# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_t
_database_code_depnum_ccdc_archive 'CCDC 1885342'
loop_
_audit_author_name
_audit_author_address
'Jia-Rong Chen'
;Central China Normal University
China
;
_audit_update_record             
;
2018-12-16 deposited with the CCDC.	2019-02-18 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H12 Cl F3 O2'
_chemical_formula_sum            'C17 H12 Cl F3 O2'
_chemical_formula_weight         340.72
_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'
O O 0.0106 0.0060 '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'

_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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.402(11)
_cell_length_b                   11.908(16)
_cell_length_c                   17.31(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.68(2)
_cell_angle_gamma                90
_cell_volume                     1521(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3588
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.0768
_cell_measurement_theta_min      2.3604
_shelx_estimated_absorpt_T_max   0.972
_shelx_estimated_absorpt_T_min   0.955
_exptl_absorpt_coefficient_mu    0.289
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10621
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.496
_diffrn_reflns_theta_min         2.078
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'omega sacan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2198
_reflns_number_total             2826
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    ?
_computing_publication_material  ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    ?
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.485
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2826
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0483
_refine_ls_restrained_S_all      1.033
_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)+(0.0888P)²+0.5376P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1408
_refine_ls_wR_factor_ref         0.1572
_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:
 C8(H8), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C12(H12), C5(H5), C13(H13), C14(H14), C3(H3), C2(H2), C15(H15)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
Cl1 Cl 0.24191(12) -0.05377(7) -0.11985(6) 0.0892(3) Uani 1 1 d . . . . .
C6 C 0.0860(3) 0.2198(2) -0.01692(14) 0.0521(6) Uani 1 1 d . . . . .
H6 H 0.019279 0.283874 -0.030745 0.062 Uiso 1 1 calc R . . . .
O3 O 0.1893(2) 0.44812(13) 0.04031(9) 0.0507(4) Uani 1 1 d . . . . .
C12 C 0.3789(3) 0.6109(2) 0.03091(15) 0.0523(6) Uani 1 1 d . . . . .
H12 H 0.416785 0.589671 -0.016868 0.063 Uiso 1 1 calc R . . . .
F3 F -0.4019(2) 0.50749(19) 0.21876(12) 0.0956(7) Uani 1 1 d . . . . .
O6 O 0.1549(4) 0.26645(17) 0.18747(11) 0.0865(7) Uani 1 1 d . . . . .
F2 F -0.1769(2) 0.43113(16) 0.27881(9) 0.0754(5) Uani 1 1 d . . . . .
C4 C 0.2067(3) 0.0464(2) -0.05054(17) 0.0576(6) Uani 1 1 d . . . . .
C5 C 0.1112(3) 0.1404(2) -0.07184(16) 0.0578(6) Uani 1 1 d . . . . .
H5 H 0.064110 0.150494 -0.122821 0.069 Uiso 1 1 calc R . . . .
C13 C 0.4393(3) 0.7076(2) 0.06716(18) 0.0623(7) Uani 1 1 d . . . . .
H13 H 0.520910 0.753141 0.043698 0.075 Uiso 1 1 calc R . . . .
C17 C -0.2420(3) 0.4635(2) 0.20907(15) 0.0574(6) Uani 1 1 d . . . . .
C14 C 0.3819(4) 0.7384(2) 0.13710(18) 0.0666(7) Uani 1 1 d . . . . .
H14 H 0.426289 0.804050 0.160820 0.080 Uiso 1 1 calc R . . . .
C3 C 0.2772(4) 0.0302(2) 0.02332(17) 0.0641(7) Uani 1 1 d . . . . .
H3 H 0.341385 -0.035021 0.036620 0.077 Uiso 1 1 calc R . . . .
C2 C 0.2536(4) 0.1104(2) 0.07824(16) 0.0576(6) Uani 1 1 d . . . . .
H2 H 0.302627 0.099709 0.128882 0.069 Uiso 1 1 calc R . . . .
F1 F -0.2724(3) 0.36924(17) 0.16907(11) 0.0877(6) Uani 1 1 d . . . . .
C1 C 0.1574(3) 0.20692(19) 0.05880(13) 0.0464(5) Uani 1 1 d . . . . .
C7 C 0.1311(3) 0.2899(2) 0.12001(13) 0.0505(6) Uani 1 1 d . . . . .
C8 C 0.0679(3) 0.40649(18) 0.09553(12) 0.0439(5) Uani 1 1 d . . . . .
H8 H -0.054641 0.401180 0.069739 0.053 Uiso 1 1 calc R . . . .
C11 C 0.2597(3) 0.54691(18) 0.06856(13) 0.0449(5) Uani 1 1 d . . . . .
C16 C -0.1195(3) 0.5408(2) 0.17267(14) 0.0507(6) Uani 1 1 d . . . . .
H16A H -0.103849 0.607816 0.204352 0.061 Uiso 1 1 calc R . . . .
H16B H -0.175687 0.563192 0.122459 0.061 Uiso 1 1 calc R . . . .
C9 C 0.0664(3) 0.49115(19) 0.16181(12) 0.0449(5) Uani 1 1 d . . . . .
H9 H 0.114736 0.455596 0.210206 0.054 Uiso 1 1 calc R . . . .
C10 C 0.1973(3) 0.57710(19) 0.13805(13) 0.0451(5) Uani 1 1 d . . . . .
C15 C 0.2594(3) 0.6737(2) 0.17291(15) 0.0570(6) Uani 1 1 d . . . . .
H15 H 0.219652 0.695616 0.220211 0.068 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
Cl1 C4 1.727(3) . ?
C6 H6 0.9300 . ?
C6 C5 1.364(4) . ?
C6 C1 1.382(4) . ?
O3 C8 1.452(3) . ?
O3 C11 1.361(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.369(4) . ?
C12 C11 1.370(4) . ?
F3 C17 1.317(3) . ?
O6 C7 1.200(3) . ?
F2 C17 1.321(3) . ?
C4 C5 1.359(4) . ?
C4 C3 1.355(4) . ?
C5 H5 0.9300 . ?
C13 H13 0.9300 . ?
C13 C14 1.366(4) . ?
C17 F1 1.329(4) . ?
C17 C16 1.470(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.376(4) . ?
C3 H3 0.9300 . ?
C3 C2 1.368(4) . ?
C2 H2 0.9300 . ?
C2 C1 1.379(4) . ?
C1 C7 1.473(4) . ?
C7 C8 1.515(4) . ?
C8 H8 0.9800 . ?
C8 C9 1.528(3) . ?
C11 C10 1.372(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C9 1.523(4) . ?
C9 H9 0.9800 . ?
C9 C10 1.490(4) . ?
C10 C15 1.362(4) . ?
C15 H15 0.9300 . ?

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
C5 C6 H6 119.3 . . ?
C5 C6 C1 121.4(2) . . ?
C1 C6 H6 119.3 . . ?
C11 O3 C8 107.33(18) . . ?
C13 C12 H12 121.7 . . ?
C13 C12 C11 116.6(2) . . ?
C11 C12 H12 121.7 . . ?
C5 C4 Cl1 119.0(2) . . ?
C3 C4 Cl1 119.3(2) . . ?
C3 C4 C5 121.7(2) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 C6 118.6(3) . . ?
C4 C5 H5 120.7 . . ?
C12 C13 H13 119.4 . . ?
C14 C13 C12 121.3(2) . . ?
C14 C13 H13 119.4 . . ?
F3 C17 F2 105.3(2) . . ?
F3 C17 F1 106.7(2) . . ?
F3 C17 C16 113.4(2) . . ?
F2 C17 F1 105.3(2) . . ?
F2 C17 C16 112.5(2) . . ?
F1 C17 C16 112.9(2) . . ?
C13 C14 H14 119.6 . . ?
C13 C14 C15 120.8(3) . . ?
C15 C14 H14 119.6 . . ?
C4 C3 H3 120.1 . . ?
C4 C3 C2 119.7(3) . . ?
C2 C3 H3 120.1 . . ?
C3 C2 H2 119.9 . . ?
C3 C2 C1 120.3(3) . . ?
C1 C2 H2 119.9 . . ?
C6 C1 C7 123.1(2) . . ?
C2 C1 C6 118.3(2) . . ?
C2 C1 C7 118.6(2) . . ?
O6 C7 C1 121.8(2) . . ?
O6 C7 C8 120.2(2) . . ?
C1 C7 C8 118.0(2) . . ?
O3 C8 C7 107.69(18) . . ?
O3 C8 H8 108.8 . . ?
O3 C8 C9 108.19(19) . . ?
C7 C8 H8 108.8 . . ?
C7 C8 C9 114.56(19) . . ?
C9 C8 H8 108.8 . . ?
O3 C11 C12 123.5(2) . . ?
O3 C11 C10 113.3(2) . . ?
C12 C11 C10 123.2(2) . . ?
C17 C16 H16A 108.8 . . ?
C17 C16 H16B 108.8 . . ?
C17 C16 C9 113.9(2) . . ?
H16A C16 H16B 107.7 . . ?
C9 C16 H16A 108.8 . . ?
C9 C16 H16B 108.8 . . ?
C8 C9 H9 109.4 . . ?
C16 C9 C8 114.2(2) . . ?
C16 C9 H9 109.4 . . ?
C10 C9 C8 101.60(19) . . ?
C10 C9 C16 112.4(2) . . ?
C10 C9 H9 109.4 . . ?
C11 C10 C9 109.6(2) . . ?
C15 C10 C11 119.0(2) . . ?
C15 C10 C9 131.4(2) . . ?
C14 C15 H15 120.5 . . ?
C10 C15 C14 119.0(2) . . ?
C10 C15 H15 120.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C5 H5 F2 0.93 2.56 3.326(4) 140.4 4_565 yes

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
Cl1 C4 C5 C6 -179.2(2) . . . . ?
Cl1 C4 C3 C2 178.5(2) . . . . ?
C6 C1 C7 O6 161.8(3) . . . . ?
C6 C1 C7 C8 -16.7(3) . . . . ?
O3 C8 C9 C16 120.1(2) . . . . ?
O3 C8 C9 C10 -1.2(2) . . . . ?
O3 C11 C10 C9 -0.6(3) . . . . ?
O3 C11 C10 C15 179.2(2) . . . . ?
C12 C13 C14 C15 -0.8(4) . . . . ?
C12 C11 C10 C9 178.4(2) . . . . ?
C12 C11 C10 C15 -1.8(3) . . . . ?
F3 C17 C16 C9 179.5(2) . . . . ?
O6 C7 C8 O3 129.0(3) . . . . ?
O6 C7 C8 C9 8.6(3) . . . . ?
F2 C17 C16 C9 60.1(3) . . . . ?
C4 C3 C2 C1 0.5(4) . . . . ?
C5 C6 C1 C2 -0.9(4) . . . . ?
C5 C6 C1 C7 -179.1(2) . . . . ?
C5 C4 C3 C2 -0.4(4) . . . . ?
C13 C12 C11 O3 -179.3(2) . . . . ?
C13 C12 C11 C10 1.8(3) . . . . ?
C13 C14 C15 C10 0.8(4) . . . . ?
C17 C16 C9 C8 75.1(3) . . . . ?
C17 C16 C9 C10 -169.8(2) . . . . ?
C3 C4 C5 C6 -0.3(4) . . . . ?
C3 C2 C1 C6 0.2(4) . . . . ?
C3 C2 C1 C7 178.5(2) . . . . ?
C2 C1 C7 O6 -16.4(4) . . . . ?
C2 C1 C7 C8 165.1(2) . . . . ?
F1 C17 C16 C9 -59.0(3) . . . . ?
C1 C6 C5 C4 1.0(4) . . . . ?
C1 C7 C8 O3 -52.5(3) . . . . ?
C1 C7 C8 C9 -172.9(2) . . . . ?
C7 C8 C9 C16 -119.8(2) . . . . ?
C7 C8 C9 C10 118.9(2) . . . . ?
C8 O3 C11 C12 -179.2(2) . . . . ?
C8 O3 C11 C10 -0.2(2) . . . . ?
C8 C9 C10 C11 1.1(2) . . . . ?
C8 C9 C10 C15 -178.7(2) . . . . ?
C11 O3 C8 C7 -123.4(2) . . . . ?
C11 O3 C8 C9 0.9(2) . . . . ?
C11 C12 C13 C14 -0.4(4) . . . . ?
C11 C10 C15 C14 0.4(4) . . . . ?
C16 C9 C10 C11 -121.5(2) . . . . ?
C16 C9 C10 C15 58.8(3) . . . . ?
C9 C10 C15 C14 -179.8(2) . . . . ?

