#------------------------------------------------------------------------------
#$Date: 2020-10-06 13:18:22 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257790 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/96/7059691.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_7059691
loop_
_publ_author_name
'Wu, Hai-tao'
'Wang, Lan-zhi'
_publ_section_title
;
 Expedient green-chemistry approaches for a one-pot synthesis of two
 series of novel 1,5-benzodiazepines via domino reactions
;
_journal_issue                   25
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              10428
_journal_page_last               10440
_journal_paper_doi               10.1039/C9NJ06332C
_journal_volume                  44
_journal_year                    2020
_chemical_formula_sum            'C22 H22 Br Cl N2 O4'
_chemical_formula_weight         493.77
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/1
_audit_update_record
;
2018-12-24 deposited with the CCDC.	2020-06-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.169(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.3147(12)
_cell_length_b                   13.7035(11)
_cell_length_c                   12.3387(11)
_cell_measurement_reflns_used    2194
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      20.557
_cell_measurement_theta_min      2.303
_cell_volume                     2272.0(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_unetI/netI     0.0813
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11171
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.019
_diffrn_reflns_theta_max         25.019
_diffrn_reflns_theta_min         2.302
_exptl_absorpt_coefficient_mu    1.957
_exptl_absorpt_correction_T_max  0.9564
_exptl_absorpt_correction_T_min  0.5914
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.023
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4005
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.1016
_refine_ls_R_factor_gt           0.0465
_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)+(0.0005P)²+1.2720P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0995
_refine_ls_wR_factor_ref         0.1187
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2329
_reflns_number_total             4005
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9nj06332c2.cif
_cod_data_source_block           181221c
_cod_depositor_comments
;Adding full bibliography for 7059691.cif.

 Adding full bibliography for 7059691.cif.
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7059691
_shelx_shelxl_version_number     2018/1
_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   0.591
_shelx_estimated_absorpt_t_max   0.956
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
Br1 Br 0.24270(8) 0.6764(2) 0.5804(3) 0.0987(7) Uani 0.801(8) 1 d . U P A 1
Cl1 Cl 1.0596(3) 0.5654(4) 0.6498(4) 0.1124(14) Uani 0.677(7) 1 d . U P B 1
Br1' Br 0.2468(4) 0.6478(6) 0.5424(8) 0.0987(7) Uani 0.199(8) 1 d . . P A 2
Cl1' Cl 1.0882(6) 0.6082(7) 0.7011(8) 0.1124(14) Uani 0.323(7) 1 d . . P B 2
N1 N 0.62859(19) 0.70658(19) 0.6952(2) 0.0470(7) Uani 1 1 d . . . . .
H1 H 0.631465 0.643936 0.699098 0.056 Uiso 1 1 calc R U . . .
N2 N 0.6082(2) 0.86438(18) 0.5290(2) 0.0456(7) Uani 1 1 d . . . . .
H2 H 0.601727 0.873053 0.457731 0.055 Uiso 1 1 calc R U . . .
O1 O 0.62383(19) 0.87931(17) 0.86387(19) 0.0621(7) Uani 1 1 d . . . . .
O2 O 0.5927(2) 0.99504(18) 0.7294(2) 0.0728(8) Uani 1 1 d . . . . .
O3 O 0.83321(17) 1.02121(18) 0.4572(2) 0.0610(7) Uani 1 1 d . . . . .
O4 O 0.68517(18) 0.94679(16) 0.37677(19) 0.0518(6) Uani 1 1 d . . . . .
C1 C 0.6348(3) 0.9218(3) 0.7720(3) 0.0527(10) Uani 1 1 d . . . . .
C2 C 0.7104(3) 0.8694(2) 0.7319(3) 0.0481(9) Uani 1 1 d . . . . .
H2A H 0.775088 0.897343 0.777222 0.058 Uiso 1 1 calc R U . . .
C3 C 0.6954(3) 0.8935(2) 0.6079(3) 0.0449(8) Uani 1 1 d . . . . .
C4 C 0.7663(2) 0.9417(2) 0.5790(3) 0.0496(9) Uani 1 1 d . . . . .
H4 H 0.824839 0.958570 0.638001 0.060 Uiso 1 1 calc R U . . .
C5 C 0.7564(3) 0.9681(2) 0.4635(3) 0.0455(8) Uani 1 1 d . . . . .
C6 C 0.7199(2) 0.7589(2) 0.7570(3) 0.0449(8) Uani 1 1 d . . . . .
H6 H 0.732277 0.750533 0.839631 0.054 Uiso 1 1 calc R U . . .
C7 C 0.8076(2) 0.7152(2) 0.7327(3) 0.0498(9) Uani 1 1 d . . . . .
C8 C 0.9008(3) 0.7104(3) 0.8172(4) 0.0844(14) Uani 1 1 d . . . . .
H8 H 0.909651 0.735318 0.890231 0.101 Uiso 1 1 calc R U . . .
C9 C 0.9811(3) 0.6693(4) 0.7960(6) 0.1094(19) Uani 1 1 d . . . . .
H9 H 1.043475 0.667613 0.853557 0.131 Uiso 1 1 calc R U . . .
C10 C 0.9677(4) 0.6314(4) 0.6893(6) 0.0923(16) Uani 1 1 d . . . . .
C11 C 0.8779(3) 0.6357(4) 0.6045(4) 0.0877(14) Uani 1 1 d . . . . .
H11 H 0.869492 0.610646 0.531668 0.105 Uiso 1 1 calc R U . . .
C12 C 0.7987(3) 0.6778(3) 0.6268(4) 0.0700(11) Uani 1 1 d . . . . .
H12 H 0.737235 0.680703 0.567819 0.084 Uiso 1 1 calc R U . . .
C13 C 0.5369(2) 0.7470(2) 0.6303(3) 0.0399(8) Uani 1 1 d . . . . .
C14 C 0.5269(2) 0.8216(2) 0.5499(3) 0.0410(8) Uani 1 1 d . . . . .
C15 C 0.4320(3) 0.8521(2) 0.4817(3) 0.0531(9) Uani 1 1 d . . . . .
H15 H 0.425547 0.903733 0.430639 0.064 Uiso 1 1 calc R U . . .
C16 C 0.3484(3) 0.8083(3) 0.4877(3) 0.0670(11) Uani 1 1 d . . . . .
H16 H 0.285627 0.828315 0.439988 0.080 Uiso 1 1 calc R U . . .
C17 C 0.3590(3) 0.7339(3) 0.5659(3) 0.0604(10) Uani 1 1 d . . . . .
C18 C 0.4509(3) 0.7050(2) 0.6376(3) 0.0491(9) Uani 1 1 d . . . . .
H18 H 0.455911 0.656594 0.692131 0.059 Uiso 1 1 calc R U . . .
C19 C 0.5544(3) 0.9257(3) 0.9107(3) 0.0694(12) Uani 1 1 d . . . . .
H19A H 0.561311 0.995997 0.908379 0.083 Uiso 1 1 calc R U . . .
H19B H 0.570517 0.906540 0.990792 0.083 Uiso 1 1 calc R U . . .
C20 C 0.4491(4) 0.8980(3) 0.8444(4) 0.0870(14) Uani 1 1 d . . . . .
H20A H 0.432012 0.919459 0.765897 0.130 Uiso 1 1 calc R U . . .
H20B H 0.405640 0.928384 0.878716 0.130 Uiso 1 1 calc R U . . .
H20C H 0.442160 0.828407 0.846079 0.130 Uiso 1 1 calc R U . . .
C21 C 0.8281(3) 1.0537(3) 0.3440(3) 0.0686(11) Uani 1 1 d . . . . .
H21A H 0.772366 1.097840 0.312161 0.082 Uiso 1 1 calc R U . . .
H21B H 0.818967 0.998284 0.292412 0.082 Uiso 1 1 calc R U . . .
C22 C 0.9236(3) 1.1047(4) 0.3564(4) 0.0964(15) Uani 1 1 d . . . . .
H22A H 0.932111 1.158986 0.408115 0.145 Uiso 1 1 calc R U . . .
H22B H 0.921775 1.127751 0.282274 0.145 Uiso 1 1 calc R U . . .
H22C H 0.978069 1.060078 0.386862 0.145 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'
Cl Cl 0.1484 0.1585 '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
C13 N1 C6 127.1(3) . . ?
C13 N1 H1 116.5 . . ?
C6 N1 H1 116.5 . . ?
C3 N2 C14 127.5(3) . . ?
C3 N2 H2 116.2 . . ?
C14 N2 H2 116.2 . . ?
C1 O1 C19 116.4(3) . . ?
C5 O3 C21 117.0(3) . . ?
O2 C1 O1 123.5(4) . . ?
O2 C1 C2 124.2(3) . . ?
O1 C1 C2 112.2(3) . . ?
C3 C2 C1 111.1(3) . . ?
C3 C2 C6 113.0(3) . . ?
C1 C2 C6 115.0(3) . . ?
C3 C2 H2A 105.6 . . ?
C1 C2 H2A 105.6 . . ?
C6 C2 H2A 105.6 . . ?
N2 C3 C4 122.9(3) . . ?
N2 C3 C2 116.1(3) . . ?
C4 C3 C2 121.0(3) . . ?
C3 C4 C5 124.0(3) . . ?
C3 C4 H4 118.0 . . ?
C5 C4 H4 118.0 . . ?
O4 C5 O3 121.8(3) . . ?
O4 C5 C4 125.0(3) . . ?
O3 C5 C4 113.2(3) . . ?
N1 C6 C7 111.0(3) . . ?
N1 C6 C2 112.2(3) . . ?
C7 C6 C2 111.8(3) . . ?
N1 C6 H6 107.2 . . ?
C7 C6 H6 107.2 . . ?
C2 C6 H6 107.2 . . ?
C12 C7 C8 116.8(4) . . ?
C12 C7 C6 121.8(3) . . ?
C8 C7 C6 121.4(4) . . ?
C7 C8 C9 121.6(5) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 H8 119.2 . . ?
C10 C9 C8 119.2(4) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C11 C10 C9 120.7(5) . . ?
C11 C10 Cl1' 137.5(6) . . ?
C9 C10 Cl1' 100.7(6) . . ?
C11 C10 Cl1 113.7(5) . . ?
C9 C10 Cl1 125.4(5) . . ?
C10 C11 C12 119.4(5) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C7 C12 C11 122.3(4) . . ?
C7 C12 H12 118.8 . . ?
C11 C12 H12 118.8 . . ?
C18 C13 N1 118.6(3) . . ?
C18 C13 C14 118.2(3) . . ?
N1 C13 C14 123.0(3) . . ?
C15 C14 C13 119.3(3) . . ?
C15 C14 N2 117.4(3) . . ?
C13 C14 N2 123.2(3) . . ?
C16 C15 C14 121.7(3) . . ?
C16 C15 H15 119.1 . . ?
C14 C15 H15 119.1 . . ?
C15 C16 C17 118.6(3) . . ?
C15 C16 H16 120.7 . . ?
C17 C16 H16 120.7 . . ?
C18 C17 C16 121.1(3) . . ?
C18 C17 Br1 119.8(3) . . ?
C16 C17 Br1 119.0(3) . . ?
C18 C17 Br1' 119.0(3) . . ?
C16 C17 Br1' 117.6(3) . . ?
C17 C18 C13 121.0(3) . . ?
C17 C18 H18 119.5 . . ?
C13 C18 H18 119.5 . . ?
O1 C19 C20 111.7(3) . . ?
O1 C19 H19A 109.3 . . ?
C20 C19 H19A 109.3 . . ?
O1 C19 H19B 109.3 . . ?
C20 C19 H19B 109.3 . . ?
H19A C19 H19B 107.9 . . ?
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 . . ?
O3 C21 C22 107.8(3) . . ?
O3 C21 H21A 110.2 . . ?
C22 C21 H21A 110.2 . . ?
O3 C21 H21B 110.2 . . ?
C22 C21 H21B 110.2 . . ?
H21A C21 H21B 108.5 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
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 C17 1.905(4) . ?
Cl1 C10 1.797(6) . ?
Br1' C17 1.932(7) . ?
Cl1' C10 1.711(8) . ?
N1 C13 1.395(4) . ?
N1 C6 1.455(4) . ?
N1 H1 0.8600 . ?
N2 C3 1.352(4) . ?
N2 C14 1.404(4) . ?
N2 H2 0.8600 . ?
O1 C1 1.331(4) . ?
O1 C19 1.457(4) . ?
O2 C1 1.196(4) . ?
O3 C5 1.343(4) . ?
O3 C21 1.444(4) . ?
O4 C5 1.232(4) . ?
C1 C2 1.516(5) . ?
C2 C3 1.507(4) . ?
C2 C6 1.542(4) . ?
C2 H2A 0.9800 . ?
C3 C4 1.357(4) . ?
C4 C5 1.429(4) . ?
C4 H4 0.9300 . ?
C6 C7 1.512(5) . ?
C6 H6 0.9800 . ?
C7 C12 1.368(5) . ?
C7 C8 1.382(5) . ?
C8 C9 1.385(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.366(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.349(6) . ?
C11 C12 1.381(5) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C18 1.390(4) . ?
C13 C14 1.397(4) . ?
C14 C15 1.392(4) . ?
C15 C16 1.364(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.376(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.366(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.494(5) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.495(5) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
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
N1 H1 O4 0.86 2.40 2.974(3) 124.2 4_576 yes
N2 H2 O4 0.86 2.07 2.729(3) 133.3 . yes
C4 H4 Cl1^a 0.93 2.96 3.812(5) 153.3 2_756 yes
C15 H15 O2 0.93 2.35 3.265(4) 166.6 3_676 yes
C18 H18 O2 0.93 2.61 3.474(4) 155.7 2_646 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
C19 O1 C1 O2 1.5(5) . . . . ?
C19 O1 C1 C2 178.6(3) . . . . ?
O2 C1 C2 C3 -23.7(5) . . . . ?
O1 C1 C2 C3 159.2(3) . . . . ?
O2 C1 C2 C6 -153.6(3) . . . . ?
O1 C1 C2 C6 29.3(4) . . . . ?
C14 N2 C3 C4 -174.3(3) . . . . ?
C14 N2 C3 C2 5.7(5) . . . . ?
C1 C2 C3 N2 -63.9(4) . . . . ?
C6 C2 C3 N2 67.1(4) . . . . ?
C1 C2 C3 C4 116.1(4) . . . . ?
C6 C2 C3 C4 -112.9(4) . . . . ?
N2 C3 C4 C5 0.9(5) . . . . ?
C2 C3 C4 C5 -179.1(3) . . . . ?
C21 O3 C5 O4 0.9(5) . . . . ?
C21 O3 C5 C4 -178.2(3) . . . . ?
C3 C4 C5 O4 -3.4(5) . . . . ?
C3 C4 C5 O3 175.7(3) . . . . ?
C13 N1 C6 C7 -133.1(3) . . . . ?
C13 N1 C6 C2 -7.2(4) . . . . ?
C3 C2 C6 N1 -65.1(4) . . . . ?
C1 C2 C6 N1 63.9(4) . . . . ?
C3 C2 C6 C7 60.4(4) . . . . ?
C1 C2 C6 C7 -170.6(3) . . . . ?
N1 C6 C7 C12 35.5(4) . . . . ?
C2 C6 C7 C12 -90.6(4) . . . . ?
N1 C6 C7 C8 -143.8(3) . . . . ?
C2 C6 C7 C8 90.0(4) . . . . ?
C12 C7 C8 C9 -0.2(6) . . . . ?
C6 C7 C8 C9 179.2(4) . . . . ?
C7 C8 C9 C10 -1.0(8) . . . . ?
C8 C9 C10 C11 1.6(8) . . . . ?
C8 C9 C10 Cl1' 171.4(5) . . . . ?
C8 C9 C10 Cl1 -173.8(4) . . . . ?
C9 C10 C11 C12 -1.0(8) . . . . ?
Cl1' C10 C11 C12 -166.1(7) . . . . ?
Cl1 C10 C11 C12 175.0(4) . . . . ?
C8 C7 C12 C11 0.8(6) . . . . ?
C6 C7 C12 C11 -178.5(4) . . . . ?
C10 C11 C12 C7 -0.3(7) . . . . ?
C6 N1 C13 C18 -140.1(3) . . . . ?
C6 N1 C13 C14 46.3(4) . . . . ?
C18 C13 C14 C15 0.9(4) . . . . ?
N1 C13 C14 C15 174.6(3) . . . . ?
C18 C13 C14 N2 -175.2(3) . . . . ?
N1 C13 C14 N2 -1.6(5) . . . . ?
C3 N2 C14 C15 139.1(3) . . . . ?
C3 N2 C14 C13 -44.7(5) . . . . ?
C13 C14 C15 C16 -2.8(5) . . . . ?
N2 C14 C15 C16 173.5(3) . . . . ?
C14 C15 C16 C17 1.8(6) . . . . ?
C15 C16 C17 C18 1.0(6) . . . . ?
C15 C16 C17 Br1 177.0(3) . . . . ?
C15 C16 C17 Br1' -161.6(5) . . . . ?
C16 C17 C18 C13 -2.9(6) . . . . ?
Br1 C17 C18 C13 -178.9(3) . . . . ?
Br1' C17 C18 C13 159.5(5) . . . . ?
N1 C13 C18 C17 -172.0(3) . . . . ?
C14 C13 C18 C17 1.9(5) . . . . ?
C1 O1 C19 C20 81.3(4) . . . . ?
C5 O3 C21 C22 -176.1(3) . . . . ?
