#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/07/2230742.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_2230742
loop_
_publ_author_name
'Haque, Rosenani A.'
'Iqbal, Muhammad Adnan'
'Hemamalini, Madhukar'
'Fun, Hoong-Kun'
_publ_section_title
;
 3,3'-[1,2-Phenylenebis(methylene)]bis(1-heptylbenzimidazolium)
 dibromide monohydrate
;
_journal_coeditor_code           IS2732
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1814
_journal_page_last               o1815
_journal_paper_doi               10.1107/S1600536811023476
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C36 H48 N4 2+, 2Br -, H2 O'
_chemical_formula_moiety         'C36 H48 N4 2+, 2(Br -), H2 O'
_chemical_formula_sum            'C36 H50 Br2 N4 O'
_chemical_formula_weight         714.62
_chemical_name_systematic
;
3,3'-[1,2-Phenylenebis(methylene)]bis(1-heptylbenzimidazolium) dibromide
monohydrate
;
_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           SHELXL-97
_cell_angle_alpha                115.7050(10)
_cell_angle_beta                 105.3800(10)
_cell_angle_gamma                91.9460(10)
_cell_formula_units_Z            2
_cell_length_a                   8.84940(10)
_cell_length_b                   14.7170(3)
_cell_length_c                   16.0838(2)
_cell_measurement_reflns_used    9922
_cell_measurement_temperature    100.0(10)
_cell_measurement_theta_max      33.74
_cell_measurement_theta_min      2.60
_cell_volume                     1792.85(5)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0(10)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type
;
Bruker SMART APEXII CCD area-detector
;
_diffrn_measurement_method       'φ and ω'
_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  0.0273
_diffrn_reflns_av_sigmaI/netI    0.0334
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            50860
_diffrn_reflns_theta_full        32.50
_diffrn_reflns_theta_max         32.50
_diffrn_reflns_theta_min         1.48
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.293
_exptl_absorpt_correction_T_max  0.7147
_exptl_absorpt_correction_T_min  0.4691
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.835
_refine_diff_density_min         -0.746
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     442
_refine_ls_number_reflns         12945
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0315
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0359P)²+0.6181P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0700
_refine_ls_wR_factor_ref         0.0770
_reflns_number_gt                10091
_reflns_number_total             12945
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is2732.cif
_cod_data_source_block           I
_cod_original_cell_volume        1792.83(5)
_cod_database_code               2230742
_cod_database_fobs_code          2230742
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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.365462(16) 0.228743(11) 0.219134(10) 0.02173(4) Uani d . 1 1 . .
Br Br2 0.031239(16) 0.512483(11) 0.193441(10) 0.02124(4) Uani d . 1 1 . .
N N1 0.48319(13) 0.66074(9) 0.94225(8) 0.0168(2) Uani d . 1 1 . .
N N2 0.72144(13) 0.65150(9) 1.01988(8) 0.0172(2) Uani d . 1 1 . .
N N3 0.07774(13) 0.69630(9) 0.68277(8) 0.0178(2) Uani d . 1 1 . .
N N4 0.19471(14) 0.67552(10) 0.57302(9) 0.0198(2) Uani d . 1 1 A .
C C1 0.63655(16) 0.66612(10) 0.94634(10) 0.0171(2) Uani d . 1 1 . .
H H1A 0.6787 0.6786 0.9030 0.021 Uiso calc R 1 1 . .
C C2 0.61934(16) 0.63548(10) 1.06701(10) 0.0167(2) Uani d . 1 1 . .
C C3 0.64670(17) 0.61359(11) 1.14536(10) 0.0193(3) Uani d . 1 1 . .
H H3A 0.7500 0.6096 1.1792 0.023 Uiso calc R 1 1 . .
C C4 0.51353(18) 0.59803(11) 1.17085(10) 0.0207(3) Uani d . 1 1 . .
H H4A 0.5262 0.5831 1.2239 0.025 Uiso calc R 1 1 . .
C C5 0.36033(18) 0.60365(11) 1.12058(11) 0.0215(3) Uani d . 1 1 . .
H H5A 0.2727 0.5921 1.1405 0.026 Uiso calc R 1 1 . .
C C6 0.33375(16) 0.62550(11) 1.04280(10) 0.0193(3) Uani d . 1 1 . .
H H6A 0.2306 0.6294 1.0088 0.023 Uiso calc R 1 1 . .
C C7 0.46771(16) 0.64135(10) 1.01748(10) 0.0166(2) Uani d . 1 1 . .
C C8 0.35503(16) 0.67445(11) 0.87201(10) 0.0187(3) Uani d . 1 1 . .
H H8A 0.2604 0.6221 0.8496 0.022 Uiso calc R 1 1 . .
H H8B 0.3889 0.6635 0.8149 0.022 Uiso calc R 1 1 . .
C C9 0.30936(16) 0.77994(11) 0.91357(10) 0.0177(3) Uani d . 1 1 . .
C C10 0.40829(17) 0.86003(11) 0.99982(11) 0.0220(3) Uani d . 1 1 . .
H H10A 0.5053 0.8482 1.0332 0.026 Uiso calc R 1 1 . .
C C11 0.36713(19) 0.95694(12) 1.03770(11) 0.0252(3) Uani d . 1 1 . .
H H11A 0.4355 1.0105 1.0967 0.030 Uiso calc R 1 1 . .
C C12 0.2263(2) 0.97520(12) 0.98931(11) 0.0266(3) Uani d . 1 1 . .
H H12A 0.1980 1.0413 1.0148 0.032 Uiso calc R 1 1 . .
C C13 0.12706(19) 0.89630(13) 0.90350(11) 0.0253(3) Uani d . 1 1 . .
H H13A 0.0305 0.9089 0.8705 0.030 Uiso calc R 1 1 . .
C C14 0.16660(16) 0.79853(11) 0.86476(10) 0.0193(3) Uani d . 1 1 . .
C C15 0.04692(16) 0.71575(12) 0.77466(10) 0.0204(3) Uani d . 1 1 . .
H H15A 0.0452 0.6514 0.7803 0.025 Uiso calc R 1 1 . .
H H15B -0.0599 0.7348 0.7715 0.025 Uiso calc R 1 1 . .
C C16 -0.03893(16) 0.64533(11) 0.59265(10) 0.0183(3) Uani d . 1 1 . .
C C17 -0.20136(17) 0.61256(12) 0.56824(11) 0.0215(3) Uani d . 1 1 . .
H H17A -0.2515 0.6215 0.6160 0.026 Uiso calc R 1 1 . .
C C18 -0.28532(18) 0.56616(12) 0.46997(11) 0.0250(3) Uani d . 1 1 . .
H H18A -0.3966 0.5430 0.4497 0.030 Uiso calc R 1 1 . .
C C19 -0.21027(19) 0.55241(12) 0.39959(11) 0.0261(3) Uani d . 1 1 . .
H H19A -0.2724 0.5198 0.3330 0.031 Uiso calc R 1 1 . .
C C20 -0.04885(19) 0.58480(12) 0.42390(11) 0.0246(3) Uani d . 1 1 . .
H H20A 0.0016 0.5754 0.3761 0.029 Uiso calc R 1 1 . .
C C21 0.03504(17) 0.63207(11) 0.52276(10) 0.0197(3) Uani d . 1 1 . .
C C22 0.21526(16) 0.71327(11) 0.66812(10) 0.0190(3) Uani d . 1 1 . .
H H22A 0.3135 0.7472 0.7180 0.023 Uiso calc R 1 1 . .
C C23 0.89380(16) 0.64783(11) 1.04495(10) 0.0199(3) Uani d . 1 1 . .
H H23A 0.9285 0.6320 0.9872 0.024 Uiso calc R 1 1 . .
H H23B 0.9132 0.5921 1.0632 0.024 Uiso calc R 1 1 . .
C C24 0.99196(17) 0.74804(11) 1.12807(11) 0.0217(3) Uani d . 1 1 . .
H H24A 1.1005 0.7363 1.1530 0.026 Uiso calc R 1 1 . .
H H24B 0.9441 0.7700 1.1814 0.026 Uiso calc R 1 1 . .
C C25 1.0042(2) 0.83405(12) 1.10038(12) 0.0279(3) Uani d . 1 1 . .
H H25A 0.8967 0.8498 1.0803 0.033 Uiso calc R 1 1 . .
H H25B 1.0449 0.8106 1.0440 0.033 Uiso calc R 1 1 . .
C C26 1.1138(2) 0.93188(13) 1.18354(13) 0.0312(4) Uani d . 1 1 . .
H H26A 1.2184 0.9146 1.2074 0.037 Uiso calc R 1 1 . .
H H26B 1.1310 0.9804 1.1580 0.037 Uiso calc R 1 1 . .
C C27 1.0495(2) 0.98436(13) 1.26812(13) 0.0318(4) Uani d . 1 1 . .
H H27A 1.0368 0.9369 1.2954 0.038 Uiso calc R 1 1 . .
H H27B 0.9428 0.9987 1.2436 0.038 Uiso calc R 1 1 . .
C C28 1.1542(3) 1.08388(15) 1.34891(15) 0.0474(4) Uani d . 1 1 . .
H H28A 1.1636 1.1328 1.3227 0.057 Uiso calc R 1 1 . .
H H28B 1.2621 1.0704 1.3724 0.057 Uiso calc R 1 1 . .
C C29 1.0880(3) 1.13208(15) 1.43403(15) 0.0474(4) Uani d . 1 1 . .
H H29A 1.1598 1.1953 1.4847 0.071 Uiso calc R 1 1 . .
H H29B 1.0790 1.0841 1.4605 0.071 Uiso calc R 1 1 . .
H H29C 0.9827 1.1478 1.4116 0.071 Uiso calc R 1 1 . .
C C30 0.31844(18) 0.68129(12) 0.52875(11) 0.0237(3) Uani d . 1 1 . .
H H30A 0.3231 0.6112 0.4817 0.028 Uiso calc PR 0.474(5) 1 A 1
H H30B 0.4229 0.7092 0.5801 0.028 Uiso calc PR 0.474(5) 1 A 1
H H30C 0.3035 0.6192 0.4701 0.028 Uiso d PR 0.526(5) 1 A 2
H H30D 0.4214 0.6897 0.5729 0.028 Uiso d PR 0.526(5) 1 A 2
C C31 0.2912(8) 0.7454(5) 0.4784(4) 0.0235(11) Uani d PD 0.474(5) 1 A 1
H H31A 0.2774 0.8131 0.5252 0.028 Uiso calc PR 0.474(5) 1 A 1
H H31D 0.1887 0.7142 0.4256 0.028 Uiso calc PR 0.474(5) 1 A 1
C C32 0.4121(14) 0.7637(9) 0.4352(8) 0.0239(12) Uani d PD 0.474(5) 1 A 1
H H32A 0.3838 0.7084 0.3677 0.029 Uiso calc PR 0.474(5) 1 A 1
H H32D 0.5159 0.7554 0.4712 0.029 Uiso calc PR 0.474(5) 1 A 1
C C33 0.4379(5) 0.8674(3) 0.4321(3) 0.0283(9) Uani d PD 0.474(5) 1 A 1
H H33A 0.3348 0.8910 0.4194 0.034 Uiso calc PR 0.474(5) 1 A 1
H H33B 0.5095 0.9198 0.4956 0.034 Uiso calc PR 0.474(5) 1 A 1
C C34 0.5109(7) 0.8542(6) 0.3522(5) 0.0284(13) Uani d PD 0.474(5) 1 A 1
H H34A 0.6021 0.8179 0.3584 0.034 Uiso calc PR 0.474(5) 1 A 1
H H34B 0.4308 0.8102 0.2884 0.034 Uiso calc PR 0.474(5) 1 A 1
C C35 0.5674(5) 0.9528(3) 0.3533(3) 0.0302(9) Uani d PD 0.474(5) 1 A 1
H H35A 0.4821 0.9949 0.3581 0.036 Uiso calc PR 0.474(5) 1 A 1
H H35B 0.6609 0.9917 0.4114 0.036 Uiso calc PR 0.474(5) 1 A 1
C C36 0.6121(7) 0.9350(6) 0.2638(4) 0.0435(14) Uani d PD 0.474(5) 1 A 1
H H36A 0.6544 1.0007 0.2699 0.065 Uiso calc PR 0.474(5) 1 A 1
H H36B 0.5177 0.9018 0.2064 0.065 Uiso calc PR 0.474(5) 1 A 1
H H36C 0.6932 0.8909 0.2571 0.065 Uiso calc PR 0.474(5) 1 A 1
C C31X 0.3150(8) 0.7765(4) 0.5075(4) 0.0293(11) Uani d PD 0.526(5) 1 A 2
H H31B 0.2075 0.7748 0.4674 0.035 Uiso calc PR 0.526(5) 1 A 2
H H31C 0.3463 0.8414 0.5687 0.035 Uiso calc PR 0.526(5) 1 A 2
C C32X 0.4359(12) 0.7661(8) 0.4522(7) 0.0239(12) Uani d PD 0.526(5) 1 A 2
H H32B 0.4350 0.6924 0.4124 0.029 Uiso calc PR 0.526(5) 1 A 2
H H32C 0.5435 0.7961 0.5000 0.029 Uiso calc PR 0.526(5) 1 A 2
C C33X 0.4057(4) 0.8177(3) 0.3857(3) 0.0265(8) Uani d PD 0.526(5) 1 A 2
H H33C 0.3278 0.7700 0.3223 0.032 Uiso calc PR 0.526(5) 1 A 2
H H33D 0.3582 0.8792 0.4150 0.032 Uiso calc PR 0.526(5) 1 A 2
C C34X 0.5560(6) 0.8489(5) 0.3687(5) 0.0227(10) Uani d PD 0.526(5) 1 A 2
H H34C 0.6078 0.7883 0.3439 0.027 Uiso calc PR 0.526(5) 1 A 2
H H34D 0.6308 0.9005 0.4314 0.027 Uiso calc PR 0.526(5) 1 A 2
C C35X 0.5249(4) 0.8934(3) 0.2968(3) 0.0292(8) Uani d PD 0.526(5) 1 A 2
H H35C 0.4514 0.8415 0.2337 0.035 Uiso calc PR 0.526(5) 1 A 2
H H35D 0.4720 0.9535 0.3210 0.035 Uiso calc PR 0.526(5) 1 A 2
C C36X 0.6762(6) 0.9258(4) 0.2811(4) 0.0358(10) Uani d PD 0.526(5) 1 A 2
H H36D 0.6505 0.9590 0.2391 0.054 Uiso calc PR 0.526(5) 1 A 2
H H36E 0.7231 0.8653 0.2503 0.054 Uiso calc PR 0.526(5) 1 A 2
H H36F 0.7524 0.9738 0.3439 0.054 Uiso calc PR 0.526(5) 1 A 2
O O1W 0.39216(15) 0.47948(11) 0.29323(9) 0.0324(3) Uani d . 1 1 . .
H H1W1 0.380(3) 0.4177(19) 0.2809(17) 0.050(7) Uiso d . 1 1 . .
H H2W1 0.307(3) 0.4896(18) 0.2719(17) 0.048(7) Uiso d . 1 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C7 . . 108.14(11) ?
C1 N1 C8 . . 125.77(12) ?
C7 N1 C8 . . 126.08(11) ?
C1 N2 C2 . . 108.59(11) ?
C1 N2 C23 . . 125.85(12) ?
C2 N2 C23 . . 125.50(12) ?
C22 N3 C16 . . 108.14(11) ?
C22 N3 C15 . . 128.98(12) ?
C16 N3 C15 . . 122.61(11) ?
C22 N4 C21 . . 108.35(12) ?
C22 N4 C30 . . 125.98(12) ?
C21 N4 C30 . . 125.65(12) ?
N2 C1 N1 . . 110.19(12) ?
N2 C1 H1A . . 124.9 ?
N1 C1 H1A . . 124.9 ?
C7 C2 C3 . . 122.01(13) ?
C7 C2 N2 . . 106.38(12) ?
C3 C2 N2 . . 131.57(13) ?
C4 C3 C2 . . 115.83(13) ?
C4 C3 H3A . . 122.1 ?
C2 C3 H3A . . 122.1 ?
C3 C4 C5 . . 122.12(13) ?
C3 C4 H4A . . 118.9 ?
C5 C4 H4A . . 118.9 ?
C6 C5 C4 . . 121.84(13) ?
C6 C5 H5A . . 119.1 ?
C4 C5 H5A . . 119.1 ?
C5 C6 C7 . . 115.94(13) ?
C5 C6 H6A . . 122.0 ?
C7 C6 H6A . . 122.0 ?
C2 C7 C6 . . 122.25(13) ?
C2 C7 N1 . . 106.71(11) ?
C6 C7 N1 . . 130.99(13) ?
N1 C8 C9 . . 112.83(11) ?
N1 C8 H8A . . 109.0 ?
C9 C8 H8A . . 109.0 ?
N1 C8 H8B . . 109.0 ?
C9 C8 H8B . . 109.0 ?
H8A C8 H8B . . 107.8 ?
C10 C9 C14 . . 118.88(13) ?
C10 C9 C8 . . 120.99(13) ?
C14 C9 C8 . . 120.13(12) ?
C11 C10 C9 . . 121.08(14) ?
C11 C10 H10A . . 119.5 ?
C9 C10 H10A . . 119.5 ?
C12 C11 C10 . . 119.96(14) ?
C12 C11 H11A . . 120.0 ?
C10 C11 H11A . . 120.0 ?
C11 C12 C13 . . 119.53(15) ?
C11 C12 H12A . . 120.2 ?
C13 C12 H12A . . 120.2 ?
C12 C13 C14 . . 121.15(14) ?
C12 C13 H13A . . 119.4 ?
C14 C13 H13A . . 119.4 ?
C13 C14 C9 . . 119.41(13) ?
C13 C14 C15 . . 117.53(13) ?
C9 C14 C15 . . 122.95(13) ?
N3 C15 C14 . . 114.66(11) ?
N3 C15 H15A . . 108.6 ?
C14 C15 H15A . . 108.6 ?
N3 C15 H15B . . 108.6 ?
C14 C15 H15B . . 108.6 ?
H15A C15 H15B . . 107.6 ?
C21 C16 N3 . . 106.94(12) ?
C21 C16 C17 . . 122.16(13) ?
N3 C16 C17 . . 130.88(13) ?
C18 C17 C16 . . 115.95(14) ?
C18 C17 H17A . . 122.0 ?
C16 C17 H17A . . 122.0 ?
C17 C18 C19 . . 121.77(14) ?
C17 C18 H18A . . 119.1 ?
C19 C18 H18A . . 119.1 ?
C20 C19 C18 . . 122.23(14) ?
C20 C19 H19A . . 118.9 ?
C18 C19 H19A . . 118.9 ?
C19 C20 C21 . . 115.87(14) ?
C19 C20 H20A . . 122.1 ?
C21 C20 H20A . . 122.1 ?
C16 C21 C20 . . 122.01(13) ?
C16 C21 N4 . . 106.38(12) ?
C20 C21 N4 . . 131.60(14) ?
N3 C22 N4 . . 110.19(12) ?
N3 C22 H22A . . 124.9 ?
N4 C22 H22A . . 124.9 ?
N2 C23 C24 . . 112.21(12) ?
N2 C23 H23A . . 109.2 ?
C24 C23 H23A . . 109.2 ?
N2 C23 H23B . . 109.2 ?
C24 C23 H23B . . 109.2 ?
H23A C23 H23B . . 107.9 ?
C23 C24 C25 . . 113.95(13) ?
C23 C24 H24A . . 108.8 ?
C25 C24 H24A . . 108.8 ?
C23 C24 H24B . . 108.8 ?
C25 C24 H24B . . 108.8 ?
H24A C24 H24B . . 107.7 ?
C24 C25 C26 . . 112.82(14) ?
C24 C25 H25A . . 109.0 ?
C26 C25 H25A . . 109.0 ?
C24 C25 H25B . . 109.0 ?
C26 C25 H25B . . 109.0 ?
H25A C25 H25B . . 107.8 ?
C27 C26 C25 . . 113.75(14) ?
C27 C26 H26A . . 108.8 ?
C25 C26 H26A . . 108.8 ?
C27 C26 H26B . . 108.8 ?
C25 C26 H26B . . 108.8 ?
H26A C26 H26B . . 107.7 ?
C26 C27 C28 . . 114.01(16) ?
C26 C27 H27A . . 108.8 ?
C28 C27 H27A . . 108.8 ?
C26 C27 H27B . . 108.8 ?
C28 C27 H27B . . 108.8 ?
H27A C27 H27B . . 107.6 ?
C27 C28 C29 . . 112.23(19) ?
C27 C28 H28A . . 109.2 ?
C29 C28 H28A . . 109.2 ?
C27 C28 H28B . . 109.2 ?
C29 C28 H28B . . 109.2 ?
H28A C28 H28B . . 107.9 ?
C28 C29 H29A . . 109.5 ?
C28 C29 H29B . . 109.5 ?
H29A C29 H29B . . 109.5 ?
C28 C29 H29C . . 109.5 ?
H29A C29 H29C . . 109.5 ?
H29B C29 H29C . . 109.5 ?
N4 C30 C31 . . 113.6(3) ?
N4 C30 C31X . . 110.5(3) ?
N4 C30 H30A . . 108.9 ?
C31 C30 H30A . . 108.9 ?
N4 C30 H30B . . 108.9 ?
C31 C30 H30B . . 108.9 ?
H30A C30 H30B . . 107.7 ?
N4 C30 H30C . . 110.1 ?
C31 C30 H30C . . 93.8 ?
C31X C30 H30C . . 110.5 ?
H30B C30 H30C . . 121.1 ?
N4 C30 H30D . . 109.5 ?
C31 C30 H30D . . 120.1 ?
C31X C30 H30D . . 107.8 ?
H30A C30 H30D . . 93.7 ?
H30C C30 H30D . . 108.3 ?
C30 C31 C32 . . 119.6(6) ?
C30 C31 H31A . . 107.4 ?
C32 C31 H31A . . 107.4 ?
C30 C31 H31D . . 107.4 ?
C32 C31 H31D . . 107.4 ?
H31A C31 H31D . . 106.9 ?
C31 C32 C33 . . 119.7(9) ?
C31 C32 H32A . . 107.4 ?
C33 C32 H32A . . 107.4 ?
C31 C32 H32D . . 107.4 ?
C33 C32 H32D . . 107.4 ?
H32A C32 H32D . . 106.9 ?
C34 C33 C32 . . 110.0(6) ?
C34 C33 H33A . . 109.7 ?
C32 C33 H33A . . 109.7 ?
C34 C33 H33B . . 109.7 ?
C32 C33 H33B . . 109.7 ?
H33A C33 H33B . . 108.2 ?
C35 C34 C33 . . 114.8(5) ?
C35 C34 H34A . . 108.6 ?
C33 C34 H34A . . 108.6 ?
C35 C34 H34B . . 108.6 ?
C33 C34 H34B . . 108.6 ?
H34A C34 H34B . . 107.5 ?
C36 C35 C34 . . 112.6(5) ?
C36 C35 H35A . . 109.1 ?
C34 C35 H35A . . 109.1 ?
C36 C35 H35B . . 109.1 ?
C34 C35 H35B . . 109.1 ?
H35A C35 H35B . . 107.8 ?
C32X C31X C30 . . 104.7(5) ?
C32X C31X H31B . . 110.8 ?
C30 C31X H31B . . 110.8 ?
C32X C31X H31C . . 110.8 ?
C30 C31X H31C . . 110.8 ?
H31B C31X H31C . . 108.9 ?
C31X C32X C33X . . 114.6(7) ?
C31X C32X H32B . . 108.6 ?
C33X C32X H32B . . 108.6 ?
C31X C32X H32C . . 108.6 ?
C33X C32X H32C . . 108.6 ?
H32B C32X H32C . . 107.6 ?
C34X C33X C32X . . 113.1(5) ?
C34X C33X H33C . . 109.0 ?
C32X C33X H33C . . 109.0 ?
C34X C33X H33D . . 109.0 ?
C32X C33X H33D . . 109.0 ?
H33C C33X H33D . . 107.8 ?
C33X C34X C35X . . 113.3(4) ?
C33X C34X H34C . . 108.9 ?
C35X C34X H34C . . 108.9 ?
C33X C34X H34D . . 108.9 ?
C35X C34X H34D . . 108.9 ?
H34C C34X H34D . . 107.7 ?
C36X C35X C34X . . 113.0(4) ?
C36X C35X H35C . . 109.0 ?
C34X C35X H35C . . 109.0 ?
C36X C35X H35D . . 109.0 ?
C34X C35X H35D . . 109.0 ?
H35C C35X H35D . . 107.8 ?
C35X C36X H36D . . 109.5 ?
C35X C36X H36E . . 109.5 ?
H36D C36X H36E . . 109.5 ?
C35X C36X H36F . . 109.5 ?
H36D C36X H36F . . 109.5 ?
H36E C36X H36F . . 109.5 ?
H1W1 O1W H2W1 . . 106(2) ?
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
N1 C1 . 1.3391(17) ?
N1 C7 . 1.3961(17) ?
N1 C8 . 1.4618(18) ?
N2 C1 . 1.3304(18) ?
N2 C2 . 1.3965(17) ?
N2 C23 . 1.4799(18) ?
N3 C22 . 1.3348(17) ?
N3 C16 . 1.3928(17) ?
N3 C15 . 1.4808(18) ?
N4 C22 . 1.3377(18) ?
N4 C21 . 1.3940(18) ?
N4 C30 . 1.4740(18) ?
C1 H1A . 0.9500 ?
C2 C7 . 1.3940(19) ?
C2 C3 . 1.3949(19) ?
C3 C4 . 1.389(2) ?
C3 H3A . 0.9500 ?
C4 C5 . 1.408(2) ?
C4 H4A . 0.9500 ?
C5 C6 . 1.386(2) ?
C5 H5A . 0.9500 ?
C6 C7 . 1.3947(19) ?
C6 H6A . 0.9500 ?
C8 C9 . 1.519(2) ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
C9 C10 . 1.3955(19) ?
C9 C14 . 1.404(2) ?
C10 C11 . 1.392(2) ?
C10 H10A . 0.9500 ?
C11 C12 . 1.386(2) ?
C11 H11A . 0.9500 ?
C12 C13 . 1.386(2) ?
C12 H12A . 0.9500 ?
C13 C14 . 1.398(2) ?
C13 H13A . 0.9500 ?
C14 C15 . 1.507(2) ?
C15 H15A . 0.9900 ?
C15 H15B . 0.9900 ?
C16 C21 . 1.392(2) ?
C16 C17 . 1.3936(19) ?
C17 C18 . 1.387(2) ?
C17 H17A . 0.9500 ?
C18 C19 . 1.404(2) ?
C18 H18A . 0.9500 ?
C19 C20 . 1.384(2) ?
C19 H19A . 0.9500 ?
C20 C21 . 1.394(2) ?
C20 H20A . 0.9500 ?
C22 H22A . 0.9500 ?
C23 C24 . 1.518(2) ?
C23 H23A . 0.9900 ?
C23 H23B . 0.9900 ?
C24 C25 . 1.522(2) ?
C24 H24A . 0.9900 ?
C24 H24B . 0.9900 ?
C25 C26 . 1.533(2) ?
C25 H25A . 0.9900 ?
C25 H25B . 0.9900 ?
C26 C27 . 1.517(2) ?
C26 H26A . 0.9900 ?
C26 H26B . 0.9900 ?
C27 C28 . 1.520(3) ?
C27 H27A . 0.9900 ?
C27 H27B . 0.9900 ?
C28 C29 . 1.527(3) ?
C28 H28A . 0.9900 ?
C28 H28B . 0.9900 ?
C29 H29A . 0.9800 ?
C29 H29B . 0.9800 ?
C29 H29C . 0.9800 ?
C30 C31 . 1.475(8) ?
C30 C31X . 1.580(7) ?
C30 H30A . 0.9900 ?
C30 H30B . 0.9900 ?
C30 H30C . 0.9600 ?
C30 H30D . 0.9600 ?
C31 C32 . 1.496(9) ?
C31 H31A . 0.9900 ?
C31 H31D . 0.9900 ?
C32 C33 . 1.560(10) ?
C32 H32A . 0.9900 ?
C32 H32D . 0.9900 ?
C33 C34 . 1.529(7) ?
C33 H33A . 0.9900 ?
C33 H33B . 0.9900 ?
C34 C35 . 1.511(7) ?
C34 H34A . 0.9900 ?
C34 H34B . 0.9900 ?
C35 C36 . 1.508(6) ?
C35 H35A . 0.9900 ?
C35 H35B . 0.9900 ?
C36 H36A . 0.9800 ?
C36 H36B . 0.9800 ?
C36 H36C . 0.9800 ?
C31X C32X . 1.534(9) ?
C31X H31B . 0.9900 ?
C31X H31C . 0.9900 ?
C32X C33X . 1.536(8) ?
C32X H32B . 0.9900 ?
C32X H32C . 0.9900 ?
C33X C34X . 1.522(6) ?
C33X H33C . 0.9900 ?
C33X H33D . 0.9900 ?
C34X C35X . 1.529(6) ?
C34X H34C . 0.9900 ?
C34X H34D . 0.9900 ?
C35X C36X . 1.524(5) ?
C35X H35C . 0.9900 ?
C35X H35D . 0.9900 ?
C36X H36D . 0.9800 ?
C36X H36E . 0.9800 ?
C36X H36F . 0.9800 ?
O1W H1W1 . 0.84(2) ?
O1W H2W1 . 0.79(3) ?
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
_geom_hbond_publ_flag
O1W H1W1 Br1 . 0.84(3) 2.50(3) 3.3271(17) 169(2) yes
O1W H2W1 Br2 . 0.79(3) 2.54(3) 3.3280(14) 177(3) yes
C1 H1A Br1 2_666 0.95 2.80 3.6093(15) 144 yes
C3 H3A Br2 1_656 0.95 2.92 3.7866(16) 153 yes
C5 H5A Br2 1_556 0.95 2.89 3.8162(17) 167 yes
C8 H8A Br2 2_566 0.99 2.93 3.9117(16) 172 yes
C15 H15A Br2 2_566 0.99 2.72 3.6809(19) 165 yes
C15 H15B Br1 2_566 0.99 2.80 3.7842(15) 170 yes
C18 H18A O1W 1_455 0.95 2.46 3.187(2) 133 yes
C20 H20A Br2 . 0.95 2.76 3.6602(16) 158 yes
C22 H22A Br1 2_666 0.95 2.70 3.5577(15) 150 yes
C23 H23A Br2 2_666 0.99 2.89 3.7836(14) 151 yes
C23 H23B Br2 1_656 0.99 2.81 3.7285(17) 154 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 N2 C1 N1 . . . . 0.07(16) ?
C23 N2 C1 N1 . . . . 177.39(12) ?
C7 N1 C1 N2 . . . . -0.09(16) ?
C8 N1 C1 N2 . . . . 179.03(12) ?
C1 N2 C2 C7 . . . . -0.02(15) ?
C23 N2 C2 C7 . . . . -177.35(12) ?
C1 N2 C2 C3 . . . . 177.66(15) ?
C23 N2 C2 C3 . . . . 0.3(2) ?
C7 C2 C3 C4 . . . . 0.0(2) ?
N2 C2 C3 C4 . . . . -177.37(14) ?
C2 C3 C4 C5 . . . . 0.2(2) ?
C3 C4 C5 C6 . . . . -0.3(2) ?
C4 C5 C6 C7 . . . . 0.1(2) ?
C3 C2 C7 C6 . . . . -0.2(2) ?
N2 C2 C7 C6 . . . . 177.79(13) ?
C3 C2 C7 N1 . . . . -177.98(12) ?
N2 C2 C7 N1 . . . . -0.03(15) ?
C5 C6 C7 C2 . . . . 0.1(2) ?
C5 C6 C7 N1 . . . . 177.34(14) ?
C1 N1 C7 C2 . . . . 0.07(15) ?
C8 N1 C7 C2 . . . . -179.04(12) ?
C1 N1 C7 C6 . . . . -177.48(14) ?
C8 N1 C7 C6 . . . . 3.4(2) ?
C1 N1 C8 C9 . . . . -101.05(16) ?
C7 N1 C8 C9 . . . . 77.90(16) ?
N1 C8 C9 C10 . . . . 15.32(18) ?
N1 C8 C9 C14 . . . . -165.31(12) ?
C14 C9 C10 C11 . . . . 0.2(2) ?
C8 C9 C10 C11 . . . . 179.59(13) ?
C9 C10 C11 C12 . . . . -0.3(2) ?
C10 C11 C12 C13 . . . . 0.3(2) ?
C11 C12 C13 C14 . . . . -0.1(2) ?
C12 C13 C14 C9 . . . . -0.1(2) ?
C12 C13 C14 C15 . . . . 176.19(14) ?
C10 C9 C14 C13 . . . . 0.0(2) ?
C8 C9 C14 C13 . . . . -179.39(13) ?
C10 C9 C14 C15 . . . . -176.05(13) ?
C8 C9 C14 C15 . . . . 4.6(2) ?
C22 N3 C15 C14 . . . . 25.2(2) ?
C16 N3 C15 C14 . . . . -161.53(13) ?
C13 C14 C15 N3 . . . . 97.87(16) ?
C9 C14 C15 N3 . . . . -86.02(17) ?
C22 N3 C16 C21 . . . . 0.16(16) ?
C15 N3 C16 C21 . . . . -174.34(13) ?
C22 N3 C16 C17 . . . . -178.32(16) ?
C15 N3 C16 C17 . . . . 7.2(2) ?
C21 C16 C17 C18 . . . . -0.2(2) ?
N3 C16 C17 C18 . . . . 178.08(15) ?
C16 C17 C18 C19 . . . . 0.5(2) ?
C17 C18 C19 C20 . . . . -0.4(3) ?
C18 C19 C20 C21 . . . . 0.0(2) ?
N3 C16 C21 C20 . . . . -178.90(14) ?
C17 C16 C21 C20 . . . . -0.3(2) ?
N3 C16 C21 N4 . . . . 0.06(16) ?
C17 C16 C21 N4 . . . . 178.71(14) ?
C19 C20 C21 C16 . . . . 0.4(2) ?
C19 C20 C21 N4 . . . . -178.30(15) ?
C22 N4 C21 C16 . . . . -0.27(16) ?
C30 N4 C21 C16 . . . . -178.69(13) ?
C22 N4 C21 C20 . . . . 178.56(16) ?
C30 N4 C21 C20 . . . . 0.1(3) ?
C16 N3 C22 N4 . . . . -0.34(17) ?
C15 N3 C22 N4 . . . . 173.71(14) ?
C21 N4 C22 N3 . . . . 0.38(17) ?
C30 N4 C22 N3 . . . . 178.80(13) ?
C1 N2 C23 C24 . . . . 100.16(16) ?
C2 N2 C23 C24 . . . . -82.96(17) ?
N2 C23 C24 C25 . . . . -73.02(16) ?
C23 C24 C25 C26 . . . . -175.79(13) ?
C24 C25 C26 C27 . . . . -67.89(19) ?
C25 C26 C27 C28 . . . . -177.48(16) ?
C26 C27 C28 C29 . . . . -177.98(17) ?
C22 N4 C30 C31 . . . . -113.8(3) ?
C21 N4 C30 C31 . . . . 64.4(3) ?
C22 N4 C30 C31X . . . . -95.1(3) ?
C21 N4 C30 C31X . . . . 83.1(3) ?
N4 C30 C31 C32 . . . . 176.3(6) ?
C31X C30 C31 C32 . . . . 92.5(18) ?
C30 C31 C32 C33 . . . . -147.7(6) ?
C31 C32 C33 C34 . . . . -157.1(7) ?
C32 C33 C34 C35 . . . . -170.0(5) ?
C33 C34 C35 C36 . . . . -170.2(4) ?
N4 C30 C31X C32X . . . . -174.1(4) ?
C31 C30 C31X C32X . . . . -70.8(16) ?
C30 C31X C32X C33X . . . . 154.5(6) ?
C31X C32X C33X C34X . . . . 154.0(6) ?
C32X C33X C34X C35X . . . . 175.9(6) ?
C33X C34X C35X C36X . . . . 179.2(4) ?
