# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_SNSB107
_database_code_depnum_ccdc_archive 'CCDC 2248017'
loop_
_audit_author_name
_audit_author_address
'Sanjib K Patra'
;IIT Kharagpur
India
;
_audit_update_record             
;
2023-03-12 deposited with the CCDC.	2023-10-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H15 N O3 S'
_chemical_formula_sum            'C18 H15 N O3 S'
_chemical_formula_weight         325.37

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                   10.5598(5)
_cell_length_b                   10.2814(4)
_cell_length_c                   15.2307(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.9780(10)
_cell_angle_gamma                90.00
_cell_volume                     1563.71(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9860
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      27.06

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9467
_exptl_absorpt_correction_T_max  0.9571
_exptl_absorpt_process_details   SADABS

_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  'Bruker-AXS Platform'
_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            59766
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_sigmaI/netI    0.0131
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.43
_diffrn_reflns_theta_max         27.09
_reflns_number_total             3445
_reflns_number_gt                2996
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_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    ORTEP
_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)+(0.0492P)²+0.5754P] 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         3445
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.1084
_refine_ls_wR_factor_gt          0.1003
_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 0.74270(4) 0.84391(4) 0.86027(3) 0.03969(13) Uani 1 1 d . . .
N1 N 0.62499(13) 0.60113(13) 0.90712(9) 0.0400(3) Uani 1 1 d . . .
O4 O 0.79931(12) 0.97759(12) 0.88213(9) 0.0540(3) Uani 1 1 d . . .
O1 O 0.35230(17) 0.92062(14) 0.87986(18) 0.1053(8) Uani 1 1 d . . .
O2 O 0.20146(12) 0.77551(12) 0.88433(9) 0.0549(3) Uani 1 1 d . . .
C16 C 0.44712(19) 0.8554(2) 0.56662(13) 0.0564(5) Uani 1 1 d . . .
H16 H 0.3869 0.8578 0.5065 0.068 Uiso 1 1 calc R . .
C15 C 0.5026(2) 0.73848(19) 0.60491(13) 0.0563(5) Uani 1 1 d . . .
H15 H 0.4803 0.6624 0.5702 0.068 Uiso 1 1 calc R . .
C14 C 0.59121(17) 0.73402(16) 0.69464(12) 0.0459(4) Uani 1 1 d . . .
H14 H 0.6292 0.6555 0.7205 0.055 Uiso 1 1 calc R . .
C13 C 0.62262(15) 0.84828(14) 0.74559(11) 0.0378(3) Uani 1 1 d . . .
C10 C 0.62548(17) 0.82993(15) 0.92508(12) 0.0433(4) Uani 1 1 d . . .
H10A H 0.6743 0.8346 0.9911 0.052 Uiso 1 1 calc R . .
H10B H 0.5631 0.9022 0.9093 0.052 Uiso 1 1 calc R . .
C1 C 0.54851(15) 0.70368(14) 0.90400(10) 0.0362(3) Uani 1 1 d . . .
C8 C 0.56804(16) 0.48041(14) 0.88992(10) 0.0378(3) Uani 1 1 d . . .
C7 C 0.65175(19) 0.37159(17) 0.89448(12) 0.0480(4) Uani 1 1 d . . .
H7 H 0.7434 0.3831 0.9074 0.058 Uiso 1 1 calc R . .
C6 C 0.5980(2) 0.24961(17) 0.87989(13) 0.0539(4) Uani 1 1 d . . .
H6 H 0.6537 0.1783 0.8835 0.065 Uiso 1 1 calc R . .
C5 C 0.4595(2) 0.23040(17) 0.85943(13) 0.0559(5) Uani 1 1 d . . .
H5 H 0.4245 0.1466 0.8496 0.067 Uiso 1 1 calc R . .
C17 C 0.48105(19) 0.96924(19) 0.61763(13) 0.0536(4) Uani 1 1 d . . .
H17 H 0.4442 1.0479 0.5914 0.064 Uiso 1 1 calc R . .
C18 C 0.56937(17) 0.96627(16) 0.70719(12) 0.0461(4) Uani 1 1 d . . .
H18 H 0.5928 1.0426 0.7414 0.055 Uiso 1 1 calc R . .
C2 C 0.40718(15) 0.69441(15) 0.88328(11) 0.0383(3) Uani 1 1 d . . .
C3 C 0.35019(16) 0.57274(15) 0.86610(12) 0.0433(4) Uani 1 1 d . . .
H3 H 0.2581 0.5639 0.8524 0.052 Uiso 1 1 calc R . .
C9 C 0.42873(16) 0.46187(15) 0.86896(10) 0.0394(3) Uani 1 1 d . . .
C4 C 0.3763(2) 0.33358(16) 0.85385(13) 0.0510(4) Uani 1 1 d . . .
H4 H 0.2848 0.3199 0.8401 0.061 Uiso 1 1 calc R . .
C11 C 0.32134(17) 0.80996(16) 0.88284(13) 0.0488(4) Uani 1 1 d . . .
C12 C 0.1090(2) 0.8790(2) 0.88447(18) 0.0697(6) Uani 1 1 d . . .
H12A H 0.1362 0.9203 0.9442 0.104 Uiso 1 1 calc R . .
H12B H 0.0207 0.8436 0.8715 0.104 Uiso 1 1 calc R . .
H12C H 0.1087 0.9417 0.8378 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 O4 1.4926(12) . ?
S1 C13 1.7944(16) . ?
S1 C10 1.8227(17) . ?
N1 C1 1.320(2) . ?
N1 C8 1.3669(19) . ?
O1 C11 1.189(2) . ?
O2 C11 1.322(2) . ?
O2 C12 1.444(2) . ?
C16 C15 1.381(3) . ?
C16 C17 1.386(3) . ?
C15 C14 1.383(3) . ?
C14 C13 1.387(2) . ?
C13 C18 1.384(2) . ?
C10 C1 1.510(2) . ?
C1 C2 1.425(2) . ?
C8 C9 1.413(2) . ?
C8 C7 1.414(2) . ?
C7 C6 1.365(2) . ?
C6 C5 1.407(3) . ?
C5 C4 1.362(3) . ?
C17 C18 1.380(2) . ?
C2 C3 1.376(2) . ?
C2 C11 1.493(2) . ?
C3 C9 1.402(2) . ?
C9 C4 1.420(2) . ?

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
O4 S1 C13 107.40(7) . . ?
O4 S1 C10 104.18(7) . . ?
C13 S1 C10 98.04(8) . . ?
C1 N1 C8 119.52(13) . . ?
C11 O2 C12 117.02(15) . . ?
C15 C16 C17 120.11(17) . . ?
C16 C15 C14 120.25(17) . . ?
C15 C14 C13 119.11(16) . . ?
C18 C13 C14 121.02(15) . . ?
C18 C13 S1 119.64(12) . . ?
C14 C13 S1 119.21(12) . . ?
C1 C10 S1 111.47(11) . . ?
N1 C1 C2 122.64(14) . . ?
N1 C1 C10 113.48(13) . . ?
C2 C1 C10 123.88(14) . . ?
N1 C8 C9 121.78(14) . . ?
N1 C8 C7 118.70(15) . . ?
C9 C8 C7 119.52(15) . . ?
C6 C7 C8 119.94(17) . . ?
C7 C6 C5 120.83(17) . . ?
C4 C5 C6 120.49(16) . . ?
C18 C17 C16 120.26(17) . . ?
C17 C18 C13 119.22(16) . . ?
C3 C2 C1 117.70(14) . . ?
C3 C2 C11 119.69(14) . . ?
C1 C2 C11 122.58(14) . . ?
C2 C3 C9 121.03(15) . . ?
C3 C9 C8 117.34(14) . . ?
C3 C9 C4 123.69(15) . . ?
C8 C9 C4 118.96(15) . . ?
C5 C4 C9 120.24(17) . . ?
O1 C11 O2 122.27(17) . . ?
O1 C11 C2 125.99(17) . . ?
O2 C11 C2 111.72(14) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.09
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.037
####################################################################### 
# 
# 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_SNSB258
_database_code_depnum_ccdc_archive 'CCDC 2248018'
loop_
_audit_author_name
_audit_author_address
'Sanjib K Patra'
;IIT Kharagpur
India
;
_audit_update_record             
;
2023-03-12 deposited with the CCDC.	2023-10-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17.60 H12 Br0.80 N1.60 O4'
_chemical_formula_sum            'C17.60 H12 Br0.80 N1.60 O4'
_chemical_formula_weight         373.82

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'
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'
Br Br -0.2901 2.4595 '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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   8.0568(9)
_cell_length_b                   10.5478(11)
_cell_length_c                   23.068(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1960.4(4)
_cell_formula_units_Z            5
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5772
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      23.14

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             944
_exptl_absorpt_coefficient_mu    2.135
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.6747
_exptl_absorpt_correction_T_max  0.7401
_exptl_absorpt_process_details   SADABS

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            41669
_diffrn_reflns_av_R_equivalents  0.0721
_diffrn_reflns_av_sigmaI/netI    0.0318
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.12
_diffrn_reflns_theta_max         26.84
_reflns_number_total             4204
_reflns_number_gt                3235
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_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    ORTEP
_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)+(0.0634P)²+2.7386P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.351(19)
_refine_ls_number_reflns         4204
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0824
_refine_ls_R_factor_gt           0.0604
_refine_ls_wR_factor_ref         0.1592
_refine_ls_wR_factor_gt          0.1451
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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
Br1 Br 0.00088(12) 0.02325(7) 0.24527(3) 0.0976(3) Uani 1 1 d . . .
O3 O 0.5174(5) 0.6343(4) 0.60757(16) 0.0657(10) Uani 1 1 d . . .
C10 C -0.0206(6) 0.3002(4) 0.4042(2) 0.0448(10) Uani 1 1 d . . .
N1 N -0.0360(5) 0.3802(4) 0.44942(17) 0.0458(9) Uani 1 1 d . . .
C12 C 0.2665(6) 0.3774(4) 0.4596(2) 0.0415(10) Uani 1 1 d . . .
C3 C 0.2251(5) 0.5573(4) 0.5493(2) 0.0408(10) Uani 1 1 d . . .
O2 O 0.6825(4) 0.5317(4) 0.54531(15) 0.0571(9) Uani 1 1 d . . .
O1 O 0.5538(4) 0.3799(3) 0.47166(15) 0.0490(8) Uani 1 1 d . . .
H1 H 0.6288 0.4124 0.4906 0.059 Uiso 1 1 calc R . .
C13 C 0.1036(6) 0.4180(4) 0.4766(2) 0.0418(10) Uani 1 1 d . . .
C2 C 0.3910(5) 0.5160(4) 0.5331(2) 0.0398(9) Uani 1 1 d . . .
C5 C -0.1651(7) 0.2613(6) 0.3748(3) 0.0554(13) Uani 1 1 d . . .
H5 H -0.2681 0.2896 0.3876 0.067 Uiso 1 1 calc R . .
C7 C -0.0032(9) 0.1369(5) 0.3093(2) 0.0633(14) Uani 1 1 d . . .
O5 O 0.0193(6) 0.9212(4) 0.75897(16) 0.0780(11) Uani 1 1 d . . .
C1 C 0.4072(5) 0.4261(4) 0.48962(19) 0.0399(10) Uani 1 1 d . . .
C11 C 0.1360(6) 0.2534(5) 0.3839(2) 0.0501(12) Uani 1 1 d . . .
C4 C 0.0891(6) 0.5064(4) 0.5224(2) 0.0455(11) Uani 1 1 d . . .
H4 H -0.0161 0.5307 0.5347 0.055 Uiso 1 1 calc R . .
C14 C 0.5432(6) 0.5610(5) 0.5614(2) 0.0472(11) Uani 1 1 d . . .
C22 C 0.2177(7) 0.7851(5) 0.5781(2) 0.0507(12) Uani 1 1 d . . .
H22 H 0.2626 0.8053 0.5422 0.061 Uiso 1 1 calc R . .
C19 C 0.0872(7) 0.7242(5) 0.6856(2) 0.0505(12) Uani 1 1 d . . .
H19 H 0.0451 0.7042 0.7220 0.061 Uiso 1 1 calc R . .
C6 C -0.1568(8) 0.1830(6) 0.3281(3) 0.0594(15) Uani 1 1 d . . .
H6 H -0.2533 0.1602 0.3086 0.071 Uiso 1 1 calc R . .
C17 C 0.1928(5) 0.6601(4) 0.59241(19) 0.0383(10) Uani 1 1 d . . .
N2 N 0.0594(6) 0.9504(4) 0.7088(2) 0.0582(11) Uani 1 1 d . . .
C21 C 0.1773(7) 0.8818(5) 0.6163(2) 0.0490(11) Uani 1 1 d . . .
H21 H 0.1950 0.9664 0.6066 0.059 Uiso 1 1 calc R . .
C18 C 0.1285(6) 0.6302(5) 0.6467(2) 0.0492(11) Uani 1 1 d . . .
H18 H 0.1132 0.5457 0.6569 0.059 Uiso 1 1 calc R . .
C20 C 0.1098(6) 0.8486(5) 0.6693(2) 0.0445(10) Uani 1 1 d . . .
C8 C 0.1413(8) 0.1695(6) 0.3358(3) 0.0610(15) Uani 1 1 d . . .
H8 H 0.2419 0.1374 0.3226 0.073 Uiso 1 1 calc R . .
C9 C 0.2795(7) 0.2934(5) 0.4130(2) 0.0520(12) Uani 1 1 d . . .
H9 H 0.3831 0.2641 0.4014 0.062 Uiso 1 1 calc R . .
C16 C 0.6998(11) 0.8138(8) 0.6078(4) 0.105(3) Uani 1 1 d . . .
H16A H 0.7496 0.7985 0.5707 0.158 Uiso 1 1 calc R . .
H16B H 0.7756 0.8609 0.6317 0.158 Uiso 1 1 calc R . .
H16C H 0.5994 0.8615 0.6029 0.158 Uiso 1 1 calc R . .
C15 C 0.6612(8) 0.6909(6) 0.6361(3) 0.0747(19) Uani 1 1 d . . .
H15A H 0.7558 0.6344 0.6331 0.090 Uiso 1 1 calc R . .
H15B H 0.6374 0.7043 0.6769 0.090 Uiso 1 1 calc R . .
O4 O 0.0568(7) 1.0587(4) 0.6910(2) 0.0941(17) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C7 1.902(5) . ?
O3 C14 1.332(6) . ?
O3 C15 1.460(6) . ?
C10 N1 1.347(6) . ?
C10 C5 1.409(7) . ?
C10 C11 1.433(7) . ?
N1 C13 1.349(6) . ?
C12 C9 1.396(7) . ?
C12 C1 1.424(7) . ?
C12 C13 1.435(6) . ?
C3 C4 1.368(7) . ?
C3 C2 1.455(6) . ?
C3 C17 1.495(6) . ?
O2 C14 1.222(6) . ?
O1 C1 1.343(5) . ?
C13 C4 1.414(6) . ?
C2 C1 1.387(6) . ?
C2 C14 1.467(6) . ?
C5 C6 1.359(8) . ?
C7 C8 1.359(8) . ?
C7 C6 1.398(9) . ?
O5 N2 1.241(6) . ?
C11 C9 1.402(7) . ?
C11 C8 1.421(7) . ?
C22 C17 1.374(7) . ?
C22 C21 1.386(7) . ?
C19 C20 1.376(7) . ?
C19 C18 1.378(7) . ?
C17 C18 1.392(6) . ?
N2 O4 1.215(6) . ?
N2 C20 1.466(6) . ?
C21 C20 1.383(7) . ?
C16 C15 1.485(10) . ?

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
C14 O3 C15 118.3(4) . . ?
N1 C10 C5 118.6(5) . . ?
N1 C10 C11 123.4(4) . . ?
C5 C10 C11 118.0(4) . . ?
C10 N1 C13 117.9(4) . . ?
C9 C12 C1 122.9(4) . . ?
C9 C12 C13 118.0(4) . . ?
C1 C12 C13 119.2(4) . . ?
C4 C3 C2 120.2(4) . . ?
C4 C3 C17 116.5(4) . . ?
C2 C3 C17 123.2(4) . . ?
N1 C13 C4 118.3(4) . . ?
N1 C13 C12 123.2(4) . . ?
C4 C13 C12 118.5(4) . . ?
C1 C2 C3 118.4(4) . . ?
C1 C2 C14 117.7(4) . . ?
C3 C2 C14 123.9(4) . . ?
C6 C5 C10 121.2(5) . . ?
C8 C7 C6 122.0(5) . . ?
C8 C7 Br1 119.6(5) . . ?
C6 C7 Br1 118.4(5) . . ?
O1 C1 C2 123.6(4) . . ?
O1 C1 C12 114.8(4) . . ?
C2 C1 C12 121.6(4) . . ?
C9 C11 C8 122.5(5) . . ?
C9 C11 C10 117.7(5) . . ?
C8 C11 C10 119.7(5) . . ?
C3 C4 C13 122.1(4) . . ?
O2 C14 O3 122.2(4) . . ?
O2 C14 C2 123.4(5) . . ?
O3 C14 C2 114.4(4) . . ?
C17 C22 C21 121.3(5) . . ?
C20 C19 C18 118.4(4) . . ?
C5 C6 C7 120.1(5) . . ?
C22 C17 C18 119.2(5) . . ?
C22 C17 C3 120.8(4) . . ?
C18 C17 C3 119.9(4) . . ?
O4 N2 O5 122.9(5) . . ?
O4 N2 C20 119.0(4) . . ?
O5 N2 C20 118.1(4) . . ?
C20 C21 C22 117.8(5) . . ?
C19 C18 C17 120.8(5) . . ?
C19 C20 C21 122.4(5) . . ?
C19 C20 N2 119.4(4) . . ?
C21 C20 N2 118.2(4) . . ?
C7 C8 C11 118.9(5) . . ?
C12 C9 C11 119.8(5) . . ?
O3 C15 C16 108.9(6) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.84
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.107
_refine_diff_density_min         -0.994
_refine_diff_density_rms         0.065
####################################################################### 
# 
# 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_SNSB253
_database_code_depnum_ccdc_archive 'CCDC 2248019'
loop_
_audit_author_name
_audit_author_address
'Sanjib K Patra'
;IIT Kharagpur
India
;
_audit_update_record             
;
2023-03-12 deposited with the CCDC.	2023-10-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H13 N O3'
_chemical_formula_sum            'C16 H13 N O3'
_chemical_formula_weight         267.27

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'

_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                   7.110(2)
_cell_length_b                   7.857(3)
_cell_length_c                   11.773(4)
_cell_angle_alpha                82.026(13)
_cell_angle_beta                 79.905(13)
_cell_angle_gamma                85.894(13)
_cell_volume                     640.5(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1653
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      25.62

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             280
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9716
_exptl_absorpt_correction_T_max  0.9809
_exptl_absorpt_process_details   SADABS

_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  Bruker-AXS
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12012
_diffrn_reflns_av_R_equivalents  0.0613
_diffrn_reflns_av_sigmaI/netI    0.0824
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.62
_diffrn_reflns_theta_max         33.09
_reflns_number_total             3997
_reflns_number_gt                1643
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_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    ORTEP
_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)+(0.0773P)²+0.0472P] 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         3997
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1764
_refine_ls_R_factor_gt           0.0652
_refine_ls_wR_factor_ref         0.2081
_refine_ls_wR_factor_gt          0.1617
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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
O1 O 0.26378(18) 0.1636(2) 0.66901(12) 0.0625(4) Uani 1 1 d . . .
H1 H 0.2712 0.0998 0.7295 0.075 Uiso 1 1 calc R . .
N1 N 0.6481(2) 0.3844(2) 0.30963(13) 0.0495(4) Uani 1 1 d . . .
C1 C 0.4381(3) 0.1752(2) 0.60294(15) 0.0454(5) Uani 1 1 d . . .
C11 C 0.3031(3) 0.4506(2) 0.34106(16) 0.0463(5) Uani 1 1 d . . .
C14 C 0.5901(3) 0.0011(3) 0.75457(17) 0.0519(5) Uani 1 1 d . . .
C9 C 0.2851(3) 0.3544(2) 0.45062(16) 0.0494(5) Uani 1 1 d . . .
H9 H 0.1654 0.3434 0.4971 0.059 Uiso 1 1 calc R . .
C13 C 0.6274(3) 0.2914(2) 0.41542(16) 0.0441(5) Uani 1 1 d . . .
C2 C 0.6026(3) 0.1001(2) 0.63870(16) 0.0462(5) Uani 1 1 d . . .
C12 C 0.4464(2) 0.2748(2) 0.49028(15) 0.0432(5) Uani 1 1 d . . .
C5 C 0.5102(3) 0.5634(3) 0.16179(17) 0.0579(6) Uani 1 1 d . . .
H5 H 0.6306 0.5727 0.1160 0.070 Uiso 1 1 calc R . .
O3 O 0.7593(2) -0.06085(18) 0.77946(11) 0.0591(4) Uani 1 1 d . . .
C3 C 0.7815(3) 0.1192(2) 0.56178(16) 0.0508(5) Uani 1 1 d . . .
H3 H 0.8923 0.0688 0.5864 0.061 Uiso 1 1 calc R . .
C10 C 0.4901(3) 0.4629(2) 0.27317(16) 0.0475(5) Uani 1 1 d . . .
C7 C 0.1725(3) 0.6336(3) 0.18912(19) 0.0642(6) Uani 1 1 d . . .
H7 H 0.0684 0.6919 0.1607 0.077 Uiso 1 1 calc R . .
C4 C 0.7937(3) 0.2081(2) 0.45469(17) 0.0505(5) Uani 1 1 d . . .
H4 H 0.9116 0.2154 0.4058 0.061 Uiso 1 1 calc R . .
C6 C 0.3561(3) 0.6458(3) 0.12151(18) 0.0636(6) Uani 1 1 d . . .
H6 H 0.3720 0.7109 0.0485 0.076 Uiso 1 1 calc R . .
O2 O 0.4406(2) -0.0220(2) 0.82303(12) 0.0668(5) Uani 1 1 d . . .
C8 C 0.1458(3) 0.5380(3) 0.29501(18) 0.0578(6) Uani 1 1 d . . .
H8 H 0.0232 0.5295 0.3380 0.069 Uiso 1 1 calc R . .
C16 C 0.9650(3) -0.2037(4) 0.9044(2) 0.0918(9) Uani 1 1 d . . .
H16A H 1.0273 -0.2606 0.8398 0.138 Uiso 1 1 calc R . .
H16B H 0.9711 -0.2782 0.9756 0.138 Uiso 1 1 calc R . .
H16C H 1.0279 -0.0998 0.9051 0.138 Uiso 1 1 calc R . .
C15 C 0.7617(3) -0.1609(3) 0.89280(17) 0.0668(6) Uani 1 1 d . . .
H15A H 0.6938 -0.2654 0.8989 0.080 Uiso 1 1 calc R . .
H15B H 0.7001 -0.0948 0.9539 0.080 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
O1 C1 1.345(2) . ?
N1 C13 1.344(2) . ?
N1 C10 1.350(2) . ?
C1 C2 1.377(3) . ?
C1 C12 1.437(3) . ?
C11 C9 1.392(3) . ?
C11 C8 1.420(3) . ?
C11 C10 1.429(3) . ?
C14 O2 1.225(2) . ?
C14 O3 1.331(2) . ?
C14 C2 1.465(3) . ?
C9 C12 1.389(3) . ?
C13 C4 1.427(3) . ?
C13 C12 1.430(2) . ?
C2 C3 1.431(3) . ?
C5 C6 1.356(3) . ?
C5 C10 1.424(3) . ?
O3 C15 1.454(2) . ?
C3 C4 1.346(3) . ?
C7 C8 1.354(3) . ?
C7 C6 1.407(3) . ?
C16 C15 1.485(3) . ?

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
C13 N1 C10 117.99(16) . . ?
O1 C1 C2 123.59(17) . . ?
O1 C1 C12 116.02(17) . . ?
C2 C1 C12 120.38(17) . . ?
C9 C11 C8 123.19(18) . . ?
C9 C11 C10 117.82(18) . . ?
C8 C11 C10 118.99(18) . . ?
O2 C14 O3 122.65(19) . . ?
O2 C14 C2 124.2(2) . . ?
O3 C14 C2 113.16(17) . . ?
C12 C9 C11 119.75(17) . . ?
N1 C13 C4 118.35(16) . . ?
N1 C13 C12 122.63(18) . . ?
C4 C13 C12 119.02(17) . . ?
C1 C2 C3 119.42(18) . . ?
C1 C2 C14 119.17(17) . . ?
C3 C2 C14 121.41(19) . . ?
C9 C12 C13 118.56(18) . . ?
C9 C12 C1 122.59(17) . . ?
C13 C12 C1 118.84(18) . . ?
C6 C5 C10 120.89(19) . . ?
C14 O3 C15 117.28(16) . . ?
C4 C3 C2 121.72(19) . . ?
N1 C10 C5 118.61(17) . . ?
N1 C10 C11 123.23(18) . . ?
C5 C10 C11 118.17(19) . . ?
C8 C7 C6 120.7(2) . . ?
C3 C4 C13 120.58(17) . . ?
C5 C6 C7 120.6(2) . . ?
C7 C8 C11 120.64(19) . . ?
O3 C15 C16 107.53(18) . . ?

_diffrn_measured_fraction_theta_max 0.823
_diffrn_reflns_theta_full        33.09
_diffrn_measured_fraction_theta_full 0.823
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.043
####################################################################### 
# 
# 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_SNSB229
_database_code_depnum_ccdc_archive 'CCDC 2248021'
loop_
_audit_author_name
_audit_author_address
'Sanjib K Patra'
;IIT Kharagpur
India
;
_audit_update_record             
;
2023-03-12 deposited with the CCDC.	2023-10-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C84 H56 Br4 N4 O12'
_chemical_formula_sum            'C84 H56 Br4 N4 O12'
_chemical_formula_weight         1632.97

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'
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'
Br Br -0.2901 2.4595 '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'

_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                   5.315(2)
_cell_length_b                   14.209(3)
_cell_length_c                   22.732(5)
_cell_angle_alpha                90.03(3)
_cell_angle_beta                 91.78(3)
_cell_angle_gamma                90.00(3)
_cell_volume                     1716.0(8)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_absorpt_coefficient_mu    2.417
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.5309
_exptl_absorpt_correction_T_max  0.6436
_exptl_absorpt_process_details   SADABS

_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  'Bruker-AXS Platform'
_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            28932
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_av_sigmaI/netI    0.0296
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.29
_diffrn_reflns_theta_max         27.93
_reflns_number_total             3785
_reflns_number_gt                2913
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_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    ORTEP
_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)+(0.0268P)²+1.5900P] 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         3785
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.0816
_refine_ls_wR_factor_gt          0.0752
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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
Br1 Br -0.45644(5) 0.87310(2) 0.680997(12) 0.04928(11) Uani 1 1 d . . .
O1 O 0.5432(4) 0.94041(14) 0.42264(9) 0.0535(5) Uani 1 1 d . . .
H1 H 0.6177 0.9569 0.3933 0.064 Uiso 1 1 calc R . .
O3 O 1.1452(3) 0.80643(14) 0.34228(9) 0.0498(5) Uani 1 1 d . . .
N1 N 0.3891(4) 0.67474(16) 0.54714(9) 0.0398(5) Uani 1 1 d . . .
O2 O 0.8704(4) 0.92413(16) 0.33796(10) 0.0651(6) Uani 1 1 d . . .
C3 C 0.8219(4) 0.70036(18) 0.42088(11) 0.0348(6) Uani 1 1 d . . .
C2 C 0.7828(5) 0.79801(19) 0.40465(11) 0.0371(6) Uani 1 1 d . . .
C13 C 0.1323(5) 0.81738(18) 0.55975(10) 0.0359(6) Uani 1 1 d . . .
C12 C 0.2035(5) 0.72337(19) 0.57537(11) 0.0373(6) Uani 1 1 d . . .
C16 C 0.9777(4) 0.63492(18) 0.38330(11) 0.0362(6) Uani 1 1 d . . .
C8 C -0.0690(5) 0.86232(19) 0.59200(11) 0.0394(6) Uani 1 1 d . . .
H8 H -0.1180 0.9233 0.5822 0.047 Uiso 1 1 calc R . .
C11 C 0.5144(5) 0.71722(19) 0.50234(11) 0.0357(6) Uani 1 1 d . . .
C10 C 0.4580(5) 0.81102(18) 0.48402(10) 0.0360(6) Uani 1 1 d . . .
C4 C 0.6984(5) 0.66476(19) 0.46923(11) 0.0381(6) Uani 1 1 d . . .
H4 H 0.7357 0.6036 0.4811 0.046 Uiso 1 1 calc R . .
C7 C -0.1879(5) 0.8160(2) 0.63674(11) 0.0394(6) Uani 1 1 d . . .
C9 C 0.2658(5) 0.85962(19) 0.51330(11) 0.0389(6) Uani 1 1 d . . .
H9 H 0.2257 0.9208 0.5019 0.047 Uiso 1 1 calc R . .
C1 C 0.6004(5) 0.85025(18) 0.43525(11) 0.0384(6) Uani 1 1 d . . .
C17 C 0.9286(5) 0.6238(2) 0.32382(11) 0.0443(6) Uani 1 1 d . . .
H17 H 0.7965 0.6573 0.3061 0.053 Uiso 1 1 calc R . .
C14 C 0.9331(5) 0.8481(2) 0.35877(12) 0.0420(6) Uani 1 1 d . . .
C21 C 1.1674(5) 0.5814(2) 0.40741(13) 0.0435(6) Uani 1 1 d . . .
H21 H 1.2019 0.5844 0.4477 0.052 Uiso 1 1 calc R . .
C6 C -0.1206(5) 0.7234(2) 0.65265(12) 0.0478(7) Uani 1 1 d . . .
H6 H -0.2020 0.6927 0.6828 0.057 Uiso 1 1 calc R . .
C5 C 0.0690(5) 0.6784(2) 0.62269(12) 0.0477(7) Uani 1 1 d . . .
H5 H 0.1119 0.6171 0.6333 0.057 Uiso 1 1 calc R . .
C19 C 1.2676(6) 0.5138(2) 0.31290(15) 0.0539(8) Uani 1 1 d . . .
H19 H 1.3674 0.4760 0.2897 0.065 Uiso 1 1 calc R . .
C18 C 1.0723(6) 0.5634(2) 0.28899(13) 0.0491(7) Uani 1 1 d . . .
H18 H 1.0325 0.5574 0.2490 0.059 Uiso 1 1 calc R . .
C20 C 1.3129(5) 0.5213(2) 0.37218(15) 0.0535(8) Uani 1 1 d . . .
H20 H 1.4421 0.4861 0.3898 0.064 Uiso 1 1 calc R . .
C15 C 1.2839(6) 0.8468(3) 0.29267(14) 0.0609(9) Uani 1 1 d . . .
H15A H 1.1759 0.8482 0.2580 0.091 Uiso 1 1 calc R . .
H15B H 1.4289 0.8087 0.2854 0.091 Uiso 1 1 calc R . .
H15C H 1.3367 0.9097 0.3024 0.091 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
Br1 C7 1.948(3) . ?
O1 C1 1.346(3) . ?
O1 H1 0.8200 . ?
O3 C14 1.337(3) . ?
O3 C15 1.482(3) . ?
N1 C11 1.374(3) . ?
N1 C12 1.379(3) . ?
O2 C14 1.222(3) . ?
C3 C4 1.393(4) . ?
C3 C2 1.449(4) . ?
C3 C16 1.524(3) . ?
C2 C1 1.420(4) . ?
C2 C14 1.511(4) . ?
C13 C9 1.423(4) . ?
C13 C12 1.430(4) . ?
C13 C8 1.462(4) . ?
C12 C5 1.458(4) . ?
C16 C21 1.365(4) . ?
C16 C17 1.378(4) . ?
C8 C7 1.381(4) . ?
C8 H8 0.9300 . ?
C11 C10 1.426(4) . ?
C11 C4 1.457(4) . ?
C10 C9 1.416(4) . ?
C10 C1 1.472(4) . ?
C4 H4 0.9300 . ?
C7 C6 1.408(4) . ?
C9 H9 0.9300 . ?
C17 C18 1.409(4) . ?
C17 H17 0.9300 . ?
C21 C20 1.416(4) . ?
C21 H21 0.9300 . ?
C6 C5 1.390(4) . ?
C6 H6 0.9300 . ?
C5 H5 0.9300 . ?
C19 C18 1.354(4) . ?
C19 C20 1.366(4) . ?
C19 H19 0.9300 . ?
C18 H18 0.9300 . ?
C20 H20 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
C14 O3 C15 119.0(2) . . ?
C11 N1 C12 119.7(2) . . ?
C4 C3 C2 118.8(2) . . ?
C4 C3 C16 119.9(2) . . ?
C2 C3 C16 121.2(2) . . ?
C1 C2 C3 118.1(2) . . ?
C1 C2 C14 118.4(2) . . ?
C3 C2 C14 123.5(2) . . ?
C9 C13 C12 116.4(2) . . ?
C9 C13 C8 125.2(2) . . ?
C12 C13 C8 118.4(2) . . ?
N1 C12 C13 122.7(2) . . ?
N1 C12 C5 119.8(2) . . ?
C13 C12 C5 117.5(2) . . ?
C21 C16 C17 116.4(3) . . ?
C21 C16 C3 121.5(2) . . ?
C17 C16 C3 122.0(2) . . ?
C7 C8 C13 121.3(2) . . ?
C7 C8 H8 119.4 . . ?
C13 C8 H8 119.4 . . ?
N1 C11 C10 121.7(2) . . ?
N1 C11 C4 120.4(2) . . ?
C10 C11 C4 117.7(2) . . ?
C9 C10 C11 117.8(2) . . ?
C9 C10 C1 124.4(2) . . ?
C11 C10 C1 117.8(2) . . ?
C3 C4 C11 124.2(2) . . ?
C3 C4 H4 117.9 . . ?
C11 C4 H4 117.9 . . ?
C8 C7 C6 121.1(2) . . ?
C8 C7 Br1 122.7(2) . . ?
C6 C7 Br1 116.2(2) . . ?
C10 C9 C13 121.8(2) . . ?
C10 C9 H9 119.1 . . ?
C13 C9 H9 119.1 . . ?
O1 C1 C2 123.1(2) . . ?
O1 C1 C10 113.8(2) . . ?
C2 C1 C10 123.1(2) . . ?
C16 C17 C18 122.1(3) . . ?
C16 C17 H17 118.9 . . ?
C18 C17 H17 118.9 . . ?
O2 C14 O3 120.3(3) . . ?
O2 C14 C2 122.7(3) . . ?
O3 C14 C2 116.9(2) . . ?
C16 C21 C20 121.2(3) . . ?
C16 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
C5 C6 C7 119.1(3) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C6 C5 C12 122.6(3) . . ?
C6 C5 H5 118.7 . . ?
C12 C5 H5 118.7 . . ?
C18 C19 C20 117.7(3) . . ?
C18 C19 H19 121.1 . . ?
C20 C19 H19 121.1 . . ?
C19 C18 C17 120.9(3) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C19 C20 C21 121.5(3) . . ?
C19 C20 H20 119.3 . . ?
C21 C20 H20 119.3 . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.926
_diffrn_reflns_theta_full        27.93
_diffrn_measured_fraction_theta_full 0.926
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.053
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_SNSB133
_database_code_depnum_ccdc_archive 'CCDC 2248020'
loop_
_audit_author_name
_audit_author_address
'Sanjib K Patra'
;IIT Kharagpur
India
;
_audit_update_record             
;
2023-03-12 deposited with the CCDC.	2023-10-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H15 N O3'
_chemical_formula_sum            'C21 H15 N O3'
_chemical_formula_weight         329.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   6.384(4)
_cell_length_b                   11.473(5)
_cell_length_c                   11.661(6)
_cell_angle_alpha                75.635(12)
_cell_angle_beta                 88.166(16)
_cell_angle_gamma                74.104(13)
_cell_volume                     795.2(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9914
_cell_measurement_theta_min      3.32
_cell_measurement_theta_max      27.07

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             344
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9728
_exptl_absorpt_correction_T_max  0.9817
_exptl_absorpt_process_details   SADABS

_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  'Bruker-AXS Platform'
_diffrn_measurement_method       "'ω scans"
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            46112
_diffrn_reflns_av_R_equivalents  0.0633
_diffrn_reflns_av_sigmaI/netI    0.0275
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.32
_diffrn_reflns_theta_max         27.89
_reflns_number_total             3797
_reflns_number_gt                2883
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_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    ORTEP
_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)+(0.0752P)²+0.1824P] 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         3797
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0509
_refine_ls_wR_factor_ref         0.1628
_refine_ls_wR_factor_gt          0.1452
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_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
O1 O 0.6696(2) 0.96821(10) 0.60946(11) 0.0569(3) Uani 1 1 d . . .
H1 H 0.7770 0.9680 0.5689 0.068 Uiso 1 1 calc R . .
O2 O 1.0236(2) 0.86816(12) 0.52039(13) 0.0777(4) Uani 1 1 d . . .
N1 N 0.3511(2) 0.70413(11) 0.90092(11) 0.0469(3) Uani 1 1 d . . .
C4 C -0.2029(3) 0.99700(18) 0.89564(16) 0.0615(5) Uani 1 1 d . . .
H4 H -0.3287 1.0611 0.8964 0.074 Uiso 1 1 calc R . .
C3 C -0.1813(3) 0.87736(18) 0.97053(16) 0.0604(4) Uani 1 1 d . . .
H3 H -0.2942 0.8632 1.0196 0.072 Uiso 1 1 calc R . .
C2 C 0.0009(3) 0.78218(16) 0.97271(15) 0.0541(4) Uani 1 1 d . . .
H2 H 0.0125 0.7040 1.0236 0.065 Uiso 1 1 calc R . .
C1 C 0.1744(2) 0.80160(14) 0.89733(13) 0.0442(3) Uani 1 1 d . . .
C7 C 0.5117(2) 0.72225(13) 0.82704(13) 0.0428(3) Uani 1 1 d . . .
C8 C 0.6926(3) 0.61779(13) 0.82462(14) 0.0469(4) Uani 1 1 d . . .
H8 H 0.6974 0.5405 0.8755 0.056 Uiso 1 1 calc R . .
C9 C 0.8588(2) 0.62782(13) 0.74996(13) 0.0429(3) Uani 1 1 d . . .
C16 C 1.0300(2) 0.51003(13) 0.74607(13) 0.0432(3) Uani 1 1 d . . .
C21 C 1.2163(3) 0.46672(15) 0.81870(15) 0.0527(4) Uani 1 1 d . . .
H21 H 1.2376 0.5113 0.8719 0.063 Uiso 1 1 calc R . .
C20 C 1.3715(3) 0.35729(16) 0.81279(16) 0.0596(4) Uani 1 1 d . . .
H20 H 1.4970 0.3293 0.8614 0.072 Uiso 1 1 calc R . .
O3 O 1.2054(2) 0.67395(12) 0.60034(12) 0.0699(4) Uani 1 1 d . . .
C19 C 1.3411(3) 0.29000(16) 0.73555(16) 0.0597(4) Uani 1 1 d . . .
H19 H 1.4462 0.2170 0.7314 0.072 Uiso 1 1 calc R . .
C6 C 0.1514(2) 0.92302(14) 0.82040(13) 0.0457(3) Uani 1 1 d . . .
C13 C 0.3227(3) 0.94029(14) 0.74686(14) 0.0464(3) Uani 1 1 d . . .
H13 H 0.3145 1.0183 0.6963 0.056 Uiso 1 1 calc R . .
C12 C 0.5051(2) 0.84075(13) 0.74941(13) 0.0418(3) Uani 1 1 d . . .
C11 C 0.6858(2) 0.85244(13) 0.67477(13) 0.0431(3) Uani 1 1 d . . .
C10 C 0.8594(2) 0.74878(13) 0.67372(13) 0.0423(3) Uani 1 1 d . . .
C14 C 1.0342(3) 0.76993(14) 0.59219(13) 0.0465(3) Uani 1 1 d . . .
C15 C 1.3764(3) 0.6891(2) 0.51929(19) 0.0720(5) Uani 1 1 d . . .
H15A H 1.3230 0.7021 0.4398 0.108 Uiso 1 1 calc R . .
H15B H 1.4972 0.6153 0.5384 0.108 Uiso 1 1 calc R . .
H15C H 1.4232 0.7601 0.5257 0.108 Uiso 1 1 calc R . .
C18 C 1.1562(3) 0.33065(18) 0.66503(18) 0.0685(5) Uani 1 1 d . . .
H18 H 1.1342 0.2845 0.6135 0.082 Uiso 1 1 calc R . .
C17 C 1.0011(3) 0.44017(17) 0.66975(16) 0.0613(5) Uani 1 1 d . . .
H17 H 0.8758 0.4672 0.6210 0.074 Uiso 1 1 calc R . .
C5 C -0.0421(3) 1.01976(16) 0.82230(16) 0.0566(4) Uani 1 1 d . . .
H5 H -0.0584 1.0992 0.7729 0.068 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
O1 C11 1.3352(18) . ?
O2 C14 1.212(2) . ?
N1 C7 1.345(2) . ?
N1 C1 1.347(2) . ?
C4 C5 1.354(3) . ?
C4 C3 1.405(3) . ?
C3 C2 1.356(2) . ?
C2 C1 1.423(2) . ?
C1 C6 1.429(2) . ?
C7 C8 1.424(2) . ?
C7 C12 1.425(2) . ?
C8 C9 1.362(2) . ?
C9 C10 1.452(2) . ?
C9 C16 1.497(2) . ?
C16 C21 1.382(2) . ?
C16 C17 1.383(2) . ?
C21 C20 1.385(2) . ?
C20 C19 1.372(3) . ?
O3 C14 1.309(2) . ?
O3 C15 1.439(2) . ?
C19 C18 1.363(3) . ?
C6 C13 1.394(2) . ?
C6 C5 1.421(2) . ?
C13 C12 1.385(2) . ?
C12 C11 1.439(2) . ?
C11 C10 1.388(2) . ?
C10 C14 1.474(2) . ?
C18 C17 1.383(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 C1 117.98(13) . . ?
C5 C4 C3 120.53(16) . . ?
C2 C3 C4 121.32(16) . . ?
C3 C2 C1 120.19(16) . . ?
N1 C1 C2 118.31(14) . . ?
N1 C1 C6 123.23(14) . . ?
C2 C1 C6 118.45(14) . . ?
N1 C7 C8 118.40(13) . . ?
N1 C7 C12 122.63(14) . . ?
C8 C7 C12 118.95(13) . . ?
C9 C8 C7 121.92(13) . . ?
C8 C9 C10 119.91(13) . . ?
C8 C9 C16 117.59(13) . . ?
C10 C9 C16 122.43(13) . . ?
C21 C16 C17 118.37(15) . . ?
C21 C16 C9 121.91(14) . . ?
C17 C16 C9 119.71(14) . . ?
C16 C21 C20 120.39(16) . . ?
C19 C20 C21 120.39(16) . . ?
C14 O3 C15 117.43(14) . . ?
C18 C19 C20 119.72(16) . . ?
C13 C6 C5 123.21(15) . . ?
C13 C6 C1 117.69(14) . . ?
C5 C6 C1 119.10(15) . . ?
C12 C13 C6 119.67(14) . . ?
C13 C12 C7 118.75(14) . . ?
C13 C12 C11 122.23(13) . . ?
C7 C12 C11 119.01(13) . . ?
O1 C11 C10 124.67(14) . . ?
O1 C11 C12 114.62(13) . . ?
C10 C11 C12 120.71(13) . . ?
C11 C10 C9 119.38(13) . . ?
C11 C10 C14 116.57(13) . . ?
C9 C10 C14 124.04(13) . . ?
O2 C14 O3 120.74(15) . . ?
O2 C14 C10 123.64(15) . . ?
O3 C14 C10 115.62(13) . . ?
C19 C18 C17 120.29(17) . . ?
C18 C17 C16 120.83(17) . . ?
C4 C5 C6 120.40(16) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.89
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.038
