##############################################################################
###                                                                        ###
###        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.                                        #
#                                                                            #
##############################################################################
                                             
data_global
_audit_creation_method     'PLATON <TABLE ACC> option'
_journal_date_recd_electronic     2008-09-15
_journal_date_accepted     2008-09-25
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue     11
_journal_page_first     o2136
_journal_page_last     o2137
_journal_paper_category     QO
_journal_coeditor_code     SJ2540
_publ_contact_author_name
; Dr Mehmet Akkurt
;
_publ_contact_author_address
; Department of Physics
  Faculty of Arts and Sciences
  Erciyes University
  38039 Kayseri
  Turkey
;
_publ_contact_author_email     akkurt@erciyes.edu.tr
_publ_contact_author_fax     '+90-352-4374933'
_publ_contact_author_phone     '+90-352-4374901 ext. 33106'
_publ_section_title
;\
(E)-1,1'-Bis[(E)-but-2-enyl]-3,3'-(propane-1,3-diyl)\
bis(1H-benzimidazol-3-ium) dibromide monohydrate
;
loop_
    _publ_author_name
    _publ_author_address
    'Mehmet Akkurt'
;
  Department of Physics
  Faculty of Arts and Sciences
  Erciyes University
  38039 Kayseri
  Turkey
;
    'Sema Öztürk Yıldırım'
;
  Department of Physics
  Faculty of Arts and Sciences
  Erciyes University
  38039 Kayseri
  Turkey
;
    'Nihat Şireci'
;
  Department of Chemistry,
  Faculty of Arts and Sciences,
  Adıyaman University,
  Adıyaman,
  Turkey
;
    'Hasan Küçükbay'
;
  Department of Chemistry
  Faculty of Arts and Sciences
  Ínönü University
  44280 Malatya
  Turkey
;
    'Orhan Büyükgüngör'
;
   Department of Physics
   Faculty of Arts and Sciences
   Ondokuz Mayıs University
   55139 Samsun
   Turkey
;
data_I
_chemical_name_systematic
;
(E)-1,1'-Bis[(E)-but-2-enyl]-3,3'-(propane-1,3-\
diyl)bis(1H-benzimidazol-3-ium) dibromide monohydrate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C25 H30 N4 2+, 2(Br -), H2 O'
_chemical_formula_sum     'C25 H32 Br2 N4 O'
_chemical_formula_structural     ?
_chemical_formula_iupac     'C25 H30 N4 2+, 2Br -, H2 O'
_chemical_formula_weight     564.35
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_site_id
    _symmetry_equiv_pos_as_xyz
    1 x,y,z
    2 -x,-y,-z
_cell_length_a     8.7989(9)
_cell_length_b     11.1878(13)
_cell_length_c     14.8813(14)
_cell_angle_alpha     106.381(8)
_cell_angle_beta     96.490(8)
_cell_angle_gamma     106.227(8)
_cell_volume     1319.9(3)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     25470
_cell_measurement_theta_min     2.01
_cell_measurement_theta_max     28.01
_cell_measurement_temperature     296
_cell_special_details
;
;
_exptl_crystal_description     'prismatic plate'
_exptl_crystal_colour     'light yellow'
_exptl_crystal_size_max     0.530
_exptl_crystal_size_mid     0.453
_exptl_crystal_size_min     0.310
_exptl_crystal_size_rad     ?
_exptl_crystal_density_diffrn     1.420
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'Not Measured'
_exptl_crystal_F_000     576
loop_
    _exptl_crystal_face_index_h
    _exptl_crystal_face_index_k
    _exptl_crystal_face_index_l
    _exptl_crystal_face_perp_dist
    3 -4 -22 0.1650
    0 0 1 0.1330
    -6 -29 26 0.2590
    5 29 -26 0.2920
    7 27 -22 0.2810
    7 21 -8 0.2940
    -4 3 1 0.2550
    -17 13 -24 0.3429
    3 -18 22 0.2450
    -1 -8 3 0.2666
    -6 1 11 0.2440
    -6 -1 0 0.3485
    4 -3 -1 0.3468
_exptl_absorpt_coefficient_mu     3.094
_exptl_absorpt_correction_type     'integration'
_exptl_absorpt_process_details     '(X-RED32; Stoe & Cie, 2002)'
_exptl_absorpt_correction_T_min     0.291
_exptl_absorpt_correction_T_max     0.447
_exptl_special_details
;
;
_diffrn_ambient_temperature     296
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     'plane graphite'
_diffrn_measurement_device_type     'Stoe IPDSII'
_diffrn_measurement_device     '2-circle goniometer'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     6.67
_diffrn_reflns_number     16109
_diffrn_reflns_av_R_equivalents     0.0627
_diffrn_reflns_av_sigmaI/netI     0.0618
_diffrn_reflns_theta_min     2.46
_diffrn_reflns_theta_max     27.72
_diffrn_reflns_theta_full     27.72
_diffrn_measured_fraction_theta_max     0.993
_diffrn_measured_fraction_theta_full     0.993
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -14
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     19
_diffrn_reflns_reduction_process
;
;
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement on F² for ALL reflections except those flagged by the user
for potential systematic errors. Weighted R-factors wR and all
goodnesses of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The observed criterion of F² > σ(F²)
is used only for calculating -R-factor-obs 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     6181
_reflns_number_gt     4101
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0904
_refine_ls_R_factor_gt     0.0538
_refine_ls_wR_factor_gt     0.1081
_refine_ls_wR_factor_ref     0.1239
_refine_ls_goodness_of_fit_ref     1.047
_refine_ls_restrained_S_all     1.047
_refine_ls_number_reflns     6181
_refine_ls_number_parameters     297
_refine_ls_number_restraints     0
_refine_ls_number_constraints     ?
_refine_ls_hydrogen_treatment     'mixed'
_refine_ls_weighting_scheme     'calc'
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0416P)²+0.9807P] 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     ?
_refine_ls_shift/su_max_lt     0.001
_refine_ls_shift/su_mean     <0.001
_refine_diff_density_max     0.565
_refine_diff_density_min     -0.406
_refine_ls_extinction_method     'none'
_refine_ls_abs_structure_details     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    O O 0.0106 0.0060 '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'
    H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'X-AREA (Stoe & Cie, 2002)'
_computing_cell_refinement     'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction     'X-RED32 (Stoe & Cie, 2002)'
_computing_structure_solution     'SIR97 (Altomare et al.,  1999)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material     'WINGX (Farrugia, 1999)'
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_thermal_displace_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    N N1 0.7390(4) 0.6064(4) 0.4072(2) 0.0525(10) Uani . . 1.000
    N N2 0.4931(4) 0.5116(3) 0.3227(2) 0.0495(10) Uani . . 1.000
    N N3 0.1559(4) 0.3113(3) 0.0400(2) 0.0463(10) Uani . . 1.000
    N N4 0.2504(4) 0.1820(4) -0.0600(2) 0.0557(11) Uani . . 1.000
    C C1 1.1336(19) 0.851(2) 0.3031(16) 0.400(19) Uani . . 1.000
    C C2 1.0601(14) 0.774(2) 0.3445(13) 0.292(12) Uani . . 1.000
    C C3 0.9949(10) 0.7489(12) 0.4033(10) 0.177(6) Uani . . 1.000
    C C4 0.9166(5) 0.6413(6) 0.4322(3) 0.0707(18) Uani . . 1.000
    C C5 0.6392(5) 0.6485(4) 0.4651(3) 0.0485(12) Uani . . 1.000
    C C6 0.6724(5) 0.7321(4) 0.5592(3) 0.0572(14) Uani . . 1.000
    C C7 0.5407(6) 0.7523(5) 0.5946(3) 0.0661(16) Uani . . 1.000
    C C8 0.3830(6) 0.6909(5) 0.5413(3) 0.0673(17) Uani . . 1.000
    C C9 0.3504(5) 0.6076(4) 0.4486(3) 0.0559(14) Uani . . 1.000
    C C10 0.4821(5) 0.5886(4) 0.4116(2) 0.0451(11) Uani . . 1.000
    C C11 0.6481(5) 0.5246(4) 0.3234(3) 0.0546(14) Uani . . 1.000
    C C12 0.3576(5) 0.4279(4) 0.2430(3) 0.0524(12) Uani . . 1.000
    C C13 0.3047(5) 0.5057(4) 0.1841(3) 0.0536(12) Uani . . 1.000
    C C14 0.1475(5) 0.4283(4) 0.1120(3) 0.0547(14) Uani . . 1.000
    C C15 0.0246(5) 0.2004(4) -0.0130(2) 0.0462(11) Uani . . 1.000
    C C16 -0.1379(5) 0.1681(5) -0.0101(3) 0.0607(16) Uani . . 1.000
    C C17 -0.2356(6) 0.0474(5) -0.0719(4) 0.0730(17) Uani . . 1.000
    C C18 -0.1753(7) -0.0361(5) -0.1343(4) 0.0756(17) Uani . . 1.000
    C C19 -0.0147(6) -0.0054(5) -0.1380(3) 0.0692(18) Uani . . 1.000
    C C20 0.0849(5) 0.1169(4) -0.0768(3) 0.0528(14) Uani . . 1.000
    C C21 0.2866(5) 0.2959(4) 0.0079(3) 0.0520(14) Uani . . 1.000
    C C22 0.3684(7) 0.1338(7) -0.1103(3) 0.084(2) Uani . . 1.000
    C C23 0.3596(8) 0.1486(7) -0.2051(4) 0.094(3) Uani . . 1.000
    C C24 0.3622(10) 0.0582(8) -0.2808(5) 0.116(3) Uani . . 1.000
    C C25 0.3606(14) 0.0664(10) -0.3775(6) 0.162(5) Uani . . 1.000
    O O1 0.5845(5) 0.2069(5) 0.1612(4) 0.0878(16) Uani . . 1.000
    Br Br1 0.70894(5) 0.46584(5) 0.08608(3) 0.0654(2) Uani . . 1.000
    Br Br2 -0.05435(5) 0.30445(5) 0.30568(3) 0.0648(2) Uani . . 1.000
    H H1A 1.16160 0.80090 0.24750 0.5960 Uiso calc R 1.000
    H H1B 1.23030 0.91410 0.34640 0.5960 Uiso calc R 1.000
    H H1C 1.06430 0.89630 0.28420 0.5960 Uiso calc R 1.000
    H H2 1.05770 0.69140 0.30580 0.3530 Uiso calc R 1.000
    H H3 0.99330 0.82660 0.44670 0.2120 Uiso calc R 1.000
    H H4A 0.95090 0.66410 0.50090 0.0840 Uiso calc R 1.000
    H H4B 0.94770 0.56570 0.40120 0.0840 Uiso calc R 1.000
    H H6 0.77720 0.77180 0.59580 0.0680 Uiso calc R 1.000
    H H7 0.55760 0.80940 0.65670 0.0800 Uiso calc R 1.000
    H H8 0.29780 0.70650 0.56900 0.0810 Uiso calc R 1.000
    H H9 0.24520 0.56620 0.41270 0.0670 Uiso calc R 1.000
    H H11 0.68710 0.48220 0.27240 0.0660 Uiso calc R 1.000
    H H12A 0.26710 0.38660 0.26790 0.0630 Uiso calc R 1.000
    H H12B 0.38910 0.35850 0.20210 0.0630 Uiso calc R 1.000
    H H13A 0.29250 0.58410 0.22700 0.0650 Uiso calc R 1.000
    H H13B 0.38890 0.53390 0.15050 0.0650 Uiso calc R 1.000
    H H14A 0.06290 0.40110 0.14570 0.0660 Uiso calc R 1.000
    H H14B 0.11790 0.48530 0.07980 0.0660 Uiso calc R 1.000
    H H16 -0.17850 0.22470 0.03130 0.0730 Uiso calc R 1.000
    H H17 -0.34570 0.02090 -0.07200 0.0870 Uiso calc R 1.000
    H H18 -0.24680 -0.11630 -0.17550 0.0910 Uiso calc R 1.000
    H H19 0.02510 -0.06320 -0.17900 0.0830 Uiso calc R 1.000
    H H21 0.38980 0.35770 0.03050 0.0620 Uiso calc R 1.000
    H H22A 0.47680 0.18260 -0.07220 0.1010 Uiso calc R 1.000
    H H22B 0.34740 0.04150 -0.11690 0.1010 Uiso calc R 1.000
    H H23 0.35180 0.22730 -0.21120 0.1130 Uiso calc R 1.000
    H H24 0.36530 -0.02080 -0.27320 0.1390 Uiso calc R 1.000
    H H25A 0.36370 -0.01500 -0.41980 0.2430 Uiso calc R 1.000
    H H25B 0.45340 0.13740 -0.37610 0.2430 Uiso calc R 1.000
    H H25C 0.26380 0.08230 -0.39980 0.2430 Uiso calc R 1.000
    H HW1 0.625(9) 0.268(7) 0.143(5) 0.11(3) Uiso . . 1.000
    H HW2 0.677(10) 0.224(7) 0.201(5) 0.12(3) Uiso . . 1.000
_geom_special_details
;
Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O1 HW2 . . 0.89(9) no
    O1 HW1 . . 0.81(8) no
    N1 C11 . . 1.324(5) no
    N1 C4 . . 1.476(6) no
    N1 C5 . . 1.382(6) no
    N2 C11 . . 1.329(6) no
    N2 C12 . . 1.461(5) no
    N2 C10 . . 1.391(4) no
    N3 C21 . . 1.330(6) no
    N3 C14 . . 1.466(5) no
    N3 C15 . . 1.392(5) no
    N4 C22 . . 1.480(7) no
    N4 C20 . . 1.391(6) no
    N4 C21 . . 1.312(6) no
    C1 C2 . . 1.27(3) no
    C2 C3 . . 1.16(2) no
    C3 C4 . . 1.416(15) no
    C5 C6 . . 1.392(6) no
    C5 C10 . . 1.388(6) no
    C6 C7 . . 1.374(7) no
    C7 C8 . . 1.392(7) no
    C8 C9 . . 1.375(6) no
    C9 C10 . . 1.381(6) no
    C12 C13 . . 1.519(6) no
    C13 C14 . . 1.512(6) no
    C15 C16 . . 1.382(7) no
    C15 C20 . . 1.395(6) no
    C16 C17 . . 1.371(8) no
    C17 C18 . . 1.384(8) no
    C18 C19 . . 1.369(8) no
    C19 C20 . . 1.384(7) no
    C22 C23 . . 1.462(8) no
    C23 C24 . . 1.292(10) no
    C24 C25 . . 1.466(12) no
    C1 H1C . . 0.9600 no
    C1 H1A . . 0.9600 no
    C1 H1B . . 0.9600 no
    C2 H2 . . 0.9300 no
    C3 H3 . . 0.9300 no
    C4 H4A . . 0.9700 no
    C4 H4B . . 0.9700 no
    C6 H6 . . 0.9300 no
    C7 H7 . . 0.9300 no
    C8 H8 . . 0.9300 no
    C9 H9 . . 0.9300 no
    C11 H11 . . 0.9300 no
    C12 H12A . . 0.9700 no
    C12 H12B . . 0.9700 no
    C13 H13A . . 0.9700 no
    C13 H13B . . 0.9700 no
    C14 H14A . . 0.9700 no
    C14 H14B . . 0.9700 no
    C16 H16 . . 0.9300 no
    C17 H17 . . 0.9300 no
    C18 H18 . . 0.9300 no
    C19 H19 . . 0.9300 no
    C21 H21 . . 0.9300 no
    C22 H22B . . 0.9700 no
    C22 H22A . . 0.9700 no
    C23 H23 . . 0.9300 no
    C24 H24 . . 0.9300 no
    C25 H25C . . 0.9600 no
    C25 H25A . . 0.9600 no
    C25 H25B . . 0.9600 no
loop_
    _geom_contact_atom_site_label_1
    _geom_contact_atom_site_label_2
    _geom_contact_distance
    _geom_contact_site_symmetry_1
    _geom_contact_site_symmetry_2
    _geom_contact_publ_flag
    Br1 C21 3.550(5) . . no
    Br1 O1 3.342(6) . . no
    Br1 C11 3.536(4) . . no
    Br1 C14 3.696(4) . 2_665 no
    Br1 C21 3.335(5) . 2_665 no
    Br1 N3 3.555(3) . 2_665 no
    Br2 O1 3.333(5) . 1_455 no
    Br1 HW1 2.54(8) . . no
    Br1 H11 2.7600 . . no
    Br1 H21 2.6500 . . no
    Br1 H16 3.0600 . 1_655 no
    Br1 H14B 3.1400 . 2_665 no
    Br1 H21 3.2000 . 2_665 no
    Br2 H14A 3.0500 . . no
    Br2 HW2 2.45(8) . 1_455 no
    Br2 H4B 2.8600 . 1_455 no
    Br2 H4A 2.8100 . 2_666 no
    Br2 H6 3.1400 . 2_666 no
    Br2 H8 2.9900 . 2_566 no
    Br2 H19 2.9200 . 2_555 no
    Br2 H9 3.1900 . . no
    Br2 H12A 2.8900 . . no
    O1 Br2 3.333(5) . 1_655 no
    O1 C17 3.369(8) . 2_555 no
    O1 Br1 3.342(6) . . no
    O1 H12B 2.7400 . . no
    O1 H22B 2.9200 . 2_655 no
    O1 H11 2.8800 . . no
    O1 H18 2.9100 . 2_555 no
    O1 H17 2.6700 . 2_555 no
    N1 N2 2.177(5) . . no
    N2 N1 2.177(5) . . no
    N3 Br1 3.555(3) . 2_665 no
    N3 N4 2.176(5) . . no
    N4 N3 2.176(5) . . no
    N3 H12B 2.8000 . . no
    C1 C19 3.60(2) . 2_665 no
    C5 C9 3.473(6) . 2_666 no
    C8 C11 3.526(7) . 2_666 no
    C9 C5 3.473(6) . 2_666 no
    C11 C8 3.526(7) . 2_666 no
    C11 Br1 3.536(4) . . no
    C12 C21 3.300(6) . . no
    C14 Br1 3.696(4) . 2_665 no
    C15 C18 3.594(7) . 2_555 no
    C15 C19 3.538(6) . 2_555 no
    C16 C19 3.596(7) . 2_555 no
    C17 O1 3.369(8) . 2_555 no
    C18 C20 3.572(7) . 2_555 no
    C18 C15 3.594(7) . 2_555 no
    C19 C16 3.596(7) . 2_555 no
    C19 C15 3.538(6) . 2_555 no
    C19 C1 3.60(2) . 2_665 no
    C20 C18 3.572(7) . 2_555 no
    C21 Br1 3.550(5) . . no
    C21 C12 3.300(6) . . no
    C21 Br1 3.335(5) . 2_665 no
    C4 H6 3.0400 . . no
    C6 H4A 2.9100 . . no
    C9 H12A 2.9400 . . no
    C10 H13A 3.0300 . . no
    C12 H9 2.9900 . . no
    C13 H21 2.7300 . . no
    C14 H16 2.9800 . . no
    C16 H14A 2.9000 . . no
    C19 H22B 3.0400 . . no
    C19 H1C 2.8300 . 2_665 no
    C21 H12B 2.7500 . . no
    C21 H13B 2.7300 . . no
    C22 H19 3.0600 . . no
    HW1 H11 2.4900 . . no
    HW1 Br1 2.54(8) . . no
    HW1 H16 2.5800 . 1_655 no
    H1C C19 2.8300 . 2_665 no
    H2 H4B 2.3700 . . no
    HW2 Br2 2.45(8) . 1_655 no
    H4A H6 2.5200 . . no
    H4A C6 2.9100 . . no
    H4A Br2 2.8100 . 2_666 no
    H4B H2 2.3700 . . no
    H4B H11 2.5700 . . no
    H4B Br2 2.8600 . 1_655 no
    H6 Br2 3.1400 . 2_666 no
    H6 C4 3.0400 . . no
    H6 H4A 2.5200 . . no
    H8 Br2 2.9900 . 2_566 no
    H9 H12A 2.5700 . . no
    H9 C12 2.9900 . . no
    H9 Br2 3.1900 . . no
    H11 Br1 2.7600 . . no
    H11 H4B 2.5700 . . no
    H11 O1 2.8800 . . no
    H11 HW1 2.4900 . . no
    H11 H12B 2.5300 . . no
    H12A C9 2.9400 . . no
    H12A H9 2.5700 . . no
    H12A Br2 2.8900 . . no
    H12A H14A 2.4800 . . no
    H12B N3 2.8000 . . no
    H12B O1 2.7400 . . no
    H12B H18 2.5400 . 2_555 no
    H12B H21 2.5500 . . no
    H12B H11 2.5300 . . no
    H12B C21 2.7500 . . no
    H13A C10 3.0300 . . no
    H13B H21 2.2600 . . no
    H13B C21 2.7300 . . no
    H14A Br2 3.0500 . . no
    H14A C16 2.9000 . . no
    H14A H12A 2.4800 . . no
    H14A H16 2.5000 . . no
    H14B Br1 3.1400 . 2_665 no
    H16 C14 2.9800 . . no
    H16 Br1 3.0600 . 1_455 no
    H16 HW1 2.5800 . 1_455 no
    H16 H14A 2.5000 . . no
    H17 O1 2.6700 . 2_555 no
    H18 H12B 2.5400 . 2_555 no
    H18 O1 2.9100 . 2_555 no
    H19 C22 3.0600 . . no
    H19 Br2 2.9200 . 2_555 no
    H21 Br1 2.6500 . . no
    H21 C13 2.7300 . . no
    H21 H12B 2.5500 . . no
    H21 H13B 2.2600 . . no
    H21 H22A 2.4800 . . no
    H21 Br1 3.2000 . 2_665 no
    H22A H21 2.4800 . . no
    H22B C19 3.0400 . . no
    H22B H24 2.2700 . . no
    H22B O1 2.9200 . 2_655 no
    H24 H22B 2.2700 . . no
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_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    HW1 O1 HW2 . . . 91(7) no
    C4 N1 C11 . . . 124.1(4) no
    C5 N1 C11 . . . 108.5(4) no
    C4 N1 C5 . . . 127.4(3) no
    C10 N2 C11 . . . 108.2(3) no
    C11 N2 C12 . . . 125.7(3) no
    C10 N2 C12 . . . 126.1(4) no
    C14 N3 C15 . . . 125.6(4) no
    C15 N3 C21 . . . 107.6(3) no
    C14 N3 C21 . . . 126.6(4) no
    C20 N4 C21 . . . 108.8(4) no
    C20 N4 C22 . . . 126.5(4) no
    C21 N4 C22 . . . 124.7(4) no
    C1 C2 C3 . . . 155(2) no
    C2 C3 C4 . . . 142.0(16) no
    N1 C4 C3 . . . 111.2(6) no
    N1 C5 C10 . . . 106.8(3) no
    C6 C5 C10 . . . 121.5(4) no
    N1 C5 C6 . . . 131.7(4) no
    C5 C6 C7 . . . 115.8(4) no
    C6 C7 C8 . . . 122.6(4) no
    C7 C8 C9 . . . 121.4(5) no
    C8 C9 C10 . . . 116.4(4) no
    N2 C10 C5 . . . 106.3(4) no
    C5 C10 C9 . . . 122.1(3) no
    N2 C10 C9 . . . 131.6(4) no
    N1 C11 N2 . . . 110.2(4) no
    N2 C12 C13 . . . 111.9(4) no
    C12 C13 C14 . . . 113.4(4) no
    N3 C14 C13 . . . 113.3(4) no
    N3 C15 C16 . . . 131.2(4) no
    C16 C15 C20 . . . 122.0(4) no
    N3 C15 C20 . . . 106.8(4) no
    C15 C16 C17 . . . 116.0(4) no
    C16 C17 C18 . . . 121.9(5) no
    C17 C18 C19 . . . 122.7(5) no
    C18 C19 C20 . . . 115.9(5) no
    N4 C20 C15 . . . 105.8(4) no
    N4 C20 C19 . . . 132.7(4) no
    C15 C20 C19 . . . 121.4(4) no
    N3 C21 N4 . . . 110.9(4) no
    N4 C22 C23 . . . 111.9(5) no
    C22 C23 C24 . . . 123.5(7) no
    C23 C24 C25 . . . 127.2(9) no
    C2 C1 H1A . . . 110.00 no
    C2 C1 H1B . . . 109.00 no
    H1A C1 H1B . . . 109.00 no
    H1A C1 H1C . . . 109.00 no
    H1B C1 H1C . . . 109.00 no
    C2 C1 H1C . . . 109.00 no
    C3 C2 H2 . . . 103.00 no
    C1 C2 H2 . . . 103.00 no
    C2 C3 H3 . . . 109.00 no
    C4 C3 H3 . . . 109.00 no
    N1 C4 H4A . . . 109.00 no
    N1 C4 H4B . . . 109.00 no
    C3 C4 H4B . . . 109.00 no
    H4A C4 H4B . . . 108.00 no
    C3 C4 H4A . . . 109.00 no
    C5 C6 H6 . . . 122.00 no
    C7 C6 H6 . . . 122.00 no
    C6 C7 H7 . . . 119.00 no
    C8 C7 H7 . . . 119.00 no
    C9 C8 H8 . . . 119.00 no
    C7 C8 H8 . . . 119.00 no
    C10 C9 H9 . . . 122.00 no
    C8 C9 H9 . . . 122.00 no
    N1 C11 H11 . . . 125.00 no
    N2 C11 H11 . . . 125.00 no
    N2 C12 H12A . . . 109.00 no
    N2 C12 H12B . . . 109.00 no
    C13 C12 H12B . . . 109.00 no
    H12A C12 H12B . . . 108.00 no
    C13 C12 H12A . . . 109.00 no
    C12 C13 H13A . . . 109.00 no
    C14 C13 H13A . . . 109.00 no
    C14 C13 H13B . . . 109.00 no
    C12 C13 H13B . . . 109.00 no
    H13A C13 H13B . . . 108.00 no
    N3 C14 H14B . . . 109.00 no
    C13 C14 H14A . . . 109.00 no
    C13 C14 H14B . . . 109.00 no
    H14A C14 H14B . . . 108.00 no
    N3 C14 H14A . . . 109.00 no
    C17 C16 H16 . . . 122.00 no
    C15 C16 H16 . . . 122.00 no
    C16 C17 H17 . . . 119.00 no
    C18 C17 H17 . . . 119.00 no
    C19 C18 H18 . . . 119.00 no
    C17 C18 H18 . . . 119.00 no
    C18 C19 H19 . . . 122.00 no
    C20 C19 H19 . . . 122.00 no
    N3 C21 H21 . . . 125.00 no
    N4 C21 H21 . . . 125.00 no
    N4 C22 H22B . . . 109.00 no
    C23 C22 H22A . . . 109.00 no
    C23 C22 H22B . . . 109.00 no
    H22A C22 H22B . . . 108.00 no
    N4 C22 H22A . . . 109.00 no
    C24 C23 H23 . . . 118.00 no
    C22 C23 H23 . . . 118.00 no
    C23 C24 H24 . . . 116.00 no
    C25 C24 H24 . . . 116.00 no
    C24 C25 H25B . . . 109.00 no
    C24 C25 H25C . . . 110.00 no
    C24 C25 H25A . . . 109.00 no
    H25A C25 H25C . . . 110.00 no
    H25B C25 H25C . . . 109.00 no
    H25A C25 H25B . . . 110.00 no
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
    C11 N1 C5 C10 . . . . -0.5(5) no
    C4 N1 C11 N2 . . . . 179.3(4) no
    C5 N1 C4 C3 . . . . -94.8(8) no
    C11 N1 C4 C3 . . . . 86.9(8) no
    C4 N1 C5 C6 . . . . 0.2(8) no
    C11 N1 C5 C6 . . . . 178.8(5) no
    C4 N1 C5 C10 . . . . -179.1(5) no
    C5 N1 C11 N2 . . . . 0.7(5) no
    C11 N2 C10 C9 . . . . -178.3(5) no
    C12 N2 C10 C9 . . . . 0.1(7) no
    C10 N2 C11 N1 . . . . -0.5(5) no
    C12 N2 C11 N1 . . . . -179.0(4) no
    C10 N2 C12 C13 . . . . 83.4(5) no
    C11 N2 C12 C13 . . . . -98.4(5) no
    C12 N2 C10 C5 . . . . 178.7(4) no
    C11 N2 C10 C5 . . . . 0.2(5) no
    C21 N3 C14 C13 . . . . -29.1(6) no
    C15 N3 C14 C13 . . . . 156.7(4) no
    C14 N3 C15 C16 . . . . -3.4(7) no
    C15 N3 C21 N4 . . . . -1.7(5) no
    C14 N3 C21 N4 . . . . -176.7(4) no
    C14 N3 C15 C20 . . . . 176.4(4) no
    C21 N3 C15 C20 . . . . 1.4(4) no
    C21 N3 C15 C16 . . . . -178.4(5) no
    C21 N4 C20 C15 . . . . -0.4(5) no
    C22 N4 C21 N3 . . . . -179.4(4) no
    C20 N4 C22 C23 . . . . 77.2(7) no
    C20 N4 C21 N3 . . . . 1.3(5) no
    C21 N4 C22 C23 . . . . -101.9(6) no
    C21 N4 C20 C19 . . . . -178.2(5) no
    C22 N4 C20 C19 . . . . 2.6(8) no
    C22 N4 C20 C15 . . . . -179.7(4) no
    C1 C2 C3 C4 . . . . 179(3) no
    C2 C3 C4 N1 . . . . -102.2(19) no
    C6 C5 C10 C9 . . . . -0.5(7) no
    C6 C5 C10 N2 . . . . -179.2(4) no
    C10 C5 C6 C7 . . . . -0.8(7) no
    N1 C5 C6 C7 . . . . -180.0(5) no
    N1 C5 C10 C9 . . . . 178.9(4) no
    N1 C5 C10 N2 . . . . 0.2(5) no
    C5 C6 C7 C8 . . . . 1.6(7) no
    C6 C7 C8 C9 . . . . -1.2(8) no
    C7 C8 C9 C10 . . . . -0.1(7) no
    C8 C9 C10 C5 . . . . 0.9(7) no
    C8 C9 C10 N2 . . . . 179.3(5) no
    N2 C12 C13 C14 . . . . -169.9(4) no
    C12 C13 C14 N3 . . . . -62.0(5) no
    N3 C15 C20 N4 . . . . -0.6(4) no
    N3 C15 C16 C17 . . . . -178.5(4) no
    C20 C15 C16 C17 . . . . 1.7(7) no
    C16 C15 C20 C19 . . . . -2.7(7) no
    N3 C15 C20 C19 . . . . 177.6(4) no
    C16 C15 C20 N4 . . . . 179.3(4) no
    C15 C16 C17 C18 . . . . -0.9(8) no
    C16 C17 C18 C19 . . . . 0.9(9) no
    C17 C18 C19 C20 . . . . -1.6(8) no
    C18 C19 C20 N4 . . . . 180.0(5) no
    C18 C19 C20 C15 . . . . 2.5(7) no
    N4 C22 C23 C24 . . . . -136.1(8) no
    C22 C23 C24 C25 . . . . -177.3(9) no
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
    O1 HW1 Br1 . 0.81(8) 2.54(8) 3.342(6) 171(8) yes
    O1 HW2 Br2 1_655 0.89(9) 2.45(8) 3.333(5) 171(7) yes
    C4 H4A Br2 2_666 0.97 2.81 3.773(4) 172 yes
    C4 H4B Br2 1_655 0.97 2.86 3.802(6) 164 yes
    C11 H11 Br1 . 0.93 2.76 3.536(4) 142 yes
    C12 H12A Br2 . 0.97 2.89 3.822(5) 161 yes
    C19 H19 Br2 2_555 0.93 2.92 3.816(5) 162 yes
    C21 H21 Br1 . 0.93 2.65 3.550(5) 162 yes
