A chiral photochromic Schiff base: (R)-4-meth-oxy-2-[(1-phenyl-ethyl)imino-meth-yl]phenol.

The title chiral photochromic Schiff base compound, C(16)H(17)NO(2), was synthesized from (R)-1-phenyl-ethyl-amine and 5-methoxy-salicylaldehyde. The mol-ecule of the title compound exists in the phenol-imine tautomeric form. The dihedral angle between the two aromatic rings is 62.61 (11)°. An intra-molecular 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 inter-actions 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 = 255.31

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.088

S = 0.99

1677 reflections

240 parameters

1 restraint

All H-atom parameters refined

Δρmax = 0.31 e Å−3

Δρmin = −0.18 e Å−3

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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Enhanced figure: interactive version of Fig. 1

C16H17NO2	F(000) = 272
Mr = 255.31	Dx = 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

Brruker SMART CCD area-detector diffractometer	1677 independent reflections
Radiation source: fine-focus sealed tube	1454 reflections with I > 2σ(I)
graphite	Rint = 0.074
Detector resolution: 8.333 pixels mm-1	θmax = 27.5°, θmin = 1.5°
φ and ω scans	h = −10→8
Absorption correction: multi-scan (SADABS; Bruker, 1998)	k = −7→7
Tmin = 0.983, Tmax = 0.994	l = −17→16
3805 measured reflections

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(Fo2) + (0.038P)2] where P = (Fo2 + 2Fc2)/3
1677 reflections	(Δ/σ)max = 0.001
240 parameters	Δρmax = 0.31 e Å−3
1 restraint	Δρmin = −0.18 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)*

	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)

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)

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)

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) ; (ii) . Cg 1 is the centroid of the C10–C15 ring.