(E)-4-Allyl-2-[(2-hydroxy-phen-yl)iminiometh-yl]-6-methoxy-phenolate.

The title compound, C(17)H(17)NO(3), crystallizes in a zwitterionic form with cationic iminium and anionic enolate groups. The zwitterion exists in a trans configuration about the C=N bond. The dihedral angle between the two benzene rings is 13.42 (7)°. The meth-oxy group is almost coplanar [C-O-C-C = 2.1 (2)°] with the attached ring whereas the allyl unit is oriented at a dihedral angle of 67.9 (1)°. An intra-molecular N-H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, the mol-ecules are linked into zigzag chains along [010] by O-H⋯O hydrogen bonds. In addition, weak C-H⋯π inter-actions are observed.

Related literature

For background to Schiff bases and their applications, see: Dao et al. (2000 ▶); Eltayeb & Ahmed (2005a ▶,b ▶); Karthikeyan et al. (2006 ▶); Sriram et al. (2006 ▶). For related structures, see: Eltayeb et al. (2009 ▶); Tan & Liu (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C17H17NO3

M = 283.32

Orthorhombic,

a = 14.719 (3) Å

b = 9.1302 (16) Å

c = 20.597 (4) Å

V = 2768.0 (9) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.50 × 0.15 × 0.02 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.955, T max = 0.998

16563 measured reflections

4056 independent reflections

2744 reflections with I > 2σ(I)

R int = 0.073

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.141

S = 1.00

4056 reflections

254 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.39 e Å−3

Δρmin = −0.29 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681000838X/ci5052sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681000838X/ci5052Isup2.hkl

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

C17H17NO3	F(000) = 1200
Mr = 283.32	Dx = 1.360 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4056 reflections
a = 14.719 (3) Å	θ = 2.0–30.2°
b = 9.1302 (16) Å	µ = 0.09 mm−1
c = 20.597 (4) Å	T = 100 K
V = 2768.0 (9) Å3	Plate, red
Z = 8	0.50 × 0.15 × 0.02 mm

Bruker APEX DUO CCD area-detector diffractometer	4056 independent reflections
Radiation source: sealed tube	2744 reflections with I > 2σ(I)
graphite	Rint = 0.073
φ and ω scans	θmax = 30.2°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −20→20
Tmin = 0.955, Tmax = 0.998	k = −12→12
16563 measured reflections	l = −26→28

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0776P)2] where P = (Fo2 + 2Fc2)/3
4056 reflections	(Δ/σ)max = 0.001
254 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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 > 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.

	x	y	z	Uiso*/Ueq
O1	0.01450 (7)	0.45448 (12)	0.30069 (5)	0.0161 (2)
H1O1	−0.0369	0.3930	0.3044	0.024*
O2	0.12030 (7)	0.76365 (12)	0.20618 (6)	0.0180 (3)
O3	0.15126 (7)	0.93837 (13)	0.10464 (5)	0.0197 (3)
N1	0.18381 (8)	0.56151 (14)	0.28699 (6)	0.0135 (3)
C1	0.07946 (9)	0.39626 (16)	0.33947 (7)	0.0135 (3)
C2	0.06178 (10)	0.28421 (18)	0.38347 (8)	0.0167 (3)
C3	0.13112 (11)	0.22677 (18)	0.42119 (8)	0.0186 (3)
C4	0.21898 (11)	0.28105 (18)	0.41570 (8)	0.0177 (3)
C5	0.23708 (10)	0.39363 (17)	0.37262 (8)	0.0153 (3)
C6	0.16809 (10)	0.45100 (16)	0.33395 (7)	0.0136 (3)
C7	0.26375 (10)	0.60410 (17)	0.26593 (7)	0.0145 (3)
C8	0.27799 (9)	0.71113 (16)	0.21797 (7)	0.0133 (3)
C9	0.36954 (10)	0.74371 (17)	0.20005 (8)	0.0150 (3)
C10	0.38828 (10)	0.84469 (17)	0.15316 (8)	0.0166 (3)
C11	0.31474 (11)	0.91227 (17)	0.12006 (8)	0.0166 (3)
C12	0.22584 (10)	0.88183 (16)	0.13544 (8)	0.0147 (3)
C13	0.20324 (10)	0.78420 (16)	0.18785 (7)	0.0139 (3)
C14	0.16825 (13)	1.03310 (19)	0.05078 (9)	0.0221 (4)
C15	0.48556 (11)	0.8797 (2)	0.13422 (9)	0.0207 (4)
C16	0.52342 (10)	0.77196 (19)	0.08627 (8)	0.0188 (3)
C17	0.55487 (11)	0.8048 (2)	0.02828 (9)	0.0244 (4)
H2	0.0021 (12)	0.247 (2)	0.3859 (8)	0.015 (4)*
H3	0.1195 (13)	0.144 (2)	0.4528 (9)	0.025 (5)*
H4	0.2678 (14)	0.238 (2)	0.4435 (10)	0.031 (5)*
H5	0.2969 (13)	0.435 (2)	0.3707 (9)	0.023 (5)*
H7	0.3152 (12)	0.5554 (19)	0.2862 (8)	0.015 (4)*
H9	0.4179 (13)	0.6900 (19)	0.2254 (8)	0.019 (5)*
H11	0.3273 (13)	0.983 (2)	0.0852 (9)	0.024 (5)*
H14A	0.1109 (14)	1.062 (2)	0.0335 (10)	0.030 (5)*
H14B	0.2011 (14)	1.124 (2)	0.0651 (10)	0.034 (6)*
H14C	0.2072 (13)	0.985 (2)	0.0176 (9)	0.025 (5)*
H15A	0.5199 (14)	0.882 (2)	0.1754 (10)	0.032 (6)*
H15C	0.4901 (12)	0.982 (2)	0.1163 (9)	0.015 (4)*
H16	0.5258 (13)	0.672 (2)	0.1013 (9)	0.029 (5)*
H17A	0.5552 (14)	0.909 (2)	0.0120 (10)	0.033 (5)*
H17B	0.5755 (15)	0.729 (2)	−0.0016 (10)	0.038 (6)*
H1N1	0.1343 (15)	0.611 (2)	0.2647 (10)	0.035 (6)*

	U11	U22	U33	U12	U13	U23
O1	0.0080 (5)	0.0182 (6)	0.0222 (6)	−0.0005 (4)	−0.0012 (4)	0.0024 (5)
O2	0.0091 (5)	0.0203 (6)	0.0246 (6)	0.0008 (4)	0.0019 (4)	0.0038 (5)
O3	0.0153 (5)	0.0214 (6)	0.0223 (6)	0.0032 (4)	−0.0001 (4)	0.0063 (5)
N1	0.0101 (6)	0.0140 (6)	0.0164 (7)	−0.0008 (5)	−0.0003 (5)	0.0008 (5)
C1	0.0091 (6)	0.0140 (7)	0.0173 (8)	0.0023 (5)	−0.0004 (5)	−0.0023 (6)
C2	0.0127 (7)	0.0170 (8)	0.0204 (8)	−0.0020 (6)	0.0014 (6)	0.0011 (6)
C3	0.0170 (7)	0.0177 (8)	0.0211 (8)	0.0006 (6)	0.0012 (6)	0.0030 (6)
C4	0.0155 (7)	0.0180 (8)	0.0196 (8)	0.0018 (6)	−0.0026 (6)	0.0004 (6)
C5	0.0106 (6)	0.0174 (8)	0.0178 (8)	−0.0006 (5)	−0.0019 (5)	−0.0006 (6)
C6	0.0118 (6)	0.0128 (7)	0.0162 (8)	−0.0006 (5)	0.0015 (5)	−0.0007 (6)
C7	0.0100 (6)	0.0150 (7)	0.0186 (8)	0.0003 (5)	−0.0006 (5)	−0.0020 (6)
C8	0.0104 (6)	0.0133 (7)	0.0164 (8)	−0.0013 (5)	0.0011 (5)	−0.0024 (6)
C9	0.0104 (6)	0.0148 (7)	0.0198 (8)	−0.0018 (5)	0.0006 (5)	−0.0016 (6)
C10	0.0124 (7)	0.0160 (7)	0.0213 (8)	−0.0035 (6)	0.0031 (6)	−0.0040 (6)
C11	0.0179 (7)	0.0139 (7)	0.0181 (8)	−0.0019 (6)	0.0034 (6)	−0.0008 (6)
C12	0.0139 (7)	0.0128 (7)	0.0175 (8)	0.0012 (5)	0.0007 (5)	−0.0007 (6)
C13	0.0109 (7)	0.0128 (7)	0.0181 (8)	−0.0003 (5)	0.0014 (5)	−0.0024 (6)
C14	0.0270 (9)	0.0183 (8)	0.0212 (9)	0.0041 (7)	−0.0001 (7)	0.0047 (7)
C15	0.0136 (7)	0.0254 (9)	0.0230 (9)	−0.0066 (6)	0.0031 (6)	−0.0021 (7)
C16	0.0098 (6)	0.0199 (8)	0.0268 (9)	0.0020 (6)	−0.0003 (6)	0.0013 (7)
C17	0.0148 (8)	0.0326 (10)	0.0259 (9)	0.0016 (7)	0.0002 (6)	−0.0065 (8)

O1—C1	1.3546 (17)	C8—C13	1.428 (2)
O1—H1O1	0.9454	C8—C9	1.4285 (19)
O2—C13	1.2915 (17)	C9—C10	1.363 (2)
O3—C12	1.3691 (18)	C9—H9	1.010 (18)
O3—C14	1.429 (2)	C10—C11	1.420 (2)
N1—C7	1.3129 (19)	C10—C15	1.518 (2)
N1—C6	1.4168 (19)	C11—C12	1.375 (2)
N1—H1N1	0.97 (2)	C11—H11	0.982 (19)
C1—C2	1.391 (2)	C12—C13	1.439 (2)
C1—C6	1.4015 (19)	C14—H14A	0.95 (2)
C2—C3	1.386 (2)	C14—H14B	1.01 (2)
C2—H2	0.944 (18)	C14—H14C	0.99 (2)
C3—C4	1.390 (2)	C15—C16	1.501 (2)
C3—H3	1.010 (19)	C15—H15A	0.99 (2)
C4—C5	1.384 (2)	C15—H15C	1.003 (19)
C4—H4	1.00 (2)	C16—C17	1.316 (2)
C5—C6	1.393 (2)	C16—H16	0.96 (2)
C5—H5	0.960 (19)	C17—H17A	1.01 (2)
C7—C8	1.405 (2)	C17—H17B	0.98 (2)
C7—H7	0.972 (18)
C1—O1—H1O1	106.5	C8—C9—H9	115.5 (10)
C12—O3—C14	116.60 (12)	C9—C10—C11	118.66 (14)
C7—N1—C6	125.65 (13)	C9—C10—C15	121.01 (14)
C7—N1—H1N1	112.1 (13)	C11—C10—C15	120.27 (15)
C6—N1—H1N1	122.2 (13)	C12—C11—C10	121.80 (15)
O1—C1—C2	122.72 (13)	C12—C11—H11	118.7 (12)
O1—C1—C6	117.99 (13)	C10—C11—H11	119.5 (12)
C2—C1—C6	119.29 (13)	O3—C12—C11	125.46 (14)
C3—C2—C1	120.38 (14)	O3—C12—C13	113.32 (13)
C3—C2—H2	121.2 (11)	C11—C12—C13	121.22 (14)
C1—C2—H2	118.4 (11)	O2—C13—C8	122.23 (14)
C2—C3—C4	120.32 (15)	O2—C13—C12	121.86 (13)
C2—C3—H3	121.3 (11)	C8—C13—C12	115.91 (13)
C4—C3—H3	118.4 (11)	O3—C14—H14A	107.5 (12)
C5—C4—C3	119.76 (14)	O3—C14—H14B	110.9 (12)
C5—C4—H4	121.5 (12)	H14A—C14—H14B	108.0 (17)
C3—C4—H4	118.7 (12)	O3—C14—H14C	111.6 (11)
C4—C5—C6	120.37 (14)	H14A—C14—H14C	111.9 (16)
C4—C5—H5	119.9 (12)	H14B—C14—H14C	106.9 (16)
C6—C5—H5	119.7 (12)	C16—C15—C10	112.41 (13)
C5—C6—C1	119.88 (14)	C16—C15—H15A	113.0 (12)
C5—C6—N1	122.62 (13)	C10—C15—H15A	105.5 (12)
C1—C6—N1	117.48 (13)	C16—C15—H15C	109.9 (10)
N1—C7—C8	124.88 (14)	C10—C15—H15C	110.7 (10)
N1—C7—H7	114.9 (10)	H15A—C15—H15C	105.0 (16)
C8—C7—H7	120.2 (10)	C17—C16—C15	125.35 (17)
C7—C8—C13	121.01 (13)	C17—C16—H16	119.6 (12)
C7—C8—C9	117.85 (13)	C15—C16—H16	115.0 (12)
C13—C8—C9	121.15 (14)	C16—C17—H17A	121.2 (12)
C10—C9—C8	120.97 (14)	C16—C17—H17B	121.3 (12)
C10—C9—H9	123.5 (10)	H17A—C17—H17B	117.4 (17)
O1—C1—C2—C3	178.84 (14)	C8—C9—C10—C15	179.82 (14)
C6—C1—C2—C3	−0.3 (2)	C9—C10—C11—C12	2.0 (2)
C1—C2—C3—C4	0.3 (2)	C15—C10—C11—C12	179.24 (15)
C2—C3—C4—C5	0.4 (2)	C14—O3—C12—C11	2.1 (2)
C3—C4—C5—C6	−1.1 (2)	C14—O3—C12—C13	−178.25 (13)
C4—C5—C6—C1	1.1 (2)	C10—C11—C12—O3	−177.77 (14)
C4—C5—C6—N1	−177.01 (14)	C10—C11—C12—C13	2.6 (2)
O1—C1—C6—C5	−179.60 (14)	C7—C8—C13—O2	5.1 (2)
C2—C1—C6—C5	−0.4 (2)	C9—C8—C13—O2	−175.35 (14)
O1—C1—C6—N1	−1.4 (2)	C7—C8—C13—C12	−174.61 (14)
C2—C1—C6—N1	177.85 (13)	C9—C8—C13—C12	5.0 (2)
C7—N1—C6—C5	12.8 (2)	O3—C12—C13—O2	−5.3 (2)
C7—N1—C6—C1	−165.40 (14)	C11—C12—C13—O2	174.39 (14)
C6—N1—C7—C8	178.13 (14)	O3—C12—C13—C8	174.40 (12)
N1—C7—C8—C13	0.3 (2)	C11—C12—C13—C8	−5.9 (2)
N1—C7—C8—C9	−179.33 (14)	C9—C10—C15—C16	82.87 (19)
C7—C8—C9—C10	178.97 (14)	C11—C10—C15—C16	−94.28 (18)
C13—C8—C9—C10	−0.6 (2)	C10—C15—C16—C17	121.37 (18)
C8—C9—C10—C11	−3.0 (2)

Cg1 is the centroid of the C8–C13 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O2i	0.95	1.72	2.6443 (16)	166
O1—H1O1···O3i	0.95	2.55	3.1268 (16)	119
N1—H1N1···O2	0.97 (2)	1.85 (2)	2.6553 (18)	138 (2)
C14—H14B···Cg1ii	1.01 (2)	2.75 (2)	3.569 (2)	139 (2)

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C8–C13 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯O2i	0.95	1.72	2.6443 (16)	166
O1—H1O1⋯O3i	0.95	2.55	3.1268 (16)	119
N1—H1N1⋯O2	0.97 (2)	1.85 (2)	2.6553 (18)	138 (2)
C14—H14B⋯Cg1ii	1.01 (2)	2.75 (2)	3.569 (2)	139 (2)

Symmetry codes: (i) ; (ii) .