(E)-4-Hy-droxy-2-{[(2-phenyl-eth-yl)iminium-yl]meth-yl}phenolate.

The title Schiff base compound, C(15)H(15)NO(2), crystallized as the iminium-phenolate zwitterion. The H atom is localized on the imine N atom, forming a strong intra-molecular hydrogen bond with the phenolate O atom, and giving rise to an S(6) ring motif. The mol-ecule has an E conformation about the C=N bond. In the crystal, mol-ecules are linked by O-H⋯O hydrogen bonds, forming chains propagating along [010]. There are also C-H⋯O inter-actions present.

Related literature

For general background to the characteristics of Schiff bases, see: Krause et al. (1995 ▶); Hadjoudis et al. (2004 ▶). For related structures, see: Dominiak et al. (2006 ▶); Santos-Contreras et al. (2009 ▶); Ng (2008 ▶). For n class="Chemical">hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C15H15NO2

M = 241.28

Monoclinic,

a = 9.5010 (19) Å

b = 12.936 (3) Å

c = 12.551 (4) Å

β = 124.81 (2)°

V = 1266.5 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 170 K

0.50 × 0.20 × 0.20 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: for a sphere(Dwiggins, 1975 ▶) T min = 0.861, T max = 0.862

15718 measured reflections

2773 independent reflections

2367 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.107

S = 1.02

2773 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.22 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: HKL SCALEPACK (Otwinowski & Minor 1997 ▶); data reduction: HKL DENZO/SCALEPACK (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812025408/su2447sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812025408/su2447Isup2.hkl

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

C15H15NO2	F(000) = 512
Mr = 241.28	Dx = 1.265 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 14042 reflections
a = 9.5010 (19) Å	θ = 2.9–27.5°
b = 12.936 (3) Å	µ = 0.08 mm−1
c = 12.551 (4) Å	T = 170 K
β = 124.81 (2)°	Prism, orange
V = 1266.5 (6) Å3	0.50 × 0.20 × 0.20 mm
Z = 4

Nonius KappaCCD diffractometer	2773 independent reflections
Radiation source: Enraf Nonius FR590	2367 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
Detector resolution: 9 pixels mm-1	θmax = 27.5°, θmin = 4.1°
CCD rotation images, thick slices scans	h = −10→12
Absorption correction: for a sphere (Dwiggins, 1975)	k = −16→16
Tmin = 0.861, Tmax = 0.862	l = −13→13
15718 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0502P)2 + 0.3688P] where P = (Fo2 + 2Fc2)/3
2773 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

Experimental. Spectroscopic data for the title compound: FT—IR by ATR (cm-1): 1643 (C═ N as intense band), 1496 (Asymmetrical C=C—O···H stretch), 3311 (free phenolic O—H intense broad band), 3059 (intramolecular hydrogen bonding N—H···O, as a weak broad band). LC/MS/TOF on HPLC-methanol solution, m/z (%) calculated: 242.1181 (100); found 242.1175 (100) [M+H]+, molecular formula C15H15NO2. 1H NMR (CDCl3, 300.1MHz): δ 6.83 (m, H5 and H6), 6.67 (s, H3), 8.12 (s, H7), 3.84 (t, H9), 3.00 (t, H10), 7.19–7.32 (m, H12—H16). 13C NMR (CDCl3, 75.4MHz): δ 147.5 (C1), 118.4 (C2), 116.6 (C3), 144.0 (C4), 119.9 (C5), 117.6 (C6), 164.5 (C7), 61.1 (C9), 37.3 (C10), 139.3 (C11), 128.9 (C13, C15), 128.5 (C12, C16), 126.4 (C14).

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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.

	x	y	z	Uiso*/Ueq
O1	0.88467 (11)	0.43206 (6)	0.61806 (8)	0.0320 (3)
O4	0.99566 (15)	0.00918 (7)	0.64559 (9)	0.0460 (3)
N8	0.75925 (13)	0.42202 (8)	0.37321 (9)	0.0284 (3)
C1	0.90916 (14)	0.33115 (8)	0.62390 (11)	0.0245 (3)
C2	0.85954 (14)	0.27185 (8)	0.51050 (10)	0.0241 (3)
C3	0.88858 (15)	0.16354 (9)	0.51983 (11)	0.0272 (3)
C4	0.96636 (16)	0.11344 (9)	0.63837 (11)	0.0290 (3)
C5	1.01496 (15)	0.17148 (9)	0.75028 (11)	0.0288 (3)
C6	0.98611 (15)	0.27637 (9)	0.74326 (11)	0.0276 (3)
C7	0.78312 (14)	0.32274 (9)	0.38709 (11)	0.0256 (3)
C9	0.68816 (16)	0.47659 (9)	0.24949 (12)	0.0325 (4)
C10	0.52322 (16)	0.53653 (10)	0.20739 (13)	0.0364 (4)
C11	0.55332 (15)	0.62068 (9)	0.30222 (11)	0.0314 (3)
C12	0.48187 (17)	0.61459 (12)	0.37397 (13)	0.0408 (4)
C13	0.51032 (18)	0.69276 (14)	0.46060 (14)	0.0495 (5)
C14	0.60966 (18)	0.77808 (13)	0.47683 (14)	0.0470 (5)
C15	0.68349 (17)	0.78487 (10)	0.40787 (13)	0.0399 (4)
C16	0.65511 (16)	0.70707 (10)	0.32130 (12)	0.0332 (4)
H3	0.85445	0.12504	0.44421	0.0326*
H4	1.03190	−0.01141	0.71879	0.0689*
H5	1.06841	0.13740	0.83162	0.0345*
H6	1.01819	0.31299	0.81963	0.0332*
H7	0.74885	0.28207	0.31297	0.0307*
H8	0.78653	0.45796	0.44009	0.0341*
H9A	0.66198	0.42590	0.18137	0.0389*
H9B	0.77472	0.52552	0.25890	0.0389*
H10A	0.47519	0.56802	0.12123	0.0437*
H10B	0.43734	0.48727	0.19847	0.0437*
H12	0.41353	0.55663	0.36330	0.0490*
H13	0.46162	0.68769	0.50873	0.0594*
H14	0.62724	0.83176	0.53491	0.0565*
H15	0.75308	0.84257	0.42000	0.0479*
H16	0.70530	0.71235	0.27424	0.0398*

	U11	U22	U33	U12	U13	U23
O1	0.0424 (5)	0.0208 (4)	0.0295 (4)	0.0003 (3)	0.0185 (4)	−0.0023 (3)
O4	0.0827 (8)	0.0218 (4)	0.0385 (5)	0.0085 (5)	0.0376 (5)	0.0045 (4)
N8	0.0316 (5)	0.0272 (5)	0.0248 (5)	0.0016 (4)	0.0151 (4)	0.0004 (4)
C1	0.0234 (5)	0.0229 (5)	0.0270 (6)	−0.0020 (4)	0.0142 (5)	−0.0025 (4)
C2	0.0230 (5)	0.0248 (6)	0.0249 (6)	−0.0016 (4)	0.0140 (5)	−0.0007 (4)
C3	0.0324 (6)	0.0245 (6)	0.0272 (6)	−0.0024 (4)	0.0185 (5)	−0.0041 (4)
C4	0.0374 (6)	0.0209 (5)	0.0327 (6)	0.0000 (5)	0.0223 (5)	−0.0001 (4)
C5	0.0340 (6)	0.0269 (6)	0.0260 (6)	−0.0001 (5)	0.0175 (5)	0.0025 (4)
C6	0.0309 (6)	0.0266 (6)	0.0242 (6)	−0.0024 (5)	0.0150 (5)	−0.0034 (4)
C7	0.0250 (5)	0.0266 (6)	0.0262 (6)	−0.0006 (4)	0.0152 (5)	−0.0022 (4)
C9	0.0375 (7)	0.0311 (6)	0.0282 (6)	0.0038 (5)	0.0184 (5)	0.0049 (5)
C10	0.0318 (6)	0.0347 (7)	0.0327 (7)	0.0034 (5)	0.0125 (5)	0.0044 (5)
C11	0.0253 (6)	0.0348 (6)	0.0299 (6)	0.0077 (5)	0.0132 (5)	0.0087 (5)
C12	0.0288 (6)	0.0540 (8)	0.0385 (7)	0.0031 (6)	0.0185 (6)	0.0116 (6)
C13	0.0347 (7)	0.0833 (12)	0.0348 (7)	0.0142 (7)	0.0224 (6)	0.0074 (7)
C14	0.0340 (7)	0.0616 (10)	0.0349 (8)	0.0144 (7)	0.0134 (6)	−0.0054 (6)
C15	0.0324 (7)	0.0371 (7)	0.0403 (7)	0.0061 (5)	0.0149 (6)	0.0020 (5)
C16	0.0312 (6)	0.0356 (7)	0.0342 (7)	0.0058 (5)	0.0195 (5)	0.0065 (5)

O1—C1	1.3206 (14)	C12—C13	1.394 (2)
O4—C4	1.3696 (16)	C13—C14	1.390 (3)
O4—H4	0.8200	C14—C15	1.394 (3)
N8—C7	1.2985 (16)	C15—C16	1.3898 (19)
N8—C9	1.4725 (16)	C3—H3	0.9500
N8—H8	0.8600	C5—H5	0.9500
C1—C6	1.4250 (17)	C6—H6	0.9500
C1—C2	1.4389 (16)	C7—H7	0.9500
C2—C7	1.4407 (16)	C9—H9A	0.9900
C2—C3	1.4199 (16)	C9—H9B	0.9900
C3—C4	1.3872 (17)	C10—H10A	0.9900
C4—C5	1.4175 (17)	C10—H10B	0.9900
C5—C6	1.3771 (17)	C12—H12	0.9500
C9—C10	1.546 (2)	C13—H13	0.9500
C10—C11	1.5148 (19)	C14—H14	0.9500
C11—C16	1.406 (2)	C15—H15	0.9500
C11—C12	1.406 (2)	C16—H16	0.9500
C4—O4—H4	109.00	C4—C3—H3	120.00
C7—N8—C9	123.74 (10)	C4—C5—H5	119.00
C9—N8—H8	118.00	C6—C5—H5	119.00
C7—N8—H8	118.00	C1—C6—H6	119.00
O1—C1—C2	121.62 (10)	C5—C6—H6	119.00
O1—C1—C6	121.22 (10)	N8—C7—H7	119.00
C2—C1—C6	117.17 (10)	C2—C7—H7	119.00
C1—C2—C7	119.95 (10)	N8—C9—H9A	109.00
C1—C2—C3	120.40 (10)	N8—C9—H9B	109.00
C3—C2—C7	119.64 (10)	C10—C9—H9A	109.00
C2—C3—C4	120.59 (11)	C10—C9—H9B	109.00
O4—C4—C3	119.65 (11)	H9A—C9—H9B	108.00
C3—C4—C5	119.21 (11)	C9—C10—H10A	109.00
O4—C4—C5	121.14 (10)	C9—C10—H10B	109.00
C4—C5—C6	121.21 (11)	C11—C10—H10A	109.00
C1—C6—C5	121.41 (11)	C11—C10—H10B	109.00
N8—C7—C2	122.58 (11)	H10A—C10—H10B	108.00
N8—C9—C10	111.47 (13)	C11—C12—H12	120.00
C9—C10—C11	113.07 (12)	C13—C12—H12	120.00
C10—C11—C12	121.30 (13)	C12—C13—H13	120.00
C10—C11—C16	120.53 (14)	C14—C13—H13	120.00
C12—C11—C16	118.18 (12)	C13—C14—H14	120.00
C11—C12—C13	120.64 (15)	C15—C14—H14	120.00
C12—C13—C14	120.24 (17)	C14—C15—H15	120.00
C13—C14—C15	119.97 (15)	C16—C15—H15	120.00
C14—C15—C16	119.87 (15)	C11—C16—H16	119.00
C11—C16—C15	121.08 (15)	C15—C16—H16	119.00
C2—C3—H3	120.00
C9—N8—C7—C2	177.35 (15)	O4—C4—C5—C6	179.78 (16)
C7—N8—C9—C10	121.46 (15)	C3—C4—C5—C6	0.1 (3)
C6—C1—C2—C3	−0.5 (2)	C4—C5—C6—C1	−1.1 (2)
C6—C1—C2—C7	−179.18 (14)	N8—C9—C10—C11	62.54 (15)
O1—C1—C6—C5	−178.71 (15)	C9—C10—C11—C12	−113.64 (16)
C2—C1—C6—C5	1.3 (2)	C9—C10—C11—C16	65.94 (16)
O1—C1—C2—C7	0.8 (2)	C10—C11—C12—C13	−179.82 (14)
O1—C1—C2—C3	179.54 (14)	C16—C11—C12—C13	0.6 (2)
C7—C2—C3—C4	178.19 (15)	C10—C11—C16—C15	179.90 (13)
C1—C2—C3—C4	−0.5 (2)	C12—C11—C16—C15	−0.5 (2)
C3—C2—C7—N8	−177.33 (15)	C11—C12—C13—C14	0.2 (2)
C1—C2—C7—N8	1.4 (2)	C12—C13—C14—C15	−1.0 (2)
C2—C3—C4—C5	0.7 (2)	C13—C14—C15—C16	1.1 (2)
C2—C3—C4—O4	−178.96 (15)	C14—C15—C16—C11	−0.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N8—H8···O1	0.86	1.90	2.5884 (15)	137
O4—H4···O1i	0.82	1.87	2.6902 (15)	176
C6—H6···O4ii	0.95	2.59	3.2818 (18)	130

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N8—H8⋯O1	0.86	1.90	2.5884 (15)	137
O4—H4⋯O1i	0.82	1.87	2.6902 (15)	176
C6—H6⋯O4ii	0.95	2.59	3.2818 (18)	130

Symmetry codes: (i) ; (ii) .