# 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_160808LT_0m
_database_code_depnum_ccdc_archive 'CCDC 1529475'
_audit_update_record             
;
2017-01-24 deposited with the CCDC.
2017-05-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H23 Cl F3 N O2'
_chemical_formula_weight         485.91

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   9.3330(4)
_cell_length_b                   10.1568(4)
_cell_length_c                   12.9438(5)
_cell_angle_alpha                85.635(2)
_cell_angle_beta                 69.299(2)
_cell_angle_gamma                88.318(2)
_cell_volume                     1144.44(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8758
_cell_measurement_theta_min      2.3479
_cell_measurement_theta_max      26.3767

_exptl_crystal_description       lump
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_F_000             504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.217
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8989
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            19165
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.686
_diffrn_reflns_theta_max         26.407
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4667
_reflns_number_gt                4209
_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       'Bruker APEX2'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0609P)²+1.1330P] 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         4667
_refine_ls_number_parameters     310
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.1282
_refine_ls_wR_factor_gt          0.1212
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.001
_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 0.96183(6) 1.35613(5) 0.58214(4) 0.03166(16) Uani 1 1 d . . . . .
F1 F 0.35886(15) 0.44056(12) 0.62147(11) 0.0321(3) Uani 1 1 d . . . . .
F2 F 0.18483(14) 0.56021(13) 0.73053(11) 0.0335(3) Uani 1 1 d . . . . .
F3 F 0.32348(16) 0.63969(13) 0.56788(11) 0.0361(3) Uani 1 1 d . . . . .
O1 O 0.64742(16) 0.96639(14) 1.04675(11) 0.0245(3) Uani 1 1 d . . . . .
O2 O 1.05359(15) 0.82769(14) 0.86132(11) 0.0246(3) Uani 1 1 d . . . . .
N1 N 0.72556(17) 0.80609(15) 0.92393(12) 0.0164(3) Uani 1 1 d . . . . .
C1 C 0.8765(2) 1.24051(19) 0.69234(16) 0.0227(4) Uani 1 1 d . . . . .
C2 C 0.9243(2) 1.23040(19) 0.78245(18) 0.0250(4) Uani 1 1 d . . . . .
H23 H 0.9979 1.2900 0.7872 0.030 Uiso 1 1 calc R U . . .
C3 C 0.8629(2) 1.13177(19) 0.86562(17) 0.0227(4) Uani 1 1 d . . . . .
H22 H 0.8937 1.1250 0.9284 0.027 Uiso 1 1 calc R U . . .
C4 C 0.7565(2) 1.04223(18) 0.85856(15) 0.0179(4) Uani 1 1 d . . . . .
C5 C 0.7029(2) 0.93520(18) 0.95068(15) 0.0182(4) Uani 1 1 d . . . . .
C6 C 0.7776(2) 0.77209(17) 0.81096(15) 0.0165(4) Uani 1 1 d . . . . .
C7 C 0.9205(2) 0.79521(18) 0.74032(15) 0.0182(4) Uani 1 1 d . . . . .
H15 H 0.9455 0.7720 0.6662 0.022 Uiso 1 1 calc R U . . .
C8 C 1.0424(2) 0.85500(18) 0.77071(15) 0.0176(4) Uani 1 1 d . . . . .
C9 C 1.1530(2) 0.94750(18) 0.68688(15) 0.0183(4) Uani 1 1 d . . . . .
C10 C 1.2643(2) 1.00636(19) 0.71712(16) 0.0221(4) Uani 1 1 d . . . . .
H19 H 1.2708 0.9842 0.7880 0.026 Uiso 1 1 calc R U . . .
C11 C 1.3649(2) 1.0967(2) 0.64432(18) 0.0261(4) Uani 1 1 d . . . . .
H18 H 1.4401 1.1367 0.6656 0.031 Uiso 1 1 calc R U . . .
C12 C 1.3572(2) 1.1299(2) 0.53998(18) 0.0277(4) Uani 1 1 d . . . . .
H1 H 1.4275 1.1916 0.4902 0.033 Uiso 1 1 calc R U . . .
C13 C 0.7022(2) 0.69277(19) 1.01277(15) 0.0197(4) Uani 1 1 d . . . . .
C14 C 0.7739(3) 0.5670(2) 0.95838(17) 0.0273(4) Uani 1 1 d . . . . .
H2 H 0.7202 0.5415 0.9102 0.041 Uiso 1 1 calc R U . . .
H4 H 0.7655 0.4958 1.0158 0.041 Uiso 1 1 calc R U . . .
H3 H 0.8822 0.5829 0.9143 0.041 Uiso 1 1 calc R U . . .
C15 C 0.7856(3) 0.7235(2) 1.09088(17) 0.0304(5) Uani 1 1 d . . . . .
H6 H 0.8918 0.7478 1.0474 0.046 Uiso 1 1 calc R U . . .
H5 H 0.7842 0.6453 1.1405 0.046 Uiso 1 1 calc R U . . .
H7 H 0.7341 0.7970 1.1347 0.046 Uiso 1 1 calc R U . . .
C16 C 0.5309(2) 0.6720(2) 1.07606(18) 0.0295(5) Uani 1 1 d . . . . .
H8 H 0.4852 0.7542 1.1086 0.044 Uiso 1 1 calc R U . . .
H10 H 0.5164 0.6018 1.1351 0.044 Uiso 1 1 calc R U . . .
H9 H 0.4815 0.6469 1.0251 0.044 Uiso 1 1 calc R U . . .
C17 C 0.6597(2) 0.71387(17) 0.77510(14) 0.0165(4) Uani 1 1 d . . . . .
C18 C 0.5058(2) 0.75011(18) 0.82063(15) 0.0180(4) Uani 1 1 d . . . . .
H14 H 0.4749 0.8102 0.8773 0.022 Uiso 1 1 calc R U . . .
C19 C 0.3974(2) 0.69894(18) 0.78360(15) 0.0183(4) Uani 1 1 d . . . . .
H13 H 0.2928 0.7241 0.8146 0.022 Uiso 1 1 calc R U . . .
C20 C 0.4433(2) 0.61070(18) 0.70080(15) 0.0179(4) Uani 1 1 d . . . . .
C21 C 0.3279(2) 0.5621(2) 0.65604(16) 0.0233(4) Uani 1 1 d . . . . .
C22 C 0.5951(2) 0.57172(18) 0.65644(15) 0.0205(4) Uani 1 1 d . . . . .
H12 H 0.6251 0.5100 0.6010 0.025 Uiso 1 1 calc R U . . .
C23 C 0.7026(2) 0.62309(18) 0.69322(15) 0.0191(4) Uani 1 1 d . . . . .
H11 H 0.8067 0.5965 0.6626 0.023 Uiso 1 1 calc R U . . .
C24 C 1.2470(2) 1.0727(2) 0.50892(17) 0.0272(4) Uani 1 1 d . . . . .
H16 H 1.2408 1.0953 0.4380 0.033 Uiso 1 1 calc R U . . .
C25 C 1.1452(2) 0.9815(2) 0.58277(16) 0.0223(4) Uani 1 1 d . . . . .
H17 H 1.0695 0.9422 0.5617 0.027 Uiso 1 1 calc R U . . .
C26 C 0.7057(2) 1.05858(19) 0.76910(16) 0.0207(4) Uani 1 1 d . . . . .
H20 H 0.6299 1.0010 0.7648 0.025 Uiso 1 1 calc R U . . .
C27 C 0.7650(2) 1.15810(19) 0.68627(16) 0.0227(4) Uani 1 1 d . . . . .
H21 H 0.7292 1.1695 0.6260 0.027 Uiso 1 1 calc R U . . .


_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 C1 1.745(2) . ?
F1 C21 1.333(2) . ?
F2 C21 1.342(2) . ?
F3 C21 1.349(2) . ?
O1 C5 1.229(2) . ?
O2 C8 1.224(2) . ?
N1 C5 1.373(2) . ?
N1 C6 1.435(2) . ?
N1 C13 1.527(2) . ?
C1 C27 1.382(3) . ?
C1 C2 1.384(3) . ?
C2 C3 1.387(3) . ?
C2 H23 0.9500 . ?
C3 C4 1.397(3) . ?
C3 H22 0.9500 . ?
C4 C26 1.395(3) . ?
C4 C5 1.506(3) . ?
C6 C7 1.339(3) . ?
C6 C17 1.489(2) . ?
C7 C8 1.487(2) . ?
C7 H15 0.9500 . ?
C8 C9 1.495(3) . ?
C9 C25 1.392(3) . ?
C9 C10 1.396(3) . ?
C10 C11 1.381(3) . ?
C10 H19 0.9500 . ?
C11 C12 1.393(3) . ?
C11 H18 0.9500 . ?
C12 C24 1.385(3) . ?
C12 H1 0.9500 . ?
C13 C14 1.526(3) . ?
C13 C16 1.529(3) . ?
C13 C15 1.531(3) . ?
C14 H2 0.9800 . ?
C14 H4 0.9800 . ?
C14 H3 0.9800 . ?
C15 H6 0.9800 . ?
C15 H5 0.9800 . ?
C15 H7 0.9800 . ?
C16 H8 0.9800 . ?
C16 H10 0.9800 . ?
C16 H9 0.9800 . ?
C17 C18 1.396(3) . ?
C17 C23 1.400(3) . ?
C18 C19 1.391(3) . ?
C18 H14 0.9500 . ?
C19 C20 1.391(3) . ?
C19 H13 0.9500 . ?
C20 C22 1.385(3) . ?
C20 C21 1.502(2) . ?
C22 C23 1.383(3) . ?
C22 H12 0.9500 . ?
C23 H11 0.9500 . ?
C24 C25 1.396(3) . ?
C24 H16 0.9500 . ?
C25 H17 0.9500 . ?
C26 C27 1.388(3) . ?
C26 H20 0.9500 . ?
C27 H21 0.9500 . ?

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
C5 N1 C6 121.44(15) . . ?
C5 N1 C13 121.47(14) . . ?
C6 N1 C13 117.05(14) . . ?
C27 C1 C2 121.27(18) . . ?
C27 C1 Cl1 119.00(16) . . ?
C2 C1 Cl1 119.70(15) . . ?
C1 C2 C3 118.89(18) . . ?
C1 C2 H23 120.6 . . ?
C3 C2 H23 120.6 . . ?
C2 C3 C4 121.03(18) . . ?
C2 C3 H22 119.5 . . ?
C4 C3 H22 119.5 . . ?
C26 C4 C3 118.63(17) . . ?
C26 C4 C5 124.71(16) . . ?
C3 C4 C5 116.65(16) . . ?
O1 C5 N1 122.63(17) . . ?
O1 C5 C4 119.01(16) . . ?
N1 C5 C4 118.28(15) . . ?
C7 C6 N1 122.96(16) . . ?
C7 C6 C17 121.54(16) . . ?
N1 C6 C17 115.45(15) . . ?
C6 C7 C8 124.03(16) . . ?
C6 C7 H15 118.0 . . ?
C8 C7 H15 118.0 . . ?
O2 C8 C7 120.95(17) . . ?
O2 C8 C9 120.76(16) . . ?
C7 C8 C9 118.28(16) . . ?
C25 C9 C10 119.04(18) . . ?
C25 C9 C8 122.92(16) . . ?
C10 C9 C8 117.98(17) . . ?
C11 C10 C9 120.16(18) . . ?
C11 C10 H19 119.9 . . ?
C9 C10 H19 119.9 . . ?
C10 C11 C12 120.58(18) . . ?
C10 C11 H18 119.7 . . ?
C12 C11 H18 119.7 . . ?
C24 C12 C11 119.95(19) . . ?
C24 C12 H1 120.0 . . ?
C11 C12 H1 120.0 . . ?
C14 C13 N1 109.47(15) . . ?
C14 C13 C16 110.03(16) . . ?
N1 C13 C16 109.67(15) . . ?
C14 C13 C15 106.95(17) . . ?
N1 C13 C15 109.56(15) . . ?
C16 C13 C15 111.11(17) . . ?
C13 C14 H2 109.5 . . ?
C13 C14 H4 109.5 . . ?
H2 C14 H4 109.5 . . ?
C13 C14 H3 109.5 . . ?
H2 C14 H3 109.5 . . ?
H4 C14 H3 109.5 . . ?
C13 C15 H6 109.5 . . ?
C13 C15 H5 109.5 . . ?
H6 C15 H5 109.5 . . ?
C13 C15 H7 109.5 . . ?
H6 C15 H7 109.5 . . ?
H5 C15 H7 109.5 . . ?
C13 C16 H8 109.5 . . ?
C13 C16 H10 109.5 . . ?
H8 C16 H10 109.5 . . ?
C13 C16 H9 109.5 . . ?
H8 C16 H9 109.5 . . ?
H10 C16 H9 109.5 . . ?
C18 C17 C23 118.95(16) . . ?
C18 C17 C6 120.95(16) . . ?
C23 C17 C6 120.09(16) . . ?
C19 C18 C17 120.51(16) . . ?
C19 C18 H14 119.7 . . ?
C17 C18 H14 119.7 . . ?
C20 C19 C18 119.46(17) . . ?
C20 C19 H13 120.3 . . ?
C18 C19 H13 120.3 . . ?
C22 C20 C19 120.67(16) . . ?
C22 C20 C21 119.91(17) . . ?
C19 C20 C21 119.37(17) . . ?
F1 C21 F2 107.08(15) . . ?
F1 C21 F3 106.00(15) . . ?
F2 C21 F3 106.23(16) . . ?
F1 C21 C20 112.78(16) . . ?
F2 C21 C20 112.76(16) . . ?
F3 C21 C20 111.52(15) . . ?
C23 C22 C20 119.70(17) . . ?
C23 C22 H12 120.2 . . ?
C20 C22 H12 120.2 . . ?
C22 C23 C17 120.68(17) . . ?
C22 C23 H11 119.7 . . ?
C17 C23 H11 119.7 . . ?
C12 C24 C25 119.36(19) . . ?
C12 C24 H16 120.3 . . ?
C25 C24 H16 120.3 . . ?
C9 C25 C24 120.91(18) . . ?
C9 C25 H17 119.5 . . ?
C24 C25 H17 119.5 . . ?
C27 C26 C4 120.65(17) . . ?
C27 C26 H20 119.7 . . ?
C4 C26 H20 119.7 . . ?
C1 C27 C26 119.37(18) . . ?
C1 C27 H21 120.3 . . ?
C26 C27 H21 120.3 . . ?

_refine_diff_density_max         0.649
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.068

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_160947lt_0m
_database_code_depnum_ccdc_archive 'CCDC 1529472'
_audit_update_record             
;
2017-01-24 deposited with the CCDC.
2017-05-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H25 N O2'
_chemical_formula_weight         347.44

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   9.7947(6)
_cell_length_b                   10.1593(6)
_cell_length_c                   10.2676(6)
_cell_angle_alpha                77.035(2)
_cell_angle_beta                 75.489(3)
_cell_angle_gamma                71.193(2)
_cell_volume                     924.74(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6851
_cell_measurement_theta_min      2.6272
_cell_measurement_theta_max      26.3349

_exptl_crystal_description       Tabullar
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_F_000             372
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8903
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            14156
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.074
_diffrn_reflns_theta_max         26.365
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3785
_reflns_number_gt                3314
_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       'Bruker APEX2'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0911P)²+0.4379P] 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         3785
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0482
_refine_ls_wR_factor_ref         0.1604
_refine_ls_wR_factor_gt          0.1386
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_restrained_S_all      1.120
_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 0.13278(14) 0.14002(15) 0.15013(13) 0.0319(3) Uani 1 1 d . . . . .
O2 O 0.17570(13) 0.47229(13) 0.13134(11) 0.0240(3) Uani 1 1 d . . . . .
N1 N 0.20681(14) 0.20545(14) 0.31289(13) 0.0181(3) Uani 1 1 d . . . . .
C1 C 0.2163(2) 0.75148(19) 0.09343(17) 0.0255(4) Uani 1 1 d . . . . .
H26 H 0.1823 0.7317 0.0187 0.031 Uiso 1 1 calc R U . . .
H25 H 0.1903 0.8525 0.1008 0.031 Uiso 1 1 calc R U . . .
C2 C 0.21654(18) 0.64767(17) 0.22344(16) 0.0208(4) Uani 1 1 d . . . . .
H17 H 0.1932 0.6872 0.3099 0.025 Uiso 1 1 calc R U . . .
C3 C 0.17734(17) 0.51564(17) 0.23278(16) 0.0194(3) Uani 1 1 d . . . . .
C4 C 0.15022(17) 0.43882(17) 0.37332(16) 0.0186(3) Uani 1 1 d . . . . .
H18 H 0.1138 0.4942 0.4445 0.022 Uiso 1 1 calc R U . . .
C5 C 0.17173(16) 0.29876(17) 0.41086(16) 0.0176(3) Uani 1 1 d . . . . .
C6 C 0.10455(17) 0.20891(18) 0.24185(15) 0.0195(3) Uani 1 1 d . . . . .
C7 C -0.05296(17) 0.29548(17) 0.27992(16) 0.0183(3) Uani 1 1 d . . . . .
C8 C -0.13953(18) 0.27414(17) 0.40874(16) 0.0192(3) Uani 1 1 d . . . . .
H3 H -0.0959 0.2135 0.4814 0.023 Uiso 1 1 calc R U . . .
C9 C -0.28926(18) 0.34122(18) 0.43110(17) 0.0215(4) Uani 1 1 d . . . . .
H24 H -0.3478 0.3254 0.5189 0.026 Uiso 1 1 calc R U . . .
C10 C -0.35432(18) 0.43153(18) 0.32601(17) 0.0232(4) Uani 1 1 d . . . . .
H2 H -0.4567 0.4779 0.3418 0.028 Uiso 1 1 calc R U . . .
C11 C -0.11877(18) 0.38508(18) 0.17437(16) 0.0214(4) Uani 1 1 d . . . . .
H5 H -0.0609 0.3994 0.0860 0.026 Uiso 1 1 calc R U . . .
C12 C -0.26788(19) 0.45321(19) 0.19768(17) 0.0235(4) Uani 1 1 d . . . . .
H4 H -0.3114 0.5152 0.1255 0.028 Uiso 1 1 calc R U . . .
C13 C 0.36585(17) 0.11957(19) 0.27203(17) 0.0225(4) Uani 1 1 d . . . . .
C14 C 0.4614(2) 0.1483(3) 0.3530(3) 0.0445(6) Uani 1 1 d . . . . .
H7 H 0.4553 0.2487 0.3337 0.067 Uiso 1 1 calc R U . . .
H6 H 0.5636 0.0931 0.3267 0.067 Uiso 1 1 calc R U . . .
H8 H 0.4266 0.1213 0.4505 0.067 Uiso 1 1 calc R U . . .
C15 C 0.3760(2) -0.0365(2) 0.3020(2) 0.0342(4) Uani 1 1 d . . . . .
H9 H 0.3473 -0.0648 0.4004 0.051 Uiso 1 1 calc R U . . .
H11 H 0.4773 -0.0910 0.2704 0.051 Uiso 1 1 calc R U . . .
H10 H 0.3100 -0.0544 0.2547 0.051 Uiso 1 1 calc R U . . .
C16 C 0.4235(2) 0.1634(3) 0.1207(2) 0.0418(5) Uani 1 1 d . . . . .
H14 H 0.3687 0.1395 0.0659 0.063 Uiso 1 1 calc R U . . .
H12 H 0.5281 0.1137 0.0974 0.063 Uiso 1 1 calc R U . . .
H13 H 0.4105 0.2652 0.1020 0.063 Uiso 1 1 calc R U . . .
C17 C 0.3589(2) 0.6601(2) 0.12607(19) 0.0289(4) Uani 1 1 d . . . . .
H16 H 0.4213 0.7041 0.1542 0.035 Uiso 1 1 calc R U . . .
H15 H 0.4134 0.5832 0.0721 0.035 Uiso 1 1 calc R U . . .
C18 C 0.16456(17) 0.23207(17) 0.55593(16) 0.0184(3) Uani 1 1 d . . . . .
C19 C 0.18416(18) 0.29913(18) 0.65330(17) 0.0219(4) Uani 1 1 d . . . . .
H23 H 0.2035 0.3881 0.6259 0.026 Uiso 1 1 calc R U . . .
C20 C 0.17541(19) 0.23642(19) 0.78884(17) 0.0249(4) Uani 1 1 d . . . . .
H22 H 0.1881 0.2833 0.8534 0.030 Uiso 1 1 calc R U . . .
C21 C 0.14847(19) 0.10690(19) 0.83078(17) 0.0242(4) Uani 1 1 d . . . . .
H21 H 0.1425 0.0648 0.9237 0.029 Uiso 1 1 calc R U . . .
C22 C 0.13012(18) 0.03827(18) 0.73644(17) 0.0218(4) Uani 1 1 d . . . . .
H20 H 0.1116 -0.0511 0.7649 0.026 Uiso 1 1 calc R U . . .
C23 C 0.13884(17) 0.10020(17) 0.60012(16) 0.0185(3) Uani 1 1 d . . . . .
H19 H 0.1271 0.0520 0.5362 0.022 Uiso 1 1 calc R U . . .


_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 C6 1.222(2) . ?
O2 C3 1.224(2) . ?
N1 C6 1.367(2) . ?
N1 C5 1.440(2) . ?
N1 C13 1.525(2) . ?
C1 C17 1.477(3) . ?
C1 C2 1.504(2) . ?
C1 H26 0.9900 . ?
C1 H25 0.9900 . ?
C2 C3 1.487(2) . ?
C2 C17 1.522(2) . ?
C2 H17 1.0000 . ?
C3 C4 1.483(2) . ?
C4 C5 1.349(2) . ?
C4 H18 0.9500 . ?
C5 C18 1.486(2) . ?
C6 C7 1.511(2) . ?
C7 C8 1.394(2) . ?
C7 C11 1.396(2) . ?
C8 C9 1.387(2) . ?
C8 H3 0.9500 . ?
C9 C10 1.391(2) . ?
C9 H24 0.9500 . ?
C10 C12 1.390(2) . ?
C10 H2 0.9500 . ?
C11 C12 1.385(2) . ?
C11 H5 0.9500 . ?
C12 H4 0.9500 . ?
C13 C15 1.521(3) . ?
C13 C14 1.525(3) . ?
C13 C16 1.531(2) . ?
C14 H7 0.9800 . ?
C14 H6 0.9800 . ?
C14 H8 0.9800 . ?
C15 H9 0.9800 . ?
C15 H11 0.9800 . ?
C15 H10 0.9800 . ?
C16 H14 0.9800 . ?
C16 H12 0.9800 . ?
C16 H13 0.9800 . ?
C17 H16 0.9900 . ?
C17 H15 0.9900 . ?
C18 C23 1.397(2) . ?
C18 C19 1.410(2) . ?
C19 C20 1.388(2) . ?
C19 H23 0.9500 . ?
C20 C21 1.378(3) . ?
C20 H22 0.9500 . ?
C21 C22 1.389(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.393(2) . ?
C22 H20 0.9500 . ?
C23 H19 0.9500 . ?

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
C6 N1 C5 120.64(13) . . ?
C6 N1 C13 119.48(13) . . ?
C5 N1 C13 119.14(12) . . ?
C17 C1 C2 61.40(11) . . ?
C17 C1 H26 117.6 . . ?
C2 C1 H26 117.6 . . ?
C17 C1 H25 117.6 . . ?
C2 C1 H25 117.6 . . ?
H26 C1 H25 114.7 . . ?
C3 C2 C1 120.00(14) . . ?
C3 C2 C17 115.83(14) . . ?
C1 C2 C17 58.42(12) . . ?
C3 C2 H17 116.6 . . ?
C1 C2 H17 116.6 . . ?
C17 C2 H17 116.6 . . ?
O2 C3 C4 123.82(15) . . ?
O2 C3 C2 121.92(15) . . ?
C4 C3 C2 114.16(13) . . ?
C5 C4 C3 126.95(14) . . ?
C5 C4 H18 116.5 . . ?
C3 C4 H18 116.5 . . ?
C4 C5 N1 122.06(14) . . ?
C4 C5 C18 121.51(14) . . ?
N1 C5 C18 116.41(13) . . ?
O1 C6 N1 122.90(15) . . ?
O1 C6 C7 117.05(14) . . ?
N1 C6 C7 119.99(14) . . ?
C8 C7 C11 119.18(15) . . ?
C8 C7 C6 123.08(14) . . ?
C11 C7 C6 117.01(14) . . ?
C9 C8 C7 120.17(15) . . ?
C9 C8 H3 119.9 . . ?
C7 C8 H3 119.9 . . ?
C8 C9 C10 120.53(15) . . ?
C8 C9 H24 119.7 . . ?
C10 C9 H24 119.7 . . ?
C12 C10 C9 119.30(16) . . ?
C12 C10 H2 120.4 . . ?
C9 C10 H2 120.4 . . ?
C12 C11 C7 120.42(15) . . ?
C12 C11 H5 119.8 . . ?
C7 C11 H5 119.8 . . ?
C11 C12 C10 120.40(15) . . ?
C11 C12 H4 119.8 . . ?
C10 C12 H4 119.8 . . ?
C15 C13 N1 109.76(13) . . ?
C15 C13 C14 109.24(16) . . ?
N1 C13 C14 109.43(14) . . ?
C15 C13 C16 110.49(16) . . ?
N1 C13 C16 110.15(14) . . ?
C14 C13 C16 107.74(17) . . ?
C13 C14 H7 109.5 . . ?
C13 C14 H6 109.5 . . ?
H7 C14 H6 109.5 . . ?
C13 C14 H8 109.5 . . ?
H7 C14 H8 109.5 . . ?
H6 C14 H8 109.5 . . ?
C13 C15 H9 109.5 . . ?
C13 C15 H11 109.5 . . ?
H9 C15 H11 109.5 . . ?
C13 C15 H10 109.5 . . ?
H9 C15 H10 109.5 . . ?
H11 C15 H10 109.5 . . ?
C13 C16 H14 109.5 . . ?
C13 C16 H12 109.5 . . ?
H14 C16 H12 109.5 . . ?
C13 C16 H13 109.5 . . ?
H14 C16 H13 109.5 . . ?
H12 C16 H13 109.5 . . ?
C1 C17 C2 60.17(11) . . ?
C1 C17 H16 117.8 . . ?
C2 C17 H16 117.8 . . ?
C1 C17 H15 117.8 . . ?
C2 C17 H15 117.8 . . ?
H16 C17 H15 114.9 . . ?
C23 C18 C19 117.79(15) . . ?
C23 C18 C5 120.96(14) . . ?
C19 C18 C5 121.25(15) . . ?
C20 C19 C18 120.66(16) . . ?
C20 C19 H23 119.7 . . ?
C18 C19 H23 119.7 . . ?
C21 C20 C19 120.71(16) . . ?
C21 C20 H22 119.6 . . ?
C19 C20 H22 119.6 . . ?
C20 C21 C22 119.65(15) . . ?
C20 C21 H21 120.2 . . ?
C22 C21 H21 120.2 . . ?
C21 C22 C23 120.11(16) . . ?
C21 C22 H20 119.9 . . ?
C23 C22 H20 119.9 . . ?
C22 C23 C18 121.07(15) . . ?
C22 C23 H19 119.5 . . ?
C18 C23 H19 119.5 . . ?

_refine_diff_density_max         0.494
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.108

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_160222LT
_database_code_depnum_ccdc_archive 'CCDC 1529471'
_audit_update_record             
;
2017-01-24 deposited with the CCDC.
2017-05-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H24 F3 N O2'
_chemical_formula_weight         451.47

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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   14.9856(13)
_cell_length_b                   10.6591(8)
_cell_length_c                   14.4299(13)
_cell_angle_alpha                90
_cell_angle_beta                 93.353(4)
_cell_angle_gamma                90
_cell_volume                     2301.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3526
_cell_measurement_theta_min      2.6980
_cell_measurement_theta_max      25.4499

_exptl_crystal_description       Tabullar
_exptl_crystal_colour            'Pale Yellow'
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_F_000             944
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.098
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8372
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            17841
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.361
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4693
_reflns_number_gt                3235
_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, 2010)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_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)+(0.1235P)²+0.8520P] 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         4693
_refine_ls_number_parameters     301
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0947
_refine_ls_R_factor_gt           0.0631
_refine_ls_wR_factor_ref         0.2198
_refine_ls_wR_factor_gt          0.1869
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.001
_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
F1 F 1.09546(15) 0.1308(2) 0.4356(2) 0.0865(9) Uani 1 1 d . . . . .
F2 F 1.05521(16) 0.2767(4) 0.34875(18) 0.1116(12) Uani 1 1 d . . . . .
F3 F 1.12440(13) 0.3182(2) 0.47573(18) 0.0727(7) Uani 1 1 d . . . . .
O1 O 0.68483(12) 0.36006(18) 0.83416(12) 0.0309(5) Uani 1 1 d . . . . .
O2 O 0.54609(12) 0.21452(18) 0.68203(12) 0.0313(5) Uani 1 1 d . . . . .
N1 N 0.70927(14) 0.35557(19) 0.67894(14) 0.0218(5) Uani 1 1 d . . . . .
C1 C 0.8074(3) -0.0705(3) 0.8139(2) 0.0469(9) Uani 1 1 d . . . . .
H1 H 0.8287 -0.1513 0.8254 0.056 Uiso 1 1 calc R U . . .
C2 C 0.8631(2) 0.0194(3) 0.7816(2) 0.0444(8) Uani 1 1 d . . . . .
H21 H 0.9222 -0.0008 0.7715 0.053 Uiso 1 1 calc R U . . .
C3 C 0.8322(2) 0.1404(3) 0.76373(19) 0.0358(7) Uani 1 1 d . . . . .
H22 H 0.8705 0.2012 0.7425 0.043 Uiso 1 1 calc R U . . .
C4 C 0.74337(19) 0.1702(3) 0.77770(17) 0.0290(6) Uani 1 1 d . . . . .
C5 C 0.70908(17) 0.3030(3) 0.76593(17) 0.0258(6) Uani 1 1 d . . . . .
C6 C 0.71816(16) 0.2740(2) 0.59985(16) 0.0223(5) Uani 1 1 d . . . . .
C7 C 0.64826(17) 0.2086(2) 0.56273(17) 0.0249(6) Uani 1 1 d . . . . .
H16 H 0.6574 0.1640 0.5087 0.030 Uiso 1 1 calc R U . . .
C8 C 0.55784(17) 0.2004(2) 0.59944(17) 0.0249(6) Uani 1 1 d . . . . .
C9 C 0.48027(17) 0.1717(2) 0.53216(17) 0.0233(6) Uani 1 1 d . . . . .
C10 C 0.48943(17) 0.1615(2) 0.43713(18) 0.0248(6) Uani 1 1 d . . . . .
H15 H 0.5446 0.1749 0.4125 0.030 Uiso 1 1 calc R U . . .
C11 C 0.41451(18) 0.1309(2) 0.37883(19) 0.0300(6) Uani 1 1 d . . . . .
H14 H 0.4200 0.1233 0.3152 0.036 Uiso 1 1 calc R U . . .
C12 C 0.33209(18) 0.1118(2) 0.41576(19) 0.0289(6) Uani 1 1 d . . . . .
H2 H 0.2826 0.0905 0.3771 0.035 Uiso 1 1 calc R U . . .
C13 C 0.7196(3) -0.0415(3) 0.82949(19) 0.0445(8) Uani 1 1 d . . . . .
H24 H 0.6820 -0.1027 0.8515 0.053 Uiso 1 1 calc R U . . .
C14 C 0.6874(2) 0.0799(3) 0.81225(18) 0.0341(7) Uani 1 1 d . . . . .
H23 H 0.6287 0.1001 0.8239 0.041 Uiso 1 1 calc R U . . .
C15 C 0.67540(17) 0.4900(2) 0.66299(17) 0.0247(6) Uani 1 1 d . . . . .
C16 C 0.57841(18) 0.5028(3) 0.69033(19) 0.0305(6) Uani 1 1 d . . . . .
H4 H 0.5604 0.5891 0.6854 0.046 Uiso 1 1 calc R U . . .
H3 H 0.5740 0.4748 0.7531 0.046 Uiso 1 1 calc R U . . .
H5 H 0.5402 0.4526 0.6496 0.046 Uiso 1 1 calc R U . . .
C17 C 0.6791(2) 0.5239(3) 0.56063(18) 0.0319(6) Uani 1 1 d . . . . .
H6 H 0.6391 0.4706 0.5242 0.048 Uiso 1 1 calc R U . . .
H8 H 0.7390 0.5126 0.5417 0.048 Uiso 1 1 calc R U . . .
H7 H 0.6617 0.6099 0.5516 0.048 Uiso 1 1 calc R U . . .
C18 C 0.73663(18) 0.5792(3) 0.72104(19) 0.0318(6) Uani 1 1 d . . . . .
H11 H 0.7966 0.5724 0.7016 0.048 Uiso 1 1 calc R U . . .
H9 H 0.7356 0.5572 0.7855 0.048 Uiso 1 1 calc R U . . .
H10 H 0.7160 0.6639 0.7123 0.048 Uiso 1 1 calc R U . . .
C19 C 0.32374(18) 0.1246(2) 0.51040(19) 0.0286(6) Uani 1 1 d . . . . .
H12 H 0.2683 0.1131 0.5349 0.034 Uiso 1 1 calc R U . . .
C20 C 0.39685(18) 0.1540(2) 0.56846(18) 0.0263(6) Uani 1 1 d . . . . .
H13 H 0.3907 0.1621 0.6319 0.032 Uiso 1 1 calc R U . . .
C21 C 0.80755(16) 0.2668(2) 0.55964(17) 0.0221(5) Uani 1 1 d . . . . .
C22 C 0.82743(18) 0.1701(2) 0.49868(18) 0.0278(6) Uani 1 1 d . . . . .
H17 H 0.7842 0.1100 0.4830 0.033 Uiso 1 1 calc R U . . .
C23 C 0.90968(18) 0.1622(3) 0.4615(2) 0.0320(6) Uani 1 1 d . . . . .
H20 H 0.9215 0.0969 0.4214 0.038 Uiso 1 1 calc R U . . .
C24 C 0.97520(17) 0.2513(3) 0.48357(19) 0.0302(6) Uani 1 1 d . . . . .
C25 C 0.95783(18) 0.3459(3) 0.5462(2) 0.0334(7) Uani 1 1 d . . . . .
H19 H 1.0019 0.4043 0.5631 0.040 Uiso 1 1 calc R U . . .
C26 C 0.87479(18) 0.3531(3) 0.5836(2) 0.0315(6) Uani 1 1 d . . . . .
H18 H 0.8638 0.4168 0.6255 0.038 Uiso 1 1 calc R U . . .
C27 C 1.0627(2) 0.2449(3) 0.4384(2) 0.0424(8) 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
F1 C27 1.313(4) . ?
F2 C27 1.335(4) . ?
F3 C27 1.303(4) . ?
O1 C5 1.230(3) . ?
O2 C8 1.224(3) . ?
N1 C5 1.375(3) . ?
N1 C6 1.447(3) . ?
N1 C15 1.533(3) . ?
C1 C2 1.371(5) . ?
C1 C13 1.382(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.390(4) . ?
C2 H21 0.9300 . ?
C3 C4 1.394(4) . ?
C3 H22 0.9300 . ?
C4 C14 1.388(4) . ?
C4 C5 1.512(4) . ?
C6 C7 1.343(4) . ?
C6 C21 1.493(3) . ?
C7 C8 1.486(4) . ?
C7 H16 0.9300 . ?
C8 C9 1.502(4) . ?
C9 C10 1.390(4) . ?
C9 C20 1.396(4) . ?
C10 C11 1.402(4) . ?
C10 H15 0.9300 . ?
C11 C12 1.388(4) . ?
C11 H14 0.9300 . ?
C12 C19 1.385(4) . ?
C12 H2 0.9300 . ?
C13 C14 1.399(4) . ?
C13 H24 0.9300 . ?
C14 H23 0.9300 . ?
C15 C17 1.525(4) . ?
C15 C16 1.534(4) . ?
C15 C18 1.536(4) . ?
C16 H4 0.9600 . ?
C16 H3 0.9600 . ?
C16 H5 0.9600 . ?
C17 H6 0.9600 . ?
C17 H8 0.9600 . ?
C17 H7 0.9600 . ?
C18 H11 0.9600 . ?
C18 H9 0.9600 . ?
C18 H10 0.9600 . ?
C19 C20 1.376(4) . ?
C19 H12 0.9300 . ?
C20 H13 0.9300 . ?
C21 C26 1.393(4) . ?
C21 C22 1.399(4) . ?
C22 C23 1.375(4) . ?
C22 H17 0.9300 . ?
C23 C24 1.389(4) . ?
C23 H20 0.9300 . ?
C24 C25 1.389(4) . ?
C24 C27 1.499(4) . ?
C25 C26 1.387(4) . ?
C25 H19 0.9300 . ?
C26 H18 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
C5 N1 C6 118.7(2) . . ?
C5 N1 C15 120.0(2) . . ?
C6 N1 C15 119.21(18) . . ?
C2 C1 C13 120.2(3) . . ?
C2 C1 H1 119.9 . . ?
C13 C1 H1 119.9 . . ?
C1 C2 C3 120.6(3) . . ?
C1 C2 H21 119.7 . . ?
C3 C2 H21 119.7 . . ?
C2 C3 C4 119.7(3) . . ?
C2 C3 H22 120.1 . . ?
C4 C3 H22 120.1 . . ?
C14 C4 C3 119.7(3) . . ?
C14 C4 C5 118.7(3) . . ?
C3 C4 C5 121.2(2) . . ?
O1 C5 N1 123.1(2) . . ?
O1 C5 C4 119.2(2) . . ?
N1 C5 C4 117.7(2) . . ?
C7 C6 N1 121.4(2) . . ?
C7 C6 C21 121.0(2) . . ?
N1 C6 C21 117.6(2) . . ?
C6 C7 C8 126.5(2) . . ?
C6 C7 H16 116.8 . . ?
C8 C7 H16 116.8 . . ?
O2 C8 C7 121.7(2) . . ?
O2 C8 C9 120.3(2) . . ?
C7 C8 C9 118.0(2) . . ?
C10 C9 C20 120.1(2) . . ?
C10 C9 C8 122.4(2) . . ?
C20 C9 C8 117.5(2) . . ?
C9 C10 C11 119.2(2) . . ?
C9 C10 H15 120.4 . . ?
C11 C10 H15 120.4 . . ?
C12 C11 C10 120.2(2) . . ?
C12 C11 H14 119.9 . . ?
C10 C11 H14 119.9 . . ?
C19 C12 C11 119.8(2) . . ?
C19 C12 H2 120.1 . . ?
C11 C12 H2 120.1 . . ?
C1 C13 C14 120.0(3) . . ?
C1 C13 H24 120.0 . . ?
C14 C13 H24 120.0 . . ?
C4 C14 C13 119.7(3) . . ?
C4 C14 H23 120.1 . . ?
C13 C14 H23 120.1 . . ?
C17 C15 N1 109.7(2) . . ?
C17 C15 C16 108.5(2) . . ?
N1 C15 C16 110.8(2) . . ?
C17 C15 C18 109.1(2) . . ?
N1 C15 C18 108.4(2) . . ?
C16 C15 C18 110.4(2) . . ?
C15 C16 H4 109.5 . . ?
C15 C16 H3 109.5 . . ?
H4 C16 H3 109.5 . . ?
C15 C16 H5 109.5 . . ?
H4 C16 H5 109.5 . . ?
H3 C16 H5 109.5 . . ?
C15 C17 H6 109.5 . . ?
C15 C17 H8 109.5 . . ?
H6 C17 H8 109.5 . . ?
C15 C17 H7 109.5 . . ?
H6 C17 H7 109.5 . . ?
H8 C17 H7 109.5 . . ?
C15 C18 H11 109.5 . . ?
C15 C18 H9 109.5 . . ?
H11 C18 H9 109.5 . . ?
C15 C18 H10 109.5 . . ?
H11 C18 H10 109.5 . . ?
H9 C18 H10 109.5 . . ?
C20 C19 C12 120.5(3) . . ?
C20 C19 H12 119.7 . . ?
C12 C19 H12 119.7 . . ?
C19 C20 C9 120.1(2) . . ?
C19 C20 H13 120.0 . . ?
C9 C20 H13 120.0 . . ?
C26 C21 C22 117.7(2) . . ?
C26 C21 C6 121.5(2) . . ?
C22 C21 C6 120.8(2) . . ?
C23 C22 C21 121.3(2) . . ?
C23 C22 H17 119.4 . . ?
C21 C22 H17 119.4 . . ?
C22 C23 C24 120.5(2) . . ?
C22 C23 H20 119.8 . . ?
C24 C23 H20 119.8 . . ?
C25 C24 C23 119.2(3) . . ?
C25 C24 C27 121.2(2) . . ?
C23 C24 C27 119.6(2) . . ?
C26 C25 C24 120.0(2) . . ?
C26 C25 H19 120.0 . . ?
C24 C25 H19 120.0 . . ?
C25 C26 C21 121.3(2) . . ?
C25 C26 H18 119.4 . . ?
C21 C26 H18 119.4 . . ?
F3 C27 F1 108.0(3) . . ?
F3 C27 F2 105.4(3) . . ?
F1 C27 F2 102.5(3) . . ?
F3 C27 C24 114.2(3) . . ?
F1 C27 C24 113.2(3) . . ?
F2 C27 C24 112.6(3) . . ?

_refine_diff_density_max         0.941
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.102

_shelxl_version_number           2014/6

