# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_KB26_0m
_database_code_depnum_ccdc_archive 'CCDC 2072978'
loop_
_audit_author_name
_audit_author_address
'Sravani Sana'
;NIPER Hyderabad
India
;
_audit_update_record             
;
2021-03-25 deposited with the CCDC.	2023-08-08 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         'C21 H12 Cl F N2'
_chemical_formula_sum            'C21 H12 Cl F N2'
_chemical_formula_weight         346.78

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'
N N 0.0061 0.0033 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   7.6674(19)
_cell_length_b                   9.375(2)
_cell_length_c                   12.301(2)
_cell_angle_alpha                72.479(5)
_cell_angle_beta                 83.153(6)
_cell_angle_gamma                75.425(6)
_cell_volume                     815.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7654
_cell_measurement_theta_min      2.341
_cell_measurement_theta_max      30.500

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_F_000             356
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.250
_shelx_estimated_absorpt_T_min   0.920
_shelx_estimated_absorpt_T_max   0.940
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6710
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16983
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.340
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3719
_reflns_number_gt                2970
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_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)+(0.0402P)²+0.2783P] 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_number_reflns         3719
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.1089
_refine_ls_wR_factor_gt          0.1007
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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
C1 C 0.20411(19) 0.33637(17) 0.47544(13) 0.0359(3) Uani 1 1 d . . . . .
C2 C 0.1699(2) 0.2250(2) 0.43010(16) 0.0462(4) Uani 1 1 d . . . . .
H2 H 0.147003 0.133521 0.478678 0.055 Uiso 1 1 calc R U . . .
C3 C 0.1704(3) 0.2519(2) 0.31566(17) 0.0532(5) Uani 1 1 d . . . . .
H3 H 0.145634 0.179625 0.285553 0.064 Uiso 1 1 calc R U . . .
C4 C 0.2086(3) 0.3893(2) 0.24185(15) 0.0523(5) Uani 1 1 d . . . . .
H4 H 0.212017 0.405268 0.163335 0.063 Uiso 1 1 calc R U . . .
C5 C 0.2401(2) 0.4974(2) 0.28293(13) 0.0443(4) Uani 1 1 d . . . . .
H5 H 0.265982 0.587109 0.233408 0.053 Uiso 1 1 calc R U . . .
C6 C 0.25799(18) 0.56267(17) 0.46635(12) 0.0319(3) Uani 1 1 d . . . . .
C7 C 0.24637(18) 0.47037(16) 0.57838(12) 0.0320(3) Uani 1 1 d . . . . .
C8 C 0.26785(19) 0.52354(17) 0.67164(12) 0.0333(3) Uani 1 1 d . . . . .
C9 C 0.2518(2) 0.43680(19) 0.78640(13) 0.0410(4) Uani 1 1 d . . . . .
H9 H 0.229717 0.339135 0.803360 0.049 Uiso 1 1 calc R U . . .
C10 C 0.2683(2) 0.4952(2) 0.87279(13) 0.0471(4) Uani 1 1 d . . . . .
H10 H 0.258203 0.437636 0.948440 0.057 Uiso 1 1 calc R U . . .
C11 C 0.3006(2) 0.6422(2) 0.84652(14) 0.0448(4) Uani 1 1 d . . . . .
C12 C 0.3192(2) 0.72973(19) 0.73664(13) 0.0420(4) Uani 1 1 d . . . . .
H12 H 0.342397 0.826682 0.721875 0.050 Uiso 1 1 calc R U . . .
C13 C 0.3030(2) 0.67187(17) 0.64538(12) 0.0350(3) Uani 1 1 d . . . . .
C14 C 0.3121(2) 0.76228(18) 0.52907(13) 0.0375(3) Uani 1 1 d . . . . .
H14 H 0.337134 0.858667 0.513844 0.045 Uiso 1 1 calc R U . . .
C15 C 0.2859(2) 0.71377(17) 0.43897(12) 0.0344(3) Uani 1 1 d . . . . .
C16 C 0.2726(2) 0.82070(17) 0.32127(12) 0.0345(3) Uani 1 1 d . . . . .
C17 C 0.1110(2) 0.86212(19) 0.26598(13) 0.0427(4) Uani 1 1 d . . . . .
H17 H 0.014156 0.820539 0.302298 0.051 Uiso 1 1 calc R U . . .
C18 C 0.0930(3) 0.9641(2) 0.15805(14) 0.0477(4) Uani 1 1 d . . . . .
H18 H -0.014797 0.991964 0.121311 0.057 Uiso 1 1 calc R U . . .
C19 C 0.2380(3) 1.0228(2) 0.10673(13) 0.0475(4) Uani 1 1 d . . . . .
C20 C 0.3985(3) 0.9857(2) 0.15733(14) 0.0488(4) Uani 1 1 d . . . . .
H20 H 0.494495 1.027644 0.119774 0.059 Uiso 1 1 calc R U . . .
C21 C 0.4156(2) 0.88396(19) 0.26612(13) 0.0409(4) Uani 1 1 d . . . . .
H21 H 0.523705 0.858083 0.302228 0.049 Uiso 1 1 calc R U . . .
N1 N 0.21158(17) 0.33186(14) 0.58361(11) 0.0363(3) Uani 1 1 d . . . . .
N2 N 0.23367(16) 0.47392(14) 0.39938(10) 0.0337(3) Uani 1 1 d . . . . .
F1 F 0.22003(19) 1.12372(15) 0.00040(9) 0.0767(4) Uani 1 1 d . . . . .
Cl1 Cl 0.32013(8) 0.71324(6) 0.95944(4) 0.06782(19) 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
C1 N1 1.3263(19) . ?
C1 N2 1.3999(19) . ?
C1 C2 1.412(2) . ?
C2 C3 1.353(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.412(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.342(2) . ?
C4 H4 0.9300 . ?
C5 N2 1.3790(19) . ?
C5 H5 0.9300 . ?
C6 N2 1.3904(19) . ?
C6 C7 1.3955(19) . ?
C6 C15 1.419(2) . ?
C7 N1 1.3715(19) . ?
C7 C8 1.422(2) . ?
C8 C9 1.410(2) . ?
C8 C13 1.417(2) . ?
C9 C10 1.365(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.396(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.366(2) . ?
C11 Cl1 1.7468(17) . ?
C12 C13 1.416(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.431(2) . ?
C14 C15 1.371(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.490(2) . ?
C16 C21 1.386(2) . ?
C16 C17 1.396(2) . ?
C17 C18 1.381(2) . ?
C17 H17 0.9300 . ?
C18 C19 1.367(3) . ?
C18 H18 0.9300 . ?
C19 F1 1.3629(18) . ?
C19 C20 1.364(3) . ?
C20 C21 1.389(2) . ?
C20 H20 0.9300 . ?
C21 H21 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
N1 C1 N2 112.56(13) . . ?
N1 C1 C2 129.13(15) . . ?
N2 C1 C2 118.30(14) . . ?
C3 C2 C1 119.70(17) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 120.18(17) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 121.18(16) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 N2 119.29(16) . . ?
C4 C5 H5 120.4 . . ?
N2 C5 H5 120.4 . . ?
N2 C6 C7 104.69(13) . . ?
N2 C6 C15 132.48(13) . . ?
C7 C6 C15 122.82(13) . . ?
N1 C7 C6 112.20(13) . . ?
N1 C7 C8 127.18(13) . . ?
C6 C7 C8 120.62(13) . . ?
C9 C8 C13 119.98(14) . . ?
C9 C8 C7 122.82(14) . . ?
C13 C8 C7 117.19(13) . . ?
C10 C9 C8 120.43(15) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 119.39(15) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C12 C11 C10 122.22(15) . . ?
C12 C11 Cl1 119.75(14) . . ?
C10 C11 Cl1 118.02(13) . . ?
C11 C12 C13 119.57(15) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C12 C13 C8 118.40(13) . . ?
C12 C13 C14 121.58(14) . . ?
C8 C13 C14 119.94(14) . . ?
C15 C14 C13 123.19(14) . . ?
C15 C14 H14 118.4 . . ?
C13 C14 H14 118.4 . . ?
C14 C15 C6 116.14(13) . . ?
C14 C15 C16 120.67(13) . . ?
C6 C15 C16 122.99(13) . . ?
C21 C16 C17 118.86(14) . . ?
C21 C16 C15 121.58(14) . . ?
C17 C16 C15 119.54(13) . . ?
C18 C17 C16 120.91(15) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C19 C18 C17 118.17(16) . . ?
C19 C18 H18 120.9 . . ?
C17 C18 H18 120.9 . . ?
F1 C19 C20 118.81(16) . . ?
F1 C19 C18 118.16(17) . . ?
C20 C19 C18 123.03(15) . . ?
C19 C20 C21 118.59(15) . . ?
C19 C20 H20 120.7 . . ?
C21 C20 H20 120.7 . . ?
C16 C21 C20 120.44(15) . . ?
C16 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C1 N1 C7 104.44(12) . . ?
C5 N2 C6 132.64(13) . . ?
C5 N2 C1 121.24(14) . . ?
C6 N2 C1 106.08(12) . . ?

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
N1 C1 C2 C3 -179.20(16) . . . . ?
N2 C1 C2 C3 1.5(2) . . . . ?
C1 C2 C3 C4 1.2(3) . . . . ?
C2 C3 C4 C5 -1.8(3) . . . . ?
C3 C4 C5 N2 -0.5(3) . . . . ?
N2 C6 C7 N1 -1.61(16) . . . . ?
C15 C6 C7 N1 177.43(13) . . . . ?
N2 C6 C7 C8 179.04(12) . . . . ?
C15 C6 C7 C8 -1.9(2) . . . . ?
N1 C7 C8 C9 -1.3(2) . . . . ?
C6 C7 C8 C9 177.96(14) . . . . ?
N1 C7 C8 C13 -179.88(13) . . . . ?
C6 C7 C8 C13 -0.6(2) . . . . ?
C13 C8 C9 C10 0.5(2) . . . . ?
C7 C8 C9 C10 -178.03(15) . . . . ?
C8 C9 C10 C11 0.3(3) . . . . ?
C9 C10 C11 C12 -1.0(3) . . . . ?
C9 C10 C11 Cl1 179.76(13) . . . . ?
C10 C11 C12 C13 0.9(3) . . . . ?
Cl1 C11 C12 C13 -179.88(12) . . . . ?
C11 C12 C13 C8 -0.1(2) . . . . ?
C11 C12 C13 C14 176.74(15) . . . . ?
C9 C8 C13 C12 -0.6(2) . . . . ?
C7 C8 C13 C12 178.01(13) . . . . ?
C9 C8 C13 C14 -177.51(14) . . . . ?
C7 C8 C13 C14 1.1(2) . . . . ?
C12 C13 C14 C15 -175.83(15) . . . . ?
C8 C13 C14 C15 0.9(2) . . . . ?
C13 C14 C15 C6 -3.3(2) . . . . ?
C13 C14 C15 C16 171.72(14) . . . . ?
N2 C6 C15 C14 -177.43(14) . . . . ?
C7 C6 C15 C14 3.8(2) . . . . ?
N2 C6 C15 C16 7.7(2) . . . . ?
C7 C6 C15 C16 -171.09(14) . . . . ?
C14 C15 C16 C21 62.9(2) . . . . ?
C6 C15 C16 C21 -122.45(17) . . . . ?
C14 C15 C16 C17 -115.28(17) . . . . ?
C6 C15 C16 C17 59.4(2) . . . . ?
C21 C16 C17 C18 0.1(2) . . . . ?
C15 C16 C17 C18 178.33(15) . . . . ?
C16 C17 C18 C19 0.2(3) . . . . ?
C17 C18 C19 F1 -179.78(16) . . . . ?
C17 C18 C19 C20 -0.2(3) . . . . ?
F1 C19 C20 C21 179.37(15) . . . . ?
C18 C19 C20 C21 -0.2(3) . . . . ?
C17 C16 C21 C20 -0.6(2) . . . . ?
C15 C16 C21 C20 -178.72(15) . . . . ?
C19 C20 C21 C16 0.6(3) . . . . ?
N2 C1 N1 C7 0.20(16) . . . . ?
C2 C1 N1 C7 -179.16(15) . . . . ?
C6 C7 N1 C1 0.90(16) . . . . ?
C8 C7 N1 C1 -179.81(14) . . . . ?
C4 C5 N2 C6 -179.37(15) . . . . ?
C4 C5 N2 C1 3.3(2) . . . . ?
C7 C6 N2 C5 -176.00(15) . . . . ?
C15 C6 N2 C5 5.1(3) . . . . ?
C7 C6 N2 C1 1.61(14) . . . . ?
C15 C6 N2 C1 -177.29(15) . . . . ?
N1 C1 N2 C5 176.76(13) . . . . ?
C2 C1 N2 C5 -3.8(2) . . . . ?
N1 C1 N2 C6 -1.19(16) . . . . ?
C2 C1 N2 C6 178.24(13) . . . . ?

_refine_diff_density_max         0.248
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.037



