# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_ARDRDMCL_0m
_database_code_depnum_ccdc_archive 'CCDC 2103980'
loop_
_audit_author_name
_audit_author_address
'RIYA BAG'
;UNIVERSITY OF CALCUTTA
India
;
_audit_update_record             
;
2021-08-18 deposited with the CCDC.	2022-03-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H22 Cl2 N4 O5'
_chemical_formula_sum            'C36 H22 Cl2 N4 O5'
_chemical_formula_weight         661.47

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                   8.346(4)
_cell_length_b                   12.269(6)
_cell_length_c                   14.899(7)
_cell_angle_alpha                92.200(7)
_cell_angle_beta                 101.408(7)
_cell_angle_gamma                92.387(7)
_cell_volume                     1492.5(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    5760
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      28.24

_exptl_crystal_description       square
_exptl_crystal_colour            White
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.54
_exptl_crystal_size_min          0.48
_exptl_absorpt_coefficient_mu    0.271
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4562
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(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            30198
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.396
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_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             5261
_reflns_number_gt                4292
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_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)+(0.1000P)²+0.9785P] 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         5261
_refine_ls_number_parameters     424
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.1600
_refine_ls_wR_factor_gt          0.1278
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_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
Cl1 Cl 0.97854(9) 0.16981(5) 1.01851(5) 0.0565(2) Uani 1 1 d . . . . .
Cl2 Cl 0.85583(11) 0.47734(6) 0.77385(5) 0.0604(3) Uani 1 1 d . . . . .
O1 O 0.50403(19) 0.72200(12) 0.83423(11) 0.0359(4) Uani 1 1 d . . . . .
O2 O 0.46958(19) 0.53757(12) 0.80069(10) 0.0343(4) Uani 1 1 d . . . . .
O3 O 0.6896(3) 0.66392(15) 0.98597(13) 0.0554(5) Uani 1 1 d . . . . .
O4 O 0.2216(3) 0.48210(18) 0.44017(14) 0.0737(7) Uani 1 1 d . . . . .
O5 O 0.8464(2) 1.08982(14) 0.79322(13) 0.0497(5) Uani 1 1 d . . . . .
N1 N 0.7938(2) 0.90591(14) 0.76713(14) 0.0341(4) Uani 1 1 d . . . . .
N2 N 0.7114(2) 0.81007(14) 0.78282(14) 0.0346(4) Uani 1 1 d . . . . .
N3 N 0.4401(2) 0.59589(15) 0.65505(13) 0.0345(4) Uani 1 1 d . . . . .
N4 N 0.3744(2) 0.58322(16) 0.56229(13) 0.0363(4) Uani 1 1 d . . . . .
C1 C 1.1816(4) 0.8470(3) 0.6318(3) 0.0722(10) Uani 1 1 d . . . . .
H1 H 1.268548 0.834097 0.602828 0.087 Uiso 1 1 calc R U . . .
C2 C 1.1083(4) 0.9448(3) 0.6244(3) 0.0762(11) Uani 1 1 d . . . . .
H3 H 1.145108 0.997905 0.589277 0.091 Uiso 1 1 calc R U . . .
C3 C 0.9802(4) 0.9664(2) 0.6681(2) 0.0609(8) Uani 1 1 d . . . . .
H4 H 0.930437 1.032873 0.661847 0.073 Uiso 1 1 calc R U . . .
C4 C 0.9273(3) 0.8874(2) 0.72129(17) 0.0382(5) Uani 1 1 d . . . . .
C5 C 0.5854(3) 0.81651(17) 0.81826(15) 0.0299(5) Uani 1 1 d . . . . .
C6 C 0.5873(3) 0.62465(16) 0.82696(16) 0.0324(5) Uani 1 1 d . . . . .
H12 H 0.660306 0.630925 0.783162 0.039 Uiso 1 1 calc R U . . .
C7 C 0.4045(3) 0.52326(17) 0.70832(15) 0.0307(5) Uani 1 1 d . . . . .
C8 C 0.4220(3) 0.6728(2) 0.51166(17) 0.0399(5) Uani 1 1 d . . . . .
C9 C 0.3329(4) 0.6950(3) 0.4265(2) 0.0594(8) Uani 1 1 d . . . . .
H14 H 0.243176 0.649561 0.399072 0.071 Uiso 1 1 calc R U . . .
C10 C 0.3774(5) 0.7850(3) 0.3821(2) 0.0779(10) Uani 1 1 d . . . . .
H15 H 0.317829 0.798678 0.324283 0.094 Uiso 1 1 calc R U . . .
C11 C 0.5064(5) 0.8538(3) 0.4210(3) 0.0743(10) Uani 1 1 d . . . . .
H2 H 0.534371 0.914524 0.390800 0.089 Uiso 1 1 calc R U . . .
C12 C 0.7576(3) 1.00828(18) 0.79789(16) 0.0344(5) Uani 1 1 d . . . . .
C13 C 0.6075(3) 1.01201(17) 0.83439(15) 0.0332(5) Uani 1 1 d . . . . .
C14 C 0.5525(3) 1.11262(19) 0.85949(18) 0.0432(6) Uani 1 1 d . . . . .
H5 H 0.611597 1.176929 0.853389 0.052 Uiso 1 1 calc R U . . .
C15 C 0.4112(4) 1.1163(2) 0.8931(2) 0.0506(7) Uani 1 1 d . . . . .
H6 H 0.375634 1.183369 0.910241 0.061 Uiso 1 1 calc R U . . .
C16 C 0.3208(3) 1.0214(2) 0.9019(2) 0.0516(7) Uani 1 1 d . . . . .
H7 H 0.223920 1.025306 0.923555 0.062 Uiso 1 1 calc R U . . .
C17 C 0.3739(3) 0.9214(2) 0.87868(18) 0.0419(6) Uani 1 1 d . . . . .
H8 H 0.314266 0.857608 0.885558 0.050 Uiso 1 1 calc R U . . .
C18 C 0.5178(3) 0.91633(17) 0.84478(15) 0.0318(5) Uani 1 1 d . . . . .
C19 C 0.6823(3) 0.59882(18) 0.92255(16) 0.0342(5) Uani 1 1 d . . . . .
C20 C 0.7582(3) 0.49051(18) 0.93902(15) 0.0321(5) Uani 1 1 d . . . . .
C21 C 0.8346(3) 0.43072(19) 0.87961(15) 0.0352(5) Uani 1 1 d . . . . .
C22 C 0.9033(3) 0.33244(19) 0.90368(16) 0.0385(5) Uani 1 1 d . . . . .
H9 H 0.954443 0.293508 0.863524 0.046 Uiso 1 1 calc R U . . .
C23 C 0.8943(3) 0.29319(19) 0.98855(17) 0.0383(5) Uani 1 1 d . . . . .
C24 C 0.8201(3) 0.3497(2) 1.04931(17) 0.0443(6) Uani 1 1 d . . . . .
H10 H 0.814538 0.322427 1.106075 0.053 Uiso 1 1 calc R U . . .
C25 C 0.7538(3) 0.4480(2) 1.02384(16) 0.0414(6) Uani 1 1 d . . . . .
H11 H 0.704601 0.487115 1.064828 0.050 Uiso 1 1 calc R U . . .
C26 C 0.5541(4) 0.7417(2) 0.5513(2) 0.0551(7) Uani 1 1 d . . . . .
H13 H 0.616002 0.727544 0.608370 0.066 Uiso 1 1 calc R U . . .
C27 C 0.5941(4) 0.8322(3) 0.5056(2) 0.0696(9) Uani 1 1 d . . . . .
H16 H 0.682202 0.878992 0.532927 0.084 Uiso 1 1 calc R U . . .
C28 C 0.2710(3) 0.4946(2) 0.52287(18) 0.0448(6) Uani 1 1 d . . . . .
C29 C 0.2289(3) 0.41635(19) 0.58809(17) 0.0402(5) Uani 1 1 d . . . . .
C30 C 0.1196(4) 0.3277(2) 0.5552(2) 0.0568(7) Uani 1 1 d . . . . .
H17 H 0.072734 0.319606 0.493121 0.068 Uiso 1 1 calc R U . . .
C31 C 0.0818(4) 0.2531(2) 0.6145(2) 0.0595(8) Uani 1 1 d . . . . .
H18 H 0.008496 0.194476 0.592478 0.071 Uiso 1 1 calc R U . . .
C32 C 0.1516(4) 0.2636(2) 0.7073(2) 0.0520(7) Uani 1 1 d . . . . .
H19 H 0.125585 0.211633 0.746597 0.062 Uiso 1 1 calc R U . . .
C33 C 0.2592(3) 0.35068(19) 0.74165(18) 0.0425(6) Uani 1 1 d . . . . .
H20 H 0.305939 0.357712 0.803782 0.051 Uiso 1 1 calc R U . . .
C34 C 0.2968(3) 0.42842(18) 0.68125(16) 0.0343(5) Uani 1 1 d . . . . .
C35 C 0.9978(3) 0.7875(2) 0.72670(19) 0.0474(6) Uani 1 1 d . . . . .
H21 H 0.959761 0.733082 0.760087 0.057 Uiso 1 1 calc R U . . .
C36 C 1.1257(4) 0.7688(3) 0.6820(2) 0.0642(8) Uani 1 1 d . . . . .
H22 H 1.174122 0.701789 0.686521 0.077 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
Cl1 C23 1.732(3) . ?
Cl2 C21 1.736(2) . ?
O1 C5 1.372(3) . ?
O1 C6 1.418(3) . ?
O2 C7 1.378(3) . ?
O2 C6 1.410(3) . ?
O3 C19 1.204(3) . ?
O4 C28 1.221(3) . ?
O5 C12 1.232(3) . ?
N1 C12 1.386(3) . ?
N1 N2 1.389(3) . ?
N1 C4 1.438(3) . ?
N2 C5 1.270(3) . ?
N3 C7 1.280(3) . ?
N3 N4 1.383(3) . ?
N4 C28 1.394(3) . ?
N4 C8 1.442(3) . ?
C1 C36 1.362(5) . ?
C1 C2 1.368(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.388(4) . ?
C2 H3 0.9300 . ?
C3 C4 1.387(4) . ?
C3 H4 0.9300 . ?
C4 C35 1.379(4) . ?
C5 C18 1.443(3) . ?
C6 C19 1.538(3) . ?
C6 H12 0.9800 . ?
C7 C34 1.434(3) . ?
C8 C26 1.380(4) . ?
C8 C9 1.381(4) . ?
C9 C10 1.384(4) . ?
C9 H14 0.9300 . ?
C10 C11 1.360(5) . ?
C10 H15 0.9300 . ?
C11 C27 1.367(5) . ?
C11 H2 0.9300 . ?
C12 C13 1.462(3) . ?
C13 C18 1.396(3) . ?
C13 C14 1.398(3) . ?
C14 C15 1.371(4) . ?
C14 H5 0.9300 . ?
C15 C16 1.386(4) . ?
C15 H6 0.9300 . ?
C16 C17 1.377(4) . ?
C16 H7 0.9300 . ?
C17 C18 1.394(3) . ?
C17 H8 0.9300 . ?
C19 C20 1.504(3) . ?
C20 C25 1.392(3) . ?
C20 C21 1.393(3) . ?
C21 C22 1.386(3) . ?
C22 C23 1.385(3) . ?
C22 H9 0.9300 . ?
C23 C24 1.376(4) . ?
C24 C25 1.383(4) . ?
C24 H10 0.9300 . ?
C25 H11 0.9300 . ?
C26 C27 1.388(4) . ?
C26 H13 0.9300 . ?
C27 H16 0.9300 . ?
C28 C29 1.473(4) . ?
C29 C34 1.391(4) . ?
C29 C30 1.398(4) . ?
C30 C31 1.367(4) . ?
C30 H17 0.9300 . ?
C31 C32 1.388(4) . ?
C31 H18 0.9300 . ?
C32 C33 1.380(4) . ?
C32 H19 0.9300 . ?
C33 C34 1.404(3) . ?
C33 H20 0.9300 . ?
C35 C36 1.388(4) . ?
C35 H21 0.9300 . ?
C36 H22 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
C5 O1 C6 115.78(16) . . ?
C7 O2 C6 116.29(16) . . ?
C12 N1 N2 123.22(19) . . ?
C12 N1 C4 123.54(19) . . ?
N2 N1 C4 113.12(17) . . ?
C5 N2 N1 118.75(18) . . ?
C7 N3 N4 118.89(19) . . ?
N3 N4 C28 123.47(19) . . ?
N3 N4 C8 112.46(19) . . ?
C28 N4 C8 124.1(2) . . ?
C36 C1 C2 119.1(3) . . ?
C36 C1 H1 120.4 . . ?
C2 C1 H1 120.4 . . ?
C1 C2 C3 121.4(3) . . ?
C1 C2 H3 119.3 . . ?
C3 C2 H3 119.3 . . ?
C4 C3 C2 119.0(3) . . ?
C4 C3 H4 120.5 . . ?
C2 C3 H4 120.5 . . ?
C35 C4 C3 119.7(2) . . ?
C35 C4 N1 119.3(2) . . ?
C3 C4 N1 120.9(2) . . ?
N2 C5 O1 118.92(19) . . ?
N2 C5 C18 125.7(2) . . ?
O1 C5 C18 115.40(19) . . ?
O2 C6 O1 108.32(18) . . ?
O2 C6 C19 105.62(17) . . ?
O1 C6 C19 108.97(18) . . ?
O2 C6 H12 111.2 . . ?
O1 C6 H12 111.2 . . ?
C19 C6 H12 111.2 . . ?
N3 C7 O2 118.22(19) . . ?
N3 C7 C34 125.9(2) . . ?
O2 C7 C34 115.88(19) . . ?
C26 C8 C9 119.1(2) . . ?
C26 C8 N4 119.3(2) . . ?
C9 C8 N4 121.5(2) . . ?
C8 C9 C10 119.8(3) . . ?
C8 C9 H14 120.1 . . ?
C10 C9 H14 120.1 . . ?
C11 C10 C9 121.4(3) . . ?
C11 C10 H15 119.3 . . ?
C9 C10 H15 119.3 . . ?
C10 C11 C27 118.8(3) . . ?
C10 C11 H2 120.6 . . ?
C27 C11 H2 120.6 . . ?
O5 C12 N1 121.3(2) . . ?
O5 C12 C13 123.2(2) . . ?
N1 C12 C13 115.44(19) . . ?
C18 C13 C14 119.2(2) . . ?
C18 C13 C12 121.0(2) . . ?
C14 C13 C12 119.8(2) . . ?
C15 C14 C13 119.9(2) . . ?
C15 C14 H5 120.1 . . ?
C13 C14 H5 120.1 . . ?
C14 C15 C16 120.9(2) . . ?
C14 C15 H6 119.6 . . ?
C16 C15 H6 119.6 . . ?
C17 C16 C15 120.2(2) . . ?
C17 C16 H7 119.9 . . ?
C15 C16 H7 119.9 . . ?
C16 C17 C18 119.6(2) . . ?
C16 C17 H8 120.2 . . ?
C18 C17 H8 120.2 . . ?
C17 C18 C13 120.3(2) . . ?
C17 C18 C5 124.6(2) . . ?
C13 C18 C5 115.2(2) . . ?
O3 C19 C20 119.4(2) . . ?
O3 C19 C6 119.7(2) . . ?
C20 C19 C6 120.78(18) . . ?
C25 C20 C21 117.5(2) . . ?
C25 C20 C19 115.59(19) . . ?
C21 C20 C19 126.9(2) . . ?
C22 C21 C20 121.4(2) . . ?
C22 C21 Cl2 116.50(17) . . ?
C20 C21 Cl2 122.05(18) . . ?
C23 C22 C21 118.9(2) . . ?
C23 C22 H9 120.6 . . ?
C21 C22 H9 120.6 . . ?
C24 C23 C22 121.6(2) . . ?
C24 C23 Cl1 119.41(19) . . ?
C22 C23 Cl1 119.00(19) . . ?
C23 C24 C25 118.3(2) . . ?
C23 C24 H10 120.8 . . ?
C25 C24 H10 120.8 . . ?
C24 C25 C20 122.3(2) . . ?
C24 C25 H11 118.8 . . ?
C20 C25 H11 118.8 . . ?
C8 C26 C27 119.7(3) . . ?
C8 C26 H13 120.2 . . ?
C27 C26 H13 120.2 . . ?
C11 C27 C26 121.2(3) . . ?
C11 C27 H16 119.4 . . ?
C26 C27 H16 119.4 . . ?
O4 C28 N4 122.3(2) . . ?
O4 C28 C29 122.6(2) . . ?
N4 C28 C29 115.1(2) . . ?
C34 C29 C30 119.6(2) . . ?
C34 C29 C28 121.3(2) . . ?
C30 C29 C28 119.1(2) . . ?
C31 C30 C29 119.8(3) . . ?
C31 C30 H17 120.1 . . ?
C29 C30 H17 120.1 . . ?
C30 C31 C32 120.8(3) . . ?
C30 C31 H18 119.6 . . ?
C32 C31 H18 119.6 . . ?
C33 C32 C31 120.6(3) . . ?
C33 C32 H19 119.7 . . ?
C31 C32 H19 119.7 . . ?
C32 C33 C34 118.9(3) . . ?
C32 C33 H20 120.6 . . ?
C34 C33 H20 120.6 . . ?
C29 C34 C33 120.3(2) . . ?
C29 C34 C7 115.3(2) . . ?
C33 C34 C7 124.4(2) . . ?
C4 C35 C36 119.6(3) . . ?
C4 C35 H21 120.2 . . ?
C36 C35 H21 120.2 . . ?
C1 C36 C35 121.1(3) . . ?
C1 C36 H22 119.5 . . ?
C35 C36 H22 119.5 . . ?

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
C12 N1 N2 C5 7.9(3) . . . . ?
C4 N1 N2 C5 -176.1(2) . . . . ?
C7 N3 N4 C28 -0.4(3) . . . . ?
C7 N3 N4 C8 178.44(19) . . . . ?
C36 C1 C2 C3 1.0(6) . . . . ?
C1 C2 C3 C4 0.8(6) . . . . ?
C2 C3 C4 C35 -2.7(5) . . . . ?
C2 C3 C4 N1 -179.4(3) . . . . ?
C12 N1 C4 C35 153.1(2) . . . . ?
N2 N1 C4 C35 -22.9(3) . . . . ?
C12 N1 C4 C3 -30.2(4) . . . . ?
N2 N1 C4 C3 153.8(3) . . . . ?
N1 N2 C5 O1 -179.72(18) . . . . ?
N1 N2 C5 C18 -0.2(3) . . . . ?
C6 O1 C5 N2 12.5(3) . . . . ?
C6 O1 C5 C18 -167.14(19) . . . . ?
C7 O2 C6 O1 83.1(2) . . . . ?
C7 O2 C6 C19 -160.25(17) . . . . ?
C5 O1 C6 O2 -151.77(18) . . . . ?
C5 O1 C6 C19 93.8(2) . . . . ?
N4 N3 C7 O2 -179.36(18) . . . . ?
N4 N3 C7 C34 -1.7(3) . . . . ?
C6 O2 C7 N3 -7.8(3) . . . . ?
C6 O2 C7 C34 174.23(18) . . . . ?
N3 N4 C8 C26 17.2(3) . . . . ?
C28 N4 C8 C26 -164.1(2) . . . . ?
N3 N4 C8 C9 -159.1(2) . . . . ?
C28 N4 C8 C9 19.7(4) . . . . ?
C26 C8 C9 C10 0.4(5) . . . . ?
N4 C8 C9 C10 176.6(3) . . . . ?
C8 C9 C10 C11 -1.1(6) . . . . ?
C9 C10 C11 C27 0.7(6) . . . . ?
N2 N1 C12 O5 170.5(2) . . . . ?
C4 N1 C12 O5 -5.2(4) . . . . ?
N2 N1 C12 C13 -10.4(3) . . . . ?
C4 N1 C12 C13 174.0(2) . . . . ?
O5 C12 C13 C18 -175.0(2) . . . . ?
N1 C12 C13 C18 5.8(3) . . . . ?
O5 C12 C13 C14 4.9(4) . . . . ?
N1 C12 C13 C14 -174.3(2) . . . . ?
C18 C13 C14 C15 -0.5(4) . . . . ?
C12 C13 C14 C15 179.5(2) . . . . ?
C13 C14 C15 C16 -0.6(4) . . . . ?
C14 C15 C16 C17 1.4(5) . . . . ?
C15 C16 C17 C18 -1.1(4) . . . . ?
C16 C17 C18 C13 0.0(4) . . . . ?
C16 C17 C18 C5 180.0(2) . . . . ?
C14 C13 C18 C17 0.8(3) . . . . ?
C12 C13 C18 C17 -179.3(2) . . . . ?
C14 C13 C18 C5 -179.2(2) . . . . ?
C12 C13 C18 C5 0.8(3) . . . . ?
N2 C5 C18 C17 176.1(2) . . . . ?
O1 C5 C18 C17 -4.3(3) . . . . ?
N2 C5 C18 C13 -3.9(3) . . . . ?
O1 C5 C18 C13 175.68(19) . . . . ?
O2 C6 C19 O3 -123.4(2) . . . . ?
O1 C6 C19 O3 -7.2(3) . . . . ?
O2 C6 C19 C20 53.1(2) . . . . ?
O1 C6 C19 C20 169.24(18) . . . . ?
O3 C19 C20 C25 32.9(3) . . . . ?
C6 C19 C20 C25 -143.6(2) . . . . ?
O3 C19 C20 C21 -145.5(3) . . . . ?
C6 C19 C20 C21 38.0(3) . . . . ?
C25 C20 C21 C22 0.2(3) . . . . ?
C19 C20 C21 C22 178.6(2) . . . . ?
C25 C20 C21 Cl2 -177.30(18) . . . . ?
C19 C20 C21 Cl2 1.1(3) . . . . ?
C20 C21 C22 C23 0.4(4) . . . . ?
Cl2 C21 C22 C23 178.01(19) . . . . ?
C21 C22 C23 C24 -0.4(4) . . . . ?
C21 C22 C23 Cl1 179.49(18) . . . . ?
C22 C23 C24 C25 -0.2(4) . . . . ?
Cl1 C23 C24 C25 179.96(19) . . . . ?
C23 C24 C25 C20 0.8(4) . . . . ?
C21 C20 C25 C24 -0.8(4) . . . . ?
C19 C20 C25 C24 -179.4(2) . . . . ?
C9 C8 C26 C27 0.6(4) . . . . ?
N4 C8 C26 C27 -175.7(3) . . . . ?
C10 C11 C27 C26 0.3(6) . . . . ?
C8 C26 C27 C11 -0.9(5) . . . . ?
N3 N4 C28 O4 -175.9(3) . . . . ?
C8 N4 C28 O4 5.4(4) . . . . ?
N3 N4 C28 C29 2.9(3) . . . . ?
C8 N4 C28 C29 -175.8(2) . . . . ?
O4 C28 C29 C34 175.1(3) . . . . ?
N4 C28 C29 C34 -3.6(3) . . . . ?
O4 C28 C29 C30 -4.3(4) . . . . ?
N4 C28 C29 C30 176.9(2) . . . . ?
C34 C29 C30 C31 -0.8(4) . . . . ?
C28 C29 C30 C31 178.7(3) . . . . ?
C29 C30 C31 C32 -0.4(5) . . . . ?
C30 C31 C32 C33 0.8(5) . . . . ?
C31 C32 C33 C34 0.0(4) . . . . ?
C30 C29 C34 C33 1.6(4) . . . . ?
C28 C29 C34 C33 -177.8(2) . . . . ?
C30 C29 C34 C7 -178.6(2) . . . . ?
C28 C29 C34 C7 2.0(3) . . . . ?
C32 C33 C34 C29 -1.2(4) . . . . ?
C32 C33 C34 C7 179.0(2) . . . . ?
N3 C7 C34 C29 0.8(3) . . . . ?
O2 C7 C34 C29 178.55(19) . . . . ?
N3 C7 C34 C33 -179.4(2) . . . . ?
O2 C7 C34 C33 -1.7(3) . . . . ?
C3 C4 C35 C36 2.8(4) . . . . ?
N1 C4 C35 C36 179.5(2) . . . . ?
C2 C1 C36 C35 -1.0(5) . . . . ?
C4 C35 C36 C1 -0.9(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
C9 H14 O4 0.93 2.18 2.764(4) 120.2 .
C9 H14 Cl2 0.93 2.91 3.638(4) 135.8 2_666
C6 H12 Cl2 0.98 2.56 3.138(3) 117.6 .
C3 H4 O5 0.93 2.30 2.786(4) 112.1 .
C9 H14 O4 0.93 2.18 2.764(4) 120.2 .
C9 H14 Cl2 0.93 2.91 3.638(4) 135.8 2_666
C6 H12 Cl2 0.98 2.56 3.138(3) 117.6 .
C3 H4 O5 0.93 2.30 2.786(4) 112.1 .
C3 H4 O5 0.93 2.30 2.786(4) 112.1 .
C6 H12 Cl2 0.98 2.56 3.138(3) 117.6 .
C9 H14 Cl2 0.93 2.91 3.638(4) 135.8 2_666
C9 H14 O4 0.93 2.18 2.764(4) 120.2 .
C3 H4 O5 0.93 2.30 2.786(4) 112.1 .
C6 H12 Cl2 0.98 2.56 3.138(3) 117.6 .
C9 H14 Cl2 0.93 2.91 3.638(4) 135.8 2_666
C9 H14 O4 0.93 2.18 2.764(4) 120.2 .
C3 H4 O5 0.93 2.30 2.786(4) 112.1 .
C6 H12 Cl2 0.98 2.56 3.138(3) 117.6 .
C9 H14 Cl2 0.93 2.91 3.638(4) 135.8 2_666
C9 H14 O4 0.93 2.18 2.764(4) 120.2 .

_refine_diff_density_max         0.236
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.051

####################################################################### 
# 
# 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_MP
_database_code_depnum_ccdc_archive 'CCDC 2103982'
loop_
_audit_author_name
_audit_author_address
'RIYA BAG'
;UNIVERSITY OF CALCUTTA
India
;
_audit_update_record             
;
2021-08-18 deposited with the CCDC.	2022-03-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H23 Br N4 O5'
_chemical_formula_sum            'C36 H23 Br N4 O5'
_chemical_formula_weight         671.49

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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                   13.543(3)
_cell_length_b                   10.328(2)
_cell_length_c                   22.564(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.723(4)
_cell_angle_gamma                90
_cell_volume                     3101.0(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    8891
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      21.60

_exptl_crystal_description       Square
_exptl_crystal_colour            White
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_F_000             1368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.54
_exptl_crystal_size_min          0.48
_exptl_absorpt_coefficient_mu    1.376
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5198
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(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            44463
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_av_R_equivalents  0.0785
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.837
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_full        24.996
_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 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5462
_reflns_number_gt                3433
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_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)+(0.1000P)²+0.5157P] 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     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0098(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5462
_refine_ls_number_parameters     416
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0991
_refine_ls_R_factor_gt           0.0509
_refine_ls_wR_factor_ref         0.1749
_refine_ls_wR_factor_gt          0.1373
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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
Br1 Br 0.51573(6) -0.21865(5) 0.45230(3) 0.1233(4) Uani 1 1 d . . . . .
O1 O 0.58822(18) 0.5178(2) 0.31348(10) 0.0506(6) Uani 1 1 d . . . . .
O2 O 0.47981(17) 0.4341(2) 0.36896(9) 0.0494(6) Uani 1 1 d . . . . .
O3 O 0.58344(19) 0.6195(2) 0.08029(11) 0.0577(7) Uani 1 1 d . . . . .
O4 O 0.7117(2) 0.3479(3) 0.37218(13) 0.0736(8) Uani 1 1 d . . . . .
O5 O 0.1521(2) 0.6979(3) 0.26503(13) 0.0728(8) Uani 1 1 d . . . . .
N1 N 0.5882(2) 0.4776(3) 0.15803(12) 0.0447(7) Uani 1 1 d . . . . .
N2 N 0.5921(2) 0.4499(3) 0.21851(12) 0.0455(7) Uani 1 1 d . . . . .
N3 N 0.3814(2) 0.5216(3) 0.28644(12) 0.0460(7) Uani 1 1 d . . . . .
N4 N 0.2972(2) 0.5911(3) 0.26102(12) 0.0470(7) Uani 1 1 d . . . . .
C1 C 0.6241(4) 0.1425(4) 0.0600(2) 0.0757(13) Uani 1 1 d . . . . .
H1 H 0.631770 0.067342 0.038615 0.091 Uiso 1 1 calc R U . . .
C2 C 0.5577(3) 0.2356(4) 0.03485(18) 0.0620(10) Uani 1 1 d . . . . .
H23 H 0.519940 0.223190 -0.003588 0.074 Uiso 1 1 calc R U . . .
C3 C 0.5461(3) 0.3478(3) 0.06596(16) 0.0499(9) Uani 1 1 d . . . . .
H22 H 0.501439 0.411499 0.048428 0.060 Uiso 1 1 calc R U . . .
C4 C 0.6010(2) 0.3648(3) 0.12310(15) 0.0449(8) Uani 1 1 d . . . . .
C5 C 0.5835(2) 0.5439(3) 0.25360(15) 0.0451(8) Uani 1 1 d . . . . .
C6 C 0.5453(3) 0.4015(3) 0.32846(15) 0.0446(8) Uani 1 1 d . . . . .
H9 H 0.508536 0.358151 0.292362 0.054 Uiso 1 1 calc R U . . .
C7 C 0.3956(3) 0.5010(3) 0.34329(15) 0.0437(8) Uani 1 1 d . . . . .
C8 C 0.2943(2) 0.6112(3) 0.19752(15) 0.0462(8) Uani 1 1 d . . . . .
C9 C 0.2899(3) 0.7344(4) 0.17414(19) 0.0613(10) Uani 1 1 d . . . . .
H13 H 0.282500 0.805430 0.198242 0.074 Uiso 1 1 calc R U . . .
C10 C 0.2966(3) 0.7510(4) 0.1144(2) 0.0728(12) Uani 1 1 d . . . . .
H10 H 0.294877 0.834050 0.098347 0.087 Uiso 1 1 calc R U . . .
C11 C 0.3058(3) 0.6475(5) 0.07883(18) 0.0665(11) Uani 1 1 d . . . . .
H2 H 0.309452 0.659903 0.038475 0.080 Uiso 1 1 calc R U . . .
C12 C 0.6795(4) 0.1602(4) 0.1168(2) 0.0794(13) Uani 1 1 d . . . . .
H3 H 0.724735 0.096818 0.133937 0.095 Uiso 1 1 calc R U . . .
C13 C 0.6686(3) 0.2708(4) 0.14855(18) 0.0644(11) Uani 1 1 d . . . . .
H4 H 0.706461 0.282596 0.186998 0.077 Uiso 1 1 calc R U . . .
C14 C 0.5809(2) 0.6015(3) 0.13356(16) 0.0451(8) Uani 1 1 d . . . . .
C15 C 0.5706(2) 0.7046(3) 0.17574(16) 0.0462(8) Uani 1 1 d . . . . .
C16 C 0.5709(3) 0.6776(3) 0.23669(16) 0.0482(9) Uani 1 1 d . . . . .
C17 C 0.6252(3) 0.3129(3) 0.36347(15) 0.0445(8) Uani 1 1 d . . . . .
C18 C 0.5952(3) 0.1849(3) 0.38423(15) 0.0440(8) Uani 1 1 d . . . . .
C19 C 0.4969(3) 0.1436(4) 0.37584(18) 0.0568(10) Uani 1 1 d . . . . .
H5 H 0.445886 0.196847 0.356003 0.068 Uiso 1 1 calc R U . . .
C20 C 0.4733(3) 0.0240(4) 0.3966(2) 0.0699(12) Uani 1 1 d . . . . .
H8 H 0.406755 -0.003019 0.391375 0.084 Uiso 1 1 calc R U . . .
C21 C 0.5487(4) -0.0539(4) 0.42470(18) 0.0659(11) Uani 1 1 d . . . . .
C22 C 0.6472(4) -0.0165(4) 0.43322(19) 0.0740(12) Uani 1 1 d . . . . .
H7 H 0.697738 -0.071647 0.452024 0.089 Uiso 1 1 calc R U . . .
C23 C 0.6704(3) 0.1039(4) 0.41358(17) 0.0596(10) Uani 1 1 d . . . . .
H6 H 0.736971 0.131110 0.420016 0.071 Uiso 1 1 calc R U . . .
C24 C 0.3098(3) 0.5236(5) 0.10233(18) 0.0690(11) Uani 1 1 d . . . . .
H12 H 0.315698 0.452671 0.077826 0.083 Uiso 1 1 calc R U . . .
C25 C 0.3049(3) 0.5056(4) 0.16232(16) 0.0584(10) Uani 1 1 d . . . . .
H11 H 0.308746 0.422767 0.178734 0.070 Uiso 1 1 calc R U . . .
C26 C 0.2254(3) 0.6383(3) 0.29126(17) 0.0518(9) Uani 1 1 d . . . . .
C27 C 0.2458(3) 0.6136(3) 0.35654(16) 0.0486(9) Uani 1 1 d . . . . .
C28 C 0.3323(3) 0.5452(3) 0.38352(15) 0.0460(9) Uani 1 1 d . . . . .
C29 C 0.3518(3) 0.5228(4) 0.44524(16) 0.0543(9) Uani 1 1 d . . . . .
H14 H 0.408527 0.476474 0.462990 0.065 Uiso 1 1 calc R U . . .
C30 C 0.2863(4) 0.5700(4) 0.47988(19) 0.0691(12) Uani 1 1 d . . . . .
H15 H 0.298873 0.555433 0.521272 0.083 Uiso 1 1 calc R U . . .
C31 C 0.2017(4) 0.6389(4) 0.4536(2) 0.0744(12) Uani 1 1 d . . . . .
H17 H 0.158756 0.671900 0.477575 0.089 Uiso 1 1 calc R U . . .
C32 C 0.1811(3) 0.6588(4) 0.3928(2) 0.0643(11) Uani 1 1 d . . . . .
H16 H 0.123060 0.703053 0.375517 0.077 Uiso 1 1 calc R U . . .
C33 C 0.5584(3) 0.7768(4) 0.27630(19) 0.0679(11) Uani 1 1 d . . . . .
H21 H 0.558726 0.759021 0.316741 0.081 Uiso 1 1 calc R U . . .
C34 C 0.5457(4) 0.9018(4) 0.2548(2) 0.0812(14) Uani 1 1 d . . . . .
H20 H 0.536465 0.968531 0.280941 0.097 Uiso 1 1 calc R U . . .
C35 C 0.5465(4) 0.9291(4) 0.1952(2) 0.0820(14) Uani 1 1 d . . . . .
H19 H 0.538738 1.014146 0.181612 0.098 Uiso 1 1 calc R U . . .
C36 C 0.5585(3) 0.8329(4) 0.15590(19) 0.0633(11) Uani 1 1 d . . . . .
H18 H 0.558663 0.852537 0.115694 0.076 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
Br1 C21 1.893(4) . ?
O1 C5 1.368(4) . ?
O1 C6 1.403(4) . ?
O2 C7 1.367(4) . ?
O2 C6 1.427(4) . ?
O3 C14 1.223(4) . ?
O4 C17 1.207(4) . ?
O5 C26 1.223(4) . ?
N1 N2 1.386(4) . ?
N1 C14 1.389(4) . ?
N1 C4 1.435(4) . ?
N2 C5 1.272(4) . ?
N3 C7 1.279(4) . ?
N3 N4 1.379(4) . ?
N4 C26 1.377(4) . ?
N4 C8 1.441(4) . ?
C1 C2 1.365(6) . ?
C1 C12 1.373(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.379(5) . ?
C2 H23 0.9300 . ?
C3 C4 1.375(5) . ?
C3 H22 0.9300 . ?
C4 C13 1.384(5) . ?
C5 C16 1.434(5) . ?
C6 C17 1.521(5) . ?
C6 H9 0.9800 . ?
C7 C28 1.434(5) . ?
C8 C25 1.372(5) . ?
C8 C9 1.374(5) . ?
C9 C10 1.378(6) . ?
C9 H13 0.9300 . ?
C10 C11 1.357(6) . ?
C10 H10 0.9300 . ?
C11 C24 1.382(6) . ?
C11 H2 0.9300 . ?
C12 C13 1.370(6) . ?
C12 H3 0.9300 . ?
C13 H4 0.9300 . ?
C14 C15 1.452(5) . ?
C15 C36 1.398(5) . ?
C15 C16 1.403(5) . ?
C16 C33 1.390(5) . ?
C17 C18 1.484(5) . ?
C18 C19 1.377(5) . ?
C18 C23 1.388(5) . ?
C19 C20 1.378(5) . ?
C19 H5 0.9300 . ?
C20 C21 1.361(6) . ?
C20 H8 0.9300 . ?
C21 C22 1.367(6) . ?
C22 C23 1.376(5) . ?
C22 H7 0.9300 . ?
C23 H6 0.9300 . ?
C24 C25 1.380(5) . ?
C24 H12 0.9300 . ?
C25 H11 0.9300 . ?
C26 C27 1.470(5) . ?
C27 C32 1.387(5) . ?
C27 C28 1.406(5) . ?
C28 C29 1.388(5) . ?
C29 C30 1.376(5) . ?
C29 H14 0.9300 . ?
C30 C31 1.384(6) . ?
C30 H15 0.9300 . ?
C31 C32 1.363(6) . ?
C31 H17 0.9300 . ?
C32 H16 0.9300 . ?
C33 C34 1.379(5) . ?
C33 H21 0.9300 . ?
C34 C35 1.377(6) . ?
C34 H20 0.9300 . ?
C35 C36 1.362(6) . ?
C35 H19 0.9300 . ?
C36 H18 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
C5 O1 C6 117.5(3) . . ?
C7 O2 C6 114.6(2) . . ?
N2 N1 C14 124.6(3) . . ?
N2 N1 C4 112.8(2) . . ?
C14 N1 C4 122.4(3) . . ?
C5 N2 N1 117.7(3) . . ?
C7 N3 N4 117.5(3) . . ?
C26 N4 N3 125.7(3) . . ?
C26 N4 C8 123.4(3) . . ?
N3 N4 C8 110.9(2) . . ?
C2 C1 C12 119.9(4) . . ?
C2 C1 H1 120.1 . . ?
C12 C1 H1 120.1 . . ?
C1 C2 C3 120.6(4) . . ?
C1 C2 H23 119.7 . . ?
C3 C2 H23 119.7 . . ?
C4 C3 C2 119.4(3) . . ?
C4 C3 H22 120.3 . . ?
C2 C3 H22 120.3 . . ?
C3 C4 C13 120.0(3) . . ?
C3 C4 N1 121.3(3) . . ?
C13 C4 N1 118.7(3) . . ?
N2 C5 O1 118.2(3) . . ?
N2 C5 C16 126.1(3) . . ?
O1 C5 C16 115.7(3) . . ?
O1 C6 O2 106.7(3) . . ?
O1 C6 C17 110.7(3) . . ?
O2 C6 C17 106.0(3) . . ?
O1 C6 H9 111.1 . . ?
O2 C6 H9 111.1 . . ?
C17 C6 H9 111.1 . . ?
N3 C7 O2 117.8(3) . . ?
N3 C7 C28 125.9(3) . . ?
O2 C7 C28 116.3(3) . . ?
C25 C8 C9 121.0(3) . . ?
C25 C8 N4 118.3(3) . . ?
C9 C8 N4 120.4(3) . . ?
C8 C9 C10 119.0(4) . . ?
C8 C9 H13 120.5 . . ?
C10 C9 H13 120.5 . . ?
C11 C10 C9 120.7(4) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C24 120.2(4) . . ?
C10 C11 H2 119.9 . . ?
C24 C11 H2 119.9 . . ?
C13 C12 C1 120.4(4) . . ?
C13 C12 H3 119.8 . . ?
C1 C12 H3 119.8 . . ?
C12 C13 C4 119.7(4) . . ?
C12 C13 H4 120.1 . . ?
C4 C13 H4 120.1 . . ?
O3 C14 N1 121.2(3) . . ?
O3 C14 C15 123.8(3) . . ?
N1 C14 C15 115.0(3) . . ?
C36 C15 C16 118.8(3) . . ?
C36 C15 C14 120.3(3) . . ?
C16 C15 C14 120.9(3) . . ?
C33 C16 C15 120.3(3) . . ?
C33 C16 C5 124.1(3) . . ?
C15 C16 C5 115.5(3) . . ?
O4 C17 C18 122.0(3) . . ?
O4 C17 C6 118.7(3) . . ?
C18 C17 C6 119.3(3) . . ?
C19 C18 C23 118.9(3) . . ?
C19 C18 C17 123.2(3) . . ?
C23 C18 C17 117.9(3) . . ?
C18 C19 C20 120.7(4) . . ?
C18 C19 H5 119.7 . . ?
C20 C19 H5 119.7 . . ?
C21 C20 C19 119.1(4) . . ?
C21 C20 H8 120.4 . . ?
C19 C20 H8 120.4 . . ?
C20 C21 C22 121.7(4) . . ?
C20 C21 Br1 118.8(3) . . ?
C22 C21 Br1 119.4(3) . . ?
C21 C22 C23 119.0(4) . . ?
C21 C22 H7 120.5 . . ?
C23 C22 H7 120.5 . . ?
C22 C23 C18 120.5(4) . . ?
C22 C23 H6 119.7 . . ?
C18 C23 H6 119.7 . . ?
C25 C24 C11 119.7(4) . . ?
C25 C24 H12 120.2 . . ?
C11 C24 H12 120.2 . . ?
C8 C25 C24 119.4(4) . . ?
C8 C25 H11 120.3 . . ?
C24 C25 H11 120.3 . . ?
O5 C26 N4 121.5(3) . . ?
O5 C26 C27 123.8(3) . . ?
N4 C26 C27 114.6(3) . . ?
C32 C27 C28 118.7(4) . . ?
C32 C27 C26 120.8(4) . . ?
C28 C27 C26 120.5(3) . . ?
C29 C28 C27 120.4(3) . . ?
C29 C28 C7 123.9(3) . . ?
C27 C28 C7 115.7(3) . . ?
C30 C29 C28 119.2(4) . . ?
C30 C29 H14 120.4 . . ?
C28 C29 H14 120.4 . . ?
C29 C30 C31 120.5(4) . . ?
C29 C30 H15 119.7 . . ?
C31 C30 H15 119.7 . . ?
C32 C31 C30 120.5(4) . . ?
C32 C31 H17 119.8 . . ?
C30 C31 H17 119.8 . . ?
C31 C32 C27 120.6(4) . . ?
C31 C32 H16 119.7 . . ?
C27 C32 H16 119.7 . . ?
C34 C33 C16 119.1(4) . . ?
C34 C33 H21 120.4 . . ?
C16 C33 H21 120.4 . . ?
C35 C34 C33 120.8(4) . . ?
C35 C34 H20 119.6 . . ?
C33 C34 H20 119.6 . . ?
C36 C35 C34 120.7(4) . . ?
C36 C35 H19 119.6 . . ?
C34 C35 H19 119.6 . . ?
C35 C36 C15 120.3(4) . . ?
C35 C36 H18 119.9 . . ?
C15 C36 H18 119.9 . . ?

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
C14 N1 N2 C5 3.6(5) . . . . ?
C4 N1 N2 C5 178.7(3) . . . . ?
C7 N3 N4 C26 -1.4(5) . . . . ?
C7 N3 N4 C8 177.3(3) . . . . ?
C12 C1 C2 C3 0.4(7) . . . . ?
C1 C2 C3 C4 -0.9(6) . . . . ?
C2 C3 C4 C13 1.1(5) . . . . ?
C2 C3 C4 N1 -177.4(3) . . . . ?
N2 N1 C4 C3 140.9(3) . . . . ?
C14 N1 C4 C3 -43.9(5) . . . . ?
N2 N1 C4 C13 -37.7(4) . . . . ?
C14 N1 C4 C13 137.5(3) . . . . ?
N1 N2 C5 O1 -179.4(2) . . . . ?
N1 N2 C5 C16 -0.6(5) . . . . ?
C6 O1 C5 N2 -36.2(4) . . . . ?
C6 O1 C5 C16 144.9(3) . . . . ?
C5 O1 C6 O2 -128.9(3) . . . . ?
C5 O1 C6 C17 116.2(3) . . . . ?
C7 O2 C6 O1 69.5(3) . . . . ?
C7 O2 C6 C17 -172.5(3) . . . . ?
N4 N3 C7 O2 -179.0(3) . . . . ?
N4 N3 C7 C28 -0.8(5) . . . . ?
C6 O2 C7 N3 3.5(4) . . . . ?
C6 O2 C7 C28 -174.8(3) . . . . ?
C26 N4 C8 C25 -129.5(4) . . . . ?
N3 N4 C8 C25 51.8(4) . . . . ?
C26 N4 C8 C9 56.1(5) . . . . ?
N3 N4 C8 C9 -122.6(3) . . . . ?
C25 C8 C9 C10 -0.2(6) . . . . ?
N4 C8 C9 C10 174.0(3) . . . . ?
C8 C9 C10 C11 1.1(6) . . . . ?
C9 C10 C11 C24 -0.8(6) . . . . ?
C2 C1 C12 C13 0.0(7) . . . . ?
C1 C12 C13 C4 0.2(7) . . . . ?
C3 C4 C13 C12 -0.8(6) . . . . ?
N1 C4 C13 C12 177.7(4) . . . . ?
N2 N1 C14 O3 175.9(3) . . . . ?
C4 N1 C14 O3 1.2(5) . . . . ?
N2 N1 C14 C15 -3.9(4) . . . . ?
C4 N1 C14 C15 -178.6(3) . . . . ?
O3 C14 C15 C36 2.8(5) . . . . ?
N1 C14 C15 C36 -177.4(3) . . . . ?
O3 C14 C15 C16 -178.3(3) . . . . ?
N1 C14 C15 C16 1.5(5) . . . . ?
C36 C15 C16 C33 0.5(5) . . . . ?
C14 C15 C16 C33 -178.4(3) . . . . ?
C36 C15 C16 C5 179.9(3) . . . . ?
C14 C15 C16 C5 1.0(5) . . . . ?
N2 C5 C16 C33 177.8(4) . . . . ?
O1 C5 C16 C33 -3.4(5) . . . . ?
N2 C5 C16 C15 -1.6(5) . . . . ?
O1 C5 C16 C15 177.2(3) . . . . ?
O1 C6 C17 O4 -2.4(4) . . . . ?
O2 C6 C17 O4 -117.8(3) . . . . ?
O1 C6 C17 C18 179.4(3) . . . . ?
O2 C6 C17 C18 64.1(4) . . . . ?
O4 C17 C18 C19 178.8(3) . . . . ?
C6 C17 C18 C19 -3.1(5) . . . . ?
O4 C17 C18 C23 -1.1(5) . . . . ?
C6 C17 C18 C23 177.0(3) . . . . ?
C23 C18 C19 C20 0.4(5) . . . . ?
C17 C18 C19 C20 -179.4(3) . . . . ?
C18 C19 C20 C21 -1.0(6) . . . . ?
C19 C20 C21 C22 0.3(7) . . . . ?
C19 C20 C21 Br1 -179.4(3) . . . . ?
C20 C21 C22 C23 0.9(7) . . . . ?
Br1 C21 C22 C23 -179.3(3) . . . . ?
C21 C22 C23 C18 -1.5(6) . . . . ?
C19 C18 C23 C22 0.9(6) . . . . ?
C17 C18 C23 C22 -179.3(4) . . . . ?
C10 C11 C24 C25 -0.3(6) . . . . ?
C9 C8 C25 C24 -0.9(6) . . . . ?
N4 C8 C25 C24 -175.3(3) . . . . ?
C11 C24 C25 C8 1.2(6) . . . . ?
N3 N4 C26 O5 -179.1(3) . . . . ?
C8 N4 C26 O5 2.3(5) . . . . ?
N3 N4 C26 C27 2.1(5) . . . . ?
C8 N4 C26 C27 -176.4(3) . . . . ?
O5 C26 C27 C32 -0.4(5) . . . . ?
N4 C26 C27 C32 178.3(3) . . . . ?
O5 C26 C27 C28 -179.5(3) . . . . ?
N4 C26 C27 C28 -0.7(5) . . . . ?
C32 C27 C28 C29 0.4(5) . . . . ?
C26 C27 C28 C29 179.5(3) . . . . ?
C32 C27 C28 C7 179.8(3) . . . . ?
C26 C27 C28 C7 -1.1(5) . . . . ?
N3 C7 C28 C29 -178.6(3) . . . . ?
O2 C7 C28 C29 -0.4(5) . . . . ?
N3 C7 C28 C27 2.0(5) . . . . ?
O2 C7 C28 C27 -179.8(3) . . . . ?
C27 C28 C29 C30 -0.9(5) . . . . ?
C7 C28 C29 C30 179.7(3) . . . . ?
C28 C29 C30 C31 0.0(6) . . . . ?
C29 C30 C31 C32 1.4(6) . . . . ?
C30 C31 C32 C27 -1.9(6) . . . . ?
C28 C27 C32 C31 1.0(6) . . . . ?
C26 C27 C32 C31 -178.1(3) . . . . ?
C15 C16 C33 C34 0.1(6) . . . . ?
C5 C16 C33 C34 -179.2(4) . . . . ?
C16 C33 C34 C35 -0.8(7) . . . . ?
C33 C34 C35 C36 0.9(8) . . . . ?
C34 C35 C36 C15 -0.2(7) . . . . ?
C16 C15 C36 C35 -0.5(6) . . . . ?
C14 C15 C36 C35 178.4(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
C25 H11 O5 0.93 2.65 3.574(5) 171.0 2_545
C25 H11 O5 0.93 2.65 3.574(5) 171.0 2_545
C25 H11 O5 0.93 2.65 3.574(5) 171.0 2_545
C25 H11 O5 0.93 2.65 3.574(5) 171.0 2_545
C25 H11 O5 0.93 2.65 3.574(5) 171.0 2_545
C25 H11 O5 0.93 2.65 3.574(5) 171.0 2_545
C25 H11 O5 0.93 2.65 3.574(5) 171.0 2_545
C25 H11 O5 0.93 2.65 3.574(5) 171.0 2_545

_refine_diff_density_max         0.410
_refine_diff_density_min         -0.533
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_OP
_database_code_depnum_ccdc_archive 'CCDC 2103983'
loop_
_audit_author_name
_audit_author_address
'RIYA BAG'
;UNIVERSITY OF CALCUTTA
India
;
_audit_update_record             
;
2021-08-18 deposited with the CCDC.	2022-03-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H9 N O2'
_chemical_formula_sum            'C14 H9 N O2'
_chemical_formula_weight         223.22

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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   11.6817(8)
_cell_length_b                   7.6497(6)
_cell_length_c                   23.7774(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2124.8(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7530
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      25.85

_exptl_crystal_description       Square
_exptl_crystal_colour            White
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.54
_exptl_crystal_size_min          0.48
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_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       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20151
_diffrn_reflns_av_unetI/netI     0.0155
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.713
_diffrn_reflns_theta_max         24.992
_diffrn_reflns_theta_full        24.992
_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 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1864
_reflns_number_gt                1642
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_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)+(0.1000P)²+0.2203P] 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     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.022(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1864
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0310
_refine_ls_wR_factor_ref         0.1199
_refine_ls_wR_factor_gt          0.1088
_refine_ls_goodness_of_fit_ref   0.936
_refine_ls_restrained_S_all      0.936
_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
O1 O 0.22032(8) 0.50669(14) 0.58899(4) 0.0582(3) Uani 1 1 d . . . . .
O2 O 0.55647(8) 0.20527(14) 0.60835(4) 0.0575(3) Uani 1 1 d . . . . .
N1 N 0.38821(8) 0.36540(12) 0.61395(4) 0.0384(3) Uani 1 1 d . . . . .
C1 C 0.36203(14) 0.42910(19) 0.78849(6) 0.0537(4) Uani 1 1 d . . . . .
H1 H 0.355568 0.445591 0.827115 0.064 Uiso 1 1 calc R U . . .
C2 C 0.27626(13) 0.3451(2) 0.75944(6) 0.0542(4) Uani 1 1 d . . . . .
H7 H 0.212166 0.304156 0.778547 0.065 Uiso 1 1 calc R U . . .
C3 C 0.28505(11) 0.32118(18) 0.70171(6) 0.0467(4) Uani 1 1 d . . . . .
H8 H 0.227524 0.263364 0.682087 0.056 Uiso 1 1 calc R U . . .
C4 C 0.37988(10) 0.38401(15) 0.67381(5) 0.0381(3) Uani 1 1 d . . . . .
C5 C 0.47612(10) 0.27473(16) 0.58581(5) 0.0391(3) Uani 1 1 d . . . . .
C6 C 0.44767(10) 0.28588(15) 0.52496(5) 0.0383(3) Uani 1 1 d . . . . .
C7 C 0.50489(12) 0.22132(17) 0.47868(5) 0.0462(4) Uani 1 1 d . . . . .
H6 H 0.573228 0.160111 0.482519 0.055 Uiso 1 1 calc R U . . .
C8 C 0.45666(12) 0.2511(2) 0.42605(6) 0.0510(4) Uani 1 1 d . . . . .
H2 H 0.493118 0.208484 0.394094 0.061 Uiso 1 1 calc R U . . .
C9 C 0.45735(12) 0.4887(2) 0.76042(6) 0.0555(4) Uani 1 1 d . . . . .
H9 H 0.515772 0.543818 0.780209 0.067 Uiso 1 1 calc R U . . .
C10 C 0.46651(11) 0.46701(18) 0.70305(5) 0.0476(4) Uani 1 1 d . . . . .
H3 H 0.530740 0.508055 0.684080 0.057 Uiso 1 1 calc R U . . .
C11 C 0.30597(10) 0.42792(16) 0.57632(5) 0.0401(3) Uani 1 1 d . . . . .
C12 C 0.34665(10) 0.37801(15) 0.51933(5) 0.0379(3) Uani 1 1 d . . . . .
C13 C 0.35530(12) 0.3431(2) 0.42051(5) 0.0505(4) Uani 1 1 d . . . . .
H4 H 0.324562 0.360860 0.384881 0.061 Uiso 1 1 calc R U . . .
C14 C 0.29875(11) 0.40927(18) 0.46717(5) 0.0461(4) Uani 1 1 d . . . . .
H5 H 0.231109 0.472337 0.463479 0.055 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 C11 1.2062(15) . ?
O2 C5 1.2044(15) . ?
N1 C11 1.3972(15) . ?
N1 C5 1.4083(15) . ?
N1 C4 1.4339(15) . ?
C1 C9 1.376(2) . ?
C1 C2 1.376(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.3885(19) . ?
C2 H7 0.9300 . ?
C3 C4 1.3778(18) . ?
C3 H8 0.9300 . ?
C4 C10 1.3822(17) . ?
C5 C6 1.4871(16) . ?
C6 C7 1.3788(17) . ?
C6 C12 1.3811(18) . ?
C7 C8 1.3912(18) . ?
C7 H6 0.9300 . ?
C8 C13 1.384(2) . ?
C8 H2 0.9300 . ?
C9 C10 1.3783(18) . ?
C9 H9 0.9300 . ?
C10 H3 0.9300 . ?
C11 C12 1.4858(17) . ?
C12 C14 1.3815(17) . ?
C13 C14 1.387(2) . ?
C13 H4 0.9300 . ?
C14 H5 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
C11 N1 C5 111.46(10) . . ?
C11 N1 C4 123.72(10) . . ?
C5 N1 C4 124.75(10) . . ?
C9 C1 C2 120.02(13) . . ?
C9 C1 H1 120.0 . . ?
C2 C1 H1 120.0 . . ?
C1 C2 C3 120.25(13) . . ?
C1 C2 H7 119.9 . . ?
C3 C2 H7 119.9 . . ?
C4 C3 C2 119.31(12) . . ?
C4 C3 H8 120.3 . . ?
C2 C3 H8 120.3 . . ?
C3 C4 C10 120.45(12) . . ?
C3 C4 N1 119.86(11) . . ?
C10 C4 N1 119.68(11) . . ?
O2 C5 N1 125.05(11) . . ?
O2 C5 C6 129.23(11) . . ?
N1 C5 C6 105.72(10) . . ?
C7 C6 C12 121.31(11) . . ?
C7 C6 C5 130.36(12) . . ?
C12 C6 C5 108.33(10) . . ?
C6 C7 C8 117.58(13) . . ?
C6 C7 H6 121.2 . . ?
C8 C7 H6 121.2 . . ?
C13 C8 C7 121.03(12) . . ?
C13 C8 H2 119.5 . . ?
C7 C8 H2 119.5 . . ?
C1 C9 C10 120.20(13) . . ?
C1 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C9 C10 C4 119.75(12) . . ?
C9 C10 H3 120.1 . . ?
C4 C10 H3 120.1 . . ?
O1 C11 N1 125.54(11) . . ?
O1 C11 C12 128.43(11) . . ?
N1 C11 C12 106.03(10) . . ?
C6 C12 C14 121.42(12) . . ?
C6 C12 C11 108.43(10) . . ?
C14 C12 C11 130.15(12) . . ?
C8 C13 C14 121.13(12) . . ?
C8 C13 H4 119.4 . . ?
C14 C13 H4 119.4 . . ?
C12 C14 C13 117.53(13) . . ?
C12 C14 H5 121.2 . . ?
C13 C14 H5 121.2 . . ?

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
C9 C1 C2 C3 -0.5(2) . . . . ?
C1 C2 C3 C4 -0.7(2) . . . . ?
C2 C3 C4 C10 1.25(19) . . . . ?
C2 C3 C4 N1 -177.90(12) . . . . ?
C11 N1 C4 C3 56.18(16) . . . . ?
C5 N1 C4 C3 -120.30(13) . . . . ?
C11 N1 C4 C10 -122.98(13) . . . . ?
C5 N1 C4 C10 60.55(15) . . . . ?
C11 N1 C5 O2 -178.70(12) . . . . ?
C4 N1 C5 O2 -1.85(19) . . . . ?
C11 N1 C5 C6 1.62(13) . . . . ?
C4 N1 C5 C6 178.47(10) . . . . ?
O2 C5 C6 C7 -0.3(2) . . . . ?
N1 C5 C6 C7 179.39(13) . . . . ?
O2 C5 C6 C12 179.72(13) . . . . ?
N1 C5 C6 C12 -0.62(13) . . . . ?
C12 C6 C7 C8 -0.52(19) . . . . ?
C5 C6 C7 C8 179.47(12) . . . . ?
C6 C7 C8 C13 0.4(2) . . . . ?
C2 C1 C9 C10 1.0(2) . . . . ?
C1 C9 C10 C4 -0.4(2) . . . . ?
C3 C4 C10 C9 -0.70(19) . . . . ?
N1 C4 C10 C9 178.45(12) . . . . ?
C5 N1 C11 O1 178.32(12) . . . . ?
C4 N1 C11 O1 1.43(19) . . . . ?
C5 N1 C11 C12 -1.93(13) . . . . ?
C4 N1 C11 C12 -178.82(10) . . . . ?
C7 C6 C12 C14 0.01(19) . . . . ?
C5 C6 C12 C14 -179.98(11) . . . . ?
C7 C6 C12 C11 179.46(11) . . . . ?
C5 C6 C12 C11 -0.53(13) . . . . ?
O1 C11 C12 C6 -178.77(13) . . . . ?
N1 C11 C12 C6 1.49(13) . . . . ?
O1 C11 C12 C14 0.6(2) . . . . ?
N1 C11 C12 C14 -179.12(12) . . . . ?
C7 C8 C13 C14 0.3(2) . . . . ?
C6 C12 C14 C13 0.6(2) . . . . ?
C11 C12 C14 C13 -178.68(12) . . . . ?
C8 C13 C14 C12 -0.8(2) . . . . ?

_refine_diff_density_max         0.179
_refine_diff_density_min         -0.126
_refine_diff_density_rms         0.031

