4-[(E)-(2,3-Dichloro­benzyl­idene)amino]­phenol

Abstract

In the title compound, C₁₃H₉Cl₂NO, the dihedral angle between the benzene rings is 54.22 (10)°. In the crystal, mol­ecules are linked by O—H⋯N inter­molecular hydrogen bonds, forming a zigzag C(7) chain along the a axis.

Related literature

For the biological properties of Schiff base ligands, see: Bedia et al. (2006 ▶). For related structures, see: Fun et al. (2008 ▶); Alhadi et al. (2008 ▶); Nie (2008 ▶). For reference bond-length values, see: Allen et al. (1987 ▶).

Experimental

Crystal data

• C₁₃H₉Cl₂NO

• M _r = 266.11

• Orthorhombic,

• a = 6.049 (4) Å

• b = 10.038 (6) Å

• c = 19.645 (12) Å

• V = 1192.8 (13) ų

• Z = 4

• Mo Kα radiation

• μ = 0.52 mm⁻¹

• T = 296 K

• 0.25 × 0.23 × 0.21 mm

Data collection

• Bruker APEXII CCD diffractometer

• Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T _min = 0.880, T _max = 0.898

• 4853 measured reflections

• 2184 independent reflections

• 1998 reflections with I > 2σ(I)

• R _int = 0.037

Refinement

• R[F ² > 2σ(F ²)] = 0.030

• wR(F ²) = 0.072

• S = 1.17

• 2184 reflections

• 156 parameters

• H-atom parameters constrained

• Δρ_max = 0.15 e Å⁻³

• Δρ_min = −0.14 e Å⁻³

• Absolute structure: Flack (1983 ▶), 869 Friedel pairs

• Flack parameter: 0.04 (6)

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Supplementary material file. DOI: 10.1107/S1600536811019933/hb5895Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1i	0.82	1.99	2.811 (3)	174

Symmetry code: (i) .

supplementary crystallographic information

Comment

Schiff base ligands have received considerable attention during the last decades, mainly because of their structures or for their biological properties (Bedia et al., 2006). We report here the crystal structure of the title new Schiff base compound, (I). In (I) (Fig. 1), the bond lengths and angles are normal and comparable to the values observed in similar compounds (Nie et al., 2008; Fun et al., 2008; Alhadi et al., 2008). The dihedral angle between the two aromatic rings in the Schiff base molecule is 54.22 (10) °, indicating that two these rings are not coplanar. Intermolecular O—H···N hydrogen bonds (Table 1) link the molecules along a axis (Fig. 2).

Experimental

A mixture of 2,3-dichlorobenzaldehyde (5 mmol), 4-aminophenol (5 mmol) and methanol (40 ml) was refluxed for 2 h. It was then allowed to cool and filtered. Recrystallization of the crude product from methanol yielded yellow blocks of (I).

Refinement

H atoms were positioned geometrically and refined using the riding-model approximation, with C—H = 0.93–0.97 Å, O—H = 0.82 Å, and U_iso(H) = 1.2U_eq(C) or U_iso(H) = 1.5U_eq(O).

Figures

Fig. 1.

The molecular structure of the title compounds with 50% probability displacement ellipsoids for non-hydrogen atoms.

Fig. 2.

Molecular packing of the title compound, viewed along the a axis. Hydrogen bonds are shown as dashed lines.

Crystal data

C13H9Cl2NO	F(000) = 544
Mr = 266.11	Dx = 1.482 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2869 reflections
a = 6.049 (4) Å	θ = 2.3–27.2°
b = 10.038 (6) Å	µ = 0.52 mm−1
c = 19.645 (12) Å	T = 296 K
V = 1192.8 (13) Å3	Block, yellow
Z = 4	0.25 × 0.23 × 0.21 mm

Data collection

Bruker APEXII CCD diffractometer	2184 independent reflections
Radiation source: fine-focus sealed tube	1998 reflections with I > 2σ(I)
graphite	Rint = 0.037
φ and ω scans	θmax = 25.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −7→7
Tmin = 0.880, Tmax = 0.898	k = −8→12
4853 measured reflections	l = −23→21

Refinement

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.030	w = 1/[σ2(Fo2) + (0.0269P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.072	(Δ/σ)max < 0.001
S = 1.17	Δρmax = 0.15 e Å−3
2184 reflections	Δρmin = −0.14 e Å−3
156 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.073 (4)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 869 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.04 (6)

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
C1	0.6782 (4)	0.13161 (18)	0.30064 (9)	0.0315 (5)
C2	0.8717 (4)	0.2032 (2)	0.29247 (10)	0.0380 (5)
H2	0.9883	0.1903	0.3226	0.046*
C3	0.8932 (4)	0.2937 (2)	0.23991 (10)	0.0353 (5)
H3	1.0241	0.3413	0.2347	0.042*
C4	0.7192 (3)	0.31355 (18)	0.19496 (10)	0.0305 (5)
C5	0.5261 (4)	0.2441 (2)	0.20450 (11)	0.0389 (5)
H5	0.4074	0.2593	0.1754	0.047*
C6	0.5046 (4)	0.1522 (2)	0.25642 (11)	0.0380 (5)
H6	0.3739	0.1045	0.2615	0.046*
C7	0.9040 (4)	0.3995 (2)	0.10174 (10)	0.0305 (5)
H7	1.0160	0.3406	0.1138	0.037*
C8	0.9356 (3)	0.48183 (19)	0.04113 (10)	0.0302 (5)
C9	0.7862 (4)	0.5815 (2)	0.02412 (11)	0.0404 (5)
H9	0.6685	0.5997	0.0531	0.049*
C10	0.8097 (4)	0.6539 (2)	−0.03507 (13)	0.0528 (6)
H10	0.7081	0.7203	−0.0457	0.063*
C11	0.9837 (5)	0.6281 (2)	−0.07860 (12)	0.0502 (6)
H11	0.9987	0.6761	−0.1188	0.060*
C12	1.1338 (4)	0.5315 (2)	−0.06226 (10)	0.0392 (5)
C13	1.1149 (4)	0.45927 (17)	−0.00259 (10)	0.0317 (5)
Cl1	1.35264 (12)	0.50375 (7)	−0.11774 (3)	0.0628 (2)
Cl2	1.31056 (9)	0.33967 (5)	0.01639 (3)	0.04412 (18)
N1	0.7322 (3)	0.40395 (17)	0.13882 (8)	0.0321 (4)
O1	0.6681 (3)	0.04560 (15)	0.35434 (8)	0.0447 (4)
H1	0.5510	0.0045	0.3531	0.067*

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
C1	0.0295 (12)	0.0359 (10)	0.0290 (10)	−0.0003 (9)	0.0016 (9)	0.0003 (8)
C2	0.0288 (12)	0.0525 (12)	0.0326 (11)	−0.0050 (10)	−0.0052 (9)	0.0053 (9)
C3	0.0249 (12)	0.0454 (12)	0.0355 (11)	−0.0058 (10)	0.0016 (9)	0.0011 (9)
C4	0.0271 (12)	0.0343 (10)	0.0302 (10)	0.0027 (9)	0.0046 (8)	0.0020 (8)
C5	0.0230 (12)	0.0556 (14)	0.0382 (12)	0.0002 (10)	−0.0027 (10)	0.0068 (10)
C6	0.0241 (11)	0.0480 (12)	0.0419 (12)	−0.0102 (11)	0.0010 (9)	0.0070 (10)
C7	0.0270 (11)	0.0325 (10)	0.0319 (11)	0.0014 (9)	−0.0015 (9)	0.0009 (8)
C8	0.0271 (11)	0.0311 (10)	0.0323 (10)	−0.0043 (9)	−0.0019 (8)	−0.0004 (8)
C9	0.0368 (13)	0.0421 (11)	0.0424 (12)	0.0024 (10)	0.0006 (11)	0.0075 (10)
C10	0.0516 (16)	0.0468 (13)	0.0601 (15)	0.0043 (13)	−0.0085 (13)	0.0184 (12)
C11	0.0582 (17)	0.0521 (14)	0.0403 (13)	−0.0114 (13)	−0.0060 (12)	0.0166 (11)
C12	0.0396 (14)	0.0467 (12)	0.0312 (11)	−0.0145 (11)	0.0007 (10)	−0.0038 (9)
C13	0.0323 (12)	0.0321 (10)	0.0309 (11)	−0.0072 (8)	−0.0015 (9)	−0.0021 (8)
Cl1	0.0631 (5)	0.0830 (5)	0.0424 (4)	−0.0188 (4)	0.0200 (3)	−0.0021 (3)
Cl2	0.0381 (3)	0.0505 (3)	0.0437 (3)	0.0092 (3)	0.0070 (3)	−0.0034 (2)
N1	0.0269 (10)	0.0360 (9)	0.0334 (9)	0.0021 (7)	0.0006 (8)	0.0007 (7)
O1	0.0372 (10)	0.0563 (9)	0.0407 (8)	−0.0109 (8)	−0.0033 (7)	0.0166 (7)

Geometric parameters (Å, °)

C1—O1	1.365 (2)	C7—H7	0.9300
C1—C6	1.379 (3)	C8—C9	1.390 (3)
C1—C2	1.382 (3)	C8—C13	1.402 (3)
C2—C3	1.382 (3)	C9—C10	1.378 (3)
C2—H2	0.9300	C9—H9	0.9300
C3—C4	1.388 (3)	C10—C11	1.381 (4)
C3—H3	0.9300	C10—H10	0.9300
C4—C5	1.373 (3)	C11—C12	1.366 (3)
C4—N1	1.430 (2)	C11—H11	0.9300
C5—C6	1.381 (3)	C12—C13	1.383 (3)
C5—H5	0.9300	C12—Cl1	1.737 (2)
C6—H6	0.9300	C13—Cl2	1.727 (2)
C7—N1	1.270 (3)	O1—H1	0.8200
C7—C8	1.462 (3)
O1—C1—C6	123.22 (19)	C9—C8—C13	118.18 (19)
O1—C1—C2	117.18 (18)	C9—C8—C7	121.20 (19)
C6—C1—C2	119.58 (18)	C13—C8—C7	120.60 (18)
C3—C2—C1	120.57 (19)	C10—C9—C8	121.0 (2)
C3—C2—H2	119.7	C10—C9—H9	119.5
C1—C2—H2	119.7	C8—C9—H9	119.5
C2—C3—C4	119.86 (19)	C9—C10—C11	120.1 (2)
C2—C3—H3	120.1	C9—C10—H10	119.9
C4—C3—H3	120.1	C11—C10—H10	119.9
C5—C4—C3	119.06 (18)	C12—C11—C10	119.6 (2)
C5—C4—N1	118.29 (18)	C12—C11—H11	120.2
C3—C4—N1	122.66 (17)	C10—C11—H11	120.2
C4—C5—C6	121.3 (2)	C11—C12—C13	121.1 (2)
C4—C5—H5	119.3	C11—C12—Cl1	118.21 (17)
C6—C5—H5	119.3	C13—C12—Cl1	120.71 (18)
C1—C6—C5	119.6 (2)	C12—C13—C8	119.9 (2)
C1—C6—H6	120.2	C12—C13—Cl2	119.40 (17)
C5—C6—H6	120.2	C8—C13—Cl2	120.68 (15)
N1—C7—C8	123.66 (19)	C7—N1—C4	117.70 (17)
N1—C7—H7	118.2	C1—O1—H1	109.5
C8—C7—H7	118.2
O1—C1—C2—C3	−179.00 (19)	C9—C10—C11—C12	−0.8 (4)
C6—C1—C2—C3	−0.8 (3)	C10—C11—C12—C13	−0.2 (3)
C1—C2—C3—C4	0.2 (3)	C10—C11—C12—Cl1	−179.07 (19)
C2—C3—C4—C5	1.3 (3)	C11—C12—C13—C8	2.0 (3)
C2—C3—C4—N1	−178.85 (18)	Cl1—C12—C13—C8	−179.16 (15)
C3—C4—C5—C6	−2.1 (3)	C11—C12—C13—Cl2	−179.20 (17)
N1—C4—C5—C6	177.97 (19)	Cl1—C12—C13—Cl2	−0.4 (2)
O1—C1—C6—C5	178.0 (2)	C9—C8—C13—C12	−2.8 (3)
C2—C1—C6—C5	0.0 (3)	C7—C8—C13—C12	175.34 (18)
C4—C5—C6—C1	1.5 (3)	C9—C8—C13—Cl2	178.46 (15)
N1—C7—C8—C9	6.8 (3)	C7—C8—C13—Cl2	−3.4 (3)
N1—C7—C8—C13	−171.26 (19)	C8—C7—N1—C4	177.33 (18)
C13—C8—C9—C10	1.8 (3)	C5—C4—N1—C7	−133.5 (2)
C7—C8—C9—C10	−176.3 (2)	C3—C4—N1—C7	46.7 (3)
C8—C9—C10—C11	−0.1 (4)

Hydrogen-bond geometry (Å, °)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1i	0.82	1.99	2.811 (3)	174

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