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

Sun, L.-X.; Yu, Y.-D.; Wei, G.-Y.

doi:10.1107/S1600536811019933

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1564

doi:10.1107/S1600536811019933

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

Li-Xia Sun,^a Yun-Dan Yu ^a and Guo-Ying Wei ^a ^*

^aCollege of Materials Science & Engineering, China Jiliang University, Hangzhou 310018, People's Republic of China
^*Correspondence e-mail: nanocrystal11@163.com

(Received 25 May 2011; accepted 25 May 2011; online 4 June 2011)

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, P 2₁ 2₁ 2₁
a = 6.049 (4) Å
b = 10.038 (6) Å
c = 19.645 (12) Å
V = 1192.8 (13) Å³
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[F² > 2σ(F²)] = 0.030
wR(F²) = 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)

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) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811019933/hb5895sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811019933/hb5895Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811019933/hb5895Isup3.cml

checkCIF report

Comment top

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).

Related literature top

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 top

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).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 (Sheldrick, 2008).

Figures top

	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.

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

Crystal data top

C₁₃H₉Cl₂NO	F(000) = 544
M_r = 266.11	D_x = 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 top

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

Refinement top

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(F_o²) + (0.0269P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.072	(Δ/σ)_max < 0.001
S = 1.17	Δρ_max = 0.15 e Å⁻³
2184 reflections	Δρ_min = −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	Absolute structure parameter: 0.04 (6)

Crystal data top

C₁₃H₉Cl₂NO	V = 1192.8 (13) Å³
M_r = 266.11	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 6.049 (4) Å	µ = 0.52 mm⁻¹
b = 10.038 (6) Å	T = 296 K
c = 19.645 (12) Å	0.25 × 0.23 × 0.21 mm

Data collection top

Bruker APEXII CCD diffractometer	2184 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	1998 reflections with I > 2σ(I)
T_min = 0.880, T_max = 0.898	R_int = 0.037
4853 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	H-atom parameters constrained
wR(F²) = 0.072	Δρ_max = 0.15 e Å⁻³
S = 1.17	Δρ_min = −0.14 e Å⁻³
2184 reflections	Absolute structure: Flack (1983), 869 Friedel pairs
156 parameters	Absolute structure parameter: 0.04 (6)
0 restraints

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
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 (Å²) top

	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, º) top

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, º) top

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) −x+1, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₉Cl₂NO
M_r	266.11
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	296
a, b, c (Å)	6.049 (4), 10.038 (6), 19.645 (12)
V (Å³)	1192.8 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.52
Crystal size (mm)	0.25 × 0.23 × 0.21

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.880, 0.898
No. of measured, independent and observed [I > 2σ(I)] reflections	4853, 2184, 1998
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.072, 1.17
No. of reflections	2184
No. of parameters	156
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.14
Absolute structure	Flack (1983), 869 Friedel pairs
Absolute structure parameter	0.04 (6)

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) −x+1, y−1/2, −z+1/2.

Acknowledgements

This project was supported by the Zhejiang Provincial Natural Science Foundation of China (grant No. Y4110290).

References

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