# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_20160506lmf2_0m_a_a
_database_code_depnum_ccdc_archive 'CCDC 1478785'
_audit_update_record             
;
2016-05-09 deposited with the CCDC.
2016-08-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H10 Cl F3 N2 O'
_chemical_formula_weight         350.72

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'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   8.165(2)
_cell_length_b                   9.432(2)
_cell_length_c                   10.126(3)
_cell_angle_alpha                85.485(7)
_cell_angle_beta                 83.241(8)
_cell_angle_gamma                73.145(7)
_cell_volume                     740.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3407
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      27.88

_exptl_crystal_description       scheet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             356
_exptl_absorpt_coefficient_mu    0.299
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9210
_exptl_absorpt_correction_T_max  0.9940
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6400
_diffrn_reflns_av_R_equivalents  0.0612
_diffrn_reflns_av_sigmaI/netI    0.0872
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.26
_diffrn_reflns_theta_max         27.95
_reflns_number_total             3470
_reflns_number_gt                2752
_reflns_threshold_expression     >2sigma(I)

_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 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0797P)²+0.4099P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3470
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0787
_refine_ls_R_factor_gt           0.0630
_refine_ls_wR_factor_ref         0.1787
_refine_ls_wR_factor_gt          0.1666
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5595(3) 0.6027(2) 0.2364(2) 0.0283(5) Uani 1 1 d . . .
H1 H 0.5339 0.6945 0.2737 0.034 Uiso 1 1 calc R . .
C2 C 0.6808(3) 0.5703(3) 0.1267(2) 0.0305(5) Uani 1 1 d . . .
H2 H 0.7366 0.6395 0.0903 0.037 Uiso 1 1 calc R . .
C3 C 0.7173(3) 0.4330(3) 0.0725(2) 0.0284(5) Uani 1 1 d . . .
C4 C 0.6372(3) 0.3279(3) 0.1244(3) 0.0313(5) Uani 1 1 d . . .
H4 H 0.6633 0.2364 0.0864 0.038 Uiso 1 1 calc R . .
C5 C 0.5171(3) 0.3612(2) 0.2342(2) 0.0289(5) Uani 1 1 d . . .
H5 H 0.4630 0.2908 0.2707 0.035 Uiso 1 1 calc R . .
C6 C 0.4757(3) 0.4994(2) 0.2912(2) 0.0247(5) Uani 1 1 d . . .
C7 C 0.3409(3) 0.5250(2) 0.4083(2) 0.0257(5) Uani 1 1 d . . .
C8 C 0.1700(3) 0.7212(2) 0.5608(2) 0.0236(5) Uani 1 1 d . . .
C9 C 0.0577(3) 0.6498(2) 0.6272(2) 0.0266(5) Uani 1 1 d . . .
H9 H 0.0640 0.5539 0.6068 0.032 Uiso 1 1 calc R . .
C10 C -0.0676(3) 0.7233(2) 0.7271(2) 0.0269(5) Uani 1 1 d . . .
H10 H -0.1434 0.6744 0.7714 0.032 Uiso 1 1 calc R . .
C11 C -0.0803(3) 0.8643(2) 0.7601(2) 0.0258(5) Uani 1 1 d . . .
C12 C 0.0355(3) 0.9412(2) 0.6949(2) 0.0237(5) Uani 1 1 d . . .
C13 C 0.0354(3) 1.0869(2) 0.7213(2) 0.0288(5) Uani 1 1 d . . .
H13 H -0.0436 1.1392 0.7867 0.035 Uiso 1 1 calc R . .
C14 C 0.1508(3) 1.1499(2) 0.6507(3) 0.0324(5) Uani 1 1 d . . .
H14 H 0.1510 1.2455 0.6670 0.039 Uiso 1 1 calc R . .
C15 C 0.2701(3) 1.0684(3) 0.5524(3) 0.0311(5) Uani 1 1 d . . .
H15 H 0.3481 1.1129 0.5047 0.037 Uiso 1 1 calc R . .
C16 C 0.1610(3) 0.8688(2) 0.5940(2) 0.0227(4) Uani 1 1 d . . .
C17 C -0.2234(3) 0.9396(2) 0.8664(2) 0.0298(5) Uani 1 1 d . . .
Cl1 Cl 0.86930(9) 0.39259(7) -0.06565(6) 0.0394(2) Uani 1 1 d . . .
F1 F -0.3226(2) 0.85461(18) 0.90942(17) 0.0493(5) Uani 1 1 d . . .
F2 F -0.3219(2) 1.06659(18) 0.81777(17) 0.0494(5) Uani 1 1 d . . .
F3 F -0.1575(2) 0.9714(2) 0.97002(16) 0.0487(5) Uani 1 1 d . . .
N1 N 0.2942(2) 0.6644(2) 0.4565(2) 0.0263(4) Uani 1 1 d . . .
H1A H 0.3575 0.7215 0.4361 0.032 Uiso 1 1 d R . .
N2 N 0.2769(2) 0.9324(2) 0.5246(2) 0.0267(4) Uani 1 1 d . . .
O1 O 0.2774(2) 0.42758(18) 0.45547(19) 0.0369(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
C1 C2 1.388(3) . ?
C1 C6 1.391(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.384(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(3) . ?
C3 Cl1 1.745(2) . ?
C4 C5 1.384(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.401(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.504(3) . ?
C7 O1 1.220(3) . ?
C7 N1 1.371(3) . ?
C8 C9 1.373(3) . ?
C8 N1 1.398(3) . ?
C8 C16 1.437(3) . ?
C9 C10 1.416(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.368(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.425(3) . ?
C11 C17 1.540(3) . ?
C12 C13 1.420(3) . ?
C12 C16 1.421(3) . ?
C13 C14 1.361(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.409(3) . ?
C14 H14 0.9300 . ?
C15 N2 1.319(3) . ?
C15 H15 0.9300 . ?
C16 N2 1.362(3) . ?
C17 F1 1.314(3) . ?
C17 F3 1.325(3) . ?
C17 F2 1.329(3) . ?
N1 H1A 0.8476 . ?

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
C2 C1 C6 120.83(19) . . ?
C2 C1 H1 119.6 . . ?
C6 C1 H1 119.6 . . ?
C3 C2 C1 118.8(2) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C4 C3 C2 122.0(2) . . ?
C4 C3 Cl1 119.29(17) . . ?
C2 C3 Cl1 118.74(19) . . ?
C3 C4 C5 118.73(19) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C4 C5 C6 120.9(2) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 118.8(2) . . ?
C1 C6 C7 124.74(18) . . ?
C5 C6 C7 116.50(19) . . ?
O1 C7 N1 123.0(2) . . ?
O1 C7 C6 121.61(18) . . ?
N1 C7 C6 115.40(19) . . ?
C9 C8 N1 125.46(19) . . ?
C9 C8 C16 119.99(19) . . ?
N1 C8 C16 114.52(18) . . ?
C8 C9 C10 119.56(19) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C11 C10 C9 121.8(2) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C10 C11 C12 120.30(19) . . ?
C10 C11 C17 119.1(2) . . ?
C12 C11 C17 120.55(18) . . ?
C13 C12 C16 116.4(2) . . ?
C13 C12 C11 125.32(19) . . ?
C16 C12 C11 118.28(18) . . ?
C14 C13 C12 120.0(2) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 119.2(2) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
N2 C15 C14 123.4(2) . . ?
N2 C15 H15 118.3 . . ?
C14 C15 H15 118.3 . . ?
N2 C16 C12 123.16(18) . . ?
N2 C16 C8 116.82(19) . . ?
C12 C16 C8 120.02(19) . . ?
F1 C17 F3 108.2(2) . . ?
F1 C17 F2 108.0(2) . . ?
F3 C17 F2 107.04(19) . . ?
F1 C17 C11 111.60(18) . . ?
F3 C17 C11 111.0(2) . . ?
F2 C17 C11 110.9(2) . . ?
C7 N1 C8 128.17(19) . . ?
C7 N1 H1A 120.3 . . ?
C8 N1 H1A 110.1 . . ?
C15 N2 C16 117.91(19) . . ?

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
C6 C1 C2 C3 0.0(4) . . . . ?
C1 C2 C3 C4 -0.2(4) . . . . ?
C1 C2 C3 Cl1 179.79(19) . . . . ?
C2 C3 C4 C5 -0.1(4) . . . . ?
Cl1 C3 C4 C5 179.88(19) . . . . ?
C3 C4 C5 C6 0.7(4) . . . . ?
C2 C1 C6 C5 0.5(4) . . . . ?
C2 C1 C6 C7 -179.1(2) . . . . ?
C4 C5 C6 C1 -0.8(4) . . . . ?
C4 C5 C6 C7 178.8(2) . . . . ?
C1 C6 C7 O1 -176.7(2) . . . . ?
C5 C6 C7 O1 3.7(4) . . . . ?
C1 C6 C7 N1 3.9(4) . . . . ?
C5 C6 C7 N1 -175.7(2) . . . . ?
N1 C8 C9 C10 -176.9(2) . . . . ?
C16 C8 C9 C10 0.8(4) . . . . ?
C8 C9 C10 C11 -0.2(4) . . . . ?
C9 C10 C11 C12 -0.7(4) . . . . ?
C9 C10 C11 C17 178.0(2) . . . . ?
C10 C11 C12 C13 -179.6(2) . . . . ?
C17 C11 C12 C13 1.7(4) . . . . ?
C10 C11 C12 C16 1.1(4) . . . . ?
C17 C11 C12 C16 -177.6(2) . . . . ?
C16 C12 C13 C14 0.4(4) . . . . ?
C11 C12 C13 C14 -178.9(2) . . . . ?
C12 C13 C14 C15 -0.4(4) . . . . ?
C13 C14 C15 N2 -0.2(4) . . . . ?
C13 C12 C16 N2 0.1(4) . . . . ?
C11 C12 C16 N2 179.4(2) . . . . ?
C13 C12 C16 C8 -179.9(2) . . . . ?
C11 C12 C16 C8 -0.5(3) . . . . ?
C9 C8 C16 N2 179.6(2) . . . . ?
N1 C8 C16 N2 -2.4(3) . . . . ?
C9 C8 C16 C12 -0.4(4) . . . . ?
N1 C8 C16 C12 177.6(2) . . . . ?
C10 C11 C17 F1 -2.4(3) . . . . ?
C12 C11 C17 F1 176.3(2) . . . . ?
C10 C11 C17 F3 118.4(2) . . . . ?
C12 C11 C17 F3 -62.9(3) . . . . ?
C10 C11 C17 F2 -122.8(2) . . . . ?
C12 C11 C17 F2 55.9(3) . . . . ?
O1 C7 N1 C8 -1.4(4) . . . . ?
C6 C7 N1 C8 178.0(2) . . . . ?
C9 C8 N1 C7 -6.9(4) . . . . ?
C16 C8 N1 C7 175.3(2) . . . . ?
C14 C15 N2 C16 0.7(4) . . . . ?
C12 C16 N2 C15 -0.6(4) . . . . ?
C8 C16 N2 C15 179.4(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        27.95
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max         0.532
_refine_diff_density_min         -0.537
_refine_diff_density_rms         0.080
