# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2017

####################################################################### 
# 
# 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 1516018'
_audit_update_record             
;
2016-11-09 deposited with the CCDC.
2017-06-13 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 H11 Cl F3 N O'
_chemical_formula_sum            'C19 H11 Cl F3 N O'
_chemical_formula_weight         361.74

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   17.5265(8)
_cell_length_b                   18.9585(9)
_cell_length_c                   11.1154(5)
_cell_angle_alpha                90
_cell_angle_beta                 120.995(2)
_cell_angle_gamma                90
_cell_volume                     3166.0(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3960
_cell_measurement_theta_min      2.7
_cell_measurement_theta_max      28.3

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_F_000             1472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.13
_exptl_absorpt_coefficient_mu    0.280
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6865
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_measurement_method       Omega-Scan
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            51891
_diffrn_reflns_av_unetI/netI     0.0158
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.711
_diffrn_reflns_theta_max         28.332
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3960
_reflns_number_gt                3027
_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       'APEX2 (Bruker, 2010)'
_computing_cell_refinement       'APEX2 (Bruker, 2010); SAINT (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009);XPREP(Sheldrick,2008)'
_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)+(0.0559P)²+2.2774P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    refU
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3960
_refine_ls_number_parameters     295
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.1244
_refine_ls_wR_factor_gt          0.1131
_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
Cl1 Cl 0.93016(4) 0.64302(2) 0.52979(7) 0.06920(19) Uani 1 1 d . . . . .
O1 O 0.81962(9) 0.20255(6) 0.40542(13) 0.0514(3) Uani 1 1 d . . . . .
N1 N 0.88597(9) 0.37911(7) 0.52734(14) 0.0410(3) Uani 1 1 d . . . . .
C1 C 0.87494(10) 0.43768(8) 0.44830(17) 0.0396(3) Uani 1 1 d . . . . .
C2 C 0.90622(12) 0.50286(10) 0.51822(19) 0.0456(4) Uani 1 1 d . . . . .
H2 H 0.9358 0.5047 0.6157 0.056(6) Uani 1 1 calc R . . . .
C11 C 0.85657(10) 0.31982(8) 0.45643(16) 0.0386(3) Uani 1 1 d . . . . .
C6 C 0.83272(11) 0.43603(9) 0.29930(17) 0.0419(4) Uani 1 1 d . . . . .
C8 C 0.81809(10) 0.31257(8) 0.31046(17) 0.0406(3) Uani 1 1 d . . . . .
C3 C 0.89300(12) 0.56289(9) 0.4430(2) 0.0490(4) Uani 1 1 d . . . . .
C12 C 0.85748(10) 0.25080(8) 0.51518(17) 0.0408(3) Uani 1 1 d . . . . .
C7 C 0.80459(12) 0.37040(9) 0.23004(19) 0.0446(4) Uani 1 1 d . . . . .
H7 H 0.7778 0.3670 0.1331 0.057(6) Uani 1 1 calc R . . . .
C13 C 0.88700(12) 0.23390(10) 0.6481(2) 0.0433(4) Uani 1 1 d . . . . .
C4 C 0.84911(14) 0.56264(10) 0.2955(2) 0.0544(5) Uani 1 1 d . . . . .
H4 H 0.8399 0.6044 0.2460 0.060(6) Uani 1 1 calc R . . . .
C9 C 0.79760(12) 0.23616(9) 0.27577(18) 0.0463(4) Uani 1 1 d . . . . .
H9 H 0.7342 0.2300 0.2067 0.046(5) Uani 1 1 calc R . . . .
C14 C 0.88990(10) 0.16579(9) 0.71108(18) 0.0437(4) Uani 1 1 d . . . . .
C5 C 0.82047(13) 0.50020(10) 0.2268(2) 0.0513(4) Uani 1 1 d . . . . .
H5 H 0.7920 0.4996 0.1294 0.066(6) Uani 1 1 calc R . . . .
C10 C 0.85306(14) 0.20171(9) 0.22419(19) 0.0530(4) Uani 1 1 d . . . . .
C19 C 0.92107(13) 0.16275(11) 0.8540(2) 0.0529(5) Uani 1 1 d . . . . .
H19 H 0.9387 0.2041 0.9064 0.071(7) Uani 1 1 calc R . . . .
C15 C 0.86432(14) 0.10243(11) 0.6358(2) 0.0579(5) Uani 1 1 d . . . . .
H15 H 0.8432 0.1026 0.5400 0.069(7) Uani 1 1 calc R . . . .
C18 C 0.92644(14) 0.09974(13) 0.9200(2) 0.0639(6) Uani 1 1 d . . . . .
H18 H 0.9471 0.0991 1.0157 0.072(7) Uani 1 1 calc R . . . .
C16 C 0.87022(17) 0.03972(11) 0.7028(3) 0.0692(6) Uani 1 1 d . . . . .
H16 H 0.8530 -0.0020 0.6514 0.095(9) Uani 1 1 calc R . . . .
C17 C 0.90119(14) 0.03780(12) 0.8445(3) 0.0681(6) Uani 1 1 d . . . . .
H17 H 0.9050 -0.0048 0.8886 0.089(8) Uani 1 1 calc R . . . .
F2 F 0.83580(10) 0.22897(7) 0.10250(12) 0.0756(4) Uani 1 1 d . . . . .
F1 F 0.83718(12) 0.13315(6) 0.20375(18) 0.0911(5) Uani 1 1 d . . . . .
F3 F 0.93942(8) 0.20989(7) 0.31280(13) 0.0745(4) Uani 1 1 d . . . . .
H13 H 0.9106(12) 0.2717(11) 0.7089(18) 0.047(5) 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
Cl1 C3 1.7367(18) . ?
O1 C12 1.390(2) . ?
O1 C9 1.435(2) . ?
N1 C11 1.316(2) . ?
N1 C1 1.366(2) . ?
C1 C2 1.412(2) . ?
C1 C6 1.425(2) . ?
C2 C3 1.360(2) . ?
C2 H2 0.9300 . ?
C11 C8 1.407(2) . ?
C11 C12 1.459(2) . ?
C6 C7 1.412(2) . ?
C6 C5 1.413(2) . ?
C8 C7 1.356(2) . ?
C8 C9 1.494(2) . ?
C3 C4 1.408(3) . ?
C12 C13 1.329(2) . ?
C7 H7 0.9300 . ?
C13 C14 1.457(2) . ?
C13 H13 0.92(2) . ?
C4 C5 1.357(3) . ?
C4 H4 0.9300 . ?
C9 C10 1.508(3) . ?
C9 H9 0.9800 . ?
C14 C19 1.390(3) . ?
C14 C15 1.399(3) . ?
C5 H5 0.9300 . ?
C10 F3 1.323(2) . ?
C10 F1 1.324(2) . ?
C10 F2 1.329(2) . ?
C19 C18 1.379(3) . ?
C19 H19 0.9300 . ?
C15 C16 1.378(3) . ?
C15 H15 0.9300 . ?
C18 C17 1.377(3) . ?
C18 H18 0.9300 . ?
C16 C17 1.377(3) . ?
C16 H16 0.9300 . ?
C17 H17 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
C12 O1 C9 110.44(12) . . ?
C11 N1 C1 115.27(13) . . ?
N1 C1 C2 118.11(14) . . ?
N1 C1 C6 123.12(14) . . ?
C2 C1 C6 118.77(15) . . ?
C3 C2 C1 119.95(16) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
N1 C11 C8 125.55(14) . . ?
N1 C11 C12 125.97(14) . . ?
C8 C11 C12 108.48(14) . . ?
C7 C6 C5 122.67(16) . . ?
C7 C6 C1 118.68(15) . . ?
C5 C6 C1 118.65(15) . . ?
C7 C8 C11 119.90(15) . . ?
C7 C8 C9 132.57(15) . . ?
C11 C8 C9 107.52(14) . . ?
C2 C3 C4 122.11(17) . . ?
C2 C3 Cl1 119.61(15) . . ?
C4 C3 Cl1 118.28(14) . . ?
C13 C12 O1 123.63(15) . . ?
C13 C12 C11 128.48(15) . . ?
O1 C12 C11 107.89(13) . . ?
C8 C7 C6 117.37(15) . . ?
C8 C7 H7 121.3 . . ?
C6 C7 H7 121.3 . . ?
C12 C13 C14 130.16(17) . . ?
C12 C13 H13 113.4(10) . . ?
C14 C13 H13 116.4(10) . . ?
C5 C4 C3 118.70(17) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
O1 C9 C8 105.47(13) . . ?
O1 C9 C10 107.27(14) . . ?
C8 C9 C10 113.67(15) . . ?
O1 C9 H9 110.1 . . ?
C8 C9 H9 110.1 . . ?
C10 C9 H9 110.1 . . ?
C19 C14 C15 117.66(17) . . ?
C19 C14 C13 118.79(17) . . ?
C15 C14 C13 123.54(17) . . ?
C4 C5 C6 121.78(18) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
F3 C10 F1 107.56(17) . . ?
F3 C10 F2 106.60(17) . . ?
F1 C10 F2 106.83(16) . . ?
F3 C10 C9 112.37(15) . . ?
F1 C10 C9 111.75(17) . . ?
F2 C10 C9 111.41(15) . . ?
C18 C19 C14 121.5(2) . . ?
C18 C19 H19 119.2 . . ?
C14 C19 H19 119.2 . . ?
C16 C15 C14 120.4(2) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C17 C18 C19 120.1(2) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C17 C16 C15 121.1(2) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C16 C17 C18 119.2(2) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 H17 120.4 . . ?

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
C11 N1 C1 C2 -179.11(14) . . . . ?
C11 N1 C1 C6 1.5(2) . . . . ?
N1 C1 C2 C3 -177.07(15) . . . . ?
C6 C1 C2 C3 2.3(2) . . . . ?
C1 N1 C11 C8 1.7(2) . . . . ?
C1 N1 C11 C12 -177.61(14) . . . . ?
N1 C1 C6 C7 -3.1(2) . . . . ?
C2 C1 C6 C7 177.57(15) . . . . ?
N1 C1 C6 C5 176.73(15) . . . . ?
C2 C1 C6 C5 -2.6(2) . . . . ?
N1 C11 C8 C7 -3.5(3) . . . . ?
C12 C11 C8 C7 175.96(15) . . . . ?
N1 C11 C8 C9 177.94(15) . . . . ?
C12 C11 C8 C9 -2.60(18) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
C1 C2 C3 Cl1 178.98(13) . . . . ?
C9 O1 C12 C13 -177.78(16) . . . . ?
C9 O1 C12 C11 3.05(17) . . . . ?
N1 C11 C12 C13 0.2(3) . . . . ?
C8 C11 C12 C13 -179.29(17) . . . . ?
N1 C11 C12 O1 179.27(14) . . . . ?
C8 C11 C12 O1 -0.18(17) . . . . ?
C11 C8 C7 C6 1.7(2) . . . . ?
C9 C8 C7 C6 179.83(17) . . . . ?
C5 C6 C7 C8 -178.51(16) . . . . ?
C1 C6 C7 C8 1.3(2) . . . . ?
O1 C12 C13 C14 1.7(3) . . . . ?
C11 C12 C13 C14 -179.31(16) . . . . ?
C2 C3 C4 C5 -1.1(3) . . . . ?
Cl1 C3 C4 C5 179.48(14) . . . . ?
C12 O1 C9 C8 -4.55(18) . . . . ?
C12 O1 C9 C10 116.94(15) . . . . ?
C7 C8 C9 O1 -173.98(17) . . . . ?
C11 C8 C9 O1 4.33(18) . . . . ?
C7 C8 C9 C10 68.8(2) . . . . ?
C11 C8 C9 C10 -112.90(16) . . . . ?
C12 C13 C14 C19 -177.29(18) . . . . ?
C12 C13 C14 C15 3.8(3) . . . . ?
C3 C4 C5 C6 0.7(3) . . . . ?
C7 C6 C5 C4 -179.06(17) . . . . ?
C1 C6 C5 C4 1.1(3) . . . . ?
O1 C9 C10 F3 -61.48(19) . . . . ?
C8 C9 C10 F3 54.7(2) . . . . ?
O1 C9 C10 F1 59.5(2) . . . . ?
C8 C9 C10 F1 175.73(16) . . . . ?
O1 C9 C10 F2 178.97(14) . . . . ?
C8 C9 C10 F2 -64.8(2) . . . . ?
C15 C14 C19 C18 -0.3(3) . . . . ?
C13 C14 C19 C18 -179.19(18) . . . . ?
C19 C14 C15 C16 0.0(3) . . . . ?
C13 C14 C15 C16 178.9(2) . . . . ?
C14 C19 C18 C17 0.4(3) . . . . ?
C14 C15 C16 C17 0.0(4) . . . . ?
C15 C16 C17 C18 0.1(4) . . . . ?
C19 C18 C17 C16 -0.4(3) . . . . ?

_refine_diff_density_max         0.234
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.041



