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Acta Crystallogr Sect E Struct Rep Online. 2008 November 1; 64(Pt 11): o2136–o2137.
Published online 2008 October 18. doi:  10.1107/S160053680803095X
PMCID: PMC2959630

(E)-1,1′-Bis[(E)-but-2-en­yl]-3,3′-(propane-1,3-di­yl)bis­(1H-benzimidazol-3-ium) dibromide monohydrate

Abstract

The title compound, C25H30N4 2+·2Br·H2O, was synthesized from 1,1′-propyl­enedibenzimidazole and (E)-1-bromo­but-2-ene in dimethyl­formamide solution. The two benzimidazole ring systems are essentially planar, with maximum deviations of 0.011 (4) and 0.023 (3) Å. The dihedral angle between these two ring systems is 25.87 (15)°. The crystal structure is stabilized by inter­molecular O—H(...)Br and C—H(...)Br hydrogen-bonding inter­actions. Atmospheric water was incorporated into the crystal structure.

Related literature

For bond-length data, see: Allen et al. (1987 [triangle]). For general background, see: Sakai et al. (1989 [triangle]); Tidwell et al. (1993 [triangle]); Küçükbay et al. (1995 [triangle], 2001 [triangle]); Turner & Denny (1996 [triangle]); Hall et al. (1998 [triangle]). For related structures, see, for example: Öztürk et al. (2003 [triangle]); Akkurt et al. (2003 [triangle], 2006 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o2136-scheme1.jpg

Experimental

Crystal data

  • C25H30N4 2+·2Br·H2O
  • M r = 564.35
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2136-efi1.jpg
  • a = 8.7989 (9) Å
  • b = 11.1878 (13) Å
  • c = 14.8813 (14) Å
  • α = 106.381 (8)°
  • β = 96.490 (8)°
  • γ = 106.227 (8)°
  • V = 1319.9 (3) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 3.09 mm−1
  • T = 296 K
  • 0.53 × 0.45 × 0.31 mm

Data collection

  • Stoe IPDSII diffractometer
  • Absorption correction: integration (X-RED32; Stoe & Cie, 2002 [triangle]) T min = 0.291, T max = 0.447
  • 16109 measured reflections
  • 6181 independent reflections
  • 4101 reflections with I > 2σ(I)
  • R int = 0.063

Refinement

  • R[F 2 > 2σ(F 2)] = 0.054
  • wR(F 2) = 0.124
  • S = 1.05
  • 6181 reflections
  • 297 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.56 e Å−3
  • Δρmin = −0.41 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 [triangle]); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 [triangle]); program(s) used to solve structure: SIR97 (Altomare et al., 1999 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680803095X/sj2540sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680803095X/sj2540Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the diffractometer (purchased under grant F.279 of the University Research Fund). HK and NŞ thank İnönü University Research Fund (directed project BAPB-2007-46) for financial support for this study.

supplementary crystallographic information

Comment

In the light of the general importance of benzimidazole compounds, the study of bisbenzimidazoles and their related derivatives has remained an active area of research despite extensive investigation. They are present in various naturally occurring drugs such as omeprazole, astemizole and emedastine difumarate (Sakai et al., 1989). Substituted benzimidazole compounds are established pharmacophores in parasitic chemotheraphy. They also show antiviral (Tidwell et al., 1993), antimicrobial (Küçükbay et al., 1995; Küçükbay et al., 2001), antitumor (Turner and Denny, 1996), antihistaminic, anticoagulant and anti-inflammatory activities (Hall et al., 1998). The objective of this study was to elucidate the crystal structure of the title compound (I) and to compare the results obtained with our previous studies on related bis-benzimidazole compounds (Öztürk et al., 2003; Akkurt et al., 2003; Akkurt et al., 2006).

In (I) (Fig. 1), the bond lengths and angles are generally within normal ranges (Allen et al., 1987). The two benzimidazole ring systems of (I), A (N1/N2/C5–C11) and B (N3/N4/C15–C21), are essentially planar, with maximum deviations of 0.011 (4) Å for C10 and -0.10 (5) Å for C11 in A, and 0.023 (3) Å for N3 and 0.016 (5) Å for C19 in B. The dihedral angle between these two ring systems A and B is 25.87 (15) °. This angle is 31.84 (11)° in 3,30-bis(cyclohexylmethyl)- 1,10-propylenedibenzimidazolium dibromide monohydrate (Akkurt et al., 2006) and 88.42 (4)° in 3,30-bis(3- cyanopropyl)-1,10-propylene- di(benzimidazolium) dichloride dihydrate (Akkurt et al., 2003). This divergence may be due to the interactions of the different substituents bounded to the benzimidazole ring system.

The crystal structure of (I) is stabilized by inter and intramolecular O—H···Br and C—H···Br hydrogen bonding interactions, involving the H atoms of the water molecule (Table 1 and Fig. 2).

Experimental

A mixture of 1,1'-propylenedibenzimidazole (0.9 g, 3.26 mmol) and (E)-1-bromobut-2-ene (1.2 g, 6.78 mmol) in dimethylformamide (5 ml) was heated under reflux for 3 h. The mixture was then cooled and the volatiles were removed in vacuo. The residue was crystallized from a DMF/EtOH (1:3) mixture [Yield: 1.39 g, 78%. Mp. 479–481°K].

Analysis, calculated for C25H32N4OBr2: C53.19, H 5.67, N 9.93%; found: C 53.95, H 5.42, N 10.11%. 1H-NMR (DMSO-d6): δ (p.p.m.) 8.24 (s, 2-CH, 2H), 2.64 (t, bridge, 2H), 4.83 (t, bridge, 4H), 1.86 (d, methyl, 6H), 5.14 (d, methylene, 4H), 5.77 (m, =CH, 4H), 7.70–8.05 (m, Ar—H, 8H). 13C-NMR (DMSO-d6): δ (p.p.m.) 13.28, 17.56, 28.28, 43.70, 48.44, 113.74, 122.22, 123.37, 126.50, 130.89, 131.52, 132.89, 142.18.

Refinement

The H atoms of the water molecule were located from a difference Fourier map and refined freely. The C-bound H atoms were located geometrically, with C—H = 0.93 - 0.97 Å, and refined using a riding model, with Uiso(H) = 1.2Ueq(Caromatic and Cmethylene) or 1.5Ueq(Cmethyl). The C atoms of both –CH2(CH)2CH3 groups in (I) show very high thermal parameters but a suitable disorder model could not be found to separate discrete disorder components

Figures

Fig. 1.
An ORTEP view of (I), with the atom-numbering scheme and 10% probability displacement ellipsoids.
Fig. 2.
The packing and hydrogen bonding of (I), viewed down the b axis. Hydrogen bonds are drawn as dashed lines and H atoms not involved in these interactions have been omitted for clarity.

Crystal data

C25H30N42+·2Br·H2OZ = 2
Mr = 564.35F(000) = 576
Triclinic, P1Dx = 1.420 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.7989 (9) ÅCell parameters from 25470 reflections
b = 11.1878 (13) Åθ = 2.0–28.0°
c = 14.8813 (14) ŵ = 3.09 mm1
α = 106.381 (8)°T = 296 K
β = 96.490 (8)°Prismatic plate, light yellow
γ = 106.227 (8)°0.53 × 0.45 × 0.31 mm
V = 1319.9 (3) Å3

Data collection

Stoe IPDSII diffractometer6181 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus4101 reflections with I > 2σ(I)
plane graphiteRint = 0.063
Detector resolution: 6.67 pixels mm-1θmax = 27.7°, θmin = 2.5°
ω scansh = −11→11
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)k = −14→13
Tmin = 0.291, Tmax = 0.447l = −18→19
16109 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124H atoms treated by a mixture of independent and constrained refinement
S = 1.05w = 1/[σ2(Fo2) + (0.0416P)2 + 0.9807P] where P = (Fo2 + 2Fc2)/3
6181 reflections(Δ/σ)max < 0.001
297 parametersΔρmax = 0.56 e Å3
0 restraintsΔρmin = −0.41 e Å3

Special details

Geometry. 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
Refinement. 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
N10.7390 (4)0.6064 (4)0.4072 (2)0.0525 (10)
N20.4931 (4)0.5116 (3)0.3227 (2)0.0495 (10)
N30.1559 (4)0.3113 (3)0.0400 (2)0.0463 (10)
N40.2504 (4)0.1820 (4)−0.0600 (2)0.0557 (11)
C11.1336 (19)0.851 (2)0.3031 (16)0.400 (19)
C21.0601 (14)0.774 (2)0.3445 (13)0.292 (12)
C30.9949 (10)0.7489 (12)0.4033 (10)0.177 (6)
C40.9166 (5)0.6413 (6)0.4322 (3)0.0707 (18)
C50.6392 (5)0.6485 (4)0.4651 (3)0.0485 (12)
C60.6724 (5)0.7321 (4)0.5592 (3)0.0572 (14)
C70.5407 (6)0.7523 (5)0.5946 (3)0.0661 (16)
C80.3830 (6)0.6909 (5)0.5413 (3)0.0673 (17)
C90.3504 (5)0.6076 (4)0.4486 (3)0.0559 (14)
C100.4821 (5)0.5886 (4)0.4116 (2)0.0451 (11)
C110.6481 (5)0.5246 (4)0.3234 (3)0.0546 (14)
C120.3576 (5)0.4279 (4)0.2430 (3)0.0524 (12)
C130.3047 (5)0.5057 (4)0.1841 (3)0.0536 (12)
C140.1475 (5)0.4283 (4)0.1120 (3)0.0547 (14)
C150.0246 (5)0.2004 (4)−0.0130 (2)0.0462 (11)
C16−0.1379 (5)0.1681 (5)−0.0101 (3)0.0607 (16)
C17−0.2356 (6)0.0474 (5)−0.0719 (4)0.0730 (17)
C18−0.1753 (7)−0.0361 (5)−0.1343 (4)0.0756 (17)
C19−0.0147 (6)−0.0054 (5)−0.1380 (3)0.0692 (18)
C200.0849 (5)0.1169 (4)−0.0768 (3)0.0528 (14)
C210.2866 (5)0.2959 (4)0.0079 (3)0.0520 (14)
C220.3684 (7)0.1338 (7)−0.1103 (3)0.084 (2)
C230.3596 (8)0.1486 (7)−0.2051 (4)0.094 (3)
C240.3622 (10)0.0582 (8)−0.2808 (5)0.116 (3)
C250.3606 (14)0.0664 (10)−0.3775 (6)0.162 (5)
O10.5845 (5)0.2069 (5)0.1612 (4)0.0878 (16)
Br10.70894 (5)0.46584 (5)0.08608 (3)0.0654 (2)
Br2−0.05435 (5)0.30445 (5)0.30568 (3)0.0648 (2)
H1A1.161600.800900.247500.5960*
H1B1.230300.914100.346400.5960*
H1C1.064300.896300.284200.5960*
H21.057700.691400.305800.3530*
H30.993300.826600.446700.2120*
H4A0.950900.664100.500900.0840*
H4B0.947700.565700.401200.0840*
H60.777200.771800.595800.0680*
H70.557600.809400.656700.0800*
H80.297800.706500.569000.0810*
H90.245200.566200.412700.0670*
H110.687100.482200.272400.0660*
H12A0.267100.386600.267900.0630*
H12B0.389100.358500.202100.0630*
H13A0.292500.584100.227000.0650*
H13B0.388900.533900.150500.0650*
H14A0.062900.401100.145700.0660*
H14B0.117900.485300.079800.0660*
H16−0.178500.224700.031300.0730*
H17−0.345700.02090−0.072000.0870*
H18−0.24680−0.11630−0.175500.0910*
H190.02510−0.06320−0.179000.0830*
H210.389800.357700.030500.0620*
H22A0.476800.18260−0.072200.1010*
H22B0.347400.04150−0.116900.1010*
H230.351800.22730−0.211200.1130*
H240.36530−0.02080−0.273200.1390*
H25A0.36370−0.01500−0.419800.2430*
H25B0.453400.13740−0.376100.2430*
H25C0.263800.08230−0.399800.2430*
HW10.625 (9)0.268 (7)0.143 (5)0.11 (3)*
HW20.677 (10)0.224 (7)0.201 (5)0.12 (3)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0407 (17)0.070 (2)0.0457 (17)0.0218 (17)0.0100 (13)0.0135 (16)
N20.0431 (18)0.058 (2)0.0410 (16)0.0144 (15)0.0074 (13)0.0091 (14)
N30.0391 (16)0.055 (2)0.0418 (16)0.0164 (15)0.0081 (12)0.0107 (14)
N40.052 (2)0.074 (2)0.0436 (17)0.0306 (18)0.0127 (14)0.0120 (17)
C10.177 (14)0.60 (4)0.59 (4)0.059 (18)0.041 (18)0.53 (3)
C20.089 (8)0.50 (3)0.40 (2)0.047 (12)0.045 (10)0.37 (2)
C30.057 (5)0.233 (12)0.288 (14)0.033 (6)0.035 (6)0.173 (11)
C40.043 (2)0.108 (4)0.061 (3)0.032 (3)0.0097 (19)0.021 (3)
C50.044 (2)0.058 (2)0.045 (2)0.0184 (19)0.0102 (16)0.0173 (18)
C60.055 (2)0.068 (3)0.043 (2)0.024 (2)0.0019 (17)0.0093 (19)
C70.074 (3)0.079 (3)0.046 (2)0.037 (3)0.014 (2)0.009 (2)
C80.063 (3)0.087 (3)0.057 (3)0.038 (3)0.023 (2)0.014 (2)
C90.046 (2)0.067 (3)0.057 (2)0.021 (2)0.0142 (18)0.020 (2)
C100.045 (2)0.048 (2)0.0401 (18)0.0142 (17)0.0084 (15)0.0125 (16)
C110.046 (2)0.069 (3)0.043 (2)0.018 (2)0.0134 (16)0.0088 (19)
C120.046 (2)0.050 (2)0.047 (2)0.0062 (18)0.0038 (16)0.0061 (17)
C130.052 (2)0.054 (2)0.046 (2)0.0144 (19)0.0048 (17)0.0080 (18)
C140.051 (2)0.063 (3)0.046 (2)0.024 (2)0.0077 (17)0.0073 (18)
C150.046 (2)0.053 (2)0.0389 (18)0.0184 (18)0.0054 (15)0.0133 (16)
C160.042 (2)0.073 (3)0.065 (3)0.020 (2)0.0046 (19)0.021 (2)
C170.046 (3)0.076 (3)0.088 (3)0.011 (2)−0.003 (2)0.029 (3)
C180.072 (3)0.059 (3)0.071 (3)0.006 (3)−0.021 (2)0.013 (2)
C190.080 (4)0.062 (3)0.055 (2)0.031 (3)−0.005 (2)0.003 (2)
C200.052 (2)0.063 (3)0.043 (2)0.023 (2)0.0033 (17)0.0151 (18)
C210.040 (2)0.068 (3)0.043 (2)0.0157 (19)0.0085 (15)0.0129 (19)
C220.073 (3)0.117 (5)0.063 (3)0.051 (3)0.025 (2)0.007 (3)
C230.100 (5)0.096 (4)0.080 (4)0.030 (4)0.044 (3)0.013 (3)
C240.159 (7)0.124 (6)0.082 (4)0.058 (5)0.042 (4)0.042 (4)
C250.221 (11)0.175 (9)0.114 (6)0.072 (8)0.071 (7)0.061 (6)
O10.054 (2)0.091 (3)0.103 (3)0.006 (2)0.007 (2)0.030 (2)
Br10.0531 (3)0.0932 (4)0.0649 (3)0.0309 (3)0.0197 (2)0.0390 (3)
Br20.0507 (3)0.0840 (4)0.0557 (3)0.0243 (2)0.0134 (2)0.0140 (2)

Geometric parameters (Å, °)

O1—HW20.89 (9)C23—C241.292 (10)
O1—HW10.81 (8)C24—C251.466 (12)
N1—C111.324 (5)C1—H1C0.9600
N1—C41.476 (6)C1—H1A0.9600
N1—C51.382 (6)C1—H1B0.9600
N2—C111.329 (6)C2—H20.9300
N2—C121.461 (5)C3—H30.9300
N2—C101.391 (4)C4—H4A0.9700
N3—C211.330 (6)C4—H4B0.9700
N3—C141.466 (5)C6—H60.9300
N3—C151.392 (5)C7—H70.9300
N4—C221.480 (7)C8—H80.9300
N4—C201.391 (6)C9—H90.9300
N4—C211.312 (6)C11—H110.9300
C1—C21.27 (3)C12—H12A0.9700
C2—C31.16 (2)C12—H12B0.9700
C3—C41.416 (15)C13—H13A0.9700
C5—C61.392 (6)C13—H13B0.9700
C5—C101.388 (6)C14—H14A0.9700
C6—C71.374 (7)C14—H14B0.9700
C7—C81.392 (7)C16—H160.9300
C8—C91.375 (6)C17—H170.9300
C9—C101.381 (6)C18—H180.9300
C12—C131.519 (6)C19—H190.9300
C13—C141.512 (6)C21—H210.9300
C15—C161.382 (7)C22—H22B0.9700
C15—C201.395 (6)C22—H22A0.9700
C16—C171.371 (8)C23—H230.9300
C17—C181.384 (8)C24—H240.9300
C18—C191.369 (8)C25—H25C0.9600
C19—C201.384 (7)C25—H25A0.9600
C22—C231.462 (8)C25—H25B0.9600
Br1···C213.550 (5)C19···H1Ci2.8300
Br1···O13.342 (6)C21···H12B2.7500
Br1···C113.536 (4)C21···H13B2.7300
Br1···C14i3.696 (4)C22···H193.0600
Br1···C21i3.335 (5)HW1···H112.4900
Br1···N3i3.555 (3)HW1···Br12.54 (8)
Br2···O1ii3.333 (5)HW1···H16iii2.5800
Br1···HW12.54 (8)H1C···C19i2.8300
Br1···H112.7600H2···H4B2.3700
Br1···H212.6500HW2···Br2iii2.45 (8)
Br1···H16iii3.0600H4A···H62.5200
Br1···H14Bi3.1400H4A···C62.9100
Br1···H21i3.2000H4A···Br2iv2.8100
Br2···H14A3.0500H4B···H22.3700
Br2···HW2ii2.45 (8)H4B···H112.5700
Br2···H4Bii2.8600H4B···Br2iii2.8600
Br2···H4Aiv2.8100H6···Br2iv3.1400
Br2···H6iv3.1400H6···C43.0400
Br2···H8v2.9900H6···H4A2.5200
Br2···H19vi2.9200H8···Br2v2.9900
Br2···H93.1900H9···H12A2.5700
Br2···H12A2.8900H9···C122.9900
O1···Br2iii3.333 (5)H9···Br23.1900
O1···C17vi3.369 (8)H11···Br12.7600
O1···Br13.342 (6)H11···H4B2.5700
O1···H12B2.7400H11···O12.8800
O1···H22Bvii2.9200H11···HW12.4900
O1···H112.8800H11···H12B2.5300
O1···H18vi2.9100H12A···C92.9400
O1···H17vi2.6700H12A···H92.5700
N1···N22.177 (5)H12A···Br22.8900
N2···N12.177 (5)H12A···H14A2.4800
N3···Br1i3.555 (3)H12B···N32.8000
N3···N42.176 (5)H12B···O12.7400
N4···N32.176 (5)H12B···H18vi2.5400
N3···H12B2.8000H12B···H212.5500
C1···C19i3.60 (2)H12B···H112.5300
C5···C9iv3.473 (6)H12B···C212.7500
C8···C11iv3.526 (7)H13A···C103.0300
C9···C5iv3.473 (6)H13B···H212.2600
C11···C8iv3.526 (7)H13B···C212.7300
C11···Br13.536 (4)H14A···Br23.0500
C12···C213.300 (6)H14A···C162.9000
C14···Br1i3.696 (4)H14A···H12A2.4800
C15···C18vi3.594 (7)H14A···H162.5000
C15···C19vi3.538 (6)H14B···Br1i3.1400
C16···C19vi3.596 (7)H16···C142.9800
C17···O1vi3.369 (8)H16···Br1ii3.0600
C18···C20vi3.572 (7)H16···HW1ii2.5800
C18···C15vi3.594 (7)H16···H14A2.5000
C19···C16vi3.596 (7)H17···O1vi2.6700
C19···C15vi3.538 (6)H18···H12Bvi2.5400
C19···C1i3.60 (2)H18···O1vi2.9100
C20···C18vi3.572 (7)H19···C223.0600
C21···Br13.550 (5)H19···Br2vi2.9200
C21···C123.300 (6)H21···Br12.6500
C21···Br1i3.335 (5)H21···C132.7300
C4···H63.0400H21···H12B2.5500
C6···H4A2.9100H21···H13B2.2600
C9···H12A2.9400H21···H22A2.4800
C10···H13A3.0300H21···Br1i3.2000
C12···H92.9900H22A···H212.4800
C13···H212.7300H22B···C193.0400
C14···H162.9800H22B···H242.2700
C16···H14A2.9000H22B···O1vii2.9200
C19···H22B3.0400H24···H22B2.2700
HW1—O1—HW291 (7)N1—C4—H4B109.00
C4—N1—C11124.1 (4)C3—C4—H4B109.00
C5—N1—C11108.5 (4)H4A—C4—H4B108.00
C4—N1—C5127.4 (3)C3—C4—H4A109.00
C10—N2—C11108.2 (3)C5—C6—H6122.00
C11—N2—C12125.7 (3)C7—C6—H6122.00
C10—N2—C12126.1 (4)C6—C7—H7119.00
C14—N3—C15125.6 (4)C8—C7—H7119.00
C15—N3—C21107.6 (3)C9—C8—H8119.00
C14—N3—C21126.6 (4)C7—C8—H8119.00
C20—N4—C21108.8 (4)C10—C9—H9122.00
C20—N4—C22126.5 (4)C8—C9—H9122.00
C21—N4—C22124.7 (4)N1—C11—H11125.00
C1—C2—C3155 (2)N2—C11—H11125.00
C2—C3—C4142.0 (16)N2—C12—H12A109.00
N1—C4—C3111.2 (6)N2—C12—H12B109.00
N1—C5—C10106.8 (3)C13—C12—H12B109.00
C6—C5—C10121.5 (4)H12A—C12—H12B108.00
N1—C5—C6131.7 (4)C13—C12—H12A109.00
C5—C6—C7115.8 (4)C12—C13—H13A109.00
C6—C7—C8122.6 (4)C14—C13—H13A109.00
C7—C8—C9121.4 (5)C14—C13—H13B109.00
C8—C9—C10116.4 (4)C12—C13—H13B109.00
N2—C10—C5106.3 (4)H13A—C13—H13B108.00
C5—C10—C9122.1 (3)N3—C14—H14B109.00
N2—C10—C9131.6 (4)C13—C14—H14A109.00
N1—C11—N2110.2 (4)C13—C14—H14B109.00
N2—C12—C13111.9 (4)H14A—C14—H14B108.00
C12—C13—C14113.4 (4)N3—C14—H14A109.00
N3—C14—C13113.3 (4)C17—C16—H16122.00
N3—C15—C16131.2 (4)C15—C16—H16122.00
C16—C15—C20122.0 (4)C16—C17—H17119.00
N3—C15—C20106.8 (4)C18—C17—H17119.00
C15—C16—C17116.0 (4)C19—C18—H18119.00
C16—C17—C18121.9 (5)C17—C18—H18119.00
C17—C18—C19122.7 (5)C18—C19—H19122.00
C18—C19—C20115.9 (5)C20—C19—H19122.00
N4—C20—C15105.8 (4)N3—C21—H21125.00
N4—C20—C19132.7 (4)N4—C21—H21125.00
C15—C20—C19121.4 (4)N4—C22—H22B109.00
N3—C21—N4110.9 (4)C23—C22—H22A109.00
N4—C22—C23111.9 (5)C23—C22—H22B109.00
C22—C23—C24123.5 (7)H22A—C22—H22B108.00
C23—C24—C25127.2 (9)N4—C22—H22A109.00
C2—C1—H1A110.00C24—C23—H23118.00
C2—C1—H1B109.00C22—C23—H23118.00
H1A—C1—H1B109.00C23—C24—H24116.00
H1A—C1—H1C109.00C25—C24—H24116.00
H1B—C1—H1C109.00C24—C25—H25B109.00
C2—C1—H1C109.00C24—C25—H25C110.00
C3—C2—H2103.00C24—C25—H25A109.00
C1—C2—H2103.00H25A—C25—H25C110.00
C2—C3—H3109.00H25B—C25—H25C109.00
C4—C3—H3109.00H25A—C25—H25B110.00
N1—C4—H4A109.00
C11—N1—C5—C10−0.5 (5)C22—N4—C20—C192.6 (8)
C4—N1—C11—N2179.3 (4)C22—N4—C20—C15−179.7 (4)
C5—N1—C4—C3−94.8 (8)C1—C2—C3—C4179 (3)
C11—N1—C4—C386.9 (8)C2—C3—C4—N1−102.2 (19)
C4—N1—C5—C60.2 (8)C6—C5—C10—C9−0.5 (7)
C11—N1—C5—C6178.8 (5)C6—C5—C10—N2−179.2 (4)
C4—N1—C5—C10−179.1 (5)C10—C5—C6—C7−0.8 (7)
C5—N1—C11—N20.7 (5)N1—C5—C6—C7−180.0 (5)
C11—N2—C10—C9−178.3 (5)N1—C5—C10—C9178.9 (4)
C12—N2—C10—C90.1 (7)N1—C5—C10—N20.2 (5)
C10—N2—C11—N1−0.5 (5)C5—C6—C7—C81.6 (7)
C12—N2—C11—N1−179.0 (4)C6—C7—C8—C9−1.2 (8)
C10—N2—C12—C1383.4 (5)C7—C8—C9—C10−0.1 (7)
C11—N2—C12—C13−98.4 (5)C8—C9—C10—C50.9 (7)
C12—N2—C10—C5178.7 (4)C8—C9—C10—N2179.3 (5)
C11—N2—C10—C50.2 (5)N2—C12—C13—C14−169.9 (4)
C21—N3—C14—C13−29.1 (6)C12—C13—C14—N3−62.0 (5)
C15—N3—C14—C13156.7 (4)N3—C15—C20—N4−0.6 (4)
C14—N3—C15—C16−3.4 (7)N3—C15—C16—C17−178.5 (4)
C15—N3—C21—N4−1.7 (5)C20—C15—C16—C171.7 (7)
C14—N3—C21—N4−176.7 (4)C16—C15—C20—C19−2.7 (7)
C14—N3—C15—C20176.4 (4)N3—C15—C20—C19177.6 (4)
C21—N3—C15—C201.4 (4)C16—C15—C20—N4179.3 (4)
C21—N3—C15—C16−178.4 (5)C15—C16—C17—C18−0.9 (8)
C21—N4—C20—C15−0.4 (5)C16—C17—C18—C190.9 (9)
C22—N4—C21—N3−179.4 (4)C17—C18—C19—C20−1.6 (8)
C20—N4—C22—C2377.2 (7)C18—C19—C20—N4180.0 (5)
C20—N4—C21—N31.3 (5)C18—C19—C20—C152.5 (7)
C21—N4—C22—C23−101.9 (6)N4—C22—C23—C24−136.1 (8)
C21—N4—C20—C19−178.2 (5)C22—C23—C24—C25−177.3 (9)

Symmetry codes: (i) −x+1, −y+1, −z; (ii) x−1, y, z; (iii) x+1, y, z; (iv) −x+1, −y+1, −z+1; (v) −x, −y+1, −z+1; (vi) −x, −y, −z; (vii) −x+1, −y, −z.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—HW1···Br10.81 (8)2.54 (8)3.342 (6)171 (8)
O1—HW2···Br2iii0.89 (9)2.45 (8)3.333 (5)171 (7)
C4—H4A···Br2iv0.972.813.773 (4)172
C4—H4B···Br2iii0.972.863.802 (6)164
C11—H11···Br10.932.763.536 (4)142
C12—H12A···Br20.972.893.822 (5)161
C19—H19···Br2vi0.932.923.816 (5)162
C21—H21···Br10.932.653.550 (5)162

Symmetry codes: (iii) x+1, y, z; (iv) −x+1, −y+1, −z+1; (vi) −x, −y, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2540).

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