# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1055453'
_audit_update_record             
;
2015-03-23 deposited with the CCDC.
2018-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H17 F3 N2 O'
_chemical_formula_sum            'C20 H17 F3 N2 O'
_chemical_formula_weight         358.36

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.2030(7)
_cell_length_b                   10.0784(8)
_cell_length_c                   13.335(2)
_cell_angle_alpha                108.279(9)
_cell_angle_beta                 92.593(10)
_cell_angle_gamma                107.656(8)
_cell_volume                     865.30(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      3.12
_cell_measurement_theta_max      25.00

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             372
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9767
_exptl_absorpt_correction_T_max  0.9808
_exptl_absorpt_process_details   crysalispro

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5952
_diffrn_reflns_av_R_equivalents  0.0143
_diffrn_reflns_av_sigmaI/netI    0.0297
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.10
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3048
_reflns_number_gt                2270
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1318P)²+0.7281P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.034(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3048
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1057
_refine_ls_R_factor_gt           0.0852
_refine_ls_wR_factor_ref         0.2691
_refine_ls_wR_factor_gt          0.2504
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.034
_refine_ls_shift/su_mean         0.003

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.1394(10) 0.2091(5) 0.0596(4) 0.0964(16) Uani 1 1 d . . .
C2 C -0.0522(6) 0.3463(4) 0.1535(3) 0.0593(9) Uani 1 1 d . . .
C3 C 0.0650(6) 0.4738(4) 0.1399(3) 0.0606(9) Uani 1 1 d . . .
H3 H 0.0948 0.4719 0.0724 0.073 Uiso 1 1 calc R . .
C4 C 0.1382(5) 0.6043(4) 0.2260(3) 0.0569(9) Uani 1 1 d . . .
H4 H 0.2162 0.6902 0.2161 0.068 Uiso 1 1 calc R . .
C5 C 0.0960(5) 0.6083(4) 0.3276(3) 0.0468(8) Uani 1 1 d . . .
C6 C -0.0154(5) 0.4773(4) 0.3404(3) 0.0539(9) Uani 1 1 d . . .
H6 H -0.0389 0.4771 0.4084 0.065 Uiso 1 1 calc R . .
C7 C -0.0918(6) 0.3475(4) 0.2541(3) 0.0584(9) Uani 1 1 d . . .
H7 H -0.1696 0.2612 0.2635 0.070 Uiso 1 1 calc R . .
C8 C 0.1648(5) 0.7491(4) 0.4234(3) 0.0479(8) Uani 1 1 d . . .
C9 C 0.1912(5) 0.8825(4) 0.4067(3) 0.0518(8) Uani 1 1 d . . .
H9 H 0.1656 0.8803 0.3371 0.062 Uiso 1 1 calc R . .
C10 C 0.2550(4) 1.0212(4) 0.4905(3) 0.0464(8) Uani 1 1 d . . .
C11 C 0.2330(6) 1.1574(4) 0.3708(3) 0.0629(10) Uani 1 1 d . . .
H11 H 0.0932 1.1412 0.3506 0.076 Uiso 1 1 calc R . .
C12 C 0.3352(8) 1.1059(5) 0.2814(4) 0.0839(13) Uani 1 1 d . . .
H12A H 0.2585 1.0575 0.2104 0.101 Uiso 1 1 calc R . .
H12B H 0.4389 1.0679 0.2946 0.101 Uiso 1 1 calc R . .
C13 C 0.3717(7) 1.2665(5) 0.3336(4) 0.0805(13) Uani 1 1 d . . .
H13A H 0.4977 1.3265 0.3787 0.097 Uiso 1 1 calc R . .
H13B H 0.3172 1.3161 0.2945 0.097 Uiso 1 1 calc R . .
C14 C 0.3517(6) 1.2946(4) 0.5616(3) 0.0606(9) Uani 1 1 d . . .
H14A H 0.2699 1.3520 0.5525 0.073 Uiso 1 1 calc R . .
H14B H 0.4859 1.3482 0.5568 0.073 Uiso 1 1 calc R . .
C15 C 0.3462(5) 1.2824(4) 0.6706(3) 0.0534(9) Uani 1 1 d . . .
C16 C 0.3712(5) 1.4049(4) 0.7608(3) 0.0634(10) Uani 1 1 d . . .
H16 H 0.3896 1.4968 0.7538 0.076 Uiso 1 1 calc R . .
C17 C 0.3694(7) 1.3927(5) 0.8601(3) 0.0774(12) Uani 1 1 d . . .
H17 H 0.3840 1.4755 0.9199 0.093 Uiso 1 1 calc R . .
C18 C 0.3457(7) 1.2575(5) 0.8714(3) 0.0778(12) Uani 1 1 d . . .
H18 H 0.3483 1.2499 0.9391 0.093 Uiso 1 1 calc R . .
C19 C 0.3178(6) 1.1324(5) 0.7819(3) 0.0655(10) Uani 1 1 d . . .
H19 H 0.2990 1.0406 0.7892 0.079 Uiso 1 1 calc R . .
C20 C 0.3185(5) 1.1465(4) 0.6818(3) 0.0528(8) Uani 1 1 d . . .
F1 F -0.1339(11) 0.2183(4) -0.0282(3) 0.237(4) Uani 1 1 d . . .
F2 F -0.3073(10) 0.1330(7) 0.0615(4) 0.265(4) Uani 1 1 d . . .
F3 F -0.0633(16) 0.1137(7) 0.0574(5) 0.292(5) Uani 1 1 d . . .
N1 N 0.2840(4) 1.1515(3) 0.4748(2) 0.0523(7) Uani 1 1 d . . .
N2 N 0.2875(4) 1.0220(3) 0.5905(2) 0.0530(7) Uani 1 1 d . . .
H2 H 0.2488 0.9238 0.6059 0.064 Uiso 1 1 d R . .
O1 O 0.1890(4) 0.7352(3) 0.51399(18) 0.0623(7) Uani 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 F1 1.204(6) . ?
C1 F2 1.226(7) . ?
C1 F3 1.237(7) . ?
C1 C2 1.480(6) . ?
C2 C3 1.378(5) . ?
C2 C7 1.380(5) . ?
C3 C4 1.380(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.392(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.388(5) . ?
C5 C8 1.508(5) . ?
C6 C7 1.379(5) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 O1 1.269(4) . ?
C8 C9 1.389(5) . ?
C9 C10 1.414(5) . ?
C9 H9 0.9300 . ?
C10 N2 1.342(4) . ?
C10 N1 1.349(4) . ?
C11 N1 1.443(4) . ?
C11 C12 1.467(6) . ?
C11 C13 1.474(5) . ?
C11 H11 0.9800 . ?
C12 C13 1.480(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 N1 1.461(4) . ?
C14 C15 1.498(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C20 1.380(5) . ?
C15 C16 1.384(5) . ?
C16 C17 1.368(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.378(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.391(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.386(5) . ?
C19 H19 0.9300 . ?
C20 N2 1.398(4) . ?
N2 H2 1.0315 . ?

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
F1 C1 F2 107.8(7) . . ?
F1 C1 F3 104.0(6) . . ?
F2 C1 F3 95.8(7) . . ?
F1 C1 C2 118.3(4) . . ?
F2 C1 C2 115.4(5) . . ?
F3 C1 C2 112.8(6) . . ?
C3 C2 C7 120.1(3) . . ?
C3 C2 C1 119.8(4) . . ?
C7 C2 C1 120.1(4) . . ?
C2 C3 C4 120.2(3) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 120.4(3) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 118.5(3) . . ?
C6 C5 C8 118.9(3) . . ?
C4 C5 C8 122.6(3) . . ?
C7 C6 C5 121.1(3) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C2 119.6(3) . . ?
C6 C7 H7 120.2 . . ?
C2 C7 H7 120.2 . . ?
O1 C8 C9 125.2(3) . . ?
O1 C8 C5 116.7(3) . . ?
C9 C8 C5 118.1(3) . . ?
C8 C9 C10 123.0(3) . . ?
C8 C9 H9 118.5 . . ?
C10 C9 H9 118.5 . . ?
N2 C10 N1 118.9(3) . . ?
N2 C10 C9 117.7(3) . . ?
N1 C10 C9 123.5(3) . . ?
N1 C11 C12 121.4(3) . . ?
N1 C11 C13 119.0(3) . . ?
C12 C11 C13 60.4(3) . . ?
N1 C11 H11 115.0 . . ?
C12 C11 H11 115.0 . . ?
C13 C11 H11 115.0 . . ?
C11 C12 C13 60.0(3) . . ?
C11 C12 H12A 117.8 . . ?
C13 C12 H12A 117.8 . . ?
C11 C12 H12B 117.8 . . ?
C13 C12 H12B 117.8 . . ?
H12A C12 H12B 114.9 . . ?
C11 C13 C12 59.6(3) . . ?
C11 C13 H13A 117.8 . . ?
C12 C13 H13A 117.8 . . ?
C11 C13 H13B 117.8 . . ?
C12 C13 H13B 117.8 . . ?
H13A C13 H13B 115.0 . . ?
N1 C14 C15 113.7(3) . . ?
N1 C14 H14A 108.8 . . ?
C15 C14 H14A 108.8 . . ?
N1 C14 H14B 108.8 . . ?
C15 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
C20 C15 C16 119.1(3) . . ?
C20 C15 C14 119.3(3) . . ?
C16 C15 C14 121.6(3) . . ?
C17 C16 C15 120.9(4) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C16 C17 C18 119.9(4) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C18 C19 120.3(4) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C20 C19 C18 119.1(4) . . ?
C20 C19 H19 120.5 . . ?
C18 C19 H19 120.5 . . ?
C15 C20 C19 120.7(3) . . ?
C15 C20 N2 119.1(3) . . ?
C19 C20 N2 120.1(3) . . ?
C10 N1 C11 121.6(3) . . ?
C10 N1 C14 123.2(3) . . ?
C11 N1 C14 115.0(3) . . ?
C10 N2 C20 123.8(3) . . ?
C10 N2 H2 120.4 . . ?
C20 N2 H2 113.3 . . ?

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
F1 C1 C2 C3 -12.6(9) . . . . ?
F2 C1 C2 C3 -142.3(7) . . . . ?
F3 C1 C2 C3 109.0(8) . . . . ?
F1 C1 C2 C7 166.0(6) . . . . ?
F2 C1 C2 C7 36.2(9) . . . . ?
F3 C1 C2 C7 -72.5(9) . . . . ?
C7 C2 C3 C4 -2.0(6) . . . . ?
C1 C2 C3 C4 176.5(4) . . . . ?
C2 C3 C4 C5 0.6(6) . . . . ?
C3 C4 C5 C6 2.1(5) . . . . ?
C3 C4 C5 C8 -177.3(3) . . . . ?
C4 C5 C6 C7 -3.4(5) . . . . ?
C8 C5 C6 C7 176.0(3) . . . . ?
C5 C6 C7 C2 2.0(5) . . . . ?
C3 C2 C7 C6 0.8(6) . . . . ?
C1 C2 C7 C6 -177.7(4) . . . . ?
C6 C5 C8 O1 27.6(4) . . . . ?
C4 C5 C8 O1 -153.0(3) . . . . ?
C6 C5 C8 C9 -150.5(3) . . . . ?
C4 C5 C8 C9 28.9(5) . . . . ?
O1 C8 C9 C10 2.0(5) . . . . ?
C5 C8 C9 C10 180.0(3) . . . . ?
C8 C9 C10 N2 -1.3(5) . . . . ?
C8 C9 C10 N1 178.9(3) . . . . ?
N1 C11 C12 C13 -107.9(4) . . . . ?
N1 C11 C13 C12 111.7(4) . . . . ?
N1 C14 C15 C20 12.6(5) . . . . ?
N1 C14 C15 C16 -168.4(3) . . . . ?
C20 C15 C16 C17 0.2(5) . . . . ?
C14 C15 C16 C17 -178.8(3) . . . . ?
C15 C16 C17 C18 1.1(6) . . . . ?
C16 C17 C18 C19 -1.9(7) . . . . ?
C17 C18 C19 C20 1.4(6) . . . . ?
C16 C15 C20 C19 -0.7(5) . . . . ?
C14 C15 C20 C19 178.3(3) . . . . ?
C16 C15 C20 N2 178.2(3) . . . . ?
C14 C15 C20 N2 -2.8(5) . . . . ?
C18 C19 C20 C15 0.0(6) . . . . ?
C18 C19 C20 N2 -178.9(3) . . . . ?
N2 C10 N1 C11 -173.7(3) . . . . ?
C9 C10 N1 C11 6.1(5) . . . . ?
N2 C10 N1 C14 0.8(5) . . . . ?
C9 C10 N1 C14 -179.4(3) . . . . ?
C12 C11 N1 C10 -65.2(5) . . . . ?
C13 C11 N1 C10 -136.4(4) . . . . ?
C12 C11 N1 C14 119.9(4) . . . . ?
C13 C11 N1 C14 48.8(5) . . . . ?
C15 C14 N1 C10 -12.0(5) . . . . ?
C15 C14 N1 C11 162.8(3) . . . . ?
N1 C10 N2 C20 10.9(5) . . . . ?
C9 C10 N2 C20 -168.9(3) . . . . ?
C15 C20 N2 C10 -9.8(5) . . . . ?
C19 C20 N2 C10 169.1(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.826
_refine_diff_density_min         -0.576
_refine_diff_density_rms         0.056
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM, HEXANE'
