A chiral photochromic Schiff base: (R)-4-meth­oxy-2-[(1-phenyl­ethyl)imino­meth­yl]phenol

Miura, Y.; Aritake, Y.; Akitsu, T.

doi:10.1107/S1600536809035557

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2381

doi:10.1107/S1600536809035557

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A chiral photochromic Schiff base: (R)-4-methoxy-2-[(1-phenylethyl)iminomethyl]phenol

Yukie Miura,^a Yoshikazu Aritake ^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 28 August 2009; accepted 3 September 2009; online 9 September 2009)

The title chiral photochromic Schiff base compound, C₁₆H₁₇NO₂, was synthesized from (R)-1-phenylethylamine and 5-methoxysalicylaldehyde. The molecule of the title compound exists in the phenol–imine tautomeric form. The dihedral angle between the two aromatic rings is 62.61 (11)°. An intramolecular O—H⋯N hydrogen bond with an O⋯N distance of 2.589 (2) Å is observed. The crystal packing is stabilized by C—H⋯π interactions involving the aromatic ring.

Related literature

For chiral metal complexes and their hybrid materials, see: Akitsu (2007 ); Akitsu & Einaga (2004 , 2005a ,b , 2006a ); Akitsu et al. (2009 ); Yamada (1999 ). For structral comparison of the 1-phenylethylamine moiety, see: Antonov et al. (1995 ); Liu et al. (1997 ). For related Schiff base ligands and their functions, see: Akitsu et al. (2004 ); Akitsu & Einaga (2006b ); Hadjoudis et al. (1987 , 2004 ); Santoni & Rehder (2004 ); Sliwa et al. (2005 ).

Experimental

Crystal data

C₁₆H₁₇NO₂
M_r = 255.31
Monoclinic, P 2₁
a = 8.270 (4) Å
b = 5.886 (3) Å
c = 13.920 (7) Å
β = 93.254 (7)°
V = 676.4 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.21 × 0.19 × 0.07 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ) T_min = 0.983, T_max = 0.994
3805 measured reflections
1677 independent reflections
1454 reflections with I > 2σ(I)
R_int = 0.074

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.088
S = 0.99
1677 reflections
240 parameters
1 restraint
All H-atom parameters refined
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.97 (3)	1.72 (5)	2.589 (2)	151 (3)
C12—H12⋯Cg1ⁱ	1.03 (4)	2.72 (3)	3.536 (3)	137 (3)
C16—H16C⋯Cg1ⁱⁱ	0.98 (4)	2.71 (3)	3.563 (3)	149 (3)
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+1]$ ; (ii) $[-x, y-{\script{1\over 2}}, -z]$ . Cg 1 is the centroid of the C10–C15 ring.

Data collection: SMART (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: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809035557/ci2897sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809035557/ci2897Isup2.hkl

checkCIF report

Comment top

Because of structural flexibility and their application for switching materials and so on, Schiff base compounds are one of the most extensively used ligands in the field of coordination chemistry (Yamada, 1999). Especially, aiming at multifunctional chiral materials, we have investigated Schiff base Cu^II, Ni^II, or Zn^II complexes in view of thermally induced structural phase transition in the solid state (Akitsu & Einaga, 2004), structural change by occlusion of solvents (Akitsu & Einaga, 2005a), chiral conformational change in a solution induced by a photochromic solute (Akitsu & Einaga, 2005b,2006a; Akitsu, 2007), and novel induced CD to achiral metallodendrimers (Akitsu et al., 2009). On the other hand, free Schiff base ligands (Akitsu et al., 2004, Akitsu & Einaga, 2006b) have been also studied as multifunctional components, for example photochromic and thermochromic or fluorescence materials (Hadjoudis et al., 2004) and nonlinear optical materials (Sliwa et al., 2005) and so on. In order to clarify the role of electron-donating methoxy group, as free ligands for tautomerism and photochromism (Hadjoudis et al., 1987), crystal structure of the title compound, (I), has been determined.

Crystal structure of (I) is similar to those of the analogous derivatives (Santoni & Rehder, 2004; Akitsu & Einaga, 2006b). Molecule of (I) (Fig. 1) adopts an E configuration with respect to the imine C═N double bond with a C6—C7—N1—C8 torsion angle of -179.40 (18)°. Thus, the π-conjugate system around the imine group is essentially planar. The C1—O1 bond distance of 1.361 (3) Å suggests that it is in the phenol-imine tautomer. The contraction of the C7═N1 bond [1.283 (3) Å] is also in agreement with the phenol-imine tautomer. As for the methoxy group, the O2—C4 and O2—C16 bond distaces are 1.374 (3) and 1.422 (3) Å, respectively, and the C4—O2—C16 bond angle is 116.9 (2)°. Beside them, geometric parameters reported here agree with corresponding values reported for analogous Schiff base compounds containing the 1-phenylethylamine group (Antonov et al., 1995; Liu et al., 1997). The planarity of (I) is stabilized by an intramolecular O—H···N hydrogen bond (Table 1). However, there is no intermolecular hydrogen bonds associated with the methoxy group. The crystal packing is stabilized by C—H···π interactions involving the C10-C15 ring.

Related literature top

For related literature, see: Akitsu (2007); Akitsu & Einaga (2004, 2005a,b, 2006a,b); Akitsu et al. (2004, 2009); Antonov et al. (1995); Hadjoudis et al. (1987, 2004); Liu et al. (1997); Santoni & Rehder (2004); Sliwa et al. (2005); Yamada (1999).

Experimental top

Treatment of equimolar R-1-phenylethylamine and 5-methoxysalicylaldehyde in methanol at 298 K overnight gave rise to a yellow-green compound (I). Prismatic crystals of (I) were grown from the resulting solution over a period of several days (yield 39.0%). Analysis found: C 73.98, H 6.49, N 5.37%; calculated for C₁₆H₁₇NO₂: C 75.27, H 6.71, N, 5.49%. (precipitates containing non-stoichiometric cystalline water) m.p. 371 K. IR (Nujol, ν, cm^-1): 1632 (imine band). UV-VIS (diffuse reflectance, nm): 255, 329, 470s h.

Computing details top

Data collection: SMART (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: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.

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

Crystal data top

C₁₆H₁₇NO₂	F(000) = 272
M_r = 255.31	D_x = 1.253 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1657 reflections
a = 8.270 (4) Å	θ = 2.5–27.5°
b = 5.886 (3) Å	µ = 0.08 mm⁻¹
c = 13.920 (7) Å	T = 100 K
β = 93.254 (7)°	Plate, yellow
V = 676.4 (6) Å³	0.21 × 0.19 × 0.07 mm
Z = 2

Data collection top

Brruker SMART CCD area-detector diffractometer	1677 independent reflections
Radiation source: fine-focus sealed tube	1454 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.074
Detector resolution: 8.333 pixels mm^-1	θ_max = 27.5°, θ_min = 1.5°
ϕ and ω scans	h = −10→8
Absorption correction: multi-scan (SADABS; Bruker, 1998)	k = −7→7
T_min = 0.983, T_max = 0.994	l = −17→16
3805 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.088	All H-atom parameters refined
S = 0.99	w = 1/[σ²(F_o²) + (0.038P)²] where P = (F_o² + 2F_c²)/3
1677 reflections	(Δ/σ)_max = 0.001
240 parameters	Δρ_max = 0.31 e Å⁻³
1 restraint	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₆H₁₇NO₂	V = 676.4 (6) Å³
M_r = 255.31	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 8.270 (4) Å	µ = 0.08 mm⁻¹
b = 5.886 (3) Å	T = 100 K
c = 13.920 (7) Å	0.21 × 0.19 × 0.07 mm
β = 93.254 (7)°

Data collection top

Brruker SMART CCD area-detector diffractometer	1677 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	1454 reflections with I > 2σ(I)
T_min = 0.983, T_max = 0.994	R_int = 0.074
3805 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	1 restraint
wR(F²) = 0.088	All H-atom parameters refined
S = 0.99	Δρ_max = 0.31 e Å⁻³
1677 reflections	Δρ_min = −0.18 e Å⁻³
240 parameters

Special details top

Experimental. 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 > 2sigma(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.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	−0.10235 (18)	0.3421 (3)	0.24677 (11)	0.0246 (4)
O2	−0.34502 (18)	0.0560 (3)	−0.11019 (11)	0.0236 (4)
N1	0.0495 (2)	−0.0409 (3)	0.26781 (13)	0.0209 (4)
C1	−0.1599 (2)	0.2610 (4)	0.15989 (16)	0.0204 (5)
C2	−0.2717 (3)	0.3907 (4)	0.10592 (17)	0.0235 (5)
C3	−0.3316 (2)	0.3147 (4)	0.01743 (17)	0.0214 (5)
C4	−0.2782 (2)	0.1095 (4)	−0.02039 (15)	0.0202 (5)
C5	−0.1684 (3)	−0.0231 (4)	0.03255 (16)	0.0200 (5)
C6	−0.1087 (2)	0.0500 (4)	0.12470 (15)	0.0190 (5)
C7	0.0002 (2)	−0.0964 (4)	0.18197 (16)	0.0198 (5)
C8	0.1607 (3)	−0.1916 (4)	0.32334 (16)	0.0204 (5)
C9	0.0764 (3)	−0.2731 (5)	0.41192 (19)	0.0253 (6)
C10	0.3138 (2)	−0.0565 (4)	0.34822 (15)	0.0200 (5)
C15	0.4606 (3)	−0.1240 (5)	0.31292 (16)	0.0237 (5)
C14	0.5988 (3)	0.0075 (5)	0.32986 (17)	0.0265 (6)
C13	0.5917 (3)	0.2063 (5)	0.38184 (17)	0.0269 (6)
C12	0.4471 (3)	0.2741 (5)	0.41913 (16)	0.0251 (5)
C11	0.3098 (3)	0.1428 (4)	0.40203 (16)	0.0224 (5)
C16	−0.3038 (3)	−0.1589 (5)	−0.14857 (18)	0.0255 (6)
H1	−0.041 (3)	0.216 (6)	0.2758 (19)	0.044 (9)*
H2	−0.307 (3)	0.526 (5)	0.1294 (16)	0.020 (6)*
H3	−0.408 (3)	0.398 (5)	−0.0179 (16)	0.024 (6)*
H5	−0.129 (3)	−0.164 (4)	0.0095 (14)	0.013 (6)*
H7	0.039 (3)	−0.236 (5)	0.1538 (15)	0.021 (6)*
H8	0.186 (3)	−0.326 (5)	0.2845 (16)	0.022 (6)*
H15	0.466 (3)	−0.261 (5)	0.2753 (19)	0.036 (8)*
H14	0.701 (3)	−0.044 (5)	0.3014 (16)	0.030 (7)*
H13	0.684 (3)	0.319 (6)	0.390 (2)	0.046 (8)*
H12	0.443 (3)	0.421 (5)	0.4568 (16)	0.028 (7)*
H11	0.210 (3)	0.198 (5)	0.4247 (16)	0.029 (6)*
H9A	0.045 (3)	−0.149 (5)	0.4484 (17)	0.031 (7)*
H16A	−0.330 (3)	−0.274 (5)	−0.1053 (18)	0.031 (7)*
H9B	−0.020 (3)	−0.371 (5)	0.3935 (16)	0.026 (6)*
H16B	−0.191 (3)	−0.172 (4)	−0.1610 (14)	0.014 (5)*
H9C	0.147 (3)	−0.381 (6)	0.4531 (19)	0.043 (8)*
H16C	−0.365 (3)	−0.172 (5)	−0.2090 (18)	0.027 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0236 (8)	0.0249 (10)	0.0252 (9)	−0.0010 (8)	0.0002 (7)	−0.0063 (8)
O2	0.0230 (8)	0.0276 (10)	0.0198 (8)	0.0002 (7)	−0.0012 (6)	0.0021 (8)
N1	0.0171 (8)	0.0238 (11)	0.0218 (10)	−0.0012 (8)	0.0011 (7)	−0.0013 (9)
C1	0.0191 (10)	0.0217 (14)	0.0208 (12)	−0.0029 (10)	0.0046 (9)	−0.0015 (10)
C2	0.0208 (10)	0.0195 (13)	0.0306 (13)	0.0001 (10)	0.0055 (9)	−0.0011 (12)
C3	0.0144 (10)	0.0230 (13)	0.0268 (13)	0.0015 (9)	0.0023 (9)	0.0066 (11)
C4	0.0174 (10)	0.0251 (14)	0.0184 (12)	−0.0031 (9)	0.0035 (9)	0.0022 (10)
C5	0.0173 (10)	0.0210 (13)	0.0219 (12)	−0.0021 (9)	0.0033 (8)	−0.0003 (10)
C6	0.0160 (9)	0.0203 (12)	0.0209 (11)	−0.0021 (9)	0.0031 (9)	0.0001 (10)
C7	0.0155 (9)	0.0230 (13)	0.0212 (12)	−0.0017 (9)	0.0043 (8)	0.0002 (10)
C8	0.0202 (10)	0.0194 (12)	0.0215 (12)	0.0014 (9)	0.0002 (9)	−0.0014 (10)
C9	0.0233 (11)	0.0265 (14)	0.0263 (13)	−0.0046 (11)	0.0019 (10)	0.0000 (11)
C10	0.0219 (10)	0.0228 (13)	0.0149 (11)	−0.0009 (10)	−0.0015 (8)	0.0034 (10)
C15	0.0234 (11)	0.0286 (14)	0.0193 (12)	0.0033 (10)	0.0024 (9)	0.0005 (11)
C14	0.0213 (11)	0.0342 (16)	0.0242 (13)	0.0011 (10)	0.0042 (9)	0.0044 (11)
C13	0.0258 (12)	0.0322 (15)	0.0224 (13)	−0.0081 (11)	−0.0012 (10)	0.0043 (11)
C12	0.0302 (12)	0.0255 (14)	0.0192 (12)	−0.0041 (11)	−0.0014 (9)	0.0002 (11)
C11	0.0219 (11)	0.0233 (13)	0.0219 (12)	0.0021 (10)	0.0011 (9)	0.0000 (10)
C16	0.0269 (12)	0.0280 (15)	0.0217 (14)	0.0011 (11)	0.0011 (10)	−0.0009 (12)

Geometric parameters (Å, º) top

O1—C1	1.361 (3)	C8—H8	0.99 (3)
O1—H1	0.98 (3)	C9—H9A	0.93 (3)
O2—C4	1.374 (3)	C9—H9B	1.00 (3)
O2—C16	1.422 (3)	C9—H9C	1.02 (3)
N1—C7	1.283 (3)	C10—C15	1.393 (3)
N1—C8	1.466 (3)	C10—C11	1.393 (3)
C1—C2	1.387 (3)	C15—C14	1.390 (4)
C1—C6	1.409 (3)	C15—H15	0.96 (3)
C2—C3	1.376 (3)	C14—C13	1.379 (4)
C2—H2	0.91 (3)	C14—H14	1.00 (2)
C3—C4	1.399 (3)	C13—C12	1.389 (3)
C3—H3	0.92 (3)	C13—H13	1.01 (3)
C4—C5	1.379 (3)	C12—C11	1.383 (3)
C5—C6	1.415 (3)	C12—H12	1.01 (3)
C5—H5	0.95 (2)	C11—H11	0.95 (3)
C6—C7	1.452 (3)	C16—H16A	0.94 (3)
C7—H7	0.97 (3)	C16—H16B	0.96 (2)
C8—C10	1.519 (3)	C16—H16C	0.96 (3)
C8—C9	1.528 (3)

C1—O1—H1	104.5 (17)	C8—C9—H9A	110.3 (16)
C4—O2—C16	116.9 (2)	C8—C9—H9B	111.4 (13)
C7—N1—C8	119.6 (2)	H9A—C9—H9B	111 (2)
O1—C1—C2	118.5 (2)	C8—C9—H9C	112.1 (14)
O1—C1—C6	121.4 (2)	H9A—C9—H9C	110 (2)
C2—C1—C6	120.1 (2)	H9B—C9—H9C	102 (2)
C3—C2—C1	120.0 (2)	C15—C10—C11	118.5 (2)
C3—C2—H2	119.8 (16)	C15—C10—C8	120.2 (2)
C1—C2—H2	120.2 (16)	C11—C10—C8	121.22 (19)
C2—C3—C4	120.8 (2)	C14—C15—C10	120.4 (2)
C2—C3—H3	120.4 (16)	C14—C15—H15	119.8 (16)
C4—C3—H3	118.8 (16)	C10—C15—H15	119.8 (16)
O2—C4—C5	125.1 (2)	C13—C14—C15	120.2 (2)
O2—C4—C3	114.9 (2)	C13—C14—H14	121.9 (17)
C5—C4—C3	120.0 (2)	C15—C14—H14	117.9 (17)
C4—C5—C6	119.9 (2)	C14—C13—C12	120.2 (2)
C4—C5—H5	122.7 (14)	C14—C13—H13	124.3 (17)
C6—C5—H5	117.4 (14)	C12—C13—H13	115.3 (18)
C1—C6—C5	119.1 (2)	C11—C12—C13	119.4 (2)
C1—C6—C7	121.4 (2)	C11—C12—H12	121.2 (14)
C5—C6—C7	119.4 (2)	C13—C12—H12	119.4 (14)
N1—C7—C6	121.0 (2)	C12—C11—C10	121.2 (2)
N1—C7—H7	119.8 (14)	C12—C11—H11	117.8 (17)
C6—C7—H7	119.2 (14)	C10—C11—H11	120.8 (17)
N1—C8—C10	107.1 (2)	O2—C16—H16A	109.4 (17)
N1—C8—C9	108.32 (18)	O2—C16—H16B	113.2 (14)
C10—C8—C9	113.1 (2)	H16A—C16—H16B	109 (2)
N1—C8—H8	110.1 (14)	O2—C16—H16C	106.1 (17)
C10—C8—H8	110.1 (14)	H16A—C16—H16C	112 (2)
C9—C8—H8	108.1 (14)	H16B—C16—H16C	107.6 (18)

O1—C1—C2—C3	179.53 (18)	C1—C6—C7—N1	2.0 (3)
C6—C1—C2—C3	−0.6 (3)	C5—C6—C7—N1	−176.18 (18)
C1—C2—C3—C4	−1.6 (3)	C7—N1—C8—C10	120.2 (2)
C16—O2—C4—C5	3.7 (3)	C7—N1—C8—C9	−117.5 (2)
C16—O2—C4—C3	−175.42 (18)	N1—C8—C10—C15	−116.8 (2)
C2—C3—C4—O2	−178.62 (18)	C9—C8—C10—C15	124.0 (2)
C2—C3—C4—C5	2.2 (3)	N1—C8—C10—C11	59.8 (3)
O2—C4—C5—C6	−179.69 (17)	C9—C8—C10—C11	−59.5 (3)
C3—C4—C5—C6	−0.6 (3)	C11—C10—C15—C14	−1.1 (3)
O1—C1—C6—C5	−177.98 (17)	C8—C10—C15—C14	175.5 (2)
C2—C1—C6—C5	2.2 (3)	C10—C15—C14—C13	0.0 (4)
O1—C1—C6—C7	3.8 (3)	C15—C14—C13—C12	1.2 (4)
C2—C1—C6—C7	−176.03 (19)	C14—C13—C12—C11	−1.3 (4)
C4—C5—C6—C1	−1.5 (3)	C13—C12—C11—C10	0.1 (4)
C4—C5—C6—C7	176.70 (19)	C15—C10—C11—C12	1.1 (3)
C8—N1—C7—C6	−179.40 (18)	C8—C10—C11—C12	−175.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.97 (3)	1.72 (5)	2.589 (2)	151 (3)
C12—H12···Cg1ⁱ	1.03 (4)	2.72 (3)	3.536 (3)	137 (3)
C16—H16C···Cg1ⁱⁱ	0.98 (4)	2.71 (3)	3.563 (3)	149 (3)

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₇NO₂
M_r	255.31
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	100
a, b, c (Å)	8.270 (4), 5.886 (3), 13.920 (7)
β (°)	93.254 (7)
V (Å³)	676.4 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.21 × 0.19 × 0.07

Data collection
Diffractometer	Brruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.983, 0.994
No. of measured, independent and observed [I > 2σ(I)] reflections	3805, 1677, 1454
R_int	0.074
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.088, 0.99
No. of reflections	1677
No. of parameters	240
No. of restraints	1
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.18

Computer programs: SMART (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	0.97 (3)	1.72 (5)	2.589 (2)	151 (3)
C12—H12···Cg1ⁱ	1.03 (4)	2.72 (3)	3.536 (3)	137 (3)
C16—H16C···Cg1ⁱⁱ	0.98 (4)	2.71 (3)	3.563 (3)	149 (3)

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

Acknowledgements

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

References

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Volume 65| Part 10| October 2009| Page o2381

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

A chiral photochromic Schiff base: (R)-4-meth­­oxy-2-[(1-phenyl­ethyl)imino­meth­yl]phenol

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

A chiral photochromic Schiff base: (R)-4-methoxy-2-[(1-phenylethyl)iminomethyl]phenol