#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/92/2229215.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_2229215
loop_
_publ_author_name
'Maharramov, Abel M.'
'Ismiyev, Arif I.'
'Rashidov, Bahruz A.'
'Rahimova, Gunel M.'
'Allahverdiyev, Mirza A.'
_publ_section_title
;
 rac-Diethyl
 9-hydroxy-9-methyl-7-phenyl-1,4-diazaspiro[4.5]decane-6,8-dicarboxylate
;
_journal_coeditor_code           SI2321
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o291
_journal_paper_doi               10.1107/S1600536810054498
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C21 H30 N2 O5'
_chemical_formula_moiety         'C21 H30 N2 O5'
_chemical_formula_sum            'C21 H30 N2 O5'
_chemical_formula_weight         390.47
_chemical_name_systematic
;
rac-Diethyl
9-hydroxy-9-methyl-7-phenyl-1,4-diazaspiro[4.5]decane-6,8-dicarboxylate
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                103.000(4)
_cell_angle_beta                 97.413(4)
_cell_angle_gamma                97.736(4)
_cell_formula_units_Z            2
_cell_length_a                   9.4140(17)
_cell_length_b                   10.7606(19)
_cell_length_c                   10.7874(19)
_cell_measurement_reflns_used    1499
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.266
_cell_measurement_theta_min      2.406
_cell_volume                     1040.6(3)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2001)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXS97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXL97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω'
_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  0.0649
_diffrn_reflns_av_sigmaI/netI    0.1083
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8475
_diffrn_reflns_theta_full        26.54
_diffrn_reflns_theta_max         26.54
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9868
_exptl_absorpt_correction_T_min  0.9825
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.247
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     288
_refine_ls_number_reflns         4252
_refine_ls_number_restraints     45
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.1328
_refine_ls_R_factor_gt           0.0675
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0700P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1489
_refine_ls_wR_factor_ref         0.1754
_reflns_number_gt                2225
_reflns_number_total             4252
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            si2321.cif
_cod_data_source_block           I
_cod_database_code               2229215
_cod_database_fobs_code          2229215
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
O O1 0.3602(2) 0.2303(2) 0.8120(2) 0.0732(7) Uani d D 1 . .
O O2 0.36432(19) 0.2704(2) 0.61942(18) 0.0567(6) Uani d . 1 . .
O O3 0.91777(17) 0.3860(2) 0.62626(17) 0.0562(6) Uani d D 1 . .
O O4 1.06405(19) 0.4465(3) 0.8161(2) 0.0732(7) Uani d . 1 . .
O O5 0.7805(2) 0.6254(2) 0.68461(18) 0.0491(5) Uani d . 1 . .
H H5O 0.688(3) 0.594(3) 0.660(3) 0.058(9) Uiso d . 1 . .
N N1 0.3905(2) 0.5684(3) 0.8533(2) 0.0424(6) Uani d . 1 . .
H H1N 0.315(3) 0.499(3) 0.833(3) 0.050(8) Uiso d . 1 . .
C C2 0.3457(3) 0.6699(3) 0.7935(3) 0.0564(8) Uani d . 1 . .
H H2A 0.3883 0.7548 0.8481 0.068 Uiso calc R 1 . .
H H2B 0.2407 0.6629 0.7811 0.068 Uiso calc R 1 . .
C C3 0.3994(3) 0.6504(3) 0.6627(3) 0.0560(8) Uani d . 1 . .
H H3A 0.3178 0.6241 0.5923 0.067 Uiso calc R 1 . .
H H3B 0.4564 0.7299 0.6558 0.067 Uiso calc R 1 . .
N N4 0.4897(2) 0.5477(3) 0.6591(2) 0.0429(6) Uani d . 1 . .
H H4N 0.441(3) 0.474(3) 0.615(3) 0.066(11) Uiso d . 1 . .
C C5 0.5167(2) 0.5335(3) 0.7942(2) 0.0364(7) Uani d . 1 A .
C C6 0.5414(2) 0.3967(3) 0.8005(2) 0.0355(6) Uani d . 1 . .
H H6A 0.5591 0.3945 0.8915 0.043 Uiso calc R 1 A .
C C7 0.6766(2) 0.3630(2) 0.7404(2) 0.0342(6) Uani d . 1 A .
H H7A 0.6592 0.3675 0.6501 0.041 Uiso calc R 1 . .
C C8 0.8119(2) 0.4630(3) 0.8092(2) 0.0376(6) Uani d . 1 . .
H H8A 0.8285 0.4572 0.8991 0.045 Uiso calc R 1 A .
C C9 0.7911(2) 0.6047(3) 0.8112(2) 0.0411(7) Uani d . 1 A .
C C10 0.6525(2) 0.6281(3) 0.8664(2) 0.0406(7) Uani d . 1 . .
H H10A 0.6666 0.6229 0.9556 0.049 Uiso calc R 1 A .
H H10B 0.6369 0.7152 0.8654 0.049 Uiso calc R 1 . .
C C11 0.4127(2) 0.2941(3) 0.7330(3) 0.0412(7) Uani d . 1 A .
C C12 0.256(2) 0.1166(13) 0.7402(10) 0.112(8) Uani d PDU 0.46(3) A 1
H H12A 0.3007 0.0637 0.6758 0.134 Uiso calc PR 0.46(3) A 1
H H12B 0.1726 0.1422 0.6967 0.134 Uiso calc PR 0.46(3) A 1
C C13 0.210(3) 0.0405(15) 0.8359(14) 0.132(8) Uani d PDU 0.46(3) A 1
H H13A 0.2952 0.0263 0.8869 0.198 Uiso calc PR 0.46(3) A 1
H H13B 0.1529 -0.0413 0.7897 0.198 Uiso calc PR 0.46(3) A 1
H H13C 0.1541 0.0886 0.8912 0.198 Uiso calc PR 0.46(3) A 1
C C12' 0.2401(8) 0.1223(6) 0.7744(17) 0.094(4) Uani d PDU 0.54(3) A 2
H H12C 0.2007 0.1075 0.6837 0.112 Uiso calc PR 0.54(3) A 2
H H12D 0.1634 0.1405 0.8243 0.112 Uiso calc PR 0.54(3) A 2
C C13' 0.299(2) 0.0036(7) 0.800(2) 0.135(7) Uani d PDU 0.54(3) A 2
H H13D 0.3728 -0.0150 0.7481 0.203 Uiso calc PR 0.54(3) A 2
H H13E 0.2214 -0.0692 0.7781 0.203 Uiso calc PR 0.54(3) A 2
H H13F 0.3400 0.0202 0.8894 0.203 Uiso calc PR 0.54(3) A 2
C C14 0.6973(2) 0.2259(3) 0.7422(2) 0.0410(7) Uani d . 1 . .
C C15 0.6688(3) 0.1281(3) 0.6296(3) 0.0551(8) Uani d . 1 A .
H H15A 0.6359 0.1469 0.5519 0.066 Uiso calc R 1 . .
C C16 0.6883(4) 0.0033(3) 0.6304(4) 0.0686(10) Uani d . 1 . .
H H16A 0.6686 -0.0605 0.5534 0.082 Uiso calc R 1 A .
C C17 0.7361(4) -0.0276(4) 0.7424(4) 0.0756(11) Uani d . 1 A .
H H17A 0.7496 -0.1116 0.7422 0.091 Uiso calc R 1 . .
C C18 0.7639(4) 0.0667(4) 0.8552(4) 0.0831(12) Uani d . 1 . .
H H18A 0.7956 0.0461 0.9322 0.100 Uiso calc R 1 A .
C C19 0.7453(3) 0.1934(3) 0.8562(3) 0.0623(9) Uani d . 1 A .
H H19A 0.7651 0.2565 0.9337 0.075 Uiso calc R 1 . .
C C20 0.9451(3) 0.4310(3) 0.7527(3) 0.0441(7) Uani d . 1 A .
C C21 1.0367(3) 0.3475(3) 0.5612(3) 0.0775(11) Uani d D 1 . .
H H21A 1.1162 0.3383 0.6235 0.093 Uiso calc R 1 . .
H H21B 1.0721 0.4128 0.5184 0.093 Uiso calc R 1 . .
C C22 0.9815(4) 0.2206(4) 0.4639(4) 0.1019(15) Uani d D 1 . .
H H22A 1.0557 0.1982 0.4138 0.153 Uiso calc R 1 . .
H H22B 0.8969 0.2282 0.4079 0.153 Uiso calc R 1 . .
H H22C 0.9568 0.1544 0.5078 0.153 Uiso calc R 1 . .
C C23 0.9203(3) 0.7006(3) 0.8929(3) 0.0595(9) Uani d . 1 . .
H H23A 0.8995 0.7868 0.9026 0.089 Uiso calc R 1 A .
H H23B 1.0042 0.6927 0.8515 0.089 Uiso calc R 1 . .
H H23C 0.9391 0.6829 0.9762 0.089 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'
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
C11 O1 C12 . . 110.4(5) ?
C11 O1 C12' . . 124.8(8) ?
C12 O1 C12' . . 16.3(9) ?
C20 O3 C21 . . 117.9(2) ?
C9 O5 H5O . . 97(2) ?
C2 N1 C5 . . 104.2(2) ?
C2 N1 H1N . . 108.9(19) ?
C5 N1 H1N . . 111.4(16) ?
N1 C2 C3 . . 107.0(2) ?
N1 C2 H2A . . 110.3 ?
C3 C2 H2A . . 110.3 ?
N1 C2 H2B . . 110.3 ?
C3 C2 H2B . . 110.3 ?
H2A C2 H2B . . 108.6 ?
N4 C3 C2 . . 105.8(2) ?
N4 C3 H3A . . 110.6 ?
C2 C3 H3A . . 110.6 ?
N4 C3 H3B . . 110.6 ?
C2 C3 H3B . . 110.6 ?
H3A C3 H3B . . 108.7 ?
C3 N4 C5 . . 105.42(19) ?
C3 N4 H4N . . 111(2) ?
C5 N4 H4N . . 105(2) ?
N1 C5 N4 . . 106.77(18) ?
N1 C5 C10 . . 109.25(19) ?
N4 C5 C10 . . 108.6(2) ?
N1 C5 C6 . . 111.7(2) ?
N4 C5 C6 . . 112.5(2) ?
C10 C5 C6 . . 107.91(19) ?
C11 C6 C5 . . 112.78(19) ?
C11 C6 C7 . . 108.50(18) ?
C5 C6 C7 . . 110.9(2) ?
C11 C6 H6A . . 108.2 ?
C5 C6 H6A . . 108.2 ?
C7 C6 H6A . . 108.2 ?
C14 C7 C8 . . 112.20(19) ?
C14 C7 C6 . . 110.7(2) ?
C8 C7 C6 . . 110.38(18) ?
C14 C7 H7A . . 107.8 ?
C8 C7 H7A . . 107.8 ?
C6 C7 H7A . . 107.8 ?
C20 C8 C7 . . 111.2(2) ?
C20 C8 C9 . . 111.4(2) ?
C7 C8 C9 . . 112.87(18) ?
C20 C8 H8A . . 107.0 ?
C7 C8 H8A . . 107.0 ?
C9 C8 H8A . . 107.0 ?
O5 C9 C23 . . 106.6(2) ?
O5 C9 C10 . . 110.33(19) ?
C23 C9 C10 . . 110.1(2) ?
O5 C9 C8 . . 110.8(2) ?
C23 C9 C8 . . 110.9(2) ?
C10 C9 C8 . . 108.1(2) ?
C5 C10 C9 . . 114.35(19) ?
C5 C10 H10A . . 108.7 ?
C9 C10 H10A . . 108.7 ?
C5 C10 H10B . . 108.7 ?
C9 C10 H10B . . 108.7 ?
H10A C10 H10B . . 107.6 ?
O2 C11 O1 . . 123.4(3) ?
O2 C11 C6 . . 124.7(3) ?
O1 C11 C6 . . 111.8(2) ?
O1 C12 C13 . . 107.8(3) ?
O1 C12 H12A . . 110.2 ?
C13 C12 H12A . . 110.2 ?
O1 C12 H12B . . 110.2 ?
C13 C12 H12B . . 110.2 ?
H12A C12 H12B . . 108.5 ?
O1 C12' C13' . . 107.4(3) ?
O1 C12' H12C . . 110.2 ?
C13' C12' H12C . . 110.2 ?
O1 C12' H12D . . 110.2 ?
C13' C12' H12D . . 110.2 ?
H12C C12' H12D . . 108.5 ?
C12' C13' H13D . . 109.5 ?
C12' C13' H13E . . 109.5 ?
H13D C13' H13E . . 109.5 ?
C12' C13' H13F . . 109.5 ?
H13D C13' H13F . . 109.5 ?
H13E C13' H13F . . 109.5 ?
C15 C14 C19 . . 117.4(3) ?
C15 C14 C7 . . 121.0(2) ?
C19 C14 C7 . . 121.6(2) ?
C16 C15 C14 . . 121.3(3) ?
C16 C15 H15A . . 119.3 ?
C14 C15 H15A . . 119.3 ?
C17 C16 C15 . . 120.9(3) ?
C17 C16 H16A . . 119.6 ?
C15 C16 H16A . . 119.6 ?
C16 C17 C18 . . 119.1(3) ?
C16 C17 H17A . . 120.4 ?
C18 C17 H17A . . 120.4 ?
C17 C18 C19 . . 120.9(4) ?
C17 C18 H18A . . 119.6 ?
C19 C18 H18A . . 119.6 ?
C14 C19 C18 . . 120.4(3) ?
C14 C19 H19A . . 119.8 ?
C18 C19 H19A . . 119.8 ?
O4 C20 O3 . . 123.6(2) ?
O4 C20 C8 . . 123.6(3) ?
O3 C20 C8 . . 112.8(2) ?
O3 C21 C22 . . 108.4(2) ?
O3 C21 H21A . . 110.0 ?
C22 C21 H21A . . 110.0 ?
O3 C21 H21B . . 110.0 ?
C22 C21 H21B . . 110.0 ?
H21A C21 H21B . . 108.4 ?
C21 C22 H22A . . 109.5 ?
C21 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
C21 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
C9 C23 H23A . . 109.5 ?
C9 C23 H23B . . 109.5 ?
H23A C23 H23B . . 109.5 ?
C9 C23 H23C . . 109.5 ?
H23A C23 H23C . . 109.5 ?
H23B C23 H23C . . 109.5 ?
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 C11 . 1.312(4) ?
O1 C12 . 1.452(3) ?
O1 C12' . 1.452(3) ?
O2 C11 . 1.207(3) ?
O3 C20 . 1.319(3) ?
O3 C21 . 1.454(2) ?
O4 C20 . 1.204(3) ?
O5 C9 . 1.426(3) ?
O5 H5O . 0.87(3) ?
N1 C2 . 1.469(4) ?
N1 C5 . 1.472(3) ?
N1 H1N . 0.93(3) ?
C2 C3 . 1.539(4) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 N4 . 1.479(3) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
N4 C5 . 1.491(3) ?
N4 H4N . 0.86(3) ?
C5 C10 . 1.521(4) ?
C5 C6 . 1.536(4) ?
C6 C11 . 1.507(4) ?
C6 C7 . 1.550(3) ?
C6 H6A . 0.9800 ?
C7 C14 . 1.518(4) ?
C7 C8 . 1.536(3) ?
C7 H7A . 0.9800 ?
C8 C20 . 1.511(3) ?
C8 C9 . 1.558(4) ?
C8 H8A . 0.9800 ?
C9 C23 . 1.515(4) ?
C9 C10 . 1.531(3) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C12 C13 . 1.524(3) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
C12' C13' . 1.525(3) ?
C12' H12C . 0.9700 ?
C12' H12D . 0.9700 ?
C13' H13D . 0.9600 ?
C13' H13E . 0.9600 ?
C13' H13F . 0.9600 ?
C14 C15 . 1.385(4) ?
C14 C19 . 1.390(4) ?
C15 C16 . 1.382(5) ?
C15 H15A . 0.9300 ?
C16 C17 . 1.361(5) ?
C16 H16A . 0.9300 ?
C17 C18 . 1.367(5) ?
C17 H17A . 0.9300 ?
C18 C19 . 1.395(5) ?
C18 H18A . 0.9300 ?
C19 H19A . 0.9300 ?
C21 C22 . 1.503(3) ?
C21 H21A . 0.9700 ?
C21 H21B . 0.9700 ?
C22 H22A . 0.9600 ?
C22 H22B . 0.9600 ?
C22 H22C . 0.9600 ?
C23 H23A . 0.9600 ?
C23 H23B . 0.9600 ?
C23 H23C . 0.9600 ?
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
_geom_hbond_publ_flag
O5 H5O N4 1_555 0.87(3) 1.87(3) 2.714(4) 163(3) yes
N4 H4N O2 1_555 0.86(4) 2.23(4) 2.971(4) 144(4) yes
N1 H1N O4 1_455 0.93(3) 2.32(3) 3.113(3) 143 yes
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
C5 N1 C2 C3 . . . . 24.6(3) ?
N1 C2 C3 N4 . . . . -6.9(3) ?
C2 C3 N4 C5 . . . . -13.4(3) ?
C2 N1 C5 N4 . . . . -33.6(3) ?
C2 N1 C5 C10 . . . . 83.7(3) ?
C2 N1 C5 C6 . . . . -157.0(2) ?
C3 N4 C5 N1 . . . . 29.4(3) ?
C3 N4 C5 C10 . . . . -88.3(2) ?
C3 N4 C5 C6 . . . . 152.3(2) ?
N1 C5 C6 C11 . . . . 59.3(3) ?
N4 C5 C6 C11 . . . . -60.8(3) ?
C10 C5 C6 C11 . . . . 179.39(18) ?
N1 C5 C6 C7 . . . . -178.81(18) ?
N4 C5 C6 C7 . . . . 61.1(2) ?
C10 C5 C6 C7 . . . . -58.7(2) ?
C11 C6 C7 C14 . . . . -53.4(3) ?
C5 C6 C7 C14 . . . . -177.81(19) ?
C11 C6 C7 C8 . . . . -178.3(2) ?
C5 C6 C7 C8 . . . . 57.3(3) ?
C14 C7 C8 C20 . . . . 55.4(3) ?
C6 C7 C8 C20 . . . . 179.4(2) ?
C14 C7 C8 C9 . . . . -178.55(19) ?
C6 C7 C8 C9 . . . . -54.5(3) ?
C20 C8 C9 O5 . . . . 57.6(3) ?
C7 C8 C9 O5 . . . . -68.3(2) ?
C20 C8 C9 C23 . . . . -60.6(3) ?
C7 C8 C9 C23 . . . . 173.5(2) ?
C20 C8 C9 C10 . . . . 178.6(2) ?
C7 C8 C9 C10 . . . . 52.7(3) ?
N1 C5 C10 C9 . . . . -178.1(2) ?
N4 C5 C10 C9 . . . . -62.0(3) ?
C6 C5 C10 C9 . . . . 60.2(3) ?
O5 C9 C10 C5 . . . . 64.7(3) ?
C23 C9 C10 C5 . . . . -177.9(2) ?
C8 C9 C10 C5 . . . . -56.6(3) ?
C12 O1 C11 O2 . . . . 9.9(12) ?
C12' O1 C11 O2 . . . . 1.2(6) ?
C12 O1 C11 C6 . . . . -168.6(11) ?
C12' O1 C11 C6 . . . . -177.4(5) ?
C5 C6 C11 O2 . . . . 61.6(3) ?
C7 C6 C11 O2 . . . . -61.6(3) ?
C5 C6 C11 O1 . . . . -119.8(2) ?
C7 C6 C11 O1 . . . . 116.9(2) ?
C11 O1 C12 C13 . . . . 175(2) ?
C12' O1 C12 C13 . . . . -32(3) ?
C11 O1 C12' C13' . . . . 116.7(18) ?
C12 O1 C12' C13' . . . . 86(4) ?
C8 C7 C14 C15 . . . . -128.3(2) ?
C6 C7 C14 C15 . . . . 107.9(3) ?
C8 C7 C14 C19 . . . . 51.7(3) ?
C6 C7 C14 C19 . . . . -72.1(3) ?
C19 C14 C15 C16 . . . . -0.5(4) ?
C7 C14 C15 C16 . . . . 179.6(3) ?
C14 C15 C16 C17 . . . . 0.1(5) ?
C15 C16 C17 C18 . . . . 0.4(5) ?
C16 C17 C18 C19 . . . . -0.6(6) ?
C15 C14 C19 C18 . . . . 0.2(5) ?
C7 C14 C19 C18 . . . . -179.8(3) ?
C17 C18 C19 C14 . . . . 0.3(6) ?
C21 O3 C20 O4 . . . . 3.1(4) ?
C21 O3 C20 C8 . . . . -177.9(2) ?
C7 C8 C20 O4 . . . . -142.5(3) ?
C9 C8 C20 O4 . . . . 90.6(3) ?
C7 C8 C20 O3 . . . . 38.5(3) ?
C9 C8 C20 O3 . . . . -88.4(3) ?
C20 O3 C21 C22 . . . . 135.8(3) ?
