1,3-Difurfurylbenzimidazolium chloride monohydrate

Akkurt, M.; Şireci, N.; Deniz, S.; Küçükbay, H.; Büyükgüngör, O.

doi:10.1107/S1600536809029626

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Pages o2037-o2038

doi:10.1107/S1600536809029626

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1,3-Difurfurylbenzimidazolium chloride monohydrate

Mehmet Akkurt,^a ^* Nihat Şireci,^b Selma Deniz,^c Hasan Küçükbay ^c and Orhan Büyükgüngör ^d

^aDepartment of Physics, Faculty of Arts and Sciences, Erciyes University, 38039 Kayseri, Turkey, ^bDepartment of Chemistry, Faculty of Arts and Sciences, Adıyaman University, 02040 Adıyaman, Turkey, ^cDepartment of Chemistry, Faculty of Arts and Sciences, nönü University, 44280 Malatya, Turkey, and ^dDepartment of Physics, Faculty of Arts & Science, Ondokuz Mayıs University, 55139 Kurupelit-Samsun, Turkey
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 24 July 2009; accepted 24 July 2009; online 29 July 2009)

The title compound, C₁₇H₁₅N₂O₂⁺·Cl⁻·H₂O, was synthesized from benzimidazole and furfryl chloride in dimethylformamide. The cationic benzimidazolium ring is connected to two furan rings via methylene bridges. The furan rings make dihedral angle of 79.09 (18)° with respect to each other, and make dihedral angles of 73.92 (12) and 72.58 (13)° with respect to the benzimidazole ring. O—H⋯Cl, C—H⋯O and C—H⋯Cl hydrogen bonds and C—H⋯π interactions contribute to the stabilization of the crystal structure. Furthermore, there is a π–π interaction between adjacent five- and six-membered rings of the benzimidazole groups [centroid–centroid distance = 3.5305 (8) Å].

Related literature

For the biological activity of furan derivatives, see: Ji et al. (2009 ). For the antimicrobial activity of a large number of organic and organometallic derivatives of benzimidazole against standard bacterial strains, see: Küçükbay & Durmaz (1997 ); Küçükbay et al. (2001 , 2004 , 2009 ); Çetinkaya et al. (1996 ). For the catalytic activity of furans, see: Küçükbay et al. (1996 ). For related structures, see: Yıldırım et al. (2007 ); Akkurt et al. (2006 , 2007 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₇H₁₅N₂O₂⁺·Cl⁻·H₂O
M_r = 332.78
Triclinic, $[P \overline 1]$
a = 9.0201 (5) Å
b = 9.3135 (5) Å
c = 11.2711 (6) Å
α = 66.778 (4)°
β = 81.869 (4)°
γ = 73.656 (4)°
V = 834.50 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 296 K
0.58 × 0.49 × 0.38 mm

Data collection

Stoe IPDS II diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ) T_min = 0.871, T_max = 0.913
15618 measured reflections
3780 independent reflections
2972 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.122
S = 1.04
3780 reflections
214 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—HW1⋯Cl1ⁱ	0.93 (3)	2.27 (3)	3.1563 (17)	159 (3)
O3—HW2⋯Cl1	0.98 (3)	2.22 (3)	3.1848 (17)	168 (3)
C7—H7⋯O3	0.93	2.22	3.133 (2)	168
C8—H8A⋯Cl1ⁱⁱ	0.97	2.75	3.7098 (18)	169
C8—H8B⋯Cl1	0.97	2.67	3.6371 (18)	173
C13—H13A⋯Cl1ⁱ	0.97	2.67	3.6332 (18)	171
C13—H13B⋯Cl1ⁱⁱⁱ	0.97	2.66	3.6290 (19)	177
C11—H11⋯Cg2^iv	0.93	2.85	3.641 (4)	144
C12—H12⋯Cg4^iv	0.93	2.96	3.718 (2)	139
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x, -y, -z+1; (iii) x, y+1, z; (iv) -x, -y, -z+2. Cg2 and Cg4 are the centroids of the O2/C14–C17 furan and C1–C6 benzene rings, respectively.

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; 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 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809029626/xu2569sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809029626/xu2569Isup2.hkl

checkCIF report

Comment top

Like benzimidazoles, furan derivatives occur widely as key structural subunits in numerous natural products, which exhibit interesting biological activities and also in substances of relevance for industry (Ji et al., 2009). Previously, a large number of organic and organometallic derivatives of benzimidazole were prepared in our research laboratory for their antimicrobial activities against standard bacterial strains (Küçükbay & Durmaz, 1997; Küçükbay et al., 2001; Küçükbay et al., 2004; Çetinkaya et al., 1996; Küçükbay et al., 2009) and catalytic activities in some carbon-carbon bond formation reactions and catalytic synthesis of furans (Küçükbay et al., 1996). In connection with these studies, we planned to synthesize having furfuryl substituted new benzimidazole compound (I) and elucidate its crystal structure.

In the asymmetric unit of the title compound (Fig. 1), there are one Cl^- anion, a 1,3-di(furfuryl)benzimidazolium cation and one water molecule. The bond lengths are comparable with those found in earlier work on similar compounds (Allen et al., 1987). The O1/C9–C12 and O2/C14–C17 furan rings and N1/N2/C1–C7 benzimidazole ring are almost planar, with maximum deviations of 0.011 (2) for O1 atoms and -0.013 (2) for O2 atom, and -0.008 (1) Å for N1 atom, respectively. The furan rings make dihedral angles of 79.09 (18)° with each other and 73.92 (12) and 72.58 (13)°, respectively, with the benzimidazole ring.

In the crystal structure of (I), there are O—H···Cl, C—H···O and C—H···Cl hydrogen-bonds (Fig. 2) and C—H···π interactions to stabilize the structure (Table 1). Furthermore, there are π–π interactions between the sequential five- and six membered rings {Cg2 (ring N1/N2/C1/C6/C7)···Cg4 (ring C1–C6) [-x, 1 - x, 1 - z] = 3.5305 (8) Å} of the benzimidazole groups.

Related literature top

For the biological activity of furan derivatives, see: Ji et al. (2009). For the antimicrobial activities of a large number of organic and organometallic derivatives of benzimidazole against standard bacterial strains, see: Küçükbay & Durmaz (1997); Küçükbay et al. (2001, 2004, 2009); Çetinkaya et al. (1996). For catalytic activity in some carbon–carbon bond formation reactions and the catalytic synthesis of furans, see: Küçükbay et al. (1996). For our previous studies of related structures, see: Yıldırım et al. (2007); Akkurt et al. (2006, 2007). For bond-length data, see: Allen et al. (1987). Cg2 and Cg4 are centroids of the O2/C14–C17 furan and C1–C6 benzene rings, respectively.

Experimental top

A mixture of benzimidazole (1.18 g, 10 mmol) and furfuryl chloride (2.3 g, 20 mmol) in DMF (4 ml) was heated under reflux for 4 h. The solution was allowed to cool to room temperature and Et₂O (5 ml) was added. The precipitate was then crystallized from EtOH / Et₂O(2:1). Yield: 1.43 g, 71%, m.p. 488–489 K. ¹HNMR (DMSO-d₆): δ 5.93(4H, s), 6.51(2H, d), 6.84(2H, d),8.12(2H, d), 7.71 (4H, m), 10.21(1H, s). ¹³CNMR (DMSO-d₆): δ 43.05, 111.00, 111.39, 113.99, 126.93, 130.79, 142.37, 144.38, 146.77. Analysis calculated for C₁₇H₁₇N₂O₃Cl: C 61.35, H 5.11, N 8.42%. Found: C 60.97, H 5.06, N 8.38%.

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) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme and 30% probability displacement ellipsoids.
	Fig. 2. View of the hydrogen bonding of (I) in the unit cell.

1,3-Difurfurylbenzimidazolium chloride monohydrate top

Crystal data top

C₁₇H₁₅N₂O₂⁺.Cl⁻·H₂O	Z = 2
M_r = 332.78	F(000) = 348
Triclinic, P1	D_x = 1.324 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.0201 (5) Å	Cell parameters from 20002 reflections
b = 9.3135 (5) Å	θ = 2.0–28.0°
c = 11.2711 (6) Å	µ = 0.25 mm⁻¹
α = 66.778 (4)°	T = 296 K
β = 81.869 (4)°	Prism, colourless
γ = 73.656 (4)°	0.58 × 0.49 × 0.38 mm
V = 834.50 (8) Å³

Data collection top

Stoe IPDS II diffractometer	3780 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	2972 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.024
Detector resolution: 6.67 pixels mm^-1	θ_max = 27.5°, θ_min = 2.0°
ω scans	h = −11→11
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −12→12
T_min = 0.871, T_max = 0.913	l = −14→14
15618 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0718P)² + 0.0531P] where P = (F_o² + 2F_c²)/3
3780 reflections	(Δ/σ)_max < 0.001
214 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₇H₁₅N₂O₂⁺.Cl⁻·H₂O	γ = 73.656 (4)°
M_r = 332.78	V = 834.50 (8) Å³
Triclinic, P1	Z = 2
a = 9.0201 (5) Å	Mo Kα radiation
b = 9.3135 (5) Å	µ = 0.25 mm⁻¹
c = 11.2711 (6) Å	T = 296 K
α = 66.778 (4)°	0.58 × 0.49 × 0.38 mm
β = 81.869 (4)°

Data collection top

Stoe IPDS II diffractometer	3780 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	2972 reflections with I > 2σ(I)
T_min = 0.871, T_max = 0.913	R_int = 0.024
15618 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.27 e Å⁻³
3780 reflections	Δρ_min = −0.21 e Å⁻³
214 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
O1	0.13050 (17)	−0.1335 (2)	0.86538 (14)	0.1035 (5)
O2	0.4854 (2)	0.20834 (19)	0.87489 (17)	0.1120 (7)
N1	0.23659 (12)	0.34379 (14)	0.66557 (10)	0.0532 (3)
N2	0.09145 (13)	0.19641 (13)	0.65802 (11)	0.0538 (3)
C1	0.08420 (14)	0.43162 (16)	0.66979 (12)	0.0494 (4)
C2	0.02240 (17)	0.58200 (18)	0.67695 (15)	0.0603 (4)
C3	−0.13677 (18)	0.63291 (19)	0.67798 (17)	0.0681 (5)
C4	−0.22951 (17)	0.5392 (2)	0.67213 (16)	0.0676 (5)
C5	−0.16859 (16)	0.38960 (19)	0.66484 (14)	0.0590 (4)
C6	−0.00818 (15)	0.33787 (16)	0.66462 (12)	0.0497 (4)
C7	0.23474 (16)	0.20505 (17)	0.65930 (13)	0.0558 (4)
C8	0.04576 (19)	0.05737 (18)	0.65596 (15)	0.0624 (5)
C9	0.0118 (2)	−0.05143 (19)	0.78656 (15)	0.0644 (5)
C10	−0.1182 (3)	−0.0852 (3)	0.8477 (2)	0.0975 (8)
C11	−0.0776 (4)	−0.1983 (4)	0.9725 (3)	0.1193 (11)
C12	0.0683 (4)	−0.2261 (3)	0.9797 (2)	0.1176 (10)
C13	0.37621 (16)	0.3936 (2)	0.67077 (15)	0.0617 (4)
C14	0.41286 (17)	0.3570 (2)	0.80414 (16)	0.0650 (5)
C15	0.3759 (3)	0.4445 (3)	0.8759 (2)	0.1043 (9)
C16	0.4334 (4)	0.3444 (4)	1.0001 (2)	0.1183 (13)
C17	0.4990 (4)	0.2065 (4)	0.9964 (2)	0.1177 (11)
O3	0.50690 (18)	−0.09917 (19)	0.68142 (14)	0.0861 (5)
Cl1	0.33115 (5)	−0.17640 (6)	0.49633 (5)	0.0794 (2)
H2	0.08430	0.64470	0.68080	0.0720*
H3	−0.18370	0.73320	0.68270	0.0820*
H4	−0.33630	0.57900	0.67320	0.0810*
H5	−0.23060	0.32740	0.66040	0.0710*
H7	0.32240	0.12480	0.65620	0.0670*
H8A	−0.04510	0.09600	0.60450	0.0750*
H8B	0.12860	−0.00190	0.61540	0.0750*
H10	−0.21680	−0.04260	0.81460	0.1170*
H11	−0.14480	−0.24430	1.03780	0.1430*
H12	0.12490	−0.29850	1.05160	0.1410*
H13A	0.46300	0.33850	0.63050	0.0740*
H13B	0.36030	0.50870	0.62220	0.0740*
H15	0.32200	0.55240	0.84990	0.1250*
H16	0.42470	0.37400	1.07100	0.1420*
H17	0.54860	0.11780	1.06480	0.1410*
HW1	0.575 (3)	−0.041 (3)	0.627 (3)	0.1190*
HW2	0.461 (3)	−0.139 (3)	0.631 (3)	0.1190*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0817 (9)	0.1176 (11)	0.0752 (8)	−0.0088 (8)	−0.0101 (7)	−0.0070 (8)
O2	0.1417 (15)	0.0792 (9)	0.1012 (11)	−0.0119 (9)	−0.0444 (10)	−0.0164 (8)
N1	0.0444 (5)	0.0560 (6)	0.0524 (6)	−0.0049 (4)	−0.0014 (4)	−0.0183 (5)
N2	0.0547 (6)	0.0514 (6)	0.0531 (6)	−0.0036 (5)	−0.0051 (4)	−0.0227 (5)
C1	0.0449 (6)	0.0519 (7)	0.0450 (6)	−0.0053 (5)	−0.0021 (5)	−0.0159 (5)
C2	0.0582 (8)	0.0536 (7)	0.0680 (8)	−0.0090 (6)	−0.0023 (6)	−0.0250 (6)
C3	0.0610 (8)	0.0584 (8)	0.0812 (10)	0.0015 (7)	−0.0019 (7)	−0.0335 (7)
C4	0.0483 (7)	0.0708 (10)	0.0785 (10)	0.0008 (7)	−0.0030 (7)	−0.0330 (8)
C5	0.0484 (7)	0.0665 (8)	0.0624 (8)	−0.0092 (6)	−0.0047 (6)	−0.0268 (7)
C6	0.0499 (6)	0.0504 (7)	0.0443 (6)	−0.0042 (5)	−0.0039 (5)	−0.0178 (5)
C7	0.0515 (7)	0.0553 (7)	0.0529 (7)	0.0004 (5)	−0.0030 (5)	−0.0212 (6)
C8	0.0729 (9)	0.0566 (8)	0.0621 (8)	−0.0081 (6)	−0.0080 (7)	−0.0302 (6)
C9	0.0726 (9)	0.0580 (8)	0.0649 (8)	−0.0120 (7)	−0.0069 (7)	−0.0267 (7)
C10	0.0818 (13)	0.1172 (17)	0.0885 (13)	−0.0348 (12)	−0.0027 (10)	−0.0263 (12)
C11	0.124 (2)	0.137 (2)	0.0860 (15)	−0.0649 (18)	0.0070 (14)	−0.0115 (14)
C12	0.130 (2)	0.1138 (18)	0.0697 (13)	−0.0187 (16)	−0.0097 (13)	0.0007 (12)
C13	0.0451 (6)	0.0682 (9)	0.0636 (8)	−0.0135 (6)	0.0039 (6)	−0.0184 (7)
C14	0.0531 (7)	0.0719 (9)	0.0681 (9)	−0.0224 (7)	−0.0034 (6)	−0.0190 (7)
C15	0.1222 (18)	0.1028 (16)	0.0819 (13)	0.0002 (13)	−0.0143 (12)	−0.0438 (12)
C16	0.150 (2)	0.147 (3)	0.0756 (13)	−0.062 (2)	−0.0139 (14)	−0.0395 (15)
C17	0.147 (2)	0.114 (2)	0.0847 (15)	−0.0519 (18)	−0.0473 (15)	−0.0017 (14)
O3	0.0829 (8)	0.0841 (9)	0.0778 (8)	−0.0003 (6)	−0.0117 (6)	−0.0271 (7)
Cl1	0.0681 (3)	0.0830 (3)	0.1058 (4)	−0.0237 (2)	0.0067 (2)	−0.0545 (3)

Geometric parameters (Å, º) top

O1—C9	1.339 (2)	C11—C12	1.276 (5)
O1—C12	1.382 (3)	C13—C14	1.469 (2)
O2—C14	1.322 (3)	C14—C15	1.312 (3)
O2—C17	1.385 (3)	C15—C16	1.415 (3)
O3—HW1	0.93 (3)	C16—C17	1.268 (5)
O3—HW2	0.98 (3)	C2—H2	0.9300
N1—C1	1.3929 (19)	C3—H3	0.9300
N1—C7	1.326 (2)	C4—H4	0.9300
N1—C13	1.475 (2)	C5—H5	0.9300
N2—C6	1.393 (2)	C7—H7	0.9300
N2—C8	1.475 (2)	C8—H8A	0.9700
N2—C7	1.320 (2)	C8—H8B	0.9700
C1—C2	1.384 (2)	C10—H10	0.9300
C1—C6	1.387 (2)	C11—H11	0.9300
C2—C3	1.379 (2)	C12—H12	0.9300
C3—C4	1.392 (2)	C13—H13B	0.9700
C4—C5	1.377 (3)	C13—H13A	0.9700
C5—C6	1.390 (2)	C15—H15	0.9300
C8—C9	1.469 (2)	C16—H16	0.9300
C9—C10	1.326 (3)	C17—H17	0.9300
C10—C11	1.408 (4)

Cl1···C8	3.6371 (18)	C5···H8A	2.9500
Cl1···C13ⁱ	3.6290 (19)	C8···H5	3.0100
Cl1···O3ⁱⁱ	3.1563 (17)	C13···H2	3.0100
Cl1···O3	3.1848 (17)	C14···H11^ix	2.9800
Cl1···C13ⁱⁱ	3.6332 (18)	C15···H16^viii	3.0400
Cl1···H13Aⁱⁱ	2.6700	C15···H11^ix	2.9900
Cl1···H8B	2.6700	C16···H16^viii	3.0200
Cl1···H13Bⁱ	2.6600	HW1···Cl1ⁱⁱ	2.27 (3)
Cl1···H8Aⁱⁱⁱ	2.7500	HW1···H3^v	2.5100
Cl1···HW2	2.22 (3)	HW1···H7	2.4300
Cl1···H5ⁱⁱⁱ	3.0100	H2···C13	3.0100
Cl1···HW1ⁱⁱ	2.27 (3)	H2···H13B	2.5800
O1···N2	2.998 (2)	HW2···Cl1	2.22 (3)
O1···C7	3.391 (2)	HW2···H7	2.5300
O2···N1	3.123 (2)	H3···O3^x	2.7900
O3···C17^iv	3.362 (3)	H3···HW1^x	2.5100
O3···Cl1	3.1848 (17)	H5···H8A	2.5700
O3···C7	3.133 (2)	H5···Cl1ⁱⁱⁱ	3.0100
O3···Cl1ⁱⁱ	3.1563 (17)	H5···C8	3.0100
O3···H3^v	2.7900	H7···O3	2.2200
O3···H7	2.2200	H7···HW1	2.4300
O3···H17^iv	2.7800	H7···H8B	2.5400
N1···N2	2.1772 (17)	H7···H13A	2.5500
N1···O2	3.123 (2)	H7···HW2	2.5300
N2···O1	2.998 (2)	H8A···C5	2.9500
N2···N1	2.1772 (17)	H8A···H5	2.5700
C1···C6^vi	3.5787 (18)	H8A···Cl1ⁱⁱⁱ	2.7500
C1···C5^vi	3.5392 (19)	H8B···Cl1	2.6700
C4···C7^vi	3.550 (2)	H8B···H7	2.5400
C5···C1^vi	3.5392 (19)	H11···C14^ix	2.9800
C6···C1^vi	3.5787 (18)	H11···C15^ix	2.9900
C7···O3	3.133 (2)	H12···C5^ix	3.0200
C7···O1	3.391 (2)	H13A···H7	2.5500
C7···C4^vi	3.550 (2)	H13A···Cl1ⁱⁱ	2.6700
C8···Cl1	3.6371 (18)	H13B···C2	2.9600
C13···Cl1ⁱⁱ	3.6332 (18)	H13B···H2	2.5800
C13···Cl1^vii	3.6290 (19)	H13B···Cl1^vii	2.6600
C16···C16^viii	3.435 (5)	H16···C15^viii	3.0400
C17···O3^iv	3.362 (3)	H16···C16^viii	3.0200
C2···H13B	2.9600	H17···O3^iv	2.7800
C5···H12^ix	3.0200

C9—O1—C12	105.62 (19)	O2—C17—C16	109.6 (2)
C14—O2—C17	106.9 (2)	C1—C2—H2	122.00
HW1—O3—HW2	108 (3)	C3—C2—H2	122.00
C1—N1—C13	126.21 (13)	C4—C3—H3	119.00
C7—N1—C13	125.65 (13)	C2—C3—H3	119.00
C1—N1—C7	108.13 (12)	C5—C4—H4	119.00
C6—N2—C8	126.23 (13)	C3—C4—H4	119.00
C7—N2—C8	125.52 (13)	C4—C5—H5	122.00
C6—N2—C7	108.19 (13)	C6—C5—H5	122.00
N1—C1—C2	131.54 (13)	N1—C7—H7	125.00
C2—C1—C6	122.08 (13)	N2—C7—H7	125.00
N1—C1—C6	106.38 (13)	N2—C8—H8B	109.00
C1—C2—C3	115.74 (15)	C9—C8—H8A	109.00
C2—C3—C4	122.20 (17)	C9—C8—H8B	109.00
C3—C4—C5	122.28 (16)	H8A—C8—H8B	108.00
C4—C5—C6	115.51 (15)	N2—C8—H8A	109.00
N2—C6—C1	106.58 (12)	C9—C10—H10	127.00
C1—C6—C5	122.18 (14)	C11—C10—H10	127.00
N2—C6—C5	131.24 (14)	C12—C11—H11	126.00
N1—C7—N2	110.72 (13)	C10—C11—H11	126.00
N2—C8—C9	111.85 (13)	C11—C12—H12	125.00
O1—C9—C10	109.98 (16)	O1—C12—H12	125.00
C8—C9—C10	132.75 (18)	N1—C13—H13A	109.00
O1—C9—C8	117.25 (16)	C14—C13—H13A	109.00
C9—C10—C11	106.4 (2)	C14—C13—H13B	109.00
C10—C11—C12	107.5 (3)	N1—C13—H13B	109.00
O1—C12—C11	110.4 (2)	H13A—C13—H13B	108.00
N1—C13—C14	111.84 (13)	C16—C15—H15	126.00
O2—C14—C15	109.18 (18)	C14—C15—H15	126.00
C13—C14—C15	131.51 (19)	C15—C16—H16	127.00
O2—C14—C13	119.08 (17)	C17—C16—H16	126.00
C14—C15—C16	107.3 (2)	O2—C17—H17	125.00
C15—C16—C17	107.0 (2)	C16—C17—H17	125.00

C12—O1—C9—C10	1.9 (3)	N1—C1—C6—N2	0.25 (14)
C9—O1—C12—C11	−2.1 (3)	N1—C1—C6—C5	−178.98 (12)
C12—O1—C9—C8	−179.56 (18)	N1—C1—C2—C3	179.33 (14)
C17—O2—C14—C15	−2.5 (3)	C2—C1—C6—C5	0.7 (2)
C17—O2—C14—C13	−177.5 (2)	C6—C1—C2—C3	−0.3 (2)
C14—O2—C17—C16	2.3 (4)	C1—C2—C3—C4	0.0 (2)
C13—N1—C1—C6	−178.92 (12)	C2—C3—C4—C5	−0.1 (3)
C7—N1—C13—C14	−95.10 (18)	C3—C4—C5—C6	0.4 (2)
C13—N1—C1—C2	1.4 (2)	C4—C5—C6—N2	−179.78 (14)
C13—N1—C7—N2	178.99 (12)	C4—C5—C6—C1	−0.8 (2)
C1—N1—C13—C14	83.09 (18)	N2—C8—C9—C10	110.2 (3)
C7—N1—C1—C6	−0.47 (14)	N2—C8—C9—O1	−67.9 (2)
C1—N1—C7—N2	0.53 (15)	C8—C9—C10—C11	−179.3 (2)
C7—N1—C1—C2	179.86 (15)	O1—C9—C10—C11	−1.1 (3)
C7—N2—C8—C9	94.03 (18)	C9—C10—C11—C12	−0.2 (4)
C7—N2—C6—C1	0.06 (15)	C10—C11—C12—O1	1.4 (4)
C7—N2—C6—C5	179.19 (14)	N1—C13—C14—O2	80.2 (2)
C6—N2—C7—N1	−0.37 (15)	N1—C13—C14—C15	−93.5 (3)
C8—N2—C6—C1	177.49 (12)	O2—C14—C15—C16	1.7 (3)
C6—N2—C8—C9	−82.98 (18)	C13—C14—C15—C16	176.0 (2)
C8—N2—C7—N1	−177.83 (12)	C14—C15—C16—C17	−0.3 (4)
C8—N2—C6—C5	−3.4 (2)	C15—C16—C17—O2	−1.2 (4)
C2—C1—C6—N2	179.96 (13)

Symmetry codes: (i) x, y−1, z; (ii) −x+1, −y, −z+1; (iii) −x, −y, −z+1; (iv) −x+1, −y, −z+2; (v) x+1, y−1, z; (vi) −x, −y+1, −z+1; (vii) x, y+1, z; (viii) −x+1, −y+1, −z+2; (ix) −x, −y, −z+2; (x) x−1, y+1, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—HW1···Cl1ⁱⁱ	0.93 (3)	2.27 (3)	3.1563 (17)	159 (3)
O3—HW2···Cl1	0.98 (3)	2.22 (3)	3.1848 (17)	168 (3)
C7—H7···O3	0.93	2.22	3.133 (2)	168
C8—H8A···Cl1ⁱⁱⁱ	0.97	2.75	3.7098 (18)	169
C8—H8B···Cl1	0.97	2.67	3.6371 (18)	173
C13—H13A···Cl1ⁱⁱ	0.97	2.67	3.6332 (18)	171
C13—H13B···Cl1^vii	0.97	2.66	3.6290 (19)	177
C11—H11···Cg2^ix	0.93	2.85	3.641 (4)	144
C12—H12···Cg4^ix	0.93	2.96	3.718 (2)	139

Symmetry codes: (ii) −x+1, −y, −z+1; (iii) −x, −y, −z+1; (vii) x, y+1, z; (ix) −x, −y, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₅N₂O₂⁺.Cl⁻·H₂O
M_r	332.78
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	9.0201 (5), 9.3135 (5), 11.2711 (6)
α, β, γ (°)	66.778 (4), 81.869 (4), 73.656 (4)
V (Å³)	834.50 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.58 × 0.49 × 0.38

Data collection
Diffractometer	Stoe IPDS II diffractometer
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.871, 0.913
No. of measured, independent and observed [I > 2σ(I)] reflections	15618, 3780, 2972
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.122, 1.04
No. of reflections	3780
No. of parameters	214
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.21

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—HW1···Cl1ⁱ	0.93 (3)	2.27 (3)	3.1563 (17)	159 (3)
O3—HW2···Cl1	0.98 (3)	2.22 (3)	3.1848 (17)	168 (3)
C7—H7···O3	0.9300	2.2200	3.133 (2)	168.00
C8—H8A···Cl1ⁱⁱ	0.9700	2.7500	3.7098 (18)	169.00
C8—H8B···Cl1	0.9700	2.6700	3.6371 (18)	173.00
C13—H13A···Cl1ⁱ	0.9700	2.6700	3.6332 (18)	171.00
C13—H13B···Cl1ⁱⁱⁱ	0.9700	2.6600	3.6290 (19)	177.00
C11—H11···Cg2^iv	0.93	2.85	3.641 (4)	144
C12—H12···Cg4^iv	0.93	2.96	3.718 (2)	139

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x, −y, −z+1; (iii) x, y+1, z; (iv) −x, −y, −z+2.

Acknowledgements

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 No. F279 of the University Research Fund). NŞ, SD and HK wish to thank the İnönü University Research Fund (directed project BAPB-2008/05) for financial support of this study.

References

Akkurt, M., Pınar, Ş., Yılmaz, Ü., Küçükbay, H. & Büyükgüngör, O. (2007). Acta Cryst. E63, o379–o381. Web of Science CSD CrossRef IUCr Journals Google Scholar
Akkurt, M., Türktekin, S., Şireci, N., Küçükbay, H. & Büyükgüngör, O. (2006). Acta Cryst. E62, o185–o187. Web of Science CSD CrossRef IUCr Journals Google Scholar
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Altomare, A., Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Rizzi, R. (1999). J. Appl. Cryst. 32, 339–340. Web of Science CrossRef CAS IUCr Journals Google Scholar
Çetinkaya, B., Çetinkaya, E., Küçükbay, H. & Durmaz, R. (1996). Arzneim. Forsch. Drug Res. 46, 821–823. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Ji, K. G., Shu, X. Z., Chen, J., Zhao, S. C., Zheng, Z. J., Liu, X. Y. & Liang, Y. M. (2009). Org. Biomol. Chem. 7, 2501–2505. Web of Science CrossRef PubMed CAS Google Scholar
Küçükbay, H., Çetinkaya, B., Guesmi, S. & Dixneuf, P. H. (1996). Organometallics, 15, 2434–2439. CrossRef CAS Web of Science Google Scholar
Küçükbay, H. & Durmaz, B. (1997). Arzneim. Forsch. Drug Res. 47, 667–670. Google Scholar
Küçükbay, H., Durmaz, R., Güven, M. & Günal, S. (2001). Arzneim. Forsch. Drug Res. 51, 420–424. CAS Google Scholar
Küçükbay, H., Durmaz, R., Okuyucu, N., Günal, S. & Kazaz, C. (2004). Arzneim. Forsch. Drug Res. 54, 64–68. Google Scholar
Küçükbay, H., Durmaz, R., Şireci, N. & Günal, S. (2009). Asian J. Chem. 21, 6181–6189. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany. Google Scholar
Yıldırım, S. Ö., Akkurt, M., Şireci, N., Küçükbay, H. & Kazak, C. (2007). Acta Cryst. E63, o2433. Web of Science CSD CrossRef IUCr Journals Google Scholar