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

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

data_exp_948
_database_code_depnum_ccdc_archive 'CCDC 2475422'
loop_
_audit_author_name
_audit_author_address
'Takumi Matsuo'
;Kochi University of Technology
Japan
;
_audit_update_record             
;
2025-07-24 deposited with the CCDC.	2025-11-03 downloaded from the CCDC.
;
_audit_creation_date             2025-01-24
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H16 F2'
_chemical_formula_sum            'C22 H16 F2'
_chemical_formula_weight         318.35
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'

_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   12.1905(8)
_cell_length_b                   5.5640(4)
_cell_length_c                   22.9175(15)
_cell_angle_alpha                90
_cell_angle_beta                 92.155(6)
_cell_angle_gamma                90
_cell_volume                     1553.35(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2637
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      29.4290
_cell_measurement_theta_min      3.3350
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.464
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             664
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.2364
-1 1 1 0.2803
-1 0 1 0.3366
1 0 -1 0.3366
0 0 1 0.0161
0 0 -1 0.0329
1 1 -1 0.3378

_exptl_crystal_preparation       'mounted using grease'
_exptl_crystal_recrystallization_method 'in soln phase'
_exptl_crystal_size_max          0.776
_exptl_crystal_size_mid          0.583
_exptl_crystal_size_min          0.049
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0003 -0.9996 0.0008 -0.0848 0.0506 0.0806
-0.9995 1.0001 1.0061 0.1215 -0.0691 -0.0303
-0.9992 0.0005 1.0069 0.0367 -0.0185 0.0502
0.9992 -0.0005 -1.0069 -0.0367 0.0185 -0.0502
0.0002 0.0000 1.0014 -0.0057 -0.0282 0.0116
-0.0002 -0.0000 -1.0014 0.0057 0.0282 -0.0116
0.9990 0.9992 -1.0076 0.0481 -0.0321 -0.1308

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            4475
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.356
_diffrn_reflns_theta_min         3.345
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -11.00  88.00   0.50   30.23    --   12.72  68.00  35.00  198
  2  ω     42.00  95.00   0.50   30.23    --   12.72 178.00-120.00  106
  3  ω    -68.00  21.00   0.50   30.23    --   12.72 -37.00 -90.00  178
  4  ω    -47.00 -22.00   0.50   30.23    --   12.72 -68.00 -97.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0424728000
_diffrn_orient_matrix_UB_12      0.0848190000
_diffrn_orient_matrix_UB_13      -0.0057269000
_diffrn_orient_matrix_UB_21      -0.0098481000
_diffrn_orient_matrix_UB_22      -0.0506661000
_diffrn_orient_matrix_UB_23      -0.0281178000
_diffrn_orient_matrix_UB_31      -0.0385865000
_diffrn_orient_matrix_UB_32      -0.0805811000
_diffrn_orient_matrix_UB_33      0.0116267000
_diffrn_oxdiff_digest_frames     
;
0156807c36d1480feaa37d7aab8a51db8f005329052
;
_diffrn_oxdiff_digest_hkl        
;
0149608879f5fba5c06d5297bbea338fd2acbc
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1351
_reflns_number_total             1573
_reflns_odcompleteness_completeness 99.89
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.622
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.126
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1573
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1329
_refine_ls_R_factor_gt           0.1260
_refine_ls_restrained_S_all      1.114
_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)+(0.0311P)²+46.7178P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3039
_refine_ls_wR_factor_ref         0.3061
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C003(H003), C004(H004), C005(H005), C006(H006), C007(H007), C008(H008),
 C009(H009), C00C(H00C)
;
_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 0.6098(3) 0.3854(7) 0.54374(16) 0.0230(9) Uani 1 1 d . . . . .
C002 C 0.2405(5) 0.4873(11) 0.6353(3) 0.0186(13) Uani 1 1 d . . . . .
C003 C 0.2396(5) 0.8473(12) 0.6936(3) 0.0238(14) Uani 1 1 d . . . . .
H003 H 0.277426 0.982291 0.709900 0.029 Uiso 1 1 calc R . . . .
C004 C 0.6076(5) 0.0435(11) 0.4845(3) 0.0170(12) Uani 1 1 d . . . . .
H004 H 0.680961 0.077827 0.474757 0.020 Uiso 1 1 calc R . . . .
C005 C 0.1294(5) 0.8130(12) 0.7054(3) 0.0240(14) Uani 1 1 d . . . . .
H005 H 0.091742 0.925005 0.728655 0.029 Uiso 1 1 calc R . . . .
C006 C 0.1303(5) 0.4522(12) 0.6478(3) 0.0197(13) Uani 1 1 d . . . . .
H006 H 0.092079 0.316335 0.632254 0.024 Uiso 1 1 calc R . . . .
C007 C 0.2928(5) 0.3188(11) 0.5961(3) 0.0214(13) Uani 1 1 d . . . . .
H007 H 0.249260 0.187889 0.582162 0.026 Uiso 1 1 calc R . . . .
C008 C 0.0763(5) 0.6144(13) 0.6827(3) 0.0242(14) Uani 1 1 d . . . . .
H008 H 0.001554 0.587609 0.691069 0.029 Uiso 1 1 calc R . . . .
C009 C 0.2945(5) 0.6900(12) 0.6590(3) 0.0225(13) Uani 1 1 d . . . . .
H009 H 0.369399 0.718153 0.651156 0.027 Uiso 1 1 calc R . . . .
C00A C 0.5538(5) 0.1942(11) 0.5218(3) 0.0188(13) Uani 1 1 d . . . . .
C00B C 0.4453(5) 0.1593(11) 0.5390(3) 0.0180(13) Uani 1 1 d . . . . .
C00C C 0.3955(5) 0.3294(11) 0.5780(3) 0.0201(13) Uani 1 1 d . . . . .
H00C H 0.439723 0.459468 0.591852 0.024 Uiso 1 1 calc R . . . .


_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 C00A 1.351(7) . ?
C002 C006 1.398(8) . ?
C002 C007 1.460(8) . ?
C002 C009 1.405(9) . ?
C003 C005 1.392(9) . ?
C003 C009 1.373(9) . ?
C004 C00A 1.380(8) . ?
C004 C00B 1.397(8) 5_656 ?
C005 C008 1.373(10) . ?
C006 C008 1.389(9) . ?
C007 C00C 1.334(8) . ?
C00A C00B 1.408(8) . ?
C00B C00C 1.451(8) . ?

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
C006 C002 C007 118.8(6) . . ?
C006 C002 C009 118.2(6) . . ?
C009 C002 C007 123.0(5) . . ?
C009 C003 C005 121.3(6) . . ?
C00A C004 C00B 120.4(5) . 5_656 ?
C008 C005 C003 118.8(6) . . ?
C008 C006 C002 120.5(6) . . ?
C00C C007 C002 126.8(6) . . ?
C005 C008 C006 120.9(6) . . ?
C003 C009 C002 120.3(6) . . ?
F001 C00A C004 117.7(5) . . ?
F001 C00A C00B 118.1(5) . . ?
C004 C00A C00B 124.2(6) . . ?
C004 C00B C00A 115.4(5) 5_656 . ?
C004 C00B C00C 124.5(5) 5_656 . ?
C00A C00B C00C 120.1(5) . . ?
C007 C00C C00B 125.6(6) . . ?

_olex2_exptl_crystal_mounting_method 'mounted on loop mounter'
_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 1.426
_oxdiff_exptl_absorpt_empirical_full_min 0.736
####################################################################### 
# 
# 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_exp_1158
_database_code_depnum_ccdc_archive 'CCDC 2475426'
loop_
_audit_author_name
_audit_author_address
'Takumi Matsuo'
;Kochi University of Technology
Japan
;
_audit_update_record             
;
2025-07-24 deposited with the CCDC.	2025-11-03 downloaded from the CCDC.
;
_audit_creation_date             2025-07-03
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H16 F2'
_chemical_formula_sum            'C22 H16 F2'
_chemical_formula_weight         318.35
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'

_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/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   5.9413(7)
_cell_length_b                   7.5785(6)
_cell_length_c                   37.009(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.336(10)
_cell_angle_gamma                90
_cell_volume                     1627.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2165
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      26.9900
_cell_measurement_theta_min      2.2480
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.942
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.613
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             664
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 0 0.3481
1 0 0 0.2933
0 0 1 0.0376
0 0 -1 0.0207
0 1 -1 0.2105
0 -2 1 0.2111

_exptl_crystal_preparation       'mounted using grease'
_exptl_crystal_recrystallization_method 
'sublimation under nitrogen gas flow at 320 deg centigrade'
_exptl_crystal_size_max          0.67
_exptl_crystal_size_mid          0.438
_exptl_crystal_size_min          0.058
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.0010 -0.0003 -0.0059 -0.1192 -0.0249 0.0107
1.0010 0.0003 0.0059 0.1192 0.0249 -0.0107
0.0001 -0.0002 0.9996 0.0080 -0.0179 -0.0002
-0.0001 0.0002 -0.9996 -0.0080 0.0179 0.0002
-0.0003 1.0004 -1.0040 -0.0003 0.0208 0.0934
0.0005 -2.0007 1.0084 -0.0074 -0.0237 -0.1867

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_unetI/netI     0.0442
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            10326
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.253
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -47.00  95.00   0.50   19.76    --   12.72   7.00 -69.00  284
  2  ω     33.00  58.00   0.50   19.76    --   12.72 -99.00 -90.00   50
  3  ω     -8.00  17.00   0.50   19.76    --   12.72 -99.00 -90.00   50
  4  ω      2.00  28.00   0.50   19.76    --  -13.34 -99.00  60.00   52
  5  ω    -72.00 -40.00   0.50   19.76    --   12.72  -7.00 114.00   64
  6  ω     54.00  95.00   0.50   19.76    --   12.72 178.00  60.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1190315000
_diffrn_orient_matrix_UB_12      0.0077869000
_diffrn_orient_matrix_UB_13      0.0080436000
_diffrn_orient_matrix_UB_21      0.0250215000
_diffrn_orient_matrix_UB_22      0.0028046000
_diffrn_orient_matrix_UB_23      -0.0179010000
_diffrn_orient_matrix_UB_31      -0.0107419000
_diffrn_orient_matrix_UB_32      0.0932528000
_diffrn_orient_matrix_UB_33      -0.0001360000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1368
_reflns_number_total             3323
_reflns_odcompleteness_completeness 99.61
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (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         -0.157
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.0050(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3323
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.1444
_refine_ls_R_factor_gt           0.0578
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0788P)²+0.1399P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1554
_refine_ls_wR_factor_ref         0.2003
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C006-C00N \\sim C006-C1
 with sigma of 0.02
 C009-C00O \\sim C009-C00P
 with sigma of 0.02
 C006-C00O \\sim C006-C00P
 with sigma of 0.04
 C00N-C00O \\sim C1-C00P
 with sigma of 0.02
 C009-C00N \\sim C009-C1
 with sigma of 0.04
 C00A-C00M \\sim C00A-C2
 with sigma of 0.04
 C003-C00M \\sim C003-C2
 with sigma of 0.02
 C00A-C00L \\sim C00A-C3
 with sigma of 0.02
 C003-C00L \\sim C003-C3
 with sigma of 0.04
 C00L-C00M \\sim C3-C2
 with sigma of 0.02
3. Others
 Sof(C00P)=Sof(H00P)=Sof(C1)=Sof(H1)=1-FVAR(1)
 Sof(C00N)=Sof(H00N)=Sof(C00O)=Sof(H00O)=FVAR(1)
 Sof(C2)=Sof(H2)=Sof(C3)=Sof(H3)=1-FVAR(2)
 Sof(C00L)=Sof(H00L)=Sof(C00M)=Sof(H00M)=FVAR(2)
4.a Aromatic/amide H refined with riding coordinates:
 C004(H004), C005(H005), C007(H007), C008(H008), C00B(H00B), C00C(H00C),
 C00D(H00D), C00F(H00F), C00G(H00G), C00I(H00I), C00J(H00J), C00K(H00K),
 C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P), C1(H1), C2(H2),
 C3(H3)
;
_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 -0.2748(4) 0.5728(2) 0.02215(4) 0.1395(8) Uani 1 1 d . . . . .
F002 F 1.7654(4) 0.5527(2) 0.48164(5) 0.1561(9) Uani 1 1 d . . . . .
C003 C 0.9057(5) 0.5729(3) 0.28580(7) 0.0710(7) Uani 1 1 d D . . . .
C004 C 0.5468(4) 0.6543(3) 0.24697(8) 0.0715(7) Uani 1 1 d . . . . .
H004 H 0.400983 0.709990 0.244439 0.086 Uiso 1 1 calc R U . . .
C005 C 0.9642(5) 0.4968(3) 0.25513(9) 0.0799(8) Uani 1 1 d . . . . .
H005 H 1.109810 0.440929 0.257657 0.096 Uiso 1 1 calc R U . . .
C006 C 0.6051(5) 0.5785(3) 0.21616(7) 0.0700(7) Uani 1 1 d D . . . .
C007 C 0.6919(5) 0.6513(3) 0.28058(7) 0.0719(7) Uani 1 1 d . . . . .
H007 H 0.645315 0.704439 0.301048 0.086 Uiso 1 1 calc R U . . .
C008 C 0.8183(5) 0.5002(3) 0.22148(7) 0.0781(8) Uani 1 1 d . . . . .
H008 H 0.864916 0.446985 0.201015 0.094 Uiso 1 1 calc R U . . .
C009 C 0.1601(5) 0.5693(3) 0.12378(7) 0.0805(8) Uani 1 1 d D . . . .
C00A C 1.3482(5) 0.5762(3) 0.37893(7) 0.0787(8) Uani 1 1 d D . . . .
C00B C -0.0537(5) 0.6477(3) 0.11848(7) 0.0792(8) Uani 1 1 d . . . . .
H00B H -0.101156 0.700854 0.138878 0.095 Uiso 1 1 calc R U . . .
C00C C 1.2846(5) 0.6489(3) 0.40967(8) 0.0826(8) Uani 1 1 d . . . . .
H00C H 1.139578 0.706289 0.406686 0.099 Uiso 1 1 calc R U . . .
C00D C -0.1978(5) 0.6504(3) 0.08461(8) 0.0809(8) Uani 1 1 d . . . . .
H00D H -0.344172 0.706020 0.081260 0.097 Uiso 1 1 calc R U . . .
C00E C -0.1301(6) 0.5727(3) 0.05560(7) 0.0803(8) Uani 1 1 d . . . . .
C00F C 0.2198(5) 0.4907(3) 0.09338(9) 0.0910(9) Uani 1 1 d . . . . .
H00F H 0.364908 0.433566 0.096361 0.109 Uiso 1 1 calc R U . . .
C00G C 1.5605(6) 0.4971(3) 0.38426(8) 0.0884(9) Uani 1 1 d . . . . .
H00G H 1.609881 0.447379 0.363689 0.106 Uiso 1 1 calc R U . . .
C00H C 1.6282(6) 0.5603(3) 0.44763(8) 0.0889(8) Uani 1 1 d . . . . .
C00I C 1.7017(5) 0.4884(3) 0.41834(10) 0.0929(9) Uani 1 1 d . . . . .
H00I H 1.848400 0.433360 0.421722 0.111 Uiso 1 1 calc R U . . .
C00J C 1.4235(6) 0.6405(3) 0.44388(7) 0.0902(9) Uani 1 1 d . . . . .
H00J H 1.376732 0.690228 0.464672 0.108 Uiso 1 1 calc R U . . .
C00K C 0.0766(6) 0.4928(4) 0.05937(8) 0.0944(9) Uani 1 1 d . . . . .
H00K H 0.121081 0.439283 0.038758 0.113 Uiso 1 1 calc R U . . .
C00L C 1.2355(10) 0.5510(7) 0.33944(16) 0.072(2) Uani 0.605(9) 1 d D . P A 1
H00L H 1.320984 0.499097 0.323239 0.086 Uiso 0.605(9) 1 calc R U P A 1
C00M C 1.0218(9) 0.5984(7) 0.32630(18) 0.0674(19) Uani 0.605(9) 1 d D . P A 1
H00M H 0.936570 0.650294 0.342534 0.081 Uiso 0.605(9) 1 calc R U P A 1
C00N C 0.4902(10) 0.5518(7) 0.17700(16) 0.0685(19) Uani 0.607(9) 1 d D . P B 1
H00N H 0.573952 0.498386 0.160718 0.082 Uiso 0.607(9) 1 calc R U P B 1
C00O C 0.2774(10) 0.5994(7) 0.16418(18) 0.0735(19) Uani 0.607(9) 1 d D . P B 1
H00O H 0.193569 0.653941 0.180312 0.088 Uiso 0.607(9) 1 calc R U P B 1
C00P C 0.3704(14) 0.5348(8) 0.15233(17) 0.052(2) Uani 0.393(9) 1 d D . P B 2
H00P H 0.488111 0.459776 0.147278 0.063 Uiso 0.393(9) 1 calc R U P B 2
C1 C 0.3916(16) 0.6114(9) 0.18549(18) 0.054(2) Uani 0.393(9) 1 d D . P B 2
H1 H 0.273019 0.686867 0.190025 0.064 Uiso 0.393(9) 1 calc R U P B 2
C2 C 1.1153(16) 0.5384(9) 0.31460(18) 0.060(2) Uani 0.395(9) 1 d D . P A 2
H2 H 1.232873 0.462923 0.309702 0.072 Uiso 0.395(9) 1 calc R U P A 2
C3 C 1.1361(17) 0.6151(9) 0.34748(18) 0.058(2) Uani 0.395(9) 1 d D . P A 2
H3 H 1.020391 0.694199 0.351711 0.069 Uiso 0.395(9) 1 calc R 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
F001 C00E 1.348(3) . ?
F002 C00H 1.347(3) . ?
C003 C005 1.382(3) . ?
C003 C007 1.378(3) . ?
C003 C00M 1.523(7) . ?
C003 C2 1.479(8) . ?
C004 C006 1.385(3) . ?
C004 C007 1.354(3) . ?
C005 C008 1.357(3) . ?
C006 C008 1.374(4) . ?
C006 C00N 1.478(6) . ?
C006 C1 1.531(8) . ?
C009 C00B 1.378(4) . ?
C009 C00F 1.384(4) . ?
C009 C00O 1.526(7) . ?
C009 C00P 1.477(8) . ?
C00A C00C 1.387(3) . ?
C00A C00G 1.373(4) . ?
C00A C00L 1.484(6) . ?
C00A C3 1.550(8) . ?
C00B C00D 1.359(3) . ?
C00C C00J 1.357(3) . ?
C00D C00E 1.359(3) . ?
C00E C00K 1.350(4) . ?
C00F C00K 1.360(4) . ?
C00G C00I 1.359(3) . ?
C00H C00I 1.366(4) . ?
C00H C00J 1.340(4) . ?
C00L C00M 1.309(8) . ?
C00N C00O 1.303(8) . ?
C00P C1 1.339(11) . ?
C2 C3 1.330(11) . ?

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
C005 C003 C00M 136.1(3) . . ?
C005 C003 C2 101.4(4) . . ?
C007 C003 C005 116.8(2) . . ?
C007 C003 C00M 107.1(3) . . ?
C007 C003 C2 141.8(4) . . ?
C007 C004 C006 121.8(2) . . ?
C008 C005 C003 121.5(3) . . ?
C004 C006 C00N 136.0(4) . . ?
C004 C006 C1 103.3(4) . . ?
C008 C006 C004 116.5(2) . . ?
C008 C006 C00N 107.4(3) . . ?
C008 C006 C1 140.2(4) . . ?
C004 C007 C003 121.5(2) . . ?
C005 C008 C006 121.9(2) . . ?
C00B C009 C00F 117.3(3) . . ?
C00B C009 C00O 106.8(3) . . ?
C00B C009 C00P 142.3(4) . . ?
C00F C009 C00O 135.9(4) . . ?
C00F C009 C00P 100.4(4) . . ?
C00C C00A C00L 135.6(4) . . ?
C00C C00A C3 102.7(4) . . ?
C00G C00A C00C 117.3(3) . . ?
C00G C00A C00L 107.0(4) . . ?
C00G C00A C3 140.0(4) . . ?
C00D C00B C009 121.2(2) . . ?
C00J C00C C00A 121.9(3) . . ?
C00B C00D C00E 119.2(3) . . ?
F001 C00E C00D 119.2(3) . . ?
F001 C00E C00K 118.9(3) . . ?
C00K C00E C00D 122.0(3) . . ?
C00K C00F C009 121.9(3) . . ?
C00I C00G C00A 121.4(3) . . ?
F002 C00H C00I 119.5(3) . . ?
C00J C00H F002 118.1(3) . . ?
C00J C00H C00I 122.4(3) . . ?
C00G C00I C00H 118.6(3) . . ?
C00H C00J C00C 118.4(3) . . ?
C00E C00K C00F 118.4(3) . . ?
C00M C00L C00A 121.9(7) . . ?
C00L C00M C003 122.1(7) . . ?
C00O C00N C006 121.9(7) . . ?
C00N C00O C009 121.3(7) . . ?
C1 C00P C009 118.6(9) . . ?
C00P C1 C006 120.6(9) . . ?
C3 C2 C003 118.8(9) . . ?
C2 C3 C00A 120.4(9) . . ?

_olex2_exptl_crystal_mounting_method 'mounted on loop mounter'
_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 1.523
_oxdiff_exptl_absorpt_empirical_full_min 0.734
####################################################################### 
# 
# 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_exp_1177_auto
_database_code_depnum_ccdc_archive 'CCDC 2475425'
loop_
_audit_author_name
_audit_author_address
'Takumi Matsuo'
;Kochi University of Technology
Japan
;
_audit_update_record             
;
2025-07-24 deposited with the CCDC.	2025-11-03 downloaded from the CCDC.
;
_audit_creation_date             2025-07-07
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H16 F2'
_chemical_formula_sum            'C22 H16 F2'
_chemical_formula_weight         318.35
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'

_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.8903(5)
_cell_length_b                   36.587(5)
_cell_length_c                   7.3545(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1585.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3998
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      29.3010
_cell_measurement_theta_min      2.2280
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.961
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.639
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             664
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.0665
0 -1 0 0.0495
-1 -1 0 0.0775
1 1 0 0.1163
0 -1 -1 0.2097
0 1 1 0.1882
-1 2 -2 0.2014
1 1 -2 0.2028

_exptl_crystal_preparation       'mounted using grrease'
_exptl_crystal_recrystallization_method 
'sublimation at 300 deg centigrade for a few minutes in air at RT'
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0001 1.0054 -0.0005 0.0140 -0.0132 0.0029
0.0001 -1.0054 0.0005 -0.0140 0.0132 -0.0029
-1.0012 -1.0086 0.0011 -0.0916 -0.0551 0.0590
1.0012 1.0086 -0.0011 0.0916 0.0551 -0.0590
-0.0003 -1.0073 -0.9998 0.0115 0.0581 0.0786
0.0003 1.0073 0.9998 -0.0115 -0.0581 -0.0786
-1.0025 2.0037 -2.0008 0.0012 -0.0048 0.2307
1.0004 1.0047 -2.0017 0.1425 0.1450 0.1040

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1339
_diffrn_reflns_av_unetI/netI     0.0952
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -45
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            13969
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_min         2.227
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     13.00  38.05   0.15    5.07    --   12.56-117.00  92.00  167
  2  ω     35.00  91.25   0.15    5.07    --   12.56-161.00 -58.00  375
  3  ω    -88.00 -62.95   0.15    5.07    --  -13.19 161.00 -28.00  167
  4  ω    -62.00 -36.95   0.15    5.07    --  -13.19 117.00-179.00  167
  5  ω     51.00  92.25   0.15    5.07    --   12.56 178.00-150.00  275
  6  ω     42.00  67.05   0.15    5.07    --   12.56 178.00 -60.00  167
  7  ω    -72.10   5.00   0.15    5.07    --   12.56 -19.00 150.00  514
  8  ω    -48.00  13.05   0.15    5.07    --  -13.19 -57.00 -30.00  407
  9  ω    -13.00  23.00   0.15    5.07    --  -13.19 -99.00 150.00  240
 10  ω    -88.00 -59.95   0.15    5.07    --  -13.19 -57.00 -30.00  187
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0774795000
_diffrn_orient_matrix_UB_12      0.0138911000
_diffrn_orient_matrix_UB_13      -0.0255163000
_diffrn_orient_matrix_UB_21      0.0681966000
_diffrn_orient_matrix_UB_22      -0.0131276000
_diffrn_orient_matrix_UB_23      -0.0449361000
_diffrn_orient_matrix_UB_31      -0.0618555000
_diffrn_orient_matrix_UB_32      0.0028624000
_diffrn_orient_matrix_UB_33      -0.0814573000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.676
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                1854
_reflns_number_total             3244
_reflns_odcompleteness_completeness 99.85
_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 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.509
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.106
_refine_ls_abs_structure_details 
;
 Flack x determined using 518 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.1(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         3244
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.1672
_refine_ls_R_factor_gt           0.1155
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2966
_refine_ls_wR_factor_ref         0.3346
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C007-C00N \\sim C007-C2
 with sigma of 0.02
 C008-C00L \\sim C008-C1
 with sigma of 0.02
 C007-C00L \\sim C007-C1
 with sigma of 0.04
 C00L-C00N \\sim C1-C2
 with sigma of 0.02
 C008-C00N \\sim C008-C2
 with sigma of 0.04
 C004-C00O \\sim C004-C00P
 with sigma of 0.04
 C004-C00M \\sim C004-C3
 with sigma of 0.02
 C00G-C00O \\sim C00G-C00P
 with sigma of 0.02
 C00M-C00O \\sim C3-C00P
 with sigma of 0.02
 C00G-C00M \\sim C00G-C3
 with sigma of 0.04
3. Others
 Sof(C1)=Sof(H1)=Sof(C2)=Sof(H2)=1-FVAR(1)
 Sof(C00L)=Sof(H00L)=Sof(C00N)=Sof(H00N)=FVAR(1)
 Sof(C3)=Sof(H3)=Sof(C00P)=Sof(H00P)=1-FVAR(2)
 Sof(C00M)=Sof(H00M)=Sof(C00O)=Sof(H00O)=FVAR(2)
4.a Aromatic/amide H refined with riding coordinates:
 C002(H002), C003(H003), C006(H006), C009(H009), C00A(H00A), C00B(H00B),
 C00D(H00D), C00E(H00E), C00F(H00F), C00H(H00H), C00J(H00J), C00K(H00K),
 C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O), C1(H1), C2(H2), C3(H3),
 C00P(H00P)
;
_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 -0.7961(11) -0.27561(14) -0.3133(7) 0.117(2) Uani 1 1 d . . . . .
C002 C -0.2945(9) -0.5020(2) -0.3425(8) 0.0482(16) Uani 1 1 d . . . . .
H002 H -0.149162 -0.503869 -0.287263 0.058 Uiso 1 1 calc R U . . .
C003 C -0.8014(10) -0.33872(19) -0.3535(9) 0.0521(17) Uani 1 1 d . . . . .
H003 H -0.656392 -0.340315 -0.297508 0.063 Uiso 1 1 calc R U . . .
C004 C -0.3942(11) -0.53297(17) -0.4133(8) 0.0477(16) Uani 1 1 d D . . . .
F005 F -0.1972(13) -0.72104(15) -0.5526(8) 0.140(3) Uani 1 1 d . . . . .
C006 C -0.7131(10) -0.4955(2) -0.5028(9) 0.0536(18) Uani 1 1 d . . . . .
H006 H -0.856632 -0.493457 -0.560835 0.064 Uiso 1 1 calc R U . . .
C007 C -0.6113(12) -0.46436(18) -0.4278(9) 0.0533(18) Uani 1 1 d D . . . .
C008 C -0.9074(12) -0.36995(18) -0.4145(9) 0.0540(18) Uani 1 1 d D . . . .
C009 C -0.2006(11) -0.6585(2) -0.5048(10) 0.059(2) Uani 1 1 d . . . . .
H009 H -0.344147 -0.656864 -0.563048 0.070 Uiso 1 1 calc R U . . .
C00A C -0.6079(12) -0.52878(18) -0.4934(9) 0.0521(17) Uani 1 1 d . . . . .
H00A H -0.682096 -0.549601 -0.542693 0.063 Uiso 1 1 calc R U . . .
C00B C -0.3988(11) -0.46898(18) -0.3499(8) 0.0497(17) Uani 1 1 d . . . . .
H00B H -0.323757 -0.448314 -0.299866 0.060 Uiso 1 1 calc R U . . .
C00C C -0.9023(13) -0.30595(19) -0.3726(9) 0.0554(18) Uani 1 1 d . . . . .
C00D C 0.1149(12) -0.6310(2) -0.3565(9) 0.0579(19) Uani 1 1 d . . . . .
H00D H 0.189686 -0.610037 -0.309333 0.069 Uiso 1 1 calc R U . . .
C00E C -1.1128(12) -0.30125(18) -0.4545(9) 0.0542(18) Uani 1 1 d . . . . .
H00E H -1.178612 -0.277762 -0.470332 0.065 Uiso 1 1 calc R U . . .
C00F C 0.2188(11) -0.6642(2) -0.3456(9) 0.0603(19) Uani 1 1 d . . . . .
H00F H 0.365695 -0.665999 -0.292997 0.072 Uiso 1 1 calc R U . . .
C00G C -0.0985(12) -0.62721(19) -0.4353(10) 0.0575(19) Uani 1 1 d D . . . .
C00H C -1.2197(12) -0.3324(2) -0.5109(9) 0.059(2) Uani 1 1 d . . . . .
H00H H -1.366730 -0.330690 -0.563318 0.071 Uiso 1 1 calc R U . . .
C00I C -0.0967(15) -0.69114(19) -0.4898(10) 0.063(2) Uani 1 1 d . . . . .
C00J C -1.1216(12) -0.36582(18) -0.4940(9) 0.0564(18) Uani 1 1 d . . . . .
H00J H -1.199896 -0.386807 -0.536991 0.068 Uiso 1 1 calc R U . . .
C00K C 0.1147(14) -0.6947(2) -0.4090(10) 0.062(2) Uani 1 1 d . . . . .
H00K H 0.185068 -0.717990 -0.398304 0.074 Uiso 1 1 calc R U . . .
C00L C -0.747(2) -0.4012(3) -0.3804(16) 0.041(4) Uani 0.534(18) 1 d D . P A 1
H00L H -0.619657 -0.397724 -0.302889 0.049 Uiso 0.534(18) 1 calc R U P A 1
C00M C -0.2294(17) -0.5637(3) -0.3859(13) 0.041(3) Uani 0.574(17) 1 d D . P B 1
H00M H -0.099336 -0.560235 -0.311530 0.049 Uiso 0.574(17) 1 calc R U P B 1
C00N C -0.7806(19) -0.4340(3) -0.4575(16) 0.040(4) Uani 0.534(18) 1 d D . P A 1
H00N H -0.910879 -0.438038 -0.530899 0.048 Uiso 0.534(18) 1 calc R U P A 1
C00O C -0.2652(18) -0.5964(3) -0.4666(15) 0.043(4) Uani 0.574(17) 1 d D . P B 1
H00O H -0.393947 -0.599985 -0.542358 0.052 Uiso 0.574(17) 1 calc R U P B 1
C1 C -0.864(2) -0.4100(4) -0.436(2) 0.043(4) Uani 0.466(18) 1 d D . P A 2
H1 H -0.983232 -0.425709 -0.474526 0.052 Uiso 0.466(18) 1 calc R U P A 2
C2 C -0.657(2) -0.4241(4) -0.4014(18) 0.045(5) Uani 0.466(18) 1 d D . P A 2
H2 H -0.538778 -0.408514 -0.359902 0.054 Uiso 0.466(18) 1 calc R U P A 2
C3 C -0.348(2) -0.5723(3) -0.443(2) 0.033(4) Uiso 0.426(17) 1 d D . P B 2
H3 H -0.463978 -0.587541 -0.491128 0.039 Uiso 0.426(17) 1 calc R U P B 2
C00P C -0.141(2) -0.5867(4) -0.4030(19) 0.032(4) Uani 0.426(17) 1 d D . P B 2
H00P H -0.024084 -0.571604 -0.355263 0.039 Uiso 0.426(17) 1 calc R U P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F001 C00C 1.347(7) . ?
C002 C004 1.377(9) . ?
C002 C00B 1.358(9) . ?
C003 C008 1.377(9) . ?
C003 C00C 1.345(9) . ?
C004 C00A 1.399(10) . ?
C004 C00M 1.500(12) . ?
C004 C3 1.479(13) . ?
F005 C00I 1.327(7) . ?
C006 C007 1.400(9) . ?
C006 C00A 1.368(9) . ?
C007 C00B 1.387(10) . ?
C007 C00N 1.510(12) . ?
C007 C2 1.511(15) . ?
C008 C00J 1.399(10) . ?
C008 C00L 1.506(13) . ?
C008 C1 1.498(15) . ?
C009 C00G 1.391(10) . ?
C009 C00I 1.346(9) . ?
C00C C00E 1.389(10) . ?
C00D C00F 1.362(9) . ?
C00D C00G 1.391(11) . ?
C00E C00H 1.368(9) . ?
C00F C00K 1.357(10) . ?
C00G C00O 1.513(12) . ?
C00G C00P 1.522(14) . ?
C00H C00J 1.357(9) . ?
C00I C00K 1.386(11) . ?
C00L C00N 1.340(15) . ?
C00M C00O 1.351(14) . ?
C1 C2 1.347(16) . ?
C3 C00P 1.362(16) . ?

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
C00B C002 C004 121.6(6) . . ?
C00C C003 C008 120.3(6) . . ?
C002 C004 C00A 116.9(6) . . ?
C002 C004 C00M 106.9(6) . . ?
C002 C004 C3 141.0(8) . . ?
C00A C004 C00M 136.2(7) . . ?
C00A C004 C3 102.1(7) . . ?
C00A C006 C007 120.7(6) . . ?
C006 C007 C00N 105.0(7) . . ?
C006 C007 C2 140.1(8) . . ?
C00B C007 C006 116.8(6) . . ?
C00B C007 C00N 138.2(8) . . ?
C00B C007 C2 103.1(8) . . ?
C003 C008 C00J 117.1(6) . . ?
C003 C008 C00L 107.0(8) . . ?
C003 C008 C1 140.3(8) . . ?
C00J C008 C00L 135.9(8) . . ?
C00J C008 C1 102.5(8) . . ?
C00I C009 C00G 120.3(7) . . ?
C006 C00A C004 121.8(6) . . ?
C002 C00B C007 122.2(6) . . ?
F001 C00C C00E 116.9(7) . . ?
C003 C00C F001 119.7(7) . . ?
C003 C00C C00E 123.4(6) . . ?
C00F C00D C00G 121.3(6) . . ?
C00H C00E C00C 116.0(6) . . ?
C00K C00F C00D 120.7(7) . . ?
C009 C00G C00D 117.5(6) . . ?
C009 C00G C00O 106.1(7) . . ?
C009 C00G C00P 142.0(8) . . ?
C00D C00G C00O 136.4(8) . . ?
C00D C00G C00P 100.4(8) . . ?
C00J C00H C00E 121.8(7) . . ?
F005 C00I C009 120.0(8) . . ?
F005 C00I C00K 118.1(7) . . ?
C009 C00I C00K 121.8(6) . . ?
C00H C00J C008 121.3(6) . . ?
C00F C00K C00I 118.4(6) . . ?
C00N C00L C008 121.0(12) . . ?
C00O C00M C004 120.2(9) . . ?
C00L C00N C007 119.9(11) . . ?
C00M C00O C00G 119.4(10) . . ?
C2 C1 C008 120.5(13) . . ?
C1 C2 C007 120.6(13) . . ?
C00P C3 C004 120.6(13) . . ?
C3 C00P C00G 119.4(12) . . ?

_olex2_exptl_crystal_mounting_method 'mounted on loop mounter'
_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 2.744
_oxdiff_exptl_absorpt_empirical_full_min 0.505
####################################################################### 
# 
# 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_exp_1054
_database_code_depnum_ccdc_archive 'CCDC 2475424'
loop_
_audit_author_name
_audit_author_address
'Takumi Matsuo'
;Kochi University of Technology
Japan
;
_audit_update_record             
;
2025-07-24 deposited with the CCDC.	2025-11-03 downloaded from the CCDC.
;
_audit_creation_date             2025-05-03
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H16 F2'
_chemical_formula_sum            'C22 H16 F2'
_chemical_formula_weight         318.35
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'

_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/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   16.0429(11)
_cell_length_b                   3.9191(2)
_cell_length_c                   13.1309(8)
_cell_angle_alpha                90
_cell_angle_beta                 111.325(7)
_cell_angle_gamma                90
_cell_volume                     769.06(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2618
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      29.6950
_cell_measurement_theta_min      3.0920
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.882
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.767
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             332
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.1181
0 0 1 0.1259
-1 0 0 0.0226
1 0 0 0.0376
-2 1 -1 0.4761
2 -1 1 0.5403

_exptl_crystal_preparation       'mounted using grease'
_exptl_crystal_recrystallization_method 'in soln phase'
_exptl_crystal_size_max          0.85
_exptl_crystal_size_mid          0.286
_exptl_crystal_size_min          0.06
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0003 -0.0001 -1.0000 0.0264 -0.0129 0.0500
0.0003 0.0001 1.0000 -0.0264 0.0129 -0.0500
-1.0002 0.0002 -0.0015 0.0447 0.0160 0.0007
1.0002 -0.0002 0.0015 -0.0447 -0.0160 -0.0007
-2.0013 1.0006 -1.0007 0.0588 0.1759 0.1219
2.0013 -1.0006 1.0007 -0.0588 -0.1759 -0.1219

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5586
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.364
_diffrn_reflns_theta_min         2.726
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -37.00  37.00   0.50   10.15    --   12.72 -92.00-126.00  148
  2  ω    -40.00  14.00   0.50   10.15    --  -13.34 -92.00-126.00  108
  3  ω    -58.00 -32.00   0.50   10.15    --   12.72 -19.00-180.00   52
  4  ω    -54.00  41.00   0.50   10.15    --  -13.34  92.00 -13.00  190
  5  ω     42.00  92.00   0.50   10.15    --   12.72 178.00-150.00  100
  6  ω     -6.00  28.00   0.50   10.15    --  -13.34 -99.00  60.00   68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0446622000
_diffrn_orient_matrix_UB_12      -0.0569355000
_diffrn_orient_matrix_UB_13      -0.0264015000
_diffrn_orient_matrix_UB_21      -0.0160347000
_diffrn_orient_matrix_UB_22      0.1566041000
_diffrn_orient_matrix_UB_23      0.0129016000
_diffrn_orient_matrix_UB_31      -0.0005627000
_diffrn_orient_matrix_UB_32      0.0706596000
_diffrn_orient_matrix_UB_33      -0.0499921000
_diffrn_oxdiff_digest_frames     
;
011096fc6848fa36cf304015ae6d44751b006665e1f
;
_diffrn_oxdiff_digest_hkl        
;
01070007f70e22663958eec4cc61f7fe85be9f
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1262
_reflns_number_total             1560
_reflns_odcompleteness_completeness 99.78
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1560
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0410
_refine_ls_restrained_S_all      1.067
_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)+(0.0581P)²+0.2178P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1088
_refine_ls_wR_factor_ref         0.1181
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C004(H004), C005(H005), C006(H006), C008(H008), C009(H009), C00A(H00A),
 C00B(H00B), C00C(H00C)
;
_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 0.11662(6) 0.1835(2) 0.48391(7) 0.0379(3) Uani 1 1 d . . . . .
C002 C 0.22699(9) 0.4623(3) 0.63119(11) 0.0258(3) Uani 1 1 d . . . . .
C003 C 0.14051(10) 0.3339(4) 0.58415(11) 0.0275(3) Uani 1 1 d . . . . .
C004 C 0.29040(9) 0.4287(3) 0.57493(11) 0.0268(3) Uani 1 1 d . . . . .
H004 H 0.272113 0.292778 0.510630 0.032 Uiso 1 1 calc R . . . .
C005 C 0.37173(9) 0.5713(3) 0.60547(11) 0.0267(3) Uani 1 1 d . . . . .
H005 H 0.389530 0.710890 0.668940 0.032 Uiso 1 1 calc R . . . .
C006 C 0.52300(9) 0.6581(3) 0.60032(11) 0.0275(3) Uani 1 1 d . . . . .
H006 H 0.539422 0.767359 0.669425 0.033 Uiso 1 1 calc R . . . .
C007 C 0.43574(9) 0.5325(3) 0.55047(11) 0.0255(3) Uani 1 1 d . . . . .
C008 C 0.18640(10) 0.6302(4) 0.78516(12) 0.0319(4) Uani 1 1 d . . . . .
H008 H 0.202562 0.732728 0.855276 0.038 Uiso 1 1 calc R . . . .
C009 C 0.24781(10) 0.6152(3) 0.73405(12) 0.0285(3) Uani 1 1 d . . . . .
H009 H 0.305608 0.710662 0.769439 0.034 Uiso 1 1 calc R . . . .
C00A C 0.58577(9) 0.6269(3) 0.55149(11) 0.0273(3) Uani 1 1 d . . . . .
H00A H 0.644358 0.714767 0.587534 0.033 Uiso 1 1 calc R . . . .
C00B C 0.10116(10) 0.4964(4) 0.73457(12) 0.0321(4) Uani 1 1 d . . . . .
H00B H 0.059086 0.506936 0.770022 0.038 Uiso 1 1 calc R . . . .
C00C C 0.07755(10) 0.3473(4) 0.63228(12) 0.0301(3) Uani 1 1 d . . . . .
H00C H 0.019264 0.256652 0.596317 0.036 Uiso 1 1 calc R . . . .


_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 C003 1.3636(16) . ?
C002 C003 1.392(2) . ?
C002 C004 1.464(2) . ?
C002 C009 1.402(2) . ?
C003 C00C 1.374(2) . ?
C004 C005 1.340(2) . ?
C005 C007 1.462(2) . ?
C006 C007 1.4014(19) . ?
C006 C00A 1.382(2) . ?
C007 C00A 1.4021(19) 3_666 ?
C008 C009 1.380(2) . ?
C008 C00B 1.388(2) . ?
C00B C00C 1.385(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
C003 C002 C004 120.45(13) . . ?
C003 C002 C009 115.58(13) . . ?
C009 C002 C004 123.95(13) . . ?
F001 C003 C002 118.01(12) . . ?
F001 C003 C00C 117.72(12) . . ?
C00C C003 C002 124.27(13) . . ?
C005 C004 C002 126.23(13) . . ?
C004 C005 C007 126.25(13) . . ?
C00A C006 C007 121.67(13) . . ?
C006 C007 C005 119.64(13) . . ?
C006 C007 C00A 117.36(13) . 3_666 ?
C00A C007 C005 123.00(13) 3_666 . ?
C009 C008 C00B 120.29(14) . . ?
C008 C009 C002 121.64(13) . . ?
C006 C00A C007 120.97(13) . 3_666 ?
C00C C00B C008 119.86(13) . . ?
C003 C00C C00B 118.35(13) . . ?

_olex2_exptl_crystal_mounting_method 'mounted on loop mounter'
_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 1.706
_oxdiff_exptl_absorpt_empirical_full_min 0.747
