#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/94/2229454.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_2229454
loop_
_publ_author_name
'Karpoormath, Rajshekhar'
'Govender, Patrick'
'Govender, Thavendran'
'Kruger, Hendrik G.'
'Maguire, Glenn E. M.'
_publ_section_title
;
 endo-11-(Dibenzylamino)tetracyclo[5.4.0.0^3,10^.0^5,9^]undecane-8-one
;
_journal_coeditor_code           LX2177
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o619
_journal_paper_doi               10.1107/S160053681100479X
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C25 H21 N O'
_chemical_formula_moiety         'C25 H21 N O'
_chemical_formula_sum            'C25 H21 N O'
_chemical_formula_weight         351.43
_chemical_name_systematic
;
endo-11-(Dibenzylamino)tetracyclo[5.4.0.0^3,10^.0^5,9^]undecane-8-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.100(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.6117(3)
_cell_length_b                   16.4344(7)
_cell_length_c                   17.2331(8)
_cell_measurement_reflns_used    3299
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      69.22
_cell_measurement_theta_min      5.17
_cell_volume                     1858.18(14)
_computing_cell_refinement       'SAINT (Bruker, 2006)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2006)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'Bruker Kappa DUO APEXII'
_diffrn_measurement_method       '1.2° φ scans and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_av_sigmaI/netI    0.0094
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            24662
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         69.22
_diffrn_reflns_theta_min         3.73
_exptl_absorpt_coefficient_mu    0.589
_exptl_absorpt_correction_T_max  0.8666
_exptl_absorpt_correction_T_min  0.7857
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2006)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.480
_refine_diff_density_min         -0.462
_refine_ls_extinction_coef       0.0020(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3303
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0660
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0800P)²+1.9830P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1723
_refine_ls_wR_factor_ref         0.1728
_reflns_number_gt                3240
_reflns_number_total             3303
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lx2177.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2229454
_cod_database_fobs_code          2229454
loop_
_symmetry_equiv_pos_as_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'
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
O O1 0.1742(2) 0.13889(10) 0.19402(10) 0.0394(4) Uani d . 1 . .
N N1 -0.2672(3) 0.05165(10) 0.14408(10) 0.0271(4) Uani d . 1 . .
C C2 -0.4175(5) 0.27147(16) 0.1215(3) 0.0763(12) Uani d DU 1 . .
C C3 -0.3558(3) 0.19546(14) 0.17218(17) 0.0423(6) Uani d . 1 . .
H H3 -0.4438 0.1857 0.2145 0.051 Uiso calc R 1 . .
C C4 -0.3624(3) 0.12730(13) 0.11264(14) 0.0347(5) Uani d . 1 . .
H H4 -0.5077 0.1160 0.0920 0.042 Uiso calc R 1 . .
C C5 -0.2577(4) 0.16781(17) 0.04842(17) 0.0493(7) Uani d . 1 . .
H H5 -0.2759 0.1387 -0.0029 0.059 Uiso calc R 1 . .
C C6 -0.3393(6) 0.25559(17) 0.04539(18) 0.0652(10) Uani d DU 1 . .
C C7 -0.1306(5) 0.30438(16) 0.16140(19) 0.0612(9) Uani d DU 1 . .
C C8 -0.1293(3) 0.22060(14) 0.20361(17) 0.0422(6) Uani d . 1 . .
H H8 -0.0991 0.2233 0.2619 0.051 Uiso calc R 1 . .
C C9 0.0227(3) 0.17342(14) 0.16393(15) 0.0361(5) Uani d . 1 . .
C C10 -0.0309(4) 0.19225(18) 0.07827(17) 0.0497(7) Uani d . 1 . .
H H10 0.0730 0.1760 0.0437 0.060 Uiso calc R 1 . .
C C11 -0.0792(5) 0.2836(2) 0.0801(2) 0.0775(12) Uani d DU 1 . .
C C12 -0.3867(3) 0.01601(13) 0.20230(13) 0.0311(5) Uani d . 1 . .
H H12A -0.3795 -0.0440 0.1982 0.037 Uiso calc R 1 . .
H H12B -0.5311 0.0318 0.1884 0.037 Uiso calc R 1 . .
C C13 -0.3230(3) 0.03943(13) 0.28639(13) 0.0307(5) Uani d . 1 . .
C C14 -0.4688(4) 0.04214(14) 0.33779(14) 0.0372(5) Uani d . 1 . .
H H14 -0.6085 0.0347 0.3185 0.045 Uiso calc R 1 . .
C C15 -0.4127(4) 0.05563(15) 0.41683(15) 0.0436(6) Uani d . 1 . .
H H15 -0.5139 0.0568 0.4514 0.052 Uiso calc R 1 . .
C C16 -0.2108(4) 0.06739(16) 0.44562(15) 0.0467(6) Uani d . 1 . .
H H16 -0.1722 0.0761 0.4999 0.056 Uiso calc R 1 . .
C C17 -0.0654(4) 0.06631(17) 0.39452(15) 0.0452(6) Uani d . 1 . .
H H17 0.0736 0.0755 0.4138 0.054 Uiso calc R 1 . .
C C18 -0.1200(4) 0.05196(15) 0.31545(14) 0.0384(6) Uani d . 1 . .
H H18 -0.0184 0.0507 0.2810 0.046 Uiso calc R 1 . .
C C19 -0.2474(4) -0.00746(14) 0.08166(13) 0.0349(5) Uani d . 1 . .
H H19A -0.1791 0.0190 0.0403 0.042 Uiso calc R 1 . .
H H19B -0.3851 -0.0244 0.0580 0.042 Uiso calc R 1 . .
C C20 -0.1277(3) -0.08185(13) 0.11058(12) 0.0312(5) Uani d . 1 . .
C C21 0.0737(3) -0.07388(14) 0.14401(14) 0.0381(5) Uani d . 1 . .
H H21 0.1342 -0.0214 0.1496 0.046 Uiso calc R 1 . .
C C22 0.1864(4) -0.14184(16) 0.16920(16) 0.0434(6) Uani d . 1 . .
H H22 0.3238 -0.1357 0.1921 0.052 Uiso calc R 1 . .
C C23 0.1013(4) -0.21862(15) 0.16137(15) 0.0416(6) Uani d . 1 . .
H H23 0.1796 -0.2652 0.1785 0.050 Uiso calc R 1 . .
C C24 -0.0992(4) -0.22698(15) 0.12834(15) 0.0413(6) Uani d . 1 . .
H H24 -0.1593 -0.2795 0.1228 0.050 Uiso calc R 1 . .
C C25 -0.2121(4) -0.15900(14) 0.10333(14) 0.0363(5) Uani d . 1 . .
H H25 -0.3498 -0.1653 0.0808 0.044 Uiso calc R 1 . .
C C1A -0.3205(6) 0.3417(2) 0.1498(2) 0.0414(11) Uani d PDU 0.621(7) . .
H H1A -0.3673 0.3612 0.1989 0.050 Uiso calc PR 0.621(7) . .
H H1B -0.3281 0.3860 0.1106 0.050 Uiso calc PR 0.621(7) . .
C C1B -0.2299(8) 0.3246(3) 0.0321(4) 0.0458(19) Uani d PDU 0.379(7) . .
H H1D -0.2791 0.3753 0.0546 0.055 Uiso calc PR 0.379(7) . .
H H1C -0.2020 0.3321 -0.0225 0.055 Uiso calc PR 0.379(7) . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C4 N1 C19 . . 111.32(17) ?
C4 N1 C12 . . 110.30(16) ?
C19 N1 C12 . . 109.88(17) ?
C1A C2 C6 . . 105.1(3) ?
C1A C2 C3 . . 113.4(3) ?
C6 C2 C3 . . 105.0(2) ?
C4 C3 C2 . . 103.3(2) ?
C4 C3 C8 . . 111.81(19) ?
C2 C3 C8 . . 98.9(2) ?
C4 C3 H3 . . 113.8 ?
C2 C3 H3 . . 113.8 ?
C8 C3 H3 . . 113.8 ?
N1 C4 C3 . . 113.65(19) ?
N1 C4 C5 . . 115.1(2) ?
C3 C4 C5 . . 101.0(2) ?
N1 C4 H4 . . 108.9 ?
C3 C4 H4 . . 108.9 ?
C5 C4 H4 . . 108.9 ?
C4 C5 C6 . . 104.2(2) ?
C4 C5 C10 . . 111.9(2) ?
C6 C5 C10 . . 95.0(2) ?
C4 C5 H5 . . 114.6 ?
C6 C5 H5 . . 114.6 ?
C10 C5 H5 . . 114.6 ?
C1B C6 C2 . . 104.3(4) ?
C1B C6 C5 . . 126.0(4) ?
C2 C6 C5 . . 107.0(2) ?
C1A C7 C11 . . 105.5(3) ?
C1A C7 C8 . . 114.2(3) ?
C11 C7 C8 . . 104.1(2) ?
C9 C8 C7 . . 102.1(2) ?
C9 C8 C3 . . 111.6(2) ?
C7 C8 C3 . . 96.9(2) ?
C9 C8 H8 . . 114.7 ?
C7 C8 H8 . . 114.7 ?
C3 C8 H8 . . 114.7 ?
O1 C9 C8 . . 127.8(2) ?
O1 C9 C10 . . 126.7(2) ?
C8 C9 C10 . . 104.5(2) ?
C9 C10 C11 . . 101.8(3) ?
C9 C10 C5 . . 111.5(2) ?
C11 C10 C5 . . 93.7(2) ?
C9 C10 H10 . . 115.7 ?
C11 C10 H10 . . 115.7 ?
C5 C10 H10 . . 115.7 ?
C1B C11 C7 . . 102.3(4) ?
C1B C11 C10 . . 126.7(4) ?
C7 C11 C10 . . 108.0(2) ?
N1 C12 C13 . . 116.31(17) ?
N1 C12 H12A . . 108.2 ?
C13 C12 H12A . . 108.2 ?
N1 C12 H12B . . 108.2 ?
C13 C12 H12B . . 108.2 ?
H12A C12 H12B . . 107.4 ?
C18 C13 C14 . . 118.8(2) ?
C18 C13 C12 . . 121.8(2) ?
C14 C13 C12 . . 119.2(2) ?
C15 C14 C13 . . 120.7(2) ?
C15 C14 H14 . . 119.7 ?
C13 C14 H14 . . 119.7 ?
C16 C15 C14 . . 120.4(2) ?
C16 C15 H15 . . 119.8 ?
C14 C15 H15 . . 119.8 ?
C15 C16 C17 . . 119.2(2) ?
C15 C16 H16 . . 120.4 ?
C17 C16 H16 . . 120.4 ?
C16 C17 C18 . . 120.8(2) ?
C16 C17 H17 . . 119.6 ?
C18 C17 H17 . . 119.6 ?
C17 C18 C13 . . 120.2(2) ?
C17 C18 H18 . . 119.9 ?
C13 C18 H18 . . 119.9 ?
N1 C19 C20 . . 112.67(17) ?
N1 C19 H19A . . 109.1 ?
C20 C19 H19A . . 109.1 ?
N1 C19 H19B . . 109.1 ?
C20 C19 H19B . . 109.1 ?
H19A C19 H19B . . 107.8 ?
C25 C20 C21 . . 118.6(2) ?
C25 C20 C19 . . 121.6(2) ?
C21 C20 C19 . . 119.8(2) ?
C22 C21 C20 . . 120.4(2) ?
C22 C21 H21 . . 119.8 ?
C20 C21 H21 . . 119.8 ?
C23 C22 C21 . . 120.6(2) ?
C23 C22 H22 . . 119.7 ?
C21 C22 H22 . . 119.7 ?
C22 C23 C24 . . 119.3(2) ?
C22 C23 H23 . . 120.4 ?
C24 C23 H23 . . 120.4 ?
C25 C24 C23 . . 120.1(2) ?
C25 C24 H24 . . 120.0 ?
C23 C24 H24 . . 120.0 ?
C24 C25 C20 . . 121.0(2) ?
C24 C25 H25 . . 119.5 ?
C20 C25 H25 . . 119.5 ?
C2 C1A C7 . . 93.1(3) ?
C2 C1A H1A . . 113.1 ?
C7 C1A H1A . . 113.1 ?
C2 C1A H1B . . 113.1 ?
C7 C1A H1B . . 113.1 ?
H1A C1A H1B . . 110.5 ?
C6 C1B C11 . . 81.7(3) ?
C6 C1B H1D . . 115.0 ?
C11 C1B H1D . . 115.0 ?
C6 C1B H1C . . 115.0 ?
C11 C1B H1C . . 115.0 ?
H1D C1B H1C . . 112.1 ?
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
O1 C9 . 1.211(3) ?
N1 C4 . 1.467(3) ?
N1 C19 . 1.467(3) ?
N1 C12 . 1.473(3) ?
C2 C1A . 1.380(4) ?
C2 C6 . 1.491(5) ?
C2 C3 . 1.550(4) ?
C3 C4 . 1.516(3) ?
C3 C8 . 1.583(3) ?
C3 H3 . 1.0000 ?
C4 C5 . 1.529(3) ?
C4 H4 . 1.0000 ?
C5 C6 . 1.539(4) ?
C5 C10 . 1.576(4) ?
C5 H5 . 1.0000 ?
C6 C1B . 1.379(4) ?
C7 C1A . 1.389(4) ?
C7 C11 . 1.522(5) ?
C7 C8 . 1.557(4) ?
C8 C9 . 1.500(3) ?
C8 H8 . 1.0000 ?
C9 C10 . 1.507(4) ?
C10 C11 . 1.536(4) ?
C10 H10 . 1.0000 ?
C11 C1B . 1.387(4) ?
C12 C13 . 1.508(3) ?
C12 H12A . 0.9900 ?
C12 H12B . 0.9900 ?
C13 C18 . 1.388(3) ?
C13 C14 . 1.388(3) ?
C14 C15 . 1.385(4) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.379(4) ?
C15 H15 . 0.9500 ?
C16 C17 . 1.382(4) ?
C16 H16 . 0.9500 ?
C17 C18 . 1.386(4) ?
C17 H17 . 0.9500 ?
C18 H18 . 0.9500 ?
C19 C20 . 1.507(3) ?
C19 H19A . 0.9900 ?
C19 H19B . 0.9900 ?
C20 C25 . 1.385(3) ?
C20 C21 . 1.390(3) ?
C21 C22 . 1.383(3) ?
C21 H21 . 0.9500 ?
C22 C23 . 1.381(4) ?
C22 H22 . 0.9500 ?
C23 C24 . 1.383(4) ?
C23 H23 . 0.9500 ?
C24 C25 . 1.383(3) ?
C24 H24 . 0.9500 ?
C25 H25 . 0.9500 ?
C1A H1A . 0.9900 ?
C1A H1B . 0.9900 ?
C1B H1D . 0.9900 ?
C1B H1C . 0.9900 ?
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
C1A C2 C3 C4 . . . . -145.8(3) ?
C6 C2 C3 C4 . . . . -31.6(3) ?
C1A C2 C3 C8 . . . . -30.7(3) ?
C6 C2 C3 C8 . . . . 83.4(3) ?
C19 N1 C4 C3 . . . . -170.57(19) ?
C12 N1 C4 C3 . . . . 67.2(2) ?
C19 N1 C4 C5 . . . . -54.8(3) ?
C12 N1 C4 C5 . . . . -177.03(19) ?
C2 C3 C4 N1 . . . . 167.47(19) ?
C8 C3 C4 N1 . . . . 62.0(3) ?
C2 C3 C4 C5 . . . . 43.6(2) ?
C8 C3 C4 C5 . . . . -61.8(2) ?
N1 C4 C5 C6 . . . . -162.24(19) ?
C3 C4 C5 C6 . . . . -39.4(2) ?
N1 C4 C5 C10 . . . . -60.8(3) ?
C3 C4 C5 C10 . . . . 62.1(3) ?
C1A C2 C6 C1B . . . . -8.8(3) ?
C3 C2 C6 C1B . . . . -128.7(3) ?
C1A C2 C6 C5 . . . . 126.6(3) ?
C3 C2 C6 C5 . . . . 6.7(3) ?
C4 C5 C6 C1B . . . . 143.1(4) ?
C10 C5 C6 C1B . . . . 29.1(5) ?
C4 C5 C6 C2 . . . . 20.3(3) ?
C10 C5 C6 C2 . . . . -93.7(3) ?
C1A C7 C8 C9 . . . . 144.0(3) ?
C11 C7 C8 C9 . . . . 29.5(3) ?
C1A C7 C8 C3 . . . . 30.1(3) ?
C11 C7 C8 C3 . . . . -84.4(2) ?
C4 C3 C8 C9 . . . . 2.7(3) ?
C2 C3 C8 C9 . . . . -105.6(3) ?
C4 C3 C8 C7 . . . . 108.6(2) ?
C2 C3 C8 C7 . . . . 0.3(3) ?
C7 C8 C9 O1 . . . . 124.9(3) ?
C3 C8 C9 O1 . . . . -132.5(3) ?
C7 C8 C9 C10 . . . . -44.2(2) ?
C3 C8 C9 C10 . . . . 58.4(3) ?
O1 C9 C10 C11 . . . . -128.6(3) ?
C8 C9 C10 C11 . . . . 40.7(2) ?
O1 C9 C10 C5 . . . . 132.6(3) ?
C8 C9 C10 C5 . . . . -58.1(3) ?
C4 C5 C10 C9 . . . . -2.9(3) ?
C6 C5 C10 C9 . . . . 104.5(3) ?
C4 C5 C10 C11 . . . . -107.2(3) ?
C6 C5 C10 C11 . . . . 0.3(3) ?
C1A C7 C11 C1B . . . . 10.1(3) ?
C8 C7 C11 C1B . . . . 130.7(3) ?
C1A C7 C11 C10 . . . . -125.5(3) ?
C8 C7 C11 C10 . . . . -4.9(3) ?
C9 C10 C11 C1B . . . . -142.8(4) ?
C5 C10 C11 C1B . . . . -29.9(5) ?
C9 C10 C11 C7 . . . . -21.3(3) ?
C5 C10 C11 C7 . . . . 91.6(3) ?
C4 N1 C12 C13 . . . . -92.8(2) ?
C19 N1 C12 C13 . . . . 144.12(18) ?
N1 C12 C13 C18 . . . . -35.2(3) ?
N1 C12 C13 C14 . . . . 150.2(2) ?
C18 C13 C14 C15 . . . . -1.1(3) ?
C12 C13 C14 C15 . . . . 173.7(2) ?
C13 C14 C15 C16 . . . . 0.6(4) ?
C14 C15 C16 C17 . . . . 0.6(4) ?
C15 C16 C17 C18 . . . . -1.3(4) ?
C16 C17 C18 C13 . . . . 0.8(4) ?
C14 C13 C18 C17 . . . . 0.4(4) ?
C12 C13 C18 C17 . . . . -174.3(2) ?
C4 N1 C19 C20 . . . . 173.10(18) ?
C12 N1 C19 C20 . . . . -64.4(2) ?
N1 C19 C20 C25 . . . . 120.5(2) ?
N1 C19 C20 C21 . . . . -60.8(3) ?
C25 C20 C21 C22 . . . . 0.1(4) ?
C19 C20 C21 C22 . . . . -178.6(2) ?
C20 C21 C22 C23 . . . . 0.2(4) ?
C21 C22 C23 C24 . . . . -0.4(4) ?
C22 C23 C24 C25 . . . . 0.2(4) ?
C23 C24 C25 C20 . . . . 0.1(4) ?
C21 C20 C25 C24 . . . . -0.3(3) ?
C19 C20 C25 C24 . . . . 178.4(2) ?
C6 C2 C1A C7 . . . . -67.4(3) ?
C3 C2 C1A C7 . . . . 46.7(4) ?
C11 C7 C1A C2 . . . . 66.7(3) ?
C8 C7 C1A C2 . . . . -46.9(4) ?
C2 C6 C1B C11 . . . . 83.9(4) ?
C5 C6 C1B C11 . . . . -40.0(5) ?
C7 C11 C1B C6 . . . . -82.9(4) ?
C10 C11 C1B C6 . . . . 40.9(5) ?
