2-(Anilinometh­yl)phenol

In the title compound, C₁₃H₁₃NO, which was synthesized by the reduction of 2-(phenyl­imino­meth­yl)phenol, the dihedral angle between the two benzene ring planes is 71.08 (4)°. The crystal structure exhibits the formation of centrosymmetric dimers by inter­molecular O—H...N hydrogen bonds, characterized by an R₂²(12) pattern. These dimers are further connected by N—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C)= 0.002 Å
• R factor = 0.041
• wR factor = 0.108
• Data-to-parameter ratio = 13.8

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S1. Comment

The structure of 2-(phenyliminomethyl)phenol is known (Arod et al., 2005). We report herein the crystal structure of its reductive product which is a bidentate ligand (Baker et al., 1992) (Fig. 1).

The bond lengths and angles are within normal ranges (Aguiari et al., 1992; Jeevanandam et al., 2000). The dihedral angle between the two phenyl ring planes is 71.08 (4)°. Centro-symmetric dimers are formed by intermolecular O—H···N hydrogen bonds characterized by an R₂²(12) pattern, which are further connected by N—H···O hydrogen bonds (Table 1).

Related literature

For related literature, see: Aguiari et al. (1992); Arod et al. (2005); Baker et al. (1992); Jeevanandam et al.(2000); Noda (1959).

S2. Experimental

The title compound was synthesized by the reaction of 2-(phenyliminomethyl)phenol (1.97 g, 10 mmol) with NaBH₄ (0.38 g, 10 mmol) in 60 ml me thanol according to the reported method (Noda, 1959). Crystals were obtained from an ethanolic (95%) solution by slow evaporation at room temperature.

S3. Refinement

H atoms bonded to O and C were placed at calculated positions and were included in the refinement in the riding-model approximation, with C—H = 0.93 Å and for aromatic H atoms, C—H = 0.97 Å for methylene H atoms, O—H = 0.82 Å and U_iso(H) = 1.2Ueq(C). The H atom on N atom was freely refined.

Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures

Fig. 1. The structure of (I), with displacement ellipsoids are drawn at the 30% probability level.

2-(Anilinomethyl)phenol

Crystal data

C13H13NO	Z = 2
Mr = 199.24	F(000) = 212
Triclinic, P1	Dx = 1.265 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.5911 (16) Å	Cell parameters from 1673 reflections
b = 7.932 (2) Å	θ = 2.6–27.2°
c = 11.803 (3) Å	µ = 0.08 mm^−1
α = 90.649 (5)°	T = 295 K
β = 91.985 (4)°	Prism, colorless
γ = 90.323 (5)°	0.45 × 0.08 × 0.06 mm
V = 523.1 (2) Å^3

Data collection

Bruker SMART APEX detector diffractometer	1943 independent reflections
Radiation source: fine-focus sealed tube	1632 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
ϕ and ω scans	θmax = 25.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −6→6
Tmin = 0.965, Tmax = 0.989	k = −9→9
3981 measured reflections	l = −14→14

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0537P)^2 + 0.0635P] where P = (Fo^2 + 2Fc^2)/3
1943 reflections	(Δ/σ)max < 0.001
141 parameters	Δρmax = 0.14 e Å^−3
0 restraints	Δρmin = −0.19 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
H1A	0.524 (3)	0.7013 (18)	0.9462 (12)	0.043 (4)*
N1	0.6501 (2)	0.70555 (13)	0.90607 (9)	0.0385 (3)
O1	1.20706 (16)	0.62179 (11)	1.04289 (7)	0.0440 (3)
H1	1.2523	0.5298	1.0659	0.066*
C1	0.8734 (2)	0.79374 (16)	1.08012 (11)	0.0391 (3)
C2	1.0614 (2)	0.69432 (15)	1.12069 (10)	0.0360 (3)
C3	1.1025 (2)	0.67500 (18)	1.23582 (11)	0.0452 (3)
H3	1.2296	0.6095	1.2623	0.054*
C4	0.9552 (3)	0.7527 (2)	1.31168 (12)	0.0532 (4)
H4	0.9828	0.7387	1.3891	0.064*
C5	0.7681 (3)	0.8508 (2)	1.27337 (13)	0.0568 (4)
H5	0.6687	0.9030	1.3245	0.068*
C6	0.7296 (3)	0.87091 (19)	1.15865 (13)	0.0511 (4)
H6	0.6036	0.9381	1.1330	0.061*
C7	0.8315 (2)	0.82149 (17)	0.95536 (11)	0.0431 (3)
H7A	0.7802	0.9367	0.9433	0.052*
H7B	0.9806	0.8057	0.9170	0.052*
C8	0.5870 (2)	0.72473 (15)	0.78965 (11)	0.0382 (3)
C9	0.7269 (3)	0.81622 (19)	0.71694 (12)	0.0484 (4)
H9	0.8623	0.8735	0.7451	0.058*
C10	0.6651 (3)	0.8221 (2)	0.60285 (13)	0.0601 (4)
H10	0.7602	0.8832	0.5547	0.072*
C11	0.4659 (3)	0.7395 (2)	0.55931 (13)	0.0643 (5)
H11	0.4264	0.7436	0.4822	0.077*
C12	0.3253 (3)	0.6506 (2)	0.63132 (14)	0.0633 (5)
H12	0.1889	0.5952	0.6026	0.076*
C13	0.3841 (3)	0.64261 (19)	0.74551 (12)	0.0506 (4)
H13	0.2874	0.5819	0.7932	0.061*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0351 (6)	0.0424 (6)	0.0382 (6)	0.0004 (5)	0.0039 (5)	0.0043 (5)
O1	0.0447 (6)	0.0436 (5)	0.0445 (5)	0.0068 (4)	0.0089 (4)	0.0043 (4)
C1	0.0363 (7)	0.0364 (7)	0.0443 (7)	−0.0025 (5)	−0.0008 (5)	0.0009 (5)
C2	0.0342 (7)	0.0333 (6)	0.0407 (7)	−0.0037 (5)	0.0034 (5)	−0.0006 (5)
C3	0.0437 (8)	0.0477 (8)	0.0439 (8)	0.0024 (6)	−0.0041 (6)	0.0022 (6)
C4	0.0596 (10)	0.0618 (9)	0.0381 (7)	−0.0005 (7)	0.0012 (7)	−0.0063 (7)
C5	0.0555 (9)	0.0622 (10)	0.0533 (9)	0.0066 (8)	0.0117 (7)	−0.0125 (7)
C6	0.0433 (8)	0.0513 (8)	0.0587 (9)	0.0104 (6)	0.0009 (7)	−0.0016 (7)
C7	0.0405 (7)	0.0415 (7)	0.0471 (8)	−0.0010 (6)	−0.0021 (6)	0.0077 (6)
C8	0.0388 (7)	0.0374 (7)	0.0385 (7)	0.0086 (5)	0.0032 (5)	0.0019 (5)
C9	0.0445 (8)	0.0562 (9)	0.0446 (8)	−0.0005 (6)	0.0033 (6)	0.0058 (6)
C10	0.0632 (10)	0.0731 (11)	0.0450 (9)	0.0025 (8)	0.0103 (7)	0.0109 (7)
C11	0.0764 (12)	0.0783 (11)	0.0378 (8)	0.0056 (9)	−0.0038 (8)	0.0015 (7)
C12	0.0626 (10)	0.0726 (11)	0.0537 (9)	−0.0068 (8)	−0.0116 (8)	−0.0040 (8)
C13	0.0490 (9)	0.0543 (9)	0.0483 (8)	−0.0050 (7)	0.0000 (6)	0.0024 (6)

Geometric parameters (Å, º)

N1—C8	1.4168 (17)	C6—H6	0.9300
N1—C7	1.4663 (17)	C7—H7A	0.9700
N1—H1A	0.861 (16)	C7—H7B	0.9700
O1—C2	1.3722 (15)	C8—C13	1.3878 (19)
O1—H1	0.8200	C8—C9	1.3890 (19)
C1—C6	1.3874 (19)	C9—C10	1.380 (2)
C1—C2	1.3923 (19)	C9—H9	0.9300
C1—C7	1.5019 (18)	C10—C11	1.370 (2)
C2—C3	1.3806 (19)	C10—H10	0.9300
C3—C4	1.380 (2)	C11—C12	1.376 (2)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.374 (2)	C12—C13	1.379 (2)
C4—H4	0.9300	C12—H12	0.9300
C5—C6	1.375 (2)	C13—H13	0.9300
C5—H5	0.9300
C8—N1—C7	117.13 (11)	N1—C7—H7A	109.2
C8—N1—H1A	111.0 (9)	C1—C7—H7A	109.2
C7—N1—H1A	111.9 (10)	N1—C7—H7B	109.2
C2—O1—H1	109.5	C1—C7—H7B	109.2
C6—C1—C2	117.99 (12)	H7A—C7—H7B	107.9
C6—C1—C7	120.76 (12)	C13—C8—C9	118.75 (13)
C2—C1—C7	121.23 (12)	C13—C8—N1	118.78 (12)
O1—C2—C3	121.68 (12)	C9—C8—N1	122.39 (12)
O1—C2—C1	117.82 (11)	C10—C9—C8	120.00 (14)
C3—C2—C1	120.47 (12)	C10—C9—H9	120.0
C4—C3—C2	120.10 (13)	C8—C9—H9	120.0
C4—C3—H3	119.9	C11—C10—C9	121.12 (15)
C2—C3—H3	119.9	C11—C10—H10	119.4
C5—C4—C3	120.34 (14)	C9—C10—H10	119.4
C5—C4—H4	119.8	C10—C11—C12	119.03 (15)
C3—C4—H4	119.8	C10—C11—H11	120.5
C4—C5—C6	119.28 (14)	C12—C11—H11	120.5
C4—C5—H5	120.4	C11—C12—C13	120.81 (15)
C6—C5—H5	120.4	C11—C12—H12	119.6
C5—C6—C1	121.82 (14)	C13—C12—H12	119.6
C5—C6—H6	119.1	C12—C13—C8	120.29 (14)
C1—C6—H6	119.1	C12—C13—H13	119.9
N1—C7—C1	111.91 (11)	C8—C13—H13	119.9
C6—C1—C2—O1	−178.32 (11)	C6—C1—C7—N1	−85.36 (15)
C7—C1—C2—O1	−0.22 (18)	C2—C1—C7—N1	96.59 (15)
C6—C1—C2—C3	−0.41 (19)	C7—N1—C8—C13	−166.89 (12)
C7—C1—C2—C3	177.69 (12)	C7—N1—C8—C9	16.20 (18)
O1—C2—C3—C4	178.62 (12)	C13—C8—C9—C10	−1.0 (2)
C1—C2—C3—C4	0.8 (2)	N1—C8—C9—C10	175.95 (13)
C2—C3—C4—C5	−0.5 (2)	C8—C9—C10—C11	0.3 (2)
C3—C4—C5—C6	−0.1 (2)	C9—C10—C11—C12	0.5 (3)
C4—C5—C6—C1	0.5 (2)	C10—C11—C12—C13	−0.7 (3)
C2—C1—C6—C5	−0.2 (2)	C11—C12—C13—C8	0.0 (3)
C7—C1—C6—C5	−178.35 (13)	C9—C8—C13—C12	0.8 (2)
C8—N1—C7—C1	177.20 (11)	N1—C8—C13—C12	−176.24 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1^i	0.82	1.98	2.7871 (16)	170
N1—H1A···O1^ii	0.864 (16)	2.233 (16)	3.0770 (17)	165.8 (13)

Symmetry codes: (i) −x+2, −y+1, −z+2; (ii) x−1, y, z.