# Electronic Supplementary Material (ESI) for Organic 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_yangsh_210603
_database_code_depnum_ccdc_archive 'CCDC 2090736'
loop_
_audit_author_name
_audit_author_address
'Shuang Yang'
;Sun Yatsen university
China
;
_audit_update_record             
;
2021-06-18 deposited with the CCDC.	2022-07-08 downloaded from the CCDC.
;
_audit_creation_date             2021-06-07
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H12 F2 O2'
_chemical_formula_sum            'C13 H12 F2 O2'
_chemical_formula_weight         238.23
_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'
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                   4.0300(3)
_cell_length_b                   10.8122(9)
_cell_length_c                   12.5820(8)
_cell_angle_alpha                97.471(6)
_cell_angle_beta                 91.394(7)
_cell_angle_gamma                94.032(7)
_cell_volume                     541.93(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2068
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      71.2220
_cell_measurement_theta_min      3.5340
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.026
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75744
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
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    1.460
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_av_unetI/netI     0.0577
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.913
_diffrn_reflns_limit_h_max       2
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5032
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.619
_diffrn_reflns_theta_min         3.545
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.913
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    121.00 147.00   0.50    0.20    --  105.44  99.00  10.00   52
  2  ω     83.00 169.00   0.50    0.20    --  105.44  77.00-150.00  172
  3  ω    105.00 176.00   0.50    0.20    --  105.44  30.00 -60.00  142
  4  ω     35.00  60.00   0.50    0.20    --  105.44 -77.00  90.00   50
  5  ω     35.00  77.00   0.50    0.20    --  105.44 -77.00 150.00   84
  6  ω     81.00 107.00   0.50    0.20    --  105.44 -77.00 150.00   52
  7  ω    -26.00  45.00   0.50    0.05    --   46.37 -38.00  90.00  142
  8  ω    -28.00  -2.00   0.50    0.05    --   46.37 -19.00   0.00   52
  9  ω     36.00  87.00   0.50    0.20    --  105.44 -94.00 -90.00  102
 10  ω     70.00 111.00   0.50    0.20    --  105.44-125.00-150.00   82
 11  ω     81.00 111.00   0.50    0.20    --  105.44-125.00-120.00   60
 12  ω    -17.00  35.00   0.50    0.05    --   46.37 -99.00 -96.00  104
 13  ω     34.00  61.00   0.50    0.20    --  105.44-125.00-150.00   54
 14  ω     41.00  96.00   0.50    0.20    --  105.44 -99.00 -96.00  110
 15  ω     34.00 111.00   0.50    0.20    --  105.44-125.00  90.00  154
 16  ω    -40.00  22.00   0.50    0.05    --  -46.37  38.00 -90.00  124
 17  ω    -60.00 -35.00   0.50    0.05    --  -46.37  57.00 -30.00   50
 18  ω    -32.00  21.00   0.50    0.05    --  -46.37  57.00 -30.00  106
 19  ω    -21.00  14.00   0.50    0.05    --  -46.37  99.00  10.00   70
 20  ω    -72.00 -36.00   0.50    0.05    --  -46.37  99.00  10.00   72
 21  ω    -63.00 -30.00   0.50    0.20    -- -100.00 125.00 -30.00   66
 22  ω   -102.00 -68.00   0.50    0.20    -- -100.00 125.00 -30.00   68
 23  ω    -52.00 -27.00   0.50    0.20    -- -100.00 116.00 140.04   50
 24  ω   -109.00 -84.00   0.50    0.20    -- -100.00 116.00 140.04   50
 25  ω    -66.00 -41.00   0.50    0.20    -- -100.00  99.00  10.00   50
 26  ω    -92.00 -32.00   0.50    0.20    -- -100.00  77.00   0.00  120
 27  ω    -66.00 -31.00   0.50    0.20    -- -100.00  61.00 -30.00   70
 28  ω    -54.00 -29.00   0.50    0.20    -- -100.00  77.00-180.00   50
 29  ω   -101.00 -73.00   0.50    0.20    -- -100.00  77.00-180.00   56
 30  ω   -145.00 -99.00   0.50    0.20    -- -100.00 -99.00 -96.00   92
 31  ω   -161.00-135.00   0.50    0.20    -- -100.00 -94.00-150.00   52
 32  ω   -125.00 -84.00   0.50    0.20    -- -100.00 -94.00-150.00   82
 33  ω   -130.00 -90.00   0.50    0.20    -- -100.00 -94.00-120.00   80
 34  ω   -166.00 -98.00   0.50    0.20    -- -100.00 -45.00 120.00  136
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1477989000
_diffrn_orient_matrix_UB_12      0.0937871000
_diffrn_orient_matrix_UB_13      0.0855239000
_diffrn_orient_matrix_UB_21      -0.0016653000
_diffrn_orient_matrix_UB_22      0.0966772000
_diffrn_orient_matrix_UB_23      -0.0797645000
_diffrn_orient_matrix_UB_31      -0.3538028000
_diffrn_orient_matrix_UB_32      -0.0512103000
_diffrn_orient_matrix_UB_33      -0.0398821000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1700
_reflns_number_total             2080
_reflns_odcompleteness_completeness 98.86
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (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         0.731
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2080
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0740
_refine_ls_R_factor_gt           0.0639
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1228P)²+0.1022P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1817
_refine_ls_wR_factor_ref         0.1936
_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:
 C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C2(H2), C3(H3), C6(H6)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_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
F8 F 0.5906(3) 0.17157(12) 0.16634(11) 0.0346(4) Uani 1 1 d . . . . .
F17 F 0.8014(3) 0.35092(13) 0.50555(11) 0.0346(4) Uani 1 1 d . . . . .
O10 O 0.1798(4) 0.75892(15) 0.09240(14) 0.0335(4) Uani 1 1 d . . . . .
O12 O 0.3887(4) 0.84378(15) 0.25453(15) 0.0368(4) Uani 1 1 d . . . . .
C4 C 0.4292(5) 0.6252(2) 0.19960(18) 0.0269(5) Uani 1 1 d . . . . .
C13 C 0.8546(5) 0.2223(2) 0.33108(19) 0.0280(5) Uani 1 1 d . . . . .
C1 C 0.6029(5) 0.3874(2) 0.23273(18) 0.0269(5) Uani 1 1 d . . . . .
C5 C 0.6134(5) 0.6094(2) 0.29104(19) 0.0292(5) Uani 1 1 d . . . . .
H5 H 0.678332 0.678313 0.341245 0.035 Uiso 1 1 calc R U . . .
C9 C 0.3344(5) 0.7536(2) 0.18763(19) 0.0299(5) Uani 1 1 d . . . . .
C2 C 0.4215(5) 0.4039(2) 0.14037(19) 0.0297(5) Uani 1 1 d . . . . .
H2 H 0.357857 0.335419 0.089607 0.036 Uiso 1 1 calc R U . . .
C3 C 0.3356(5) 0.5223(2) 0.12399(19) 0.0310(5) Uani 1 1 d . . . . .
H3 H 0.215127 0.532760 0.062232 0.037 Uiso 1 1 calc R U . . .
C7 C 0.6934(5) 0.2615(2) 0.24980(18) 0.0280(5) Uani 1 1 d . . . . .
C16 C 1.0101(5) 0.2823(2) 0.43755(19) 0.0303(5) Uani 1 1 d . . . . .
H16 H 1.221989 0.329640 0.428917 0.036 Uiso 1 1 calc R U . . .
C6 C 0.7010(5) 0.4915(2) 0.30798(19) 0.0300(5) Uani 1 1 d . . . . .
H6 H 0.824832 0.481608 0.369249 0.036 Uiso 1 1 calc R U . . .
C15 C 1.0614(5) 0.1516(2) 0.4673(2) 0.0326(5) Uani 1 1 d . . . . .
H15A H 0.913221 0.126664 0.521562 0.039 Uiso 1 1 calc R U . . .
H15B H 1.290679 0.139380 0.485845 0.039 Uiso 1 1 calc R U . . .
C14 C 0.9502(5) 0.0935(2) 0.3510(2) 0.0327(5) Uani 1 1 d . . . . .
H14A H 1.130445 0.062803 0.307666 0.039 Uiso 1 1 calc R U . . .
H14B H 0.763440 0.031244 0.347279 0.039 Uiso 1 1 calc R U . . .
C11 C 0.0799(6) 0.8808(2) 0.0756(2) 0.0360(6) Uani 1 1 d . . . . .
H11A H -0.015937 0.876772 0.004510 0.054 Uiso 1 1 calc R U . . .
H11B H 0.270754 0.940018 0.084001 0.054 Uiso 1 1 calc R U . . .
H11C H -0.081683 0.906757 0.127134 0.054 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
F8 C7 1.370(3) . ?
F17 C16 1.396(2) . ?
O10 C9 1.347(3) . ?
O10 C11 1.445(3) . ?
O12 C9 1.206(3) . ?
C4 C5 1.390(3) . ?
C4 C9 1.491(3) . ?
C4 C3 1.391(3) . ?
C13 C7 1.329(3) . ?
C13 C16 1.511(3) . ?
C13 C14 1.520(3) . ?
C1 C2 1.396(3) . ?
C1 C7 1.474(3) . ?
C1 C6 1.401(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.388(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.388(3) . ?
C3 H3 0.9300 . ?
C16 H16 0.9800 . ?
C16 C15 1.534(3) . ?
C6 H6 0.9300 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C14 1.558(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?

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
C9 O10 C11 115.29(19) . . ?
C5 C4 C9 117.9(2) . . ?
C5 C4 C3 119.7(2) . . ?
C3 C4 C9 122.4(2) . . ?
C7 C13 C16 135.9(2) . . ?
C7 C13 C14 132.2(2) . . ?
C16 C13 C14 91.94(18) . . ?
C2 C1 C7 120.1(2) . . ?
C2 C1 C6 119.4(2) . . ?
C6 C1 C7 120.6(2) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.5(2) . . ?
C6 C5 H5 119.8 . . ?
O10 C9 C4 112.4(2) . . ?
O12 C9 O10 122.9(2) . . ?
O12 C9 C4 124.7(2) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.3(2) . . ?
C3 C2 H2 119.9 . . ?
C4 C3 H3 119.9 . . ?
C2 C3 C4 120.2(2) . . ?
C2 C3 H3 119.9 . . ?
F8 C7 C1 112.87(19) . . ?
C13 C7 F8 116.07(19) . . ?
C13 C7 C1 131.1(2) . . ?
F17 C16 C13 115.82(17) . . ?
F17 C16 H16 112.0 . . ?
F17 C16 C15 114.04(18) . . ?
C13 C16 H16 112.0 . . ?
C13 C16 C15 89.22(17) . . ?
C15 C16 H16 112.0 . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 120.0(2) . . ?
C5 C6 H6 120.0 . . ?
C16 C15 H15A 113.7 . . ?
C16 C15 H15B 113.7 . . ?
C16 C15 C14 89.65(18) . . ?
H15A C15 H15B 111.0 . . ?
C14 C15 H15A 113.7 . . ?
C14 C15 H15B 113.7 . . ?
C13 C14 C15 88.05(17) . . ?
C13 C14 H14A 114.0 . . ?
C13 C14 H14B 114.0 . . ?
C15 C14 H14A 114.0 . . ?
C15 C14 H14B 114.0 . . ?
H14A C14 H14B 111.2 . . ?
O10 C11 H11A 109.5 . . ?
O10 C11 H11B 109.5 . . ?
O10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

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
F17 C16 C15 C14 126.10(18) . . . . ?
C4 C5 C6 C1 -0.2(3) . . . . ?
C13 C16 C15 C14 8.01(15) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
C5 C4 C9 O10 175.12(16) . . . . ?
C5 C4 C9 O12 -4.7(3) . . . . ?
C5 C4 C3 C2 0.9(3) . . . . ?
C9 C4 C5 C6 178.23(17) . . . . ?
C9 C4 C3 C2 -178.03(17) . . . . ?
C2 C1 C7 F8 2.0(3) . . . . ?
C2 C1 C7 C13 -178.0(2) . . . . ?
C2 C1 C6 C5 1.0(3) . . . . ?
C3 C4 C5 C6 -0.8(3) . . . . ?
C3 C4 C9 O10 -5.9(3) . . . . ?
C3 C4 C9 O12 174.31(19) . . . . ?
C7 C13 C16 F17 54.9(3) . . . . ?
C7 C13 C16 C15 171.4(2) . . . . ?
C7 C13 C14 C15 -171.5(2) . . . . ?
C7 C1 C2 C3 179.98(17) . . . . ?
C7 C1 C6 C5 -179.83(17) . . . . ?
C16 C13 C7 F8 -179.6(2) . . . . ?
C16 C13 C7 C1 0.4(4) . . . . ?
C16 C13 C14 C15 8.09(15) . . . . ?
C16 C15 C14 C13 -7.97(15) . . . . ?
C6 C1 C2 C3 -0.8(3) . . . . ?
C6 C1 C7 F8 -177.26(16) . . . . ?
C6 C1 C7 C13 2.8(3) . . . . ?
C14 C13 C7 F8 -0.2(3) . . . . ?
C14 C13 C7 C1 179.78(19) . . . . ?
C14 C13 C16 F17 -124.70(19) . . . . ?
C14 C13 C16 C15 -8.21(15) . . . . ?
C11 O10 C9 O12 -0.4(3) . . . . ?
C11 O10 C9 C4 179.80(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.049
_oxdiff_exptl_absorpt_empirical_full_min 0.327
####################################################################### 
# 
# 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_yangsh_220407_auto
_database_code_depnum_ccdc_archive 'CCDC 2168796'
loop_
_audit_author_name
_audit_author_address
'Shuang Yang'
;Sun Yatsen university
China
;
_audit_update_record             
;
2022-04-26 deposited with the CCDC.	2022-07-08 downloaded from the CCDC.
;
_audit_creation_date             2022-04-08
_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         'C11 H9 F2 N O2'
_chemical_formula_sum            'C11 H9 F2 N O2'
_chemical_formula_weight         225.19
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNOF
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'
N N 0.0311 0.0180 '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                   6.1659(3)
_cell_length_b                   7.2541(4)
_cell_length_c                   10.9186(5)
_cell_angle_alpha                78.829(4)
_cell_angle_beta                 81.971(4)
_cell_angle_gamma                82.243(4)
_cell_volume                     471.48(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2573
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.3750
_cell_measurement_theta_min      6.2720
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.176
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.120a (Rigaku Oxford Diffraction, 2021)
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    1.586
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             232
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4220
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.031
_diffrn_reflns_theta_min         4.156
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     23.00  70.00   0.50    0.05    --   45.56 -77.00 -60.00   94
  2  ω     36.00  69.00   0.50    0.05    --  104.88 -61.00-120.00   66
  3  ω     35.00  73.00   0.50    0.05    --  104.88 -61.00 120.00   76
  4  ω    128.00 158.00   0.50    0.05    --  104.88 100.00   0.00   60
  5  ω     92.00 119.00   0.50    0.05    --  104.88 100.00   0.00   54
  6  ω    -49.00 -23.00   0.50    0.05    --  -45.56 100.00   0.00   52
  7  ω    -13.00  21.00   0.50    0.05    --  -45.56 100.00   0.00   68
  8  ω    -83.00 -46.00   0.50    0.05    -- -100.00 125.00   0.00   74
  9  ω    -89.00 -49.00   0.50    0.05    -- -100.00 100.00   0.00   80
 10  ω    -68.00 -27.00   0.50    0.05    -- -100.00  61.00  30.00   82
 11  ω    -40.00  24.00   0.50    0.05    --  -45.56  38.00  90.00  128
 12  ω    -40.00  27.00   0.50    0.05    --  -45.56  38.00-180.00  134
 13  ω    -62.00 -29.00   0.50    0.05    --  -45.56 -57.00 -60.00   66
 14  ω   -117.00 -77.00   0.50    0.05    --  -45.56 -57.00 -60.00   80
 15  ω   -137.00 -88.00   0.50    0.05    -- -100.00 -61.00 120.00   98
 16  ω   -109.00 -84.00   0.50    0.05    -- -100.00 -61.00 -30.00   50
 17  ω   -161.00-114.00   0.50    0.05    -- -100.00 -61.00 -30.00   94
 18  ω   -172.00 -88.00   0.50    0.05    -- -100.00 -30.00-150.00  168
 19  ω   -165.00 -85.00   0.50    0.05    -- -100.00 -45.00-180.00  160
 20  ω   -140.00-115.00   0.50    0.05    -- -100.00-100.00-103.00   50
 21  ω   -151.00 -84.00   0.50    0.05    -- -100.00 -94.00 -60.00  134
 22  ω     71.00 106.00   0.50    0.05    --  104.88 -94.00-180.00   70
 23  ω     76.00 112.00   0.50    0.05    --  104.88-125.00-150.00   72
 24  ω     35.00  89.00   0.50    0.05    --  104.88-125.00 -30.00  108
 25  ω    -12.00  37.00   0.50    0.05    --   45.56-100.00-103.00   98
 26  ω     37.00  83.00   0.50    0.05    --  104.88-100.00-103.00   92
 27  ω     37.00  64.00   0.50    0.05    --  104.88 -94.00-180.00   54
 28  ω     34.00 111.00   0.50    0.05    --  104.88-125.00   0.00  154
 29  ω     69.00  98.00   0.50    0.05    --  104.88 -94.00  30.00   58
 30  ω     32.00 110.00   0.50    0.05    --  104.88-125.00 120.00  156
 31  ω     32.00  90.00   0.50    0.05    --  104.88 -94.00 150.00  116
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1962508000
_diffrn_orient_matrix_UB_12      0.0800700000
_diffrn_orient_matrix_UB_13      0.0852592000
_diffrn_orient_matrix_UB_21      -0.0520482000
_diffrn_orient_matrix_UB_22      0.1640767000
_diffrn_orient_matrix_UB_23      -0.1082010000
_diffrn_orient_matrix_UB_31      -0.1524442000
_diffrn_orient_matrix_UB_32      -0.1188015000
_diffrn_orient_matrix_UB_33      -0.0446487000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1574
_reflns_number_total             1818
_reflns_odcompleteness_completeness 99.35
_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 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       0.008(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1818
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0480
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0974P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1374
_refine_ls_wR_factor_ref         0.1414
_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 Ternary CH refined with riding coordinates:
 C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), 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
F8 F 0.94632(13) 0.65604(12) 0.39840(8) 0.0246(3) Uani 1 1 d . . . . .
F16 F 1.00361(14) 0.51204(12) 0.15710(9) 0.0280(3) Uani 1 1 d . . . . .
O11 O -0.04052(17) 0.91894(15) 0.78641(11) 0.0281(3) Uani 1 1 d . . . . .
O10 O 0.22839(18) 0.83746(16) 0.90172(11) 0.0284(3) Uani 1 1 d . . . . .
N9 N 0.1518(2) 0.85697(17) 0.80124(13) 0.0223(3) Uani 1 1 d . . . . .
C7 C 0.7327(2) 0.7005(2) 0.37238(15) 0.0201(4) Uani 1 1 d . . . . .
C12 C 0.7014(2) 0.71411(19) 0.25294(15) 0.0203(4) Uani 1 1 d . . . . .
C4 C 0.2988(2) 0.80667(19) 0.69202(15) 0.0204(4) Uani 1 1 d . . . . .
C1 C 0.5798(2) 0.73012(19) 0.48369(14) 0.0194(4) Uani 1 1 d . . . . .
C2 C 0.6551(2) 0.69626(19) 0.60153(15) 0.0206(4) Uani 1 1 d . . . . .
H2 H 0.803527 0.645015 0.609856 0.025 Uiso 1 1 calc R U . . .
C5 C 0.2173(2) 0.8344(2) 0.57770(15) 0.0214(4) Uani 1 1 d . . . . .
H5 H 0.066173 0.877892 0.571303 0.026 Uiso 1 1 calc R U . . .
C6 C 0.3571(2) 0.7985(2) 0.47260(15) 0.0207(4) Uani 1 1 d . . . . .
H6 H 0.303313 0.819795 0.393069 0.025 Uiso 1 1 calc R U . . .
C3 C 0.5161(2) 0.7364(2) 0.70694(15) 0.0211(4) Uani 1 1 d . . . . .
H3 H 0.568260 0.716325 0.786849 0.025 Uiso 1 1 calc R U . . .
C15 C 0.8646(2) 0.6820(2) 0.14042(15) 0.0221(4) Uani 1 1 d . . . . .
H15 H 0.949495 0.792956 0.107493 0.026 Uiso 1 1 calc R U . . .
C13 C 0.5096(2) 0.7537(2) 0.17442(15) 0.0233(4) Uani 1 1 d . . . . .
H13A H 0.451056 0.888874 0.156077 0.028 Uiso 1 1 calc R U . . .
H13B H 0.389577 0.673033 0.207111 0.028 Uiso 1 1 calc R U . . .
C14 C 0.6715(3) 0.6851(2) 0.06502(15) 0.0266(4) Uani 1 1 d . . . . .
H14A H 0.648855 0.558897 0.050389 0.032 Uiso 1 1 calc R U . . .
H14B H 0.676633 0.778099 -0.014423 0.032 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
F8 C7 1.3691(16) . ?
F16 C15 1.4001(17) . ?
O11 N9 1.2312(16) . ?
O10 N9 1.2303(18) . ?
N9 C4 1.468(2) . ?
C7 C12 1.328(2) . ?
C7 C1 1.462(2) . ?
C12 C15 1.509(2) . ?
C12 C13 1.520(2) . ?
C4 C5 1.379(2) . ?
C4 C3 1.388(2) . ?
C1 C2 1.395(2) . ?
C1 C6 1.409(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.390(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.381(2) . ?
C6 H6 0.9500 . ?
C3 H3 0.9500 . ?
C15 H15 1.0000 . ?
C15 C14 1.535(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.560(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 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
O11 N9 C4 117.99(13) . . ?
O10 N9 O11 123.79(13) . . ?
O10 N9 C4 118.21(12) . . ?
F8 C7 C1 112.46(13) . . ?
C12 C7 F8 115.81(13) . . ?
C12 C7 C1 131.71(13) . . ?
C7 C12 C15 130.05(14) . . ?
C7 C12 C13 138.03(14) . . ?
C15 C12 C13 91.86(12) . . ?
C5 C4 N9 118.82(13) . . ?
C5 C4 C3 122.35(15) . . ?
C3 C4 N9 118.82(14) . . ?
C2 C1 C7 120.10(13) . . ?
C2 C1 C6 119.37(15) . . ?
C6 C1 C7 120.50(14) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 C1 120.94(13) . . ?
C3 C2 H2 119.5 . . ?
C4 C5 H5 120.3 . . ?
C4 C5 C6 119.44(14) . . ?
C6 C5 H5 120.3 . . ?
C1 C6 H6 120.1 . . ?
C5 C6 C1 119.80(15) . . ?
C5 C6 H6 120.1 . . ?
C4 C3 C2 118.03(15) . . ?
C4 C3 H3 121.0 . . ?
C2 C3 H3 121.0 . . ?
F16 C15 C12 115.06(12) . . ?
F16 C15 H15 111.7 . . ?
F16 C15 C14 115.61(13) . . ?
C12 C15 H15 111.7 . . ?
C12 C15 C14 89.23(11) . . ?
C14 C15 H15 111.7 . . ?
C12 C13 H13A 114.0 . . ?
C12 C13 H13B 114.0 . . ?
C12 C13 C14 87.90(11) . . ?
H13A C13 H13B 111.2 . . ?
C14 C13 H13A 114.0 . . ?
C14 C13 H13B 114.0 . . ?
C15 C14 C13 89.39(12) . . ?
C15 C14 H14A 113.7 . . ?
C15 C14 H14B 113.7 . . ?
C13 C14 H14A 113.7 . . ?
C13 C14 H14B 113.7 . . ?
H14A C14 H14B 111.0 . . ?

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
F8 C7 C12 C15 2.2(2) . . . . ?
F8 C7 C12 C13 178.53(15) . . . . ?
F8 C7 C1 C2 -5.49(18) . . . . ?
F8 C7 C1 C6 172.54(11) . . . . ?
F16 C15 C14 C13 127.12(12) . . . . ?
O11 N9 C4 C5 1.3(2) . . . . ?
O11 N9 C4 C3 -179.93(11) . . . . ?
O10 N9 C4 C5 -177.63(12) . . . . ?
O10 N9 C4 C3 1.12(19) . . . . ?
N9 C4 C5 C6 176.12(12) . . . . ?
N9 C4 C3 C2 -177.61(12) . . . . ?
C7 C12 C15 F16 49.7(2) . . . . ?
C7 C12 C15 C14 167.79(16) . . . . ?
C7 C12 C13 C14 -167.59(18) . . . . ?
C7 C1 C2 C3 175.35(12) . . . . ?
C7 C1 C6 C5 -176.85(13) . . . . ?
C12 C7 C1 C2 176.59(14) . . . . ?
C12 C7 C1 C6 -5.4(2) . . . . ?
C12 C15 C14 C13 9.51(11) . . . . ?
C12 C13 C14 C15 -9.45(11) . . . . ?
C4 C5 C6 C1 1.4(2) . . . . ?
C1 C7 C12 C15 -179.95(13) . . . . ?
C1 C7 C12 C13 -3.6(3) . . . . ?
C1 C2 C3 C4 1.6(2) . . . . ?
C2 C1 C6 C5 1.2(2) . . . . ?
C5 C4 C3 C2 1.1(2) . . . . ?
C6 C1 C2 C3 -2.7(2) . . . . ?
C3 C4 C5 C6 -2.6(2) . . . . ?
C15 C12 C13 C14 9.61(11) . . . . ?
C13 C12 C15 F16 -127.87(13) . . . . ?
C13 C12 C15 C14 -9.77(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.346
_oxdiff_exptl_absorpt_empirical_full_min 0.321
