Crystal structure of 2-{(E)-[(2-hy-droxy-phen-yl)iminium-yl]meth-yl}-4-methyl-phenolate.

The title compound, C14H13NO2, exists as a zwitterion in the solid state, with the H atom of the phenol group transferred to the imine N atom. The dihedral angle between the planes of the benzene rings is 10.13 (9)°. Intra-molecular N-H⋯O hydrogen bond generate S(6) and S(5) loops. In the crystal, mol-ecules are connected by O-H⋯O hydrogen bonds, generating C(9) chains propagating in the [010] direction.

Related literature

For a related structure, see: Eltayeb et al. (2010 ▸). For background to Schiff bases and their applications, see: Blagus et al. (2010 ▸).

Experimental

Crystal data

C14H13NO2

M = 227.25

Orthorhombic,

a = 12.9474 (18) Å

b = 9.0660 (13) Å

c = 19.583 (3) Å

V = 2298.7 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▸) T min = 0.875, T max = 1.000

29481 measured reflections

2583 independent reflections

1810 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.130

S = 1.05

2583 reflections

163 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2009 ▸); cell refinement: SAINT (Bruker, 2009 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸) and PLATON (Spek, 2009 ▸); software used to prepare material for publication: SHELXL2014 and PLATON.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015006374/hb7370sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015006374/hb7370Isup2.hkl

Click here for additional data file.

ORTEP . DOI: 10.1107/S2056989015006374/hb7370fig1.tif

ORTEP Plot of (I) drawn at 40% probability level

Click here for additional data file.

. DOI: 10.1107/S2056989015006374/hb7370fig2.tif

A perspective view of the one-dimensional infinite chain in the title compound, (I), showing N—H⋯O and O—H⋯O hydrogen-bnd inter­actions as dashed lines. H atoms not involved in the inter­actions have been omitted for the sake of clarity.

CCDC reference: 1005919

Additional supporting information: crystallographic information; 3D view; checkCIF report

C14H13NO2	Dx = 1.313 Mg m−3
Mr = 227.25	Melting point: 355 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
a = 12.9474 (18) Å	Cell parameters from 500 reflections
b = 9.0660 (13) Å	θ = 5.0–50.0°
c = 19.583 (3) Å	µ = 0.09 mm−1
V = 2298.7 (6) Å3	T = 293 K
Z = 8	Block, colorless
F(000) = 960	0.3 × 0.25 × 0.20 mm

Bruker APEXII CCD diffractometer	1810 reflections with I > 2σ(I)
Radiation source: graphite monochromator	Rint = 0.059
OMEGA–PHI scans	θmax = 27.6°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −16→16
Tmin = 0.875, Tmax = 1.000	k = −11→8
29481 measured reflections	l = −25→25
2583 independent reflections

Refinement on F2	2 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.130	w = 1/[σ2(Fo2) + (0.0467P)2 + 1.0454P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.015
2583 reflections	Δρmax = 0.21 e Å−3
163 parameters	Δρmin = −0.20 e Å−3

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
H1	0.6541 (13)	0.138 (3)	0.2650 (11)	0.063 (7)*
H4	0.5002 (18)	0.378 (3)	0.1982 (14)	0.099 (9)*
N1	0.71804 (10)	0.16956 (16)	0.25537 (7)	0.0328 (3)
C8	0.78912 (12)	0.1022 (2)	0.29051 (8)	0.0345 (4)
H8	0.8579	0.1254	0.2819	0.041*
O1	0.58630 (9)	0.00525 (16)	0.31990 (7)	0.0465 (4)
C9	0.73191 (11)	0.2767 (2)	0.20440 (8)	0.0315 (4)
O2	0.55197 (9)	0.31121 (17)	0.20963 (7)	0.0494 (4)
C14	0.64308 (12)	0.3480 (2)	0.18036 (9)	0.0350 (4)
C5	0.66350 (13)	−0.0477 (2)	0.35492 (9)	0.0358 (4)
C10	0.82779 (13)	0.3143 (2)	0.17751 (9)	0.0389 (4)
H10	0.8872	0.2685	0.1937	0.047*
C4	0.76708 (12)	−0.0042 (2)	0.34097 (8)	0.0335 (4)
C2	0.83378 (15)	−0.1684 (2)	0.42880 (10)	0.0451 (5)
C13	0.65167 (14)	0.4516 (2)	0.12897 (9)	0.0415 (5)
H13	0.5928	0.4982	0.1124	0.050*
C6	0.64951 (14)	−0.1513 (2)	0.40786 (9)	0.0441 (5)
H6	0.5830	−0.1815	0.4191	0.053*
C11	0.83474 (14)	0.4189 (2)	0.12694 (10)	0.0462 (5)
H11	0.8990	0.4445	0.1094	0.055*
C3	0.84905 (13)	−0.0673 (2)	0.37804 (9)	0.0418 (5)
H3	0.9163	−0.0390	0.3676	0.050*
C7	0.73159 (15)	−0.2085 (2)	0.44311 (9)	0.0461 (5)
H7	0.7190	−0.2763	0.4778	0.055*
C12	0.74692 (16)	0.4864 (2)	0.10209 (9)	0.0457 (5)
H12	0.7520	0.5554	0.0671	0.055*
C1	0.92146 (18)	−0.2371 (3)	0.46830 (12)	0.0691 (7)
H1A	0.9742	−0.2687	0.4372	0.104*
H1B	0.8963	−0.3205	0.4935	0.104*
H1C	0.9497	−0.1658	0.4994	0.104*

	U11	U22	U33	U12	U13	U23
N1	0.0232 (6)	0.0327 (9)	0.0425 (8)	−0.0010 (6)	−0.0004 (6)	−0.0013 (6)
C8	0.0243 (7)	0.0355 (11)	0.0437 (9)	−0.0001 (7)	−0.0016 (7)	−0.0035 (8)
O1	0.0253 (6)	0.0571 (10)	0.0572 (8)	−0.0049 (6)	−0.0043 (5)	0.0051 (7)
C9	0.0267 (8)	0.0304 (10)	0.0372 (8)	−0.0001 (7)	−0.0005 (6)	−0.0027 (7)
O2	0.0249 (6)	0.0582 (10)	0.0651 (9)	0.0050 (6)	0.0004 (6)	0.0148 (7)
C14	0.0271 (8)	0.0381 (11)	0.0398 (9)	0.0005 (7)	−0.0008 (7)	−0.0029 (8)
C5	0.0305 (8)	0.0360 (11)	0.0410 (9)	−0.0041 (7)	0.0000 (7)	−0.0059 (8)
C10	0.0281 (8)	0.0410 (12)	0.0477 (10)	0.0032 (7)	0.0011 (7)	−0.0013 (8)
C4	0.0289 (8)	0.0332 (10)	0.0383 (8)	−0.0017 (7)	−0.0016 (7)	−0.0022 (7)
C2	0.0450 (10)	0.0474 (13)	0.0429 (10)	0.0017 (9)	−0.0054 (8)	0.0043 (9)
C13	0.0381 (9)	0.0443 (12)	0.0423 (10)	0.0050 (8)	−0.0062 (8)	0.0023 (8)
C6	0.0378 (9)	0.0485 (13)	0.0459 (10)	−0.0095 (8)	0.0057 (8)	0.0001 (9)
C11	0.0377 (10)	0.0494 (13)	0.0516 (11)	−0.0049 (9)	0.0109 (8)	0.0016 (9)
C3	0.0288 (8)	0.0483 (13)	0.0482 (10)	0.0004 (8)	−0.0034 (7)	0.0044 (9)
C7	0.0528 (11)	0.0463 (13)	0.0392 (9)	−0.0045 (9)	0.0019 (8)	0.0038 (9)
C12	0.0516 (11)	0.0447 (13)	0.0408 (9)	−0.0021 (9)	0.0033 (9)	0.0053 (9)
C1	0.0560 (13)	0.085 (2)	0.0662 (14)	0.0045 (12)	−0.0112 (11)	0.0278 (14)

N1—C8	1.301 (2)	C2—C3	1.367 (3)
N1—C9	1.404 (2)	C2—C7	1.400 (3)
N1—H1	0.895 (16)	C2—C1	1.508 (3)
C8—C4	1.410 (2)	C13—C12	1.377 (3)
C8—H8	0.9300	C13—H13	0.9300
O1—C5	1.304 (2)	C6—C7	1.369 (3)
C9—C10	1.391 (2)	C6—H6	0.9300
C9—C14	1.401 (2)	C11—C12	1.380 (3)
O2—C14	1.353 (2)	C11—H11	0.9300
O2—H4	0.932 (17)	C3—H3	0.9300
C14—C13	1.381 (3)	C7—H7	0.9300
C5—C6	1.410 (3)	C12—H12	0.9300
C5—C4	1.424 (2)	C1—H1A	0.9600
C10—C11	1.374 (3)	C1—H1B	0.9600
C10—H10	0.9300	C1—H1C	0.9600
C4—C3	1.407 (2)
C8—N1—C9	127.59 (14)	C12—C13—C14	120.40 (17)
C8—N1—H1	113.3 (15)	C12—C13—H13	119.8
C9—N1—H1	119.1 (15)	C14—C13—H13	119.8
N1—C8—C4	123.26 (15)	C7—C6—C5	121.52 (17)
N1—C8—H8	118.4	C7—C6—H6	119.2
C4—C8—H8	118.4	C5—C6—H6	119.2
C10—C9—C14	119.50 (16)	C10—C11—C12	120.41 (17)
C10—C9—N1	123.55 (15)	C10—C11—H11	119.8
C14—C9—N1	116.95 (14)	C12—C11—H11	119.8
C14—O2—H4	111.4 (18)	C2—C3—C4	122.59 (17)
O2—C14—C13	123.12 (15)	C2—C3—H3	118.7
O2—C14—C9	117.36 (16)	C4—C3—H3	118.7
C13—C14—C9	119.52 (15)	C6—C7—C2	122.30 (18)
O1—C5—C6	122.24 (16)	C6—C7—H7	118.9
O1—C5—C4	121.25 (16)	C2—C7—H7	118.9
C6—C5—C4	116.51 (16)	C13—C12—C11	120.12 (18)
C11—C10—C9	120.02 (16)	C13—C12—H12	119.9
C11—C10—H10	120.0	C11—C12—H12	119.9
C9—C10—H10	120.0	C2—C1—H1A	109.5
C3—C4—C8	119.13 (15)	C2—C1—H1B	109.5
C3—C4—C5	119.91 (16)	H1A—C1—H1B	109.5
C8—C4—C5	120.96 (15)	C2—C1—H1C	109.5
C3—C2—C7	117.15 (17)	H1A—C1—H1C	109.5
C3—C2—C1	122.77 (18)	H1B—C1—H1C	109.5
C7—C2—C1	120.08 (18)
C9—N1—C8—C4	179.90 (16)	O2—C14—C13—C12	178.77 (18)
C8—N1—C9—C10	8.4 (3)	C9—C14—C13—C12	−0.9 (3)
C8—N1—C9—C14	−171.45 (17)	O1—C5—C6—C7	178.47 (18)
C10—C9—C14—O2	−177.89 (16)	C4—C5—C6—C7	−1.0 (3)
N1—C9—C14—O2	2.0 (2)	C9—C10—C11—C12	−0.6 (3)
C10—C9—C14—C13	1.8 (3)	C7—C2—C3—C4	0.1 (3)
N1—C9—C14—C13	−178.31 (16)	C1—C2—C3—C4	179.5 (2)
C14—C9—C10—C11	−1.1 (3)	C8—C4—C3—C2	178.41 (19)
N1—C9—C10—C11	179.06 (17)	C5—C4—C3—C2	−1.3 (3)
N1—C8—C4—C3	−177.72 (17)	C5—C6—C7—C2	−0.2 (3)
N1—C8—C4—C5	2.0 (3)	C3—C2—C7—C6	0.7 (3)
O1—C5—C4—C3	−177.76 (17)	C1—C2—C7—C6	−178.8 (2)
C6—C5—C4—C3	1.7 (3)	C14—C13—C12—C11	−0.8 (3)
O1—C5—C4—C8	2.5 (3)	C10—C11—C12—C13	1.5 (3)
C6—C5—C4—C8	−177.99 (17)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H4···O1i	0.93 (2)	1.65 (2)	2.5756 (18)	176 (3)
N1—H1···O2	0.90 (2)	2.32 (2)	2.6598 (19)	102 (2)
N1—H1···O1	0.90 (2)	1.84 (2)	2.5933 (19)	141 (2)

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
O2H4O1i	0.93(2)	1.65(2)	2.5756(18)	176(3)
N1H1O2	0.90(2)	2.32(2)	2.6598(19)	102(2)
N1H1O1	0.90(2)	1.84(2)	2.5933(19)	141(2)

Symmetry code: (i) .