4-Phenyl­diazenyl-2-[(R)-(1-phenyl­ethyl)imino­meth­yl]phenol

Aritake, Y.; Watanabe, Y.; Akitsu, T.

doi:10.1107/S1600536810007762

organic compounds

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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page o749

doi:10.1107/S1600536810007762

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4-Phenyldiazenyl-2-[(R)-(1-phenylethyl)iminomethyl]phenol

Yoshikazu Aritake,^a Yoshimasa Watanabe ^a and Takashiro Akitsu ^a ^*

^aDepartment of Chemistry, Faculty of Science, Tokyo University of Science, 1-3 Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan
^*Correspondence e-mail: akitsu@rs.kagu.tus.ac.jp

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

The title chiral photochromic Schiff base compound, C₂₁H₁₉N₃O, was synthesized from (R)-1-phenylethylamine and the salicylaldehyde of an azobenzene derivative. The molecule corresponds to the phenol–imine tautomer, the C=N and N—C bond distances being 1.279 (3) and 1.477 (3) Å, respectively. An intramolecular O—H⋯N hydrogen bond occurs. The diazenyl group adopts a trans form with an N=N distance of 1.243 (3) Å.

Related literature

For applications of Schiff base–metal complexes and azobenzene, see: Akitsu & Einaga (2005a ,b ); Akitsu (2007 ); Akitsu & Itoh (2010 ). For Schiff base ligands, see: Akitsu et al. (2004 , 2006 ); Miura et al. (2009 ); Hadjoudis & Mavridis (2004 ). For Schiff base compounds with an azobenzene group, see: Aslantaş et al. (2007 ); Khandar & Rezvani (1999 ).

Experimental

Crystal data

C₂₁H₁₉N₃O
M_r = 329.39
Monoclinic, C 2
a = 22.430 (2) Å
b = 5.9566 (6) Å
c = 13.4670 (13) Å
β = 106.396 (1)°
V = 1726.1 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 173 K
0.31 × 0.12 × 0.09 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.976, T_max = 0.993
4632 measured reflections
1960 independent reflections
1741 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.123
S = 0.96
1960 reflections
231 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	1.01 (4)	1.66 (4)	2.557 (3)	145 (3)

Data collection: APEX2 (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); 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 global, I. DOI: 10.1107/S1600536810007762/zq2030sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810007762/zq2030Isup2.hkl

checkCIF report

Comment top

In the recent years, we have developed organic-inorganic hybrid materials of photochromic compounds and chiral Schiff base metal complexes. Due to structural flexibility of such complexes, cis-trans photoisomerization of azobenzene could switch conformation of chiral ligands (Akitsu & Einaga, 2005a,b). Moreover, multifunctional (photochemical) development of Schiff base Cu^II, Ni^II, or Zn^II complexes (Akitsu, 2007) and optical anisotropy in polymer films (Akitsu & Itoh, 2010) have been reported so far. On the other hand, free Schiff base ligands may act as photochromic, thermochromic, and fluorescence materials (Hadjoudis et al., 2004). We have developed chiral Schiff base liagnds to include chiral functions (Akitsu et al., 2004, 2006b; Miura et al., 2009). Herein we prepared the title chiral photochromic Schiff base compound (I), having two photochromic moieties.

The crystal structure of (I) is similar to that of the analogous Schiff base ligands (Akitsu et al., 2006b; Miura et al., 2009). The molecule of (I) (Fig. 1) adopts an E configuration with respect to the imine C=N double bond with C6—C7—N1—C8 torsion angle of 179.21 (16)°. Thus, the π-conjugated system around the imine group is essentially planar. The C1—O1 bond distance of 1.337 (3) Å suggests that it is in the phenol-imine tautomer. The contraction of the C7=N1 bond is also in agreement with the phenol-imine tautomer. As for the azobenzene moiety, the azo N=N double bond adopts an E configuration with the N=N distance of 1.243 (3) Å. Beside them, geometric parameters reported agree with the corresponding values for analogous azobenzene derivatives (Aslantaş et al., 2007; Khandar & Rezvani,1999).

The planarity of (I) is stabilized by an intramolecular O—H···N hydrogen bond (Table 1). However, there is no intermolecular hydrogen bonds in the crystal structure.

Related literature top

For applications of Schiff base–metal complexes and azobenzene, see: Akitsu & Einaga (2005a,b); Akitsu (2007); Akitsu & Itoh (2010). For Schiff base ligands, see: Akitsu et al. (2004, 2006); Miura et al. (2009); Hadjoudis & Mavridis (2004). For Schiff base compounds with an azobenzene group, see: Aslantaş et al. (2007); Khandar & Rezvani (1999). .

Experimental top

Treatment of aniline (6.24 g, 67.0 mmol) in 30 ml of 6M HCl and NaNO₂ (4.69 g, 68.0 mmol) in 30 ml of H₂O for 30 min at 278 K gave rise to the yellow precursor. Treatment of the precursor and salicylaldehyde (8.18 g, 67.0 mmol) in 30 ml of 10 % NaOH aqueous solution for 1 hour at 278 K, and the resulting brown precipitates were filtrated and washed with water and ethanol, and dried in a desiccator for several days. Treatment of the brown precipitates (0.226 g, 1.00 mmol) and (R)-1-phenylethylamine (0.121 g, 1.00 mmol) for 2 hours at 313 K gave rise to redish violet crystals after evaporation (yield 0.21 g, 64 %).

Computing details top

Data collection: APEX2 (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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 the atom labeling scheme. Displacement ellipsoids are drawn at the 50% probability level.

4-phenyldiazenyl-2-[(R)-(1-phenylethyl)iminomethyl]phenol top

Crystal data top

C₂₁H₁₉N₃O	F(000) = 696
M_r = 329.39	D_x = 1.268 Mg m⁻³
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2y	Cell parameters from 1707 reflections
a = 22.430 (2) Å	θ = 2.8–25.6°
b = 5.9566 (6) Å	µ = 0.08 mm⁻¹
c = 13.4670 (13) Å	T = 173 K
β = 106.396 (1)°	Prism, red violet
V = 1726.1 (3) Å³	0.31 × 0.12 × 0.09 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	1960 independent reflections
Radiation source: fine-focus sealed tube	1741 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
Detector resolution: 8.333 pixels mm^-1	θ_max = 26.6°, θ_min = 1.6°
ϕ and ω scans	h = −16→28
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −6→7
T_min = 0.976, T_max = 0.993	l = −16→16
4632 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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	w = 1/[σ²(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
1960 reflections	(Δ/σ)_max = 0.001
231 parameters	Δρ_max = 0.26 e Å⁻³
1 restraint	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₂₁H₁₉N₃O	V = 1726.1 (3) Å³
M_r = 329.39	Z = 4
Monoclinic, C2	Mo Kα radiation
a = 22.430 (2) Å	µ = 0.08 mm⁻¹
b = 5.9566 (6) Å	T = 173 K
c = 13.4670 (13) Å	0.31 × 0.12 × 0.09 mm
β = 106.396 (1)°

Data collection top

Bruker APEXII CCD diffractometer	1960 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1741 reflections with I > 2σ(I)
T_min = 0.976, T_max = 0.993	R_int = 0.029
4632 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	1 restraint
wR(F²) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	Δρ_max = 0.26 e Å⁻³
1960 reflections	Δρ_min = −0.27 e Å⁻³
231 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
O1	0.99357 (8)	−0.0345 (3)	0.86831 (13)	0.0407 (4)
C5	1.01961 (10)	0.3842 (4)	0.68547 (16)	0.0311 (5)
H5	1.0052	0.5273	0.6577	0.037*
C2	1.06244 (11)	−0.0381 (4)	0.76572 (17)	0.0358 (5)
H2	1.0775	−0.1809	0.7930	0.043*
C6	0.99411 (9)	0.2834 (4)	0.75769 (15)	0.0286 (5)
C4	1.06632 (10)	0.2751 (4)	0.65393 (16)	0.0328 (5)
C3	1.08666 (11)	0.0649 (4)	0.69370 (18)	0.0364 (5)
H3	1.1179	−0.0097	0.6710	0.044*
C17	1.10112 (11)	0.8454 (4)	0.44134 (19)	0.0386 (6)
H17	1.0665	0.9222	0.4526	0.046*
C7	0.94575 (9)	0.3980 (4)	0.79195 (15)	0.0286 (5)
H7	0.9314	0.5415	0.7646	0.034*
C16	1.11935 (10)	0.6407 (4)	0.48836 (16)	0.0326 (5)
C1	1.01590 (10)	0.0684 (4)	0.79815 (16)	0.0301 (5)
C21	1.17050 (11)	0.5300 (4)	0.47323 (18)	0.0382 (6)
H21	1.1831	0.3894	0.5057	0.046*
C18	1.13343 (12)	0.9384 (5)	0.37779 (18)	0.0439 (6)
H18	1.1205	1.0778	0.3444	0.053*
C13	0.72251 (11)	−0.0416 (5)	0.85593 (19)	0.0414 (6)
H13	0.6892	−0.1453	0.8464	0.050*
C10	0.82061 (9)	0.2628 (4)	0.88270 (16)	0.0297 (5)
C8	0.87446 (9)	0.4249 (4)	0.89349 (16)	0.0311 (5)
H8	0.8598	0.5583	0.8481	0.037*
C20	1.20294 (11)	0.6245 (5)	0.41107 (19)	0.0449 (7)
H20	1.2382	0.5495	0.4010	0.054*
C19	1.18438 (11)	0.8291 (5)	0.36290 (18)	0.0451 (7)
H19	1.2068	0.8937	0.3197	0.054*
C11	0.76386 (10)	0.3026 (5)	0.81026 (17)	0.0371 (5)
H11	0.7580	0.4359	0.7699	0.045*
C15	0.82718 (10)	0.0696 (4)	0.94228 (19)	0.0380 (6)
H15	0.8656	0.0397	0.9923	0.046*
C14	0.77806 (11)	−0.0812 (5)	0.9297 (2)	0.0441 (6)
H14	0.7829	−0.2114	0.9720	0.053*
C12	0.71552 (11)	0.1493 (5)	0.79616 (19)	0.0429 (6)
H12	0.6773	0.1764	0.7449	0.051*
C9	0.90390 (11)	0.5033 (5)	1.00386 (17)	0.0393 (6)
H9A	0.9363	0.6144	1.0046	0.059*
H9B	0.9224	0.3746	1.0469	0.059*
H9C	0.8720	0.5714	1.0312	0.059*
N3	1.08366 (9)	0.5577 (3)	0.55470 (14)	0.0347 (5)
N1	0.92269 (8)	0.3059 (3)	0.85861 (14)	0.0320 (4)
N2	1.09774 (9)	0.3622 (3)	0.58460 (15)	0.0375 (5)
H1	0.9594 (15)	0.061 (7)	0.882 (2)	0.075 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0506 (10)	0.0315 (9)	0.0472 (9)	0.0084 (8)	0.0254 (8)	0.0107 (8)
C5	0.0337 (11)	0.0279 (11)	0.0295 (10)	−0.0018 (10)	0.0053 (8)	0.0015 (10)
C2	0.0434 (12)	0.0261 (12)	0.0387 (11)	0.0061 (10)	0.0127 (10)	0.0024 (10)
C6	0.0303 (10)	0.0268 (11)	0.0271 (9)	−0.0028 (10)	0.0053 (8)	−0.0019 (9)
C4	0.0353 (11)	0.0351 (12)	0.0275 (10)	−0.0048 (11)	0.0082 (8)	0.0000 (10)
C3	0.0405 (12)	0.0336 (13)	0.0382 (12)	0.0049 (11)	0.0163 (10)	−0.0010 (10)
C17	0.0388 (12)	0.0350 (14)	0.0396 (11)	−0.0016 (11)	0.0071 (10)	−0.0017 (10)
C7	0.0272 (10)	0.0272 (11)	0.0296 (10)	0.0010 (9)	0.0052 (8)	0.0010 (9)
C16	0.0344 (11)	0.0363 (13)	0.0247 (10)	−0.0067 (10)	0.0045 (8)	−0.0021 (9)
C1	0.0347 (11)	0.0273 (12)	0.0288 (10)	−0.0020 (10)	0.0096 (9)	−0.0010 (9)
C21	0.0404 (12)	0.0343 (13)	0.0381 (11)	0.0001 (10)	0.0081 (10)	0.0027 (11)
C18	0.0491 (14)	0.0378 (14)	0.0388 (12)	−0.0066 (12)	0.0028 (11)	0.0108 (11)
C13	0.0331 (12)	0.0411 (14)	0.0537 (14)	−0.0038 (11)	0.0183 (10)	−0.0094 (12)
C10	0.0293 (10)	0.0315 (12)	0.0289 (10)	0.0045 (9)	0.0091 (8)	−0.0001 (9)
C8	0.0310 (11)	0.0288 (12)	0.0342 (10)	0.0047 (9)	0.0101 (9)	0.0027 (9)
C20	0.0381 (13)	0.0555 (18)	0.0429 (13)	−0.0007 (13)	0.0141 (11)	−0.0023 (13)
C19	0.0448 (14)	0.0546 (17)	0.0343 (11)	−0.0163 (13)	0.0082 (10)	0.0037 (12)
C11	0.0385 (12)	0.0374 (13)	0.0329 (10)	0.0042 (11)	0.0061 (9)	0.0021 (11)
C15	0.0313 (11)	0.0360 (13)	0.0440 (12)	0.0043 (11)	0.0061 (10)	0.0078 (11)
C14	0.0469 (14)	0.0335 (14)	0.0539 (14)	0.0034 (11)	0.0178 (11)	0.0072 (12)
C12	0.0332 (12)	0.0501 (16)	0.0417 (12)	0.0046 (12)	0.0046 (10)	−0.0059 (12)
C9	0.0361 (12)	0.0402 (14)	0.0402 (12)	0.0025 (11)	0.0083 (10)	−0.0053 (11)
N3	0.0364 (10)	0.0347 (11)	0.0315 (9)	0.0028 (9)	0.0069 (8)	0.0002 (9)
N1	0.0299 (9)	0.0304 (10)	0.0353 (9)	0.0037 (9)	0.0087 (7)	0.0002 (8)
N2	0.0441 (11)	0.0332 (11)	0.0362 (10)	0.0017 (9)	0.0128 (9)	0.0005 (9)

Geometric parameters (Å, º) top

O1—C1	1.337 (3)	C18—H18	0.9500
O1—H1	1.01 (4)	C13—C12	1.376 (4)
C5—C4	1.397 (3)	C13—C14	1.377 (4)
C5—C6	1.396 (3)	C13—H13	0.9500
C5—H5	0.9500	C10—C15	1.386 (3)
C2—C3	1.382 (3)	C10—C11	1.388 (3)
C2—C1	1.393 (3)	C10—C8	1.521 (3)
C2—H2	0.9500	C8—N1	1.477 (3)
C6—C1	1.423 (3)	C8—C9	1.520 (3)
C6—C7	1.462 (3)	C8—H8	1.0000
C4—C3	1.387 (3)	C20—C19	1.388 (4)
C4—N2	1.418 (3)	C20—H20	0.9500
C3—H3	0.9500	C19—H19	0.9500
C17—C16	1.382 (3)	C11—C12	1.389 (3)
C17—C18	1.384 (3)	C11—H11	0.9500
C17—H17	0.9500	C15—C14	1.394 (4)
C7—N1	1.279 (3)	C15—H15	0.9500
C7—H7	0.9500	C14—H14	0.9500
C16—C21	1.387 (3)	C12—H12	0.9500
C16—N3	1.445 (3)	C9—H9A	0.9800
C21—C20	1.375 (3)	C9—H9B	0.9800
C21—H21	0.9500	C9—H9C	0.9800
C18—C19	1.378 (4)	N3—N2	1.243 (3)

C1—O1—H1	109 (2)	C15—C10—C11	118.4 (2)
C4—C5—C6	120.1 (2)	C15—C10—C8	121.32 (19)
C4—C5—H5	119.9	C11—C10—C8	120.3 (2)
C6—C5—H5	119.9	N1—C8—C9	107.67 (17)
C3—C2—C1	119.7 (2)	N1—C8—C10	107.34 (18)
C3—C2—H2	120.1	C9—C8—C10	113.74 (18)
C1—C2—H2	120.1	N1—C8—H8	109.3
C5—C6—C1	119.3 (2)	C9—C8—H8	109.3
C5—C6—C7	120.3 (2)	C10—C8—H8	109.3
C1—C6—C7	120.3 (2)	C21—C20—C19	120.2 (2)
C3—C4—C5	119.7 (2)	C21—C20—H20	119.9
C3—C4—N2	114.5 (2)	C19—C20—H20	119.9
C5—C4—N2	125.8 (2)	C18—C19—C20	119.9 (2)
C2—C3—C4	121.3 (2)	C18—C19—H19	120.1
C2—C3—H3	119.3	C20—C19—H19	120.1
C4—C3—H3	119.3	C10—C11—C12	120.6 (2)
C16—C17—C18	119.9 (2)	C10—C11—H11	119.7
C16—C17—H17	120.1	C12—C11—H11	119.7
C18—C17—H17	120.1	C10—C15—C14	120.9 (2)
N1—C7—C6	120.3 (2)	C10—C15—H15	119.6
N1—C7—H7	119.9	C14—C15—H15	119.6
C6—C7—H7	119.9	C13—C14—C15	120.0 (2)
C17—C16—C21	120.2 (2)	C13—C14—H14	120.0
C17—C16—N3	116.2 (2)	C15—C14—H14	120.0
C21—C16—N3	123.6 (2)	C13—C12—C11	120.5 (2)
O1—C1—C2	118.4 (2)	C13—C12—H12	119.8
O1—C1—C6	121.8 (2)	C11—C12—H12	119.8
C2—C1—C6	119.8 (2)	C8—C9—H9A	109.5
C20—C21—C16	119.8 (2)	C8—C9—H9B	109.5
C20—C21—H21	120.1	H9A—C9—H9B	109.5
C16—C21—H21	120.1	C8—C9—H9C	109.5
C19—C18—C17	120.1 (3)	H9A—C9—H9C	109.5
C19—C18—H18	119.9	H9B—C9—H9C	109.5
C17—C18—H18	119.9	N2—N3—C16	112.7 (2)
C12—C13—C14	119.6 (2)	C7—N1—C8	119.7 (2)
C12—C13—H13	120.2	N3—N2—C4	115.3 (2)
C14—C13—H13	120.2

C4—C5—C6—C1	−0.4 (3)	C15—C10—C8—C9	−53.4 (3)
C4—C5—C6—C7	179.25 (17)	C11—C10—C8—C9	128.4 (2)
C6—C5—C4—C3	0.8 (3)	C16—C21—C20—C19	−0.5 (4)
C6—C5—C4—N2	−177.3 (2)	C17—C18—C19—C20	0.6 (4)
C1—C2—C3—C4	1.1 (4)	C21—C20—C19—C18	0.3 (4)
C5—C4—C3—C2	−1.2 (3)	C15—C10—C11—C12	−1.7 (3)
N2—C4—C3—C2	177.2 (2)	C8—C10—C11—C12	176.6 (2)
C5—C6—C7—N1	−179.60 (19)	C11—C10—C15—C14	0.1 (3)
C1—C6—C7—N1	0.0 (3)	C8—C10—C15—C14	−178.1 (2)
C18—C17—C16—C21	1.0 (3)	C12—C13—C14—C15	−1.1 (4)
C18—C17—C16—N3	179.1 (2)	C10—C15—C14—C13	1.3 (4)
C3—C2—C1—O1	−179.6 (2)	C14—C13—C12—C11	−0.5 (4)
C3—C2—C1—C6	−0.6 (3)	C10—C11—C12—C13	1.9 (4)
C5—C6—C1—O1	179.2 (2)	C17—C16—N3—N2	172.05 (19)
C7—C6—C1—O1	−0.4 (3)	C21—C16—N3—N2	−9.9 (3)
C5—C6—C1—C2	0.3 (3)	C6—C7—N1—C8	179.21 (16)
C7—C6—C1—C2	−179.3 (2)	C9—C8—N1—C7	−107.9 (2)
C17—C16—C21—C20	−0.1 (3)	C10—C8—N1—C7	129.3 (2)
N3—C16—C21—C20	−178.1 (2)	C16—N3—N2—C4	177.16 (18)
C16—C17—C18—C19	−1.2 (4)	C3—C4—N2—N3	−174.4 (2)
C15—C10—C8—N1	65.6 (2)	C5—C4—N2—N3	3.8 (3)
C11—C10—C8—N1	−112.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	1.01 (4)	1.66 (4)	2.557 (3)	145 (3)

Experimental details

Crystal data
Chemical formula	C₂₁H₁₉N₃O
M_r	329.39
Crystal system, space group	Monoclinic, C2
Temperature (K)	173
a, b, c (Å)	22.430 (2), 5.9566 (6), 13.4670 (13)
β (°)	106.396 (1)
V (Å³)	1726.1 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.31 × 0.12 × 0.09

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.976, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	4632, 1960, 1741
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.629

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.123, 0.96
No. of reflections	1960
No. of parameters	231
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)	0.26, −0.27

Computer programs: APEX2 (Bruker, 1998), SAINT (Bruker, 1998), 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
O1—H1···N1	1.01 (4)	1.66 (4)	2.557 (3)	145 (3)

Acknowledgements

This work was supported by the Kato Foundation for the Promotion of Science.

References

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