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#$Date: 2024-07-05 02:35:40 +0300 (Fri, 05 Jul 2024) $
#$Revision: 292743 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/33/7063331.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_7063331
loop_
_publ_author_name
'Yang, Jing'
'Hu, Xing-Mei'
'Zhao, Ke-Hua'
'Huang, Kun'
'Yan, Sheng-Jiao'
_publ_section_title
;
 Cu(ii)-catalyzed annulation of α,β-unsaturated ketoxime acetates with
 3-formylchromones for the synthesis of functionalized 2,4-diarylpyridines
;
_journal_issue                   26
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              11682
_journal_page_last               11687
_journal_paper_doi               10.1039/D4NJ01648C
_journal_volume                  48
_journal_year                    2024
_chemical_formula_moiety         'C27 H22 Br N O2'
_chemical_formula_sum            'C27 H22 Br N O2'
_chemical_formula_weight         472.36
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-08-10
_audit_creation_method
;
FinalCif V88 by Daniel Kratzert, Freiburg 2022,
https://github.com/dkratzert/FinalCif
;
_audit_update_record
;
2023-06-28 deposited with the CCDC.	2024-06-06 downloaded from the CCDC.
;
_cell_angle_alpha                110.335(2)
_cell_angle_beta                 99.439(2)
_cell_angle_gamma                92.472(2)
_cell_formula_units_Z            2
_cell_length_a                   9.2238(5)
_cell_length_b                   10.8056(5)
_cell_length_c                   12.0232(7)
_cell_measurement_reflns_used    4700
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      27.96
_cell_measurement_theta_min      2.25
_cell_volume                     1101.93(10)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'Bruker APEX4'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_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  0.0604
_diffrn_reflns_av_unetI/netI     0.0597
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            19730
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.342
_diffrn_reflns_theta_min         2.022
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.889
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6562
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1614 before and 0.0510 after correction.
The Ratio of minimum to maximum transmission is 0.8800.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_description       block
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         5483
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0401
_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)+(0.0265P)²+0.4218P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0711
_refine_ls_wR_factor_ref         0.0818
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3750
_reflns_number_total             5483
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4nj01648c2.cif
_cod_data_source_block           1
_cod_database_code               7063331
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C9(H9), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19), C21(H21), C23(H23), C24(H24), C26(H26), C27(H27)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C3(H3A,H3B,H3C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_olex2_submission_special_instructions 'No special instructions were received'
_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   0.681
_shelx_estimated_absorpt_t_max   0.805
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
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 0.17468(3) -0.21869(2) -0.07784(3) 0.04609(10) Uani 1 1 d . . . . .
O1 O 0.64936(18) 1.06275(14) 0.35390(16) 0.0389(4) Uani 1 1 d . . . . .
H1 H 0.562699 1.024956 0.335452 0.058 Uiso 1 1 calc R U . . .
O2 O 0.44536(17) 0.86355(15) 0.27421(15) 0.0359(4) Uani 1 1 d . . . . .
N1 N 0.35236(19) 0.44916(17) 0.07518(16) 0.0274(4) Uani 1 1 d . . . . .
C1 C 1.1659(3) 0.6937(2) 0.3698(2) 0.0401(6) Uani 1 1 d . . . . .
H1A H 1.218122 0.783057 0.411758 0.060 Uiso 1 1 calc R U . . .
H1B H 1.237978 0.628894 0.352319 0.060 Uiso 1 1 calc R U . . .
H1C H 1.103656 0.673187 0.421147 0.060 Uiso 1 1 calc R U . . .
C2 C 1.0695(2) 0.6875(2) 0.2519(2) 0.0308(5) Uani 1 1 d . . . . .
H2 H 1.134232 0.716600 0.204611 0.037 Uiso 1 1 calc R U . . .
C3 C 1.0032(3) 0.5446(2) 0.1771(2) 0.0392(6) Uani 1 1 d . . . . .
H3A H 0.944599 0.511346 0.223892 0.059 Uiso 1 1 calc R U . . .
H3B H 1.083019 0.488634 0.157123 0.059 Uiso 1 1 calc R U . . .
H3C H 0.939619 0.542186 0.102491 0.059 Uiso 1 1 calc R U . . .
C4 C 0.9529(2) 0.7834(2) 0.27769(19) 0.0252(5) Uani 1 1 d . . . . .
C5 C 0.9958(3) 0.9212(2) 0.3272(2) 0.0317(5) Uani 1 1 d . . . . .
H5 H 1.097888 0.952197 0.344056 0.038 Uiso 1 1 calc R U . . .
C6 C 0.8952(3) 1.0122(2) 0.3521(2) 0.0329(5) Uani 1 1 d . . . . .
H6 H 0.928053 1.104439 0.384580 0.039 Uiso 1 1 calc R U . . .
C7 C 0.7457(3) 0.9700(2) 0.3298(2) 0.0289(5) Uani 1 1 d . . . . .
C8 C 0.6982(2) 0.83292(19) 0.28397(19) 0.0239(5) Uani 1 1 d . . . . .
C9 C 0.8048(2) 0.74295(19) 0.25742(18) 0.0238(5) Uani 1 1 d . . . . .
H9 H 0.772856 0.650531 0.224116 0.029 Uiso 1 1 calc R U . . .
C10 C 0.5425(2) 0.7864(2) 0.26494(19) 0.0262(5) Uani 1 1 d . . . . .
C11 C 0.4953(2) 0.6416(2) 0.23085(19) 0.0235(5) Uani 1 1 d . . . . .
C12 C 0.5404(2) 0.5668(2) 0.30280(19) 0.0233(4) Uani 1 1 d . . . . .
C13 C 0.6352(2) 0.6269(2) 0.42455(19) 0.0253(5) Uani 1 1 d . . . . .
C14 C 0.6096(2) 0.7492(2) 0.5051(2) 0.0289(5) Uani 1 1 d . . . . .
H14 H 0.528546 0.792747 0.482983 0.035 Uiso 1 1 calc R U . . .
C15 C 0.7011(3) 0.8072(2) 0.6167(2) 0.0338(5) Uani 1 1 d . . . . .
H15 H 0.684000 0.891094 0.670292 0.041 Uiso 1 1 calc R U . . .
C16 C 0.8174(3) 0.7438(2) 0.6506(2) 0.0362(6) Uani 1 1 d . . . . .
H16 H 0.879990 0.783858 0.727573 0.043 Uiso 1 1 calc R U . . .
C17 C 0.8431(3) 0.6216(2) 0.5723(2) 0.0380(6) Uani 1 1 d . . . . .
H17 H 0.923440 0.578110 0.595630 0.046 Uiso 1 1 calc R U . . .
C18 C 0.7518(3) 0.5630(2) 0.4601(2) 0.0323(5) Uani 1 1 d . . . . .
H18 H 0.768807 0.478621 0.407188 0.039 Uiso 1 1 calc R U . . .
C19 C 0.4891(2) 0.4326(2) 0.25605(19) 0.0253(5) Uani 1 1 d . . . . .
H19 H 0.516235 0.378475 0.302072 0.030 Uiso 1 1 calc R U . . .
C20 C 0.3987(2) 0.3767(2) 0.14303(19) 0.0246(5) Uani 1 1 d . . . . .
C21 C 0.4009(2) 0.5779(2) 0.12049(19) 0.0267(5) Uani 1 1 d . . . . .
H21 H 0.368372 0.630062 0.073809 0.032 Uiso 1 1 calc R U . . .
C22 C 0.3440(2) 0.2330(2) 0.09100(19) 0.0248(5) Uani 1 1 d . . . . .
C23 C 0.4229(3) 0.1405(2) 0.12472(19) 0.0287(5) Uani 1 1 d . . . . .
H23 H 0.512836 0.169667 0.182149 0.034 Uiso 1 1 calc R U . . .
C24 C 0.3719(3) 0.0064(2) 0.0755(2) 0.0320(5) Uani 1 1 d . . . . .
H24 H 0.426350 -0.056315 0.098582 0.038 Uiso 1 1 calc R U . . .
C25 C 0.2412(3) -0.0342(2) -0.0071(2) 0.0314(5) Uani 1 1 d . . . . .
C26 C 0.1594(3) 0.0550(2) -0.0418(2) 0.0328(5) Uani 1 1 d . . . . .
H26 H 0.068710 0.025282 -0.098226 0.039 Uiso 1 1 calc R U . . .
C27 C 0.2120(3) 0.1887(2) 0.0074(2) 0.0305(5) Uani 1 1 d . . . . .
H27 H 0.157201 0.250753 -0.016389 0.037 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'
Br Br -0.2901 2.4595 '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'
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
C7 O1 H1 109.5 . . ?
C21 N1 C20 116.75(19) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C1 C2 H2 107.8 . . ?
C1 C2 C3 110.3(2) . . ?
C3 C2 H2 107.8 . . ?
C4 C2 C1 110.16(18) . . ?
C4 C2 H2 107.8 . . ?
C4 C2 C3 112.89(18) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C5 C4 C2 119.81(19) . . ?
C9 C4 C2 123.25(18) . . ?
C9 C4 C5 116.9(2) . . ?
C4 C5 H5 118.9 . . ?
C6 C5 C4 122.2(2) . . ?
C6 C5 H5 118.9 . . ?
C5 C6 H6 119.9 . . ?
C5 C6 C7 120.22(19) . . ?
C7 C6 H6 119.9 . . ?
O1 C7 C6 118.55(19) . . ?
O1 C7 C8 122.0(2) . . ?
C6 C7 C8 119.5(2) . . ?
C7 C8 C10 120.41(19) . . ?
C9 C8 C7 118.43(19) . . ?
C9 C8 C10 121.16(18) . . ?
C4 C9 C8 122.66(18) . . ?
C4 C9 H9 118.7 . . ?
C8 C9 H9 118.7 . . ?
O2 C10 C8 121.80(19) . . ?
O2 C10 C11 118.18(19) . . ?
C8 C10 C11 120.01(18) . . ?
C12 C11 C10 124.38(19) . . ?
C21 C11 C10 117.40(19) . . ?
C21 C11 C12 118.21(19) . . ?
C11 C12 C13 122.37(18) . . ?
C19 C12 C11 116.91(19) . . ?
C19 C12 C13 120.70(19) . . ?
C14 C13 C12 120.5(2) . . ?
C18 C13 C12 120.56(19) . . ?
C18 C13 C14 118.9(2) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.4(2) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.3(2) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 120.0(2) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 C16 120.1(2) . . ?
C18 C17 H17 120.0 . . ?
C13 C18 H18 119.8 . . ?
C17 C18 C13 120.3(2) . . ?
C17 C18 H18 119.8 . . ?
C12 C19 H19 119.6 . . ?
C20 C19 C12 120.7(2) . . ?
C20 C19 H19 119.6 . . ?
N1 C20 C19 122.36(19) . . ?
N1 C20 C22 116.11(19) . . ?
C19 C20 C22 121.5(2) . . ?
N1 C21 C11 125.0(2) . . ?
N1 C21 H21 117.5 . . ?
C11 C21 H21 117.5 . . ?
C23 C22 C20 121.02(19) . . ?
C27 C22 C20 120.2(2) . . ?
C27 C22 C23 118.76(19) . . ?
C22 C23 H23 119.6 . . ?
C24 C23 C22 120.9(2) . . ?
C24 C23 H23 119.6 . . ?
C23 C24 H24 120.6 . . ?
C25 C24 C23 118.9(2) . . ?
C25 C24 H24 120.6 . . ?
C24 C25 Br1 118.76(17) . . ?
C24 C25 C26 121.8(2) . . ?
C26 C25 Br1 119.46(17) . . ?
C25 C26 H26 120.6 . . ?
C25 C26 C27 118.8(2) . . ?
C27 C26 H26 120.6 . . ?
C22 C27 H27 119.6 . . ?
C26 C27 C22 120.9(2) . . ?
C26 C27 H27 119.6 . . ?
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 C25 1.902(2) . ?
O1 H1 0.8400 . ?
O1 C7 1.356(3) . ?
O2 C10 1.242(3) . ?
N1 C20 1.349(3) . ?
N1 C21 1.331(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.523(3) . ?
C2 H2 1.0000 . ?
C2 C3 1.529(3) . ?
C2 C4 1.519(3) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.409(3) . ?
C4 C9 1.372(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.373(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.386(3) . ?
C7 C8 1.409(3) . ?
C8 C9 1.408(3) . ?
C8 C10 1.455(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.497(3) . ?
C11 C12 1.404(3) . ?
C11 C21 1.389(3) . ?
C12 C13 1.483(3) . ?
C12 C19 1.390(3) . ?
C13 C14 1.398(3) . ?
C13 C18 1.391(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.379(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.378(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.386(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.385(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C19 C20 1.386(3) . ?
C20 C22 1.486(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.393(3) . ?
C22 C27 1.391(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.388(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.375(3) . ?
C25 C26 1.383(3) . ?
C26 H26 0.9500 . ?
C26 C27 1.386(3) . ?
C27 H27 0.9500 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O2 0.84 1.85 2.592(2) 145.7 . yes
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
Br1 C25 C26 C27 -177.70(17) . . . . ?
O1 C7 C8 C9 177.8(2) . . . . ?
O1 C7 C8 C10 -2.2(3) . . . . ?
O2 C10 C11 C12 -119.8(2) . . . . ?
O2 C10 C11 C21 60.2(3) . . . . ?
N1 C20 C22 C23 154.9(2) . . . . ?
N1 C20 C22 C27 -25.3(3) . . . . ?
C1 C2 C4 C5 67.1(3) . . . . ?
C1 C2 C4 C9 -111.5(2) . . . . ?
C2 C4 C5 C6 179.9(2) . . . . ?
C2 C4 C9 C8 178.7(2) . . . . ?
C3 C2 C4 C5 -169.2(2) . . . . ?
C3 C2 C4 C9 12.2(3) . . . . ?
C4 C5 C6 C7 0.7(4) . . . . ?
C5 C4 C9 C8 0.0(3) . . . . ?
C5 C6 C7 O1 -179.1(2) . . . . ?
C5 C6 C7 C8 1.4(3) . . . . ?
C6 C7 C8 C9 -2.6(3) . . . . ?
C6 C7 C8 C10 177.3(2) . . . . ?
C7 C8 C9 C4 2.0(3) . . . . ?
C7 C8 C10 O2 8.7(3) . . . . ?
C7 C8 C10 C11 -172.5(2) . . . . ?
C8 C10 C11 C12 61.4(3) . . . . ?
C8 C10 C11 C21 -118.6(2) . . . . ?
C9 C4 C5 C6 -1.4(3) . . . . ?
C9 C8 C10 O2 -171.3(2) . . . . ?
C9 C8 C10 C11 7.5(3) . . . . ?
C10 C8 C9 C4 -178.0(2) . . . . ?
C10 C11 C12 C13 3.1(3) . . . . ?
C10 C11 C12 C19 -178.42(19) . . . . ?
C10 C11 C21 N1 177.8(2) . . . . ?
C11 C12 C13 C14 42.5(3) . . . . ?
C11 C12 C13 C18 -137.0(2) . . . . ?
C11 C12 C19 C20 0.5(3) . . . . ?
C12 C11 C21 N1 -2.1(3) . . . . ?
C12 C13 C14 C15 -177.67(19) . . . . ?
C12 C13 C18 C17 177.8(2) . . . . ?
C12 C19 C20 N1 -2.2(3) . . . . ?
C12 C19 C20 C22 179.36(19) . . . . ?
C13 C12 C19 C20 179.05(19) . . . . ?
C13 C14 C15 C16 -1.1(3) . . . . ?
C14 C13 C18 C17 -1.8(3) . . . . ?
C14 C15 C16 C17 0.3(3) . . . . ?
C15 C16 C17 C18 -0.2(4) . . . . ?
C16 C17 C18 C13 0.9(4) . . . . ?
C18 C13 C14 C15 1.9(3) . . . . ?
C19 C12 C13 C14 -136.0(2) . . . . ?
C19 C12 C13 C18 44.5(3) . . . . ?
C19 C20 C22 C23 -26.7(3) . . . . ?
C19 C20 C22 C27 153.2(2) . . . . ?
C20 N1 C21 C11 0.5(3) . . . . ?
C20 C22 C23 C24 -179.7(2) . . . . ?
C20 C22 C27 C26 -179.8(2) . . . . ?
C21 N1 C20 C19 1.7(3) . . . . ?
C21 N1 C20 C22 -179.79(18) . . . . ?
C21 C11 C12 C13 -177.00(19) . . . . ?
C21 C11 C12 C19 1.5(3) . . . . ?
C22 C23 C24 C25 -0.3(3) . . . . ?
C23 C22 C27 C26 0.0(3) . . . . ?
C23 C24 C25 Br1 178.16(17) . . . . ?
C23 C24 C25 C26 -0.3(3) . . . . ?
C24 C25 C26 C27 0.8(4) . . . . ?
C25 C26 C27 C22 -0.6(3) . . . . ?
C27 C22 C23 C24 0.4(3) . . . . ?
