# 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_1569_auto
_database_code_depnum_ccdc_archive 'CCDC 2158109'
loop_
_audit_author_name
_audit_author_address
'Xiaodong Xiong'
;Nanchang university
China
;
_audit_update_record             
;
2022-03-12 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H11 Cl F N O2'
_chemical_formula_weight         279.69

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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P c'
_space_group_name_Hall           'P -2yc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'

_cell_length_a                   4.7305(2)
_cell_length_b                   11.4393(4)
_cell_length_c                   12.2488(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.234(3)
_cell_angle_gamma                90
_cell_volume                     661.02(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_F_000             288
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    2.658
_shelx_estimated_absorpt_T_min   0.857
_shelx_estimated_absorpt_T_max   0.901
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4639
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.864
_diffrn_reflns_theta_max         68.061
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.915
_diffrn_reflns_point_group_measured_fraction_full 0.921
_reflns_number_total             2209
_reflns_number_gt                2114
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.836
_reflns_Friedel_fraction_max     0.838
_reflns_Friedel_fraction_full    0.845

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0891P)²+0.0039P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 903 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.012(15)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2209
_refine_ls_number_parameters     172
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1291
_refine_ls_wR_factor_gt          0.1274
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_restrained_S_all      1.104
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.88573(19) 0.46968(8) 0.64384(10) 0.0680(3) Uani 1 1 d . . . . .
F1 F 0.1137(8) 0.7078(4) 0.9156(3) 0.1027(11) Uani 1 1 d . . . . .
O1 O 0.1270(7) 0.7472(4) 0.5291(4) 0.0927(14) Uani 1 1 d . . . . .
O2 O 0.4891(6) 0.7773(3) 0.4239(2) 0.0602(7) Uani 1 1 d . . . . .
N1 N 0.5734(6) 0.6888(3) 0.5820(3) 0.0502(7) Uani 1 1 d . . . . .
H1 H 0.742465 0.684321 0.560933 0.060 Uiso 1 1 calc R U . . .
C1 C 0.6106(12) 0.4985(5) 0.8267(4) 0.0745(12) Uani 1 1 d . . . . .
H1A H 0.705315 0.431309 0.851765 0.089 Uiso 1 1 calc R U . . .
C2 C 0.4237(12) 0.5528(6) 0.8913(4) 0.0790(14) Uani 1 1 d . . . . .
H2 H 0.387041 0.522502 0.959304 0.095 Uiso 1 1 calc R U . . .
C3 C 0.2955(10) 0.6516(5) 0.8526(4) 0.0715(12) Uani 1 1 d . . . . .
C4 C 0.3420(9) 0.7004(4) 0.7521(4) 0.0595(9) Uani 1 1 d . . . . .
H4 H 0.253836 0.769924 0.729583 0.071 Uiso 1 1 calc R U . . .
C5 C 0.5223(7) 0.6435(3) 0.6860(3) 0.0481(7) Uani 1 1 d . . . . .
C6 C 0.6586(9) 0.5434(3) 0.7242(3) 0.0533(8) Uani 1 1 d . . . . .
C7 C 0.3704(8) 0.7387(4) 0.5139(4) 0.0541(8) Uani 1 1 d . . . . .
C8 C 0.2873(11) 0.8274(6) 0.3413(5) 0.0910(19) Uani 1 1 d . . . . .
H8A H 0.175956 0.888152 0.372937 0.109 Uiso 1 1 calc R U . . .
H8B H 0.159851 0.767669 0.310251 0.109 Uiso 1 1 calc R U . . .
C9 C 0.4618(8) 0.8772(4) 0.2554(4) 0.0584(9) Uani 1 1 d . . . . .
C10 C 0.5846(13) 0.9855(5) 0.2673(5) 0.0796(14) Uani 1 1 d . . . . .
H10 H 0.558743 1.029765 0.329499 0.096 Uiso 1 1 calc R U . . .
C11 C 0.7461(16) 1.0289(5) 0.1876(7) 0.101(2) Uani 1 1 d . . . . .
H11 H 0.831579 1.101834 0.196446 0.122 Uiso 1 1 calc R U . . .
C12 C 0.7805(16) 0.9654(9) 0.0962(7) 0.113(3) Uani 1 1 d . . . . .
H12 H 0.887516 0.995488 0.041984 0.136 Uiso 1 1 calc R U . . .
C13 C 0.6605(19) 0.8591(7) 0.0833(6) 0.109(2) Uani 1 1 d . . . . .
H13 H 0.686953 0.815319 0.020875 0.130 Uiso 1 1 calc R U . . .
C14 C 0.5002(13) 0.8157(5) 0.1621(5) 0.0822(15) Uani 1 1 d . . . . .
H14 H 0.415369 0.742810 0.152094 0.099 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
Cl1 C6 1.729(5) . ?
F1 C3 1.358(6) . ?
O1 C7 1.184(5) . ?
O2 C7 1.349(5) . ?
O2 C8 1.456(6) . ?
N1 C7 1.351(5) . ?
N1 C5 1.412(5) . ?
N1 H1 0.8600 . ?
C1 C2 1.378(9) . ?
C1 C6 1.391(6) . ?
C1 H1A 0.9300 . ?
C2 C3 1.352(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.384(7) . ?
C4 C5 1.382(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.379(5) . ?
C8 C9 1.497(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C14 1.365(8) . ?
C9 C10 1.371(8) . ?
C10 C11 1.376(11) . ?
C10 H10 0.9300 . ?
C11 C12 1.354(12) . ?
C11 H11 0.9300 . ?
C12 C13 1.347(12) . ?
C12 H12 0.9300 . ?
C13 C14 1.364(10) . ?
C13 H13 0.9300 . ?
C14 H14 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
C7 O2 C8 113.9(3) . . ?
C7 N1 C5 123.4(3) . . ?
C7 N1 H1 118.3 . . ?
C5 N1 H1 118.3 . . ?
C2 C1 C6 120.4(5) . . ?
C2 C1 H1A 119.8 . . ?
C6 C1 H1A 119.8 . . ?
C3 C2 C1 117.8(4) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C2 C3 F1 118.9(5) . . ?
C2 C3 C4 123.5(5) . . ?
F1 C3 C4 117.5(5) . . ?
C5 C4 C3 118.5(4) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
C6 C5 C4 119.1(4) . . ?
C6 C5 N1 120.3(4) . . ?
C4 C5 N1 120.7(4) . . ?
C5 C6 C1 120.7(4) . . ?
C5 C6 Cl1 120.4(3) . . ?
C1 C6 Cl1 118.9(4) . . ?
O1 C7 O2 124.8(4) . . ?
O1 C7 N1 126.4(4) . . ?
O2 C7 N1 108.9(3) . . ?
O2 C8 C9 105.7(4) . . ?
O2 C8 H8A 110.6 . . ?
C9 C8 H8A 110.6 . . ?
O2 C8 H8B 110.6 . . ?
C9 C8 H8B 110.6 . . ?
H8A C8 H8B 108.7 . . ?
C14 C9 C10 118.2(5) . . ?
C14 C9 C8 120.4(5) . . ?
C10 C9 C8 121.4(5) . . ?
C9 C10 C11 120.2(6) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 120.0(6) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C13 C12 C11 120.4(6) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 119.8(7) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C13 C14 C9 121.3(6) . . ?
C13 C14 H14 119.3 . . ?
C9 C14 H14 119.3 . . ?

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
C6 C1 C2 C3 -1.4(8) . . . . ?
C1 C2 C3 F1 -179.0(5) . . . . ?
C1 C2 C3 C4 0.1(9) . . . . ?
C2 C3 C4 C5 2.1(8) . . . . ?
F1 C3 C4 C5 -178.9(4) . . . . ?
C3 C4 C5 C6 -2.8(6) . . . . ?
C3 C4 C5 N1 179.0(4) . . . . ?
C7 N1 C5 C6 143.0(4) . . . . ?
C7 N1 C5 C4 -38.8(6) . . . . ?
C4 C5 C6 C1 1.5(6) . . . . ?
N1 C5 C6 C1 179.7(4) . . . . ?
C4 C5 C6 Cl1 180.0(3) . . . . ?
N1 C5 C6 Cl1 -1.9(5) . . . . ?
C2 C1 C6 C5 0.6(7) . . . . ?
C2 C1 C6 Cl1 -177.8(4) . . . . ?
C8 O2 C7 O1 -2.7(8) . . . . ?
C8 O2 C7 N1 176.8(5) . . . . ?
C5 N1 C7 O1 -3.1(7) . . . . ?
C5 N1 C7 O2 177.3(3) . . . . ?
C7 O2 C8 C9 173.5(4) . . . . ?
O2 C8 C9 C14 98.4(6) . . . . ?
O2 C8 C9 C10 -82.3(6) . . . . ?
C14 C9 C10 C11 -1.2(8) . . . . ?
C8 C9 C10 C11 179.4(5) . . . . ?
C9 C10 C11 C12 1.0(10) . . . . ?
C10 C11 C12 C13 -0.9(11) . . . . ?
C11 C12 C13 C14 0.9(12) . . . . ?
C12 C13 C14 C9 -1.1(11) . . . . ?
C10 C9 C14 C13 1.2(9) . . . . ?
C8 C9 C14 C13 -179.4(5) . . . . ?

_refine_diff_density_max         0.185
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.054



