# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_y
_database_code_depnum_ccdc_archive 'CCDC 2182469'
loop_
_audit_author_name
_audit_author_address
wcy
;ccnu
China
;
_audit_update_record             
;
2022-06-28 deposited with the CCDC.	2023-06-12 downloaded from the CCDC.
;
_audit_creation_date             2022-06-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H6 Cl F3 O'
_chemical_formula_sum            'C9 H6 Cl F3 O'
_chemical_formula_weight         222.59
_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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'

_cell_length_a                   15.120(3)
_cell_length_b                   5.9966(13)
_cell_length_c                   20.980(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1902.3(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6587
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      31.29
_cell_measurement_theta_min      2.36
_shelx_estimated_absorpt_T_max   0.960
_shelx_estimated_absorpt_T_min   0.941
_exptl_absorpt_coefficient_mu    0.409
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.5605
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.1292 before and 0.0663 after correction. The Ratio of minimum to maximum transmission is 0.7510. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            12735
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.991
_diffrn_reflns_theta_min         1.941
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1527
_reflns_number_total             1861
_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       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XM (Sheldrick, 2008)'
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       0.057(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1861
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0534
_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)+(0.0594P)²+1.1406P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1325
_refine_ls_wR_factor_ref         0.1467
_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:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.3, Nqual =  -1, Ralpha = 0.055
;
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 0.63437(13) 0.6052(4) 0.42515(11) 0.0490(5) Uani 1 1 d . . . . .
C2 C 0.59472(15) 0.3979(4) 0.42314(13) 0.0582(6) Uani 1 1 d . . . . .
H2 H 0.5751 0.3414 0.3844 0.070 Uiso 1 1 calc R . . . .
C3 C 0.58394(17) 0.2741(5) 0.47774(14) 0.0664(7) Uani 1 1 d . . . . .
H3 H 0.5571 0.1346 0.4760 0.080 Uiso 1 1 calc R . . . .
C4 C 0.61317(17) 0.3585(5) 0.53478(13) 0.0644(7) Uani 1 1 d . . . . .
C5 C 0.65294(17) 0.5645(5) 0.53873(12) 0.0674(7) Uani 1 1 d . . . . .
H5 H 0.6723 0.6197 0.5778 0.081 Uiso 1 1 calc R . . . .
C6 C 0.66357(15) 0.6876(4) 0.48372(12) 0.0587(6) Uani 1 1 d . . . . .
H6 H 0.6905 0.8269 0.4857 0.070 Uiso 1 1 calc R . . . .
C7 C 0.64894(14) 0.7439(4) 0.36714(12) 0.0534(6) Uani 1 1 d . . . . .
C8 C 0.61765(18) 0.6535(5) 0.30410(12) 0.0658(7) Uani 1 1 d . . . . .
H8A H 0.6512 0.5199 0.2943 0.079 Uiso 1 1 calc R . . . .
H8B H 0.5561 0.6106 0.3082 0.079 Uiso 1 1 calc R . . . .
C9 C 0.6260(2) 0.8119(6) 0.24946(14) 0.0795(8) Uani 1 1 d . . . . .
Cl1 Cl 0.60134(7) 0.19845(18) 0.60321(4) 0.1006(4) Uani 1 1 d . . . . .
F1 F 0.70890(14) 0.8608(4) 0.23556(10) 0.1083(7) Uani 1 1 d . . . . .
F2 F 0.59102(19) 0.7270(5) 0.19654(9) 0.1333(10) Uani 1 1 d . . . . .
F3 F 0.58461(16) 1.0024(4) 0.25895(11) 0.1238(9) Uani 1 1 d . . . . .
O1 O 0.68487(14) 0.9244(3) 0.37013(10) 0.0778(6) Uani 1 1 d . . . . .

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 0.0393(10) 0.0508(12) 0.0569(12) -0.0089(10) -0.0018(9) 0.0036(9)
C2 0.0575(13) 0.0555(13) 0.0616(14) -0.0093(11) 0.0010(10) -0.0026(11)
C3 0.0640(14) 0.0572(14) 0.0779(18) -0.0017(13) 0.0083(12) -0.0027(11)
C4 0.0578(13) 0.0711(17) 0.0642(15) 0.0071(13) 0.0120(11) 0.0186(12)
C5 0.0656(15) 0.0807(18) 0.0558(14) -0.0121(13) -0.0051(11) 0.0152(13)
C6 0.0539(12) 0.0594(14) 0.0628(14) -0.0115(11) -0.0070(10) 0.0027(10)
C7 0.0449(11) 0.0538(12) 0.0615(14) -0.0083(11) -0.0050(9) 0.0012(10)
C8 0.0644(14) 0.0744(17) 0.0587(15) -0.0082(12) 0.0004(11) -0.0118(12)
C9 0.0812(19) 0.093(2) 0.0646(17) -0.0010(15) -0.0038(14) -0.0050(17)
Cl1 0.1128(7) 0.1097(8) 0.0795(6) 0.0282(5) 0.0217(4) 0.0261(5)
F1 0.1016(14) 0.1250(17) 0.0982(14) 0.0158(12) 0.0247(11) -0.0211(13)
F2 0.178(2) 0.166(2) 0.0559(11) -0.0010(12) -0.0185(12) -0.0523(19)
F3 0.142(2) 0.1274(19) 0.1021(15) 0.0153(14) -0.0241(13) 0.0537(16)
O1 0.0938(14) 0.0610(11) 0.0786(12) 0.0004(10) -0.0158(10) -0.0187(10)

_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 1.381(3) . ?
C1 C6 1.396(3) . ?
C1 C7 1.490(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.375(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.372(4) . ?
C4 C5 1.377(4) . ?
C4 Cl1 1.736(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.379(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.506(3) . ?
C7 O1 1.212(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.494(4) . ?
C9 F1 1.319(4) . ?
C9 F2 1.331(4) . ?
C9 F3 1.318(4) . ?

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 118.9(2) . . ?
C2 C1 C7 122.8(2) . . ?
C6 C1 C7 118.3(2) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.8(2) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 120.4 . . ?
C4 C3 C2 119.3(2) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C5 121.6(3) . . ?
C3 C4 Cl1 119.0(2) . . ?
C5 C4 Cl1 119.4(2) . . ?
C4 C5 H5 120.6 . . ?
C4 C5 C6 118.7(2) . . ?
C6 C5 H5 120.6 . . ?
C1 C6 H6 119.7 . . ?
C5 C6 C1 120.7(2) . . ?
C5 C6 H6 119.7 . . ?
C1 C7 C8 118.0(2) . . ?
O1 C7 C1 121.5(2) . . ?
O1 C7 C8 120.5(2) . . ?
C7 C8 H8A 108.6 . . ?
C7 C8 H8B 108.6 . . ?
H8A C8 H8B 107.6 . . ?
C9 C8 C7 114.7(2) . . ?
C9 C8 H8A 108.6 . . ?
C9 C8 H8B 108.6 . . ?
F1 C9 C8 113.0(3) . . ?
F1 C9 F2 106.1(3) . . ?
F2 C9 C8 111.3(3) . . ?
F3 C9 C8 113.3(3) . . ?
F3 C9 F1 107.0(3) . . ?
F3 C9 F2 105.6(3) . . ?

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 -0.1(4) . . . . ?
C1 C7 C8 C9 173.9(2) . . . . ?
C2 C1 C6 C5 -0.1(3) . . . . ?
C2 C1 C7 C8 0.9(3) . . . . ?
C2 C1 C7 O1 -179.1(2) . . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
C2 C3 C4 Cl1 -178.68(18) . . . . ?
C3 C4 C5 C6 -0.2(4) . . . . ?
C4 C5 C6 C1 0.2(4) . . . . ?
C6 C1 C2 C3 0.1(3) . . . . ?
C6 C1 C7 C8 179.7(2) . . . . ?
C6 C1 C7 O1 -0.3(3) . . . . ?
C7 C1 C2 C3 178.9(2) . . . . ?
C7 C1 C6 C5 -179.0(2) . . . . ?
C7 C8 C9 F1 65.4(3) . . . . ?
C7 C8 C9 F2 -175.3(3) . . . . ?
C7 C8 C9 F3 -56.5(4) . . . . ?
Cl1 C4 C5 C6 178.61(18) . . . . ?
O1 C7 C8 C9 -6.1(4) . . . . ?

_iucr_refine_instructions_details 
;

    y.res created by SHELXL-2014/7

TITL y in Pbca
CELL 0.71073 15.1203 5.9966 20.9802 90 90 90
ZERR 8 0.0032 0.0013 0.0043 0 0 0
LATT 1
SYMM 0.5+X,0.5-Y,-Z
SYMM -X,0.5+Y,0.5-Z
SYMM 0.5-X,-Y,0.5+Z
SFAC C H Cl F O
UNIT 72 48 8 24 8
 
L.S. 20
PLAN  -11 0 0
SIZE 0.15 0.12 0.1
TEMP 23
BOND $H
HTAB
CONF
fmap 2
acta
OMIT -3 52
OMIT 0 0 16
OMIT 2 0 18
REM <olex2.extras>
REM <HklSrc "%.\\y.hkl">
REM </olex2.extras>
 
WGHT    0.059400    1.140600
EXTI    0.057212
FVAR       0.20794
C1    1    0.634368    0.605233    0.425153    11.00000    0.03932    0.05079 =
         0.05694   -0.00888   -0.00175    0.00364
C2    1    0.594723    0.397950    0.423138    11.00000    0.05754    0.05552 =
         0.06159   -0.00934    0.00099   -0.00262
AFIX  43
H2    2    0.575068    0.341397    0.384369    11.00000   -1.20000
AFIX   0
C3    1    0.583941    0.274098    0.477739    11.00000    0.06402    0.05723 =
         0.07788   -0.00175    0.00834   -0.00272
AFIX  43
H3    2    0.557129    0.134648    0.476034    11.00000   -1.20000
AFIX   0
C4    1    0.613166    0.358458    0.534784    11.00000    0.05776    0.07109 =
         0.06423    0.00711    0.01204    0.01862
C5    1    0.652937    0.564520    0.538735    11.00000    0.06559    0.08073 =
         0.05580   -0.01209   -0.00513    0.01517
AFIX  43
H5    2    0.672266    0.619688    0.577751    11.00000   -1.20000
AFIX   0
C6    1    0.663572    0.687599    0.483719    11.00000    0.05387    0.05936 =
         0.06278   -0.01152   -0.00702    0.00269
AFIX  43
H6    2    0.690476    0.826896    0.485666    11.00000   -1.20000
AFIX   0
C7    1    0.648944    0.743906    0.367139    11.00000    0.04489    0.05377 =
         0.06154   -0.00833   -0.00505    0.00121
C8    1    0.617647    0.653511    0.304100    11.00000    0.06440    0.07441 =
         0.05872   -0.00818    0.00040   -0.01185
AFIX  23
H8A   2    0.651182    0.519918    0.294329    11.00000   -1.20000
H8B   2    0.556061    0.610597    0.308235    11.00000   -1.20000
AFIX   0
C9    1    0.626024    0.811941    0.249462    11.00000    0.08124    0.09272 =
         0.06458   -0.00102   -0.00375   -0.00498
CL1   3    0.601339    0.198454    0.603208    11.00000    0.11278    0.10967 =
         0.07947    0.02825    0.02166    0.02613
F1    4    0.708899    0.860767    0.235565    11.00000    0.10159    0.12503 =
         0.09821    0.01579    0.02471   -0.02112
F2    4    0.591025    0.727031    0.196545    11.00000    0.17806    0.16599 =
         0.05591   -0.00097   -0.01851   -0.05230
F3    4    0.584615    1.002385    0.258946    11.00000    0.14180    0.12744 =
         0.10208    0.01527   -0.02413    0.05373
O1    5    0.684873    0.924357    0.370133    11.00000    0.09383    0.06095 =
         0.07863    0.00043   -0.01577   -0.01874
HKLF 4
 
REM  y in Pbca
REM R1 =  0.0534 for    1527 Fo > 4sig(Fo)  and  0.0638 for all    1861 data
REM    128 parameters refined using      0 restraints
 
END  
     
WGHT      0.0590      1.1434 

REM Instructions for potential hydrogen bonds
EQIV $1 -x+3/2, y-1/2, z
HTAB C8 F1_$1
EQIV $2 -x+1, y-1/2, -z+1/2
HTAB C8 F3_$2

REM Highest difference peak  0.325,  deepest hole -0.242,  1-sigma level  0.073
Q1    1   0.6756  0.9896  0.2517  11.00000  0.05    0.32
Q2    1   0.5375  0.8781  0.2563  11.00000  0.05    0.22
Q3    1   0.6601  0.6680  0.1938  11.00000  0.05    0.22
Q4    1   0.5224  0.5929  0.2128  11.00000  0.05    0.19
Q5    1   0.7185  0.8270  0.3496  11.00000  0.05    0.18
Q6    1   0.5830  0.5330  0.4256  11.00000  0.05    0.18
Q7    1   0.5539 -0.0008  0.5900  11.00000  0.05    0.18
Q8    1   0.7337  0.5192  0.5611  11.00000  0.05    0.18
Q9    1   0.5258  1.0249  0.2878  11.00000  0.05    0.18
Q10   1   0.4845  0.9098  0.2482  11.00000  0.05    0.18
Q11   1   0.7555  0.0324  0.4315  11.00000  0.05    0.16

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0534 for 1527 Fo > 4sig(Fo) and 0.0638 for all 19801 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 0.32, deepest hole -0.24
  REM Mean Shift 0, Max Shift 0.000.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.0638
  REM R1_gt = 0.0534
  REM wR_ref = 0.1467
  REM GOOF = 1.067
  REM Shift_max = 0.000
  REM Shift_mean = 0
  REM Reflections_all = 19801
  REM Reflections_gt = 1527
  REM Parameters = n/a
  REM Hole = -0.24
  REM Peak = 0.32
  REM Flack = n/a

  
;
_olex2_submission_special_instructions 'No special instructions were received'
