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

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

data_crystal-1
_database_code_depnum_ccdc_archive 'CCDC 2172504'
loop_
_audit_author_name
_audit_author_address
'Yumi Yakiyama'
;Osaka University
Japan
;
_audit_update_record             
;
2022-05-13 deposited with the CCDC.	2022-07-11 downloaded from the CCDC.
;
_audit_creation_date             2022-05-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H10.372, 1.628(F)'
_chemical_formula_sum            'C21 H10.37 F1.63'
_chemical_formula_weight         293.60
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      trigonal
_space_group_IT_number           161
_space_group_name_H-M_alt        'R 3 c'
_space_group_name_Hall           'R 3 -2"c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-y, -x, z+1/2'
'-x+y, y, z+1/2'
'x, x-y, z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'-y+2/3, -x+1/3, z+5/6'
'-x+y+2/3, y+1/3, z+5/6'
'x+2/3, x-y+1/3, z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-y+1/3, -x+2/3, z+7/6'
'-x+y+1/3, y+2/3, z+7/6'
'x+1/3, x-y+2/3, z+7/6'

_cell_length_a                   16.7155(6)
_cell_length_b                   16.7155(6)
_cell_length_c                   7.8787(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1906.44(15)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    5276
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      30.9520
_cell_measurement_theta_min      2.4260
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71824
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             906
_exptl_crystal_size_max          0.174
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_min          0.087
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.891
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6603
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.842
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.013
_diffrn_reflns_theta_min         2.437
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.891
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -6.00  75.00   0.50   22.42    --    5.49  34.00 -79.00  162
  2  ω      1.00  27.00   0.50   22.42    --   -5.42 -99.00 -60.00   52
  3  ω    -26.00  -1.00   0.50   22.42    --   -5.42 -99.00 -90.00   50
  4  ω    -45.00   2.00   0.50   22.42    --    5.49 -90.00 -14.00   94
  5  ω     45.00  70.00   0.50   22.42    --    5.49-161.00 114.00   50
  6  ω    -24.00  16.00   0.50   22.42    --   -5.42 -99.00-180.00   80
  7  ω    -25.00  37.00   0.50   22.42    --    5.49 -99.00 120.00  124
;
_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      -0.0427262000
_diffrn_orient_matrix_UB_12      -0.0328382000
_diffrn_orient_matrix_UB_13      0.0366118000
_diffrn_orient_matrix_UB_21      0.0176833000
_diffrn_orient_matrix_UB_22      -0.0301518000
_diffrn_orient_matrix_UB_23      0.0146988000
_diffrn_orient_matrix_UB_31      0.0161779000
_diffrn_orient_matrix_UB_32      0.0203530000
_diffrn_orient_matrix_UB_33      0.0808779000
_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         0.873
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.793
_reflns_number_gt                1114
_reflns_number_total             1139
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Flack x determined using 502 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     83
_refine_ls_number_reflns         1139
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0330
_refine_ls_restrained_S_all      1.074
_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)+(0.0663P)²+0.3570P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.0927
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Sof(H7A)=Sof(H7B)=1-FVAR(1)
 Sof(F2)=Sof(F1)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
3.b Aromatic/amide H refined with riding coordinates:
 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
C5 C -0.49925(12) -0.89184(12) -0.4828(2) 0.0295(4) Uani 1 1 d . . . . .
H5 H -0.524671 -0.951004 -0.437631 0.035 Uiso 1 1 calc R U . . .
C3 C -0.37903(11) -0.76374(11) -0.6300(2) 0.0242(4) Uani 1 1 d . . . . .
C1 C -0.51577(12) -0.75749(12) -0.5493(3) 0.0267(4) Uani 1 1 d . . . . .
C2 C -0.43020(12) -0.71970(11) -0.6301(2) 0.0245(4) Uani 1 1 d . . . . .
C4 C -0.40990(12) -0.84888(11) -0.5499(2) 0.0270(4) Uani 1 1 d . . . . .
C7 C -0.53423(12) -0.67696(13) -0.5147(3) 0.0300(4) Uani 1 1 d . . . A 1
H7A H -0.553480 -0.677909 -0.398186 0.036 Uiso 0.729(5) 1 calc R U P B 1
H7B H -0.581220 -0.679584 -0.590463 0.036 Uiso 0.729(5) 1 calc R U P B 1
C6 C -0.55179(12) -0.84622(12) -0.4826(2) 0.0301(4) Uani 1 1 d . . . . .
H6 H -0.611129 -0.876035 -0.437383 0.036 Uiso 1 1 calc R U . . .
F2 F -0.5646(3) -0.6767(3) -0.3664(5) 0.0289(11) Uani 0.271(5) 1 d . . P B 2
F1 F -0.6044(3) -0.6852(3) -0.6303(6) 0.0321(12) Uani 0.271(5) 1 d . . P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C5 H5 0.9300 . ?
C5 C4 1.398(2) . ?
C5 C6 1.422(2) . ?
C3 C2 1.431(2) 2_445 ?
C3 C2 1.380(2) . ?
C3 C4 1.399(2) . ?
C1 C2 1.395(2) . ?
C1 C7 1.548(2) . ?
C1 C6 1.395(2) . ?
C4 C7 1.552(2) 2_445 ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C6 H6 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.84(16) . . ?
C6 C5 H5 119.6 . . ?
C2 C3 C2 119.88(18) . 2_445 ?
C2 C3 C4 122.09(15) . . ?
C4 C3 C2 110.92(15) . 2_445 ?
C2 C1 C7 106.96(15) . . ?
C6 C1 C2 116.94(16) . . ?
C6 C1 C7 133.67(19) . . ?
C3 C2 C3 120.12(18) . 3_545 ?
C3 C2 C1 121.80(15) . . ?
C1 C2 C3 110.81(14) . 3_545 ?
C5 C4 C3 116.71(14) . . ?
C5 C4 C7 133.93(16) . 2_445 ?
C3 C4 C7 106.67(14) . 2_445 ?
C1 C7 C4 102.98(13) . 3_545 ?
C1 C7 H7A 111.2 . . ?
C1 C7 H7B 111.2 . . ?
C4 C7 H7A 111.2 3_545 . ?
C4 C7 H7B 111.2 3_545 . ?
H7A C7 H7B 109.1 . . ?
C5 C6 H6 119.5 . . ?
C1 C6 C5 121.06(16) . . ?
C1 C6 H6 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C3 C2 C3 -0.1(3) 2_445 . . 3_545 ?
C2 C3 C2 C1 -147.54(15) 2_445 . . . ?
C2 C3 C4 C5 156.16(16) 2_445 . . . ?
C2 C3 C4 C5 5.8(2) . . . . ?
C2 C3 C4 C7 -158.22(16) . . . 2_445 ?
C2 C3 C4 C7 -7.84(19) 2_445 . . 2_445 ?
C2 C1 C7 C4 -12.3(2) . . . 3_545 ?
C2 C1 C6 C5 6.0(3) . . . . ?
C4 C5 C6 C1 0.0(3) . . . . ?
C4 C3 C2 C3 147.76(14) . . . 3_545 ?
C4 C3 C2 C1 0.3(3) . . . . ?
C7 C1 C2 C3 158.53(15) . . . . ?
C7 C1 C2 C3 8.4(2) . . . 3_545 ?
C7 C1 C6 C5 -153.61(19) . . . . ?
C6 C5 C4 C3 -5.8(3) . . . . ?
C6 C5 C4 C7 152.65(19) . . . 2_445 ?
C6 C1 C2 C3 -156.38(17) . . . 3_545 ?
C6 C1 C2 C3 -6.2(3) . . . . ?
C6 C1 C7 C4 148.8(2) . . . 3_545 ?

_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 1.357
_oxdiff_exptl_absorpt_empirical_full_min 0.688
####################################################################### 
# 
# 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_crystal-7
_database_code_depnum_ccdc_archive 'CCDC 2172506'
loop_
_audit_author_name
_audit_author_address
'Yumi Yakiyama'
;Osaka University
Japan
;
_audit_update_record             
;
2022-05-13 deposited with the CCDC.	2022-07-11 downloaded from the CCDC.
;
_audit_creation_date             2022-05-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H12'
_chemical_formula_sum            'C21 H12'
_chemical_formula_weight         264.31
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      trigonal
_space_group_IT_number           161
_space_group_name_H-M_alt        'R 3 c'
_space_group_name_Hall           'R 3 -2"c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-y, -x, z+1/2'
'-x+y, y, z+1/2'
'x, x-y, z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'-y+2/3, -x+1/3, z+5/6'
'-x+y+2/3, y+1/3, z+5/6'
'x+2/3, x-y+1/3, z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-y+1/3, -x+2/3, z+7/6'
'-x+y+1/3, y+2/3, z+7/6'
'x+1/3, x-y+2/3, z+7/6'

_cell_length_a                   16.5929(7)
_cell_length_b                   16.5929(7)
_cell_length_c                   7.6175(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1816.30(17)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    5309
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      31.0640
_cell_measurement_theta_min      2.4430
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45562
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             828
_exptl_crystal_size_max          0.348
_exptl_crystal_size_mid          0.113
_exptl_crystal_size_min          0.087
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.889
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6223
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.854
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.873
_diffrn_reflns_theta_min         2.455
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.889
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -35.00  -9.00   0.50   10.91    --   -5.26 -91.00-150.00   52
  2  ω    -15.00  29.00   0.50   10.91    --    5.18 -99.00-180.00   88
  3  ω    -23.00  19.00   0.50   10.91    --    5.18 -99.00-120.00   84
  4  ω    -16.00  27.00   0.50   10.91    --   -5.26 -99.00 -60.00   86
  5  ω    -24.00  38.00   0.50   10.91    --    5.18 -99.00 -30.00  124
  6  ω    -77.00   7.00   0.50   10.91    --   -5.26 -79.00  98.00  168
;
_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      -0.0396498000
_diffrn_orient_matrix_UB_12      -0.0175295000
_diffrn_orient_matrix_UB_13      0.0551631000
_diffrn_orient_matrix_UB_21      0.0138183000
_diffrn_orient_matrix_UB_22      0.0459464000
_diffrn_orient_matrix_UB_23      0.0276042000
_diffrn_orient_matrix_UB_31      -0.0259189000
_diffrn_orient_matrix_UB_32      0.0043041000
_diffrn_orient_matrix_UB_33      -0.0697874000
_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         0.905
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.819
_reflns_number_gt                1073
_reflns_number_total             1086
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 501 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     64
_refine_ls_number_reflns         1086
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0360
_refine_ls_restrained_S_all      1.095
_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)+(0.0678P)²+0.7695P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1000
_refine_ls_wR_factor_ref         0.1003
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 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
C2 C -0.71997(12) -0.43095(12) -0.4265(2) 0.0161(4) Uani 1 1 d . . . . .
C3 C -0.76454(12) -0.37947(12) -0.4269(2) 0.0162(4) Uani 1 1 d . . . . .
C1 C -0.75802(12) -0.51764(12) -0.5082(3) 0.0169(4) Uani 1 1 d . . . . .
C5 C -0.89450(12) -0.50144(12) -0.5735(3) 0.0192(4) Uani 1 1 d . . . . .
H5 H -0.954673 -0.527701 -0.617617 0.023 Uiso 1 1 calc R U . . .
C7 C -0.67687(13) -0.53608(12) -0.5453(2) 0.0197(4) Uani 1 1 d . . . . .
H7A H -0.677848 -0.554981 -0.666173 0.024 Uiso 1 1 calc R U . . .
H7B H -0.679382 -0.583656 -0.467794 0.024 Uiso 1 1 calc R U . . .
C6 C -0.84836(12) -0.55460(13) -0.5734(2) 0.0197(4) Uani 1 1 d . . . . .
H6 H -0.879018 -0.614918 -0.617669 0.024 Uiso 1 1 calc R U . . .
C4 C -0.85055(12) -0.41040(13) -0.5080(3) 0.0180(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C2 C3 1.381(2) . ?
C2 C3 1.430(2) 2_455 ?
C2 C1 1.395(2) . ?
C3 C4 1.396(3) . ?
C1 C7 1.549(2) . ?
C1 C6 1.397(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.428(2) . ?
C5 C4 1.400(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C4 1.551(3) 2_455 ?
C6 H6 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 C2 C3 120.18(19) . 2_455 ?
C3 C2 C1 122.02(17) . . ?
C1 C2 C3 110.78(16) . 2_455 ?
C2 C3 C2 119.83(19) . 3_445 ?
C2 C3 C4 122.59(16) . . ?
C4 C3 C2 110.87(17) . 3_445 ?
C2 C1 C7 107.17(15) . . ?
C2 C1 C6 116.39(16) . . ?
C6 C1 C7 134.13(18) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 121.02(16) . . ?
C1 C7 H7A 111.2 . . ?
C1 C7 H7B 111.2 . . ?
C1 C7 C4 102.80(14) . 2_455 ?
H7A C7 H7B 109.1 . . ?
C4 C7 H7A 111.2 2_455 . ?
C4 C7 H7B 111.2 2_455 . ?
C1 C6 C5 121.19(16) . . ?
C1 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C3 C4 C5 116.07(16) . . ?
C3 C4 C7 107.02(15) . 3_445 ?
C5 C4 C7 134.47(18) . 3_445 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C3 C4 C5 157.74(17) 3_445 . . . ?
C2 C3 C4 C5 6.6(3) . . . . ?
C2 C3 C4 C7 -7.1(2) 3_445 . . 3_445 ?
C2 C3 C4 C7 -158.20(17) . . . 3_445 ?
C2 C1 C7 C4 -11.2(2) . . . 2_455 ?
C2 C1 C6 C5 6.8(3) . . . . ?
C3 C2 C3 C2 -0.4(3) 2_455 . . 3_445 ?
C3 C2 C3 C4 148.19(15) 2_455 . . . ?
C3 C2 C1 C7 7.6(2) 2_455 . . . ?
C3 C2 C1 C7 158.24(16) . . . . ?
C3 C2 C1 C6 -157.61(16) 2_455 . . . ?
C3 C2 C1 C6 -7.0(3) . . . . ?
C1 C2 C3 C2 -148.39(15) . . . 3_445 ?
C1 C2 C3 C4 0.2(3) . . . . ?
C7 C1 C6 C5 -153.4(2) . . . . ?
C6 C1 C7 C4 150.3(2) . . . 2_455 ?
C6 C5 C4 C3 -6.7(3) . . . . ?
C6 C5 C4 C7 152.81(19) . . . 3_445 ?
C4 C5 C6 C1 0.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.508
_oxdiff_exptl_absorpt_empirical_full_min 0.422
####################################################################### 
# 
# 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_crystal-8
_database_code_depnum_ccdc_archive 'CCDC 2172507'
loop_
_audit_author_name
_audit_author_address
'Yumi Yakiyama'
;Osaka University
Japan
;
_audit_update_record             
;
2022-05-13 deposited with the CCDC.	2022-07-11 downloaded from the CCDC.
;
_audit_creation_date             2022-05-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H12'
_chemical_formula_sum            'C21 H12'
_chemical_formula_weight         264.31
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      trigonal
_space_group_IT_number           161
_space_group_name_H-M_alt        'R 3 c'
_space_group_name_Hall           'R 3 -2"c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-y, -x, z+1/2'
'-x+y, y, z+1/2'
'x, x-y, z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'-y+2/3, -x+1/3, z+5/6'
'-x+y+2/3, y+1/3, z+5/6'
'x+2/3, x-y+1/3, z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-y+1/3, -x+2/3, z+7/6'
'-x+y+1/3, y+2/3, z+7/6'
'x+1/3, x-y+2/3, z+7/6'

_cell_length_a                   16.5959(7)
_cell_length_b                   16.5959(7)
_cell_length_c                   7.6226(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1818.17(17)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    5715
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      31.0570
_cell_measurement_theta_min      2.4500
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71567
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             828
_exptl_crystal_size_max          0.348
_exptl_crystal_size_mid          0.113
_exptl_crystal_size_min          0.061
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.926
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6699
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.866
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.840
_diffrn_reflns_theta_min         2.454
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.926
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -64.00  14.00   0.50   15.26    --    5.49 -38.00  60.00  156
  2  ω    -14.00  21.00   0.50   15.26    --    5.49 -99.00   0.00   70
  3  ω      5.00  30.00   0.50   15.26    --    5.49-104.00-101.00   50
  4  ω    -23.00  26.00   0.50   15.26    --   -5.42 -99.00-150.00   98
  5  ω    -72.00  -2.00   0.50   15.26    --   -5.42 -74.00 -14.00  140
  6  ω    -24.00  38.00   0.50   15.26    --    5.49 -99.00 150.00  124
;
_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      0.0403265000
_diffrn_orient_matrix_UB_12      0.0297046000
_diffrn_orient_matrix_UB_13      0.0494169000
_diffrn_orient_matrix_UB_21      -0.0099548000
_diffrn_orient_matrix_UB_22      -0.0371457000
_diffrn_orient_matrix_UB_23      0.0583228000
_diffrn_orient_matrix_UB_31      0.0266136000
_diffrn_orient_matrix_UB_32      -0.0131959000
_diffrn_orient_matrix_UB_33      -0.0530390000
_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         0.853
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.804
_reflns_number_gt                1083
_reflns_number_total             1097
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Flack x determined using 495 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.5(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     64
_refine_ls_number_reflns         1097
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0362
_refine_ls_restrained_S_all      1.070
_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)+(0.0712P)²+0.8954P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1021
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C2(H2)
;
_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
C6 C -0.28000(12) -0.56904(13) -0.5735(2) 0.0165(4) Uani 1 1 d . . . . .
C3 C -0.10558(12) -0.49856(12) -0.4266(3) 0.0196(4) Uani 1 1 d . . . . .
H3 H -0.045398 -0.472303 -0.382542 0.023 Uiso 1 1 calc R U . . .
C1 C -0.24200(12) -0.48236(12) -0.4920(3) 0.0170(4) Uani 1 1 d . . . . .
C5 C -0.23549(12) -0.62052(12) -0.5733(2) 0.0164(4) Uani 1 1 d . . . . .
C7 C -0.32317(13) -0.46397(12) -0.4547(2) 0.0199(4) Uani 1 1 d . . . A 1
H7A H -0.320717 -0.416417 -0.532177 0.024 Uiso 1 1 calc R U . A 1
H7B H -0.322174 -0.445089 -0.333950 0.024 Uiso 1 1 calc R U . A 1
C4 C -0.14956(12) -0.58961(13) -0.4920(3) 0.0181(4) Uani 1 1 d . . . . .
C2 C -0.15171(13) -0.44546(13) -0.4265(2) 0.0199(4) Uani 1 1 d . . . . .
H2 H -0.121110 -0.385202 -0.382091 0.024 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C6 C1 1.395(2) . ?
C6 C5 1.381(2) . ?
C6 C5 1.431(2) 2_445 ?
C3 H3 0.9300 . ?
C3 C4 1.401(3) . ?
C3 C2 1.427(2) . ?
C1 C7 1.549(2) . ?
C1 C2 1.397(2) . ?
C5 C4 1.396(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C4 1.552(2) 2_445 ?
C2 H2 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 C6 C5 110.79(16) . 2_445 ?
C5 C6 C1 122.11(17) . . ?
C5 C6 C5 120.14(19) . 2_445 ?
C4 C3 H3 119.5 . . ?
C4 C3 C2 121.00(16) . . ?
C2 C3 H3 119.5 . . ?
C6 C1 C7 107.19(15) . . ?
C6 C1 C2 116.36(16) . . ?
C2 C1 C7 134.09(18) . . ?
C6 C5 C6 119.86(19) . 3_545 ?
C6 C5 C4 122.51(16) . . ?
C4 C5 C6 110.83(17) . 3_545 ?
C1 C7 H7A 111.2 . . ?
C1 C7 H7B 111.2 . . ?
C1 C7 C4 102.76(14) . 2_445 ?
H7A C7 H7B 109.1 . . ?
C4 C7 H7A 111.2 2_445 . ?
C4 C7 H7B 111.2 2_445 . ?
C3 C4 C7 134.42(17) . 3_545 ?
C5 C4 C3 116.10(16) . . ?
C5 C4 C7 107.06(15) . 3_545 ?
C3 C2 H2 119.4 . . ?
C1 C2 C3 121.20(16) . . ?
C1 C2 H2 119.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C7 C4 11.1(2) . . . 2_445 ?
C6 C1 C2 C3 -6.6(3) . . . . ?
C6 C5 C4 C3 -6.8(3) . . . . ?
C6 C5 C4 C3 -157.71(17) 3_545 . . . ?
C6 C5 C4 C7 158.17(16) . . . 3_545 ?
C6 C5 C4 C7 7.22(19) 3_545 . . 3_545 ?
C1 C6 C5 C6 148.35(15) . . . 3_545 ?
C1 C6 C5 C4 -0.1(3) . . . . ?
C5 C6 C1 C7 -158.23(16) . . . . ?
C5 C6 C1 C7 -7.5(2) 2_445 . . . ?
C5 C6 C1 C2 157.55(16) 2_445 . . . ?
C5 C6 C1 C2 6.8(3) . . . . ?
C5 C6 C5 C6 0.3(3) 2_445 . . 3_545 ?
C5 C6 C5 C4 -148.18(15) 2_445 . . . ?
C7 C1 C2 C3 153.33(19) . . . . ?
C4 C3 C2 C1 -0.2(3) . . . . ?
C2 C3 C4 C5 6.8(3) . . . . ?
C2 C3 C4 C7 -152.84(19) . . . 3_545 ?
C2 C1 C7 C4 -150.1(2) . . . 2_445 ?

_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 1.377
_oxdiff_exptl_absorpt_empirical_full_min 0.627
####################################################################### 
# 
# 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_crystal-15
_database_code_depnum_ccdc_archive 'CCDC 2172514'
loop_
_audit_author_name
_audit_author_address
'Yumi Yakiyama'
;Osaka University
Japan
;
_audit_update_record             
;
2022-05-13 deposited with the CCDC.	2022-07-11 downloaded from the CCDC.
;
_audit_creation_date             2022-05-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H11.781, 0.219(F)'
_chemical_formula_sum            'C21 H11.78 F0.22'
_chemical_formula_weight         268.23
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      trigonal
_space_group_IT_number           161
_space_group_name_H-M_alt        'R 3 c'
_space_group_name_Hall           'R 3 -2"c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-y, -x, z+1/2'
'-x+y, y, z+1/2'
'x, x-y, z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'-y+2/3, -x+1/3, z+5/6'
'-x+y+2/3, y+1/3, z+5/6'
'x+2/3, x-y+1/3, z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-y+1/3, -x+2/3, z+7/6'
'-x+y+1/3, y+2/3, z+7/6'
'x+1/3, x-y+2/3, z+7/6'

_cell_length_a                   16.6264(4)
_cell_length_b                   16.6264(4)
_cell_length_c                   7.6483(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1831.01(10)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    2059
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      75.5780
_cell_measurement_theta_min      5.3380
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.657
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49272
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             838
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.056
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2221
_diffrn_reflns_point_group_measured_fraction_full 0.909
_diffrn_reflns_point_group_measured_fraction_max 0.892
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.056
_diffrn_reflns_theta_min         5.321
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     79.00 111.00   0.50    0.63    --   70.50  90.00  33.00   64
  2  ω    -55.00 -30.00   0.50    0.63    -- -106.00  19.00 120.00   50
  3  ω    -75.00 -49.00   0.50    0.63    -- -106.00 122.00  19.00   52
  4  ω   -113.00 -76.00   0.50    0.63    -- -106.00 122.00  19.00   74
  5  ω   -117.00 -33.00   0.50    0.63    -- -106.00  58.00  41.00  168
  6  ω   -105.00 -54.00   0.50    0.63    -- -106.00  19.00  30.00  102
  7  ω   -119.00 -61.00   0.50    0.63    -- -106.00  19.00 120.00  116
  8  ω   -118.00 -93.00   0.50    0.63    -- -106.00 -37.00 120.00   50
  9  ω   -148.00 -95.00   0.50    0.63    -- -106.00 -19.00 150.00  106
 10  ω   -177.00-151.00   0.50    0.63    -- -106.00 -37.00 120.00   52
 11  ω   -136.00-101.00   0.50    0.63    -- -106.00  90.00  33.00   70
 12  ω   -116.00 -54.00   0.50    0.16    --  -46.62-160.00-125.00  124
;
_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      -0.0626728000
_diffrn_orient_matrix_UB_12      0.0366135000
_diffrn_orient_matrix_UB_13      -0.0696996000
_diffrn_orient_matrix_UB_21      0.0101743000
_diffrn_orient_matrix_UB_22      -0.0284192000
_diffrn_orient_matrix_UB_23      -0.1868368000
_diffrn_orient_matrix_UB_31      -0.0860119000
_diffrn_orient_matrix_UB_32      -0.0964630000
_diffrn_orient_matrix_UB_33      0.0285067000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.775
_reflns_Friedel_fraction_full    0.816
_reflns_Friedel_fraction_max     0.788
_reflns_number_gt                761
_reflns_number_total             765
_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 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details 
;
 Flack x determined using 328 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     73
_refine_ls_number_reflns         765
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0401
_refine_ls_restrained_S_all      1.153
_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)+(0.0824P)²+0.5317P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1131
_refine_ls_wR_factor_ref         0.1132
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Sof(F1)=Sof(F2)=1-FVAR(1)
 Sof(H7A)=Sof(H7B)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C1(H1)
;
_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
C5 C -0.28027(16) -0.56924(16) -0.5733(3) 0.0210(6) Uani 1 1 d . . . . .
C2 C -0.10597(16) -0.49875(16) -0.4271(4) 0.0248(6) Uani 1 1 d . . . . .
H2 H -0.045847 -0.472492 -0.383483 0.030 Uiso 1 1 calc R U . . .
C4 C -0.23553(16) -0.62070(17) -0.5732(3) 0.0208(6) Uani 1 1 d . . . . .
C6 C -0.24199(16) -0.48261(16) -0.4924(4) 0.0218(6) Uani 1 1 d . . . . .
C3 C -0.14977(16) -0.58954(18) -0.4921(4) 0.0229(6) Uani 1 1 d . . . . .
C7 C -0.32324(17) -0.46421(17) -0.4552(3) 0.0243(6) Uani 1 1 d . . . A 1
H7A H -0.320841 -0.416813 -0.532528 0.029 Uiso 0.964(7) 1 calc R U P B 1
H7B H -0.322205 -0.445263 -0.334885 0.029 Uiso 0.964(7) 1 calc R U P B 1
C1 C -0.15204(17) -0.44567(17) -0.4267(3) 0.0244(6) Uani 1 1 d . . . . .
H1 H -0.121641 -0.385615 -0.381939 0.029 Uiso 1 1 calc R U . . .
F1 F -0.325(3) -0.435(3) -0.303(6) 0.030(13) Uiso 0.036(7) 1 d . . P B 2
F2 F -0.313(3) -0.387(3) -0.576(6) 0.033(14) Uiso 0.036(7) 1 d . . P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C5 C4 1.386(3) . ?
C5 C4 1.427(3) 2_445 ?
C5 C6 1.395(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.399(4) . ?
C2 C1 1.429(3) . ?
C4 C3 1.395(3) . ?
C6 C7 1.553(3) . ?
C6 C1 1.396(3) . ?
C3 C7 1.554(3) 3_545 ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C1 H1 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 C5 C4 120.3(2) . 2_445 ?
C4 C5 C6 121.9(2) . . ?
C6 C5 C4 110.9(2) . 2_445 ?
C3 C2 H2 119.4 . . ?
C3 C2 C1 121.1(2) . . ?
C1 C2 H2 119.4 . . ?
C5 C4 C5 119.7(2) . 3_545 ?
C5 C4 C3 122.4(2) . . ?
C3 C4 C5 111.1(2) . 3_545 ?
C5 C6 C7 107.0(2) . . ?
C5 C6 C1 116.7(2) . . ?
C1 C6 C7 133.9(3) . . ?
C2 C3 C7 134.5(2) . 3_545 ?
C4 C3 C2 116.3(2) . . ?
C4 C3 C7 106.8(2) . 3_545 ?
C6 C7 C3 102.78(18) . 2_445 ?
C6 C7 H7A 111.2 . . ?
C6 C7 H7B 111.2 . . ?
C3 C7 H7A 111.2 2_445 . ?
C3 C7 H7B 111.2 2_445 . ?
H7A C7 H7B 109.1 . . ?
C2 C1 H1 119.5 . . ?
C6 C1 C2 121.0(2) . . ?
C6 C1 H1 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 C4 C3 C2 -157.6(2) 3_545 . . . ?
C5 C4 C3 C2 -6.9(4) . . . . ?
C5 C4 C3 C7 7.4(3) 3_545 . . 3_545 ?
C5 C4 C3 C7 158.2(2) . . . 3_545 ?
C5 C6 C7 C3 11.1(3) . . . 2_445 ?
C5 C6 C1 C2 -6.2(4) . . . . ?
C4 C5 C4 C5 0.2(5) 2_445 . . 3_545 ?
C4 C5 C4 C3 -148.2(2) 2_445 . . . ?
C4 C5 C6 C7 -158.4(2) . . . . ?
C4 C5 C6 C7 -7.4(3) 2_445 . . . ?
C4 C5 C6 C1 6.4(4) . . . . ?
C4 C5 C6 C1 157.4(2) 2_445 . . . ?
C6 C5 C4 C5 148.5(2) . . . 3_545 ?
C6 C5 C4 C3 0.2(4) . . . . ?
C3 C2 C1 C6 -0.5(4) . . . . ?
C7 C6 C1 C2 153.5(3) . . . . ?
C1 C2 C3 C4 6.9(4) . . . . ?
C1 C2 C3 C7 -152.8(3) . . . 3_545 ?
C1 C6 C7 C3 -149.9(3) . . . 2_445 ?

_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 1.770
_oxdiff_exptl_absorpt_empirical_full_min 0.509
####################################################################### 
# 
# 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_crystal-2
_database_code_depnum_ccdc_archive 'CCDC 2172505'
loop_
_audit_author_name
_audit_author_address
'Yumi Yakiyama'
;Osaka University
Japan
;
_audit_update_record             
;
2022-05-13 deposited with the CCDC.	2022-07-11 downloaded from the CCDC.
;
_audit_creation_date             2022-05-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H3.448, 0.552(F)'
_chemical_formula_sum            'C7 H3.45 F0.55'
_chemical_formula_weight         98.03
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      trigonal
_space_group_IT_number           161
_space_group_name_H-M_alt        'R 3 c'
_space_group_name_Hall           'R 3 -2"c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-y, -x, z+1/2'
'-x+y, y, z+1/2'
'x, x-y, z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'-y+2/3, -x+1/3, z+5/6'
'-x+y+2/3, y+1/3, z+5/6'
'x+2/3, x-y+1/3, z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-y+1/3, -x+2/3, z+7/6'
'-x+y+1/3, y+2/3, z+7/6'
'x+1/3, x-y+2/3, z+7/6'

_cell_length_a                   16.7139(6)
_cell_length_b                   16.7139(6)
_cell_length_c                   7.8744(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1905.04(15)
_cell_formula_units_Z            18
_cell_measurement_reflns_used    5696
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      30.8110
_cell_measurement_theta_min      2.4290
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54245
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             907
_exptl_crystal_size_max          0.191
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.087
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.912
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7122
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.853
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.744
_diffrn_reflns_theta_min         2.437
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.912
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -2.00  57.00   0.50   18.30    --    5.18  41.00 -14.00  118
  2  ω    -26.00  25.00   0.50   18.30    --    5.18 -99.00 150.00  102
  3  ω     -2.00  29.00   0.50   18.30    --    5.18 -99.00  30.00   62
  4  ω    -23.00  28.00   0.50   18.30    --   -5.26 -99.00-120.00  102
  5  ω     32.00  76.00   0.50   18.30    --    5.18-166.00-176.00   88
  6  ω    -25.00  33.00   0.50   18.30    --    5.18 -99.00-180.00  116
  7  ω    -73.00 -37.00   0.50   18.30    --   -5.26 166.00-155.00   72
;
_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      -0.0469007000
_diffrn_orient_matrix_UB_12      -0.0111734000
_diffrn_orient_matrix_UB_13      0.0010462000
_diffrn_orient_matrix_UB_21      -0.0117413000
_diffrn_orient_matrix_UB_22      -0.0405752000
_diffrn_orient_matrix_UB_23      0.0471800000
_diffrn_orient_matrix_UB_31      0.0079194000
_diffrn_orient_matrix_UB_32      0.0251420000
_diffrn_orient_matrix_UB_33      0.0766564000
_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         0.853
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.792
_reflns_number_gt                1118
_reflns_number_total             1134
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 
;
 Flack x determined using 493 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.6(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     83
_refine_ls_number_reflns         1134
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0336
_refine_ls_restrained_S_all      1.042
_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)+(0.0696P)²+0.3976P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0930
_refine_ls_wR_factor_ref         0.0935
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Sof(H7A)=Sof(H7B)=1-FVAR(1)
 Sof(F2)=Sof(F1)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
3.b Aromatic/amide H refined with riding coordinates:
 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
C5 C 0.50084(12) 0.10812(12) 0.5172(3) 0.0297(4) Uani 1 1 d . . . . .
H5 H 0.475392 0.048904 0.562143 0.036 Uiso 1 1 calc R U . . .
C1 C 0.48422(12) 0.24245(12) 0.4507(3) 0.0266(4) Uani 1 1 d . . . . .
C3 C 0.62095(11) 0.23626(11) 0.3702(2) 0.0242(4) Uani 1 1 d . . . . .
C2 C 0.56979(12) 0.28023(11) 0.3700(2) 0.0246(4) Uani 1 1 d . . . . .
C4 C 0.59014(12) 0.15112(11) 0.4502(2) 0.0270(4) Uani 1 1 d . . . . .
C7 C 0.46590(12) 0.32307(13) 0.4852(3) 0.0298(4) Uani 1 1 d . . . A 1
H7A H 0.446577 0.322100 0.601665 0.036 Uiso 0.724(5) 1 calc R U P B 1
H7B H 0.418952 0.320470 0.409248 0.036 Uiso 0.724(5) 1 calc R U P B 1
C6 C 0.44828(12) 0.15385(12) 0.5175(2) 0.0301(4) Uani 1 1 d . . . . .
H6 H 0.388994 0.124095 0.563008 0.036 Uiso 1 1 calc R U . . .
F2 F 0.4355(2) 0.3234(3) 0.6338(5) 0.0287(11) Uani 0.276(5) 1 d . . P B 2
F1 F 0.3959(3) 0.3150(3) 0.3698(5) 0.0318(11) Uani 0.276(5) 1 d . . P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C5 H5 0.9300 . ?
C5 C4 1.396(2) . ?
C5 C6 1.424(2) . ?
C1 C2 1.394(2) . ?
C1 C7 1.548(2) . ?
C1 C6 1.393(2) . ?
C3 C2 1.432(2) 2_655 ?
C3 C2 1.378(2) . ?
C3 C4 1.398(2) . ?
C4 C7 1.549(2) 2_655 ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C6 H6 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.79(15) . . ?
C6 C5 H5 119.6 . . ?
C2 C1 C7 106.88(15) . . ?
C6 C1 C2 116.92(16) . . ?
C6 C1 C7 133.73(19) . . ?
C2 C3 C2 119.90(18) . 2_655 ?
C2 C3 C4 122.15(15) . . ?
C4 C3 C2 110.91(15) . 2_655 ?
C1 C2 C3 110.79(15) . 3_665 ?
C3 C2 C1 121.83(15) . . ?
C3 C2 C3 120.10(18) . 3_665 ?
C5 C4 C3 116.69(14) . . ?
C5 C4 C7 134.00(16) . 2_655 ?
C3 C4 C7 106.63(14) . 2_655 ?
C1 C7 C4 103.13(13) . 3_665 ?
C1 C7 H7A 111.1 . . ?
C1 C7 H7B 111.1 . . ?
C4 C7 H7A 111.1 3_665 . ?
C4 C7 H7B 111.1 3_665 . ?
H7A C7 H7B 109.1 . . ?
C5 C6 H6 119.5 . . ?
C1 C6 C5 121.07(16) . . ?
C1 C6 H6 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C1 C7 C4 -12.3(2) . . . 3_665 ?
C2 C1 C6 C5 5.8(3) . . . . ?
C2 C3 C2 C1 -147.63(15) 2_655 . . . ?
C2 C3 C2 C3 -0.2(3) 2_655 . . 3_665 ?
C2 C3 C4 C5 5.7(2) . . . . ?
C2 C3 C4 C5 156.25(16) 2_655 . . . ?
C2 C3 C4 C7 -158.32(16) . . . 2_655 ?
C2 C3 C4 C7 -7.81(19) 2_655 . . 2_655 ?
C4 C5 C6 C1 0.2(3) . . . . ?
C4 C3 C2 C1 0.3(3) . . . . ?
C4 C3 C2 C3 147.77(14) . . . 3_665 ?
C7 C1 C2 C3 158.49(15) . . . . ?
C7 C1 C2 C3 8.4(2) . . . 3_665 ?
C7 C1 C6 C5 -153.63(19) . . . . ?
C6 C5 C4 C3 -5.9(3) . . . . ?
C6 C5 C4 C7 152.62(19) . . . 2_655 ?
C6 C1 C2 C3 -156.26(17) . . . 3_665 ?
C6 C1 C2 C3 -6.1(3) . . . . ?
C6 C1 C7 C4 148.6(2) . . . 3_665 ?

_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 1.547
_oxdiff_exptl_absorpt_empirical_full_min 0.481
####################################################################### 
# 
# 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_crystal-3
_database_code_depnum_ccdc_archive 'CCDC 2172509'
loop_
_audit_author_name
_audit_author_address
'Yumi Yakiyama'
;Osaka University
Japan
;
_audit_update_record             
;
2022-05-13 deposited with the CCDC.	2022-07-11 downloaded from the CCDC.
;
_audit_creation_date             2022-05-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H3.527, 0.473(F)'
_chemical_formula_sum            'C7 H3.53 F0.47'
_chemical_formula_weight         96.61
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      trigonal
_space_group_IT_number           161
_space_group_name_H-M_alt        'R 3 c'
_space_group_name_Hall           'R 3 -2"c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-y, -x, z+1/2'
'-x+y, y, z+1/2'
'x, x-y, z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'-y+2/3, -x+1/3, z+5/6'
'-x+y+2/3, y+1/3, z+5/6'
'x+2/3, x-y+1/3, z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-y+1/3, -x+2/3, z+7/6'
'-x+y+1/3, y+2/3, z+7/6'
'x+1/3, x-y+2/3, z+7/6'

_cell_length_a                   16.7002(5)
_cell_length_b                   16.7002(5)
_cell_length_c                   7.8414(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1893.95(13)
_cell_formula_units_Z            18
_cell_measurement_reflns_used    5211
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      30.4130
_cell_measurement_theta_min      4.1840
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44160
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.565
_exptl_crystal_size_mid          0.191
_exptl_crystal_size_min          0.087
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.907
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7083
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.842
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.767
_diffrn_reflns_theta_min         2.439
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.907
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -71.00   1.00   0.50   15.27    --   -5.18 -35.00-121.00  144
  2  ω    -16.00  16.00   0.50   15.27    --   -5.18  37.00-150.00   64
  3  ω     20.00  67.00   0.50   15.27    --   -5.18  37.00-150.00   94
  4  ω    -21.00   5.00   0.50   15.27    --    5.34  87.00-166.00   52
  5  ω    -25.00  22.00   0.50   15.27    --   -5.18 -99.00  30.00   94
  6  ω    -25.00  23.00   0.50   15.27    --    5.34 -99.00  60.00   96
  7  ω    -25.00  39.00   0.50   15.27    --    5.34 -99.00-150.00  128
;
_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      -0.0305877000
_diffrn_orient_matrix_UB_12      -0.0291136000
_diffrn_orient_matrix_UB_13      0.0643392000
_diffrn_orient_matrix_UB_21      0.0314625000
_diffrn_orient_matrix_UB_22      0.0287031000
_diffrn_orient_matrix_UB_23      0.0635786000
_diffrn_orient_matrix_UB_31      -0.0218797000
_diffrn_orient_matrix_UB_32      0.0270691000
_diffrn_orient_matrix_UB_33      0.0016916000
_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         0.840
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.776
_reflns_number_gt                1084
_reflns_number_total             1113
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 482 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     83
_refine_ls_number_reflns         1113
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0342
_refine_ls_restrained_S_all      1.034
_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)+(0.0670P)²+0.5906P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0936
_refine_ls_wR_factor_ref         0.0948
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Sof(H7A)=Sof(H7B)=1-FVAR(1)
 Sof(F2)=Sof(F1)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
3.b Aromatic/amide H refined with riding coordinates:
 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
C5 C -0.89225(12) -0.49954(13) -0.5732(3) 0.0294(4) Uani 1 1 d . . . . .
H5 H -0.951619 -0.525108 -0.617925 0.035 Uiso 1 1 calc R U . . .
C3 C -0.76386(11) -0.37911(12) -0.4264(2) 0.0244(4) Uani 1 1 d . . . . .
C1 C -0.75754(13) -0.51602(12) -0.5071(3) 0.0265(4) Uani 1 1 d . . . . .
C2 C -0.71973(11) -0.43031(13) -0.4263(2) 0.0246(4) Uani 1 1 d . . . . .
C7 C -0.67691(14) -0.53439(12) -0.5421(3) 0.0299(4) Uani 1 1 d . . . A 1
H7A H -0.677822 -0.553532 -0.659182 0.036 Uiso 0.764(5) 1 calc R U P B 1
H7B H -0.679523 -0.581483 -0.466102 0.036 Uiso 0.764(5) 1 calc R U P B 1
C4 C -0.84905(11) -0.40997(12) -0.5064(3) 0.0268(4) Uani 1 1 d . . . . .
C6 C -0.84642(13) -0.55216(13) -0.5736(3) 0.0297(4) Uani 1 1 d . . . . .
H6 H -0.876303 -0.611592 -0.618857 0.036 Uiso 1 1 calc R U . . .
F2 F -0.6766(3) -0.5646(3) -0.6903(6) 0.0282(13) Uani 0.236(5) 1 d . . P B 2
F1 F -0.6854(3) -0.6049(3) -0.4250(7) 0.0321(14) Uani 0.236(5) 1 d . . P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C5 H5 0.9300 . ?
C5 C4 1.397(3) . ?
C5 C6 1.425(3) . ?
C3 C2 1.431(2) 3_445 ?
C3 C2 1.380(2) . ?
C3 C4 1.396(2) . ?
C1 C2 1.395(2) . ?
C1 C7 1.548(2) . ?
C1 C6 1.394(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C4 1.552(3) 2_455 ?
C6 H6 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.78(16) . . ?
C6 C5 H5 119.6 . . ?
C2 C3 C2 119.87(19) . 3_445 ?
C2 C3 C4 122.19(16) . . ?
C4 C3 C2 110.93(16) . 3_445 ?
C2 C1 C7 106.95(16) . . ?
C6 C1 C2 116.87(16) . . ?
C6 C1 C7 133.76(19) . . ?
C3 C2 C3 120.12(19) . 2_455 ?
C3 C2 C1 121.83(16) . . ?
C1 C2 C3 110.81(15) . 2_455 ?
C1 C7 H7A 111.2 . . ?
C1 C7 H7B 111.2 . . ?
C1 C7 C4 102.99(13) . 2_455 ?
H7A C7 H7B 109.1 . . ?
C4 C7 H7A 111.2 2_455 . ?
C4 C7 H7B 111.2 2_455 . ?
C5 C4 C7 133.93(17) . 3_445 ?
C3 C4 C5 116.67(15) . . ?
C3 C4 C7 106.73(15) . 3_445 ?
C5 C6 H6 119.5 . . ?
C1 C6 C5 121.08(17) . . ?
C1 C6 H6 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C3 C2 C3 -0.2(3) 3_445 . . 2_455 ?
C2 C3 C2 C1 -147.70(16) 3_445 . . . ?
C2 C3 C4 C5 156.46(17) 3_445 . . . ?
C2 C3 C4 C5 5.9(3) . . . . ?
C2 C3 C4 C7 -158.21(17) . . . 3_445 ?
C2 C3 C4 C7 -7.6(2) 3_445 . . 3_445 ?
C2 C1 C7 C4 -12.1(2) . . . 2_455 ?
C2 C1 C6 C5 6.0(3) . . . . ?
C7 C1 C2 C3 158.47(16) . . . . ?
C7 C1 C2 C3 8.2(2) . . . 2_455 ?
C7 C1 C6 C5 -153.7(2) . . . . ?
C4 C5 C6 C1 0.2(3) . . . . ?
C4 C3 C2 C3 147.88(15) . . . 2_455 ?
C4 C3 C2 C1 0.3(3) . . . . ?
C6 C5 C4 C3 -6.1(3) . . . . ?
C6 C5 C4 C7 152.6(2) . . . 3_445 ?
C6 C1 C2 C3 -156.53(17) . . . 2_455 ?
C6 C1 C2 C3 -6.3(3) . . . . ?
C6 C1 C7 C4 149.0(2) . . . 2_455 ?

_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 2.143
_oxdiff_exptl_absorpt_empirical_full_min 0.368
####################################################################### 
# 
# 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_crystal-9
_database_code_depnum_ccdc_archive 'CCDC 2172516'
loop_
_audit_author_name
_audit_author_address
'Yumi Yakiyama'
;Osaka University
Japan
;
_audit_update_record             
;
2022-05-13 deposited with the CCDC.	2022-07-11 downloaded from the CCDC.
;
_audit_creation_date             2022-05-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H10.417, 1.583(F)'
_chemical_formula_sum            'C21 H10.42 F1.58'
_chemical_formula_weight         292.79
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      trigonal
_space_group_IT_number           161
_space_group_name_H-M_alt        'R 3 c'
_space_group_name_Hall           'R 3 -2"c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-y, -x, z+1/2'
'-x+y, y, z+1/2'
'x, x-y, z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'-y+2/3, -x+1/3, z+5/6'
'-x+y+2/3, y+1/3, z+5/6'
'x+2/3, x-y+1/3, z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-y+1/3, -x+2/3, z+7/6'
'-x+y+1/3, y+2/3, z+7/6'
'x+1/3, x-y+2/3, z+7/6'

_cell_length_a                   16.7553(12)
_cell_length_b                   16.7553(12)
_cell_length_c                   7.9305(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1928.1(3)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    1637
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      74.8610
_cell_measurement_theta_min      5.2840
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.835
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35232
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1262
_diffrn_reflns_av_unetI/netI     0.0496
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2222
_diffrn_reflns_point_group_measured_fraction_full 0.921
_diffrn_reflns_point_group_measured_fraction_max 0.903
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.048
_diffrn_reflns_theta_min         5.280
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'CCD plate'
_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    -67.00  -5.00   0.50    0.76    --  -46.62  73.00-143.00  124
  2  ω     71.00  96.00   0.50    0.76    --   46.62 125.00-120.00   50
  3  ω     73.00 116.00   0.50    0.76    --   46.62 125.00 120.00   86
  4  ω    -78.00 -39.00   0.50    3.06    -- -106.00  67.00  91.00   78
  5  ω   -100.00 -52.00   0.50    3.06    -- -106.00  94.00 -46.00   96
  6  ω   -102.00 -66.00   0.50    3.06    -- -106.00 125.00  30.00   72
  7  ω   -105.00 -33.00   0.50    3.06    -- -106.00 125.00  90.00  144
  8  ω   -126.00 -87.00   0.50    3.06    -- -106.00  67.00  91.00   78
  9  ω   -129.00 -91.00   0.50    3.06    -- -106.00 -19.00   0.00   76
 10  ω   -138.00-112.00   0.50    3.06    -- -106.00 -52.00 -75.00   52
 11  ω   -168.00-142.00   0.50    3.06    -- -106.00 -52.00 -75.00   52
 12  ω   -175.00-134.00   0.50    3.06    -- -106.00 -19.00   0.00   82
 13  ω   -174.00-113.00   0.50    3.06    -- -106.00 -67.00 -42.00  122
;
_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      -0.0520925000
_diffrn_orient_matrix_UB_12      0.0203814000
_diffrn_orient_matrix_UB_13      -0.1380075000
_diffrn_orient_matrix_UB_21      0.0349126000
_diffrn_orient_matrix_UB_22      0.0967636000
_diffrn_orient_matrix_UB_23      0.0748119000
_diffrn_orient_matrix_UB_31      0.0856157000
_diffrn_orient_matrix_UB_32      0.0386039000
_diffrn_orient_matrix_UB_33      -0.1144045000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.786
_reflns_Friedel_fraction_full    0.840
_reflns_Friedel_fraction_max     0.804
_reflns_number_gt                753
_reflns_number_total             802
_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 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.083
_refine_ls_abs_structure_details 
;
 Flack x determined using 296 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.8(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     83
_refine_ls_number_reflns         802
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0762
_refine_ls_restrained_S_all      1.141
_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)+(0.1781P)²+1.5638P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2157
_refine_ls_wR_factor_ref         0.2477
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Sof(H7A)=Sof(H7B)=1-FVAR(1)
 Sof(F1)=Sof(F2)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.5752(4) -0.4233(4) -0.5532(10) 0.0420(15) Uani 1 1 d . . . . .
C2 C -0.6288(4) -0.5131(4) -0.4853(8) 0.0445(15) Uani 1 1 d . . . . .
H2 H -0.599658 -0.543007 -0.439508 0.053 Uiso 1 1 calc R U . . .
C3 C -0.7260(4) -0.5576(4) -0.4865(9) 0.0441(14) Uani 1 1 d . . . . .
H3 H -0.759906 -0.616714 -0.441979 0.053 Uiso 1 1 calc R U . . .
C4 C -0.7720(4) -0.5150(4) -0.5531(8) 0.0417(15) Uani 1 1 d . . . . .
C5 C -0.7178(4) -0.4300(3) -0.6315(8) 0.0381(15) Uani 1 1 d . . . . .
C6 C -0.6230(4) -0.3867(4) -0.6315(7) 0.0384(13) Uani 1 1 d . . . . .
C7 C -0.4777(4) -0.3443(5) -0.5190(9) 0.0461(15) Uani 1 1 d . . . A 1
H7A H -0.433536 -0.347131 -0.594367 0.055 Uiso 0.736(15) 1 calc R U P B 1
H7B H -0.459522 -0.345650 -0.403331 0.055 Uiso 0.736(15) 1 calc R U P B 1
F1 F -0.4137(8) -0.3512(9) -0.6348(19) 0.048(4) Uani 0.264(15) 1 d . . P B 2
F2 F -0.4451(9) -0.3442(8) -0.3691(16) 0.041(4) Uani 0.264(15) 1 d . . P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.418(8) . ?
C1 C6 1.376(9) . ?
C1 C7 1.527(9) . ?
C2 H2 0.9300 . ?
C2 C3 1.412(8) . ?
C3 H3 0.9300 . ?
C3 C4 1.392(8) . ?
C4 C5 1.395(8) . ?
C4 C7 1.551(8) 3_445 ?
C5 C6 1.436(7) 3_445 ?
C5 C6 1.377(7) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C7 133.4(7) . . ?
C6 C1 C2 116.3(6) . . ?
C6 C1 C7 107.7(5) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.6(6) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 119.3 . . ?
C4 C3 C2 121.4(5) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 C5 116.6(5) . . ?
C3 C4 C7 134.4(6) . 3_445 ?
C5 C4 C7 106.1(5) . 3_445 ?
C4 C5 C6 110.7(5) . 3_445 ?
C6 C5 C4 121.9(5) . . ?
C6 C5 C6 120.5(6) . 3_445 ?
C1 C6 C5 122.7(5) . . ?
C1 C6 C5 110.6(5) . 2_455 ?
C5 C6 C5 119.5(6) . 2_455 ?
C1 C7 C4 103.3(4) . 2_455 ?
C1 C7 H7A 111.1 . . ?
C1 C7 H7B 111.1 . . ?
C4 C7 H7A 111.1 2_455 . ?
C4 C7 H7B 111.1 2_455 . ?
H7A C7 H7B 109.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -0.4(10) . . . . ?
C2 C1 C6 C5 156.0(6) . . . 2_455 ?
C2 C1 C6 C5 6.0(10) . . . . ?
C2 C1 C7 C4 -148.4(7) . . . 2_455 ?
C2 C3 C4 C5 5.5(9) . . . . ?
C2 C3 C4 C7 -152.2(7) . . . 3_445 ?
C3 C4 C5 C6 -156.2(5) . . . 3_445 ?
C3 C4 C5 C6 -5.1(8) . . . . ?
C4 C5 C6 C1 -0.8(9) . . . . ?
C4 C5 C6 C5 -148.3(5) . . . 2_455 ?
C6 C1 C2 C3 -5.4(10) . . . . ?
C6 C1 C7 C4 12.1(8) . . . 2_455 ?
C6 C5 C6 C1 147.6(5) 3_445 . . . ?
C6 C5 C6 C5 0.0(10) 3_445 . . 2_455 ?
C7 C1 C2 C3 153.8(6) . . . . ?
C7 C1 C6 C5 -8.2(7) . . . 2_455 ?
C7 C1 C6 C5 -158.3(5) . . . . ?
C7 C4 C5 C6 158.6(5) 3_445 . . . ?
C7 C4 C5 C6 7.5(7) 3_445 . . 3_445 ?

_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 2.627
_oxdiff_exptl_absorpt_empirical_full_min 0.305
####################################################################### 
# 
# 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_crystal-13
_database_code_depnum_ccdc_archive 'CCDC 2172517'
loop_
_audit_author_name
_audit_author_address
'Yumi Yakiyama'
;Osaka University
Japan
;
_audit_update_record             
;
2022-05-13 deposited with the CCDC.	2022-07-11 downloaded from the CCDC.
;
_audit_creation_date             2022-05-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H11.068, 0.932(F)'
_chemical_formula_sum            'C21 H11.07 F0.93'
_chemical_formula_weight         281.07
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      trigonal
_space_group_IT_number           161
_space_group_name_H-M_alt        'R 3 c'
_space_group_name_Hall           'R 3 -2"c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-y, -x, z+1/2'
'-x+y, y, z+1/2'
'x, x-y, z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'-y+2/3, -x+1/3, z+5/6'
'-x+y+2/3, y+1/3, z+5/6'
'x+2/3, x-y+1/3, z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-y+1/3, -x+2/3, z+7/6'
'-x+y+1/3, y+2/3, z+7/6'
'x+1/3, x-y+2/3, z+7/6'

_cell_length_a                   16.6836(6)
_cell_length_b                   16.6836(6)
_cell_length_c                   7.7867(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1877.00(15)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    1495
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      74.5960
_cell_measurement_theta_min      5.2890
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.754
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54800
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             873
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.057
_exptl_crystal_size_min          0.029
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            2189
_diffrn_reflns_point_group_measured_fraction_full 0.647
_diffrn_reflns_point_group_measured_fraction_max 0.650
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.236
_diffrn_reflns_theta_min         5.303
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_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    -53.00  26.00   0.50    0.32    --  -46.62  37.00 -60.00  158
  2  ω     80.00 113.00   0.50    0.32    --   46.62 152.00  74.00   66
  3  ω    -66.00 -33.00   0.50    1.28    -- -106.00  57.00-150.00   66
  4  ω   -116.00 -55.00   0.50    1.28    -- -106.00 125.00 -68.00  122
  5  ω   -115.00 -68.00   0.50    1.28    -- -106.00 125.00-120.00   94
  6  ω   -113.00 -87.00   0.50    1.28    -- -106.00  57.00-150.00   52
  7  ω   -121.00 -32.00   0.50    1.28    -- -106.00  19.00 -30.00  178
  8  ω   -151.00 -69.00   0.50    1.28    -- -106.00-131.00-121.00  164
  9  ω   -177.00-116.00   0.50    1.28    -- -106.00 -99.00  30.00  122
;
_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      -0.0631062000
_diffrn_orient_matrix_UB_12      0.0419843000
_diffrn_orient_matrix_UB_13      -0.0255328000
_diffrn_orient_matrix_UB_21      -0.0852402000
_diffrn_orient_matrix_UB_22      -0.0979972000
_diffrn_orient_matrix_UB_23      -0.0061289000
_diffrn_orient_matrix_UB_31      -0.0110098000
_diffrn_orient_matrix_UB_32      0.0023887000
_diffrn_orient_matrix_UB_33      0.1959698000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.288
_reflns_Friedel_fraction_full    0.285
_reflns_Friedel_fraction_max     0.294
_reflns_number_gt                559
_reflns_number_total             563
_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 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 118 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.6(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     83
_refine_ls_number_reflns         563
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0366
_refine_ls_restrained_S_all      1.105
_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)+(0.0690P)²+0.6215P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.0973
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Sof(H3)=Sof(H2)=1-FVAR(1)
 Sof(F1)=Sof(F2)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C2(H2)
;
_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
C6 C -0.56941(15) -0.28022(15) -0.4267(3) 0.0293(6) Uani 1 1 d . . . . .
C3 C -0.49984(16) -0.10732(15) -0.5734(4) 0.0348(6) Uani 1 1 d . . . . .
H3 H -0.474058 -0.047734 -0.617720 0.042 Uiso 0.845(5) 1 calc R U P . .
C1 C -0.48361(15) -0.24226(16) -0.5075(4) 0.0311(6) Uani 1 1 d . . . . .
C5 C -0.62085(16) -0.23602(14) -0.4268(3) 0.0297(6) Uani 1 1 d . . . . .
C7 C -0.46532(16) -0.32327(16) -0.5430(4) 0.0337(6) Uani 1 1 d . . . A 1
H7A H -0.418279 -0.320816 -0.466408 0.040 Uiso 1 1 calc R U . A 1
H7B H -0.446060 -0.322261 -0.660888 0.040 Uiso 1 1 calc R U . A 1
C4 C -0.58968(16) -0.15059(15) -0.5075(4) 0.0316(6) Uani 1 1 d . . . . .
C2 C -0.44699(16) -0.15307(15) -0.5738(3) 0.0338(6) Uani 1 1 d . . . . .
H2 H -0.387365 -0.123066 -0.618777 0.041 Uiso 0.845(5) 1 calc R U P . .
F1 F -0.4346(5) -0.3233(5) -0.6935(11) 0.028(2) Uani 0.155(5) 1 d . . P B 2
F2 F -0.3936(5) -0.3141(6) -0.4247(12) 0.033(3) Uani 0.155(5) 1 d . . P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C6 C1 1.393(3) . ?
C6 C5 1.383(3) . ?
C6 C5 1.431(3) 3_445 ?
C3 H3 0.9300 . ?
C3 C4 1.396(3) . ?
C3 C2 1.426(3) . ?
C1 C7 1.552(3) . ?
C1 C2 1.394(3) . ?
C5 C4 1.398(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C4 1.553(3) 3_445 ?
C2 H2 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 C6 C5 111.0(2) . 3_445 ?
C5 C6 C1 121.9(2) . . ?
C5 C6 C5 120.0(2) . 3_445 ?
C4 C3 H3 119.5 . . ?
C4 C3 C2 121.0(2) . . ?
C2 C3 H3 119.5 . . ?
C6 C1 C7 106.8(2) . . ?
C6 C1 C2 117.0(2) . . ?
C2 C1 C7 133.7(3) . . ?
C6 C5 C6 120.0(2) . 2_455 ?
C6 C5 C4 122.0(2) . . ?
C4 C5 C6 111.0(2) . 2_455 ?
C1 C7 H7A 111.2 . . ?
C1 C7 H7B 111.2 . . ?
C1 C7 C4 103.03(17) . 3_445 ?
H7A C7 H7B 109.1 . . ?
C4 C7 H7A 111.2 3_445 . ?
C4 C7 H7B 111.2 3_445 . ?
C3 C4 C5 116.6(2) . . ?
C3 C4 C7 134.3(2) . 2_455 ?
C5 C4 C7 106.57(19) . 2_455 ?
C3 C2 H2 119.6 . . ?
C1 C2 C3 120.8(2) . . ?
C1 C2 H2 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C7 C4 12.0(3) . . . 3_445 ?
C6 C1 C2 C3 -6.2(4) . . . . ?
C6 C5 C4 C3 -6.3(4) . . . . ?
C6 C5 C4 C3 -156.9(2) 2_455 . . . ?
C6 C5 C4 C7 7.7(3) 2_455 . . 2_455 ?
C6 C5 C4 C7 158.4(2) . . . 2_455 ?
C1 C6 C5 C6 147.9(2) . . . 2_455 ?
C1 C6 C5 C4 -0.2(4) . . . . ?
C5 C6 C1 C7 -158.4(2) . . . . ?
C5 C6 C1 C7 -8.1(3) 3_445 . . . ?
C5 C6 C1 C2 156.8(2) 3_445 . . . ?
C5 C6 C1 C2 6.5(4) . . . . ?
C5 C6 C5 C6 0.1(4) 3_445 . . 2_455 ?
C5 C6 C5 C4 -148.0(2) 3_445 . . . ?
C7 C1 C2 C3 153.6(3) . . . . ?
C4 C3 C2 C1 -0.3(4) . . . . ?
C2 C3 C4 C5 6.4(4) . . . . ?
C2 C3 C4 C7 -152.8(3) . . . 2_455 ?
C2 C1 C7 C4 -149.2(3) . . . 3_445 ?

_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 1.733
_oxdiff_exptl_absorpt_empirical_full_min 0.525
####################################################################### 
# 
# 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_crystal-16
_database_code_depnum_ccdc_archive 'CCDC 2172519'
loop_
_audit_author_name
_audit_author_address
'Yumi Yakiyama'
;Osaka University
Japan
;
_audit_update_record             
;
2022-05-13 deposited with the CCDC.	2022-07-11 downloaded from the CCDC.
;
_audit_creation_date             2022-05-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H11.791, 0.209(F)'
_chemical_formula_sum            'C21 H11.79 F0.21'
_chemical_formula_weight         268.05
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      trigonal
_space_group_IT_number           161
_space_group_name_H-M_alt        'R 3 c'
_space_group_name_Hall           'R 3 -2"c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-y, -x, z+1/2'
'-x+y, y, z+1/2'
'x, x-y, z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'-y+2/3, -x+1/3, z+5/6'
'-x+y+2/3, y+1/3, z+5/6'
'x+2/3, x-y+1/3, z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-y+1/3, -x+2/3, z+7/6'
'-x+y+1/3, y+2/3, z+7/6'
'x+1/3, x-y+2/3, z+7/6'

_cell_length_a                   16.6293(5)
_cell_length_b                   16.6293(5)
_cell_length_c                   7.6551(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1833.28(12)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    2504
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      75.4620
_cell_measurement_theta_min      5.3140
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.654
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.20544
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             838
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2891
_diffrn_reflns_point_group_measured_fraction_full 0.749
_diffrn_reflns_point_group_measured_fraction_max 0.745
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.681
_diffrn_reflns_theta_min         5.320
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     80.00 107.00   0.50    1.83    --   70.50  84.00  -5.00   54
  2  ω    118.00 143.00   0.50    1.83    --   70.50  84.00  -5.00   50
  3  ω     72.00  98.00   0.50    0.46    --   46.62 125.00  30.00   52
  4  ω    -57.00 -31.00   0.50    1.83    -- -106.00  19.00   0.00   52
  5  ω    -80.00 -42.00   0.50    1.83    -- -106.00  57.00  60.00   76
  6  ω    -92.00 -47.00   0.50    1.83    -- -106.00  75.00 -26.00   90
  7  ω    -83.00 -35.00   0.50    1.83    -- -106.00 125.00  30.00   96
  8  ω   -111.00 -69.00   0.50    1.83    -- -106.00  19.00   0.00   84
  9  ω   -129.00-103.00   0.50    1.83    -- -106.00  75.00 -26.00   52
 10  ω   -117.00 -86.00   0.50    1.83    -- -106.00 125.00  30.00   62
 11  ω    -99.00 -43.00   0.50    1.83    -- -106.00 125.00-180.00  112
 12  ω   -175.00-142.00   0.50    1.83    -- -106.00 -73.00-178.00   66
 13  ω   -120.00 -94.00   0.50    1.83    -- -106.00 -73.00-178.00   52
 14  ω   -173.00 -83.00   0.50    1.83    -- -106.00 -75.00-154.00  180
 15  ω   -118.00 -90.00   0.50    0.46    --  -46.62-125.00   0.00   56
 16  ω   -123.00 -85.00   0.50    1.83    -- -106.00 -77.00 150.00   76
 17  ω     10.00  94.00   0.50    0.46    --   46.62-125.00  30.00  168
;
_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      -0.0350173000
_diffrn_orient_matrix_UB_12      -0.1036252000
_diffrn_orient_matrix_UB_13      0.0346309000
_diffrn_orient_matrix_UB_21      -0.0799922000
_diffrn_orient_matrix_UB_22      -0.0060753000
_diffrn_orient_matrix_UB_23      0.1116301000
_diffrn_orient_matrix_UB_31      -0.0618261000
_diffrn_orient_matrix_UB_32      -0.0259698000
_diffrn_orient_matrix_UB_33      -0.1636576000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.480
_reflns_Friedel_fraction_full    0.492
_reflns_Friedel_fraction_max     0.489
_reflns_number_gt                632
_reflns_number_total             635
_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 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Flack x determined using 204 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -2.0(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     73
_refine_ls_number_reflns         635
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0337
_refine_ls_restrained_S_all      1.101
_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)+(0.0573P)²+0.9429P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0897
_refine_ls_wR_factor_ref         0.0898
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Sof(H7A)=Sof(H7B)=1-FVAR(1)
 Sof(F1)=Sof(F2)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
3.b Aromatic/amide H refined with riding coordinates:
 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
C5 C -0.89405(14) -0.50113(15) -0.5731(4) 0.0250(5) Uani 1 1 d . . . . .
H5 H -0.954134 -0.527317 -0.616800 0.030 Uiso 1 1 calc R U . . .
C2 C -0.71984(14) -0.43086(14) -0.4267(3) 0.0211(5) Uani 1 1 d . . . . .
C3 C -0.76453(14) -0.37931(15) -0.4267(3) 0.0212(5) Uani 1 1 d . . . . .
C7 C -0.67648(15) -0.53557(14) -0.5451(3) 0.0246(5) Uani 1 1 d . . . A 1
H7A H -0.678782 -0.582993 -0.468044 0.030 Uiso 0.965(5) 1 calc R U P B 1
H7B H -0.677429 -0.554331 -0.665369 0.030 Uiso 0.965(5) 1 calc R U P B 1
C1 C -0.75802(15) -0.51740(14) -0.5076(4) 0.0223(5) Uani 1 1 d . . . . .
C4 C -0.85008(14) -0.41033(15) -0.5079(3) 0.0229(5) Uani 1 1 d . . . . .
C6 C -0.84785(15) -0.55429(15) -0.5735(3) 0.0248(5) Uani 1 1 d . . . . .
H6 H -0.878194 -0.614307 -0.618309 0.030 Uiso 1 1 calc R U . . .
F1 F -0.675(2) -0.565(2) -0.695(5) 0.020(10) Uiso 0.035(5) 1 d . . P B 2
F2 F -0.689(2) -0.611(2) -0.423(5) 0.020(10) Uiso 0.035(5) 1 d . . P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C5 H5 0.9300 . ?
C5 C4 1.400(3) . ?
C5 C6 1.432(3) . ?
C2 C3 1.429(3) 2_455 ?
C2 C3 1.387(3) . ?
C2 C1 1.394(3) . ?
C3 C4 1.394(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C1 1.556(3) . ?
C7 C4 1.550(3) 2_455 ?
C1 C6 1.395(3) . ?
C6 H6 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 C5 H5 119.5 . . ?
C4 C5 C6 120.97(19) . . ?
C6 C5 H5 119.5 . . ?
C3 C2 C3 120.3(2) . 2_455 ?
C3 C2 C1 122.0(2) . . ?
C1 C2 C3 110.9(2) . 2_455 ?
C2 C3 C2 119.7(2) . 3_445 ?
C2 C3 C4 122.3(2) . . ?
C4 C3 C2 111.0(2) . 3_445 ?
H7A C7 H7B 109.1 . . ?
C1 C7 H7A 111.2 . . ?
C1 C7 H7B 111.2 . . ?
C4 C7 H7A 111.2 2_455 . ?
C4 C7 H7B 111.2 2_455 . ?
C4 C7 C1 102.75(16) 2_455 . ?
C2 C1 C7 106.92(19) . . ?
C2 C1 C6 116.7(2) . . ?
C6 C1 C7 133.9(2) . . ?
C5 C4 C7 134.2(2) . 3_445 ?
C3 C4 C5 116.37(19) . . ?
C3 C4 C7 107.05(18) . 3_445 ?
C5 C6 H6 119.5 . . ?
C1 C6 C5 121.0(2) . . ?
C1 C6 H6 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C3 C4 C5 7.0(3) . . . . ?
C2 C3 C4 C5 157.6(2) 3_445 . . . ?
C2 C3 C4 C7 -158.1(2) . . . 3_445 ?
C2 C3 C4 C7 -7.5(3) 3_445 . . 3_445 ?
C2 C1 C6 C5 6.1(4) . . . . ?
C3 C2 C3 C2 0.1(4) 2_455 . . 3_445 ?
C3 C2 C3 C4 148.16(19) 2_455 . . . ?
C3 C2 C1 C7 7.2(3) 2_455 . . . ?
C3 C2 C1 C7 158.3(2) . . . . ?
C3 C2 C1 C6 -6.3(4) . . . . ?
C3 C2 C1 C6 -157.4(2) 2_455 . . . ?
C7 C1 C6 C5 -153.3(2) . . . . ?
C1 C2 C3 C2 -148.41(19) . . . 3_445 ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C4 C5 C6 C1 0.5(4) . . . . ?
C4 C7 C1 C2 -11.0(3) 2_455 . . . ?
C4 C7 C1 C6 149.8(2) 2_455 . . . ?
C6 C5 C4 C3 -7.0(3) . . . . ?
C6 C5 C4 C7 152.9(2) . . . 3_445 ?

_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 2.765
_oxdiff_exptl_absorpt_empirical_full_min 0.267
####################################################################### 
# 
# 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_crystal-5
_database_code_depnum_ccdc_archive 'CCDC 2172518'
loop_
_audit_author_name
_audit_author_address
'Yumi Yakiyama'
;Osaka University
Japan
;
_audit_update_record             
;
2022-05-13 deposited with the CCDC.	2022-07-11 downloaded from the CCDC.
;
_audit_creation_date             2022-05-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H11.193, 0.807(F)'
_chemical_formula_sum            'C21 H11.19 F0.81'
_chemical_formula_weight         278.82
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      trigonal
_space_group_IT_number           161
_space_group_name_H-M_alt        'R 3 c'
_space_group_name_Hall           'R 3 -2"c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-y, -x, z+1/2'
'-x+y, y, z+1/2'
'x, x-y, z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'-y+2/3, -x+1/3, z+5/6'
'-x+y+2/3, y+1/3, z+5/6'
'x+2/3, x-y+1/3, z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-y+1/3, -x+2/3, z+7/6'
'-x+y+1/3, y+2/3, z+7/6'
'x+1/3, x-y+2/3, z+7/6'

_cell_length_a                   16.6500(6)
_cell_length_b                   16.6500(6)
_cell_length_c                   7.7389(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1857.97(15)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    5560
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      30.6810
_cell_measurement_theta_min      4.1950
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81402
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             867
_exptl_crystal_size_max          0.174
_exptl_crystal_size_mid          0.148
_exptl_crystal_size_min          0.087
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_unetI/netI     0.0148
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.914
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6537
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.833
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.744
_diffrn_reflns_theta_min         2.446
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.914
_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  59.00   0.50   17.57    --    5.49  75.00 -29.00   54
  2  ω     -5.00  25.00   0.50   17.57    --    5.49  75.00 -29.00   60
  3  ω     -8.00  79.00   0.50   17.57    --    5.49  38.00  90.00  174
  4  ω      1.00  29.00   0.50   17.57    --    5.49 -99.00  30.00   56
  5  ω    -61.00  -9.00   0.50   17.57    --   -5.42 -38.00 -90.00  104
  6  ω     -8.00  75.00   0.50   17.57    --    5.49  48.00-176.00  166
;
_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      -0.0481390000
_diffrn_orient_matrix_UB_12      -0.0218051000
_diffrn_orient_matrix_UB_13      -0.0184921000
_diffrn_orient_matrix_UB_21      -0.0034754000
_diffrn_orient_matrix_UB_22      0.0334197000
_diffrn_orient_matrix_UB_23      0.0513829000
_diffrn_orient_matrix_UB_31      0.0095848000
_diffrn_orient_matrix_UB_32      0.0287451000
_diffrn_orient_matrix_UB_33      -0.0735624000
_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         0.808
_reflns_Friedel_fraction_full    0.975
_reflns_Friedel_fraction_max     0.751
_reflns_number_gt                1073
_reflns_number_total             1081
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 474 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     83
_refine_ls_number_reflns         1081
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0333
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0688P)²+0.4337P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.0935
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Sof(H7A)=Sof(H7B)=1-FVAR(1)
 Sof(F1)=Sof(F2)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
C1 C 0.51664(11) 0.75774(11) 0.4926(3) 0.0233(4) Uani 1 1 d . . . . .
C2 C 0.55332(12) 0.84733(11) 0.4265(2) 0.0262(4) Uani 1 1 d . . . . .
H2 H 0.613154 0.877524 0.381646 0.031 Uiso 1 1 calc R U . . .
C3 C 0.50044(11) 0.89327(11) 0.4268(3) 0.0260(4) Uani 1 1 d . . . . .
H3 H 0.526351 0.953050 0.382532 0.031 Uiso 1 1 calc R U . . .
C4 C 0.41016(12) 0.84968(11) 0.4928(2) 0.0235(4) Uani 1 1 d . . . . .
C5 C 0.37937(11) 0.76424(11) 0.5735(2) 0.0215(4) Uani 1 1 d . . . . .
C6 C 0.43062(11) 0.71976(11) 0.5739(2) 0.0215(4) Uani 1 1 d . . . . .
C7 C 0.53512(12) 0.67678(12) 0.4568(2) 0.0260(4) Uani 1 1 d . . . A 1
H7A H 0.554278 0.677732 0.338042 0.031 Uiso 0.866(4) 1 calc R U P B 1
H7B H 0.582338 0.679303 0.533652 0.031 Uiso 0.866(4) 1 calc R U P B 1
F1 F 0.6064(5) 0.6858(5) 0.5762(11) 0.030(2) Uani 0.134(4) 1 d . . P B 2
F2 F 0.5650(5) 0.6769(5) 0.3072(10) 0.027(2) Uani 0.134(4) 1 d . . P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.396(2) . ?
C1 C6 1.393(2) . ?
C1 C7 1.550(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.426(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.399(2) . ?
C4 C5 1.395(2) . ?
C4 C7 1.550(2) 2_665 ?
C5 C6 1.431(2) 2_665 ?
C5 C6 1.381(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C7 133.85(18) . . ?
C6 C1 C2 116.84(15) . . ?
C6 C1 C7 106.98(14) . . ?
C1 C2 H2 119.5 . . ?
C1 C2 C3 121.00(16) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 120.92(15) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C7 134.21(16) . 2_665 ?
C5 C4 C3 116.37(15) . . ?
C5 C4 C7 106.93(14) . 2_665 ?
C4 C5 C6 110.84(15) . 2_665 ?
C6 C5 C4 122.47(15) . . ?
C6 C5 C6 119.80(17) . 2_665 ?
C1 C6 C5 110.87(15) . 3_565 ?
C5 C6 C1 121.74(15) . . ?
C5 C6 C5 120.20(17) . 3_565 ?
C1 C7 H7A 111.2 . . ?
C1 C7 H7B 111.2 . . ?
C4 C7 C1 102.84(13) 3_565 . ?
C4 C7 H7A 111.2 3_565 . ?
C4 C7 H7B 111.2 3_565 . ?
H7A C7 H7B 109.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -0.2(3) . . . . ?
C2 C1 C6 C5 156.98(16) . . . 3_565 ?
C2 C1 C6 C5 6.7(3) . . . . ?
C2 C1 C7 C4 -149.58(19) . . . 3_565 ?
C2 C3 C4 C5 6.5(3) . . . . ?
C2 C3 C4 C7 -152.81(18) . . . 2_665 ?
C3 C4 C5 C6 -157.17(16) . . . 2_665 ?
C3 C4 C5 C6 -6.4(2) . . . . ?
C4 C5 C6 C1 -0.2(3) . . . . ?
C4 C5 C6 C5 -147.86(14) . . . 3_565 ?
C6 C1 C2 C3 -6.4(3) . . . . ?
C6 C1 C7 C4 11.9(2) . . . 3_565 ?
C6 C5 C6 C1 148.04(14) 2_665 . . . ?
C6 C5 C6 C5 0.4(3) 2_665 . . 3_565 ?
C7 C1 C2 C3 153.69(19) . . . . ?
C7 C1 C6 C5 -158.44(15) . . . . ?
C7 C1 C6 C5 -8.1(2) . . . 3_565 ?
C7 C4 C5 C6 158.27(15) 2_665 . . . ?
C7 C4 C5 C6 7.50(19) 2_665 . . 2_665 ?

_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 1.330
_oxdiff_exptl_absorpt_empirical_full_min 0.848
####################################################################### 
# 
# 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_crystal-10
_database_code_depnum_ccdc_archive 'CCDC 2172512'
loop_
_audit_author_name
_audit_author_address
'Yumi Yakiyama'
;Osaka University
Japan
;
_audit_update_record             
;
2022-05-13 deposited with the CCDC.	2022-07-11 downloaded from the CCDC.
;
_audit_creation_date             2022-05-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H10.791, 1.209(F)'
_chemical_formula_sum            'C21 H10.79 F1.21'
_chemical_formula_weight         286.05
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      trigonal
_space_group_IT_number           161
_space_group_name_H-M_alt        'R 3 c'
_space_group_name_Hall           'R 3 -2"c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-y, -x, z+1/2'
'-x+y, y, z+1/2'
'x, x-y, z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'-y+2/3, -x+1/3, z+5/6'
'-x+y+2/3, y+1/3, z+5/6'
'x+2/3, x-y+1/3, z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-y+1/3, -x+2/3, z+7/6'
'-x+y+1/3, y+2/3, z+7/6'
'x+1/3, x-y+2/3, z+7/6'

_cell_length_a                   16.7228(10)
_cell_length_b                   16.7228(10)
_cell_length_c                   7.8675(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1905.4(3)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    1683
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      75.3330
_cell_measurement_theta_min      5.2640
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.695
_exptl_absorpt_coefficient_mu    0.786
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31562
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             886
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0871
_diffrn_reflns_av_unetI/netI     0.0488
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2215
_diffrn_reflns_point_group_measured_fraction_full 0.854
_diffrn_reflns_point_group_measured_fraction_max 0.840
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.814
_diffrn_reflns_theta_min         5.290
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     84.00 129.00   0.50    2.11    --   70.50 102.00 -66.00   90
  2  ω     76.00 114.00   0.50    0.53    --   46.62 125.00  30.00   76
  3  ω     76.00 124.00   0.50    2.11    --   70.50 127.00  63.00   96
  4  ω    -77.00 -51.00   0.50    2.11    -- -106.00 125.00 -30.00   52
  5  ω   -116.00 -45.00   0.50    2.11    -- -106.00 158.00  61.00  142
  6  ω   -116.00 -82.00   0.50    2.11    -- -106.00 125.00 -30.00   68
  7  ω   -101.00 -74.00   0.50    2.11    -- -106.00 125.00-150.00   54
  8  ω   -171.00-144.00   0.50    2.11    -- -106.00 -37.00 -60.00   54
  9  ω   -136.00 -90.00   0.50    2.11    -- -106.00 -57.00 -90.00   92
 10  ω   -129.00 -92.00   0.50    2.11    -- -106.00 -37.00 -60.00   74
 11  ω   -101.00 -71.00   0.50    0.53    --  -46.62-125.00 -90.00   60
 12  ω   -170.00-103.00   0.50    2.11    -- -106.00 -57.00-180.00  134
 13  ω   -174.00-143.00   0.50    2.11    -- -106.00 -57.00 -90.00   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      0.0471855000
_diffrn_orient_matrix_UB_12      0.1025035000
_diffrn_orient_matrix_UB_13      -0.0520095000
_diffrn_orient_matrix_UB_21      0.0904897000
_diffrn_orient_matrix_UB_22      0.0169120000
_diffrn_orient_matrix_UB_23      0.0834900000
_diffrn_orient_matrix_UB_31      0.0300672000
_diffrn_orient_matrix_UB_32      -0.0231595000
_diffrn_orient_matrix_UB_33      -0.1692609000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.669
_reflns_Friedel_fraction_full    0.705
_reflns_Friedel_fraction_max     0.681
_reflns_number_gt                705
_reflns_number_total             746
_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 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details 
;
 Flack x determined using 259 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   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     83
_refine_ls_number_reflns         746
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0627
_refine_ls_restrained_S_all      1.078
_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)+(0.1250P)²+0.7249P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1685
_refine_ls_wR_factor_ref         0.1732
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Sof(H7A)=Sof(H7B)=1-FVAR(1)
 Sof(F1)=Sof(F2)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7578(3) 0.5157(3) 0.5076(7) 0.0408(10) Uani 1 1 d . . . . .
C2 C 0.8467(3) 0.5519(3) 0.5728(6) 0.0424(10) Uani 1 1 d . . . . .
H2 H 0.877742 0.612931 0.617213 0.051 Uiso 1 1 calc R U . . .
C3 C 0.8915(3) 0.4990(3) 0.5739(6) 0.0428(11) Uani 1 1 d . . . . .
H3 H 0.951764 0.524877 0.620693 0.051 Uiso 1 1 calc R U . . .
C4 C 0.8487(3) 0.4095(3) 0.5073(6) 0.0410(10) Uani 1 1 d . . . . .
C5 C 0.7638(2) 0.3788(3) 0.4268(6) 0.0370(10) Uani 1 1 d . . . . .
C6 C 0.7196(3) 0.4299(3) 0.4276(6) 0.0398(10) Uani 1 1 d . . . . .
C7 C 0.6775(3) 0.5346(3) 0.5430(6) 0.0450(11) Uani 1 1 d . . . A 1
H7A H 0.680299 0.582708 0.465887 0.054 Uiso 0.798(10) 1 calc R U P B 1
H7B H 0.678613 0.554061 0.662228 0.054 Uiso 0.798(10) 1 calc R U P B 1
F1 F 0.6852(7) 0.6046(7) 0.4253(17) 0.041(4) Uani 0.202(10) 1 d . . P B 2
F2 F 0.6769(7) 0.5659(7) 0.6900(14) 0.035(3) Uani 0.202(10) 1 d . . P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.394(6) . ?
C1 C6 1.396(6) . ?
C1 C7 1.550(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.416(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.399(6) . ?
C4 C5 1.398(5) . ?
C4 C7 1.556(6) 3_665 ?
C5 C6 1.428(5) 3_665 ?
C5 C6 1.380(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 116.9(4) . . ?
C2 C1 C7 133.6(5) . . ?
C6 C1 C7 107.1(4) . . ?
C1 C2 H2 119.5 . . ?
C1 C2 C3 120.9(4) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.3(4) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C7 134.2(4) . 3_665 ?
C5 C4 C3 116.4(3) . . ?
C5 C4 C7 106.8(3) . 3_665 ?
C4 C5 C6 111.0(4) . 3_665 ?
C6 C5 C4 122.1(4) . . ?
C6 C5 C6 119.5(4) . 3_665 ?
C1 C6 C5 110.9(4) . 2_655 ?
C5 C6 C1 121.8(4) . . ?
C5 C6 C5 120.5(4) . 2_655 ?
C1 C7 C4 102.7(3) . 2_655 ?
C1 C7 H7A 111.2 . . ?
C1 C7 H7B 111.2 . . ?
C4 C7 H7A 111.2 2_655 . ?
C4 C7 H7B 111.2 2_655 . ?
H7A C7 H7B 109.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 1.0(7) . . . . ?
C2 C1 C6 C5 157.3(4) . . . 2_655 ?
C2 C1 C6 C5 6.0(7) . . . . ?
C2 C1 C7 C4 -149.5(5) . . . 2_655 ?
C2 C3 C4 C5 5.6(6) . . . . ?
C2 C3 C4 C7 -153.0(4) . . . 3_665 ?
C3 C4 C5 C6 -156.0(4) . . . 3_665 ?
C3 C4 C5 C6 -6.4(6) . . . . ?
C4 C5 C6 C1 0.6(7) . . . . ?
C4 C5 C6 C5 -147.9(4) . . . 2_655 ?
C6 C1 C2 C3 -6.8(7) . . . . ?
C6 C1 C7 C4 11.8(6) . . . 2_655 ?
C6 C5 C6 C1 147.7(4) 3_665 . . . ?
C6 C5 C6 C5 -0.9(8) 3_665 . . 2_655 ?
C7 C1 C2 C3 153.1(5) . . . . ?
C7 C1 C6 C5 -158.9(4) . . . . ?
C7 C1 C6 C5 -7.6(6) . . . 2_655 ?
C7 C4 C5 C6 157.7(4) 3_665 . . . ?
C7 C4 C5 C6 8.2(5) 3_665 . . 3_665 ?

_olex2_exptl_crystal_mounting_method Litholoop
_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 2.331
_oxdiff_exptl_absorpt_empirical_full_min 0.454
####################################################################### 
# 
# 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_crystal-11
_database_code_depnum_ccdc_archive 'CCDC 2172510'
loop_
_audit_author_name
_audit_author_address
'Yumi Yakiyama'
;Osaka University
Japan
;
_audit_update_record             
;
2022-05-13 deposited with the CCDC.	2022-07-11 downloaded from the CCDC.
;
_audit_creation_date             2022-05-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H10.475, 1.525(F)'
_chemical_formula_sum            'C21 H10.47 F1.53'
_chemical_formula_weight         291.74
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      trigonal
_space_group_IT_number           161
_space_group_name_H-M_alt        'R 3 c'
_space_group_name_Hall           'R 3 -2"c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-y, -x, z+1/2'
'-x+y, y, z+1/2'
'x, x-y, z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'-y+2/3, -x+1/3, z+5/6'
'-x+y+2/3, y+1/3, z+5/6'
'x+2/3, x-y+1/3, z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-y+1/3, -x+2/3, z+7/6'
'-x+y+1/3, y+2/3, z+7/6'
'x+1/3, x-y+2/3, z+7/6'

_cell_length_a                   16.7403(17)
_cell_length_b                   16.7403(17)
_cell_length_c                   7.9040(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1918.2(4)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    1177
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      73.5060
_cell_measurement_theta_min      5.2720
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.830
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46421
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             901
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0751
_diffrn_reflns_av_unetI/netI     0.0443
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2106
_diffrn_reflns_point_group_measured_fraction_full 0.935
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.377
_diffrn_reflns_theta_min         5.285
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'CCD plate'
_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     82.00 141.00   0.50    3.26    --   70.50 106.00 128.00  118
  2  ω    -76.00 -31.00   0.50    3.26    -- -106.00  19.00-180.00   90
  3  ω   -110.00 -81.00   0.50    3.26    -- -106.00  19.00-180.00   58
  4  ω   -121.00 -62.00   0.50    3.26    -- -106.00  37.00-150.00  118
  5  ω   -131.00 -53.00   0.50    3.26    -- -106.00  82.00  40.00  156
  6  ω   -156.00 -87.00   0.50    3.26    -- -106.00 -77.00-180.00  138
  7  ω   -119.00 -73.00   0.50    0.82    --  -46.62-125.00 -60.00   92
  8  ω   -144.00 -85.00   0.50    3.26    -- -106.00 -77.00  90.00  118
  9  ω   -118.00 -71.00   0.50    0.82    --  -46.62-125.00 150.00   94
 10  ω   -171.00-141.00   0.50    3.26    -- -106.00-112.00 -60.00   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      0.0278080000
_diffrn_orient_matrix_UB_12      -0.0730732000
_diffrn_orient_matrix_UB_13      0.0382349000
_diffrn_orient_matrix_UB_21      -0.0319549000
_diffrn_orient_matrix_UB_22      -0.0054915000
_diffrn_orient_matrix_UB_23      0.1846296000
_diffrn_orient_matrix_UB_31      -0.0974156000
_diffrn_orient_matrix_UB_32      -0.0769699000
_diffrn_orient_matrix_UB_33      -0.0494388000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.806
_reflns_Friedel_fraction_full    0.867
_reflns_Friedel_fraction_max     0.825
_reflns_number_gt                754
_reflns_number_total             811
_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 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.415
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.105
_refine_ls_abs_structure_details 
;
 Flack x determined using 297 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.8(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     83
_refine_ls_number_reflns         811
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_gt           0.0772
_refine_ls_restrained_S_all      1.095
_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)+(0.1616P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1976
_refine_ls_wR_factor_ref         0.2035
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Sof(H7A)=Sof(H7B)=1-FVAR(1)
 Sof(F1)=Sof(F2)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
3.b Aromatic/amide H refined with riding coordinates:
 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
C1 C 0.2420(3) 0.4846(3) 0.4934(8) 0.0439(11) Uani 1 1 d . . . . .
C2 C 0.2901(3) 0.5704(3) 0.5730(6) 0.0422(11) Uani 1 1 d . . . . .
C3 C 0.3846(3) 0.6212(3) 0.5721(6) 0.0437(12) Uani 1 1 d . . . . .
C4 C 0.4391(3) 0.5903(3) 0.4932(7) 0.0453(12) Uani 1 1 d . . . . .
C5 C 0.3925(3) 0.5014(3) 0.4259(7) 0.0487(12) Uani 1 1 d . . . . .
H5 H 0.426130 0.476300 0.379614 0.058 Uiso 1 1 calc R U . . .
C6 C 0.2944(3) 0.4483(3) 0.4267(6) 0.0456(12) Uani 1 1 d . . . . .
H6 H 0.264930 0.388921 0.382348 0.055 Uiso 1 1 calc R U . . .
C7 C 0.1432(3) 0.4660(3) 0.4585(7) 0.0497(12) Uani 1 1 d . . . A 1
H7A H 0.098888 0.418973 0.533903 0.060 Uiso 0.746(12) 1 calc R U P B 1
H7B H 0.125078 0.446689 0.342305 0.060 Uiso 0.746(12) 1 calc R U P B 1
F1 F 0.0817(7) 0.3965(7) 0.5728(14) 0.050(3) Uani 0.254(12) 1 d . . P B 2
F2 F 0.1136(8) 0.4358(7) 0.3094(13) 0.046(3) Uani 0.254(12) 1 d . . P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.396(7) . ?
C1 C6 1.396(6) . ?
C1 C7 1.547(6) . ?
C2 C3 1.372(6) . ?
C2 C3 1.430(6) 3_565 ?
C3 C4 1.400(6) . ?
C4 C5 1.394(7) . ?
C4 C7 1.551(7) 2_665 ?
C5 H5 0.9300 . ?
C5 C6 1.424(6) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 117.0(4) . . ?
C2 C1 C7 107.3(4) . . ?
C6 C1 C7 133.3(5) . . ?
C1 C2 C3 110.4(4) . 3_565 ?
C3 C2 C1 121.9(4) . . ?
C3 C2 C3 120.3(5) . 3_565 ?
C2 C3 C2 119.6(5) . 2_665 ?
C2 C3 C4 122.4(4) . . ?
C4 C3 C2 111.3(4) . 2_665 ?
C3 C4 C7 106.4(4) . 2_665 ?
C5 C4 C3 116.3(4) . . ?
C5 C4 C7 134.3(5) . 2_665 ?
C4 C5 H5 119.3 . . ?
C4 C5 C6 121.3(4) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C5 120.6(4) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C1 C7 C4 103.0(3) . 3_565 ?
C1 C7 H7A 111.2 . . ?
C1 C7 H7B 111.2 . . ?
C4 C7 H7A 111.2 3_565 . ?
C4 C7 H7B 111.2 3_565 . ?
H7A C7 H7B 109.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C2 148.2(4) . . . 2_665 ?
C1 C2 C3 C4 -0.7(7) . . . . ?
C2 C1 C6 C5 -6.2(8) . . . . ?
C2 C1 C7 C4 11.9(6) . . . 3_565 ?
C2 C3 C4 C5 -155.9(4) 2_665 . . . ?
C2 C3 C4 C5 -4.7(7) . . . . ?
C2 C3 C4 C7 158.6(4) . . . 2_665 ?
C2 C3 C4 C7 7.4(6) 2_665 . . 2_665 ?
C3 C2 C3 C2 1.0(9) 3_565 . . 2_665 ?
C3 C2 C3 C4 -147.9(4) 3_565 . . . ?
C3 C4 C5 C6 4.6(7) . . . . ?
C4 C5 C6 C1 0.8(8) . . . . ?
C6 C1 C2 C3 156.2(5) . . . 3_565 ?
C6 C1 C2 C3 6.2(8) . . . . ?
C6 C1 C7 C4 -148.9(6) . . . 3_565 ?
C7 C1 C2 C3 -8.2(6) . . . 3_565 ?
C7 C1 C2 C3 -158.2(4) . . . . ?
C7 C1 C6 C5 153.2(5) . . . . ?
C7 C4 C5 C6 -152.8(5) 2_665 . . . ?

_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 2.381
_oxdiff_exptl_absorpt_empirical_full_min 0.444
####################################################################### 
# 
# 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_crystal-12
_database_code_depnum_ccdc_archive 'CCDC 2172511'
loop_
_audit_author_name
_audit_author_address
'Yumi Yakiyama'
;Osaka University
Japan
;
_audit_update_record             
;
2022-05-13 deposited with the CCDC.	2022-07-11 downloaded from the CCDC.
;
_audit_creation_date             2022-05-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H11.243, 0.758(F)'
_chemical_formula_sum            'C21 H11.24 F0.76'
_chemical_formula_weight         277.95
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      trigonal
_space_group_IT_number           161
_space_group_name_H-M_alt        'R 3 c'
_space_group_name_Hall           'R 3 -2"c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-y, -x, z+1/2'
'-x+y, y, z+1/2'
'x, x-y, z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'-y+2/3, -x+1/3, z+5/6'
'-x+y+2/3, y+1/3, z+5/6'
'x+2/3, x-y+1/3, z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-y+1/3, -x+2/3, z+7/6'
'-x+y+1/3, y+2/3, z+7/6'
'x+1/3, x-y+2/3, z+7/6'

_cell_length_a                   16.6665(3)
_cell_length_b                   16.6665(3)
_cell_length_c                   7.7333(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1860.30(8)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    2036
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      75.8830
_cell_measurement_theta_min      5.3010
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.733
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57357
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.086
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0157
_diffrn_reflns_av_unetI/netI     0.0133
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2150
_diffrn_reflns_point_group_measured_fraction_full 0.721
_diffrn_reflns_point_group_measured_fraction_max 0.702
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.051
_diffrn_reflns_theta_min         5.308
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -73.00 -47.00   0.50    0.41    -- -106.00 118.00-103.00   52
  2  ω    -81.00 -36.00   0.50    0.41    -- -106.00 125.00-180.00   90
  3  ω    -89.00 -33.00   0.50    0.41    -- -106.00 162.00 -94.00  112
  4  ω   -105.00 -66.00   0.50    0.41    -- -106.00  92.00-150.00   78
  5  ω   -141.00-102.00   0.50    0.41    -- -106.00 162.00 -94.00   78
  6  ω   -121.00 -84.00   0.50    0.41    -- -106.00  37.00 120.00   74
  7  ω    -74.00 -43.00   0.50    0.41    -- -106.00  37.00 120.00   62
  8  ω    -75.00 -48.00   0.50    0.41    -- -106.00 105.00 139.00   54
  9  ω   -118.00 -62.00   0.50    0.10    --  -46.62 -31.00-118.00  112
 10  ω     86.00 120.00   0.50    0.10    --   46.62 125.00-150.00   68
 11  ω    117.00 142.00   0.50    0.41    --   70.50 125.00 -30.00   50
 12  ω   -176.00 -90.00   0.50    0.41    -- -106.00 -99.00  60.00  172
;
_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      0.0001754000
_diffrn_orient_matrix_UB_12      0.0879064000
_diffrn_orient_matrix_UB_13      0.0625300000
_diffrn_orient_matrix_UB_21      0.1029852000
_diffrn_orient_matrix_UB_22      0.0589174000
_diffrn_orient_matrix_UB_23      -0.0497003000
_diffrn_orient_matrix_UB_31      -0.0279090000
_diffrn_orient_matrix_UB_32      0.0140757000
_diffrn_orient_matrix_UB_33      -0.1824560000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.394
_reflns_Friedel_fraction_full    0.434
_reflns_Friedel_fraction_max     0.401
_reflns_number_gt                604
_reflns_number_total             609
_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 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details 
;
 Flack x determined using 169 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     83
_refine_ls_number_reflns         609
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0366
_refine_ls_restrained_S_all      1.150
_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)+(0.0585P)²+1.4420P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0901
_refine_ls_wR_factor_ref         0.0981
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Sof(H7A)=Sof(H7B)=1-FVAR(1)
 Sof(F1)=Sof(F2)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C -0.49968(17) -0.39270(18) -0.5713(4) 0.0282(6) Uani 1 1 d . . . . .
H2 H -0.474000 -0.426540 -0.616511 0.034 Uiso 1 1 calc R U . . .
C5 C -0.56943(16) -0.28897(17) -0.4241(4) 0.0241(6) Uani 1 1 d . . . . .
C4 C -0.48360(17) -0.24121(18) -0.5047(4) 0.0258(6) Uani 1 1 d . . . . .
C6 C -0.62077(18) -0.38484(17) -0.4240(4) 0.0239(6) Uani 1 1 d . . . . .
C3 C -0.44658(18) -0.29377(19) -0.5710(4) 0.0291(6) Uani 1 1 d . . . . .
H3 H -0.386704 -0.264053 -0.615406 0.035 Uiso 1 1 calc R U . . .
C7 C -0.67665(18) -0.53505(18) -0.5414(4) 0.0284(7) Uani 1 1 d . . . A 1
H7A H -0.677665 -0.553934 -0.660411 0.034 Uiso 0.874(6) 1 calc R U P B 1
H7B H -0.679190 -0.582393 -0.464928 0.034 Uiso 0.874(6) 1 calc R U P B 1
C1 C -0.58946(18) -0.43922(16) -0.5047(4) 0.0266(6) Uani 1 1 d . . . . .
F1 F -0.6767(9) -0.5643(8) -0.6907(18) 0.034(4) Uani 0.126(6) 1 d . . P B 2
F2 F -0.6860(9) -0.6075(8) -0.417(2) 0.036(4) Uani 0.126(6) 1 d . . P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C2 H2 0.9300 . ?
C2 C3 1.429(4) . ?
C2 C1 1.395(4) . ?
C5 C4 1.389(3) . ?
C5 C6 1.427(3) 2_455 ?
C5 C6 1.385(3) . ?
C4 C3 1.397(4) . ?
C4 C7 1.555(3) 2_455 ?
C6 C1 1.398(4) . ?
C3 H3 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C1 1.556(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
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C1 C2 C3 120.9(2) . . ?
C4 C5 C6 111.2(2) . 2_455 ?
C6 C5 C4 121.8(2) . . ?
C6 C5 C6 120.1(2) . 2_455 ?
C5 C4 C3 117.2(2) . . ?
C5 C4 C7 107.0(2) . 2_455 ?
C3 C4 C7 133.4(3) . 2_455 ?
C5 C6 C5 119.9(2) . 3_445 ?
C5 C6 C1 122.1(2) . . ?
C1 C6 C5 111.0(2) . 3_445 ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.7(2) . . ?
C4 C3 H3 119.6 . . ?
C4 C7 H7A 111.2 3_445 . ?
C4 C7 H7B 111.2 3_445 . ?
C4 C7 C1 102.70(19) 3_445 . ?
H7A C7 H7B 109.1 . . ?
C1 C7 H7A 111.2 . . ?
C1 C7 H7B 111.2 . . ?
C2 C1 C6 116.7(2) . . ?
C2 C1 C7 134.0(3) . . ?
C6 C1 C7 106.7(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 C4 C3 C2 6.4(4) . . . . ?
C5 C6 C1 C2 156.7(3) 3_445 . . . ?
C5 C6 C1 C2 6.1(4) . . . . ?
C5 C6 C1 C7 -158.1(3) . . . . ?
C5 C6 C1 C7 -7.4(3) 3_445 . . . ?
C4 C5 C6 C5 -148.1(2) . . . 3_445 ?
C4 C5 C6 C1 0.0(4) . . . . ?
C4 C7 C1 C2 -148.9(3) 3_445 . . . ?
C4 C7 C1 C6 11.3(3) 3_445 . . . ?
C6 C5 C4 C3 -6.3(5) . . . . ?
C6 C5 C4 C3 -157.1(3) 2_455 . . . ?
C6 C5 C4 C7 7.7(3) 2_455 . . 2_455 ?
C6 C5 C4 C7 158.5(2) . . . 2_455 ?
C6 C5 C6 C5 0.1(5) 2_455 . . 3_445 ?
C6 C5 C6 C1 148.2(2) 2_455 . . . ?
C3 C2 C1 C6 -5.8(4) . . . . ?
C3 C2 C1 C7 152.8(3) . . . . ?
C7 C4 C3 C2 -153.4(3) 2_455 . . . ?
C1 C2 C3 C4 -0.4(4) . . . . ?

_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 1.228
_oxdiff_exptl_absorpt_empirical_full_min 0.622
####################################################################### 
# 
# 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_crystal-17
_database_code_depnum_ccdc_archive 'CCDC 2172520'
loop_
_audit_author_name
_audit_author_address
'Yumi Yakiyama'
;Osaka University
Japan
;
_audit_update_record             
;
2022-05-13 deposited with the CCDC.	2022-07-11 downloaded from the CCDC.
;
_audit_creation_date             2022-05-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '1(C21 H11.784), 0.216(F)'
_chemical_formula_sum            'C21 H11.79 F0.22'
_chemical_formula_weight         268.18
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      trigonal
_space_group_IT_number           161
_space_group_name_H-M_alt        'R 3 c'
_space_group_name_Hall           'R 3 -2"c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-y, -x, z+1/2'
'-x+y, y, z+1/2'
'x, x-y, z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'-y+2/3, -x+1/3, z+5/6'
'-x+y+2/3, y+1/3, z+5/6'
'x+2/3, x-y+1/3, z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-y+1/3, -x+2/3, z+7/6'
'-x+y+1/3, y+2/3, z+7/6'
'x+1/3, x-y+2/3, z+7/6'

_cell_length_a                   16.6267(4)
_cell_length_b                   16.6267(4)
_cell_length_c                   7.6522(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1832.01(10)
_cell_formula_units_Z            5.99994
_cell_measurement_reflns_used    2190
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      75.0100
_cell_measurement_theta_min      5.3190
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.656
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48575
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             838
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.087
_exptl_crystal_size_min          0.085
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2338
_diffrn_reflns_point_group_measured_fraction_full 0.772
_diffrn_reflns_point_group_measured_fraction_max 0.757
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.725
_diffrn_reflns_theta_min         5.321
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     31.00  69.00   0.50    0.09    --   46.62 -91.00-132.00   76
  2  ω    -88.00 -62.00   0.50    0.36    -- -106.00  94.00 -64.00   52
  3  ω    -69.00 -44.00   0.50    0.36    -- -106.00  57.00   0.00   50
  4  ω   -117.00 -67.00   0.50    0.36    -- -106.00 125.00   0.00  100
  5  ω   -121.00 -73.00   0.50    0.36    -- -106.00  57.00   0.00   96
  6  ω   -121.00 -77.00   0.50    0.36    -- -106.00  57.00  60.00   88
  7  ω   -155.00 -90.00   0.50    0.36    -- -106.00 -19.00  90.00  130
  8  ω   -149.00-111.00   0.50    0.36    -- -106.00 -19.00 -30.00   76
  9  ω   -139.00 -95.00   0.50    0.36    -- -106.00 -96.00-109.00   88
 10  ω   -118.00 -71.00   0.50    0.09    --  -46.62-125.00  30.00   94
 11  ω   -177.00 -88.00   0.50    0.36    -- -106.00 -99.00 -60.00  178
 12  ω     72.00 120.00   0.50    0.09    --   46.62 125.00 -30.00   96
;
_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      -0.0569231000
_diffrn_orient_matrix_UB_12      0.0500340000
_diffrn_orient_matrix_UB_13      0.0021575000
_diffrn_orient_matrix_UB_21      0.0826654000
_diffrn_orient_matrix_UB_22      0.0858112000
_diffrn_orient_matrix_UB_23      0.0835295000
_diffrn_orient_matrix_UB_31      0.0368973000
_diffrn_orient_matrix_UB_32      0.0397377000
_diffrn_orient_matrix_UB_33      -0.1831726000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.503
_reflns_Friedel_fraction_full    0.539
_reflns_Friedel_fraction_max     0.513
_reflns_number_gt                644
_reflns_number_total             645
_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 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details 
;
 Flack x determined using 214 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     73
_refine_ls_number_reflns         645
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0366
_refine_ls_restrained_S_all      1.152
_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)+(0.0792P)²+0.5460P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1063
_refine_ls_wR_factor_ref         0.1063
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Sof(F1)=Sof(F2)=1-FVAR(1)
 Sof(H7A)=Sof(H7B)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C2(H2)
;
_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
C3 C 0.89406(15) -0.49872(15) -0.4259(4) 0.0240(6) Uani 1 1 d . . . . .
H3 H 0.954176 -0.472437 -0.382225 0.029 Uiso 1 1 calc R U . . .
C6 C 0.71969(15) -0.56912(15) -0.5723(3) 0.0201(6) Uani 1 1 d . . . . .
C5 C 0.76452(16) -0.62074(16) -0.5722(3) 0.0205(6) Uani 1 1 d . . . . .
C1 C 0.75800(15) -0.48258(15) -0.4914(4) 0.0211(6) Uani 1 1 d . . . . .
C4 C 0.85017(15) -0.58974(17) -0.4909(3) 0.0221(6) Uani 1 1 d . . . . .
C7 C 0.67679(16) -0.46421(16) -0.4542(3) 0.0241(6) Uani 1 1 d . . . A 1
H7A H 0.677842 -0.445252 -0.333902 0.029 Uiso 0.964(6) 1 calc R U P B 1
H7B H 0.679154 -0.416843 -0.531458 0.029 Uiso 0.964(6) 1 calc R U P B 1
C2 C 0.84790(16) -0.44562(16) -0.4255(3) 0.0240(6) Uani 1 1 d . . . . .
H2 H 0.878257 -0.385572 -0.380778 0.029 Uiso 1 1 calc R U . . .
F1 F 0.674(3) -0.436(3) -0.300(6) 0.033(13) Uiso 0.036(6) 1 d . . P B 2
F2 F 0.688(3) -0.388(3) -0.572(5) 0.027(12) Uiso 0.036(6) 1 d . . P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C3 H3 0.9300 . ?
C3 C4 1.402(3) . ?
C3 C2 1.430(3) . ?
C6 C5 1.426(3) 2_535 ?
C6 C5 1.390(3) . ?
C6 C1 1.394(3) . ?
C5 C4 1.395(3) . ?
C1 C7 1.552(3) . ?
C1 C2 1.395(3) . ?
C4 C7 1.552(3) 3_755 ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C2 H2 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 C3 H3 119.5 . . ?
C4 C3 C2 121.1(2) . . ?
C2 C3 H3 119.5 . . ?
C5 C6 C5 120.3(2) . 2_535 ?
C5 C6 C1 121.8(2) . . ?
C1 C6 C5 111.0(2) . 2_535 ?
C6 C5 C6 119.7(2) . 3_755 ?
C6 C5 C4 122.4(2) . . ?
C4 C5 C6 111.0(2) . 3_755 ?
C6 C1 C7 106.9(2) . . ?
C6 C1 C2 116.8(2) . . ?
C2 C1 C7 133.8(2) . . ?
C3 C4 C7 134.5(2) . 3_755 ?
C5 C4 C3 116.2(2) . . ?
C5 C4 C7 106.94(19) . 3_755 ?
C1 C7 H7A 111.2 . . ?
C1 C7 H7B 111.2 . . ?
C4 C7 C1 102.76(17) 2_535 . ?
C4 C7 H7A 111.2 2_535 . ?
C4 C7 H7B 111.2 2_535 . ?
H7A C7 H7B 109.1 . . ?
C3 C2 H2 119.5 . . ?
C1 C2 C3 121.0(2) . . ?
C1 C2 H2 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C5 C4 C3 -157.7(2) 3_755 . . . ?
C6 C5 C4 C3 -7.0(3) . . . . ?
C6 C5 C4 C7 7.5(3) 3_755 . . 3_755 ?
C6 C5 C4 C7 158.2(2) . . . 3_755 ?
C6 C1 C7 C4 11.2(3) . . . 2_535 ?
C6 C1 C2 C3 -6.2(4) . . . . ?
C5 C6 C5 C6 0.1(5) 2_535 . . 3_755 ?
C5 C6 C5 C4 -148.1(2) 2_535 . . . ?
C5 C6 C1 C7 -158.4(2) . . . . ?
C5 C6 C1 C7 -7.4(3) 2_535 . . . ?
C5 C6 C1 C2 6.4(4) . . . . ?
C5 C6 C1 C2 157.4(2) 2_535 . . . ?
C1 C6 C5 C6 148.5(2) . . . 3_755 ?
C1 C6 C5 C4 0.3(4) . . . . ?
C4 C3 C2 C1 -0.5(4) . . . . ?
C7 C1 C2 C3 153.4(3) . . . . ?
C2 C3 C4 C5 7.1(4) . . . . ?
C2 C3 C4 C7 -152.9(3) . . . 3_755 ?
C2 C1 C7 C4 -149.9(3) . . . 2_535 ?

_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 1.440
_oxdiff_exptl_absorpt_empirical_full_min 0.525
####################################################################### 
# 
# 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_crystal-4
_database_code_depnum_ccdc_archive 'CCDC 2172508'
loop_
_audit_author_name
_audit_author_address
'Yumi Yakiyama'
;Osaka University
Japan
;
_audit_update_record             
;
2022-05-13 deposited with the CCDC.	2022-07-11 downloaded from the CCDC.
;
_audit_creation_date             2022-05-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H3.533, 0.467(F)'
_chemical_formula_sum            'C7 H3.53 F0.47'
_chemical_formula_weight         96.50
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      trigonal
_space_group_IT_number           161
_space_group_name_H-M_alt        'R 3 c'
_space_group_name_Hall           'R 3 -2"c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-y, -x, z+1/2'
'-x+y, y, z+1/2'
'x, x-y, z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'-y+2/3, -x+1/3, z+5/6'
'-x+y+2/3, y+1/3, z+5/6'
'x+2/3, x-y+1/3, z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-y+1/3, -x+2/3, z+7/6'
'-x+y+1/3, y+2/3, z+7/6'
'x+1/3, x-y+2/3, z+7/6'

_cell_length_a                   16.7127(9)
_cell_length_b                   16.7127(9)
_cell_length_c                   7.8468(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1898.1(2)
_cell_formula_units_Z            18
_cell_measurement_reflns_used    2822
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      31.0010
_cell_measurement_theta_min      2.4180
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61580
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             895
_exptl_crystal_size_max          0.348
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.070
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.847
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3885
_diffrn_reflns_point_group_measured_fraction_full 0.909
_diffrn_reflns_point_group_measured_fraction_max 0.730
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.793
_diffrn_reflns_theta_min         2.437
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.847
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -3.00  70.00   0.50   13.63    --   -5.49  30.00 -23.00  146
  2  ω    -10.00  21.00   0.50   13.63    --    5.65 101.00  87.00   62
  3  ω    -18.00   8.00   0.50   13.63    --   -5.49 -99.00 -60.00   52
  4  ω    -26.00  28.00   0.50   13.63    --   -5.49 -99.00-180.00  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      0.0379455000
_diffrn_orient_matrix_UB_12      0.0229790000
_diffrn_orient_matrix_UB_13      0.0565505000
_diffrn_orient_matrix_UB_21      0.0271870000
_diffrn_orient_matrix_UB_22      0.0293726000
_diffrn_orient_matrix_UB_23      -0.0672494000
_diffrn_orient_matrix_UB_31      -0.0148508000
_diffrn_orient_matrix_UB_32      0.0317753000
_diffrn_orient_matrix_UB_33      0.0212347000
_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         0.710
_reflns_Friedel_fraction_full    0.815
_reflns_Friedel_fraction_max     0.612
_reflns_number_gt                944
_reflns_number_total             973
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 369 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     83
_refine_ls_number_reflns         973
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0355
_refine_ls_restrained_S_all      1.059
_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)+(0.0687P)²+0.4753P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0973
_refine_ls_wR_factor_ref         0.0987
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Sof(H7A)=Sof(H7B)=1-FVAR(1)
 Sof(F1)=Sof(F2)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C2(H2)
;
_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
C6 C -0.28031(13) -0.56967(15) -0.5739(3) 0.0250(4) Uani 1 1 d . . . . .
C1 C -0.24235(14) -0.48398(14) -0.4929(3) 0.0265(5) Uani 1 1 d . . . . .
C3 C -0.10767(14) -0.50040(14) -0.4267(3) 0.0296(5) Uani 1 1 d . . . . .
H3 H -0.048339 -0.474797 -0.382012 0.036 Uiso 1 1 calc R U . . .
C5 C -0.23615(13) -0.62092(13) -0.5734(3) 0.0246(4) Uani 1 1 d . . . . .
C7 C -0.32312(15) -0.46561(14) -0.4583(3) 0.0301(5) Uani 1 1 d . . . A 1
H7A H -0.320504 -0.418629 -0.534397 0.036 Uiso 0.767(5) 1 calc R U P B 1
H7B H -0.322218 -0.446350 -0.341324 0.036 Uiso 0.767(5) 1 calc R U P B 1
C4 C -0.15090(12) -0.59004(14) -0.4936(3) 0.0272(5) Uani 1 1 d . . . . .
C2 C -0.15363(14) -0.44796(14) -0.4263(3) 0.0303(5) Uani 1 1 d . . . . .
H2 H -0.123860 -0.388633 -0.380812 0.036 Uiso 1 1 calc R U . . .
F1 F -0.3232(3) -0.4354(3) -0.3097(7) 0.0282(15) Uani 0.233(5) 1 d . . P B 2
F2 F -0.3147(4) -0.3953(3) -0.5753(8) 0.0320(16) Uani 0.233(5) 1 d . . P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C6 C1 1.396(3) . ?
C6 C5 1.382(3) . ?
C6 C5 1.431(3) 2_445 ?
C1 C7 1.551(3) . ?
C1 C2 1.393(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.400(3) . ?
C3 C2 1.425(3) . ?
C5 C4 1.397(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C4 1.551(3) 2_445 ?
C2 H2 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 C6 C5 110.86(18) . 2_445 ?
C5 C6 C1 121.65(18) . . ?
C5 C6 C5 120.1(2) . 2_445 ?
C6 C1 C7 106.79(17) . . ?
C2 C1 C6 116.97(18) . . ?
C2 C1 C7 133.8(2) . . ?
C4 C3 H3 119.7 . . ?
C4 C3 C2 120.69(18) . . ?
C2 C3 H3 119.7 . . ?
C6 C5 C6 119.9(2) . 3_545 ?
C6 C5 C4 122.30(19) . . ?
C4 C5 C6 110.99(18) . 3_545 ?
C1 C7 H7A 111.2 . . ?
C1 C7 H7B 111.2 . . ?
C1 C7 C4 103.05(15) . 2_445 ?
H7A C7 H7B 109.1 . . ?
C4 C7 H7A 111.2 2_445 . ?
C4 C7 H7B 111.2 2_445 . ?
C3 C4 C7 134.0(2) . 3_545 ?
C5 C4 C3 116.65(17) . . ?
C5 C4 C7 106.69(17) . 3_545 ?
C1 C2 C3 121.19(19) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C7 C4 12.3(3) . . . 2_445 ?
C6 C1 C2 C3 -5.9(3) . . . . ?
C6 C5 C4 C3 -156.55(19) 3_545 . . . ?
C6 C5 C4 C3 -5.6(3) . . . . ?
C6 C5 C4 C7 158.44(19) . . . 3_545 ?
C6 C5 C4 C7 7.5(2) 3_545 . . 3_545 ?
C1 C6 C5 C6 147.84(18) . . . 3_545 ?
C1 C6 C5 C4 -0.6(3) . . . . ?
C5 C6 C1 C7 -8.5(3) 2_445 . . . ?
C5 C6 C1 C7 -158.43(18) . . . . ?
C5 C6 C1 C2 6.4(3) . . . . ?
C5 C6 C1 C2 156.3(2) 2_445 . . . ?
C5 C6 C5 C6 0.6(4) 2_445 . . 3_545 ?
C5 C6 C5 C4 -147.83(17) 2_445 . . . ?
C7 C1 C2 C3 153.8(2) . . . . ?
C4 C3 C2 C1 -0.3(3) . . . . ?
C2 C1 C7 C4 -148.8(2) . . . 2_445 ?
C2 C3 C4 C5 6.0(3) . . . . ?
C2 C3 C4 C7 -152.6(2) . . . 3_545 ?

_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 2.058
_oxdiff_exptl_absorpt_empirical_full_min 0.470
####################################################################### 
# 
# 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_crystal-6
_database_code_depnum_ccdc_archive 'CCDC 2172515'
loop_
_audit_author_name
_audit_author_address
'Yumi Yakiyama'
;Osaka University
Japan
;
_audit_update_record             
;
2022-05-13 deposited with the CCDC.	2022-07-11 downloaded from the CCDC.
;
_audit_creation_date             2022-05-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H11.863, 0.137(F)'
_chemical_formula_sum            'C21 H11.86 F0.14'
_chemical_formula_weight         266.76
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      trigonal
_space_group_IT_number           161
_space_group_name_H-M_alt        'R 3 c'
_space_group_name_Hall           'R 3 -2"c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-y, -x, z+1/2'
'-x+y, y, z+1/2'
'x, x-y, z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'-y+2/3, -x+1/3, z+5/6'
'-x+y+2/3, y+1/3, z+5/6'
'x+2/3, x-y+1/3, z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-y+1/3, -x+2/3, z+7/6'
'-x+y+1/3, y+2/3, z+7/6'
'x+1/3, x-y+2/3, z+7/6'

_cell_length_a                   16.5968(5)
_cell_length_b                   16.5968(5)
_cell_length_c                   7.6249(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1818.92(13)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    5738
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      30.6200
_cell_measurement_theta_min      2.4350
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77207
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             835
_exptl_crystal_size_max          0.304
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.087
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.902
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6616
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.858
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.692
_diffrn_reflns_theta_min         2.454
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.902
_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  27.00   0.50   12.98    --    5.18 -79.00 -10.00  186
  2  ω    -10.00  30.00   0.50   12.98    --    5.18 -99.00  60.00   80
  3  ω    -19.00   7.00   0.50   12.98    --   -5.26 -99.00 120.00   52
  4  ω    -77.00 -36.00   0.50   12.98    --   -5.26 -71.00 104.00   82
  5  ω    -26.00  37.00   0.50   12.98    --    5.18 -99.00 -90.00  126
  6  ω    -26.00  26.00   0.50   12.98    --   -5.26 -99.00-150.00  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      0.0386890000
_diffrn_orient_matrix_UB_12      0.0333000000
_diffrn_orient_matrix_UB_13      0.0491883000
_diffrn_orient_matrix_UB_21      -0.0072004000
_diffrn_orient_matrix_UB_22      -0.0347828000
_diffrn_orient_matrix_UB_23      0.0620887000
_diffrn_orient_matrix_UB_31      0.0297800000
_diffrn_orient_matrix_UB_32      -0.0107852000
_diffrn_orient_matrix_UB_33      -0.0487537000
_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         0.885
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.812
_reflns_number_gt                1070
_reflns_number_total             1080
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 498 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.9(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     73
_refine_ls_number_reflns         1080
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0344
_refine_ls_restrained_S_all      1.121
_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)+(0.0709P)²+0.3313P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0958
_refine_ls_wR_factor_ref         0.0962
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Sof(H7A)=Sof(H7B)=1-FVAR(1)
 Sof(F1)=Sof(F2)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
3.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
C1 C -0.75801(11) -0.51755(11) -0.5080(3) 0.0169(4) Uani 1 1 d . . . . .
C2 C -0.71980(10) -0.43086(11) -0.4265(2) 0.0161(4) Uani 1 1 d . . . . .
C3 C -0.76460(11) -0.37935(11) -0.4268(2) 0.0162(4) Uani 1 1 d . . . . .
C4 C -0.85048(11) -0.41034(12) -0.5081(2) 0.0180(3) Uani 1 1 d . . . . .
C5 C -0.89441(11) -0.50143(11) -0.5736(2) 0.0194(4) Uani 1 1 d . . . . .
H5 H -0.954569 -0.527672 -0.617709 0.023 Uiso 1 1 calc R U . . .
C6 C -0.84831(11) -0.55467(11) -0.5736(2) 0.0196(4) Uani 1 1 d . . . . .
H6 H -0.878860 -0.614925 -0.618048 0.023 Uiso 1 1 calc R U . . .
C7 C -0.67688(12) -0.53606(11) -0.5453(2) 0.0198(4) Uani 1 1 d . . . A 1
H7A H -0.677910 -0.554943 -0.666088 0.024 Uiso 0.977(4) 1 calc R U P B 1
H7B H -0.679352 -0.583620 -0.467924 0.024 Uiso 0.977(4) 1 calc R U P B 1
F1 F -0.676(3) -0.565(3) -0.697(6) 0.028(14) Uiso 0.023(4) 1 d . . P B 2
F2 F -0.684(3) -0.615(3) -0.428(6) 0.025(14) Uiso 0.023(4) 1 d . . P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.395(2) . ?
C1 C6 1.398(2) . ?
C1 C7 1.550(2) . ?
C2 C3 1.385(2) . ?
C2 C3 1.427(2) 2_455 ?
C3 C4 1.395(2) . ?
C4 C5 1.401(2) . ?
C4 C7 1.551(2) 3_445 ?
C5 H5 0.9300 . ?
C5 C6 1.429(2) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 116.65(15) . . ?
C2 C1 C7 107.12(14) . . ?
C6 C1 C7 133.88(16) . . ?
C1 C2 C3 110.81(15) . 2_455 ?
C3 C2 C1 121.88(15) . . ?
C3 C2 C3 120.34(17) . 2_455 ?
C2 C3 C2 119.65(17) . 3_445 ?
C2 C3 C4 122.54(15) . . ?
C4 C3 C2 110.99(15) . 3_445 ?
C3 C4 C5 116.13(15) . . ?
C3 C4 C7 106.97(14) . 3_445 ?
C5 C4 C7 134.48(16) . 3_445 ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 121.10(14) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 121.00(14) . . ?
C1 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C1 C7 C4 102.73(12) . 2_455 ?
C1 C7 H7A 111.2 . . ?
C1 C7 H7B 111.2 . . ?
C4 C7 H7A 111.2 2_455 . ?
C4 C7 H7B 111.2 2_455 . ?
H7A C7 H7B 109.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C2 -148.46(14) . . . 3_445 ?
C1 C2 C3 C4 0.0(3) . . . . ?
C2 C1 C6 C5 6.6(3) . . . . ?
C2 C1 C7 C4 -11.1(2) . . . 2_455 ?
C2 C3 C4 C5 157.65(15) 3_445 . . . ?
C2 C3 C4 C5 6.8(2) . . . . ?
C2 C3 C4 C7 -158.14(15) . . . 3_445 ?
C2 C3 C4 C7 -7.28(19) 3_445 . . 3_445 ?
C3 C2 C3 C2 -0.4(3) 2_455 . . 3_445 ?
C3 C2 C3 C4 148.09(14) 2_455 . . . ?
C3 C4 C5 C6 -6.8(2) . . . . ?
C4 C5 C6 C1 0.2(2) . . . . ?
C6 C1 C2 C3 -157.54(15) . . . 2_455 ?
C6 C1 C2 C3 -6.7(3) . . . . ?
C6 C1 C7 C4 150.19(18) . . . 2_455 ?
C7 C1 C2 C3 7.5(2) . . . 2_455 ?
C7 C1 C2 C3 158.29(14) . . . . ?
C7 C1 C6 C5 -153.38(18) . . . . ?
C7 C4 C5 C6 152.83(18) 3_445 . . . ?

_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 1.334
_oxdiff_exptl_absorpt_empirical_full_min 0.677
####################################################################### 
# 
# 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_crystal-14
_database_code_depnum_ccdc_archive 'CCDC 2172513'
loop_
_audit_author_name
_audit_author_address
'Yumi Yakiyama'
;Osaka University
Japan
;
_audit_update_record             
;
2022-05-13 deposited with the CCDC.	2022-07-11 downloaded from the CCDC.
;
_audit_creation_date             2022-05-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H11.191, 0.809(F)'
_chemical_formula_sum            'C21 H11.19 F0.81'
_chemical_formula_weight         278.85
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      trigonal
_space_group_IT_number           161
_space_group_name_H-M_alt        'R 3 c'
_space_group_name_Hall           'R 3 -2"c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-y, -x, z+1/2'
'-x+y, y, z+1/2'
'x, x-y, z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'-y+2/3, -x+1/3, z+5/6'
'-x+y+2/3, y+1/3, z+5/6'
'x+2/3, x-y+1/3, z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-y+1/3, -x+2/3, z+7/6'
'-x+y+1/3, y+2/3, z+7/6'
'x+1/3, x-y+2/3, z+7/6'

_cell_length_a                   16.6650(5)
_cell_length_b                   16.6650(5)
_cell_length_c                   7.7508(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1864.18(13)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    2240
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      74.2170
_cell_measurement_theta_min      5.2980
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.740
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78435
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             867
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_av_unetI/netI     0.0160
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2778
_diffrn_reflns_point_group_measured_fraction_full 0.704
_diffrn_reflns_point_group_measured_fraction_max 0.690
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.489
_diffrn_reflns_theta_min         5.309
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'CCD plate'
_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  55.00   0.50    1.80    --   70.50 -10.00-176.00   92
  2  ω    -24.00  60.00   0.50    0.45    --   46.62 -57.00  30.00  168
  3  ω    -98.00 -59.00   0.50    1.80    -- -106.00  57.00-180.00   78
  4  ω    -55.00 -30.00   0.50    1.80    -- -106.00  19.00-150.00   50
  5  ω    -62.00 -34.00   0.50    1.80    -- -106.00 125.00-150.00   56
  6  ω   -113.00 -68.00   0.50    1.80    -- -106.00 125.00-150.00   90
  7  ω   -118.00 -89.00   0.50    1.80    -- -106.00  19.00-150.00   58
  8  ω   -120.00 -55.00   0.50    1.80    -- -106.00  37.00   0.00  130
  9  ω   -111.00 -57.00   0.50    1.80    -- -106.00 125.00  30.00  108
 10  ω   -109.00 -33.00   0.50    1.80    -- -106.00 120.00 159.00  152
 11  ω   -166.00 -76.00   0.50    1.80    -- -106.00-118.00  52.00  180
 12  ω   -114.00 -82.00   0.50    0.45    --  -46.62-125.00 -60.00   64
 13  ω   -161.00-136.00   0.50    1.80    -- -106.00-125.00 -90.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1025312000
_diffrn_orient_matrix_UB_12      0.0770115000
_diffrn_orient_matrix_UB_13      -0.0006332000
_diffrn_orient_matrix_UB_21      0.0294285000
_diffrn_orient_matrix_UB_22      -0.0733001000
_diffrn_orient_matrix_UB_23      -0.0266534000
_diffrn_orient_matrix_UB_31      -0.0042436000
_diffrn_orient_matrix_UB_32      0.0096848000
_diffrn_orient_matrix_UB_33      -0.1969083000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.364
_reflns_Friedel_fraction_full    0.402
_reflns_Friedel_fraction_max     0.372
_reflns_number_gt                596
_reflns_number_total             596
_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 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Flack x determined using 155 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     83
_refine_ls_number_reflns         596
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0327
_refine_ls_restrained_S_all      1.060
_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)+(0.0595P)²+0.8967P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0857
_refine_ls_wR_factor_ref         0.0857
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Sof(H7A)=Sof(H7B)=1-FVAR(1)
 Sof(F1)=Sof(F2)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
3.b Aromatic/amide H refined with riding coordinates:
 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
C1 C -0.75777(15) -0.51658(14) -0.5069(4) 0.0294(5) Uani 1 1 d . . . . .
C2 C -0.71965(14) -0.43064(14) -0.4263(3) 0.0278(5) Uani 1 1 d . . . . .
C3 C -0.76422(13) -0.37930(14) -0.4262(3) 0.0278(5) Uani 1 1 d . . . . .
C4 C -0.84950(14) -0.41031(15) -0.5070(3) 0.0292(5) Uani 1 1 d . . . . .
C5 C -0.89286(14) -0.50023(14) -0.5728(4) 0.0323(6) Uani 1 1 d . . . . .
H5 H -0.952528 -0.526021 -0.617259 0.039 Uiso 1 1 calc R U . . .
C6 C -0.84717(14) -0.55328(15) -0.5730(3) 0.0316(5) Uani 1 1 d . . . . .
H6 H -0.877375 -0.613070 -0.617713 0.038 Uiso 1 1 calc R U . . .
C7 C -0.67669(15) -0.53494(14) -0.5428(3) 0.0319(6) Uani 1 1 d . . . A 1
H7A H -0.677688 -0.554129 -0.661323 0.038 Uiso 0.865(5) 1 calc R U P B 1
H7B H -0.679109 -0.582045 -0.465989 0.038 Uiso 0.865(5) 1 calc R U P B 1
F1 F -0.6770(6) -0.5652(6) -0.6928(13) 0.030(3) Uani 0.135(5) 1 d . . P B 2
F2 F -0.6861(6) -0.6065(6) -0.4226(14) 0.033(3) Uani 0.135(5) 1 d . . P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.391(3) . ?
C1 C6 1.395(3) . ?
C1 C7 1.552(3) . ?
C2 C3 1.385(3) . ?
C2 C3 1.430(3) 2_455 ?
C3 C4 1.394(3) . ?
C4 C5 1.395(3) . ?
C4 C7 1.553(3) 3_445 ?
C5 H5 0.9300 . ?
C5 C6 1.426(3) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 117.0(2) . . ?
C2 C1 C7 106.80(18) . . ?
C6 C1 C7 133.8(2) . . ?
C1 C2 C3 111.10(19) . 2_455 ?
C3 C2 C1 121.7(2) . . ?
C3 C2 C3 120.2(2) . 2_455 ?
C2 C3 C2 119.8(2) . 3_445 ?
C2 C3 C4 122.2(2) . . ?
C4 C3 C2 110.9(2) . 3_445 ?
C3 C4 C5 116.54(18) . . ?
C3 C4 C7 106.76(18) . 3_445 ?
C5 C4 C7 134.2(2) . 3_445 ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 121.07(19) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 120.8(2) . . ?
C1 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C1 C7 C4 102.88(16) . 2_455 ?
C1 C7 H7A 111.2 . . ?
C1 C7 H7B 111.2 . . ?
C4 C7 H7A 111.2 2_455 . ?
C4 C7 H7B 111.2 2_455 . ?
H7A C7 H7B 109.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C2 -148.1(2) . . . 3_445 ?
C1 C2 C3 C4 -0.2(4) . . . . ?
C2 C1 C6 C5 6.2(4) . . . . ?
C2 C1 C7 C4 -11.8(3) . . . 2_455 ?
C2 C3 C4 C5 157.0(2) 3_445 . . . ?
C2 C3 C4 C5 6.5(3) . . . . ?
C2 C3 C4 C7 -158.2(2) . . . 3_445 ?
C2 C3 C4 C7 -7.8(3) 3_445 . . 3_445 ?
C3 C2 C3 C2 0.1(4) 2_455 . . 3_445 ?
C3 C2 C3 C4 147.98(19) 2_455 . . . ?
C3 C4 C5 C6 -6.4(3) . . . . ?
C4 C5 C6 C1 0.1(4) . . . . ?
C6 C1 C2 C3 -157.0(2) . . . 2_455 ?
C6 C1 C2 C3 -6.3(4) . . . . ?
C6 C1 C7 C4 149.4(3) . . . 2_455 ?
C7 C1 C2 C3 7.9(3) . . . 2_455 ?
C7 C1 C2 C3 158.6(2) . . . . ?
C7 C1 C6 C5 -153.5(3) . . . . ?
C7 C4 C5 C6 153.0(2) 3_445 . . . ?

_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 1.585
_oxdiff_exptl_absorpt_empirical_full_min 0.643
