# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_sks-4clcf3_auto
_database_code_depnum_ccdc_archive 'CCDC 2208817'
loop_
_audit_author_name
_audit_author_address
'Suman De Sarkar'
;IISER Kolkata
India
;
_audit_update_record             
;
2022-09-22 deposited with the CCDC.	2023-03-16 downloaded from the CCDC.
;
_audit_creation_date             2022-09-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H9 Cl F3 N O'
_chemical_formula_sum            'C11 H9 Cl F3 N O'
_chemical_formula_weight         263.64
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O Cl F'
_chemical_oxdiff_usercomment     100K
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'

_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                   14.0286(3)
_cell_length_b                   10.8221(2)
_cell_length_c                   7.36612(15)
_cell_angle_alpha                90
_cell_angle_beta                 102.292(2)
_cell_angle_gamma                90
_cell_volume                     1092.68(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7183
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      68.0020
_cell_measurement_theta_min      3.2130
_shelx_estimated_absorpt_T_max   0.936
_shelx_estimated_absorpt_T_min   0.850
_exptl_absorpt_coefficient_mu    3.370
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52119
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.58a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.603
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            9412
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.182
_diffrn_reflns_theta_min         3.224
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -85.00  -9.00   0.50    0.20    --  -40.33 121.00 -20.00  152
  2  ω    -47.00 -15.00   0.50    0.20    --  -82.50  42.00  30.00   64
  3  ω    -24.00  35.00   0.50    0.20    --  -40.33  12.00  60.00  118
  4  ω    -43.00  26.00   0.50    0.20    --  -40.33  38.00 150.00  138
  5  ω    -30.00  31.00   0.50    0.20    --   40.33 -25.00 150.00  122
  6  ω     97.00 163.00   0.50    0.20    --   96.67 121.00 -20.00  132
  7  ω     81.00 164.00   0.50    0.20    --   96.67 145.00 -60.00  166
  8  ω     99.00 164.00   0.50    0.20    --   96.67 117.00-180.00  130
  9  ω    105.00 170.00   0.50    0.20    --   96.67  96.00 -60.00  130
 10  ω    105.00 170.00   0.50    0.20    --   96.67  96.00 -30.00  130
 11  ω     83.00 164.00   0.50    0.20    --   96.67  33.00 150.00  162
 12  ω     14.00 109.00   0.50    0.20    --   40.33  77.00 -60.00  190
 13  ω    -30.00  31.00   0.50    0.20    --   40.33 -25.00-150.00  122
 14  ω    -26.00  43.00   0.50    0.20    --   40.33 -38.00 -90.00  138
 15  ω     28.00 105.00   0.50    0.20    --   96.67 -77.00-180.00  154
 16  ω     29.00  68.00   0.50    0.20    --   96.67 -59.00-120.00   78
 17  ω     30.00  57.00   0.50    0.20    --   96.67 -50.00 -90.00   54
 18  ω     29.00  68.00   0.50    0.20    --   96.67 -59.00 -60.00   78
 19  ω     30.00  57.00   0.50    0.20    --   96.67 -50.00  30.00   54
 20  ω     30.00  57.00   0.50    0.20    --   96.67 -50.00  60.00   54
 21  ω     30.00  57.00   0.50    0.20    --   96.67 -50.00  90.00   54
 22  ω     30.00  57.00   0.50    0.20    --   96.67 -50.00 120.00   54
 23  ω     22.00 106.00   0.50    0.20    --   96.67 -96.00  60.00  168
 24  ω     49.00 110.00   0.50    0.20    --   40.33-154.00  98.00  122
 25  ω     49.00 132.00   0.50    0.20    --   96.67-154.00  98.00  166
 26  ω     44.00 127.00   0.50    0.20    --   96.67-145.00   0.00  166
 27  ω     31.00 111.00   0.50    0.20    --   96.67-121.00-103.00  160
 28  ω     31.00  88.00   0.50    0.20    --   40.33-121.00-103.00  114
 29  ω   -109.00 -13.00   0.50    0.20    --  -40.33 -77.00 -30.00  192
 30  ω   -108.00 -17.00   0.50    0.20    --  -40.33 -64.00   0.00  182
 31  ω   -108.00 -17.00   0.50    0.20    --  -40.33 -64.00  90.00  182
 32  ω   -109.00 -13.00   0.50    0.20    --  -40.33 -77.00 150.00  192
 33  ω   -107.00 -21.00   0.50    0.20    --  -40.33 -50.00  30.00  172
 34  ω   -108.00 -17.00   0.50    0.20    --  -40.33 -64.00-180.00  182
 35  ω   -107.00 -21.00   0.50    0.20    --  -40.33 -50.00-150.00  172
 36  ω   -153.00 -68.00   0.50    0.20    --  -82.50 -25.00 -90.00  170
 37  ω   -149.00 -75.00   0.50    0.20    --  -82.50-121.00-103.00  148
 38  ω   -109.00 -53.00   0.50    0.20    --  -40.33-154.00  98.00  112
 39  ω   -147.00 -53.00   0.50    0.20    --  -82.50-154.00  98.00  188
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0984164000
_diffrn_orient_matrix_UB_12      0.0667967000
_diffrn_orient_matrix_UB_13      0.0162956000
_diffrn_orient_matrix_UB_21      0.0537414000
_diffrn_orient_matrix_UB_22      -0.1246549000
_diffrn_orient_matrix_UB_23      0.0358410000
_diffrn_orient_matrix_UB_31      -0.0075045000
_diffrn_orient_matrix_UB_32      -0.0160932000
_diffrn_orient_matrix_UB_33      -0.2104114000
_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                1873
_reflns_number_total             1981
_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 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.521
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.0013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1981
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0385
_refine_ls_restrained_S_all      1.043
_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)+(0.0559P)²+0.7809P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1038
_refine_ls_wR_factor_ref         0.1049
_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:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C3(H3), C6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.06553(4) 0.16804(5) 0.76687(7) 0.0376(2) Uani 1 1 d . . . . .
F3 F -0.76180(9) 0.12586(12) 0.21618(17) 0.0378(3) Uani 1 1 d . . . . .
F1 F -0.70789(9) 0.11310(12) -0.03390(15) 0.0353(3) Uani 1 1 d . . . . .
N1 N -0.39079(11) 0.30618(14) 0.3038(2) 0.0225(4) Uani 1 1 d . . . . .
F2 F -0.69305(8) 0.28298(10) 0.11833(16) 0.0305(3) Uani 1 1 d . . . . .
O1 O -0.48722(9) 0.28651(11) 0.20167(19) 0.0254(3) Uani 1 1 d . . . . .
C2 C -0.19111(15) 0.30209(18) 0.5008(3) 0.0247(4) Uani 1 1 d . . . . .
H2 H -0.219937 0.380964 0.470980 0.030 Uiso 1 1 calc R U . . .
C1 C -0.24577(14) 0.19536(17) 0.4456(2) 0.0202(4) Uani 1 1 d . . . . .
C4 C -0.05399(14) 0.17847(19) 0.6408(3) 0.0264(4) Uani 1 1 d . . . . .
C8 C -0.40971(15) 0.09265(18) 0.2717(3) 0.0305(5) Uani 1 1 d . . . . .
H8A H -0.419952 0.039489 0.375284 0.037 Uiso 1 1 calc R U . . .
H8B H -0.380639 0.042728 0.184740 0.037 Uiso 1 1 calc R U . . .
C5 C -0.10580(14) 0.07136(19) 0.5874(3) 0.0275(4) Uani 1 1 d . . . . .
H5 H -0.076383 -0.007158 0.617460 0.033 Uiso 1 1 calc R U . . .
C7 C -0.34710(13) 0.20236(16) 0.3421(2) 0.0197(4) Uani 1 1 d . . . . .
C3 C -0.09558(15) 0.29402(19) 0.5983(3) 0.0280(4) Uani 1 1 d . . . . .
H3 H -0.058798 0.366809 0.635829 0.034 Uiso 1 1 calc R U . . .
C6 C -0.20197(14) 0.08034(18) 0.4886(3) 0.0242(4) Uani 1 1 d . . . . .
H6 H -0.238137 0.007239 0.450091 0.029 Uiso 1 1 calc R U . . .
C10 C -0.59215(14) 0.11623(17) 0.2510(2) 0.0245(4) Uani 1 1 d . . . . .
H10A H -0.593827 0.024995 0.259665 0.029 Uiso 1 1 calc R U . . .
H10B H -0.583729 0.149713 0.378474 0.029 Uiso 1 1 calc R U . . .
C9 C -0.50488(14) 0.15343(17) 0.1725(3) 0.0254(4) Uani 1 1 d . . . . .
H9 H -0.517560 0.134102 0.036681 0.030 Uiso 1 1 calc R U . . .
C11 C -0.68798(14) 0.16027(17) 0.1380(3) 0.0236(4) Uani 1 1 d . . . . .


_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 1.739(2) . ?
F3 C11 1.341(2) . ?
F1 C11 1.338(2) . ?
N1 O1 1.417(2) . ?
N1 C7 1.282(2) . ?
F2 C11 1.336(2) . ?
O1 C9 1.469(2) . ?
C2 H2 0.9500 . ?
C2 C1 1.398(3) . ?
C2 C3 1.382(3) . ?
C1 C7 1.465(3) . ?
C1 C6 1.394(3) . ?
C4 C5 1.380(3) . ?
C4 C3 1.387(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C7 1.502(3) . ?
C8 C9 1.528(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.393(3) . ?
C3 H3 0.9500 . ?
C6 H6 0.9500 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C9 1.516(3) . ?
C10 C11 1.500(3) . ?
C9 H9 1.0000 . ?

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 N1 O1 110.04(14) . . ?
N1 O1 C9 109.71(12) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C3 C2 C1 120.67(18) . . ?
C2 C1 C7 121.33(17) . . ?
C6 C1 C2 118.92(18) . . ?
C6 C1 C7 119.74(16) . . ?
C5 C4 Cl1 119.15(16) . . ?
C5 C4 C3 121.48(18) . . ?
C3 C4 Cl1 119.37(15) . . ?
H8A C8 H8B 109.2 . . ?
C7 C8 H8A 111.3 . . ?
C7 C8 H8B 111.3 . . ?
C7 C8 C9 102.25(15) . . ?
C9 C8 H8A 111.3 . . ?
C9 C8 H8B 111.3 . . ?
C4 C5 H5 120.6 . . ?
C4 C5 C6 118.87(18) . . ?
C6 C5 H5 120.6 . . ?
N1 C7 C1 121.68(16) . . ?
N1 C7 C8 113.56(16) . . ?
C1 C7 C8 124.76(16) . . ?
C2 C3 C4 119.28(18) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C1 C6 H6 119.6 . . ?
C5 C6 C1 120.78(18) . . ?
C5 C6 H6 119.6 . . ?
H10A C10 H10B 107.7 . . ?
C9 C10 H10A 108.8 . . ?
C9 C10 H10B 108.8 . . ?
C11 C10 H10A 108.8 . . ?
C11 C10 H10B 108.8 . . ?
C11 C10 C9 113.90(15) . . ?
O1 C9 C8 104.42(15) . . ?
O1 C9 C10 109.22(15) . . ?
O1 C9 H9 109.9 . . ?
C8 C9 H9 109.9 . . ?
C10 C9 C8 113.43(17) . . ?
C10 C9 H9 109.9 . . ?
F3 C11 C10 110.88(15) . . ?
F1 C11 F3 106.01(16) . . ?
F1 C11 C10 112.68(15) . . ?
F2 C11 F3 107.12(15) . . ?
F2 C11 F1 106.32(15) . . ?
F2 C11 C10 113.37(16) . . ?

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 179.11(14) . . . . ?
Cl1 C4 C3 C2 -178.91(14) . . . . ?
N1 O1 C9 C8 1.3(2) . . . . ?
N1 O1 C9 C10 122.97(15) . . . . ?
O1 N1 C7 C1 179.40(14) . . . . ?
O1 N1 C7 C8 -0.8(2) . . . . ?
C2 C1 C7 N1 -2.5(3) . . . . ?
C2 C1 C7 C8 177.70(18) . . . . ?
C2 C1 C6 C5 1.0(3) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
C4 C5 C6 C1 -0.6(3) . . . . ?
C5 C4 C3 C2 0.2(3) . . . . ?
C7 N1 O1 C9 -0.4(2) . . . . ?
C7 C1 C6 C5 -179.81(16) . . . . ?
C7 C8 C9 O1 -1.6(2) . . . . ?
C7 C8 C9 C10 -120.45(17) . . . . ?
C3 C2 C1 C7 -179.97(16) . . . . ?
C3 C2 C1 C6 -0.8(3) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C6 C1 C7 N1 178.26(16) . . . . ?
C6 C1 C7 C8 -1.5(3) . . . . ?
C9 C8 C7 N1 1.6(2) . . . . ?
C9 C8 C7 C1 -178.63(16) . . . . ?
C9 C10 C11 F3 -179.13(15) . . . . ?
C9 C10 C11 F1 62.2(2) . . . . ?
C9 C10 C11 F2 -58.6(2) . . . . ?
C11 C10 C9 O1 72.5(2) . . . . ?
C11 C10 C9 C8 -171.54(16) . . . . ?

_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 2.006
_oxdiff_exptl_absorpt_empirical_full_min 0.659
