# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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_wym240730
_database_code_depnum_ccdc_archive 'CCDC 2374591'
loop_
_audit_author_name
_audit_author_address
'Yumei Wang'
;jinan University
China
;
_audit_update_record             
;
2024-07-30 deposited with the CCDC.	2024-09-06 downloaded from the CCDC.
;
_audit_creation_date             2024-07-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H15 F O2'
_chemical_formula_sum            'C20 H15 F O2'
_chemical_formula_weight         306.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N '
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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.4867(3)
_cell_length_b                   9.8286(4)
_cell_length_c                   10.2689(5)
_cell_angle_alpha                104.731(4)
_cell_angle_beta                 100.536(4)
_cell_angle_gamma                100.806(3)
_cell_volume                     789.39(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3524
_cell_measurement_temperature    99.98(12)
_cell_measurement_theta_max      74.5740
_cell_measurement_theta_min      4.5850
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.738
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90730
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7587
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.262
_diffrn_reflns_theta_min         4.590
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(12)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -26.00  19.00   0.50    0.50    --    0.90  75.00 -72.00   90
  2  ω     52.00  78.00   0.50    1.55    --  105.10 -75.00 160.00   52
  3  ω     92.00 120.00   0.50    1.55    --  105.10 -75.00 160.00   56
  4  ω    126.00 152.00   0.50    1.55    --  105.10  75.00 -72.00   52
  5  ω     88.00 125.00   0.50    1.55    --  105.10  75.00 -72.00   74
  6  ω    -31.00  48.00   0.50    0.50    --   -0.90  77.00-150.00  158
  7  ω    -12.00  13.00   0.50    0.50    --   -0.90  75.00 -72.00   50
  8  ω    -37.00 -12.00   0.50    0.50    --    0.90 -75.00 160.00   50
  9  ω    -32.00  39.00   0.50    0.50    --    0.90  82.00  30.00  142
 10  ω     22.00  55.00   0.50    0.50    --    0.90  75.00 -72.00   66
 11  ω    -23.00  35.00   0.50    0.50    --    0.90  82.00   0.00  116
 12  ω     33.00 125.00   0.50    1.55    --  105.10 -38.00  60.00  184
 13  ω     79.00 192.00   0.50    1.55    --  105.10  19.00-120.00  226
 14  ω     18.00 111.00   0.50    1.55    --  105.10 -82.00-120.00  186
 15  ω     82.00 138.00   0.50    1.55    --  105.10 -82.00  60.00  112
 16  ω     17.00 104.00   0.50    1.55    --  105.10 -19.00 -30.00  174
 17  ω     99.00 194.00   0.50    1.55    --  105.10  82.00  90.00  190
 18  ω     39.00 136.00   0.50    1.55    --  105.10 -82.00   0.00  194
 19  ω     88.00 148.00   0.50    1.55    --  105.10  38.00-180.00  120
 20  ω     18.00  51.00   0.50    1.55    --  105.10 -82.00 -60.00   66
 21  ω     65.00 101.00   0.50    1.55    --  105.10 -77.00-180.00   72
 22  ω     85.00 110.00   0.50    1.55    --  105.10 -82.00 -60.00   50
 23  ω     19.00 116.00   0.50    1.55    --  105.10 -57.00 -30.00  194
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0644082000
_diffrn_orient_matrix_UB_12      0.0870862000
_diffrn_orient_matrix_UB_13      -0.0943371000
_diffrn_orient_matrix_UB_21      0.1175578000
_diffrn_orient_matrix_UB_22      -0.0425067000
_diffrn_orient_matrix_UB_23      -0.0925052000
_diffrn_orient_matrix_UB_31      -0.1353551000
_diffrn_orient_matrix_UB_32      -0.1362690000
_diffrn_orient_matrix_UB_33      -0.0900636000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2747
_reflns_number_total             3203
_reflns_odcompleteness_completeness 99.40
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0441
_refine_ls_restrained_S_all      1.104
_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)+(0.0655P)²+0.1518P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1222
_refine_ls_wR_factor_ref         0.1269
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00G(H00J)
2.b Secondary CH2 refined with riding coordinates:
 C006(H00A,H00B)
2.c Aromatic/amide H refined with riding coordinates:
 C00A(H00C), C00D(H00G), C00E(H00H), C00F(H00I), C00H(H00K), C00K(H00L),
 C00L(H00M), C00M(H00N), C00N(H00O)
2.d Idealised Me refined as rotating group:
 C00B(H00D,H00E,H00F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F001 F -0.25148(11) -0.03953(10) 0.31699(10) 0.0488(3) Uani 1 1 d . . . . .
O002 O 0.57690(13) 0.93903(11) 0.88912(10) 0.0394(3) Uani 1 1 d . . . . .
O003 O 0.70417(13) 1.04955(12) 0.75755(11) 0.0441(3) Uani 1 1 d . . . . .
C004 C 0.10047(16) 0.33904(15) 0.52729(15) 0.0338(3) Uani 1 1 d . . . . .
C005 C 0.21665(17) 0.47534(16) 0.59734(15) 0.0361(3) Uani 1 1 d . . . . .
C006 C 0.5157(2) 0.72341(17) 0.96550(16) 0.0429(4) Uani 1 1 d . . . . .
H00A H 0.540271 0.786595 1.062373 0.052 Uiso 1 1 calc R . . . .
H00B H 0.425939 0.637918 0.954574 0.052 Uiso 1 1 calc R . . . .
C007 C 0.66803(19) 0.67262(17) 0.94103(15) 0.0389(3) Uani 1 1 d . . . . .
C008 C 0.60949(17) 0.94561(16) 0.76528(15) 0.0360(3) Uani 1 1 d . . . . .
C009 C 0.51390(16) 0.81247(15) 0.65570(15) 0.0335(3) Uani 1 1 d . . . . .
C00A C 0.07635(18) 0.27909(16) 0.38427(15) 0.0383(3) Uani 1 1 d . . . . .
H00C H 0.141256 0.326954 0.335264 0.046 Uiso 1 1 calc R . . . .
C00B C 0.52004(18) 0.78582(16) 0.50791(15) 0.0381(3) Uani 1 1 d . . . . .
H00D H 0.460914 0.847702 0.467515 0.057 Uiso 1 1 calc GR . . . .
H00E H 0.467743 0.683676 0.456705 0.057 Uiso 1 1 calc GR . . . .
H00F H 0.635507 0.808490 0.501994 0.057 Uiso 1 1 calc GR . . . .
C00C C 0.42390(16) 0.72982(15) 0.71524(15) 0.0345(3) Uani 1 1 d . . . . .
C00D C 0.00780(17) 0.26497(16) 0.59887(16) 0.0367(3) Uani 1 1 d . . . . .
H00G H 0.026229 0.303070 0.696667 0.044 Uiso 1 1 calc R . . . .
C00E C 0.65487(19) 0.53383(16) 0.85545(15) 0.0395(3) Uani 1 1 d . . . . .
H00H H 0.548685 0.469588 0.813561 0.047 Uiso 1 1 calc R . . . .
C00F C 0.8258(2) 0.76357(18) 1.00181(16) 0.0442(4) Uani 1 1 d . . . . .
H00I H 0.837866 0.858358 1.061140 0.053 Uiso 1 1 calc R . . . .
C00G C 0.45485(18) 0.80655(15) 0.86775(16) 0.0385(3) Uani 1 1 d . . . . .
H00J H 0.350825 0.831471 0.887200 0.046 Uiso 1 1 calc R . . . .
C00H C -0.11024(18) 0.13696(16) 0.52867(16) 0.0377(3) Uani 1 1 d . . . . .
H00K H -0.173967 0.086645 0.576763 0.045 Uiso 1 1 calc R . . . .
C00I C -0.13301(17) 0.08428(16) 0.38712(16) 0.0373(3) Uani 1 1 d . . . . .
C00J C 0.31215(17) 0.59211(16) 0.65074(15) 0.0356(3) Uani 1 1 d . . . . .
C00K C -0.04064(19) 0.15126(17) 0.31365(16) 0.0407(3) Uani 1 1 d . . . . .
H00L H -0.057195 0.110238 0.216391 0.049 Uiso 1 1 calc R . . . .
C00L C 0.9658(2) 0.71786(19) 0.97702(17) 0.0474(4) Uani 1 1 d . . . . .
H00M H 1.072428 0.781014 1.019741 0.057 Uiso 1 1 calc R . . . .
C00M C 0.7944(2) 0.48815(18) 0.83055(16) 0.0448(4) Uani 1 1 d . . . . .
H00N H 0.783336 0.393049 0.772277 0.054 Uiso 1 1 calc R . . . .
C00N C 0.9500(2) 0.58073(19) 0.89036(17) 0.0470(4) Uani 1 1 d . . . . .
H00O H 1.045422 0.550002 0.871832 0.056 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F001 C00I 1.3569(16) . ?
O002 C008 1.3644(18) . ?
O002 C00G 1.4430(17) . ?
O003 C008 1.2051(18) . ?
C004 C005 1.428(2) . ?
C004 C00A 1.397(2) . ?
C004 C00D 1.399(2) . ?
C005 C00J 1.201(2) . ?
C006 H00A 0.9900 . ?
C006 H00B 0.9900 . ?
C006 C007 1.510(2) . ?
C006 C00G 1.526(2) . ?
C007 C00E 1.394(2) . ?
C007 C00F 1.394(2) . ?
C008 C009 1.468(2) . ?
C009 C00B 1.485(2) . ?
C009 C00C 1.345(2) . ?
C00A H00C 0.9500 . ?
C00A C00K 1.377(2) . ?
C00B H00D 0.9800 . ?
C00B H00E 0.9800 . ?
C00B H00F 0.9800 . ?
C00C C00G 1.505(2) . ?
C00C C00J 1.415(2) . ?
C00D H00G 0.9500 . ?
C00D C00H 1.381(2) . ?
C00E H00H 0.9500 . ?
C00E C00M 1.386(2) . ?
C00F H00I 0.9500 . ?
C00F C00L 1.389(2) . ?
C00G H00J 1.0000 . ?
C00H H00K 0.9500 . ?
C00H C00I 1.377(2) . ?
C00I C00K 1.376(2) . ?
C00K H00L 0.9500 . ?
C00L H00M 0.9500 . ?
C00L C00N 1.380(2) . ?
C00M H00N 0.9500 . ?
C00M C00N 1.384(2) . ?
C00N H00O 0.9500 . ?

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
C008 O002 C00G 109.55(11) . . ?
C00A C004 C005 119.67(13) . . ?
C00A C004 C00D 119.08(13) . . ?
C00D C004 C005 121.24(13) . . ?
C00J C005 C004 176.85(15) . . ?
H00A C006 H00B 107.7 . . ?
C007 C006 H00A 108.8 . . ?
C007 C006 H00B 108.8 . . ?
C007 C006 C00G 113.85(12) . . ?
C00G C006 H00A 108.8 . . ?
C00G C006 H00B 108.8 . . ?
C00E C007 C006 120.92(14) . . ?
C00E C007 C00F 117.99(15) . . ?
C00F C007 C006 121.09(14) . . ?
O002 C008 C009 109.33(12) . . ?
O003 C008 O002 121.09(13) . . ?
O003 C008 C009 129.58(14) . . ?
C008 C009 C00B 122.97(13) . . ?
C00C C009 C008 107.34(12) . . ?
C00C C009 C00B 129.67(13) . . ?
C004 C00A H00C 119.7 . . ?
C00K C00A C004 120.60(14) . . ?
C00K C00A H00C 119.7 . . ?
C009 C00B H00D 109.5 . . ?
C009 C00B H00E 109.5 . . ?
C009 C00B H00F 109.5 . . ?
H00D C00B H00E 109.5 . . ?
H00D C00B H00F 109.5 . . ?
H00E C00B H00F 109.5 . . ?
C009 C00C C00G 109.87(12) . . ?
C009 C00C C00J 127.85(13) . . ?
C00J C00C C00G 122.26(13) . . ?
C004 C00D H00G 119.7 . . ?
C00H C00D C004 120.62(14) . . ?
C00H C00D H00G 119.7 . . ?
C007 C00E H00H 119.5 . . ?
C00M C00E C007 120.97(14) . . ?
C00M C00E H00H 119.5 . . ?
C007 C00F H00I 119.5 . . ?
C00L C00F C007 121.08(15) . . ?
C00L C00F H00I 119.5 . . ?
O002 C00G C006 110.57(12) . . ?
O002 C00G C00C 103.84(11) . . ?
O002 C00G H00J 108.8 . . ?
C006 C00G H00J 108.8 . . ?
C00C C00G C006 115.69(12) . . ?
C00C C00G H00J 108.8 . . ?
C00D C00H H00K 120.9 . . ?
C00I C00H C00D 118.19(13) . . ?
C00I C00H H00K 120.9 . . ?
F001 C00I C00H 118.53(13) . . ?
F001 C00I C00K 118.53(13) . . ?
C00K C00I C00H 122.94(14) . . ?
C005 C00J C00C 179.25(16) . . ?
C00A C00K H00L 120.7 . . ?
C00I C00K C00A 118.50(14) . . ?
C00I C00K H00L 120.7 . . ?
C00F C00L H00M 120.0 . . ?
C00N C00L C00F 120.03(15) . . ?
C00N C00L H00M 120.0 . . ?
C00E C00M H00N 119.9 . . ?
C00N C00M C00E 120.19(15) . . ?
C00N C00M H00N 119.9 . . ?
C00L C00N C00M 119.73(16) . . ?
C00L C00N H00O 120.1 . . ?
C00M C00N H00O 120.1 . . ?


_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 1.227
_oxdiff_exptl_absorpt_empirical_full_min 0.838
