# Electronic Supplementary Material (ESI) for ChemComm.
# 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_RT931_0m
_database_code_depnum_ccdc_archive 'CCDC 1534787'
_audit_update_record             
;
2017-02-27 deposited with the CCDC.
2017-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H14 F3 N O2'
_chemical_formula_weight         297.27

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      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                   29.251(3)
_cell_length_b                   7.0232(7)
_cell_length_c                   16.6500(17)
_cell_angle_alpha                90
_cell_angle_beta                 122.0440(10)
_cell_angle_gamma                90
_cell_volume                     2899.4(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    90
_cell_measurement_reflns_used    5170
_cell_measurement_theta_min      2.449
_cell_measurement_theta_max      28.932

_exptl_crystal_description       prism

_exptl_crystal_colour            colorless

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_F_000             1232
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.173
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.044
_exptl_absorpt_coefficient_mu    0.116
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.914
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.333

_diffrn_reflns_number            6656
_diffrn_reflns_av_unetI/netI     0.0134
_diffrn_reflns_av_R_equivalents  0.0119
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.643
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             2545
_reflns_number_gt                2328
_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 AXS, 2006)'

_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'

_computing_data_reduction        'SAINT (Bruker AXS, 2004)'

_computing_structure_solution    'SHELXT (Sheldrick, 2014)'

_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'

_computing_molecular_graphics    'XSHELL (Bruker AXS,2002)'

_computing_publication_material  'XCIF (Bruker AXS, 2001)'


_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'


_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'


_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)+(0.0343P)²+2.8536P]
 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         2545
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0308
_refine_ls_wR_factor_ref         0.0804
_refine_ls_wR_factor_gt          0.0781
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_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
C1 C 0.19258(5) -0.10624(19) 0.34465(10) 0.0225(3) Uani 1 1 d . . . . .
C2 C 0.14929(5) 0.02486(17) 0.33511(9) 0.0182(3) Uani 1 1 d . . . . .
C3 C 0.11317(5) 0.10541(18) 0.23787(9) 0.0192(3) Uani 1 1 d . . . . .
H3A H 0.1048 0.0068 0.1894 0.023 Uiso 1 1 calc R U . . .
H3B H 0.0789 0.1495 0.2301 0.023 Uiso 1 1 calc R U . . .
C4 C 0.12209(5) 0.31788(18) 0.13632(9) 0.0181(3) Uani 1 1 d . . . . .
C5 C 0.15334(6) 0.4813(2) 0.13204(10) 0.0248(3) Uani 1 1 d . . . . .
H5A H 0.1500 0.4824 0.0703 0.037 Uiso 1 1 calc R U . . .
H5B H 0.1914 0.4681 0.1824 0.037 Uiso 1 1 calc R U . . .
H5C H 0.1391 0.6008 0.1407 0.037 Uiso 1 1 calc R U . . .
C6 C 0.14366(5) 0.05656(18) 0.40901(9) 0.0183(3) Uani 1 1 d . . . . .
C7 C 0.17656(6) -0.0392(2) 0.50452(10) 0.0266(3) Uani 1 1 d . . . . .
H7A H 0.1957 -0.1499 0.4991 0.032 Uiso 1 1 calc R U . . .
H7B H 0.1520 -0.0871 0.5240 0.032 Uiso 1 1 calc R U . . .
C8 C 0.21773(7) 0.0960(3) 0.58056(11) 0.0406(4) Uani 1 1 d . . . . .
H8A H 0.2445 0.1328 0.5650 0.061 Uiso 1 1 calc R U . . .
H8B H 0.2359 0.0319 0.6422 0.061 Uiso 1 1 calc R U . . .
H8C H 0.1992 0.2099 0.5832 0.061 Uiso 1 1 calc R U . . .
C9 C 0.10335(5) 0.19775(18) 0.40143(9) 0.0177(3) Uani 1 1 d . . . . .
C10 C 0.10345(5) 0.38451(18) 0.37235(9) 0.0193(3) Uani 1 1 d . . . . .
H10 H 0.1295 0.4216 0.3577 0.023 Uiso 1 1 calc R U . . .
C11 C 0.06609(5) 0.51572(19) 0.36466(9) 0.0214(3) Uani 1 1 d . . . . .
H11 H 0.0664 0.6423 0.3448 0.026 Uiso 1 1 calc R U . . .
C12 C 0.02800(5) 0.46121(19) 0.38623(9) 0.0207(3) Uani 1 1 d . . . . .
C13 C 0.02829(5) 0.2769(2) 0.41781(9) 0.0211(3) Uani 1 1 d . . . . .
H13 H 0.0028 0.2410 0.4338 0.025 Uiso 1 1 calc R U . . .
C14 C 0.06598(5) 0.14698(19) 0.42570(9) 0.0197(3) Uani 1 1 d . . . . .
H14 H 0.0665 0.0219 0.4478 0.024 Uiso 1 1 calc R U . . .
C15 C -0.01282(6) 0.5949(2) 0.37368(9) 0.0259(3) Uani 1 1 d . . . . .
F1 F 0.19776(3) -0.09702(12) 0.26928(6) 0.0328(2) Uani 1 1 d . . . . .
F2 F 0.24171(3) -0.06678(12) 0.42056(6) 0.0291(2) Uani 1 1 d . . . . .
F3 F 0.18311(3) -0.29097(11) 0.35275(7) 0.0328(2) Uani 1 1 d . . . . .
N1 N -0.04631(5) 0.69947(19) 0.36022(9) 0.0346(3) Uani 1 1 d . . . . .
O1 O 0.14118(4) 0.26448(13) 0.22648(6) 0.0198(2) Uani 1 1 d . . . . .
O2 O 0.08432(4) 0.24159(14) 0.06899(6) 0.0236(2) 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 1.3430(16) . ?
C1 F2 1.3461(16) . ?
C1 F3 1.3482(15) . ?
C1 C2 1.5044(18) . ?
C2 C6 1.3437(18) . ?
C2 C3 1.4975(18) . ?
C3 O1 1.4561(15) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 O2 1.2043(16) . ?
C4 O1 1.3478(15) . ?
C4 C5 1.4925(18) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C9 1.4940(17) . ?
C6 C7 1.5112(18) . ?
C7 C8 1.529(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C14 1.3979(18) . ?
C9 C10 1.3987(18) . ?
C10 C11 1.3824(18) . ?
C10 H10 0.9500 . ?
C11 C12 1.3934(19) . ?
C11 H11 0.9500 . ?
C12 C13 1.3952(19) . ?
C12 C15 1.4445(18) . ?
C13 C14 1.3826(18) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 N1 1.1471(18) . ?

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 105.90(10) . . ?
F1 C1 F3 105.71(11) . . ?
F2 C1 F3 106.13(11) . . ?
F1 C1 C2 112.19(11) . . ?
F2 C1 C2 113.11(11) . . ?
F3 C1 C2 113.17(11) . . ?
C6 C2 C3 124.64(12) . . ?
C6 C2 C1 120.66(12) . . ?
C3 C2 C1 114.64(11) . . ?
O1 C3 C2 107.92(10) . . ?
O1 C3 H3A 110.1 . . ?
C2 C3 H3A 110.1 . . ?
O1 C3 H3B 110.1 . . ?
C2 C3 H3B 110.1 . . ?
H3A C3 H3B 108.4 . . ?
O2 C4 O1 123.12(12) . . ?
O2 C4 C5 125.48(12) . . ?
O1 C4 C5 111.40(11) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C2 C6 C9 120.49(11) . . ?
C2 C6 C7 124.81(12) . . ?
C9 C6 C7 114.70(11) . . ?
C6 C7 C8 112.15(12) . . ?
C6 C7 H7A 109.2 . . ?
C8 C7 H7A 109.2 . . ?
C6 C7 H7B 109.2 . . ?
C8 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C14 C9 C10 119.00(12) . . ?
C14 C9 C6 120.63(11) . . ?
C10 C9 C6 120.34(11) . . ?
C11 C10 C9 120.70(12) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 119.59(12) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C11 C12 C13 120.41(12) . . ?
C11 C12 C15 119.79(13) . . ?
C13 C12 C15 119.79(12) . . ?
C14 C13 C12 119.56(12) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C9 120.69(12) . . ?
C13 C14 H14 119.7 . . ?
C9 C14 H14 119.7 . . ?
N1 C15 C12 177.47(15) . . ?
C4 O1 C3 115.43(10) . . ?

_refine_diff_density_max         0.275
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.037

_shelxl_version_number           2013-2



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ether/penthane'
