3-Chloro-6-{4-[3-(trifluoro­meth­yl)phen­yl]piperazin-1-yl}pyridazine

Arslan, H.; Utku, S.; Hardcastle, K.I.; Gökçe, M.; Lense, S.

doi:10.1107/S1600536810004137

organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page o532

doi:10.1107/S1600536810004137

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3-Chloro-6-{4-[3-(trifluoromethyl)phenyl]piperazin-1-yl}pyridazine

Hakan Arslan,^a,^b ^* Semra Utku,^c Kenneth I. Hardcastle,^a Mehtap Gökçe ^d and Sheri Lense ^a

^aDepartment of Chemistry, Emory University, Atlanta, GA 30322, USA, ^bDepartment of Chemistry, Faculty of Arts and Science, Mersin University, Mersin, TR-33343, Turkey, ^cDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Mersin University, Mersin, TR-33169, Turkey, and ^dDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Gazi University, Ankara, TR-06330, Turkey
^*Correspondence e-mail: hakan.arslan.acad@gmail.com

(Received 1 February 2010; accepted 2 February 2010; online 6 February 2010)

The title compound, C₁₅H₁₄ClF₃N₄, was synthesized from 3,6-dichloropyridazine and 1-[3-(trifluoromethyl)phenyl]piperazine. The piperazine ring is flanked by 3-chloropyridazine and 3-trifluoromethylphenyl rings and adopts a chair conformation, whereas the 3-chloropyridazine and 3-trifluoromethylphenyl rings are planar, with maximum deviations of 0.0069 (13) and 0.0133 (14) Å, respectively. The crystal structure is stabilized by weak intermolecular C—H⋯N hydrogen-bond interactions.

Related literature

For the synthesis and analgesic and anti-inflammatory activity of pyridazinone and pyridazine derivatives, see: Arslan et al. (2010 ); Giri & Mukhopadhyay (1998 ); Boissier et al. (1963 ); Gokce et al. (2001 , 2004 , 2005 , 2009 ); Sahin et al. (2004 ); Dundar et al. (2007 ). For general background to pyrazolone derivatives, see: Amir et al. (2008 ); Banoglu et al. (2004 ). For puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₅H₁₄ClF₃N₄
M_r = 342.75
Monoclinic, P 2₁ /c
a = 9.461 (6) Å
b = 6.557 (4) Å
c = 24.123 (16) Å
β = 99.890 (9)°
V = 1474.1 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 173 K
0.41 × 0.25 × 0.24 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.888, T_max = 0.932
19935 measured reflections
3385 independent reflections
2781 reflections with I > 2σ(I)
R_int = 0.065

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.101
S = 1.06
3385 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11B⋯N4ⁱ	0.99	2.69	3.628 (2)	158
Symmetry code: (i) x, y-1, z.

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810004137/hg2643sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810004137/hg2643Isup2.hkl

checkCIF report

Comment top

It is known that some pyrazolone derivatives like oxyphenbutazone, dipyrone, antipyrine and phenylbutazone are used primarily for their anti-inflammatory, antipyretic and analgesic activities, but several side effects have limited the clinical use of these drugs such as some of pyrazolone derivatives are toxic and carcinogenicin animals, clastogenic in somatic and germ cells of male mice, and also weakly mutagenic in Salmonella strain TA100 in presence of rat liver homogenate. In addition, some of pyrazolone derivatives induce peptic ulcer, hypersensitivity reaction, hepatitis, nephritis and bone marrow suppression (Giri & Mukhopadhyay, 1998).

Pyridazinone derivatives are structurally related to pyrazolone derivatives (Gokce et al., 2009). Many pyridazinone derivatives have been reported as analgesic and anti-inflammatory agents without gastrointestinal side effect (Amir et al., 2008, Banoglu et al., 2004, Gokce et al., 2009). This is agreement with in our experience in the pyridazinone field. (Dundar et al., 2007; Gokce et al., 2001, 2004, 2005, 2009; Sahin et al., 2004).

Recently, our research has focussed on the chemical, physical and biologycal properties of pyridazinone derivatives (Gokce et al., 2009, Arslan et al., 2010). The title compound, 3-chloro-6-{4-[3-(trifluoromethyl)phenyl]piperazin-1-yl}pyridazine, I, Scheme 1, is an example and in this article, we report on the crystal structure of the title compound, Figure 1.

The molecular structure of I consists of 3-chloropyridazine and 3-trifluoromethylphenyl arms connected to a piperazine ring. The 3-chloropyridazine and 3-trifluoromethylphenyl rings are planar with a maximum deviation of -0.0069 (13) Å for atom C7 and -0.0133 (14) Å for atom C3. The dihedral angle between these two rings is 18.77 (6) °. The piperazine ring adopts a chair conformation. This is confirmed by the puckering parameters q₂ = 0.0107 (14) Å, q₃= 0.5479 (13) Å, Q_T = 0.5480 (13) Å, θ = 1.05 (15) ° and ϕ= 85 (7) ° (Cremer & Pople, 1975).

The conformations of the 3-chloropyridazine and 3-trifluoromethylphenyl rings are best described by the torsion angles of 159.40 (11) ° and -165.62 (11) ° for C7—N2—C6—C5 and C4—N1—C12—C11, respectively; thus they adopt + antiperiplanar and - antiperiplanar conformations, respectively.

The crystal packing is dominated by weak intermolecular C11—H11B···N4 (x, y-1, z) hydrogen bonds, with H···N = 2.69 Å and a C—H···N angle of 150 ° (Figure 2).

Related literature top

For the synthesis and analgesic and anti-inflammatory activity of pyridazinone and pyridazine derivatives, see: Arslan et al. (2010); Giri & Mukhopadhyay (1998); Boissier et al. (1963); Gokce et al. (2001, 2004, 2005, 2009); Sahin et al. (2004); Dundar et al. (2007). For general background to pyrazolone derivatives, see: Amir et al. (2008); Banoglu et al. (2004). For puckering parameters, see: Cremer & Pople (1975).

Experimental top

A mixture of 3,6-dichloropyridazine, II, (1.7 mol) and 1-[3-(trifluoromethyl)phenyl]piperazine, III, (2.0 mol) in ethanol (10 ml) was heated under reflux for 4 hours after which the mixture was cooled to room temperature (Figure 3) (Boissier et al. (1963)). The resulting crude precipitate was filtered off and purified by repeated washing with small portions of cold ethanol. The precipitate formed was crystallized from CH₂Cl₂: ethanol (5:10 ml) to give the compound, 3-chloro-6-{4-[3-(trifluoromethyl)phenyl]piperazin-1-yl}pyridazine, I, as white crystals. Yields: 0.485 g, 83%. M.p.: 167 °C. ¹H-NMR (DMSO-d₆) δ: 7.56-7.54 (d, 1H, pyridazin), 7.46-7.40 (m, 2H, phenyl), 7.28-7.21 (m, 1H, phenyl), 7.14-7.12 (d, 1H, phenyl), 7.09-7.07 (d, 1H, pyridazin), 3.74-3.71 (t, 2H, piperazine), 3.45-3.43 (t, 2H, piperazine), 3.19-3.17 (t, 4H, piperazine). MS (EI) m/z: 343 (M⁺). Anal. Calc. for C₁₅H₁₄N₄ClF₃: C, 52.56; H, 4.12; N, 16.35%. Found: C, 52.61; H, 4.09; N, 16.40%.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), showing ellipsoids at the 50% probability level.
	Fig. 2. The molecular packing of (I). The hydrogen bonds are shown as dashed lines.
	Fig. 3. Synthesis of the title compound.

3-Chloro-6-{4-[3-(trifluoromethyl)phenyl]piperazin-1-yl}pyridazine top

Crystal data top

C₁₅H₁₄ClF₃N₄	F(000) = 704
M_r = 342.75	D_x = 1.544 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7857 reflections
a = 9.461 (6) Å	θ = 2.2–29.7°
b = 6.557 (4) Å	µ = 0.30 mm⁻¹
c = 24.123 (16) Å	T = 173 K
β = 99.890 (9)°	Block, colourless
V = 1474.1 (16) Å³	0.41 × 0.25 × 0.24 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	3385 independent reflections
Radiation source: fine-focus sealed tube	2781 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.065
ϕ and ω scans	θ_max = 27.5°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −12→12
T_min = 0.888, T_max = 0.932	k = −8→8
19935 measured reflections	l = −31→31

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.101	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0589P)² + 0.1216P] where P = (F_o² + 2F_c²)/3
3385 reflections	(Δ/σ)_max = 0.005
208 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₅H₁₄ClF₃N₄	V = 1474.1 (16) Å³
M_r = 342.75	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.461 (6) Å	µ = 0.30 mm⁻¹
b = 6.557 (4) Å	T = 173 K
c = 24.123 (16) Å	0.41 × 0.25 × 0.24 mm
β = 99.890 (9)°

Data collection top

Bruker APEXII CCD diffractometer	3385 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	2781 reflections with I > 2σ(I)
T_min = 0.888, T_max = 0.932	R_int = 0.065
19935 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.101	H-atom parameters constrained
S = 1.06	Δρ_max = 0.32 e Å⁻³
3385 reflections	Δρ_min = −0.23 e Å⁻³
208 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) 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
C1	1.35124 (16)	0.4693 (2)	0.76675 (6)	0.0301 (3)
C2	1.23214 (15)	0.35744 (19)	0.78778 (5)	0.0228 (3)
C3	1.15571 (14)	0.45817 (19)	0.82401 (5)	0.0212 (3)
H3	1.1811	0.5939	0.8354	0.025*
C4	1.04104 (14)	0.36134 (18)	0.84400 (5)	0.0194 (3)
C5	1.01095 (15)	0.65546 (17)	0.90409 (6)	0.0235 (3)
H5A	1.0563	0.7374	0.8775	0.028*
H5B	1.0856	0.6219	0.9368	0.028*
C6	0.89367 (15)	0.78043 (18)	0.92372 (6)	0.0241 (3)
H6A	0.9364	0.9031	0.9439	0.029*
H6B	0.8240	0.8262	0.8906	0.029*
C7	0.74380 (13)	0.76537 (18)	0.99646 (5)	0.0186 (3)
C8	0.62135 (14)	0.9883 (2)	1.06758 (5)	0.0220 (3)
C9	0.60062 (14)	0.7770 (2)	1.06879 (5)	0.0236 (3)
H6	0.5458	0.7163	1.0939	0.028*
C10	0.66253 (14)	0.66193 (19)	1.03229 (5)	0.0221 (3)
H10	0.6517	0.5179	1.0309	0.027*
C11	0.76124 (14)	0.47012 (18)	0.93414 (6)	0.0223 (3)
H11A	0.6846	0.5022	0.9019	0.027*
H11B	0.7183	0.3881	0.9614	0.027*
C12	0.87797 (15)	0.34660 (18)	0.91356 (6)	0.0226 (3)
H12A	0.9476	0.2987	0.9464	0.027*
H12B	0.8344	0.2250	0.8930	0.027*
C13	1.01216 (15)	0.15733 (18)	0.82706 (5)	0.0238 (3)
H13	0.9365	0.0862	0.8399	0.029*
C14	1.09205 (16)	0.05852 (19)	0.79199 (5)	0.0277 (3)
H14	1.0708	−0.0796	0.7819	0.033*
C15	1.20215 (16)	0.1564 (2)	0.77128 (6)	0.0268 (3)
H15	1.2552	0.0886	0.7467	0.032*
Cl1	0.54631 (4)	1.14481 (6)	1.113190 (14)	0.03333 (13)
F1	1.47712 (10)	0.45600 (17)	0.80245 (4)	0.0510 (3)
F2	1.37526 (11)	0.39838 (16)	0.71726 (4)	0.0517 (3)
F3	1.32478 (10)	0.66983 (13)	0.75974 (4)	0.0438 (3)
N1	0.95396 (11)	0.46588 (15)	0.87639 (4)	0.0201 (2)
N2	0.81888 (12)	0.66056 (15)	0.96101 (4)	0.0201 (2)
N3	0.75776 (12)	0.96974 (15)	0.99729 (4)	0.0233 (3)
N4	0.69511 (12)	1.08204 (16)	1.03382 (5)	0.0248 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0290 (8)	0.0347 (7)	0.0294 (7)	−0.0006 (6)	0.0132 (6)	−0.0075 (6)
C2	0.0230 (7)	0.0259 (6)	0.0203 (6)	0.0020 (5)	0.0054 (5)	−0.0013 (5)
C3	0.0239 (7)	0.0189 (6)	0.0219 (6)	−0.0001 (5)	0.0065 (5)	−0.0028 (5)
C4	0.0236 (7)	0.0184 (6)	0.0163 (6)	0.0026 (5)	0.0040 (5)	0.0014 (4)
C5	0.0269 (7)	0.0156 (6)	0.0314 (7)	−0.0049 (5)	0.0147 (6)	−0.0026 (5)
C6	0.0318 (8)	0.0149 (5)	0.0298 (7)	−0.0027 (5)	0.0175 (6)	0.0001 (5)
C7	0.0176 (7)	0.0194 (6)	0.0189 (6)	−0.0007 (5)	0.0032 (5)	0.0011 (4)
C8	0.0196 (7)	0.0285 (6)	0.0181 (6)	0.0016 (5)	0.0038 (5)	−0.0036 (5)
C9	0.0201 (7)	0.0307 (7)	0.0211 (6)	−0.0022 (5)	0.0063 (5)	0.0041 (5)
C10	0.0225 (7)	0.0202 (6)	0.0244 (6)	−0.0025 (5)	0.0063 (5)	0.0031 (5)
C11	0.0231 (7)	0.0182 (6)	0.0274 (7)	−0.0055 (5)	0.0094 (5)	−0.0023 (5)
C12	0.0281 (8)	0.0144 (5)	0.0278 (7)	−0.0037 (5)	0.0118 (6)	−0.0007 (5)
C13	0.0314 (8)	0.0186 (6)	0.0226 (6)	−0.0027 (5)	0.0081 (6)	0.0012 (5)
C14	0.0415 (9)	0.0184 (6)	0.0237 (6)	0.0011 (6)	0.0073 (6)	−0.0026 (5)
C15	0.0324 (8)	0.0258 (7)	0.0237 (7)	0.0055 (5)	0.0089 (6)	−0.0042 (5)
Cl1	0.0347 (2)	0.0404 (2)	0.0277 (2)	0.00403 (15)	0.01307 (16)	−0.00988 (14)
F1	0.0271 (6)	0.0704 (7)	0.0556 (6)	−0.0063 (5)	0.0077 (5)	0.0012 (5)
F2	0.0615 (7)	0.0616 (6)	0.0419 (6)	−0.0158 (5)	0.0369 (5)	−0.0197 (5)
F3	0.0458 (6)	0.0321 (5)	0.0617 (6)	−0.0037 (4)	0.0324 (5)	0.0035 (4)
N1	0.0250 (6)	0.0148 (5)	0.0228 (5)	−0.0022 (4)	0.0107 (5)	−0.0010 (4)
N2	0.0239 (6)	0.0144 (5)	0.0246 (6)	−0.0032 (4)	0.0115 (5)	0.0001 (4)
N3	0.0279 (7)	0.0186 (5)	0.0261 (6)	−0.0026 (4)	0.0121 (5)	−0.0027 (4)
N4	0.0279 (7)	0.0225 (5)	0.0258 (6)	−0.0017 (5)	0.0096 (5)	−0.0057 (4)

Geometric parameters (Å, º) top

C1—F2	1.3364 (16)	C8—N4	1.3129 (17)
C1—F3	1.3439 (18)	C8—C9	1.400 (2)
C1—F1	1.3472 (18)	C8—Cl1	1.7425 (14)
C1—C2	1.504 (2)	C9—C10	1.3654 (18)
C2—C15	1.3920 (19)	C9—H6	0.9500
C2—C3	1.3928 (18)	C10—H10	0.9500
C3—C4	1.4114 (18)	C11—N2	1.4681 (17)
C3—H3	0.9500	C11—C12	1.5199 (18)
C4—N1	1.4073 (16)	C11—H11A	0.9900
C4—C13	1.4115 (18)	C11—H11B	0.9900
C5—N1	1.4691 (17)	C12—N1	1.4676 (16)
C5—C6	1.5190 (18)	C12—H12A	0.9900
C5—H5A	0.9900	C12—H12B	0.9900
C5—H5B	0.9900	C13—C14	1.3878 (19)
C6—N2	1.4650 (16)	C13—H13	0.9500
C6—H6A	0.9900	C14—C15	1.388 (2)
C6—H6B	0.9900	C14—H14	0.9500
C7—N3	1.3462 (17)	C15—H15	0.9500
C7—N2	1.3845 (16)	N3—N4	1.3600 (15)
C7—C10	1.4236 (17)

F2—C1—F3	106.53 (12)	C10—C9—H6	121.4
F2—C1—F1	106.34 (12)	C8—C9—H6	121.4
F3—C1—F1	105.59 (12)	C9—C10—C7	117.68 (12)
F2—C1—C2	112.59 (12)	C9—C10—H10	121.2
F3—C1—C2	112.66 (11)	C7—C10—H10	121.2
F1—C1—C2	112.60 (13)	N2—C11—C12	111.21 (11)
C15—C2—C3	121.75 (12)	N2—C11—H11A	109.4
C15—C2—C1	119.53 (12)	C12—C11—H11A	109.4
C3—C2—C1	118.72 (12)	N2—C11—H11B	109.4
C2—C3—C4	120.89 (12)	C12—C11—H11B	109.4
C2—C3—H3	119.6	H11A—C11—H11B	108.0
C4—C3—H3	119.6	N1—C12—C11	112.04 (11)
N1—C4—C13	121.30 (11)	N1—C12—H12A	109.2
N1—C4—C3	121.89 (11)	C11—C12—H12A	109.2
C13—C4—C3	116.70 (11)	N1—C12—H12B	109.2
N1—C5—C6	111.56 (11)	C11—C12—H12B	109.2
N1—C5—H5A	109.3	H12A—C12—H12B	107.9
C6—C5—H5A	109.3	C14—C13—C4	121.34 (12)
N1—C5—H5B	109.3	C14—C13—H13	119.3
C6—C5—H5B	109.3	C4—C13—H13	119.3
H5A—C5—H5B	108.0	C15—C14—C13	121.65 (12)
N2—C6—C5	110.97 (11)	C15—C14—H14	119.2
N2—C6—H6A	109.4	C13—C14—H14	119.2
C5—C6—H6A	109.4	C14—C15—C2	117.62 (12)
N2—C6—H6B	109.4	C14—C15—H15	121.2
C5—C6—H6B	109.4	C2—C15—H15	121.2
H6A—C6—H6B	108.0	C4—N1—C12	118.34 (10)
N3—C7—N2	116.34 (10)	C4—N1—C5	117.42 (11)
N3—C7—C10	121.81 (11)	C12—N1—C5	110.68 (10)
N2—C7—C10	121.77 (12)	C7—N2—C6	117.79 (10)
N4—C8—C9	124.58 (11)	C7—N2—C11	120.25 (11)
N4—C8—Cl1	115.68 (10)	C6—N2—C11	111.53 (10)
C9—C8—Cl1	119.73 (10)	C7—N3—N4	119.73 (10)
C10—C9—C8	117.13 (12)	C8—N4—N3	119.05 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11B···N4ⁱ	0.99	2.69	3.628 (2)	158

Symmetry code: (i) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄ClF₃N₄
M_r	342.75
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	9.461 (6), 6.557 (4), 24.123 (16)
β (°)	99.890 (9)
V (Å³)	1474.1 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.30
Crystal size (mm)	0.41 × 0.25 × 0.24

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.888, 0.932
No. of measured, independent and observed [I > 2σ(I)] reflections	19935, 3385, 2781
R_int	0.065
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.101, 1.06
No. of reflections	3385
No. of parameters	208
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.23

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11B···N4ⁱ	0.99	2.69	3.628 (2)	158

Symmetry code: (i) x, y−1, z.

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Volume 66| Part 3| March 2010| Page o532

doi:10.1107/S1600536810004137

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