# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_1a
_database_code_depnum_ccdc_archive 'CCDC 2337437'
loop_
_audit_author_name
_audit_author_address
'Rajesh Gonnade'
;CSIR NATIONAL CHEMICAL LABORATORY PUNE INDIA
India
;
_audit_update_record             
;
2024-03-02 deposited with the CCDC.	2024-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H13 F3 O3 S'
_chemical_formula_sum            'C15 H13 F3 O3 S'
_chemical_formula_weight         330.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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                   16.719(6)
_cell_length_b                   7.935(3)
_cell_length_c                   11.680(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.248(6)
_cell_angle_gamma                90
_cell_volume                     1519.8(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3960
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      25.73

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.254
_shelx_estimated_absorpt_T_min   0.951
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.6072
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   SADABS,(BRUKER,2006)
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_source_type              'Incoatech I\mS HB'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            9953
_diffrn_reflns_av_unetI/netI     0.0746
_diffrn_reflns_av_R_equivalents  0.0872
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.242
_diffrn_reflns_theta_max         25.987
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2991
_reflns_number_gt                2356
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL, Mercury 2020.20'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0823P)²+1.8313P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'direct method'
_atom_sites_solution_secondary   'difference Fourier'
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2991
_refine_ls_number_parameters     208
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1001
_refine_ls_R_factor_gt           0.0815
_refine_ls_wR_factor_ref         0.2126
_refine_ls_wR_factor_gt          0.1986
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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
S1 S 0.60485(6) -0.07580(13) 0.82678(8) 0.0497(3) Uani 1 1 d . . . . .
F1 F 0.9750(5) -0.2693(13) 1.0847(7) 0.0821(11) Uani 0.461(3) 1 d . . P A 1
F2 F 0.9234(5) -0.2442(12) 1.2501(7) 0.0821(11) Uani 0.461(3) 1 d . . P A 1
F3 F 0.9658(5) -0.0193(11) 1.1738(7) 0.0821(11) Uani 0.461(3) 1 d . . P A 1
F1' F 0.9758(9) -0.286(2) 1.1342(12) 0.0821(11) Uani 0.250(3) 1 d . . P A 2
F2' F 0.9313(9) -0.170(2) 1.2625(14) 0.0821(11) Uani 0.250(3) 1 d . . P A 2
F3' F 0.9850(8) -0.048(2) 1.1320(12) 0.0821(11) Uani 0.250(3) 1 d . . P A 2
F1" F 0.9266(7) -0.2980(16) 1.2177(11) 0.0821(11) Uani 0.289(3) 1 d . . P A 3
F2" F 0.9464(7) -0.0259(19) 1.2217(10) 0.0821(11) Uani 0.289(3) 1 d . . P A 3
F3" F 0.9892(8) -0.1908(18) 1.1032(11) 0.0821(11) Uani 0.289(3) 1 d . . P A 3
O1 O 0.54287(18) -0.1567(4) 0.8741(3) 0.0703(9) Uani 1 1 d . . . . .
O2 O 0.6156(2) -0.1164(4) 0.7122(3) 0.0741(9) Uani 1 1 d . . . . .
O3 O 0.59225(16) 0.1186(4) 0.8248(2) 0.0574(7) Uani 1 1 d . . . . .
C1 C 0.8472(2) -0.1445(5) 1.0689(3) 0.0495(9) Uani 1 1 d . . . . .
C2 C 0.7767(2) -0.1990(5) 1.1032(3) 0.0545(10) Uani 1 1 d . . . . .
H2 H 0.7795 -0.2494 1.1758 0.065 Uiso 1 1 calc R U . . .
C3 C 0.7029(2) -0.1785(5) 1.0299(3) 0.0504(9) Uani 1 1 d . . . . .
H3 H 0.6556 -0.2163 1.0522 0.060 Uiso 1 1 calc R U . . .
C4 C 0.6987(2) -0.1021(4) 0.9233(3) 0.0411(8) Uani 1 1 d . . . . .
C5 C 0.7696(2) -0.0456(5) 0.8889(3) 0.0495(9) Uani 1 1 d . . . . .
H5 H 0.7667 0.0063 0.8168 0.059 Uiso 1 1 calc R U . . .
C6 C 0.8431(2) -0.0672(5) 0.9621(4) 0.0546(10) Uani 1 1 d . . . . .
H6 H 0.8905 -0.0297 0.9400 0.065 Uiso 1 1 calc R U . . .
C7 C 0.5643(3) 0.1976(6) 0.9239(4) 0.0651(12) Uani 1 1 d . . . . .
H7A H 0.5826 0.1324 0.9944 0.078 Uiso 1 1 calc R U . . .
H7B H 0.5052 0.2030 0.9089 0.078 Uiso 1 1 calc R U . . .
C8 C 0.6000(3) 0.3726(6) 0.9382(5) 0.0797(15) Uani 1 1 d . . . . .
H8A H 0.5836 0.4335 0.8653 0.096 Uiso 1 1 calc R U . . .
H8B H 0.5776 0.4316 0.9975 0.096 Uiso 1 1 calc R U . . .
C9 C 0.6915(3) 0.3741(5) 0.9718(4) 0.0600(11) Uani 1 1 d . . . . .
C10 C 0.7402(4) 0.4277(6) 0.8942(5) 0.0825(16) Uani 1 1 d . . . . .
H10 H 0.7162 0.4649 0.8199 0.099 Uiso 1 1 calc R U . . .
C11 C 0.8249(5) 0.4251(7) 0.9285(6) 0.096(2) Uani 1 1 d . . . . .
H11 H 0.8570 0.4606 0.8764 0.115 Uiso 1 1 calc R U . . .
C12 C 0.8608(4) 0.3725(8) 1.0351(6) 0.0920(18) Uani 1 1 d . . . . .
H12 H 0.9173 0.3729 1.0564 0.110 Uiso 1 1 calc R U . . .
C13 C 0.8157(3) 0.3188(6) 1.1120(5) 0.0788(14) Uani 1 1 d . . . . .
H13 H 0.8409 0.2814 1.1857 0.095 Uiso 1 1 calc R U . . .
C14 C 0.7305(3) 0.3202(5) 1.0797(4) 0.0624(11) Uani 1 1 d . . . . .
H14 H 0.6995 0.2834 1.1329 0.075 Uiso 1 1 calc R U . . .
C15 C 0.9283(3) -0.1676(6) 1.1484(5) 0.0712(12) 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
S1 O1 1.420(3) . ?
S1 O2 1.421(3) . ?
S1 O3 1.557(3) . ?
S1 C4 1.756(4) . ?
F1 C15 1.429(11) . ?
F2 C15 1.350(10) . ?
F3 C15 1.339(9) . ?
F1' C15 1.263(16) . ?
F2' C15 1.323(18) . ?
F3' C15 1.378(16) . ?
F1" C15 1.317(15) . ?
F2" C15 1.410(14) . ?
F3" C15 1.250(14) . ?
O3 C7 1.470(5) . ?
C1 C6 1.381(6) . ?
C1 C2 1.386(5) . ?
C1 C15 1.498(6) . ?
C2 C3 1.367(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.374(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.398(5) . ?
C5 C6 1.364(6) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.508(7) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.504(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C14 1.369(6) . ?
C9 C10 1.398(7) . ?
C10 C11 1.395(9) . ?
C10 H10 0.9300 . ?
C11 C12 1.339(9) . ?
C11 H11 0.9300 . ?
C12 C13 1.350(8) . ?
C12 H12 0.9300 . ?
C13 C14 1.401(7) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?

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 O2 120.03(19) . . ?
O1 S1 O3 110.29(18) . . ?
O2 S1 O3 104.63(19) . . ?
O1 S1 C4 108.94(18) . . ?
O2 S1 C4 108.41(18) . . ?
O3 S1 C4 103.22(15) . . ?
C7 O3 S1 118.3(3) . . ?
C6 C1 C2 120.3(4) . . ?
C6 C1 C15 119.6(4) . . ?
C2 C1 C15 120.1(4) . . ?
C3 C2 C1 119.8(4) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 120.1(3) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 120.4(3) . . ?
C3 C4 S1 121.0(3) . . ?
C5 C4 S1 118.6(3) . . ?
C6 C5 C4 119.3(3) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C1 120.2(3) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
O3 C7 C8 107.5(4) . . ?
O3 C7 H7A 110.2 . . ?
C8 C7 H7A 110.2 . . ?
O3 C7 H7B 110.2 . . ?
C8 C7 H7B 110.2 . . ?
H7A C7 H7B 108.5 . . ?
C9 C8 C7 113.3(4) . . ?
C9 C8 H8A 108.9 . . ?
C7 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
C7 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
C14 C9 C10 117.4(5) . . ?
C14 C9 C8 121.0(4) . . ?
C10 C9 C8 121.6(5) . . ?
C11 C10 C9 119.8(5) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C12 C11 C10 121.1(5) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 120.7(6) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C12 C13 C14 119.3(5) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C9 C14 C13 121.8(5) . . ?
C9 C14 H14 119.1 . . ?
C13 C14 H14 119.1 . . ?
F3" C15 F1" 105.1(9) . . ?
F1' C15 F2' 102.9(9) . . ?
F3 C15 F2 107.9(6) . . ?
F1' C15 F3' 91.4(11) . . ?
F2' C15 F3' 104.9(10) . . ?
F3" C15 F2" 106.1(8) . . ?
F1" C15 F2" 106.4(8) . . ?
F3 C15 F1 109.3(6) . . ?
F2 C15 F1 109.7(6) . . ?
F3" C15 C1 118.0(7) . . ?
F1' C15 C1 121.7(8) . . ?
F1" C15 C1 110.6(6) . . ?
F2' C15 C1 118.5(7) . . ?
F3 C15 C1 111.0(5) . . ?
F2 C15 C1 113.4(5) . . ?
F3' C15 C1 113.2(7) . . ?
F2" C15 C1 109.9(6) . . ?
F1 C15 C1 105.5(5) . . ?

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
O1 S1 O3 C7 38.5(3) . . . . ?
O2 S1 O3 C7 168.9(3) . . . . ?
C4 S1 O3 C7 -77.8(3) . . . . ?
C6 C1 C2 C3 1.1(6) . . . . ?
C15 C1 C2 C3 -179.6(4) . . . . ?
C1 C2 C3 C4 -0.8(6) . . . . ?
C2 C3 C4 C5 0.2(6) . . . . ?
C2 C3 C4 S1 179.4(3) . . . . ?
O1 S1 C4 C3 -5.0(4) . . . . ?
O2 S1 C4 C3 -137.2(3) . . . . ?
O3 S1 C4 C3 112.2(3) . . . . ?
O1 S1 C4 C5 174.2(3) . . . . ?
O2 S1 C4 C5 42.0(3) . . . . ?
O3 S1 C4 C5 -68.6(3) . . . . ?
C3 C4 C5 C6 0.1(5) . . . . ?
S1 C4 C5 C6 -179.1(3) . . . . ?
C4 C5 C6 C1 0.1(6) . . . . ?
C2 C1 C6 C5 -0.7(6) . . . . ?
C15 C1 C6 C5 179.9(4) . . . . ?
S1 O3 C7 C8 149.0(3) . . . . ?
O3 C7 C8 C9 -64.8(5) . . . . ?
C7 C8 C9 C14 -68.9(6) . . . . ?
C7 C8 C9 C10 110.1(5) . . . . ?
C14 C9 C10 C11 -0.2(7) . . . . ?
C8 C9 C10 C11 -179.2(4) . . . . ?
C9 C10 C11 C12 -0.2(8) . . . . ?
C10 C11 C12 C13 0.6(9) . . . . ?
C11 C12 C13 C14 -0.6(8) . . . . ?
C10 C9 C14 C13 0.2(6) . . . . ?
C8 C9 C14 C13 179.2(4) . . . . ?
C12 C13 C14 C9 0.2(7) . . . . ?
C6 C1 C15 F3" -32.3(10) . . . . ?
C2 C1 C15 F3" 148.4(8) . . . . ?
C6 C1 C15 F1' -80.1(11) . . . . ?
C2 C1 C15 F1' 100.6(11) . . . . ?
C6 C1 C15 F1" -153.4(7) . . . . ?
C2 C1 C15 F1" 27.3(8) . . . . ?
C6 C1 C15 F2' 150.5(9) . . . . ?
C2 C1 C15 F2' -28.8(11) . . . . ?
C6 C1 C15 F3 58.0(7) . . . . ?
C2 C1 C15 F3 -121.3(6) . . . . ?
C6 C1 C15 F2 179.7(5) . . . . ?
C2 C1 C15 F2 0.4(7) . . . . ?
C6 C1 C15 F3' 27.1(9) . . . . ?
C2 C1 C15 F3' -152.2(8) . . . . ?
C6 C1 C15 F2" 89.5(8) . . . . ?
C2 C1 C15 F2" -89.8(8) . . . . ?
C6 C1 C15 F1 -60.3(7) . . . . ?
C2 C1 C15 F1 120.4(6) . . . . ?

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
C3 H3 O2 0.93 2.49 3.245(5) 138.6 4_556
C7 H7B O2 0.97 2.65 3.448(5) 139.8 2_656

_refine_diff_density_max         0.372
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.066

####################################################################### 
# 
# 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_4a
_database_code_depnum_ccdc_archive 'CCDC 2337439'
loop_
_audit_author_name
_audit_author_address
'Rajesh Gonnade'
;CSIR NATIONAL CHEMICAL LABORATORY PUNE INDIA
India
;
_audit_update_record             
;
2024-03-02 deposited with the CCDC.	2024-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H13 Br O3 S'
_chemical_formula_weight         341.21

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'
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   7.5635(5)
_cell_length_b                   24.1053(16)
_cell_length_c                   8.0213(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.6860(10)
_cell_angle_gamma                90
_cell_volume                     1414.67(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3517
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      26.58

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    3.053
_shelx_estimated_absorpt_T_min   0.566
_shelx_estimated_absorpt_T_max   0.815
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.4219
_exptl_absorpt_correction_T_max  0.7470
_exptl_absorpt_process_details   SADABS,(BRUKER,2006)
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_source_type              'Incoatech I\mS HB'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            10556
_diffrn_reflns_av_unetI/netI     0.1720
_diffrn_reflns_av_R_equivalents  0.0793
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.910
_diffrn_reflns_theta_max         28.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.904
_diffrn_reflns_point_group_measured_fraction_full 0.904
_reflns_number_total             6162
_reflns_number_gt                4339
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.818
_reflns_Friedel_fraction_max     0.832
_reflns_Friedel_fraction_full    0.842

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

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL, Mercury 2020.20'
_computing_publication_material  'Bruker SHELXTL'
_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)] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'direct method'
_atom_sites_solution_secondary   'difference Fourier'
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.044(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1444 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.060(13)
_chemical_absolute_configuration .
_refine_ls_number_reflns         6162
_refine_ls_number_parameters     344
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0931
_refine_ls_R_factor_gt           0.0497
_refine_ls_wR_factor_ref         0.1596
_refine_ls_wR_factor_gt          0.1328
_refine_ls_goodness_of_fit_ref   0.940
_refine_ls_restrained_S_all      0.940
_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
Br1A Br 0.59234(13) 0.33377(5) 1.23692(13) 0.0805(4) Uani 1 1 d . . . . .
S1A S 0.1865(2) 0.45082(8) 0.5329(2) 0.0423(4) Uani 1 1 d . . . . .
O1A O 0.1882(8) 0.4160(3) 0.3892(7) 0.0598(15) Uani 1 1 d . . . . .
O2A O 0.0206(7) 0.4746(3) 0.5495(8) 0.0639(17) Uani 1 1 d . . . . .
O3A O 0.3148(7) 0.5020(2) 0.5347(6) 0.0466(12) Uani 1 1 d . . . . .
C1A C 0.4644(10) 0.3674(4) 1.0257(11) 0.0508(19) Uani 1 1 d . . . . .
C2A C 0.4795(10) 0.3436(4) 0.8755(12) 0.0523(18) Uani 1 1 d . . . . .
H2A H 0.549192 0.311712 0.876585 0.063 Uiso 1 1 calc R U . . .
C3A C 0.3889(10) 0.3678(4) 0.7225(10) 0.0480(17) Uani 1 1 d . . . . .
H3A H 0.392039 0.351486 0.618257 0.058 Uiso 1 1 calc R U . . .
C4A C 0.2930(8) 0.4167(3) 0.7245(8) 0.0369(14) Uani 1 1 d . . . . .
C5A C 0.2814(10) 0.4406(4) 0.8788(10) 0.0472(17) Uani 1 1 d . . . . .
H5A H 0.216397 0.473302 0.879022 0.057 Uiso 1 1 calc R U . . .
C6A C 0.3679(11) 0.4149(4) 1.0326(10) 0.0521(19) Uani 1 1 d . . . . .
H6A H 0.360434 0.429690 1.137677 0.063 Uiso 1 1 calc R U . . .
C7A C 0.4900(11) 0.4929(4) 0.4973(11) 0.0511(18) Uani 1 1 d . . . . .
H7AA H 0.478609 0.497559 0.374951 0.061 Uiso 1 1 calc R U . . .
H7AB H 0.531960 0.455473 0.529421 0.061 Uiso 1 1 calc R U . . .
C8A C 0.6244(11) 0.5340(4) 0.5977(10) 0.0513(18) Uani 1 1 d . . . . .
H8AA H 0.574890 0.571123 0.572875 0.062 Uiso 1 1 calc R U . . .
H8AB H 0.736279 0.532001 0.559731 0.062 Uiso 1 1 calc R U . . .
C9A C 0.6693(9) 0.5245(4) 0.7901(10) 0.0428(16) Uani 1 1 d . . . . .
C10A C 0.6072(10) 0.5621(4) 0.8954(11) 0.0505(19) Uani 1 1 d . . . . .
H10A H 0.537334 0.592517 0.846916 0.061 Uiso 1 1 calc R U . . .
C11A C 0.6502(12) 0.5539(5) 1.0720(12) 0.059(2) Uani 1 1 d . . . . .
H11A H 0.605123 0.578078 1.141585 0.071 Uiso 1 1 calc R U . . .
C12A C 0.7588(11) 0.5101(5) 1.1449(12) 0.060(2) Uani 1 1 d . . . . .
H12A H 0.791837 0.505762 1.263957 0.072 Uiso 1 1 calc R U . . .
C13A C 0.8183(12) 0.4731(4) 1.0425(12) 0.059(2) Uani 1 1 d . . . . .
H13A H 0.888470 0.442761 1.091153 0.070 Uiso 1 1 calc R U . . .
C14A C 0.7734(11) 0.4811(4) 0.8644(12) 0.0516(18) Uani 1 1 d . . . . .
H14A H 0.815829 0.456005 0.795287 0.062 Uiso 1 1 calc R U . . .
Br1B Br -0.11975(13) 0.32407(5) -0.35477(13) 0.0784(4) Uani 1 1 d . . . . .
S1B S 0.2907(2) 0.21296(8) 0.3585(2) 0.0404(4) Uani 1 1 d . . . . .
O1B O 0.2817(9) 0.2484(3) 0.4971(7) 0.0582(14) Uani 1 1 d . . . . .
O2B O 0.4611(7) 0.1912(3) 0.3454(8) 0.0559(14) Uani 1 1 d . . . . .
O3B O 0.1706(7) 0.1601(2) 0.3580(8) 0.0507(13) Uani 1 1 d . . . . .
C1B C 0.0052(8) 0.2925(4) -0.1427(10) 0.0452(17) Uani 1 1 d . . . . .
C2B C 0.1051(11) 0.2443(4) -0.1426(10) 0.054(2) Uani 1 1 d . . . . .
H2B H 0.111075 0.227959 -0.246055 0.065 Uiso 1 1 calc R U . . .
C3B C 0.1947(10) 0.2210(4) 0.0110(10) 0.0485(17) Uani 1 1 d . . . . .
H3B H 0.264430 0.189163 0.012948 0.058 Uiso 1 1 calc R U . . .
C4B C 0.1810(9) 0.2453(3) 0.1635(9) 0.0384(14) Uani 1 1 d . . . . .
C5B C 0.0832(10) 0.2932(3) 0.1644(10) 0.0483(18) Uani 1 1 d . . . . .
H5B H 0.077070 0.309416 0.268000 0.058 Uiso 1 1 calc R U . . .
C6B C -0.0065(11) 0.3171(4) 0.0085(11) 0.0543(19) Uani 1 1 d . . . . .
H6B H -0.073841 0.349461 0.006476 0.065 Uiso 1 1 calc R U . . .
C7B C -0.0098(12) 0.1672(5) 0.3912(12) 0.065(3) Uani 1 1 d . . . . .
H7BA H -0.057527 0.203784 0.354711 0.078 Uiso 1 1 calc R U . . .
H7BB H -0.000849 0.163396 0.513482 0.078 Uiso 1 1 calc R U . . .
C8B C -0.1345(12) 0.1233(5) 0.2917(12) 0.058(2) Uani 1 1 d . . . . .
H8BA H -0.076439 0.087376 0.318586 0.070 Uiso 1 1 calc R U . . .
H8BB H -0.246591 0.122850 0.329501 0.070 Uiso 1 1 calc R U . . .
C9B C -0.1819(9) 0.1314(3) 0.1000(10) 0.0439(16) Uani 1 1 d . . . . .
C10B C -0.2993(12) 0.1745(4) 0.0234(12) 0.0506(19) Uani 1 1 d . . . . .
H10B H -0.343850 0.198847 0.092954 0.061 Uiso 1 1 calc R U . . .
C11B C -0.3497(13) 0.1815(4) -0.1521(13) 0.062(2) Uani 1 1 d . . . . .
H11B H -0.428187 0.210218 -0.199869 0.075 Uiso 1 1 calc R U . . .
C12B C -0.2860(12) 0.1468(5) -0.2563(12) 0.062(2) Uani 1 1 d . . . . .
H12B H -0.319481 0.151672 -0.375205 0.075 Uiso 1 1 calc R U . . .
C13B C -0.1682(13) 0.1032(5) -0.1819(13) 0.072(3) Uani 1 1 d . . . . .
H13B H -0.124161 0.078889 -0.252007 0.086 Uiso 1 1 calc R U . . .
C14B C -0.1188(10) 0.0965(4) -0.0084(12) 0.058(2) Uani 1 1 d . . . . .
H14B H -0.040271 0.067684 0.038670 0.070 Uiso 1 1 calc R 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
Br1A C1A 1.905(8) . ?
S1A O2A 1.416(6) . ?
S1A O1A 1.429(6) . ?
S1A O3A 1.568(6) . ?
S1A C4A 1.749(7) . ?
O3A C7A 1.448(9) . ?
C1A C2A 1.365(12) . ?
C1A C6A 1.368(13) . ?
C2A C3A 1.375(12) . ?
C2A H2A 0.9300 . ?
C3A C4A 1.387(11) . ?
C3A H3A 0.9300 . ?
C4A C5A 1.387(10) . ?
C5A C6A 1.387(11) . ?
C5A H5A 0.9300 . ?
C6A H6A 0.9300 . ?
C7A C8A 1.500(12) . ?
C7A H7AA 0.9700 . ?
C7A H7AB 0.9700 . ?
C8A C9A 1.512(10) . ?
C8A H8AA 0.9700 . ?
C8A H8AB 0.9700 . ?
C9A C14A 1.354(12) . ?
C9A C10A 1.398(11) . ?
C10A C11A 1.385(13) . ?
C10A H10A 0.9300 . ?
C11A C12A 1.372(14) . ?
C11A H11A 0.9300 . ?
C12A C13A 1.364(14) . ?
C12A H12A 0.9300 . ?
C13A C14A 1.395(13) . ?
C13A H13A 0.9300 . ?
C14A H14A 0.9300 . ?
Br1B C1B 1.885(8) . ?
S1B O1B 1.418(6) . ?
S1B O2B 1.419(5) . ?
S1B O3B 1.564(6) . ?
S1B C4B 1.756(8) . ?
O3B C7B 1.465(10) . ?
C1B C6B 1.373(12) . ?
C1B C2B 1.385(13) . ?
C2B C3B 1.367(12) . ?
C2B H2B 0.9300 . ?
C3B C4B 1.383(10) . ?
C3B H3B 0.9300 . ?
C4B C5B 1.373(11) . ?
C5B C6B 1.387(12) . ?
C5B H5B 0.9300 . ?
C6B H6B 0.9300 . ?
C7B C8B 1.506(14) . ?
C7B H7BA 0.9700 . ?
C7B H7BB 0.9700 . ?
C8B C9B 1.500(12) . ?
C8B H8BA 0.9700 . ?
C8B H8BB 0.9700 . ?
C9B C14B 1.379(12) . ?
C9B C10B 1.403(13) . ?
C10B C11B 1.372(14) . ?
C10B H10B 0.9300 . ?
C11B C12B 1.354(14) . ?
C11B H11B 0.9300 . ?
C12B C13B 1.409(16) . ?
C12B H12B 0.9300 . ?
C13B C14B 1.356(14) . ?
C13B H13B 0.9300 . ?
C14B H14B 0.9300 . ?

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
O2A S1A O1A 120.2(4) . . ?
O2A S1A O3A 104.0(4) . . ?
O1A S1A O3A 109.7(3) . . ?
O2A S1A C4A 109.2(3) . . ?
O1A S1A C4A 109.7(4) . . ?
O3A S1A C4A 102.5(3) . . ?
C7A O3A S1A 118.4(5) . . ?
C2A C1A C6A 123.5(8) . . ?
C2A C1A Br1A 118.0(7) . . ?
C6A C1A Br1A 118.5(6) . . ?
C1A C2A C3A 118.4(7) . . ?
C1A C2A H2A 120.8 . . ?
C3A C2A H2A 120.8 . . ?
C2A C3A C4A 119.7(7) . . ?
C2A C3A H3A 120.2 . . ?
C4A C3A H3A 120.2 . . ?
C3A C4A C5A 121.0(7) . . ?
C3A C4A S1A 121.0(5) . . ?
C5A C4A S1A 118.0(6) . . ?
C6A C5A C4A 119.1(8) . . ?
C6A C5A H5A 120.4 . . ?
C4A C5A H5A 120.4 . . ?
C1A C6A C5A 118.3(7) . . ?
C1A C6A H6A 120.8 . . ?
C5A C6A H6A 120.8 . . ?
O3A C7A C8A 108.7(7) . . ?
O3A C7A H7AA 109.9 . . ?
C8A C7A H7AA 109.9 . . ?
O3A C7A H7AB 109.9 . . ?
C8A C7A H7AB 109.9 . . ?
H7AA C7A H7AB 108.3 . . ?
C7A C8A C9A 113.1(7) . . ?
C7A C8A H8AA 109.0 . . ?
C9A C8A H8AA 109.0 . . ?
C7A C8A H8AB 109.0 . . ?
C9A C8A H8AB 109.0 . . ?
H8AA C8A H8AB 107.8 . . ?
C14A C9A C10A 118.8(7) . . ?
C14A C9A C8A 121.5(7) . . ?
C10A C9A C8A 119.7(7) . . ?
C11A C10A C9A 119.8(8) . . ?
C11A C10A H10A 120.1 . . ?
C9A C10A H10A 120.1 . . ?
C12A C11A C10A 120.3(8) . . ?
C12A C11A H11A 119.8 . . ?
C10A C11A H11A 119.8 . . ?
C13A C12A C11A 119.9(8) . . ?
C13A C12A H12A 120.0 . . ?
C11A C12A H12A 120.0 . . ?
C12A C13A C14A 119.7(8) . . ?
C12A C13A H13A 120.2 . . ?
C14A C13A H13A 120.2 . . ?
C9A C14A C13A 121.3(8) . . ?
C9A C14A H14A 119.3 . . ?
C13A C14A H14A 119.3 . . ?
O1B S1B O2B 120.4(4) . . ?
O1B S1B O3B 110.5(3) . . ?
O2B S1B O3B 103.7(4) . . ?
O1B S1B C4B 109.0(4) . . ?
O2B S1B C4B 109.3(3) . . ?
O3B S1B C4B 102.5(3) . . ?
C7B O3B S1B 118.1(6) . . ?
C6B C1B C2B 121.3(8) . . ?
C6B C1B Br1B 119.5(7) . . ?
C2B C1B Br1B 119.2(6) . . ?
C3B C2B C1B 119.3(7) . . ?
C3B C2B H2B 120.3 . . ?
C1B C2B H2B 120.3 . . ?
C2B C3B C4B 119.5(8) . . ?
C2B C3B H3B 120.2 . . ?
C4B C3B H3B 120.2 . . ?
C5B C4B C3B 121.4(7) . . ?
C5B C4B S1B 120.2(5) . . ?
C3B C4B S1B 118.4(6) . . ?
C4B C5B C6B 119.1(7) . . ?
C4B C5B H5B 120.5 . . ?
C6B C5B H5B 120.5 . . ?
C1B C6B C5B 119.4(8) . . ?
C1B C6B H6B 120.3 . . ?
C5B C6B H6B 120.3 . . ?
O3B C7B C8B 108.0(8) . . ?
O3B C7B H7BA 110.1 . . ?
C8B C7B H7BA 110.1 . . ?
O3B C7B H7BB 110.1 . . ?
C8B C7B H7BB 110.1 . . ?
H7BA C7B H7BB 108.4 . . ?
C9B C8B C7B 114.0(8) . . ?
C9B C8B H8BA 108.7 . . ?
C7B C8B H8BA 108.7 . . ?
C9B C8B H8BB 108.7 . . ?
C7B C8B H8BB 108.7 . . ?
H8BA C8B H8BB 107.6 . . ?
C14B C9B C10B 117.2(8) . . ?
C14B C9B C8B 122.4(8) . . ?
C10B C9B C8B 120.4(8) . . ?
C11B C10B C9B 121.3(8) . . ?
C11B C10B H10B 119.3 . . ?
C9B C10B H10B 119.3 . . ?
C12B C11B C10B 120.5(9) . . ?
C12B C11B H11B 119.7 . . ?
C10B C11B H11B 119.7 . . ?
C11B C12B C13B 119.0(9) . . ?
C11B C12B H12B 120.5 . . ?
C13B C12B H12B 120.5 . . ?
C14B C13B C12B 120.2(8) . . ?
C14B C13B H13B 119.9 . . ?
C12B C13B H13B 119.9 . . ?
C13B C14B C9B 121.7(8) . . ?
C13B C14B H14B 119.1 . . ?
C9B C14B H14B 119.1 . . ?

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
O2A S1A O3A C7A -172.1(5) . . . . ?
O1A S1A O3A C7A -42.2(6) . . . . ?
C4A S1A O3A C7A 74.2(5) . . . . ?
C6A C1A C2A C3A -1.7(12) . . . . ?
Br1A C1A C2A C3A -179.4(6) . . . . ?
C1A C2A C3A C4A 3.1(12) . . . . ?
C2A C3A C4A C5A -2.4(11) . . . . ?
C2A C3A C4A S1A 176.5(6) . . . . ?
O2A S1A C4A C3A 144.0(6) . . . . ?
O1A S1A C4A C3A 10.3(7) . . . . ?
O3A S1A C4A C3A -106.2(6) . . . . ?
O2A S1A C4A C5A -37.1(7) . . . . ?
O1A S1A C4A C5A -170.8(6) . . . . ?
O3A S1A C4A C5A 72.7(6) . . . . ?
C3A C4A C5A C6A 0.2(11) . . . . ?
S1A C4A C5A C6A -178.7(6) . . . . ?
C2A C1A C6A C5A -0.4(13) . . . . ?
Br1A C1A C6A C5A 177.3(6) . . . . ?
C4A C5A C6A C1A 1.1(12) . . . . ?
S1A O3A C7A C8A -148.0(6) . . . . ?
O3A C7A C8A C9A 67.4(9) . . . . ?
C7A C8A C9A C14A 72.1(9) . . . . ?
C7A C8A C9A C10A -109.9(9) . . . . ?
C14A C9A C10A C11A -1.1(12) . . . . ?
C8A C9A C10A C11A -179.1(8) . . . . ?
C9A C10A C11A C12A 2.4(13) . . . . ?
C10A C11A C12A C13A -2.9(13) . . . . ?
C11A C12A C13A C14A 2.2(13) . . . . ?
C10A C9A C14A C13A 0.4(12) . . . . ?
C8A C9A C14A C13A 178.4(8) . . . . ?
C12A C13A C14A C9A -1.0(13) . . . . ?
O1B S1B O3B C7B 42.4(7) . . . . ?
O2B S1B O3B C7B 172.7(6) . . . . ?
C4B S1B O3B C7B -73.6(6) . . . . ?
C6B C1B C2B C3B -0.4(12) . . . . ?
Br1B C1B C2B C3B -179.5(6) . . . . ?
C1B C2B C3B C4B 1.4(12) . . . . ?
C2B C3B C4B C5B -1.8(11) . . . . ?
C2B C3B C4B S1B 177.7(6) . . . . ?
O1B S1B C4B C5B -8.9(7) . . . . ?
O2B S1B C4B C5B -142.3(6) . . . . ?
O3B S1B C4B C5B 108.2(6) . . . . ?
O1B S1B C4B C3B 171.6(6) . . . . ?
O2B S1B C4B C3B 38.2(7) . . . . ?
O3B S1B C4B C3B -71.3(6) . . . . ?
C3B C4B C5B C6B 1.3(11) . . . . ?
S1B C4B C5B C6B -178.2(6) . . . . ?
C2B C1B C6B C5B -0.1(12) . . . . ?
Br1B C1B C6B C5B 178.9(6) . . . . ?
C4B C5B C6B C1B -0.3(12) . . . . ?
S1B O3B C7B C8B 148.3(7) . . . . ?
O3B C7B C8B C9B -69.4(11) . . . . ?
C7B C8B C9B C14B 110.8(10) . . . . ?
C7B C8B C9B C10B -71.3(10) . . . . ?
C14B C9B C10B C11B 0.3(11) . . . . ?
C8B C9B C10B C11B -177.6(8) . . . . ?
C9B C10B C11B C12B -0.4(13) . . . . ?
C10B C11B C12B C13B 0.5(14) . . . . ?
C11B C12B C13B C14B -0.5(15) . . . . ?
C12B C13B C14B C9B 0.4(15) . . . . ?
C10B C9B C14B C13B -0.3(12) . . . . ?
C8B C9B C14B C13B 177.6(9) . . . . ?

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
_geom_hbond_publ_flag
C8A H8AB O2A 0.97 2.58 3.431(10) 147.0 1_655 yes

_refine_diff_density_max         0.510
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.086

####################################################################### 
# 
# 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_3a
_database_code_depnum_ccdc_archive 'CCDC 2337438'
loop_
_audit_author_name
_audit_author_address
'Rajesh Gonnade'
;CSIR NATIONAL CHEMICAL LABORATORY PUNE INDIA
India
;
_audit_update_record             
;
2024-03-02 deposited with the CCDC.	2024-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H13 Cl O3 S'
_chemical_formula_sum            'C14 H13 Cl O3 S'
_chemical_formula_weight         296.75

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'
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'
Cl Cl 0.1484 0.1585 '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                   15.5325(8)
_cell_length_b                   7.7124(3)
_cell_length_c                   11.7108(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.106(4)
_cell_angle_gamma                90
_cell_volume                     1381.10(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    890
_cell_measurement_theta_min      2.96
_cell_measurement_theta_max      32.98

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.428
_shelx_estimated_absorpt_T_min   0.904
_shelx_estimated_absorpt_T_max   0.963
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.6563
_exptl_absorpt_correction_T_max  0.7474
_exptl_absorpt_process_details   SADABS,(BRUKER,2006)
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_source_type              'Incoatech I\mS HB'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            12254
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.664
_diffrn_reflns_theta_max         27.993
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             3292
_reflns_number_gt                3000
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL, Mercury 2020.20'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0437P)²+0.5022P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'direct method'
_atom_sites_solution_secondary   'difference Fourier'
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3292
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_ref         0.0882
_refine_ls_wR_factor_gt          0.0852
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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
Cl1 Cl 0.45928(3) 0.32292(7) 0.67270(4) 0.05569(14) Uani 1 1 d . . . . .
S1 S 0.11049(2) 0.43391(4) 0.32657(3) 0.02786(10) Uani 1 1 d . . . . .
O1 O 0.04174(7) 0.35392(14) 0.37278(10) 0.0411(3) Uani 1 1 d . . . . .
O2 O 0.12395(7) 0.38990(15) 0.21178(8) 0.0410(3) Uani 1 1 d . . . . .
O3 O 0.09876(6) 0.63489(12) 0.32308(8) 0.0308(2) Uani 1 1 d . . . . .
C1 C 0.36206(9) 0.35394(18) 0.57623(12) 0.0323(3) Uani 1 1 d . . . . .
C2 C 0.36357(9) 0.42658(18) 0.46741(12) 0.0329(3) Uani 1 1 d . . . . .
H2 H 0.416459 0.457521 0.446238 0.039 Uiso 1 1 calc R U . . .
C3 C 0.28607(8) 0.45212(16) 0.39153(11) 0.0281(3) Uani 1 1 d . . . . .
H3 H 0.285975 0.501187 0.318967 0.034 Uiso 1 1 calc R U . . .
C4 C 0.20838(8) 0.40351(15) 0.42517(10) 0.0240(2) Uani 1 1 d . . . . .
C5 C 0.20754(9) 0.33086(16) 0.53397(11) 0.0302(3) Uani 1 1 d . . . . .
H5 H 0.154774 0.298945 0.555118 0.036 Uiso 1 1 calc R U . . .
C6 C 0.28534(10) 0.30617(17) 0.61068(12) 0.0332(3) Uani 1 1 d . . . . .
H6 H 0.285580 0.258439 0.683662 0.040 Uiso 1 1 calc R U . . .
C7 C 0.06937(9) 0.71709(19) 0.42345(12) 0.0350(3) Uani 1 1 d . . . . .
H7A H 0.087546 0.648113 0.492752 0.042 Uiso 1 1 calc R U . . .
H7B H 0.006115 0.726410 0.409704 0.042 Uiso 1 1 calc R U . . .
C8 C 0.11017(11) 0.8945(2) 0.43860(15) 0.0431(3) Uani 1 1 d . . . . .
H8A H 0.094128 0.959164 0.366958 0.052 Uiso 1 1 calc R U . . .
H8B H 0.086884 0.955913 0.498778 0.052 Uiso 1 1 calc R U . . .
C9 C 0.20769(10) 0.88826(16) 0.47025(12) 0.0335(3) Uani 1 1 d . . . . .
C10 C 0.24794(10) 0.82722(18) 0.57951(12) 0.0352(3) Uani 1 1 d . . . . .
H10 H 0.213471 0.791343 0.632496 0.042 Uiso 1 1 calc R U . . .
C11 C 0.33763(10) 0.8196(2) 0.60957(14) 0.0409(3) Uani 1 1 d . . . . .
H11 H 0.363498 0.778338 0.682144 0.049 Uiso 1 1 calc R U . . .
C12 C 0.38910(11) 0.8738(2) 0.53081(16) 0.0467(4) Uani 1 1 d . . . . .
H12 H 0.449731 0.869749 0.550600 0.056 Uiso 1 1 calc R U . . .
C13 C 0.35004(12) 0.9340(2) 0.42254(16) 0.0491(4) Uani 1 1 d . . . . .
H13 H 0.384715 0.970161 0.369874 0.059 Uiso 1 1 calc R U . . .
C14 C 0.26025(12) 0.94073(19) 0.39225(14) 0.0423(3) Uani 1 1 d . . . . .
H14 H 0.234758 0.980645 0.319179 0.051 Uiso 1 1 calc R 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
Cl1 C1 1.7365(14) . ?
S1 O1 1.4201(10) . ?
S1 O2 1.4368(10) . ?
S1 O3 1.5604(10) . ?
S1 C4 1.7561(13) . ?
O3 C7 1.4766(15) . ?
C1 C6 1.374(2) . ?
C1 C2 1.3959(19) . ?
C2 C3 1.3791(19) . ?
C2 H2 0.9300 . ?
C3 C4 1.3851(16) . ?
C3 H3 0.9300 . ?
C4 C5 1.3941(17) . ?
C5 C6 1.387(2) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.506(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.496(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C14 1.388(2) . ?
C9 C10 1.403(2) . ?
C10 C11 1.377(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.387(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.386(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.378(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?

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 O2 119.77(7) . . ?
O1 S1 O3 110.45(6) . . ?
O2 S1 O3 104.22(6) . . ?
O1 S1 C4 108.28(6) . . ?
O2 S1 C4 109.41(6) . . ?
O3 S1 C4 103.50(5) . . ?
C7 O3 S1 117.17(8) . . ?
C6 C1 C2 122.01(13) . . ?
C6 C1 Cl1 118.17(11) . . ?
C2 C1 Cl1 119.82(11) . . ?
C3 C2 C1 119.54(12) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 118.91(12) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C3 C4 C5 121.13(12) . . ?
C3 C4 S1 118.28(9) . . ?
C5 C4 S1 120.58(10) . . ?
C6 C5 C4 120.03(12) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C1 C6 C5 118.37(12) . . ?
C1 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
O3 C7 C8 107.55(11) . . ?
O3 C7 H7A 110.2 . . ?
C8 C7 H7A 110.2 . . ?
O3 C7 H7B 110.2 . . ?
C8 C7 H7B 110.2 . . ?
H7A C7 H7B 108.5 . . ?
C9 C8 C7 112.75(12) . . ?
C9 C8 H8A 109.0 . . ?
C7 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
C7 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C14 C9 C10 118.59(14) . . ?
C14 C9 C8 120.97(14) . . ?
C10 C9 C8 120.44(13) . . ?
C11 C10 C9 121.10(14) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C12 119.50(15) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C13 C12 C11 119.90(16) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C14 C13 C12 120.58(15) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C9 120.34(15) . . ?
C13 C14 H14 119.8 . . ?
C9 C14 H14 119.8 . . ?

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
O1 S1 O3 C7 40.43(11) . . . . ?
O2 S1 O3 C7 170.30(9) . . . . ?
C4 S1 O3 C7 -75.28(10) . . . . ?
C6 C1 C2 C3 0.1(2) . . . . ?
Cl1 C1 C2 C3 -179.50(10) . . . . ?
C1 C2 C3 C4 -0.49(19) . . . . ?
C2 C3 C4 C5 0.42(18) . . . . ?
C2 C3 C4 S1 -179.03(10) . . . . ?
O1 S1 C4 C3 172.09(10) . . . . ?
O2 S1 C4 C3 39.97(11) . . . . ?
O3 S1 C4 C3 -70.67(10) . . . . ?
O1 S1 C4 C5 -7.36(12) . . . . ?
O2 S1 C4 C5 -139.49(11) . . . . ?
O3 S1 C4 C5 109.88(10) . . . . ?
C3 C4 C5 C6 0.02(19) . . . . ?
S1 C4 C5 C6 179.45(10) . . . . ?
C2 C1 C6 C5 0.3(2) . . . . ?
Cl1 C1 C6 C5 179.94(10) . . . . ?
C4 C5 C6 C1 -0.37(19) . . . . ?
S1 O3 C7 C8 147.76(10) . . . . ?
O3 C7 C8 C9 -64.80(16) . . . . ?
C7 C8 C9 C14 110.17(16) . . . . ?
C7 C8 C9 C10 -69.19(17) . . . . ?
C14 C9 C10 C11 0.2(2) . . . . ?
C8 C9 C10 C11 179.55(13) . . . . ?
C9 C10 C11 C12 0.3(2) . . . . ?
C10 C11 C12 C13 -0.4(2) . . . . ?
C11 C12 C13 C14 0.1(2) . . . . ?
C12 C13 C14 C9 0.4(2) . . . . ?
C10 C9 C14 C13 -0.5(2) . . . . ?
C8 C9 C14 C13 -179.91(14) . . . . ?

_refine_diff_density_max         0.362
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_1b
_database_code_depnum_ccdc_archive 'CCDC 2337441'
loop_
_audit_author_name
_audit_author_address
'Rajesh Gonnade'
;CSIR NATIONAL CHEMICAL LABORATORY PUNE INDIA
India
;
_audit_update_record             
;
2024-03-02 deposited with the CCDC.	2024-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H14 F3 N O2 S'
_chemical_formula_sum            'C15 H14 F3 N O2 S'
_chemical_formula_weight         329.33

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'
F F 0.0171 0.0103 '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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   10.1905(6)
_cell_length_b                   26.3756(19)
_cell_length_c                   11.0620(8)
_cell_angle_alpha                90
_cell_angle_beta                 94.342(2)
_cell_angle_gamma                90
_cell_volume                     2964.7(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9892
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      32.97

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_F_000             1360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.257
_shelx_estimated_absorpt_T_min   0.941
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.6216
_exptl_absorpt_correction_T_max  0.7466
_exptl_absorpt_process_details   'SADABS,(Bruker, 2006)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_source_type              'Incoatech I\mS HB'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            42830
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.407
_diffrn_reflns_theta_max         27.994
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_point_group_measured_fraction_full 0.946
_reflns_number_total             13377
_reflns_number_gt                11918
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.847
_reflns_Friedel_fraction_max     0.876
_reflns_Friedel_fraction_full    0.901

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0540P)²+5.9410P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'direct method'
_atom_sites_solution_secondary   'difference Fourier'
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.48(14)
_chemical_absolute_configuration .
_refine_ls_number_reflns         13377
_refine_ls_number_parameters     810
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0559
_refine_ls_wR_factor_ref         0.1585
_refine_ls_wR_factor_gt          0.1515
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.049
_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
S1A S 0.00783(14) 0.24558(6) 0.51040(12) 0.0206(3) Uani 1 1 d . . . . .
F1A F 0.1203(5) 0.40496(19) 0.9786(3) 0.0373(10) Uani 1 1 d . . . . .
F2A F 0.0896(5) 0.45666(19) 0.8282(4) 0.0409(11) Uani 1 1 d . . . . .
F3A F 0.2839(4) 0.4242(2) 0.8739(4) 0.0400(10) Uani 1 1 d . . . . .
O1A O -0.1268(4) 0.2313(2) 0.5265(4) 0.0271(10) Uani 1 1 d . . . . .
O2A O 0.0430(4) 0.2621(2) 0.3931(3) 0.0259(10) Uani 1 1 d . . . . .
N1A N 0.0998(5) 0.1977(2) 0.5492(5) 0.0208(11) Uani 1 1 d D . . . .
H1NA H 0.182(4) 0.208(3) 0.549(7) 0.05(2) Uiso 1 1 d D . . . .
C1A C 0.1156(6) 0.3700(3) 0.7782(5) 0.0217(13) Uani 1 1 d . . . . .
C2A C 0.0186(7) 0.3370(3) 0.8044(5) 0.0256(14) Uani 1 1 d . . . . .
H2A H -0.024027 0.340075 0.877476 0.031 Uiso 1 1 calc R U . . .
C3A C -0.0162(6) 0.2988(3) 0.7212(5) 0.0202(12) Uani 1 1 d . . . . .
H3A H -0.084519 0.275550 0.735353 0.024 Uiso 1 1 calc R U . . .
C4A C 0.0523(7) 0.2954(3) 0.6157(5) 0.0212(13) Uani 1 1 d . . . . .
C5A C 0.1538(6) 0.3286(3) 0.5928(5) 0.0218(13) Uani 1 1 d . . . . .
H5A H 0.197032 0.325619 0.520023 0.026 Uiso 1 1 calc R U . . .
C6A C 0.1918(6) 0.3659(3) 0.6763(5) 0.0241(14) Uani 1 1 d . . . . .
H6A H 0.264655 0.387506 0.666086 0.029 Uiso 1 1 calc R U . . .
C7A C 0.0789(6) 0.1703(3) 0.6612(5) 0.0209(12) Uani 1 1 d . U . . .
H7A H -0.015987 0.163045 0.664835 0.025 Uiso 1 1 calc R U . . .
H8B H 0.107886 0.191624 0.731875 0.025 Uiso 1 1 calc R U . . .
C8A C 0.1552(5) 0.1213(2) 0.6663(5) 0.0170(11) Uani 1 1 d . U . . .
H8A H 0.129048 0.101074 0.593083 0.020 Uiso 1 1 calc R U . . .
H9B H 0.250178 0.129017 0.665527 0.020 Uiso 1 1 calc R U . . .
C9A C 0.1330(6) 0.0903(3) 0.7772(5) 0.0219(12) Uani 1 1 d . . . . .
C10A C 0.1856(6) 0.1048(3) 0.8887(5) 0.0288(13) Uani 1 1 d . . . . .
H10A H 0.237004 0.134879 0.896378 0.035 Uiso 1 1 calc R U . . .
C11A C 0.1649(6) 0.0760(3) 0.9926(5) 0.0320(14) Uani 1 1 d . . . . .
H11A H 0.203582 0.085953 1.069827 0.038 Uiso 1 1 calc R U . . .
C12A C 0.0877(8) 0.0331(3) 0.9809(7) 0.0394(19) Uani 1 1 d . . . . .
H12A H 0.072615 0.013318 1.050246 0.047 Uiso 1 1 calc R U . . .
C13A C 0.0326(7) 0.0189(3) 0.8687(6) 0.0351(14) Uani 1 1 d . . . . .
H13A H -0.021543 -0.010393 0.861098 0.042 Uiso 1 1 calc R U . . .
C14A C 0.0551(6) 0.0470(2) 0.7668(5) 0.0279(12) Uani 1 1 d . . . . .
H14A H 0.017435 0.036643 0.689563 0.034 Uiso 1 1 calc R U . . .
C15A C 0.1525(7) 0.4140(3) 0.8672(6) 0.0264(14) Uani 1 1 d . . . . .
S1B S 0.50874(13) 0.24479(6) 0.52947(12) 0.0203(3) Uani 1 1 d . . . . .
F1B F 0.6419(5) 0.4112(2) 0.9770(4) 0.0444(12) Uani 1 1 d . . . . .
F2B F 0.6193(6) 0.4609(2) 0.8250(5) 0.0581(15) Uani 1 1 d . . . . .
F3B F 0.8067(4) 0.4248(2) 0.8726(4) 0.0494(13) Uani 1 1 d . . . . .
O1B O 0.3758(4) 0.2306(2) 0.5518(4) 0.0281(10) Uani 1 1 d . . . . .
O2B O 0.5389(4) 0.2586(2) 0.4088(4) 0.0246(10) Uani 1 1 d . . . . .
N1B N 0.6028(5) 0.1982(2) 0.5717(4) 0.0203(11) Uani 1 1 d D . . . .
H1NB H 0.688(3) 0.205(3) 0.579(7) 0.04(2) Uiso 1 1 d D . . . .
C1B C 0.6322(7) 0.3739(3) 0.7793(5) 0.0247(14) Uani 1 1 d . . . . .
C2B C 0.5289(7) 0.3443(3) 0.8086(5) 0.0254(14) Uani 1 1 d . . . . .
H17 H 0.486470 0.350386 0.880704 0.030 Uiso 1 1 calc R U . . .
C3B C 0.4869(6) 0.3047(3) 0.7301(5) 0.0191(12) Uani 1 1 d . . . . .
H18 H 0.414014 0.283994 0.746121 0.023 Uiso 1 1 calc R U . . .
C4B C 0.5571(6) 0.2969(2) 0.6267(5) 0.0172(12) Uani 1 1 d . . . . .
C5B C 0.6622(6) 0.3270(3) 0.5993(5) 0.0187(13) Uani 1 1 d . . . . .
H5B H 0.704348 0.321403 0.526733 0.022 Uiso 1 1 calc R U . . .
C6B C 0.7058(5) 0.3656(3) 0.6791(5) 0.0167(11) Uani 1 1 d . . . . .
H6B H 0.781656 0.385155 0.666106 0.020 Uiso 1 1 calc R U . . .
C7B C 0.5869(6) 0.1727(3) 0.6874(5) 0.0214(12) Uani 1 1 d . . . . .
H8C H 0.492143 0.167664 0.698106 0.026 Uiso 1 1 calc R U . . .
H8D H 0.624717 0.193907 0.755157 0.026 Uiso 1 1 calc R U . . .
C8B C 0.6561(5) 0.1218(3) 0.6889(5) 0.0217(13) Uani 1 1 d . . . . .
H9C H 0.751906 0.127391 0.686203 0.026 Uiso 1 1 calc R U . . .
H9D H 0.625029 0.102459 0.615600 0.026 Uiso 1 1 calc R U . . .
C9B C 0.6316(6) 0.0906(3) 0.8014(6) 0.0234(13) Uani 1 1 d . . . . .
C10B C 0.5116(6) 0.0662(3) 0.8069(6) 0.0322(13) Uani 1 1 d . . . . .
H10B H 0.445602 0.070345 0.742279 0.039 Uiso 1 1 calc R U . . .
C11B C 0.4860(7) 0.0359(3) 0.9042(6) 0.0363(14) Uani 1 1 d . . . . .
H11B H 0.402954 0.019718 0.906203 0.044 Uiso 1 1 calc R U . . .
C12B C 0.5807(9) 0.0293(3) 0.9986(8) 0.046(2) Uani 1 1 d . . . . .
H12B H 0.563293 0.008576 1.065813 0.056 Uiso 1 1 calc R U . . .
C13B C 0.7018(8) 0.0531(3) 0.9943(6) 0.0389(16) Uani 1 1 d . . . . .
H13B H 0.767593 0.048941 1.059082 0.047 Uiso 1 1 calc R U . . .
C14B C 0.7267(6) 0.0831(3) 0.8948(6) 0.0310(13) Uani 1 1 d . . . . .
H14B H 0.810436 0.098683 0.891417 0.037 Uiso 1 1 calc R U . . .
C15B C 0.6765(7) 0.4175(3) 0.8661(6) 0.0282(14) Uani 1 1 d . . . . .
S1C S 0.24231(14) 0.75976(6) 0.97460(12) 0.0212(4) Uani 1 1 d . . . . .
F1C F -0.0245(4) 0.5743(2) 0.6378(5) 0.0518(13) Uani 1 1 d . . . . .
F2C F 0.1631(5) 0.54276(19) 0.6826(4) 0.0419(11) Uani 1 1 d . . . . .
F3C F 0.1348(5) 0.5921(2) 0.5302(4) 0.0443(12) Uani 1 1 d . . . . .
O1C O 0.2085(4) 0.7463(2) 1.0927(3) 0.0273(10) Uani 1 1 d . . . . .
O2C O 0.3729(4) 0.7751(2) 0.9547(4) 0.0261(10) Uani 1 1 d . . . . .
N1C N 0.1447(5) 0.8063(2) 0.9281(5) 0.0232(11) Uani 1 1 d D . . . .
H1NC H 0.065(3) 0.798(2) 0.948(5) 0.015(15) Uiso 1 1 d D . . . .
C1C C 0.1332(6) 0.6288(3) 0.7216(6) 0.0227(13) Uani 1 1 d . . . . .
C2C C 0.2342(5) 0.6623(3) 0.6981(5) 0.0198(12) Uani 1 1 d . . . . .
H2C H 0.280344 0.657418 0.627485 0.024 Uiso 1 1 calc R U . . .
C3C C 0.2692(6) 0.7024(3) 0.7747(5) 0.0225(13) Uani 1 1 d . . . . .
H3C H 0.336617 0.725270 0.755795 0.027 Uiso 1 1 calc R U . . .
C4C C 0.2047(5) 0.7085(3) 0.8784(5) 0.0173(12) Uani 1 1 d . . . . .
C5C C 0.1053(6) 0.6756(3) 0.9070(6) 0.0237(13) Uani 1 1 d . . . . .
H5C H 0.059268 0.680387 0.977730 0.028 Uiso 1 1 calc R U . . .
C6C C 0.0757(5) 0.6356(3) 0.8286(5) 0.0189(12) Uani 1 1 d . . . . .
H6C H 0.012129 0.611550 0.850122 0.023 Uiso 1 1 calc R U . . .
C7C C 0.1684(7) 0.8322(3) 0.8121(5) 0.0254(13) Uani 1 1 d . . . . .
H8E H 0.142758 0.809641 0.742768 0.030 Uiso 1 1 calc R U . . .
H8F H 0.262981 0.840446 0.810105 0.030 Uiso 1 1 calc R U . . .
C8C C 0.0859(8) 0.8811(3) 0.8030(6) 0.0324(15) Uani 1 1 d . . . . .
H9E H -0.008688 0.872160 0.795385 0.039 Uiso 1 1 calc R U . . .
H9F H 0.103175 0.901070 0.878284 0.039 Uiso 1 1 calc R U . . .
C9C C 0.1172(7) 0.9128(3) 0.6964(6) 0.0265(14) Uani 1 1 d . . . . .
C10C C 0.2386(6) 0.9364(2) 0.6892(6) 0.0298(12) Uani 1 1 d . . . . .
H10C H 0.304942 0.932187 0.753526 0.036 Uiso 1 1 calc R U . . .
C11C C 0.2648(6) 0.9662(3) 0.5898(6) 0.0377(15) Uani 1 1 d . . . . .
H11C H 0.348107 0.982076 0.586225 0.045 Uiso 1 1 calc R U . . .
C12C C 0.1679(7) 0.9723(3) 0.4962(6) 0.0294(14) Uani 1 1 d . . . . .
H12C H 0.184164 0.992725 0.428280 0.035 Uiso 1 1 calc R U . . .
C13C C 0.0475(6) 0.9486(3) 0.5016(5) 0.0330(14) Uani 1 1 d . . . . .
H13C H -0.018880 0.952953 0.437457 0.040 Uiso 1 1 calc R U . . .
C14C C 0.0232(6) 0.9185(3) 0.5999(5) 0.0292(12) Uani 1 1 d . . . . .
H14C H -0.058899 0.901450 0.601340 0.035 Uiso 1 1 calc R U . . .
C15C C 0.0996(6) 0.5851(3) 0.6452(5) 0.0259(14) Uani 1 1 d . . . . .
S1D S 0.74518(14) 0.75355(5) 0.98590(12) 0.0201(3) Uani 1 1 d . . . . .
F1D F 0.4521(6) 0.5761(3) 0.6376(6) 0.081(2) Uani 1 1 d . . . . .
F2D F 0.6370(7) 0.5427(2) 0.6756(5) 0.0645(17) Uani 1 1 d . . . . .
F3D F 0.6086(6) 0.5935(2) 0.5295(4) 0.0589(16) Uani 1 1 d . . . . .
O1D O 0.7136(5) 0.7380(2) 1.1032(4) 0.0280(11) Uani 1 1 d . . . . .
O2D O 0.8764(4) 0.7670(2) 0.9632(4) 0.0260(10) Uani 1 1 d . . . . .
N1D N 0.6537(6) 0.8025(2) 0.9498(5) 0.0252(12) Uani 1 1 d D . . . .
H1ND H 0.572(3) 0.796(2) 0.963(5) 0.001(11) Uiso 1 1 d D . . . .
C1D C 0.6156(6) 0.6279(3) 0.7238(6) 0.0217(13) Uani 1 1 d . . . . .
C2D C 0.7238(5) 0.6586(3) 0.7028(5) 0.0200(12) Uani 1 1 d . . . . .
H2D H 0.770780 0.652806 0.633192 0.024 Uiso 1 1 calc R U . . .
C3D C 0.7631(6) 0.6972(3) 0.7820(5) 0.0226(13) Uani 1 1 d . . . . .
H3D H 0.834817 0.718468 0.765290 0.027 Uiso 1 1 calc R U . . .
C4D C 0.6985(5) 0.7048(3) 0.8848(5) 0.0190(12) Uani 1 1 d . . . . .
C5D C 0.5916(7) 0.6743(3) 0.9101(6) 0.0245(14) Uani 1 1 d . . . . .
H5D H 0.544636 0.680259 0.979675 0.029 Uiso 1 1 calc R U . . .
C6D C 0.5565(7) 0.6355(3) 0.8311(6) 0.0272(14) Uani 1 1 d . . . . .
H6D H 0.488829 0.612860 0.850949 0.033 Uiso 1 1 calc R U . . .
C7D C 0.6752(7) 0.8298(3) 0.8347(6) 0.0255(13) Uani 1 1 d . . . . .
H8G H 0.650940 0.807797 0.764085 0.031 Uiso 1 1 calc R U . . .
H8H H 0.768966 0.839394 0.832852 0.031 Uiso 1 1 calc R U . . .
C8D C 0.5879(8) 0.8778(3) 0.8299(6) 0.0350(17) Uani 1 1 d . . . . .
H9G H 0.494020 0.867820 0.824863 0.042 Uiso 1 1 calc R U . . .
H9H H 0.606503 0.897865 0.904851 0.042 Uiso 1 1 calc R U . . .
C9D C 0.6150(6) 0.9096(3) 0.7208(5) 0.0214(13) Uani 1 1 d . . . . .
C10D C 0.6908(6) 0.9535(2) 0.7305(5) 0.0271(11) Uani 1 1 d . . . . .
H10D H 0.728247 0.964084 0.807600 0.032 Uiso 1 1 calc R U . . .
C11D C 0.7121(6) 0.9822(3) 0.6268(6) 0.0329(13) Uani 1 1 d . . . . .
H11D H 0.764501 1.011999 0.634407 0.039 Uiso 1 1 calc R U . . .
C12D C 0.6579(6) 0.9677(3) 0.5143(6) 0.0248(13) Uani 1 1 d . . . . .
H12D H 0.672545 0.987104 0.444302 0.030 Uiso 1 1 calc R U . . .
C13D C 0.5807(6) 0.9237(3) 0.5049(5) 0.0304(13) Uani 1 1 d . . . . .
H13D H 0.541897 0.913504 0.427916 0.036 Uiso 1 1 calc R U . . .
C14D C 0.5605(6) 0.8951(3) 0.6056(5) 0.0247(12) Uani 1 1 d . . . . .
H14D H 0.508847 0.865186 0.597234 0.030 Uiso 1 1 calc R U . . .
C15D C 0.5781(7) 0.5856(3) 0.6453(6) 0.0314(15) 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
S1A O2A 1.439(4) . ?
S1A O1A 1.447(5) . ?
S1A N1A 1.612(6) . ?
S1A C4A 1.792(7) . ?
F1A C15A 1.321(7) . ?
F2A C15A 1.350(9) . ?
F3A C15A 1.363(8) . ?
N1A C7A 1.463(8) . ?
N1A H1NA 0.88(3) . ?
C1A C2A 1.364(10) . ?
C1A C6A 1.420(8) . ?
C1A C15A 1.549(9) . ?
C2A C3A 1.393(9) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.407(7) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.392(9) . ?
C5A C6A 1.384(10) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
C7A C8A 1.506(9) . ?
C7A H7A 0.9900 . ?
C7A H8B 0.9900 . ?
C8A C9A 1.506(8) . ?
C8A H8A 0.9900 . ?
C8A H9B 0.9900 . ?
C9A C10A 1.362(8) . ?
C9A C14A 1.391(9) . ?
C10A C11A 1.408(9) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.379(11) . ?
C11A H11A 0.9500 . ?
C12A C13A 1.375(11) . ?
C12A H12A 0.9500 . ?
C13A C14A 1.381(8) . ?
C13A H13A 0.9500 . ?
C14A H14A 0.9500 . ?
S1B O2B 1.440(4) . ?
S1B O1B 1.445(5) . ?
S1B N1B 1.606(6) . ?
S1B C4B 1.792(6) . ?
F1B C15B 1.312(8) . ?
F2B C15B 1.347(9) . ?
F3B C15B 1.337(8) . ?
N1B C7B 1.466(8) . ?
N1B H1NB 0.89(3) . ?
C1B C2B 1.370(10) . ?
C1B C6B 1.402(8) . ?
C1B C15B 1.542(9) . ?
C2B C3B 1.403(9) . ?
C2B H17 0.9500 . ?
C3B C4B 1.409(7) . ?
C3B H18 0.9500 . ?
C4B C5B 1.384(8) . ?
C5B C6B 1.398(9) . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
C7B C8B 1.515(10) . ?
C7B H8C 0.9900 . ?
C7B H8D 0.9900 . ?
C8B C9B 1.529(9) . ?
C8B H9C 0.9900 . ?
C8B H9D 0.9900 . ?
C9B C14B 1.375(9) . ?
C9B C10B 1.387(9) . ?
C10B C11B 1.380(9) . ?
C10B H10B 0.9500 . ?
C11B C12B 1.378(12) . ?
C11B H11B 0.9500 . ?
C12B C13B 1.389(12) . ?
C12B H12B 0.9500 . ?
C13B C14B 1.395(9) . ?
C13B H13B 0.9500 . ?
C14B H14B 0.9500 . ?
S1C O1C 1.421(4) . ?
S1C O2C 1.424(5) . ?
S1C N1C 1.639(6) . ?
S1C C4C 1.745(7) . ?
F1C C15C 1.293(8) . ?
F2C C15C 1.340(9) . ?
F3C C15C 1.360(7) . ?
N1C C7C 1.489(8) . ?
N1C H1NC 0.88(3) . ?
C1C C6C 1.372(9) . ?
C1C C2C 1.396(9) . ?
C1C C15C 1.454(10) . ?
C2C C3C 1.385(9) . ?
C2C H2C 0.9500 . ?
C3C C4C 1.374(8) . ?
C3C H3C 0.9500 . ?
C4C C5C 1.389(9) . ?
C5C C6C 1.385(9) . ?
C5C H5C 0.9500 . ?
C6C H6C 0.9500 . ?
C7C C8C 1.539(10) . ?
C7C H8E 0.9900 . ?
C7C H8F 0.9900 . ?
C8C C9C 1.499(9) . ?
C8C H9E 0.9900 . ?
C8C H9F 0.9900 . ?
C9C C14C 1.388(9) . ?
C9C C10C 1.393(9) . ?
C10C C11C 1.393(9) . ?
C10C H10C 0.9500 . ?
C11C C12C 1.385(10) . ?
C11C H11C 0.9500 . ?
C12C C13C 1.382(10) . ?
C12C H12C 0.9500 . ?
C13C C14C 1.384(8) . ?
C13C H13C 0.9500 . ?
C14C H14C 0.9500 . ?
S1D O1D 1.421(4) . ?
S1D O2D 1.424(5) . ?
S1D N1D 1.624(6) . ?
S1D C4D 1.748(7) . ?
F1D C15D 1.304(9) . ?
F2D C15D 1.311(10) . ?
F3D C15D 1.357(8) . ?
N1D C7D 1.494(8) . ?
N1D H1ND 0.88(3) . ?
C1D C6D 1.385(9) . ?
C1D C2D 1.401(9) . ?
C1D C15D 1.448(10) . ?
C2D C3D 1.383(10) . ?
C2D H2D 0.9500 . ?
C3D C4D 1.371(8) . ?
C3D H3D 0.9500 . ?
C4D C5D 1.398(9) . ?
C5D C6D 1.376(10) . ?
C5D H5D 0.9500 . ?
C6D H6D 0.9500 . ?
C7D C8D 1.544(10) . ?
C7D H8G 0.9900 . ?
C7D H8H 0.9900 . ?
C8D C9D 1.512(9) . ?
C8D H9G 0.9900 . ?
C8D H9H 0.9900 . ?
C9D C10D 1.391(9) . ?
C9D C14D 1.404(8) . ?
C10D C11D 1.405(8) . ?
C10D H10D 0.9500 . ?
C11D C12D 1.378(9) . ?
C11D H11D 0.9500 . ?
C12D C13D 1.400(10) . ?
C12D H12D 0.9500 . ?
C13D C14D 1.373(8) . ?
C13D H13D 0.9500 . ?
C14D H14D 0.9500 . ?

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
O2A S1A O1A 119.5(3) . . ?
O2A S1A N1A 107.3(3) . . ?
O1A S1A N1A 107.5(3) . . ?
O2A S1A C4A 107.2(3) . . ?
O1A S1A C4A 107.9(3) . . ?
N1A S1A C4A 106.8(3) . . ?
C7A N1A S1A 119.5(4) . . ?
C7A N1A H1NA 110(5) . . ?
S1A N1A H1NA 108(6) . . ?
C2A C1A C6A 124.6(6) . . ?
C2A C1A C15A 119.2(5) . . ?
C6A C1A C15A 116.2(6) . . ?
C1A C2A C3A 118.3(5) . . ?
C1A C2A H2A 120.9 . . ?
C3A C2A H2A 120.9 . . ?
C2A C3A C4A 118.4(6) . . ?
C2A C3A H3A 120.8 . . ?
C4A C3A H3A 120.8 . . ?
C5A C4A C3A 122.2(6) . . ?
C5A C4A S1A 119.9(4) . . ?
C3A C4A S1A 117.9(5) . . ?
C6A C5A C4A 119.9(5) . . ?
C6A C5A H5A 120.0 . . ?
C4A C5A H5A 120.0 . . ?
C5A C6A C1A 116.2(6) . . ?
C5A C6A H6A 121.9 . . ?
C1A C6A H6A 121.9 . . ?
N1A C7A C8A 110.3(5) . . ?
N1A C7A H7A 109.6 . . ?
C8A C7A H7A 109.6 . . ?
N1A C7A H8B 109.6 . . ?
C8A C7A H8B 109.6 . . ?
H7A C7A H8B 108.1 . . ?
C9A C8A C7A 112.8(5) . . ?
C9A C8A H8A 109.0 . . ?
C7A C8A H8A 109.0 . . ?
C9A C8A H9B 109.0 . . ?
C7A C8A H9B 109.0 . . ?
H8A C8A H9B 107.8 . . ?
C10A C9A C14A 119.3(6) . . ?
C10A C9A C8A 120.7(6) . . ?
C14A C9A C8A 119.9(5) . . ?
C9A C10A C11A 120.9(6) . . ?
C9A C10A H10A 119.5 . . ?
C11A C10A H10A 119.5 . . ?
C12A C11A C10A 119.1(6) . . ?
C12A C11A H11A 120.5 . . ?
C10A C11A H11A 120.5 . . ?
C13A C12A C11A 120.0(7) . . ?
C13A C12A H12A 120.0 . . ?
C11A C12A H12A 120.0 . . ?
C12A C13A C14A 120.6(6) . . ?
C12A C13A H13A 119.7 . . ?
C14A C13A H13A 119.7 . . ?
C13A C14A C9A 120.1(6) . . ?
C13A C14A H14A 120.0 . . ?
C9A C14A H14A 120.0 . . ?
F1A C15A F2A 107.6(6) . . ?
F1A C15A F3A 107.3(5) . . ?
F2A C15A F3A 107.1(6) . . ?
F1A C15A C1A 113.1(6) . . ?
F2A C15A C1A 109.5(5) . . ?
F3A C15A C1A 111.9(5) . . ?
O2B S1B O1B 119.5(3) . . ?
O2B S1B N1B 107.4(3) . . ?
O1B S1B N1B 107.4(3) . . ?
O2B S1B C4B 107.1(3) . . ?
O1B S1B C4B 108.3(3) . . ?
N1B S1B C4B 106.4(3) . . ?
C7B N1B S1B 120.2(4) . . ?
C7B N1B H1NB 101(5) . . ?
S1B N1B H1NB 115(5) . . ?
C2B C1B C6B 124.3(6) . . ?
C2B C1B C15B 118.2(5) . . ?
C6B C1B C15B 117.5(6) . . ?
C1B C2B C3B 118.9(6) . . ?
C1B C2B H17 120.6 . . ?
C3B C2B H17 120.6 . . ?
C2B C3B C4B 117.4(6) . . ?
C2B C3B H18 121.3 . . ?
C4B C3B H18 121.3 . . ?
C5B C4B C3B 122.9(6) . . ?
C5B C4B S1B 119.3(4) . . ?
C3B C4B S1B 117.8(5) . . ?
C4B C5B C6B 119.5(5) . . ?
C4B C5B H5B 120.2 . . ?
C6B C5B H5B 120.2 . . ?
C5B C6B C1B 116.8(6) . . ?
C5B C6B H6B 121.6 . . ?
C1B C6B H6B 121.6 . . ?
N1B C7B C8B 109.5(5) . . ?
N1B C7B H8C 109.8 . . ?
C8B C7B H8C 109.8 . . ?
N1B C7B H8D 109.8 . . ?
C8B C7B H8D 109.8 . . ?
H8C C7B H8D 108.2 . . ?
C7B C8B C9B 112.4(5) . . ?
C7B C8B H9C 109.1 . . ?
C9B C8B H9C 109.1 . . ?
C7B C8B H9D 109.1 . . ?
C9B C8B H9D 109.1 . . ?
H9C C8B H9D 107.9 . . ?
C14B C9B C10B 118.3(6) . . ?
C14B C9B C8B 122.6(6) . . ?
C10B C9B C8B 119.0(6) . . ?
C11B C10B C9B 121.4(6) . . ?
C11B C10B H10B 119.3 . . ?
C9B C10B H10B 119.3 . . ?
C12B C11B C10B 120.1(7) . . ?
C12B C11B H11B 119.9 . . ?
C10B C11B H11B 119.9 . . ?
C11B C12B C13B 119.3(7) . . ?
C11B C12B H12B 120.3 . . ?
C13B C12B H12B 120.3 . . ?
C12B C13B C14B 119.9(7) . . ?
C12B C13B H13B 120.0 . . ?
C14B C13B H13B 120.0 . . ?
C9B C14B C13B 120.9(6) . . ?
C9B C14B H14B 119.6 . . ?
C13B C14B H14B 119.6 . . ?
F1B C15B F3B 107.7(5) . . ?
F1B C15B F2B 106.4(6) . . ?
F3B C15B F2B 107.3(6) . . ?
F1B C15B C1B 113.7(6) . . ?
F3B C15B C1B 112.5(6) . . ?
F2B C15B C1B 108.9(5) . . ?
O1C S1C O2C 120.5(3) . . ?
O1C S1C N1C 107.0(3) . . ?
O2C S1C N1C 106.9(3) . . ?
O1C S1C C4C 108.1(3) . . ?
O2C S1C C4C 106.9(3) . . ?
N1C S1C C4C 106.8(3) . . ?
C7C N1C S1C 118.7(4) . . ?
C7C N1C H1NC 122(4) . . ?
S1C N1C H1NC 107(4) . . ?
C6C C1C C2C 116.5(6) . . ?
C6C C1C C15C 120.6(6) . . ?
C2C C1C C15C 122.5(6) . . ?
C3C C2C C1C 121.9(6) . . ?
C3C C2C H2C 119.0 . . ?
C1C C2C H2C 119.0 . . ?
C4C C3C C2C 119.0(6) . . ?
C4C C3C H3C 120.5 . . ?
C2C C3C H3C 120.5 . . ?
C3C C4C C5C 121.3(6) . . ?
C3C C4C S1C 120.3(5) . . ?
C5C C4C S1C 118.4(5) . . ?
C6C C5C C4C 117.5(5) . . ?
C6C C5C H5C 121.3 . . ?
C4C C5C H5C 121.3 . . ?
C1C C6C C5C 123.7(6) . . ?
C1C C6C H6C 118.2 . . ?
C5C C6C H6C 118.2 . . ?
N1C C7C C8C 108.5(5) . . ?
N1C C7C H8E 110.0 . . ?
C8C C7C H8E 110.0 . . ?
N1C C7C H8F 110.0 . . ?
C8C C7C H8F 110.0 . . ?
H8E C7C H8F 108.4 . . ?
C9C C8C C7C 111.8(6) . . ?
C9C C8C H9E 109.2 . . ?
C7C C8C H9E 109.2 . . ?
C9C C8C H9F 109.2 . . ?
C7C C8C H9F 109.2 . . ?
H9E C8C H9F 107.9 . . ?
C14C C9C C10C 118.2(6) . . ?
C14C C9C C8C 119.3(6) . . ?
C10C C9C C8C 122.5(6) . . ?
C9C C10C C11C 121.4(6) . . ?
C9C C10C H10C 119.3 . . ?
C11C C10C H10C 119.3 . . ?
C12C C11C C10C 119.1(6) . . ?
C12C C11C H11C 120.4 . . ?
C10C C11C H11C 120.4 . . ?
C13C C12C C11C 120.0(6) . . ?
C13C C12C H12C 120.0 . . ?
C11C C12C H12C 120.0 . . ?
C12C C13C C14C 120.4(6) . . ?
C12C C13C H13C 119.8 . . ?
C14C C13C H13C 119.8 . . ?
C13C C14C C9C 120.7(6) . . ?
C13C C14C H14C 119.6 . . ?
C9C C14C H14C 119.6 . . ?
F1C C15C F2C 106.5(7) . . ?
F1C C15C F3C 107.2(5) . . ?
F2C C15C F3C 104.3(6) . . ?
F1C C15C C1C 113.4(6) . . ?
F2C C15C C1C 113.2(5) . . ?
F3C C15C C1C 111.7(6) . . ?
O1D S1D O2D 120.9(3) . . ?
O1D S1D N1D 106.8(3) . . ?
O2D S1D N1D 106.8(3) . . ?
O1D S1D C4D 107.6(3) . . ?
O2D S1D C4D 106.5(3) . . ?
N1D S1D C4D 107.7(3) . . ?
C7D N1D S1D 118.4(4) . . ?
C7D N1D H1ND 116(4) . . ?
S1D N1D H1ND 109(4) . . ?
C6D C1D C2D 117.2(6) . . ?
C6D C1D C15D 120.8(6) . . ?
C2D C1D C15D 121.4(6) . . ?
C3D C2D C1D 121.0(5) . . ?
C3D C2D H2D 119.5 . . ?
C1D C2D H2D 119.5 . . ?
C4D C3D C2D 119.8(6) . . ?
C4D C3D H3D 120.1 . . ?
C2D C3D H3D 120.1 . . ?
C3D C4D C5D 120.9(7) . . ?
C3D C4D S1D 120.8(5) . . ?
C5D C4D S1D 118.3(5) . . ?
C6D C5D C4D 118.0(6) . . ?
C6D C5D H5D 121.0 . . ?
C4D C5D H5D 121.0 . . ?
C5D C6D C1D 122.8(7) . . ?
C5D C6D H6D 118.6 . . ?
C1D C6D H6D 118.6 . . ?
N1D C7D C8D 107.7(5) . . ?
N1D C7D H8G 110.2 . . ?
C8D C7D H8G 110.2 . . ?
N1D C7D H8H 110.2 . . ?
C8D C7D H8H 110.2 . . ?
H8G C7D H8H 108.5 . . ?
C9D C8D C7D 110.0(5) . . ?
C9D C8D H9G 109.7 . . ?
C7D C8D H9G 109.7 . . ?
C9D C8D H9H 109.7 . . ?
C7D C8D H9H 109.7 . . ?
H9G C8D H9H 108.2 . . ?
C10D C9D C14D 118.4(6) . . ?
C10D C9D C8D 122.3(6) . . ?
C14D C9D C8D 119.3(6) . . ?
C9D C10D C11D 120.4(5) . . ?
C9D C10D H10D 119.8 . . ?
C11D C10D H10D 119.8 . . ?
C12D C11D C10D 120.7(6) . . ?
C12D C11D H11D 119.6 . . ?
C10D C11D H11D 119.6 . . ?
C11D C12D C13D 118.9(6) . . ?
C11D C12D H12D 120.6 . . ?
C13D C12D H12D 120.6 . . ?
C14D C13D C12D 120.8(5) . . ?
C14D C13D H13D 119.6 . . ?
C12D C13D H13D 119.6 . . ?
C13D C14D C9D 120.9(6) . . ?
C13D C14D H14D 119.5 . . ?
C9D C14D H14D 119.5 . . ?
F1D C15D F2D 106.3(7) . . ?
F1D C15D F3D 105.3(6) . . ?
F2D C15D F3D 103.9(6) . . ?
F1D C15D C1D 113.6(6) . . ?
F2D C15D C1D 114.6(6) . . ?
F3D C15D C1D 112.3(7) . . ?

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
O2A S1A N1A C7A -175.3(5) . . . . ?
O1A S1A N1A C7A -45.6(5) . . . . ?
C4A S1A N1A C7A 70.0(5) . . . . ?
C6A C1A C2A C3A -5.4(11) . . . . ?
C15A C1A C2A C3A 177.9(6) . . . . ?
C1A C2A C3A C4A 1.4(10) . . . . ?
C2A C3A C4A C5A 0.7(10) . . . . ?
C2A C3A C4A S1A 179.3(5) . . . . ?
O2A S1A C4A C5A -26.7(6) . . . . ?
O1A S1A C4A C5A -156.7(5) . . . . ?
N1A S1A C4A C5A 88.1(6) . . . . ?
O2A S1A C4A C3A 154.6(5) . . . . ?
O1A S1A C4A C3A 24.7(6) . . . . ?
N1A S1A C4A C3A -90.6(6) . . . . ?
C3A C4A C5A C6A 1.1(10) . . . . ?
S1A C4A C5A C6A -177.5(5) . . . . ?
C4A C5A C6A C1A -4.6(10) . . . . ?
C2A C1A C6A C5A 7.0(11) . . . . ?
C15A C1A C6A C5A -176.2(6) . . . . ?
S1A N1A C7A C8A 168.3(4) . . . . ?
N1A C7A C8A C9A -177.5(5) . . . . ?
C7A C8A C9A C10A -72.4(7) . . . . ?
C7A C8A C9A C14A 105.9(7) . . . . ?
C14A C9A C10A C11A 1.6(9) . . . . ?
C8A C9A C10A C11A 179.9(5) . . . . ?
C9A C10A C11A C12A -1.4(9) . . . . ?
C10A C11A C12A C13A 0.2(10) . . . . ?
C11A C12A C13A C14A 0.9(11) . . . . ?
C12A C13A C14A C9A -0.7(10) . . . . ?
C10A C9A C14A C13A -0.5(9) . . . . ?
C8A C9A C14A C13A -178.8(6) . . . . ?
C2A C1A C15A F1A 22.9(9) . . . . ?
C6A C1A C15A F1A -154.1(6) . . . . ?
C2A C1A C15A F2A -97.2(7) . . . . ?
C6A C1A C15A F2A 85.8(7) . . . . ?
C2A C1A C15A F3A 144.2(6) . . . . ?
C6A C1A C15A F3A -32.8(8) . . . . ?
O2B S1B N1B C7B -174.6(5) . . . . ?
O1B S1B N1B C7B -44.8(5) . . . . ?
C4B S1B N1B C7B 71.0(5) . . . . ?
C6B C1B C2B C3B -4.4(10) . . . . ?
C15B C1B C2B C3B 179.6(6) . . . . ?
C1B C2B C3B C4B 1.9(9) . . . . ?
C2B C3B C4B C5B -1.3(9) . . . . ?
C2B C3B C4B S1B 177.3(5) . . . . ?
O2B S1B C4B C5B -30.9(6) . . . . ?
O1B S1B C4B C5B -161.0(5) . . . . ?
N1B S1B C4B C5B 83.8(5) . . . . ?
O2B S1B C4B C3B 150.5(5) . . . . ?
O1B S1B C4B C3B 20.3(6) . . . . ?
N1B S1B C4B C3B -94.9(5) . . . . ?
C3B C4B C5B C6B 2.8(9) . . . . ?
S1B C4B C5B C6B -175.7(5) . . . . ?
C4B C5B C6B C1B -4.8(9) . . . . ?
C2B C1B C6B C5B 5.8(10) . . . . ?
C15B C1B C6B C5B -178.1(6) . . . . ?
S1B N1B C7B C8B 163.2(4) . . . . ?
N1B C7B C8B C9B -174.0(5) . . . . ?
C7B C8B C9B C14B -107.2(7) . . . . ?
C7B C8B C9B C10B 76.8(8) . . . . ?
C14B C9B C10B C11B 1.4(10) . . . . ?
C8B C9B C10B C11B 177.5(6) . . . . ?
C9B C10B C11B C12B -0.3(10) . . . . ?
C10B C11B C12B C13B -0.2(11) . . . . ?
C11B C12B C13B C14B -0.4(11) . . . . ?
C10B C9B C14B C13B -2.0(10) . . . . ?
C8B C9B C14B C13B -178.0(6) . . . . ?
C12B C13B C14B C9B 1.5(10) . . . . ?
C2B C1B C15B F1B 22.1(9) . . . . ?
C6B C1B C15B F1B -154.2(6) . . . . ?
C2B C1B C15B F3B 144.8(7) . . . . ?
C6B C1B C15B F3B -31.5(9) . . . . ?
C2B C1B C15B F2B -96.3(8) . . . . ?
C6B C1B C15B F2B 87.4(8) . . . . ?
O1C S1C N1C C7C 173.0(5) . . . . ?
O2C S1C N1C C7C 42.7(6) . . . . ?
C4C S1C N1C C7C -71.5(6) . . . . ?
C6C C1C C2C C3C -4.1(9) . . . . ?
C15C C1C C2C C3C -177.0(6) . . . . ?
C1C C2C C3C C4C 1.7(10) . . . . ?
C2C C3C C4C C5C -0.4(10) . . . . ?
C2C C3C C4C S1C -177.9(5) . . . . ?
O1C S1C C4C C3C -155.3(5) . . . . ?
O2C S1C C4C C3C -24.2(6) . . . . ?
N1C S1C C4C C3C 89.9(5) . . . . ?
O1C S1C C4C C5C 27.1(6) . . . . ?
O2C S1C C4C C5C 158.2(5) . . . . ?
N1C S1C C4C C5C -87.7(6) . . . . ?
C3C C4C C5C C6C 1.6(10) . . . . ?
S1C C4C C5C C6C 179.1(5) . . . . ?
C2C C1C C6C C5C 5.4(9) . . . . ?
C15C C1C C6C C5C 178.4(6) . . . . ?
C4C C5C C6C C1C -4.2(10) . . . . ?
S1C N1C C7C C8C -167.5(5) . . . . ?
N1C C7C C8C C9C 172.7(6) . . . . ?
C7C C8C C9C C14C 111.8(7) . . . . ?
C7C C8C C9C C10C -67.1(9) . . . . ?
C14C C9C C10C C11C 1.7(10) . . . . ?
C8C C9C C10C C11C -179.3(6) . . . . ?
C9C C10C C11C C12C -0.1(10) . . . . ?
C10C C11C C12C C13C -0.7(10) . . . . ?
C11C C12C C13C C14C -0.3(11) . . . . ?
C12C C13C C14C C9C 2.1(10) . . . . ?
C10C C9C C14C C13C -2.8(10) . . . . ?
C8C C9C C14C C13C 178.3(6) . . . . ?
C6C C1C C15C F1C 40.9(9) . . . . ?
C2C C1C C15C F1C -146.5(6) . . . . ?
C6C C1C C15C F2C -80.6(8) . . . . ?
C2C C1C C15C F2C 92.1(8) . . . . ?
C6C C1C C15C F3C 162.1(6) . . . . ?
C2C C1C C15C F3C -25.3(9) . . . . ?
O1D S1D N1D C7D 174.5(5) . . . . ?
O2D S1D N1D C7D 43.8(6) . . . . ?
C4D S1D N1D C7D -70.2(6) . . . . ?
C6D C1D C2D C3D -4.7(9) . . . . ?
C15D C1D C2D C3D -176.4(6) . . . . ?
C1D C2D C3D C4D 2.1(10) . . . . ?
C2D C3D C4D C5D -0.9(10) . . . . ?
C2D C3D C4D S1D -179.5(5) . . . . ?
O1D S1D C4D C3D -151.1(5) . . . . ?
O2D S1D C4D C3D -20.2(6) . . . . ?
N1D S1D C4D C3D 94.1(6) . . . . ?
O1D S1D C4D C5D 30.2(6) . . . . ?
O2D S1D C4D C5D 161.2(5) . . . . ?
N1D S1D C4D C5D -84.5(6) . . . . ?
C3D C4D C5D C6D 2.3(10) . . . . ?
S1D C4D C5D C6D -179.1(5) . . . . ?
C4D C5D C6D C1D -5.2(10) . . . . ?
C2D C1D C6D C5D 6.3(10) . . . . ?
C15D C1D C6D C5D 178.1(6) . . . . ?
S1D N1D C7D C8D -173.5(5) . . . . ?
N1D C7D C8D C9D 174.8(6) . . . . ?
C7D C8D C9D C10D -103.2(7) . . . . ?
C7D C8D C9D C14D 77.9(8) . . . . ?
C14D C9D C10D C11D -0.4(9) . . . . ?
C8D C9D C10D C11D -179.2(6) . . . . ?
C9D C10D C11D C12D 0.4(9) . . . . ?
C10D C11D C12D C13D 0.1(9) . . . . ?
C11D C12D C13D C14D -0.8(10) . . . . ?
C12D C13D C14D C9D 0.9(10) . . . . ?
C10D C9D C14D C13D -0.3(9) . . . . ?
C8D C9D C14D C13D 178.6(6) . . . . ?
C6D C1D C15D F1D 39.0(10) . . . . ?
C2D C1D C15D F1D -149.6(7) . . . . ?
C6D C1D C15D F2D -83.5(8) . . . . ?
C2D C1D C15D F2D 88.0(8) . . . . ?
C6D C1D C15D F3D 158.3(6) . . . . ?
C2D C1D C15D F3D -30.3(9) . . . . ?

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
_geom_hbond_publ_flag
N1A H1NA O1B 0.88(3) 2.06(3) 2.942(7) 179(9) . yes
C3A H3A O1C 0.95 2.48 3.257(7) 138.5 2_547 yes
C3B H18 O1D 0.95 2.50 3.354(8) 148.9 2_647 yes
N1B H1NB O1A 0.89(3) 2.13(4) 2.969(7) 158(7) 1_655 yes
N1C H1NC O2D 0.88(3) 2.11(3) 2.977(7) 168(6) 1_455 yes
C3C H3C O2B 0.95 2.46 3.278(8) 144.3 2_656 yes
C7C H8E O2A 0.99 2.64 3.531(8) 149.5 2_556 yes
C3D H3D O2A 0.95 2.51 3.342(8) 146.9 2_656 yes
N1D H1ND O2C 0.88(3) 2.09(3) 2.956(7) 168(5) . yes

_refine_diff_density_max         0.662
_refine_diff_density_min         -0.758
_refine_diff_density_rms         0.078

####################################################################### 
# 
# 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_5b
_database_code_depnum_ccdc_archive 'CCDC 2337445'
loop_
_audit_author_name
_audit_author_address
'Rajesh Gonnade'
;CSIR NATIONAL CHEMICAL LABORATORY PUNE INDIA
India
;
_audit_update_record             
;
2024-03-02 deposited with the CCDC.	2024-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H15 N O2 S'
_chemical_formula_sum            'C14 H15 N O2 S'
_chemical_formula_weight         261.33

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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

_cell_length_a                   9.1017(4)
_cell_length_b                   5.7077(2)
_cell_length_c                   25.1568(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1306.89(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9558
_cell_measurement_theta_min      4.05
_cell_measurement_theta_max      36.87

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_F_000             552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.241
_shelx_estimated_absorpt_T_min   0.936
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.6749
_exptl_absorpt_correction_T_max  0.7473
_exptl_absorpt_process_details   'SADABS,(Bruker, 2006)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_source_type              'Incoatech I\mS HB'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            15214
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         4.516
_diffrn_reflns_theta_max         26.980
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             2829
_reflns_number_gt                2802
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.954
_reflns_Friedel_fraction_max     0.990
_reflns_Friedel_fraction_full    0.988

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

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0281P)²+0.5027P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'direct method'
_atom_sites_solution_secondary   'difference Fourier'
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1341 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.012(14)
_chemical_absolute_configuration .
_refine_ls_number_reflns         2829
_refine_ls_number_parameters     167
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0244
_refine_ls_R_factor_gt           0.0241
_refine_ls_wR_factor_ref         0.0626
_refine_ls_wR_factor_gt          0.0624
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.082
_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
S1 S 0.49169(4) 0.44289(7) 0.54283(3) 0.01306(11) Uani 1 1 d . . . . .
O1 O 0.47363(14) 0.6924(2) 0.54517(7) 0.0185(3) Uani 1 1 d . . . . .
O2 O 0.36660(14) 0.2992(2) 0.52983(6) 0.0169(3) Uani 1 1 d . . . . .
N1 N 0.61699(18) 0.3919(3) 0.49885(7) 0.0142(3) Uani 1 1 d . . . . .
C1 C 0.6731(3) 0.2051(4) 0.70162(9) 0.0259(5) Uani 1 1 d . . . . .
H1 H 0.7127 0.1551 0.7347 0.031 Uiso 1 1 calc R U . . .
C2 C 0.7201(3) 0.4145(4) 0.67903(9) 0.0245(5) Uani 1 1 d . . . . .
H2 H 0.7918 0.5071 0.6967 0.029 Uiso 1 1 calc R U . . .
C3 C 0.6627(2) 0.4886(4) 0.63097(8) 0.0192(4) Uani 1 1 d . . . . .
H3 H 0.6935 0.6326 0.6157 0.023 Uiso 1 1 calc R U . . .
C4 C 0.5590(2) 0.3486(3) 0.60522(8) 0.0145(4) Uani 1 1 d . . . . .
C5 C 0.5111(2) 0.1383(4) 0.62710(9) 0.0208(4) Uani 1 1 d . . . . .
H5 H 0.4409 0.0441 0.6091 0.025 Uiso 1 1 calc R U . . .
C6 C 0.5682(3) 0.0688(4) 0.67599(10) 0.0257(5) Uani 1 1 d . . . . .
H6 H 0.5353 -0.0727 0.6919 0.031 Uiso 1 1 calc R U . . .
C7 C 0.6629(2) 0.1461(3) 0.49027(8) 0.0159(4) Uani 1 1 d . . . . .
H7A H 0.5752 0.0458 0.4853 0.019 Uiso 1 1 calc R U . . .
H7B H 0.7174 0.0887 0.5217 0.019 Uiso 1 1 calc R U . . .
C8 C 0.7608(2) 0.1327(4) 0.44096(8) 0.0190(4) Uani 1 1 d . . . . .
H8A H 0.8472 0.2354 0.4463 0.023 Uiso 1 1 calc R U . . .
H8B H 0.7970 -0.0299 0.4369 0.023 Uiso 1 1 calc R U . . .
C9 C 0.6835(2) 0.2043(4) 0.39054(8) 0.0174(4) Uani 1 1 d . . . . .
C10 C 0.7154(3) 0.4159(4) 0.36541(9) 0.0236(5) Uani 1 1 d . . . . .
H10 H 0.7893 0.5156 0.3796 0.028 Uiso 1 1 calc R U . . .
C11 C 0.6398(3) 0.4823(4) 0.31978(9) 0.0299(5) Uani 1 1 d . . . . .
H11 H 0.6627 0.6267 0.3029 0.036 Uiso 1 1 calc R U . . .
C12 C 0.5318(3) 0.3399(5) 0.29878(9) 0.0298(5) Uani 1 1 d . . . . .
H12 H 0.4798 0.3870 0.2678 0.036 Uiso 1 1 calc R U . . .
C13 C 0.4997(2) 0.1275(5) 0.32311(10) 0.0284(5) Uani 1 1 d . . . . .
H13 H 0.4260 0.0281 0.3087 0.034 Uiso 1 1 calc R U . . .
C14 C 0.5756(2) 0.0611(4) 0.36848(9) 0.0215(4) Uani 1 1 d . . . . .
H14 H 0.5536 -0.0848 0.3848 0.026 Uiso 1 1 calc R U . . .
H1N H 0.686(3) 0.491(5) 0.5031(11) 0.026(7) Uiso 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
S1 O1 1.4350(13) . ?
S1 O2 1.4409(13) . ?
S1 N1 1.6154(18) . ?
S1 C4 1.769(2) . ?
N1 C7 1.479(2) . ?
N1 H1N 0.86(3) . ?
C1 C6 1.390(3) . ?
C1 C2 1.391(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.383(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.396(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(3) . ?
C5 C6 1.393(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.530(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.507(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C14 1.393(3) . ?
C9 C10 1.394(3) . ?
C10 C11 1.391(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.380(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.389(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.387(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?

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 O2 118.93(8) . . ?
O1 S1 N1 106.74(9) . . ?
O2 S1 N1 107.44(9) . . ?
O1 S1 C4 107.78(10) . . ?
O2 S1 C4 107.56(9) . . ?
N1 S1 C4 107.97(9) . . ?
C7 N1 S1 118.04(13) . . ?
C7 N1 H1N 116(2) . . ?
S1 N1 H1N 108.5(19) . . ?
C6 C1 C2 120.2(2) . . ?
C6 C1 H1 119.9 . . ?
C2 C1 H1 119.9 . . ?
C3 C2 C1 120.2(2) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 119.1(2) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C5 C4 C3 121.5(2) . . ?
C5 C4 S1 120.35(16) . . ?
C3 C4 S1 118.15(16) . . ?
C4 C5 C6 118.6(2) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
C1 C6 C5 120.4(2) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
N1 C7 C8 109.28(16) . . ?
N1 C7 H7A 109.8 . . ?
C8 C7 H7A 109.8 . . ?
N1 C7 H7B 109.8 . . ?
C8 C7 H7B 109.8 . . ?
H7A C7 H7B 108.3 . . ?
C9 C8 C7 113.38(16) . . ?
C9 C8 H8A 108.9 . . ?
C7 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
C7 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
C14 C9 C10 118.3(2) . . ?
C14 C9 C8 120.35(19) . . ?
C10 C9 C8 121.3(2) . . ?
C11 C10 C9 120.5(2) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C12 C11 C10 120.5(2) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 119.7(2) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C14 C13 C12 119.7(2) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C9 121.3(2) . . ?
C13 C14 H14 119.4 . . ?
C9 C14 H14 119.4 . . ?

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
O1 S1 N1 C7 177.04(14) . . . . ?
O2 S1 N1 C7 -54.35(17) . . . . ?
C4 S1 N1 C7 61.40(17) . . . . ?
C6 C1 C2 C3 0.1(4) . . . . ?
C1 C2 C3 C4 -0.9(3) . . . . ?
C2 C3 C4 C5 0.7(3) . . . . ?
C2 C3 C4 S1 -178.07(17) . . . . ?
O1 S1 C4 C5 142.31(16) . . . . ?
O2 S1 C4 C5 12.94(19) . . . . ?
N1 S1 C4 C5 -102.73(18) . . . . ?
O1 S1 C4 C3 -38.89(18) . . . . ?
O2 S1 C4 C3 -168.26(15) . . . . ?
N1 S1 C4 C3 76.07(17) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
S1 C4 C5 C6 179.16(17) . . . . ?
C2 C1 C6 C5 1.1(4) . . . . ?
C4 C5 C6 C1 -1.3(4) . . . . ?
S1 N1 C7 C8 170.12(14) . . . . ?
N1 C7 C8 C9 -62.7(2) . . . . ?
C7 C8 C9 C14 -70.9(2) . . . . ?
C7 C8 C9 C10 107.8(2) . . . . ?
C14 C9 C10 C11 0.7(3) . . . . ?
C8 C9 C10 C11 -178.1(2) . . . . ?
C9 C10 C11 C12 0.2(3) . . . . ?
C10 C11 C12 C13 -0.7(4) . . . . ?
C11 C12 C13 C14 0.4(4) . . . . ?
C12 C13 C14 C9 0.4(3) . . . . ?
C10 C9 C14 C13 -1.0(3) . . . . ?
C8 C9 C14 C13 177.8(2) . . . . ?

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 O1 0.95 2.59 3.293(3) 131.1 1_545
C7 H7B O2 0.99 2.61 3.300(2) 127.3 4
N1 H1N S1 0.86(3) 2.98(3) 3.7075(17) 145(2) 4_565
N1 H1N O2 0.86(3) 2.14(3) 2.980(2) 167(3) 4_565

_refine_diff_density_max         0.313
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_4b
_database_code_depnum_ccdc_archive 'CCDC 2337444'
loop_
_audit_author_name
_audit_author_address
'Rajesh Gonnade'
;CSIR NATIONAL CHEMICAL LABORATORY PUNE INDIA
India
;
_audit_update_record             
;
2024-03-02 deposited with the CCDC.	2024-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H14 Br N O2 S'
_chemical_formula_sum            'C14 H14 Br N O2 S'
_chemical_formula_weight         340.23

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P c'
_space_group_name_Hall           'P -2yc'

_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, z+1/2'

_cell_length_a                   26.8683(14)
_cell_length_b                   5.8303(3)
_cell_length_c                   9.0640(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.976(2)
_cell_angle_gamma                90
_cell_volume                     1402.49(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    9289
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      36.36

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    3.076
_shelx_estimated_absorpt_T_min   0.607
_shelx_estimated_absorpt_T_max   0.813
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6458
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_process_details   'SADABS,(Bruker, 2006)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_source_type              'Incoatech I\mS HB'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            27785
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.302
_diffrn_reflns_theta_max         27.987
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             6645
_reflns_number_gt                6299
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.968
_reflns_Friedel_fraction_max     0.969
_reflns_Friedel_fraction_full    0.972

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;


_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+2.0846P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'direct method'
_atom_sites_solution_secondary   'difference Fourier'
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.041(12)
_chemical_absolute_configuration .
_refine_ls_number_reflns         6645
_refine_ls_number_parameters     352
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0312
_refine_ls_wR_factor_ref         0.0759
_refine_ls_wR_factor_gt          0.0746
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_restrained_S_all      1.101
_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
Br1A Br 0.51766(2) 0.00262(9) 0.23861(5) 0.02364(13) Uani 1 1 d . . . . .
S1A S 0.71945(5) 0.4356(2) 0.60007(13) 0.0134(2) Uani 1 1 d . . . . .
O1A O 0.71497(14) 0.6808(6) 0.6091(4) 0.0191(7) Uani 1 1 d . . . . .
O2A O 0.73207(13) 0.3056(5) 0.7353(3) 0.0185(7) Uani 1 1 d . . . . .
N1A N 0.76131(15) 0.3826(6) 0.4950(4) 0.0152(7) Uani 1 1 d D . . . .
H1NA H 0.758(3) 0.471(11) 0.415(6) 0.05(2) Uiso 1 1 d D . . . .
C1A C 0.57542(17) 0.1388(8) 0.3509(5) 0.0171(9) Uani 1 1 d . . . . .
C2A C 0.60131(18) 0.0192(7) 0.4693(6) 0.0180(9) Uani 1 1 d . . . . .
H2A H 0.589376 -0.125883 0.496240 0.022 Uiso 1 1 calc R U . . .
C3A C 0.6448(2) 0.1110(9) 0.5489(6) 0.0177(10) Uani 1 1 d . . . . .
H3A H 0.663063 0.029499 0.630584 0.021 Uiso 1 1 calc R U . . .
C4A C 0.66146(17) 0.3247(7) 0.5080(5) 0.0139(8) Uani 1 1 d . . . . .
C5A C 0.63488(17) 0.4464(8) 0.3888(5) 0.0168(9) Uani 1 1 d . . . . .
H5A H 0.646537 0.592071 0.361808 0.020 Uiso 1 1 calc R U . . .
C6A C 0.59133(18) 0.3531(8) 0.3100(5) 0.0169(9) Uani 1 1 d . . . . .
H6A H 0.572557 0.434382 0.228975 0.020 Uiso 1 1 calc R U . . .
C7A C 0.76973(17) 0.1401(8) 0.4542(5) 0.0179(9) Uani 1 1 d . . . . .
H7A1 H 0.739753 0.082159 0.387098 0.022 Uiso 1 1 calc R U . . .
H7A2 H 0.774746 0.044099 0.545400 0.022 Uiso 1 1 calc R U . . .
C8A C 0.81524(19) 0.1234(9) 0.3773(6) 0.0214(10) Uani 1 1 d . . . . .
H8A1 H 0.810101 0.224125 0.288301 0.026 Uiso 1 1 calc R U . . .
H8A2 H 0.818081 -0.036057 0.342120 0.026 Uiso 1 1 calc R U . . .
C9A C 0.86410(18) 0.1887(8) 0.4734(5) 0.0190(9) Uani 1 1 d . . . . .
C10A C 0.8852(2) 0.0450(9) 0.5892(6) 0.0245(10) Uani 1 1 d . . . . .
H10A H 0.868980 -0.095834 0.604808 0.029 Uiso 1 1 calc R U . . .
C11A C 0.9291(2) 0.1036(12) 0.6819(7) 0.0304(13) Uani 1 1 d . . . . .
H11A H 0.942844 0.004427 0.761017 0.036 Uiso 1 1 calc R U . . .
C12A C 0.9533(2) 0.3092(12) 0.6586(7) 0.0349(13) Uani 1 1 d . . . . .
H12A H 0.983703 0.349898 0.721280 0.042 Uiso 1 1 calc R U . . .
C13A C 0.9330(2) 0.4522(10) 0.5454(8) 0.0373(14) Uani 1 1 d . . . . .
H13A H 0.949379 0.592519 0.529761 0.045 Uiso 1 1 calc R U . . .
C14A C 0.8885(2) 0.3932(9) 0.4528(6) 0.0283(11) Uani 1 1 d . . . . .
H14A H 0.874642 0.494104 0.374764 0.034 Uiso 1 1 calc R U . . .
Br1B Br 0.47753(2) 0.48376(9) 0.47488(4) 0.02419(14) Uani 1 1 d . . . . .
S1B S 0.27599(5) 0.9338(2) 0.64096(13) 0.0149(2) Uani 1 1 d . . . . .
O1B O 0.26227(14) 0.8034(6) 0.7639(4) 0.0203(7) Uani 1 1 d . . . . .
O2B O 0.28154(14) 1.1768(6) 0.6551(4) 0.0202(7) Uani 1 1 d . . . . .
N1B N 0.23433(15) 0.8878(6) 0.4962(4) 0.0156(7) Uani 1 1 d D . . . .
H1NB H 0.238(3) 0.994(9) 0.433(6) 0.04(2) Uiso 1 1 d D . . . .
C1B C 0.41990(17) 0.6259(8) 0.5306(5) 0.0171(9) Uani 1 1 d . . . . .
C2B C 0.39301(19) 0.5077(8) 0.6247(6) 0.0203(10) Uani 1 1 d . . . . .
H2B H 0.404129 0.361794 0.663266 0.024 Uiso 1 1 calc R U . . .
C3B C 0.3493(2) 0.6063(9) 0.6622(6) 0.0179(10) Uani 1 1 d . . . . .
H3B H 0.330373 0.528728 0.727021 0.021 Uiso 1 1 calc R U . . .
C4B C 0.33380(17) 0.8201(7) 0.6031(5) 0.0148(8) Uani 1 1 d . . . . .
C5B C 0.36082(17) 0.9374(8) 0.5088(5) 0.0173(9) Uani 1 1 d . . . . .
H5B H 0.349551 1.082882 0.469890 0.021 Uiso 1 1 calc R U . . .
C6B C 0.40450(18) 0.8411(8) 0.4713(5) 0.0178(9) Uani 1 1 d . . . . .
H6B H 0.423496 0.919394 0.406904 0.021 Uiso 1 1 calc R U . . .
C7B C 0.22473(18) 0.6466(8) 0.4475(5) 0.0185(9) Uani 1 1 d . . . . .
H7B1 H 0.219477 0.550601 0.533869 0.022 Uiso 1 1 calc R U . . .
H7B2 H 0.254138 0.585582 0.406568 0.022 Uiso 1 1 calc R U . . .
C8B C 0.1778(2) 0.6385(9) 0.3277(6) 0.0231(10) Uani 1 1 d . . . . .
H8B1 H 0.183251 0.738442 0.243374 0.028 Uiso 1 1 calc R U . . .
H8B2 H 0.173090 0.479735 0.289201 0.028 Uiso 1 1 calc R U . . .
C9B C 0.13082(18) 0.7134(8) 0.3837(5) 0.0207(9) Uani 1 1 d . . . . .
C10B C 0.1083(2) 0.9219(10) 0.3413(7) 0.0304(12) Uani 1 1 d . . . . .
H10B H 0.122261 1.017379 0.273299 0.036 Uiso 1 1 calc R U . . .
C11B C 0.0656(2) 0.9930(10) 0.3969(8) 0.0355(14) Uani 1 1 d . . . . .
H11B H 0.050628 1.137026 0.367719 0.043 Uiso 1 1 calc R U . . .
C12B C 0.0446(2) 0.8532(11) 0.4954(7) 0.0353(14) Uani 1 1 d . . . . .
H12B H 0.015302 0.901101 0.533831 0.042 Uiso 1 1 calc R U . . .
C13B C 0.0663(2) 0.6479(13) 0.5360(7) 0.0334(14) Uani 1 1 d . . . . .
H13B H 0.052074 0.552673 0.603700 0.040 Uiso 1 1 calc R U . . .
C14B C 0.10900(19) 0.5744(9) 0.4802(6) 0.0256(10) Uani 1 1 d . . . . .
H14B H 0.123257 0.428697 0.508237 0.031 Uiso 1 1 calc R 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
Br1A C1A 1.892(5) . ?
S1A O2A 1.436(3) . ?
S1A O1A 1.438(3) . ?
S1A N1A 1.613(4) . ?
S1A C4A 1.771(4) . ?
N1A C7A 1.487(6) . ?
N1A H1NA 0.88(3) . ?
C1A C2A 1.374(7) . ?
C1A C6A 1.389(6) . ?
C2A C3A 1.381(7) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.394(6) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.393(6) . ?
C5A C6A 1.384(6) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
C7A C8A 1.502(7) . ?
C7A H7A1 0.9900 . ?
C7A H7A2 0.9900 . ?
C8A C9A 1.506(7) . ?
C8A H8A1 0.9900 . ?
C8A H8A2 0.9900 . ?
C9A C14A 1.387(7) . ?
C9A C10A 1.392(7) . ?
C10A C11A 1.382(8) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.395(9) . ?
C11A H11A 0.9500 . ?
C12A C13A 1.368(9) . ?
C12A H12A 0.9500 . ?
C13A C14A 1.393(8) . ?
C13A H13A 0.9500 . ?
C14A H14A 0.9500 . ?
Br1B C1B 1.893(5) . ?
S1B O2B 1.428(3) . ?
S1B O1B 1.444(3) . ?
S1B N1B 1.609(4) . ?
S1B C4B 1.771(5) . ?
N1B C7B 1.484(6) . ?
N1B H1NB 0.86(3) . ?
C1B C2B 1.384(7) . ?
C1B C6B 1.402(6) . ?
C2B C3B 1.396(8) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.394(7) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.386(6) . ?
C5B C6B 1.390(7) . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
C7B C8B 1.532(6) . ?
C7B H7B1 0.9900 . ?
C7B H7B2 0.9900 . ?
C8B C9B 1.497(7) . ?
C8B H8B1 0.9900 . ?
C8B H8B2 0.9900 . ?
C9B C10B 1.386(7) . ?
C9B C14B 1.388(7) . ?
C10B C11B 1.387(9) . ?
C10B H10B 0.9500 . ?
C11B C12B 1.392(10) . ?
C11B H11B 0.9500 . ?
C12B C13B 1.357(9) . ?
C12B H12B 0.9500 . ?
C13B C14B 1.393(8) . ?
C13B H13B 0.9500 . ?
C14B H14B 0.9500 . ?

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
O2A S1A O1A 119.1(2) . . ?
O2A S1A N1A 108.0(2) . . ?
O1A S1A N1A 107.3(2) . . ?
O2A S1A C4A 106.4(2) . . ?
O1A S1A C4A 108.3(2) . . ?
N1A S1A C4A 107.2(2) . . ?
C7A N1A S1A 118.4(3) . . ?
C7A N1A H1NA 111(5) . . ?
S1A N1A H1NA 112(5) . . ?
C2A C1A C6A 121.7(4) . . ?
C2A C1A Br1A 118.7(3) . . ?
C6A C1A Br1A 119.6(3) . . ?
C1A C2A C3A 119.7(4) . . ?
C1A C2A H2A 120.2 . . ?
C3A C2A H2A 120.2 . . ?
C2A C3A C4A 119.2(4) . . ?
C2A C3A H3A 120.4 . . ?
C4A C3A H3A 120.4 . . ?
C5A C4A C3A 121.0(4) . . ?
C5A C4A S1A 119.1(3) . . ?
C3A C4A S1A 119.8(3) . . ?
C6A C5A C4A 119.3(4) . . ?
C6A C5A H5A 120.3 . . ?
C4A C5A H5A 120.3 . . ?
C5A C6A C1A 119.1(4) . . ?
C5A C6A H6A 120.4 . . ?
C1A C6A H6A 120.4 . . ?
N1A C7A C8A 110.1(4) . . ?
N1A C7A H7A1 109.6 . . ?
C8A C7A H7A1 109.6 . . ?
N1A C7A H7A2 109.6 . . ?
C8A C7A H7A2 109.6 . . ?
H7A1 C7A H7A2 108.2 . . ?
C7A C8A C9A 114.5(4) . . ?
C7A C8A H8A1 108.6 . . ?
C9A C8A H8A1 108.6 . . ?
C7A C8A H8A2 108.6 . . ?
C9A C8A H8A2 108.6 . . ?
H8A1 C8A H8A2 107.6 . . ?
C14A C9A C10A 118.3(5) . . ?
C14A C9A C8A 121.8(4) . . ?
C10A C9A C8A 119.9(4) . . ?
C11A C10A C9A 121.2(5) . . ?
C11A C10A H10A 119.4 . . ?
C9A C10A H10A 119.4 . . ?
C10A C11A C12A 119.6(5) . . ?
C10A C11A H11A 120.2 . . ?
C12A C11A H11A 120.2 . . ?
C13A C12A C11A 119.8(5) . . ?
C13A C12A H12A 120.1 . . ?
C11A C12A H12A 120.1 . . ?
C12A C13A C14A 120.4(5) . . ?
C12A C13A H13A 119.8 . . ?
C14A C13A H13A 119.8 . . ?
C9A C14A C13A 120.7(5) . . ?
C9A C14A H14A 119.7 . . ?
C13A C14A H14A 119.7 . . ?
O2B S1B O1B 119.3(2) . . ?
O2B S1B N1B 106.7(2) . . ?
O1B S1B N1B 108.2(2) . . ?
O2B S1B C4B 107.8(2) . . ?
O1B S1B C4B 106.8(2) . . ?
N1B S1B C4B 107.4(2) . . ?
C7B N1B S1B 117.8(3) . . ?
C7B N1B H1NB 121(5) . . ?
S1B N1B H1NB 106(5) . . ?
C2B C1B C6B 122.0(4) . . ?
C2B C1B Br1B 118.3(3) . . ?
C6B C1B Br1B 119.6(4) . . ?
C1B C2B C3B 119.0(4) . . ?
C1B C2B H2B 120.5 . . ?
C3B C2B H2B 120.5 . . ?
C4B C3B C2B 119.2(5) . . ?
C4B C3B H3B 120.4 . . ?
C2B C3B H3B 120.4 . . ?
C5B C4B C3B 121.6(4) . . ?
C5B C4B S1B 119.6(3) . . ?
C3B C4B S1B 118.6(4) . . ?
C4B C5B C6B 119.7(4) . . ?
C4B C5B H5B 120.2 . . ?
C6B C5B H5B 120.2 . . ?
C5B C6B C1B 118.5(4) . . ?
C5B C6B H6B 120.7 . . ?
C1B C6B H6B 120.7 . . ?
N1B C7B C8B 109.0(4) . . ?
N1B C7B H7B1 109.9 . . ?
C8B C7B H7B1 109.9 . . ?
N1B C7B H7B2 109.9 . . ?
C8B C7B H7B2 109.9 . . ?
H7B1 C7B H7B2 108.3 . . ?
C9B C8B C7B 113.3(4) . . ?
C9B C8B H8B1 108.9 . . ?
C7B C8B H8B1 108.9 . . ?
C9B C8B H8B2 108.9 . . ?
C7B C8B H8B2 108.9 . . ?
H8B1 C8B H8B2 107.7 . . ?
C10B C9B C14B 118.5(5) . . ?
C10B C9B C8B 121.1(5) . . ?
C14B C9B C8B 120.3(5) . . ?
C9B C10B C11B 120.8(6) . . ?
C9B C10B H10B 119.6 . . ?
C11B C10B H10B 119.6 . . ?
C10B C11B C12B 120.0(5) . . ?
C10B C11B H11B 120.0 . . ?
C12B C11B H11B 120.0 . . ?
C13B C12B C11B 119.4(6) . . ?
C13B C12B H12B 120.3 . . ?
C11B C12B H12B 120.3 . . ?
C12B C13B C14B 121.1(6) . . ?
C12B C13B H13B 119.5 . . ?
C14B C13B H13B 119.5 . . ?
C9B C14B C13B 120.2(5) . . ?
C9B C14B H14B 119.9 . . ?
C13B C14B H14B 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2A S1A N1A C7A 56.5(4) . . . . ?
O1A S1A N1A C7A -174.0(3) . . . . ?
C4A S1A N1A C7A -57.8(4) . . . . ?
C6A C1A C2A C3A -1.1(7) . . . . ?
Br1A C1A C2A C3A 177.3(4) . . . . ?
C1A C2A C3A C4A 0.4(7) . . . . ?
C2A C3A C4A C5A 0.2(7) . . . . ?
C2A C3A C4A S1A -175.4(4) . . . . ?
O2A S1A C4A C5A 167.3(3) . . . . ?
O1A S1A C4A C5A 38.1(4) . . . . ?
N1A S1A C4A C5A -77.3(4) . . . . ?
O2A S1A C4A C3A -16.9(4) . . . . ?
O1A S1A C4A C3A -146.1(4) . . . . ?
N1A S1A C4A C3A 98.5(4) . . . . ?
C3A C4A C5A C6A -0.1(7) . . . . ?
S1A C4A C5A C6A 175.6(4) . . . . ?
C4A C5A C6A C1A -0.6(7) . . . . ?
C2A C1A C6A C5A 1.2(7) . . . . ?
Br1A C1A C6A C5A -177.1(4) . . . . ?
S1A N1A C7A C8A -171.1(3) . . . . ?
N1A C7A C8A C9A 64.1(5) . . . . ?
C7A C8A C9A C14A -106.8(6) . . . . ?
C7A C8A C9A C10A 71.3(6) . . . . ?
C14A C9A C10A C11A 0.1(8) . . . . ?
C8A C9A C10A C11A -178.1(5) . . . . ?
C9A C10A C11A C12A -0.6(9) . . . . ?
C10A C11A C12A C13A 0.6(9) . . . . ?
C11A C12A C13A C14A -0.2(10) . . . . ?
C10A C9A C14A C13A 0.3(8) . . . . ?
C8A C9A C14A C13A 178.5(5) . . . . ?
C12A C13A C14A C9A -0.3(9) . . . . ?
O2B S1B N1B C7B 174.4(3) . . . . ?
O1B S1B N1B C7B -56.1(4) . . . . ?
C4B S1B N1B C7B 58.9(4) . . . . ?
C6B C1B C2B C3B -0.2(7) . . . . ?
Br1B C1B C2B C3B -177.5(4) . . . . ?
C1B C2B C3B C4B 0.4(7) . . . . ?
C2B C3B C4B C5B -0.3(7) . . . . ?
C2B C3B C4B S1B 175.6(4) . . . . ?
O2B S1B C4B C5B -39.0(4) . . . . ?
O1B S1B C4B C5B -168.3(3) . . . . ?
N1B S1B C4B C5B 75.7(4) . . . . ?
O2B S1B C4B C3B 145.1(4) . . . . ?
O1B S1B C4B C3B 15.7(4) . . . . ?
N1B S1B C4B C3B -100.2(4) . . . . ?
C3B C4B C5B C6B 0.0(7) . . . . ?
S1B C4B C5B C6B -175.8(3) . . . . ?
C4B C5B C6B C1B 0.1(7) . . . . ?
C2B C1B C6B C5B 0.0(7) . . . . ?
Br1B C1B C6B C5B 177.2(3) . . . . ?
S1B N1B C7B C8B 169.8(3) . . . . ?
N1B C7B C8B C9B -63.4(5) . . . . ?
C7B C8B C9B C10B 107.9(5) . . . . ?
C7B C8B C9B C14B -71.9(6) . . . . ?
C14B C9B C10B C11B 1.6(8) . . . . ?
C8B C9B C10B C11B -178.2(5) . . . . ?
C9B C10B C11B C12B -0.6(9) . . . . ?
C10B C11B C12B C13B 0.0(9) . . . . ?
C11B C12B C13B C14B -0.3(9) . . . . ?
C10B C9B C14B C13B -1.9(8) . . . . ?
C8B C9B C14B C13B 177.9(5) . . . . ?
C12B C13B C14B C9B 1.3(9) . . . . ?

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
_geom_hbond_publ_flag
C3A H3A O1A 0.95 2.49 3.135(6) 125.2 1_545 yes
C7A H7A1 O2A 0.99 2.64 3.330(5) 127.1 2_554 yes
C3B H3B O2B 0.95 2.47 3.091(6) 123.1 1_545 yes
C7B H7B2 O1B 0.99 2.64 3.346(6) 128.7 2_564 yes
N1A H1NA S1A 0.88(3) 2.93(4) 3.734(4) 152(6) 2_564 yes
N1A H1NA O2A 0.88(3) 2.12(3) 2.981(5) 167(8) 2_564 yes
N1B H1NB S1B 0.86(3) 3.01(5) 3.719(4) 141(6) 2_574 yes
N1B H1NB O1B 0.86(3) 2.12(3) 2.955(5) 165(7) 2_574 yes

_refine_diff_density_max         0.974
_refine_diff_density_min         -0.562
_refine_diff_density_rms         0.077

####################################################################### 
# 
# 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_6b
_database_code_depnum_ccdc_archive 'CCDC 2337446'
loop_
_audit_author_name
_audit_author_address
'Rajesh Gonnade'
;CSIR NATIONAL CHEMICAL LABORATORY PUNE INDIA
India
;
_audit_update_record             
;
2024-03-02 deposited with the CCDC.	2024-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H17 N O2 S'
_chemical_formula_sum            'C15 H17 N O2 S'
_chemical_formula_weight         275.35

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/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   15.270(4)
_cell_length_b                   5.4721(15)
_cell_length_c                   17.456(5)
_cell_angle_alpha                90
_cell_angle_beta                 109.587(8)
_cell_angle_gamma                90
_cell_volume                     1374.2(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4686
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      28.65

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.233
_shelx_estimated_absorpt_T_min   0.953
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6458
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   'SADABS (BRUKER, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_source_type              'Incoatech I\mS HB'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            9936
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.406
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.972
_reflns_number_total             2360
_reflns_number_gt                2052
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL, Mercury 2020.20'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1978P)²+11.4293P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'direct method'
_atom_sites_solution_secondary   'difference Fourier'
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2360
_refine_ls_number_parameters     254
_refine_ls_number_restraints     169
_refine_ls_R_factor_all          0.1268
_refine_ls_R_factor_gt           0.1141
_refine_ls_wR_factor_ref         0.3314
_refine_ls_wR_factor_gt          0.3133
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.039
_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
S1 S 0.69169(12) 0.9580(3) 0.62091(10) 0.0159(6) Uani 1 1 d . . . . .
O1 O 0.6323(4) 1.0904(9) 0.5521(3) 0.0229(12) Uani 1 1 d . . . . .
O2 O 0.7523(4) 1.0892(10) 0.6903(3) 0.0260(13) Uani 1 1 d . . . . .
C1 C 0.8583(8) 0.438(2) 0.5206(8) 0.031(4) Uani 0.6 1 d G U P A 1
C2 C 0.8858(7) 0.475(2) 0.6042(7) 0.041(5) Uani 0.6 1 d G U P A 1
H2 H 0.939779 0.395229 0.639140 0.049 Uiso 0.6 1 calc R U P A 1
C3 C 0.8344(10) 0.627(3) 0.6366(5) 0.026(4) Uani 0.6 1 d G U P A 1
H3 H 0.853204 0.652282 0.693658 0.031 Uiso 0.6 1 calc R U P A 1
C4 C 0.7555(9) 0.743(3) 0.5854(7) 0.016(8) Uani 0.4 1 d G U P A 1
C5 C 0.7280(8) 0.707(2) 0.5019(6) 0.033(4) Uani 0.6 1 d G U P A 1
H5 H 0.674047 0.786241 0.466921 0.039 Uiso 0.6 1 calc R U P A 1
C6 C 0.7794(9) 0.554(2) 0.4695(5) 0.042(4) Uani 0.6 1 d G U P A 1
H6 H 0.760621 0.529188 0.412402 0.050 Uiso 0.6 1 calc R U P A 1
C7 C 0.5629(13) 0.635(4) 0.5941(12) 0.016(2) Uani 0.6 1 d . U P B 1
H7A H 0.597050 0.537567 0.565479 0.019 Uiso 0.6 1 calc R U P B 1
H7B H 0.514827 0.733413 0.553617 0.019 Uiso 0.6 1 calc R U P B 1
C8 C 0.5176(10) 0.464(3) 0.6428(11) 0.026(3) Uani 0.7 1 d . U P B 1
H8A H 0.479044 0.341116 0.604731 0.031 Uiso 0.7 1 calc R U P B 1
H8B H 0.568120 0.375113 0.684199 0.031 Uiso 0.7 1 calc R U P B 1
C15 C 0.9100(14) 0.269(4) 0.4839(13) 0.043(5) Uani 0.6 1 d . U P A 1
H15A H 0.974965 0.321695 0.499380 0.064 Uiso 0.6 1 calc R U P A 1
H15B H 0.881630 0.272880 0.424536 0.064 Uiso 0.6 1 calc R U P A 1
H15C H 0.907198 0.102873 0.503593 0.064 Uiso 0.6 1 calc R U P A 1
C1' C 0.8706(10) 0.424(3) 0.5402(10) 0.020(5) Uani 0.4 1 d G U P A 2
C2' C 0.8739(10) 0.442(3) 0.6206(9) 0.021(5) Uani 0.4 1 d G U P A 2
H2' H 0.912867 0.335105 0.660542 0.026 Uiso 0.4 1 calc R U P A 2
C3' C 0.8203(11) 0.616(3) 0.6425(6) 0.027(7) Uani 0.4 1 d G U P A 2
H3' H 0.822538 0.627627 0.697445 0.033 Uiso 0.4 1 calc R U P A 2
C4' C 0.7633(9) 0.772(3) 0.5841(7) 0.014(5) Uani 0.6 1 d G U P A 2
C5' C 0.7600(10) 0.754(2) 0.5037(6) 0.018(4) Uani 0.4 1 d G U P A 2
H5' H 0.721096 0.860774 0.463787 0.021 Uiso 0.4 1 calc R U P A 2
C6' C 0.8137(12) 0.580(3) 0.4818(7) 0.034(5) Uani 0.4 1 d G U P A 2
H6' H 0.811424 0.568254 0.426883 0.041 Uiso 0.4 1 calc R U P A 2
C7' C 0.552(2) 0.615(6) 0.6018(18) 0.016(2) Uani 0.4 1 d . U P B 2
H7'1 H 0.507886 0.716096 0.558763 0.019 Uiso 0.4 1 calc R U P B 2
H7'2 H 0.583722 0.506949 0.574234 0.019 Uiso 0.4 1 calc R U P B 2
C8' C 0.496(3) 0.461(8) 0.632(3) 0.026(3) Uani 0.3 1 d . U P B 2
H8'1 H 0.536685 0.334975 0.666811 0.031 Uiso 0.3 1 calc R U P B 2
H8'2 H 0.450813 0.376032 0.585074 0.031 Uiso 0.3 1 calc R U P B 2
C15' C 0.9300(16) 0.226(4) 0.5170(16) 0.026(5) Uani 0.4 1 d . U P A 2
H15D H 0.991479 0.218289 0.559046 0.039 Uiso 0.4 1 calc R U P A 2
H15E H 0.936762 0.268366 0.464737 0.039 Uiso 0.4 1 calc R U P A 2
H15F H 0.899146 0.067314 0.512626 0.039 Uiso 0.4 1 calc R U P A 2
N1 N 0.6262(4) 0.7916(12) 0.6554(4) 0.0203(14) Uani 1 1 d D . . . .
H1N H 0.654(6) 0.723(16) 0.703(3) 0.03(2) Uiso 1 1 d D . . . .
C9 C 0.4598(7) 0.5835(16) 0.6840(6) 0.017(3) Uani 0.6 1 d G U P B 1
C10 C 0.4378(8) 0.4468(16) 0.7421(7) 0.026(4) Uani 0.5 1 d G U P B 1
H10 H 0.461960 0.286327 0.754996 0.031 Uiso 0.5 1 calc R U P B 1
C11 C 0.3803(9) 0.545(2) 0.7814(7) 0.027(4) Uani 0.45 1 d G U P B 1
H11 H 0.365258 0.451565 0.821162 0.033 Uiso 0.45 1 calc R U P B 1
C12 C 0.3449(9) 0.780(2) 0.7626(7) 0.036(6) Uani 0.45 1 d G U P B 1
H12 H 0.305682 0.846862 0.789438 0.043 Uiso 0.45 1 calc R U P B 1
C13 C 0.3670(9) 0.9164(16) 0.7044(8) 0.028(4) Uani 0.5 1 d G U P B 1
H13 H 0.342807 1.076925 0.691548 0.034 Uiso 0.5 1 calc R U P B 1
C14 C 0.4244(9) 0.8183(16) 0.6651(6) 0.019(3) Uani 0.5 1 d G . P B 1
H14 H 0.439508 0.911691 0.625382 0.022 Uiso 0.5 1 calc R U P B 1
C9' C 0.4422(8) 0.594(2) 0.6810(6) 0.017(5) Uani 0.4 1 d G U P B 2
C10' C 0.4524(7) 0.5394(19) 0.7613(6) 0.022(3) Uani 0.5 1 d G U P B 2
H10' H 0.496628 0.420839 0.790101 0.027 Uiso 0.5 1 calc R U P B 2
C11' C 0.3978(7) 0.658(2) 0.7994(4) 0.029(3) Uani 0.55 1 d G U P B 2
H11' H 0.404747 0.620804 0.854293 0.035 Uiso 0.55 1 calc R U P B 2
C12' C 0.3331(7) 0.832(2) 0.7573(5) 0.025(4) Uani 0.55 1 d G U P B 2
H12' H 0.295760 0.912817 0.783320 0.031 Uiso 0.55 1 calc R U P B 2
C13' C 0.3229(7) 0.8863(18) 0.6770(6) 0.021(3) Uani 0.5 1 d G U P B 2
H13' H 0.278655 1.004871 0.648156 0.025 Uiso 0.5 1 calc R U P B 2
C14' C 0.3775(8) 0.768(2) 0.6388(5) 0.017(3) Uani 0.5 1 d G . P B 2
H14' H 0.370536 0.804908 0.583962 0.021 Uiso 0.5 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
S1 O1 1.435(5) . ?
S1 O2 1.445(5) . ?
S1 N1 1.611(7) . ?
S1 C4 1.765(9) . ?
S1 C4' 1.766(9) . ?
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C1 C15 1.491(19) . ?
C2 C3 1.3900 . ?
C2 H2 0.9500 . ?
C3 C4 1.3900 . ?
C3 H3 0.9500 . ?
C4 C5 1.3900 . ?
C5 C6 1.3900 . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N1 1.46(2) . ?
C7 C8 1.57(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.465(19) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C1' C2' 1.3900 . ?
C1' C6' 1.3900 . ?
C1' C15' 1.55(2) . ?
C2' C3' 1.3900 . ?
C2' H2' 0.9500 . ?
C3' C4' 1.3900 . ?
C3' H3' 0.9500 . ?
C4' C5' 1.3900 . ?
C5' C6' 1.3900 . ?
C5' H5' 0.9500 . ?
C6' H6' 0.9500 . ?
C7' C8' 1.41(5) . ?
C7' N1 1.55(3) . ?
C7' H7'1 0.9900 . ?
C7' H7'2 0.9900 . ?
C8' C9' 1.56(4) . ?
C8' H8'1 0.9900 . ?
C8' H8'2 0.9900 . ?
C15' H15D 0.9800 . ?
C15' H15E 0.9800 . ?
C15' H15F 0.9800 . ?
N1 H1N 0.88(2) . ?
C9 C10 1.3900 . ?
C9 C14 1.3900 . ?
C10 C11 1.3900 . ?
C10 H10 0.9500 . ?
C11 C12 1.3900 . ?
C11 H11 0.9500 . ?
C12 C13 1.3900 . ?
C12 H12 0.9500 . ?
C13 C14 1.3900 . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C9' C10' 1.3900 . ?
C9' C14' 1.3900 . ?
C10' C11' 1.3900 . ?
C10' H10' 0.9500 . ?
C11' C12' 1.3900 . ?
C11' H11' 0.9500 . ?
C12' C13' 1.3900 . ?
C12' H12' 0.9500 . ?
C13' C14' 1.3900 . ?
C13' H13' 0.9500 . ?
C14' H14' 0.9500 . ?

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 O2 119.9(3) . . ?
O1 S1 N1 107.5(3) . . ?
O2 S1 N1 105.7(3) . . ?
O1 S1 C4 108.1(5) . . ?
O2 S1 C4 110.5(5) . . ?
N1 S1 C4 103.9(6) . . ?
O1 S1 C4' 106.3(4) . . ?
O2 S1 C4' 106.9(5) . . ?
N1 S1 C4' 110.3(6) . . ?
C2 C1 C6 120.0 . . ?
C2 C1 C15 121.5(12) . . ?
C6 C1 C15 118.4(12) . . ?
C3 C2 C1 120.0 . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C4 C3 C2 120.0 . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.0 . . ?
C3 C4 S1 122.7(7) . . ?
C5 C4 S1 117.1(7) . . ?
C4 C5 C6 120.0 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 120.0 . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
N1 C7 C8 104.9(13) . . ?
N1 C7 H7A 110.8 . . ?
C8 C7 H7A 110.8 . . ?
N1 C7 H7B 110.8 . . ?
C8 C7 H7B 110.8 . . ?
H7A C7 H7B 108.9 . . ?
C9 C8 C7 116.6(14) . . ?
C9 C8 H8A 108.2 . . ?
C7 C8 H8A 108.2 . . ?
C9 C8 H8B 108.2 . . ?
C7 C8 H8B 108.2 . . ?
H8A C8 H8B 107.3 . . ?
C1 C15 H15A 109.5 . . ?
C1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C2' C1' C6' 120.0 . . ?
C2' C1' C15' 119.1(14) . . ?
C6' C1' C15' 120.9(14) . . ?
C3' C2' C1' 120.0 . . ?
C3' C2' H2' 120.0 . . ?
C1' C2' H2' 120.0 . . ?
C2' C3' C4' 120.0 . . ?
C2' C3' H3' 120.0 . . ?
C4' C3' H3' 120.0 . . ?
C3' C4' C5' 120.0 . . ?
C3' C4' S1 113.5(7) . . ?
C5' C4' S1 126.1(7) . . ?
C6' C5' C4' 120.0 . . ?
C6' C5' H5' 120.0 . . ?
C4' C5' H5' 120.0 . . ?
C5' C6' C1' 120.0 . . ?
C5' C6' H6' 120.0 . . ?
C1' C6' H6' 120.0 . . ?
C8' C7' N1 124(3) . . ?
C8' C7' H7'1 106.3 . . ?
N1 C7' H7'1 106.3 . . ?
C8' C7' H7'2 106.3 . . ?
N1 C7' H7'2 106.3 . . ?
H7'1 C7' H7'2 106.4 . . ?
C7' C8' C9' 115(3) . . ?
C7' C8' H8'1 108.6 . . ?
C9' C8' H8'1 108.6 . . ?
C7' C8' H8'2 108.6 . . ?
C9' C8' H8'2 108.6 . . ?
H8'1 C8' H8'2 107.5 . . ?
C1' C15' H15D 109.5 . . ?
C1' C15' H15E 109.5 . . ?
H15D C15' H15E 109.5 . . ?
C1' C15' H15F 109.5 . . ?
H15D C15' H15F 109.5 . . ?
H15E C15' H15F 109.5 . . ?
C7 N1 S1 113.6(8) . . ?
C7' N1 S1 123.5(11) . . ?
C7 N1 H1N 116(6) . . ?
C7' N1 H1N 109(6) . . ?
S1 N1 H1N 115(6) . . ?
C10 C9 C14 120.0 . . ?
C10 C9 C8 116.8(9) . . ?
C14 C9 C8 123.1(9) . . ?
C11 C10 C9 120.0 . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C12 C11 C10 120.0 . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 120.0 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 120.0 . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C9 120.0 . . ?
C13 C14 H14 120.0 . . ?
C9 C14 H14 120.0 . . ?
C10' C9' C14' 120.0 . . ?
C10' C9' C8' 123.8(16) . . ?
C14' C9' C8' 116.1(16) . . ?
C9' C10' C11' 120.0 . . ?
C9' C10' H10' 120.0 . . ?
C11' C10' H10' 120.0 . . ?
C12' C11' C10' 120.0 . . ?
C12' C11' H11' 120.0 . . ?
C10' C11' H11' 120.0 . . ?
C11' C12' C13' 120.0 . . ?
C11' C12' H12' 120.0 . . ?
C13' C12' H12' 120.0 . . ?
C12' C13' C14' 120.0 . . ?
C12' C13' H13' 120.0 . . ?
C14' C13' H13' 120.0 . . ?
C13' C14' C9' 120.0 . . ?
C13' C14' H14' 120.0 . . ?
C9' C14' H14' 120.0 . . ?

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 0.0 . . . . ?
C15 C1 C2 C3 -178.0(15) . . . . ?
C1 C2 C3 C4 0.0 . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C2 C3 C4 S1 -175.0(12) . . . . ?
O1 S1 C4 C3 164.1(7) . . . . ?
O2 S1 C4 C3 31.1(10) . . . . ?
N1 S1 C4 C3 -81.9(8) . . . . ?
O1 S1 C4 C5 -11.0(9) . . . . ?
O2 S1 C4 C5 -144.0(7) . . . . ?
N1 S1 C4 C5 103.0(8) . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
S1 C4 C5 C6 175.2(12) . . . . ?
C4 C5 C6 C1 0.0 . . . . ?
C2 C1 C6 C5 0.0 . . . . ?
C15 C1 C6 C5 178.1(14) . . . . ?
N1 C7 C8 C9 64.2(16) . . . . ?
C6' C1' C2' C3' 0.0 . . . . ?
C15' C1' C2' C3' -179.1(17) . . . . ?
C1' C2' C3' C4' 0.0 . . . . ?
C2' C3' C4' C5' 0.0 . . . . ?
C2' C3' C4' S1 173.8(11) . . . . ?
O1 S1 C4' C3' -175.0(7) . . . . ?
O2 S1 C4' C3' 55.8(8) . . . . ?
N1 S1 C4' C3' -58.7(8) . . . . ?
O1 S1 C4' C5' -1.7(12) . . . . ?
O2 S1 C4' C5' -130.8(10) . . . . ?
N1 S1 C4' C5' 114.7(11) . . . . ?
C3' C4' C5' C6' 0.0 . . . . ?
S1 C4' C5' C6' -173.0(13) . . . . ?
C4' C5' C6' C1' 0.0 . . . . ?
C2' C1' C6' C5' 0.0 . . . . ?
C15' C1' C6' C5' 179.1(17) . . . . ?
N1 C7' C8' C9' 54(4) . . . . ?
C8 C7 N1 S1 171.8(9) . . . . ?
C8' C7' N1 S1 177(3) . . . . ?
O1 S1 N1 C7 53.8(10) . . . . ?
O2 S1 N1 C7 -177.0(10) . . . . ?
C4 S1 N1 C7 -60.6(11) . . . . ?
O1 S1 N1 C7' 52.3(15) . . . . ?
O2 S1 N1 C7' -178.6(15) . . . . ?
C4' S1 N1 C7' -63.3(15) . . . . ?
C7 C8 C9 C10 -165.2(11) . . . . ?
C7 C8 C9 C14 17.3(17) . . . . ?
C14 C9 C10 C11 0.0 . . . . ?
C8 C9 C10 C11 -177.6(11) . . . . ?
C9 C10 C11 C12 0.0 . . . . ?
C10 C11 C12 C13 0.0 . . . . ?
C11 C12 C13 C14 0.0 . . . . ?
C12 C13 C14 C9 0.0 . . . . ?
C10 C9 C14 C13 0.0 . . . . ?
C8 C9 C14 C13 177.4(12) . . . . ?
C7' C8' C9' C10' -121(3) . . . . ?
C7' C8' C9' C14' 62(3) . . . . ?
C14' C9' C10' C11' 0.0 . . . . ?
C8' C9' C10' C11' -177(2) . . . . ?
C9' C10' C11' C12' 0.0 . . . . ?
C10' C11' C12' C13' 0.0 . . . . ?
C11' C12' C13' C14' 0.0 . . . . ?
C12' C13' C14' C9' 0.0 . . . . ?
C10' C9' C14' C13' 0.0 . . . . ?
C8' C9' C14' C13' 176.8(19) . . . . ?

_refine_diff_density_max         1.599
_refine_diff_density_min         -0.479
_refine_diff_density_rms         0.119

####################################################################### 
# 
# 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_7c
_database_code_depnum_ccdc_archive 'CCDC 2337454'
loop_
_audit_author_name
_audit_author_address
'Rajesh Gonnade'
;CSIR NATIONAL CHEMICAL LABORATORY PUNE INDIA
India
;
_audit_update_record             
;
2024-03-02 deposited with the CCDC.	2024-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H16 N2 O3 S'
_chemical_formula_sum            'C14 H16 N2 O3 S'
_chemical_formula_weight         292.35

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                   7.5399(5)
_cell_length_b                   7.6427(5)
_cell_length_c                   24.2467(16)
_cell_angle_alpha                90
_cell_angle_beta                 93.270(4)
_cell_angle_gamma                90
_cell_volume                     1394.95(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    7437
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      30.70

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.241
_shelx_estimated_absorpt_T_min   0.936
_shelx_estimated_absorpt_T_max   0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6540
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_source_type              'Incoatech I\mS HB'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            19381
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.706
_diffrn_reflns_theta_max         30.731
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4298
_reflns_number_gt                3772
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL, Mercury 2020.20'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0402P)²+0.8654P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'direct method'
_atom_sites_solution_secondary   'difference Fourier'
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4298
_refine_ls_number_parameters     186
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0452
_refine_ls_wR_factor_ref         0.1097
_refine_ls_wR_factor_gt          0.1059
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_restrained_S_all      1.117
_refine_ls_shift/su_max          0.001
_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
S1 S 0.38746(4) 0.67668(4) 0.36596(2) 0.01259(9) Uani 1 1 d . . . . .
O1 O 0.38937(15) 0.84487(14) 0.39278(4) 0.0189(2) Uani 1 1 d . . . . .
O2 O 0.22570(13) 0.61343(15) 0.33864(4) 0.0192(2) Uani 1 1 d . . . . .
O3 O 0.92065(13) 0.68132(13) 0.19744(4) 0.0155(2) Uani 1 1 d . . . . .
N1 N 0.44995(16) 0.53795(15) 0.41338(5) 0.0124(2) Uani 1 1 d . . . . .
H1N H 0.534(3) 0.579(3) 0.4330(10) 0.038(6) Uiso 1 1 d . . . . .
N2 N 0.24494(16) 0.32312(16) 0.52227(5) 0.0145(2) Uani 1 1 d . . . . .
C1 C 0.80391(18) 0.69107(17) 0.23799(6) 0.0117(2) Uani 1 1 d . . . . .
C2 C 0.64799(18) 0.59379(18) 0.22790(6) 0.0134(2) Uani 1 1 d . . . . .
H2 H 0.629021 0.531444 0.194184 0.016 Uiso 1 1 calc R U . . .
C3 C 0.52182(18) 0.58854(18) 0.26700(6) 0.0132(2) Uani 1 1 d . . . . .
H3 H 0.416980 0.520911 0.260539 0.016 Uiso 1 1 calc R U . . .
C4 C 0.54895(18) 0.68300(17) 0.31603(5) 0.0118(2) Uani 1 1 d . . . . .
C5 C 0.70295(18) 0.78112(18) 0.32594(6) 0.0129(2) Uani 1 1 d . . . . .
H5 H 0.720194 0.845271 0.359375 0.016 Uiso 1 1 calc R U . . .
C6 C 0.83191(18) 0.78571(18) 0.28707(6) 0.0127(2) Uani 1 1 d . . . . .
H6 H 0.937398 0.852175 0.293808 0.015 Uiso 1 1 calc R U . . .
C7 C 0.46150(19) 0.35114(18) 0.39916(6) 0.0136(3) Uani 1 1 d . . . . .
H7A H 0.576899 0.327101 0.383151 0.016 Uiso 1 1 calc R U . . .
H7B H 0.365602 0.320795 0.371210 0.016 Uiso 1 1 calc R U . . .
C8 C 0.44405(18) 0.23959(18) 0.45077(6) 0.0137(3) Uani 1 1 d . . . . .
H8A H 0.471577 0.116396 0.441973 0.016 Uiso 1 1 calc R U . . .
H8B H 0.532386 0.279500 0.479843 0.016 Uiso 1 1 calc R U . . .
C9 C 0.26097(18) 0.24841(17) 0.47280(6) 0.0121(2) Uani 1 1 d . . . . .
C10 C 0.11551(19) 0.17827(19) 0.44221(6) 0.0160(3) Uani 1 1 d . . . . .
H10 H 0.130259 0.125721 0.407262 0.019 Uiso 1 1 calc R U . . .
C11 C -0.0511(2) 0.1865(2) 0.46367(6) 0.0189(3) Uani 1 1 d . . . . .
H11 H -0.152044 0.140004 0.443509 0.023 Uiso 1 1 calc R U . . .
C12 C -0.06842(19) 0.2634(2) 0.51486(6) 0.0181(3) Uani 1 1 d . . . . .
H12 H -0.180808 0.270293 0.530556 0.022 Uiso 1 1 calc R U . . .
C13 C 0.0823(2) 0.32984(19) 0.54241(6) 0.0168(3) Uani 1 1 d . . . . .
H13 H 0.070542 0.383062 0.577419 0.020 Uiso 1 1 calc R U . . .
C14 C 1.07585(19) 0.7893(2) 0.20284(7) 0.0194(3) Uani 1 1 d . . . . .
H14A H 1.040309 0.912582 0.203947 0.029 Uiso 1 1 calc R U . . .
H14B H 1.148800 0.769945 0.171225 0.029 Uiso 1 1 calc R U . . .
H14C H 1.144645 0.759448 0.237058 0.029 Uiso 1 1 calc R 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 O2 1.4380(11) . ?
S1 O1 1.4404(11) . ?
S1 N1 1.6145(12) . ?
S1 C4 1.7659(14) . ?
O3 C1 1.3586(16) . ?
O3 C14 1.4320(17) . ?
N1 C7 1.4725(17) . ?
N1 H1N 0.83(2) . ?
N2 C9 1.3400(18) . ?
N2 C13 1.3468(18) . ?
C1 C6 1.3984(19) . ?
C1 C2 1.4006(18) . ?
C2 C3 1.3813(19) . ?
C2 H2 0.9500 . ?
C3 C4 1.3960(19) . ?
C3 H3 0.9500 . ?
C4 C5 1.3916(19) . ?
C5 C6 1.3926(19) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.5259(19) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.5098(19) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.3956(19) . ?
C10 C11 1.388(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.386(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.381(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

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
O2 S1 O1 119.63(7) . . ?
O2 S1 N1 108.23(7) . . ?
O1 S1 N1 105.63(6) . . ?
O2 S1 C4 107.05(6) . . ?
O1 S1 C4 107.19(6) . . ?
N1 S1 C4 108.75(6) . . ?
C1 O3 C14 117.51(11) . . ?
C7 N1 S1 119.26(9) . . ?
C7 N1 H1N 116.3(16) . . ?
S1 N1 H1N 110.1(16) . . ?
C9 N2 C13 118.12(13) . . ?
O3 C1 C6 124.87(12) . . ?
O3 C1 C2 114.62(12) . . ?
C6 C1 C2 120.51(12) . . ?
C3 C2 C1 119.98(13) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 119.76(12) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 120.39(12) . . ?
C5 C4 S1 119.84(10) . . ?
C3 C4 S1 119.76(10) . . ?
C4 C5 C6 120.31(12) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 119.05(12) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 109.92(11) . . ?
N1 C7 H7A 109.7 . . ?
C8 C7 H7A 109.7 . . ?
N1 C7 H7B 109.7 . . ?
C8 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
C9 C8 C7 112.87(11) . . ?
C9 C8 H8A 109.0 . . ?
C7 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
C7 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
N2 C9 C10 122.08(13) . . ?
N2 C9 C8 117.82(12) . . ?
C10 C9 C8 120.10(12) . . ?
C11 C10 C9 118.93(13) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
C12 C11 C10 119.24(14) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C13 C12 C11 118.15(13) . . ?
C13 C12 H12 120.9 . . ?
C11 C12 H12 120.9 . . ?
N2 C13 C12 123.48(14) . . ?
N2 C13 H13 118.3 . . ?
C12 C13 H13 118.3 . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

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
O2 S1 N1 C7 50.53(12) . . . . ?
O1 S1 N1 C7 179.78(10) . . . . ?
C4 S1 N1 C7 -65.44(12) . . . . ?
C14 O3 C1 C6 -6.45(19) . . . . ?
C14 O3 C1 C2 174.77(12) . . . . ?
O3 C1 C2 C3 177.78(12) . . . . ?
C6 C1 C2 C3 -1.1(2) . . . . ?
C1 C2 C3 C4 1.2(2) . . . . ?
C2 C3 C4 C5 -0.5(2) . . . . ?
C2 C3 C4 S1 179.87(10) . . . . ?
O2 S1 C4 C5 162.80(11) . . . . ?
O1 S1 C4 C5 33.28(13) . . . . ?
N1 S1 C4 C5 -80.48(12) . . . . ?
O2 S1 C4 C3 -17.62(13) . . . . ?
O1 S1 C4 C3 -147.13(11) . . . . ?
N1 S1 C4 C3 99.10(12) . . . . ?
C3 C4 C5 C6 -0.2(2) . . . . ?
S1 C4 C5 C6 179.40(10) . . . . ?
C4 C5 C6 C1 0.3(2) . . . . ?
O3 C1 C6 C5 -178.38(12) . . . . ?
C2 C1 C6 C5 0.3(2) . . . . ?
S1 N1 C7 C8 -155.96(10) . . . . ?
N1 C7 C8 C9 67.90(15) . . . . ?
C13 N2 C9 C10 -0.1(2) . . . . ?
C13 N2 C9 C8 -179.35(12) . . . . ?
C7 C8 C9 N2 -113.95(14) . . . . ?
C7 C8 C9 C10 66.79(17) . . . . ?
N2 C9 C10 C11 0.1(2) . . . . ?
C8 C9 C10 C11 179.36(13) . . . . ?
C9 C10 C11 C12 -0.2(2) . . . . ?
C10 C11 C12 C13 0.3(2) . . . . ?
C9 N2 C13 C12 0.2(2) . . . . ?
C11 C12 C13 N2 -0.3(2) . . . . ?

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
_geom_hbond_publ_flag
N1 H1N N2 0.83(2) 2.07(2) 2.9060(17) 176(2) 3_666 yes
C2 H2 O1 0.95 2.54 3.4882(17) 173.4 2_645 yes
C8 H8A O1 0.99 2.46 3.3438(18) 149.1 1_545 yes
C10 H10 O3 0.95 2.58 3.3815(18) 142.1 2_645 yes
C12 H12 O1 0.95 2.65 3.4891(18) 147.2 3_566 yes

_refine_diff_density_max         0.502
_refine_diff_density_min         -0.442
_refine_diff_density_rms         0.068

####################################################################### 
# 
# 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_3b
_database_code_depnum_ccdc_archive 'CCDC 2337443'
loop_
_audit_author_name
_audit_author_address
'Rajesh Gonnade'
;CSIR NATIONAL CHEMICAL LABORATORY PUNE INDIA
India
;
_audit_update_record             
;
2024-03-02 deposited with the CCDC.	2024-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H14 Cl N O2 S'
_chemical_formula_sum            'C14 H14 Cl N O2 S'
_chemical_formula_weight         295.77

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P c'
_space_group_name_Hall           'P -2yc'

_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, z+1/2'

_cell_length_a                   26.5795(11)
_cell_length_b                   5.7691(2)
_cell_length_c                   9.0833(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.9910(10)
_cell_angle_gamma                90
_cell_volume                     1375.72(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8630
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      31.82

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.426
_shelx_estimated_absorpt_T_min   0.890
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6518
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_source_type              'Incoatech I\mS HB'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            15835
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.327
_diffrn_reflns_theta_max         31.841
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_point_group_measured_fraction_full 0.954
_reflns_number_total             8669
_reflns_number_gt                7973
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.852
_reflns_Friedel_fraction_max     0.847
_reflns_Friedel_fraction_full    0.914

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL, Mercury 2020.20'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0343P)²+0.3674P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'direct method'
_atom_sites_solution_secondary   'difference Fourier'
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.00(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         8669
_refine_ls_number_parameters     352
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0335
_refine_ls_wR_factor_ref         0.0783
_refine_ls_wR_factor_gt          0.0759
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.001
_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
Cl1A Cl 0.48339(3) 0.02084(12) 0.53700(6) 0.02391(13) Uani 1 1 d . . . . .
S1A S 0.28337(2) 0.43505(10) 0.18054(5) 0.01399(11) Uani 1 1 d . . . . .
O1A O 0.27079(7) 0.3022(3) 0.04542(17) 0.0179(3) Uani 1 1 d . . . . .
O2A O 0.28774(7) 0.6825(3) 0.17046(19) 0.0192(3) Uani 1 1 d . . . . .
N1A N 0.24078(7) 0.3832(4) 0.2846(2) 0.0152(3) Uani 1 1 d . . . . .
H1NA H 0.2439(15) 0.483(7) 0.355(5) 0.038(10) Uiso 1 1 d . . . . .
C1A C 0.42925(9) 0.1416(4) 0.4330(2) 0.0175(4) Uani 1 1 d . . . . .
C2A C 0.40402(9) 0.0192(4) 0.3125(3) 0.0183(4) Uani 1 1 d . . . . .
H2A H 0.416837 -0.125671 0.285163 0.022 Uiso 1 1 calc R U . . .
C3A C 0.35965(10) 0.1111(4) 0.2318(3) 0.0178(4) Uani 1 1 d . . . . .
H3A H 0.341692 0.029170 0.149154 0.021 Uiso 1 1 calc R U . . .
C4A C 0.34193(8) 0.3243(4) 0.2736(2) 0.0143(4) Uani 1 1 d . . . . .
C5A C 0.36793(9) 0.4483(4) 0.3939(2) 0.0168(4) Uani 1 1 d . . . . .
H5A H 0.355425 0.594281 0.420452 0.020 Uiso 1 1 calc R U . . .
C6A C 0.41221(9) 0.3571(4) 0.4747(3) 0.0184(4) Uani 1 1 d . . . . .
H6A H 0.430490 0.439692 0.556527 0.022 Uiso 1 1 calc R U . . .
C7A C 0.23238(9) 0.1388(4) 0.3255(2) 0.0168(4) Uani 1 1 d . . . . .
H7A1 H 0.262769 0.080058 0.392014 0.020 Uiso 1 1 calc R U . . .
H7A2 H 0.227015 0.041517 0.234584 0.020 Uiso 1 1 calc R U . . .
C8A C 0.18589(9) 0.1236(5) 0.4043(3) 0.0203(4) Uani 1 1 d . . . . .
H8A1 H 0.182990 -0.036799 0.440765 0.024 Uiso 1 1 calc R U . . .
H8A2 H 0.191122 0.227324 0.492196 0.024 Uiso 1 1 calc R U . . .
C9A C 0.13665(9) 0.1885(4) 0.3071(3) 0.0183(4) Uani 1 1 d . . . . .
C10A C 0.11542(10) 0.0435(5) 0.1913(3) 0.0227(5) Uani 1 1 d . . . . .
H10A H 0.131924 -0.098203 0.175264 0.027 Uiso 1 1 calc R U . . .
C11A C 0.07035(11) 0.1025(6) 0.0986(3) 0.0277(6) Uani 1 1 d . . . . .
H11A H 0.056419 0.002486 0.019528 0.033 Uiso 1 1 calc R U . . .
C12A C 0.04605(11) 0.3090(5) 0.1229(3) 0.0302(6) Uani 1 1 d . . . . .
H12A H 0.015472 0.351347 0.059858 0.036 Uiso 1 1 calc R U . . .
C13A C 0.06635(11) 0.4529(5) 0.2387(4) 0.0324(6) Uani 1 1 d . . . . .
H13A H 0.049352 0.592732 0.256122 0.039 Uiso 1 1 calc R U . . .
C14A C 0.11163(10) 0.3937(5) 0.3301(3) 0.0261(5) Uani 1 1 d . . . . .
H14A H 0.125513 0.494467 0.408775 0.031 Uiso 1 1 calc R U . . .
Cl1B Cl 0.51830(3) 0.49367(12) 0.80475(7) 0.02529(14) Uani 1 1 d . . . . .
S1B S 0.71838(2) 0.06597(10) 0.63936(5) 0.01424(11) Uani 1 1 d . . . . .
O1B O 0.73184(7) 0.1997(3) 0.51676(17) 0.0186(3) Uani 1 1 d . . . . .
O2B O 0.71318(7) -0.1807(3) 0.62347(19) 0.0191(3) Uani 1 1 d . . . . .
N1B N 0.76089(7) 0.1131(3) 0.7832(2) 0.0150(3) Uani 1 1 d . . . . .
H1NB H 0.7558(13) 0.018(6) 0.845(4) 0.021(8) Uiso 1 1 d . . . . .
C1B C 0.57262(9) 0.3687(4) 0.7537(3) 0.0185(4) Uani 1 1 d . . . . .
C2B C 0.59864(9) 0.4881(4) 0.6565(3) 0.0193(4) Uani 1 1 d . . . . .
H2B H 0.586401 0.633317 0.616529 0.023 Uiso 1 1 calc R U . . .
C3B C 0.64293(10) 0.3924(5) 0.6181(3) 0.0187(5) Uani 1 1 d . . . . .
H3B H 0.661287 0.471825 0.551786 0.022 Uiso 1 1 calc R U . . .
C4B C 0.65994(8) 0.1799(4) 0.6778(2) 0.0146(4) Uani 1 1 d . . . . .
C5B C 0.63346(9) 0.0594(4) 0.7747(2) 0.0170(4) Uani 1 1 d . . . . .
H5B H 0.645643 -0.086138 0.814325 0.020 Uiso 1 1 calc R U . . .
C6B C 0.58911(9) 0.1538(4) 0.8129(3) 0.0191(4) Uani 1 1 d . . . . .
H6B H 0.570413 0.073430 0.877916 0.023 Uiso 1 1 calc R U . . .
C7B C 0.77051(9) 0.3550(4) 0.8330(3) 0.0180(4) Uani 1 1 d . . . . .
H7B1 H 0.740607 0.415904 0.873324 0.022 Uiso 1 1 calc R U . . .
H7B2 H 0.775978 0.452954 0.747425 0.022 Uiso 1 1 calc R U . . .
C8B C 0.81757(10) 0.3640(5) 0.9533(3) 0.0205(4) Uani 1 1 d . . . . .
H8B1 H 0.822273 0.524678 0.991169 0.025 Uiso 1 1 calc R U . . .
H8B2 H 0.811797 0.263736 1.037585 0.025 Uiso 1 1 calc R U . . .
C9B C 0.86562(9) 0.2864(4) 0.8981(3) 0.0189(4) Uani 1 1 d . . . . .
C10B C 0.88772(9) 0.4255(5) 0.7998(3) 0.0223(5) Uani 1 1 d . . . . .
H10B H 0.872928 0.571428 0.770192 0.027 Uiso 1 1 calc R U . . .
C11B C 0.93098(11) 0.3534(6) 0.7448(3) 0.0289(6) Uani 1 1 d . . . . .
H11B H 0.945400 0.448771 0.676994 0.035 Uiso 1 1 calc R U . . .
C12B C 0.95315(11) 0.1420(6) 0.7890(3) 0.0317(6) Uani 1 1 d . . . . .
H12B H 0.982812 0.092423 0.751581 0.038 Uiso 1 1 calc R U . . .
C13B C 0.93207(11) 0.0034(5) 0.8874(4) 0.0307(6) Uani 1 1 d . . . . .
H13B H 0.947292 -0.141316 0.917757 0.037 Uiso 1 1 calc R U . . .
C14B C 0.88847(10) 0.0757(5) 0.9421(3) 0.0251(5) Uani 1 1 d . . . . .
H14B H 0.874266 -0.019974 1.010173 0.030 Uiso 1 1 calc R 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
Cl1A C1A 1.739(2) . ?
S1A O2A 1.4365(18) . ?
S1A O1A 1.4414(16) . ?
S1A N1A 1.612(2) . ?
S1A C4A 1.770(2) . ?
N1A C7A 1.484(3) . ?
N1A H1NA 0.86(4) . ?
C1A C2A 1.385(3) . ?
C1A C6A 1.396(3) . ?
C2A C3A 1.393(4) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.391(3) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.396(3) . ?
C5A C6A 1.389(3) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
C7A C8A 1.524(3) . ?
C7A H7A1 0.9900 . ?
C7A H7A2 0.9900 . ?
C8A C9A 1.507(3) . ?
C8A H8A1 0.9900 . ?
C8A H8A2 0.9900 . ?
C9A C14A 1.390(4) . ?
C9A C10A 1.392(3) . ?
C10A C11A 1.395(4) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.389(4) . ?
C11A H11A 0.9500 . ?
C12A C13A 1.382(4) . ?
C12A H12A 0.9500 . ?
C13A C14A 1.394(4) . ?
C13A H13A 0.9500 . ?
C14A H14A 0.9500 . ?
Cl1B C1B 1.740(2) . ?
S1B O2B 1.4346(18) . ?
S1B O1B 1.4448(16) . ?
S1B N1B 1.6109(19) . ?
S1B C4B 1.771(2) . ?
N1B C7B 1.477(3) . ?
N1B H1NB 0.81(3) . ?
C1B C2B 1.387(3) . ?
C1B C6B 1.394(3) . ?
C2B C3B 1.393(4) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.387(3) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.396(3) . ?
C5B C6B 1.391(3) . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
C7B C8B 1.528(3) . ?
C7B H7B1 0.9900 . ?
C7B H7B2 0.9900 . ?
C8B C9B 1.511(3) . ?
C8B H8B1 0.9900 . ?
C8B H8B2 0.9900 . ?
C9B C14B 1.389(4) . ?
C9B C10B 1.396(3) . ?
C10B C11B 1.387(4) . ?
C10B H10B 0.9500 . ?
C11B C12B 1.386(5) . ?
C11B H11B 0.9500 . ?
C12B C13B 1.381(5) . ?
C12B H12B 0.9500 . ?
C13B C14B 1.394(4) . ?
C13B H13B 0.9500 . ?
C14B H14B 0.9500 . ?

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
O2A S1A O1A 118.99(10) . . ?
O2A S1A N1A 107.03(11) . . ?
O1A S1A N1A 108.05(10) . . ?
O2A S1A C4A 108.38(10) . . ?
O1A S1A C4A 106.52(10) . . ?
N1A S1A C4A 107.37(10) . . ?
C7A N1A S1A 118.04(15) . . ?
C7A N1A H1NA 117(3) . . ?
S1A N1A H1NA 109(3) . . ?
C2A C1A C6A 122.1(2) . . ?
C2A C1A Cl1A 118.84(19) . . ?
C6A C1A Cl1A 119.07(18) . . ?
C1A C2A C3A 119.2(2) . . ?
C1A C2A H2A 120.4 . . ?
C3A C2A H2A 120.4 . . ?
C4A C3A C2A 119.2(2) . . ?
C4A C3A H3A 120.4 . . ?
C2A C3A H3A 120.4 . . ?
C3A C4A C5A 121.3(2) . . ?
C3A C4A S1A 119.89(17) . . ?
C5A C4A S1A 118.67(17) . . ?
C6A C5A C4A 119.6(2) . . ?
C6A C5A H5A 120.2 . . ?
C4A C5A H5A 120.2 . . ?
C5A C6A C1A 118.6(2) . . ?
C5A C6A H6A 120.7 . . ?
C1A C6A H6A 120.7 . . ?
N1A C7A C8A 109.70(19) . . ?
N1A C7A H7A1 109.7 . . ?
C8A C7A H7A1 109.7 . . ?
N1A C7A H7A2 109.7 . . ?
C8A C7A H7A2 109.7 . . ?
H7A1 C7A H7A2 108.2 . . ?
C9A C8A C7A 113.82(18) . . ?
C9A C8A H8A1 108.8 . . ?
C7A C8A H8A1 108.8 . . ?
C9A C8A H8A2 108.8 . . ?
C7A C8A H8A2 108.8 . . ?
H8A1 C8A H8A2 107.7 . . ?
C14A C9A C10A 118.6(2) . . ?
C14A C9A C8A 121.0(2) . . ?
C10A C9A C8A 120.4(2) . . ?
C9A C10A C11A 121.2(3) . . ?
C9A C10A H10A 119.4 . . ?
C11A C10A H10A 119.4 . . ?
C12A C11A C10A 119.3(3) . . ?
C12A C11A H11A 120.3 . . ?
C10A C11A H11A 120.3 . . ?
C13A C12A C11A 120.0(3) . . ?
C13A C12A H12A 120.0 . . ?
C11A C12A H12A 120.0 . . ?
C12A C13A C14A 120.3(3) . . ?
C12A C13A H13A 119.9 . . ?
C14A C13A H13A 119.9 . . ?
C9A C14A C13A 120.5(2) . . ?
C9A C14A H14A 119.7 . . ?
C13A C14A H14A 119.7 . . ?
O2B S1B O1B 118.91(10) . . ?
O2B S1B N1B 107.05(11) . . ?
O1B S1B N1B 107.95(10) . . ?
O2B S1B C4B 108.32(11) . . ?
O1B S1B C4B 106.51(11) . . ?
N1B S1B C4B 107.65(10) . . ?
C7B N1B S1B 118.28(15) . . ?
C7B N1B H1NB 118(2) . . ?
S1B N1B H1NB 106(2) . . ?
C2B C1B C6B 121.9(2) . . ?
C2B C1B Cl1B 118.74(19) . . ?
C6B C1B Cl1B 119.31(19) . . ?
C1B C2B C3B 119.2(2) . . ?
C1B C2B H2B 120.4 . . ?
C3B C2B H2B 120.4 . . ?
C4B C3B C2B 119.3(2) . . ?
C4B C3B H3B 120.4 . . ?
C2B C3B H3B 120.4 . . ?
C3B C4B C5B 121.4(2) . . ?
C3B C4B S1B 119.56(18) . . ?
C5B C4B S1B 118.93(18) . . ?
C6B C5B C4B 119.5(2) . . ?
C6B C5B H5B 120.2 . . ?
C4B C5B H5B 120.2 . . ?
C5B C6B C1B 118.7(2) . . ?
C5B C6B H6B 120.7 . . ?
C1B C6B H6B 120.7 . . ?
N1B C7B C8B 109.53(19) . . ?
N1B C7B H7B1 109.8 . . ?
C8B C7B H7B1 109.8 . . ?
N1B C7B H7B2 109.8 . . ?
C8B C7B H7B2 109.8 . . ?
H7B1 C7B H7B2 108.2 . . ?
C9B C8B C7B 113.11(19) . . ?
C9B C8B H8B1 109.0 . . ?
C7B C8B H8B1 109.0 . . ?
C9B C8B H8B2 109.0 . . ?
C7B C8B H8B2 109.0 . . ?
H8B1 C8B H8B2 107.8 . . ?
C14B C9B C10B 118.6(2) . . ?
C14B C9B C8B 121.2(2) . . ?
C10B C9B C8B 120.3(2) . . ?
C11B C10B C9B 120.9(3) . . ?
C11B C10B H10B 119.6 . . ?
C9B C10B H10B 119.6 . . ?
C12B C11B C10B 119.9(3) . . ?
C12B C11B H11B 120.1 . . ?
C10B C11B H11B 120.1 . . ?
C13B C12B C11B 120.0(3) . . ?
C13B C12B H12B 120.0 . . ?
C11B C12B H12B 120.0 . . ?
C12B C13B C14B 120.1(3) . . ?
C12B C13B H13B 120.0 . . ?
C14B C13B H13B 120.0 . . ?
C9B C14B C13B 120.6(3) . . ?
C9B C14B H14B 119.7 . . ?
C13B C14B H14B 119.7 . . ?

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
O2A S1A N1A C7A -174.13(16) . . . . ?
O1A S1A N1A C7A 56.61(18) . . . . ?
C4A S1A N1A C7A -57.94(18) . . . . ?
C6A C1A C2A C3A -1.4(4) . . . . ?
Cl1A C1A C2A C3A 177.80(18) . . . . ?
C1A C2A C3A C4A 0.4(4) . . . . ?
C2A C3A C4A C5A 0.5(3) . . . . ?
C2A C3A C4A S1A -175.76(18) . . . . ?
O2A S1A C4A C3A -144.53(19) . . . . ?
O1A S1A C4A C3A -15.4(2) . . . . ?
N1A S1A C4A C3A 100.2(2) . . . . ?
O2A S1A C4A C5A 39.1(2) . . . . ?
O1A S1A C4A C5A 168.26(17) . . . . ?
N1A S1A C4A C5A -76.18(19) . . . . ?
C3A C4A C5A C6A -0.5(3) . . . . ?
S1A C4A C5A C6A 175.79(18) . . . . ?
C4A C5A C6A C1A -0.4(3) . . . . ?
C2A C1A C6A C5A 1.3(4) . . . . ?
Cl1A C1A C6A C5A -177.82(18) . . . . ?
S1A N1A C7A C8A -171.89(15) . . . . ?
N1A C7A C8A C9A 64.7(3) . . . . ?
C7A C8A C9A C14A -109.0(3) . . . . ?
C7A C8A C9A C10A 70.6(3) . . . . ?
C14A C9A C10A C11A 0.8(4) . . . . ?
C8A C9A C10A C11A -178.9(2) . . . . ?
C9A C10A C11A C12A -0.5(4) . . . . ?
C10A C11A C12A C13A -0.5(5) . . . . ?
C11A C12A C13A C14A 1.0(5) . . . . ?
C10A C9A C14A C13A -0.2(4) . . . . ?
C8A C9A C14A C13A 179.5(2) . . . . ?
C12A C13A C14A C9A -0.7(5) . . . . ?
O2B S1B N1B C7B -174.67(17) . . . . ?
O1B S1B N1B C7B 56.21(19) . . . . ?
C4B S1B N1B C7B -58.40(19) . . . . ?
C6B C1B C2B C3B -0.9(4) . . . . ?
Cl1B C1B C2B C3B 178.28(18) . . . . ?
C1B C2B C3B C4B 0.1(3) . . . . ?
C2B C3B C4B C5B 0.4(3) . . . . ?
C2B C3B C4B S1B -175.89(18) . . . . ?
O2B S1B C4B C3B -143.24(18) . . . . ?
O1B S1B C4B C3B -14.2(2) . . . . ?
N1B S1B C4B C3B 101.32(19) . . . . ?
O2B S1B C4B C5B 40.4(2) . . . . ?
O1B S1B C4B C5B 169.38(17) . . . . ?
N1B S1B C4B C5B -75.1(2) . . . . ?
C3B C4B C5B C6B -0.1(3) . . . . ?
S1B C4B C5B C6B 176.17(17) . . . . ?
C4B C5B C6B C1B -0.6(3) . . . . ?
C2B C1B C6B C5B 1.1(3) . . . . ?
Cl1B C1B C6B C5B -178.02(18) . . . . ?
S1B N1B C7B C8B -170.81(16) . . . . ?
N1B C7B C8B C9B 62.7(3) . . . . ?
C7B C8B C9B C14B -108.2(3) . . . . ?
C7B C8B C9B C10B 71.1(3) . . . . ?
C14B C9B C10B C11B 1.2(4) . . . . ?
C8B C9B C10B C11B -178.1(2) . . . . ?
C9B C10B C11B C12B -0.8(4) . . . . ?
C10B C11B C12B C13B 0.1(4) . . . . ?
C11B C12B C13B C14B 0.1(4) . . . . ?
C10B C9B C14B C13B -1.0(4) . . . . ?
C8B C9B C14B C13B 178.3(2) . . . . ?
C12B C13B C14B C9B 0.3(4) . . . . ?

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
_geom_hbond_publ_flag
N1A H1NA S1A 0.86(4) 3.02(4) 3.7475(19) 145(3) 2_565 yes
N1A H1NA O1A 0.86(4) 2.16(4) 2.992(3) 165(4) 2_565 yes
C3A H3A O2A 0.95 2.49 3.121(3) 124.3 1_545 yes
C7A H7A1 O1A 0.99 2.60 3.297(3) 127.5 2 yes
N1B H1NB S1B 0.81(3) 3.03(4) 3.736(2) 146(3) 2 yes
N1B H1NB O1B 0.81(3) 2.17(3) 2.978(3) 170(3) 2 yes
C3B H3B O2B 0.95 2.46 3.087(3) 123.1 1_565 yes
C6B H6B Cl1A 0.95 2.96 3.853(2) 156.5 2 yes
C7B H7B1 O1B 0.99 2.60 3.313(3) 128.9 2_565 yes

_refine_diff_density_max         0.456
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_2b
_database_code_depnum_ccdc_archive 'CCDC 2337442'
loop_
_audit_author_name
_audit_author_address
'Rajesh Gonnade'
;CSIR NATIONAL CHEMICAL LABORATORY PUNE INDIA
India
;
_audit_update_record             
;
2024-03-02 deposited with the CCDC.	2024-05-27 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_DIFMN02_2b                  
;
PROBLEM: The minimum difference density is < -0.1*ZMAX*1.00
RESPONSE: This eoor is attributed to the poor quality of the diffraction data 
that leading to spurious peaks and holes of residual electron density.
;
_vrf_PLAT098_2b                  
;
PROBLEM: Large Reported Min.  (Negative) Residual Density      -1.64 eA-3  
RESPONSE: This eoor is attributed to the poor quality of the diffraction data 
that leading to spurious residual electron density peaks and holes close to the S-atom.
;
_vrf_PLAT340_2b                  
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............     0.0166 Ang.  
RESPONSE: This eoor is attributed to the poor quality of the diffraction data.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H14 N2 O2 S'
_chemical_formula_sum            'C15 H14 N2 O2 S'
_chemical_formula_weight         286.34

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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

_cell_length_a                   9.1812(6)
_cell_length_b                   5.7173(4)
_cell_length_c                   53.186(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2791.8(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9902
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      30.44

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_F_000             1200
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.234
_shelx_estimated_absorpt_T_min   0.946
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6139
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_source_type              'Incoatech I\mS HB'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            16364
_diffrn_reflns_av_unetI/netI     0.0557
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -63
_diffrn_reflns_limit_l_max       62
_diffrn_reflns_theta_min         3.064
_diffrn_reflns_theta_max         24.993
_diffrn_reflns_theta_full        24.993
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.962
_reflns_number_total             4735
_reflns_number_gt                4570
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.904
_reflns_Friedel_fraction_max     0.925
_reflns_Friedel_fraction_full    0.925

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL, Mercury 2020.20'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0001P)²+25.2577P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'direct method'
_atom_sites_solution_secondary   'difference Fourier'
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.3(3)
_chemical_absolute_configuration .
_refine_ls_number_reflns         4735
_refine_ls_number_parameters     362
_refine_ls_number_restraints     145
_refine_ls_R_factor_all          0.0903
_refine_ls_R_factor_gt           0.0886
_refine_ls_wR_factor_ref         0.2042
_refine_ls_wR_factor_gt          0.2034
_refine_ls_goodness_of_fit_ref   1.172
_refine_ls_restrained_S_all      1.166
_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
S1A S -0.0328(3) 0.0658(5) 0.60988(5) 0.0166(6) Uani 1 1 d . . . . .
O1A O -0.1610(8) 0.2034(14) 0.61673(15) 0.0215(18) Uani 1 1 d . U . . .
O2A O -0.0419(9) -0.1805(14) 0.60742(16) 0.0221(18) Uani 1 1 d . U . . .
N1A N 0.0922(10) 0.1135(18) 0.63048(17) 0.019(2) Uani 1 1 d . U . . .
H1A H 0.133569 -0.003087 0.638595 0.023 Uiso 1 1 calc R U . . .
N2A N 0.2509(11) 0.547(2) 0.4959(2) 0.033(3) Uani 1 1 d . . . . .
C1A C 0.1461(13) 0.363(2) 0.5371(2) 0.021(3) Uani 1 1 d . U . . .
C2A C 0.1991(13) 0.151(2) 0.5464(2) 0.021(2) Uani 1 1 d . U . . .
H2A H 0.273480 0.070371 0.537484 0.025 Uiso 1 1 calc R U . . .
C3A C 0.1441(12) 0.056(2) 0.5686(2) 0.021(3) Uani 1 1 d . U . . .
H3A H 0.180778 -0.085665 0.575377 0.025 Uiso 1 1 calc R U . . .
C4A C 0.0294(12) 0.1839(19) 0.5808(2) 0.016(2) Uani 1 1 d . U . . .
C5A C -0.0239(13) 0.391(2) 0.5717(2) 0.022(3) Uani 1 1 d . U . . .
H5A H -0.099396 0.470212 0.580418 0.027 Uiso 1 1 calc R U . . .
C6A C 0.0338(12) 0.485(2) 0.5493(2) 0.019(2) Uani 1 1 d . U . . .
H6A H -0.002532 0.627255 0.542671 0.023 Uiso 1 1 calc R U . . .
C7A C 0.1348(12) 0.353(2) 0.6353(2) 0.021(3) Uani 1 1 d . . . . .
H7AA H 0.046692 0.450257 0.637831 0.025 Uiso 1 1 calc R U . . .
H7AB H 0.188213 0.415487 0.620593 0.025 Uiso 1 1 calc R U . . .
C8A C 0.2327(13) 0.368(3) 0.6589(2) 0.027(3) Uani 1 1 d . . . . .
H8AA H 0.321522 0.273608 0.656092 0.033 Uiso 1 1 calc R U . . .
H8AB H 0.263434 0.532741 0.661359 0.033 Uiso 1 1 calc R U . . .
C9A C 0.1575(13) 0.283(2) 0.6827(2) 0.026(3) Uani 1 1 d . . . . .
C10A C 0.1930(15) 0.072(2) 0.6941(2) 0.031(3) Uani 1 1 d . U . . .
H10A H 0.267998 -0.023309 0.687361 0.037 Uiso 1 1 calc R U . . .
C11A C 0.1172(15) 0.003(3) 0.7156(3) 0.035(3) Uani 1 1 d . U . . .
H11A H 0.141521 -0.141878 0.723410 0.042 Uiso 1 1 calc R U . . .
C12A C 0.0079(16) 0.138(3) 0.7259(3) 0.037(3) Uani 1 1 d . . . . .
H12A H -0.044354 0.085496 0.740192 0.045 Uiso 1 1 calc R U . . .
C13A C -0.0259(14) 0.357(3) 0.7148(2) 0.029(3) Uani 1 1 d . . . . .
H13A H -0.099567 0.454498 0.721803 0.035 Uiso 1 1 calc R U . . .
C14A C 0.0527(13) 0.429(3) 0.6931(2) 0.029(3) Uani 1 1 d . . . . .
H14A H 0.033353 0.576812 0.685633 0.035 Uiso 1 1 calc R U . . .
C15A C 0.2052(12) 0.464(2) 0.5141(2) 0.020(2) Uani 1 1 d . U . . .
S1B S 0.7506(3) 0.5656(5) 0.38954(5) 0.0172(6) Uani 1 1 d . . . . .
O1B O 0.7675(8) 0.3155(13) 0.39194(16) 0.0206(17) Uani 1 1 d . U . . .
O2B O 0.8780(8) 0.6967(13) 0.38312(13) 0.0149(16) Uani 1 1 d . U . . .
N1B N 0.6265(10) 0.6150(17) 0.36898(17) 0.017(2) Uani 1 1 d . U . . .
H1B H 0.585315 0.499891 0.360616 0.020 Uiso 1 1 calc R U . . .
N2B N 0.4652(11) 1.043(2) 0.5034(2) 0.030(3) Uani 1 1 d . . . . .
C1B C 0.5697(12) 0.863(2) 0.4624(2) 0.017(2) Uani 1 1 d . U . . .
C2B C 0.6815(12) 0.977(2) 0.4499(2) 0.020(2) Uani 1 1 d . U . . .
H2B H 0.719175 1.118252 0.456678 0.023 Uiso 1 1 calc R U . . .
C3B C 0.7387(13) 0.892(2) 0.4280(2) 0.020(3) Uani 1 1 d . U . . .
H3B H 0.813091 0.975298 0.419382 0.024 Uiso 1 1 calc R U . . .
C4B C 0.6852(12) 0.6796(19) 0.4186(2) 0.015(2) Uani 1 1 d . U . . .
C5B C 0.5767(11) 0.560(2) 0.4315(2) 0.016(2) Uani 1 1 d . U . . .
H5B H 0.543074 0.414429 0.425155 0.019 Uiso 1 1 calc R U . . .
C6B C 0.5164(12) 0.649(2) 0.4534(2) 0.019(2) Uani 1 1 d . U . . .
H6B H 0.441167 0.568038 0.461960 0.023 Uiso 1 1 calc R U . . .
C7B C 0.5835(13) 0.863(2) 0.3646(2) 0.019(2) Uani 1 1 d . U . . .
H7BA H 0.671446 0.960224 0.361796 0.023 Uiso 1 1 calc R U . . .
H7BB H 0.531646 0.924963 0.379497 0.023 Uiso 1 1 calc R U . . .
C8B C 0.4837(12) 0.877(2) 0.3414(2) 0.020(2) Uani 1 1 d . U . . .
H8BA H 0.399908 0.770483 0.344025 0.024 Uiso 1 1 calc R U . . .
H8BB H 0.445127 1.037726 0.339975 0.024 Uiso 1 1 calc R U . . .
C9B C 0.5576(13) 0.812(2) 0.3169(2) 0.025(3) Uani 1 1 d . . . . .
C10B C 0.6628(15) 0.953(2) 0.3067(2) 0.030(3) Uani 1 1 d . . . . .
H10B H 0.688496 1.093630 0.315148 0.036 Uiso 1 1 calc R U . . .
C11B C 0.7331(14) 0.896(3) 0.2845(3) 0.033(3) Uani 1 1 d . . . . .
H11B H 0.805859 0.996307 0.277789 0.040 Uiso 1 1 calc R U . . .
C12B C 0.6964(14) 0.692(2) 0.2721(3) 0.029(3) Uani 1 1 d . . . . .
H12B H 0.743167 0.651122 0.256744 0.035 Uiso 1 1 calc R U . . .
C13B C 0.5933(15) 0.550(2) 0.2820(3) 0.034(3) Uani 1 1 d . . . . .
H13B H 0.570339 0.407481 0.273663 0.041 Uiso 1 1 calc R U . . .
C14B C 0.5182(15) 0.608(2) 0.3045(2) 0.028(3) Uani 1 1 d . . . . .
H14B H 0.443508 0.509461 0.310960 0.033 Uiso 1 1 calc R U . . .
C15B C 0.5109(12) 0.960(2) 0.4853(2) 0.018(2) Uani 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
S1A O2A 1.417(8) . ?
S1A O1A 1.462(8) . ?
S1A N1A 1.610(10) . ?
S1A C4A 1.783(12) . ?
N1A C7A 1.448(15) . ?
N1A H1A 0.8800 . ?
N2A C15A 1.158(16) . ?
C1A C2A 1.397(16) . ?
C1A C6A 1.404(16) . ?
C1A C15A 1.455(16) . ?
C2A C3A 1.395(16) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.435(16) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.367(17) . ?
C5A C6A 1.409(17) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
C7A C8A 1.547(16) . ?
C7A H7AA 0.9900 . ?
C7A H7AB 0.9900 . ?
C8A C9A 1.523(17) . ?
C8A H8AA 0.9900 . ?
C8A H8AB 0.9900 . ?
C9A C10A 1.386(19) . ?
C9A C14A 1.388(19) . ?
C10A C11A 1.398(19) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.38(2) . ?
C11A H11A 0.9500 . ?
C12A C13A 1.42(2) . ?
C12A H12A 0.9500 . ?
C13A C14A 1.423(18) . ?
C13A H13A 0.9500 . ?
C14A H14A 0.9500 . ?
S1B O2B 1.430(8) . ?
S1B O1B 1.444(8) . ?
S1B N1B 1.604(9) . ?
S1B C4B 1.780(11) . ?
N1B C7B 1.493(15) . ?
N1B H1B 0.8800 . ?
N2B C15B 1.154(16) . ?
C1B C2B 1.388(16) . ?
C1B C6B 1.400(16) . ?
C1B C15B 1.442(16) . ?
C2B C3B 1.365(17) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.404(17) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.389(15) . ?
C5B C6B 1.386(16) . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
C7B C8B 1.537(15) . ?
C7B H7BA 0.9900 . ?
C7B H7BB 0.9900 . ?
C8B C9B 1.514(17) . ?
C8B H8BA 0.9900 . ?
C8B H8BB 0.9900 . ?
C9B C10B 1.369(18) . ?
C9B C14B 1.390(18) . ?
C10B C11B 1.387(19) . ?
C10B H10B 0.9500 . ?
C11B C12B 1.383(18) . ?
C11B H11B 0.9500 . ?
C12B C13B 1.354(19) . ?
C12B H12B 0.9500 . ?
C13B C14B 1.422(19) . ?
C13B H13B 0.9500 . ?
C14B H14B 0.9500 . ?

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
O2A S1A O1A 120.7(5) . . ?
O2A S1A N1A 105.9(5) . . ?
O1A S1A N1A 108.3(5) . . ?
O2A S1A C4A 108.4(5) . . ?
O1A S1A C4A 105.7(5) . . ?
N1A S1A C4A 107.4(5) . . ?
C7A N1A S1A 118.3(8) . . ?
C7A N1A H1A 120.9 . . ?
S1A N1A H1A 120.9 . . ?
C2A C1A C6A 121.3(11) . . ?
C2A C1A C15A 120.8(11) . . ?
C6A C1A C15A 117.9(11) . . ?
C3A C2A C1A 120.7(11) . . ?
C3A C2A H2A 119.6 . . ?
C1A C2A H2A 119.6 . . ?
C2A C3A C4A 116.8(11) . . ?
C2A C3A H3A 121.6 . . ?
C4A C3A H3A 121.6 . . ?
C5A C4A C3A 122.9(11) . . ?
C5A C4A S1A 121.3(9) . . ?
C3A C4A S1A 115.7(8) . . ?
C4A C5A C6A 119.5(11) . . ?
C4A C5A H5A 120.2 . . ?
C6A C5A H5A 120.2 . . ?
C1A C6A C5A 118.7(11) . . ?
C1A C6A H6A 120.7 . . ?
C5A C6A H6A 120.7 . . ?
N1A C7A C8A 110.7(10) . . ?
N1A C7A H7AA 109.5 . . ?
C8A C7A H7AA 109.5 . . ?
N1A C7A H7AB 109.5 . . ?
C8A C7A H7AB 109.5 . . ?
H7AA C7A H7AB 108.1 . . ?
C9A C8A C7A 113.2(10) . . ?
C9A C8A H8AA 108.9 . . ?
C7A C8A H8AA 108.9 . . ?
C9A C8A H8AB 108.9 . . ?
C7A C8A H8AB 108.9 . . ?
H8AA C8A H8AB 107.8 . . ?
C10A C9A C14A 120.9(12) . . ?
C10A C9A C8A 122.3(12) . . ?
C14A C9A C8A 116.8(12) . . ?
C9A C10A C11A 119.2(13) . . ?
C9A C10A H10A 120.4 . . ?
C11A C10A H10A 120.4 . . ?
C12A C11A C10A 121.6(14) . . ?
C12A C11A H11A 119.2 . . ?
C10A C11A H11A 119.2 . . ?
C11A C12A C13A 119.5(13) . . ?
C11A C12A H12A 120.2 . . ?
C13A C12A H12A 120.2 . . ?
C12A C13A C14A 118.6(13) . . ?
C12A C13A H13A 120.7 . . ?
C14A C13A H13A 120.7 . . ?
C9A C14A C13A 120.0(13) . . ?
C9A C14A H14A 120.0 . . ?
C13A C14A H14A 120.0 . . ?
N2A C15A C1A 179.0(14) . . ?
O2B S1B O1B 116.9(5) . . ?
O2B S1B N1B 109.0(5) . . ?
O1B S1B N1B 108.1(5) . . ?
O2B S1B C4B 106.9(5) . . ?
O1B S1B C4B 108.8(5) . . ?
N1B S1B C4B 106.7(5) . . ?
C7B N1B S1B 117.6(7) . . ?
C7B N1B H1B 121.2 . . ?
S1B N1B H1B 121.2 . . ?
C2B C1B C6B 120.2(10) . . ?
C2B C1B C15B 120.1(11) . . ?
C6B C1B C15B 119.7(11) . . ?
C3B C2B C1B 121.8(11) . . ?
C3B C2B H2B 119.1 . . ?
C1B C2B H2B 119.1 . . ?
C2B C3B C4B 118.5(11) . . ?
C2B C3B H3B 120.7 . . ?
C4B C3B H3B 120.7 . . ?
C5B C4B C3B 120.0(11) . . ?
C5B C4B S1B 119.4(8) . . ?
C3B C4B S1B 120.6(9) . . ?
C6B C5B C4B 121.4(11) . . ?
C6B C5B H5B 119.3 . . ?
C4B C5B H5B 119.3 . . ?
C5B C6B C1B 118.0(10) . . ?
C5B C6B H6B 121.0 . . ?
C1B C6B H6B 121.0 . . ?
N1B C7B C8B 109.3(9) . . ?
N1B C7B H7BA 109.8 . . ?
C8B C7B H7BA 109.8 . . ?
N1B C7B H7BB 109.8 . . ?
C8B C7B H7BB 109.8 . . ?
H7BA C7B H7BB 108.3 . . ?
C9B C8B C7B 114.3(9) . . ?
C9B C8B H8BA 108.7 . . ?
C7B C8B H8BA 108.7 . . ?
C9B C8B H8BB 108.7 . . ?
C7B C8B H8BB 108.7 . . ?
H8BA C8B H8BB 107.6 . . ?
C10B C9B C14B 119.4(12) . . ?
C10B C9B C8B 120.9(12) . . ?
C14B C9B C8B 119.7(12) . . ?
C9B C10B C11B 121.8(12) . . ?
C9B C10B H10B 119.1 . . ?
C11B C10B H10B 119.1 . . ?
C12B C11B C10B 119.5(12) . . ?
C12B C11B H11B 120.2 . . ?
C10B C11B H11B 120.2 . . ?
C13B C12B C11B 119.4(13) . . ?
C13B C12B H12B 120.3 . . ?
C11B C12B H12B 120.3 . . ?
C12B C13B C14B 121.9(13) . . ?
C12B C13B H13B 119.1 . . ?
C14B C13B H13B 119.1 . . ?
C9B C14B C13B 118.0(12) . . ?
C9B C14B H14B 121.0 . . ?
C13B C14B H14B 121.0 . . ?
N2B C15B C1B 178.3(14) . . ?

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
O2A S1A N1A C7A 174.7(8) . . . . ?
O1A S1A N1A C7A -54.6(9) . . . . ?
C4A S1A N1A C7A 59.1(10) . . . . ?
C6A C1A C2A C3A -1.6(18) . . . . ?
C15A C1A C2A C3A 178.9(11) . . . . ?
C1A C2A C3A C4A 1.5(16) . . . . ?
C2A C3A C4A C5A -1.1(16) . . . . ?
C2A C3A C4A S1A -177.2(9) . . . . ?
O2A S1A C4A C5A 142.3(9) . . . . ?
O1A S1A C4A C5A 11.6(11) . . . . ?
N1A S1A C4A C5A -103.8(10) . . . . ?
O2A S1A C4A C3A -41.6(10) . . . . ?
O1A S1A C4A C3A -172.2(8) . . . . ?
N1A S1A C4A C3A 72.4(9) . . . . ?
C3A C4A C5A C6A 0.6(17) . . . . ?
S1A C4A C5A C6A 176.5(9) . . . . ?
C2A C1A C6A C5A 1.0(17) . . . . ?
C15A C1A C6A C5A -179.5(11) . . . . ?
C4A C5A C6A C1A -0.5(17) . . . . ?
S1A N1A C7A C8A 169.0(8) . . . . ?
N1A C7A C8A C9A -61.0(14) . . . . ?
C7A C8A C9A C10A 107.4(14) . . . . ?
C7A C8A C9A C14A -74.0(15) . . . . ?
C14A C9A C10A C11A 3(2) . . . . ?
C8A C9A C10A C11A -178.6(12) . . . . ?
C9A C10A C11A C12A 0(2) . . . . ?
C10A C11A C12A C13A -2(2) . . . . ?
C11A C12A C13A C14A 1.2(19) . . . . ?
C10A C9A C14A C13A -3.6(19) . . . . ?
C8A C9A C14A C13A 177.8(11) . . . . ?
C12A C13A C14A C9A 1.5(19) . . . . ?
O2B S1B N1B C7B -55.8(9) . . . . ?
O1B S1B N1B C7B 176.1(8) . . . . ?
C4B S1B N1B C7B 59.3(9) . . . . ?
C6B C1B C2B C3B 2.6(17) . . . . ?
C15B C1B C2B C3B -179.1(10) . . . . ?
C1B C2B C3B C4B -2.0(17) . . . . ?
C2B C3B C4B C5B -0.2(16) . . . . ?
C2B C3B C4B S1B 177.6(8) . . . . ?
O2B S1B C4B C5B -169.3(8) . . . . ?
O1B S1B C4B C5B -42.2(10) . . . . ?
N1B S1B C4B C5B 74.2(10) . . . . ?
O2B S1B C4B C3B 12.9(10) . . . . ?
O1B S1B C4B C3B 140.0(9) . . . . ?
N1B S1B C4B C3B -103.6(9) . . . . ?
C3B C4B C5B C6B 1.7(16) . . . . ?
S1B C4B C5B C6B -176.2(9) . . . . ?
C4B C5B C6B C1B -1.0(16) . . . . ?
C2B C1B C6B C5B -1.1(16) . . . . ?
C15B C1B C6B C5B -179.4(10) . . . . ?
S1B N1B C7B C8B 170.5(8) . . . . ?
N1B C7B C8B C9B -66.0(13) . . . . ?
C7B C8B C9B C10B -68.5(15) . . . . ?
C7B C8B C9B C14B 111.4(12) . . . . ?
C14B C9B C10B C11B -0.8(19) . . . . ?
C8B C9B C10B C11B 179.2(12) . . . . ?
C9B C10B C11B C12B 0(2) . . . . ?
C10B C11B C12B C13B -1(2) . . . . ?
C11B C12B C13B C14B 2(2) . . . . ?
C10B C9B C14B C13B 1.9(18) . . . . ?
C8B C9B C14B C13B -178.1(11) . . . . ?
C12B C13B C14B C9B -2(2) . . . . ?

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
_geom_hbond_publ_flag
N1A H1A O1A 0.88 2.49 2.992(13) 116.4 3 yes
C5A H5A O2A 0.95 2.52 3.107(15) 120.4 1_565 yes
C7A H7AB O1A 0.99 2.59 3.304(14) 129.1 3_565 yes
N1B H1B O2B 0.88 2.51 2.991(12) 114.8 3_465 yes
C3B H3B O1B 0.95 2.47 3.099(15) 123.9 1_565 yes
C7B H7BB O2B 0.99 2.59 3.295(14) 128.2 3_475 yes

_refine_diff_density_max         0.809
_refine_diff_density_min         -1.645
_refine_diff_density_rms         0.115

####################################################################### 
# 
# 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_3c
_database_code_depnum_ccdc_archive 'CCDC 2337450'
loop_
_audit_author_name
_audit_author_address
'Rajesh Gonnade'
;CSIR NATIONAL CHEMICAL LABORATORY PUNE INDIA
India
;
_audit_update_record             
;
2024-03-02 deposited with the CCDC.	2024-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H13 Cl N2 O2 S'
_chemical_formula_sum            'C13 H13 Cl N2 O2 S'
_chemical_formula_weight         296.76

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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'
H H 0.0000 0.0000 '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                   14.225(3)
_cell_length_b                   7.0381(14)
_cell_length_c                   14.882(3)
_cell_angle_alpha                90
_cell_angle_beta                 116.423(7)
_cell_angle_gamma                90
_cell_volume                     1334.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9907
_cell_measurement_theta_min      3.20
_cell_measurement_theta_max      30.54

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.230
_exptl_absorpt_coefficient_mu    0.441
_shelx_estimated_absorpt_T_min   0.843
_shelx_estimated_absorpt_T_max   0.905
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.7029
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'SADABS,(Bruker, 2006)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_source_type              'Incoatech I\mS HB'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            41523
_diffrn_reflns_av_unetI/netI     0.0097
_diffrn_reflns_av_R_equivalents  0.0196
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.748
_diffrn_reflns_theta_max         30.512
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             4025
_reflns_number_gt                3842
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL, Mercury 2020.20'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0358P)²+0.5479P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'direct method'
_atom_sites_solution_secondary   'difference Fourier'
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4025
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0276
_refine_ls_R_factor_gt           0.0265
_refine_ls_wR_factor_ref         0.0737
_refine_ls_wR_factor_gt          0.0728
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.003
_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
Cl1 Cl 0.63166(2) 0.29078(4) 0.53211(2) 0.02379(7) Uani 1 1 d . . . . .
S1 S 0.27845(2) 0.29593(3) 0.67376(2) 0.01540(6) Uani 1 1 d . . . . .
O1 O 0.23769(6) 0.10519(10) 0.66082(6) 0.02323(15) Uani 1 1 d . . . . .
O2 O 0.31992(6) 0.38385(12) 0.77104(5) 0.02377(15) Uani 1 1 d . . . . .
N1 N 0.18389(6) 0.42437(11) 0.59577(6) 0.01486(14) Uani 1 1 d . . . . .
H1N H 0.1500(12) 0.372(2) 0.5392(11) 0.030(4) Uiso 1 1 d . . . . .
N2 N -0.05543(6) 0.68863(11) 0.60894(6) 0.01593(14) Uani 1 1 d . . . . .
C1 C 0.53454(7) 0.29127(13) 0.57299(7) 0.01678(16) Uani 1 1 d . . . . .
C2 C 0.43842(7) 0.20700(13) 0.51237(7) 0.01772(17) Uani 1 1 d . . . . .
H2 H 0.426126 0.150304 0.450171 0.021 Uiso 1 1 calc R U . . .
C3 C 0.36094(7) 0.20784(13) 0.54506(7) 0.01640(16) Uani 1 1 d . . . . .
H3 H 0.295010 0.149569 0.505614 0.020 Uiso 1 1 calc R U . . .
C4 C 0.38013(7) 0.29452(12) 0.63606(6) 0.01412(15) Uani 1 1 d . . . . .
C5 C 0.47660(7) 0.37878(13) 0.69582(7) 0.01727(16) Uani 1 1 d . . . . .
H5 H 0.488744 0.437308 0.757558 0.021 Uiso 1 1 calc R U . . .
C6 C 0.55520(7) 0.37627(13) 0.66398(7) 0.01857(17) Uani 1 1 d . . . . .
H6 H 0.621772 0.431863 0.703972 0.022 Uiso 1 1 calc R U . . .
C7 C 0.19505(7) 0.63128(13) 0.59156(7) 0.01587(16) Uani 1 1 d . . . . .
H7A H 0.217916 0.663302 0.539540 0.019 Uiso 1 1 calc R U . . .
H7B H 0.249006 0.677975 0.656992 0.019 Uiso 1 1 calc R U . . .
C8 C 0.08988(7) 0.72684(13) 0.56681(6) 0.01523(15) Uani 1 1 d . . . . .
H8A H 0.097211 0.865160 0.559574 0.018 Uiso 1 1 calc R U . . .
H8B H 0.036955 0.678414 0.501304 0.018 Uiso 1 1 calc R U . . .
C9 C 0.04964(7) 0.69553(12) 0.64421(6) 0.01354(15) Uani 1 1 d . . . . .
C10 C 0.11666(7) 0.67953(14) 0.74637(7) 0.01808(17) Uani 1 1 d . . . . .
H10 H 0.190606 0.682600 0.769667 0.022 Uiso 1 1 calc R U . . .
C11 C 0.07421(8) 0.65905(14) 0.81381(7) 0.01942(17) Uani 1 1 d . . . . .
H11 H 0.118869 0.647702 0.883644 0.023 Uiso 1 1 calc R U . . .
C12 C -0.03376(8) 0.65534(13) 0.77824(7) 0.01852(17) Uani 1 1 d . . . . .
H12 H -0.064840 0.643606 0.822774 0.022 Uiso 1 1 calc R U . . .
C13 C -0.09510(7) 0.66932(14) 0.67533(7) 0.01887(17) Uani 1 1 d . . . . .
H13 H -0.169235 0.665007 0.650408 0.023 Uiso 1 1 calc R 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
Cl1 C1 1.7398(10) . ?
S1 O2 1.4377(8) . ?
S1 O1 1.4409(8) . ?
S1 N1 1.6076(8) . ?
S1 C4 1.7689(9) . ?
N1 C7 1.4692(12) . ?
N1 H1N 0.847(16) . ?
N2 C13 1.3451(12) . ?
N2 C9 1.3467(11) . ?
C1 C6 1.3870(13) . ?
C1 C2 1.3919(13) . ?
C2 C3 1.3888(13) . ?
C2 H2 0.9500 . ?
C3 C4 1.3970(12) . ?
C3 H3 0.9500 . ?
C4 C5 1.3927(12) . ?
C5 C6 1.3951(13) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.5283(12) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.5133(12) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.3940(12) . ?
C10 C11 1.3900(13) . ?
C10 H10 0.9500 . ?
C11 C12 1.3843(14) . ?
C11 H11 0.9500 . ?
C12 C13 1.3882(13) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?

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
O2 S1 O1 119.73(5) . . ?
O2 S1 N1 108.75(4) . . ?
O1 S1 N1 105.65(4) . . ?
O2 S1 C4 107.15(4) . . ?
O1 S1 C4 106.84(4) . . ?
N1 S1 C4 108.29(4) . . ?
C7 N1 S1 121.10(6) . . ?
C7 N1 H1N 114.6(11) . . ?
S1 N1 H1N 113.2(11) . . ?
C13 N2 C9 118.23(8) . . ?
C6 C1 C2 122.47(8) . . ?
C6 C1 Cl1 119.08(7) . . ?
C2 C1 Cl1 118.45(7) . . ?
C3 C2 C1 118.36(8) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C2 C3 C4 119.88(8) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 121.13(8) . . ?
C5 C4 S1 120.50(7) . . ?
C3 C4 S1 118.37(7) . . ?
C4 C5 C6 119.25(8) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C1 C6 C5 118.91(8) . . ?
C1 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
N1 C7 C8 109.49(7) . . ?
N1 C7 H7A 109.8 . . ?
C8 C7 H7A 109.8 . . ?
N1 C7 H7B 109.8 . . ?
C8 C7 H7B 109.8 . . ?
H7A C7 H7B 108.2 . . ?
C9 C8 C7 114.44(7) . . ?
C9 C8 H8A 108.7 . . ?
C7 C8 H8A 108.7 . . ?
C9 C8 H8B 108.7 . . ?
C7 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
N2 C9 C10 121.60(8) . . ?
N2 C9 C8 116.03(8) . . ?
C10 C9 C8 122.35(8) . . ?
C11 C10 C9 119.33(9) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C12 C11 C10 119.37(8) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C11 C12 C13 117.80(8) . . ?
C11 C12 H12 121.1 . . ?
C13 C12 H12 121.1 . . ?
N2 C13 C12 123.66(9) . . ?
N2 C13 H13 118.2 . . ?
C12 C13 H13 118.2 . . ?

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
O2 S1 N1 C7 46.95(8) . . . . ?
O1 S1 N1 C7 176.67(7) . . . . ?
C4 S1 N1 C7 -69.16(7) . . . . ?
C6 C1 C2 C3 -0.34(14) . . . . ?
Cl1 C1 C2 C3 -179.89(7) . . . . ?
C1 C2 C3 C4 0.97(13) . . . . ?
C2 C3 C4 C5 -0.81(13) . . . . ?
C2 C3 C4 S1 178.91(7) . . . . ?
O2 S1 C4 C5 -3.17(9) . . . . ?
O1 S1 C4 C5 -132.64(7) . . . . ?
N1 S1 C4 C5 113.98(8) . . . . ?
O2 S1 C4 C3 177.10(7) . . . . ?
O1 S1 C4 C3 47.64(8) . . . . ?
N1 S1 C4 C3 -65.74(8) . . . . ?
C3 C4 C5 C6 0.00(13) . . . . ?
S1 C4 C5 C6 -179.71(7) . . . . ?
C2 C1 C6 C5 -0.46(14) . . . . ?
Cl1 C1 C6 C5 179.08(7) . . . . ?
C4 C5 C6 C1 0.62(13) . . . . ?
S1 N1 C7 C8 -145.35(6) . . . . ?
N1 C7 C8 C9 62.25(9) . . . . ?
C13 N2 C9 C10 1.25(13) . . . . ?
C13 N2 C9 C8 -177.16(8) . . . . ?
C7 C8 C9 N2 -148.05(8) . . . . ?
C7 C8 C9 C10 33.55(12) . . . . ?
N2 C9 C10 C11 -1.06(14) . . . . ?
C8 C9 C10 C11 177.25(8) . . . . ?
C9 C10 C11 C12 -0.14(14) . . . . ?
C10 C11 C12 C13 1.05(14) . . . . ?
C9 N2 C13 C12 -0.26(14) . . . . ?
C11 C12 C13 N2 -0.89(15) . . . . ?

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
_geom_hbond_publ_flag
N1 H1N N2 0.847(16) 2.052(16) 2.8807(12) 165.8(16) 3_566 yes
C12 H12 O1 0.95 2.59 3.4213(13) 146.2 2_556 yes
C8 H8A O1 0.99 2.54 3.2941(13) 133.1 1_565 yes
C7 H7A Cl1 0.99 2.80 3.7152(10) 153.7 3_666 yes
C6 H6 O1 0.95 2.44 3.3522(12) 160.9 2_656 yes
C2 H2 O2 0.95 2.42 3.2803(13) 150.3 4_565 yes

_refine_diff_density_max         0.461
_refine_diff_density_min         -0.337
_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_5c
_database_code_depnum_ccdc_archive 'CCDC 2337452'
loop_
_audit_author_name
_audit_author_address
'Rajesh Gonnade'
;CSIR NATIONAL CHEMICAL LABORATORY PUNE INDIA
India
;
_audit_update_record             
;
2024-03-02 deposited with the CCDC.	2024-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H14 N2 O2 S'
_chemical_formula_sum            'C13 H14 N2 O2 S'
_chemical_formula_weight         262.32

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                   5.4885(3)
_cell_length_b                   9.4202(5)
_cell_length_c                   24.6029(14)
_cell_angle_alpha                90
_cell_angle_beta                 95.597(2)
_cell_angle_gamma                90
_cell_volume                     1265.97(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7257
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      34.14

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_F_000             552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.251
_shelx_estimated_absorpt_T_min   0.928
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7001
_exptl_absorpt_correction_T_max  0.7468
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_source_type              'Incoatech I\mS HB'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            11985
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.316
_diffrn_reflns_theta_max         34.558
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.766
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.766
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.766
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             4127
_reflns_number_gt                3702
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL, Mercury 2020.20'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0451P)²+0.6531P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'direct method'
_atom_sites_solution_secondary   'difference Fourier'
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4127
_refine_ls_number_parameters     167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.0981
_refine_ls_wR_factor_gt          0.0947
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.001
_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
S1 S -0.00757(5) 0.12674(3) 0.38533(2) 0.01281(8) Uani 1 1 d . . . . .
O1 O -0.12836(16) 0.25032(9) 0.40431(4) 0.01999(19) Uani 1 1 d . . . . .
O2 O -0.14973(15) 0.00143(9) 0.37045(4) 0.01744(17) Uani 1 1 d . . . . .
N1 N 0.20438(18) 0.07884(11) 0.43057(4) 0.01545(19) Uani 1 1 d . . . . .
H1N H 0.262(3) -0.008(2) 0.4292(8) 0.031(5) Uiso 1 1 d . . . . .
N2 N 0.62583(18) 0.21361(10) 0.57893(4) 0.01515(19) Uani 1 1 d . . . . .
C1 C 0.3142(2) 0.24723(14) 0.22835(5) 0.0200(2) Uani 1 1 d . . . . .
H1 H 0.377698 0.270440 0.194900 0.024 Uiso 1 1 calc R U . . .
C2 C 0.4245(2) 0.14144(14) 0.26156(5) 0.0200(2) Uani 1 1 d . . . . .
H2 H 0.563269 0.092585 0.250724 0.024 Uiso 1 1 calc R U . . .
C3 C 0.3324(2) 0.10661(13) 0.31079(5) 0.0164(2) Uani 1 1 d . . . . .
H3 H 0.408090 0.034819 0.333713 0.020 Uiso 1 1 calc R U . . .
C4 C 0.12743(19) 0.17888(11) 0.32578(5) 0.01233(19) Uani 1 1 d . . . . .
C5 C 0.0152(2) 0.28470(12) 0.29261(5) 0.0153(2) Uani 1 1 d . . . . .
H5 H -0.125014 0.332730 0.303100 0.018 Uiso 1 1 calc R U . . .
C6 C 0.1108(2) 0.31931(13) 0.24395(5) 0.0191(2) Uani 1 1 d . . . . .
H6 H 0.036999 0.392292 0.221327 0.023 Uiso 1 1 calc R U . . .
C7 C 0.3496(2) 0.18054(12) 0.46538(5) 0.0155(2) Uani 1 1 d . . . . .
H7A H 0.350299 0.273506 0.446629 0.019 Uiso 1 1 calc R U . . .
H7B H 0.520865 0.146688 0.471504 0.019 Uiso 1 1 calc R U . . .
C8 C 0.2458(2) 0.19867(14) 0.52029(5) 0.0184(2) Uani 1 1 d . . . . .
H8A H 0.087188 0.249186 0.514627 0.022 Uiso 1 1 calc R U . . .
H8B H 0.215091 0.103891 0.535614 0.022 Uiso 1 1 calc R U . . .
C9 C 0.4161(2) 0.28029(12) 0.56051(5) 0.0150(2) Uani 1 1 d . . . . .
C10 C 0.3627(2) 0.41689(13) 0.57783(5) 0.0182(2) Uani 1 1 d . . . . .
H10 H 0.214947 0.462308 0.564005 0.022 Uiso 1 1 calc R U . . .
C11 C 0.5271(2) 0.48607(13) 0.61547(5) 0.0200(2) Uani 1 1 d . . . . .
H11 H 0.492521 0.578479 0.628135 0.024 Uiso 1 1 calc R U . . .
C12 C 0.7427(2) 0.41732(13) 0.63413(5) 0.0193(2) Uani 1 1 d . . . . .
H12 H 0.859244 0.461752 0.659746 0.023 Uiso 1 1 calc R U . . .
C13 C 0.7844(2) 0.28245(13) 0.61459(5) 0.0171(2) Uani 1 1 d . . . . .
H13 H 0.933184 0.236242 0.627129 0.021 Uiso 1 1 calc R 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 1.4399(9) . ?
S1 O2 1.4424(9) . ?
S1 N1 1.5948(10) . ?
S1 C4 1.7743(11) . ?
N1 C7 1.4675(15) . ?
N1 H1N 0.877(19) . ?
N2 C13 1.3412(16) . ?
N2 C9 1.3501(15) . ?
C1 C2 1.3897(18) . ?
C1 C6 1.3922(18) . ?
C1 H1 0.9500 . ?
C2 C3 1.3963(17) . ?
C2 H2 0.9500 . ?
C3 C4 1.3949(15) . ?
C3 H3 0.9500 . ?
C4 C5 1.3931(16) . ?
C5 C6 1.3918(16) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.5262(16) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.5046(17) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.3957(16) . ?
C10 C11 1.3905(18) . ?
C10 H10 0.9500 . ?
C11 C12 1.3874(18) . ?
C11 H11 0.9500 . ?
C12 C13 1.3853(16) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?

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 O2 119.29(5) . . ?
O1 S1 N1 109.26(6) . . ?
O2 S1 N1 106.58(5) . . ?
O1 S1 C4 106.65(5) . . ?
O2 S1 C4 106.03(5) . . ?
N1 S1 C4 108.65(5) . . ?
C7 N1 S1 122.71(8) . . ?
C7 N1 H1N 116.9(12) . . ?
S1 N1 H1N 118.6(12) . . ?
C13 N2 C9 118.17(10) . . ?
C2 C1 C6 120.18(11) . . ?
C2 C1 H1 119.9 . . ?
C6 C1 H1 119.9 . . ?
C1 C2 C3 120.30(11) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C2 118.97(11) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C5 C4 C3 121.07(10) . . ?
C5 C4 S1 119.04(8) . . ?
C3 C4 S1 119.71(9) . . ?
C6 C5 C4 119.30(10) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C1 120.17(11) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
N1 C7 C8 111.17(9) . . ?
N1 C7 H7A 109.4 . . ?
C8 C7 H7A 109.4 . . ?
N1 C7 H7B 109.4 . . ?
C8 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C9 C8 C7 112.19(9) . . ?
C9 C8 H8A 109.2 . . ?
C7 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
C7 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
N2 C9 C10 121.61(11) . . ?
N2 C9 C8 115.95(10) . . ?
C10 C9 C8 122.44(11) . . ?
C11 C10 C9 119.56(11) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C12 C11 C10 118.61(11) . . ?
C12 C11 H11 120.7 . . ?
C10 C11 H11 120.7 . . ?
C13 C12 C11 118.52(12) . . ?
C13 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
N2 C13 C12 123.51(11) . . ?
N2 C13 H13 118.2 . . ?
C12 C13 H13 118.2 . . ?

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
O1 S1 N1 C7 -34.54(10) . . . . ?
O2 S1 N1 C7 -164.69(9) . . . . ?
C4 S1 N1 C7 81.45(10) . . . . ?
C6 C1 C2 C3 0.00(19) . . . . ?
C1 C2 C3 C4 0.46(19) . . . . ?
C2 C3 C4 C5 -0.22(18) . . . . ?
C2 C3 C4 S1 174.93(9) . . . . ?
O1 S1 C4 C5 -30.89(11) . . . . ?
O2 S1 C4 C5 97.22(10) . . . . ?
N1 S1 C4 C5 -148.56(9) . . . . ?
O1 S1 C4 C3 153.86(10) . . . . ?
O2 S1 C4 C3 -78.03(10) . . . . ?
N1 S1 C4 C3 36.19(11) . . . . ?
C3 C4 C5 C6 -0.48(17) . . . . ?
S1 C4 C5 C6 -175.66(9) . . . . ?
C4 C5 C6 C1 0.94(18) . . . . ?
C2 C1 C6 C5 -0.71(19) . . . . ?
S1 N1 C7 C8 95.94(11) . . . . ?
N1 C7 C8 C9 169.26(10) . . . . ?
C13 N2 C9 C10 -0.20(17) . . . . ?
C13 N2 C9 C8 179.58(10) . . . . ?
C7 C8 C9 N2 -68.88(14) . . . . ?
C7 C8 C9 C10 110.89(13) . . . . ?
N2 C9 C10 C11 -0.78(17) . . . . ?
C8 C9 C10 C11 179.46(11) . . . . ?
C9 C10 C11 C12 0.98(18) . . . . ?
C10 C11 C12 C13 -0.24(18) . . . . ?
C9 N2 C13 C12 1.00(18) . . . . ?
C11 C12 C13 N2 -0.78(19) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1N N2 0.877(19) 2.05(2) 2.9249(14) 175.3(18) 3_656 yes
C3 H3 O2 0.95 2.53 3.2252(15) 130.6 1_655 yes
C8 H8B O2 0.99 2.57 3.3666(15) 137.2 3_556 yes
C13 H13 O2 0.95 2.53 3.3412(15) 143.1 3_656 yes

_refine_diff_density_max         0.504
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.058

####################################################################### 
# 
# 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_7b
_database_code_depnum_ccdc_archive 'CCDC 2337447'
loop_
_audit_author_name
_audit_author_address
'Rajesh Gonnade'
;CSIR NATIONAL CHEMICAL LABORATORY PUNE INDIA
India
;
_audit_update_record             
;
2024-03-02 deposited with the CCDC.	2024-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H17 N O3 S'
_chemical_formula_sum            'C15 H17 N O3 S'
_chemical_formula_weight         291.35

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'

_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, -z'

_cell_length_a                   7.6373(3)
_cell_length_b                   11.5197(4)
_cell_length_c                   16.1227(6)
_cell_angle_alpha                89.7740(10)
_cell_angle_beta                 80.1100(10)
_cell_angle_gamma                85.6640(10)
_cell_volume                     1393.33(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9779
_cell_measurement_theta_min      3.11
_cell_measurement_theta_max      36.35

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.239
_shelx_estimated_absorpt_T_min   0.958
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.7111
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_process_details   'SADABS,(Bruker, 2006)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_source_type              'Incoatech I\mS HB'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            64204
_diffrn_reflns_av_unetI/netI     0.0117
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.565
_diffrn_reflns_theta_max         29.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             8038
_reflns_number_gt                7689
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0422P)²+0.5734P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'direct method'
_atom_sites_solution_secondary   'difference Fourier'
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8038
_refine_ls_number_parameters     371
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0299
_refine_ls_wR_factor_ref         0.0838
_refine_ls_wR_factor_gt          0.0826
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.002
_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
S1A S 0.07135(3) 0.81115(2) 0.45964(2) 0.01296(6) Uani 1 1 d . . . . .
O1A O -0.10592(9) 0.86921(6) 0.47641(4) 0.01785(13) Uani 1 1 d . . . . .
O2A O 0.09542(9) 0.68839(6) 0.47372(4) 0.01864(13) Uani 1 1 d . . . . .
O3A O 0.36395(9) 0.88249(7) 0.10289(4) 0.02017(14) Uani 1 1 d . . . . .
N1A N 0.18510(10) 0.87526(7) 0.51973(5) 0.01552(14) Uani 1 1 d . . . . .
H1NA H 0.171(2) 0.9482(14) 0.5164(10) 0.030(4) Uiso 1 1 d . . . . .
C1A C 0.29431(11) 0.87321(8) 0.18575(5) 0.01433(15) Uani 1 1 d . . . . .
C2A C 0.35857(12) 0.77583(8) 0.22667(6) 0.01655(16) Uani 1 1 d . . . . .
H2A H 0.448406 0.722642 0.196866 0.020 Uiso 1 1 calc R U . . .
C3A C 0.29133(12) 0.75688(8) 0.31060(5) 0.01506(16) Uani 1 1 d . . . . .
H3A H 0.333524 0.690289 0.338390 0.018 Uiso 1 1 calc R U . . .
C4A C 0.16091(11) 0.83655(7) 0.35403(5) 0.01236(15) Uani 1 1 d . . . . .
C5A C 0.10067(11) 0.93542(7) 0.31420(5) 0.01438(15) Uani 1 1 d . . . . .
H5A H 0.014413 0.990198 0.344716 0.017 Uiso 1 1 calc R U . . .
C6A C 0.16676(12) 0.95394(8) 0.22977(5) 0.01496(16) Uani 1 1 d . . . . .
H6A H 0.125449 1.021032 0.202229 0.018 Uiso 1 1 calc R U . . .
C7A C 0.36767(12) 0.82739(9) 0.52280(6) 0.01776(17) Uani 1 1 d . . . . .
H7A1 H 0.443228 0.833930 0.466835 0.021 Uiso 1 1 calc R U . . .
H7A2 H 0.367210 0.743988 0.537837 0.021 Uiso 1 1 calc R U . . .
C8A C 0.44287(13) 0.89447(9) 0.58815(6) 0.01950(18) Uani 1 1 d . . . . .
H8A1 H 0.568566 0.864907 0.586506 0.023 Uiso 1 1 calc R U . . .
H8A2 H 0.442908 0.977256 0.571426 0.023 Uiso 1 1 calc R U . . .
C9A C 0.34639(12) 0.88868(8) 0.67813(5) 0.01461(15) Uani 1 1 d . . . . .
C10A C 0.24412(12) 0.79730(8) 0.70821(6) 0.01688(16) Uani 1 1 d . . . . .
H10A H 0.227645 0.737260 0.670706 0.020 Uiso 1 1 calc R U . . .
C11A C 0.16581(13) 0.79318(9) 0.79279(6) 0.01897(17) Uani 1 1 d . . . . .
H11A H 0.096540 0.730386 0.812514 0.023 Uiso 1 1 calc R U . . .
C12A C 0.18853(13) 0.88049(9) 0.84846(6) 0.01941(18) Uani 1 1 d . . . . .
H12A H 0.136851 0.876811 0.906287 0.023 Uiso 1 1 calc R U . . .
C13A C 0.28761(13) 0.97334(8) 0.81880(6) 0.01938(17) Uani 1 1 d . . . . .
H13A H 0.302057 1.034035 0.856199 0.023 Uiso 1 1 calc R U . . .
C14A C 0.36543(12) 0.97708(8) 0.73428(6) 0.01731(16) Uani 1 1 d . . . . .
H14A H 0.432586 1.040781 0.714446 0.021 Uiso 1 1 calc R U . . .
C15A C 0.28251(14) 0.97186(9) 0.05688(6) 0.02280(19) Uani 1 1 d . . . . .
H15A H 0.155085 0.961183 0.061649 0.034 Uiso 1 1 calc R U . . .
H15B H 0.338879 0.967290 -0.002516 0.034 Uiso 1 1 calc R U . . .
H15C H 0.297850 1.048244 0.080021 0.034 Uiso 1 1 calc R U . . .
S1B S 0.94178(3) 0.68291(2) 0.05113(2) 0.01335(6) Uani 1 1 d . . . . .
O1B O 0.93522(10) 0.80778(6) 0.04777(4) 0.01884(14) Uani 1 1 d . . . . .
O2B O 1.11338(9) 0.61771(6) 0.03117(4) 0.01803(13) Uani 1 1 d . . . . .
O3B O 0.63641(10) 0.53680(7) 0.39312(4) 0.02444(16) Uani 1 1 d . . . . .
N1B N 0.82407(11) 0.63726(7) -0.01438(5) 0.01558(14) Uani 1 1 d . . . . .
H1NB H 0.844(2) 0.5646(14) -0.0250(9) 0.028(4) Uiso 1 1 d . . . . .
C1B C 0.70466(11) 0.57835(8) 0.31609(5) 0.01598(16) Uani 1 1 d . . . . .
C2B C 0.68687(12) 0.50891(8) 0.24741(6) 0.01683(16) Uani 1 1 d . . . . .
H2B H 0.626007 0.439810 0.256330 0.020 Uiso 1 1 calc R U . . .
C3B C 0.75792(12) 0.54092(8) 0.16656(6) 0.01570(16) Uani 1 1 d . . . . .
H3B H 0.749865 0.492438 0.120040 0.019 Uiso 1 1 calc R U . . .
C4B C 0.84160(11) 0.64483(7) 0.15355(5) 0.01299(15) Uani 1 1 d . . . . .
C5B C 0.85378(11) 0.71634(8) 0.22139(5) 0.01441(15) Uani 1 1 d . . . . .
H5B H 0.907953 0.787894 0.212050 0.017 Uiso 1 1 calc R U . . .
C6B C 0.78630(12) 0.68269(8) 0.30308(5) 0.01617(16) Uani 1 1 d . . . . .
H6B H 0.795892 0.730631 0.349661 0.019 Uiso 1 1 calc R U . . .
C7B C 0.64002(12) 0.68693(8) -0.01157(6) 0.01729(16) Uani 1 1 d . . . . .
H7B1 H 0.639657 0.771656 -0.022125 0.021 Uiso 1 1 calc R U . . .
H7B2 H 0.569349 0.675196 0.044918 0.021 Uiso 1 1 calc R U . . .
C8B C 0.55645(12) 0.62784(9) -0.07829(6) 0.01817(17) Uani 1 1 d . . . . .
H8B1 H 0.545008 0.545063 -0.063121 0.022 Uiso 1 1 calc R U . . .
H8B2 H 0.434866 0.664809 -0.077520 0.022 Uiso 1 1 calc R U . . .
C9B C 0.66028(11) 0.63365(8) -0.16649(5) 0.01382(15) Uani 1 1 d . . . . .
C10B C 0.75008(12) 0.53370(8) -0.20613(6) 0.01779(17) Uani 1 1 d . . . . .
H10B H 0.748084 0.462020 -0.176766 0.021 Uiso 1 1 calc R U . . .
C11B C 0.84274(13) 0.53756(9) -0.28828(6) 0.02165(18) Uani 1 1 d . . . . .
H11B H 0.901134 0.468416 -0.315045 0.026 Uiso 1 1 calc R U . . .
C12B C 0.84987(13) 0.64232(10) -0.33107(6) 0.02263(19) Uani 1 1 d . . . . .
H12B H 0.913927 0.645359 -0.386924 0.027 Uiso 1 1 calc R U . . .
C13B C 0.76250(14) 0.74282(9) -0.29156(6) 0.02113(18) Uani 1 1 d . . . . .
H13B H 0.768333 0.814914 -0.320336 0.025 Uiso 1 1 calc R U . . .
C14B C 0.66672(12) 0.73848(8) -0.21026(6) 0.01725(16) Uani 1 1 d . . . . .
H14C H 0.605245 0.807281 -0.184310 0.021 Uiso 1 1 calc R U . . .
C15B C 0.70545(13) 0.57753(9) 0.46422(6) 0.02118(18) Uani 1 1 d . . . . .
H15D H 0.835710 0.564642 0.453684 0.032 Uiso 1 1 calc R U . . .
H15E H 0.656502 0.534878 0.514564 0.032 Uiso 1 1 calc R U . . .
H15F H 0.671266 0.660883 0.472942 0.032 Uiso 1 1 calc R 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
S1A O2A 1.4344(7) . ?
S1A O1A 1.4464(7) . ?
S1A N1A 1.6220(8) . ?
S1A C4A 1.7547(8) . ?
O3A C1A 1.3574(10) . ?
O3A C15A 1.4328(12) . ?
N1A C7A 1.4690(12) . ?
N1A H1NA 0.842(16) . ?
C1A C6A 1.3959(12) . ?
C1A C2A 1.3988(12) . ?
C2A C3A 1.3850(12) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.3972(11) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.3920(12) . ?
C5A C6A 1.3897(12) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
C7A C8A 1.5227(13) . ?
C7A H7A1 0.9900 . ?
C7A H7A2 0.9900 . ?
C8A C9A 1.5138(12) . ?
C8A H8A1 0.9900 . ?
C8A H8A2 0.9900 . ?
C9A C10A 1.3941(12) . ?
C9A C14A 1.3975(12) . ?
C10A C11A 1.3940(12) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.3908(14) . ?
C11A H11A 0.9500 . ?
C12A C13A 1.3927(14) . ?
C12A H12A 0.9500 . ?
C13A C14A 1.3918(13) . ?
C13A H13A 0.9500 . ?
C14A H14A 0.9500 . ?
C15A H15A 0.9800 . ?
C15A H15B 0.9800 . ?
C15A H15C 0.9800 . ?
S1B O1B 1.4367(7) . ?
S1B O2B 1.4468(7) . ?
S1B N1B 1.6132(8) . ?
S1B C4B 1.7651(9) . ?
O3B C1B 1.3615(10) . ?
O3B C15B 1.4358(12) . ?
N1B C7B 1.4704(12) . ?
N1B H1NB 0.852(15) . ?
C1B C6B 1.3942(12) . ?
C1B C2B 1.3999(13) . ?
C2B C3B 1.3831(12) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.3976(12) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.3918(12) . ?
C5B C6B 1.3942(12) . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
C7B C8B 1.5282(13) . ?
C7B H7B1 0.9900 . ?
C7B H7B2 0.9900 . ?
C8B C9B 1.5083(12) . ?
C8B H8B1 0.9900 . ?
C8B H8B2 0.9900 . ?
C9B C10B 1.3930(12) . ?
C9B C14B 1.3961(12) . ?
C10B C11B 1.3925(13) . ?
C10B H10B 0.9500 . ?
C11B C12B 1.3877(15) . ?
C11B H11B 0.9500 . ?
C12B C13B 1.3909(15) . ?
C12B H12B 0.9500 . ?
C13B C14B 1.3896(13) . ?
C13B H13B 0.9500 . ?
C14B H14C 0.9500 . ?
C15B H15D 0.9800 . ?
C15B H15E 0.9800 . ?
C15B H15F 0.9800 . ?

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
O2A S1A O1A 119.59(4) . . ?
O2A S1A N1A 107.19(4) . . ?
O1A S1A N1A 105.67(4) . . ?
O2A S1A C4A 107.60(4) . . ?
O1A S1A C4A 107.48(4) . . ?
N1A S1A C4A 108.99(4) . . ?
C1A O3A C15A 116.77(7) . . ?
C7A N1A S1A 118.34(6) . . ?
C7A N1A H1NA 115.7(11) . . ?
S1A N1A H1NA 111.5(11) . . ?
O3A C1A C6A 123.78(8) . . ?
O3A C1A C2A 115.84(8) . . ?
C6A C1A C2A 120.38(8) . . ?
C3A C2A C1A 120.06(8) . . ?
C3A C2A H2A 120.0 . . ?
C1A C2A H2A 120.0 . . ?
C2A C3A C4A 119.42(8) . . ?
C2A C3A H3A 120.3 . . ?
C4A C3A H3A 120.3 . . ?
C5A C4A C3A 120.65(8) . . ?
C5A C4A S1A 119.74(6) . . ?
C3A C4A S1A 119.61(6) . . ?
C6A C5A C4A 119.97(8) . . ?
C6A C5A H5A 120.0 . . ?
C4A C5A H5A 120.0 . . ?
C5A C6A C1A 119.48(8) . . ?
C5A C6A H6A 120.3 . . ?
C1A C6A H6A 120.3 . . ?
N1A C7A C8A 109.30(8) . . ?
N1A C7A H7A1 109.8 . . ?
C8A C7A H7A1 109.8 . . ?
N1A C7A H7A2 109.8 . . ?
C8A C7A H7A2 109.8 . . ?
H7A1 C7A H7A2 108.3 . . ?
C9A C8A C7A 116.31(8) . . ?
C9A C8A H8A1 108.2 . . ?
C7A C8A H8A1 108.2 . . ?
C9A C8A H8A2 108.2 . . ?
C7A C8A H8A2 108.2 . . ?
H8A1 C8A H8A2 107.4 . . ?
C10A C9A C14A 118.49(8) . . ?
C10A C9A C8A 123.02(8) . . ?
C14A C9A C8A 118.46(8) . . ?
C11A C10A C9A 120.64(8) . . ?
C11A C10A H10A 119.7 . . ?
C9A C10A H10A 119.7 . . ?
C12A C11A C10A 120.36(9) . . ?
C12A C11A H11A 119.8 . . ?
C10A C11A H11A 119.8 . . ?
C11A C12A C13A 119.50(9) . . ?
C11A C12A H12A 120.3 . . ?
C13A C12A H12A 120.3 . . ?
C14A C13A C12A 119.91(9) . . ?
C14A C13A H13A 120.0 . . ?
C12A C13A H13A 120.0 . . ?
C13A C14A C9A 121.08(9) . . ?
C13A C14A H14A 119.5 . . ?
C9A C14A H14A 119.5 . . ?
O3A C15A H15A 109.5 . . ?
O3A C15A H15B 109.5 . . ?
H15A C15A H15B 109.5 . . ?
O3A C15A H15C 109.5 . . ?
H15A C15A H15C 109.5 . . ?
H15B C15A H15C 109.5 . . ?
O1B S1B O2B 118.58(4) . . ?
O1B S1B N1B 108.58(4) . . ?
O2B S1B N1B 105.62(4) . . ?
O1B S1B C4B 107.47(4) . . ?
O2B S1B C4B 108.14(4) . . ?
N1B S1B C4B 108.07(4) . . ?
C1B O3B C15B 117.29(7) . . ?
C7B N1B S1B 119.76(6) . . ?
C7B N1B H1NB 116.6(10) . . ?
S1B N1B H1NB 113.1(10) . . ?
O3B C1B C6B 124.41(8) . . ?
O3B C1B C2B 115.37(8) . . ?
C6B C1B C2B 120.22(8) . . ?
C3B C2B C1B 119.99(8) . . ?
C3B C2B H2B 120.0 . . ?
C1B C2B H2B 120.0 . . ?
C2B C3B C4B 119.76(8) . . ?
C2B C3B H3B 120.1 . . ?
C4B C3B H3B 120.1 . . ?
C5B C4B C3B 120.44(8) . . ?
C5B C4B S1B 119.48(6) . . ?
C3B C4B S1B 120.01(6) . . ?
C4B C5B C6B 119.84(8) . . ?
C4B C5B H5B 120.1 . . ?
C6B C5B H5B 120.1 . . ?
C5B C6B C1B 119.68(8) . . ?
C5B C6B H6B 120.2 . . ?
C1B C6B H6B 120.2 . . ?
N1B C7B C8B 109.65(7) . . ?
N1B C7B H7B1 109.7 . . ?
C8B C7B H7B1 109.7 . . ?
N1B C7B H7B2 109.7 . . ?
C8B C7B H7B2 109.7 . . ?
H7B1 C7B H7B2 108.2 . . ?
C9B C8B C7B 114.26(7) . . ?
C9B C8B H8B1 108.7 . . ?
C7B C8B H8B1 108.7 . . ?
C9B C8B H8B2 108.7 . . ?
C7B C8B H8B2 108.7 . . ?
H8B1 C8B H8B2 107.6 . . ?
C10B C9B C14B 118.76(8) . . ?
C10B C9B C8B 120.35(8) . . ?
C14B C9B C8B 120.89(8) . . ?
C11B C10B C9B 120.81(9) . . ?
C11B C10B H10B 119.6 . . ?
C9B C10B H10B 119.6 . . ?
C12B C11B C10B 120.07(9) . . ?
C12B C11B H11B 120.0 . . ?
C10B C11B H11B 120.0 . . ?
C11B C12B C13B 119.49(9) . . ?
C11B C12B H12B 120.3 . . ?
C13B C12B H12B 120.3 . . ?
C14B C13B C12B 120.44(9) . . ?
C14B C13B H13B 119.8 . . ?
C12B C13B H13B 119.8 . . ?
C13B C14B C9B 120.41(9) . . ?
C13B C14B H14C 119.8 . . ?
C9B C14B H14C 119.8 . . ?
O3B C15B H15D 109.5 . . ?
O3B C15B H15E 109.5 . . ?
H15D C15B H15E 109.5 . . ?
O3B C15B H15F 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 109.5 . . ?

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
O2A S1A N1A C7A 45.51(8) . . . . ?
O1A S1A N1A C7A 174.09(7) . . . . ?
C4A S1A N1A C7A -70.66(8) . . . . ?
C15A O3A C1A C6A -8.78(13) . . . . ?
C15A O3A C1A C2A 171.38(8) . . . . ?
O3A C1A C2A C3A -177.95(8) . . . . ?
C6A C1A C2A C3A 2.20(14) . . . . ?
C1A C2A C3A C4A -0.83(13) . . . . ?
C2A C3A C4A C5A -1.16(13) . . . . ?
C2A C3A C4A S1A 178.45(7) . . . . ?
O2A S1A C4A C5A 156.02(7) . . . . ?
O1A S1A C4A C5A 26.00(8) . . . . ?
N1A S1A C4A C5A -88.06(8) . . . . ?
O2A S1A C4A C3A -23.59(8) . . . . ?
O1A S1A C4A C3A -153.61(7) . . . . ?
N1A S1A C4A C3A 92.33(8) . . . . ?
C3A C4A C5A C6A 1.79(13) . . . . ?
S1A C4A C5A C6A -177.82(7) . . . . ?
C4A C5A C6A C1A -0.42(13) . . . . ?
O3A C1A C6A C5A 178.59(8) . . . . ?
C2A C1A C6A C5A -1.57(13) . . . . ?
S1A N1A C7A C8A -175.31(6) . . . . ?
N1A C7A C8A C9A 62.01(11) . . . . ?
C7A C8A C9A C10A 24.54(13) . . . . ?
C7A C8A C9A C14A -157.60(9) . . . . ?
C14A C9A C10A C11A -1.30(13) . . . . ?
C8A C9A C10A C11A 176.56(9) . . . . ?
C9A C10A C11A C12A 0.07(14) . . . . ?
C10A C11A C12A C13A 1.14(14) . . . . ?
C11A C12A C13A C14A -1.09(14) . . . . ?
C12A C13A C14A C9A -0.16(14) . . . . ?
C10A C9A C14A C13A 1.35(13) . . . . ?
C8A C9A C14A C13A -176.61(8) . . . . ?
O1B S1B N1B C7B -51.47(8) . . . . ?
O2B S1B N1B C7B -179.64(7) . . . . ?
C4B S1B N1B C7B 64.81(8) . . . . ?
C15B O3B C1B C6B -23.10(14) . . . . ?
C15B O3B C1B C2B 157.48(9) . . . . ?
O3B C1B C2B C3B -177.47(8) . . . . ?
C6B C1B C2B C3B 3.09(14) . . . . ?
C1B C2B C3B C4B -2.34(14) . . . . ?
C2B C3B C4B C5B -0.05(13) . . . . ?
C2B C3B C4B S1B 177.02(7) . . . . ?
O1B S1B C4B C5B -31.28(8) . . . . ?
O2B S1B C4B C5B 97.83(8) . . . . ?
N1B S1B C4B C5B -148.28(7) . . . . ?
O1B S1B C4B C3B 151.63(7) . . . . ?
O2B S1B C4B C3B -79.26(8) . . . . ?
N1B S1B C4B C3B 34.63(8) . . . . ?
C3B C4B C5B C6B 1.70(13) . . . . ?
S1B C4B C5B C6B -175.38(7) . . . . ?
C4B C5B C6B C1B -0.95(13) . . . . ?
O3B C1B C6B C5B 179.18(8) . . . . ?
C2B C1B C6B C5B -1.43(14) . . . . ?
S1B N1B C7B C8B -178.86(6) . . . . ?
N1B C7B C8B C9B -55.68(10) . . . . ?
C7B C8B C9B C10B 109.60(10) . . . . ?
C7B C8B C9B C14B -71.13(11) . . . . ?
C14B C9B C10B C11B -0.84(13) . . . . ?
C8B C9B C10B C11B 178.44(8) . . . . ?
C9B C10B C11B C12B 1.45(14) . . . . ?
C10B C11B C12B C13B -0.60(15) . . . . ?
C11B C12B C13B C14B -0.84(15) . . . . ?
C12B C13B C14B C9B 1.45(14) . . . . ?
C10B C9B C14B C13B -0.60(13) . . . . ?
C8B C9B C14B C13B -179.87(8) . . . . ?

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
_geom_hbond_publ_flag
N1A H1NA O1A 0.842(16) 2.123(16) 2.9588(11) 171.6(15) 2_576 yes
C15A H15A O1B 0.98 2.56 3.3946(12) 142.6 1_455 yes
N1B H1NB O2B 0.852(15) 2.101(16) 2.9458(10) 171.3(14) 2_765 yes
C15B H15D O2A 0.98 2.59 3.3552(12) 134.7 1_655 yes
C15B H15E O3B 0.98 2.65 3.5035(12) 145.6 2_666 yes

_refine_diff_density_max         0.463
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.046

####################################################################### 
# 
# 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_6c
_database_code_depnum_ccdc_archive 'CCDC 2337453'
loop_
_audit_author_name
_audit_author_address
'Rajesh Gonnade'
;CSIR NATIONAL CHEMICAL LABORATORY PUNE INDIA
India
;
_audit_update_record             
;
2024-03-02 deposited with the CCDC.	2024-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H16 N2 O2 S'
_chemical_formula_sum            'C14 H16 N2 O2 S'
_chemical_formula_weight         276.35

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   7.7896(10)
_cell_length_b                   15.722(2)
_cell_length_c                   22.587(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2766.2(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9945
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      33.00

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_F_000             1168
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.233
_shelx_estimated_absorpt_T_min   0.917
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6826
_exptl_absorpt_correction_T_max  0.7466
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_source_type              'Incoatech I\mS HB'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            36770
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.591
_diffrn_reflns_theta_max         33.643
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5428
_reflns_number_gt                4697
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL, Mercury 2020.20'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0534P)²+1.6592P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'direct method'
_atom_sites_solution_secondary   'difference Fourier'
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5428
_refine_ls_number_parameters     177
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0597
_refine_ls_wR_factor_ref         0.1382
_refine_ls_wR_factor_gt          0.1328
_refine_ls_goodness_of_fit_ref   1.166
_refine_ls_restrained_S_all      1.166
_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
S1 S 0.20823(4) 0.13906(2) 0.63602(2) 0.01869(9) Uani 1 1 d . . . . .
O1 O 0.03660(15) 0.13547(8) 0.65930(6) 0.0312(3) Uani 1 1 d . . . . .
O2 O 0.27561(17) 0.06730(7) 0.60429(5) 0.0298(3) Uani 1 1 d . . . . .
N1 N 0.33323(15) 0.15712(8) 0.69097(5) 0.0179(2) Uani 1 1 d . . . . .
H1N H 0.302(3) 0.1967(14) 0.7134(9) 0.033(6) Uiso 1 1 d . . . . .
N2 N 0.71117(17) 0.29391(8) 0.72886(6) 0.0238(3) Uani 1 1 d . . . . .
C1 C 0.2296(2) 0.37167(10) 0.51568(6) 0.0249(3) Uani 1 1 d . . . . .
C2 C 0.3104(2) 0.29596(11) 0.49928(6) 0.0261(3) Uani 1 1 d . . . . .
H2 H 0.371317 0.293497 0.462880 0.031 Uiso 1 1 calc R U . . .
C3 C 0.30364(19) 0.22420(10) 0.53504(6) 0.0236(3) Uani 1 1 d . . . . .
H3 H 0.359993 0.173283 0.523419 0.028 Uiso 1 1 calc R U . . .
C4 C 0.21329(17) 0.22783(9) 0.58807(6) 0.0179(2) Uani 1 1 d . . . . .
C5 C 0.12706(18) 0.30198(9) 0.60458(6) 0.0200(3) Uani 1 1 d . . . . .
H5 H 0.062293 0.303500 0.640203 0.024 Uiso 1 1 calc R U . . .
C6 C 0.1365(2) 0.37341(9) 0.56868(6) 0.0236(3) Uani 1 1 d . . . . .
H6 H 0.079089 0.424099 0.580187 0.028 Uiso 1 1 calc R U . . .
C7 C 0.51612(18) 0.13467(9) 0.68962(7) 0.0211(3) Uani 1 1 d . . . . .
H7A H 0.527009 0.075930 0.674293 0.025 Uiso 1 1 calc R U . . .
H7B H 0.559909 0.134723 0.730768 0.025 Uiso 1 1 calc R U . . .
C8 C 0.63067(18) 0.19272(10) 0.65241(7) 0.0226(3) Uani 1 1 d . . . . .
H8A H 0.747412 0.167910 0.651012 0.027 Uiso 1 1 calc R U . . .
H8B H 0.585775 0.193807 0.611407 0.027 Uiso 1 1 calc R U . . .
C9 C 0.64386(17) 0.28281(9) 0.67455(6) 0.0194(2) Uani 1 1 d . . . . .
C10 C 0.5913(2) 0.35163(11) 0.64024(7) 0.0267(3) Uani 1 1 d . . . . .
H10 H 0.544612 0.342360 0.601917 0.032 Uiso 1 1 calc R U . . .
C11 C 0.6071(2) 0.43358(11) 0.66202(8) 0.0330(4) Uani 1 1 d . . . . .
H11 H 0.570480 0.480895 0.639113 0.040 Uiso 1 1 calc R U . . .
C12 C 0.6769(2) 0.44534(11) 0.71754(8) 0.0337(4) Uani 1 1 d . . . . .
H12 H 0.689886 0.500762 0.733685 0.040 Uiso 1 1 calc R U . . .
C13 C 0.7277(2) 0.37368(11) 0.74927(8) 0.0303(3) Uani 1 1 d . . . . .
H13 H 0.776627 0.381684 0.787389 0.036 Uiso 1 1 calc R U . . .
C14 C 0.2398(3) 0.44944(12) 0.47696(8) 0.0387(4) Uani 1 1 d . . . . .
H14A H 0.338672 0.444500 0.450340 0.058 Uiso 1 1 calc R U . . .
H14B H 0.253008 0.500128 0.501799 0.058 Uiso 1 1 calc R U . . .
H14C H 0.134396 0.454332 0.453522 0.058 Uiso 1 1 calc R 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 O2 1.4359(11) . ?
S1 O1 1.4377(12) . ?
S1 N1 1.6029(12) . ?
S1 C4 1.7670(15) . ?
N1 C7 1.4680(18) . ?
N1 H1N 0.84(2) . ?
N2 C13 1.342(2) . ?
N2 C9 1.3455(18) . ?
C1 C2 1.396(2) . ?
C1 C6 1.400(2) . ?
C1 C14 1.506(2) . ?
C2 C3 1.388(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.3905(19) . ?
C3 H3 0.9500 . ?
C4 C5 1.3961(19) . ?
C5 C6 1.387(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.528(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.506(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.392(2) . ?
C10 C11 1.385(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.379(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.393(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

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
O2 S1 O1 119.45(8) . . ?
O2 S1 N1 107.67(7) . . ?
O1 S1 N1 106.77(7) . . ?
O2 S1 C4 107.85(7) . . ?
O1 S1 C4 106.02(7) . . ?
N1 S1 C4 108.73(6) . . ?
C7 N1 S1 122.06(10) . . ?
C7 N1 H1N 118.0(15) . . ?
S1 N1 H1N 115.2(15) . . ?
C13 N2 C9 118.14(13) . . ?
C2 C1 C6 118.49(14) . . ?
C2 C1 C14 120.96(15) . . ?
C6 C1 C14 120.54(15) . . ?
C3 C2 C1 121.41(14) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C2 C3 C4 119.14(14) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C5 120.52(13) . . ?
C3 C4 S1 120.45(11) . . ?
C5 C4 S1 119.02(11) . . ?
C6 C5 C4 119.63(13) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C6 C1 120.75(14) . . ?
C5 C6 H6 119.6 . . ?
C1 C6 H6 119.6 . . ?
N1 C7 C8 115.75(11) . . ?
N1 C7 H7A 108.3 . . ?
C8 C7 H7A 108.3 . . ?
N1 C7 H7B 108.3 . . ?
C8 C7 H7B 108.3 . . ?
H7A C7 H7B 107.4 . . ?
C9 C8 C7 114.77(12) . . ?
C9 C8 H8A 108.6 . . ?
C7 C8 H8A 108.6 . . ?
C9 C8 H8B 108.6 . . ?
C7 C8 H8B 108.6 . . ?
H8A C8 H8B 107.6 . . ?
N2 C9 C10 121.42(14) . . ?
N2 C9 C8 116.84(12) . . ?
C10 C9 C8 121.74(13) . . ?
C11 C10 C9 119.94(15) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C12 C11 C10 118.88(15) . . ?
C12 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?
C11 C12 C13 118.13(16) . . ?
C11 C12 H12 120.9 . . ?
C13 C12 H12 120.9 . . ?
N2 C13 C12 123.49(16) . . ?
N2 C13 H13 118.3 . . ?
C12 C13 H13 118.3 . . ?
C1 C14 H14A 109.5 . . ?
C1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

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
O2 S1 N1 C7 27.67(13) . . . . ?
O1 S1 N1 C7 157.08(11) . . . . ?
C4 S1 N1 C7 -88.94(12) . . . . ?
C6 C1 C2 C3 -1.8(2) . . . . ?
C14 C1 C2 C3 179.17(16) . . . . ?
C1 C2 C3 C4 0.5(2) . . . . ?
C2 C3 C4 C5 1.5(2) . . . . ?
C2 C3 C4 S1 -177.70(11) . . . . ?
O2 S1 C4 C3 -12.00(13) . . . . ?
O1 S1 C4 C3 -141.04(12) . . . . ?
N1 S1 C4 C3 104.48(12) . . . . ?
O2 S1 C4 C5 168.79(11) . . . . ?
O1 S1 C4 C5 39.76(13) . . . . ?
N1 S1 C4 C5 -74.72(12) . . . . ?
C3 C4 C5 C6 -2.2(2) . . . . ?
S1 C4 C5 C6 177.05(11) . . . . ?
C4 C5 C6 C1 0.8(2) . . . . ?
C2 C1 C6 C5 1.1(2) . . . . ?
C14 C1 C6 C5 -179.85(16) . . . . ?
S1 N1 C7 C8 75.12(15) . . . . ?
N1 C7 C8 C9 64.75(16) . . . . ?
C13 N2 C9 C10 -0.4(2) . . . . ?
C13 N2 C9 C8 178.69(14) . . . . ?
C7 C8 C9 N2 61.58(17) . . . . ?
C7 C8 C9 C10 -119.30(15) . . . . ?
N2 C9 C10 C11 -0.3(2) . . . . ?
C8 C9 C10 C11 -179.39(14) . . . . ?
C9 C10 C11 C12 0.7(3) . . . . ?
C10 C11 C12 C13 -0.3(3) . . . . ?
C9 N2 C13 C12 0.8(3) . . . . ?
C11 C12 C13 N2 -0.5(3) . . . . ?

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
_geom_hbond_publ_flag
C7 H7B O1 0.99 2.49 3.416(2) 155.7 8_657 yes
C8 H8A O1 0.99 2.32 3.2914(18) 167.7 1_655 yes
N1 H1N N2 0.84(2) 2.13(2) 2.9679(17) 177(2) 8_557 yes

_refine_diff_density_max         0.502
_refine_diff_density_min         -0.570
_refine_diff_density_rms         0.068

####################################################################### 
# 
# 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_4c
_database_code_depnum_ccdc_archive 'CCDC 2337451'
loop_
_audit_author_name
_audit_author_address
'Rajesh Gonnade'
;CSIR NATIONAL CHEMICAL LABORATORY PUNE INDIA
India
;
_audit_update_record             
;
2024-03-02 deposited with the CCDC.	2024-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H13 Br N2 O2 S'
_chemical_formula_sum            'C13 H13 Br N2 O2 S'
_chemical_formula_weight         341.22

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'
Br Br -0.2901 2.4595 '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'

_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, -z'

_cell_length_a                   5.5952(2)
_cell_length_b                   12.3194(4)
_cell_length_c                   20.3022(7)
_cell_angle_alpha                88.8110(10)
_cell_angle_beta                 85.7720(10)
_cell_angle_gamma                76.8740(10)
_cell_volume                     1359.14(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9854
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      36.03

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.668
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    3.177
_shelx_estimated_absorpt_T_min   0.555
_shelx_estimated_absorpt_T_max   0.883
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6120
_exptl_absorpt_correction_T_max  0.7472
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_source_type              'Incoatech I\mS HB'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            67292
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.638
_diffrn_reflns_theta_max         36.596
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.910
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.910
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             12244
_reflns_number_gt                11050
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL, Mercury 2020.20'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0279P)²+0.5644P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'direct method'
_atom_sites_solution_secondary   'difference Fourier'
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         12244
_refine_ls_number_parameters     351
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0230
_refine_ls_wR_factor_ref         0.0597
_refine_ls_wR_factor_gt          0.0580
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.003
_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
Br1A Br 0.83672(2) 1.14024(2) 0.66156(2) 0.01963(3) Uani 1 1 d . . . . .
S1A S 0.43827(4) 0.72764(2) 0.56128(2) 0.01274(4) Uani 1 1 d . . . . .
O1A O 0.32776(13) 0.68595(6) 0.62002(4) 0.01796(12) Uani 1 1 d . . . . .
O2A O 0.29071(13) 0.76521(6) 0.50668(4) 0.01829(12) Uani 1 1 d . . . . .
N1A N 0.66995(14) 0.63094(7) 0.53753(4) 0.01459(13) Uani 1 1 d . . . . .
H1NA H 0.736(3) 0.5866(14) 0.5681(8) 0.025(4) Uiso 1 1 d . . . . .
N2A N 1.12980(15) 0.52470(7) 0.35895(4) 0.01561(13) Uani 1 1 d . . . . .
C1A C 0.72020(17) 1.01920(8) 0.63047(5) 0.01528(14) Uani 1 1 d . . . . .
C2A C 0.50406(18) 1.04046(8) 0.59811(5) 0.01807(16) Uani 1 1 d . . . . .
H2A H 0.415086 1.114882 0.591719 0.022 Uiso 1 1 calc R U . . .
C3A C 0.41950(17) 0.95120(8) 0.57516(5) 0.01701(15) Uani 1 1 d . . . . .
H3A H 0.272274 0.964156 0.552803 0.020 Uiso 1 1 calc R U . . .
C4A C 0.55277(16) 0.84270(7) 0.58528(4) 0.01297(13) Uani 1 1 d . . . . .
C5A C 0.77027(17) 0.82258(8) 0.61714(5) 0.01574(14) Uani 1 1 d . . . . .
H5A H 0.860767 0.748280 0.623038 0.019 Uiso 1 1 calc R U . . .
C6A C 0.85513(17) 0.91124(8) 0.64035(5) 0.01700(15) Uani 1 1 d . . . . .
H6A H 1.002659 0.898356 0.662571 0.020 Uiso 1 1 calc R U . . .
C7A C 0.81889(16) 0.64222(7) 0.47648(4) 0.01407(14) Uani 1 1 d . . . . .
H7A1 H 0.992959 0.605820 0.482314 0.017 Uiso 1 1 calc R U . . .
H7A2 H 0.809497 0.722236 0.467213 0.017 Uiso 1 1 calc R U . . .
C8A C 0.73166(17) 0.58964(8) 0.41768(5) 0.01672(15) Uani 1 1 d . . . . .
H8A1 H 0.724098 0.511778 0.428705 0.020 Uiso 1 1 calc R U . . .
H8A2 H 0.563974 0.631321 0.408667 0.020 Uiso 1 1 calc R U . . .
C9A C 0.90230(16) 0.59090(8) 0.35697(4) 0.01427(14) Uani 1 1 d . . . . .
C10A C 0.83235(17) 0.65823(8) 0.30243(5) 0.01668(15) Uani 1 1 d . . . . .
H10A H 0.671105 0.704121 0.302194 0.020 Uiso 1 1 calc R U . . .
C11A C 1.00046(18) 0.65764(8) 0.24843(5) 0.01717(15) Uani 1 1 d . . . . .
H11A H 0.955588 0.702507 0.210717 0.021 Uiso 1 1 calc R U . . .
C12A C 1.23516(18) 0.59027(8) 0.25062(5) 0.01742(15) Uani 1 1 d . . . . .
H12A H 1.354609 0.588478 0.214648 0.021 Uiso 1 1 calc R U . . .
C13A C 1.29124(17) 0.52553(8) 0.30666(5) 0.01711(15) Uani 1 1 d . . . . .
H13A H 1.451952 0.479504 0.308076 0.021 Uiso 1 1 calc R U . . .
Br1B Br 0.90756(2) 1.08669(2) 0.18863(2) 0.02494(3) Uani 1 1 d . . . . .
S1B S 0.40166(4) 0.73986(2) 0.05265(2) 0.01572(4) Uani 1 1 d . . . . .
O1B O 0.25244(16) 0.69845(7) 0.10356(4) 0.02410(15) Uani 1 1 d . . . . .
O2B O 0.29311(14) 0.78899(6) -0.00601(4) 0.01998(13) Uani 1 1 d . . . . .
N1B N 0.62741(17) 0.64032(7) 0.02872(4) 0.01822(14) Uani 1 1 d . . . . .
H1NB H 0.693(3) 0.6510(15) -0.0085(9) 0.032(4) Uiso 1 1 d . . . . .
N2B N 1.15930(15) 0.34049(7) 0.10395(4) 0.01719(14) Uani 1 1 d . . . . .
C1B C 0.75215(18) 0.98571(8) 0.14934(5) 0.01799(16) Uani 1 1 d . . . . .
C2B C 0.7989(2) 0.96616(10) 0.08223(6) 0.0267(2) Uani 1 1 d . . . . .
H2B H 0.905674 1.003258 0.056731 0.032 Uiso 1 1 calc R U . . .
C3B C 0.6878(2) 0.89169(10) 0.05266(5) 0.0255(2) Uani 1 1 d . . . . .
H3B H 0.718721 0.876976 0.006700 0.031 Uiso 1 1 calc R U . . .
C4B C 0.53092(17) 0.83877(8) 0.09076(4) 0.01506(14) Uani 1 1 d . . . . .
C5B C 0.4839(2) 0.85954(10) 0.15798(5) 0.02290(19) Uani 1 1 d . . . . .
H5B H 0.375611 0.823300 0.183526 0.027 Uiso 1 1 calc R U . . .
C6B C 0.5964(2) 0.93379(10) 0.18771(5) 0.0246(2) Uani 1 1 d . . . . .
H6B H 0.566517 0.948533 0.233686 0.030 Uiso 1 1 calc R U . . .
C7B C 0.7828(2) 0.57534(8) 0.07736(5) 0.01933(17) Uani 1 1 d . . . . .
H7B1 H 0.734202 0.609072 0.121560 0.023 Uiso 1 1 calc R U . . .
H7B2 H 0.956502 0.577950 0.065914 0.023 Uiso 1 1 calc R U . . .
C8B C 0.76041(18) 0.45485(8) 0.07972(5) 0.01828(16) Uani 1 1 d . . . . .
H8B1 H 0.588613 0.451605 0.093374 0.022 Uiso 1 1 calc R U . . .
H8B2 H 0.802225 0.421659 0.035182 0.022 Uiso 1 1 calc R U . . .
C9B C 0.93029(17) 0.38934(7) 0.12768(5) 0.01572(15) Uani 1 1 d . . . . .
C10B C 0.85669(18) 0.38480(8) 0.19439(5) 0.01824(16) Uani 1 1 d . . . . .
H10B H 0.693331 0.419368 0.209916 0.022 Uiso 1 1 calc R U . . .
C11B C 1.02232(19) 0.32972(9) 0.23817(5) 0.01915(16) Uani 1 1 d . . . . .
H11B H 0.974936 0.326770 0.283964 0.023 Uiso 1 1 calc R U . . .
C12B C 1.25890(18) 0.27890(8) 0.21382(5) 0.01835(16) Uani 1 1 d . . . . .
H12B H 1.376969 0.240416 0.242471 0.022 Uiso 1 1 calc R U . . .
C13B C 1.31832(18) 0.28586(8) 0.14642(5) 0.01804(16) Uani 1 1 d . . . . .
H13B H 1.479305 0.250240 0.129542 0.022 Uiso 1 1 calc R 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
Br1A C1A 1.8943(9) . ?
S1A O2A 1.4370(7) . ?
S1A O1A 1.4416(7) . ?
S1A N1A 1.6007(8) . ?
S1A C4A 1.7732(9) . ?
N1A C7A 1.4641(12) . ?
N1A H1NA 0.864(17) . ?
N2A C13A 1.3437(12) . ?
N2A C9A 1.3497(12) . ?
C1A C2A 1.3888(13) . ?
C1A C6A 1.3907(13) . ?
C2A C3A 1.3929(13) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.3941(13) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.3904(12) . ?
C5A C6A 1.3894(13) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
C7A C8A 1.5311(13) . ?
C7A H7A1 0.9900 . ?
C7A H7A2 0.9900 . ?
C8A C9A 1.5044(13) . ?
C8A H8A1 0.9900 . ?
C8A H8A2 0.9900 . ?
C9A C10A 1.3949(13) . ?
C10A C11A 1.3900(13) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.3883(14) . ?
C11A H11A 0.9500 . ?
C12A C13A 1.3893(13) . ?
C12A H12A 0.9500 . ?
C13A H13A 0.9500 . ?
Br1B C1B 1.8907(9) . ?
S1B O2B 1.4364(8) . ?
S1B O1B 1.4387(8) . ?
S1B N1B 1.6019(9) . ?
S1B C4B 1.7687(9) . ?
N1B C7B 1.4663(13) . ?
N1B H1NB 0.836(18) . ?
N2B C13B 1.3435(12) . ?
N2B C9B 1.3442(12) . ?
C1B C6B 1.3811(15) . ?
C1B C2B 1.3839(15) . ?
C2B C3B 1.3875(15) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.3903(13) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.3885(13) . ?
C5B C6B 1.3920(15) . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
C7B C8B 1.5172(13) . ?
C7B H7B1 0.9900 . ?
C7B H7B2 0.9900 . ?
C8B C9B 1.5028(13) . ?
C8B H8B1 0.9900 . ?
C8B H8B2 0.9900 . ?
C9B C10B 1.3899(14) . ?
C10B C11B 1.3858(14) . ?
C10B H10B 0.9500 . ?
C11B C12B 1.3887(14) . ?
C11B H11B 0.9500 . ?
C12B C13B 1.3898(14) . ?
C12B H12B 0.9500 . ?
C13B H13B 0.9500 . ?

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
O2A S1A O1A 119.39(5) . . ?
O2A S1A N1A 109.85(4) . . ?
O1A S1A N1A 106.02(4) . . ?
O2A S1A C4A 106.45(4) . . ?
O1A S1A C4A 107.13(4) . . ?
N1A S1A C4A 107.46(4) . . ?
C7A N1A S1A 121.06(6) . . ?
C7A N1A H1NA 118.8(11) . . ?
S1A N1A H1NA 115.9(11) . . ?
C13A N2A C9A 118.15(8) . . ?
C2A C1A C6A 121.82(8) . . ?
C2A C1A Br1A 119.31(7) . . ?
C6A C1A Br1A 118.87(7) . . ?
C1A C2A C3A 119.11(9) . . ?
C1A C2A H2A 120.4 . . ?
C3A C2A H2A 120.4 . . ?
C2A C3A C4A 119.43(9) . . ?
C2A C3A H3A 120.3 . . ?
C4A C3A H3A 120.3 . . ?
C5A C4A C3A 120.90(8) . . ?
C5A C4A S1A 118.86(7) . . ?
C3A C4A S1A 120.17(7) . . ?
C6A C5A C4A 119.94(8) . . ?
C6A C5A H5A 120.0 . . ?
C4A C5A H5A 120.0 . . ?
C5A C6A C1A 118.80(9) . . ?
C5A C6A H6A 120.6 . . ?
C1A C6A H6A 120.6 . . ?
N1A C7A C8A 111.72(7) . . ?
N1A C7A H7A1 109.3 . . ?
C8A C7A H7A1 109.3 . . ?
N1A C7A H7A2 109.3 . . ?
C8A C7A H7A2 109.3 . . ?
H7A1 C7A H7A2 107.9 . . ?
C9A C8A C7A 111.11(7) . . ?
C9A C8A H8A1 109.4 . . ?
C7A C8A H8A1 109.4 . . ?
C9A C8A H8A2 109.4 . . ?
C7A C8A H8A2 109.4 . . ?
H8A1 C8A H8A2 108.0 . . ?
N2A C9A C10A 121.81(8) . . ?
N2A C9A C8A 115.96(8) . . ?
C10A C9A C8A 122.21(8) . . ?
C11A C10A C9A 119.47(9) . . ?
C11A C10A H10A 120.3 . . ?
C9A C10A H10A 120.3 . . ?
C12A C11A C10A 118.77(9) . . ?
C12A C11A H11A 120.6 . . ?
C10A C11A H11A 120.6 . . ?
C11A C12A C13A 118.44(8) . . ?
C11A C12A H12A 120.8 . . ?
C13A C12A H12A 120.8 . . ?
N2A C13A C12A 123.36(9) . . ?
N2A C13A H13A 118.3 . . ?
C12A C13A H13A 118.3 . . ?
O2B S1B O1B 119.71(5) . . ?
O2B S1B N1B 106.48(5) . . ?
O1B S1B N1B 108.73(5) . . ?
O2B S1B C4B 108.60(4) . . ?
O1B S1B C4B 106.33(5) . . ?
N1B S1B C4B 106.28(5) . . ?
C7B N1B S1B 119.94(7) . . ?
C7B N1B H1NB 118.1(12) . . ?
S1B N1B H1NB 113.8(12) . . ?
C13B N2B C9B 118.37(8) . . ?
C6B C1B C2B 121.85(9) . . ?
C6B C1B Br1B 119.76(8) . . ?
C2B C1B Br1B 118.38(8) . . ?
C1B C2B C3B 119.16(10) . . ?
C1B C2B H2B 120.4 . . ?
C3B C2B H2B 120.4 . . ?
C2B C3B C4B 119.54(9) . . ?
C2B C3B H3B 120.2 . . ?
C4B C3B H3B 120.2 . . ?
C5B C4B C3B 120.85(9) . . ?
C5B C4B S1B 120.41(7) . . ?
C3B C4B S1B 118.69(7) . . ?
C4B C5B C6B 119.61(9) . . ?
C4B C5B H5B 120.2 . . ?
C6B C5B H5B 120.2 . . ?
C1B C6B C5B 118.99(9) . . ?
C1B C6B H6B 120.5 . . ?
C5B C6B H6B 120.5 . . ?
N1B C7B C8B 111.60(8) . . ?
N1B C7B H7B1 109.3 . . ?
C8B C7B H7B1 109.3 . . ?
N1B C7B H7B2 109.3 . . ?
C8B C7B H7B2 109.3 . . ?
H7B1 C7B H7B2 108.0 . . ?
C9B C8B C7B 110.31(8) . . ?
C9B C8B H8B1 109.6 . . ?
C7B C8B H8B1 109.6 . . ?
C9B C8B H8B2 109.6 . . ?
C7B C8B H8B2 109.6 . . ?
H8B1 C8B H8B2 108.1 . . ?
N2B C9B C10B 121.65(9) . . ?
N2B C9B C8B 117.22(9) . . ?
C10B C9B C8B 121.05(9) . . ?
C11B C10B C9B 119.80(9) . . ?
C11B C10B H10B 120.1 . . ?
C9B C10B H10B 120.1 . . ?
C10B C11B C12B 118.72(9) . . ?
C10B C11B H11B 120.6 . . ?
C12B C11B H11B 120.6 . . ?
C11B C12B C13B 118.22(9) . . ?
C11B C12B H12B 120.9 . . ?
C13B C12B H12B 120.9 . . ?
N2B C13B C12B 123.23(9) . . ?
N2B C13B H13B 118.4 . . ?
C12B C13B H13B 118.4 . . ?

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
O2A S1A N1A C7A 46.22(8) . . . . ?
O1A S1A N1A C7A 176.50(7) . . . . ?
C4A S1A N1A C7A -69.19(8) . . . . ?
C6A C1A C2A C3A 0.27(15) . . . . ?
Br1A C1A C2A C3A 179.81(7) . . . . ?
C1A C2A C3A C4A 0.19(14) . . . . ?
C2A C3A C4A C5A -0.87(14) . . . . ?
C2A C3A C4A S1A 175.90(7) . . . . ?
O2A S1A C4A C5A -154.60(7) . . . . ?
O1A S1A C4A C5A 76.61(8) . . . . ?
N1A S1A C4A C5A -36.95(8) . . . . ?
O2A S1A C4A C3A 28.57(9) . . . . ?
O1A S1A C4A C3A -100.22(8) . . . . ?
N1A S1A C4A C3A 146.21(7) . . . . ?
C3A C4A C5A C6A 1.09(14) . . . . ?
S1A C4A C5A C6A -175.72(7) . . . . ?
C4A C5A C6A C1A -0.62(14) . . . . ?
C2A C1A C6A C5A -0.05(14) . . . . ?
Br1A C1A C6A C5A -179.59(7) . . . . ?
S1A N1A C7A C8A -93.74(9) . . . . ?
N1A C7A C8A C9A -173.93(8) . . . . ?
C13A N2A C9A C10A 0.53(13) . . . . ?
C13A N2A C9A C8A -178.03(8) . . . . ?
C7A C8A C9A N2A 67.71(11) . . . . ?
C7A C8A C9A C10A -110.84(10) . . . . ?
N2A C9A C10A C11A -0.01(14) . . . . ?
C8A C9A C10A C11A 178.46(9) . . . . ?
C9A C10A C11A C12A -0.51(14) . . . . ?
C10A C11A C12A C13A 0.50(14) . . . . ?
C9A N2A C13A C12A -0.54(14) . . . . ?
C11A C12A C13A N2A 0.02(15) . . . . ?
O2B S1B N1B C7B 177.93(7) . . . . ?
O1B S1B N1B C7B -51.83(9) . . . . ?
C4B S1B N1B C7B 62.27(8) . . . . ?
C6B C1B C2B C3B -0.50(19) . . . . ?
Br1B C1B C2B C3B 179.54(10) . . . . ?
C1B C2B C3B C4B 0.4(2) . . . . ?
C2B C3B C4B C5B 0.05(18) . . . . ?
C2B C3B C4B S1B -177.39(10) . . . . ?
O2B S1B C4B C5B 131.83(9) . . . . ?
O1B S1B C4B C5B 1.77(10) . . . . ?
N1B S1B C4B C5B -113.96(9) . . . . ?
O2B S1B C4B C3B -50.72(10) . . . . ?
O1B S1B C4B C3B 179.22(9) . . . . ?
N1B S1B C4B C3B 63.49(10) . . . . ?
C3B C4B C5B C6B -0.40(18) . . . . ?
S1B C4B C5B C6B 177.00(9) . . . . ?
C2B C1B C6B C5B 0.16(18) . . . . ?
Br1B C1B C6B C5B -179.89(9) . . . . ?
C4B C5B C6B C1B 0.29(18) . . . . ?
S1B N1B C7B C8B 114.88(9) . . . . ?
N1B C7B C8B C9B 177.41(9) . . . . ?
C13B N2B C9B C10B 0.29(14) . . . . ?
C13B N2B C9B C8B 176.91(8) . . . . ?
C7B C8B C9B N2B -89.80(11) . . . . ?
C7B C8B C9B C10B 86.83(11) . . . . ?
N2B C9B C10B C11B 0.61(14) . . . . ?
C8B C9B C10B C11B -175.87(9) . . . . ?
C9B C10B C11B C12B -0.76(15) . . . . ?
C10B C11B C12B C13B 0.03(15) . . . . ?
C9B N2B C13B C12B -1.07(15) . . . . ?
C11B C12B C13B N2B 0.91(15) . . . . ?

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
_geom_hbond_publ_flag
N1A H1NA N2A 0.864(17) 2.062(17) 2.9246(12) 175.8(15) 2_766 yes
C5A H5A O1A 0.95 2.55 3.1945(12) 125.6 1_655 yes
C6A H6A Br1B 0.95 3.11 3.8102(10) 131.4 2_776 yes
C12A H12A O1B 0.95 2.64 3.2482(12) 122.4 1_655 yes
C13A H13A O1A 0.95 2.61 3.3664(12) 137.0 2_766 yes
N1B H1NB N2B 0.836(18) 2.061(18) 2.8918(12) 172.7(17) 2_765 yes
C7B H7B2 O1B 0.99 2.62 3.3967(12) 135.1 1_655 yes
C13B H13B Br1B 0.95 3.06 3.7789(10) 133.5 1_645 yes

_refine_diff_density_max         0.631
_refine_diff_density_min         -0.490
_refine_diff_density_rms         0.062

####################################################################### 
# 
# 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_1c
_database_code_depnum_ccdc_archive 'CCDC 2337448'
loop_
_audit_author_name
_audit_author_address
'Rajesh Gonnade'
;CSIR NATIONAL CHEMICAL LABORATORY PUNE INDIA
India
;
_audit_update_record             
;
2024-03-02 deposited with the CCDC.	2024-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H13 F3 N2 O2 S'
_chemical_formula_sum            'C14 H13 F3 N2 O2 S'
_chemical_formula_weight         330.32

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'
F F 0.0171 0.0103 '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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   25.3896(8)
_cell_length_b                   5.0011(2)
_cell_length_c                   22.3676(8)
_cell_angle_alpha                90
_cell_angle_beta                 94.337(2)
_cell_angle_gamma                90
_cell_volume                     2832.01(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9875
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      37.72

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_F_000             1360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.271
_shelx_estimated_absorpt_T_min   0.916
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.6462
_exptl_absorpt_correction_T_max  0.7474
_exptl_absorpt_process_details   'SADABS,(Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_source_type              'Incoatech I\mS HB'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            21863
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.219
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3414
_reflns_number_gt                3197
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL, Mercury 2020.20'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0307P)²+7.2994P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'direct method'
_atom_sites_solution_secondary   'difference Fourier'
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3414
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.1066
_refine_ls_wR_factor_gt          0.1049
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_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
S1 S 0.36007(2) 0.35476(8) 0.43472(2) 0.01860(12) Uani 1 1 d . . . . .
H1N H 0.2913(10) 0.583(5) 0.4339(11) 0.035(7) Uiso 1 1 d . . . . .
F1 F 0.50878(6) 1.2877(3) 0.31547(7) 0.0523(4) Uani 1 1 d . . . . .
F2 F 0.55462(5) 1.2219(3) 0.39693(6) 0.0449(4) Uani 1 1 d . . . . .
F3 F 0.56023(6) 0.9542(3) 0.32279(8) 0.0573(5) Uani 1 1 d . . . . .
O1 O 0.38601(5) 0.2024(3) 0.48271(6) 0.0242(3) Uani 1 1 d . . . . .
O2 O 0.33773(5) 0.2241(3) 0.38152(6) 0.0263(3) Uani 1 1 d . . . . .
N1 N 0.31321(5) 0.5208(3) 0.46098(7) 0.0189(3) Uani 1 1 d . . . . .
N2 N 0.26740(6) 0.8215(3) 0.63094(6) 0.0205(3) Uani 1 1 d . . . . .
C1 C 0.48401(7) 0.9250(4) 0.37447(8) 0.0196(3) Uani 1 1 d . . . . .
C2 C 0.49005(7) 0.8145(4) 0.43143(8) 0.0206(3) Uani 1 1 d . . . . .
H2 H 0.520267 0.855661 0.457464 0.025 Uiso 1 1 calc R U . . .
C3 C 0.45155(7) 0.6432(4) 0.45003(8) 0.0202(3) Uani 1 1 d . . . . .
H3 H 0.455144 0.567033 0.489034 0.024 Uiso 1 1 calc R U . . .
C4 C 0.40789(6) 0.5838(3) 0.41154(7) 0.0174(3) Uani 1 1 d . . . . .
C5 C 0.40128(7) 0.6991(4) 0.35501(8) 0.0220(4) Uani 1 1 d . . . . .
H5 H 0.370617 0.661151 0.329408 0.026 Uiso 1 1 calc R U . . .
C6 C 0.43958(7) 0.8697(4) 0.33619(8) 0.0235(4) Uani 1 1 d . . . . .
H6 H 0.435598 0.948363 0.297454 0.028 Uiso 1 1 calc R U . . .
C7 C 0.32043(6) 0.6545(3) 0.51929(7) 0.0179(3) Uani 1 1 d . . . . .
H7A H 0.299817 0.822688 0.517935 0.022 Uiso 1 1 calc R U . . .
H7B H 0.358172 0.700988 0.527681 0.022 Uiso 1 1 calc R U . . .
C8 C 0.30272(7) 0.4773(4) 0.56980(8) 0.0217(3) Uani 1 1 d . . . . .
H8A H 0.266434 0.411841 0.559089 0.026 Uiso 1 1 calc R U . . .
H8B H 0.326362 0.320209 0.574774 0.026 Uiso 1 1 calc R U . . .
C9 C 0.30384(7) 0.6294(4) 0.62779(8) 0.0194(3) Uani 1 1 d . . . . .
C10 C 0.34137(7) 0.5806(4) 0.67525(8) 0.0243(4) Uani 1 1 d . . . . .
H10 H 0.367214 0.444937 0.672153 0.029 Uiso 1 1 calc R U . . .
C11 C 0.34056(8) 0.7322(4) 0.72698(8) 0.0276(4) Uani 1 1 d . . . . .
H11 H 0.365720 0.700925 0.759874 0.033 Uiso 1 1 calc R U . . .
C12 C 0.30292(8) 0.9285(4) 0.73022(8) 0.0267(4) Uani 1 1 d . . . . .
H12 H 0.301441 1.034618 0.765281 0.032 Uiso 1 1 calc R U . . .
C13 C 0.26729(7) 0.9673(4) 0.68112(8) 0.0240(4) Uani 1 1 d . . . . .
H13 H 0.241505 1.104003 0.683095 0.029 Uiso 1 1 calc R U . . .
C14 C 0.52696(8) 1.0961(4) 0.35308(8) 0.0263(4) 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
S1 O1 1.4352(13) . ?
S1 O2 1.4360(13) . ?
S1 N1 1.5985(14) . ?
S1 C4 1.7748(17) . ?
F1 C14 1.334(2) . ?
F2 C14 1.322(2) . ?
F3 C14 1.328(2) . ?
N1 C7 1.465(2) . ?
N1 H1N 0.85(3) . ?
N2 C13 1.339(2) . ?
N2 C9 1.339(2) . ?
C1 C2 1.387(2) . ?
C1 C6 1.391(2) . ?
C1 C14 1.493(2) . ?
C2 C3 1.387(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.384(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(2) . ?
C5 C6 1.383(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.530(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.502(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.393(2) . ?
C10 C11 1.385(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.376(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.383(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?

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 O2 120.56(8) . . ?
O1 S1 N1 108.25(8) . . ?
O2 S1 N1 106.40(8) . . ?
O1 S1 C4 106.00(8) . . ?
O2 S1 C4 106.71(8) . . ?
N1 S1 C4 108.47(8) . . ?
C7 N1 S1 121.18(11) . . ?
C7 N1 H1N 119.8(17) . . ?
S1 N1 H1N 113.3(17) . . ?
C13 N2 C9 118.68(16) . . ?
C2 C1 C6 120.95(16) . . ?
C2 C1 C14 119.35(16) . . ?
C6 C1 C14 119.64(16) . . ?
C1 C2 C3 119.36(16) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C4 C3 C2 119.72(16) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 120.89(16) . . ?
C3 C4 S1 119.37(13) . . ?
C5 C4 S1 119.73(13) . . ?
C6 C5 C4 119.61(16) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C6 C1 119.43(16) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
N1 C7 C8 111.66(14) . . ?
N1 C7 H7A 109.3 . . ?
C8 C7 H7A 109.3 . . ?
N1 C7 H7B 109.3 . . ?
C8 C7 H7B 109.3 . . ?
H7A C7 H7B 107.9 . . ?
C9 C8 C7 110.92(14) . . ?
C9 C8 H8A 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 108.0 . . ?
N2 C9 C10 121.39(17) . . ?
N2 C9 C8 116.13(15) . . ?
C10 C9 C8 122.45(16) . . ?
C11 C10 C9 119.23(18) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C12 C11 C10 119.26(17) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C11 C12 C13 118.27(18) . . ?
C11 C12 H12 120.9 . . ?
C13 C12 H12 120.9 . . ?
N2 C13 C12 123.16(18) . . ?
N2 C13 H13 118.4 . . ?
C12 C13 H13 118.4 . . ?
F2 C14 F3 108.07(17) . . ?
F2 C14 F1 105.39(17) . . ?
F3 C14 F1 105.38(17) . . ?
F2 C14 C1 113.26(15) . . ?
F3 C14 C1 111.43(16) . . ?
F1 C14 C1 112.80(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
O1 S1 N1 C7 41.86(15) . . . . ?
O2 S1 N1 C7 172.79(13) . . . . ?
C4 S1 N1 C7 -72.73(15) . . . . ?
C6 C1 C2 C3 1.0(3) . . . . ?
C14 C1 C2 C3 -176.33(16) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
C2 C3 C4 C5 -1.8(3) . . . . ?
C2 C3 C4 S1 177.67(13) . . . . ?
O1 S1 C4 C3 -19.94(16) . . . . ?
O2 S1 C4 C3 -149.61(14) . . . . ?
N1 S1 C4 C3 96.11(15) . . . . ?
O1 S1 C4 C5 159.54(14) . . . . ?
O2 S1 C4 C5 29.87(16) . . . . ?
N1 S1 C4 C5 -84.40(15) . . . . ?
C3 C4 C5 C6 1.9(3) . . . . ?
S1 C4 C5 C6 -177.56(14) . . . . ?
C4 C5 C6 C1 -0.6(3) . . . . ?
C2 C1 C6 C5 -0.9(3) . . . . ?
C14 C1 C6 C5 176.43(16) . . . . ?
S1 N1 C7 C8 -93.46(16) . . . . ?
N1 C7 C8 C9 -172.75(14) . . . . ?
C13 N2 C9 C10 -0.3(2) . . . . ?
C13 N2 C9 C8 -178.57(15) . . . . ?
C7 C8 C9 N2 69.70(19) . . . . ?
C7 C8 C9 C10 -108.51(19) . . . . ?
N2 C9 C10 C11 0.7(3) . . . . ?
C8 C9 C10 C11 178.82(16) . . . . ?
C9 C10 C11 C12 -0.4(3) . . . . ?
C10 C11 C12 C13 -0.3(3) . . . . ?
C9 N2 C13 C12 -0.3(3) . . . . ?
C11 C12 C13 N2 0.7(3) . . . . ?
C2 C1 C14 F2 -28.8(2) . . . . ?
C6 C1 C14 F2 153.83(17) . . . . ?
C2 C1 C14 F3 93.3(2) . . . . ?
C6 C1 C14 F3 -84.1(2) . . . . ?
C2 C1 C14 F1 -148.44(17) . . . . ?
C6 C1 C14 F1 34.2(2) . . . . ?

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
_geom_hbond_publ_flag
N1 H1N N2 0.85(3) 2.05(3) 2.898(2) 171(2) 7_566 yes
C13 H13 O2 0.95 2.54 3.300(2) 137.5 7_566 yes

_refine_diff_density_max         0.861
_refine_diff_density_min         -0.541
_refine_diff_density_rms         0.060

####################################################################### 
# 
# 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_6a
_database_code_depnum_ccdc_archive 'CCDC 2337440'
loop_
_audit_author_name
_audit_author_address
'Rajesh Gonnade'
;CSIR NATIONAL CHEMICAL LABORATORY PUNE INDIA
India
;
_audit_update_record             
;
2024-03-02 deposited with the CCDC.	2024-05-27 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_6a                  
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low . 0.894 Why?
RESPONSE: The reason is attributed to the subpar quality of the single crystals, 
which failed to diffract at high angles.
;
_vrf_PLAT340_6a                  
;
PROBLEM: Low Bond Precision on C-C Bonds ............... 0.01227 Ang.
RESPONSE: The reason is attributed to the subpar quality of the single crystals, 
which failed to diffract at high angles.
;
_vrf_PLAT911_6a                  
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L= 0.600 538 Report
RESPONSE: The insufficient diffraction to high 2theta values may be a result of 
the low quality of the single crystals.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H16 O3 S'
_chemical_formula_sum            'C15 H16 O3 S'
_chemical_formula_weight         276.34

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'
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'

_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, -z'

_cell_length_a                   7.3793(6)
_cell_length_b                   8.1389(7)
_cell_length_c                   24.315(2)
_cell_angle_alpha                85.636(5)
_cell_angle_beta                 89.814(5)
_cell_angle_gamma                74.498(4)
_cell_volume                     1402.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3640
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      25.78

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.232
_shelx_estimated_absorpt_T_min   0.947
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.947
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_process_details   SADABS,(BRUKER,2006)
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_source_type              'Incoatech I\mS HB'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            9648
_diffrn_reflns_av_unetI/netI     0.0734
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         0.840
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.886
_diffrn_measured_fraction_theta_full 0.894
_diffrn_reflns_Laue_measured_fraction_max 0.886
_diffrn_reflns_Laue_measured_fraction_full 0.894
_diffrn_reflns_point_group_measured_fraction_max 0.886
_diffrn_reflns_point_group_measured_fraction_full 0.894
_reflns_number_total             4877
_reflns_number_gt                3911
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL, Mercury 2020.20'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0542P)²+12.2037P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'direct method'
_atom_sites_solution_secondary   'difference Fourier'
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4877
_refine_ls_number_parameters     345
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1373
_refine_ls_R_factor_gt           0.1224
_refine_ls_wR_factor_ref         0.3076
_refine_ls_wR_factor_gt          0.3000
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_restrained_S_all      1.103
_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
S1A S -0.0550(3) 0.9163(3) 0.88550(9) 0.0450(5) Uani 1 1 d . . . . .
O1A O -0.2344(8) 0.9138(8) 0.8641(3) 0.0636(18) Uani 1 1 d . . . . .
O2A O -0.0416(9) 1.0437(8) 0.9207(3) 0.0643(18) Uani 1 1 d . . . . .
O3A O 0.0618(7) 0.9312(7) 0.8323(2) 0.0479(14) Uani 1 1 d . . . . .
C1A C 0.2426(10) 0.3908(11) 0.9616(4) 0.047(2) Uani 1 1 d . . . . .
C2A C 0.1354(13) 0.4136(11) 0.9123(4) 0.054(2) Uani 1 1 d . . . . .
H2A H 0.123960 0.319215 0.894715 0.065 Uiso 1 1 calc R U . . .
C3A C 0.0490(12) 0.5748(11) 0.8905(3) 0.048(2) Uani 1 1 d . . . . .
H3A H -0.018147 0.589977 0.857309 0.058 Uiso 1 1 calc R U . . .
C4A C 0.0598(10) 0.7126(10) 0.9165(3) 0.0364(16) Uani 1 1 d . . . . .
C5A C 0.1549(11) 0.6943(11) 0.9658(3) 0.047(2) Uani 1 1 d . . . . .
H5A H 0.157958 0.789383 0.984304 0.056 Uiso 1 1 calc R U . . .
C6A C 0.2452(12) 0.5332(13) 0.9871(4) 0.056(2) Uani 1 1 d . . . . .
H6A H 0.311159 0.520413 1.020413 0.068 Uiso 1 1 calc R U . . .
C7A C 0.2467(12) 0.9618(11) 0.8390(4) 0.050(2) Uani 1 1 d . . . . .
H7AA H 0.297302 0.919459 0.875655 0.060 Uiso 1 1 calc R U . . .
H7AB H 0.235833 1.083536 0.834311 0.060 Uiso 1 1 calc R U . . .
C8A C 0.3772(12) 0.8693(11) 0.7957(3) 0.050(2) Uani 1 1 d . . . . .
H8AA H 0.317722 0.903464 0.759548 0.060 Uiso 1 1 calc R U . . .
H8AB H 0.492666 0.904736 0.795689 0.060 Uiso 1 1 calc R U . . .
C9A C 0.4250(10) 0.6770(10) 0.8051(3) 0.0406(18) Uani 1 1 d . . . . .
C10A C 0.5379(11) 0.5932(12) 0.8490(3) 0.047(2) Uani 1 1 d . . . . .
H10A H 0.579846 0.656231 0.874062 0.056 Uiso 1 1 calc R U . . .
C11A C 0.5903(11) 0.4159(12) 0.8564(3) 0.051(2) Uani 1 1 d . . . . .
H11A H 0.669005 0.360180 0.885728 0.061 Uiso 1 1 calc R U . . .
C12A C 0.5240(11) 0.3229(12) 0.8195(4) 0.057(2) Uani 1 1 d . . . . .
H12A H 0.557542 0.204066 0.824148 0.068 Uiso 1 1 calc R U . . .
C13A C 0.4107(12) 0.4047(12) 0.7768(4) 0.058(2) Uani 1 1 d . . . . .
H13A H 0.364489 0.341418 0.752776 0.069 Uiso 1 1 calc R U . . .
C14A C 0.3620(10) 0.5819(12) 0.7683(3) 0.048(2) Uani 1 1 d . . . . .
H14A H 0.287563 0.636372 0.737951 0.058 Uiso 1 1 calc R U . . .
C15A C 0.3464(15) 0.2141(13) 0.9848(4) 0.072(3) Uani 1 1 d . . . . .
H15A H 0.269367 0.137364 0.980815 0.107 Uiso 1 1 calc R U . . .
H15B H 0.374749 0.216698 1.023181 0.107 Uiso 1 1 calc R U . . .
H15C H 0.461204 0.175495 0.965216 0.107 Uiso 1 1 calc R U . . .
S1B S 0.4504(3) 0.8629(3) 0.61202(8) 0.0419(5) Uani 1 1 d . . . . .
O1B O 0.4600(10) 1.0071(7) 0.5766(3) 0.0639(17) Uani 1 1 d . . . . .
O2B O 0.2704(8) 0.8505(8) 0.6322(3) 0.0595(17) Uani 1 1 d . . . . .
O3B O 0.5678(8) 0.8523(7) 0.6666(2) 0.0495(14) Uani 1 1 d . . . . .
C1B C 0.7515(11) 0.3720(11) 0.5386(3) 0.046(2) Uani 1 1 d . . . . .
C2B C 0.7499(11) 0.5268(12) 0.5116(3) 0.050(2) Uani 1 1 d . . . . .
H2B H 0.813028 0.529483 0.478549 0.060 Uiso 1 1 calc R U . . .
C3B C 0.6557(11) 0.6796(11) 0.5329(3) 0.048(2) Uani 1 1 d . . . . .
H3B H 0.654503 0.783823 0.514183 0.057 Uiso 1 1 calc R U . . .
C4B C 0.5641(10) 0.6744(10) 0.5823(3) 0.0346(16) Uani 1 1 d . . . . .
C5B C 0.5624(11) 0.5210(11) 0.6098(3) 0.0449(19) Uani 1 1 d . . . . .
H5B H 0.500003 0.519515 0.643038 0.054 Uiso 1 1 calc R U . . .
C6B C 0.6523(12) 0.3706(11) 0.5884(4) 0.053(2) Uani 1 1 d . . . . .
H6B H 0.648235 0.267057 0.606638 0.063 Uiso 1 1 calc R U . . .
C7B C 0.7524(13) 0.8836(11) 0.6614(4) 0.056(2) Uani 1 1 d . . . . .
H7BA H 0.742990 1.003251 0.665291 0.067 Uiso 1 1 calc R U . . .
H7BB H 0.802997 0.855381 0.625381 0.067 Uiso 1 1 calc R U . . .
C8B C 0.8812(13) 0.7715(11) 0.7067(4) 0.059(2) Uani 1 1 d . . . . .
H8BA H 0.994145 0.810179 0.709310 0.071 Uiso 1 1 calc R U . . .
H8BB H 0.817801 0.786811 0.741701 0.071 Uiso 1 1 calc R U . . .
C9B C 0.9375(10) 0.5822(10) 0.6973(3) 0.0403(18) Uani 1 1 d . . . . .
C10B C 0.8789(11) 0.4686(11) 0.7326(3) 0.049(2) Uani 1 1 d . . . . .
H10B H 0.801006 0.507907 0.761664 0.059 Uiso 1 1 calc R U . . .
C11B C 0.9344(13) 0.2970(12) 0.7253(4) 0.058(2) Uani 1 1 d . . . . .
H11B H 0.891122 0.220853 0.748863 0.070 Uiso 1 1 calc R U . . .
C12B C 1.0538(12) 0.2368(12) 0.6834(4) 0.054(2) Uani 1 1 d . . . . .
H12B H 1.093985 0.119734 0.679811 0.065 Uiso 1 1 calc R U . . .
C13B C 1.1143(12) 0.3470(12) 0.6469(4) 0.052(2) Uani 1 1 d . . . . .
H13B H 1.192549 0.306939 0.618032 0.063 Uiso 1 1 calc R U . . .
C14B C 1.0539(11) 0.5233(11) 0.6547(3) 0.0465(19) Uani 1 1 d . . . . .
H14B H 1.093413 0.600738 0.630665 0.056 Uiso 1 1 calc R U . . .
C15B C 0.8571(15) 0.2047(13) 0.5176(5) 0.076(3) Uani 1 1 d . . . . .
H15D H 0.777554 0.128501 0.518687 0.114 Uiso 1 1 calc R U . . .
H15E H 0.966844 0.154790 0.540409 0.114 Uiso 1 1 calc R U . . .
H15F H 0.894246 0.223949 0.480314 0.114 Uiso 1 1 calc R 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
S1A O2A 1.417(6) . ?
S1A O1A 1.430(6) . ?
S1A O3A 1.568(6) . ?
S1A C4A 1.760(8) . ?
O3A C7A 1.463(10) . ?
C1A C6A 1.361(12) . ?
C1A C2A 1.412(12) . ?
C1A C15A 1.504(12) . ?
C2A C3A 1.363(12) . ?
C2A H2A 0.9300 . ?
C3A C4A 1.350(11) . ?
C3A H3A 0.9300 . ?
C4A C5A 1.368(11) . ?
C5A C6A 1.365(12) . ?
C5A H5A 0.9300 . ?
C6A H6A 0.9300 . ?
C7A C8A 1.526(11) . ?
C7A H7AA 0.9700 . ?
C7A H7AB 0.9700 . ?
C8A C9A 1.509(12) . ?
C8A H8AA 0.9700 . ?
C8A H8AB 0.9700 . ?
C9A C10A 1.374(11) . ?
C9A C14A 1.385(11) . ?
C10A C11A 1.388(12) . ?
C10A H10A 0.9300 . ?
C11A C12A 1.386(12) . ?
C11A H11A 0.9300 . ?
C12A C13A 1.349(13) . ?
C12A H12A 0.9300 . ?
C13A C14A 1.389(13) . ?
C13A H13A 0.9300 . ?
C14A H14A 0.9300 . ?
C15A H15A 0.9600 . ?
C15A H15B 0.9600 . ?
C15A H15C 0.9600 . ?
S1B O1B 1.419(6) . ?
S1B O2B 1.440(6) . ?
S1B O3B 1.571(6) . ?
S1B C4B 1.749(8) . ?
O3B C7B 1.454(10) . ?
C1B C2B 1.372(12) . ?
C1B C6B 1.414(12) . ?
C1B C15B 1.502(11) . ?
C2B C3B 1.390(11) . ?
C2B H2B 0.9300 . ?
C3B C4B 1.378(11) . ?
C3B H3B 0.9300 . ?
C4B C5B 1.374(11) . ?
C5B C6B 1.368(11) . ?
C5B H5B 0.9300 . ?
C6B H6B 0.9300 . ?
C7B C8B 1.530(12) . ?
C7B H7BA 0.9700 . ?
C7B H7BB 0.9700 . ?
C8B C9B 1.520(12) . ?
C8B H8BA 0.9700 . ?
C8B H8BB 0.9700 . ?
C9B C10B 1.367(11) . ?
C9B C14B 1.375(11) . ?
C10B C11B 1.372(12) . ?
C10B H10B 0.9300 . ?
C11B C12B 1.376(13) . ?
C11B H11B 0.9300 . ?
C12B C13B 1.372(12) . ?
C12B H12B 0.9300 . ?
C13B C14B 1.411(12) . ?
C13B H13B 0.9300 . ?
C14B H14B 0.9300 . ?
C15B H15D 0.9600 . ?
C15B H15E 0.9600 . ?
C15B H15F 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
O2A S1A O1A 120.0(4) . . ?
O2A S1A O3A 109.7(4) . . ?
O1A S1A O3A 103.3(4) . . ?
O2A S1A C4A 109.8(4) . . ?
O1A S1A C4A 109.5(4) . . ?
O3A S1A C4A 103.3(3) . . ?
C7A O3A S1A 117.7(5) . . ?
C6A C1A C2A 117.5(8) . . ?
C6A C1A C15A 122.2(9) . . ?
C2A C1A C15A 120.3(9) . . ?
C3A C2A C1A 119.7(8) . . ?
C3A C2A H2A 120.2 . . ?
C1A C2A H2A 120.2 . . ?
C4A C3A C2A 120.6(8) . . ?
C4A C3A H3A 119.7 . . ?
C2A C3A H3A 119.7 . . ?
C3A C4A C5A 121.0(8) . . ?
C3A C4A S1A 117.8(6) . . ?
C5A C4A S1A 121.2(6) . . ?
C6A C5A C4A 118.5(8) . . ?
C6A C5A H5A 120.7 . . ?
C4A C5A H5A 120.7 . . ?
C1A C6A C5A 122.6(8) . . ?
C1A C6A H6A 118.7 . . ?
C5A C6A H6A 118.7 . . ?
O3A C7A C8A 108.5(7) . . ?
O3A C7A H7AA 110.0 . . ?
C8A C7A H7AA 110.0 . . ?
O3A C7A H7AB 110.0 . . ?
C8A C7A H7AB 110.0 . . ?
H7AA C7A H7AB 108.4 . . ?
C9A C8A C7A 113.4(7) . . ?
C9A C8A H8AA 108.9 . . ?
C7A C8A H8AA 108.9 . . ?
C9A C8A H8AB 108.9 . . ?
C7A C8A H8AB 108.9 . . ?
H8AA C8A H8AB 107.7 . . ?
C10A C9A C14A 119.0(8) . . ?
C10A C9A C8A 120.7(8) . . ?
C14A C9A C8A 120.3(7) . . ?
C9A C10A C11A 121.0(8) . . ?
C9A C10A H10A 119.5 . . ?
C11A C10A H10A 119.5 . . ?
C12A C11A C10A 119.2(8) . . ?
C12A C11A H11A 120.4 . . ?
C10A C11A H11A 120.4 . . ?
C13A C12A C11A 120.0(9) . . ?
C13A C12A H12A 120.0 . . ?
C11A C12A H12A 120.0 . . ?
C12A C13A C14A 121.1(8) . . ?
C12A C13A H13A 119.5 . . ?
C14A C13A H13A 119.5 . . ?
C9A C14A C13A 119.7(8) . . ?
C9A C14A H14A 120.2 . . ?
C13A C14A H14A 120.2 . . ?
C1A C15A H15A 109.5 . . ?
C1A C15A H15B 109.5 . . ?
H15A C15A H15B 109.5 . . ?
C1A C15A H15C 109.5 . . ?
H15A C15A H15C 109.5 . . ?
H15B C15A H15C 109.5 . . ?
O1B S1B O2B 119.2(4) . . ?
O1B S1B O3B 110.7(4) . . ?
O2B S1B O3B 102.9(4) . . ?
O1B S1B C4B 110.1(4) . . ?
O2B S1B C4B 109.5(4) . . ?
O3B S1B C4B 103.1(3) . . ?
C7B O3B S1B 117.4(5) . . ?
C2B C1B C6B 118.5(7) . . ?
C2B C1B C15B 122.5(8) . . ?
C6B C1B C15B 119.0(9) . . ?
C1B C2B C3B 121.2(8) . . ?
C1B C2B H2B 119.4 . . ?
C3B C2B H2B 119.4 . . ?
C4B C3B C2B 119.0(8) . . ?
C4B C3B H3B 120.5 . . ?
C2B C3B H3B 120.5 . . ?
C5B C4B C3B 120.9(7) . . ?
C5B C4B S1B 118.2(6) . . ?
C3B C4B S1B 120.8(6) . . ?
C6B C5B C4B 120.1(7) . . ?
C6B C5B H5B 120.0 . . ?
C4B C5B H5B 120.0 . . ?
C5B C6B C1B 120.2(8) . . ?
C5B C6B H6B 119.9 . . ?
C1B C6B H6B 119.9 . . ?
O3B C7B C8B 108.1(7) . . ?
O3B C7B H7BA 110.1 . . ?
C8B C7B H7BA 110.1 . . ?
O3B C7B H7BB 110.1 . . ?
C8B C7B H7BB 110.1 . . ?
H7BA C7B H7BB 108.4 . . ?
C9B C8B C7B 113.9(7) . . ?
C9B C8B H8BA 108.8 . . ?
C7B C8B H8BA 108.8 . . ?
C9B C8B H8BB 108.8 . . ?
C7B C8B H8BB 108.8 . . ?
H8BA C8B H8BB 107.7 . . ?
C10B C9B C14B 119.6(8) . . ?
C10B C9B C8B 120.0(8) . . ?
C14B C9B C8B 120.3(8) . . ?
C9B C10B C11B 120.2(8) . . ?
C9B C10B H10B 119.9 . . ?
C11B C10B H10B 119.9 . . ?
C10B C11B C12B 120.5(8) . . ?
C10B C11B H11B 119.8 . . ?
C12B C11B H11B 119.8 . . ?
C13B C12B C11B 120.9(8) . . ?
C13B C12B H12B 119.5 . . ?
C11B C12B H12B 119.5 . . ?
C12B C13B C14B 117.8(8) . . ?
C12B C13B H13B 121.1 . . ?
C14B C13B H13B 121.1 . . ?
C9B C14B C13B 121.0(8) . . ?
C9B C14B H14B 119.5 . . ?
C13B C14B H14B 119.5 . . ?
C1B C15B H15D 109.5 . . ?
C1B C15B H15E 109.5 . . ?
H15D C15B H15E 109.5 . . ?
C1B C15B H15F 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 109.5 . . ?

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
O2A S1A O3A C7A 42.4(6) . . . . ?
O1A S1A O3A C7A 171.4(5) . . . . ?
C4A S1A O3A C7A -74.6(6) . . . . ?
C6A C1A C2A C3A 3.8(12) . . . . ?
C15A C1A C2A C3A -177.1(8) . . . . ?
C1A C2A C3A C4A -2.1(13) . . . . ?
C2A C3A C4A C5A -1.0(12) . . . . ?
C2A C3A C4A S1A 179.7(6) . . . . ?
O2A S1A C4A C3A 175.2(6) . . . . ?
O1A S1A C4A C3A 41.6(7) . . . . ?
O3A S1A C4A C3A -67.9(7) . . . . ?
O2A S1A C4A C5A -4.0(7) . . . . ?
O1A S1A C4A C5A -137.7(7) . . . . ?
O3A S1A C4A C5A 112.9(6) . . . . ?
C3A C4A C5A C6A 2.5(12) . . . . ?
S1A C4A C5A C6A -178.3(6) . . . . ?
C2A C1A C6A C5A -2.4(13) . . . . ?
C15A C1A C6A C5A 178.5(8) . . . . ?
C4A C5A C6A C1A -0.7(13) . . . . ?
S1A O3A C7A C8A 145.9(6) . . . . ?
O3A C7A C8A C9A -68.3(9) . . . . ?
C7A C8A C9A C10A -69.5(10) . . . . ?
C7A C8A C9A C14A 113.3(9) . . . . ?
C14A C9A C10A C11A 0.5(12) . . . . ?
C8A C9A C10A C11A -176.7(7) . . . . ?
C9A C10A C11A C12A -1.4(12) . . . . ?
C10A C11A C12A C13A 0.4(13) . . . . ?
C11A C12A C13A C14A 1.5(14) . . . . ?
C10A C9A C14A C13A 1.3(12) . . . . ?
C8A C9A C14A C13A 178.5(8) . . . . ?
C12A C13A C14A C9A -2.3(13) . . . . ?
O1B S1B O3B C7B -43.7(6) . . . . ?
O2B S1B O3B C7B -172.1(6) . . . . ?
C4B S1B O3B C7B 74.0(6) . . . . ?
C6B C1B C2B C3B 1.0(12) . . . . ?
C15B C1B C2B C3B -178.0(8) . . . . ?
C1B C2B C3B C4B 0.6(12) . . . . ?
C2B C3B C4B C5B -1.1(12) . . . . ?
C2B C3B C4B S1B 177.8(6) . . . . ?
O1B S1B C4B C5B -177.4(6) . . . . ?
O2B S1B C4B C5B -44.5(7) . . . . ?
O3B S1B C4B C5B 64.4(6) . . . . ?
O1B S1B C4B C3B 3.6(8) . . . . ?
O2B S1B C4B C3B 136.6(7) . . . . ?
O3B S1B C4B C3B -114.5(7) . . . . ?
C3B C4B C5B C6B 0.0(12) . . . . ?
S1B C4B C5B C6B -178.9(6) . . . . ?
C4B C5B C6B C1B 1.6(12) . . . . ?
C2B C1B C6B C5B -2.1(12) . . . . ?
C15B C1B C6B C5B 176.9(8) . . . . ?
S1B O3B C7B C8B -146.7(6) . . . . ?
O3B C7B C8B C9B 71.8(10) . . . . ?
C7B C8B C9B C10B -114.5(9) . . . . ?
C7B C8B C9B C14B 68.2(11) . . . . ?
C14B C9B C10B C11B -0.6(12) . . . . ?
C8B C9B C10B C11B -177.9(8) . . . . ?
C9B C10B C11B C12B 1.8(14) . . . . ?
C10B C11B C12B C13B -2.4(14) . . . . ?
C11B C12B C13B C14B 1.6(13) . . . . ?
C10B C9B C14B C13B -0.2(12) . . . . ?
C8B C9B C14B C13B 177.1(7) . . . . ?
C12B C13B C14B C9B -0.3(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
_geom_hbond_publ_flag
C8A H8AB O1A 0.97 2.64 3.434(11) 139.8 1_655 yes

_refine_diff_density_max         0.970
_refine_diff_density_min         -0.520
_refine_diff_density_rms         0.099

####################################################################### 
# 
# 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_2c
_database_code_depnum_ccdc_archive 'CCDC 2337449'
loop_
_audit_author_name
_audit_author_address
'Rajesh Gonnade'
;CSIR NATIONAL CHEMICAL LABORATORY PUNE INDIA
India
;
_audit_update_record             
;
2024-03-02 deposited with the CCDC.	2024-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H13 N3 O2 S'
_chemical_formula_sum            'C14 H13 N3 O2 S'
_chemical_formula_weight         287.33

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                   14.7745(4)
_cell_length_b                   6.9327(2)
_cell_length_c                   14.9312(4)
_cell_angle_alpha                90
_cell_angle_beta                 118.4840(10)
_cell_angle_gamma                90
_cell_volume                     1344.23(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9861
_cell_measurement_theta_min      3.14
_cell_measurement_theta_max      34.53

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.245
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.7050
_exptl_absorpt_correction_T_max  0.7469
_exptl_absorpt_process_details   'SADABS,(Bruker, 2006)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_source_type              'Incoatech I\mS HB'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            17833
_diffrn_reflns_av_unetI/netI     0.0128
_diffrn_reflns_av_R_equivalents  0.0174
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.137
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3230
_reflns_number_gt                3036
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL, Mercury 2020.20'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0353P)²+0.8665P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'direct method'
_atom_sites_solution_secondary   'difference Fourier'
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3230
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_ref         0.0816
_refine_ls_wR_factor_gt          0.0803
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.001
_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
S1 S 0.27547(2) 0.69026(4) 0.68451(2) 0.01350(9) Uani 1 1 d . . . . .
O1 O 0.31953(7) 0.59459(15) 0.78152(6) 0.0203(2) Uani 1 1 d . . . . .
O2 O 0.23742(7) 0.88428(14) 0.67527(7) 0.0208(2) Uani 1 1 d . . . . .
N1 N 0.18176(7) 0.56396(15) 0.60302(8) 0.0137(2) Uani 1 1 d . . . . .
H1N H 0.1460(14) 0.622(3) 0.5444(14) 0.030(5) Uiso 1 1 d . . . . .
N2 N -0.05684(8) 0.30470(15) 0.60256(8) 0.0152(2) Uani 1 1 d . . . . .
N3 N 0.66089(9) 0.7159(2) 0.52737(10) 0.0286(3) Uani 1 1 d . . . . .
C1 C 0.52083(9) 0.70715(18) 0.58479(9) 0.0155(2) Uani 1 1 d . . . . .
C2 C 0.42612(9) 0.79804(19) 0.52527(9) 0.0170(2) Uani 1 1 d . . . . .
H2 H 0.412620 0.861182 0.463663 0.020 Uiso 1 1 calc R U . . .
C3 C 0.35236(9) 0.79462(18) 0.55743(9) 0.0159(2) Uani 1 1 d . . . . .
H3 H 0.288281 0.858219 0.518822 0.019 Uiso 1 1 calc R U . . .
C4 C 0.37270(9) 0.69731(17) 0.64682(9) 0.0130(2) Uani 1 1 d . . . . .
C5 C 0.46674(9) 0.60697(18) 0.70590(9) 0.0160(2) Uani 1 1 d . . . . .
H5 H 0.479574 0.541672 0.766769 0.019 Uiso 1 1 calc R U . . .
C6 C 0.54179(9) 0.61311(19) 0.67506(10) 0.0173(2) Uani 1 1 d . . . . .
H6 H 0.606815 0.553699 0.715184 0.021 Uiso 1 1 calc R U . . .
C7 C 0.19047(9) 0.35311(18) 0.59744(9) 0.0144(2) Uani 1 1 d . . . . .
H7A H 0.242273 0.302654 0.664517 0.017 Uiso 1 1 calc R U . . .
H7B H 0.213155 0.320632 0.546666 0.017 Uiso 1 1 calc R U . . .
C8 C 0.08578(9) 0.26109(18) 0.56676(9) 0.0142(2) Uani 1 1 d . . . . .
H8A H 0.034953 0.314168 0.499936 0.017 Uiso 1 1 calc R U . . .
H8B H 0.090931 0.120642 0.558071 0.017 Uiso 1 1 calc R U . . .
C9 C 0.04611(9) 0.29238(17) 0.64216(9) 0.0127(2) Uani 1 1 d . . . . .
C10 C 0.11138(9) 0.30289(19) 0.74655(9) 0.0171(2) Uani 1 1 d . . . . .
H10 H 0.183897 0.296539 0.772900 0.021 Uiso 1 1 calc R U . . .
C11 C 0.06972(10) 0.32274(19) 0.81199(9) 0.0184(3) Uani 1 1 d . . . . .
H11 H 0.113374 0.330488 0.883521 0.022 Uiso 1 1 calc R U . . .
C12 C -0.03606(10) 0.33112(19) 0.77188(10) 0.0178(2) Uani 1 1 d . . . . .
H12 H -0.066756 0.341864 0.814934 0.021 Uiso 1 1 calc R U . . .
C13 C -0.09578(9) 0.32336(19) 0.66705(10) 0.0180(2) Uani 1 1 d . . . . .
H13 H -0.168431 0.331698 0.639117 0.022 Uiso 1 1 calc R U . . .
C14 C 0.59880(10) 0.71162(19) 0.55235(10) 0.0199(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
S1 O1 1.4361(9) . ?
S1 O2 1.4388(10) . ?
S1 N1 1.5991(10) . ?
S1 C4 1.7758(12) . ?
N1 C7 1.4733(16) . ?
N1 H1N 0.874(19) . ?
N2 C13 1.3429(16) . ?
N2 C9 1.3463(15) . ?
N3 C14 1.1436(18) . ?
C1 C6 1.3926(17) . ?
C1 C2 1.3995(17) . ?
C1 C14 1.4473(17) . ?
C2 C3 1.3850(17) . ?
C2 H2 0.9500 . ?
C3 C4 1.3944(17) . ?
C3 H3 0.9500 . ?
C4 C5 1.3898(16) . ?
C5 C6 1.3894(17) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.5275(16) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.5124(16) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.3897(16) . ?
C10 C11 1.3879(17) . ?
C10 H10 0.9500 . ?
C11 C12 1.3826(18) . ?
C11 H11 0.9500 . ?
C12 C13 1.3835(18) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?

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 O2 119.80(6) . . ?
O1 S1 N1 109.03(6) . . ?
O2 S1 N1 106.38(6) . . ?
O1 S1 C4 106.63(6) . . ?
O2 S1 C4 106.38(6) . . ?
N1 S1 C4 108.16(5) . . ?
C7 N1 S1 121.27(8) . . ?
C7 N1 H1N 115.1(13) . . ?
S1 N1 H1N 113.8(13) . . ?
C13 N2 C9 118.15(11) . . ?
C6 C1 C2 121.26(11) . . ?
C6 C1 C14 119.26(11) . . ?
C2 C1 C14 119.48(12) . . ?
C3 C2 C1 119.07(11) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 119.62(11) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 121.29(11) . . ?
C5 C4 S1 120.09(9) . . ?
C3 C4 S1 118.62(9) . . ?
C6 C5 C4 119.35(11) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C1 119.39(11) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
N1 C7 C8 109.15(10) . . ?
N1 C7 H7A 109.8 . . ?
C8 C7 H7A 109.9 . . ?
N1 C7 H7B 109.9 . . ?
C8 C7 H7B 109.8 . . ?
H7A C7 H7B 108.3 . . ?
C9 C8 C7 114.41(10) . . ?
C9 C8 H8A 108.7 . . ?
C7 C8 H8A 108.7 . . ?
C9 C8 H8B 108.7 . . ?
C7 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
N2 C9 C10 121.57(11) . . ?
N2 C9 C8 116.10(10) . . ?
C10 C9 C8 122.31(10) . . ?
C11 C10 C9 119.43(11) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C12 C11 C10 119.24(12) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C11 C12 C13 117.88(11) . . ?
C11 C12 H12 121.1 . . ?
C13 C12 H12 121.1 . . ?
N2 C13 C12 123.70(11) . . ?
N2 C13 H13 118.1 . . ?
C12 C13 H13 118.1 . . ?
N3 C14 C1 179.48(15) . . ?

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
O1 S1 N1 C7 -44.11(11) . . . . ?
O2 S1 N1 C7 -174.59(9) . . . . ?
C4 S1 N1 C7 71.47(10) . . . . ?
C6 C1 C2 C3 0.31(19) . . . . ?
C14 C1 C2 C3 -179.37(11) . . . . ?
C1 C2 C3 C4 -1.51(19) . . . . ?
C2 C3 C4 C5 1.51(19) . . . . ?
C2 C3 C4 S1 -178.45(9) . . . . ?
O1 S1 C4 C5 4.18(12) . . . . ?
O2 S1 C4 C5 133.11(10) . . . . ?
N1 S1 C4 C5 -112.95(10) . . . . ?
O1 S1 C4 C3 -175.86(10) . . . . ?
O2 S1 C4 C3 -46.93(11) . . . . ?
N1 S1 C4 C3 67.01(11) . . . . ?
C3 C4 C5 C6 -0.26(19) . . . . ?
S1 C4 C5 C6 179.70(10) . . . . ?
C4 C5 C6 C1 -0.95(19) . . . . ?
C2 C1 C6 C5 0.94(19) . . . . ?
C14 C1 C6 C5 -179.38(12) . . . . ?
S1 N1 C7 C8 146.33(8) . . . . ?
N1 C7 C8 C9 -62.64(13) . . . . ?
C13 N2 C9 C10 -1.45(18) . . . . ?
C13 N2 C9 C8 176.92(11) . . . . ?
C7 C8 C9 N2 148.03(11) . . . . ?
C7 C8 C9 C10 -33.61(16) . . . . ?
N2 C9 C10 C11 1.29(19) . . . . ?
C8 C9 C10 C11 -176.98(11) . . . . ?
C9 C10 C11 C12 0.18(19) . . . . ?
C10 C11 C12 C13 -1.38(19) . . . . ?
C9 N2 C13 C12 0.17(19) . . . . ?
C11 C12 C13 N2 1.2(2) . . . . ?

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
_geom_hbond_publ_flag
C7 H7B N3 0.99 2.59 3.5254(17) 157.4 3_666 yes
C8 H8B O2 0.99 2.61 3.3176(16) 128.3 1_545 yes
C12 H12 O2 0.95 2.61 3.4421(16) 146.3 2_546 yes
N1 H1N N2 0.874(19) 2.013(19) 2.8730(14) 167.6(18) 3_566 yes

_refine_diff_density_max         0.406
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.047

