2-[2-(Hydro­xy­methyl)­phenyl­imino­methyl]­phenol

Molecules of the title compound, C₁₄H₁₃NO₂, are nearly planar. The molecular structure is stabilized by a strong intramolecular O—H...N hydrogen bond between the imine and hydroxyl groups [O...N = 2.614 (2) Å]. In the crystal structure, intermolecular O—H...O hydrogen bonds [O...O = 2.681 (3) and 2.641 (3) Å] link inversion-related mol­ecules into chains parallel to the a axis.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.044
• wR factor = 0.108
• Data-to-parameter ratio = 15.2

checkCIF/PLATON results

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Computing details

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, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

2-[(2-Hydroxymethylphenylimino)methyl]phenol

Crystal data

C14H13NO2	F(000) = 480
Mr = 227.25	Dx = 1.326 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5263 reflections
a = 4.5866 (4) Å	θ = 1.6–26.8°
b = 19.742 (2) Å	µ = 0.09 mm^−1
c = 12.6200 (11) Å	T = 293 K
β = 94.872 (7)°	Prism, yellow
V = 1138.60 (18) Å^3	0.33 × 0.22 × 0.13 mm
Z = 4

Data collection

Stoe IPDS-2 diffractometer	2471 independent reflections
Radiation source: fine-focus sealed tube	1329 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.046
Detector resolution: 6.67 pixels mm^-1	θmax = 27.1°, θmin = 1.9°
ω scans	h = −5→5
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −25→25
Tmin = 0.974, Tmax = 0.988	l = −16→16
11355 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 0.89	w = 1/[σ^2(Fo^2) + (0.06P)^2] where P = (Fo^2 + 2Fc^2)/3
2471 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.12 e Å^−3
2 restraints	Δρmin = −0.14 e Å^−3

Special details

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.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.2410 (4)	0.48673 (7)	0.45055 (13)	0.0689 (4)
H1A	0.099 (12)	0.484 (4)	0.486 (6)	0.17 (3)*	0.50
H1B	0.382 (8)	0.487 (3)	0.495 (4)	0.13 (3)*	0.50
O2	0.7430 (3)	0.27763 (7)	0.39930 (10)	0.0745 (4)
H2O	0.6201	0.3037	0.3713	0.112*
N1	0.3939 (3)	0.32954 (7)	0.24593 (10)	0.0480 (3)
C1	0.1851 (3)	0.37928 (7)	0.20926 (12)	0.0442 (4)
C2	0.0535 (4)	0.38271 (9)	0.10634 (14)	0.0582 (5)
H2	0.0983	0.3504	0.0566	0.070*
C3	−0.1433 (4)	0.43359 (9)	0.07721 (16)	0.0649 (5)
H3	−0.2305	0.4356	0.0080	0.078*
C4	−0.2100 (4)	0.48104 (9)	0.15004 (16)	0.0633 (5)
H4	−0.3434	0.5152	0.1304	0.076*
C5	−0.0813 (4)	0.47851 (9)	0.25193 (15)	0.0568 (5)
H5	−0.1278	0.5112	0.3007	0.068*
C6	0.1170 (3)	0.42804 (7)	0.28350 (12)	0.0456 (4)
C7	0.2588 (4)	0.42459 (9)	0.39480 (14)	0.0602 (5)
H7A	0.1652	0.3893	0.4333	0.072*
H7B	0.4630	0.4124	0.3925	0.072*
C8	0.4850 (4)	0.28428 (8)	0.18471 (14)	0.0510 (4)
H8	0.4070	0.2827	0.1143	0.061*
C9	0.7051 (4)	0.23537 (8)	0.22099 (13)	0.0487 (4)
C10	0.8272 (4)	0.23353 (8)	0.32558 (14)	0.0525 (4)
C11	1.0392 (4)	0.18592 (9)	0.35659 (16)	0.0651 (5)
H11	1.1207	0.1848	0.4266	0.078*
C12	1.1289 (4)	0.14034 (9)	0.28395 (18)	0.0689 (6)
H12	1.2710	0.1084	0.3053	0.083*
C13	1.0120 (5)	0.14117 (10)	0.18038 (19)	0.0731 (6)
H13	1.0746	0.1101	0.1317	0.088*
C14	0.8021 (4)	0.18817 (9)	0.14917 (16)	0.0672 (5)
H14	0.7226	0.1887	0.0789	0.081*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0663 (9)	0.0731 (9)	0.0664 (9)	0.0067 (8)	0.0002 (8)	−0.0276 (7)
O2	0.0852 (10)	0.0851 (9)	0.0514 (8)	0.0298 (8)	−0.0043 (7)	−0.0119 (7)
N1	0.0488 (8)	0.0484 (7)	0.0467 (8)	0.0014 (6)	0.0035 (6)	−0.0029 (6)
C1	0.0413 (8)	0.0460 (9)	0.0449 (9)	−0.0031 (7)	0.0011 (7)	0.0010 (7)
C2	0.0624 (11)	0.0622 (10)	0.0493 (10)	0.0030 (9)	0.0007 (9)	−0.0046 (8)
C3	0.0684 (12)	0.0691 (12)	0.0544 (11)	0.0042 (10)	−0.0111 (10)	0.0072 (9)
C4	0.0611 (11)	0.0561 (10)	0.0708 (13)	0.0083 (9)	−0.0051 (10)	0.0080 (9)
C5	0.0560 (10)	0.0512 (9)	0.0630 (12)	0.0057 (8)	0.0043 (9)	−0.0018 (8)
C6	0.0436 (9)	0.0473 (9)	0.0458 (9)	−0.0038 (7)	0.0038 (8)	−0.0010 (7)
C7	0.0724 (12)	0.0558 (10)	0.0513 (11)	0.0039 (9)	−0.0007 (9)	−0.0136 (8)
C8	0.0533 (10)	0.0537 (9)	0.0458 (10)	0.0008 (8)	0.0026 (8)	−0.0042 (7)
C9	0.0490 (9)	0.0448 (8)	0.0529 (11)	−0.0020 (7)	0.0066 (8)	−0.0034 (7)
C10	0.0540 (10)	0.0506 (9)	0.0538 (11)	0.0017 (8)	0.0106 (9)	0.0005 (8)
C11	0.0649 (12)	0.0655 (11)	0.0650 (12)	0.0117 (10)	0.0060 (10)	0.0112 (10)
C12	0.0637 (12)	0.0524 (10)	0.0927 (17)	0.0101 (9)	0.0194 (12)	0.0097 (10)
C13	0.0775 (13)	0.0565 (11)	0.0873 (17)	0.0129 (10)	0.0189 (12)	−0.0125 (10)
C14	0.0758 (13)	0.0630 (11)	0.0632 (12)	0.0064 (10)	0.0080 (10)	−0.0157 (9)

Geometric parameters (Å, º)

O1—C7	1.420 (2)	C5—H5	0.93
O1—H1A	0.82 (1)	C6—C7	1.498 (2)
O1—H1B	0.82 (1)	C7—H7A	0.97
O2—C10	1.354 (2)	C7—H7B	0.97
O2—H2O	0.82	C8—C9	1.443 (2)
N1—C8	1.275 (2)	C8—H8	0.93
N1—C1	1.421 (2)	C9—C10	1.390 (2)
C1—C2	1.387 (2)	C9—C14	1.399 (2)
C1—C6	1.397 (2)	C10—C11	1.384 (2)
C2—C3	1.380 (3)	C11—C12	1.372 (3)
C2—H2	0.93	C11—H11	0.93
C3—C4	1.365 (3)	C12—C13	1.370 (3)
C3—H3	0.93	C12—H12	0.93
C4—C5	1.370 (3)	C13—C14	1.371 (3)
C4—H4	0.93	C13—H13	0.93
C5—C6	1.385 (2)	C14—H14	0.93
C7—O1—H1A	108 (6)	C6—C7—H7A	109.0
C7—O1—H1B	106 (5)	O1—C7—H7B	109.0
H1A—O1—H1B	104 (7)	C6—C7—H7B	109.0
C10—O2—H2O	109.5	H7A—C7—H7B	107.8
C8—N1—C1	122.2 (2)	N1—C8—C9	122.2 (2)
C2—C1—C6	119.35 (15)	N1—C8—H8	118.9
C2—C1—N1	124.5 (2)	C9—C8—H8	118.9
C6—C1—N1	116.1 (2)	C10—C9—C14	118.24 (17)
C3—C2—C1	120.54 (17)	C10—C9—C8	122.24 (14)
C3—C2—H2	119.7	C14—C9—C8	119.51 (18)
C1—C2—H2	119.7	O2—C10—C11	118.5 (2)
C4—C3—C2	119.95 (19)	O2—C10—C9	121.3 (2)
C4—C3—H3	120.0	C11—C10—C9	120.19 (16)
C2—C3—H3	120.0	C12—C11—C10	120.0 (2)
C3—C4—C5	120.25 (18)	C12—C11—H11	120.0
C3—C4—H4	119.9	C10—C11—H11	120.0
C5—C4—H4	119.9	C13—C12—C11	120.94 (19)
C4—C5—C6	121.12 (17)	C13—C12—H12	119.5
C4—C5—H5	119.4	C11—C12—H12	119.5
C6—C5—H5	119.4	C12—C13—C14	119.38 (18)
C5—C6—C1	118.79 (16)	C12—C13—H13	120.3
C5—C6—C7	121.65 (15)	C14—C13—H13	120.3
C1—C6—C7	119.55 (14)	C13—C14—C9	121.3 (2)
O1—C7—C6	112.7 (2)	C13—C14—H14	119.4
O1—C7—H7A	109.0	C9—C14—H14	119.4
C8—N1—C1—C2	2.2 (2)	C1—N1—C8—C9	177.60 (14)
C8—N1—C1—C6	−176.58 (14)	N1—C8—C9—C10	1.4 (2)
C6—C1—C2—C3	−0.1 (2)	N1—C8—C9—C14	−178.17 (16)
N1—C1—C2—C3	−178.83 (15)	C14—C9—C10—O2	−179.85 (16)
C1—C2—C3—C4	−0.1 (3)	C8—C9—C10—O2	0.5 (2)
C2—C3—C4—C5	0.3 (3)	C14—C9—C10—C11	0.0 (2)
C3—C4—C5—C6	−0.3 (3)	C8—C9—C10—C11	−179.60 (16)
C4—C5—C6—C1	0.1 (2)	O2—C10—C11—C12	179.79 (17)
C4—C5—C6—C7	−179.83 (16)	C9—C10—C11—C12	−0.1 (3)
C2—C1—C6—C5	0.1 (2)	C10—C11—C12—C13	0.1 (3)
N1—C1—C6—C5	178.93 (13)	C11—C12—C13—C14	−0.1 (3)
C2—C1—C6—C7	−179.97 (15)	C12—C13—C14—C9	0.1 (3)
N1—C1—C6—C7	−1.1 (2)	C10—C9—C14—C13	0.0 (3)
C5—C6—C7—O1	−18.2 (2)	C8—C9—C14—C13	179.60 (17)
C1—C6—C7—O1	161.87 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O1^i	0.82 (1)	1.90 (3)	2.681 (3)	158 (7)
O1—H1B···O1^ii	0.82 (1)	1.87 (3)	2.641 (3)	155 (6)
O2—H2O···N1	0.82	1.89	2.614 (2)	147
C5—H5···O1	0.93	2.48	2.804 (3)	101

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z+1.