# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_RAN_22_0m_a_a
_database_code_depnum_ccdc_archive 'CCDC 2258109'
loop_
_audit_author_name
_audit_author_address
'Rambabu Dandela'
;Institute of Chemical Technology IOC Bhubaneswar
India
;
_audit_update_record             
;
2023-04-21 deposited with the CCDC.	2023-06-12 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         'C24 H17 F2 N'
_chemical_formula_sum            'C24 H17 F2 N'
_chemical_formula_weight         357.39

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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   11.748(13)
_cell_length_b                   7.359(5)
_cell_length_c                   21.472(14)
_cell_angle_alpha                90
_cell_angle_beta                 94.50(3)
_cell_angle_gamma                90
_cell_volume                     1851(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2291
_cell_measurement_theta_min      0.979
_cell_measurement_theta_max      0.983

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_F_000             744.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_process_details   ?
_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 detector'
_diffrn_measurement_method       'Omega and Phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27658
_diffrn_reflns_av_unetI/netI     0.0590
_diffrn_reflns_av_R_equivalents  0.0996
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.927
_diffrn_reflns_theta_max         26.284
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3756
_reflns_number_gt                2291
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SHELXL'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1000P)²+0.9481P] 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         3738
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1073
_refine_ls_R_factor_gt           0.0588
_refine_ls_wR_factor_ref         0.2056
_refine_ls_wR_factor_gt          0.1487
_refine_ls_goodness_of_fit_ref   0.927
_refine_ls_restrained_S_all      0.927
_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
F2 F 0.07483(13) 0.9066(3) 0.66408(9) 0.0998(7) Uani 1 1 d . . . . .
F1 F 0.94808(17) 0.7281(3) 0.95455(8) 0.1041(7) Uani 1 1 d . . . . .
N1 N 0.60392(16) 0.7605(3) 0.71350(9) 0.0548(5) Uani 1 1 d . . . . .
C7 C 0.7175(2) 0.7310(3) 0.71522(11) 0.0524(6) Uani 1 1 d . . . . .
C4 C 0.7797(2) 0.7300(3) 0.77893(11) 0.0537(6) Uani 1 1 d . . . . .
C8 C 0.7734(2) 0.7030(3) 0.66151(11) 0.0560(6) Uani 1 1 d . . . . .
H8 H 0.851494 0.680148 0.664570 0.067 Uiso 1 1 calc R U . . .
C18 C 0.7720(2) 0.6840(3) 0.54475(11) 0.0556(6) Uani 1 1 d . . . . .
C12 C 0.4199(2) 0.8026(3) 0.65773(11) 0.0559(6) Uani 1 1 d . . . . .
C24 C 0.7205(2) 0.5911(4) 0.49328(11) 0.0637(7) Uani 1 1 d . . . . .
H24 H 0.647001 0.545264 0.494990 0.076 Uiso 1 1 calc R U . . .
C9 C 0.7132(2) 0.7090(3) 0.60289(11) 0.0544(6) Uani 1 1 d . . . . .
C11 C 0.5446(2) 0.7665(3) 0.65680(11) 0.0527(6) Uani 1 1 d . . . . .
C21 C 0.8868(2) 0.6313(4) 0.43476(12) 0.0644(7) Uani 1 1 d . . . . .
C13 C 0.3585(2) 0.8940(4) 0.60900(13) 0.0661(7) Uani 1 1 d . . . . .
H13 H 0.395691 0.931885 0.574587 0.079 Uiso 1 1 calc R U . . .
C10 C 0.5965(2) 0.7418(3) 0.60148(12) 0.0569(6) Uani 1 1 d . . . . .
H10 H 0.553120 0.747340 0.563394 0.068 Uiso 1 1 calc R U . . .
C3 C 0.8946(2) 0.7760(4) 0.78757(12) 0.0645(7) Uani 1 1 d . . . . .
H3 H 0.934014 0.807150 0.753192 0.077 Uiso 1 1 calc R U . . .
C23 C 0.7771(2) 0.5663(4) 0.43968(12) 0.0677(7) Uani 1 1 d . . . . .
H23 H 0.740536 0.504281 0.406084 0.081 Uiso 1 1 calc R U . . .
C19 C 0.8823(2) 0.7510(4) 0.53967(12) 0.0658(7) Uani 1 1 d . . . . .
H19 H 0.918933 0.814030 0.573009 0.079 Uiso 1 1 calc R U . . .
C20 C 0.9377(2) 0.7250(4) 0.48584(13) 0.0699(7) Uani 1 1 d . . . . .
H20 H 1.010975 0.771429 0.483771 0.084 Uiso 1 1 calc R U . . .
C5 C 0.7230(2) 0.6848(4) 0.83104(11) 0.0622(7) Uani 1 1 d . . . . .
H5 H 0.646058 0.653916 0.826109 0.075 Uiso 1 1 calc R U . . .
C17 C 0.3614(2) 0.7453(4) 0.70818(12) 0.0680(7) Uani 1 1 d . . . . .
H17 H 0.400720 0.682934 0.740830 0.082 Uiso 1 1 calc R U . . .
C15 C 0.1900(2) 0.8717(4) 0.66175(14) 0.0704(8) Uani 1 1 d . . . . .
C14 C 0.2424(2) 0.9293(4) 0.61124(15) 0.0737(8) Uani 1 1 d . . . . .
H14 H 0.201755 0.990851 0.578844 0.088 Uiso 1 1 calc R U . . .
C16 C 0.2454(2) 0.7794(5) 0.71074(14) 0.0778(9) Uani 1 1 d . . . . .
H16 H 0.206736 0.740952 0.744532 0.093 Uiso 1 1 calc R U . . .
C22 C 0.9478(3) 0.6042(5) 0.37628(14) 0.0896(10) Uani 1 1 d . . . . .
H22A H 0.914636 0.503044 0.353175 0.134 Uiso 1 1 calc R U . . .
H22B H 1.027124 0.580433 0.387373 0.134 Uiso 1 1 calc R U . . .
H22C H 0.940395 0.711865 0.351039 0.134 Uiso 1 1 calc R U . . .
C6 C 0.7788(2) 0.6848(4) 0.89018(13) 0.0711(7) Uani 1 1 d . . . . .
H6 H 0.740318 0.654882 0.924988 0.085 Uiso 1 1 calc R U . . .
C2 C 0.9517(2) 0.7763(4) 0.84691(14) 0.0722(8) Uani 1 1 d . . . . .
H2 H 1.028524 0.807401 0.852709 0.087 Uiso 1 1 calc R U . . .
C1 C 0.8915(3) 0.7297(4) 0.89616(13) 0.0708(8) 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
F2 C15 1.381(3) . ?
F1 C1 1.372(3) . ?
N1 C7 1.350(3) . ?
N1 C11 1.355(3) . ?
C7 C8 1.386(3) . ?
C7 C4 1.500(3) . ?
C4 C5 1.387(4) . ?
C4 C3 1.390(4) . ?
C8 C9 1.395(3) . ?
C18 C24 1.396(3) . ?
C18 C19 1.398(4) . ?
C18 C9 1.485(3) . ?
C12 C17 1.393(4) . ?
C12 C13 1.396(4) . ?
C12 C11 1.490(4) . ?
C24 C23 1.386(4) . ?
C9 C10 1.390(4) . ?
C11 C10 1.390(3) . ?
C21 C23 1.386(4) . ?
C21 C20 1.391(4) . ?
C21 C22 1.507(4) . ?
C13 C14 1.393(4) . ?
C3 C2 1.392(4) . ?
C19 C20 1.384(4) . ?
C5 C6 1.383(4) . ?
C17 C16 1.390(4) . ?
C15 C14 1.357(4) . ?
C15 C16 1.373(4) . ?
C6 C1 1.361(4) . ?
C2 C1 1.361(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
C7 N1 C11 117.9(2) . . ?
N1 C7 C8 122.2(2) . . ?
N1 C7 C4 115.8(2) . . ?
C8 C7 C4 122.0(2) . . ?
C5 C4 C3 118.3(2) . . ?
C5 C4 C7 120.4(2) . . ?
C3 C4 C7 121.3(2) . . ?
C7 C8 C9 120.4(2) . . ?
C24 C18 C19 117.2(2) . . ?
C24 C18 C9 121.7(2) . . ?
C19 C18 C9 121.1(2) . . ?
C17 C12 C13 118.2(2) . . ?
C17 C12 C11 120.1(2) . . ?
C13 C12 C11 121.7(2) . . ?
C23 C24 C18 121.0(2) . . ?
C10 C9 C8 117.0(2) . . ?
C10 C9 C18 121.7(2) . . ?
C8 C9 C18 121.2(2) . . ?
N1 C11 C10 122.3(2) . . ?
N1 C11 C12 115.5(2) . . ?
C10 C11 C12 122.2(2) . . ?
C23 C21 C20 117.1(2) . . ?
C23 C21 C22 121.6(3) . . ?
C20 C21 C22 121.3(3) . . ?
C14 C13 C12 120.9(3) . . ?
C11 C10 C9 120.2(2) . . ?
C4 C3 C2 121.0(3) . . ?
C21 C23 C24 121.8(3) . . ?
C20 C19 C18 121.1(3) . . ?
C19 C20 C21 121.7(3) . . ?
C6 C5 C4 121.2(3) . . ?
C16 C17 C12 121.4(3) . . ?
C14 C15 C16 123.3(3) . . ?
C14 C15 F2 118.6(3) . . ?
C16 C15 F2 118.1(3) . . ?
C15 C14 C13 118.5(3) . . ?
C15 C16 C17 117.8(3) . . ?
C1 C6 C5 118.3(3) . . ?
C1 C2 C3 117.9(3) . . ?
C6 C1 C2 123.2(2) . . ?
C6 C1 F1 118.8(3) . . ?
C2 C1 F1 117.9(3) . . ?

_refine_diff_density_max         0.173
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.041

