# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_1e
_database_code_depnum_ccdc_archive 'CCDC 1412036'
_audit_update_record             
;
2015-07-10 deposited with the CCDC.
2015-11-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H20 N O, C2 F3 O2'
_chemical_formula_sum            'C14 H20 F3 N O3'
_chemical_formula_weight         307.31

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   7.7764(12)
_cell_length_b                   15.755(2)
_cell_length_c                   25.521(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3126.7(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    1654
_cell_measurement_theta_min      3
_cell_measurement_theta_max      30

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_F_000             1296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.114
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX2 CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31077
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_av_R_equivalents  0.0858
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.586
_diffrn_reflns_theta_max         26.993
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3402
_reflns_number_gt                2467
_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, 2005)'
_computing_cell_refinement       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'APEX2 (Bruker, 2005)'
_computing_structure_solution    'APEX2 (Bruker, 2005)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/6 (Sheldrick, 2014)'
_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)+(0.0500P)²+2.5000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0062(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3402
_refine_ls_number_parameters     216
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1015
_refine_ls_R_factor_gt           0.0734
_refine_ls_wR_factor_ref         0.1850
_refine_ls_wR_factor_gt          0.1742
_refine_ls_goodness_of_fit_ref   1.376
_refine_ls_restrained_S_all      1.376
_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
O1 O 0.2772(3) 0.17587(13) 0.41339(7) 0.0327(5) Uani 1 1 d . . . . .
H1O H 0.3616 0.1359 0.3977 0.039 Uiso 1 1 d R U . . .
N1 N 0.1804(3) 0.12641(15) 0.62814(9) 0.0270(6) Uani 1 1 d . . . . .
H1N H 0.2783 0.0912 0.6435 0.032 Uiso 1 1 d R U . . .
C1 C 0.2096(3) 0.14177(17) 0.57204(11) 0.0252(6) Uani 1 1 d . . . . .
C2 C 0.3280(4) 0.09171(18) 0.54599(11) 0.0279(6) Uani 1 1 d . . . . .
H2A H 0.3922 0.0502 0.5646 0.034 Uiso 1 1 calc R U . . .
C3 C 0.3527(4) 0.10222(18) 0.49281(11) 0.0299(7) Uani 1 1 d . . . . .
H3A H 0.4343 0.0680 0.4749 0.036 Uiso 1 1 calc R U . . .
C4 C 0.2591(4) 0.16239(17) 0.46542(11) 0.0273(6) Uani 1 1 d . . . . .
C5 C 0.1442(4) 0.21370(19) 0.49206(11) 0.0319(7) Uani 1 1 d . . . . .
H5A H 0.0823 0.2563 0.4736 0.038 Uiso 1 1 calc R U . . .
C6 C 0.1190(4) 0.20348(18) 0.54523(12) 0.0300(7) Uani 1 1 d . . . . .
H6A H 0.0396 0.2387 0.5633 0.036 Uiso 1 1 calc R U . . .
C7 C 0.0186(4) 0.0729(2) 0.63838(13) 0.0364(8) Uani 1 1 d . . . . .
H7A H 0.0183 0.0579 0.6765 0.044 Uiso 1 1 calc R U . . .
C8 C 0.0322(5) -0.0091(2) 0.60813(15) 0.0489(9) Uani 1 1 d . . . . .
H8A H -0.0569 -0.0486 0.6202 0.073 Uiso 1 1 calc R U . . .
H8B H 0.1458 -0.0343 0.6139 0.073 Uiso 1 1 calc R U . . .
H8C H 0.0163 0.0023 0.5707 0.073 Uiso 1 1 calc R U . . .
C9 C -0.1462(4) 0.1209(3) 0.62734(17) 0.0546(10) Uani 1 1 d . . . . .
H9A H -0.2450 0.0860 0.6375 0.082 Uiso 1 1 calc R U . . .
H9B H -0.1531 0.1340 0.5899 0.082 Uiso 1 1 calc R U . . .
H9C H -0.1471 0.1738 0.6475 0.082 Uiso 1 1 calc R U . . .
C10 C 0.1934(4) 0.20718(19) 0.66149(12) 0.0339(7) Uani 1 1 d . . . . .
H10A H 0.1024 0.2480 0.6500 0.041 Uiso 1 1 calc R U . . .
C11 C 0.1655(5) 0.1859(2) 0.71907(12) 0.0457(9) Uani 1 1 d . . . . .
H11A H 0.1869 0.2365 0.7404 0.069 Uiso 1 1 calc R U . . .
H11B H 0.2450 0.1407 0.7295 0.069 Uiso 1 1 calc R U . . .
H11C H 0.0469 0.1668 0.7243 0.069 Uiso 1 1 calc R U . . .
C12 C 0.3679(5) 0.2472(2) 0.65283(13) 0.0409(8) Uani 1 1 d . . . . .
H12A H 0.3833 0.2594 0.6155 0.061 Uiso 1 1 calc R U . . .
H12B H 0.4579 0.2080 0.6646 0.061 Uiso 1 1 calc R U . . .
H12C H 0.3756 0.3001 0.6729 0.061 Uiso 1 1 calc R U . . .
O2 O 0.4275(3) 0.03572(13) 0.67964(8) 0.0362(5) Uani 1 1 d . . . . .
O3 O 0.4894(3) -0.07016(15) 0.62462(8) 0.0424(6) Uani 1 1 d . . . . .
C13 C 0.4939(4) -0.03224(18) 0.66663(11) 0.0275(6) Uani 1 1 d . . . . .
C14 C 0.5995(4) -0.07609(19) 0.70988(11) 0.0324(7) Uani 1 1 d . . . . .
F1 F 0.4890(7) -0.1403(3) 0.73133(18) 0.0446(11) Uani 0.431(3) 1 d . . P A 1
F2 F 0.7325(7) -0.1237(4) 0.6928(2) 0.0428(14) Uani 0.431(3) 1 d . . P A 1
F3 F 0.6421(8) -0.0321(3) 0.7495(3) 0.0467(10) Uani 0.431(3) 1 d . . P A 1
F1' F 0.5682(12) -0.0512(6) 0.7573(3) 0.0446(11) Uani 0.354(4) 1 d . . P A 2
F2' F 0.6599(12) -0.1513(5) 0.6984(3) 0.0428(14) Uani 0.354(4) 1 d . . P A 2
F3' F 0.7520(8) -0.0233(4) 0.7162(3) 0.0467(10) Uani 0.354(4) 1 d . . P A 2
F1" F 0.5203(15) -0.0853(8) 0.7549(4) 0.0446(11) Uani 0.214(3) 1 d . . P A 3
F3" F 0.7673(14) -0.0614(8) 0.6980(4) 0.0467(10) Uani 0.214(3) 1 d . . P A 3
F2" F 0.5735(18) -0.1528(7) 0.7112(4) 0.0428(14) Uani 0.214(3) 1 d . . P A 3


_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
O1 C4 1.352(3) . ?
O1 H1O 0.9935 . ?
N1 C1 1.470(3) . ?
N1 C10 1.534(4) . ?
N1 C7 1.537(4) . ?
N1 H1N 1.0206 . ?
C1 C6 1.382(4) . ?
C1 C2 1.383(4) . ?
C2 C3 1.381(4) . ?
C2 H2A 0.9500 . ?
C3 C4 1.384(4) . ?
C3 H3A 0.9500 . ?
C4 C5 1.384(4) . ?
C5 C6 1.381(4) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 C8 1.508(5) . ?
C7 C9 1.515(5) . ?
C7 H7A 1.0000 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C12 1.513(4) . ?
C10 C11 1.523(4) . ?
C10 H10A 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
O2 C13 1.234(3) . ?
O3 C13 1.228(3) . ?
C13 C14 1.540(4) . ?
C14 F2" 1.225(12) . ?
C14 F3 1.270(6) . ?
C14 F1' 1.296(8) . ?
C14 F2' 1.308(9) . ?
C14 F1" 1.311(11) . ?
C14 F2 1.350(6) . ?
C14 F3" 1.359(11) . ?
C14 F1 1.436(5) . ?
C14 F3' 1.457(7) . ?
F1" F2" 1.595(16) . ?

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
C4 O1 H1O 111.3 . . ?
C1 N1 C10 113.2(2) . . ?
C1 N1 C7 112.5(2) . . ?
C10 N1 C7 114.5(2) . . ?
C1 N1 H1N 110.4 . . ?
C10 N1 H1N 100.9 . . ?
C7 N1 H1N 104.3 . . ?
C6 C1 C2 120.2(3) . . ?
C6 C1 N1 121.3(3) . . ?
C2 C1 N1 118.5(2) . . ?
C3 C2 C1 119.8(3) . . ?
C3 C2 H2A 120.1 . . ?
C1 C2 H2A 120.1 . . ?
C2 C3 C4 120.4(3) . . ?
C2 C3 H3A 119.8 . . ?
C4 C3 H3A 119.8 . . ?
O1 C4 C5 117.3(3) . . ?
O1 C4 C3 123.3(3) . . ?
C5 C4 C3 119.4(3) . . ?
C6 C5 C4 120.4(3) . . ?
C6 C5 H5A 119.8 . . ?
C4 C5 H5A 119.8 . . ?
C5 C6 C1 119.7(3) . . ?
C5 C6 H6A 120.1 . . ?
C1 C6 H6A 120.1 . . ?
C8 C7 C9 113.0(3) . . ?
C8 C7 N1 109.0(3) . . ?
C9 C7 N1 112.7(2) . . ?
C8 C7 H7A 107.2 . . ?
C9 C7 H7A 107.2 . . ?
N1 C7 H7A 107.2 . . ?
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 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C12 C10 C11 111.1(3) . . ?
C12 C10 N1 108.9(2) . . ?
C11 C10 N1 110.1(2) . . ?
C12 C10 H10A 108.9 . . ?
C11 C10 H10A 108.9 . . ?
N1 C10 H10A 108.9 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O3 C13 O2 130.2(3) . . ?
O3 C13 C14 115.0(3) . . ?
O2 C13 C14 114.8(2) . . ?
F1' C14 F2' 123.5(5) . . ?
F2" C14 F1" 77.8(8) . . ?
F3 C14 F2 111.1(4) . . ?
F2" C14 F3" 109.4(8) . . ?
F1" C14 F3" 131.7(7) . . ?
F3 C14 F1 103.7(4) . . ?
F2 C14 F1 100.9(4) . . ?
F1' C14 F3' 82.9(6) . . ?
F2' C14 F3' 104.4(5) . . ?
F2" C14 C13 112.0(5) . . ?
F3 C14 C13 117.7(3) . . ?
F1' C14 C13 115.7(4) . . ?
F2' C14 C13 115.9(4) . . ?
F1" C14 C13 115.3(5) . . ?
F2 C14 C13 115.3(3) . . ?
F3" C14 C13 106.0(5) . . ?
F1 C14 C13 105.7(3) . . ?
F3' C14 C13 104.9(3) . . ?
C14 F1" F2" 48.7(6) . . ?
C14 F2" F1" 53.5(6) . . ?

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
C10 N1 C1 C6 -52.4(3) . . . . ?
C7 N1 C1 C6 79.4(3) . . . . ?
C10 N1 C1 C2 129.0(3) . . . . ?
C7 N1 C1 C2 -99.3(3) . . . . ?
C6 C1 C2 C3 -1.5(4) . . . . ?
N1 C1 C2 C3 177.2(3) . . . . ?
C1 C2 C3 C4 -0.2(4) . . . . ?
C2 C3 C4 O1 180.0(3) . . . . ?
C2 C3 C4 C5 1.9(4) . . . . ?
O1 C4 C5 C6 179.9(3) . . . . ?
C3 C4 C5 C6 -1.9(4) . . . . ?
C4 C5 C6 C1 0.3(4) . . . . ?
C2 C1 C6 C5 1.5(4) . . . . ?
N1 C1 C6 C5 -177.2(3) . . . . ?
C1 N1 C7 C8 55.6(3) . . . . ?
C10 N1 C7 C8 -173.3(3) . . . . ?
C1 N1 C7 C9 -70.8(3) . . . . ?
C10 N1 C7 C9 60.3(4) . . . . ?
C1 N1 C10 C12 -56.7(3) . . . . ?
C7 N1 C10 C12 172.5(2) . . . . ?
C1 N1 C10 C11 -178.8(3) . . . . ?
C7 N1 C10 C11 50.5(3) . . . . ?
O3 C13 C14 F2" -42.6(8) . . . . ?
O2 C13 C14 F2" 137.6(8) . . . . ?
O3 C13 C14 F3 164.1(5) . . . . ?
O2 C13 C14 F3 -15.6(6) . . . . ?
O3 C13 C14 F1' -161.5(6) . . . . ?
O2 C13 C14 F1' 18.7(6) . . . . ?
O3 C13 C14 F2' -5.4(6) . . . . ?
O2 C13 C14 F2' 174.9(5) . . . . ?
O3 C13 C14 F1" -129.1(7) . . . . ?
O2 C13 C14 F1" 51.1(8) . . . . ?
O3 C13 C14 F2 29.8(5) . . . . ?
O2 C13 C14 F2 -149.9(4) . . . . ?
O3 C13 C14 F3" 76.6(6) . . . . ?
O2 C13 C14 F3" -103.1(6) . . . . ?
O3 C13 C14 F1 -80.7(4) . . . . ?
O2 C13 C14 F1 99.6(4) . . . . ?
O3 C13 C14 F3' 109.2(4) . . . . ?
O2 C13 C14 F3' -70.5(4) . . . . ?
F3" C14 F1" F2" -105.3(10) . . . . ?
C13 C14 F1" F2" 108.7(7) . . . . ?
F3" C14 F2" F1" 130.2(7) . . . . ?
C13 C14 F2" F1" -112.6(6) . . . . ?

_refine_diff_density_max         0.418
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.057

_shelxl_version_number           2014/6

