#------------------------------------------------------------------------------
#$Date: 2023-03-04 20:28:16 +0200 (Sat, 04 Mar 2023) $
#$Revision: 281492 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/21/7062126.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_7062126
loop_
_publ_author_name
'Mast, Nicolas'
'Erb, William'
'Nauton, Lionel'
'Moreau, Pascale'
'Mongin, Olivier'
'Roisnel, Thierry'
'Macaigne, Margaux'
'Robert, Thomas'
'Bach, Stéphane'
'Picot, Laurent'
'Thiéry, Valérie'
'Hurvois, Jean-Pierre'
'Mongin, Florence'
_publ_section_title
;
 From benzofuro-, benzothieno- and 10-methylindolo-[2,3-b]-fused
 benzothiopyrano[4,3,2-de]quinolines to the corresponding
 benzothiopyrano[4,3,2-de]1,8-naphthyridines: synthesis and properties of
 these hexacyclic heteroaromatic compounds
;
_journal_issue                   1
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              258
_journal_page_last               283
_journal_paper_doi               10.1039/D2NJ04567B
_journal_volume                  47
_journal_year                    2023
_chemical_absolute_configuration rm/ad/rmad/syn/unk/.
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C12 H7 Br Cl N O'
_chemical_formula_sum            'C12 H7 Br Cl N O'
_chemical_formula_weight         296.55
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2022-09-01 deposited with the CCDC.	2022-11-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.664(2)
_cell_length_b                   8.7402(15)
_cell_length_c                   18.815(4)
_cell_measurement_reflns_used    4999
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.5483
_cell_measurement_theta_min      2.5695
_cell_measurement_wavelength     0.710730
_cell_volume                     2247.0(7)
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2021)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018_2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 CMOS-PHOTON70
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_orient_matrix_UB_11      -0.0268156
_diffrn_orient_matrix_UB_12      0.0227229
_diffrn_orient_matrix_UB_13      0.0489623
_diffrn_orient_matrix_UB_21      -0.1033338
_diffrn_orient_matrix_UB_22      0.0205708
_diffrn_orient_matrix_UB_23      -0.0172472
_diffrn_orient_matrix_UB_31      -0.0411543
_diffrn_orient_matrix_UB_32      -0.0664569
_diffrn_orient_matrix_UB_33      0.0114025
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0684
_diffrn_reflns_av_unetI/netI     0.0730
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16394
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         2.165
_diffrn_source_current           1.00
_diffrn_source_power             50.0
_diffrn_source_voltage           50.00
_exptl_absorpt_coefficient_mu    3.871
_exptl_absorpt_correction_T_max  0.793
_exptl_absorpt_correction_T_min  0.525
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.753
_exptl_crystal_description       prism
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.810
_refine_diff_density_min         -0.489
_refine_diff_density_rms         0.159
_refine_ls_abs_structure_details
;
Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.03(4)
_refine_ls_extinction_coef       0.0116(18)
_refine_ls_extinction_method     'SHELXL-2018_3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         4810
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0893
_refine_ls_R_factor_gt           0.0564
_refine_ls_shift/su_max          0.031
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1105P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1482
_refine_ls_wR_factor_ref         0.1784
_reflns_Friedel_coverage         0.808
_reflns_Friedel_fraction_full    0.878
_reflns_Friedel_fraction_max     0.858
_reflns_number_gt                3506
_reflns_number_total             4810
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2nj04567b2.cif
_cod_data_source_block           NM215F2_2
_cod_depositor_comments
'Adding full bibliography for 7062120--7062126.cif.'
_cod_database_code               7062126
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, 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_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 0.62087(10) 0.59510(15) 0.25131(7) 0.0570(5) Uani 0.714(5) 1 d . . P A .
Cl1 Cl 0.62087(10) 0.59510(15) 0.25131(7) 0.0570(5) Uani 0.286(5) 1 d . . P A .
Cl11 Cl 0.34894(11) 0.62220(19) 0.35232(16) 0.0535(7) Uani 0.714(5) 1 d . . P A
.
Br11 Br 0.34894(11) 0.62220(19) 0.35232(16) 0.0535(7) Uani 0.286(5) 1 d . . P A
.
C1 C 0.6871(6) 0.4649(11) 0.3133(5) 0.039(2) Uani 1 1 d . . . . .
C2 C 0.7740(7) 0.4049(11) 0.2887(6) 0.048(2) Uani 0.714(5) 1 d . . P A 1
H2 H 0.799638 0.432135 0.243477 0.058 Uiso 0.714(5) 1 calc R U P A 1
N2 N 0.7740(7) 0.4049(11) 0.2887(6) 0.048(2) Uani 0.286(5) 1 d . . P A 2
C3 C 0.8230(6) 0.3015(12) 0.3335(6) 0.046(3) Uani 1 1 d . . . . .
H3 H 0.884907 0.262699 0.319305 0.055 Uiso 1 1 calc R U . A 1
C4 C 0.7843(8) 0.2551(12) 0.3967(9) 0.049(3) Uani 1 1 d . . . . .
H4 H 0.817202 0.181391 0.425153 0.059 Uiso 1 1 calc R U . . .
C5 C 0.6963(6) 0.3173(10) 0.4187(6) 0.039(2) Uani 1 1 d . . . . .
H5 H 0.668651 0.285855 0.462695 0.047 Uiso 1 1 calc R U . . .
C6 C 0.6478(6) 0.4255(9) 0.3775(5) 0.0335(19) Uani 1 1 d . . . . .
C7 C 0.5525(5) 0.4865(10) 0.4068(5) 0.0329(19) Uani 1 1 d . . . . .
O8 O 0.4938(4) 0.3982(7) 0.4333(4) 0.0449(17) Uani 1 1 d . . . . .
C9 C 0.5380(6) 0.6558(10) 0.4070(5) 0.0339(19) Uani 1 1 d . . . . .
C10 C 0.4491(7) 0.7265(11) 0.3908(8) 0.040(2) Uani 1 1 d . . . . .
N11 N 0.4346(7) 0.8783(9) 0.3969(6) 0.045(2) Uani 0.714(5) 1 d . . P A 1
C11 C 0.4346(7) 0.8783(9) 0.3969(6) 0.045(2) Uani 0.286(5) 1 d . . P A 2
H11 H 0.373337 0.922815 0.385007 0.054 Uiso 0.286(5) 1 calc R U P A 2
C12 C 0.5102(9) 0.9662(12) 0.4205(6) 0.051(3) Uani 1 1 d . . . . .
H12 H 0.500557 1.073228 0.425954 0.062 Uiso 1 1 calc R U . A 1
C13 C 0.6002(9) 0.9044(12) 0.4367(7) 0.050(3) Uani 1 1 d . . . . .
H13 H 0.652278 0.968463 0.451881 0.060 Uiso 1 1 calc R U . . .
C14 C 0.6139(7) 0.7486(11) 0.4306(9) 0.044(3) Uani 1 1 d . . . . .
H14 H 0.675331 0.704762 0.442566 0.053 Uiso 1 1 calc R U . . .
Br2 Br 0.88255(9) 0.59907(14) 0.75011(7) 0.0533(5) Uani 0.681(6) 1 d . . P B .
Cl2 Cl 0.88255(9) 0.59907(14) 0.75011(7) 0.0533(5) Uani 0.319(6) 1 d . . P B .
Cl12 Cl 0.60512(11) 0.6359(2) 0.64901(15) 0.0543(7) Uani 0.681(6) 1 d . . P B .
Br12 Br 0.60512(11) 0.6359(2) 0.64901(15) 0.0543(7) Uani 0.319(6) 1 d . . P B .
C21 C 0.9458(7) 0.4655(10) 0.6872(5) 0.041(2) Uani 1 1 d . . . . .
C22 C 1.0304(7) 0.4015(11) 0.7116(6) 0.047(2) Uani 0.681(6) 1 d . . P B 1
H22 H 1.056453 0.426860 0.756906 0.056 Uiso 0.681(6) 1 calc R U P B 1
N22 N 1.0304(7) 0.4015(11) 0.7116(6) 0.047(2) Uani 0.319(6) 1 d . . P B 2
C23 C 1.0769(7) 0.2966(12) 0.6666(7) 0.048(3) Uani 1 1 d . . . . .
H23 H 1.138487 0.255103 0.679823 0.057 Uiso 1 1 calc R U . B 1
C24 C 1.0349(8) 0.2534(10) 0.6042(8) 0.043(3) Uani 1 1 d . . . . .
H24 H 1.065822 0.178612 0.575198 0.052 Uiso 1 1 calc R U . . .
C25 C 0.9487(6) 0.3173(10) 0.5832(6) 0.036(2) Uani 1 1 d . . . . .
H25 H 0.919434 0.285155 0.539857 0.044 Uiso 1 1 calc R U . . .
C26 C 0.9033(6) 0.4275(9) 0.6236(5) 0.0325(18) Uani 1 1 d . . . . .
C27 C 0.8082(6) 0.4933(11) 0.5978(5) 0.036(2) Uani 1 1 d . . . . .
O28 O 0.7451(4) 0.4073(7) 0.5758(5) 0.0465(18) Uani 1 1 d . . . . .
C29 C 0.7966(5) 0.6620(10) 0.5943(5) 0.0336(19) Uani 1 1 d . . . . .
C30 C 0.7098(7) 0.7401(11) 0.6112(7) 0.036(2) Uani 1 1 d . . . . .
N31 N 0.6971(6) 0.8909(10) 0.6047(6) 0.049(2) Uani 0.681(6) 1 d . . P B 1
C31 C 0.6971(6) 0.8909(10) 0.6047(6) 0.049(2) Uani 0.319(6) 1 d . . P B 2
H31 H 0.637171 0.938836 0.617170 0.058 Uiso 0.319(6) 1 calc R U P B 2
C32 C 0.7719(8) 0.9699(12) 0.5800(6) 0.047(2) Uani 1 1 d . . . . .
H32 H 0.763769 1.077192 0.574332 0.056 Uiso 1 1 calc R U . B 1
C33 C 0.8601(8) 0.9085(11) 0.5621(7) 0.045(2) Uani 1 1 d . . . . .
H33 H 0.911799 0.970640 0.544524 0.054 Uiso 1 1 calc R U . . .
C34 C 0.8718(6) 0.7499(10) 0.5705(8) 0.038(3) Uani 1 1 d . . . . .
H34 H 0.932793 0.703567 0.559374 0.046 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'
Cl Cl 0.1484 0.1585 '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
C6 C1 N2 122.7(9) . . ?
C6 C1 C2 122.7(9) . . ?
C6 C1 Br1 121.1(6) . . ?
N2 C1 Br1 116.1(8) . . ?
C2 C1 Br1 116.1(8) . . ?
C1 C2 C3 116.9(10) . . ?
C1 C2 H2 121.5 . . ?
C3 C2 H2 121.5 . . ?
C1 N2 C3 116.9(10) . . ?
C4 C3 C2 122.0(9) . . ?
C4 C3 N2 122.0(9) . . ?
C4 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
C3 C4 C5 118.7(11) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C4 C5 C6 121.0(11) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 118.5(8) . . ?
C1 C6 C7 124.9(8) . . ?
C5 C6 C7 116.5(9) . . ?
O8 C7 C9 122.6(8) . . ?
O8 C7 C6 119.5(8) . . ?
C9 C7 C6 117.8(7) . . ?
C14 C9 C10 117.4(9) . . ?
C14 C9 C7 118.7(8) . . ?
C10 C9 C7 123.6(8) . . ?
C11 C10 C9 123.1(10) . . ?
N11 C10 C9 123.1(10) . . ?
C11 C10 Br11 114.9(8) . . ?
N11 C10 Br11 114.9(8) . . ?
C9 C10 Br11 121.7(8) . . ?
C10 N11 C12 118.2(9) . . ?
C10 C11 C12 118.2(9) . . ?
C10 C11 H11 120.9 . . ?
C12 C11 H11 120.9 . . ?
C11 C12 C13 121.8(9) . . ?
N11 C12 C13 121.8(9) . . ?
N11 C12 H12 119.1 . . ?
C13 C12 H12 119.1 . . ?
C12 C13 C14 119.4(10) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C13 C14 C9 120.1(10) . . ?
C13 C14 H14 119.9 . . ?
C9 C14 H14 119.9 . . ?
N22 C21 C26 123.7(9) . . ?
C22 C21 C26 123.7(9) . . ?
N22 C21 Br2 115.7(8) . . ?
C22 C21 Br2 115.7(8) . . ?
C26 C21 Br2 120.5(7) . . ?
C21 C22 C23 116.7(10) . . ?
C21 C22 H22 121.7 . . ?
C23 C22 H22 121.7 . . ?
C21 N22 C23 116.7(10) . . ?
C24 C23 C22 120.9(9) . . ?
C24 C23 N22 120.9(9) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C25 C24 C23 120.1(11) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C25 C26 121.1(10) . . ?
C24 C25 H25 119.5 . . ?
C26 C25 H25 119.4 . . ?
C21 C26 C25 117.5(8) . . ?
C21 C26 C27 123.8(8) . . ?
C25 C26 C27 118.7(9) . . ?
O28 C27 C29 121.5(8) . . ?
O28 C27 C26 119.1(8) . . ?
C29 C27 C26 119.2(7) . . ?
C34 C29 C30 116.0(9) . . ?
C34 C29 C27 119.7(7) . . ?
C30 C29 C27 124.3(8) . . ?
C31 C30 C29 124.7(10) . . ?
N31 C30 C29 124.7(10) . . ?
C31 C30 Br12 115.1(8) . . ?
N31 C30 Br12 115.1(8) . . ?
C29 C30 Br12 120.2(7) . . ?
C32 N31 C30 116.7(9) . . ?
C32 C31 C30 116.7(9) . . ?
C32 C31 H31 121.7 . . ?
C30 C31 H31 121.7 . . ?
C31 C32 C33 124.5(9) . . ?
N31 C32 C33 124.5(9) . . ?
N31 C32 H32 117.7 . . ?
C33 C32 H32 117.7 . . ?
C32 C33 C34 117.5(9) . . ?
C32 C33 H33 121.2 . . ?
C34 C33 H33 121.3 . . ?
C29 C34 C33 120.6(9) . . ?
C29 C34 H34 119.7 . . ?
C33 C34 H34 119.7 . . ?
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 C1 1.864(10) . ?
Br11 C10 1.797(11) . ?
C1 C6 1.365(14) . ?
C1 N2 1.379(12) . ?
C1 C2 1.379(12) . ?
C2 C3 1.406(16) . ?
C2 H2 0.9500 . ?
N2 C3 1.406(16) . ?
C3 C4 1.363(19) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(14) . ?
C4 H4 0.9500 . ?
C5 C6 1.392(13) . ?
C5 H5 0.9500 . ?
C6 C7 1.511(11) . ?
C7 O8 1.220(11) . ?
C7 C9 1.492(12) . ?
C9 C14 1.390(13) . ?
C9 C10 1.397(13) . ?
C10 C11 1.346(13) . ?
C10 N11 1.346(13) . ?
N11 C12 1.362(15) . ?
C11 C12 1.362(15) . ?
C11 H11 0.9500 . ?
C12 C13 1.377(16) . ?
C12 H12 0.9500 . ?
C13 C14 1.379(14) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
Br2 C21 1.874(10) . ?
Br12 C30 1.839(11) . ?
C21 N22 1.364(13) . ?
C21 C22 1.364(13) . ?
C21 C26 1.370(14) . ?
C22 C23 1.401(15) . ?
C22 H22 0.9500 . ?
N22 C23 1.401(15) . ?
C23 C24 1.360(19) . ?
C23 H23 0.9500 . ?
C24 C25 1.363(14) . ?
C24 H24 0.9500 . ?
C25 C26 1.375(12) . ?
C25 H25 0.9500 . ?
C26 C27 1.502(12) . ?
C27 O28 1.217(10) . ?
C27 C29 1.485(13) . ?
C29 C34 1.359(12) . ?
C29 C30 1.404(13) . ?
C30 C31 1.334(13) . ?
C30 N31 1.334(13) . ?
N31 C32 1.318(14) . ?
C31 C32 1.318(14) . ?
C31 H31 0.9500 . ?
C32 C33 1.361(14) . ?
C32 H32 0.9500 . ?
C33 C34 1.405(13) . ?
C33 H33 0.9500 . ?
C34 H34 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
C6 C1 C2 C3 -1.3(14) . . . . ?
Br1 C1 C2 C3 -177.4(7) . . . . ?
C6 C1 N2 C3 -1.3(14) . . . . ?
Br1 C1 N2 C3 -177.4(7) . . . . ?
C1 C2 C3 C4 3.7(16) . . . . ?
C1 N2 C3 C4 3.7(16) . . . . ?
C2 C3 C4 C5 -3.0(17) . . . . ?
N2 C3 C4 C5 -3.0(17) . . . . ?
C3 C4 C5 C6 -0.1(16) . . . . ?
N2 C1 C6 C5 -1.6(14) . . . . ?
C2 C1 C6 C5 -1.6(14) . . . . ?
Br1 C1 C6 C5 174.4(7) . . . . ?
N2 C1 C6 C7 -179.5(9) . . . . ?
C2 C1 C6 C7 -179.5(9) . . . . ?
Br1 C1 C6 C7 -3.5(13) . . . . ?
C4 C5 C6 C1 2.3(14) . . . . ?
C4 C5 C6 C7 -179.7(9) . . . . ?
C1 C6 C7 O8 134.3(10) . . . . ?
C5 C6 C7 O8 -43.6(12) . . . . ?
C1 C6 C7 C9 -50.4(13) . . . . ?
C5 C6 C7 C9 131.7(9) . . . . ?
O8 C7 C9 C14 129.6(12) . . . . ?
C6 C7 C9 C14 -45.5(14) . . . . ?
O8 C7 C9 C10 -44.4(16) . . . . ?
C6 C7 C9 C10 140.4(10) . . . . ?
C14 C9 C10 C11 0.2(18) . . . . ?
C7 C9 C10 C11 174.3(11) . . . . ?
C14 C9 C10 N11 0.2(18) . . . . ?
C7 C9 C10 N11 174.3(11) . . . . ?
C14 C9 C10 Br11 174.3(10) . . . . ?
C7 C9 C10 Br11 -11.6(16) . . . . ?
C9 C10 N11 C12 -0.6(18) . . . . ?
Br11 C10 N11 C12 -175.0(8) . . . . ?
C9 C10 C11 C12 -0.6(18) . . . . ?
Br11 C10 C11 C12 -175.0(8) . . . . ?
C10 C11 C12 C13 1.3(17) . . . . ?
C10 N11 C12 C13 1.3(17) . . . . ?
C11 C12 C13 C14 -1.6(19) . . . . ?
N11 C12 C13 C14 -1.6(19) . . . . ?
C12 C13 C14 C9 1(2) . . . . ?
C10 C9 C14 C13 -0.6(19) . . . . ?
C7 C9 C14 C13 -175.0(12) . . . . ?
C26 C21 C22 C23 3.0(15) . . . . ?
Br2 C21 C22 C23 177.5(7) . . . . ?
C26 C21 N22 C23 3.0(15) . . . . ?
Br2 C21 N22 C23 177.5(7) . . . . ?
C21 C22 C23 C24 -4.8(15) . . . . ?
C21 N22 C23 C24 -4.8(15) . . . . ?
C22 C23 C24 C25 2.9(16) . . . . ?
N22 C23 C24 C25 2.9(16) . . . . ?
C23 C24 C25 C26 1.0(14) . . . . ?
N22 C21 C26 C25 0.7(14) . . . . ?
C22 C21 C26 C25 0.7(14) . . . . ?
Br2 C21 C26 C25 -173.6(7) . . . . ?
N22 C21 C26 C27 177.6(9) . . . . ?
C22 C21 C26 C27 177.6(9) . . . . ?
Br2 C21 C26 C27 3.2(12) . . . . ?
C24 C25 C26 C21 -2.8(13) . . . . ?
C24 C25 C26 C27 -179.8(8) . . . . ?
C21 C26 C27 O28 -131.1(10) . . . . ?
C25 C26 C27 O28 45.7(12) . . . . ?
C21 C26 C27 C29 53.9(12) . . . . ?
C25 C26 C27 C29 -129.3(9) . . . . ?
O28 C27 C29 C34 -133.8(11) . . . . ?
C26 C27 C29 C34 41.0(14) . . . . ?
O28 C27 C29 C30 43.0(15) . . . . ?
C26 C27 C29 C30 -142.1(10) . . . . ?
C34 C29 C30 C31 0.6(18) . . . . ?
C27 C29 C30 C31 -176.3(11) . . . . ?
C34 C29 C30 N31 0.6(18) . . . . ?
C27 C29 C30 N31 -176.3(11) . . . . ?
C34 C29 C30 Br12 -176.4(10) . . . . ?
C27 C29 C30 Br12 6.7(15) . . . . ?
C29 C30 N31 C32 0.6(19) . . . . ?
Br12 C30 N31 C32 177.7(8) . . . . ?
C29 C30 C31 C32 0.6(19) . . . . ?
Br12 C30 C31 C32 177.7(8) . . . . ?
C30 C31 C32 C33 -1.0(18) . . . . ?
C30 N31 C32 C33 -1.0(18) . . . . ?
C31 C32 C33 C34 0.1(19) . . . . ?
N31 C32 C33 C34 0.1(19) . . . . ?
C30 C29 C34 C33 -1.5(18) . . . . ?
C27 C29 C34 C33 175.6(11) . . . . ?
C32 C33 C34 C29 1(2) . . . . ?
