#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/72/2017228.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2017228
loop_
_publ_author_name
'Stibrany, Robert T.'
'Potenza, Joseph A.'
_publ_section_title
;
 Structures of 1-hydrophenanthroimidazoles: building blocks in the
 synthesis of expanded-ring bis(imidazoles)
;
_journal_coeditor_code           FG3095
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o406
_journal_page_last               o409
_journal_paper_doi               10.1107/S0108270109025165
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C15 H8 Br2 N2 , 0.5H2 O'
_chemical_formula_moiety         'C15 H8 Br2 N2 , 0.5H2 O'
_chemical_formula_sum            'C15 H9 Br2 N2 O0.5'
_chemical_formula_weight         385.04
_chemical_melting_point          583
_chemical_name_systematic
;
3,6-dibromo-1-H-phenanthro[9,10-d]imidazole hemihydrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                101.683(4)
_cell_angle_beta                 101.398(5)
_cell_angle_gamma                104.109(5)
_cell_formula_units_Z            4
_cell_length_a                   8.415(2)
_cell_length_b                   10.139(2)
_cell_length_c                   17.227(4)
_cell_measurement_reflns_used    824
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.909
_cell_measurement_theta_min      2.182
_cell_volume                     1347.9(5)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics
;
ORTEPIII (Burnett & Johnson, 1996) and ORTEP32 (Farrugia, 1997)
;
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_sigmaI/netI    0.0539
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12857
_diffrn_reflns_theta_full        26.10
_diffrn_reflns_theta_max         26.10
_diffrn_reflns_theta_min         2.15
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.004
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.359
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Blessing, 1995)'
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_diffrn    1.898
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             748
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.19
_refine_diff_density_max         1.294
_refine_diff_density_min         -0.770
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     360
_refine_ls_number_reflns         5330
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0472
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0728P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1183
_refine_ls_wR_factor_ref         0.1278
_reflns_number_gt                3658
_reflns_number_total             5330
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fg3095.cif
_cod_data_source_block           II
_cod_database_code               2017228
_cod_database_fobs_code          2017228
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 1.1756(6) 0.6635(7) 0.2421(4) 0.1129(19) Uani d D 1 . .
H H1O 1.112(11) 0.724(9) 0.244(7) 0.18(5) Uiso d D 1 . .
H H2O 1.201(13) 0.718(10) 0.208(5) 0.20(5) Uiso d D 1 . .
Br Br53 0.43103(6) 0.24240(6) 0.61777(3) 0.06234(18) Uani d . 1 . .
Br Br63 1.04163(10) 0.97232(6) 0.67120(4) 0.0945(3) Uani d . 1 . .
N N41 0.9268(4) 0.5002(4) 0.2891(2) 0.0479(9) Uani d . 1 . .
H H41 1.0010 0.5656 0.2795 0.057 Uiso calc R 1 . .
N N43 0.7364(5) 0.2939(4) 0.2688(2) 0.0508(9) Uani d . 1 . .
C C41 0.8716(5) 0.5075(4) 0.3588(3) 0.0427(10) Uani d . 1 . .
C C42 0.8439(5) 0.3722(5) 0.2384(3) 0.0521(11) Uani d . 1 . .
H H42 0.8607 0.3417 0.1869 0.063 Uiso calc R 1 . .
C C43 0.7523(5) 0.3785(4) 0.3461(3) 0.0438(10) Uani d . 1 . .
C C44 0.6710(5) 0.3458(4) 0.4076(3) 0.0417(10) Uani d . 1 . .
C C45 0.7172(5) 0.4499(4) 0.4833(2) 0.0376(9) Uani d . 1 . .
C C46 0.8385(5) 0.5888(4) 0.4952(3) 0.0409(10) Uani d . 1 . .
C C47 0.9164(5) 0.6165(4) 0.4320(3) 0.0413(10) Uani d . 1 . .
C C51 0.5564(6) 0.2153(5) 0.3976(3) 0.0526(12) Uani d . 1 . .
H H51 0.5274 0.1475 0.3478 0.063 Uiso calc R 1 . .
C C52 0.4848(6) 0.1836(5) 0.4588(3) 0.0535(12) Uani d . 1 . .
H H52 0.4068 0.0963 0.4510 0.064 Uiso calc R 1 . .
C C53 0.5320(5) 0.2856(5) 0.5329(3) 0.0473(11) Uani d . 1 . .
C C54 0.6426(5) 0.4157(4) 0.5453(3) 0.0435(10) Uani d . 1 . .
H H54 0.6687 0.4823 0.5953 0.052 Uiso calc R 1 . .
C C61 1.0320(6) 0.7490(5) 0.4423(3) 0.0497(11) Uani d . 1 . .
H H61 1.0837 0.7659 0.4009 0.060 Uiso calc R 1 . .
C C62 1.0686(6) 0.8534(5) 0.5135(3) 0.0570(12) Uani d . 1 . .
H H62 1.1447 0.9413 0.5208 0.068 Uiso calc R 1 . .
C C63 0.9901(6) 0.8255(5) 0.5743(3) 0.0530(12) Uani d . 1 . .
C C64 0.8789(6) 0.6966(4) 0.5671(3) 0.0494(11) Uani d . 1 . .
H H64 0.8309 0.6814 0.6100 0.059 Uiso calc R 1 . .
Br Br23 -0.32947(6) -0.35521(6) -0.23022(3) 0.06483(18) Uani d . 1 . .
Br Br33 0.33555(9) 0.34459(6) -0.16606(4) 0.0839(2) Uani d . 1 . .
N N11 0.4763(5) 0.0408(4) 0.1674(2) 0.0502(9) Uani d . 1 . .
H H11 0.5635 0.1130 0.1911 0.060 Uiso calc R 1 . .
N N13 0.2838(5) -0.1650(4) 0.1477(2) 0.0537(10) Uani d . 1 . .
C C11 0.3671(5) 0.0154(4) 0.0922(2) 0.0413(9) Uani d . 1 . .
C C12 0.4198(7) -0.0696(5) 0.1969(3) 0.0591(13) Uani d . 1 . .
H H12 0.4728 -0.0776 0.2477 0.071 Uiso calc R 1 . .
C C13 0.2492(5) -0.1118(4) 0.0804(3) 0.0434(10) Uani d . 1 . .
C C14 0.1146(5) -0.1736(4) 0.0077(3) 0.0420(10) Uani d . 1 . .
C C15 0.1036(5) -0.0967(4) -0.0522(3) 0.0412(9) Uani d . 1 . .
C C16 0.2310(5) 0.0396(4) -0.0397(3) 0.0419(10) Uani d . 1 . .
C C17 0.3651(5) 0.0964(4) 0.0336(3) 0.0412(9) Uani d . 1 . .
C C21 -0.0044(6) -0.3057(4) -0.0068(3) 0.0491(11) Uani d . 1 . .
H H21 0.0052 -0.3570 0.0320 0.059 Uiso calc R 1 . .
C C22 -0.1333(6) -0.3602(5) -0.0765(3) 0.0542(12) Uani d . 1 . .
H H22 -0.2115 -0.4479 -0.0856 0.065 Uiso calc R 1 . .
C C23 -0.1457(5) -0.2820(4) -0.1340(3) 0.0461(10) Uani d . 1 . .
C C24 -0.0316(5) -0.1545(4) -0.1234(3) 0.0479(11) Uani d . 1 . .
H H24 -0.0431 -0.1056 -0.1634 0.057 Uiso calc R 1 . .
C C31 0.4856(6) 0.2249(4) 0.0442(3) 0.0476(11) Uani d . 1 . .
H H31 0.5726 0.2617 0.0924 0.057 Uiso calc R 1 . .
C C32 0.4793(6) 0.2983(5) -0.0141(3) 0.0534(12) Uani d . 1 . .
H H32 0.5611 0.3835 -0.0064 0.064 Uiso calc R 1 . .
C C33 0.3486(6) 0.2427(5) -0.0847(3) 0.0515(11) Uani d . 1 . .
C C34 0.2254(6) 0.1181(4) -0.0980(3) 0.0505(11) Uani d . 1 . .
H H34 0.1377 0.0853 -0.1459 0.061 Uiso calc R 1 . .
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'
Br Br -0.2901 2.4595 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
H1O O1 H2O . . 72(8) ?
C42 N41 C41 . . 107.2(4) ?
C42 N41 H41 . . 126.4 ?
C41 N41 H41 . . 126.4 ?
C42 N43 C43 . . 104.5(4) ?
N41 C41 C43 . . 105.8(4) ?
N41 C41 C47 . . 131.4(4) ?
C43 C41 C47 . . 122.8(4) ?
N43 C42 N41 . . 113.4(4) ?
N43 C42 H42 . . 123.3 ?
N41 C42 H42 . . 123.3 ?
C41 C43 N43 . . 109.2(4) ?
C41 C43 C44 . . 121.7(4) ?
N43 C43 C44 . . 129.1(4) ?
C51 C44 C45 . . 119.6(4) ?
C51 C44 C43 . . 122.8(4) ?
C45 C44 C43 . . 117.5(4) ?
C54 C45 C44 . . 117.6(4) ?
C54 C45 C46 . . 121.9(4) ?
C44 C45 C46 . . 120.5(4) ?
C64 C46 C47 . . 118.1(4) ?
C64 C46 C45 . . 122.1(4) ?
C47 C46 C45 . . 119.8(4) ?
C61 C47 C41 . . 121.9(4) ?
C61 C47 C46 . . 120.5(4) ?
C41 C47 C46 . . 117.6(4) ?
C52 C51 C44 . . 122.0(4) ?
C52 C51 H51 . . 119.0 ?
C44 C51 H51 . . 119.0 ?
C51 C52 C53 . . 117.9(4) ?
C51 C52 H52 . . 121.0 ?
C53 C52 H52 . . 121.0 ?
C54 C53 C52 . . 122.2(4) ?
C54 C53 Br53 . . 119.8(3) ?
C52 C53 Br53 . . 118.0(3) ?
C53 C54 C45 . . 120.6(4) ?
C53 C54 H54 . . 119.7 ?
C45 C54 H54 . . 119.7 ?
C62 C61 C47 . . 120.1(4) ?
C62 C61 H61 . . 119.9 ?
C47 C61 H61 . . 119.9 ?
C61 C62 C63 . . 118.8(4) ?
C61 C62 H62 . . 120.6 ?
C63 C62 H62 . . 120.6 ?
C64 C63 C62 . . 122.8(4) ?
C64 C63 Br63 . . 119.5(4) ?
C62 C63 Br63 . . 117.7(3) ?
C63 C64 C46 . . 119.7(4) ?
C63 C64 H64 . . 120.2 ?
C46 C64 H64 . . 120.2 ?
C12 N11 C11 . . 106.1(4) ?
C12 N11 H11 . . 126.9 ?
C11 N11 H11 . . 126.9 ?
C12 N13 C13 . . 103.8(4) ?
N11 C11 C13 . . 106.0(3) ?
N11 C11 C17 . . 130.7(4) ?
C13 C11 C17 . . 123.3(4) ?
N13 C12 N11 . . 114.0(4) ?
N13 C12 H12 . . 123.0 ?
N11 C12 H12 . . 123.0 ?
C11 C13 N13 . . 110.1(4) ?
C11 C13 C14 . . 122.1(4) ?
N13 C13 C14 . . 127.8(4) ?
C21 C14 C15 . . 119.6(4) ?
C21 C14 C13 . . 123.1(4) ?
C15 C14 C13 . . 117.3(4) ?
C24 C15 C14 . . 118.0(4) ?
C24 C15 C16 . . 121.4(4) ?
C14 C15 C16 . . 120.6(4) ?
C34 C16 C17 . . 117.6(4) ?
C34 C16 C15 . . 122.2(4) ?
C17 C16 C15 . . 120.2(4) ?
C31 C17 C16 . . 119.5(4) ?
C31 C17 C11 . . 123.9(4) ?
C16 C17 C11 . . 116.6(4) ?
C22 C21 C14 . . 121.4(4) ?
C22 C21 H21 . . 119.3 ?
C14 C21 H21 . . 119.3 ?
C21 C22 C23 . . 118.5(4) ?
C21 C22 H22 . . 120.7 ?
C23 C22 H22 . . 120.7 ?
C24 C23 C22 . . 122.3(4) ?
C24 C23 Br23 . . 118.9(3) ?
C22 C23 Br23 . . 118.8(3) ?
C23 C24 C15 . . 120.1(4) ?
C23 C24 H24 . . 119.9 ?
C15 C24 H24 . . 119.9 ?
C32 C31 C17 . . 121.8(4) ?
C32 C31 H31 . . 119.1 ?
C17 C31 H31 . . 119.1 ?
C31 C32 C33 . . 118.2(4) ?
C31 C32 H32 . . 120.9 ?
C33 C32 H32 . . 120.9 ?
C34 C33 C32 . . 122.6(4) ?
C34 C33 Br33 . . 118.5(3) ?
C32 C33 Br33 . . 118.9(3) ?
C33 C34 C16 . . 120.2(4) ?
C33 C34 H34 . . 119.9 ?
C16 C34 H34 . . 119.9 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 H1O . 0.91(10) ?
O1 H2O . 0.91(10) ?
Br53 C53 . 1.902(4) ?
Br63 C63 . 1.894(5) ?
N41 C42 . 1.339(6) ?
N41 C41 . 1.366(5) ?
N41 H41 . 0.8600 ?
N43 C42 . 1.314(6) ?
N43 C43 . 1.392(5) ?
C41 C43 . 1.387(6) ?
C41 C47 . 1.413(6) ?
C42 H42 . 0.9300 ?
C43 C44 . 1.421(6) ?
C44 C51 . 1.389(6) ?
C44 C45 . 1.418(6) ?
C45 C54 . 1.400(6) ?
C45 C46 . 1.472(5) ?
C46 C64 . 1.396(6) ?
C46 C47 . 1.419(6) ?
C47 C61 . 1.407(6) ?
C51 C52 . 1.369(6) ?
C51 H51 . 0.9300 ?
C52 C53 . 1.386(6) ?
C52 H52 . 0.9300 ?
C53 C54 . 1.364(6) ?
C54 H54 . 0.9300 ?
C61 C62 . 1.373(7) ?
C61 H61 . 0.9300 ?
C62 C63 . 1.383(7) ?
C62 H62 . 0.9300 ?
C63 C64 . 1.375(6) ?
C64 H64 . 0.9300 ?
Br23 C23 . 1.903(4) ?
Br33 C33 . 1.904(4) ?
N11 C12 . 1.343(6) ?
N11 C11 . 1.367(5) ?
N11 H11 . 0.8600 ?
N13 C12 . 1.307(6) ?
N13 C13 . 1.384(5) ?
C11 C13 . 1.371(5) ?
C11 C17 . 1.425(6) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.422(6) ?
C14 C21 . 1.403(5) ?
C14 C15 . 1.415(6) ?
C15 C24 . 1.405(6) ?
C15 C16 . 1.473(5) ?
C16 C34 . 1.403(6) ?
C16 C17 . 1.423(6) ?
C17 C31 . 1.394(6) ?
C21 C22 . 1.360(6) ?
C21 H21 . 0.9300 ?
C22 C23 . 1.391(6) ?
C22 H22 . 0.9300 ?
C23 C24 . 1.363(6) ?
C24 H24 . 0.9300 ?
C31 C32 . 1.367(6) ?
C31 H31 . 0.9300 ?
C32 C33 . 1.377(6) ?
C32 H32 . 0.9300 ?
C33 C34 . 1.369(6) ?
C34 H34 . 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N11 H11 N43 . 0.86 2.05 2.892(5) 165
N41 H41 O1 . 0.86 1.87 2.702(5) 164
O1 H2O N13 1_665 0.91(10) 1.83(10) 2.731(8) 172(13)
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C42 N41 C41 C43 . . . . -0.4(5) ?
C42 N41 C41 C47 . . . . 179.6(4) ?
C43 N43 C42 N41 . . . . -0.5(5) ?
C41 N41 C42 N43 . . . . 0.6(5) ?
N41 C41 C43 N43 . . . . 0.1(5) ?
C47 C41 C43 N43 . . . . -179.9(4) ?
N41 C41 C43 C44 . . . . 177.8(4) ?
C47 C41 C43 C44 . . . . -2.2(6) ?
C42 N43 C43 C41 . . . . 0.2(5) ?
C42 N43 C43 C44 . . . . -177.3(4) ?
C41 C43 C44 C51 . . . . -177.3(4) ?
N43 C43 C44 C51 . . . . -0.1(7) ?
C41 C43 C44 C45 . . . . -0.5(6) ?
N43 C43 C44 C45 . . . . 176.7(4) ?
C51 C44 C45 C54 . . . . -0.4(6) ?
C43 C44 C45 C54 . . . . -177.3(4) ?
C51 C44 C45 C46 . . . . 180.0(4) ?
C43 C44 C45 C46 . . . . 3.1(6) ?
C54 C45 C46 C64 . . . . -3.5(6) ?
C44 C45 C46 C64 . . . . 176.0(4) ?
C54 C45 C46 C47 . . . . 177.2(4) ?
C44 C45 C46 C47 . . . . -3.2(6) ?
N41 C41 C47 C61 . . . . 3.0(7) ?
C43 C41 C47 C61 . . . . -177.0(4) ?
N41 C41 C47 C46 . . . . -177.9(4) ?
C43 C41 C47 C46 . . . . 2.1(6) ?
C64 C46 C47 C61 . . . . 0.4(6) ?
C45 C46 C47 C61 . . . . 179.7(4) ?
C64 C46 C47 C41 . . . . -178.7(4) ?
C45 C46 C47 C41 . . . . 0.6(6) ?
C45 C44 C51 C52 . . . . 0.4(7) ?
C43 C44 C51 C52 . . . . 177.1(4) ?
C44 C51 C52 C53 . . . . -1.0(7) ?
C51 C52 C53 C54 . . . . 1.8(7) ?
C51 C52 C53 Br53 . . . . 179.4(4) ?
C52 C53 C54 C45 . . . . -1.9(7) ?
Br53 C53 C54 C45 . . . . -179.5(3) ?
C44 C45 C54 C53 . . . . 1.1(6) ?
C46 C45 C54 C53 . . . . -179.3(4) ?
C41 C47 C61 C62 . . . . 178.2(4) ?
C46 C47 C61 C62 . . . . -0.8(6) ?
C47 C61 C62 C63 . . . . 0.0(7) ?
C61 C62 C63 C64 . . . . 1.2(7) ?
C61 C62 C63 Br63 . . . . -179.4(3) ?
C62 C63 C64 C46 . . . . -1.6(7) ?
Br63 C63 C64 C46 . . . . 179.0(3) ?
C47 C46 C64 C63 . . . . 0.7(6) ?
C45 C46 C64 C63 . . . . -178.5(4) ?
C12 N11 C11 C13 . . . . -0.2(5) ?
C12 N11 C11 C17 . . . . -179.9(5) ?
C13 N13 C12 N11 . . . . 0.0(6) ?
C11 N11 C12 N13 . . . . 0.1(6) ?
N11 C11 C13 N13 . . . . 0.2(5) ?
C17 C11 C13 N13 . . . . 180.0(4) ?
N11 C11 C13 C14 . . . . -179.5(4) ?
C17 C11 C13 C14 . . . . 0.3(7) ?
C12 N13 C13 C11 . . . . -0.2(5) ?
C12 N13 C13 C14 . . . . 179.6(5) ?
C11 C13 C14 C21 . . . . 177.9(4) ?
N13 C13 C14 C21 . . . . -1.8(7) ?
C11 C13 C14 C15 . . . . -1.6(6) ?
N13 C13 C14 C15 . . . . 178.7(4) ?
C21 C14 C15 C24 . . . . 2.3(6) ?
C13 C14 C15 C24 . . . . -178.2(4) ?
C21 C14 C15 C16 . . . . -177.6(4) ?
C13 C14 C15 C16 . . . . 1.9(6) ?
C24 C15 C16 C34 . . . . -0.5(6) ?
C14 C15 C16 C34 . . . . 179.3(4) ?
C24 C15 C16 C17 . . . . 179.1(4) ?
C14 C15 C16 C17 . . . . -1.0(6) ?
C34 C16 C17 C31 . . . . -0.8(6) ?
C15 C16 C17 C31 . . . . 179.5(4) ?
C34 C16 C17 C11 . . . . 179.4(4) ?
C15 C16 C17 C11 . . . . -0.3(6) ?
N11 C11 C17 C31 . . . . 0.7(7) ?
C13 C11 C17 C31 . . . . -179.1(4) ?
N11 C11 C17 C16 . . . . -179.6(4) ?
C13 C11 C17 C16 . . . . 0.7(6) ?
C15 C14 C21 C22 . . . . -1.8(7) ?
C13 C14 C21 C22 . . . . 178.8(4) ?
C14 C21 C22 C23 . . . . 0.0(7) ?
C21 C22 C23 C24 . . . . 1.3(7) ?
C21 C22 C23 Br23 . . . . -178.3(3) ?
C22 C23 C24 C15 . . . . -0.8(7) ?
Br23 C23 C24 C15 . . . . 178.8(3) ?
C14 C15 C24 C23 . . . . -1.1(6) ?
C16 C15 C24 C23 . . . . 178.8(4) ?
C16 C17 C31 C32 . . . . -0.3(7) ?
C11 C17 C31 C32 . . . . 179.4(4) ?
C17 C31 C32 C33 . . . . 0.6(7) ?
C31 C32 C33 C34 . . . . 0.4(7) ?
C31 C32 C33 Br33 . . . . 179.1(4) ?
C32 C33 C34 C16 . . . . -1.6(7) ?
Br33 C33 C34 C16 . . . . 179.7(3) ?
C17 C16 C34 C33 . . . . 1.8(6) ?
C15 C16 C34 C33 . . . . -178.5(4) ?
