#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/37/2013775.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_2013775
loop_
_publ_author_name
'Sonar, Vijayakumar N.'
'Parkin, Sean'
'Crooks, Peter A.'
_publ_section_title
;
 (Z)-2-(1H-Indol-3-ylmethylene)-1-azabicyclo[2.2.2]octan-3-one
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o6
_journal_page_last               o8
_journal_paper_doi               10.1107/S0108270103026076
_journal_volume                  60
_journal_year                    2004
_chemical_formula_moiety         'C16 H16 N2 O'
_chemical_formula_sum            'C16 H16 N2 O'
_chemical_formula_weight         252.31
_chemical_name_systematic
;
2-(1H-Indol-3-ylmethylene)-1-aza-bicyclo[2.2.2]octan-3-one
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_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                 108.26(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   6.1800(12)
_cell_length_b                   44.160(9)
_cell_length_c                   9.774(2)
_cell_measurement_reflns_used    22075
_cell_measurement_temperature    173.0(10)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     2533.1(10)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction        'DENZO--SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'XP in SHELXTL/PC (Sheldrick, 1995)'
_computing_publication_material
;
SHELXL97 (Sheldrick, 1997) and local procedures
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173.0(10)
_diffrn_detector_area_resol_mean 18
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       'ω scans at fixed χ = 55°'
_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  0.0380
_diffrn_reflns_av_sigmaI/netI    0.0529
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       56
_diffrn_reflns_limit_k_min       -56
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            28160
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.84
_diffrn_standards_decay_%        <1
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9958
_exptl_absorpt_correction_T_min  0.9793
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'broken lath'
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.05
_refine_diff_density_max         .209
_refine_diff_density_min         -.171
_refine_ls_extinction_coef       0.0035(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         2906
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.122
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0482
_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)+(0.0249P)²+0.9406P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0778
_refine_ls_wR_factor_ref         0.0804
_reflns_number_gt                2589
_reflns_number_total             2906
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fr1450.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               2013775
_cod_database_fobs_code          2013775
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
loop_
_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
_atom_site_type_symbol
N1A 1.0088(3) 0.47368(5) 0.2176(2) 0.0238(5) Uani d . 1 . . N
H1A 1.0967 0.4780 0.1647 0.029 Uiso calc R 1 . . H
C2A 0.8549(4) 0.49267(6) 0.2437(3) 0.0227(6) Uani d . 1 . . C
H2A 0.8256 0.5127 0.2073 0.027 Uiso calc R 1 . . H
C3A 0.7455(4) 0.47877(6) 0.3312(3) 0.0213(5) Uani d . 1 . . C
C4A 0.8415(4) 0.44854(6) 0.3583(3) 0.0213(6) Uani d . 1 . . C
C5A 0.8048(5) 0.42331(6) 0.4333(3) 0.0263(6) Uani d . 1 . . C
H5A 0.6937 0.4240 0.4819 0.032 Uiso calc R 1 . . H
C6A 0.9304(5) 0.39732(6) 0.4369(3) 0.0295(6) Uani d . 1 . . C
H6A 0.9050 0.3801 0.4881 0.035 Uiso calc R 1 . . H
C7A 1.0951(5) 0.39605(6) 0.3657(3) 0.0299(7) Uani d . 1 . . C
H7A 1.1795 0.3779 0.3694 0.036 Uiso calc R 1 . . H
C8A 1.1368(5) 0.42052(6) 0.2908(3) 0.0287(7) Uani d . 1 . . C
H8A 1.2500 0.4197 0.2439 0.034 Uiso calc R 1 . . H
C9A 1.0072(4) 0.44645(6) 0.2863(3) 0.0212(6) Uani d . 1 . . C
C10A 0.5802(4) 0.49145(6) 0.3896(3) 0.0213(6) Uani d . 1 . . C
H10A 0.5215 0.4780 0.4452 0.026 Uiso calc R 1 . . H
C11A 0.4963(4) 0.51992(6) 0.3765(3) 0.0229(6) Uani d . 1 . . C
N12A 0.5588(4) 0.54340(5) 0.2928(2) 0.0266(5) Uani d . 1 . . N
C13A 0.3466(5) 0.55629(6) 0.1910(3) 0.0283(6) Uani d . 1 . . C
H13A 0.2646 0.5403 0.1237 0.034 Uiso calc R 1 . . H
H13B 0.3867 0.5726 0.1337 0.034 Uiso calc R 1 . . H
C14A 0.1880(4) 0.56931(6) 0.2725(3) 0.0262(6) Uani d . 1 . . C
H14A 0.1640 0.5912 0.2527 0.031 Uiso calc R 1 . . H
H14B 0.0380 0.5591 0.2397 0.031 Uiso calc R 1 . . H
C15A 0.3004(4) 0.56405(6) 0.4339(3) 0.0239(6) Uani d . 1 . . C
H15A 0.2004 0.5714 0.4900 0.029 Uiso calc R 1 . . H
C16A 0.5310(5) 0.58051(6) 0.4811(3) 0.0305(7) Uani d . 1 . . C
H16A 0.6082 0.5773 0.5853 0.037 Uiso calc R 1 . . H
H16B 0.5082 0.6025 0.4633 0.037 Uiso calc R 1 . . H
C17A 0.6773(4) 0.56743(6) 0.3927(3) 0.0310(7) Uani d . 1 . . C
H17A 0.7183 0.5840 0.3370 0.037 Uiso calc R 1 . . H
H17B 0.8203 0.5591 0.4596 0.037 Uiso calc R 1 . . H
C18A 0.3453(4) 0.53046(6) 0.4561(3) 0.0230(6) Uani d . 1 . . C
O18A 0.2657(3) 0.51427(4) 0.5318(2) 0.0294(5) Uani d . 1 . . O
N1B -0.1388(4) 0.77477(5) 0.5250(2) 0.0298(5) Uani d . 1 . . N
H1B -0.2827 0.7717 0.4755 0.036 Uiso calc R 1 . . H
C2B 0.0299(5) 0.75371(6) 0.5504(3) 0.0272(6) Uani d . 1 . . C
H2B 0.0097 0.7334 0.5163 0.033 Uiso calc R 1 . . H
C3B 0.2351(4) 0.76607(6) 0.6330(3) 0.0258(6) Uani d . 1 . . C
C4B 0.1858(4) 0.79724(6) 0.6570(3) 0.0256(6) Uani d . 1 . . C
C5B 0.3192(5) 0.82162(6) 0.7272(3) 0.0337(7) Uani d . 1 . . C
H5B 0.4781 0.8192 0.7737 0.040 Uiso calc R 1 . . H
C6B 0.2161(6) 0.84929(7) 0.7280(3) 0.0388(8) Uani d . 1 . . C
H6B 0.3061 0.8661 0.7738 0.047 Uiso calc R 1 . . H
C7B -0.0180(5) 0.85313(7) 0.6627(3) 0.0397(8) Uani d . 1 . . C
H7B -0.0848 0.8723 0.6667 0.048 Uiso calc R 1 . . H
C8B -0.1541(5) 0.82947(6) 0.5924(3) 0.0335(7) Uani d . 1 . . C
H8B -0.3134 0.8320 0.5481 0.040 Uiso calc R 1 . . H
C9B -0.0489(5) 0.80175(6) 0.5890(3) 0.0282(6) Uani d . 1 . . C
C10B 0.4539(4) 0.75192(6) 0.6913(3) 0.0266(6) Uani d . 1 . . C
H10B 0.5715 0.7646 0.7487 0.032 Uiso calc R 1 . . H
C11B 0.5161(5) 0.72328(6) 0.6764(3) 0.0269(6) Uani d . 1 . . C
N12B 0.3649(4) 0.70066(5) 0.5899(3) 0.0313(6) Uani d . 1 . . N
C13B 0.3347(5) 0.67665(7) 0.6879(3) 0.0370(8) Uani d . 1 . . C
H13C 0.2332 0.6607 0.6307 0.044 Uiso calc R 1 . . H
H13D 0.2603 0.6854 0.7551 0.044 Uiso calc R 1 . . H
C14B 0.5646(5) 0.66224(7) 0.7755(3) 0.0364(7) Uani d . 1 . . C
H14C 0.5893 0.6648 0.8799 0.044 Uiso calc R 1 . . H
H14D 0.5634 0.6403 0.7544 0.044 Uiso calc R 1 . . H
C15B 0.7570(5) 0.67793(6) 0.7334(3) 0.0307(7) Uani d . 1 . . C
H15B 0.9093 0.6696 0.7900 0.037 Uiso calc R 1 . . H
C16B 0.7123(5) 0.67355(7) 0.5715(3) 0.0346(7) Uani d . 1 . . C
H16C 0.7144 0.6517 0.5490 0.042 Uiso calc R 1 . . H
H16D 0.8323 0.6838 0.5412 0.042 Uiso calc R 1 . . H
C17B 0.4751(5) 0.68730(7) 0.4899(3) 0.0384(8) Uani d . 1 . . C
H17C 0.4936 0.7031 0.4227 0.046 Uiso calc R 1 . . H
H17D 0.3757 0.6713 0.4322 0.046 Uiso calc R 1 . . H
C18B 0.7440(5) 0.71166(6) 0.7582(3) 0.0282(6) Uani d . 1 . . C
O18B 0.9001(3) 0.72689(5) 0.8357(2) 0.0362(5) Uani d . 1 . . O
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .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
_geom_angle_publ_flag
C2A N1A C9A 109.7(2) ?
C2A N1A H1A 125.2 ?
C9A N1A H1A 125.2 ?
N1A C2A C3A 110.5(2) ?
N1A C2A H2A 124.8 ?
C3A C2A H2A 124.8 ?
C2A C3A C10A 128.2(2) y
C2A C3A C4A 105.6(2) ?
C10A C3A C4A 126.1(2) ?
C5A C4A C9A 118.2(2) ?
C5A C4A C3A 135.1(2) ?
C9A C4A C3A 106.7(2) ?
C6A C5A C4A 119.7(3) ?
C6A C5A H5A 120.1 ?
C4A C5A H5A 120.1 ?
C5A C6A C7A 120.7(3) ?
C5A C6A H6A 119.6 ?
C7A C6A H6A 119.6 ?
C8A C7A C6A 121.3(3) ?
C8A C7A H7A 119.4 ?
C6A C7A H7A 119.4 ?
C7A C8A C9A 117.6(3) ?
C7A C8A H8A 121.2 ?
C9A C8A H8A 121.2 ?
N1A C9A C8A 130.0(2) ?
N1A C9A C4A 107.6(2) ?
C8A C9A C4A 122.5(2) ?
C11A C10A C3A 128.8(2) y
C11A C10A H10A 115.6 ?
C3A C10A H10A 115.6 ?
C10A C11A N12A 123.9(2) y
C10A C11A C18A 122.3(2) y
N12A C11A C18A 113.6(2) y
C11A N12A C17A 107.9(2) ?
C11A N12A C13A 108.5(2) ?
C17A N12A C13A 108.6(2) ?
N12A C13A C14A 111.3(2) ?
N12A C13A H13A 109.4 ?
C14A C13A H13A 109.4 ?
N12A C13A H13B 109.4 ?
C14A C13A H13B 109.4 ?
H13A C13A H13B 108.0 ?
C15A C14A C13A 108.5(2) ?
C15A C14A H14A 110.0 ?
C13A C14A H14A 110.0 ?
C15A C14A H14B 110.0 ?
C13A C14A H14B 110.0 ?
H14A C14A H14B 108.4 ?
C18A C15A C14A 107.5(2) ?
C18A C15A C16A 108.1(2) ?
C14A C15A C16A 108.5(2) ?
C18A C15A H15A 110.9 ?
C14A C15A H15A 110.9 ?
C16A C15A H15A 110.9 ?
C15A C16A C17A 107.8(2) ?
C15A C16A H16A 110.2 ?
C17A C16A H16A 110.2 ?
C15A C16A H16B 110.2 ?
C17A C16A H16B 110.2 ?
H16A C16A H16B 108.5 ?
N12A C17A C16A 112.6(2) y
N12A C17A H17A 109.1 ?
C16A C17A H17A 109.1 ?
N12A C17A H17B 109.1 ?
C16A C17A H17B 109.1 ?
H17A C17A H17B 107.8 ?
O18A C18A C11A 124.9(2) ?
O18A C18A C15A 124.3(2) ?
C11A C18A C15A 110.7(2) ?
C2B N1B C9B 109.3(2) ?
C2B N1B H1B 125.3 ?
C9B N1B H1B 125.3 ?
N1B C2B C3B 110.3(2) ?
N1B C2B H2B 124.9 ?
C3B C2B H2B 124.9 ?
C2B C3B C10B 129.5(3) y
C2B C3B C4B 105.6(2) ?
C10B C3B C4B 124.8(2) ?
C5B C4B C9B 119.0(3) ?
C5B C4B C3B 133.7(3) ?
C9B C4B C3B 107.3(2) ?
C6B C5B C4B 118.8(3) ?
C6B C5B H5B 120.6 ?
C4B C5B H5B 120.6 ?
C5B C6B C7B 121.3(3) ?
C5B C6B H6B 119.3 ?
C7B C6B H6B 119.3 ?
C8B C7B C6B 121.2(3) ?
C8B C7B H7B 119.4 ?
C6B C7B H7B 119.4 ?
C7B C8B C9B 117.5(3) ?
C7B C8B H8B 121.3 ?
C9B C8B H8B 121.3 ?
N1B C9B C8B 130.3(3) ?
N1B C9B C4B 107.5(2) ?
C8B C9B C4B 122.2(3) ?
C11B C10B C3B 129.3(3) y
C11B C10B H10B 115.4 ?
C3B C10B H10B 115.4 ?
C10B C11B N12B 124.0(2) y
C10B C11B C18B 121.7(3) y
N12B C11B C18B 114.1(2) y
C11B N12B C17B 108.4(2) ?
C11B N12B C13B 107.8(2) ?
C17B N12B C13B 108.7(2) ?
N12B C13B C14B 111.9(2) ?
N12B C13B H13C 109.2 ?
C14B C13B H13C 109.2 ?
N12B C13B H13D 109.2 ?
C14B C13B H13D 109.2 ?
H13C C13B H13D 107.9 ?
C15B C14B C13B 108.6(2) ?
C15B C14B H14C 110.0 ?
C13B C14B H14C 110.0 ?
C15B C14B H14D 110.0 ?
C13B C14B H14D 110.0 ?
H14C C14B H14D 108.3 ?
C18B C15B C16B 106.7(2) ?
C18B C15B C14B 108.4(2) ?
C16B C15B C14B 108.3(2) ?
C18B C15B H15B 111.1 ?
C16B C15B H15B 111.1 ?
C14B C15B H15B 111.1 ?
C15B C16B C17B 108.5(2) ?
C15B C16B H16C 110.0 ?
C17B C16B H16C 110.0 ?
C15B C16B H16D 110.0 ?
C17B C16B H16D 110.0 ?
H16C C16B H16D 108.4 ?
N12B C17B C16B 111.8(2) y
N12B C17B H17C 109.3 ?
C16B C17B H17C 109.3 ?
N12B C17B H17D 109.3 ?
C16B C17B H17D 109.3 ?
H17C C17B H17D 107.9 ?
O18B C18B C11B 125.2(3) ?
O18B C18B C15B 124.6(3) ?
C11B C18B C15B 110.2(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
N1A C2A . 1.351(3) ?
N1A C9A . 1.379(3) ?
N1A H1A . 0.8800 ?
C2A C3A . 1.388(4) y
C2A H2A . 0.9500 ?
C3A C10A . 1.431(4) y
C3A C4A . 1.451(3) ?
C4A C5A . 1.391(4) ?
C4A C9A . 1.415(3) ?
C5A C6A . 1.380(4) ?
C5A H5A . 0.9500 ?
C6A C7A . 1.402(4) ?
C6A H6A . 0.9500 ?
C7A C8A . 1.374(4) ?
C7A H7A . 0.9500 ?
C8A C9A . 1.390(4) ?
C8A H8A . 0.9500 ?
C10A C11A . 1.351(3) y
C10A H10A . 0.9500 ?
C11A N12A . 1.446(3) ?
C11A C18A . 1.466(4) y
N12A C17A . 1.472(4) ?
N12A C13A . 1.489(3) ?
C13A C14A . 1.554(4) ?
C13A H13A . 0.9900 ?
C13A H13B . 0.9900 ?
C14A C15A . 1.529(4) ?
C14A H14A . 0.9900 ?
C14A H14B . 0.9900 ?
C15A C18A . 1.512(3) ?
C15A C16A . 1.536(4) ?
C15A H15A . 1.0000 ?
C16A C17A . 1.545(4) ?
C16A H16A . 0.9900 ?
C16A H16B . 0.9900 ?
C17A H17A . 0.9900 ?
C17A H17B . 0.9900 ?
C18A O18A . 1.236(3) y
N1B C2B . 1.360(3) ?
N1B C9B . 1.379(3) ?
N1B H1B . 0.8800 ?
C2B C3B . 1.384(4) y
C2B H2B . 0.9500 ?
C3B C10B . 1.436(4) y
C3B C4B . 1.444(4) ?
C4B C5B . 1.399(4) ?
C4B C9B . 1.408(4) ?
C5B C6B . 1.379(4) ?
C5B H5B . 0.9500 ?
C6B C7B . 1.397(5) ?
C6B H6B . 0.9500 ?
C7B C8B . 1.382(4) ?
C7B H7B . 0.9500 ?
C8B C9B . 1.391(4) ?
C8B H8B . 0.9500 ?
C10B C11B . 1.343(4) y
C10B H10B . 0.9500 ?
C11B N12B . 1.446(4) ?
C11B C18B . 1.477(4) y
N12B C17B . 1.478(4) ?
N12B C13B . 1.479(4) ?
C13B C14B . 1.548(4) ?
C13B H13C . 0.9900 ?
C13B H13D . 0.9900 ?
C14B C15B . 1.539(4) ?
C14B H14C . 0.9900 ?
C14B H14D . 0.9900 ?
C15B C18B . 1.515(4) ?
C15B C16B . 1.531(4) ?
C15B H15B . 1.0000 ?
C16B C17B . 1.556(4) ?
C16B H16C . 0.9900 ?
C16B H16D . 0.9900 ?
C17B H17C . 0.9900 ?
C17B H17D . 0.9900 ?
C18B O18B . 1.224(3) y
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
N1A H1A O18A 2_664 0.88 1.94 2.812(3) 174.0
N1B H1B O18B 4_364 0.88 2.01 2.872(3) 166.4
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
_geom_torsion_publ_flag
C9A N1A C2A C3A 0.2(3) ?
N1A C2A C3A C10A 176.6(2) ?
N1A C2A C3A C4A -0.7(3) ?
C2A C3A C4A C5A -178.4(3) ?
C10A C3A C4A C5A 4.2(5) ?
C2A C3A C4A C9A 1.0(3) ?
C10A C3A C4A C9A -176.4(2) ?
C9A C4A C5A C6A 0.6(4) ?
C3A C4A C5A C6A 179.9(3) ?
C4A C5A C6A C7A 0.1(4) ?
C5A C6A C7A C8A 0.1(4) ?
C6A C7A C8A C9A -1.0(4) ?
C2A N1A C9A C8A -179.4(3) ?
C2A N1A C9A C4A 0.5(3) ?
C7A C8A C9A N1A -178.4(3) ?
C7A C8A C9A C4A 1.7(4) ?
C5A C4A C9A N1A 178.6(2) ?
C3A C4A C9A N1A -0.9(3) ?
C5A C4A C9A C8A -1.5(4) ?
C3A C4A C9A C8A 179.0(2) ?
C2A C3A C10A C11A -1.8(5) y
C4A C3A C10A C11A 175.0(3) ?
C3A C10A C11A N12A 2.0(4) ?
C3A C10A C11A C18A -173.1(3) ?
C10A C11A N12A C17A -115.5(3) ?
C18A C11A N12A C17A 60.0(3) ?
C10A C11A N12A C13A 127.0(3) ?
C18A C11A N12A C13A -57.4(3) ?
C11A N12A C13A C14A 58.4(3) ?
C17A N12A C13A C14A -58.6(3) ?
N12A C13A C14A C15A -1.1(3) ?
C13A C14A C15A C18A -56.3(3) ?
C13A C14A C15A C16A 60.3(3) ?
C18A C15A C16A C17A 56.9(3) ?
C14A C15A C16A C17A -59.3(3) ?
C11A N12A C17A C16A -57.5(3) ?
C13A N12A C17A C16A 59.9(3) ?
C15A C16A C17A N12A -0.7(3) ?
C10A C11A C18A O18A -6.3(4) y
N12A C11A C18A O18A 178.1(2) ?
C10A C11A C18A C15A 173.4(2) ?
N12A C11A C18A C15A -2.2(3) ?
C14A C15A C18A O18A -120.3(3) ?
C16A C15A C18A O18A 122.8(3) ?
C14A C15A C18A C11A 59.9(3) ?
C16A C15A C18A C11A -56.9(3) ?
C9B N1B C2B C3B 0.6(3) ?
N1B C2B C3B C10B 176.4(3) ?
N1B C2B C3B C4B -1.0(3) ?
C2B C3B C4B C5B -177.7(3) ?
C10B C3B C4B C5B 4.7(5) ?
C2B C3B C4B C9B 1.0(3) ?
C10B C3B C4B C9B -176.6(2) ?
C9B C4B C5B C6B 0.2(4) ?
C3B C4B C5B C6B 178.8(3) ?
C4B C5B C6B C7B 1.3(5) ?
C5B C6B C7B C8B -1.4(5) ?
C6B C7B C8B C9B -0.1(4) ?
C2B N1B C9B C8B 180.0(3) ?
C2B N1B C9B C4B 0.1(3) ?
C7B C8B C9B N1B -178.3(3) ?
C7B C8B C9B C4B 1.6(4) ?
C5B C4B C9B N1B 178.3(2) ?
C3B C4B C9B N1B -0.7(3) ?
C5B C4B C9B C8B -1.6(4) ?
C3B C4B C9B C8B 179.4(3) ?
C2B C3B C10B C11B 2.4(5) y
C4B C3B C10B C11B 179.4(3) ?
C3B C10B C11B N12B 2.1(5) ?
C3B C10B C11B C18B -172.9(3) ?
C10B C11B N12B C17B 127.4(3) ?
C18B C11B N12B C17B -57.3(3) ?
C10B C11B N12B C13B -115.1(3) ?
C18B C11B N12B C13B 60.2(3) ?
C11B N12B C13B C14B -58.1(3) ?
C17B N12B C13B C14B 59.1(3) ?
N12B C13B C14B C15B 0.6(3) ?
C13B C14B C15B C18B 56.0(3) ?
C13B C14B C15B C16B -59.4(3) ?
C18B C15B C16B C17B -58.0(3) ?
C14B C15B C16B C17B 58.6(3) ?
C11B N12B C17B C16B 57.0(3) ?
C13B N12B C17B C16B -59.9(3) ?
C15B C16B C17B N12B 0.6(3) ?
C10B C11B C18B O18B -6.2(4) y
N12B C11B C18B O18B 178.4(3) ?
C10B C11B C18B C15B 173.3(3) ?
N12B C11B C18B C15B -2.1(3) ?
C16B C15B C18B O18B -120.3(3) ?
C14B C15B C18B O18B 123.2(3) ?
C16B C15B C18B C11B 60.1(3) ?
C14B C15B C18B C11B -56.4(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21107515
