# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

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

data_newad328
_database_code_depnum_ccdc_archive 'CCDC 1961865'
loop_
_audit_author_name
_audit_author_address
'Bipul Sarma'
;Tezpur University
India
;
_audit_update_record             
;
2019-12-11 deposited with the CCDC.	2019-12-12 downloaded from the CCDC.
;
_vrf_RINTA01_newad328            
;
PROBLEM: The value of Rint is greater than 0.25
            Rint given   0.253
RESPONSE: For a good approximation the lower the merging R-values
the better the data. Low Multiplicity of Observations (MoO) data
means the Rint is more reliable, for approximately MoO>6 or 7 the
Rsigma seems to be a better value. Crystals are unstable under
X-ray exposure. Also inclusion of solvents (i.e. water) in the
crystal lattice results a high degree of disorder. We understand
that to obtain data with low Rint-values is to collect data
from a good crystal using a well aligned diffractometer and
good data reduction strategies that includes absorption correction.
We could solve this structure based on lousy data collected even
after multiple attempts. 
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H16 N2 O S'
_chemical_formula_weight         248.34

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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

_cell_length_a                   9.914(3)
_cell_length_b                   12.666(5)
_cell_length_c                   10.006(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1256.5(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    629
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      12.30

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.243
_shelx_estimated_absorpt_T_min   0.928
_shelx_estimated_absorpt_T_max   0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.926
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   SADABS
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36233
_diffrn_reflns_av_unetI/netI     0.1509
_diffrn_reflns_av_R_equivalents  0.2530
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.594
_diffrn_reflns_theta_max         28.922
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3217
_reflns_number_gt                1288
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.896
_reflns_Friedel_fraction_max     0.978
_reflns_Friedel_fraction_full    1.000

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_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)] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_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   0.06(19)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3217
_refine_ls_number_parameters     156
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.2005
_refine_ls_R_factor_gt           0.0627
_refine_ls_wR_factor_ref         0.1233
_refine_ls_wR_factor_gt          0.0970
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.055
_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 0.32620(14) 0.16089(13) 0.5620(2) 0.0661(5) Uani 1 1 d . . . . .
O1 O -0.0538(4) 0.0371(3) 0.5282(4) 0.0626(12) Uani 1 1 d . . . . .
H1 H -0.1213 0.0738 0.5190 0.094 Uiso 1 1 d R U . . .
N1 N 0.2175(5) 0.3455(4) 0.4549(5) 0.0582(15) Uani 1 1 d . . . . .
N2 N 0.1299(5) 0.1876(4) 0.3928(5) 0.0530(13) Uani 1 1 d . . . . .
C4 C -0.0293(7) 0.4472(6) 0.2055(7) 0.069(2) Uani 1 1 d . . . . .
H4 H -0.0640 0.5086 0.1678 0.082 Uiso 1 1 calc R U . . .
C5 C 0.0717(7) 0.4544(5) 0.3010(7) 0.067(2) Uani 1 1 d . . . . .
H5 H 0.1067 0.5193 0.3271 0.080 Uiso 1 1 calc R U . . .
C6 C 0.1189(6) 0.3599(5) 0.3565(7) 0.0513(16) Uani 1 1 d . . . . .
C1 C 0.0650(6) 0.2629(5) 0.3148(6) 0.0531(17) Uani 1 1 d . . . . .
C2 C -0.0345(6) 0.2565(6) 0.2194(7) 0.0632(19) Uani 1 1 d . . . . .
H2 H -0.0699 0.1919 0.1926 0.076 Uiso 1 1 calc R U . . .
C3 C -0.0794(6) 0.3499(6) 0.1655(7) 0.070(2) Uani 1 1 d . . . . .
H3 H -0.1457 0.3478 0.0998 0.084 Uiso 1 1 calc R U . . .
C8 C 0.2345(6) 0.0435(5) 0.5081(6) 0.065(2) Uani 1 1 d . . . . .
H8A H 0.2980 -0.0108 0.4813 0.078 Uiso 1 1 calc R U . . .
H8B H 0.1811 0.0164 0.5816 0.078 Uiso 1 1 calc R U . . .
C9 C 0.1410(5) 0.0712(5) 0.3891(6) 0.0530(16) Uani 1 1 d . . . . .
H21 H 0.1849 0.0499 0.3056 0.064 Uiso 1 1 calc R U . . .
C7 C 0.2208(6) 0.2423(6) 0.4691(7) 0.0546(17) Uani 1 1 d . . . . .
C10 C 0.0044(5) 0.0164(5) 0.3995(6) 0.0514(16) Uani 1 1 d . . . . .
H10 H -0.0554 0.0455 0.3307 0.062 Uiso 1 1 calc R U . . .
C11 C 0.0189(5) -0.1016(5) 0.3759(7) 0.0554(17) Uani 1 1 d . . . . .
H11A H 0.0603 -0.1128 0.2893 0.066 Uiso 1 1 calc R U . . .
H11B H 0.0791 -0.1305 0.4430 0.066 Uiso 1 1 calc R U . . .
C12 C -0.1125(6) -0.1611(5) 0.3807(8) 0.0690(19) Uani 1 1 d . . . . .
H12B H -0.1765 -0.1268 0.3216 0.083 Uiso 1 1 calc R U . . .
H12A H -0.1485 -0.1572 0.4708 0.083 Uiso 1 1 calc R U . . .
C13 C -0.1002(6) -0.2768(5) 0.3407(8) 0.082(2) Uani 1 1 d . . . . .
H13C H -0.0436 -0.3130 0.4036 0.123 Uiso 1 1 calc R U . . .
H13B H -0.0612 -0.2816 0.2530 0.123 Uiso 1 1 calc R U . . .
H13A H -0.1880 -0.3087 0.3401 0.123 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 C7 1.737(7) . ?
S1 C8 1.824(6) . ?
O1 C10 1.435(7) . ?
O1 H1 0.8196 . ?
N1 C7 1.316(7) . ?
N1 C6 1.400(8) . ?
N2 C7 1.370(8) . ?
N2 C1 1.390(7) . ?
N2 C9 1.479(7) . ?
C4 C5 1.387(8) . ?
C4 C3 1.389(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.400(8) . ?
C5 H5 0.9300 . ?
C6 C1 1.403(8) . ?
C1 C2 1.375(8) . ?
C2 C3 1.374(8) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C8 C9 1.548(8) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.526(7) . ?
C9 H21 0.9800 . ?
C10 C11 1.520(8) . ?
C10 H10 0.9800 . ?
C11 C12 1.505(7) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.524(8) . ?
C12 H12B 0.9700 . ?
C12 H12A 0.9700 . ?
C13 H13C 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13A 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
C7 S1 C8 91.5(3) . . ?
C10 O1 H1 109.3 . . ?
C7 N1 C6 102.8(5) . . ?
C7 N2 C1 105.7(5) . . ?
C7 N2 C9 117.9(5) . . ?
C1 N2 C9 134.8(5) . . ?
C5 C4 C3 121.0(7) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 117.3(7) . . ?
C4 C5 H5 121.4 . . ?
C6 C5 H5 121.4 . . ?
C5 C6 C1 120.2(6) . . ?
C5 C6 N1 128.6(6) . . ?
C1 C6 N1 111.2(6) . . ?
C2 C1 N2 132.9(7) . . ?
C2 C1 C6 122.1(7) . . ?
N2 C1 C6 104.9(6) . . ?
C3 C2 C1 117.0(7) . . ?
C3 C2 H2 121.5 . . ?
C1 C2 H2 121.5 . . ?
C2 C3 C4 122.3(7) . . ?
C2 C3 H3 118.8 . . ?
C4 C3 H3 118.8 . . ?
C9 C8 S1 110.0(4) . . ?
C9 C8 H8A 109.7 . . ?
S1 C8 H8A 109.7 . . ?
C9 C8 H8B 109.7 . . ?
S1 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
N2 C9 C10 112.7(5) . . ?
N2 C9 C8 104.5(5) . . ?
C10 C9 C8 112.1(5) . . ?
N2 C9 H21 109.1 . . ?
C10 C9 H21 109.1 . . ?
C8 C9 H21 109.1 . . ?
N1 C7 N2 115.2(6) . . ?
N1 C7 S1 131.5(6) . . ?
N2 C7 S1 113.2(5) . . ?
O1 C10 C11 110.9(5) . . ?
O1 C10 C9 109.5(5) . . ?
C11 C10 C9 110.6(5) . . ?
O1 C10 H10 108.6 . . ?
C11 C10 H10 108.6 . . ?
C9 C10 H10 108.6 . . ?
C12 C11 C10 113.9(5) . . ?
C12 C11 H11A 108.8 . . ?
C10 C11 H11A 108.8 . . ?
C12 C11 H11B 108.8 . . ?
C10 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C11 C12 C13 113.8(5) . . ?
C11 C12 H12B 108.8 . . ?
C13 C12 H12B 108.8 . . ?
C11 C12 H12A 108.8 . . ?
C13 C12 H12A 108.8 . . ?
H12B C12 H12A 107.7 . . ?
C12 C13 H13C 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13C C13 H13B 109.5 . . ?
C12 C13 H13A 109.5 . . ?
H13C C13 H13A 109.5 . . ?
H13B C13 H13A 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
C3 C4 C5 C6 -1.1(9) . . . . ?
C4 C5 C6 C1 0.4(9) . . . . ?
C4 C5 C6 N1 -178.9(6) . . . . ?
C7 N1 C6 C5 179.7(6) . . . . ?
C7 N1 C6 C1 0.3(7) . . . . ?
C7 N2 C1 C2 179.7(6) . . . . ?
C9 N2 C1 C2 14.8(11) . . . . ?
C7 N2 C1 C6 -3.0(6) . . . . ?
C9 N2 C1 C6 -167.9(6) . . . . ?
C5 C6 C1 C2 0.0(9) . . . . ?
N1 C6 C1 C2 179.4(5) . . . . ?
C5 C6 C1 N2 -177.7(5) . . . . ?
N1 C6 C1 N2 1.7(7) . . . . ?
N2 C1 C2 C3 177.3(6) . . . . ?
C6 C1 C2 C3 0.3(9) . . . . ?
C1 C2 C3 C4 -1.0(10) . . . . ?
C5 C4 C3 C2 1.4(10) . . . . ?
C7 S1 C8 C9 13.4(5) . . . . ?
C7 N2 C9 C10 137.0(6) . . . . ?
C1 N2 C9 C10 -59.5(9) . . . . ?
C7 N2 C9 C8 15.0(7) . . . . ?
C1 N2 C9 C8 178.5(6) . . . . ?
S1 C8 C9 N2 -17.4(5) . . . . ?
S1 C8 C9 C10 -139.8(5) . . . . ?
C6 N1 C7 N2 -2.4(7) . . . . ?
C6 N1 C7 S1 174.0(5) . . . . ?
C1 N2 C7 N1 3.5(7) . . . . ?
C9 N2 C7 N1 171.5(5) . . . . ?
C1 N2 C7 S1 -173.5(4) . . . . ?
C9 N2 C7 S1 -5.5(7) . . . . ?
C8 S1 C7 N1 178.6(7) . . . . ?
C8 S1 C7 N2 -5.0(5) . . . . ?
N2 C9 C10 O1 -65.3(6) . . . . ?
C8 C9 C10 O1 52.3(6) . . . . ?
N2 C9 C10 C11 172.1(5) . . . . ?
C8 C9 C10 C11 -70.2(7) . . . . ?
O1 C10 C11 C12 59.8(7) . . . . ?
C9 C10 C11 C12 -178.4(6) . . . . ?
C10 C11 C12 C13 173.0(6) . . . . ?

_refine_diff_density_max         0.171
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.051

####################################################################### 
# 
# 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_SKD_AD_328_1_0m
_database_code_depnum_ccdc_archive 'CCDC 1961866'
loop_
_audit_author_name
_audit_author_address
'Bipul Sarma'
;Tezpur University
India
;
_audit_update_record             
;
2019-10-29 deposited with the CCDC.	2019-12-12 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         ?
_chemical_formula_sum            'C13 H16 N2 O S'
_chemical_formula_weight         248.34

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      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                   6.3476(3)
_cell_length_b                   13.4188(6)
_cell_length_c                   15.2697(7)
_cell_angle_alpha                90
_cell_angle_beta                 96.662(3)
_cell_angle_gamma                90
_cell_volume                     1291.85(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4394
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      20.53

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.236
_shelx_estimated_absorpt_T_min   0.939
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.951
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   SADABS
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32562
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_av_R_equivalents  0.0770
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.026
_diffrn_reflns_theta_max         28.666
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3304
_reflns_number_gt                2238
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_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)+(0.1000P)²+0.4397P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3304
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0794
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_ref         0.1660
_refine_ls_wR_factor_gt          0.1400
_refine_ls_goodness_of_fit_ref   0.909
_refine_ls_restrained_S_all      0.909
_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 -0.01135(9) 0.51788(5) 0.89251(4) 0.0542(2) Uani 1 1 d . . . . .
C2 C 0.0081(3) 0.63349(14) 0.66038(13) 0.0418(4) Uani 1 1 d . . . . .
C3 C -0.1827(3) 0.67028(15) 0.68484(15) 0.0446(5) Uani 1 1 d . . . . .
C1 C 0.0842(4) 0.66014(18) 0.58167(15) 0.0553(6) Uani 1 1 d . . . . .
H1 H 0.2110 0.6349 0.5660 0.066 Uiso 1 1 calc R U . . .
C4 C -0.3035(4) 0.73651(18) 0.62920(19) 0.0640(7) Uani 1 1 d . . . . .
H4 H -0.4313 0.7617 0.6439 0.077 Uiso 1 1 calc R U . . .
C6 C -0.0376(5) 0.7257(2) 0.52823(17) 0.0684(7) Uani 1 1 d . . . . .
H6 H 0.0083 0.7452 0.4751 0.082 Uiso 1 1 calc R U . . .
C5 C -0.2263(5) 0.7635(2) 0.55118(19) 0.0727(8) Uani 1 1 d . . . . .
H5 H -0.3033 0.8082 0.5134 0.087 Uiso 1 1 calc R U . . .
N1 N -0.2142(3) 0.63373(13) 0.76793(12) 0.0457(4) Uani 1 1 d . . . . .
N2 N 0.0922(2) 0.57359(12) 0.72984(10) 0.0386(4) Uani 1 1 d . . . . .
C10 C 0.2867(3) 0.51422(14) 0.73378(14) 0.0401(4) Uani 1 1 d . . . . .
H10 H 0.3865 0.5500 0.7008 0.048 Uiso 1 1 calc R U . . .
C7 C -0.0467(3) 0.57750(14) 0.79114(13) 0.0390(4) Uani 1 1 d . . . . .
C9 C 0.3860(3) 0.50717(16) 0.82972(14) 0.0441(5) Uani 1 1 d . . . . .
H9 H 0.5162 0.4677 0.8313 0.053 Uiso 1 1 calc R U . . .
C11 C 0.2362(4) 0.41404(16) 0.68734(17) 0.0558(6) Uani 1 1 d . . . . .
H11A H 0.1402 0.3772 0.7204 0.067 Uiso 1 1 calc R U . . .
H11B H 0.1622 0.4272 0.6293 0.067 Uiso 1 1 calc R U . . .
C8 C 0.2425(4) 0.45732(18) 0.88950(16) 0.0531(6) Uani 1 1 d . . . . .
H8A H 0.3155 0.4553 0.9489 0.064 Uiso 1 1 calc R U . . .
H8B H 0.2178 0.3890 0.8701 0.064 Uiso 1 1 calc R U . . .
C12 C 0.4238(5) 0.3495(2) 0.6770(2) 0.0866(10) Uani 1 1 d . . . . .
H12A H 0.4973 0.3354 0.7350 0.104 Uiso 1 1 calc R U . . .
H12B H 0.3738 0.2866 0.6511 0.104 Uiso 1 1 calc R U . . .
C13 C 0.5777(6) 0.3939(3) 0.6213(3) 0.1313(18) Uani 1 1 d . . . . .
H13A H 0.5029 0.4176 0.5671 0.197 Uiso 1 1 calc R U . . .
H13B H 0.6788 0.3443 0.6088 0.197 Uiso 1 1 calc R U . . .
H13C H 0.6503 0.4485 0.6523 0.197 Uiso 1 1 calc R U . . .
O1 O 0.4408(2) 0.60251(12) 0.86445(11) 0.0553(4) Uani 1 1 d . . . . .
H1A H 0.5326 0.6270 0.8375 0.083 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 C7 1.734(2) . ?
S1 C8 1.810(2) . ?
C2 N2 1.387(3) . ?
C2 C1 1.393(3) . ?
C2 C3 1.398(3) . ?
C3 C4 1.396(3) . ?
C3 N1 1.396(3) . ?
C1 C6 1.375(4) . ?
C1 H1 0.9300 . ?
C4 C5 1.388(4) . ?
C4 H4 0.9300 . ?
C6 C5 1.383(4) . ?
C6 H6 0.9300 . ?
C5 H5 0.9300 . ?
N1 C7 1.318(3) . ?
N2 C7 1.360(2) . ?
N2 C10 1.465(2) . ?
C10 C9 1.529(3) . ?
C10 C11 1.536(3) . ?
C10 H10 0.9800 . ?
C9 O1 1.413(3) . ?
C9 C8 1.518(3) . ?
C9 H9 0.9800 . ?
C11 C12 1.495(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C12 C13 1.491(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
O1 H1A 0.8200 . ?

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
C7 S1 C8 102.01(10) . . ?
N2 C2 C1 131.9(2) . . ?
N2 C2 C3 105.58(17) . . ?
C1 C2 C3 122.5(2) . . ?
C4 C3 N1 130.6(2) . . ?
C4 C3 C2 119.6(2) . . ?
N1 C3 C2 109.80(18) . . ?
C6 C1 C2 116.7(2) . . ?
C6 C1 H1 121.7 . . ?
C2 C1 H1 121.7 . . ?
C5 C4 C3 117.7(2) . . ?
C5 C4 H4 121.1 . . ?
C3 C4 H4 121.1 . . ?
C1 C6 C5 121.9(3) . . ?
C1 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?
C6 C5 C4 121.6(2) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C7 N1 C3 104.43(16) . . ?
C7 N2 C2 106.34(16) . . ?
C7 N2 C10 127.15(16) . . ?
C2 N2 C10 126.45(16) . . ?
N2 C10 C9 108.95(15) . . ?
N2 C10 C11 109.10(17) . . ?
C9 C10 C11 115.39(18) . . ?
N2 C10 H10 107.7 . . ?
C9 C10 H10 107.7 . . ?
C11 C10 H10 107.7 . . ?
N1 C7 N2 113.86(17) . . ?
N1 C7 S1 121.40(15) . . ?
N2 C7 S1 124.72(15) . . ?
O1 C9 C8 108.19(18) . . ?
O1 C9 C10 111.08(18) . . ?
C8 C9 C10 113.22(17) . . ?
O1 C9 H9 108.1 . . ?
C8 C9 H9 108.1 . . ?
C10 C9 H9 108.1 . . ?
C12 C11 C10 115.4(2) . . ?
C12 C11 H11A 108.4 . . ?
C10 C11 H11A 108.4 . . ?
C12 C11 H11B 108.4 . . ?
C10 C11 H11B 108.4 . . ?
H11A C11 H11B 107.5 . . ?
C9 C8 S1 114.55(15) . . ?
C9 C8 H8A 108.6 . . ?
S1 C8 H8A 108.6 . . ?
C9 C8 H8B 108.6 . . ?
S1 C8 H8B 108.6 . . ?
H8A C8 H8B 107.6 . . ?
C13 C12 C11 114.3(3) . . ?
C13 C12 H12A 108.7 . . ?
C11 C12 H12A 108.7 . . ?
C13 C12 H12B 108.7 . . ?
C11 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C9 O1 H1A 109.5 . . ?

_refine_diff_density_max         0.227
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.043


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ehtylacetate'
####################################################################### 
# 
# 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_hbh17
_database_code_depnum_ccdc_archive 'CCDC 1961867'
loop_
_audit_author_name
_audit_author_address
'Bipul Sarma'
;Tezpur University
India
;
_audit_update_record             
;
2019-10-29 deposited with the CCDC.	2019-12-12 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         ?
_chemical_formula_sum            'C16 H12 Br F N2 O S'
_chemical_formula_weight         379.25

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'
Br Br -0.2901 2.4595 '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'
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'
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                   21.440(8)
_cell_length_b                   6.442(2)
_cell_length_c                   30.004(9)
_cell_angle_alpha                90
_cell_angle_beta                 132.808(18)
_cell_angle_gamma                90
_cell_volume                     3040.2(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5843
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      19.93

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.657
_exptl_crystal_F_000             1520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    2.854
_shelx_estimated_absorpt_T_min   0.628
_shelx_estimated_absorpt_T_max   0.763
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.626
_exptl_absorpt_correction_T_max  0.766
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   SADABS
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            70108
_diffrn_reflns_av_unetI/netI     0.1322
_diffrn_reflns_av_R_equivalents  0.2372
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         1.295
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5363
_reflns_number_gt                3505
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_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)+(0.1619P)²+24.9025P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5363
_refine_ls_number_parameters     405
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1137
_refine_ls_R_factor_gt           0.0663
_refine_ls_wR_factor_ref         0.2386
_refine_ls_wR_factor_gt          0.1844
_refine_ls_goodness_of_fit_ref   0.755
_refine_ls_restrained_S_all      0.755
_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
Br1 Br 0.68160(6) 0.65442(16) 0.29839(4) 0.0588(3) Uani 1 1 d . . . . .
S6 S 0.47225(12) 0.7036(3) 0.02649(8) 0.0354(4) Uani 1 1 d . . . . .
F3 F 0.4438(4) 1.3590(7) 0.1512(2) 0.0622(14) Uani 1 1 d . . . . .
O3 O 0.4035(3) 1.1520(8) -0.0016(2) 0.0350(11) Uani 1 1 d D . . . .
N5 N 0.3466(4) 0.5152(9) 0.0106(3) 0.0355(14) Uani 1 1 d . . . . .
N6 N 0.3829(3) 0.8224(8) 0.0579(2) 0.0266(12) Uani 1 1 d . . . . .
C32 C 0.3183(4) 0.7430(11) 0.0530(3) 0.0298(15) Uani 1 1 d . . . . .
C33 C 0.2795(5) 0.8236(12) 0.0727(3) 0.0380(17) Uani 1 1 d . . . . .
H33 H 0.2935 0.9534 0.0909 0.046 Uiso 1 1 calc R U . . .
C34 C 0.2192(5) 0.6975(14) 0.0631(4) 0.046(2) Uani 1 1 d . . . . .
H34 H 0.1920 0.7434 0.0756 0.056 Uiso 1 1 calc R U . . .
C35 C 0.1978(5) 0.5029(14) 0.0353(4) 0.050(2) Uani 1 1 d . . . . .
H35 H 0.1578 0.4214 0.0305 0.060 Uiso 1 1 calc R U . . .
C36 C 0.2350(5) 0.4306(13) 0.0149(4) 0.0460(19) Uani 1 1 d . . . . .
H36 H 0.2196 0.3027 -0.0045 0.055 Uiso 1 1 calc R U . . .
C37 C 0.2966(5) 0.5532(11) 0.0239(3) 0.0344(16) Uani 1 1 d . . . . .
C38 C 0.3968(4) 0.6783(10) 0.0321(3) 0.0288(15) Uani 1 1 d . . . . .
C39 C 0.5261(5) 0.9383(11) 0.0704(3) 0.0327(15) Uani 1 1 d . . . . .
H39A H 0.5689 0.9022 0.1132 0.039 Uiso 1 1 calc R U . . .
H39B H 0.5551 0.9990 0.0591 0.039 Uiso 1 1 calc R U . . .
C40 C 0.4664(4) 1.0991(10) 0.0613(3) 0.0288(14) Uani 1 1 d . . . . .
H40 H 0.4995 1.2241 0.0841 0.035 Uiso 1 1 calc R U . . .
C41 C 0.4876(4) 1.0203(11) 0.1536(3) 0.0303(15) Uani 1 1 d . . . . .
C42 C 0.5427(4) 0.8557(11) 0.1882(3) 0.0344(16) Uani 1 1 d . . . . .
H42 H 0.5394 0.7359 0.1694 0.041 Uiso 1 1 calc R U . . .
C43 C 0.6030(5) 0.8719(13) 0.2513(3) 0.0389(17) Uani 1 1 d . . . . .
C44 C 0.6086(6) 1.0448(14) 0.2807(4) 0.050(2) Uani 1 1 d . . . . .
H44 H 0.6489 1.0513 0.3229 0.060 Uiso 1 1 calc R U . . .
C45 C 0.5539(6) 1.2087(14) 0.2469(4) 0.051(2) Uani 1 1 d . . . . .
H45 H 0.5561 1.3264 0.2659 0.062 Uiso 1 1 calc R U . . .
C46 C 0.4958(5) 1.1943(12) 0.1843(3) 0.0413(18) Uani 1 1 d . . . . .
C47 C 0.4245(4) 1.0235(9) 0.0847(3) 0.0273(14) Uani 1 1 d . . . . .
H47 H 0.3801 1.1238 0.0708 0.033 Uiso 1 1 calc R U . . .
Br3 Br -0.19382(7) 0.01381(18) 0.10227(5) 0.0730(4) Uani 1 1 d . . . . .
S7 S 0.05820(15) 0.0369(3) 0.07206(9) 0.0501(6) Uani 1 1 d . . . . .
F1 F 0.0597(4) 0.6985(8) 0.2120(3) 0.0764(17) Uani 1 1 d . . . . .
O1 O 0.1244(4) 0.4927(8) 0.1109(3) 0.0455(13) Uani 1 1 d D . . . .
N1 N 0.1727(4) -0.1424(9) 0.1808(3) 0.0358(14) Uani 1 1 d . . . . .
N2 N 0.1303(4) 0.1691(9) 0.1850(2) 0.0335(13) Uani 1 1 d . . . . .
C1 C 0.1923(4) 0.0997(11) 0.2448(3) 0.0327(16) Uani 1 1 d . . . . .
C2 C 0.2281(5) 0.1919(13) 0.2996(3) 0.0403(18) Uani 1 1 d . . . . .
H2 H 0.2111 0.3223 0.3012 0.048 Uiso 1 1 calc R U . . .
C3 C 0.2910(5) 0.0787(15) 0.3521(3) 0.050(2) Uani 1 1 d . . . . .
H3 H 0.3167 0.1342 0.3898 0.060 Uiso 1 1 calc R U . . .
C4 C 0.3159(6) -0.1154(16) 0.3490(4) 0.055(2) Uani 1 1 d . . . . .
H4 H 0.3576 -0.1876 0.3848 0.066 Uiso 1 1 calc R U . . .
C5 C 0.2810(5) -0.2039(14) 0.2948(4) 0.049(2) Uani 1 1 d . . . . .
H5 H 0.2989 -0.3337 0.2936 0.059 Uiso 1 1 calc R U . . .
C6 C 0.2178(5) -0.0943(11) 0.2411(3) 0.0378(17) Uani 1 1 d . . . . .
C7 C 0.1231(4) 0.0185(10) 0.1502(3) 0.0298(15) Uani 1 1 d . . . . .
C8 C 0.0022(5) 0.2773(12) 0.0561(3) 0.0393(17) Uani 1 1 d . . . . .
H8A H -0.0184 0.3338 0.0181 0.047 Uiso 1 1 calc R U . . .
H8B H -0.0468 0.2474 0.0509 0.047 Uiso 1 1 calc R U . . .
C9 C 0.0564(5) 0.4400(11) 0.1054(3) 0.0346(16) Uani 1 1 d . . . . .
H9 H 0.0214 0.5644 0.0923 0.041 Uiso 1 1 calc R U . . .
C10 C 0.0866(5) 0.3698(10) 0.1669(3) 0.0344(16) Uani 1 1 d . . . . .
H10 H 0.1289 0.4714 0.1974 0.041 Uiso 1 1 calc R U . . .
C11 C 0.0164(4) 0.3681(11) 0.1672(3) 0.0311(15) Uani 1 1 d . . . . .
C12 C 0.0048(6) 0.5342(13) 0.1893(4) 0.052(2) Uani 1 1 d . . . . .
C13 C -0.0591(7) 0.5492(16) 0.1900(5) 0.068(3) Uani 1 1 d . . . . .
H13 H -0.0627 0.6637 0.2070 0.081 Uiso 1 1 calc R U . . .
C14 C -0.1169(6) 0.3898(16) 0.1646(5) 0.061(3) Uani 1 1 d . . . . .
H14 H -0.1609 0.3957 0.1639 0.073 Uiso 1 1 calc R U . . .
C15 C -0.1095(5) 0.2218(14) 0.1404(4) 0.047(2) Uani 1 1 d . . . . .
C16 C -0.0423(5) 0.2056(12) 0.1430(3) 0.0416(18) Uani 1 1 d . . . . .
H16 H -0.0363 0.0865 0.1287 0.050 Uiso 1 1 calc R U . . .
H1A H 0.137(5) 0.608(4) 0.126(2) 0.07(3) Uiso 1 1 d D . . . .
H3A H 0.385(2) 1.251(5) 0.0031(19) 0.07(3) Uiso 1 1 d 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
Br1 C43 1.888(8) . ?
S6 C38 1.745(7) . ?
S6 C39 1.813(7) . ?
F3 C46 1.361(9) . ?
O3 C40 1.428(8) . ?
O3 H3A 0.8100(11) . ?
N5 C38 1.317(9) . ?
N5 C37 1.395(9) . ?
N6 C38 1.364(8) . ?
N6 C32 1.388(9) . ?
N6 C47 1.465(8) . ?
C32 C37 1.386(10) . ?
C32 C33 1.405(10) . ?
C33 C34 1.382(11) . ?
C33 H33 0.9300 . ?
C34 C35 1.399(12) . ?
C34 H34 0.9300 . ?
C35 C36 1.375(12) . ?
C35 H35 0.9300 . ?
C36 C37 1.399(11) . ?
C36 H36 0.9300 . ?
C39 C40 1.522(10) . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C40 C47 1.545(9) . ?
C40 H40 0.9800 . ?
C41 C46 1.384(10) . ?
C41 C42 1.390(10) . ?
C41 C47 1.518(9) . ?
C42 C43 1.394(10) . ?
C42 H42 0.9300 . ?
C43 C44 1.374(11) . ?
C44 C45 1.379(12) . ?
C44 H44 0.9300 . ?
C45 C46 1.382(11) . ?
C45 H45 0.9300 . ?
C47 H47 0.9800 . ?
Br3 C15 1.888(8) . ?
S7 C7 1.736(7) . ?
S7 C8 1.813(8) . ?
F1 C12 1.371(10) . ?
O1 C9 1.395(9) . ?
O1 H1A 0.8100(11) . ?
N1 C7 1.312(9) . ?
N1 C6 1.387(9) . ?
N2 C7 1.355(9) . ?
N2 C1 1.396(9) . ?
N2 C10 1.467(9) . ?
C1 C2 1.388(10) . ?
C1 C6 1.398(11) . ?
C2 C3 1.395(11) . ?
C2 H2 0.9300 . ?
C3 C4 1.387(13) . ?
C3 H3 0.9300 . ?
C4 C5 1.370(12) . ?
C4 H4 0.9300 . ?
C5 C6 1.402(11) . ?
C5 H5 0.9300 . ?
C8 C9 1.517(10) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.548(10) . ?
C9 H9 0.9800 . ?
C10 C11 1.512(10) . ?
C10 H10 0.9800 . ?
C11 C12 1.369(11) . ?
C11 C16 1.402(10) . ?
C12 C13 1.386(13) . ?
C13 C14 1.374(14) . ?
C13 H13 0.9300 . ?
C14 C15 1.373(13) . ?
C14 H14 0.9300 . ?
C15 C16 1.391(11) . ?
C16 H16 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
C38 S6 C39 100.5(3) . . ?
C40 O3 H3A 95(3) . . ?
C38 N5 C37 104.5(6) . . ?
C38 N6 C32 106.0(5) . . ?
C38 N6 C47 128.8(5) . . ?
C32 N6 C47 125.2(5) . . ?
C37 C32 N6 105.9(6) . . ?
C37 C32 C33 123.4(7) . . ?
N6 C32 C33 130.7(7) . . ?
C34 C33 C32 115.6(7) . . ?
C34 C33 H33 122.2 . . ?
C32 C33 H33 122.2 . . ?
C33 C34 C35 122.2(8) . . ?
C33 C34 H34 118.9 . . ?
C35 C34 H34 118.9 . . ?
C36 C35 C34 120.9(8) . . ?
C36 C35 H35 119.5 . . ?
C34 C35 H35 119.5 . . ?
C35 C36 C37 118.7(8) . . ?
C35 C36 H36 120.6 . . ?
C37 C36 H36 120.6 . . ?
C32 C37 N5 110.0(6) . . ?
C32 C37 C36 119.1(7) . . ?
N5 C37 C36 130.8(7) . . ?
N5 C38 N6 113.6(6) . . ?
N5 C38 S6 122.0(5) . . ?
N6 C38 S6 124.4(5) . . ?
C40 C39 S6 113.2(5) . . ?
C40 C39 H39A 108.9 . . ?
S6 C39 H39A 108.9 . . ?
C40 C39 H39B 108.9 . . ?
S6 C39 H39B 108.9 . . ?
H39A C39 H39B 107.7 . . ?
O3 C40 C39 108.8(5) . . ?
O3 C40 C47 111.0(5) . . ?
C39 C40 C47 112.5(5) . . ?
O3 C40 H40 108.2 . . ?
C39 C40 H40 108.2 . . ?
C47 C40 H40 108.2 . . ?
C46 C41 C42 117.5(6) . . ?
C46 C41 C47 119.2(6) . . ?
C42 C41 C47 123.0(6) . . ?
C41 C42 C43 119.3(7) . . ?
C41 C42 H42 120.3 . . ?
C43 C42 H42 120.3 . . ?
C44 C43 C42 121.9(7) . . ?
C44 C43 Br1 118.5(6) . . ?
C42 C43 Br1 119.5(6) . . ?
C43 C44 C45 119.4(7) . . ?
C43 C44 H44 120.3 . . ?
C45 C44 H44 120.3 . . ?
C44 C45 C46 118.5(7) . . ?
C44 C45 H45 120.7 . . ?
C46 C45 H45 120.7 . . ?
F3 C46 C45 118.4(7) . . ?
F3 C46 C41 118.3(6) . . ?
C45 C46 C41 123.3(7) . . ?
N6 C47 C41 112.5(5) . . ?
N6 C47 C40 110.8(5) . . ?
C41 C47 C40 111.6(6) . . ?
N6 C47 H47 107.2 . . ?
C41 C47 H47 107.2 . . ?
C40 C47 H47 107.2 . . ?
C7 S7 C8 101.2(3) . . ?
C9 O1 H1A 102(7) . . ?
C7 N1 C6 104.6(6) . . ?
C7 N2 C1 105.8(6) . . ?
C7 N2 C10 129.5(6) . . ?
C1 N2 C10 124.7(6) . . ?
C2 C1 N2 131.5(7) . . ?
C2 C1 C6 123.1(7) . . ?
N2 C1 C6 105.4(6) . . ?
C1 C2 C3 116.4(8) . . ?
C1 C2 H2 121.8 . . ?
C3 C2 H2 121.8 . . ?
C4 C3 C2 121.1(8) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C5 C4 C3 122.0(8) . . ?
C5 C4 H4 119.0 . . ?
C3 C4 H4 119.0 . . ?
C4 C5 C6 118.4(8) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
N1 C6 C1 109.9(6) . . ?
N1 C6 C5 131.2(7) . . ?
C1 C6 C5 118.9(7) . . ?
N1 C7 N2 114.3(6) . . ?
N1 C7 S7 121.6(5) . . ?
N2 C7 S7 124.0(5) . . ?
C9 C8 S7 113.7(5) . . ?
C9 C8 H8A 108.8 . . ?
S7 C8 H8A 108.8 . . ?
C9 C8 H8B 108.8 . . ?
S7 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
O1 C9 C8 109.2(6) . . ?
O1 C9 C10 111.9(6) . . ?
C8 C9 C10 112.5(6) . . ?
O1 C9 H9 107.7 . . ?
C8 C9 H9 107.7 . . ?
C10 C9 H9 107.7 . . ?
N2 C10 C11 112.3(6) . . ?
N2 C10 C9 110.1(5) . . ?
C11 C10 C9 113.4(6) . . ?
N2 C10 H10 106.9 . . ?
C11 C10 H10 106.9 . . ?
C9 C10 H10 106.9 . . ?
C12 C11 C16 116.1(7) . . ?
C12 C11 C10 120.5(7) . . ?
C16 C11 C10 123.3(6) . . ?
C11 C12 F1 117.8(7) . . ?
C11 C12 C13 124.7(8) . . ?
F1 C12 C13 117.5(8) . . ?
C14 C13 C12 117.9(8) . . ?
C14 C13 H13 121.0 . . ?
C12 C13 H13 121.0 . . ?
C15 C14 C13 119.8(8) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 121.2(8) . . ?
C14 C15 Br3 118.2(6) . . ?
C16 C15 Br3 120.7(7) . . ?
C15 C16 C11 120.3(7) . . ?
C15 C16 H16 119.9 . . ?
C11 C16 H16 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
C38 N6 C32 C37 -0.2(7) . . . . ?
C47 N6 C32 C37 178.6(6) . . . . ?
C38 N6 C32 C33 178.8(7) . . . . ?
C47 N6 C32 C33 -2.3(11) . . . . ?
C37 C32 C33 C34 2.2(10) . . . . ?
N6 C32 C33 C34 -176.7(7) . . . . ?
C32 C33 C34 C35 -0.5(11) . . . . ?
C33 C34 C35 C36 -1.4(13) . . . . ?
C34 C35 C36 C37 1.6(12) . . . . ?
N6 C32 C37 N5 -0.3(7) . . . . ?
C33 C32 C37 N5 -179.4(6) . . . . ?
N6 C32 C37 C36 177.0(6) . . . . ?
C33 C32 C37 C36 -2.1(11) . . . . ?
C38 N5 C37 C32 0.6(7) . . . . ?
C38 N5 C37 C36 -176.2(8) . . . . ?
C35 C36 C37 C32 0.1(11) . . . . ?
C35 C36 C37 N5 176.8(8) . . . . ?
C37 N5 C38 N6 -0.8(7) . . . . ?
C37 N5 C38 S6 180.0(5) . . . . ?
C32 N6 C38 N5 0.7(7) . . . . ?
C47 N6 C38 N5 -178.1(6) . . . . ?
C32 N6 C38 S6 179.9(5) . . . . ?
C47 N6 C38 S6 1.1(9) . . . . ?
C39 S6 C38 N5 -174.2(6) . . . . ?
C39 S6 C38 N6 6.7(6) . . . . ?
C38 S6 C39 C40 -37.8(5) . . . . ?
S6 C39 C40 O3 -58.7(6) . . . . ?
S6 C39 C40 C47 64.7(6) . . . . ?
C46 C41 C42 C43 0.1(10) . . . . ?
C47 C41 C42 C43 175.2(6) . . . . ?
C41 C42 C43 C44 1.3(11) . . . . ?
C41 C42 C43 Br1 -177.0(5) . . . . ?
C42 C43 C44 C45 -0.8(12) . . . . ?
Br1 C43 C44 C45 177.5(6) . . . . ?
C43 C44 C45 C46 -0.9(13) . . . . ?
C44 C45 C46 F3 -177.9(8) . . . . ?
C44 C45 C46 C41 2.3(13) . . . . ?
C42 C41 C46 F3 178.3(7) . . . . ?
C47 C41 C46 F3 3.0(11) . . . . ?
C42 C41 C46 C45 -1.9(12) . . . . ?
C47 C41 C46 C45 -177.2(7) . . . . ?
C38 N6 C47 C41 -105.2(7) . . . . ?
C32 N6 C47 C41 76.3(8) . . . . ?
C38 N6 C47 C40 20.5(9) . . . . ?
C32 N6 C47 C40 -158.1(6) . . . . ?
C46 C41 C47 N6 -143.6(7) . . . . ?
C42 C41 C47 N6 41.3(9) . . . . ?
C46 C41 C47 C40 91.2(8) . . . . ?
C42 C41 C47 C40 -83.8(8) . . . . ?
O3 C40 C47 N6 68.7(7) . . . . ?
C39 C40 C47 N6 -53.5(7) . . . . ?
O3 C40 C47 C41 -165.2(5) . . . . ?
C39 C40 C47 C41 72.7(7) . . . . ?
C7 N2 C1 C2 177.3(8) . . . . ?
C10 N2 C1 C2 -0.8(12) . . . . ?
C7 N2 C1 C6 -0.4(7) . . . . ?
C10 N2 C1 C6 -178.5(6) . . . . ?
N2 C1 C2 C3 -178.6(7) . . . . ?
C6 C1 C2 C3 -1.3(11) . . . . ?
C1 C2 C3 C4 0.2(12) . . . . ?
C2 C3 C4 C5 0.7(14) . . . . ?
C3 C4 C5 C6 -0.6(13) . . . . ?
C7 N1 C6 C1 0.6(8) . . . . ?
C7 N1 C6 C5 -178.8(8) . . . . ?
C2 C1 C6 N1 -178.1(7) . . . . ?
N2 C1 C6 N1 -0.1(8) . . . . ?
C2 C1 C6 C5 1.4(11) . . . . ?
N2 C1 C6 C5 179.4(7) . . . . ?
C4 C5 C6 N1 178.9(8) . . . . ?
C4 C5 C6 C1 -0.5(12) . . . . ?
C6 N1 C7 N2 -0.9(8) . . . . ?
C6 N1 C7 S7 176.1(5) . . . . ?
C1 N2 C7 N1 0.9(8) . . . . ?
C10 N2 C7 N1 178.8(7) . . . . ?
C1 N2 C7 S7 -176.1(5) . . . . ?
C10 N2 C7 S7 1.9(11) . . . . ?
C8 S7 C7 N1 176.7(6) . . . . ?
C8 S7 C7 N2 -6.6(7) . . . . ?
C7 S7 C8 C9 35.9(6) . . . . ?
S7 C8 C9 O1 61.9(7) . . . . ?
S7 C8 C9 C10 -63.0(7) . . . . ?
C7 N2 C10 C11 103.4(8) . . . . ?
C1 N2 C10 C11 -79.0(8) . . . . ?
C7 N2 C10 C9 -24.0(10) . . . . ?
C1 N2 C10 C9 153.6(7) . . . . ?
O1 C9 C10 N2 -69.1(7) . . . . ?
C8 C9 C10 N2 54.3(8) . . . . ?
O1 C9 C10 C11 164.2(6) . . . . ?
C8 C9 C10 C11 -72.4(7) . . . . ?
N2 C10 C11 C12 138.6(7) . . . . ?
C9 C10 C11 C12 -95.9(8) . . . . ?
N2 C10 C11 C16 -44.4(9) . . . . ?
C9 C10 C11 C16 81.1(8) . . . . ?
C16 C11 C12 F1 -178.4(7) . . . . ?
C10 C11 C12 F1 -1.2(12) . . . . ?
C16 C11 C12 C13 0.9(13) . . . . ?
C10 C11 C12 C13 178.1(9) . . . . ?
C11 C12 C13 C14 -2.5(16) . . . . ?
F1 C12 C13 C14 176.9(9) . . . . ?
C12 C13 C14 C15 0.7(16) . . . . ?
C13 C14 C15 C16 2.6(14) . . . . ?
C13 C14 C15 Br3 -176.7(8) . . . . ?
C14 C15 C16 C11 -4.2(12) . . . . ?
Br3 C15 C16 C11 175.1(5) . . . . ?
C12 C11 C16 C15 2.4(11) . . . . ?
C10 C11 C16 C15 -174.7(7) . . . . ?

_refine_diff_density_max         0.873
_refine_diff_density_min         -1.000
_refine_diff_density_rms         0.128


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ehtylacetate'
####################################################################### 
# 
# 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_newp21c
_database_code_depnum_ccdc_archive 'CCDC 1961868'
loop_
_audit_author_name
_audit_author_address
'Bipul Sarma'
;Tezpur University
India
;
_audit_update_record             
;
2019-10-29 deposited with the CCDC.	2019-12-12 downloaded from the CCDC.
;
_vrf_PLAT601_newp21c             
;
PROBLEM: Structure Contains Solvent Accessible VOIDS of 94 Ang**3 
RESPONSE: Structure contains disordered solvent molecules and removed using
PLATON SQUEEZE program. The sample diffracted very weakly because they
form bad quality small needles and gets opauque soon it expose. Moreover
high angle reflections are of very poor quality.  
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H21 N3 O2 S2'
_chemical_formula_weight         435.55

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                   12.881(3)
_cell_length_b                   19.724(4)
_cell_length_c                   9.3055(19)
_cell_angle_alpha                90
_cell_angle_beta                 101.12(3)
_cell_angle_gamma                90
_cell_volume                     2319.7(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3801
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      18.43

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_F_000             888
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.252
_shelx_estimated_absorpt_T_min   0.908
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   SADABS
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            72807
_diffrn_reflns_av_unetI/netI     0.0654
_diffrn_reflns_av_R_equivalents  0.1010
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.611
_diffrn_reflns_theta_max         28.310
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             5621
_reflns_number_gt                2698
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_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          SQUEEZE
_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     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5621
_refine_ls_number_parameters     309
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1951
_refine_ls_R_factor_gt           0.0974
_refine_ls_wR_factor_ref         0.1267
_refine_ls_wR_factor_gt          0.1191
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_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 0.33368(7) 0.22838(4) 1.09118(11) 0.0796(3) Uani 1 1 d . . . . .
S2 S 0.28152(9) 0.48440(6) 0.88290(17) 0.1144(5) Uani 1 1 d . . . . .
N1 N 0.4854(2) 0.17399(13) 0.9686(3) 0.0662(8) Uani 1 1 d . . . . .
N2 N 0.4908(2) 0.28745(13) 0.9734(3) 0.0693(8) Uani 1 1 d . . . . .
C7 C 0.4429(2) 0.23012(18) 1.0072(3) 0.0603(8) Uani 1 1 d . . . . .
C1 C 0.5716(3) 0.26699(19) 0.9020(4) 0.0710(10) Uani 1 1 d . . . . .
C10 C 0.2994(3) 0.31789(15) 1.1055(3) 0.0702(10) Uani 1 1 d . . . . .
H10 H 0.3332 0.3342 1.2027 0.084 Uiso 1 1 calc R U . . .
C6 C 0.5664(3) 0.19667(19) 0.9021(4) 0.0669(9) Uani 1 1 d . . . . .
C9 C 0.3387(2) 0.36167(14) 0.9896(4) 0.0577(9) Uani 1 1 d . . . . .
H9 H 0.3024 0.3475 0.8918 0.069 Uiso 1 1 calc R U . A 2
C17 C 0.1541(3) 0.46409(16) 0.7955(4) 0.0716(11) Uani 1 1 d . . . . .
C8 C 0.4575(2) 0.35709(16) 0.9983(4) 0.0844(11) Uani 1 1 d . . . . .
H8A H 0.4777 0.3869 0.9256 0.101 Uiso 1 1 calc R U . . .
H8B H 0.4936 0.3723 1.0941 0.101 Uiso 1 1 calc R U . . .
C11 C 0.1794(4) 0.31979(17) 1.0950(5) 0.0772(11) Uani 1 1 d . . . . .
C2 C 0.6433(3) 0.3033(2) 0.8416(5) 0.1070(15) Uani 1 1 d . . . . .
H2 H 0.6462 0.3504 0.8449 0.128 Uiso 1 1 calc R U . B 2
O1A O 0.3651(6) 0.4835(3) 0.8219(8) 0.088(2) Uani 0.5 1 d . . P C 1
O1B O 0.3269(6) 0.4561(4) 0.7290(8) 0.126(3) Uani 0.5 1 d . . P C 2
O2A O 0.2760(9) 0.5488(5) 0.9872(9) 0.090(3) Uani 0.5 1 d . . P C 1
O2B O 0.2831(11) 0.5507(6) 0.8976(11) 0.131(5) Uani 0.5 1 d . . P C 2
C5 C 0.6383(3) 0.1592(2) 0.8363(4) 0.0871(12) Uani 1 1 d . . . D 2
H5 H 0.6383 0.1121 0.8357 0.105 Uiso 1 1 calc R U . D 2
C4 C 0.7081(3) 0.1960(3) 0.7734(5) 0.1067(14) Uani 1 1 d . . . D 2
H4 H 0.7554 0.1727 0.7274 0.128 Uiso 1 1 calc R U . D 2
C16 C 0.1138(4) 0.2966(2) 0.9704(6) 0.1077(14) Uani 1 1 d . . . E 2
H16 H 0.1434 0.2794 0.8944 0.129 Uiso 1 1 calc R U . E 2
C3 C 0.7113(3) 0.2651(3) 0.7751(5) 0.1188(16) Uani 1 1 d . . . D 2
H3 H 0.7605 0.2872 0.7305 0.143 Uiso 1 1 calc R U . D 2
C12 C 0.1361(5) 0.3456(3) 1.2043(6) 0.154(2) Uani 1 1 d . . . E 2
H12 H 0.1798 0.3626 1.2879 0.184 Uiso 1 1 calc R U . E 2
C15 C 0.0030(4) 0.2983(2) 0.9551(7) 0.1381(19) Uani 1 1 d . . . E 2
H15 H -0.0424 0.2841 0.8703 0.166 Uiso 1 1 calc R U . E 2
C18 C 0.0714(4) 0.4838(3) 0.8498(5) 0.1294(18) Uani 1 1 d . . . F 2
H18 H 0.0815 0.5085 0.9365 0.155 Uiso 1 1 calc R U . F 2
C14 C -0.0314(7) 0.3214(4) 1.0698(11) 0.200(4) Uani 1 1 d . . . E 2
H14 H -0.1043 0.3190 1.0625 0.240 Uiso 1 1 calc R U . E 2
C13 C 0.0203(8) 0.3473(4) 1.1930(8) 0.188(4) Uani 1 1 d . . . E 2
H13 H -0.0126 0.3649 1.2655 0.226 Uiso 1 1 calc R U . E 2
N3 N 0.31070(18) 0.43185(12) 1.0141(3) 0.0786(9) Uani 1 1 d . . . G 2
H3A H 0.3099 0.4452 1.1019 0.094 Uiso 1 1 calc R U . G 2
C19 C -0.0291(5) 0.4681(4) 0.7789(8) 0.163(3) Uani 1 1 d . . . F 2
H19 H -0.0778 0.4861 0.8303 0.196 Uiso 1 1 calc R U . F 2
C20B C -0.0270(8) 0.4250(6) 0.6303(14) 0.078(4) Uani 0.5 1 d . . P H 2
C21 C 0.1400(7) 0.4292(4) 0.6742(7) 0.174(3) Uani 1 1 d . . . H 2
H21 H 0.1982 0.4148 0.6368 0.209 Uiso 1 1 calc R U . H 2
C22A C -0.1910(8) 0.4283(8) 0.6180(16) 0.168(5) Uani 0.5 1 d . . P F 1
H22A H -0.2271 0.4709 0.5977 0.252 Uiso 0.5 1 calc R U P F 1
H22B H -0.2220 0.4033 0.6875 0.252 Uiso 0.5 1 calc R U P F 1
H22C H -0.1974 0.4027 0.5290 0.252 Uiso 0.5 1 calc R U P F 1
C22B C -0.1279(9) 0.4061(7) 0.5395(13) 0.132(4) Uani 0.5 1 d . . P H 2
H22D H -0.1342 0.4267 0.4448 0.197 Uiso 0.5 1 calc R U P H 2
H22E H -0.1845 0.4215 0.5849 0.197 Uiso 0.5 1 calc R U P H 2
H22F H -0.1315 0.3577 0.5290 0.197 Uiso 0.5 1 calc R U P H 2
C23 C 0.0442(10) 0.4143(4) 0.6047(9) 0.211(5) Uani 1 1 d . . . H 2
H23 H 0.0411 0.3900 0.5182 0.253 Uiso 1 1 calc R U . H 2
C20A C -0.0706(10) 0.4416(6) 0.6830(16) 0.096(4) Uani 0.5 1 d . . P . .


_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 C7 1.737(3) . ?
S1 C10 1.831(3) . ?
S2 O1A 1.310(7) . ?
S2 O2B 1.314(12) . ?
S2 N3 1.590(3) . ?
S2 O2A 1.609(10) . ?
S2 C17 1.733(4) . ?
S2 O1B 1.740(7) . ?
N1 C7 1.315(3) . ?
N1 C6 1.386(4) . ?
N2 C7 1.354(4) . ?
N2 C1 1.397(4) . ?
N2 C8 1.471(4) . ?
C1 C2 1.373(4) . ?
C1 C6 1.389(4) . ?
C10 C9 1.541(4) . ?
C10 C11 1.531(4) . ?
C6 C5 1.414(4) . ?
C9 N3 1.459(3) . ?
C9 C8 1.519(4) . ?
C17 C18 1.322(4) . ?
C17 C21 1.305(6) . ?
C11 C12 1.351(5) . ?
C11 C16 1.375(5) . ?
C2 C3 1.388(5) . ?
C5 C4 1.371(5) . ?
C4 C3 1.364(5) . ?
C16 C15 1.407(5) . ?
C12 C13 1.475(9) . ?
C15 C14 1.314(7) . ?
C18 C19 1.370(6) . ?
C14 C13 1.314(10) . ?
C19 C20A 1.082(13) . ?
C20B C23 1.014(10) . ?
C20B C22B 1.454(16) . ?
C21 C23 1.311(9) . ?
C22A C20A 1.574(17) . ?
C23 C20A 1.851(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 S1 C10 103.95(17) . . ?
O2B S2 N3 124.9(5) . . ?
O1A S2 O2A 114.1(5) . . ?
O1A S2 C17 125.2(3) . . ?
O2B S2 C17 105.9(6) . . ?
N3 S2 C17 105.78(15) . . ?
O2A S2 C17 108.5(4) . . ?
O2B S2 O1B 113.8(5) . . ?
N3 S2 O1B 110.8(3) . . ?
C17 S2 O1B 88.7(3) . . ?
C7 N1 C6 103.8(3) . . ?
C7 N2 C1 106.5(3) . . ?
C7 N2 C8 125.7(3) . . ?
C1 N2 C8 127.7(3) . . ?
N1 C7 N2 114.1(3) . . ?
N1 C7 S1 121.4(3) . . ?
N2 C7 S1 124.5(3) . . ?
C2 C1 N2 131.8(4) . . ?
C2 C1 C6 123.9(4) . . ?
N2 C1 C6 104.3(3) . . ?
C9 C10 C11 113.9(2) . . ?
C9 C10 S1 111.9(2) . . ?
C11 C10 S1 105.9(2) . . ?
C1 C6 N1 111.3(3) . . ?
C1 C6 C5 119.0(4) . . ?
N1 C6 C5 129.6(4) . . ?
N3 C9 C8 109.0(2) . . ?
N3 C9 C10 107.3(2) . . ?
C8 C9 C10 113.1(3) . . ?
C18 C17 C21 119.9(5) . . ?
C18 C17 S2 120.8(4) . . ?
C21 C17 S2 119.3(5) . . ?
N2 C8 C9 111.7(2) . . ?
C12 C11 C16 119.0(5) . . ?
C12 C11 C10 121.3(5) . . ?
C16 C11 C10 119.6(3) . . ?
C1 C2 C3 115.6(4) . . ?
C4 C5 C6 116.6(4) . . ?
C5 C4 C3 123.0(4) . . ?
C15 C16 C11 121.6(5) . . ?
C4 C3 C2 121.8(4) . . ?
C11 C12 C13 120.9(6) . . ?
C14 C15 C16 114.9(7) . . ?
C17 C18 C19 120.3(5) . . ?
C15 C14 C13 130.6(10) . . ?
C14 C13 C12 112.9(7) . . ?
C9 N3 S2 121.8(2) . . ?
C20A C19 C18 141.0(11) . . ?
C23 C20B C22B 123.9(13) . . ?
C23 C21 C17 120.3(8) . . ?
C20B C23 C21 130.2(13) . . ?
C20B C23 C20A 11.0(9) . . ?
C21 C23 C20A 119.2(9) . . ?
C19 C20A C23 99.2(11) . . ?

_refine_diff_density_max         0.440
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.049


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ehtylacetate'
_chemical_properties_physical    Hygroscopic
