(E)-2-[(2-Ethyl-phen-yl)iminiometh-yl]-6-hydroxy-phenolate.

The mol-ecule of the title compound, C(15)H(15)NO(2), crystallizes in a zwitterionic form, and displays an E configuration about the C=N bond. The dihedral angle between the two aromatic rings is 5.59 (6)°. An intra-molecular N-H⋯O hydrogen bond generates an S(6) ring motif. In the crystal structure, pairs of mol-ecules are linked into centrosymmetric R(2) (2)(10) dimers by pairs of O-H⋯O hydrogen bonds. Aromatic π-π inter-actions are observed between the benzene rings of adjacent dimers [centroid-centroid distance = 3.4808 (7) Å].

Related literature

For the synthesis, structure and properties of Schiff base complexes, see: Lee et al. (2005 ▶); Sriram et al. (2006 ▶); Hao (2009 ▶); Bedia et al. (2006 ▶). For related structures, see: Tüfekçi et al. (2009 ▶); Yazıcı et al. (2010 ▶).

Experimental

Crystal data

C15H15NO2

M = 241.28

Monoclinic,

a = 7.7482 (4) Å

b = 10.8713 (7) Å

c = 15.4742 (7) Å

β = 117.380 (3)°

V = 1157.42 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 150 K

0.77 × 0.63 × 0.39 mm

Data collection

Stoe IPDS II diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.945, T max = 0.967

10088 measured reflections

2655 independent reflections

2384 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.117

S = 1.05

2655 reflections

167 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.39 e Å−3

Δρmin = −0.45 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); 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 (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810002503/ci5022sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810002503/ci5022Isup2.hkl

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

C15H15NO2	F(000) = 512
Mr = 241.28	Dx = 1.385 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 14793 reflections
a = 7.7482 (4) Å	θ = 2.4–28.0°
b = 10.8713 (7) Å	µ = 0.09 mm−1
c = 15.4742 (7) Å	T = 150 K
β = 117.380 (3)°	Prism, red
V = 1157.42 (11) Å3	0.77 × 0.63 × 0.39 mm
Z = 4

Stoe IPDS II diffractometer	2655 independent reflections
Radiation source: fine-focus sealed tube	2384 reflections with I > 2σ(I)
graphite	Rint = 0.047
Detector resolution: 6.67 pixels mm-1	θmax = 27.5°, θmin = 2.4°
ω scan	h = −10→10
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −14→14
Tmin = 0.945, Tmax = 0.967	l = −20→20
10088 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) = 0.117	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0624P)2 + 0.418P] where P = (Fo2 + 2Fc2)/3
2655 reflections	(Δ/σ)max = 0.001
167 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.45 e Å−3

Experimental. 196 frames, detector distance = 80 mm The beam size = 0.8 mm.

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.

	x	y	z	Uiso*/Ueq
C1	0.36021 (16)	0.72765 (10)	0.47504 (8)	0.0173 (2)
C2	0.48396 (17)	0.81367 (10)	0.54271 (8)	0.0183 (2)
C3	0.40045 (18)	0.89865 (11)	0.57970 (9)	0.0220 (3)
H3	0.4791	0.9567	0.6248	0.026*
C4	0.20240 (18)	0.89846 (11)	0.55063 (9)	0.0240 (3)
H4	0.1497	0.9558	0.5764	0.029*
C5	0.08307 (17)	0.81329 (12)	0.48342 (9)	0.0232 (3)
H5	−0.0498	0.8137	0.4639	0.028*
C6	0.16097 (17)	0.72722 (11)	0.44512 (9)	0.0208 (3)
H6	0.0810	0.6698	0.3999	0.025*
C7	0.69934 (17)	0.81261 (11)	0.57319 (9)	0.0221 (3)
H7A	0.7175	0.8322	0.5168	0.026*
H7B	0.7475	0.7297	0.5933	0.026*
C8	0.82267 (19)	0.90037 (13)	0.65481 (10)	0.0300 (3)
H8A	0.9564	0.8927	0.6687	0.045*
H8B	0.8098	0.8806	0.7120	0.045*
H8C	0.7798	0.9833	0.6353	0.045*
C9	0.35682 (16)	0.55612 (10)	0.37159 (8)	0.0182 (2)
H9	0.2228	0.5478	0.3460	0.022*
C10	0.45648 (16)	0.47823 (10)	0.33700 (8)	0.0179 (2)
C11	0.34923 (17)	0.39280 (11)	0.26133 (9)	0.0206 (3)
H11	0.2151	0.3872	0.2367	0.025*
C12	0.44263 (18)	0.31928 (11)	0.22495 (9)	0.0231 (3)
H12	0.3725	0.2634	0.1757	0.028*
C13	0.64667 (18)	0.32805 (11)	0.26231 (9)	0.0225 (3)
H13	0.7088	0.2782	0.2363	0.027*
C14	0.75465 (17)	0.40778 (11)	0.33558 (8)	0.0195 (2)
C15	0.66399 (16)	0.48648 (10)	0.37727 (8)	0.0176 (2)
N1	0.44559 (14)	0.64003 (9)	0.43849 (7)	0.0171 (2)
O1	0.76679 (12)	0.56081 (8)	0.44695 (6)	0.0214 (2)
O2	0.95018 (12)	0.41463 (8)	0.36831 (7)	0.0246 (2)
H2	0.9964	0.4658	0.4120	0.037*
H1	0.578 (3)	0.6363 (18)	0.4597 (13)	0.042 (5)*

	U11	U22	U33	U12	U13	U23
C1	0.0190 (5)	0.0158 (5)	0.0176 (5)	0.0033 (4)	0.0090 (4)	0.0031 (4)
C2	0.0184 (5)	0.0182 (5)	0.0183 (5)	0.0016 (4)	0.0086 (4)	0.0026 (4)
C3	0.0237 (6)	0.0198 (6)	0.0221 (6)	0.0015 (4)	0.0102 (5)	−0.0015 (4)
C4	0.0258 (6)	0.0234 (6)	0.0252 (6)	0.0080 (5)	0.0138 (5)	0.0012 (5)
C5	0.0173 (5)	0.0264 (6)	0.0263 (6)	0.0049 (4)	0.0103 (5)	0.0032 (5)
C6	0.0189 (6)	0.0209 (6)	0.0211 (6)	0.0008 (4)	0.0077 (4)	0.0008 (4)
C7	0.0184 (5)	0.0241 (6)	0.0241 (6)	−0.0003 (4)	0.0102 (5)	−0.0038 (5)
C8	0.0218 (6)	0.0349 (7)	0.0311 (7)	−0.0053 (5)	0.0103 (5)	−0.0099 (6)
C9	0.0166 (5)	0.0177 (5)	0.0178 (5)	0.0004 (4)	0.0058 (4)	0.0028 (4)
C10	0.0193 (5)	0.0158 (5)	0.0165 (5)	0.0008 (4)	0.0066 (4)	0.0016 (4)
C11	0.0190 (5)	0.0193 (5)	0.0192 (6)	−0.0008 (4)	0.0051 (4)	0.0007 (4)
C12	0.0264 (6)	0.0192 (5)	0.0184 (6)	−0.0012 (4)	0.0058 (5)	−0.0031 (4)
C13	0.0271 (6)	0.0198 (5)	0.0201 (6)	0.0045 (4)	0.0105 (5)	−0.0013 (4)
C14	0.0195 (5)	0.0192 (5)	0.0186 (5)	0.0031 (4)	0.0078 (4)	0.0026 (4)
C15	0.0195 (5)	0.0149 (5)	0.0171 (5)	0.0010 (4)	0.0072 (4)	0.0015 (4)
N1	0.0161 (5)	0.0168 (4)	0.0177 (5)	0.0017 (3)	0.0072 (4)	0.0009 (4)
O1	0.0179 (4)	0.0207 (4)	0.0221 (4)	−0.0007 (3)	0.0063 (3)	−0.0054 (3)
O2	0.0190 (4)	0.0297 (5)	0.0238 (4)	0.0026 (3)	0.0087 (3)	−0.0052 (4)

C1—C6	1.3929 (16)	C8—H8C	0.96
C1—C2	1.4025 (16)	C9—N1	1.3122 (15)
C1—N1	1.4174 (14)	C9—C10	1.4071 (16)
C2—C3	1.3930 (16)	C9—H9	0.93
C2—C7	1.5112 (16)	C10—C11	1.4245 (16)
C3—C4	1.3864 (17)	C10—C15	1.4352 (15)
C3—H3	0.93	C11—C12	1.3617 (17)
C4—C5	1.3818 (18)	C11—H11	0.93
C4—H4	0.93	C12—C13	1.4149 (17)
C5—C6	1.3857 (17)	C12—H12	0.93
C5—H5	0.93	C13—C14	1.3654 (17)
C6—H6	0.93	C13—H13	0.93
C7—C8	1.5194 (17)	C14—O2	1.3607 (14)
C7—H7A	0.97	C14—C15	1.4346 (16)
C7—H7B	0.97	C15—O1	1.2885 (14)
C8—H8A	0.96	N1—H1	0.924 (18)
C8—H8B	0.96	O2—H2	0.82
C6—C1—C2	121.54 (10)	H8A—C8—H8C	109.5
C6—C1—N1	120.96 (10)	H8B—C8—H8C	109.5
C2—C1—N1	117.50 (10)	N1—C9—C10	122.56 (10)
C3—C2—C1	117.50 (11)	N1—C9—H9	118.7
C3—C2—C7	122.13 (11)	C10—C9—H9	118.7
C1—C2—C7	120.37 (10)	C9—C10—C11	119.36 (10)
C4—C3—C2	121.31 (11)	C9—C10—C15	119.90 (10)
C4—C3—H3	119.3	C11—C10—C15	120.74 (10)
C2—C3—H3	119.3	C12—C11—C10	120.16 (11)
C5—C4—C3	120.19 (11)	C12—C11—H11	119.9
C5—C4—H4	119.9	C10—C11—H11	119.9
C3—C4—H4	119.9	C11—C12—C13	119.87 (11)
C4—C5—C6	120.14 (11)	C11—C12—H12	120.1
C4—C5—H5	119.9	C13—C12—H12	120.1
C6—C5—H5	119.9	C14—C13—C12	121.66 (11)
C5—C6—C1	119.32 (11)	C14—C13—H13	119.2
C5—C6—H6	120.3	C12—C13—H13	119.2
C1—C6—H6	120.3	O2—C14—C13	119.73 (11)
C2—C7—C8	115.90 (10)	O2—C14—C15	119.44 (10)
C2—C7—H7A	108.3	C13—C14—C15	120.81 (11)
C8—C7—H7A	108.3	O1—C15—C14	120.55 (10)
C2—C7—H7B	108.3	O1—C15—C10	122.71 (10)
C8—C7—H7B	108.3	C14—C15—C10	116.74 (10)
H7A—C7—H7B	107.4	C9—N1—C1	127.62 (10)
C7—C8—H8A	109.5	C9—N1—H1	110.1 (12)
C7—C8—H8B	109.5	C1—N1—H1	122.3 (12)
H8A—C8—H8B	109.5	C14—O2—H2	109.5
C7—C8—H8C	109.5
C6—C1—C2—C3	0.44 (17)	C15—C10—C11—C12	−1.24 (17)
N1—C1—C2—C3	−179.08 (10)	C10—C11—C12—C13	−0.15 (18)
C6—C1—C2—C7	−179.48 (11)	C11—C12—C13—C14	0.92 (19)
N1—C1—C2—C7	0.99 (16)	C12—C13—C14—O2	−178.98 (11)
C1—C2—C3—C4	−0.13 (18)	C12—C13—C14—C15	−0.28 (18)
C7—C2—C3—C4	179.79 (11)	O2—C14—C15—O1	−1.89 (17)
C2—C3—C4—C5	−0.24 (19)	C13—C14—C15—O1	179.41 (11)
C3—C4—C5—C6	0.32 (19)	O2—C14—C15—C10	177.64 (10)
C4—C5—C6—C1	−0.02 (18)	C13—C14—C15—C10	−1.06 (16)
C2—C1—C6—C5	−0.37 (17)	C9—C10—C15—O1	2.05 (17)
N1—C1—C6—C5	179.14 (10)	C11—C10—C15—O1	−178.67 (10)
C3—C2—C7—C8	6.54 (17)	C9—C10—C15—C14	−177.46 (10)
C1—C2—C7—C8	−173.55 (11)	C11—C10—C15—C14	1.81 (16)
N1—C9—C10—C11	−177.37 (10)	C10—C9—N1—C1	176.29 (10)
N1—C9—C10—C15	1.91 (17)	C6—C1—N1—C9	4.29 (18)
C9—C10—C11—C12	178.03 (11)	C2—C1—N1—C9	−176.19 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.92 (2)	1.77 (2)	2.5793 (16)	145 (2)
O2—H2···O1i	0.82	2.13	2.6993 (12)	127

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.92 (2)	1.77 (2)	2.5793 (16)	145 (2)
O2—H2⋯O1i	0.82	2.13	2.6993 (12)	127

Symmetry code: (i) .