# Supplementary Information (SI) for Materials 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_ICZTCNQ-200K
_database_code_depnum_ccdc_archive 'CCDC 2421738'
loop_
_audit_author_name
_audit_author_address
'Ruben A Toscano'
;Instituto de Quimica Universidad Nacional Autonoma de Mexico
Mexico
;
_audit_update_record             
;
2025-02-05 deposited with the CCDC.	2025-05-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H15 N5'
_chemical_formula_weight         445.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0034 0.0017
'XDISP Program in WinGX S.Brennan & P.L.Cowan Rev.Sci.Instrum.63,850 1992'
H H 0.0000 0.0000
'XDISP Program in WinGX S.Brennan & P.L.Cowan Rev.Sci.Instrum.63,850 1992'
N N 0.0065 0.0035
'XDISP Program in WinGX S.Brennan & P.L.Cowan Rev.Sci.Instrum.63,850 1992'

_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                   9.2049(10)
_cell_length_b                   7.1344(8)
_cell_length_c                   33.241(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.141(4)
_cell_angle_gamma                90
_cell_volume                     2170.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9865
_cell_measurement_theta_min      2.9953
_cell_measurement_theta_max      27.8086

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_F_000             920
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   0.958
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.941
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_process_details   'SADABS 2016/2 Bruker AXS Madison WI USA'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.7288
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source beamline 12.2.1'
_diffrn_measurement_device_type  'Bruker D8 with PHOTONII detector'
_diffrn_measurement_method       'ω/θ shutterless scans'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            56733
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_av_R_equivalents  0.0662
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         2.302
_diffrn_reflns_theta_max         27.929
_diffrn_reflns_theta_full        25.930
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4780
_reflns_number_gt                3966
_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       'Bruker APEX 3'
_computing_cell_refinement       'Bruker SAINT v8.40a'
_computing_data_reduction        'Bruker SAINT v8.40a'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL & local programs'
_refine_special_details          
;
 All non-hydrogen atoms were refined anisotropically. Hydrogen atoms
 were placed gemoetrically then constrained and  refined with a
 riding model. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0434P)²+0.6227P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'Dual space'
_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         4780
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.1021
_refine_ls_wR_factor_gt          0.0951
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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
N1 N 0.31822(10) 0.47553(14) 0.62442(3) 0.0248(2) Uani 1 1 d . . . . .
C1 C 0.28625(13) 0.41133(17) 0.66265(3) 0.0257(3) Uani 1 1 d . . . . .
C2 C 0.15328(14) 0.3873(2) 0.67773(4) 0.0354(3) Uani 1 1 d . . . . .
H2A H 0.064295 0.421318 0.662318 0.043 Uiso 1 1 calc R U . . .
C3 C 0.15463(16) 0.3115(2) 0.71622(4) 0.0446(4) Uani 1 1 d . . . . .
H3A H 0.064629 0.290876 0.727086 0.054 Uiso 1 1 calc R U . . .
C4 C 0.28490(17) 0.2650(2) 0.73927(4) 0.0440(4) Uani 1 1 d . . . . .
H4A H 0.282298 0.216141 0.765766 0.053 Uiso 1 1 calc R U . . .
C5 C 0.41816(15) 0.28877(19) 0.72419(4) 0.0347(3) Uani 1 1 d . . . . .
H5A H 0.506434 0.256480 0.740143 0.042 Uiso 1 1 calc R U . . .
C6 C 0.42119(13) 0.36063(17) 0.68534(3) 0.0261(3) Uani 1 1 d . . . . .
C7 C 0.53841(12) 0.39189(16) 0.65928(3) 0.0248(2) Uani 1 1 d . . . . .
C8 C 0.68889(13) 0.37180(17) 0.65782(4) 0.0280(3) Uani 1 1 d . . . . .
H8A H 0.750099 0.325610 0.680478 0.034 Uiso 1 1 calc R U . . .
C9 C 0.74714(13) 0.42187(18) 0.62187(4) 0.0294(3) Uani 1 1 d . . . . .
H9A H 0.849257 0.405993 0.621057 0.035 Uiso 1 1 calc R U . . .
C10 C 0.66580(13) 0.49354(17) 0.58710(4) 0.0273(3) Uani 1 1 d . . . . .
H10A H 0.711836 0.527739 0.563926 0.033 Uiso 1 1 calc R U . . .
C11 C 0.51474(12) 0.51297(16) 0.58769(3) 0.0239(2) Uani 1 1 d . . . . .
C12 C 0.46530(12) 0.45953(16) 0.62381(3) 0.0242(2) Uani 1 1 d . . . . .
C13 C 0.38132(12) 0.57231(16) 0.56281(3) 0.0248(2) Uani 1 1 d . . . . .
C14 C 0.35355(14) 0.64297(17) 0.52373(4) 0.0288(3) Uani 1 1 d . . . . .
H14A H 0.431086 0.660289 0.507397 0.035 Uiso 1 1 calc R U . . .
C15 C 0.21116(14) 0.68779(18) 0.50895(4) 0.0330(3) Uani 1 1 d . . . . .
H15A H 0.191333 0.735212 0.482216 0.040 Uiso 1 1 calc R U . . .
C16 C 0.09672(14) 0.66418(18) 0.53278(4) 0.0339(3) Uani 1 1 d . . . . .
H16A H 0.000397 0.697023 0.521942 0.041 Uiso 1 1 calc R U . . .
C17 C 0.11958(13) 0.59403(18) 0.57190(4) 0.0303(3) Uani 1 1 d . . . . .
H17A H 0.041068 0.578549 0.587969 0.036 Uiso 1 1 calc R U . . .
C18 C 0.26168(13) 0.54750(16) 0.58655(3) 0.0248(2) Uani 1 1 d . . . . .
C19 C 0.36547(12) 1.02004(16) 0.59243(3) 0.0246(2) Uani 1 1 d . . . . .
C20 C 0.51399(13) 1.01936(17) 0.58192(4) 0.0261(3) Uani 1 1 d . . . . .
H20A H 0.532871 1.059844 0.555749 0.031 Uiso 1 1 calc R U . . .
C21 C 0.62570(13) 0.96259(17) 0.60844(4) 0.0271(3) Uani 1 1 d . . . . .
H21A H 0.722470 0.965819 0.600991 0.032 Uiso 1 1 calc R U . . .
C22 C 0.60008(12) 0.89647(17) 0.64829(3) 0.0252(2) Uani 1 1 d . . . . .
C23 C 0.45143(12) 0.89275(17) 0.65841(4) 0.0267(3) Uani 1 1 d . . . . .
H23A H 0.431947 0.846555 0.684098 0.032 Uiso 1 1 calc R U . . .
C24 C 0.33962(13) 0.95367(17) 0.63208(4) 0.0262(3) Uani 1 1 d . . . . .
H24A H 0.243043 0.952866 0.639692 0.031 Uiso 1 1 calc R U . . .
C25 C 0.25224(13) 1.08193(16) 0.56512(4) 0.0267(3) Uani 1 1 d . . . . .
C26 C 0.27491(13) 1.13827(17) 0.52488(4) 0.0297(3) Uani 1 1 d . . . . .
N2 N 0.29188(13) 1.18028(18) 0.49239(4) 0.0418(3) Uani 1 1 d . . . . .
C27 C 0.10418(13) 1.09330(18) 0.57459(4) 0.0306(3) Uani 1 1 d . . . . .
N3 N -0.01535(12) 1.10699(19) 0.58114(4) 0.0440(3) Uani 1 1 d . . . . .
C28 C 0.71413(13) 0.83761(18) 0.67561(4) 0.0282(3) Uani 1 1 d . . . . .
C29 C 0.69225(13) 0.76358(19) 0.71459(4) 0.0311(3) Uani 1 1 d . . . . .
N4 N 0.67851(13) 0.7007(2) 0.74575(3) 0.0432(3) Uani 1 1 d . . . . .
C30 C 0.86358(13) 0.8422(2) 0.66699(4) 0.0340(3) Uani 1 1 d . . . . .
N5 N 0.98426(13) 0.8424(2) 0.66126(4) 0.0513(4) 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
N1 C12 1.3610(14) . ?
N1 C18 1.4069(15) . ?
N1 C1 1.4112(15) . ?
C1 C2 1.3819(17) . ?
C1 C6 1.4289(17) . ?
C2 C3 1.3879(19) . ?
C3 C4 1.392(2) . ?
C4 C5 1.3842(19) . ?
C5 C6 1.3925(17) . ?
C6 C7 1.4711(16) . ?
C7 C12 1.3805(16) . ?
C7 C8 1.3985(16) . ?
C8 C9 1.4072(17) . ?
C9 C10 1.4045(17) . ?
C10 C11 1.3996(16) . ?
C11 C12 1.3823(16) . ?
C11 C13 1.4677(16) . ?
C13 C14 1.3913(16) . ?
C13 C18 1.4327(17) . ?
C14 C15 1.3871(18) . ?
C15 C16 1.3943(19) . ?
C16 C17 1.3881(18) . ?
C17 C18 1.3863(16) . ?
C19 C25 1.3795(16) . ?
C19 C24 1.4439(17) . ?
C19 C20 1.4468(16) . ?
C20 C21 1.3434(17) . ?
C21 C22 1.4490(16) . ?
C22 C28 1.3782(16) . ?
C22 C23 1.4439(16) . ?
C23 C24 1.3497(17) . ?
C25 C26 1.4331(17) . ?
C25 C27 1.4335(17) . ?
C26 N2 1.1475(17) . ?
C27 N3 1.1484(16) . ?
C28 C29 1.4330(18) . ?
C28 C30 1.4353(17) . ?
C29 N4 1.1481(17) . ?
C30 N5 1.1470(17) . ?

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
C12 N1 C18 106.90(9) . . ?
C12 N1 C1 106.85(9) . . ?
C18 N1 C1 146.25(10) . . ?
C2 C1 N1 130.16(11) . . ?
C2 C1 C6 122.06(11) . . ?
N1 C1 C6 107.70(10) . . ?
C1 C2 C3 117.50(12) . . ?
C2 C3 C4 121.49(13) . . ?
C5 C4 C3 121.06(13) . . ?
C4 C5 C6 119.17(12) . . ?
C5 C6 C1 118.69(11) . . ?
C5 C6 C7 133.68(11) . . ?
C1 C6 C7 107.57(10) . . ?
C12 C7 C8 113.60(11) . . ?
C12 C7 C6 103.57(10) . . ?
C8 C7 C6 142.79(11) . . ?
C7 C8 C9 118.18(11) . . ?
C10 C9 C8 124.97(11) . . ?
C11 C10 C9 117.87(11) . . ?
C12 C11 C10 113.88(10) . . ?
C12 C11 C13 103.63(10) . . ?
C10 C11 C13 142.50(11) . . ?
N1 C12 C7 114.29(10) . . ?
N1 C12 C11 114.22(10) . . ?
C7 C12 C11 131.49(11) . . ?
C14 C13 C18 118.92(11) . . ?
C14 C13 C11 133.60(11) . . ?
C18 C13 C11 107.47(10) . . ?
C15 C14 C13 119.12(12) . . ?
C14 C15 C16 120.89(12) . . ?
C17 C16 C15 121.86(11) . . ?
C18 C17 C16 117.27(12) . . ?
C17 C18 N1 130.29(11) . . ?
C17 C18 C13 121.93(11) . . ?
N1 C18 C13 107.77(10) . . ?
C25 C19 C24 121.26(11) . . ?
C25 C19 C20 120.60(11) . . ?
C24 C19 C20 118.14(10) . . ?
C21 C20 C19 121.28(11) . . ?
C20 C21 C22 120.67(11) . . ?
C28 C22 C23 120.99(11) . . ?
C28 C22 C21 120.98(11) . . ?
C23 C22 C21 118.03(10) . . ?
C24 C23 C22 121.25(11) . . ?
C23 C24 C19 120.59(11) . . ?
C19 C25 C26 121.92(11) . . ?
C19 C25 C27 122.87(11) . . ?
C26 C25 C27 115.20(10) . . ?
N2 C26 C25 178.71(14) . . ?
N3 C27 C25 177.63(14) . . ?
C22 C28 C29 122.50(11) . . ?
C22 C28 C30 122.70(11) . . ?
C29 C28 C30 114.79(10) . . ?
N4 C29 C28 177.84(14) . . ?
N5 C30 C28 177.69(14) . . ?

_refine_diff_density_max         0.208
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_ICZ
_database_code_depnum_ccdc_archive 'CCDC 2421755'
loop_
_audit_author_name
_audit_author_address
'Ruben A Toscano'
;Instituto de Quimica Universidad Nacional Autonoma de Mexico
Mexico
;
_audit_update_record             
;
2025-02-05 deposited with the CCDC.	2025-05-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H11 N'
_chemical_formula_sum            'C18 H11 N'
_chemical_formula_weight         241.28

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

_cell_length_a                   26.734(2)
_cell_length_b                   5.1426(4)
_cell_length_c                   35.293(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4852.1(6)
_cell_formula_units_Z            16
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    8317
_cell_measurement_theta_min      3.54
_cell_measurement_theta_max      69.75

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_F_000             2016
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.417
_exptl_crystal_size_mid          0.064
_exptl_crystal_size_min          0.046
_exptl_absorpt_coefficient_mu    0.593
_shelx_estimated_absorpt_T_min   0.790
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6176
_exptl_absorpt_correction_T_max  0.7535
_exptl_absorpt_process_details   '(Sheldrick, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus X-ray source'
_diffrn_radiation_monochromator  'Helios multilayer mirror'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 83.333
_diffrn_reflns_number            36911
_diffrn_reflns_av_unetI/netI     0.0899
_diffrn_reflns_av_R_equivalents  0.0847
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         2.504
_diffrn_reflns_theta_max         70.048
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.778
_diffrn_reflns_point_group_measured_fraction_full 0.791
_reflns_number_total             7184
_reflns_number_gt                3965
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.540
_reflns_Friedel_fraction_max     0.556
_reflns_Friedel_fraction_full    0.579

_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 v2019.1-0(Bruker, 2019)'
_computing_cell_refinement       'APEX3 v2019.1-0(Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2014)'
_computing_structure_solution    'SHELXS-2012 (Bruker, 2013)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXLe (Hübschle et al, 2011)'
_computing_publication_material  'CIFTAB V 2013/2 (Sheldrick, 2013)'
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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_abs_structure_details 
;
 Flack x determined using 1177 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.6(10)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         7184
_refine_ls_number_parameters     685
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1985
_refine_ls_R_factor_gt           0.1539
_refine_ls_wR_factor_ref         0.3855
_refine_ls_wR_factor_gt          0.3345
_refine_ls_goodness_of_fit_ref   1.276
_refine_ls_restrained_S_all      1.276
_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
C1 C 0.5351(7) 0.898(3) 0.3998(5) 0.083(5) Uani 1 1 d . . . . .
H1 H 0.506136 0.976351 0.408909 0.099 Uiso 1 1 calc R U . . .
C2 C 0.5577(6) 0.695(3) 0.4194(4) 0.077(4) Uani 1 1 d . . . . .
H2 H 0.542872 0.644828 0.442061 0.092 Uiso 1 1 calc R U . . .
C3 C 0.6017(7) 0.556(3) 0.4079(5) 0.077(5) Uani 1 1 d . . . . .
H3 H 0.615534 0.421765 0.422179 0.093 Uiso 1 1 calc R U . . .
C4 C 0.6985(6) 0.379(3) 0.3450(5) 0.076(4) Uani 1 1 d . . . . .
H4 H 0.702703 0.264810 0.365213 0.091 Uiso 1 1 calc R U . . .
C5 C 0.7286(5) 0.363(3) 0.3130(6) 0.079(5) Uani 1 1 d . . . . .
H5 H 0.752599 0.232232 0.312123 0.094 Uiso 1 1 calc R U . . .
C6 C 0.7249(5) 0.528(3) 0.2826(5) 0.066(4) Uani 1 1 d . . . . .
H6 H 0.745928 0.509566 0.261805 0.079 Uiso 1 1 calc R U . . .
C7 C 0.6886(5) 0.727(3) 0.2836(5) 0.065(4) Uani 1 1 d . . . . .
H7 H 0.685373 0.843579 0.263612 0.078 Uiso 1 1 calc R U . . .
N8 N 0.6183(4) 0.920(2) 0.3215(3) 0.063(3) Uani 1 1 d . . . . .
C9 C 0.5915(4) 1.251(2) 0.2751(4) 0.059(3) Uani 1 1 d . . . . .
H9 H 0.617717 1.213645 0.258641 0.071 Uiso 1 1 calc R U . . .
C10 C 0.5584(5) 1.452(3) 0.2653(4) 0.066(4) Uani 1 1 d . . . . .
H10 H 0.559746 1.545535 0.242747 0.079 Uiso 1 1 calc R U . . .
C11 C 0.5203(5) 1.497(2) 0.2965(4) 0.050(3) Uani 1 1 d . . . . .
H11 H 0.499036 1.638848 0.293868 0.061 Uiso 1 1 calc R U . . .
C12 C 0.5149(5) 1.355(2) 0.3260(5) 0.066(4) Uani 1 1 d . . . . .
H12 H 0.488294 1.385646 0.342356 0.079 Uiso 1 1 calc R U . . .
C13 C 0.6225(5) 0.640(2) 0.3728(4) 0.058(3) Uani 1 1 d . . . . .
C14 C 0.6623(4) 0.568(3) 0.3459(4) 0.055(3) Uani 1 1 d . . . . .
C15 C 0.6582(4) 0.744(2) 0.3149(4) 0.055(3) Uani 1 1 d . . . . .
C16 C 0.5871(4) 1.111(2) 0.3068(4) 0.049(3) Uani 1 1 d . . . . .
C17 C 0.5483(4) 1.159(2) 0.3336(4) 0.053(3) Uani 1 1 d . . . . .
C18 C 0.5576(5) 0.982(3) 0.3654(5) 0.061(4) Uani 1 1 d . . . . .
C19 C 0.5981(5) 0.845(2) 0.3563(4) 0.057(3) Uani 1 1 d . . . . .
C21 C 0.3510(5) 0.330(3) 0.4669(4) 0.069(4) Uani 1 1 d . . . . .
H21 H 0.342619 0.227280 0.487556 0.083 Uiso 1 1 calc R U . . .
C22 C 0.3960(5) 0.302(3) 0.4484(4) 0.069(4) Uani 1 1 d . . . . .
H22 H 0.417237 0.172060 0.457042 0.083 Uiso 1 1 calc R U . . .
C23 C 0.4135(6) 0.461(3) 0.4161(5) 0.067(4) Uani 1 1 d . . . . .
H23 H 0.444882 0.437985 0.405209 0.081 Uiso 1 1 calc R U . . .
C24 C 0.4053(5) 0.950(3) 0.3447(5) 0.066(4) Uani 1 1 d . . . . .
H24 H 0.438205 0.893820 0.341949 0.079 Uiso 1 1 calc R U . . .
C25 C 0.3884(6) 1.121(4) 0.3217(5) 0.083(5) Uani 1 1 d . . . . .
H25 H 0.407479 1.165005 0.300644 0.100 Uiso 1 1 calc R U . . .
C26 C 0.3433(6) 1.240(3) 0.3268(5) 0.084(5) Uani 1 1 d . . . . .
H26 H 0.333833 1.373872 0.310561 0.100 Uiso 1 1 calc R U . . .
C27 C 0.3120(5) 1.168(3) 0.3554(4) 0.065(4) Uani 1 1 d . . . . .
H27 H 0.280534 1.243214 0.358096 0.078 Uiso 1 1 calc R U . . .
N28 N 0.3049(4) 0.852(2) 0.4108(3) 0.057(3) Uani 1 1 d . . . . .
C29 C 0.2217(5) 1.007(3) 0.4347(5) 0.062(4) Uani 1 1 d . . . . .
H29 H 0.218524 1.136833 0.416501 0.074 Uiso 1 1 calc R U . . .
C30 C 0.1851(7) 0.973(3) 0.4618(6) 0.079(5) Uani 1 1 d . . . . .
H30 H 0.156884 1.079450 0.462215 0.095 Uiso 1 1 calc R U . . .
C31 C 0.1918(6) 0.765(3) 0.4900(5) 0.080(5) Uani 1 1 d . . . . .
H31 H 0.167478 0.737738 0.508473 0.096 Uiso 1 1 calc R U . . .
C32 C 0.2328(5) 0.614(3) 0.4893(4) 0.071(4) Uani 1 1 d . . . . .
H32 H 0.236662 0.484191 0.507438 0.085 Uiso 1 1 calc R U . . .
C33 C 0.3806(5) 0.643(3) 0.4036(4) 0.059(3) Uani 1 1 d . . . . .
C34 C 0.3754(5) 0.842(2) 0.3745(4) 0.057(3) Uani 1 1 d . . . . .
C35 C 0.3290(5) 0.972(3) 0.3812(4) 0.057(3) Uani 1 1 d . . . . .
C36 C 0.2623(5) 0.850(2) 0.4347(4) 0.059(3) Uani 1 1 d . . . . .
C37 C 0.2694(5) 0.647(2) 0.4618(4) 0.061(3) Uani 1 1 d . . . . .
C38 C 0.3193(5) 0.5148(17) 0.4535(4) 0.046(3) Uani 1 1 d . . . . .
C39 C 0.3360(5) 0.662(2) 0.4233(4) 0.057(3) Uani 1 1 d . . . . .
C41 C 0.3329(5) -0.032(3) 0.5783(5) 0.061(4) Uani 1 1 d . . . . .
H41 H 0.300887 -0.049978 0.588377 0.073 Uiso 1 1 calc R U . . .
C42 C 0.3483(6) -0.193(3) 0.5487(5) 0.076(4) Uani 1 1 d . . . . .
H42 H 0.327058 -0.326218 0.541061 0.092 Uiso 1 1 calc R U . . .
C43 C 0.3938(5) -0.165(3) 0.5298(4) 0.065(4) Uani 1 1 d . . . . .
H43 H 0.402343 -0.274191 0.509844 0.078 Uiso 1 1 calc R U . . .
C44 C 0.5114(5) 0.108(3) 0.5085(4) 0.069(4) Uani 1 1 d . . . . .
H44 H 0.508314 -0.026154 0.490886 0.083 Uiso 1 1 calc R U . . .
C45 C 0.5530(5) 0.269(3) 0.5083(5) 0.078(5) Uani 1 1 d . . . . .
H45 H 0.577905 0.236173 0.490515 0.093 Uiso 1 1 calc R U . . .
C46 C 0.5594(5) 0.474(3) 0.5329(5) 0.068(4) Uani 1 1 d . . . . .
H46 H 0.586373 0.587262 0.530478 0.082 Uiso 1 1 calc R U . . .
C47 C 0.5233(5) 0.505(2) 0.5619(4) 0.056(4) Uani 1 1 d . . . . .
H47 H 0.528340 0.627444 0.580997 0.067 Uiso 1 1 calc R U . . .
N48 N 0.4394(4) 0.3547(19) 0.5863(3) 0.055(3) Uani 1 1 d . . . . .
C49 C 0.4319(5) 0.670(3) 0.6406(4) 0.065(4) Uani 1 1 d . . . . .
H49 H 0.462567 0.751276 0.636860 0.078 Uiso 1 1 calc R U . . .
C50 C 0.4001(6) 0.746(3) 0.6693(4) 0.071(4) Uani 1 1 d . . . . .
H50 H 0.409626 0.880310 0.685432 0.085 Uiso 1 1 calc R U . . .
C51 C 0.3539(6) 0.626(3) 0.6746(5) 0.082(5) Uani 1 1 d . . . . .
H51 H 0.332563 0.690427 0.693168 0.098 Uiso 1 1 calc R U . . .
C52 C 0.3381(6) 0.409(3) 0.6530(5) 0.082(5) Uani 1 1 d . . . . .
H52 H 0.309221 0.316317 0.658635 0.098 Uiso 1 1 calc R U . . .
C53 C 0.4264(5) 0.032(3) 0.5418(4) 0.061(4) Uani 1 1 d . . . . .
C54 C 0.4744(5) 0.150(2) 0.5355(4) 0.059(3) Uani 1 1 d . . . . .
C55 C 0.4816(5) 0.357(3) 0.5619(4) 0.059(3) Uani 1 1 d . . . . .
C56 C 0.4171(5) 0.481(2) 0.6189(4) 0.045(3) Uani 1 1 d . . . . .
C57 C 0.3690(5) 0.345(3) 0.6227(4) 0.056(3) Uani 1 1 d . . . . .
C58 C 0.3641(5) 0.149(2) 0.5924(4) 0.057(3) Uani 1 1 d . . . . .
C59 C 0.4080(5) 0.164(2) 0.5730(4) 0.056(3) Uani 1 1 d . . . . .
C61 C 0.6441(7) 0.943(3) 0.5902(5) 0.075(4) Uani 1 1 d . . . . .
H61 H 0.631564 1.083866 0.576607 0.090 Uiso 1 1 calc R U . . .
C62 C 0.6847(6) 0.809(3) 0.5773(5) 0.083(4) Uani 1 1 d . . . . .
H62 H 0.698203 0.856441 0.554031 0.100 Uiso 1 1 calc R U . . .
C63 C 0.7077(6) 0.601(3) 0.5971(4) 0.076(4) Uani 1 1 d . . . . .
H63 H 0.735848 0.520627 0.586911 0.091 Uiso 1 1 calc R U . . .
C64 C 0.7286(5) 0.152(2) 0.6714(5) 0.067(4) Uani 1 1 d . . . . .
H64 H 0.751824 0.102170 0.653172 0.080 Uiso 1 1 calc R U . . .
C65 C 0.7265(7) 0.018(2) 0.7095(5) 0.063(4) Uani 1 1 d . . . . .
H65 H 0.750883 -0.099805 0.717180 0.075 Uiso 1 1 calc R U . . .
C66 C 0.6900(6) 0.074(3) 0.7300(5) 0.082(5) Uani 1 1 d . . . . .
H66 H 0.686278 -0.028424 0.751543 0.098 Uiso 1 1 calc R U . . .
C67 C 0.6531(5) 0.273(3) 0.7255(5) 0.068(4) Uani 1 1 d . . . . .
H67 H 0.629501 0.313618 0.743914 0.081 Uiso 1 1 calc R U . . .
N68 N 0.6266(4) 0.6021(17) 0.6766(3) 0.055(3) Uani 1 1 d . . . . .
C69 C 0.5552(5) 0.793(3) 0.7142(4) 0.062(4) Uani 1 1 d . . . . .
H69 H 0.556907 0.677480 0.734417 0.074 Uiso 1 1 calc R U . . .
C70 C 0.5213(6) 0.988(2) 0.7139(5) 0.064(4) Uani 1 1 d . . . . .
H70 H 0.501260 1.012477 0.735189 0.077 Uiso 1 1 calc R U . . .
C71 C 0.5151(6) 1.153(3) 0.6833(6) 0.080(5) Uani 1 1 d . . . . .
H71 H 0.489903 1.277235 0.683656 0.096 Uiso 1 1 calc R U . . .
C72 C 0.5464(5) 1.133(3) 0.6521(5) 0.071(4) Uani 1 1 d . . . . .
H72 H 0.543809 1.250762 0.632188 0.085 Uiso 1 1 calc R U . . .
C73 C 0.6887(5) 0.5156(18) 0.6313(4) 0.048(3) Uani 1 1 d . . . . .
C74 C 0.6953(5) 0.347(2) 0.6646(4) 0.057(3) Uani 1 1 d . . . . .
C75 C 0.6562(6) 0.401(2) 0.6901(4) 0.065(4) Uani 1 1 d . . . . .
C76 C 0.5872(4) 0.770(2) 0.6837(4) 0.058(3) Uani 1 1 d . . . . .
C77 C 0.5809(6) 0.940(3) 0.6513(4) 0.064(4) Uani 1 1 d . . . . .
C78 C 0.6217(6) 0.865(2) 0.6245(4) 0.063(4) Uani 1 1 d . . . . .
C79 C 0.6458(5) 0.664(2) 0.6414(4) 0.058(3) 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
C1 C2 1.39(2) . ?
C1 C18 1.42(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.44(2) . ?
C2 H2 0.9300 . ?
C3 C13 1.42(2) . ?
C3 H3 0.9300 . ?
C4 C14 1.370(19) . ?
C4 C5 1.39(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.37(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.410(18) . ?
C6 H6 0.9300 . ?
C7 C15 1.375(18) . ?
C7 H7 0.9300 . ?
N8 C16 1.388(16) . ?
N8 C19 1.396(17) . ?
N8 C15 1.417(16) . ?
C9 C16 1.339(18) . ?
C9 C10 1.402(18) . ?
C9 H9 0.9300 . ?
C10 C11 1.518(18) . ?
C10 H10 0.9300 . ?
C11 C12 1.279(19) . ?
C11 H11 0.9300 . ?
C12 C17 1.374(16) . ?
C12 H12 0.9300 . ?
C13 C19 1.370(17) . ?
C13 C14 1.476(19) . ?
C14 C15 1.426(19) . ?
C16 C17 1.427(16) . ?
C17 C18 1.47(2) . ?
C18 C19 1.331(18) . ?
C21 C38 1.356(17) . ?
C21 C22 1.38(2) . ?
C21 H21 0.9300 . ?
C22 C23 1.48(2) . ?
C22 H22 0.9300 . ?
C23 C33 1.360(19) . ?
C23 H23 0.9300 . ?
C24 C25 1.28(2) . ?
C24 C34 1.435(19) . ?
C24 H24 0.9300 . ?
C25 C26 1.36(2) . ?
C25 H25 0.9300 . ?
C26 C27 1.36(2) . ?
C26 H26 0.9300 . ?
C27 C35 1.432(19) . ?
C27 H27 0.9300 . ?
N28 C39 1.356(14) . ?
N28 C35 1.376(17) . ?
N28 C36 1.416(16) . ?
C29 C36 1.353(18) . ?
C29 C30 1.38(2) . ?
C29 H29 0.9300 . ?
C30 C31 1.48(2) . ?
C30 H30 0.9300 . ?
C31 C32 1.34(2) . ?
C31 H31 0.9300 . ?
C32 C37 1.387(19) . ?
C32 H32 0.9300 . ?
C33 C39 1.384(18) . ?
C33 C34 1.453(19) . ?
C34 C35 1.428(18) . ?
C36 C37 1.429(19) . ?
C37 C38 1.525(19) . ?
C38 C39 1.382(19) . ?
C41 C58 1.345(17) . ?
C41 C42 1.40(2) . ?
C41 H41 0.9300 . ?
C42 C43 1.39(2) . ?
C42 H42 0.9300 . ?
C43 C53 1.400(18) . ?
C43 H43 0.9300 . ?
C44 C45 1.39(2) . ?
C44 C54 1.393(19) . ?
C44 H44 0.9300 . ?
C45 C46 1.38(2) . ?
C45 H45 0.9300 . ?
C46 C47 1.42(2) . ?
C46 H46 0.9300 . ?
C47 C55 1.351(17) . ?
C47 H47 0.9300 . ?
N48 C59 1.374(15) . ?
N48 C55 1.419(16) . ?
N48 C56 1.451(17) . ?
C49 C56 1.299(18) . ?
C49 C50 1.38(2) . ?
C49 H49 0.9300 . ?
C50 C51 1.39(2) . ?
C50 H50 0.9300 . ?
C51 C52 1.41(2) . ?
C51 H51 0.9300 . ?
C52 C57 1.39(2) . ?
C52 H52 0.9300 . ?
C53 C59 1.385(19) . ?
C53 C54 1.437(19) . ?
C54 C55 1.426(19) . ?
C56 C57 1.469(18) . ?
C57 C58 1.474(18) . ?
C58 C59 1.360(17) . ?
C61 C62 1.37(2) . ?
C61 C78 1.41(2) . ?
C61 H61 0.9300 . ?
C62 C63 1.42(2) . ?
C62 H62 0.9300 . ?
C63 C73 1.382(19) . ?
C63 H63 0.9300 . ?
C64 C74 1.362(16) . ?
C64 C65 1.51(2) . ?
C64 H64 0.9300 . ?
C65 C66 1.25(2) . ?
C65 H65 0.9300 . ?
C66 C67 1.43(2) . ?
C66 H66 0.9300 . ?
C67 C75 1.42(2) . ?
C67 H67 0.9300 . ?
N68 C79 1.379(17) . ?
N68 C75 1.385(17) . ?
N68 C76 1.385(15) . ?
C69 C70 1.352(18) . ?
C69 C76 1.380(18) . ?
C69 H69 0.9300 . ?
C70 C71 1.38(2) . ?
C70 H70 0.9300 . ?
C71 C72 1.39(2) . ?
C71 H71 0.9300 . ?
C72 C77 1.35(2) . ?
C72 H72 0.9300 . ?
C73 C79 1.421(18) . ?
C73 C74 1.472(18) . ?
C74 C75 1.408(19) . ?
C76 C77 1.45(2) . ?
C77 C78 1.50(2) . ?
C78 C79 1.359(17) . ?

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
C2 C1 C18 117.9(15) . . ?
C2 C1 H1 121.0 . . ?
C18 C1 H1 121.0 . . ?
C1 C2 C3 126.2(15) . . ?
C1 C2 H2 116.9 . . ?
C3 C2 H2 116.9 . . ?
C13 C3 C2 114.4(14) . . ?
C13 C3 H3 122.8 . . ?
C2 C3 H3 122.8 . . ?
C14 C4 C5 118.0(14) . . ?
C14 C4 H4 121.0 . . ?
C5 C4 H4 121.0 . . ?
C6 C5 C4 123.9(14) . . ?
C6 C5 H5 118.1 . . ?
C4 C5 H5 118.1 . . ?
C5 C6 C7 118.6(16) . . ?
C5 C6 H6 120.7 . . ?
C7 C6 H6 120.7 . . ?
C15 C7 C6 118.3(14) . . ?
C15 C7 H7 120.9 . . ?
C6 C7 H7 120.9 . . ?
C16 N8 C19 107.0(10) . . ?
C16 N8 C15 147.4(12) . . ?
C19 N8 C15 105.0(11) . . ?
C16 C9 C10 123.2(13) . . ?
C16 C9 H9 118.4 . . ?
C10 C9 H9 118.4 . . ?
C9 C10 C11 110.9(13) . . ?
C9 C10 H10 124.6 . . ?
C11 C10 H10 124.6 . . ?
C12 C11 C10 125.5(12) . . ?
C12 C11 H11 117.3 . . ?
C10 C11 H11 117.3 . . ?
C11 C12 C17 120.4(14) . . ?
C11 C12 H12 119.8 . . ?
C17 C12 H12 119.8 . . ?
C19 C13 C3 114.8(13) . . ?
C19 C13 C14 105.2(12) . . ?
C3 C13 C14 139.9(13) . . ?
C4 C14 C15 119.3(14) . . ?
C4 C14 C13 134.6(14) . . ?
C15 C14 C13 106.1(11) . . ?
C7 C15 N8 128.2(13) . . ?
C7 C15 C14 121.9(12) . . ?
N8 C15 C14 109.8(12) . . ?
C9 C16 N8 129.9(11) . . ?
C9 C16 C17 121.7(12) . . ?
N8 C16 C17 108.2(11) . . ?
C12 C17 C16 118.0(13) . . ?
C12 C17 C18 135.9(13) . . ?
C16 C17 C18 106.0(10) . . ?
C19 C18 C1 113.0(14) . . ?
C19 C18 C17 106.3(13) . . ?
C1 C18 C17 140.3(13) . . ?
C18 C19 C13 133.6(14) . . ?
C18 C19 N8 112.4(12) . . ?
C13 C19 N8 113.8(12) . . ?
C38 C21 C22 117.1(14) . . ?
C38 C21 H21 121.4 . . ?
C22 C21 H21 121.4 . . ?
C21 C22 C23 125.8(13) . . ?
C21 C22 H22 117.1 . . ?
C23 C22 H22 117.1 . . ?
C33 C23 C22 115.2(13) . . ?
C33 C23 H23 122.4 . . ?
C22 C23 H23 122.4 . . ?
C25 C24 C34 122.3(14) . . ?
C25 C24 H24 118.9 . . ?
C34 C24 H24 118.9 . . ?
C24 C25 C26 122.6(16) . . ?
C24 C25 H25 118.7 . . ?
C26 C25 H25 118.7 . . ?
C27 C26 C25 121.1(15) . . ?
C27 C26 H26 119.4 . . ?
C25 C26 H26 119.4 . . ?
C26 C27 C35 117.8(14) . . ?
C26 C27 H27 121.1 . . ?
C35 C27 H27 121.1 . . ?
C39 N28 C35 106.4(11) . . ?
C39 N28 C36 107.2(11) . . ?
C35 N28 C36 146.3(11) . . ?
C36 C29 C30 119.7(15) . . ?
C36 C29 H29 120.2 . . ?
C30 C29 H29 120.2 . . ?
C29 C30 C31 118.2(14) . . ?
C29 C30 H30 120.9 . . ?
C31 C30 H30 120.9 . . ?
C32 C31 C30 120.4(15) . . ?
C32 C31 H31 119.8 . . ?
C30 C31 H31 119.8 . . ?
C31 C32 C37 121.2(16) . . ?
C31 C32 H32 119.4 . . ?
C37 C32 H32 119.4 . . ?
C23 C33 C39 116.2(14) . . ?
C23 C33 C34 140.9(13) . . ?
C39 C33 C34 102.9(11) . . ?
C35 C34 C24 115.0(12) . . ?
C35 C34 C33 107.2(11) . . ?
C24 C34 C33 137.4(12) . . ?
N28 C35 C34 108.7(12) . . ?
N28 C35 C27 130.5(13) . . ?
C34 C35 C27 120.1(13) . . ?
C29 C36 N28 129.8(13) . . ?
C29 C36 C37 122.8(14) . . ?
N28 C36 C37 107.3(11) . . ?
C32 C37 C36 117.7(13) . . ?
C32 C37 C38 134.1(14) . . ?
C36 C37 C38 108.2(12) . . ?
C21 C38 C39 116.7(13) . . ?
C21 C38 C37 142.3(14) . . ?
C39 C38 C37 100.8(10) . . ?
N28 C39 C38 116.5(11) . . ?
N28 C39 C33 114.5(13) . . ?
C38 C39 C33 129.0(12) . . ?
C58 C41 C42 120.2(14) . . ?
C58 C41 H41 119.9 . . ?
C42 C41 H41 119.9 . . ?
C43 C42 C41 123.7(13) . . ?
C43 C42 H42 118.2 . . ?
C41 C42 H42 118.2 . . ?
C42 C43 C53 118.3(13) . . ?
C42 C43 H43 120.9 . . ?
C53 C43 H43 120.9 . . ?
C45 C44 C54 118.7(15) . . ?
C45 C44 H44 120.7 . . ?
C54 C44 H44 120.7 . . ?
C46 C45 C44 123.8(15) . . ?
C46 C45 H45 118.1 . . ?
C44 C45 H45 118.1 . . ?
C45 C46 C47 117.2(14) . . ?
C45 C46 H46 121.4 . . ?
C47 C46 H46 121.4 . . ?
C55 C47 C46 119.8(14) . . ?
C55 C47 H47 120.1 . . ?
C46 C47 H47 120.1 . . ?
C59 N48 C55 106.5(11) . . ?
C59 N48 C56 109.8(10) . . ?
C55 N48 C56 143.6(10) . . ?
C56 C49 C50 117.2(14) . . ?
C56 C49 H49 121.4 . . ?
C50 C49 H49 121.4 . . ?
C49 C50 C51 121.2(14) . . ?
C49 C50 H50 119.4 . . ?
C51 C50 H50 119.4 . . ?
C50 C51 C52 122.8(15) . . ?
C50 C51 H51 118.6 . . ?
C52 C51 H51 118.6 . . ?
C57 C52 C51 115.2(15) . . ?
C57 C52 H52 122.4 . . ?
C51 C52 H52 122.4 . . ?
C59 C53 C43 111.9(12) . . ?
C59 C53 C54 103.5(12) . . ?
C43 C53 C54 144.6(14) . . ?
C44 C54 C55 117.9(13) . . ?
C44 C54 C53 132.4(13) . . ?
C55 C54 C53 109.6(12) . . ?
C47 C55 N48 131.3(13) . . ?
C47 C55 C54 122.2(13) . . ?
N48 C55 C54 106.4(11) . . ?
C49 C56 N48 132.6(12) . . ?
C49 C56 C57 124.8(13) . . ?
N48 C56 C57 102.6(10) . . ?
C52 C57 C56 118.3(13) . . ?
C52 C57 C58 131.8(13) . . ?
C56 C57 C58 109.8(11) . . ?
C41 C58 C59 112.8(13) . . ?
C41 C58 C57 142.7(14) . . ?
C59 C58 C57 104.5(11) . . ?
C58 C59 N48 113.3(11) . . ?
C58 C59 C53 132.8(12) . . ?
N48 C59 C53 113.8(12) . . ?
C62 C61 C78 118.6(14) . . ?
C62 C61 H61 120.7 . . ?
C78 C61 H61 120.7 . . ?
C61 C62 C63 124.3(15) . . ?
C61 C62 H62 117.9 . . ?
C63 C62 H62 117.9 . . ?
C73 C63 C62 120.7(14) . . ?
C73 C63 H63 119.7 . . ?
C62 C63 H63 119.7 . . ?
C74 C64 C65 117.9(14) . . ?
C74 C64 H64 121.1 . . ?
C65 C64 H64 121.1 . . ?
C66 C65 C64 116.0(13) . . ?
C66 C65 H65 122.0 . . ?
C64 C65 H65 122.0 . . ?
C65 C66 C67 129.8(15) . . ?
C65 C66 H66 115.1 . . ?
C67 C66 H66 115.1 . . ?
C75 C67 C66 113.1(15) . . ?
C75 C67 H67 123.4 . . ?
C66 C67 H67 123.4 . . ?
C79 N68 C75 105.6(11) . . ?
C79 N68 C76 107.6(10) . . ?
C75 N68 C76 146.8(12) . . ?
C70 C69 C76 118.3(14) . . ?
C70 C69 H69 120.8 . . ?
C76 C69 H69 120.8 . . ?
C69 C70 C71 122.6(15) . . ?
C69 C70 H70 118.7 . . ?
C71 C70 H70 118.7 . . ?
C70 C71 C72 120.3(15) . . ?
C70 C71 H71 119.8 . . ?
C72 C71 H71 119.8 . . ?
C77 C72 C71 118.7(15) . . ?
C77 C72 H72 120.6 . . ?
C71 C72 H72 120.6 . . ?
C63 C73 C79 110.3(12) . . ?
C63 C73 C74 147.2(13) . . ?
C79 C73 C74 102.2(11) . . ?
C64 C74 C75 121.3(13) . . ?
C64 C74 C73 130.8(14) . . ?
C75 C74 C73 107.6(11) . . ?
N68 C75 C74 110.6(11) . . ?
N68 C75 C67 128.2(13) . . ?
C74 C75 C67 121.0(13) . . ?
C69 C76 N68 131.8(13) . . ?
C69 C76 C77 119.4(12) . . ?
N68 C76 C77 108.8(12) . . ?
C72 C77 C76 120.3(15) . . ?
C72 C77 C78 134.4(15) . . ?
C76 C77 C78 104.9(12) . . ?
C79 C78 C61 113.3(14) . . ?
C79 C78 C77 105.3(13) . . ?
C61 C78 C77 141.2(13) . . ?
C78 C79 N68 113.3(13) . . ?
C78 C79 C73 132.8(14) . . ?
N68 C79 C73 113.8(11) . . ?

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
C18 C1 C2 C3 -1(2) . . . . ?
C1 C2 C3 C13 0(2) . . . . ?
C14 C4 C5 C6 1(2) . . . . ?
C4 C5 C6 C7 0(2) . . . . ?
C5 C6 C7 C15 -1(2) . . . . ?
C16 C9 C10 C11 3.6(18) . . . . ?
C9 C10 C11 C12 -6.9(19) . . . . ?
C10 C11 C12 C17 7(2) . . . . ?
C2 C3 C13 C19 2.0(18) . . . . ?
C2 C3 C13 C14 -173.8(16) . . . . ?
C5 C4 C14 C15 -2(2) . . . . ?
C5 C4 C14 C13 176.7(14) . . . . ?
C19 C13 C14 C4 -178.4(15) . . . . ?
C3 C13 C14 C4 -2(3) . . . . ?
C19 C13 C14 C15 0.6(14) . . . . ?
C3 C13 C14 C15 176.6(16) . . . . ?
C6 C7 C15 N8 -177.4(12) . . . . ?
C6 C7 C15 C14 -0.2(19) . . . . ?
C16 N8 C15 C7 9(3) . . . . ?
C19 N8 C15 C7 176.7(13) . . . . ?
C16 N8 C15 C14 -168.9(19) . . . . ?
C19 N8 C15 C14 -0.7(14) . . . . ?
C4 C14 C15 C7 1.7(19) . . . . ?
C13 C14 C15 C7 -177.5(11) . . . . ?
C4 C14 C15 N8 179.3(12) . . . . ?
C13 C14 C15 N8 0.1(14) . . . . ?
C10 C9 C16 N8 -175.3(13) . . . . ?
C10 C9 C16 C17 -0.7(19) . . . . ?
C19 N8 C16 C9 176.9(13) . . . . ?
C15 N8 C16 C9 -15(3) . . . . ?
C19 N8 C16 C17 1.7(14) . . . . ?
C15 N8 C16 C17 169.7(18) . . . . ?
C11 C12 C17 C16 -3.0(18) . . . . ?
C11 C12 C17 C18 171.9(14) . . . . ?
C9 C16 C17 C12 -0.1(17) . . . . ?
N8 C16 C17 C12 175.6(11) . . . . ?
C9 C16 C17 C18 -176.3(11) . . . . ?
N8 C16 C17 C18 -0.6(13) . . . . ?
C2 C1 C18 C19 1(2) . . . . ?
C2 C1 C18 C17 173.4(16) . . . . ?
C12 C17 C18 C19 -175.9(14) . . . . ?
C16 C17 C18 C19 -0.7(14) . . . . ?
C12 C17 C18 C1 11(3) . . . . ?
C16 C17 C18 C1 -173.4(18) . . . . ?
C1 C18 C19 C13 1(2) . . . . ?
C17 C18 C19 C13 -174.1(14) . . . . ?
C1 C18 C19 N8 176.7(12) . . . . ?
C17 C18 C19 N8 1.8(16) . . . . ?
C3 C13 C19 C18 -2(2) . . . . ?
C14 C13 C19 C18 174.7(16) . . . . ?
C3 C13 C19 N8 -178.3(12) . . . . ?
C14 C13 C19 N8 -1.2(15) . . . . ?
C16 N8 C19 C18 -2.2(16) . . . . ?
C15 N8 C19 C18 -175.6(12) . . . . ?
C16 N8 C19 C13 174.5(11) . . . . ?
C15 N8 C19 C13 1.2(15) . . . . ?
C38 C21 C22 C23 2(2) . . . . ?
C21 C22 C23 C33 -2(2) . . . . ?
C34 C24 C25 C26 10(3) . . . . ?
C24 C25 C26 C27 -5(3) . . . . ?
C25 C26 C27 C35 3(2) . . . . ?
C36 C29 C30 C31 0(2) . . . . ?
C29 C30 C31 C32 0(2) . . . . ?
C30 C31 C32 C37 -1(2) . . . . ?
C22 C23 C33 C39 2(2) . . . . ?
C22 C23 C33 C34 -178.2(16) . . . . ?
C25 C24 C34 C35 -11(2) . . . . ?
C25 C24 C34 C33 176.1(17) . . . . ?
C23 C33 C34 C35 -176.2(18) . . . . ?
C39 C33 C34 C35 3.5(14) . . . . ?
C23 C33 C34 C24 -3(3) . . . . ?
C39 C33 C34 C24 176.5(16) . . . . ?
C39 N28 C35 C34 2.9(15) . . . . ?
C36 N28 C35 C34 178.7(17) . . . . ?
C39 N28 C35 C27 173.6(14) . . . . ?
C36 N28 C35 C27 -11(3) . . . . ?
C24 C34 C35 N28 -178.8(12) . . . . ?
C33 C34 C35 N28 -4.1(15) . . . . ?
C24 C34 C35 C27 9.3(19) . . . . ?
C33 C34 C35 C27 -175.9(12) . . . . ?
C26 C27 C35 N28 -175.8(15) . . . . ?
C26 C27 C35 C34 -6(2) . . . . ?
C30 C29 C36 N28 -177.8(13) . . . . ?
C30 C29 C36 C37 0(2) . . . . ?
C39 N28 C36 C29 177.3(14) . . . . ?
C35 N28 C36 C29 1(3) . . . . ?
C39 N28 C36 C37 -0.6(13) . . . . ?
C35 N28 C36 C37 -176.4(19) . . . . ?
C31 C32 C37 C36 1(2) . . . . ?
C31 C32 C37 C38 179.1(14) . . . . ?
C29 C36 C37 C32 0(2) . . . . ?
N28 C36 C37 C32 177.9(11) . . . . ?
C29 C36 C37 C38 -179.0(12) . . . . ?
N28 C36 C37 C38 -0.9(14) . . . . ?
C22 C21 C38 C39 -1.9(18) . . . . ?
C22 C21 C38 C37 -174.6(15) . . . . ?
C32 C37 C38 C21 -3(3) . . . . ?
C36 C37 C38 C21 175.4(16) . . . . ?
C32 C37 C38 C39 -176.6(15) . . . . ?
C36 C37 C38 C39 2.0(13) . . . . ?
C35 N28 C39 C38 179.8(12) . . . . ?
C36 N28 C39 C38 2.2(14) . . . . ?
C35 N28 C39 C33 -0.6(15) . . . . ?
C36 N28 C39 C33 -178.2(11) . . . . ?
C21 C38 C39 N28 -178.1(11) . . . . ?
C37 C38 C39 N28 -2.6(14) . . . . ?
C21 C38 C39 C33 2(2) . . . . ?
C37 C38 C39 C33 177.8(13) . . . . ?
C23 C33 C39 N28 177.9(12) . . . . ?
C34 C33 C39 N28 -1.9(15) . . . . ?
C23 C33 C39 C38 -2(2) . . . . ?
C34 C33 C39 C38 177.7(12) . . . . ?
C58 C41 C42 C43 -6(2) . . . . ?
C41 C42 C43 C53 1(2) . . . . ?
C54 C44 C45 C46 -2(2) . . . . ?
C44 C45 C46 C47 6(2) . . . . ?
C45 C46 C47 C55 -8(2) . . . . ?
C56 C49 C50 C51 0(2) . . . . ?
C49 C50 C51 C52 4(3) . . . . ?
C50 C51 C52 C57 -8(3) . . . . ?
C42 C43 C53 C59 3.0(19) . . . . ?
C42 C43 C53 C54 179(2) . . . . ?
C45 C44 C54 C55 -1(2) . . . . ?
C45 C44 C54 C53 175.6(15) . . . . ?
C59 C53 C54 C44 -179.4(15) . . . . ?
C43 C53 C54 C44 5(3) . . . . ?
C59 C53 C54 C55 -3.1(16) . . . . ?
C43 C53 C54 C55 -179(2) . . . . ?
C46 C47 C55 N48 -177.4(12) . . . . ?
C46 C47 C55 C54 6.2(19) . . . . ?
C59 N48 C55 C47 179.9(13) . . . . ?
C56 N48 C55 C47 2(3) . . . . ?
C59 N48 C55 C54 -3.2(13) . . . . ?
C56 N48 C55 C54 178.7(15) . . . . ?
C44 C54 C55 C47 -2(2) . . . . ?
C53 C54 C55 C47 -178.8(13) . . . . ?
C44 C54 C55 N48 -179.1(12) . . . . ?
C53 C54 C55 N48 4.0(15) . . . . ?
C50 C49 C56 N48 178.7(13) . . . . ?
C50 C49 C56 C57 1(2) . . . . ?
C59 N48 C56 C49 -179.3(14) . . . . ?
C55 N48 C56 C49 -1(3) . . . . ?
C59 N48 C56 C57 -0.9(13) . . . . ?
C55 N48 C56 C57 177.2(15) . . . . ?
C51 C52 C57 C56 8(2) . . . . ?
C51 C52 C57 C58 -175.1(14) . . . . ?
C49 C56 C57 C52 -5(2) . . . . ?
N48 C56 C57 C52 176.9(12) . . . . ?
C49 C56 C57 C58 177.7(13) . . . . ?
N48 C56 C57 C58 -0.9(13) . . . . ?
C42 C41 C58 C59 4(2) . . . . ?
C42 C41 C58 C57 -174.6(16) . . . . ?
C52 C57 C58 C41 4(3) . . . . ?
C56 C57 C58 C41 -178.6(18) . . . . ?
C52 C57 C58 C59 -175.1(15) . . . . ?
C56 C57 C58 C59 2.3(14) . . . . ?
C41 C58 C59 N48 177.7(12) . . . . ?
C57 C58 C59 N48 -2.9(15) . . . . ?
C41 C58 C59 C53 1(2) . . . . ?
C57 C58 C59 C53 180.0(15) . . . . ?
C55 N48 C59 C58 -176.2(11) . . . . ?
C56 N48 C59 C58 2.5(15) . . . . ?
C55 N48 C59 C53 1.4(15) . . . . ?
C56 N48 C59 C53 -179.8(11) . . . . ?
C43 C53 C59 C58 -4(2) . . . . ?
C54 C53 C59 C58 178.1(14) . . . . ?
C43 C53 C59 N48 178.6(11) . . . . ?
C54 C53 C59 N48 1.0(16) . . . . ?
C78 C61 C62 C63 -3(3) . . . . ?
C61 C62 C63 C73 2(3) . . . . ?
C74 C64 C65 C66 9(2) . . . . ?
C64 C65 C66 C67 -10(3) . . . . ?
C65 C66 C67 C75 8(2) . . . . ?
C76 C69 C70 C71 5(2) . . . . ?
C69 C70 C71 C72 -4(2) . . . . ?
C70 C71 C72 C77 4(2) . . . . ?
C62 C63 C73 C79 0(2) . . . . ?
C62 C63 C73 C74 -172.3(16) . . . . ?
C65 C64 C74 C75 -8.0(19) . . . . ?
C65 C64 C74 C73 178.6(12) . . . . ?
C63 C73 C74 C64 -11(3) . . . . ?
C79 C73 C74 C64 176.2(13) . . . . ?
C63 C73 C74 C75 175(2) . . . . ?
C79 C73 C74 C75 2.0(13) . . . . ?
C79 N68 C75 C74 3.4(15) . . . . ?
C76 N68 C75 C74 -174.3(16) . . . . ?
C79 N68 C75 C67 177.9(14) . . . . ?
C76 N68 C75 C67 0(3) . . . . ?
C64 C74 C75 N68 -178.3(12) . . . . ?
C73 C74 C75 N68 -3.5(15) . . . . ?
C64 C74 C75 C67 7(2) . . . . ?
C73 C74 C75 C67 -178.5(12) . . . . ?
C66 C67 C75 N68 -179.6(14) . . . . ?
C66 C67 C75 C74 -5.6(19) . . . . ?
C70 C69 C76 N68 176.5(13) . . . . ?
C70 C69 C76 C77 -4.9(19) . . . . ?
C79 N68 C76 C69 179.8(13) . . . . ?
C75 N68 C76 C69 -3(3) . . . . ?
C79 N68 C76 C77 1.0(13) . . . . ?
C75 N68 C76 C77 178.7(18) . . . . ?
C71 C72 C77 C76 -4(2) . . . . ?
C71 C72 C77 C78 -176.6(15) . . . . ?
C69 C76 C77 C72 5.0(19) . . . . ?
N68 C76 C77 C72 -176.1(12) . . . . ?
C69 C76 C77 C78 179.1(11) . . . . ?
N68 C76 C77 C78 -1.9(14) . . . . ?
C62 C61 C78 C79 2(2) . . . . ?
C62 C61 C78 C77 176.5(17) . . . . ?
C72 C77 C78 C79 175.1(16) . . . . ?
C76 C77 C78 C79 2.1(14) . . . . ?
C72 C77 C78 C61 1(3) . . . . ?
C76 C77 C78 C61 -172.2(17) . . . . ?
C61 C78 C79 N68 174.5(11) . . . . ?
C77 C78 C79 N68 -1.6(14) . . . . ?
C61 C78 C79 C73 -1(2) . . . . ?
C77 C78 C79 C73 -176.8(14) . . . . ?
C75 N68 C79 C78 -178.2(11) . . . . ?
C76 N68 C79 C78 0.4(14) . . . . ?
C75 N68 C79 C73 -2.1(14) . . . . ?
C76 N68 C79 C73 176.6(10) . . . . ?
C63 C73 C79 C78 -1(2) . . . . ?
C74 C73 C79 C78 175.2(14) . . . . ?
C63 C73 C79 N68 -175.8(12) . . . . ?
C74 C73 C79 N68 0.0(13) . . . . ?

_refine_diff_density_max         0.990
_refine_diff_density_min         -0.485
_refine_diff_density_rms         0.158

####################################################################### 
# 
# 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_ICZTFBQ-100K
_database_code_depnum_ccdc_archive 'CCDC 2421754'
loop_
_audit_author_name
_audit_author_address
'Ruben A Toscano'
;Instituto de Quimica Universidad Nacional Autonoma de Mexico
Mexico
;
_audit_update_record             
;
2025-02-05 deposited with the CCDC.	2025-05-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H11 N, C6 F4 O2'
_chemical_formula_sum            'C24 H11 F4 N O2'
_chemical_formula_weight         421.34

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                   15.4910(6)
_cell_length_b                   6.8140(2)
_cell_length_c                   16.6374(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.2360(10)
_cell_angle_gamma                90
_cell_volume                     1755.76(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9769
_cell_measurement_theta_min      3.27
_cell_measurement_theta_max      29.16

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.359
_exptl_crystal_size_mid          0.356
_exptl_crystal_size_min          0.338
_exptl_absorpt_coefficient_mu    0.131
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6912
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   '(Sheldrick, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus X-ray source'
_diffrn_radiation_monochromator  'Helios multilayer mirror'
_diffrn_measurement_device_type  
'Bruker D8 Venture κ geometry diffractometer 208039-1'
_diffrn_measurement_method       'φ and ω-scans'
_diffrn_detector_area_resol_mean 52.0833
_diffrn_reflns_number            4797
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.231
_diffrn_reflns_theta_max         29.181
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4797
_reflns_number_gt                4214
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'APEX5 v2023.9-2-0(Bruker, 2023)'
_computing_cell_refinement       'APEX5 v2023.9-2(Bruker, 2023)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2014)'
_computing_structure_solution    'SHELXS-2012 (Bruker, 2013)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXLe (H?bschle et al, 2011)'
_computing_publication_material  'CIFTAB V 2013/2 (Sheldrick, 2013)'
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0371P)²+1.2476P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         4797
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0472
_refine_ls_wR_factor_ref         0.1131
_refine_ls_wR_factor_gt          0.1064
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_restrained_S_all      1.109
_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
C1 C 0.82998(12) 0.5364(3) 0.56268(12) 0.0192(4) Uani 1 1 d . . . . .
H1 H 0.881998 0.570768 0.590510 0.023 Uiso 1 1 calc R U . . .
C2 C 0.75721(13) 0.4747(3) 0.60467(11) 0.0211(4) Uani 1 1 d . . . . .
H2 H 0.761967 0.468396 0.661631 0.025 Uiso 1 1 calc R U . . .
C3 C 0.67782(13) 0.4214(3) 0.56849(12) 0.0204(4) Uani 1 1 d . . . . .
H3 H 0.630848 0.380765 0.600272 0.025 Uiso 1 1 calc R U . . .
C4 C 0.52386(12) 0.3282(3) 0.41128(12) 0.0200(4) Uani 1 1 d . . . . .
H4 H 0.492628 0.301023 0.458520 0.024 Uiso 1 1 calc R U . . .
C5 C 0.48512(12) 0.3043(3) 0.33574(13) 0.0229(4) Uani 1 1 d . . . . .
H5 H 0.426963 0.260516 0.331726 0.027 Uiso 1 1 calc R U . . .
C6 C 0.53013(12) 0.3434(3) 0.26562(13) 0.0225(4) Uani 1 1 d . . . . .
H6 H 0.501986 0.325251 0.214866 0.027 Uiso 1 1 calc R U . . .
C7 C 0.61542(12) 0.4085(3) 0.26857(11) 0.0184(4) Uani 1 1 d . . . . .
H7 H 0.646106 0.434637 0.220921 0.022 Uiso 1 1 calc R U . . .
N8 N 0.73753(9) 0.4952(2) 0.36530(8) 0.0147(3) Uani 1 1 d . . . . .
C9 C 0.84508(12) 0.5900(3) 0.25957(11) 0.0176(4) Uani 1 1 d . . . . .
H9 H 0.807622 0.569325 0.214394 0.021 Uiso 1 1 calc R U . . .
C10 C 0.92991(12) 0.6526(3) 0.25079(11) 0.0198(4) Uani 1 1 d . . . . .
H10 H 0.950767 0.673973 0.198230 0.024 Uiso 1 1 calc R U . . .
C11 C 0.98517(12) 0.6849(3) 0.31658(12) 0.0201(4) Uani 1 1 d . . . . .
H11 H 1.042619 0.727624 0.308025 0.024 Uiso 1 1 calc R U . . .
C12 C 0.95747(11) 0.6555(3) 0.39467(12) 0.0179(4) Uani 1 1 d . . . . .
H12 H 0.995433 0.678489 0.439290 0.021 Uiso 1 1 calc R U . . .
C13 C 0.82384(11) 0.5462(3) 0.47825(11) 0.0156(3) Uani 1 1 d . . . . .
C14 C 0.66940(11) 0.4296(3) 0.48429(11) 0.0157(3) Uani 1 1 d . . . . .
C15 C 0.60908(12) 0.3926(3) 0.41668(11) 0.0164(4) Uani 1 1 d . . . . .
C16 C 0.65351(11) 0.4335(3) 0.34389(11) 0.0148(3) Uani 1 1 d . . . . .
C17 C 0.81788(11) 0.5592(3) 0.33752(11) 0.0148(3) Uani 1 1 d . . . . .
C18 C 0.87311(11) 0.5918(3) 0.40643(11) 0.0144(3) Uani 1 1 d . . . . .
C19 C 0.74389(12) 0.4915(3) 0.44750(10) 0.0160(3) Uani 1 1 d . . . . .
F1 F 0.60395(7) 0.87653(18) 0.43842(8) 0.0246(3) Uani 1 1 d . . . . .
F2 F 0.68219(7) 0.94716(18) 0.29600(7) 0.0233(3) Uani 1 1 d . . . . .
F3 F 0.94065(7) 1.12736(17) 0.43724(7) 0.0220(2) Uani 1 1 d . . . . .
F4 F 0.86449(8) 1.04426(18) 0.57984(7) 0.0247(3) Uani 1 1 d . . . . .
O1 O 0.69626(10) 0.9297(2) 0.57761(9) 0.0243(3) Uani 1 1 d . . . . .
O2 O 0.84671(9) 1.0847(2) 0.29902(8) 0.0220(3) Uani 1 1 d . . . . .
C21 C 0.73097(12) 0.9606(3) 0.51409(11) 0.0182(4) Uani 1 1 d . . . . .
C22 C 0.68542(11) 0.9351(3) 0.43586(12) 0.0169(3) Uani 1 1 d . . . . .
C23 C 0.72380(12) 0.9708(3) 0.36596(11) 0.0166(3) Uani 1 1 d . . . . .
C24 C 0.81339(12) 1.0436(3) 0.36204(11) 0.0165(3) Uani 1 1 d . . . . .
C25 C 0.85942(12) 1.0661(3) 0.44039(12) 0.0166(3) Uani 1 1 d . . . . .
C26 C 0.82197(12) 1.0265(3) 0.50989(11) 0.0170(3) 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
C1 C2 1.404(3) . ?
C1 C13 1.407(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.405(3) . ?
C2 H2 0.9500 . ?
C3 C14 1.405(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(3) . ?
C4 C15 1.392(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.398(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.394(3) . ?
C6 H6 0.9500 . ?
C7 C16 1.384(3) . ?
C7 H7 0.9500 . ?
N8 C19 1.369(2) . ?
N8 C16 1.406(2) . ?
N8 C17 1.406(2) . ?
C9 C17 1.388(2) . ?
C9 C10 1.392(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.392(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.392(3) . ?
C11 H11 0.9500 . ?
C12 C18 1.395(2) . ?
C12 H12 0.9500 . ?
C13 C19 1.381(3) . ?
C13 C18 1.465(2) . ?
C14 C19 1.384(2) . ?
C14 C15 1.469(3) . ?
C15 C16 1.433(2) . ?
C17 C18 1.433(3) . ?
F1 C22 1.325(2) . ?
F2 C23 1.328(2) . ?
F3 C25 1.328(2) . ?
F4 C26 1.330(2) . ?
O1 C21 1.214(2) . ?
O2 C24 1.211(2) . ?
C21 C22 1.477(3) . ?
C21 C26 1.483(3) . ?
C22 C23 1.340(3) . ?
C23 C24 1.477(3) . ?
C24 C25 1.480(3) . ?
C25 C26 1.332(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
C2 C1 C13 118.24(17) . . ?
C2 C1 H1 120.9 . . ?
C13 C1 H1 120.9 . . ?
C1 C2 C3 124.69(17) . . ?
C1 C2 H2 117.7 . . ?
C3 C2 H2 117.7 . . ?
C2 C3 C14 118.58(17) . . ?
C2 C3 H3 120.7 . . ?
C14 C3 H3 120.7 . . ?
C5 C4 C15 119.04(18) . . ?
C5 C4 H4 120.5 . . ?
C15 C4 H4 120.5 . . ?
C4 C5 C6 121.25(17) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C7 C6 C5 121.39(19) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C16 C7 C6 117.16(18) . . ?
C16 C7 H7 121.4 . . ?
C6 C7 H7 121.4 . . ?
C19 N8 C16 107.08(14) . . ?
C19 N8 C17 106.79(14) . . ?
C16 N8 C17 146.14(15) . . ?
C17 C9 C10 116.77(17) . . ?
C17 C9 H9 121.6 . . ?
C10 C9 H9 121.6 . . ?
C11 C10 C9 122.12(17) . . ?
C11 C10 H10 118.9 . . ?
C9 C10 H10 118.9 . . ?
C12 C11 C10 120.97(17) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C18 118.97(17) . . ?
C11 C12 H12 120.5 . . ?
C18 C12 H12 120.5 . . ?
C19 C13 C1 113.44(16) . . ?
C19 C13 C18 103.53(15) . . ?
C1 C13 C18 143.02(18) . . ?
C19 C14 C3 113.13(17) . . ?
C19 C14 C15 103.68(15) . . ?
C3 C14 C15 143.18(17) . . ?
C4 C15 C16 118.61(17) . . ?
C4 C15 C14 133.66(17) . . ?
C16 C15 C14 107.72(15) . . ?
C7 C16 N8 129.81(16) . . ?
C7 C16 C15 122.54(16) . . ?
N8 C16 C15 107.64(15) . . ?
C9 C17 N8 129.97(16) . . ?
C9 C17 C18 122.42(16) . . ?
N8 C17 C18 107.61(14) . . ?
C12 C18 C17 118.75(16) . . ?
C12 C18 C13 133.36(17) . . ?
C17 C18 C13 107.89(15) . . ?
N8 C19 C13 114.18(15) . . ?
N8 C19 C14 113.88(16) . . ?
C13 C19 C14 131.92(16) . . ?
O1 C21 C22 122.29(18) . . ?
O1 C21 C26 122.20(19) . . ?
C22 C21 C26 115.51(16) . . ?
F1 C22 C23 121.55(18) . . ?
F1 C22 C21 116.37(16) . . ?
C23 C22 C21 122.07(17) . . ?
F2 C23 C22 121.51(17) . . ?
F2 C23 C24 116.16(16) . . ?
C22 C23 C24 122.30(18) . . ?
O2 C24 C23 122.29(18) . . ?
O2 C24 C25 122.16(17) . . ?
C23 C24 C25 115.54(16) . . ?
F3 C25 C26 121.91(17) . . ?
F3 C25 C24 115.89(16) . . ?
C26 C25 C24 122.20(17) . . ?
F4 C26 C25 121.61(17) . . ?
F4 C26 C21 116.08(16) . . ?
C25 C26 C21 122.31(18) . . ?

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
C13 C1 C2 C3 -0.1(3) . . . . ?
C1 C2 C3 C14 0.0(3) . . . . ?
C15 C4 C5 C6 0.1(3) . . . . ?
C4 C5 C6 C7 -0.2(3) . . . . ?
C5 C6 C7 C16 -0.3(3) . . . . ?
C17 C9 C10 C11 -0.5(3) . . . . ?
C9 C10 C11 C12 0.0(3) . . . . ?
C10 C11 C12 C18 0.3(3) . . . . ?
C2 C1 C13 C19 0.0(2) . . . . ?
C2 C1 C13 C18 -178.5(2) . . . . ?
C2 C3 C14 C19 0.1(2) . . . . ?
C2 C3 C14 C15 178.5(2) . . . . ?
C5 C4 C15 C16 0.6(3) . . . . ?
C5 C4 C15 C14 -178.65(19) . . . . ?
C19 C14 C15 C4 -180.0(2) . . . . ?
C3 C14 C15 C4 1.5(4) . . . . ?
C19 C14 C15 C16 0.74(18) . . . . ?
C3 C14 C15 C16 -177.8(2) . . . . ?
C6 C7 C16 N8 179.48(18) . . . . ?
C6 C7 C16 C15 0.9(3) . . . . ?
C19 N8 C16 C7 -178.64(19) . . . . ?
C17 N8 C16 C7 1.4(4) . . . . ?
C19 N8 C16 C15 0.1(2) . . . . ?
C17 N8 C16 C15 -179.9(2) . . . . ?
C4 C15 C16 C7 -1.1(3) . . . . ?
C14 C15 C16 C7 178.32(17) . . . . ?
C4 C15 C16 N8 -179.93(16) . . . . ?
C14 C15 C16 N8 -0.53(19) . . . . ?
C10 C9 C17 N8 -179.32(17) . . . . ?
C10 C9 C17 C18 0.8(3) . . . . ?
C19 N8 C17 C9 -179.32(19) . . . . ?
C16 N8 C17 C9 0.6(4) . . . . ?
C19 N8 C17 C18 0.62(19) . . . . ?
C16 N8 C17 C18 -179.4(2) . . . . ?
C11 C12 C18 C17 -0.1(3) . . . . ?
C11 C12 C18 C13 179.64(18) . . . . ?
C9 C17 C18 C12 -0.4(3) . . . . ?
N8 C17 C18 C12 179.61(15) . . . . ?
C9 C17 C18 C13 179.75(17) . . . . ?
N8 C17 C18 C13 -0.20(19) . . . . ?
C19 C13 C18 C12 179.94(19) . . . . ?
C1 C13 C18 C12 -1.4(4) . . . . ?
C19 C13 C18 C17 -0.29(19) . . . . ?
C1 C13 C18 C17 178.3(2) . . . . ?
C16 N8 C19 C13 179.16(15) . . . . ?
C17 N8 C19 C13 -0.9(2) . . . . ?
C16 N8 C19 C14 0.4(2) . . . . ?
C17 N8 C19 C14 -179.61(15) . . . . ?
C1 C13 C19 N8 -178.38(16) . . . . ?
C18 C13 C19 N8 0.7(2) . . . . ?
C1 C13 C19 C14 0.1(3) . . . . ?
C18 C13 C19 C14 179.18(19) . . . . ?
C3 C14 C19 N8 178.33(17) . . . . ?
C15 C14 C19 N8 -0.7(2) . . . . ?
C3 C14 C19 C13 -0.1(3) . . . . ?
C15 C14 C19 C13 -179.18(19) . . . . ?
O1 C21 C22 F1 0.1(3) . . . . ?
C26 C21 C22 F1 -179.89(14) . . . . ?
O1 C21 C22 C23 179.48(18) . . . . ?
C26 C21 C22 C23 -0.5(2) . . . . ?
F1 C22 C23 F2 -0.7(3) . . . . ?
C21 C22 C23 F2 179.92(16) . . . . ?
F1 C22 C23 C24 177.54(15) . . . . ?
C21 C22 C23 C24 -1.8(3) . . . . ?
F2 C23 C24 O2 1.9(3) . . . . ?
C22 C23 C24 O2 -176.45(19) . . . . ?
F2 C23 C24 C25 -179.00(16) . . . . ?
C22 C23 C24 C25 2.6(2) . . . . ?
O2 C24 C25 F3 -2.3(3) . . . . ?
C23 C24 C25 F3 178.58(15) . . . . ?
O2 C24 C25 C26 177.95(19) . . . . ?
C23 C24 C25 C26 -1.1(3) . . . . ?
F3 C25 C26 F4 -0.8(3) . . . . ?
C24 C25 C26 F4 178.90(16) . . . . ?
F3 C25 C26 C21 179.16(15) . . . . ?
C24 C25 C26 C21 -1.1(3) . . . . ?
O1 C21 C26 F4 2.0(2) . . . . ?
C22 C21 C26 F4 -178.04(16) . . . . ?
O1 C21 C26 C25 -177.98(19) . . . . ?
C22 C21 C26 C25 2.0(2) . . . . ?

_refine_diff_density_max         0.323
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.059

####################################################################### 
# 
# 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_ICZTCNQ-300K
_database_code_depnum_ccdc_archive 'CCDC 2421739'
loop_
_audit_author_name
_audit_author_address
'Ruben A Toscano'
;Instituto de Quimica Universidad Nacional Autonoma de Mexico
Mexico
;
_audit_update_record             
;
2025-02-05 deposited with the CCDC.	2025-05-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H15 N5'
_chemical_formula_weight         445.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0034 0.0017
'XDISP Program in WinGX S.Brennan & P.L.Cowan Rev.Sci.Instrum.63,850 1992'
H H 0.0000 0.0000
'XDISP Program in WinGX S.Brennan & P.L.Cowan Rev.Sci.Instrum.63,850 1992'
N N 0.0065 0.0035
'XDISP Program in WinGX S.Brennan & P.L.Cowan Rev.Sci.Instrum.63,850 1992'


_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                   9.2145(11)
_cell_length_b                   7.1841(9)
_cell_length_c                   33.492(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.263(4)
_cell_angle_gamma                90
_cell_volume                     2203.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    9892
_cell_measurement_theta_min      2.9744
_cell_measurement_theta_max      26.0483

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_F_000             920
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.938
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_process_details   'SADABS 2016/2 Bruker AXS Madison WI USA'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.7288
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source beamline 12.2.1'
_diffrn_measurement_device_type  'Bruker D8 with PHOTONII detector'
_diffrn_measurement_method       'ω/θ shutterless scans'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            49261
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_av_R_equivalents  0.0568
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         2.298
_diffrn_reflns_theta_max         26.098
_diffrn_reflns_theta_full        25.930
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4048
_reflns_number_gt                3358
_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       'Bruker APEX 3'
_computing_cell_refinement       'Bruker SAINT v8.40a'
_computing_data_reduction        'Bruker SAINT v8.40a'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL & local programs'
_refine_special_details          
;
 All non-hydrogen atoms were refined anisotropically. Hydrogen atoms
 were placed gemoetrically then constrained and  refined with a
 riding model. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0395P)²+0.5282P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'Dual space'
_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         4048
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.1006
_refine_ls_wR_factor_gt          0.0943
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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
N1 N 0.31988(11) 0.47889(16) 0.62427(3) 0.0404(3) Uani 1 1 d . . . . .
C1 C 0.28884(15) 0.41637(19) 0.66231(4) 0.0419(3) Uani 1 1 d . . . . .
C2 C 0.15691(17) 0.3932(2) 0.67746(5) 0.0576(4) Uani 1 1 d . . . . .
H2A H 0.069574 0.425797 0.662519 0.069 Uiso 1 1 calc R U . . .
C3 C 0.1590(2) 0.3197(3) 0.71567(5) 0.0739(5) Uani 1 1 d . . . . .
H3A H 0.071262 0.300332 0.726367 0.089 Uiso 1 1 calc R U . . .
C4 C 0.2891(2) 0.2744(3) 0.73841(5) 0.0728(5) Uani 1 1 d . . . . .
H4A H 0.287272 0.228165 0.764290 0.087 Uiso 1 1 calc R U . . .
C5 C 0.42089(18) 0.2968(2) 0.72320(4) 0.0568(4) Uani 1 1 d . . . . .
H5A H 0.507508 0.265301 0.738621 0.068 Uiso 1 1 calc R U . . .
C6 C 0.42336(15) 0.36661(19) 0.68472(4) 0.0425(3) Uani 1 1 d . . . . .
C7 C 0.53980(14) 0.39723(18) 0.65879(4) 0.0401(3) Uani 1 1 d . . . . .
C8 C 0.68958(15) 0.3781(2) 0.65728(4) 0.0464(3) Uani 1 1 d . . . . .
H8A H 0.749871 0.334038 0.679335 0.056 Uiso 1 1 calc R U . . .
C9 C 0.74696(15) 0.4269(2) 0.62169(4) 0.0488(4) Uani 1 1 d . . . . .
H9A H 0.846892 0.412026 0.620941 0.059 Uiso 1 1 calc R U . . .
C10 C 0.66579(15) 0.4962(2) 0.58720(4) 0.0455(3) Uani 1 1 d . . . . .
H10A H 0.710562 0.528684 0.564618 0.055 Uiso 1 1 calc R U . . .
C11 C 0.51541(14) 0.51512(18) 0.58779(4) 0.0386(3) Uani 1 1 d . . . . .
C12 C 0.46668(13) 0.46322(18) 0.62359(4) 0.0383(3) Uani 1 1 d . . . . .
C13 C 0.38196(14) 0.57294(18) 0.56309(4) 0.0396(3) Uani 1 1 d . . . . .
C14 C 0.35330(16) 0.6425(2) 0.52433(4) 0.0469(3) Uani 1 1 d . . . . .
H14A H 0.428884 0.659597 0.508423 0.056 Uiso 1 1 calc R U . . .
C15 C 0.21169(17) 0.6859(2) 0.50967(5) 0.0539(4) Uani 1 1 d . . . . .
H15A H 0.191897 0.731240 0.483640 0.065 Uiso 1 1 calc R U . . .
C16 C 0.09831(17) 0.6626(2) 0.53331(5) 0.0558(4) Uani 1 1 d . . . . .
H16A H 0.003898 0.693760 0.522749 0.067 Uiso 1 1 calc R U . . .
C17 C 0.12151(15) 0.5945(2) 0.57208(5) 0.0496(4) Uani 1 1 d . . . . .
H17A H 0.044889 0.579919 0.587725 0.060 Uiso 1 1 calc R U . . .
C18 C 0.26310(14) 0.54901(18) 0.58664(4) 0.0397(3) Uani 1 1 d . . . . .
C19 C 0.36406(14) 1.02266(18) 0.59215(4) 0.0398(3) Uani 1 1 d . . . . .
C20 C 0.51231(14) 1.02104(19) 0.58211(4) 0.0420(3) Uani 1 1 d . . . . .
H20A H 0.531183 1.059215 0.556656 0.050 Uiso 1 1 calc R U . . .
C21 C 0.62328(14) 0.9660(2) 0.60853(4) 0.0435(3) Uani 1 1 d . . . . .
H21A H 0.717988 0.968594 0.601382 0.052 Uiso 1 1 calc R U . . .
C22 C 0.59753(14) 0.90253(19) 0.64802(4) 0.0409(3) Uani 1 1 d . . . . .
C23 C 0.44941(14) 0.8995(2) 0.65778(4) 0.0429(3) Uani 1 1 d . . . . .
H23A H 0.430068 0.855984 0.682806 0.051 Uiso 1 1 calc R U . . .
C24 C 0.33829(14) 0.95845(19) 0.63145(4) 0.0422(3) Uani 1 1 d . . . . .
H24A H 0.243731 0.957675 0.638729 0.051 Uiso 1 1 calc R U . . .
C25 C 0.25166(14) 1.08323(19) 0.56492(4) 0.0424(3) Uani 1 1 d . . . . .
C26 C 0.27442(15) 1.1379(2) 0.52506(5) 0.0485(4) Uani 1 1 d . . . . .
N2 N 0.29193(16) 1.1783(2) 0.49300(4) 0.0683(4) Uani 1 1 d . . . . .
C27 C 0.10370(16) 1.0946(2) 0.57406(4) 0.0495(4) Uani 1 1 d . . . . .
N3 N -0.01512(15) 1.1083(2) 0.58041(5) 0.0716(4) Uani 1 1 d . . . . .
C28 C 0.71119(15) 0.8460(2) 0.67540(4) 0.0456(3) Uani 1 1 d . . . . .
C29 C 0.68861(15) 0.7751(2) 0.71421(5) 0.0519(4) Uani 1 1 d . . . . .
N4 N 0.67425(16) 0.7159(3) 0.74520(4) 0.0729(4) Uani 1 1 d . . . . .
C30 C 0.86014(16) 0.8497(2) 0.66710(4) 0.0559(4) Uani 1 1 d . . . . .
N5 N 0.98028(16) 0.8499(3) 0.66162(5) 0.0828(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
N1 C12 1.3600(16) . ?
N1 C18 1.4041(17) . ?
N1 C1 1.4093(17) . ?
C1 C2 1.3775(19) . ?
C1 C6 1.4230(19) . ?
C2 C3 1.383(2) . ?
C3 C4 1.387(3) . ?
C4 C5 1.377(2) . ?
C5 C6 1.385(2) . ?
C6 C7 1.4687(19) . ?
C7 C12 1.3766(18) . ?
C7 C8 1.3934(19) . ?
C8 C9 1.400(2) . ?
C9 C10 1.397(2) . ?
C10 C11 1.3946(18) . ?
C11 C12 1.3768(18) . ?
C11 C13 1.4654(18) . ?
C13 C14 1.3891(19) . ?
C13 C18 1.4283(19) . ?
C14 C15 1.379(2) . ?
C15 C16 1.388(2) . ?
C16 C17 1.382(2) . ?
C17 C18 1.3814(19) . ?
C19 C25 1.3738(19) . ?
C19 C24 1.4389(19) . ?
C19 C20 1.4419(18) . ?
C20 C21 1.3369(19) . ?
C21 C22 1.4429(19) . ?
C22 C28 1.3759(19) . ?
C22 C23 1.4378(18) . ?
C23 C24 1.3446(19) . ?
C25 C26 1.429(2) . ?
C25 C27 1.432(2) . ?
C26 N2 1.1404(19) . ?
C27 N3 1.1421(19) . ?
C28 C30 1.430(2) . ?
C28 C29 1.432(2) . ?
C29 N4 1.1427(19) . ?
C30 N5 1.1417(19) . ?

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
C12 N1 C18 106.78(11) . . ?
C12 N1 C1 106.80(11) . . ?
C18 N1 C1 146.42(11) . . ?
C2 C1 N1 130.23(13) . . ?
C2 C1 C6 121.89(13) . . ?
N1 C1 C6 107.81(11) . . ?
C1 C2 C3 117.60(15) . . ?
C2 C3 C4 121.47(16) . . ?
C5 C4 C3 120.91(16) . . ?
C4 C5 C6 119.42(15) . . ?
C5 C6 C1 118.68(13) . . ?
C5 C6 C7 133.75(13) . . ?
C1 C6 C7 107.51(11) . . ?
C12 C7 C8 113.39(12) . . ?
C12 C7 C6 103.72(11) . . ?
C8 C7 C6 142.85(13) . . ?
C7 C8 C9 118.27(13) . . ?
C10 C9 C8 125.10(13) . . ?
C11 C10 C9 117.78(13) . . ?
C12 C11 C10 113.89(12) . . ?
C12 C11 C13 103.60(11) . . ?
C10 C11 C13 142.51(13) . . ?
N1 C12 C7 114.14(12) . . ?
N1 C12 C11 114.31(11) . . ?
C7 C12 C11 131.55(12) . . ?
C14 C13 C18 118.71(12) . . ?
C14 C13 C11 133.78(13) . . ?
C18 C13 C11 107.50(11) . . ?
C15 C14 C13 119.35(14) . . ?
C14 C15 C16 120.77(14) . . ?
C17 C16 C15 121.97(14) . . ?
C18 C17 C16 117.32(14) . . ?
C17 C18 N1 130.31(13) . . ?
C17 C18 C13 121.87(13) . . ?
N1 C18 C13 107.81(11) . . ?
C25 C19 C24 121.40(12) . . ?
C25 C19 C20 120.84(13) . . ?
C24 C19 C20 117.75(12) . . ?
C21 C20 C19 121.59(13) . . ?
C20 C21 C22 120.64(12) . . ?
C28 C22 C23 121.10(13) . . ?
C28 C22 C21 120.99(12) . . ?
C23 C22 C21 117.91(12) . . ?
C24 C23 C22 121.34(13) . . ?
C23 C24 C19 120.73(12) . . ?
C19 C25 C26 122.03(12) . . ?
C19 C25 C27 122.87(13) . . ?
C26 C25 C27 115.09(12) . . ?
N2 C26 C25 178.70(17) . . ?
N3 C27 C25 177.71(17) . . ?
C22 C28 C30 122.81(13) . . ?
C22 C28 C29 122.31(13) . . ?
C30 C28 C29 114.88(12) . . ?
N4 C29 C28 178.07(17) . . ?
N5 C30 C28 177.81(17) . . ?

_refine_diff_density_max         0.148
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.032

####################################################################### 
# 
# 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_ICZTCNQ-100K
_database_code_depnum_ccdc_archive 'CCDC 2421740'
loop_
_audit_author_name
_audit_author_address
'Ruben A Toscano'
;Instituto de Quimica Universidad Nacional Autonoma de Mexico
Mexico
;
_audit_update_record             
;
2025-02-05 deposited with the CCDC.	2025-05-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H15 N5'
_chemical_formula_weight         445.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0034 0.0017
'XDISP Program in WinGX S.Brennan & P.L.Cowan Rev.Sci.Instrum.63,850 1992'
H H 0.0000 0.0000
'XDISP Program in WinGX S.Brennan & P.L.Cowan Rev.Sci.Instrum.63,850 1992'
N N 0.0065 0.0035
'XDISP Program in WinGX S.Brennan & P.L.Cowan Rev.Sci.Instrum.63,850 1992'

_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                   9.1770(9)
_cell_length_b                   7.0729(8)
_cell_length_c                   32.999(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.048(4)
_cell_angle_gamma                90
_cell_volume                     2130.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9422
_cell_measurement_theta_min      3.0211
_cell_measurement_theta_max      31.4103

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_F_000             920
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.957
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.950
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_process_details   'SADABS 2016/2 Bruker AXS Madison WI USA'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.7288
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source beamline 12.2.1'
_diffrn_measurement_device_type  'Bruker D8 with PHOTONII detector'
_diffrn_measurement_method       'ω/θ shutterless scans'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            69025
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_theta_min         1.273
_diffrn_reflns_theta_max         31.424
_diffrn_reflns_theta_full        25.930
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6508
_reflns_number_gt                5709
_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       'Bruker APEX 3'
_computing_cell_refinement       'Bruker SAINT v8.40a'
_computing_data_reduction        'Bruker SAINT v8.40a'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL & local programs'
_refine_special_details          
;
 All non-hydrogen atoms were refined anisotropically. Hydrogen atoms
 were placed gemoetrically then constrained and  refined with a
 riding model. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0587P)²+0.6716P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'Dual space'
_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         6508
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.1110
_refine_ls_wR_factor_gt          0.1066
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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
N1 N 0.31680(8) 0.47338(11) 0.62457(2) 0.01151(14) Uani 1 1 d . . . . .
C1 C 0.28444(9) 0.40813(13) 0.66297(3) 0.01214(16) Uani 1 1 d . . . . .
C2 C 0.15044(10) 0.38306(14) 0.67800(3) 0.01691(18) Uani 1 1 d . . . . .
H2A H 0.061391 0.417450 0.662428 0.020 Uiso 1 1 calc R U . . .
C3 C 0.15124(11) 0.30543(16) 0.71685(3) 0.0209(2) Uani 1 1 d . . . . .
H3A H 0.060789 0.284205 0.727707 0.025 Uiso 1 1 calc R U . . .
C4 C 0.28202(11) 0.25819(16) 0.74017(3) 0.0206(2) Uani 1 1 d . . . . .
H4A H 0.279126 0.208065 0.766786 0.025 Uiso 1 1 calc R U . . .
C5 C 0.41646(10) 0.28343(14) 0.72501(3) 0.01651(18) Uani 1 1 d . . . . .
H5A H 0.504943 0.251187 0.741107 0.020 Uiso 1 1 calc R U . . .
C6 C 0.41972(9) 0.35664(13) 0.68591(3) 0.01236(16) Uani 1 1 d . . . . .
C7 C 0.53737(9) 0.38809(12) 0.65971(3) 0.01180(16) Uani 1 1 d . . . . .
C8 C 0.68845(9) 0.36746(13) 0.65831(3) 0.01342(16) Uani 1 1 d . . . . .
H8A H 0.749556 0.320403 0.681114 0.016 Uiso 1 1 calc R U . . .
C9 C 0.74741(9) 0.41862(13) 0.62203(3) 0.01383(17) Uani 1 1 d . . . . .
H9A H 0.849854 0.402617 0.621238 0.017 Uiso 1 1 calc R U . . .
C10 C 0.66604(9) 0.49155(13) 0.58692(3) 0.01307(16) Uani 1 1 d . . . . .
H10A H 0.712360 0.525984 0.563575 0.016 Uiso 1 1 calc R U . . .
C11 C 0.51442(9) 0.51158(12) 0.58761(3) 0.01134(16) Uani 1 1 d . . . . .
C12 C 0.46440(9) 0.45714(12) 0.62399(3) 0.01161(16) Uani 1 1 d . . . . .
C13 C 0.38115(9) 0.57156(12) 0.56264(3) 0.01156(16) Uani 1 1 d . . . . .
C14 C 0.35374(10) 0.64361(13) 0.52323(3) 0.01377(17) Uani 1 1 d . . . . .
H14A H 0.431741 0.661102 0.506826 0.017 Uiso 1 1 calc R U . . .
C15 C 0.21078(10) 0.68953(13) 0.50826(3) 0.01565(17) Uani 1 1 d . . . . .
H15A H 0.191197 0.737810 0.481371 0.019 Uiso 1 1 calc R U . . .
C16 C 0.09537(10) 0.66541(13) 0.53236(3) 0.01623(18) Uani 1 1 d . . . . .
H16A H -0.001154 0.698799 0.521471 0.019 Uiso 1 1 calc R U . . .
C17 C 0.11808(10) 0.59384(13) 0.57185(3) 0.01451(17) Uani 1 1 d . . . . .
H17A H 0.039241 0.578193 0.588032 0.017 Uiso 1 1 calc R U . . .
C18 C 0.26059(9) 0.54635(12) 0.58657(3) 0.01163(16) Uani 1 1 d . . . . .
C19 C 0.36665(9) 1.01848(12) 0.59255(3) 0.01174(16) Uani 1 1 d . . . . .
C20 C 0.51502(9) 1.01836(13) 0.58172(3) 0.01270(16) Uani 1 1 d . . . . .
H20A H 0.533554 1.059700 0.555352 0.015 Uiso 1 1 calc R U . . .
C21 C 0.62782(9) 0.96056(13) 0.60837(3) 0.01303(16) Uani 1 1 d . . . . .
H21A H 0.724884 0.964473 0.600845 0.016 Uiso 1 1 calc R U . . .
C22 C 0.60186(9) 0.89258(12) 0.64841(3) 0.01190(16) Uani 1 1 d . . . . .
C23 C 0.45307(9) 0.88837(13) 0.65892(3) 0.01300(16) Uani 1 1 d . . . . .
H23A H 0.434011 0.841318 0.684810 0.016 Uiso 1 1 calc R U . . .
C24 C 0.34023(9) 0.95040(13) 0.63250(3) 0.01289(16) Uani 1 1 d . . . . .
H24A H 0.243382 0.949219 0.640215 0.015 Uiso 1 1 calc R U . . .
C25 C 0.25262(9) 1.08141(13) 0.56530(3) 0.01298(16) Uani 1 1 d . . . . .
C26 C 0.27516(10) 1.13852(13) 0.52472(3) 0.01460(17) Uani 1 1 d . . . . .
N2 N 0.29205(9) 1.18158(13) 0.49187(3) 0.02035(17) Uani 1 1 d . . . . .
C27 C 0.10433(10) 1.09251(13) 0.57492(3) 0.01496(17) Uani 1 1 d . . . . .
N3 N -0.01595(9) 1.10610(14) 0.58164(3) 0.02139(18) Uani 1 1 d . . . . .
C28 C 0.71658(9) 0.83201(13) 0.67570(3) 0.01339(16) Uani 1 1 d . . . . .
C29 C 0.69494(10) 0.75522(14) 0.71486(3) 0.01519(17) Uani 1 1 d . . . . .
N4 N 0.68158(9) 0.68971(14) 0.74620(3) 0.02070(18) Uani 1 1 d . . . . .
C30 C 0.86616(10) 0.83696(14) 0.66688(3) 0.01659(18) Uani 1 1 d . . . . .
N5 N 0.98753(9) 0.83713(15) 0.66105(3) 0.0247(2) 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
N1 C12 1.3616(11) . ?
N1 C18 1.4031(11) . ?
N1 C1 1.4093(11) . ?
C1 C2 1.3850(12) . ?
C1 C6 1.4315(12) . ?
C2 C3 1.3941(13) . ?
C3 C4 1.3963(14) . ?
C4 C5 1.3909(13) . ?
C5 C6 1.3935(12) . ?
C6 C7 1.4694(12) . ?
C7 C12 1.3820(12) . ?
C7 C8 1.3997(12) . ?
C8 C9 1.4120(12) . ?
C9 C10 1.4084(12) . ?
C10 C11 1.4011(12) . ?
C11 C12 1.3845(12) . ?
C11 C13 1.4637(12) . ?
C13 C14 1.3946(12) . ?
C13 C18 1.4365(12) . ?
C14 C15 1.3908(12) . ?
C15 C16 1.4003(13) . ?
C16 C17 1.3929(13) . ?
C17 C18 1.3875(12) . ?
C19 C25 1.3796(12) . ?
C19 C20 1.4437(12) . ?
C19 C24 1.4478(12) . ?
C20 C21 1.3493(12) . ?
C21 C22 1.4491(12) . ?
C22 C28 1.3795(12) . ?
C22 C23 1.4442(12) . ?
C23 C24 1.3545(12) . ?
C25 C27 1.4317(12) . ?
C25 C26 1.4346(12) . ?
C26 N2 1.1520(13) . ?
C27 N3 1.1525(12) . ?
C28 C30 1.4333(12) . ?
C28 C29 1.4347(12) . ?
C29 N4 1.1515(13) . ?
C30 N5 1.1501(13) . ?

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
C12 N1 C18 106.93(7) . . ?
C12 N1 C1 106.80(7) . . ?
C18 N1 C1 146.26(7) . . ?
C2 C1 N1 130.02(8) . . ?
C2 C1 C6 122.09(8) . . ?
N1 C1 C6 107.80(7) . . ?
C1 C2 C3 117.45(9) . . ?
C2 C3 C4 121.47(9) . . ?
C5 C4 C3 120.97(9) . . ?
C4 C5 C6 119.15(9) . . ?
C5 C6 C1 118.84(8) . . ?
C5 C6 C7 133.61(8) . . ?
C1 C6 C7 107.48(7) . . ?
C12 C7 C8 113.65(8) . . ?
C12 C7 C6 103.61(7) . . ?
C8 C7 C6 142.70(8) . . ?
C7 C8 C9 118.08(8) . . ?
C10 C9 C8 125.03(8) . . ?
C11 C10 C9 117.71(8) . . ?
C12 C11 C10 113.98(8) . . ?
C12 C11 C13 103.60(7) . . ?
C10 C11 C13 142.41(8) . . ?
N1 C12 C7 114.28(8) . . ?
N1 C12 C11 114.19(8) . . ?
C7 C12 C11 131.52(8) . . ?
C14 C13 C18 118.96(8) . . ?
C14 C13 C11 133.53(8) . . ?
C18 C13 C11 107.51(7) . . ?
C15 C14 C13 119.17(8) . . ?
C14 C15 C16 120.75(8) . . ?
C17 C16 C15 121.87(8) . . ?
C18 C17 C16 117.26(8) . . ?
C17 C18 N1 130.25(8) . . ?
C17 C18 C13 121.98(8) . . ?
N1 C18 C13 107.76(7) . . ?
C25 C19 C20 120.61(8) . . ?
C25 C19 C24 120.83(8) . . ?
C20 C19 C24 118.56(8) . . ?
C21 C20 C19 121.17(8) . . ?
C20 C21 C22 120.42(8) . . ?
C28 C22 C23 120.84(8) . . ?
C28 C22 C21 120.71(8) . . ?
C23 C22 C21 118.45(8) . . ?
C24 C23 C22 121.11(8) . . ?
C23 C24 C19 120.26(8) . . ?
C19 C25 C27 123.14(8) . . ?
C19 C25 C26 121.68(8) . . ?
C27 C25 C26 115.18(8) . . ?
N2 C26 C25 178.81(10) . . ?
N3 C27 C25 177.64(10) . . ?
C22 C28 C30 122.77(8) . . ?
C22 C28 C29 122.48(8) . . ?
C30 C28 C29 114.74(8) . . ?
N4 C29 C28 177.69(10) . . ?
N5 C30 C28 177.53(10) . . ?

_refine_diff_density_max         0.451
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.073

####################################################################### 
# 
# 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_ICZTFBQ-298K
_database_code_depnum_ccdc_archive 'CCDC 2421752'
loop_
_audit_author_name
_audit_author_address
'Ruben A Toscano'
;Instituto de Quimica Universidad Nacional Autonoma de Mexico
Mexico
;
_audit_update_record             
;
2025-02-05 deposited with the CCDC.	2025-05-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H11 N, C6 F4 O2'
_chemical_formula_sum            'C24 H11 F4 N O2'
_chemical_formula_weight         421.34

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      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 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, -z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'
'x-1/2, y-1/2, -z-1/2'

_cell_length_a                   7.0571(11)
_cell_length_b                   16.847(3)
_cell_length_c                   15.534(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1846.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9914
_cell_measurement_theta_min      2.89
_cell_measurement_theta_max      29.09

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.359
_exptl_crystal_size_mid          0.356
_exptl_crystal_size_min          0.338
_exptl_absorpt_coefficient_mu    0.124
_shelx_estimated_absorpt_T_min   0.957
_shelx_estimated_absorpt_T_max   0.959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7199
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   '(Sheldrick, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus X-ray source'
_diffrn_radiation_monochromator  'Helios multilayer mirror'
_diffrn_measurement_device_type  
'Bruker D8 Venture κ geometry diffractometer 208039-1'
_diffrn_measurement_method       'φ and ω-scans'
_diffrn_detector_area_resol_mean 52.0833
_diffrn_reflns_number            54036
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.130
_diffrn_reflns_theta_max         28.699
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             2373
_reflns_number_gt                1351
_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       'APEX5 v2023.9-2-0(Bruker, 2023)'
_computing_cell_refinement       'APEX5 v2023.9-2(Bruker, 2023)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2014)'
_computing_structure_solution    'SHELXS-2012 (Bruker, 2013)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXLe (Hübschle et al, 2011)'
_computing_publication_material  'CIFTAB V 2013/2 (Sheldrick, 2013)'
_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)+(0.0334P)²+0.6070P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.054(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2373
_refine_ls_number_parameters     305
_refine_ls_number_restraints     366
_refine_ls_R_factor_all          0.0953
_refine_ls_R_factor_gt           0.0487
_refine_ls_wR_factor_ref         0.1308
_refine_ls_wR_factor_gt          0.0979
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      0.990
_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
C1 C 0.500000 0.60127(19) 0.750000 0.1115(13) Uani 1 2 d S T P . .
H1 H 0.499999 0.656472 0.750001 0.134 Uiso 1 2 calc R U P . .
C2 C 0.5584(4) 0.56351(12) 0.67473(17) 0.0993(8) Uani 1 1 d . . . . .
H2 H 0.595300 0.592690 0.626758 0.119 Uiso 1 1 calc R U . . .
C3 C 0.5599(3) 0.48065(11) 0.67332(13) 0.0724(6) Uani 1 1 d . . . . .
C4 C 0.6021(3) 0.41181(12) 0.61919(12) 0.0698(5) Uani 1 1 d . . . . .
C5 C 0.6687(3) 0.40232(17) 0.53499(14) 0.0904(7) Uani 1 1 d . . . . .
H5 H 0.695477 0.446374 0.501017 0.108 Uiso 1 1 calc R U . . .
C6 C 0.6941(4) 0.32693(19) 0.50326(16) 0.1039(8) Uani 1 1 d . . . . .
H6 H 0.737176 0.320545 0.447108 0.125 Uiso 1 1 calc R U . . .
C7 C 0.6576(3) 0.26082(17) 0.55207(17) 0.1003(8) Uani 1 1 d . . . . .
H7 H 0.677676 0.210761 0.528537 0.120 Uiso 1 1 calc R U . . .
C8 C 0.5913(3) 0.26718(13) 0.63585(14) 0.0812(6) Uani 1 1 d . . . . .
H8 H 0.566169 0.222358 0.668878 0.097 Uiso 1 1 calc R U . . .
C9 C 0.5642(2) 0.34224(11) 0.66819(11) 0.0639(5) Uani 1 1 d . . . . .
N10 N 0.500000 0.36687(12) 0.750000 0.0644(6) Uani 1 2 d S T P . .
C11 C 0.500000 0.44836(14) 0.750000 0.0675(7) Uani 1 2 d S T P . .
F1 F 0.116(6) 0.4453(18) 0.5905(16) 0.168(13) Uani 0.25 1 d D . P A -1
F2 F 0.061(4) 0.5743(11) 0.6734(18) 0.124(8) Uani 0.25 1 d D . P A -1
F3 F -0.145(5) 0.4209(17) 0.9186(15) 0.124(8) Uani 0.25 1 d D . P A -1
F4 F -0.064(5) 0.2843(8) 0.8229(18) 0.115(7) Uani 0.25 1 d D . P A -1
O1 O 0.057(5) 0.3057(10) 0.6576(17) 0.079(5) Uani 0.25 1 d D U P A -1
O2 O -0.067(3) 0.5703(11) 0.8357(19) 0.079(4) Uani 0.25 1 d D U P A -1
C12 C 0.045(9) 0.3640(12) 0.705(2) 0.071(2) Uani 0.25 1 d D U P A -1
C13 C 0.063(5) 0.4440(9) 0.6716(14) 0.072(2) Uani 0.25 1 d D U P A -1
C14 C 0.048(5) 0.5040(10) 0.7111(16) 0.071(2) Uani 0.25 1 d D U P A -1
C15 C -0.024(5) 0.5070(10) 0.7993(15) 0.073(3) Uani 0.25 1 d D U P A -1
C16 C -0.076(5) 0.4209(8) 0.8390(14) 0.071(2) Uani 0.25 1 d D U P A -1
C17 C -0.030(8) 0.3574(11) 0.7909(18) 0.072(2) Uani 0.25 1 d D U P A -1
F1B F -0.126(4) 0.4305(12) 0.9260(10) 0.081(4) Uani 0.25 1 d D U P B -2
F2B F -0.041(3) 0.5668(10) 0.8637(8) 0.093(3) Uani 0.25 1 d D U P B -2
F3B F 0.138(4) 0.4400(12) 0.5969(9) 0.077(3) Uani 0.25 1 d D U P B -2
F4B F 0.065(4) 0.2944(9) 0.6767(14) 0.071(4) Uani 0.25 1 d D U P B -2
O1B O -0.111(4) 0.3006(11) 0.8339(16) 0.079(4) Uani 0.25 1 d D U P B -2
O2B O 0.071(4) 0.5799(11) 0.6988(14) 0.090(3) Uani 0.25 1 d D U P B -2
C12B C -0.043(8) 0.3616(11) 0.8040(19) 0.071(2) Uani 0.25 1 d D U P B -2
C13B C -0.063(5) 0.4375(9) 0.8467(16) 0.072(2) Uani 0.25 1 d D U P B -2
C14B C -0.030(4) 0.5011(9) 0.8173(10) 0.072(2) Uani 0.25 1 d D U P B -2
C15B C 0.030(4) 0.5134(8) 0.7283(11) 0.071(2) Uani 0.25 1 d D U P B -2
C16B C 0.074(6) 0.4319(9) 0.6768(16) 0.071(2) Uani 0.25 1 d D U P B -2
C17B C 0.031(7) 0.3638(11) 0.7175(18) 0.071(2) Uani 0.25 1 d D U P B -2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.393(3) . ?
C1 C2 1.393(3) 3_656 ?
C1 H1 0.9300 . ?
C2 C3 1.396(3) . ?
C2 H2 0.9300 . ?
C3 C11 1.376(2) . ?
C3 C4 1.463(3) . ?
C4 C5 1.399(3) . ?
C4 C9 1.423(2) . ?
C5 C6 1.374(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.372(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.387(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.374(3) . ?
C8 H8 0.9300 . ?
C9 N10 1.4118(19) . ?
N10 C11 1.373(3) . ?
F1 C13 1.32(3) . ?
F2 C14 1.325(19) . ?
F3 C16 1.33(3) . ?
F4 C17 1.35(2) . ?
O1 C12 1.23(2) . ?
O2 C15 1.243(19) . ?
C12 C17 1.442(7) . ?
C12 C13 1.448(17) . ?
C13 C14 1.19(2) . ?
C14 C15 1.462(7) . ?
C15 C16 1.62(2) . ?
C16 C17 1.345(17) . ?
F1B C13B 1.32(3) . ?
F2B C14B 1.324(19) . ?
F3B C16B 1.33(3) . ?
F4B C17B 1.352(19) . ?
O1B C12B 1.23(2) . ?
O2B C15B 1.244(19) . ?
C12B C17B 1.441(7) . ?
C12B C13B 1.447(17) . ?
C13B C14B 1.19(2) . ?
C14B C15B 1.460(8) . ?
C15B C16B 1.62(2) . ?
C16B C17B 1.345(17) . ?

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
C2 C1 C2 125.7(3) . 3_656 ?
C2 C1 H1 117.2 . . ?
C2 C1 H1 117.2 3_656 . ?
C1 C2 C3 118.2(2) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 H2 120.9 . . ?
C11 C3 C2 112.3(2) . . ?
C11 C3 C4 104.28(16) . . ?
C2 C3 C4 143.4(2) . . ?
C5 C4 C9 117.98(19) . . ?
C5 C4 C3 134.1(2) . . ?
C9 C4 C3 107.89(16) . . ?
C6 C5 C4 119.0(2) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C7 C6 C5 121.9(2) . . ?
C7 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?
C6 C7 C8 121.3(2) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C9 C8 C7 117.5(2) . . ?
C9 C8 H8 121.3 . . ?
C7 C8 H8 121.3 . . ?
C8 C9 N10 130.12(18) . . ?
C8 C9 C4 122.44(18) . . ?
N10 C9 C4 107.44(16) . . ?
C11 N10 C9 107.10(11) . . ?
C11 N10 C9 107.10(11) . 3_656 ?
C9 N10 C9 145.8(2) . 3_656 ?
N10 C11 C3 113.29(13) . . ?
N10 C11 C3 113.29(13) . 3_656 ?
C3 C11 C3 133.4(3) . 3_656 ?
O1 C12 C17 121(2) . . ?
O1 C12 C13 121.7(16) . . ?
C17 C12 C13 115.8(18) . . ?
C14 C13 F1 120.4(15) . . ?
C14 C13 C12 126.9(18) . . ?
F1 C13 C12 112.5(15) . . ?
C13 C14 F2 121.8(18) . . ?
C13 C14 C15 123.0(18) . . ?
F2 C14 C15 114.1(14) . . ?
O2 C15 C14 122.6(15) . . ?
O2 C15 C16 122.7(15) . . ?
C14 C15 C16 113.9(15) . . ?
F3 C16 C17 127.3(15) . . ?
F3 C16 C15 115.9(12) . . ?
C17 C16 C15 116.5(13) . . ?
C16 C17 F4 118.6(12) . . ?
C16 C17 C12 122.8(19) . . ?
F4 C17 C12 118.5(17) . . ?
O1B C12B C17B 121(2) . . ?
O1B C12B C13B 121.9(15) . . ?
C17B C12B C13B 116.1(17) . . ?
C14B C13B F1B 120.5(14) . . ?
C14B C13B C12B 126.9(17) . . ?
F1B C13B C12B 112.5(15) . . ?
C13B C14B F2B 122.2(15) . . ?
C13B C14B C15B 123.4(17) . . ?
F2B C14B C15B 114.4(13) . . ?
O2B C15B C14B 122.9(15) . . ?
O2B C15B C16B 122.5(14) . . ?
C14B C15B C16B 113.7(13) . . ?
F3B C16B C17B 127.2(15) . . ?
F3B C16B C15B 116.1(11) . . ?
C17B C16B C15B 116.6(13) . . ?
C16B C17B F4B 118.4(11) . . ?
C16B C17B C12B 122.8(18) . . ?
F4B C17B C12B 118.7(16) . . ?

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
C2 C1 C2 C3 -0.12(14) 3_656 . . . ?
C1 C2 C3 C11 0.2(3) . . . . ?
C1 C2 C3 C4 -180.0(2) . . . . ?
C11 C3 C4 C5 -179.66(19) . . . . ?
C2 C3 C4 C5 0.5(4) . . . . ?
C11 C3 C4 C9 -0.10(17) . . . . ?
C2 C3 C4 C9 -179.9(3) . . . . ?
C9 C4 C5 C6 0.2(3) . . . . ?
C3 C4 C5 C6 179.7(2) . . . . ?
C4 C5 C6 C7 -0.6(4) . . . . ?
C5 C6 C7 C8 0.6(4) . . . . ?
C6 C7 C8 C9 -0.2(3) . . . . ?
C7 C8 C9 N10 -179.70(16) . . . . ?
C7 C8 C9 C4 -0.2(3) . . . . ?
C5 C4 C9 C8 0.2(3) . . . . ?
C3 C4 C9 C8 -179.43(17) . . . . ?
C5 C4 C9 N10 179.81(14) . . . . ?
C3 C4 C9 N10 0.16(18) . . . . ?
C8 C9 N10 C11 179.39(17) . . . . ?
C4 C9 N10 C11 -0.17(13) . . . . ?
C8 C9 N10 C9 -0.61(17) . . . 3_656 ?
C4 C9 N10 C9 179.83(13) . . . 3_656 ?
C9 N10 C11 C3 0.11(11) . . . . ?
C9 N10 C11 C3 -179.89(11) 3_656 . . . ?
C9 N10 C11 C3 -179.89(11) . . . 3_656 ?
C9 N10 C11 C3 0.11(11) 3_656 . . 3_656 ?
C2 C3 C11 N10 179.88(13) . . . . ?
C4 C3 C11 N10 -0.01(14) . . . . ?
C2 C3 C11 C3 -0.11(13) . . . 3_656 ?
C4 C3 C11 C3 180.00(14) . . . 3_656 ?
O1 C12 C13 C14 177(5) . . . . ?
C17 C12 C13 C14 11(8) . . . . ?
O1 C12 C13 F1 -8(8) . . . . ?
C17 C12 C13 F1 -174(5) . . . . ?
F1 C13 C14 F2 8(6) . . . . ?
C12 C13 C14 F2 -178(4) . . . . ?
F1 C13 C14 C15 175(3) . . . . ?
C12 C13 C14 C15 -11(6) . . . . ?
C13 C14 C15 O2 -169(5) . . . . ?
F2 C14 C15 O2 -1(3) . . . . ?
C13 C14 C15 C16 1(4) . . . . ?
F2 C14 C15 C16 170(3) . . . . ?
O2 C15 C16 F3 -9(5) . . . . ?
C14 C15 C16 F3 -179(3) . . . . ?
O2 C15 C16 C17 177(4) . . . . ?
C14 C15 C16 C17 6(5) . . . . ?
F3 C16 C17 F4 3(7) . . . . ?
C15 C16 C17 F4 177(4) . . . . ?
F3 C16 C17 C12 -180(5) . . . . ?
C15 C16 C17 C12 -6(7) . . . . ?
O1 C12 C17 C16 -168(6) . . . . ?
C13 C12 C17 C16 -2(8) . . . . ?
O1 C12 C17 F4 9(9) . . . . ?
C13 C12 C17 F4 175(5) . . . . ?
O1B C12B C13B C14B -167(5) . . . . ?
C17B C12B C13B C14B 2(7) . . . . ?
O1B C12B C13B F1B 12(6) . . . . ?
C17B C12B C13B F1B -178(5) . . . . ?
F1B C13B C14B F2B 5(5) . . . . ?
C12B C13B C14B F2B -176(4) . . . . ?
F1B C13B C14B C15B -176(3) . . . . ?
C12B C13B C14B C15B 3(5) . . . . ?
C13B C14B C15B O2B -177(3) . . . . ?
F2B C14B C15B O2B 2(4) . . . . ?
C13B C14B C15B C16B -8(4) . . . . ?
F2B C14B C15B C16B 171(2) . . . . ?
O2B C15B C16B F3B -7(5) . . . . ?
C14B C15B C16B F3B -177(3) . . . . ?
O2B C15B C16B C17B 177(4) . . . . ?
C14B C15B C16B C17B 7(4) . . . . ?
F3B C16B C17B F4B 5(7) . . . . ?
C15B C16B C17B F4B 180(4) . . . . ?
F3B C16B C17B C12B -178(5) . . . . ?
C15B C16B C17B C12B -3(7) . . . . ?
O1B C12B C17B C16B 167(4) . . . . ?
C13B C12B C17B C16B -2(8) . . . . ?
O1B C12B C17B F4B -15(9) . . . . ?
C13B C12B C17B F4B 175(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C8 H8 O2B 0.93 2.63 3.50(2) 155.4 6_655 yes

_refine_diff_density_max         0.140
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.026

####################################################################### 
# 
# 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_ICZTFBQ-200K
_database_code_depnum_ccdc_archive 'CCDC 2421742'
loop_
_audit_author_name
_audit_author_address
'Ruben A Toscano'
;Instituto de Quimica Universidad Nacional Autonoma de Mexico
Mexico
;
_audit_update_record             
;
2025-02-05 deposited with the CCDC.	2025-05-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H11 N, C6 F4 O2'
_chemical_formula_sum            'C24 H11 F4 N O2'
_chemical_formula_weight         421.34

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                   15.5166(8)
_cell_length_b                   6.9014(3)
_cell_length_c                   16.7105(10)
_cell_angle_alpha                90
_cell_angle_beta                 90.931(2)
_cell_angle_gamma                90
_cell_volume                     1789.23(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9876
_cell_measurement_theta_min      3.23
_cell_measurement_theta_max      29.15

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.359
_exptl_crystal_size_mid          0.356
_exptl_crystal_size_min          0.338
_exptl_absorpt_coefficient_mu    0.128
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.958
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6842
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   '(Sheldrick, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus X-ray source'
_diffrn_radiation_monochromator  'Helios multilayer mirror'
_diffrn_measurement_device_type  
'Bruker D8 Venture κ geometry diffractometer 208039-1'
_diffrn_measurement_method       'φ and ω-scans'
_diffrn_detector_area_resol_mean 52.0833
_diffrn_reflns_number            4838
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.194
_diffrn_reflns_theta_max         29.225
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4838
_reflns_number_gt                3549
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'APEX5 v2023.9-2-0(Bruker, 2023)'
_computing_cell_refinement       'APEX5 v2023.9-2(Bruker, 2023)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2014)'
_computing_structure_solution    'SHELXS-2012 (Bruker, 2013)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXLe (Hübschle et al, 2011)'
_computing_publication_material  'CIFTAB V 2013/2 (Sheldrick, 2013)'
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0265P)²+1.0443P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         4838
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0865
_refine_ls_R_factor_gt           0.0543
_refine_ls_wR_factor_ref         0.1236
_refine_ls_wR_factor_gt          0.1090
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_restrained_S_all      1.139
_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
C1 C 0.82878(18) 0.5388(4) 0.56208(16) 0.0429(6) Uani 1 1 d . . . . .
H1 H 0.880158 0.573824 0.590189 0.051 Uiso 1 1 calc R U . . .
C2 C 0.7560(2) 0.4766(4) 0.60299(15) 0.0481(7) Uani 1 1 d . . . . .
H2 H 0.760270 0.470034 0.659702 0.058 Uiso 1 1 calc R U . . .
C3 C 0.67751(18) 0.4233(4) 0.56750(16) 0.0442(6) Uani 1 1 d . . . . .
H3 H 0.630448 0.383157 0.599168 0.053 Uiso 1 1 calc R U . . .
C4 C 0.52565(16) 0.3273(4) 0.41067(18) 0.0438(6) Uani 1 1 d . . . . .
H4 H 0.494157 0.299368 0.457563 0.053 Uiso 1 1 calc R U . . .
C5 C 0.48790(17) 0.3037(4) 0.3355(2) 0.0517(7) Uani 1 1 d . . . . .
H5 H 0.430027 0.259423 0.331341 0.062 Uiso 1 1 calc R U . . .
C6 C 0.53297(17) 0.3433(4) 0.26626(19) 0.0482(7) Uani 1 1 d . . . . .
H6 H 0.505425 0.324882 0.215643 0.058 Uiso 1 1 calc R U . . .
C7 C 0.61758(15) 0.4094(4) 0.26957(15) 0.0384(5) Uani 1 1 d . . . . .
H7 H 0.648421 0.436591 0.222222 0.046 Uiso 1 1 calc R U . . .
N8 N 0.73883(12) 0.4964(3) 0.36569(10) 0.0317(4) Uani 1 1 d . . . . .
C9 C 0.84666(15) 0.5901(4) 0.26072(14) 0.0358(5) Uani 1 1 d . . . . .
H9 H 0.809652 0.569248 0.215690 0.043 Uiso 1 1 calc R U . . .
C10 C 0.93115(16) 0.6523(4) 0.25216(16) 0.0424(6) Uani 1 1 d . . . . .
H10 H 0.952455 0.672743 0.199861 0.051 Uiso 1 1 calc R U . . .
C11 C 0.98540(16) 0.6855(4) 0.31747(17) 0.0434(6) Uani 1 1 d . . . . .
H11 H 1.042641 0.728805 0.308976 0.052 Uiso 1 1 calc R U . . .
C12 C 0.95748(15) 0.6565(4) 0.39505(17) 0.0384(6) Uani 1 1 d . . . . .
H12 H 0.995118 0.679537 0.439442 0.046 Uiso 1 1 calc R U . . .
C13 C 0.82373(15) 0.5479(3) 0.47820(15) 0.0335(5) Uani 1 1 d . . . . .
C14 C 0.66995(15) 0.4306(3) 0.48362(15) 0.0350(5) Uani 1 1 d . . . . .
C15 C 0.61042(15) 0.3926(3) 0.41636(15) 0.0348(5) Uani 1 1 d . . . . .
C16 C 0.65495(14) 0.4338(3) 0.34430(15) 0.0315(5) Uani 1 1 d . . . . .
C17 C 0.81889(14) 0.5599(3) 0.33845(14) 0.0299(5) Uani 1 1 d . . . . .
C18 C 0.87343(14) 0.5933(3) 0.40673(14) 0.0308(5) Uani 1 1 d . . . . .
C19 C 0.74434(15) 0.4927(4) 0.44783(12) 0.0318(5) Uani 1 1 d . . . . .
F1 F 0.60288(9) 0.8752(2) 0.43817(11) 0.0539(4) Uani 1 1 d . . . . .
F2 F 0.68108(10) 0.9456(3) 0.29646(9) 0.0514(4) Uani 1 1 d . . . . .
F3 F 0.93748(9) 1.1285(2) 0.43609(10) 0.0496(4) Uani 1 1 d . . . . .
F4 F 0.86170(12) 1.0457(3) 0.57799(9) 0.0575(5) Uani 1 1 d . . . . .
O1 O 0.69426(14) 0.9313(3) 0.57639(11) 0.0533(5) Uani 1 1 d . . . . .
O2 O 0.84411(12) 1.0850(3) 0.29876(11) 0.0474(5) Uani 1 1 d . . . . .
C21 C 0.72888(18) 0.9619(4) 0.51258(15) 0.0408(6) Uani 1 1 d . . . . .
C22 C 0.68408(15) 0.9348(3) 0.43552(16) 0.0366(5) Uani 1 1 d . . . . .
C23 C 0.72226(16) 0.9708(4) 0.36616(15) 0.0359(5) Uani 1 1 d . . . . .
C24 C 0.81093(16) 1.0437(3) 0.36209(15) 0.0355(5) Uani 1 1 d . . . . .
C25 C 0.85660(16) 1.0672(4) 0.43932(16) 0.0370(5) Uani 1 1 d . . . . .
C26 C 0.81930(17) 1.0274(4) 0.50861(15) 0.0375(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
C1 C2 1.398(4) . ?
C1 C13 1.404(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.395(4) . ?
C2 H2 0.9500 . ?
C3 C14 1.406(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(4) . ?
C4 C15 1.392(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.389(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.390(3) . ?
C6 H6 0.9500 . ?
C7 C16 1.379(3) . ?
C7 H7 0.9500 . ?
N8 C19 1.374(3) . ?
N8 C17 1.400(3) . ?
N8 C16 1.412(3) . ?
C9 C10 1.389(3) . ?
C9 C17 1.391(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.386(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.388(4) . ?
C11 H11 0.9500 . ?
C12 C18 1.392(3) . ?
C12 H12 0.9500 . ?
C13 C19 1.378(3) . ?
C13 C18 1.466(3) . ?
C14 C19 1.377(3) . ?
C14 C15 1.467(4) . ?
C15 C16 1.427(3) . ?
C17 C18 1.428(3) . ?
F1 C22 1.327(3) . ?
F2 C23 1.331(3) . ?
F3 C25 1.327(3) . ?
F4 C26 1.330(3) . ?
O1 C21 1.220(3) . ?
O2 C24 1.218(3) . ?
C21 C22 1.465(4) . ?
C21 C26 1.476(4) . ?
C22 C23 1.334(3) . ?
C23 C24 1.467(3) . ?
C24 C25 1.471(4) . ?
C25 C26 1.332(4) . ?

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
C2 C1 C13 118.0(3) . . ?
C2 C1 H1 121.0 . . ?
C13 C1 H1 121.0 . . ?
C3 C2 C1 125.4(2) . . ?
C3 C2 H2 117.3 . . ?
C1 C2 H2 117.3 . . ?
C2 C3 C14 118.2(2) . . ?
C2 C3 H3 120.9 . . ?
C14 C3 H3 120.9 . . ?
C5 C4 C15 119.0(3) . . ?
C5 C4 H4 120.5 . . ?
C15 C4 H4 120.5 . . ?
C4 C5 C6 121.4(2) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C7 121.3(3) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C16 C7 C6 117.3(2) . . ?
C16 C7 H7 121.3 . . ?
C6 C7 H7 121.3 . . ?
C19 N8 C17 106.82(19) . . ?
C19 N8 C16 106.82(19) . . ?
C17 N8 C16 146.36(19) . . ?
C10 C9 C17 116.7(2) . . ?
C10 C9 H9 121.6 . . ?
C17 C9 H9 121.6 . . ?
C11 C10 C9 122.1(2) . . ?
C11 C10 H10 118.9 . . ?
C9 C10 H10 118.9 . . ?
C10 C11 C12 121.1(2) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C11 C12 C18 118.9(2) . . ?
C11 C12 H12 120.5 . . ?
C18 C12 H12 120.5 . . ?
C19 C13 C1 113.0(2) . . ?
C19 C13 C18 103.8(2) . . ?
C1 C13 C18 143.3(2) . . ?
C19 C14 C3 112.8(2) . . ?
C19 C14 C15 104.2(2) . . ?
C3 C14 C15 143.0(2) . . ?
C4 C15 C16 118.5(2) . . ?
C4 C15 C14 133.8(2) . . ?
C16 C15 C14 107.7(2) . . ?
C7 C16 N8 129.7(2) . . ?
C7 C16 C15 122.5(2) . . ?
N8 C16 C15 107.7(2) . . ?
C9 C17 N8 129.8(2) . . ?
C9 C17 C18 122.2(2) . . ?
N8 C17 C18 107.94(18) . . ?
C12 C18 C17 118.9(2) . . ?
C12 C18 C13 133.5(2) . . ?
C17 C18 C13 107.68(19) . . ?
N8 C19 C14 113.6(2) . . ?
N8 C19 C13 113.8(2) . . ?
C14 C19 C13 132.6(2) . . ?
O1 C21 C22 122.4(3) . . ?
O1 C21 C26 121.6(3) . . ?
C22 C21 C26 115.9(2) . . ?
F1 C22 C23 121.5(3) . . ?
F1 C22 C21 116.6(2) . . ?
C23 C22 C21 121.9(2) . . ?
F2 C23 C22 121.5(2) . . ?
F2 C23 C24 116.2(2) . . ?
C22 C23 C24 122.3(3) . . ?
O2 C24 C23 122.0(3) . . ?
O2 C24 C25 122.1(2) . . ?
C23 C24 C25 115.8(2) . . ?
F3 C25 C26 121.7(3) . . ?
F3 C25 C24 116.2(2) . . ?
C26 C25 C24 122.0(2) . . ?
F4 C26 C25 121.5(2) . . ?
F4 C26 C21 116.5(2) . . ?
C25 C26 C21 121.9(3) . . ?

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
C13 C1 C2 C3 -0.5(4) . . . . ?
C1 C2 C3 C14 0.4(4) . . . . ?
C15 C4 C5 C6 0.2(4) . . . . ?
C4 C5 C6 C7 -0.4(4) . . . . ?
C5 C6 C7 C16 0.0(4) . . . . ?
C17 C9 C10 C11 -0.8(4) . . . . ?
C9 C10 C11 C12 0.4(4) . . . . ?
C10 C11 C12 C18 -0.1(4) . . . . ?
C2 C1 C13 C19 0.3(3) . . . . ?
C2 C1 C13 C18 -178.4(3) . . . . ?
C2 C3 C14 C19 -0.3(3) . . . . ?
C2 C3 C14 C15 178.4(3) . . . . ?
C5 C4 C15 C16 0.4(4) . . . . ?
C5 C4 C15 C14 -178.9(3) . . . . ?
C19 C14 C15 C4 179.9(3) . . . . ?
C3 C14 C15 C4 1.2(5) . . . . ?
C19 C14 C15 C16 0.6(2) . . . . ?
C3 C14 C15 C16 -178.1(3) . . . . ?
C6 C7 C16 N8 179.4(2) . . . . ?
C6 C7 C16 C15 0.5(4) . . . . ?
C19 N8 C16 C7 -179.0(2) . . . . ?
C17 N8 C16 C7 0.6(6) . . . . ?
C19 N8 C16 C15 0.0(3) . . . . ?
C17 N8 C16 C15 179.6(3) . . . . ?
C4 C15 C16 C7 -0.7(3) . . . . ?
C14 C15 C16 C7 178.7(2) . . . . ?
C4 C15 C16 N8 -179.8(2) . . . . ?
C14 C15 C16 N8 -0.4(2) . . . . ?
C10 C9 C17 N8 -179.3(2) . . . . ?
C10 C9 C17 C18 0.9(3) . . . . ?
C19 N8 C17 C9 -179.4(2) . . . . ?
C16 N8 C17 C9 1.0(6) . . . . ?
C19 N8 C17 C18 0.4(3) . . . . ?
C16 N8 C17 C18 -179.2(3) . . . . ?
C11 C12 C18 C17 0.1(4) . . . . ?
C11 C12 C18 C13 179.6(2) . . . . ?
C9 C17 C18 C12 -0.6(3) . . . . ?
N8 C17 C18 C12 179.6(2) . . . . ?
C9 C17 C18 C13 179.8(2) . . . . ?
N8 C17 C18 C13 -0.1(2) . . . . ?
C19 C13 C18 C12 -179.9(3) . . . . ?
C1 C13 C18 C12 -1.1(5) . . . . ?
C19 C13 C18 C17 -0.3(2) . . . . ?
C1 C13 C18 C17 178.4(3) . . . . ?
C17 N8 C19 C14 -179.4(2) . . . . ?
C16 N8 C19 C14 0.4(3) . . . . ?
C17 N8 C19 C13 -0.7(3) . . . . ?
C16 N8 C19 C13 179.1(2) . . . . ?
C3 C14 C19 N8 178.6(2) . . . . ?
C15 C14 C19 N8 -0.6(3) . . . . ?
C3 C14 C19 C13 0.2(4) . . . . ?
C15 C14 C19 C13 -179.0(3) . . . . ?
C1 C13 C19 N8 -178.6(2) . . . . ?
C18 C13 C19 N8 0.6(3) . . . . ?
C1 C13 C19 C14 -0.2(4) . . . . ?
C18 C13 C19 C14 179.0(3) . . . . ?
O1 C21 C22 F1 0.2(3) . . . . ?
C26 C21 C22 F1 179.7(2) . . . . ?
O1 C21 C22 C23 179.3(3) . . . . ?
C26 C21 C22 C23 -1.2(3) . . . . ?
F1 C22 C23 F2 -1.0(4) . . . . ?
C21 C22 C23 F2 179.9(2) . . . . ?
F1 C22 C23 C24 177.7(2) . . . . ?
C21 C22 C23 C24 -1.3(4) . . . . ?
F2 C23 C24 O2 2.4(3) . . . . ?
C22 C23 C24 O2 -176.4(3) . . . . ?
F2 C23 C24 C25 -178.8(2) . . . . ?
C22 C23 C24 C25 2.4(3) . . . . ?
O2 C24 C25 F3 -2.7(4) . . . . ?
C23 C24 C25 F3 178.4(2) . . . . ?
O2 C24 C25 C26 177.9(3) . . . . ?
C23 C24 C25 C26 -0.9(3) . . . . ?
F3 C25 C26 F4 -0.6(4) . . . . ?
C24 C25 C26 F4 178.7(2) . . . . ?
F3 C25 C26 C21 179.0(2) . . . . ?
C24 C25 C26 C21 -1.6(4) . . . . ?
O1 C21 C26 F4 1.9(3) . . . . ?
C22 C21 C26 F4 -177.6(2) . . . . ?
O1 C21 C26 C25 -177.8(3) . . . . ?
C22 C21 C26 C25 2.7(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C9 H9 F4 0.95 2.58 3.206(3) 124.1 4_575 yes

_refine_diff_density_max         0.272
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.051

