# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_GRK_6_190722_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2201656'
loop_
_audit_author_name
_audit_author_address
'Sherin Anto'
;Vellore Institute of technology, vellore
India
;
_audit_update_record             
;
2022-08-16 deposited with the CCDC.	2025-06-12 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         'C19 H16 N2 O3'
_chemical_formula_sum            'C19 H16 N2 O3'
_chemical_formula_weight         320.34

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   7.7786(6)
_cell_length_b                   14.2417(11)
_cell_length_c                   14.3928(11)
_cell_angle_alpha                85.179(2)
_cell_angle_beta                 87.476(3)
_cell_angle_gamma                79.599(2)
_cell_volume                     1562.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    9883
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      28.24

_exptl_crystal_description       block
_exptl_crystal_colour            gold
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6900
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'i-mu-s microfocus source'
_diffrn_measurement_device_type  
'Bruker D8 QUEST diffractometer with PHOTON II detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            43249
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.842
_diffrn_reflns_theta_max         28.287
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             7715
_reflns_number_gt                5408
_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       'Bruker APEX4'
_computing_cell_refinement       'Bruker APEX4/SAINT'
_computing_data_reduction        'Bruker APEX4/SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0615P)²+0.4147P] 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_number_reflns         7715
_refine_ls_number_parameters     439
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0532
_refine_ls_wR_factor_ref         0.1456
_refine_ls_wR_factor_gt          0.1276
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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
O1_1 O 0.56583(15) 0.13039(7) 0.22265(7) 0.0445(3) Uani 1 1 d . . . . .
O2_1 O 1.07243(17) 0.23054(9) -0.30237(8) 0.0594(3) Uani 1 1 d . . . . .
O3_1 O 0.69223(19) 0.01191(8) 0.14216(9) 0.0658(4) Uani 1 1 d . . . . .
N1_1 N 0.69873(16) 0.33318(9) 0.02000(9) 0.0389(3) Uani 1 1 d . . . . .
N2_1 N 0.2757(2) 0.36799(11) 0.41546(10) 0.0598(4) Uani 1 1 d . . . . .
C1_1 C 0.79126(18) 0.30220(10) -0.05727(10) 0.0372(3) Uani 1 1 d . . . . .
C2_1 C 0.8361(2) 0.37146(12) -0.12645(11) 0.0470(4) Uani 1 1 d . . . . .
H2_1 H 0.801532 0.436231 -0.117910 0.056 Uiso 1 1 calc R U . . .
C3_1 C 0.9286(2) 0.34453(12) -0.20480(12) 0.0491(4) Uani 1 1 d . . . . .
H3_1 H 0.956649 0.391132 -0.249177 0.059 Uiso 1 1 calc R U . . .
C4_1 C 0.9829(2) 0.24688(12) -0.22009(11) 0.0445(4) Uani 1 1 d . . . . .
C5_1 C 0.9436(2) 0.17761(11) -0.15502(11) 0.0429(4) Uani 1 1 d . . . . .
H5_1 H 0.980661 0.113258 -0.164660 0.051 Uiso 1 1 calc R U . . .
C6_1 C 0.84648(18) 0.20417(11) -0.07314(10) 0.0373(3) Uani 1 1 d . . . . .
C7_1 C 0.65734(17) 0.26720(10) 0.08397(10) 0.0335(3) Uani 1 1 d . . . . .
C8_1 C 0.70599(18) 0.16805(10) 0.07393(10) 0.0361(3) Uani 1 1 d . . . . .
C9_1 C 0.80037(19) 0.13700(10) -0.00405(10) 0.0400(3) Uani 1 1 d . . . . .
H9_1 H 0.833460 0.071814 -0.010955 0.048 Uiso 1 1 calc R U . . .
C10_1 C 0.55864(18) 0.29635(10) 0.16770(10) 0.0346(3) Uani 1 1 d . . . . .
C11_1 C 0.51561(18) 0.22721(10) 0.23393(10) 0.0357(3) Uani 1 1 d . . . . .
C12_1 C 0.6576(2) 0.09728(11) 0.14566(11) 0.0428(4) Uani 1 1 d . . . . .
C13_1 C 0.5033(2) 0.39170(11) 0.18759(11) 0.0443(4) Uani 1 1 d . . . . .
H13_1 H 0.529145 0.440273 0.144872 0.053 Uiso 1 1 calc R U . . .
C14_1 C 0.4117(2) 0.41551(12) 0.26846(12) 0.0493(4) Uani 1 1 d . . . . .
H14_1 H 0.377525 0.479690 0.279581 0.059 Uiso 1 1 calc R U . . .
C15_1 C 0.3687(2) 0.34427(12) 0.33501(10) 0.0432(4) Uani 1 1 d . . . . .
C16_1 C 0.4224(2) 0.24880(11) 0.31542(10) 0.0407(3) Uani 1 1 d . . . . .
H16_1 H 0.395348 0.199853 0.357308 0.049 Uiso 1 1 calc R U . . .
C17_1 C 1.1153(3) 0.13400(14) -0.32583(14) 0.0677(5) Uani 1 1 d . . . . .
H17A_1 H 1.171830 0.131856 -0.386457 0.102 Uiso 1 1 calc R U . . .
H17B_1 H 1.010406 0.107411 -0.326360 0.102 Uiso 1 1 calc R U . . .
H17C_1 H 1.192583 0.097497 -0.280530 0.102 Uiso 1 1 calc R U . . .
C18_1 C 0.2526(3) 0.46414(16) 0.44396(15) 0.0803(7) Uani 1 1 d . . . . .
H18A_1 H 0.206521 0.465319 0.506914 0.120 Uiso 1 1 calc R U . . .
H18B_1 H 0.172628 0.505928 0.403418 0.120 Uiso 1 1 calc R U . . .
H18C_1 H 0.363303 0.485266 0.440535 0.120 Uiso 1 1 calc R U . . .
C19_1 C 0.2350(2) 0.29382(16) 0.48318(12) 0.0623(5) Uani 1 1 d . . . . .
H19A_1 H 0.163389 0.322471 0.532952 0.093 Uiso 1 1 calc R U . . .
H19B_1 H 0.341374 0.257265 0.507868 0.093 Uiso 1 1 calc R U . . .
H19C_1 H 0.173057 0.252422 0.453729 0.093 Uiso 1 1 calc R U . . .
O1_2 O 0.21191(15) 0.62927(7) 0.58754(7) 0.0482(3) Uani 1 1 d . . . . .
O2_2 O -0.35552(16) 0.72705(10) 1.09896(8) 0.0590(3) Uani 1 1 d . . . . .
O3_2 O 0.15264(19) 0.51051(8) 0.68312(9) 0.0631(4) Uani 1 1 d . . . . .
N1_2 N -0.03193(16) 0.83136(9) 0.76592(9) 0.0398(3) Uani 1 1 d . . . . .
N2_2 N 0.3749(2) 0.86608(12) 0.36602(11) 0.0663(4) Uani 1 1 d . . . . .
C1_2 C -0.10925(18) 0.80069(11) 0.84666(10) 0.0384(3) Uani 1 1 d . . . . .
C2_2 C -0.10430(18) 0.70258(11) 0.87570(10) 0.0380(3) Uani 1 1 d . . . . .
C3_2 C -0.18565(19) 0.67565(12) 0.96144(10) 0.0430(4) Uani 1 1 d . . . . .
H3_2 H -0.180739 0.611211 0.980500 0.052 Uiso 1 1 calc R U . . .
C4_2 C -0.27098(19) 0.74409(12) 1.01589(11) 0.0441(4) Uani 1 1 d . . . . .
C5_2 C -0.2777(2) 0.84197(13) 0.98699(12) 0.0498(4) Uani 1 1 d . . . . .
H5_2 H -0.336447 0.888349 1.024458 0.060 Uiso 1 1 calc R U . . .
C6_2 C -0.1998(2) 0.86944(12) 0.90532(11) 0.0471(4) Uani 1 1 d . . . . .
H6_2 H -0.206118 0.934281 0.887716 0.057 Uiso 1 1 calc R U . . .
C7_2 C 0.04863(18) 0.76573(10) 0.71091(10) 0.0355(3) Uani 1 1 d . . . . .
C8_2 C 0.05635(18) 0.66631(10) 0.73336(10) 0.0366(3) Uani 1 1 d . . . . .
C9_2 C -0.01820(19) 0.63566(11) 0.81573(10) 0.0406(3) Uani 1 1 d . . . . .
H9_2 H -0.011628 0.570499 0.831776 0.049 Uiso 1 1 calc R U . . .
C10_2 C 0.13215(18) 0.79496(10) 0.62350(10) 0.0366(3) Uani 1 1 d . . . . .
C11_2 C 0.20975(19) 0.72602(10) 0.56475(10) 0.0379(3) Uani 1 1 d . . . . .
C12_2 C 0.1413(2) 0.59572(11) 0.66965(11) 0.0435(4) Uani 1 1 d . . . . .
C13_2 C 0.1411(2) 0.88950(11) 0.59312(12) 0.0483(4) Uani 1 1 d . . . . .
H13_2 H 0.091681 0.937979 0.630656 0.058 Uiso 1 1 calc R U . . .
C14_2 C 0.2205(2) 0.91346(12) 0.50959(13) 0.0549(4) Uani 1 1 d . . . . .
H14_2 H 0.224071 0.977436 0.491977 0.066 Uiso 1 1 calc R U . . .
C15_2 C 0.2967(2) 0.84258(12) 0.45006(11) 0.0475(4) Uani 1 1 d . . . . .
C16_2 C 0.2891(2) 0.74740(12) 0.48015(11) 0.0444(4) Uani 1 1 d . . . . .
H16_2 H 0.337666 0.698471 0.442946 0.053 Uiso 1 1 calc R U . . .
C17_2 C -0.3558(3) 0.62959(15) 1.13032(14) 0.0651(5) Uani 1 1 d . . . . .
H17A_2 H -0.420800 0.626582 1.188430 0.098 Uiso 1 1 calc R U . . .
H17B_2 H -0.237695 0.596956 1.138971 0.098 Uiso 1 1 calc R U . . .
H17C_2 H -0.409064 0.599508 1.084709 0.098 Uiso 1 1 calc R U . . .
C18_2 C 0.4462(3) 0.79301(16) 0.30402(13) 0.0667(5) Uani 1 1 d . . . . .
H18A_2 H 0.486985 0.822549 0.246852 0.100 Uiso 1 1 calc R U . . .
H18B_2 H 0.357087 0.757734 0.290945 0.100 Uiso 1 1 calc R U . . .
H18C_2 H 0.541940 0.750225 0.333104 0.100 Uiso 1 1 calc R U . . .
C19_2 C 0.3827(3) 0.96486(16) 0.33627(17) 0.0861(7) Uani 1 1 d . . . . .
H19A_2 H 0.445843 0.967814 0.277581 0.129 Uiso 1 1 calc R U . . .
H19B_2 H 0.441214 0.991836 0.382077 0.129 Uiso 1 1 calc R U . . .
H19C_2 H 0.266196 1.000467 0.329424 0.129 Uiso 1 1 calc R U . . .


_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_1 C12_1 1.3627(18) . ?
O1_1 C11_1 1.3848(17) . ?
O2_1 C4_1 1.3626(19) . ?
O2_1 C17_1 1.421(2) . ?
O3_1 C12_1 1.2017(18) . ?
N1_1 C7_1 1.3312(18) . ?
N1_1 C1_1 1.3589(19) . ?
N2_1 C15_1 1.372(2) . ?
N2_1 C18_1 1.440(2) . ?
N2_1 C19_1 1.445(2) . ?
C1_1 C6_1 1.419(2) . ?
C1_1 C2_1 1.419(2) . ?
C2_1 C3_1 1.356(2) . ?
C2_1 H2_1 0.9300 . ?
C3_1 C4_1 1.411(2) . ?
C3_1 H3_1 0.9300 . ?
C4_1 C5_1 1.368(2) . ?
C5_1 C6_1 1.413(2) . ?
C5_1 H5_1 0.9300 . ?
C6_1 C9_1 1.402(2) . ?
C7_1 C8_1 1.412(2) . ?
C7_1 C10_1 1.450(2) . ?
C8_1 C9_1 1.374(2) . ?
C8_1 C12_1 1.467(2) . ?
C9_1 H9_1 0.9300 . ?
C10_1 C11_1 1.387(2) . ?
C10_1 C13_1 1.398(2) . ?
C11_1 C16_1 1.379(2) . ?
C13_1 C14_1 1.372(2) . ?
C13_1 H13_1 0.9300 . ?
C14_1 C15_1 1.411(2) . ?
C14_1 H14_1 0.9300 . ?
C15_1 C16_1 1.397(2) . ?
C16_1 H16_1 0.9300 . ?
C17_1 H17A_1 0.9600 . ?
C17_1 H17B_1 0.9600 . ?
C17_1 H17C_1 0.9600 . ?
C18_1 H18A_1 0.9600 . ?
C18_1 H18B_1 0.9600 . ?
C18_1 H18C_1 0.9600 . ?
C19_1 H19A_1 0.9600 . ?
C19_1 H19B_1 0.9600 . ?
C19_1 H19C_1 0.9600 . ?
O1_2 C12_2 1.3673(18) . ?
O1_2 C11_2 1.3866(18) . ?
O2_2 C4_2 1.3640(19) . ?
O2_2 C17_2 1.423(2) . ?
O3_2 C12_2 1.2005(19) . ?
N1_2 C7_2 1.3276(18) . ?
N1_2 C1_2 1.3605(19) . ?
N2_2 C15_2 1.373(2) . ?
N2_2 C18_2 1.446(3) . ?
N2_2 C19_2 1.447(3) . ?
C1_2 C6_2 1.416(2) . ?
C1_2 C2_2 1.419(2) . ?
C2_2 C9_2 1.400(2) . ?
C2_2 C3_2 1.418(2) . ?
C3_2 C4_2 1.362(2) . ?
C3_2 H3_2 0.9300 . ?
C4_2 C5_2 1.413(2) . ?
C5_2 C6_2 1.359(2) . ?
C5_2 H5_2 0.9300 . ?
C6_2 H6_2 0.9300 . ?
C7_2 C8_2 1.417(2) . ?
C7_2 C10_2 1.455(2) . ?
C8_2 C9_2 1.370(2) . ?
C8_2 C12_2 1.466(2) . ?
C9_2 H9_2 0.9300 . ?
C10_2 C11_2 1.387(2) . ?
C10_2 C13_2 1.393(2) . ?
C11_2 C16_2 1.377(2) . ?
C13_2 C14_2 1.373(2) . ?
C13_2 H13_2 0.9300 . ?
C14_2 C15_2 1.410(2) . ?
C14_2 H14_2 0.9300 . ?
C15_2 C16_2 1.399(2) . ?
C16_2 H16_2 0.9300 . ?
C17_2 H17A_2 0.9600 . ?
C17_2 H17B_2 0.9600 . ?
C17_2 H17C_2 0.9600 . ?
C18_2 H18A_2 0.9600 . ?
C18_2 H18B_2 0.9600 . ?
C18_2 H18C_2 0.9600 . ?
C19_2 H19A_2 0.9600 . ?
C19_2 H19B_2 0.9600 . ?
C19_2 H19C_2 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
C12_1 O1_1 C11_1 122.32(11) . . ?
C4_1 O2_1 C17_1 117.07(13) . . ?
C7_1 N1_1 C1_1 117.63(12) . . ?
C15_1 N2_1 C18_1 120.41(16) . . ?
C15_1 N2_1 C19_1 120.22(15) . . ?
C18_1 N2_1 C19_1 117.84(15) . . ?
N1_1 C1_1 C6_1 123.85(13) . . ?
N1_1 C1_1 C2_1 118.47(14) . . ?
C6_1 C1_1 C2_1 117.68(14) . . ?
C3_1 C2_1 C1_1 120.93(15) . . ?
C3_1 C2_1 H2_1 119.5 . . ?
C1_1 C2_1 H2_1 119.5 . . ?
C2_1 C3_1 C4_1 121.04(15) . . ?
C2_1 C3_1 H3_1 119.5 . . ?
C4_1 C3_1 H3_1 119.5 . . ?
O2_1 C4_1 C5_1 125.36(15) . . ?
O2_1 C4_1 C3_1 114.58(14) . . ?
C5_1 C4_1 C3_1 120.06(15) . . ?
C4_1 C5_1 C6_1 119.79(15) . . ?
C4_1 C5_1 H5_1 120.1 . . ?
C6_1 C5_1 H5_1 120.1 . . ?
C9_1 C6_1 C5_1 122.77(14) . . ?
C9_1 C6_1 C1_1 116.73(13) . . ?
C5_1 C6_1 C1_1 120.50(13) . . ?
N1_1 C7_1 C8_1 122.48(13) . . ?
N1_1 C7_1 C10_1 119.88(13) . . ?
C8_1 C7_1 C10_1 117.64(12) . . ?
C9_1 C8_1 C7_1 119.73(13) . . ?
C9_1 C8_1 C12_1 119.22(13) . . ?
C7_1 C8_1 C12_1 121.05(13) . . ?
C8_1 C9_1 C6_1 119.59(13) . . ?
C8_1 C9_1 H9_1 120.2 . . ?
C6_1 C9_1 H9_1 120.2 . . ?
C11_1 C10_1 C13_1 116.42(13) . . ?
C11_1 C10_1 C7_1 119.56(13) . . ?
C13_1 C10_1 C7_1 124.01(13) . . ?
C16_1 C11_1 O1_1 115.11(13) . . ?
C16_1 C11_1 C10_1 123.24(14) . . ?
O1_1 C11_1 C10_1 121.65(13) . . ?
O3_1 C12_1 O1_1 116.95(13) . . ?
O3_1 C12_1 C8_1 125.27(14) . . ?
O1_1 C12_1 C8_1 117.78(13) . . ?
C14_1 C13_1 C10_1 121.74(15) . . ?
C14_1 C13_1 H13_1 119.1 . . ?
C10_1 C13_1 H13_1 119.1 . . ?
C13_1 C14_1 C15_1 121.11(15) . . ?
C13_1 C14_1 H14_1 119.4 . . ?
C15_1 C14_1 H14_1 119.4 . . ?
N2_1 C15_1 C16_1 121.28(15) . . ?
N2_1 C15_1 C14_1 121.17(15) . . ?
C16_1 C15_1 C14_1 117.54(14) . . ?
C11_1 C16_1 C15_1 119.94(14) . . ?
C11_1 C16_1 H16_1 120.0 . . ?
C15_1 C16_1 H16_1 120.0 . . ?
O2_1 C17_1 H17A_1 109.5 . . ?
O2_1 C17_1 H17B_1 109.5 . . ?
H17A_1 C17_1 H17B_1 109.5 . . ?
O2_1 C17_1 H17C_1 109.5 . . ?
H17A_1 C17_1 H17C_1 109.5 . . ?
H17B_1 C17_1 H17C_1 109.5 . . ?
N2_1 C18_1 H18A_1 109.5 . . ?
N2_1 C18_1 H18B_1 109.5 . . ?
H18A_1 C18_1 H18B_1 109.5 . . ?
N2_1 C18_1 H18C_1 109.5 . . ?
H18A_1 C18_1 H18C_1 109.5 . . ?
H18B_1 C18_1 H18C_1 109.5 . . ?
N2_1 C19_1 H19A_1 109.5 . . ?
N2_1 C19_1 H19B_1 109.5 . . ?
H19A_1 C19_1 H19B_1 109.5 . . ?
N2_1 C19_1 H19C_1 109.5 . . ?
H19A_1 C19_1 H19C_1 109.5 . . ?
H19B_1 C19_1 H19C_1 109.5 . . ?
C12_2 O1_2 C11_2 122.37(12) . . ?
C4_2 O2_2 C17_2 116.98(14) . . ?
C7_2 N1_2 C1_2 117.93(13) . . ?
C15_2 N2_2 C18_2 120.75(16) . . ?
C15_2 N2_2 C19_2 120.68(17) . . ?
C18_2 N2_2 C19_2 118.54(16) . . ?
N1_2 C1_2 C6_2 118.95(14) . . ?
N1_2 C1_2 C2_2 123.34(13) . . ?
C6_2 C1_2 C2_2 117.71(14) . . ?
C9_2 C2_2 C3_2 122.68(14) . . ?
C9_2 C2_2 C1_2 116.96(13) . . ?
C3_2 C2_2 C1_2 120.36(14) . . ?
C4_2 C3_2 C2_2 120.02(15) . . ?
C4_2 C3_2 H3_2 120.0 . . ?
C2_2 C3_2 H3_2 120.0 . . ?
C3_2 C4_2 O2_2 125.36(16) . . ?
C3_2 C4_2 C5_2 119.91(15) . . ?
O2_2 C4_2 C5_2 114.73(14) . . ?
C6_2 C5_2 C4_2 121.07(15) . . ?
C6_2 C5_2 H5_2 119.5 . . ?
C4_2 C5_2 H5_2 119.5 . . ?
C5_2 C6_2 C1_2 120.92(16) . . ?
C5_2 C6_2 H6_2 119.5 . . ?
C1_2 C6_2 H6_2 119.5 . . ?
N1_2 C7_2 C8_2 122.50(13) . . ?
N1_2 C7_2 C10_2 119.99(13) . . ?
C8_2 C7_2 C10_2 117.51(13) . . ?
C9_2 C8_2 C7_2 119.37(14) . . ?
C9_2 C8_2 C12_2 119.43(14) . . ?
C7_2 C8_2 C12_2 121.19(13) . . ?
C8_2 C9_2 C2_2 119.87(14) . . ?
C8_2 C9_2 H9_2 120.1 . . ?
C2_2 C9_2 H9_2 120.1 . . ?
C11_2 C10_2 C13_2 116.08(14) . . ?
C11_2 C10_2 C7_2 119.52(13) . . ?
C13_2 C10_2 C7_2 124.41(14) . . ?
C16_2 C11_2 O1_2 114.90(13) . . ?
C16_2 C11_2 C10_2 123.37(14) . . ?
O1_2 C11_2 C10_2 121.72(13) . . ?
O3_2 C12_2 O1_2 116.98(14) . . ?
O3_2 C12_2 C8_2 125.38(14) . . ?
O1_2 C12_2 C8_2 117.64(13) . . ?
C14_2 C13_2 C10_2 122.17(16) . . ?
C14_2 C13_2 H13_2 118.9 . . ?
C10_2 C13_2 H13_2 118.9 . . ?
C13_2 C14_2 C15_2 121.04(16) . . ?
C13_2 C14_2 H14_2 119.5 . . ?
C15_2 C14_2 H14_2 119.5 . . ?
N2_2 C15_2 C16_2 121.41(16) . . ?
N2_2 C15_2 C14_2 121.37(16) . . ?
C16_2 C15_2 C14_2 117.22(15) . . ?
C11_2 C16_2 C15_2 120.11(15) . . ?
C11_2 C16_2 H16_2 119.9 . . ?
C15_2 C16_2 H16_2 119.9 . . ?
O2_2 C17_2 H17A_2 109.5 . . ?
O2_2 C17_2 H17B_2 109.5 . . ?
H17A_2 C17_2 H17B_2 109.5 . . ?
O2_2 C17_2 H17C_2 109.5 . . ?
H17A_2 C17_2 H17C_2 109.5 . . ?
H17B_2 C17_2 H17C_2 109.5 . . ?
N2_2 C18_2 H18A_2 109.5 . . ?
N2_2 C18_2 H18B_2 109.5 . . ?
H18A_2 C18_2 H18B_2 109.5 . . ?
N2_2 C18_2 H18C_2 109.5 . . ?
H18A_2 C18_2 H18C_2 109.5 . . ?
H18B_2 C18_2 H18C_2 109.5 . . ?
N2_2 C19_2 H19A_2 109.5 . . ?
N2_2 C19_2 H19B_2 109.5 . . ?
H19A_2 C19_2 H19B_2 109.5 . . ?
N2_2 C19_2 H19C_2 109.5 . . ?
H19A_2 C19_2 H19C_2 109.5 . . ?
H19B_2 C19_2 H19C_2 109.5 . . ?

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
C7_1 N1_1 C1_1 C6_1 -0.3(2) . . . . ?
C7_1 N1_1 C1_1 C2_1 179.76(13) . . . . ?
N1_1 C1_1 C2_1 C3_1 179.86(15) . . . . ?
C6_1 C1_1 C2_1 C3_1 0.0(2) . . . . ?
C1_1 C2_1 C3_1 C4_1 0.1(3) . . . . ?
C17_1 O2_1 C4_1 C5_1 5.6(2) . . . . ?
C17_1 O2_1 C4_1 C3_1 -173.92(15) . . . . ?
C2_1 C3_1 C4_1 O2_1 179.08(15) . . . . ?
C2_1 C3_1 C4_1 C5_1 -0.5(2) . . . . ?
O2_1 C4_1 C5_1 C6_1 -178.68(14) . . . . ?
C3_1 C4_1 C5_1 C6_1 0.8(2) . . . . ?
C4_1 C5_1 C6_1 C9_1 179.43(14) . . . . ?
C4_1 C5_1 C6_1 C1_1 -0.8(2) . . . . ?
N1_1 C1_1 C6_1 C9_1 0.3(2) . . . . ?
C2_1 C1_1 C6_1 C9_1 -179.82(13) . . . . ?
N1_1 C1_1 C6_1 C5_1 -179.50(13) . . . . ?
C2_1 C1_1 C6_1 C5_1 0.4(2) . . . . ?
C1_1 N1_1 C7_1 C8_1 0.0(2) . . . . ?
C1_1 N1_1 C7_1 C10_1 -179.96(12) . . . . ?
N1_1 C7_1 C8_1 C9_1 0.3(2) . . . . ?
C10_1 C7_1 C8_1 C9_1 -179.68(13) . . . . ?
N1_1 C7_1 C8_1 C12_1 -179.77(13) . . . . ?
C10_1 C7_1 C8_1 C12_1 0.2(2) . . . . ?
C7_1 C8_1 C9_1 C6_1 -0.4(2) . . . . ?
C12_1 C8_1 C9_1 C6_1 179.72(14) . . . . ?
C5_1 C6_1 C9_1 C8_1 179.87(14) . . . . ?
C1_1 C6_1 C9_1 C8_1 0.1(2) . . . . ?
N1_1 C7_1 C10_1 C11_1 179.84(13) . . . . ?
C8_1 C7_1 C10_1 C11_1 -0.15(19) . . . . ?
N1_1 C7_1 C10_1 C13_1 -0.7(2) . . . . ?
C8_1 C7_1 C10_1 C13_1 179.28(14) . . . . ?
C12_1 O1_1 C11_1 C16_1 179.55(13) . . . . ?
C12_1 O1_1 C11_1 C10_1 -1.0(2) . . . . ?
C13_1 C10_1 C11_1 C16_1 0.4(2) . . . . ?
C7_1 C10_1 C11_1 C16_1 179.91(13) . . . . ?
C13_1 C10_1 C11_1 O1_1 -178.93(13) . . . . ?
C7_1 C10_1 C11_1 O1_1 0.5(2) . . . . ?
C11_1 O1_1 C12_1 O3_1 -178.86(14) . . . . ?
C11_1 O1_1 C12_1 C8_1 1.1(2) . . . . ?
C9_1 C8_1 C12_1 O3_1 -0.8(3) . . . . ?
C7_1 C8_1 C12_1 O3_1 179.25(16) . . . . ?
C9_1 C8_1 C12_1 O1_1 179.23(13) . . . . ?
C7_1 C8_1 C12_1 O1_1 -0.7(2) . . . . ?
C11_1 C10_1 C13_1 C14_1 0.2(2) . . . . ?
C7_1 C10_1 C13_1 C14_1 -179.25(14) . . . . ?
C10_1 C13_1 C14_1 C15_1 -0.4(3) . . . . ?
C18_1 N2_1 C15_1 C16_1 167.11(17) . . . . ?
C19_1 N2_1 C15_1 C16_1 1.5(2) . . . . ?
C18_1 N2_1 C15_1 C14_1 -13.7(3) . . . . ?
C19_1 N2_1 C15_1 C14_1 -179.22(16) . . . . ?
C13_1 C14_1 C15_1 N2_1 -179.35(15) . . . . ?
C13_1 C14_1 C15_1 C16_1 -0.1(2) . . . . ?
O1_1 C11_1 C16_1 C15_1 178.51(13) . . . . ?
C10_1 C11_1 C16_1 C15_1 -0.9(2) . . . . ?
N2_1 C15_1 C16_1 C11_1 179.95(14) . . . . ?
C14_1 C15_1 C16_1 C11_1 0.7(2) . . . . ?
C7_2 N1_2 C1_2 C6_2 -178.39(13) . . . . ?
C7_2 N1_2 C1_2 C2_2 1.6(2) . . . . ?
N1_2 C1_2 C2_2 C9_2 -1.6(2) . . . . ?
C6_2 C1_2 C2_2 C9_2 178.36(13) . . . . ?
N1_2 C1_2 C2_2 C3_2 179.08(13) . . . . ?
C6_2 C1_2 C2_2 C3_2 -1.0(2) . . . . ?
C9_2 C2_2 C3_2 C4_2 -178.48(14) . . . . ?
C1_2 C2_2 C3_2 C4_2 0.8(2) . . . . ?
C2_2 C3_2 C4_2 O2_2 179.24(14) . . . . ?
C2_2 C3_2 C4_2 C5_2 -0.2(2) . . . . ?
C17_2 O2_2 C4_2 C3_2 -0.8(2) . . . . ?
C17_2 O2_2 C4_2 C5_2 178.71(14) . . . . ?
C3_2 C4_2 C5_2 C6_2 -0.1(2) . . . . ?
O2_2 C4_2 C5_2 C6_2 -179.66(14) . . . . ?
C4_2 C5_2 C6_2 C1_2 -0.1(2) . . . . ?
N1_2 C1_2 C6_2 C5_2 -179.44(14) . . . . ?
C2_2 C1_2 C6_2 C5_2 0.6(2) . . . . ?
C1_2 N1_2 C7_2 C8_2 0.0(2) . . . . ?
C1_2 N1_2 C7_2 C10_2 179.54(12) . . . . ?
N1_2 C7_2 C8_2 C9_2 -1.5(2) . . . . ?
C10_2 C7_2 C8_2 C9_2 178.96(13) . . . . ?
N1_2 C7_2 C8_2 C12_2 177.93(13) . . . . ?
C10_2 C7_2 C8_2 C12_2 -1.6(2) . . . . ?
C7_2 C8_2 C9_2 C2_2 1.4(2) . . . . ?
C12_2 C8_2 C9_2 C2_2 -178.03(13) . . . . ?
C3_2 C2_2 C9_2 C8_2 179.34(14) . . . . ?
C1_2 C2_2 C9_2 C8_2 0.0(2) . . . . ?
N1_2 C7_2 C10_2 C11_2 -177.38(13) . . . . ?
C8_2 C7_2 C10_2 C11_2 2.2(2) . . . . ?
N1_2 C7_2 C10_2 C13_2 2.7(2) . . . . ?
C8_2 C7_2 C10_2 C13_2 -177.70(14) . . . . ?
C12_2 O1_2 C11_2 C16_2 178.96(13) . . . . ?
C12_2 O1_2 C11_2 C10_2 -1.3(2) . . . . ?
C13_2 C10_2 C11_2 C16_2 -1.2(2) . . . . ?
C7_2 C10_2 C11_2 C16_2 178.91(14) . . . . ?
C13_2 C10_2 C11_2 O1_2 179.10(13) . . . . ?
C7_2 C10_2 C11_2 O1_2 -0.8(2) . . . . ?
C11_2 O1_2 C12_2 O3_2 -178.83(14) . . . . ?
C11_2 O1_2 C12_2 C8_2 1.9(2) . . . . ?
C9_2 C8_2 C12_2 O3_2 -0.2(3) . . . . ?
C7_2 C8_2 C12_2 O3_2 -179.60(16) . . . . ?
C9_2 C8_2 C12_2 O1_2 179.08(13) . . . . ?
C7_2 C8_2 C12_2 O1_2 -0.4(2) . . . . ?
C11_2 C10_2 C13_2 C14_2 0.6(2) . . . . ?
C7_2 C10_2 C13_2 C14_2 -179.53(15) . . . . ?
C10_2 C13_2 C14_2 C15_2 0.3(3) . . . . ?
C18_2 N2_2 C15_2 C16_2 2.4(3) . . . . ?
C19_2 N2_2 C15_2 C16_2 -179.57(18) . . . . ?
C18_2 N2_2 C15_2 C14_2 -177.48(17) . . . . ?
C19_2 N2_2 C15_2 C14_2 0.5(3) . . . . ?
C13_2 C14_2 C15_2 N2_2 179.38(17) . . . . ?
C13_2 C14_2 C15_2 C16_2 -0.5(3) . . . . ?
O1_2 C11_2 C16_2 C15_2 -179.32(13) . . . . ?
C10_2 C11_2 C16_2 C15_2 1.0(2) . . . . ?
N2_2 C15_2 C16_2 C11_2 -179.97(15) . . . . ?
C14_2 C15_2 C16_2 C11_2 -0.1(2) . . . . ?

_refine_diff_density_max         0.267
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.035

####################################################################### 
# 
# 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_GRK_1_070922_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2208633'
loop_
_audit_author_name
_audit_author_address
'Sherin Anto'
;Vellore Institute of technology, vellore
India
;
_audit_update_record             
;
2022-09-21 deposited with the CCDC.	2025-06-12 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         'C16 H8 N2 O4'
_chemical_formula_sum            'C16 H8 N2 O4'
_chemical_formula_weight         292.24

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           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.822(3)
_cell_length_b                   5.4227(16)
_cell_length_c                   23.386(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.596(10)
_cell_angle_gamma                90
_cell_volume                     1228.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    5465
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      29.57

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.117
_shelx_estimated_absorpt_T_min   0.963
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6586
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   
;
SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'i-mu-s microfocus source'
_diffrn_measurement_device_type  
'Bruker D8 Quest diffractometer with PHOTON II detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13368
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.141
_diffrn_reflns_theta_max         26.316
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2474
_reflns_number_gt                1807
_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       'Bruker APEX4'
_computing_cell_refinement       'Bruker APEX4/SAINT'
_computing_data_reduction        'Bruker APEX4/SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0482P)²+0.4730P] 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_number_reflns         2474
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1138
_refine_ls_wR_factor_gt          0.0966
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_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
O1 O 0.20590(16) 0.0541(3) 0.70602(6) 0.0730(5) Uani 1 1 d . . . . .
O2 O 0.21479(11) 0.9567(2) 0.35826(5) 0.0409(3) Uani 1 1 d . . . . .
O3 O 0.06791(12) 1.0727(2) 0.41458(5) 0.0480(4) Uani 1 1 d . . . . .
O4 O 0.06007(15) 0.3505(3) 0.68664(6) 0.0641(4) Uani 1 1 d . . . . .
N1 N 0.35124(13) 0.3633(3) 0.46609(6) 0.0336(3) Uani 1 1 d . . . . .
N3 N 0.15348(16) 0.2208(3) 0.67519(7) 0.0463(4) Uani 1 1 d . . . . .
C1 C 0.45376(18) 0.6798(4) 0.27447(8) 0.0425(4) Uani 1 1 d . . . . .
H1 H 0.488450 0.712532 0.240603 0.051 Uiso 1 1 calc R U . . .
C2 C 0.36007(17) 0.8395(3) 0.29233(7) 0.0401(4) Uani 1 1 d . . . . .
H2 H 0.330933 0.979186 0.270642 0.048 Uiso 1 1 calc R U . . .
C3 C 0.30983(16) 0.7888(3) 0.34311(7) 0.0335(4) Uani 1 1 d . . . . .
C4 C 0.15549(16) 0.9263(3) 0.40646(7) 0.0350(4) Uani 1 1 d . . . . .
C5 C 0.20368(15) 0.7203(3) 0.44539(7) 0.0316(4) Uani 1 1 d . . . . .
C6 C 0.30286(15) 0.5492(3) 0.43148(7) 0.0304(4) Uani 1 1 d . . . . .
C7 C 0.15312(15) 0.6933(3) 0.49626(7) 0.0345(4) Uani 1 1 d . . . . .
H7 H 0.087283 0.802420 0.505729 0.041 Uiso 1 1 calc R U . . .
C8 C 0.20179(15) 0.4993(3) 0.53389(7) 0.0322(4) Uani 1 1 d . . . . .
C9 C 0.30208(15) 0.3376(3) 0.51685(7) 0.0311(4) Uani 1 1 d . . . . .
C10 C 0.35247(16) 0.1407(3) 0.55419(7) 0.0365(4) Uani 1 1 d . . . . .
H10 H 0.419123 0.035191 0.543992 0.044 Uiso 1 1 calc R U . . .
C11 C 0.30432(17) 0.1039(3) 0.60499(7) 0.0388(4) Uani 1 1 d . . . . .
H11 H 0.336954 -0.026921 0.629138 0.047 Uiso 1 1 calc R U . . .
C12 C 0.20495(16) 0.2660(3) 0.62039(7) 0.0354(4) Uani 1 1 d . . . . .
C13 C 0.15399(16) 0.4604(3) 0.58711(7) 0.0358(4) Uani 1 1 d . . . . .
H13 H 0.089248 0.565598 0.598919 0.043 Uiso 1 1 calc R U . . .
C15 C 0.35335(15) 0.5849(3) 0.37692(7) 0.0314(4) Uani 1 1 d . . . . .
C16 C 0.44699(17) 0.4243(3) 0.35725(7) 0.0390(4) Uani 1 1 d . . . . .
H16 H 0.476170 0.283935 0.378700 0.047 Uiso 1 1 calc R U . . .
C17 C 0.49668(18) 0.4709(3) 0.30656(8) 0.0432(5) Uani 1 1 d . . . . .
H17 H 0.558804 0.362517 0.293951 0.052 Uiso 1 1 calc R U . . .


_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 N3 1.216(2) . ?
O2 C4 1.3622(19) . ?
O2 C3 1.3914(19) . ?
O3 C4 1.2085(19) . ?
O4 N3 1.221(2) . ?
N1 C6 1.330(2) . ?
N1 C9 1.361(2) . ?
N3 C12 1.474(2) . ?
C1 C2 1.378(2) . ?
C1 C17 1.385(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.387(2) . ?
C2 H2 0.9300 . ?
C3 C15 1.385(2) . ?
C4 C5 1.469(2) . ?
C5 C7 1.371(2) . ?
C5 C6 1.422(2) . ?
C6 C15 1.457(2) . ?
C7 C8 1.403(2) . ?
C7 H7 0.9300 . ?
C8 C13 1.417(2) . ?
C8 C9 1.424(2) . ?
C9 C10 1.416(2) . ?
C10 C11 1.364(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.404(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.356(2) . ?
C13 H13 0.9300 . ?
C15 C16 1.399(2) . ?
C16 C17 1.379(2) . ?
C16 H16 0.9300 . ?
C17 H17 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
C4 O2 C3 121.95(13) . . ?
C6 N1 C9 117.75(13) . . ?
O1 N3 O4 123.90(15) . . ?
O1 N3 C12 117.78(15) . . ?
O4 N3 C12 118.32(16) . . ?
C2 C1 C17 120.52(16) . . ?
C2 C1 H1 119.7 . . ?
C17 C1 H1 119.7 . . ?
C1 C2 C3 119.07(16) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C15 C3 C2 121.78(15) . . ?
C15 C3 O2 122.23(14) . . ?
C2 C3 O2 115.98(15) . . ?
O3 C4 O2 117.67(15) . . ?
O3 C4 C5 124.50(15) . . ?
O2 C4 C5 117.82(13) . . ?
C7 C5 C6 119.33(15) . . ?
C7 C5 C4 119.54(14) . . ?
C6 C5 C4 121.13(14) . . ?
N1 C6 C5 122.98(14) . . ?
N1 C6 C15 119.63(14) . . ?
C5 C6 C15 117.39(14) . . ?
C5 C7 C8 119.29(14) . . ?
C5 C7 H7 120.4 . . ?
C8 C7 H7 120.4 . . ?
C7 C8 C13 122.30(15) . . ?
C7 C8 C9 117.72(14) . . ?
C13 C8 C9 119.98(15) . . ?
N1 C9 C10 118.48(14) . . ?
N1 C9 C8 122.92(15) . . ?
C10 C9 C8 118.60(14) . . ?
C11 C10 C9 120.73(15) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 119.25(16) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C13 C12 C11 123.05(15) . . ?
C13 C12 N3 118.73(15) . . ?
C11 C12 N3 118.22(16) . . ?
C12 C13 C8 118.38(15) . . ?
C12 C13 H13 120.8 . . ?
C8 C13 H13 120.8 . . ?
C3 C15 C16 117.82(15) . . ?
C3 C15 C6 119.22(14) . . ?
C16 C15 C6 122.95(15) . . ?
C17 C16 C15 120.99(17) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C16 C17 C1 119.78(16) . . ?
C16 C17 H17 120.1 . . ?
C1 C17 H17 120.1 . . ?

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
C17 C1 C2 C3 0.3(3) . . . . ?
C1 C2 C3 C15 1.3(3) . . . . ?
C1 C2 C3 O2 -179.49(15) . . . . ?
C4 O2 C3 C15 -2.1(2) . . . . ?
C4 O2 C3 C2 178.74(14) . . . . ?
C3 O2 C4 O3 -175.68(14) . . . . ?
C3 O2 C4 C5 5.2(2) . . . . ?
O3 C4 C5 C7 -3.4(3) . . . . ?
O2 C4 C5 C7 175.70(14) . . . . ?
O3 C4 C5 C6 177.15(16) . . . . ?
O2 C4 C5 C6 -3.8(2) . . . . ?
C9 N1 C6 C5 0.3(2) . . . . ?
C9 N1 C6 C15 179.54(14) . . . . ?
C7 C5 C6 N1 -0.9(2) . . . . ?
C4 C5 C6 N1 178.58(14) . . . . ?
C7 C5 C6 C15 179.85(14) . . . . ?
C4 C5 C6 C15 -0.7(2) . . . . ?
C6 C5 C7 C8 0.9(2) . . . . ?
C4 C5 C7 C8 -178.61(14) . . . . ?
C5 C7 C8 C13 -179.93(15) . . . . ?
C5 C7 C8 C9 -0.3(2) . . . . ?
C6 N1 C9 C10 179.98(14) . . . . ?
C6 N1 C9 C8 0.3(2) . . . . ?
C7 C8 C9 N1 -0.3(2) . . . . ?
C13 C8 C9 N1 179.34(14) . . . . ?
C7 C8 C9 C10 -179.98(14) . . . . ?
C13 C8 C9 C10 -0.3(2) . . . . ?
N1 C9 C10 C11 -178.62(15) . . . . ?
C8 C9 C10 C11 1.1(2) . . . . ?
C9 C10 C11 C12 -0.8(3) . . . . ?
C10 C11 C12 C13 -0.3(3) . . . . ?
C10 C11 C12 N3 179.37(15) . . . . ?
O1 N3 C12 C13 -175.97(16) . . . . ?
O4 N3 C12 C13 4.9(2) . . . . ?
O1 N3 C12 C11 4.3(2) . . . . ?
O4 N3 C12 C11 -174.82(16) . . . . ?
C11 C12 C13 C8 1.0(2) . . . . ?
N3 C12 C13 C8 -178.65(14) . . . . ?
C7 C8 C13 C12 178.94(15) . . . . ?
C9 C8 C13 C12 -0.7(2) . . . . ?
C2 C3 C15 C16 -2.2(2) . . . . ?
O2 C3 C15 C16 178.65(14) . . . . ?
C2 C3 C15 C6 176.49(15) . . . . ?
O2 C3 C15 C6 -2.7(2) . . . . ?
N1 C6 C15 C3 -175.45(14) . . . . ?
C5 C6 C15 C3 3.8(2) . . . . ?
N1 C6 C15 C16 3.2(2) . . . . ?
C5 C6 C15 C16 -177.55(15) . . . . ?
C3 C15 C16 C17 1.5(2) . . . . ?
C6 C15 C16 C17 -177.15(16) . . . . ?
C15 C16 C17 C1 0.1(3) . . . . ?
C2 C1 C17 C16 -1.0(3) . . . . ?

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
C13 H13 O3 0.93 2.48 3.337(2) 153.0 3_576 yes

_refine_diff_density_max         0.174
_refine_diff_density_min         -0.222
_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_GRK_11
_database_code_depnum_ccdc_archive 'CCDC 2295085'
loop_
_audit_author_name
_audit_author_address
'Dr. Shobhana Krishnaswamy'
;IIT Madras
India
;
_audit_update_record             
;
2023-09-14 deposited with the CCDC.	2025-06-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H18 Cl3 N3 O2'
_chemical_formula_weight         486.76

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   8.815(2)
_cell_length_b                   9.048(3)
_cell_length_c                   14.657(3)
_cell_angle_alpha                77.286(10)
_cell_angle_beta                 85.08(2)
_cell_angle_gamma                75.836(16)
_cell_volume                     1105.1(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    7983
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      27.49

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_F_000             500
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.298
_exptl_crystal_size_mid          0.293
_exptl_crystal_size_min          0.091
_exptl_absorpt_coefficient_mu    0.443
_shelx_estimated_absorpt_T_min   0.879
_shelx_estimated_absorpt_T_max   0.961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6442
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Quest Diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30196
_diffrn_reflns_av_unetI/netI     0.0633
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.372
_diffrn_reflns_theta_max         28.276
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5451
_reflns_number_gt                3129
_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-2019/2 (Sheldrick, 2019), WinGX'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 2012)'
_computing_publication_material  ?
_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)+(0.0564P)²+2.4551P] 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_number_reflns         5451
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1694
_refine_ls_R_factor_gt           0.1006
_refine_ls_wR_factor_ref         0.2250
_refine_ls_wR_factor_gt          0.1907
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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 -0.7589(5) 0.8514(5) -0.2451(3) 0.0589(12) Uani 1 1 d . . . . .
H1A H -0.792771 0.868872 -0.182868 0.071 Uiso 1 1 calc R U . . .
H1B H -0.850874 0.879530 -0.282843 0.071 Uiso 1 1 calc R U . . .
C2 C -0.6506(7) 0.9522(6) -0.2867(4) 0.0796(17) Uani 1 1 d . . . . .
H2A H -0.706786 1.060489 -0.294704 0.095 Uiso 1 1 calc R U . . .
H2B H -0.566857 0.935271 -0.244067 0.095 Uiso 1 1 calc R U . . .
C3 C -0.5821(6) 0.9212(5) -0.3783(3) 0.0596(13) Uani 1 1 d . . . . .
H3A H -0.496539 0.972871 -0.396110 0.072 Uiso 1 1 calc R U . . .
H3B H -0.660927 0.964954 -0.425258 0.072 Uiso 1 1 calc R U . . .
C4 C -0.5219(5) 0.7492(4) -0.3768(3) 0.0400(9) Uani 1 1 d . . . . .
C5 C -0.5768(4) 0.6386(4) -0.3059(2) 0.0357(8) Uani 1 1 d . . . . .
C6 C -0.7430(6) 0.5770(6) -0.1646(3) 0.0616(13) Uani 1 1 d . . . . .
H6A H -0.839033 0.559652 -0.183471 0.074 Uiso 1 1 calc R U . . .
H6B H -0.767148 0.621268 -0.109101 0.074 Uiso 1 1 calc R U . . .
C7 C -0.6264(6) 0.4241(6) -0.1415(3) 0.0590(12) Uani 1 1 d . . . . .
H7A H -0.673527 0.351114 -0.096382 0.071 Uiso 1 1 calc R U . . .
H7B H -0.536996 0.438417 -0.113112 0.071 Uiso 1 1 calc R U . . .
C8 C -0.5718(5) 0.3574(5) -0.2271(3) 0.0470(10) Uani 1 1 d . . . . .
H8A H -0.656864 0.325326 -0.249263 0.056 Uiso 1 1 calc R U . . .
H8B H -0.486465 0.266357 -0.211516 0.056 Uiso 1 1 calc R U . . .
C9 C -0.5177(4) 0.4771(4) -0.3033(2) 0.0358(8) Uani 1 1 d . . . . .
C10 C -0.4066(4) 0.4347(4) -0.3712(2) 0.0330(8) Uani 1 1 d . . . . .
C11 C -0.2366(5) 0.2120(4) -0.4214(3) 0.0408(9) Uani 1 1 d . . . . .
C12 C -0.1731(4) 0.3198(4) -0.4971(2) 0.0341(8) Uani 1 1 d . . . . .
C13 C -0.0575(5) 0.2624(4) -0.5563(3) 0.0393(9) Uani 1 1 d . . . . .
H13 H -0.018655 0.155405 -0.549483 0.047 Uiso 1 1 calc R U . . .
C14 C 0.0027(4) 0.3656(4) -0.6280(2) 0.0350(8) Uani 1 1 d . . . . .
C15 C 0.1184(4) 0.3157(4) -0.6944(3) 0.0391(9) Uani 1 1 d . . . . .
H15 H 0.159587 0.209742 -0.691009 0.047 Uiso 1 1 calc R U . . .
C16 C 0.1707(4) 0.4219(5) -0.7639(3) 0.0382(9) Uani 1 1 d . . . . .
C17 C 0.1115(5) 0.5837(5) -0.7681(3) 0.0438(9) Uani 1 1 d . . . . .
H17 H 0.149018 0.655412 -0.814466 0.053 Uiso 1 1 calc R U . . .
C18 C 0.0006(4) 0.6345(4) -0.7049(3) 0.0397(9) Uani 1 1 d . . . . .
H18 H -0.036419 0.740979 -0.708324 0.048 Uiso 1 1 calc R U . . .
C19 C -0.0602(4) 0.5281(4) -0.6335(2) 0.0333(8) Uani 1 1 d . . . . .
C20 C -0.2297(4) 0.4841(4) -0.5073(2) 0.0311(8) Uani 1 1 d . . . . .
C21 C -0.3503(4) 0.5403(4) -0.4418(2) 0.0326(8) Uani 1 1 d . . . . .
C22 C -0.4119(4) 0.6983(4) -0.4419(3) 0.0380(9) Uani 1 1 d . . . . .
H22 H -0.376790 0.771934 -0.488169 0.046 Uiso 1 1 calc R U . . .
C23 C 0.2838(5) 0.3707(5) -0.8334(3) 0.0476(10) Uani 1 1 d . . . . .
C24 C 0.2437(5) 0.0623(6) -0.9525(3) 0.0622(13) Uani 1 1 d . . . . .
H24 H 0.320366 0.125053 -0.953748 0.075 Uiso 1 1 calc R U . . .
N1 N -0.6855(4) 0.6874(4) -0.2395(2) 0.0464(8) Uani 1 1 d . . . . .
N2 N -0.1738(3) 0.5858(3) -0.5738(2) 0.0339(7) Uani 1 1 d . . . . .
N3 N 0.3719(5) 0.3307(5) -0.8900(3) 0.0669(11) Uani 1 1 d . . . . .
O1 O -0.3517(3) 0.2740(3) -0.36393(17) 0.0401(6) Uani 1 1 d . . . . .
O2 O -0.1935(4) 0.0725(3) -0.4068(2) 0.0662(10) Uani 1 1 d . . . . .
Cl1 Cl 0.0826(2) 0.1799(2) -1.01226(18) 0.1352(9) Uani 1 1 d . . . . .
Cl2 Cl 0.3334(2) -0.0970(2) -1.00283(13) 0.1034(6) Uani 1 1 d . . . . .
Cl3 Cl 0.1914(2) -0.00407(18) -0.83568(11) 0.0966(6) 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 N1 1.453(5) . ?
C1 C2 1.483(7) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.479(7) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.512(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C22 1.371(5) . ?
C4 C5 1.417(5) . ?
C5 N1 1.373(5) . ?
C5 C9 1.419(5) . ?
C6 N1 1.459(5) . ?
C6 C7 1.498(7) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.502(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.509(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.384(5) . ?
C10 C21 1.391(5) . ?
C10 O1 1.399(4) . ?
C11 O2 1.202(4) . ?
C11 O1 1.355(4) . ?
C11 C12 1.476(5) . ?
C12 C13 1.360(5) . ?
C12 C20 1.427(5) . ?
C13 C14 1.404(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.411(5) . ?
C14 C19 1.425(5) . ?
C15 C16 1.371(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.419(5) . ?
C16 C23 1.433(6) . ?
C17 C18 1.355(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.422(5) . ?
C18 H18 0.9300 . ?
C19 N2 1.355(4) . ?
C20 N2 1.336(4) . ?
C20 C21 1.445(5) . ?
C21 C22 1.399(5) . ?
C22 H22 0.9300 . ?
C23 N3 1.143(5) . ?
C24 Cl1 1.726(5) . ?
C24 Cl3 1.748(5) . ?
C24 Cl2 1.748(5) . ?
C24 H24 0.9800 . ?

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
N1 C1 C2 111.8(4) . . ?
N1 C1 H1A 109.3 . . ?
C2 C1 H1A 109.3 . . ?
N1 C1 H1B 109.3 . . ?
C2 C1 H1B 109.3 . . ?
H1A C1 H1B 107.9 . . ?
C3 C2 C1 112.4(5) . . ?
C3 C2 H2A 109.1 . . ?
C1 C2 H2A 109.1 . . ?
C3 C2 H2B 109.1 . . ?
C1 C2 H2B 109.1 . . ?
H2A C2 H2B 107.9 . . ?
C2 C3 C4 112.6(4) . . ?
C2 C3 H3A 109.1 . . ?
C4 C3 H3A 109.1 . . ?
C2 C3 H3B 109.1 . . ?
C4 C3 H3B 109.1 . . ?
H3A C3 H3B 107.8 . . ?
C22 C4 C5 119.4(3) . . ?
C22 C4 C3 120.8(3) . . ?
C5 C4 C3 119.8(3) . . ?
N1 C5 C4 120.1(3) . . ?
N1 C5 C9 120.1(3) . . ?
C4 C5 C9 119.8(3) . . ?
N1 C6 C7 112.2(4) . . ?
N1 C6 H6A 109.2 . . ?
C7 C6 H6A 109.2 . . ?
N1 C6 H6B 109.2 . . ?
C7 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C6 C7 C8 111.6(4) . . ?
C6 C7 H7A 109.3 . . ?
C8 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
C8 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
C7 C8 C9 110.3(3) . . ?
C7 C8 H8A 109.6 . . ?
C9 C8 H8A 109.6 . . ?
C7 C8 H8B 109.6 . . ?
C9 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
C10 C9 C5 117.6(3) . . ?
C10 C9 C8 121.8(3) . . ?
C5 C9 C8 120.6(3) . . ?
C9 C10 C21 124.1(3) . . ?
C9 C10 O1 114.7(3) . . ?
C21 C10 O1 121.2(3) . . ?
O2 C11 O1 117.3(3) . . ?
O2 C11 C12 124.7(4) . . ?
O1 C11 C12 118.0(3) . . ?
C13 C12 C20 119.7(3) . . ?
C13 C12 C11 119.9(3) . . ?
C20 C12 C11 120.4(3) . . ?
C12 C13 C14 119.6(3) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C13 C14 C15 123.2(3) . . ?
C13 C14 C19 117.3(3) . . ?
C15 C14 C19 119.5(3) . . ?
C16 C15 C14 120.6(3) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C17 120.0(3) . . ?
C15 C16 C23 120.5(4) . . ?
C17 C16 C23 119.5(3) . . ?
C18 C17 C16 120.4(4) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C19 121.2(3) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 H18 119.4 . . ?
N2 C19 C18 118.6(3) . . ?
N2 C19 C14 123.3(3) . . ?
C18 C19 C14 118.1(3) . . ?
N2 C20 C12 122.4(3) . . ?
N2 C20 C21 119.7(3) . . ?
C12 C20 C21 117.9(3) . . ?
C10 C21 C22 116.5(3) . . ?
C10 C21 C20 119.9(3) . . ?
C22 C21 C20 123.6(3) . . ?
C4 C22 C21 122.7(3) . . ?
C4 C22 H22 118.6 . . ?
C21 C22 H22 118.6 . . ?
N3 C23 C16 178.7(5) . . ?
Cl1 C24 Cl3 110.4(3) . . ?
Cl1 C24 Cl2 112.8(3) . . ?
Cl3 C24 Cl2 109.4(3) . . ?
Cl1 C24 H24 108.0 . . ?
Cl3 C24 H24 108.0 . . ?
Cl2 C24 H24 108.0 . . ?
C5 N1 C1 121.4(3) . . ?
C5 N1 C6 121.7(3) . . ?
C1 N1 C6 116.7(3) . . ?
C20 N2 C19 117.7(3) . . ?
C11 O1 C10 122.6(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
N1 C1 C2 C3 53.5(6) . . . . ?
C1 C2 C3 C4 -46.7(6) . . . . ?
C2 C3 C4 C22 -158.5(4) . . . . ?
C2 C3 C4 C5 20.0(6) . . . . ?
C22 C4 C5 N1 179.2(4) . . . . ?
C3 C4 C5 N1 0.7(6) . . . . ?
C22 C4 C5 C9 -0.1(6) . . . . ?
C3 C4 C5 C9 -178.5(4) . . . . ?
N1 C6 C7 C8 -53.0(5) . . . . ?
C6 C7 C8 C9 51.5(5) . . . . ?
N1 C5 C9 C10 -179.1(3) . . . . ?
C4 C5 C9 C10 0.2(5) . . . . ?
N1 C5 C9 C8 -0.6(5) . . . . ?
C4 C5 C9 C8 178.6(4) . . . . ?
C7 C8 C9 C10 152.8(4) . . . . ?
C7 C8 C9 C5 -25.5(5) . . . . ?
C5 C9 C10 C21 -0.2(6) . . . . ?
C8 C9 C10 C21 -178.6(4) . . . . ?
C5 C9 C10 O1 179.2(3) . . . . ?
C8 C9 C10 O1 0.8(5) . . . . ?
O2 C11 C12 C13 0.1(6) . . . . ?
O1 C11 C12 C13 -180.0(4) . . . . ?
O2 C11 C12 C20 -178.5(4) . . . . ?
O1 C11 C12 C20 1.4(5) . . . . ?
C20 C12 C13 C14 -1.1(6) . . . . ?
C11 C12 C13 C14 -179.8(3) . . . . ?
C12 C13 C14 C15 -177.6(4) . . . . ?
C12 C13 C14 C19 1.1(5) . . . . ?
C13 C14 C15 C16 178.8(4) . . . . ?
C19 C14 C15 C16 0.0(6) . . . . ?
C14 C15 C16 C17 1.7(6) . . . . ?
C14 C15 C16 C23 -177.6(4) . . . . ?
C15 C16 C17 C18 -1.5(6) . . . . ?
C23 C16 C17 C18 177.8(4) . . . . ?
C16 C17 C18 C19 -0.5(6) . . . . ?
C17 C18 C19 N2 -178.3(4) . . . . ?
C17 C18 C19 C14 2.2(6) . . . . ?
C13 C14 C19 N2 -0.2(5) . . . . ?
C15 C14 C19 N2 178.6(3) . . . . ?
C13 C14 C19 C18 179.3(3) . . . . ?
C15 C14 C19 C18 -1.9(5) . . . . ?
C13 C12 C20 N2 0.3(6) . . . . ?
C11 C12 C20 N2 178.9(3) . . . . ?
C13 C12 C20 C21 -178.8(3) . . . . ?
C11 C12 C20 C21 -0.2(5) . . . . ?
C9 C10 C21 C22 0.1(6) . . . . ?
O1 C10 C21 C22 -179.3(3) . . . . ?
C9 C10 C21 C20 177.6(3) . . . . ?
O1 C10 C21 C20 -1.8(5) . . . . ?
N2 C20 C21 C10 -178.7(3) . . . . ?
C12 C20 C21 C10 0.4(5) . . . . ?
N2 C20 C21 C22 -1.4(5) . . . . ?
C12 C20 C21 C22 177.6(4) . . . . ?
C5 C4 C22 C21 -0.1(6) . . . . ?
C3 C4 C22 C21 178.4(4) . . . . ?
C10 C21 C22 C4 0.0(6) . . . . ?
C20 C21 C22 C4 -177.3(4) . . . . ?
C4 C5 N1 C1 6.4(6) . . . . ?
C9 C5 N1 C1 -174.3(4) . . . . ?
C4 C5 N1 C6 -179.1(4) . . . . ?
C9 C5 N1 C6 0.2(6) . . . . ?
C2 C1 N1 C5 -33.6(6) . . . . ?
C2 C1 N1 C6 151.7(5) . . . . ?
C7 C6 N1 C5 26.9(6) . . . . ?
C7 C6 N1 C1 -158.4(4) . . . . ?
C12 C20 N2 C19 0.6(5) . . . . ?
C21 C20 N2 C19 179.7(3) . . . . ?
C18 C19 N2 C20 179.9(3) . . . . ?
C14 C19 N2 C20 -0.7(5) . . . . ?
O2 C11 O1 C10 177.0(4) . . . . ?
C12 C11 O1 C10 -2.9(5) . . . . ?
C9 C10 O1 C11 -176.3(3) . . . . ?
C21 C10 O1 C11 3.2(5) . . . . ?

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
C7 H7A Cl1 0.97 2.98 3.893(5) 157.3 1_456 yes
C24 H24 N3 0.98 2.41 3.243(7) 142.9 . yes
C7 H7A Cl1 0.97 2.98 3.893(5) 157.3 1_456 yes
C24 H24 N3 0.98 2.41 3.243(7) 142.9 . yes

_refine_diff_density_max         0.685
_refine_diff_density_min         -0.656
_refine_diff_density_rms         0.064

####################################################################### 
# 
# 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 2295078'
loop_
_audit_author_name
_audit_author_address
'Dr. Shobhana Krishnaswamy'
;IIT Madras
India
;
_audit_update_record             
;
2023-09-14 deposited with the CCDC.	2025-06-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H20 N2 O3'
_chemical_formula_weight         372.41

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      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                   19.0707(13)
_cell_length_b                   9.5161(7)
_cell_length_c                   20.4834(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3717.3(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    9886
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      26.26

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_F_000             1568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.136
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6285
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS-2016/2 - Bruker AXS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Quest Diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            47886
_diffrn_reflns_av_unetI/netI     0.0518
_diffrn_reflns_av_R_equivalents  0.0625
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.136
_diffrn_reflns_theta_max         28.277
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             8759
_reflns_number_gt                5327
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.851
_reflns_Friedel_fraction_max     0.899
_reflns_Friedel_fraction_full    0.962

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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-2019/2 (Sheldrick, 2019), WinGX'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 2012)'
_computing_publication_material  ?
_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)+(0.0558P)²+0.3953P] 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 1905 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         8759
_refine_ls_number_parameters     507
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1001
_refine_ls_R_factor_gt           0.0475
_refine_ls_wR_factor_ref         0.1274
_refine_ls_wR_factor_gt          0.1025
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.001

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 0.6137(2) 0.4634(4) 0.3806(2) 0.0706(12) Uani 1 1 d . . . . .
H1A H 0.643484 0.484168 0.417740 0.085 Uiso 1 1 calc R U . . .
H1B H 0.604483 0.550819 0.357800 0.085 Uiso 1 1 calc R U . . .
C2 C 0.6513(2) 0.3635(4) 0.3354(2) 0.0726(12) Uani 1 1 d . . . . .
H2A H 0.694473 0.406272 0.320083 0.087 Uiso 1 1 calc R U . . .
H2B H 0.663217 0.278036 0.358692 0.087 Uiso 1 1 calc R U . . .
C3 C 0.60492(19) 0.3290(4) 0.2781(2) 0.0667(11) Uani 1 1 d . . . . .
H3A H 0.627012 0.256973 0.251588 0.080 Uiso 1 1 calc R U . . .
H3B H 0.598820 0.412032 0.251201 0.080 Uiso 1 1 calc R U . . .
C4 C 0.53364(16) 0.2772(4) 0.30137(18) 0.0480(8) Uani 1 1 d . . . . .
C5 C 0.50748(16) 0.3221(3) 0.36239(17) 0.0437(8) Uani 1 1 d . . . . .
C6 C 0.5151(2) 0.4740(4) 0.4584(2) 0.0591(10) Uani 1 1 d . . . . .
H6A H 0.489394 0.555559 0.443039 0.071 Uiso 1 1 calc R U . . .
H6B H 0.550824 0.506132 0.488605 0.071 Uiso 1 1 calc R U . . .
C7 C 0.46599(19) 0.3765(4) 0.49293(18) 0.0603(10) Uani 1 1 d . . . . .
H7A H 0.443978 0.425558 0.529029 0.072 Uiso 1 1 calc R U . . .
H7B H 0.492193 0.297861 0.510619 0.072 Uiso 1 1 calc R U . . .
C8 C 0.40995(18) 0.3222(4) 0.44694(17) 0.0520(9) Uani 1 1 d . . . . .
H8A H 0.385999 0.243434 0.467074 0.062 Uiso 1 1 calc R U . . .
H8B H 0.375658 0.395664 0.439231 0.062 Uiso 1 1 calc R U . . .
C9 C 0.44076(16) 0.2765(3) 0.38306(16) 0.0418(7) Uani 1 1 d . . . . .
C10 C 0.40429(15) 0.1852(3) 0.34284(15) 0.0388(7) Uani 1 1 d . . . . .
C11 C 0.29718(18) 0.0501(4) 0.33455(17) 0.0471(9) Uani 1 1 d . . . . .
C12 C 0.32387(18) -0.0097(3) 0.27352(18) 0.0407(8) Uani 1 1 d . . . . .
C13 C 0.28477(17) -0.1095(3) 0.24229(16) 0.0462(8) Uani 1 1 d . . . . .
H13 H 0.242694 -0.140256 0.260249 0.055 Uiso 1 1 calc R U . . .
C14 C 0.30862(17) -0.1650(3) 0.18298(16) 0.0449(8) Uani 1 1 d . . . . .
C15 C 0.27051(18) -0.2662(4) 0.14681(17) 0.0511(9) Uani 1 1 d . . . . .
H15 H 0.228047 -0.299901 0.162713 0.061 Uiso 1 1 calc R U . . .
C16 C 0.29573(19) -0.3141(4) 0.08904(18) 0.0540(9) Uani 1 1 d . . . . .
C17 C 0.3603(2) -0.2638(4) 0.06510(19) 0.0630(11) Uani 1 1 d . . . . .
H17 H 0.376950 -0.296405 0.025209 0.076 Uiso 1 1 calc R U . . .
C18 C 0.39851(19) -0.1689(4) 0.09907(17) 0.0572(10) Uani 1 1 d . . . . .
H18 H 0.441499 -0.139011 0.082746 0.069 Uiso 1 1 calc R U . . .
C19 C 0.37375(17) -0.1145(3) 0.15935(16) 0.0436(8) Uani 1 1 d . . . . .
C20 C 0.38872(17) 0.0343(3) 0.24714(16) 0.0383(8) Uani 1 1 d . . . . .
C21 C 0.42952(15) 0.1354(3) 0.28338(15) 0.0376(7) Uani 1 1 d . . . . .
C22 C 0.49521(16) 0.1860(3) 0.26375(17) 0.0443(8) Uani 1 1 d . . . . .
H22 H 0.513406 0.156739 0.223867 0.053 Uiso 1 1 calc R U . . .
C23 C 0.1968(2) -0.4608(4) 0.0707(3) 0.0789(14) Uani 1 1 d . . . . .
H23A H 0.201655 -0.500396 0.113575 0.118 Uiso 1 1 calc R U . . .
H23B H 0.180527 -0.531753 0.041061 0.118 Uiso 1 1 calc R U . . .
H23C H 0.163572 -0.384989 0.072034 0.118 Uiso 1 1 calc R U . . .
C24 C 0.3641(2) 0.0599(4) 0.6179(3) 0.0749(13) Uani 1 1 d . . . . .
H24A H 0.394637 0.042711 0.580866 0.090 Uiso 1 1 calc R U . . .
H24B H 0.353007 -0.030128 0.637544 0.090 Uiso 1 1 calc R U . . .
C25 C 0.4017(2) 0.1483(5) 0.6663(2) 0.0786(13) Uani 1 1 d . . . . .
H25A H 0.417943 0.233698 0.645357 0.094 Uiso 1 1 calc R U . . .
H25B H 0.442344 0.097859 0.682433 0.094 Uiso 1 1 calc R U . . .
C26 C 0.35471(19) 0.1856(5) 0.7226(2) 0.0700(12) Uani 1 1 d . . . . .
H26A H 0.377652 0.255544 0.749692 0.084 Uiso 1 1 calc R U . . .
H26B H 0.346680 0.102746 0.749158 0.084 Uiso 1 1 calc R U . . .
C27 C 0.28544(17) 0.2424(4) 0.69920(19) 0.0511(9) Uani 1 1 d . . . . .
C28 C 0.25948(16) 0.2047(3) 0.63681(17) 0.0466(8) Uani 1 1 d . . . . .
C29 C 0.2691(2) 0.0692(4) 0.5358(2) 0.0708(12) Uani 1 1 d . . . . .
H29A H 0.243442 -0.016028 0.546028 0.085 Uiso 1 1 calc R U . . .
H29B H 0.306132 0.045002 0.505356 0.085 Uiso 1 1 calc R U . . .
C30 C 0.2204(2) 0.1726(5) 0.5042(2) 0.0768(13) Uani 1 1 d . . . . .
H30A H 0.199781 0.130959 0.465510 0.092 Uiso 1 1 calc R U . . .
H30B H 0.246459 0.255386 0.491052 0.092 Uiso 1 1 calc R U . . .
C31 C 0.1634(2) 0.2138(4) 0.55115(18) 0.0623(10) Uani 1 1 d . . . . .
H31A H 0.130953 0.136138 0.556273 0.075 Uiso 1 1 calc R U . . .
H31B H 0.137656 0.293088 0.533550 0.075 Uiso 1 1 calc R U . . .
C32 C 0.19339(17) 0.2528(4) 0.61698(17) 0.0460(8) Uani 1 1 d . . . . .
C33 C 0.15678(16) 0.3409(3) 0.65797(16) 0.0412(7) Uani 1 1 d . . . . .
C34 C 0.0491(2) 0.4727(4) 0.66836(18) 0.0497(9) Uani 1 1 d . . . . .
C35 C 0.07683(18) 0.5333(3) 0.72845(18) 0.0426(8) Uani 1 1 d . . . . .
C36 C 0.03861(17) 0.6345(4) 0.76058(17) 0.0489(9) Uani 1 1 d . . . . .
H36 H -0.004112 0.664387 0.743654 0.059 Uiso 1 1 calc R U . . .
C37 C 0.06398(18) 0.6924(3) 0.81871(17) 0.0474(8) Uani 1 1 d . . . . .
C38 C 0.0268(2) 0.7957(4) 0.85408(19) 0.0565(10) Uani 1 1 d . . . . .
H38 H -0.015628 0.829842 0.838270 0.068 Uiso 1 1 calc R U . . .
C39 C 0.0532(2) 0.8451(4) 0.9114(2) 0.0621(11) Uani 1 1 d . . . . .
C40 C 0.1179(3) 0.7947(4) 0.9348(2) 0.0691(12) Uani 1 1 d . . . . .
H40 H 0.135683 0.829690 0.973776 0.083 Uiso 1 1 calc R U . . .
C41 C 0.1549(2) 0.6956(4) 0.90138(18) 0.0610(10) Uani 1 1 d . . . . .
H41 H 0.197593 0.663985 0.917684 0.073 Uiso 1 1 calc R U . . .
C42 C 0.12881(18) 0.6405(4) 0.84219(16) 0.0471(8) Uani 1 1 d . . . . .
C43 C 0.14178(18) 0.4889(3) 0.75494(17) 0.0396(8) Uani 1 1 d . . . . .
C44 C 0.18192(16) 0.3869(3) 0.71810(15) 0.0415(8) Uani 1 1 d . . . . .
C45 C 0.24681(17) 0.3329(3) 0.73742(18) 0.0475(8) Uani 1 1 d . . . . .
H45 H 0.264696 0.359228 0.777852 0.057 Uiso 1 1 calc R U . . .
C46 C -0.0468(3) 0.9886(5) 0.9304(3) 0.0946(18) Uani 1 1 d . . . . .
H46A H -0.043733 1.031177 0.888028 0.142 Uiso 1 1 calc R U . . .
H46B H -0.064347 1.056045 0.961209 0.142 Uiso 1 1 calc R U . . .
H46C H -0.078018 0.909552 0.928596 0.142 Uiso 1 1 calc R U . . .
N1 N 0.54823(15) 0.4045(3) 0.40336(15) 0.0573(8) Uani 1 1 d . . . . .
N2 N 0.41345(14) -0.0175(3) 0.19118(15) 0.0454(7) Uani 1 1 d . . . . .
N3 N 0.29996(15) 0.1248(3) 0.59505(16) 0.0624(9) Uani 1 1 d . . . . .
N4 N 0.16737(14) 0.5405(3) 0.81077(14) 0.0457(7) Uani 1 1 d . . . . .
O1 O 0.33905(11) 0.1447(2) 0.36644(11) 0.0484(6) Uani 1 1 d . . . . .
O2 O 0.24100(15) 0.0228(3) 0.35846(15) 0.0713(9) Uani 1 1 d . . . . .
O3 O 0.26322(15) -0.4088(3) 0.04909(14) 0.0725(8) Uani 1 1 d . . . . .
O4 O 0.09125(11) 0.3832(2) 0.63491(11) 0.0514(6) Uani 1 1 d . . . . .
O5 O -0.00791(16) 0.4962(3) 0.64587(15) 0.0667(8) Uani 1 1 d . . . . .
O6 O 0.02120(19) 0.9425(3) 0.95041(15) 0.0839(9) 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 N1 1.446(5) . ?
C1 C2 1.508(6) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.507(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.523(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C22 1.373(5) . ?
C4 C5 1.412(5) . ?
C5 N1 1.387(4) . ?
C5 C9 1.409(5) . ?
C6 N1 1.452(5) . ?
C6 C7 1.496(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.515(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.499(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.384(4) . ?
C10 O1 1.390(4) . ?
C10 C21 1.393(4) . ?
C11 O2 1.207(4) . ?
C11 O1 1.369(4) . ?
C11 C12 1.465(5) . ?
C12 C13 1.366(4) . ?
C12 C20 1.413(5) . ?
C13 C14 1.401(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.416(4) . ?
C14 C19 1.417(5) . ?
C15 C16 1.356(5) . ?
C15 H15 0.9300 . ?
C16 O3 1.366(4) . ?
C16 C17 1.409(5) . ?
C17 C18 1.353(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.420(5) . ?
C18 H18 0.9300 . ?
C19 N2 1.361(4) . ?
C20 N2 1.334(4) . ?
C20 C21 1.443(4) . ?
C21 C22 1.401(4) . ?
C22 H22 0.9300 . ?
C23 O3 1.431(5) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 N3 1.447(5) . ?
C24 C25 1.486(6) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C26 1.503(6) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 C27 1.506(5) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 C45 1.377(5) . ?
C27 C28 1.417(5) . ?
C28 N3 1.381(4) . ?
C28 C32 1.401(5) . ?
C29 N3 1.449(5) . ?
C29 C30 1.499(6) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 C31 1.503(5) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 C32 1.511(5) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 C33 1.377(4) . ?
C33 C44 1.392(4) . ?
C33 O4 1.395(4) . ?
C34 O5 1.202(4) . ?
C34 O4 1.357(4) . ?
C34 C35 1.459(5) . ?
C35 C36 1.375(5) . ?
C35 C43 1.417(5) . ?
C36 C37 1.398(5) . ?
C36 H36 0.9300 . ?
C37 C38 1.412(5) . ?
C37 C42 1.415(5) . ?
C38 C39 1.362(6) . ?
C38 H38 0.9300 . ?
C39 O6 1.367(4) . ?
C39 C40 1.406(6) . ?
C40 C41 1.362(5) . ?
C40 H40 0.9300 . ?
C41 C42 1.411(5) . ?
C41 H41 0.9300 . ?
C42 N4 1.364(4) . ?
C43 N4 1.337(4) . ?
C43 C44 1.448(4) . ?
C44 C45 1.397(5) . ?
C45 H45 0.9300 . ?
C46 O6 1.429(6) . ?
C46 H46A 0.9600 . ?
C46 H46B 0.9600 . ?
C46 H46C 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
N1 C1 C2 111.4(3) . . ?
N1 C1 H1A 109.4 . . ?
C2 C1 H1A 109.4 . . ?
N1 C1 H1B 109.4 . . ?
C2 C1 H1B 109.4 . . ?
H1A C1 H1B 108.0 . . ?
C3 C2 C1 109.7(3) . . ?
C3 C2 H2A 109.7 . . ?
C1 C2 H2A 109.7 . . ?
C3 C2 H2B 109.7 . . ?
C1 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
C2 C3 C4 110.5(3) . . ?
C2 C3 H3A 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C22 C4 C5 120.0(3) . . ?
C22 C4 C3 120.3(3) . . ?
C5 C4 C3 119.7(3) . . ?
N1 C5 C9 119.9(3) . . ?
N1 C5 C4 120.6(3) . . ?
C9 C5 C4 119.5(3) . . ?
N1 C6 C7 110.9(3) . . ?
N1 C6 H6A 109.5 . . ?
C7 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 108.0 . . ?
C6 C7 C8 111.0(3) . . ?
C6 C7 H7A 109.4 . . ?
C8 C7 H7A 109.4 . . ?
C6 C7 H7B 109.4 . . ?
C8 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C9 C8 C7 111.4(3) . . ?
C9 C8 H8A 109.3 . . ?
C7 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
C10 C9 C5 117.9(3) . . ?
C10 C9 C8 120.3(3) . . ?
C5 C9 C8 121.8(3) . . ?
C9 C10 O1 114.7(3) . . ?
C9 C10 C21 124.1(3) . . ?
O1 C10 C21 121.2(3) . . ?
O2 C11 O1 117.8(3) . . ?
O2 C11 C12 124.8(3) . . ?
O1 C11 C12 117.4(3) . . ?
C13 C12 C20 120.3(3) . . ?
C13 C12 C11 118.7(3) . . ?
C20 C12 C11 121.0(3) . . ?
C12 C13 C14 119.4(3) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C13 C14 C15 122.9(3) . . ?
C13 C14 C19 117.0(3) . . ?
C15 C14 C19 120.1(3) . . ?
C16 C15 C14 120.2(3) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 O3 125.7(4) . . ?
C15 C16 C17 120.0(3) . . ?
O3 C16 C17 114.3(3) . . ?
C18 C17 C16 121.2(3) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C17 C18 C19 120.8(3) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
N2 C19 C14 123.6(3) . . ?
N2 C19 C18 118.6(3) . . ?
C14 C19 C18 117.7(3) . . ?
N2 C20 C12 121.9(3) . . ?
N2 C20 C21 119.8(3) . . ?
C12 C20 C21 118.2(3) . . ?
C10 C21 C22 116.3(3) . . ?
C10 C21 C20 119.4(3) . . ?
C22 C21 C20 124.3(3) . . ?
C4 C22 C21 122.2(3) . . ?
C4 C22 H22 118.9 . . ?
C21 C22 H22 118.9 . . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O3 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N3 C24 C25 112.4(3) . . ?
N3 C24 H24A 109.1 . . ?
C25 C24 H24A 109.1 . . ?
N3 C24 H24B 109.1 . . ?
C25 C24 H24B 109.1 . . ?
H24A C24 H24B 107.8 . . ?
C24 C25 C26 111.0(4) . . ?
C24 C25 H25A 109.4 . . ?
C26 C25 H25A 109.4 . . ?
C24 C25 H25B 109.4 . . ?
C26 C25 H25B 109.4 . . ?
H25A C25 H25B 108.0 . . ?
C25 C26 C27 111.3(4) . . ?
C25 C26 H26A 109.4 . . ?
C27 C26 H26A 109.4 . . ?
C25 C26 H26B 109.4 . . ?
C27 C26 H26B 109.4 . . ?
H26A C26 H26B 108.0 . . ?
C45 C27 C28 119.0(3) . . ?
C45 C27 C26 120.8(4) . . ?
C28 C27 C26 120.2(3) . . ?
N3 C28 C32 120.2(3) . . ?
N3 C28 C27 120.2(3) . . ?
C32 C28 C27 119.6(3) . . ?
N3 C29 C30 111.9(3) . . ?
N3 C29 H29A 109.2 . . ?
C30 C29 H29A 109.2 . . ?
N3 C29 H29B 109.2 . . ?
C30 C29 H29B 109.2 . . ?
H29A C29 H29B 107.9 . . ?
C29 C30 C31 110.1(4) . . ?
C29 C30 H30A 109.6 . . ?
C31 C30 H30A 109.6 . . ?
C29 C30 H30B 109.6 . . ?
C31 C30 H30B 109.6 . . ?
H30A C30 H30B 108.2 . . ?
C30 C31 C32 111.2(3) . . ?
C30 C31 H31A 109.4 . . ?
C32 C31 H31A 109.4 . . ?
C30 C31 H31B 109.4 . . ?
C32 C31 H31B 109.4 . . ?
H31A C31 H31B 108.0 . . ?
C33 C32 C28 118.6(3) . . ?
C33 C32 C31 120.1(3) . . ?
C28 C32 C31 121.2(3) . . ?
C32 C33 C44 123.8(3) . . ?
C32 C33 O4 115.0(3) . . ?
C44 C33 O4 121.2(3) . . ?
O5 C34 O4 117.3(3) . . ?
O5 C34 C35 125.3(3) . . ?
O4 C34 C35 117.4(3) . . ?
C36 C35 C43 119.3(3) . . ?
C36 C35 C34 119.3(3) . . ?
C43 C35 C34 121.5(3) . . ?
C35 C36 C37 120.0(3) . . ?
C35 C36 H36 120.0 . . ?
C37 C36 H36 120.0 . . ?
C36 C37 C38 122.5(3) . . ?
C36 C37 C42 117.0(3) . . ?
C38 C37 C42 120.5(3) . . ?
C39 C38 C37 119.8(4) . . ?
C39 C38 H38 120.1 . . ?
C37 C38 H38 120.1 . . ?
C38 C39 O6 124.9(4) . . ?
C38 C39 C40 120.0(4) . . ?
O6 C39 C40 115.1(4) . . ?
C41 C40 C39 121.3(4) . . ?
C41 C40 H40 119.3 . . ?
C39 C40 H40 119.3 . . ?
C40 C41 C42 120.4(4) . . ?
C40 C41 H41 119.8 . . ?
C42 C41 H41 119.8 . . ?
N4 C42 C41 118.3(3) . . ?
N4 C42 C37 123.6(3) . . ?
C41 C42 C37 118.1(3) . . ?
N4 C43 C35 122.5(3) . . ?
N4 C43 C44 119.9(3) . . ?
C35 C43 C44 117.6(3) . . ?
C33 C44 C45 116.1(3) . . ?
C33 C44 C43 119.3(3) . . ?
C45 C44 C43 124.5(3) . . ?
C27 C45 C44 122.9(3) . . ?
C27 C45 H45 118.6 . . ?
C44 C45 H45 118.6 . . ?
O6 C46 H46A 109.5 . . ?
O6 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
O6 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C5 N1 C1 120.5(3) . . ?
C5 N1 C6 118.9(3) . . ?
C1 N1 C6 116.7(3) . . ?
C20 N2 C19 117.8(3) . . ?
C28 N3 C24 120.5(3) . . ?
C28 N3 C29 119.5(3) . . ?
C24 N3 C29 117.3(3) . . ?
C43 N4 C42 117.6(3) . . ?
C11 O1 C10 122.6(3) . . ?
C16 O3 C23 116.4(3) . . ?
C34 O4 C33 122.7(3) . . ?
C39 O6 C46 116.5(4) . . ?

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
N1 C1 C2 C3 58.1(5) . . . . ?
C1 C2 C3 C4 -53.0(5) . . . . ?
C2 C3 C4 C22 -151.7(3) . . . . ?
C2 C3 C4 C5 27.5(5) . . . . ?
C22 C4 C5 N1 174.4(3) . . . . ?
C3 C4 C5 N1 -4.8(5) . . . . ?
C22 C4 C5 C9 -2.3(5) . . . . ?
C3 C4 C5 C9 178.5(3) . . . . ?
N1 C6 C7 C8 -58.3(4) . . . . ?
C6 C7 C8 C9 45.5(4) . . . . ?
N1 C5 C9 C10 -174.9(3) . . . . ?
C4 C5 C9 C10 1.9(4) . . . . ?
N1 C5 C9 C8 4.0(5) . . . . ?
C4 C5 C9 C8 -179.2(3) . . . . ?
C7 C8 C9 C10 159.7(3) . . . . ?
C7 C8 C9 C5 -19.2(5) . . . . ?
C5 C9 C10 O1 179.9(3) . . . . ?
C8 C9 C10 O1 0.9(4) . . . . ?
C5 C9 C10 C21 0.2(5) . . . . ?
C8 C9 C10 C21 -178.7(3) . . . . ?
O2 C11 C12 C13 -3.6(6) . . . . ?
O1 C11 C12 C13 176.8(3) . . . . ?
O2 C11 C12 C20 176.4(4) . . . . ?
O1 C11 C12 C20 -3.2(5) . . . . ?
C20 C12 C13 C14 -1.7(5) . . . . ?
C11 C12 C13 C14 178.3(3) . . . . ?
C12 C13 C14 C15 -178.5(3) . . . . ?
C12 C13 C14 C19 1.1(5) . . . . ?
C13 C14 C15 C16 178.8(3) . . . . ?
C19 C14 C15 C16 -0.8(5) . . . . ?
C14 C15 C16 O3 -178.4(3) . . . . ?
C14 C15 C16 C17 0.4(5) . . . . ?
C15 C16 C17 C18 0.7(6) . . . . ?
O3 C16 C17 C18 179.7(3) . . . . ?
C16 C17 C18 C19 -1.5(6) . . . . ?
C13 C14 C19 N2 0.4(5) . . . . ?
C15 C14 C19 N2 -180.0(3) . . . . ?
C13 C14 C19 C18 -179.6(3) . . . . ?
C15 C14 C19 C18 0.0(5) . . . . ?
C17 C18 C19 N2 -178.9(3) . . . . ?
C17 C18 C19 C14 1.2(5) . . . . ?
C13 C12 C20 N2 0.9(5) . . . . ?
C11 C12 C20 N2 -179.1(3) . . . . ?
C13 C12 C20 C21 -177.3(3) . . . . ?
C11 C12 C20 C21 2.7(5) . . . . ?
C9 C10 C21 C22 -1.8(5) . . . . ?
O1 C10 C21 C22 178.5(3) . . . . ?
C9 C10 C21 C20 176.5(3) . . . . ?
O1 C10 C21 C20 -3.1(4) . . . . ?
N2 C20 C21 C10 -177.9(3) . . . . ?
C12 C20 C21 C10 0.5(4) . . . . ?
N2 C20 C21 C22 0.3(5) . . . . ?
C12 C20 C21 C22 178.7(3) . . . . ?
C5 C4 C22 C21 0.6(5) . . . . ?
C3 C4 C22 C21 179.8(3) . . . . ?
C10 C21 C22 C4 1.4(5) . . . . ?
C20 C21 C22 C4 -176.9(3) . . . . ?
N3 C24 C25 C26 55.1(5) . . . . ?
C24 C25 C26 C27 -49.6(5) . . . . ?
C25 C26 C27 C45 -153.6(4) . . . . ?
C25 C26 C27 C28 25.5(5) . . . . ?
C45 C27 C28 N3 174.0(3) . . . . ?
C26 C27 C28 N3 -5.1(5) . . . . ?
C45 C27 C28 C32 -4.0(5) . . . . ?
C26 C27 C28 C32 176.9(3) . . . . ?
N3 C29 C30 C31 -57.7(5) . . . . ?
C29 C30 C31 C32 48.4(5) . . . . ?
N3 C28 C32 C33 -175.2(3) . . . . ?
C27 C28 C32 C33 2.8(5) . . . . ?
N3 C28 C32 C31 2.7(5) . . . . ?
C27 C28 C32 C31 -179.3(3) . . . . ?
C30 C31 C32 C33 155.6(4) . . . . ?
C30 C31 C32 C28 -22.2(5) . . . . ?
C28 C32 C33 C44 0.8(5) . . . . ?
C31 C32 C33 C44 -177.1(3) . . . . ?
C28 C32 C33 O4 -179.5(3) . . . . ?
C31 C32 C33 O4 2.6(5) . . . . ?
O5 C34 C35 C36 -5.6(6) . . . . ?
O4 C34 C35 C36 173.9(3) . . . . ?
O5 C34 C35 C43 173.5(4) . . . . ?
O4 C34 C35 C43 -7.0(5) . . . . ?
C43 C35 C36 C37 0.0(5) . . . . ?
C34 C35 C36 C37 179.2(3) . . . . ?
C35 C36 C37 C38 -179.5(3) . . . . ?
C35 C36 C37 C42 -0.9(5) . . . . ?
C36 C37 C38 C39 178.1(3) . . . . ?
C42 C37 C38 C39 -0.4(5) . . . . ?
C37 C38 C39 O6 -178.5(3) . . . . ?
C37 C38 C39 C40 0.9(5) . . . . ?
C38 C39 C40 C41 -0.6(6) . . . . ?
O6 C39 C40 C41 178.9(3) . . . . ?
C39 C40 C41 C42 -0.2(6) . . . . ?
C40 C41 C42 N4 -179.4(3) . . . . ?
C40 C41 C42 C37 0.6(5) . . . . ?
C36 C37 C42 N4 1.1(5) . . . . ?
C38 C37 C42 N4 179.7(3) . . . . ?
C36 C37 C42 C41 -178.9(3) . . . . ?
C38 C37 C42 C41 -0.3(5) . . . . ?
C36 C35 C43 N4 0.8(5) . . . . ?
C34 C35 C43 N4 -178.3(3) . . . . ?
C36 C35 C43 C44 -177.2(3) . . . . ?
C34 C35 C43 C44 3.7(5) . . . . ?
C32 C33 C44 C45 -3.0(5) . . . . ?
O4 C33 C44 C45 177.3(3) . . . . ?
C32 C33 C44 C43 174.8(3) . . . . ?
O4 C33 C44 C43 -4.9(5) . . . . ?
N4 C43 C44 C33 -175.9(3) . . . . ?
C35 C43 C44 C33 2.2(4) . . . . ?
N4 C43 C44 C45 1.8(5) . . . . ?
C35 C43 C44 C45 179.9(3) . . . . ?
C28 C27 C45 C44 1.7(5) . . . . ?
C26 C27 C45 C44 -179.2(3) . . . . ?
C33 C44 C45 C27 1.7(5) . . . . ?
C43 C44 C45 C27 -176.0(3) . . . . ?
C9 C5 N1 C1 -173.9(3) . . . . ?
C4 C5 N1 C1 9.3(5) . . . . ?
C9 C5 N1 C6 -16.7(4) . . . . ?
C4 C5 N1 C6 166.5(3) . . . . ?
C2 C1 N1 C5 -36.3(5) . . . . ?
C2 C1 N1 C6 166.0(3) . . . . ?
C7 C6 N1 C5 44.1(4) . . . . ?
C7 C6 N1 C1 -157.9(3) . . . . ?
C12 C20 N2 C19 0.5(5) . . . . ?
C21 C20 N2 C19 178.8(3) . . . . ?
C14 C19 N2 C20 -1.2(5) . . . . ?
C18 C19 N2 C20 178.8(3) . . . . ?
C32 C28 N3 C24 -172.1(3) . . . . ?
C27 C28 N3 C24 9.9(5) . . . . ?
C32 C28 N3 C29 -11.3(5) . . . . ?
C27 C28 N3 C29 170.7(3) . . . . ?
C25 C24 N3 C28 -35.3(5) . . . . ?
C25 C24 N3 C29 163.5(4) . . . . ?
C30 C29 N3 C28 39.3(5) . . . . ?
C30 C29 N3 C24 -159.3(3) . . . . ?
C35 C43 N4 C42 -0.6(5) . . . . ?
C44 C43 N4 C42 177.3(3) . . . . ?
C41 C42 N4 C43 179.7(3) . . . . ?
C37 C42 N4 C43 -0.3(5) . . . . ?
O2 C11 O1 C10 -179.1(3) . . . . ?
C12 C11 O1 C10 0.5(5) . . . . ?
C9 C10 O1 C11 -177.0(3) . . . . ?
C21 C10 O1 C11 2.7(5) . . . . ?
C15 C16 O3 C23 0.1(5) . . . . ?
C17 C16 O3 C23 -178.8(3) . . . . ?
O5 C34 O4 C33 -176.0(3) . . . . ?
C35 C34 O4 C33 4.4(5) . . . . ?
C32 C33 O4 C34 -178.3(3) . . . . ?
C44 C33 O4 C34 1.5(5) . . . . ?
C38 C39 O6 C46 3.6(5) . . . . ?
C40 C39 O6 C46 -175.8(4) . . . . ?

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 H2A N4 0.97 2.69 3.612(5) 158.9 2_664 yes
C30 H30A O2 0.97 2.55 3.332(5) 138.1 . yes
C2 H2A N4 0.97 2.69 3.612(5) 158.9 2_664 yes
C30 H30A O2 0.97 2.55 3.332(5) 138.1 . yes

_refine_diff_density_max         0.173
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.034



