# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_sample1
_database_code_depnum_ccdc_archive 'CCDC 1854136'
_audit_update_record             
;
2018-07-06 deposited with the CCDC.
2018-08-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
(2R*,3R*)-N-Benzyl-2-((S*)-1-hydroxy-2,2-dimethylpropyl)-3-(trifluoromethyl)glutarimide
_chemical_name_common            ?
_chemical_melting_point          397.0-398.2
_chemical_formula_moiety         'C18 H22 F3 N O3'
_chemical_formula_sum            'C18 H22 F3 N O3'
_chemical_formula_weight         357.36

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'
F F 0.0171 0.0103 '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      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                   16.4371(9)
_cell_length_b                   9.2127(4)
_cell_length_c                   24.4070(13)
_cell_angle_alpha                90
_cell_angle_beta                 109.415(6)
_cell_angle_gamma                90
_cell_volume                     3485.8(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6065
_cell_measurement_theta_min      2.3670
_cell_measurement_theta_max      27.3260

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_F_000             1504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_exptl_absorpt_coefficient_mu    0.113
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.99174
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.967
_oxdiff_exptl_absorpt_empirical_full_max 1.096
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30579
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.381
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6476
_reflns_number_gt                4632
_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       
;
CrystalClear-SM Auto 2.0 r1 (Rigaku, 2009)
;
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    
;
SHELXT-2014/5 (Sheldrick, 2014)
;
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    
;
Yadokari-XG 2014 (Wakita, Nemoto, et al., 2016)
;
_computing_publication_material  
;
Yadokari-XG 2014 (Wakita, Nemoto, et al., 2016)
;
_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)+(0.0401P)²+0.8858P] 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         6476
_refine_ls_number_parameters     459
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.0969
_refine_ls_wR_factor_gt          0.0846
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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 0.27918(8) 0.76317(11) 0.46649(4) 0.0535(3) Uani 1 1 d . . . . .
F2 F 0.22016(8) 0.16810(13) 0.83477(4) 0.0567(3) Uani 1 1 d . . . . .
F3 F 0.28647(8) 0.62148(12) 0.39910(5) 0.0602(3) Uani 1 1 d . . . . .
F4 F 0.21876(8) 0.02062(11) 0.76660(5) 0.0598(3) Uani 1 1 d . . . . .
O1 O 0.28192(7) 0.07762(12) 0.63293(5) 0.0381(3) Uani 1 1 d . . . . .
F5 F 0.33890(8) 0.10588(14) 0.82264(5) 0.0641(3) Uani 1 1 d . . . . .
O2 O 0.46511(8) 0.58387(13) 0.57366(5) 0.0419(3) Uani 1 1 d . . . . .
O3 O 0.21190(8) 0.68657(13) 0.59941(5) 0.0428(3) Uani 1 1 d . . . . .
O4 O 0.03100(8) 0.19892(14) 0.65872(6) 0.0469(3) Uani 1 1 d . . . . .
F6 F 0.16348(8) 0.67590(14) 0.40631(5) 0.0716(4) Uani 1 1 d . . . . .
O5 O 0.35517(9) 0.31914(12) 0.59189(5) 0.0433(3) Uani 1 1 d . . . . .
H1 H 0.344105 0.239447 0.604585 0.065 Uiso 1 1 calc R U . . .
O6 O 0.12272(9) 0.47070(13) 0.63966(5) 0.0477(3) Uani 1 1 d . . . . .
H2 H 0.142568 0.542430 0.627000 0.071 Uiso 1 1 calc R U . . .
N1 N 0.15655(8) 0.13600(14) 0.64555(6) 0.0293(3) Uani 1 1 d . . . . .
N2 N 0.33776(8) 0.64183(13) 0.58486(5) 0.0293(3) Uani 1 1 d . . . . .
C1 C 0.15564(10) 0.31424(17) 0.72307(7) 0.0316(4) Uani 1 1 d . . . . .
H3 H 0.124796 0.311285 0.752127 0.038 Uiso 1 1 calc R U . . .
C2 C 0.34212(10) 0.46405(16) 0.50834(7) 0.0290(4) Uani 1 1 d . . . . .
H4 H 0.374821 0.463312 0.480347 0.035 Uiso 1 1 calc R U . . .
C3 C 0.15275(11) 0.47394(17) 0.70153(7) 0.0325(4) Uani 1 1 d . . . . .
H5 H 0.213294 0.511379 0.714589 0.039 Uiso 1 1 calc R U . . .
C4 C 0.10821(11) 0.21350(17) 0.67368(7) 0.0316(4) Uani 1 1 d . . . . .
C5 C 0.34172(11) 0.30648(17) 0.53127(7) 0.0303(4) Uani 1 1 d . . . . .
H6 H 0.282466 0.266257 0.512388 0.036 Uiso 1 1 calc R U . . .
C6 C 0.38813(11) 0.56639(17) 0.55765(7) 0.0299(4) Uani 1 1 d . . . . .
C7 C 0.25015(11) 0.62702(17) 0.57024(7) 0.0323(4) Uani 1 1 d . . . . .
C8 C 0.24438(10) 0.14543(17) 0.66028(7) 0.0296(4) Uani 1 1 d . . . . .
C9 C 0.25002(11) 0.51278(18) 0.47542(7) 0.0337(4) Uani 1 1 d . . . . .
H7 H 0.220698 0.430599 0.449632 0.040 Uiso 1 1 calc R U . . .
C10 C 0.20213(11) 0.53739(19) 0.51835(7) 0.0362(4) Uani 1 1 d . . . . .
H8 H 0.146536 0.585676 0.497780 0.043 Uiso 1 1 calc R U . . .
H9 H 0.188966 0.441815 0.531957 0.043 Uiso 1 1 calc R U . . .
C11 C 0.10329(11) 0.09324(18) 0.53866(7) 0.0344(4) Uani 1 1 d . . . . .
C12 C 0.39420(11) 0.68100(18) 0.69216(7) 0.0335(4) Uani 1 1 d . . . . .
C13 C 0.38124(12) 0.74214(18) 0.63256(7) 0.0364(4) Uani 1 1 d . . . . .
H10 H 0.346711 0.832231 0.627626 0.044 Uiso 1 1 calc R U . . .
H11 H 0.438192 0.768411 0.629865 0.044 Uiso 1 1 calc R U . . .
C14 C 0.11109(11) 0.03572(18) 0.59805(7) 0.0355(4) Uani 1 1 d . . . . .
H12 H 0.052587 0.016870 0.599578 0.043 Uiso 1 1 calc R U . . .
H13 H 0.142432 -0.057874 0.604159 0.043 Uiso 1 1 calc R U . . .
C15 C 0.40579(10) 0.20124(17) 0.51825(7) 0.0309(4) Uani 1 1 d . . . . .
C16 C 0.29367(11) 0.24160(19) 0.70980(7) 0.0355(4) Uani 1 1 d . . . . .
H14 H 0.303660 0.336261 0.693921 0.043 Uiso 1 1 calc R U . . .
H15 H 0.350733 0.197158 0.729661 0.043 Uiso 1 1 calc R U . . .
C17 C 0.24903(11) 0.26821(18) 0.75438(7) 0.0339(4) Uani 1 1 d . . . . .
H16 H 0.278878 0.351918 0.778977 0.041 Uiso 1 1 calc R U . . .
C18 C 0.49855(11) 0.2536(2) 0.54466(8) 0.0396(4) Uani 1 1 d . . . . .
H17 H 0.511205 0.272893 0.586152 0.059 Uiso 1 1 calc R U . . .
H18 H 0.506253 0.342957 0.525127 0.059 Uiso 1 1 calc R U . . .
H19 H 0.537880 0.178790 0.539678 0.059 Uiso 1 1 calc R U . . .
C19 C 0.39578(12) 0.05300(18) 0.54390(8) 0.0404(4) Uani 1 1 d . . . . .
H20 H 0.431427 -0.018838 0.532794 0.061 Uiso 1 1 calc R U . . .
H21 H 0.335179 0.022936 0.528949 0.061 Uiso 1 1 calc R U . . .
H22 H 0.414333 0.060185 0.586340 0.061 Uiso 1 1 calc R U . . .
C20 C 0.09901(11) 0.57661(19) 0.72581(7) 0.0376(4) Uani 1 1 d . . . . .
C21 C 0.24470(12) 0.6426(2) 0.43710(8) 0.0420(4) Uani 1 1 d . . . . .
C22 C 0.13810(12) 0.0159(2) 0.50318(7) 0.0424(4) Uani 1 1 d . . . . .
H23 H 0.168165 -0.072016 0.517003 0.051 Uiso 1 1 calc R U . . .
C23 C 0.44021(12) 0.5547(2) 0.71098(8) 0.0446(5) Uani 1 1 d . . . . .
H24 H 0.463309 0.503064 0.685823 0.053 Uiso 1 1 calc R U . . .
C24 C 0.38102(12) 0.1852(2) 0.45221(7) 0.0441(5) Uani 1 1 d . . . . .
H25 H 0.389979 0.277932 0.435347 0.066 Uiso 1 1 calc R U . . .
H26 H 0.320203 0.157198 0.435796 0.066 Uiso 1 1 calc R U . . .
H27 H 0.417056 0.110375 0.443248 0.066 Uiso 1 1 calc R U . . .
C25 C 0.36187(12) 0.7540(2) 0.72981(8) 0.0456(5) Uani 1 1 d . . . . .
H28 H 0.329935 0.840864 0.717332 0.055 Uiso 1 1 calc R U . . .
C26 C 0.00451(12) 0.5320(2) 0.70618(9) 0.0504(5) Uani 1 1 d . . . . .
H29 H -0.028425 0.603215 0.720039 0.076 Uiso 1 1 calc R U . . .
H30 H -0.000719 0.436223 0.722190 0.076 Uiso 1 1 calc R U . . .
H31 H -0.018157 0.527684 0.663654 0.076 Uiso 1 1 calc R U . . .
C27 C 0.45273(13) 0.5033(2) 0.76654(8) 0.0546(5) Uani 1 1 d . . . . .
H32 H 0.484082 0.415922 0.779155 0.065 Uiso 1 1 calc R U . . .
C28 C 0.05954(12) 0.2211(2) 0.51768(8) 0.0456(5) Uani 1 1 d . . . . .
H33 H 0.034871 0.275742 0.541201 0.055 Uiso 1 1 calc R U . . .
C29 C 0.25670(12) 0.1404(2) 0.79418(8) 0.0430(4) Uani 1 1 d . . . . .
C30 C 0.12991(13) 0.0641(2) 0.44808(8) 0.0518(5) Uani 1 1 d . . . . .
H34 H 0.153876 0.009295 0.424201 0.062 Uiso 1 1 calc R U . . .
C31 C 0.05182(13) 0.2691(2) 0.46218(9) 0.0538(5) Uani 1 1 d . . . . .
H35 H 0.021796 0.356724 0.447845 0.065 Uiso 1 1 calc R U . . .
C32 C 0.08741(13) 0.1905(2) 0.42794(8) 0.0531(5) Uani 1 1 d . . . . .
H36 H 0.082372 0.224349 0.390184 0.064 Uiso 1 1 calc R U . . .
C33 C 0.10727(13) 0.72970(19) 0.70379(9) 0.0482(5) Uani 1 1 d . . . . .
H37 H 0.081970 0.731806 0.661339 0.072 Uiso 1 1 calc R U . . .
H38 H 0.168348 0.756557 0.715345 0.072 Uiso 1 1 calc R U . . .
H39 H 0.076776 0.798720 0.720595 0.072 Uiso 1 1 calc R U . . .
C34 C 0.42031(13) 0.5772(2) 0.80347(8) 0.0549(5) Uani 1 1 d . . . . .
H40 H 0.429190 0.541185 0.841498 0.066 Uiso 1 1 calc R U . . .
C35 C 0.37510(13) 0.7030(2) 0.78534(8) 0.0550(5) Uani 1 1 d . . . . .
H41 H 0.352891 0.755136 0.810849 0.066 Uiso 1 1 calc R U . . .
C36 C 0.13720(15) 0.5771(2) 0.79241(8) 0.0584(6) Uani 1 1 d . . . . .
H42 H 0.107916 0.650762 0.808047 0.088 Uiso 1 1 calc R U . . .
H43 H 0.198939 0.599399 0.804323 0.088 Uiso 1 1 calc R U . . .
H44 H 0.129129 0.481371 0.807360 0.088 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
F1 C21 1.341(2) . ?
F2 C29 1.343(2) . ?
F3 C21 1.339(2) . ?
F4 C29 1.334(2) . ?
O1 C8 1.2209(18) . ?
F5 C29 1.336(2) . ?
O2 C6 1.2046(19) . ?
O3 C7 1.2251(19) . ?
O4 C4 1.2058(19) . ?
F6 C21 1.332(2) . ?
O5 C5 1.4262(19) . ?
O5 H1 0.8400 . ?
O6 C3 1.4244(19) . ?
O6 H2 0.8400 . ?
N1 C8 1.370(2) . ?
N1 C4 1.405(2) . ?
N1 C14 1.476(2) . ?
N2 C7 1.370(2) . ?
N2 C6 1.405(2) . ?
N2 C13 1.472(2) . ?
C1 C4 1.516(2) . ?
C1 C17 1.530(2) . ?
C1 C3 1.558(2) . ?
C1 H3 1.0000 . ?
C2 C6 1.518(2) . ?
C2 C9 1.527(2) . ?
C2 C5 1.557(2) . ?
C2 H4 1.0000 . ?
C3 C20 1.541(2) . ?
C3 H5 1.0000 . ?
C5 C15 1.540(2) . ?
C5 H6 1.0000 . ?
C7 C10 1.498(2) . ?
C8 C16 1.500(2) . ?
C9 C21 1.503(2) . ?
C9 C10 1.522(2) . ?
C9 H7 1.0000 . ?
C10 H8 0.9900 . ?
C10 H9 0.9900 . ?
C11 C22 1.384(2) . ?
C11 C28 1.386(2) . ?
C11 C14 1.508(2) . ?
C12 C25 1.380(2) . ?
C12 C23 1.380(2) . ?
C12 C13 1.507(2) . ?
C13 H10 0.9900 . ?
C13 H11 0.9900 . ?
C14 H12 0.9900 . ?
C14 H13 0.9900 . ?
C15 C18 1.523(2) . ?
C15 C24 1.533(2) . ?
C15 C19 1.534(2) . ?
C16 C17 1.521(2) . ?
C16 H14 0.9900 . ?
C16 H15 0.9900 . ?
C17 C29 1.505(2) . ?
C17 H16 1.0000 . ?
C18 H17 0.9800 . ?
C18 H18 0.9800 . ?
C18 H19 0.9800 . ?
C19 H20 0.9800 . ?
C19 H21 0.9800 . ?
C19 H22 0.9800 . ?
C20 C26 1.522(3) . ?
C20 C33 1.531(3) . ?
C20 C36 1.535(2) . ?
C22 C30 1.380(3) . ?
C22 H23 0.9500 . ?
C23 C27 1.386(3) . ?
C23 H24 0.9500 . ?
C24 H25 0.9800 . ?
C24 H26 0.9800 . ?
C24 H27 0.9800 . ?
C25 C35 1.381(3) . ?
C25 H28 0.9500 . ?
C26 H29 0.9800 . ?
C26 H30 0.9800 . ?
C26 H31 0.9800 . ?
C27 C34 1.371(3) . ?
C27 H32 0.9500 . ?
C28 C31 1.390(3) . ?
C28 H33 0.9500 . ?
C30 C32 1.363(3) . ?
C30 H34 0.9500 . ?
C31 C32 1.375(3) . ?
C31 H35 0.9500 . ?
C32 H36 0.9500 . ?
C33 H37 0.9800 . ?
C33 H38 0.9800 . ?
C33 H39 0.9800 . ?
C34 C35 1.369(3) . ?
C34 H40 0.9500 . ?
C35 H41 0.9500 . ?
C36 H42 0.9800 . ?
C36 H43 0.9800 . ?
C36 H44 0.9800 . ?

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 O5 H1 109.5 . . ?
C3 O6 H2 109.5 . . ?
C8 N1 C4 123.87(14) . . ?
C8 N1 C14 117.38(13) . . ?
C4 N1 C14 118.74(13) . . ?
C7 N2 C6 124.11(14) . . ?
C7 N2 C13 117.41(13) . . ?
C6 N2 C13 118.48(13) . . ?
C4 C1 C17 113.14(13) . . ?
C4 C1 C3 111.10(13) . . ?
C17 C1 C3 110.08(13) . . ?
C4 C1 H3 107.4 . . ?
C17 C1 H3 107.4 . . ?
C3 C1 H3 107.4 . . ?
C6 C2 C9 112.35(13) . . ?
C6 C2 C5 110.78(13) . . ?
C9 C2 C5 109.97(13) . . ?
C6 C2 H4 107.9 . . ?
C9 C2 H4 107.9 . . ?
C5 C2 H4 107.9 . . ?
O6 C3 C20 112.32(14) . . ?
O6 C3 C1 107.39(13) . . ?
C20 C3 C1 114.02(13) . . ?
O6 C3 H5 107.6 . . ?
C20 C3 H5 107.6 . . ?
C1 C3 H5 107.6 . . ?
O4 C4 N1 120.30(15) . . ?
O4 C4 C1 121.36(15) . . ?
N1 C4 C1 118.34(14) . . ?
O5 C5 C15 112.62(13) . . ?
O5 C5 C2 106.20(12) . . ?
C15 C5 C2 115.35(12) . . ?
O5 C5 H6 107.4 . . ?
C15 C5 H6 107.4 . . ?
C2 C5 H6 107.4 . . ?
O2 C6 N2 120.06(15) . . ?
O2 C6 C2 122.21(15) . . ?
N2 C6 C2 117.74(14) . . ?
O3 C7 N2 120.13(16) . . ?
O3 C7 C10 120.67(15) . . ?
N2 C7 C10 119.19(14) . . ?
O1 C8 N1 120.29(15) . . ?
O1 C8 C16 120.45(15) . . ?
N1 C8 C16 119.25(14) . . ?
C21 C9 C10 111.93(14) . . ?
C21 C9 C2 113.82(14) . . ?
C10 C9 C2 109.31(13) . . ?
C21 C9 H7 107.1 . . ?
C10 C9 H7 107.1 . . ?
C2 C9 H7 107.1 . . ?
C7 C10 C9 114.60(14) . . ?
C7 C10 H8 108.6 . . ?
C9 C10 H8 108.6 . . ?
C7 C10 H9 108.6 . . ?
C9 C10 H9 108.6 . . ?
H8 C10 H9 107.6 . . ?
C22 C11 C28 118.58(16) . . ?
C22 C11 C14 119.98(16) . . ?
C28 C11 C14 121.42(16) . . ?
C25 C12 C23 118.61(16) . . ?
C25 C12 C13 119.90(16) . . ?
C23 C12 C13 121.47(16) . . ?
N2 C13 C12 113.85(13) . . ?
N2 C13 H10 108.8 . . ?
C12 C13 H10 108.8 . . ?
N2 C13 H11 108.8 . . ?
C12 C13 H11 108.8 . . ?
H10 C13 H11 107.7 . . ?
N1 C14 C11 113.21(13) . . ?
N1 C14 H12 108.9 . . ?
C11 C14 H12 108.9 . . ?
N1 C14 H13 108.9 . . ?
C11 C14 H13 108.9 . . ?
H12 C14 H13 107.8 . . ?
C18 C15 C24 110.73(14) . . ?
C18 C15 C19 109.73(14) . . ?
C24 C15 C19 108.46(14) . . ?
C18 C15 C5 111.72(14) . . ?
C24 C15 C5 108.46(13) . . ?
C19 C15 C5 107.63(13) . . ?
C8 C16 C17 114.31(14) . . ?
C8 C16 H14 108.7 . . ?
C17 C16 H14 108.7 . . ?
C8 C16 H15 108.7 . . ?
C17 C16 H15 108.7 . . ?
H14 C16 H15 107.6 . . ?
C29 C17 C16 112.25(14) . . ?
C29 C17 C1 113.22(14) . . ?
C16 C17 C1 109.26(13) . . ?
C29 C17 H16 107.3 . . ?
C16 C17 H16 107.3 . . ?
C1 C17 H16 107.3 . . ?
C15 C18 H17 109.5 . . ?
C15 C18 H18 109.5 . . ?
H17 C18 H18 109.5 . . ?
C15 C18 H19 109.5 . . ?
H17 C18 H19 109.5 . . ?
H18 C18 H19 109.5 . . ?
C15 C19 H20 109.5 . . ?
C15 C19 H21 109.5 . . ?
H20 C19 H21 109.5 . . ?
C15 C19 H22 109.5 . . ?
H20 C19 H22 109.5 . . ?
H21 C19 H22 109.5 . . ?
C26 C20 C33 109.79(15) . . ?
C26 C20 C36 110.45(16) . . ?
C33 C20 C36 108.43(16) . . ?
C26 C20 C3 111.62(15) . . ?
C33 C20 C3 107.54(14) . . ?
C36 C20 C3 108.91(15) . . ?
F6 C21 F3 106.93(15) . . ?
F6 C21 F1 106.11(15) . . ?
F3 C21 F1 105.56(15) . . ?
F6 C21 C9 111.97(15) . . ?
F3 C21 C9 112.21(15) . . ?
F1 C21 C9 113.54(14) . . ?
C30 C22 C11 121.14(18) . . ?
C30 C22 H23 119.4 . . ?
C11 C22 H23 119.4 . . ?
C12 C23 C27 120.04(18) . . ?
C12 C23 H24 120.0 . . ?
C27 C23 H24 120.0 . . ?
C15 C24 H25 109.5 . . ?
C15 C24 H26 109.5 . . ?
H25 C24 H26 109.5 . . ?
C15 C24 H27 109.5 . . ?
H25 C24 H27 109.5 . . ?
H26 C24 H27 109.5 . . ?
C12 C25 C35 121.19(18) . . ?
C12 C25 H28 119.4 . . ?
C35 C25 H28 119.4 . . ?
C20 C26 H29 109.5 . . ?
C20 C26 H30 109.5 . . ?
H29 C26 H30 109.5 . . ?
C20 C26 H31 109.5 . . ?
H29 C26 H31 109.5 . . ?
H30 C26 H31 109.5 . . ?
C34 C27 C23 120.65(19) . . ?
C34 C27 H32 119.7 . . ?
C23 C27 H32 119.7 . . ?
C11 C28 C31 119.91(19) . . ?
C11 C28 H33 120.0 . . ?
C31 C28 H33 120.0 . . ?
F4 C29 F5 106.73(15) . . ?
F4 C29 F2 106.30(15) . . ?
F5 C29 F2 106.53(14) . . ?
F4 C29 C17 113.37(14) . . ?
F5 C29 C17 112.04(15) . . ?
F2 C29 C17 111.43(15) . . ?
C32 C30 C22 119.9(2) . . ?
C32 C30 H34 120.0 . . ?
C22 C30 H34 120.0 . . ?
C32 C31 C28 120.33(19) . . ?
C32 C31 H35 119.8 . . ?
C28 C31 H35 119.8 . . ?
C30 C32 C31 120.10(19) . . ?
C30 C32 H36 119.9 . . ?
C31 C32 H36 119.9 . . ?
C20 C33 H37 109.5 . . ?
C20 C33 H38 109.5 . . ?
H37 C33 H38 109.5 . . ?
C20 C33 H39 109.5 . . ?
H37 C33 H39 109.5 . . ?
H38 C33 H39 109.5 . . ?
C35 C34 C27 119.73(18) . . ?
C35 C34 H40 120.1 . . ?
C27 C34 H40 120.1 . . ?
C34 C35 C25 119.78(19) . . ?
C34 C35 H41 120.1 . . ?
C25 C35 H41 120.1 . . ?
C20 C36 H42 109.5 . . ?
C20 C36 H43 109.5 . . ?
H42 C36 H43 109.5 . . ?
C20 C36 H44 109.5 . . ?
H42 C36 H44 109.5 . . ?
H43 C36 H44 109.5 . . ?

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
C4 C1 C3 O6 -12.61(18) . . . . ?
C17 C1 C3 O6 113.52(15) . . . . ?
C4 C1 C3 C20 112.50(16) . . . . ?
C17 C1 C3 C20 -121.37(15) . . . . ?
C8 N1 C4 O4 -179.35(15) . . . . ?
C14 N1 C4 O4 -0.7(2) . . . . ?
C8 N1 C4 C1 0.3(2) . . . . ?
C14 N1 C4 C1 178.98(13) . . . . ?
C17 C1 C4 O4 152.45(16) . . . . ?
C3 C1 C4 O4 -83.13(19) . . . . ?
C17 C1 C4 N1 -27.2(2) . . . . ?
C3 C1 C4 N1 97.19(17) . . . . ?
C6 C2 C5 O5 21.25(17) . . . . ?
C9 C2 C5 O5 -103.54(14) . . . . ?
C6 C2 C5 C15 -104.26(16) . . . . ?
C9 C2 C5 C15 130.95(14) . . . . ?
C7 N2 C6 O2 -178.88(14) . . . . ?
C13 N2 C6 O2 0.4(2) . . . . ?
C7 N2 C6 C2 1.0(2) . . . . ?
C13 N2 C6 C2 -179.68(13) . . . . ?
C9 C2 C6 O2 -150.31(15) . . . . ?
C5 C2 C6 O2 86.26(18) . . . . ?
C9 C2 C6 N2 29.78(19) . . . . ?
C5 C2 C6 N2 -93.65(16) . . . . ?
C6 N2 C7 O3 173.43(14) . . . . ?
C13 N2 C7 O3 -5.9(2) . . . . ?
C6 N2 C7 C10 -6.6(2) . . . . ?
C13 N2 C7 C10 174.15(14) . . . . ?
C4 N1 C8 O1 -178.14(14) . . . . ?
C14 N1 C8 O1 3.2(2) . . . . ?
C4 N1 C8 C16 1.0(2) . . . . ?
C14 N1 C8 C16 -177.68(14) . . . . ?
C6 C2 C9 C21 73.24(17) . . . . ?
C5 C2 C9 C21 -162.88(13) . . . . ?
C6 C2 C9 C10 -52.72(17) . . . . ?
C5 C2 C9 C10 71.16(16) . . . . ?
O3 C7 C10 C9 160.48(15) . . . . ?
N2 C7 C10 C9 -19.5(2) . . . . ?
C21 C9 C10 C7 -78.87(18) . . . . ?
C2 C9 C10 C7 48.17(19) . . . . ?
C7 N2 C13 C12 77.71(18) . . . . ?
C6 N2 C13 C12 -101.62(17) . . . . ?
C25 C12 C13 N2 -123.53(17) . . . . ?
C23 C12 C13 N2 58.4(2) . . . . ?
C8 N1 C14 C11 -75.40(18) . . . . ?
C4 N1 C14 C11 105.87(17) . . . . ?
C22 C11 C14 N1 121.01(17) . . . . ?
C28 C11 C14 N1 -60.8(2) . . . . ?
O5 C5 C15 C18 -62.55(17) . . . . ?
C2 C5 C15 C18 59.58(18) . . . . ?
O5 C5 C15 C24 175.13(13) . . . . ?
C2 C5 C15 C24 -62.75(18) . . . . ?
O5 C5 C15 C19 57.98(17) . . . . ?
C2 C5 C15 C19 -179.89(14) . . . . ?
O1 C8 C16 C17 -155.83(15) . . . . ?
N1 C8 C16 C17 25.0(2) . . . . ?
C8 C16 C17 C29 76.90(19) . . . . ?
C8 C16 C17 C1 -49.56(19) . . . . ?
C4 C1 C17 C29 -75.59(17) . . . . ?
C3 C1 C17 C29 159.43(13) . . . . ?
C4 C1 C17 C16 50.31(18) . . . . ?
C3 C1 C17 C16 -74.66(16) . . . . ?
O6 C3 C20 C26 59.45(19) . . . . ?
C1 C3 C20 C26 -63.00(19) . . . . ?
O6 C3 C20 C33 -61.03(19) . . . . ?
C1 C3 C20 C33 176.52(14) . . . . ?
O6 C3 C20 C36 -178.34(15) . . . . ?
C1 C3 C20 C36 59.2(2) . . . . ?
C10 C9 C21 F6 -59.53(19) . . . . ?
C2 C9 C21 F6 175.90(14) . . . . ?
C10 C9 C21 F3 -179.79(14) . . . . ?
C2 C9 C21 F3 55.64(19) . . . . ?
C10 C9 C21 F1 60.6(2) . . . . ?
C2 C9 C21 F1 -64.0(2) . . . . ?
C28 C11 C22 C30 0.1(3) . . . . ?
C14 C11 C22 C30 178.29(17) . . . . ?
C25 C12 C23 C27 0.3(3) . . . . ?
C13 C12 C23 C27 178.44(17) . . . . ?
C23 C12 C25 C35 0.2(3) . . . . ?
C13 C12 C25 C35 -177.92(17) . . . . ?
C12 C23 C27 C34 -0.5(3) . . . . ?
C22 C11 C28 C31 -0.3(3) . . . . ?
C14 C11 C28 C31 -178.46(16) . . . . ?
C16 C17 C29 F4 -62.8(2) . . . . ?
C1 C17 C29 F4 61.5(2) . . . . ?
C16 C17 C29 F5 58.10(19) . . . . ?
C1 C17 C29 F5 -177.61(14) . . . . ?
C16 C17 C29 F2 177.35(14) . . . . ?
C1 C17 C29 F2 -58.36(19) . . . . ?
C11 C22 C30 C32 0.4(3) . . . . ?
C11 C28 C31 C32 0.0(3) . . . . ?
C22 C30 C32 C31 -0.8(3) . . . . ?
C28 C31 C32 C30 0.6(3) . . . . ?
C23 C27 C34 C35 0.0(3) . . . . ?
C27 C34 C35 C25 0.5(3) . . . . ?
C12 C25 C35 C34 -0.6(3) . . . . ?

_refine_diff_density_max         0.198
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.033

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1854137'
_audit_update_record             
;
2018-07-06 deposited with the CCDC.
2018-08-06 downloaded from the CCDC.
;
_audit_creation_date             2015-10-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        
'(2R*,3R*)-N-Benzyl-2- ((S*)-1-hydroxy-3-phenylpropyl)-3-(trifluoromethyl)glutarimide'
_chemical_formula_moiety         'C22 H22 F3 N O3'
_chemical_formula_sum            'C22 H22 F3 N O3'
_chemical_formula_weight         405.40
_chemical_melting_point          369.8-375.3
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'
F F 0.0171 0.0103 '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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.8654(11)
_cell_length_b                   10.7372(12)
_cell_length_c                   11.1375(13)
_cell_angle_alpha                66.630(5)
_cell_angle_beta                 79.912(6)
_cell_angle_gamma                63.756(5)
_cell_volume                     971.3(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8421
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.6
_cell_measurement_theta_min      3.0
_shelx_estimated_absorpt_T_max   0.951
_shelx_estimated_absorpt_T_min   0.944
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.854
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Prism
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.529
_exptl_crystal_size_mid          0.483
_exptl_crystal_size_min          0.457
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9629
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_min         3.044
_diffrn_ambient_temperature      293
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
scan:
	Number of images: 180
	           Slice: -60.0000 - 120.0000
	     Image width: 1.0000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 0.0000
	             XTD: 50.0000
	          2theta: 30.0000
scan:
	Number of images: 180
	           Slice: -60.0000 - 120.0000
	     Image width: 1.0000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 120.0000
	             XTD: 50.0000
	          2theta: 30.0000
scan:
	Number of images: 180
	           Slice: -60.0000 - 120.0000
	     Image width: 1.0000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 240.0000
	             XTD: 50.0000
	          2theta: 30.0000
;
_diffrn_measurement_device       
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  
;
Rigaku Mercury375R (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.072645
_diffrn_orient_matrix_UB_12      -0.031508
_diffrn_orient_matrix_UB_13      -0.079267
_diffrn_orient_matrix_UB_21      0.017618
_diffrn_orient_matrix_UB_22      0.109810
_diffrn_orient_matrix_UB_23      0.004061
_diffrn_orient_matrix_UB_31      0.071381
_diffrn_orient_matrix_UB_32      -0.044717
_diffrn_orient_matrix_UB_33      -0.048210
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           12.0
_diffrn_source_power             0.6
_diffrn_source_voltage           50.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3659
_reflns_number_total             4416
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrystalClear-SM Auto 2.0 r1 (Rigaku, 2009)
;
_computing_data_collection       
;
CrystalClear-SM Auto 2.0 r1 (Rigaku, 2009)
;
_computing_data_reduction        
;
CrystalClear-SM Auto 2.0 r1 (Rigaku, 2009)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4416
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0415
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0400P)²+0.3295P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0969
_refine_ls_wR_factor_ref         0.1031
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12), C16(H16), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C11(H11A,H11B), C17(H17A,H17B), C25(H25A,H25B)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C19(H19), C20(H20), C21(H21), C23(H23), C24(H24), C26(H26),
 C27(H27), C28(H28), C29(H29)
2.d Idealised tetrahedral OH refined as rotating group:
 O7(H7)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.37715(10) 0.17439(11) 0.35857(9) 0.0366(2) Uani 1 1 d . . . . .
O2 O -0.13131(11) 0.36381(11) 0.39911(10) 0.0388(2) Uani 1 1 d . . . . .
F3 F 0.15092(11) -0.04309(10) 0.54318(9) 0.0493(2) Uani 1 1 d . . . . .
N4 N 0.12239(12) 0.26673(12) 0.37942(10) 0.0275(2) Uani 1 1 d . . . . .
F5 F 0.26718(13) -0.15757(11) 0.72661(11) 0.0665(3) Uani 1 1 d . . . . .
C6 C 0.26858(14) 0.18983(13) 0.43102(12) 0.0274(3) Uani 1 1 d . . . . .
O7 O 0.23672(15) 0.37799(12) 0.54121(13) 0.0581(4) Uani 1 1 d . . . . .
H7 H 0.2354 0.4345 0.5742 0.087 Uiso 1 1 calc GR . . . .
C8 C 0.00497(15) 0.24106(18) 0.59846(14) 0.0392(3) Uani 1 1 d . . . . .
H8A H -0.0800 0.2169 0.6390 0.047 Uiso 1 1 calc R . . . .
H8B H -0.0013 0.3216 0.6216 0.047 Uiso 1 1 calc R . . . .
F9 F 0.02413(13) -0.05381(14) 0.72105(11) 0.0695(3) Uani 1 1 d . . . . .
C10 C -0.00892(14) 0.29459(14) 0.45290(13) 0.0299(3) Uani 1 1 d . . . . .
C11 C 0.10442(15) 0.32527(15) 0.23566(12) 0.0319(3) Uani 1 1 d . . . . .
H11A H 0.0260 0.3052 0.2156 0.038 Uiso 1 1 calc R . . . .
H11B H 0.1980 0.2729 0.1977 0.038 Uiso 1 1 calc R . . . .
C12 C 0.28840(14) 0.12788(14) 0.57836(12) 0.0278(3) Uani 1 1 d . . . . .
H12 H 0.3740 0.0300 0.6012 0.033 Uiso 1 1 calc R . . . .
C13 C 0.06403(14) 0.49016(15) 0.17370(12) 0.0288(3) Uani 1 1 d . . . . .
C14 C -0.07693(16) 0.58675(16) 0.11681(13) 0.0357(3) Uani 1 1 d . . . . .
H14 H -0.1472 0.5495 0.1205 0.043 Uiso 1 1 calc R . . . .
C15 C 0.52874(16) 0.28672(16) 0.76369(14) 0.0353(3) Uani 1 1 d . . . . .
C16 C 0.33247(15) 0.22960(15) 0.61536(13) 0.0317(3) Uani 1 1 d . . . . .
H16 H 0.3112 0.2127 0.7085 0.038 Uiso 1 1 calc R . . . .
C17 C 0.49834(16) 0.19784(18) 0.59104(15) 0.0387(3) Uani 1 1 d . . . . .
H17A H 0.5207 0.2096 0.4998 0.046 Uiso 1 1 calc R . . . .
H17B H 0.5580 0.0950 0.6435 0.046 Uiso 1 1 calc R . . . .
C18 C 0.15100(15) 0.10513(16) 0.65473(13) 0.0343(3) Uani 1 1 d . . . . .
H18 H 0.1605 0.0952 0.7445 0.041 Uiso 1 1 calc R . . . .
C19 C -0.11448(19) 0.73762(17) 0.05479(14) 0.0442(4) Uani 1 1 d . . . . .
H19 H -0.2095 0.8012 0.0172 0.053 Uiso 1 1 calc R . . . .
C20 C 0.45764(17) 0.41476(18) 0.79353(16) 0.0427(4) Uani 1 1 d . . . . .
H20 H 0.4203 0.5070 0.7261 0.051 Uiso 1 1 calc R . . . .
C21 C 0.16694(17) 0.54774(17) 0.16880(15) 0.0392(3) Uani 1 1 d . . . . .
H21 H 0.2613 0.4846 0.2079 0.047 Uiso 1 1 calc R . . . .
C22 C 0.14818(18) -0.03667(18) 0.66130(15) 0.0433(4) Uani 1 1 d . . . . .
C23 C 0.58317(19) 0.15086(18) 0.86658(16) 0.0450(4) Uani 1 1 d . . . . .
H23 H 0.6320 0.0633 0.8491 0.054 Uiso 1 1 calc R . . . .
C24 C 0.1298(2) 0.6988(2) 0.10596(16) 0.0493(4) Uani 1 1 d . . . . .
H24 H 0.1997 0.7365 0.1023 0.059 Uiso 1 1 calc R . . . .
C25 C 0.5462(2) 0.2982(2) 0.62288(15) 0.0460(4) Uani 1 1 d . . . . .
H25A H 0.6515 0.2753 0.5985 0.055 Uiso 1 1 calc R . . . .
H25B H 0.4876 0.4006 0.5688 0.055 Uiso 1 1 calc R . . . .
C26 C 0.4945(2) 0.2722(3) 1.02232(17) 0.0563(5) Uani 1 1 d . . . . .
H26 H 0.4824 0.2672 1.1086 0.068 Uiso 1 1 calc R . . . .
C27 C -0.0107(2) 0.79365(18) 0.04868(15) 0.0488(4) Uani 1 1 d . . . . .
H27 H -0.0352 0.8950 0.0062 0.059 Uiso 1 1 calc R . . . .
C28 C 0.44110(19) 0.4082(2) 0.92124(19) 0.0532(4) Uani 1 1 d . . . . .
H28 H 0.3939 0.4955 0.9391 0.064 Uiso 1 1 calc R . . . .
C29 C 0.5659(2) 0.1438(2) 0.99442(17) 0.0548(5) Uani 1 1 d . . . . .
H29 H 0.6027 0.0518 1.0622 0.066 Uiso 1 1 calc R . . . .


_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 1.2133(16) . ?
O2 C10 1.2148(16) . ?
F3 C22 1.3394(18) . ?
N4 C6 1.3975(16) . ?
N4 C10 1.3847(17) . ?
N4 C11 1.4807(16) . ?
F5 C22 1.3397(18) . ?
C6 C12 1.5182(17) . ?
O7 C16 1.4182(16) . ?
C8 C10 1.4988(19) . ?
C8 C18 1.5263(19) . ?
F9 C22 1.3384(18) . ?
C11 C13 1.5075(19) . ?
C12 C16 1.5464(18) . ?
C12 C18 1.5312(18) . ?
C13 C14 1.3866(18) . ?
C13 C21 1.387(2) . ?
C14 C19 1.382(2) . ?
C15 C20 1.386(2) . ?
C15 C23 1.388(2) . ?
C15 C25 1.508(2) . ?
C16 C17 1.5140(19) . ?
C17 C25 1.523(2) . ?
C18 C22 1.507(2) . ?
C19 C27 1.379(3) . ?
C20 C28 1.380(2) . ?
C21 C24 1.385(2) . ?
C23 C29 1.380(2) . ?
C24 C27 1.383(3) . ?
C26 C28 1.378(3) . ?
C26 C29 1.378(3) . ?

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 N4 C11 118.39(10) . . ?
C10 N4 C6 124.81(11) . . ?
C10 N4 C11 116.79(10) . . ?
O1 C6 N4 120.15(11) . . ?
O1 C6 C12 121.00(11) . . ?
N4 C6 C12 118.85(11) . . ?
C10 C8 C18 114.27(11) . . ?
O2 C10 N4 120.11(12) . . ?
O2 C10 C8 121.62(12) . . ?
N4 C10 C8 118.25(11) . . ?
N4 C11 C13 113.10(10) . . ?
C6 C12 C16 108.44(11) . . ?
C6 C12 C18 113.50(10) . . ?
C18 C12 C16 112.64(11) . . ?
C14 C13 C11 119.82(12) . . ?
C14 C13 C21 118.84(13) . . ?
C21 C13 C11 121.32(12) . . ?
C19 C14 C13 120.93(14) . . ?
C20 C15 C23 117.88(14) . . ?
C20 C15 C25 119.92(14) . . ?
C23 C15 C25 122.20(14) . . ?
O7 C16 C12 106.17(10) . . ?
O7 C16 C17 112.49(13) . . ?
C17 C16 C12 111.99(11) . . ?
C16 C17 C25 113.87(12) . . ?
C8 C18 C12 110.84(11) . . ?
C22 C18 C8 112.23(12) . . ?
C22 C18 C12 111.48(12) . . ?
C27 C19 C14 119.86(15) . . ?
C28 C20 C15 121.35(16) . . ?
C24 C21 C13 120.31(14) . . ?
F3 C22 F5 106.07(14) . . ?
F3 C22 C18 113.03(12) . . ?
F5 C22 C18 112.02(12) . . ?
F9 C22 F3 106.12(12) . . ?
F9 C22 F5 106.91(13) . . ?
F9 C22 C18 112.22(14) . . ?
C29 C23 C15 120.92(16) . . ?
C27 C24 C21 120.23(15) . . ?
C15 C25 C17 115.97(13) . . ?
C29 C26 C28 119.41(16) . . ?
C19 C27 C24 119.83(15) . . ?
C26 C28 C20 120.01(17) . . ?
C26 C29 C23 120.42(17) . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1854140'
_audit_update_record             
;
2018-07-06 deposited with the CCDC.
2018-08-06 downloaded from the CCDC.
;
_audit_creation_date             2015-11-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
(2S*,3R*,4R*)-N-Benzyl-2-(tert-butyl)-tetrahydro-6-oxo-4-(trifluoromethyl)-2H-pyran-3-carboxamide
_chemical_formula_moiety         '2(C18 H22 F3 N O3)'
_chemical_formula_sum            'C36 H44 F6 N2 O6'
_chemical_formula_weight         714.73
_chemical_melting_point          468.7-470.9
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'
F F 0.0171 0.0103 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.0908(7)
_cell_length_b                   9.2610(6)
_cell_length_c                   16.8687(12)
_cell_angle_alpha                90
_cell_angle_beta                 94.711(7)
_cell_angle_gamma                90
_cell_volume                     1726.8(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    15487
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_shelx_estimated_absorpt_T_max   0.967
_shelx_estimated_absorpt_T_min   0.953
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.875
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Prism
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.424
_exptl_crystal_size_mid          0.343
_exptl_crystal_size_min          0.296
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17619
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         3.056
_diffrn_ambient_temperature      293
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
scan:
	Number of images: 180
	           Slice: -60.0000 - 120.0000
	     Image width: 1.0000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 0.0000
	             XTD: 50.0000
	          2theta: 30.0000
scan:
	Number of images: 180
	           Slice: -60.0000 - 120.0000
	     Image width: 1.0000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 120.0000
	             XTD: 50.0000
	          2theta: 30.0000
scan:
	Number of images: 180
	           Slice: -60.0000 - 120.0000
	     Image width: 1.0000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 240.0000
	             XTD: 50.0000
	          2theta: 30.0000
;
_diffrn_measurement_device       
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  
;
Rigaku Mercury375R (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.034031
_diffrn_orient_matrix_UB_12      -0.081761
_diffrn_orient_matrix_UB_13      0.018318
_diffrn_orient_matrix_UB_21      0.017176
_diffrn_orient_matrix_UB_22      -0.016440
_diffrn_orient_matrix_UB_23      -0.105293
_diffrn_orient_matrix_UB_31      0.056026
_diffrn_orient_matrix_UB_32      0.019147
_diffrn_orient_matrix_UB_33      0.006150
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           12.0
_diffrn_source_power             0.6
_diffrn_source_voltage           50.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3320
_reflns_number_total             3941
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrystalClear-SM Auto 2.0 r1 (Rigaku, 2009)
;
_computing_data_collection       
;
CrystalClear-SM Auto 2.0 r1 (Rigaku, 2009)
;
_computing_data_reduction        
;
CrystalClear-SM Auto 2.0 r1 (Rigaku, 2009)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3941
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0385
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0431P)²+0.5401P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.0974
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C11(H11), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C24(H24A,H24B)
2.c Aromatic/amide H refined with riding coordinates:
 N7(H7), C16(H16), C18(H18), C21(H21), C22(H22), C25(H25)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.80548(7) 0.14949(9) 0.19733(5) 0.02671(19) Uani 1 1 d . . . . .
O2 O 0.61264(8) -0.04558(9) 0.23472(6) 0.0322(2) Uani 1 1 d . . . . .
O3 O 0.92399(8) 0.07443(10) 0.29926(6) 0.0345(2) Uani 1 1 d . . . . .
F4 F 0.42990(8) 0.31979(13) 0.32233(5) 0.0605(3) Uani 1 1 d . . . . .
F5 F 0.56386(8) 0.33254(11) 0.42117(5) 0.0517(3) Uani 1 1 d . . . . .
F6 F 0.50402(9) 0.12660(11) 0.37590(6) 0.0528(3) Uani 1 1 d . . . . .
N7 N 0.42814(9) 0.03794(13) 0.19051(6) 0.0319(3) Uani 1 1 d . . . . .
H7 H 0.3863 0.1110 0.1728 0.038 Uiso 1 1 calc R . . . .
C8 C 0.70220(10) 0.23483(13) 0.16519(7) 0.0242(2) Uani 1 1 d . . . . .
H8 H 0.7254 0.3364 0.1725 0.029 Uiso 1 1 calc R . . . .
C9 C 0.74426(11) 0.18709(14) 0.33353(7) 0.0278(3) Uani 1 1 d . . . . .
H9A H 0.7874 0.2513 0.3714 0.033 Uiso 1 1 calc R . . . .
H9B H 0.7185 0.1042 0.3630 0.033 Uiso 1 1 calc R . . . .
C10 C 0.83154(11) 0.13555(13) 0.27603(7) 0.0257(2) Uani 1 1 d . . . . .
C11 C 0.63144(11) 0.26556(13) 0.29786(7) 0.0259(3) Uani 1 1 d . . . . .
H11 H 0.6536 0.3674 0.2928 0.031 Uiso 1 1 calc R . . . .
C12 C 0.54637(11) 0.05548(13) 0.21368(7) 0.0251(2) Uani 1 1 d . . . . .
C13 C 0.33146(11) -0.13717(15) 0.27700(7) 0.0300(3) Uani 1 1 d . . . . .
C14 C 0.59195(10) 0.21096(13) 0.21320(7) 0.0238(2) Uani 1 1 d . . . . .
H14 H 0.5259 0.2726 0.1907 0.029 Uiso 1 1 calc R . . . .
C15 C 0.53206(12) 0.25991(16) 0.35383(8) 0.0347(3) Uani 1 1 d . . . . .
C16 C 0.38250(12) -0.25242(17) 0.32019(8) 0.0374(3) Uani 1 1 d . . . . .
H16 H 0.4422 -0.3078 0.2992 0.045 Uiso 1 1 calc R . . . .
C17 C 0.68898(11) 0.20790(14) 0.07457(7) 0.0284(3) Uani 1 1 d . . . . .
C18 C 0.24335(13) -0.05519(15) 0.30968(9) 0.0380(3) Uani 1 1 d . . . . .
H18 H 0.2087 0.0226 0.2814 0.046 Uiso 1 1 calc R . . . .
C19 C 0.66945(14) 0.04897(15) 0.05226(8) 0.0381(3) Uani 1 1 d . . . . .
H19A H 0.7349 -0.0076 0.0766 0.057 Uiso 1 1 calc GR . . . .
H19B H 0.6666 0.0387 -0.0045 0.057 Uiso 1 1 calc GR . . . .
H19C H 0.5945 0.0162 0.0707 0.057 Uiso 1 1 calc GR . . . .
C20 C 0.58237(14) 0.29706(17) 0.03808(8) 0.0416(3) Uani 1 1 d . . . . .
H20A H 0.5081 0.2566 0.0534 0.062 Uiso 1 1 calc GR . . . .
H20B H 0.5822 0.2957 -0.0188 0.062 Uiso 1 1 calc GR . . . .
H20C H 0.5899 0.3948 0.0568 0.062 Uiso 1 1 calc GR . . . .
C21 C 0.25762(14) -0.20367(19) 0.42614(9) 0.0450(4) Uani 1 1 d . . . . .
H21 H 0.2328 -0.2261 0.4760 0.054 Uiso 1 1 calc R . . . .
C22 C 0.20653(14) -0.08792(17) 0.38396(9) 0.0431(4) Uani 1 1 d . . . . .
H22 H 0.1475 -0.0322 0.4055 0.052 Uiso 1 1 calc R . . . .
C23 C 0.80574(14) 0.26097(19) 0.04086(9) 0.0443(4) Uani 1 1 d . . . . .
H23A H 0.8185 0.3608 0.0543 0.067 Uiso 1 1 calc GR . . . .
H23B H 0.7986 0.2502 -0.0159 0.067 Uiso 1 1 calc GR . . . .
H23C H 0.8730 0.2050 0.0632 0.067 Uiso 1 1 calc GR . . . .
C24 C 0.36955(12) -0.10297(16) 0.19491(8) 0.0359(3) Uani 1 1 d . . . . .
H24A H 0.4249 -0.1771 0.1796 0.043 Uiso 1 1 calc R . . . .
H24B H 0.2988 -0.1052 0.1571 0.043 Uiso 1 1 calc R . . . .
C25 C 0.34520(14) -0.28567(19) 0.39435(9) 0.0460(4) Uani 1 1 d . . . . .
H25 H 0.3794 -0.3636 0.4228 0.055 Uiso 1 1 calc R . . . .


_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 C8 1.4590(14) . ?
O1 C10 1.3413(15) . ?
O2 C12 1.2244(15) . ?
O3 C10 1.2080(15) . ?
F4 C15 1.3322(16) . ?
F5 C15 1.3421(16) . ?
F6 C15 1.3337(18) . ?
N7 C12 1.3470(15) . ?
N7 C24 1.4624(17) . ?
C8 C14 1.5370(16) . ?
C8 C17 1.5439(16) . ?
C9 C10 1.5033(17) . ?
C9 C11 1.5272(17) . ?
C11 C14 1.5441(16) . ?
C11 C15 1.5099(17) . ?
C12 C14 1.5264(17) . ?
C13 C16 1.387(2) . ?
C13 C18 1.387(2) . ?
C13 C24 1.5142(18) . ?
C16 C25 1.384(2) . ?
C17 C19 1.5302(18) . ?
C17 C20 1.5294(18) . ?
C17 C23 1.5371(18) . ?
C18 C22 1.383(2) . ?
C21 C22 1.382(2) . ?
C21 C25 1.376(2) . ?

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
C10 O1 C8 121.24(9) . . ?
C12 N7 C24 121.26(11) . . ?
O1 C8 C14 111.14(9) . . ?
O1 C8 C17 106.76(9) . . ?
C14 C8 C17 118.91(10) . . ?
C10 C9 C11 116.56(10) . . ?
O1 C10 C9 120.68(10) . . ?
O3 C10 O1 118.31(11) . . ?
O3 C10 C9 120.92(11) . . ?
C9 C11 C14 111.69(10) . . ?
C15 C11 C9 110.72(10) . . ?
C15 C11 C14 113.63(10) . . ?
O2 C12 N7 122.60(12) . . ?
O2 C12 C14 122.11(10) . . ?
N7 C12 C14 115.29(11) . . ?
C16 C13 C18 118.89(13) . . ?
C16 C13 C24 120.60(13) . . ?
C18 C13 C24 120.50(13) . . ?
C8 C14 C11 105.23(9) . . ?
C12 C14 C8 114.62(10) . . ?
C12 C14 C11 111.90(9) . . ?
F4 C15 F5 106.55(12) . . ?
F4 C15 F6 106.65(12) . . ?
F4 C15 C11 112.13(11) . . ?
F5 C15 C11 110.94(11) . . ?
F6 C15 F5 106.19(11) . . ?
F6 C15 C11 113.92(11) . . ?
C25 C16 C13 120.44(14) . . ?
C19 C17 C8 113.51(10) . . ?
C19 C17 C23 108.85(12) . . ?
C20 C17 C8 108.58(10) . . ?
C20 C17 C19 109.34(11) . . ?
C20 C17 C23 108.99(11) . . ?
C23 C17 C8 107.47(10) . . ?
C22 C18 C13 120.68(14) . . ?
C25 C21 C22 120.00(14) . . ?
C21 C22 C18 119.83(14) . . ?
N7 C24 C13 113.05(11) . . ?
C21 C25 C16 120.16(15) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_TY3
_database_code_depnum_ccdc_archive 'CCDC 1854139'
_audit_update_record             
;
2018-07-06 deposited with the CCDC.
2018-08-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'(2R*,3R*)-N-Benzyl-2-((1R*,2S*)-1-hydroxy-2-(methoxymethoxy)-2-phenylethyl)-3-(trifluoromethyl)- glutarimide'
_chemical_name_common            ?
_chemical_melting_point          382.0-382.8
_chemical_formula_moiety         'C23 H24 F3 N O5'
_chemical_formula_sum            'C23 H24 F3 N O5'
_chemical_formula_weight         451.43

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'
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'
H H 0.0000 0.0000 '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                   9.9904(3)
_cell_length_b                   10.9743(3)
_cell_length_c                   19.9416(7)
_cell_angle_alpha                90
_cell_angle_beta                 98.589(3)
_cell_angle_gamma                90
_cell_volume                     2161.83(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    8022
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      27.65

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_F_000             944
_exptl_transmission_factor_min   0.980
_exptl_transmission_factor_max   0.989
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.114
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.84343
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.910
_oxdiff_exptl_absorpt_empirical_full_max 1.103
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27070
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.692
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4016
_reflns_number_gt                3227
_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       'CrystalClear-SM Expert 2.0 r1 (Rigaku, 2009)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    SHELXT2014
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
Yadokari-XG 2014 (Wakita, Nemoto, et al., 2016)
;
_computing_publication_material  
;
Yadokari-XG 2014 (Wakita, Nemoto, et al., 2016)
;

_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)+(0.0472P)²+0.5040P] 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         4016
_refine_ls_number_parameters     291
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0364
_refine_ls_wR_factor_ref         0.0972
_refine_ls_wR_factor_gt          0.0896
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_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 0.74975(10) 0.64787(9) 0.24117(5) 0.0384(3) Uani 1 1 d . . . . .
O2 O 0.50316(10) 0.71885(10) 0.26477(6) 0.0418(3) Uani 1 1 d . . . . .
H1 H 0.5474 0.7606 0.2404 0.063 Uiso 1 1 calc R U . . .
O3 O 0.44984(10) 0.40666(8) 0.32288(5) 0.0380(3) Uani 1 1 d . . . . .
F1 F 0.31927(11) 0.57551(10) 0.46534(5) 0.0604(3) Uani 1 1 d . . . . .
F2 F 0.51571(11) 0.63824(11) 0.51010(5) 0.0632(3) Uani 1 1 d . . . . .
O4 O 0.72176(12) 0.54500(10) 0.13775(6) 0.0491(3) Uani 1 1 d . . . . .
O5 O 0.11416(11) 0.68374(11) 0.28096(6) 0.0510(3) Uani 1 1 d . . . . .
F3 F 0.34756(13) 0.76164(12) 0.49837(6) 0.0793(4) Uani 1 1 d . . . . .
N1 N 0.27877(11) 0.54277(10) 0.30568(6) 0.0312(3) Uani 1 1 d . . . . .
C1 C 0.78448(14) 0.49943(13) 0.33249(7) 0.0334(3) Uani 1 1 d . . . . .
C2 C 0.41032(14) 0.50981(12) 0.33066(7) 0.0297(3) Uani 1 1 d . . . . .
C3 C 0.18894(15) 0.45277(12) 0.19260(7) 0.0338(3) Uani 1 1 d . . . . .
C4 C 0.68192(14) 0.56866(13) 0.28327(7) 0.0329(3) Uani 1 1 d . . . . .
H2 H 0.6229 0.5099 0.2541 0.040 Uiso 1 1 calc R U . . .
C5 C 0.50654(14) 0.60473(12) 0.36573(7) 0.0311(3) Uani 1 1 d . . . . .
H3 H 0.5689 0.5625 0.4023 0.037 Uiso 1 1 calc R U . . .
C6 C 0.18960(15) 0.45092(14) 0.26817(8) 0.0353(3) Uani 1 1 d . . . . .
H4 H 0.0960 0.4643 0.2774 0.042 Uiso 1 1 calc R U . . .
H5 H 0.2184 0.3691 0.2856 0.042 Uiso 1 1 calc R U . . .
C7 C 0.59370(14) 0.65899(12) 0.31576(7) 0.0333(3) Uani 1 1 d . . . . .
H6 H 0.6546 0.7219 0.3405 0.040 Uiso 1 1 calc R U . . .
C8 C 0.89112(16) 0.56066(15) 0.37059(8) 0.0433(4) Uani 1 1 d . . . . .
H7 H 0.8973 0.6468 0.3671 0.052 Uiso 1 1 calc R U . . .
C9 C 0.22546(15) 0.65960(13) 0.31108(8) 0.0365(3) Uani 1 1 d . . . . .
C10 C 0.08108(16) 0.39823(14) 0.15135(8) 0.0422(4) Uani 1 1 d . . . . .
H8 H 0.0101 0.3623 0.1714 0.051 Uiso 1 1 calc R U . . .
C11 C 0.29239(17) 0.50283(15) 0.16201(8) 0.0441(4) Uani 1 1 d . . . . .
H9 H 0.3675 0.5401 0.1891 0.053 Uiso 1 1 calc R U . . .
C12 C 0.81291(17) 0.58738(16) 0.19242(8) 0.0444(4) Uani 1 1 d . . . . .
H10 H 0.8776 0.6438 0.1755 0.053 Uiso 1 1 calc R U . . .
H11 H 0.8652 0.5176 0.2142 0.053 Uiso 1 1 calc R U . . .
C13 C 0.43498(15) 0.70741(13) 0.39928(8) 0.0386(4) Uani 1 1 d . . . . .
H12 H 0.4992 0.7777 0.4063 0.046 Uiso 1 1 calc R U . . .
C14 C 0.30695(16) 0.75252(14) 0.35420(9) 0.0423(4) Uani 1 1 d . . . . .
H13 H 0.2476 0.7910 0.3837 0.051 Uiso 1 1 calc R U . . .
H14 H 0.3336 0.8169 0.3240 0.051 Uiso 1 1 calc R U . . .
C15 C 0.77832(16) 0.37336(14) 0.33801(8) 0.0430(4) Uani 1 1 d . . . . .
H15 H 0.7060 0.3299 0.3123 0.052 Uiso 1 1 calc R U . . .
C16 C 0.07510(19) 0.39532(18) 0.08193(9) 0.0551(5) Uani 1 1 d . . . . .
H16 H 0.0001 0.3582 0.0546 0.066 Uiso 1 1 calc R U . . .
C17 C 0.98862(17) 0.49776(18) 0.41358(9) 0.0512(4) Uani 1 1 d . . . . .
H17 H 1.0607 0.5408 0.4398 0.061 Uiso 1 1 calc R U . . .
C18 C 0.2866(2) 0.49864(17) 0.09227(9) 0.0552(5) Uani 1 1 d . . . . .
H18 H 0.3584 0.5323 0.0719 0.066 Uiso 1 1 calc R U . . .
C19 C 0.98160(18) 0.37238(18) 0.41852(9) 0.0541(5) Uani 1 1 d . . . . .
H19 H 1.0489 0.3292 0.4479 0.065 Uiso 1 1 calc R U . . .
C20 C 0.1777(2) 0.44622(18) 0.05208(9) 0.0585(5) Uani 1 1 d . . . . .
H20 H 0.1733 0.4452 0.0042 0.070 Uiso 1 1 calc R U . . .
C21 C 0.40417(18) 0.67059(16) 0.46795(9) 0.0491(4) Uani 1 1 d . . . . .
C22 C 0.6532(2) 0.64062(19) 0.09896(9) 0.0604(5) Uani 1 1 d . . . . .
H21 H 0.5903 0.6804 0.1253 0.091 Uiso 1 1 calc R U . . .
H22 H 0.6026 0.6072 0.0571 0.091 Uiso 1 1 calc R U . . .
H23 H 0.7192 0.7003 0.0876 0.091 Uiso 1 1 calc R U . . .
C23 C 0.87688(18) 0.31055(16) 0.38075(10) 0.0543(5) Uani 1 1 d . . . . .
H24 H 0.8720 0.2243 0.3839 0.065 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 C12 1.4026(18) . ?
O1 C4 1.4455(17) . ?
O2 C7 1.4174(17) . ?
O2 H1 0.8400 . ?
O3 C2 1.2164(16) . ?
F1 C21 1.341(2) . ?
F2 C21 1.340(2) . ?
O4 C12 1.392(2) . ?
O4 C22 1.418(2) . ?
O5 C9 1.2115(18) . ?
F3 C21 1.3374(19) . ?
N1 C2 1.3823(18) . ?
N1 C9 1.3986(18) . ?
N1 C6 1.4731(18) . ?
C1 C8 1.386(2) . ?
C1 C15 1.390(2) . ?
C1 C4 1.513(2) . ?
C2 C5 1.5157(19) . ?
C3 C10 1.390(2) . ?
C3 C11 1.389(2) . ?
C3 C6 1.506(2) . ?
C4 C7 1.533(2) . ?
C4 H2 1.0000 . ?
C5 C7 1.538(2) . ?
C5 C13 1.5400(19) . ?
C5 H3 1.0000 . ?
C6 H4 0.9900 . ?
C6 H5 0.9900 . ?
C7 H6 1.0000 . ?
C8 C17 1.382(2) . ?
C8 H7 0.9500 . ?
C9 C14 1.494(2) . ?
C10 C16 1.377(2) . ?
C10 H8 0.9500 . ?
C11 C18 1.384(2) . ?
C11 H9 0.9500 . ?
C12 H10 0.9900 . ?
C12 H11 0.9900 . ?
C13 C21 1.503(2) . ?
C13 C14 1.532(2) . ?
C13 H12 1.0000 . ?
C14 H13 0.9900 . ?
C14 H14 0.9900 . ?
C15 C23 1.386(2) . ?
C15 H15 0.9500 . ?
C16 C20 1.378(3) . ?
C16 H16 0.9500 . ?
C17 C19 1.382(3) . ?
C17 H17 0.9500 . ?
C18 C20 1.377(3) . ?
C18 H18 0.9500 . ?
C19 C23 1.374(3) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C22 H21 0.9800 . ?
C22 H22 0.9800 . ?
C22 H23 0.9800 . ?
C23 H24 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
C12 O1 C4 114.60(11) . . ?
C7 O2 H1 109.5 . . ?
C12 O4 C22 112.72(13) . . ?
C2 N1 C9 124.38(12) . . ?
C2 N1 C6 118.31(11) . . ?
C9 N1 C6 117.26(12) . . ?
C8 C1 C15 118.59(14) . . ?
C8 C1 C4 120.17(13) . . ?
C15 C1 C4 121.16(13) . . ?
O3 C2 N1 120.45(13) . . ?
O3 C2 C5 120.18(13) . . ?
N1 C2 C5 119.33(12) . . ?
C10 C3 C11 118.18(14) . . ?
C10 C3 C6 118.27(13) . . ?
C11 C3 C6 123.52(14) . . ?
O1 C4 C1 110.36(11) . . ?
O1 C4 C7 101.86(11) . . ?
C1 C4 C7 115.27(12) . . ?
O1 C4 H2 109.7 . . ?
C1 C4 H2 109.7 . . ?
C7 C4 H2 109.7 . . ?
C2 C5 C7 110.40(11) . . ?
C2 C5 C13 113.56(12) . . ?
C7 C5 C13 110.04(11) . . ?
C2 C5 H3 107.5 . . ?
C7 C5 H3 107.5 . . ?
C13 C5 H3 107.5 . . ?
N1 C6 C3 114.25(12) . . ?
N1 C6 H4 108.7 . . ?
C3 C6 H4 108.7 . . ?
N1 C6 H5 108.7 . . ?
C3 C6 H5 108.7 . . ?
H4 C6 H5 107.6 . . ?
O2 C7 C4 110.01(12) . . ?
O2 C7 C5 106.37(11) . . ?
C4 C7 C5 116.13(11) . . ?
O2 C7 H6 108.0 . . ?
C4 C7 H6 108.0 . . ?
C5 C7 H6 108.0 . . ?
C17 C8 C1 120.70(16) . . ?
C17 C8 H7 119.7 . . ?
C1 C8 H7 119.7 . . ?
O5 C9 N1 119.61(14) . . ?
O5 C9 C14 121.12(14) . . ?
N1 C9 C14 119.27(13) . . ?
C16 C10 C3 121.23(16) . . ?
C16 C10 H8 119.4 . . ?
C3 C10 H8 119.4 . . ?
C18 C11 C3 120.38(16) . . ?
C18 C11 H9 119.8 . . ?
C3 C11 H9 119.8 . . ?
O4 C12 O1 113.06(13) . . ?
O4 C12 H10 109.0 . . ?
O1 C12 H10 109.0 . . ?
O4 C12 H11 109.0 . . ?
O1 C12 H11 109.0 . . ?
H10 C12 H11 107.8 . . ?
C21 C13 C14 110.79(13) . . ?
C21 C13 C5 111.75(13) . . ?
C14 C13 C5 112.50(12) . . ?
C21 C13 H12 107.2 . . ?
C14 C13 H12 107.2 . . ?
C5 C13 H12 107.2 . . ?
C9 C14 C13 116.91(12) . . ?
C9 C14 H13 108.1 . . ?
C13 C14 H13 108.1 . . ?
C9 C14 H14 108.1 . . ?
C13 C14 H14 108.1 . . ?
H13 C14 H14 107.3 . . ?
C23 C15 C1 120.53(15) . . ?
C23 C15 H15 119.7 . . ?
C1 C15 H15 119.7 . . ?
C10 C16 C20 120.09(17) . . ?
C10 C16 H16 120.0 . . ?
C20 C16 H16 120.0 . . ?
C8 C17 C19 120.18(16) . . ?
C8 C17 H17 119.9 . . ?
C19 C17 H17 119.9 . . ?
C20 C18 C11 120.65(17) . . ?
C20 C18 H18 119.7 . . ?
C11 C18 H18 119.7 . . ?
C23 C19 C17 119.70(16) . . ?
C23 C19 H19 120.2 . . ?
C17 C19 H19 120.2 . . ?
C18 C20 C16 119.45(17) . . ?
C18 C20 H20 120.3 . . ?
C16 C20 H20 120.3 . . ?
F3 C21 F2 106.37(13) . . ?
F3 C21 F1 106.93(14) . . ?
F2 C21 F1 106.27(14) . . ?
F3 C21 C13 111.74(15) . . ?
F2 C21 C13 112.25(14) . . ?
F1 C21 C13 112.85(13) . . ?
O4 C22 H21 109.5 . . ?
O4 C22 H22 109.5 . . ?
H21 C22 H22 109.5 . . ?
O4 C22 H23 109.5 . . ?
H21 C22 H23 109.5 . . ?
H22 C22 H23 109.5 . . ?
C19 C23 C15 120.30(17) . . ?
C19 C23 H24 119.9 . . ?
C15 C23 H24 119.9 . . ?

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
C9 N1 C2 O3 -178.69(13) . . . . ?
C6 N1 C2 O3 -1.50(19) . . . . ?
C9 N1 C2 C5 -0.8(2) . . . . ?
C6 N1 C2 C5 176.34(12) . . . . ?
C12 O1 C4 C1 71.96(15) . . . . ?
C12 O1 C4 C7 -165.14(12) . . . . ?
C8 C1 C4 O1 48.54(18) . . . . ?
C15 C1 C4 O1 -128.07(14) . . . . ?
C8 C1 C4 C7 -66.14(17) . . . . ?
C15 C1 C4 C7 117.25(15) . . . . ?
O3 C2 C5 C7 81.22(16) . . . . ?
N1 C2 C5 C7 -96.62(14) . . . . ?
O3 C2 C5 C13 -154.64(13) . . . . ?
N1 C2 C5 C13 27.51(18) . . . . ?
C2 N1 C6 C3 -92.23(15) . . . . ?
C9 N1 C6 C3 85.17(15) . . . . ?
C10 C3 C6 N1 -160.58(13) . . . . ?
C11 C3 C6 N1 21.4(2) . . . . ?
O1 C4 C7 O2 59.89(13) . . . . ?
C1 C4 C7 O2 179.37(11) . . . . ?
O1 C4 C7 C5 -179.27(11) . . . . ?
C1 C4 C7 C5 -59.78(16) . . . . ?
C2 C5 C7 O2 63.34(14) . . . . ?
C13 C5 C7 O2 -62.80(14) . . . . ?
C2 C5 C7 C4 -59.44(16) . . . . ?
C13 C5 C7 C4 174.43(12) . . . . ?
C15 C1 C8 C17 -0.5(2) . . . . ?
C4 C1 C8 C17 -177.25(14) . . . . ?
C2 N1 C9 O5 171.52(13) . . . . ?
C6 N1 C9 O5 -5.7(2) . . . . ?
C2 N1 C9 C14 -8.7(2) . . . . ?
C6 N1 C9 C14 174.11(13) . . . . ?
C11 C3 C10 C16 -1.0(2) . . . . ?
C6 C3 C10 C16 -179.15(15) . . . . ?
C10 C3 C11 C18 0.4(2) . . . . ?
C6 C3 C11 C18 178.41(15) . . . . ?
C22 O4 C12 O1 65.32(18) . . . . ?
C4 O1 C12 O4 74.92(16) . . . . ?
C2 C5 C13 C21 82.26(16) . . . . ?
C7 C5 C13 C21 -153.41(13) . . . . ?
C2 C5 C13 C14 -43.12(17) . . . . ?
C7 C5 C13 C14 81.21(15) . . . . ?
O5 C9 C14 C13 170.06(14) . . . . ?
N1 C9 C14 C13 -9.8(2) . . . . ?
C21 C13 C14 C9 -90.83(16) . . . . ?
C5 C13 C14 C9 35.07(19) . . . . ?
C8 C1 C15 C23 0.0(2) . . . . ?
C4 C1 C15 C23 176.68(15) . . . . ?
C3 C10 C16 C20 0.5(3) . . . . ?
C1 C8 C17 C19 0.7(3) . . . . ?
C3 C11 C18 C20 0.8(3) . . . . ?
C8 C17 C19 C23 -0.3(3) . . . . ?
C11 C18 C20 C16 -1.4(3) . . . . ?
C10 C16 C20 C18 0.7(3) . . . . ?
C14 C13 C21 F3 -56.50(18) . . . . ?
C5 C13 C21 F3 177.19(13) . . . . ?
C14 C13 C21 F2 -175.90(13) . . . . ?
C5 C13 C21 F2 57.79(18) . . . . ?
C14 C13 C21 F1 64.04(17) . . . . ?
C5 C13 C21 F1 -62.27(18) . . . . ?
C17 C19 C23 C15 -0.2(3) . . . . ?
C1 C15 C23 C19 0.4(3) . . . . ?

_refine_diff_density_max         0.167
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.032

####################################################################### 
# 
# 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_TY2
_database_code_depnum_ccdc_archive 'CCDC 1854138'
_audit_update_record             
;
2018-07-06 deposited with the CCDC.
2018-08-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
(2R*,3R*)-N-Benzyl-2-((1R*,2S*)-1-hydroxy-2-phenylpropyl)-3-(trifluoromethyl)glutarimide
_chemical_name_common            ?
_chemical_melting_point          408.7-409.4
_chemical_formula_moiety         'C22 H22 F3 N O3'
_chemical_formula_sum            'C22 H22 F3 N O3'
_chemical_formula_weight         405.40

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                   9.9948(5)
_cell_length_b                   23.4736(12)
_cell_length_c                   16.9093(9)
_cell_angle_alpha                90
_cell_angle_beta                 92.259(5)
_cell_angle_gamma                90
_cell_volume                     3964.1(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    8561
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      32.33

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_F_000             1696
_exptl_transmission_factor_min   0.984
_exptl_transmission_factor_max   0.989
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.109
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.94368
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.940
_oxdiff_exptl_absorpt_empirical_full_max 1.091
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            71529
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_av_R_equivalents  0.0974
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.039
_diffrn_reflns_theta_max         25.499
_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             7374
_reflns_number_gt                4546
_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       'CrystalClear-SM Expert 2.0 r1 (Rigaku, 2009)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT 2013'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
Yadokari-XG 2014 (Wakita, Nemoto, et al., 2016)
;
_computing_publication_material  
;
Yadokari-XG 2014 (Wakita, Nemoto, et al., 2016)
;

_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)+(0.0776P)²+0.0082P] 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         7374
_refine_ls_number_parameters     527
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0981
_refine_ls_R_factor_gt           0.0517
_refine_ls_wR_factor_ref         0.1536
_refine_ls_wR_factor_gt          0.1253
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_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
C1 C 0.1373(2) 0.89839(9) 0.35873(13) 0.0386(5) Uani 1 1 d . . . . .
C2 C 0.0303(2) 0.93471(10) 0.37042(15) 0.0524(6) Uani 1 1 d . . . . .
H1 H -0.0585 0.9214 0.3601 0.063 Uiso 1 1 calc R U . . .
C3 C 0.0506(3) 0.98952(11) 0.39661(17) 0.0649(8) Uani 1 1 d . . . . .
H2 H -0.0240 1.0135 0.4054 0.078 Uiso 1 1 calc R U . . .
C4 C 0.1780(3) 1.00975(12) 0.41010(19) 0.0727(8) Uani 1 1 d . . . . .
H3 H 0.1920 1.0479 0.4274 0.087 Uiso 1 1 calc R U . . .
C5 C 0.2851(3) 0.97483(12) 0.3986(2) 0.0762(9) Uani 1 1 d . . . . .
H4 H 0.3736 0.9888 0.4076 0.091 Uiso 1 1 calc R U . . .
C6 C 0.2645(2) 0.91925(11) 0.37384(16) 0.0582(7) Uani 1 1 d . . . . .
H5 H 0.3394 0.8950 0.3672 0.070 Uiso 1 1 calc R U . . .
C7 C 0.1155(2) 0.83917(10) 0.32645(13) 0.0421(5) Uani 1 1 d . . . . .
H6 H 0.2029 0.8185 0.3312 0.050 Uiso 1 1 calc R U . . .
C8 C 0.0733(3) 0.84206(11) 0.23863(14) 0.0612(7) Uani 1 1 d . . . . .
H7 H -0.0123 0.8622 0.2323 0.092 Uiso 1 1 calc R U . . .
H8 H 0.0634 0.8034 0.2175 0.092 Uiso 1 1 calc R U . . .
H9 H 0.1417 0.8624 0.2098 0.092 Uiso 1 1 calc R U . . .
C9 C 0.0137(2) 0.80546(9) 0.37206(13) 0.0430(6) Uani 1 1 d . . . . .
H10 H -0.0754 0.8246 0.3656 0.052 Uiso 1 1 calc R U . . .
O1 O 0.00313(19) 0.74947(7) 0.33966(11) 0.0623(5) Uani 1 1 d . . . . .
H11 H -0.0755 0.7440 0.3218 0.093 Uiso 1 1 calc R U . . .
C10 C 0.0515(2) 0.80060(9) 0.46205(13) 0.0400(5) Uani 1 1 d . . . . .
H12 H 0.1110 0.8336 0.4765 0.048 Uiso 1 1 calc R U . . .
C11 C -0.0722(2) 0.80481(10) 0.51200(14) 0.0445(6) Uani 1 1 d . . . . .
H13 H -0.1320 0.8345 0.4871 0.053 Uiso 1 1 calc R U . . .
C12 C -0.1492(2) 0.74886(10) 0.50936(16) 0.0535(7) Uani 1 1 d . . . . .
H14 H -0.2198 0.7505 0.5488 0.064 Uiso 1 1 calc R U . . .
H15 H -0.1942 0.7449 0.4564 0.064 Uiso 1 1 calc R U . . .
C13 C -0.0649(2) 0.69708(11) 0.52549(14) 0.0498(6) Uani 1 1 d . . . . .
N1 N 0.07017(19) 0.69929(8) 0.50625(11) 0.0442(5) Uani 1 1 d . . . . .
C14 C 0.1318(2) 0.74696(10) 0.47610(13) 0.0425(6) Uani 1 1 d . . . . .
C15 C -0.0396(3) 0.82360(10) 0.59490(15) 0.0526(6) Uani 1 1 d . . . . .
F1 F 0.02983(17) 0.87231(6) 0.59843(9) 0.0707(4) Uani 1 1 d . . . . .
F2 F -0.14955(18) 0.83280(8) 0.63566(10) 0.0848(5) Uani 1 1 d . . . . .
F3 F 0.03559(17) 0.78611(6) 0.63657(9) 0.0741(5) Uani 1 1 d . . . . .
O2 O -0.11038(19) 0.65409(8) 0.55285(12) 0.0692(5) Uani 1 1 d . . . . .
O3 O 0.24892(16) 0.74547(7) 0.46020(10) 0.0572(5) Uani 1 1 d . . . . .
C16 C 0.1508(3) 0.64710(10) 0.51957(15) 0.0532(7) Uani 1 1 d . . . . .
H16 H 0.1240 0.6290 0.5694 0.064 Uiso 1 1 calc R U . . .
H17 H 0.2463 0.6579 0.5263 0.064 Uiso 1 1 calc R U . . .
C17 C 0.1360(2) 0.60426(10) 0.45347(14) 0.0468(6) Uani 1 1 d . . . . .
C18 C 0.1452(3) 0.54676(11) 0.47094(17) 0.0594(7) Uani 1 1 d . . . . .
H18 H 0.1604 0.5350 0.5243 0.071 Uiso 1 1 calc R U . . .
C19 C 0.1326(3) 0.50619(12) 0.41204(19) 0.0673(8) Uani 1 1 d . . . . .
H19 H 0.1387 0.4669 0.4252 0.081 Uiso 1 1 calc R U . . .
C20 C 0.1112(3) 0.52240(12) 0.33470(18) 0.0653(8) Uani 1 1 d . . . . .
H20 H 0.1018 0.4945 0.2942 0.078 Uiso 1 1 calc R U . . .
C21 C 0.1034(3) 0.57920(12) 0.31614(16) 0.0617(7) Uani 1 1 d . . . . .
H21 H 0.0894 0.5906 0.2625 0.074 Uiso 1 1 calc R U . . .
C22 C 0.1158(2) 0.62012(11) 0.37491(15) 0.0528(6) Uani 1 1 d . . . . .
H22 H 0.1105 0.6593 0.3613 0.063 Uiso 1 1 calc R U . . .
C23 C 0.6212(2) 0.57828(11) 0.38699(14) 0.0492(6) Uani 1 1 d . . . . .
C24 C 0.7328(3) 0.56204(12) 0.34680(16) 0.0594(7) Uani 1 1 d . . . . .
H23 H 0.8011 0.5892 0.3380 0.071 Uiso 1 1 calc R U . . .
C25 C 0.7469(3) 0.50691(13) 0.31922(19) 0.0746(9) Uani 1 1 d . . . . .
H24 H 0.8237 0.4968 0.2910 0.089 Uiso 1 1 calc R U . . .
C26 C 0.6509(4) 0.46711(13) 0.3324(2) 0.0832(10) Uani 1 1 d . . . . .
H25 H 0.6600 0.4294 0.3131 0.100 Uiso 1 1 calc R U . . .
C27 C 0.5420(4) 0.48190(14) 0.37358(19) 0.0820(10) Uani 1 1 d . . . . .
H26 H 0.4764 0.4539 0.3841 0.098 Uiso 1 1 calc R U . . .
C28 C 0.5250(3) 0.53722(13) 0.40041(16) 0.0655(8) Uani 1 1 d . . . . .
H27 H 0.4473 0.5470 0.4280 0.079 Uiso 1 1 calc R U . . .
C29 C 0.6003(3) 0.63913(11) 0.41176(14) 0.0533(7) Uani 1 1 d . . . . .
H28 H 0.6873 0.6596 0.4068 0.064 Uiso 1 1 calc R U . . .
C30 C 0.5602(3) 0.64427(14) 0.49780(16) 0.0772(9) Uani 1 1 d . . . . .
H29 H 0.4736 0.6256 0.5041 0.116 Uiso 1 1 calc R U . . .
H30 H 0.5531 0.6846 0.5120 0.116 Uiso 1 1 calc R U . . .
H31 H 0.6282 0.6259 0.5325 0.116 Uiso 1 1 calc R U . . .
C31 C 0.4963(3) 0.66838(10) 0.35623(16) 0.0546(7) Uani 1 1 d . . . . .
H32 H 0.4101 0.6469 0.3581 0.065 Uiso 1 1 calc R U . . .
O4 O 0.4735(2) 0.72583(8) 0.37948(13) 0.0839(7) Uani 1 1 d . . . . .
H33 H 0.4072 0.7271 0.4085 0.126 Uiso 1 1 calc R U . . .
C32 C 0.4189(2) 0.67137(11) 0.21105(16) 0.0556(7) Uani 1 1 d . . . . .
H34 H 0.3517 0.6439 0.2312 0.067 Uiso 1 1 calc R U . . .
C33 C 0.5391(2) 0.67080(10) 0.26947(14) 0.0460(6) Uani 1 1 d . . . . .
H35 H 0.5926 0.6358 0.2591 0.055 Uiso 1 1 calc R U . . .
C34 C 0.6295(2) 0.72130(10) 0.26187(14) 0.0444(6) Uani 1 1 d . . . . .
N2 N 0.58019(19) 0.77062(8) 0.22703(11) 0.0466(5) Uani 1 1 d . . . . .
C35 C 0.4472(3) 0.77824(12) 0.20116(16) 0.0554(7) Uani 1 1 d . . . . .
C36 C 0.3534(3) 0.72954(11) 0.20829(19) 0.0669(8) Uani 1 1 d . . . . .
H36 H 0.2880 0.7306 0.1628 0.080 Uiso 1 1 calc R U . . .
H37 H 0.3029 0.7347 0.2570 0.080 Uiso 1 1 calc R U . . .
C37 C 0.4545(3) 0.65140(12) 0.13031(19) 0.0658(8) Uani 1 1 d . . . . .
F4 F 0.34705(19) 0.64684(8) 0.08130(12) 0.1013(6) Uani 1 1 d . . . . .
F5 F 0.5120(2) 0.60017(7) 0.13145(10) 0.0921(6) Uani 1 1 d . . . . .
F6 F 0.53856(18) 0.68643(8) 0.09488(10) 0.0833(5) Uani 1 1 d . . . . .
O5 O 0.74572(16) 0.71939(7) 0.28749(10) 0.0559(5) Uani 1 1 d . . . . .
O6 O 0.4106(2) 0.82368(9) 0.17549(12) 0.0779(6) Uani 1 1 d . . . . .
C38 C 0.6699(3) 0.81943(10) 0.21836(14) 0.0557(7) Uani 1 1 d . . . . .
H38 H 0.6494 0.8377 0.1665 0.067 Uiso 1 1 calc R U . . .
H39 H 0.7633 0.8054 0.2181 0.067 Uiso 1 1 calc R U . . .
C39 C 0.6601(2) 0.86379(10) 0.28239(14) 0.0463(6) Uani 1 1 d . . . . .
C40 C 0.6823(3) 0.92007(11) 0.26320(16) 0.0581(7) Uani 1 1 d . . . . .
H40 H 0.7018 0.9297 0.2103 0.070 Uiso 1 1 calc R U . . .
C41 C 0.6766(3) 0.96244(12) 0.3192(2) 0.0694(8) Uani 1 1 d . . . . .
H41 H 0.6909 1.0010 0.3047 0.083 Uiso 1 1 calc R U . . .
C42 C 0.6505(3) 0.94906(13) 0.39563(18) 0.0659(8) Uani 1 1 d . . . . .
H42 H 0.6474 0.9782 0.4345 0.079 Uiso 1 1 calc R U . . .
C43 C 0.6285(3) 0.89321(13) 0.41630(16) 0.0616(7) Uani 1 1 d . . . . .
H43 H 0.6107 0.8839 0.4695 0.074 Uiso 1 1 calc R U . . .
C44 C 0.6323(2) 0.85046(11) 0.35958(15) 0.0530(6) Uani 1 1 d . . . . .
H44 H 0.6157 0.8120 0.3739 0.064 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
C1 C6 1.377(3) . ?
C1 C2 1.388(3) . ?
C1 C7 1.506(3) . ?
C2 C3 1.373(3) . ?
C2 H1 0.9500 . ?
C3 C4 1.370(4) . ?
C3 H2 0.9500 . ?
C4 C5 1.368(4) . ?
C4 H3 0.9500 . ?
C5 C6 1.383(4) . ?
C5 H4 0.9500 . ?
C6 H5 0.9500 . ?
C7 C9 1.522(3) . ?
C7 C8 1.529(3) . ?
C7 H6 1.0000 . ?
C8 H7 0.9800 . ?
C8 H8 0.9800 . ?
C8 H9 0.9800 . ?
C9 O1 1.426(3) . ?
C9 C10 1.558(3) . ?
C9 H10 1.0000 . ?
O1 H11 0.8400 . ?
C10 C14 1.507(3) . ?
C10 C11 1.528(3) . ?
C10 H12 1.0000 . ?
C11 C15 1.493(3) . ?
C11 C12 1.522(3) . ?
C11 H13 1.0000 . ?
C12 C13 1.498(3) . ?
C12 H14 0.9900 . ?
C12 H15 0.9900 . ?
C13 O2 1.206(3) . ?
C13 N1 1.402(3) . ?
N1 C14 1.384(3) . ?
N1 C16 1.478(3) . ?
C14 O3 1.212(3) . ?
C15 F1 1.337(3) . ?
C15 F2 1.338(3) . ?
C15 F3 1.339(3) . ?
C16 C17 1.507(3) . ?
C16 H16 0.9900 . ?
C16 H17 0.9900 . ?
C17 C18 1.384(3) . ?
C17 C22 1.387(3) . ?
C18 C19 1.380(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.371(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.371(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.384(4) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 C24 1.383(4) . ?
C23 C28 1.386(3) . ?
C23 C29 1.505(4) . ?
C24 C25 1.384(4) . ?
C24 H23 0.9500 . ?
C25 C26 1.364(4) . ?
C25 H24 0.9500 . ?
C26 C27 1.360(5) . ?
C26 H25 0.9500 . ?
C27 C28 1.388(4) . ?
C27 H26 0.9500 . ?
C28 H27 0.9500 . ?
C29 C30 1.529(3) . ?
C29 C31 1.535(4) . ?
C29 H28 1.0000 . ?
C30 H29 0.9800 . ?
C30 H30 0.9800 . ?
C30 H31 0.9800 . ?
C31 O4 1.426(3) . ?
C31 C33 1.545(3) . ?
C31 H32 1.0000 . ?
O4 H33 0.8400 . ?
C32 C37 1.499(4) . ?
C32 C36 1.514(3) . ?
C32 C33 1.525(3) . ?
C32 H34 1.0000 . ?
C33 C34 1.499(3) . ?
C33 H35 1.0000 . ?
C34 O5 1.225(3) . ?
C34 N2 1.381(3) . ?
N2 C35 1.394(3) . ?
N2 C38 1.466(3) . ?
C35 O6 1.203(3) . ?
C35 C36 1.487(4) . ?
C36 H36 0.9900 . ?
C36 H37 0.9900 . ?
C37 F5 1.333(3) . ?
C37 F4 1.334(3) . ?
C37 F6 1.335(3) . ?
C38 C39 1.508(3) . ?
C38 H38 0.9900 . ?
C38 H39 0.9900 . ?
C39 C40 1.380(3) . ?
C39 C44 1.381(3) . ?
C40 C41 1.377(4) . ?
C40 H40 0.9500 . ?
C41 C42 1.364(4) . ?
C41 H41 0.9500 . ?
C42 C43 1.377(4) . ?
C42 H42 0.9500 . ?
C43 C44 1.390(4) . ?
C43 H43 0.9500 . ?
C44 H44 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 C1 C2 117.8(2) . . ?
C6 C1 C7 121.0(2) . . ?
C2 C1 C7 121.1(2) . . ?
C3 C2 C1 121.1(2) . . ?
C3 C2 H1 119.5 . . ?
C1 C2 H1 119.5 . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 H2 119.9 . . ?
C2 C3 H2 119.9 . . ?
C5 C4 C3 119.7(3) . . ?
C5 C4 H3 120.1 . . ?
C3 C4 H3 120.1 . . ?
C4 C5 C6 120.0(3) . . ?
C4 C5 H4 120.0 . . ?
C6 C5 H4 120.0 . . ?
C1 C6 C5 121.1(2) . . ?
C1 C6 H5 119.4 . . ?
C5 C6 H5 119.4 . . ?
C1 C7 C9 112.72(18) . . ?
C1 C7 C8 109.96(19) . . ?
C9 C7 C8 110.52(19) . . ?
C1 C7 H6 107.8 . . ?
C9 C7 H6 107.8 . . ?
C8 C7 H6 107.8 . . ?
C7 C8 H7 109.5 . . ?
C7 C8 H8 109.5 . . ?
H7 C8 H8 109.5 . . ?
C7 C8 H9 109.5 . . ?
H7 C8 H9 109.5 . . ?
H8 C8 H9 109.5 . . ?
O1 C9 C7 108.99(19) . . ?
O1 C9 C10 108.62(17) . . ?
C7 C9 C10 113.06(18) . . ?
O1 C9 H10 108.7 . . ?
C7 C9 H10 108.7 . . ?
C10 C9 H10 108.7 . . ?
C9 O1 H11 109.5 . . ?
C14 C10 C11 113.84(19) . . ?
C14 C10 C9 108.81(18) . . ?
C11 C10 C9 111.39(18) . . ?
C14 C10 H12 107.5 . . ?
C11 C10 H12 107.5 . . ?
C9 C10 H12 107.5 . . ?
C15 C11 C12 112.0(2) . . ?
C15 C11 C10 112.73(19) . . ?
C12 C11 C10 110.33(19) . . ?
C15 C11 H13 107.2 . . ?
C12 C11 H13 107.2 . . ?
C10 C11 H13 107.2 . . ?
C13 C12 C11 114.5(2) . . ?
C13 C12 H14 108.6 . . ?
C11 C12 H14 108.6 . . ?
C13 C12 H15 108.6 . . ?
C11 C12 H15 108.6 . . ?
H14 C12 H15 107.6 . . ?
O2 C13 N1 120.0(2) . . ?
O2 C13 C12 122.1(2) . . ?
N1 C13 C12 117.9(2) . . ?
C14 N1 C13 124.18(19) . . ?
C14 N1 C16 118.6(2) . . ?
C13 N1 C16 117.2(2) . . ?
O3 C14 N1 120.4(2) . . ?
O3 C14 C10 120.1(2) . . ?
N1 C14 C10 119.5(2) . . ?
F1 C15 F2 105.9(2) . . ?
F1 C15 F3 105.0(2) . . ?
F2 C15 F3 106.9(2) . . ?
F1 C15 C11 112.8(2) . . ?
F2 C15 C11 112.2(2) . . ?
F3 C15 C11 113.4(2) . . ?
N1 C16 C17 113.78(19) . . ?
N1 C16 H16 108.8 . . ?
C17 C16 H16 108.8 . . ?
N1 C16 H17 108.8 . . ?
C17 C16 H17 108.8 . . ?
H16 C16 H17 107.7 . . ?
C18 C17 C22 118.2(2) . . ?
C18 C17 C16 119.3(2) . . ?
C22 C17 C16 122.5(2) . . ?
C19 C18 C17 121.0(3) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C20 C19 C18 120.2(3) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 119.6(3) . . ?
C19 C20 H20 120.2 . . ?
C21 C20 H20 120.2 . . ?
C20 C21 C22 120.5(3) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C21 C22 C17 120.5(2) . . ?
C21 C22 H22 119.8 . . ?
C17 C22 H22 119.8 . . ?
C24 C23 C28 117.8(3) . . ?
C24 C23 C29 121.4(2) . . ?
C28 C23 C29 120.6(2) . . ?
C23 C24 C25 121.2(3) . . ?
C23 C24 H23 119.4 . . ?
C25 C24 H23 119.4 . . ?
C26 C25 C24 120.2(3) . . ?
C26 C25 H24 119.9 . . ?
C24 C25 H24 119.9 . . ?
C27 C26 C25 119.4(3) . . ?
C27 C26 H25 120.3 . . ?
C25 C26 H25 120.3 . . ?
C26 C27 C28 121.1(3) . . ?
C26 C27 H26 119.4 . . ?
C28 C27 H26 119.4 . . ?
C23 C28 C27 120.2(3) . . ?
C23 C28 H27 119.9 . . ?
C27 C28 H27 119.9 . . ?
C23 C29 C30 112.6(2) . . ?
C23 C29 C31 110.6(2) . . ?
C30 C29 C31 110.5(2) . . ?
C23 C29 H28 107.6 . . ?
C30 C29 H28 107.6 . . ?
C31 C29 H28 107.6 . . ?
C29 C30 H29 109.5 . . ?
C29 C30 H30 109.5 . . ?
H29 C30 H30 109.5 . . ?
C29 C30 H31 109.5 . . ?
H29 C30 H31 109.5 . . ?
H30 C30 H31 109.5 . . ?
O4 C31 C29 111.5(2) . . ?
O4 C31 C33 106.28(19) . . ?
C29 C31 C33 113.0(2) . . ?
O4 C31 H32 108.6 . . ?
C29 C31 H32 108.6 . . ?
C33 C31 H32 108.6 . . ?
C31 O4 H33 109.5 . . ?
C37 C32 C36 111.8(2) . . ?
C37 C32 C33 112.2(2) . . ?
C36 C32 C33 110.9(2) . . ?
C37 C32 H34 107.2 . . ?
C36 C32 H34 107.2 . . ?
C33 C32 H34 107.2 . . ?
C34 C33 C32 113.5(2) . . ?
C34 C33 C31 107.50(19) . . ?
C32 C33 C31 112.0(2) . . ?
C34 C33 H35 107.9 . . ?
C32 C33 H35 107.9 . . ?
C31 C33 H35 107.9 . . ?
O5 C34 N2 119.9(2) . . ?
O5 C34 C33 120.5(2) . . ?
N2 C34 C33 119.6(2) . . ?
C34 N2 C35 124.1(2) . . ?
C34 N2 C38 119.2(2) . . ?
C35 N2 C38 116.6(2) . . ?
O6 C35 N2 120.0(2) . . ?
O6 C35 C36 121.8(2) . . ?
N2 C35 C36 118.2(2) . . ?
C35 C36 C32 115.0(2) . . ?
C35 C36 H36 108.5 . . ?
C32 C36 H36 108.5 . . ?
C35 C36 H37 108.5 . . ?
C32 C36 H37 108.5 . . ?
H36 C36 H37 107.5 . . ?
F5 C37 F4 105.8(2) . . ?
F5 C37 F6 106.4(2) . . ?
F4 C37 F6 106.0(3) . . ?
F5 C37 C32 112.7(3) . . ?
F4 C37 C32 112.1(2) . . ?
F6 C37 C32 113.1(2) . . ?
N2 C38 C39 114.3(2) . . ?
N2 C38 H38 108.7 . . ?
C39 C38 H38 108.7 . . ?
N2 C38 H39 108.7 . . ?
C39 C38 H39 108.7 . . ?
H38 C38 H39 107.6 . . ?
C40 C39 C44 118.6(2) . . ?
C40 C39 C38 118.5(2) . . ?
C44 C39 C38 122.9(2) . . ?
C41 C40 C39 121.2(3) . . ?
C41 C40 H40 119.4 . . ?
C39 C40 H40 119.4 . . ?
C42 C41 C40 120.0(3) . . ?
C42 C41 H41 120.0 . . ?
C40 C41 H41 120.0 . . ?
C41 C42 C43 119.9(3) . . ?
C41 C42 H42 120.1 . . ?
C43 C42 H42 120.1 . . ?
C42 C43 C44 120.2(3) . . ?
C42 C43 H43 119.9 . . ?
C44 C43 H43 119.9 . . ?
C39 C44 C43 120.0(2) . . ?
C39 C44 H44 120.0 . . ?
C43 C44 H44 120.0 . . ?

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(4) . . . . ?
C7 C1 C2 C3 -177.2(2) . . . . ?
C1 C2 C3 C4 1.4(4) . . . . ?
C2 C3 C4 C5 -1.0(5) . . . . ?
C3 C4 C5 C6 -0.4(5) . . . . ?
C2 C1 C6 C5 -1.1(4) . . . . ?
C7 C1 C6 C5 175.8(3) . . . . ?
C4 C5 C6 C1 1.4(5) . . . . ?
C6 C1 C7 C9 131.4(2) . . . . ?
C2 C1 C7 C9 -51.9(3) . . . . ?
C6 C1 C7 C8 -104.8(3) . . . . ?
C2 C1 C7 C8 71.9(3) . . . . ?
C1 C7 C9 O1 -177.78(17) . . . . ?
C8 C7 C9 O1 58.7(2) . . . . ?
C1 C7 C9 C10 -56.9(2) . . . . ?
C8 C7 C9 C10 179.62(19) . . . . ?
O1 C9 C10 C14 29.4(2) . . . . ?
C7 C9 C10 C14 -91.7(2) . . . . ?
O1 C9 C10 C11 -96.9(2) . . . . ?
C7 C9 C10 C11 142.00(19) . . . . ?
C14 C10 C11 C15 79.6(2) . . . . ?
C9 C10 C11 C15 -156.93(19) . . . . ?
C14 C10 C11 C12 -46.4(3) . . . . ?
C9 C10 C11 C12 77.1(2) . . . . ?
C15 C11 C12 C13 -77.2(3) . . . . ?
C10 C11 C12 C13 49.2(3) . . . . ?
C11 C12 C13 O2 153.2(2) . . . . ?
C11 C12 C13 N1 -28.1(3) . . . . ?
O2 C13 N1 C14 -178.7(2) . . . . ?
C12 C13 N1 C14 2.6(3) . . . . ?
O2 C13 N1 C16 1.1(3) . . . . ?
C12 C13 N1 C16 -177.7(2) . . . . ?
C13 N1 C14 O3 -179.3(2) . . . . ?
C16 N1 C14 O3 0.9(3) . . . . ?
C13 N1 C14 C10 -0.2(3) . . . . ?
C16 N1 C14 C10 180.00(19) . . . . ?
C11 C10 C14 O3 -157.6(2) . . . . ?
C9 C10 C14 O3 77.5(3) . . . . ?
C11 C10 C14 N1 23.3(3) . . . . ?
C9 C10 C14 N1 -101.6(2) . . . . ?
C12 C11 C15 F1 179.11(19) . . . . ?
C10 C11 C15 F1 54.0(3) . . . . ?
C12 C11 C15 F2 -61.3(3) . . . . ?
C10 C11 C15 F2 173.55(19) . . . . ?
C12 C11 C15 F3 59.8(3) . . . . ?
C10 C11 C15 F3 -65.3(3) . . . . ?
C14 N1 C16 C17 -97.5(3) . . . . ?
C13 N1 C16 C17 82.7(3) . . . . ?
N1 C16 C17 C18 -147.7(2) . . . . ?
N1 C16 C17 C22 33.5(3) . . . . ?
C22 C17 C18 C19 -1.0(4) . . . . ?
C16 C17 C18 C19 -179.8(2) . . . . ?
C17 C18 C19 C20 0.3(4) . . . . ?
C18 C19 C20 C21 0.5(4) . . . . ?
C19 C20 C21 C22 -0.6(4) . . . . ?
C20 C21 C22 C17 -0.1(4) . . . . ?
C18 C17 C22 C21 0.9(4) . . . . ?
C16 C17 C22 C21 179.7(2) . . . . ?
C28 C23 C24 C25 1.5(4) . . . . ?
C29 C23 C24 C25 -175.3(2) . . . . ?
C23 C24 C25 C26 -1.0(4) . . . . ?
C24 C25 C26 C27 -0.7(5) . . . . ?
C25 C26 C27 C28 1.9(5) . . . . ?
C24 C23 C28 C27 -0.3(4) . . . . ?
C29 C23 C28 C27 176.6(2) . . . . ?
C26 C27 C28 C23 -1.4(5) . . . . ?
C24 C23 C29 C30 -132.9(3) . . . . ?
C28 C23 C29 C30 50.4(3) . . . . ?
C24 C23 C29 C31 103.0(3) . . . . ?
C28 C23 C29 C31 -73.7(3) . . . . ?
C23 C29 C31 O4 179.03(19) . . . . ?
C30 C29 C31 O4 53.7(3) . . . . ?
C23 C29 C31 C33 -61.3(3) . . . . ?
C30 C29 C31 C33 173.3(2) . . . . ?
C37 C32 C33 C34 80.0(3) . . . . ?
C36 C32 C33 C34 -45.8(3) . . . . ?
C37 C32 C33 C31 -158.0(2) . . . . ?
C36 C32 C33 C31 76.2(3) . . . . ?
O4 C31 C33 C34 39.6(3) . . . . ?
C29 C31 C33 C34 -83.0(2) . . . . ?
O4 C31 C33 C32 -85.8(2) . . . . ?
C29 C31 C33 C32 151.6(2) . . . . ?
C32 C33 C34 O5 -159.3(2) . . . . ?
C31 C33 C34 O5 76.2(3) . . . . ?
C32 C33 C34 N2 22.0(3) . . . . ?
C31 C33 C34 N2 -102.5(2) . . . . ?
O5 C34 N2 C35 -175.4(2) . . . . ?
C33 C34 N2 C35 3.4(3) . . . . ?
O5 C34 N2 C38 2.5(3) . . . . ?
C33 C34 N2 C38 -178.8(2) . . . . ?
C34 N2 C35 O6 175.8(2) . . . . ?
C38 N2 C35 O6 -2.1(3) . . . . ?
C34 N2 C35 C36 -2.7(3) . . . . ?
C38 N2 C35 C36 179.5(2) . . . . ?
O6 C35 C36 C32 157.7(3) . . . . ?
N2 C35 C36 C32 -23.8(4) . . . . ?
C37 C32 C36 C35 -78.8(3) . . . . ?
C33 C32 C36 C35 47.3(3) . . . . ?
C36 C32 C37 F5 -179.8(2) . . . . ?
C33 C32 C37 F5 54.8(3) . . . . ?
C36 C32 C37 F4 -60.5(3) . . . . ?
C33 C32 C37 F4 174.1(2) . . . . ?
C36 C32 C37 F6 59.3(3) . . . . ?
C33 C32 C37 F6 -66.0(3) . . . . ?
C34 N2 C38 C39 -97.5(3) . . . . ?
C35 N2 C38 C39 80.5(3) . . . . ?
N2 C38 C39 C40 -148.1(2) . . . . ?
N2 C38 C39 C44 33.1(3) . . . . ?
C44 C39 C40 C41 -0.2(4) . . . . ?
C38 C39 C40 C41 -179.1(2) . . . . ?
C39 C40 C41 C42 0.9(4) . . . . ?
C40 C41 C42 C43 -0.7(4) . . . . ?
C41 C42 C43 C44 -0.3(4) . . . . ?
C40 C39 C44 C43 -0.7(4) . . . . ?
C38 C39 C44 C43 178.1(2) . . . . ?
C42 C43 C44 C39 1.0(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H11 O5 0.84 1.95 2.778(2) 171.0 1_455
C29 H28 O5 1.00 2.54 3.212(3) 124.0 .
O4 H33 O3 0.84 1.89 2.712(2) 166.7 .
C36 H36 F3 0.99 2.57 3.375(3) 138.0 4_575

_refine_diff_density_max         0.196
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.040

####################################################################### 
# 
# 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_TY0210
_database_code_depnum_ccdc_archive 'CCDC 1854141'
_audit_update_record             
;
2018-07-06 deposited with the CCDC.
2018-08-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'(2R*,3R*,4R*)-N-benzyl-6-oxo-2-{(S*)-1-phenylethyl}-4-(trifluoromethyl)tetrahydro-2H-pyran-3- carboxamide'
_chemical_name_common            ?
_chemical_melting_point          445.9
_chemical_formula_moiety         'C22 H22 F3 N O3'
_chemical_formula_sum            'C22 H22 F3 N O3'
_chemical_formula_weight         405.40

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'
O O 0.0106 0.0060 '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'
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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   10.8871(6)
_cell_length_b                   9.3186(5)
_cell_length_c                   19.1257(11)
_cell_angle_alpha                90
_cell_angle_beta                 101.892(6)
_cell_angle_gamma                90
_cell_volume                     1898.71(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    7836
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      31.50

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   0.987
_exptl_transmission_factor_max   0.990
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.113
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_T_min  0.94643
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.933
_oxdiff_exptl_absorpt_empirical_full_max 1.187
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22079
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.904
_diffrn_reflns_theta_max         25.496
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3520
_reflns_number_gt                2940
_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       
;
Rigaku CrystalClear-SM Expert 2.1 b29
;
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXTL-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
Yadokari-XG 2014 (Wakita, Nemoto, et al., 2016)
;
_computing_publication_material  
;
Yadokari-XG 2014 (Wakita, Nemoto, et al., 2016)
;
_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)+(0.0322P)²+0.6484P] 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         3520
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0328
_refine_ls_wR_factor_ref         0.0802
_refine_ls_wR_factor_gt          0.0741
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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 0.67139(12) 0.23662(15) 0.21657(7) 0.0296(3) Uani 1 1 d . . . . .
C2 C 0.60915(13) 0.11948(17) 0.18149(8) 0.0355(3) Uani 1 1 d . . . . .
H1 H 0.5490 0.0699 0.2021 0.043 Uiso 1 1 calc R U . . .
C3 C 0.63325(15) 0.07349(19) 0.11684(9) 0.0440(4) Uani 1 1 d . . . . .
H2 H 0.5904 -0.0077 0.0936 0.053 Uiso 1 1 calc R U . . .
C4 C 0.71941(16) 0.1454(2) 0.08622(9) 0.0476(4) Uani 1 1 d . . . . .
H3 H 0.7357 0.1146 0.0417 0.057 Uiso 1 1 calc R U . . .
C5 C 0.78178(16) 0.26238(19) 0.12075(10) 0.0491(5) Uani 1 1 d . . . . .
H4 H 0.8412 0.3123 0.0998 0.059 Uiso 1 1 calc R U . . .
C6 C 0.75859(15) 0.30739(17) 0.18539(9) 0.0407(4) Uani 1 1 d . . . . .
H5 H 0.8027 0.3876 0.2089 0.049 Uiso 1 1 calc R U . . .
C7 C 0.64627(13) 0.28527(16) 0.28760(8) 0.0348(3) Uani 1 1 d . . . . .
H6 H 0.5899 0.2151 0.3039 0.042 Uiso 1 1 calc R U . . .
H7 H 0.7264 0.2861 0.3232 0.042 Uiso 1 1 calc R U . . .
N1 N 0.58937(10) 0.42740(13) 0.28511(6) 0.0309(3) Uani 1 1 d . . . . .
H22 H 0.6376 0.5026 0.2980 0.037 Uiso 1 1 calc R U . . .
C8 C 0.46528(12) 0.44606(14) 0.26368(7) 0.0247(3) Uani 1 1 d . . . . .
O1 O 0.39292(9) 0.34563(10) 0.24706(6) 0.0341(2) Uani 1 1 d . . . . .
C9 C 0.41973(12) 0.60108(14) 0.26278(7) 0.0236(3) Uani 1 1 d . . . . .
H8 H 0.4943 0.6645 0.2787 0.028 Uiso 1 1 calc R U . . .
C10 C 0.35047(12) 0.65152(14) 0.18884(7) 0.0258(3) Uani 1 1 d . . . . .
H9 H 0.3255 0.7535 0.1943 0.031 Uiso 1 1 calc R U . . .
C11 C 0.22961(12) 0.56692(15) 0.16378(7) 0.0279(3) Uani 1 1 d . . . . .
H10 H 0.1714 0.6262 0.1288 0.033 Uiso 1 1 calc R U . . .
H11 H 0.2495 0.4801 0.1384 0.033 Uiso 1 1 calc R U . . .
C12 C 0.16246(12) 0.52083(14) 0.22147(7) 0.0247(3) Uani 1 1 d . . . . .
O2 O 0.21415(8) 0.54142(10) 0.29060(5) 0.0254(2) Uani 1 1 d . . . . .
C13 C 0.32798(11) 0.62603(14) 0.31224(7) 0.0231(3) Uani 1 1 d . . . . .
H12 H 0.3028 0.7294 0.3077 0.028 Uiso 1 1 calc R U . . .
O3 O 0.06316(9) 0.45892(11) 0.20699(5) 0.0345(2) Uani 1 1 d . . . . .
C14 C 0.43184(14) 0.65088(17) 0.13436(8) 0.0349(3) Uani 1 1 d . . . . .
F1 F 0.53295(10) 0.73440(13) 0.15455(5) 0.0619(3) Uani 1 1 d . . . . .
F2 F 0.47509(9) 0.52158(11) 0.12221(5) 0.0491(3) Uani 1 1 d . . . . .
F3 F 0.37131(10) 0.69995(12) 0.07103(5) 0.0551(3) Uani 1 1 d . . . . .
C15 C 0.38212(12) 0.59767(14) 0.39168(7) 0.0263(3) Uani 1 1 d . . . . .
H13 H 0.4735 0.6216 0.4000 0.032 Uiso 1 1 calc R U . . .
C16 C 0.37338(16) 0.44098(16) 0.41416(8) 0.0376(4) Uani 1 1 d . . . . .
H14 H 0.4124 0.4305 0.4649 0.056 Uiso 1 1 calc R U . . .
H15 H 0.4172 0.3797 0.3855 0.056 Uiso 1 1 calc R U . . .
H16 H 0.2850 0.4124 0.4065 0.056 Uiso 1 1 calc R U . . .
C17 C 0.32531(13) 0.69661(14) 0.43950(7) 0.0271(3) Uani 1 1 d . . . . .
C18 C 0.39938(14) 0.79507(15) 0.48346(7) 0.0329(3) Uani 1 1 d . . . . .
H17 H 0.4861 0.8020 0.4825 0.040 Uiso 1 1 calc R U . . .
C19 C 0.34962(16) 0.88366(17) 0.52873(8) 0.0423(4) Uani 1 1 d . . . . .
H18 H 0.4022 0.9495 0.5590 0.051 Uiso 1 1 calc R U . . .
C20 C 0.22378(17) 0.87601(19) 0.52978(8) 0.0461(4) Uani 1 1 d . . . . .
H19 H 0.1891 0.9368 0.5606 0.055 Uiso 1 1 calc R U . . .
C21 C 0.14857(16) 0.7801(2) 0.48612(9) 0.0469(4) Uani 1 1 d . . . . .
H20 H 0.0616 0.7750 0.4866 0.056 Uiso 1 1 calc R U . . .
C22 C 0.19873(14) 0.69098(18) 0.44139(8) 0.0394(4) Uani 1 1 d . . . . .
H21 H 0.1457 0.6249 0.4115 0.047 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
C1 C2 1.383(2) . ?
C1 C6 1.387(2) . ?
C1 C7 1.510(2) . ?
C2 C3 1.384(2) . ?
C2 H1 0.9500 . ?
C3 C4 1.378(2) . ?
C3 H2 0.9500 . ?
C4 C5 1.379(3) . ?
C4 H3 0.9500 . ?
C5 C6 1.377(2) . ?
C5 H4 0.9500 . ?
C6 H5 0.9500 . ?
C7 N1 1.4588(18) . ?
C7 H6 0.9900 . ?
C7 H7 0.9900 . ?
N1 C8 1.3399(17) . ?
N1 H22 0.8800 . ?
C8 O1 1.2224(16) . ?
C8 C9 1.5262(18) . ?
C9 C13 1.5284(17) . ?
C9 C10 1.5329(18) . ?
C9 H8 1.0000 . ?
C10 C14 1.5003(19) . ?
C10 C11 1.5240(18) . ?
C10 H9 1.0000 . ?
C11 C12 1.5063(19) . ?
C11 H10 0.9900 . ?
C11 H11 0.9900 . ?
C12 O3 1.2061(16) . ?
C12 O2 1.3397(16) . ?
O2 C13 1.4551(15) . ?
C13 C15 1.5351(18) . ?
C13 H12 1.0000 . ?
C14 F2 1.3314(17) . ?
C14 F3 1.3347(17) . ?
C14 F1 1.3385(17) . ?
C15 C17 1.5173(18) . ?
C15 C16 1.5306(19) . ?
C15 H13 1.0000 . ?
C16 H14 0.9800 . ?
C16 H15 0.9800 . ?
C16 H16 0.9800 . ?
C17 C18 1.3854(19) . ?
C17 C22 1.387(2) . ?
C18 C19 1.385(2) . ?
C18 H17 0.9500 . ?
C19 C20 1.376(2) . ?
C19 H18 0.9500 . ?
C20 C21 1.373(2) . ?
C20 H19 0.9500 . ?
C21 C22 1.383(2) . ?
C21 H20 0.9500 . ?
C22 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
C2 C1 C6 118.48(14) . . ?
C2 C1 C7 120.79(13) . . ?
C6 C1 C7 120.72(14) . . ?
C1 C2 C3 120.90(14) . . ?
C1 C2 H1 119.5 . . ?
C3 C2 H1 119.5 . . ?
C4 C3 C2 120.02(16) . . ?
C4 C3 H2 120.0 . . ?
C2 C3 H2 120.0 . . ?
C3 C4 C5 119.48(16) . . ?
C3 C4 H3 120.3 . . ?
C5 C4 H3 120.3 . . ?
C6 C5 C4 120.50(15) . . ?
C6 C5 H4 119.8 . . ?
C4 C5 H4 119.8 . . ?
C5 C6 C1 120.61(16) . . ?
C5 C6 H5 119.7 . . ?
C1 C6 H5 119.7 . . ?
N1 C7 C1 113.44(12) . . ?
N1 C7 H6 108.9 . . ?
C1 C7 H6 108.9 . . ?
N1 C7 H7 108.9 . . ?
C1 C7 H7 108.9 . . ?
H6 C7 H7 107.7 . . ?
C8 N1 C7 121.50(12) . . ?
C8 N1 H22 119.3 . . ?
C7 N1 H22 119.3 . . ?
O1 C8 N1 122.37(12) . . ?
O1 C8 C9 122.09(11) . . ?
N1 C8 C9 115.54(11) . . ?
C8 C9 C13 112.91(10) . . ?
C8 C9 C10 113.42(11) . . ?
C13 C9 C10 105.32(10) . . ?
C8 C9 H8 108.3 . . ?
C13 C9 H8 108.3 . . ?
C10 C9 H8 108.3 . . ?
C14 C10 C11 112.00(11) . . ?
C14 C10 C9 113.01(11) . . ?
C11 C10 C9 111.12(11) . . ?
C14 C10 H9 106.8 . . ?
C11 C10 H9 106.8 . . ?
C9 C10 H9 106.8 . . ?
C12 C11 C10 115.79(11) . . ?
C12 C11 H10 108.3 . . ?
C10 C11 H10 108.3 . . ?
C12 C11 H11 108.3 . . ?
C10 C11 H11 108.3 . . ?
H10 C11 H11 107.4 . . ?
O3 C12 O2 118.01(12) . . ?
O3 C12 C11 121.03(12) . . ?
O2 C12 C11 120.89(11) . . ?
C12 O2 C13 121.22(10) . . ?
O2 C13 C9 111.62(10) . . ?
O2 C13 C15 108.60(10) . . ?
C9 C13 C15 114.82(10) . . ?
O2 C13 H12 107.1 . . ?
C9 C13 H12 107.1 . . ?
C15 C13 H12 107.1 . . ?
F2 C14 F3 106.13(12) . . ?
F2 C14 F1 106.09(12) . . ?
F3 C14 F1 106.59(12) . . ?
F2 C14 C10 113.92(12) . . ?
F3 C14 C10 112.16(12) . . ?
F1 C14 C10 111.44(12) . . ?
C17 C15 C16 110.71(11) . . ?
C17 C15 C13 111.77(11) . . ?
C16 C15 C13 114.13(11) . . ?
C17 C15 H13 106.6 . . ?
C16 C15 H13 106.6 . . ?
C13 C15 H13 106.6 . . ?
C15 C16 H14 109.5 . . ?
C15 C16 H15 109.5 . . ?
H14 C16 H15 109.5 . . ?
C15 C16 H16 109.5 . . ?
H14 C16 H16 109.5 . . ?
H15 C16 H16 109.5 . . ?
C18 C17 C22 117.80(13) . . ?
C18 C17 C15 120.64(12) . . ?
C22 C17 C15 121.56(13) . . ?
C19 C18 C17 121.36(14) . . ?
C19 C18 H17 119.3 . . ?
C17 C18 H17 119.3 . . ?
C20 C19 C18 119.80(15) . . ?
C20 C19 H18 120.1 . . ?
C18 C19 H18 120.1 . . ?
C21 C20 C19 119.72(15) . . ?
C21 C20 H19 120.1 . . ?
C19 C20 H19 120.1 . . ?
C20 C21 C22 120.34(15) . . ?
C20 C21 H20 119.8 . . ?
C22 C21 H20 119.8 . . ?
C21 C22 C17 120.97(15) . . ?
C21 C22 H21 119.5 . . ?
C17 C22 H21 119.5 . . ?

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 0.1(2) . . . . ?
C7 C1 C2 C3 -179.13(13) . . . . ?
C1 C2 C3 C4 -0.6(2) . . . . ?
C2 C3 C4 C5 0.5(2) . . . . ?
C3 C4 C5 C6 0.1(2) . . . . ?
C4 C5 C6 C1 -0.5(2) . . . . ?
C2 C1 C6 C5 0.4(2) . . . . ?
C7 C1 C6 C5 179.69(14) . . . . ?
C2 C1 C7 N1 -115.13(15) . . . . ?
C6 C1 C7 N1 65.64(17) . . . . ?
C1 C7 N1 C8 83.70(16) . . . . ?
C7 N1 C8 O1 2.1(2) . . . . ?
C7 N1 C8 C9 -179.07(12) . . . . ?
O1 C8 C9 C13 59.36(16) . . . . ?
N1 C8 C9 C13 -119.48(12) . . . . ?
O1 C8 C9 C10 -60.36(16) . . . . ?
N1 C8 C9 C10 120.80(12) . . . . ?
C8 C9 C10 C14 -62.63(15) . . . . ?
C13 C9 C10 C14 173.41(11) . . . . ?
C8 C9 C10 C11 64.25(14) . . . . ?
C13 C9 C10 C11 -59.70(13) . . . . ?
C14 C10 C11 C12 161.10(12) . . . . ?
C9 C10 C11 C12 33.66(16) . . . . ?
C10 C11 C12 O3 176.68(12) . . . . ?
C10 C11 C12 O2 -6.49(18) . . . . ?
O3 C12 O2 C13 -174.52(11) . . . . ?
C11 C12 O2 C13 8.56(17) . . . . ?
C12 O2 C13 C9 -37.79(15) . . . . ?
C12 O2 C13 C15 -165.37(10) . . . . ?
C8 C9 C13 O2 -62.35(13) . . . . ?
C10 C9 C13 O2 61.93(13) . . . . ?
C8 C9 C13 C15 61.80(14) . . . . ?
C10 C9 C13 C15 -173.91(10) . . . . ?
C11 C10 C14 F2 -64.76(16) . . . . ?
C9 C10 C14 F2 61.66(16) . . . . ?
C11 C10 C14 F3 55.83(16) . . . . ?
C9 C10 C14 F3 -177.75(12) . . . . ?
C11 C10 C14 F1 175.24(12) . . . . ?
C9 C10 C14 F1 -58.34(16) . . . . ?
O2 C13 C15 C17 -86.96(13) . . . . ?
C9 C13 C15 C17 147.31(11) . . . . ?
O2 C13 C15 C16 39.65(15) . . . . ?
C9 C13 C15 C16 -86.09(14) . . . . ?
C16 C15 C17 C18 115.24(14) . . . . ?
C13 C15 C17 C18 -116.33(14) . . . . ?
C16 C15 C17 C22 -64.10(17) . . . . ?
C13 C15 C17 C22 64.34(17) . . . . ?
C22 C17 C18 C19 1.0(2) . . . . ?
C15 C17 C18 C19 -178.37(13) . . . . ?
C17 C18 C19 C20 -0.9(2) . . . . ?
C18 C19 C20 C21 0.3(3) . . . . ?
C19 C20 C21 C22 0.3(3) . . . . ?
C20 C21 C22 C17 -0.2(3) . . . . ?
C18 C17 C22 C21 -0.5(2) . . . . ?
C15 C17 C22 C21 178.90(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C7 H7 F1 0.99 2.61 3.4718(17) 145.4 2_645
C13 H12 O1 1.00 2.43 3.1833(16) 131.9 2
C13 H12 O3 1.00 2.64 3.3679(16) 130.0 2
C7 H7 F1 0.99 2.61 3.4718(17) 145.4 2_645
C13 H12 O1 1.00 2.43 3.1833(16) 131.9 2

_refine_diff_density_max         0.211
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.032

