# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_mr_nif
_database_code_depnum_ccdc_archive 'CCDC 2385548'
loop_
_audit_author_name
_audit_author_address
'kenguva gowtham'
;ICTIOCB
India
;
_audit_update_record             
;
2024-09-21 deposited with the CCDC.	2024-11-25 downloaded from the CCDC.
;
_audit_creation_date             2023-11-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H9 F3 N2 O2, C12 H9 N3 O'
_chemical_formula_sum            'C25 H18 F3 N5 O3'
_chemical_formula_weight         493.44
_chemical_melting_point          ?
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'
F F 0.0171 0.0103 '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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.7282(9)
_cell_length_b                   10.7734(9)
_cell_length_c                   11.9845(11)
_cell_angle_alpha                85.550(2)
_cell_angle_beta                 65.237(2)
_cell_angle_gamma                64.849(2)
_cell_volume                     1130.01(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2954
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      0.982
_cell_measurement_theta_min      0.977
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            26687
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        24.942
_diffrn_reflns_theta_max         24.942
_diffrn_reflns_theta_min         2.280
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 quest photon detector'
_diffrn_measurement_method       'Omega and Phi scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2954
_reflns_number_total             3938
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SHELXL'
_computing_data_collection       'Bruker APEX4'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         3938
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0502
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0533P)²+0.6529P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1207
_refine_ls_wR_factor_ref         0.1397
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2A), C5(H5), C9(H9), C11(H11), C15(H15), C17(H17), C19(H19), C23(H23),
 C4(H4), C7(H7), C14(H14), C20(H20), C22(H22)
2.b Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
F1 F 0.1664(2) 0.0958(2) -0.09539(19) 0.1072(7) Uani 1 1 d . . . . .
F2 F 0.0758(4) 0.0421(3) 0.0810(2) 0.1453(12) Uani 1 1 d . . . . .
F3 F -0.0629(2) 0.2102(2) 0.0210(3) 0.1194(9) Uani 1 1 d . . . . .
O2 O 0.2259(2) 0.3063(2) 0.65828(18) 0.0613(5) Uani 1 1 d . . . . .
H2 H 0.277644 0.345036 0.657039 0.092 Uiso 1 1 calc R U . . .
O3 O 0.2269(2) 0.41235(19) 0.49123(16) 0.0561(5) Uani 1 1 d . . . . .
N2 N 0.1170(2) 0.3391(2) 0.35851(19) 0.0492(5) Uani 1 1 d . . . . .
H2A H 0.159205 0.386060 0.370101 0.059 Uiso 1 1 calc R U . . .
N5 N -0.0347(2) 0.2252(2) 0.4557(2) 0.0524(5) Uani 1 1 d . . . . .
C2 C 0.1223(3) 0.3360(2) 0.2401(2) 0.0458(6) Uani 1 1 d . . . . .
C3 C 0.0725(4) 0.1488(3) 0.0217(3) 0.0648(8) Uani 1 1 d . . . . .
C5 C 0.1657(3) 0.4289(3) 0.1649(3) 0.0564(7) Uani 1 1 d . . . . .
H5 H 0.184822 0.491981 0.196035 0.068 Uiso 1 1 calc R U . . .
C9 C -0.0689(3) 0.1585(3) 0.6573(3) 0.0619(7) Uani 1 1 d . . . . .
H9 H -0.112755 0.116445 0.723206 0.074 Uiso 1 1 calc R U . . .
C11 C 0.1808(4) 0.4288(3) 0.0452(3) 0.0678(8) Uani 1 1 d . . . . .
H11 H 0.209653 0.491987 -0.003449 0.081 Uiso 1 1 calc R U . . .
C13 C 0.1856(3) 0.3390(2) 0.5667(2) 0.0459(6) Uani 1 1 d . . . . .
C15 C 0.0246(3) 0.2136(3) 0.6607(2) 0.0538(6) Uani 1 1 d . . . . .
H15 H 0.045395 0.208029 0.729313 0.065 Uiso 1 1 calc R U . . .
C17 C 0.0944(3) 0.2422(3) 0.1913(2) 0.0504(6) Uani 1 1 d . . . . .
H17 H 0.065978 0.178518 0.239392 0.061 Uiso 1 1 calc R U . . .
C18 C 0.0552(3) 0.2793(2) 0.4590(2) 0.0425(5) Uani 1 1 d . . . . .
C19 C -0.0949(3) 0.1679(3) 0.5537(3) 0.0586(7) Uani 1 1 d . . . . .
H19 H -0.158931 0.131840 0.551878 0.070 Uiso 1 1 calc R U . . .
C21 C 0.1096(3) 0.2448(3) 0.0706(2) 0.0544(6) Uani 1 1 d . . . . .
C23 C 0.1538(3) 0.3363(3) -0.0038(3) 0.0682(8) Uani 1 1 d . . . . .
H23 H 0.165102 0.335648 -0.085076 0.082 Uiso 1 1 calc R U . . .
C25 C 0.0876(3) 0.2771(2) 0.5624(2) 0.0428(5) Uani 1 1 d . . . . .
O1 O 0.5559(2) 1.06107(17) 0.85416(15) 0.0544(5) Uani 1 1 d . . . . .
N1 N 0.4868(2) 0.88439(19) 0.90803(18) 0.0407(4) Uani 1 1 d . . . . .
H1 H 0.472(3) 0.906(3) 0.987(3) 0.059(8) Uiso 1 1 d . . . . .
N3 N 0.6191(3) 1.0953(2) 0.5398(2) 0.0609(6) Uani 1 1 d . . . . .
N4 N 0.3670(2) 0.4450(2) 0.67510(19) 0.0483(5) Uani 1 1 d . . . . .
C1 C 0.4326(2) 0.6472(2) 0.73800(19) 0.0363(5) Uani 1 1 d . . . . .
C4 C 0.5022(2) 0.8441(2) 0.6828(2) 0.0376(5) Uani 1 1 d . . . . .
H4 H 0.504714 0.832148 0.605767 0.045 Uiso 1 1 calc R U . . .
C6 C 0.5804(3) 1.0297(2) 0.6140(2) 0.0418(5) Uani 1 1 d . . . . .
C7 C 0.4638(3) 0.4141(2) 0.7267(2) 0.0502(6) Uani 1 1 d . . . . .
H7 H 0.508402 0.323624 0.742439 0.060 Uiso 1 1 calc R U . . .
C8 C 0.4644(2) 0.7570(2) 0.77122(19) 0.0362(5) Uani 1 1 d . . . . .
C10 C 0.4551(2) 0.7817(2) 0.8863(2) 0.0374(5) Uani 1 1 d . . . . .
C12 C 0.5353(2) 0.9459(2) 0.70634(19) 0.0366(5) Uani 1 1 d . . . . .
C14 C 0.3365(3) 0.6775(2) 0.6804(2) 0.0452(6) Uani 1 1 d . . . . .
H14 H 0.291855 0.766625 0.662009 0.054 Uiso 1 1 calc R U . . .
C16 C 0.5289(3) 0.9700(2) 0.8248(2) 0.0400(5) Uani 1 1 d . . . . .
C20 C 0.5002(3) 0.5105(2) 0.7575(2) 0.0455(6) Uani 1 1 d . . . . .
H20 H 0.570173 0.484097 0.791398 0.055 Uiso 1 1 calc R U . . .
C22 C 0.3075(3) 0.5747(3) 0.6507(2) 0.0503(6) Uani 1 1 d . . . . .
H22 H 0.243205 0.596814 0.611674 0.060 Uiso 1 1 calc R U . . .
C24 C 0.4057(3) 0.7087(3) 0.9955(2) 0.0512(6) Uani 1 1 d . . . . .
H24A H 0.493766 0.636048 1.000711 0.077 Uiso 1 1 calc R U . . .
H24B H 0.344154 0.670010 0.986586 0.077 Uiso 1 1 calc R U . . .
H24C H 0.347461 0.773017 1.069625 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
F1 C3 1.327(3) . ?
F2 C3 1.299(4) . ?
F3 C3 1.319(3) . ?
O2 H2 0.8200 . ?
O2 C13 1.312(3) . ?
O3 C13 1.221(3) . ?
N2 H2A 0.8600 . ?
N2 C2 1.399(3) . ?
N2 C18 1.371(3) . ?
N5 C18 1.337(3) . ?
N5 C19 1.330(3) . ?
C2 C5 1.392(3) . ?
C2 C17 1.395(3) . ?
C3 C21 1.488(4) . ?
C5 H5 0.9300 . ?
C5 C11 1.375(4) . ?
C9 H9 0.9300 . ?
C9 C15 1.379(4) . ?
C9 C19 1.370(4) . ?
C11 H11 0.9300 . ?
C11 C23 1.379(4) . ?
C13 C25 1.483(3) . ?
C15 H15 0.9300 . ?
C15 C25 1.383(3) . ?
C17 H17 0.9300 . ?
C17 C21 1.386(4) . ?
C18 C25 1.416(3) . ?
C19 H19 0.9300 . ?
C21 C23 1.378(4) . ?
C23 H23 0.9300 . ?
O1 C16 1.245(3) . ?
N1 H1 0.92(3) . ?
N1 C10 1.359(3) . ?
N1 C16 1.372(3) . ?
N3 C6 1.143(3) . ?
N4 C7 1.335(3) . ?
N4 C22 1.334(3) . ?
C1 C8 1.485(3) . ?
C1 C14 1.386(3) . ?
C1 C20 1.389(3) . ?
C4 H4 0.9300 . ?
C4 C8 1.406(3) . ?
C4 C12 1.368(3) . ?
C6 C12 1.428(3) . ?
C7 H7 0.9300 . ?
C7 C20 1.376(3) . ?
C8 C10 1.379(3) . ?
C10 C24 1.492(3) . ?
C12 C16 1.432(3) . ?
C14 H14 0.9300 . ?
C14 C22 1.377(3) . ?
C20 H20 0.9300 . ?
C22 H22 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 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
C13 O2 H2 109.5 . . ?
C2 N2 H2A 114.8 . . ?
C18 N2 H2A 114.8 . . ?
C18 N2 C2 130.4(2) . . ?
C19 N5 C18 117.9(2) . . ?
C5 C2 N2 117.0(2) . . ?
C5 C2 C17 118.5(2) . . ?
C17 C2 N2 124.4(2) . . ?
F1 C3 C21 113.6(3) . . ?
F2 C3 F1 104.6(3) . . ?
F2 C3 F3 106.7(3) . . ?
F2 C3 C21 114.6(2) . . ?
F3 C3 F1 103.7(2) . . ?
F3 C3 C21 112.6(2) . . ?
C2 C5 H5 119.5 . . ?
C11 C5 C2 120.9(3) . . ?
C11 C5 H5 119.5 . . ?
C15 C9 H9 121.1 . . ?
C19 C9 H9 121.1 . . ?
C19 C9 C15 117.7(2) . . ?
C5 C11 H11 119.6 . . ?
C5 C11 C23 120.9(3) . . ?
C23 C11 H11 119.6 . . ?
O2 C13 C25 113.9(2) . . ?
O3 C13 O2 122.8(2) . . ?
O3 C13 C25 123.3(2) . . ?
C9 C15 H15 119.8 . . ?
C9 C15 C25 120.3(2) . . ?
C25 C15 H15 119.8 . . ?
C2 C17 H17 120.3 . . ?
C21 C17 C2 119.4(2) . . ?
C21 C17 H17 120.3 . . ?
N2 C18 C25 119.6(2) . . ?
N5 C18 N2 118.2(2) . . ?
N5 C18 C25 122.2(2) . . ?
N5 C19 C9 124.4(2) . . ?
N5 C19 H19 117.8 . . ?
C9 C19 H19 117.8 . . ?
C17 C21 C3 118.9(2) . . ?
C23 C21 C3 119.2(2) . . ?
C23 C21 C17 121.9(3) . . ?
C11 C23 H23 120.8 . . ?
C21 C23 C11 118.4(3) . . ?
C21 C23 H23 120.8 . . ?
C15 C25 C13 120.5(2) . . ?
C15 C25 C18 117.4(2) . . ?
C18 C25 C13 122.2(2) . . ?
C10 N1 H1 119.3(16) . . ?
C10 N1 C16 126.18(19) . . ?
C16 N1 H1 114.3(16) . . ?
C22 N4 C7 117.38(19) . . ?
C14 C1 C8 120.20(19) . . ?
C14 C1 C20 116.85(19) . . ?
C20 C1 C8 122.89(19) . . ?
C8 C4 H4 118.9 . . ?
C12 C4 H4 118.9 . . ?
C12 C4 C8 122.23(19) . . ?
N3 C6 C12 178.8(3) . . ?
N4 C7 H7 118.6 . . ?
N4 C7 C20 122.7(2) . . ?
C20 C7 H7 118.6 . . ?
C4 C8 C1 119.07(18) . . ?
C10 C8 C1 123.58(19) . . ?
C10 C8 C4 117.32(18) . . ?
N1 C10 C8 119.39(19) . . ?
N1 C10 C24 114.70(19) . . ?
C8 C10 C24 125.85(19) . . ?
C4 C12 C6 121.77(19) . . ?
C4 C12 C16 120.61(19) . . ?
C6 C12 C16 117.61(19) . . ?
C1 C14 H14 120.2 . . ?
C22 C14 C1 119.5(2) . . ?
C22 C14 H14 120.2 . . ?
O1 C16 N1 121.08(19) . . ?
O1 C16 C12 124.7(2) . . ?
N1 C16 C12 114.22(19) . . ?
C1 C20 H20 120.0 . . ?
C7 C20 C1 120.0(2) . . ?
C7 C20 H20 120.0 . . ?
N4 C22 C14 123.3(2) . . ?
N4 C22 H22 118.3 . . ?
C14 C22 H22 118.3 . . ?
C10 C24 H24A 109.5 . . ?
C10 C24 H24B 109.5 . . ?
C10 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

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
O2 H2 N4 0.82 1.79 2.606(2) 171.4 . yes
N2 H2A O3 0.86 1.96 2.665(2) 138.6 . yes
N1 H1 O1 0.92(3) 1.84(3) 2.759(2) 177(2) 2_677 yes

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
F1 C3 C21 C17 -141.1(3) . . . . ?
F1 C3 C21 C23 40.7(4) . . . . ?
F2 C3 C21 C17 -21.0(4) . . . . ?
F2 C3 C21 C23 160.8(3) . . . . ?
F3 C3 C21 C17 101.3(3) . . . . ?
F3 C3 C21 C23 -76.9(3) . . . . ?
O2 C13 C25 C15 11.3(3) . . . . ?
O2 C13 C25 C18 -168.3(2) . . . . ?
O3 C13 C25 C15 -169.6(2) . . . . ?
O3 C13 C25 C18 10.8(4) . . . . ?
N2 C2 C5 C11 177.0(2) . . . . ?
N2 C2 C17 C21 -177.1(2) . . . . ?
N2 C18 C25 C13 0.7(3) . . . . ?
N2 C18 C25 C15 -179.0(2) . . . . ?
N5 C18 C25 C13 -179.1(2) . . . . ?
N5 C18 C25 C15 1.3(3) . . . . ?
C2 N2 C18 N5 -11.4(4) . . . . ?
C2 N2 C18 C25 168.9(2) . . . . ?
C2 C5 C11 C23 -0.2(4) . . . . ?
C2 C17 C21 C3 -177.1(2) . . . . ?
C2 C17 C21 C23 1.0(4) . . . . ?
C3 C21 C23 C11 177.0(3) . . . . ?
C5 C2 C17 C21 -0.5(4) . . . . ?
C5 C11 C23 C21 0.7(4) . . . . ?
C9 C15 C25 C13 178.7(2) . . . . ?
C9 C15 C25 C18 -1.6(4) . . . . ?
C15 C9 C19 N5 0.8(4) . . . . ?
C17 C2 C5 C11 0.1(4) . . . . ?
C17 C21 C23 C11 -1.1(4) . . . . ?
C18 N2 C2 C5 167.5(2) . . . . ?
C18 N2 C2 C17 -15.8(4) . . . . ?
C18 N5 C19 C9 -1.2(4) . . . . ?
C19 N5 C18 N2 -179.7(2) . . . . ?
C19 N5 C18 C25 0.1(4) . . . . ?
C19 C9 C15 C25 0.7(4) . . . . ?
N4 C7 C20 C1 1.6(4) . . . . ?
C1 C8 C10 N1 179.8(2) . . . . ?
C1 C8 C10 C24 -3.0(4) . . . . ?
C1 C14 C22 N4 0.4(4) . . . . ?
C4 C8 C10 N1 -2.0(3) . . . . ?
C4 C8 C10 C24 175.2(2) . . . . ?
C4 C12 C16 O1 -179.3(2) . . . . ?
C4 C12 C16 N1 -0.5(3) . . . . ?
C6 C12 C16 O1 2.0(3) . . . . ?
C6 C12 C16 N1 -179.14(19) . . . . ?
C7 N4 C22 C14 -2.6(4) . . . . ?
C8 C1 C14 C22 -179.7(2) . . . . ?
C8 C1 C20 C7 178.8(2) . . . . ?
C8 C4 C12 C6 177.0(2) . . . . ?
C8 C4 C12 C16 -1.6(3) . . . . ?
C10 N1 C16 O1 -179.8(2) . . . . ?
C10 N1 C16 C12 1.3(3) . . . . ?
C12 C4 C8 C1 -178.9(2) . . . . ?
C12 C4 C8 C10 2.8(3) . . . . ?
C14 C1 C8 C4 -47.0(3) . . . . ?
C14 C1 C8 C10 131.2(2) . . . . ?
C14 C1 C20 C7 -3.7(3) . . . . ?
C16 N1 C10 C8 0.0(3) . . . . ?
C16 N1 C10 C24 -177.5(2) . . . . ?
C20 C1 C8 C4 130.4(2) . . . . ?
C20 C1 C8 C10 -51.5(3) . . . . ?
C20 C1 C14 C22 2.8(3) . . . . ?
C22 N4 C7 C20 1.6(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_ml_sesa_r
_database_code_depnum_ccdc_archive 'CCDC 2385549'
loop_
_audit_author_name
_audit_author_address
'kenguva gowtham'
;ICTIOCB
India
;
_audit_update_record             
;
2024-09-21 deposited with the CCDC.	2024-11-25 downloaded from the CCDC.
;
_audit_creation_date             2024-02-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H9 N3 O, C7 H6 O3'
_chemical_formula_sum            'C19 H15 N3 O4'
_chemical_formula_weight         349.34
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.0120(3)
_cell_length_b                   16.7621(7)
_cell_length_c                   12.6282(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.0102(3)
_cell_angle_gamma                90
_cell_volume                     1695.68(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4192
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      56
_cell_measurement_theta_min      3
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.977
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.854
_exptl_absorpt_correction_T_min  0.741
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1065
_diffrn_reflns_av_unetI/netI     0.0590
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            35954
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.493
_diffrn_reflns_theta_min         2.818
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEX4'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2403
_reflns_number_total             4192
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.091(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4192
_refine_ls_number_restraints     26
_refine_ls_R_factor_all          0.1065
_refine_ls_R_factor_gt           0.0514
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0679P)²+0.4292P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1286
_refine_ls_wR_factor_ref         0.1809
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O1-H1
 0.88 with sigma of 0.02
 O2-C15 \\sim O2A-C15
 with sigma of 0.02
 O2-C16 \\sim O2A-C16A
 with sigma of 0.02
 O3-C16 \\sim O3A-C16A
 with sigma of 0.02
 O3-C17 \\sim O3A-C17
 with sigma of 0.02
 O2-O3 \\sim O2A-O3A
 with sigma of 0.04
 C15-C16 \\sim C15-C16A
 with sigma of 0.04
 C16-C17 \\sim C16A-C17
 with sigma of 0.04
3. Rigid body (RIGU) restrains
 O3, O3A, C16A, C16, O2A, O2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(O3A)=Sof(C16A)=Sof(H16C)=Sof(H16D)=Sof(O2A)=1-FVAR(1)
 Sof(O2)=Sof(O3)=Sof(C16)=Sof(H16A)=Sof(H16B)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C16A(H16C,H16D)
5.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C9(H9), C10(H10), C11(H11), C12(H12), C14(H14), C18(H18), C19(H19)
5.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 -0.5639(2) -0.46333(11) -0.36301(15) 0.0841(6) Uani 1 1 d D . . . .
H1 H -0.640(4) -0.455(2) -0.417(2) 0.126 Uiso 1 1 d D U . . .
O2 O -0.324(2) -0.3277(11) -0.0638(12) 0.073(5) Uani 0.41(4) 1 d D . P A 1
O3 O -0.4620(19) -0.2118(8) -0.0965(12) 0.067(4) Uani 0.41(4) 1 d D . P A 1
O4 O -1.36630(19) -0.57275(10) -1.05890(13) 0.0696(5) Uani 1 1 d . . . . .
N1 N -1.0396(3) -0.72077(14) -1.06779(19) 0.0854(7) Uani 1 1 d . . . . .
N2 N -1.3023(2) -0.49022(11) -0.92163(15) 0.0581(5) Uani 1 1 d . . . . .
H2 H -1.394(3) -0.4640(14) -0.9350(19) 0.070 Uiso 1 1 d . U . . .
N3 N -0.7704(2) -0.46049(14) -0.53476(16) 0.0718(6) Uani 1 1 d . . . . .
C1 C -1.0792(3) -0.66671(14) -1.01810(19) 0.0618(6) Uani 1 1 d . . . . .
C2 C -1.1244(2) -0.59862(12) -0.95565(16) 0.0528(5) Uani 1 1 d . . . . .
C3 C -1.2710(2) -0.55579(13) -0.98498(16) 0.0541(5) Uani 1 1 d . . . . .
C4 C -1.2126(3) -0.46652(13) -0.83593(17) 0.0554(5) Uani 1 1 d . . . . .
C5 C -1.2823(3) -0.39543(15) -0.7799(2) 0.0735(7) Uani 1 1 d . . . . .
H5A H -1.237725 -0.347539 -0.809995 0.110 Uiso 1 1 calc R U . . .
H5B H -1.252197 -0.398014 -0.706052 0.110 Uiso 1 1 calc R U . . .
H5C H -1.401731 -0.395221 -0.787719 0.110 Uiso 1 1 calc R U . . .
C6 C -1.0731(2) -0.50930(12) -0.80717(16) 0.0524(5) Uani 1 1 d . . . . .
C7 C -1.0318(2) -0.57640(13) -0.86950(16) 0.0544(5) Uani 1 1 d . . . . .
H7 H -0.938021 -0.606297 -0.850803 0.065 Uiso 1 1 calc R U . . .
C8 C -0.9700(2) -0.49104(13) -0.71278(16) 0.0553(5) Uani 1 1 d . . . . .
C9 C -0.9224(3) -0.55148(15) -0.64419(17) 0.0615(6) Uani 1 1 d . . . . .
H9 H -0.957585 -0.603621 -0.656217 0.074 Uiso 1 1 calc R U . . .
C10 C -0.8228(3) -0.53354(16) -0.55838(18) 0.0688(6) Uani 1 1 d . . . . .
H10 H -0.789878 -0.575068 -0.513880 0.083 Uiso 1 1 calc R U . . .
C11 C -0.8161(3) -0.40256(17) -0.6003(2) 0.0752(7) Uani 1 1 d . . . . .
H11 H -0.780109 -0.350964 -0.585318 0.090 Uiso 1 1 calc R U . . .
C12 C -0.9135(3) -0.41458(15) -0.68908(19) 0.0690(6) Uani 1 1 d . . . . .
H12 H -0.941569 -0.371988 -0.733100 0.083 Uiso 1 1 calc R U . . .
C13 C -0.5474(3) -0.39757(14) -0.30156(17) 0.0595(6) Uani 1 1 d . . . . .
C14 C -0.4396(3) -0.40422(14) -0.21518(18) 0.0606(6) Uani 1 1 d . . . . .
H14 H -0.380388 -0.450911 -0.201381 0.073 Uiso 1 1 calc R U . . .
C15 C -0.4245(2) -0.33894(13) -0.15130(16) 0.0546(5) Uani 1 1 d D . . . .
C16 C -0.338(4) -0.2463(12) -0.034(2) 0.088(6) Uani 0.41(4) 1 d D . P A 1
H16A H -0.366660 -0.242459 0.040428 0.106 Uiso 0.41(4) 1 calc R U P A 1
H16B H -0.232657 -0.219049 -0.043754 0.106 Uiso 0.41(4) 1 calc R U P A 1
C17 C -0.5096(3) -0.26923(14) -0.16931(17) 0.0609(6) Uani 1 1 d D . . . .
C18 C -0.6141(3) -0.26173(15) -0.2540(2) 0.0718(7) Uani 1 1 d . . . . .
H18 H -0.670967 -0.214338 -0.267565 0.086 Uiso 1 1 calc R U . . .
C19 C -0.6333(3) -0.32756(15) -0.32010(18) 0.0662(6) Uani 1 1 d . . . . .
H19 H -0.705921 -0.324286 -0.378226 0.079 Uiso 1 1 calc R U . . .
O3A O -0.4734(17) -0.2161(6) -0.0889(9) 0.089(3) Uani 0.59(4) 1 d D . P A 2
C16A C -0.381(2) -0.2604(9) -0.0153(10) 0.076(3) Uani 0.59(4) 1 d D . P A 2
H16C H -0.448729 -0.271923 0.045693 0.091 Uiso 0.59(4) 1 calc R U P A 2
H16D H -0.284668 -0.229753 0.008676 0.091 Uiso 0.59(4) 1 calc R U P A 2
O2A O -0.3263(14) -0.3334(8) -0.0617(7) 0.067(3) Uani 0.59(4) 1 d D . P A 2


_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 H1 0.918(18) . ?
O1 C13 1.353(3) . ?
O2 C15 1.369(10) . ?
O2 C16 1.421(12) . ?
O3 C16 1.388(12) . ?
O3 C17 1.380(11) . ?
O4 C3 1.229(2) . ?
N1 C1 1.150(3) . ?
N2 H2 0.87(3) . ?
N2 C3 1.385(3) . ?
N2 C4 1.348(3) . ?
N3 C10 1.327(3) . ?
N3 C11 1.324(3) . ?
C1 C2 1.437(3) . ?
C2 C3 1.421(3) . ?
C2 C7 1.358(3) . ?
C4 C5 1.499(3) . ?
C4 C6 1.371(3) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.415(3) . ?
C6 C8 1.471(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.382(3) . ?
C8 C12 1.390(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.368(3) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.369(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.384(3) . ?
C13 C19 1.378(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.364(3) . ?
C15 C17 1.370(3) . ?
C15 O2A 1.370(8) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.353(3) . ?
C17 O3A 1.377(8) . ?
C18 H18 0.9300 . ?
C18 C19 1.390(3) . ?
C19 H19 0.9300 . ?
O3A C16A 1.393(9) . ?
C16A H16C 0.9700 . ?
C16A H16D 0.9700 . ?
C16A O2A 1.428(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 O1 H1 111(2) . . ?
C15 O2 C16 107.4(11) . . ?
C17 O3 C16 106.0(10) . . ?
C3 N2 H2 116.7(16) . . ?
C4 N2 H2 116.3(16) . . ?
C4 N2 C3 126.76(18) . . ?
C11 N3 C10 117.0(2) . . ?
N1 C1 C2 178.6(2) . . ?
C3 C2 C1 118.26(18) . . ?
C7 C2 C1 121.20(18) . . ?
C7 C2 C3 120.52(19) . . ?
O4 C3 N2 120.41(19) . . ?
O4 C3 C2 125.5(2) . . ?
N2 C3 C2 114.05(18) . . ?
N2 C4 C5 114.55(19) . . ?
N2 C4 C6 118.6(2) . . ?
C6 C4 C5 126.8(2) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 C7 117.76(18) . . ?
C4 C6 C8 123.32(19) . . ?
C7 C6 C8 118.85(18) . . ?
C2 C7 C6 122.25(19) . . ?
C2 C7 H7 118.9 . . ?
C6 C7 H7 118.9 . . ?
C9 C8 C6 120.0(2) . . ?
C9 C8 C12 117.1(2) . . ?
C12 C8 C6 122.9(2) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 C8 119.1(2) . . ?
C10 C9 H9 120.5 . . ?
N3 C10 C9 124.0(2) . . ?
N3 C10 H10 118.0 . . ?
C9 C10 H10 118.0 . . ?
N3 C11 H11 118.3 . . ?
N3 C11 C12 123.5(2) . . ?
C12 C11 H11 118.3 . . ?
C8 C12 H12 120.3 . . ?
C11 C12 C8 119.4(2) . . ?
C11 C12 H12 120.3 . . ?
O1 C13 C14 116.1(2) . . ?
O1 C13 C19 123.6(2) . . ?
C19 C13 C14 120.4(2) . . ?
C13 C14 H14 121.6 . . ?
C15 C14 C13 116.7(2) . . ?
C15 C14 H14 121.6 . . ?
O2 C15 C17 107.5(8) . . ?
C14 C15 O2 129.2(8) . . ?
C14 C15 C17 123.2(2) . . ?
C14 C15 O2A 125.9(5) . . ?
O2A C15 C17 110.9(5) . . ?
O2 C16 H16A 110.1 . . ?
O2 C16 H16B 110.1 . . ?
O3 C16 O2 107.9(11) . . ?
O3 C16 H16A 110.1 . . ?
O3 C16 H16B 110.1 . . ?
H16A C16 H16B 108.4 . . ?
C15 C17 O3 110.7(7) . . ?
C15 C17 O3A 109.3(5) . . ?
C18 C17 O3 128.4(7) . . ?
C18 C17 C15 120.7(2) . . ?
C18 C17 O3A 130.0(5) . . ?
C17 C18 H18 121.3 . . ?
C17 C18 C19 117.5(2) . . ?
C19 C18 H18 121.3 . . ?
C13 C19 C18 121.6(2) . . ?
C13 C19 H19 119.2 . . ?
C18 C19 H19 119.2 . . ?
C17 O3A C16A 104.5(7) . . ?
O3A C16A H16C 109.6 . . ?
O3A C16A H16D 109.6 . . ?
O3A C16A O2A 110.2(8) . . ?
H16C C16A H16D 108.1 . . ?
O2A C16A H16C 109.6 . . ?
O2A C16A H16D 109.6 . . ?
C15 O2A C16A 102.8(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C13 C14 C15 -178.7(2) . . . . ?
O1 C13 C19 C18 179.1(2) . . . . ?
O2 C15 C17 O3 1.8(12) . . . . ?
O2 C15 C17 C18 177.2(10) . . . . ?
O3 C17 C18 C19 175.6(9) . . . . ?
N2 C4 C6 C7 -0.2(3) . . . . ?
N2 C4 C6 C8 -177.35(19) . . . . ?
N3 C11 C12 C8 0.5(4) . . . . ?
C1 C2 C3 O4 1.5(3) . . . . ?
C1 C2 C3 N2 -178.65(19) . . . . ?
C1 C2 C7 C6 179.6(2) . . . . ?
C3 N2 C4 C5 -176.9(2) . . . . ?
C3 N2 C4 C6 1.4(3) . . . . ?
C3 C2 C7 C6 -1.8(3) . . . . ?
C4 N2 C3 O4 177.3(2) . . . . ?
C4 N2 C3 C2 -2.6(3) . . . . ?
C4 C6 C7 C2 0.4(3) . . . . ?
C4 C6 C8 C9 132.5(2) . . . . ?
C4 C6 C8 C12 -48.8(3) . . . . ?
C5 C4 C6 C7 178.0(2) . . . . ?
C5 C4 C6 C8 0.8(4) . . . . ?
C6 C8 C9 C10 178.28(19) . . . . ?
C6 C8 C12 C11 -179.1(2) . . . . ?
C7 C2 C3 O4 -177.2(2) . . . . ?
C7 C2 C3 N2 2.7(3) . . . . ?
C7 C6 C8 C9 -44.6(3) . . . . ?
C7 C6 C8 C12 134.1(2) . . . . ?
C8 C6 C7 C2 177.72(19) . . . . ?
C8 C9 C10 N3 1.4(4) . . . . ?
C9 C8 C12 C11 -0.4(3) . . . . ?
C10 N3 C11 C12 0.3(4) . . . . ?
C11 N3 C10 C9 -1.3(4) . . . . ?
C12 C8 C9 C10 -0.5(3) . . . . ?
C13 C14 C15 O2 -177.4(12) . . . . ?
C13 C14 C15 C17 -0.1(3) . . . . ?
C13 C14 C15 O2A 179.3(7) . . . . ?
C14 C13 C19 C18 0.5(4) . . . . ?
C14 C15 C17 O3 -176.0(8) . . . . ?
C14 C15 C17 C18 -0.6(4) . . . . ?
C14 C15 C17 O3A 177.4(7) . . . . ?
C14 C15 O2A C16A -169.1(9) . . . . ?
C15 O2 C16 O3 7(3) . . . . ?
C15 C17 C18 C19 1.1(4) . . . . ?
C15 C17 O3A C16A -7.5(11) . . . . ?
C16 O2 C15 C14 172.4(16) . . . . ?
C16 O2 C15 C17 -5(2) . . . . ?
C16 O3 C17 C15 2.4(18) . . . . ?
C16 O3 C17 C18 -172.6(16) . . . . ?
C17 O3 C16 O2 -6(3) . . . . ?
C17 C15 O2A C16A 10.3(12) . . . . ?
C17 C18 C19 C13 -1.1(4) . . . . ?
C17 O3A C16A O2A 14.2(15) . . . . ?
C18 C17 O3A C16A 170.2(8) . . . . ?
C19 C13 C14 C15 0.1(3) . . . . ?
O3A C17 C18 C19 -176.4(9) . . . . ?
O3A C16A O2A C15 -15.2(15) . . . . ?
O2A C15 C17 C18 180.0(6) . . . . ?
O2A C15 C17 O3A -2.0(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_mln_resv_0m
_database_code_depnum_ccdc_archive 'CCDC 2385550'
loop_
_audit_author_name
_audit_author_address
'kenguva gowtham'
;ICTIOCB
India
;
_audit_update_record             
;
2024-09-21 deposited with the CCDC.	2024-11-25 downloaded from the CCDC.
;
_audit_creation_date             2024-08-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H9 N3 O, C14 H12 O3, H2 O'
_chemical_formula_sum            'C26 H23 N3 O5'
_chemical_formula_weight         457.47
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.1866(13)
_cell_length_b                   14.7266(16)
_cell_length_c                   26.278(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.145(3)
_cell_angle_gamma                90
_cell_volume                     4656.0(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8201
_cell_measurement_temperature    298
_cell_measurement_theta_max      50
_cell_measurement_theta_min      3
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.845
_exptl_absorpt_correction_T_min  0.743
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1920
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1159
_diffrn_reflns_av_unetI/netI     0.0604
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            68168
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.412
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  
'Bruker D8 VENTURE diffractometer equipped with PHOTON II detector'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4311
_reflns_number_total             8201
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.976
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     632
_refine_ls_number_reflns         8201
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.1347
_refine_ls_R_factor_gt           0.0634
_refine_ls_restrained_S_all      0.975
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0981P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1572
_refine_ls_wR_factor_ref         0.1847
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Uiso/Uaniso restraints and constraints
N5 \\sim C51: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
within 2A
3. Rigid body (RIGU) restrains
 N5, C51
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Riding coordinates:
 O9(H9A,H9B)
4.b Free rotating group:
 O10(H10A,H10B)
4.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C16(H16), C36(H36), C48(H48), C49(H49), C2(H2A), C5(H5), C7(H7A),
 C9(H9), C11(H11), C13(H13), C17(H17), C22(H22), C25(H25), C27(H27), C28(H28),
 C29(H29), C35(H35), C41(H41), C43(H43), C45(H45), C46(H46), C47(H47), C3(H3A),
 C21(H21), C23(H23), C33(H33), C34(H34)
4.d Idealised Me refined as rotating group:
 C37(H37A,H37B,H37C), C39(H39A,H39B,H39C)
4.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3), O5(H5A), O6(H6), O7(H7), O8(H8)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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 0.40975(15) 0.65511(15) 0.83157(7) 0.0645(6) Uani 1 1 d . . . . .
N2 N 0.1392(2) 0.6295(2) 0.86039(10) 0.0757(8) Uani 1 1 d . . . . .
N4 N 0.3961(2) 0.65712(17) 0.74421(9) 0.0521(6) Uani 1 1 d . . . . .
H4 H 0.464(3) 0.664(2) 0.7481(11) 0.068(10) Uiso 1 1 d . . . . .
N6 N 0.0080(2) 0.63463(18) 0.54110(9) 0.0668(7) Uani 1 1 d . . . . .
C1 C 0.2269(2) 0.64672(18) 0.68672(10) 0.0467(7) Uani 1 1 d . . . . .
C4 C 0.1556(2) 0.64488(19) 0.63498(10) 0.0500(7) Uani 1 1 d . . . . .
C8 C 0.3499(2) 0.65155(19) 0.78806(10) 0.0507(7) Uani 1 1 d . . . . .
C10 C 0.2323(2) 0.64064(19) 0.77942(10) 0.0496(7) Uani 1 1 d . . . . .
C12 C 0.3412(2) 0.65630(19) 0.69466(10) 0.0501(7) Uani 1 1 d . . . . .
C14 C 0.1786(2) 0.6349(2) 0.82385(11) 0.0556(8) Uani 1 1 d . . . . .
C15 C 0.1851(3) 0.6037(2) 0.59163(11) 0.0640(8) Uani 1 1 d . . . . .
H15 H 0.255385 0.578453 0.592969 0.077 Uiso 1 1 calc R U . . .
C16 C 0.1753(2) 0.63839(19) 0.73015(10) 0.0525(7) Uani 1 1 d . . . . .
H16 H 0.098528 0.630966 0.725460 0.063 Uiso 1 1 calc R U . . .
C36 C 0.0494(2) 0.6823(2) 0.62918(11) 0.0588(8) Uani 1 1 d . . . . .
H36 H 0.025378 0.712092 0.656616 0.071 Uiso 1 1 calc R U . . .
C37 C 0.4141(3) 0.6679(2) 0.65509(11) 0.0695(9) Uani 1 1 d . . . . .
H37A H 0.437804 0.609432 0.644864 0.104 Uiso 1 1 calc R U . . .
H37B H 0.477991 0.703301 0.669112 0.104 Uiso 1 1 calc R U . . .
H37C H 0.373916 0.698524 0.625648 0.104 Uiso 1 1 calc R U . . .
C48 C -0.0200(3) 0.6749(2) 0.58237(11) 0.0648(9) Uani 1 1 d . . . . .
H48 H -0.090856 0.699722 0.579603 0.078 Uiso 1 1 calc R U . . .
C49 C 0.1096(3) 0.6004(2) 0.54642(12) 0.0702(9) Uani 1 1 d . . . . .
H49 H 0.131617 0.572352 0.517981 0.084 Uiso 1 1 calc R U . . .
H1 H 1.425(3) 0.337(2) 1.1532(13) 0.094(12) Uiso 1 1 d . . . . .
O2 O 0.03021(18) 0.40034(19) 0.68162(8) 0.0817(7) Uani 1 1 d . . . . .
H2 H 0.049895 0.401441 0.712942 0.123 Uiso 1 1 calc R U . . .
O3 O 0.2470(2) 0.29448(16) 0.83820(10) 0.0902(8) Uani 1 1 d . . . . .
H3 H 0.256884 0.239380 0.838811 0.135 Uiso 1 1 calc R U . . .
O5 O 0.4038(2) 0.56202(15) 0.92037(8) 0.0858(7) Uani 1 1 d . . . . .
H5A H 0.386807 0.587295 0.892428 0.129 Uiso 1 1 calc R U . . .
O6 O 0.85724(18) -0.00712(15) 1.13590(9) 0.0747(6) Uani 1 1 d . . . . .
H6 H 0.910383 0.023503 1.149148 0.112 Uiso 1 1 calc R U . . .
O7 O 0.18602(19) 0.3628(2) 0.52734(8) 0.0855(7) Uani 1 1 d . . . . .
H7 H 0.120170 0.361501 0.514471 0.128 Uiso 1 1 calc R U . . .
O8 O 0.91059(16) 0.41109(19) 0.83974(8) 0.0800(7) Uani 1 1 d . . . . .
H8 H 0.914481 0.406703 0.871086 0.120 Uiso 1 1 calc R U . . .
C2 C 0.2295(3) 0.3972(2) 0.68524(12) 0.0640(8) Uani 1 1 d . . . . .
H2A H 0.240131 0.403835 0.720885 0.077 Uiso 1 1 calc R U . . .
C5 C 0.4692(3) 0.3987(2) 0.73690(12) 0.0655(9) Uani 1 1 d . . . . .
H5 H 0.413885 0.399455 0.757567 0.079 Uiso 1 1 calc R U . . .
C7 C 0.4792(3) 0.4196(2) 0.94588(11) 0.0604(8) Uani 1 1 d . . . . .
H7A H 0.532002 0.449332 0.969536 0.073 Uiso 1 1 calc R U . . .
C9 C 0.5688(3) 0.1877(2) 0.98628(11) 0.0653(9) Uani 1 1 d . . . . .
H9 H 0.520490 0.152137 0.963606 0.078 Uiso 1 1 calc R U . . .
C11 C 0.6064(3) 0.4071(2) 0.81697(12) 0.0657(9) Uani 1 1 d . . . . .
H11 H 0.547484 0.409689 0.835481 0.079 Uiso 1 1 calc R U . . .
C13 C 0.1053(3) 0.3812(2) 0.60494(11) 0.0614(8) Uani 1 1 d . . . . .
H13 H 0.033473 0.377506 0.586726 0.074 Uiso 1 1 calc R U . . .
C17 C 0.3027(3) 0.3812(2) 0.60660(11) 0.0642(8) Uani 1 1 d . . . . .
H17 H 0.363122 0.378413 0.589051 0.077 Uiso 1 1 calc R U . . .
C19 C 0.1950(3) 0.3749(2) 0.57959(11) 0.0623(8) Uani 1 1 d . . . . .
C22 C 0.3991(2) 0.2827(2) 0.90783(10) 0.0590(8) Uani 1 1 d . . . . .
H22 H 0.395902 0.219609 0.906275 0.071 Uiso 1 1 calc R U . . .
C24 C 0.4020(3) 0.4698(2) 0.91338(10) 0.0586(8) Uani 1 1 d . . . . .
C25 C 0.7818(3) 0.3998(3) 0.76333(11) 0.0748(10) Uani 1 1 d . . . . .
H25 H 0.840896 0.397197 0.744904 0.090 Uiso 1 1 calc R U . . .
C27 C 0.3249(3) 0.4280(2) 0.87736(11) 0.0612(8) Uani 1 1 d . . . . .
H27 H 0.273695 0.462135 0.855205 0.073 Uiso 1 1 calc R U . . .
C28 C 0.5607(3) 0.2760(2) 0.98017(11) 0.0634(8) Uani 1 1 d . . . . .
H28 H 0.612742 0.310837 1.001412 0.076 Uiso 1 1 calc R U . . .
C29 C 0.7234(3) -0.0025(2) 1.06070(12) 0.0688(9) Uani 1 1 d . . . . .
H29 H 0.725954 -0.065513 1.058993 0.083 Uiso 1 1 calc R U . . .
C30 C 0.4792(2) 0.3259(2) 0.94379(10) 0.0534(7) Uani 1 1 d . . . . .
C31 C 0.1224(3) 0.3930(2) 0.65749(12) 0.0601(8) Uani 1 1 d . . . . .
C35 C 0.6528(3) 0.0457(2) 1.02444(12) 0.0677(9) Uani 1 1 d . . . . .
H35 H 0.607718 0.014283 0.998414 0.081 Uiso 1 1 calc R U . . .
C38 C 0.8017(2) 0.4062(2) 0.81692(11) 0.0597(8) Uani 1 1 d . . . . .
C40 C 0.3242(2) 0.3347(2) 0.87445(11) 0.0594(8) Uani 1 1 d . . . . .
C41 C 0.7887(3) 0.1367(2) 1.10157(12) 0.0684(9) Uani 1 1 d . . . . .
H41 H 0.835138 0.167796 1.127302 0.082 Uiso 1 1 calc R U . . .
C42 C 0.5842(2) 0.4014(2) 0.76405(11) 0.0562(8) Uani 1 1 d . . . . .
C43 C 0.6739(3) 0.3973(2) 0.73786(12) 0.0714(9) Uani 1 1 d . . . . .
H43 H 0.661120 0.392874 0.702105 0.086 Uiso 1 1 calc R U . . .
C44 C 0.7908(2) 0.0437(2) 1.09995(11) 0.0602(8) Uani 1 1 d . . . . .
C45 C 0.7172(3) 0.1843(2) 1.06474(12) 0.0723(9) Uani 1 1 d . . . . .
H45 H 0.715950 0.247351 1.066222 0.087 Uiso 1 1 calc R U . . .
C46 C 0.7153(3) 0.4092(2) 0.84366(12) 0.0644(8) Uani 1 1 d . . . . .
H46 H 0.728263 0.412631 0.879451 0.077 Uiso 1 1 calc R U . . .
C47 C 0.4352(3) 0.3953(2) 0.68723(12) 0.0661(9) Uani 1 1 d . . . . .
H47 H 0.490465 0.395346 0.666582 0.079 Uiso 1 1 calc R U . . .
C50 C 0.3196(3) 0.3915(2) 0.65985(11) 0.0593(8) Uani 1 1 d . . . . .
C52 C 0.6469(3) 0.1398(2) 1.02546(11) 0.0615(8) Uani 1 1 d . . . . .
O4 O 1.36608(16) 0.34716(15) 1.23280(7) 0.0628(6) Uani 1 1 d . . . . .
N1 N 1.3523(2) 0.34401(17) 1.14551(9) 0.0514(6) Uani 1 1 d . . . . .
N3 N 0.9781(2) 0.3991(2) 0.94109(10) 0.0727(8) Uani 1 1 d . . . . .
N5 N 1.0841(3) 0.3668(4) 1.25762(12) 0.1442(19) Uani 1 1 d . U . . .
C3 C 1.0801(3) 0.4331(2) 0.95023(12) 0.0749(10) Uani 1 1 d . . . . .
H3A H 1.105309 0.466076 0.924224 0.090 Uiso 1 1 calc R U . . .
C6 C 1.3057(2) 0.3508(2) 1.18961(10) 0.0518(7) Uani 1 1 d . . . . .
C18 C 1.2972(2) 0.3474(2) 1.09597(10) 0.0512(7) Uani 1 1 d . . . . .
C20 C 1.1847(2) 0.36331(19) 1.08816(10) 0.0495(7) Uani 1 1 d . . . . .
C21 C 0.9445(3) 0.3527(2) 0.97895(13) 0.0710(9) Uani 1 1 d . . . . .
H21 H 0.872969 0.328738 0.973285 0.085 Uiso 1 1 calc R U . . .
C23 C 1.1511(3) 0.4219(2) 0.99660(11) 0.0678(9) Uani 1 1 d . . . . .
H23 H 1.221866 0.447283 1.001167 0.081 Uiso 1 1 calc R U . . .
C26 C 1.1163(2) 0.3728(2) 1.03606(10) 0.0534(7) Uani 1 1 d . . . . .
C32 C 1.1882(2) 0.3611(2) 1.18042(10) 0.0569(8) Uani 1 1 d . . . . .
C33 C 1.0090(2) 0.3378(2) 1.02622(11) 0.0605(8) Uani 1 1 d . . . . .
H33 H 0.980926 0.304551 1.051370 0.073 Uiso 1 1 calc R U . . .
C34 C 1.1316(2) 0.3685(2) 1.13133(10) 0.0581(8) Uani 1 1 d . . . . .
H34 H 1.055077 0.377385 1.126560 0.070 Uiso 1 1 calc R U . . .
C39 C 1.3672(2) 0.3287(2) 1.05580(11) 0.0697(9) Uani 1 1 d . . . . .
H39A H 1.394762 0.384914 1.044284 0.105 Uiso 1 1 calc R U . . .
H39B H 1.323489 0.298340 1.027195 0.105 Uiso 1 1 calc R U . . .
H39C H 1.428613 0.290787 1.069935 0.105 Uiso 1 1 calc R U . . .
C51 C 1.1310(3) 0.3645(3) 1.22356(12) 0.0849(12) Uani 1 1 d . U . . .
O9 O 1.0840(2) 0.40558(19) 0.78277(8) 0.0975(8) Uani 1 1 d . . . . .
H9A H 1.020878 0.403801 0.805070 0.146 Uiso 1 1 d R U . . .
H9B H 1.136308 0.365221 0.795410 0.146 Uiso 1 1 d R U . . .
O10 O 0.3069(2) 0.12154(16) 0.83044(8) 0.0745(6) Uani 1 1 d G . . . .
H10A H 0.320571 0.116650 0.799840 0.112 Uiso 1 1 d G U . . .
H10B H 0.252110 0.086228 0.831439 0.112 Uiso 1 1 d G 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 C8 1.256(3) . ?
N2 C14 1.142(3) . ?
N4 H4 0.83(3) . ?
N4 C8 1.363(3) . ?
N4 C12 1.366(3) . ?
N6 C48 1.327(4) . ?
N6 C49 1.324(4) . ?
C1 C4 1.493(4) . ?
C1 C12 1.383(4) . ?
C1 C16 1.393(4) . ?
C4 C15 1.387(4) . ?
C4 C36 1.392(4) . ?
C8 C10 1.424(4) . ?
C10 C14 1.429(4) . ?
C10 C16 1.369(4) . ?
C12 C37 1.481(4) . ?
C15 H15 0.9300 . ?
C15 C49 1.383(4) . ?
C16 H16 0.9300 . ?
C36 H36 0.9300 . ?
C36 C48 1.382(4) . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C48 H48 0.9300 . ?
C49 H49 0.9300 . ?
O2 H2 0.8200 . ?
O2 C31 1.379(4) . ?
O3 H3 0.8200 . ?
O3 C40 1.363(3) . ?
O5 H5A 0.8200 . ?
O5 C24 1.370(4) . ?
O6 H6 0.8200 . ?
O6 C44 1.366(3) . ?
O7 H7 0.8200 . ?
O7 C19 1.371(3) . ?
O8 H8 0.8200 . ?
O8 C38 1.368(3) . ?
C2 H2A 0.9300 . ?
C2 C31 1.392(4) . ?
C2 C50 1.375(4) . ?
C5 H5 0.9300 . ?
C5 C42 1.469(4) . ?
C5 C47 1.306(4) . ?
C7 H7A 0.9300 . ?
C7 C24 1.381(4) . ?
C7 C30 1.381(4) . ?
C9 H9 0.9300 . ?
C9 C28 1.311(4) . ?
C9 C52 1.467(4) . ?
C11 H11 0.9300 . ?
C11 C42 1.376(4) . ?
C11 C46 1.399(4) . ?
C13 H13 0.9300 . ?
C13 C19 1.371(4) . ?
C13 C31 1.375(4) . ?
C17 H17 0.9300 . ?
C17 C19 1.392(4) . ?
C17 C50 1.390(4) . ?
C22 H22 0.9300 . ?
C22 C30 1.399(4) . ?
C22 C40 1.390(4) . ?
C24 C27 1.370(4) . ?
C25 H25 0.9300 . ?
C25 C38 1.394(4) . ?
C25 C43 1.378(4) . ?
C27 H27 0.9300 . ?
C27 C40 1.377(4) . ?
C28 H28 0.9300 . ?
C28 C30 1.462(4) . ?
C29 H29 0.9300 . ?
C29 C35 1.375(4) . ?
C29 C44 1.390(4) . ?
C35 H35 0.9300 . ?
C35 C52 1.388(4) . ?
C38 C46 1.357(4) . ?
C41 H41 0.9300 . ?
C41 C44 1.371(4) . ?
C41 C45 1.385(4) . ?
C42 C43 1.383(4) . ?
C43 H43 0.9300 . ?
C45 H45 0.9300 . ?
C45 C52 1.396(4) . ?
C46 H46 0.9300 . ?
C47 H47 0.9300 . ?
C47 C50 1.477(4) . ?
O4 C6 1.252(3) . ?
N1 H1 0.88(4) . ?
N1 C6 1.373(3) . ?
N1 C18 1.367(3) . ?
N3 C3 1.326(4) . ?
N3 C21 1.324(4) . ?
N5 C51 1.136(4) . ?
C3 H3A 0.9300 . ?
C3 C23 1.388(4) . ?
C6 C32 1.422(4) . ?
C18 C20 1.374(4) . ?
C18 C39 1.484(4) . ?
C20 C26 1.492(4) . ?
C20 C34 1.395(4) . ?
C21 H21 0.9300 . ?
C21 C33 1.378(4) . ?
C23 H23 0.9300 . ?
C23 C26 1.385(4) . ?
C26 C33 1.391(4) . ?
C32 C34 1.367(4) . ?
C32 C51 1.423(4) . ?
C33 H33 0.9300 . ?
C34 H34 0.9300 . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?
O9 H9A 1.0384 . ?
O9 H9B 0.8962 . ?
O10 H10A 0.8499 . ?
O10 H10B 0.8496 . ?

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
C8 N4 H4 116(2) . . ?
C8 N4 C12 126.9(3) . . ?
C12 N4 H4 117(2) . . ?
C49 N6 C48 116.2(3) . . ?
C12 C1 C4 124.5(2) . . ?
C12 C1 C16 117.4(2) . . ?
C16 C1 C4 118.1(2) . . ?
C15 C4 C1 124.5(3) . . ?
C15 C4 C36 116.1(3) . . ?
C36 C4 C1 119.3(2) . . ?
O1 C8 N4 120.6(3) . . ?
O1 C8 C10 125.0(2) . . ?
N4 C8 C10 114.3(3) . . ?
C8 C10 C14 117.2(2) . . ?
C16 C10 C8 120.1(2) . . ?
C16 C10 C14 122.7(2) . . ?
N4 C12 C1 118.2(2) . . ?
N4 C12 C37 114.3(2) . . ?
C1 C12 C37 127.5(2) . . ?
N2 C14 C10 177.5(3) . . ?
C4 C15 H15 120.1 . . ?
C49 C15 C4 119.8(3) . . ?
C49 C15 H15 120.1 . . ?
C1 C16 H16 118.5 . . ?
C10 C16 C1 123.0(3) . . ?
C10 C16 H16 118.5 . . ?
C4 C36 H36 120.2 . . ?
C48 C36 C4 119.5(3) . . ?
C48 C36 H36 120.2 . . ?
C12 C37 H37A 109.5 . . ?
C12 C37 H37B 109.5 . . ?
C12 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
N6 C48 C36 124.2(3) . . ?
N6 C48 H48 117.9 . . ?
C36 C48 H48 117.9 . . ?
N6 C49 C15 124.1(3) . . ?
N6 C49 H49 118.0 . . ?
C15 C49 H49 118.0 . . ?
C31 O2 H2 109.5 . . ?
C40 O3 H3 109.5 . . ?
C24 O5 H5A 109.5 . . ?
C44 O6 H6 109.5 . . ?
C19 O7 H7 109.5 . . ?
C38 O8 H8 109.5 . . ?
C31 C2 H2A 120.1 . . ?
C50 C2 H2A 120.1 . . ?
C50 C2 C31 119.9(3) . . ?
C42 C5 H5 116.1 . . ?
C47 C5 H5 116.1 . . ?
C47 C5 C42 127.8(3) . . ?
C24 C7 H7A 119.5 . . ?
C24 C7 C30 121.0(3) . . ?
C30 C7 H7A 119.5 . . ?
C28 C9 H9 116.9 . . ?
C28 C9 C52 126.2(3) . . ?
C52 C9 H9 116.9 . . ?
C42 C11 H11 119.1 . . ?
C42 C11 C46 121.8(3) . . ?
C46 C11 H11 119.1 . . ?
C19 C13 H13 120.3 . . ?
C19 C13 C31 119.4(3) . . ?
C31 C13 H13 120.3 . . ?
C19 C17 H17 120.1 . . ?
C50 C17 H17 120.1 . . ?
C50 C17 C19 119.9(3) . . ?
O7 C19 C17 116.0(3) . . ?
C13 C19 O7 123.5(3) . . ?
C13 C19 C17 120.5(3) . . ?
C30 C22 H22 120.2 . . ?
C40 C22 H22 120.2 . . ?
C40 C22 C30 119.5(3) . . ?
O5 C24 C7 116.9(3) . . ?
C27 C24 O5 122.2(3) . . ?
C27 C24 C7 120.8(3) . . ?
C38 C25 H25 120.3 . . ?
C43 C25 H25 120.3 . . ?
C43 C25 C38 119.5(3) . . ?
C24 C27 H27 120.5 . . ?
C24 C27 C40 119.0(3) . . ?
C40 C27 H27 120.5 . . ?
C9 C28 H28 116.3 . . ?
C9 C28 C30 127.5(3) . . ?
C30 C28 H28 116.3 . . ?
C35 C29 H29 120.3 . . ?
C35 C29 C44 119.5(3) . . ?
C44 C29 H29 120.3 . . ?
C7 C30 C22 118.5(3) . . ?
C7 C30 C28 118.7(3) . . ?
C22 C30 C28 122.8(3) . . ?
O2 C31 C2 121.4(3) . . ?
C13 C31 O2 117.9(3) . . ?
C13 C31 C2 120.8(3) . . ?
C29 C35 H35 119.0 . . ?
C29 C35 C52 122.1(3) . . ?
C52 C35 H35 119.0 . . ?
O8 C38 C25 116.6(3) . . ?
C46 C38 O8 123.4(3) . . ?
C46 C38 C25 120.0(3) . . ?
O3 C40 C22 120.8(3) . . ?
O3 C40 C27 118.0(3) . . ?
C27 C40 C22 121.2(3) . . ?
C44 C41 H41 120.1 . . ?
C44 C41 C45 119.7(3) . . ?
C45 C41 H41 120.1 . . ?
C11 C42 C5 120.8(3) . . ?
C11 C42 C43 117.4(3) . . ?
C43 C42 C5 121.8(3) . . ?
C25 C43 C42 121.8(3) . . ?
C25 C43 H43 119.1 . . ?
C42 C43 H43 119.1 . . ?
O6 C44 C29 117.4(3) . . ?
O6 C44 C41 122.6(3) . . ?
C41 C44 C29 120.0(3) . . ?
C41 C45 H45 119.2 . . ?
C41 C45 C52 121.6(3) . . ?
C52 C45 H45 119.2 . . ?
C11 C46 H46 120.3 . . ?
C38 C46 C11 119.5(3) . . ?
C38 C46 H46 120.3 . . ?
C5 C47 H47 116.0 . . ?
C5 C47 C50 127.9(3) . . ?
C50 C47 H47 116.0 . . ?
C2 C50 C17 119.5(3) . . ?
C2 C50 C47 122.3(3) . . ?
C17 C50 C47 118.2(3) . . ?
C35 C52 C9 119.8(3) . . ?
C35 C52 C45 117.1(3) . . ?
C45 C52 C9 123.1(3) . . ?
C6 N1 H1 110(2) . . ?
C18 N1 H1 123(2) . . ?
C18 N1 C6 126.5(3) . . ?
C21 N3 C3 116.8(3) . . ?
N3 C3 H3A 118.3 . . ?
N3 C3 C23 123.4(3) . . ?
C23 C3 H3A 118.3 . . ?
O4 C6 N1 120.0(3) . . ?
O4 C6 C32 126.1(3) . . ?
N1 C6 C32 113.9(2) . . ?
N1 C18 C20 118.4(2) . . ?
N1 C18 C39 114.8(2) . . ?
C20 C18 C39 126.7(2) . . ?
C18 C20 C26 123.5(2) . . ?
C18 C20 C34 118.0(2) . . ?
C34 C20 C26 118.5(2) . . ?
N3 C21 H21 118.0 . . ?
N3 C21 C33 124.0(3) . . ?
C33 C21 H21 118.0 . . ?
C3 C23 H23 120.1 . . ?
C26 C23 C3 119.8(3) . . ?
C26 C23 H23 120.1 . . ?
C23 C26 C20 122.8(3) . . ?
C23 C26 C33 116.4(3) . . ?
C33 C26 C20 120.5(3) . . ?
C6 C32 C51 118.4(3) . . ?
C34 C32 C6 120.8(3) . . ?
C34 C32 C51 120.7(3) . . ?
C21 C33 C26 119.6(3) . . ?
C21 C33 H33 120.2 . . ?
C26 C33 H33 120.2 . . ?
C20 C34 H34 118.9 . . ?
C32 C34 C20 122.2(3) . . ?
C32 C34 H34 118.9 . . ?
C18 C39 H39A 109.5 . . ?
C18 C39 H39B 109.5 . . ?
C18 C39 H39C 109.5 . . ?
H39A C39 H39B 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
N5 C51 C32 179.1(4) . . ?
H9A O9 H9B 108.7 . . ?
H10A O10 H10B 104.5 . . ?

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
O1 C8 C10 C14 1.1(4) . . . . ?
O1 C8 C10 C16 179.5(3) . . . . ?
N4 C8 C10 C14 -179.6(3) . . . . ?
N4 C8 C10 C16 -1.3(4) . . . . ?
C1 C4 C15 C49 175.4(3) . . . . ?
C1 C4 C36 C48 -175.3(3) . . . . ?
C4 C1 C12 N4 179.8(2) . . . . ?
C4 C1 C12 C37 1.1(5) . . . . ?
C4 C1 C16 C10 -178.9(3) . . . . ?
C4 C15 C49 N6 0.0(5) . . . . ?
C4 C36 C48 N6 -0.9(5) . . . . ?
C8 N4 C12 C1 -1.7(4) . . . . ?
C8 N4 C12 C37 177.2(3) . . . . ?
C8 C10 C16 C1 -0.2(4) . . . . ?
C12 N4 C8 O1 -178.4(3) . . . . ?
C12 N4 C8 C10 2.3(4) . . . . ?
C12 C1 C4 C15 37.6(4) . . . . ?
C12 C1 C4 C36 -146.0(3) . . . . ?
C12 C1 C16 C10 1.0(4) . . . . ?
C14 C10 C16 C1 178.0(3) . . . . ?
C15 C4 C36 C48 1.5(4) . . . . ?
C16 C1 C4 C15 -142.5(3) . . . . ?
C16 C1 C4 C36 33.9(4) . . . . ?
C16 C1 C12 N4 -0.1(4) . . . . ?
C16 C1 C12 C37 -178.8(3) . . . . ?
C36 C4 C15 C49 -1.1(4) . . . . ?
C48 N6 C49 C15 0.7(5) . . . . ?
C49 N6 C48 C36 -0.2(5) . . . . ?
O5 C24 C27 C40 -176.4(3) . . . . ?
O8 C38 C46 C11 177.7(3) . . . . ?
C5 C42 C43 C25 -180.0(3) . . . . ?
C5 C47 C50 C2 4.5(5) . . . . ?
C5 C47 C50 C17 -175.1(3) . . . . ?
C7 C24 C27 C40 1.0(5) . . . . ?
C9 C28 C30 C7 175.2(3) . . . . ?
C9 C28 C30 C22 -3.0(5) . . . . ?
C11 C42 C43 C25 -0.6(5) . . . . ?
C19 C13 C31 O2 179.1(3) . . . . ?
C19 C13 C31 C2 -1.0(5) . . . . ?
C19 C17 C50 C2 -1.2(5) . . . . ?
C19 C17 C50 C47 178.4(3) . . . . ?
C24 C7 C30 C22 0.1(4) . . . . ?
C24 C7 C30 C28 -178.1(3) . . . . ?
C24 C27 C40 O3 -179.8(3) . . . . ?
C24 C27 C40 C22 1.0(5) . . . . ?
C25 C38 C46 C11 -0.9(5) . . . . ?
C28 C9 C52 C35 -174.2(3) . . . . ?
C28 C9 C52 C45 5.9(5) . . . . ?
C29 C35 C52 C9 -179.0(3) . . . . ?
C29 C35 C52 C45 0.9(5) . . . . ?
C30 C7 C24 O5 176.0(3) . . . . ?
C30 C7 C24 C27 -1.5(5) . . . . ?
C30 C22 C40 O3 178.4(3) . . . . ?
C30 C22 C40 C27 -2.4(4) . . . . ?
C31 C2 C50 C17 -0.3(5) . . . . ?
C31 C2 C50 C47 -179.9(3) . . . . ?
C31 C13 C19 O7 179.7(3) . . . . ?
C31 C13 C19 C17 -0.5(5) . . . . ?
C35 C29 C44 O6 178.2(3) . . . . ?
C35 C29 C44 C41 -1.6(5) . . . . ?
C38 C25 C43 C42 0.2(5) . . . . ?
C40 C22 C30 C7 1.8(4) . . . . ?
C40 C22 C30 C28 180.0(3) . . . . ?
C41 C45 C52 C9 179.0(3) . . . . ?
C41 C45 C52 C35 -0.9(5) . . . . ?
C42 C5 C47 C50 179.2(3) . . . . ?
C42 C11 C46 C38 0.5(5) . . . . ?
C43 C25 C38 O8 -178.1(3) . . . . ?
C43 C25 C38 C46 0.6(5) . . . . ?
C44 C29 C35 C52 0.3(5) . . . . ?
C44 C41 C45 C52 -0.3(5) . . . . ?
C45 C41 C44 O6 -178.2(3) . . . . ?
C45 C41 C44 C29 1.6(5) . . . . ?
C46 C11 C42 C5 179.6(3) . . . . ?
C46 C11 C42 C43 0.2(5) . . . . ?
C47 C5 C42 C11 178.3(3) . . . . ?
C47 C5 C42 C43 -2.3(5) . . . . ?
C50 C2 C31 O2 -178.7(3) . . . . ?
C50 C2 C31 C13 1.4(5) . . . . ?
C50 C17 C19 O7 -178.6(3) . . . . ?
C50 C17 C19 C13 1.6(5) . . . . ?
C52 C9 C28 C30 -175.6(3) . . . . ?
O4 C6 C32 C34 176.9(3) . . . . ?
O4 C6 C32 C51 -2.3(5) . . . . ?
N1 C6 C32 C34 -3.7(4) . . . . ?
N1 C6 C32 C51 177.1(3) . . . . ?
N1 C18 C20 C26 177.1(3) . . . . ?
N1 C18 C20 C34 -4.6(4) . . . . ?
N3 C3 C23 C26 0.3(5) . . . . ?
N3 C21 C33 C26 0.1(5) . . . . ?
C3 N3 C21 C33 -0.4(5) . . . . ?
C3 C23 C26 C20 -175.6(3) . . . . ?
C3 C23 C26 C33 -0.6(5) . . . . ?
C6 N1 C18 C20 3.2(5) . . . . ?
C6 N1 C18 C39 -174.0(3) . . . . ?
C6 C32 C34 C20 2.3(5) . . . . ?
C18 N1 C6 O4 -179.6(3) . . . . ?
C18 N1 C6 C32 1.0(4) . . . . ?
C18 C20 C26 C23 -42.6(4) . . . . ?
C18 C20 C26 C33 142.6(3) . . . . ?
C18 C20 C34 C32 2.0(5) . . . . ?
C20 C26 C33 C21 175.5(3) . . . . ?
C21 N3 C3 C23 0.2(5) . . . . ?
C23 C26 C33 C21 0.4(4) . . . . ?
C26 C20 C34 C32 -179.6(3) . . . . ?
C34 C20 C26 C23 139.1(3) . . . . ?
C34 C20 C26 C33 -35.7(4) . . . . ?
C39 C18 C20 C26 -6.0(5) . . . . ?
C39 C18 C20 C34 172.3(3) . . . . ?
C51 C32 C34 C20 -178.5(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
