#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/92/2229270.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2229270
loop_
_publ_author_name
'Wang, En-Ju'
'Chen, Guang-Ying'
_publ_section_title
;
 rac-4-[4-Cyano-2-(hydroxymethyl)phenyl]-4-(4-fluorophenyl)-4-hydroxy-N,N-dimethylbutanaminium
 hemifumarate
;
_journal_coeditor_code           XU5099
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o284
_journal_paper_doi               10.1107/S1600536810054346
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C20 H24 F N2 O2 +, 0.5C4 H2 O4 2-'
_chemical_formula_moiety         'C20 H24 F N2 O2 +, 0.5(C4 H2 O4 2-)'
_chemical_formula_sum            'C22 H25 F N2 O4'
_chemical_formula_weight         400.44
_chemical_name_systematic
;
rac-4-[4-Cyano-2-(hydroxymethyl)phenyl]-4-(4-fluorophenyl)-4-hydroxy-
N,N-dimethylbutanaminium hemifumarate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                92.2360(10)
_cell_angle_beta                 102.681(2)
_cell_angle_gamma                107.508(2)
_cell_formula_units_Z            2
_cell_length_a                   8.3312(9)
_cell_length_b                   8.8372(11)
_cell_length_c                   15.0396(13)
_cell_measurement_reflns_used    5256
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.2
_cell_measurement_theta_min      1.5
_cell_volume                     1023.64(19)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0156
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7766
_diffrn_reflns_theta_full        27.10
_diffrn_reflns_theta_max         27.10
_diffrn_reflns_theta_min         1.40
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.47
_refine_diff_density_max         0.802
_refine_diff_density_min         -0.291
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         4381
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0540
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0681P)²+0.4116P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1386
_refine_ls_wR_factor_ref         0.1575
_reflns_number_gt                3071
_reflns_number_total             4381
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            xu5099.cif
_cod_data_source_block           I
_cod_database_code               2229270
_cod_database_fobs_code          2229270
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_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
F F1 0.20769(19) 0.79749(15) 0.86453(10) 0.0671(4) Uani d . 1 . .
N N1 -0.2494(2) -0.04111(19) 0.61890(12) 0.0480(4) Uani d . 1 . .
H H1A -0.2346 0.0452 0.5868 0.058 Uiso calc R 1 A 1
N N2 1.1468(3) 0.2082(3) 1.02194(19) 0.0865(8) Uani d . 1 . .
O O1 0.38654(19) 0.25106(19) 0.66277(9) 0.0536(4) Uani d . 1 . .
H H1 0.4688 0.3252 0.6562 0.080 Uiso calc R 1 . .
O O2 0.6756(2) 0.4911(2) 0.67399(11) 0.0690(5) Uani d . 1 . .
H H2 0.7266 0.4358 0.6545 0.104 Uiso calc R 1 . .
O O3 0.7715(2) 0.2781(2) 0.58894(13) 0.0765(5) Uani d . 1 . .
O O4 0.8536(3) 0.1944(2) 0.47374(15) 0.0906(6) Uani d . 1 . .
C C1 0.5496(2) 0.2512(2) 0.81662(12) 0.0382(4) Uani d . 1 . .
C C2 0.5520(3) 0.1242(2) 0.86801(13) 0.0450(4) Uani d . 1 . .
H H2A 0.4472 0.0468 0.8671 0.054 Uiso calc R 1 . .
C C3 0.7026(3) 0.1076(2) 0.92031(14) 0.0479(5) Uani d . 1 . .
H H3 0.6992 0.0202 0.9532 0.057 Uiso calc R 1 . .
C C4 0.8584(3) 0.2230(3) 0.92298(14) 0.0482(5) Uani d . 1 . .
C C5 0.8597(3) 0.3513(3) 0.87273(15) 0.0505(5) Uani d . 1 . .
H H5 0.9654 0.4280 0.8745 0.061 Uiso calc R 1 . .
C C6 0.7095(2) 0.3695(2) 0.82005(13) 0.0445(4) Uani d . 1 . .
C C7 0.3417(2) 0.4110(2) 0.78555(12) 0.0374(4) Uani d . 1 . .
C C8 0.3553(2) 0.4536(2) 0.87729(13) 0.0414(4) Uani d . 1 . .
H H8 0.3930 0.3925 0.9212 0.050 Uiso calc R 1 . .
C C9 0.3138(3) 0.5849(2) 0.90451(14) 0.0460(5) Uani d . 1 . .
H H9 0.3241 0.6138 0.9661 0.055 Uiso calc R 1 . .
C C10 0.2568(3) 0.6718(2) 0.83815(15) 0.0470(5) Uani d . 1 . .
C C11 0.2425(3) 0.6358(2) 0.74730(15) 0.0510(5) Uani d . 1 . .
H H11 0.2047 0.6978 0.7040 0.061 Uiso calc R 1 . .
C C12 0.2858(3) 0.5040(2) 0.72121(14) 0.0477(5) Uani d . 1 . .
H H12 0.2773 0.4775 0.6595 0.057 Uiso calc R 1 . .
C C13 0.3780(2) 0.2592(2) 0.75605(12) 0.0405(4) Uani d . 1 . .
C C14 0.2230(2) 0.1135(2) 0.75868(15) 0.0481(5) Uani d . 1 C .
H H14A 0.2482 0.0170 0.7430 0.058 Uiso calc R 1 . .
H H14B 0.2064 0.1117 0.8205 0.058 Uiso calc R 1 . .
C C15 0.0558(3) 0.1151(3) 0.69250(17) 0.0589(6) Uani d . 1 . .
H H15A 0.0034 0.1812 0.7216 0.071 Uiso calc R 1 B 1
H H15B 0.0834 0.1619 0.6383 0.071 Uiso calc R 1 B 1
C C16 -0.0679(8) -0.0449(7) 0.6654(7) 0.0476(17) Uani d P 0.466(14) C 1
H H16A -0.0737 -0.1014 0.7192 0.057 Uiso calc PR 0.466(14) C 1
H H16B -0.0279 -0.1029 0.6235 0.057 Uiso calc PR 0.466(14) C 1
C C17 -0.3573(14) -0.0310(15) 0.6699(7) 0.081(3) Uani d P 0.466(14) C 1
H H17A -0.4580 -0.0138 0.6323 0.121 Uiso calc PR 0.466(14) C 1
H H17B -0.3005 0.0565 0.7174 0.121 Uiso calc PR 0.466(14) C 1
H H17C -0.3919 -0.1285 0.6971 0.121 Uiso calc PR 0.466(14) C 1
C C18 -0.3287(14) -0.1936(14) 0.5463(7) 0.072(2) Uani d P 0.466(14) C 1
H H18A -0.3457 -0.2878 0.5774 0.109 Uiso calc PR 0.466(14) C 1
H H18B -0.2506 -0.1931 0.5078 0.109 Uiso calc PR 0.466(14) C 1
H H18C -0.4380 -0.1927 0.5093 0.109 Uiso calc PR 0.466(14) C 1
C C16' -0.1003(8) -0.0176(9) 0.7010(5) 0.0522(17) Uani d P 0.534(14) C 2
H H16C -0.1343 0.0073 0.7560 0.063 Uiso calc PR 0.534(14) C 2
H H16D -0.0713 -0.1157 0.7065 0.063 Uiso calc PR 0.534(14) C 2
C C17' -0.4188(10) -0.0984(12) 0.6542(6) 0.0696(19) Uani d P 0.534(14) C 2
H H17D -0.5174 -0.1059 0.6051 0.104 Uiso calc PR 0.534(14) C 2
H H17E -0.4126 -0.0232 0.7037 0.104 Uiso calc PR 0.534(14) C 2
H H17F -0.4304 -0.2012 0.6755 0.104 Uiso calc PR 0.534(14) C 2
C C18' -0.2597(14) -0.1404(10) 0.5439(6) 0.069(2) Uani d P 0.534(14) C 2
H H18D -0.2704 -0.2459 0.5609 0.104 Uiso calc PR 0.534(14) C 2
H H18E -0.1566 -0.1009 0.5219 0.104 Uiso calc PR 0.534(14) C 2
H H18F -0.3592 -0.1438 0.4964 0.104 Uiso calc PR 0.534(14) C 2
C C19 1.0189(3) 0.2131(3) 0.97840(17) 0.0611(6) Uani d . 1 . .
C C20 0.7315(3) 0.5186(3) 0.77151(16) 0.0566(6) Uani d . 1 . .
H H20A 0.6673 0.5809 0.7936 0.068 Uiso calc R 1 . .
H H20B 0.8532 0.5823 0.7882 0.068 Uiso calc R 1 . .
C C21 0.8499(3) 0.3012(3) 0.52575(16) 0.0546(5) Uani d . 1 . .
C C22 0.9421(3) 0.4749(3) 0.52195(16) 0.0596(6) Uani d . 1 . .
H H22 0.9121 0.5504 0.5538 0.072 Uiso calc R 1 . .
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'
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
C17 N1 C18' . . 134.8(5) ?
C17 N1 C16' . . 93.0(5) ?
C18' N1 C16' . . 117.9(5) ?
C17 N1 C16 . . 119.4(5) ?
C18' N1 C16 . . 92.2(4) ?
C16' N1 C16 . . 27.2(2) ?
C17 N1 C17' . . 24.3(4) ?
C18' N1 C17' . . 110.8(4) ?
C16' N1 C17' . . 106.5(4) ?
C16 N1 C17' . . 128.0(5) ?
C17 N1 C18 . . 111.7(5) ?
C18' N1 C18 . . 23.5(4) ?
C16' N1 C18 . . 124.9(6) ?
C16 N1 C18 . . 104.7(5) ?
C17' N1 C18 . . 87.5(4) ?
C17 N1 H1A . . 106.8 ?
C18' N1 H1A . . 92.0 ?
C16' N1 H1A . . 111.9 ?
C16 N1 H1A . . 106.8 ?
C17' N1 H1A . . 117.7 ?
C18 N1 H1A . . 106.8 ?
C13 O1 H1 . . 109.5 ?
C20 O2 H2 . . 109.5 ?
C2 C1 C6 . . 117.88(17) ?
C2 C1 C13 . . 120.62(16) ?
C6 C1 C13 . . 121.48(16) ?
C3 C2 C1 . . 123.02(18) ?
C3 C2 H2A . . 118.5 ?
C1 C2 H2A . . 118.5 ?
C2 C3 C4 . . 118.84(19) ?
C2 C3 H3 . . 120.6 ?
C4 C3 H3 . . 120.6 ?
C3 C4 C5 . . 119.35(18) ?
C3 C4 C19 . . 120.94(19) ?
C5 C4 C19 . . 119.7(2) ?
C6 C5 C4 . . 122.44(19) ?
C6 C5 H5 . . 118.8 ?
C4 C5 H5 . . 118.8 ?
C5 C6 C1 . . 118.47(18) ?
C5 C6 C20 . . 116.23(18) ?
C1 C6 C20 . . 125.30(18) ?
C12 C7 C8 . . 118.55(17) ?
C12 C7 C13 . . 121.01(16) ?
C8 C7 C13 . . 120.36(16) ?
C9 C8 C7 . . 121.12(17) ?
C9 C8 H8 . . 119.4 ?
C7 C8 H8 . . 119.4 ?
C10 C9 C8 . . 118.15(18) ?
C10 C9 H9 . . 120.9 ?
C8 C9 H9 . . 120.9 ?
C11 C10 F1 . . 118.72(18) ?
C11 C10 C9 . . 123.02(19) ?
F1 C10 C9 . . 118.24(19) ?
C10 C11 C12 . . 118.06(18) ?
C10 C11 H11 . . 121.0 ?
C12 C11 H11 . . 121.0 ?
C11 C12 C7 . . 121.10(18) ?
C11 C12 H12 . . 119.5 ?
C7 C12 H12 . . 119.5 ?
O1 C13 C7 . . 111.63(15) ?
O1 C13 C14 . . 103.90(15) ?
C7 C13 C14 . . 109.04(15) ?
O1 C13 C1 . . 109.05(15) ?
C7 C13 C1 . . 110.65(14) ?
C14 C13 C1 . . 112.41(15) ?
C15 C14 C13 . . 112.24(17) ?
C15 C14 H14A . . 109.2 ?
C13 C14 H14A . . 109.2 ?
C15 C14 H14B . . 109.2 ?
C13 C14 H14B . . 109.2 ?
H14A C14 H14B . . 107.9 ?
C16 C15 C16' . . 27.9(2) ?
C16 C15 C14 . . 111.9(3) ?
C16' C15 C14 . . 112.9(3) ?
C16 C15 H15A . . 109.2 ?
C16' C15 H15A . . 83.4 ?
C14 C15 H15A . . 109.2 ?
C16 C15 H15B . . 109.2 ?
C16' C15 H15B . . 129.4 ?
C14 C15 H15B . . 109.2 ?
H15A C15 H15B . . 107.9 ?
C15 C16 N1 . . 111.9(4) ?
C15 C16 H16A . . 109.2 ?
N1 C16 H16A . . 109.2 ?
C15 C16 H16B . . 109.2 ?
N1 C16 H16B . . 109.2 ?
H16A C16 H16B . . 107.9 ?
N1 C17 H17A . . 109.5 ?
N1 C17 H17B . . 109.5 ?
N1 C17 H17C . . 109.5 ?
N1 C18 H18A . . 109.5 ?
N1 C18 H18B . . 109.5 ?
N1 C18 H18C . . 109.5 ?
C15 C16' N1 . . 111.1(4) ?
C15 C16' H16C . . 109.4 ?
N1 C16' H16C . . 109.4 ?
C15 C16' H16D . . 109.4 ?
N1 C16' H16D . . 109.4 ?
H16C C16' H16D . . 108.0 ?
N1 C17' H17D . . 109.5 ?
N1 C17' H17E . . 109.5 ?
H17D C17' H17E . . 109.5 ?
N1 C17' H17F . . 109.5 ?
H17D C17' H17F . . 109.5 ?
H17E C17' H17F . . 109.5 ?
N1 C18' H18D . . 109.5 ?
N1 C18' H18E . . 109.5 ?
H18D C18' H18E . . 109.5 ?
N1 C18' H18F . . 109.5 ?
H18D C18' H18F . . 109.5 ?
H18E C18' H18F . . 109.5 ?
N2 C19 C4 . . 178.8(3) ?
O2 C20 C6 . . 115.10(19) ?
O2 C20 H20A . . 108.5 ?
C6 C20 H20A . . 108.5 ?
O2 C20 H20B . . 108.5 ?
C6 C20 H20B . . 108.5 ?
H20A C20 H20B . . 107.5 ?
O4 C21 O3 . . 123.6(2) ?
O4 C21 C22 . . 123.2(2) ?
O3 C21 C22 . . 113.2(2) ?
C22 C22 C21 2_766 . 124.2(3) ?
C22 C22 H22 2_766 . 117.9 ?
C21 C22 H22 . . 117.9 ?
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
F1 C10 . 1.367(2) ?
N1 C17 . 1.323(9) ?
N1 C18' . 1.373(8) ?
N1 C16' . 1.504(5) ?
N1 C16 . 1.531(6) ?
N1 C17' . 1.566(8) ?
N1 C18 . 1.574(10) ?
N1 H1A . 0.9100 ?
N2 C19 . 1.136(3) ?
O1 C13 . 1.420(2) ?
O1 H1 . 0.8200 ?
O2 C20 . 1.425(3) ?
O2 H2 . 0.8200 ?
O3 C21 . 1.257(3) ?
O4 C21 . 1.214(3) ?
C1 C2 . 1.391(3) ?
C1 C6 . 1.414(3) ?
C1 C13 . 1.540(2) ?
C2 C3 . 1.378(3) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.380(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.386(3) ?
C4 C19 . 1.441(3) ?
C5 C6 . 1.384(3) ?
C5 H5 . 0.9300 ?
C6 C20 . 1.514(3) ?
C7 C12 . 1.386(3) ?
C7 C8 . 1.387(3) ?
C7 C13 . 1.531(3) ?
C8 C9 . 1.379(3) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.372(3) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.362(3) ?
C11 C12 . 1.386(3) ?
C11 H11 . 0.9300 ?
C12 H12 . 0.9300 ?
C13 C14 . 1.534(3) ?
C14 C15 . 1.528(3) ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C15 C16 . 1.456(6) ?
C15 C16' . 1.500(6) ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 0.9600 ?
C16' H16C . 0.9700 ?
C16' H16D . 0.9700 ?
C17' H17D . 0.9600 ?
C17' H17E . 0.9600 ?
C17' H17F . 0.9600 ?
C18' H18D . 0.9600 ?
C18' H18E . 0.9600 ?
C18' H18F . 0.9600 ?
C20 H20A . 0.9700 ?
C20 H20B . 0.9700 ?
C21 C22 . 1.506(3) ?
C22 C22 2_766 1.269(4) ?
C22 H22 . 0.9300 ?
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
O1 H1 O2 . 0.82 1.85 2.655(2) 165
O2 H2 O3 . 0.82 1.85 2.642(3) 162
N1 H1A O4 1_455 0.91 2.30 3.152(3) 155
N1 H1A O3 1_455 0.91 2.04 2.834(3) 145
C2 H2A F1 1_545 0.93 2.48 3.392(3) 167
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
C6 C1 C2 C3 . . . . -1.1(3) ?
C13 C1 C2 C3 . . . . 177.22(18) ?
C1 C2 C3 C4 . . . . 0.8(3) ?
C2 C3 C4 C5 . . . . -0.5(3) ?
C2 C3 C4 C19 . . . . 178.5(2) ?
C3 C4 C5 C6 . . . . 0.6(3) ?
C19 C4 C5 C6 . . . . -178.4(2) ?
C4 C5 C6 C1 . . . . -0.9(3) ?
C4 C5 C6 C20 . . . . 178.1(2) ?
C2 C1 C6 C5 . . . . 1.2(3) ?
C13 C1 C6 C5 . . . . -177.17(17) ?
C2 C1 C6 C20 . . . . -177.78(19) ?
C13 C1 C6 C20 . . . . 3.9(3) ?
C12 C7 C8 C9 . . . . 0.3(3) ?
C13 C7 C8 C9 . . . . -176.38(17) ?
C7 C8 C9 C10 . . . . 0.7(3) ?
C8 C9 C10 C11 . . . . -1.2(3) ?
C8 C9 C10 F1 . . . . 176.93(17) ?
F1 C10 C11 C12 . . . . -177.34(18) ?
C9 C10 C11 C12 . . . . 0.8(3) ?
C10 C11 C12 C7 . . . . 0.2(3) ?
C8 C7 C12 C11 . . . . -0.7(3) ?
C13 C7 C12 C11 . . . . 175.92(18) ?
C12 C7 C13 O1 . . . . 13.5(2) ?
C8 C7 C13 O1 . . . . -169.91(16) ?
C12 C7 C13 C14 . . . . -100.7(2) ?
C8 C7 C13 C14 . . . . 75.9(2) ?
C12 C7 C13 C1 . . . . 135.18(18) ?
C8 C7 C13 C1 . . . . -48.3(2) ?
C2 C1 C13 O1 . . . . -116.40(18) ?
C6 C1 C13 O1 . . . . 61.9(2) ?
C2 C1 C13 C7 . . . . 120.45(18) ?
C6 C1 C13 C7 . . . . -61.3(2) ?
C2 C1 C13 C14 . . . . -1.7(2) ?
C6 C1 C13 C14 . . . . 176.56(17) ?
O1 C13 C14 C15 . . . . -57.5(2) ?
C7 C13 C14 C15 . . . . 61.7(2) ?
C1 C13 C14 C15 . . . . -175.25(17) ?
C13 C14 C15 C16 . . . . 155.5(5) ?
C13 C14 C15 C16' . . . . -174.2(5) ?
C16' C15 C16 N1 . . . . 68.1(7) ?
C14 C15 C16 N1 . . . . 166.0(5) ?
C17 N1 C16 C15 . . . . -86.9(12) ?
C18' N1 C16 C15 . . . . 126.9(9) ?
C16' N1 C16 C15 . . . . -71.4(7) ?
C17' N1 C16 C15 . . . . -114.3(9) ?
C18 N1 C16 C15 . . . . 147.1(9) ?
C16 C15 C16' N1 . . . . -69.9(7) ?
C14 C15 C16' N1 . . . . -163.8(5) ?
C17 N1 C16' C15 . . . . -127.4(10) ?
C18' N1 C16' C15 . . . . 86.9(9) ?
C16 N1 C16' C15 . . . . 66.2(7) ?
C17' N1 C16' C15 . . . . -147.9(8) ?
C18 N1 C16' C15 . . . . 113.4(9) ?
C3 C4 C19 N2 . . . . -164(14) ?
C5 C4 C19 N2 . . . . 15(14) ?
C5 C6 C20 O2 . . . . 119.3(2) ?
C1 C6 C20 O2 . . . . -61.7(3) ?
O4 C21 C22 C22 . . . 2_766 -14.6(4) ?
O3 C21 C22 C22 . . . 2_766 164.3(3) ?
