# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_Ibu_az
_database_code_depnum_ccdc_archive 'CCDC 2049306'
loop_
_audit_author_name
_audit_author_address
'Sabir Ahmed'
;Research fellow
India
;
_audit_update_record             
;
2020-12-09 deposited with the CCDC.	2026-03-27 downloaded from the CCDC.
;
_audit_creation_date             2020-12-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H18 N4 O'
_chemical_formula_sum            'C13 H18 N4 O'
_chemical_formula_weight         246.31
_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      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                   5.207(2)
_cell_length_b                   11.084(6)
_cell_length_c                   11.850(5)
_cell_angle_alpha                98.187(17)
_cell_angle_beta                 97.794(15)
_cell_angle_gamma                95.548(17)
_cell_volume                     665.9(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1772
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      23.61
_cell_measurement_theta_min      2.35
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.7450
_exptl_absorpt_correction_T_min  0.4870
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1574 before and 0.0994 after correction. The Ratio of minimum to maximum transmission is 0.6537. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0910
_diffrn_reflns_av_unetI/netI     0.1027
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5569
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        23.661
_diffrn_reflns_theta_max         23.661
_diffrn_reflns_theta_min         2.355
_diffrn_ambient_temperature      110.46
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1457
_reflns_number_total             1995
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         1995
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0899
_refine_ls_R_factor_gt           0.0647
_refine_ls_restrained_S_all      1.036
_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)+(0.0834P)²+0.2062P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1646
_refine_ls_wR_factor_ref         0.1825
_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
2.a Ternary CH refined with riding coordinates:
 C11(H11), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C6(H6), C5(H5), C3(H3)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.6001(4) 0.14158(19) 0.09791(17) 0.0251(6) Uani 1 1 d . . . . .
N1 N 0.1739(4) 0.1759(2) 0.0805(2) 0.0220(6) Uani 1 1 d . . . . .
H1 H 0.013682 0.143790 0.082696 0.026 Uiso 1 1 calc R . . . .
N2 N 0.2812(5) 0.0020(2) 0.1450(2) 0.0241(7) Uani 1 1 d . . . . .
N3 N 0.4638(5) -0.0613(2) 0.1650(2) 0.0253(7) Uani 1 1 d . . . . .
C13 C 0.3717(6) 0.1123(3) 0.1058(2) 0.0205(7) Uani 1 1 d . . . . .
N4 N 0.6114(6) -0.1249(3) 0.1861(2) 0.0349(8) Uani 1 1 d . . . . .
C11 C 0.2170(5) 0.2985(3) 0.0490(3) 0.0218(7) Uani 1 1 d . . . . .
H11 H 0.376826 0.301993 0.010734 0.026 Uiso 1 1 calc R . . . .
C1 C 0.2660(5) 0.3972(3) 0.1540(2) 0.0223(7) Uani 1 1 d . . . . .
C4 C 0.3606(6) 0.5803(3) 0.3517(3) 0.0287(8) Uani 1 1 d . . . . .
C12 C -0.0130(6) 0.3159(3) -0.0393(3) 0.0270(8) Uani 1 1 d . . . . .
H12A H -0.029591 0.251868 -0.106953 0.041 Uiso 1 1 calc GR . . . .
H12B H 0.016464 0.396715 -0.062802 0.041 Uiso 1 1 calc GR . . . .
H12C H -0.173756 0.310136 -0.004878 0.041 Uiso 1 1 calc GR . . . .
C2 C 0.4744(6) 0.4892(3) 0.1705(3) 0.0279(8) Uani 1 1 d . . . . .
H2 H 0.588836 0.490437 0.114588 0.033 Uiso 1 1 calc R . . . .
C6 C 0.1022(6) 0.4001(3) 0.2375(3) 0.0273(8) Uani 1 1 d . . . . .
H6 H -0.044795 0.339722 0.227836 0.033 Uiso 1 1 calc R . . . .
C5 C 0.1492(6) 0.4890(3) 0.3341(3) 0.0307(8) Uani 1 1 d . . . . .
H5 H 0.034717 0.488056 0.390025 0.037 Uiso 1 1 calc R . . . .
C8 C 0.2071(6) 0.7538(3) 0.4839(3) 0.0308(8) Uani 1 1 d . . . . .
H8 H 0.042465 0.699027 0.483155 0.037 Uiso 1 1 calc R . . . .
C3 C 0.5185(6) 0.5792(3) 0.2673(3) 0.0329(9) Uani 1 1 d . . . . .
H3 H 0.661105 0.641738 0.275639 0.039 Uiso 1 1 calc R . . . .
C7 C 0.4196(6) 0.6734(3) 0.4608(3) 0.0375(9) Uani 1 1 d . . . . .
H7A H 0.580752 0.727206 0.457388 0.045 Uiso 1 1 calc R . . . .
H7B H 0.456073 0.629121 0.526967 0.045 Uiso 1 1 calc R . . . .
C9 C 0.1560(8) 0.8348(4) 0.3934(3) 0.0447(10) Uani 1 1 d . . . . .
H9A H 0.312311 0.892384 0.395330 0.067 Uiso 1 1 calc GR . . . .
H9B H 0.009700 0.880765 0.408996 0.067 Uiso 1 1 calc GR . . . .
H9C H 0.112860 0.783970 0.317165 0.067 Uiso 1 1 calc GR . . . .
C10 C 0.2780(8) 0.8322(4) 0.6034(3) 0.0473(10) Uani 1 1 d . . . . .
H10A H 0.310725 0.778808 0.661637 0.071 Uiso 1 1 calc GR . . . .
H10B H 0.133392 0.878975 0.619851 0.071 Uiso 1 1 calc GR . . . .
H10C H 0.435372 0.889066 0.605109 0.071 Uiso 1 1 calc GR . . . .


_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 C13 1.222(3) . ?
N1 H1 0.8800 . ?
N1 C13 1.329(4) . ?
N1 C11 1.464(4) . ?
N2 N3 1.252(4) . ?
N2 C13 1.429(4) . ?
N3 N4 1.119(3) . ?
C11 H11 1.0000 . ?
C11 C1 1.511(4) . ?
C11 C12 1.526(4) . ?
C1 C2 1.388(4) . ?
C1 C6 1.391(4) . ?
C4 C5 1.394(5) . ?
C4 C3 1.377(5) . ?
C4 C7 1.510(5) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C2 H2 0.9500 . ?
C2 C3 1.387(5) . ?
C6 H6 0.9500 . ?
C6 C5 1.377(4) . ?
C5 H5 0.9500 . ?
C8 H8 1.0000 . ?
C8 C7 1.515(5) . ?
C8 C9 1.506(5) . ?
C8 C10 1.530(5) . ?
C3 H3 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 N1 H1 119.3 . . ?
C13 N1 C11 121.3(2) . . ?
C11 N1 H1 119.3 . . ?
N3 N2 C13 111.1(2) . . ?
N4 N3 N2 173.8(3) . . ?
O1 C13 N1 126.1(3) . . ?
O1 C13 N2 123.5(3) . . ?
N1 C13 N2 110.3(2) . . ?
N1 C11 H11 107.7 . . ?
N1 C11 C1 111.6(2) . . ?
N1 C11 C12 108.8(2) . . ?
C1 C11 H11 107.7 . . ?
C1 C11 C12 113.2(2) . . ?
C12 C11 H11 107.7 . . ?
C2 C1 C11 121.5(3) . . ?
C2 C1 C6 117.3(3) . . ?
C6 C1 C11 121.2(3) . . ?
C5 C4 C7 121.3(3) . . ?
C3 C4 C5 117.1(3) . . ?
C3 C4 C7 121.5(3) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.1(3) . . ?
C3 C2 H2 119.4 . . ?
C1 C6 H6 119.4 . . ?
C5 C6 C1 121.2(3) . . ?
C5 C6 H6 119.4 . . ?
C4 C5 H5 119.2 . . ?
C6 C5 C4 121.6(3) . . ?
C6 C5 H5 119.2 . . ?
C7 C8 H8 108.0 . . ?
C7 C8 C10 110.2(3) . . ?
C9 C8 H8 108.0 . . ?
C9 C8 C7 112.4(3) . . ?
C9 C8 C10 110.0(3) . . ?
C10 C8 H8 108.0 . . ?
C4 C3 C2 121.6(3) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C4 C7 C8 115.8(2) . . ?
C4 C7 H7A 108.3 . . ?
C4 C7 H7B 108.3 . . ?
C8 C7 H7A 108.3 . . ?
C8 C7 H7B 108.3 . . ?
H7A C7 H7B 107.4 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
#
_vrf_THETM01_Ibu_az              
;
PROBLEM:  The value of sine(theta_max)/wavelength is less than 0.575
            Calculated sin(theta_max)/wavelength =    0.5647
RESPONSE: The crystal was poorly diffracting and did not diffracted at
higher bragg angles. The data quality did not improved with 
multiple data collection.
;
# end Validation reply form
####################################################################### 
# 
# 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_mo_pd070324_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2362781'
loop_
_audit_author_name
_audit_author_address
'Manoj Kumar Baskey'
;Indian Association for the Cultivation of Science
India
;
_audit_update_record             
;
2024-06-14 deposited with the CCDC.	2026-03-27 downloaded from the CCDC.
;
_audit_creation_date             2024-06-14
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        Diclo-Az
_chemical_formula_moiety         'C14 H11 Cl2 N5 O'
_chemical_formula_sum            'C14 H11 Cl2 N5 O'
_chemical_formula_weight         336.18
_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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   14.073(9)
_cell_length_b                   4.879(3)
_cell_length_c                   22.444(14)
_cell_angle_alpha                90
_cell_angle_beta                 98.92(2)
_cell_angle_gamma                90
_cell_volume                     1522.2(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4374
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      25.04
_cell_measurement_theta_min      2.52
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.950
_exptl_absorpt_coefficient_mu    0.435
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.4729
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1499 before and 0.1154 after correction.
The Ratio of minimum to maximum transmission is 0.6346.
The λ/2 correction factor is Not present.
;
_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    1.467
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0957
_diffrn_reflns_av_unetI/netI     0.0773
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            12467
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.091
_diffrn_reflns_theta_max         25.091
_diffrn_reflns_theta_min         2.930
_diffrn_ambient_temperature      150.0
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2030
_reflns_number_total             2695
_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       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2695
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0822
_refine_ls_R_factor_gt           0.0624
_refine_ls_restrained_S_all      1.031
_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)+(0.0897P)²+0.8429P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1568
_refine_ls_wR_factor_ref         0.1731
_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
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C11(H11), C8(H8), C10(H10), C9(H9), C4(H4), C3(H3), C2(H2A)
;
_atom_sites_solution_hydrogens   geom
_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
Cl1 Cl 0.32550(7) 0.14145(19) 0.27634(4) 0.0554(3) Uani 1 1 d . . . . .
Cl2 Cl 0.36117(8) 0.7165(2) 0.48440(5) 0.0685(4) Uani 1 1 d . . . . .
O1 O 0.15741(17) -0.2136(4) 0.53791(10) 0.0397(6) Uani 1 1 d . . . . .
N2 N 0.15207(19) 0.2204(5) 0.50134(11) 0.0330(6) Uani 1 1 d . . . . .
H2 H 0.169982 0.391778 0.508227 0.040 Uiso 1 1 calc R U . . .
N1 N 0.26429(18) 0.3176(5) 0.39370(13) 0.0375(7) Uani 1 1 d . . . . .
H1 H 0.265800 0.167575 0.415588 0.045 Uiso 1 1 calc R U . . .
N3 N 0.2217(2) 0.1458(6) 0.59934(13) 0.0442(7) Uani 1 1 d . . . . .
N4 N 0.2397(2) -0.0349(7) 0.63925(14) 0.0520(8) Uani 1 1 d . . . . .
C12 C 0.0926(2) 0.3647(6) 0.39621(13) 0.0297(7) Uani 1 1 d . . . . .
C14 C 0.1742(2) 0.0305(6) 0.54387(13) 0.0306(7) Uani 1 1 d . . . . .
C11 C 0.0054(2) 0.4895(7) 0.37485(14) 0.0357(7) Uani 1 1 d . . . . .
H11 H -0.050314 0.439064 0.391360 0.043 Uiso 1 1 calc R U . . .
C7 C 0.1749(2) 0.4432(6) 0.37205(13) 0.0301(7) Uani 1 1 d . . . . .
C8 C 0.1671(2) 0.6404(6) 0.32677(14) 0.0361(8) Uani 1 1 d . . . . .
H8 H 0.222345 0.692744 0.310025 0.043 Uiso 1 1 calc R U . . .
C6 C 0.3518(2) 0.4318(6) 0.38039(15) 0.0362(7) Uani 1 1 d . . . . .
C13 C 0.0976(2) 0.1405(6) 0.44307(14) 0.0330(7) Uani 1 1 d . . . . .
H13A H 0.031425 0.090129 0.448691 0.040 Uiso 1 1 calc R U . . .
H13B H 0.127894 -0.023590 0.428108 0.040 Uiso 1 1 calc R U . . .
C10 C -0.0020(3) 0.6876(7) 0.32956(15) 0.0409(8) Uani 1 1 d . . . . .
H10 H -0.062264 0.770719 0.315230 0.049 Uiso 1 1 calc R U . . .
C5 C 0.3893(2) 0.3622(6) 0.32833(16) 0.0395(8) Uani 1 1 d . . . . .
C9 C 0.0785(3) 0.7616(7) 0.30587(15) 0.0416(8) Uani 1 1 d . . . . .
H9 H 0.073858 0.896400 0.275006 0.050 Uiso 1 1 calc R U . . .
C4 C 0.4761(3) 0.4657(7) 0.31631(18) 0.0510(9) Uani 1 1 d . . . . .
H4 H 0.499694 0.415258 0.280420 0.061 Uiso 1 1 calc R U . . .
C3 C 0.5275(3) 0.6412(9) 0.3566(2) 0.0632(12) Uani 1 1 d . . . . .
H3 H 0.587559 0.709891 0.348974 0.076 Uiso 1 1 calc R U . . .
C1 C 0.4055(3) 0.6167(7) 0.41952(17) 0.0475(9) Uani 1 1 d . . . . .
N5 N 0.2580(3) -0.1772(8) 0.67761(19) 0.0865(14) Uani 1 1 d . . . . .
C2 C 0.4932(3) 0.7187(9) 0.4079(2) 0.0633(12) Uani 1 1 d . . . . .
H2A H 0.529071 0.841783 0.435506 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
Cl1 C5 1.733(4) . ?
Cl2 C1 1.740(4) . ?
O1 C14 1.218(4) . ?
N2 H2 0.8800 . ?
N2 C14 1.332(4) . ?
N2 C13 1.463(4) . ?
N1 H1 0.8800 . ?
N1 C7 1.415(4) . ?
N1 C6 1.425(4) . ?
N3 N4 1.254(4) . ?
N3 C14 1.434(4) . ?
N4 N5 1.105(5) . ?
C12 C11 1.387(4) . ?
C12 C7 1.406(4) . ?
C12 C13 1.511(4) . ?
C11 H11 0.9500 . ?
C11 C10 1.395(5) . ?
C7 C8 1.391(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.393(5) . ?
C6 C5 1.396(5) . ?
C6 C1 1.396(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C10 H10 0.9500 . ?
C10 C9 1.372(5) . ?
C5 C4 1.387(5) . ?
C9 H9 0.9500 . ?
C4 H4 0.9500 . ?
C4 C3 1.368(6) . ?
C3 H3 0.9500 . ?
C3 C2 1.368(6) . ?
C1 C2 1.391(5) . ?
C2 H2A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 N2 H2 120.4 . . ?
C14 N2 C13 119.2(2) . . ?
C13 N2 H2 120.4 . . ?
C7 N1 H1 119.7 . . ?
C7 N1 C6 120.6(3) . . ?
C6 N1 H1 119.7 . . ?
N4 N3 C14 111.1(3) . . ?
N5 N4 N3 174.2(4) . . ?
C11 C12 C7 119.0(3) . . ?
C11 C12 C13 120.1(3) . . ?
C7 C12 C13 120.9(3) . . ?
O1 C14 N2 125.6(3) . . ?
O1 C14 N3 122.4(3) . . ?
N2 C14 N3 112.0(3) . . ?
C12 C11 H11 119.4 . . ?
C12 C11 C10 121.2(3) . . ?
C10 C11 H11 119.4 . . ?
C12 C7 N1 119.4(3) . . ?
C8 C7 N1 121.1(3) . . ?
C8 C7 C12 119.5(3) . . ?
C7 C8 H8 119.8 . . ?
C7 C8 C9 120.4(3) . . ?
C9 C8 H8 119.8 . . ?
C5 C6 N1 122.1(3) . . ?
C5 C6 C1 116.5(3) . . ?
C1 C6 N1 121.4(3) . . ?
N2 C13 C12 113.0(2) . . ?
N2 C13 H13A 109.0 . . ?
N2 C13 H13B 109.0 . . ?
C12 C13 H13A 109.0 . . ?
C12 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C11 C10 H10 120.3 . . ?
C9 C10 C11 119.5(3) . . ?
C9 C10 H10 120.3 . . ?
C6 C5 Cl1 119.5(2) . . ?
C4 C5 Cl1 118.4(3) . . ?
C4 C5 C6 122.2(3) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.5(3) . . ?
C10 C9 H9 119.8 . . ?
C5 C4 H4 120.3 . . ?
C3 C4 C5 119.4(4) . . ?
C3 C4 H4 120.3 . . ?
C4 C3 H3 119.7 . . ?
C4 C3 C2 120.7(4) . . ?
C2 C3 H3 119.7 . . ?
C6 C1 Cl2 118.5(3) . . ?
C2 C1 Cl2 120.0(3) . . ?
C2 C1 C6 121.5(4) . . ?
C3 C2 C1 119.8(4) . . ?
C3 C2 H2A 120.1 . . ?
C1 C2 H2A 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C5 C4 C3 179.8(3) . . . . ?
Cl2 C1 C2 C3 -179.6(4) . . . . ?
N1 C7 C8 C9 179.8(3) . . . . ?
N1 C6 C5 Cl1 2.8(4) . . . . ?
N1 C6 C5 C4 -177.7(3) . . . . ?
N1 C6 C1 Cl2 -2.3(4) . . . . ?
N1 C6 C1 C2 177.0(4) . . . . ?
N4 N3 C14 O1 -1.9(5) . . . . ?
N4 N3 C14 N2 178.2(3) . . . . ?
C12 C11 C10 C9 -0.3(5) . . . . ?
C12 C7 C8 C9 0.6(5) . . . . ?
C14 N2 C13 C12 -170.2(3) . . . . ?
C11 C12 C7 N1 179.8(3) . . . . ?
C11 C12 C7 C8 -1.0(4) . . . . ?
C11 C12 C13 N2 -112.8(3) . . . . ?
C11 C10 C9 C8 0.0(5) . . . . ?
C7 N1 C6 C5 -88.3(4) . . . . ?
C7 N1 C6 C1 92.8(4) . . . . ?
C7 C12 C11 C10 0.8(4) . . . . ?
C7 C12 C13 N2 69.5(4) . . . . ?
C7 C8 C9 C10 -0.1(5) . . . . ?
C6 N1 C7 C12 -166.1(3) . . . . ?
C6 N1 C7 C8 14.7(4) . . . . ?
C6 C5 C4 C3 0.2(6) . . . . ?
C6 C1 C2 C3 1.1(7) . . . . ?
C13 N2 C14 O1 4.1(5) . . . . ?
C13 N2 C14 N3 -176.0(3) . . . . ?
C13 C12 C11 C10 -176.9(3) . . . . ?
C13 C12 C7 N1 -2.5(4) . . . . ?
C13 C12 C7 C8 176.7(3) . . . . ?
C5 C6 C1 Cl2 178.7(3) . . . . ?
C5 C6 C1 C2 -2.0(5) . . . . ?
C5 C4 C3 C2 -1.2(7) . . . . ?
C4 C3 C2 C1 0.5(7) . . . . ?
C1 C6 C5 Cl1 -178.2(3) . . . . ?
C1 C6 C5 C4 1.3(5) . . . . ?

_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_Nap_az
_database_code_depnum_ccdc_archive 'CCDC 2049307'
loop_
_audit_author_name
_audit_author_address
'Sabir Ahmed'
;Research fellow
India
;
_audit_update_record             
;
2020-12-09 deposited with the CCDC.	2026-03-27 downloaded from the CCDC.
;
_audit_creation_date             2020-12-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H14 N4 O2'
_chemical_formula_sum            'C14 H14 N4 O2'
_chemical_formula_weight         270.29
_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                   13.9443(10)
_cell_length_b                   5.2071(4)
_cell_length_c                   18.4952(12)
_cell_angle_alpha                90
_cell_angle_beta                 94.240(2)
_cell_angle_gamma                90
_cell_volume                     1339.25(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3883
_cell_measurement_temperature    120.1
_cell_measurement_theta_max      28.97
_cell_measurement_theta_min      2.56
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.4538
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1527 before and 0.0985 after correction. The Ratio of minimum to maximum transmission is 0.6084. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.2
_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  0.0822
_diffrn_reflns_av_unetI/netI     0.0700
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13240
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.098
_diffrn_reflns_theta_min         2.558
_diffrn_ambient_temperature      120.1
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2318
_reflns_number_total             2946
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2946
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0487
_refine_ls_restrained_S_all      1.051
_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)+(0.0468P)²+0.3732P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1227
_refine_ls_wR_factor_ref         0.1323
_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
2.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C6(H6), C7(H7), C10(H10), C2(H2), C3(H3), C8(H8)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.11423(9) -0.0605(2) 0.55273(6) 0.0299(3) Uani 1 1 d . . . . .
O2 O 0.55430(9) 0.3188(3) 0.94052(7) 0.0391(4) Uani 1 1 d . . . . .
N1 N 0.11075(10) 0.3661(3) 0.57876(7) 0.0236(3) Uani 1 1 d . . . . .
H1 H 0.111216 0.521436 0.560054 0.028 Uiso 1 1 calc R . . . .
N3 N 0.13098(11) 0.0634(3) 0.41983(7) 0.0277(3) Uani 1 1 d . . . . .
N2 N 0.12925(10) 0.2489(3) 0.46277(7) 0.0267(3) Uani 1 1 d . . . . .
C1 C 0.19923(12) 0.3540(3) 0.69982(8) 0.0209(3) Uani 1 1 d . . . . .
N4 N 0.13321(13) -0.0864(3) 0.37667(8) 0.0403(4) Uani 1 1 d . . . . .
C13 C 0.11727(11) 0.1651(3) 0.53542(8) 0.0214(3) Uani 1 1 d . . . . .
C11 C 0.10278(11) 0.3373(3) 0.65698(7) 0.0213(3) Uani 1 1 d . . . . .
H11 H 0.074429 0.164730 0.665825 0.026 Uiso 1 1 calc R . . . .
C6 C 0.22225(12) 0.1892(3) 0.75593(8) 0.0221(3) Uani 1 1 d . . . . .
H6 H 0.180244 0.050443 0.764288 0.027 Uiso 1 1 calc R . . . .
C4 C 0.37058(11) 0.4250(3) 0.78854(8) 0.0237(4) Uani 1 1 d . . . . .
C5 C 0.30729(12) 0.2204(3) 0.80196(8) 0.0229(4) Uani 1 1 d . . . . .
C12 C 0.03432(12) 0.5417(3) 0.68215(8) 0.0263(4) Uani 1 1 d . . . . .
H12A H 0.059600 0.712559 0.672074 0.039 Uiso 1 1 calc GR . . . .
H12B H 0.028390 0.523410 0.734369 0.039 Uiso 1 1 calc GR . . . .
H12C H -0.029030 0.520415 0.656186 0.039 Uiso 1 1 calc GR . . . .
C7 C 0.33155(13) 0.0562(3) 0.86177(9) 0.0296(4) Uani 1 1 d . . . . .
H7 H 0.290346 -0.083069 0.871308 0.035 Uiso 1 1 calc R . . . .
C10 C 0.45487(12) 0.4640(3) 0.83521(9) 0.0283(4) Uani 1 1 d . . . . .
H10 H 0.497115 0.602046 0.826619 0.034 Uiso 1 1 calc R . . . .
C9 C 0.47493(12) 0.3024(4) 0.89246(9) 0.0291(4) Uani 1 1 d . . . . .
C2 C 0.26352(13) 0.5560(3) 0.68638(9) 0.0284(4) Uani 1 1 d . . . . .
H2 H 0.248642 0.669887 0.647022 0.034 Uiso 1 1 calc R . . . .
C3 C 0.34625(13) 0.5891(4) 0.72904(9) 0.0297(4) Uani 1 1 d . . . . .
H3 H 0.388533 0.725171 0.718698 0.036 Uiso 1 1 calc R . . . .
C8 C 0.41284(13) 0.0952(4) 0.90561(9) 0.0313(4) Uani 1 1 d . . . . .
H8 H 0.428054 -0.017142 0.945275 0.038 Uiso 1 1 calc R . . . .
C14 C 0.61633(14) 0.5341(4) 0.93297(11) 0.0428(5) Uani 1 1 d . . . . .
H14A H 0.641602 0.530188 0.884926 0.064 Uiso 1 1 calc GR . . . .
H14B H 0.669814 0.526323 0.970378 0.064 Uiso 1 1 calc GR . . . .
H14C H 0.580097 0.693292 0.938416 0.064 Uiso 1 1 calc GR . . . .


_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 C13 1.2188(19) . ?
O2 C9 1.370(2) . ?
O2 C14 1.429(3) . ?
N1 H1 0.8800 . ?
N1 C13 1.326(2) . ?
N1 C11 1.4666(18) . ?
N3 N2 1.2517(19) . ?
N3 N4 1.118(2) . ?
N2 C13 1.4343(19) . ?
C1 C11 1.512(2) . ?
C1 C6 1.366(2) . ?
C1 C2 1.416(2) . ?
C11 H11 1.0000 . ?
C11 C12 1.525(2) . ?
C6 H6 0.9500 . ?
C6 C5 1.417(2) . ?
C4 C5 1.417(2) . ?
C4 C10 1.421(2) . ?
C4 C3 1.415(2) . ?
C5 C7 1.419(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C7 H7 0.9500 . ?
C7 C8 1.359(2) . ?
C10 H10 0.9500 . ?
C10 C9 1.365(2) . ?
C9 C8 1.416(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.360(2) . ?
C3 H3 0.9500 . ?
C8 H8 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O2 C14 116.82(15) . . ?
C13 N1 H1 119.0 . . ?
C13 N1 C11 121.95(13) . . ?
C11 N1 H1 119.0 . . ?
N4 N3 N2 173.74(17) . . ?
N3 N2 C13 111.64(13) . . ?
C6 C1 C11 120.78(15) . . ?
C6 C1 C2 118.92(15) . . ?
C2 C1 C11 120.06(14) . . ?
O1 C13 N1 126.64(14) . . ?
O1 C13 N2 123.22(14) . . ?
N1 C13 N2 110.14(13) . . ?
N1 C11 C1 112.44(13) . . ?
N1 C11 H11 108.2 . . ?
N1 C11 C12 108.93(12) . . ?
C1 C11 H11 108.2 . . ?
C1 C11 C12 110.63(13) . . ?
C12 C11 H11 108.2 . . ?
C1 C6 H6 119.2 . . ?
C1 C6 C5 121.56(15) . . ?
C5 C6 H6 119.2 . . ?
C5 C4 C10 119.96(15) . . ?
C3 C4 C5 118.29(15) . . ?
C3 C4 C10 121.74(16) . . ?
C6 C5 C7 122.67(15) . . ?
C4 C5 C6 119.04(14) . . ?
C4 C5 C7 118.28(15) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C5 C7 H7 119.5 . . ?
C8 C7 C5 121.02(17) . . ?
C8 C7 H7 119.5 . . ?
C4 C10 H10 120.1 . . ?
C9 C10 C4 119.72(17) . . ?
C9 C10 H10 120.1 . . ?
O2 C9 C8 114.27(15) . . ?
C10 C9 O2 125.04(17) . . ?
C10 C9 C8 120.68(16) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 C1 120.91(15) . . ?
C3 C2 H2 119.5 . . ?
C4 C3 H3 119.4 . . ?
C2 C3 C4 121.26(16) . . ?
C2 C3 H3 119.4 . . ?
C7 C8 C9 120.33(16) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_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_Flur_az
_database_code_depnum_ccdc_archive 'CCDC 2049308'
loop_
_audit_author_name
_audit_author_address
'Sabir Ahmed'
;Research fellow
India
;
_audit_update_record             
;
2020-12-09 deposited with the CCDC.	2026-03-27 downloaded from the CCDC.
;
_audit_creation_date             2020-12-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H13 F N4 O, C15 H10 F N4 O'
_chemical_formula_sum            'C30 H23 F2 N8 O2'
_chemical_formula_weight         565.56
_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                   6.516(2)
_cell_length_b                   10.111(3)
_cell_length_c                   21.318(7)
_cell_angle_alpha                91.568(5)
_cell_angle_beta                 92.708(5)
_cell_angle_gamma                103.339(5)
_cell_volume                     1363.9(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1533
_cell_measurement_temperature    124.38
_cell_measurement_theta_max      19.135
_cell_measurement_theta_min      2.872
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_correction_T_min  0.6506
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1200 before and 0.0682 after correction. The Ratio of minimum to maximum transmission is 0.8734. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             586
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1276
_diffrn_reflns_av_unetI/netI     0.0985
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            20695
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        22.986
_diffrn_reflns_theta_max         22.986
_diffrn_reflns_theta_min         0.957
_diffrn_ambient_temperature      124.38
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2160
_reflns_number_total             3779
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.620
_refine_diff_density_min         -0.451
_refine_diff_density_rms         0.123
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     385
_refine_ls_number_reflns         3779
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1869
_refine_ls_R_factor_gt           0.1198
_refine_ls_restrained_S_all      1.141
_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)+(0.1328P)²+13.3675P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3398
_refine_ls_wR_factor_ref         0.3780
_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
2. Others
 Sof(H23A)=Sof(F2B)=Sof(C18B)=Sof(C19B)=Sof(C20B)=Sof(C21A)=Sof(C22A)=
 Sof(C17A)=1-FVAR(1)
 Sof(H23)=Sof(F2A)=Sof(C22B)=Sof(C17B)=Sof(C21B)=Sof(C18A)=Sof(C19A)=Sof(C20A)=
 FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C13(H13), C23(H23A), C23(H23)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N5(H5), C6(H6), C2(H2), C3(H3), C12(H12), C8(H8), C11(H11), C20(H20),
 C17(H17), C21(H21), C10(H10), C18(H18), C19(H19), C9(H9)
3.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.4163(9) 0.5455(6) 0.7503(3) 0.0365(16) Uani 1 1 d . . . . .
O1 O 0.8744(10) 1.0023(6) 0.5734(3) 0.0246(16) Uani 1 1 d . . . . .
O2 O 0.8726(10) 0.5027(7) 0.5766(3) 0.0272(17) Uani 1 1 d . . . . .
N1 N 0.9150(12) 0.7921(8) 0.5974(4) 0.0238(19) Uani 1 1 d . . . . .
H1 H 0.888440 0.706242 0.584308 0.029 Uiso 1 1 calc R . . . .
N2 N 0.7408(11) 0.8161(8) 0.5054(4) 0.0237(19) Uani 1 1 d . . . . .
N6 N 0.7514(12) 0.3187(8) 0.5059(4) 0.0260(19) Uani 1 1 d . . . . .
N3 N 0.6769(13) 0.8979(9) 0.4703(4) 0.028(2) Uani 1 1 d . . . . .
N5 N 0.9300(12) 0.2952(8) 0.5956(4) 0.0251(19) Uani 1 1 d . . . . .
H5 H 0.917534 0.212292 0.579737 0.030 Uiso 1 1 calc R . . . .
N7 N 0.6836(12) 0.4005(9) 0.4711(4) 0.029(2) Uani 1 1 d . . . . .
N8 N 0.6185(14) 0.4631(10) 0.4369(4) 0.037(2) Uani 1 1 d . . . . .
C15 C 0.8510(13) 0.8820(10) 0.5606(4) 0.020(2) Uani 1 1 d . . . . .
C6 C 0.7063(16) 0.6836(9) 0.7074(5) 0.026(2) Uani 1 1 d . . . . .
H6 H 0.675305 0.628369 0.669858 0.032 Uiso 1 1 calc R . . . .
C25 C 0.8559(13) 0.3816(9) 0.5624(4) 0.018(2) Uani 1 1 d . . . . .
C5 C 0.5820(13) 0.6546(10) 0.7577(5) 0.023(2) Uani 1 1 d . . . . .
N4 N 0.6138(15) 0.9608(10) 0.4357(5) 0.041(2) Uani 1 1 d . . . . .
C13 C 1.0275(13) 0.8318(9) 0.6586(4) 0.021(2) Uani 1 1 d . . . . .
H13 H 1.082484 0.932760 0.660240 0.025 Uiso 1 1 calc R . . . .
C4 C 0.6145(16) 0.7304(10) 0.8139(5) 0.028(2) Uani 1 1 d . . . . .
C16 C 0.4129(17) 0.1820(11) 0.8484(5) 0.034(3) Uani 1 1 d . . . . .
C1 C 0.8793(15) 0.7955(10) 0.7121(5) 0.025(2) Uani 1 1 d . . . . .
C7 C 0.4753(16) 0.6968(11) 0.8678(5) 0.032(3) Uani 1 1 d . . . . .
C23 C 1.0338(15) 0.3305(9) 0.6588(5) 0.026(2) Uani 1 1 d . . . . .
H23A H 1.088529 0.431454 0.662690 0.031 Uiso 0.458(14) 1 calc R . P A 2
H23 H 1.091205 0.431286 0.661620 0.031 Uiso 0.542(14) 1 calc R . P A 1
C2 C 0.9194(16) 0.8700(10) 0.7685(5) 0.033(3) Uani 1 1 d . . . . .
H2 H 1.038781 0.944697 0.773194 0.039 Uiso 1 1 calc R . . . .
C3 C 0.7911(17) 0.8388(11) 0.8178(5) 0.038(3) Uani 1 1 d . . . . .
H3 H 0.823846 0.892863 0.855671 0.045 Uiso 1 1 calc R . . . .
C24 C 1.2179(14) 0.2643(10) 0.6682(5) 0.027(2) Uani 1 1 d . . . . .
H24A H 1.169474 0.165886 0.659955 0.041 Uiso 1 1 calc GR . . . .
H24B H 1.276697 0.282187 0.711618 0.041 Uiso 1 1 calc GR . . . .
H24C H 1.327023 0.301765 0.639255 0.041 Uiso 1 1 calc GR . . . .
C14 C 1.2143(15) 0.7671(10) 0.6656(5) 0.030(2) Uani 1 1 d . . . . .
H14A H 1.167035 0.668751 0.657047 0.045 Uiso 1 1 calc GR . . . .
H14B H 1.277305 0.784552 0.708586 0.045 Uiso 1 1 calc GR . . . .
H14C H 1.319671 0.806067 0.635822 0.045 Uiso 1 1 calc GR . . . .
C12 C 0.2591(16) 0.6594(11) 0.8592(5) 0.037(3) Uani 1 1 d . . . . .
H12 H 0.195595 0.653150 0.817829 0.044 Uiso 1 1 calc R . . . .
C8 C 0.5680(17) 0.7035(12) 0.9289(5) 0.042(3) Uani 1 1 d . . . . .
H8 H 0.717205 0.730375 0.935569 0.050 Uiso 1 1 calc R . . . .
C11 C 0.1318(17) 0.6305(11) 0.9096(6) 0.042(3) Uani 1 1 d . . . . .
H11 H -0.017600 0.605789 0.902877 0.050 Uiso 1 1 calc R . . . .
C20 C 0.236(2) 0.0296(12) 0.9236(6) 0.051(3) Uani 1 1 d . . . . .
H20 H 0.224606 -0.049991 0.947077 0.061 Uiso 1 1 calc R . . . .
C17 C 0.2712(17) 0.2639(12) 0.8570(5) 0.040(3) Uani 1 1 d . . . . .
H17 H 0.283416 0.344688 0.834328 0.048 Uiso 1 1 calc R . . . .
C21 C 0.3909(18) 0.0643(11) 0.8815(6) 0.044(3) Uani 1 1 d . . . . .
H21 H 0.484522 0.006389 0.875039 0.052 Uiso 1 1 calc R . . . .
C10 C 0.2236(18) 0.6381(13) 0.9695(6) 0.050(3) Uani 1 1 d . . . . .
H10 H 0.135621 0.620628 1.004044 0.060 Uiso 1 1 calc R . . . .
C18 C 0.1110(18) 0.2276(14) 0.8988(5) 0.045(3) Uani 1 1 d . . . . .
H18 H 0.013329 0.283132 0.904305 0.054 Uiso 1 1 calc R . . . .
F2B F 0.6937(19) 0.4338(11) 0.8464(6) 0.033(4) Uani 0.458(14) 1 d . . P A 2
C19 C 0.0952(18) 0.1131(13) 0.9313(6) 0.046(3) Uani 1 1 d . . . . .
H19 H -0.013568 0.089133 0.959922 0.055 Uiso 1 1 calc R . . . .
C9 C 0.4398(19) 0.6703(14) 0.9807(6) 0.052(3) Uani 1 1 d . . . . .
H9 H 0.501171 0.670233 1.021999 0.063 Uiso 1 1 calc R . . . .
F2A F 0.4709(17) 0.0096(11) 0.7508(5) 0.040(4) Uani 0.542(14) 1 d . . P A 1
C22B C 0.698(5) 0.336(4) 0.8048(13) 0.022(11) Uiso 0.542(14) 1 d . . P A 2
C17B C 0.588(6) 0.225(4) 0.8067(17) 0.025(14) Uiso 0.542(14) 1 d . . P A 2
C18B C 0.598(9) 0.118(6) 0.759(2) 0.03(2) Uiso 0.458(14) 1 d . . P A 2
C19B C 0.755(5) 0.166(4) 0.7137(17) 0.015(11) Uiso 0.458(14) 1 d . . P A 2
C20B C 0.862(7) 0.285(5) 0.713(2) 0.029(19) Uiso 0.458(14) 1 d . . P A 2
C21B C 0.851(9) 0.384(6) 0.758(3) 0.02(2) Uiso 0.542(14) 1 d . . P A 2
C18A C 0.604(6) 0.134(4) 0.7520(18) 0.018(13) Uiso 0.542(14) 1 d . . P A 1
C19A C 0.736(5) 0.154(4) 0.7030(16) 0.030(12) Uiso 0.542(14) 1 d . . P A 1
C20A C 0.885(5) 0.297(4) 0.7070(16) 0.011(12) Uiso 0.542(14) 1 d . . P A 1
C21A C 0.867(11) 0.386(8) 0.754(3) 0.03(3) Uiso 0.458(14) 1 d . . P A 1
C22A C 0.723(5) 0.360(3) 0.7967(17) 0.019(12) Uiso 0.458(14) 1 d . . P A 1
C17A C 0.572(7) 0.213(4) 0.797(2) 0.022(15) Uiso 0.458(14) 1 d . . P A 1


_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 C5 1.353(10) . ?
O1 C15 1.212(10) . ?
O2 C25 1.232(11) . ?
N1 H1 0.8800 . ?
N1 C15 1.341(12) . ?
N1 C13 1.465(11) . ?
N2 N3 1.257(12) . ?
N2 C15 1.416(12) . ?
N6 N7 1.266(12) . ?
N6 C25 1.414(12) . ?
N3 N4 1.111(12) . ?
N5 H5 0.8800 . ?
N5 C25 1.301(12) . ?
N5 C23 1.474(12) . ?
N7 N8 1.109(11) . ?
C6 H6 0.9500 . ?
C6 C5 1.372(14) . ?
C6 C1 1.398(14) . ?
C5 C4 1.385(14) . ?
C13 H13 1.0000 . ?
C13 C1 1.528(14) . ?
C13 C14 1.513(12) . ?
C4 C7 1.494(14) . ?
C4 C3 1.391(14) . ?
C16 C17 1.389(15) . ?
C16 C21 1.382(16) . ?
C16 C17B 1.47(4) . ?
C16 C17A 1.53(5) . ?
C1 C2 1.381(14) . ?
C7 C12 1.374(14) . ?
C7 C8 1.403(15) . ?
C23 H23A 1.0000 . ?
C23 H23 1.0000 . ?
C23 C24 1.512(13) . ?
C23 C20B 1.64(5) . ?
C23 C20A 1.44(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.372(15) . ?
C3 H3 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C12 H12 0.9500 . ?
C12 C11 1.384(15) . ?
C8 H8 0.9500 . ?
C8 C9 1.417(16) . ?
C11 H11 0.9500 . ?
C11 C10 1.378(17) . ?
C20 H20 0.9500 . ?
C20 C21 1.374(16) . ?
C20 C19 1.393(17) . ?
C17 H17 0.9500 . ?
C17 C18 1.395(16) . ?
C21 H21 0.9500 . ?
C10 H10 0.9500 . ?
C10 C9 1.378(16) . ?
C18 H18 0.9500 . ?
C18 C19 1.352(17) . ?
F2B C22B 1.31(3) . ?
C19 H19 0.9500 . ?
C9 H9 0.9500 . ?
F2A C18A 1.35(4) . ?
C22B C17B 1.19(4) . ?
C22B C21B 1.45(7) . ?
C17B C18B 1.49(7) . ?
C18B C19B 1.44(6) . ?
C19B C20B 1.25(5) . ?
C20B C21B 1.39(8) . ?
C18A C19A 1.37(5) . ?
C18A C17A 1.30(6) . ?
C19A C20A 1.53(5) . ?
C20A C21A 1.35(8) . ?
C21A C22A 1.33(9) . ?
C22A C17A 1.58(6) . ?

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
C15 N1 H1 118.8 . . ?
C15 N1 C13 122.3(8) . . ?
C13 N1 H1 118.8 . . ?
N3 N2 C15 112.0(8) . . ?
N7 N6 C25 113.0(8) . . ?
N4 N3 N2 173.9(10) . . ?
C25 N5 H5 118.7 . . ?
C25 N5 C23 122.7(8) . . ?
C23 N5 H5 118.7 . . ?
N8 N7 N6 174.0(10) . . ?
O1 C15 N1 125.5(9) . . ?
O1 C15 N2 123.8(8) . . ?
N1 C15 N2 110.6(8) . . ?
C5 C6 H6 120.4 . . ?
C5 C6 C1 119.2(9) . . ?
C1 C6 H6 120.4 . . ?
O2 C25 N6 122.9(8) . . ?
O2 C25 N5 126.2(9) . . ?
N5 C25 N6 111.0(8) . . ?
F1 C5 C6 116.5(9) . . ?
F1 C5 C4 119.3(9) . . ?
C6 C5 C4 124.2(9) . . ?
N1 C13 H13 108.0 . . ?
N1 C13 C1 111.1(7) . . ?
N1 C13 C14 110.2(7) . . ?
C1 C13 H13 108.0 . . ?
C14 C13 H13 108.0 . . ?
C14 C13 C1 111.4(8) . . ?
C5 C4 C7 122.9(9) . . ?
C5 C4 C3 115.2(9) . . ?
C3 C4 C7 121.8(9) . . ?
C17 C16 C17B 119.5(17) . . ?
C17 C16 C17A 119.9(19) . . ?
C21 C16 C17 118.9(10) . . ?
C21 C16 C17B 121.5(17) . . ?
C21 C16 C17A 120.8(19) . . ?
C6 C1 C13 122.0(8) . . ?
C2 C1 C6 117.7(9) . . ?
C2 C1 C13 120.2(9) . . ?
C12 C7 C4 121.9(10) . . ?
C12 C7 C8 119.0(10) . . ?
C8 C7 C4 119.1(9) . . ?
N5 C23 H23A 108.4 . . ?
N5 C23 H23 107.6 . . ?
N5 C23 C24 110.8(8) . . ?
N5 C23 C20B 110.0(19) . . ?
C24 C23 H23A 108.4 . . ?
C24 C23 H23 107.6 . . ?
C24 C23 C20B 110.7(18) . . ?
C20B C23 H23A 108.4 . . ?
C20A C23 N5 111.3(15) . . ?
C20A C23 H23 107.6 . . ?
C20A C23 C24 111.8(15) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 C1 121.6(10) . . ?
C3 C2 H2 119.2 . . ?
C4 C3 H3 119.0 . . ?
C2 C3 C4 122.0(10) . . ?
C2 C3 H3 119.0 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C7 C12 H12 119.3 . . ?
C7 C12 C11 121.3(11) . . ?
C11 C12 H12 119.3 . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.2(10) . . ?
C9 C8 H8 119.9 . . ?
C12 C11 H11 120.3 . . ?
C10 C11 C12 119.4(11) . . ?
C10 C11 H11 120.3 . . ?
C21 C20 H20 120.5 . . ?
C21 C20 C19 119.0(12) . . ?
C19 C20 H20 120.5 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.1(11) . . ?
C18 C17 H17 119.9 . . ?
C16 C21 H21 119.4 . . ?
C20 C21 C16 121.1(11) . . ?
C20 C21 H21 119.4 . . ?
C11 C10 H10 119.1 . . ?
C11 C10 C9 121.8(11) . . ?
C9 C10 H10 119.1 . . ?
C17 C18 H18 120.1 . . ?
C19 C18 C17 119.8(11) . . ?
C19 C18 H18 120.1 . . ?
C20 C19 H19 119.5 . . ?
C18 C19 C20 121.1(11) . . ?
C18 C19 H19 119.5 . . ?
C8 C9 H9 120.9 . . ?
C10 C9 C8 118.2(12) . . ?
C10 C9 H9 120.9 . . ?
F2B C22B C21B 111(3) . . ?
C17B C22B F2B 122(3) . . ?
C17B C22B C21B 126(4) . . ?
C16 C17B C18B 113(3) . . ?
C22B C17B C16 126(3) . . ?
C22B C17B C18B 121(4) . . ?
C19B C18B C17B 112(4) . . ?
C20B C19B C18B 125(4) . . ?
C19B C20B C23 121(4) . . ?
C19B C20B C21B 122(5) . . ?
C21B C20B C23 117(5) . . ?
C20B C21B C22B 114(5) . . ?
F2A C18A C19A 114(3) . . ?
C17A C18A F2A 113(3) . . ?
C17A C18A C19A 133(4) . . ?
C18A C19A C20A 112(3) . . ?
C23 C20A C19A 118(3) . . ?
C21A C20A C23 123(4) . . ?
C21A C20A C19A 119(4) . . ?
C22A C21A C20A 124(6) . . ?
C21A C22A C17A 119(4) . . ?
C16 C17A C22A 119(3) . . ?
C18A C17A C16 129(4) . . ?
C18A C17A C22A 112(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
#
_vrf_THETM01_Flur_az             
;
PROBLEM:  The value of sine(theta_max)/wavelength is less than 0.550
            Calculated sin(theta_max)/wavelength =    0.5494
RESPONSE: The crystal was poorly diffracting and did not diffracted at
higher bragg angles. The data quality was very poor and did not
improved with multiple data collection.
;
_vrf_PLAT084_Flur_az             
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.38 Report
RESPONSE: The crystal was poorly diffracting and the data quality was very 
poor. It was not further improved with multiple data collection.
The quality of crystals are also very poor.
Also, The crytal have Z' problem having more than one molecule in the
asymmetric unit. Thus more number of parameters has to be refined in 
the asymmetric unit for the refinement to converge. Thus it showed 
higher wR2 value.
;
_vrf_PLAT201_Flur_az             
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......          6 Report
          C17B      C18A      C19A      C20A      C21B                etc.
RESPONSE: Certain disorder atoms were kept isotropic as anisotropic
refinement did not further improve the data quality.
;
_vrf_PLAT340_Flur_az             
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01564 Ang.  
RESPONSE: This alert is due to the poor data quality.
;
# end Validation reply form
####################################################################### 
# 
# 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_mo_pd201223_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2432622'
loop_
_audit_author_name
_audit_author_address
'Manoj Kumar Baskey'
;Indian Association for the Cultivation of Science
India
;
_audit_update_record             
;
2025-03-20 deposited with the CCDC.	2026-03-27 downloaded from the CCDC.
;
_audit_creation_date             2025-03-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H14 N4 O2'
_chemical_formula_sum            'C16 H14 N4 O2'
_chemical_formula_weight         294.31
_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                   19.98(2)
_cell_length_b                   4.808(5)
_cell_length_c                   14.863(12)
_cell_angle_alpha                90
_cell_angle_beta                 91.84(4)
_cell_angle_gamma                90
_cell_volume                     1427(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1534
_cell_measurement_temperature    160(2)
_cell_measurement_theta_max      25.19
_cell_measurement_theta_min      2.89
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5183
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
TWINABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1552 before and 0.0959 after correction.
The Ratio of minimum to maximum transmission is 0.6955.
The λ/2 correction factor is Not present.
;
_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    1.370
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_preparation       SYNTHESIS
_exptl_crystal_recrystallization_method 'SLOW EVAPORATION'
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.075
_diffrn_reflns_av_unetI/netI     0.1779
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2507
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.046
_diffrn_reflns_theta_max         25.046
_diffrn_reflns_theta_min         2.742
_diffrn_ambient_temperature      159.97
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1367
_reflns_number_total             2507
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.493
_refine_diff_density_rms         0.113
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2507
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1880
_refine_ls_R_factor_gt           0.1227
_refine_ls_restrained_S_all      1.026
_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)+(0.1958P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3035
_refine_ls_wR_factor_ref         0.3466
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.89008
 0.10992
2.a Ternary CH refined with riding coordinates:
 C14(H14)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C10(H10), C11(H11), C9(H9), C1(H1A), C13(H13), C2(H2), C5(H5), C4(H4),
  C3(H3)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O2 O 0.4086(2) 1.0794(10) 0.4714(3) 0.0374(13) Uani 1 1 d . . . . .
O1 O 0.1277(2) 0.0517(12) 0.6253(3) 0.0443(14) Uani 1 1 d . . . . .
N2 N 0.4574(3) 0.6938(13) 0.4081(4) 0.0360(15) Uani 1 1 d . . . . .
N3 N 0.4909(3) 0.8690(12) 0.3652(3) 0.0331(14) Uani 1 1 d . . . . .
N1 N 0.3752(3) 0.6488(12) 0.5091(3) 0.0301(14) Uani 1 1 d . . . . .
H1 H 0.385252 0.470683 0.507988 0.036 Uiso 1 1 calc R U . . .
C12 C 0.3003(3) 0.5308(14) 0.6316(4) 0.0280(16) Uani 1 1 d . . . . .
C7 C 0.1572(3) 0.0819(15) 0.6984(4) 0.0317(16) Uani 1 1 d . . . . .
C16 C 0.4121(3) 0.8290(14) 0.4654(4) 0.0285(15) Uani 1 1 d . . . . .
C10 C 0.3365(3) 0.2609(15) 0.7613(4) 0.0300(16) Uani 1 1 d . . . . .
H10 H 0.370619 0.207039 0.803746 0.036 Uiso 1 1 calc R U . . .
C11 C 0.3500(4) 0.4548(15) 0.6960(4) 0.0340(17) Uani 1 1 d . . . . .
H11 H 0.393138 0.537298 0.694452 0.041 Uiso 1 1 calc R U . . .
C14 C 0.3166(3) 0.7459(14) 0.5601(4) 0.0289(15) Uani 1 1 d . . . . .
H14 H 0.330211 0.920822 0.592196 0.035 Uiso 1 1 calc R U . . .
N4 N 0.5216(3) 1.0046(15) 0.3227(4) 0.0503(19) Uani 1 1 d . . . . .
C9 C 0.2737(3) 0.1456(15) 0.7651(4) 0.0321(17) Uani 1 1 d . . . . .
H9 H 0.264340 0.017373 0.811697 0.039 Uiso 1 1 calc R U . . .
C8 C 0.2238(3) 0.2138(14) 0.7019(4) 0.0269(15) Uani 1 1 d . . . . .
C6 C 0.1253(3) -0.0161(15) 0.7817(4) 0.0304(16) Uani 1 1 d . . . . .
C15 C 0.2604(4) 0.8176(16) 0.4957(4) 0.0376(18) Uani 1 1 d . . . . .
H15A H 0.244904 0.648976 0.464431 0.056 Uiso 1 1 calc R U . . .
H15B H 0.276009 0.952644 0.451664 0.056 Uiso 1 1 calc R U . . .
H15C H 0.223453 0.898325 0.528754 0.056 Uiso 1 1 calc R U . . .
C1 C 0.1353(3) 0.1155(17) 0.8640(4) 0.0371(18) Uani 1 1 d . . . . .
H1A H 0.166776 0.263052 0.869812 0.044 Uiso 1 1 calc R U . . .
C13 C 0.2385(3) 0.4140(14) 0.6357(4) 0.0311(16) Uani 1 1 d . . . . .
H13 H 0.204462 0.468030 0.593121 0.037 Uiso 1 1 calc R U . . .
C2 C 0.0998(4) 0.0332(19) 0.9379(4) 0.044(2) Uani 1 1 d . . . . .
H2 H 0.105841 0.128564 0.993525 0.052 Uiso 1 1 calc R U . . .
C5 C 0.0787(3) -0.2338(17) 0.7749(5) 0.0393(18) Uani 1 1 d . . . . .
H5 H 0.070327 -0.324831 0.718934 0.047 Uiso 1 1 calc R U . . .
C4 C 0.0451(4) -0.3142(18) 0.8500(5) 0.045(2) Uani 1 1 d . . . . .
H4 H 0.013765 -0.462614 0.845816 0.054 Uiso 1 1 calc R U . . .
C3 C 0.0566(4) -0.181(2) 0.9312(5) 0.052(2) Uani 1 1 d . . . . .
H3 H 0.033831 -0.241680 0.982810 0.062 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
O2 C16 1.210(8) . ?
O1 C7 1.228(7) . ?
N2 N3 1.261(8) . ?
N2 C16 1.420(8) . ?
N3 N4 1.107(8) . ?
N1 H1 0.8800 . ?
N1 C16 1.322(9) . ?
N1 C14 1.491(8) . ?
C12 C11 1.404(9) . ?
C12 C14 1.525(9) . ?
C12 C13 1.360(9) . ?
C7 C8 1.475(9) . ?
C7 C6 1.486(9) . ?
C10 H10 0.9500 . ?
C10 C11 1.379(9) . ?
C10 C9 1.374(10) . ?
C11 H11 0.9500 . ?
C14 H14 1.0000 . ?
C14 C15 1.492(9) . ?
C9 H9 0.9500 . ?
C9 C8 1.387(9) . ?
C8 C13 1.414(9) . ?
C6 C1 1.386(9) . ?
C6 C5 1.403(10) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C1 H1A 0.9500 . ?
C1 C2 1.384(10) . ?
C13 H13 0.9500 . ?
C2 H2 0.9500 . ?
C2 C3 1.347(12) . ?
C5 H5 0.9500 . ?
C5 C4 1.376(10) . ?
C4 H4 0.9500 . ?
C4 C3 1.378(11) . ?
C3 H3 0.9500 . ?

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
N3 N2 C16 110.9(6) . . ?
N4 N3 N2 173.9(7) . . ?
C16 N1 H1 119.8 . . ?
C16 N1 C14 120.3(6) . . ?
C14 N1 H1 119.8 . . ?
C11 C12 C14 119.3(6) . . ?
C13 C12 C11 119.0(6) . . ?
C13 C12 C14 121.7(6) . . ?
O1 C7 C8 119.2(5) . . ?
O1 C7 C6 119.6(6) . . ?
C8 C7 C6 121.2(6) . . ?
O2 C16 N2 122.6(6) . . ?
O2 C16 N1 125.5(6) . . ?
N1 C16 N2 111.8(6) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C11 120.1(6) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 C12 120.4(6) . . ?
C10 C11 H11 119.8 . . ?
N1 C14 C12 109.3(5) . . ?
N1 C14 H14 107.4 . . ?
N1 C14 C15 109.4(5) . . ?
C12 C14 H14 107.4 . . ?
C15 C14 C12 115.6(6) . . ?
C15 C14 H14 107.4 . . ?
C10 C9 H9 119.6 . . ?
C10 C9 C8 120.9(6) . . ?
C8 C9 H9 119.6 . . ?
C9 C8 C7 123.4(6) . . ?
C9 C8 C13 118.2(6) . . ?
C13 C8 C7 118.4(6) . . ?
C1 C6 C7 122.5(6) . . ?
C1 C6 C5 118.7(6) . . ?
C5 C6 C7 118.5(6) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C6 C1 H1A 119.8 . . ?
C2 C1 C6 120.5(7) . . ?
C2 C1 H1A 119.8 . . ?
C12 C13 C8 121.4(6) . . ?
C12 C13 H13 119.3 . . ?
C8 C13 H13 119.3 . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.3(7) . . ?
C3 C2 H2 119.9 . . ?
C6 C5 H5 120.3 . . ?
C4 C5 C6 119.4(7) . . ?
C4 C5 H5 120.3 . . ?
C5 C4 H4 119.7 . . ?
C5 C4 C3 120.6(8) . . ?
C3 C4 H4 119.7 . . ?
C2 C3 C4 120.5(7) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?

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 C7 C8 C9 -147.8(7) . . . . ?
O1 C7 C8 C13 30.2(9) . . . . ?
O1 C7 C6 C1 -147.9(7) . . . . ?
O1 C7 C6 C5 26.0(10) . . . . ?
N3 N2 C16 O2 -1.1(9) . . . . ?
N3 N2 C16 N1 178.3(5) . . . . ?
C7 C8 C13 C12 -175.9(6) . . . . ?
C7 C6 C1 C2 173.9(7) . . . . ?
C7 C6 C5 C4 -175.4(7) . . . . ?
C16 N1 C14 C12 -157.8(6) . . . . ?
C16 N1 C14 C15 74.7(7) . . . . ?
C10 C9 C8 C7 175.4(6) . . . . ?
C10 C9 C8 C13 -2.6(10) . . . . ?
C11 C12 C14 N1 57.2(7) . . . . ?
C11 C12 C14 C15 -178.9(6) . . . . ?
C11 C12 C13 C8 -1.4(9) . . . . ?
C11 C10 C9 C8 2.3(10) . . . . ?
C14 N1 C16 O2 10.1(10) . . . . ?
C14 N1 C16 N2 -169.2(5) . . . . ?
C14 C12 C11 C10 179.9(6) . . . . ?
C14 C12 C13 C8 179.7(6) . . . . ?
C9 C10 C11 C12 -1.5(10) . . . . ?
C9 C8 C13 C12 2.2(9) . . . . ?
C8 C7 C6 C1 32.4(10) . . . . ?
C8 C7 C6 C5 -153.6(6) . . . . ?
C6 C7 C8 C9 31.8(10) . . . . ?
C6 C7 C8 C13 -150.2(6) . . . . ?
C6 C1 C2 C3 2.1(11) . . . . ?
C6 C5 C4 C3 0.6(12) . . . . ?
C1 C6 C5 C4 -1.2(10) . . . . ?
C1 C2 C3 C4 -2.7(12) . . . . ?
C13 C12 C11 C10 1.1(9) . . . . ?
C13 C12 C14 N1 -124.0(6) . . . . ?
C13 C12 C14 C15 -0.1(9) . . . . ?
C5 C6 C1 C2 -0.1(10) . . . . ?
C5 C4 C3 C2 1.4(12) . . . . ?

_olex2_exptl_crystal_mounting_method LOOP
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.89008
2 0.10992

