# 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_Compd3aa
_database_code_depnum_ccdc_archive 'CCDC 1857227'
loop_
_audit_author_name
_audit_author_address
'K C Kumara Swamy'
;University of Hyderabad
India
;
_audit_update_record             
;
2018-07-21 deposited with the CCDC.	2019-06-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H14 N2 O2 S2'
_chemical_formula_weight         318.40

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'

_symmetry_cell_setting           Orthorhombic'
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   11.4990(8)
_cell_length_b                   8.4660(6)
_cell_length_c                   31.300(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3047.1(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9952
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      26.47

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1328
_exptl_absorpt_coefficient_mu    0.354
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_process_details   'SADABS, Sheldrick (1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22816
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_sigmaI/netI    0.0129
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         3.15
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2649
_reflns_number_gt                2379
_reflns_threshold_expression     >2sigma(I)

_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 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0475P)²+1.0770P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2649
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0338
_refine_ls_wR_factor_ref         0.0919
_refine_ls_wR_factor_gt          0.0893
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S2 S 0.50962(4) 0.35353(6) 0.340712(13) 0.04782(16) Uani 1 1 d . . .
S1 S 0.40018(4) 0.51579(5) 0.423200(14) 0.04663(16) Uani 1 1 d . . .
O2 O 0.32505(14) 0.53480(19) 0.45901(4) 0.0682(4) Uani 1 1 d . . .
N2 N 0.30550(13) 0.45147(18) 0.30899(4) 0.0450(4) Uani 1 1 d . . .
O1 O 0.47471(15) 0.64300(17) 0.41168(5) 0.0662(4) Uani 1 1 d . . .
N1 N 0.31727(13) 0.4671(2) 0.38206(4) 0.0475(4) Uani 1 1 d . . .
C6 C 0.52980(14) 0.2759(2) 0.39251(5) 0.0383(4) Uani 1 1 d . . .
C7 C 0.36614(15) 0.4327(2) 0.34207(5) 0.0395(4) Uani 1 1 d . . .
C1 C 0.48260(15) 0.3448(2) 0.42896(5) 0.0393(4) Uani 1 1 d . . .
C5 C 0.59818(15) 0.1423(2) 0.39688(6) 0.0446(4) Uani 1 1 d . . .
H5 H 0.6286 0.0938 0.3727 0.054 Uiso 1 1 calc R . .
C8 C 0.34622(15) 0.4042(2) 0.26804(5) 0.0409(4) Uani 1 1 d . . .
C2 C 0.50297(16) 0.2811(2) 0.46913(6) 0.0486(5) Uani 1 1 d . . .
H2 H 0.4691 0.3256 0.4933 0.058 Uiso 1 1 calc R . .
C3 C 0.57413(18) 0.1508(2) 0.47270(6) 0.0541(5) Uani 1 1 d . . .
H3 H 0.5903 0.1099 0.4996 0.065 Uiso 1 1 calc R . .
C13 C 0.28355(18) 0.2911(2) 0.24616(6) 0.0542(5) Uani 1 1 d . . .
H13 H 0.2176 0.2467 0.2585 0.065 Uiso 1 1 calc R . .
C4 C 0.62206(16) 0.0796(2) 0.43702(6) 0.0498(5) Uani 1 1 d . . .
C9 C 0.44195(18) 0.4728(2) 0.24892(6) 0.0521(5) Uani 1 1 d . . .
H9 H 0.4834 0.5511 0.2632 0.063 Uiso 1 1 calc R . .
C11 C 0.4153(2) 0.3106(3) 0.18711(6) 0.0663(6) Uani 1 1 d . . .
H11 H 0.4389 0.2783 0.1601 0.080 Uiso 1 1 calc R . .
C10 C 0.4761(2) 0.4254(3) 0.20870(7) 0.0632(6) Uani 1 1 d . . .
H10 H 0.5410 0.4714 0.1961 0.076 Uiso 1 1 calc R . .
C12 C 0.3188(2) 0.2441(3) 0.20598(7) 0.0675(6) Uani 1 1 d . . .
H12 H 0.2770 0.1667 0.1915 0.081 Uiso 1 1 calc R . .
C15 C 0.19216(18) 0.4979(3) 0.38405(7) 0.0688(6) Uani 1 1 d . . .
H15A H 0.1740 0.5891 0.3671 0.103 Uiso 1 1 calc R . .
H15B H 0.1698 0.5167 0.4132 0.103 Uiso 1 1 calc R . .
H15C H 0.1506 0.4081 0.3732 0.103 Uiso 1 1 calc R . .
C14 C 0.6976(2) -0.0651(3) 0.44088(8) 0.0756(7) Uani 1 1 d . . .
H14A H 0.7190 -0.0803 0.4702 0.113 Uiso 1 1 calc R . .
H14B H 0.7665 -0.0513 0.4240 0.113 Uiso 1 1 calc R . .
H14C H 0.6556 -0.1558 0.4309 0.113 Uiso 1 1 calc R . .


_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
S2 C6 1.7648(17) . ?
S2 C7 1.7815(17) . ?
S1 O1 1.4228(16) . ?
S1 O2 1.4243(14) . ?
S1 N1 1.6542(15) . ?
S1 C1 1.7396(18) . ?
N2 C7 1.258(2) . ?
N2 C8 1.422(2) . ?
N1 C7 1.403(2) . ?
N1 C15 1.463(2) . ?
C6 C5 1.384(2) . ?
C6 C1 1.392(2) . ?
C1 C2 1.388(2) . ?
C5 C4 1.391(3) . ?
C5 H5 0.9300 . ?
C8 C13 1.380(3) . ?
C8 C9 1.381(3) . ?
C2 C3 1.378(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.384(3) . ?
C3 H3 0.9300 . ?
C13 C12 1.380(3) . ?
C13 H13 0.9300 . ?
C4 C14 1.507(3) . ?
C9 C10 1.379(3) . ?
C9 H9 0.9300 . ?
C11 C10 1.375(3) . ?
C11 C12 1.377(3) . ?
C11 H11 0.9300 . ?
C10 H10 0.9300 . ?
C12 H12 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
C6 S2 C7 103.89(8) . . ?
O1 S1 O2 118.64(10) . . ?
O1 S1 N1 109.77(9) . . ?
O2 S1 N1 106.93(9) . . ?
O1 S1 C1 109.15(9) . . ?
O2 S1 C1 110.05(9) . . ?
N1 S1 C1 100.81(8) . . ?
C7 N2 C8 121.58(15) . . ?
C7 N1 C15 117.95(15) . . ?
C7 N1 S1 121.02(12) . . ?
C15 N1 S1 119.29(13) . . ?
C5 C6 C1 118.89(16) . . ?
C5 C6 S2 118.01(13) . . ?
C1 C6 S2 123.08(13) . . ?
N2 C7 N1 119.09(15) . . ?
N2 C7 S2 122.75(13) . . ?
N1 C7 S2 118.06(12) . . ?
C2 C1 C6 120.92(17) . . ?
C2 C1 S1 120.63(14) . . ?
C6 C1 S1 118.44(13) . . ?
C6 C5 C4 120.86(17) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C13 C8 C9 119.53(17) . . ?
C13 C8 N2 118.07(17) . . ?
C9 C8 N2 122.32(16) . . ?
C3 C2 C1 119.02(17) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 121.31(17) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C12 C13 C8 119.9(2) . . ?
C12 C13 H13 120.0 . . ?
C8 C13 H13 120.0 . . ?
C3 C4 C5 118.96(18) . . ?
C3 C4 C14 121.27(18) . . ?
C5 C4 C14 119.76(19) . . ?
C10 C9 C8 120.02(19) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C10 C11 C12 119.22(19) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C11 C10 C9 120.6(2) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C11 C12 C13 120.6(2) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C4 C14 H14A 109.5 . . ?
C4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.037
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_Compd3cc
_database_code_depnum_ccdc_archive 'CCDC 1857228'
loop_
_audit_author_name
_audit_author_address
'K C Kumara Swamy'
;University of Hyderabad
India
;
_audit_update_record             
;
2018-07-21 deposited with the CCDC.	2019-06-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H15 F3 N2 O2 S2'
_chemical_formula_weight         448.47

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'

_symmetry_cell_setting           Monoclinic'
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   18.7734(9)
_cell_length_b                   12.5873(5)
_cell_length_c                   8.6595(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.548(2)
_cell_angle_gamma                90.00
_cell_volume                     2036.71(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    9952
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      26.47

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             920
_exptl_absorpt_coefficient_mu    0.309
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_process_details   'SADABS, Sheldrick (1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20455
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_sigmaI/netI    0.0216
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.72
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3563
_reflns_number_gt                2861
_reflns_threshold_expression     >2sigma(I)

_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 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0570P)²+0.9033P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3563
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.1194
_refine_ls_wR_factor_gt          0.1115
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.004
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.86156(3) 0.56232(5) 0.86005(7) 0.0588(2) Uani 1 1 d . . .
S2 S 0.82353(3) 0.47384(6) 0.38887(7) 0.0613(2) Uani 1 1 d . . .
O1 O 0.83101(9) 0.66492(14) 0.8449(2) 0.0716(5) Uani 1 1 d . . .
O2 O 0.93220(9) 0.55047(16) 0.9314(2) 0.0785(6) Uani 1 1 d . . .
N1 N 0.86314(10) 0.51142(17) 0.6799(2) 0.0566(5) Uani 1 1 d . . .
N2 N 0.74602(11) 0.5669(2) 0.6004(2) 0.0684(6) Uani 1 1 d . . .
C7 C 0.91752(11) 0.44415(17) 0.6283(3) 0.0482(5) Uani 1 1 d . . .
C8 C 0.97869(12) 0.4056(2) 0.7119(3) 0.0576(6) Uani 1 1 d . . .
H8 H 0.9888 0.4220 0.8164 0.069 Uiso 1 1 calc R . .
C1 C 0.80479(13) 0.47588(19) 0.9475(3) 0.0562(6) Uani 1 1 d . . .
C9 C 1.02425(13) 0.34228(19) 0.6366(3) 0.0576(6) Uani 1 1 d . . .
H9 H 1.0656 0.3162 0.6916 0.069 Uiso 1 1 calc R . .
C13 C 0.80432(12) 0.52642(19) 0.5684(3) 0.0539(6) Uani 1 1 d . . .
C12 C 0.90335(12) 0.41828(18) 0.4734(3) 0.0515(5) Uani 1 1 d . . .
C14 C 0.69164(12) 0.5866(2) 0.4799(3) 0.0569(6) Uani 1 1 d . . .
C17 C 0.57984(14) 0.6338(2) 0.2579(3) 0.0668(7) Uani 1 1 d . . .
C2 C 0.73568(14) 0.5056(2) 0.9690(3) 0.0624(6) Uani 1 1 d . . .
H2 H 0.7184 0.5717 0.9354 0.075 Uiso 1 1 calc R . .
C16 C 0.64367(15) 0.6871(2) 0.2601(3) 0.0718(7) Uani 1 1 d . . .
H16 H 0.6494 0.7397 0.1869 0.086 Uiso 1 1 calc R . .
C10 C 1.01024(14) 0.3168(2) 0.4833(3) 0.0629(6) Uani 1 1 d . . .
H10 H 1.0417 0.2735 0.4355 0.075 Uiso 1 1 calc R . .
C11 C 0.94969(15) 0.3551(2) 0.3997(3) 0.0655(7) Uani 1 1 d . . .
H11 H 0.9401 0.3387 0.2950 0.079 Uiso 1 1 calc R . .
F3 F 0.45968(13) 0.6181(3) 0.1632(4) 0.1705(13) Uani 1 1 d . . .
C6 C 0.83049(16) 0.3772(2) 0.9960(3) 0.0715(8) Uani 1 1 d . . .
H6 H 0.8771 0.3573 0.9818 0.086 Uiso 1 1 calc R . .
C18 C 0.57257(14) 0.5563(3) 0.3647(4) 0.0813(9) Uani 1 1 d . . .
H18 H 0.5299 0.5185 0.3621 0.098 Uiso 1 1 calc R . .
F2 F 0.50574(17) 0.7630(2) 0.1329(4) 0.1777(14) Uani 1 1 d . . .
C19 C 0.62756(14) 0.5331(2) 0.4767(4) 0.0773(8) Uani 1 1 d . . .
H19 H 0.6214 0.4810 0.5505 0.093 Uiso 1 1 calc R . .
F1 F 0.53283(17) 0.6366(3) 0.0000(3) 0.1869(15) Uani 1 1 d . . .
C15 C 0.69917(14) 0.6634(2) 0.3696(3) 0.0667(7) Uani 1 1 d . . .
H15 H 0.7423 0.6996 0.3692 0.080 Uiso 1 1 calc R . .
C3 C 0.69261(15) 0.4367(2) 1.0405(3) 0.0715(7) Uani 1 1 d . . .
H3 H 0.6462 0.4572 1.0560 0.086 Uiso 1 1 calc R . .
C4 C 0.71678(18) 0.3374(2) 1.0898(3) 0.0753(8) Uani 1 1 d . . .
C5 C 0.7862(2) 0.3091(2) 1.0653(3) 0.0828(9) Uani 1 1 d . . .
H5 H 0.8031 0.2423 1.0966 0.099 Uiso 1 1 calc R . .
C21 C 0.5200(2) 0.6607(4) 0.1393(4) 0.1012(11) Uani 1 1 d . . .
C20 C 0.6691(2) 0.2631(3) 1.1695(5) 0.1152(13) Uani 1 1 d . . .
H20A H 0.6979 0.2108 1.2270 0.173 Uiso 1 1 calc R . .
H20B H 0.6367 0.2283 1.0931 0.173 Uiso 1 1 calc R . .
H20C H 0.6424 0.3027 1.2390 0.173 Uiso 1 1 calc R . .


_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 1.4140(18) . ?
S1 O2 1.4158(17) . ?
S1 N1 1.689(2) . ?
S1 C1 1.746(3) . ?
S2 C12 1.749(2) . ?
S2 C13 1.759(2) . ?
N1 C13 1.408(3) . ?
N1 C7 1.431(3) . ?
N2 C13 1.262(3) . ?
N2 C14 1.410(3) . ?
C7 C12 1.381(3) . ?
C7 C8 1.385(3) . ?
C8 C9 1.378(3) . ?
C8 H8 0.9300 . ?
C1 C2 1.380(3) . ?
C1 C6 1.383(4) . ?
C9 C10 1.366(4) . ?
C9 H9 0.9300 . ?
C12 C11 1.380(3) . ?
C14 C15 1.376(4) . ?
C14 C19 1.377(4) . ?
C17 C18 1.359(4) . ?
C17 C16 1.372(4) . ?
C17 C21 1.487(4) . ?
C2 C3 1.373(4) . ?
C2 H2 0.9300 . ?
C16 C15 1.372(4) . ?
C16 H16 0.9300 . ?
C10 C11 1.375(4) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
F3 C21 1.287(5) . ?
C6 C5 1.373(4) . ?
C6 H6 0.9300 . ?
C18 C19 1.378(4) . ?
C18 H18 0.9300 . ?
F2 C21 1.315(5) . ?
C19 H19 0.9300 . ?
F1 C21 1.289(4) . ?
C15 H15 0.9300 . ?
C3 C4 1.383(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.387(4) . ?
C4 C20 1.507(5) . ?
C5 H5 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 119.41(12) . . ?
O1 S1 N1 107.70(11) . . ?
O2 S1 N1 105.31(10) . . ?
O1 S1 C1 110.50(11) . . ?
O2 S1 C1 109.28(13) . . ?
N1 S1 C1 103.31(10) . . ?
C12 S2 C13 91.21(11) . . ?
C13 N1 C7 113.65(18) . . ?
C13 N1 S1 120.01(15) . . ?
C7 N1 S1 126.13(15) . . ?
C13 N2 C14 119.3(2) . . ?
C12 C7 C8 119.8(2) . . ?
C12 C7 N1 111.51(19) . . ?
C8 C7 N1 128.7(2) . . ?
C9 C8 C7 118.5(2) . . ?
C9 C8 H8 120.8 . . ?
C7 C8 H8 120.8 . . ?
C2 C1 C6 120.5(3) . . ?
C2 C1 S1 120.7(2) . . ?
C6 C1 S1 118.8(2) . . ?
C10 C9 C8 121.7(2) . . ?
C10 C9 H9 119.2 . . ?
C8 C9 H9 119.2 . . ?
N2 C13 N1 122.9(2) . . ?
N2 C13 S2 127.04(18) . . ?
N1 C13 S2 109.98(16) . . ?
C11 C12 C7 120.9(2) . . ?
C11 C12 S2 126.15(19) . . ?
C7 C12 S2 112.90(17) . . ?
C15 C14 C19 118.6(2) . . ?
C15 C14 N2 121.5(2) . . ?
C19 C14 N2 119.8(2) . . ?
C18 C17 C16 119.1(2) . . ?
C18 C17 C21 121.0(3) . . ?
C16 C17 C21 119.9(3) . . ?
C3 C2 C1 119.5(3) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C15 C16 C17 120.5(3) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C9 C10 C11 120.1(2) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C10 C11 C12 119.0(2) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
C5 C6 C1 119.0(3) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
C17 C18 C19 120.9(3) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C14 C19 C18 120.2(3) . . ?
C14 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C16 C15 C14 120.7(2) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C2 C3 C4 121.3(3) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C3 C4 C5 118.0(3) . . ?
C3 C4 C20 120.7(3) . . ?
C5 C4 C20 121.2(3) . . ?
C6 C5 C4 121.6(3) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
F3 C21 F1 107.4(4) . . ?
F3 C21 F2 103.7(4) . . ?
F1 C21 F2 104.3(4) . . ?
F3 C21 C17 114.3(3) . . ?
F1 C21 C17 113.3(3) . . ?
F2 C21 C17 112.9(3) . . ?
C4 C20 H20A 109.5 . . ?
C4 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C4 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.038
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_Compd9b
_database_code_depnum_ccdc_archive 'CCDC 1857231'
loop_
_audit_author_name
_audit_author_address
'K C Kumara Swamy'
;University of Hyderabad
India
;
_audit_update_record             
;
2018-07-21 deposited with the CCDC.	2019-06-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H19 F3 N2 O2 S2'
_chemical_formula_weight         428.48

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   14.5408(7)
_cell_length_b                   10.0380(5)
_cell_length_c                   14.7642(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.918(2)
_cell_angle_gamma                90.00
_cell_volume                     1984.88(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9952
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      26.47

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             888
_exptl_absorpt_coefficient_mu    0.313
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_process_details   'SADABS, Sheldrick (1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            48446
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_sigmaI/netI    0.0108
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.78
_diffrn_reflns_theta_max         26.47
_reflns_number_total             4036
_reflns_number_gt                3658
_reflns_threshold_expression     >2sigma(I)

_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 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0540P)²+0.7853P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4036
_refine_ls_number_parameters     257
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0364
_refine_ls_wR_factor_ref         0.1046
_refine_ls_wR_factor_gt          0.1005
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.004
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.80596(3) 0.35805(4) 0.42898(3) 0.03888(13) Uani 1 1 d . . .
S2 S 0.72931(3) 0.37258(5) 0.60310(3) 0.04677(14) Uani 1 1 d . . .
O1 O 0.85089(9) 0.30098(14) 0.36775(9) 0.0521(3) Uani 1 1 d . . .
F1 F 0.39789(11) 0.10445(14) 0.78878(10) 0.0763(4) Uani 1 1 d . . .
F3 F 0.27637(8) 0.18960(16) 0.67068(10) 0.0785(4) Uani 1 1 d . . .
O2 O 0.75843(10) 0.48410(13) 0.40281(10) 0.0557(3) Uani 1 1 d . . .
F2 F 0.38127(11) 0.31615(13) 0.77624(10) 0.0772(4) Uani 1 1 d . . .
N2 N 0.59201(10) 0.21052(15) 0.47969(11) 0.0482(3) Uani 1 1 d . . .
N1 N 0.72560(10) 0.24616(14) 0.43726(10) 0.0426(3) Uani 1 1 d . . .
C1 C 0.89242(11) 0.36350(14) 0.55012(11) 0.0355(3) Uani 1 1 d . . .
C6 C 0.85773(11) 0.37119(14) 0.62555(11) 0.0363(3) Uani 1 1 d . . .
C4 C 1.02821(11) 0.38119(14) 0.74510(11) 0.0375(3) Uani 1 1 d . . .
C7 C 0.67430(11) 0.26787(15) 0.49875(11) 0.0380(3) Uani 1 1 d . . .
C11 C 0.43456(11) 0.20840(16) 0.66382(12) 0.0406(3) Uani 1 1 d . . .
C8 C 0.54220(11) 0.21434(16) 0.54518(12) 0.0423(3) Uani 1 1 d . . .
C2 C 0.99369(12) 0.36106(16) 0.57155(12) 0.0428(4) Uani 1 1 d . . .
H2 H 1.0167 0.3529 0.5212 0.051 Uiso 1 1 calc R . .
C5 C 0.92577(11) 0.37911(15) 0.72197(11) 0.0390(3) Uani 1 1 d . . .
H5 H 0.9026 0.3831 0.7724 0.047 Uiso 1 1 calc R . .
C14 C 1.10325(12) 0.38506(18) 0.85175(12) 0.0462(4) Uani 1 1 d . . .
C12 C 0.41641(14) 0.30636(19) 0.59343(14) 0.0531(4) Uani 1 1 d . . .
H12 H 0.3680 0.3707 0.5860 0.064 Uiso 1 1 calc R . .
C3 C 1.06048(12) 0.37078(17) 0.66782(13) 0.0442(4) Uani 1 1 d . . .
H3 H 1.1286 0.3704 0.6816 0.053 Uiso 1 1 calc R . .
C13 C 0.46970(14) 0.30940(19) 0.53402(14) 0.0529(4) Uani 1 1 d . . .
H13 H 0.4569 0.3754 0.4864 0.064 Uiso 1 1 calc R . .
C19 C 0.37393(13) 0.20499(18) 0.72485(14) 0.0495(4) Uani 1 1 d . . .
C18 C 0.68803(15) 0.1435(2) 0.36107(14) 0.0570(5) Uani 1 1 d . . .
H18A H 0.6652 0.0683 0.3867 0.086 Uiso 1 1 calc R . .
H18B H 0.7406 0.1160 0.3412 0.086 Uiso 1 1 calc R . .
H18C H 0.6337 0.1790 0.3054 0.086 Uiso 1 1 calc R . .
C10 C 0.50666(14) 0.11386(19) 0.67486(16) 0.0569(5) Uani 1 1 d . . .
H10 H 0.5197 0.0481 0.7226 0.068 Uiso 1 1 calc R . .
C9 C 0.55963(14) 0.1166(2) 0.61511(17) 0.0609(5) Uani 1 1 d . . .
H9 H 0.6076 0.0518 0.6222 0.073 Uiso 1 1 calc R . .
C17 C 1.05880(17) 0.4461(3) 0.92023(16) 0.0785(7) Uani 1 1 d . . .
H17A H 1.1093 0.4514 0.9856 0.118 Uiso 1 1 calc R . .
H17B H 1.0048 0.3914 0.9206 0.118 Uiso 1 1 calc R . .
H17C H 1.0343 0.5338 0.8976 0.118 Uiso 1 1 calc R . .
C16 C 1.1316(2) 0.2412(3) 0.88417(19) 0.0902(8) Uani 1 1 d . . .
H16A H 1.1649 0.2026 0.8458 0.135 Uiso 1 1 calc R . .
H16B H 1.0723 0.1910 0.8747 0.135 Uiso 1 1 calc R . .
H16C H 1.1752 0.2395 0.9525 0.135 Uiso 1 1 calc R . .
C15 C 1.19533(18) 0.4646(3) 0.86113(19) 0.0920(9) Uani 1 1 d . . .
H15A H 1.1764 0.5546 0.8402 0.138 Uiso 1 1 calc R . .
H15B H 1.2261 0.4251 0.8207 0.138 Uiso 1 1 calc R . .
H15C H 1.2418 0.4645 0.9285 0.138 Uiso 1 1 calc R . .


_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 1.4212(13) . ?
S1 O1 1.4255(11) . ?
S1 N1 1.6592(14) . ?
S1 C1 1.7411(16) . ?
S2 C6 1.7649(15) . ?
S2 C7 1.7772(16) . ?
F1 C19 1.332(2) . ?
F3 C19 1.339(2) . ?
F2 C19 1.330(2) . ?
N2 C7 1.257(2) . ?
N2 C8 1.416(2) . ?
N1 C7 1.3984(19) . ?
N1 C18 1.465(2) . ?
C1 C2 1.381(2) . ?
C1 C6 1.392(2) . ?
C6 C5 1.384(2) . ?
C4 C5 1.393(2) . ?
C4 C3 1.397(2) . ?
C4 C14 1.528(2) . ?
C11 C10 1.376(2) . ?
C11 C12 1.380(2) . ?
C11 C19 1.486(2) . ?
C8 C9 1.374(3) . ?
C8 C13 1.383(2) . ?
C2 C3 1.378(2) . ?
C2 H2 0.9300 . ?
C5 H5 0.9300 . ?
C14 C15 1.518(2) . ?
C14 C17 1.524(3) . ?
C14 C16 1.527(3) . ?
C12 C13 1.378(3) . ?
C12 H12 0.9300 . ?
C3 H3 0.9300 . ?
C13 H13 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C10 C9 1.379(3) . ?
C10 H10 0.9300 . ?
C9 H9 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 118.68(8) . . ?
O2 S1 N1 109.93(7) . . ?
O1 S1 N1 106.52(7) . . ?
O2 S1 C1 109.36(8) . . ?
O1 S1 C1 109.76(7) . . ?
N1 S1 C1 101.13(7) . . ?
C6 S2 C7 104.14(7) . . ?
C7 N2 C8 122.01(14) . . ?
C7 N1 C18 118.31(14) . . ?
C7 N1 S1 120.75(11) . . ?
C18 N1 S1 118.83(11) . . ?
C2 C1 C6 120.26(15) . . ?
C2 C1 S1 120.93(12) . . ?
C6 C1 S1 118.81(12) . . ?
C5 C6 C1 119.31(14) . . ?
C5 C6 S2 118.23(11) . . ?
C1 C6 S2 122.46(12) . . ?
C5 C4 C3 117.78(14) . . ?
C5 C4 C14 121.31(14) . . ?
C3 C4 C14 120.78(14) . . ?
N2 C7 N1 119.03(14) . . ?
N2 C7 S2 122.19(12) . . ?
N1 C7 S2 118.76(11) . . ?
C10 C11 C12 119.62(15) . . ?
C10 C11 C19 121.12(16) . . ?
C12 C11 C19 119.25(15) . . ?
C9 C8 C13 119.40(15) . . ?
C9 C8 N2 119.99(15) . . ?
C13 C8 N2 120.39(16) . . ?
C3 C2 C1 119.72(14) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C6 C5 C4 121.41(14) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C15 C14 C17 108.35(18) . . ?
C15 C14 C16 110.4(2) . . ?
C17 C14 C16 107.7(2) . . ?
C15 C14 C4 110.97(16) . . ?
C17 C14 C4 112.13(15) . . ?
C16 C14 C4 107.23(15) . . ?
C13 C12 C11 120.35(16) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C2 C3 C4 121.47(14) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C12 C13 C8 120.00(17) . . ?
C12 C13 H13 120.0 . . ?
C8 C13 H13 120.0 . . ?
F2 C19 F1 106.89(16) . . ?
F2 C19 F3 105.58(15) . . ?
F1 C19 F3 105.05(15) . . ?
F2 C19 C11 113.07(14) . . ?
F1 C19 C11 113.19(15) . . ?
F3 C19 C11 112.41(15) . . ?
N1 C18 H18A 109.5 . . ?
N1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C11 C10 C9 120.00(17) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C8 C9 C10 120.63(16) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        26.47
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.039
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_Compd3fbi
_database_code_depnum_ccdc_archive 'CCDC 1857229'
loop_
_audit_author_name
_audit_author_address
'K C Kumara Swamy'
;University of Hyderabad
India
;
_audit_update_record             
;
2018-07-21 deposited with the CCDC.	2019-06-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H16 N2 O3 S2'
_chemical_formula_weight         384.46

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   7.507(4)
_cell_length_b                   16.207(10)
_cell_length_c                   29.663(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3609(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    7736
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      26.24

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1600
_exptl_absorpt_coefficient_mu    0.317
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            49959
_diffrn_reflns_av_R_equivalents  0.2687
_diffrn_reflns_av_sigmaI/netI    0.0681
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.61
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3166
_reflns_number_gt                2162
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. The quality of data was not 
 great and hence there are a couple of type A alerts.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1503P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.037(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3166
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1239
_refine_ls_R_factor_gt           0.0722
_refine_ls_wR_factor_ref         0.2270
_refine_ls_wR_factor_gt          0.1853
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.65283(17) 0.36297(6) 0.66434(3) 0.0479(4) Uani 1 1 d . . .
S2 S 0.61427(19) 0.54487(7) 0.62415(4) 0.0595(5) Uani 1 1 d . . .
O3 O 0.7562(4) 0.74646(15) 0.44595(9) 0.0505(8) Uani 1 1 d . . .
O1 O 0.4777(5) 0.35160(19) 0.64625(10) 0.0631(9) Uani 1 1 d . . .
O2 O 0.7389(5) 0.29517(18) 0.68549(10) 0.0675(10) Uani 1 1 d . . .
N1 N 0.7911(5) 0.3966(2) 0.62469(11) 0.0500(10) Uani 1 1 d . . .
N2 N 0.8040(6) 0.4728(2) 0.55877(11) 0.0532(10) Uani 1 1 d . . .
C18 C 0.8293(7) 0.8236(2) 0.45928(16) 0.0590(13) Uani 1 1 d . . .
H18A H 0.7793 0.8398 0.4877 0.088 Uiso 1 1 calc R . .
H18B H 0.8019 0.8646 0.4370 0.088 Uiso 1 1 calc R . .
H18C H 0.9563 0.8186 0.4622 0.088 Uiso 1 1 calc R . .
C14 C 0.8524(6) 0.6888(2) 0.51744(14) 0.0480(11) Uani 1 1 d . . .
H14 H 0.9029 0.7384 0.5267 0.058 Uiso 1 1 calc R . .
C15 C 0.7701(6) 0.6835(2) 0.47640(12) 0.0410(10) Uani 1 1 d . . .
C16 C 0.6957(6) 0.6090(2) 0.46286(13) 0.0474(11) Uani 1 1 d . . .
H16 H 0.6384 0.6050 0.4351 0.057 Uiso 1 1 calc R . .
C19 C 0.9161(8) 0.3377(3) 0.60442(16) 0.0672(15) Uani 1 1 d . . .
H19A H 0.8534 0.3028 0.5836 0.101 Uiso 1 1 calc R . .
H19B H 0.9687 0.3045 0.6277 0.101 Uiso 1 1 calc R . .
H19C H 1.0078 0.3673 0.5887 0.101 Uiso 1 1 calc R . .
C13 C 0.8605(6) 0.6202(3) 0.54523(14) 0.0529(12) Uani 1 1 d . . .
H13 H 0.9159 0.6248 0.5732 0.063 Uiso 1 1 calc R . .
C2 C 0.6504(6) 0.5036(3) 0.77665(14) 0.0463(10) Uani 1 1 d . . .
C12 C 0.7888(6) 0.5457(2) 0.53266(13) 0.0451(10) Uani 1 1 d . . .
C5 C 0.6319(6) 0.5278(2) 0.68221(15) 0.0482(11) Uani 1 1 d . . .
C11 C 0.7486(6) 0.4676(2) 0.59878(14) 0.0474(11) Uani 1 1 d . . .
C17 C 0.7069(7) 0.5417(2) 0.49047(13) 0.0515(12) Uani 1 1 d . . .
H17 H 0.6587 0.4918 0.4809 0.062 Uiso 1 1 calc R . .
C4 C 0.6245(7) 0.5948(3) 0.71107(15) 0.0553(12) Uani 1 1 d . . .
H4 H 0.6153 0.6478 0.6994 0.066 Uiso 1 1 calc R . .
C3 C 0.6310(7) 0.5827(3) 0.75796(14) 0.0517(11) Uani 1 1 d . . .
C6 C 0.6507(6) 0.4477(2) 0.70128(13) 0.0446(10) Uani 1 1 d . . .
C1 C 0.6631(6) 0.4353(3) 0.74622(14) 0.0496(11) Uani 1 1 d . . .
H1 H 0.6799 0.3823 0.7574 0.059 Uiso 1 1 calc R . .
C10 C 0.6207(8) 0.6513(3) 0.78920(18) 0.0693(15) Uani 1 1 d . . .
H10 H 0.6095 0.7047 0.7782 0.083 Uiso 1 1 calc R . .
C7 C 0.6586(7) 0.4928(3) 0.82360(16) 0.0621(13) Uani 1 1 d . . .
H7 H 0.6725 0.4402 0.8355 0.075 Uiso 1 1 calc R . .
C8 C 0.6463(8) 0.5584(3) 0.85152(17) 0.0690(14) Uani 1 1 d . . .
H8 H 0.6507 0.5507 0.8826 0.083 Uiso 1 1 calc R . .
C9 C 0.6269(9) 0.6387(4) 0.83358(19) 0.0799(18) Uani 1 1 d . . .
H9 H 0.6183 0.6835 0.8531 0.096 Uiso 1 1 calc R . .


_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 1.421(3) . ?
S1 O1 1.432(4) . ?
S1 N1 1.661(4) . ?
S1 C6 1.757(4) . ?
S2 C5 1.750(5) . ?
S2 C11 1.776(4) . ?
O3 C15 1.367(4) . ?
O3 C18 1.422(5) . ?
N1 C11 1.419(5) . ?
N1 C19 1.467(6) . ?
N2 C11 1.260(5) . ?
N2 C12 1.417(5) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C14 C15 1.368(6) . ?
C14 C13 1.386(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.389(5) . ?
C16 C17 1.367(6) . ?
C16 H16 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C13 C12 1.374(6) . ?
C13 H13 0.9300 . ?
C2 C7 1.405(6) . ?
C2 C3 1.406(6) . ?
C2 C1 1.430(6) . ?
C12 C17 1.396(6) . ?
C5 C4 1.383(6) . ?
C5 C6 1.423(6) . ?
C17 H17 0.9300 . ?
C4 C3 1.405(6) . ?
C4 H4 0.9300 . ?
C3 C10 1.449(6) . ?
C6 C1 1.351(6) . ?
C1 H1 0.9300 . ?
C10 C9 1.333(7) . ?
C10 H10 0.9300 . ?
C7 C8 1.350(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.414(8) . ?
C8 H8 0.9300 . ?
C9 H9 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
O2 S1 O1 118.9(2) . . ?
O2 S1 N1 106.4(2) . . ?
O1 S1 N1 110.5(2) . . ?
O2 S1 C6 109.5(2) . . ?
O1 S1 C6 109.0(2) . . ?
N1 S1 C6 101.00(19) . . ?
C5 S2 C11 105.2(2) . . ?
C15 O3 C18 116.3(3) . . ?
C11 N1 C19 116.7(3) . . ?
C11 N1 S1 120.6(3) . . ?
C19 N1 S1 118.4(3) . . ?
C11 N2 C12 123.0(4) . . ?
O3 C18 H18A 109.5 . . ?
O3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C15 C14 C13 119.9(4) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
O3 C15 C14 125.1(3) . . ?
O3 C15 C16 115.3(4) . . ?
C14 C15 C16 119.6(4) . . ?
C17 C16 C15 119.7(4) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
N1 C19 H19A 109.5 . . ?
N1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C12 C13 C14 121.8(4) . . ?
C12 C13 H13 119.1 . . ?
C14 C13 H13 119.1 . . ?
C7 C2 C3 120.6(4) . . ?
C7 C2 C1 121.8(4) . . ?
C3 C2 C1 117.6(4) . . ?
C13 C12 C17 117.2(4) . . ?
C13 C12 N2 123.6(4) . . ?
C17 C12 N2 119.1(4) . . ?
C4 C5 C6 118.3(4) . . ?
C4 C5 S2 118.8(3) . . ?
C6 C5 S2 122.9(3) . . ?
N2 C11 N1 119.4(4) . . ?
N2 C11 S2 122.6(3) . . ?
N1 C11 S2 118.0(3) . . ?
C16 C17 C12 121.8(4) . . ?
C16 C17 H17 119.1 . . ?
C12 C17 H17 119.1 . . ?
C5 C4 C3 120.2(4) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C3 C2 121.4(4) . . ?
C4 C3 C10 121.7(4) . . ?
C2 C3 C10 117.0(4) . . ?
C1 C6 C5 122.3(4) . . ?
C1 C6 S1 119.9(3) . . ?
C5 C6 S1 117.8(3) . . ?
C6 C1 C2 120.2(4) . . ?
C6 C1 H1 119.9 . . ?
C2 C1 H1 119.9 . . ?
C9 C10 C3 120.8(5) . . ?
C9 C10 H10 119.6 . . ?
C3 C10 H10 119.6 . . ?
C8 C7 C2 120.5(5) . . ?
C8 C7 H7 119.7 . . ?
C2 C7 H7 119.7 . . ?
C7 C8 C9 120.0(5) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C10 C9 C8 121.1(5) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.097
_refine_diff_density_min         -1.157
_refine_diff_density_rms         0.428
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_Compd5ad
_database_code_depnum_ccdc_archive 'CCDC 1857230'
loop_
_audit_author_name
_audit_author_address
'K C Kumara Swamy'
;University of Hyderabad
India
;
_audit_update_record             
;
2018-07-21 deposited with the CCDC.	2019-06-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H26 F2 N4 O6 S2'
_chemical_formula_weight         640.67

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   p_1_21/n_1

loop_
_symmetry_equiv_pos_as_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                   12.557(2)
_cell_length_b                   18.579(2)
_cell_length_c                   13.015(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.300(19)
_cell_angle_gamma                90.00
_cell_volume                     2942.2(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    843
_cell_measurement_theta_min      4.2040
_cell_measurement_theta_max      67.1080

_exptl_crystal_description       blocks
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1328
_exptl_absorpt_coefficient_mu    2.198
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.00672
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'CrysAlisPro, Oxford Diffraction Ltd.'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11082
_diffrn_reflns_av_R_equivalents  0.1712
_diffrn_reflns_av_sigmaI/netI    0.2636
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.24
_diffrn_reflns_theta_max         67.74
_reflns_number_total             4959
_reflns_number_gt                1755
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1278P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4959
_refine_ls_number_parameters     401
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2423
_refine_ls_R_factor_gt           0.1065
_refine_ls_wR_factor_ref         0.3647
_refine_ls_wR_factor_gt          0.2442
_refine_ls_goodness_of_fit_ref   0.955
_refine_ls_restrained_S_all      0.955
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.1428(2) 0.61267(11) 0.58185(18) 0.0442(6) Uani 1 1 d . . .
S2 S 0.5610(2) 0.88118(13) 0.5741(2) 0.0510(6) Uani 1 1 d . . .
O6 O 0.5437(8) 0.7840(4) 0.3218(5) 0.068(2) Uani 1 1 d . . .
F2 F 0.4760(7) 0.4656(4) 0.3196(6) 0.093(3) Uani 1 1 d . . .
O2 O 0.1854(6) 0.5511(3) 0.6457(7) 0.068(2) Uani 1 1 d . . .
O5 O 0.6142(7) 0.9469(4) 0.6147(7) 0.068(2) Uani 1 1 d . . .
N2 N 0.0337(5) 0.7533(4) 0.5762(6) 0.0404(16) Uani 1 1 d . . .
O3 O -0.1349(5) 0.6961(4) 0.5379(7) 0.069(2) Uani 1 1 d . . .
O1 O 0.1419(7) 0.6089(4) 0.4714(6) 0.065(2) Uani 1 1 d . . .
N4 N 0.5732(6) 0.7365(4) 0.4887(7) 0.051(2) Uani 1 1 d . . .
O4 O 0.4452(5) 0.8790(5) 0.5589(6) 0.067(2) Uani 1 1 d . . .
N1 N 0.0200(6) 0.6266(4) 0.5953(7) 0.0470(19) Uani 1 1 d . . .
N3 N 0.5940(6) 0.8618(4) 0.4620(6) 0.0452(18) Uani 1 1 d . . .
C6 C 0.1453(6) 0.7532(4) 0.6255(6) 0.0367(18) Uani 1 1 d . . .
F1 F -0.1739(6) 1.0137(4) 0.4588(7) 0.108(3) Uani 1 1 d . . .
C28 C 0.5659(8) 0.7921(5) 0.4171(7) 0.047(2) Uani 1 1 d . . .
C5 C 0.1958(7) 0.8169(4) 0.6689(7) 0.043(2) Uani 1 1 d . . .
H5 H 0.1549 0.8590 0.6646 0.052 Uiso 1 1 calc R . .
C4 C 0.3083(6) 0.8172(5) 0.7188(7) 0.041(2) Uani 1 1 d . . .
C16 C 0.6218(7) 0.8096(5) 0.6477(8) 0.047(2) Uani 1 1 d . . .
C21 C 0.6190(7) 0.7433(5) 0.5979(7) 0.0402(19) Uani 1 1 d . . .
C7 C -0.0237(7) 0.8223(4) 0.5465(7) 0.044(2) Uani 1 1 d . . .
C22 C 0.5478(7) 0.6666(5) 0.4421(7) 0.044(2) Uani 1 1 d . . .
C1 C 0.2043(7) 0.6903(5) 0.6380(7) 0.041(2) Uani 1 1 d . . .
C20 C 0.6583(8) 0.6810(6) 0.6581(8) 0.049(2) Uani 1 1 d . . .
H20 H 0.6553 0.6362 0.6257 0.059 Uiso 1 1 calc R . .
C23 C 0.4475(8) 0.6368(6) 0.4399(8) 0.055(3) Uani 1 1 d . . .
H23 H 0.3972 0.6624 0.4672 0.067 Uiso 1 1 calc R . .
C13 C -0.0336(7) 0.6925(5) 0.5686(8) 0.046(2) Uani 1 1 d . . .
C19 C 0.7026(8) 0.6884(6) 0.7693(8) 0.053(3) Uani 1 1 d . . .
C2 C 0.3180(7) 0.6900(5) 0.6890(9) 0.058(3) Uani 1 1 d . . .
H2 H 0.3586 0.6476 0.6966 0.069 Uiso 1 1 calc R . .
C27 C 0.6241(8) 0.6295(6) 0.4032(9) 0.057(3) Uani 1 1 d . . .
H27 H 0.6918 0.6503 0.4043 0.068 Uiso 1 1 calc R . .
C15 C -0.0528(9) 0.5639(6) 0.5950(9) 0.063(3) Uani 1 1 d . . .
H15A H -0.1044 0.5749 0.6362 0.095 Uiso 1 1 calc R . .
H15B H -0.0094 0.5231 0.6251 0.095 Uiso 1 1 calc R . .
H15C H -0.0918 0.5532 0.5234 0.095 Uiso 1 1 calc R . .
C17 C 0.6651(8) 0.8141(5) 0.7563(8) 0.053(2) Uani 1 1 d . . .
H17 H 0.6685 0.8589 0.7889 0.063 Uiso 1 1 calc R . .
C3 C 0.3666(8) 0.7543(5) 0.7267(9) 0.056(3) Uani 1 1 d . . .
H3 H 0.4415 0.7550 0.7588 0.067 Uiso 1 1 calc R . .
C8 C -0.0121(9) 0.8545(5) 0.4545(9) 0.060(3) Uani 1 1 d . . .
H8 H 0.0295 0.8335 0.4126 0.072 Uiso 1 1 calc R . .
C12 C -0.0827(8) 0.8524(6) 0.6108(9) 0.061(3) Uani 1 1 d . . .
H12 H -0.0878 0.8296 0.6731 0.073 Uiso 1 1 calc R . .
C14 C 0.3615(8) 0.8855(6) 0.7692(9) 0.060(3) Uani 1 1 d . . .
H14A H 0.3412 0.8937 0.8346 0.089 Uiso 1 1 calc R . .
H14B H 0.3374 0.9252 0.7221 0.089 Uiso 1 1 calc R . .
H14C H 0.4400 0.8810 0.7830 0.089 Uiso 1 1 calc R . .
C25 C 0.4986(9) 0.5325(6) 0.3599(8) 0.056(3) Uani 1 1 d . . .
C26 C 0.5994(8) 0.5613(6) 0.3624(8) 0.055(3) Uani 1 1 d . . .
H26 H 0.6507 0.5353 0.3369 0.066 Uiso 1 1 calc R . .
C11 C -0.1350(8) 0.9178(6) 0.5811(12) 0.071(4) Uani 1 1 d . . .
H11 H -0.1755 0.9401 0.6230 0.085 Uiso 1 1 calc R . .
C9 C -0.0650(10) 0.9196(6) 0.4275(9) 0.067(3) Uani 1 1 d . . .
H9 H -0.0586 0.9434 0.3665 0.080 Uiso 1 1 calc R . .
C18 C 0.7024(9) 0.7561(7) 0.8165(8) 0.066(3) Uani 1 1 d . . .
H18 H 0.7281 0.7609 0.8895 0.080 Uiso 1 1 calc R . .
C10 C -0.1250(10) 0.9485(6) 0.4879(11) 0.072(4) Uani 1 1 d . . .
C30 C 0.5900(10) 0.9237(6) 0.3868(8) 0.062(3) Uani 1 1 d . . .
H30A H 0.6363 0.9134 0.3400 0.092 Uiso 1 1 calc R . .
H30B H 0.6153 0.9666 0.4263 0.092 Uiso 1 1 calc R . .
H30C H 0.5158 0.9305 0.3461 0.092 Uiso 1 1 calc R . .
C24 C 0.4202(8) 0.5690(7) 0.3976(10) 0.068(3) Uani 1 1 d . . .
H24 H 0.3518 0.5488 0.3947 0.082 Uiso 1 1 calc R . .
C29 C 0.7457(10) 0.6200(7) 0.8302(10) 0.083(4) Uani 1 1 d . . .
H29A H 0.8195 0.6110 0.8251 0.125 Uiso 1 1 calc R . .
H29B H 0.6997 0.5801 0.8005 0.125 Uiso 1 1 calc R . .
H29C H 0.7450 0.6258 0.9033 0.125 Uiso 1 1 calc R . .


_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 1.437(8) . ?
S1 O2 1.437(7) . ?
S1 N1 1.615(8) . ?
S1 C1 1.713(9) . ?
S2 O4 1.419(7) . ?
S2 O5 1.428(7) . ?
S2 N3 1.653(8) . ?
S2 C16 1.705(9) . ?
O6 C28 1.212(11) . ?
F2 C25 1.352(11) . ?
N2 C6 1.390(9) . ?
N2 C13 1.400(10) . ?
N2 C7 1.474(10) . ?
O3 C13 1.237(11) . ?
N4 C28 1.379(12) . ?
N4 C21 1.401(11) . ?
N4 C22 1.435(11) . ?
N1 C13 1.398(11) . ?
N1 C15 1.479(11) . ?
N3 C28 1.429(11) . ?
N3 C30 1.502(12) . ?
C6 C1 1.372(11) . ?
C6 C5 1.393(10) . ?
F1 C10 1.368(12) . ?
C5 C4 1.402(11) . ?
C5 H5 0.9300 . ?
C4 C3 1.370(13) . ?
C4 C14 1.506(12) . ?
C16 C17 1.387(12) . ?
C16 C21 1.388(13) . ?
C21 C20 1.417(12) . ?
C7 C12 1.368(15) . ?
C7 C8 1.377(14) . ?
C22 C23 1.370(13) . ?
C22 C27 1.374(14) . ?
C1 C2 1.418(12) . ?
C20 C19 1.422(12) . ?
C20 H20 0.9300 . ?
C23 C24 1.383(16) . ?
C23 H23 0.9300 . ?
C19 C18 1.399(16) . ?
C19 C29 1.525(13) . ?
C2 C3 1.375(14) . ?
C2 H2 0.9300 . ?
C27 C26 1.379(14) . ?
C27 H27 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C17 C18 1.348(15) . ?
C17 H17 0.9300 . ?
C3 H3 0.9300 . ?
C8 C9 1.383(14) . ?
C8 H8 0.9300 . ?
C12 C11 1.390(14) . ?
C12 H12 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C25 C26 1.368(15) . ?
C25 C24 1.381(16) . ?
C26 H26 0.9300 . ?
C11 C10 1.374(18) . ?
C11 H11 0.9300 . ?
C9 C10 1.328(18) . ?
C9 H9 0.9300 . ?
C18 H18 0.9300 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C24 H24 0.9300 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 116.7(5) . . ?
O1 S1 N1 110.2(5) . . ?
O2 S1 N1 107.1(5) . . ?
O1 S1 C1 111.0(5) . . ?
O2 S1 C1 111.0(4) . . ?
N1 S1 C1 99.2(4) . . ?
O4 S2 O5 116.5(5) . . ?
O4 S2 N3 110.0(4) . . ?
O5 S2 N3 108.4(5) . . ?
O4 S2 C16 110.9(5) . . ?
O5 S2 C16 110.8(5) . . ?
N3 S2 C16 98.7(5) . . ?
C6 N2 C13 123.6(7) . . ?
C6 N2 C7 119.6(6) . . ?
C13 N2 C7 115.9(7) . . ?
C28 N4 C21 124.0(8) . . ?
C28 N4 C22 115.0(8) . . ?
C21 N4 C22 120.2(8) . . ?
C13 N1 C15 115.4(8) . . ?
C13 N1 S1 121.8(7) . . ?
C15 N1 S1 118.6(7) . . ?
C28 N3 C30 117.5(8) . . ?
C28 N3 S2 117.9(7) . . ?
C30 N3 S2 115.7(7) . . ?
C1 C6 N2 120.6(7) . . ?
C1 C6 C5 119.8(7) . . ?
N2 C6 C5 119.5(7) . . ?
O6 C28 N4 124.0(9) . . ?
O6 C28 N3 120.1(9) . . ?
N4 C28 N3 115.8(8) . . ?
C6 C5 C4 119.8(8) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C3 C4 C5 119.3(8) . . ?
C3 C4 C14 121.0(8) . . ?
C5 C4 C14 119.6(8) . . ?
C17 C16 C21 119.3(9) . . ?
C17 C16 S2 122.2(8) . . ?
C21 C16 S2 118.3(7) . . ?
C16 C21 N4 120.7(8) . . ?
C16 C21 C20 120.1(9) . . ?
N4 C21 C20 119.1(8) . . ?
C12 C7 C8 123.0(9) . . ?
C12 C7 N2 119.8(9) . . ?
C8 C7 N2 117.2(9) . . ?
C23 C22 C27 120.7(9) . . ?
C23 C22 N4 118.8(10) . . ?
C27 C22 N4 120.4(9) . . ?
C6 C1 C2 120.7(8) . . ?
C6 C1 S1 119.6(6) . . ?
C2 C1 S1 119.5(7) . . ?
C21 C20 C19 118.6(10) . . ?
C21 C20 H20 120.7 . . ?
C19 C20 H20 120.7 . . ?
C22 C23 C24 120.8(11) . . ?
C22 C23 H23 119.6 . . ?
C24 C23 H23 119.6 . . ?
O3 C13 N1 121.4(8) . . ?
O3 C13 N2 122.2(9) . . ?
N1 C13 N2 116.3(8) . . ?
C18 C19 C20 119.5(9) . . ?
C18 C19 C29 124.0(10) . . ?
C20 C19 C29 116.5(10) . . ?
C3 C2 C1 118.0(9) . . ?
C3 C2 H2 121.0 . . ?
C1 C2 H2 121.0 . . ?
C22 C27 C26 119.4(10) . . ?
C22 C27 H27 120.3 . . ?
C26 C27 H27 120.3 . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C18 C17 C16 122.4(10) . . ?
C18 C17 H17 118.8 . . ?
C16 C17 H17 118.8 . . ?
C4 C3 C2 122.2(8) . . ?
C4 C3 H3 118.9 . . ?
C2 C3 H3 118.9 . . ?
C7 C8 C9 117.0(11) . . ?
C7 C8 H8 121.5 . . ?
C9 C8 H8 121.5 . . ?
C7 C12 C11 118.4(12) . . ?
C7 C12 H12 120.8 . . ?
C11 C12 H12 120.8 . . ?
C4 C14 H14A 109.5 . . ?
C4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
F2 C25 C26 118.3(11) . . ?
F2 C25 C24 119.3(11) . . ?
C26 C25 C24 122.4(10) . . ?
C25 C26 C27 119.2(10) . . ?
C25 C26 H26 120.4 . . ?
C27 C26 H26 120.4 . . ?
C10 C11 C12 118.0(11) . . ?
C10 C11 H11 121.0 . . ?
C12 C11 H11 121.0 . . ?
C10 C9 C8 120.7(12) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C17 C18 C19 120.1(9) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C9 C10 F1 118.4(14) . . ?
C9 C10 C11 122.9(10) . . ?
F1 C10 C11 118.6(13) . . ?
N3 C30 H30A 109.5 . . ?
N3 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
N3 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C25 C24 C23 117.4(10) . . ?
C25 C24 H24 121.3 . . ?
C23 C24 H24 121.3 . . ?
C19 C29 H29A 109.5 . . ?
C19 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C19 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.931
_diffrn_reflns_theta_full        67.74
_diffrn_measured_fraction_theta_full 0.930
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.700
_refine_diff_density_rms         0.110
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
