##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
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##############################################################################
                                             
data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2011-02-09
_journal_date_accepted     2011-02-11
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2011
_journal_volume     67
_journal_issue      3
_journal_page_first     o643
_journal_page_last     o643
_journal_paper_category     QO
_journal_coeditor_code     WN2422
_publ_contact_author_name     'Prof. Fun, Hoong-Kun'
_publ_contact_author_address
;
      X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      MALAYSIA
;
_publ_contact_author_email     'hkfun@usm.my'
_publ_contact_author_fax     '604 6579150'
_publ_contact_author_phone     '604 6533652'
_publ_section_title
;\
3,3'-Dibenzyl-1,1'-(2,4,6-trimethyl-m-phenylenedimethylene)\
diimidazol-3-ium dibromide
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Rosenani A. Haque' ?
;
      School of Chemical Sciences
      Universiti Sains Malaysia
      11800 USM, Penang
      Malaysia
;
    'Abbas Washeel Salman' ?
;
      School of Chemical Sciences
      Universiti Sains Malaysia
      11800 USM, Penang
      Malaysia
;
    'Paremala Nadarajan' ?
;
      School of Chemical Sciences
      Universiti Sains Malaysia
      11800 USM, Penang
      Malaysia
;
    'Madhukar Hemamalini' ?
;
      X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      Malaysia
;
    'Hoong-Kun Fun'
;
      Thomson Reuters ResearcherID: A-3561-2009.
;
;
      X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      Malaysia
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
3,3'-Dibenzyl-1,1'-(2,4,6-trimethyl-m-
phenylenedimethylene)diimidazol-3-ium dibromide
;
_chemical_name_common
;
1,3-bis(3-benzylimidazolium-1-ylmethyl)mesitylene dibromide
;
_chemical_formula_moiety     'C31 H34 N4 2+, 2(Br -)'
_chemical_formula_sum     'C31 H34 Br2 N4'
_chemical_formula_iupac     'C31 H34 N4 2+, 2Br -'
_chemical_formula_weight     622.44
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
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'
_cell_length_a     8.9851(2)
_cell_length_b     12.8044(2)
_cell_length_c     25.6419(5)
_cell_angle_alpha     90.00
_cell_angle_beta     102.6110(10)
_cell_angle_gamma     90.00
_cell_volume     2878.90(10)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     9955
_cell_measurement_theta_min     2.32
_cell_measurement_theta_max     29.91
_cell_measurement_temperature     100.00(10)
_exptl_crystal_description     plate
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.49
_exptl_crystal_size_mid     0.43
_exptl_crystal_size_min     0.21
_exptl_crystal_density_diffrn     1.436
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1272
_exptl_absorpt_coefficient_mu     2.842
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2009)'
_exptl_absorpt_correction_T_min     0.3370
_exptl_absorpt_correction_T_max     0.5854
_exptl_special_details
;
The crystal was placed in the cold stream of an Oxford Cryosystems Cobra
open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at
100.0(1) K.
;
_diffrn_ambient_temperature     100.00(10)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type
;
Bruker SMART APEXII CCD area-detector
;
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     .
_diffrn_reflns_number     32884
_diffrn_reflns_av_R_equivalents     0.0358
_diffrn_reflns_av_sigmaI/netI     0.0381
_diffrn_reflns_theta_min     2.28
_diffrn_reflns_theta_max     30.19
_diffrn_reflns_theta_full     30.19
_diffrn_measured_fraction_theta_max     0.994
_diffrn_measured_fraction_theta_full     0.994
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -17
_diffrn_reflns_limit_k_max     18
_diffrn_reflns_limit_l_min     -30
_diffrn_reflns_limit_l_max     36
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     8490
_reflns_number_gt     6550
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0601
_refine_ls_R_factor_gt     0.0404
_refine_ls_wR_factor_gt     0.0938
_refine_ls_wR_factor_ref     0.1009
_refine_ls_goodness_of_fit_ref     1.044
_refine_ls_restrained_S_all     1.044
_refine_ls_number_reflns     8490
_refine_ls_number_parameters     337
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0549P)²+0.6972P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.003
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     1.275
_refine_diff_density_min     -0.403
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'APEX2 (Bruker, 2009)'
_computing_cell_refinement     'SAINT (Bruker, 2009)'
_computing_data_reduction     'SAINT (Bruker, 2009)'
_computing_structure_solution     'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
                             'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
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
    N N1 0.6565(2) 0.78480(15) 0.80723(7) 0.0240(4) Uani d . 1 . .
    N N2 0.4998(2) 0.82215(14) 0.85747(8) 0.0235(4) Uani d . 1 . .
    N N3 0.9596(2) 0.88648(15) 1.09775(8) 0.0244(4) Uani d . 1 . .
    N N4 1.1823(2) 0.82656(14) 1.09554(8) 0.0242(4) Uani d . 1 . .
    C C1 0.9744(3) 0.8645(3) 0.74204(12) 0.0452(7) Uani d . 1 . .
    H H1A 1.0412 0.8088 0.7517 0.054 Uiso calc R 1 . .
    C C2 1.0150(4) 0.9467(3) 0.71276(14) 0.0591(9) Uani d . 1 . .
    H H2A 1.1091 0.9461 0.7033 0.071 Uiso calc R 1 . .
    C C3 0.9160(4) 1.0297(3) 0.69757(12) 0.0504(8) Uani d . 1 . .
    H H3A 0.9425 1.0845 0.6776 0.060 Uiso calc R 1 . .
    C C4 0.7775(3) 1.0297(2) 0.71252(11) 0.0395(6) Uani d . 1 . .
    H H4A 0.7102 1.0850 0.7024 0.047 Uiso calc R 1 . .
    C C5 0.7372(3) 0.94820(19) 0.74249(10) 0.0309(5) Uani d . 1 . .
    H H5A 0.6441 0.9499 0.7527 0.037 Uiso calc R 1 . .
    C C6 0.8349(3) 0.86441(19) 0.75719(9) 0.0274(5) Uani d . 1 . .
    C C7 0.7989(3) 0.77211(19) 0.78865(9) 0.0268(5) Uani d . 1 . .
    H H7A 0.7912 0.7101 0.7665 0.032 Uiso calc R 1 . .
    H H7B 0.8822 0.7616 0.8193 0.032 Uiso calc R 1 . .
    C C8 0.5118(3) 0.76704(19) 0.77738(10) 0.0292(5) Uani d . 1 . .
    H H8A 0.4861 0.7428 0.7424 0.035 Uiso calc R 1 . .
    C C9 0.4139(3) 0.79170(19) 0.80890(10) 0.0298(5) Uani d . 1 . .
    H H9A 0.3080 0.7886 0.7993 0.036 Uiso calc R 1 . .
    C C10 0.6473(2) 0.81899(16) 0.85554(9) 0.0216(4) Uani d . 1 . .
    H H10A 0.7289 0.8374 0.8830 0.026 Uiso calc R 1 . .
    C C11 0.4391(2) 0.85726(18) 0.90348(9) 0.0248(4) Uani d . 1 . .
    H H11A 0.3343 0.8340 0.8989 0.030 Uiso calc R 1 . .
    H H11B 0.4393 0.9330 0.9046 0.030 Uiso calc R 1 . .
    C C12 0.5310(2) 0.81582(16) 0.95579(9) 0.0226(4) Uani d . 1 . .
    C C13 0.6366(2) 0.87950(16) 0.98984(9) 0.0225(4) Uani d . 1 . .
    C C14 0.7047(2) 0.84395(17) 1.04123(9) 0.0236(4) Uani d . 1 . .
    C C15 0.6774(3) 0.74111(18) 1.05665(9) 0.0261(5) Uani d . 1 . .
    C C16 0.5809(3) 0.67784(17) 1.02034(10) 0.0272(5) Uani d . 1 . .
    H H16A 0.5668 0.6090 1.0298 0.033 Uiso calc R 1 . .
    C C17 0.5045(2) 0.71272(17) 0.97056(9) 0.0249(5) Uani d . 1 . .
    C C18 0.7980(3) 0.91657(17) 1.08167(10) 0.0269(5) Uani d . 1 . .
    H H18A 0.7914 0.9865 1.0668 0.032 Uiso calc R 1 . .
    H H18B 0.7547 0.9183 1.1132 0.032 Uiso calc R 1 . .
    C C19 1.0401(2) 0.83681(17) 1.06739(9) 0.0236(4) Uani d . 1 . .
    H H19A 1.0032 0.8134 1.0326 0.028 Uiso calc R 1 . .
    C C20 1.0534(3) 0.90914(19) 1.14621(10) 0.0322(5) Uani d . 1 . .
    H H20A 1.0258 0.9440 1.1745 0.039 Uiso calc R 1 . .
    C C21 1.1933(3) 0.87145(19) 1.14526(10) 0.0315(5) Uani d . 1 . .
    H H21A 1.2800 0.8750 1.1727 0.038 Uiso calc R 1 . .
    C C22 1.3042(3) 0.76808(17) 1.07770(10) 0.0268(5) Uani d . 1 . .
    H H22A 1.4030 0.7916 1.0976 0.032 Uiso calc R 1 . .
    H H22B 1.2985 0.7816 1.0401 0.032 Uiso calc R 1 . .
    C C23 1.2878(2) 0.65205(18) 1.08634(9) 0.0236(4) Uani d . 1 . .
    C C24 1.1996(3) 0.59206(19) 1.04611(10) 0.0307(5) Uani d . 1 . .
    H H24A 1.1554 0.6224 1.0134 0.037 Uiso calc R 1 . .
    C C25 1.1774(3) 0.4869(2) 1.05463(12) 0.0395(6) Uani d . 1 . .
    H H25A 1.1199 0.4464 1.0274 0.047 Uiso calc R 1 . .
    C C26 1.2404(3) 0.44214(19) 1.10336(12) 0.0385(6) Uani d . 1 . .
    H H26A 1.2218 0.3723 1.1095 0.046 Uiso calc R 1 . .
    C C27 1.3312(3) 0.5008(2) 1.14307(11) 0.0360(6) Uani d . 1 . .
    H H27A 1.3760 0.4701 1.1756 0.043 Uiso calc R 1 . .
    C C28 1.3553(3) 0.6056(2) 1.13442(10) 0.0304(5) Uani d . 1 . .
    H H28A 1.4171 0.6450 1.1611 0.036 Uiso calc R 1 . .
    C C29 0.6784(3) 0.98590(17) 0.97157(10) 0.0263(5) Uani d . 1 . .
    H H29A 0.7857 0.9975 0.9843 0.039 Uiso calc R 1 . .
    H H29B 0.6224 1.0388 0.9856 0.039 Uiso calc R 1 . .
    H H29C 0.6535 0.9888 0.9332 0.039 Uiso calc R 1 . .
    C C30 0.3955(3) 0.64136(19) 0.93407(11) 0.0315(5) Uani d . 1 . .
    H H30A 0.3917 0.5752 0.9513 0.047 Uiso calc R 1 . .
    H H30B 0.4297 0.6314 0.9015 0.047 Uiso calc R 1 . .
    H H30C 0.2956 0.6721 0.9262 0.047 Uiso calc R 1 . .
    C C31 0.7495(3) 0.69928(19) 1.11128(10) 0.0336(5) Uani d . 1 . .
    H H31A 0.7026 0.6341 1.1168 0.050 Uiso calc R 1 . .
    H H31B 0.7352 0.7485 1.1380 0.050 Uiso calc R 1 . .
    H H31C 0.8566 0.6887 1.1138 0.050 Uiso calc R 1 . .
    Br Br1 0.03325(2) 0.815324(18) 0.928724(9) 0.02679(7) Uani d . 1 . .
    Br Br2 0.59309(3) 0.572410(19) 0.692096(9) 0.03010(7) Uani d . 1 . .
_geom_special_details
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
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 C10 . 1.333(3) ?
    N1 C8 . 1.376(3) ?
    N1 C7 . 1.468(3) ?
    N2 C10 . 1.337(3) ?
    N2 C9 . 1.371(3) ?
    N2 C11 . 1.474(3) ?
    N3 C19 . 1.334(3) ?
    N3 C20 . 1.371(3) ?
    N3 C18 . 1.472(3) ?
    N4 C19 . 1.330(3) ?
    N4 C21 . 1.382(3) ?
    N4 C22 . 1.479(3) ?
    C1 C2 . 1.387(4) ?
    C1 C6 . 1.391(3) ?
    C1 H1A . 0.9300 ?
    C2 C3 . 1.386(5) ?
    C2 H2A . 0.9300 ?
    C3 C4 . 1.380(4) ?
    C3 H3A . 0.9300 ?
    C4 C5 . 1.390(4) ?
    C4 H4A . 0.9300 ?
    C5 C6 . 1.385(3) ?
    C5 H5A . 0.9300 ?
    C6 C7 . 1.505(3) ?
    C7 H7A . 0.9700 ?
    C7 H7B . 0.9700 ?
    C8 C9 . 1.355(3) ?
    C8 H8A . 0.9300 ?
    C9 H9A . 0.9300 ?
    C10 H10A . 0.9300 ?
    C11 C12 . 1.510(3) ?
    C11 H11A . 0.9700 ?
    C11 H11B . 0.9700 ?
    C12 C13 . 1.402(3) ?
    C12 C17 . 1.408(3) ?
    C13 C14 . 1.402(3) ?
    C13 C29 . 1.515(3) ?
    C14 C15 . 1.412(3) ?
    C14 C18 . 1.504(3) ?
    C15 C16 . 1.387(4) ?
    C15 C31 . 1.507(3) ?
    C16 C17 . 1.385(3) ?
    C16 H16A . 0.9300 ?
    C17 C30 . 1.506(3) ?
    C18 H18A . 0.9700 ?
    C18 H18B . 0.9700 ?
    C19 H19A . 0.9300 ?
    C20 C21 . 1.352(3) ?
    C20 H20A . 0.9300 ?
    C21 H21A . 0.9300 ?
    C22 C23 . 1.514(3) ?
    C22 H22A . 0.9700 ?
    C22 H22B . 0.9700 ?
    C23 C28 . 1.384(3) ?
    C23 C24 . 1.388(3) ?
    C24 C25 . 1.385(3) ?
    C24 H24A . 0.9300 ?
    C25 C26 . 1.379(4) ?
    C25 H25A . 0.9300 ?
    C26 C27 . 1.380(4) ?
    C26 H26A . 0.9300 ?
    C27 C28 . 1.384(4) ?
    C27 H27A . 0.9300 ?
    C28 H28A . 0.9300 ?
    C29 H29A . 0.9600 ?
    C29 H29B . 0.9600 ?
    C29 H29C . 0.9600 ?
    C30 H30A . 0.9600 ?
    C30 H30B . 0.9600 ?
    C30 H30C . 0.9600 ?
    C31 H31A . 0.9600 ?
    C31 H31B . 0.9600 ?
    C31 H31C . 0.9600 ?
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
    C10 N1 C8 . . 109.14(18) ?
    C10 N1 C7 . . 124.97(19) ?
    C8 N1 C7 . . 125.85(19) ?
    C10 N2 C9 . . 108.90(18) ?
    C10 N2 C11 . . 125.60(19) ?
    C9 N2 C11 . . 125.44(19) ?
    C19 N3 C20 . . 109.00(19) ?
    C19 N3 C18 . . 126.1(2) ?
    C20 N3 C18 . . 124.88(19) ?
    C19 N4 C21 . . 109.05(19) ?
    C19 N4 C22 . . 124.8(2) ?
    C21 N4 C22 . . 125.9(2) ?
    C2 C1 C6 . . 120.8(3) ?
    C2 C1 H1A . . 119.6 ?
    C6 C1 H1A . . 119.6 ?
    C3 C2 C1 . . 120.4(3) ?
    C3 C2 H2A . . 119.8 ?
    C1 C2 H2A . . 119.8 ?
    C4 C3 C2 . . 119.0(3) ?
    C4 C3 H3A . . 120.5 ?
    C2 C3 H3A . . 120.5 ?
    C3 C4 C5 . . 120.9(3) ?
    C3 C4 H4A . . 119.6 ?
    C5 C4 H4A . . 119.6 ?
    C6 C5 C4 . . 120.4(2) ?
    C6 C5 H5A . . 119.8 ?
    C4 C5 H5A . . 119.8 ?
    C5 C6 C1 . . 118.7(2) ?
    C5 C6 C7 . . 123.8(2) ?
    C1 C6 C7 . . 117.5(2) ?
    N1 C7 C6 . . 113.04(19) ?
    N1 C7 H7A . . 109.0 ?
    C6 C7 H7A . . 109.0 ?
    N1 C7 H7B . . 109.0 ?
    C6 C7 H7B . . 109.0 ?
    H7A C7 H7B . . 107.8 ?
    C9 C8 N1 . . 106.7(2) ?
    C9 C8 H8A . . 126.6 ?
    N1 C8 H8A . . 126.6 ?
    C8 C9 N2 . . 107.3(2) ?
    C8 C9 H9A . . 126.3 ?
    N2 C9 H9A . . 126.3 ?
    N1 C10 N2 . . 107.92(19) ?
    N1 C10 H10A . . 126.0 ?
    N2 C10 H10A . . 126.0 ?
    N2 C11 C12 . . 112.17(17) ?
    N2 C11 H11A . . 109.2 ?
    C12 C11 H11A . . 109.2 ?
    N2 C11 H11B . . 109.2 ?
    C12 C11 H11B . . 109.2 ?
    H11A C11 H11B . . 107.9 ?
    C13 C12 C17 . . 120.6(2) ?
    C13 C12 C11 . . 120.90(19) ?
    C17 C12 C11 . . 118.5(2) ?
    C12 C13 C14 . . 119.6(2) ?
    C12 C13 C29 . . 120.7(2) ?
    C14 C13 C29 . . 119.7(2) ?
    C13 C14 C15 . . 119.9(2) ?
    C13 C14 C18 . . 120.7(2) ?
    C15 C14 C18 . . 119.2(2) ?
    C16 C15 C14 . . 118.6(2) ?
    C16 C15 C31 . . 119.7(2) ?
    C14 C15 C31 . . 121.7(2) ?
    C17 C16 C15 . . 122.8(2) ?
    C17 C16 H16A . . 118.6 ?
    C15 C16 H16A . . 118.6 ?
    C16 C17 C12 . . 118.1(2) ?
    C16 C17 C30 . . 120.1(2) ?
    C12 C17 C30 . . 121.8(2) ?
    N3 C18 C14 . . 113.49(18) ?
    N3 C18 H18A . . 108.9 ?
    C14 C18 H18A . . 108.9 ?
    N3 C18 H18B . . 108.9 ?
    C14 C18 H18B . . 108.9 ?
    H18A C18 H18B . . 107.7 ?
    N4 C19 N3 . . 108.0(2) ?
    N4 C19 H19A . . 126.0 ?
    N3 C19 H19A . . 126.0 ?
    C21 C20 N3 . . 107.3(2) ?
    C21 C20 H20A . . 126.3 ?
    N3 C20 H20A . . 126.3 ?
    C20 C21 N4 . . 106.6(2) ?
    C20 C21 H21A . . 126.7 ?
    N4 C21 H21A . . 126.7 ?
    N4 C22 C23 . . 110.43(17) ?
    N4 C22 H22A . . 109.6 ?
    C23 C22 H22A . . 109.6 ?
    N4 C22 H22B . . 109.6 ?
    C23 C22 H22B . . 109.6 ?
    H22A C22 H22B . . 108.1 ?
    C28 C23 C24 . . 119.5(2) ?
    C28 C23 C22 . . 121.0(2) ?
    C24 C23 C22 . . 119.5(2) ?
    C25 C24 C23 . . 119.9(2) ?
    C25 C24 H24A . . 120.0 ?
    C23 C24 H24A . . 120.0 ?
    C26 C25 C24 . . 120.2(3) ?
    C26 C25 H25A . . 119.9 ?
    C24 C25 H25A . . 119.9 ?
    C25 C26 C27 . . 120.1(2) ?
    C25 C26 H26A . . 119.9 ?
    C27 C26 H26A . . 119.9 ?
    C26 C27 C28 . . 119.8(2) ?
    C26 C27 H27A . . 120.1 ?
    C28 C27 H27A . . 120.1 ?
    C23 C28 C27 . . 120.4(2) ?
    C23 C28 H28A . . 119.8 ?
    C27 C28 H28A . . 119.8 ?
    C13 C29 H29A . . 109.5 ?
    C13 C29 H29B . . 109.5 ?
    H29A C29 H29B . . 109.5 ?
    C13 C29 H29C . . 109.5 ?
    H29A C29 H29C . . 109.5 ?
    H29B C29 H29C . . 109.5 ?
    C17 C30 H30A . . 109.5 ?
    C17 C30 H30B . . 109.5 ?
    H30A C30 H30B . . 109.5 ?
    C17 C30 H30C . . 109.5 ?
    H30A C30 H30C . . 109.5 ?
    H30B C30 H30C . . 109.5 ?
    C15 C31 H31A . . 109.5 ?
    C15 C31 H31B . . 109.5 ?
    H31A C31 H31B . . 109.5 ?
    C15 C31 H31C . . 109.5 ?
    H31A C31 H31C . . 109.5 ?
    H31B C31 H31C . . 109.5 ?
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
    C6 C1 C2 C3 . . . . -0.7(5) ?
    C1 C2 C3 C4 . . . . 0.7(5) ?
    C2 C3 C4 C5 . . . . 0.2(4) ?
    C3 C4 C5 C6 . . . . -1.0(4) ?
    C4 C5 C6 C1 . . . . 0.9(4) ?
    C4 C5 C6 C7 . . . . -178.8(2) ?
    C2 C1 C6 C5 . . . . -0.1(4) ?
    C2 C1 C6 C7 . . . . 179.7(3) ?
    C10 N1 C7 C6 . . . . -96.1(3) ?
    C8 N1 C7 C6 . . . . 81.5(3) ?
    C5 C6 C7 N1 . . . . -6.2(3) ?
    C1 C6 C7 N1 . . . . 174.1(2) ?
    C10 N1 C8 C9 . . . . 0.2(3) ?
    C7 N1 C8 C9 . . . . -177.8(2) ?
    N1 C8 C9 N2 . . . . -1.0(3) ?
    C10 N2 C9 C8 . . . . 1.6(3) ?
    C11 N2 C9 C8 . . . . 179.0(2) ?
    C8 N1 C10 N2 . . . . 0.8(2) ?
    C7 N1 C10 N2 . . . . 178.76(19) ?
    C9 N2 C10 N1 . . . . -1.5(2) ?
    C11 N2 C10 N1 . . . . -178.90(19) ?
    C10 N2 C11 C12 . . . . -42.9(3) ?
    C9 N2 C11 C12 . . . . 140.1(2) ?
    N2 C11 C12 C13 . . . . 101.9(2) ?
    N2 C11 C12 C17 . . . . -80.3(2) ?
    C17 C12 C13 C14 . . . . -6.5(3) ?
    C11 C12 C13 C14 . . . . 171.21(18) ?
    C17 C12 C13 C29 . . . . 173.11(18) ?
    C11 C12 C13 C29 . . . . -9.2(3) ?
    C12 C13 C14 C15 . . . . 5.7(3) ?
    C29 C13 C14 C15 . . . . -173.94(18) ?
    C12 C13 C14 C18 . . . . -169.92(18) ?
    C29 C13 C14 C18 . . . . 10.4(3) ?
    C13 C14 C15 C16 . . . . -1.0(3) ?
    C18 C14 C15 C16 . . . . 174.71(19) ?
    C13 C14 C15 C31 . . . . 179.4(2) ?
    C18 C14 C15 C31 . . . . -5.0(3) ?
    C14 C15 C16 C17 . . . . -3.1(3) ?
    C31 C15 C16 C17 . . . . 176.5(2) ?
    C15 C16 C17 C12 . . . . 2.4(3) ?
    C15 C16 C17 C30 . . . . -177.1(2) ?
    C13 C12 C17 C16 . . . . 2.5(3) ?
    C11 C12 C17 C16 . . . . -175.25(18) ?
    C13 C12 C17 C30 . . . . -178.02(19) ?
    C11 C12 C17 C30 . . . . 4.2(3) ?
    C19 N3 C18 C14 . . . . 30.3(3) ?
    C20 N3 C18 C14 . . . . -152.4(2) ?
    C13 C14 C18 N3 . . . . -116.1(2) ?
    C15 C14 C18 N3 . . . . 68.3(3) ?
    C21 N4 C19 N3 . . . . -0.3(3) ?
    C22 N4 C19 N3 . . . . 174.75(19) ?
    C20 N3 C19 N4 . . . . 0.5(3) ?
    C18 N3 C19 N4 . . . . 178.19(19) ?
    C19 N3 C20 C21 . . . . -0.6(3) ?
    C18 N3 C20 C21 . . . . -178.2(2) ?
    N3 C20 C21 N4 . . . . 0.4(3) ?
    C19 N4 C21 C20 . . . . 0.0(3) ?
    C22 N4 C21 C20 . . . . -175.0(2) ?
    C19 N4 C22 C23 . . . . -79.9(3) ?
    C21 N4 C22 C23 . . . . 94.4(3) ?
    N4 C22 C23 C28 . . . . -88.0(3) ?
    N4 C22 C23 C24 . . . . 89.8(3) ?
    C28 C23 C24 C25 . . . . 1.2(3) ?
    C22 C23 C24 C25 . . . . -176.7(2) ?
    C23 C24 C25 C26 . . . . 1.2(4) ?
    C24 C25 C26 C27 . . . . -2.7(4) ?
    C25 C26 C27 C28 . . . . 1.8(4) ?
    C24 C23 C28 C27 . . . . -2.1(3) ?
    C22 C23 C28 C27 . . . . 175.7(2) ?
    C26 C27 C28 C23 . . . . 0.6(4) ?
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
    C7 H7A Br2 . 0.97 2.90 3.754(2) 147 yes
    C7 H7B Br1 1_655 0.97 2.92 3.787(2) 149 yes
    C8 H8A Br2 . 0.93 2.81 3.496(3) 132 yes
    C10 H10A Br1 1_655 0.93 2.74 3.565(2) 148 yes
    C18 H18B Br2 4_576 0.97 2.74 3.702(2) 172 yes
    C19 H19A Br1 1_655 0.93 2.74 3.553(2) 147 yes
    C21 H21A Br2 4_676 0.93 2.83 3.603(3) 141 yes
