# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

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

data_Compound3aa
_database_code_depnum_ccdc_archive 'CCDC 2082515'
loop_
_audit_author_name
_audit_author_address
'K C Kumara Swamy'
;University of Hyderabad
India
;
_audit_update_record             
;
2021-05-08 deposited with the CCDC.	2021-07-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H19 N O2 S'
_chemical_formula_weight         361.44

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                   11.613(2)
_cell_length_b                   10.494(2)
_cell_length_c                   15.562(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.952(6)
_cell_angle_gamma                90.00
_cell_volume                     1895.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    9516
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      27.21

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760
_exptl_absorpt_coefficient_mu    0.186
_exptl_absorpt_correction_type   none
_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_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            42063
_diffrn_reflns_av_R_equivalents  0.0732
_diffrn_reflns_av_sigmaI/netI    0.0270
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_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         2.23
_diffrn_reflns_theta_max         24.98
_reflns_number_total             3331
_reflns_number_gt                2576
_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, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0484P)²+0.9318P] 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       0.0105(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3331
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0436
_refine_ls_wR_factor_ref         0.1138
_refine_ls_wR_factor_gt          0.1065
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.55500(4) 0.42291(6) 0.78033(4) 0.0386(2) Uani 1 1 d . . .
O1 O 0.63600(13) 0.32556(17) 0.76151(11) 0.0548(5) Uani 1 1 d . . .
O2 O 0.60279(14) 0.54709(17) 0.79469(12) 0.0559(5) Uani 1 1 d . . .
N1 N 0.45153(14) 0.4271(2) 0.70443(11) 0.0426(5) Uani 1 1 d . . .
C9 C 0.24234(17) 0.4097(2) 0.68501(13) 0.0331(5) Uani 1 1 d . . .
C10 C 0.12674(17) 0.4258(2) 0.72223(13) 0.0325(5) Uani 1 1 d . . .
C6 C 0.34788(17) 0.3838(2) 0.82987(13) 0.0342(5) Uani 1 1 d . . .
C8 C 0.33864(17) 0.4105(2) 0.73593(13) 0.0341(5) Uani 1 1 d . . .
C16 C 0.24094(17) 0.3945(2) 0.58981(13) 0.0358(5) Uani 1 1 d . . .
C1 C 0.46150(18) 0.3814(2) 0.86043(14) 0.0371(5) Uani 1 1 d . . .
C5 C 0.26290(19) 0.3524(2) 0.88719(14) 0.0425(6) Uani 1 1 d . . .
H5 H 0.1861 0.3512 0.8683 0.051 Uiso 1 1 calc R . .
C15 C 0.04352(17) 0.3311(2) 0.71515(14) 0.0380(5) Uani 1 1 d . . .
H15 H 0.0602 0.2548 0.6878 0.046 Uiso 1 1 calc R . .
C2 C 0.4926(2) 0.3507(2) 0.94477(15) 0.0491(6) Uani 1 1 d . . .
H2 H 0.5696 0.3491 0.9634 0.059 Uiso 1 1 calc R . .
C14 C -0.06410(19) 0.3497(3) 0.74857(15) 0.0464(6) Uani 1 1 d . . .
H14 H -0.1192 0.2856 0.7441 0.056 Uiso 1 1 calc R . .
C11 C 0.09917(19) 0.5393(2) 0.76211(15) 0.0436(6) Uani 1 1 d . . .
H11 H 0.1538 0.6039 0.7666 0.052 Uiso 1 1 calc R . .
C4 C 0.2915(2) 0.3231(2) 0.97196(14) 0.0470(6) Uani 1 1 d . . .
C3 C 0.4067(2) 0.3227(3) 0.99963(15) 0.0529(7) Uani 1 1 d . . .
H3 H 0.4257 0.3029 1.0566 0.064 Uiso 1 1 calc R . .
C13 C -0.0898(2) 0.4625(3) 0.78830(16) 0.0490(6) Uani 1 1 d . . .
H13 H -0.1623 0.4747 0.8106 0.059 Uiso 1 1 calc R . .
C17 C 0.1704(2) 0.4703(3) 0.53743(15) 0.0507(6) Uani 1 1 d . . .
H17 H 0.1242 0.5317 0.5621 0.061 Uiso 1 1 calc R . .
C21 C 0.3047(2) 0.3007(3) 0.55092(15) 0.0508(6) Uani 1 1 d . . .
H21 H 0.3507 0.2465 0.5846 0.061 Uiso 1 1 calc R . .
C12 C -0.0083(2) 0.5577(2) 0.79517(17) 0.0505(6) Uani 1 1 d . . .
H12 H -0.0256 0.6341 0.8220 0.061 Uiso 1 1 calc R . .
C19 C 0.2332(3) 0.3656(3) 0.41191(17) 0.0655(9) Uani 1 1 d . . .
H19 H 0.2321 0.3573 0.3524 0.079 Uiso 1 1 calc R . .
C18 C 0.1679(2) 0.4560(3) 0.44925(17) 0.0649(8) Uani 1 1 d . . .
H18 H 0.1210 0.5087 0.4151 0.078 Uiso 1 1 calc R . .
C22 C 0.4739(2) 0.5138(3) 0.63267(17) 0.0654(8) Uani 1 1 d . . .
H22A H 0.4616 0.4694 0.5792 0.098 Uiso 1 1 calc R . .
H22B H 0.5521 0.5432 0.6373 0.098 Uiso 1 1 calc R . .
H22C H 0.4226 0.5853 0.6347 0.098 Uiso 1 1 calc R . .
C20 C 0.3007(2) 0.2867(3) 0.46224(17) 0.0635(8) Uani 1 1 d . . .
H20 H 0.3441 0.2233 0.4369 0.076 Uiso 1 1 calc R . .
C7 C 0.1982(3) 0.2917(3) 1.03360(17) 0.0729(9) Uani 1 1 d . . .
H7A H 0.1309 0.3418 1.0197 0.109 Uiso 1 1 calc R . .
H7B H 0.2249 0.3103 1.0913 0.109 Uiso 1 1 calc R . .
H7C H 0.1793 0.2028 1.0290 0.109 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 1.4258(17) . ?
S1 O2 1.4309(18) . ?
S1 N1 1.6565(18) . ?
S1 C1 1.736(2) . ?
N1 C8 1.426(3) . ?
N1 C22 1.470(3) . ?
C9 C8 1.348(3) . ?
C9 C16 1.489(3) . ?
C9 C10 1.490(3) . ?
C10 C11 1.386(3) . ?
C10 C15 1.388(3) . ?
C6 C1 1.387(3) . ?
C6 C5 1.392(3) . ?
C6 C8 1.489(3) . ?
C16 C21 1.383(3) . ?
C16 C17 1.387(3) . ?
C1 C2 1.387(3) . ?
C5 C4 1.384(3) . ?
C5 H5 0.9300 . ?
C15 C14 1.384(3) . ?
C15 H15 0.9300 . ?
C2 C3 1.367(3) . ?
C2 H2 0.9300 . ?
C14 C13 1.373(4) . ?
C14 H14 0.9300 . ?
C11 C12 1.379(3) . ?
C11 H11 0.9300 . ?
C4 C3 1.391(3) . ?
C4 C7 1.508(3) . ?
C3 H3 0.9300 . ?
C13 C12 1.378(4) . ?
C13 H13 0.9300 . ?
C17 C18 1.380(4) . ?
C17 H17 0.9300 . ?
C21 C20 1.387(3) . ?
C21 H21 0.9300 . ?
C12 H12 0.9300 . ?
C19 C18 1.358(4) . ?
C19 C20 1.368(4) . ?
C19 H19 0.9300 . ?
C18 H18 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C20 H20 0.9300 . ?
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 115.44(11) . . ?
O1 S1 N1 109.88(11) . . ?
O2 S1 N1 110.81(11) . . ?
O1 S1 C1 113.62(11) . . ?
O2 S1 C1 111.41(11) . . ?
N1 S1 C1 93.58(9) . . ?
C8 N1 C22 121.68(19) . . ?
C8 N1 S1 113.87(14) . . ?
C22 N1 S1 114.54(15) . . ?
C8 C9 C16 124.47(18) . . ?
C8 C9 C10 120.73(18) . . ?
C16 C9 C10 114.80(17) . . ?
C11 C10 C15 118.7(2) . . ?
C11 C10 C9 119.78(19) . . ?
C15 C10 C9 121.5(2) . . ?
C1 C6 C5 117.57(19) . . ?
C1 C6 C8 112.07(18) . . ?
C5 C6 C8 130.14(19) . . ?
C9 C8 N1 123.54(19) . . ?
C9 C8 C6 127.34(19) . . ?
N1 C8 C6 108.92(17) . . ?
C21 C16 C17 117.7(2) . . ?
C21 C16 C9 121.6(2) . . ?
C17 C16 C9 120.6(2) . . ?
C6 C1 C2 122.8(2) . . ?
C6 C1 S1 111.11(16) . . ?
C2 C1 S1 126.05(17) . . ?
C4 C5 C6 120.7(2) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C14 C15 C10 120.3(2) . . ?
C14 C15 H15 119.8 . . ?
C10 C15 H15 119.8 . . ?
C3 C2 C1 118.0(2) . . ?
C3 C2 H2 121.0 . . ?
C1 C2 H2 121.0 . . ?
C13 C14 C15 120.2(2) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C12 C11 C10 120.9(2) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C5 C4 C3 119.5(2) . . ?
C5 C4 C7 120.0(2) . . ?
C3 C4 C7 120.4(2) . . ?
C2 C3 C4 121.4(2) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C14 C13 C12 120.0(2) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C18 C17 C16 120.9(3) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C16 C21 C20 120.7(2) . . ?
C16 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C13 C12 C11 119.9(2) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C18 C19 C20 119.7(2) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C19 C18 C17 120.6(3) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
N1 C22 H22A 109.5 . . ?
N1 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N1 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C19 C20 C21 120.3(3) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
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        24.98
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.048
_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_Compound3jb
_database_code_depnum_ccdc_archive 'CCDC 2082518'
loop_
_audit_author_name
_audit_author_address
'K C Kumara Swamy'
;University of Hyderabad
India
;
_audit_update_record             
;
2021-05-08 deposited with the CCDC.	2021-07-19 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 H19 N O2 S2'
_chemical_formula_weight         381.49

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                   9.8974(2)
_cell_length_b                   9.9589(3)
_cell_length_c                   11.7524(3)
_cell_angle_alpha                90.477(2)
_cell_angle_beta                 106.658(2)
_cell_angle_gamma                116.051(2)
_cell_volume                     984.84(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7197
_cell_measurement_theta_min      2.2890
_cell_measurement_theta_max      26.6920

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             400
_exptl_absorpt_coefficient_mu    0.285
_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       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13154
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_sigmaI/netI    0.0286
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.83
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3470
_reflns_number_gt                2779
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0632P)²+0.3450P] 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       0.017(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3470
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1339
_refine_ls_wR_factor_gt          0.1261
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.32341(7) 0.24920(7) 0.78440(5) 0.0526(2) Uani 1 1 d . . .
S2 S 1.00225(9) 0.20307(10) 0.94401(6) 0.0735(3) Uani 1 1 d . . .
O2 O 0.3084(2) 0.3681(2) 0.83914(17) 0.0746(6) Uani 1 1 d . . .
O1 O 0.2456(2) 0.1023(2) 0.81522(17) 0.0741(6) Uani 1 1 d . . .
N1 N 0.5114(2) 0.2977(2) 0.80597(16) 0.0494(5) Uani 1 1 d . . .
C10 C 0.7152(2) 0.2753(2) 0.58406(19) 0.0402(5) Uani 1 1 d . . .
C8 C 0.5438(3) 0.2811(3) 0.69651(18) 0.0419(5) Uani 1 1 d . . .
C9 C 0.6726(2) 0.2660(2) 0.69625(19) 0.0418(5) Uani 1 1 d . . .
C6 C 0.4052(3) 0.2605(2) 0.59353(18) 0.0399(5) Uani 1 1 d . . .
C15 C 0.6973(3) 0.1482(3) 0.5196(2) 0.0449(5) Uani 1 1 d . . .
H15 H 0.6705 0.0584 0.5516 0.054 Uiso 1 1 calc R . .
C17 C 0.7688(3) 0.2289(3) 0.79939(19) 0.0456(5) Uani 1 1 d . . .
C5 C 0.3804(3) 0.2454(3) 0.4701(2) 0.0484(6) Uani 1 1 d . . .
H5 H 0.4644 0.2610 0.4423 0.058 Uiso 1 1 calc R . .
C1 C 0.2751(3) 0.2367(3) 0.6296(2) 0.0446(5) Uani 1 1 d . . .
C14 C 0.7187(3) 0.1531(3) 0.4089(2) 0.0507(6) Uani 1 1 d . . .
H14 H 0.7034 0.0656 0.3664 0.061 Uiso 1 1 calc R . .
C11 C 0.7648(3) 0.4086(3) 0.5366(2) 0.0564(6) Uani 1 1 d . . .
H11 H 0.7826 0.4969 0.5796 0.068 Uiso 1 1 calc R . .
C13 C 0.7623(3) 0.2842(3) 0.3592(2) 0.0537(6) Uani 1 1 d . . .
C2 C 0.1255(3) 0.1970(3) 0.5500(2) 0.0544(6) Uani 1 1 d . . .
H2 H 0.0409 0.1805 0.5774 0.065 Uiso 1 1 calc R . .
C4 C 0.2316(3) 0.2073(3) 0.3884(2) 0.0562(7) Uani 1 1 d . . .
C3 C 0.1059(3) 0.1828(3) 0.4299(2) 0.0586(7) Uani 1 1 d . . .
H3 H 0.0063 0.1562 0.3747 0.070 Uiso 1 1 calc R . .
C20 C 0.9269(3) 0.2728(3) 0.8240(2) 0.0569(7) Uani 1 1 d . . .
H20 H 0.9872 0.3345 0.7797 0.068 Uiso 1 1 calc R . .
C12 C 0.7882(4) 0.4122(3) 0.4260(2) 0.0637(7) Uani 1 1 d . . .
H12 H 0.8222 0.5033 0.3961 0.076 Uiso 1 1 calc R . .
C18 C 0.7095(3) 0.1335(3) 0.8816(2) 0.0598(7) Uani 1 1 d . . .
H18 H 0.6041 0.0905 0.8792 0.072 Uiso 1 1 calc R . .
C19 C 0.8258(3) 0.1121(3) 0.9649(2) 0.0642(7) Uani 1 1 d . . .
H19 H 0.8080 0.0539 1.0256 0.077 Uiso 1 1 calc R . .
C21 C 0.6325(3) 0.4125(4) 0.9087(2) 0.0726(8) Uani 1 1 d . . .
H21A H 0.7289 0.4662 0.8897 0.109 Uiso 1 1 calc R . .
H21B H 0.6524 0.3643 0.9775 0.109 Uiso 1 1 calc R . .
H21C H 0.5955 0.4822 0.9262 0.109 Uiso 1 1 calc R . .
C16 C 0.7819(5) 0.2880(4) 0.2362(3) 0.0862(10) Uani 1 1 d . . .
H16A H 0.7255 0.3370 0.1891 0.129 Uiso 1 1 calc R . .
H16B H 0.7399 0.1865 0.1969 0.129 Uiso 1 1 calc R . .
H16C H 0.8926 0.3430 0.2445 0.129 Uiso 1 1 calc R . .
C7 C 0.2085(4) 0.1932(5) 0.2556(2) 0.0928(11) Uani 1 1 d . . .
H7A H 0.3046 0.2049 0.2431 0.139 Uiso 1 1 calc R . .
H7B H 0.1830 0.2703 0.2229 0.139 Uiso 1 1 calc R . .
H7C H 0.1234 0.0954 0.2161 0.139 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 1.4266(19) . ?
S1 O1 1.430(2) . ?
S1 N1 1.6428(19) . ?
S1 C1 1.732(2) . ?
S2 C19 1.671(3) . ?
S2 C20 1.702(3) . ?
N1 C8 1.437(3) . ?
N1 C21 1.464(3) . ?
C10 C11 1.382(3) . ?
C10 C15 1.386(3) . ?
C10 C9 1.487(3) . ?
C8 C9 1.348(3) . ?
C8 C6 1.479(3) . ?
C9 C17 1.472(3) . ?
C6 C1 1.392(3) . ?
C6 C5 1.395(3) . ?
C15 C14 1.375(3) . ?
C15 H15 0.9300 . ?
C17 C20 1.364(3) . ?
C17 C18 1.424(3) . ?
C5 C4 1.388(3) . ?
C5 H5 0.9300 . ?
C1 C2 1.382(3) . ?
C14 C13 1.376(3) . ?
C14 H14 0.9300 . ?
C11 C12 1.383(3) . ?
C11 H11 0.9300 . ?
C13 C12 1.374(4) . ?
C13 C16 1.511(3) . ?
C2 C3 1.367(4) . ?
C2 H2 0.9300 . ?
C4 C3 1.389(4) . ?
C4 C7 1.507(4) . ?
C3 H3 0.9300 . ?
C20 H20 0.9300 . ?
C12 H12 0.9300 . ?
C18 C19 1.379(4) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
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 116.75(13) . . ?
O2 S1 N1 110.38(11) . . ?
O1 S1 N1 110.55(12) . . ?
O2 S1 C1 113.31(12) . . ?
O1 S1 C1 109.62(12) . . ?
N1 S1 C1 93.92(10) . . ?
C19 S2 C20 92.06(13) . . ?
C8 N1 C21 121.1(2) . . ?
C8 N1 S1 113.10(15) . . ?
C21 N1 S1 118.86(17) . . ?
C11 C10 C15 117.6(2) . . ?
C11 C10 C9 121.3(2) . . ?
C15 C10 C9 121.0(2) . . ?
C9 C8 N1 121.75(19) . . ?
C9 C8 C6 128.9(2) . . ?
N1 C8 C6 108.72(18) . . ?
C8 C9 C17 123.5(2) . . ?
C8 C9 C10 119.40(19) . . ?
C17 C9 C10 116.95(19) . . ?
C1 C6 C5 117.0(2) . . ?
C1 C6 C8 111.69(19) . . ?
C5 C6 C8 130.9(2) . . ?
C14 C15 C10 120.8(2) . . ?
C14 C15 H15 119.6 . . ?
C10 C15 H15 119.6 . . ?
C20 C17 C18 110.3(2) . . ?
C20 C17 C9 124.0(2) . . ?
C18 C17 C9 125.5(2) . . ?
C4 C5 C6 120.6(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C2 C1 C6 123.4(2) . . ?
C2 C1 S1 125.42(19) . . ?
C6 C1 S1 110.99(17) . . ?
C15 C14 C13 121.7(2) . . ?
C15 C14 H14 119.1 . . ?
C13 C14 H14 119.1 . . ?
C10 C11 C12 120.8(2) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C12 C13 C14 117.5(2) . . ?
C12 C13 C16 121.1(2) . . ?
C14 C13 C16 121.5(2) . . ?
C3 C2 C1 117.8(2) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C5 C4 C3 119.7(2) . . ?
C5 C4 C7 119.6(3) . . ?
C3 C4 C7 120.8(2) . . ?
C2 C3 C4 121.4(2) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C17 C20 S2 112.98(19) . . ?
C17 C20 H20 123.5 . . ?
S2 C20 H20 123.5 . . ?
C13 C12 C11 121.5(2) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C19 C18 C17 112.6(2) . . ?
C19 C18 H18 123.7 . . ?
C17 C18 H18 123.7 . . ?
C18 C19 S2 112.0(2) . . ?
C18 C19 H19 124.0 . . ?
S2 C19 H19 124.0 . . ?
N1 C21 H21A 109.5 . . ?
N1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
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 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.442
_refine_diff_density_rms         0.044
_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_Compound3ad
_database_code_depnum_ccdc_archive 'CCDC 2082517'
loop_
_audit_author_name
_audit_author_address
'K C Kumara Swamy'
;University of Hyderabad
India
;
_audit_update_record             
;
2021-05-08 deposited with the CCDC.	2021-07-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H18 Cl N O2 S'
_chemical_formula_weight         395.88

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           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   10.0494(11)
_cell_length_b                   10.1081(10)
_cell_length_c                   10.9713(10)
_cell_angle_alpha                104.997(3)
_cell_angle_beta                 112.432(3)
_cell_angle_gamma                95.785(4)
_cell_volume                     969.88(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    9862
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      26.39

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             412
_exptl_absorpt_coefficient_mu    0.321
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(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_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            35324
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_sigmaI/netI    0.0140
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.25
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3388
_reflns_number_gt                2977
_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, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0422P)²+0.4096P] 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       0.036(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3388
_refine_ls_number_parameters     247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0343
_refine_ls_wR_factor_ref         0.0918
_refine_ls_wR_factor_gt          0.0882
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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 0.25917(6) 0.64120(5) 0.63997(5) 0.04661(17) Uani 1 1 d . . .
Cl1 Cl 0.16421(6) -0.17941(6) 0.00008(5) 0.06087(19) Uani 1 1 d . . .
O2 O 0.13624(19) 0.69702(15) 0.64872(17) 0.0680(4) Uani 1 1 d . . .
N1 N 0.24202(17) 0.48060(15) 0.64946(14) 0.0422(4) Uani 1 1 d . . .
O1 O 0.40287(19) 0.72526(16) 0.73470(15) 0.0716(5) Uani 1 1 d . . .
C10 C 0.24597(18) 0.13749(16) 0.40984(17) 0.0342(4) Uani 1 1 d . . .
C9 C 0.27237(18) 0.25057(17) 0.54053(17) 0.0351(4) Uani 1 1 d . . .
C8 C 0.25107(18) 0.37967(17) 0.53644(16) 0.0360(4) Uani 1 1 d . . .
C6 C 0.24151(18) 0.44408(17) 0.42735(17) 0.0367(4) Uani 1 1 d . . .
C16 C 0.32054(18) 0.21290(17) 0.67043(17) 0.0358(4) Uani 1 1 d . . .
C13 C 0.1960(2) -0.06075(18) 0.16095(17) 0.0406(4) Uani 1 1 d . . .
C17 C 0.43167(19) 0.30549(19) 0.79451(18) 0.0434(4) Uani 1 1 d . . .
H17 H 0.4762 0.3912 0.7954 0.052 Uiso 1 1 calc R . .
C11 C 0.10423(19) 0.08012(19) 0.30668(18) 0.0427(4) Uani 1 1 d . . .
H11 H 0.0250 0.1091 0.3211 0.051 Uiso 1 1 calc R . .
C21 C 0.2593(2) 0.08419(18) 0.67263(19) 0.0429(4) Uani 1 1 d . . .
H21 H 0.1872 0.0194 0.5907 0.051 Uiso 1 1 calc R . .
C12 C 0.0784(2) -0.01983(19) 0.18220(19) 0.0456(4) Uani 1 1 d . . .
H12 H -0.0175 -0.0587 0.1139 0.055 Uiso 1 1 calc R . .
C1 C 0.24536(19) 0.58680(18) 0.47152(18) 0.0395(4) Uani 1 1 d . . .
C18 C 0.4764(2) 0.2715(2) 0.91595(19) 0.0504(5) Uani 1 1 d . . .
H18 H 0.5507 0.3344 0.9978 0.060 Uiso 1 1 calc R . .
C15 C 0.3615(2) 0.0889(2) 0.38752(19) 0.0483(5) Uani 1 1 d . . .
H15 H 0.4570 0.1228 0.4578 0.058 Uiso 1 1 calc R . .
C5 C 0.2360(2) 0.38643(19) 0.29498(18) 0.0457(4) Uani 1 1 d . . .
H5 H 0.2375 0.2921 0.2634 0.055 Uiso 1 1 calc R . .
C20 C 0.3041(2) 0.0510(2) 0.7950(2) 0.0493(5) Uani 1 1 d . . .
H20 H 0.2612 -0.0350 0.7947 0.059 Uiso 1 1 calc R . .
C14 C 0.3376(2) -0.0089(2) 0.2628(2) 0.0507(5) Uani 1 1 d . . .
H14 H 0.4163 -0.0391 0.2481 0.061 Uiso 1 1 calc R . .
C22 C 0.1516(2) 0.4420(2) 0.7174(2) 0.0537(5) Uani 1 1 d . . .
H22A H 0.0797 0.3564 0.6570 0.080 Uiso 1 1 calc R . .
H22B H 0.1021 0.5156 0.7372 0.080 Uiso 1 1 calc R . .
H22C H 0.2135 0.4286 0.8028 0.080 Uiso 1 1 calc R . .
C19 C 0.4118(2) 0.1448(2) 0.9168(2) 0.0512(5) Uani 1 1 d . . .
H19 H 0.4409 0.1231 0.9992 0.061 Uiso 1 1 calc R . .
C4 C 0.2283(2) 0.4684(2) 0.21023(19) 0.0504(5) Uani 1 1 d . . .
C2 C 0.2418(2) 0.6723(2) 0.3907(2) 0.0495(5) Uani 1 1 d . . .
H2 H 0.2464 0.7678 0.4241 0.059 Uiso 1 1 calc R . .
C3 C 0.2313(2) 0.6107(2) 0.2592(2) 0.0534(5) Uani 1 1 d . . .
H3 H 0.2260 0.6652 0.2017 0.064 Uiso 1 1 calc R . .
C7 C 0.2149(3) 0.4034(3) 0.0652(2) 0.0776(7) Uani 1 1 d . . .
H7A H 0.2627 0.3257 0.0625 0.116 Uiso 1 1 calc R . .
H7B H 0.2611 0.4722 0.0391 0.116 Uiso 1 1 calc R . .
H7C H 0.1124 0.3706 0.0013 0.116 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 1.4275(16) . ?
S1 O2 1.4341(15) . ?
S1 N1 1.6494(15) . ?
S1 C1 1.7321(17) . ?
Cl1 C13 1.7471(17) . ?
N1 C8 1.427(2) . ?
N1 C22 1.460(2) . ?
C10 C11 1.382(2) . ?
C10 C15 1.385(2) . ?
C10 C9 1.494(2) . ?
C9 C8 1.353(2) . ?
C9 C16 1.484(2) . ?
C8 C6 1.481(2) . ?
C6 C1 1.389(2) . ?
C6 C5 1.395(2) . ?
C16 C21 1.392(2) . ?
C16 C17 1.395(2) . ?
C13 C14 1.372(3) . ?
C13 C12 1.372(3) . ?
C17 C18 1.381(3) . ?
C17 H17 0.9300 . ?
C11 C12 1.384(2) . ?
C11 H11 0.9300 . ?
C21 C20 1.385(3) . ?
C21 H21 0.9300 . ?
C12 H12 0.9300 . ?
C1 C2 1.383(2) . ?
C18 C19 1.380(3) . ?
C18 H18 0.9300 . ?
C15 C14 1.382(3) . ?
C15 H15 0.9300 . ?
C5 C4 1.384(3) . ?
C5 H5 0.9300 . ?
C20 C19 1.374(3) . ?
C20 H20 0.9300 . ?
C14 H14 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C19 H19 0.9300 . ?
C4 C3 1.392(3) . ?
C4 C7 1.503(3) . ?
C2 C3 1.373(3) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
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 116.61(10) . . ?
O1 S1 N1 111.01(9) . . ?
O2 S1 N1 109.89(9) . . ?
O1 S1 C1 110.57(9) . . ?
O2 S1 C1 112.72(9) . . ?
N1 S1 C1 93.73(7) . . ?
C8 N1 C22 121.34(15) . . ?
C8 N1 S1 113.27(11) . . ?
C22 N1 S1 117.76(12) . . ?
C11 C10 C15 118.28(15) . . ?
C11 C10 C9 120.24(15) . . ?
C15 C10 C9 121.47(15) . . ?
C8 C9 C16 123.14(14) . . ?
C8 C9 C10 120.00(14) . . ?
C16 C9 C10 116.86(13) . . ?
C9 C8 N1 121.96(14) . . ?
C9 C8 C6 129.08(14) . . ?
N1 C8 C6 108.89(13) . . ?
C1 C6 C5 117.32(15) . . ?
C1 C6 C8 111.90(14) . . ?
C5 C6 C8 130.71(15) . . ?
C21 C16 C17 117.80(16) . . ?
C21 C16 C9 121.65(15) . . ?
C17 C16 C9 120.53(15) . . ?
C14 C13 C12 121.23(16) . . ?
C14 C13 Cl1 119.67(14) . . ?
C12 C13 Cl1 119.09(14) . . ?
C18 C17 C16 120.84(17) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C10 C11 C12 121.04(16) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C20 C21 C16 121.04(17) . . ?
C20 C21 H21 119.5 . . ?
C16 C21 H21 119.5 . . ?
C13 C12 C11 119.13(16) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C2 C1 C6 123.45(16) . . ?
C2 C1 S1 125.59(14) . . ?
C6 C1 S1 110.94(13) . . ?
C19 C18 C17 120.50(18) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C14 C15 C10 121.26(17) . . ?
C14 C15 H15 119.4 . . ?
C10 C15 H15 119.4 . . ?
C4 C5 C6 120.53(17) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C19 C20 C21 120.28(18) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C13 C14 C15 118.95(17) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
N1 C22 H22A 109.5 . . ?
N1 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N1 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C19 C18 119.50(17) . . ?
C20 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
C5 C4 C3 119.77(17) . . ?
C5 C4 C7 119.98(19) . . ?
C3 C4 C7 120.25(18) . . ?
C3 C2 C1 117.49(17) . . ?
C3 C2 H2 121.3 . . ?
C1 C2 H2 121.3 . . ?
C2 C3 C4 121.37(17) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
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 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.034
_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_Compound4mh
_database_code_depnum_ccdc_archive 'CCDC 2082519'
loop_
_audit_author_name
_audit_author_address
'K C Kumara Swamy'
;University of Hyderabad
India
;
_audit_update_record             
;
2021-05-08 deposited with the CCDC.	2021-07-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H21 N O2 S'
_chemical_formula_weight         339.44

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   'P 1 21/c 1'

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                   20.5737(8)
_cell_length_b                   6.0343(2)
_cell_length_c                   14.7085(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.444(4)
_cell_angle_gamma                90.00
_cell_volume                     1768.31(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5014
_cell_measurement_theta_min      2.0420
_cell_measurement_theta_max      24.3280

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_type   NONE
_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       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14039
_diffrn_reflns_av_R_equivalents  0.0663
_diffrn_reflns_av_sigmaI/netI    0.0585
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.04
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3112
_reflns_number_gt                1967
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0761P)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       0.0031(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3112
_refine_ls_number_parameters     220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0901
_refine_ls_R_factor_gt           0.0555
_refine_ls_wR_factor_ref         0.1692
_refine_ls_wR_factor_gt          0.1453
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.17771(4) 0.94153(11) 0.48212(6) 0.0629(3) Uani 1 1 d . . .
N1 N 0.21026(10) 0.7500(3) 0.42926(16) 0.0520(6) Uani 1 1 d . . .
O2 O 0.23213(10) 1.0643(3) 0.53855(18) 0.0827(8) Uani 1 1 d . . .
O1 O 0.12648(10) 1.0553(3) 0.41469(17) 0.0862(8) Uani 1 1 d . . .
C7 C 0.24838(12) 0.5762(4) 0.59223(19) 0.0413(6) Uani 1 1 d . . .
C12 C 0.36858(12) 0.4990(4) 0.64809(18) 0.0443(7) Uani 1 1 d . . .
C6 C 0.17794(12) 0.6004(4) 0.59813(18) 0.0424(7) Uani 1 1 d . . .
C8 C 0.30010(12) 0.5262(4) 0.66433(19) 0.0459(7) Uani 1 1 d . . .
C1 C 0.13992(13) 0.7773(4) 0.55299(19) 0.0493(7) Uani 1 1 d . . .
C4 C 0.07903(13) 0.4769(5) 0.6464(2) 0.0538(8) Uani 1 1 d . . .
C5 C 0.14542(12) 0.4502(4) 0.64319(18) 0.0480(7) Uani 1 1 d . . .
H5 H 0.1690 0.3272 0.6723 0.058 Uiso 1 1 calc R . .
C13 C 0.38570(13) 0.3107(4) 0.6070(2) 0.0562(8) Uani 1 1 d . . .
H13 H 0.3549 0.1957 0.5909 0.067 Uiso 1 1 calc R . .
C18 C 0.26147(13) 0.6164(5) 0.49580(19) 0.0579(8) Uani 1 1 d . . .
H18A H 0.3045 0.6902 0.5047 0.069 Uiso 1 1 calc R . .
H18B H 0.2651 0.4738 0.4671 0.069 Uiso 1 1 calc R . .
C17 C 0.41599(14) 0.6648(5) 0.6726(2) 0.0614(8) Uani 1 1 d . . .
H17 H 0.4055 0.7932 0.7009 0.074 Uiso 1 1 calc R . .
C3 C 0.04407(14) 0.6587(5) 0.6019(2) 0.0650(9) Uani 1 1 d . . .
H3 H -0.0003 0.6803 0.6041 0.078 Uiso 1 1 calc R . .
C2 C 0.07407(14) 0.8081(5) 0.5544(2) 0.0624(9) Uani 1 1 d . . .
H2 H 0.0500 0.9284 0.5237 0.075 Uiso 1 1 calc R . .
C14 C 0.44858(15) 0.2908(6) 0.5894(2) 0.0718(9) Uani 1 1 d . . .
H14 H 0.4594 0.1640 0.5603 0.086 Uiso 1 1 calc R . .
C20 C 0.04519(14) 0.3089(5) 0.6959(2) 0.0743(10) Uani 1 1 d . . .
H20A H 0.0712 0.1750 0.7061 0.111 Uiso 1 1 calc R . .
H20B H 0.0011 0.2772 0.6577 0.111 Uiso 1 1 calc R . .
H20C H 0.0418 0.3680 0.7551 0.111 Uiso 1 1 calc R . .
C15 C 0.49457(15) 0.4562(6) 0.6144(2) 0.0737(10) Uani 1 1 d . . .
H15 H 0.5369 0.4416 0.6032 0.088 Uiso 1 1 calc R . .
C19 C 0.16264(15) 0.6193(5) 0.3581(2) 0.0749(10) Uani 1 1 d . . .
H19A H 0.1861 0.5489 0.3172 0.112 Uiso 1 1 calc R . .
H19B H 0.1286 0.7153 0.3221 0.112 Uiso 1 1 calc R . .
H19C H 0.1422 0.5084 0.3886 0.112 Uiso 1 1 calc R . .
C9 C 0.29383(14) 0.4977(6) 0.7611(2) 0.0758(10) Uani 1 1 d . . .
H9 H 0.2524 0.5584 0.7727 0.091 Uiso 1 1 calc R . .
C16 C 0.47851(15) 0.6432(6) 0.6559(3) 0.0754(10) Uani 1 1 d . . .
H16 H 0.5099 0.7563 0.6729 0.090 Uiso 1 1 calc R . .
C11 C 0.35233(16) 0.4974(8) 0.8449(2) 0.1027(14) Uani 1 1 d . . .
H11A H 0.3966 0.5181 0.8343 0.123 Uiso 1 1 calc R . .
H11B H 0.3462 0.5630 0.9023 0.123 Uiso 1 1 calc R . .
C10 C 0.3180(2) 0.2907(9) 0.8140(3) 0.1301(17) Uani 1 1 d . . .
H10A H 0.2905 0.2277 0.8523 0.156 Uiso 1 1 calc R . .
H10B H 0.3410 0.1828 0.7843 0.156 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 1.4240(19) . ?
S1 O1 1.4299(18) . ?
S1 N1 1.627(2) . ?
S1 C1 1.754(3) . ?
N1 C19 1.472(3) . ?
N1 C18 1.484(3) . ?
C7 C8 1.336(3) . ?
C7 C6 1.480(3) . ?
C7 C18 1.528(4) . ?
C12 C13 1.373(3) . ?
C12 C17 1.381(3) . ?
C12 C8 1.496(3) . ?
C6 C5 1.389(3) . ?
C6 C1 1.390(3) . ?
C8 C9 1.472(4) . ?
C1 C2 1.373(4) . ?
C4 C3 1.384(4) . ?
C4 C5 1.388(3) . ?
C4 C20 1.515(4) . ?
C5 H5 0.9300 . ?
C13 C14 1.387(4) . ?
C13 H13 0.9300 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C17 C16 1.375(4) . ?
C17 H17 0.9300 . ?
C3 C2 1.377(4) . ?
C3 H3 0.9300 . ?
C2 H2 0.9300 . ?
C14 C15 1.361(4) . ?
C14 H14 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C15 C16 1.362(4) . ?
C15 H15 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C9 C10 1.490(4) . ?
C9 C11 1.492(4) . ?
C9 H9 0.9800 . ?
C16 H16 0.9300 . ?
C11 C10 1.449(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 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 119.39(13) . . ?
O2 S1 N1 106.90(12) . . ?
O1 S1 N1 109.24(13) . . ?
O2 S1 C1 110.38(14) . . ?
O1 S1 C1 108.91(13) . . ?
N1 S1 C1 100.30(12) . . ?
C19 N1 C18 114.5(2) . . ?
C19 N1 S1 116.12(18) . . ?
C18 N1 S1 112.31(18) . . ?
C8 C7 C6 125.0(2) . . ?
C8 C7 C18 118.9(2) . . ?
C6 C7 C18 116.1(2) . . ?
C13 C12 C17 118.2(2) . . ?
C13 C12 C8 121.1(2) . . ?
C17 C12 C8 120.7(2) . . ?
C5 C6 C1 116.6(2) . . ?
C5 C6 C7 124.0(2) . . ?
C1 C6 C7 119.4(2) . . ?
C7 C8 C9 123.3(2) . . ?
C7 C8 C12 119.6(2) . . ?
C9 C8 C12 117.1(2) . . ?
C2 C1 C6 122.4(3) . . ?
C2 C1 S1 121.2(2) . . ?
C6 C1 S1 115.9(2) . . ?
C3 C4 C5 118.4(3) . . ?
C3 C4 C20 120.7(3) . . ?
C5 C4 C20 120.8(3) . . ?
C4 C5 C6 122.4(3) . . ?
C4 C5 H5 118.8 . . ?
C6 C5 H5 118.8 . . ?
C12 C13 C14 120.5(3) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
N1 C18 C7 116.0(2) . . ?
N1 C18 H18A 108.3 . . ?
C7 C18 H18A 108.3 . . ?
N1 C18 H18B 108.3 . . ?
C7 C18 H18B 108.3 . . ?
H18A C18 H18B 107.4 . . ?
C16 C17 C12 121.0(3) . . ?
C16 C17 H17 119.5 . . ?
C12 C17 H17 119.5 . . ?
C2 C3 C4 120.9(3) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C1 C2 C3 119.2(3) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C15 C14 C13 120.3(3) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
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 . . ?
C14 C15 C16 119.9(3) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
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 . . ?
C8 C9 C10 120.3(3) . . ?
C8 C9 C11 123.5(3) . . ?
C10 C9 C11 58.2(2) . . ?
C8 C9 H9 114.5 . . ?
C10 C9 H9 114.5 . . ?
C11 C9 H9 114.5 . . ?
C15 C16 C17 120.1(3) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C10 C11 C9 60.9(2) . . ?
C10 C11 H11A 117.7 . . ?
C9 C11 H11A 117.7 . . ?
C10 C11 H11B 117.7 . . ?
C9 C11 H11B 117.7 . . ?
H11A C11 H11B 114.8 . . ?
C11 C10 C9 61.0(2) . . ?
C11 C10 H10A 117.7 . . ?
C9 C10 H10A 117.7 . . ?
C11 C10 H10B 117.7 . . ?
C9 C10 H10B 117.7 . . ?
H10A C10 H10B 114.8 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.045
_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_Compound3ba
_database_code_depnum_ccdc_archive 'CCDC 2082516'
loop_
_audit_author_name
_audit_author_address
'K C Kumara Swamy'
;University of Hyderabad
India
;
_audit_update_record             
;
2021-05-08 deposited with the CCDC.	2021-07-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C46 H42 N2 O4 S2'
_chemical_formula_weight         750.94

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                   9.9875(2)
_cell_length_b                   14.1732(3)
_cell_length_c                   14.8341(3)
_cell_angle_alpha                83.860(2)
_cell_angle_beta                 80.349(2)
_cell_angle_gamma                74.882(2)
_cell_volume                     1994.06(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    11221
_cell_measurement_theta_min      1.9670
_cell_measurement_theta_max      25.4210

_exptl_crystal_description       blocks
_exptl_crystal_colour            colorless
_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    1.251
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.40985
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)'

_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       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            29120
_diffrn_reflns_av_R_equivalents  0.0685
_diffrn_reflns_av_sigmaI/netI    0.0600
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.97
_diffrn_reflns_theta_max         25.00
_reflns_number_total             7013
_reflns_number_gt                4548
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0685P)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       0.0029(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         7013
_refine_ls_number_parameters     494
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0852
_refine_ls_R_factor_gt           0.0543
_refine_ls_wR_factor_ref         0.1546
_refine_ls_wR_factor_gt          0.1371
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_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 0.05605(6) 0.32339(5) 0.54407(5) 0.0593(2) Uani 1 1 d . . .
S1 S 0.83932(7) 0.20610(5) 0.94458(5) 0.0603(2) Uani 1 1 d . . .
O4 O -0.03260(17) 0.38707(13) 0.61022(14) 0.0804(6) Uani 1 1 d . . .
O2 O 0.8199(2) 0.13748(13) 0.88722(14) 0.0843(6) Uani 1 1 d . . .
N1 N 0.8395(2) 0.31032(14) 0.88653(14) 0.0567(6) Uani 1 1 d . . .
O3 O 0.0023(2) 0.32369(18) 0.46122(13) 0.1005(8) Uani 1 1 d . . .
N2 N 0.09980(19) 0.21136(14) 0.59141(15) 0.0604(6) Uani 1 1 d . . .
O1 O 0.74416(19) 0.22083(17) 1.02834(13) 0.0974(7) Uani 1 1 d . . .
C15 C 0.8545(3) 0.51614(17) 0.83294(18) 0.0514(6) Uani 1 1 d . . .
C24 C 0.2263(2) 0.33588(17) 0.52288(17) 0.0490(6) Uani 1 1 d . . .
C8 C 0.9760(2) 0.43345(17) 0.85062(16) 0.0504(6) Uani 1 1 d . . .
C1 C 1.0117(2) 0.18532(18) 0.96284(17) 0.0535(7) Uani 1 1 d . . .
C32 C 0.2288(2) 0.00799(17) 0.65978(17) 0.0501(6) Uani 1 1 d . . .
C30 C 0.2462(2) 0.17574(17) 0.59713(17) 0.0494(6) Uani 1 1 d . . .
C9 C 1.1148(3) 0.45708(18) 0.82685(17) 0.0524(6) Uani 1 1 d . . .
C7 C 0.9645(2) 0.34306(18) 0.88243(16) 0.0489(6) Uani 1 1 d . . .
C29 C 0.3185(2) 0.25142(16) 0.55213(17) 0.0487(6) Uani 1 1 d . . .
C6 C 1.0676(2) 0.26330(17) 0.92588(16) 0.0496(6) Uani 1 1 d . . .
C31 C 0.3032(2) 0.08689(17) 0.63494(16) 0.0508(6) Uani 1 1 d . . .
C33 C 0.1653(3) -0.02393(18) 0.59664(18) 0.0579(7) Uani 1 1 d . . .
H33 H 0.1688 0.0048 0.5372 0.070 Uiso 1 1 calc R . .
C39 C 0.4480(2) 0.06177(18) 0.65968(17) 0.0526(6) Uani 1 1 d . . .
C16 C 0.7335(3) 0.53857(18) 0.89789(18) 0.0602(7) Uani 1 1 d . . .
H16 H 0.7288 0.5018 0.9536 0.072 Uiso 1 1 calc R . .
C28 C 0.4614(2) 0.24692(18) 0.53101(18) 0.0583(7) Uani 1 1 d . . .
H28 H 0.5265 0.1901 0.5468 0.070 Uiso 1 1 calc R . .
C20 C 0.8590(3) 0.57481(18) 0.75268(18) 0.0580(7) Uani 1 1 d . . .
H20 H 0.9389 0.5627 0.7090 0.070 Uiso 1 1 calc R . .
C40 C 0.5483(3) -0.01800(18) 0.62456(18) 0.0606(7) Uani 1 1 d . . .
H40 H 0.5259 -0.0554 0.5841 0.073 Uiso 1 1 calc R . .
C18 C 0.6252(3) 0.67146(19) 0.79848(19) 0.0594(7) Uani 1 1 d . . .
C14 C 1.1440(3) 0.53084(18) 0.86859(18) 0.0605(7) Uani 1 1 d . . .
H14 H 1.0770 0.5648 0.9129 0.073 Uiso 1 1 calc R . .
C25 C 0.2687(3) 0.41622(18) 0.47744(18) 0.0619(7) Uani 1 1 d . . .
H25 H 0.2041 0.4720 0.4587 0.074 Uiso 1 1 calc R . .
C17 C 0.6216(3) 0.61469(19) 0.87977(19) 0.0644(7) Uani 1 1 d . . .
H17 H 0.5418 0.6281 0.9234 0.077 Uiso 1 1 calc R . .
C19 C 0.7464(3) 0.65112(18) 0.73655(18) 0.0624(7) Uani 1 1 d . . .
H19 H 0.7523 0.6901 0.6822 0.075 Uiso 1 1 calc R . .
C37 C 0.2242(3) -0.0393(2) 0.74607(19) 0.0650(8) Uani 1 1 d . . .
H37 H 0.2686 -0.0214 0.7895 0.078 Uiso 1 1 calc R . .
C35 C 0.0896(3) -0.14340(19) 0.7076(2) 0.0619(7) Uani 1 1 d . . .
C5 C 1.2049(3) 0.25713(19) 0.93861(18) 0.0610(7) Uani 1 1 d . . .
H5 H 1.2450 0.3090 0.9167 0.073 Uiso 1 1 calc R . .
C26 C 0.4104(3) 0.41009(19) 0.46114(18) 0.0639(7) Uani 1 1 d . . .
H26 H 0.4416 0.4636 0.4323 0.077 Uiso 1 1 calc R . .
C34 C 0.0965(3) -0.0984(2) 0.6211(2) 0.0646(7) Uani 1 1 d . . .
H34 H 0.0540 -0.1182 0.5777 0.078 Uiso 1 1 calc R . .
C27 C 0.5075(3) 0.32687(19) 0.48640(19) 0.0608(7) Uani 1 1 d . . .
C10 C 1.2152(3) 0.4100(2) 0.75973(19) 0.0688(8) Uani 1 1 d . . .
H10 H 1.1965 0.3617 0.7295 0.083 Uiso 1 1 calc R . .
C2 C 1.0852(3) 0.10437(19) 1.01063(19) 0.0687(8) Uani 1 1 d . . .
H2 H 1.0432 0.0545 1.0365 0.082 Uiso 1 1 calc R . .
C4 C 1.2829(3) 0.1756(2) 0.9832(2) 0.0646(8) Uani 1 1 d . . .
C3 C 1.2213(3) 0.0997(2) 1.0187(2) 0.0748(9) Uani 1 1 d . . .
H3 H 1.2734 0.0448 1.0486 0.090 Uiso 1 1 calc R . .
C22 C 0.7378(3) 0.34449(19) 0.82178(19) 0.0687(8) Uani 1 1 d . . .
H22A H 0.6571 0.3905 0.8501 0.103 Uiso 1 1 calc R . .
H22B H 0.7098 0.2896 0.8051 0.103 Uiso 1 1 calc R . .
H22C H 0.7801 0.3757 0.7679 0.103 Uiso 1 1 calc R . .
C36 C 0.1551(3) -0.1123(2) 0.7688(2) 0.0706(8) Uani 1 1 d . . .
H36 H 0.1525 -0.1419 0.8279 0.085 Uiso 1 1 calc R . .
C13 C 1.2714(3) 0.5543(2) 0.8450(2) 0.0733(8) Uani 1 1 d . . .
H13 H 1.2899 0.6035 0.8740 0.088 Uiso 1 1 calc R . .
C41 C 0.6812(3) -0.0428(2) 0.6488(2) 0.0762(9) Uani 1 1 d . . .
H41 H 0.7479 -0.0961 0.6240 0.091 Uiso 1 1 calc R . .
C44 C 0.4825(3) 0.1137(2) 0.7221(2) 0.0755(8) Uani 1 1 d . . .
H44 H 0.4154 0.1659 0.7485 0.091 Uiso 1 1 calc R . .
C12 C 1.3717(3) 0.5053(2) 0.7787(2) 0.0802(9) Uani 1 1 d . . .
H12 H 1.4576 0.5213 0.7629 0.096 Uiso 1 1 calc R . .
C21 C 0.5013(3) 0.7531(2) 0.7771(2) 0.0860(10) Uani 1 1 d . . .
H21A H 0.4243 0.7541 0.8257 0.129 Uiso 1 1 calc R . .
H21B H 0.4743 0.7426 0.7206 0.129 Uiso 1 1 calc R . .
H21C H 0.5265 0.8146 0.7715 0.129 Uiso 1 1 calc R . .
C38 C 0.0153(3) -0.2237(2) 0.7348(2) 0.0948(10) Uani 1 1 d . . .
H38A H -0.0365 -0.2285 0.6873 0.142 Uiso 1 1 calc R . .
H38B H -0.0479 -0.2092 0.7907 0.142 Uiso 1 1 calc R . .
H38C H 0.0829 -0.2847 0.7439 0.142 Uiso 1 1 calc R . .
C42 C 0.7151(3) 0.0104(3) 0.7088(2) 0.0884(10) Uani 1 1 d . . .
H42 H 0.8050 -0.0063 0.7247 0.106 Uiso 1 1 calc R . .
C11 C 1.3431(3) 0.4332(2) 0.7365(2) 0.0818(9) Uani 1 1 d . . .
H11 H 1.4101 0.3996 0.6920 0.098 Uiso 1 1 calc R . .
C46 C 0.6620(3) 0.3212(2) 0.4657(2) 0.0938(11) Uani 1 1 d . . .
H46A H 0.6759 0.3832 0.4387 0.141 Uiso 1 1 calc R . .
H46B H 0.7063 0.2713 0.4237 0.141 Uiso 1 1 calc R . .
H46C H 0.7024 0.3054 0.5214 0.141 Uiso 1 1 calc R . .
C43 C 0.6163(3) 0.0887(3) 0.7458(2) 0.0899(10) Uani 1 1 d . . .
H43 H 0.6392 0.1251 0.7869 0.108 Uiso 1 1 calc R . .
C23 C 1.4323(3) 0.1681(2) 0.9935(2) 0.0937(11) Uani 1 1 d . . .
H23A H 1.4575 0.2275 0.9685 0.141 Uiso 1 1 calc R . .
H23B H 1.4925 0.1138 0.9613 0.141 Uiso 1 1 calc R . .
H23C H 1.4426 0.1580 1.0572 0.141 Uiso 1 1 calc R . .
C45 C -0.0090(3) 0.1847(2) 0.6620(2) 0.1047(12) Uani 1 1 d . . .
H45A H -0.0205 0.1219 0.6510 0.157 Uiso 1 1 calc R . .
H45B H -0.0960 0.2331 0.6596 0.157 Uiso 1 1 calc R . .
H45C H 0.0186 0.1816 0.7214 0.157 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 O3 1.4206(18) . ?
S2 O4 1.4292(17) . ?
S2 N2 1.645(2) . ?
S2 C24 1.728(2) . ?
S1 O2 1.4275(18) . ?
S1 O1 1.4307(19) . ?
S1 N1 1.629(2) . ?
S1 C1 1.732(2) . ?
N1 C7 1.431(3) . ?
N1 C22 1.470(3) . ?
N2 C30 1.431(3) . ?
N2 C45 1.473(3) . ?
C15 C20 1.379(3) . ?
C15 C16 1.401(3) . ?
C15 C8 1.488(3) . ?
C24 C29 1.384(3) . ?
C24 C25 1.386(3) . ?
C8 C7 1.344(3) . ?
C8 C9 1.487(3) . ?
C1 C2 1.385(3) . ?
C1 C6 1.387(3) . ?
C32 C37 1.379(3) . ?
C32 C33 1.387(3) . ?
C32 C31 1.481(3) . ?
C30 C31 1.344(3) . ?
C30 C29 1.485(3) . ?
C9 C10 1.379(3) . ?
C9 C14 1.386(3) . ?
C7 C6 1.488(3) . ?
C29 C28 1.395(3) . ?
C6 C5 1.394(3) . ?
C31 C39 1.495(3) . ?
C33 C34 1.390(3) . ?
C33 H33 0.9300 . ?
C39 C44 1.379(3) . ?
C39 C40 1.383(3) . ?
C16 C17 1.377(3) . ?
C16 H16 0.9300 . ?
C28 C27 1.394(3) . ?
C28 H28 0.9300 . ?
C20 C19 1.376(3) . ?
C20 H20 0.9300 . ?
C40 C41 1.380(3) . ?
C40 H40 0.9300 . ?
C18 C19 1.376(3) . ?
C18 C17 1.377(3) . ?
C18 C21 1.509(3) . ?
C14 C13 1.377(3) . ?
C14 H14 0.9300 . ?
C25 C26 1.376(3) . ?
C25 H25 0.9300 . ?
C17 H17 0.9300 . ?
C19 H19 0.9300 . ?
C37 C36 1.372(3) . ?
C37 H37 0.9300 . ?
C35 C34 1.369(3) . ?
C35 C36 1.371(3) . ?
C35 C38 1.500(4) . ?
C5 C4 1.385(3) . ?
C5 H5 0.9300 . ?
C26 C27 1.379(3) . ?
C26 H26 0.9300 . ?
C34 H34 0.9300 . ?
C27 C46 1.505(3) . ?
C10 C11 1.380(3) . ?
C10 H10 0.9300 . ?
C2 C3 1.368(3) . ?
C2 H2 0.9300 . ?
C4 C3 1.389(4) . ?
C4 C23 1.500(3) . ?
C3 H3 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C36 H36 0.9300 . ?
C13 C12 1.381(4) . ?
C13 H13 0.9300 . ?
C41 C42 1.362(4) . ?
C41 H41 0.9300 . ?
C44 C43 1.386(4) . ?
C44 H44 0.9300 . ?
C12 C11 1.367(4) . ?
C12 H12 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C42 C43 1.372(4) . ?
C42 H42 0.9300 . ?
C11 H11 0.9300 . ?
C46 H46A 0.9600 . ?
C46 H46B 0.9600 . ?
C46 H46C 0.9600 . ?
C43 H43 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C45 H45A 0.9600 . ?
C45 H45B 0.9600 . ?
C45 H45C 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
O3 S2 O4 115.63(13) . . ?
O3 S2 N2 110.68(13) . . ?
O4 S2 N2 109.69(11) . . ?
O3 S2 C24 111.37(12) . . ?
O4 S2 C24 113.38(12) . . ?
N2 S2 C24 94.01(11) . . ?
O2 S1 O1 116.11(14) . . ?
O2 S1 N1 110.04(11) . . ?
O1 S1 N1 110.47(13) . . ?
O2 S1 C1 112.72(12) . . ?
O1 S1 C1 111.60(12) . . ?
N1 S1 C1 93.66(11) . . ?
C7 N1 C22 124.5(2) . . ?
C7 N1 S1 115.11(15) . . ?
C22 N1 S1 117.33(16) . . ?
C30 N2 C45 122.4(2) . . ?
C30 N2 S2 114.14(16) . . ?
C45 N2 S2 114.65(16) . . ?
C20 C15 C16 117.8(2) . . ?
C20 C15 C8 120.8(2) . . ?
C16 C15 C8 121.4(2) . . ?
C29 C24 C25 123.5(2) . . ?
C29 C24 S2 110.86(19) . . ?
C25 C24 S2 125.53(19) . . ?
C7 C8 C9 121.5(2) . . ?
C7 C8 C15 123.8(2) . . ?
C9 C8 C15 114.6(2) . . ?
C2 C1 C6 123.2(2) . . ?
C2 C1 S1 125.8(2) . . ?
C6 C1 S1 110.92(18) . . ?
C37 C32 C33 117.2(2) . . ?
C37 C32 C31 121.1(2) . . ?
C33 C32 C31 121.6(2) . . ?
C31 C30 N2 123.6(2) . . ?
C31 C30 C29 128.2(2) . . ?
N2 C30 C29 108.2(2) . . ?
C10 C9 C14 118.1(2) . . ?
C10 C9 C8 121.2(2) . . ?
C14 C9 C8 120.6(2) . . ?
C8 C7 N1 123.6(2) . . ?
C8 C7 C6 128.6(2) . . ?
N1 C7 C6 107.6(2) . . ?
C24 C29 C28 117.3(2) . . ?
C24 C29 C30 112.7(2) . . ?
C28 C29 C30 129.9(2) . . ?
C1 C6 C5 116.6(2) . . ?
C1 C6 C7 112.4(2) . . ?
C5 C6 C7 130.9(2) . . ?
C30 C31 C32 124.2(2) . . ?
C30 C31 C39 121.5(2) . . ?
C32 C31 C39 114.2(2) . . ?
C32 C33 C34 120.8(3) . . ?
C32 C33 H33 119.6 . . ?
C34 C33 H33 119.6 . . ?
C44 C39 C40 118.4(2) . . ?
C44 C39 C31 121.0(2) . . ?
C40 C39 C31 120.6(2) . . ?
C17 C16 C15 120.5(2) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C27 C28 C29 120.6(2) . . ?
C27 C28 H28 119.7 . . ?
C29 C28 H28 119.7 . . ?
C19 C20 C15 120.6(2) . . ?
C19 C20 H20 119.7 . . ?
C15 C20 H20 119.7 . . ?
C41 C40 C39 120.8(3) . . ?
C41 C40 H40 119.6 . . ?
C39 C40 H40 119.6 . . ?
C19 C18 C17 117.6(2) . . ?
C19 C18 C21 120.7(3) . . ?
C17 C18 C21 121.7(3) . . ?
C13 C14 C9 120.6(3) . . ?
C13 C14 H14 119.7 . . ?
C9 C14 H14 119.7 . . ?
C26 C25 C24 117.3(2) . . ?
C26 C25 H25 121.4 . . ?
C24 C25 H25 121.4 . . ?
C16 C17 C18 121.5(3) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 H17 119.3 . . ?
C20 C19 C18 121.9(2) . . ?
C20 C19 H19 119.0 . . ?
C18 C19 H19 119.0 . . ?
C36 C37 C32 120.9(3) . . ?
C36 C37 H37 119.5 . . ?
C32 C37 H37 119.5 . . ?
C34 C35 C36 117.0(3) . . ?
C34 C35 C38 122.0(3) . . ?
C36 C35 C38 121.0(3) . . ?
C4 C5 C6 121.6(3) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C25 C26 C27 121.9(3) . . ?
C25 C26 H26 119.1 . . ?
C27 C26 H26 119.1 . . ?
C35 C34 C33 121.6(3) . . ?
C35 C34 H34 119.2 . . ?
C33 C34 H34 119.2 . . ?
C26 C27 C28 119.4(2) . . ?
C26 C27 C46 120.8(3) . . ?
C28 C27 C46 119.8(2) . . ?
C9 C10 C11 121.2(3) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C3 C2 C1 118.2(3) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C5 C4 C3 119.2(3) . . ?
C5 C4 C23 121.2(3) . . ?
C3 C4 C23 119.7(3) . . ?
C2 C3 C4 121.2(3) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
N1 C22 H22A 109.5 . . ?
N1 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N1 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C35 C36 C37 122.5(3) . . ?
C35 C36 H36 118.8 . . ?
C37 C36 H36 118.8 . . ?
C14 C13 C12 120.6(3) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C42 C41 C40 120.3(3) . . ?
C42 C41 H41 119.8 . . ?
C40 C41 H41 119.8 . . ?
C39 C44 C43 120.5(3) . . ?
C39 C44 H44 119.7 . . ?
C43 C44 H44 119.7 . . ?
C11 C12 C13 119.1(3) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C35 C38 H38A 109.5 . . ?
C35 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C35 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C41 C42 C43 119.8(3) . . ?
C41 C42 H42 120.1 . . ?
C43 C42 H42 120.1 . . ?
C12 C11 C10 120.3(3) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C27 C46 H46A 109.5 . . ?
C27 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
C27 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C42 C43 C44 120.2(3) . . ?
C42 C43 H43 119.9 . . ?
C44 C43 H43 119.9 . . ?
C4 C23 H23A 109.5 . . ?
C4 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C4 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N2 C45 H45A 109.5 . . ?
N2 C45 H45B 109.5 . . ?
H45A C45 H45B 109.5 . . ?
N2 C45 H45C 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.043
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
