# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_6757
_audit_block_doi                 10.5517/ccdc.csd.cc228zt5
_database_code_depnum_ccdc_archive 'CCDC 1915267'
loop_
_audit_author_name
_audit_author_address
'Chao Gao'
;Huaqiao university
China
;
_audit_update_record             
;
2019-05-10 deposited with the CCDC.	2021-01-12 downloaded from the CCDC.
;
_audit_creation_date             2019-05-10
_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         'C21 H13 Cl F N O'
_chemical_formula_sum            'C21 H14 Cl F N O'
_chemical_formula_weight         350.78
_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'
N N 0.0061 0.0033 '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      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                   14.1901(8)
_cell_length_b                   13.1981(9)
_cell_length_c                   9.2973(6)
_cell_angle_alpha                90
_cell_angle_beta                 103.858(6)
_cell_angle_gamma                90
_cell_volume                     1690.54(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1415
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.9130
_cell_measurement_theta_min      4.2720
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.244
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24449
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             724
_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  0.0329
_diffrn_reflns_av_unetI/netI     0.0625
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.837
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8247
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.837
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.347
_diffrn_reflns_theta_min         3.356
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.837
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -53.00  35.00   1.00    8.00    --   15.49 -19.00 -30.00   88
  2  ω    -21.00  42.00   1.00    8.00    --   15.49 -99.00 -90.00   63
  3  ω    -24.00  23.00   1.00    8.00    --  -16.12 -99.00 -60.00   47
  4  ω    -23.00  12.00   1.00    8.00    --  -16.12 -99.00 150.00   35
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0502599000
_diffrn_orient_matrix_UB_12      0.0084882000
_diffrn_orient_matrix_UB_13      0.0299852000
_diffrn_orient_matrix_UB_21      -0.0095643000
_diffrn_orient_matrix_UB_22      0.0518686000
_diffrn_orient_matrix_UB_23      0.0099539000
_diffrn_orient_matrix_UB_31      -0.0060519000
_diffrn_orient_matrix_UB_32      -0.0108116000
_diffrn_orient_matrix_UB_33      0.0720508000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2057
_reflns_number_total             3894
_reflns_odcompleteness_completeness 99.48
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.920
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3894
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1221
_refine_ls_R_factor_gt           0.0549
_refine_ls_restrained_S_all      0.920
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1406
_refine_ls_wR_factor_ref         0.1912
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F), C00H(H00H),
 C00I(H00I), C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O),
 C00P(H00P)
;
_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
Cl01 Cl -0.05142(5) 0.37725(7) 0.24949(11) 0.0890(4) Uani 1 1 d . . . . .
O002 O 0.33163(13) 0.34172(15) 0.73314(19) 0.0579(5) Uani 1 1 d . . . . .
F003 F 0.05136(14) 0.35817(15) 0.8063(2) 0.0900(7) Uani 1 1 d . . . . .
N004 N 0.25056(18) 0.34316(19) 0.7937(3) 0.0632(7) Uani 1 1 d . . . . .
C005 C 0.39352(16) 0.39268(19) 0.3867(3) 0.0435(6) Uani 1 1 d . . . . .
C006 C 0.20456(18) 0.36050(19) 0.5406(3) 0.0457(6) Uani 1 1 d . . . . .
C007 C 0.30513(18) 0.35321(19) 0.5831(3) 0.0464(6) Uani 1 1 d . . . . .
C008 C 0.47959(17) 0.3732(2) 0.3268(3) 0.0458(6) Uani 1 1 d . . . . .
C009 C 0.31822(16) 0.4626(2) 0.3026(3) 0.0442(6) Uani 1 1 d . . . . .
C00A C 0.38656(18) 0.3505(2) 0.5151(3) 0.0491(7) Uani 1 1 d . . . . .
H00A H 0.4409 0.3152 0.5667 0.059 Uiso 1 1 calc R . . . .
C00B C 0.1768(2) 0.3544(2) 0.6773(3) 0.0530(7) Uani 1 1 d . . . . .
C00C C 0.28813(17) 0.5452(2) 0.3722(3) 0.0501(7) Uani 1 1 d . . . . .
H00C H 0.3177 0.5593 0.4707 0.060 Uiso 1 1 calc R . . . .
C00D C 0.53353(18) 0.2843(2) 0.3612(3) 0.0544(7) Uani 1 1 d . . . . .
H00D H 0.5137 0.2353 0.4195 0.065 Uiso 1 1 calc R . . . .
C00E C 0.13401(19) 0.3680(2) 0.4052(3) 0.0525(7) Uani 1 1 d . . . . .
H00E H 0.1516 0.3709 0.3151 0.063 Uiso 1 1 calc R . . . .
C00F C 0.51087(19) 0.4440(2) 0.2371(3) 0.0585(7) Uani 1 1 d . . . . .
H00F H 0.4760 0.5037 0.2117 0.070 Uiso 1 1 calc R . . . .
C00G C 0.0762(2) 0.3601(2) 0.6744(4) 0.0635(8) Uani 1 1 d . . . . .
C00H C 0.27480(19) 0.4447(2) 0.1536(3) 0.0584(7) Uani 1 1 d . . . . .
H00H H 0.2954 0.3907 0.1047 0.070 Uiso 1 1 calc R . . . .
C00I C 0.2141(2) 0.6066(2) 0.2951(3) 0.0622(8) Uani 1 1 d . . . . .
H00I H 0.1942 0.6618 0.3424 0.075 Uiso 1 1 calc R . . . .
C00J C 0.0399(2) 0.3707(2) 0.4118(3) 0.0595(8) Uani 1 1 d . . . . .
C00K C 0.6154(2) 0.2681(3) 0.3104(3) 0.0698(9) Uani 1 1 d . . . . .
H00K H 0.6510 0.2089 0.3358 0.084 Uiso 1 1 calc R . . . .
C00L C 0.6452(2) 0.3388(3) 0.2219(4) 0.0737(10) Uani 1 1 d . . . . .
H00L H 0.7004 0.3272 0.1871 0.088 Uiso 1 1 calc R . . . .
C00M C 0.5932(2) 0.4266(3) 0.1852(3) 0.0703(9) Uani 1 1 d . . . . .
H00M H 0.6132 0.4744 0.1253 0.084 Uiso 1 1 calc R . . . .
C00N C 0.0104(2) 0.3681(2) 0.5471(4) 0.0691(9) Uani 1 1 d . . . . .
H00N H -0.0551 0.3721 0.5464 0.083 Uiso 1 1 calc R . . . .
C00O C 0.1698(2) 0.5871(3) 0.1502(4) 0.0767(10) Uani 1 1 d . . . . .
H00O H 0.1188 0.6276 0.1003 0.092 Uiso 1 1 calc R . . . .
C00P C 0.2011(2) 0.5073(3) 0.0786(3) 0.0766(10) Uani 1 1 d . . . . .
H00P H 0.1725 0.4952 -0.0208 0.092 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
Cl01 C00J 1.740(3) . ?
O002 N004 1.397(3) . ?
O002 C007 1.364(3) . ?
F003 C00G 1.355(3) . ?
N004 C00B 1.321(3) . ?
C005 C008 1.481(3) . ?
C005 C009 1.485(3) . ?
C005 C00A 1.342(3) . ?
C006 C007 1.390(3) . ?
C006 C00B 1.419(4) . ?
C006 C00E 1.412(3) . ?
C007 C00A 1.444(3) . ?
C008 C00D 1.396(4) . ?
C008 C00F 1.394(4) . ?
C009 C00C 1.387(4) . ?
C009 C00H 1.394(4) . ?
C00A H00A 0.9300 . ?
C00B C00G 1.424(4) . ?
C00C H00C 0.9300 . ?
C00C C00I 1.383(4) . ?
C00D H00D 0.9300 . ?
C00D C00K 1.372(4) . ?
C00E H00E 0.9300 . ?
C00E C00J 1.352(4) . ?
C00F H00F 0.9300 . ?
C00F C00M 1.386(4) . ?
C00G C00N 1.325(4) . ?
C00H H00H 0.9300 . ?
C00H C00P 1.383(4) . ?
C00I H00I 0.9300 . ?
C00I C00O 1.368(4) . ?
C00J C00N 1.418(4) . ?
C00K H00K 0.9300 . ?
C00K C00L 1.376(5) . ?
C00L H00L 0.9300 . ?
C00L C00M 1.372(5) . ?
C00M H00M 0.9300 . ?
C00N H00N 0.9300 . ?
C00O H00O 0.9300 . ?
C00O C00P 1.375(4) . ?
C00P H00P 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
C007 O002 N004 111.0(2) . . ?
C00B N004 O002 103.77(19) . . ?
C008 C005 C009 117.6(2) . . ?
C00A C005 C008 120.4(2) . . ?
C00A C005 C009 121.9(2) . . ?
C007 C006 C00B 103.2(2) . . ?
C007 C006 C00E 135.9(2) . . ?
C00E C006 C00B 120.9(2) . . ?
O002 C007 C006 108.1(2) . . ?
O002 C007 C00A 113.0(2) . . ?
C006 C007 C00A 138.8(2) . . ?
C00D C008 C005 121.0(2) . . ?
C00F C008 C005 121.2(2) . . ?
C00F C008 C00D 117.7(2) . . ?
C00C C009 C005 120.4(2) . . ?
C00C C009 C00H 119.0(2) . . ?
C00H C009 C005 120.6(2) . . ?
C005 C00A C007 128.0(2) . . ?
C005 C00A H00A 116.0 . . ?
C007 C00A H00A 116.0 . . ?
N004 C00B C006 113.9(2) . . ?
N004 C00B C00G 127.9(3) . . ?
C006 C00B C00G 118.2(3) . . ?
C009 C00C H00C 120.0 . . ?
C00I C00C C009 119.9(3) . . ?
C00I C00C H00C 120.0 . . ?
C008 C00D H00D 119.5 . . ?
C00K C00D C008 121.0(3) . . ?
C00K C00D H00D 119.5 . . ?
C006 C00E H00E 121.4 . . ?
C00J C00E C006 117.3(3) . . ?
C00J C00E H00E 121.4 . . ?
C008 C00F H00F 119.6 . . ?
C00M C00F C008 120.9(3) . . ?
C00M C00F H00F 119.6 . . ?
F003 C00G C00B 117.4(3) . . ?
C00N C00G F003 122.0(3) . . ?
C00N C00G C00B 120.7(3) . . ?
C009 C00H H00H 120.0 . . ?
C00P C00H C009 120.1(3) . . ?
C00P C00H H00H 120.0 . . ?
C00C C00I H00I 119.5 . . ?
C00O C00I C00C 120.9(3) . . ?
C00O C00I H00I 119.5 . . ?
C00E C00J Cl01 120.0(2) . . ?
C00E C00J C00N 123.0(3) . . ?
C00N C00J Cl01 117.0(2) . . ?
C00D C00K H00K 119.8 . . ?
C00D C00K C00L 120.5(3) . . ?
C00L C00K H00K 119.8 . . ?
C00K C00L H00L 120.1 . . ?
C00M C00L C00K 119.9(3) . . ?
C00M C00L H00L 120.1 . . ?
C00F C00M H00M 120.0 . . ?
C00L C00M C00F 120.1(3) . . ?
C00L C00M H00M 120.0 . . ?
C00G C00N C00J 120.0(3) . . ?
C00G C00N H00N 120.0 . . ?
C00J C00N H00N 120.0 . . ?
C00I C00O H00O 120.2 . . ?
C00I C00O C00P 119.7(3) . . ?
C00P C00O H00O 120.2 . . ?
C00H C00P H00P 119.8 . . ?
C00O C00P C00H 120.4(3) . . ?
C00O C00P H00P 119.8 . . ?

_olex2_date_sample_data_collection 2019-05-10
_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 7.572
_oxdiff_exptl_absorpt_empirical_full_min 0.531
