# Supplementary Information (SI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_yjs-gq-183
_audit_block_doi                 10.5517/ccdc.csd.cc278khl
_database_code_depnum_ccdc_archive 'CCDC 2063809'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D1CC01533H 2021
loop_
_audit_author_name
_audit_author_address
'Jie Li'
;Chengdu University of Information Technology
China
;
_audit_update_record             
;
2021-02-19 deposited with the CCDC.	2024-12-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C39 H29 F N6'
_chemical_formula_weight         600.68

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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           167
_space_group_name_H-M_alt        'R -3 c :H'
_space_group_name_Hall           '-R 3 2"c'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z+1/2'
'x-y, -y, -z+1/2'
'-x, -x+y, -z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'y+2/3, x+1/3, -z+5/6'
'x-y+2/3, -y+1/3, -z+5/6'
'-x+2/3, -x+y+1/3, -z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'y+1/3, x+2/3, -z+7/6'
'x-y+1/3, -y+2/3, -z+7/6'
'-x+1/3, -x+y+2/3, -z+7/6'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-y, -x, z-1/2'
'-x+y, y, z-1/2'
'x, x-y, z-1/2'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-y+2/3, -x+1/3, z-1/6'
'-x+y+2/3, y+1/3, z-1/6'
'x+2/3, x-y+1/3, z-1/6'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
'-y+1/3, -x+2/3, z+1/6'
'-x+y+1/3, y+2/3, z+1/6'
'x+1/3, x-y+2/3, z+1/6'

_cell_length_a                   14.5389(9)
_cell_length_b                   14.5389(9)
_cell_length_c                   25.5523(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     4677.6(6)
_cell_formula_units_Z            6
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2518
_cell_measurement_theta_min      3.895
_cell_measurement_theta_max      71.698

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_F_000             1884
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.649
_shelx_estimated_absorpt_T_min   0.870
_shelx_estimated_absorpt_T_max   0.892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5217
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         4.931
_diffrn_reflns_theta_max         71.660
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1011
_reflns_number_gt                937
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0738P)²+2.5495P] 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         1011
_refine_ls_number_parameters     79
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1334
_refine_ls_wR_factor_gt          0.1297
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.121
_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 0.6667 0.42216(11) 0.5833 0.0382(4) Uani 1 2 d S T P . .
C2 C 0.76297(10) 0.61635(10) 0.57626(5) 0.0412(4) Uani 1 1 d . . . . .
C3 C 0.82498(12) 0.63541(11) 0.53203(6) 0.0525(4) Uani 1 1 d . . . . .
H3 H 0.8048 0.5831 0.5065 0.063 Uiso 1 1 calc R U . . .
C4 C 0.91685(12) 0.73215(13) 0.52580(8) 0.0615(5) Uani 1 1 d . . . . .
H4 H 0.9589 0.7447 0.4963 0.074 Uiso 1 1 calc R U . . .
C5 C 0.94606(13) 0.80970(13) 0.56316(9) 0.0666(5) Uani 1 1 d D . . . .
H5 H 1.0084 0.8744 0.5591 0.080 Uiso 0.8333 1 calc R U P A 1
F1 F 1.0265(5) 0.9002(5) 0.5651(4) 0.111(3) Uani 0.1667 1 d D . P B 2
C6 C 0.88340(14) 0.79204(12) 0.60650(7) 0.0644(5) Uani 1 1 d . . . . .
H6 H 0.9027 0.8453 0.6314 0.077 Uiso 1 1 calc R U . . .
C7 C 0.79155(12) 0.69504(12) 0.61323(6) 0.0510(4) Uani 1 1 d . . . . .
H7 H 0.7493 0.6831 0.6426 0.061 Uiso 1 1 calc R U . . .
N1 N 0.57197(9) 0.3333 0.5833 0.0421(4) Uani 1 2 d S T P . .
N2 N 0.6667 0.51685(10) 0.5833 0.0434(4) Uani 1 2 d S T P . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0333(8) 0.0310(7) 0.0510(10) 0.0013(3) 0.0027(7) 0.0167(4)
C2 0.0327(7) 0.0303(6) 0.0620(8) 0.0044(5) 0.0027(5) 0.0167(5)
C3 0.0450(8) 0.0387(7) 0.0722(9) 0.0018(6) 0.0135(7) 0.0198(6)
C4 0.0454(8) 0.0484(9) 0.0881(12) 0.0140(8) 0.0211(8) 0.0215(7)
C5 0.0404(8) 0.0381(8) 0.1078(14) 0.0056(8) 0.0017(8) 0.0095(6)
F1 0.053(4) 0.051(4) 0.167(8) -0.001(4) 0.032(4) -0.020(3)
C6 0.0538(9) 0.0435(8) 0.0846(11) -0.0123(7) -0.0100(8) 0.0159(7)
C7 0.0469(8) 0.0430(8) 0.0608(9) -0.0010(6) -0.0001(6) 0.0206(6)
N1 0.0307(6) 0.0304(7) 0.0650(10) 0.0026(6) 0.0013(3) 0.0152(4)
N2 0.0316(8) 0.0295(6) 0.0697(10) 0.0039(3) 0.0078(7) 0.0158(4)

_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 N1 1.3361(10) . ?
C1 N1 1.3361(10) 3_665 ?
C1 N2 1.377(2) . ?
C2 C7 1.378(2) . ?
C2 C3 1.385(2) . ?
C2 N2 1.4353(14) . ?
C3 C4 1.382(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(3) . ?
C4 H4 0.9300 . ?
C5 F1 1.250(6) . ?
C5 C6 1.374(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.385(2) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
N1 C1 1.3361(10) 2_655 ?
N2 C2 1.4353(14) 18_655 ?

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
N1 C1 N1 126.34(16) . 3_665 ?
N1 C1 N2 116.83(8) . . ?
N1 C1 N2 116.83(8) 3_665 . ?
C7 C2 C3 119.84(13) . . ?
C7 C2 N2 119.20(12) . . ?
C3 C2 N2 120.92(11) . . ?
C4 C3 C2 119.95(14) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C5 C4 C3 120.04(16) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
F1 C5 C4 129.4(5) . . ?
F1 C5 C6 110.4(5) . . ?
C4 C5 C6 120.20(15) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C7 120.13(16) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C2 C7 C6 119.82(15) . . ?
C2 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C1 N1 C1 113.66(16) . 2_655 ?
C1 N2 C2 121.34(7) . 18_655 ?
C1 N2 C2 121.34(7) . . ?
C2 N2 C2 117.32(13) 18_655 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 C2 C3 C4 1.8(2) . . . . ?
N2 C2 C3 C4 179.38(13) . . . . ?
C2 C3 C4 C5 -0.7(2) . . . . ?
C3 C4 C5 F1 178.1(7) . . . . ?
C3 C4 C5 C6 -0.9(3) . . . . ?
F1 C5 C6 C7 -177.9(6) . . . . ?
C4 C5 C6 C7 1.3(3) . . . . ?
C3 C2 C7 C6 -1.4(2) . . . . ?
N2 C2 C7 C6 -178.99(13) . . . . ?
C5 C6 C7 C2 -0.2(2) . . . . ?
N1 C1 N1 C1 0.000(0) 3_665 . . 2_655 ?
N2 C1 N1 C1 180.003(1) . . . 2_655 ?
N1 C1 N2 C2 8.47(6) . . . 18_655 ?
N1 C1 N2 C2 -171.53(6) 3_665 . . 18_655 ?
N1 C1 N2 C2 -171.53(6) . . . . ?
N1 C1 N2 C2 8.48(6) 3_665 . . . ?
C7 C2 N2 C1 -124.83(10) . . . . ?
C3 C2 N2 C1 57.59(14) . . . . ?
C7 C2 N2 C2 55.17(10) . . . 18_655 ?
C3 C2 N2 C2 -122.41(14) . . . 18_655 ?

_refine_diff_density_max         0.146
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.037

_shelx_res_file                  
;

    yjs-gq-183.res created by SHELXL-2014/7

TITL yjs-gq-183_a.res in R-3c
CELL 1.54184 14.538859 14.538859 25.552313 90 90 120
ZERR 6 0.00087 0.00087 0.001607 0 0 0
LATT 3
SYMM -Y,+X-Y,+Z
SYMM +Y-X,-X,+Z
SYMM +Y,+X,0.5-Z
SYMM -Y+X,-Y,0.5-Z
SYMM -X,-X+Y,0.5-Z
SFAC C  H  N  F
UNIT 234 174 36 6
L.S. 20
SIZE 0.22 0.2 0.18
CONF
ACTA
BOND $H
FMAP 2
PLAN 20
LIST 6
dfix 1.38 0.02 c5 f1
WGHT    0.073800    2.549500
FVAR       0.19474
C1    1    0.666667    0.422156    0.583333    10.50000    0.03332    0.03101 =
         0.05101    0.00134    0.00269    0.01666
C2    1    0.762966    0.616350    0.576264    11.00000    0.03267    0.03030 =
         0.06198    0.00442    0.00268    0.01668
C3    1    0.824982    0.635414    0.532034    11.00000    0.04504    0.03871 =
         0.07224    0.00184    0.01347    0.01978
AFIX  43
H3    2    0.804814    0.583144    0.506544    11.00000   -1.20000
AFIX   0
C4    1    0.916847    0.732148    0.525800    11.00000    0.04545    0.04836 =
         0.08814    0.01398    0.02112    0.02155
AFIX  43
H4    2    0.958917    0.744729    0.496274    11.00000   -1.20000
AFIX   0
C5    1    0.946059    0.809703    0.563165    11.00000    0.04037    0.03814 =
         0.10785    0.00556    0.00167    0.00952
PART 1
AFIX  43
H5    2    1.008449    0.874397    0.559135    10.83333   -1.20000
PART 2
AFIX   0
F1    4    1.026493    0.900172    0.565119    10.16667    0.05323    0.05073 =
         0.16696   -0.00075    0.03152   -0.01954
PART 0
C6    1    0.883403    0.792041    0.606501    11.00000    0.05380    0.04346 =
         0.08455   -0.01234   -0.00998    0.01586
AFIX  43
H6    2    0.902706    0.845318    0.631362    11.00000   -1.20000
AFIX   0
C7    1    0.791547    0.695038    0.613228    11.00000    0.04689    0.04297 =
         0.06081   -0.00102   -0.00013    0.02061
AFIX  43
H7    2    0.749278    0.683056    0.642617    11.00000   -1.20000
AFIX   0
N1    3    0.571975    0.333333    0.583333    10.50000    0.03071    0.03037 =
         0.06498    0.00263    0.00132    0.01518
N2    3    0.666667    0.516853    0.583333    10.50000    0.03164    0.02947 =
         0.06968    0.00389    0.00777    0.01582
HKLF 4

REM  yjs-gq-183_a.res in R-3c
REM R1 =  0.0462 for     937 Fo > 4sig(Fo)  and  0.0489 for all    1011 data
REM     79 parameters refined using      1 restraints

END

WGHT      0.0731      2.5510

REM Highest difference peak  0.146,  deepest hole -0.183,  1-sigma level  0.037
Q1    1   0.9007  0.8505  0.6545  11.00000  0.05    0.15
Q2    1   0.8296  0.5635  0.5225  11.00000  0.05    0.15
Q3    1   0.5014  0.3333  0.5833  10.50000  0.05    0.14
Q4    1   0.9465  0.7199  0.5522  11.00000  0.05    0.13
Q5    1   0.8234  0.6127  0.5656  11.00000  0.05    0.13
Q6    1   0.7679  0.6582  0.6564  11.00000  0.05    0.12
Q7    1   0.9241  0.6868  0.5444  11.00000  0.05    0.10
Q8    1   0.7126  0.6887  0.6315  11.00000  0.05    0.10
Q9    1   0.6228  0.3578  0.5445  11.00000  0.05    0.10
Q10   1   0.8006  0.6393  0.6108  11.00000  0.05    0.09
Q11   1   0.9962  0.7341  0.5105  11.00000  0.05    0.09
Q12   1   0.7551  0.6731  0.5838  11.00000  0.05    0.09
Q13   1   0.7845  0.5828  0.4902  11.00000  0.05    0.09
Q14   1   0.8997  0.7764  0.5365  11.00000  0.05    0.09
Q15   1   0.9355  0.7383  0.4688  11.00000  0.05    0.09
Q16   1   0.8539  0.6911  0.5231  11.00000  0.05    0.08
Q17   1   0.6552  0.4744  0.5537  11.00000  0.05    0.08
Q18   1   0.9360  0.8936  0.6723  11.00000  0.05    0.08
Q19   1   0.8777  0.7368  0.6208  11.00000  0.05    0.08
Q20   1   0.7743  0.6342  0.5462  11.00000  0.05    0.08
;
_shelx_res_checksum              88002
####################################################################### 
# 
# 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_22_a
_database_code_depnum_ccdc_archive 'CCDC 2392813'
loop_
_audit_author_name
_audit_author_address
'Qiang Guo'
;Chengdu University of Information and Technology
China
;
_audit_update_record             
;
2024-11-27 deposited with the CCDC.	2024-12-09 downloaded from the CCDC.
;
_audit_creation_date             2022-11-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6396)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C39 H29 F1 N6'
_chemical_formula_sum            'C39 H29 F N6'
_chemical_formula_weight         600.68
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      trigonal
_space_group_IT_number           167
_space_group_name_H-M_alt        'R -3 c'
_space_group_name_Hall           '-R 3 2"c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z+1/2'
'x-y, -y, -z+1/2'
'-x, -x+y, -z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'y+2/3, x+1/3, -z+5/6'
'x-y+2/3, -y+1/3, -z+5/6'
'-x+2/3, -x+y+1/3, -z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'y+1/3, x+2/3, -z+7/6'
'x-y+1/3, -y+2/3, -z+7/6'
'-x+1/3, -x+y+2/3, -z+7/6'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-y, -x, z-1/2'
'-x+y, y, z-1/2'
'x, x-y, z-1/2'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-y+2/3, -x+1/3, z-1/6'
'-x+y+2/3, y+1/3, z-1/6'
'x+2/3, x-y+1/3, z-1/6'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
'-y+1/3, -x+2/3, z+1/6'
'-x+y+1/3, y+2/3, z+1/6'
'x+1/3, x-y+2/3, z+1/6'

_cell_length_a                   14.3814(4)
_cell_length_b                   14.3814(4)
_cell_length_c                   25.5525(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     4576.8(3)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    2196
_cell_measurement_temperature    298.00
_cell_measurement_theta_max      26.639
_cell_measurement_theta_min      2.284
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6535
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1454 before and 0.0669 after correction.
The Ratio of minimum to maximum transmission is 0.8765.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1884
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0591
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            9328
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.490
_diffrn_reflns_theta_min         2.833
_diffrn_ambient_temperature      298.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                839
_reflns_number_total             1173
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         1173
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0417
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0611P)²+1.4054P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1000
_refine_ls_wR_factor_ref         0.1136
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All F(H) groups
2. Restrained distances
 C6-H6
 0.94 with sigma of 0.001
3. Others
 Fixed Sof: F1(0.16667) H6(0.83333)
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C7(H7)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.333333 0.57072(10) 0.416667 0.0302(4) Uani 1 2 d S T P . .
N2 N 0.51896(10) 0.666667 0.416667 0.0307(4) Uani 1 2 d S T P . .
C1 C 0.42301(12) 0.666667 0.416667 0.0269(4) Uani 1 2 d S T P . .
C2 C 0.52183(9) 0.56923(10) 0.40903(5) 0.0285(3) Uani 1 1 d . . . . .
C3 C 0.47800(11) 0.50743(11) 0.36452(6) 0.0359(4) Uani 1 1 d . . . . .
H3 H 0.445609 0.528931 0.338948 0.043 Uiso 1 1 calc R U . . .
C4 C 0.48198(11) 0.41423(11) 0.35779(6) 0.0406(4) Uani 1 1 d . . . . .
H4 H 0.451770 0.372163 0.327689 0.049 Uiso 1 1 calc R U . . .
C5 C 0.53006(12) 0.38235(11) 0.39499(7) 0.0436(4) Uani 1 1 d . . . . .
H5 H 0.531916 0.318414 0.390546 0.052 Uiso 1 1 calc R U . . .
C6 C 0.57528(12) 0.44526(12) 0.43870(6) 0.0414(4) Uani 1 1 d D . . . .
C7 C 0.57117(11) 0.53877(11) 0.44613(6) 0.0334(4) Uani 1 1 d . . . . .
H7 H 0.601722 0.580961 0.476163 0.040 Uiso 1 1 calc R U . . .
F1 F 0.6147(7) 0.4074(6) 0.4686(3) 0.0529(15) Uani 0.1667 1 d . . P A 1
H6 H 0.608(2) 0.423(2) 0.4636(11) 0.063 Uiso 0.8333 1 d D U P B 2

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0206(7) 0.0211(6) 0.0487(10) -0.0005(3) -0.0011(6) 0.0103(4)
N2 0.0193(6) 0.0200(8) 0.0531(10) -0.0041(7) -0.0021(3) 0.0100(4)
C1 0.0214(7) 0.0226(9) 0.0371(10) -0.0012(7) -0.0006(4) 0.0113(4)
C2 0.0195(6) 0.0215(6) 0.0448(8) 0.0002(5) 0.0031(5) 0.0105(5)
C3 0.0290(7) 0.0310(7) 0.0496(8) -0.0060(6) -0.0061(6) 0.0163(6)
C4 0.0319(8) 0.0308(8) 0.0580(9) -0.0127(7) -0.0037(7) 0.0149(7)
C5 0.0381(8) 0.0257(7) 0.0712(11) -0.0017(7) 0.0034(8) 0.0192(7)
C6 0.0393(8) 0.0326(8) 0.0572(10) 0.0070(7) 0.0019(7) 0.0215(7)
C7 0.0294(7) 0.0298(7) 0.0414(8) -0.0001(6) 0.0016(6) 0.0151(6)
F1 0.071(4) 0.048(3) 0.054(3) 0.002(3) -0.017(3) 0.040(3)

_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 1.3370(11) 3_565 ?
N1 C1 1.3371(11) . ?
N2 C1 1.380(2) . ?
N2 C2 1.4357(14) . ?
N2 C2 1.4357(14) 11_565 ?
C2 C3 1.3859(19) . ?
C2 C7 1.3802(19) . ?
C3 H3 0.9400 . ?
C3 C4 1.3806(19) . ?
C4 H4 0.9400 . ?
C4 C5 1.382(2) . ?
C5 H5 0.9400 . ?
C5 C6 1.379(2) . ?
C6 C7 1.3884(19) . ?
C6 F1 1.230(5) . ?
C6 H6 0.9400(10) . ?
C7 H7 0.9400 . ?

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 113.31(16) 3_565 . ?
C1 N2 C2 121.11(7) . 11_565 ?
C1 N2 C2 121.11(7) . . ?
C2 N2 C2 117.78(13) 11_565 . ?
N1 C1 N1 126.69(16) 2_665 . ?
N1 C1 N2 116.65(8) 2_665 . ?
N1 C1 N2 116.66(8) . . ?
C3 C2 N2 120.78(11) . . ?
C7 C2 N2 119.12(11) . . ?
C7 C2 C3 120.08(12) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.90(13) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.47(14) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 120.3 . . ?
C6 C5 C4 119.33(13) . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C7 120.79(14) . . ?
C5 C6 H6 119(2) . . ?
C7 C6 H6 121(2) . . ?
F1 C6 C5 112.6(4) . . ?
F1 C6 C7 126.6(4) . . ?
C2 C7 C6 119.42(13) . . ?
C2 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?

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
N2 C2 C3 C4 179.71(12) . . . . ?
N2 C2 C7 C6 -179.28(12) . . . . ?
C1 N1 C1 N1 0.000(1) 3_565 . . 2_665 ?
C1 N1 C1 N2 179.998(1) 3_565 . . . ?
C1 N2 C2 C3 57.19(13) . . . . ?
C1 N2 C2 C7 -124.29(10) . . . . ?
C2 N2 C1 N1 9.14(6) 11_565 . . 2_665 ?
C2 N2 C1 N1 9.13(6) . . . . ?
C2 N2 C1 N1 -170.87(6) . . . 2_665 ?
C2 N2 C1 N1 -170.86(6) 11_565 . . . ?
C2 N2 C2 C3 -122.81(13) 11_565 . . . ?
C2 N2 C2 C7 55.70(10) 11_565 . . . ?
C2 C3 C4 C5 -0.4(2) . . . . ?
C3 C2 C7 C6 -0.75(19) . . . . ?
C3 C4 C5 C6 -0.8(2) . . . . ?
C4 C5 C6 C7 1.2(2) . . . . ?
C4 C5 C6 F1 179.7(5) . . . . ?
C5 C6 C7 C2 -0.5(2) . . . . ?
C7 C2 C3 C4 1.2(2) . . . . ?
F1 C6 C7 C2 -178.7(6) . . . . ?

_shelx_res_file                  
;
TITL 22_a.res in R-3c
    22_a.res
    created by SHELXL-2018/3 at 20:49:55 on 01-Nov-2022
REM Old TITL 22 in R-3c
REM SHELXT solution in R-3c: R1 0.191, Rweak 0.004, Alpha 0.024
REM <I/s> 0.351 for 127 systematic absences, Orientation as input
REM Formula found by SHELXT: C13 N2
CELL 0.71073 14.3814 14.3814 25.5525 90 90 120
ZERR 6 0.0004 0.0004 0.0013 0 0 0
LATT 3
SYMM -Y,+X-Y,+Z
SYMM +Y-X,-X,+Z
SYMM +Y,+X,0.5-Z
SYMM -Y+X,-Y,0.5-Z
SYMM -X,-X+Y,0.5-Z
SFAC C H F N
UNIT 234 174 6 36
DFIX 0.94 0.001 C6 H6

L.S. 10
PLAN  5
TEMP -63.15
CONF
BOND
LIST 4
MORE -1
BOND $H
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\22_a.hkl">
REM </olex2.extras>

WGHT    0.061100    1.405400
FVAR       0.43297
N1    4    0.333333    0.570722    0.416667    10.50000    0.02057    0.02113 =
         0.04865   -0.00053   -0.00106    0.01029
N2    4    0.518963    0.666667    0.416667    10.50000    0.01933    0.02000 =
         0.05310   -0.00410   -0.00205    0.01000
C1    1    0.423015    0.666667    0.416667    10.50000    0.02144    0.02258 =
         0.03714   -0.00121   -0.00060    0.01129
C2    1    0.521826    0.569227    0.409032    11.00000    0.01948    0.02150 =
         0.04479    0.00019    0.00309    0.01048
C3    1    0.477998    0.507427    0.364519    11.00000    0.02897    0.03099 =
         0.04964   -0.00595   -0.00611    0.01631
AFIX  43
H3    2    0.445609    0.528931    0.338948    11.00000   -1.20000
AFIX   0
C4    1    0.481982    0.414227    0.357792    11.00000    0.03193    0.03076 =
         0.05802   -0.01267   -0.00366    0.01490
AFIX  43
H4    2    0.451770    0.372163    0.327689    11.00000   -1.20000
AFIX   0
C5    1    0.530061    0.382349    0.394994    11.00000    0.03807    0.02570 =
         0.07125   -0.00173    0.00342    0.01918
AFIX  43
H5    2    0.531916    0.318414    0.390546    11.00000   -1.20000
AFIX   0
C6    1    0.575283    0.445256    0.438700    11.00000    0.03925    0.03263 =
         0.05719    0.00698    0.00194    0.02153
C7    1    0.571169    0.538765    0.446130    11.00000    0.02940    0.02981 =
         0.04139   -0.00008    0.00165    0.01512
AFIX  43
H7    2    0.601722    0.580961    0.476163    11.00000   -1.20000
AFIX   0
PART 1
F1    3    0.614748    0.407365    0.468649    10.16667    0.07126    0.04755 =
         0.05377    0.00230   -0.01670    0.04014
PART 2
H6    2    0.608212    0.423061    0.463647    10.83333   -1.20000
HKLF 4




REM  22_a.res in R-3c
REM wR2 = 0.1136, GooF = S = 1.040, Restrained GooF = 1.040 for all data
REM R1 = 0.0417 for 839 Fo > 4sig(Fo) and 0.0673 for all 1173 data
REM 82 parameters refined using 1 restraints

END

WGHT      0.0611      1.4054

REM Highest difference peak  0.163,  deepest hole -0.241,  1-sigma level  0.039
Q1    1   0.3802  0.2743  0.4135  11.00000  0.05    0.16
Q2    1   0.5104  0.6242  0.4217  11.00000  0.05    0.15
Q3    1   0.4805  0.6667  0.4167  10.50000  0.05    0.14
Q4    1   0.4558  0.3774  0.3921  11.00000  0.05    0.14
Q5    1   0.3378  0.5217  0.4364  11.00000  0.05    0.13
;
_shelx_res_checksum              86316
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_11_a
_database_code_depnum_ccdc_archive 'CCDC 2392815'
loop_
_audit_author_name
_audit_author_address
'Qiang Guo'
;Chengdu University of Information and Technology
China
;
_audit_update_record             
;
2024-11-27 deposited with the CCDC.	2024-12-09 downloaded from the CCDC.
;
_audit_creation_date             2022-11-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6396)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C39 H29 F1 N6'
_chemical_formula_sum            'C39 H29 F N6'
_chemical_formula_weight         600.68
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      trigonal
_space_group_IT_number           167
_space_group_name_H-M_alt        'R -3 c'
_space_group_name_Hall           '-R 3 2"c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z+1/2'
'x-y, -y, -z+1/2'
'-x, -x+y, -z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'y+2/3, x+1/3, -z+5/6'
'x-y+2/3, -y+1/3, -z+5/6'
'-x+2/3, -x+y+1/3, -z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'y+1/3, x+2/3, -z+7/6'
'x-y+1/3, -y+2/3, -z+7/6'
'-x+1/3, -x+y+2/3, -z+7/6'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-y, -x, z-1/2'
'-x+y, y, z-1/2'
'x, x-y, z-1/2'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-y+2/3, -x+1/3, z-1/6'
'-x+y+2/3, y+1/3, z-1/6'
'x+2/3, x-y+1/3, z-1/6'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
'-y+1/3, -x+2/3, z+1/6'
'-x+y+1/3, y+2/3, z+1/6'
'x+1/3, x-y+2/3, z+1/6'

_cell_length_a                   14.3978(4)
_cell_length_b                   14.3978(4)
_cell_length_c                   25.6230(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     4599.9(3)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    2708
_cell_measurement_temperature    298.00
_cell_measurement_theta_max      25.942
_cell_measurement_theta_min      2.829
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.990
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6649
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1300 before and 0.0596 after correction.
The Ratio of minimum to maximum transmission is 0.8918.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1884
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0655
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            13321
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_min         2.829
_diffrn_ambient_temperature      298.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                863
_reflns_number_total             1181
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         1181
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0414
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0516P)²+2.2395P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0960
_refine_ls_wR_factor_ref         0.1081
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All F(H) groups
2. Restrained distances
 C3-H3
 0.94 with sigma of 0.001
3. Others
 Fixed Sof: F1(0.16667) H3(0.83333)
4.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C6(H6), C4(H4), C5(H5)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N2 N 0.333333 0.57073(10) 0.416667 0.0312(4) Uani 1 2 d S T P . .
N1 N 0.51881(10) 0.666667 0.416667 0.0315(4) Uani 1 2 d S T P . .
C1 C 0.42307(12) 0.666667 0.416667 0.0281(4) Uani 1 2 d S T P . .
C2 C 0.61922(10) 0.76408(10) 0.42408(5) 0.0296(3) Uani 1 1 d . . . . .
C7 C 0.69914(11) 0.79521(11) 0.38698(6) 0.0350(4) Uani 1 1 d . . . . .
H7 H 0.687577 0.753551 0.357331 0.042 Uiso 1 1 calc R U . . .
C3 C 0.63820(11) 0.82578(11) 0.46863(6) 0.0366(4) Uani 1 1 d D . . . .
C6 C 0.79668(11) 0.88880(12) 0.39408(6) 0.0427(4) Uani 1 1 d . . . . .
H6 H 0.850460 0.909536 0.369168 0.051 Uiso 1 1 calc R U . . .
C4 C 0.73474(11) 0.91906(11) 0.47537(6) 0.0410(4) Uani 1 1 d . . . . .
H4 H 0.746500 0.960497 0.505125 0.049 Uiso 1 1 calc R U . . .
C5 C 0.81424(11) 0.95118(11) 0.43791(7) 0.0444(4) Uani 1 1 d . . . . .
H5 H 0.879165 1.014483 0.442252 0.053 Uiso 1 1 calc R U . . .
F1 F 0.5660(5) 0.7877(5) 0.5033(2) 0.0442(14) Uani 0.1667 1 d . . P A 1
H3 H 0.5835(17) 0.810(3) 0.4930(9) 0.053 Uiso 0.8333 1 d D U P B 2

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N2 0.0222(8) 0.0213(6) 0.0505(10) -0.0007(3) -0.0013(7) 0.0111(4)
N1 0.0204(6) 0.0216(8) 0.0527(10) -0.0044(7) -0.0022(3) 0.0108(4)
C1 0.0231(7) 0.0242(9) 0.0374(10) -0.0013(8) -0.0006(4) 0.0121(4)
C2 0.0221(6) 0.0216(6) 0.0461(8) -0.0004(6) -0.0032(6) 0.0117(5)
C7 0.0309(7) 0.0323(7) 0.0418(8) -0.0014(6) -0.0018(6) 0.0157(6)
C3 0.0283(7) 0.0317(7) 0.0504(9) -0.0039(7) 0.0008(6) 0.0154(6)
C6 0.0289(7) 0.0362(8) 0.0565(10) 0.0058(7) 0.0067(7) 0.0115(6)
C4 0.0344(8) 0.0315(8) 0.0567(9) -0.0120(7) -0.0086(7) 0.0162(6)
C5 0.0269(7) 0.0277(7) 0.0702(11) -0.0024(7) -0.0052(7) 0.0074(6)
F1 0.044(3) 0.033(3) 0.049(3) -0.004(3) 0.012(2) 0.014(3)

_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
N2 C1 1.3389(11) 3_565 ?
N2 C1 1.3389(11) . ?
N1 C1 1.378(2) . ?
N1 C2 1.4370(14) 11_565 ?
N1 C2 1.4371(14) . ?
C2 C7 1.3830(19) . ?
C2 C3 1.3872(19) . ?
C7 H7 0.9300 . ?
C7 C6 1.3887(19) . ?
C3 C4 1.378(2) . ?
C3 F1 1.266(5) . ?
C3 H3 0.9401(10) . ?
C6 H6 0.9300 . ?
C6 C5 1.380(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.384(2) . ?
C5 H5 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N2 C1 113.38(17) 3_565 . ?
C1 N1 C2 121.19(7) . . ?
C1 N1 C2 121.19(7) . 11_565 ?
C2 N1 C2 117.62(13) 11_565 . ?
N2 C1 N2 126.62(17) 2_665 . ?
N2 C1 N1 116.69(8) . . ?
N2 C1 N1 116.69(8) 2_665 . ?
C7 C2 N1 119.56(11) . . ?
C7 C2 C3 119.50(12) . . ?
C3 C2 N1 120.91(11) . . ?
C2 C7 H7 120.1 . . ?
C2 C7 C6 119.89(13) . . ?
C6 C7 H7 120.1 . . ?
C2 C3 H3 121.3(19) . . ?
C4 C3 C2 120.47(13) . . ?
C4 C3 H3 117.8(19) . . ?
F1 C3 C2 116.4(3) . . ?
F1 C3 C4 123.0(3) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 C7 120.35(14) . . ?
C5 C6 H6 119.8 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 120.09(14) . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 119.67(13) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C7 C6 -179.48(12) . . . . ?
N1 C2 C3 C4 180.00(12) . . . . ?
N1 C2 C3 F1 4.8(4) . . . . ?
C1 N2 C1 N2 0.0 3_565 . . 2_665 ?
C1 N2 C1 N1 180.0 3_565 . . . ?
C1 N1 C2 C7 -123.85(10) . . . . ?
C1 N1 C2 C3 57.98(13) . . . . ?
C2 N1 C1 N2 8.88(6) . . . 2_665 ?
C2 N1 C1 N2 8.88(6) 11_565 . . . ?
C2 N1 C1 N2 -171.12(6) 11_565 . . 2_665 ?
C2 N1 C1 N2 -171.11(6) . . . . ?
C2 N1 C2 C7 56.15(10) 11_565 . . . ?
C2 N1 C2 C3 -122.02(13) 11_565 . . . ?
C2 C7 C6 C5 -0.2(2) . . . . ?
C2 C3 C4 C5 -0.9(2) . . . . ?
C7 C2 C3 C4 1.8(2) . . . . ?
C7 C2 C3 F1 -173.4(4) . . . . ?
C7 C6 C5 C4 1.2(2) . . . . ?
C3 C2 C7 C6 -1.3(2) . . . . ?
C3 C4 C5 C6 -0.6(2) . . . . ?
F1 C3 C4 C5 174.0(4) . . . . ?

_shelx_res_file                  
;
TITL 11_a.res in R-3c
    11_a.res
    created by SHELXL-2018/3 at 20:42:51 on 01-Nov-2022
REM Old TITL 11 in R-3c
REM SHELXT solution in R-3c: R1 0.202, Rweak 0.006, Alpha 0.025
REM <I/s> 0.433 for 127 systematic absences, Orientation as input
REM Formula found by SHELXT: C13 N2
CELL 0.71073 14.3978 14.3978 25.623 90 90 120
ZERR 6 0.0004 0.0004 0.0011 0 0 0
LATT 3
SYMM -Y,+X-Y,+Z
SYMM +Y-X,-X,+Z
SYMM +Y,+X,0.5-Z
SYMM -Y+X,-Y,0.5-Z
SYMM -X,-X+Y,0.5-Z
SFAC C H F N
UNIT 234 174 6 36
DFIX 0.94 0.001 C3 H3

L.S. 10
PLAN  5
SIZE 0.12 0.1 0.08
TEMP 24.85
CONF
LIST 4
MORE -1
BOND $H
fmap 2
acta
OMIT -1 3 5
REM <olex2.extras>
REM <HklSrc "%.\\11_a.hkl">
REM </olex2.extras>

WGHT    0.051600    2.239500
FVAR       0.43436
N2    4    0.333333    0.570730    0.416667    10.50000    0.02216    0.02131 =
         0.05048   -0.00066   -0.00133    0.01108
N1    4    0.518815    0.666667    0.416667    10.50000    0.02043    0.02163 =
         0.05273   -0.00442   -0.00221    0.01082
C1    1    0.423072    0.666667    0.416667    10.50000    0.02309    0.02425 =
         0.03740   -0.00129   -0.00064    0.01212
C2    1    0.619216    0.764081    0.424078    11.00000    0.02209    0.02161 =
         0.04607   -0.00040   -0.00317    0.01168
C7    1    0.699138    0.795215    0.386981    11.00000    0.03086    0.03228 =
         0.04177   -0.00139   -0.00176    0.01572
AFIX  43
H7    2    0.687577    0.753551    0.357331    11.00000   -1.20000
AFIX   0
C3    1    0.638204    0.825776    0.468633    11.00000    0.02828    0.03170 =
         0.05042   -0.00394    0.00079    0.01543
C6    1    0.796684    0.888795    0.394080    11.00000    0.02894    0.03617 =
         0.05654    0.00582    0.00667    0.01146
AFIX  43
H6    2    0.850460    0.909536    0.369168    11.00000   -1.20000
AFIX   0
C4    1    0.734743    0.919061    0.475369    11.00000    0.03442    0.03153 =
         0.05667   -0.01204   -0.00861    0.01618
AFIX  43
H4    2    0.746500    0.960497    0.505125    11.00000   -1.20000
AFIX   0
C5    1    0.814241    0.951179    0.437908    11.00000    0.02693    0.02771 =
         0.07023   -0.00242   -0.00521    0.00737
AFIX  43
H5    2    0.879165    1.014483    0.442252    11.00000   -1.20000
AFIX   0
PART 1
F1    3    0.565969    0.787713    0.503335    10.16667    0.04390    0.03335 =
         0.04870   -0.00371    0.01191    0.01428
PART 2
H3    2    0.583498    0.810112    0.493008    10.83333   -1.20000
HKLF 4




REM  11_a.res in R-3c
REM wR2 = 0.1081, GooF = S = 1.040, Restrained GooF = 1.039 for all data
REM R1 = 0.0414 for 863 Fo > 4sig(Fo) and 0.0688 for all 1181 data
REM 82 parameters refined using 1 restraints

END

WGHT      0.0510      2.3193

REM Highest difference peak  0.147,  deepest hole -0.168,  1-sigma level  0.037
Q1    1   0.5685  0.7173  0.4125  11.00000  0.05    0.15
Q2    1   0.3333  0.4996  0.4167  10.50000  0.05    0.14
Q3    1   0.7946  1.0503  0.4617  11.00000  0.05    0.13
Q4    1   0.4781  0.6636  0.4359  11.00000  0.05    0.13
Q5    1   0.6563  0.8041  0.4031  11.00000  0.05    0.13
;
_shelx_res_checksum              61585
_olex2_submission_special_instructions 'No special instructions were received'
