# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_151020a_0m
_audit_block_doi                 10.5517/ccdc.csd.cc1p6849
_database_code_depnum_ccdc_archive 'CCDC 1555150'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7OB00955K 2017
_audit_update_record             
;
2017-06-09 deposited with the CCDC.
2017-11-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H18 F3 N O2'
_chemical_formula_weight         349.34

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   13.436(7)
_cell_length_b                   8.854(5)
_cell_length_c                   14.752(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.990(6)
_cell_angle_gamma                90.00
_cell_volume                     1678.3(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2035
_cell_measurement_theta_min      2.79
_cell_measurement_theta_max      21.87

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9726
_exptl_absorpt_correction_T_max  0.9933
_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            8130
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_sigmaI/netI    0.0268
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.72
_diffrn_reflns_theta_max         25.05
_reflns_number_total             2972
_reflns_number_gt                2070
_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-97 (Sheldrick, 2008)'
_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)+(0.0571P)²+0.2054P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0042(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2972
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.1190
_refine_ls_wR_factor_gt          0.1043
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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 0.93138(13) 0.4076(2) 0.37189(11) 0.0449(4) Uani 1 1 d . . .
C2 C 0.95481(16) 0.5585(2) 0.37548(13) 0.0568(5) Uani 1 1 d . . .
H2 H 1.0191 0.5920 0.3718 0.068 Uiso 1 1 calc R . .
C3 C 0.88006(18) 0.6591(2) 0.38476(14) 0.0663(6) Uani 1 1 d . . .
H3 H 0.8930 0.7624 0.3868 0.080 Uiso 1 1 calc R . .
C4 C 0.78726(17) 0.6063(2) 0.39086(15) 0.0660(6) Uani 1 1 d . . .
C5 C 0.76232(16) 0.4555(2) 0.38748(14) 0.0601(5) Uani 1 1 d . . .
H5 H 0.6982 0.4230 0.3922 0.072 Uiso 1 1 calc R . .
C6 C 0.83575(14) 0.3544(2) 0.37684(12) 0.0462(4) Uani 1 1 d . . .
C7 C 0.83497(14) 0.1847(2) 0.37193(13) 0.0491(5) Uani 1 1 d . . .
C8 C 0.94331(14) 0.1520(2) 0.36088(12) 0.0494(5) Uani 1 1 d . . .
C9 C 1.09797(15) 0.2990(3) 0.35318(16) 0.0665(6) Uani 1 1 d . . .
H9A H 1.1258 0.2003 0.3490 0.100 Uiso 1 1 calc R . .
H9B H 1.1423 0.3514 0.4069 0.100 Uiso 1 1 calc R . .
H9C H 1.0942 0.3546 0.2964 0.100 Uiso 1 1 calc R . .
C10 C 0.82831(17) 0.1141(2) 0.46501(14) 0.0680(6) Uani 1 1 d . . .
H10A H 0.8850 0.1501 0.5166 0.102 Uiso 1 1 calc R . .
H10B H 0.8323 0.0061 0.4611 0.102 Uiso 1 1 calc R . .
H10C H 0.7635 0.1418 0.4755 0.102 Uiso 1 1 calc R . .
C11 C 0.75089(14) 0.1127(2) 0.28947(13) 0.0544(5) Uani 1 1 d . . .
H11A H 0.7683 0.0069 0.2861 0.065 Uiso 1 1 calc R . .
H11B H 0.6854 0.1167 0.3046 0.065 Uiso 1 1 calc R . .
C12 C 0.73409(14) 0.1809(2) 0.19238(14) 0.0543(5) Uani 1 1 d . . .
C13 C 0.66785(13) 0.3186(2) 0.16799(12) 0.0489(5) Uani 1 1 d . . .
C14 C 0.70715(14) 0.4552(2) 0.15041(13) 0.0548(5) Uani 1 1 d . . .
H14 H 0.7770 0.4625 0.1530 0.066 Uiso 1 1 calc R . .
C15 C 0.64454(14) 0.5820(2) 0.12888(14) 0.0577(5) Uani 1 1 d . . .
H15 H 0.6724 0.6739 0.1178 0.069 Uiso 1 1 calc R . .
C16 C 0.54061(14) 0.5718(2) 0.12387(13) 0.0556(5) Uani 1 1 d . . .
C17 C 0.50025(15) 0.4349(2) 0.14095(16) 0.0647(6) Uani 1 1 d . . .
H17 H 0.4302 0.4272 0.1374 0.078 Uiso 1 1 calc R . .
C18 C 0.56309(15) 0.3104(2) 0.16307(15) 0.0609(5) Uani 1 1 d . . .
H18 H 0.5353 0.2190 0.1750 0.073 Uiso 1 1 calc R . .
C19 C 0.5113(2) 0.8322(3) 0.0855(2) 0.0947(8) Uani 1 1 d . . .
H19A H 0.5574 0.8700 0.1436 0.142 Uiso 1 1 calc R . .
H19B H 0.4546 0.9016 0.0622 0.142 Uiso 1 1 calc R . .
H19C H 0.5486 0.8214 0.0394 0.142 Uiso 1 1 calc R . .
F1 F 0.71364(12) 0.70706(16) 0.39998(12) 0.1060(5) Uani 1 1 d . . .
F2 F 0.82895(8) 0.20615(14) 0.17742(8) 0.0646(4) Uani 1 1 d . . .
F3 F 0.68938(10) 0.06914(14) 0.12689(9) 0.0789(4) Uani 1 1 d . . .
N1 N 0.99447(11) 0.28492(17) 0.36417(11) 0.0499(4) Uani 1 1 d . . .
O1 O 0.97799(11) 0.02746(16) 0.35194(10) 0.0671(4) Uani 1 1 d . . .
O2 O 0.47166(11) 0.68953(17) 0.10204(12) 0.0769(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 1.370(3) . ?
C1 C6 1.390(2) . ?
C1 N1 1.403(2) . ?
C2 C3 1.379(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.359(3) . ?
C3 H3 0.9300 . ?
C4 F1 1.368(2) . ?
C4 C5 1.374(3) . ?
C5 C6 1.375(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.504(3) . ?
C7 C10 1.535(3) . ?
C7 C11 1.536(3) . ?
C7 C8 1.539(3) . ?
C8 O1 1.219(2) . ?
C8 N1 1.356(2) . ?
C9 N1 1.452(2) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.510(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 F2 1.374(2) . ?
C12 F3 1.391(2) . ?
C12 C13 1.490(3) . ?
C13 C14 1.375(3) . ?
C13 C18 1.390(3) . ?
C14 C15 1.383(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.380(3) . ?
C15 H15 0.9300 . ?
C16 O2 1.369(2) . ?
C16 C17 1.381(3) . ?
C17 C18 1.368(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 O2 1.419(3) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

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 122.27(17) . . ?
C2 C1 N1 128.37(17) . . ?
C6 C1 N1 109.36(16) . . ?
C1 C2 C3 117.89(19) . . ?
C1 C2 H2 121.1 . . ?
C3 C2 H2 121.1 . . ?
C4 C3 C2 119.6(2) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 F1 119.1(2) . . ?
C3 C4 C5 123.42(19) . . ?
F1 C4 C5 117.5(2) . . ?
C4 C5 C6 117.47(19) . . ?
C4 C5 H5 121.3 . . ?
C6 C5 H5 121.3 . . ?
C5 C6 C1 119.38(18) . . ?
C5 C6 C7 131.36(17) . . ?
C1 C6 C7 109.23(15) . . ?
C6 C7 C10 111.43(16) . . ?
C6 C7 C11 116.50(15) . . ?
C10 C7 C11 108.51(16) . . ?
C6 C7 C8 101.52(15) . . ?
C10 C7 C8 108.80(15) . . ?
C11 C7 C8 109.72(15) . . ?
O1 C8 N1 125.65(18) . . ?
O1 C8 C7 125.80(18) . . ?
N1 C8 C7 108.55(15) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C7 117.16(16) . . ?
C12 C11 H11A 108.0 . . ?
C7 C11 H11A 108.0 . . ?
C12 C11 H11B 108.0 . . ?
C7 C11 H11B 108.0 . . ?
H11A C11 H11B 107.3 . . ?
F2 C12 F3 103.69(15) . . ?
F2 C12 C13 110.18(16) . . ?
F3 C12 C13 107.94(16) . . ?
F2 C12 C11 109.20(15) . . ?
F3 C12 C11 106.77(16) . . ?
C13 C12 C11 118.03(16) . . ?
C14 C13 C18 118.34(18) . . ?
C14 C13 C12 122.02(17) . . ?
C18 C13 C12 119.64(17) . . ?
C13 C14 C15 121.09(17) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C16 C15 C14 119.83(18) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
O2 C16 C15 124.59(18) . . ?
O2 C16 C17 115.89(17) . . ?
C15 C16 C17 119.52(19) . . ?
C18 C17 C16 120.17(18) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C13 121.04(19) . . ?
C17 C18 H18 119.5 . . ?
C13 C18 H18 119.5 . . ?
O2 C19 H19A 109.5 . . ?
O2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C8 N1 C1 111.26(15) . . ?
C8 N1 C9 124.23(16) . . ?
C1 N1 C9 124.32(16) . . ?
C16 O2 C19 117.13(16) . . ?

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 0.3(3) . . . . ?
N1 C1 C2 C3 -178.96(17) . . . . ?
C1 C2 C3 C4 0.6(3) . . . . ?
C2 C3 C4 F1 -179.96(18) . . . . ?
C2 C3 C4 C5 -0.6(3) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
F1 C4 C5 C6 179.02(17) . . . . ?
C4 C5 C6 C1 1.2(3) . . . . ?
C4 C5 C6 C7 179.01(18) . . . . ?
C2 C1 C6 C5 -1.2(3) . . . . ?
N1 C1 C6 C5 178.14(16) . . . . ?
C2 C1 C6 C7 -179.48(16) . . . . ?
N1 C1 C6 C7 -0.09(19) . . . . ?
C5 C6 C7 C10 -63.7(3) . . . . ?
C1 C6 C7 C10 114.25(17) . . . . ?
C5 C6 C7 C11 61.5(3) . . . . ?
C1 C6 C7 C11 -120.53(17) . . . . ?
C5 C6 C7 C8 -179.37(19) . . . . ?
C1 C6 C7 C8 -1.43(18) . . . . ?
C6 C7 C8 O1 -178.38(17) . . . . ?
C10 C7 C8 O1 64.0(2) . . . . ?
C11 C7 C8 O1 -54.5(2) . . . . ?
C6 C7 C8 N1 2.52(18) . . . . ?
C10 C7 C8 N1 -115.07(17) . . . . ?
C11 C7 C8 N1 126.36(16) . . . . ?
C6 C7 C11 C12 45.2(2) . . . . ?
C10 C7 C11 C12 171.89(17) . . . . ?
C8 C7 C11 C12 -69.4(2) . . . . ?
C7 C11 C12 F2 45.2(2) . . . . ?
C7 C11 C12 F3 156.67(15) . . . . ?
C7 C11 C12 C13 -81.7(2) . . . . ?
F2 C12 C13 C14 -10.8(2) . . . . ?
F3 C12 C13 C14 -123.36(19) . . . . ?
C11 C12 C13 C14 115.6(2) . . . . ?
F2 C12 C13 C18 169.56(16) . . . . ?
F3 C12 C13 C18 57.0(2) . . . . ?
C11 C12 C13 C18 -64.1(2) . . . . ?
C18 C13 C14 C15 0.4(3) . . . . ?
C12 C13 C14 C15 -179.29(18) . . . . ?
C13 C14 C15 C16 -0.7(3) . . . . ?
C14 C15 C16 O2 -179.16(18) . . . . ?
C14 C15 C16 C17 0.3(3) . . . . ?
O2 C16 C17 C18 179.82(19) . . . . ?
C15 C16 C17 C18 0.3(3) . . . . ?
C16 C17 C18 C13 -0.6(3) . . . . ?
C14 C13 C18 C17 0.2(3) . . . . ?
C12 C13 C18 C17 179.92(19) . . . . ?
O1 C8 N1 C1 178.11(17) . . . . ?
C7 C8 N1 C1 -2.78(19) . . . . ?
O1 C8 N1 C9 2.9(3) . . . . ?
C7 C8 N1 C9 -178.03(16) . . . . ?
C2 C1 N1 C8 -178.80(17) . . . . ?
C6 C1 N1 C8 1.9(2) . . . . ?
C2 C1 N1 C9 -3.6(3) . . . . ?
C6 C1 N1 C9 177.10(16) . . . . ?
C15 C16 O2 C19 -1.4(3) . . . . ?
C17 C16 O2 C19 179.1(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.036
