##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
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##############################################################################
                                             
data_global
_audit_creation_method     'from SHELXL97 CIF and IUCr SHELXL97-template'
_journal_date_recd_electronic     2003-06-30
_journal_date_accepted     2003-07-16
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2003
_journal_volume     59
_journal_issue      9
_journal_page_first     o1398
_journal_page_last     o1399
_journal_paper_category     EO
_publ_contact_author_name     'Dr. Liming Shao'
_publ_contact_author_address
;
    Drug Discovery
     Sepracor Inc.
     84 Waterford Drive
     Marlborough, MA 01752
     U.S.A.
;
_publ_contact_author_email     liming.shao@sepracor.com
_publ_contact_author_fax     '617 496 5618'
_publ_contact_author_phone     '617 495 0787'
_publ_section_title
;
(S)-N-(1-Phenethylpiperidin-1-ium-3-ylmethyl)-N-phenylpropionamide
trifluoroacetate
;
loop_
    _publ_author_name
    _publ_author_address
    'Liming Shao'
;
Drug Discovery
Sepracor Inc.
84 Waterford Drive
Marlborough
MA 01752
USA.
;
    'Gregory D. Cuny'
;
Drug Discovery
Sepracor Inc.
84 Waterford Drive
Marlborough
MA 01752
USA.
;
    'James R. Hauske'
;
Drug Discovery
Sepracor Inc.
84 Waterford Drive
Marlborough
MA 01752
USA.
;
    'Richard J. Staples'
;
Department of Chemistry and Chemical Biology
Harvard University
Cambridge
MA 02138
USA.
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(S)-N-(1-Phenethylpiperidin-1-ium-3-ylmethyl)-N-phenylpropionamide
trifluoroacetate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C23 H31 N2 O1 1+, C2 F3 O2 1-'
_chemical_formula_sum     'C25 H31 F3 N2 O3'
_chemical_formula_iupac     'C23 H31 N2 O1 1+, C2 F3 O2 1-'
_chemical_formula_weight     464.52
_chemical_melting_point     ?
_symmetry_cell_setting     Orthorhombic
_symmetry_space_group_name_H-M     'P 21 21 21'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    '-x, y+1/2, -z+1/2'
    'x+1/2, -y+1/2, -z'
_cell_length_a     10.1973(7)
_cell_length_b     10.8295(7)
_cell_length_c     21.9100(10)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     2419.6(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     648
_cell_measurement_theta_min     2.96
_cell_measurement_theta_max     28.7
_cell_measurement_temperature     213(2)
_exptl_crystal_description     needle
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.25
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.275
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     984
_exptl_absorpt_coefficient_mu     0.099
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
Data was collected using a Bruker SMART CCD (charge coupled device) based
diffractometer equipped with an LT-2 low-temperature apparatus operating at
213 K.  A suitable crystal was chosen and mounted on a glass fiber using
grease.
Data were measured using omega scans of 0.3° per frame for 30 s , such
that a hemisphere was collected. A total of 1271 frames were collected with
a
final resolution of 0.75 Å.  The first 50 frames  were recollected at the
end
of data collection to monitor for decay.  Cell parameters were retrieved
using
SMART software and refined using SAINT on all observed reflections.  Data
reduction was performed using the SAINT software which corrects for Lp and
decay.  Absorption corrections were applied using SADABS based on Blessing,
(1995).  The structures are solved by the direct method using the SHELX-90
program and refined by least squares method on F2 SHELXL-93, incorporated in
SHELXTL V5.1.
;
_diffrn_ambient_temperature     213(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'normal-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker CCD'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     8.3
_diffrn_reflns_number     15557
_diffrn_reflns_av_R_equivalents     0.0548
_diffrn_reflns_av_sigmaI/netI     0.0255
_diffrn_reflns_theta_min     1.86
_diffrn_reflns_theta_max     28.33
_diffrn_reflns_theta_full     28.33
_diffrn_measured_fraction_theta_max     0.980
_diffrn_measured_fraction_theta_full     0.980
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     13
_diffrn_reflns_limit_k_min     -14
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -28
_diffrn_reflns_limit_l_max     26
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     <1
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     3332
_reflns_number_gt     3113
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0501
_refine_ls_R_factor_gt     0.0469
_refine_ls_wR_factor_gt     0.1213
_refine_ls_wR_factor_ref     0.1248
_refine_ls_goodness_of_fit_ref     1.098
_refine_ls_restrained_S_all     1.098
_refine_ls_number_reflns     3332
_refine_ls_number_parameters     321
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0653P)²+0.52P] where P = (Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.401
_refine_diff_density_min     -0.363
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     ?
_refine_ls_abs_structure_Flack     ?
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'
_computing_data_collection     'SMART (Bruker, 1998)'
_computing_cell_refinement     SMART
_computing_data_reduction     'SAINT (Bruker, 1999)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1990)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL (Bruker, 1998)'
_computing_publication_material     SHELXL97
loop_
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    _atom_site_type_symbol
    C1 0.77365(19) 0.6452(2) 0.25998(9) 0.0335(4) Uani d . 1 . . C
    H1A 0.8599 0.6417 0.2404 0.040 Uiso calc R 1 . . H
    H1B 0.7441 0.5604 0.2675 0.040 Uiso calc R 1 . . H
    O1 0.97375(17) 0.42215(18) 0.32919(8) 0.0510(4) Uani d . 1 . . O
    N1 0.67772(16) 0.71023(16) 0.21882(7) 0.0311(3) Uani d . 1 . . N
    H1 0.602(3) 0.704(2) 0.2403(11) 0.029(6) Uiso d . 1 . . H
    N2 0.81872(16) 0.52443(16) 0.38306(8) 0.0334(4) Uani d . 1 . . N
    C2 0.78372(19) 0.71502(19) 0.32052(9) 0.0322(4) Uani d . 1 . . C
    H2A 0.6947 0.7199 0.3384 0.039 Uiso calc R 1 . . H
    C3 0.8317(2) 0.8468(2) 0.30927(11) 0.0436(5) Uani d . 1 . . C
    H3A 0.8347 0.8919 0.3480 0.052 Uiso calc R 1 . . H
    H3B 0.9206 0.8447 0.2923 0.052 Uiso calc R 1 . . H
    C4 0.7400(3) 0.9130(2) 0.26492(11) 0.0449(5) Uani d . 1 . . C
    H4A 0.6546 0.9253 0.2845 0.054 Uiso calc R 1 . . H
    H4B 0.7762 0.9946 0.2553 0.054 Uiso calc R 1 . . H
    C5 0.7211(2) 0.8410(2) 0.20607(10) 0.0411(5) Uani d . 1 . . C
    H5A 0.6551 0.8824 0.1808 0.049 Uiso calc R 1 . . H
    H5B 0.8037 0.8396 0.1832 0.049 Uiso calc R 1 . . H
    C6 0.6530(2) 0.6370(2) 0.16163(9) 0.0395(5) Uani d . 1 . . C
    H6A 0.6490 0.5490 0.1717 0.047 Uiso calc R 1 . . H
    H6B 0.7257 0.6495 0.1331 0.047 Uiso calc R 1 . . H
    C7 0.5250(3) 0.6761(3) 0.13135(13) 0.0581(7) Uani d . 1 . . C
    H7A 0.4559 0.6789 0.1624 0.070 Uiso calc R 1 . . H
    H7B 0.5355 0.7597 0.1150 0.070 Uiso calc R 1 . . H
    C8 0.4811(2) 0.5912(2) 0.08004(10) 0.0419(5) Uani d . 1 . . C
    C9 0.4668(3) 0.4647(3) 0.08934(11) 0.0493(6) Uani d . 1 . . C
    H9A 0.4886 0.4305 0.1275 0.059 Uiso calc R 1 . . H
    C10 0.4211(3) 0.3888(3) 0.04330(15) 0.0631(8) Uani d . 1 . . C
    H10A 0.4127 0.3035 0.0503 0.076 Uiso calc R 1 . . H
    C11 0.3881(3) 0.4365(4) -0.01218(14) 0.0652(9) Uani d . 1 . . C
    H11A 0.3565 0.3845 -0.0433 0.078 Uiso calc R 1 . . H
    C12 0.4016(3) 0.5629(4) -0.02249(11) 0.0626(8) Uani d . 1 . . C
    H12A 0.3790 0.5962 -0.0607 0.075 Uiso calc R 1 . . H
    C13 0.4479(2) 0.6395(3) 0.02312(11) 0.0516(6) Uani d . 1 . . C
    H13A 0.4570 0.7246 0.0157 0.062 Uiso calc R 1 . . H
    C14 0.8715(2) 0.6460(2) 0.36570(10) 0.0372(4) Uani d . 1 . . C
    H14A 0.9584 0.6348 0.3474 0.045 Uiso calc R 1 . . H
    H14B 0.8821 0.6963 0.4025 0.045 Uiso calc R 1 . . H
    C15 0.8777(2) 0.4190(2) 0.36282(10) 0.0367(4) Uani d . 1 . . C
    C16 0.8188(2) 0.2982(2) 0.38471(13) 0.0468(5) Uani d . 1 . . C
    H16A 0.8115 0.3006 0.4293 0.056 Uiso calc R 1 . . H
    H16B 0.7301 0.2903 0.3680 0.056 Uiso calc R 1 . . H
    C17 0.8974(4) 0.1863(3) 0.3667(2) 0.0798(11) Uani d . 1 . . C
    H17A 0.8546 0.1125 0.3819 0.120 Uiso calc R 1 . . H
    H17B 0.9848 0.1922 0.3839 0.120 Uiso calc R 1 . . H
    H17C 0.9034 0.1821 0.3225 0.120 Uiso calc R 1 . . H
    C18 0.70467(19) 0.52458(19) 0.42202(9) 0.0320(4) Uani d . 1 . . C
    C19 0.7195(2) 0.5384(3) 0.48496(10) 0.0453(5) Uani d . 1 . . C
    H19A 0.8037 0.5449 0.5021 0.054 Uiso calc R 1 . . H
    C20 0.6095(3) 0.5426(3) 0.52228(11) 0.0543(7) Uani d . 1 . . C
    H20A 0.6194 0.5510 0.5647 0.065 Uiso calc R 1 . . H
    C21 0.4846(3) 0.5345(3) 0.49701(11) 0.0503(6) Uani d . 1 . . C
    H21A 0.4102 0.5380 0.5223 0.060 Uiso calc R 1 . . H
    C22 0.4704(2) 0.5214(2) 0.43472(11) 0.0427(5) Uani d . 1 . . C
    H22A 0.3860 0.5161 0.4177 0.051 Uiso calc R 1 . . H
    C23 0.5796(2) 0.5161(2) 0.39692(9) 0.0353(4) Uani d . 1 . . C
    H23A 0.5690 0.5068 0.3545 0.042 Uiso calc R 1 . . H
    C24 0.6211(2) 0.2773(2) 0.22002(10) 0.0358(4) Uani d . 1 A . C
    C25 0.7464(3) 0.2675(3) 0.18029(14) 0.0545(7) Uani d . 1 . . C
    O2 0.6075(2) 0.37242(18) 0.24934(10) 0.0580(5) Uani d . 1 . . O
    O3 0.54885(17) 0.18503(18) 0.21666(9) 0.0510(4) Uani d . 1 . . O
    F1A 0.8041(6) 0.1650(5) 0.1804(4) 0.124(4) Uani d P 0.652(10) A 1 F
    F2A 0.7053(5) 0.2798(5) 0.11853(14) 0.0872(14) Uani d P 0.652(10) A 1 F
    F3A 0.8201(2) 0.3675(2) 0.17958(13) 0.0973(8) Uani d . 1 A 1 F
    F1B 0.8463(5) 0.2175(9) 0.2244(4) 0.083(3) Uani d P 0.348(10) A 2 F
    F2B 0.7531(9) 0.1915(18) 0.1416(7) 0.153(9) Uani d P 0.348(10) A 2 F
_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_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 N1 . 1.505(2) ?
    C1 C2 . 1.530(3) ?
    C1 H1A . 0.9800 ?
    C1 H1B . 0.9800 ?
    O1 C15 . 1.226(3) ?
    N1 C6 . 1.504(3) ?
    N1 C5 . 1.510(3) ?
    N1 H1 . 0.91(3) ?
    N2 C15 . 1.364(3) ?
    N2 C18 . 1.443(2) ?
    N2 C14 . 1.472(3) ?
    C2 C3 . 1.529(3) ?
    C2 C14 . 1.530(3) ?
    C2 H2A . 0.9900 ?
    C3 C4 . 1.528(3) ?
    C3 H3A . 0.9800 ?
    C3 H3B . 0.9800 ?
    C4 C5 . 1.519(3) ?
    C4 H4A . 0.9800 ?
    C4 H4B . 0.9800 ?
    C5 H5A . 0.9800 ?
    C5 H5B . 0.9800 ?
    C6 C7 . 1.524(3) ?
    C6 H6A . 0.9800 ?
    C6 H6B . 0.9800 ?
    C7 C8 . 1.520(3) ?
    C7 H7A . 0.9800 ?
    C7 H7B . 0.9800 ?
    C8 C9 . 1.393(4) ?
    C8 C13 . 1.394(3) ?
    C9 C10 . 1.382(4) ?
    C9 H9A . 0.9400 ?
    C10 C11 . 1.363(5) ?
    C10 H10A . 0.9400 ?
    C11 C12 . 1.395(5) ?
    C11 H11A . 0.9400 ?
    C12 C13 . 1.382(4) ?
    C12 H12A . 0.9400 ?
    C13 H13A . 0.9400 ?
    C14 H14A . 0.9800 ?
    C14 H14B . 0.9800 ?
    C15 C16 . 1.517(3) ?
    C16 C17 . 1.506(4) ?
    C16 H16A . 0.9800 ?
    C16 H16B . 0.9800 ?
    C17 H17A . 0.9700 ?
    C17 H17B . 0.9700 ?
    C17 H17C . 0.9700 ?
    C18 C23 . 1.392(3) ?
    C18 C19 . 1.395(3) ?
    C19 C20 . 1.389(4) ?
    C19 H19A . 0.9400 ?
    C20 C21 . 1.391(4) ?
    C20 H20A . 0.9400 ?
    C21 C22 . 1.380(3) ?
    C21 H21A . 0.9400 ?
    C22 C23 . 1.389(3) ?
    C22 H22A . 0.9400 ?
    C23 H23A . 0.9400 ?
    C24 O2 . 1.222(3) ?
    C24 O3 . 1.244(3) ?
    C24 C25 . 1.550(3) ?
    C25 F2B . 1.184(8) ?
    C25 F1A . 1.256(4) ?
    C25 F3A . 1.318(3) ?
    C25 F2A . 1.423(5) ?
    C25 F1B . 1.506(7) ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    N1 C1 C2 . . 109.37(16) ?
    N1 C1 H1A . . 109.8 ?
    C2 C1 H1A . . 109.8 ?
    N1 C1 H1B . . 109.8 ?
    C2 C1 H1B . . 109.8 ?
    H1A C1 H1B . . 108.2 ?
    C6 N1 C1 . . 111.20(16) ?
    C6 N1 C5 . . 112.91(16) ?
    C1 N1 C5 . . 111.06(16) ?
    C6 N1 H1 . . 104.6(15) ?
    C1 N1 H1 . . 101.8(15) ?
    C5 N1 H1 . . 114.6(16) ?
    C15 N2 C18 . . 123.27(17) ?
    C15 N2 C14 . . 120.20(17) ?
    C18 N2 C14 . . 116.53(17) ?
    C3 C2 C14 . . 111.92(17) ?
    C3 C2 C1 . . 110.06(17) ?
    C14 C2 C1 . . 111.01(17) ?
    C3 C2 H2A . . 107.9 ?
    C14 C2 H2A . . 107.9 ?
    C1 C2 H2A . . 107.9 ?
    C4 C3 C2 . . 110.17(19) ?
    C4 C3 H3A . . 109.6 ?
    C2 C3 H3A . . 109.6 ?
    C4 C3 H3B . . 109.6 ?
    C2 C3 H3B . . 109.6 ?
    H3A C3 H3B . . 108.1 ?
    C5 C4 C3 . . 112.1(2) ?
    C5 C4 H4A . . 109.2 ?
    C3 C4 H4A . . 109.2 ?
    C5 C4 H4B . . 109.2 ?
    C3 C4 H4B . . 109.2 ?
    H4A C4 H4B . . 107.9 ?
    N1 C5 C4 . . 111.21(17) ?
    N1 C5 H5A . . 109.4 ?
    C4 C5 H5A . . 109.4 ?
    N1 C5 H5B . . 109.4 ?
    C4 C5 H5B . . 109.4 ?
    H5A C5 H5B . . 108.0 ?
    N1 C6 C7 . . 111.12(18) ?
    N1 C6 H6A . . 109.4 ?
    C7 C6 H6A . . 109.4 ?
    N1 C6 H6B . . 109.4 ?
    C7 C6 H6B . . 109.4 ?
    H6A C6 H6B . . 108.0 ?
    C8 C7 C6 . . 114.0(2) ?
    C8 C7 H7A . . 108.8 ?
    C6 C7 H7A . . 108.8 ?
    C8 C7 H7B . . 108.8 ?
    C6 C7 H7B . . 108.8 ?
    H7A C7 H7B . . 107.7 ?
    C9 C8 C13 . . 118.3(2) ?
    C9 C8 C7 . . 121.2(2) ?
    C13 C8 C7 . . 120.4(2) ?
    C10 C9 C8 . . 120.9(3) ?
    C10 C9 H9A . . 119.6 ?
    C8 C9 H9A . . 119.6 ?
    C11 C10 C9 . . 120.6(3) ?
    C11 C10 H10A . . 119.7 ?
    C9 C10 H10A . . 119.7 ?
    C10 C11 C12 . . 119.5(3) ?
    C10 C11 H11A . . 120.3 ?
    C12 C11 H11A . . 120.3 ?
    C13 C12 C11 . . 120.4(3) ?
    C13 C12 H12A . . 119.8 ?
    C11 C12 H12A . . 119.8 ?
    C12 C13 C8 . . 120.3(3) ?
    C12 C13 H13A . . 119.8 ?
    C8 C13 H13A . . 119.8 ?
    N2 C14 C2 . . 112.98(16) ?
    N2 C14 H14A . . 109.0 ?
    C2 C14 H14A . . 109.0 ?
    N2 C14 H14B . . 109.0 ?
    C2 C14 H14B . . 109.0 ?
    H14A C14 H14B . . 107.8 ?
    O1 C15 N2 . . 121.6(2) ?
    O1 C15 C16 . . 122.0(2) ?
    N2 C15 C16 . . 116.37(18) ?
    C17 C16 C15 . . 113.6(2) ?
    C17 C16 H16A . . 108.8 ?
    C15 C16 H16A . . 108.8 ?
    C17 C16 H16B . . 108.8 ?
    C15 C16 H16B . . 108.8 ?
    H16A C16 H16B . . 107.7 ?
    C16 C17 H17A . . 109.5 ?
    C16 C17 H17B . . 109.5 ?
    H17A C17 H17B . . 109.5 ?
    C16 C17 H17C . . 109.5 ?
    H17A C17 H17C . . 109.5 ?
    H17B C17 H17C . . 109.5 ?
    C23 C18 C19 . . 119.77(19) ?
    C23 C18 N2 . . 120.32(17) ?
    C19 C18 N2 . . 119.86(18) ?
    C20 C19 C18 . . 119.9(2) ?
    C20 C19 H19A . . 120.1 ?
    C18 C19 H19A . . 120.1 ?
    C19 C20 C21 . . 120.2(2) ?
    C19 C20 H20A . . 119.9 ?
    C21 C20 H20A . . 119.9 ?
    C22 C21 C20 . . 119.7(2) ?
    C22 C21 H21A . . 120.1 ?
    C20 C21 H21A . . 120.1 ?
    C21 C22 C23 . . 120.7(2) ?
    C21 C22 H22A . . 119.7 ?
    C23 C22 H22A . . 119.7 ?
    C22 C23 C18 . . 119.75(18) ?
    C22 C23 H23A . . 120.1 ?
    C18 C23 H23A . . 120.1 ?
    O2 C24 O3 . . 129.9(2) ?
    O2 C24 C25 . . 116.5(2) ?
    O3 C24 C25 . . 113.6(2) ?
    F2B C25 F1A . . 50.2(8) ?
    F2B C25 F3A . . 122.0(7) ?
    F1A C25 F3A . . 117.3(4) ?
    F2B C25 F2A . . 53.2(11) ?
    F1A C25 F2A . . 102.8(5) ?
    F3A C25 F2A . . 94.6(3) ?
    F2B C25 F1B . . 99.8(9) ?
    F1A C25 F1B . . 50.5(4) ?
    F3A C25 F1B . . 85.3(4) ?
    F2A C25 F1B . . 147.6(4) ?
    F2B C25 C24 . . 119.8(5) ?
    F1A C25 C24 . . 116.5(3) ?
    F3A C25 C24 . . 114.9(2) ?
    F2A C25 C24 . . 106.6(3) ?
    F1B C25 C24 . . 102.8(3) ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C2 C1 N1 C6 . . . . -173.50(16) ?
    C2 C1 N1 C5 . . . . 59.9(2) ?
    N1 C1 C2 C3 . . . . -60.3(2) ?
    N1 C1 C2 C14 . . . . 175.23(16) ?
    C14 C2 C3 C4 . . . . -178.9(2) ?
    C1 C2 C3 C4 . . . . 57.1(2) ?
    C2 C3 C4 C5 . . . . -53.9(3) ?
    C6 N1 C5 C4 . . . . 177.84(19) ?
    C1 N1 C5 C4 . . . . -56.5(2) ?
    C3 C4 C5 N1 . . . . 53.4(3) ?
    C1 N1 C6 C7 . . . . 159.9(2) ?
    C5 N1 C6 C7 . . . . -74.5(2) ?
    N1 C6 C7 C8 . . . . -169.6(2) ?
    C6 C7 C8 C9 . . . . 54.2(4) ?
    C6 C7 C8 C13 . . . . -129.0(3) ?
    C13 C8 C9 C10 . . . . 0.2(4) ?
    C7 C8 C9 C10 . . . . 177.0(3) ?
    C8 C9 C10 C11 . . . . -0.5(4) ?
    C9 C10 C11 C12 . . . . 0.4(4) ?
    C10 C11 C12 C13 . . . . -0.1(5) ?
    C11 C12 C13 C8 . . . . -0.3(4) ?
    C9 C8 C13 C12 . . . . 0.2(4) ?
    C7 C8 C13 C12 . . . . -176.6(3) ?
    C15 N2 C14 C2 . . . . 109.1(2) ?
    C18 N2 C14 C2 . . . . -71.3(2) ?
    C3 C2 C14 N2 . . . . 173.01(18) ?
    C1 C2 C14 N2 . . . . -63.6(2) ?
    C18 N2 C15 O1 . . . . 179.20(19) ?
    C14 N2 C15 O1 . . . . -1.3(3) ?
    C18 N2 C15 C16 . . . . -1.4(3) ?
    C14 N2 C15 C16 . . . . 178.2(2) ?
    O1 C15 C16 C17 . . . . 6.0(4) ?
    N2 C15 C16 C17 . . . . -173.4(3) ?
    C15 N2 C18 C23 . . . . -85.5(3) ?
    C14 N2 C18 C23 . . . . 94.9(2) ?
    C15 N2 C18 C19 . . . . 97.2(3) ?
    C14 N2 C18 C19 . . . . -82.4(3) ?
    C23 C18 C19 C20 . . . . 0.6(4) ?
    N2 C18 C19 C20 . . . . 177.9(2) ?
    C18 C19 C20 C21 . . . . -0.8(4) ?
    C19 C20 C21 C22 . . . . 0.4(5) ?
    C20 C21 C22 C23 . . . . 0.1(4) ?
    C21 C22 C23 C18 . . . . -0.3(4) ?
    C19 C18 C23 C22 . . . . 0.0(3) ?
    N2 C18 C23 C22 . . . . -177.4(2) ?
    O2 C24 C25 F2B . . . . -164.3(14) ?
    O3 C24 C25 F2B . . . . 15.5(14) ?
    O2 C24 C25 F1A . . . . 138.3(6) ?
    O3 C24 C25 F1A . . . . -41.9(7) ?
    O2 C24 C25 F3A . . . . -4.4(4) ?
    O3 C24 C25 F3A . . . . 175.4(3) ?
    O2 C24 C25 F2A . . . . -107.7(3) ?
    O3 C24 C25 F2A . . . . 72.1(3) ?
    O2 C24 C25 F1B . . . . 86.3(5) ?
    O3 C24 C25 F1B . . . . -93.9(5) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    N1 H1 O3 3_655 0.91(3) 1.82(3) 2.722(2) 178(2)
