#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/76/2227694.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_2227694
loop_
_publ_author_name
'Natarajan, S.'
'Indumathi, P.'
'Reddy, B. Palakshi'
'Vijayakumar, V.'
'Lakshman, P. L. Nilantha'
_publ_section_title
;
 Ethyl
 2-methyl-5-oxo-4-(3,4,5-trimethoxyphenyl)-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate
;
_journal_coeditor_code           JH2183
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2240
_journal_paper_doi               10.1107/S1600536810030333
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C22 H27 N1 O6'
_chemical_formula_moiety         'C22 H27 N1 O6'
_chemical_formula_sum            'C22 H27 N O6'
_chemical_formula_weight         401.44
_chemical_name_systematic
;
Ethyl 2-methyl-5-oxo-4-(3,4,5-trimethoxyphenyl)-1,4,5,6,7,8-
hexahydroquinoline-3-carboxylate
;
_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                109.77(3)
_cell_angle_beta                 95.420(10)
_cell_angle_gamma                104.41(2)
_cell_formula_units_Z            2
_cell_length_a                   7.512(2)
_cell_length_b                   10.4020(10)
_cell_length_c                   14.568(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2
_cell_volume                     1017.4(4)
_computing_cell_refinement       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1996)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Nonius MACH3'
_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  0.0129
_diffrn_reflns_av_sigmaI/netI    0.0221
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4471
_diffrn_reflns_theta_full        24.97
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         2.14
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.9803
_exptl_absorpt_correction_T_min  0.9757
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.180
_refine_ls_extinction_coef       0.013(3)
_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   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         3574
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0429
_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)+(0.0609P)²+0.3979P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1165
_refine_ls_wR_factor_ref         0.1285
_reflns_number_gt                2653
_reflns_number_total             3574
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            jh2183.cif
_cod_data_source_block           I
_cod_original_formula_sum        'C22 H27 N1 O6'
_cod_database_code               2227694
_cod_database_fobs_code          2227694
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
C C22 0.4600(4) 0.2952(4) 0.0056(2) 0.0841(9) Uani d . 1 . .
H H22A 0.4922 0.3586 -0.0293 0.101 Uiso calc R 1 . .
H H22B 0.3534 0.2153 -0.0339 0.101 Uiso calc R 1 . .
H H22C 0.5642 0.2613 0.0178 0.101 Uiso calc R 1 . .
H H1N -0.286(4) -0.135(3) 0.2897(18) 0.061(7) Uiso d . 1 . .
O O4 0.68460(19) 0.35699(15) 0.22606(11) 0.0519(4) Uani d . 1 . .
O O3 0.36747(19) 0.26111(15) 0.50993(10) 0.0523(4) Uani d . 1 . .
N N1 -0.1712(2) -0.09684(18) 0.30488(13) 0.0405(4) Uani d . 1 . .
O O1 0.41288(19) -0.16053(16) 0.25103(12) 0.0588(4) Uani d . 1 . .
C C6 0.1238(2) -0.11864(19) 0.27165(13) 0.0323(4) Uani d . 1 . .
C C1 -0.0644(2) -0.17812(19) 0.25700(13) 0.0347(4) Uani d . 1 . .
C C8 0.0925(2) 0.09809(19) 0.40306(13) 0.0346(4) Uani d . 1 . .
C C9 -0.0944(2) 0.0320(2) 0.38398(14) 0.0356(4) Uani d . 1 . .
C C15 0.4536(2) 0.20151(19) 0.27900(14) 0.0371(4) Uani d . 1 . .
H H15 0.5452 0.1991 0.3256 0.044 Uiso calc R 1 . .
O O2 0.0990(2) 0.30115(19) 0.54511(14) 0.0765(6) Uani d . 1 . .
C C5 0.2404(3) -0.2085(2) 0.23209(15) 0.0407(5) Uani d . 1 . .
C C16 0.5036(3) 0.28065(19) 0.22121(15) 0.0388(4) Uani d . 1 . .
O O6 0.4166(2) 0.36880(18) 0.09651(13) 0.0659(5) Uani d . 1 . .
C C19 0.1316(3) 0.1295(2) 0.19881(14) 0.0393(4) Uani d . 1 . .
H H19 0.0068 0.0788 0.1914 0.047 Uiso calc R 1 . .
C C7 0.2165(2) 0.03861(18) 0.33288(13) 0.0330(4) Uani d . 1 . .
H H7 0.3332 0.0471 0.3740 0.040 Uiso calc R 1 . .
C C14 0.2679(2) 0.12545(18) 0.26814(13) 0.0332(4) Uani d . 1 . .
O O5 0.0588(2) 0.21801(19) 0.06860(13) 0.0656(5) Uani d . 1 . .
C C3 -0.0564(3) -0.3963(2) 0.12134(17) 0.0557(6) Uani d . 1 . .
H H3A -0.0602 -0.3578 0.0694 0.067 Uiso calc R 1 . .
H H3B -0.1143 -0.4991 0.0910 0.067 Uiso calc R 1 . .
C C18 0.1810(3) 0.2088(2) 0.14062(15) 0.0430(5) Uani d . 1 . .
C C17 0.3684(3) 0.2858(2) 0.15175(15) 0.0438(5) Uani d . 1 . .
C C11 0.1788(3) 0.2281(2) 0.49145(15) 0.0446(5) Uani d . 1 . .
C C2 -0.1646(3) -0.3315(2) 0.19699(16) 0.0448(5) Uani d . 1 . .
H H2A -0.2869 -0.3398 0.1631 0.054 Uiso calc R 1 . .
H H2B -0.1832 -0.3840 0.2408 0.054 Uiso calc R 1 . .
C C10 -0.2342(3) 0.0813(2) 0.44419(16) 0.0479(5) Uani d . 1 . .
H H10A -0.1986 0.0885 0.5112 0.058 Uiso calc R 1 . .
H H10B -0.3565 0.0135 0.4152 0.058 Uiso calc R 1 . .
H H10C -0.2366 0.1733 0.4445 0.058 Uiso calc R 1 . .
C C4 0.1457(3) -0.3643(2) 0.16960(18) 0.0539(6) Uani d . 1 . .
H H4A 0.1496 -0.4198 0.2111 0.065 Uiso calc R 1 . .
H H4B 0.2156 -0.3952 0.1179 0.065 Uiso calc R 1 . .
C C20 -0.1304(3) 0.1336(3) 0.04654(18) 0.0630(7) Uani d . 1 . .
H H20A -0.1993 0.1503 -0.0050 0.076 Uiso calc R 1 . .
H H20B -0.1835 0.1588 0.1051 0.076 Uiso calc R 1 . .
H H20C -0.1369 0.0342 0.0244 0.076 Uiso calc R 1 . .
C C21 0.8277(3) 0.3578(3) 0.29756(19) 0.0573(6) Uani d . 1 . .
H H21A 0.9466 0.4146 0.2935 0.069 Uiso calc R 1 . .
H H21B 0.8305 0.2616 0.2845 0.069 Uiso calc R 1 . .
H H21C 0.8025 0.3978 0.3630 0.069 Uiso calc R 1 . .
C C13 0.6642(3) 0.4322(3) 0.5930(2) 0.0768(8) Uani d . 1 . .
H H13A 0.7287 0.5156 0.6512 0.092 Uiso calc R 1 . .
H H13B 0.6768 0.4544 0.5347 0.092 Uiso calc R 1 . .
H H13C 0.7174 0.3564 0.5904 0.092 Uiso calc R 1 . .
C C12 0.4662(3) 0.3867(3) 0.59723(18) 0.0667(7) Uani d . 1 . .
H H12A 0.4530 0.3652 0.6565 0.080 Uiso calc R 1 . .
H H12B 0.4124 0.4635 0.6007 0.080 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
O6 C22 H22A . . 109.5 ?
O6 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
O6 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
C16 O4 C21 . . 117.61(16) ?
C11 O3 C12 . . 116.21(17) ?
C1 N1 C9 . . 122.70(16) ?
C1 N1 H1N . . 116.1(17) ?
C9 N1 H1N . . 120.6(17) ?
C1 C6 C5 . . 119.71(16) ?
C1 C6 C7 . . 121.31(16) ?
C5 C6 C7 . . 118.90(15) ?
C6 C1 N1 . . 119.52(17) ?
C6 C1 C2 . . 124.04(17) ?
N1 C1 C2 . . 116.30(16) ?
C9 C8 C11 . . 120.34(17) ?
C9 C8 C7 . . 120.86(17) ?
C11 C8 C7 . . 118.80(16) ?
C8 C9 N1 . . 119.58(17) ?
C8 C9 C10 . . 126.59(18) ?
N1 C9 C10 . . 113.77(16) ?
C16 C15 C14 . . 120.44(18) ?
C16 C15 H15 . . 119.8 ?
C14 C15 H15 . . 119.8 ?
O1 C5 C6 . . 121.43(18) ?
O1 C5 C4 . . 120.26(18) ?
C6 C5 C4 . . 118.29(16) ?
O4 C16 C15 . . 124.14(18) ?
O4 C16 C17 . . 115.44(17) ?
C15 C16 C17 . . 120.42(17) ?
C17 O6 C22 . . 113.52(19) ?
C18 C19 C14 . . 120.14(17) ?
C18 C19 H19 . . 119.9 ?
C14 C19 H19 . . 119.9 ?
C6 C7 C14 . . 112.18(15) ?
C6 C7 C8 . . 110.40(14) ?
C14 C7 C8 . . 111.39(14) ?
C6 C7 H7 . . 107.6 ?
C14 C7 H7 . . 107.6 ?
C8 C7 H7 . . 107.6 ?
C15 C14 C19 . . 119.66(17) ?
C15 C14 C7 . . 119.36(16) ?
C19 C14 C7 . . 120.98(16) ?
C18 O5 C20 . . 118.35(18) ?
C2 C3 C4 . . 110.79(18) ?
C2 C3 H3A . . 109.5 ?
C4 C3 H3A . . 109.5 ?
C2 C3 H3B . . 109.5 ?
C4 C3 H3B . . 109.5 ?
H3A C3 H3B . . 108.1 ?
O5 C18 C19 . . 125.06(18) ?
O5 C18 C17 . . 114.73(18) ?
C19 C18 C17 . . 120.20(18) ?
O6 C17 C16 . . 120.62(18) ?
O6 C17 C18 . . 120.21(18) ?
C16 C17 C18 . . 119.13(18) ?
O2 C11 O3 . . 121.13(19) ?
O2 C11 C8 . . 126.93(19) ?
O3 C11 C8 . . 111.93(16) ?
C1 C2 C3 . . 111.44(16) ?
C1 C2 H2A . . 109.3 ?
C3 C2 H2A . . 109.3 ?
C1 C2 H2B . . 109.3 ?
C3 C2 H2B . . 109.3 ?
H2A C2 H2B . . 108.0 ?
C9 C10 H10A . . 109.5 ?
C9 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C9 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C5 C4 C3 . . 113.84(18) ?
C5 C4 H4A . . 108.8 ?
C3 C4 H4A . . 108.8 ?
C5 C4 H4B . . 108.8 ?
C3 C4 H4B . . 108.8 ?
H4A C4 H4B . . 107.7 ?
O5 C20 H20A . . 109.5 ?
O5 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
O5 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
O4 C21 H21A . . 109.5 ?
O4 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
O4 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
C12 C13 H13A . . 109.5 ?
C12 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C12 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
O3 C12 C13 . . 110.0(2) ?
O3 C12 H12A . . 109.7 ?
C13 C12 H12A . . 109.7 ?
O3 C12 H12B . . 109.7 ?
C13 C12 H12B . . 109.7 ?
H12A C12 H12B . . 108.2 ?
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
C22 O6 . 1.402(3) ?
C22 H22A . 0.9600 ?
C22 H22B . 0.9600 ?
C22 H22C . 0.9600 ?
O4 C16 . 1.375(2) ?
O4 C21 . 1.421(3) ?
O3 C11 . 1.350(2) ?
O3 C12 . 1.446(3) ?
N1 C1 . 1.374(2) ?
N1 C9 . 1.379(3) ?
N1 H1N . 0.83(3) ?
O1 C5 . 1.234(2) ?
C6 C1 . 1.358(2) ?
C6 C5 . 1.453(3) ?
C6 C7 . 1.512(3) ?
C1 C2 . 1.486(3) ?
C8 C9 . 1.355(2) ?
C8 C11 . 1.461(3) ?
C8 C7 . 1.528(2) ?
C9 C10 . 1.508(3) ?
C15 C16 . 1.379(3) ?
C15 C14 . 1.386(2) ?
C15 H15 . 0.9300 ?
O2 C11 . 1.209(2) ?
C5 C4 . 1.505(3) ?
C16 C17 . 1.389(3) ?
O6 C17 . 1.376(2) ?
C19 C18 . 1.384(3) ?
C19 C14 . 1.387(3) ?
C19 H19 . 0.9300 ?
C7 C14 . 1.525(2) ?
C7 H7 . 0.9800 ?
O5 C18 . 1.372(2) ?
O5 C20 . 1.413(3) ?
C3 C2 . 1.506(3) ?
C3 C4 . 1.516(3) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C18 C17 . 1.399(3) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C20 H20A . 0.9600 ?
C20 H20B . 0.9600 ?
C20 H20C . 0.9600 ?
C21 H21A . 0.9600 ?
C21 H21B . 0.9600 ?
C21 H21C . 0.9600 ?
C13 C12 . 1.458(3) ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
C12 H12A . 0.9700 ?
C12 H12B . 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
C7 H7 O3 . 0.98 2.36 2.720(2) 101
N1 H1N O1 1_455 0.83(3) 2.21(3) 2.995(2) 160(3)
C2 H2B O4 1_445 0.97 2.55 3.340(3) 138
C10 H10B O1 1_455 0.96 2.59 3.429(3) 146
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 C6 C1 N1 . . . . 171.81(16) ?
C7 C6 C1 N1 . . . . -5.1(3) ?
C5 C6 C1 C2 . . . . -3.6(3) ?
C7 C6 C1 C2 . . . . 179.45(17) ?
C9 N1 C1 C6 . . . . -14.9(3) ?
C9 N1 C1 C2 . . . . 160.86(18) ?
C11 C8 C9 N1 . . . . -174.65(17) ?
C7 C8 C9 N1 . . . . 5.4(3) ?
C11 C8 C9 C10 . . . . 2.4(3) ?
C7 C8 C9 C10 . . . . -177.55(17) ?
C1 N1 C9 C8 . . . . 14.7(3) ?
C1 N1 C9 C10 . . . . -162.71(17) ?
C1 C6 C5 O1 . . . . -173.80(19) ?
C7 C6 C5 O1 . . . . 3.2(3) ?
C1 C6 C5 C4 . . . . 4.2(3) ?
C7 C6 C5 C4 . . . . -178.84(18) ?
C21 O4 C16 C15 . . . . -2.2(3) ?
C21 O4 C16 C17 . . . . 178.60(18) ?
C14 C15 C16 O4 . . . . -178.84(17) ?
C14 C15 C16 C17 . . . . 0.3(3) ?
C1 C6 C7 C14 . . . . -103.04(19) ?
C5 C6 C7 C14 . . . . 80.0(2) ?
C1 C6 C7 C8 . . . . 21.8(2) ?
C5 C6 C7 C8 . . . . -155.10(16) ?
C9 C8 C7 C6 . . . . -22.0(2) ?
C11 C8 C7 C6 . . . . 158.08(16) ?
C9 C8 C7 C14 . . . . 103.36(19) ?
C11 C8 C7 C14 . . . . -76.6(2) ?
C16 C15 C14 C19 . . . . -0.2(3) ?
C16 C15 C14 C7 . . . . 179.89(16) ?
C18 C19 C14 C15 . . . . 0.1(3) ?
C18 C19 C14 C7 . . . . -179.92(17) ?
C6 C7 C14 C15 . . . . -120.58(18) ?
C8 C7 C14 C15 . . . . 115.10(18) ?
C6 C7 C14 C19 . . . . 59.5(2) ?
C8 C7 C14 C19 . . . . -64.8(2) ?
C20 O5 C18 C19 . . . . -4.4(3) ?
C20 O5 C18 C17 . . . . 174.56(19) ?
C14 C19 C18 O5 . . . . 178.62(19) ?
C14 C19 C18 C17 . . . . -0.3(3) ?
C22 O6 C17 C16 . . . . 91.5(3) ?
C22 O6 C17 C18 . . . . -90.4(3) ?
O4 C16 C17 O6 . . . . -3.2(3) ?
C15 C16 C17 O6 . . . . 177.59(18) ?
O4 C16 C17 C18 . . . . 178.77(17) ?
C15 C16 C17 C18 . . . . -0.5(3) ?
O5 C18 C17 O6 . . . . 3.4(3) ?
C19 C18 C17 O6 . . . . -177.62(18) ?
O5 C18 C17 C16 . . . . -178.56(18) ?
C19 C18 C17 C16 . . . . 0.5(3) ?
C12 O3 C11 O2 . . . . 0.6(3) ?
C12 O3 C11 C8 . . . . -178.82(19) ?
C9 C8 C11 O2 . . . . -12.8(3) ?
C7 C8 C11 O2 . . . . 167.2(2) ?
C9 C8 C11 O3 . . . . 166.62(17) ?
C7 C8 C11 O3 . . . . -13.4(2) ?
C6 C1 C2 C3 . . . . -24.4(3) ?
N1 C1 C2 C3 . . . . 160.04(18) ?
C4 C3 C2 C1 . . . . 49.9(3) ?
O1 C5 C4 C3 . . . . -158.6(2) ?
C6 C5 C4 C3 . . . . 23.5(3) ?
C2 C3 C4 C5 . . . . -50.4(3) ?
C11 O3 C12 C13 . . . . -164.3(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2123809
