# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_20200923_lh_110_2_0m
_database_code_depnum_ccdc_archive 'CCDC 2088404'
_audit_update_record             
;
2021-06-07 deposited with the CCDC.	2021-11-18 downloaded from the CCDC.
;
_audit_creation_date             2020-09-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H15 F3 N2 O'
_chemical_formula_sum            'C19 H15 F3 N2 O'
_chemical_formula_weight         344.33
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   12.2095(6)
_cell_length_b                   12.2629(6)
_cell_length_c                   12.3037(6)
_cell_angle_alpha                90
_cell_angle_beta                 118.7457(17)
_cell_angle_gamma                90
_cell_volume                     1615.13(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6979
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.477
_cell_measurement_theta_min      3.263
_shelx_estimated_absorpt_T_max   0.975
_shelx_estimated_absorpt_T_min   0.972
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.23
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            23123
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.243
_diffrn_reflns_theta_max         27.512
_diffrn_reflns_theta_min         3.263
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'D8 QUEST'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71076
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2475
_reflns_number_total             3703
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3703
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1130
_refine_ls_R_factor_gt           0.0713
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0410P)²+1.1607P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1331
_refine_ls_wR_factor_ref         0.1474
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4AA(H4AA,H4AB)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C15(H15), C5AA(H5AA),
 C6AA(H6AA), C7AA(H7AA)
2.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.37754(18) 0.06123(16) 0.14253(19) 0.0369(5) Uani 1 1 d . . . . .
N3 N 0.62652(18) 0.03170(17) 0.20004(19) 0.0402(5) Uani 1 1 d . . . . .
C0AA C 0.4186(2) -0.03796(18) 0.1208(2) 0.0337(5) Uani 1 1 d . . . . .
C1AA C 0.4584(2) 0.13736(18) 0.1942(2) 0.0342(5) Uani 1 1 d . . . . .
C2AA C 0.5427(2) -0.05466(19) 0.1489(2) 0.0363(6) Uani 1 1 d . . . . .
C3AA C 0.5923(2) 0.1285(2) 0.2312(2) 0.0387(6) Uani 1 1 d . . . . .
O2 O 0.66561(17) 0.20281(15) 0.28235(19) 0.0560(5) Uani 1 1 d . . . . .
C4 C 0.4905(3) -0.2377(2) 0.0750(3) 0.0563(8) Uani 1 1 d . . . . .
H4 H 0.5145 -0.3053 0.0592 0.068 Uiso 1 1 calc R . . . .
C6 C 0.3473(2) 0.3089(2) 0.1288(3) 0.0437(6) Uani 1 1 d . . . . .
H6 H 0.3310 0.2863 0.0503 0.052 Uiso 1 1 calc R . . . .
C7 C 0.3325(3) -0.1226(2) 0.0703(2) 0.0445(6) Uani 1 1 d . . . . .
H7 H 0.2500 -0.1114 0.0519 0.053 Uiso 1 1 calc R . . . .
C8 C 0.5777(3) -0.1565(2) 0.1250(3) 0.0502(7) Uani 1 1 d . . . . .
H8 H 0.6599 -0.1692 0.1431 0.060 Uiso 1 1 calc R . . . .
C9 C 0.3683(3) -0.2218(2) 0.0475(3) 0.0539(7) Uani 1 1 d . . . . .
H9 H 0.3105 -0.2781 0.0137 0.065 Uiso 1 1 calc R . . . .
C10 C 0.4557(2) 0.2601(2) 0.3559(2) 0.0389(6) Uani 1 1 d . . . . .
C11 C 0.4215(3) 0.1837(2) 0.4165(3) 0.0541(7) Uani 1 1 d . . . . .
H11 H 0.3747 0.1233 0.3733 0.065 Uiso 1 1 calc R . . . .
C14 C 0.2930(3) 0.4149(2) 0.1374(3) 0.0495(7) Uani 1 1 d . . . . .
C15 C 0.5277(3) 0.3477(2) 0.4229(3) 0.0535(7) Uani 1 1 d . . . . .
H15 H 0.5528 0.3994 0.3841 0.064 Uiso 1 1 calc R . . . .
C16 C 0.4171(2) 0.24359(19) 0.2230(2) 0.0371(6) Uani 1 1 d . . . . .
F1 F 0.25552(18) 0.41845(14) 0.22195(17) 0.0699(5) Uani 1 1 d . . . . .
F2 F 0.37411(19) 0.49769(14) 0.1647(2) 0.0790(6) Uani 1 1 d . . . . .
F3 F 0.19547(18) 0.44130(15) 0.02945(16) 0.0734(6) Uani 1 1 d . . . . .
C4AA C 0.7577(2) 0.0213(2) 0.2246(3) 0.0507(7) Uani 1 1 d . . . . .
H4AA H 0.7908 0.0931 0.2242 0.061 Uiso 1 1 calc R . . . .
H4AB H 0.7596 -0.0213 0.1591 0.061 Uiso 1 1 calc R . . . .
C5 C 0.8375(3) -0.0322(3) 0.3463(3) 0.0666(9) Uani 1 1 d . . . . .
H5A H 0.8055 -0.1037 0.3463 0.100 Uiso 1 1 calc GR . . . .
H5B H 0.8370 0.0106 0.4113 0.100 Uiso 1 1 calc GR . . . .
H5C H 0.9215 -0.0381 0.3596 0.100 Uiso 1 1 calc GR . . . .
C5AA C 0.5625(3) 0.3590(3) 0.5464(3) 0.0679(9) Uani 1 1 d . . . . .
H5AA H 0.6110 0.4183 0.5904 0.081 Uiso 1 1 calc R . . . .
C6AA C 0.5267(3) 0.2841(3) 0.6052(3) 0.0688(9) Uani 1 1 d . . . . .
H6AA H 0.5500 0.2928 0.6886 0.083 Uiso 1 1 calc R . . . .
C7AA C 0.4560(3) 0.1957(3) 0.5402(3) 0.0692(9) Uani 1 1 d . . . . .
H7AA H 0.4316 0.1442 0.5798 0.083 Uiso 1 1 calc R . . . .


_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 C0AA 1.390(3) . ?
N1 C1AA 1.284(3) . ?
N3 C2AA 1.395(3) . ?
N3 C3AA 1.373(3) . ?
N3 C4AA 1.486(3) . ?
C0AA C2AA 1.398(3) . ?
C0AA C7 1.393(3) . ?
C1AA C3AA 1.475(3) . ?
C1AA C16 1.500(3) . ?
C2AA C8 1.397(3) . ?
C3AA O2 1.219(3) . ?
C4 C8 1.368(4) . ?
C4 C9 1.377(4) . ?
C6 C14 1.486(3) . ?
C6 C16 1.327(3) . ?
C7 C9 1.367(4) . ?
C10 C11 1.381(4) . ?
C10 C15 1.382(3) . ?
C10 C16 1.481(4) . ?
C11 C7AA 1.379(4) . ?
C14 F1 1.323(3) . ?
C14 F2 1.343(3) . ?
C14 F3 1.329(3) . ?
C15 C5AA 1.374(4) . ?
C4AA C5 1.490(4) . ?
C5AA C6AA 1.363(5) . ?
C6AA C7AA 1.377(5) . ?

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
C1AA N1 C0AA 118.0(2) . . ?
C2AA N3 C4AA 120.8(2) . . ?
C3AA N3 C2AA 121.8(2) . . ?
C3AA N3 C4AA 117.4(2) . . ?
N1 C0AA C2AA 121.9(2) . . ?
N1 C0AA C7 118.2(2) . . ?
C7 C0AA C2AA 119.8(2) . . ?
N1 C1AA C3AA 125.0(2) . . ?
N1 C1AA C16 118.9(2) . . ?
C3AA C1AA C16 116.1(2) . . ?
N3 C2AA C0AA 118.2(2) . . ?
N3 C2AA C8 122.8(2) . . ?
C8 C2AA C0AA 119.0(2) . . ?
N3 C3AA C1AA 114.7(2) . . ?
O2 C3AA N3 123.0(2) . . ?
O2 C3AA C1AA 122.3(2) . . ?
C8 C4 C9 121.6(3) . . ?
C16 C6 C14 125.9(2) . . ?
C9 C7 C0AA 120.5(3) . . ?
C4 C8 C2AA 119.6(3) . . ?
C7 C9 C4 119.4(3) . . ?
C11 C10 C15 118.5(3) . . ?
C11 C10 C16 119.0(2) . . ?
C15 C10 C16 122.5(2) . . ?
C7AA C11 C10 120.8(3) . . ?
F1 C14 C6 114.8(2) . . ?
F1 C14 F2 105.7(2) . . ?
F1 C14 F3 107.2(2) . . ?
F2 C14 C6 112.2(2) . . ?
F3 C14 C6 111.0(2) . . ?
F3 C14 F2 105.3(2) . . ?
C5AA C15 C10 120.5(3) . . ?
C6 C16 C1AA 117.8(2) . . ?
C6 C16 C10 127.7(2) . . ?
C10 C16 C1AA 114.5(2) . . ?
N3 C4AA C5 111.2(2) . . ?
C6AA C5AA C15 120.8(3) . . ?
C5AA C6AA C7AA 119.6(3) . . ?
C6AA C7AA C11 119.9(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
