3-Anilinomethyl-5-chloro-1,3-­benzoxazol-2(3H)-one

Aydın, A.; Soyer, Z.; Akkurt, M.; Büyükgüngör, O.

doi:10.1107/S1600536812017709

organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Pages o1544-o1545

doi:10.1107/S1600536812017709

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3-Anilinomethyl-5-chloro-1,3-benzoxazol-2(3H)-one

Abdullah Aydın,^a ^* Zeynep Soyer,^b Mehmet Akkurt ^c and Orhan Büyükgüngör ^d

^aDepartment of Science Education, Faculty of Education, Kastamonu University, 37200 Kastamonu, Turkey, ^bDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Ege University, 35100 Ízmir, Turkey, ^cDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, and ^dDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139 Samsun, Turkey
^*Correspondence e-mail: aaydin@kastamonu.edu.tr

(Received 5 April 2012; accepted 20 April 2012; online 28 April 2012)

In the title compound, C₁₄H₁₁ClN₂O₂, the 2,3-dihydro-1,3-benzoxazole ring system is essentially planar [maximum deviation = 0.009 (2) Å] and makes a dihedral angle of 79.15 (7)° with the phenyl ring. Intermolecular N—H⋯O and weak C—H⋯Cl hydrogen bonds occur in the crystal structure.

Related literature

For the synthesis and biological activity of compounds with a benzoxazolone nucleus, see; Varma & Nobles (1968 ); Courtois et al. (2004 ); Deng et al. (2006 ); Ivanova et al. (2007 ); Koksal et al. (2002 , 2005 ); Onkol et al. (2001 ); Soyer et al. (2005 ); Ucar et al. (1998 ); Unlu et al. (2003 ). For bond-length data, see: Allen et al. (1987 ). For a related structure, see: Aydın et al. (2004 ).

Experimental

Crystal data

C₁₄H₁₁ClN₂O₂
M_r = 274.70
Monoclinic, P 2₁ /n
a = 9.7379 (5) Å
b = 12.4797 (7) Å
c = 10.2392 (7) Å
β = 93.129 (5)°
V = 1242.48 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 296 K
0.80 × 0.48 × 0.26 mm

Data collection

Stoe IPDS 2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ) T_min = 0.837, T_max = 0.924
20574 measured reflections
3051 independent reflections
2544 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.106
S = 1.07
3051 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O2ⁱ	0.86	2.30	3.1296 (17)	162
C11—H11⋯Cl1ⁱⁱ	0.93	2.70	3.5295 (17)	150
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) x, y, z+1.

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); 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/S1600536812017709/xu5511sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812017709/xu5511Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812017709/xu5511Isup3.cml

checkCIF report

Comment top

The benzoxazolone nucleus represents an important pharmacophore present in pharmaceutical products. The compounds possessing this structure have a broad spectrum of biological activities, such as anti-HIV (Deng et al., 2006), anticancer (Ivanova et al., 2007), analgesic (Unlu et al., 2003), anti-inflammatory (Koksal et al., 2005), antinociceptive (Onkol et al., 2001), antimicrobial (Koksal et al., 2002), anticonvulsant (Ucar et al., 1998), antimalarial (Courtois et al., 2004), human leukocyte MPO clorinating inhibitor activity (Soyer et al., 2005).

In addition to, this compound was synthesized before by (Varma & Nobles, 1968) and they reported that most benzoxazolinone compounds have shown significant antibacterial activity.

In the title compound (I), (Fig. 1), the mean planes of the 2,3-dihydro-1,3-benzoxazole and phenyl rings make a dihedral angle of 79.15 (7)° with each other. The N1—C8—N2—C9 torsion angle is -72.99 (18)°. The bond lengths in (I) are normal and correspond to those observed in the related compound (Allen et al., 1987).

The Cl1—C3 and N1—C1 bond lengths are 1.7315 (16) Å, and 1.3914 (18) Å, respectively. The Cl1—C3—C4 and O2—C7—N1 bond angles are 118.73 (13) ° and 129.27 (15) °, respectively. The bond lengths and the bond angles of (I) are comparable to those observed in related structure (Aydın et al., 2004).

The crystal structure is stabilized by intermolecular N—H···O and C—H···Cl interactions (Table 1 and Fig. 2), connecting the molecules along the [001] direction.

Related literature top

For the synthesis and biological activity of compounds with a benzoxazolone nucleus, see; Varma & Nobles (1968); Courtois et al. (2004); Deng et al. (2006); Ivanova et al. (2007); Koksal et al. (2002, 2005); Onkol et al. (2001); Soyer et al. (2005); Ucar et al. (1998); Unlu et al. (2003). For bond-length data, see: Allen et al. (1987). For a related structure, see: Aydın et al. (2004).

Experimental top

4-Chloro-2-aminophenol (10 mmol), urea (50 mmol) and 37% HCl (2.5 ml) were irradiated (300 W, 413 K) for 15 min in a microwave oven. After completion of reaction (by monitoring with TLC), water (10 ml) was added to the reaction mixture and stirred at room temperature for 1 h. The resulting precipitate was filtered and washed with water. The crude product crystallized from ethanol-water (1:1) to yield 5-chloro-2(3H)-benzoxazolone. This compound (2 mmol) was dissolved in methanol (5 ml). Aniline (2 mmol) and 37% formalin (2.5 mmol) were added to this solution. The mixture was stirred vigorously for 3 h. The resulting precipitate was filtered and washed with cold methanol. The crude product was crystallized from methanol.

M.p.: 463 K. Yield 84%; IR v_max (FTIR/ATR): 3398, 3066, 1750, 1604 cm^-1; ¹H-NMR (DMSO-d₆): δ 5.23 (2H, d, J=7.0 Hz, CH₂), 6.61(1H, t, J=7.4 Hz, H-Aniline), 6.73-6.75 (2H, m, H-Aniline), 6.96 (1H, t, J=7.3 Hz, NH), 7.09 (2H, t, J=7.4 Hz, H-Aniline) 7.14 (1H, dd, J=2.3; 8.6 Hz, H-Benzoxazolone), 7.31 (1H, d, J=8.6 Hz, H-Benzoxazolone), 7.70 (1H, d, J=2.3 Hz, H-Benzoxazolone) p.p.m.; MS (ESI) m/z (%): 275 (M+H, 11), 277 (M+H+2, 4).

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: SHELXS97 (Sheldrick, 2008); 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 molecule shown with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.
	Fig. 2. The packing and hydrogen bonding of (I) viewed down the a axis. H atoms not involved in hydrogen bondings are omitted for the sake of clarity.

3-Anilinomethyl-5-chloro-1,3-benzoxazol-2(3H)-one top

Crystal data top

C₁₄H₁₁ClN₂O₂	F(000) = 568
M_r = 274.70	D_x = 1.469 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 27572 reflections
a = 9.7379 (5) Å	θ = 2.1–28.6°
b = 12.4797 (7) Å	µ = 0.31 mm⁻¹
c = 10.2392 (7) Å	T = 296 K
β = 93.129 (5)°	Prism, colourless
V = 1242.48 (13) Å³	0.80 × 0.48 × 0.26 mm
Z = 4

Data collection top

Stoe IPDS 2 diffractometer	3051 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	2544 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.046
Detector resolution: 6.67 pixels mm^-1	θ_max = 28.2°, θ_min = 2.6°
ω scans	h = −12→12
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −16→16
T_min = 0.837, T_max = 0.924	l = −13→13
20574 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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.106	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0456P)² + 0.2748P] where P = (F_o² + 2F_c²)/3
3051 reflections	(Δ/σ)_max < 0.001
172 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₄H₁₁ClN₂O₂	V = 1242.48 (13) Å³
M_r = 274.70	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.7379 (5) Å	µ = 0.31 mm⁻¹
b = 12.4797 (7) Å	T = 296 K
c = 10.2392 (7) Å	0.80 × 0.48 × 0.26 mm
β = 93.129 (5)°

Data collection top

Stoe IPDS 2 diffractometer	3051 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	2544 reflections with I > 2σ(I)
T_min = 0.837, T_max = 0.924	R_int = 0.046
20574 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.106	H-atom parameters constrained
S = 1.07	Δρ_max = 0.22 e Å⁻³
3051 reflections	Δρ_min = −0.22 e Å⁻³
172 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
Cl1	0.37199 (5)	0.42730 (6)	−0.40607 (5)	0.0887 (2)
O1	0.61747 (10)	0.34298 (10)	0.11087 (11)	0.0535 (3)
O2	0.52561 (13)	0.24080 (12)	0.26644 (11)	0.0679 (4)
N1	0.41738 (11)	0.26396 (10)	0.06103 (11)	0.0428 (4)
N2	0.16989 (12)	0.24829 (12)	0.04683 (12)	0.0508 (4)
C1	0.45104 (13)	0.32285 (11)	−0.04809 (13)	0.0392 (4)
C2	0.38425 (14)	0.33757 (13)	−0.16827 (14)	0.0454 (4)
C3	0.45056 (16)	0.40463 (14)	−0.25277 (15)	0.0520 (5)
C4	0.57449 (16)	0.45354 (13)	−0.22095 (18)	0.0553 (5)
C5	0.64095 (15)	0.43708 (13)	−0.09935 (17)	0.0539 (5)
C6	0.57568 (14)	0.37153 (12)	−0.01549 (15)	0.0447 (4)
C7	0.51813 (15)	0.27708 (13)	0.15798 (15)	0.0495 (5)
C8	0.29647 (15)	0.19414 (13)	0.06944 (15)	0.0479 (5)
C9	0.11468 (13)	0.31842 (12)	0.13447 (13)	0.0422 (4)
C10	0.17189 (15)	0.33453 (13)	0.26004 (14)	0.0475 (4)
C11	0.10954 (17)	0.40404 (15)	0.34387 (16)	0.0565 (5)
C12	−0.00743 (18)	0.45947 (15)	0.30515 (19)	0.0624 (6)
C13	−0.06427 (19)	0.44406 (16)	0.1809 (2)	0.0659 (6)
C14	−0.00497 (17)	0.37461 (15)	0.09612 (16)	0.0567 (5)
H2	0.30060	0.30500	−0.19140	0.0550*
H2A	0.12430	0.23690	−0.02610	0.0610*
H4	0.61400	0.49800	−0.28140	0.0660*
H5	0.72520	0.46880	−0.07610	0.0650*
H8A	0.30210	0.13680	0.00590	0.0580*
H8B	0.29860	0.16180	0.15570	0.0580*
H10	0.25200	0.29870	0.28780	0.0570*
H11	0.14770	0.41340	0.42830	0.0680*
H12	−0.04750	0.50670	0.36210	0.0750*
H13	−0.14370	0.48100	0.15370	0.0790*
H14	−0.04490	0.36490	0.01240	0.0680*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0635 (3)	0.1420 (6)	0.0602 (3)	0.0059 (3)	−0.0005 (2)	0.0431 (3)
O1	0.0397 (5)	0.0669 (7)	0.0528 (6)	−0.0022 (5)	−0.0074 (4)	−0.0061 (5)
O2	0.0674 (8)	0.0890 (9)	0.0457 (6)	0.0034 (7)	−0.0112 (5)	0.0084 (6)
N1	0.0373 (6)	0.0508 (7)	0.0399 (6)	−0.0004 (5)	−0.0007 (4)	0.0013 (5)
N2	0.0387 (6)	0.0736 (9)	0.0397 (6)	−0.0032 (6)	−0.0006 (5)	−0.0068 (6)
C1	0.0332 (6)	0.0416 (7)	0.0429 (7)	0.0030 (5)	0.0039 (5)	−0.0028 (6)
C2	0.0337 (6)	0.0572 (9)	0.0452 (7)	0.0012 (6)	0.0011 (5)	0.0028 (6)
C3	0.0433 (7)	0.0645 (10)	0.0486 (8)	0.0091 (7)	0.0050 (6)	0.0111 (7)
C4	0.0468 (8)	0.0528 (9)	0.0678 (10)	0.0010 (7)	0.0166 (7)	0.0096 (8)
C5	0.0391 (7)	0.0515 (9)	0.0716 (10)	−0.0055 (6)	0.0082 (7)	−0.0054 (8)
C6	0.0353 (6)	0.0478 (8)	0.0507 (8)	0.0027 (6)	0.0002 (6)	−0.0068 (6)
C7	0.0431 (7)	0.0582 (9)	0.0464 (8)	0.0066 (7)	−0.0044 (6)	−0.0024 (7)
C8	0.0477 (8)	0.0487 (8)	0.0476 (8)	−0.0050 (6)	0.0049 (6)	0.0000 (6)
C9	0.0365 (6)	0.0503 (8)	0.0400 (7)	−0.0100 (6)	0.0033 (5)	0.0036 (6)
C10	0.0385 (7)	0.0609 (9)	0.0427 (7)	−0.0069 (6)	−0.0008 (5)	0.0020 (7)
C11	0.0523 (9)	0.0708 (11)	0.0463 (8)	−0.0130 (8)	0.0010 (6)	−0.0104 (8)
C12	0.0565 (9)	0.0612 (10)	0.0704 (11)	−0.0046 (8)	0.0110 (8)	−0.0156 (9)
C13	0.0523 (9)	0.0667 (11)	0.0778 (12)	0.0099 (8)	−0.0039 (8)	−0.0028 (9)
C14	0.0493 (8)	0.0695 (11)	0.0501 (8)	0.0016 (7)	−0.0081 (7)	0.0007 (8)

Geometric parameters (Å, º) top

Cl1—C3	1.7315 (16)	C9—C14	1.398 (2)
O1—C6	1.3817 (19)	C9—C10	1.388 (2)
O1—C7	1.3769 (19)	C10—C11	1.384 (2)
O2—C7	1.198 (2)	C11—C12	1.373 (2)
N1—C1	1.3914 (18)	C12—C13	1.373 (3)
N1—C7	1.3669 (19)	C13—C14	1.376 (3)
N1—C8	1.4711 (19)	C2—H2	0.9300
N2—C8	1.414 (2)	C4—H4	0.9300
N2—C9	1.3831 (19)	C5—H5	0.9300
N2—H2A	0.8600	C8—H8A	0.9700
C1—C2	1.3725 (19)	C8—H8B	0.9700
C1—C6	1.3818 (19)	C10—H10	0.9300
C2—C3	1.388 (2)	C11—H11	0.9300
C3—C4	1.376 (2)	C12—H12	0.9300
C4—C5	1.387 (2)	C13—H13	0.9300
C5—C6	1.368 (2)	C14—H14	0.9300

C6—O1—C7	107.78 (11)	C9—C10—C11	119.87 (14)
C1—N1—C7	109.19 (11)	C10—C11—C12	121.47 (16)
C1—N1—C8	125.75 (11)	C11—C12—C13	118.90 (17)
C7—N1—C8	124.99 (12)	C12—C13—C14	120.73 (17)
C8—N2—C9	124.23 (12)	C9—C14—C13	120.73 (15)
C9—N2—H2A	118.00	C1—C2—H2	122.00
C8—N2—H2A	118.00	C3—C2—H2	122.00
N1—C1—C6	106.29 (12)	C3—C4—H4	120.00
N1—C1—C2	132.05 (12)	C5—C4—H4	120.00
C2—C1—C6	121.65 (13)	C4—C5—H5	122.00
C1—C2—C3	115.20 (13)	C6—C5—H5	122.00
Cl1—C3—C4	118.73 (13)	N1—C8—H8A	109.00
Cl1—C3—C2	117.77 (12)	N1—C8—H8B	109.00
C2—C3—C4	123.49 (15)	N2—C8—H8A	109.00
C3—C4—C5	120.48 (15)	N2—C8—H8B	109.00
C4—C5—C6	116.25 (14)	H8A—C8—H8B	108.00
C1—C6—C5	122.93 (14)	C9—C10—H10	120.00
O1—C6—C5	128.24 (13)	C11—C10—H10	120.00
O1—C6—C1	108.83 (12)	C10—C11—H11	119.00
O1—C7—N1	107.90 (12)	C12—C11—H11	119.00
O1—C7—O2	122.84 (14)	C11—C12—H12	121.00
O2—C7—N1	129.27 (15)	C13—C12—H12	121.00
N1—C8—N2	113.63 (13)	C12—C13—H13	120.00
N2—C9—C10	122.83 (13)	C14—C13—H13	120.00
C10—C9—C14	118.29 (14)	C9—C14—H14	120.00
N2—C9—C14	118.87 (13)	C13—C14—H14	120.00

C7—O1—C6—C5	179.00 (16)	N1—C1—C2—C3	179.08 (15)
C6—O1—C7—O2	−178.94 (16)	C6—C1—C2—C3	−0.3 (2)
C7—O1—C6—C1	−0.57 (16)	N1—C1—C6—O1	0.04 (16)
C6—O1—C7—N1	0.88 (16)	C2—C1—C6—C5	0.0 (2)
C7—N1—C1—C2	−178.96 (16)	C1—C2—C3—Cl1	−179.79 (12)
C8—N1—C1—C2	3.9 (2)	C1—C2—C3—C4	0.2 (2)
C1—N1—C7—O1	−0.86 (16)	C2—C3—C4—C5	0.3 (3)
C8—N1—C7—O1	176.31 (13)	Cl1—C3—C4—C5	−179.75 (13)
C1—N1—C7—O2	178.93 (17)	C3—C4—C5—C6	−0.6 (2)
C8—N1—C7—O2	−3.9 (3)	C4—C5—C6—C1	0.5 (2)
C1—N1—C8—N2	−59.57 (18)	C4—C5—C6—O1	−179.03 (15)
C7—N1—C8—N2	123.72 (15)	N2—C9—C10—C11	−178.47 (15)
C8—N1—C1—C6	−176.64 (13)	C14—C9—C10—C11	0.6 (2)
C7—N1—C1—C6	0.51 (16)	N2—C9—C14—C13	179.13 (16)
C8—N2—C9—C10	−6.8 (2)	C10—C9—C14—C13	0.0 (2)
C9—N2—C8—N1	−72.99 (18)	C9—C10—C11—C12	−1.1 (3)
C8—N2—C9—C14	174.17 (15)	C10—C11—C12—C13	0.9 (3)
C2—C1—C6—O1	179.57 (13)	C11—C12—C13—C14	−0.3 (3)
N1—C1—C6—C5	−179.55 (14)	C12—C13—C14—C9	−0.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2ⁱ	0.86	2.30	3.1296 (17)	162
C11—H11···Cl1ⁱⁱ	0.93	2.70	3.5295 (17)	150

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₁ClN₂O₂
M_r	274.70
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	9.7379 (5), 12.4797 (7), 10.2392 (7)
β (°)	93.129 (5)
V (Å³)	1242.48 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.31
Crystal size (mm)	0.80 × 0.48 × 0.26

Data collection
Diffractometer	Stoe IPDS 2 diffractometer
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.837, 0.924
No. of measured, independent and observed [I > 2σ(I)] reflections	20574, 3051, 2544
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.664

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.106, 1.07
No. of reflections	3051
No. of parameters	172
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.22

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 2008), 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
N2—H2A···O2ⁱ	0.86	2.30	3.1296 (17)	162
C11—H11···Cl1ⁱⁱ	0.93	2.70	3.5295 (17)	150

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

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS 2 diffractometer (purchased under grant F.279 of the University Research Fund).

References

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
Aydın, A., Önkol, T., Akkurt, M., Büyükgüngör, O. & Ünlü, S. (2004). Acta Cryst. E60, o244–o245. Web of Science CSD CrossRef IUCr Journals Google Scholar
Courtois, M., Mincheva, Z., Andreu, F., Rideau, M. & Viaud-Massuard, M. C. (2004). J. Enzyme Inhib. Med. Chem. 19, 559–565. Web of Science CrossRef PubMed CAS Google Scholar
Deng, B. L., Cullen, M. D., Zhou, Z., Hartman, T. L., Buckheit, R. W. Jr, Pannecouque, C., Clercq, E. D., Fanwick, P. E. & Cushman, M. (2006). Bioorg. Med. Chem. 14, 2366–2374. Web of Science CSD CrossRef PubMed CAS 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
Ivanova, Y., Momekov, G., Petrov, O., Karaivanova, M. & Kalcheva, V. (2007). Eur. J. Med. Chem. 42, 1382–1387. Web of Science CrossRef PubMed CAS Google Scholar
Koksal, M., Gokhan, N., Erdogan, H., Ozalp, M. & Ekizoglu, M. (2002). Il Farmaco, 57, 535–538. Web of Science PubMed CAS Google Scholar
Koksal, M., Gokhan, N., Kupeli, E., Yesilada, E. & Erdogan, H. (2005). Arch. Pharm. Chem. Life Sci. 338, 117–125. CAS Google Scholar
Onkol, T., Ito, S., Yildirim, E., Erol, K. & Sahin, M. F. (2001). Arch. Pharm. Pharm. Med. Chem. 334, 17–20. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Soyer, Z., Bas, M., Pabuccuoglu, A. & Pabuccuoglu, V. (2005). Arch. Pharm. Chem. Life Sci. 338, 405–410. Web of Science CrossRef CAS 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
Ucar, H., Vanderpoorten, K., Cacciaguerra, S., Spampinato, S., Stables, J. P., Depovere, P., Isa, M., Masereel, B., Delarge, J. & Poupaert, J. H. (1998). J. Med. Chem. 41, 1138–1145. Web of Science CrossRef CAS PubMed Google Scholar
Unlu, S., Onkol, T., Dundar, Y., Okcelik, B., Kupeli, E., Yesilada, E., Noyanalpan, N. & Sahin, M. F. (2003). Arch. Pharm. Pharm. Med. Chem. 336, 353–361. Google Scholar
Varma, R. S. & Nobles, W. L. (1968). J. Pharm. Sci. 57, 39–44. CrossRef CAS PubMed Web of Science Google Scholar