# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_6a
_database_code_depnum_ccdc_archive 'CCDC 2349834'
loop_
_audit_author_name
_audit_author_address
'Tarun Kanti Panda'
;IIT Hyderabad
India
;
_audit_update_record             
;
2024-04-21 deposited with the CCDC.	2024-11-01 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         'C17 H15 F3 N2 O'
_chemical_formula_sum            'C17 H15 F3 N2 O'
_chemical_formula_weight         320.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_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                   5.2957(3)
_cell_length_b                   16.3601(12)
_cell_length_c                   18.4809(13)
_cell_angle_alpha                90
_cell_angle_beta                 94.244(2)
_cell_angle_gamma                90
_cell_volume                     1596.76(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    139(2)
_cell_measurement_reflns_used    25874
_cell_measurement_theta_min      2.490
_cell_measurement_theta_max      27.184

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_exptl_absorpt_coefficient_mu    0.108
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      139(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            25874
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.490
_diffrn_reflns_theta_max         27.184
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3538
_reflns_number_gt                2590
_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       'SAINT V8.38A (Bruker, 2018)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'ORTEP III and WINGX'
_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)+(0.0674P)²+0.5569P] 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         3538
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0559
_refine_ls_wR_factor_ref         0.1588
_refine_ls_wR_factor_gt          0.1432
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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
O1 O -0.1203(3) 0.00356(10) 0.37050(9) 0.0788(5) Uani 1 1 d . . . . .
F1 F 0.5580(6) 0.47777(13) 0.34942(13) 0.1892(15) Uani 1 1 d . . . . .
F2 F 0.9444(5) 0.46540(16) 0.37465(17) 0.1850(13) Uani 1 1 d . . . . .
F3 F 0.7289(5) 0.51886(10) 0.44834(12) 0.1324(8) Uani 1 1 d . . . . .
N1 N 0.4951(3) 0.26726(9) 0.45626(8) 0.0489(4) Uani 1 1 d . . . . .
N2 N 0.4928(3) 0.33560(9) 0.41441(8) 0.0519(4) Uani 1 1 d . . . . .
C1 C 0.6859(4) 0.37895(12) 0.43427(10) 0.0538(5) Uani 1 1 d . . . . .
C2 C 0.7220(6) 0.45930(16) 0.40039(15) 0.0850(8) Uani 1 1 d . . . . .
C3 C 0.8555(4) 0.34353(12) 0.49404(11) 0.0547(5) Uani 1 1 d . . . . .
H3A H 0.856972 0.377303 0.538515 0.066 Uiso 1 1 calc R U . . .
H3B H 1.030886 0.337417 0.479596 0.066 Uiso 1 1 calc R U . . .
C4 C 0.7300(3) 0.25951(11) 0.50483(10) 0.0462(4) Uani 1 1 d . . . . .
H4 H 0.838876 0.215240 0.486566 0.055 Uiso 1 1 calc R U . . .
C5 C 0.6819(3) 0.24304(11) 0.58272(9) 0.0456(4) Uani 1 1 d . . . . .
C6 C 0.8283(4) 0.18643(13) 0.62252(11) 0.0606(5) Uani 1 1 d . . . . .
H6 H 0.954496 0.156337 0.600033 0.073 Uiso 1 1 calc R U . . .
C7 C 0.7914(5) 0.17354(17) 0.69514(13) 0.0788(7) Uani 1 1 d . . . . .
H7 H 0.893538 0.134888 0.722178 0.095 Uiso 1 1 calc R U . . .
C8 C 0.6099(5) 0.21575(18) 0.72816(13) 0.0813(7) Uani 1 1 d . . . . .
H8 H 0.585918 0.206589 0.777946 0.098 Uiso 1 1 calc R U . . .
C9 C 0.4630(5) 0.27119(18) 0.68933(13) 0.0816(7) Uani 1 1 d . . . . .
H9 H 0.335668 0.300337 0.712175 0.098 Uiso 1 1 calc R U . . .
C10 C 0.4981(4) 0.28539(15) 0.61663(12) 0.0661(6) Uani 1 1 d . . . . .
H10 H 0.395338 0.324347 0.590127 0.079 Uiso 1 1 calc R U . . .
C11 C 0.3437(3) 0.20041(11) 0.43141(9) 0.0441(4) Uani 1 1 d . . . . .
C12 C 0.3606(4) 0.12626(12) 0.46777(10) 0.0531(5) Uani 1 1 d . . . . .
H12 H 0.480330 0.119524 0.508220 0.064 Uiso 1 1 calc R U . . .
C13 C 0.2041(4) 0.06212(12) 0.44540(11) 0.0589(5) Uani 1 1 d . . . . .
H13 H 0.217666 0.011544 0.470642 0.071 Uiso 1 1 calc R U . . .
C14 C 0.0285(4) 0.07042(12) 0.38705(11) 0.0550(5) Uani 1 1 d . . . . .
C15 C 0.0116(4) 0.14402(12) 0.35034(10) 0.0542(5) Uani 1 1 d . . . . .
H15 H -0.108590 0.150438 0.309966 0.065 Uiso 1 1 calc R U . . .
C16 C 0.1689(3) 0.20848(12) 0.37210(10) 0.0495(4) Uani 1 1 d . . . . .
H16 H 0.157020 0.258659 0.346202 0.059 Uiso 1 1 calc R U . . .
C17 C -0.3035(5) 0.00984(18) 0.31072(16) 0.0938(9) Uani 1 1 d . . . . .
H17A H -0.421436 0.054329 0.319423 0.141 Uiso 1 1 calc R U . . .
H17B H -0.397185 -0.041703 0.304987 0.141 Uiso 1 1 calc R U . . .
H17C H -0.218530 0.021221 0.266477 0.141 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
O1 C14 1.369(2) . ?
O1 C17 1.419(3) . ?
F1 C2 1.269(3) . ?
F2 C2 1.306(4) . ?
F3 C2 1.316(3) . ?
N1 N2 1.359(2) . ?
N1 C11 1.412(2) . ?
N1 C4 1.485(2) . ?
N2 C1 1.276(2) . ?
C1 C2 1.474(3) . ?
C1 C3 1.489(3) . ?
C3 C4 1.546(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.505(2) . ?
C4 H4 1.0000 . ?
C5 C10 1.382(3) . ?
C5 C6 1.384(3) . ?
C6 C7 1.387(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.364(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.364(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.389(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.387(3) . ?
C11 C16 1.388(2) . ?
C12 C13 1.382(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.377(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.382(3) . ?
C15 C16 1.385(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 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
C14 O1 C17 117.72(18) . . ?
N2 N1 C11 118.11(14) . . ?
N2 N1 C4 112.71(14) . . ?
C11 N1 C4 124.09(14) . . ?
C1 N2 N1 108.70(15) . . ?
N2 C1 C2 119.99(19) . . ?
N2 C1 C3 115.08(17) . . ?
C2 C1 C3 124.89(18) . . ?
F1 C2 F2 107.3(3) . . ?
F1 C2 F3 107.9(3) . . ?
F2 C2 F3 102.0(2) . . ?
F1 C2 C1 115.1(2) . . ?
F2 C2 C1 111.8(3) . . ?
F3 C2 C1 111.9(2) . . ?
C1 C3 C4 101.54(14) . . ?
C1 C3 H3A 111.5 . . ?
C4 C3 H3A 111.5 . . ?
C1 C3 H3B 111.5 . . ?
C4 C3 H3B 111.5 . . ?
H3A C3 H3B 109.3 . . ?
N1 C4 C5 113.59(14) . . ?
N1 C4 C3 101.25(14) . . ?
C5 C4 C3 112.80(15) . . ?
N1 C4 H4 109.6 . . ?
C5 C4 H4 109.6 . . ?
C3 C4 H4 109.6 . . ?
C10 C5 C6 118.70(19) . . ?
C10 C5 C4 121.24(17) . . ?
C6 C5 C4 120.02(17) . . ?
C5 C6 C7 120.1(2) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 120.7(2) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C9 119.6(2) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C8 C9 C10 120.5(2) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C5 C10 C9 120.2(2) . . ?
C5 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C12 C11 C16 118.78(16) . . ?
C12 C11 N1 120.34(16) . . ?
C16 C11 N1 120.83(16) . . ?
C13 C12 C11 120.24(18) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C14 C13 C12 120.99(19) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
O1 C14 C13 116.11(18) . . ?
O1 C14 C15 124.82(18) . . ?
C13 C14 C15 119.07(17) . . ?
C14 C15 C16 120.34(17) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C11 120.58(18) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
O1 C17 H17A 109.5 . . ?
O1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
C11 N1 N2 C1 -162.41(16) . . . . ?
C4 N1 N2 C1 -6.6(2) . . . . ?
N1 N2 C1 C2 -176.5(2) . . . . ?
N1 N2 C1 C3 1.2(2) . . . . ?
N2 C1 C2 F1 -3.6(4) . . . . ?
C3 C1 C2 F1 179.0(3) . . . . ?
N2 C1 C2 F2 -126.4(3) . . . . ?
C3 C1 C2 F2 56.2(3) . . . . ?
N2 C1 C2 F3 120.0(3) . . . . ?
C3 C1 C2 F3 -57.4(4) . . . . ?
N2 C1 C3 C4 4.2(2) . . . . ?
C2 C1 C3 C4 -178.3(2) . . . . ?
N2 N1 C4 C5 129.90(16) . . . . ?
C11 N1 C4 C5 -76.0(2) . . . . ?
N2 N1 C4 C3 8.70(19) . . . . ?
C11 N1 C4 C3 162.84(16) . . . . ?
C1 C3 C4 N1 -7.08(18) . . . . ?
C1 C3 C4 C5 -128.84(17) . . . . ?
N1 C4 C5 C10 -44.1(2) . . . . ?
C3 C4 C5 C10 70.4(2) . . . . ?
N1 C4 C5 C6 138.00(17) . . . . ?
C3 C4 C5 C6 -107.5(2) . . . . ?
C10 C5 C6 C7 -0.6(3) . . . . ?
C4 C5 C6 C7 177.36(19) . . . . ?
C5 C6 C7 C8 0.5(4) . . . . ?
C6 C7 C8 C9 0.1(4) . . . . ?
C7 C8 C9 C10 -0.5(4) . . . . ?
C6 C5 C10 C9 0.2(3) . . . . ?
C4 C5 C10 C9 -177.7(2) . . . . ?
C8 C9 C10 C5 0.3(4) . . . . ?
N2 N1 C11 C12 172.76(17) . . . . ?
C4 N1 C11 C12 19.9(3) . . . . ?
N2 N1 C11 C16 -9.8(2) . . . . ?
C4 N1 C11 C16 -162.62(16) . . . . ?
C16 C11 C12 C13 -0.6(3) . . . . ?
N1 C11 C12 C13 176.98(18) . . . . ?
C11 C12 C13 C14 -0.2(3) . . . . ?
C17 O1 C14 C13 180.0(2) . . . . ?
C17 O1 C14 C15 0.8(3) . . . . ?
C12 C13 C14 O1 -178.71(19) . . . . ?
C12 C13 C14 C15 0.5(3) . . . . ?
O1 C14 C15 C16 179.06(19) . . . . ?
C13 C14 C15 C16 -0.1(3) . . . . ?
C14 C15 C16 C11 -0.7(3) . . . . ?
C12 C11 C16 C15 1.0(3) . . . . ?
N1 C11 C16 C15 -176.55(17) . . . . ?

_refine_diff_density_max         0.368
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.044

####################################################################### 
# 
# 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_6b
_database_code_depnum_ccdc_archive 'CCDC 2349835'
loop_
_audit_author_name
_audit_author_address
'Tarun Kanti Panda'
;IIT Hyderabad
India
;
_audit_update_record             
;
2024-04-21 deposited with the CCDC.	2024-11-01 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         'C18 H14 F3 N3'
_chemical_formula_sum            'C18 H14 F3 N3'
_chemical_formula_weight         329.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
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'
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'

_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                   7.0003(5)
_cell_length_b                   10.2027(7)
_cell_length_c                   12.3065(8)
_cell_angle_alpha                105.651(2)
_cell_angle_beta                 105.770(2)
_cell_angle_gamma                101.840(2)
_cell_volume                     776.85(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    23404
_cell_measurement_theta_min      2.173
_cell_measurement_theta_max      27.188

_exptl_crystal_description       plates
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_F_000             340
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.110
_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  0.987
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Bruker APEX-II CCD'
_diffrn_measurement_device_type  'φ and ω scans'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23404
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.173
_diffrn_reflns_theta_max         27.188
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3427
_reflns_number_gt                3087
_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       'SAINT V8.38A (Bruker, 2018)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'ORTEP III and WINGX'
_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)+(0.0464P)²+0.2291P] 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         3427
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.0990
_refine_ls_wR_factor_gt          0.0959
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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
N1 N 0.52774(15) 0.67046(10) 0.21203(9) 0.0282(2) Uani 1 1 d . . . . .
N2 N 0.2029(2) -0.04460(12) -0.06899(12) 0.0459(3) Uani 1 1 d . . . . .
N3 N 0.38800(15) 0.74657(10) 0.20897(8) 0.0260(2) Uani 1 1 d . . . . .
F1 F 0.17254(12) 0.93283(8) 0.21547(8) 0.0469(2) Uani 1 1 d . . . . .
F2 F 0.39503(13) 1.04381(8) 0.39384(7) 0.0430(2) Uani 1 1 d . . . . .
F3 F 0.45123(13) 1.09524(8) 0.24532(7) 0.0423(2) Uani 1 1 d . . . . .
C1 C 0.7797(3) 0.65442(19) 0.65443(14) 0.0550(4) Uani 1 1 d . . . . .
H1A H 0.808600 0.572328 0.674787 0.083 Uiso 1 1 calc R U . . .
H1B H 0.628890 0.635567 0.619935 0.083 Uiso 1 1 calc R U . . .
H1C H 0.837346 0.739501 0.727324 0.083 Uiso 1 1 calc R U . . .
C2 C 0.8781(2) 0.67874(13) 0.56431(11) 0.0342(3) Uani 1 1 d . . . . .
C3 C 0.76996(19) 0.70349(12) 0.46259(11) 0.0294(2) Uani 1 1 d . . . . .
H3 H 0.630653 0.705477 0.449744 0.035 Uiso 1 1 calc R U . . .
C4 C 0.86185(17) 0.72537(11) 0.37943(10) 0.0246(2) Uani 1 1 d . . . . .
C5 C 0.74733(17) 0.76124(12) 0.27332(10) 0.0263(2) Uani 1 1 d . . . . .
H5 H 0.822122 0.752400 0.214328 0.032 Uiso 1 1 calc R U . . .
C6 C 0.45945(18) 0.52489(11) 0.15044(9) 0.0250(2) Uani 1 1 d . . . . .
C7 C 0.60415(19) 0.44864(13) 0.14428(10) 0.0299(2) Uani 1 1 d . . . . .
H7 H 0.749009 0.497619 0.179996 0.036 Uiso 1 1 calc R U . . .
C8 C 0.5363(2) 0.30246(13) 0.08635(11) 0.0318(3) Uani 1 1 d . . . . .
H8 H 0.634812 0.251285 0.082461 0.038 Uiso 1 1 calc R U . . .
C9 C 0.3242(2) 0.22978(12) 0.03364(10) 0.0302(3) Uani 1 1 d . . . . .
C10 C 0.2553(2) 0.07682(13) -0.02328(11) 0.0355(3) Uani 1 1 d . . . . .
C11 C 0.48994(18) 0.87908(12) 0.26229(10) 0.0260(2) Uani 1 1 d . . . . .
C12 C 0.72144(18) 0.91285(12) 0.31041(11) 0.0302(3) Uani 1 1 d . . . . .
H12A H 0.778115 0.960810 0.398870 0.036 Uiso 1 1 calc R U . . .
H12B H 0.789475 0.973356 0.272560 0.036 Uiso 1 1 calc R U . . .
C13 C 1.0815(2) 0.67591(13) 0.58071(12) 0.0386(3) Uani 1 1 d . . . . .
H13 H 1.158383 0.659871 0.649843 0.046 Uiso 1 1 calc R U . . .
C14 C 1.17294(19) 0.69593(14) 0.49859(13) 0.0388(3) Uani 1 1 d . . . . .
H14 H 1.311871 0.693141 0.511205 0.047 Uiso 1 1 calc R U . . .
C15 C 1.06392(18) 0.72028(12) 0.39707(12) 0.0318(3) Uani 1 1 d . . . . .
H15 H 1.127537 0.733337 0.340137 0.038 Uiso 1 1 calc R U . . .
C16 C 0.37590(19) 0.98679(12) 0.27804(11) 0.0309(3) Uani 1 1 d . . . . .
C17 C 0.24619(18) 0.45160(12) 0.09516(10) 0.0278(2) Uani 1 1 d . . . . .
H17 H 0.147304 0.502735 0.097189 0.033 Uiso 1 1 calc R U . . .
C18 C 0.17931(19) 0.30562(12) 0.03785(10) 0.0306(3) Uani 1 1 d . . . . .
H18 H 0.034587 0.256435 0.001167 0.037 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
N1 N3 1.3670(13) . ?
N1 C6 1.3832(14) . ?
N1 C5 1.4827(14) . ?
N2 C10 1.1449(17) . ?
N3 C11 1.2801(14) . ?
F1 C16 1.3328(14) . ?
F2 C16 1.3432(15) . ?
F3 C16 1.3345(14) . ?
C1 C2 1.5035(19) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C13 1.390(2) . ?
C2 C3 1.3921(17) . ?
C3 C4 1.3903(16) . ?
C3 H3 0.9500 . ?
C4 C15 1.3857(16) . ?
C4 C5 1.5136(15) . ?
C5 C12 1.5533(16) . ?
C5 H5 1.0000 . ?
C6 C17 1.4021(16) . ?
C6 C7 1.4037(16) . ?
C7 C8 1.3819(16) . ?
C7 H7 0.9500 . ?
C8 C9 1.3928(18) . ?
C8 H8 0.9500 . ?
C9 C18 1.3999(18) . ?
C9 C10 1.4410(16) . ?
C11 C16 1.4872(16) . ?
C11 C12 1.4949(16) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.372(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.3899(19) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C17 C18 1.3794(16) . ?
C17 H17 0.9500 . ?
C18 H18 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
N3 N1 C6 119.87(9) . . ?
N3 N1 C5 113.38(9) . . ?
C6 N1 C5 126.39(9) . . ?
C11 N3 N1 108.07(9) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C13 C2 C3 118.18(12) . . ?
C13 C2 C1 120.19(12) . . ?
C3 C2 C1 121.63(13) . . ?
C4 C3 C2 121.28(11) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C15 C4 C3 119.42(11) . . ?
C15 C4 C5 119.78(10) . . ?
C3 C4 C5 120.74(10) . . ?
N1 C5 C4 113.08(9) . . ?
N1 C5 C12 101.58(9) . . ?
C4 C5 C12 112.99(9) . . ?
N1 C5 H5 109.6 . . ?
C4 C5 H5 109.6 . . ?
C12 C5 H5 109.6 . . ?
N1 C6 C17 120.70(10) . . ?
N1 C6 C7 119.99(10) . . ?
C17 C6 C7 119.31(10) . . ?
C8 C7 C6 120.13(11) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C9 120.33(11) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C8 C9 C18 119.77(11) . . ?
C8 C9 C10 119.82(11) . . ?
C18 C9 C10 120.41(12) . . ?
N2 C10 C9 179.06(15) . . ?
N3 C11 C16 119.70(10) . . ?
N3 C11 C12 115.70(10) . . ?
C16 C11 C12 124.52(10) . . ?
C11 C12 C5 101.26(9) . . ?
C11 C12 H12A 111.5 . . ?
C5 C12 H12A 111.5 . . ?
C11 C12 H12B 111.5 . . ?
C5 C12 H12B 111.5 . . ?
H12A C12 H12B 109.3 . . ?
C14 C13 C2 121.00(12) . . ?
C14 C13 H13 119.5 . . ?
C2 C13 H13 119.5 . . ?
C13 C14 C15 120.53(12) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C4 C15 C14 119.57(12) . . ?
C4 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
F1 C16 F3 107.76(10) . . ?
F1 C16 F2 106.60(10) . . ?
F3 C16 F2 106.35(9) . . ?
F1 C16 C11 113.11(10) . . ?
F3 C16 C11 111.45(10) . . ?
F2 C16 C11 111.22(10) . . ?
C18 C17 C6 120.31(11) . . ?
C18 C17 H17 119.8 . . ?
C6 C17 H17 119.8 . . ?
C17 C18 C9 120.14(11) . . ?
C17 C18 H18 119.9 . . ?
C9 C18 H18 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
C6 N1 N3 C11 -173.87(10) . . . . ?
C5 N1 N3 C11 -0.34(13) . . . . ?
C13 C2 C3 C4 -0.21(18) . . . . ?
C1 C2 C3 C4 -179.76(12) . . . . ?
C2 C3 C4 C15 1.01(17) . . . . ?
C2 C3 C4 C5 -176.18(10) . . . . ?
N3 N1 C5 C4 121.72(10) . . . . ?
C6 N1 C5 C4 -65.25(14) . . . . ?
N3 N1 C5 C12 0.34(12) . . . . ?
C6 N1 C5 C12 173.37(10) . . . . ?
C15 C4 C5 N1 137.70(11) . . . . ?
C3 C4 C5 N1 -45.13(14) . . . . ?
C15 C4 C5 C12 -107.60(12) . . . . ?
C3 C4 C5 C12 69.58(13) . . . . ?
N3 N1 C6 C17 -6.72(16) . . . . ?
C5 N1 C6 C17 -179.34(10) . . . . ?
N3 N1 C6 C7 174.19(10) . . . . ?
C5 N1 C6 C7 1.57(17) . . . . ?
N1 C6 C7 C8 177.79(10) . . . . ?
C17 C6 C7 C8 -1.31(17) . . . . ?
C6 C7 C8 C9 0.05(18) . . . . ?
C7 C8 C9 C18 0.97(17) . . . . ?
C7 C8 C9 C10 -178.09(11) . . . . ?
N1 N3 C11 C16 -176.81(10) . . . . ?
N1 N3 C11 C12 0.19(13) . . . . ?
N3 C11 C12 C5 0.02(13) . . . . ?
C16 C11 C12 C5 176.86(10) . . . . ?
N1 C5 C12 C11 -0.20(11) . . . . ?
C4 C5 C12 C11 -121.64(10) . . . . ?
C3 C2 C13 C14 -0.45(19) . . . . ?
C1 C2 C13 C14 179.10(13) . . . . ?
C2 C13 C14 C15 0.3(2) . . . . ?
C3 C4 C15 C14 -1.14(17) . . . . ?
C5 C4 C15 C14 176.07(10) . . . . ?
C13 C14 C15 C4 0.49(19) . . . . ?
N3 C11 C16 F1 -10.48(16) . . . . ?
C12 C11 C16 F1 172.80(10) . . . . ?
N3 C11 C16 F3 -132.07(11) . . . . ?
C12 C11 C16 F3 51.21(15) . . . . ?
N3 C11 C16 F2 109.45(12) . . . . ?
C12 C11 C16 F2 -67.27(14) . . . . ?
N1 C6 C17 C18 -177.53(10) . . . . ?
C7 C6 C17 C18 1.56(16) . . . . ?
C6 C17 C18 C9 -0.55(17) . . . . ?
C8 C9 C18 C17 -0.72(17) . . . . ?
C10 C9 C18 C17 178.33(11) . . . . ?

_refine_diff_density_max         0.258
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.039

####################################################################### 
# 
# 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_6d
_database_code_depnum_ccdc_archive 'CCDC 2349836'
loop_
_audit_author_name
_audit_author_address
'Tarun Kanti Panda'
;IIT Hyderabad
India
;
_audit_update_record             
;
2024-04-21 deposited with the CCDC.	2024-11-01 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         'C16 H12 Cl F3 N2'
_chemical_formula_sum            'C16 H12 Cl F3 N2'
_chemical_formula_weight         324.73

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cl Cl 0.1484 0.1585 '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'
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'

_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                   13.9662(18)
_cell_length_b                   6.6425(8)
_cell_length_c                   16.868(2)
_cell_angle_alpha                90
_cell_angle_beta                 106.588(5)
_cell_angle_gamma                90
_cell_volume                     1499.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    305(2)
_cell_measurement_reflns_used    19966
_cell_measurement_theta_min      2.235
_cell_measurement_theta_max      27.125

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    0.284
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.947
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      305(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19966
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_av_R_equivalents  0.0577
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.235
_diffrn_reflns_theta_max         27.125
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3314
_reflns_number_gt                2330
_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       'SAINT V8.38A (Bruker, 2018)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_publication_material  'ORTEP III and WinGX'
_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)+(0.0611P)²+0.4689P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3314
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0728
_refine_ls_R_factor_gt           0.0495
_refine_ls_wR_factor_ref         0.1441
_refine_ls_wR_factor_gt          0.1281
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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
Cl1 Cl 0.59310(5) 0.79099(13) 0.63058(4) 0.0881(3) Uani 1 1 d . . . . .
F1 F 0.18513(13) 0.2675(3) 0.24998(11) 0.1001(6) Uani 1 1 d . . . . .
F2 F 0.1265(2) 0.0297(2) 0.30474(12) 0.1408(10) Uani 1 1 d . . . . .
F3 F 0.03129(13) 0.2482(3) 0.23365(11) 0.1166(7) Uani 1 1 d . . . . .
N1 N 0.12628(14) 0.4166(3) 0.48665(11) 0.0584(4) Uani 1 1 d . . . . .
N2 N 0.11805(13) 0.2681(2) 0.42919(11) 0.0542(4) Uani 1 1 d . . . . .
C1 C 0.46852(16) 0.7384(3) 0.58111(13) 0.0569(5) Uani 1 1 d . . . . .
C2 C 0.40256(18) 0.8925(3) 0.55236(15) 0.0669(6) Uani 1 1 d . . . . .
H2 H 0.424303 1.025472 0.558425 0.080 Uiso 1 1 calc R U . . .
C3 C 0.30348(17) 0.8484(3) 0.51428(14) 0.0613(5) Uani 1 1 d . . . . .
H3 H 0.258583 0.952699 0.494591 0.074 Uiso 1 1 calc R U . . .
C4 C 0.27003(14) 0.6522(3) 0.50499(11) 0.0468(4) Uani 1 1 d . . . . .
C5 C 0.16165(16) 0.6081(3) 0.46006(13) 0.0539(5) Uani 1 1 d . . . . .
C6 C 0.12475(14) 0.3679(3) 0.56661(13) 0.0544(5) Uani 1 1 d . . . . .
C7 C 0.14277(17) 0.5149(4) 0.62745(15) 0.0704(6) Uani 1 1 d . . . . .
H7 H 0.155241 0.646739 0.614736 0.084 Uiso 1 1 calc R U . . .
C8 C 0.1422(2) 0.4659(5) 0.70685(17) 0.0864(8) Uani 1 1 d . . . . .
H8 H 0.154837 0.565032 0.747449 0.104 Uiso 1 1 calc R U . . .
C9 C 0.1233(2) 0.2722(6) 0.7265(2) 0.0965(10) Uani 1 1 d . . . . .
H9 H 0.123416 0.239788 0.780138 0.116 Uiso 1 1 calc R U . . .
C10 C 0.14436(18) 0.5688(3) 0.36698(13) 0.0628(6) Uani 1 1 d . . . . .
H10A H 0.085965 0.639862 0.333749 0.075 Uiso 1 1 calc R U . . .
H10B H 0.202118 0.606688 0.349265 0.075 Uiso 1 1 calc R U . . .
C11 C 0.12872(15) 0.3468(3) 0.36312(13) 0.0534(5) Uani 1 1 d . . . . .
C12 C 0.11870(19) 0.2212(4) 0.28922(14) 0.0661(6) Uani 1 1 d . . . . .
C13 C 0.1041(2) 0.1263(5) 0.6659(2) 0.0901(9) Uani 1 1 d . . . . .
H13 H 0.090646 -0.004836 0.678861 0.108 Uiso 1 1 calc R U . . .
C14 C 0.10451(17) 0.1725(4) 0.58647(15) 0.0663(6) Uani 1 1 d . . . . .
H14 H 0.091263 0.072859 0.546058 0.080 Uiso 1 1 calc R U . . .
C15 C 0.33822(16) 0.5004(3) 0.53438(13) 0.0556(5) Uani 1 1 d . . . . .
H15 H 0.316847 0.367214 0.528641 0.067 Uiso 1 1 calc R U . . .
C16 C 0.43728(16) 0.5421(3) 0.57205(13) 0.0595(5) Uani 1 1 d . . . . .
H16 H 0.482566 0.438113 0.591153 0.071 Uiso 1 1 calc R U . . .
H5 H 0.1191(16) 0.721(3) 0.4695(13) 0.058(6) Uiso 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 C1 1.737(2) . ?
F1 C12 1.321(3) . ?
F2 C12 1.297(3) . ?
F3 C12 1.322(3) . ?
N1 N2 1.365(2) . ?
N1 C6 1.393(3) . ?
N1 C5 1.480(3) . ?
N2 C11 1.278(3) . ?
C1 C16 1.369(3) . ?
C1 C2 1.370(3) . ?
C2 C3 1.381(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(3) . ?
C3 H3 0.9300 . ?
C4 C15 1.378(3) . ?
C4 C5 1.516(3) . ?
C5 C10 1.541(3) . ?
C5 H5 1.00(2) . ?
C6 C7 1.386(3) . ?
C6 C14 1.390(3) . ?
C7 C8 1.381(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.373(5) . ?
C8 H8 0.9300 . ?
C9 C13 1.378(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.489(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.473(3) . ?
C13 C14 1.377(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.376(3) . ?
C15 H15 0.9300 . ?
C16 H16 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
N2 N1 C6 119.89(17) . . ?
N2 N1 C5 111.94(16) . . ?
C6 N1 C5 126.29(17) . . ?
C11 N2 N1 108.46(16) . . ?
C16 C1 C2 120.8(2) . . ?
C16 C1 Cl1 119.26(17) . . ?
C2 C1 Cl1 119.98(18) . . ?
C1 C2 C3 119.3(2) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C4 C3 C2 121.1(2) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C15 118.29(19) . . ?
C3 C4 C5 119.85(18) . . ?
C15 C4 C5 121.81(17) . . ?
N1 C5 C4 112.77(16) . . ?
N1 C5 C10 101.23(16) . . ?
C4 C5 C10 112.70(18) . . ?
N1 C5 H5 109.4(12) . . ?
C4 C5 H5 109.3(12) . . ?
C10 C5 H5 111.3(13) . . ?
C7 C6 C14 119.1(2) . . ?
C7 C6 N1 120.2(2) . . ?
C14 C6 N1 120.7(2) . . ?
C8 C7 C6 120.1(3) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C9 C8 C7 120.6(3) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C13 119.4(3) . . ?
C8 C9 H9 120.3 . . ?
C13 C9 H9 120.3 . . ?
C11 C10 C5 100.97(17) . . ?
C11 C10 H10A 111.6 . . ?
C5 C10 H10A 111.6 . . ?
C11 C10 H10B 111.6 . . ?
C5 C10 H10B 111.6 . . ?
H10A C10 H10B 109.4 . . ?
N2 C11 C12 119.99(19) . . ?
N2 C11 C10 114.79(19) . . ?
C12 C11 C10 125.10(19) . . ?
F2 C12 F1 107.4(2) . . ?
F2 C12 F3 106.5(2) . . ?
F1 C12 F3 104.6(2) . . ?
F2 C12 C11 113.7(2) . . ?
F1 C12 C11 112.4(2) . . ?
F3 C12 C11 111.6(2) . . ?
C14 C13 C9 120.7(3) . . ?
C14 C13 H13 119.6 . . ?
C9 C13 H13 119.6 . . ?
C13 C14 C6 120.0(3) . . ?
C13 C14 H14 120.0 . . ?
C6 C14 H14 120.0 . . ?
C16 C15 C4 121.28(19) . . ?
C16 C15 H15 119.4 . . ?
C4 C15 H15 119.4 . . ?
C1 C16 C15 119.3(2) . . ?
C1 C16 H16 120.3 . . ?
C15 C16 H16 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
C6 N1 N2 C11 -175.29(18) . . . . ?
C5 N1 N2 C11 -9.9(2) . . . . ?
C16 C1 C2 C3 0.4(3) . . . . ?
Cl1 C1 C2 C3 -179.03(18) . . . . ?
C1 C2 C3 C4 0.2(4) . . . . ?
C2 C3 C4 C15 -0.3(3) . . . . ?
C2 C3 C4 C5 -177.7(2) . . . . ?
N2 N1 C5 C4 -104.91(19) . . . . ?
C6 N1 C5 C4 59.3(3) . . . . ?
N2 N1 C5 C10 15.8(2) . . . . ?
C6 N1 C5 C10 179.99(19) . . . . ?
C3 C4 C5 N1 -153.76(18) . . . . ?
C15 C4 C5 N1 28.9(3) . . . . ?
C3 C4 C5 C10 92.4(2) . . . . ?
C15 C4 C5 C10 -84.9(2) . . . . ?
N2 N1 C6 C7 173.71(19) . . . . ?
C5 N1 C6 C7 10.6(3) . . . . ?
N2 N1 C6 C14 -6.8(3) . . . . ?
C5 N1 C6 C14 -169.9(2) . . . . ?
C14 C6 C7 C8 1.1(3) . . . . ?
N1 C6 C7 C8 -179.3(2) . . . . ?
C6 C7 C8 C9 -0.4(4) . . . . ?
C7 C8 C9 C13 -0.4(4) . . . . ?
N1 C5 C10 C11 -14.5(2) . . . . ?
C4 C5 C10 C11 106.23(19) . . . . ?
N1 N2 C11 C12 -177.25(19) . . . . ?
N1 N2 C11 C10 -1.1(2) . . . . ?
C5 C10 C11 N2 10.7(2) . . . . ?
C5 C10 C11 C12 -173.4(2) . . . . ?
N2 C11 C12 F2 -17.9(3) . . . . ?
C10 C11 C12 F2 166.4(2) . . . . ?
N2 C11 C12 F1 -140.2(2) . . . . ?
C10 C11 C12 F1 44.1(3) . . . . ?
N2 C11 C12 F3 102.6(3) . . . . ?
C10 C11 C12 F3 -73.1(3) . . . . ?
C8 C9 C13 C14 0.5(5) . . . . ?
C9 C13 C14 C6 0.2(4) . . . . ?
C7 C6 C14 C13 -1.0(3) . . . . ?
N1 C6 C14 C13 179.5(2) . . . . ?
C3 C4 C15 C16 -0.1(3) . . . . ?
C5 C4 C15 C16 177.28(19) . . . . ?
C2 C1 C16 C15 -0.7(3) . . . . ?
Cl1 C1 C16 C15 178.68(16) . . . . ?
C4 C15 C16 C1 0.6(3) . . . . ?

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
C16 H16 F3 0.93 2.62 3.291(3) 130.0 4_666 yes
C16 H16 F3 0.93 2.62 3.291(3) 130.0 4_666 yes

_refine_diff_density_max         0.262
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.044

