# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_246_az_298k
_database_code_depnum_ccdc_archive 'CCDC 2144166'
loop_
_audit_author_name
_audit_author_address
'Hang Peng'
;Nanchang University
China
;
_audit_update_record             
;
2022-01-24 deposited with the CCDC.	2022-04-05 downloaded from the CCDC.
;
_audit_creation_date             2021-11-14
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H4 F6 N2'
_chemical_formula_sum            'C12 H4 F6 N2'
_chemical_formula_weight         290.17
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N F'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   4.4870(3)
_cell_length_b                   9.3652(6)
_cell_length_c                   13.1716(8)
_cell_angle_alpha                90
_cell_angle_beta                 97.270(6)
_cell_angle_gamma                90
_cell_volume                     549.04(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1296
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.2210
_cell_measurement_theta_min      2.6600
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.986
_exptl_absorpt_coefficient_mu    0.178
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52346
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.60a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.755
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4448
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.107
_diffrn_reflns_theta_min         2.676
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -29.00  43.00   0.50    2.00    --   20.00  54.00  60.00  144
  2  ω    -74.00  34.00   0.50    2.00    --   20.00  54.00  90.00  216
  3  ω     42.00  68.00   0.50    2.00    --   20.00  54.00  90.00   52
  4  ω    -72.00 -27.00   0.50    2.00    --   20.00  54.00   0.00   90
  5  ω     34.00 110.00   0.50    2.00    --   20.00  54.00   0.00  152
  6  ω    -30.00  -5.00   0.50    2.00    --   20.00  54.00-150.00   50
  7  ω     82.00 107.00   0.50    2.00    --   20.00  54.00-150.00   50
  8  ω    -69.00  44.00   0.50    2.00    --   20.00  54.00 -30.00  226
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0630564000
_diffrn_orient_matrix_UB_12      -0.0473783000
_diffrn_orient_matrix_UB_13      -0.0389106000
_diffrn_orient_matrix_UB_21      -0.0584879000
_diffrn_orient_matrix_UB_22      0.0590012000
_diffrn_orient_matrix_UB_23      -0.0299425000
_diffrn_orient_matrix_UB_31      0.1342088000
_diffrn_orient_matrix_UB_32      0.0034979000
_diffrn_orient_matrix_UB_33      -0.0231226000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                892
_reflns_number_total             1540
_reflns_odcompleteness_completeness 99.09
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.40.60a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.60a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.60a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         1540
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0915
_refine_ls_R_factor_gt           0.0485
_refine_ls_restrained_S_all      1.018
_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)+(0.0612P)²+0.0396P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1165
_refine_ls_wR_factor_ref         0.1367
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C008(H008), C00A(H00A)
;
_atom_sites_solution_hydrogens   geom
_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
F001 F 0.3676(3) 0.31724(14) 0.62408(8) 0.0634(4) Uani 1 1 d . . . . .
F002 F 0.1650(3) 0.42580(13) 0.27048(9) 0.0650(4) Uani 1 1 d . . . . .
F003 F 0.8326(3) 0.05644(12) 0.38425(11) 0.0654(4) Uani 1 1 d . . . . .
N004 N 0.0426(4) 0.49321(18) 0.45692(12) 0.0437(4) Uani 1 1 d . . . . .
C005 C 0.2456(4) 0.37696(19) 0.44786(13) 0.0356(4) Uani 1 1 d . . . . .
C006 C 0.4004(4) 0.2923(2) 0.52480(14) 0.0399(5) Uani 1 1 d . . . . .
C007 C 0.3068(4) 0.3468(2) 0.34798(14) 0.0414(5) Uani 1 1 d . . . . .
C008 C 0.5981(4) 0.18471(19) 0.50590(15) 0.0438(5) Uani 1 1 d . . . . .
H008 H 0.698287 0.130414 0.558675 0.053 Uiso 1 1 calc R U . . .
C009 C 0.6394(4) 0.16181(19) 0.40491(16) 0.0443(5) Uani 1 1 d . . . . .
C00A C 0.4974(4) 0.2400(2) 0.32430(15) 0.0471(5) Uani 1 1 d . . . . .
H00A H 0.528766 0.221489 0.257094 0.057 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F001 C006 1.355(2) . ?
F002 C007 1.353(2) . ?
F003 C009 1.364(2) . ?
N004 N004 1.249(3) 3_566 ?
N004 C005 1.434(2) . ?
C005 C006 1.400(2) . ?
C005 C007 1.406(2) . ?
C006 C008 1.386(2) . ?
C007 C00A 1.377(3) . ?
C008 H008 0.9300 . ?
C008 C009 1.383(3) . ?
C009 C00A 1.378(3) . ?
C00A H00A 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
N004 N004 C005 115.1(2) 3_566 . ?
C006 C005 N004 129.18(17) . . ?
C006 C005 C007 115.19(16) . . ?
C007 C005 N004 115.58(15) . . ?
F001 C006 C005 119.78(17) . . ?
F001 C006 C008 116.68(17) . . ?
C008 C006 C005 123.50(17) . . ?
F002 C007 C005 117.83(16) . . ?
F002 C007 C00A 118.21(17) . . ?
C00A C007 C005 123.94(17) . . ?
C006 C008 H008 121.6 . . ?
C009 C008 C006 116.90(18) . . ?
C009 C008 H008 121.6 . . ?
F003 C009 C008 118.05(18) . . ?
F003 C009 C00A 118.32(19) . . ?
C00A C009 C008 123.63(18) . . ?
C007 C00A C009 116.82(18) . . ?
C007 C00A H00A 121.6 . . ?
C009 C00A H00A 121.6 . . ?

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
F001 C006 C008 C009 -178.05(15) . . . . ?
F002 C007 C00A C009 179.72(16) . . . . ?
F003 C009 C00A C007 -179.18(16) . . . . ?
N004 N004 C005 C006 -12.0(3) 3_566 . . . ?
N004 N004 C005 C007 170.6(2) 3_566 . . . ?
N004 C005 C006 F001 -0.5(3) . . . . ?
N004 C005 C006 C008 -178.20(16) . . . . ?
N004 C005 C007 F002 -1.8(2) . . . . ?
N004 C005 C007 C00A 179.54(17) . . . . ?
C005 C006 C008 C009 -0.2(3) . . . . ?
C005 C007 C00A C009 -1.6(3) . . . . ?
C006 C005 C007 F002 -179.61(16) . . . . ?
C006 C005 C007 C00A 1.7(3) . . . . ?
C006 C008 C009 F003 -179.94(15) . . . . ?
C006 C008 C009 C00A 0.4(3) . . . . ?
C007 C005 C006 F001 177.00(15) . . . . ?
C007 C005 C006 C008 -0.7(3) . . . . ?
C008 C009 C00A C007 0.5(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.151
_oxdiff_exptl_absorpt_empirical_full_min 0.720
####################################################################### 
# 
# 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_P21
_database_code_depnum_ccdc_archive 'CCDC 2144165'
loop_
_audit_author_name
_audit_author_address
'Hang Peng'
;Nanchang University
China
;
_audit_update_record             
;
2022-01-25 deposited with the CCDC.	2022-04-05 downloaded from the CCDC.
;
_audit_creation_date             2021-11-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H6 F5 N3'
_chemical_formula_sum            'C12 H6 F5 N3'
_chemical_formula_weight         287.20
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N F'
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'
F F 0.0727 0.0534 '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'

_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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   3.76719(12)
_cell_length_b                   6.2632(2)
_cell_length_c                   24.1516(7)
_cell_angle_alpha                90
_cell_angle_beta                 92.008(3)
_cell_angle_gamma                90
_cell_volume                     569.50(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2232
_cell_measurement_temperature    298(17)
_cell_measurement_theta_max      75.8620
_cell_measurement_theta_min      3.5740
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.437
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69192
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.108a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.675
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             288
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0115
_diffrn_reflns_av_unetI/netI     0.0071
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.933
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            2826
_diffrn_reflns_point_group_measured_fraction_full 0.741
_diffrn_reflns_point_group_measured_fraction_max 0.689
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.045
_diffrn_reflns_theta_min         1.830
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297.96(17)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     24.00 111.00   0.50    0.80    --   45.15  72.00 -81.00  174
  2  ω     84.00 171.00   0.50    0.80    --  107.00  72.00 -81.00  174
  3  ω    131.00 157.00   0.50    0.80    --  107.00  15.00-150.00   52
  4  ω     83.00 125.00   0.50    0.80    --  107.00  15.00-150.00   84
  5  ω     38.00 105.00   0.50    0.80    --  107.00 -94.00   0.00  134
  6  ω    -21.00   4.00   0.50    0.80    --  -45.15  72.00 -81.00   50
  7  ω    -22.00  33.00   0.50    0.80    --  -45.15  19.00 -90.00  110
  8  ω    -20.00   5.00   0.50    0.80    --   45.15 -72.00 148.00   50
  9  ω     11.00  48.00   0.50    0.80    --   45.15 -72.00 148.00   74
 10  ω     42.00  85.00   0.50    0.80    --  107.00 -72.00 148.00   86
 11  ω     34.00  59.00   0.50    0.80    --  107.00 -61.00   0.00   50
 12  ω     42.00  67.00   0.50    0.80    --  107.00 -61.00-180.00   50
 13  ω    -89.00 -34.00   0.50    0.80    -- -102.00  72.00 -81.00  110
 14  ω    -62.00 -28.00   0.50    0.80    -- -102.00  61.00 -90.00   68
 15  ω    -69.00 -31.00   0.50    0.80    -- -102.00  61.00   0.00   76
 16  ω    -68.00 -29.00   0.50    0.80    -- -102.00  61.00 120.00   78
 17  ω   -151.00-126.00   0.50    0.80    -- -102.00 -72.00 148.00   50
 18  ω   -173.00-129.00   0.50    0.80    -- -102.00 -45.00-150.00   88
 19  ω   -113.00 -88.00   0.50    0.80    -- -102.00 -45.00-150.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0641814000
_diffrn_orient_matrix_UB_12      0.1662481000
_diffrn_orient_matrix_UB_13      0.0463100000
_diffrn_orient_matrix_UB_21      0.2850799000
_diffrn_orient_matrix_UB_22      0.1084277000
_diffrn_orient_matrix_UB_23      -0.0344727000
_diffrn_orient_matrix_UB_31      -0.2862742000
_diffrn_orient_matrix_UB_32      0.1454129000
_diffrn_orient_matrix_UB_33      -0.0272166000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.349
_reflns_Friedel_fraction_full    0.442
_reflns_Friedel_fraction_max     0.394
_reflns_number_gt                1503
_reflns_number_total             1645
_reflns_odcompleteness_completeness 98.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.41.108a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.108a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.108a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details 
;
 Flack x determined using 390 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.35(15)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         1645
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0539
_refine_ls_restrained_S_all      1.176
_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)+(0.0932P)²+0.1617P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1505
_refine_ls_wR_factor_ref         0.1575
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2. Restrained distances
 N3-C12
 1.48 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
F1 \\sim C2: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.01
within 2A
4.a Rotating group:
 N3(H3A,H3B)
4.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C5(H5), C9(H9), C3(H3)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
F3 F -0.8681(6) -0.7793(6) -0.35800(10) 0.0641(8) Uani 1 1 d . . . . .
F4 F -1.1292(6) -1.3686(6) -0.14231(9) 0.0634(8) Uani 1 1 d . . . . .
C1 C -1.0913(8) -1.0932(9) -0.32233(13) 0.0402(11) Uani 1 1 d . . . . .
C12 C -0.7426(9) -0.8548(11) -0.16660(15) 0.0500(12) Uani 1 1 d D . . . .
F5 F -0.6183(6) -0.8762(8) -0.01774(7) 0.0750(11) Uani 1 1 d . . . . .
N3 N -0.6625(8) -0.7106(6) -0.20729(10) 0.0492(9) Uani 1 1 d D . . . .
H3A H -0.821119 -0.717258 -0.233893 0.059 Uiso 1 1 d R U . . .
H3B H -0.661448 -0.583568 -0.193453 0.059 Uiso 1 1 d R U . . .
N1 N -1.0308(7) -1.1300(7) -0.22944(11) 0.0435(9) Uani 1 1 d . . . . .
F2 F -1.3865(6) -1.2643(8) -0.48184(7) 0.0777(12) Uani 1 1 d . . . . .
C11 C -0.6493(9) -0.7934(11) -0.11194(14) 0.0538(12) Uani 1 1 d . . . . .
H11 H -0.548606 -0.660472 -0.104416 0.065 Uiso 1 1 calc R U . . .
N2 N -0.9761(7) -1.0143(8) -0.27120(11) 0.0492(11) Uani 1 1 d . . . . .
C5 C -1.1250(9) -1.0126(11) -0.42115(15) 0.0533(14) Uani 1 1 d . . . . .
H5 H -1.084896 -0.918412 -0.450033 0.064 Uiso 1 1 calc R U . . .
F1 F -1.3298(8) -1.4272(6) -0.29333(10) 0.0828(11) Uani 1 1 d . U . . .
C4 C -1.2837(9) -1.2111(11) -0.42935(14) 0.0504(14) Uani 1 1 d . . . . .
C9 C -0.8724(9) -1.1256(10) -0.07872(15) 0.0511(13) Uani 1 1 d . . . . .
H9 H -0.915985 -1.216408 -0.049250 0.061 Uiso 1 1 calc R U . . .
C6 C -1.0333(9) -0.9674(10) -0.36747(16) 0.0444(11) Uani 1 1 d . . . . .
C7 C -0.9065(9) -1.0427(10) -0.17851(13) 0.0431(12) Uani 1 1 d . . . . .
C8 C -0.9693(9) -1.1803(10) -0.13245(15) 0.0479(14) Uani 1 1 d . . . . .
C2 C -1.2613(9) -1.2989(9) -0.33407(13) 0.0442(10) Uani 1 1 d . U . . .
C3 C -1.3579(9) -1.3515(10) -0.38801(13) 0.0507(11) Uani 1 1 d . . . . .
H3 H -1.471450 -1.480150 -0.396087 0.061 Uiso 1 1 calc R U . . .
C10 C -0.7107(9) -0.9336(12) -0.07057(14) 0.0556(18) 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
F3 C6 1.348(7) . ?
F4 C8 1.342(7) . ?
C1 N2 1.386(4) . ?
C1 C6 1.369(7) . ?
C1 C2 1.462(7) . ?
C12 N3 1.376(5) . ?
C12 C11 1.408(5) . ?
C12 C7 1.355(8) . ?
F5 C10 1.359(4) . ?
N3 H3A 0.8630 . ?
N3 H3B 0.8632 . ?
N1 N2 1.265(3) . ?
N1 C7 1.411(5) . ?
F2 C4 1.354(4) . ?
C11 H11 0.9300 . ?
C11 C10 1.356(7) . ?
C5 H5 0.9300 . ?
C5 C4 1.391(10) . ?
C5 C6 1.360(5) . ?
F1 C2 1.303(5) . ?
C4 C3 1.366(7) . ?
C9 H9 0.9300 . ?
C9 C8 1.379(5) . ?
C9 C10 1.359(9) . ?
C7 C8 1.433(7) . ?
C2 C3 1.380(5) . ?
C3 H3 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
N2 C1 C2 127.5(4) . . ?
C6 C1 N2 116.8(5) . . ?
C6 C1 C2 115.7(3) . . ?
N3 C12 C11 115.9(5) . . ?
C7 C12 N3 121.9(4) . . ?
C7 C12 C11 122.2(5) . . ?
C12 N3 H3A 109.7 . . ?
C12 N3 H3B 109.1 . . ?
H3A N3 H3B 109.0 . . ?
N2 N1 C7 114.5(3) . . ?
C12 C11 H11 121.0 . . ?
C10 C11 C12 118.1(5) . . ?
C10 C11 H11 121.0 . . ?
N1 N2 C1 116.8(4) . . ?
C4 C5 H5 122.7 . . ?
C6 C5 H5 122.7 . . ?
C6 C5 C4 114.6(5) . . ?
F2 C4 C5 117.4(4) . . ?
F2 C4 C3 117.8(5) . . ?
C3 C4 C5 124.7(4) . . ?
C8 C9 H9 121.4 . . ?
C10 C9 H9 121.4 . . ?
C10 C9 C8 117.3(5) . . ?
F3 C6 C1 117.0(4) . . ?
F3 C6 C5 116.4(5) . . ?
C5 C6 C1 126.6(5) . . ?
C12 C7 N1 131.0(4) . . ?
C12 C7 C8 116.3(4) . . ?
N1 C7 C8 112.6(5) . . ?
F4 C8 C9 119.2(4) . . ?
F4 C8 C7 118.4(4) . . ?
C9 C8 C7 122.4(5) . . ?
F1 C2 C1 119.6(3) . . ?
F1 C2 C3 120.9(5) . . ?
C3 C2 C1 119.5(4) . . ?
C4 C3 C2 118.8(5) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
F5 C10 C9 117.9(5) . . ?
C11 C10 F5 118.4(5) . . ?
C11 C10 C9 123.6(4) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N3 H3A N2 0.86 2.14 2.696(6) 121.8 . yes

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 C2 C3 C4 1.6(6) . . . . ?
C12 C11 C10 F5 179.4(4) . . . . ?
C12 C11 C10 C9 -3.3(7) . . . . ?
C12 C7 C8 F4 -179.6(4) . . . . ?
C12 C7 C8 C9 0.6(6) . . . . ?
N3 C12 C11 C10 -177.5(4) . . . . ?
N3 C12 C7 N1 -1.2(7) . . . . ?
N3 C12 C7 C8 178.9(4) . . . . ?
N1 C7 C8 F4 0.5(6) . . . . ?
N1 C7 C8 C9 -179.4(4) . . . . ?
F2 C4 C3 C2 -178.8(4) . . . . ?
C11 C12 C7 N1 177.7(4) . . . . ?
C11 C12 C7 C8 -2.2(7) . . . . ?
N2 C1 C6 F3 0.4(5) . . . . ?
N2 C1 C6 C5 -179.7(4) . . . . ?
N2 C1 C2 F1 2.4(6) . . . . ?
N2 C1 C2 C3 -179.8(4) . . . . ?
N2 N1 C7 C12 1.0(6) . . . . ?
N2 N1 C7 C8 -179.2(3) . . . . ?
C5 C4 C3 C2 -2.1(7) . . . . ?
F1 C2 C3 C4 179.4(4) . . . . ?
C4 C5 C6 F3 177.9(4) . . . . ?
C4 C5 C6 C1 -2.0(6) . . . . ?
C6 C1 N2 N1 179.7(3) . . . . ?
C6 C1 C2 F1 -179.2(4) . . . . ?
C6 C1 C2 C3 -1.4(6) . . . . ?
C6 C5 C4 F2 179.0(4) . . . . ?
C6 C5 C4 C3 2.2(6) . . . . ?
C7 C12 C11 C10 3.5(7) . . . . ?
C7 N1 N2 C1 179.7(4) . . . . ?
C8 C9 C10 F5 179.1(4) . . . . ?
C8 C9 C10 C11 1.7(7) . . . . ?
C2 C1 N2 N1 -1.9(5) . . . . ?
C2 C1 C6 F3 -178.2(3) . . . . ?
C2 C1 C6 C5 1.7(6) . . . . ?
C10 C9 C8 F4 179.9(4) . . . . ?
C10 C9 C8 C7 -0.3(7) . . . . ?


# start Validation Reply Form

_vrf_PLAT111_P21                 
;
PROBLEM: ADDSYM Detects New (Pseudo) Centre of Symmetry .        100 %Fit   

RESPONSE: Our compound have SHG  (second-harmonic generation) effect 
and thus cannot crystallize in a centrosymmetric space group P21/c.
;
_vrf_PLAT112_P21                 
;
PROBLEM: ADDSYM Detects New (Pseudo) Symm. Elem         c        100 %Fit 

RESPONSE: Our compound have SHG  (second-harmonic generation) effect 
and thus cannot crystallize in a centrosymmetric space group P21/c.
;
_vrf_PLAT113_P21                 
;
PROBLEM: ADDSYM Suggests Possible Pseudo/New  Space Group      P21/c Check 

RESPONSE: Our compound have SHG  (second-harmonic generation) effect 
and thus cannot crystallize in a centrosymmetric space group P21/c.
;
# end Validation Reply Form






_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.729
_oxdiff_exptl_absorpt_empirical_full_min 0.663
