# Supplementary Information (SI) for Journal of Materials Chemistry C.
# 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_212
_audit_block_doi                 10.5517/ccdc.csd.cc2m7h8n
_database_code_depnum_ccdc_archive 'CCDC 2420271'
loop_
_audit_author_name
_audit_author_address
'Takumi Matsuo'
;Kochi University of Technology
Japan
;
_audit_update_record             
;
2025-01-29 deposited with the CCDC.	2025-04-14 downloaded from the CCDC.
;
_audit_creation_date             2023-12-13
_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 H10 F4 O2'
_chemical_formula_sum            'C22 H10 F4 O2'
_chemical_formula_weight         382.30
_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'
O O 0.0106 0.0060 '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                   17.3791(19)
_cell_length_b                   4.6272(4)
_cell_length_c                   19.4665(17)
_cell_angle_alpha                90
_cell_angle_beta                 98.682(9)
_cell_angle_gamma                90
_cell_volume                     1547.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3174
_cell_measurement_temperature    103.15
_cell_measurement_theta_max      30.0850
_cell_measurement_theta_min      2.3810
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.673
_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 yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.641
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             776
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 0 0.0993
1 0 0 0.0248
0 0 -1 0.0395
0 0 1 0.0734
0 -1 0 0.3857
0 1 0 0.4237

_exptl_crystal_preparation       'in soln'
_exptl_crystal_recrystallization_method 'in soln'
_exptl_crystal_size_max          0.812
_exptl_crystal_size_mid          0.142
_exptl_crystal_size_min          0.113
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
-1.0013 -0.0010 -0.0006 0.0297 -0.0281 -0.0064
1.0013 0.0010 0.0006 -0.0297 0.0281 0.0064
0.0014 0.0015 -1.0024 0.0292 0.0226 0.0012
-0.0014 -0.0015 1.0024 -0.0292 -0.0226 -0.0012
0.0494 -0.9909 -0.0744 0.0113 -0.0204 0.1501
-0.0494 0.9909 0.0744 -0.0113 0.0204 -0.1501

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            4709
_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         26.368
_diffrn_reflns_theta_min         2.117
_diffrn_ambient_temperature      103.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_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    -32.00  56.00   0.50   12.93    --  -13.34   9.00-145.00  176
  2  ω    -20.00  32.00   0.50   12.93    --  -13.34 -99.00-180.00  104
  3  ω    -43.00   0.00   0.50   12.93    --   12.72 -19.00-180.00   86
  4  ω    -98.00 -29.00   0.50   12.93    --  -13.34  -9.00  40.00  138
  5  ω     65.00  95.00   0.50   12.93    --   12.72 178.00 -90.00   60
;
_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      -0.0296195000
_diffrn_orient_matrix_UB_12      -0.0106967000
_diffrn_orient_matrix_UB_13      -0.0291873000
_diffrn_orient_matrix_UB_21      0.0280280000
_diffrn_orient_matrix_UB_22      0.0236707000
_diffrn_orient_matrix_UB_23      -0.0224321000
_diffrn_orient_matrix_UB_31      0.0064995000
_diffrn_orient_matrix_UB_32      -0.1510712000
_diffrn_orient_matrix_UB_33      -0.0014482000
_diffrn_oxdiff_digest_frames     
;
01981220331405d01deab174ca17ed7f5d005644077
;
_diffrn_oxdiff_digest_hkl        
;
01b6f45ddee736d4379c1a039ac53c7402f68d
;
_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                1328
_reflns_number_total             1580
_reflns_odcompleteness_completeness 99.55
_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         0.397
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1580
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0496
_refine_ls_restrained_S_all      1.119
_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)+(0.0893P)²+0.5400P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1346
_refine_ls_wR_factor_ref         0.1445
_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:
 C006(H006), C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E)
;
_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 0.34782(6) 0.1379(2) 0.46308(5) 0.0228(3) Uani 1 1 d . . . . .
F002 F 0.41183(6) -0.2262(2) 0.38644(5) 0.0242(3) Uani 1 1 d . . . . .
O003 O 0.36418(7) 0.5493(3) 0.55809(6) 0.0177(3) Uani 1 1 d . . . . .
C004 C 0.34451(11) 0.7270(4) 0.60990(8) 0.0156(4) Uani 1 1 d . . . . .
C005 C 0.45772(11) -0.1148(4) 0.44206(9) 0.0158(4) Uani 1 1 d . . . . .
C006 C 0.45424(11) 0.4890(4) 0.65387(9) 0.0171(4) Uani 1 1 d . . . . .
H006 H 0.498617 0.421083 0.684086 0.020 Uiso 1 1 calc R . . . .
C007 C 0.42372(10) 0.0797(4) 0.48260(9) 0.0163(4) Uani 1 1 d . . . . .
C008 C 0.39826(11) 0.6978(4) 0.67032(9) 0.0164(4) Uani 1 1 d . . . . .
C009 C 0.46472(10) 0.2033(4) 0.54257(8) 0.0151(4) Uani 1 1 d . . . . .
C00A C 0.43137(10) 0.4081(4) 0.58703(8) 0.0155(4) Uani 1 1 d . . . . .
C00B C 0.32401(12) 1.0447(4) 0.72382(9) 0.0199(4) Uani 1 1 d . . . . .
H00B H 0.315797 1.156758 0.762967 0.024 Uiso 1 1 calc R . . . .
C00C C 0.38767(11) 0.8608(4) 0.72923(9) 0.0193(4) Uani 1 1 d . . . . .
H00C H 0.422991 0.845221 0.771358 0.023 Uiso 1 1 calc R . . . .
C00D C 0.27166(11) 1.0691(4) 0.66209(9) 0.0210(4) Uani 1 1 d . . . . .
H00D H 0.228830 1.197880 0.660237 0.025 Uiso 1 1 calc R . . . .
C00E C 0.28074(11) 0.9092(4) 0.60330(9) 0.0193(4) Uani 1 1 d . . . . .
H00E H 0.245320 0.924394 0.561219 0.023 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 C007 1.344(2) . ?
F002 C005 1.347(2) . ?
O003 C004 1.3834(19) . ?
O003 C00A 1.382(2) . ?
C004 C008 1.394(2) . ?
C004 C00E 1.383(3) . ?
C005 C007 1.387(2) . ?
C005 C009 1.397(3) 5_656 ?
C006 C008 1.441(2) . ?
C006 C00A 1.355(2) . ?
C007 C009 1.395(2) . ?
C008 C00C 1.408(2) . ?
C009 C00A 1.461(2) . ?
C00B C00C 1.387(3) . ?
C00B C00D 1.398(3) . ?
C00D C00E 1.391(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00A O003 C004 105.69(13) . . ?
O003 C004 C008 110.47(15) . . ?
C00E C004 O003 125.27(16) . . ?
C00E C004 C008 124.26(15) . . ?
F002 C005 C007 117.03(16) . . ?
F002 C005 C009 119.68(15) . 5_656 ?
C007 C005 C009 123.27(16) . 5_656 ?
C00A C006 C008 106.77(16) . . ?
F001 C007 C005 116.97(15) . . ?
F001 C007 C009 120.67(15) . . ?
C005 C007 C009 122.32(17) . . ?
C004 C008 C006 105.45(14) . . ?
C004 C008 C00C 118.84(16) . . ?
C00C C008 C006 135.71(17) . . ?
C005 C009 C00A 121.29(16) 5_656 . ?
C007 C009 C005 114.42(15) . 5_656 ?
C007 C009 C00A 124.29(16) . . ?
O003 C00A C009 116.84(14) . . ?
C006 C00A O003 111.62(15) . . ?
C006 C00A C009 131.54(17) . . ?
C00C C00B C00D 121.51(16) . . ?
C00B C00C C008 117.88(17) . . ?
C00E C00D C00B 121.63(17) . . ?
C004 C00E C00D 115.88(17) . . ?


_olex2_exptl_crystal_mounting_method loop
_olex2_submission_original_sample_id -
_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 3.133
_oxdiff_exptl_absorpt_empirical_full_min 0.348
####################################################################### 
# 
# 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_230
_audit_block_doi                 10.5517/ccdc.csd.cc2m7hcr
_database_code_depnum_ccdc_archive 'CCDC 2420274'
loop_
_audit_author_name
_audit_author_address
'Takumi Matsuo'
;Kochi University of Technology
Japan
;
_audit_update_record             
;
2025-01-29 deposited with the CCDC.	2025-04-14 downloaded from the CCDC.
;
_audit_creation_date             2023-12-27
_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 H6.11 F4 S2'
_chemical_formula_sum            'C22 H10 F4 S2'
_chemical_formula_weight         414.42
_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'
S S 0.1246 0.1234 '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                   6.7329(6)
_cell_length_b                   6.3925(5)
_cell_length_c                   20.818(2)
_cell_angle_alpha                90
_cell_angle_beta                 112.145(12)
_cell_angle_gamma                90
_cell_volume                     829.93(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2763
_cell_measurement_temperature    103.15
_cell_measurement_theta_max      29.5500
_cell_measurement_theta_min      2.1290
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.369
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.666
_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    1.658
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             420
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 1 0.0601
0 1 0 0.3387
0 -1 0 0.3894
0 0 -1 0.0591
1 0 -1 0.0245
0 0 1 0.0192

_exptl_crystal_preparation       'mounted using grease'
_exptl_crystal_recrystallization_method 'in soln'
_exptl_crystal_size_max          0.728
_exptl_crystal_size_mid          0.085
_exptl_crystal_size_min          0.078
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
-1.0007 0.0002 1.0032 -0.0269 0.0269 0.0985
0.0008 1.0008 0.0002 -0.0111 0.1059 -0.0319
-0.0008 -1.0008 -0.0002 0.0111 -0.1059 0.0319
0.0001 -0.0001 -0.9997 -0.0358 -0.0056 -0.0060
1.0007 -0.0002 -1.0032 0.0269 -0.0269 -0.0985
-0.0001 0.0001 0.9997 0.0358 0.0056 0.0060

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            5673
_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         26.369
_diffrn_reflns_theta_min         2.112
_diffrn_ambient_temperature      103.15
_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     21.00  59.00   0.50   23.59    --   12.72-102.00  44.00   76
  2  ω    -72.00 -19.00   0.50   23.59    --   12.72 -19.00-180.00  106
  3  ω     48.00  95.00   0.50   23.59    --   12.72 178.00 -30.00   94
  4  ω     43.00  95.00   0.50   23.59    --   12.72 178.00   0.00  104
  5  ω     42.00  88.00   0.50   23.59    --   12.72 178.00  90.00   92
  6  ω    -20.00  13.00   0.50   23.59    --   12.72 102.00 147.00   66
  7  ω    -43.00 -17.00   0.50   23.59    --  -13.34 102.00 147.00   52
  8  ω    -73.00 -42.00   0.50   23.59    --  -13.34-178.00 150.00   62
;
_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      0.0628038000
_diffrn_orient_matrix_UB_12      -0.0111229000
_diffrn_orient_matrix_UB_13      0.0358297000
_diffrn_orient_matrix_UB_21      -0.0212452000
_diffrn_orient_matrix_UB_22      0.1058281000
_diffrn_orient_matrix_UB_23      0.0055783000
_diffrn_orient_matrix_UB_31      -0.0923658000
_diffrn_orient_matrix_UB_32      -0.0318167000
_diffrn_orient_matrix_UB_33      0.0060316000
_diffrn_oxdiff_digest_frames     
;
0184078ab9b7ba920cd016bcf141976ea600652ad49
;
_diffrn_oxdiff_digest_hkl        
;
017d27c3ac37c75a8ce080cd2f65ff0c2bb392
;
_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                1354
_reflns_number_total             1690
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         1690
_refine_ls_number_restraints     22
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0521
_refine_ls_restrained_S_all      1.113
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0492P)²+1.0956P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1281
_refine_ls_wR_factor_ref         0.1357
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 S5-C2 \\sim S5A-C2
 with sigma of 0.02
 S5-C8 \\sim S5A-C8A
 with sigma of 0.02
 C1-C2 \\sim C1A-C2
 with sigma of 0.02
 C1-C7 \\sim C1A-C7A
 with sigma of 0.02
 C4-C7 \\sim C4A-C7A
 with sigma of 0.02
 C4-C \\sim C4A-CA
 with sigma of 0.02
 C6-C8 \\sim C6A-C8A
 with sigma of 0.02
 C6-C9 \\sim C6A-C9A
 with sigma of 0.02
 C7-C8 \\sim C7A-C8A
 with sigma of 0.02
 C9-C \\sim C9A-CA
 with sigma of 0.02
 S5-C6 \\sim S5A-C6A
 with sigma of 0.04
 S5-C7 \\sim S5A-C7A
 with sigma of 0.04
 C1-C4 \\sim C1A-C4A
 with sigma of 0.04
 C1-C8 \\sim C1A-C8A
 with sigma of 0.04
 C2-C7 \\sim C2-C7A
 with sigma of 0.04
 C2-C8 \\sim C2-C8A
 with sigma of 0.04
 C4-C8 \\sim C4A-C8A
 with sigma of 0.04
 C4-C9 \\sim C4A-C9A
 with sigma of 0.04
 C6-C7 \\sim C6A-C7A
 with sigma of 0.04
 C6-C \\sim C6A-CA
 with sigma of 0.04
 C7-C \\sim C7A-CA
 with sigma of 0.04
 C8-C9 \\sim C8A-C9A
 with sigma of 0.04
3. Others
 Sof(S5A)=Sof(C1A)=Sof(C7A)=Sof(C8A)=Sof(C6A)=Sof(C9A)=Sof(CA)=Sof(C4A)=1-
 FVAR(1)
 Sof(S5)=Sof(C1)=Sof(H1)=Sof(C4)=Sof(H4)=Sof(C6)=Sof(H6)=Sof(C7)=Sof(C8)=
 Sof(C9)=Sof(H9)=Sof(C)=Sof(H)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C6(H6), C9(H9), C(H)
;
_atom_sites_solution_hydrogens   geom
_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
S5 S 0.2863(3) 0.00609(18) 0.12850(6) 0.0237(4) Uani 0.611(3) 1 d D . P A 1
C1 C -0.1264(11) -0.0046(8) 0.0858(3) 0.0268(11) Uani 0.611(3) 1 d D . P A 1
H1 H -0.271199 0.026862 0.063663 0.032 Uiso 0.611(3) 1 calc R . P A 1
F F 0.3669(2) 0.6911(3) 0.00982(9) 0.0361(5) Uani 1 1 d . . . . .
F1 F 0.3899(2) 0.3539(3) 0.08038(9) 0.0340(5) Uani 1 1 d . . . . .
C10 C 0.0136(4) 0.3087(4) 0.03958(13) 0.0192(6) Uani 1 1 d . . . . .
C2 C 0.0265(4) 0.1151(4) 0.07924(13) 0.0207(6) Uani 1 1 d D . . . .
C3 C 0.1916(4) 0.4212(4) 0.04056(14) 0.0222(6) Uani 1 1 d . . . . .
C4 C -0.1798(18) -0.3413(18) 0.1445(6) 0.026(3) Uani 0.611(3) 1 d D . P A 1
H4 H -0.328843 -0.336356 0.126232 0.031 Uiso 0.611(3) 1 calc R . P A 1
C5 C 0.1795(4) 0.6005(4) 0.00316(14) 0.0227(6) Uani 1 1 d . . . . .
C6 C 0.2743(18) -0.3629(19) 0.1985(7) 0.026(2) Uani 0.611(3) 1 d D . P A 1
H6 H 0.423016 -0.372193 0.215263 0.031 Uiso 0.611(3) 1 calc R . P A 1
C7 C -0.0557(17) -0.1805(17) 0.1281(6) 0.023(2) Uani 0.611(3) 1 d D . P A 1
C8 C 0.1693(17) -0.199(2) 0.1570(7) 0.023(2) Uani 0.611(3) 1 d D . P A 1
C9 C 0.1530(15) -0.5146(16) 0.2149(6) 0.027(2) Uani 0.611(3) 1 d D . P A 1
H9 H 0.221359 -0.624963 0.243937 0.032 Uiso 0.611(3) 1 calc R . P A 1
C C -0.0726(16) -0.5025(16) 0.1879(5) 0.026(2) Uani 0.611(3) 1 d D . P A 1
H H -0.150938 -0.605293 0.199482 0.031 Uiso 0.611(3) 1 calc R . P A 1
S5A S -0.2211(4) -0.0067(3) 0.07394(11) 0.0187(6) Uiso 0.389(3) 1 d D . P A 2
C1A C 0.1918(16) 0.0115(12) 0.1204(4) 0.020(2) Uiso 0.389(3) 1 d D . P A 2
C7A C 0.144(3) -0.174(3) 0.1487(12) 0.018(4) Uiso 0.389(3) 1 d D . P A 2
C8A C -0.079(3) -0.210(3) 0.1296(10) 0.013(3) Uiso 0.389(3) 1 d D . P A 2
C6A C -0.160(3) -0.376(3) 0.1525(11) 0.019(4) Uiso 0.389(3) 1 d D . P A 2
C9A C -0.022(3) -0.517(3) 0.1971(10) 0.022(4) Uiso 0.389(3) 1 d D . P A 2
CA C 0.197(3) -0.485(3) 0.2187(11) 0.026(4) Uiso 0.389(3) 1 d D . P A 2
C4A C 0.285(3) -0.319(3) 0.1971(13) 0.029(5) Uiso 0.389(3) 1 d D . 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
S5 C2 1.801(3) . ?
S5 C8 1.746(11) . ?
C1 C2 1.330(7) . ?
C1 C7 1.397(11) . ?
F C5 1.347(3) . ?
F1 C3 1.349(3) . ?
C10 C2 1.472(4) . ?
C10 C3 1.391(4) . ?
C10 C5 1.395(4) 3_565 ?
C2 S5A 1.805(3) . ?
C2 C1A 1.301(9) . ?
C3 C5 1.371(4) . ?
C4 C7 1.444(13) . ?
C4 C 1.381(13) . ?
C6 C8 1.371(14) . ?
C6 C9 1.391(14) . ?
C7 C8 1.408(9) . ?
C9 C 1.409(10) . ?
S5A C8A 1.762(15) . ?
C1A C7A 1.413(17) . ?
C7A C8A 1.418(12) . ?
C7A C4A 1.434(19) . ?
C8A C6A 1.362(19) . ?
C6A C9A 1.374(17) . ?
C9A CA 1.387(13) . ?
CA C4A 1.369(18) . ?

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
C8 S5 C2 91.1(4) . . ?
C2 C1 C7 115.8(6) . . ?
C3 C10 C2 123.9(2) . . ?
C3 C10 C5 112.6(2) . 3_565 ?
C5 C10 C2 123.4(2) 3_565 . ?
C1 C2 S5 110.0(3) . . ?
C1 C2 C10 131.1(3) . . ?
C10 C2 S5 118.94(18) . . ?
C10 C2 S5A 118.08(19) . . ?
C1A C2 C10 130.7(4) . . ?
C1A C2 S5A 111.2(4) . . ?
F1 C3 C10 119.5(2) . . ?
F1 C3 C5 116.7(2) . . ?
C5 C3 C10 123.9(2) . . ?
C C4 C7 118.6(10) . . ?
F C5 C10 119.9(2) . 3_565 ?
F C5 C3 116.6(2) . . ?
C3 C5 C10 123.5(2) . 3_565 ?
C8 C6 C9 118.4(10) . . ?
C1 C7 C4 129.2(9) . . ?
C1 C7 C8 113.2(9) . . ?
C8 C7 C4 117.6(12) . . ?
C6 C8 S5 126.6(9) . . ?
C6 C8 C7 123.3(12) . . ?
C7 C8 S5 110.0(9) . . ?
C6 C9 C 120.5(10) . . ?
C4 C C9 121.4(10) . . ?
C8A S5A C2 91.0(5) . . ?
C2 C1A C7A 115.4(10) . . ?
C1A C7A C8A 113.7(14) . . ?
C1A C7A C4A 129.9(16) . . ?
C8A C7A C4A 116.2(18) . . ?
C7A C8A S5A 108.7(12) . . ?
C6A C8A S5A 127.8(13) . . ?
C6A C8A C7A 123.5(17) . . ?
C8A C6A C9A 119.2(16) . . ?
C6A C9A CA 119.4(19) . . ?
C4A CA C9A 123(2) . . ?
CA C4A C7A 118.8(18) . . ?


_olex2_exptl_crystal_mounting_method loop
_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 2.035
_oxdiff_exptl_absorpt_empirical_full_min 0.738
####################################################################### 
# 
# 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_939
_audit_block_doi                 10.5517/ccdc.csd.cc2m7hgv
_database_code_depnum_ccdc_archive 'CCDC 2420277'
loop_
_audit_author_name
_audit_author_address
'Takumi Matsuo'
;Kochi University of Technology
Japan
;
_audit_update_record             
;
2025-01-29 deposited with the CCDC.	2025-04-14 downloaded from the CCDC.
;
_audit_creation_date             2025-01-21
_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 H14 F4'
_chemical_formula_sum            'C22 H14 F4'
_chemical_formula_weight         354.33
_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                   7.8022(7)
_cell_length_b                   5.7869(4)
_cell_length_c                   18.0999(17)
_cell_angle_alpha                90
_cell_angle_beta                 96.941(8)
_cell_angle_gamma                90
_cell_volume                     811.23(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1596
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      28.8570
_cell_measurement_theta_min      3.6970
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.802
_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 colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             364
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 1 0.1265
-1 0 0 0.1333
1 0 0 0.1214
0 -1 1 0.2824
0 1 -1 0.2901
0 0 1 0.0535
0 0 -1 0.0572

_exptl_crystal_preparation       'mounted using grease'
_exptl_crystal_recrystallization_method 'vapor diffusion (soln process)'
_exptl_crystal_size_max          0.637
_exptl_crystal_size_mid          0.263
_exptl_crystal_size_min          0.09
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
-0.9987 -0.0004 1.0005 -0.0203 0.0859 0.0356
-0.9986 -0.0003 0.0017 -0.0545 0.0677 0.0285
0.9986 0.0003 -0.0017 0.0545 -0.0677 -0.0285
-0.0010 -0.9996 0.9984 0.0353 -0.0287 0.1203
0.0010 0.9996 -0.9984 -0.0353 0.0287 -0.1203
-0.0001 -0.0001 0.9987 0.0342 0.0182 0.0071
0.0001 0.0001 -0.9987 -0.0342 -0.0182 -0.0071

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_unetI/netI     0.0519
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            4531
_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         26.371
_diffrn_reflns_theta_min         2.267
_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    -19.00  28.00   0.50   17.86    --  -13.34 -99.00 -90.00   94
  2  ω    -93.00  -4.00   0.50   17.86    --  -13.34 -30.00  10.00  178
  3  ω    -28.00  25.00   0.50   17.86    --  -13.34  30.00 171.00  106
  4  ω     31.00  69.00   0.50   17.86    --  -13.34  30.00 171.00   76
  5  ω     61.00  88.00   0.50   17.86    --   12.72 178.00 -60.00   54
;
_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      0.0546493000
_diffrn_orient_matrix_UB_12      -0.0011607000
_diffrn_orient_matrix_UB_13      0.0342915000
_diffrn_orient_matrix_UB_21      -0.0677548000
_diffrn_orient_matrix_UB_22      0.0469452000
_diffrn_orient_matrix_UB_23      0.0181972000
_diffrn_orient_matrix_UB_31      -0.0284726000
_diffrn_orient_matrix_UB_32      -0.1132452000
_diffrn_orient_matrix_UB_33      0.0071239000
_diffrn_oxdiff_digest_frames     
;
01462befe106a42c01b6cba0f3ec3c471d0050873fc
;
_diffrn_oxdiff_digest_hkl        
;
0114ee66b271edee1254bf3d8fea2a66134365
;
_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                1160
_reflns_number_total             1663
_reflns_odcompleteness_completeness 99.95
_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         0.518
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1663
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1128
_refine_ls_R_factor_gt           0.0846
_refine_ls_restrained_S_all      1.084
_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)+(0.1542P)²+0.8875P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2576
_refine_ls_wR_factor_ref         0.2810
_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:
 C006(H006), C008(H008), C009(H009), C00A(H00A), C00B(H00B), C00C(H00C),
 C00D(H00D)
;
_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 1.2011(3) 0.8757(4) 0.53032(12) 0.0458(7) Uani 1 1 d . . . . .
F002 F 0.9218(3) 0.8314(4) 0.59559(12) 0.0468(7) Uani 1 1 d . . . . .
C003 C 0.9567(5) 0.6638(6) 0.54799(19) 0.0362(9) Uani 1 1 d . . . . .
C004 C 1.1020(5) 0.6870(6) 0.51386(19) 0.0358(9) Uani 1 1 d . . . . .
C005 C 0.8465(4) 0.4755(6) 0.53550(19) 0.0359(9) Uani 1 1 d . . . . .
C006 C 0.3998(5) 0.6737(6) 0.6953(2) 0.0399(9) Uani 1 1 d . . . . .
H006 H 0.463265 0.813107 0.704059 0.048 Uiso 1 1 calc R . . . .
C007 C 0.4515(5) 0.5135(7) 0.6459(2) 0.0404(9) Uani 1 1 d . . . . .
C008 C 0.2595(5) 0.6349(7) 0.7315(2) 0.0420(10) Uani 1 1 d . . . . .
H008 H 0.226998 0.746749 0.765600 0.050 Uiso 1 1 calc R . . . .
C009 C 0.3544(5) 0.3142(7) 0.6322(2) 0.0414(10) Uani 1 1 d . . . . .
H009 H 0.386318 0.203895 0.597502 0.050 Uiso 1 1 calc R . . . .
C00A C 0.2109(5) 0.2743(6) 0.6689(2) 0.0419(10) Uani 1 1 d . . . . .
H00A H 0.145194 0.137006 0.659497 0.050 Uiso 1 1 calc R . . . .
C00B C 0.1641(5) 0.4351(7) 0.7192(2) 0.0425(10) Uani 1 1 d . . . . .
H00B H 0.066993 0.408326 0.745043 0.051 Uiso 1 1 calc R . . . .
C00C C 0.6888(5) 0.4310(7) 0.5696(2) 0.0429(10) Uani 1 1 d . . . . .
H00C H 0.635997 0.284657 0.559490 0.051 Uiso 1 1 calc R . . . .
C00D C 0.6118(5) 0.5700(7) 0.6126(2) 0.0433(10) Uani 1 1 d . . . . .
H00D H 0.662221 0.717596 0.623226 0.052 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 C004 1.351(4) . ?
F002 C003 1.346(4) . ?
C003 C004 1.362(5) . ?
C003 C005 1.390(5) . ?
C004 C005 1.390(5) 3_766 ?
C005 C00C 1.465(5) . ?
C006 C007 1.380(5) . ?
C006 C008 1.361(6) . ?
C007 C009 1.386(6) . ?
C007 C00D 1.490(6) . ?
C008 C00B 1.379(6) . ?
C009 C00A 1.388(6) . ?
C00A C00B 1.381(6) . ?
C00C C00D 1.314(6) . ?

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
F002 C003 C004 117.6(3) . . ?
F002 C003 C005 120.0(3) . . ?
C004 C003 C005 122.4(3) . . ?
F001 C004 C003 117.8(3) . . ?
F001 C004 C005 119.1(3) . 3_766 ?
C003 C004 C005 123.1(3) . 3_766 ?
C003 C005 C004 114.5(3) . 3_766 ?
C003 C005 C00C 127.2(4) . . ?
C004 C005 C00C 118.4(3) 3_766 . ?
C008 C006 C007 121.0(3) . . ?
C006 C007 C009 118.6(3) . . ?
C006 C007 C00D 116.1(4) . . ?
C009 C007 C00D 125.3(4) . . ?
C006 C008 C00B 120.7(4) . . ?
C007 C009 C00A 120.5(4) . . ?
C00B C00A C009 119.7(3) . . ?
C008 C00B C00A 119.4(4) . . ?
C00D C00C C005 127.6(4) . . ?
C00C C00D C007 124.9(4) . . ?


_olex2_exptl_crystal_mounting_method 'mounted using grease'
_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 2.127
_oxdiff_exptl_absorpt_empirical_full_min 0.609
####################################################################### 
# 
# 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_730
_audit_block_doi                 10.5517/ccdc.csd.cc2m7hds
_database_code_depnum_ccdc_archive 'CCDC 2420275'
loop_
_audit_author_name
_audit_author_address
'Takumi Matsuo'
;Kochi University of Technology
Japan
;
_audit_update_record             
;
2025-01-29 deposited with the CCDC.	2025-04-14 downloaded from the CCDC.
;
_audit_creation_date             2024-07-08
_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         '2(C11 H7 O)'
_chemical_formula_sum            'C22 H14 O2'
_chemical_formula_weight         310.33
_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'
O O 0.0106 0.0060 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.7579(5)
_cell_length_b                   7.7062(6)
_cell_length_c                   17.0414(15)
_cell_angle_alpha                92.633(7)
_cell_angle_beta                 99.613(7)
_cell_angle_gamma                92.760(7)
_cell_volume                     743.55(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2815
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      29.6030
_cell_measurement_theta_min      2.4140
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.328
_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 colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             324
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.2575
0 1 0 0.2413
0 0 1 0.0075
0 0 -1 0.0245
-1 1 1 0.1996
1 -1 -1 0.2184
-1 -2 1 0.1922
1 2 -1 0.1903
2 1 -2 0.1772
-2 1 2 0.2012

_exptl_crystal_preparation       'mounted using grease'
_exptl_crystal_recrystallization_method sublimation
_exptl_crystal_size_max          0.433
_exptl_crystal_size_mid          0.383
_exptl_crystal_size_min          0.032
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
-0.0004 -0.9955 -0.0034 0.0279 -0.0480 0.0732
0.0004 0.9955 0.0034 -0.0279 0.0480 -0.0732
-0.0001 -0.0019 1.0054 0.0315 0.0283 0.0037
0.0001 0.0019 -1.0054 -0.0315 -0.0283 -0.0037
-1.0008 0.9949 1.0027 -0.0814 0.1288 0.0062
1.0008 -0.9949 -1.0027 0.0814 -0.1288 -0.0062
-1.0020 -1.9915 0.9926 0.0024 -0.0152 0.2259
1.0020 1.9915 -0.9926 -0.0024 0.0152 -0.2259
2.0028 0.9966 -1.9953 0.0789 -0.1136 -0.2321
-2.0021 0.9943 2.0020 -0.1348 0.2095 0.0857

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_av_unetI/netI     0.0520
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8786
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.361
_diffrn_reflns_theta_min         2.428
_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 0.997
_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    -40.00  59.00   0.50   68.93    --  -13.34  57.00   0.00  198
  2  ω     42.00  90.00   0.50   68.93    --   12.72 178.00   0.00   96
  3  ω    -69.00 -12.00   0.50   68.93    --  -13.34 124.00 -98.00  114
  4  ω    -79.00 -54.00   0.50   68.93    --  -13.34 147.00  66.00   50
  5  ω    -98.00 -41.00   0.50   68.93    --  -13.34 178.00   0.00  114
  6  ω    -68.00  17.00   0.50   68.93    --   12.72 -37.00-120.00  170
  7  ω     26.00  51.00   0.50   68.93    --   12.72-124.00-177.00   50
  8  ω    -53.00  31.00   0.50   68.93    --   12.72 -57.00-180.00  168
  9  ω     53.00  78.00   0.50   68.93    --   12.72-147.00  16.00   50
 10  ω     -7.00  32.00   0.50   68.93    --  -13.34 -99.00  30.00   78
;
_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      0.0846144000
_diffrn_orient_matrix_UB_12      -0.0281930000
_diffrn_orient_matrix_UB_13      0.0312974000
_diffrn_orient_matrix_UB_21      -0.0525533000
_diffrn_orient_matrix_UB_22      0.0481316000
_diffrn_orient_matrix_UB_23      0.0282026000
_diffrn_orient_matrix_UB_31      -0.0757571000
_diffrn_orient_matrix_UB_32      -0.0735222000
_diffrn_orient_matrix_UB_33      0.0035501000
_diffrn_oxdiff_digest_frames     
;
01ab19e0cc9082fc7c1a45ce05c6b132b5010882554
;
_diffrn_oxdiff_digest_hkl        
;
0159a20165f8ac806beb9e8d5b50f1c504b269
;
_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                2375
_reflns_number_total             3035
_reflns_odcompleteness_completeness 99.84
_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         0.416
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       0.005(2)
_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   1.115
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3035
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1320
_refine_ls_R_factor_gt           0.1143
_refine_ls_restrained_S_all      1.115
_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)+(0.0395P)²+5.1626P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2764
_refine_ls_wR_factor_ref         0.2837
_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:
 C008(H008), C009(H009), C00A(H00A), C00B(H00B), C00C(H00C), C00D(H00D),
 C00E(H00E), C00G(H00G), C00H(H00H), C00I(H00I), C00K(H00K), C00M(H00M),
 C00N(H00N), C00O(H00O)
;
_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
O001 O 0.8287(6) 0.2110(5) 0.6793(2) 0.0284(9) Uani 1 1 d . . . . .
O002 O 0.3393(7) 0.6096(5) 0.6969(3) 0.0396(10) Uani 1 1 d . . . . .
C003 C 1.0992(8) 0.2001(6) 0.7926(3) 0.0250(11) Uani 1 1 d . . . . .
C004 C 0.8761(9) 0.2539(6) 0.7590(3) 0.0253(11) Uani 1 1 d . . . . .
C005 C 0.6129(9) 0.7771(7) 0.7799(3) 0.0295(12) Uani 1 1 d . . . . .
C006 C 1.0243(9) 0.1264(6) 0.6617(3) 0.0273(12) Uani 1 1 d . . . . .
C007 C 1.0105(9) 0.0646(6) 0.5788(3) 0.0255(11) Uani 1 1 d . . . . .
C008 C 0.8134(9) 0.0906(7) 0.5207(3) 0.0282(12) Uani 1 1 d . . . . .
H008 H 0.685991 0.152001 0.534864 0.034 Uiso 1 1 calc R . . . .
C009 C 0.7301(9) 0.3384(7) 0.8039(3) 0.0289(12) Uani 1 1 d . . . . .
H009 H 0.580792 0.375021 0.779854 0.035 Uiso 1 1 calc R . . . .
C00A C 0.8043(9) 0.0280(6) 0.4437(3) 0.0276(11) Uani 1 1 d . . . . .
H00A H 0.670635 0.047403 0.404911 0.033 Uiso 1 1 calc R . . . .
C00B C 1.1868(9) 0.1186(6) 0.7268(3) 0.0276(11) Uani 1 1 d . . . . .
H00B H 1.334898 0.068012 0.729293 0.033 Uiso 1 1 calc R . . . .
C00C C 1.1763(9) 0.2313(7) 0.8738(3) 0.0308(12) Uani 1 1 d . . . . .
H00C H 1.326966 0.197236 0.897843 0.037 Uiso 1 1 calc R . . . .
C00D C 1.0309(9) 0.3130(7) 0.9196(3) 0.0295(12) Uani 1 1 d . . . . .
H00D H 1.081314 0.332553 0.975401 0.035 Uiso 1 1 calc R . . . .
C00E C 0.6835(9) 0.5372(7) 0.4597(4) 0.0331(13) Uani 1 1 d . . . . .
H00E H 0.811149 0.561406 0.432343 0.040 Uiso 1 1 calc R . . . .
C00F C 0.5118(10) 0.5690(7) 0.5783(3) 0.0289(12) Uani 1 1 d . . . . .
C00G C 0.8104(9) 0.3667(7) 0.8841(3) 0.0291(12) Uani 1 1 d . . . . .
H00G H 0.714553 0.423961 0.916329 0.035 Uiso 1 1 calc R . . . .
C00H C 0.6923(9) 0.6060(7) 0.5354(3) 0.0311(12) Uani 1 1 d . . . . .
H00H H 0.823769 0.680585 0.559245 0.037 Uiso 1 1 calc R . . . .
C00I C 0.2627(9) 0.6863(7) 0.8332(4) 0.0333(13) Uani 1 1 d . . . . .
H00I H 0.111931 0.626654 0.826755 0.040 Uiso 1 1 calc R . . . .
C00J C 0.3919(10) 0.6883(7) 0.7723(3) 0.0316(12) Uani 1 1 d . . . . .
C00K C 0.7096(9) 0.8673(7) 0.8508(4) 0.0336(13) Uani 1 1 d . . . . .
H00K H 0.859744 0.927848 0.856846 0.040 Uiso 1 1 calc R . . . .
C00L C 0.5276(11) 0.6442(8) 0.6583(4) 0.0397(15) Uani 1 1 d . . . . .
C00M C 0.6885(11) 0.7434(7) 0.7057(3) 0.0339(13) Uani 1 1 d . . . . .
H00M H 0.833750 0.786284 0.692442 0.041 Uiso 1 1 calc R . . . .
C00N C 0.5816(10) 0.8667(7) 0.9123(3) 0.0336(13) Uani 1 1 d . . . . .
H00N H 0.643365 0.929687 0.961180 0.040 Uiso 1 1 calc R . . . .
C00O C 0.3609(10) 0.7745(7) 0.9041(4) 0.0367(14) Uani 1 1 d . . . . .
H00O H 0.278692 0.773003 0.947984 0.044 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
O001 C004 1.362(6) . ?
O001 C006 1.396(6) . ?
O002 C00J 1.375(7) . ?
O002 C00L 1.381(7) . ?
C003 C004 1.406(7) . ?
C003 C00B 1.435(7) . ?
C003 C00C 1.386(8) . ?
C004 C009 1.391(7) . ?
C005 C00J 1.399(8) . ?
C005 C00K 1.383(8) . ?
C005 C00M 1.421(8) . ?
C006 C007 1.457(8) . ?
C006 C00B 1.333(8) . ?
C007 C008 1.405(7) . ?
C007 C00A 1.407(7) 2_756 ?
C008 C00A 1.368(8) . ?
C009 C00G 1.373(8) . ?
C00C C00D 1.389(8) . ?
C00D C00G 1.402(7) . ?
C00E C00F 1.405(8) 2_666 ?
C00E C00H 1.363(8) . ?
C00F C00H 1.392(8) . ?
C00F C00L 1.444(8) . ?
C00I C00J 1.375(8) . ?
C00I C00O 1.378(9) . ?
C00K C00N 1.380(8) . ?
C00L C00M 1.312(9) . ?
C00N C00O 1.408(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
C004 O001 C006 105.9(4) . . ?
C00J O002 C00L 108.0(5) . . ?
C004 C003 C00B 104.4(5) . . ?
C00C C003 C004 118.7(5) . . ?
C00C C003 C00B 136.9(5) . . ?
O001 C004 C003 110.7(4) . . ?
O001 C004 C009 126.7(5) . . ?
C009 C004 C003 122.7(5) . . ?
C00J C005 C00M 105.0(5) . . ?
C00K C005 C00J 120.0(5) . . ?
C00K C005 C00M 134.9(5) . . ?
O001 C006 C007 115.7(5) . . ?
C00B C006 O001 110.8(5) . . ?
C00B C006 C007 133.5(5) . . ?
C008 C007 C006 121.8(5) . . ?
C008 C007 C00A 118.6(5) . 2_756 ?
C00A C007 C006 119.6(5) 2_756 . ?
C00A C008 C007 120.3(5) . . ?
C00G C009 C004 117.3(5) . . ?
C008 C00A C007 121.1(5) . 2_756 ?
C006 C00B C003 108.1(5) . . ?
C003 C00C C00D 119.3(5) . . ?
C00C C00D C00G 120.6(5) . . ?
C00H C00E C00F 120.9(5) . 2_666 ?
C00E C00F C00L 122.5(5) 2_666 . ?
C00H C00F C00E 117.9(5) . 2_666 ?
C00H C00F C00L 119.5(5) . . ?
C009 C00G C00D 121.4(5) . . ?
C00E C00H C00F 121.1(5) . . ?
C00J C00I C00O 117.3(5) . . ?
O002 C00J C005 108.0(5) . . ?
C00I C00J O002 129.4(5) . . ?
C00I C00J C005 122.5(5) . . ?
C00N C00K C005 118.0(5) . . ?
O002 C00L C00F 117.2(6) . . ?
C00M C00L O002 109.1(5) . . ?
C00M C00L C00F 133.6(6) . . ?
C00L C00M C005 109.7(6) . . ?
C00K C00N C00O 121.2(5) . . ?
C00I C00O C00N 120.9(5) . . ?


_olex2_exptl_crystal_mounting_method loop
_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 1.595
_oxdiff_exptl_absorpt_empirical_full_min 0.726
####################################################################### 
# 
# 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_567
_audit_block_doi                 10.5517/ccdc.csd.cc2m7hbq
_database_code_depnum_ccdc_archive 'CCDC 2420273'
loop_
_audit_author_name
_audit_author_address
'Takumi Matsuo'
;Kochi University of Technology
Japan
;
_audit_update_record             
;
2025-01-29 deposited with the CCDC.	2025-04-14 downloaded from the CCDC.
;
_audit_creation_date             2024-03-04
_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         '2(C11 H5 F2 O)'
_chemical_formula_sum            'C22 H10 F4 O2'
_chemical_formula_weight         382.30
_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'
O O 0.0106 0.0060 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.0832(4)
_cell_length_b                   7.7303(4)
_cell_length_c                   17.5750(14)
_cell_angle_alpha                84.280(6)
_cell_angle_beta                 82.761(7)
_cell_angle_gamma                73.129(6)
_cell_volume                     782.85(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2819
_cell_measurement_temperature    103.15
_cell_measurement_theta_max      28.7080
_cell_measurement_theta_min      2.7460
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.638
_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    1.622
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             388
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.1378
0 -1 0 0.1201
1 0 0 0.1864
-1 0 0 0.2037
0 0 -1 0.0358
0 0 1 0.0113

_exptl_crystal_preparation       'mounted using grease'
_exptl_crystal_recrystallization_method sublimation
_exptl_crystal_size_max          0.494
_exptl_crystal_size_mid          0.258
_exptl_crystal_size_min          0.047
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 0.9997 -0.0000 -0.0783 -0.0111 0.0545
0.0003 -0.9997 0.0000 0.0783 0.0111 -0.0545
1.0004 0.0002 -0.0002 0.0926 0.0229 0.0769
-1.0004 -0.0002 0.0002 -0.0926 -0.0229 -0.0769
-0.0000 -0.0002 -0.9999 -0.0069 0.0401 0.0030
0.0000 0.0002 0.9999 0.0069 -0.0401 -0.0030

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_unetI/netI     0.0540
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_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       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9450
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         2.341
_diffrn_ambient_temperature      103.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -39.00  53.00   0.50   22.85    --  -13.34  57.00  60.00  184
  2  ω    -60.00 -34.00   0.50   22.85    --  -13.34 146.00 125.00   52
  3  ω    -71.00 -44.00   0.50   22.85    --  -13.34 125.00 -40.00   54
  4  ω     51.00  95.00   0.50   22.85    --   12.72 178.00-180.00   88
  5  ω    -61.00  20.00   0.50   22.85    --   12.72 -37.00 -60.00  162
  6  ω     21.00  57.00   0.50   22.85    --   12.72-125.00-119.00   72
  7  ω    -22.00  30.00   0.50   22.85    --  -13.34 -99.00-180.00  104
  8  ω    -62.00  40.00   0.50   22.85    --   12.72 -57.00-120.00  204
  9  ω     41.00  67.00   0.50   22.85    --   12.72-146.00  74.00   52
 10  ω    -71.00   4.00   0.50   22.85    --   12.72 -19.00 -30.00  150
;
_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      0.0925532000
_diffrn_orient_matrix_UB_12      -0.0783411000
_diffrn_orient_matrix_UB_13      0.0069018000
_diffrn_orient_matrix_UB_21      0.0228626000
_diffrn_orient_matrix_UB_22      -0.0110969000
_diffrn_orient_matrix_UB_23      -0.0400714000
_diffrn_orient_matrix_UB_31      0.0768981000
_diffrn_orient_matrix_UB_32      0.0545337000
_diffrn_orient_matrix_UB_33      -0.0030147000
_diffrn_oxdiff_digest_frames     
;
01c783ea436da66fba83b28b66a25c6c9101122fda5
;
_diffrn_oxdiff_digest_hkl        
;
010df45e84776dab0d074aa50fbbd089b98903
;
_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                2179
_reflns_number_total             3206
_reflns_odcompleteness_completeness 99.84
_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         0.260
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         3206
_refine_ls_number_restraints     26
_refine_ls_R_factor_all          0.0810
_refine_ls_R_factor_gt           0.0529
_refine_ls_restrained_S_all      1.054
_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)+(0.0892P)²+0.0808P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1397
_refine_ls_wR_factor_ref         0.1568
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 O006-C00K \\sim O0-C3
 with sigma of 0.02
 O006-C00O \\sim O0-C1
 with sigma of 0.02
 C007-C00I \\sim C0-C2
 with sigma of 0.02
 C007-C00O \\sim C0-C1
 with sigma of 0.02
 C00A-C00O \\sim C00A-C1
 with sigma of 0.02
 C00I-C00K \\sim C2-C3
 with sigma of 0.02
 C00I-C00P \\sim C2-C6
 with sigma of 0.02
 C00K-C00Q \\sim C3-C4
 with sigma of 0.02
 C00P-C00S \\sim C6-C00T
 with sigma of 0.02
 C00Q-C00R \\sim C4-C5
 with sigma of 0.02
 C00R-C00S \\sim C5-C00T
 with sigma of 0.02
 O006-C007 \\sim O0-C0
 with sigma of 0.04
 O006-C00A \\sim O0-C00A
 with sigma of 0.04
 O006-C00I \\sim O0-C2
 with sigma of 0.04
 O006-C00Q \\sim O0-C4
 with sigma of 0.04
 C007-C00A \\sim C0-C00A
 with sigma of 0.04
 C007-C00K \\sim C0-C3
 with sigma of 0.04
 C007-C00P \\sim C0-C6
 with sigma of 0.04
 C00I-C00O \\sim C2-C1
 with sigma of 0.04
 C00I-C00Q \\sim C2-C4
 with sigma of 0.04
 C00I-C00S \\sim C2-C00T
 with sigma of 0.04
 C00K-C00O \\sim C3-C1
 with sigma of 0.04
 C00K-C00P \\sim C3-C6
 with sigma of 0.04
 C00K-C00R \\sim C3-C5
 with sigma of 0.04
 C00P-C00R \\sim C6-C5
 with sigma of 0.04
 C00Q-C00S \\sim C4-C00T
 with sigma of 0.04
3. Others
 Sof(C1)=Sof(O0)=Sof(C0)=Sof(H0)=Sof(C2)=Sof(C3)=Sof(C4)=Sof(H4)=Sof(C5)=
 Sof(H5)=Sof(C00T)=Sof(H00T)=Sof(C6)=Sof(H6)=1-FVAR(1)
 Sof(O006)=Sof(C007)=Sof(H007)=Sof(C00I)=Sof(C00K)=Sof(C00O)=Sof(C00P)=
 Sof(H00P)=Sof(C00Q)=Sof(H00Q)=Sof(C00R)=Sof(H00R)=Sof(C00S)=Sof(H00S)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C007(H007), C00G(H00G), C00H(H00H), C00L(H00L), C00M(H00M), C00N(H00N),
 C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S), C0(H0), C4(H4), C5(H5),
 C00T(H00T), C6(H6)
;
_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 -0.3306(2) -0.13127(16) 0.95780(8) 0.0332(4) Uani 1 1 d . . . . .
F002 F -0.2659(2) 0.16188(17) 0.88631(8) 0.0354(4) Uani 1 1 d . . . . .
F003 F 0.2085(2) 0.70215(17) 0.60727(9) 0.0442(4) Uani 1 1 d . . . . .
F004 F 0.5471(3) 0.81429(17) 0.53971(9) 0.0443(4) Uani 1 1 d . . . . .
O005 O 0.2348(3) 0.39617(19) 0.93989(9) 0.0292(4) Uani 1 1 d . . . . .
O006 O 1.0323(9) 0.5400(7) 0.3788(4) 0.0274(14) Uani 0.562(10) 1 d D . P A 1
C007 C 0.9076(18) 0.8014(17) 0.4375(8) 0.033(2) Uani 0.562(10) 1 d D . P A 1
H007 H 0.817493 0.893056 0.469886 0.040 Uiso 0.562(10) 1 calc R . P A 1
C008 C -0.1642(4) -0.0707(3) 0.98115(13) 0.0275(5) Uani 1 1 d . . . . .
C009 C 0.0653(4) 0.3283(3) 0.91766(14) 0.0282(5) Uani 1 1 d . . . . .
C00A C 0.6894(4) 0.5639(3) 0.46180(13) 0.0273(5) Uani 1 1 d D . . . .
C00B C -0.1306(4) 0.0852(3) 0.94254(13) 0.0275(5) Uani 1 1 d . . . . .
C00C C 0.3485(4) 0.5976(3) 0.55417(14) 0.0298(5) Uani 1 1 d . . . . .
C00D C 0.0363(4) 0.1630(3) 0.95977(13) 0.0263(5) Uani 1 1 d . . . . .
C00E C 0.2292(4) 0.5507(3) 0.89319(13) 0.0277(5) Uani 1 1 d . . . . .
C00F C 0.5299(4) 0.6570(3) 0.51734(14) 0.0301(5) Uani 1 1 d . . . . .
C00G C 0.3707(4) 0.6608(3) 0.89486(14) 0.0309(5) Uani 1 1 d . . . . .
H00G H 0.485152 0.635571 0.929697 0.037 Uiso 1 1 calc R . . . .
C00H C -0.0424(4) 0.4352(3) 0.85987(14) 0.0328(5) Uani 1 1 d . . . . .
H00H H -0.162937 0.416585 0.835046 0.039 Uiso 1 1 calc R . . . .
C00I C 1.1111(19) 0.8085(15) 0.3889(8) 0.028(2) Uani 0.562(10) 1 d D . P A 1
C00J C 0.0597(4) 0.5815(3) 0.84323(14) 0.0316(5) Uani 1 1 d . . . . .
C00K C 1.1787(14) 0.6450(11) 0.3536(5) 0.0258(18) Uani 0.562(10) 1 d D . P A 1
C00L C 0.3358(4) 0.8102(3) 0.84275(14) 0.0340(6) Uani 1 1 d . . . . .
H00L H 0.430340 0.889370 0.841131 0.041 Uiso 1 1 calc R . . . .
C00M C 0.0255(4) 0.7349(3) 0.79181(15) 0.0400(6) Uani 1 1 d . . . . .
H00M H -0.090302 0.760929 0.757441 0.048 Uiso 1 1 calc R . . . .
C00N C 0.1649(4) 0.8475(3) 0.79239(15) 0.0380(6) Uani 1 1 d . . . . .
H00N H 0.144106 0.952323 0.757891 0.046 Uiso 1 1 calc R . . . .
C00O C 0.8650(9) 0.6464(8) 0.4301(4) 0.0253(15) Uani 0.562(10) 1 d D . P A 1
C00P C 1.2338(10) 0.9307(7) 0.3622(5) 0.0269(14) Uani 0.562(10) 1 d D . P A 1
H00P H 1.181426 1.050065 0.379187 0.032 Uiso 0.562(10) 1 calc R . P A 1
C00Q C 1.3753(9) 0.5894(9) 0.2989(3) 0.0296(14) Uani 0.562(10) 1 d D . P A 1
H00Q H 1.417973 0.474699 0.277525 0.035 Uiso 0.562(10) 1 calc R . P A 1
C00R C 1.4998(9) 0.7145(11) 0.2791(3) 0.0320(14) Uani 0.562(10) 1 d D . P A 1
H00R H 1.633669 0.685269 0.243334 0.038 Uiso 0.562(10) 1 calc R . P A 1
C00S C 1.4311(9) 0.8841(9) 0.3112(4) 0.0292(14) Uani 0.562(10) 1 d D . P A 1
H00S H 1.520684 0.966905 0.297745 0.035 Uiso 0.562(10) 1 calc R . P A 1
C1 C 0.8945(17) 0.6061(11) 0.4134(5) 0.022(2) Uiso 0.438(10) 1 d D . P A 2
O0 O 0.9208(19) 0.7750(13) 0.4287(6) 0.030(3) Uiso 0.438(10) 1 d D . P A 2
C0 C 1.055(3) 0.529(2) 0.3597(7) 0.031(3) Uiso 0.438(10) 1 d D . P A 2
H0 H 1.069357 0.415890 0.339614 0.037 Uiso 0.438(10) 1 calc R . P A 2
C2 C 1.205(2) 0.6408(16) 0.3365(6) 0.020(2) Uiso 0.438(10) 1 d D . P A 2
C3 C 1.109(3) 0.793(2) 0.3785(10) 0.024(4) Uiso 0.438(10) 1 d D . P A 2
C4 C 1.2125(18) 0.9351(13) 0.3865(5) 0.033(3) Uiso 0.438(10) 1 d D . P A 2
H4 H 1.155018 1.025227 0.422694 0.040 Uiso 0.438(10) 1 calc R . P A 2
C5 C 1.4033(17) 0.9231(12) 0.3356(5) 0.034(2) Uiso 0.438(10) 1 d D . P A 2
H5 H 1.477645 1.016252 0.333134 0.041 Uiso 0.438(10) 1 calc R . P A 2
C00T C 1.4976(16) 0.7806(12) 0.2861(5) 0.030(2) Uiso 0.438(10) 1 d D . P A 2
H00T H 1.630683 0.781530 0.251585 0.035 Uiso 0.438(10) 1 calc R . P A 2
C6 C 1.4005(16) 0.6418(12) 0.2871(5) 0.027(2) Uiso 0.438(10) 1 d D . P A 2
H6 H 1.467093 0.546106 0.253990 0.033 Uiso 0.438(10) 1 calc R . 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 C008 1.353(2) . ?
F002 C00B 1.345(3) . ?
F003 C00C 1.341(3) . ?
F004 C00F 1.350(2) . ?
O005 C009 1.396(2) . ?
O005 C00E 1.375(3) . ?
O006 C00K 1.377(9) . ?
O006 C00O 1.399(8) . ?
C007 C00I 1.425(14) . ?
C007 C00O 1.319(12) . ?
C008 C00B 1.379(3) . ?
C008 C00D 1.388(3) 2_557 ?
C009 C00D 1.456(3) . ?
C009 C00H 1.352(3) . ?
C00A C00C 1.394(3) 2_666 ?
C00A C00F 1.381(3) . ?
C00A C00O 1.426(5) . ?
C00A C1 1.517(9) . ?
C00B C00D 1.397(3) . ?
C00C C00F 1.379(3) . ?
C00E C00G 1.379(3) . ?
C00E C00J 1.391(3) . ?
C00G C00L 1.383(3) . ?
C00H C00J 1.431(3) . ?
C00I C00K 1.393(9) . ?
C00I C00P 1.379(11) . ?
C00J C00M 1.399(3) . ?
C00K C00Q 1.427(9) . ?
C00L C00N 1.398(3) . ?
C00M C00N 1.381(3) . ?
C00P C00S 1.384(8) . ?
C00Q C00R 1.386(8) . ?
C00R C00S 1.407(8) . ?
C1 O0 1.416(10) . ?
C1 C0 1.322(12) . ?
O0 C3 1.387(16) . ?
C0 C2 1.426(16) . ?
C2 C3 1.391(11) . ?
C2 C6 1.384(12) . ?
C3 C4 1.440(14) . ?
C4 C5 1.360(11) . ?
C5 C00T 1.413(9) . ?
C00T C6 1.365(9) . ?

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
C00E O005 C009 105.68(17) . . ?
C00K O006 C00O 104.1(5) . . ?
C00O C007 C00I 108.6(10) . . ?
F001 C008 C00B 116.0(2) . . ?
F001 C008 C00D 121.0(2) . 2_557 ?
C00B C008 C00D 123.0(2) . 2_557 ?
O005 C009 C00D 116.15(19) . . ?
C00H C009 O005 111.01(19) . . ?
C00H C009 C00D 132.8(2) . . ?
C00C C00A C00O 130.3(4) 2_666 . ?
C00C C00A C1 113.8(3) 2_666 . ?
C00F C00A C00C 113.9(2) . 2_666 ?
C00F C00A C00O 115.8(3) . . ?
C00F C00A C1 132.3(3) . . ?
F002 C00B C008 117.27(19) . . ?
F002 C00B C00D 120.2(2) . . ?
C008 C00B C00D 122.5(2) . . ?
F003 C00C C00A 120.7(2) . 2_666 ?
F003 C00C C00F 116.91(19) . . ?
C00F C00C C00A 122.4(2) . 2_666 ?
C008 C00D C009 124.9(2) 2_557 . ?
C008 C00D C00B 114.5(2) 2_557 . ?
C00B C00D C009 120.6(2) . . ?
O005 C00E C00G 125.4(2) . . ?
O005 C00E C00J 110.42(18) . . ?
C00G C00E C00J 124.2(2) . . ?
F004 C00F C00A 120.5(2) . . ?
F004 C00F C00C 115.7(2) . . ?
C00C C00F C00A 123.7(2) . . ?
C00E C00G C00L 116.0(2) . . ?
C009 C00H C00J 106.9(2) . . ?
C00K C00I C007 104.1(9) . . ?
C00P C00I C007 139.4(10) . . ?
C00P C00I C00K 115.9(10) . . ?
C00E C00J C00H 105.9(2) . . ?
C00E C00J C00M 118.8(2) . . ?
C00M C00J C00H 135.3(2) . . ?
O006 C00K C00I 111.5(8) . . ?
O006 C00K C00Q 123.3(7) . . ?
C00I C00K C00Q 125.2(9) . . ?
C00G C00L C00N 121.6(2) . . ?
C00N C00M C00J 118.1(2) . . ?
C00M C00N C00L 121.3(2) . . ?
O006 C00O C00A 113.5(5) . . ?
C007 C00O O006 111.6(6) . . ?
C007 C00O C00A 135.0(7) . . ?
C00I C00P C00S 121.7(7) . . ?
C00R C00Q C00K 115.2(5) . . ?
C00Q C00R C00S 121.1(5) . . ?
C00P C00S C00R 120.3(4) . . ?
O0 C1 C00A 112.1(7) . . ?
C0 C1 C00A 137.2(8) . . ?
C0 C1 O0 110.7(8) . . ?
C3 O0 C1 104.1(8) . . ?
C1 C0 C2 109.4(11) . . ?
C3 C2 C0 104.2(11) . . ?
C6 C2 C0 139.8(11) . . ?
C6 C2 C3 116.0(11) . . ?
O0 C3 C2 111.5(11) . . ?
O0 C3 C4 119.9(10) . . ?
C2 C3 C4 127.0(13) . . ?
C5 C4 C3 111.1(9) . . ?
C4 C5 C00T 124.0(9) . . ?
C6 C00T C5 121.1(9) . . ?
C00T C6 C2 119.8(8) . . ?


_olex2_exptl_crystal_mounting_method loop
_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 1.478
_oxdiff_exptl_absorpt_empirical_full_min 0.689
####################################################################### 
# 
# 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_219
_audit_block_doi                 10.5517/ccdc.csd.cc2m7h9p
_database_code_depnum_ccdc_archive 'CCDC 2420272'
loop_
_audit_author_name
_audit_author_address
'Takumi Matsuo'
;Kochi University of Technology
Japan
;
_audit_update_record             
;
2025-01-29 deposited with the CCDC.	2025-04-14 downloaded from the CCDC.
;
_audit_creation_date             2024-01-10
_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 H10 F4 O2'
_chemical_formula_sum            'C22 H10 F4 O2'
_chemical_formula_weight         382.30
_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'
O O 0.0106 0.0060 '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           9
_space_group_name_H-M_alt        'C 1 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'

_cell_length_a                   12.3696(4)
_cell_length_b                   18.8634(5)
_cell_length_c                   13.4159(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.178(3)
_cell_angle_gamma                90
_cell_volume                     3098.54(16)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5957
_cell_measurement_temperature    103.15
_cell_measurement_theta_max      29.9820
_cell_measurement_theta_min      2.1620
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.785
_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 colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.639
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1552
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 0 0.0561
1 0 0 0.0215
0 -1 0 0.0379
0 1 0 0.0329
0 0 1 0.1622
0 0 -1 0.1401

_exptl_crystal_preparation       'mounted using grease'
_exptl_crystal_recrystallization_method 'in solution'
_exptl_crystal_size_max          0.317
_exptl_crystal_size_mid          0.078
_exptl_crystal_size_min          0.071
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
-0.9997 0.0000 0.0003 -0.0137 0.0545 -0.0139
0.9997 -0.0000 -0.0003 0.0137 -0.0545 0.0139
-0.0002 -0.9996 0.0000 -0.0154 0.0048 0.0340
0.0002 0.9996 -0.0000 0.0154 -0.0048 -0.0340
0.0005 0.0003 0.9994 0.0484 0.0093 0.0206
-0.0005 -0.0003 -0.9994 -0.0484 -0.0093 -0.0206

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0170
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9408
_diffrn_reflns_point_group_measured_fraction_full 0.723
_diffrn_reflns_point_group_measured_fraction_max 0.711
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         1.983
_diffrn_ambient_temperature      103.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -9.00  93.00   0.50   62.63    --   12.72  33.00  61.00  204
  2  ω     66.00  92.00   0.50   62.63    --   12.72 178.00-180.00   52
  3  ω    -69.00  13.00   0.50   62.63    --   12.72 -33.00 -96.00  164
  4  ω    -22.00  32.00   0.50   62.63    --  -13.34 -99.00 150.00  108
;
_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      0.0136848000
_diffrn_orient_matrix_UB_12      0.0153638000
_diffrn_orient_matrix_UB_13      0.0483838000
_diffrn_orient_matrix_UB_21      -0.0545653000
_diffrn_orient_matrix_UB_22      -0.0047793000
_diffrn_orient_matrix_UB_23      0.0093423000
_diffrn_orient_matrix_UB_31      0.0138803000
_diffrn_orient_matrix_UB_32      -0.0339814000
_diffrn_orient_matrix_UB_33      0.0205833000
_diffrn_oxdiff_digest_frames     
;
01061f4d96375f11772af85853ba8e96ab005283b9a
;
_diffrn_oxdiff_digest_hkl        
;
017135cdfea2a1d954e44757e3d29ca9ee4323
;
_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         0.419
_reflns_Friedel_fraction_full    0.445
_reflns_Friedel_fraction_max     0.420
_reflns_number_gt                4034
_reflns_number_total             4496
_reflns_odcompleteness_completeness 99.97
_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         0.296
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details 
;
 Flack x determined using 1118 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     505
_refine_ls_number_reflns         4496
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0335
_refine_ls_restrained_S_all      1.085
_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)+(0.0662P)²+0.8513P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0997
_refine_ls_wR_factor_ref         0.1036
_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:
 C00E(H00E), C00H(H00H), C00J(H00J), C00S(H00S), C00W(H00W), C00X(H00X),
 C010(H010), C013(H013), C015(H015), C016(H016), C017(H017), C018(H018),
 C01A(H01A), C01B(H01B), C01E(H01E), C01F(H01F), C01G(H01G), C01H(H01H),
 C01J(H01J), C01K(H01K)
;
_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 0.18758(16) 0.48163(10) 0.66351(16) 0.0242(5) Uani 1 1 d . . . . .
F002 F 0.18364(16) 0.34352(10) 0.66389(16) 0.0261(5) Uani 1 1 d . . . . .
F003 F 0.43107(16) 0.18405(10) 0.40452(16) 0.0272(5) Uani 1 1 d . . . . .
F004 F 0.43885(15) 0.32053(10) 0.38614(17) 0.0273(5) Uani 1 1 d . . . . .
F005 F 0.55517(15) 0.47546(10) 0.59977(16) 0.0230(5) Uani 1 1 d . . . . .
F006 F 0.81706(15) 0.30532(10) 0.35974(16) 0.0260(5) Uani 1 1 d . . . . .
F007 F 0.54743(17) 0.33694(10) 0.59463(17) 0.0258(5) Uani 1 1 d . . . . .
F008 F 0.80816(15) 0.16871(10) 0.37856(17) 0.0264(5) Uani 1 1 d . . . . .
O009 O 0.5476(2) 0.43695(12) 0.38202(19) 0.0206(6) Uani 1 1 d . . . . .
O00A O 0.2837(2) 0.60145(12) 0.6282(2) 0.0277(6) Uani 1 1 d . . . . .
O00B O 0.69951(19) 0.05241(12) 0.38171(19) 0.0205(6) Uani 1 1 d . . . . .
O00C O 0.4492(2) 0.21793(12) 0.6653(2) 0.0301(6) Uani 1 1 d . . . . .
C00D C 0.3138(3) 0.67278(17) 0.6308(3) 0.0186(7) Uani 1 1 d . . . . .
C00E C 0.2782(3) 0.21458(15) 0.5891(3) 0.0190(7) Uani 1 1 d . . . . .
H00E H 0.209746 0.229147 0.558185 0.023 Uiso 1 1 calc R . . . .
C00F C 0.6191(3) 0.16853(18) 0.3931(3) 0.0199(8) Uani 1 1 d . . . . .
C00G C 0.4617(3) 0.44441(18) 0.6149(3) 0.0180(8) Uani 1 1 d . . . . .
C00H C 0.7183(3) 0.57883(17) 0.3194(3) 0.0216(8) Uani 1 1 d . . . . .
H00H H 0.786751 0.584013 0.299119 0.026 Uiso 1 1 calc R . . . .
C00I C 0.6105(3) 0.09188(16) 0.4018(3) 0.0184(7) Uani 1 1 d . . . . .
C00J C 0.5304(3) 0.04924(17) 0.4279(3) 0.0201(7) Uani 1 1 d . . . . .
H00J H 0.463427 0.063701 0.444761 0.024 Uiso 1 1 calc R . . . .
C00K C 0.4582(3) 0.37163(18) 0.6138(3) 0.0190(8) Uani 1 1 d . . . . .
C00L C 0.5284(3) 0.21234(18) 0.3948(3) 0.0206(8) Uani 1 1 d . . . . .
C00M C 0.7147(3) 0.20445(17) 0.3800(3) 0.0199(8) Uani 1 1 d . . . . .
C00N C 0.4207(3) 0.14685(17) 0.6528(3) 0.0201(8) Uani 1 1 d . . . . .
C00O C 0.3720(4) 0.48600(13) 0.6312(3) 0.0165(5) Uani 1 1 d . . . . .
C00P C 0.7190(3) 0.27692(18) 0.3698(3) 0.0204(8) Uani 1 1 d . . . . .
C00Q C 0.5688(3) -0.02214(17) 0.4242(3) 0.0192(8) Uani 1 1 d . . . . .
C00R C 0.6770(3) 0.51100(17) 0.3373(3) 0.0197(8) Uani 1 1 d . . . . .
C00S C 0.4816(3) 0.08791(18) 0.6798(3) 0.0253(8) Uani 1 1 d . . . . .
H00S H 0.553129 0.091331 0.712012 0.030 Uiso 1 1 calc R . . . .
C00T C 0.2791(3) 0.44799(17) 0.6464(3) 0.0166(7) Uani 1 1 d . . . . .
C00U C 0.5736(3) 0.50654(17) 0.3676(3) 0.0188(8) Uani 1 1 d . . . . .
C00V C 0.6723(3) -0.01681(18) 0.3951(3) 0.0199(8) Uani 1 1 d . . . . .
C00W C 0.4330(4) 0.02324(18) 0.6575(3) 0.0257(9) Uani 1 1 d . . . . .
H00W H 0.472187 -0.017915 0.675986 0.031 Uiso 1 1 calc R . . . .
C00X C 0.5510(3) 0.62996(18) 0.3629(3) 0.0229(8) Uani 1 1 d . . . . .
H00X H 0.510147 0.670380 0.371066 0.028 Uiso 1 1 calc R . . . .
C00Y C 0.6294(3) 0.32096(18) 0.3727(3) 0.0194(8) Uani 1 1 d . . . . .
C00Z C 0.3653(4) 0.33363(13) 0.6300(4) 0.0194(6) Uani 1 1 d . . . . .
C010 C 0.5082(3) 0.56398(18) 0.3807(3) 0.0211(8) Uani 1 1 d . . . . .
H010 H 0.439496 0.558797 0.400421 0.025 Uiso 1 1 calc R . . . .
C011 C 0.5328(3) 0.28504(18) 0.3849(3) 0.0206(8) Uani 1 1 d . . . . .
C012 C 0.2763(3) 0.37492(18) 0.6460(3) 0.0182(8) Uani 1 1 d . . . . .
C013 C 0.6548(3) 0.63724(17) 0.3327(3) 0.0243(8) Uani 1 1 d . . . . .
H013 H 0.681150 0.682305 0.321501 0.029 Uiso 1 1 calc R . . . .
C014 C 0.6374(3) 0.39741(17) 0.3619(3) 0.0195(7) Uani 1 1 d . . . . .
C015 C 0.7169(3) 0.43999(17) 0.3342(3) 0.0215(8) Uani 1 1 d . . . . .
H015 H 0.783693 0.425762 0.316783 0.026 Uiso 1 1 calc R . . . .
C016 C 0.4648(3) 0.60574(16) 0.6372(3) 0.0180(7) Uani 1 1 d . . . . .
H016 H 0.537173 0.591433 0.640694 0.022 Uiso 1 1 calc R . . . .
C017 C 0.2643(3) 0.07728(18) 0.5796(3) 0.0269(9) Uani 1 1 d . . . . .
H017 H 0.193357 0.073571 0.546056 0.032 Uiso 1 1 calc R . . . .
C018 C 0.5891(3) -0.14779(17) 0.4256(3) 0.0247(8) Uani 1 1 d . . . . .
H018 H 0.562147 -0.192857 0.435560 0.030 Uiso 1 1 calc R . . . .
C019 C 0.3773(4) 0.56315(14) 0.6319(4) 0.0232(6) Uani 1 1 d . . . . .
C01A C 0.2980(4) 0.79542(19) 0.6330(3) 0.0372(11) Uani 1 1 d . . . . .
H01A H 0.255515 0.836155 0.632365 0.045 Uiso 1 1 calc R . . . .
C01B C 0.6931(3) -0.14100(19) 0.3960(3) 0.0240(8) Uani 1 1 d . . . . .
H01B H 0.733461 -0.181539 0.387300 0.029 Uiso 1 1 calc R . . . .
C01C C 0.3577(4) 0.25625(15) 0.6260(3) 0.0278(9) Uani 1 1 d . . . . .
C01D C 0.3131(3) 0.14317(17) 0.6040(3) 0.0224(8) Uani 1 1 d . . . . .
C01E C 0.2478(3) 0.73083(19) 0.6290(3) 0.0309(9) Uani 1 1 d . . . . .
H01E H 0.172395 0.726613 0.625168 0.037 Uiso 1 1 calc R . . . .
C01F C 0.5258(3) -0.08935(17) 0.4402(3) 0.0252(8) Uani 1 1 d . . . . .
H01F H 0.457121 -0.094404 0.459850 0.030 Uiso 1 1 calc R . . . .
C01G C 0.7365(3) -0.07504(18) 0.3797(3) 0.0219(8) Uani 1 1 d . . . . .
H01G H 0.805022 -0.070050 0.359541 0.026 Uiso 1 1 calc R . . . .
C01H C 0.3271(4) 0.01787(18) 0.6081(3) 0.0306(9) Uani 1 1 d . . . . .
H01H H 0.297284 -0.026855 0.593626 0.037 Uiso 1 1 calc R . . . .
C01I C 0.4268(3) 0.67600(18) 0.6364(3) 0.0213(8) Uani 1 1 d . . . . .
C01J C 0.4771(3) 0.7432(2) 0.6400(3) 0.0349(10) Uani 1 1 d . . . . .
H01J H 0.552445 0.747798 0.643582 0.042 Uiso 1 1 calc R . . . .
C01K C 0.4101(4) 0.8022(2) 0.6379(3) 0.0408(12) Uani 1 1 d . . . . .
H01K H 0.441021 0.847248 0.639921 0.049 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 C00T 1.346(4) . ?
F002 C012 1.342(4) . ?
F003 C00L 1.340(4) . ?
F004 C011 1.344(4) . ?
F005 C00G 1.337(4) . ?
F006 C00P 1.351(4) . ?
F007 C00K 1.339(4) . ?
F008 C00M 1.341(4) . ?
O009 C00U 1.372(4) . ?
O009 C014 1.396(4) . ?
O00A C00D 1.395(4) . ?
O00A C019 1.359(5) . ?
O00B C00I 1.387(4) . ?
O00B C00V 1.366(4) . ?
O00C C00N 1.391(4) . ?
O00C C01C 1.383(5) . ?
C00D C01E 1.364(5) . ?
C00D C01I 1.390(4) . ?
C00E C01C 1.301(6) . ?
C00E C01D 1.420(4) . ?
C00F C00I 1.456(4) . ?
C00F C00L 1.396(5) . ?
C00F C00M 1.396(5) . ?
C00G C00K 1.374(5) . ?
C00G C00O 1.402(5) . ?
C00H C00R 1.411(5) . ?
C00H C013 1.380(5) . ?
C00I C00J 1.360(5) . ?
C00J C00Q 1.431(5) . ?
C00K C00Z 1.397(5) . ?
C00L C011 1.380(5) . ?
C00M C00P 1.376(5) . ?
C00N C00S 1.363(5) . ?
C00N C01D 1.398(4) . ?
C00O C00T 1.394(5) . ?
C00O C019 1.457(3) . ?
C00P C00Y 1.390(5) . ?
C00Q C00V 1.394(5) . ?
C00Q C01F 1.403(5) . ?
C00R C00U 1.397(5) . ?
C00R C015 1.430(5) . ?
C00S C00W 1.374(5) . ?
C00T C012 1.379(5) . ?
C00U C010 1.379(5) . ?
C00V C01G 1.388(5) . ?
C00W C01H 1.385(5) . ?
C00X C010 1.387(5) . ?
C00X C013 1.407(5) . ?
C00Y C011 1.403(5) . ?
C00Y C014 1.454(5) . ?
C00Z C012 1.390(5) . ?
C00Z C01C 1.463(4) . ?
C014 C015 1.362(5) . ?
C016 C019 1.342(5) . ?
C016 C01I 1.406(5) . ?
C017 C01D 1.400(5) . ?
C017 C01H 1.386(5) . ?
C018 C01B 1.404(5) . ?
C018 C01F 1.382(5) . ?
C01A C01E 1.365(6) . ?
C01A C01K 1.386(6) . ?
C01B C01G 1.385(5) . ?
C01I C01J 1.411(5) . ?
C01J C01K 1.385(6) . ?

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
C00U O009 C014 105.9(3) . . ?
C019 O00A C00D 106.8(3) . . ?
C00V O00B C00I 105.7(3) . . ?
C01C O00C C00N 106.1(3) . . ?
C01E C00D O00A 128.1(3) . . ?
C01E C00D C01I 124.1(4) . . ?
C01I C00D O00A 107.8(3) . . ?
C01C C00E C01D 108.7(3) . . ?
C00L C00F C00I 121.2(3) . . ?
C00M C00F C00I 124.4(3) . . ?
C00M C00F C00L 114.3(3) . . ?
F005 C00G C00K 117.6(3) . . ?
F005 C00G C00O 120.0(3) . . ?
C00K C00G C00O 122.5(3) . . ?
C013 C00H C00R 118.4(3) . . ?
O00B C00I C00F 116.7(3) . . ?
C00J C00I O00B 111.1(3) . . ?
C00J C00I C00F 132.2(4) . . ?
C00I C00J C00Q 106.8(3) . . ?
F007 C00K C00G 117.7(3) . . ?
F007 C00K C00Z 119.8(3) . . ?
C00G C00K C00Z 122.5(3) . . ?
F003 C00L C00F 120.1(3) . . ?
F003 C00L C011 117.0(3) . . ?
C011 C00L C00F 122.9(3) . . ?
F008 C00M C00F 120.4(3) . . ?
F008 C00M C00P 116.9(3) . . ?
C00P C00M C00F 122.7(3) . . ?
O00C C00N C01D 108.2(3) . . ?
C00S C00N O00C 129.3(4) . . ?
C00S C00N C01D 122.5(3) . . ?
C00G C00O C019 121.6(4) . . ?
C00T C00O C00G 115.0(2) . . ?
C00T C00O C019 123.4(4) . . ?
F006 C00P C00M 116.9(3) . . ?
F006 C00P C00Y 119.8(3) . . ?
C00M C00P C00Y 123.3(3) . . ?
C00V C00Q C00J 105.3(3) . . ?
C00V C00Q C01F 119.4(3) . . ?
C01F C00Q C00J 135.2(4) . . ?
C00H C00R C015 135.2(3) . . ?
C00U C00R C00H 118.2(3) . . ?
C00U C00R C015 106.6(3) . . ?
C00N C00S C00W 117.3(4) . . ?
F001 C00T C00O 120.9(3) . . ?
F001 C00T C012 116.8(3) . . ?
C012 C00T C00O 122.3(3) . . ?
O009 C00U C00R 110.0(3) . . ?
O009 C00U C010 125.4(3) . . ?
C010 C00U C00R 124.6(3) . . ?
O00B C00V C00Q 111.0(3) . . ?
O00B C00V C01G 125.4(3) . . ?
C01G C00V C00Q 123.5(3) . . ?
C00S C00W C01H 121.6(4) . . ?
C010 C00X C013 121.6(3) . . ?
C00P C00Y C011 114.2(3) . . ?
C00P C00Y C014 121.6(3) . . ?
C011 C00Y C014 124.2(3) . . ?
C00K C00Z C01C 123.8(4) . . ?
C012 C00Z C00K 115.1(2) . . ?
C012 C00Z C01C 121.1(4) . . ?
C00U C010 C00X 115.9(3) . . ?
F004 C011 C00L 116.6(3) . . ?
F004 C011 C00Y 120.9(3) . . ?
C00L C011 C00Y 122.5(3) . . ?
F002 C012 C00T 117.5(3) . . ?
F002 C012 C00Z 119.7(3) . . ?
C00T C012 C00Z 122.7(3) . . ?
C00H C013 C00X 121.3(3) . . ?
O009 C014 C00Y 116.3(3) . . ?
C015 C014 O009 111.3(3) . . ?
C015 C014 C00Y 132.4(3) . . ?
C014 C015 C00R 106.2(3) . . ?
C019 C016 C01I 107.3(3) . . ?
C01H C017 C01D 116.6(4) . . ?
C01F C018 C01B 121.8(3) . . ?
O00A C019 C00O 119.6(4) . . ?
C016 C019 O00A 111.1(2) . . ?
C016 C019 C00O 129.3(4) . . ?
C01E C01A C01K 122.1(4) . . ?
C01G C01B C018 121.2(3) . . ?
O00C C01C C00Z 117.5(4) . . ?
C00E C01C O00C 111.3(2) . . ?
C00E C01C C00Z 131.2(4) . . ?
C00N C01D C00E 105.6(3) . . ?
C00N C01D C017 120.2(3) . . ?
C017 C01D C00E 134.2(4) . . ?
C00D C01E C01A 116.6(4) . . ?
C018 C01F C00Q 117.7(3) . . ?
C01B C01G C00V 116.4(4) . . ?
C00W C01H C017 121.8(4) . . ?
C00D C01I C016 107.0(3) . . ?
C00D C01I C01J 118.5(4) . . ?
C016 C01I C01J 134.6(4) . . ?
C01K C01J C01I 117.5(4) . . ?
C01J C01K C01A 121.2(4) . . ?


_olex2_exptl_crystal_mounting_method loop
_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 1.099
_oxdiff_exptl_absorpt_empirical_full_min 0.849
####################################################################### 
# 
# 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_938
_audit_block_doi                 10.5517/ccdc.csd.cc2m7hft
_database_code_depnum_ccdc_archive 'CCDC 2420276'
loop_
_audit_author_name
_audit_author_address
'Takumi Matsuo'
;Kochi University of Technology
Japan
;
_audit_update_record             
;
2025-01-29 deposited with the CCDC.	2025-04-14 downloaded from the CCDC.
;
_audit_creation_date             2025-01-14
_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         '1(C22 H14 O2)'
_chemical_formula_sum            'C22 H14 O2'
_chemical_formula_weight         310.33
_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'
O O 0.0106 0.0060 '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                   5.7690(2)
_cell_length_b                   33.1202(12)
_cell_length_c                   7.7842(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.360(3)
_cell_angle_gamma                90
_cell_volume                     1484.77(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7277
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      30.0210
_cell_measurement_theta_min      2.8880
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.941
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.796
_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 colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             648
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0959
0 0 1 0.3580
1 0 1 0.0475
-1 0 -1 0.0720
0 1 0 0.0923
0 -1 0 0.0113

_exptl_crystal_preparation       'in soln'
_exptl_crystal_recrystallization_method 'in soln'
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
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
0.4992 0.0027 -0.5006 -0.0002 -0.0195 0.0718
-0.4992 -0.0027 0.5006 0.0002 0.0195 -0.0718
0.5001 0.0010 0.5001 0.0083 0.0663 0.0417
-0.5001 -0.0010 -0.5001 -0.0083 -0.0663 -0.0417
-0.0003 1.0003 -0.0002 0.0213 -0.0023 -0.0005
0.0003 -1.0003 0.0002 -0.0213 0.0023 0.0005

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_Laue_measured_fraction_full 1.000
_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       32
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            13911
_diffrn_reflns_point_group_measured_fraction_full 0.845
_diffrn_reflns_point_group_measured_fraction_max 0.830
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.460
_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 1.000
_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    -66.00   4.00   0.50   29.88    --   12.72 -19.00 120.00  140
  2  ω     37.00  75.00   0.50   29.88    --   12.72-130.00 -42.00   76
  3  ω     43.00  74.00   0.50   29.88    --   12.72-178.00 -30.00   62
  4  ω     36.00  61.00   0.50   29.88    --   12.72-139.00 143.00   50
  5  ω    -17.00  32.00   0.50   29.88    --  -13.34 -99.00 -30.00   98
  6  ω    -58.00  21.00   0.50   29.88    --   12.72 -37.00-150.00  158
  7  ω    -70.00 -45.00   0.50   29.88    --  -13.34 130.00  29.00   50
  8  ω    -75.00 -50.00   0.50   29.88    --  -13.34 139.00-156.00   50
  9  ω     44.00  71.00   0.50   29.88    --   12.72 178.00-150.00   54
 10  ω    -97.00 -45.00   0.50   29.88    --  -13.34-178.00  30.00  104
;
_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      0.0080818000
_diffrn_orient_matrix_UB_12      0.0212931000
_diffrn_orient_matrix_UB_13      0.0084770000
_diffrn_orient_matrix_UB_21      0.0469604000
_diffrn_orient_matrix_UB_22      -0.0022810000
_diffrn_orient_matrix_UB_23      0.0856992000
_diffrn_orient_matrix_UB_31      0.1135381000
_diffrn_orient_matrix_UB_32      -0.0005202000
_diffrn_orient_matrix_UB_33      -0.0302503000
_diffrn_oxdiff_digest_frames     
;
01759718bb52ec6c367eab39fc607fe50700842c1f1
;
_diffrn_oxdiff_digest_hkl        
;
01092e80fba3a3d07c23c7d7ea3eacae534dad
;
_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         0.632
_reflns_Friedel_fraction_full    0.684
_reflns_Friedel_fraction_max     0.655
_reflns_number_gt                4601
_reflns_number_total             5043
_reflns_odcompleteness_completeness 99.90
_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         0.245
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 
;
 Flack x determined using 1575 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     470
_refine_ls_number_reflns         5043
_refine_ls_number_restraints     27
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0596
_refine_ls_restrained_S_all      1.074
_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)+(0.0510P)²+1.4154P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1416
_refine_ls_wR_factor_ref         0.1445
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 O004-C00Q \\sim O0-C2
 with sigma of 0.02
 O004-C01C \\sim O0-C01D
 with sigma of 0.02
 C00Q-C00R \\sim C2-C3
 with sigma of 0.02
 C00Q-C01A \\sim C2-C4
 with sigma of 0.02
 C00R-C00V \\sim C3-C1
 with sigma of 0.02
 C00R-C019 \\sim C3-C0
 with sigma of 0.02
 C00V-C01C \\sim C1-C01D
 with sigma of 0.02
 C014-C01C \\sim C014-C01D
 with sigma of 0.02
 C017-C019 \\sim C6-C0
 with sigma of 0.02
 C017-C01B \\sim C6-C5
 with sigma of 0.02
 C01A-C01B \\sim C4-C5
 with sigma of 0.02
 O004-C00R \\sim O0-C3
 with sigma of 0.04
 O004-C00V \\sim O0-C1
 with sigma of 0.04
 O004-C014 \\sim O0-C014
 with sigma of 0.04
 O004-C01A \\sim O0-C4
 with sigma of 0.04
 C00Q-C00V \\sim C2-C1
 with sigma of 0.04
 C00Q-C019 \\sim C2-C0
 with sigma of 0.04
 C00Q-C01B \\sim C2-C5
 with sigma of 0.04
 C00Q-C01C \\sim C2-C01D
 with sigma of 0.04
 C00R-C017 \\sim C3-C6
 with sigma of 0.04
 C00R-C01A \\sim C3-C4
 with sigma of 0.04
 C00R-C01C \\sim C3-C01D
 with sigma of 0.04
 C00V-C014 \\sim C1-C014
 with sigma of 0.04
 C00V-C019 \\sim C1-C0
 with sigma of 0.04
 C017-C01A \\sim C6-C4
 with sigma of 0.04
 C019-C01B \\sim C0-C5
 with sigma of 0.04
3. Others
 Sof(C01D)=Sof(O0)=Sof(C1)=Sof(H1)=Sof(C2)=Sof(C3)=Sof(C4)=Sof(H4)=Sof(C0)=
 Sof(H0)=Sof(C5)=Sof(H5)=Sof(C6)=Sof(H6)=1-FVAR(1)
 Sof(O004)=Sof(C00Q)=Sof(C00R)=Sof(C00V)=Sof(H00V)=Sof(C017)=Sof(H017)=
 Sof(C019)=Sof(H019)=Sof(C01A)=Sof(H01A)=Sof(C01B)=Sof(H01B)=Sof(C01C)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C008(H008), C009(H009), C00B(H00B), C00D(H00D), C00G(H00G), C00H(H00H),
 C00J(H00J), C00L(H00L), C00M(H00M), C00O(H00O), C00P(H00P), C00S(H00S),
 C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X), C00Y(H00Y), C00Z(H00Z),
 C010(H010), C012(H012), C013(H013), C015(H015), C016(H016), C017(H017),
 C018(H018), C019(H019), C01A(H01A), C01B(H01B), C1(H1), C4(H4), C0(H0), C5(H5),
  C6(H6)
;
_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
O001 O -1.2209(5) -0.41165(10) 0.0423(4) 0.0304(8) Uani 1 1 d . . . . .
O002 O -0.6781(5) -0.58852(11) -0.3506(4) 0.0314(8) Uani 1 1 d . . . . .
O003 O -0.1799(6) -0.59540(11) -0.7417(5) 0.0387(9) Uani 1 1 d . . . . .
O004 O -0.7078(16) -0.3998(2) -0.5542(8) 0.0237(19) Uani 0.594(18) 1 d D . P A
1
C005 C -1.0145(7) -0.35374(15) 0.0227(6) 0.0265(10) Uani 1 1 d . . . . .
C006 C -0.9141(8) -0.54029(15) -0.2114(6) 0.0263(10) Uani 1 1 d . . . . .
C007 C -0.6768(8) -0.62916(15) -0.3893(6) 0.0255(10) Uani 1 1 d . . . . .
C008 C -1.1478(7) -0.49111(15) -0.0698(6) 0.0280(11) Uani 1 1 d . . . . .
H008 H -1.283500 -0.484952 -0.011510 0.034 Uiso 1 1 calc R . . . .
C009 C -0.7888(7) -0.47119(16) -0.1848(6) 0.0274(11) Uani 1 1 d . . . . .
H009 H -0.676964 -0.451026 -0.206171 0.033 Uiso 1 1 calc R . . . .
C00A C -1.2163(8) -0.37123(15) 0.0796(6) 0.0278(11) Uani 1 1 d . . . . .
C00B C -1.0047(8) -0.61516(15) -0.2553(6) 0.0285(11) Uani 1 1 d . . . . .
H00B H -1.150186 -0.617558 -0.205056 0.034 Uiso 1 1 calc R . . . .
C00C C -1.0171(8) -0.41967(17) -0.0404(6) 0.0308(11) Uani 1 1 d . . . . .
C00D C -0.5067(8) -0.64954(16) -0.4683(6) 0.0298(11) Uani 1 1 d . . . . .
H00D H -0.373332 -0.636077 -0.505852 0.036 Uiso 1 1 calc R . . . .
C00E C -0.9888(8) -0.46087(15) -0.0963(6) 0.0260(10) Uani 1 1 d . . . . .
C00F C -0.1877(8) -0.63328(15) -0.8169(6) 0.0283(11) Uani 1 1 d . . . . .
C00G C -0.7557(8) -0.50989(16) -0.2396(6) 0.0293(11) Uani 1 1 d . . . . .
H00G H -0.620492 -0.516088 -0.298444 0.035 Uiso 1 1 calc R . . . .
C00H C -1.3847(8) -0.34952(16) 0.1601(6) 0.0304(11) Uani 1 1 d . . . . .
H00H H -1.521153 -0.361985 0.197616 0.036 Uiso 1 1 calc R . . . .
C00I C -0.4036(8) -0.63792(16) -0.9080(6) 0.0309(11) Uani 1 1 d . . . . .
C00J C -0.0201(8) -0.66296(17) -0.8073(6) 0.0334(11) Uani 1 1 d . . . . .
H00J H 0.125560 -0.659072 -0.746088 0.040 Uiso 1 1 calc R . . . .
C00K C -0.4229(9) -0.53687(15) -0.7143(6) 0.0322(11) Uani 1 1 d . . . . .
C00L C -0.8933(8) -0.38584(16) -0.0540(6) 0.0285(11) Uani 1 1 d . . . . .
H00L H -0.748907 -0.383601 -0.105928 0.034 Uiso 1 1 calc R . . . .
C00M C -1.1140(8) -0.52995(16) -0.1259(6) 0.0304(11) Uani 1 1 d . . . . .
H00M H -1.227107 -0.550039 -0.106755 0.036 Uiso 1 1 calc R . . . .
C00N C -0.8770(8) -0.64749(15) -0.3329(6) 0.0272(11) Uani 1 1 d . . . . .
C00O C -0.9088(8) -0.68850(16) -0.3595(7) 0.0334(12) Uani 1 1 d . . . . .
H00O H -1.044717 -0.701670 -0.324807 0.040 Uiso 1 1 calc R . . . .
C00P C -1.3428(8) -0.30885(16) 0.1825(6) 0.0327(12) Uani 1 1 d . . . . .
H00P H -1.452693 -0.292742 0.237612 0.039 Uiso 1 1 calc R . . . .
C00Q C -0.693(2) -0.3610(3) -0.4801(13) 0.023(3) Uani 0.594(18) 1 d D . P A 1
C00R C -0.474(2) -0.3579(4) -0.3901(14) 0.024(3) Uani 0.594(18) 1 d D . P A 1
C00S C -0.2533(8) -0.51795(17) -0.6096(6) 0.0349(12) Uani 1 1 d . . . . .
H00S H -0.112027 -0.531666 -0.579806 0.042 Uiso 1 1 calc R . . . .
C00T C -0.8816(8) -0.58184(16) -0.2675(6) 0.0318(12) Uani 1 1 d . . . . .
C00U C -0.5266(9) -0.60122(15) -0.8828(7) 0.0335(12) Uani 1 1 d . . . . .
H00U H -0.678641 -0.595064 -0.928867 0.040 Uiso 1 1 calc R . . . .
C00V C -0.360(2) -0.3939(3) -0.4136(13) 0.026(2) Uani 0.594(18) 1 d D . P A 1
H00V H -0.208881 -0.400303 -0.367093 0.031 Uiso 0.594(18) 1 calc R . P A 1
C00W C -0.5370(9) -0.69013(17) -0.4908(7) 0.0350(12) Uani 1 1 d . . . . .
H00W H -0.420438 -0.705299 -0.543190 0.042 Uiso 1 1 calc R . . . .
C00X C -0.6294(8) -0.51650(16) -0.7534(7) 0.0335(11) Uani 1 1 d . . . . .
H00X H -0.747971 -0.529160 -0.824116 0.040 Uiso 1 1 calc R . . . .
C00Y C -0.4522(9) -0.67400(17) -0.9924(7) 0.0388(13) Uani 1 1 d . . . . .
H00Y H -0.596708 -0.678144 -1.054756 0.047 Uiso 1 1 calc R . . . .
C00Z C -0.0753(10) -0.69855(17) -0.8912(7) 0.0385(13) Uani 1 1 d . . . . .
H00Z H 0.033264 -0.720152 -0.885879 0.046 Uiso 1 1 calc R . . . .
C010 C -0.9786(8) -0.31267(16) 0.0462(6) 0.0340(12) Uani 1 1 d . . . . .
H010 H -0.843375 -0.299924 0.007978 0.041 Uiso 1 1 calc R . . . .
C011 C -0.3938(9) -0.57755(16) -0.7855(7) 0.0383(13) Uani 1 1 d . . . . .
C012 C -0.6651(9) -0.47813(16) -0.6912(6) 0.0345(12) Uani 1 1 d . . . . .
H012 H -0.808026 -0.464757 -0.719249 0.041 Uiso 1 1 calc R . . . .
C013 C -0.2870(9) -0.47959(18) -0.5482(7) 0.0385(13) Uani 1 1 d . . . . .
H013 H -0.167890 -0.467003 -0.477723 0.046 Uiso 1 1 calc R . . . .
C014 C -0.4945(10) -0.45886(16) -0.5881(7) 0.0353(12) Uani 1 1 d D . . . .
C015 C -0.7360(9) -0.71003(16) -0.4385(7) 0.0354(12) Uani 1 1 d . . . . .
H015 H -0.753250 -0.738254 -0.457018 0.042 Uiso 1 1 calc R . . . .
C016 C -1.1435(9) -0.29095(17) 0.1263(6) 0.0336(11) Uani 1 1 d . . . . .
H016 H -1.120611 -0.262807 0.143780 0.040 Uiso 1 1 calc R . . . .
C017 C -0.6004(19) -0.2897(4) -0.3153(13) 0.025(3) Uani 0.594(18) 1 d D . P A 1
H017 H -0.572832 -0.264281 -0.261004 0.030 Uiso 0.594(18) 1 calc R . P A 1
C018 C -0.2862(10) -0.70348(17) -0.9834(7) 0.0405(13) Uani 1 1 d . . . . .
H018 H -0.316551 -0.728206 -1.042349 0.049 Uiso 1 1 calc R . . . .
C019 C -0.4326(18) -0.3195(4) -0.3056(13) 0.020(2) Uani 0.594(18) 1 d D . P A 1
H019 H -0.288967 -0.314639 -0.242920 0.024 Uiso 0.594(18) 1 calc R . P A 1
C01A C -0.8638(19) -0.3339(4) -0.4922(16) 0.027(3) Uani 0.594(18) 1 d D . P A 1
H01A H -1.008303 -0.338801 -0.553484 0.032 Uiso 0.594(18) 1 calc R . P A 1
C01B C -0.811(2) -0.2975(5) -0.4064(16) 0.028(3) Uani 0.594(18) 1 d D . P A 1
H01B H -0.926079 -0.276895 -0.410594 0.033 Uiso 0.594(18) 1 calc R . P A 1
C01C C -0.4975(18) -0.4188(2) -0.5130(11) 0.022(2) Uani 0.594(18) 1 d D . P A 1
C01D C -0.595(3) -0.4198(4) -0.543(2) 0.030(4) Uiso 0.406(18) 1 d D . P A 2
O0 O -0.428(2) -0.3979(4) -0.4469(19) 0.033(4) Uiso 0.406(18) 1 d D . P A 2
C1 C -0.788(3) -0.3970(5) -0.567(2) 0.028(5) Uiso 0.406(18) 1 d D . P A 2
H1 H -0.926377 -0.405349 -0.629655 0.034 Uiso 0.406(18) 1 calc R . P A 2
C2 C -0.531(3) -0.3594(5) -0.415(3) 0.026(5) Uiso 0.406(18) 1 d D . P A 2
C3 C -0.759(3) -0.3597(6) -0.487(3) 0.029(6) Uiso 0.406(18) 1 d D . P A 2
C4 C -0.414(3) -0.3310(6) -0.320(3) 0.024(5) Uiso 0.406(18) 1 d D . P A 2
H4 H -0.263681 -0.335265 -0.266500 0.029 Uiso 0.406(18) 1 calc R . P A 2
C0 C -0.868(4) -0.3216(6) -0.475(3) 0.028(5) Uiso 0.406(18) 1 d D . P A 2
H0 H -1.018225 -0.317877 -0.529059 0.033 Uiso 0.406(18) 1 calc R . P A 2
C5 C -0.537(3) -0.2948(6) -0.307(2) 0.022(4) Uiso 0.406(18) 1 d D . P A 2
H5 H -0.467516 -0.273085 -0.243223 0.027 Uiso 0.406(18) 1 calc R . P A 2
C6 C -0.763(4) -0.2896(7) -0.386(3) 0.037(6) Uiso 0.406(18) 1 d D . P A 2
H6 H -0.841106 -0.264471 -0.378529 0.045 Uiso 0.406(18) 1 calc R . 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
O001 C00A 1.370(6) . ?
O001 C00C 1.399(5) . ?
O002 C007 1.379(6) . ?
O002 C00T 1.391(5) . ?
O003 C00F 1.384(6) . ?
O003 C011 1.393(6) . ?
O004 C00Q 1.410(12) . ?
O004 C01C 1.387(10) . ?
C005 C00A 1.396(7) . ?
C005 C00L 1.422(7) . ?
C005 C010 1.387(7) . ?
C006 C00G 1.386(7) . ?
C006 C00M 1.407(6) . ?
C006 C00T 1.459(7) . ?
C007 C00D 1.366(7) . ?
C007 C00N 1.398(6) . ?
C008 C00E 1.382(7) . ?
C008 C00M 1.376(7) . ?
C009 C00E 1.420(6) . ?
C009 C00G 1.368(7) . ?
C00A C00H 1.387(7) . ?
C00B C00N 1.451(7) . ?
C00B C00T 1.319(7) . ?
C00C C00E 1.445(7) . ?
C00C C00L 1.336(7) . ?
C00D C00W 1.366(8) . ?
C00F C00I 1.405(7) . ?
C00F C00J 1.378(7) . ?
C00H C00P 1.378(7) . ?
C00I C00U 1.427(7) . ?
C00I C00Y 1.385(8) . ?
C00J C00Z 1.376(8) . ?
C00K C00S 1.386(7) . ?
C00K C00X 1.387(7) . ?
C00K C011 1.470(7) . ?
C00N C00O 1.384(7) . ?
C00O C015 1.398(7) . ?
C00P C016 1.387(7) . ?
C00Q C00R 1.414(14) . ?
C00Q C01A 1.330(15) . ?
C00R C00V 1.376(15) . ?
C00R C019 1.448(15) . ?
C00S C013 1.376(8) . ?
C00U C011 1.307(8) . ?
C00V C01C 1.354(13) . ?
C00W C015 1.405(7) . ?
C00X C012 1.380(7) . ?
C00Y C018 1.366(8) . ?
C00Z C018 1.386(8) . ?
C010 C016 1.372(7) . ?
C012 C014 1.389(8) . ?
C013 C014 1.399(8) . ?
C014 C01C 1.451(9) . ?
C014 C01D 1.469(14) . ?
C017 C019 1.382(14) . ?
C017 C01B 1.395(14) . ?
C01A C01B 1.404(16) . ?
C01D O0 1.395(15) . ?
C01D C1 1.348(16) . ?
O0 C2 1.43(2) . ?
C1 C3 1.39(2) . ?
C2 C3 1.399(17) . ?
C2 C4 1.35(2) . ?
C3 C0 1.42(2) . ?
C4 C5 1.401(18) . ?
C0 C6 1.38(2) . ?
C5 C6 1.418(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00A O001 C00C 106.1(4) . . ?
C007 O002 C00T 105.8(4) . . ?
C00F O003 C011 106.0(4) . . ?
C01C O004 C00Q 106.8(7) . . ?
C00A C005 C00L 105.2(4) . . ?
C010 C005 C00A 119.1(4) . . ?
C010 C005 C00L 135.7(4) . . ?
C00G C006 C00M 117.6(4) . . ?
C00G C006 C00T 122.7(4) . . ?
C00M C006 C00T 119.6(4) . . ?
O002 C007 C00N 109.9(4) . . ?
C00D C007 O002 126.4(4) . . ?
C00D C007 C00N 123.7(5) . . ?
C00M C008 C00E 121.5(4) . . ?
C00G C009 C00E 120.6(4) . . ?
O001 C00A C005 110.1(4) . . ?
O001 C00A C00H 126.7(4) . . ?
C00H C00A C005 123.2(5) . . ?
C00T C00B C00N 107.4(4) . . ?
O001 C00C C00E 115.5(4) . . ?
C00L C00C O001 110.2(4) . . ?
C00L C00C C00E 134.3(4) . . ?
C00W C00D C007 117.0(5) . . ?
C008 C00E C009 117.6(4) . . ?
C008 C00E C00C 123.5(4) . . ?
C009 C00E C00C 118.9(4) . . ?
O003 C00F C00I 108.6(4) . . ?
C00J C00F O003 128.2(5) . . ?
C00J C00F C00I 123.2(5) . . ?
C009 C00G C006 121.8(4) . . ?
C00P C00H C00A 116.2(4) . . ?
C00F C00I C00U 105.7(5) . . ?
C00Y C00I C00F 118.9(5) . . ?
C00Y C00I C00U 135.4(5) . . ?
C00Z C00J C00F 116.3(5) . . ?
C00S C00K C00X 118.5(5) . . ?
C00S C00K C011 122.9(5) . . ?
C00X C00K C011 118.6(5) . . ?
C00C C00L C005 108.4(4) . . ?
C008 C00M C006 120.9(4) . . ?
C007 C00N C00B 105.0(4) . . ?
C00O C00N C007 118.9(4) . . ?
C00O C00N C00B 136.1(5) . . ?
C00N C00O C015 118.3(5) . . ?
C00H C00P C016 121.4(5) . . ?
O004 C00Q C00R 107.3(11) . . ?
C01A C00Q O004 124.0(11) . . ?
C01A C00Q C00R 128.6(12) . . ?
C00Q C00R C019 113.9(11) . . ?
C00V C00R C00Q 106.9(12) . . ?
C00V C00R C019 139.1(12) . . ?
C013 C00S C00K 120.8(5) . . ?
O002 C00T C006 114.6(4) . . ?
C00B C00T O002 111.9(4) . . ?
C00B C00T C006 133.5(4) . . ?
C011 C00U C00I 108.1(5) . . ?
C01C C00V C00R 109.7(10) . . ?
C00D C00W C015 121.7(5) . . ?
C012 C00X C00K 121.0(5) . . ?
C018 C00Y C00I 118.1(5) . . ?
C00J C00Z C018 121.2(5) . . ?
C016 C010 C005 118.2(4) . . ?
O003 C011 C00K 114.6(5) . . ?
C00U C011 O003 111.6(5) . . ?
C00U C011 C00K 133.8(5) . . ?
C00X C012 C014 120.7(5) . . ?
C00S C013 C014 120.8(5) . . ?
C012 C014 C013 118.1(5) . . ?
C012 C014 C01C 129.0(6) . . ?
C012 C014 C01D 105.3(8) . . ?
C013 C014 C01C 112.9(6) . . ?
C013 C014 C01D 136.5(9) . . ?
C00O C015 C00W 120.3(5) . . ?
C010 C016 C00P 121.9(5) . . ?
C019 C017 C01B 118.8(12) . . ?
C00Y C018 C00Z 122.3(5) . . ?
C017 C019 C00R 120.6(10) . . ?
C00Q C01A C01B 114.0(11) . . ?
C017 C01B C01A 124.0(12) . . ?
O004 C01C C014 110.6(7) . . ?
C00V C01C O004 109.3(7) . . ?
C00V C01C C014 140.1(8) . . ?
O0 C01D C014 108.3(12) . . ?
C1 C01D C014 142.8(14) . . ?
C1 C01D O0 108.9(11) . . ?
C01D O0 C2 105.8(11) . . ?
C01D C1 C3 111.0(14) . . ?
C3 C2 O0 108.4(16) . . ?
C4 C2 O0 120.9(17) . . ?
C4 C2 C3 130.5(19) . . ?
C1 C3 C2 105.9(17) . . ?
C1 C3 C0 141.2(18) . . ?
C2 C3 C0 112.2(18) . . ?
C2 C4 C5 113.4(17) . . ?
C6 C0 C3 122(2) . . ?
C4 C5 C6 122(2) . . ?
C0 C6 C5 119(2) . . ?


_olex2_exptl_crystal_mounting_method 'mounted on loop'
_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 1.396
_oxdiff_exptl_absorpt_empirical_full_min 0.741
