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

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

data_exp_3268_auto
_database_code_depnum_ccdc_archive 'CCDC 2177415'
loop_
_audit_author_name
_audit_author_address
'Shuwen Zhao'
;Wuyi University
China
;
_audit_update_record             
;
2022-06-07 deposited with the CCDC.	2022-07-12 downloaded from the CCDC.
;
_audit_creation_date             2022-05-21
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H6 Cl F3 O3'
_chemical_formula_sum            'C11 H6 Cl F3 O3'
_chemical_formula_weight         278.61
_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'
Cl Cl 0.3639 0.7018 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   4.72550(10)
_cell_length_b                   22.4433(7)
_cell_length_c                   10.8444(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.625(3)
_cell_angle_gamma                90
_cell_volume                     1146.37(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4377
_cell_measurement_temperature    297.56(10)
_cell_measurement_theta_max      75.1880
_cell_measurement_theta_min      3.9350
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.363
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51873
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.614
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             560
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7225
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.402
_diffrn_reflns_theta_min         3.939
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297.56(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     94.00 167.00   0.50    0.88    --  108.86  57.00 -90.00  146
  2  ω    145.00 177.00   0.50    0.88    --  108.86 125.00-150.00   64
  3  ω     96.00 123.00   0.50    0.88    --  108.86 125.00-150.00   54
  4  ω    105.00 130.00   0.50    0.88    --  108.86 140.00  -9.00   50
  5  ω    -62.00 -37.00   0.50    0.88    --  -91.75 140.00  -9.00   50
  6  ω    -73.00 -25.00   0.50    0.22    --  -48.55 140.00  -9.00   96
  7  ω   -115.00 -27.00   0.50    0.22    --  -48.55 -77.00   0.00  176
  8  ω   -163.00 -77.00   0.50    0.88    --  -91.75-130.00 104.00  172
  9  ω   -120.00 -95.00   0.50    0.22    --  -48.55-130.00 104.00   50
 10  ω   -116.00 -91.00   0.50    0.22    --  -48.55-140.00 -69.00   50
 11  ω   -163.00 -91.00   0.50    0.88    --  -91.75 -57.00 -60.00  144
 12  ω    -24.00  24.00   0.50    0.22    --  -48.55  19.00 -60.00   96
 13  ω    -45.00 -20.00   0.50    0.88    --  -91.75  57.00-150.00   50
 14  ω   -104.00 -75.00   0.50    0.88    --  -91.75  77.00   0.00   58
 15  ω    -61.00 -20.00   0.50    0.88    --  -91.75  57.00 -30.00   82
 16  ω    -53.00 -22.00   0.50    0.88    --  -91.75  57.00   0.00   62
 17  ω     38.00  66.00   0.50    0.88    --  108.86 -57.00  60.00   56
 18  ω     63.00  95.00   0.50    0.88    --  108.86 -77.00  90.00   64
 19  ω     40.00  65.00   0.50    0.88    --  108.86 -57.00 150.00   50
 20  ω     47.00  75.00   0.50    0.88    --  108.86-130.00 104.00   56
 21  ω     89.00 114.00   0.50    0.88    --  108.86-130.00 104.00   50
 22  ω     57.00  82.00   0.50    0.22    --   48.55-130.00 104.00   50
 23  ω     57.00 104.00   0.50    0.22    --   48.55-140.00 -69.00   94
 24  ω     94.00 119.00   0.50    0.88    --  108.86-140.00 -69.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0137765000
_diffrn_orient_matrix_UB_12      -0.0524852000
_diffrn_orient_matrix_UB_13      -0.0918128000
_diffrn_orient_matrix_UB_21      0.0003276000
_diffrn_orient_matrix_UB_22      0.0441668000
_diffrn_orient_matrix_UB_23      -0.1087404000
_diffrn_orient_matrix_UB_31      0.3268239000
_diffrn_orient_matrix_UB_32      -0.0022551000
_diffrn_orient_matrix_UB_33      0.0076990000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1861
_reflns_number_total             2253
_reflns_odcompleteness_completeness 99.95
_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 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (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         0.625
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         2253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0740
_refine_ls_R_factor_gt           0.0654
_refine_ls_restrained_S_all      1.096
_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)+(0.0996P)²+0.4930P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1875
_refine_ls_wR_factor_ref         0.1968
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
: with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Others
 Fixed Sof: F15B(0.5) F15A(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C8(H8), C7(H7)
;
_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
Cl18 Cl 0.8917(2) 0.23215(5) 0.60094(10) 0.1014(4) Uani 1 1 d . . . . .
O10 O 0.5781(4) 0.42459(9) 0.25401(17) 0.0654(5) Uani 1 1 d . . . . .
O11 O 0.3674(4) 0.50458(10) 0.18868(18) 0.0716(6) Uani 1 1 d . . . . .
O17 O 0.2058(5) 0.42262(10) 0.57997(19) 0.0729(6) Uani 1 1 d . . . . .
F16 F 0.0950(6) 0.64624(13) 0.1099(3) 0.1250(10) Uani 1 1 d . . . . .
C4 C 0.5196(5) 0.37700(12) 0.4494(2) 0.0541(6) Uani 1 1 d . . . . .
F14 F 0.1368(9) 0.57343(19) -0.0093(3) 0.1644(15) Uani 1 1 d . . . . .
C1 C 0.3892(5) 0.46632(13) 0.2823(2) 0.0575(6) Uani 1 1 d . . . . .
C3 C 0.3137(6) 0.42307(12) 0.4804(2) 0.0566(6) Uani 1 1 d . . . . .
C9 C 0.6418(5) 0.37961(12) 0.3378(2) 0.0571(6) Uani 1 1 d . . . . .
C2 C 0.2543(6) 0.46736(12) 0.3863(2) 0.0574(6) Uani 1 1 d . . . . .
H2 H 0.121181 0.496974 0.397625 0.069 Uiso 1 1 calc R U . . .
C5 C 0.5952(6) 0.33033(13) 0.5304(3) 0.0625(7) Uani 1 1 d . . . . .
H5 H 0.514448 0.327326 0.605534 0.075 Uiso 1 1 calc R U . . .
C8 C 0.8355(6) 0.33748(14) 0.3050(3) 0.0673(7) Uani 1 1 d . . . . .
H8 H 0.914357 0.339942 0.229306 0.081 Uiso 1 1 calc R U . . .
C6 C 0.7893(6) 0.28900(14) 0.4983(3) 0.0676(7) Uani 1 1 d . . . . .
F15B F 0.4848(9) 0.5981(2) 0.0601(4) 0.0909(11) Uiso 0.5 1 d . . P A 2
C7 C 0.9097(6) 0.29189(15) 0.3858(3) 0.0712(8) Uani 1 1 d . . . . .
H7 H 1.039822 0.263167 0.365344 0.085 Uiso 1 1 calc R U . . .
C12 C 0.1869(7) 0.55488(15) 0.2015(3) 0.0713(8) Uani 1 1 d . . . . .
H12A H 0.234383 0.574618 0.279988 0.086 Uiso 1 1 calc R U . . .
H12B H -0.010240 0.542464 0.197973 0.086 Uiso 1 1 calc R U . . .
C13 C 0.2333(8) 0.5955(2) 0.0978(4) 0.0914(12) Uani 1 1 d . . . . .
F15A F 0.5093(10) 0.6199(2) 0.1244(5) 0.1036(13) Uiso 0.5 1 d . . P A 1


_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
Cl18 C6 1.736(3) . ?
O10 C1 1.346(3) . ?
O10 C9 1.376(3) . ?
O11 C1 1.328(3) . ?
O11 C12 1.428(4) . ?
O17 C3 1.231(3) . ?
F16 C13 1.326(5) . ?
C4 C3 1.477(4) . ?
C4 C9 1.383(4) . ?
C4 C5 1.395(4) . ?
F14 C13 1.310(6) . ?
C1 C2 1.340(4) . ?
C3 C2 1.436(4) . ?
C9 C8 1.382(4) . ?
C2 H2 0.9300 . ?
C5 H5 0.9300 . ?
C5 C6 1.369(4) . ?
C8 H8 0.9300 . ?
C8 C7 1.374(5) . ?
C6 C7 1.388(5) . ?
F15B C13 1.289(6) . ?
C7 H7 0.9300 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.477(5) . ?
C13 F15A 1.423(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O10 C9 118.3(2) . . ?
C1 O11 C12 116.6(2) . . ?
C9 C4 C3 119.9(2) . . ?
C9 C4 C5 118.6(2) . . ?
C5 C4 C3 121.5(2) . . ?
O11 C1 O10 106.7(2) . . ?
O11 C1 C2 128.3(3) . . ?
C2 C1 O10 125.0(2) . . ?
O17 C3 C4 121.4(2) . . ?
O17 C3 C2 123.9(3) . . ?
C2 C3 C4 114.7(2) . . ?
O10 C9 C4 121.6(2) . . ?
O10 C9 C8 116.5(2) . . ?
C8 C9 C4 121.9(3) . . ?
C1 C2 C3 120.5(3) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C4 C5 H5 120.3 . . ?
C6 C5 C4 119.4(3) . . ?
C6 C5 H5 120.3 . . ?
C9 C8 H8 120.5 . . ?
C7 C8 C9 119.0(3) . . ?
C7 C8 H8 120.5 . . ?
C5 C6 Cl18 119.5(2) . . ?
C5 C6 C7 121.5(3) . . ?
C7 C6 Cl18 119.0(2) . . ?
C8 C7 C6 119.6(3) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
O11 C12 H12A 110.4 . . ?
O11 C12 H12B 110.4 . . ?
O11 C12 C13 106.7(3) . . ?
H12A C12 H12B 108.6 . . ?
C13 C12 H12A 110.4 . . ?
C13 C12 H12B 110.4 . . ?
F16 C13 C12 110.5(3) . . ?
F16 C13 F15A 95.7(4) . . ?
F14 C13 F16 105.8(3) . . ?
F14 C13 C12 112.3(4) . . ?
F14 C13 F15A 125.0(4) . . ?
F15B C13 F16 117.8(4) . . ?
F15B C13 F14 90.0(4) . . ?
F15B C13 C12 117.9(3) . . ?
F15A C13 C12 105.9(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl18 C6 C7 C8 -178.5(2) . . . . ?
O10 C1 C2 C3 2.4(4) . . . . ?
O10 C9 C8 C7 179.2(2) . . . . ?
O11 C1 C2 C3 -177.5(3) . . . . ?
O11 C12 C13 F16 -173.6(3) . . . . ?
O11 C12 C13 F14 68.5(4) . . . . ?
O11 C12 C13 F15B -34.0(6) . . . . ?
O11 C12 C13 F15A -71.1(4) . . . . ?
O17 C3 C2 C1 177.1(3) . . . . ?
C4 C3 C2 C1 -2.5(4) . . . . ?
C4 C9 C8 C7 -0.4(4) . . . . ?
C4 C5 C6 Cl18 178.1(2) . . . . ?
C4 C5 C6 C7 -1.0(4) . . . . ?
C1 O10 C9 C4 -0.7(4) . . . . ?
C1 O10 C9 C8 179.7(2) . . . . ?
C1 O11 C12 C13 170.7(3) . . . . ?
C3 C4 C9 O10 0.4(4) . . . . ?
C3 C4 C9 C8 180.0(2) . . . . ?
C3 C4 C5 C6 -179.3(3) . . . . ?
C9 O10 C1 O11 179.2(2) . . . . ?
C9 O10 C1 C2 -0.7(4) . . . . ?
C9 C4 C3 O17 -178.5(3) . . . . ?
C9 C4 C3 C2 1.2(4) . . . . ?
C9 C4 C5 C6 0.7(4) . . . . ?
C9 C8 C7 C6 0.1(4) . . . . ?
C5 C4 C3 O17 1.5(4) . . . . ?
C5 C4 C3 C2 -178.8(2) . . . . ?
C5 C4 C9 O10 -179.6(2) . . . . ?
C5 C4 C9 C8 0.0(4) . . . . ?
C5 C6 C7 C8 0.6(5) . . . . ?
C12 O11 C1 O10 -177.0(2) . . . . ?
C12 O11 C1 C2 3.0(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.627
_oxdiff_exptl_absorpt_empirical_full_min 0.545
