2-[(4-Chloro-phen-yl)imino-meth-yl]hydro-quinone.

The title compound, C(13)H(10)ClNO(2), exists in the phenol-imine form in the crystal, and the aromatic rings are oriented at a dihedral angle of 2.82 (9)°. An intra-molecular O-H⋯N hydrogen bond results in the formation of a planar six-membered ring. In the crystal structure, inter-molecular O-H⋯O hydrogen bonds link the mol-ecules into chains.

Related literature

For general background to o-hydr­oxy Schiff bases, see: Calligaris et al. (1972 ▶); Hadjoudis et al. (1987 ▶); Hökelek et al. (2004 ▶); Maslen & Waters (1975 ▶); Moustakali-Mavridis et al. (1980 ▶); Xu et al. (1994 ▶). For related structures, see: Filarowski et al. (2003 ▶); Karadayı et al. (2003 ▶); Yıldız et al. (1998 ▶).

Experimental

Crystal data

C13H10ClNO2

M = 247.67

Monoclinic,

a = 20.3347 (14) Å

b = 4.5848 (2) Å

c = 12.0383 (9) Å

β = 98.231 (6)°

V = 1110.78 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.33 mm−1

T = 296 K

0.80 × 0.40 × 0.06 mm

Data collection

Stoe IPDS-II diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.819, T max = 0.978

15373 measured reflections

2185 independent reflections

1575 reflections with I > 2σ(I)

R int = 0.069

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.091

S = 0.95

2185 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.25 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-RED32 (Stoe & Cie, 2002 ▶); data reduction: X-RED32; 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/S1600536809015396/hk2670sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809015396/hk2670Isup2.hkl

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

C13H10ClNO2	F(000) = 512
Mr = 247.67	Dx = 1.481 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 13223 reflections
a = 20.3347 (14) Å	θ = 1.7–27.2°
b = 4.5848 (2) Å	µ = 0.33 mm−1
c = 12.0383 (9) Å	T = 296 K
β = 98.231 (6)°	Plate, brown
V = 1110.78 (12) Å3	0.80 × 0.40 × 0.06 mm
Z = 4

Stoe IPDS-II diffractometer	2185 independent reflections
Radiation source: fine-focus sealed tube	1575 reflections with I > 2σ(I)
graphite	Rint = 0.069
Detector resolution: 6.67 pixels mm-1	θmax = 26.0°, θmin = 2.0°
ω scans	h = −25→25
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −5→5
Tmin = 0.819, Tmax = 0.978	l = −14→14
15373 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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091	H-atom parameters constrained
S = 0.95	w = 1/[σ2(Fo2) + (0.0571P)2] where P = (Fo2 + 2Fc2)/3
2185 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.13 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

Experimental. 370 frames, detector distance = 120 mm

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.

	x	y	z	Uiso*/Ueq
Cl1	0.46483 (2)	1.40871 (10)	0.33464 (4)	0.06076 (18)
O1	0.21937 (7)	0.2322 (3)	0.60021 (10)	0.0600 (4)
H1	0.2441	0.3500	0.5759	0.090*
O2	0.03814 (6)	−0.1943 (3)	0.25297 (11)	0.0554 (3)
H2	0.0127	−0.3115	0.2757	0.083*
N1	0.26643 (6)	0.5541 (3)	0.44912 (11)	0.0404 (3)
C1	0.31206 (7)	0.7617 (3)	0.41651 (14)	0.0390 (3)
C2	0.35972 (8)	0.8701 (4)	0.50029 (14)	0.0469 (4)
H2A	0.3599	0.8079	0.5739	0.056*
C3	0.40681 (8)	1.0686 (4)	0.47659 (15)	0.0491 (4)
H3	0.4388	1.1380	0.5334	0.059*
C4	0.40585 (8)	1.1623 (3)	0.36807 (15)	0.0445 (4)
C5	0.35838 (9)	1.0629 (4)	0.28379 (15)	0.0499 (4)
H5	0.3578	1.1304	0.2108	0.060*
C6	0.31162 (8)	0.8628 (4)	0.30758 (14)	0.0480 (4)
H6	0.2796	0.7954	0.2504	0.058*
C7	0.22399 (8)	0.4302 (3)	0.37519 (13)	0.0409 (4)
H7	0.2238	0.4777	0.3000	0.049*
C8	0.17625 (7)	0.2186 (3)	0.40433 (13)	0.0384 (3)
C9	0.13019 (8)	0.1001 (3)	0.31857 (14)	0.0421 (4)
H9	0.1312	0.1561	0.2446	0.051*
C10	0.08364 (8)	−0.0975 (3)	0.34244 (14)	0.0427 (4)
C11	0.08231 (9)	−0.1840 (4)	0.45228 (16)	0.0510 (4)
H11	0.0504	−0.3164	0.4686	0.061*
C12	0.12807 (9)	−0.0745 (4)	0.53729 (15)	0.0530 (4)
H12	0.1274	−0.1360	0.6107	0.064*
C13	0.17529 (8)	0.1273 (4)	0.51433 (13)	0.0436 (4)

	U11	U22	U33	U12	U13	U23
Cl1	0.0545 (3)	0.0499 (3)	0.0821 (4)	−0.0131 (2)	0.0244 (2)	−0.0049 (2)
O1	0.0675 (8)	0.0733 (8)	0.0374 (7)	−0.0226 (7)	0.0010 (6)	0.0007 (6)
O2	0.0450 (7)	0.0519 (7)	0.0651 (8)	−0.0090 (5)	−0.0062 (6)	−0.0033 (6)
N1	0.0395 (7)	0.0397 (7)	0.0417 (7)	−0.0030 (6)	0.0047 (6)	−0.0009 (6)
C1	0.0380 (8)	0.0355 (7)	0.0436 (9)	−0.0002 (6)	0.0065 (7)	−0.0012 (7)
C2	0.0499 (9)	0.0477 (9)	0.0426 (9)	−0.0046 (7)	0.0049 (7)	−0.0003 (7)
C3	0.0448 (9)	0.0481 (9)	0.0527 (11)	−0.0080 (8)	0.0012 (7)	−0.0062 (8)
C4	0.0402 (9)	0.0367 (8)	0.0590 (11)	−0.0017 (6)	0.0148 (8)	−0.0036 (7)
C5	0.0546 (10)	0.0507 (9)	0.0457 (10)	−0.0048 (8)	0.0115 (8)	0.0037 (8)
C6	0.0469 (9)	0.0514 (10)	0.0446 (10)	−0.0094 (7)	0.0025 (7)	0.0003 (8)
C7	0.0436 (8)	0.0408 (8)	0.0383 (9)	−0.0014 (7)	0.0062 (7)	0.0019 (7)
C8	0.0380 (8)	0.0371 (8)	0.0400 (9)	0.0013 (6)	0.0050 (7)	−0.0007 (6)
C9	0.0445 (9)	0.0414 (8)	0.0398 (9)	0.0004 (7)	0.0036 (7)	0.0026 (7)
C10	0.0360 (8)	0.0390 (8)	0.0514 (10)	0.0006 (7)	0.0008 (7)	−0.0037 (7)
C11	0.0454 (10)	0.0472 (9)	0.0622 (12)	−0.0074 (7)	0.0141 (8)	0.0023 (8)
C12	0.0591 (11)	0.0559 (10)	0.0458 (10)	−0.0076 (9)	0.0138 (8)	0.0056 (8)
C13	0.0444 (9)	0.0474 (9)	0.0391 (9)	−0.0027 (7)	0.0060 (7)	−0.0019 (7)

O1—H1	0.8200	C7—N1	1.280 (2)
O2—H2	0.8200	C7—C8	1.451 (2)
C1—C2	1.387 (2)	C7—H7	0.9300
C1—C6	1.390 (2)	C8—C13	1.392 (2)
C1—N1	1.4229 (19)	C8—C9	1.401 (2)
C2—C3	1.380 (2)	C9—C10	1.370 (2)
C2—H2A	0.9300	C9—H9	0.9300
C3—C4	1.373 (3)	C10—C11	1.384 (2)
C3—H3	0.9300	C10—O2	1.3883 (19)
C4—C5	1.374 (2)	C11—C12	1.376 (3)
C4—Cl1	1.7365 (16)	C11—H11	0.9300
C5—C6	1.381 (2)	C12—C13	1.389 (2)
C5—H5	0.9300	C12—H12	0.9300
C6—H6	0.9300	C13—O1	1.3557 (19)
C13—O1—H1	109.5	N1—C7—C8	122.44 (14)
C10—O2—H2	109.5	N1—C7—H7	118.8
C7—N1—C1	120.41 (14)	C8—C7—H7	118.8
C2—C1—C6	118.42 (15)	C13—C8—C9	119.06 (15)
C2—C1—N1	117.03 (14)	C13—C8—C7	122.16 (14)
C6—C1—N1	124.55 (14)	C9—C8—C7	118.78 (14)
C3—C2—C1	121.29 (16)	C10—C9—C8	120.75 (15)
C3—C2—H2A	119.4	C10—C9—H9	119.6
C1—C2—H2A	119.4	C8—C9—H9	119.6
C4—C3—C2	119.16 (16)	C9—C10—C11	119.88 (15)
C4—C3—H3	120.4	C9—C10—O2	116.90 (15)
C2—C3—H3	120.4	C11—C10—O2	123.20 (15)
C3—C4—C5	120.78 (15)	C12—C11—C10	120.16 (16)
C3—C4—Cl1	120.53 (13)	C12—C11—H11	119.9
C5—C4—Cl1	118.69 (14)	C10—C11—H11	119.9
C4—C5—C6	119.93 (16)	C11—C12—C13	120.54 (16)
C4—C5—H5	120.0	C11—C12—H12	119.7
C6—C5—H5	120.0	C13—C12—H12	119.7
C5—C6—C1	120.39 (15)	O1—C13—C12	118.99 (15)
C5—C6—H6	119.8	O1—C13—C8	121.41 (14)
C1—C6—H6	119.8	C12—C13—C8	119.59 (15)
C8—C7—N1—C1	−179.65 (13)	N1—C7—C8—C9	178.06 (15)
C2—C1—N1—C7	−175.30 (14)	C13—C8—C9—C10	1.7 (2)
C6—C1—N1—C7	5.2 (2)	C7—C8—C9—C10	−179.12 (14)
C6—C1—C2—C3	−1.5 (2)	C8—C9—C10—C11	−0.7 (2)
N1—C1—C2—C3	178.92 (14)	C8—C9—C10—O2	177.31 (14)
C1—C2—C3—C4	0.7 (3)	C9—C10—C11—C12	−0.7 (3)
C2—C3—C4—C5	0.6 (3)	O2—C10—C11—C12	−178.57 (15)
C2—C3—C4—Cl1	−179.27 (12)	C10—C11—C12—C13	1.1 (3)
C3—C4—C5—C6	−1.1 (3)	C11—C12—C13—O1	179.57 (16)
Cl1—C4—C5—C6	178.81 (13)	C11—C12—C13—C8	−0.1 (3)
C4—C5—C6—C1	0.2 (3)	C9—C8—C13—O1	179.08 (14)
C2—C1—C6—C5	1.1 (2)	C7—C8—C13—O1	−0.1 (2)
N1—C1—C6—C5	−179.43 (15)	C9—C8—C13—C12	−1.3 (2)
N1—C7—C8—C13	−2.7 (2)	C7—C8—C13—C12	179.54 (15)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.90	2.6270 (18)	147
O2—H2···O2i	0.82	2.04	2.7631 (13)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.90	2.6270 (18)	147
O2—H2⋯O2i	0.82	2.04	2.7631 (13)	147

Symmetry code: (i) .