#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:35:45 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178433 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/54/4025449.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_4025449
loop_
_publ_author_name
'Lei Zhang'
'Deju Ye'
'Yu Zhou'
'Guannan Liu'
'Enguang Feng'
'Hualiang Jiang'
'Hong Liu'
_publ_section_title
;
 Regioselective Synthesis of 3-Benzazepinones and Unexpected
 5-Bromo-3-benzazepinones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3671
_journal_page_last               3677
_journal_paper_doi               10.1021/jo100378u
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C18 H16 Br N O'
_chemical_formula_weight         342.23
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 105.566(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.7440(12)
_cell_length_b                   14.3064(14)
_cell_length_c                   17.7456(17)
_cell_measurement_reflns_used    3238
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      49.015
_cell_measurement_theta_min      4.372
_cell_volume                     3116.7(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0438
_diffrn_reflns_av_sigmaI/netI    0.0681
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16260
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.86
_exptl_absorpt_coefficient_mu    2.636
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59607
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.302
_exptl_crystal_size_min          0.211
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.619
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.869
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         5785
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.869
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0402
_refine_ls_shift/su_max          0.038
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0430P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0885
_refine_ls_wR_factor_ref         0.0945
_reflns_number_gt                3259
_reflns_number_total             5785
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo100378u_si_002.cif
_cod_data_source_block           cd29285
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4025449
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.65431(3) 0.25140(3) 0.10316(2) 0.06035(15) Uani 1 1 d . . .
Br2 Br 1.19139(3) 0.97758(3) 0.13883(3) 0.07274(17) Uani 1 1 d . . .
N1 N 0.3467(2) 0.2924(2) 0.14048(17) 0.0480(7) Uani 1 1 d . . .
N2 N 0.8718(2) 0.9105(2) 0.13823(17) 0.0528(8) Uani 1 1 d . . .
O1 O 0.2053(2) 0.39119(19) 0.11477(16) 0.0741(8) Uani 1 1 d . . .
O2 O 0.7498(2) 0.7938(2) 0.10124(16) 0.0758(9) Uani 1 1 d . . .
C1 C 0.2883(3) 0.3645(3) 0.1004(2) 0.0515(10) Uani 1 1 d . . .
C2 C 0.3337(3) 0.4099(3) 0.0399(2) 0.0566(10) Uani 1 1 d . . .
H2A H 0.3496 0.3624 0.0054 0.068 Uiso 1 1 calc R . .
H2B H 0.2802 0.4524 0.0085 0.068 Uiso 1 1 calc R . .
C3 C 0.4358(3) 0.4627(3) 0.0780(2) 0.0509(10) Uani 1 1 d . . .
C4 C 0.5295(3) 0.4136(3) 0.1162(2) 0.0477(9) Uani 1 1 d . . .
C5 C 0.5259(3) 0.3120(3) 0.11916(19) 0.0446(9) Uani 1 1 d . . .
C6 C 0.4464(3) 0.2568(3) 0.12890(19) 0.0453(9) Uani 1 1 d . . .
C7 C 0.4382(4) 0.5590(3) 0.0753(2) 0.0719(12) Uani 1 1 d . . .
H7 H 0.3754 0.5922 0.0512 0.086 Uiso 1 1 calc R . .
C8 C 0.5345(5) 0.6062(3) 0.1088(3) 0.0833(16) Uani 1 1 d . . .
H8 H 0.5362 0.6711 0.1061 0.100 Uiso 1 1 calc R . .
C9 C 0.6272(4) 0.5585(4) 0.1457(3) 0.0764(13) Uani 1 1 d . . .
H9 H 0.6915 0.5906 0.1680 0.092 Uiso 1 1 calc R . .
C10 C 0.6244(3) 0.4637(3) 0.1493(2) 0.0599(11) Uani 1 1 d . . .
H10 H 0.6873 0.4314 0.1746 0.072 Uiso 1 1 calc R . .
C11 C 0.2990(3) 0.2431(3) 0.1964(2) 0.0661(12) Uani 1 1 d . . .
H11A H 0.2943 0.2851 0.2376 0.099 Uiso 1 1 calc R . .
H11B H 0.3442 0.1908 0.2183 0.099 Uiso 1 1 calc R . .
H11C H 0.2274 0.2213 0.1698 0.099 Uiso 1 1 calc R . .
C12 C 0.4535(3) 0.1528(2) 0.1292(2) 0.0430(9) Uani 1 1 d . . .
C13 C 0.5099(3) 0.1038(3) 0.1946(2) 0.0560(10) Uani 1 1 d . . .
H13 H 0.5451 0.1359 0.2399 0.067 Uiso 1 1 calc R . .
C14 C 0.5143(3) 0.0079(3) 0.1930(3) 0.0658(12) Uani 1 1 d . . .
H14 H 0.5517 -0.0237 0.2380 0.079 Uiso 1 1 calc R . .
C15 C 0.4663(3) -0.0420(3) 0.1285(3) 0.0637(12) Uani 1 1 d . . .
C16 C 0.4125(3) 0.0071(3) 0.0623(3) 0.0649(12) Uani 1 1 d . . .
H16 H 0.3807 -0.0254 0.0165 0.078 Uiso 1 1 calc R . .
C17 C 0.4049(3) 0.1031(3) 0.0630(2) 0.0534(10) Uani 1 1 d . . .
H17 H 0.3664 0.1345 0.0182 0.064 Uiso 1 1 calc R . .
C18 C 0.4703(4) -0.1468(3) 0.1269(3) 0.1052(18) Uani 1 1 d . . .
H18A H 0.4088 -0.1699 0.0874 0.158 Uiso 1 1 calc R . .
H18B H 0.4683 -0.1709 0.1770 0.158 Uiso 1 1 calc R . .
H18C H 0.5363 -0.1665 0.1154 0.158 Uiso 1 1 calc R . .
C19 C 0.8312(3) 0.8336(3) 0.0941(2) 0.0560(10) Uani 1 1 d . . .
C20 C 0.8933(3) 0.8021(3) 0.0383(2) 0.0586(11) Uani 1 1 d . . .
H20A H 0.8492 0.7595 0.0001 0.070 Uiso 1 1 calc R . .
H20B H 0.9117 0.8555 0.0106 0.070 Uiso 1 1 calc R . .
C21 C 0.9949(3) 0.7540(3) 0.0834(2) 0.0528(10) Uani 1 1 d . . .
C22 C 1.0764(3) 0.8066(3) 0.1332(2) 0.0513(10) Uani 1 1 d . . .
C23 C 1.0617(3) 0.9075(3) 0.13894(19) 0.0492(10) Uani 1 1 d . . .
C24 C 0.9721(3) 0.9556(3) 0.13896(19) 0.0508(10) Uani 1 1 d . . .
C25 C 1.0092(4) 0.6588(3) 0.0773(2) 0.0681(12) Uani 1 1 d . . .
H25 H 0.9542 0.6233 0.0448 0.082 Uiso 1 1 calc R . .
C26 C 1.1030(4) 0.6163(3) 0.1182(3) 0.0817(14) Uani 1 1 d . . .
H26 H 1.1121 0.5524 0.1128 0.098 Uiso 1 1 calc R . .
C27 C 1.1832(4) 0.6672(4) 0.1668(3) 0.0853(15) Uani 1 1 d . . .
H27 H 1.2466 0.6377 0.1950 0.102 Uiso 1 1 calc R . .
C28 C 1.1716(3) 0.7612(3) 0.1745(2) 0.0709(12) Uani 1 1 d . . .
H28 H 1.2274 0.7954 0.2075 0.085 Uiso 1 1 calc R . .
C29 C 0.8097(3) 0.9479(3) 0.1897(2) 0.0760(13) Uani 1 1 d . . .
H29A H 0.7337 0.9492 0.1623 0.114 Uiso 1 1 calc R . .
H29B H 0.8341 1.0102 0.2054 0.114 Uiso 1 1 calc R . .
H29C H 0.8204 0.9089 0.2351 0.114 Uiso 1 1 calc R . .
C30 C 0.9656(3) 1.0592(3) 0.1386(2) 0.0497(10) Uani 1 1 d . . .
C31 C 1.0184(3) 1.1132(3) 0.2019(2) 0.0652(11) Uani 1 1 d . . .
H31 H 1.0603 1.0847 0.2471 0.078 Uiso 1 1 calc R . .
C32 C 1.0094(3) 1.2093(4) 0.1984(3) 0.0722(13) Uani 1 1 d . . .
H32 H 1.0460 1.2443 0.2416 0.087 Uiso 1 1 calc R . .
C33 C 0.9486(3) 1.2547(3) 0.1338(3) 0.0598(11) Uani 1 1 d . . .
C34 C 0.8947(3) 1.2005(3) 0.0714(2) 0.0643(11) Uani 1 1 d . . .
H34 H 0.8524 1.2294 0.0265 0.077 Uiso 1 1 calc R . .
C35 C 0.9020(3) 1.1043(3) 0.0739(2) 0.0551(10) Uani 1 1 d . . .
H35 H 0.8634 1.0694 0.0313 0.066 Uiso 1 1 calc R . .
C36 C 0.9394(4) 1.3595(3) 0.1319(3) 0.0933(16) Uani 1 1 d . . .
H36A H 0.9309 1.3815 0.1810 0.140 Uiso 1 1 calc R . .
H36B H 0.8773 1.3779 0.0906 0.140 Uiso 1 1 calc R . .
H36C H 1.0042 1.3861 0.1229 0.140 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
C1 N1 C6 125.3(3) . . ?
C1 N1 C11 116.6(3) . . ?
C6 N1 C11 117.9(3) . . ?
C19 N2 C24 124.7(3) . . ?
C19 N2 C29 117.8(3) . . ?
C24 N2 C29 117.5(3) . . ?
O1 C1 N1 121.1(4) . . ?
O1 C1 C2 122.7(3) . . ?
N1 C1 C2 116.2(3) . . ?
C3 C2 C1 110.5(3) . . ?
C3 C2 H2A 109.5 . . ?
C1 C2 H2A 109.6 . . ?
C3 C2 H2B 109.6 . . ?
C1 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
C7 C3 C4 119.7(4) . . ?
C7 C3 C2 120.8(4) . . ?
C4 C3 C2 119.5(3) . . ?
C10 C4 C3 118.7(4) . . ?
C10 C4 C5 122.0(4) . . ?
C3 C4 C5 119.3(3) . . ?
C6 C5 C4 129.0(3) . . ?
C6 C5 Br1 117.1(3) . . ?
C4 C5 Br1 113.9(2) . . ?
C5 C6 N1 122.8(3) . . ?
C5 C6 C12 123.0(3) . . ?
N1 C6 C12 114.2(3) . . ?
C3 C7 C8 119.8(4) . . ?
C3 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C9 C8 C7 120.8(4) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C10 C9 C8 119.3(4) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C9 C10 C4 121.6(4) . . ?
C9 C10 H10 119.2 . . ?
C4 C10 H10 119.2 . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C17 C12 C13 118.1(4) . . ?
C17 C12 C6 120.1(3) . . ?
C13 C12 C6 121.8(3) . . ?
C14 C13 C12 120.3(4) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C15 C14 C13 122.3(4) . . ?
C15 C14 H14 118.8 . . ?
C13 C14 H14 118.8 . . ?
C14 C15 C16 117.5(4) . . ?
C14 C15 C18 122.3(4) . . ?
C16 C15 C18 120.2(5) . . ?
C17 C16 C15 121.3(4) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C12 C17 C16 120.5(4) . . ?
C12 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
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 . . ?
O2 C19 N2 121.2(4) . . ?
O2 C19 C20 123.0(4) . . ?
N2 C19 C20 115.8(3) . . ?
C21 C20 C19 108.7(3) . . ?
C21 C20 H20A 110.0 . . ?
C19 C20 H20A 110.0 . . ?
C21 C20 H20B 109.9 . . ?
C19 C20 H20B 110.0 . . ?
H20A C20 H20B 108.3 . . ?
C25 C21 C22 119.5(4) . . ?
C25 C21 C20 121.7(4) . . ?
C22 C21 C20 118.9(4) . . ?
C21 C22 C28 118.4(4) . . ?
C21 C22 C23 119.4(3) . . ?
C28 C22 C23 122.1(4) . . ?
C24 C23 C22 129.4(3) . . ?
C24 C23 Br2 117.7(3) . . ?
C22 C23 Br2 112.7(3) . . ?
C23 C24 N2 122.1(4) . . ?
C23 C24 C30 124.2(3) . . ?
N2 C24 C30 113.7(3) . . ?
C26 C25 C21 120.9(4) . . ?
C26 C25 H25 119.6 . . ?
C21 C25 H25 119.6 . . ?
C27 C26 C25 120.1(5) . . ?
C27 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
C26 C27 C28 120.6(4) . . ?
C26 C27 H27 119.7 . . ?
C28 C27 H27 119.7 . . ?
C27 C28 C22 120.6(4) . . ?
C27 C28 H28 119.7 . . ?
C22 C28 H28 119.7 . . ?
N2 C29 H29A 109.5 . . ?
N2 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
N2 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C35 C30 C31 117.8(4) . . ?
C35 C30 C24 119.4(3) . . ?
C31 C30 C24 122.8(4) . . ?
C32 C31 C30 120.3(4) . . ?
C32 C31 H31 119.8 . . ?
C30 C31 H31 119.8 . . ?
C33 C32 C31 122.3(4) . . ?
C33 C32 H32 118.9 . . ?
C31 C32 H32 118.9 . . ?
C32 C33 C34 117.2(4) . . ?
C32 C33 C36 121.1(4) . . ?
C34 C33 C36 121.6(4) . . ?
C33 C34 C35 121.4(4) . . ?
C33 C34 H34 119.3 . . ?
C35 C34 H34 119.3 . . ?
C30 C35 C34 121.0(4) . . ?
C30 C35 H35 119.5 . . ?
C34 C35 H35 119.5 . . ?
C33 C36 H36A 109.5 . . ?
C33 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C33 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 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 C5 1.939(3) . ?
Br2 C23 1.934(3) . ?
N1 C1 1.356(4) . ?
N1 C6 1.433(4) . ?
N1 C11 1.476(4) . ?
N2 C19 1.369(5) . ?
N2 C24 1.429(4) . ?
N2 C29 1.461(4) . ?
O1 C1 1.213(4) . ?
O2 C19 1.219(4) . ?
C1 C2 1.499(5) . ?
C2 C3 1.499(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C7 1.380(5) . ?
C3 C4 1.394(5) . ?
C4 C10 1.392(5) . ?
C4 C5 1.456(5) . ?
C5 C6 1.333(4) . ?
C6 C12 1.491(4) . ?
C7 C8 1.387(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.369(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.359(5) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C17 1.370(5) . ?
C12 C13 1.381(5) . ?
C13 C14 1.373(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.348(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.382(5) . ?
C15 C18 1.501(5) . ?
C16 C17 1.378(5) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.495(5) . ?
C20 C21 1.495(5) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C25 1.381(5) . ?
C21 C22 1.391(5) . ?
C22 C28 1.398(5) . ?
C22 C23 1.463(5) . ?
C23 C24 1.332(5) . ?
C24 C30 1.485(5) . ?
C25 C26 1.363(6) . ?
C25 H25 0.9300 . ?
C26 C27 1.359(6) . ?
C26 H26 0.9300 . ?
C27 C28 1.363(6) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 C35 1.375(5) . ?
C30 C31 1.380(5) . ?
C31 C32 1.379(5) . ?
C31 H31 0.9300 . ?
C32 C33 1.363(6) . ?
C32 H32 0.9300 . ?
C33 C34 1.375(5) . ?
C33 C36 1.504(5) . ?
C34 C35 1.380(5) . ?
C34 H34 0.9300 . ?
C35 H35 0.9300 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 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
C35 H35 Br2 0.93 2.99 3.825(4) 150.8 3_775
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 N1 C1 O1 -178.9(3) . . . . ?
C11 N1 C1 O1 5.6(5) . . . . ?
C6 N1 C1 C2 -0.5(5) . . . . ?
C11 N1 C1 C2 -176.0(3) . . . . ?
O1 C1 C2 C3 109.0(4) . . . . ?
N1 C1 C2 C3 -69.4(4) . . . . ?
C1 C2 C3 C7 -111.4(4) . . . . ?
C1 C2 C3 C4 68.9(4) . . . . ?
C7 C3 C4 C10 -1.5(5) . . . . ?
C2 C3 C4 C10 178.2(3) . . . . ?
C7 C3 C4 C5 179.5(3) . . . . ?
C2 C3 C4 C5 -0.8(5) . . . . ?
C10 C4 C5 C6 142.3(4) . . . . ?
C3 C4 C5 C6 -38.8(5) . . . . ?
C10 C4 C5 Br1 -39.9(4) . . . . ?
C3 C4 C5 Br1 139.0(3) . . . . ?
C4 C5 C6 N1 -1.6(6) . . . . ?
Br1 C5 C6 N1 -179.4(2) . . . . ?
C4 C5 C6 C12 178.8(3) . . . . ?
Br1 C5 C6 C12 1.0(5) . . . . ?
C1 N1 C6 C5 42.9(5) . . . . ?
C11 N1 C6 C5 -141.6(4) . . . . ?
C1 N1 C6 C12 -137.5(4) . . . . ?
C11 N1 C6 C12 38.0(4) . . . . ?
C4 C3 C7 C8 1.8(6) . . . . ?
C2 C3 C7 C8 -177.9(4) . . . . ?
C3 C7 C8 C9 -1.1(6) . . . . ?
C7 C8 C9 C10 0.1(7) . . . . ?
C8 C9 C10 C4 0.2(6) . . . . ?
C3 C4 C10 C9 0.5(5) . . . . ?
C5 C4 C10 C9 179.4(3) . . . . ?
C5 C6 C12 C17 -98.6(4) . . . . ?
N1 C6 C12 C17 81.8(4) . . . . ?
C5 C6 C12 C13 80.3(5) . . . . ?
N1 C6 C12 C13 -99.3(4) . . . . ?
C17 C12 C13 C14 -1.5(5) . . . . ?
C6 C12 C13 C14 179.6(3) . . . . ?
C12 C13 C14 C15 1.1(6) . . . . ?
C13 C14 C15 C16 0.7(6) . . . . ?
C13 C14 C15 C18 -179.5(4) . . . . ?
C14 C15 C16 C17 -2.2(6) . . . . ?
C18 C15 C16 C17 178.0(4) . . . . ?
C13 C12 C17 C16 0.1(5) . . . . ?
C6 C12 C17 C16 179.0(3) . . . . ?
C15 C16 C17 C12 1.8(6) . . . . ?
C24 N2 C19 O2 173.7(3) . . . . ?
C29 N2 C19 O2 -4.8(5) . . . . ?
C24 N2 C19 C20 -5.8(5) . . . . ?
C29 N2 C19 C20 175.7(3) . . . . ?
O2 C19 C20 C21 -104.1(4) . . . . ?
N2 C19 C20 C21 75.3(4) . . . . ?
C19 C20 C21 C25 110.7(4) . . . . ?
C19 C20 C21 C22 -68.6(4) . . . . ?
C25 C21 C22 C28 1.3(6) . . . . ?
C20 C21 C22 C28 -179.3(3) . . . . ?
C25 C21 C22 C23 179.3(3) . . . . ?
C20 C21 C22 C23 -1.3(5) . . . . ?
C21 C22 C23 C24 38.8(6) . . . . ?
C28 C22 C23 C24 -143.4(4) . . . . ?
C21 C22 C23 Br2 -136.5(3) . . . . ?
C28 C22 C23 Br2 41.4(4) . . . . ?
C22 C23 C24 N2 4.3(6) . . . . ?
Br2 C23 C24 N2 179.4(2) . . . . ?
C22 C23 C24 C30 -174.8(3) . . . . ?
Br2 C23 C24 C30 0.2(5) . . . . ?
C19 N2 C24 C23 -41.2(5) . . . . ?
C29 N2 C24 C23 137.2(4) . . . . ?
C19 N2 C24 C30 138.0(3) . . . . ?
C29 N2 C24 C30 -43.6(4) . . . . ?
C22 C21 C25 C26 -1.4(6) . . . . ?
C20 C21 C25 C26 179.2(4) . . . . ?
C21 C25 C26 C27 1.1(7) . . . . ?
C25 C26 C27 C28 -0.8(7) . . . . ?
C26 C27 C28 C22 0.8(7) . . . . ?
C21 C22 C28 C27 -1.0(6) . . . . ?
C23 C22 C28 C27 -178.9(4) . . . . ?
C23 C24 C30 C35 112.7(4) . . . . ?
N2 C24 C30 C35 -66.5(4) . . . . ?
C23 C24 C30 C31 -69.3(5) . . . . ?
N2 C24 C30 C31 111.6(4) . . . . ?
C35 C30 C31 C32 -1.8(6) . . . . ?
C24 C30 C31 C32 -179.9(3) . . . . ?
C30 C31 C32 C33 0.4(6) . . . . ?
C31 C32 C33 C34 0.7(6) . . . . ?
C31 C32 C33 C36 179.4(4) . . . . ?
C32 C33 C34 C35 -0.2(6) . . . . ?
C36 C33 C34 C35 -178.9(4) . . . . ?
C31 C30 C35 C34 2.3(5) . . . . ?
C24 C30 C35 C34 -179.5(3) . . . . ?
C33 C34 C35 C30 -1.4(6) . . . . ?
