1-(Prop-2-en-1-yl)-3-[(trimethyl­sil­yl)meth­yl]benzimidazolium bromide monohydrate

Baktır, Z.; Akkurt, M.; Şireci, N.; Küçükbay, H.

doi:10.1107/S1600536810033015

organic compounds

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ISSN: 2056-9890

Volume 66| Part 9| September 2010| Pages o2393-o2394

https://doi.org/10.1107/S1600536810033015

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1-(Prop-2-en-1-yl)-3-[(trimethylsilyl)methyl]benzimidazolium bromide monohydrate

Zeliha Baktır,^a Mehmet Akkurt,^a ^* Nihat Şireci ^b and Hasan Küçükbay ^c

^aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^bDepartment of Chemistry, Faculty of Arts and Sciences, Adıyaman University, 02040 Adıyaman, Turkey, and ^cDepartment of Chemistry, Faculty of Arts and Sciences, Ínönü University, 44280 Malatya, Turkey
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 12 August 2010; accepted 16 August 2010; online 25 August 2010)

In the title compound, C₁₄H₂₁N₂Si⁺·Br⁻·H₂O, the benzimidazole ring system is almost planar [maximum deviation = 0.021 (2) Å]. In the crystal, O—H⋯Br and C—H⋯O hydrogen bonds link the ions via the O atoms of the water molecules. In addition, there are π–π stacking interactions between the centroids of the benzene and imidazole rings of the benzimidazole ring system [centroid–centroid distances = 3.521 (3) and 3.575 (2) Å].

Related literature

For the antitumour activity of alkylsilyl-substituted benzimidazole derivatives, see: Kleemann et al. (2009 ); Lukevics et al. (2001 ); Ignatovich et al. (2010 ). For the pharmacological activity of benzimidazole compounds, see: Singh & Lown (2000 ); Huang et al. (2006 ); Turner & Denny (1996 ); Galal et al. (2009 ); Küçükbay et al. (2003 , 2004 , 2009 , 2010a ,b ); Şireci et al. (2010 ); Yılmaz & Küçükbay (2009 ); Yılmaz et al. (2010 ). For the structures of similar benzimidazole derivatives, see: Akkurt et al. (2008 , 2010a ,b ); Yıldırım et al. (2006 ). For π–π interactions, see: Janiak (2000 ).

Experimental

Crystal data

C₁₄H₂₁N₂Si⁺·Br⁻·H₂O
M_r = 343.33
Triclinic, $[P \overline 1]$
a = 8.9063 (2) Å
b = 10.4720 (2) Å
c = 10.9439 (3) Å
α = 66.542 (4)°
β = 71.479 (4)°
γ = 80.625 (5)°
V = 887.07 (5) Å³
Z = 2
Mo Kα radiation
μ = 2.38 mm⁻¹
T = 294 K
0.20 × 0.20 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID-S diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1995 ) T_min = 0.647, T_max = 0.647
18957 measured reflections
3618 independent reflections
2202 reflections with I > 2σ(I)
R_int = 0.073

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.121
S = 1.02
3618 reflections
175 parameters
3 restraints
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O1W	0.93	2.46	3.351 (5)	161
O1W—H1W⋯Br1	0.85	2.62	3.445 (4)	165
O1W—H2W⋯Br1ⁱ	0.85	2.59	3.360 (4)	152
Symmetry code: (i) -x+2, -y+1, -z+1.

Data collection: CrystalClear (Rigaku/MSC, 2005 ); cell refinement: CrystalClear; data reduction: CrystalClear; 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 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810033015/dn2597sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810033015/dn2597Isup2.hkl

checkCIF report

Comment top

Heterocycles are important building blocks for the construction of anticancer drugs (Kleemann et al., 2009). For example, alkylsilyl substituted benzimidazole derivatives have been reported to possess important antitumour activity (Lukevics et al., 2001; Ignatovich et al., 2010). Since, benzimidazole compounds have been found to have a broad range of pharmacological activity, many research groups as well as our group have been interested in these type of heterocyclic compounds (Singh & Lown, 2000; Huang et al., 2006; Turner & Denny, 1996; Galal et al., 2009; Küçükbay et al., 2003, 2004, 2009, 2010a,b; Şireci et al., 2010; Yılmaz et al., 2009, 2010;). We have synthesized and investigated the crystal structures of many benzimidazole derivatives (Akkurt et al., 2008, 2010a,b; Yıldırım et al., 2006). Herein we report the synthesis and structure of the title compound, (I), 1-(prop-2-ene-1-yl)-3-[(trimethylsilyl)methyl]benzimidazolium bromide monohydrate.

The benzimidazole ring system (N1/N2/C1–C7) in the title molecule (I) (Fig. 1) is almost planar with a maximum deviation of 0.021 (2)Å for C1 atom. The bond lengths and angles in (I) are compatible with those found for similar compounds (Akkurt et al., 2008, 2010a,b). The average Si—C bond length is 1.857 (5) Å. The angles around the Si atoms with a distorted tetrahedral geometry vary from 105.9 (2)° to 111.7 (3)°.

O–H···Br and C—H···O hydrogen bonds link the molecules (Table 1 and Fig 2). In the crystal structure, the benzene (C1–C6) and imidazole (N1/N2/C1/C6/C7) rings of the benzimidazole ring system form π-π stacking interactions with each other (Janiak, 2000) (Table 2).

Related literature top

For the antitumour activity of alkylsilyl-substituted benzimidazole derivatives, see: Kleemann et al. (2009); Lukevics et al. (2001); Ignatovich et al. (2010). For the pharmacological activity of benzimidazole compounds, see: Singh & Lown (2000); Huang et al. (2006); Turner & Denny (1996); Galal et al. (2009); Küçükbay et al. (2003, 2004, 2009, 2010a,b); Şireci et al. (2010); Yılmaz et al. (2009, 2010). For the structures of similar benzimidazole derivatives, see: Akkurt et al. (2008, 2010a,b); Yıldırım et al. (2006). For π–π interactions, see: Janiak (2000).

Experimental top

A mixture of 1-(trimethylsilylmethyl)benzimidazole (1.02 g, 4.99 mmol) and allyl bromide (0.5 ml, 5,78 mmol) in dimethylformamide (5 ml) was refluxed for 3 h. The mixture was then cooled and the volatiles were removed under vacuum. The residue was crystallized from a dimethylformamide/ethanol (1:1). White crystals of the title compound (1.29 g, 79%) were obtained, m.p.: 394–395 °K; υ_(CN)= 1552 cm^-1. Anal. found: C 48.67, H 6.72, N 8.11%. Calculated for C₁₄H₂₃BrN₂OSi: C 48.98, H 6.75, N 8.16%. ¹H NMR (δ, DMSO-d₆): 9.70 (s, 1H, NCHN), 8.14 - 7.67 (m, 4H, C₆H₄), 6.12 (m, 1H, CH allyl), 5.37 (m, 2H, CH₂ allyl), 5.22 (d, 2H, CH₂ allyl, J= 5.7 Hz), 4.26 (s, 2H, CH₂Si) and 0.11 [s, 9H, (CH₃)₃Si]. ¹³C NMR (δ, DMSO-d₆): 141.6 (NCHN), 132.5, 131.9, 131.3, 127.0, 126.8 and 120.4 (C₆H₄), 114.5 (CH allyl), 114.2 (CH₂ allyl), 49.2 (CH₂ allyl), 38.4 (CH₂Si) and -2.2 [(CH₃)₃Si].

Structure description top

For the antitumour activity of alkylsilyl-substituted benzimidazole derivatives, see: Kleemann et al. (2009); Lukevics et al. (2001); Ignatovich et al. (2010). For the pharmacological activity of benzimidazole compounds, see: Singh & Lown (2000); Huang et al. (2006); Turner & Denny (1996); Galal et al. (2009); Küçükbay et al. (2003, 2004, 2009, 2010a,b); Şireci et al. (2010); Yılmaz et al. (2009, 2010). For the structures of similar benzimidazole derivatives, see: Akkurt et al. (2008, 2010a,b); Yıldırım et al. (2006). For π–π interactions, see: Janiak (2000).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); 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) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. View of the title molecule with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii. Hydrogen bonds are shown as dashed lines.
	Fig. 2. Packing view of the title compound with O–H···Br and C—H···O hydrogen bonds viewed down the a axis. H atoms not involved in hydrogen bondings are omitted for the sake of clarity. [Symmetry code: (i) -x+2, -y+1, -z+1]

1-(Prop-2-en-1-yl)-3-[(trimethylsilyl)methyl]benzimidazolium bromide monohydrate top

Crystal data top

C₁₄H₂₁N₂Si⁺·Br⁻·H₂O	Z = 2
M_r = 343.33	F(000) = 356
Triclinic, P1	D_x = 1.285 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.9063 (2) Å	Cell parameters from 3185 reflections
b = 10.4720 (2) Å	θ = 2.4–26.4°
c = 10.9439 (3) Å	µ = 2.38 mm⁻¹
α = 66.542 (4)°	T = 294 K
β = 71.479 (4)°	Block, white
γ = 80.625 (5)°	0.20 × 0.20 × 0.20 mm
V = 887.07 (5) Å³

Data collection top

Rigaku R-AXIS RAPID-S diffractometer	3618 independent reflections
Radiation source: Sealed Tube	2202 reflections with I > 2σ(I)
Graphite Monochromator monochromator	R_int = 0.073
Detector resolution: 10.0000 pixels mm^-1	θ_max = 26.4°, θ_min = 2.4°
dtprofit.ref scans	h = −11→9
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −13→13
T_min = 0.647, T_max = 0.647	l = −13→13
18957 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.121	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0356P)² + 0.3659P] where P = (F_o² + 2F_c²)/3
3618 reflections	(Δ/σ)_max = 0.006
175 parameters	Δρ_max = 0.30 e Å⁻³
3 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₁₄H₂₁N₂Si⁺·Br⁻·H₂O	γ = 80.625 (5)°
M_r = 343.33	V = 887.07 (5) Å³
Triclinic, P1	Z = 2
a = 8.9063 (2) Å	Mo Kα radiation
b = 10.4720 (2) Å	µ = 2.38 mm⁻¹
c = 10.9439 (3) Å	T = 294 K
α = 66.542 (4)°	0.20 × 0.20 × 0.20 mm
β = 71.479 (4)°

Data collection top

Rigaku R-AXIS RAPID-S diffractometer	3618 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	2202 reflections with I > 2σ(I)
T_min = 0.647, T_max = 0.647	R_int = 0.073
18957 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	3 restraints
wR(F²) = 0.121	H-atom parameters constrained
S = 1.02	Δρ_max = 0.30 e Å⁻³
3618 reflections	Δρ_min = −0.35 e Å⁻³
175 parameters

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

	x	y	z	U_iso*/U_eq
Si1	0.53721 (14)	0.18235 (12)	0.70600 (11)	0.0684 (3)
N1	0.6155 (3)	0.3381 (3)	0.8362 (3)	0.0570 (7)
N2	0.7515 (3)	0.3069 (3)	0.9818 (3)	0.0624 (8)
C1	0.5921 (4)	0.3128 (4)	1.0536 (4)	0.0562 (9)
C2	0.5185 (5)	0.3059 (4)	1.1879 (4)	0.0669 (10)
H2	0.5760	0.2927	1.2499	0.080*
C3	0.3555 (5)	0.3197 (4)	1.2249 (4)	0.0722 (11)
H3	0.3016	0.3143	1.3147	0.087*
C4	0.2689 (5)	0.3415 (4)	1.1314 (4)	0.0673 (10)
H4	0.1590	0.3509	1.1604	0.081*
C5	0.3419 (4)	0.3495 (4)	0.9978 (4)	0.0625 (9)
H5	0.2844	0.3649	0.9353	0.075*
C6	0.5059 (4)	0.3332 (4)	0.9609 (3)	0.0546 (8)
C7	0.7597 (4)	0.3221 (4)	0.8533 (4)	0.0634 (10)
H7	0.8535	0.3216	0.7846	0.076*
C8	0.5773 (5)	0.3529 (4)	0.7092 (3)	0.0634 (10)
H8A	0.6649	0.3954	0.6294	0.076*
H8B	0.4847	0.4153	0.7007	0.076*
C9	0.7201 (6)	0.0716 (5)	0.7079 (6)	0.1093 (17)
H9A	0.7050	−0.0136	0.7007	0.164*
H9B	0.7453	0.0508	0.7931	0.164*
H9C	0.8055	0.1197	0.6310	0.164*
C10	0.4835 (6)	0.2278 (6)	0.5440 (5)	0.1070 (17)
H10A	0.3868	0.2840	0.5472	0.160*
H10B	0.4690	0.1442	0.5337	0.160*
H10C	0.5666	0.2790	0.4667	0.160*
C11	0.3721 (6)	0.0963 (5)	0.8586 (5)	0.1049 (16)
H11A	0.3672	0.0022	0.8668	0.157*
H11B	0.2741	0.1463	0.8470	0.157*
H11C	0.3897	0.0958	0.9409	0.157*
C12	0.8871 (5)	0.2883 (5)	1.0387 (4)	0.0781 (12)
H12A	0.8701	0.3488	1.0902	0.094*
H12B	0.9831	0.3152	0.9629	0.094*
C13	0.9078 (5)	0.1417 (5)	1.1316 (6)	0.0889 (14)
H13	0.9301	0.0731	1.0937	0.107*
C14	0.8967 (6)	0.1037 (6)	1.2611 (7)	0.1190 (19)
H14A	0.8744	0.1698	1.3021	0.143*
H14B	0.9109	0.0101	1.3139	0.143*
O1W	1.0389 (5)	0.3039 (4)	0.5704 (4)	0.1283 (12)
H1W	1.0104	0.3435	0.4962	0.192*
H2W	1.0969	0.3573	0.5761	0.192*
Br1	0.85464 (5)	0.48204 (5)	0.31301 (5)	0.0895 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Si1	0.0770 (8)	0.0756 (7)	0.0588 (6)	−0.0017 (6)	−0.0259 (6)	−0.0264 (6)
N1	0.0539 (18)	0.067 (2)	0.0517 (17)	−0.0005 (14)	−0.0141 (14)	−0.0253 (15)
N2	0.0522 (18)	0.076 (2)	0.065 (2)	−0.0021 (15)	−0.0165 (15)	−0.0321 (17)
C1	0.052 (2)	0.064 (2)	0.055 (2)	−0.0033 (17)	−0.0155 (17)	−0.0241 (18)
C2	0.071 (3)	0.080 (3)	0.055 (2)	−0.005 (2)	−0.018 (2)	−0.029 (2)
C3	0.072 (3)	0.082 (3)	0.059 (2)	−0.007 (2)	−0.005 (2)	−0.030 (2)
C4	0.054 (2)	0.073 (3)	0.072 (3)	−0.0029 (19)	−0.008 (2)	−0.031 (2)
C5	0.055 (2)	0.066 (2)	0.066 (2)	0.0009 (18)	−0.0174 (19)	−0.0259 (19)
C6	0.052 (2)	0.061 (2)	0.053 (2)	−0.0012 (16)	−0.0122 (17)	−0.0258 (17)
C7	0.053 (2)	0.076 (3)	0.062 (2)	−0.0019 (18)	−0.0085 (18)	−0.032 (2)
C8	0.069 (2)	0.072 (3)	0.045 (2)	−0.0009 (19)	−0.0158 (18)	−0.0188 (18)
C9	0.107 (4)	0.087 (3)	0.137 (5)	0.015 (3)	−0.043 (3)	−0.044 (3)
C10	0.121 (4)	0.144 (5)	0.079 (3)	−0.010 (3)	−0.041 (3)	−0.053 (3)
C11	0.120 (4)	0.103 (4)	0.090 (3)	−0.039 (3)	−0.011 (3)	−0.035 (3)
C12	0.056 (2)	0.107 (4)	0.085 (3)	−0.005 (2)	−0.027 (2)	−0.042 (3)
C13	0.067 (3)	0.099 (4)	0.115 (4)	0.009 (2)	−0.044 (3)	−0.044 (3)
C14	0.098 (4)	0.117 (5)	0.130 (5)	0.009 (3)	−0.055 (4)	−0.022 (4)
O1W	0.124 (3)	0.130 (3)	0.132 (3)	−0.002 (2)	−0.047 (2)	−0.042 (2)
Br1	0.0699 (3)	0.1215 (4)	0.0769 (3)	0.0007 (3)	−0.0195 (2)	−0.0391 (3)

Geometric parameters (Å, º) top

Si1—C9	1.840 (5)	C8—H8A	0.9700
Si1—C10	1.842 (4)	C8—H8B	0.9700
Si1—C11	1.854 (5)	C9—H9A	0.9600
Si1—C8	1.893 (4)	C9—H9B	0.9600
N1—C7	1.329 (4)	C9—H9C	0.9600
N1—C6	1.390 (4)	C10—H10A	0.9600
N1—C8	1.478 (4)	C10—H10B	0.9600
N2—C7	1.330 (4)	C10—H10C	0.9600
N2—C1	1.392 (4)	C11—H11A	0.9600
N2—C12	1.480 (5)	C11—H11B	0.9600
C1—C2	1.383 (5)	C11—H11C	0.9600
C1—C6	1.390 (5)	C12—C13	1.486 (6)
C2—C3	1.377 (5)	C12—H12A	0.9700
C2—H2	0.9300	C12—H12B	0.9700
C3—C4	1.397 (5)	C13—C14	1.285 (7)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.372 (5)	C14—H14A	0.9300
C4—H4	0.9300	C14—H14B	0.9300
C5—C6	1.387 (5)	O1W—H1W	0.8512
C5—H5	0.9300	O1W—H2W	0.8513
C7—H7	0.9300

C9—Si1—C10	111.7 (2)	Si1—C8—H8A	108.8
C9—Si1—C11	110.6 (2)	N1—C8—H8B	108.8
C10—Si1—C11	110.6 (2)	Si1—C8—H8B	108.8
C9—Si1—C8	107.8 (2)	H8A—C8—H8B	107.7
C10—Si1—C8	105.9 (2)	Si1—C9—H9A	109.5
C11—Si1—C8	110.15 (19)	Si1—C9—H9B	109.5
C7—N1—C6	108.0 (3)	H9A—C9—H9B	109.5
C7—N1—C8	126.3 (3)	Si1—C9—H9C	109.5
C6—N1—C8	125.7 (3)	H9A—C9—H9C	109.5
C7—N2—C1	107.9 (3)	H9B—C9—H9C	109.5
C7—N2—C12	126.3 (3)	Si1—C10—H10A	109.5
C1—N2—C12	125.8 (3)	Si1—C10—H10B	109.5
C2—C1—C6	121.7 (3)	H10A—C10—H10B	109.5
C2—C1—N2	131.6 (3)	Si1—C10—H10C	109.5
C6—C1—N2	106.7 (3)	H10A—C10—H10C	109.5
C3—C2—C1	116.5 (3)	H10B—C10—H10C	109.5
C3—C2—H2	121.8	Si1—C11—H11A	109.5
C1—C2—H2	121.8	Si1—C11—H11B	109.5
C2—C3—C4	121.9 (4)	H11A—C11—H11B	109.5
C2—C3—H3	119.0	Si1—C11—H11C	109.5
C4—C3—H3	119.0	H11A—C11—H11C	109.5
C5—C4—C3	121.7 (4)	H11B—C11—H11C	109.5
C5—C4—H4	119.2	N2—C12—C13	111.7 (3)
C3—C4—H4	119.2	N2—C12—H12A	109.3
C4—C5—C6	116.6 (3)	C13—C12—H12A	109.3
C4—C5—H5	121.7	N2—C12—H12B	109.3
C6—C5—H5	121.7	C13—C12—H12B	109.3
C5—C6—N1	131.6 (3)	H12A—C12—H12B	107.9
C5—C6—C1	121.7 (3)	C14—C13—C12	124.1 (5)
N1—C6—C1	106.7 (3)	C14—C13—H13	118.0
N2—C7—N1	110.8 (3)	C12—C13—H13	118.0
N2—C7—H7	124.6	C13—C14—H14A	120.0
N1—C7—H7	124.6	C13—C14—H14B	120.0
N1—C8—Si1	113.9 (2)	H14A—C14—H14B	120.0
N1—C8—H8A	108.8	H1W—O1W—H2W	109.9

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1W	0.93	2.46	3.351 (5)	161
O1W—H1W···Br1	0.85	2.62	3.445 (4)	165
O1W—H2W···Br1ⁱ	0.85	2.59	3.360 (4)	152

Symmetry code: (i) −x+2, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₄H₂₁N₂Si⁺·Br⁻·H₂O
M_r	343.33
Crystal system, space group	Triclinic, P1
Temperature (K)	294
a, b, c (Å)	8.9063 (2), 10.4720 (2), 10.9439 (3)
α, β, γ (°)	66.542 (4), 71.479 (4), 80.625 (5)
V (Å³)	887.07 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.38
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Rigaku R-AXIS RAPID-S
Absorption correction	Multi-scan (SORTAV; Blessing, 1995)
T_min, T_max	0.647, 0.647
No. of measured, independent and observed [I > 2σ(I)] reflections	18957, 3618, 2202
R_int	0.073
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.121, 1.02
No. of reflections	3618
No. of parameters	175
No. of restraints	3
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.35

Computer programs: CrystalClear (Rigaku/MSC, 2005), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1W	0.93	2.46	3.351 (5)	160.8
O1W—H1W···Br1	0.85	2.62	3.445 (4)	164.7
O1W—H2W···Br1ⁱ	0.85	2.59	3.360 (4)	151.7

Symmetry code: (i) −x+2, −y+1, −z+1.

π-π contacts (Å, °) top

Cg1: N1,N2,C1,C6,C7; Cg2: C1,C2,C3,C4,C5,C6; ccd: Distance between ring centroids; ipd: mean interplanar distance (Distance from one plane to the neighbouring centroid); sa: mean slippage angle (Angle subtended by the intercentroid vector to the plane normal). For details, see Janiak (2000).

ring 1/ring 2	ccd	ipd	sa
Cg1->Cg2ⁱⁱ	3.521 (3)	3.386	15.9
Cg2->Cg2ⁱⁱ	3.575 (2)	3.396	18.2

Symmetry code: (ii) 1-x,1-y,2-z.

Acknowledgements

ZB and MA thank the Unit of the Scientific Research Projects of Erciyes University, Turkey for the research grant FBD-10–2949, and for support of the data collection at Atatürk University, Turkey. HK and NŞ thank İnönü University Research Fund (BAPB-2008–60) for financial support of this study.

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