# Supplementary Information (SI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

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

data_AC-Toluene_solvate_100K
_database_code_depnum_ccdc_archive 'CCDC 2351862'
loop_
_audit_author_name
_audit_author_address
'Ruben Alfredo Toscano'
;Institute of Chemistry, National Autonomous University of Mexico
Mexico
;
_audit_update_record             
;
2024-04-26 deposited with the CCDC.	2024-08-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H24 N2'
_chemical_formula_weight         436.53

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   13.8355(8)
_cell_length_b                   10.5769(6)
_cell_length_c                   17.1587(13)
_cell_angle_alpha                90
_cell_angle_beta                 112.5690(10)
_cell_angle_gamma                90
_cell_volume                     2318.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6111
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      32.70

_exptl_crystal_description       prism
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_F_000             920
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.402
_exptl_crystal_size_mid          0.392
_exptl_crystal_size_min          0.364
_exptl_absorpt_coefficient_mu    0.073
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6770
_exptl_absorpt_correction_T_max  0.7464
_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                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 83.333
_diffrn_reflns_number            13471
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.500
_diffrn_reflns_theta_max         30.507
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3540
_reflns_number_gt                2879
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX3 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    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0710P)²+0.8400P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3540
_refine_ls_number_parameters     188
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.1327
_refine_ls_wR_factor_gt          0.1237
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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
C14 C 0.8005(2) 0.3098(2) 0.50477(16) 0.0306(5) Uani 0.5 1 d . . P A -1
C15 C 0.7608(4) 0.3245(5) 0.5657(3) 0.0385(10) Uani 0.5 1 d . . P A -1
H15 H 0.787992 0.389842 0.606302 0.046 Uiso 0.5 1 calc R U P A -1
C16 C 0.6817(2) 0.2473(4) 0.5705(2) 0.0564(9) Uani 0.5 1 d . . P A -1
H16 H 0.654293 0.260090 0.612955 0.068 Uiso 0.5 1 calc R U P A -1
C17 C 0.6445(3) 0.1524(5) 0.5123(3) 0.0660(14) Uani 0.5 1 d . . P A -1
H17 H 0.590644 0.098744 0.514587 0.079 Uiso 0.5 1 calc R U P A -1
C18 C 0.6830(3) 0.1331(3) 0.4510(2) 0.0554(9) Uani 0.5 1 d . . P A -1
H18 H 0.656107 0.066119 0.411631 0.066 Uiso 0.5 1 calc R U P A -1
C19 C 0.7633(5) 0.2128(5) 0.4456(4) 0.0392(11) Uani 0.5 1 d . . P A -1
H19 H 0.790539 0.200355 0.403077 0.047 Uiso 0.5 1 calc R U P A -1
C20 C 0.8842(4) 0.3961(4) 0.5011(3) 0.0534(9) Uani 0.5 1 d . . P A -1
H20A H 0.895861 0.380048 0.449102 0.080 Uiso 0.5 1 calc R U P A -1
H20B H 0.949190 0.380792 0.549996 0.080 Uiso 0.5 1 calc R U P A -1
H20C H 0.862364 0.484140 0.501661 0.080 Uiso 0.5 1 calc R U P A -1
N1 N 0.500000 0.53482(10) 0.750000 0.0175(2) Uani 1 2 d S T P . .
N2 N 0.500000 0.93578(11) 0.750000 0.0207(2) Uani 1 2 d S T P . .
C1 C 0.47006(7) 0.45763(8) 0.67854(6) 0.01714(19) Uani 1 1 d . . . . .
C2 C 0.43200(8) 0.49334(9) 0.59398(6) 0.0223(2) Uani 1 1 d . . . . .
H2 H 0.425492 0.579755 0.577681 0.027 Uiso 1 1 calc R U . . .
C3 C 0.40401(9) 0.39681(10) 0.53458(6) 0.0274(2) Uani 1 1 d . . . . .
H3 H 0.377658 0.417698 0.476283 0.033 Uiso 1 1 calc R U . . .
C4 C 0.41368(9) 0.26946(10) 0.55857(7) 0.0279(2) Uani 1 1 d . . . . .
H4 H 0.393647 0.205723 0.516318 0.033 Uiso 1 1 calc R U . . .
C5 C 0.45200(8) 0.23477(9) 0.64291(7) 0.0226(2) Uani 1 1 d . . . . .
H5 H 0.458665 0.148131 0.658711 0.027 Uiso 1 1 calc R U . . .
C6 C 0.48065(7) 0.32973(9) 0.70427(6) 0.01715(19) Uani 1 1 d . . . . .
C7 C 0.500000 0.66879(12) 0.750000 0.0159(2) Uani 1 2 d S T P . .
C8 C 0.57123(7) 0.73475(9) 0.72520(5) 0.01704(19) Uani 1 1 d . . . . .
C9 C 0.64805(8) 0.67405(10) 0.70157(6) 0.0215(2) Uani 1 1 d . . . . .
H9 H 0.652048 0.584376 0.701742 0.026 Uiso 1 1 calc R U . . .
C10 C 0.71569(8) 0.74399(11) 0.67876(7) 0.0276(2) Uani 1 1 d . . . . .
H10 H 0.766655 0.702591 0.663320 0.033 Uiso 1 1 calc R U . . .
C11 C 0.71077(9) 0.87835(11) 0.67783(8) 0.0307(3) Uani 1 1 d . . . . .
H11 H 0.757782 0.925751 0.660978 0.037 Uiso 1 1 calc R U . . .
C12 C 0.63937(8) 0.93964(10) 0.70085(7) 0.0267(2) Uani 1 1 d . . . . .
H12 H 0.637394 1.029424 0.700323 0.032 Uiso 1 1 calc R U . . .
C13 C 0.56727(7) 0.87027(9) 0.72582(6) 0.0191(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
C14 C15 1.365(7) . ?
C14 C19 1.395(6) . ?
C14 C20 1.495(4) . ?
C15 C16 1.393(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.370(7) . ?
C16 H16 0.9500 . ?
C17 C18 1.364(7) . ?
C17 H17 0.9500 . ?
C18 C19 1.426(6) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
N1 C1 1.3970(11) . ?
N1 C1 1.3970(11) 2_656 ?
N1 C7 1.4170(16) . ?
N2 C13 1.3471(11) 2_656 ?
N2 C13 1.3471(11) . ?
C1 C2 1.3924(13) . ?
C1 C6 1.4130(12) . ?
C2 C3 1.3886(14) . ?
C2 H2 0.9500 . ?
C3 C4 1.3998(15) . ?
C3 H3 0.9500 . ?
C4 C5 1.3861(15) . ?
C4 H4 0.9500 . ?
C5 C6 1.3979(13) . ?
C5 H5 0.9500 . ?
C6 C6 1.4507(18) 2_656 ?
C7 C8 1.4004(11) 2_656 ?
C7 C8 1.4004(11) . ?
C8 C9 1.4272(13) . ?
C8 C13 1.4346(13) . ?
C9 C10 1.3629(14) . ?
C9 H9 0.9500 . ?
C10 C11 1.4225(16) . ?
C10 H10 0.9500 . ?
C11 C12 1.3607(16) . ?
C11 H11 0.9500 . ?
C12 C13 1.4301(14) . ?
C12 H12 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 C14 C19 119.8(4) . . ?
C15 C14 C20 120.6(4) . . ?
C19 C14 C20 119.6(4) . . ?
C14 C15 C16 122.4(5) . . ?
C14 C15 H15 118.8 . . ?
C16 C15 H15 118.8 . . ?
C17 C16 C15 118.0(4) . . ?
C17 C16 H16 121.0 . . ?
C15 C16 H16 121.0 . . ?
C18 C17 C16 121.7(4) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C17 C18 C19 120.4(4) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C14 C19 C18 117.8(5) . . ?
C14 C19 H19 121.1 . . ?
C18 C19 H19 121.1 . . ?
C14 C20 H20A 109.5 . . ?
C14 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C14 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C1 N1 C1 108.48(10) . 2_656 ?
C1 N1 C7 125.76(5) . . ?
C1 N1 C7 125.76(5) 2_656 . ?
C13 N2 C13 118.10(11) 2_656 . ?
C2 C1 N1 128.48(9) . . ?
C2 C1 C6 122.52(8) . . ?
N1 C1 C6 108.97(8) . . ?
C3 C2 C1 116.93(9) . . ?
C3 C2 H2 121.5 . . ?
C1 C2 H2 121.5 . . ?
C2 C3 C4 121.57(10) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 121.12(9) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 118.71(9) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C5 C6 C1 119.15(9) . . ?
C5 C6 C6 134.03(6) . 2_656 ?
C1 C6 C6 106.79(5) . 2_656 ?
C8 C7 C8 120.24(11) 2_656 . ?
C8 C7 N1 119.88(6) 2_656 . ?
C8 C7 N1 119.88(6) . . ?
C7 C8 C9 123.36(9) . . ?
C7 C8 C13 117.53(9) . . ?
C9 C8 C13 119.10(8) . . ?
C10 C9 C8 120.38(9) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 120.68(10) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C12 C11 C10 120.64(10) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 120.67(10) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
N2 C13 C12 118.18(9) . . ?
N2 C13 C8 123.30(9) . . ?
C12 C13 C8 118.51(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C19 C14 C15 C16 -1.3(8) . . . . ?
C20 C14 C15 C16 179.0(4) . . . . ?
C14 C15 C16 C17 1.0(7) . . . . ?
C15 C16 C17 C18 -0.1(6) . . . . ?
C16 C17 C18 C19 -0.5(6) . . . . ?
C15 C14 C19 C18 0.7(8) . . . . ?
C20 C14 C19 C18 -179.6(4) . . . . ?
C17 C18 C19 C14 0.1(7) . . . . ?
C1 N1 C1 C2 178.09(12) 2_656 . . . ?
C7 N1 C1 C2 -1.91(12) . . . . ?
C1 N1 C1 C6 0.11(5) 2_656 . . . ?
C7 N1 C1 C6 -179.89(5) . . . . ?
N1 C1 C2 C3 -177.58(9) . . . . ?
C6 C1 C2 C3 0.15(15) . . . . ?
C1 C2 C3 C4 -0.07(16) . . . . ?
C2 C3 C4 C5 -0.16(18) . . . . ?
C3 C4 C5 C6 0.31(17) . . . . ?
C4 C5 C6 C1 -0.22(15) . . . . ?
C4 C5 C6 C6 177.65(13) . . . 2_656 ?
C2 C1 C6 C5 0.00(14) . . . . ?
N1 C1 C6 C5 178.12(8) . . . . ?
C2 C1 C6 C6 -178.41(10) . . . 2_656 ?
N1 C1 C6 C6 -0.29(12) . . . 2_656 ?
C1 N1 C7 C8 111.74(6) . . . 2_656 ?
C1 N1 C7 C8 -68.26(6) 2_656 . . 2_656 ?
C1 N1 C7 C8 -68.27(6) . . . . ?
C1 N1 C7 C8 111.73(6) 2_656 . . . ?
C8 C7 C8 C9 178.07(10) 2_656 . . . ?
N1 C7 C8 C9 -1.92(10) . . . . ?
C8 C7 C8 C13 -0.44(6) 2_656 . . . ?
N1 C7 C8 C13 179.56(6) . . . . ?
C7 C8 C9 C10 -179.42(8) . . . . ?
C13 C8 C9 C10 -0.93(14) . . . . ?
C8 C9 C10 C11 -0.20(16) . . . . ?
C9 C10 C11 C12 0.93(18) . . . . ?
C10 C11 C12 C13 -0.49(17) . . . . ?
C13 N2 C13 C12 -179.45(10) 2_656 . . . ?
C13 N2 C13 C8 -0.49(6) 2_656 . . . ?
C11 C12 C13 N2 178.37(9) . . . . ?
C11 C12 C13 C8 -0.64(15) . . . . ?
C7 C8 C13 N2 0.96(12) . . . . ?
C9 C8 C13 N2 -177.62(7) . . . . ?
C7 C8 C13 C12 179.91(7) . . . . ?
C9 C8 C13 C12 1.33(13) . . . . ?

_refine_diff_density_max         0.392
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.045


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Toluene'
_chemical_properties_physical    Heat-sensitive
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_AC-PFBA_300K
_database_code_depnum_ccdc_archive 'CCDC 2351865'
loop_
_audit_author_name
_audit_author_address
'Ruben Alfredo Toscano'
;Institute of Chemistry, National Autonomous University of Mexico
Mexico
;
_audit_update_record             
;
2024-04-26 deposited with the CCDC.	2024-08-14 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         'C25 H16 N2, C7 H F5 O2'
_chemical_formula_sum            'C32 H17 F5 N2 O2'
_chemical_formula_weight         556.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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                   22.6117(3)
_cell_length_b                   8.39190(10)
_cell_length_c                   13.2304(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.8810(10)
_cell_angle_gamma                90
_cell_volume                     2507.36(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9762
_cell_measurement_theta_min      5.6241
_cell_measurement_theta_max      71.9561

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_F_000             1136
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.402
_exptl_crystal_size_mid          0.398
_exptl_crystal_size_min          0.388
_exptl_absorpt_coefficient_mu    1.010
_shelx_estimated_absorpt_T_min   0.687
_shelx_estimated_absorpt_T_max   0.695
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6209
_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            40172
_diffrn_reflns_av_unetI/netI     0.0144
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.915
_diffrn_reflns_theta_max         70.054
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             4711
_reflns_number_gt                4447
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX3 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)+(0.0529P)²+0.5498P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0042(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4711
_refine_ls_number_parameters     393
_refine_ls_number_restraints     270
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.1037
_refine_ls_wR_factor_gt          0.1020
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.014
_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
C1 C 0.81679(7) 0.96936(18) 0.48191(11) 0.0532(3) Uani 1 1 d . U . . .
H1 H 0.779823 0.920606 0.480232 0.064 Uiso 1 1 calc R U . . .
C2 C 0.83765(8) 1.0441(2) 0.39737(11) 0.0616(4) Uani 1 1 d . U . . .
H2 H 0.814147 1.045598 0.337639 0.074 Uiso 1 1 calc R U . . .
C3 C 0.89293(8) 1.1169(2) 0.39985(12) 0.0659(4) Uani 1 1 d . U . . .
H3 H 0.905738 1.166083 0.341885 0.079 Uiso 1 1 calc R U . . .
C4 C 0.92897(7) 1.11714(19) 0.48672(12) 0.0609(4) Uani 1 1 d . U . . .
H4 H 0.965950 1.165756 0.487590 0.073 Uiso 1 1 calc R U . . .
C5 C 0.98693(6) 1.0695(2) 0.72669(13) 0.0647(4) Uani 1 1 d . U . . .
H5 H 1.015603 1.125200 0.693137 0.078 Uiso 1 1 calc R U . . .
C6 C 0.99602(7) 1.0307(3) 0.82693(14) 0.0741(5) Uani 1 1 d . U . . .
H6 H 1.031233 1.060466 0.861116 0.089 Uiso 1 1 calc R U . . .
C7 C 0.95381(7) 0.9480(2) 0.87837(13) 0.0665(4) Uani 1 1 d . U . . .
H7 H 0.961317 0.923620 0.946368 0.080 Uiso 1 1 calc R U . . .
C8 C 0.90102(6) 0.90126(19) 0.83105(11) 0.0545(3) Uani 1 1 d . U . . .
H8 H 0.872658 0.845934 0.865582 0.065 Uiso 1 1 calc R U . . .
N9 N 0.84334(4) 0.90774(13) 0.66455(8) 0.0450(3) Uani 1 1 d . U . . .
C10 C 0.85351(5) 0.97045(15) 0.56924(10) 0.0436(3) Uani 1 1 d . U . . .
C11 C 0.90937(6) 1.04351(16) 0.57369(10) 0.0476(3) Uani 1 1 d . U . . .
C12 C 0.93403(6) 1.02413(16) 0.67566(11) 0.0483(3) Uani 1 1 d . U . . .
C13 C 0.89204(5) 0.94033(16) 0.72965(10) 0.0440(3) Uani 1 1 d . U . . .
C14 C 0.75900(6) 1.06166(16) 0.78890(11) 0.0496(3) Uani 1 1 d . U . . .
H14 H 0.792421 1.119441 0.773232 0.060 Uiso 1 1 calc R U . . .
C15 C 0.71775(7) 1.12918(18) 0.84603(12) 0.0586(4) Uani 1 1 d . U . . .
H15 H 0.723021 1.233289 0.868823 0.070 Uiso 1 1 calc R U . . .
C16 C 0.66683(7) 1.0436(2) 0.87146(12) 0.0616(4) Uani 1 1 d . U . . .
H16 H 0.639182 1.091371 0.911445 0.074 Uiso 1 1 calc R U . . .
C17 C 0.65793(6) 0.89304(19) 0.83827(11) 0.0566(4) Uani 1 1 d . U . . .
H17 H 0.624048 0.838466 0.855324 0.068 Uiso 1 1 calc R U . . .
C18 C 0.71624(7) 0.43669(17) 0.65383(13) 0.0600(4) Uani 1 1 d . U . . .
H18 H 0.681411 0.386626 0.670811 0.072 Uiso 1 1 calc R U . . .
C19 C 0.75532(8) 0.35808(19) 0.59857(13) 0.0676(4) Uani 1 1 d . U . . .
H19 H 0.747199 0.253935 0.578232 0.081 Uiso 1 1 calc R U . . .
C20 C 0.80838(8) 0.4312(2) 0.57105(13) 0.0662(4) Uani 1 1 d . U . . .
H20 H 0.834870 0.374788 0.533130 0.079 Uiso 1 1 calc R U . . .
C21 C 0.82098(6) 0.58324(18) 0.59954(11) 0.0545(3) Uani 1 1 d . U . . .
H21 H 0.855967 0.630487 0.580689 0.065 Uiso 1 1 calc R U . . .
C22 C 0.79142(5) 0.82642(15) 0.69176(9) 0.0405(3) Uani 1 1 d . U . . .
N23 N 0.68869(5) 0.66820(13) 0.74379(9) 0.0485(3) Uani 1 1 d . U . . .
C24 C 0.69962(6) 0.81680(16) 0.77763(10) 0.0446(3) Uani 1 1 d . U . . .
C25 C 0.75157(5) 0.90314(15) 0.75272(9) 0.0416(3) Uani 1 1 d . U . . .
C26 C 0.78116(5) 0.67086(15) 0.65795(9) 0.0428(3) Uani 1 1 d . U . . .
C27 C 0.72783(6) 0.59541(15) 0.68633(10) 0.0456(3) Uani 1 1 d . U . . .
F1 F 0.47371(4) 0.66161(10) 0.60149(8) 0.0698(3) Uani 1 1 d . U . . .
F2 F 0.58304(5) 0.61813(13) 0.54302(8) 0.0806(3) Uani 1 1 d . U . . .
F3 F 0.66056(4) 0.86311(16) 0.54507(8) 0.0829(3) Uani 1 1 d . U . . .
F4 F 0.62715(5) 1.15324(16) 0.60910(9) 0.0936(4) Uani 1 1 d . U . . .
F5 F 0.51686(5) 1.20469(11) 0.66282(8) 0.0791(3) Uani 1 1 d . U . . .
C31 C 0.49041(6) 0.93485(16) 0.63550(9) 0.0449(3) Uani 1 1 d . U . . .
C32 C 0.50964(6) 0.78709(16) 0.60312(10) 0.0485(3) Uani 1 1 d . U . . .
C33 C 0.56629(6) 0.76237(18) 0.57326(11) 0.0547(3) Uani 1 1 d . U . . .
C34 C 0.60557(6) 0.8856(2) 0.57481(11) 0.0584(4) Uani 1 1 d . U . . .
C35 C 0.58863(7) 1.0332(2) 0.60734(11) 0.0606(4) Uani 1 1 d . U . . .
C36 C 0.53165(7) 1.05680(17) 0.63668(10) 0.0525(3) Uani 1 1 d . U . . .
C37 C 0.42705(6) 0.95912(16) 0.66188(10) 0.0472(3) Uani 1 1 d . U . . .
O1 O 0.42035(10) 1.0618(4) 0.7337(3) 0.0668(8) Uani 0.863(10) 1 d . U P A 1
H1A H 0.3821(11) 1.087(3) 0.7344(18) 0.100 Uiso 1 1 d . U . B 1
O2 O 0.38650(8) 0.8932(3) 0.6156(2) 0.0665(7) Uani 0.863(10) 1 d . U P A 1
O1B O 0.4190(7) 1.0964(17) 0.6909(18) 0.061(4) Uani 0.137(10) 1 d . U P A 2
O2B O 0.3968(6) 0.8509(18) 0.672(3) 0.085(6) Uani 0.137(10) 1 d . U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.386(2) . ?
C1 C10 1.3884(19) . ?
C1 H1 0.9300 . ?
C2 C3 1.390(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.375(2) . ?
C3 H3 0.9300 . ?
C4 C11 1.398(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.371(3) . ?
C5 C12 1.397(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.386(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.377(2) . ?
C7 H7 0.9300 . ?
C8 C13 1.386(2) . ?
C8 H8 0.9300 . ?
N9 C13 1.3906(16) . ?
N9 C10 1.3961(16) . ?
N9 C22 1.4200(15) . ?
C10 C11 1.4026(18) . ?
C11 C12 1.443(2) . ?
C12 C13 1.4052(18) . ?
C14 C15 1.354(2) . ?
C14 C25 1.4210(18) . ?
C14 H14 0.9300 . ?
C15 C16 1.412(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.349(2) . ?
C16 H16 0.9300 . ?
C17 C24 1.4204(19) . ?
C17 H17 0.9300 . ?
C18 C19 1.347(2) . ?
C18 C27 1.4199(19) . ?
C18 H18 0.9300 . ?
C19 C20 1.412(2) . ?
C19 H19 0.9300 . ?
C20 C21 1.357(2) . ?
C20 H20 0.9300 . ?
C21 C26 1.4208(19) . ?
C21 H21 0.9300 . ?
C22 C26 1.3956(18) . ?
C22 C25 1.3963(18) . ?
N23 C27 1.3424(18) . ?
N23 C24 1.3437(18) . ?
C24 C25 1.4327(17) . ?
C26 C27 1.4289(18) . ?
F1 C32 1.3296(16) . ?
F2 C33 1.3356(17) . ?
F3 C34 1.3363(17) . ?
F4 C35 1.3309(18) . ?
F5 C36 1.3355(17) . ?
C31 C36 1.3841(19) . ?
C31 C32 1.3889(19) . ?
C31 C37 1.5053(18) . ?
C32 C33 1.375(2) . ?
C33 C34 1.363(2) . ?
C34 C35 1.372(2) . ?
C35 C36 1.379(2) . ?
C37 O2B 1.149(13) . ?
C37 O2 1.211(2) . ?
C37 O1B 1.231(15) . ?
C37 O1 1.298(3) . ?
O1 H1A 0.89(2) . ?

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 C10 117.08(14) . . ?
C2 C1 H1 121.5 . . ?
C10 C1 H1 121.5 . . ?
C1 C2 C3 121.46(15) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 H2 119.3 . . ?
C4 C3 C2 120.99(14) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C11 119.23(14) . . ?
C3 C4 H4 120.4 . . ?
C11 C4 H4 120.4 . . ?
C6 C5 C12 119.08(15) . . ?
C6 C5 H5 120.5 . . ?
C12 C5 H5 120.5 . . ?
C5 C6 C7 121.37(14) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C8 C7 C6 121.48(16) . . ?
C8 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C7 C8 C13 117.00(14) . . ?
C7 C8 H8 121.5 . . ?
C13 C8 H8 121.5 . . ?
C13 N9 C10 108.91(10) . . ?
C13 N9 C22 125.21(11) . . ?
C10 N9 C22 125.87(10) . . ?
C1 C10 N9 129.09(12) . . ?
C1 C10 C11 122.50(12) . . ?
N9 C10 C11 108.40(11) . . ?
C4 C11 C10 118.74(14) . . ?
C4 C11 C12 134.10(13) . . ?
C10 C11 C12 107.15(11) . . ?
C5 C12 C13 118.35(14) . . ?
C5 C12 C11 134.65(13) . . ?
C13 C12 C11 107.01(11) . . ?
C8 C13 N9 128.75(12) . . ?
C8 C13 C12 122.73(12) . . ?
N9 C13 C12 108.53(11) . . ?
C15 C14 C25 120.45(13) . . ?
C15 C14 H14 119.8 . . ?
C25 C14 H14 119.8 . . ?
C14 C15 C16 120.86(14) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C17 C16 C15 120.59(14) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C24 120.88(14) . . ?
C16 C17 H17 119.6 . . ?
C24 C17 H17 119.6 . . ?
C19 C18 C27 120.50(14) . . ?
C19 C18 H18 119.8 . . ?
C27 C18 H18 119.8 . . ?
C18 C19 C20 121.08(15) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 H19 119.5 . . ?
C21 C20 C19 120.44(15) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C21 C26 120.51(14) . . ?
C20 C21 H21 119.7 . . ?
C26 C21 H21 119.7 . . ?
C26 C22 C25 120.98(11) . . ?
C26 C22 N9 119.64(11) . . ?
C25 C22 N9 119.38(11) . . ?
C27 N23 C24 119.71(11) . . ?
N23 C24 C17 119.34(12) . . ?
N23 C24 C25 122.13(12) . . ?
C17 C24 C25 118.51(12) . . ?
C22 C25 C14 123.88(12) . . ?
C22 C25 C24 117.39(12) . . ?
C14 C25 C24 118.71(12) . . ?
C22 C26 C21 123.97(12) . . ?
C22 C26 C27 117.33(12) . . ?
C21 C26 C27 118.69(12) . . ?
N23 C27 C18 118.78(12) . . ?
N23 C27 C26 122.43(12) . . ?
C18 C27 C26 118.78(13) . . ?
C36 C31 C32 116.25(12) . . ?
C36 C31 C37 123.09(12) . . ?
C32 C31 C37 120.58(12) . . ?
F1 C32 C33 116.95(13) . . ?
F1 C32 C31 120.76(12) . . ?
C33 C32 C31 122.28(13) . . ?
F2 C33 C34 119.87(13) . . ?
F2 C33 C32 120.33(14) . . ?
C34 C33 C32 119.79(14) . . ?
F3 C34 C33 120.22(15) . . ?
F3 C34 C35 119.91(15) . . ?
C33 C34 C35 119.86(13) . . ?
F4 C35 C34 119.72(15) . . ?
F4 C35 C36 120.44(16) . . ?
C34 C35 C36 119.83(14) . . ?
F5 C36 C35 117.13(14) . . ?
F5 C36 C31 120.84(13) . . ?
C35 C36 C31 121.98(14) . . ?
O2B C37 O1B 127.3(8) . . ?
O2 C37 O1 124.13(18) . . ?
O2B C37 C31 120.0(6) . . ?
O2 C37 C31 121.75(14) . . ?
O1B C37 C31 110.8(7) . . ?
O1 C37 C31 114.03(16) . . ?
C37 O1 H1A 108.3(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
C10 C1 C2 C3 0.1(2) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C2 C3 C4 C11 -0.3(2) . . . . ?
C12 C5 C6 C7 -0.2(3) . . . . ?
C5 C6 C7 C8 0.0(3) . . . . ?
C6 C7 C8 C13 0.1(3) . . . . ?
C2 C1 C10 N9 178.63(14) . . . . ?
C2 C1 C10 C11 0.2(2) . . . . ?
C13 N9 C10 C1 -178.52(13) . . . . ?
C22 N9 C10 C1 0.4(2) . . . . ?
C13 N9 C10 C11 0.12(14) . . . . ?
C22 N9 C10 C11 179.02(12) . . . . ?
C3 C4 C11 C10 0.4(2) . . . . ?
C3 C4 C11 C12 -178.52(15) . . . . ?
C1 C10 C11 C4 -0.4(2) . . . . ?
N9 C10 C11 C4 -179.16(12) . . . . ?
C1 C10 C11 C12 178.81(13) . . . . ?
N9 C10 C11 C12 0.06(15) . . . . ?
C6 C5 C12 C13 0.1(2) . . . . ?
C6 C5 C12 C11 179.71(17) . . . . ?
C4 C11 C12 C5 -0.8(3) . . . . ?
C10 C11 C12 C5 -179.87(16) . . . . ?
C4 C11 C12 C13 178.83(16) . . . . ?
C10 C11 C12 C13 -0.22(15) . . . . ?
C7 C8 C13 N9 179.90(14) . . . . ?
C7 C8 C13 C12 -0.2(2) . . . . ?
C10 N9 C13 C8 179.68(14) . . . . ?
C22 N9 C13 C8 0.8(2) . . . . ?
C10 N9 C13 C12 -0.26(15) . . . . ?
C22 N9 C13 C12 -179.17(12) . . . . ?
C5 C12 C13 C8 0.1(2) . . . . ?
C11 C12 C13 C8 -179.65(13) . . . . ?
C5 C12 C13 N9 -179.99(13) . . . . ?
C11 C12 C13 N9 0.29(15) . . . . ?
C25 C14 C15 C16 0.5(2) . . . . ?
C14 C15 C16 C17 -0.8(2) . . . . ?
C15 C16 C17 C24 0.4(2) . . . . ?
C27 C18 C19 C20 -0.4(3) . . . . ?
C18 C19 C20 C21 -0.3(3) . . . . ?
C19 C20 C21 C26 0.3(2) . . . . ?
C13 N9 C22 C26 -107.29(14) . . . . ?
C10 N9 C22 C26 73.98(17) . . . . ?
C13 N9 C22 C25 72.22(17) . . . . ?
C10 N9 C22 C25 -106.51(15) . . . . ?
C27 N23 C24 C17 179.91(13) . . . . ?
C27 N23 C24 C25 1.33(19) . . . . ?
C16 C17 C24 N23 -178.39(14) . . . . ?
C16 C17 C24 C25 0.2(2) . . . . ?
C26 C22 C25 C14 -179.35(12) . . . . ?
N9 C22 C25 C14 1.14(19) . . . . ?
C26 C22 C25 C24 -0.91(18) . . . . ?
N9 C22 C25 C24 179.58(10) . . . . ?
C15 C14 C25 C22 178.61(13) . . . . ?
C15 C14 C25 C24 0.2(2) . . . . ?
N23 C24 C25 C22 -0.47(18) . . . . ?
C17 C24 C25 C22 -179.06(12) . . . . ?
N23 C24 C25 C14 178.06(12) . . . . ?
C17 C24 C25 C14 -0.54(19) . . . . ?
C25 C22 C26 C21 -177.14(12) . . . . ?
N9 C22 C26 C21 2.36(19) . . . . ?
C25 C22 C26 C27 1.37(18) . . . . ?
N9 C22 C26 C27 -179.13(11) . . . . ?
C20 C21 C26 C22 178.76(14) . . . . ?
C20 C21 C26 C27 0.3(2) . . . . ?
C24 N23 C27 C18 178.19(12) . . . . ?
C24 N23 C27 C26 -0.84(19) . . . . ?
C19 C18 C27 N23 -178.04(15) . . . . ?
C19 C18 C27 C26 1.0(2) . . . . ?
C22 C26 C27 N23 -0.51(19) . . . . ?
C21 C26 C27 N23 178.09(12) . . . . ?
C22 C26 C27 C18 -179.53(12) . . . . ?
C21 C26 C27 C18 -0.93(19) . . . . ?
C36 C31 C32 F1 178.47(12) . . . . ?
C37 C31 C32 F1 -4.7(2) . . . . ?
C36 C31 C32 C33 -0.3(2) . . . . ?
C37 C31 C32 C33 176.49(13) . . . . ?
F1 C32 C33 F2 0.9(2) . . . . ?
C31 C32 C33 F2 179.73(13) . . . . ?
F1 C32 C33 C34 -178.93(13) . . . . ?
C31 C32 C33 C34 -0.1(2) . . . . ?
F2 C33 C34 F3 0.8(2) . . . . ?
C32 C33 C34 F3 -179.40(13) . . . . ?
F2 C33 C34 C35 -179.01(14) . . . . ?
C32 C33 C34 C35 0.8(2) . . . . ?
F3 C34 C35 F4 0.0(2) . . . . ?
C33 C34 C35 F4 179.77(14) . . . . ?
F3 C34 C35 C36 179.11(13) . . . . ?
C33 C34 C35 C36 -1.1(2) . . . . ?
F4 C35 C36 F5 2.4(2) . . . . ?
C34 C35 C36 F5 -176.77(14) . . . . ?
F4 C35 C36 C31 179.80(14) . . . . ?
C34 C35 C36 C31 0.7(2) . . . . ?
C32 C31 C36 F5 177.38(13) . . . . ?
C37 C31 C36 F5 0.7(2) . . . . ?
C32 C31 C36 C35 0.0(2) . . . . ?
C37 C31 C36 C35 -176.69(13) . . . . ?
C36 C31 C37 O2B -170(2) . . . . ?
C32 C31 C37 O2B 13(2) . . . . ?
C36 C31 C37 O2 140.4(2) . . . . ?
C32 C31 C37 O2 -36.2(3) . . . . ?
C36 C31 C37 O1B -4.9(12) . . . . ?
C32 C31 C37 O1B 178.5(12) . . . . ?
C36 C31 C37 O1 -36.1(3) . . . . ?
C32 C31 C37 O1 147.3(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
C18 H18 F4 0.93 2.43 3.1538(18) 134.6 1_545 yes
O1 H1A N23 0.89(2) 1.78(2) 2.653(2) 167(2) 2_656 yes

_refine_diff_density_max         0.202
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.031



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane/Dichloromethane'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_AC-THF_solvate-100K
_database_code_depnum_ccdc_archive 'CCDC 2351863'
loop_
_audit_author_name
_audit_author_address
'Ruben Alfredo Toscano'
;Institute of Chemistry, National Autonomous University of Mexico
Mexico
;
_audit_update_record             
;
2024-04-26 deposited with the CCDC.	2024-08-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H24 N2 O'
_chemical_formula_weight         416.50

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   14.1494(3)
_cell_length_b                   10.4352(2)
_cell_length_c                   15.0991(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.6880(10)
_cell_angle_gamma                90
_cell_volume                     2214.24(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9974
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      32.59

_exptl_crystal_description       prism
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.288
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_min          0.076
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6999
_exptl_absorpt_correction_T_max  0.7464
_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                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 83.333
_diffrn_reflns_number            32008
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.431
_diffrn_reflns_theta_max         32.592
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4042
_reflns_number_gt                3328
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX3 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    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.1029P)²+1.7658P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4042
_refine_ls_number_parameters     178
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0584
_refine_ls_wR_factor_ref         0.1870
_refine_ls_wR_factor_gt          0.1758
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_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
N1 N 0.500000 0.42813(11) 0.750000 0.0173(2) Uani 1 2 d S T P . .
N2 N 0.500000 0.83420(12) 0.750000 0.0194(3) Uani 1 2 d S T P . .
C1 C 0.48506(7) 0.35063(9) 0.67483(7) 0.0160(2) Uani 1 1 d . . . . .
C2 C 0.46502(9) 0.38730(10) 0.58584(7) 0.0199(2) Uani 1 1 d . . . . .
H2 H 0.461403 0.475031 0.568977 0.024 Uiso 1 1 calc R U . . .
C3 C 0.45058(9) 0.29013(11) 0.52292(8) 0.0231(2) Uani 1 1 d . . . . .
H3 H 0.436612 0.311769 0.461683 0.028 Uiso 1 1 calc R U . . .
C4 C 0.45620(9) 0.16053(11) 0.54796(8) 0.0230(2) Uani 1 1 d . . . . .
H4 H 0.446204 0.096123 0.503385 0.028 Uiso 1 1 calc R U . . .
C5 C 0.47615(8) 0.12488(10) 0.63692(7) 0.0195(2) Uani 1 1 d . . . . .
H5 H 0.480018 0.036993 0.653363 0.023 Uiso 1 1 calc R U . . .
C6 C 0.49040(7) 0.22083(9) 0.70164(7) 0.01558(19) Uani 1 1 d . . . . .
C7 C 0.57385(8) 0.76812(10) 0.72441(7) 0.0178(2) Uani 1 1 d . . . . .
C8 C 0.65235(9) 0.83841(12) 0.69694(8) 0.0251(2) Uani 1 1 d . . . . .
H8 H 0.651119 0.929427 0.697032 0.030 Uiso 1 1 calc R U . . .
C9 C 0.72868(9) 0.77574(14) 0.67070(9) 0.0299(3) Uani 1 1 d . . . . .
H9 H 0.780054 0.823551 0.652208 0.036 Uiso 1 1 calc R U . . .
C10 C 0.73257(9) 0.63921(14) 0.67059(9) 0.0285(3) Uani 1 1 d . . . . .
H10 H 0.786674 0.597107 0.652501 0.034 Uiso 1 1 calc R U . . .
C11 C 0.65940(8) 0.56843(11) 0.69620(8) 0.0219(2) Uani 1 1 d . . . . .
H11 H 0.662774 0.477512 0.695870 0.026 Uiso 1 1 calc R U . . .
C12 C 0.57774(7) 0.63073(10) 0.72350(7) 0.0161(2) Uani 1 1 d . . . . .
C13 C 0.500000 0.56428(13) 0.750000 0.0154(3) Uani 1 2 d S T P . .
O1 O 0.2736(11) 0.8399(10) 0.5158(6) 0.087(4) Uani 0.25 1 d . . P A -1
C14 C 0.2720(3) 0.7805(5) 0.4294(3) 0.0526(10) Uani 0.5 1 d . . P A -1
H14A H 0.229759 0.830722 0.385494 0.063 Uiso 0.5 1 calc R U P A -1
H14B H 0.336921 0.783364 0.411061 0.063 Uiso 0.5 1 calc R U P A -1
C15 C 0.2409(10) 0.6534(8) 0.4273(6) 0.121(4) Uani 0.5 1 d . . P A -1
H15A H 0.286753 0.596806 0.401558 0.146 Uiso 0.5 1 calc R U P A -1
H15B H 0.177943 0.645229 0.391498 0.146 Uiso 0.5 1 calc R U P A -1
C16 C 0.2345(5) 0.6199(8) 0.5230(6) 0.083(2) Uani 0.5 1 d . . P A -1
H16A H 0.169505 0.634847 0.539014 0.100 Uiso 0.5 1 calc R U P A -1
H16B H 0.252121 0.529223 0.535223 0.100 Uiso 0.5 1 calc R U P A -1
C17 C 0.2993(10) 0.7019(11) 0.5692(5) 0.158(6) Uani 0.5 1 d . . P A -1
H17A H 0.365616 0.674825 0.564565 0.190 Uiso 0.5 1 calc R U P A -1
H17B H 0.289236 0.707868 0.632837 0.190 Uiso 0.5 1 calc R U P A -1
O1A O 0.3048(7) 0.8144(9) 0.5517(7) 0.063(2) Uani 0.25 1 d . . 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
N1 C1 1.3896(12) 2_656 ?
N1 C1 1.3896(12) . ?
N1 C13 1.4207(18) . ?
N2 C7 1.3455(12) . ?
N2 C7 1.3455(13) 2_656 ?
C1 C2 1.3941(14) . ?
C1 C6 1.4132(14) . ?
C2 C3 1.3882(15) . ?
C2 H2 0.9500 . ?
C3 C4 1.4040(16) . ?
C3 H3 0.9500 . ?
C4 C5 1.3907(16) . ?
C4 H4 0.9500 . ?
C5 C6 1.3973(14) . ?
C5 H5 0.9500 . ?
C6 C6 1.454(2) 2_656 ?
C7 C8 1.4323(15) . ?
C7 C12 1.4350(15) . ?
C8 C9 1.3604(19) . ?
C8 H8 0.9500 . ?
C9 C10 1.426(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.3638(17) . ?
C10 H10 0.9500 . ?
C11 C12 1.4277(14) . ?
C11 H11 0.9500 . ?
C12 C13 1.3976(12) . ?
O1 C14 1.441(8) . ?
O1 C17 1.670(16) . ?
C14 C15 1.397(11) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.500(12) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.382(11) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?

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
C1 N1 C1 108.82(11) 2_656 . ?
C1 N1 C13 125.59(6) 2_656 . ?
C1 N1 C13 125.59(6) . . ?
C7 N2 C7 118.35(13) . 2_656 ?
N1 C1 C2 128.46(9) . . ?
N1 C1 C6 109.02(9) . . ?
C2 C1 C6 122.50(9) . . ?
C3 C2 C1 117.15(10) . . ?
C3 C2 H2 121.4 . . ?
C1 C2 H2 121.4 . . ?
C2 C3 C4 121.34(11) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 121.10(10) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 118.71(10) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C5 C6 C1 119.21(9) . . ?
C5 C6 C6 134.21(6) . 2_656 ?
C1 C6 C6 106.57(6) . 2_656 ?
N2 C7 C8 118.37(10) . . ?
N2 C7 C12 123.14(10) . . ?
C8 C7 C12 118.48(10) . . ?
C9 C8 C7 120.47(11) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 120.84(11) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C11 C10 C9 120.68(12) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 120.12(11) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C13 C12 C11 123.17(10) . . ?
C13 C12 C7 117.43(10) . . ?
C11 C12 C7 119.40(10) . . ?
C12 C13 C12 120.51(13) 2_656 . ?
C12 C13 N1 119.74(6) 2_656 . ?
C12 C13 N1 119.74(6) . . ?
C14 O1 C17 92.6(7) . . ?
C15 C14 O1 113.6(6) . . ?
C15 C14 H14A 108.8 . . ?
O1 C14 H14A 108.8 . . ?
C15 C14 H14B 108.8 . . ?
O1 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
C14 C15 C16 104.7(6) . . ?
C14 C15 H15A 110.8 . . ?
C16 C15 H15A 110.8 . . ?
C14 C15 H15B 110.8 . . ?
C16 C15 H15B 110.8 . . ?
H15A C15 H15B 108.9 . . ?
C17 C16 C15 103.3(7) . . ?
C17 C16 H16A 111.1 . . ?
C15 C16 H16A 111.1 . . ?
C17 C16 H16B 111.1 . . ?
C15 C16 H16B 111.1 . . ?
H16A C16 H16B 109.1 . . ?
C16 C17 O1 101.3(9) . . ?
C16 C17 H17A 111.5 . . ?
O1 C17 H17A 111.5 . . ?
C16 C17 H17B 111.5 . . ?
O1 C17 H17B 111.5 . . ?
H17A C17 H17B 109.3 . . ?

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
C1 N1 C1 C2 178.26(13) 2_656 . . . ?
C13 N1 C1 C2 -1.74(13) . . . . ?
C1 N1 C1 C6 0.00(5) 2_656 . . . ?
C13 N1 C1 C6 180.00(5) . . . . ?
N1 C1 C2 C3 -178.35(10) . . . . ?
C6 C1 C2 C3 -0.30(17) . . . . ?
C1 C2 C3 C4 -0.16(18) . . . . ?
C2 C3 C4 C5 0.2(2) . . . . ?
C3 C4 C5 C6 0.18(18) . . . . ?
C4 C5 C6 C1 -0.62(16) . . . . ?
C4 C5 C6 C6 178.14(14) . . . 2_656 ?
N1 C1 C6 C5 179.08(8) . . . . ?
C2 C1 C6 C5 0.70(16) . . . . ?
N1 C1 C6 C6 0.01(13) . . . 2_656 ?
C2 C1 C6 C6 -178.38(11) . . . 2_656 ?
C7 N2 C7 C8 179.83(11) 2_656 . . . ?
C7 N2 C7 C12 -0.28(7) 2_656 . . . ?
N2 C7 C8 C9 179.86(10) . . . . ?
C12 C7 C8 C9 -0.04(17) . . . . ?
C7 C8 C9 C10 -0.5(2) . . . . ?
C8 C9 C10 C11 0.5(2) . . . . ?
C9 C10 C11 C12 0.01(19) . . . . ?
C10 C11 C12 C13 179.58(10) . . . . ?
C10 C11 C12 C7 -0.52(16) . . . . ?
N2 C7 C12 C13 0.55(14) . . . . ?
C8 C7 C12 C13 -179.56(8) . . . . ?
N2 C7 C12 C11 -179.36(9) . . . . ?
C8 C7 C12 C11 0.53(15) . . . . ?
C11 C12 C13 C12 179.65(11) . . . 2_656 ?
C7 C12 C13 C12 -0.25(6) . . . 2_656 ?
C11 C12 C13 N1 -0.35(11) . . . . ?
C7 C12 C13 N1 179.75(6) . . . . ?
C1 N1 C13 C12 -74.90(7) 2_656 . . 2_656 ?
C1 N1 C13 C12 105.10(7) . . . 2_656 ?
C1 N1 C13 C12 105.10(7) 2_656 . . . ?
C1 N1 C13 C12 -74.90(7) . . . . ?
C17 O1 C14 C15 32.0(12) . . . . ?
O1 C14 C15 C16 -8.5(14) . . . . ?
C14 C15 C16 C17 -25.8(13) . . . . ?
C15 C16 C17 O1 44.7(11) . . . . ?
C14 O1 C17 C16 -46.8(10) . . . . ?

_refine_diff_density_max         0.575
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.067


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol/THF'
_chemical_properties_physical    Heat-sensitive
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_AC-TFTA_100K
_database_code_depnum_ccdc_archive 'CCDC 2351864'
loop_
_audit_author_name
_audit_author_address
'Ruben Alfredo Toscano'
;Institute of Chemistry, National Autonomous University of Mexico
Mexico
;
_audit_update_record             
;
2024-04-26 deposited with the CCDC.	2024-08-14 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         '2(C25 H16 N2), C8 H2 F4 O4'
_chemical_formula_sum            'C58 H34 F4 N4 O4'
_chemical_formula_weight         926.89

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

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

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

_cell_length_a                   8.2289(4)
_cell_length_b                   12.7093(7)
_cell_length_c                   20.3645(10)
_cell_angle_alpha                90.7200(10)
_cell_angle_beta                 95.6660(10)
_cell_angle_gamma                91.6730(10)
_cell_volume                     2118.23(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9894
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      32.66

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_F_000             956
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.386
_exptl_crystal_size_mid          0.214
_exptl_crystal_size_min          0.207
_exptl_absorpt_coefficient_mu    0.104
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6843
_exptl_absorpt_correction_T_max  0.7464
_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 APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 83.333
_diffrn_reflns_number            51935
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.010
_diffrn_reflns_theta_max         31.506
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             14071
_reflns_number_gt                11276
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX3 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)+(0.0598P)²+0.6927P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         14071
_refine_ls_number_parameters     637
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.1177
_refine_ls_wR_factor_gt          0.1088
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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
C1 C 0.81325(14) 0.62521(8) 0.30649(5) 0.0161(2) Uani 1 1 d . . . . .
H1 H 0.861988 0.677172 0.280928 0.019 Uiso 1 1 calc R U . . .
C2 C 0.74735(15) 0.65412(9) 0.36280(6) 0.0182(2) Uani 1 1 d . . . . .
H2 H 0.753695 0.725757 0.376962 0.022 Uiso 1 1 calc R U . . .
C3 C 0.66917(14) 0.57733(9) 0.40036(5) 0.0184(2) Uani 1 1 d . . . . .
H3 H 0.619964 0.598914 0.438408 0.022 Uiso 1 1 calc R U . . .
C4 C 0.66382(14) 0.47326(9) 0.38258(5) 0.0165(2) Uani 1 1 d . . . . .
H4 H 0.610880 0.423223 0.408168 0.020 Uiso 1 1 calc R U . . .
C5 C 0.82078(14) 0.19178(8) 0.24640(6) 0.0164(2) Uani 1 1 d . . . . .
H5 H 0.777924 0.143077 0.275731 0.020 Uiso 1 1 calc R U . . .
C6 C 0.89253(14) 0.15580(9) 0.19330(6) 0.0173(2) Uani 1 1 d . . . . .
H6 H 0.899352 0.082152 0.186014 0.021 Uiso 1 1 calc R U . . .
C7 C 0.95739(14) 0.22726(9) 0.14863(5) 0.0166(2) Uani 1 1 d . . . . .
H7 H 1.007117 0.200881 0.111872 0.020 Uiso 1 1 calc R U . . .
C8 C 0.94875(14) 0.33340(8) 0.15815(5) 0.01474(19) Uani 1 1 d . . . . .
H8 H 0.991351 0.380359 0.127738 0.018 Uiso 1 1 calc R U . . .
C9 C 0.87341(13) 0.48207(8) 0.22873(5) 0.01216(18) Uani 1 1 d . . . . .
N10 N 0.73902(11) 0.33546(7) 0.31146(4) 0.01380(17) Uani 1 1 d . . . . .
C11 C 0.80920(13) 0.51728(8) 0.28590(5) 0.01296(18) Uani 1 1 d . . . . .
C12 C 0.73761(13) 0.43934(8) 0.32560(5) 0.01301(18) Uani 1 1 d . . . . .
C13 C 0.80954(13) 0.30215(8) 0.25826(5) 0.01298(18) Uani 1 1 d . . . . .
C14 C 0.87599(13) 0.37416(8) 0.21360(5) 0.01258(18) Uani 1 1 d . . . . .
C15 C 0.73345(14) 0.55513(9) 0.08917(6) 0.0168(2) Uani 1 1 d . . . . .
H15 H 0.648117 0.524056 0.111279 0.020 Uiso 1 1 calc R U . . .
C16 C 0.70785(15) 0.58468(9) 0.02352(6) 0.0198(2) Uani 1 1 d . . . . .
H16 H 0.602526 0.573973 0.000392 0.024 Uiso 1 1 calc R U . . .
C17 C 0.83414(15) 0.62999(9) -0.00933(6) 0.0198(2) Uani 1 1 d . . . . .
H17 H 0.812558 0.650023 -0.054059 0.024 Uiso 1 1 calc R U . . .
C18 C 0.98970(14) 0.64591(9) 0.02251(5) 0.0171(2) Uani 1 1 d . . . . .
H18 H 1.075150 0.675525 -0.000174 0.021 Uiso 1 1 calc R U . . .
C19 C 1.32341(14) 0.65885(8) 0.13472(6) 0.0167(2) Uani 1 1 d . . . . .
H19 H 1.359649 0.685260 0.095060 0.020 Uiso 1 1 calc R U . . .
C20 C 1.43059(14) 0.65390(8) 0.19159(6) 0.0181(2) Uani 1 1 d . . . . .
H20 H 1.541059 0.677254 0.190695 0.022 Uiso 1 1 calc R U . . .
C21 C 1.37807(14) 0.61481(8) 0.25054(6) 0.0174(2) Uani 1 1 d . . . . .
H21 H 1.453790 0.612370 0.288808 0.021 Uiso 1 1 calc R U . . .
C22 C 1.21756(14) 0.57969(8) 0.25388(5) 0.01487(19) Uani 1 1 d . . . . .
H22 H 1.181854 0.553188 0.293609 0.018 Uiso 1 1 calc R U . . .
N23 N 0.94558(11) 0.55521(7) 0.18712(4) 0.01302(16) Uani 1 1 d . . . . .
C24 C 0.88964(13) 0.57306(8) 0.12109(5) 0.01320(18) Uani 1 1 d . . . . .
C25 C 1.01874(13) 0.61753(8) 0.08879(5) 0.01386(19) Uani 1 1 d . . . . .
C26 C 1.16112(13) 0.62427(8) 0.13684(5) 0.01398(19) Uani 1 1 d . . . . .
C27 C 1.11155(13) 0.58503(8) 0.19654(5) 0.01296(18) Uani 1 1 d . . . . .
F1 F 0.49895(9) 0.78769(5) 0.48369(4) 0.02057(15) Uani 1 1 d . . . . .
F2 F 0.66292(10) 0.90877(6) 0.40601(3) 0.02222(15) Uani 1 1 d . . . . .
O1 O 0.40918(11) 0.79110(7) 0.61230(4) 0.02102(17) Uani 1 1 d . . . . .
H1A H 0.349(2) 0.7485(14) 0.6391(9) 0.032 Uiso 1 1 d . U . . .
O2 O 0.18541(12) 0.88756(9) 0.59810(6) 0.0351(3) Uani 1 1 d . . . . .
C28 C 0.41537(13) 0.93549(8) 0.54216(5) 0.01407(19) Uani 1 1 d . . . . .
C29 C 0.50214(14) 0.89213(8) 0.49387(5) 0.01488(19) Uani 1 1 d . . . . .
C30 C 0.58548(14) 0.95551(8) 0.45295(5) 0.01481(19) Uani 1 1 d . . . . .
C31 C 0.32270(14) 0.86852(9) 0.58709(6) 0.0167(2) Uani 1 1 d . . . . .
C41 C 0.44321(14) 1.17314(8) 0.15879(5) 0.01498(19) Uani 1 1 d . . . . .
H41 H 0.485636 1.128111 0.127480 0.018 Uiso 1 1 calc R U . . .
C42 C 0.45133(14) 1.27955(9) 0.15107(5) 0.0166(2) Uani 1 1 d . . . . .
H42 H 0.500030 1.308176 0.114575 0.020 Uiso 1 1 calc R U . . .
C43 C 0.38735(15) 1.34794(9) 0.19730(6) 0.0178(2) Uani 1 1 d . . . . .
H43 H 0.393754 1.421902 0.191306 0.021 Uiso 1 1 calc R U . . .
C44 C 0.31689(14) 1.30875(8) 0.25016(6) 0.0163(2) Uani 1 1 d . . . . .
H44 H 0.274620 1.355514 0.280549 0.020 Uiso 1 1 calc R U . . .
C45 C 0.16269(13) 1.01965(9) 0.38155(5) 0.01485(19) Uani 1 1 d . . . . .
H45 H 0.116410 1.067962 0.409865 0.018 Uiso 1 1 calc R U . . .
C46 C 0.16067(14) 0.91475(9) 0.39507(5) 0.0165(2) Uani 1 1 d . . . . .
H46 H 0.112848 0.890679 0.432952 0.020 Uiso 1 1 calc R U . . .
C47 C 0.22924(14) 0.84052(9) 0.35323(5) 0.0167(2) Uani 1 1 d . . . . .
H47 H 0.228059 0.767984 0.363928 0.020 Uiso 1 1 calc R U . . .
C48 C 0.29658(14) 0.87309(8) 0.29787(5) 0.01490(19) Uani 1 1 d . . . . .
H48 H 0.340499 0.823026 0.269993 0.018 Uiso 1 1 calc R U . . .
C49 C 0.36655(13) 1.02053(8) 0.22579(5) 0.01229(18) Uani 1 1 d . . . . .
N50 N 0.23793(11) 1.16091(7) 0.31299(4) 0.01304(16) Uani 1 1 d . . . . .
C51 C 0.37151(13) 1.12908(8) 0.21353(5) 0.01244(18) Uani 1 1 d . . . . .
C52 C 0.30636(13) 1.19774(8) 0.26002(5) 0.01267(18) Uani 1 1 d . . . . .
C53 C 0.23452(13) 1.05672(8) 0.32475(5) 0.01259(18) Uani 1 1 d . . . . .
C54 C 0.30104(13) 0.98207(8) 0.28188(5) 0.01242(18) Uani 1 1 d . . . . .
C55 C 0.22584(14) 0.94932(9) 0.08335(6) 0.0174(2) Uani 1 1 d . . . . .
H55 H 0.142522 0.980414 0.105526 0.021 Uiso 1 1 calc R U . . .
C56 C 0.19947(15) 0.91901(10) 0.01722(6) 0.0200(2) Uani 1 1 d . . . . .
H56 H 0.095484 0.929001 -0.006157 0.024 Uiso 1 1 calc R U . . .
C57 C 0.32282(15) 0.87403(10) -0.01577(6) 0.0192(2) Uani 1 1 d . . . . .
H57 H 0.300868 0.854068 -0.060960 0.023 Uiso 1 1 calc R U . . .
C58 C 0.47615(14) 0.85828(9) 0.01653(5) 0.0159(2) Uani 1 1 d . . . . .
H58 H 0.559537 0.828348 -0.006161 0.019 Uiso 1 1 calc R U . . .
C59 C 0.80419(14) 0.84373(8) 0.12943(6) 0.01552(19) Uani 1 1 d . . . . .
H59 H 0.838183 0.816534 0.089494 0.019 Uiso 1 1 calc R U . . .
C60 C 0.91032(14) 0.84786(9) 0.18675(6) 0.0174(2) Uani 1 1 d . . . . .
H60 H 1.017953 0.823119 0.185977 0.021 Uiso 1 1 calc R U . . .
C61 C 0.86093(14) 0.88812(8) 0.24600(6) 0.0164(2) Uani 1 1 d . . . . .
H61 H 0.936259 0.890458 0.284508 0.020 Uiso 1 1 calc R U . . .
C62 C 0.70434(14) 0.92461(8) 0.24951(5) 0.01424(19) Uani 1 1 d . . . . .
H62 H 0.670786 0.951472 0.289607 0.017 Uiso 1 1 calc R U . . .
N63 N 0.43640(11) 0.95059(7) 0.18198(4) 0.01271(16) Uani 1 1 d . . . . .
C64 C 0.37992(13) 0.93208(8) 0.11571(5) 0.01295(18) Uani 1 1 d . . . . .
C65 C 0.50575(13) 0.88731(8) 0.08319(5) 0.01285(18) Uani 1 1 d . . . . .
C66 C 0.64608(13) 0.88038(8) 0.13152(5) 0.01249(18) Uani 1 1 d . . . . .
C67 C 0.59896(13) 0.92002(8) 0.19169(5) 0.01208(18) Uani 1 1 d . . . . .
F3 F 0.14425(10) 0.68717(5) 0.47357(4) 0.02424(16) Uani 1 1 d . . . . .
F4 F 0.24145(9) 0.51272(6) 0.41857(4) 0.02380(16) Uani 1 1 d . . . . .
O3 O -0.11591(11) 0.68883(7) 0.62199(4) 0.01986(17) Uani 1 1 d . . . . .
H3A H -0.159(2) 0.7536(14) 0.6427(8) 0.030 Uiso 1 1 d . U . . .
O4 O -0.14776(13) 0.76685(7) 0.52286(4) 0.0260(2) Uani 1 1 d . . . . .
C68 C -0.05088(14) 0.59326(8) 0.52976(5) 0.01465(19) Uani 1 1 d . . . . .
C69 C 0.06911(14) 0.59582(8) 0.48654(5) 0.0157(2) Uani 1 1 d . . . . .
C70 C 0.11867(14) 0.50467(9) 0.45752(5) 0.0156(2) Uani 1 1 d . . . . .
C71 C -0.11029(14) 0.69410(9) 0.55810(6) 0.0169(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
C1 C2 1.3666(15) . ?
C1 C11 1.4278(14) . ?
C1 H1 0.9500 . ?
C2 C3 1.4252(17) . ?
C2 H2 0.9500 . ?
C3 C4 1.3653(16) . ?
C3 H3 0.9500 . ?
C4 C12 1.4294(15) . ?
C4 H4 0.9500 . ?
C5 C6 1.3624(16) . ?
C5 C13 1.4276(14) . ?
C5 H5 0.9500 . ?
C6 C7 1.4233(16) . ?
C6 H6 0.9500 . ?
C7 C8 1.3653(15) . ?
C7 H7 0.9500 . ?
C8 C14 1.4279(14) . ?
C8 H8 0.9500 . ?
C9 C11 1.3990(14) . ?
C9 C14 1.4030(14) . ?
C9 N23 1.4220(13) . ?
N10 C13 1.3478(14) . ?
N10 C12 1.3483(13) . ?
C11 C12 1.4360(14) . ?
C13 C14 1.4331(14) . ?
C15 C16 1.3907(16) . ?
C15 C24 1.3931(15) . ?
C15 H15 0.9500 . ?
C16 C17 1.4041(17) . ?
C16 H16 0.9500 . ?
C17 C18 1.3848(17) . ?
C17 H17 0.9500 . ?
C18 C25 1.4009(15) . ?
C18 H18 0.9500 . ?
C19 C20 1.3879(17) . ?
C19 C26 1.3986(15) . ?
C19 H19 0.9500 . ?
C20 C21 1.4070(16) . ?
C20 H20 0.9500 . ?
C21 C22 1.3902(16) . ?
C21 H21 0.9500 . ?
C22 C27 1.3904(15) . ?
C22 H22 0.9500 . ?
N23 C27 1.4006(14) . ?
N23 C24 1.4009(13) . ?
C24 C25 1.4118(15) . ?
C25 C26 1.4503(15) . ?
C26 C27 1.4123(14) . ?
F1 C29 1.3400(12) . ?
F2 C30 1.3419(12) . ?
O1 C31 1.3113(14) . ?
O1 H1A 0.938(18) . ?
O2 C31 1.2041(15) . ?
C28 C30 1.3879(15) 2_676 ?
C28 C29 1.3887(15) . ?
C28 C31 1.5042(15) . ?
C29 C30 1.3825(15) . ?
C41 C42 1.3639(15) . ?
C41 C51 1.4249(15) . ?
C41 H41 0.9500 . ?
C42 C43 1.4223(15) . ?
C42 H42 0.9500 . ?
C43 C44 1.3649(16) . ?
C43 H43 0.9500 . ?
C44 C52 1.4289(15) . ?
C44 H44 0.9500 . ?
C45 C46 1.3648(15) . ?
C45 C53 1.4289(15) . ?
C45 H45 0.9500 . ?
C46 C47 1.4283(15) . ?
C46 H46 0.9500 . ?
C47 C48 1.3679(15) . ?
C47 H47 0.9500 . ?
C48 C54 1.4271(14) . ?
C48 H48 0.9500 . ?
C49 C54 1.3981(14) . ?
C49 C51 1.4052(14) . ?
C49 N63 1.4239(13) . ?
N50 C52 1.3479(14) . ?
N50 C53 1.3487(13) . ?
C51 C52 1.4325(14) . ?
C53 C54 1.4373(14) . ?
C55 C56 1.3905(16) . ?
C55 C64 1.3945(15) . ?
C55 H55 0.9500 . ?
C56 C57 1.4026(17) . ?
C56 H56 0.9500 . ?
C57 C58 1.3853(16) . ?
C57 H57 0.9500 . ?
C58 C65 1.3982(14) . ?
C58 H58 0.9500 . ?
C59 C60 1.3866(16) . ?
C59 C66 1.3990(15) . ?
C59 H59 0.9500 . ?
C60 C61 1.4058(16) . ?
C60 H60 0.9500 . ?
C61 C62 1.3902(16) . ?
C61 H61 0.9500 . ?
C62 C67 1.3912(15) . ?
C62 H62 0.9500 . ?
N63 C64 1.3982(13) . ?
N63 C67 1.3999(14) . ?
C64 C65 1.4124(14) . ?
C65 C66 1.4470(15) . ?
C66 C67 1.4125(14) . ?
F3 C69 1.3408(13) . ?
F4 C70 1.3471(13) . ?
O3 C71 1.3089(14) . ?
O3 H3A 1.010(17) . ?
O4 C71 1.2060(14) . ?
C68 C69 1.3860(15) . ?
C68 C70 1.3869(15) 2_566 ?
C68 C71 1.5127(15) . ?
C69 C70 1.3841(15) . ?

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 C11 120.33(10) . . ?
C2 C1 H1 119.8 . . ?
C11 C1 H1 119.8 . . ?
C1 C2 C3 120.32(10) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C2 121.09(10) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C12 120.21(10) . . ?
C3 C4 H4 119.9 . . ?
C12 C4 H4 119.9 . . ?
C6 C5 C13 120.47(10) . . ?
C6 C5 H5 119.8 . . ?
C13 C5 H5 119.8 . . ?
C5 C6 C7 120.77(10) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C8 C7 C6 120.58(10) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C14 120.31(10) . . ?
C7 C8 H8 119.8 . . ?
C14 C8 H8 119.8 . . ?
C11 C9 C14 120.69(9) . . ?
C11 C9 N23 120.15(9) . . ?
C14 C9 N23 119.06(9) . . ?
C13 N10 C12 119.62(9) . . ?
C9 C11 C1 123.44(10) . . ?
C9 C11 C12 117.30(9) . . ?
C1 C11 C12 119.25(9) . . ?
N10 C12 C4 118.90(9) . . ?
N10 C12 C11 122.42(9) . . ?
C4 C12 C11 118.67(9) . . ?
N10 C13 C5 119.16(9) . . ?
N10 C13 C14 122.04(9) . . ?
C5 C13 C14 118.79(9) . . ?
C9 C14 C8 123.11(9) . . ?
C9 C14 C13 117.73(9) . . ?
C8 C14 C13 119.08(9) . . ?
C16 C15 C24 117.12(10) . . ?
C16 C15 H15 121.4 . . ?
C24 C15 H15 121.4 . . ?
C15 C16 C17 121.49(11) . . ?
C15 C16 H16 119.3 . . ?
C17 C16 H16 119.3 . . ?
C18 C17 C16 120.96(11) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C17 C18 C25 118.77(10) . . ?
C17 C18 H18 120.6 . . ?
C25 C18 H18 120.6 . . ?
C20 C19 C26 118.83(10) . . ?
C20 C19 H19 120.6 . . ?
C26 C19 H19 120.6 . . ?
C19 C20 C21 120.99(11) . . ?
C19 C20 H20 119.5 . . ?
C21 C20 H20 119.5 . . ?
C22 C21 C20 121.30(11) . . ?
C22 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
C21 C22 C27 117.11(10) . . ?
C21 C22 H22 121.4 . . ?
C27 C22 H22 121.4 . . ?
C27 N23 C24 108.08(8) . . ?
C27 N23 C9 122.22(9) . . ?
C24 N23 C9 125.04(9) . . ?
C15 C24 N23 128.59(10) . . ?
C15 C24 C25 122.29(10) . . ?
N23 C24 C25 109.09(9) . . ?
C18 C25 C24 119.35(10) . . ?
C18 C25 C26 133.77(10) . . ?
C24 C25 C26 106.88(9) . . ?
C19 C26 C27 119.10(10) . . ?
C19 C26 C25 134.13(10) . . ?
C27 C26 C25 106.77(9) . . ?
C22 C27 N23 128.17(10) . . ?
C22 C27 C26 122.67(10) . . ?
N23 C27 C26 109.16(9) . . ?
C31 O1 H1A 111.8(11) . . ?
C30 C28 C29 117.34(10) 2_676 . ?
C30 C28 C31 120.47(10) 2_676 . ?
C29 C28 C31 122.18(10) . . ?
F1 C29 C30 118.61(9) . . ?
F1 C29 C28 120.27(10) . . ?
C30 C29 C28 121.01(10) . . ?
F2 C30 C29 118.06(9) . . ?
F2 C30 C28 120.25(9) . 2_676 ?
C29 C30 C28 121.64(10) . 2_676 ?
O2 C31 O1 125.72(11) . . ?
O2 C31 C28 121.88(10) . . ?
O1 C31 C28 112.39(10) . . ?
C42 C41 C51 120.42(10) . . ?
C42 C41 H41 119.8 . . ?
C51 C41 H41 119.8 . . ?
C41 C42 C43 120.44(10) . . ?
C41 C42 H42 119.8 . . ?
C43 C42 H42 119.8 . . ?
C44 C43 C42 120.89(10) . . ?
C44 C43 H43 119.6 . . ?
C42 C43 H43 119.6 . . ?
C43 C44 C52 120.33(10) . . ?
C43 C44 H44 119.8 . . ?
C52 C44 H44 119.8 . . ?
C46 C45 C53 119.90(10) . . ?
C46 C45 H45 120.1 . . ?
C53 C45 H45 120.1 . . ?
C45 C46 C47 121.13(10) . . ?
C45 C46 H46 119.4 . . ?
C47 C46 H46 119.4 . . ?
C48 C47 C46 120.51(10) . . ?
C48 C47 H47 119.7 . . ?
C46 C47 H47 119.7 . . ?
C47 C48 C54 120.17(10) . . ?
C47 C48 H48 119.9 . . ?
C54 C48 H48 119.9 . . ?
C54 C49 C51 120.55(9) . . ?
C54 C49 N63 120.32(9) . . ?
C51 C49 N63 119.06(9) . . ?
C52 N50 C53 119.95(9) . . ?
C49 C51 C41 123.00(9) . . ?
C49 C51 C52 117.69(9) . . ?
C41 C51 C52 119.27(9) . . ?
N50 C52 C44 119.28(9) . . ?
N50 C52 C51 122.07(9) . . ?
C44 C52 C51 118.64(10) . . ?
N50 C53 C45 118.93(9) . . ?
N50 C53 C54 121.93(9) . . ?
C45 C53 C54 119.15(9) . . ?
C49 C54 C48 123.11(9) . . ?
C49 C54 C53 117.75(9) . . ?
C48 C54 C53 119.14(9) . . ?
C56 C55 C64 117.08(10) . . ?
C56 C55 H55 121.5 . . ?
C64 C55 H55 121.5 . . ?
C55 C56 C57 121.54(11) . . ?
C55 C56 H56 119.2 . . ?
C57 C56 H56 119.2 . . ?
C58 C57 C56 121.01(10) . . ?
C58 C57 H57 119.5 . . ?
C56 C57 H57 119.5 . . ?
C57 C58 C65 118.68(10) . . ?
C57 C58 H58 120.7 . . ?
C65 C58 H58 120.7 . . ?
C60 C59 C66 118.73(10) . . ?
C60 C59 H59 120.6 . . ?
C66 C59 H59 120.6 . . ?
C59 C60 C61 120.95(10) . . ?
C59 C60 H60 119.5 . . ?
C61 C60 H60 119.5 . . ?
C62 C61 C60 121.49(10) . . ?
C62 C61 H61 119.3 . . ?
C60 C61 H61 119.3 . . ?
C61 C62 C67 117.02(10) . . ?
C61 C62 H62 121.5 . . ?
C67 C62 H62 121.5 . . ?
C64 N63 C67 108.22(8) . . ?
C64 N63 C49 125.49(9) . . ?
C67 N63 C49 122.93(9) . . ?
C55 C64 N63 128.88(10) . . ?
C55 C64 C65 122.13(10) . . ?
N63 C64 C65 108.97(9) . . ?
C58 C65 C64 119.55(10) . . ?
C58 C65 C66 133.46(10) . . ?
C64 C65 C66 106.98(9) . . ?
C59 C66 C67 119.31(10) . . ?
C59 C66 C65 133.93(10) . . ?
C67 C66 C65 106.75(9) . . ?
C62 C67 N63 128.44(9) . . ?
C62 C67 C66 122.49(10) . . ?
N63 C67 C66 109.06(9) . . ?
C71 O3 H3A 114.4(10) . . ?
C69 C68 C70 116.93(9) . 2_566 ?
C69 C68 C71 120.69(10) . . ?
C70 C68 C71 122.28(10) 2_566 . ?
F3 C69 C70 118.24(10) . . ?
F3 C69 C68 120.35(9) . . ?
C70 C69 C68 121.37(10) . . ?
F4 C70 C69 118.00(10) . . ?
F4 C70 C68 120.22(9) . 2_566 ?
C69 C70 C68 121.70(10) . 2_566 ?
O4 C71 O3 127.46(10) . . ?
O4 C71 C68 120.80(10) . . ?
O3 C71 C68 111.74(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 C1 C2 C3 -2.07(17) . . . . ?
C1 C2 C3 C4 2.56(18) . . . . ?
C2 C3 C4 C12 0.18(17) . . . . ?
C13 C5 C6 C7 -0.09(17) . . . . ?
C5 C6 C7 C8 -0.06(18) . . . . ?
C6 C7 C8 C14 0.71(17) . . . . ?
C14 C9 C11 C1 175.49(10) . . . . ?
N23 C9 C11 C1 -0.88(16) . . . . ?
C14 C9 C11 C12 -3.83(15) . . . . ?
N23 C9 C11 C12 179.80(9) . . . . ?
C2 C1 C11 C9 179.66(11) . . . . ?
C2 C1 C11 C12 -1.04(16) . . . . ?
C13 N10 C12 C4 -179.36(10) . . . . ?
C13 N10 C12 C11 -0.08(16) . . . . ?
C3 C4 C12 N10 176.07(10) . . . . ?
C3 C4 C12 C11 -3.24(16) . . . . ?
C9 C11 C12 N10 3.73(16) . . . . ?
C1 C11 C12 N10 -175.62(10) . . . . ?
C9 C11 C12 C4 -176.99(10) . . . . ?
C1 C11 C12 C4 3.66(15) . . . . ?
C12 N10 C13 C5 175.55(10) . . . . ?
C12 N10 C13 C14 -3.51(16) . . . . ?
C6 C5 C13 N10 -179.50(10) . . . . ?
C6 C5 C13 C14 -0.41(16) . . . . ?
C11 C9 C14 C8 -176.11(10) . . . . ?
N23 C9 C14 C8 0.30(16) . . . . ?
C11 C9 C14 C13 0.56(15) . . . . ?
N23 C9 C14 C13 176.97(9) . . . . ?
C7 C8 C14 C9 175.44(10) . . . . ?
C7 C8 C14 C13 -1.19(16) . . . . ?
N10 C13 C14 C9 3.28(16) . . . . ?
C5 C13 C14 C9 -175.78(10) . . . . ?
N10 C13 C14 C8 -179.91(10) . . . . ?
C5 C13 C14 C8 1.03(15) . . . . ?
C24 C15 C16 C17 0.42(17) . . . . ?
C15 C16 C17 C18 0.64(18) . . . . ?
C16 C17 C18 C25 -1.05(17) . . . . ?
C26 C19 C20 C21 0.07(16) . . . . ?
C19 C20 C21 C22 0.12(16) . . . . ?
C20 C21 C22 C27 -0.07(15) . . . . ?
C11 C9 N23 C27 88.78(13) . . . . ?
C14 C9 N23 C27 -87.65(12) . . . . ?
C11 C9 N23 C24 -118.35(12) . . . . ?
C14 C9 N23 C24 65.22(14) . . . . ?
C16 C15 C24 N23 176.91(10) . . . . ?
C16 C15 C24 C25 -1.07(16) . . . . ?
C27 N23 C24 C15 179.93(10) . . . . ?
C9 N23 C24 C15 23.87(17) . . . . ?
C27 N23 C24 C25 -1.87(11) . . . . ?
C9 N23 C24 C25 -157.93(10) . . . . ?
C17 C18 C25 C24 0.41(16) . . . . ?
C17 C18 C25 C26 -178.72(11) . . . . ?
C15 C24 C25 C18 0.67(16) . . . . ?
N23 C24 C25 C18 -177.66(9) . . . . ?
C15 C24 C25 C26 -179.98(10) . . . . ?
N23 C24 C25 C26 1.69(11) . . . . ?
C20 C19 C26 C27 -0.29(15) . . . . ?
C20 C19 C26 C25 -179.86(11) . . . . ?
C18 C25 C26 C19 -2.0(2) . . . . ?
C24 C25 C26 C19 178.75(11) . . . . ?
C18 C25 C26 C27 178.34(11) . . . . ?
C24 C25 C26 C27 -0.86(11) . . . . ?
C21 C22 C27 N23 -179.80(10) . . . . ?
C21 C22 C27 C26 -0.16(15) . . . . ?
C24 N23 C27 C22 -179.00(10) . . . . ?
C9 N23 C27 C22 -22.13(16) . . . . ?
C24 N23 C27 C26 1.32(11) . . . . ?
C9 N23 C27 C26 158.19(9) . . . . ?
C19 C26 C27 C22 0.34(15) . . . . ?
C25 C26 C27 C22 -179.97(9) . . . . ?
C19 C26 C27 N23 -179.96(9) . . . . ?
C25 C26 C27 N23 -0.27(11) . . . . ?
C30 C28 C29 F1 -175.58(10) 2_676 . . . ?
C31 C28 C29 F1 3.35(16) . . . . ?
C30 C28 C29 C30 0.67(18) 2_676 . . . ?
C31 C28 C29 C30 179.59(10) . . . . ?
F1 C29 C30 F2 -1.75(16) . . . . ?
C28 C29 C30 F2 -178.06(10) . . . . ?
F1 C29 C30 C28 175.62(10) . . . 2_676 ?
C28 C29 C30 C28 -0.69(19) . . . 2_676 ?
C30 C28 C31 O2 44.92(17) 2_676 . . . ?
C29 C28 C31 O2 -133.97(14) . . . . ?
C30 C28 C31 O1 -134.06(11) 2_676 . . . ?
C29 C28 C31 O1 47.05(15) . . . . ?
C51 C41 C42 C43 -0.42(17) . . . . ?
C41 C42 C43 C44 0.04(18) . . . . ?
C42 C43 C44 C52 0.08(17) . . . . ?
C53 C45 C46 C47 -0.09(17) . . . . ?
C45 C46 C47 C48 -0.98(17) . . . . ?
C46 C47 C48 C54 0.90(17) . . . . ?
C54 C49 C51 C41 177.17(10) . . . . ?
N63 C49 C51 C41 0.20(16) . . . . ?
C54 C49 C51 C52 -0.46(15) . . . . ?
N63 C49 C51 C52 -177.43(9) . . . . ?
C42 C41 C51 C49 -176.92(11) . . . . ?
C42 C41 C51 C52 0.67(16) . . . . ?
C53 N50 C52 C44 -176.67(10) . . . . ?
C53 N50 C52 C51 2.37(15) . . . . ?
C43 C44 C52 N50 179.25(10) . . . . ?
C43 C44 C52 C51 0.18(16) . . . . ?
C49 C51 C52 N50 -1.87(15) . . . . ?
C41 C51 C52 N50 -179.59(10) . . . . ?
C49 C51 C52 C44 177.18(10) . . . . ?
C41 C51 C52 C44 -0.54(15) . . . . ?
C52 N50 C53 C45 179.42(10) . . . . ?
C52 N50 C53 C54 -0.55(15) . . . . ?
C46 C45 C53 N50 -178.78(10) . . . . ?
C46 C45 C53 C54 1.19(16) . . . . ?
C51 C49 C54 C48 -178.30(10) . . . . ?
N63 C49 C54 C48 -1.36(16) . . . . ?
C51 C49 C54 C53 2.12(15) . . . . ?
N63 C49 C54 C53 179.06(9) . . . . ?
C47 C48 C54 C49 -179.36(11) . . . . ?
C47 C48 C54 C53 0.21(16) . . . . ?
N50 C53 C54 C49 -1.69(15) . . . . ?
C45 C53 C54 C49 178.34(10) . . . . ?
N50 C53 C54 C48 178.72(10) . . . . ?
C45 C53 C54 C48 -1.25(15) . . . . ?
C64 C55 C56 C57 -0.63(18) . . . . ?
C55 C56 C57 C58 -0.09(19) . . . . ?
C56 C57 C58 C65 0.55(17) . . . . ?
C66 C59 C60 C61 -0.08(16) . . . . ?
C59 C60 C61 C62 0.38(17) . . . . ?
C60 C61 C62 C67 -0.34(16) . . . . ?
C54 C49 N63 C64 117.66(12) . . . . ?
C51 C49 N63 C64 -65.35(14) . . . . ?
C54 C49 N63 C67 -85.50(13) . . . . ?
C51 C49 N63 C67 91.48(12) . . . . ?
C56 C55 C64 N63 -176.96(11) . . . . ?
C56 C55 C64 C65 0.91(17) . . . . ?
C67 N63 C64 C55 179.37(11) . . . . ?
C49 N63 C64 C55 -20.97(17) . . . . ?
C67 N63 C64 C65 1.28(11) . . . . ?
C49 N63 C64 C65 160.94(10) . . . . ?
C57 C58 C65 C64 -0.28(16) . . . . ?
C57 C58 C65 C66 178.44(11) . . . . ?
C55 C64 C65 C58 -0.47(16) . . . . ?
N63 C64 C65 C58 177.78(9) . . . . ?
C55 C64 C65 C66 -179.50(10) . . . . ?
N63 C64 C65 C66 -1.25(11) . . . . ?
C60 C59 C66 C67 -0.22(15) . . . . ?
C60 C59 C66 C65 -179.34(11) . . . . ?
C58 C65 C66 C59 1.1(2) . . . . ?
C64 C65 C66 C59 179.94(11) . . . . ?
C58 C65 C66 C67 -178.09(11) . . . . ?
C64 C65 C66 C67 0.74(11) . . . . ?
C61 C62 C67 N63 179.50(10) . . . . ?
C61 C62 C67 C66 0.02(15) . . . . ?
C64 N63 C67 C62 179.66(10) . . . . ?
C49 N63 C67 C62 19.37(16) . . . . ?
C64 N63 C67 C66 -0.80(11) . . . . ?
C49 N63 C67 C66 -161.09(9) . . . . ?
C59 C66 C67 C62 0.26(15) . . . . ?
C65 C66 C67 C62 179.59(9) . . . . ?
C59 C66 C67 N63 -179.30(9) . . . . ?
C65 C66 C67 N63 0.03(11) . . . . ?
C70 C68 C69 F3 -177.72(10) 2_566 . . . ?
C71 C68 C69 F3 5.71(16) . . . . ?
C70 C68 C69 C70 -0.01(18) 2_566 . . . ?
C71 C68 C69 C70 -176.58(10) . . . . ?
F3 C69 C70 F4 0.94(16) . . . . ?
C68 C69 C70 F4 -176.82(10) . . . . ?
F3 C69 C70 C68 177.77(10) . . . 2_566 ?
C68 C69 C70 C68 0.01(19) . . . 2_566 ?
C69 C68 C71 O4 48.30(17) . . . . ?
C70 C68 C71 O4 -128.08(13) 2_566 . . . ?
C69 C68 C71 O3 -132.56(11) . . . . ?
C70 C68 C71 O3 51.06(15) 2_566 . . . ?

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
C5 H5 O2 0.95 2.59 3.3402(15) 135.8 2_666 yes
C22 H22 F4 0.95 2.60 3.4587(13) 149.8 1_655 yes
O1 H1A N10 0.938(18) 1.675(18) 2.6089(12) 173.6(17) 2_666 yes
C44 H44 O3 0.95 2.54 3.2197(14) 128.5 2_576 yes
C45 H45 O2 0.95 2.55 3.1917(14) 124.8 2_576 yes
C45 H45 O4 0.95 2.49 3.3318(14) 148.4 2_576 yes
C62 H62 F2 0.95 2.45 3.2466(13) 142.0 . yes
O3 H3A N50 1.010(17) 1.595(18) 2.5923(11) 168.0(16) 2_576 yes

_refine_diff_density_max         0.537
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.056


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol/Dichloromethane'
_exptl_crystal_preparation       Luminescent
