# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_1090
_database_code_depnum_ccdc_archive 'CCDC 2096228'
loop_
_audit_author_name
_audit_author_address
'V RAMKUMAR '
;Technical officer  Chemistry department IIT Madras
India
;
_audit_update_record             
;
2021-07-13 deposited with the CCDC.	2022-01-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H20 N2 O3'
_chemical_formula_weight         396.43

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   9.5635(6)
_cell_length_b                   6.7073(3)
_cell_length_c                   15.8118(8)
_cell_angle_alpha                90
_cell_angle_beta                 90.829(3)
_cell_angle_gamma                90
_cell_volume                     1014.15(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2475
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      22.49

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_F_000             416
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7813
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.130
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3558
_reflns_number_gt                2715
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.826
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.998

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0388P)²+0.0483P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.037(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 965 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.3(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3558
_refine_ls_number_parameters     277
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.0909
_refine_ls_wR_factor_gt          0.0798
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6521(3) 0.5406(5) 0.3619(2) 0.0552(9) Uani 1 1 d . . . . .
H1A H 0.6850 0.6772 0.3654 0.066 Uiso 1 1 calc R U . . .
H1B H 0.5985 0.5261 0.3097 0.066 Uiso 1 1 calc R U . . .
C2 C 0.6299(4) 0.4755(5) 0.5093(2) 0.0529(8) Uani 1 1 d . . . . .
C3 C 0.5441(4) 0.4856(5) 0.5796(2) 0.0690(11) Uani 1 1 d . . . . .
H3 H 0.4488 0.5094 0.5729 0.083 Uiso 1 1 calc R U . . .
C4 C 0.6014(5) 0.4601(6) 0.6586(2) 0.0766(12) Uani 1 1 d . . . . .
H4 H 0.5436 0.4638 0.7054 0.092 Uiso 1 1 calc R U . . .
C5 C 0.7418(4) 0.4291(6) 0.6704(2) 0.0706(10) Uani 1 1 d . . . . .
H5 H 0.7791 0.4143 0.7247 0.085 Uiso 1 1 calc R U . . .
C6 C 0.8271(3) 0.4200(5) 0.60158(17) 0.0569(8) Uani 1 1 d . . . . .
H6 H 0.9226 0.4001 0.6096 0.068 Uiso 1 1 calc R U . . .
C7 C 0.7727(3) 0.4403(5) 0.51926(17) 0.0434(7) Uani 1 1 d . . . . .
C8 C 0.8548(3) 0.4217(4) 0.44364(15) 0.0399(6) Uani 1 1 d . . . . .
C9 C 0.9936(3) 0.4207(5) 0.43087(16) 0.0409(6) Uani 1 1 d . . . . .
C10 C 1.0252(3) 0.4148(5) 0.34034(16) 0.0455(7) Uani 1 1 d . . . . .
C11 C 0.8854(3) 0.4248(5) 0.29201(16) 0.0421(7) Uani 1 1 d . . . . .
C12 C 0.7759(3) 0.4002(4) 0.36110(16) 0.0427(7) Uani 1 1 d . . . . .
H12 H 0.7398 0.2637 0.3579 0.051 Uiso 1 1 calc R U . . .
C13 C 1.1029(3) 0.4309(5) 0.49294(18) 0.0462(7) Uani 1 1 d . . . . .
C14 C 0.8826(4) 0.2552(5) 0.22632(19) 0.0508(9) Uani 1 1 d . . . . .
C15 C 0.9249(4) 0.3299(5) 0.14017(19) 0.0557(9) Uani 1 1 d . . . . .
C16 C 0.9498(4) 0.5510(5) 0.1554(2) 0.0569(9) Uani 1 1 d . . . . .
C17 C 0.8839(4) 0.6132(5) 0.23734(19) 0.0509(9) Uani 1 1 d . . . . .
H17A H 0.7889 0.6595 0.2276 0.061 Uiso 1 1 calc R U . . .
H17B H 0.9375 0.7190 0.2643 0.061 Uiso 1 1 calc R U . . .
C18 C 1.0556(5) 0.2225(6) 0.1091(3) 0.0800(13) Uani 1 1 d . . . . .
H18A H 1.1306 0.2405 0.1494 0.120 Uiso 1 1 calc R U . . .
H18B H 1.0823 0.2767 0.0555 0.120 Uiso 1 1 calc R U . . .
H18C H 1.0361 0.0828 0.1029 0.120 Uiso 1 1 calc R U . . .
C19 C 0.8032(4) 0.2978(6) 0.07520(19) 0.0704(11) Uani 1 1 d . . . . .
H19A H 0.8332 0.3461 0.0206 0.084 Uiso 1 1 calc R U . . .
H19B H 0.7867 0.1557 0.0698 0.084 Uiso 1 1 calc R U . . .
C20 C 0.6668(4) 0.3971(6) 0.09579(18) 0.0635(10) Uani 1 1 d . . . . .
C21 C 0.6359(5) 0.5872(8) 0.0684(2) 0.0842(13) Uani 1 1 d . . . . .
H21 H 0.7006 0.6566 0.0364 0.101 Uiso 1 1 calc R U . . .
C22 C 0.5096(7) 0.6766(9) 0.0880(3) 0.1141(19) Uani 1 1 d . . . . .
H22 H 0.4894 0.8051 0.0695 0.137 Uiso 1 1 calc R U . . .
C23 C 0.4139(6) 0.5717(14) 0.1356(4) 0.119(2) Uani 1 1 d . . . . .
H23 H 0.3290 0.6301 0.1493 0.143 Uiso 1 1 calc R U . . .
C24 C 0.4439(6) 0.3828(11) 0.1623(3) 0.1055(17) Uani 1 1 d . . . . .
H24 H 0.3792 0.3123 0.1939 0.127 Uiso 1 1 calc R U . . .
C25 C 0.5686(5) 0.2976(7) 0.1427(2) 0.0778(12) Uani 1 1 d . . . . .
H25 H 0.5879 0.1690 0.1615 0.093 Uiso 1 1 calc R U . . .
N1 N 1.1935(3) 0.4393(5) 0.54031(18) 0.0664(8) Uani 1 1 d . . . . .
O1 O 0.5648(2) 0.4984(4) 0.43232(15) 0.0659(7) Uani 1 1 d . . . . .
N2 N 1.1415(3) 0.4111(6) 0.30246(18) 0.0659(8) Uani 1 1 d . . . . .
O3 O 0.8486(3) 0.0870(4) 0.24282(15) 0.0800(8) Uani 1 1 d . . . . .
O4 O 1.0106(3) 0.6601(4) 0.10758(17) 0.0868(9) Uani 1 1 d . . . . .
H1N H 1.212(4) 0.413(7) 0.338(2) 0.080(12) Uiso 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
C1 O1 1.430(4) . ?
C1 C12 1.513(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 O1 1.367(4) . ?
C2 C7 1.392(4) . ?
C2 C3 1.393(4) . ?
C3 C4 1.367(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.369(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.370(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.402(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.446(4) . ?
C8 C9 1.345(4) . ?
C8 C12 1.505(4) . ?
C9 C13 1.425(4) . ?
C9 C10 1.468(4) . ?
C10 N2 1.271(4) . ?
C10 C11 1.532(4) . ?
C11 C17 1.531(4) . ?
C11 C12 1.533(4) . ?
C11 C14 1.540(4) . ?
C12 H12 0.9800 . ?
C13 N1 1.138(4) . ?
C14 O3 1.204(4) . ?
C14 C15 1.512(4) . ?
C15 C16 1.520(5) . ?
C15 C18 1.530(5) . ?
C15 C19 1.556(5) . ?
C16 O4 1.207(4) . ?
C16 C17 1.508(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.505(5) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C25 1.378(5) . ?
C20 C21 1.377(6) . ?
C21 C22 1.388(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.384(8) . ?
C22 H22 0.9300 . ?
C23 C24 1.365(8) . ?
C23 H23 0.9300 . ?
C24 C25 1.362(7) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
N2 H1N 0.87(4) . ?

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 C1 C12 110.4(3) . . ?
O1 C1 H1A 109.6 . . ?
C12 C1 H1A 109.6 . . ?
O1 C1 H1B 109.6 . . ?
C12 C1 H1B 109.6 . . ?
H1A C1 H1B 108.1 . . ?
O1 C2 C7 123.6(3) . . ?
O1 C2 C3 116.0(3) . . ?
C7 C2 C3 120.4(3) . . ?
C4 C3 C2 119.4(4) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 121.5(3) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C4 C5 C6 119.5(3) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C5 C6 C7 121.0(3) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C2 C7 C6 118.2(3) . . ?
C2 C7 C8 117.7(3) . . ?
C6 C7 C8 124.1(3) . . ?
C9 C8 C7 132.4(3) . . ?
C9 C8 C12 110.7(2) . . ?
C7 C8 C12 117.0(3) . . ?
C8 C9 C13 127.7(2) . . ?
C8 C9 C10 111.3(2) . . ?
C13 C9 C10 120.9(3) . . ?
N2 C10 C9 130.8(3) . . ?
N2 C10 C11 121.9(3) . . ?
C9 C10 C11 107.2(2) . . ?
C17 C11 C10 108.6(2) . . ?
C17 C11 C12 119.3(2) . . ?
C10 C11 C12 103.9(2) . . ?
C17 C11 C14 103.2(2) . . ?
C10 C11 C14 108.1(2) . . ?
C12 C11 C14 113.3(2) . . ?
C8 C12 C1 108.4(2) . . ?
C8 C12 C11 105.6(2) . . ?
C1 C12 C11 118.8(2) . . ?
C8 C12 H12 107.9 . . ?
C1 C12 H12 107.9 . . ?
C11 C12 H12 107.9 . . ?
N1 C13 C9 177.6(3) . . ?
O3 C14 C15 125.6(3) . . ?
O3 C14 C11 123.2(3) . . ?
C15 C14 C11 111.1(3) . . ?
C14 C15 C16 102.9(3) . . ?
C14 C15 C18 111.3(3) . . ?
C16 C15 C18 112.5(3) . . ?
C14 C15 C19 110.0(3) . . ?
C16 C15 C19 110.7(3) . . ?
C18 C15 C19 109.3(3) . . ?
O4 C16 C17 125.5(3) . . ?
O4 C16 C15 124.6(3) . . ?
C17 C16 C15 109.8(3) . . ?
C16 C17 C11 104.8(3) . . ?
C16 C17 H17A 110.8 . . ?
C11 C17 H17A 110.8 . . ?
C16 C17 H17B 110.8 . . ?
C11 C17 H17B 110.8 . . ?
H17A C17 H17B 108.9 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C15 116.0(3) . . ?
C20 C19 H19A 108.3 . . ?
C15 C19 H19A 108.3 . . ?
C20 C19 H19B 108.3 . . ?
C15 C19 H19B 108.3 . . ?
H19A C19 H19B 107.4 . . ?
C25 C20 C21 118.2(4) . . ?
C25 C20 C19 120.2(4) . . ?
C21 C20 C19 121.6(4) . . ?
C20 C21 C22 120.8(5) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
C23 C22 C21 119.1(6) . . ?
C23 C22 H22 120.5 . . ?
C21 C22 H22 120.5 . . ?
C24 C23 C22 120.2(6) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C25 C24 C23 120.0(5) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C25 C20 121.7(5) . . ?
C24 C25 H25 119.2 . . ?
C20 C25 H25 119.2 . . ?
C2 O1 C1 116.9(3) . . ?
C10 N2 H1N 112(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 178.7(3) . . . . ?
C7 C2 C3 C4 -0.1(5) . . . . ?
C2 C3 C4 C5 1.4(6) . . . . ?
C3 C4 C5 C6 -1.1(6) . . . . ?
C4 C5 C6 C7 -0.5(6) . . . . ?
O1 C2 C7 C6 179.8(3) . . . . ?
C3 C2 C7 C6 -1.4(5) . . . . ?
O1 C2 C7 C8 -1.7(5) . . . . ?
C3 C2 C7 C8 177.0(3) . . . . ?
C5 C6 C7 C2 1.8(5) . . . . ?
C5 C6 C7 C8 -176.5(3) . . . . ?
C2 C7 C8 C9 167.4(3) . . . . ?
C6 C7 C8 C9 -14.3(6) . . . . ?
C2 C7 C8 C12 -12.1(4) . . . . ?
C6 C7 C8 C12 166.2(3) . . . . ?
C7 C8 C9 C13 2.7(6) . . . . ?
C12 C8 C9 C13 -177.7(3) . . . . ?
C7 C8 C9 C10 -175.1(3) . . . . ?
C12 C8 C9 C10 4.4(4) . . . . ?
C8 C9 C10 N2 -179.6(4) . . . . ?
C13 C9 C10 N2 2.4(6) . . . . ?
C8 C9 C10 C11 3.4(4) . . . . ?
C13 C9 C10 C11 -174.6(3) . . . . ?
N2 C10 C11 C17 -58.7(4) . . . . ?
C9 C10 C11 C17 118.6(3) . . . . ?
N2 C10 C11 C12 173.3(3) . . . . ?
C9 C10 C11 C12 -9.4(3) . . . . ?
N2 C10 C11 C14 52.6(4) . . . . ?
C9 C10 C11 C14 -130.0(3) . . . . ?
C9 C8 C12 C1 -138.7(3) . . . . ?
C7 C8 C12 C1 41.0(4) . . . . ?
C9 C8 C12 C11 -10.4(3) . . . . ?
C7 C8 C12 C11 169.3(2) . . . . ?
O1 C1 C12 C8 -57.7(3) . . . . ?
O1 C1 C12 C11 -178.1(2) . . . . ?
C17 C11 C12 C8 -109.4(3) . . . . ?
C10 C11 C12 C8 11.6(3) . . . . ?
C14 C11 C12 C8 128.7(3) . . . . ?
C17 C11 C12 C1 12.4(4) . . . . ?
C10 C11 C12 C1 133.5(3) . . . . ?
C14 C11 C12 C1 -109.5(3) . . . . ?
C17 C11 C14 O3 -161.0(4) . . . . ?
C10 C11 C14 O3 84.1(4) . . . . ?
C12 C11 C14 O3 -30.5(5) . . . . ?
C17 C11 C14 C15 17.9(3) . . . . ?
C10 C11 C14 C15 -97.1(3) . . . . ?
C12 C11 C14 C15 148.4(3) . . . . ?
O3 C14 C15 C16 177.5(4) . . . . ?
C11 C14 C15 C16 -1.4(4) . . . . ?
O3 C14 C15 C18 -61.8(5) . . . . ?
C11 C14 C15 C18 119.4(3) . . . . ?
O3 C14 C15 C19 59.5(5) . . . . ?
C11 C14 C15 C19 -119.3(3) . . . . ?
C14 C15 C16 O4 165.0(3) . . . . ?
C18 C15 C16 O4 45.1(5) . . . . ?
C19 C15 C16 O4 -77.5(5) . . . . ?
C14 C15 C16 C17 -16.5(4) . . . . ?
C18 C15 C16 C17 -136.5(3) . . . . ?
C19 C15 C16 C17 101.0(3) . . . . ?
O4 C16 C17 C11 -153.5(4) . . . . ?
C15 C16 C17 C11 28.1(3) . . . . ?
C10 C11 C17 C16 87.7(3) . . . . ?
C12 C11 C17 C16 -153.7(3) . . . . ?
C14 C11 C17 C16 -26.9(3) . . . . ?
C14 C15 C19 C20 58.4(4) . . . . ?
C16 C15 C19 C20 -54.7(4) . . . . ?
C18 C15 C19 C20 -179.1(3) . . . . ?
C15 C19 C20 C25 -90.0(4) . . . . ?
C15 C19 C20 C21 90.3(4) . . . . ?
C25 C20 C21 C22 0.4(5) . . . . ?
C19 C20 C21 C22 -180.0(4) . . . . ?
C20 C21 C22 C23 -0.2(7) . . . . ?
C21 C22 C23 C24 -0.2(8) . . . . ?
C22 C23 C24 C25 0.4(8) . . . . ?
C23 C24 C25 C20 -0.2(7) . . . . ?
C21 C20 C25 C24 -0.2(6) . . . . ?
C19 C20 C25 C24 -179.8(4) . . . . ?
C7 C2 O1 C1 -17.1(4) . . . . ?
C3 C2 O1 C1 164.2(3) . . . . ?
C12 C1 O1 C2 47.3(4) . . . . ?

_refine_diff_density_max         0.105
_refine_diff_density_min         -0.120
_refine_diff_density_rms         0.028

####################################################################### 
# 
# 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_1147E
_database_code_depnum_ccdc_archive 'CCDC 2096229'
loop_
_audit_author_name
_audit_author_address
'Dr P  K  Sudhadevi Antharjanam'
;Technical Officer SAIF IIT Madras
India
;
_audit_update_record             
;
2021-07-13 deposited with the CCDC.	2022-01-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H24 N2 O3'
_chemical_formula_sum            'C27 H24 N2 O3'
_chemical_formula_weight         424.48

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.7603(4)
_cell_length_b                   7.2351(3)
_cell_length_c                   15.8107(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.4650(10)
_cell_angle_gamma                90
_cell_volume                     1115.47(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)

_cell_measurement_reflns_used    9918
_cell_measurement_theta_min      4.53
_cell_measurement_theta_max      72.32
_exptl_crystal_description       BLOCK
_exptl_crystal_colour            yellow

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.664
_shelx_estimated_absorpt_T_min   0.826
_shelx_estimated_absorpt_T_max   0.879
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6183
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a

_diffrn_radiation_source         'micro-focus sealed tube'
_diffrn_measurement_device_type  'Bruker axs kappa apex3 CMOS Diffractometer'
_diffrn_measurement_method       'ω and φ scan'


_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14745
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.534
_diffrn_reflns_theta_max         72.312
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             4304
_reflns_number_gt                3827
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.832
_reflns_Friedel_fraction_max     0.974
_reflns_Friedel_fraction_full    0.987

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3(Bruker, 2016)'
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'



_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0780P)²+0.0877P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.136(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1556 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.20(13)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         4304
_refine_ls_number_parameters     296
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0484
_refine_ls_wR_factor_ref         0.1386
_refine_ls_wR_factor_gt          0.1314
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8511(3) 0.4281(4) 0.66081(18) 0.0647(7) Uani 1 1 d . . . . .
C2 C 0.9893(3) 0.3977(4) 0.6477(2) 0.0663(7) Uani 1 1 d . . . . .
H2 H 1.050735 0.384154 0.693954 0.080 Uiso 1 1 calc R U . . .
C3 C 1.0359(3) 0.3875(4) 0.5670(2) 0.0634(7) Uani 1 1 d . . . . .
H3 H 1.128741 0.368155 0.559479 0.076 Uiso 1 1 calc R U . . .
C4 C 0.9464(3) 0.4057(4) 0.49577(18) 0.0572(6) Uani 1 1 d . . . . .
C5 C 0.8071(3) 0.4374(4) 0.50906(17) 0.0551(6) Uani 1 1 d . . . . .
C6 C 0.7604(3) 0.4468(5) 0.59211(18) 0.0621(6) Uani 1 1 d . . . . .
H6 H 0.667782 0.465692 0.600589 0.075 Uiso 1 1 calc R U . . .
C7 C 0.7135(3) 0.4588(4) 0.43525(16) 0.0545(6) Uani 1 1 d . . . . .
C8 C 0.7718(3) 0.4765(4) 0.34902(16) 0.0549(6) Uani 1 1 d . . . . .
H8 H 0.807183 0.602647 0.344119 0.066 Uiso 1 1 calc R U . . .
C9 C 0.8921(3) 0.3454(5) 0.3414(2) 0.0658(7) Uani 1 1 d . . . . .
H9A H 0.861590 0.218921 0.348250 0.079 Uiso 1 1 calc R U . . .
H9B H 0.929366 0.357224 0.285766 0.079 Uiso 1 1 calc R U . . .
C10 C 1.0016(3) 0.3914(4) 0.40891(19) 0.0619(7) Uani 1 1 d . . . . .
H10A H 1.071794 0.296472 0.409220 0.074 Uiso 1 1 calc R U . . .
H10B H 1.044254 0.507784 0.394790 0.074 Uiso 1 1 calc R U . . .
C11 C 0.5749(3) 0.4674(4) 0.42906(16) 0.0598(6) Uani 1 1 d . . . . .
C12 C 0.5244(3) 0.4756(5) 0.33977(18) 0.0645(7) Uani 1 1 d . . . . .
C13 C 0.6491(3) 0.4575(4) 0.28541(17) 0.0595(6) Uani 1 1 d . . . . .
C14 C 0.4785(3) 0.4648(6) 0.4941(2) 0.0727(8) Uani 1 1 d . . . . .
C15 C 0.6377(4) 0.2788(5) 0.2333(2) 0.0720(8) Uani 1 1 d . . . . .
H15A H 0.727897 0.228010 0.224156 0.086 Uiso 1 1 calc R U . . .
H15B H 0.584028 0.187048 0.261939 0.086 Uiso 1 1 calc R U . . .
C16 C 0.5678(4) 0.3342(6) 0.1508(2) 0.0788(10) Uani 1 1 d . . . . .
C17 C 0.5890(3) 0.5369(6) 0.1332(2) 0.0760(9) Uani 1 1 d . . . . .
C18 C 0.6418(3) 0.6111(5) 0.2184(2) 0.0662(7) Uani 1 1 d . . . . .
C19 C 0.4565(4) 0.6336(9) 0.1029(3) 0.1030(15) Uani 1 1 d . . . . .
H19A H 0.424442 0.581550 0.049864 0.154 Uiso 1 1 calc R U . . .
H19B H 0.473743 0.763185 0.095874 0.154 Uiso 1 1 calc R U . . .
H19C H 0.388148 0.616754 0.144141 0.154 Uiso 1 1 calc R U . . .
C20 C 0.6987(4) 0.5653(7) 0.0656(2) 0.0881(11) Uani 1 1 d . . . . .
H20A H 0.665743 0.507192 0.013339 0.106 Uiso 1 1 calc R U . . .
H20B H 0.706698 0.696712 0.054696 0.106 Uiso 1 1 calc R U . . .
C21 C 0.8393(3) 0.4908(6) 0.0884(2) 0.0758(9) Uani 1 1 d . . . . .
C22 C 0.8747(5) 0.3114(7) 0.0700(3) 0.0960(13) Uani 1 1 d . . . . .
H22 H 0.810692 0.233252 0.043364 0.115 Uiso 1 1 calc R U . . .
C23 C 1.0062(6) 0.2467(9) 0.0911(4) 0.1174(17) Uani 1 1 d . . . . .
H23 H 1.029197 0.125106 0.078937 0.141 Uiso 1 1 calc R U . . .
C24 C 1.1018(5) 0.3605(10) 0.1296(4) 0.1128(17) Uani 1 1 d . . . . .
H24 H 1.189821 0.316990 0.142853 0.135 Uiso 1 1 calc R U . . .
C25 C 1.0678(4) 0.5380(8) 0.1486(3) 0.1000(13) Uani 1 1 d . . . . .
H25 H 1.132223 0.615319 0.175374 0.120 Uiso 1 1 calc R U . . .
C26 C 0.9382(4) 0.6027(7) 0.1282(3) 0.0845(10) Uani 1 1 d . . . . .
H26 H 0.916222 0.724120 0.141278 0.101 Uiso 1 1 calc R U . . .
C27 C 0.6805(4) 0.4903(7) 0.7593(2) 0.0931(12) Uani 1 1 d . . . . .
H27A H 0.664117 0.613134 0.738212 0.140 Uiso 1 1 calc R U . . .
H27B H 0.667961 0.487910 0.819197 0.140 Uiso 1 1 calc R U . . .
H27C H 0.617264 0.406208 0.731504 0.140 Uiso 1 1 calc R U . . .
N1 N 0.4033(3) 0.4891(6) 0.3088(2) 0.0896(10) Uani 1 1 d . . . . .
N2 N 0.3951(3) 0.4655(8) 0.5430(2) 0.1096(13) Uani 1 1 d . . . . .
O1 O 0.5030(4) 0.2288(6) 0.1040(2) 0.1124(12) Uani 1 1 d . . . . .
O2 O 0.6742(3) 0.7698(4) 0.23302(16) 0.0838(7) Uani 1 1 d . . . . .
O3 O 0.8162(3) 0.4370(4) 0.74317(14) 0.0828(7) Uani 1 1 d . . . . .
H1 H 0.341(5) 0.495(6) 0.353(3) 0.097(13) Uiso 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
C1 O3 1.361(4) . ?
C1 C6 1.378(4) . ?
C1 C2 1.392(5) . ?
C2 C3 1.376(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.401(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.404(4) . ?
C4 C10 1.500(4) . ?
C5 C6 1.410(4) . ?
C5 C7 1.459(4) . ?
C6 H6 0.9300 . ?
C7 C11 1.353(4) . ?
C7 C8 1.505(3) . ?
C8 C9 1.518(4) . ?
C8 C13 1.536(4) . ?
C8 H8 0.9800 . ?
C9 C10 1.515(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C14 1.423(4) . ?
C11 C12 1.476(4) . ?
C12 N1 1.263(4) . ?
C12 C13 1.526(4) . ?
C13 C15 1.535(5) . ?
C13 C18 1.535(4) . ?
C14 N2 1.147(4) . ?
C15 C16 1.501(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 O1 1.219(5) . ?
C16 C17 1.509(6) . ?
C17 C18 1.520(5) . ?
C17 C19 1.528(5) . ?
C17 C20 1.558(5) . ?
C18 O2 1.211(4) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.504(5) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.378(6) . ?
C21 C26 1.390(5) . ?
C22 C23 1.393(7) . ?
C22 H22 0.9300 . ?
C23 C24 1.368(9) . ?
C23 H23 0.9300 . ?
C24 C25 1.363(8) . ?
C24 H24 0.9300 . ?
C25 C26 1.374(6) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 O3 1.414(5) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
N1 H1 0.95(5) . ?

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 C1 C6 124.8(3) . . ?
O3 C1 C2 115.7(3) . . ?
C6 C1 C2 119.5(3) . . ?
C3 C2 C1 120.5(3) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 121.5(3) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C3 C4 C5 118.0(3) . . ?
C3 C4 C10 119.6(2) . . ?
C5 C4 C10 122.4(2) . . ?
C4 C5 C6 120.1(2) . . ?
C4 C5 C7 118.4(2) . . ?
C6 C5 C7 121.6(2) . . ?
C1 C6 C5 120.5(3) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C11 C7 C5 130.7(2) . . ?
C11 C7 C8 110.2(2) . . ?
C5 C7 C8 119.0(2) . . ?
C7 C8 C9 110.0(2) . . ?
C7 C8 C13 105.7(2) . . ?
C9 C8 C13 118.4(2) . . ?
C7 C8 H8 107.4 . . ?
C9 C8 H8 107.4 . . ?
C13 C8 H8 107.4 . . ?
C10 C9 C8 109.4(2) . . ?
C10 C9 H9A 109.8 . . ?
C8 C9 H9A 109.8 . . ?
C10 C9 H9B 109.8 . . ?
C8 C9 H9B 109.8 . . ?
H9A C9 H9B 108.2 . . ?
C4 C10 C9 113.0(2) . . ?
C4 C10 H10A 109.0 . . ?
C9 C10 H10A 109.0 . . ?
C4 C10 H10B 109.0 . . ?
C9 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C7 C11 C14 129.6(2) . . ?
C7 C11 C12 111.3(2) . . ?
C14 C11 C12 119.1(2) . . ?
N1 C12 C11 130.0(3) . . ?
N1 C12 C13 122.9(3) . . ?
C11 C12 C13 107.1(2) . . ?
C12 C13 C15 109.5(3) . . ?
C12 C13 C18 108.2(2) . . ?
C15 C13 C18 103.8(2) . . ?
C12 C13 C8 104.0(2) . . ?
C15 C13 C8 117.6(3) . . ?
C18 C13 C8 113.5(2) . . ?
N2 C14 C11 176.0(4) . . ?
C16 C15 C13 105.1(3) . . ?
C16 C15 H15A 110.7 . . ?
C13 C15 H15A 110.7 . . ?
C16 C15 H15B 110.7 . . ?
C13 C15 H15B 110.7 . . ?
H15A C15 H15B 108.8 . . ?
O1 C16 C15 124.4(4) . . ?
O1 C16 C17 124.6(4) . . ?
C15 C16 C17 111.1(3) . . ?
C16 C17 C18 102.9(3) . . ?
C16 C17 C19 112.4(4) . . ?
C18 C17 C19 111.4(3) . . ?
C16 C17 C20 111.0(3) . . ?
C18 C17 C20 110.1(3) . . ?
C19 C17 C20 108.8(3) . . ?
O2 C18 C17 125.5(3) . . ?
O2 C18 C13 123.4(3) . . ?
C17 C18 C13 111.1(3) . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C17 115.8(3) . . ?
C21 C20 H20A 108.3 . . ?
C17 C20 H20A 108.3 . . ?
C21 C20 H20B 108.3 . . ?
C17 C20 H20B 108.3 . . ?
H20A C20 H20B 107.4 . . ?
C22 C21 C26 117.9(4) . . ?
C22 C21 C20 121.5(4) . . ?
C26 C21 C20 120.6(4) . . ?
C21 C22 C23 120.2(4) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C24 C23 C22 120.5(5) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C25 C24 C23 119.8(5) . . ?
C25 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C24 C25 C26 120.0(5) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C25 C26 C21 121.5(4) . . ?
C25 C26 H26 119.2 . . ?
C21 C26 H26 119.2 . . ?
O3 C27 H27A 109.5 . . ?
O3 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
O3 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C12 N1 H1 109(3) . . ?
C1 O3 C27 117.4(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 C1 C2 C3 -179.6(3) . . . . ?
C6 C1 C2 C3 0.5(4) . . . . ?
C1 C2 C3 C4 -0.5(4) . . . . ?
C2 C3 C4 C5 0.9(4) . . . . ?
C2 C3 C4 C10 -179.3(3) . . . . ?
C3 C4 C5 C6 -1.1(4) . . . . ?
C10 C4 C5 C6 179.0(3) . . . . ?
C3 C4 C5 C7 179.2(2) . . . . ?
C10 C4 C5 C7 -0.6(4) . . . . ?
O3 C1 C6 C5 179.3(3) . . . . ?
C2 C1 C6 C5 -0.7(5) . . . . ?
C4 C5 C6 C1 1.1(4) . . . . ?
C7 C5 C6 C1 -179.3(3) . . . . ?
C4 C5 C7 C11 170.8(3) . . . . ?
C6 C5 C7 C11 -8.8(5) . . . . ?
C4 C5 C7 C8 -9.6(4) . . . . ?
C6 C5 C7 C8 170.8(3) . . . . ?
C11 C7 C8 C9 -140.3(3) . . . . ?
C5 C7 C8 C9 40.0(3) . . . . ?
C11 C7 C8 C13 -11.3(3) . . . . ?
C5 C7 C8 C13 169.0(2) . . . . ?
C7 C8 C9 C10 -59.4(3) . . . . ?
C13 C8 C9 C10 178.9(2) . . . . ?
C3 C4 C10 C9 159.4(3) . . . . ?
C5 C4 C10 C9 -20.7(4) . . . . ?
C8 C9 C10 C4 50.3(3) . . . . ?
C5 C7 C11 C14 2.6(6) . . . . ?
C8 C7 C11 C14 -177.0(3) . . . . ?
C5 C7 C11 C12 -175.6(3) . . . . ?
C8 C7 C11 C12 4.7(4) . . . . ?
C7 C11 C12 N1 -178.1(4) . . . . ?
C14 C11 C12 N1 3.5(6) . . . . ?
C7 C11 C12 C13 3.9(4) . . . . ?
C14 C11 C12 C13 -174.5(3) . . . . ?
N1 C12 C13 C15 -62.2(5) . . . . ?
C11 C12 C13 C15 116.0(3) . . . . ?
N1 C12 C13 C18 50.3(5) . . . . ?
C11 C12 C13 C18 -131.5(3) . . . . ?
N1 C12 C13 C8 171.3(4) . . . . ?
C11 C12 C13 C8 -10.5(3) . . . . ?
C7 C8 C13 C12 12.9(3) . . . . ?
C9 C8 C13 C12 136.8(3) . . . . ?
C7 C8 C13 C15 -108.3(3) . . . . ?
C9 C8 C13 C15 15.6(4) . . . . ?
C7 C8 C13 C18 130.3(3) . . . . ?
C9 C8 C13 C18 -105.9(3) . . . . ?
C12 C13 C15 C16 92.2(3) . . . . ?
C18 C13 C15 C16 -23.1(3) . . . . ?
C8 C13 C15 C16 -149.5(3) . . . . ?
C13 C15 C16 O1 -156.1(4) . . . . ?
C13 C15 C16 C17 24.3(4) . . . . ?
O1 C16 C17 C18 166.0(4) . . . . ?
C15 C16 C17 C18 -14.4(4) . . . . ?
O1 C16 C17 C19 46.0(5) . . . . ?
C15 C16 C17 C19 -134.5(3) . . . . ?
O1 C16 C17 C20 -76.2(5) . . . . ?
C15 C16 C17 C20 103.4(3) . . . . ?
C16 C17 C18 O2 179.0(3) . . . . ?
C19 C17 C18 O2 -60.3(5) . . . . ?
C20 C17 C18 O2 60.6(5) . . . . ?
C16 C17 C18 C13 -1.1(3) . . . . ?
C19 C17 C18 C13 119.6(4) . . . . ?
C20 C17 C18 C13 -119.5(3) . . . . ?
C12 C13 C18 O2 78.9(4) . . . . ?
C15 C13 C18 O2 -164.8(3) . . . . ?
C8 C13 C18 O2 -35.9(4) . . . . ?
C12 C13 C18 C17 -101.0(3) . . . . ?
C15 C13 C18 C17 15.3(3) . . . . ?
C8 C13 C18 C17 144.1(3) . . . . ?
C16 C17 C20 C21 -60.2(5) . . . . ?
C18 C17 C20 C21 53.2(5) . . . . ?
C19 C17 C20 C21 175.6(4) . . . . ?
C17 C20 C21 C22 88.5(5) . . . . ?
C17 C20 C21 C26 -92.2(5) . . . . ?
C26 C21 C22 C23 0.0(6) . . . . ?
C20 C21 C22 C23 179.4(4) . . . . ?
C21 C22 C23 C24 -0.6(8) . . . . ?
C22 C23 C24 C25 0.9(9) . . . . ?
C23 C24 C25 C26 -0.7(8) . . . . ?
C24 C25 C26 C21 0.2(7) . . . . ?
C22 C21 C26 C25 0.2(6) . . . . ?
C20 C21 C26 C25 -179.2(3) . . . . ?
C6 C1 O3 C27 -7.7(5) . . . . ?
C2 C1 O3 C27 172.3(3) . . . . ?

_refine_diff_density_max         0.168
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.036

####################################################################### 
# 
# 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_1756
_database_code_depnum_ccdc_archive 'CCDC 2096231'
loop_
_audit_author_name
_audit_author_address
'Dr P K Sudhadevi Antharjanam'
;Technical Officer SAIF IIT Madras
India
;
_audit_update_record             
;
2021-07-13 deposited with the CCDC.	2022-01-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H20 Cl2 N2 O2'
_chemical_formula_weight         487.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   12.4644(7)
_cell_length_b                   11.8934(6)
_cell_length_c                   15.4819(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2295.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4410
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      23.75

_exptl_crystal_description       BLock
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_F_000             1008
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.313
_shelx_estimated_absorpt_T_min   0.926
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15384
_diffrn_reflns_av_unetI/netI     0.0497
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.712
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4038
_reflns_number_gt                3284
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.917
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.998

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0470P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1307 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.05(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4038
_refine_ls_number_parameters     308
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_ref         0.0920
_refine_ls_wR_factor_gt          0.0835
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0445(3) 0.6703(3) 0.2648(2) 0.0320(8) Uani 1 1 d . . . . .
C2 C 0.1151(3) 0.6026(3) 0.2074(3) 0.0411(10) Uani 1 1 d . . . . .
H2A H 0.1633 0.6516 0.1757 0.049 Uiso 1 1 calc R U . . .
H2B H 0.0721 0.5611 0.1660 0.049 Uiso 1 1 calc R U . . .
C3 C 0.1786(3) 0.5223(3) 0.2626(3) 0.0460(10) Uani 1 1 d . . . . .
H3A H 0.2188 0.4712 0.2260 0.055 Uiso 1 1 calc R U . . .
H3B H 0.2294 0.5641 0.2976 0.055 Uiso 1 1 calc R U . . .
C4 C 0.1053(3) 0.4561(3) 0.3203(3) 0.0392(9) Uani 1 1 d . . . . .
C5 C 0.1243(4) 0.3426(3) 0.3353(3) 0.0512(11) Uani 1 1 d . . . . .
H5 H 0.1842 0.3083 0.3111 0.061 Uiso 1 1 calc R U . . .
C6 C 0.0554(4) 0.2808(4) 0.3856(3) 0.0602(13) Uani 1 1 d . . . . .
H6 H 0.0691 0.2051 0.3959 0.072 Uiso 1 1 calc R U . . .
C7 C -0.0334(4) 0.3307(4) 0.4207(3) 0.0634(13) Uani 1 1 d . . . . .
H7 H -0.0799 0.2883 0.4547 0.076 Uiso 1 1 calc R U . . .
C8 C -0.0548(4) 0.4430(3) 0.4064(3) 0.0492(11) Uani 1 1 d . . . . .
H8 H -0.1165 0.4753 0.4293 0.059 Uiso 1 1 calc R U . . .
C9 C 0.0157(3) 0.5083(3) 0.3578(2) 0.0359(9) Uani 1 1 d . . . . .
C10 C -0.0015(3) 0.6281(3) 0.3366(2) 0.0330(8) Uani 1 1 d . . . . .
C11 C -0.0704(3) 0.7166(3) 0.3751(2) 0.0325(8) Uani 1 1 d . . . . .
C12 C -0.1338(3) 0.7344(3) 0.4474(3) 0.0398(9) Uani 1 1 d . . . . .
C13 C -0.1853(3) 0.9050(4) 0.3982(3) 0.0465(10) Uani 1 1 d . . . . .
H13 H -0.2297 0.9673 0.4046 0.056 Uiso 1 1 calc R U . . .
C14 C -0.0663(3) 0.8103(3) 0.3202(2) 0.0329(8) Uani 1 1 d . . . . .
C15 C 0.0139(3) 0.7907(3) 0.2493(2) 0.0319(8) Uani 1 1 d . . . . .
C16 C -0.0242(3) 0.8211(3) 0.1598(2) 0.0334(8) Uani 1 1 d . . . . .
C17 C 0.0326(3) 0.9044(3) 0.1266(2) 0.0363(9) Uani 1 1 d . . . . .
C18 C 0.1196(3) 0.9524(3) 0.1835(3) 0.0382(9) Uani 1 1 d . . . . .
C19 C 0.1107(3) 0.8731(3) 0.2619(3) 0.0364(9) Uani 1 1 d . . . . .
C20 C -0.1174(3) 0.7641(4) 0.1243(3) 0.0486(11) Uani 1 1 d . . . . .
H20 H -0.1404 0.7823 0.0689 0.058 Uiso 1 1 calc R U . . .
C21 C 0.0906(4) 1.0727(4) 0.2121(3) 0.0601(13) Uani 1 1 d . . . . .
H21A H 0.0221 1.0721 0.2403 0.090 Uiso 1 1 calc R U . . .
H21B H 0.0876 1.1208 0.1624 0.090 Uiso 1 1 calc R U . . .
H21C H 0.1442 1.1000 0.2513 0.090 Uiso 1 1 calc R U . . .
C22 C 0.2345(3) 0.9530(3) 0.1451(3) 0.0488(11) Uani 1 1 d . . . . .
H22A H 0.2339 0.9996 0.0937 0.059 Uiso 1 1 calc R U . . .
H22B H 0.2820 0.9886 0.1865 0.059 Uiso 1 1 calc R U . . .
C23 C 0.2814(3) 0.8408(3) 0.1214(3) 0.0462(10) Uani 1 1 d . . . . .
C24 C 0.2702(4) 0.7965(4) 0.0394(3) 0.0569(11) Uani 1 1 d . . . . .
H24 H 0.2333 0.8372 -0.0024 0.068 Uiso 1 1 calc R U . . .
C25 C 0.3130(4) 0.6928(5) 0.0182(4) 0.0726(15) Uani 1 1 d . . . . .
H25 H 0.3048 0.6642 -0.0374 0.087 Uiso 1 1 calc R U . . .
C26 C 0.3673(4) 0.6326(5) 0.0793(5) 0.0776(16) Uani 1 1 d . . . . .
H26 H 0.3947 0.5620 0.0656 0.093 Uiso 1 1 calc R U . . .
C27 C 0.3816(4) 0.6751(5) 0.1599(4) 0.0733(16) Uani 1 1 d . . . . .
H27 H 0.4201 0.6344 0.2007 0.088 Uiso 1 1 calc R U . . .
C28 C 0.3391(3) 0.7786(4) 0.1813(3) 0.0593(13) Uani 1 1 d . . . . .
H28 H 0.3493 0.8070 0.2367 0.071 Uiso 1 1 calc R U . . .
Cl1 Cl -0.14162(10) 0.64302(11) 0.53379(8) 0.0688(4) Uani 1 1 d . . . . .
Cl2 Cl 0.00731(9) 0.96526(9) 0.02764(8) 0.0565(3) Uani 1 1 d . . . . .
N1 N -0.1930(3) 0.8269(3) 0.4581(2) 0.0439(9) Uani 1 1 d . . . . .
N2 N -0.1209(3) 0.9050(3) 0.3289(2) 0.0408(8) Uani 1 1 d . . . . .
O1 O 0.1662(2) 0.8765(3) 0.32396(19) 0.0562(8) Uani 1 1 d . . . . .
O2 O -0.1656(3) 0.6941(3) 0.1646(2) 0.0864(13) 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
C1 C10 1.348(5) . ?
C1 C2 1.488(5) . ?
C1 C15 1.501(5) . ?
C2 C3 1.507(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.500(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.391(5) . ?
C4 C9 1.403(5) . ?
C5 C6 1.373(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.368(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.381(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.394(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.477(5) . ?
C10 C11 1.484(5) . ?
C11 C12 1.387(5) . ?
C11 C14 1.402(5) . ?
C12 N1 1.334(5) . ?
C12 Cl1 1.726(4) . ?
C13 N1 1.317(5) . ?
C13 N2 1.339(5) . ?
C13 H13 0.9300 . ?
C14 N2 1.323(5) . ?
C14 C15 1.503(5) . ?
C15 C16 1.508(5) . ?
C15 C19 1.566(5) . ?
C16 C17 1.322(5) . ?
C16 C20 1.453(5) . ?
C17 C18 1.509(5) . ?
C17 Cl2 1.724(4) . ?
C18 C21 1.540(6) . ?
C18 C19 1.541(6) . ?
C18 C22 1.551(6) . ?
C19 O1 1.185(5) . ?
C20 O2 1.201(5) . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.502(6) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.382(6) . ?
C23 C28 1.387(6) . ?
C24 C25 1.383(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.366(8) . ?
C25 H25 0.9300 . ?
C26 C27 1.358(8) . ?
C26 H26 0.9300 . ?
C27 C28 1.381(7) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 C1 C2 122.8(3) . . ?
C10 C1 C15 112.3(3) . . ?
C2 C1 C15 124.8(3) . . ?
C1 C2 C3 108.3(3) . . ?
C1 C2 H2A 110.0 . . ?
C3 C2 H2A 110.0 . . ?
C1 C2 H2B 110.0 . . ?
C3 C2 H2B 110.0 . . ?
H2A C2 H2B 108.4 . . ?
C4 C3 C2 110.5(3) . . ?
C4 C3 H3A 109.6 . . ?
C2 C3 H3A 109.6 . . ?
C4 C3 H3B 109.6 . . ?
C2 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?
C5 C4 C9 119.7(4) . . ?
C5 C4 C3 120.3(4) . . ?
C9 C4 C3 120.0(3) . . ?
C6 C5 C4 120.5(4) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C7 C6 C5 120.0(4) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C8 120.8(4) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C7 C8 C9 120.2(4) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C8 C9 C4 118.6(4) . . ?
C8 C9 C10 124.4(4) . . ?
C4 C9 C10 116.7(3) . . ?
C1 C10 C9 118.8(3) . . ?
C1 C10 C11 108.2(3) . . ?
C9 C10 C11 132.8(3) . . ?
C12 C11 C14 112.9(3) . . ?
C12 C11 C10 139.7(4) . . ?
C14 C11 C10 107.4(3) . . ?
N1 C12 C11 122.7(4) . . ?
N1 C12 Cl1 113.1(3) . . ?
C11 C12 Cl1 124.2(3) . . ?
N1 C13 N2 127.4(4) . . ?
N1 C13 H13 116.3 . . ?
N2 C13 H13 116.3 . . ?
N2 C14 C11 126.6(3) . . ?
N2 C14 C15 123.3(3) . . ?
C11 C14 C15 110.1(3) . . ?
C1 C15 C14 101.5(3) . . ?
C1 C15 C16 117.1(3) . . ?
C14 C15 C16 115.1(3) . . ?
C1 C15 C19 112.4(3) . . ?
C14 C15 C19 108.9(3) . . ?
C16 C15 C19 102.0(3) . . ?
C17 C16 C20 129.1(4) . . ?
C17 C16 C15 111.6(3) . . ?
C20 C16 C15 119.2(3) . . ?
C16 C17 C18 116.2(3) . . ?
C16 C17 Cl2 124.2(3) . . ?
C18 C17 Cl2 119.5(3) . . ?
C17 C18 C21 110.5(3) . . ?
C17 C18 C19 100.2(3) . . ?
C21 C18 C19 109.0(3) . . ?
C17 C18 C22 116.1(3) . . ?
C21 C18 C22 108.8(3) . . ?
C19 C18 C22 111.8(3) . . ?
O1 C19 C18 125.1(3) . . ?
O1 C19 C15 125.0(4) . . ?
C18 C19 C15 109.9(3) . . ?
O2 C20 C16 121.8(4) . . ?
O2 C20 H20 119.1 . . ?
C16 C20 H20 119.1 . . ?
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 . . ?
C23 C22 C18 116.7(3) . . ?
C23 C22 H22A 108.1 . . ?
C18 C22 H22A 108.1 . . ?
C23 C22 H22B 108.1 . . ?
C18 C22 H22B 108.1 . . ?
H22A C22 H22B 107.3 . . ?
C24 C23 C28 117.5(4) . . ?
C24 C23 C22 121.6(4) . . ?
C28 C23 C22 120.9(4) . . ?
C23 C24 C25 121.3(5) . . ?
C23 C24 H24 119.3 . . ?
C25 C24 H24 119.3 . . ?
C26 C25 C24 119.6(6) . . ?
C26 C25 H25 120.2 . . ?
C24 C25 H25 120.2 . . ?
C27 C26 C25 120.4(5) . . ?
C27 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
C26 C27 C28 120.2(6) . . ?
C26 C27 H27 119.9 . . ?
C28 C27 H27 119.9 . . ?
C27 C28 C23 120.9(5) . . ?
C27 C28 H28 119.5 . . ?
C23 C28 H28 119.5 . . ?
C13 N1 C12 117.0(3) . . ?
C14 N2 C13 113.0(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 C1 C2 C3 -35.2(5) . . . . ?
C15 C1 C2 C3 146.4(4) . . . . ?
C1 C2 C3 C4 52.4(5) . . . . ?
C2 C3 C4 C5 140.4(4) . . . . ?
C2 C3 C4 C9 -38.2(5) . . . . ?
C9 C4 C5 C6 0.8(7) . . . . ?
C3 C4 C5 C6 -177.8(4) . . . . ?
C4 C5 C6 C7 0.7(8) . . . . ?
C5 C6 C7 C8 -0.2(9) . . . . ?
C6 C7 C8 C9 -1.8(8) . . . . ?
C7 C8 C9 C4 3.2(6) . . . . ?
C7 C8 C9 C10 178.1(4) . . . . ?
C5 C4 C9 C8 -2.7(6) . . . . ?
C3 C4 C9 C8 175.9(4) . . . . ?
C5 C4 C9 C10 -178.0(4) . . . . ?
C3 C4 C9 C10 0.7(5) . . . . ?
C2 C1 C10 C9 -2.1(5) . . . . ?
C15 C1 C10 C9 176.4(3) . . . . ?
C2 C1 C10 C11 -177.1(3) . . . . ?
C15 C1 C10 C11 1.4(4) . . . . ?
C8 C9 C10 C1 -154.0(4) . . . . ?
C4 C9 C10 C1 20.9(5) . . . . ?
C8 C9 C10 C11 19.5(6) . . . . ?
C4 C9 C10 C11 -165.6(4) . . . . ?
C1 C10 C11 C12 -175.7(5) . . . . ?
C9 C10 C11 C12 10.3(8) . . . . ?
C1 C10 C11 C14 2.8(4) . . . . ?
C9 C10 C11 C14 -171.2(4) . . . . ?
C14 C11 C12 N1 6.6(6) . . . . ?
C10 C11 C12 N1 -175.0(4) . . . . ?
C14 C11 C12 Cl1 -171.3(3) . . . . ?
C10 C11 C12 Cl1 7.1(7) . . . . ?
C12 C11 C14 N2 -4.8(5) . . . . ?
C10 C11 C14 N2 176.2(3) . . . . ?
C12 C11 C14 C15 173.1(3) . . . . ?
C10 C11 C14 C15 -5.9(4) . . . . ?
C10 C1 C15 C14 -4.7(4) . . . . ?
C2 C1 C15 C14 173.8(3) . . . . ?
C10 C1 C15 C16 -130.9(4) . . . . ?
C2 C1 C15 C16 47.6(5) . . . . ?
C10 C1 C15 C19 111.5(4) . . . . ?
C2 C1 C15 C19 -70.0(5) . . . . ?
N2 C14 C15 C1 -175.6(3) . . . . ?
C11 C14 C15 C1 6.4(4) . . . . ?
N2 C14 C15 C16 -48.2(5) . . . . ?
C11 C14 C15 C16 133.8(3) . . . . ?
N2 C14 C15 C19 65.7(4) . . . . ?
C11 C14 C15 C19 -112.3(3) . . . . ?
C1 C15 C16 C17 -124.9(4) . . . . ?
C14 C15 C16 C17 115.9(4) . . . . ?
C19 C15 C16 C17 -1.8(4) . . . . ?
C1 C15 C16 C20 58.8(5) . . . . ?
C14 C15 C16 C20 -60.4(5) . . . . ?
C19 C15 C16 C20 -178.1(3) . . . . ?
C20 C16 C17 C18 174.7(4) . . . . ?
C15 C16 C17 C18 -1.1(5) . . . . ?
C20 C16 C17 Cl2 -1.0(6) . . . . ?
C15 C16 C17 Cl2 -176.8(3) . . . . ?
C16 C17 C18 C21 -111.3(4) . . . . ?
Cl2 C17 C18 C21 64.6(4) . . . . ?
C16 C17 C18 C19 3.6(4) . . . . ?
Cl2 C17 C18 C19 179.4(3) . . . . ?
C16 C17 C18 C22 124.2(4) . . . . ?
Cl2 C17 C18 C22 -60.0(4) . . . . ?
C17 C18 C19 O1 178.0(4) . . . . ?
C21 C18 C19 O1 -66.0(5) . . . . ?
C22 C18 C19 O1 54.4(5) . . . . ?
C17 C18 C19 C15 -4.5(4) . . . . ?
C21 C18 C19 C15 111.5(4) . . . . ?
C22 C18 C19 C15 -128.2(3) . . . . ?
C1 C15 C19 O1 -52.2(5) . . . . ?
C14 C15 C19 O1 59.4(5) . . . . ?
C16 C15 C19 O1 -178.4(4) . . . . ?
C1 C15 C19 C18 130.3(3) . . . . ?
C14 C15 C19 C18 -118.1(3) . . . . ?
C16 C15 C19 C18 4.1(4) . . . . ?
C17 C16 C20 O2 -174.9(5) . . . . ?
C15 C16 C20 O2 0.7(7) . . . . ?
C17 C18 C22 C23 -60.4(5) . . . . ?
C21 C18 C22 C23 174.2(4) . . . . ?
C19 C18 C22 C23 53.7(5) . . . . ?
C18 C22 C23 C24 91.8(5) . . . . ?
C18 C22 C23 C28 -89.2(5) . . . . ?
C28 C23 C24 C25 1.4(6) . . . . ?
C22 C23 C24 C25 -179.6(4) . . . . ?
C23 C24 C25 C26 0.0(7) . . . . ?
C24 C25 C26 C27 -1.5(8) . . . . ?
C25 C26 C27 C28 1.5(8) . . . . ?
C26 C27 C28 C23 0.0(7) . . . . ?
C24 C23 C28 C27 -1.4(6) . . . . ?
C22 C23 C28 C27 179.6(4) . . . . ?
N2 C13 N1 C12 -3.2(6) . . . . ?
C11 C12 N1 C13 -3.1(6) . . . . ?
Cl1 C12 N1 C13 175.0(3) . . . . ?
C11 C14 N2 C13 -0.4(6) . . . . ?
C15 C14 N2 C13 -178.1(3) . . . . ?
N1 C13 N2 C14 4.9(6) . . . . ?

_refine_diff_density_max         0.152
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.041

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2096230'
loop_
_audit_author_name
_audit_author_address
'Dr P K Sudhadevi Antharjanam'
;Technical Officer SAIF IIT Madras
India
;
_audit_update_record             
;
2021-07-13 deposited with the CCDC.	2022-01-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H22 N2 O2 S'
_chemical_formula_sum            'C26 H22 N2 O2 S'
_chemical_formula_weight         426.51

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   11.4340(12)
_cell_length_b                   10.0679(10)
_cell_length_c                   19.338(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.571(6)
_cell_angle_gamma                90
_cell_volume                     2172.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)

_cell_measurement_reflns_used    2634
_cell_measurement_theta_min      2.16
_cell_measurement_theta_max      20.09
_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colourless

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_F_000             896
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.175
_shelx_estimated_absorpt_T_min   0.949
_shelx_estimated_absorpt_T_max   0.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6243
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   'SADABS (bruker, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker axs kappa apex2 Diffractometer'
_diffrn_measurement_method       'ω and φ scan'


_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20693
_diffrn_reflns_av_unetI/netI     0.0686
_diffrn_reflns_av_R_equivalents  0.0751
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.825
_diffrn_reflns_theta_max         25.899
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4204
_reflns_number_gt                2213
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'

_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'


_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0503P)²+0.3789P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0107(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4204
_refine_ls_number_parameters     287
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1206
_refine_ls_R_factor_gt           0.0525
_refine_ls_wR_factor_ref         0.1400
_refine_ls_wR_factor_gt          0.1071
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2773(3) 0.7635(3) 0.53123(14) 0.0493(7) Uani 1 1 d . . . . .
C2 C 0.1829(3) 0.7568(3) 0.47198(16) 0.0658(9) Uani 1 1 d . . . . .
H2 H 0.193084 0.790211 0.428834 0.079 Uiso 1 1 calc R U . . .
C3 C 0.0750(3) 0.7015(3) 0.47660(18) 0.0704(10) Uani 1 1 d . . . . .
H3 H 0.012858 0.697875 0.436604 0.084 Uiso 1 1 calc R U . . .
C4 C 0.0581(3) 0.6516(3) 0.53964(17) 0.0654(9) Uani 1 1 d . . . . .
H4 H -0.015294 0.614671 0.542448 0.078 Uiso 1 1 calc R U . . .
C5 C 0.1498(3) 0.6563(3) 0.59855(15) 0.0527(8) Uani 1 1 d . . . . .
H5 H 0.137579 0.622261 0.641129 0.063 Uiso 1 1 calc R U . . .
C6 C 0.2614(2) 0.7111(3) 0.59614(13) 0.0410(7) Uani 1 1 d . . . . .
C7 C 0.3599(2) 0.7071(2) 0.65750(13) 0.0381(6) Uani 1 1 d . . . . .
C8 C 0.4873(2) 0.7207(2) 0.64853(13) 0.0409(7) Uani 1 1 d . . . . .
H8 H 0.505957 0.643744 0.621851 0.049 Uiso 1 1 calc R U . . .
C9 C 0.4989(3) 0.8451(3) 0.60618(14) 0.0514(8) Uani 1 1 d . . . . .
H9A H 0.582251 0.857457 0.604136 0.062 Uiso 1 1 calc R U . . .
H9B H 0.474250 0.921559 0.630012 0.062 Uiso 1 1 calc R U . . .
C10 C 0.3580(2) 0.6930(2) 0.72678(13) 0.0398(7) Uani 1 1 d . . . . .
C11 C 0.4780(2) 0.6937(2) 0.77178(14) 0.0440(7) Uani 1 1 d . . . . .
C12 C 0.5673(2) 0.7145(2) 0.72416(13) 0.0388(6) Uani 1 1 d . . . . .
C13 C 0.6513(2) 0.8308(2) 0.75078(14) 0.0475(7) Uani 1 1 d . . . . .
H13A H 0.667256 0.881478 0.711168 0.057 Uiso 1 1 calc R U . . .
H13B H 0.615471 0.889480 0.780189 0.057 Uiso 1 1 calc R U . . .
C14 C 0.7649(3) 0.7718(3) 0.79298(15) 0.0521(8) Uani 1 1 d . . . . .
C15 C 0.7741(2) 0.6249(3) 0.77628(14) 0.0447(7) Uani 1 1 d . . . . .
C16 C 0.6499(2) 0.5913(3) 0.73503(13) 0.0414(7) Uani 1 1 d . . . . .
C17 C 0.8658(3) 0.6051(3) 0.72902(15) 0.0597(8) Uani 1 1 d . . . . .
H17A H 0.943314 0.636917 0.754516 0.072 Uiso 1 1 calc R U . . .
H17B H 0.873382 0.510800 0.720794 0.072 Uiso 1 1 calc R U . . .
C18 C 0.8341(3) 0.6750(3) 0.65815(18) 0.0586(8) Uani 1 1 d . . . . .
C19 C 0.8707(3) 0.8047(4) 0.6507(2) 0.0848(12) Uani 1 1 d . . . . .
H19 H 0.918871 0.848632 0.688740 0.102 Uiso 1 1 calc R U . . .
C20 C 0.8344(5) 0.8685(4) 0.5853(3) 0.1056(16) Uani 1 1 d . . . . .
H20 H 0.857210 0.955977 0.580095 0.127 Uiso 1 1 calc R U . . .
C21 C 0.7655(4) 0.8028(4) 0.5292(3) 0.0984(15) Uani 1 1 d . . . . .
H21 H 0.742557 0.846603 0.486020 0.118 Uiso 1 1 calc R U . . .
C22 C 0.7292(3) 0.6739(4) 0.53459(18) 0.0734(10) Uani 1 1 d . . . . .
C23 C 0.7652(3) 0.6109(3) 0.60011(16) 0.0605(9) Uani 1 1 d . . . . .
H23 H 0.742222 0.523391 0.604849 0.073 Uiso 1 1 calc R U . . .
C24 C 0.6556(4) 0.6011(4) 0.47260(18) 0.1083(15) Uani 1 1 d . . . . .
H24A H 0.591281 0.657095 0.448919 0.162 Uiso 1 1 calc R U . . .
H24B H 0.623190 0.521984 0.488868 0.162 Uiso 1 1 calc R U . . .
H24C H 0.705122 0.577600 0.440270 0.162 Uiso 1 1 calc R U . . .
C25 C 0.8099(3) 0.5405(3) 0.84381(15) 0.0685(9) Uani 1 1 d . . . . .
H25A H 0.749642 0.548300 0.871224 0.103 Uiso 1 1 calc R U . . .
H25B H 0.885290 0.571193 0.871310 0.103 Uiso 1 1 calc R U . . .
H25C H 0.817213 0.449150 0.831066 0.103 Uiso 1 1 calc R U . . .
C26 C 0.2579(3) 0.6837(3) 0.75897(15) 0.0528(8) Uani 1 1 d . . . . .
N1 N 0.1839(3) 0.6750(3) 0.78990(14) 0.0828(9) Uani 1 1 d . . . . .
N2 N 0.5148(3) 0.6789(3) 0.83820(14) 0.0598(8) Uani 1 1 d . . . . .
O1 O 0.61637(17) 0.48208(18) 0.71354(10) 0.0551(6) Uani 1 1 d . . . . .
O2 O 0.8400(2) 0.8340(2) 0.83344(12) 0.0818(7) Uani 1 1 d . . . . .
S1 S 0.40942(8) 0.83587(9) 0.51775(4) 0.0706(3) Uani 1 1 d . . . . .
H2A H 0.458(3) 0.674(3) 0.8578(17) 0.078(13) Uiso 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
C1 C2 1.394(4) . ?
C1 C6 1.409(4) . ?
C1 S1 1.748(3) . ?
C2 C3 1.375(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.370(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.371(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.400(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.448(3) . ?
C7 C10 1.352(3) . ?
C7 C8 1.510(3) . ?
C8 C9 1.518(3) . ?
C8 C12 1.548(3) . ?
C8 H8 0.9800 . ?
C9 S1 1.794(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C26 1.420(4) . ?
C10 C11 1.456(4) . ?
C11 N2 1.270(3) . ?
C11 C12 1.531(4) . ?
C12 C13 1.531(3) . ?
C12 C16 1.546(3) . ?
C13 C14 1.499(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 O2 1.204(3) . ?
C14 C15 1.522(4) . ?
C15 C16 1.508(4) . ?
C15 C25 1.537(4) . ?
C15 C17 1.546(4) . ?
C16 O1 1.208(3) . ?
C17 C18 1.513(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C23 1.383(4) . ?
C18 C19 1.388(4) . ?
C19 C20 1.398(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.366(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.374(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.396(4) . ?
C22 C24 1.498(5) . ?
C23 H23 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 N1 1.141(4) . ?
N2 H2A 0.82(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
C2 C1 C6 119.2(3) . . ?
C2 C1 S1 115.9(2) . . ?
C6 C1 S1 124.9(2) . . ?
C3 C2 C1 120.7(3) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C4 C3 C2 120.6(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 119.7(3) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 121.6(3) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C5 C6 C1 118.2(2) . . ?
C5 C6 C7 120.9(2) . . ?
C1 C6 C7 120.8(2) . . ?
C10 C7 C6 129.6(2) . . ?
C10 C7 C8 110.3(2) . . ?
C6 C7 C8 120.1(2) . . ?
C7 C8 C9 109.7(2) . . ?
C7 C8 C12 105.9(2) . . ?
C9 C8 C12 116.1(2) . . ?
C7 C8 H8 108.3 . . ?
C9 C8 H8 108.3 . . ?
C12 C8 H8 108.3 . . ?
C8 C9 S1 111.89(18) . . ?
C8 C9 H9A 109.2 . . ?
S1 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
S1 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C7 C10 C26 129.0(3) . . ?
C7 C10 C11 112.0(2) . . ?
C26 C10 C11 118.9(2) . . ?
N2 C11 C10 131.7(3) . . ?
N2 C11 C12 120.4(3) . . ?
C10 C11 C12 107.8(2) . . ?
C13 C12 C11 110.7(2) . . ?
C13 C12 C16 104.4(2) . . ?
C11 C12 C16 106.0(2) . . ?
C13 C12 C8 119.0(2) . . ?
C11 C12 C8 103.9(2) . . ?
C16 C12 C8 112.3(2) . . ?
C14 C13 C12 106.6(2) . . ?
C14 C13 H13A 110.4 . . ?
C12 C13 H13A 110.4 . . ?
C14 C13 H13B 110.4 . . ?
C12 C13 H13B 110.4 . . ?
H13A C13 H13B 108.6 . . ?
O2 C14 C13 123.9(3) . . ?
O2 C14 C15 124.8(3) . . ?
C13 C14 C15 111.2(2) . . ?
C16 C15 C14 103.2(2) . . ?
C16 C15 C25 111.8(2) . . ?
C14 C15 C25 112.0(2) . . ?
C16 C15 C17 109.9(2) . . ?
C14 C15 C17 109.7(2) . . ?
C25 C15 C17 110.0(2) . . ?
O1 C16 C15 125.3(2) . . ?
O1 C16 C12 123.0(2) . . ?
C15 C16 C12 111.7(2) . . ?
C18 C17 C15 114.6(2) . . ?
C18 C17 H17A 108.6 . . ?
C15 C17 H17A 108.6 . . ?
C18 C17 H17B 108.6 . . ?
C15 C17 H17B 108.6 . . ?
H17A C17 H17B 107.6 . . ?
C23 C18 C19 119.0(3) . . ?
C23 C18 C17 120.0(3) . . ?
C19 C18 C17 120.9(3) . . ?
C18 C19 C20 119.3(4) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C21 C20 C19 120.1(4) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C20 C21 C22 121.9(4) . . ?
C20 C21 H21 119.0 . . ?
C22 C21 H21 119.0 . . ?
C21 C22 C23 117.6(4) . . ?
C21 C22 C24 121.9(4) . . ?
C23 C22 C24 120.5(4) . . ?
C18 C23 C22 121.9(3) . . ?
C18 C23 H23 119.1 . . ?
C22 C23 H23 119.1 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C15 C25 H25A 109.5 . . ?
C15 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C15 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N1 C26 C10 174.5(3) . . ?
C11 N2 H2A 111(2) . . ?
C1 S1 C9 102.24(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.8(4) . . . . ?
S1 C1 C2 C3 179.8(3) . . . . ?
C1 C2 C3 C4 -0.1(5) . . . . ?
C2 C3 C4 C5 -0.3(5) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
C4 C5 C6 C1 0.8(4) . . . . ?
C4 C5 C6 C7 -175.7(3) . . . . ?
C2 C1 C6 C5 -1.1(4) . . . . ?
S1 C1 C6 C5 179.9(2) . . . . ?
C2 C1 C6 C7 175.3(2) . . . . ?
S1 C1 C6 C7 -3.6(4) . . . . ?
C5 C6 C7 C10 -21.9(4) . . . . ?
C1 C6 C7 C10 161.7(3) . . . . ?
C5 C6 C7 C8 158.5(2) . . . . ?
C1 C6 C7 C8 -17.8(4) . . . . ?
C10 C7 C8 C9 -126.6(2) . . . . ?
C6 C7 C8 C9 53.0(3) . . . . ?
C10 C7 C8 C12 -0.6(3) . . . . ?
C6 C7 C8 C12 179.0(2) . . . . ?
C7 C8 C9 S1 -63.8(3) . . . . ?
C12 C8 C9 S1 176.22(18) . . . . ?
C6 C7 C10 C26 -3.0(4) . . . . ?
C8 C7 C10 C26 176.6(3) . . . . ?
C6 C7 C10 C11 179.8(2) . . . . ?
C8 C7 C10 C11 -0.6(3) . . . . ?
C7 C10 C11 N2 -177.3(3) . . . . ?
C26 C10 C11 N2 5.1(4) . . . . ?
C7 C10 C11 C12 1.5(3) . . . . ?
C26 C10 C11 C12 -176.0(2) . . . . ?
N2 C11 C12 C13 -53.9(3) . . . . ?
C10 C11 C12 C13 127.1(2) . . . . ?
N2 C11 C12 C16 58.8(3) . . . . ?
C10 C11 C12 C16 -120.3(2) . . . . ?
N2 C11 C12 C8 177.2(2) . . . . ?
C10 C11 C12 C8 -1.8(3) . . . . ?
C7 C8 C12 C13 -122.2(2) . . . . ?
C9 C8 C12 C13 -0.2(3) . . . . ?
C7 C8 C12 C11 1.4(2) . . . . ?
C9 C8 C12 C11 123.4(2) . . . . ?
C7 C8 C12 C16 115.6(2) . . . . ?
C9 C8 C12 C16 -122.5(2) . . . . ?
C11 C12 C13 C14 98.3(2) . . . . ?
C16 C12 C13 C14 -15.4(3) . . . . ?
C8 C12 C13 C14 -141.5(2) . . . . ?
C12 C13 C14 O2 -163.9(3) . . . . ?
C12 C13 C14 C15 17.9(3) . . . . ?
O2 C14 C15 C16 169.5(3) . . . . ?
C13 C14 C15 C16 -12.2(3) . . . . ?
O2 C14 C15 C25 49.1(4) . . . . ?
C13 C14 C15 C25 -132.6(3) . . . . ?
O2 C14 C15 C17 -73.4(4) . . . . ?
C13 C14 C15 C17 104.9(3) . . . . ?
C14 C15 C16 O1 -177.0(2) . . . . ?
C25 C15 C16 O1 -56.4(4) . . . . ?
C17 C15 C16 O1 66.0(3) . . . . ?
C14 C15 C16 C12 2.0(3) . . . . ?
C25 C15 C16 C12 122.5(2) . . . . ?
C17 C15 C16 C12 -115.0(2) . . . . ?
C13 C12 C16 O1 -172.7(2) . . . . ?
C11 C12 C16 O1 70.3(3) . . . . ?
C8 C12 C16 O1 -42.5(3) . . . . ?
C13 C12 C16 C15 8.4(3) . . . . ?
C11 C12 C16 C15 -108.6(2) . . . . ?
C8 C12 C16 C15 138.6(2) . . . . ?
C16 C15 C17 C18 51.8(3) . . . . ?
C14 C15 C17 C18 -61.1(3) . . . . ?
C25 C15 C17 C18 175.3(3) . . . . ?
C15 C17 C18 C23 -89.4(3) . . . . ?
C15 C17 C18 C19 88.9(4) . . . . ?
C23 C18 C19 C20 1.7(5) . . . . ?
C17 C18 C19 C20 -176.6(3) . . . . ?
C18 C19 C20 C21 -1.2(6) . . . . ?
C19 C20 C21 C22 0.4(7) . . . . ?
C20 C21 C22 C23 0.0(6) . . . . ?
C20 C21 C22 C24 -178.8(4) . . . . ?
C19 C18 C23 C22 -1.4(5) . . . . ?
C17 C18 C23 C22 176.9(3) . . . . ?
C21 C22 C23 C18 0.5(5) . . . . ?
C24 C22 C23 C18 179.4(3) . . . . ?
C2 C1 S1 C9 172.9(2) . . . . ?
C6 C1 S1 C9 -8.1(3) . . . . ?
C8 C9 S1 C1 41.1(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C2 H2 N1 0.93 2.69 3.590(4) 163.4 4_575 yes
C9 H9B N2 0.97 2.66 3.543(4) 151.5 2_656 yes
C2 H2 N1 0.93 2.69 3.590(4) 163.4 4_575 yes
C9 H9B N2 0.97 2.66 3.543(4) 151.5 2_656 yes

_refine_diff_density_max         0.203
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.045

