# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_6155
_database_code_depnum_ccdc_archive 'CCDC 2051416'
loop_
_audit_author_name
_audit_author_address
NIKITA
;IIT GUWAHATI
India
;
_audit_update_record             
;
2020-12-19 deposited with the CCDC.	2021-07-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
2-(5-fluoro-2-(p-tolyl)-1H-indol-3-yl)ethene-1,1,2-tricarbonitrile
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H11 F N4'
_chemical_formula_weight         326.33

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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.4106(7)
_cell_length_b                   14.3958(14)
_cell_length_c                   9.9664(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.167(6)
_cell_angle_gamma                90
_cell_volume                     1632.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1572
_cell_measurement_theta_min      2.8230
_cell_measurement_theta_max      27.4520

_exptl_crystal_description       cube
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   0.977
_exptl_transmission_factor_max   0.980
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_detector                 'CCD plate'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7751
_diffrn_reflns_av_unetI/netI     0.0789
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.281
_diffrn_reflns_theta_max         28.743
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.874
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.874
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.874
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3709
_reflns_number_gt                1842
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_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)+(0.0488P)²] 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         3709
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1181
_refine_ls_R_factor_gt           0.0521
_refine_ls_wR_factor_ref         0.1383
_refine_ls_wR_factor_gt          0.1099
_refine_ls_goodness_of_fit_ref   0.952
_refine_ls_restrained_S_all      0.952
_refine_ls_shift/su_max          0.003
_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
F17 F -0.07415(13) 0.71290(11) 0.78640(15) 0.0751(5) Uani 1 1 d . . . . .
N9 N 0.24223(16) 0.48358(14) 1.04813(15) 0.0469(5) Uani 1 1 d . . . . .
H9 H 0.263325 0.475799 1.131977 0.056 Uiso 1 1 calc R U . . .
N21 N -0.03039(19) 0.40515(16) 0.59546(18) 0.0572(6) Uani 1 1 d . . . . .
N23 N 0.25739(17) 0.43169(17) 0.33938(17) 0.0589(6) Uani 1 1 d . . . . .
C3 C 0.14504(18) 0.53546(16) 0.85866(19) 0.0389(6) Uani 1 1 d . . . . .
C2 C 0.23122(19) 0.46821(17) 0.82486(18) 0.0394(6) Uani 1 1 d . . . . .
C18 C 0.26558(18) 0.44624(16) 0.69205(18) 0.0388(6) Uani 1 1 d . . . . .
C1 C 0.2897(2) 0.43818(17) 0.94643(19) 0.0422(6) Uani 1 1 d . . . . .
C19 C 0.19006(19) 0.43459(16) 0.58120(18) 0.0395(6) Uani 1 1 d . . . . .
C8 C 0.15535(19) 0.54408(17) 0.99950(19) 0.0429(6) Uani 1 1 d . . . . .
C20 C 0.0675(2) 0.41971(17) 0.59166(19) 0.0424(6) Uani 1 1 d . . . . .
C10 C 0.38548(19) 0.37141(18) 0.96895(19) 0.0427(6) Uani 1 1 d . . . . .
C22 C 0.22945(19) 0.43200(18) 0.4475(2) 0.0453(6) Uani 1 1 d . . . . .
C4 C 0.0666(2) 0.59513(17) 0.7852(2) 0.0473(6) Uani 1 1 d . . . . .
H4 H 0.058406 0.593564 0.691659 0.057 Uiso 1 1 calc R U . . .
C24 C 0.3899(2) 0.44496(19) 0.67232(19) 0.0490(7) Uani 1 1 d . . . . .
N25 N 0.4882(2) 0.4483(2) 0.6589(2) 0.0764(8) Uani 1 1 d . . . . .
C5 C 0.0033(2) 0.65522(19) 0.8565(2) 0.0535(7) Uani 1 1 d . . . . .
C7 C 0.0895(2) 0.60581(19) 1.0691(2) 0.0535(7) Uani 1 1 d . . . . .
H7 H 0.097680 0.609110 1.162502 0.064 Uiso 1 1 calc R U . . .
C11 C 0.4780(2) 0.39027(19) 1.0636(2) 0.0534(7) Uani 1 1 d . . . . .
H11 H 0.475865 0.442796 1.117646 0.064 Uiso 1 1 calc R U . . .
C15 C 0.3893(2) 0.29028(19) 0.8941(2) 0.0549(7) Uani 1 1 d . . . . .
H15 H 0.326977 0.275401 0.832531 0.066 Uiso 1 1 calc R U . . .
C6 C 0.0118(2) 0.66205(19) 0.9957(2) 0.0565(7) Uani 1 1 d . . . . .
H6 H -0.034595 0.704191 1.038756 0.068 Uiso 1 1 calc R U . . .
C12 C 0.5730(2) 0.3309(2) 1.0770(3) 0.0640(8) Uani 1 1 d . . . . .
H12 H 0.634482 0.344520 1.140339 0.077 Uiso 1 1 calc R U . . .
C13 C 0.5796(2) 0.2515(2) 0.9991(3) 0.0622(8) Uani 1 1 d . . . . .
C14 C 0.4845(2) 0.2318(2) 0.9103(2) 0.0631(8) Uani 1 1 d . . . . .
H14 H 0.484704 0.177366 0.859992 0.076 Uiso 1 1 calc R U . . .
C16 C 0.6856(2) 0.1892(2) 1.0139(3) 0.0968(11) Uani 1 1 d . . . . .
H16A H 0.754385 0.225884 1.037034 0.145 Uiso 1 1 calc R U . . .
H16B H 0.694527 0.157526 0.930462 0.145 Uiso 1 1 calc R U . . .
H16C H 0.675565 0.144479 1.083539 0.145 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
F17 C5 1.367(3) . ?
N9 C1 1.352(3) . ?
N9 C8 1.381(3) . ?
N21 C20 1.139(3) . ?
N23 C22 1.145(3) . ?
C3 C8 1.406(3) . ?
C3 C4 1.407(3) . ?
C3 C2 1.437(3) . ?
C2 C1 1.408(3) . ?
C2 C18 1.443(3) . ?
C18 C19 1.361(3) . ?
C18 C24 1.446(3) . ?
C1 C10 1.460(3) . ?
C19 C20 1.426(3) . ?
C19 C22 1.438(3) . ?
C8 C7 1.382(3) . ?
C10 C15 1.388(3) . ?
C10 C11 1.390(3) . ?
C4 C5 1.360(3) . ?
C24 N25 1.141(3) . ?
C5 C6 1.387(3) . ?
C7 C6 1.372(3) . ?
C11 C12 1.379(4) . ?
C15 C14 1.374(3) . ?
C12 C13 1.387(4) . ?
C13 C14 1.379(3) . ?
C13 C16 1.505(4) . ?

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
C1 N9 C8 111.01(17) . . ?
C8 C3 C4 118.0(2) . . ?
C8 C3 C2 106.53(18) . . ?
C4 C3 C2 135.17(19) . . ?
C1 C2 C3 107.15(18) . . ?
C1 C2 C18 125.4(2) . . ?
C3 C2 C18 126.79(18) . . ?
C19 C18 C2 125.0(2) . . ?
C19 C18 C24 117.22(18) . . ?
C2 C18 C24 117.53(17) . . ?
N9 C1 C2 107.8(2) . . ?
N9 C1 C10 122.63(18) . . ?
C2 C1 C10 129.6(2) . . ?
C18 C19 C20 121.70(19) . . ?
C18 C19 C22 122.2(2) . . ?
C20 C19 C22 115.98(17) . . ?
N9 C8 C7 129.2(2) . . ?
N9 C8 C3 107.5(2) . . ?
C7 C8 C3 123.3(2) . . ?
N21 C20 C19 177.0(3) . . ?
C15 C10 C11 118.5(2) . . ?
C15 C10 C1 121.6(2) . . ?
C11 C10 C1 119.9(2) . . ?
N23 C22 C19 177.6(3) . . ?
C5 C4 C3 117.2(2) . . ?
N25 C24 C18 176.7(3) . . ?
C4 C5 F17 117.8(2) . . ?
C4 C5 C6 124.5(2) . . ?
F17 C5 C6 117.6(2) . . ?
C6 C7 C8 117.8(2) . . ?
C12 C11 C10 119.8(3) . . ?
C14 C15 C10 120.5(2) . . ?
C7 C6 C5 119.1(2) . . ?
C11 C12 C13 122.0(2) . . ?
C14 C13 C12 117.2(3) . . ?
C14 C13 C16 122.0(3) . . ?
C12 C13 C16 120.8(3) . . ?
C15 C14 C13 121.8(3) . . ?

_refine_diff_density_max         0.168
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.039


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane'
_chemical_compound_source        NA
_chemical_properties_physical    Heat-sensitive
