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#$Date: 2024-08-05 22:59:28 +0300 (Mon, 05 Aug 2024) $
#$Revision: 293937 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/99/7159985.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_7159985
loop_
_publ_author_name
'Mamale, Ajay G.'
'Paul, Sayantan'
'Gonnade, Rajesh G.'
'Bhattacharya, Asish K.'
_publ_section_title
;
 1,6-Conjugate addition of in situ generated aryldiazenes to
 p-quinone methides.
;
_journal_issue                   27
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5636
_journal_page_last               5645
_journal_paper_doi               10.1039/d4ob00618f
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C28 H33 Br N2 O'
_chemical_formula_sum            'C28 H33 Br N2 O'
_chemical_formula_weight         493.47
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   'difference Fourier'
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-08-17 deposited with the CCDC.	2024-06-14 downloaded from the CCDC.
;
_cell_angle_alpha                104.0870(10)
_cell_angle_beta                 108.9840(10)
_cell_angle_gamma                90.413(2)
_cell_formula_units_Z            2
_cell_length_a                   10.0089(4)
_cell_length_b                   11.1233(5)
_cell_length_c                   12.0576(5)
_cell_measurement_reflns_used    9890
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.75
_cell_measurement_theta_min      2.16
_cell_volume                     1225.74(9)
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL, Mercury 2020.20'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            34833
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.787
_diffrn_reflns_theta_min         2.279
_diffrn_source                   'micro-focus sealed tube'
_diffrn_source_type              'Incoatech I\mS HB'
_exptl_absorpt_coefficient_mu    1.699
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6269
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_description       plate
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.524
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         6362
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0263
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0288P)²+0.5404P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0673
_refine_ls_wR_factor_ref         0.0689
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5760
_reflns_number_total             6362
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob00618f2.cif
_cod_data_source_block           mo_AR_5_AAA_0m_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_atom_sites_solution_primary' value 'direct method' was
changed to 'direct'.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7159985--7159987.cif.
;
_cod_database_code               7159985
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_min   0.797
_shelx_estimated_absorpt_t_max   0.876
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
Br1 Br -0.12016(2) 0.11810(2) 0.33883(2) 0.02417(5) Uani 1 1 d . . . . .
O1 O 0.88409(10) 0.25309(9) 0.97471(9) 0.01627(19) Uani 1 1 d . . . . .
H1 H 0.862(2) 0.240(2) 1.021(2) 0.035(6) Uiso 1 1 d . . . . .
N1 N 0.45666(11) 0.54410(10) 0.62565(9) 0.0133(2) Uani 1 1 d . . . . .
N2 N 0.57610(12) 0.62168(10) 0.69024(10) 0.0150(2) Uani 1 1 d . . . . .
H1N H 0.6413(19) 0.6010(17) 0.7473(17) 0.022 Uiso 1 1 d . U . . .
C1 C 0.44753(13) 0.43456(12) 0.64354(11) 0.0124(2) Uani 1 1 d . . . . .
C2 C 0.57876(13) 0.74563(12) 0.68490(11) 0.0130(2) Uani 1 1 d . . . . .
C3 C 0.46191(14) 0.79055(12) 0.61144(12) 0.0161(2) Uani 1 1 d . . . . .
H3 H 0.377765 0.736842 0.565099 0.019 Uiso 1 1 calc R U . . .
C4 C 0.46869(15) 0.91363(13) 0.60615(13) 0.0192(3) Uani 1 1 d . . . . .
H4 H 0.389175 0.943456 0.555513 0.023 Uiso 1 1 calc R U . . .
C5 C 0.59032(15) 0.99352(13) 0.67400(13) 0.0196(3) Uani 1 1 d . . . . .
H5 H 0.594913 1.077616 0.669967 0.023 Uiso 1 1 calc R U . . .
C6 C 0.70544(14) 0.94837(13) 0.74803(12) 0.0179(3) Uani 1 1 d . . . . .
H6 H 0.788516 1.003140 0.795242 0.021 Uiso 1 1 calc R U . . .
C7 C 0.70262(13) 0.82552(12) 0.75503(11) 0.0145(2) Uani 1 1 d . . . . .
C8 C 0.82955(14) 0.77977(14) 0.83582(13) 0.0201(3) Uani 1 1 d . . . . .
H8A H 0.860202 0.708453 0.787272 0.030 Uiso 1 1 calc R U . . .
H8B H 0.803997 0.754359 0.899196 0.030 Uiso 1 1 calc R U . . .
H8C H 0.907049 0.846714 0.873578 0.030 Uiso 1 1 calc R U . . .
C9 C 0.56175(13) 0.38581(11) 0.73154(11) 0.0120(2) Uani 1 1 d . . . . .
C10 C 0.69632(13) 0.37655(11) 0.72112(11) 0.0121(2) Uani 1 1 d . . . . .
H10 H 0.713921 0.401232 0.656666 0.015 Uiso 1 1 calc R U . . .
C11 C 0.80605(13) 0.33219(11) 0.80233(11) 0.0114(2) Uani 1 1 d . . . . .
C12 C 0.77464(13) 0.29664(11) 0.89637(11) 0.0121(2) Uani 1 1 d . . . . .
C13 C 0.64039(13) 0.30450(11) 0.91085(11) 0.0124(2) Uani 1 1 d . . . . .
C14 C 0.53613(13) 0.34966(11) 0.82620(11) 0.0130(2) Uani 1 1 d . . . . .
H14 H 0.444513 0.355989 0.833342 0.016 Uiso 1 1 calc R U . . .
C15 C 0.95282(13) 0.32072(12) 0.78682(11) 0.0130(2) Uani 1 1 d . . . . .
C16 C 0.95812(14) 0.36796(14) 0.67902(12) 0.0195(3) Uani 1 1 d . . . . .
H16A H 0.889927 0.315813 0.603797 0.029 Uiso 1 1 calc R U . . .
H16B H 1.053908 0.364025 0.674165 0.029 Uiso 1 1 calc R U . . .
H16C H 0.933910 0.454281 0.690113 0.029 Uiso 1 1 calc R U . . .
C17 C 1.07072(13) 0.39994(13) 0.89934(12) 0.0173(3) Uani 1 1 d . . . . .
H17A H 1.162733 0.389325 0.887601 0.026 Uiso 1 1 calc R U . . .
H17C H 1.071787 0.373085 0.971217 0.026 Uiso 1 1 calc R U . . .
H17D H 1.052672 0.487824 0.910823 0.026 Uiso 1 1 calc R U . . .
C18 C 0.98614(15) 0.18423(13) 0.76284(14) 0.0213(3) Uani 1 1 d . . . . .
H18A H 0.909949 0.133902 0.692122 0.032 Uiso 1 1 calc R U . . .
H18B H 0.993551 0.153658 0.834091 0.032 Uiso 1 1 calc R U . . .
H18C H 1.076200 0.177981 0.746983 0.032 Uiso 1 1 calc R U . . .
C19 C 0.60814(13) 0.26554(12) 1.01469(11) 0.0148(2) Uani 1 1 d . . . . .
C20 C 0.69885(15) 0.34987(13) 1.13955(12) 0.0191(3) Uani 1 1 d . . . . .
H20A H 0.799701 0.344013 1.150169 0.029 Uiso 1 1 calc R U . . .
H20B H 0.677390 0.322856 1.203946 0.029 Uiso 1 1 calc R U . . .
H20C H 0.677072 0.436286 1.143832 0.029 Uiso 1 1 calc R U . . .
C21 C 0.63039(16) 0.12711(13) 1.00945(13) 0.0212(3) Uani 1 1 d . . . . .
H21A H 0.572889 0.075114 0.929333 0.032 Uiso 1 1 calc R U . . .
H21B H 0.601560 0.103678 1.072192 0.032 Uiso 1 1 calc R U . . .
H21C H 0.730824 0.114796 1.023502 0.032 Uiso 1 1 calc R U . . .
C22 C 0.45242(15) 0.27898(16) 1.00558(13) 0.0236(3) Uani 1 1 d . . . . .
H22A H 0.433335 0.366271 1.012263 0.035 Uiso 1 1 calc R U . . .
H22B H 0.434599 0.252018 1.071475 0.035 Uiso 1 1 calc R U . . .
H22C H 0.390063 0.227215 0.927202 0.035 Uiso 1 1 calc R U . . .
C23 C 0.31186(13) 0.35687(12) 0.57093(11) 0.0123(2) Uani 1 1 d . . . . .
C24 C 0.29539(13) 0.23063(12) 0.56586(12) 0.0151(2) Uani 1 1 d . . . . .
H24 H 0.372668 0.193381 0.610568 0.018 Uiso 1 1 calc R U . . .
C25 C 0.16777(14) 0.15831(12) 0.49648(12) 0.0162(2) Uani 1 1 d . . . . .
H25 H 0.157412 0.072675 0.494124 0.019 Uiso 1 1 calc R U . . .
C26 C 0.05640(13) 0.21342(12) 0.43107(11) 0.0145(2) Uani 1 1 d . . . . .
C27 C 0.06902(13) 0.33874(12) 0.43410(12) 0.0154(2) Uani 1 1 d . . . . .
H27 H -0.008505 0.375261 0.388778 0.019 Uiso 1 1 calc R U . . .
C28 C 0.19594(13) 0.40953(12) 0.50398(11) 0.0145(2) Uani 1 1 d . . . . .
H28 H 0.204923 0.495390 0.506780 0.017 Uiso 1 1 calc R U . . .
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
C12 O1 H1 109.6(18) . . ?
C1 N1 N2 119.24(11) . . ?
N1 N2 C2 119.47(11) . . ?
N1 N2 H1N 120.0(12) . . ?
C2 N2 H1N 118.8(12) . . ?
N1 C1 C23 115.62(11) . . ?
N1 C1 C9 124.29(11) . . ?
C23 C1 C9 120.08(10) . . ?
N2 C2 C3 121.34(11) . . ?
N2 C2 C7 118.60(11) . . ?
C3 C2 C7 120.06(11) . . ?
C4 C3 C2 120.04(12) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C5 C4 C3 120.70(12) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 118.85(12) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C7 C6 C5 121.99(12) . . ?
C7 C6 H6 119.0 . . ?
C5 C6 H6 119.0 . . ?
C6 C7 C2 118.37(12) . . ?
C6 C7 C8 120.51(12) . . ?
C2 C7 C8 121.12(12) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C14 C9 C10 118.85(11) . . ?
C14 C9 C1 120.54(11) . . ?
C10 C9 C1 120.61(11) . . ?
C9 C10 C11 122.17(11) . . ?
C9 C10 H10 118.9 . . ?
C11 C10 H10 118.9 . . ?
C10 C11 C12 116.77(11) . . ?
C10 C11 C15 120.89(11) . . ?
C12 C11 C15 122.32(11) . . ?
O1 C12 C11 115.63(11) . . ?
O1 C12 C13 121.21(11) . . ?
C11 C12 C13 123.16(11) . . ?
C14 C13 C12 116.77(11) . . ?
C14 C13 C19 120.81(11) . . ?
C12 C13 C19 122.42(11) . . ?
C9 C14 C13 122.27(11) . . ?
C9 C14 H14 118.9 . . ?
C13 C14 H14 118.9 . . ?
C16 C15 C18 107.38(11) . . ?
C16 C15 C17 106.30(10) . . ?
C18 C15 C17 109.75(11) . . ?
C16 C15 C11 111.25(10) . . ?
C18 C15 C11 110.64(10) . . ?
C17 C15 C11 111.35(10) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
C15 C17 H17D 109.5 . . ?
H17A C17 H17D 109.5 . . ?
H17C C17 H17D 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C22 C19 C20 106.27(11) . . ?
C22 C19 C13 111.30(10) . . ?
C20 C19 C13 110.94(10) . . ?
C22 C19 C21 105.89(11) . . ?
C20 C19 C21 110.62(11) . . ?
C13 C19 C21 111.59(11) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 C28 118.19(11) . . ?
C24 C23 C1 121.76(11) . . ?
C28 C23 C1 120.05(11) . . ?
C25 C24 C23 121.24(11) . . ?
C25 C24 H24 119.4 . . ?
C23 C24 H24 119.4 . . ?
C26 C25 C24 118.82(12) . . ?
C26 C25 H25 120.6 . . ?
C24 C25 H25 120.6 . . ?
C25 C26 C27 121.47(12) . . ?
C25 C26 Br1 119.72(10) . . ?
C27 C26 Br1 118.77(9) . . ?
C28 C27 C26 119.07(11) . . ?
C28 C27 H27 120.5 . . ?
C26 C27 H27 120.5 . . ?
C27 C28 C23 121.21(12) . . ?
C27 C28 H28 119.4 . . ?
C23 C28 H28 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 C26 1.8985(12) . ?
O1 C12 1.3727(15) . ?
O1 H1 0.71(2) . ?
N1 C1 1.2956(16) . ?
N1 N2 1.3538(15) . ?
N2 C2 1.3962(16) . ?
N2 H1N 0.860(19) . ?
C1 C23 1.4827(17) . ?
C1 C9 1.4923(16) . ?
C2 C3 1.3971(17) . ?
C2 C7 1.4064(17) . ?
C3 C4 1.3882(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.3907(19) . ?
C5 H5 0.9500 . ?
C6 C7 1.3901(19) . ?
C6 H6 0.9500 . ?
C7 C8 1.5058(18) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C14 1.3937(16) . ?
C9 C10 1.3952(17) . ?
C10 C11 1.3971(17) . ?
C10 H10 0.9500 . ?
C11 C12 1.4105(16) . ?
C11 C15 1.5424(16) . ?
C12 C13 1.4108(17) . ?
C13 C14 1.3955(17) . ?
C13 C19 1.5443(16) . ?
C14 H14 0.9500 . ?
C15 C16 1.5315(17) . ?
C15 C18 1.5350(18) . ?
C15 C17 1.5398(18) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17C 0.9800 . ?
C17 H17D 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C22 1.5374(18) . ?
C19 C20 1.5433(18) . ?
C19 C21 1.5464(19) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.3968(17) . ?
C23 C28 1.4041(17) . ?
C24 C25 1.3932(18) . ?
C24 H24 0.9500 . ?
C25 C26 1.3833(18) . ?
C25 H25 0.9500 . ?
C26 C27 1.3892(18) . ?
C27 C28 1.3820(18) . ?
C27 H27 0.9500 . ?
C28 H28 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
C1 N1 N2 C2 -170.54(11) . . . . ?
N2 N1 C1 C23 178.71(10) . . . . ?
N2 N1 C1 C9 -0.39(18) . . . . ?
N1 N2 C2 C3 -1.86(18) . . . . ?
N1 N2 C2 C7 178.42(11) . . . . ?
N2 C2 C3 C4 -178.72(12) . . . . ?
C7 C2 C3 C4 1.00(19) . . . . ?
C2 C3 C4 C5 -0.5(2) . . . . ?
C3 C4 C5 C6 -0.3(2) . . . . ?
C4 C5 C6 C7 0.7(2) . . . . ?
C5 C6 C7 C2 -0.19(19) . . . . ?
C5 C6 C7 C8 179.74(12) . . . . ?
N2 C2 C7 C6 179.08(12) . . . . ?
C3 C2 C7 C6 -0.64(18) . . . . ?
N2 C2 C7 C8 -0.85(18) . . . . ?
C3 C2 C7 C8 179.43(12) . . . . ?
N1 C1 C9 C14 120.47(14) . . . . ?
C23 C1 C9 C14 -58.59(16) . . . . ?
N1 C1 C9 C10 -59.01(17) . . . . ?
C23 C1 C9 C10 121.93(13) . . . . ?
C14 C9 C10 C11 0.05(19) . . . . ?
C1 C9 C10 C11 179.54(11) . . . . ?
C9 C10 C11 C12 0.05(18) . . . . ?
C9 C10 C11 C15 178.80(11) . . . . ?
C10 C11 C12 O1 179.83(11) . . . . ?
C15 C11 C12 O1 1.09(17) . . . . ?
C10 C11 C12 C13 -0.18(18) . . . . ?
C15 C11 C12 C13 -178.92(11) . . . . ?
O1 C12 C13 C14 -179.81(11) . . . . ?
C11 C12 C13 C14 0.20(18) . . . . ?
O1 C12 C13 C19 0.20(18) . . . . ?
C11 C12 C13 C19 -179.79(11) . . . . ?
C10 C9 C14 C13 -0.03(19) . . . . ?
C1 C9 C14 C13 -179.51(11) . . . . ?
C12 C13 C14 C9 -0.09(19) . . . . ?
C19 C13 C14 C9 179.90(11) . . . . ?
C10 C11 C15 C16 2.29(16) . . . . ?
C12 C11 C15 C16 -179.03(11) . . . . ?
C10 C11 C15 C18 -116.99(13) . . . . ?
C12 C11 C15 C18 61.70(15) . . . . ?
C10 C11 C15 C17 120.67(12) . . . . ?
C12 C11 C15 C17 -60.64(15) . . . . ?
C14 C13 C19 C22 2.24(17) . . . . ?
C12 C13 C19 C22 -177.77(12) . . . . ?
C14 C13 C19 C20 -115.86(13) . . . . ?
C12 C13 C19 C20 64.13(16) . . . . ?
C14 C13 C19 C21 120.30(13) . . . . ?
C12 C13 C19 C21 -59.71(16) . . . . ?
N1 C1 C23 C24 169.43(12) . . . . ?
C9 C1 C23 C24 -11.43(17) . . . . ?
N1 C1 C23 C28 -10.01(17) . . . . ?
C9 C1 C23 C28 169.13(11) . . . . ?
C28 C23 C24 C25 0.01(18) . . . . ?
C1 C23 C24 C25 -179.44(11) . . . . ?
C23 C24 C25 C26 0.48(19) . . . . ?
C24 C25 C26 C27 -0.55(19) . . . . ?
C24 C25 C26 Br1 -178.50(9) . . . . ?
C25 C26 C27 C28 0.11(19) . . . . ?
Br1 C26 C27 C28 178.08(9) . . . . ?
C26 C27 C28 C23 0.40(19) . . . . ?
C24 C23 C28 C27 -0.46(18) . . . . ?
C1 C23 C28 C27 179.00(11) . . . . ?
