# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_T
_database_code_depnum_ccdc_archive 'CCDC 1579956'
_audit_update_record             
;
2018-09-30 deposited with the CCDC.
2018-10-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H15 F3 N2 O3'
_chemical_formula_weight         364.32

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

_cell_length_a                   17.298(2)
_cell_length_b                   5.9353(8)
_cell_length_c                   33.483(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3437.7(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7124
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      26.52

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_F_000             1504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.118
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            25163
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_av_R_equivalents  0.1016
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         1.693
_diffrn_reflns_theta_max         25.995
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3381
_reflns_number_gt                2596
_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    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0728P)²+0.8067P] 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         3381
_refine_ls_number_parameters     264
_refine_ls_number_restraints     55
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_gt           0.0529
_refine_ls_wR_factor_ref         0.1451
_refine_ls_wR_factor_gt          0.1351
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.126
_refine_ls_shift/su_max          0.004
_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
C1 C 0.1303(3) 0.4819(8) 0.01592(10) 0.1321(15) Uani 1 1 d D U . . .
F1 F 0.1173(11) 0.646(2) -0.0084(3) 0.203(7) Uani 0.447(18) 1 d D U P A 1
F2 F 0.1941(5) 0.378(3) 0.0055(4) 0.168(6) Uani 0.447(18) 1 d D U P A 1
F3 F 0.0735(6) 0.327(2) 0.0098(4) 0.173(5) Uani 0.447(18) 1 d D U P A 1
F1' F 0.0777(5) 0.583(2) -0.0066(3) 0.162(4) Uani 0.553(18) 1 d D U P A 2
F2' F 0.1970(4) 0.532(3) -0.0019(3) 0.198(5) Uani 0.553(18) 1 d D U P A 2
F3' F 0.1194(11) 0.2659(12) 0.0135(3) 0.214(6) Uani 0.553(18) 1 d D U P A 2
C2 C 0.12929(18) 0.5621(5) 0.05821(7) 0.0844(8) Uani 1 1 d D . . . .
C3 C 0.06465(17) 0.6600(6) 0.07438(8) 0.0871(8) Uani 1 1 d . . . . .
H3 H 0.0209 0.6805 0.0586 0.104 Uiso 1 1 calc R U . . .
C4 C 0.06383(13) 0.7284(4) 0.11367(7) 0.0648(6) Uani 1 1 d . . . . .
H4 H 0.0199 0.7970 0.1241 0.078 Uiso 1 1 calc R U . . .
C5 C 0.12783(10) 0.6956(3) 0.13760(5) 0.0423(4) Uani 1 1 d . . . . .
C6 C 0.19291(12) 0.5966(4) 0.12142(6) 0.0575(5) Uani 1 1 d . . . . .
H6 H 0.2368 0.5760 0.1370 0.069 Uiso 1 1 calc R U . . .
C7 C 0.19272(16) 0.5287(5) 0.08228(7) 0.0769(7) Uani 1 1 d . . . . .
H7 H 0.2363 0.4588 0.0718 0.092 Uiso 1 1 calc R U . . .
N1 N 0.12588(8) 0.7628(2) 0.17788(4) 0.0377(3) Uani 1 1 d . . . . .
C8 C 0.06896(9) 0.9230(3) 0.19384(5) 0.0378(4) Uani 1 1 d . . . . .
H8 H 0.0166 0.8719 0.1873 0.045 Uiso 1 1 calc R U . . .
C9 C 0.08159(9) 0.9110(3) 0.23834(5) 0.0397(4) Uani 1 1 d . . . . .
N2 N 0.14156(8) 0.7664(2) 0.24294(4) 0.0425(4) Uani 1 1 d . . . . .
C10 C 0.17068(9) 0.6745(3) 0.20763(5) 0.0372(4) Uani 1 1 d . . . . .
C11 C 0.08096(11) 1.1612(3) 0.17851(6) 0.0482(5) Uani 1 1 d . . . . .
H11A H 0.1325 1.2099 0.1848 0.072 Uiso 1 1 calc R U . . .
H11B H 0.0443 1.2603 0.1910 0.072 Uiso 1 1 calc R U . . .
H11C H 0.0737 1.1640 0.1501 0.072 Uiso 1 1 calc R U . . .
C12 C 0.14750(12) 0.4897(3) 0.29184(6) 0.0498(5) Uani 1 1 d . . . . .
H12A H 0.1834 0.3764 0.2822 0.060 Uiso 1 1 calc R U . . .
H12B H 0.0968 0.4576 0.2808 0.060 Uiso 1 1 calc R U . . .
C13 C 0.14417(10) 0.4845(3) 0.33627(6) 0.0465(4) Uani 1 1 d . . . . .
C14 C 0.11306(12) 0.6609(4) 0.35774(6) 0.0567(5) Uani 1 1 d . . . . .
H14 H 0.0948 0.7878 0.3445 0.068 Uiso 1 1 calc R U . . .
C15 C 0.10889(17) 0.6500(5) 0.39869(7) 0.0791(7) Uani 1 1 d . . . . .
H15 H 0.0875 0.7693 0.4129 0.095 Uiso 1 1 calc R U . . .
C16 C 0.13586(19) 0.4654(6) 0.41871(8) 0.0924(9) Uani 1 1 d . . . . .
H16 H 0.1335 0.4599 0.4464 0.111 Uiso 1 1 calc R U . . .
C17 C 0.16631(17) 0.2888(6) 0.39771(9) 0.0910(9) Uani 1 1 d . . . . .
H17 H 0.1842 0.1622 0.4112 0.109 Uiso 1 1 calc R U . . .
C18 C 0.17064(13) 0.2973(4) 0.35661(8) 0.0683(6) Uani 1 1 d . . . . .
H18 H 0.1914 0.1766 0.3425 0.082 Uiso 1 1 calc R U . . .
O1 O 0.22294(7) 0.5415(2) 0.20605(4) 0.0495(3) Uani 1 1 d . . . . .
O2 O 0.04733(8) 1.0125(2) 0.26403(4) 0.0545(4) Uani 1 1 d . . . . .
O3 O 0.17289(7) 0.7126(2) 0.27944(4) 0.0480(3) 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 1.289(8) . ?
C1 F3' 1.298(7) . ?
C1 F2 1.313(7) . ?
C1 F1' 1.325(7) . ?
C1 F2' 1.333(8) . ?
C1 F3 1.360(8) . ?
C1 C2 1.494(4) . ?
C2 C3 1.372(4) . ?
C2 C7 1.376(4) . ?
C3 C4 1.377(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.381(3) . ?
C5 N1 1.407(2) . ?
C6 C7 1.371(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
N1 C10 1.366(2) . ?
N1 C8 1.469(2) . ?
C8 C9 1.507(2) . ?
C8 C11 1.518(2) . ?
C8 H8 0.9800 . ?
C9 O2 1.206(2) . ?
C9 N2 1.355(2) . ?
N2 O3 1.3747(19) . ?
N2 C10 1.396(2) . ?
C10 O1 1.202(2) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 O3 1.454(2) . ?
C12 C13 1.489(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.380(3) . ?
C13 C18 1.381(3) . ?
C14 C15 1.374(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.366(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.368(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.379(4) . ?
C17 H17 0.9300 . ?
C18 H18 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
F1 C1 F2 109.6(7) . . ?
F3' C1 F1' 108.2(7) . . ?
F3' C1 F2' 108.6(6) . . ?
F1' C1 F2' 103.8(6) . . ?
F1 C1 F3 106.7(7) . . ?
F2 C1 F3 104.5(6) . . ?
F1 C1 C2 110.9(7) . . ?
F3' C1 C2 111.8(6) . . ?
F2 C1 C2 114.2(6) . . ?
F1' C1 C2 112.7(5) . . ?
F2' C1 C2 111.3(5) . . ?
F3 C1 C2 110.5(6) . . ?
C3 C2 C7 118.7(2) . . ?
C3 C2 C1 121.2(3) . . ?
C7 C2 C1 120.0(3) . . ?
C2 C3 C4 120.7(2) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C5 120.3(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 119.08(18) . . ?
C4 C5 N1 119.82(16) . . ?
C6 C5 N1 121.09(16) . . ?
C7 C6 C5 119.9(2) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C7 C2 121.3(2) . . ?
C6 C7 H7 119.3 . . ?
C2 C7 H7 119.3 . . ?
C10 N1 C5 125.20(14) . . ?
C10 N1 C8 111.29(13) . . ?
C5 N1 C8 123.24(13) . . ?
N1 C8 C9 103.42(13) . . ?
N1 C8 C11 112.82(14) . . ?
C9 C8 C11 110.98(14) . . ?
N1 C8 H8 109.8 . . ?
C9 C8 H8 109.8 . . ?
C11 C8 H8 109.8 . . ?
O2 C9 N2 127.68(17) . . ?
O2 C9 C8 127.63(16) . . ?
N2 C9 C8 104.65(14) . . ?
C9 N2 O3 123.36(14) . . ?
C9 N2 C10 115.30(14) . . ?
O3 N2 C10 121.34(14) . . ?
O1 C10 N1 130.29(16) . . ?
O1 C10 N2 124.44(16) . . ?
N1 C10 N2 105.24(14) . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O3 C12 C13 108.40(15) . . ?
O3 C12 H12A 110.0 . . ?
C13 C12 H12A 110.0 . . ?
O3 C12 H12B 110.0 . . ?
C13 C12 H12B 110.0 . . ?
H12A C12 H12B 108.4 . . ?
C14 C13 C18 118.9(2) . . ?
C14 C13 C12 121.34(17) . . ?
C18 C13 C12 119.8(2) . . ?
C15 C14 C13 120.3(2) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C16 C15 C14 120.6(3) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C17 119.6(3) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C16 C17 C18 120.4(2) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C17 C18 C13 120.2(3) . . ?
C17 C18 H18 119.9 . . ?
C13 C18 H18 119.9 . . ?
N2 O3 C12 110.24(13) . . ?

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 60.2(11) . . . . ?
F3' C1 C2 C3 -99.6(10) . . . . ?
F2 C1 C2 C3 -175.4(8) . . . . ?
F1' C1 C2 C3 22.6(8) . . . . ?
F2' C1 C2 C3 138.8(8) . . . . ?
F3 C1 C2 C3 -58.0(8) . . . . ?
F1 C1 C2 C7 -122.9(10) . . . . ?
F3' C1 C2 C7 77.4(10) . . . . ?
F2 C1 C2 C7 1.5(9) . . . . ?
F1' C1 C2 C7 -160.5(7) . . . . ?
F2' C1 C2 C7 -44.3(8) . . . . ?
F3 C1 C2 C7 119.0(8) . . . . ?
C7 C2 C3 C4 1.5(5) . . . . ?
C1 C2 C3 C4 178.4(3) . . . . ?
C2 C3 C4 C5 -1.1(4) . . . . ?
C3 C4 C5 C6 1.0(4) . . . . ?
C3 C4 C5 N1 -179.0(2) . . . . ?
C4 C5 C6 C7 -1.2(3) . . . . ?
N1 C5 C6 C7 178.7(2) . . . . ?
C5 C6 C7 C2 1.6(4) . . . . ?
C3 C2 C7 C6 -1.7(4) . . . . ?
C1 C2 C7 C6 -178.7(3) . . . . ?
C4 C5 N1 C10 155.54(18) . . . . ?
C6 C5 N1 C10 -24.4(3) . . . . ?
C4 C5 N1 C8 -18.0(3) . . . . ?
C6 C5 N1 C8 162.08(17) . . . . ?
C10 N1 C8 C9 -3.33(17) . . . . ?
C5 N1 C8 C9 170.99(14) . . . . ?
C10 N1 C8 C11 116.65(16) . . . . ?
C5 N1 C8 C11 -69.0(2) . . . . ?
N1 C8 C9 O2 -179.25(16) . . . . ?
C11 C8 C9 O2 59.5(2) . . . . ?
N1 C8 C9 N2 2.58(16) . . . . ?
C11 C8 C9 N2 -118.65(15) . . . . ?
O2 C9 N2 O3 0.2(3) . . . . ?
C8 C9 N2 O3 178.35(13) . . . . ?
O2 C9 N2 C10 -179.32(16) . . . . ?
C8 C9 N2 C10 -1.16(19) . . . . ?
C5 N1 C10 O1 6.4(3) . . . . ?
C8 N1 C10 O1 -179.37(16) . . . . ?
C5 N1 C10 N2 -171.50(14) . . . . ?
C8 N1 C10 N2 2.69(17) . . . . ?
C9 N2 C10 O1 -179.00(15) . . . . ?
O3 N2 C10 O1 1.5(2) . . . . ?
C9 N2 C10 N1 -0.91(19) . . . . ?
O3 N2 C10 N1 179.57(13) . . . . ?
O3 C12 C13 C14 43.5(2) . . . . ?
O3 C12 C13 C18 -138.37(18) . . . . ?
C18 C13 C14 C15 0.2(3) . . . . ?
C12 C13 C14 C15 178.4(2) . . . . ?
C13 C14 C15 C16 0.4(4) . . . . ?
C14 C15 C16 C17 -0.9(4) . . . . ?
C15 C16 C17 C18 0.7(4) . . . . ?
C16 C17 C18 C13 0.0(4) . . . . ?
C14 C13 C18 C17 -0.4(3) . . . . ?
C12 C13 C18 C17 -178.6(2) . . . . ?
C9 N2 O3 C12 103.83(18) . . . . ?
C10 N2 O3 C12 -76.69(18) . . . . ?
C13 C12 O3 N2 -149.70(15) . . . . ?

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
C11 H11B O2 0.96 2.65 3.602(2) 171.1 3
C11 H11A O1 0.96 2.61 3.461(2) 147.4 1_565
C6 H6 O1 0.93 2.33 2.899(2) 119.0 .

_refine_diff_density_max         0.291
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.050

