#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/13/2221382.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_2221382
loop_
_publ_author_name
'Li, Yu-Feng'
'Qian, Yi'
'Yin, Li-He'
'Lv, Ran'
'Zhu, Hong-Jun'
_publ_section_title
(9S,13R,14R)-7,8-Didehydro-3,4,7-trimethoxy-17-methylmorphinan-6-one
_journal_coeditor_code           HK2561
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o689
_journal_paper_doi               10.1107/S1600536808040749
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C20 H25 N O4'
_chemical_formula_moiety         'C20 H25 N O4'
_chemical_formula_sum            'C20 H25 N O4'
_chemical_formula_weight         343.41
_chemical_name_systematic
;
(9S,13R,14S)-7,8-didehydro-3,4,7-trimethoxy-N-methyl-morphinan-6-one
;
_space_group_IT_number           145
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  'P 32'
_symmetry_space_group_name_H-M   'P 32'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            3
_cell_length_a                   10.9590(15)
_cell_length_b                   10.9590(15)
_cell_length_c                   12.726(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      10
_cell_volume                     1323.6(4)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_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      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0369
_diffrn_reflns_av_sigmaI/netI    0.0443
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2008
_diffrn_reflns_theta_full        25.95
_diffrn_reflns_theta_max         25.95
_diffrn_reflns_theta_min         2.15
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9736
_exptl_absorpt_correction_T_min  0.9651
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.446
_refine_diff_density_min         -0.222
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         1728
_refine_ls_number_restraints     44
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0902
_refine_ls_R_factor_gt           0.0704
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1178P)²+0.4849P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1874
_refine_ls_wR_factor_ref         0.2082
_reflns_number_gt                1281
_reflns_number_total             1728
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            hk2561.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Trigonal' changed to 'trigonal' according
to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Trigonal' changed to 'trigonal'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_Hall     'P 32 '
_cod_original_sg_symbol_H-M      'P 32 '
_cod_database_code               2221382
_cod_database_fobs_code          2221382
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
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 0.7890(7) 0.2303(6) 0.0383(5) 0.0855(17) Uani d . 1 . .
O O2 0.8937(7) 0.0744(5) 0.1262(6) 0.093(2) Uani d . 1 . .
O O3 1.2532(6) 0.7232(5) -0.1456(4) 0.0719(13) Uani d . 1 . .
O O4 1.0260(6) 0.4750(6) -0.1870(4) 0.0765(15) Uani d . 1 . .
N N 0.9014(7) 0.6779(6) 0.2458(4) 0.0607(14) Uani d . 1 . .
C C18 0.7882(16) 0.1603(14) -0.0423(8) 0.123(4) Uani d . 1 . .
H H18A 0.6976 0.1188 -0.0757 0.185 Uiso calc R 1 . .
H H18B 0.8071 0.0873 -0.0210 0.185 Uiso calc R 1 . .
H H18C 0.8595 0.2222 -0.0909 0.185 Uiso calc R 1 . .
C C17 0.9251(11) -0.0152(9) 0.1821(8) 0.093(3) Uani d . 1 . .
H H17A 0.8722 -0.1088 0.1540 0.139 Uiso calc R 1 . .
H H17B 0.9009 -0.0159 0.2547 0.139 Uiso calc R 1 . .
H H17C 1.0240 0.0172 0.1763 0.139 Uiso calc R 1 . .
C C3 0.9567(7) 0.2137(7) 0.1507(5) 0.0592(16) Uani d U 1 . .
C C4 0.9072(7) 0.2945(7) 0.0963(5) 0.0563(15) Uani d U 1 . .
C C12 0.9634(6) 0.4366(6) 0.1177(4) 0.0436(12) Uani d . 1 . .
C C11 1.0594(6) 0.4957(7) 0.1981(4) 0.0470(13) Uani d . 1 . .
C C1 1.1056(8) 0.4155(8) 0.2521(5) 0.0590(17) Uani d . 1 . .
H H1A 1.1723 0.4579 0.3051 0.071 Uiso calc R 1 . .
C C2 1.0563(8) 0.2771(8) 0.2294(6) 0.0653(19) Uani d . 1 . .
H H2A 1.0890 0.2259 0.2663 0.078 Uiso calc R 1 . .
C C19 1.3723(8) 0.8546(9) -0.1173(7) 0.082(2) Uani d . 1 . .
H H19A 1.4485 0.8759 -0.1646 0.123 Uiso calc R 1 . .
H H19B 1.4005 0.8490 -0.0468 0.123 Uiso calc R 1 . .
H H19C 1.3480 0.9274 -0.1212 0.123 Uiso calc R 1 . .
C C20 0.9242(11) 0.7233(10) 0.3554(6) 0.085(2) Uani d . 1 . .
H H20A 0.9976 0.8201 0.3594 0.127 Uiso calc R 1 . .
H H20B 0.9511 0.6659 0.3949 0.127 Uiso calc R 1 . .
H H20C 0.8388 0.7138 0.3840 0.127 Uiso calc R 1 . .
C C15 0.7923(7) 0.5297(7) 0.2337(5) 0.0569(16) Uani d D 1 . .
H H15A 0.7056 0.5152 0.2655 0.068 Uiso calc R 1 . .
H H15B 0.8213 0.4711 0.2709 0.068 Uiso calc R 1 . .
C C16 0.7647(6) 0.4843(7) 0.1193(5) 0.0531(15) Uani d D 1 . .
H H16A 0.7221 0.5323 0.0842 0.064 Uiso calc R 1 . .
H H16B 0.6994 0.3837 0.1154 0.064 Uiso calc R 1 . .
C C13 0.9034(6) 0.5194(6) 0.0638(5) 0.0461(13) Uani d . 1 . .
C C5 0.8825(7) 0.4990(7) -0.0559(5) 0.0533(14) Uani d U 1 . .
H H5A 0.8155 0.4009 -0.0706 0.064 Uiso calc R 1 . .
H H5B 0.8429 0.5550 -0.0819 0.064 Uiso calc R 1 . .
C C6 1.0162(7) 0.5401(7) -0.1131(5) 0.0557(15) Uani d U 1 . .
C C7 1.1414(7) 0.6762(7) -0.0771(5) 0.0541(14) Uani d U 1 . .
C C8 1.1330(7) 0.7371(6) 0.0109(5) 0.0532(15) Uani d U 1 . .
H H8A 1.2119 0.8200 0.0328 0.064 Uiso calc R 1 . .
C C14 1.0026(7) 0.6780(6) 0.0759(4) 0.0470(13) Uani d . 1 . .
H H14A 0.9502 0.7236 0.0519 0.056 Uiso calc R 1 . .
C C9 1.0334(7) 0.7134(7) 0.1920(5) 0.0549(15) Uani d . 1 . .
H H9A 1.0938 0.8159 0.1966 0.066 Uiso calc R 1 . .
C C10 1.1204(8) 0.6499(7) 0.2307(5) 0.0593(16) Uani d . 1 . .
H H10A 1.1262 0.6562 0.3067 0.071 Uiso calc R 1 . .
H H10B 1.2153 0.7046 0.2031 0.071 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 O1 C4 . . 118.1(9) ?
C3 O2 C17 . . 120.6(7) ?
C7 O3 C19 . . 114.3(6) ?
C20 N C9 . . 112.2(6) ?
C20 N C15 . . 112.5(6) ?
C9 N C15 . . 113.3(5) ?
O1 C18 H18A . . 109.5 ?
O1 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
O1 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
O2 C17 H17A . . 109.5 ?
O2 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
O2 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
O2 C3 C2 . . 124.0(6) ?
O2 C3 C4 . . 116.6(6) ?
C2 C3 C4 . . 119.2(6) ?
O1 C4 C12 . . 117.9(5) ?
O1 C4 C3 . . 120.5(6) ?
C12 C4 C3 . . 120.6(6) ?
C11 C12 C4 . . 118.8(5) ?
C11 C12 C13 . . 120.7(5) ?
C4 C12 C13 . . 119.9(5) ?
C12 C11 C1 . . 120.2(6) ?
C12 C11 C10 . . 122.0(5) ?
C1 C11 C10 . . 117.8(5) ?
C2 C1 C11 . . 122.1(6) ?
C2 C1 H1A . . 119.0 ?
C11 C1 H1A . . 119.0 ?
C1 C2 C3 . . 119.1(6) ?
C1 C2 H2A . . 120.5 ?
C3 C2 H2A . . 120.5 ?
O3 C19 H19A . . 109.5 ?
O3 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
O3 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
N C20 H20A . . 109.5 ?
N C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
N C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
N C15 C16 . . 112.4(5) ?
N C15 H15A . . 109.1 ?
C16 C15 H15A . . 109.1 ?
N C15 H15B . . 109.1 ?
C16 C15 H15B . . 109.1 ?
H15A C15 H15B . . 107.9 ?
C15 C16 C13 . . 110.4(5) ?
C15 C16 H16A . . 109.6 ?
C13 C16 H16A . . 109.6 ?
C15 C16 H16B . . 109.6 ?
C13 C16 H16B . . 109.6 ?
H16A C16 H16B . . 108.1 ?
C12 C13 C14 . . 111.0(5) ?
C12 C13 C5 . . 115.9(5) ?
C14 C13 C5 . . 103.5(4) ?
C12 C13 C16 . . 108.0(5) ?
C14 C13 C16 . . 106.8(5) ?
C5 C13 C16 . . 111.2(5) ?
C6 C5 C13 . . 112.7(5) ?
C6 C5 H5A . . 109.0 ?
C13 C5 H5A . . 109.0 ?
C6 C5 H5B . . 109.0 ?
C13 C5 H5B . . 109.0 ?
H5A C5 H5B . . 107.8 ?
O4 C6 C5 . . 124.2(6) ?
O4 C6 C7 . . 120.8(6) ?
C5 C6 C7 . . 115.0(5) ?
C8 C7 O3 . . 128.1(6) ?
C8 C7 C6 . . 119.7(6) ?
O3 C7 C6 . . 112.2(5) ?
C7 C8 C14 . . 122.8(6) ?
C7 C8 H8A . . 118.6 ?
C14 C8 H8A . . 118.6 ?
C8 C14 C9 . . 112.7(5) ?
C8 C14 C13 . . 114.8(5) ?
C9 C14 C13 . . 109.2(5) ?
C8 C14 H14A . . 106.5 ?
C9 C14 H14A . . 106.5 ?
C13 C14 H14A . . 106.5 ?
N C9 C10 . . 119.4(5) ?
N C9 C14 . . 108.8(5) ?
C10 C9 C14 . . 108.0(5) ?
N C9 H9A . . 106.7 ?
C10 C9 H9A . . 106.7 ?
C14 C9 H9A . . 106.7 ?
C9 C10 C11 . . 113.0(5) ?
C9 C10 H10A . . 109.0 ?
C11 C10 H10A . . 109.0 ?
C9 C10 H10B . . 109.0 ?
C11 C10 H10B . . 109.0 ?
H10A C10 H10B . . 107.8 ?
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 C18 . 1.278(11) ?
O1 C4 . 1.344(9) ?
O2 C3 . 1.360(8) ?
O2 C17 . 1.388(9) ?
O3 C7 . 1.377(8) ?
O3 C19 . 1.424(9) ?
O4 C6 . 1.217(8) ?
N C20 . 1.461(10) ?
N C9 . 1.466(9) ?
N C15 . 1.466(9) ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 0.9600 ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
C3 C2 . 1.386(10) ?
C3 C4 . 1.428(8) ?
C4 C12 . 1.385(9) ?
C12 C11 . 1.376(8) ?
C12 C13 . 1.524(7) ?
C11 C1 . 1.395(8) ?
C11 C10 . 1.531(9) ?
C1 C2 . 1.363(10) ?
C1 H1A . 0.9300 ?
C2 H2A . 0.9300 ?
C19 H19A . 0.9600 ?
C19 H19B . 0.9600 ?
C19 H19C . 0.9600 ?
C20 H20A . 0.9600 ?
C20 H20B . 0.9600 ?
C20 H20C . 0.9600 ?
C15 C16 . 1.520(7) ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
C16 C13 . 1.541(8) ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C13 C14 . 1.528(8) ?
C13 C5 . 1.540(9) ?
C5 C6 . 1.490(10) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C6 C7 . 1.507(9) ?
C7 C8 . 1.330(9) ?
C8 C14 . 1.491(9) ?
C8 H8A . 0.9300 ?
C14 C9 . 1.523(8) ?
C14 H14A . 0.9800 ?
C9 C10 . 1.516(9) ?
C9 H9A . 0.9800 ?
C10 H10A . 0.9700 ?
C10 H10B . 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
_geom_hbond_publ_flag
C5 H5A O1 . 0.9700 2.2300 2.853(9) 121.00 yes
C16 H16B O1 . 0.9700 2.5300 3.102(10) 118.00 yes
C18 H18B O2 . 0.9600 2.1400 2.812(16) 126.00 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
C17 O2 C3 C2 . . . . 1.2(12) ?
C17 O2 C3 C4 . . . . -173.7(7) ?
C18 O1 C4 C12 . . . . 127.8(8) ?
C18 O1 C4 C3 . . . . -64.2(11) ?
O2 C3 C4 O1 . . . . 11.0(10) ?
C2 C3 C4 O1 . . . . -164.1(7) ?
O2 C3 C4 C12 . . . . 178.7(6) ?
C2 C3 C4 C12 . . . . 3.6(9) ?
O1 C4 C12 C11 . . . . 162.8(6) ?
C3 C4 C12 C11 . . . . -5.2(9) ?
O1 C4 C12 C13 . . . . -8.4(9) ?
C3 C4 C12 C13 . . . . -176.4(6) ?
C4 C12 C11 C1 . . . . 4.2(9) ?
C13 C12 C11 C1 . . . . 175.3(6) ?
C4 C12 C11 C10 . . . . -176.7(6) ?
C13 C12 C11 C10 . . . . -5.6(9) ?
C12 C11 C1 C2 . . . . -1.5(10) ?
C10 C11 C1 C2 . . . . 179.3(6) ?
C11 C1 C2 C3 . . . . -0.2(10) ?
O2 C3 C2 C1 . . . . -175.6(7) ?
C4 C3 C2 C1 . . . . -0.8(10) ?
C20 N C15 C16 . . . . 177.7(6) ?
C9 N C15 C16 . . . . -53.7(7) ?
N C15 C16 C13 . . . . 53.3(6) ?
C11 C12 C13 C14 . . . . 23.7(7) ?
C4 C12 C13 C14 . . . . -165.3(5) ?
C11 C12 C13 C5 . . . . 141.4(6) ?
C4 C12 C13 C5 . . . . -47.6(8) ?
C11 C12 C13 C16 . . . . -93.2(6) ?
C4 C12 C13 C16 . . . . 77.8(7) ?
C15 C16 C13 C12 . . . . 62.0(6) ?
C15 C16 C13 C14 . . . . -57.5(6) ?
C15 C16 C13 C5 . . . . -169.8(5) ?
C12 C13 C5 C6 . . . . -59.6(7) ?
C14 C13 C5 C6 . . . . 62.2(6) ?
C16 C13 C5 C6 . . . . 176.6(5) ?
C13 C5 C6 O4 . . . . 139.7(7) ?
C13 C5 C6 C7 . . . . -43.8(7) ?
C19 O3 C7 C8 . . . . -1.0(11) ?
C19 O3 C7 C6 . . . . 177.5(6) ?
O4 C6 C7 C8 . . . . -172.3(7) ?
C5 C6 C7 C8 . . . . 11.0(8) ?
O4 C6 C7 O3 . . . . 9.1(9) ?
C5 C6 C7 O3 . . . . -167.6(6) ?
O3 C7 C8 C14 . . . . 177.1(6) ?
C6 C7 C8 C14 . . . . -1.3(9) ?
C7 C8 C14 C9 . . . . 150.3(6) ?
C7 C8 C14 C13 . . . . 24.5(9) ?
C12 C13 C14 C8 . . . . 73.0(6) ?
C5 C13 C14 C8 . . . . -52.0(6) ?
C16 C13 C14 C8 . . . . -169.4(5) ?
C12 C13 C14 C9 . . . . -54.6(6) ?
C5 C13 C14 C9 . . . . -179.6(5) ?
C16 C13 C14 C9 . . . . 62.9(6) ?
C20 N C9 C10 . . . . 62.0(8) ?
C15 N C9 C10 . . . . -66.7(7) ?
C20 N C9 C14 . . . . -173.6(5) ?
C15 N C9 C14 . . . . 57.7(6) ?
C8 C14 C9 N . . . . 168.2(5) ?
C13 C14 C9 N . . . . -63.0(6) ?
C8 C14 C9 C10 . . . . -61.0(7) ?
C13 C14 C9 C10 . . . . 67.9(7) ?
N C9 C10 C11 . . . . 76.5(7) ?
C14 C9 C10 C11 . . . . -48.2(7) ?
C12 C11 C10 C9 . . . . 18.3(9) ?
C1 C11 C10 C9 . . . . -162.5(6) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24741332
