H16A H 0.7022(16) 0.433(2) 0.583(6) 0.031 Uiso 1 1 d DR . . . .
H16B H 0.7007(16) 0.358(5) 0.716(2) 0.031 Uiso 1 1 d DR . . . .
H16C H 0.7007(16) 0.308(3) 0.555(5) 0.031 Uiso 1 1 d DR . . . .
H16D H 0.7950(16) 0.253(2) 0.416(6) 0.031 Uiso 1 1 d DR . . . .
H16E H 0.8055(16) 0.344(4) 0.299(3) 0.031 Uiso 1 1 d DR . . . .
H16F H 0.7915(14) 0.368(3) 0.453(6) 0.031 Uiso 1 1 d DR . . . .
H17A H 0.7015(16) 0.759(2) 0.117(6) 0.031 Uiso 1 1 d DR . . . .
H17B H 0.7081(14) 0.682(4) 0.248(3) 0.031 Uiso 1 1 d DR . . . .
H17C H 0.7012(16) 0.637(3) 0.085(5) 0.031 Uiso 1 1 d DR . . . .
H17D H 0.7998(16) 0.561(2) 1.011(6) 0.031 Uiso 1 1 d DR . . . .
H17E H 0.8037(16) 0.685(3) 1.051(5) 0.031 Uiso 1 1 d DR . . . .
H17F H 0.7974(15) 0.647(4) 0.884(3) 0.031 Uiso 1 1 d DR . . . .
C6A C 0.55181(15) 0.4087(4) 0.5215(5) 0.0181(9) Uani 1 1 d . . . . .
H6A H 0.5211 0.4193 0.5006 0.022 Uiso 1 1 calc R . . . .
C6B C 0.94090(15) 0.3175(4) 0.6370(5) 0.0216(9) Uani 1 1 d . . . . .
H6B H 0.9696 0.3183 0.6932 0.026 Uiso 1 1 calc R . . . .
C8A C 0.57862(14) 0.5846(4) 0.1676(5) 0.0177(9) Uani 1 1 d . . . . .
C8B C 0.92068(14) 0.5839(3) 0.8423(5) 0.0153(8) Uani 1 1 d . . . . .
C9A C 0.62364(14) 0.5878(4) 0.1418(5) 0.0179(9) Uani 1 1 d . . . . .
H9A H 0.6386 0.5216 0.1164 0.022 Uiso 1 1 calc R . . . .
C9B C 0.87480(13) 0.5978(3) 0.8379(5) 0.0163(8) Uani 1 1 d . . . . .
H9B H 0.8565 0.5936 0.7370 0.020 Uiso 1 1 calc R . . . .
C10A C 0.64556(14) 0.6915(4) 0.1547(5) 0.0195(9) Uani 1 1 d . . . . .
C10B C 0.85684(14) 0.6180(3) 0.9865(5) 0.0164(8) Uani 1 1 d . . . . .
C11A C 0.62297(15) 0.7915(4) 0.1857(6) 0.0253(10) Uani 1 1 d . . . . .
H11A H 0.6381 0.8609 0.1938 0.030 Uiso 1 1 calc R . . . .
C11B C 0.88422(14) 0.6241(3) 1.1385(5) 0.0182(9) Uani 1 1 d . . . . .
H11B H 0.8718 0.6367 1.2380 0.022 Uiso 1 1 calc R . . . .
C12A C 0.57749(16) 0.7870(4) 0.2044(6) 0.0270(10) Uani 1 1 d . . . . .
H12A H 0.5620 0.8540 0.2218 0.032 Uiso 1 1 calc R . . . .
C12B C 0.92964(14) 0.6113(4) 1.1399(5) 0.0195(9) Uani 1 1 d . . . . .
H12B H 0.9480 0.6168 1.2407 0.023 Uiso 1 1 calc R . . . .
C13A C 0.55516(15) 0.6830(4) 0.1973(5) 0.0238(10) Uani 1 1 d . . . . .
H13A H 0.5250 0.6794 0.2123 0.029 Uiso 1 1 calc R . . . .
C13B C 0.94859(14) 0.5900(4) 0.9921(5) 0.0170(8) Uani 1 1 d . . . . .
H13B H 0.9793 0.5802 0.9936 0.020 Uiso 1 1 calc R . . . .
N16A N 0.69190(13) 0.3669(3) 0.6100(4) 0.0189(8) Uani 1 1 d D . . . .
N16B N 0.80721(13) 0.3192(3) 0.4024(5) 0.0207(8) Uani 1 1 d D . . . .
N17A N 0.69327(13) 0.6919(3) 0.1494(5) 0.0200(8) Uani 1 1 d D . . . .
N17B N 0.80887(12) 0.6287(3) 0.9850(4) 0.0179(7) Uani 1 1 d D . . . .
O14A O 0.57304(10) 0.3716(3) 0.0688(3) 0.0221(7) Uani 1 1 d . . . . .
O14B O 0.92609(10) 0.6350(2) 0.5289(3) 0.0202(6) Uani 1 1 d . . . . .
O15A O 0.50736(10) 0.4567(3) 0.1886(3) 0.0215(7) Uani 1 1 d . . . . .
O15B O 0.99076(10) 0.5387(3) 0.6909(4) 0.0222(7) Uani 1 1 d . . . . .
O19B O 0.77454(10) 0.4793(2) 0.5956(4) 0.0219(7) Uani 1 1 d . . . . .
O20B O 0.71763(10) 0.6104(3) 0.4784(4) 0.0266(7) Uani 1 1 d . . . . .
O21B O 0.78195(10) 0.6813(2) 0.6513(3) 0.0193(6) Uani 1 1 d . . . . .
O22B O 0.79036(11) 0.6090(3) 0.3742(4) 0.0252(7) Uani 1 1 d . . . . .
S7A S 0.55479(3) 0.44664(9) 0.18660(12) 0.0174(2) Uani 1 1 d . . . . .
S7B S 0.94346(3) 0.55276(9) 0.65239(12) 0.0168(2) Uani 1 1 d . . . . .
S18B S 0.76677(3) 0.59424(9) 0.52127(12) 0.0179(2) Uani 1 1 d . . . . .
O19A O 0.72133(10) 0.1891(3) 0.4325(3) 0.0221(7) Uani 1 1 d . . . . .
O20A O 0.71310(10) 0.1055(3) 0.7018(3) 0.0211(6) Uani 1 1 d . . . . .
O21A O 0.71959(10) -0.0158(3) 0.4598(4) 0.0225(7) Uani 1 1 d . . . . .
O22A O 0.78356(10) 0.0922(3) 0.5817(4) 0.0213(7) Uani 1 1 d . . . . .
S18A S 0.73355(3) 0.09125(9) 0.54779(12) 0.0167(2) 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
C1A C2A 1.376(6) . ?
C1A C6A 1.385(6) . ?
C1A S7A 1.777(4) . ?
C1B C2B 1.398(6) . ?
C1B C6B 1.387(6) . ?
C1B S7B 1.780(4) . ?
C2A H2A 0.9300 . ?
C2A C3A 1.393(6) . ?
C2B H2B 0.9300 . ?
C2B C3B 1.387(6) . ?
C3A C4A 1.385(6) . ?
C3A N16A 1.447(5) . ?
C3B C4B 1.389(6) . ?
C3B N16B 1.464(6) . ?
C4A H4A 0.9300 . ?
C4A C5A 1.379(6) . ?
C4B H4B 0.9300 . ?
C4B C5B 1.398(6) . ?
C5A H5A 0.9300 . ?
C5A C6A 1.401(6) . ?
C5B H5B 0.9300 . ?
C5B C6B 1.390(6) . ?
C6A H6A 0.9300 . ?
C6B H6B 0.9300 . ?
C8A C9A 1.394(6) . ?
C8A C13A 1.385(6) . ?
C8A S7A 1.781(4) . ?
C8B C9B 1.388(6) . ?
C8B C13B 1.392(6) . ?
C8B S7B 1.777(4) . ?
C9A H9A 0.9300 . ?
C9A C10A 1.380(6) . ?
C9B H9B 0.9300 . ?
C9B C10B 1.384(5) . ?
C10A C11A 1.389(6) . ?
C10A N17A 1.442(6) . ?
C10B C11B 1.397(6) . ?
C10B N17B 1.449(5) . ?
C11A H11A 0.9300 . ?
C11A C12A 1.395(6) . ?
C11B H11B 0.9300 . ?
C11B C12B 1.375(6) . ?
C12A H12A 0.9300 . ?
C12A C13A 1.389(6) . ?
C12B H12B 0.9300 . ?
C12B C13B 1.394(6) . ?
C13A H13A 0.9300 . ?
C13B H13B 0.9300 . ?
N16A H16A 0.870(10) . ?
N16A H16B 0.872(10) . ?
N16A H16C 0.870(10) . ?
N16B H16D 0.874(10) . ?
N16B H16E 0.874(10) . ?
N16B H16F 0.870(10) . ?
N17A H17A 0.876(10) . ?
N17A H17B 0.872(10) . ?
N17A H17C 0.873(10) . ?
N17B H17D 0.875(10) . ?
N17B H17E 0.871(10) . ?
N17B H17F 0.874(10) . ?
O14A S7A 1.442(3) . ?
O14B S7B 1.438(3) . ?
O15A S7A 1.435(3) . ?
O15B S7B 1.433(3) . ?
O19B S18B 1.480(3) . ?
O20B S18B 1.494(3) . ?
O21B S18B 1.494(3) . ?
O22B S18B 1.454(3) . ?
O19A S18A 1.493(3) . ?
O20A S18A 1.451(3) . ?
O21A S18A 1.477(3) . ?
O22A S18A 1.501(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
C2A C1A C6A 122.0(4) . . ?
C2A C1A S7A 118.4(3) . . ?
C6A C1A S7A 119.3(3) . . ?
C2B C1B S7B 117.4(3) . . ?
C6B C1B C2B 121.8(4) . . ?
C6B C1B S7B 120.6(3) . . ?
C1A C2A H2A 120.6 . . ?
C1A C2A C3A 118.8(4) . . ?
C3A C2A H2A 120.6 . . ?
C1B C2B H2B 120.7 . . ?
C3B C2B C1B 118.6(4) . . ?
C3B C2B H2B 120.7 . . ?
C2A C3A N16A 118.1(4) . . ?
C4A C3A C2A 120.5(4) . . ?
C4A C3A N16A 121.4(4) . . ?
C2B C3B C4B 120.7(4) . . ?
C2B C3B N16B 117.9(4) . . ?
C4B C3B N16B 121.3(4) . . ?
C3A C4A H4A 120.1 . . ?
C5A C4A C3A 119.8(4) . . ?
C5A C4A H4A 120.1 . . ?
C3B C4B H4B 120.1 . . ?
C3B C4B C5B 119.8(4) . . ?
C5B C4B H4B 120.1 . . ?
C4A C5A H5A 119.7 . . ?
C4A C5A C6A 120.6(4) . . ?
C6A C5A H5A 119.7 . . ?
C4B C5B H5B 119.8 . . ?
C6B C5B C4B 120.5(4) . . ?
C6B C5B H5B 119.8 . . ?
C1A C6A C5A 118.2(4) . . ?
C1A C6A H6A 120.9 . . ?
C5A C6A H6A 120.9 . . ?
C1B C6B C5B 118.7(4) . . ?
C1B C6B H6B 120.7 . . ?
C5B C6B H6B 120.7 . . ?
C9A C8A S7A 116.4(3) . . ?
C13A C8A C9A 121.7(4) . . ?
C13A C8A S7A 121.4(3) . . ?
C9B C8B C13B 121.4(4) . . ?
C9B C8B S7B 118.6(3) . . ?
C13B C8B S7B 119.9(3) . . ?
C8A C9A H9A 120.7 . . ?
C10A C9A C8A 118.5(4) . . ?
C10A C9A H9A 120.7 . . ?
C8B C9B H9B 120.6 . . ?
C10B C9B C8B 118.7(4) . . ?
C10B C9B H9B 120.6 . . ?
C9A C10A C11A 120.9(4) . . ?
C9A C10A N17A 118.1(4) . . ?
C11A C10A N17A 120.8(4) . . ?
C9B C10B C11B 120.9(4) . . ?
C9B C10B N17B 119.4(4) . . ?
C11B C10B N17B 119.7(4) . . ?
C10A C11A H11A 120.2 . . ?
C10A C11A C12A 119.6(4) . . ?
C12A C11A H11A 120.2 . . ?
C10B C11B H11B 120.2 . . ?
C12B C11B C10B 119.5(4) . . ?
C12B C11B H11B 120.2 . . ?
C11A C12A H12A 119.8 . . ?
C13A C12A C11A 120.3(4) . . ?
C13A C12A H12A 119.8 . . ?
C11B C12B H12B 119.6 . . ?
C11B C12B C13B 120.8(4) . . ?
C13B C12B H12B 119.6 . . ?
C8A C13A C12A 118.8(4) . . ?
C8A C13A H13A 120.6 . . ?
C12A C13A H13A 120.6 . . ?
C8B C13B C12B 118.7(4) . . ?
C8B C13B H13B 120.7 . . ?
C12B C13B H13B 120.7 . . ?
C3A N16A H16A 105(3) . . ?
C3A N16A H16B 111(3) . . ?
C3A N16A H16C 111(3) . . ?
H16A N16A H16B 106(5) . . ?
H16A N16A H16C 116(5) . . ?
H16B N16A H16C 109(5) . . ?
C3B N16B H16D 109(3) . . ?
C3B N16B H16E 110(3) . . ?
C3B N16B H16F 112(3) . . ?
H16D N16B H16E 115(5) . . ?
H16D N16B H16F 106(5) . . ?
H16E N16B H16F 104(5) . . ?
H17A N17A H17B 105(5) . . ?
H17A N17A H17C 113(5) . . ?
H17B N17A H17C 107(5) . . ?
C10A N17A H17A 109(3) . . ?
C10A N17A H17B 113(3) . . ?
C10A N17A H17C 111(3) . . ?
H17D N17B H17E 118(5) . . ?
H17D N17B H17F 110(5) . . ?
H17E N17B H17F 107(5) . . ?
C10B N17B H17D 105(3) . . ?
C10B N17B H17E 108(3) . . ?
C10B N17B H17F 109(3) . . ?
C1A S7A C8A 100.28(19) . . ?
O14A S7A C1A 108.28(19) . . ?
O14A S7A C8A 108.04(19) . . ?
O15A S7A C1A 108.04(19) . . ?
O15A S7A C8A 109.7(2) . . ?
O15A S7A O14A 120.56(18) . . ?
C8B S7B C1B 103.20(19) . . ?
O14B S7B C1B 106.96(19) . . ?
O14B S7B C8B 108.00(18) . . ?
O15B S7B C1B 109.3(2) . . ?
O15B S7B C8B 107.84(18) . . ?
O15B S7B O14B 120.20(18) . . ?
O19B S18B O20B 108.44(19) . . ?
O19B S18B O21B 108.40(17) . . ?
O20B S18B O21B 107.10(17) . . ?
O22B S18B O19B 111.45(18) . . ?
O22B S18B O20B 110.98(19) . . ?
O22B S18B O21B 110.32(18) . . ?
O19A S18A O22A 106.30(18) . . ?
O20A S18A O19A 110.00(17) . . ?
O20A S18A O21A 112.32(18) . . ?
O20A S18A O22A 110.85(18) . . ?
O21A S18A O19A 108.45(17) . . ?
O21A S18A O22A 108.70(17) . . ?

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
C1A C2A C3A C4A 1.6(6) . . . . ?
C1A C2A C3A N16A -176.3(4) . . . . ?
C1B C2B C3B C4B -1.9(6) . . . . ?
C1B C2B C3B N16B 174.1(3) . . . . ?
C2A C1A C6A C5A 1.1(6) . . . . ?
C2A C1A S7A C8A -66.9(4) . . . . ?
C2A C1A S7A O14A 46.2(4) . . . . ?
C2A C1A S7A O15A 178.3(3) . . . . ?
C2A C3A C4A C5A 1.1(6) . . . . ?
C2B C1B C6B C5B 0.7(6) . . . . ?
C2B C1B S7B C8B 81.5(3) . . . . ?
C2B C1B S7B O14B -32.3(4) . . . . ?
C2B C1B S7B O15B -163.9(3) . . . . ?
C2B C3B C4B C5B 0.9(6) . . . . ?
C3A C4A C5A C6A -2.7(6) . . . . ?
C3B C4B C5B C6B 1.0(7) . . . . ?
C4A C5A C6A C1A 1.7(6) . . . . ?
C4B C5B C6B C1B -1.8(7) . . . . ?
C6A C1A C2A C3A -2.7(6) . . . . ?
C6A C1A S7A C8A 107.2(4) . . . . ?
C6A C1A S7A O14A -139.8(3) . . . . ?
C6A C1A S7A O15A -7.6(4) . . . . ?
C6B C1B C2B C3B 1.1(6) . . . . ?
C6B C1B S7B C8B -93.5(4) . . . . ?
C6B C1B S7B O14B 152.7(3) . . . . ?
C6B C1B S7B O15B 21.1(4) . . . . ?
C8A C9A C10A C11A -2.7(6) . . . . ?
C8A C9A C10A N17A 172.1(4) . . . . ?
C8B C9B C10B C11B -0.2(6) . . . . ?
C8B C9B C10B N17B -177.8(4) . . . . ?
C9A C8A C13A C12A -1.2(6) . . . . ?
C9A C8A S7A C1A 74.6(3) . . . . ?
C9A C8A S7A O14A -38.6(4) . . . . ?
C9A C8A S7A O15A -171.9(3) . . . . ?
C9A C10A C11A C12A 0.2(7) . . . . ?
C9B C8B C13B C12B -0.3(6) . . . . ?
C9B C8B S7B C1B -62.4(4) . . . . ?
C9B C8B S7B O14B 50.6(4) . . . . ?
C9B C8B S7B O15B -178.1(3) . . . . ?
C9B C10B C11B C12B 0.9(6) . . . . ?
C10A C11A C12A C13A 1.9(7) . . . . ?
C10B C11B C12B C13B -1.3(6) . . . . ?
C11A C12A C13A C8A -1.5(7) . . . . ?
C11B C12B C13B C8B 1.0(6) . . . . ?
C13A C8A C9A C10A 3.2(6) . . . . ?
C13A C8A S7A C1A -97.8(4) . . . . ?
C13A C8A S7A O14A 149.0(3) . . . . ?
C13A C8A S7A O15A 15.8(4) . . . . ?
C13B C8B C9B C10B -0.1(6) . . . . ?
C13B C8B S7B C1B 115.4(4) . . . . ?
C13B C8B S7B O14B -131.5(3) . . . . ?
C13B C8B S7B O15B -0.2(4) . . . . ?
N16A C3A C4A C5A 178.9(4) . . . . ?
N16B C3B C4B C5B -175.0(4) . . . . ?
N17A C10A C11A C12A -174.5(4) . . . . ?
N17B C10B C11B C12B 178.5(4) . . . . ?
S7A C1A C2A C3A 171.2(3) . . . . ?
S7A C1A C6A C5A -172.8(3) . . . . ?
S7A C8A C9A C10A -169.1(3) . . . . ?
S7A C8A C13A C12A 170.8(3) . . . . ?
S7B C1B C2B C3B -173.9(3) . . . . ?
S7B C1B C6B C5B 175.5(3) . . . . ?
S7B C8B C9B C10B 177.8(3) . . . . ?
S7B C8B C13B C12B -178.2(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.275
_oxdiff_exptl_absorpt_empirical_full_min 0.761
####################################################################### 
# 
# 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_Manel-4-4
_database_code_depnum_ccdc_archive 'CCDC 1889445'
loop_
_audit_author_name
_audit_author_address
'Bouguerra Manel and Belhouchet Mohamed'
;Physico Chemistry of Solid State Laboratory, Department of Chemistry, Faculty of Sciences of Sfax
Tunisia
;
#Added by publCIF



_audit_update_record             
;
2021-04-26 deposited with the CCDC.	2021-07-12 downloaded from the CCDC.
;
_audit_creation_date             2021-03-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C12 H14 N2 O2 S), 2(O4 S)'
_chemical_formula_sum            'C24 H28 N4 O12 S4'
_chemical_formula_weight         692.74
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         ?
_chemical_oxdiff_usercomment     ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_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                   10.6218(4)
_cell_length_b                   9.6697(4)
_cell_length_c                   14.1442(5)
_cell_angle_alpha                90
_cell_angle_beta                 106.322(4)
_cell_angle_gamma                90
_cell_volume                     1394.20(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4901
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.4460
_cell_measurement_theta_min      3.2530
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.787
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60536
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.650
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10111
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.055
_diffrn_reflns_theta_max         67.055
_diffrn_reflns_theta_min         3.256
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4391
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     32.00 143.00   1.00    1.00    --   55.02  45.00  90.00  111
  2  ω    101.00 177.00   1.00    1.00    --  110.04 111.00   0.00   76
  3  ω    105.00 176.00   1.00    1.00    --  110.04  71.00  94.67   71
  4  ω    103.00 177.00   1.00    1.00    --  110.04  77.00  60.00   74
  5  ω     68.00  95.00   1.00    1.00    --  110.04  50.00  90.00   27
  6  ω     69.00 166.00   1.00    1.00    --  110.04  77.00 120.00   97
  7  ω     69.00  96.00   1.00    1.00    --  110.04  54.00 176.20   27
  8  ω     69.00 174.00   1.00    1.00    --  110.04  77.00 150.00  105
  9  ω     70.00  96.00   1.00    1.00    --  110.04  50.00  60.00   26
 10  ω     66.00  98.00   1.00    1.00    --  110.04  63.00 120.00   32
 11  ω     67.00  93.00   1.00    1.00    --  110.04  77.00  60.00   26
 12  ω     66.00  98.00   1.00    1.00    --  110.04  63.00  60.00   32
 13  ω     67.00  94.00   1.00    1.00    --  110.04  75.00 114.05   27
 14  ω     67.00  93.00   1.00    1.00    --  110.04  63.00  90.00   26
 15  ω     67.00  93.00   1.00    1.00    --  110.04  77.00  90.00   26
 16  ω     69.00  95.00   1.00    1.00    --  110.04  72.00 143.12   26
 17  ω     68.00  95.00   1.00    1.00    --  110.04  63.00 150.00   27
 18  ω     67.00  93.00   1.00    1.00    --  110.04  71.00  94.67   26
 19  ω     61.00 148.00   1.00    1.00    --   55.02  61.00 150.00   87
 20  ω     21.00  49.00   1.00    1.00    --    0.00 -99.00 -60.00   28
 21  ω      1.00  47.00   1.00    1.00    --    0.00 -99.00-150.00   46
 22  ω     66.00 169.00   1.00    1.00    --  110.04  63.00-120.00  103
 23  ω     92.00 178.00   1.00    1.00    --  110.04  77.00-180.00   86
 24  ω     85.00 111.00   1.00    1.00    --   55.02  77.00-180.00   26
 25  ω     75.00 100.00   1.00    1.00    --  110.04  50.00-180.00   25
 26  ω     14.00  40.00   1.00    1.00    --   55.02  77.00-180.00   26
 27  ω      6.00  31.00   1.00    1.00    --    0.00  57.00-180.00   25
 28  ω     44.00  69.00   1.00    1.00    --    0.00  57.00-180.00   25
 29  ω    -38.00  -6.00   1.00    1.00    --    0.00  57.00-180.00   32
 30  ω      3.00 104.00   1.00    1.00    --   55.02 -94.00 -30.00  101
 31  ω     19.00 115.00   1.00    1.00    --  110.04-111.00-180.00   96
 32  ω     12.00  56.00   1.00    1.00    --   55.02  61.00 150.00   44
 33  ω    -91.00 -15.00   1.00    1.00    --  -55.02  30.00 150.00   76
 34  ω   -116.00 -78.00   1.00    1.00    --  -55.02-125.00 120.00   38
 35  ω     59.00 133.00   1.00    1.00    --  110.04 178.00-150.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1128765000
_diffrn_orient_matrix_UB_12      -0.0122688000
_diffrn_orient_matrix_UB_13      0.0481304000
_diffrn_orient_matrix_UB_21      0.0890424000
_diffrn_orient_matrix_UB_22      0.0607281000
_diffrn_orient_matrix_UB_23      0.0963306000
_diffrn_orient_matrix_UB_31      -0.0463328000
_diffrn_orient_matrix_UB_32      0.1468257000
_diffrn_orient_matrix_UB_33      -0.0358461000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.845
_reflns_Friedel_fraction_full    0.961
_reflns_Friedel_fraction_max     0.961
_reflns_number_gt                4521
_reflns_number_total             4882
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.557
_refine_diff_density_rms         0.088
_refine_ls_abs_structure_details 
;
 Flack x determined using 1932 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.011(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         4882
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0329
_refine_ls_restrained_S_all      1.062
_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)+(0.0565P)²+0.1645P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0881
_refine_ls_wR_factor_ref         0.0919
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H,H,H,H,H,H,H,H,H,H) groups
2. Restrained distances
 N17A-H17E
 0.87 with sigma of 0.02
 N16A-H16E
 0.87 with sigma of 0.01
 N16A-H16E
 0.87 with sigma of 0.01
 N16A-H16D
 0.87 with sigma of 0.01
 N16A-H16F
 0.87 with sigma of 0.01
 N16B-H16B
 0.87 with sigma of 0.01
 N16B-H16A
 0.87 with sigma of 0.01
 N16B-H16C
 0.87 with sigma of 0.01
 N17A-H17F
 0.87 with sigma of 0.01
 N17A-H17D
 0.87 with sigma of 0.01
 N17A-H17E
 0.87 with sigma of 0.01
 N17B-H17C
 0.87 with sigma of 0.01
 N17B-H17A
 0.87 with sigma of 0.01
 N17B-H17B
 0.87 with sigma of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C2B(H2B), C3B(H3B), C5B(H5B), C6B(H6B), C9B(H9B), C10B(H10B), C12B(H12B),
 C13B(H13B), C2A(H2A), C3A(H3A), C5A(H5A), C6A(H6A), C9A(H9A), C10A(H10A),
 C12A(H12A), C13A(H13A)
;
_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
C1B C 0.4522(4) 0.3843(4) 0.8923(3) 0.0128(7) Uani 1 1 d . . . . .
C2B C 0.5448(3) 0.3561(4) 0.8418(3) 0.0154(8) Uani 1 1 d . . . . .
H2B H 0.6320 0.3818 0.8684 0.019 Uiso 1 1 calc R . . . .
C3B C 0.5053(4) 0.2896(4) 0.7520(3) 0.0185(8) Uani 1 1 d . . . . .
H3B H 0.5655 0.2713 0.7168 0.022 Uiso 1 1 calc R . . . .
C4B C 0.3754(4) 0.2501(4) 0.7147(2) 0.0151(7) Uani 1 1 d . . . . .
C5B C 0.2842(4) 0.2715(4) 0.7667(3) 0.0177(8) Uani 1 1 d . . . . .
H5B H 0.1983 0.2405 0.7418 0.021 Uiso 1 1 calc R . . . .
C6B C 0.3229(4) 0.3396(4) 0.8566(3) 0.0174(8) Uani 1 1 d . . . . .
H6B H 0.2632 0.3553 0.8925 0.021 Uiso 1 1 calc R . . . .
H16A H 0.364(4) 0.249(4) 0.579(3) 0.021 Uiso 1 1 d DR . . . .
H16B H 0.2484(15) 0.190(5) 0.592(3) 0.021 Uiso 1 1 d DR . . . .
H16C H 0.366(4) 0.110(2) 0.612(3) 0.021 Uiso 1 1 d DR . . . .
H17A H 0.643(4) 0.241(3) 1.423(2) 0.021 Uiso 1 1 d DR . . . .
H17B H 0.705(2) 0.138(4) 1.390(3) 0.021 Uiso 1 1 d DR . . . .
H17C H 0.569(3) 0.125(4) 1.386(3) 0.021 Uiso 1 1 d DR . . . .
H16D H -0.117(4) 0.491(3) 0.590(3) 0.021 Uiso 1 1 d DR . . . .
H16E H -0.2061(17) 0.401(4) 0.613(3) 0.021 Uiso 1 1 d DR . . . .
H16F H -0.077(4) 0.354(3) 0.631(3) 0.021 Uiso 1 1 d DR . . . .
H17D H 0.118(4) 0.476(4) 1.427(3) 0.021 Uiso 1 1 d DR . . . .
H17E H 0.2391(14) 0.434(4) 1.414(3) 0.021 Uiso 1 1 d DR . . . .
H17F H 0.133(4) 0.3427(19) 1.388(3) 0.021 Uiso 1 1 d DR . . . .
C8B C 0.5333(4) 0.3815(4) 1.1027(3) 0.0129(7) Uani 1 1 d . . . . .
C9B C 0.6627(4) 0.3447(4) 1.1460(3) 0.0151(8) Uani 1 1 d . . . . .
H9B H 0.7275 0.3671 1.1160 0.018 Uiso 1 1 calc R . . . .
C10B C 0.6939(3) 0.2740(4) 1.2347(3) 0.0139(7) Uani 1 1 d . . . . .
H10B H 0.7801 0.2484 1.2652 0.017 Uiso 1 1 calc R . . . .
C11B C 0.5953(3) 0.2419(4) 1.2773(2) 0.0130(7) Uani 1 1 d . . . . .
C12B C 0.4645(4) 0.2725(4) 1.2312(3) 0.0148(7) Uani 1 1 d . . . . .
H12B H 0.3992 0.2453 1.2595 0.018 Uiso 1 1 calc R . . . .
C13B C 0.4325(4) 0.3434(4) 1.1432(3) 0.0155(7) Uani 1 1 d . . . . .
H13B H 0.3457 0.3655 1.1114 0.019 Uiso 1 1 calc R . . . .
N16B N 0.3336(3) 0.1917(4) 0.6156(2) 0.0177(7) Uani 1 1 d D . . . .
N17B N 0.6290(3) 0.1802(3) 1.3752(2) 0.0132(6) Uani 1 1 d D . . . .
O14B O 0.6167(2) 0.5608(3) 0.99794(18) 0.0152(5) Uani 1 1 d . . . . .
O15B O 0.3826(3) 0.5706(3) 0.99999(18) 0.0165(5) Uani 1 1 d . . . . .
S7B S 0.49710(10) 0.49088(9) 0.99827(7) 0.0126(2) Uani 1 1 d . . . . .
C1A C -0.0257(4) 0.6340(4) 0.9036(2) 0.0120(7) Uani 1 1 d . . . . .
C2A C 0.0727(4) 0.5993(4) 0.8599(3) 0.0148(7) Uani 1 1 d . . . . .
H2A H 0.1595 0.6235 0.8900 0.018 Uiso 1 1 calc R . . . .
C3A C 0.0394(4) 0.5286(4) 0.7715(3) 0.0153(7) Uani 1 1 d . . . . .
H3A H 0.1034 0.5062 0.7406 0.018 Uiso 1 1 calc R . . . .
C4A C -0.0899(3) 0.4915(4) 0.7293(3) 0.0128(7) Uani 1 1 d . . . . .
C5A C -0.1876(3) 0.5214(4) 0.7740(3) 0.0139(7) Uani 1 1 d . . . . .
H5A H -0.2736 0.4933 0.7453 0.017 Uiso 1 1 calc R . . . .
C6A C -0.1551(3) 0.5939(4) 0.8622(3) 0.0142(7) Uani 1 1 d . . . . .
H6A H -0.2190 0.6153 0.8932 0.017 Uiso 1 1 calc R . . . .
C8A C 0.0549(4) 0.6303(4) 1.1143(2) 0.0128(7) Uani 1 1 d . . . . .
C9A C 0.1867(4) 0.6081(4) 1.1629(3) 0.0167(8) Uani 1 1 d . . . . .
H9A H 0.2519 0.6394 1.1361 0.020 Uiso 1 1 calc R . . . .
C10A C 0.2190(4) 0.5382(4) 1.2524(3) 0.0178(8) Uani 1 1 d . . . . .
H10A H 0.3064 0.5230 1.2867 0.021 Uiso 1 1 calc R . . . .
C11A C 0.1193(4) 0.4916(4) 1.2896(3) 0.0135(7) Uani 1 1 d . . . . .
C12A C -0.0118(3) 0.5066(4) 1.2382(3) 0.0172(8) Uani 1 1 d . . . . .
H12A H -0.0767 0.4694 1.2631 0.021 Uiso 1 1 calc R . . . .
C13A C -0.0455(3) 0.5775(4) 1.1495(3) 0.0156(8) Uani 1 1 d . . . . .
H13A H -0.1330 0.5896 1.1144 0.019 Uiso 1 1 calc R . . . .
N16A N -0.1242(3) 0.4275(3) 0.6320(2) 0.0140(6) Uani 1 1 d D . . . .
N17A N 0.1537(3) 0.4296(4) 1.3875(2) 0.0148(6) Uani 1 1 d D . . . .
O14A O 0.1303(2) 0.8162(3) 1.00938(17) 0.0159(5) Uani 1 1 d . . . . .
O15A O -0.1042(2) 0.8131(3) 1.01006(18) 0.0156(5) Uani 1 1 d . . . . .
S7A S 0.01393(8) 0.73992(9) 1.00919(6) 0.0119(2) Uani 1 1 d . . . . .
O19B O 0.3989(2) 0.4100(3) 0.51606(19) 0.0184(6) Uani 1 1 d . . . . .
O20B O 0.5313(3) 0.4666(3) 0.40896(18) 0.0198(6) Uani 1 1 d . . . . .
O21B O 0.6218(2) 0.3232(3) 0.55147(18) 0.0178(6) Uani 1 1 d . . . . .
O22B O 0.5820(2) 0.5655(3) 0.57332(18) 0.0174(6) Uani 1 1 d . . . . .
S18B S 0.53422(8) 0.44212(9) 0.51274(6) 0.0136(2) Uani 1 1 d . . . . .
O19A O 0.0101(3) 0.2017(3) 0.59299(18) 0.0210(6) Uani 1 1 d . . . . .
O20A O -0.1159(2) 0.0742(3) 0.45043(18) 0.0163(5) Uani 1 1 d . . . . .
O21A O -0.0943(3) 0.3227(3) 0.44058(18) 0.0172(6) Uani 1 1 d . . . . .
O22A O 0.0933(3) 0.1752(3) 0.4529(2) 0.0211(6) Uani 1 1 d . . . . .
S18A S -0.02862(8) 0.19551(9) 0.48405(6) 0.0131(2) 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
C1B C2B 1.394(5) . ?
C1B C6B 1.393(5) . ?
C1B S7B 1.770(4) . ?
C2B H2B 0.9300 . ?
C2B C3B 1.380(5) . ?
C3B H3B 0.9300 . ?
C3B C4B 1.385(5) . ?
C4B C5B 1.387(5) . ?
C4B N16B 1.460(5) . ?
C5B H5B 0.9300 . ?
C5B C6B 1.387(5) . ?
C6B H6B 0.9300 . ?
C8B C9B 1.385(5) . ?
C8B C13B 1.398(5) . ?
C8B S7B 1.769(4) . ?
C9B H9B 0.9300 . ?
C9B C10B 1.385(5) . ?
C10B H10B 0.9300 . ?
C10B C11B 1.382(5) . ?
C11B C12B 1.391(5) . ?
C11B N17B 1.457(4) . ?
C12B H12B 0.9300 . ?
C12B C13B 1.377(5) . ?
C13B H13B 0.9300 . ?
N16B H16A 0.877(14) . ?
N16B H16B 0.873(14) . ?
N16B H16C 0.873(14) . ?
N17B H17A 0.875(14) . ?
N17B H17B 0.875(14) . ?
N17B H17C 0.877(14) . ?
O14B S7B 1.440(3) . ?
O15B S7B 1.446(3) . ?
C1A C2A 1.396(5) . ?
C1A C6A 1.389(5) . ?
C1A S7A 1.762(4) . ?
C2A H2A 0.9300 . ?
C2A C3A 1.382(5) . ?
C3A H3A 0.9300 . ?
C3A C4A 1.382(5) . ?
C4A C5A 1.389(5) . ?
C4A N16A 1.459(5) . ?
C5A H5A 0.9300 . ?
C5A C6A 1.387(5) . ?
C6A H6A 0.9300 . ?
C8A C9A 1.392(5) . ?
C8A C13A 1.395(5) . ?
C8A S7A 1.777(4) . ?
C9A H9A 0.9300 . ?
C9A C10A 1.389(5) . ?
C10A H10A 0.9300 . ?
C10A C11A 1.384(5) . ?
C11A C12A 1.386(5) . ?
C11A N17A 1.459(5) . ?
C12A H12A 0.9300 . ?
C12A C13A 1.385(5) . ?
C13A H13A 0.9300 . ?
N16A H16D 0.868(14) . ?
N16A H16E 0.873(10) . ?
N16A H16F 0.878(14) . ?
N17A H17D 0.880(14) . ?
N17A H17E 0.880(13) . ?
N17A H17F 0.868(14) . ?
O14A S7A 1.439(3) . ?
O15A S7A 1.443(3) . ?
O19B S18B 1.484(3) . ?
O20B S18B 1.479(3) . ?
O21B S18B 1.484(3) . ?
O22B S18B 1.473(3) . ?
O19A S18A 1.480(2) . ?
O20A S18A 1.488(3) . ?
O21A S18A 1.462(3) . ?
O22A S18A 1.493(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
C2B C1B S7B 119.1(3) . . ?
C6B C1B C2B 121.3(3) . . ?
C6B C1B S7B 119.4(3) . . ?
C1B C2B H2B 120.4 . . ?
C3B C2B C1B 119.1(3) . . ?
C3B C2B H2B 120.4 . . ?
C2B C3B H3B 120.3 . . ?
C2B C3B C4B 119.4(3) . . ?
C4B C3B H3B 120.3 . . ?
C3B C4B C5B 121.8(3) . . ?
C3B C4B N16B 118.3(3) . . ?
C5B C4B N16B 119.8(3) . . ?
C4B C5B H5B 120.5 . . ?
C4B C5B C6B 119.0(3) . . ?
C6B C5B H5B 120.5 . . ?
C1B C6B H6B 120.4 . . ?
C5B C6B C1B 119.2(3) . . ?
C5B C6B H6B 120.4 . . ?
C9B C8B C13B 122.1(3) . . ?
C9B C8B S7B 118.5(3) . . ?
C13B C8B S7B 119.2(3) . . ?
C8B C9B H9B 120.6 . . ?
C8B C9B C10B 118.8(3) . . ?
C10B C9B H9B 120.6 . . ?
C9B C10B H10B 120.4 . . ?
C11B C10B C9B 119.2(3) . . ?
C11B C10B H10B 120.4 . . ?
C10B C11B C12B 121.8(3) . . ?
C10B C11B N17B 119.5(3) . . ?
C12B C11B N17B 118.6(3) . . ?
C11B C12B H12B 120.3 . . ?
C13B C12B C11B 119.3(3) . . ?
C13B C12B H12B 120.3 . . ?
C8B C13B H13B 120.7 . . ?
C12B C13B C8B 118.6(3) . . ?
C12B C13B H13B 120.7 . . ?
C4B N16B H16A 105(3) . . ?
C4B N16B H16B 112(3) . . ?
C4B N16B H16C 113(3) . . ?
H16A N16B H16B 107(4) . . ?
H16A N16B H16C 109(4) . . ?
H16B N16B H16C 110(4) . . ?
H17A N17B H17B 101(4) . . ?
H17A N17B H17C 105(4) . . ?
H17B N17B H17C 110(4) . . ?
C11B N17B H17A 113(3) . . ?
C11B N17B H17B 113(3) . . ?
C11B N17B H17C 115(3) . . ?
C8B S7B C1B 107.62(18) . . ?
O14B S7B C1B 107.36(16) . . ?
O14B S7B C8B 107.38(16) . . ?
O14B S7B O15B 119.76(16) . . ?
O15B S7B C1B 107.28(16) . . ?
O15B S7B C8B 106.93(16) . . ?
C2A C1A S7A 119.0(3) . . ?
C6A C1A C2A 121.5(3) . . ?
C6A C1A S7A 119.5(3) . . ?
C1A C2A H2A 120.5 . . ?
C3A C2A C1A 119.1(3) . . ?
C3A C2A H2A 120.5 . . ?
C2A C3A H3A 120.3 . . ?
C2A C3A C4A 119.3(3) . . ?
C4A C3A H3A 120.3 . . ?
C3A C4A C5A 121.9(3) . . ?
C3A C4A N16A 118.1(3) . . ?
C5A C4A N16A 119.8(3) . . ?
C4A C5A H5A 120.5 . . ?
C6A C5A C4A 119.0(3) . . ?
C6A C5A H5A 120.5 . . ?
C1A C6A H6A 120.4 . . ?
C5A C6A C1A 119.1(3) . . ?
C5A C6A H6A 120.4 . . ?
C9A C8A C13A 122.0(3) . . ?
C9A C8A S7A 118.8(3) . . ?
C13A C8A S7A 119.0(3) . . ?
C8A C9A H9A 120.6 . . ?
C10A C9A C8A 118.9(3) . . ?
C10A C9A H9A 120.6 . . ?
C9A C10A H10A 120.5 . . ?
C11A C10A C9A 119.0(3) . . ?
C11A C10A H10A 120.5 . . ?
C10A C11A C12A 122.0(3) . . ?
C10A C11A N17A 118.8(3) . . ?
C12A C11A N17A 119.2(3) . . ?
C11A C12A H12A 120.3 . . ?
C13A C12A C11A 119.5(3) . . ?
C13A C12A H12A 120.3 . . ?
C8A C13A H13A 120.8 . . ?
C12A C13A C8A 118.4(3) . . ?
C12A C13A H13A 120.8 . . ?
H16D N16A H16E 106(4) . . ?
H16D N16A H16F 114(4) . . ?
H16E N16A H16F 107(4) . . ?
C4A N16A H16D 107(3) . . ?
C4A N16A H16E 112(3) . . ?
C4A N16A H16F 112(3) . . ?
H17D N17A H17E 106(4) . . ?
H17D N17A H17F 110(4) . . ?
H17E N17A H17F 106(4) . . ?
C11A N17A H17D 111(3) . . ?
C11A N17A H17E 109(3) . . ?
C11A N17A H17F 114(3) . . ?
C1A S7A C8A 107.84(17) . . ?
O14A S7A C1A 107.47(16) . . ?
O14A S7A C8A 107.21(16) . . ?
O14A S7A O15A 119.78(16) . . ?
O15A S7A C1A 106.92(16) . . ?
O15A S7A C8A 107.13(16) . . ?
O20B S18B O19B 108.35(15) . . ?
O20B S18B O21B 109.07(15) . . ?
O21B S18B O19B 109.77(15) . . ?
O22B S18B O19B 109.23(15) . . ?
O22B S18B O20B 110.81(16) . . ?
O22B S18B O21B 109.58(15) . . ?
O19A S18A O20A 109.29(15) . . ?
O19A S18A O22A 107.60(16) . . ?
O20A S18A O22A 108.46(15) . . ?
O21A S18A O19A 111.34(15) . . ?
O21A S18A O20A 110.35(14) . . ?
O21A S18A O22A 109.72(16) . . ?

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
C1B C2B C3B C4B -1.1(5) . . . . ?
C2B C1B C6B C5B -3.1(6) . . . . ?
C2B C1B S7B C8B -100.0(3) . . . . ?
C2B C1B S7B O14B 15.3(3) . . . . ?
C2B C1B S7B O15B 145.3(3) . . . . ?
C2B C3B C4B C5B -2.2(6) . . . . ?
C2B C3B C4B N16B 174.3(4) . . . . ?
C3B C4B C5B C6B 2.9(6) . . . . ?
C4B C5B C6B C1B -0.2(6) . . . . ?
C6B C1B C2B C3B 3.8(6) . . . . ?
C6B C1B S7B C8B 85.1(3) . . . . ?
C6B C1B S7B O14B -159.6(3) . . . . ?
C6B C1B S7B O15B -29.7(3) . . . . ?
C8B C9B C10B C11B 0.1(5) . . . . ?
C9B C8B C13B C12B 3.0(6) . . . . ?
C9B C8B S7B C1B 95.3(3) . . . . ?
C9B C8B S7B O14B -20.0(3) . . . . ?
C9B C8B S7B O15B -149.7(3) . . . . ?
C9B C10B C11B C12B 3.3(6) . . . . ?
C9B C10B C11B N17B -173.8(3) . . . . ?
C10B C11B C12B C13B -3.6(6) . . . . ?
C11B C12B C13B C8B 0.5(6) . . . . ?
C13B C8B C9B C10B -3.3(6) . . . . ?
C13B C8B S7B C1B -89.4(3) . . . . ?
C13B C8B S7B O14B 155.3(3) . . . . ?
C13B C8B S7B O15B 25.6(3) . . . . ?
N16B C4B C5B C6B -173.6(4) . . . . ?
N17B C11B C12B C13B 173.5(3) . . . . ?
S7B C1B C2B C3B -171.1(3) . . . . ?
S7B C1B C6B C5B 171.7(3) . . . . ?
S7B C8B C9B C10B 171.9(3) . . . . ?
S7B C8B C13B C12B -172.2(3) . . . . ?
C1A C2A C3A C4A -1.3(5) . . . . ?
C2A C1A C6A C5A -2.0(5) . . . . ?
C2A C1A S7A C8A -92.8(3) . . . . ?
C2A C1A S7A O14A 22.5(3) . . . . ?
C2A C1A S7A O15A 152.3(3) . . . . ?
C2A C3A C4A C5A -0.9(6) . . . . ?
C2A C3A C4A N16A 174.8(3) . . . . ?
C3A C4A C5A C6A 1.7(6) . . . . ?
C4A C5A C6A C1A -0.3(5) . . . . ?
C6A C1A C2A C3A 2.8(5) . . . . ?
C6A C1A S7A C8A 91.1(3) . . . . ?
C6A C1A S7A O14A -153.6(3) . . . . ?
C6A C1A S7A O15A -23.8(3) . . . . ?
C8A C9A C10A C11A 0.8(6) . . . . ?
C9A C8A C13A C12A 3.2(6) . . . . ?
C9A C8A S7A C1A 100.3(3) . . . . ?
C9A C8A S7A O14A -15.1(3) . . . . ?
C9A C8A S7A O15A -144.9(3) . . . . ?
C9A C10A C11A C12A 3.1(6) . . . . ?
C9A C10A C11A N17A -174.5(4) . . . . ?
C10A C11A C12A C13A -3.9(6) . . . . ?
C11A C12A C13A C8A 0.7(5) . . . . ?
C13A C8A C9A C10A -3.9(6) . . . . ?
C13A C8A S7A C1A -84.3(3) . . . . ?
C13A C8A S7A O14A 160.3(3) . . . . ?
C13A C8A S7A O15A 30.5(3) . . . . ?
N16A C4A C5A C6A -174.0(3) . . . . ?
N17A C11A C12A C13A 173.7(3) . . . . ?
S7A C1A C2A C3A -173.3(3) . . . . ?
S7A C1A C6A C5A 174.0(3) . . . . ?
S7A C8A C9A C10A 171.3(3) . . . . ?
S7A C8A C13A C12A -172.1(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.706
_oxdiff_exptl_absorpt_empirical_full_min 0.598
