# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2002738'
loop_
_audit_author_name
_audit_author_address
'Anand Singh'
;IIT Kanpur
India
;
_audit_update_record             
;
2020-05-08 deposited with the CCDC.	2020-10-30 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         'C26 H24 F N3'
_chemical_formula_sum            'C26 H24 F N3'
_chemical_formula_weight         397.48

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   5.6056(6)
_cell_length_b                   17.422(2)
_cell_length_c                   22.161(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2164.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2838
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      26.39

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6644
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14992
_diffrn_reflns_av_unetI/netI     0.1182
_diffrn_reflns_av_R_equivalents  0.1371
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.178
_diffrn_reflns_theta_max         25.263
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             3856
_reflns_number_gt                2713
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.716
_reflns_Friedel_fraction_max     0.982
_reflns_Friedel_fraction_full    0.983

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_molecular_graphics    'Bruker SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'Bruker SHELXTL (Sheldrick, 2008)'
_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)+(0.0349P)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_abs_structure_details 
;
 Flack x determined using 635 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(10)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3856
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1026
_refine_ls_R_factor_gt           0.0684
_refine_ls_wR_factor_ref         0.1217
_refine_ls_wR_factor_gt          0.1064
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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
F1 F 0.4256(5) 0.06659(18) 0.20306(12) 0.0415(8) Uani 1 1 d . . . . .
N1 N 0.5993(6) 0.1737(3) 0.29933(17) 0.0289(10) Uani 1 1 d . . . . .
N2 N 0.3616(6) 0.1679(2) 0.29742(16) 0.0249(10) Uani 1 1 d . . . . .
N3 N 0.2529(6) 0.1611(2) 0.35072(16) 0.0229(10) Uani 1 1 d . . . . .
C1 C 0.6468(7) 0.1708(3) 0.35821(19) 0.0255(12) Uani 1 1 d . . . . .
H1A H 0.801152 0.174285 0.375703 0.031 Uiso 1 1 calc R U . . .
C2 C 0.4341(7) 0.1620(3) 0.39010(18) 0.0215(11) Uani 1 1 d . . . . .
C3 C 0.3926(7) 0.1520(3) 0.45551(19) 0.0221(12) Uani 1 1 d . . . . .
C4 C 0.5604(7) 0.1782(3) 0.49710(19) 0.0235(11) Uani 1 1 d . . . . .
H4A H 0.699972 0.203758 0.483404 0.028 Uiso 1 1 calc R U . . .
C5 C 0.5243(8) 0.1671(3) 0.5586(2) 0.0271(12) Uani 1 1 d . . . . .
H5A H 0.639731 0.185599 0.586446 0.033 Uiso 1 1 calc R U . . .
C6 C 0.3241(8) 0.1299(3) 0.5800(2) 0.0255(12) Uani 1 1 d . . . . .
C7 C 0.1560(8) 0.1047(3) 0.5382(2) 0.0257(12) Uani 1 1 d . . . . .
H7A H 0.016362 0.079265 0.551968 0.031 Uiso 1 1 calc R U . . .
C8 C 0.1883(7) 0.1159(3) 0.4768(2) 0.0242(12) Uani 1 1 d . . . . .
H8A H 0.070155 0.098829 0.449165 0.029 Uiso 1 1 calc R U . . .
C9 C 0.2921(9) 0.1141(4) 0.6466(2) 0.0369(15) Uani 1 1 d . . . . .
H9A H 0.123219 0.104306 0.655042 0.055 Uiso 1 1 calc R U . . .
H9B H 0.345689 0.158695 0.669871 0.055 Uiso 1 1 calc R U . . .
H9C H 0.386586 0.069050 0.657985 0.055 Uiso 1 1 calc R U . . .
C10 C 0.2253(8) 0.1765(3) 0.24154(19) 0.0246(12) Uani 1 1 d . . . . .
H10A H 0.073787 0.146789 0.246186 0.030 Uiso 1 1 calc R U . . .
C11 C 0.1590(7) 0.2592(3) 0.22905(19) 0.0204(12) Uani 1 1 d . . . . .
C12 C 0.3069(7) 0.3186(3) 0.2445(2) 0.0270(13) Uani 1 1 d . . . . .
H12A H 0.452244 0.308246 0.265050 0.032 Uiso 1 1 calc R U . . .
C13 C 0.2459(9) 0.3946(3) 0.2304(2) 0.0328(14) Uani 1 1 d . . . . .
H13A H 0.349383 0.435292 0.241734 0.039 Uiso 1 1 calc R U . . .
C14 C 0.0360(8) 0.4106(3) 0.2001(2) 0.0279(12) Uani 1 1 d . . . . .
C15 C -0.1130(8) 0.3504(3) 0.1847(2) 0.0313(14) Uani 1 1 d . . . . .
H15A H -0.258172 0.360567 0.164047 0.038 Uiso 1 1 calc R U . . .
C16 C -0.0520(8) 0.2751(3) 0.1991(2) 0.0283(13) Uani 1 1 d . . . . .
H16A H -0.156066 0.234319 0.188260 0.034 Uiso 1 1 calc R U . . .
C17 C -0.0307(10) 0.4912(3) 0.1836(2) 0.0463(16) Uani 1 1 d . . . . .
H17A H 0.101331 0.525861 0.193560 0.069 Uiso 1 1 calc R U . . .
H17B H -0.173215 0.506526 0.206250 0.069 Uiso 1 1 calc R U . . .
H17C H -0.063939 0.494015 0.140265 0.069 Uiso 1 1 calc R U . . .
C18 C 0.3640(8) 0.1411(3) 0.1901(2) 0.0265(12) Uani 1 1 d . . . . .
C19 C 0.4150(7) 0.1709(3) 0.13769(19) 0.0276(13) Uani 1 1 d . . . . .
H19A H 0.358406 0.221739 0.131560 0.033 Uiso 1 1 calc R U . . .
C20 C 0.5475(8) 0.1375(3) 0.08643(19) 0.0269(12) Uani 1 1 d . . . . .
C21 C 0.5063(8) 0.1652(3) 0.0292(2) 0.0364(14) Uani 1 1 d . . . . .
H21A H 0.389028 0.203873 0.023365 0.044 Uiso 1 1 calc R U . . .
C22 C 0.6322(9) 0.1379(3) -0.0201(2) 0.0370(14) Uani 1 1 d . . . . .
H22A H 0.597394 0.157223 -0.059207 0.044 Uiso 1 1 calc R U . . .
C23 C 0.8082(8) 0.0829(3) -0.0131(2) 0.0299(14) Uani 1 1 d . . . . .
C24 C 0.8521(9) 0.0559(4) 0.0444(2) 0.0394(15) Uani 1 1 d . . . . .
H24A H 0.973274 0.018559 0.050358 0.047 Uiso 1 1 calc R U . . .
C25 C 0.7229(9) 0.0822(4) 0.0937(2) 0.0376(15) Uani 1 1 d . . . . .
H25A H 0.754954 0.062091 0.132737 0.045 Uiso 1 1 calc R U . . .
C26 C 0.9522(9) 0.0550(4) -0.0662(2) 0.0440(15) Uani 1 1 d . . . . .
H26A H 0.905134 0.083478 -0.102465 0.066 Uiso 1 1 calc R U . . .
H26B H 0.922846 0.000151 -0.072405 0.066 Uiso 1 1 calc R U . . .
H26C H 1.122210 0.063405 -0.058297 0.066 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
F1 C18 1.374(5) . ?
N1 C1 1.333(5) . ?
N1 N2 1.337(4) . ?
N2 N3 1.334(5) . ?
N2 C10 1.463(5) . ?
N3 C2 1.339(5) . ?
C1 C2 1.394(6) . ?
C1 H1A 0.9500 . ?
C2 C3 1.478(6) . ?
C3 C8 1.389(6) . ?
C3 C4 1.394(5) . ?
C4 C5 1.392(6) . ?
C4 H4A 0.9500 . ?
C5 C6 1.380(6) . ?
C5 H5A 0.9500 . ?
C6 C7 1.394(6) . ?
C6 C9 1.511(6) . ?
C7 C8 1.386(6) . ?
C7 H7A 0.9500 . ?
C8 H8A 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.513(7) . ?
C10 C18 1.512(6) . ?
C10 H10A 1.0000 . ?
C11 C12 1.370(7) . ?
C11 C16 1.385(6) . ?
C12 C13 1.403(7) . ?
C12 H12A 0.9500 . ?
C13 C14 1.383(6) . ?
C13 H13A 0.9500 . ?
C14 C15 1.384(6) . ?
C14 C17 1.498(7) . ?
C15 C16 1.393(7) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.304(6) . ?
C19 C20 1.477(6) . ?
C19 H19A 0.9500 . ?
C20 C21 1.377(6) . ?
C20 C25 1.386(7) . ?
C21 C22 1.384(6) . ?
C21 H21A 0.9500 . ?
C22 C23 1.385(7) . ?
C22 H22A 0.9500 . ?
C23 C24 1.381(6) . ?
C23 C26 1.506(6) . ?
C24 C25 1.389(6) . ?
C24 H24A 0.9500 . ?
C25 H25A 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?

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 N1 N2 103.1(4) . . ?
N3 N2 N1 115.7(4) . . ?
N3 N2 C10 121.3(3) . . ?
N1 N2 C10 122.7(4) . . ?
N2 N3 C2 103.3(3) . . ?
N1 C1 C2 109.2(4) . . ?
N1 C1 H1A 125.4 . . ?
C2 C1 H1A 125.4 . . ?
N3 C2 C1 108.6(4) . . ?
N3 C2 C3 121.2(4) . . ?
C1 C2 C3 130.1(4) . . ?
C8 C3 C4 118.7(4) . . ?
C8 C3 C2 121.1(4) . . ?
C4 C3 C2 120.2(4) . . ?
C5 C4 C3 120.3(4) . . ?
C5 C4 H4A 119.9 . . ?
C3 C4 H4A 119.9 . . ?
C6 C5 C4 121.4(4) . . ?
C6 C5 H5A 119.3 . . ?
C4 C5 H5A 119.3 . . ?
C5 C6 C7 117.9(4) . . ?
C5 C6 C9 121.2(4) . . ?
C7 C6 C9 120.8(4) . . ?
C8 C7 C6 121.4(4) . . ?
C8 C7 H7A 119.3 . . ?
C6 C7 H7A 119.3 . . ?
C7 C8 C3 120.3(4) . . ?
C7 C8 H8A 119.8 . . ?
C3 C8 H8A 119.8 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2 C10 C11 112.4(4) . . ?
N2 C10 C18 109.1(4) . . ?
C11 C10 C18 112.1(4) . . ?
N2 C10 H10A 107.7 . . ?
C11 C10 H10A 107.7 . . ?
C18 C10 H10A 107.7 . . ?
C12 C11 C16 119.1(5) . . ?
C12 C11 C10 121.7(4) . . ?
C16 C11 C10 119.2(5) . . ?
C11 C12 C13 120.6(4) . . ?
C11 C12 H12A 119.7 . . ?
C13 C12 H12A 119.7 . . ?
C14 C13 C12 120.4(5) . . ?
C14 C13 H13A 119.8 . . ?
C12 C13 H13A 119.8 . . ?
C15 C14 C13 118.7(5) . . ?
C15 C14 C17 119.9(5) . . ?
C13 C14 C17 121.4(5) . . ?
C14 C15 C16 120.6(4) . . ?
C14 C15 H15A 119.7 . . ?
C16 C15 H15A 119.7 . . ?
C11 C16 C15 120.5(5) . . ?
C11 C16 H16A 119.7 . . ?
C15 C16 H16A 119.7 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 F1 120.5(5) . . ?
C19 C18 C10 128.5(5) . . ?
F1 C18 C10 110.9(4) . . ?
C18 C19 C20 129.6(5) . . ?
C18 C19 H19A 115.2 . . ?
C20 C19 H19A 115.2 . . ?
C21 C20 C25 118.1(4) . . ?
C21 C20 C19 119.1(5) . . ?
C25 C20 C19 122.8(4) . . ?
C20 C21 C22 121.4(5) . . ?
C20 C21 H21A 119.3 . . ?
C22 C21 H21A 119.3 . . ?
C23 C22 C21 120.9(5) . . ?
C23 C22 H22A 119.6 . . ?
C21 C22 H22A 119.6 . . ?
C24 C23 C22 117.7(5) . . ?
C24 C23 C26 121.1(5) . . ?
C22 C23 C26 121.2(5) . . ?
C23 C24 C25 121.5(5) . . ?
C23 C24 H24A 119.3 . . ?
C25 C24 H24A 119.3 . . ?
C20 C25 C24 120.5(5) . . ?
C20 C25 H25A 119.8 . . ?
C24 C25 H25A 119.8 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

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
C1 N1 N2 N3 -0.4(6) . . . . ?
C1 N1 N2 C10 173.4(5) . . . . ?
N1 N2 N3 C2 -0.4(6) . . . . ?
C10 N2 N3 C2 -174.3(4) . . . . ?
N2 N1 C1 C2 1.0(6) . . . . ?
N2 N3 C2 C1 1.0(5) . . . . ?
N2 N3 C2 C3 -177.1(5) . . . . ?
N1 C1 C2 N3 -1.4(6) . . . . ?
N1 C1 C2 C3 176.5(5) . . . . ?
N3 C2 C3 C8 22.5(8) . . . . ?
C1 C2 C3 C8 -155.1(5) . . . . ?
N3 C2 C3 C4 -158.2(4) . . . . ?
C1 C2 C3 C4 24.2(9) . . . . ?
C8 C3 C4 C5 1.0(7) . . . . ?
C2 C3 C4 C5 -178.4(5) . . . . ?
C3 C4 C5 C6 0.4(8) . . . . ?
C4 C5 C6 C7 -1.1(8) . . . . ?
C4 C5 C6 C9 176.6(5) . . . . ?
C5 C6 C7 C8 0.5(8) . . . . ?
C9 C6 C7 C8 -177.2(5) . . . . ?
C6 C7 C8 C3 0.8(8) . . . . ?
C4 C3 C8 C7 -1.6(7) . . . . ?
C2 C3 C8 C7 177.8(5) . . . . ?
N3 N2 C10 C11 85.4(5) . . . . ?
N1 N2 C10 C11 -88.0(5) . . . . ?
N3 N2 C10 C18 -149.6(5) . . . . ?
N1 N2 C10 C18 37.0(7) . . . . ?
N2 C10 C11 C12 34.2(6) . . . . ?
C18 C10 C11 C12 -89.2(5) . . . . ?
N2 C10 C11 C16 -148.3(4) . . . . ?
C18 C10 C11 C16 88.3(5) . . . . ?
C16 C11 C12 C13 0.1(7) . . . . ?
C10 C11 C12 C13 177.5(4) . . . . ?
C11 C12 C13 C14 -0.5(7) . . . . ?
C12 C13 C14 C15 0.6(7) . . . . ?
C12 C13 C14 C17 -178.9(4) . . . . ?
C13 C14 C15 C16 -0.3(7) . . . . ?
C17 C14 C15 C16 179.2(4) . . . . ?
C12 C11 C16 C15 0.2(7) . . . . ?
C10 C11 C16 C15 -177.3(4) . . . . ?
C14 C15 C16 C11 -0.1(7) . . . . ?
N2 C10 C18 C19 -130.1(5) . . . . ?
C11 C10 C18 C19 -4.9(7) . . . . ?
N2 C10 C18 F1 53.7(5) . . . . ?
C11 C10 C18 F1 178.9(4) . . . . ?
F1 C18 C19 C20 -3.3(8) . . . . ?
C10 C18 C19 C20 -179.3(4) . . . . ?
C18 C19 C20 C21 155.7(5) . . . . ?
C18 C19 C20 C25 -28.2(8) . . . . ?
C25 C20 C21 C22 1.2(8) . . . . ?
C19 C20 C21 C22 177.5(5) . . . . ?
C20 C21 C22 C23 -1.5(8) . . . . ?
C21 C22 C23 C24 0.5(8) . . . . ?
C21 C22 C23 C26 -177.7(5) . . . . ?
C22 C23 C24 C25 0.7(9) . . . . ?
C26 C23 C24 C25 178.9(5) . . . . ?
C21 C20 C25 C24 0.0(8) . . . . ?
C19 C20 C25 C24 -176.1(5) . . . . ?
C23 C24 C25 C20 -1.0(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H1A N3 0.95 2.60 3.406(5) 142.6 1_655 yes

_refine_diff_density_max         0.242
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.052



####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2003624'
loop_
_audit_author_name
_audit_author_address
'Anand Singh'
;IIT Kanpur
India
;
_audit_update_record             
;
2020-05-12 deposited with the CCDC.	2020-10-30 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 H16 F N3'
_chemical_formula_sum            'C21 H16 F N3'
_chemical_formula_weight         329.37

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   9.2995(5)
_cell_length_b                   9.7287(5)
_cell_length_c                   37.4385(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3387.1(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8363
_cell_measurement_theta_min      3.09
_cell_measurement_theta_max      27.29

_exptl_crystal_description       prism
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_F_000             1376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6928
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            50211
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_av_R_equivalents  0.0791
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -49
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_theta_min         3.079
_diffrn_reflns_theta_max         28.220
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4168
_reflns_number_gt                2979
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_molecular_graphics    'Bruker SHELXTL (Sheldrick 2008)'
_computing_publication_material  'Bruker SHELXTL (Sheldrick 2008)'
_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)+(0.0285P)²+1.9177P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0026(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4168
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0440
_refine_ls_wR_factor_ref         0.1079
_refine_ls_wR_factor_gt          0.0892
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.001
_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
F1 F 0.19312(11) 0.83665(10) 0.32208(2) 0.0339(2) Uani 1 1 d . . . . .
N1 N 0.16948(13) 0.72337(12) 0.41328(3) 0.0211(3) Uani 1 1 d . . . . .
N2 N 0.18890(14) 0.59023(13) 0.42293(3) 0.0241(3) Uani 1 1 d . . . . .
N3 N 0.10521(15) 0.56250(13) 0.45003(3) 0.0258(3) Uani 1 1 d . . . . .
C1 C -0.01320(17) 0.60721(17) 0.31032(4) 0.0269(4) Uani 1 1 d . . . . .
C2 C -0.07926(19) 0.47816(19) 0.30960(5) 0.0332(4) Uani 1 1 d . . . . .
H2A H -0.070007 0.418255 0.329504 0.040 Uiso 1 1 calc R U . . .
C3 C -0.1580(2) 0.4370(2) 0.28014(5) 0.0426(5) Uani 1 1 d . . . . .
H3A H -0.201727 0.348786 0.279834 0.051 Uiso 1 1 calc R U . . .
C4 C -0.1732(2) 0.5239(2) 0.25108(5) 0.0459(5) Uani 1 1 d . . . . .
H4A H -0.228914 0.496231 0.231062 0.055 Uiso 1 1 calc R U . . .
C5 C -0.1072(2) 0.6509(2) 0.25133(5) 0.0449(5) Uani 1 1 d . . . . .
H5A H -0.116368 0.709915 0.231241 0.054 Uiso 1 1 calc R U . . .
C6 C -0.0276(2) 0.69322(19) 0.28060(4) 0.0347(4) Uani 1 1 d . . . . .
H6A H 0.017334 0.780916 0.280493 0.042 Uiso 1 1 calc R U . . .
C7 C 0.06580(17) 0.64510(16) 0.34286(4) 0.0247(3) Uani 1 1 d . . . . .
H7A H 0.049114 0.587029 0.362837 0.030 Uiso 1 1 calc R U . . .
C8 C 0.15611(17) 0.74698(16) 0.34867(4) 0.0231(3) Uani 1 1 d . . . . .
C9 C 0.24098(17) 0.77926(15) 0.38167(4) 0.0219(3) Uani 1 1 d . . . . .
H9A H 0.242366 0.881538 0.384295 0.026 Uiso 1 1 calc R U . . .
C10 C 0.06749(16) 0.78324(15) 0.43458(4) 0.0211(3) Uani 1 1 d . . . . .
C11 C 0.00702(18) 0.91479(16) 0.43586(4) 0.0263(3) Uani 1 1 d . . . . .
H11A H 0.033034 0.984986 0.419447 0.032 Uiso 1 1 calc R U . . .
C12 C -0.09256(19) 0.93577(18) 0.46244(5) 0.0324(4) Uani 1 1 d . . . . .
H12A H -0.136789 1.023464 0.464421 0.039 Uiso 1 1 calc R U . . .
C13 C -0.13142(19) 0.83215(19) 0.48684(4) 0.0347(4) Uani 1 1 d . . . . .
H13A H -0.199932 0.852352 0.504913 0.042 Uiso 1 1 calc R U . . .
C14 C -0.07324(18) 0.70310(18) 0.48523(4) 0.0303(4) Uani 1 1 d . . . . .
H14A H -0.100256 0.633174 0.501625 0.036 Uiso 1 1 calc R U . . .
C15 C 0.02818(17) 0.67906(15) 0.45823(4) 0.0232(3) Uani 1 1 d . . . . .
C16 C 0.39671(17) 0.73162(15) 0.37927(4) 0.0232(3) Uani 1 1 d . . . . .
C17 C 0.49588(18) 0.77983(17) 0.40414(4) 0.0279(4) Uani 1 1 d . . . . .
H17A H 0.465408 0.839756 0.422689 0.034 Uiso 1 1 calc R U . . .
C18 C 0.63854(19) 0.74084(19) 0.40195(5) 0.0363(4) Uani 1 1 d . . . . .
H18A H 0.705890 0.774185 0.418947 0.044 Uiso 1 1 calc R U . . .
C19 C 0.6834(2) 0.6533(2) 0.37504(5) 0.0425(5) Uani 1 1 d . . . . .
H19A H 0.781569 0.626969 0.373481 0.051 Uiso 1 1 calc R U . . .
C20 C 0.5853(2) 0.6043(2) 0.35044(5) 0.0397(5) Uani 1 1 d . . . . .
H20A H 0.616052 0.543604 0.332083 0.048 Uiso 1 1 calc R U . . .
C21 C 0.44242(18) 0.64337(18) 0.35243(4) 0.0298(4) Uani 1 1 d . . . . .
H21A H 0.375431 0.609699 0.335392 0.036 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
F1 C8 1.3676(17) . ?
N1 N2 1.3568(17) . ?
N1 C10 1.3692(19) . ?
N1 C9 1.4623(18) . ?
N2 N3 1.3070(18) . ?
N3 C15 1.376(2) . ?
C1 C2 1.398(2) . ?
C1 C6 1.399(2) . ?
C1 C7 1.470(2) . ?
C2 C3 1.383(2) . ?
C2 H2A 0.9500 . ?
C3 C4 1.385(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.380(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.385(3) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 C8 1.317(2) . ?
C7 H7A 0.9500 . ?
C8 C9 1.499(2) . ?
C9 C16 1.523(2) . ?
C9 H9A 1.0000 . ?
C10 C15 1.395(2) . ?
C10 C11 1.399(2) . ?
C11 C12 1.375(2) . ?
C11 H11A 0.9500 . ?
C12 C13 1.407(2) . ?
C12 H12A 0.9500 . ?
C13 C14 1.368(2) . ?
C13 H13A 0.9500 . ?
C14 C15 1.402(2) . ?
C14 H14A 0.9500 . ?
C16 C21 1.388(2) . ?
C16 C17 1.392(2) . ?
C17 C18 1.382(2) . ?
C17 H17A 0.9500 . ?
C18 C19 1.383(3) . ?
C18 H18A 0.9500 . ?
C19 C20 1.381(3) . ?
C19 H19A 0.9500 . ?
C20 C21 1.384(2) . ?
C20 H20A 0.9500 . ?
C21 H21A 0.9500 . ?

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
N2 N1 C10 110.08(12) . . ?
N2 N1 C9 120.66(12) . . ?
C10 N1 C9 128.91(13) . . ?
N3 N2 N1 108.94(12) . . ?
N2 N3 C15 108.24(12) . . ?
C2 C1 C6 118.68(16) . . ?
C2 C1 C7 117.45(15) . . ?
C6 C1 C7 123.87(16) . . ?
C3 C2 C1 120.53(18) . . ?
C3 C2 H2A 119.7 . . ?
C1 C2 H2A 119.7 . . ?
C2 C3 C4 120.26(19) . . ?
C2 C3 H3A 119.9 . . ?
C4 C3 H3A 119.9 . . ?
C5 C4 C3 119.70(18) . . ?
C5 C4 H4A 120.1 . . ?
C3 C4 H4A 120.1 . . ?
C4 C5 C6 120.63(19) . . ?
C4 C5 H5A 119.7 . . ?
C6 C5 H5A 119.7 . . ?
C5 C6 C1 120.19(18) . . ?
C5 C6 H6A 119.9 . . ?
C1 C6 H6A 119.9 . . ?
C8 C7 C1 130.11(15) . . ?
C8 C7 H7A 114.9 . . ?
C1 C7 H7A 114.9 . . ?
C7 C8 F1 121.35(14) . . ?
C7 C8 C9 129.00(14) . . ?
F1 C8 C9 109.50(12) . . ?
N1 C9 C8 110.47(13) . . ?
N1 C9 C16 111.52(12) . . ?
C8 C9 C16 112.85(12) . . ?
N1 C9 H9A 107.2 . . ?
C8 C9 H9A 107.2 . . ?
C16 C9 H9A 107.2 . . ?
N1 C10 C15 104.01(13) . . ?
N1 C10 C11 133.45(14) . . ?
C15 C10 C11 122.53(14) . . ?
C12 C11 C10 115.57(15) . . ?
C12 C11 H11A 122.2 . . ?
C10 C11 H11A 122.2 . . ?
C11 C12 C13 122.44(16) . . ?
C11 C12 H12A 118.8 . . ?
C13 C12 H12A 118.8 . . ?
C14 C13 C12 121.81(15) . . ?
C14 C13 H13A 119.1 . . ?
C12 C13 H13A 119.1 . . ?
C13 C14 C15 116.78(15) . . ?
C13 C14 H14A 121.6 . . ?
C15 C14 H14A 121.6 . . ?
N3 C15 C10 108.72(13) . . ?
N3 C15 C14 130.42(14) . . ?
C10 C15 C14 120.85(15) . . ?
C21 C16 C17 119.32(15) . . ?
C21 C16 C9 121.45(14) . . ?
C17 C16 C9 119.22(14) . . ?
C18 C17 C16 120.25(16) . . ?
C18 C17 H17A 119.9 . . ?
C16 C17 H17A 119.9 . . ?
C17 C18 C19 120.10(17) . . ?
C17 C18 H18A 120.0 . . ?
C19 C18 H18A 120.0 . . ?
C20 C19 C18 119.94(17) . . ?
C20 C19 H19A 120.0 . . ?
C18 C19 H19A 120.0 . . ?
C19 C20 C21 120.21(17) . . ?
C19 C20 H20A 119.9 . . ?
C21 C20 H20A 119.9 . . ?
C20 C21 C16 120.19(16) . . ?
C20 C21 H21A 119.9 . . ?
C16 C21 H21A 119.9 . . ?

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
C10 N1 N2 N3 -1.09(16) . . . . ?
C9 N1 N2 N3 -174.86(13) . . . . ?
N1 N2 N3 C15 0.55(16) . . . . ?
C6 C1 C2 C3 -0.4(3) . . . . ?
C7 C1 C2 C3 178.60(16) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
C2 C3 C4 C5 1.3(3) . . . . ?
C3 C4 C5 C6 -1.0(3) . . . . ?
C4 C5 C6 C1 0.1(3) . . . . ?
C2 C1 C6 C5 0.6(3) . . . . ?
C7 C1 C6 C5 -178.29(16) . . . . ?
C2 C1 C7 C8 167.33(17) . . . . ?
C6 C1 C7 C8 -13.7(3) . . . . ?
C1 C7 C8 F1 -1.7(3) . . . . ?
C1 C7 C8 C9 -176.62(16) . . . . ?
N2 N1 C9 C8 83.67(16) . . . . ?
C10 N1 C9 C8 -88.80(18) . . . . ?
N2 N1 C9 C16 -42.68(18) . . . . ?
C10 N1 C9 C16 144.86(15) . . . . ?
C7 C8 C9 N1 -25.7(2) . . . . ?
F1 C8 C9 N1 158.91(12) . . . . ?
C7 C8 C9 C16 99.91(19) . . . . ?
F1 C8 C9 C16 -75.49(15) . . . . ?
N2 N1 C10 C15 1.14(16) . . . . ?
C9 N1 C10 C15 174.24(14) . . . . ?
N2 N1 C10 C11 -179.27(17) . . . . ?
C9 N1 C10 C11 -6.2(3) . . . . ?
N1 C10 C11 C12 -178.50(16) . . . . ?
C15 C10 C11 C12 1.0(2) . . . . ?
C10 C11 C12 C13 0.0(2) . . . . ?
C11 C12 C13 C14 -0.8(3) . . . . ?
C12 C13 C14 C15 0.5(3) . . . . ?
N2 N3 C15 C10 0.17(17) . . . . ?
N2 N3 C15 C14 -178.79(16) . . . . ?
N1 C10 C15 N3 -0.79(16) . . . . ?
C11 C10 C15 N3 179.56(14) . . . . ?
N1 C10 C15 C14 178.28(14) . . . . ?
C11 C10 C15 C14 -1.4(2) . . . . ?
C13 C14 C15 N3 179.40(16) . . . . ?
C13 C14 C15 C10 0.6(2) . . . . ?
N1 C9 C16 C21 112.50(16) . . . . ?
C8 C9 C16 C21 -12.5(2) . . . . ?
N1 C9 C16 C17 -68.78(18) . . . . ?
C8 C9 C16 C17 166.18(14) . . . . ?
C21 C16 C17 C18 0.4(2) . . . . ?
C9 C16 C17 C18 -178.32(15) . . . . ?
C16 C17 C18 C19 -0.2(3) . . . . ?
C17 C18 C19 C20 -0.3(3) . . . . ?
C18 C19 C20 C21 0.5(3) . . . . ?
C19 C20 C21 C16 -0.3(3) . . . . ?
C17 C16 C21 C20 -0.2(3) . . . . ?
C9 C16 C21 C20 178.50(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C7 H7A N2 0.95 2.60 3.253(2) 126.3 . yes
C9 H9A N2 1.00 2.57 3.459(2) 147.5 8_665 yes
C14 H14A N3 0.95 2.63 3.555(2) 165.6 5_566 yes

_refine_diff_density_max         0.250
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.047



####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2003625'
loop_
_audit_author_name
_audit_author_address
'Anand Singh'
;IIT Kanpur
India
;
_audit_update_record             
;
2020-05-12 deposited with the CCDC.	2020-10-30 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 H20 F N3 O'
_chemical_formula_sum            'C24 H20 F N3 O'
_chemical_formula_weight         385.43

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'
O O 0.0106 0.0060 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   5.4142(7)
_cell_length_b                   20.890(3)
_cell_length_c                   8.3858(11)
_cell_angle_alpha                90
_cell_angle_beta                 92.126(4)
_cell_angle_gamma                90
_cell_volume                     947.8(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3553
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      25.94

_exptl_crystal_description       plate
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_F_000             404
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4135
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14841
_diffrn_reflns_av_unetI/netI     0.1138
_diffrn_reflns_av_R_equivalents  0.1112
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.117
_diffrn_reflns_theta_max         28.306
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4653
_reflns_number_gt                3615
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.939
_reflns_Friedel_fraction_max     0.982
_reflns_Friedel_fraction_full    0.999

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_molecular_graphics    'Bruker SHELXTL (Sheldrick 2008)'
_computing_publication_material  'Bruker SHELXTL (Sheldrick 2008)'
_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)+(0.0474P)²+0.1798P] 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_abs_structure_details 
;
 Flack x determined using 1183 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.2(10)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         4653
_refine_ls_number_parameters     263
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0936
_refine_ls_R_factor_gt           0.0692
_refine_ls_wR_factor_ref         0.1570
_refine_ls_wR_factor_gt          0.1444
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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
F1 F 0.6614(5) 0.62863(13) 0.4370(3) 0.0280(7) Uani 1 1 d . . . . .
O1 O 0.5129(7) 0.16582(15) 0.9250(4) 0.0293(8) Uani 1 1 d . . . . .
N1 N 0.7868(6) 0.49799(18) 0.5702(5) 0.0187(8) Uani 1 1 d . . . . .
N2 N 0.5580(7) 0.51274(19) 0.6146(5) 0.0266(9) Uani 1 1 d . . . . .
N3 N 0.4682(7) 0.46078(19) 0.6804(5) 0.0271(9) Uani 1 1 d . . . . .
C1 C 0.9582(8) 0.7198(2) 0.6382(5) 0.0210(10) Uani 1 1 d . . . . .
C2 C 1.1262(8) 0.7505(2) 0.7428(6) 0.0255(10) Uani 1 1 d . . . . .
H2A H 1.267172 0.727757 0.782805 0.031 Uiso 1 1 calc R U . . .
C3 C 1.0922(9) 0.8139(2) 0.7901(6) 0.0269(11) Uani 1 1 d . . . . .
H3A H 1.209437 0.834036 0.860671 0.032 Uiso 1 1 calc R U . . .
C4 C 0.8838(8) 0.8475(2) 0.7325(6) 0.0250(10) Uani 1 1 d . . . . .
H4A H 0.856534 0.890388 0.765120 0.030 Uiso 1 1 calc R U . . .
C5 C 0.7178(9) 0.8175(2) 0.6274(6) 0.0241(10) Uani 1 1 d . . . . .
H5A H 0.578182 0.840450 0.586116 0.029 Uiso 1 1 calc R U . . .
C6 C 0.7522(8) 0.7542(2) 0.5815(6) 0.0240(10) Uani 1 1 d . . . . .
H6A H 0.634401 0.734316 0.510915 0.029 Uiso 1 1 calc R U . . .
C7 C 1.0072(8) 0.6524(2) 0.6015(6) 0.0206(10) Uani 1 1 d . . . . .
H7A H 1.157121 0.635716 0.646967 0.025 Uiso 1 1 calc R U . . .
C8 C 0.8741(8) 0.6116(2) 0.5148(5) 0.0187(9) Uani 1 1 d . . . . .
C9 C 0.9460(8) 0.5430(2) 0.4865(6) 0.0192(9) Uani 1 1 d . . . . .
H9A H 1.117927 0.537304 0.532000 0.023 Uiso 1 1 calc R U . . .
C10 C 0.8418(8) 0.4364(2) 0.6038(6) 0.0205(10) Uani 1 1 d . . . . .
H10A H 0.990098 0.414183 0.582609 0.025 Uiso 1 1 calc R U . . .
C11 C 0.6377(8) 0.4130(2) 0.6751(5) 0.0188(9) Uani 1 1 d . . . . .
C12 C 0.5975(8) 0.3492(2) 0.7415(5) 0.0191(9) Uani 1 1 d . . . . .
C13 C 0.7581(8) 0.2989(2) 0.7056(6) 0.0218(10) Uani 1 1 d . . . . .
H13A H 0.890631 0.306211 0.636744 0.026 Uiso 1 1 calc R U . . .
C14 C 0.7245(8) 0.2386(2) 0.7697(6) 0.0254(11) Uani 1 1 d . . . . .
H14A H 0.835608 0.204958 0.746418 0.030 Uiso 1 1 calc R U . . .
C15 C 0.5292(8) 0.2274(2) 0.8676(5) 0.0219(10) Uani 1 1 d . . . . .
C16 C 0.3686(8) 0.2759(2) 0.9035(6) 0.0235(10) Uani 1 1 d . . . . .
H16A H 0.234564 0.267843 0.970639 0.028 Uiso 1 1 calc R U . . .
C17 C 0.4034(8) 0.3367(2) 0.8411(6) 0.0237(10) Uani 1 1 d . . . . .
H17A H 0.293001 0.370162 0.866824 0.028 Uiso 1 1 calc R U . . .
C18 C 0.3132(10) 0.1515(3) 1.0253(7) 0.0352(13) Uani 1 1 d . . . . .
H18A H 0.324286 0.106743 1.059620 0.053 Uiso 1 1 calc R U . . .
H18B H 0.155994 0.158498 0.966109 0.053 Uiso 1 1 calc R U . . .
H18C H 0.321922 0.179519 1.119134 0.053 Uiso 1 1 calc R U . . .
C19 C 0.9510(8) 0.5266(2) 0.3076(6) 0.0199(9) Uani 1 1 d . . . . .
C20 C 1.1520(8) 0.5467(2) 0.2247(6) 0.0247(10) Uani 1 1 d . . . . .
H20A H 1.278405 0.571080 0.277628 0.030 Uiso 1 1 calc R U . . .
C21 C 1.1708(9) 0.5315(2) 0.0642(6) 0.0286(11) Uani 1 1 d . . . . .
H21A H 1.307873 0.546116 0.006731 0.034 Uiso 1 1 calc R U . . .
C22 C 0.9886(9) 0.4952(2) -0.0107(6) 0.0283(11) Uani 1 1 d . . . . .
H22A H 1.002422 0.483526 -0.119520 0.034 Uiso 1 1 calc R U . . .
C23 C 0.7862(9) 0.4756(2) 0.0718(6) 0.0267(11) Uani 1 1 d . . . . .
H23A H 0.659811 0.451234 0.018602 0.032 Uiso 1 1 calc R U . . .
C24 C 0.7656(8) 0.4909(2) 0.2307(6) 0.0239(10) Uani 1 1 d . . . . .
H24A H 0.625922 0.477250 0.286999 0.029 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
F1 C8 1.350(5) . ?
O1 C15 1.377(6) . ?
O1 C18 1.426(5) . ?
N1 N2 1.343(5) . ?
N1 C10 1.348(6) . ?
N1 C9 1.471(6) . ?
N2 N3 1.319(5) . ?
N3 C11 1.358(6) . ?
C1 C6 1.396(7) . ?
C1 C2 1.396(7) . ?
C1 C7 1.467(6) . ?
C2 C3 1.396(7) . ?
C2 H2A 0.9500 . ?
C3 C4 1.399(7) . ?
C3 H3A 0.9500 . ?
C4 C5 1.385(7) . ?
C4 H4A 0.9500 . ?
C5 C6 1.390(7) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 C8 1.317(6) . ?
C7 H7A 0.9500 . ?
C8 C9 1.505(6) . ?
C9 C19 1.540(7) . ?
C9 H9A 1.0000 . ?
C10 C11 1.367(6) . ?
C10 H10A 0.9500 . ?
C11 C12 1.463(6) . ?
C12 C17 1.392(6) . ?
C12 C13 1.405(6) . ?
C13 C14 1.383(7) . ?
C13 H13A 0.9500 . ?
C14 C15 1.383(6) . ?
C14 H14A 0.9500 . ?
C15 C16 1.376(6) . ?
C16 C17 1.389(6) . ?
C16 H16A 0.9500 . ?
C17 H17A 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.378(6) . ?
C19 C24 1.389(6) . ?
C20 C21 1.390(7) . ?
C20 H20A 0.9500 . ?
C21 C22 1.378(7) . ?
C21 H21A 0.9500 . ?
C22 C23 1.379(7) . ?
C22 H22A 0.9500 . ?
C23 C24 1.379(7) . ?
C23 H23A 0.9500 . ?
C24 H24A 0.9500 . ?

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
C15 O1 C18 117.5(4) . . ?
N2 N1 C10 111.1(4) . . ?
N2 N1 C9 123.3(4) . . ?
C10 N1 C9 125.5(4) . . ?
N3 N2 N1 106.6(4) . . ?
N2 N3 C11 109.4(4) . . ?
C6 C1 C2 118.0(4) . . ?
C6 C1 C7 124.9(4) . . ?
C2 C1 C7 117.0(4) . . ?
C3 C2 C1 121.7(5) . . ?
C3 C2 H2A 119.2 . . ?
C1 C2 H2A 119.2 . . ?
C2 C3 C4 119.4(5) . . ?
C2 C3 H3A 120.3 . . ?
C4 C3 H3A 120.3 . . ?
C5 C4 C3 119.2(5) . . ?
C5 C4 H4A 120.4 . . ?
C3 C4 H4A 120.4 . . ?
C4 C5 C6 121.1(5) . . ?
C4 C5 H5A 119.5 . . ?
C6 C5 H5A 119.5 . . ?
C5 C6 C1 120.6(5) . . ?
C5 C6 H6A 119.7 . . ?
C1 C6 H6A 119.7 . . ?
C8 C7 C1 129.6(4) . . ?
C8 C7 H7A 115.2 . . ?
C1 C7 H7A 115.2 . . ?
C7 C8 F1 122.3(4) . . ?
C7 C8 C9 124.3(4) . . ?
F1 C8 C9 113.3(4) . . ?
N1 C9 C8 111.9(3) . . ?
N1 C9 C19 110.7(4) . . ?
C8 C9 C19 112.3(4) . . ?
N1 C9 H9A 107.2 . . ?
C8 C9 H9A 107.2 . . ?
C19 C9 H9A 107.2 . . ?
N1 C10 C11 104.9(4) . . ?
N1 C10 H10A 127.5 . . ?
C11 C10 H10A 127.5 . . ?
N3 C11 C10 108.0(4) . . ?
N3 C11 C12 123.2(4) . . ?
C10 C11 C12 128.8(4) . . ?
C17 C12 C13 118.3(4) . . ?
C17 C12 C11 121.7(4) . . ?
C13 C12 C11 119.9(4) . . ?
C14 C13 C12 120.5(4) . . ?
C14 C13 H13A 119.8 . . ?
C12 C13 H13A 119.8 . . ?
C13 C14 C15 120.0(4) . . ?
C13 C14 H14A 120.0 . . ?
C15 C14 H14A 120.0 . . ?
C16 C15 O1 124.2(4) . . ?
C16 C15 C14 120.5(4) . . ?
O1 C15 C14 115.3(4) . . ?
C15 C16 C17 119.7(4) . . ?
C15 C16 H16A 120.1 . . ?
C17 C16 H16A 120.1 . . ?
C16 C17 C12 120.9(4) . . ?
C16 C17 H17A 119.5 . . ?
C12 C17 H17A 119.5 . . ?
O1 C18 H18A 109.5 . . ?
O1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C24 120.0(4) . . ?
C20 C19 C9 117.8(4) . . ?
C24 C19 C9 122.2(4) . . ?
C19 C20 C21 120.4(5) . . ?
C19 C20 H20A 119.8 . . ?
C21 C20 H20A 119.8 . . ?
C22 C21 C20 119.3(5) . . ?
C22 C21 H21A 120.3 . . ?
C20 C21 H21A 120.3 . . ?
C21 C22 C23 120.2(5) . . ?
C21 C22 H22A 119.9 . . ?
C23 C22 H22A 119.9 . . ?
C24 C23 C22 120.6(5) . . ?
C24 C23 H23A 119.7 . . ?
C22 C23 H23A 119.7 . . ?
C23 C24 C19 119.4(4) . . ?
C23 C24 H24A 120.3 . . ?
C19 C24 H24A 120.3 . . ?

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
C10 N1 N2 N3 1.5(5) . . . . ?
C9 N1 N2 N3 177.7(4) . . . . ?
N1 N2 N3 C11 -1.1(5) . . . . ?
C6 C1 C2 C3 -0.2(7) . . . . ?
C7 C1 C2 C3 -177.7(4) . . . . ?
C1 C2 C3 C4 0.5(7) . . . . ?
C2 C3 C4 C5 -1.2(7) . . . . ?
C3 C4 C5 C6 1.5(7) . . . . ?
C4 C5 C6 C1 -1.2(7) . . . . ?
C2 C1 C6 C5 0.5(6) . . . . ?
C7 C1 C6 C5 177.8(4) . . . . ?
C6 C1 C7 C8 -1.3(8) . . . . ?
C2 C1 C7 C8 176.0(5) . . . . ?
C1 C7 C8 F1 2.7(8) . . . . ?
C1 C7 C8 C9 -179.9(4) . . . . ?
N2 N1 C9 C8 23.1(6) . . . . ?
C10 N1 C9 C8 -161.2(4) . . . . ?
N2 N1 C9 C19 -103.0(5) . . . . ?
C10 N1 C9 C19 72.7(6) . . . . ?
C7 C8 C9 N1 109.7(5) . . . . ?
F1 C8 C9 N1 -72.7(5) . . . . ?
C7 C8 C9 C19 -125.0(5) . . . . ?
F1 C8 C9 C19 52.6(5) . . . . ?
N2 N1 C10 C11 -1.2(5) . . . . ?
C9 N1 C10 C11 -177.4(4) . . . . ?
N2 N3 C11 C10 0.4(5) . . . . ?
N2 N3 C11 C12 178.7(4) . . . . ?
N1 C10 C11 N3 0.5(5) . . . . ?
N1 C10 C11 C12 -177.7(4) . . . . ?
N3 C11 C12 C17 -12.5(7) . . . . ?
C10 C11 C12 C17 165.5(5) . . . . ?
N3 C11 C12 C13 167.8(4) . . . . ?
C10 C11 C12 C13 -14.2(7) . . . . ?
C17 C12 C13 C14 -0.8(7) . . . . ?
C11 C12 C13 C14 178.9(5) . . . . ?
C12 C13 C14 C15 1.1(7) . . . . ?
C18 O1 C15 C16 1.4(7) . . . . ?
C18 O1 C15 C14 -179.4(4) . . . . ?
C13 C14 C15 C16 -0.7(7) . . . . ?
C13 C14 C15 O1 -180.0(4) . . . . ?
O1 C15 C16 C17 179.1(5) . . . . ?
C14 C15 C16 C17 -0.2(7) . . . . ?
C15 C16 C17 C12 0.5(7) . . . . ?
C13 C12 C17 C16 -0.1(7) . . . . ?
C11 C12 C17 C16 -179.8(4) . . . . ?
N1 C9 C19 C20 -156.3(4) . . . . ?
C8 C9 C19 C20 77.7(5) . . . . ?
N1 C9 C19 C24 21.6(6) . . . . ?
C8 C9 C19 C24 -104.4(5) . . . . ?
C24 C19 C20 C21 0.0(7) . . . . ?
C9 C19 C20 C21 177.9(4) . . . . ?
C19 C20 C21 C22 -1.2(7) . . . . ?
C20 C21 C22 C23 1.8(8) . . . . ?
C21 C22 C23 C24 -1.3(7) . . . . ?
C22 C23 C24 C19 0.1(7) . . . . ?
C20 C19 C24 C23 0.6(7) . . . . ?
C9 C19 C24 C23 -177.3(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C9 H9A N2 1.00 2.51 3.503(6) 172.1 1_655 yes

_refine_diff_density_max         0.534
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.060



