# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_4Ae
_database_code_depnum_ccdc_archive 'CCDC 2224164'
loop_
_audit_author_name
_audit_author_address
'Bhupendra Mali'
;National Chemical Laboratory, Pune
India
;
_audit_update_record             
;
2022-12-08 deposited with the CCDC.	2023-03-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H10 Cl N3 O2'
_chemical_formula_sum            'C14 H10 Cl N3 O2'
_chemical_formula_weight         287.70

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.9044(6)
_cell_length_b                   6.9108(5)
_cell_length_c                   13.8175(11)
_cell_angle_alpha                91.301(3)
_cell_angle_beta                 100.548(3)
_cell_angle_gamma                103.119(3)
_cell_volume                     629.82(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9916
_cell_measurement_theta_min      3.01
_cell_measurement_theta_max      34.91

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_F_000             296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.308
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.964
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.955
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_process_details   'SADABS (Bruker, 2006)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_source_type              'Incoatech I\mS HB'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            44763
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.006
_diffrn_reflns_theta_max         35.237
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.929
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.929
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             5247
_reflns_number_gt                4508
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0406P)²+0.2173P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5247
_refine_ls_number_parameters     186
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.0891
_refine_ls_wR_factor_gt          0.0836
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.25289(3) 0.66123(3) 0.01681(2) 0.01689(6) Uani 1 1 d . . . . .
O1 O 0.85412(10) 0.93334(9) 0.39264(5) 0.01769(13) Uani 1 1 d . . . . .
O2 O 1.18362(10) 0.65417(10) 0.39747(5) 0.02006(14) Uani 1 1 d . . . . .
N1 N 1.07793(11) 0.77269(11) 0.24627(5) 0.01332(13) Uani 1 1 d . . . . .
H10 H 1.192(3) 0.848(2) 0.2424(12) 0.033(4) Uiso 1 1 d . . . . .
N2 N 0.47471(12) 0.08464(12) 0.24631(7) 0.02133(16) Uani 1 1 d . . . . .
N3 N 1.08578(13) 0.27496(13) 0.18774(8) 0.02468(17) Uani 1 1 d . . . . .
C1 C 0.67431(14) 0.83404(14) 0.52251(7) 0.01856(16) Uani 1 1 d . . . . .
H1 H 0.714964 0.976027 0.543894 0.028 Uiso 1 1 calc R U . . .
H4 H 0.724263 0.756852 0.576130 0.028 Uiso 1 1 calc R U . . .
H3 H 0.526131 0.792186 0.505304 0.028 Uiso 1 1 calc R U . . .
C2 C 0.76246(12) 0.79891(12) 0.43401(6) 0.01399(14) Uani 1 1 d . . . . .
C3 C 0.73081(13) 0.58255(12) 0.39891(6) 0.01516(15) Uani 1 1 d . . . . .
H9 H 0.583400 0.522851 0.380882 0.018 Uiso 1 1 calc R U . . .
H5 H 0.787380 0.510622 0.454240 0.018 Uiso 1 1 calc R U . . .
C4 C 0.82781(12) 0.55114(11) 0.31061(6) 0.01212(13) Uani 1 1 d . . . . .
C5 C 0.73760(12) 0.62742(11) 0.21552(6) 0.01104(13) Uani 1 1 d . . . . .
C6 C 0.53825(12) 0.59447(12) 0.16586(6) 0.01200(13) Uani 1 1 d . . . . .
H6 H 0.431194 0.508948 0.189601 0.014 Uiso 1 1 calc R U . . .
C7 C 0.50150(12) 0.69221(12) 0.07956(6) 0.01257(13) Uani 1 1 d . . . . .
C8 C 0.65670(13) 0.81493(12) 0.04248(6) 0.01400(14) Uani 1 1 d . . . . .
H2 H 0.626636 0.875598 -0.017700 0.017 Uiso 1 1 calc R U . . .
C9 C 1.05311(12) 0.66757(12) 0.32647(6) 0.01371(14) Uani 1 1 d . . . . .
C10 C 0.89284(12) 0.75539(11) 0.18040(6) 0.01133(13) Uani 1 1 d . . . . .
C11 C 0.85656(13) 0.84879(12) 0.09380(6) 0.01365(14) Uani 1 1 d . . . . .
H7 H 0.964125 0.933289 0.069965 0.016 Uiso 1 1 calc R U . . .
C12 C 0.83355(12) 0.32579(12) 0.30088(6) 0.01439(14) Uani 1 1 d . . . . .
H8 H 0.890312 0.288887 0.367927 0.017 Uiso 1 1 calc R U . . .
C13 C 0.63117(13) 0.19187(12) 0.26877(7) 0.01593(15) Uani 1 1 d . . . . .
C14 C 0.97000(13) 0.29257(13) 0.23501(7) 0.01764(16) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C7 1.7389(8) . ?
O1 C2 1.2166(10) . ?
O2 C9 1.2253(10) . ?
N1 C9 1.3545(11) . ?
N1 C10 1.4056(10) . ?
N1 H10 0.850(17) . ?
N2 C13 1.1471(11) . ?
N3 C14 1.1455(13) . ?
C1 C2 1.5002(13) . ?
C1 H1 0.9800 . ?
C1 H4 0.9800 . ?
C1 H3 0.9800 . ?
C2 C3 1.5161(12) . ?
C3 C4 1.5289(12) . ?
C3 H9 0.9900 . ?
C3 H5 0.9900 . ?
C4 C5 1.5077(11) . ?
C4 C9 1.5537(11) . ?
C4 C12 1.5702(11) . ?
C5 C6 1.3864(11) . ?
C5 C10 1.3950(11) . ?
C6 C7 1.3951(11) . ?
C6 H6 0.9500 . ?
C7 C8 1.3922(12) . ?
C8 C11 1.3962(12) . ?
C8 H2 0.9500 . ?
C10 C11 1.3819(11) . ?
C11 H7 0.9500 . ?
C12 C14 1.4736(13) . ?
C12 C13 1.4742(12) . ?
C12 H8 1.0000 . ?

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 N1 C10 111.55(7) . . ?
C9 N1 H10 121.3(11) . . ?
C10 N1 H10 126.8(11) . . ?
C2 C1 H1 109.5 . . ?
C2 C1 H4 109.5 . . ?
H1 C1 H4 109.5 . . ?
C2 C1 H3 109.5 . . ?
H1 C1 H3 109.5 . . ?
H4 C1 H3 109.5 . . ?
O1 C2 C1 122.97(8) . . ?
O1 C2 C3 121.55(8) . . ?
C1 C2 C3 115.48(7) . . ?
C2 C3 C4 114.28(7) . . ?
C2 C3 H9 108.7 . . ?
C4 C3 H9 108.7 . . ?
C2 C3 H5 108.7 . . ?
C4 C3 H5 108.7 . . ?
H9 C3 H5 107.6 . . ?
C5 C4 C3 115.46(7) . . ?
C5 C4 C9 101.93(6) . . ?
C3 C4 C9 112.21(7) . . ?
C5 C4 C12 113.52(6) . . ?
C3 C4 C12 108.18(6) . . ?
C9 C4 C12 105.00(6) . . ?
C6 C5 C10 120.73(7) . . ?
C6 C5 C4 130.71(7) . . ?
C10 C5 C4 108.51(7) . . ?
C5 C6 C7 117.18(7) . . ?
C5 C6 H6 121.4 . . ?
C7 C6 H6 121.4 . . ?
C8 C7 C6 122.29(7) . . ?
C8 C7 Cl1 118.93(6) . . ?
C6 C7 Cl1 118.79(6) . . ?
C7 C8 C11 119.96(7) . . ?
C7 C8 H2 120.0 . . ?
C11 C8 H2 120.0 . . ?
O2 C9 N1 127.55(8) . . ?
O2 C9 C4 124.46(7) . . ?
N1 C9 C4 107.87(7) . . ?
C11 C10 C5 121.94(7) . . ?
C11 C10 N1 128.18(7) . . ?
C5 C10 N1 109.86(7) . . ?
C10 C11 C8 117.84(7) . . ?
C10 C11 H7 121.1 . . ?
C8 C11 H7 121.1 . . ?
C14 C12 C13 110.27(7) . . ?
C14 C12 C4 111.53(7) . . ?
C13 C12 C4 113.16(7) . . ?
C14 C12 H8 107.2 . . ?
C13 C12 H8 107.2 . . ?
C4 C12 H8 107.2 . . ?
N2 C13 C12 177.93(10) . . ?
N3 C14 C12 175.67(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 1.52(12) . . . . ?
C1 C2 C3 C4 -178.23(7) . . . . ?
C2 C3 C4 C5 -66.47(9) . . . . ?
C2 C3 C4 C9 49.75(9) . . . . ?
C2 C3 C4 C12 165.11(7) . . . . ?
C3 C4 C5 C6 -51.87(11) . . . . ?
C9 C4 C5 C6 -173.78(8) . . . . ?
C12 C4 C5 C6 73.86(11) . . . . ?
C3 C4 C5 C10 125.73(7) . . . . ?
C9 C4 C5 C10 3.82(8) . . . . ?
C12 C4 C5 C10 -108.55(7) . . . . ?
C10 C5 C6 C7 0.81(11) . . . . ?
C4 C5 C6 C7 178.16(8) . . . . ?
C5 C6 C7 C8 1.33(12) . . . . ?
C5 C6 C7 Cl1 -178.09(6) . . . . ?
C6 C7 C8 C11 -2.13(12) . . . . ?
Cl1 C7 C8 C11 177.29(6) . . . . ?
C10 N1 C9 O2 -179.05(9) . . . . ?
C10 N1 C9 C4 4.80(9) . . . . ?
C5 C4 C9 O2 178.52(8) . . . . ?
C3 C4 C9 O2 54.40(11) . . . . ?
C12 C4 C9 O2 -62.88(11) . . . . ?
C5 C4 C9 N1 -5.18(9) . . . . ?
C3 C4 C9 N1 -129.30(7) . . . . ?
C12 C4 C9 N1 113.43(7) . . . . ?
C6 C5 C10 C11 -2.22(12) . . . . ?
C4 C5 C10 C11 179.90(7) . . . . ?
C6 C5 C10 N1 176.59(7) . . . . ?
C4 C5 C10 N1 -1.29(9) . . . . ?
C9 N1 C10 C11 176.38(8) . . . . ?
C9 N1 C10 C5 -2.33(10) . . . . ?
C5 C10 C11 C8 1.40(12) . . . . ?
N1 C10 C11 C8 -177.17(8) . . . . ?
C7 C8 C11 C10 0.72(12) . . . . ?
C5 C4 C12 C14 65.19(9) . . . . ?
C3 C4 C12 C14 -165.29(7) . . . . ?
C9 C4 C12 C14 -45.30(9) . . . . ?
C5 C4 C12 C13 -59.83(9) . . . . ?
C3 C4 C12 C13 69.68(9) . . . . ?
C9 C4 C12 C13 -170.32(7) . . . . ?

_refine_diff_density_max         0.545
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.060

####################################################################### 
# 
# 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_5Aa
_database_code_depnum_ccdc_archive 'CCDC 2224166'
loop_
_audit_author_name
_audit_author_address
'Bhupendra Mali'
;National Chemical Laboratory, Pune
India
;
_audit_update_record             
;
2022-12-08 deposited with the CCDC.	2023-03-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H13 N3 O2'
_chemical_formula_sum            'C14 H13 N3 O2'
_chemical_formula_weight         255.27

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   8.7768(9)
_cell_length_b                   8.9125(9)
_cell_length_c                   15.8094(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1236.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9969
_cell_measurement_theta_min      5.70
_cell_measurement_theta_max      72.54

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.774
_shelx_estimated_absorpt_T_min   0.899
_shelx_estimated_absorpt_T_max   0.934
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.899
_exptl_absorpt_correction_T_max  0.934
_exptl_absorpt_process_details   'SADABS (Bruker, 2006)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_source_type              'Incoatech I\mS HB'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            18194
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         5.698
_diffrn_reflns_theta_max         72.536
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2428
_reflns_number_gt                2389
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.716
_reflns_Friedel_fraction_max     0.988
_reflns_Friedel_fraction_full    0.995

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

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0476P)²+0.2083P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 996 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2428
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0295
_refine_ls_R_factor_gt           0.0292
_refine_ls_wR_factor_ref         0.0762
_refine_ls_wR_factor_gt          0.0758
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.70788(14) 0.70955(14) 0.81933(7) 0.0241(3) Uani 1 1 d . . . . .
O2 O 0.39278(13) 0.80566(13) 0.60688(8) 0.0224(3) Uani 1 1 d . . . . .
N1 N 0.82530(17) 0.50257(16) 0.76126(9) 0.0200(3) Uani 1 1 d . . . . .
H1N H 0.884(3) 0.473(3) 0.8028(15) 0.030 Uiso 1 1 d . U . . .
N2 N 0.92816(16) 0.88478(16) 0.62145(9) 0.0231(3) Uani 1 1 d . . . . .
N3 N 0.54510(19) 0.99955(18) 0.57915(10) 0.0250(3) Uani 1 1 d . . . . .
H3N H 0.632(3) 1.052(3) 0.5885(15) 0.038 Uiso 1 1 d . U . . .
H4N H 0.462(3) 1.047(3) 0.5587(17) 0.038 Uiso 1 1 d . U . . .
C1 C 0.72640(18) 0.62049(18) 0.76195(10) 0.0177(3) Uani 1 1 d . . . . .
C2 C 0.64147(17) 0.62192(18) 0.67596(9) 0.0160(3) Uani 1 1 d . . . . .
C3 C 0.71694(17) 0.49285(17) 0.62992(10) 0.0158(3) Uani 1 1 d . . . . .
C4 C 0.69626(18) 0.43777(18) 0.54918(10) 0.0182(3) Uani 1 1 d . . . . .
H4 H 0.627889 0.485451 0.511137 0.022 Uiso 1 1 calc R U . . .
C5 C 0.7782(2) 0.30996(19) 0.52435(11) 0.0224(4) Uani 1 1 d . . . . .
H5 H 0.762324 0.268072 0.469794 0.027 Uiso 1 1 calc R U . . .
C6 C 0.8821(2) 0.24455(19) 0.57913(12) 0.0244(4) Uani 1 1 d . . . . .
H6 H 0.937772 0.158913 0.561081 0.029 Uiso 1 1 calc R U . . .
C7 C 0.90689(19) 0.3016(2) 0.66022(11) 0.0232(4) Uani 1 1 d . . . . .
H7 H 0.979365 0.257639 0.697315 0.028 Uiso 1 1 calc R U . . .
C8 C 0.82160(18) 0.42488(18) 0.68429(10) 0.0182(3) Uani 1 1 d . . . . .
C9 C 0.47041(18) 0.59439(19) 0.69313(10) 0.0184(3) Uani 1 1 d . . . . .
H9A H 0.453066 0.486424 0.704265 0.022 Uiso 1 1 calc R U . . .
H9B H 0.438598 0.651356 0.743904 0.022 Uiso 1 1 calc R U . . .
C10 C 0.37605(18) 0.64317(19) 0.61801(10) 0.0201(3) Uani 1 1 d . . . . .
H10 H 0.413590 0.590773 0.566105 0.024 Uiso 1 1 calc R U . . .
C11 C 0.53639(18) 0.85752(19) 0.60740(10) 0.0187(3) Uani 1 1 d . . . . .
C12 C 0.65864(18) 0.77375(18) 0.63383(10) 0.0167(3) Uani 1 1 d . . . . .
C13 C 0.80618(18) 0.83568(16) 0.62668(10) 0.0174(3) Uani 1 1 d . . . . .
C14 C 0.20778(19) 0.6130(2) 0.62859(12) 0.0268(4) Uani 1 1 d . . . . .
H14A H 0.151899 0.656705 0.580917 0.040 Uiso 1 1 calc R U . . .
H14B H 0.172141 0.658183 0.681515 0.040 Uiso 1 1 calc R U . . .
H14C H 0.190126 0.504434 0.630187 0.040 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.216(2) . ?
O2 C11 1.343(2) . ?
O2 C10 1.466(2) . ?
N1 C1 1.363(2) . ?
N1 C8 1.400(2) . ?
N1 H1N 0.87(3) . ?
N2 C13 1.159(2) . ?
N3 C11 1.345(2) . ?
N3 H3N 0.90(3) . ?
N3 H4N 0.90(3) . ?
C1 C2 1.550(2) . ?
C2 C3 1.514(2) . ?
C2 C12 1.516(2) . ?
C2 C9 1.545(2) . ?
C3 C4 1.380(2) . ?
C3 C8 1.396(2) . ?
C4 C5 1.403(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.387(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.396(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.383(2) . ?
C7 H7 0.9500 . ?
C9 C10 1.512(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C14 1.510(2) . ?
C10 H10 1.0000 . ?
C11 C12 1.372(2) . ?
C12 C13 1.412(2) . ?
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
C11 O2 C10 115.68(12) . . ?
C1 N1 C8 111.92(13) . . ?
C1 N1 H1N 126.9(15) . . ?
C8 N1 H1N 121.2(15) . . ?
C11 N3 H3N 118.4(16) . . ?
C11 N3 H4N 121.2(17) . . ?
H3N N3 H4N 120(2) . . ?
O1 C1 N1 126.46(15) . . ?
O1 C1 C2 125.75(15) . . ?
N1 C1 C2 107.79(13) . . ?
C3 C2 C12 115.06(12) . . ?
C3 C2 C9 112.88(13) . . ?
C12 C2 C9 108.39(13) . . ?
C3 C2 C1 101.83(12) . . ?
C12 C2 C1 110.17(13) . . ?
C9 C2 C1 108.17(12) . . ?
C4 C3 C8 120.11(15) . . ?
C4 C3 C2 131.12(14) . . ?
C8 C3 C2 108.76(13) . . ?
C3 C4 C5 118.71(15) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C6 C5 C4 120.25(16) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 121.51(16) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C8 C7 C6 117.26(16) . . ?
C8 C7 H7 121.4 . . ?
C6 C7 H7 121.4 . . ?
C7 C8 C3 122.10(15) . . ?
C7 C8 N1 128.27(15) . . ?
C3 C8 N1 109.61(14) . . ?
C10 C9 C2 110.40(13) . . ?
C10 C9 H9A 109.6 . . ?
C2 C9 H9A 109.6 . . ?
C10 C9 H9B 109.6 . . ?
C2 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
O2 C10 C14 106.69(14) . . ?
O2 C10 C9 108.87(13) . . ?
C14 C10 C9 113.42(14) . . ?
O2 C10 H10 109.3 . . ?
C14 C10 H10 109.3 . . ?
C9 C10 H10 109.3 . . ?
O2 C11 N3 112.05(14) . . ?
O2 C11 C12 123.27(15) . . ?
N3 C11 C12 124.68(16) . . ?
C11 C12 C13 118.68(14) . . ?
C11 C12 C2 122.80(14) . . ?
C13 C12 C2 118.38(13) . . ?
N2 C13 C12 179.01(17) . . ?
C10 C14 H14A 109.5 . . ?
C10 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C10 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C1 O1 -178.15(15) . . . . ?
C8 N1 C1 C2 1.55(18) . . . . ?
O1 C1 C2 C3 176.98(15) . . . . ?
N1 C1 C2 C3 -2.73(16) . . . . ?
O1 C1 C2 C12 54.4(2) . . . . ?
N1 C1 C2 C12 -125.27(14) . . . . ?
O1 C1 C2 C9 -63.9(2) . . . . ?
N1 C1 C2 C9 116.41(14) . . . . ?
C12 C2 C3 C4 -58.7(2) . . . . ?
C9 C2 C3 C4 66.4(2) . . . . ?
C1 C2 C3 C4 -177.85(15) . . . . ?
C12 C2 C3 C8 122.14(14) . . . . ?
C9 C2 C3 C8 -112.73(14) . . . . ?
C1 C2 C3 C8 3.00(16) . . . . ?
C8 C3 C4 C5 2.2(2) . . . . ?
C2 C3 C4 C5 -176.88(15) . . . . ?
C3 C4 C5 C6 -2.5(2) . . . . ?
C4 C5 C6 C7 0.9(3) . . . . ?
C5 C6 C7 C8 1.0(2) . . . . ?
C6 C7 C8 C3 -1.4(2) . . . . ?
C6 C7 C8 N1 -179.79(16) . . . . ?
C4 C3 C8 C7 -0.2(2) . . . . ?
C2 C3 C8 C7 179.02(14) . . . . ?
C4 C3 C8 N1 178.43(13) . . . . ?
C2 C3 C8 N1 -2.30(17) . . . . ?
C1 N1 C8 C7 179.02(16) . . . . ?
C1 N1 C8 C3 0.45(19) . . . . ?
C3 C2 C9 C10 -86.34(16) . . . . ?
C12 C2 C9 C10 42.33(17) . . . . ?
C1 C2 C9 C10 161.78(13) . . . . ?
C11 O2 C10 C14 171.68(14) . . . . ?
C11 O2 C10 C9 48.93(18) . . . . ?
C2 C9 C10 O2 -64.06(17) . . . . ?
C2 C9 C10 C14 177.33(14) . . . . ?
C10 O2 C11 N3 166.66(14) . . . . ?
C10 O2 C11 C12 -13.3(2) . . . . ?
O2 C11 C12 C13 175.95(14) . . . . ?
N3 C11 C12 C13 -4.0(2) . . . . ?
O2 C11 C12 C2 -8.4(2) . . . . ?
N3 C11 C12 C2 171.66(15) . . . . ?
C3 C2 C12 C11 119.91(16) . . . . ?
C9 C2 C12 C11 -7.5(2) . . . . ?
C1 C2 C12 C11 -125.71(16) . . . . ?
C3 C2 C12 C13 -64.43(18) . . . . ?
C9 C2 C12 C13 168.14(14) . . . . ?
C1 C2 C12 C13 49.96(18) . . . . ?

_refine_diff_density_max         0.211
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.039

####################################################################### 
# 
# 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_5Bb
_database_code_depnum_ccdc_archive 'CCDC 2224167'
loop_
_audit_author_name
_audit_author_address
'Bhupendra Mali'
;National Chemical Laboratory, Pune
India
;
_audit_update_record             
;
2022-12-08 deposited with the CCDC.	2023-03-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H19 N3 O2'
_chemical_formula_sum            'C17 H19 N3 O2'
_chemical_formula_weight         297.35

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

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

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

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

_cell_length_a                   9.9716(3)
_cell_length_b                   13.6586(4)
_cell_length_c                   11.3692(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.5400(10)
_cell_angle_gamma                90
_cell_volume                     1545.51(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9974
_cell_measurement_theta_min      5.50
_cell_measurement_theta_max      78.00

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.690
_shelx_estimated_absorpt_T_min   0.886
_shelx_estimated_absorpt_T_max   0.928
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.886
_exptl_absorpt_correction_T_max  0.928
_exptl_absorpt_process_details   'SADABS (Bruker, 2006)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_source_type              'Incoatech I\mS HB'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            55739
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_av_R_equivalents  0.0702
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         5.067
_diffrn_reflns_theta_max         79.320
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3326
_reflns_number_gt                2782
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0415P)²+1.3515P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3326
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.1171
_refine_ls_wR_factor_gt          0.1049
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.36771(11) 0.79016(8) 0.35274(9) 0.0224(2) Uani 1 1 d . . . . .
O2 O 0.55848(11) 0.92645(7) 0.66820(9) 0.0202(2) Uani 1 1 d . . . . .
N2 N 0.76680(17) 0.87099(11) 0.31287(14) 0.0336(4) Uani 1 1 d . . . . .
N1 N 0.49118(12) 0.64796(9) 0.35065(11) 0.0174(3) Uani 1 1 d . . . . .
C1 C 0.45650(14) 0.73605(10) 0.39521(12) 0.0167(3) Uani 1 1 d . . . . .
C2 C 0.54628(14) 0.75659(10) 0.50854(12) 0.0155(3) Uani 1 1 d . . . . .
N3 N 0.68686(13) 1.01393(9) 0.55319(11) 0.0206(3) Uani 1 1 d . . . . .
H3A H 0.681696 1.060842 0.605770 0.025 Uiso 1 1 calc R U . . .
H3B H 0.733062 1.023166 0.490642 0.025 Uiso 1 1 calc R U . . .
C3 C 0.63075(14) 0.66441(10) 0.51793(12) 0.0161(3) Uani 1 1 d . . . . .
C4 C 0.73065(15) 0.63555(11) 0.60005(13) 0.0204(3) Uani 1 1 d . . . . .
H4 H 0.757805 0.677002 0.664273 0.024 Uiso 1 1 calc R U . . .
C5 C 0.79134(16) 0.54387(12) 0.58693(14) 0.0243(3) Uani 1 1 d . . . . .
H5 H 0.860528 0.523130 0.642562 0.029 Uiso 1 1 calc R U . . .
C6 C 0.75117(16) 0.48323(11) 0.49338(14) 0.0236(3) Uani 1 1 d . . . . .
H6 H 0.792706 0.421081 0.486399 0.028 Uiso 1 1 calc R U . . .
C7 C 0.65089(15) 0.51184(11) 0.40936(13) 0.0209(3) Uani 1 1 d . . . . .
H7 H 0.623502 0.470627 0.344980 0.025 Uiso 1 1 calc R U . . .
C8 C 0.59310(14) 0.60271(11) 0.42380(12) 0.0171(3) Uani 1 1 d . . . . .
C9 C 0.45422(14) 0.77135(11) 0.61149(13) 0.0176(3) Uani 1 1 d . . . . .
H9A H 0.371582 0.806031 0.582251 0.021 Uiso 1 1 calc R U . . .
H9B H 0.427578 0.706611 0.641503 0.021 Uiso 1 1 calc R U . . .
C10 C 0.52298(15) 0.82955(11) 0.71129(13) 0.0190(3) Uani 1 1 d . . . . .
H10 H 0.606285 0.794591 0.741366 0.023 Uiso 1 1 calc R U . . .
C11 C 0.62379(14) 0.92765(11) 0.56851(12) 0.0168(3) Uani 1 1 d . . . . .
C12 C 0.62654(14) 0.84962(10) 0.49369(12) 0.0165(3) Uani 1 1 d . . . . .
C13 C 0.70323(16) 0.86046(10) 0.39371(14) 0.0210(3) Uani 1 1 d . . . . .
C14 C 0.43435(17) 0.84785(13) 0.81177(14) 0.0280(4) Uani 1 1 d . . . . .
H14A H 0.352185 0.881364 0.782102 0.042 Uiso 1 1 calc R U . . .
H14B H 0.482380 0.888843 0.871269 0.042 Uiso 1 1 calc R U . . .
H14C H 0.410872 0.785248 0.847253 0.042 Uiso 1 1 calc R U . . .
C15 C 0.42911(15) 0.60398(12) 0.24352(13) 0.0217(3) Uani 1 1 d . . . . .
H15A H 0.345259 0.639812 0.220509 0.026 Uiso 1 1 calc R U . . .
H15B H 0.404651 0.535378 0.260382 0.026 Uiso 1 1 calc R U . . .
C16 C 0.52035(17) 0.60522(13) 0.14026(14) 0.0265(4) Uani 1 1 d . . . . .
H16A H 0.604515 0.569945 0.163743 0.032 Uiso 1 1 calc R U . . .
H16B H 0.475297 0.569353 0.073240 0.032 Uiso 1 1 calc R U . . .
C17 C 0.55543(18) 0.70746(14) 0.09951(15) 0.0319(4) Uani 1 1 d . . . . .
H17A H 0.610932 0.702847 0.031530 0.048 Uiso 1 1 calc R U . . .
H17B H 0.605315 0.742168 0.163731 0.048 Uiso 1 1 calc R U . . .
H17C H 0.472687 0.743334 0.076977 0.048 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2289(18) . ?
O2 C11 1.3417(17) . ?
O2 C10 1.4623(17) . ?
N2 C13 1.157(2) . ?
N1 C1 1.3585(18) . ?
N1 C8 1.4150(19) . ?
N1 C15 1.4609(18) . ?
C1 C2 1.5485(19) . ?
C2 C3 1.5149(19) . ?
C2 C12 1.5166(19) . ?
C2 C9 1.5447(19) . ?
N3 C11 1.3521(19) . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?
C3 C4 1.380(2) . ?
C3 C8 1.395(2) . ?
C4 C5 1.403(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.387(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.395(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.383(2) . ?
C7 H7 0.9500 . ?
C9 C10 1.514(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C14 1.508(2) . ?
C10 H10 1.0000 . ?
C11 C12 1.365(2) . ?
C12 C13 1.416(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.529(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.519(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 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
C11 O2 C10 115.74(11) . . ?
C1 N1 C8 110.97(12) . . ?
C1 N1 C15 124.79(12) . . ?
C8 N1 C15 124.22(12) . . ?
O1 C1 N1 125.44(13) . . ?
O1 C1 C2 125.69(13) . . ?
N1 C1 C2 108.86(12) . . ?
C3 C2 C12 114.16(11) . . ?
C3 C2 C9 114.14(12) . . ?
C12 C2 C9 108.50(11) . . ?
C3 C2 C1 101.45(11) . . ?
C12 C2 C1 109.94(11) . . ?
C9 C2 C1 108.30(11) . . ?
C11 N3 H3A 120.0 . . ?
C11 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C4 C3 C8 119.69(14) . . ?
C4 C3 C2 131.30(13) . . ?
C8 C3 C2 109.01(12) . . ?
C3 C4 C5 118.76(14) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C6 C5 C4 120.56(14) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 121.22(14) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C8 C7 C6 117.16(14) . . ?
C8 C7 H7 121.4 . . ?
C6 C7 H7 121.4 . . ?
C7 C8 C3 122.61(14) . . ?
C7 C8 N1 127.73(13) . . ?
C3 C8 N1 109.66(12) . . ?
C10 C9 C2 111.93(12) . . ?
C10 C9 H9A 109.2 . . ?
C2 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
C2 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
O2 C10 C14 105.62(12) . . ?
O2 C10 C9 109.38(11) . . ?
C14 C10 C9 113.28(12) . . ?
O2 C10 H10 109.5 . . ?
C14 C10 H10 109.5 . . ?
C9 C10 H10 109.5 . . ?
O2 C11 N3 111.92(12) . . ?
O2 C11 C12 123.12(13) . . ?
N3 C11 C12 124.95(13) . . ?
C11 C12 C13 116.81(13) . . ?
C11 C12 C2 123.62(13) . . ?
C13 C12 C2 119.46(12) . . ?
N2 C13 C12 178.71(17) . . ?
C10 C14 H14A 109.5 . . ?
C10 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C10 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C15 C16 113.21(13) . . ?
N1 C15 H15A 108.9 . . ?
C16 C15 H15A 108.9 . . ?
N1 C15 H15B 108.9 . . ?
C16 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
C17 C16 C15 113.80(14) . . ?
C17 C16 H16A 108.8 . . ?
C15 C16 H16A 108.8 . . ?
C17 C16 H16B 108.8 . . ?
C15 C16 H16B 108.8 . . ?
H16A C16 H16B 107.7 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C1 O1 -177.37(14) . . . . ?
C15 N1 C1 O1 0.9(2) . . . . ?
C8 N1 C1 C2 2.20(16) . . . . ?
C15 N1 C1 C2 -179.56(13) . . . . ?
O1 C1 C2 C3 178.18(14) . . . . ?
N1 C1 C2 C3 -1.38(14) . . . . ?
O1 C1 C2 C12 -60.65(18) . . . . ?
N1 C1 C2 C12 119.79(13) . . . . ?
O1 C1 C2 C9 57.76(18) . . . . ?
N1 C1 C2 C9 -121.81(13) . . . . ?
C12 C2 C3 C4 62.2(2) . . . . ?
C9 C2 C3 C4 -63.4(2) . . . . ?
C1 C2 C3 C4 -179.59(15) . . . . ?
C12 C2 C3 C8 -118.09(13) . . . . ?
C9 C2 C3 C8 116.31(13) . . . . ?
C1 C2 C3 C8 0.09(14) . . . . ?
C8 C3 C4 C5 -0.5(2) . . . . ?
C2 C3 C4 C5 179.17(14) . . . . ?
C3 C4 C5 C6 -0.3(2) . . . . ?
C4 C5 C6 C7 0.7(2) . . . . ?
C5 C6 C7 C8 -0.3(2) . . . . ?
C6 C7 C8 C3 -0.5(2) . . . . ?
C6 C7 C8 N1 179.51(14) . . . . ?
C4 C3 C8 C7 0.9(2) . . . . ?
C2 C3 C8 C7 -178.85(13) . . . . ?
C4 C3 C8 N1 -179.10(13) . . . . ?
C2 C3 C8 N1 1.18(16) . . . . ?
C1 N1 C8 C7 177.86(14) . . . . ?
C15 N1 C8 C7 -0.4(2) . . . . ?
C1 N1 C8 C3 -2.17(16) . . . . ?
C15 N1 C8 C3 179.57(13) . . . . ?
C3 C2 C9 C10 90.46(14) . . . . ?
C12 C2 C9 C10 -38.07(16) . . . . ?
C1 C2 C9 C10 -157.38(12) . . . . ?
C11 O2 C10 C14 -171.93(12) . . . . ?
C11 O2 C10 C9 -49.69(16) . . . . ?
C2 C9 C10 O2 60.78(15) . . . . ?
C2 C9 C10 C14 178.30(13) . . . . ?
C10 O2 C11 N3 -161.84(12) . . . . ?
C10 O2 C11 C12 17.23(19) . . . . ?
O2 C11 C12 C13 -178.01(13) . . . . ?
N3 C11 C12 C13 0.9(2) . . . . ?
O2 C11 C12 C2 5.8(2) . . . . ?
N3 C11 C12 C2 -175.25(13) . . . . ?
C3 C2 C12 C11 -122.74(15) . . . . ?
C9 C2 C12 C11 5.78(19) . . . . ?
C1 C2 C12 C11 124.05(15) . . . . ?
C3 C2 C12 C13 61.17(17) . . . . ?
C9 C2 C12 C13 -170.32(13) . . . . ?
C1 C2 C12 C13 -52.04(17) . . . . ?
C1 N1 C15 C16 107.66(16) . . . . ?
C8 N1 C15 C16 -74.32(18) . . . . ?
N1 C15 C16 C17 -63.41(18) . . . . ?

_refine_diff_density_max         0.298
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.055

####################################################################### 
# 
# 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_4Ah
_database_code_depnum_ccdc_archive 'CCDC 2224165'
loop_
_audit_author_name
_audit_author_address
'Bhupendra Mali'
;National Chemical Laboratory, Pune
India
;
_audit_update_record             
;
2022-12-08 deposited with the CCDC.	2023-03-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H10 F N3 O2'
_chemical_formula_sum            'C14 H10 F N3 O2'
_chemical_formula_weight         271.25

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   10.0790(8)
_cell_length_b                   7.1417(5)
_cell_length_c                   17.9545(13)
_cell_angle_alpha                90
_cell_angle_beta                 91.403(3)
_cell_angle_gamma                90
_cell_volume                     1292.00(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9817
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      34.46

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.106
_shelx_estimated_absorpt_T_min   0.987
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.987
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_process_details   'SADABS (Bruker, 2006)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_source_type              'Incoatech I\mS HB'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            88591
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_av_R_equivalents  0.0626
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.269
_diffrn_reflns_theta_max         34.896
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             5486
_reflns_number_gt                4545
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0531P)²+0.4014P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5486
_refine_ls_number_parameters     186
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.1090
_refine_ls_wR_factor_gt          0.1019
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.33537(6) 0.90961(8) 0.18454(3) 0.02242(12) Uani 1 1 d . . . . .
O1 O 0.54679(5) 0.64263(8) 0.43090(3) 0.01345(11) Uani 1 1 d . . . . .
O2 O 0.34192(6) 1.00973(8) 0.45952(3) 0.01759(12) Uani 1 1 d . . . . .
N1 N 0.43624(6) 0.75069(10) 0.32525(4) 0.01286(12) Uani 1 1 d . . . . .
H10 H 0.5077(15) 0.772(2) 0.2971(8) 0.031(4) Uiso 1 1 d . . . . .
N2 N 0.35026(8) 0.28825(11) 0.28885(4) 0.02203(15) Uani 1 1 d . . . . .
N3 N 0.05730(8) 0.30354(11) 0.45873(5) 0.02188(15) Uani 1 1 d . . . . .
C1 C 0.11634(9) 0.87928(12) 0.22882(5) 0.01972(16) Uani 1 1 d . . . . .
H1 H 0.080939 0.929506 0.183551 0.024 Uiso 1 1 calc R U . . .
C2 C 0.03190(8) 0.82799(13) 0.28556(5) 0.01973(16) Uani 1 1 d . . . . .
H9 H -0.061025 0.846693 0.279284 0.024 Uiso 1 1 calc R U . . .
C3 C 0.08260(8) 0.74896(11) 0.35189(4) 0.01510(14) Uani 1 1 d . . . . .
H8 H 0.025097 0.714056 0.390671 0.018 Uiso 1 1 calc R U . . .
C4 C 0.21841(7) 0.72303(10) 0.35953(4) 0.01139(12) Uani 1 1 d . . . . .
C5 C 0.30271(7) 0.63705(10) 0.42120(4) 0.00969(12) Uani 1 1 d . . . . .
C6 C 0.27792(7) 0.70597(10) 0.50017(4) 0.01137(13) Uani 1 1 d . . . . .
H4 H 0.186357 0.672220 0.513744 0.014 Uiso 1 1 calc R U . . .
H5 H 0.339701 0.641029 0.535237 0.014 Uiso 1 1 calc R U . . .
C7 C 0.29588(7) 0.91523(11) 0.50894(4) 0.01318(13) Uani 1 1 d . . . . .
C8 C 0.25273(11) 0.99558(13) 0.58179(5) 0.0257(2) Uani 1 1 d . . . . .
H2 H 0.270053 1.130606 0.582585 0.039 Uiso 1 1 calc R U . . .
H7 H 0.302415 0.935355 0.622817 0.039 Uiso 1 1 calc R U . . .
H6 H 0.157588 0.973209 0.587478 0.039 Uiso 1 1 calc R U . . .
C9 C 0.30368(7) 0.77991(10) 0.30358(4) 0.01228(13) Uani 1 1 d . . . . .
C10 C 0.44533(7) 0.67921(10) 0.39560(4) 0.01064(12) Uani 1 1 d . . . . .
C11 C 0.29326(7) 0.41723(10) 0.42084(4) 0.01070(12) Uani 1 1 d . . . . .
H3 H 0.359853 0.367351 0.457978 0.013 Uiso 1 1 calc R U . . .
C12 C 0.32404(8) 0.33996(11) 0.34701(4) 0.01421(14) Uani 1 1 d . . . . .
C13 C 0.16076(8) 0.35198(11) 0.44200(4) 0.01366(13) Uani 1 1 d . . . . .
C14 C 0.25196(8) 0.85686(11) 0.23861(4) 0.01587(14) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C14 1.3532(9) . ?
O1 C10 1.2182(9) . ?
O2 C7 1.2158(9) . ?
N1 C10 1.3633(9) . ?
N1 C9 1.3981(10) . ?
N1 H10 0.903(15) . ?
N2 C12 1.1446(11) . ?
N3 C13 1.1457(11) . ?
C1 C14 1.3832(12) . ?
C1 C2 1.3924(13) . ?
C1 H1 0.9500 . ?
C2 C3 1.4030(11) . ?
C2 H9 0.9500 . ?
C3 C4 1.3848(10) . ?
C3 H8 0.9500 . ?
C4 C9 1.3981(10) . ?
C4 C5 1.5096(10) . ?
C5 C6 1.5273(10) . ?
C5 C10 1.5493(10) . ?
C5 C11 1.5728(10) . ?
C6 C7 1.5131(10) . ?
C6 H4 0.9900 . ?
C6 H5 0.9900 . ?
C7 C8 1.5024(11) . ?
C8 H2 0.9800 . ?
C8 H7 0.9800 . ?
C8 H6 0.9800 . ?
C9 C14 1.3801(10) . ?
C11 C13 1.4730(10) . ?
C11 C12 1.4759(10) . ?
C11 H3 1.0000 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 N1 C9 110.84(6) . . ?
C10 N1 H10 123.0(9) . . ?
C9 N1 H10 126.1(9) . . ?
C14 C1 C2 119.77(7) . . ?
C14 C1 H1 120.1 . . ?
C2 C1 H1 120.1 . . ?
C1 C2 C3 120.69(8) . . ?
C1 C2 H9 119.7 . . ?
C3 C2 H9 119.7 . . ?
C4 C3 C2 118.45(7) . . ?
C4 C3 H8 120.8 . . ?
C2 C3 H8 120.8 . . ?
C3 C4 C9 120.90(7) . . ?
C3 C4 C5 131.62(7) . . ?
C9 C4 C5 107.47(6) . . ?
C4 C5 C6 116.61(6) . . ?
C4 C5 C10 102.30(6) . . ?
C6 C5 C10 112.76(6) . . ?
C4 C5 C11 111.72(6) . . ?
C6 C5 C11 108.31(6) . . ?
C10 C5 C11 104.43(5) . . ?
C7 C6 C5 113.14(6) . . ?
C7 C6 H4 109.0 . . ?
C5 C6 H4 109.0 . . ?
C7 C6 H5 109.0 . . ?
C5 C6 H5 109.0 . . ?
H4 C6 H5 107.8 . . ?
O2 C7 C8 123.17(7) . . ?
O2 C7 C6 121.28(7) . . ?
C8 C7 C6 115.55(7) . . ?
C7 C8 H2 109.5 . . ?
C7 C8 H7 109.5 . . ?
H2 C8 H7 109.5 . . ?
C7 C8 H6 109.5 . . ?
H2 C8 H6 109.5 . . ?
H7 C8 H6 109.5 . . ?
C14 C9 C4 119.79(7) . . ?
C14 C9 N1 129.29(7) . . ?
C4 C9 N1 110.90(6) . . ?
O1 C10 N1 126.78(7) . . ?
O1 C10 C5 125.25(6) . . ?
N1 C10 C5 107.81(6) . . ?
C13 C11 C12 108.97(6) . . ?
C13 C11 C5 111.71(6) . . ?
C12 C11 C5 111.27(6) . . ?
C13 C11 H3 108.3 . . ?
C12 C11 H3 108.3 . . ?
C5 C11 H3 108.3 . . ?
N2 C12 C11 176.72(8) . . ?
N3 C13 C11 179.11(9) . . ?
F1 C14 C9 119.27(7) . . ?
F1 C14 C1 120.40(7) . . ?
C9 C14 C1 120.34(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C14 C1 C2 C3 -1.73(13) . . . . ?
C1 C2 C3 C4 -0.08(13) . . . . ?
C2 C3 C4 C9 2.12(12) . . . . ?
C2 C3 C4 C5 -177.45(8) . . . . ?
C3 C4 C5 C6 -49.67(11) . . . . ?
C9 C4 C5 C6 130.71(7) . . . . ?
C3 C4 C5 C10 -173.18(8) . . . . ?
C9 C4 C5 C10 7.20(7) . . . . ?
C3 C4 C5 C11 75.63(10) . . . . ?
C9 C4 C5 C11 -103.99(7) . . . . ?
C4 C5 C6 C7 -57.83(8) . . . . ?
C10 C5 C6 C7 60.11(8) . . . . ?
C11 C5 C6 C7 175.17(6) . . . . ?
C5 C6 C7 O2 -8.78(10) . . . . ?
C5 C6 C7 C8 170.96(7) . . . . ?
C3 C4 C9 C14 -2.36(12) . . . . ?
C5 C4 C9 C14 177.31(7) . . . . ?
C3 C4 C9 N1 176.28(7) . . . . ?
C5 C4 C9 N1 -4.06(8) . . . . ?
C10 N1 C9 C14 176.97(8) . . . . ?
C10 N1 C9 C4 -1.50(9) . . . . ?
C9 N1 C10 O1 -178.19(7) . . . . ?
C9 N1 C10 C5 6.24(8) . . . . ?
C4 C5 C10 O1 176.18(7) . . . . ?
C6 C5 C10 O1 50.12(10) . . . . ?
C11 C5 C10 O1 -67.25(9) . . . . ?
C4 C5 C10 N1 -8.16(7) . . . . ?
C6 C5 C10 N1 -134.22(6) . . . . ?
C11 C5 C10 N1 108.41(6) . . . . ?
C4 C5 C11 C13 -68.48(8) . . . . ?
C6 C5 C11 C13 61.29(8) . . . . ?
C10 C5 C11 C13 -178.31(6) . . . . ?
C4 C5 C11 C12 53.57(8) . . . . ?
C6 C5 C11 C12 -176.66(6) . . . . ?
C10 C5 C11 C12 -56.27(7) . . . . ?
C4 C9 C14 F1 -179.32(7) . . . . ?
N1 C9 C14 F1 2.33(13) . . . . ?
C4 C9 C14 C1 0.49(12) . . . . ?
N1 C9 C14 C1 -177.85(8) . . . . ?
C2 C1 C14 F1 -178.67(8) . . . . ?
C2 C1 C14 C9 1.52(13) . . . . ?

_refine_diff_density_max         0.509
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.055

