(E)-3-Hydr­oxy-N′-(2-hydroxy­benzyl­idene)-2-naphthohydrazide

Monfared, H.H.; Bikas, R.; Mayer, P.

doi:10.1107/S1600536809053793

organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Pages o236-o237

doi:10.1107/S1600536809053793

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(E)-3-Hydroxy-N′-(2-hydroxybenzylidene)-2-naphthohydrazide

Hassan Hosseini Monfared,^a ^* Rahman Bikas ^a and Peter Mayer ^b

^aDepartment of Chemistry, Zanjan University 45195-313, Zanjan, Islamic Republic of Iran, and ^bDepartment of Chemistry and Biochemistry, Ludwig-Maximilians-Universität, Butenandtstrasse 5–13, 81377 München, Germany
^*Correspondence e-mail: monfared@znu.ac.ir

(Received 3 November 2009; accepted 14 December 2009; online 24 December 2009)

The title compound, C₁₈H₁₄N₂O₃, is an aroylhydrazone with an approximately planar structure [dihedral angle of 15.27 (13)° between the benzene ring and the naphthyl ring system], stabilized by intramolecular N—H⋯O and O—H⋯N hydrogen bonds. Intermolecular O—H⋯O hydrogen bonds with the keto group as acceptor lead to strands along [100]. In terms of graph-set analysis, the descriptor on the unitary level is C₁¹(6)S(6)S(6).

Related literature

For historical background to aroylhydrazones, see: Savanini et al. (2002 ); Craliz et al. (1955 ); Pickart et al. (1983 ); Offe et al. (1952 ); Arapov et al. (1987 ); Ranford et al. (1998 ). For related structures, see: Liu et al. (2004 ); Lei et al. (2008 ). For graph-set analysis of hydrogen-bond networks, see: Bernstein et al. (1995 ); Etter et al. (1990 ).

Experimental

Crystal data

C₁₈H₁₄N₂O₃
M_r = 306.32
Orthorhombic, P n a 2₁
a = 12.6749 (4) Å
b = 4.9666 (1) Å
c = 22.7299 (6) Å
V = 1430.87 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 200 K
0.50 × 0.10 × 0.09 mm

Data collection

Nonius KappaCCD diffractometer
10328 measured reflections
1676 independent reflections
1416 reflections with I > 2σ(I)
R_int = 0.054

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.095
S = 1.09
1676 reflections
220 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N2	0.96 (5)	1.87 (5)	2.697 (3)	142 (4)
O3—H3⋯O1ⁱ	0.84 (4)	1.81 (4)	2.609 (2)	157 (3)
N1—H1⋯O3	0.92 (3)	1.85 (3)	2.628 (3)	141 (2)
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ .

Data collection: COLLECT (Hooft, 2004 ); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809053793/bg2308sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809053793/bg2308Isup2.hkl

checkCIF report

Comment top

As part of our studies on the synthesis and characterization of aroylhydrazone derivatives, we report on the crystal structure of (E)-3-hydroxy-N'-(2-hydroxybenzylidene)-2-naphthohydrazide.

The asymmetric unit contains one molecule of the title compound, which is shown in Figure 1. The molecule is almost planar with a dihedral angle of 15.27 (13)° between the benzene ring and the naphthyl ring. This configuration is stabilized by two intramolecular hydrogen bonds of the types O–H···N and N–H···O. The keto group acts as an acceptor in a hydrogen bond of the type O–H···O leading to infinite chains along [100] (Fig. 2). In terms of graph-set analysis [Bernstein et al. (1995), Etter et al. (1990)], the descriptor on the unitary level is C₁¹(6)S(6)S(6).

The arrangement of the molecules within the chains along [100] formed by hydrogen bonds becomes evident when viewing along the chain axis (Fig. 3). The chains are constituted by the glide planes perpendicular to the b-axis with the glide vectors along [100]. Since the title compound is not oriented parallel or perpendicular to the glide plane, the hydrogen-bond linked molecules do not form layers as one might think when seeing Fig. 2. The repeating unit of the chain consists of two molecules which are oriented approximately perpendicular to each other. The least-square planes (determined by all non-hydrogen atoms of a molecule) of adjacent molecules enclose an angle of 86.33 (1)°.

The same hydrogen bonds as described above are present in the structure of an ethoxy derivative of the title compound [Lei et al. (2008)], however, slightly undulated layers are formed. Stronger undulation of the layers is observed in the structure of a methyl derivative of the title compound [Liu et al. (2004)], in which the keto group is not involved as acceptor in the intramolecular hydrogen bond, but the hydroxyl group bound to the phenyl ring.

Related literature top

For historical background to aroylhydrazones, see: Savanini et al. (2002); Craliz et al. (1955); Pickart et al. (1983); Offe et al. (1952); Arapov et al. (1987); Ranford et al. (1998). For related structures, see: Liu et al. (2004); Lei et al. (2008). For graph-set analysis of hydrogen-bond networks, see: Bernstein et al. (1995); Etter et al. (1990).

Experimental top

All reagents were commercially available and used as received. A methanol (10 ml) solution of 2-hydroxybenzaldehyde (1.63 mmol) was drop-wise added to a methanol solution (10 ml) of 3-hydroxy-2-naphthohydrazide (1.63 mmol), and the mixture was refluxed for 3 h. Then the solution was evaporated on a steam bath to 5 cm³ and cooled to room temperature. Yellow precipitates of the title compound were separated and filtered off, washed with 5 ml of cooled methanol and then dried in air. X-ray quality crystals of the title compound were obtained from methanol by slow solvent evaporation. Yield: 75%, mp 317 °C.

Computing details top

Data collection: COLLECT (Hooft, 2004); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labels and anisotropic displacement ellipsoids (drawn at 50% probability level) for non-H atoms.
	Fig. 2. Hydrogen bonding in the title compound viewed along [0 - 1 0]. The green and red dashed arrows indicate intramolecular N–H···O and O–H···N hydrogen bonds, respectively. The blue dashed arrows indicate intermolecular O–H···O hydrogen bonds leading to strands along [100].
	Fig. 3. Projection of the hydrogen-bond linked chains viewed along [100]. For clarity only the two chains with their axis located within the unit cell are shown. Dashed lines indicate the a glide planes perpendicular to the b-axis.

(E)-3-Hydroxy-N'-(2-hydroxybenzylidene)-2-naphthohydrazide top

Crystal data top

C₁₈H₁₄N₂O₃	F(000) = 640
M_r = 306.32	D_x = 1.422 (1) Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 5508 reflections
a = 12.6749 (4) Å	θ = 3.1–27.5°
b = 4.9666 (1) Å	µ = 0.10 mm⁻¹
c = 22.7299 (6) Å	T = 200 K
V = 1430.87 (7) Å³	Rod, yellow
Z = 4	0.50 × 0.10 × 0.09 mm

Data collection top

Nonius KappaCCD diffractometer	1416 reflections with I > 2σ(I)
Radiation source: rotating anode	R_int = 0.054
MONTEL, graded multilayered X-ray optics monochromator	θ_max = 27.4°, θ_min = 3.3°
Detector resolution: 9 pixels mm^-1	h = −16→16
CCD; rotation images; thick slices, phi/ω–scan	k = −6→6
10328 measured reflections	l = −29→29
1676 independent 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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ²(F_o²) + (0.052P)² + 0.1709P] where P = (F_o² + 2F_c²)/3
1676 reflections	(Δ/σ)_max < 0.001
220 parameters	Δρ_max = 0.16 e Å⁻³
1 restraint	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₈H₁₄N₂O₃	V = 1430.87 (7) Å³
M_r = 306.32	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 12.6749 (4) Å	µ = 0.10 mm⁻¹
b = 4.9666 (1) Å	T = 200 K
c = 22.7299 (6) Å	0.50 × 0.10 × 0.09 mm

Data collection top

Nonius KappaCCD diffractometer	1416 reflections with I > 2σ(I)
10328 measured reflections	R_int = 0.054
1676 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	1 restraint
wR(F²) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	Δρ_max = 0.16 e Å⁻³
1676 reflections	Δρ_min = −0.17 e Å⁻³
220 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > 2σ(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
O1	0.23226 (13)	0.2694 (4)	0.22862 (9)	0.0383 (4)
O2	0.31563 (16)	−0.3045 (5)	0.09755 (11)	0.0533 (6)
H2	0.280 (4)	−0.182 (9)	0.124 (2)	0.092 (14)*
O3	−0.08649 (14)	0.4024 (3)	0.18929 (8)	0.0325 (4)
H3	−0.151 (3)	0.377 (6)	0.1953 (15)	0.044 (8)*
N1	0.09013 (15)	0.1311 (4)	0.17680 (9)	0.0283 (4)
H1	0.019 (2)	0.157 (5)	0.1723 (13)	0.037 (7)*
N2	0.14658 (15)	−0.0532 (4)	0.14425 (8)	0.0290 (4)
C1	0.13752 (17)	0.2878 (5)	0.21681 (10)	0.0258 (5)
C2	0.06987 (17)	0.4915 (5)	0.24682 (10)	0.0250 (5)
C3	−0.03790 (17)	0.5489 (5)	0.23284 (10)	0.0255 (5)
C4	−0.09057 (18)	0.7497 (5)	0.26178 (11)	0.0283 (5)
H4	−0.1612	0.7897	0.2509	0.034*
C5	−0.04258 (17)	0.8986 (5)	0.30734 (10)	0.0272 (5)
C6	−0.0956 (2)	1.1070 (5)	0.33832 (11)	0.0332 (6)
H6	−0.1660	1.1524	0.3280	0.040*
C7	−0.0461 (2)	1.2432 (5)	0.38286 (11)	0.0353 (6)
H7	−0.0828	1.3807	0.4035	0.042*
C8	0.0589 (2)	1.1808 (6)	0.39843 (12)	0.0380 (6)
H8	0.0925	1.2761	0.4294	0.046*
C9	0.1119 (2)	0.9845 (5)	0.36906 (11)	0.0344 (6)
H9	0.1827	0.9443	0.3797	0.041*
C10	0.06327 (18)	0.8391 (5)	0.32300 (10)	0.0279 (5)
C11	0.11661 (18)	0.6368 (5)	0.29118 (11)	0.0282 (5)
H11	0.1880	0.5994	0.3008	0.034*
C12	0.0899 (2)	−0.1961 (5)	0.10947 (11)	0.0301 (5)
H12	0.0156	−0.1697	0.1093	0.036*
C13	0.1346 (2)	−0.3955 (5)	0.07051 (10)	0.0310 (5)
C14	0.2435 (2)	−0.4434 (6)	0.06574 (12)	0.0372 (6)
C15	0.2796 (2)	−0.6364 (7)	0.02599 (16)	0.0501 (7)
H15	0.3532	−0.6656	0.0216	0.060*
C16	0.2097 (3)	−0.7845 (6)	−0.00686 (14)	0.0488 (8)
H16	0.2356	−0.9187	−0.0329	0.059*
C17	0.1027 (3)	−0.7416 (5)	−0.00265 (13)	0.0450 (7)
H17	0.0548	−0.8429	−0.0259	0.054*
C18	0.0665 (2)	−0.5492 (5)	0.03591 (11)	0.0388 (6)
H18	−0.0073	−0.5201	0.0391	0.047*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0226 (8)	0.0433 (10)	0.0489 (10)	0.0037 (7)	−0.0027 (8)	−0.0084 (9)
O2	0.0286 (10)	0.0615 (14)	0.0697 (15)	0.0054 (9)	−0.0018 (10)	−0.0210 (12)
O3	0.0207 (8)	0.0394 (10)	0.0373 (10)	−0.0008 (7)	−0.0018 (7)	−0.0050 (8)
N1	0.0209 (9)	0.0316 (10)	0.0324 (10)	0.0024 (8)	0.0015 (8)	−0.0025 (8)
N2	0.0265 (9)	0.0297 (10)	0.0309 (10)	0.0024 (8)	0.0038 (8)	0.0004 (8)
C1	0.0216 (10)	0.0267 (11)	0.0290 (12)	0.0000 (9)	0.0025 (9)	0.0035 (10)
C2	0.0218 (11)	0.0243 (12)	0.0288 (11)	−0.0016 (9)	0.0026 (9)	0.0038 (9)
C3	0.0228 (11)	0.0268 (11)	0.0270 (11)	−0.0034 (9)	−0.0004 (9)	0.0021 (10)
C4	0.0213 (10)	0.0295 (12)	0.0340 (12)	0.0016 (9)	0.0003 (9)	0.0056 (10)
C5	0.0266 (11)	0.0260 (12)	0.0292 (11)	−0.0020 (9)	0.0012 (9)	0.0044 (9)
C6	0.0321 (12)	0.0314 (13)	0.0362 (14)	0.0010 (10)	0.0045 (10)	0.0029 (11)
C7	0.0439 (14)	0.0290 (13)	0.0330 (13)	0.0009 (11)	0.0056 (11)	−0.0026 (11)
C8	0.0447 (15)	0.0367 (14)	0.0326 (13)	−0.0053 (12)	−0.0032 (12)	−0.0016 (11)
C9	0.0341 (12)	0.0335 (13)	0.0357 (13)	−0.0029 (10)	−0.0065 (11)	0.0020 (11)
C10	0.0289 (12)	0.0263 (12)	0.0285 (12)	−0.0030 (10)	−0.0008 (10)	0.0036 (10)
C11	0.0238 (11)	0.0293 (12)	0.0315 (12)	−0.0007 (9)	−0.0016 (9)	0.0023 (10)
C12	0.0270 (11)	0.0311 (13)	0.0320 (11)	0.0009 (10)	0.0028 (10)	0.0020 (11)
C13	0.0338 (12)	0.0287 (13)	0.0305 (13)	0.0016 (9)	0.0028 (10)	0.0023 (10)
C14	0.0335 (12)	0.0361 (15)	0.0419 (14)	0.0007 (10)	0.0018 (11)	−0.0029 (12)
C15	0.0440 (16)	0.0484 (17)	0.0577 (17)	0.0120 (13)	0.0099 (15)	−0.0050 (15)
C16	0.072 (2)	0.0361 (15)	0.0389 (15)	0.0052 (14)	0.0104 (14)	−0.0061 (13)
C17	0.062 (2)	0.0370 (15)	0.0365 (15)	−0.0039 (14)	−0.0021 (13)	−0.0023 (13)
C18	0.0411 (14)	0.0380 (15)	0.0372 (13)	−0.0031 (11)	−0.0018 (12)	−0.0019 (12)

Geometric parameters (Å, º) top

O1—C1	1.234 (3)	C7—H7	0.9500
O2—C14	1.354 (3)	C8—C9	1.360 (4)
O2—H2	0.96 (5)	C8—H8	0.9500
O3—C3	1.374 (3)	C9—C10	1.413 (3)
O3—H3	0.84 (4)	C9—H9	0.9500
N1—C1	1.339 (3)	C10—C11	1.411 (3)
N1—N2	1.378 (3)	C11—H11	0.9500
N1—H1	0.92 (3)	C12—C13	1.444 (3)
N2—C12	1.283 (3)	C12—H12	0.9500
C1—C2	1.491 (3)	C13—C18	1.395 (3)
C2—C11	1.374 (3)	C13—C14	1.405 (3)
C2—C3	1.431 (3)	C14—C15	1.394 (4)
C3—C4	1.368 (3)	C15—C16	1.372 (5)
C4—C5	1.410 (3)	C15—H15	0.9500
C4—H4	0.9500	C16—C17	1.377 (5)
C5—C10	1.419 (3)	C16—H16	0.9500
C5—C6	1.421 (3)	C17—C18	1.375 (4)
C6—C7	1.369 (4)	C17—H17	0.9500
C6—H6	0.9500	C18—H18	0.9500
C7—C8	1.411 (4)

C14—O2—H2	110 (3)	C8—C9—C10	121.0 (2)
C3—O3—H3	114 (2)	C8—C9—H9	119.5
C1—N1—N2	121.20 (19)	C10—C9—H9	119.5
C1—N1—H1	115.9 (18)	C11—C10—C9	122.3 (2)
N2—N1—H1	122.9 (18)	C11—C10—C5	118.2 (2)
C12—N2—N1	114.05 (19)	C9—C10—C5	119.5 (2)
O1—C1—N1	122.8 (2)	C2—C11—C10	122.9 (2)
O1—C1—C2	120.7 (2)	C2—C11—H11	118.5
N1—C1—C2	116.55 (19)	C10—C11—H11	118.5
C11—C2—C3	118.0 (2)	N2—C12—C13	122.5 (2)
C11—C2—C1	116.35 (19)	N2—C12—H12	118.8
C3—C2—C1	125.6 (2)	C13—C12—H12	118.8
C4—C3—O3	120.88 (19)	C18—C13—C14	118.1 (2)
C4—C3—C2	120.3 (2)	C18—C13—C12	118.6 (2)
O3—C3—C2	118.84 (19)	C14—C13—C12	123.3 (2)
C3—C4—C5	121.6 (2)	O2—C14—C15	118.4 (2)
C3—C4—H4	119.2	O2—C14—C13	122.4 (2)
C5—C4—H4	119.2	C15—C14—C13	119.2 (3)
C4—C5—C10	118.9 (2)	C16—C15—C14	120.7 (3)
C4—C5—C6	122.8 (2)	C16—C15—H15	119.7
C10—C5—C6	118.3 (2)	C14—C15—H15	119.7
C7—C6—C5	120.7 (2)	C15—C16—C17	121.0 (3)
C7—C6—H6	119.7	C15—C16—H16	119.5
C5—C6—H6	119.7	C17—C16—H16	119.5
C6—C7—C8	120.6 (2)	C18—C17—C16	118.7 (3)
C6—C7—H7	119.7	C18—C17—H17	120.6
C8—C7—H7	119.7	C16—C17—H17	120.6
C9—C8—C7	120.0 (2)	C17—C18—C13	122.2 (3)
C9—C8—H8	120.0	C17—C18—H18	118.9
C7—C8—H8	120.0	C13—C18—H18	118.9

C1—N1—N2—C12	177.3 (2)	C4—C5—C10—C11	1.4 (3)
N2—N1—C1—O1	−3.1 (3)	C6—C5—C10—C11	−178.4 (2)
N2—N1—C1—C2	176.38 (18)	C4—C5—C10—C9	−179.2 (2)
O1—C1—C2—C11	−5.6 (3)	C6—C5—C10—C9	1.0 (3)
N1—C1—C2—C11	174.9 (2)	C3—C2—C11—C10	−0.3 (3)
O1—C1—C2—C3	173.6 (2)	C1—C2—C11—C10	179.0 (2)
N1—C1—C2—C3	−5.9 (3)	C9—C10—C11—C2	179.1 (2)
C11—C2—C3—C4	2.3 (3)	C5—C10—C11—C2	−1.5 (3)
C1—C2—C3—C4	−177.0 (2)	N1—N2—C12—C13	178.3 (2)
C11—C2—C3—O3	−178.9 (2)	N2—C12—C13—C18	177.4 (2)
C1—C2—C3—O3	1.8 (3)	N2—C12—C13—C14	−2.4 (4)
O3—C3—C4—C5	178.8 (2)	C18—C13—C14—O2	−179.9 (3)
C2—C3—C4—C5	−2.4 (4)	C12—C13—C14—O2	−0.1 (4)
C3—C4—C5—C10	0.5 (3)	C18—C13—C14—C15	1.5 (4)
C3—C4—C5—C6	−179.7 (2)	C12—C13—C14—C15	−178.7 (3)
C4—C5—C6—C7	179.0 (2)	O2—C14—C15—C16	179.3 (3)
C10—C5—C6—C7	−1.2 (3)	C13—C14—C15—C16	−2.1 (5)
C5—C6—C7—C8	0.7 (4)	C14—C15—C16—C17	1.8 (5)
C6—C7—C8—C9	0.1 (4)	C15—C16—C17—C18	−0.9 (4)
C7—C8—C9—C10	−0.3 (4)	C16—C17—C18—C13	0.4 (4)
C8—C9—C10—C11	179.1 (2)	C14—C13—C18—C17	−0.7 (4)
C8—C9—C10—C5	−0.2 (4)	C12—C13—C18—C17	179.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N2	0.96 (5)	1.87 (5)	2.697 (3)	142 (4)
O3—H3···O1ⁱ	0.84 (4)	1.81 (4)	2.609 (2)	157 (3)
N1—H1···O3	0.92 (3)	1.85 (3)	2.628 (3)	141 (2)

Symmetry code: (i) x−1/2, −y+1/2, z.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₄N₂O₃
M_r	306.32
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	200
a, b, c (Å)	12.6749 (4), 4.9666 (1), 22.7299 (6)
V (Å³)	1430.87 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.50 × 0.10 × 0.09

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	10328, 1676, 1416
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.648

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.095, 1.09
No. of reflections	1676
No. of parameters	220
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.17

Computer programs: COLLECT (Hooft, 2004), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N2	0.96 (5)	1.87 (5)	2.697 (3)	142 (4)
O3—H3···O1ⁱ	0.84 (4)	1.81 (4)	2.609 (2)	157 (3)
N1—H1···O3	0.92 (3)	1.85 (3)	2.628 (3)	141 (2)

Symmetry code: (i) x−1/2, −y+1/2, z.

Acknowledgements

The authors are grateful to Zanjan University, the Faculty of Chemistry and Biochemistry of the LMU Munich, and the School of Chemistry for financial support.

References

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