# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 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_F2Sum-413K
_database_code_depnum_ccdc_archive 'CCDC 2119514'
loop_
_audit_author_name
_audit_author_address
'Yumi Yakiyama'
;Osaka University
Japan
;
_audit_update_record             
;
2021-11-01 deposited with the CCDC.	2022-04-08 downloaded from the CCDC.
;
_audit_creation_date             2021-11-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H10 F2'
_chemical_formula_sum            'C21 H10 F2'
_chemical_formula_weight         300.29
_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 0.0173 0.0100 '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                   16.872(2)
_cell_length_b                   16.872(2)
_cell_length_c                   8.1690(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     2013.9(7)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    20829
_cell_measurement_temperature    413(2)
_cell_measurement_theta_max      33.749
_cell_measurement_theta_min      0.401
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.740
_exptl_absorpt_correction_T_min  1.000
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'HKL3000sm Scalepack(Otwinowski et.al,2003)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             924
_exptl_crystal_size_max          0.424
_exptl_crystal_size_mid          0.179
_exptl_crystal_size_min          0.084
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0577
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.853
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7298
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.838
_diffrn_reflns_theta_full        24.835
_diffrn_reflns_theta_max         33.115
_diffrn_reflns_theta_min         4.387
_diffrn_ambient_temperature      413(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.853
_diffrn_measurement_device_type  'Rayonix MX225HS CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.700
_diffrn_source                   'PLSII 2D bending magnet'
_reflns_Friedel_coverage         0.951
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.823
_reflns_number_gt                1156
_reflns_number_total             1504
_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       'HKL3000sm (Otwinowski & Minor, 1997)'
_computing_data_collection       'PAL BL2D-SMDC Program (Shin et. al, 2016)'
_computing_data_reduction        'HKL3000sm (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 503 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         1504
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0580
_refine_ls_restrained_S_all      1.069
_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)+(0.1238P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1652
_refine_ls_wR_factor_ref         0.1816
_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
 Fixed Sof: H1A(0.66667) H1B(0.66667) F1(0.33333) F2(0.33333)
3.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4)
;
_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 0.46750(18) 0.3212(2) 0.4882(5) 0.0910(8) Uani 1 1 d . . . . .
H1A H 0.448370 0.319908 0.600580 0.109 Uiso 0.6667 1 calc R U P A 1
H1B H 0.420740 0.318371 0.415330 0.109 Uiso 0.6667 1 calc R U P A 1
C2 C 0.48606(18) 0.24218(19) 0.4543(5) 0.0820(7) Uani 1 1 d . . . B 1
C3 C 0.45161(18) 0.1553(2) 0.5191(5) 0.0920(8) Uani 1 1 d . . . B 1
H3 H 0.392997 0.125706 0.563501 0.110 Uiso 1 1 calc R U . B 1
C4 C 0.50375(19) 0.11043(17) 0.5193(5) 0.0915(8) Uani 1 1 d . . . B 1
H4 H 0.478844 0.051858 0.562895 0.110 Uiso 1 1 calc R U . B 1
C5 C 0.5920(2) 0.15342(16) 0.4546(4) 0.0822(7) Uani 1 1 d . . . B 1
C6 C 0.62194(16) 0.23732(17) 0.3772(3) 0.0732(6) Uani 1 1 d . . . B 1
C7 C 0.57085(17) 0.28003(16) 0.3763(3) 0.0737(6) Uani 1 1 d . . . B 1
F1 F 0.4373(4) 0.3214(4) 0.6304(8) 0.0973(14) Uani 0.3333 1 d . . P B 2
F2 F 0.3994(4) 0.3150(5) 0.3771(10) 0.1059(17) Uani 0.3333 1 d . . P B 2

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0696(12) 0.0979(18) 0.115(2) -0.0026(16) -0.0084(13) 0.0488(13)
C2 0.0589(10) 0.0811(14) 0.0996(19) -0.0069(10) -0.0133(11) 0.0302(9)
C3 0.0637(11) 0.0760(12) 0.115(2) -0.0077(13) -0.0065(12) 0.0187(10)
C4 0.0815(15) 0.0598(10) 0.114(2) -0.0061(11) -0.0060(13) 0.0208(10)
C5 0.0827(13) 0.0629(10) 0.0984(16) -0.0145(10) -0.0067(13) 0.0345(10)
C6 0.0712(11) 0.0674(11) 0.0792(12) -0.0118(10) -0.0060(8) 0.0333(8)
C7 0.0645(11) 0.0725(11) 0.0810(13) -0.0065(9) -0.0121(9) 0.0319(8)
F1 0.079(2) 0.112(4) 0.107(4) -0.008(3) 0.003(2) 0.052(3)
F2 0.075(3) 0.127(4) 0.127(4) -0.007(4) -0.022(3) 0.059(3)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.539(4) . ?
C1 C5 1.553(4) 3_665 ?
C1 F1 1.270(7) . ?
C1 F2 1.426(6) . ?
C2 C3 1.383(5) . ?
C2 C7 1.395(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.419(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.393(4) . ?
C5 C6 1.394(4) . ?
C6 C7 1.372(3) . ?
C6 C7 1.434(3) 2_655 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1A C1 H1B 109.0 . . ?
C2 C1 H1A 111.1 . . ?
C2 C1 H1B 111.1 . . ?
C2 C1 C5 103.4(2) . 3_665 ?
C5 C1 H1A 111.1 3_665 . ?
C5 C1 H1B 111.1 3_665 . ?
F1 C1 C5 112.4(4) . 3_665 ?
F1 C1 F2 105.8(4) . . ?
F2 C1 C5 111.2(4) . 3_665 ?
C3 C2 C1 133.6(3) . . ?
C3 C2 C7 116.8(3) . . ?
C7 C2 C1 107.0(2) . . ?
C2 C3 H3 119.3 . . ?
C2 C3 C4 121.4(3) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.5(3) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C1 134.1(3) . 2_655 ?
C4 C5 C6 116.8(3) . . ?
C6 C5 C1 106.3(2) . 2_655 ?
C5 C6 C7 111.1(2) . 2_655 ?
C7 C6 C5 122.1(2) . . ?
C7 C6 C7 119.9(3) . 2_655 ?
C2 C7 C6 110.6(2) . 3_665 ?
C6 C7 C2 121.8(2) . . ?
C6 C7 C6 120.1(3) . 3_665 ?

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 -153.1(3) . . . . ?
C1 C2 C7 C6 157.9(2) . . . . ?
C1 C2 C7 C6 8.4(3) . . . 3_665 ?
C1 C5 C6 C7 -7.7(3) 2_655 . . 2_655 ?
C1 C5 C6 C7 -158.5(2) 2_655 . . . ?
C2 C3 C4 C5 0.4(5) . . . . ?
C3 C2 C7 C6 -155.7(3) . . . 3_665 ?
C3 C2 C7 C6 -6.2(4) . . . . ?
C3 C4 C5 C1 152.5(3) . . . 2_655 ?
C3 C4 C5 C6 -5.9(4) . . . . ?
C4 C5 C6 C7 5.5(4) . . . . ?
C4 C5 C6 C7 156.4(3) . . . 2_655 ?
C5 C1 C2 C3 147.9(3) 3_665 . . . ?
C5 C1 C2 C7 -12.3(4) 3_665 . . . ?
C5 C6 C7 C2 0.6(4) . . . . ?
C5 C6 C7 C6 147.3(2) . . . 3_665 ?
C7 C2 C3 C4 5.6(5) . . . . ?
C7 C6 C7 C2 -147.8(2) 2_655 . . . ?
C7 C6 C7 C6 -1.1(5) 2_655 . . 3_665 ?

_shelx_res_file                  
;
TITL sample2_a.res in R3c
    sample2.res
    created by SHELXL-2018/3 at 18:06:13 on 01-Nov-2021
REM Old TITL sample2 in R3c
REM SHELXT solution in R3c: R1 0.148, Rweak 0.022, Alpha 0.014
REM <I/s> 0.483 for 47 systematic absences, Orientation as input
REM Flack x = -9.990 ( 9.990 ) from 411 Parsons' quotients
REM Formula found by SHELXT: C9
CELL 0.7 16.872 16.872 8.169 90 90 120
ZERR 6 0.0024 0.0024 0.0016 0 0 0
LATT -3
SYMM -Y,+X-Y,+Z
SYMM +Y-X,-X,+Z
SYMM -Y,-X,0.5+Z
SYMM +Y-X,+Y,0.5+Z
SYMM +X,+X-Y,0.5+Z
SFAC C H F
DISP C 0.0033 0.0016 11.1819
DISP F 0.0173 0.01 49.6179
DISP H -0 0 0.6234
UNIT 126 60 12

L.S. 8
PLAN  5
CONF
BOND
list 4
MORE -1
BOND $H
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\sample2.hkl">
REM </olex2.extras>

WGHT    0.123800
FVAR       0.94556
C1    1    0.467501    0.321214    0.488164    11.00000    0.06960    0.09789 =
         0.11494   -0.00262   -0.00839    0.04883
PART 1
AFIX  23
H1A   2    0.448370    0.319908    0.600580    10.66667   -1.20000
H1B   2    0.420740    0.318371    0.415330    10.66667   -1.20000
AFIX   0
C2    1    0.486059    0.242184    0.454342    11.00000    0.05894    0.08114 =
         0.09957   -0.00691   -0.01333    0.03017
C3    1    0.451605    0.155327    0.519106    11.00000    0.06367    0.07596 =
         0.11481   -0.00769   -0.00653    0.01868
AFIX  43
H3    2    0.392997    0.125706    0.563501    11.00000   -1.20000
AFIX   0
C4    1    0.503755    0.110431    0.519274    11.00000    0.08145    0.05983 =
         0.11390   -0.00608   -0.00604    0.02077
AFIX  43
H4    2    0.478844    0.051858    0.562895    11.00000   -1.20000
AFIX   0
C5    1    0.591972    0.153423    0.454601    11.00000    0.08268    0.06294 =
         0.09844   -0.01453   -0.00668    0.03448
C6    1    0.621939    0.237319    0.377230    11.00000    0.07122    0.06738 =
         0.07922   -0.01178   -0.00601    0.03333
C7    1    0.570849    0.280028    0.376307    11.00000    0.06447    0.07250 =
         0.08099   -0.00648   -0.01214    0.03191
PART 2
F1    3    0.437252    0.321410    0.630422    10.33333    0.07894    0.11152 =
         0.10717   -0.00813    0.00304    0.05182
F2    3    0.399412    0.314952    0.377096    10.33333    0.07545    0.12663 =
         0.12689   -0.00749   -0.02200    0.05893
HKLF 4




REM  sample2_a.res in R3c
REM wR2 = 0.1816, GooF = S = 1.070, Restrained GooF = 1.069 for all data
REM R1 = 0.0580 for 1156 Fo > 4sig(Fo) and 0.0666 for all 1504 data
REM 82 parameters refined using 1 restraints

END

WGHT      0.1238      0.0000

REM Highest difference peak  0.173,  deepest hole -0.220,  1-sigma level  0.035
Q1    1   0.4599  0.2780  0.5040  11.00000  0.05    0.17
Q2    1   0.5899  0.3261  0.3789  11.00000  0.05    0.16
Q3    1   0.5955  0.2523  0.3772  11.00000  0.05    0.15
Q4    1   0.4082  0.1301  0.6464  11.00000  0.05    0.13
Q5    1   0.4730  0.1955  0.4683  11.00000  0.05    0.13
;
_shelx_res_checksum              78950
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_F2Sum_100K
_database_code_depnum_ccdc_archive 'CCDC 2119515'
loop_
_audit_author_name
_audit_author_address
'Yumi Yakiyama'
;Osaka University
Japan
;
_audit_update_record             
;
2021-11-01 deposited with the CCDC.	2022-04-08 downloaded from the CCDC.
;
_audit_creation_date             2021-11-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H10 F2'
_chemical_formula_sum            'C21 H10 F2'
_chemical_formula_weight         300.29
_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 0.0009 0.0007 '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 0.0074 0.0047 '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                   16.735(2)
_cell_length_b                   16.735(2)
_cell_length_c                   7.8894(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1913.5(7)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    8460
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      38.00
_cell_measurement_theta_min      3.43
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.057
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8237
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             924
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9802
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        17.490
_diffrn_reflns_theta_max         18.959
_diffrn_reflns_theta_min         1.715
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'DECTRIS PILATUS3 X CdTM 1M Detector System'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'Si(311) double crystal monochromator'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.500900
_diffrn_source                   'SPring-8 BL02B1bending magnet'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.980
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                874
_reflns_number_total             972
_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       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        PROCESS-AUTO
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Flack x determined using 388 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         972
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0372
_refine_ls_restrained_S_all      1.036
_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)+(0.0733P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0964
_refine_ls_wR_factor_ref         0.0990
_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
 Fixed Sof: H1A(0.66667) H1B(0.66667) F1(0.33333) F2(0.33333)
3.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 -1.47635(18) -0.3429(2) -0.5158(4) 0.0329(6) Uani 1 1 d . . . . .
H1A H -1.457972 -0.343755 -0.399511 0.039 Uiso 0.6667 1 calc R U P A 2
H1B H -1.431957 -0.345313 -0.591508 0.039 Uiso 0.6667 1 calc R U P A 2
C2 C -1.48473(17) -0.25625(18) -0.5506(4) 0.0297(6) Uani 1 1 d . . . . .
C3 C -1.44209(17) -0.16770(18) -0.4833(4) 0.0318(6) Uani 1 1 d . . . . .
H3 H -1.383096 -0.142388 -0.437744 0.038 Uiso 1 1 calc R U . . .
C4 C -1.48789(19) -0.11536(18) -0.4834(3) 0.0314(6) Uani 1 1 d . . . . .
H4 H -1.458319 -0.056160 -0.437891 0.038 Uiso 1 1 calc R U . . .
C5 C -1.57598(19) -0.15128(19) -0.5502(4) 0.0292(6) Uani 1 1 d . . . . .
C6 C -1.61388(17) -0.23675(19) -0.6305(3) 0.0275(6) Uani 1 1 d . . . . .
C7 C -1.56963(17) -0.28726(17) -0.6304(3) 0.0270(6) Uani 1 1 d . . . . .
F1 F -1.4452(3) -0.3431(3) -0.3678(6) 0.0355(11) Uani 0.3333 1 d . . P B 1
F2 F -1.4136(3) -0.3511(3) -0.6303(7) 0.0386(11) Uani 0.3333 1 d . . P B 1

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0260(14) 0.0317(15) 0.0440(15) 0.0013(11) 0.0027(12) 0.0168(12)
C2 0.0242(12) 0.0290(13) 0.0372(14) 0.0038(11) 0.0067(11) 0.0144(11)
C3 0.0193(12) 0.0288(14) 0.0417(15) 0.0024(11) 0.0016(10) 0.0079(10)
C4 0.0261(12) 0.0202(12) 0.0409(14) 0.0009(10) 0.0034(10) 0.0063(10)
C5 0.0288(13) 0.0239(13) 0.0355(13) 0.0066(10) 0.0047(9) 0.0135(11)
C6 0.0265(13) 0.0266(14) 0.0270(12) 0.0058(10) 0.0036(9) 0.0115(11)
C7 0.0261(13) 0.0250(13) 0.0267(11) 0.0028(9) 0.0050(10) 0.0104(10)
F1 0.036(2) 0.035(2) 0.040(3) -0.0020(19) -0.007(2) 0.021(2)
F2 0.031(2) 0.044(3) 0.050(3) -0.002(2) 0.007(2) 0.025(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 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.549(4) . ?
C1 C5 1.553(4) 3_235 ?
C1 F1 1.279(6) . ?
C1 F2 1.443(6) . ?
C2 C3 1.389(4) . ?
C2 C7 1.395(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.423(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.388(4) . ?
C5 C6 1.394(4) . ?
C6 C7 1.374(3) . ?
C6 C7 1.434(3) 2_365 ?

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
H1A C1 H1B 109.1 . . ?
C2 C1 H1A 111.1 . . ?
C2 C1 H1B 111.1 . . ?
C2 C1 C5 103.4(2) . 3_235 ?
C5 C1 H1A 111.1 3_235 . ?
C5 C1 H1B 111.1 3_235 . ?
F1 C1 C2 113.1(3) . . ?
F1 C1 C5 114.5(4) . 3_235 ?
F1 C1 F2 104.7(4) . . ?
F2 C1 C2 112.9(3) . . ?
F2 C1 C5 108.4(3) . 3_235 ?
C3 C2 C1 133.8(3) . . ?
C3 C2 C7 117.0(2) . . ?
C7 C2 C1 106.5(2) . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.6(2) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 121.1(2) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C1 133.8(3) . 2_365 ?
C4 C5 C6 117.2(2) . . ?
C6 C5 C1 106.5(2) . 2_365 ?
C5 C6 C7 111.0(2) . 2_365 ?
C7 C6 C5 121.5(2) . . ?
C7 C6 C7 120.4(3) . 2_365 ?
C2 C7 C6 111.0(2) . 3_235 ?
C6 C7 C2 122.2(2) . . ?
C6 C7 C6 119.6(3) . 3_235 ?

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 -152.7(3) . . . . ?
C1 C2 C7 C6 7.9(3) . . . 3_235 ?
C1 C2 C7 C6 158.2(2) . . . . ?
C1 C5 C6 C7 -8.2(3) 2_365 . . 2_365 ?
C1 C5 C6 C7 -158.7(2) 2_365 . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
C3 C2 C7 C6 -5.6(4) . . . . ?
C3 C2 C7 C6 -155.9(2) . . . 3_235 ?
C3 C4 C5 C1 153.3(3) . . . 2_365 ?
C3 C4 C5 C6 -5.7(4) . . . . ?
C4 C5 C6 C7 5.7(4) . . . . ?
C4 C5 C6 C7 156.1(2) . . . 2_365 ?
C5 C1 C2 C3 147.7(3) 3_235 . . . ?
C5 C1 C2 C7 -12.1(3) 3_235 . . . ?
C5 C6 C7 C2 0.0(4) . . . . ?
C5 C6 C7 C6 147.8(2) . . . 3_235 ?
C7 C2 C3 C4 5.5(4) . . . . ?
C7 C6 C7 C2 -147.7(2) 2_365 . . . ?
C7 C6 C7 C6 0.1(5) 2_365 . . 3_235 ?
F1 C1 C2 C3 23.3(5) . . . . ?
F1 C1 C2 C7 -136.5(3) . . . . ?
F2 C1 C2 C3 -95.4(4) . . . . ?
F2 C1 C2 C7 104.8(3) . . . . ?

_shelx_res_file                  
;
TITL shelx2_a.res in R3c
    shelx2.res
    created by SHELXL-2018/3 at 18:05:37 on 01-Nov-2021
REM Old TITL shelx2 in R3c
REM SHELXT solution in R3c
REM R1 0.091, Rweak 0.017, Alpha 0.016, Orientation as input
REM Flack x = -9.990 ( 9.990 ) from Parsons' quotients
REM Formula found by SHELXT: C9
CELL 0.5009 16.735 16.735 7.8894 90 90 120
ZERR 6 0.0024 0.0024 0.0016 0 0 0
LATT -3
SYMM -Y,+X-Y,+Z
SYMM +Y-X,-X,+Z
SYMM -Y,-X,0.5+Z
SYMM +Y-X,+Y,0.5+Z
SYMM +X,+X-Y,0.5+Z
SFAC C H F
DISP C 0.0009 0.0007 6.328
DISP F 0.0074 0.0047 21.1287
DISP H -0 0 0.6081
UNIT 126 60 12

L.S. 8
PLAN  5
CONF
BOND $H
list 4
MORE -1
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\shelx2.hkl">
REM </olex2.extras>

WGHT    0.073300
FVAR       0.36441
C1    1   -1.476353   -0.342872   -0.515787    11.00000    0.02605    0.03172 =
         0.04398    0.00134    0.00275    0.01683
PART 2
AFIX  23
H1A   2   -1.457972   -0.343755   -0.399511    10.66667   -1.20000
H1B   2   -1.431957   -0.345313   -0.591508    10.66667   -1.20000
AFIX   0
PART 0
C2    1   -1.484726   -0.256253   -0.550613    11.00000    0.02416    0.02902 =
         0.03718    0.00384    0.00674    0.01435
C3    1   -1.442087   -0.167696   -0.483276    11.00000    0.01928    0.02884 =
         0.04165    0.00241    0.00156    0.00787
AFIX  43
H3    2   -1.383096   -0.142388   -0.437744    11.00000   -1.20000
AFIX   0
C4    1   -1.487886   -0.115363   -0.483360    11.00000    0.02607    0.02021 =
         0.04093    0.00090    0.00340    0.00635
AFIX  43
H4    2   -1.458319   -0.056160   -0.437891    11.00000   -1.20000
AFIX   0
C5    1   -1.575977   -0.151276   -0.550223    11.00000    0.02877    0.02389 =
         0.03546    0.00665    0.00468    0.01346
C6    1   -1.613880   -0.236752   -0.630500    11.00000    0.02649    0.02659 =
         0.02704    0.00576    0.00364    0.01153
C7    1   -1.569629   -0.287265   -0.630431    11.00000    0.02611    0.02498 =
         0.02668    0.00276    0.00499    0.01038
PART 1
F1    3   -1.445201   -0.343085   -0.367838    10.33333    0.03613    0.03538 =
         0.03955   -0.00195   -0.00724    0.02123
F2    3   -1.413602   -0.351103   -0.630342    10.33333    0.03068    0.04400 =
         0.04959   -0.00206    0.00659    0.02507
HKLF 4




REM  shelx2_a.res in R3c
REM wR2 = 0.0990, GooF = S = 1.037, Restrained GooF = 1.036 for all data
REM R1 = 0.0372 for 874 Fo > 4sig(Fo) and 0.0423 for all 972 data
REM 82 parameters refined using 1 restraints

END

WGHT      0.0733      0.0000

REM Highest difference peak  0.197,  deepest hole -0.166,  1-sigma level  0.041
Q1    1  -1.6623 -0.2617 -0.6347  11.00000  0.05    0.20
Q2    1  -1.5938 -0.1866 -0.6331  11.00000  0.05    0.16
Q3    1  -1.4663 -0.2864 -0.5291  11.00000  0.05    0.15
Q4    1  -1.4626 -0.0537 -0.3637  11.00000  0.05    0.14
Q5    1  -1.6039 -0.1362 -0.5317  11.00000  0.05    0.13
;
_shelx_res_checksum              90994
_olex2_submission_special_instructions 'No special instructions were received'
