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#$Date: 2025-08-22 13:33:34 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301861 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/01/7150179.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_7150179
loop_
_publ_author_name
'Zhuang, Wei'
'Hazell, Rita G.'
'Jørgensen, Karl Anker'
_publ_section_title
;
 Enantioselective Friedel-Crafts type addition of indoles to
 nitro-olefins using a chiral hydrogen-bonding catalyst--synthesis of
 optically active tetrahydro-beta-carbolines.
;
_journal_issue                   14
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2566
_journal_page_last               2571
_journal_paper_doi               10.1039/b505220c
_journal_volume                  3
_journal_year                    2005
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C31 H25 Cl1 N2 O1'
_chemical_formula_sum            'C31 H25 Cl N2 O'
_chemical_formula_weight         476.98
_space_group_IT_number           144
_symmetry_cell_setting           trigonal
_symmetry_Int_Tables_number      144
_symmetry_space_group_name_Hall  'P 31'
_symmetry_space_group_name_H-M   'P 31'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2005-01-24T10:45:59-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            3
_cell_length_a                   10.0175(8)
_cell_length_b                   10.0175(8)
_cell_length_c                   21.2378(13)
_cell_measurement_reflns_used    1904
_cell_measurement_temperature    225(2)
_cell_measurement_theta_max      20.57
_cell_measurement_theta_min      2.35
_cell_measurement_wavelength     0.71073
_cell_volume                     1845.7(2)
_computing_cell_refinement       'SAINT+ (Bruker-Nonius, 2004)'
_computing_data_collection       'Apex2 (Bruker-Nonius, 2004)'
_computing_data_reduction        'SAINT+ (Bruker-Nonius, 2004)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      225(2)
_diffrn_detector_area_resol_mean 0.0833
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX2 CCD-based diffractometer'
_diffrn_measurement_method       φ-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_unetI/netI     0.0764
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            4167
_diffrn_reflns_reduction_process
;
Scaled and merged with SORTAV
R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        25.94
_diffrn_reflns_theta_max         25.94
_diffrn_reflns_theta_min         2.54
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.182
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             750
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.17
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.962
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         4167
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.961
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0387
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0414P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0805
_refine_ls_wR_factor_ref         0.0905
_reflns_number_gt                2774
_reflns_number_total             4167
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b505220c.txt
_cod_data_source_block           04jowz002_0m
_cod_database_code               7150179
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.25431(9) 0.14116(9) 0.31830(4) 0.0589(2) Uani 1 1 d . . .
O1 O 0.1377(3) 0.6688(3) 0.54004(11) 0.0887(9) Uani 1 1 d . . .
N1 N 0.4943(3) 1.2088(3) 0.49649(9) 0.0396(6) Uani 1 1 d . . .
N2 N 0.2920(3) 0.7922(3) 0.45745(10) 0.0406(6) Uani 1 1 d . . .
C1 C 0.4209(3) 1.2349(3) 0.39872(11) 0.0360(7) Uani 1 1 d . . .
C2 C 0.4026(3) 1.3197(3) 0.35015(12) 0.0402(7) Uani 1 1 d . . .
H2 H 0.3553 1.271 0.3121 0.048 Uiso 1 1 calc R . .
C3 C 0.4538(4) 1.4731(3) 0.35842(14) 0.0456(8) Uani 1 1 d . . .
H3 H 0.4414 1.5294 0.3258 0.055 Uiso 1 1 calc R . .
C4 C 0.5247(4) 1.5480(4) 0.41487(14) 0.0479(8) Uani 1 1 d . . .
H4 H 0.5599 1.6538 0.4194 0.057 Uiso 1 1 calc R . .
C5 C 0.5431(3) 1.4687(4) 0.46354(13) 0.0431(7) Uani 1 1 d . . .
H5 H 0.5903 1.5186 0.5014 0.052 Uiso 1 1 calc R . .
C6 C 0.4900(3) 1.3123(3) 0.45524(12) 0.0363(7) Uani 1 1 d . . .
C7 C 0.4293(3) 1.0674(3) 0.46656(12) 0.0373(7) Uani 1 1 d . . .
C8 C 0.3867(3) 1.0792(3) 0.40667(12) 0.0357(7) Uani 1 1 d . . .
C9 C 0.3195(3) 0.9468(3) 0.36117(12) 0.0376(7) Uani 1 1 d . . .
H9 H 0.3864 0.9809 0.3234 0.045 Uiso 1 1 calc R . .
C9A C 0.1588(3) 0.9020(3) 0.33923(12) 0.0391(7) Uani 1 1 d . . .
C9B C 0.0551(4) 0.9162(4) 0.37710(15) 0.0522(8) Uani 1 1 d . . .
H9B H 0.0842 0.9538 0.4183 0.063 Uiso 1 1 calc R . .
C9C C -0.0911(4) 0.8767(4) 0.35612(18) 0.0648(10) Uani 1 1 d . . .
H9C H -0.16 0.8868 0.3831 0.078 Uiso 1 1 calc R . .
C9D C -0.1349(5) 0.8234(4) 0.2965(2) 0.0781(12) Uani 1 1 d . . .
H9D H -0.2334 0.798 0.2819 0.094 Uiso 1 1 calc R . .
C9E C -0.0337(5) 0.8070(4) 0.25766(19) 0.0788(13) Uani 1 1 d . . .
H9E H -0.0641 0.769 0.2166 0.095 Uiso 1 1 calc R . .
C9F C 0.1122(4) 0.8460(4) 0.27873(15) 0.0579(9) Uani 1 1 d . . .
H9F H 0.1801 0.8344 0.2518 0.069 Uiso 1 1 calc R . .
C10 C 0.3317(3) 0.8130(3) 0.38998(12) 0.0409(7) Uani 1 1 d . . .
H10A H 0.2623 0.7178 0.3674 0.049 Uiso 1 1 calc R . .
H10B H 0.4371 0.8326 0.3846 0.049 Uiso 1 1 calc R . .
C11 C 0.4004(3) 0.9216(3) 0.49791(12) 0.0405(7) Uani 1 1 d . . .
H11 H 0.3471 0.9133 0.5382 0.049 Uiso 1 1 calc R . .
C11A C 0.5429(4) 0.9093(3) 0.51288(12) 0.0413(7) Uani 1 1 d . . .
C11B C 0.6888(4) 1.0179(4) 0.49245(14) 0.0546(9) Uani 1 1 d . . .
H11B H 0.7026 1.1013 0.4674 0.065 Uiso 1 1 calc R . .
C11C C 0.8144(4) 1.0029(5) 0.50918(16) 0.0671(10) Uani 1 1 d . . .
H11C H 0.9134 1.0767 0.4953 0.081 Uiso 1 1 calc R . .
C11D C 0.7963(5) 0.8822(5) 0.54552(16) 0.0677(11) Uani 1 1 d . . .
H11D H 0.8823 0.8733 0.5567 0.081 Uiso 1 1 calc R . .
C11E C 0.6518(5) 0.7743(4) 0.56553(15) 0.0612(10) Uani 1 1 d . . .
H11E H 0.6389 0.6911 0.5905 0.073 Uiso 1 1 calc R . .
C11F C 0.5249(4) 0.7870(4) 0.54932(13) 0.0510(8) Uani 1 1 d . . .
H11F H 0.4262 0.7122 0.5631 0.061 Uiso 1 1 calc R . .
C12 C 0.1659(4) 0.6729(4) 0.48344(14) 0.0535(9) Uani 1 1 d . . .
C13 C 0.0621(4) 0.5406(4) 0.44138(14) 0.0488(8) Uani 1 1 d . . .
C14 C -0.0759(4) 0.5257(4) 0.42095(14) 0.0526(8) Uani 1 1 d . . .
H14 H -0.1034 0.5992 0.4326 0.063 Uiso 1 1 calc R . .
C15 C -0.1734(4) 0.4022(4) 0.38324(15) 0.0516(8) Uani 1 1 d . . .
H15 H -0.2667 0.3922 0.3688 0.062 Uiso 1 1 calc R . .
C16 C -0.1328(4) 0.2937(3) 0.36690(13) 0.0457(8) Uani 1 1 d . . .
C17 C 0.0031(4) 0.3058(4) 0.38765(14) 0.0506(8) Uani 1 1 d . . .
H17 H 0.0296 0.231 0.3767 0.061 Uiso 1 1 calc R . .
C18 C 0.0999(4) 0.4306(4) 0.42493(14) 0.0526(8) Uani 1 1 d . . .
H18 H 0.1932 0.4404 0.4393 0.063 Uiso 1 1 calc R . .
C20 C 0.5663(4) 1.2486(4) 0.55832(13) 0.0542(9) Uani 1 1 d . . .
H20A H 0.5338 1.1553 0.5826 0.081 Uiso 1 1 calc R . .
H20B H 0.5355 1.3142 0.58 0.081 Uiso 1 1 calc R . .
H20C H 0.6775 1.3029 0.5536 0.081 Uiso 1 1 calc R . .
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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N1 C7 107.7(2) . . ?
C6 N1 C20 124.5(2) . . ?
C7 N1 C20 127.6(3) . . ?
C12 N2 C10 126.2(2) . . ?
C12 N2 C11 119.4(2) . . ?
C10 N2 C11 114.4(2) . . ?
C2 C1 C6 118.0(3) . . ?
C2 C1 C8 135.5(2) . . ?
C6 C1 C8 106.5(2) . . ?
C3 C2 C1 119.7(3) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 121.1(3) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 120.9(3) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 118.0(3) . . ?
C4 C5 H5 121 . . ?
C6 C5 H5 121 . . ?
N1 C6 C5 129.1(2) . . ?
N1 C6 C1 108.7(2) . . ?
C5 C6 C1 122.3(3) . . ?
C8 C7 N1 110.3(3) . . ?
C8 C7 C11 125.7(2) . . ?
N1 C7 C11 123.9(2) . . ?
C7 C8 C1 106.8(2) . . ?
C7 C8 C9 123.0(3) . . ?
C1 C8 C9 130.2(2) . . ?
C8 C9 C9A 113.7(2) . . ?
C8 C9 C10 108.6(2) . . ?
C9A C9 C10 113.7(2) . . ?
C8 C9 H9 106.8 . . ?
C9A C9 H9 106.8 . . ?
C10 C9 H9 106.8 . . ?
C9B C9A C9F 117.7(3) . . ?
C9B C9A C9 122.4(2) . . ?
C9F C9A C9 120.0(3) . . ?
C9A C9B C9C 121.8(3) . . ?
C9A C9B H9B 119.1 . . ?
C9C C9B H9B 119.1 . . ?
C9D C9C C9B 120.0(4) . . ?
C9D C9C H9C 120 . . ?
C9B C9C H9C 120 . . ?
C9C C9D C9E 119.5(4) . . ?
C9C C9D H9D 120.3 . . ?
C9E C9D H9D 120.3 . . ?
C9D C9E C9F 120.5(3) . . ?
C9D C9E H9E 119.7 . . ?
C9F C9E H9E 119.7 . . ?
C9E C9F C9A 120.6(4) . . ?
C9E C9F H9F 119.7 . . ?
C9A C9F H9F 119.7 . . ?
N2 C10 C9 112.2(2) . . ?
N2 C10 H10A 109.2 . . ?
C9 C10 H10A 109.2 . . ?
N2 C10 H10B 109.2 . . ?
C9 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
N2 C11 C7 107.2(2) . . ?
N2 C11 C11A 110.9(2) . . ?
C7 C11 C11A 116.0(2) . . ?
N2 C11 H11 107.5 . . ?
C7 C11 H11 107.5 . . ?
C11A C11 H11 107.5 . . ?
C11F C11A C11B 119.3(3) . . ?
C11F C11A C11 118.4(3) . . ?
C11B C11A C11 122.3(3) . . ?
C11A C11B C11C 119.6(3) . . ?
C11A C11B H11B 120.2 . . ?
C11C C11B H11B 120.2 . . ?
C11D C11C C11B 120.9(4) . . ?
C11D C11C H11C 119.5 . . ?
C11B C11C H11C 119.5 . . ?
C11C C11D C11E 119.5(3) . . ?
C11C C11D H11D 120.2 . . ?
C11E C11D H11D 120.2 . . ?
C11D C11E C11F 120.5(3) . . ?
C11D C11E H11E 119.8 . . ?
C11F C11E H11E 119.8 . . ?
C11E C11F C11A 120.2(3) . . ?
C11E C11F H11F 119.9 . . ?
C11A C11F H11F 119.9 . . ?
O1 C12 N2 121.8(3) . . ?
O1 C12 C13 120.3(3) . . ?
N2 C12 C13 117.8(3) . . ?
C18 C13 C14 119.6(3) . . ?
C18 C13 C12 120.7(3) . . ?
C14 C13 C12 119.7(3) . . ?
C13 C14 C15 119.9(3) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C16 C15 C14 119.6(3) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C17 C16 C15 121.1(3) . . ?
C17 C16 Cl1 119.6(3) . . ?
C15 C16 Cl1 119.2(3) . . ?
C16 C17 C18 118.5(3) . . ?
C16 C17 H17 120.7 . . ?
C18 C17 H17 120.7 . . ?
C13 C18 C17 121.3(3) . . ?
C13 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
N1 C20 H20A 109.5 . . ?
N1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C16 1.738(3) . ?
O1 C12 1.231(3) . ?
N1 C6 1.374(4) . ?
N1 C7 1.383(3) . ?
N1 C20 1.455(3) . ?
N2 C12 1.349(4) . ?
N2 C10 1.474(3) . ?
N2 C11 1.480(3) . ?
C1 C2 1.405(4) . ?
C1 C6 1.408(4) . ?
C1 C8 1.429(4) . ?
C2 C3 1.366(4) . ?
C2 H2 0.94 . ?
C3 C4 1.404(4) . ?
C3 H3 0.94 . ?
C4 C5 1.371(4) . ?
C4 H4 0.94 . ?
C5 C6 1.392(4) . ?
C5 H5 0.94 . ?
C7 C8 1.366(4) . ?
C7 C11 1.496(4) . ?
C8 C9 1.501(4) . ?
C9 C9A 1.512(4) . ?
C9 C10 1.533(4) . ?
C9 H9 0.99 . ?
C9A C9B 1.377(4) . ?
C9A C9F 1.386(4) . ?
C9B C9C 1.386(5) . ?
C9B H9B 0.94 . ?
C9C C9D 1.358(5) . ?
C9C H9C 0.94 . ?
C9D C9E 1.379(6) . ?
C9D H9D 0.94 . ?
C9E C9F 1.385(5) . ?
C9E H9E 0.94 . ?
C9F H9F 0.94 . ?
C10 H10A 0.98 . ?
C10 H10B 0.98 . ?
C11 C11A 1.527(4) . ?
C11 H11 0.99 . ?
C11A C11F 1.383(4) . ?
C11A C11B 1.385(4) . ?
C11B C11C 1.386(4) . ?
C11B H11B 0.94 . ?
C11C C11D 1.368(5) . ?
C11C H11C 0.94 . ?
C11D C11E 1.371(5) . ?
C11D H11D 0.94 . ?
C11E C11F 1.382(5) . ?
C11E H11E 0.94 . ?
C11F H11F 0.94 . ?
C12 C13 1.503(5) . ?
C13 C18 1.377(5) . ?
C13 C14 1.384(4) . ?
C14 C15 1.385(4) . ?
C14 H14 0.94 . ?
C15 C16 1.382(4) . ?
C15 H15 0.94 . ?
C16 C17 1.377(4) . ?
C17 C18 1.384(4) . ?
C17 H17 0.94 . ?
C18 H18 0.94 . ?
C20 H20A 0.97 . ?
C20 H20B 0.97 . ?
C20 H20C 0.97 . ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 1.1(4) . . . . ?
C8 C1 C2 C3 -178.3(3) . . . . ?
C1 C2 C3 C4 -0.1(4) . . . . ?
C2 C3 C4 C5 -0.6(5) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C7 N1 C6 C5 -179.2(3) . . . . ?
C20 N1 C6 C5 -3.5(5) . . . . ?
C7 N1 C6 C1 0.2(3) . . . . ?
C20 N1 C6 C1 175.9(3) . . . . ?
C4 C5 C6 N1 -179.7(3) . . . . ?
C4 C5 C6 C1 1.0(4) . . . . ?
C2 C1 C6 N1 178.9(2) . . . . ?
C8 C1 C6 N1 -1.5(3) . . . . ?
C2 C1 C6 C5 -1.6(4) . . . . ?
C8 C1 C6 C5 177.9(3) . . . . ?
C6 N1 C7 C8 1.3(3) . . . . ?
C20 N1 C7 C8 -174.3(3) . . . . ?
C6 N1 C7 C11 -174.5(3) . . . . ?
C20 N1 C7 C11 9.9(4) . . . . ?
N1 C7 C8 C1 -2.2(3) . . . . ?
C11 C7 C8 C1 173.5(3) . . . . ?
N1 C7 C8 C9 177.0(2) . . . . ?
C11 C7 C8 C9 -7.3(4) . . . . ?
C2 C1 C8 C7 -178.3(3) . . . . ?
C6 C1 C8 C7 2.3(3) . . . . ?
C2 C1 C8 C9 2.5(5) . . . . ?
C6 C1 C8 C9 -176.9(3) . . . . ?
C7 C8 C9 C9A 119.3(3) . . . . ?
C1 C8 C9 C9A -61.7(4) . . . . ?
C7 C8 C9 C10 -8.3(4) . . . . ?
C1 C8 C9 C10 170.7(3) . . . . ?
C8 C9 C9A C9B -32.2(4) . . . . ?
C10 C9 C9A C9B 92.7(3) . . . . ?
C8 C9 C9A C9F 147.0(3) . . . . ?
C10 C9 C9A C9F -88.1(3) . . . . ?
C9F C9A C9B C9C -0.1(4) . . . . ?
C9 C9A C9B C9C 179.1(3) . . . . ?
C9A C9B C9C C9D -0.5(5) . . . . ?
C9B C9C C9D C9E 1.0(6) . . . . ?
C9C C9D C9E C9F -0.8(6) . . . . ?
C9D C9E C9F C9A 0.1(6) . . . . ?
C9B C9A C9F C9E 0.4(5) . . . . ?
C9 C9A C9F C9E -178.9(3) . . . . ?
C12 N2 C10 C9 110.8(3) . . . . ?
C11 N2 C10 C9 -65.8(3) . . . . ?
C8 C9 C10 N2 42.1(3) . . . . ?
C9A C9 C10 N2 -85.5(3) . . . . ?
C12 N2 C11 C7 -130.5(3) . . . . ?
C10 N2 C11 C7 46.3(3) . . . . ?
C12 N2 C11 C11A 101.9(3) . . . . ?
C10 N2 C11 C11A -81.2(3) . . . . ?
C8 C7 C11 N2 -11.0(4) . . . . ?
N1 C7 C11 N2 164.1(2) . . . . ?
C8 C7 C11 C11A 113.5(3) . . . . ?
N1 C7 C11 C11A -71.4(3) . . . . ?
N2 C11 C11A C11F -66.0(3) . . . . ?
C7 C11 C11A C11F 171.4(2) . . . . ?
N2 C11 C11A C11B 115.5(3) . . . . ?
C7 C11 C11A C11B -7.1(4) . . . . ?
C11F C11A C11B C11C -0.5(4) . . . . ?
C11 C11A C11B C11C 178.1(3) . . . . ?
C11A C11B C11C C11D 0.1(5) . . . . ?
C11B C11C C11D C11E 0.2(5) . . . . ?
C11C C11D C11E C11F -0.1(5) . . . . ?
C11D C11E C11F C11A -0.3(5) . . . . ?
C11B C11A C11F C11E 0.6(4) . . . . ?
C11 C11A C11F C11E -178.0(3) . . . . ?
C10 N2 C12 O1 -176.1(3) . . . . ?
C11 N2 C12 O1 0.3(5) . . . . ?
C10 N2 C12 C13 6.1(4) . . . . ?
C11 N2 C12 C13 -177.5(3) . . . . ?
O1 C12 C13 C18 -98.8(4) . . . . ?
N2 C12 C13 C18 79.1(4) . . . . ?
O1 C12 C13 C14 78.7(4) . . . . ?
N2 C12 C13 C14 -103.5(3) . . . . ?
C18 C13 C14 C15 -1.2(4) . . . . ?
C12 C13 C14 C15 -178.7(3) . . . . ?
C13 C14 C15 C16 0.8(4) . . . . ?
C14 C15 C16 C17 0.2(4) . . . . ?
C14 C15 C16 Cl1 -178.8(2) . . . . ?
C15 C16 C17 C18 -0.7(4) . . . . ?
Cl1 C16 C17 C18 178.3(2) . . . . ?
C14 C13 C18 C17 0.7(5) . . . . ?
C12 C13 C18 C17 178.2(3) . . . . ?
C16 C17 C18 C13 0.2(4) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9365828
2 PubChem 11190746
