# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_Compound4
_database_code_depnum_ccdc_archive 'CCDC 1885280'
loop_
_audit_author_name
_audit_author_address
'K C Kumara Swamy'
;University of Hyderabad
India
;
_audit_update_record             
;
2018-12-15 deposited with the CCDC.	2019-02-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H16 Br2 F N O3 S'
_chemical_formula_weight         505.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.9921(3)
_cell_length_b                   11.2113(6)
_cell_length_c                   12.4434(7)
_cell_angle_alpha                96.443(2)
_cell_angle_beta                 95.376(2)
_cell_angle_gamma                95.626(2)
_cell_volume                     959.19(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9872
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      26.37

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.749
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             500
_exptl_absorpt_coefficient_mu    4.361
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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            37199
_diffrn_reflns_av_R_equivalents  0.0610
_diffrn_reflns_av_sigmaI/netI    0.0291
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.32
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3377
_reflns_number_gt                2936
_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. 
;

_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)+(0.1196P)²+1.4748P] 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       0.034(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3377
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0479
_refine_ls_wR_factor_ref         0.1485
_refine_ls_wR_factor_gt          0.1414
_refine_ls_goodness_of_fit_ref   0.897
_refine_ls_restrained_S_all      0.897
_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
Br2 Br 0.11566(6) 0.47930(4) 0.17839(4) 0.0474(2) Uani 1 1 d . . .
Br1 Br 0.96206(11) 0.91991(6) 0.13275(7) 0.0811(3) Uani 1 1 d . . .
S1 S 0.37228(16) 0.73115(10) 0.39075(9) 0.0401(3) Uani 1 1 d . . .
O3 O 0.6869(4) 0.6130(2) 0.2230(3) 0.0388(7) Uani 1 1 d . . .
O2 O 0.2622(5) 0.6237(3) 0.4097(3) 0.0533(8) Uani 1 1 d . . .
O1 O 0.2931(5) 0.8435(3) 0.4003(3) 0.0570(9) Uani 1 1 d . . .
N1 N 0.4240(5) 0.7094(3) 0.2601(3) 0.0362(8) Uani 1 1 d . . .
F1 F 0.4163(7) 0.0630(3) 0.1665(4) 0.0904(12) Uani 1 1 d . . .
C11 C 0.4919(6) 0.5982(3) 0.2239(3) 0.0316(8) Uani 1 1 d . . .
C12 C 0.3898(5) 0.4931(4) 0.1876(3) 0.0324(8) Uani 1 1 d . . .
C13 C 0.4714(5) 0.3819(3) 0.1475(3) 0.0309(8) Uani 1 1 d . . .
C1 C 0.5942(7) 0.7475(4) 0.4719(3) 0.0390(9) Uani 1 1 d . . .
C14 C 0.6149(6) 0.3855(4) 0.0775(3) 0.0395(9) Uani 1 1 d . . .
H14 H 0.6632 0.4590 0.0573 0.047 Uiso 1 1 calc R . .
C6 C 0.6841(7) 0.6454(4) 0.4904(4) 0.0452(10) Uani 1 1 d . . .
H6 H 0.6244 0.5689 0.4626 0.054 Uiso 1 1 calc R . .
C9 C 0.7555(7) 0.7394(4) 0.2299(4) 0.0451(10) Uani 1 1 d . . .
H9 H 0.8420 0.7656 0.2968 0.054 Uiso 1 1 calc R . .
C8 C 0.5688(7) 0.8024(4) 0.2312(4) 0.0405(10) Uani 1 1 d . . .
H8A H 0.5860 0.8734 0.2849 0.049 Uiso 1 1 calc R . .
H8B H 0.5307 0.8262 0.1604 0.049 Uiso 1 1 calc R . .
C2 C 0.6837(8) 0.8613(4) 0.5141(4) 0.0523(12) Uani 1 1 d . . .
H2 H 0.6244 0.9298 0.5014 0.063 Uiso 1 1 calc R . .
C18 C 0.4027(7) 0.2708(4) 0.1770(4) 0.0443(10) Uani 1 1 d . . .
H18 H 0.3068 0.2655 0.2238 0.053 Uiso 1 1 calc R . .
C5 C 0.8623(8) 0.6586(5) 0.5502(4) 0.0515(12) Uani 1 1 d . . .
H5 H 0.9231 0.5905 0.5624 0.062 Uiso 1 1 calc R . .
C16 C 0.6192(7) 0.1713(4) 0.0665(4) 0.0514(12) Uani 1 1 d . . .
H16 H 0.6678 0.1009 0.0396 0.062 Uiso 1 1 calc R . .
C17 C 0.4784(8) 0.1692(4) 0.1358(4) 0.0501(12) Uani 1 1 d . . .
C15 C 0.6858(7) 0.2815(4) 0.0382(4) 0.0496(11) Uani 1 1 d . . .
H15 H 0.7814 0.2856 -0.0089 0.060 Uiso 1 1 calc R . .
C4 C 0.9520(7) 0.7716(5) 0.5925(4) 0.0521(12) Uani 1 1 d . . .
C3 C 0.8595(9) 0.8719(5) 0.5743(4) 0.0581(13) Uani 1 1 d . . .
H3 H 0.9181 0.9481 0.6037 0.070 Uiso 1 1 calc R . .
C10 C 0.8595(9) 0.7537(5) 0.1321(5) 0.0587(13) Uani 1 1 d . . .
H10A H 0.7713 0.7281 0.0668 0.070 Uiso 1 1 calc R . .
H10B H 0.9641 0.7030 0.1315 0.070 Uiso 1 1 calc R . .
C7 C 1.1473(9) 0.7848(7) 0.6601(5) 0.0799(19) Uani 1 1 d . . .
H7A H 1.1313 0.8081 0.7351 0.120 Uiso 1 1 calc R . .
H7B H 1.2326 0.8456 0.6349 0.120 Uiso 1 1 calc R . .
H7C H 1.2013 0.7092 0.6530 0.120 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
Br2 C12 1.899(4) . ?
Br1 C10 1.928(5) . ?
S1 O1 1.422(3) . ?
S1 O2 1.419(3) . ?
S1 N1 1.694(4) . ?
S1 C1 1.752(5) . ?
O3 C11 1.358(5) . ?
O3 C9 1.441(5) . ?
N1 C11 1.419(5) . ?
N1 C8 1.479(6) . ?
F1 C17 1.335(6) . ?
C11 C12 1.326(6) . ?
C12 C13 1.477(5) . ?
C13 C18 1.391(6) . ?
C13 C14 1.389(6) . ?
C1 C2 1.388(6) . ?
C1 C6 1.389(6) . ?
C14 C15 1.370(6) . ?
C14 H14 0.9300 . ?
C6 C5 1.376(7) . ?
C6 H6 0.9300 . ?
C9 C10 1.491(7) . ?
C9 C8 1.545(6) . ?
C9 H9 0.9800 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C2 C3 1.366(8) . ?
C2 H2 0.9300 . ?
C18 C17 1.371(6) . ?
C18 H18 0.9300 . ?
C5 C4 1.381(8) . ?
C5 H5 0.9300 . ?
C16 C15 1.372(7) . ?
C16 C17 1.369(8) . ?
C16 H16 0.9300 . ?
C15 H15 0.9300 . ?
C4 C3 1.381(8) . ?
C4 C7 1.520(8) . ?
C3 H3 0.9300 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 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 120.7(2) . . ?
O1 S1 N1 104.8(2) . . ?
O2 S1 N1 106.47(19) . . ?
O1 S1 C1 108.7(2) . . ?
O2 S1 C1 109.0(2) . . ?
N1 S1 C1 106.24(19) . . ?
C11 O3 C9 110.4(3) . . ?
C11 N1 C8 104.4(3) . . ?
C11 N1 S1 117.5(3) . . ?
C8 N1 S1 114.3(3) . . ?
C12 C11 O3 121.1(3) . . ?
C12 C11 N1 128.4(4) . . ?
O3 C11 N1 110.3(3) . . ?
C11 C12 C13 125.1(4) . . ?
C11 C12 Br2 120.0(3) . . ?
C13 C12 Br2 114.8(3) . . ?
C18 C13 C14 118.6(4) . . ?
C18 C13 C12 120.6(4) . . ?
C14 C13 C12 120.8(4) . . ?
C2 C1 C6 120.0(4) . . ?
C2 C1 S1 120.6(4) . . ?
C6 C1 S1 119.4(3) . . ?
C15 C14 C13 120.4(4) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C5 C6 C1 119.3(4) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
O3 C9 C10 106.3(4) . . ?
O3 C9 C8 103.6(3) . . ?
C10 C9 C8 114.0(4) . . ?
O3 C9 H9 110.8 . . ?
C10 C9 H9 110.8 . . ?
C8 C9 H9 110.8 . . ?
N1 C8 C9 103.8(3) . . ?
N1 C8 H8A 111.0 . . ?
C9 C8 H8A 111.0 . . ?
N1 C8 H8B 111.0 . . ?
C9 C8 H8B 111.0 . . ?
H8A C8 H8B 109.0 . . ?
C3 C2 C1 119.5(5) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C17 C18 C13 118.9(4) . . ?
C17 C18 H18 120.5 . . ?
C13 C18 H18 120.5 . . ?
C6 C5 C4 120.9(5) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C15 C16 C17 117.3(4) . . ?
C15 C16 H16 121.4 . . ?
C17 C16 H16 121.4 . . ?
F1 C17 C16 117.9(4) . . ?
F1 C17 C18 118.9(5) . . ?
C16 C17 C18 123.2(4) . . ?
C16 C15 C14 121.6(5) . . ?
C16 C15 H15 119.2 . . ?
C14 C15 H15 119.2 . . ?
C5 C4 C3 118.9(5) . . ?
C5 C4 C7 120.5(5) . . ?
C3 C4 C7 120.6(5) . . ?
C2 C3 C4 121.3(5) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C9 C10 Br1 110.4(4) . . ?
C9 C10 H10A 109.6 . . ?
Br1 C10 H10A 109.6 . . ?
C9 C10 H10B 109.6 . . ?
Br1 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.947
_refine_diff_density_min         -1.082
_refine_diff_density_rms         0.133
_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_compound18
_database_code_depnum_ccdc_archive 'CCDC 1885282'
loop_
_audit_author_name
_audit_author_address
'K C Kumara Swamy'
;University of Hyderabad
India
;
_audit_update_record             
;
2018-12-15 deposited with the CCDC.	2019-02-21 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 H20 Cl N O3 S'
_chemical_formula_weight         377.87

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   18.258(2)
_cell_length_b                   13.0810(13)
_cell_length_c                   15.4466(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.845(3)
_cell_angle_gamma                90.00
_cell_volume                     3687.2(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    9411
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      26.35

_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    1.361
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1584
_exptl_absorpt_coefficient_mu    0.338
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      300(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            35242
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_sigmaI/netI    0.0124
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.23
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3227
_reflns_number_gt                2885
_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)+(0.0820P)²+3.1786P] 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       0.028(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3227
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0488
_refine_ls_wR_factor_ref         0.1434
_refine_ls_wR_factor_gt          0.1390
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_restrained_S_all      1.123
_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 0.12518(3) 0.60832(4) 0.54112(4) 0.0420(2) Uani 1 1 d . . .
Cl1 Cl 0.11174(5) 0.27750(6) 0.28908(5) 0.0818(3) Uani 1 1 d . . .
O3 O 0.23927(8) 0.38163(11) 0.40002(11) 0.0474(4) Uani 1 1 d . . .
O2 O 0.16915(9) 0.69624(12) 0.55955(12) 0.0537(4) Uani 1 1 d . . .
O1 O 0.04791(9) 0.61845(13) 0.52438(13) 0.0576(5) Uani 1 1 d . . .
N1 N 0.15906(9) 0.55646(13) 0.45315(12) 0.0407(4) Uani 1 1 d . . .
C13 C 0.35150(11) 0.47388(15) 0.40104(13) 0.0375(5) Uani 1 1 d . . .
C12 C 0.23645(11) 0.55452(15) 0.44735(13) 0.0378(5) Uani 1 1 d . . .
H12 H 0.2630 0.6119 0.4650 0.045 Uiso 1 1 calc R . .
C11 C 0.27266(11) 0.47402(15) 0.41777(13) 0.0372(5) Uani 1 1 d . . .
C1 C 0.14012(11) 0.51667(16) 0.62249(14) 0.0398(5) Uani 1 1 d . . .
C6 C 0.21037(12) 0.50414(18) 0.65826(14) 0.0445(5) Uani 1 1 d . . .
H6 H 0.2471 0.5506 0.6457 0.053 Uiso 1 1 calc R . .
C5 C 0.22542(13) 0.42255(19) 0.71241(15) 0.0496(6) Uani 1 1 d . . .
H5 H 0.2726 0.4142 0.7357 0.059 Uiso 1 1 calc R . .
C9 C 0.16806(12) 0.37159(17) 0.43588(15) 0.0446(5) Uani 1 1 d . . .
H9 H 0.1743 0.3654 0.4989 0.053 Uiso 1 1 calc R . .
C18 C 0.38891(12) 0.56456(17) 0.38537(15) 0.0457(5) Uani 1 1 d . . .
H18 H 0.3633 0.6260 0.3827 0.055 Uiso 1 1 calc R . .
C14 C 0.39165(13) 0.38356(17) 0.40277(16) 0.0467(5) Uani 1 1 d . . .
H14 H 0.3679 0.3217 0.4114 0.056 Uiso 1 1 calc R . .
C4 C 0.17160(13) 0.35261(18) 0.73284(15) 0.0491(6) Uani 1 1 d . . .
C2 C 0.08492(12) 0.44826(19) 0.64306(17) 0.0512(6) Uani 1 1 d . . .
H2 H 0.0376 0.4565 0.6200 0.061 Uiso 1 1 calc R . .
C8 C 0.12276(12) 0.46529(17) 0.41633(15) 0.0456(5) Uani 1 1 d . . .
H8A H 0.1162 0.4732 0.3541 0.055 Uiso 1 1 calc R . .
H8B H 0.0748 0.4576 0.4407 0.055 Uiso 1 1 calc R . .
C16 C 0.50404(12) 0.47453(19) 0.37754(15) 0.0482(6) Uani 1 1 d . . .
C3 C 0.10138(14) 0.36852(19) 0.69786(17) 0.0543(6) Uani 1 1 d . . .
H3 H 0.0643 0.3234 0.7122 0.065 Uiso 1 1 calc R . .
C17 C 0.46356(12) 0.56408(19) 0.37383(17) 0.0526(6) Uani 1 1 d . . .
H17 H 0.4873 0.6255 0.3633 0.063 Uiso 1 1 calc R . .
C10 C 0.13447(15) 0.27339(19) 0.40128(17) 0.0569(6) Uani 1 1 d . . .
H10A H 0.0905 0.2588 0.4326 0.068 Uiso 1 1 calc R . .
H10B H 0.1687 0.2178 0.4122 0.068 Uiso 1 1 calc R . .
C15 C 0.46652(13) 0.38470(19) 0.39180(17) 0.0538(6) Uani 1 1 d . . .
H15 H 0.4923 0.3234 0.3941 0.065 Uiso 1 1 calc R . .
C7 C 0.18875(19) 0.2620(2) 0.78919(19) 0.0686(8) Uani 1 1 d . . .
H7A H 0.2365 0.2703 0.8162 0.103 Uiso 1 1 calc R . .
H7B H 0.1879 0.2011 0.7545 0.103 Uiso 1 1 calc R . .
H7C H 0.1528 0.2567 0.8330 0.103 Uiso 1 1 calc R . .
C19 C 0.58567(14) 0.4761(2) 0.3652(2) 0.0696(8) Uani 1 1 d . . .
H19A H 0.6088 0.4260 0.4023 0.104 Uiso 1 1 calc R . .
H19B H 0.6046 0.5426 0.3794 0.104 Uiso 1 1 calc R . .
H19C H 0.5955 0.4605 0.3059 0.104 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 1.4259(17) . ?
S1 O1 1.4322(17) . ?
S1 N1 1.6563(19) . ?
S1 C1 1.752(2) . ?
Cl1 C10 1.770(3) . ?
O3 C11 1.377(2) . ?
O3 C9 1.436(3) . ?
N1 C12 1.419(3) . ?
N1 C8 1.470(3) . ?
C13 C14 1.390(3) . ?
C13 C18 1.394(3) . ?
C13 C11 1.471(3) . ?
C12 C11 1.332(3) . ?
C12 H12 0.9300 . ?
C1 C6 1.390(3) . ?
C1 C2 1.392(3) . ?
C6 C5 1.378(3) . ?
C6 H6 0.9300 . ?
C5 C4 1.387(3) . ?
C5 H5 0.9300 . ?
C9 C8 1.504(3) . ?
C9 C10 1.514(3) . ?
C9 H9 0.9800 . ?
C18 C17 1.380(3) . ?
C18 H18 0.9300 . ?
C14 C15 1.383(3) . ?
C14 H14 0.9300 . ?
C4 C3 1.391(4) . ?
C4 C7 1.497(4) . ?
C2 C3 1.371(4) . ?
C2 H2 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C16 C15 1.381(3) . ?
C16 C17 1.385(3) . ?
C16 C19 1.509(3) . ?
C3 H3 0.9300 . ?
C17 H17 0.9300 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C15 H15 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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 120.42(10) . . ?
O2 S1 N1 105.75(10) . . ?
O1 S1 N1 106.35(10) . . ?
O2 S1 C1 109.58(11) . . ?
O1 S1 C1 108.81(10) . . ?
N1 S1 C1 104.75(9) . . ?
C11 O3 C9 113.83(16) . . ?
C12 N1 C8 113.49(17) . . ?
C12 N1 S1 117.26(14) . . ?
C8 N1 S1 118.30(14) . . ?
C14 C13 C18 117.7(2) . . ?
C14 C13 C11 121.08(18) . . ?
C18 C13 C11 121.15(18) . . ?
C11 C12 N1 122.82(18) . . ?
C11 C12 H12 118.6 . . ?
N1 C12 H12 118.6 . . ?
C12 C11 O3 122.73(18) . . ?
C12 C11 C13 124.10(18) . . ?
O3 C11 C13 113.17(17) . . ?
C6 C1 C2 119.9(2) . . ?
C6 C1 S1 119.10(16) . . ?
C2 C1 S1 120.43(17) . . ?
C5 C6 C1 119.7(2) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
C6 C5 C4 121.3(2) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
O3 C9 C8 110.30(18) . . ?
O3 C9 C10 107.65(18) . . ?
C8 C9 C10 114.01(19) . . ?
O3 C9 H9 108.2 . . ?
C8 C9 H9 108.2 . . ?
C10 C9 H9 108.2 . . ?
C17 C18 C13 120.7(2) . . ?
C17 C18 H18 119.7 . . ?
C13 C18 H18 119.7 . . ?
C15 C14 C13 120.7(2) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C5 C4 C3 117.7(2) . . ?
C5 C4 C7 121.2(2) . . ?
C3 C4 C7 121.1(2) . . ?
C3 C2 C1 119.0(2) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
N1 C8 C9 110.20(17) . . ?
N1 C8 H8A 109.6 . . ?
C9 C8 H8A 109.6 . . ?
N1 C8 H8B 109.6 . . ?
C9 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
C15 C16 C17 117.3(2) . . ?
C15 C16 C19 121.9(2) . . ?
C17 C16 C19 120.8(2) . . ?
C2 C3 C4 122.3(2) . . ?
C2 C3 H3 118.8 . . ?
C4 C3 H3 118.8 . . ?
C18 C17 C16 121.8(2) . . ?
C18 C17 H17 119.1 . . ?
C16 C17 H17 119.1 . . ?
C9 C10 Cl1 113.55(17) . . ?
C9 C10 H10A 108.9 . . ?
Cl1 C10 H10A 108.9 . . ?
C9 C10 H10B 108.9 . . ?
Cl1 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
C16 C15 C14 121.7(2) . . ?
C16 C15 H15 119.1 . . ?
C14 C15 H15 119.1 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.717
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.114
_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_compound28
_database_code_depnum_ccdc_archive 'CCDC 1885284'
loop_
_audit_author_name
_audit_author_address
'K C Kumara Swamy'
;University of Hyderabad
India
;
_audit_update_record             
;
2018-12-15 deposited with the CCDC.	2019-02-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H14 N2 O7 S'
_chemical_formula_weight         390.36

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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                   7.4466(5)
_cell_length_b                   24.7338(15)
_cell_length_c                   9.6421(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.560(2)
_cell_angle_gamma                90.00
_cell_volume                     1718.87(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    8794
_cell_measurement_theta_min      2.94
_cell_measurement_theta_max      24.80

_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    1.508
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    0.233
_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            35288
_diffrn_reflns_av_R_equivalents  0.0636
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.33
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3032
_reflns_number_gt                2348
_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. 
;

_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)+(0.0497P)²+1.0299P] 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         3032
_refine_ls_number_parameters     247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.1128
_refine_ls_wR_factor_gt          0.1037
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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 0.45682(8) 0.46323(2) 0.77401(6) 0.03822(18) Uani 1 1 d . . .
O1 O 0.5709(2) 0.44077(7) 0.90271(18) 0.0510(5) Uani 1 1 d . . .
O2 O 0.5191(2) 0.50880(7) 0.70918(19) 0.0512(5) Uani 1 1 d . . .
O6 O 0.0357(3) 0.54410(8) 0.8048(2) 0.0645(6) Uani 1 1 d . . .
O7 O 0.1576(3) 0.54113(7) 0.5141(2) 0.0640(6) Uani 1 1 d . . .
N1 N 0.2600(3) 0.48225(7) 0.8114(2) 0.0358(4) Uani 1 1 d . . .
N2 N 0.2098(3) 0.28563(9) 0.3528(3) 0.0570(6) Uani 1 1 d . . .
O3 O 0.0689(4) 0.36456(8) 0.8109(3) 0.0799(7) Uani 1 1 d . . .
O4 O 0.2238(4) 0.23951(8) 0.3960(3) 0.0888(8) Uani 1 1 d . . .
O5 O 0.1425(4) 0.29770(9) 0.2291(3) 0.0908(8) Uani 1 1 d . . .
C1 C 0.3935(3) 0.41038(9) 0.6483(2) 0.0349(5) Uani 1 1 d . . .
C4 C 0.2803(3) 0.32954(9) 0.4562(3) 0.0418(6) Uani 1 1 d . . .
C2 C 0.4169(4) 0.35718(10) 0.6941(3) 0.0453(6) Uani 1 1 d . . .
H2 H 0.4710 0.3492 0.7897 0.054 Uiso 1 1 calc R . .
C10 C 0.1624(3) 0.52896(9) 0.7578(3) 0.0419(6) Uani 1 1 d . . .
C6 C 0.3188(4) 0.42282(10) 0.5055(3) 0.0454(6) Uani 1 1 d . . .
H6 H 0.3073 0.4587 0.4754 0.055 Uiso 1 1 calc R . .
C5 C 0.2617(4) 0.38182(10) 0.4085(3) 0.0481(6) Uani 1 1 d . . .
H5 H 0.2111 0.3894 0.3121 0.058 Uiso 1 1 calc R . .
C11 C 0.1994(4) 0.56138(10) 0.6317(3) 0.0452(6) Uani 1 1 d . . .
C12 C 0.2564(4) 0.61836(9) 0.6591(3) 0.0440(6) Uani 1 1 d . . .
C7 C 0.1912(4) 0.45186(9) 0.9198(3) 0.0436(6) Uani 1 1 d . . .
H7A H 0.1556 0.4771 0.9850 0.052 Uiso 1 1 calc R . .
H7B H 0.2902 0.4293 0.9751 0.052 Uiso 1 1 calc R . .
C3 C 0.3595(4) 0.31627(10) 0.5968(3) 0.0483(6) Uani 1 1 d . . .
H3 H 0.3738 0.2803 0.6255 0.058 Uiso 1 1 calc R . .
C17 C 0.2248(4) 0.65406(11) 0.5445(3) 0.0569(7) Uani 1 1 d . . .
H17 H 0.1682 0.6422 0.4523 0.068 Uiso 1 1 calc R . .
C8 C 0.0273(4) 0.41682(11) 0.8519(3) 0.0573(7) Uani 1 1 d . . .
H8 H -0.083(4) 0.4346(12) 0.779(3) 0.069 Uiso 1 1 d . . .
C13 C 0.3420(4) 0.63636(11) 0.7953(3) 0.0583(7) Uani 1 1 d . . .
H13 H 0.3620 0.6127 0.8727 0.070 Uiso 1 1 calc R . .
C16 C 0.2788(5) 0.70775(12) 0.5692(4) 0.0733(10) Uani 1 1 d . . .
H16 H 0.2561 0.7321 0.4933 0.088 Uiso 1 1 calc R . .
C14 C 0.3977(5) 0.68969(13) 0.8158(4) 0.0773(10) Uani 1 1 d . . .
H14 H 0.4583 0.7016 0.9070 0.093 Uiso 1 1 calc R . .
C15 C 0.3647(5) 0.72491(12) 0.7036(5) 0.0791(11) Uani 1 1 d . . .
H15 H 0.4011 0.7608 0.7189 0.095 Uiso 1 1 calc R . .
C9 C -0.0169(5) 0.37079(12) 0.9271(4) 0.0738(9) Uani 1 1 d . . .
H9A H 0.0583 0.3642 1.0234 0.089 Uiso 1 1 calc R . .
H9B H -0.1465 0.3608 0.9109 0.089 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 1.4222(17) . ?
S1 O1 1.4284(18) . ?
S1 N1 1.663(2) . ?
S1 C1 1.764(2) . ?
O6 C10 1.204(3) . ?
O7 C11 1.206(3) . ?
N1 C10 1.393(3) . ?
N1 C7 1.479(3) . ?
N2 O5 1.209(3) . ?
N2 O4 1.210(3) . ?
N2 C4 1.479(3) . ?
O3 C8 1.409(3) . ?
O3 C9 1.431(4) . ?
C1 C6 1.384(3) . ?
C1 C2 1.385(3) . ?
C4 C5 1.368(3) . ?
C4 C3 1.375(3) . ?
C2 C3 1.373(3) . ?
C2 H2 0.9300 . ?
C10 C11 1.539(3) . ?
C6 C5 1.372(3) . ?
C6 H6 0.9300 . ?
C5 H5 0.9300 . ?
C11 C12 1.476(3) . ?
C12 C13 1.381(4) . ?
C12 C17 1.388(3) . ?
C7 C8 1.506(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C3 H3 0.9300 . ?
C17 C16 1.391(4) . ?
C17 H17 0.9300 . ?
C8 C9 1.432(4) . ?
C8 H8 1.04(3) . ?
C13 C14 1.382(4) . ?
C13 H13 0.9300 . ?
C16 C15 1.361(5) . ?
C16 H16 0.9300 . ?
C14 C15 1.362(5) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?

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 120.10(11) . . ?
O2 S1 N1 105.90(10) . . ?
O1 S1 N1 106.60(10) . . ?
O2 S1 C1 110.21(11) . . ?
O1 S1 C1 107.85(11) . . ?
N1 S1 C1 105.13(10) . . ?
C10 N1 C7 116.26(19) . . ?
C10 N1 S1 124.06(16) . . ?
C7 N1 S1 119.35(15) . . ?
O5 N2 O4 123.4(2) . . ?
O5 N2 C4 118.2(2) . . ?
O4 N2 C4 118.4(2) . . ?
C8 O3 C9 60.57(18) . . ?
C6 C1 C2 121.0(2) . . ?
C6 C1 S1 119.35(17) . . ?
C2 C1 S1 119.63(18) . . ?
C5 C4 C3 122.6(2) . . ?
C5 C4 N2 118.6(2) . . ?
C3 C4 N2 118.8(2) . . ?
C3 C2 C1 119.3(2) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
O6 C10 N1 120.2(2) . . ?
O6 C10 C11 116.6(2) . . ?
N1 C10 C11 123.0(2) . . ?
C5 C6 C1 119.5(2) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
C4 C5 C6 118.8(2) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
O7 C11 C12 124.0(2) . . ?
O7 C11 C10 118.1(2) . . ?
C12 C11 C10 117.1(2) . . ?
C13 C12 C17 119.8(2) . . ?
C13 C12 C11 121.4(2) . . ?
C17 C12 C11 118.8(2) . . ?
N1 C7 C8 111.8(2) . . ?
N1 C7 H7A 109.3 . . ?
C8 C7 H7A 109.3 . . ?
N1 C7 H7B 109.3 . . ?
C8 C7 H7B 109.3 . . ?
H7A C7 H7B 107.9 . . ?
C2 C3 C4 118.7(2) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C12 C17 C16 119.2(3) . . ?
C12 C17 H17 120.4 . . ?
C16 C17 H17 120.4 . . ?
O3 C8 C9 60.49(19) . . ?
O3 C8 C7 116.1(3) . . ?
C9 C8 C7 120.1(3) . . ?
O3 C8 H8 113.1(17) . . ?
C9 C8 H8 115.9(17) . . ?
C7 C8 H8 117.9(17) . . ?
C12 C13 C14 119.6(3) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C15 C16 C17 120.5(3) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C15 C14 C13 120.6(3) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C14 120.3(3) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
O3 C9 C8 58.93(19) . . ?
O3 C9 H9A 117.9 . . ?
C8 C9 H9A 117.9 . . ?
O3 C9 H9B 117.9 . . ?
C8 C9 H9B 117.9 . . ?
H9A C9 H9B 115.0 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.046
_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_compound21
_database_code_depnum_ccdc_archive 'CCDC 1885283'
loop_
_audit_author_name
_audit_author_address
'K C Kumara Swamy'
;University of Hyderabad
India
;
_audit_update_record             
;
2018-12-15 deposited with the CCDC.	2019-02-21 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 H25 N O4 S'
_chemical_formula_weight         387.48

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.994(13)
_cell_length_b                   12.052(15)
_cell_length_c                   16.90(2)
_cell_angle_alpha                95.131(11)
_cell_angle_beta                 99.760(11)
_cell_angle_gamma                103.107(11)
_cell_volume                     2130(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    1179
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      19.45

_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    1.208
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_absorpt_coefficient_mu    0.176
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(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            8145
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_sigmaI/netI    0.0929
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.23
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5863
_reflns_number_gt                2184
_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. 
;

_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)+(0.1824P)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         5863
_refine_ls_number_parameters     495
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.2175
_refine_ls_R_factor_gt           0.0973
_refine_ls_wR_factor_ref         0.3338
_refine_ls_wR_factor_gt          0.2554
_refine_ls_goodness_of_fit_ref   0.929
_refine_ls_restrained_S_all      0.933
_refine_ls_shift/su_max          0.189
_refine_ls_shift/su_mean         0.014

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 0.75117(17) 1.00847(16) 0.51915(14) 0.0815(7) Uani 1 1 d . . .
S1 S 0.6944(3) -0.0161(2) 0.16426(18) 0.1098(9) Uani 1 1 d . . .
O8 O 0.6765(4) 0.6555(4) 0.3957(3) 0.0888(16) Uani 1 1 d . . .
O5 O 0.6435(4) 1.0585(4) 0.5109(4) 0.0940(17) Uani 1 1 d . . .
O6 O 0.8738(4) 1.0765(4) 0.5093(4) 0.0957(18) Uani 1 1 d . . .
N2 N 0.7145(5) 0.8939(5) 0.4486(4) 0.0818(18) Uani 1 1 d . . .
O1 O 0.7731(6) -0.0680(6) 0.2180(5) 0.131(2) Uani 1 1 d . . .
O2 O 0.7101(6) -0.0075(5) 0.0814(4) 0.119(2) Uani 1 1 d . . .
C36 C 0.5783(6) 0.7005(6) 0.4167(4) 0.070(2) Uani 1 1 d . . .
C37 C 0.4557(7) 0.6106(6) 0.4054(4) 0.0655(19) Uani 1 1 d . . .
C35 C 0.5951(6) 0.8122(6) 0.4417(4) 0.066(2) Uani 1 1 d . . .
H35 H 0.5266 0.8378 0.4552 0.079 Uiso 1 1 calc R . .
O4 O 0.7011(7) 0.3345(6) 0.2805(5) 0.137(3) Uani 1 1 d . . .
O7 O 0.9212(6) 0.5966(6) 0.4330(5) 0.133(2) Uani 1 1 d . . .
H7 H 0.9889 0.6228 0.4650 0.199 Uiso 1 1 calc R . .
N1 N 0.7208(8) 0.1188(6) 0.2084(5) 0.114(3) Uani 1 1 d . . .
C22 C 0.7713(6) 0.9605(6) 0.6126(5) 0.077(2) Uani 1 1 d . . .
C23 C 0.6699(8) 0.9347(6) 0.6524(6) 0.088(2) Uani 1 1 d . . .
H23 H 0.5917 0.9467 0.6295 0.106 Uiso 1 1 calc R . .
C42 C 0.4546(8) 0.4947(7) 0.3946(5) 0.095(3) Uani 1 1 d . . .
H42 H 0.5298 0.4723 0.3926 0.114 Uiso 1 1 calc R . .
C24 C 0.6831(8) 0.8907(8) 0.7265(6) 0.104(3) Uani 1 1 d . . .
H24 H 0.6140 0.8788 0.7525 0.125 Uiso 1 1 calc R . .
C40 C 0.2301(10) 0.4389(9) 0.3890(5) 0.101(3) Uani 1 1 d . . .
H40 H 0.1553 0.3819 0.3841 0.121 Uiso 1 1 calc R . .
C1 C 0.5323(9) -0.0886(7) 0.1609(6) 0.090(2) Uani 1 1 d . . .
C27 C 0.8879(7) 0.9367(6) 0.6485(6) 0.092(3) Uani 1 1 d . . .
H27 H 0.9573 0.9505 0.6228 0.110 Uiso 1 1 calc R . .
C39 C 0.2271(8) 0.5527(8) 0.3985(6) 0.109(3) Uani 1 1 d . . .
H39 H 0.1503 0.5727 0.3990 0.131 Uiso 1 1 calc R . .
C38 C 0.3410(7) 0.6390(7) 0.4074(5) 0.091(3) Uani 1 1 d . . .
H38 H 0.3390 0.7159 0.4147 0.110 Uiso 1 1 calc R . .
C25 C 0.7956(9) 0.8635(7) 0.7640(6) 0.095(3) Uani 1 1 d . . .
C26 C 0.8977(8) 0.8926(7) 0.7224(7) 0.103(3) Uani 1 1 d . . .
H26 H 0.9762 0.8816 0.7457 0.123 Uiso 1 1 calc R . .
C4 C 0.2780(9) -0.2112(7) 0.1521(6) 0.099(3) Uani 1 1 d . . .
C15 C 0.6884(9) 0.3108(10) 0.1967(7) 0.106(3) Uani 1 1 d . . .
C16 C 0.6737(9) 0.4093(9) 0.1568(7) 0.104(3) Uani 1 1 d . . .
C14 C 0.6906(9) 0.2056(9) 0.1636(6) 0.110(3) Uani 1 1 d . . .
H14 H 0.6709 0.1890 0.1074 0.131 Uiso 1 1 calc R . .
C41 C 0.3375(10) 0.4105(8) 0.3867(6) 0.107(3) Uani 1 1 d . . .
H41 H 0.3375 0.3330 0.3797 0.128 Uiso 1 1 calc R . .
C34 C 0.8941(8) 0.6796(8) 0.3870(7) 0.111(3) Uani 1 1 d . . .
H34A H 0.8648 0.6451 0.3308 0.133 Uiso 1 1 calc R . .
H34B H 0.9719 0.7385 0.3900 0.133 Uiso 1 1 calc R . .
C3 C 0.3124(11) -0.1505(8) 0.0917(6) 0.110(3) Uani 1 1 d . . .
H3A H 0.2503 -0.1504 0.0469 0.133 Uiso 1 1 calc R . .
C7 C 0.1388(11) -0.2830(9) 0.1475(8) 0.128(4) Uani 1 1 d . . .
C6 C 0.5006(11) -0.1450(9) 0.2250(7) 0.121(3) Uani 1 1 d . . .
H6 H 0.5619 -0.1420 0.2710 0.145 Uiso 1 1 calc R . .
C2 C 0.4362(11) -0.0890(7) 0.0945(5) 0.103(3) Uani 1 1 d . . .
H2 H 0.4556 -0.0480 0.0523 0.124 Uiso 1 1 calc R . .
C5 C 0.3740(11) -0.2072(9) 0.2195(7) 0.126(4) Uani 1 1 d . . .
H5 H 0.3532 -0.2471 0.2619 0.151 Uiso 1 1 calc R . .
C32 C 0.8158(9) 0.8486(9) 0.4272(8) 0.152(5) Uani 1 1 d . . .
H32A H 0.8381 0.8811 0.3796 0.182 Uiso 1 1 calc R . .
H32B H 0.8893 0.8766 0.4709 0.182 Uiso 1 1 calc RD . .
C33 C 0.7973(8) 0.7343(8) 0.4118(10) 0.186(7) Uani 1 1 d . . .
H33 H 0.8175 0.7232 0.4689 0.223 Uiso 1 1 calc RD . .
C12 C 0.7208(16) 0.2483(11) 0.3263(7) 0.157(5) Uani 1 1 d . . .
H12 H 0.6325 0.2195 0.3322 0.188 Uiso 1 1 calc R . .
C21 C 0.6855(13) 0.4177(11) 0.0763(9) 0.159(5) Uani 1 1 d . . .
H21 H 0.7030 0.3567 0.0463 0.191 Uiso 1 1 calc R . .
C19 C 0.6513(16) 0.6037(13) 0.0758(12) 0.183(6) Uani 1 1 d . . .
H19 H 0.6451 0.6678 0.0501 0.219 Uiso 1 1 calc R . .
C17 C 0.6473(13) 0.5040(12) 0.1962(8) 0.165(5) Uani 1 1 d . . .
H17 H 0.6353 0.5046 0.2494 0.198 Uiso 1 1 calc R . .
C20 C 0.6720(14) 0.5146(13) 0.0392(9) 0.167(5) Uani 1 1 d . . .
H20 H 0.6785 0.5141 -0.0150 0.200 Uiso 1 1 calc R . .
C11 C 0.7394(19) 0.1460(17) 0.2959(8) 0.249(10) Uani 1 1 d . . .
H11A H 0.6826 0.0852 0.3154 0.298 Uiso 1 1 calc R . .
H11B H 0.8257 0.1439 0.3189 0.298 Uiso 1 1 calc R . .
C18 C 0.6387(19) 0.6002(12) 0.1550(12) 0.207(7) Uani 1 1 d . . .
H18 H 0.6238 0.6641 0.1831 0.248 Uiso 1 1 calc R . .
C9 C 0.0616(13) -0.2979(17) 0.0633(10) 0.282(11) Uani 1 1 d . . .
H9A H -0.0031 -0.3686 0.0541 0.423 Uiso 1 1 calc R . .
H9B H 0.1162 -0.2997 0.0247 0.423 Uiso 1 1 calc R . .
H9C H 0.0225 -0.2348 0.0572 0.423 Uiso 1 1 calc R . .
C8 C 0.0903(15) -0.2345(17) 0.2139(13) 0.307(14) Uani 1 1 d . . .
H8A H 0.0372 -0.1858 0.1941 0.460 Uiso 1 1 calc R . .
H8B H 0.1604 -0.1902 0.2547 0.460 Uiso 1 1 calc R . .
H8C H 0.0414 -0.2955 0.2368 0.460 Uiso 1 1 calc R . .
C10 C 0.1372(17) -0.4073(11) 0.1578(13) 0.283(11) Uani 1 1 d . . .
H10A H 0.2179 -0.4110 0.1883 0.424 Uiso 1 1 calc R . .
H10B H 0.1217 -0.4519 0.1055 0.424 Uiso 1 1 calc R . .
H10C H 0.0709 -0.4376 0.1861 0.424 Uiso 1 1 calc R . .
C31 C 0.8909(17) 0.7240(12) 0.8412(8) 0.212(7) Uani 1 1 d . . .
H31A H 0.9792 0.7630 0.8479 0.318 Uiso 1 1 calc R . .
H31B H 0.8646 0.6748 0.7904 0.318 Uiso 1 1 calc R . .
H31C H 0.8793 0.6788 0.8846 0.318 Uiso 1 1 calc R . .
C29 C 0.8832(19) 0.9103(13) 0.9142(7) 0.248(10) Uani 1 1 d . . .
H29A H 0.8311 0.9633 0.9207 0.372 Uiso 1 1 calc R . .
H29B H 0.9625 0.9502 0.9021 0.372 Uiso 1 1 calc R . .
H29C H 0.8993 0.8775 0.9635 0.372 Uiso 1 1 calc R . .
C28 C 0.8117(12) 0.8116(10) 0.8425(7) 0.131(4) Uani 1 1 d . . .
C30 C 0.6886(17) 0.752(2) 0.8625(12) 0.372(18) Uani 1 1 d . . .
H30A H 0.6482 0.6865 0.8226 0.558 Uiso 1 1 calc R . .
H30B H 0.6341 0.8040 0.8629 0.558 Uiso 1 1 calc R . .
H30C H 0.7042 0.7274 0.9150 0.558 Uiso 1 1 calc R . .
C13 C 0.772(2) 0.2959(12) 0.4088(9) 0.260(11) Uani 1 1 d . . .
H13A H 0.7146 0.3385 0.4270 0.312 Uiso 1 1 calc R . .
H13B H 0.7716 0.2327 0.4406 0.312 Uiso 1 1 calc R . .
O3 O 0.8959(8) 0.3691(8) 0.4274(4) 0.148(3) Uani 1 1 d . . .
H3 H 0.9284 0.3680 0.3872 0.221 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 O5 1.438(5) . ?
S2 O6 1.455(5) . ?
S2 N2 1.667(7) . ?
S2 C22 1.726(9) . ?
S1 O1 1.429(7) . ?
S1 O2 1.449(6) . ?
S1 N1 1.667(8) . ?
S1 C1 1.787(9) . ?
O8 C36 1.396(8) . ?
O8 C33 1.414(9) . ?
N2 C35 1.432(8) . ?
N2 C32 1.431(11) . ?
C36 C35 1.336(9) . ?
C36 C37 1.496(9) . ?
C37 C38 1.384(10) . ?
C37 C42 1.390(10) . ?
C35 H35 0.9300 . ?
O4 C12 1.383(13) . ?
O4 C15 1.395(11) . ?
O7 C34 1.375(10) . ?
O7 H7 0.8200 . ?
N1 C14 1.412(11) . ?
N1 C11 1.454(14) . ?
C22 C23 1.387(10) . ?
C22 C27 1.424(10) . ?
C23 C24 1.400(11) . ?
C23 H23 0.9300 . ?
C42 C41 1.425(11) . ?
C42 H42 0.9300 . ?
C24 C25 1.412(11) . ?
C24 H24 0.9300 . ?
C40 C41 1.308(12) . ?
C40 C39 1.375(12) . ?
C40 H40 0.9300 . ?
C1 C6 1.383(12) . ?
C1 C2 1.403(11) . ?
C27 C26 1.397(12) . ?
C27 H27 0.9300 . ?
C39 C38 1.411(10) . ?
C39 H39 0.9300 . ?
C38 H38 0.9300 . ?
C25 C26 1.418(12) . ?
C25 C28 1.517(13) . ?
C26 H26 0.9300 . ?
C4 C3 1.364(12) . ?
C4 C5 1.404(12) . ?
C4 C7 1.563(13) . ?
C15 C14 1.347(13) . ?
C15 C16 1.444(13) . ?
C16 C17 1.382(15) . ?
C16 C21 1.399(14) . ?
C14 H14 0.9300 . ?
C41 H41 0.9300 . ?
C34 C33 1.470(12) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C3 C2 1.385(12) . ?
C3 H3A 0.9300 . ?
C7 C8 1.453(18) . ?
C7 C9 1.501(16) . ?
C7 C10 1.521(16) . ?
C6 C5 1.407(13) . ?
C6 H6 0.9300 . ?
C2 H2 0.9300 . ?
C5 H5 0.9300 . ?
C32 C33 1.340(9) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 H33 0.9800 . ?
C12 C11 1.364(16) . ?
C12 C13 1.426(16) . ?
C12 H12 0.9800 . ?
C21 C20 1.398(14) . ?
C21 H21 0.9300 . ?
C19 C20 1.276(17) . ?
C19 C18 1.372(18) . ?
C19 H19 0.9300 . ?
C17 C18 1.417(18) . ?
C17 H17 0.9300 . ?
C20 H20 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C18 H18 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C31 C28 1.514(15) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C29 C28 1.580(15) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C28 C30 1.490(17) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C13 O3 1.411(18) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
O3 H3 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
O5 S2 O6 119.4(3) . . ?
O5 S2 N2 107.1(3) . . ?
O6 S2 N2 105.6(3) . . ?
O5 S2 C22 108.5(4) . . ?
O6 S2 C22 108.2(3) . . ?
N2 S2 C22 107.6(3) . . ?
O1 S1 O2 121.7(5) . . ?
O1 S1 N1 104.8(4) . . ?
O2 S1 N1 105.7(4) . . ?
O1 S1 C1 107.8(4) . . ?
O2 S1 C1 107.3(4) . . ?
N1 S1 C1 109.0(4) . . ?
C36 O8 C33 114.8(6) . . ?
C35 N2 C32 115.8(6) . . ?
C35 N2 S2 118.3(5) . . ?
C32 N2 S2 118.4(6) . . ?
C35 C36 O8 122.1(6) . . ?
C35 C36 C37 125.6(7) . . ?
O8 C36 C37 112.3(6) . . ?
C38 C37 C42 117.8(7) . . ?
C38 C37 C36 121.9(7) . . ?
C42 C37 C36 120.3(6) . . ?
C36 C35 N2 122.5(6) . . ?
C36 C35 H35 118.8 . . ?
N2 C35 H35 118.8 . . ?
C12 O4 C15 117.4(10) . . ?
C34 O7 H7 109.5 . . ?
C14 N1 C11 115.2(10) . . ?
C14 N1 S1 121.0(7) . . ?
C11 N1 S1 121.4(10) . . ?
C23 C22 C27 117.5(8) . . ?
C23 C22 S2 120.6(6) . . ?
C27 C22 S2 121.8(7) . . ?
C22 C23 C24 121.3(8) . . ?
C22 C23 H23 119.4 . . ?
C24 C23 H23 119.4 . . ?
C37 C42 C41 119.4(8) . . ?
C37 C42 H42 120.3 . . ?
C41 C42 H42 120.3 . . ?
C23 C24 C25 123.6(9) . . ?
C23 C24 H24 118.2 . . ?
C25 C24 H24 118.2 . . ?
C41 C40 C39 120.3(9) . . ?
C41 C40 H40 119.8 . . ?
C39 C40 H40 119.8 . . ?
C6 C1 C2 119.2(9) . . ?
C6 C1 S1 119.4(8) . . ?
C2 C1 S1 121.3(7) . . ?
C26 C27 C22 119.7(8) . . ?
C26 C27 H27 120.1 . . ?
C22 C27 H27 120.1 . . ?
C40 C39 C38 119.7(8) . . ?
C40 C39 H39 120.1 . . ?
C38 C39 H39 120.2 . . ?
C37 C38 C39 120.9(8) . . ?
C37 C38 H38 119.6 . . ?
C39 C38 H38 119.6 . . ?
C24 C25 C26 113.5(8) . . ?
C24 C25 C28 125.1(10) . . ?
C26 C25 C28 121.4(9) . . ?
C27 C26 C25 124.2(8) . . ?
C27 C26 H26 117.9 . . ?
C25 C26 H26 117.9 . . ?
C3 C4 C5 116.9(9) . . ?
C3 C4 C7 122.3(10) . . ?
C5 C4 C7 120.8(9) . . ?
C14 C15 O4 119.7(9) . . ?
C14 C15 C16 128.6(11) . . ?
O4 C15 C16 111.6(11) . . ?
C17 C16 C21 114.6(11) . . ?
C17 C16 C15 121.9(12) . . ?
C21 C16 C15 123.5(11) . . ?
C15 C14 N1 124.4(10) . . ?
C15 C14 H14 117.8 . . ?
N1 C14 H14 117.8 . . ?
C40 C41 C42 121.9(9) . . ?
C40 C41 H41 119.1 . . ?
C42 C41 H41 119.1 . . ?
O7 C34 C33 114.1(10) . . ?
O7 C34 H34A 108.7 . . ?
C33 C34 H34A 108.7 . . ?
O7 C34 H34B 108.7 . . ?
C33 C34 H34B 108.7 . . ?
H34A C34 H34B 107.6 . . ?
C4 C3 C2 122.6(9) . . ?
C4 C3 H3A 118.7 . . ?
C2 C3 H3A 118.7 . . ?
C8 C7 C9 118.3(14) . . ?
C8 C7 C10 108.2(14) . . ?
C9 C7 C10 100.6(12) . . ?
C8 C7 C4 107.9(10) . . ?
C9 C7 C4 111.1(10) . . ?
C10 C7 C4 110.5(10) . . ?
C1 C6 C5 118.8(9) . . ?
C1 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
C3 C2 C1 120.1(8) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C4 C5 C6 122.3(9) . . ?
C4 C5 H5 118.8 . . ?
C6 C5 H5 118.9 . . ?
C33 C32 N2 118.8(8) . . ?
C33 C32 H32A 107.6 . . ?
N2 C32 H32A 107.6 . . ?
C33 C32 H32B 107.6 . . ?
N2 C32 H32B 107.6 . . ?
H32A C32 H32B 107.1 . . ?
C32 C33 O8 124.2(8) . . ?
C32 C33 C34 122.8(8) . . ?
O8 C33 C34 110.8(8) . . ?
C32 C33 H33 94.8 . . ?
O8 C33 H33 94.8 . . ?
C34 C33 H33 94.8 . . ?
C11 C12 O4 124.4(11) . . ?
C11 C12 C13 120.8(15) . . ?
O4 C12 C13 110.0(12) . . ?
C11 C12 H12 97.3 . . ?
O4 C12 H12 97.3 . . ?
C13 C12 H12 97.4 . . ?
C20 C21 C16 122.4(13) . . ?
C20 C21 H21 118.8 . . ?
C16 C21 H21 118.8 . . ?
C20 C19 C18 116.7(15) . . ?
C20 C19 H19 121.7 . . ?
C18 C19 H19 121.7 . . ?
C16 C17 C18 119.5(14) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C19 C20 C21 123.5(15) . . ?
C19 C20 H20 118.3 . . ?
C21 C20 H20 118.3 . . ?
C12 C11 N1 118.1(11) . . ?
C12 C11 H11A 107.8 . . ?
N1 C11 H11A 107.8 . . ?
C12 C11 H11B 107.8 . . ?
N1 C11 H11B 107.8 . . ?
H11A C11 H11B 107.1 . . ?
C19 C18 C17 123.3(16) . . ?
C19 C18 H18 118.3 . . ?
C17 C18 H18 118.3 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.4 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C8 H8A 109.4 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C28 C31 H31A 109.5 . . ?
C28 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C28 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.4 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C30 C28 C31 106.4(13) . . ?
C30 C28 C25 113.3(10) . . ?
C31 C28 C25 112.6(10) . . ?
C30 C28 C29 108.3(15) . . ?
C31 C28 C29 107.1(11) . . ?
C25 C28 C29 109.0(9) . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
O3 C13 C12 118.0(16) . . ?
O3 C13 H13A 107.8 . . ?
C12 C13 H13A 107.8 . . ?
O3 C13 H13B 107.8 . . ?
C12 C13 H13B 107.8 . . ?
H13A C13 H13B 107.2 . . ?
C13 O3 H3 109.4 . . ?

_diffrn_measured_fraction_theta_max 0.782
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_measured_fraction_theta_full 'ACTA 50'
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.059
_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_compound31
_database_code_depnum_ccdc_archive 'CCDC 1885285'
loop_
_audit_author_name
_audit_author_address
'K C Kumara Swamy'
;University of Hyderabad
India
;
_audit_update_record             
;
2018-12-15 deposited with the CCDC.	2019-02-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H16 Br3 N O2 S'
_chemical_formula_weight         538.10

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   8.2985(3)
_cell_length_b                   12.4303(6)
_cell_length_c                   19.4432(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.3220(10)
_cell_angle_gamma                90.00
_cell_volume                     1966.59(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    9919
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      25.83

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.817
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1048
_exptl_absorpt_coefficient_mu    6.269
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      300(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            32477
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_sigmaI/netI    0.0177
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.96
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3431
_reflns_number_gt                2936
_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)+(0.0459P)²+3.5045P] 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         3431
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.1036
_refine_ls_wR_factor_gt          0.0993
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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
Br3 Br 0.11460(6) 0.10429(4) 0.65042(2) 0.06600(17) Uani 1 1 d . . .
Br2 Br 0.34718(6) 0.33834(4) 0.51549(3) 0.07005(18) Uani 1 1 d . . .
Br1 Br 0.68552(9) -0.06278(6) 0.59063(4) 0.1029(3) Uani 1 1 d . . .
S1 S 0.48720(13) 0.28096(10) 0.71198(5) 0.0542(3) Uani 1 1 d . . .
N1 N 0.4419(4) 0.2119(3) 0.63739(17) 0.0496(8) Uani 1 1 d . . .
O2 O 0.3416(4) 0.3361(3) 0.71835(18) 0.0751(10) Uani 1 1 d . . .
O1 O 0.5634(5) 0.2050(3) 0.76335(18) 0.0848(12) Uani 1 1 d . . .
C1 C 0.6364(5) 0.3755(3) 0.70104(19) 0.0445(9) Uani 1 1 d . . .
C10 C 0.0066(5) 0.2350(3) 0.5299(2) 0.0472(9) Uani 1 1 d . . .
C8 C 0.3049(5) 0.2402(3) 0.5869(2) 0.0501(9) Uani 1 1 d . . .
C9 C 0.1551(5) 0.2039(3) 0.5824(2) 0.0496(9) Uani 1 1 d . . .
C15 C -0.0574(6) 0.1652(4) 0.4765(2) 0.0591(11) Uani 1 1 d . . .
H15 H -0.0060 0.0996 0.4726 0.071 Uiso 1 1 calc R . .
C6 C 0.8012(5) 0.3491(4) 0.7209(3) 0.0606(11) Uani 1 1 d . . .
H6 H 0.8330 0.2827 0.7411 0.073 Uiso 1 1 calc R . .
C2 C 0.5913(6) 0.4752(4) 0.6734(2) 0.0569(11) Uani 1 1 d . . .
H2 H 0.4806 0.4933 0.6612 0.068 Uiso 1 1 calc R . .
C3 C 0.7080(7) 0.5477(4) 0.6639(2) 0.0697(13) Uani 1 1 d . . .
H3 H 0.6760 0.6152 0.6455 0.084 Uiso 1 1 calc R . .
C4 C 0.8713(7) 0.5228(5) 0.6808(2) 0.0714(15) Uani 1 1 d . . .
C5 C 0.9177(6) 0.4237(5) 0.7100(3) 0.0738(15) Uani 1 1 d . . .
H5 H 1.0287 0.4067 0.7226 0.089 Uiso 1 1 calc R . .
C14 C -0.1980(6) 0.1924(5) 0.4287(3) 0.0706(14) Uani 1 1 d . . .
H14 H -0.2392 0.1459 0.3920 0.085 Uiso 1 1 calc R . .
C16 C 0.5703(6) 0.1433(4) 0.6149(3) 0.0638(12) Uani 1 1 d . . .
H16A H 0.5749 0.1584 0.5664 0.077 Uiso 1 1 calc R . .
H16B H 0.6771 0.1590 0.6436 0.077 Uiso 1 1 calc R . .
C11 C -0.0698(7) 0.3313(5) 0.5345(3) 0.0763(15) Uani 1 1 d . . .
H11 H -0.0263 0.3808 0.5691 0.092 Uiso 1 1 calc R . .
C13 C -0.2751(6) 0.2856(6) 0.4351(3) 0.0762(15) Uani 1 1 d . . .
H13 H -0.3714 0.3024 0.4036 0.091 Uiso 1 1 calc R . .
C12 C -0.2140(8) 0.3544(6) 0.4865(3) 0.0908(19) Uani 1 1 d . . .
H12 H -0.2686 0.4188 0.4904 0.109 Uiso 1 1 calc R . .
C17 C 0.5286(8) 0.0283(5) 0.6227(4) 0.0887(17) Uani 1 1 d . . .
H17A H 0.4195 0.0137 0.5958 0.106 Uiso 1 1 calc R . .
H17B H 0.5283 0.0129 0.6716 0.106 Uiso 1 1 calc R . .
C7 C 1.0014(11) 0.6023(7) 0.6682(4) 0.134(4) Uani 1 1 d . . .
H7A H 1.0103 0.6000 0.6197 0.201 Uiso 1 1 calc R . .
H7B H 1.1053 0.5835 0.6970 0.201 Uiso 1 1 calc R . .
H7C H 0.9710 0.6735 0.6798 0.201 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
Br3 C9 1.890(4) . ?
Br2 C8 1.931(4) . ?
Br1 C17 1.919(6) . ?
S1 O2 1.416(4) . ?
S1 O1 1.429(4) . ?
S1 N1 1.663(3) . ?
S1 C1 1.750(4) . ?
N1 C8 1.394(5) . ?
N1 C16 1.496(6) . ?
C1 C2 1.374(6) . ?
C1 C6 1.385(6) . ?
C10 C11 1.366(6) . ?
C10 C15 1.377(6) . ?
C10 C9 1.488(5) . ?
C8 C9 1.309(6) . ?
C15 C14 1.384(6) . ?
C15 H15 0.9300 . ?
C6 C5 1.385(7) . ?
C6 H6 0.9300 . ?
C2 C3 1.362(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.365(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.379(8) . ?
C4 C7 1.519(7) . ?
C5 H5 0.9300 . ?
C14 C13 1.340(8) . ?
C14 H14 0.9300 . ?
C16 C17 1.486(7) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C11 C12 1.395(8) . ?
C11 H11 0.9300 . ?
C13 C12 1.338(9) . ?
C13 H13 0.9300 . ?
C12 H12 0.9300 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 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 121.8(3) . . ?
O2 S1 N1 105.99(18) . . ?
O1 S1 N1 105.2(2) . . ?
O2 S1 C1 108.8(2) . . ?
O1 S1 C1 107.6(2) . . ?
N1 S1 C1 106.53(18) . . ?
C8 N1 C16 117.8(3) . . ?
C8 N1 S1 119.9(3) . . ?
C16 N1 S1 119.8(3) . . ?
C2 C1 C6 120.0(4) . . ?
C2 C1 S1 120.5(3) . . ?
C6 C1 S1 119.4(3) . . ?
C11 C10 C15 119.1(4) . . ?
C11 C10 C9 121.0(4) . . ?
C15 C10 C9 119.9(4) . . ?
C9 C8 N1 126.4(4) . . ?
C9 C8 Br2 118.3(3) . . ?
N1 C8 Br2 115.3(3) . . ?
C8 C9 C10 127.2(4) . . ?
C8 C9 Br3 118.4(3) . . ?
C10 C9 Br3 114.4(3) . . ?
C10 C15 C14 120.1(5) . . ?
C10 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C5 C6 C1 118.7(5) . . ?
C5 C6 H6 120.7 . . ?
C1 C6 H6 120.7 . . ?
C3 C2 C1 120.2(4) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 121.0(5) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C5 119.0(4) . . ?
C3 C4 C7 121.1(7) . . ?
C5 C4 C7 119.8(6) . . ?
C4 C5 C6 120.9(5) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C13 C14 C15 120.3(5) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C17 C16 N1 109.0(4) . . ?
C17 C16 H16A 109.9 . . ?
N1 C16 H16A 109.9 . . ?
C17 C16 H16B 109.9 . . ?
N1 C16 H16B 109.9 . . ?
H16A C16 H16B 108.3 . . ?
C10 C11 C12 119.0(5) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
C12 C13 C14 120.2(5) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C12 C11 121.2(5) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C16 C17 Br1 110.4(4) . . ?
C16 C17 H17A 109.6 . . ?
Br1 C17 H17A 109.6 . . ?
C16 C17 H17B 109.6 . . ?
Br1 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.669
_refine_diff_density_min         -0.826
_refine_diff_density_rms         0.072
_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_compound8
_database_code_depnum_ccdc_archive 'CCDC 1885281'
loop_
_audit_author_name
_audit_author_address
'K C Kumara Swamy'
;University of Hyderabad
India
;
_audit_update_record             
;
2018-12-15 deposited with the CCDC.	2019-02-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H14 Br3 N O3 S'
_chemical_formula_weight         552.08

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.9458(2)
_cell_length_b                   10.9848(2)
_cell_length_c                   12.6203(4)
_cell_angle_alpha                95.166(2)
_cell_angle_beta                 94.677(2)
_cell_angle_gamma                97.680(2)
_cell_volume                     946.11(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6234
_cell_measurement_theta_min      2.3490
_cell_measurement_theta_max      26.3150

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.938
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    6.522
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12838
_diffrn_reflns_av_R_equivalents  0.0630
_diffrn_reflns_av_sigmaI/netI    0.0641
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         27.27
_reflns_number_total             3962
_reflns_number_gt                2801
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.40.22a (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.22a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.22a (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXS-97 (Sheldrick, 2008)'
_computing_publication_material  'SHELXS-97 (Sheldrick, 2008)'

_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)+(0.0564P)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         3962
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0809
_refine_ls_R_factor_gt           0.0509
_refine_ls_wR_factor_ref         0.1223
_refine_ls_wR_factor_gt          0.1129
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_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
Br3 Br 0.89389(6) 0.52423(5) 0.82216(4) 0.04976(18) Uani 1 1 d . . .
Br1 Br -0.19082(9) 0.20552(6) 0.33380(5) 0.0711(2) Uani 1 1 d . . .
Br2 Br 0.01521(9) 0.06736(6) 0.86335(6) 0.0758(2) Uani 1 1 d . . .
S1 S 0.62726(16) 0.26873(11) 0.61722(10) 0.0390(3) Uani 1 1 d . . .
O3 O 0.3100(4) 0.3883(3) 0.7806(3) 0.0409(8) Uani 1 1 d . . .
O2 O 0.7430(4) 0.3788(3) 0.5970(3) 0.0499(9) Uani 1 1 d . . .
O1 O 0.7013(5) 0.1536(3) 0.6097(3) 0.0534(9) Uani 1 1 d . . .
N1 N 0.5723(5) 0.2896(3) 0.7451(3) 0.0337(8) Uani 1 1 d . . .
C11 C 0.6191(6) 0.5108(4) 0.8156(3) 0.0311(10) Uani 1 1 d . . .
C12 C 0.5422(6) 0.6242(4) 0.8553(3) 0.0307(10) Uani 1 1 d . . .
C10 C 0.5110(6) 0.4043(4) 0.7801(3) 0.0302(10) Uani 1 1 d . . .
C13 C 0.3935(6) 0.6190(4) 0.9214(3) 0.0382(11) Uani 1 1 d . . .
H13 H 0.3398 0.5429 0.9408 0.046 Uiso 1 1 calc R . .
C1 C 0.4036(6) 0.2511(4) 0.5370(3) 0.0364(10) Uani 1 1 d . . .
C7 C 0.4211(6) 0.1943(4) 0.7746(4) 0.0397(11) Uani 1 1 d . . .
H7A H 0.4567 0.1694 0.8446 0.048 Uiso 1 1 calc R . .
H7B H 0.4011 0.1221 0.7226 0.048 Uiso 1 1 calc R . .
C8 C 0.2380(6) 0.2581(4) 0.7753(4) 0.0416(11) Uani 1 1 d . . .
H8 H 0.1553 0.2325 0.7082 0.050 Uiso 1 1 calc R . .
C4 C 0.0523(7) 0.2238(5) 0.4170(3) 0.0425(12) Uani 1 1 d . . .
C2 C 0.3150(7) 0.1337(4) 0.4946(4) 0.0441(12) Uani 1 1 d . . .
H2 H 0.3749 0.0649 0.5070 0.053 Uiso 1 1 calc R . .
C17 C 0.6220(7) 0.7396(4) 0.8294(4) 0.0453(12) Uani 1 1 d . . .
H17 H 0.7241 0.7453 0.7860 0.054 Uiso 1 1 calc R . .
C14 C 0.3224(7) 0.7254(5) 0.9597(4) 0.0479(13) Uani 1 1 d . . .
H14 H 0.2209 0.7205 1.0036 0.057 Uiso 1 1 calc R . .
C6 C 0.3163(7) 0.3537(4) 0.5182(4) 0.0427(12) Uani 1 1 d . . .
H6 H 0.3774 0.4317 0.5463 0.051 Uiso 1 1 calc R . .
C3 C 0.1381(7) 0.1206(5) 0.4345(4) 0.0493(13) Uani 1 1 d . . .
H3 H 0.0769 0.0427 0.4058 0.059 Uiso 1 1 calc R . .
C5 C 0.1401(7) 0.3409(4) 0.4585(4) 0.0458(12) Uani 1 1 d . . .
H5 H 0.0802 0.4097 0.4459 0.055 Uiso 1 1 calc R . .
C15 C 0.4032(7) 0.8376(5) 0.9320(4) 0.0504(13) Uani 1 1 d . . .
H15 H 0.3567 0.9090 0.9576 0.060 Uiso 1 1 calc R . .
C16 C 0.5525(7) 0.8452(4) 0.8668(4) 0.0525(14) Uani 1 1 d . . .
H16 H 0.6063 0.9215 0.8480 0.063 Uiso 1 1 calc R . .
C9 C 0.1206(8) 0.2390(5) 0.8661(5) 0.0641(16) Uani 1 1 d . . .
H9A H 0.0149 0.2883 0.8625 0.077 Uiso 1 1 calc R . .
H9B H 0.2016 0.2655 0.9326 0.077 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
Br3 C11 1.889(4) . ?
Br1 C4 1.891(4) . ?
Br2 C9 1.925(6) . ?
S1 O2 1.415(3) . ?
S1 O1 1.426(3) . ?
S1 N1 1.691(4) . ?
S1 C1 1.762(4) . ?
O3 C10 1.384(4) . ?
O3 C8 1.444(5) . ?
N1 C10 1.427(5) . ?
N1 C7 1.476(5) . ?
C11 C10 1.323(5) . ?
C11 C12 1.482(5) . ?
C12 C13 1.379(6) . ?
C12 C17 1.391(6) . ?
C13 C14 1.392(6) . ?
C13 H13 0.9300 . ?
C1 C6 1.378(6) . ?
C1 C2 1.392(6) . ?
C7 C8 1.533(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.474(7) . ?
C8 H8 0.9800 . ?
C4 C3 1.375(6) . ?
C4 C5 1.385(6) . ?
C2 C3 1.374(6) . ?
C2 H2 0.9300 . ?
C17 C16 1.375(6) . ?
C17 H17 0.9300 . ?
C14 C15 1.371(7) . ?
C14 H14 0.9300 . ?
C6 C5 1.368(6) . ?
C6 H6 0.9300 . ?
C3 H3 0.9300 . ?
C5 H5 0.9300 . ?
C15 C16 1.374(7) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?

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 121.0(2) . . ?
O2 S1 N1 106.73(19) . . ?
O1 S1 N1 104.53(19) . . ?
O2 S1 C1 109.1(2) . . ?
O1 S1 C1 108.4(2) . . ?
N1 S1 C1 106.07(19) . . ?
C10 O3 C8 109.4(3) . . ?
C10 N1 C7 104.8(3) . . ?
C10 N1 S1 117.6(3) . . ?
C7 N1 S1 114.5(3) . . ?
C10 C11 C12 125.0(4) . . ?
C10 C11 Br3 119.8(3) . . ?
C12 C11 Br3 115.2(3) . . ?
C13 C12 C17 118.0(4) . . ?
C13 C12 C11 121.0(4) . . ?
C17 C12 C11 121.0(4) . . ?
C11 C10 O3 121.6(4) . . ?
C11 C10 N1 128.8(4) . . ?
O3 C10 N1 109.4(3) . . ?
C12 C13 C14 121.2(5) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C6 C1 C2 120.6(4) . . ?
C6 C1 S1 119.6(3) . . ?
C2 C1 S1 119.8(3) . . ?
N1 C7 C8 103.8(3) . . ?
N1 C7 H7A 111.0 . . ?
C8 C7 H7A 111.0 . . ?
N1 C7 H7B 111.0 . . ?
C8 C7 H7B 111.0 . . ?
H7A C7 H7B 109.0 . . ?
O3 C8 C9 107.8(4) . . ?
O3 C8 C7 104.8(3) . . ?
C9 C8 C7 115.9(4) . . ?
O3 C8 H8 109.4 . . ?
C9 C8 H8 109.4 . . ?
C7 C8 H8 109.4 . . ?
C3 C4 C5 121.6(4) . . ?
C3 C4 Br1 119.3(4) . . ?
C5 C4 Br1 119.1(4) . . ?
C3 C2 C1 119.4(4) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C16 C17 C12 121.2(5) . . ?
C16 C17 H17 119.4 . . ?
C12 C17 H17 119.4 . . ?
C15 C14 C13 119.3(5) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C5 C6 C1 120.2(4) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
C2 C3 C4 119.4(4) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C6 C5 C4 118.9(4) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C14 C15 C16 120.6(4) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C17 119.7(5) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C8 C9 Br2 110.4(4) . . ?
C8 C9 H9A 109.6 . . ?
Br2 C9 H9A 109.6 . . ?
C8 C9 H9B 109.6 . . ?
Br2 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?

_diffrn_measured_fraction_theta_max 0.934
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_measured_fraction_theta_full 'ACTA 50'
_refine_diff_density_max         0.663
_refine_diff_density_min         -0.792
_refine_diff_density_rms         0.105
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
