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#$Date: 2025-08-20 11:41:31 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301828 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/33/4033353.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_4033353
loop_
_publ_author_name
'David R Chisholm'
'Garr-Layy Zhou'
'Ehmke Pohl'
'Roy Valentine'
'Andrew Whiting'
_publ_section_title
;
 Practical synthetic strategies towards lipophilic
 6-iodotetrahydroquinolines and -dihydroquinolines
;
_journal_name_full               'Beilstein Journal of Organic Chemistry'
_journal_page_first              1851
_journal_page_last               1862
_journal_paper_doi               10.3762/bjoc.12.174
_journal_volume                  12
_journal_year                    2016
_chemical_formula_moiety         'C12 H16 I N'
_chemical_formula_sum            'C12 H16 I N'
_chemical_formula_weight         301.16
_chemical_name_systematic
6-Iodo-4,4,8-trimethyl-1,2,3,4-tetrahydroquinoline
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 107.361(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.0060(8)
_cell_length_b                   9.8997(4)
_cell_length_c                   13.7872(6)
_cell_measurement_reflns_used    9973
_cell_measurement_temperature    120
_cell_measurement_theta_max      31.488
_cell_measurement_theta_min      2.575
_cell_volume                     2345.66(18)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      120
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            54918
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         31.571
_diffrn_reflns_theta_min         2.370
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.694
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9311
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.0462 before and 0.0371 after correction.
The Ratio of minimum to maximum transmission is 0.9311.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.706
_exptl_crystal_description       plate
_exptl_crystal_F_000             1184
_exptl_crystal_preparation       'Reduction of DC113'
_exptl_crystal_recrystallization_method
'The material was recrystallised from EtOAc by slow evaporation'
_exptl_crystal_size_max          0.266
_exptl_crystal_size_mid          0.165
_exptl_crystal_size_min          0.16
_refine_diff_density_max         1.717
_refine_diff_density_min         -2.798
_refine_diff_density_rms         0.109
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         7857
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0279
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0205P)²+3.5753P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0590
_refine_ls_wR_factor_ref         0.0632
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6697
_reflns_number_total             7857
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            14_1433619.cif
_cod_data_source_block           ho1
_cod_database_code               4033353
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C23(H23A,H23B), C24(H24A,H24B)
2.b Aromatic/amide H refined with riding coordinates:
 N8(H8), C3(H3), C5(H5), N22(H22), C17(H17), C19(H19)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C21(H21A,H21B,
 H21C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C)
;
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id DC29
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I14 I -0.02314(2) -0.08352(2) 0.23952(2) 0.02040(4) Uani 1 1 d . . . . .
N8 N 0.06720(10) 0.35960(17) -0.02987(13) 0.0181(3) Uani 1 1 d . . . . .
H8 H 0.0306 0.4151 -0.0644 0.022 Uiso 1 1 calc R . . . .
C1 C 0.04897(11) 0.25672(18) 0.02706(13) 0.0134(3) Uani 1 1 d . . . . .
C2 C 0.10732(10) 0.19266(18) 0.10500(13) 0.0127(3) Uani 1 1 d . . . . .
C3 C 0.08542(11) 0.09480(18) 0.16411(14) 0.0147(3) Uani 1 1 d . . . . .
H3 H 0.1241 0.0515 0.2173 0.018 Uiso 1 1 calc R . . . .
C4 C 0.00806(11) 0.06015(18) 0.14624(14) 0.0143(3) Uani 1 1 d . . . . .
C5 C -0.04928(11) 0.12079(19) 0.06815(14) 0.0150(3) Uani 1 1 d . . . . .
H5 H -0.1021 0.0946 0.0553 0.018 Uiso 1 1 calc R . . . .
C6 C -0.02972(10) 0.21958(18) 0.00881(13) 0.0139(3) Uani 1 1 d . . . . .
C7 C -0.09192(12) 0.2876(2) -0.07521(16) 0.0223(4) Uani 1 1 d . . . . .
H7A H -0.0914 0.3850 -0.0621 0.033 Uiso 1 1 calc GR . . . .
H7B H -0.1429 0.2505 -0.0778 0.033 Uiso 1 1 calc GR . . . .
H7C H -0.0819 0.2716 -0.1403 0.033 Uiso 1 1 calc GR . . . .
C9 C 0.14631(13) 0.3760(2) -0.03275(16) 0.0241(4) Uani 1 1 d . . . . .
H9A H 0.1527 0.4661 -0.0605 0.029 Uiso 1 1 calc R . . . .
H9B H 0.1585 0.3064 -0.0772 0.029 Uiso 1 1 calc R . . . .
C10 C 0.20090(12) 0.3622(2) 0.07435(16) 0.0222(4) Uani 1 1 d . . . . .
H10A H 0.1898 0.4353 0.1171 0.027 Uiso 1 1 calc R . . . .
H10B H 0.2552 0.3734 0.0728 0.027 Uiso 1 1 calc R . . . .
C11 C 0.19310(11) 0.22526(19) 0.12261(15) 0.0172(3) Uani 1 1 d . . . . .
C12 C 0.22931(14) 0.1132(2) 0.0744(2) 0.0332(5) Uani 1 1 d . . . . .
H12A H 0.2229 0.0261 0.1047 0.050 Uiso 1 1 calc GR . . . .
H12B H 0.2848 0.1317 0.0868 0.050 Uiso 1 1 calc GR . . . .
H12C H 0.2033 0.1104 0.0011 0.050 Uiso 1 1 calc GR . . . .
C13 C 0.23779(13) 0.2347(2) 0.23587(17) 0.0269(5) Uani 1 1 d . . . . .
H13A H 0.2115 0.2986 0.2689 0.040 Uiso 1 1 calc GR . . . .
H13B H 0.2909 0.2661 0.2439 0.040 Uiso 1 1 calc GR . . . .
H13C H 0.2396 0.1455 0.2673 0.040 Uiso 1 1 calc GR . . . .
I28 I 0.49778(2) 0.59738(2) 0.75627(2) 0.03775(5) Uani 1 1 d . . . . .
N22 N 0.57443(11) 0.15567(18) 0.47614(14) 0.0222(4) Uani 1 1 d . . . . .
H22 H 0.5365 0.1009 0.4441 0.027 Uiso 1 1 calc R . . . .
C15 C 0.55808(11) 0.25724(19) 0.53518(14) 0.0152(3) Uani 1 1 d . . . . .
C16 C 0.61881(11) 0.32284(18) 0.60920(13) 0.0138(3) Uani 1 1 d . . . . .
C17 C 0.60052(12) 0.42234(19) 0.66966(14) 0.0169(3) Uani 1 1 d . . . . .
H17 H 0.6410 0.4679 0.7191 0.020 Uiso 1 1 calc R . . . .
C18 C 0.52367(13) 0.4553(2) 0.65816(15) 0.0202(4) Uani 1 1 d . . . . .
C19 C 0.46394(12) 0.3918(2) 0.58537(16) 0.0223(4) Uani 1 1 d . . . . .
H19 H 0.4115 0.4166 0.5775 0.027 Uiso 1 1 calc R . . . .
C20 C 0.48018(11) 0.2924(2) 0.52392(15) 0.0188(4) Uani 1 1 d . . . . .
C21 C 0.41516(13) 0.2196(3) 0.44741(19) 0.0329(5) Uani 1 1 d . . . . .
H21A H 0.4205 0.2320 0.3793 0.049 Uiso 1 1 calc GR . . . .
H21B H 0.3651 0.2563 0.4493 0.049 Uiso 1 1 calc GR . . . .
H21C H 0.4176 0.1231 0.4638 0.049 Uiso 1 1 calc GR . . . .
C23 C 0.65088(15) 0.1347(3) 0.46430(19) 0.0306(5) Uani 1 1 d . . . . .
H23A H 0.6464 0.1314 0.3910 0.037 Uiso 1 1 calc R . . . .
H23B H 0.6716 0.0467 0.4947 0.037 Uiso 1 1 calc R . . . .
C24 C 0.70730(13) 0.2465(2) 0.51476(18) 0.0269(5) Uani 1 1 d . . . . .
H24A H 0.6955 0.3288 0.4721 0.032 Uiso 1 1 calc R . . . .
H24B H 0.7611 0.2181 0.5199 0.032 Uiso 1 1 calc R . . . .
C25 C 0.70195(11) 0.27930(19) 0.62150(15) 0.0170(3) Uani 1 1 d . . . . .
C26 C 0.76159(13) 0.3896(2) 0.66744(18) 0.0285(5) Uani 1 1 d . . . . .
H26A H 0.7482 0.4720 0.6265 0.043 Uiso 1 1 calc GR . . . .
H26B H 0.8135 0.3590 0.6682 0.043 Uiso 1 1 calc GR . . . .
H26C H 0.7613 0.4085 0.7371 0.043 Uiso 1 1 calc GR . . . .
C27 C 0.72108(14) 0.1545(2) 0.6901(2) 0.0318(5) Uani 1 1 d . . . . .
H27A H 0.7211 0.1790 0.7590 0.048 Uiso 1 1 calc GR . . . .
H27B H 0.7725 0.1201 0.6920 0.048 Uiso 1 1 calc GR . . . .
H27C H 0.6818 0.0845 0.6633 0.048 Uiso 1 1 calc GR . . . .
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'
I I -0.4742 1.8119 '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'
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
C1 N8 H8 120.0 . .
C1 N8 C9 120.05(17) . .
C9 N8 H8 120.0 . .
N8 C1 C2 120.97(17) . .
N8 C1 C6 119.07(17) . .
C2 C1 C6 119.92(16) . .
C1 C2 C11 121.02(16) . .
C3 C2 C1 118.74(16) . .
C3 C2 C11 120.20(16) . .
C2 C3 H3 119.6 . .
C4 C3 C2 120.85(17) . .
C4 C3 H3 119.6 . .
C3 C4 I14 119.82(14) . .
C3 C4 C5 120.52(17) . .
C5 C4 I14 119.66(14) . .
C4 C5 H5 119.9 . .
C6 C5 C4 120.15(17) . .
C6 C5 H5 119.9 . .
C1 C6 C7 119.75(17) . .
C5 C6 C1 119.78(17) . .
C5 C6 C7 120.46(17) . .
C6 C7 H7A 109.5 . .
C6 C7 H7B 109.5 . .
C6 C7 H7C 109.5 . .
H7A C7 H7B 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
N8 C9 H9A 109.9 . .
N8 C9 H9B 109.9 . .
N8 C9 C10 108.72(17) . .
H9A C9 H9B 108.3 . .
C10 C9 H9A 109.9 . .
C10 C9 H9B 109.9 . .
C9 C10 H10A 109.1 . .
C9 C10 H10B 109.1 . .
C9 C10 C11 112.66(17) . .
H10A C10 H10B 107.8 . .
C11 C10 H10A 109.1 . .
C11 C10 H10B 109.1 . .
C2 C11 C10 109.71(16) . .
C2 C11 C12 108.61(16) . .
C2 C11 C13 111.99(16) . .
C12 C11 C10 110.19(18) . .
C13 C11 C10 107.44(17) . .
C13 C11 C12 108.89(19) . .
C11 C12 H12A 109.5 . .
C11 C12 H12B 109.5 . .
C11 C12 H12C 109.5 . .
H12A C12 H12B 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C11 C13 H13A 109.5 . .
C11 C13 H13B 109.5 . .
C11 C13 H13C 109.5 . .
H13A C13 H13B 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C15 N22 H22 118.4 . .
C15 N22 C23 123.24(17) . .
C23 N22 H22 118.4 . .
N22 C15 C16 120.41(17) . .
N22 C15 C20 119.73(18) . .
C20 C15 C16 119.83(17) . .
C15 C16 C25 118.39(16) . .
C17 C16 C15 119.19(17) . .
C17 C16 C25 122.40(17) . .
C16 C17 H17 119.8 . .
C18 C17 C16 120.35(19) . .
C18 C17 H17 119.8 . .
C17 C18 I28 119.41(16) . .
C19 C18 I28 119.87(15) . .
C19 C18 C17 120.68(18) . .
C18 C19 H19 119.8 . .
C18 C19 C20 120.40(18) . .
C20 C19 H19 119.8 . .
C15 C20 C21 120.0(2) . .
C19 C20 C15 119.54(18) . .
C19 C20 C21 120.44(19) . .
C20 C21 H21A 109.5 . .
C20 C21 H21B 109.5 . .
C20 C21 H21C 109.5 . .
H21A C21 H21B 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
N22 C23 H23A 109.3 . .
N22 C23 H23B 109.3 . .
N22 C23 C24 111.79(18) . .
H23A C23 H23B 107.9 . .
C24 C23 H23A 109.3 . .
C24 C23 H23B 109.3 . .
C23 C24 H24A 109.3 . .
C23 C24 H24B 109.3 . .
C23 C24 C25 111.52(18) . .
H24A C24 H24B 108.0 . .
C25 C24 H24A 109.3 . .
C25 C24 H24B 109.3 . .
C16 C25 C24 107.12(16) . .
C16 C25 C26 112.99(17) . .
C16 C25 C27 109.30(16) . .
C26 C25 C24 108.08(17) . .
C26 C25 C27 108.63(18) . .
C27 C25 C24 110.72(18) . .
C25 C26 H26A 109.5 . .
C25 C26 H26B 109.5 . .
C25 C26 H26C 109.5 . .
H26A C26 H26B 109.5 . .
H26A C26 H26C 109.5 . .
H26B C26 H26C 109.5 . .
C25 C27 H27A 109.5 . .
C25 C27 H27B 109.5 . .
C25 C27 H27C 109.5 . .
H27A C27 H27B 109.5 . .
H27A C27 H27C 109.5 . .
H27B C27 H27C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I14 C4 2.1032(18) .
N8 H8 0.8800 .
N8 C1 1.384(2) .
N8 C9 1.446(3) .
C1 C2 1.410(2) .
C1 C6 1.412(3) .
C2 C3 1.396(2) .
C2 C11 1.525(3) .
C3 H3 0.9500 .
C3 C4 1.383(3) .
C4 C5 1.386(3) .
C5 H5 0.9500 .
C5 C6 1.386(3) .
C6 C7 1.508(3) .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C9 C10 1.516(3) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C10 C11 1.535(3) .
C11 C12 1.534(3) .
C11 C13 1.531(3) .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
I28 C18 2.098(2) .
N22 H22 0.8800 .
N22 C15 1.380(2) .
N22 C23 1.449(3) .
C15 C16 1.412(3) .
C15 C20 1.408(3) .
C16 C17 1.392(3) .
C16 C25 1.518(3) .
C17 H17 0.9500 .
C17 C18 1.384(3) .
C18 C19 1.384(3) .
C19 H19 0.9500 .
C19 C20 1.386(3) .
C20 C21 1.505(3) .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
C23 H23A 0.9900 .
C23 H23B 0.9900 .
C23 C24 1.523(3) .
C24 H24A 0.9900 .
C24 H24B 0.9900 .
C24 C25 1.538(3) .
C25 C26 1.530(3) .
C25 C27 1.532(3) .
C26 H26A 0.9800 .
C26 H26B 0.9800 .
C26 H26C 0.9800 .
C27 H27A 0.9800 .
C27 H27B 0.9800 .
C27 H27C 0.9800 .
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
I14 C4 C5 C6 177.38(13) . . . .
N8 C1 C2 C3 176.36(17) . . . .
N8 C1 C2 C11 -5.8(3) . . . .
N8 C1 C6 C5 -177.20(17) . . . .
N8 C1 C6 C7 2.9(3) . . . .
N8 C9 C10 C11 58.8(2) . . . .
C1 N8 C9 C10 -44.5(3) . . . .
C1 C2 C3 C4 0.6(3) . . . .
C1 C2 C11 C10 20.1(2) . . . .
C1 C2 C11 C12 -100.4(2) . . . .
C1 C2 C11 C13 139.27(18) . . . .
C2 C1 C6 C5 0.4(3) . . . .
C2 C1 C6 C7 -179.52(17) . . . .
C2 C3 C4 I14 -178.20(13) . . . .
C2 C3 C4 C5 0.9(3) . . . .
C3 C2 C11 C10 -162.12(17) . . . .
C3 C2 C11 C12 77.4(2) . . . .
C3 C2 C11 C13 -42.9(2) . . . .
C3 C4 C5 C6 -1.7(3) . . . .
C4 C5 C6 C1 1.0(3) . . . .
C4 C5 C6 C7 -179.02(17) . . . .
C6 C1 C2 C3 -1.2(3) . . . .
C6 C1 C2 C11 176.62(16) . . . .
C9 N8 C1 C2 18.8(3) . . . .
C9 N8 C1 C6 -163.55(18) . . . .
C9 C10 C11 C2 -46.5(2) . . . .
C9 C10 C11 C12 73.0(2) . . . .
C9 C10 C11 C13 -168.52(18) . . . .
C11 C2 C3 C4 -177.29(17) . . . .
I28 C18 C19 C20 -176.38(15) . . . .
N22 C15 C16 C17 -178.20(17) . . . .
N22 C15 C16 C25 0.3(3) . . . .
N22 C15 C20 C19 178.18(18) . . . .
N22 C15 C20 C21 -0.3(3) . . . .
N22 C23 C24 C25 45.3(3) . . . .
C15 N22 C23 C24 -6.3(3) . . . .
C15 C16 C17 C18 0.8(3) . . . .
C15 C16 C25 C24 36.8(2) . . . .
C15 C16 C25 C26 155.76(18) . . . .
C15 C16 C25 C27 -83.2(2) . . . .
C16 C15 C20 C19 0.4(3) . . . .
C16 C15 C20 C21 -178.04(19) . . . .
C16 C17 C18 I28 176.36(14) . . . .
C16 C17 C18 C19 -1.2(3) . . . .
C17 C16 C25 C24 -144.68(18) . . . .
C17 C16 C25 C26 -25.8(3) . . . .
C17 C16 C25 C27 95.3(2) . . . .
C17 C18 C19 C20 1.1(3) . . . .
C18 C19 C20 C15 -0.7(3) . . . .
C18 C19 C20 C21 177.7(2) . . . .
C20 C15 C16 C17 -0.4(3) . . . .
C20 C15 C16 C25 178.09(17) . . . .
C23 N22 C15 C16 -17.7(3) . . . .
C23 N22 C15 C20 164.5(2) . . . .
C23 C24 C25 C16 -59.3(2) . . . .
C23 C24 C25 C26 178.67(19) . . . .
C23 C24 C25 C27 59.8(2) . . . .
C25 C16 C17 C18 -177.65(17) . . . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139095888
