#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/78/2227826.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2227826
loop_
_publ_author_name
'Wang, Kai'
'Zhang, Ye'
'Yi, Xiang-Hui'
'Zhang, Yong'
'Pan, Ying-Ming'
_publ_section_title
;
 Methyl 7-oxo-12-propylamino-13-nitrodeisopropyldehydroabietate
;
_journal_coeditor_code           NG5010
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2604
_journal_paper_doi               10.1107/S1600536810032824
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C21 H28 N2 O5'
_chemical_formula_moiety         'C21 H28 N2 O5'
_chemical_formula_sum            'C21 H28 N2 O5'
_chemical_formula_weight         388.45
_chemical_name_common
;
Methyl 7-oxo-12-propylamino-13-nitrodeisopropyldehydroabietate
;
_chemical_name_systematic
;
methyl 1,4a-dimethyl-7-nitro-9-oxo-6-propylamino-
1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylate
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.2915(15)
_cell_length_b                   11.344(2)
_cell_length_c                   20.288(4)
_cell_measurement_reflns_used    6184
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_cell_volume                     1908.3(6)
_computing_cell_refinement       'CrystalClear (Rigaku, 1999)'
_computing_data_collection       'CrystalClear (Rigaku, 1999)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2000)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      223(2)
_diffrn_detector_area_resol_mean 14.63
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_av_sigmaI/netI    0.0491
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            9263
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.04
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Jacobson, 1998)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.201
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.193
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         2492
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.193
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0614
_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)+(0.0400P)²+0.3656P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1177
_refine_ls_wR_factor_ref         0.1215
_reflns_number_gt                2249
_reflns_number_total             2492
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            ng5010.cif
_cod_data_source_block           I
_cod_database_code               2227826
_cod_database_fobs_code          2227826
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, 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 -0.0800(3) 0.5805(2) 0.50671(13) 0.0413(7) Uani d . 1 . .
O O2 0.1082(3) 0.8201(2) 0.32927(14) 0.0428(7) Uani d . 1 . .
O O3 0.3574(3) 0.8723(2) 0.31899(13) 0.0374(6) Uani d . 1 . .
O O4 0.1294(4) 0.3814(3) 0.75394(15) 0.0594(9) Uani d . 1 . .
O O5 0.2387(3) 0.5514(2) 0.72342(13) 0.0393(6) Uani d . 1 . .
N N1 0.5809(3) 0.7320(3) 0.37018(15) 0.0301(7) Uani d . 1 . .
H H1A 0.552(4) 0.784(3) 0.3368(19) 0.034(10) Uiso d . 1 . .
N N2 0.2510(3) 0.8110(3) 0.34543(14) 0.0296(6) Uani d . 1 . .
C C1 0.4799(4) 0.5968(3) 0.45202(16) 0.0273(7) Uani d . 1 . .
H H1B 0.5847 0.5672 0.4583 0.033 Uiso calc R 1 . .
C C2 0.4562(4) 0.6880(3) 0.40463(16) 0.0261(7) Uani d . 1 . .
C C3 0.2948(4) 0.7264(3) 0.39580(16) 0.0264(7) Uani d . 1 . .
C C4 0.1710(4) 0.6826(3) 0.43411(16) 0.0272(7) Uani d . 1 . .
H H4 0.0662 0.7126 0.4284 0.033 Uiso calc R 1 . .
C C5 0.1976(4) 0.5958(3) 0.48066(16) 0.0259(7) Uani d . 1 . .
C C6 0.3556(4) 0.5500(3) 0.48907(15) 0.0249(7) Uani d . 1 . .
C C7 0.0594(4) 0.5512(3) 0.51883(17) 0.0306(8) Uani d . 1 . .
C C8 0.0933(4) 0.4657(3) 0.57383(17) 0.0291(7) Uani d . 1 . .
H H8A 0.0626 0.3863 0.5595 0.035 Uiso calc R 1 . .
H H8B 0.0262 0.4863 0.6119 0.035 Uiso calc R 1 . .
C C9 0.2698(4) 0.4647(3) 0.59499(15) 0.0255(7) Uani d . 1 . .
H H9 0.2930 0.5455 0.6106 0.031 Uiso calc R 1 . .
C C10 0.2965(4) 0.3826(3) 0.65599(17) 0.0285(7) Uani d . 1 . .
C C11 0.4779(4) 0.3807(3) 0.67347(18) 0.0336(8) Uani d . 1 . .
H H11A 0.5099 0.4585 0.6899 0.040 Uiso calc R 1 . .
H H11B 0.4962 0.3233 0.7088 0.040 Uiso calc R 1 . .
C C12 0.5822(5) 0.3488(4) 0.61471(19) 0.0382(9) Uani d . 1 . .
H H12A 0.5536 0.2697 0.5992 0.046 Uiso calc R 1 . .
H H12B 0.6958 0.3477 0.6281 0.046 Uiso calc R 1 . .
C C13 0.5592(4) 0.4378(3) 0.55853(18) 0.0339(8) Uani d . 1 . .
H H13A 0.6285 0.4154 0.5214 0.041 Uiso calc R 1 . .
H H13B 0.5933 0.5160 0.5737 0.041 Uiso calc R 1 . .
C C14 0.3833(4) 0.4444(3) 0.53470(16) 0.0264(7) Uani d . 1 . .
C C15 0.7445(4) 0.6817(3) 0.36949(17) 0.0294(7) Uani d . 1 . .
H H15A 0.7771 0.6639 0.4148 0.035 Uiso calc R 1 . .
H H15B 0.8197 0.7406 0.3520 0.035 Uiso calc R 1 . .
C C16 0.7571(4) 0.5698(3) 0.32818(18) 0.0346(8) Uani d . 1 . .
H H16A 0.7319 0.5881 0.2821 0.042 Uiso calc R 1 . .
H H16B 0.6781 0.5120 0.3439 0.042 Uiso calc R 1 . .
C C17 0.9260(4) 0.5170(3) 0.33244(19) 0.0364(9) Uani d . 1 . .
H H17A 1.0049 0.5762 0.3202 0.055 Uiso calc R 1 . .
H H17B 0.9340 0.4504 0.3026 0.055 Uiso calc R 1 . .
H H17C 0.9465 0.4909 0.3772 0.055 Uiso calc R 1 . .
C C18 0.2105(4) 0.4364(3) 0.71584(18) 0.0326(8) Uani d . 1 . .
C C19 0.1741(5) 0.6042(4) 0.7827(2) 0.0500(11) Uani d . 1 . .
H H19A 0.0574 0.5989 0.7821 0.075 Uiso calc R 1 . .
H H19B 0.2061 0.6864 0.7848 0.075 Uiso calc R 1 . .
H H19C 0.2156 0.5627 0.8210 0.075 Uiso calc R 1 . .
C C20 0.2305(5) 0.2577(3) 0.6477(2) 0.0412(9) Uani d . 1 . .
H H20A 0.2449 0.2143 0.6885 0.062 Uiso calc R 1 . .
H H20B 0.2882 0.2182 0.6125 0.062 Uiso calc R 1 . .
H H20C 0.1167 0.2613 0.6369 0.062 Uiso calc R 1 . .
C C21 0.3452(5) 0.3342(3) 0.49327(18) 0.0376(9) Uani d . 1 . .
H H21A 0.4110 0.3344 0.4538 0.056 Uiso calc R 1 . .
H H21B 0.2321 0.3347 0.4811 0.056 Uiso calc R 1 . .
H H21C 0.3684 0.2640 0.5189 0.056 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
C18 O5 C19 . . 115.8(3) ?
C2 N1 C15 . . 124.8(3) ?
C2 N1 H1A . . 115(2) ?
C15 N1 H1A . . 118(2) ?
O2 N2 O3 . . 121.3(3) ?
O2 N2 C3 . . 119.0(3) ?
O3 N2 C3 . . 119.7(3) ?
C6 C1 C2 . . 122.8(3) ?
C6 C1 H1B . . 118.6 ?
C2 C1 H1B . . 118.6 ?
N1 C2 C3 . . 123.1(3) ?
N1 C2 C1 . . 120.9(3) ?
C3 C2 C1 . . 116.0(3) ?
C4 C3 C2 . . 121.4(3) ?
C4 C3 N2 . . 116.7(3) ?
C2 C3 N2 . . 122.0(3) ?
C3 C4 C5 . . 121.5(3) ?
C3 C4 H4 . . 119.3 ?
C5 C4 H4 . . 119.3 ?
C4 C5 C6 . . 119.3(3) ?
C4 C5 C7 . . 118.7(3) ?
C6 C5 C7 . . 122.0(3) ?
C1 C6 C5 . . 118.9(3) ?
C1 C6 C14 . . 121.1(3) ?
C5 C6 C14 . . 119.8(3) ?
O1 C7 C5 . . 122.3(3) ?
O1 C7 C8 . . 119.9(3) ?
C5 C7 C8 . . 117.8(3) ?
C7 C8 C9 . . 113.1(3) ?
C7 C8 H8A . . 109.0 ?
C9 C8 H8A . . 109.0 ?
C7 C8 H8B . . 109.0 ?
C9 C8 H8B . . 109.0 ?
H8A C8 H8B . . 107.8 ?
C8 C9 C14 . . 111.1(3) ?
C8 C9 C10 . . 111.3(3) ?
C14 C9 C10 . . 116.6(3) ?
C8 C9 H9 . . 105.7 ?
C14 C9 H9 . . 105.7 ?
C10 C9 H9 . . 105.7 ?
C20 C10 C18 . . 106.8(3) ?
C20 C10 C11 . . 111.1(3) ?
C18 C10 C11 . . 106.1(3) ?
C20 C10 C9 . . 114.5(3) ?
C18 C10 C9 . . 108.9(3) ?
C11 C10 C9 . . 109.2(3) ?
C12 C11 C10 . . 112.2(3) ?
C12 C11 H11A . . 109.2 ?
C10 C11 H11A . . 109.2 ?
C12 C11 H11B . . 109.2 ?
C10 C11 H11B . . 109.2 ?
H11A C11 H11B . . 107.9 ?
C11 C12 C13 . . 110.8(3) ?
C11 C12 H12A . . 109.5 ?
C13 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
C13 C12 H12B . . 109.5 ?
H12A C12 H12B . . 108.1 ?
C12 C13 C14 . . 112.5(3) ?
C12 C13 H13A . . 109.1 ?
C14 C13 H13A . . 109.1 ?
C12 C13 H13B . . 109.1 ?
C14 C13 H13B . . 109.1 ?
H13A C13 H13B . . 107.8 ?
C6 C14 C13 . . 111.8(3) ?
C6 C14 C21 . . 105.9(3) ?
C13 C14 C21 . . 109.0(3) ?
C6 C14 C9 . . 105.6(3) ?
C13 C14 C9 . . 109.4(3) ?
C21 C14 C9 . . 115.1(3) ?
N1 C15 C16 . . 113.0(3) ?
N1 C15 H15A . . 109.0 ?
C16 C15 H15A . . 109.0 ?
N1 C15 H15B . . 109.0 ?
C16 C15 H15B . . 109.0 ?
H15A C15 H15B . . 107.8 ?
C15 C16 C17 . . 111.0(3) ?
C15 C16 H16A . . 109.4 ?
C17 C16 H16A . . 109.4 ?
C15 C16 H16B . . 109.4 ?
C17 C16 H16B . . 109.4 ?
H16A C16 H16B . . 108.0 ?
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 ?
O4 C18 O5 . . 122.2(4) ?
O4 C18 C10 . . 124.3(3) ?
O5 C18 C10 . . 113.5(3) ?
O5 C19 H19A . . 109.5 ?
O5 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
O5 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C10 C20 H20A . . 109.5 ?
C10 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C10 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
C14 C21 H21A . . 109.5 ?
C14 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
C14 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 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 C7 . 1.227(4) ?
O2 N2 . 1.233(3) ?
O3 N2 . 1.245(3) ?
O4 C18 . 1.200(4) ?
O5 C18 . 1.334(4) ?
O5 C19 . 1.447(4) ?
N1 C2 . 1.344(4) ?
N1 C15 . 1.472(4) ?
N1 H1A . 0.93(4) ?
N2 C3 . 1.448(4) ?
C1 C6 . 1.382(4) ?
C1 C2 . 1.426(5) ?
C1 H1B . 0.9400 ?
C2 C3 . 1.418(4) ?
C3 C4 . 1.380(5) ?
C4 C5 . 1.383(5) ?
C4 H4 . 0.9400 ?
C5 C6 . 1.419(4) ?
C5 C7 . 1.472(4) ?
C6 C14 . 1.531(5) ?
C7 C8 . 1.505(5) ?
C8 C9 . 1.525(4) ?
C8 H8A . 0.9800 ?
C8 H8B . 0.9800 ?
C9 C14 . 1.560(4) ?
C9 C10 . 1.564(5) ?
C9 H9 . 0.9900 ?
C10 C20 . 1.529(5) ?
C10 C18 . 1.535(5) ?
C10 C11 . 1.545(5) ?
C11 C12 . 1.517(5) ?
C11 H11A . 0.9800 ?
C11 H11B . 0.9800 ?
C12 C13 . 1.535(5) ?
C12 H12A . 0.9800 ?
C12 H12B . 0.9800 ?
C13 C14 . 1.539(5) ?
C13 H13A . 0.9800 ?
C13 H13B . 0.9800 ?
C14 C21 . 1.540(5) ?
C15 C16 . 1.525(5) ?
C15 H15A . 0.9800 ?
C15 H15B . 0.9800 ?
C16 C17 . 1.525(5) ?
C16 H16A . 0.9800 ?
C16 H16B . 0.9800 ?
C17 H17A . 0.9700 ?
C17 H17B . 0.9700 ?
C17 H17C . 0.9700 ?
C19 H19A . 0.9700 ?
C19 H19B . 0.9700 ?
C19 H19C . 0.9700 ?
C20 H20A . 0.9700 ?
C20 H20B . 0.9700 ?
C20 H20C . 0.9700 ?
C21 H21A . 0.9700 ?
C21 H21B . 0.9700 ?
C21 H21C . 0.9700 ?
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 H1A O3 . 0.93(4) 1.94(4) 2.654(4) 133(3)
C8 H8B O3 2_466 0.98 2.55 3.454(4) 153.5
C15 H15A O1 1_655 0.98 2.40 3.344(4) 161.0
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C15 N1 C2 C3 . . . . -169.2(3) ?
C15 N1 C2 C1 . . . . 9.6(5) ?
C6 C1 C2 N1 . . . . 179.2(3) ?
C6 C1 C2 C3 . . . . -2.0(5) ?
N1 C2 C3 C4 . . . . -177.2(3) ?
C1 C2 C3 C4 . . . . 4.0(5) ?
N1 C2 C3 N2 . . . . 4.2(5) ?
C1 C2 C3 N2 . . . . -174.6(3) ?
O2 N2 C3 C4 . . . . -15.9(5) ?
O3 N2 C3 C4 . . . . 164.6(3) ?
O2 N2 C3 C2 . . . . 162.7(3) ?
O3 N2 C3 C2 . . . . -16.7(5) ?
C2 C3 C4 C5 . . . . -3.0(5) ?
N2 C3 C4 C5 . . . . 175.7(3) ?
C3 C4 C5 C6 . . . . -0.3(5) ?
C3 C4 C5 C7 . . . . -178.7(3) ?
C2 C1 C6 C5 . . . . -1.1(5) ?
C2 C1 C6 C14 . . . . 174.2(3) ?
C4 C5 C6 C1 . . . . 2.3(5) ?
C7 C5 C6 C1 . . . . -179.4(3) ?
C4 C5 C6 C14 . . . . -173.1(3) ?
C7 C5 C6 C14 . . . . 5.2(5) ?
C4 C5 C7 O1 . . . . 6.8(5) ?
C6 C5 C7 O1 . . . . -171.5(3) ?
C4 C5 C7 C8 . . . . -174.0(3) ?
C6 C5 C7 C8 . . . . 7.7(5) ?
O1 C7 C8 C9 . . . . -164.0(3) ?
C5 C7 C8 C9 . . . . 16.8(4) ?
C7 C8 C9 C14 . . . . -53.1(4) ?
C7 C8 C9 C10 . . . . 175.2(3) ?
C8 C9 C10 C20 . . . . 52.4(4) ?
C14 C9 C10 C20 . . . . -76.4(4) ?
C8 C9 C10 C18 . . . . -67.0(3) ?
C14 C9 C10 C18 . . . . 164.2(3) ?
C8 C9 C10 C11 . . . . 177.6(3) ?
C14 C9 C10 C11 . . . . 48.8(4) ?
C20 C10 C11 C12 . . . . 73.9(4) ?
C18 C10 C11 C12 . . . . -170.4(3) ?
C9 C10 C11 C12 . . . . -53.2(4) ?
C10 C11 C12 C13 . . . . 59.8(4) ?
C11 C12 C13 C14 . . . . -59.2(4) ?
C1 C6 C14 C13 . . . . 26.8(4) ?
C5 C6 C14 C13 . . . . -157.9(3) ?
C1 C6 C14 C21 . . . . -91.8(4) ?
C5 C6 C14 C21 . . . . 83.5(4) ?
C1 C6 C14 C9 . . . . 145.7(3) ?
C5 C6 C14 C9 . . . . -39.0(4) ?
C12 C13 C14 C6 . . . . 168.4(3) ?
C12 C13 C14 C21 . . . . -74.8(4) ?
C12 C13 C14 C9 . . . . 51.8(4) ?
C8 C9 C14 C6 . . . . 62.4(3) ?
C10 C9 C14 C6 . . . . -168.7(3) ?
C8 C9 C14 C13 . . . . -177.2(3) ?
C10 C9 C14 C13 . . . . -48.3(4) ?
C8 C9 C14 C21 . . . . -54.0(4) ?
C10 C9 C14 C21 . . . . 74.9(4) ?
C2 N1 C15 C16 . . . . 75.2(4) ?
N1 C15 C16 C17 . . . . -176.5(3) ?
C19 O5 C18 O4 . . . . 3.8(5) ?
C19 O5 C18 C10 . . . . -173.9(3) ?
C20 C10 C18 O4 . . . . 11.4(5) ?
C11 C10 C18 O4 . . . . -107.1(4) ?
C9 C10 C18 O4 . . . . 135.5(4) ?
C20 C10 C18 O5 . . . . -170.8(3) ?
C11 C10 C18 O5 . . . . 70.6(4) ?
C9 C10 C18 O5 . . . . -46.8(4) ?
