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#$Date: 2025-08-19 23:06:29 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301812 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/43/4024355.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_4024355
loop_
_publ_author_name
'Michal Szostak'
'Lei Yao'
'Jeffrey Aubé'
_publ_contact_author
; 
   Prof. Jeffrey Aubé 
   Department of Medicinal Chemistry
   School of Pharmacy
   University of Kansas 
   Malott Hall 
   1251 Wescoe Hall Dr, Rm 4070 
   Lawrence, KS  66045-7582  USA 
;
_publ_contact_author_email       jaube@ku.edu
_publ_contact_author_fax         1(785)8645326
_publ_contact_author_phone       1(785)8644496
_publ_section_title
;
Stability of Medium-Bridged Twisted Amides in Aqueous Solutions
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1869
_journal_page_last               1875
_journal_paper_doi               10.1021/jo802192v
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C18 H20 Br N O'
_chemical_formula_weight         346.26
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 113.591(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.010(4)
_cell_length_b                   10.186(2)
_cell_length_c                   18.010(4)
_cell_measurement_reflns_used    4320
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.72
_cell_measurement_theta_min      2.35
_cell_volume                     3027.8(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'ω scans'
_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  0.0464
_diffrn_reflns_av_sigmaI/netI    0.0603
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            25292
_diffrn_reflns_theta_full        30.01
_diffrn_reflns_theta_max         30.01
_diffrn_reflns_theta_min         1.23
_diffrn_standards_decay_%        -0.06
_diffrn_standards_number         140
_exptl_absorpt_coefficient_mu    2.714
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.382
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.056
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.115
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         8742
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.990
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0453
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0478P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0883
_refine_ls_wR_factor_ref         0.0946
_reflns_number_gt                6917
_reflns_number_total             8742
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo802192v_si_002_1.cif
_cod_data_source_block           03144f_(Compound_4)
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               4024355
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.04325(2) 0.27436(4) 0.66011(2) 0.02358(10) Uani 1 1 d . . .
O1 O 0.57841(14) 0.3836(2) 0.98467(14) 0.0210(5) Uani 1 1 d . . .
N1 N 0.48590(18) 0.2193(3) 0.95044(18) 0.0206(6) Uani 1 1 d . . .
C1 C 0.4001(2) 0.1899(3) 0.9351(2) 0.0225(7) Uani 1 1 d . . .
H1A H 0.3979 0.1452 0.9830 0.027 Uiso 1 1 calc R . .
H1B H 0.3772 0.1296 0.8882 0.027 Uiso 1 1 calc R . .
C2 C 0.3490(2) 0.3151(3) 0.9177(2) 0.0185(7) Uani 1 1 d . . .
H21 H 0.2910 0.2939 0.9019 0.022 Uiso 1 1 calc R . .
H22 H 0.3672 0.3732 0.9657 0.022 Uiso 1 1 calc R . .
C3 C 0.36249(19) 0.3791(3) 0.84837(19) 0.0139(6) Uani 1 1 d . . .
H3 H 0.3581 0.3068 0.8093 0.017 Uiso 1 1 calc R . .
C4 C 0.4494(2) 0.4278(3) 0.87826(19) 0.0158(6) Uani 1 1 d . . .
H4 H 0.4522 0.5218 0.8952 0.019 Uiso 1 1 calc R . .
C5 C 0.4763(2) 0.4151(3) 0.8076(2) 0.0184(7) Uani 1 1 d . . .
H5 H 0.5295 0.4610 0.8232 0.022 Uiso 1 1 calc R . .
C6 C 0.4871(2) 0.2697(4) 0.7862(2) 0.0211(7) Uani 1 1 d . . .
H6A H 0.4343 0.2246 0.7707 0.025 Uiso 1 1 calc R . .
H6B H 0.5003 0.2704 0.7379 0.025 Uiso 1 1 calc R . .
C7 C 0.5522(2) 0.1865(4) 0.8526(2) 0.0285(9) Uani 1 1 d . . .
H7A H 0.5675 0.1131 0.8256 0.034 Uiso 1 1 calc R . .
H7B H 0.6010 0.2419 0.8787 0.034 Uiso 1 1 calc R . .
C8 C 0.5302(2) 0.1284(3) 0.9197(2) 0.0272(8) Uani 1 1 d . . .
H8A H 0.4968 0.0489 0.8986 0.033 Uiso 1 1 calc R . .
H8B H 0.5807 0.1009 0.9653 0.033 Uiso 1 1 calc R . .
C9 C 0.5090(2) 0.3479(3) 0.9459(2) 0.0175(7) Uani 1 1 d . . .
C10 C 0.3075(2) 0.4904(3) 0.7973(2) 0.0172(7) Uani 1 1 d . . .
H10 H 0.3118 0.5677 0.8330 0.021 Uiso 1 1 calc R . .
C11 C 0.3415(2) 0.5274(3) 0.7349(2) 0.0170(7) Uani 1 1 d . . .
H11 H 0.3089 0.5809 0.6906 0.020 Uiso 1 1 calc R . .
C12 C 0.4133(2) 0.4902(3) 0.7381(2) 0.0205(7) Uani 1 1 d . . .
H12 H 0.4263 0.5123 0.6934 0.025 Uiso 1 1 calc R . .
C13 C 0.2202(2) 0.4454(3) 0.7594(2) 0.0159(7) Uani 1 1 d . . .
C14 C 0.1685(2) 0.4721(3) 0.7979(2) 0.0199(7) Uani 1 1 d . . .
H14 H 0.1873 0.5258 0.8449 0.024 Uiso 1 1 calc R . .
C15 C 0.0903(2) 0.4226(3) 0.7695(2) 0.0201(7) Uani 1 1 d . . .
H15 H 0.0558 0.4411 0.7967 0.024 Uiso 1 1 calc R . .
C16 C 0.0637(2) 0.3451(3) 0.7003(2) 0.0182(7) Uani 1 1 d . . .
C17 C 0.1119(2) 0.3199(3) 0.6583(2) 0.0179(7) Uani 1 1 d . . .
H17 H 0.0918 0.2699 0.6098 0.021 Uiso 1 1 calc R . .
C18 C 0.1905(2) 0.3696(3) 0.6889(2) 0.0175(7) Uani 1 1 d . . .
H18 H 0.2246 0.3515 0.6613 0.021 Uiso 1 1 calc R . .
Br2 Br 0.14622(2) 0.22432(4) -0.04699(2) 0.02203(9) Uani 1 1 d . . .
O2 O 0.46859(15) 0.0895(2) 0.57654(15) 0.0250(6) Uani 1 1 d . . .
N2 N 0.43743(17) 0.2630(3) 0.49043(18) 0.0178(6) Uani 1 1 d . . .
C21 C 0.4219(2) 0.3015(3) 0.4074(2) 0.0197(7) Uani 1 1 d . . .
H21A H 0.4706 0.3457 0.4065 0.024 Uiso 1 1 calc R . .
H21B H 0.3766 0.3650 0.3879 0.024 Uiso 1 1 calc R . .
C22 C 0.4008(2) 0.1826(3) 0.3499(2) 0.0184(7) Uani 1 1 d . . .
H22A H 0.3849 0.2109 0.2930 0.022 Uiso 1 1 calc R . .
H22B H 0.4473 0.1216 0.3647 0.022 Uiso 1 1 calc R . .
C23 C 0.32982(19) 0.1181(3) 0.36170(19) 0.0152(6) Uani 1 1 d . . .
H23 H 0.2929 0.1918 0.3611 0.018 Uiso 1 1 calc R . .
C24 C 0.3603(2) 0.0612(3) 0.44682(19) 0.0152(6) Uani 1 1 d . . .
H24 H 0.3748 -0.0333 0.4456 0.018 Uiso 1 1 calc R . .
C25 C 0.2904(2) 0.0732(3) 0.4748(2) 0.0178(7) Uani 1 1 d . . .
H25 H 0.3049 0.0199 0.5253 0.021 Uiso 1 1 calc R . .
C26 C 0.2740(2) 0.2170(3) 0.4947(2) 0.0196(7) Uani 1 1 d . . .
H26A H 0.2579 0.2693 0.4443 0.023 Uiso 1 1 calc R . .
H26B H 0.2270 0.2152 0.5100 0.023 Uiso 1 1 calc R . .
C27 C 0.3438(2) 0.2908(4) 0.5622(2) 0.0219(7) Uani 1 1 d . . .
H27A H 0.3196 0.3621 0.5825 0.026 Uiso 1 1 calc R . .
H27B H 0.3699 0.2289 0.6076 0.026 Uiso 1 1 calc R . .
C28 C 0.4107(2) 0.3514(3) 0.5402(2) 0.0222(8) Uani 1 1 d . . .
H28A H 0.3903 0.4342 0.5101 0.027 Uiso 1 1 calc R . .
H28B H 0.4578 0.3733 0.5908 0.027 Uiso 1 1 calc R . .
C29 C 0.4302(2) 0.1330(3) 0.5087(2) 0.0187(7) Uani 1 1 d . . .
C30 C 0.2752(2) 0.0144(3) 0.3039(2) 0.0181(7) Uani 1 1 d . . .
H30 H 0.3085 -0.0657 0.3071 0.022 Uiso 1 1 calc R . .
C31 C 0.2113(2) -0.0201(3) 0.3361(2) 0.0184(7) Uani 1 1 d . . .
H31 H 0.1647 -0.0669 0.3015 0.022 Uiso 1 1 calc R . .
C32 C 0.2170(2) 0.0115(3) 0.4105(2) 0.0190(7) Uani 1 1 d . . .
H32 H 0.1717 -0.0062 0.4233 0.023 Uiso 1 1 calc R . .
C33 C 0.2393(2) 0.0616(3) 0.2170(2) 0.0159(7) Uani 1 1 d . . .
C34 C 0.2803(2) 0.0351(3) 0.1683(2) 0.0213(7) Uani 1 1 d . . .
H34 H 0.3279 -0.0175 0.1888 0.026 Uiso 1 1 calc R . .
C35 C 0.2530(2) 0.0843(3) 0.0894(2) 0.0215(7) Uani 1 1 d . . .
H35 H 0.2819 0.0670 0.0564 0.026 Uiso 1 1 calc R . .
C36 C 0.1831(2) 0.1587(3) 0.0605(2) 0.0178(7) Uani 1 1 d . . .
C37 C 0.1399(2) 0.1851(3) 0.1071(2) 0.0174(7) Uani 1 1 d . . .
H37 H 0.0913 0.2348 0.0858 0.021 Uiso 1 1 calc R . .
C38 C 0.16899(19) 0.1376(3) 0.1857(2) 0.0157(7) Uani 1 1 d . . .
H38 H 0.1406 0.1571 0.2188 0.019 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 0.0000 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'
Br Br -0.2901 2.4595 '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
C9 N1 C8 110.6(3) . . ?
C9 N1 C1 119.5(3) . . ?
C8 N1 C1 119.0(3) . . ?
N1 C1 C2 111.5(3) . . ?
N1 C1 H1A 109.3 . . ?
C2 C1 H1A 109.3 . . ?
N1 C1 H1B 109.3 . . ?
C2 C1 H1B 109.3 . . ?
H1A C1 H1B 108.0 . . ?
C3 C2 C1 104.2(3) . . ?
C3 C2 H21 110.9 . . ?
C1 C2 H21 110.9 . . ?
C3 C2 H22 110.9 . . ?
C1 C2 H22 110.9 . . ?
H21 C2 H22 108.9 . . ?
C2 C3 C4 109.4(3) . . ?
C2 C3 C10 122.1(3) . . ?
C4 C3 C10 107.2(2) . . ?
C2 C3 H3 105.7 . . ?
C4 C3 H3 105.7 . . ?
C10 C3 H3 105.7 . . ?
C9 C4 C3 114.3(3) . . ?
C9 C4 C5 105.5(3) . . ?
C3 C4 C5 107.4(3) . . ?
C9 C4 H4 109.8 . . ?
C3 C4 H4 109.8 . . ?
C5 C4 H4 109.8 . . ?
C12 C5 C4 105.2(3) . . ?
C12 C5 C6 113.6(3) . . ?
C4 C5 C6 113.4(3) . . ?
C12 C5 H5 108.2 . . ?
C4 C5 H5 108.2 . . ?
C6 C5 H5 108.2 . . ?
C7 C6 C5 117.3(3) . . ?
C7 C6 H6A 108.0 . . ?
C5 C6 H6A 108.0 . . ?
C7 C6 H6B 108.0 . . ?
C5 C6 H6B 108.0 . . ?
H6A C6 H6B 107.2 . . ?
C8 C7 C6 117.7(3) . . ?
C8 C7 H7A 107.9 . . ?
C6 C7 H7A 107.9 . . ?
C8 C7 H7B 107.9 . . ?
C6 C7 H7B 107.9 . . ?
H7A C7 H7B 107.2 . . ?
N1 C8 C7 113.9(3) . . ?
N1 C8 H8A 108.8 . . ?
C7 C8 H8A 108.8 . . ?
N1 C8 H8B 108.8 . . ?
C7 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
O1 C9 N1 120.8(3) . . ?
O1 C9 C4 122.7(3) . . ?
N1 C9 C4 115.2(3) . . ?
C13 C10 C11 113.1(3) . . ?
C13 C10 C3 110.5(2) . . ?
C11 C10 C3 105.6(3) . . ?
C13 C10 H10 109.2 . . ?
C11 C10 H10 109.2 . . ?
C3 C10 H10 109.2 . . ?
C12 C11 C10 124.7(3) . . ?
C12 C11 H11 117.7 . . ?
C10 C11 H11 117.7 . . ?
C11 C12 C5 125.0(3) . . ?
C11 C12 H12 117.5 . . ?
C5 C12 H12 117.5 . . ?
C14 C13 C18 118.1(3) . . ?
C14 C13 C10 119.8(3) . . ?
C18 C13 C10 121.9(3) . . ?
C15 C14 C13 121.9(3) . . ?
C15 C14 H14 119.0 . . ?
C13 C14 H14 119.0 . . ?
C14 C15 C16 118.2(3) . . ?
C14 C15 H15 120.9 . . ?
C16 C15 H15 120.9 . . ?
C17 C16 C15 121.9(3) . . ?
C17 C16 Br1 118.8(3) . . ?
C15 C16 Br1 119.3(3) . . ?
C16 C17 C18 118.5(3) . . ?
C16 C17 H17 120.8 . . ?
C18 C17 H17 120.8 . . ?
C17 C18 C13 121.3(3) . . ?
C17 C18 H18 119.3 . . ?
C13 C18 H18 119.3 . . ?
C29 N2 C21 120.2(3) . . ?
C29 N2 C28 110.7(3) . . ?
C21 N2 C28 118.8(3) . . ?
N2 C21 C22 111.8(3) . . ?
N2 C21 H21A 109.3 . . ?
C22 C21 H21A 109.3 . . ?
N2 C21 H21B 109.3 . . ?
C22 C21 H21B 109.3 . . ?
H21A C21 H21B 107.9 . . ?
C23 C22 C21 103.9(3) . . ?
C23 C22 H22A 111.0 . . ?
C21 C22 H22A 111.0 . . ?
C23 C22 H22B 111.0 . . ?
C21 C22 H22B 111.0 . . ?
H22A C22 H22B 109.0 . . ?
C24 C23 C22 108.7(3) . . ?
C24 C23 C30 107.3(2) . . ?
C22 C23 C30 123.2(3) . . ?
C24 C23 H23 105.5 . . ?
C22 C23 H23 105.5 . . ?
C30 C23 H23 105.5 . . ?
C29 C24 C23 114.9(3) . . ?
C29 C24 C25 105.8(3) . . ?
C23 C24 C25 106.7(3) . . ?
C29 C24 H24 109.7 . . ?
C23 C24 H24 109.7 . . ?
C25 C24 H24 109.7 . . ?
C32 C25 C24 107.3(3) . . ?
C32 C25 C26 112.4(3) . . ?
C24 C25 C26 113.8(3) . . ?
C32 C25 H25 107.7 . . ?
C24 C25 H25 107.7 . . ?
C26 C25 H25 107.7 . . ?
C27 C26 C25 117.8(3) . . ?
C27 C26 H26A 107.9 . . ?
C25 C26 H26A 107.9 . . ?
C27 C26 H26B 107.9 . . ?
C25 C26 H26B 107.9 . . ?
H26A C26 H26B 107.2 . . ?
C28 C27 C26 117.8(3) . . ?
C28 C27 H27A 107.9 . . ?
C26 C27 H27A 107.9 . . ?
C28 C27 H27B 107.9 . . ?
C26 C27 H27B 107.9 . . ?
H27A C27 H27B 107.2 . . ?
N2 C28 C27 112.9(3) . . ?
N2 C28 H28A 109.0 . . ?
C27 C28 H28A 109.0 . . ?
N2 C28 H28B 109.0 . . ?
C27 C28 H28B 109.0 . . ?
H28A C28 H28B 107.8 . . ?
O2 C29 N2 121.1(3) . . ?
O2 C29 C24 122.6(3) . . ?
N2 C29 C24 114.9(3) . . ?
C33 C30 C31 113.1(3) . . ?
C33 C30 C23 112.1(3) . . ?
C31 C30 C23 106.1(3) . . ?
C33 C30 H30 108.5 . . ?
C31 C30 H30 108.5 . . ?
C23 C30 H30 108.5 . . ?
C32 C31 C30 123.9(3) . . ?
C32 C31 H31 118.0 . . ?
C30 C31 H31 118.0 . . ?
C31 C32 C25 124.2(3) . . ?
C31 C32 H32 117.9 . . ?
C25 C32 H32 117.9 . . ?
C34 C33 C38 118.7(3) . . ?
C34 C33 C30 118.6(3) . . ?
C38 C33 C30 122.5(3) . . ?
C33 C34 C35 121.0(3) . . ?
C33 C34 H34 119.5 . . ?
C35 C34 H34 119.5 . . ?
C36 C35 C34 118.4(3) . . ?
C36 C35 H35 120.8 . . ?
C34 C35 H35 120.8 . . ?
C35 C36 C37 122.0(3) . . ?
C35 C36 Br2 118.1(3) . . ?
C37 C36 Br2 119.9(3) . . ?
C36 C37 C38 118.6(3) . . ?
C36 C37 H37 120.7 . . ?
C38 C37 H37 120.7 . . ?
C37 C38 C33 121.2(3) . . ?
C37 C38 H38 119.4 . . ?
C33 C38 H38 119.4 . . ?
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
Br1 C16 1.907(3) . ?
O1 C9 1.218(4) . ?
N1 C9 1.387(4) . ?
N1 C8 1.468(4) . ?
N1 C1 1.487(5) . ?
C1 C2 1.530(5) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.512(4) . ?
C2 H21 0.9900 . ?
C2 H22 0.9900 . ?
C3 C4 1.520(4) . ?
C3 C10 1.544(4) . ?
C3 H3 1.0000 . ?
C4 C9 1.501(5) . ?
C4 C5 1.536(4) . ?
C4 H4 1.0000 . ?
C5 C12 1.519(5) . ?
C5 C6 1.562(5) . ?
C5 H5 1.0000 . ?
C6 C7 1.550(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.534(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C10 C13 1.513(5) . ?
C10 C11 1.527(4) . ?
C10 H10 1.0000 . ?
C11 C12 1.326(5) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.393(5) . ?
C13 C18 1.396(4) . ?
C14 C15 1.387(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.388(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.385(5) . ?
C17 C18 1.392(5) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
Br2 C36 1.900(3) . ?
O2 C29 1.220(4) . ?
N2 C29 1.383(4) . ?
N2 C21 1.461(5) . ?
N2 C28 1.481(4) . ?
C21 C22 1.539(5) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.526(4) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.521(4) . ?
C23 C30 1.532(4) . ?
C23 H23 1.0000 . ?
C24 C29 1.496(5) . ?
C24 C25 1.537(5) . ?
C24 H24 1.0000 . ?
C25 C32 1.502(5) . ?
C25 C26 1.564(5) . ?
C25 H25 1.0000 . ?
C26 C27 1.549(5) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.538(5) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C30 C33 1.512(5) . ?
C30 C31 1.523(5) . ?
C30 H30 1.0000 . ?
C31 C32 1.341(5) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C33 C34 1.381(5) . ?
C33 C38 1.397(4) . ?
C34 C35 1.398(5) . ?
C34 H34 0.9500 . ?
C35 C36 1.380(5) . ?
C35 H35 0.9500 . ?
C36 C37 1.380(5) . ?
C37 C38 1.384(5) . ?
C37 H37 0.9500 . ?
C38 H38 0.9500 . ?
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
C9 N1 C1 C2 -1.4(4) . . . . ?
C8 N1 C1 C2 -142.4(3) . . . . ?
N1 C1 C2 C3 54.7(4) . . . . ?
C1 C2 C3 C4 -68.7(3) . . . . ?
C1 C2 C3 C10 165.1(3) . . . . ?
C2 C3 C4 C9 30.5(4) . . . . ?
C10 C3 C4 C9 164.8(3) . . . . ?
C2 C3 C4 C5 147.1(3) . . . . ?
C10 C3 C4 C5 -78.6(3) . . . . ?
C9 C4 C5 C12 177.2(3) . . . . ?
C3 C4 C5 C12 54.9(3) . . . . ?
C9 C4 C5 C6 52.5(3) . . . . ?
C3 C4 C5 C6 -69.8(3) . . . . ?
C12 C5 C6 C7 178.0(3) . . . . ?
C4 C5 C6 C7 -62.0(4) . . . . ?
C5 C6 C7 C8 79.8(4) . . . . ?
C9 N1 C8 C7 -31.2(4) . . . . ?
C1 N1 C8 C7 113.0(3) . . . . ?
C6 C7 C8 N1 -42.2(5) . . . . ?
C8 N1 C9 O1 -63.1(4) . . . . ?
C1 N1 C9 O1 153.0(3) . . . . ?
C8 N1 C9 C4 104.1(3) . . . . ?
C1 N1 C9 C4 -39.8(4) . . . . ?
C3 C4 C9 O1 -169.1(3) . . . . ?
C5 C4 C9 O1 73.2(4) . . . . ?
C3 C4 C9 N1 24.0(4) . . . . ?
C5 C4 C9 N1 -93.7(3) . . . . ?
C2 C3 C10 C13 -57.6(4) . . . . ?
C4 C3 C10 C13 175.3(3) . . . . ?
C2 C3 C10 C11 179.8(3) . . . . ?
C4 C3 C10 C11 52.6(3) . . . . ?
C13 C10 C11 C12 -134.3(3) . . . . ?
C3 C10 C11 C12 -13.4(4) . . . . ?
C10 C11 C12 C5 -5.6(5) . . . . ?
C4 C5 C12 C11 -15.4(4) . . . . ?
C6 C5 C12 C11 109.2(4) . . . . ?
C11 C10 C13 C14 -146.9(3) . . . . ?
C3 C10 C13 C14 95.0(3) . . . . ?
C11 C10 C13 C18 37.5(4) . . . . ?
C3 C10 C13 C18 -80.7(4) . . . . ?
C18 C13 C14 C15 1.9(5) . . . . ?
C10 C13 C14 C15 -173.9(3) . . . . ?
C13 C14 C15 C16 -0.5(5) . . . . ?
C14 C15 C16 C17 -1.9(5) . . . . ?
C14 C15 C16 Br1 179.6(2) . . . . ?
C15 C16 C17 C18 2.8(5) . . . . ?
Br1 C16 C17 C18 -178.7(2) . . . . ?
C16 C17 C18 C13 -1.3(5) . . . . ?
C14 C13 C18 C17 -1.0(5) . . . . ?
C10 C13 C18 C17 174.7(3) . . . . ?
C29 N2 C21 C22 -1.6(4) . . . . ?
C28 N2 C21 C22 -143.5(3) . . . . ?
N2 C21 C22 C23 54.7(3) . . . . ?
C21 C22 C23 C24 -67.8(3) . . . . ?
C21 C22 C23 C30 165.7(3) . . . . ?
C22 C23 C24 C29 30.2(4) . . . . ?
C30 C23 C24 C29 165.4(3) . . . . ?
C22 C23 C24 C25 147.1(3) . . . . ?
C30 C23 C24 C25 -77.7(3) . . . . ?
C29 C24 C25 C32 175.5(2) . . . . ?
C23 C24 C25 C32 52.7(3) . . . . ?
C29 C24 C25 C26 50.6(4) . . . . ?
C23 C24 C25 C26 -72.3(3) . . . . ?
C32 C25 C26 C27 177.9(3) . . . . ?
C24 C25 C26 C27 -59.8(4) . . . . ?
C25 C26 C27 C28 79.8(4) . . . . ?
C29 N2 C28 C27 -30.7(4) . . . . ?
C21 N2 C28 C27 114.5(3) . . . . ?
C26 C27 C28 N2 -43.3(4) . . . . ?
C21 N2 C29 O2 153.4(3) . . . . ?
C28 N2 C29 O2 -62.0(4) . . . . ?
C21 N2 C29 C24 -39.7(4) . . . . ?
C28 N2 C29 C24 105.0(3) . . . . ?
C23 C24 C29 O2 -169.4(3) . . . . ?
C25 C24 C29 O2 73.1(4) . . . . ?
C23 C24 C29 N2 23.8(4) . . . . ?
C25 C24 C29 N2 -93.6(3) . . . . ?
C24 C23 C30 C33 178.5(3) . . . . ?
C22 C23 C30 C33 -54.3(4) . . . . ?
C24 C23 C30 C31 54.6(3) . . . . ?
C22 C23 C30 C31 -178.3(3) . . . . ?
C33 C30 C31 C32 -138.1(3) . . . . ?
C23 C30 C31 C32 -14.8(4) . . . . ?
C30 C31 C32 C25 -6.3(5) . . . . ?
C24 C25 C32 C31 -13.2(4) . . . . ?
C26 C25 C32 C31 112.6(4) . . . . ?
C31 C30 C33 C34 -148.3(3) . . . . ?
C23 C30 C33 C34 91.8(4) . . . . ?
C31 C30 C33 C38 35.7(4) . . . . ?
C23 C30 C33 C38 -84.3(4) . . . . ?
C38 C33 C34 C35 0.8(5) . . . . ?
C30 C33 C34 C35 -175.4(3) . . . . ?
C33 C34 C35 C36 -1.0(5) . . . . ?
C34 C35 C36 C37 -0.1(5) . . . . ?
C34 C35 C36 Br2 -179.7(2) . . . . ?
C35 C36 C37 C38 1.4(5) . . . . ?
Br2 C36 C37 C38 -179.0(2) . . . . ?
C36 C37 C38 C33 -1.7(5) . . . . ?
C34 C33 C38 C37 0.6(5) . . . . ?
C30 C33 C38 C37 176.6(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139091056
