3-[(2,4-Dichloro-phen-yl)imino-meth-yl]-2-hydr-oxy-5-methyl-benzaldehyde.

The title compound, C(15)H(11)Cl(2)NO(2), is a Schiff base which adopts the phenol-imine tautomeric form in the solid state, being stabilized by a strong intra-molecular O-H⋯N hydrogen bond. The mol-ecule is almost planar (r.m.s. deviation for all non-H atoms = 0.049 Å), displaying a dihedral angle of 3.1 (3)° between the planes of the two aromatic rings.

Related literature

For Schiff bases as substrates in the preparation of number of biologically active compounds, see: Siddiqui et al. (2006 ▶). For photochromism and thermochromism in these compounds, see: Hadjoudis et al. (1987 ▶); Xu et al. (1994 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related structures, see: Gül et al. (2007 ▶) Koşar et al. (2005 ▶).

Experimental

Crystal data

C15H11Cl2NO2

M = 308.15

Monoclinic,

a = 19.424 (2) Å

b = 4.6113 (3) Å

c = 15.4245 (14) Å

β = 103.946 (8)°

V = 1340.9 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.48 mm−1

T = 296 K

0.80 × 0.31 × 0.02 mm

Data collection

Stoe IPDS II diffractometer

Absorption correction: integration (X-RED; Stoe & Cie, 2002 ▶) T min = 0.817, T max = 0.982

5912 measured reflections

2613 independent reflections

1228 reflections with I > 2σ(I)

R int = 0.099

Refinement

R[F 2 > 2σ(F 2)] = 0.063

wR(F 2) = 0.138

S = 0.91

2613 reflections

183 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.27 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/S1600536809018303/bt2960sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018303/bt2960Isup2.hkl

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

C15H11Cl2NO2	F(000) = 632
Mr = 308.15	Dx = 1.526 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6202 reflections
a = 19.424 (2) Å	θ = 1.9–29.5°
b = 4.6113 (3) Å	µ = 0.48 mm−1
c = 15.4245 (14) Å	T = 296 K
β = 103.946 (8)°	Plate, red
V = 1340.9 (2) Å3	0.80 × 0.31 × 0.02 mm
Z = 4

Stoe IPDS II diffractometer	2613 independent reflections
Radiation source: fine-focus sealed tube	1228 reflections with I > 2σ(I)
plane graphite	Rint = 0.099
Detector resolution: 6.67 pixels mm-1	θmax = 26.0°, θmin = 2.2°
rotation method scans	h = −23→22
Absorption correction: integration (X-RED; Stoe & Cie, 2002)	k = −5→5
Tmin = 0.817, Tmax = 0.982	l = −18→18
5912 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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138	H-atom parameters constrained
S = 0.91	w = 1/[σ2(Fo2) + (0.0441P)2] where P = (Fo2 + 2Fc2)/3
2613 reflections	(Δ/σ)max < 0.001
183 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

Experimental. 120 frames, detector distance = 100 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
C1	0.1925 (3)	0.2637 (10)	0.3175 (3)	0.0447 (12)
C2	0.1516 (3)	0.0564 (11)	0.2629 (3)	0.0489 (12)
C3	0.0969 (3)	−0.0806 (10)	0.2900 (3)	0.0495 (13)
H3	0.0702	−0.2192	0.2528	0.059*
C4	0.0806 (2)	−0.0190 (10)	0.3702 (3)	0.0467 (12)
C5	0.1227 (2)	0.1889 (10)	0.4239 (3)	0.0472 (12)
H5	0.1134	0.2321	0.4789	0.057*
C6	0.1770 (2)	0.3330 (9)	0.3998 (3)	0.0410 (11)
C7	0.2183 (3)	0.5467 (10)	0.4580 (3)	0.0463 (12)
H7	0.2062	0.5931	0.5110	0.056*
C8	0.3140 (2)	0.8812 (9)	0.4948 (3)	0.0435 (11)
C9	0.3702 (3)	1.0022 (10)	0.4659 (3)	0.0493 (13)
C10	0.4154 (3)	1.2028 (10)	0.5178 (3)	0.0538 (14)
H10	0.4531	1.2807	0.4980	0.065*
C11	0.4039 (3)	1.2842 (10)	0.5983 (3)	0.0496 (13)
C12	0.3487 (3)	1.1723 (10)	0.6292 (3)	0.0508 (13)
H12	0.3419	1.2297	0.6843	0.061*
C13	0.3035 (3)	0.9738 (10)	0.5774 (3)	0.0500 (13)
H13	0.2656	0.9003	0.5976	0.060*
C14	0.0213 (3)	−0.1709 (12)	0.3997 (3)	0.0618 (15)
H14A	−0.0188	−0.0434	0.3918	0.093*
H14B	0.0370	−0.2233	0.4615	0.093*
H14C	0.0079	−0.3426	0.3644	0.093*
C15	0.1671 (3)	−0.0215 (13)	0.1781 (3)	0.0676 (16)
H15	0.2055	0.0712	0.1638	0.081*
Cl1	0.38664 (8)	0.8931 (3)	0.36584 (9)	0.0671 (5)
Cl2	0.46096 (7)	1.5343 (3)	0.66358 (9)	0.0634 (5)
N1	0.2710 (2)	0.6740 (8)	0.4391 (2)	0.0464 (10)
O1	0.24635 (18)	0.3927 (7)	0.2904 (2)	0.0581 (10)
H1	0.2660	0.5101	0.3282	0.087*
O2	0.1350 (2)	−0.1956 (9)	0.1242 (2)	0.0785 (12)

	U11	U22	U33	U12	U13	U23
C1	0.046 (3)	0.044 (3)	0.045 (3)	0.000 (2)	0.012 (2)	0.003 (2)
C2	0.051 (3)	0.056 (3)	0.039 (2)	0.002 (3)	0.010 (2)	−0.004 (2)
C3	0.055 (3)	0.050 (3)	0.041 (3)	−0.002 (2)	0.006 (2)	−0.005 (2)
C4	0.043 (3)	0.047 (3)	0.048 (3)	0.003 (2)	0.009 (2)	0.000 (2)
C5	0.050 (3)	0.049 (3)	0.042 (2)	0.005 (2)	0.010 (2)	−0.001 (2)
C6	0.047 (3)	0.037 (3)	0.037 (2)	0.001 (2)	0.006 (2)	−0.003 (2)
C7	0.055 (3)	0.044 (3)	0.041 (2)	0.005 (3)	0.015 (2)	0.004 (2)
C8	0.045 (3)	0.037 (3)	0.046 (3)	−0.001 (2)	0.005 (2)	0.002 (2)
C9	0.057 (3)	0.041 (3)	0.046 (3)	0.005 (3)	0.004 (2)	0.000 (2)
C10	0.052 (3)	0.045 (3)	0.061 (3)	−0.005 (2)	0.008 (3)	0.000 (2)
C11	0.052 (3)	0.043 (3)	0.049 (3)	0.003 (2)	0.002 (2)	0.001 (2)
C12	0.058 (3)	0.052 (3)	0.045 (3)	0.005 (3)	0.017 (2)	−0.001 (2)
C13	0.053 (3)	0.055 (3)	0.044 (3)	−0.006 (3)	0.017 (2)	−0.003 (2)
C14	0.063 (3)	0.062 (4)	0.062 (3)	−0.003 (3)	0.018 (3)	−0.007 (3)
C15	0.063 (3)	0.089 (4)	0.054 (3)	−0.012 (3)	0.021 (3)	−0.018 (3)
Cl1	0.0730 (9)	0.0789 (10)	0.0548 (7)	−0.0040 (8)	0.0263 (7)	−0.0082 (7)
Cl2	0.0617 (8)	0.0510 (8)	0.0691 (8)	−0.0052 (7)	−0.0007 (7)	−0.0080 (7)
N1	0.053 (2)	0.046 (2)	0.039 (2)	0.003 (2)	0.0093 (19)	−0.0035 (18)
O1	0.061 (2)	0.063 (2)	0.0516 (19)	−0.0117 (18)	0.0160 (17)	−0.0102 (17)
O2	0.086 (3)	0.101 (3)	0.052 (2)	−0.028 (2)	0.023 (2)	−0.026 (2)

C1—O1	1.354 (6)	C8—N1	1.416 (5)
C1—C2	1.390 (6)	C9—C10	1.390 (6)
C1—C6	1.411 (7)	C9—Cl1	1.725 (5)
C2—C3	1.384 (7)	C10—C11	1.366 (7)
C2—C15	1.457 (7)	C10—H10	0.9300
C3—C4	1.378 (7)	C11—C12	1.374 (7)
C3—H3	0.9300	C11—Cl2	1.742 (5)
C4—C5	1.395 (6)	C12—C13	1.382 (6)
C4—C14	1.510 (7)	C12—H12	0.9300
C5—C6	1.371 (6)	C13—H13	0.9300
C5—H5	0.9300	C14—H14A	0.9600
C6—C7	1.440 (6)	C14—H14B	0.9600
C7—N1	1.272 (6)	C14—H14C	0.9600
C7—H7	0.9300	C15—O2	1.215 (5)
C8—C9	1.391 (7)	C15—H15	0.9300
C8—C13	1.404 (7)	O1—H1	0.8200
O1—C1—C2	119.2 (4)	C10—C9—Cl1	118.8 (4)
O1—C1—C6	121.8 (4)	C8—C9—Cl1	119.9 (4)
C2—C1—C6	119.1 (5)	C11—C10—C9	119.2 (5)
C3—C2—C1	120.0 (4)	C11—C10—H10	120.4
C3—C2—C15	120.0 (4)	C9—C10—H10	120.4
C1—C2—C15	120.0 (5)	C10—C11—C12	121.6 (5)
C4—C3—C2	122.4 (4)	C10—C11—Cl2	119.1 (4)
C4—C3—H3	118.8	C12—C11—Cl2	119.3 (4)
C2—C3—H3	118.8	C11—C12—C13	119.3 (5)
C3—C4—C5	116.5 (5)	C11—C12—H12	120.4
C3—C4—C14	122.1 (4)	C13—C12—H12	120.4
C5—C4—C14	121.4 (5)	C12—C13—C8	120.9 (5)
C6—C5—C4	123.4 (5)	C12—C13—H13	119.5
C6—C5—H5	118.3	C8—C13—H13	119.5
C4—C5—H5	118.3	C4—C14—H14A	109.5
C5—C6—C1	118.6 (4)	C4—C14—H14B	109.5
C5—C6—C7	120.8 (4)	H14A—C14—H14B	109.5
C1—C6—C7	120.5 (5)	C4—C14—H14C	109.5
N1—C7—C6	122.1 (5)	H14A—C14—H14C	109.5
N1—C7—H7	118.9	H14B—C14—H14C	109.5
C6—C7—H7	118.9	O2—C15—C2	126.4 (5)
C9—C8—C13	117.8 (4)	O2—C15—H15	116.8
C9—C8—N1	118.0 (4)	C2—C15—H15	116.8
C13—C8—N1	124.2 (5)	C7—N1—C8	124.2 (4)
C10—C9—C8	121.2 (5)	C1—O1—H1	109.5
O1—C1—C2—C3	179.1 (4)	C13—C8—C9—C10	1.5 (7)
C6—C1—C2—C3	−0.6 (7)	N1—C8—C9—C10	−178.8 (4)
O1—C1—C2—C15	0.5 (7)	C13—C8—C9—Cl1	179.0 (3)
C6—C1—C2—C15	−179.2 (4)	N1—C8—C9—Cl1	−1.3 (6)
C1—C2—C3—C4	0.2 (7)	C8—C9—C10—C11	−0.7 (7)
C15—C2—C3—C4	178.9 (4)	Cl1—C9—C10—C11	−178.2 (4)
C2—C3—C4—C5	−0.5 (7)	C9—C10—C11—C12	0.0 (7)
C2—C3—C4—C14	−179.5 (4)	C9—C10—C11—Cl2	179.7 (3)
C3—C4—C5—C6	1.2 (7)	C10—C11—C12—C13	−0.3 (7)
C14—C4—C5—C6	−179.8 (4)	Cl2—C11—C12—C13	−180.0 (4)
C4—C5—C6—C1	−1.5 (7)	C11—C12—C13—C8	1.2 (7)
C4—C5—C6—C7	179.7 (4)	C9—C8—C13—C12	−1.8 (7)
O1—C1—C6—C5	−178.5 (4)	N1—C8—C13—C12	178.5 (4)
C2—C1—C6—C5	1.2 (6)	C3—C2—C15—O2	2.4 (9)
O1—C1—C6—C7	0.3 (7)	C1—C2—C15—O2	−179.0 (5)
C2—C1—C6—C7	180.0 (4)	C6—C7—N1—C8	−178.7 (4)
C5—C6—C7—N1	176.8 (4)	C9—C8—N1—C7	179.7 (4)
C1—C6—C7—N1	−2.0 (7)	C13—C8—N1—C7	−0.6 (7)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.85	2.577 (4)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.85	2.577 (4)	147