# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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 1472053'
_audit_update_record             
;
2016-04-03 deposited with the CCDC.
2016-05-31 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         'C19 H10 F3 N O2'
_chemical_formula_sum            'C19 H10 F3 N O2'
_chemical_formula_weight         341.28

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      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                   5.8910(5)
_cell_length_b                   7.7688(6)
_cell_length_c                   16.6580(14)
_cell_angle_alpha                84.298(6)
_cell_angle_beta                 82.177(7)
_cell_angle_gamma                84.893(6)
_cell_volume                     749.33(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    293
_cell_measurement_reflns_used    4848
_cell_measurement_theta_min      3.5
_cell_measurement_theta_max      32.5

_exptl_crystal_description       block
_exptl_crystal_colour            color
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_F_000             348
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.124
_shelx_estimated_absorpt_T_min   0.960
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.89947
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   SCALE3
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0938
_diffrn_reflns_number            7945
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.460
_diffrn_reflns_theta_max         32.461
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.897
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.897
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.897
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4848
_reflns_number_gt                2632
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1041P)²+0.2167P] 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         4848
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1308
_refine_ls_R_factor_gt           0.0734
_refine_ls_wR_factor_ref         0.2390
_refine_ls_wR_factor_gt          0.1927
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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
O2 O 1.4684(3) 0.0423(2) -0.11831(11) 0.0596(5) Uani 1 1 d . . . . .
N1 N 0.7447(3) 0.3586(3) -0.05919(12) 0.0463(5) Uani 1 1 d . . . . .
C10 C 1.1166(3) 0.1997(3) -0.06265(13) 0.0369(5) Uani 1 1 d . . . . .
O1 O 1.2040(4) 0.1268(3) -0.42180(12) 0.0772(7) Uani 1 1 d . . . . .
C7 C 0.9262(3) 0.2836(3) 0.06475(13) 0.0357(4) Uani 1 1 d . . . . .
C12 C 0.9680(4) 0.2560(3) -0.18758(14) 0.0397(5) Uani 1 1 d . . . . .
C13 C 1.1839(4) 0.1659(3) -0.20435(14) 0.0404(5) Uani 1 1 d . . . . .
F2 F 1.3638(5) 0.1679(4) -0.54421(12) 0.1299(10) Uani 1 1 d . . . . .
C11 C 0.9282(3) 0.2780(3) -0.09931(13) 0.0376(5) Uani 1 1 d . . . . .
C14 C 1.2868(4) 0.1238(3) -0.12674(14) 0.0420(5) Uani 1 1 d . . . . .
C6 C 0.9098(4) 0.2913(3) 0.15441(13) 0.0385(5) Uani 1 1 d . . . . .
C15 C 1.2681(4) 0.1247(3) -0.28217(15) 0.0489(6) Uani 1 1 d . . . . .
H15 H 1.4106 0.0643 -0.2935 0.059 Uiso 1 1 calc R U . . .
C8 C 0.7501(4) 0.3599(3) 0.02153(14) 0.0446(5) Uani 1 1 d . . . . .
H8 H 0.6253 0.4168 0.0511 0.054 Uiso 1 1 calc R U . . .
C9 C 1.1169(4) 0.2011(3) 0.01966(13) 0.0398(5) Uani 1 1 d . . . . .
H9 H 1.2400 0.1489 0.0449 0.048 Uiso 1 1 calc R U . . .
F1 F 1.1889(7) 0.3795(4) -0.49015(19) 0.1687(16) Uani 1 1 d . . . . .
C3 C 0.8811(5) 0.3009(4) 0.32346(17) 0.0594(7) Uani 1 1 d . . . . .
H3 H 0.8714 0.3039 0.3795 0.071 Uiso 1 1 calc R U . . .
C5 C 0.7114(5) 0.3583(4) 0.20000(16) 0.0575(7) Uani 1 1 d . . . . .
H5 H 0.5854 0.4010 0.1739 0.069 Uiso 1 1 calc R U . . .
C16 C 1.1312(5) 0.1772(3) -0.34232(15) 0.0542(6) Uani 1 1 d . . . . .
C1 C 1.0931(4) 0.2300(4) 0.19636(15) 0.0533(6) Uani 1 1 d . . . . .
H1 H 1.2285 0.1848 0.1679 0.064 Uiso 1 1 calc R U . . .
C18 C 0.8336(4) 0.3044(4) -0.24850(15) 0.0529(6) Uani 1 1 d . . . . .
H18 H 0.6898 0.3632 -0.2374 0.063 Uiso 1 1 calc R U . . .
C4 C 0.6983(5) 0.3624(4) 0.28323(17) 0.0649(8) Uani 1 1 d . . . . .
H4 H 0.5638 0.4075 0.3123 0.078 Uiso 1 1 calc R U . . .
C2 C 1.0780(5) 0.2350(4) 0.28001(17) 0.0622(7) Uani 1 1 d . . . . .
H2 H 1.2030 0.1932 0.3068 0.075 Uiso 1 1 calc R U . . .
C17 C 0.9172(5) 0.2636(4) -0.32705(16) 0.0598(7) Uani 1 1 d . . . . .
H17 H 0.8289 0.2945 -0.3692 0.072 Uiso 1 1 calc R U . . .
F3 F 1.4988(6) 0.2742(7) -0.45302(18) 0.1920(19) Uani 1 1 d . . . . .
C19 C 1.3083(7) 0.2375(6) -0.4756(2) 0.0895(12) 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
O2 C14 1.211(3) . ?
N1 C11 1.332(3) . ?
N1 C8 1.350(3) . ?
C10 C9 1.372(3) . ?
C10 C11 1.402(3) . ?
C10 C14 1.490(3) . ?
O1 C19 1.308(5) . ?
O1 C16 1.417(3) . ?
C7 C8 1.398(3) . ?
C7 C9 1.405(3) . ?
C7 C6 1.490(3) . ?
C12 C18 1.374(3) . ?
C12 C13 1.404(3) . ?
C12 C11 1.482(3) . ?
C13 C15 1.381(3) . ?
C13 C14 1.497(3) . ?
F2 C19 1.302(4) . ?
C6 C1 1.389(3) . ?
C6 C5 1.394(3) . ?
C15 C16 1.379(4) . ?
C15 H15 0.9300 . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
F1 C19 1.275(4) . ?
C3 C2 1.368(4) . ?
C3 C4 1.371(4) . ?
C3 H3 0.9300 . ?
C5 C4 1.382(4) . ?
C5 H5 0.9300 . ?
C16 C17 1.379(4) . ?
C1 C2 1.388(4) . ?
C1 H1 0.9300 . ?
C18 C17 1.391(4) . ?
C18 H18 0.9300 . ?
C4 H4 0.9300 . ?
C2 H2 0.9300 . ?
C17 H17 0.9300 . ?
F3 C19 1.294(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
C11 N1 C8 115.04(19) . . ?
C9 C10 C11 119.86(18) . . ?
C9 C10 C14 131.78(19) . . ?
C11 C10 C14 108.35(19) . . ?
C19 O1 C16 118.5(3) . . ?
C8 C7 C9 116.9(2) . . ?
C8 C7 C6 120.84(18) . . ?
C9 C7 C6 122.29(18) . . ?
C18 C12 C13 120.6(2) . . ?
C18 C12 C11 131.6(2) . . ?
C13 C12 C11 107.86(19) . . ?
C15 C13 C12 121.2(2) . . ?
C15 C13 C14 129.7(2) . . ?
C12 C13 C14 109.01(19) . . ?
N1 C11 C10 124.0(2) . . ?
N1 C11 C12 126.68(19) . . ?
C10 C11 C12 109.34(17) . . ?
O2 C14 C10 127.8(2) . . ?
O2 C14 C13 126.8(2) . . ?
C10 C14 C13 105.41(17) . . ?
C1 C6 C5 117.0(2) . . ?
C1 C6 C7 120.95(19) . . ?
C5 C6 C7 122.0(2) . . ?
C16 C15 C13 117.0(2) . . ?
C16 C15 H15 121.5 . . ?
C13 C15 H15 121.5 . . ?
N1 C8 C7 126.0(2) . . ?
N1 C8 H8 117.0 . . ?
C7 C8 H8 117.0 . . ?
C10 C9 C7 118.27(19) . . ?
C10 C9 H9 120.9 . . ?
C7 C9 H9 120.9 . . ?
C2 C3 C4 119.1(3) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C4 C5 C6 121.2(2) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C15 C16 C17 122.8(2) . . ?
C15 C16 O1 118.7(2) . . ?
C17 C16 O1 118.3(2) . . ?
C2 C1 C6 121.2(2) . . ?
C2 C1 H1 119.4 . . ?
C6 C1 H1 119.4 . . ?
C12 C18 C17 118.6(2) . . ?
C12 C18 H18 120.7 . . ?
C17 C18 H18 120.7 . . ?
C3 C4 C5 120.8(2) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C3 C2 C1 120.7(3) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C16 C17 C18 119.9(2) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
F1 C19 F3 108.1(5) . . ?
F1 C19 F2 107.4(3) . . ?
F3 C19 F2 106.3(4) . . ?
F1 C19 O1 114.3(4) . . ?
F3 C19 O1 110.8(3) . . ?
F2 C19 O1 109.6(4) . . ?

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
C18 C12 C13 C15 0.5(3) . . . . ?
C11 C12 C13 C15 179.4(2) . . . . ?
C18 C12 C13 C14 -177.6(2) . . . . ?
C11 C12 C13 C14 1.3(2) . . . . ?
C8 N1 C11 C10 -0.3(3) . . . . ?
C8 N1 C11 C12 179.7(2) . . . . ?
C9 C10 C11 N1 1.1(3) . . . . ?
C14 C10 C11 N1 -179.9(2) . . . . ?
C9 C10 C11 C12 -178.95(19) . . . . ?
C14 C10 C11 C12 0.1(2) . . . . ?
C18 C12 C11 N1 -2.1(4) . . . . ?
C13 C12 C11 N1 179.1(2) . . . . ?
C18 C12 C11 C10 177.9(2) . . . . ?
C13 C12 C11 C10 -0.9(2) . . . . ?
C9 C10 C14 O2 0.8(4) . . . . ?
C11 C10 C14 O2 -178.1(2) . . . . ?
C9 C10 C14 C13 179.6(2) . . . . ?
C11 C10 C14 C13 0.7(2) . . . . ?
C15 C13 C14 O2 -0.4(4) . . . . ?
C12 C13 C14 O2 177.6(2) . . . . ?
C15 C13 C14 C10 -179.2(2) . . . . ?
C12 C13 C14 C10 -1.2(2) . . . . ?
C8 C7 C6 C1 -174.0(2) . . . . ?
C9 C7 C6 C1 5.8(3) . . . . ?
C8 C7 C6 C5 6.6(3) . . . . ?
C9 C7 C6 C5 -173.6(2) . . . . ?
C12 C13 C15 C16 0.5(3) . . . . ?
C14 C13 C15 C16 178.2(2) . . . . ?
C11 N1 C8 C7 -0.9(4) . . . . ?
C9 C7 C8 N1 1.4(4) . . . . ?
C6 C7 C8 N1 -178.8(2) . . . . ?
C11 C10 C9 C7 -0.6(3) . . . . ?
C14 C10 C9 C7 -179.4(2) . . . . ?
C8 C7 C9 C10 -0.5(3) . . . . ?
C6 C7 C9 C10 179.68(19) . . . . ?
C1 C6 C5 C4 -0.3(4) . . . . ?
C7 C6 C5 C4 179.2(2) . . . . ?
C13 C15 C16 C17 -1.4(4) . . . . ?
C13 C15 C16 O1 -175.6(2) . . . . ?
C19 O1 C16 C15 -98.0(3) . . . . ?
C19 O1 C16 C17 87.6(4) . . . . ?
C5 C6 C1 C2 0.2(4) . . . . ?
C7 C6 C1 C2 -179.3(2) . . . . ?
C13 C12 C18 C17 -0.6(4) . . . . ?
C11 C12 C18 C17 -179.2(2) . . . . ?
C2 C3 C4 C5 0.0(5) . . . . ?
C6 C5 C4 C3 0.2(5) . . . . ?
C4 C3 C2 C1 -0.1(5) . . . . ?
C6 C1 C2 C3 0.0(5) . . . . ?
C15 C16 C17 C18 1.4(4) . . . . ?
O1 C16 C17 C18 175.6(3) . . . . ?
C12 C18 C17 C16 -0.3(4) . . . . ?
C16 O1 C19 F1 -60.0(5) . . . . ?
C16 O1 C19 F3 62.4(4) . . . . ?
C16 O1 C19 F2 179.4(3) . . . . ?

_refine_diff_density_max         0.417
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.055

