# Supplementary Information (SI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Compound_2a
_database_code_depnum_ccdc_archive 'CCDC 2358586'
loop_
_audit_author_name
_audit_author_address
'Mario Macias'
;Departamento de Quimica, Universidad de los Andes, Bogota
Colombia
;
_audit_update_record             
;
2024-05-27 deposited with the CCDC.	2025-01-10 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 H11 N3 O'
_chemical_formula_sum            'C14 H11 N3 O'
_chemical_formula_weight         237.26

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

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

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

_cell_length_a                   13.4786(15)
_cell_length_b                   7.2734(10)
_cell_length_c                   24.637(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2415.2(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3407
_cell_measurement_theta_min      4.8390
_cell_measurement_theta_max      76.1400

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_F_000             992
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.692
_shelx_estimated_absorpt_T_min   0.857
_shelx_estimated_absorpt_T_max   0.886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.56707
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.119a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   
'SuperNova (Cu) micro-focus sealed X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.6144
_diffrn_reflns_number            7999
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.588
_diffrn_reflns_theta_max         76.377
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2506
_reflns_number_gt                2186
_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       'CrysAlisPro 1.171.41.119a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.119a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.119a (Rigaku OD, 2021)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0775P)²+0.3202P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0011(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2506
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0467
_refine_ls_wR_factor_ref         0.1352
_refine_ls_wR_factor_gt          0.1271
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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
O11 O 0.02680(8) 0.16821(19) 0.06271(4) 0.0570(3) Uani 1 1 d . . . . .
N8 N 0.37105(8) 0.05337(17) 0.03556(5) 0.0408(3) Uani 1 1 d . . . . .
N6 N 0.41160(9) -0.06471(19) -0.05298(5) 0.0454(3) Uani 1 1 d . . . . .
H6 H 0.474975 -0.068188 -0.049076 0.054 Uiso 1 1 calc R U . . .
N5 N 0.36245(9) -0.1154(2) -0.09947(5) 0.0464(3) Uani 1 1 d . . . . .
C7 C 0.34783(10) -0.00894(19) -0.01437(5) 0.0384(3) Uani 1 1 d . . . . .
C4 C 0.26679(10) -0.0940(2) -0.08987(5) 0.0416(3) Uani 1 1 d . . . . .
C2 C 0.17145(10) 0.01761(19) -0.00326(5) 0.0391(3) Uani 1 1 d . . . . .
H2 H 0.106570 0.007210 -0.015741 0.047 Uiso 1 1 calc R U . . .
C3 C 0.25169(10) -0.02730(18) -0.03596(5) 0.0376(3) Uani 1 1 d . . . . .
C1 C 0.19234(10) 0.07906(19) 0.04916(5) 0.0383(3) Uani 1 1 d . . . . .
C10 C 0.10715(10) 0.1361(2) 0.08362(6) 0.0414(3) Uani 1 1 d . . . . .
C9 C 0.29199(10) 0.09513(19) 0.06590(5) 0.0397(3) Uani 1 1 d . . . . .
H9 H 0.303651 0.138236 0.100863 0.048 Uiso 1 1 calc R U . . .
C13 C 0.11764(10) 0.1574(2) 0.14401(6) 0.0414(3) Uani 1 1 d . . . . .
C18 C 0.17199(12) 0.0349(2) 0.17559(7) 0.0508(4) Uani 1 1 d . . . . .
H18 H 0.208309 -0.058402 0.159130 0.061 Uiso 1 1 calc R U . . .
C14 C 0.06514(12) 0.2970(2) 0.16929(7) 0.0515(4) Uani 1 1 d . . . . .
H14 H 0.027888 0.378617 0.148580 0.062 Uiso 1 1 calc R U . . .
C12 C 0.18938(11) -0.1308(3) -0.13178(6) 0.0524(4) Uani 1 1 d . . . . .
H12A H 0.158024 -0.017332 -0.141885 0.079 Uiso 1 1 calc R U . . .
H12B H 0.140605 -0.213444 -0.117265 0.079 Uiso 1 1 calc R U . . .
H12C H 0.219723 -0.185234 -0.163157 0.079 Uiso 1 1 calc R U . . .
C17 C 0.17195(14) 0.0522(3) 0.23173(7) 0.0614(5) Uani 1 1 d . . . . .
H17 H 0.207243 -0.031253 0.252820 0.074 Uiso 1 1 calc R U . . .
C16 C 0.12018(13) 0.1917(3) 0.25627(7) 0.0618(5) Uani 1 1 d . . . . .
H16 H 0.120429 0.202630 0.293883 0.074 Uiso 1 1 calc R U . . .
C15 C 0.06781(13) 0.3157(3) 0.22515(7) 0.0619(5) Uani 1 1 d . . . . .
H15 H 0.034168 0.412142 0.241744 0.074 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
O11 C10 1.2219(18) . ?
N8 C9 1.3367(17) . ?
N8 C7 1.3477(18) . ?
N6 C7 1.3447(18) . ?
N6 N5 1.3734(17) . ?
N6 H6 0.8600 . ?
N5 C4 1.3201(19) . ?
C7 C3 1.4072(18) . ?
C4 C3 1.4287(18) . ?
C4 C12 1.492(2) . ?
C2 C3 1.3875(18) . ?
C2 C1 1.3955(19) . ?
C2 H2 0.9300 . ?
C1 C9 1.4099(18) . ?
C1 C10 1.4869(18) . ?
C10 C13 1.5027(19) . ?
C9 H9 0.9300 . ?
C13 C14 1.385(2) . ?
C13 C18 1.391(2) . ?
C18 C17 1.389(2) . ?
C18 H18 0.9300 . ?
C14 C15 1.383(2) . ?
C14 H14 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C17 C16 1.372(3) . ?
C17 H17 0.9300 . ?
C16 C15 1.378(3) . ?
C16 H16 0.9300 . ?
C15 H15 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N8 C7 113.68(11) . . ?
C7 N6 N5 111.26(12) . . ?
C7 N6 H6 124.4 . . ?
N5 N6 H6 124.4 . . ?
C4 N5 N6 106.86(12) . . ?
N6 C7 N8 126.78(12) . . ?
N6 C7 C3 107.01(12) . . ?
N8 C7 C3 126.21(12) . . ?
N5 C4 C3 110.22(12) . . ?
N5 C4 C12 122.54(13) . . ?
C3 C4 C12 127.20(13) . . ?
C3 C2 C1 117.09(12) . . ?
C3 C2 H2 121.5 . . ?
C1 C2 H2 121.5 . . ?
C2 C3 C7 118.43(12) . . ?
C2 C3 C4 136.95(13) . . ?
C7 C3 C4 104.62(11) . . ?
C2 C1 C9 119.31(12) . . ?
C2 C1 C10 117.51(12) . . ?
C9 C1 C10 123.06(12) . . ?
O11 C10 C1 119.81(13) . . ?
O11 C10 C13 118.76(12) . . ?
C1 C10 C13 121.43(12) . . ?
N8 C9 C1 125.25(12) . . ?
N8 C9 H9 117.4 . . ?
C1 C9 H9 117.4 . . ?
C14 C13 C18 119.13(14) . . ?
C14 C13 C10 118.20(14) . . ?
C18 C13 C10 122.50(13) . . ?
C17 C18 C13 119.91(15) . . ?
C17 C18 H18 120.0 . . ?
C13 C18 H18 120.0 . . ?
C15 C14 C13 120.39(16) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C4 C12 H12A 109.5 . . ?
C4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C16 C17 C18 120.41(17) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C17 C16 C15 119.95(16) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C15 C14 120.16(17) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N6 N5 C4 -0.91(18) . . . . ?
N5 N6 C7 N8 -178.54(14) . . . . ?
N5 N6 C7 C3 1.28(17) . . . . ?
C9 N8 C7 N6 -178.49(14) . . . . ?
C9 N8 C7 C3 1.7(2) . . . . ?
N6 N5 C4 C3 0.16(17) . . . . ?
N6 N5 C4 C12 178.28(14) . . . . ?
C1 C2 C3 C7 0.2(2) . . . . ?
C1 C2 C3 C4 179.62(15) . . . . ?
N6 C7 C3 C2 178.45(13) . . . . ?
N8 C7 C3 C2 -1.7(2) . . . . ?
N6 C7 C3 C4 -1.11(16) . . . . ?
N8 C7 C3 C4 178.72(14) . . . . ?
N5 C4 C3 C2 -178.85(16) . . . . ?
C12 C4 C3 C2 3.1(3) . . . . ?
N5 C4 C3 C7 0.59(16) . . . . ?
C12 C4 C3 C7 -177.42(15) . . . . ?
C3 C2 C1 C9 1.0(2) . . . . ?
C3 C2 C1 C10 177.12(13) . . . . ?
C2 C1 C10 O11 -16.6(2) . . . . ?
C9 C1 C10 O11 159.41(15) . . . . ?
C2 C1 C10 C13 164.04(13) . . . . ?
C9 C1 C10 C13 -20.0(2) . . . . ?
C7 N8 C9 C1 -0.3(2) . . . . ?
C2 C1 C9 N8 -1.0(2) . . . . ?
C10 C1 C9 N8 -176.91(14) . . . . ?
O11 C10 C13 C14 -35.3(2) . . . . ?
C1 C10 C13 C14 144.08(15) . . . . ?
O11 C10 C13 C18 140.01(16) . . . . ?
C1 C10 C13 C18 -40.6(2) . . . . ?
C14 C13 C18 C17 0.9(2) . . . . ?
C10 C13 C18 C17 -174.37(15) . . . . ?
C18 C13 C14 C15 0.8(3) . . . . ?
C10 C13 C14 C15 176.28(15) . . . . ?
C13 C18 C17 C16 -1.3(3) . . . . ?
C18 C17 C16 C15 0.0(3) . . . . ?
C17 C16 C15 C14 1.7(3) . . . . ?
C13 C14 C15 C16 -2.1(3) . . . . ?

_refine_diff_density_max         0.286
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_Compound_2b_prime
_database_code_depnum_ccdc_archive 'CCDC 2358589'
loop_
_audit_author_name
_audit_author_address
'Mario Macias'
;Departamento de Quimica, Universidad de los Andes, Bogota
Colombia
;
_audit_update_record             
;
2024-05-27 deposited with the CCDC.	2025-01-10 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         'C22 H15 Cl2 N3 O'
_chemical_formula_sum            'C22 H15 Cl2 N3 O'
_chemical_formula_weight         408.27

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'
Cl Cl 0.3639 0.7018 '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/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                   7.0670(7)
_cell_length_b                   23.637(3)
_cell_length_c                   11.1905(12)
_cell_angle_alpha                90
_cell_angle_beta                 93.717(9)
_cell_angle_gamma                90
_cell_volume                     1865.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4035
_cell_measurement_theta_min      3.8120
_cell_measurement_theta_max      76.0580

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    3.279
_shelx_estimated_absorpt_T_min   0.532
_shelx_estimated_absorpt_T_max   0.575
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.67885
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.119a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   
'SuperNova (Cu) micro-focus sealed X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.6144
_diffrn_reflns_number            9511
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.740
_diffrn_reflns_theta_max         76.462
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3799
_reflns_number_gt                3041
_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       'CrysAlisPro 1.171.41.119a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.119a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.119a (Rigaku OD, 2021)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0617P)²+0.2378P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3799
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1246
_refine_ls_wR_factor_gt          0.1128
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.002
_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
Cl28 Cl 0.39488(10) 0.68426(3) 0.17110(6) 0.0801(2) Uani 1 1 d . . . . .
Cl16 Cl 0.09111(9) 1.23202(3) 1.19144(5) 0.0725(2) Uani 1 1 d . . . . .
N1 N 0.2345(2) 1.05225(7) 0.73029(13) 0.0467(4) Uani 1 1 d . . . . .
C23 C 0.2478(3) 0.84605(10) 0.13895(18) 0.0551(5) Uani 1 1 d . . . . .
H23 H 0.192403 0.869521 0.079839 0.066 Uiso 1 1 calc R U . . .
C15 C 0.2578(3) 1.14831(9) 0.90767(17) 0.0517(5) Uani 1 1 d . . . . .
H15 H 0.308708 1.157155 0.835397 0.062 Uiso 1 1 calc R U . . .
C24 C 0.2757(3) 0.78974(10) 0.11330(19) 0.0588(5) Uani 1 1 d . . . . .
H24 H 0.237770 0.775060 0.038430 0.071 Uiso 1 1 calc R U . . .
N5 N 0.3189(3) 0.95652(8) 0.68751(16) 0.0580(4) Uani 1 1 d . . . . .
N9 N 0.1771(2) 1.10097(7) 0.67326(14) 0.0503(4) Uani 1 1 d . . . . .
C14 C 0.2221(3) 1.19114(9) 0.98731(18) 0.0546(5) Uani 1 1 d . . . . .
H14 H 0.249770 1.228503 0.969097 0.065 Uiso 1 1 calc R U . . .
C13 C 0.1450(3) 1.17793(10) 1.09429(17) 0.0547(5) Uani 1 1 d . . . . .
C25 C 0.3610(3) 0.75563(10) 0.20117(19) 0.0553(5) Uani 1 1 d . . . . .
C2 C 0.2541(3) 1.04488(9) 0.85213(17) 0.0485(4) Uani 1 1 d . . . . .
C10 C 0.2186(3) 1.09214(9) 0.93412(16) 0.0480(4) Uani 1 1 d . . . . .
C19 C 0.2636(3) 0.92975(9) 0.27323(17) 0.0518(5) Uani 1 1 d . . . . .
C26 C 0.4173(3) 0.77662(10) 0.31277(19) 0.0598(5) Uani 1 1 d . . . . .
H26 H 0.475564 0.753144 0.370818 0.072 Uiso 1 1 calc R U . . .
C22 C 0.3003(2) 0.86867(9) 0.25098(16) 0.0477(4) Uani 1 1 d . . . . .
C3 C 0.3070(3) 0.99154(9) 0.88925(18) 0.0578(5) Uani 1 1 d . . . . .
H3 H 0.321808 0.983308 0.970586 0.069 Uiso 1 1 calc R U . . .
C17 C 0.2340(3) 1.00491(9) 0.42028(17) 0.0506(4) Uani 1 1 d . . . . .
H17 H 0.208116 1.028108 0.354110 0.061 Uiso 1 1 calc R U . . .
C4 C 0.3387(3) 0.94958(10) 0.8049(2) 0.0622(5) Uani 1 1 d . . . . .
H4 H 0.376587 0.914126 0.833473 0.075 Uiso 1 1 calc R U . . .
C8 C 0.1741(3) 1.08783(9) 0.55696(17) 0.0494(4) Uani 1 1 d . . . . .
C27 C 0.3858(3) 0.83307(10) 0.33727(17) 0.0546(5) Uani 1 1 d . . . . .
H27 H 0.422422 0.847417 0.412633 0.066 Uiso 1 1 calc R U . . .
C21 C 0.1133(4) 1.13198(10) 0.46722(19) 0.0671(6) Uani 1 1 d . . . . .
H21A H 0.004009 1.118871 0.419721 0.101 Uiso 1 1 calc R U . . .
H21B H 0.214585 1.139333 0.416213 0.101 Uiso 1 1 calc R U . . .
H21C H 0.082092 1.166133 0.507995 0.101 Uiso 1 1 calc R U . . .
C11 C 0.1444(3) 1.07974(10) 1.04427(17) 0.0565(5) Uani 1 1 d . . . . .
H11 H 0.120253 1.042356 1.064291 0.068 Uiso 1 1 calc R U . . .
C18 C 0.2722(3) 0.95107(9) 0.39674(17) 0.0515(4) Uani 1 1 d . . . . .
H18 H 0.304862 0.926495 0.459634 0.062 Uiso 1 1 calc R U . . .
C6 C 0.2652(3) 1.00838(8) 0.65003(17) 0.0473(4) Uani 1 1 d . . . . .
C12 C 0.1066(3) 1.12257(10) 1.12342(17) 0.0592(5) Uani 1 1 d . . . . .
H12 H 0.055626 1.114114 1.195870 0.071 Uiso 1 1 calc R U . . .
C7 C 0.2278(3) 1.03173(9) 0.53568(17) 0.0485(4) Uani 1 1 d . . . . .
O7 O 0.2237(3) 0.96093(7) 0.18721(13) 0.0729(5) 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
Cl28 C25 1.740(2) . ?
Cl16 C13 1.736(2) . ?
N1 N9 1.366(2) . ?
N1 C2 1.373(2) . ?
N1 C6 1.398(2) . ?
C23 C24 1.379(3) . ?
C23 C22 1.391(3) . ?
C23 H23 0.9300 . ?
C15 C14 1.383(3) . ?
C15 C10 1.392(3) . ?
C15 H15 0.9300 . ?
C24 C25 1.380(3) . ?
C24 H24 0.9300 . ?
N5 C4 1.322(3) . ?
N5 C6 1.342(3) . ?
N9 C8 1.337(2) . ?
C14 C13 1.383(3) . ?
C14 H14 0.9300 . ?
C13 C12 1.380(3) . ?
C25 C26 1.378(3) . ?
C2 C3 1.372(3) . ?
C2 C10 1.477(3) . ?
C10 C11 1.402(3) . ?
C19 O7 1.230(2) . ?
C19 C18 1.469(3) . ?
C19 C22 1.491(3) . ?
C26 C27 1.383(3) . ?
C26 H26 0.9300 . ?
C22 C27 1.389(3) . ?
C3 C4 1.397(3) . ?
C3 H3 0.9300 . ?
C17 C18 1.331(3) . ?
C17 C7 1.442(3) . ?
C17 H17 0.9300 . ?
C4 H4 0.9300 . ?
C8 C7 1.404(3) . ?
C8 C21 1.492(3) . ?
C27 H27 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C11 C12 1.382(3) . ?
C11 H11 0.9300 . ?
C18 H18 0.9300 . ?
C6 C7 1.403(3) . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N9 N1 C2 125.38(16) . . ?
N9 N1 C6 112.29(15) . . ?
C2 N1 C6 122.28(17) . . ?
C24 C23 C22 121.7(2) . . ?
C24 C23 H23 119.2 . . ?
C22 C23 H23 119.2 . . ?
C14 C15 C10 120.94(18) . . ?
C14 C15 H15 119.5 . . ?
C10 C15 H15 119.5 . . ?
C23 C24 C25 118.5(2) . . ?
C23 C24 H24 120.7 . . ?
C25 C24 H24 120.7 . . ?
C4 N5 C6 115.68(18) . . ?
C8 N9 N1 104.14(16) . . ?
C15 C14 C13 119.4(2) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C12 C13 C14 120.9(2) . . ?
C12 C13 Cl16 119.74(15) . . ?
C14 C13 Cl16 119.37(18) . . ?
C26 C25 C24 121.5(2) . . ?
C26 C25 Cl28 119.28(18) . . ?
C24 C25 Cl28 119.21(17) . . ?
C3 C2 N1 115.18(18) . . ?
C3 C2 C10 124.11(18) . . ?
N1 C2 C10 120.71(18) . . ?
C15 C10 C11 118.52(18) . . ?
C15 C10 C2 123.03(17) . . ?
C11 C10 C2 118.44(18) . . ?
O7 C19 C18 121.6(2) . . ?
O7 C19 C22 118.88(18) . . ?
C18 C19 C22 119.50(18) . . ?
C25 C26 C27 119.1(2) . . ?
C25 C26 H26 120.5 . . ?
C27 C26 H26 120.5 . . ?
C27 C22 C23 118.18(19) . . ?
C27 C22 C19 122.89(18) . . ?
C23 C22 C19 118.92(18) . . ?
C2 C3 C4 120.03(19) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C18 C17 C7 128.0(2) . . ?
C18 C17 H17 116.0 . . ?
C7 C17 H17 116.0 . . ?
N5 C4 C3 124.9(2) . . ?
N5 C4 H4 117.6 . . ?
C3 C4 H4 117.6 . . ?
N9 C8 C7 113.41(18) . . ?
N9 C8 C21 118.57(19) . . ?
C7 C8 C21 128.01(18) . . ?
C26 C27 C22 120.99(19) . . ?
C26 C27 H27 119.5 . . ?
C22 C27 H27 119.5 . . ?
C8 C21 H21A 109.5 . . ?
C8 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C8 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C12 C11 C10 120.6(2) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C17 C18 C19 121.18(19) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 H18 119.4 . . ?
N5 C6 N1 121.95(17) . . ?
N5 C6 C7 132.61(18) . . ?
N1 C6 C7 105.44(17) . . ?
C13 C12 C11 119.61(18) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C6 C7 C8 104.71(17) . . ?
C6 C7 C17 129.0(2) . . ?
C8 C7 C17 126.26(19) . . ?

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
C22 C23 C24 C25 -1.1(3) . . . . ?
C2 N1 N9 C8 -178.29(16) . . . . ?
C6 N1 N9 C8 -0.8(2) . . . . ?
C10 C15 C14 C13 -0.5(3) . . . . ?
C15 C14 C13 C12 1.2(3) . . . . ?
C15 C14 C13 Cl16 -177.35(16) . . . . ?
C23 C24 C25 C26 0.3(3) . . . . ?
C23 C24 C25 Cl28 179.24(16) . . . . ?
N9 N1 C2 C3 177.68(17) . . . . ?
C6 N1 C2 C3 0.4(3) . . . . ?
N9 N1 C2 C10 -2.1(3) . . . . ?
C6 N1 C2 C10 -179.44(16) . . . . ?
C14 C15 C10 C11 -0.8(3) . . . . ?
C14 C15 C10 C2 179.98(19) . . . . ?
C3 C2 C10 C15 146.9(2) . . . . ?
N1 C2 C10 C15 -33.3(3) . . . . ?
C3 C2 C10 C11 -32.3(3) . . . . ?
N1 C2 C10 C11 147.48(19) . . . . ?
C24 C25 C26 C27 0.5(3) . . . . ?
Cl28 C25 C26 C27 -178.41(16) . . . . ?
C24 C23 C22 C27 1.1(3) . . . . ?
C24 C23 C22 C19 -179.14(18) . . . . ?
O7 C19 C22 C27 165.4(2) . . . . ?
C18 C19 C22 C27 -15.7(3) . . . . ?
O7 C19 C22 C23 -14.3(3) . . . . ?
C18 C19 C22 C23 164.52(18) . . . . ?
N1 C2 C3 C4 0.6(3) . . . . ?
C10 C2 C3 C4 -179.55(19) . . . . ?
C6 N5 C4 C3 0.4(3) . . . . ?
C2 C3 C4 N5 -1.1(4) . . . . ?
N1 N9 C8 C7 0.1(2) . . . . ?
N1 N9 C8 C21 178.97(17) . . . . ?
C25 C26 C27 C22 -0.6(3) . . . . ?
C23 C22 C27 C26 -0.2(3) . . . . ?
C19 C22 C27 C26 -179.98(18) . . . . ?
C15 C10 C11 C12 1.6(3) . . . . ?
C2 C10 C11 C12 -179.21(19) . . . . ?
C7 C17 C18 C19 177.00(18) . . . . ?
O7 C19 C18 C17 1.1(3) . . . . ?
C22 C19 C18 C17 -177.73(18) . . . . ?
C4 N5 C6 N1 0.7(3) . . . . ?
C4 N5 C6 C7 -179.1(2) . . . . ?
N9 N1 C6 N5 -178.72(16) . . . . ?
C2 N1 C6 N5 -1.1(3) . . . . ?
N9 N1 C6 C7 1.1(2) . . . . ?
C2 N1 C6 C7 178.75(16) . . . . ?
C14 C13 C12 C11 -0.5(3) . . . . ?
Cl16 C13 C12 C11 178.07(17) . . . . ?
C10 C11 C12 C13 -0.9(3) . . . . ?
N5 C6 C7 C8 178.8(2) . . . . ?
N1 C6 C7 C8 -1.00(19) . . . . ?
N5 C6 C7 C17 1.1(3) . . . . ?
N1 C6 C7 C17 -178.70(17) . . . . ?
N9 C8 C7 C6 0.6(2) . . . . ?
C21 C8 C7 C6 -178.2(2) . . . . ?
N9 C8 C7 C17 178.39(17) . . . . ?
C21 C8 C7 C17 -0.4(3) . . . . ?
C18 C17 C7 C6 2.0(3) . . . . ?
C18 C17 C7 C8 -175.27(19) . . . . ?

_refine_diff_density_max         0.151
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.043

####################################################################### 
# 
# 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_Compound_3a
_database_code_depnum_ccdc_archive 'CCDC 2358588'
loop_
_audit_author_name
_audit_author_address
'Mario Macias'
;Departamento de Quimica, Universidad de los Andes, Bogota
Colombia
;
_audit_update_record             
;
2024-05-27 deposited with the CCDC.	2025-01-10 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         'C15 H13 N3 O'
_chemical_formula_sum            'C15 H13 N3 O'
_chemical_formula_weight         251.28

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      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                   6.9160(8)
_cell_length_b                   8.9551(8)
_cell_length_c                   10.3411(6)
_cell_angle_alpha                95.113(6)
_cell_angle_beta                 98.415(8)
_cell_angle_gamma                90.754(8)
_cell_volume                     630.82(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4298
_cell_measurement_theta_min      4.3430
_cell_measurement_theta_max      75.9840

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_F_000             264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.691
_shelx_estimated_absorpt_T_min   0.863
_shelx_estimated_absorpt_T_max   0.886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.87324
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.119a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   
'SuperNova (Cu) micro-focus sealed X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.6144
_diffrn_reflns_number            7396
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.340
_diffrn_reflns_theta_max         76.567
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2594
_reflns_number_gt                2259
_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       'CrysAlisPro 1.171.41.119a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.119a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.119a (Rigaku OD, 2021)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0715P)²+0.1393P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2594
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0496
_refine_ls_wR_factor_ref         0.1429
_refine_ls_wR_factor_gt          0.1358
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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
N8 N 0.24331(19) 0.18619(14) 0.42375(13) 0.0466(3) Uani 1 1 d . . . . .
N6 N 0.2308(2) -0.04692(14) 0.28943(13) 0.0473(3) Uani 1 1 d . . . . .
C7 C 0.24033(19) 0.03606(16) 0.40551(15) 0.0411(3) Uani 1 1 d . . . . .
N5 N 0.2304(2) -0.19731(14) 0.30615(14) 0.0502(3) Uani 1 1 d . . . . .
C3 C 0.2463(2) -0.06464(15) 0.50345(15) 0.0420(3) Uani 1 1 d . . . . .
O11 O 0.2314(3) 0.14481(15) 0.88072(13) 0.0768(4) Uani 1 1 d . . . . .
C1 C 0.2563(2) 0.15034(16) 0.65624(15) 0.0435(3) Uani 1 1 d . . . . .
C2 C 0.2527(2) -0.00469(16) 0.63244(15) 0.0438(3) Uani 1 1 d . . . . .
H2 H 0.254455 -0.066154 0.700482 0.053 Uiso 1 1 calc R U . . .
C9 C 0.2518(2) 0.23835(16) 0.54897(16) 0.0460(3) Uani 1 1 d . . . . .
H9 H 0.254984 0.341959 0.567663 0.055 Uiso 1 1 calc R U . . .
C4 C 0.2398(2) -0.20941(17) 0.43317(17) 0.0470(4) Uani 1 1 d . . . . .
C10 C 0.2544(2) 0.22090(18) 0.79177(16) 0.0506(4) Uani 1 1 d . . . . .
C14 C 0.2784(2) 0.38799(18) 0.81847(15) 0.0497(4) Uani 1 1 d . . . . .
C18 C 0.4816(3) 0.6102(2) 0.8457(2) 0.0714(5) Uani 1 1 d . . . . .
H18 H 0.602180 0.656508 0.843631 0.086 Uiso 1 1 calc R U . . .
C15 C 0.1264(3) 0.4719(2) 0.8550(2) 0.0700(5) Uani 1 1 d . . . . .
H15 H 0.006493 0.425778 0.859330 0.084 Uiso 1 1 calc R U . . .
C12 C 0.2250(3) 0.0032(2) 0.15959(17) 0.0635(5) Uani 1 1 d . . . . .
H12A H 0.207805 0.109648 0.163880 0.095 Uiso 1 1 calc R U . . .
H12B H 0.118001 -0.046521 0.101408 0.095 Uiso 1 1 calc R U . . .
H12C H 0.345466 -0.020252 0.127439 0.095 Uiso 1 1 calc R U . . .
C19 C 0.4563(3) 0.4584(2) 0.81295(19) 0.0612(5) Uani 1 1 d . . . . .
H19 H 0.558827 0.402730 0.786998 0.073 Uiso 1 1 calc R U . . .
C13 C 0.2444(3) -0.35861(18) 0.4867(2) 0.0612(5) Uani 1 1 d . . . . .
H13A H 0.214832 -0.435977 0.415740 0.092 Uiso 1 1 calc R U . . .
H13B H 0.149133 -0.362792 0.545196 0.092 Uiso 1 1 calc R U . . .
H13C H 0.372121 -0.373203 0.533554 0.092 Uiso 1 1 calc R U . . .
C17 C 0.3295(4) 0.6943(2) 0.88155(19) 0.0728(6) Uani 1 1 d . . . . .
H17 H 0.346608 0.797101 0.903133 0.087 Uiso 1 1 calc R U . . .
C16 C 0.1532(4) 0.6254(2) 0.8852(2) 0.0814(6) Uani 1 1 d . . . . .
H16 H 0.049815 0.682254 0.908187 0.098 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
N8 C9 1.330(2) . ?
N8 C7 1.3403(19) . ?
N6 C7 1.347(2) . ?
N6 N5 1.3730(18) . ?
N6 C12 1.449(2) . ?
C7 C3 1.412(2) . ?
N5 C4 1.320(2) . ?
C3 C2 1.387(2) . ?
C3 C4 1.425(2) . ?
O11 C10 1.219(2) . ?
C1 C2 1.387(2) . ?
C1 C9 1.414(2) . ?
C1 C10 1.487(2) . ?
C4 C13 1.490(2) . ?
C10 C14 1.500(2) . ?
C14 C15 1.378(3) . ?
C14 C19 1.386(2) . ?
C18 C19 1.374(3) . ?
C18 C17 1.377(3) . ?
C15 C16 1.386(3) . ?
C17 C16 1.366(3) . ?

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 N8 C7 113.27(13) . . ?
C7 N6 N5 110.93(13) . . ?
C7 N6 C12 128.70(14) . . ?
N5 N6 C12 120.36(14) . . ?
N8 C7 N6 126.11(14) . . ?
N8 C7 C3 126.72(14) . . ?
N6 C7 C3 107.17(13) . . ?
C4 N5 N6 107.08(13) . . ?
C2 C3 C7 117.80(13) . . ?
C2 C3 C4 137.77(14) . . ?
C7 C3 C4 104.42(14) . . ?
C2 C1 C9 118.83(14) . . ?
C2 C1 C10 119.94(14) . . ?
C9 C1 C10 121.15(14) . . ?
C3 C2 C1 117.56(13) . . ?
N8 C9 C1 125.81(14) . . ?
N5 C4 C3 110.40(14) . . ?
N5 C4 C13 121.42(15) . . ?
C3 C4 C13 128.18(16) . . ?
O11 C10 C1 120.84(15) . . ?
O11 C10 C14 119.81(15) . . ?
C1 C10 C14 119.35(14) . . ?
C15 C14 C19 119.44(16) . . ?
C15 C14 C10 120.12(16) . . ?
C19 C14 C10 120.36(15) . . ?
C19 C18 C17 120.35(19) . . ?
C14 C15 C16 119.59(19) . . ?
C18 C19 C14 120.23(18) . . ?
C16 C17 C18 119.50(18) . . ?
C17 C16 C15 120.9(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 N8 C7 N6 179.56(14) . . . . ?
C9 N8 C7 C3 -0.4(2) . . . . ?
N5 N6 C7 N8 -179.99(13) . . . . ?
C12 N6 C7 N8 1.1(3) . . . . ?
N5 N6 C7 C3 -0.05(16) . . . . ?
C12 N6 C7 C3 -178.92(15) . . . . ?
C7 N6 N5 C4 -0.05(17) . . . . ?
C12 N6 N5 C4 178.93(15) . . . . ?
N8 C7 C3 C2 1.1(2) . . . . ?
N6 C7 C3 C2 -178.79(12) . . . . ?
N8 C7 C3 C4 -179.95(14) . . . . ?
N6 C7 C3 C4 0.12(15) . . . . ?
C7 C3 C2 C1 -1.1(2) . . . . ?
C4 C3 C2 C1 -179.56(16) . . . . ?
C9 C1 C2 C3 0.5(2) . . . . ?
C10 C1 C2 C3 177.30(13) . . . . ?
C7 N8 C9 C1 -0.4(2) . . . . ?
C2 C1 C9 N8 0.3(2) . . . . ?
C10 C1 C9 N8 -176.46(14) . . . . ?
N6 N5 C4 C3 0.12(17) . . . . ?
N6 N5 C4 C13 -179.30(14) . . . . ?
C2 C3 C4 N5 178.42(16) . . . . ?
C7 C3 C4 N5 -0.15(16) . . . . ?
C2 C3 C4 C13 -2.2(3) . . . . ?
C7 C3 C4 C13 179.22(15) . . . . ?
C2 C1 C10 O11 -6.8(2) . . . . ?
C9 C1 C10 O11 169.91(16) . . . . ?
C2 C1 C10 C14 173.98(14) . . . . ?
C9 C1 C10 C14 -9.3(2) . . . . ?
O11 C10 C14 C15 -65.4(2) . . . . ?
C1 C10 C14 C15 113.83(19) . . . . ?
O11 C10 C14 C19 111.4(2) . . . . ?
C1 C10 C14 C19 -69.3(2) . . . . ?
C19 C14 C15 C16 0.2(3) . . . . ?
C10 C14 C15 C16 177.09(19) . . . . ?
C17 C18 C19 C14 -1.4(3) . . . . ?
C15 C14 C19 C18 1.1(3) . . . . ?
C10 C14 C19 C18 -175.79(17) . . . . ?
C19 C18 C17 C16 0.4(3) . . . . ?
C18 C17 C16 C15 0.9(4) . . . . ?
C14 C15 C16 C17 -1.2(4) . . . . ?

_refine_diff_density_max         0.248
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_Compound_2b
_database_code_depnum_ccdc_archive 'CCDC 2358587'
loop_
_audit_author_name
_audit_author_address
'Mario Macias'
;Departamento de Quimica, Universidad de los Andes, Bogota
Colombia
;
_audit_update_record             
;
2024-05-27 deposited with the CCDC.	2025-01-10 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 O'
_chemical_formula_sum            'C14 H10 Cl N3 O'
_chemical_formula_weight         271.70

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
Cl Cl 0.3639 0.7018 '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      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                   6.1624(4)
_cell_length_b                   9.2368(9)
_cell_length_c                   11.2678(9)
_cell_angle_alpha                89.961(7)
_cell_angle_beta                 81.987(6)
_cell_angle_gamma                79.955(7)
_cell_volume                     625.19(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4035
_cell_measurement_theta_min      3.8120
_cell_measurement_theta_max      76.0580

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_F_000             280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    2.664
_shelx_estimated_absorpt_T_min   0.605
_shelx_estimated_absorpt_T_max   0.646
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.67885
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.119a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   
'SuperNova (Cu) micro-focus sealed X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.6144
_diffrn_reflns_number            6224
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.963
_diffrn_reflns_theta_max         76.324
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2574
_reflns_number_gt                2295
_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       'CrysAlisPro 1.171.41.119a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.119a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.119a (Rigaku OD, 2021)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0763P)²+0.1270P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2574
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0469
_refine_ls_wR_factor_ref         0.1327
_refine_ls_wR_factor_gt          0.1262
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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
Cl19 Cl -0.23795(9) 0.49140(6) 0.75937(4) 0.0663(2) Uani 1 1 d . . . . .
N5 N 0.4266(2) -0.25968(17) -0.02682(13) 0.0482(4) Uani 1 1 d . . . . .
N6 N 0.2477(2) -0.14743(17) -0.00246(13) 0.0470(3) Uani 1 1 d . . . . .
H6 H 0.138397 -0.131362 -0.043391 0.056 Uiso 1 1 calc R U . . .
N8 N 0.1193(2) 0.05279(17) 0.14056(13) 0.0453(3) Uani 1 1 d . . . . .
C1 C 0.3762(3) 0.06335(18) 0.28461(14) 0.0414(3) Uani 1 1 d . . . . .
O11 O 0.6351(2) 0.1370(2) 0.39545(17) 0.0799(6) Uani 1 1 d . . . . .
C3 C 0.4654(3) -0.12744(18) 0.13529(14) 0.0395(3) Uani 1 1 d . . . . .
C2 C 0.5239(3) -0.05857(19) 0.23266(14) 0.0416(3) Uani 1 1 d . . . . .
H2 H 0.656862 -0.092686 0.261997 0.050 Uiso 1 1 calc R U . . .
C14 C 0.0586(3) 0.19166(19) 0.50842(16) 0.0459(4) Uani 1 1 d . . . . .
H14 H 0.021212 0.112693 0.469468 0.055 Uiso 1 1 calc R U . . .
C7 C 0.2647(3) -0.06552(18) 0.09369(14) 0.0396(3) Uani 1 1 d . . . . .
C13 C 0.2660(3) 0.23059(18) 0.47593(14) 0.0414(3) Uani 1 1 d . . . . .
C9 C 0.1781(3) 0.11327(19) 0.23589(15) 0.0443(4) Uani 1 1 d . . . . .
H9 H 0.081521 0.194278 0.273045 0.053 Uiso 1 1 calc R U . . .
C10 C 0.4399(3) 0.1439(2) 0.38536(16) 0.0477(4) Uani 1 1 d . . . . .
C4 C 0.5569(3) -0.2495(2) 0.05524(14) 0.0445(4) Uani 1 1 d . . . . .
C17 C 0.1633(3) 0.4323(2) 0.62121(16) 0.0494(4) Uani 1 1 d . . . . .
H17 H 0.197067 0.513861 0.658282 0.059 Uiso 1 1 calc R U . . .
C15 C -0.0929(3) 0.2691(2) 0.59808(16) 0.0498(4) Uani 1 1 d . . . . .
H15 H -0.229081 0.239900 0.621776 0.060 Uiso 1 1 calc R U . . .
C18 C 0.3167(3) 0.3511(2) 0.53407(16) 0.0457(4) Uani 1 1 d . . . . .
H18 H 0.455951 0.377286 0.513950 0.055 Uiso 1 1 calc R U . . .
C16 C -0.0411(3) 0.3898(2) 0.65210(15) 0.0473(4) Uani 1 1 d . . . . .
C12 C 0.7660(3) -0.3569(3) 0.05766(19) 0.0613(5) Uani 1 1 d . . . . .
H12A H 0.842387 -0.375873 -0.022520 0.092 Uiso 1 1 calc R U . . .
H12B H 0.731080 -0.446924 0.091337 0.092 Uiso 1 1 calc R U . . .
H12C H 0.859528 -0.317116 0.105730 0.092 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
Cl19 C16 1.7347(18) . ?
N5 C4 1.320(2) . ?
N5 N6 1.373(2) . ?
N6 C7 1.348(2) . ?
N6 H6 0.8600 . ?
N8 C9 1.333(2) . ?
N8 C7 1.343(2) . ?
C1 C2 1.391(2) . ?
C1 C9 1.412(2) . ?
C1 C10 1.491(2) . ?
O11 C10 1.215(2) . ?
C3 C2 1.389(2) . ?
C3 C7 1.411(2) . ?
C3 C4 1.428(2) . ?
C2 H2 0.9300 . ?
C14 C15 1.382(3) . ?
C14 C13 1.388(3) . ?
C14 H14 0.9300 . ?
C13 C18 1.394(2) . ?
C13 C10 1.492(2) . ?
C9 H9 0.9300 . ?
C4 C12 1.486(2) . ?
C17 C16 1.383(3) . ?
C17 C18 1.384(3) . ?
C17 H17 0.9300 . ?
C15 C16 1.376(3) . ?
C15 H15 0.9300 . ?
C18 H18 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N5 N6 106.61(14) . . ?
C7 N6 N5 111.49(13) . . ?
C7 N6 H6 124.3 . . ?
N5 N6 H6 124.3 . . ?
C9 N8 C7 114.04(13) . . ?
C2 C1 C9 119.47(14) . . ?
C2 C1 C10 118.60(14) . . ?
C9 C1 C10 121.79(15) . . ?
C2 C3 C7 117.66(15) . . ?
C2 C3 C4 137.91(15) . . ?
C7 C3 C4 104.39(14) . . ?
C3 C2 C1 117.48(14) . . ?
C3 C2 H2 121.3 . . ?
C1 C2 H2 121.3 . . ?
C15 C14 C13 120.63(16) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
N8 C7 N6 126.65(14) . . ?
N8 C7 C3 126.52(14) . . ?
N6 C7 C3 106.84(14) . . ?
C14 C13 C18 118.63(16) . . ?
C14 C13 C10 122.31(15) . . ?
C18 C13 C10 118.99(15) . . ?
N8 C9 C1 124.80(15) . . ?
N8 C9 H9 117.6 . . ?
C1 C9 H9 117.6 . . ?
O11 C10 C1 119.87(16) . . ?
O11 C10 C13 119.40(16) . . ?
C1 C10 C13 120.71(14) . . ?
N5 C4 C3 110.67(15) . . ?
N5 C4 C12 121.24(16) . . ?
C3 C4 C12 128.09(16) . . ?
C16 C17 C18 118.71(16) . . ?
C16 C17 H17 120.6 . . ?
C18 C17 H17 120.6 . . ?
C16 C15 C14 119.62(17) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C17 C18 C13 121.15(16) . . ?
C17 C18 H18 119.4 . . ?
C13 C18 H18 119.4 . . ?
C15 C16 C17 121.20(17) . . ?
C15 C16 Cl19 119.18(14) . . ?
C17 C16 Cl19 119.61(14) . . ?
C4 C12 H12A 109.5 . . ?
C4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
C4 N5 N6 C7 0.6(2) . . . . ?
C7 C3 C2 C1 2.2(2) . . . . ?
C4 C3 C2 C1 179.64(19) . . . . ?
C9 C1 C2 C3 -1.2(2) . . . . ?
C10 C1 C2 C3 -176.98(15) . . . . ?
C9 N8 C7 N6 -179.81(17) . . . . ?
C9 N8 C7 C3 -0.2(3) . . . . ?
N5 N6 C7 N8 179.43(16) . . . . ?
N5 N6 C7 C3 -0.2(2) . . . . ?
C2 C3 C7 N8 -1.6(3) . . . . ?
C4 C3 C7 N8 -179.83(16) . . . . ?
C2 C3 C7 N6 178.01(15) . . . . ?
C4 C3 C7 N6 -0.19(18) . . . . ?
C15 C14 C13 C18 -1.2(3) . . . . ?
C15 C14 C13 C10 175.87(16) . . . . ?
C7 N8 C9 C1 1.5(3) . . . . ?
C2 C1 C9 N8 -0.8(3) . . . . ?
C10 C1 C9 N8 174.88(17) . . . . ?
C2 C1 C10 O11 24.2(3) . . . . ?
C9 C1 C10 O11 -151.5(2) . . . . ?
C2 C1 C10 C13 -154.44(17) . . . . ?
C9 C1 C10 C13 29.9(3) . . . . ?
C14 C13 C10 O11 -147.8(2) . . . . ?
C18 C13 C10 O11 29.2(3) . . . . ?
C14 C13 C10 C1 30.8(3) . . . . ?
C18 C13 C10 C1 -152.18(17) . . . . ?
N6 N5 C4 C3 -0.7(2) . . . . ?
N6 N5 C4 C12 178.65(18) . . . . ?
C2 C3 C4 N5 -177.07(19) . . . . ?
C7 C3 C4 N5 0.6(2) . . . . ?
C2 C3 C4 C12 3.7(4) . . . . ?
C7 C3 C4 C12 -178.72(19) . . . . ?
C13 C14 C15 C16 2.8(3) . . . . ?
C16 C17 C18 C13 1.5(3) . . . . ?
C14 C13 C18 C17 -1.0(3) . . . . ?
C10 C13 C18 C17 -178.12(15) . . . . ?
C14 C15 C16 C17 -2.2(3) . . . . ?
C14 C15 C16 Cl19 176.88(14) . . . . ?
C18 C17 C16 C15 0.1(3) . . . . ?
C18 C17 C16 Cl19 -178.99(13) . . . . ?

_refine_diff_density_max         0.241
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.062

