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Acta Cryst. (2008). E64, o2019-o2020    [ doi:10.1107/S1600536808030432 ]

1,3-Bis(3-phenylpropyl)benzimidazolium bromide monohydrate

M. Akkurt, S. Karaca, Ü. Yilmaz, H. Küçükbay and O. Büyükgüngör

Abstract top

In the title compound, C25H27N2+·Br-·H2O, the benzimidazole unit is essentially planar, with a maximum deviation of 0.020 (6) Å. The benzimidazole unit makes dihedral angles of 83.6 (3) and 81.0 (3)° with the two terminal phenyl rings. The dihedral angle between the phenyl rings is 58.5 (4)°. In the crystal structure, there are C-H...O hydrogen bonds, a C-H...[pi] interaction between a phenyl H atom and the phenyl ring of a neighbouring molecule, and a [pi]-[pi] interaction [3.512 (3) Å] between the centroids of the five-membered ring and the benzene ring of the benzimidazole unit of an adjacent molecule.

Comment top

Benzimidazole and related heterocyclic compounds have been extensively investigated because of their versatile pharmacological activity. They are also present in various naturally occurring drugs such as omeprazole, astemizole andemedastine difumarate (Sakai et al., 1989). Substituted benzimidazole moieties are estabilished pharmacophores in parasitic chemotheraphy. In some previous papers (Küçükbay et al., 2001, 2003, 2004), we reported the synthesis and antimicrobial activity of some benzimidazole derivatives. The objective of this study was to elucidate the crystal structure of the title compound, (I).

In the title molecule (I) (Fig. 1), the values of the geometric parameters are comparable with those of previously reported structures (Akkurt et al., 2004, 2005, 2007; Pınar et al., 2006; Yıldırım et al., 2005; Karaca et al., 2005). The benzimidazole unit (N1/N2/C1–C7) is essentially planar, with a maximum deviation of 0.020 (6) Å for C7 from the least-squares plane defined by the nine constituent atoms. The benzimidazole unit makes the dihedral angles of 83.6 (3) and 81.0 (3)° with the two terminal phenyl rings (C11–C16) and (C20–C25), respectively. The dihedral angle between the phenyl rings is 58.5 (4)°.

Molecular conformation is stabilized by intramolecular C—H···O hydrogen bonding interactions. The molecular packing (Fig. 2) is stabilized by a C—H···π interaction between a phenyl H atom and the phenyl ring of neighbouring molecules, with a C24—H24···Cg1ii separation of 2.84 Å [Table 1; Cg1 is the C11–C16 phenyl ring, symmetry code: (ii) x, -y + 1/2, z + 1/2]. In the crystal packing, there is also a π–π interaction with a distance of 3.512 (3) Å between the centroids of the five-membered ring (N1/N2/C1/C6/C7) (centroid Cg2) and the benzene ring (C1–C6) (centroid Cg3) of the benzimidazole unit of the adjacent molecule.

Related literature top

For related literature, see: Akkurt et al. (2004, 2005, 2007); Küçükbay et al. (2001, 2003, 2004); Karaca et al. (2005); Pınar et al. (2006); Sakai et al. (1989); Yıldırım et al. (2005). It would be much more useful to readers if the "Related literature" section had some kind of simple sub-division, so that, instead of just "For related literature, see···" it said, for example, "For general background, see···. For related structures, see···.? etc. Please revise this section as indicated. Cg1 is the centriod of the C11–C16 phenyl ring.

Experimental top

A solution of 1-(3-phenylpropyl)benzimidazole (4.20 g,17.80 mmol) and Ph(CH2)3Br (2.70 ml, 17.85 mmol) was refluxed in DMF for 4 h. The mixture was then cooled and the volatiles were removed from the filtrate in vacuo. The residue obtained was then crytallized from EtOH/Et2O(1:5) (yield 6.50 g, 84%; m.p. 376–377 K). 1H-NMR (DMSO-d6): δ (p.p.m.) 2.26 (p, CH2, 4H), 2.73 (t, CH2—Ar, 4H), 4.55 (t, CH2—N, 4H), 7.14–8.13 (m, Ar—H, 14H), 9.99 (s, >CH, 1H). 13C-NMR (DMSO-d6): δ 30.5, 32.4, 47.0, 114.2, 126.5, 126.9, 128.7, 131.6, 141.4, 142.7. Analysis calculated for C25H29N2OBr: C 66.23, H 6.40, N 6.18%; found: C 65.99, H 6.13, N 6.10%.

Refinement top

Water H atoms were found in a difference Fourier map and distance restraints [O—H = 0.84 (9) and H···H = 1.37 (9) Å] were used to obtain reasonable values for O–H distances and H—O—H angles, with Uiso(H) = 1.5Ueq(O). Other H atoms were positioned to the ideal geometric positions and refined with a riding model, with C—H = 0.93 and 0.97 Å, and with Uiso = 1.2Ueq(C).

Computing details top

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

Figures top
[Figure 1] Fig. 1. The title molecule (I), with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level.
[Figure 2] Fig. 2. The crystal packing diagram of (I), down the b axis. Dashed lines indicate hydrogen contacts. H atoms not involved in hydrogen bonding have been omitted for clarity.
1,3-Bis(3-phenylpropyl)benzimidazolium bromide monohydrate top
Crystal data top
C25H27N2+·Br−·H2OF(000) = 944
Mr = 453.40Dx = 1.300 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 13886 reflections
a = 14.1933 (8) Åθ = 1.4–28.0°
b = 11.4594 (3) ŵ = 1.79 mm−1
c = 18.3014 (10) ÅT = 295 K
β = 128.916 (3)°Block, colourless
V = 2316.1 (2) Å30.71 × 0.63 × 0.54 mm
Z = 4
Data collection top
Stoe IPDS II
diffractometer		5283 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus2688 reflections with I > 2σ(I)
plane graphiteRint = 0.071
Detector resolution: 6.67 pixels mm-1θmax = 27.6°, θmin = 1.8°
ω scansh = −18→18
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)		k = −13→14
Tmin = 0.363, Tmax = 0.444l = −23→23
18735 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.065Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.173H atoms treated by a mixture of independent and constrained refinement
S = 0.99 w = 1/[σ2(Fo2) + (0.0827P)2]
where P = (Fo2 + 2Fc2)/3
5283 reflections(Δ/σ)max < 0.001
268 parametersΔρmax = 0.47 e Å−3
3 restraintsΔρmin = −0.24 e Å−3
Crystal data top
C25H27N2+·Br−·H2OV = 2316.1 (2) Å3
Mr = 453.40Z = 4
Monoclinic, P21/cMo Kα radiation
a = 14.1933 (8) ŵ = 1.79 mm−1
b = 11.4594 (3) ÅT = 295 K
c = 18.3014 (10) Å0.71 × 0.63 × 0.54 mm
β = 128.916 (3)°
Data collection top
Stoe IPDS II
diffractometer		5283 independent reflections
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)		2688 reflections with I > 2σ(I)
Tmin = 0.363, Tmax = 0.444Rint = 0.071
18735 measured reflectionsθmax = 27.6°
Refinement top
R[F2 > 2σ(F2)] = 0.065H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.173Δρmax = 0.47 e Å−3
S = 0.99Δρmin = −0.24 e Å−3
5283 reflectionsAbsolute structure: ?
268 parametersFlack parameter: ?
3 restraintsRogers parameter: ?
Special details top

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) top
xyzUiso*/Ueq
N1−0.1093 (3)0.1691 (3)0.9193 (2)0.0541 (10)
N2−0.1505 (3)0.0103 (3)0.8391 (2)0.0539 (11)
C1−0.1415 (3)0.0860 (3)0.9554 (3)0.0514 (11)
C2−0.1469 (4)0.0912 (4)1.0285 (3)0.0622 (14)
C3−0.1784 (4)−0.0099 (4)1.0477 (3)0.0753 (17)
C4−0.2034 (4)−0.1121 (4)0.9973 (3)0.0742 (17)
C5−0.1995 (4)−0.1173 (3)0.9243 (3)0.0645 (16)
C6−0.1673 (3)−0.0157 (3)0.9049 (3)0.0505 (11)
C7−0.1159 (4)0.1196 (3)0.8509 (3)0.0587 (12)
C8−0.1677 (4)−0.0701 (4)0.7691 (3)0.0700 (17)
C9−0.3031 (5)−0.0933 (4)0.6894 (3)0.0853 (19)
C10−0.3233 (6)−0.1767 (6)0.6209 (4)0.105 (2)
C11−0.4522 (5)−0.2161 (5)0.5455 (4)0.0905 (19)
C12−0.5522 (5)−0.1513 (5)0.5160 (4)0.102 (2)
C13−0.6656 (6)−0.1874 (7)0.4419 (4)0.107 (3)
C14−0.6809 (8)−0.2866 (8)0.3982 (5)0.121 (3)
C15−0.5849 (10)−0.3547 (7)0.4275 (6)0.128 (4)
C16−0.4716 (7)−0.3209 (6)0.5006 (6)0.113 (3)
C17−0.0775 (4)0.2925 (3)0.9491 (3)0.0652 (16)
C18−0.1947 (5)0.3644 (4)0.8951 (4)0.0844 (19)
C19−0.1744 (5)0.4916 (4)0.9136 (4)0.085 (2)
C20−0.2942 (5)0.5556 (4)0.8583 (4)0.079 (2)
C21−0.3563 (8)0.5820 (7)0.7649 (5)0.126 (3)
C22−0.4712 (9)0.6297 (8)0.7129 (6)0.166 (4)
C23−0.5191 (7)0.6575 (6)0.7529 (8)0.134 (4)
C24−0.4537 (8)0.6398 (7)0.8464 (8)0.132 (4)
C25−0.3441 (6)0.5865 (5)0.8976 (5)0.093 (2)
O10.0138 (8)0.3343 (4)0.8276 (5)0.145 (3)
Br10.01170 (5)0.12751 (4)0.69968 (4)0.0869 (2)
H2−0.130100.159401.062300.0750*
H3−0.18330−0.010501.096000.0900*
H4−0.22340−0.179101.013600.0890*
H5−0.21740−0.185300.890000.0780*
H7−0.098300.157400.815800.0700*
H8A−0.12700−0.143300.799300.0850*
H8B−0.13160−0.036900.743100.0850*
H9A−0.33960−0.122900.716100.1020*
H9B−0.34280−0.020400.657900.1020*
H10A−0.27450−0.245200.654500.1260*
H10B−0.29360−0.142500.590400.1260*
H12−0.54230−0.082400.547000.1230*
H13−0.73240−0.142200.421800.1270*
H14−0.75850−0.309600.346800.1460*
H15−0.59700−0.425000.397300.1540*
H16−0.40610−0.368400.520800.1360*
H17A−0.025400.321600.935900.0780*
H17B−0.034400.298901.016100.0780*
H18A−0.240300.351100.828400.1010*
H18B−0.243500.336900.911900.1010*
H19A−0.127000.520500.895900.1020*
H19B−0.129200.506100.980100.1020*
H21−0.321000.567800.736800.1510*
H22−0.515000.642200.648800.2000*
H23−0.596600.688900.717700.1610*
H24−0.484600.664500.876000.1580*
H25−0.303100.571200.960900.1110*
HW1−0.042 (7)0.364 (8)0.775 (4)0.2170*
HW20.071 (6)0.383 (7)0.854 (7)0.2170*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0533 (19)0.0500 (15)0.0617 (19)−0.0075 (14)0.0374 (17)−0.0040 (15)
N20.0536 (19)0.0543 (17)0.0612 (19)−0.0002 (14)0.0396 (17)−0.0013 (14)
C10.038 (2)0.0523 (19)0.054 (2)0.0024 (16)0.0242 (18)0.0012 (17)
C20.059 (3)0.070 (2)0.058 (2)−0.002 (2)0.037 (2)−0.0056 (19)
C30.079 (3)0.094 (3)0.065 (3)0.001 (3)0.051 (3)0.010 (2)
C40.079 (3)0.070 (3)0.080 (3)−0.003 (2)0.053 (3)0.015 (2)
C50.067 (3)0.052 (2)0.074 (3)−0.004 (2)0.044 (2)0.001 (2)
C60.043 (2)0.0499 (19)0.057 (2)0.0042 (16)0.0307 (19)0.0045 (17)
C70.054 (2)0.056 (2)0.069 (2)−0.0047 (19)0.040 (2)0.004 (2)
C80.078 (3)0.071 (3)0.074 (3)−0.004 (2)0.054 (3)−0.010 (2)
C90.087 (4)0.080 (3)0.066 (3)0.013 (3)0.037 (3)−0.004 (2)
C100.100 (4)0.116 (4)0.101 (4)0.011 (4)0.064 (4)−0.021 (4)
C110.071 (3)0.088 (3)0.089 (4)−0.002 (3)0.039 (3)−0.016 (3)
C120.078 (4)0.099 (4)0.089 (4)0.008 (3)0.033 (3)−0.010 (3)
C130.075 (4)0.133 (5)0.091 (4)−0.012 (4)0.042 (4)0.015 (4)
C140.116 (6)0.141 (6)0.084 (4)−0.059 (5)0.052 (4)−0.009 (4)
C150.158 (8)0.116 (5)0.138 (6)−0.047 (6)0.106 (7)−0.041 (5)
C160.108 (5)0.099 (4)0.152 (6)−0.006 (4)0.091 (5)−0.020 (4)
C170.068 (3)0.050 (2)0.078 (3)−0.0074 (19)0.046 (3)−0.0058 (19)
C180.082 (3)0.067 (3)0.101 (4)−0.002 (2)0.056 (3)−0.009 (3)
C190.093 (4)0.059 (3)0.100 (4)−0.008 (2)0.059 (3)−0.006 (2)
C200.087 (4)0.064 (3)0.090 (4)0.001 (2)0.058 (3)0.006 (2)
C210.143 (6)0.133 (5)0.111 (5)0.037 (5)0.084 (5)0.026 (4)
C220.161 (8)0.177 (9)0.109 (6)0.082 (7)0.060 (6)0.045 (5)
C230.084 (5)0.103 (5)0.174 (8)0.030 (4)0.061 (6)0.019 (5)
C240.129 (6)0.121 (6)0.174 (8)0.014 (5)0.109 (6)−0.024 (6)
C250.104 (4)0.086 (3)0.107 (4)0.002 (3)0.075 (4)−0.005 (3)
O10.248 (6)0.096 (3)0.196 (5)0.007 (4)0.190 (5)0.018 (3)
Br10.1042 (4)0.0715 (3)0.0851 (4)−0.0021 (3)0.0595 (3)0.0094 (2)
Geometric parameters (Å, °) top
O1—HW10.84 (7)C23—C241.355 (16)
O1—HW20.84 (11)C24—C251.356 (15)
N1—C11.390 (6)C2—H20.9300
N1—C71.323 (6)C3—H30.9300
N1—C171.480 (5)C4—H40.9300
N2—C61.399 (6)C5—H50.9300
N2—C81.469 (6)C7—H70.9300
N2—C71.313 (5)C8—H8B0.9700
C1—C61.386 (5)C8—H8A0.9700
C1—C21.389 (7)C9—H9B0.9700
C2—C31.365 (7)C9—H9A0.9700
C3—C41.392 (6)C10—H10A0.9700
C4—C51.373 (8)C10—H10B0.9700
C5—C61.376 (6)C12—H120.9300
C8—C91.539 (8)C13—H130.9300
C9—C101.455 (8)C14—H140.9300
C10—C111.511 (10)C15—H150.9300
C11—C121.376 (11)C16—H160.9300
C11—C161.382 (9)C17—H17A0.9700
C12—C131.363 (10)C17—H17B0.9700
C13—C141.327 (12)C18—H18B0.9700
C14—C151.355 (17)C18—H18A0.9700
C15—C161.350 (15)C19—H19B0.9700
C17—C181.535 (9)C19—H19A0.9700
C18—C191.483 (7)C21—H210.9300
C19—C201.514 (10)C22—H220.9300
C20—C251.336 (12)C23—H230.9300
C20—C211.377 (9)C24—H240.9300
C21—C221.384 (16)C25—H250.9300
C22—C231.313 (19)
Br1···O13.318 (8)HW2···Br1iii2.96 (8)
Br1···O1i3.383 (5)HW2···H8Biii2.5800
Br1···HW1i3.04 (9)H3···Br1iv3.2000
Br1···H17Bii3.1100H5···C83.0200
Br1···H8Aiii3.0900H5···C20vi3.0900
Br1···H3iv3.2000H5···H9A2.5900
Br1···HW2i2.96 (8)H7···O12.5000
Br1···H8B3.2200H7···H17A2.5700
Br1···H2ii3.1600H7···H8B2.4800
Br1···H13v3.1000H8A···H10A2.4100
O1···C173.236 (13)H8A···Br1i3.0900
O1···Br1iii3.383 (5)H8A···C53.0600
O1···C73.257 (10)H8B···H10B2.5500
O1···Br13.318 (8)H8B···HW2i2.5800
O1···H17A2.3800H8B···H72.4800
O1···H72.5000H8B···Br13.2200
N1···N22.175 (5)H9A···C52.9900
N2···N12.175 (5)H9A···C122.9600
C1···C6iv3.509 (7)H9A···H52.5900
C2···C8iv3.597 (7)H9A···C62.9700
C3···C7iv3.568 (9)H9B···C13v3.0500
C4···C7iv3.528 (8)H9B···C122.8500
C5···C93.574 (7)H9B···H122.3300
C6···C1iv3.509 (7)H10A···H8A2.4100
C7···O13.257 (10)H10A···H162.3900
C7···C3iv3.568 (9)H10B···H25ii2.4300
C7···C4iv3.528 (8)H10B···H8B2.5500
C8···C2iv3.597 (7)H12···H9B2.3300
C9···C53.574 (7)H12···C25vii3.0700
C17···O13.236 (13)H12···C92.6900
C1···H18B3.0900H13···Br1v3.1000
C2···H17B2.9500H14···HW1v2.3300
C5···H9A2.9900H15···H21v2.5400
C5···H8A3.0600H16···H10A2.3900
C6···H9A2.9700H17A···O12.3800
C7···H18A3.0700H17A···H19A2.5500
C8···H53.0200H17A···H72.5700
C9···H122.6900H17B···C22.9500
C11···H22vi3.0200H17B···H22.5600
C11···H24ii2.9000H17B···Br1x3.1100
C12···H9A2.9600H18A···C212.9400
C12···H9B2.8500H18A···C73.0700
C13···H9Bv3.0500H18B···C13.0900
C15···H24ii3.0600H19A···H17A2.5500
C16···H24ii2.8100H19A···H212.5100
C17···H23.0200H19B···H252.3800
C18···H23vii3.0700H21···H15v2.5400
C20···H5viii3.0900H21···H19A2.5100
C21···H18A2.9400H22···C11viii3.0200
C25···H12ix3.0700H23···C18ix3.0700
HW1···H14v2.3300H24···C11x2.9000
HW1···Br1iii3.04 (9)H24···C16x2.8100
H2···Br1x3.1600H24···C15x3.0600
H2···H17B2.5600H25···H10Bx2.4300
H2···C173.0200H25···H19B2.3800
HW1—O1—HW2105 (9)N2—C8—H8A109.00
C1—N1—C7107.9 (3)C9—C8—H8A109.00
C1—N1—C17126.5 (4)C9—C8—H8B109.00
C7—N1—C17125.6 (4)N2—C8—H8B109.00
C6—N2—C7108.1 (4)H8A—C8—H8B108.00
C6—N2—C8126.3 (4)C8—C9—H9B109.00
C7—N2—C8125.6 (4)C10—C9—H9A109.00
N1—C1—C6106.7 (4)C10—C9—H9B109.00
C2—C1—C6121.8 (4)H9A—C9—H9B108.00
N1—C1—C2131.5 (4)C8—C9—H9A109.00
C1—C2—C3115.9 (4)C9—C10—H10A108.00
C2—C3—C4122.1 (5)C9—C10—H10B108.00
C3—C4—C5122.2 (5)C11—C10—H10B108.00
C4—C5—C6115.9 (4)H10A—C10—H10B107.00
N2—C6—C1106.2 (4)C11—C10—H10A108.00
C1—C6—C5122.1 (4)C11—C12—H12120.00
N2—C6—C5131.8 (4)C13—C12—H12120.00
N1—C7—N2111.2 (5)C12—C13—H13120.00
N2—C8—C9111.1 (5)C14—C13—H13120.00
C8—C9—C10112.5 (6)C15—C14—H14120.00
C9—C10—C11117.0 (7)C13—C14—H14120.00
C10—C11—C12123.8 (6)C16—C15—H15120.00
C12—C11—C16117.7 (7)C14—C15—H15120.00
C10—C11—C16118.5 (8)C11—C16—H16120.00
C11—C12—C13120.6 (6)C15—C16—H16120.00
C12—C13—C14120.2 (9)N1—C17—H17B110.00
C13—C14—C15120.8 (9)C18—C17—H17A110.00
C14—C15—C16120.2 (8)N1—C17—H17A110.00
C11—C16—C15120.5 (9)H17A—C17—H17B108.00
N1—C17—C18108.6 (4)C18—C17—H17B110.00
C17—C18—C19113.8 (5)C17—C18—H18A109.00
C18—C19—C20110.4 (6)C17—C18—H18B109.00
C19—C20—C21120.7 (8)C19—C18—H18B109.00
C19—C20—C25121.4 (6)H18A—C18—H18B108.00
C21—C20—C25117.9 (8)C19—C18—H18A109.00
C20—C21—C22120.0 (10)C18—C19—H19B110.00
C21—C22—C23120.8 (9)C20—C19—H19A110.00
C22—C23—C24118.9 (12)C20—C19—H19B110.00
C23—C24—C25121.2 (12)H19A—C19—H19B108.00
C20—C25—C24120.9 (8)C18—C19—H19A110.00
C3—C2—H2122.00C22—C21—H21120.00
C1—C2—H2122.00C20—C21—H21120.00
C2—C3—H3119.00C21—C22—H22120.00
C4—C3—H3119.00C23—C22—H22120.00
C5—C4—H4119.00C24—C23—H23120.00
C3—C4—H4119.00C22—C23—H23121.00
C4—C5—H5122.00C23—C24—H24119.00
C6—C5—H5122.00C25—C24—H24119.00
N2—C7—H7124.00C20—C25—H25119.00
N1—C7—H7124.00C24—C25—H25120.00
C7—N1—C1—C2178.3 (6)C4—C5—C6—C1−0.6 (8)
C17—N1—C1—C2−3.8 (8)N2—C8—C9—C10−177.5 (5)
C7—N1—C1—C60.2 (5)C8—C9—C10—C11173.4 (5)
C17—N1—C1—C6178.1 (4)C9—C10—C11—C1224.9 (9)
C1—N1—C7—N20.3 (6)C9—C10—C11—C16−157.8 (7)
C17—N1—C7—N2−177.7 (4)C10—C11—C12—C13174.1 (7)
C1—N1—C17—C18−85.3 (5)C12—C11—C16—C153.1 (13)
C7—N1—C17—C1892.3 (7)C16—C11—C12—C13−3.2 (11)
C6—N2—C8—C972.9 (5)C10—C11—C16—C15−174.4 (9)
C7—N2—C8—C9−107.4 (6)C11—C12—C13—C141.0 (12)
C7—N2—C6—C5−177.9 (6)C12—C13—C14—C151.4 (14)
C8—N2—C6—C51.8 (9)C13—C14—C15—C16−1.5 (17)
C7—N2—C6—C10.6 (5)C14—C15—C16—C11−0.8 (16)
C8—N2—C6—C1−179.7 (4)N1—C17—C18—C19−175.7 (5)
C6—N2—C7—N1−0.6 (6)C17—C18—C19—C20−179.6 (5)
C8—N2—C7—N1179.7 (4)C18—C19—C20—C21−81.0 (8)
N1—C1—C2—C3−177.6 (5)C18—C19—C20—C2597.9 (7)
C2—C1—C6—C5−0.1 (8)C19—C20—C21—C22173.4 (7)
N1—C1—C6—C5178.3 (5)C25—C20—C21—C22−5.5 (11)
C6—C1—C2—C30.4 (8)C19—C20—C25—C24−177.4 (7)
C2—C1—C6—N2−178.8 (5)C21—C20—C25—C241.5 (10)
N1—C1—C6—N2−0.5 (5)C20—C21—C22—C234.6 (14)
C1—C2—C3—C40.1 (8)C21—C22—C23—C240.6 (14)
C2—C3—C4—C5−0.9 (9)C22—C23—C24—C25−4.8 (14)
C3—C4—C5—C61.1 (8)C23—C24—C25—C203.8 (13)
C4—C5—C6—N2177.8 (5)
Symmetry codes: (i) −x, y−1/2, −z+3/2; (ii) x, −y+1/2, z−1/2; (iii) −x, y+1/2, −z+3/2; (iv) −x, −y, −z+2; (v) −x−1, −y, −z+1; (vi) x, y−1, z; (vii) −x−1, y−1/2, −z+3/2; (viii) x, y+1, z; (ix) −x−1, y+1/2, −z+3/2; (x) x, −y+1/2, z+1/2.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C7—H7···O10.932.503.257 (10)139
C17—H17A···O10.972.383.236 (13)148
C24—H24···Cg1x0.932.843.771 (14)176
Symmetry codes: (x) x, −y+1/2, z+1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C7—H7···O10.932.503.257 (10)139
C17—H17A···O10.972.383.236 (13)148
C24—H24···Cg1i0.932.843.771 (14)176
Symmetry codes: (i) x, −y+1/2, z+1/2.
Acknowledgements top

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS II diffractometer (purchased under grant F.279 of the University Research Fund). HK and ÜY thank İnönü University Research Fund (Directed project BAPB-2008/60) for financial support ofthis study.

references
References top

Akkurt, M., Karaca, S., Küçükbay, H., Orhan, E. & Büyükgüngör, O. (2005). Acta Cryst. E61, o2452–o2454.

Akkurt, M., Öztürk, S., Küçükbay, H., Orhan, E. & Büyükgüngör, O. (2004). Acta Cryst. E60, o219–o221.

Akkurt, M., Pınar, Ş., Yılmaz, Ü., Küçükbay, H. & Büyükgüngör, O. (2007). Acta Cryst. E63, o379–o381.

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119.

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.

Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.

Karaca, S., Akkurt, M., Yılmaz, U., Küçükbay, H. & Büyükgüngör, O. (2005). Acta Cryst. E61, o2128–o2130.

Küçükbay, H., Durmaz, R., Güven, M. & Günal, S. (2001). Arzneim. Forsch. Drug. Res. 51, 420–424.

Küçükbay, H., Durmaz, R., Okuyucu, N., Günal, S. & Kazaz, C. (2004). Arzneim. Forsch. Drug. Res. 54, 64–68.

Küçükbay, H., Durmaz, H., Orhan, E. & Günal, S. (2003). Farmaco, 58, 431–437.

Pınar, Ş., Akkurt, M., Küçükbay, H., Şireci, N. & Büyükgüngör, O. (2006). Acta Cryst. E62, o2223–o2225.

Sakai, T., Hamada, T., Awata, N. & Watanabe, J. (1989). Pharmacobiol. Dyn. 12, 530–536.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.

Yıldırım, S. O., Akkurt, M., Küçükbay, H., Orhan, E. & Büyükgüngör, O. (2005). Acta Cryst. E61, o2038–o2039.