4-Chloro-2-((E)-{3-[1-(hydroxy-imino)eth-yl]phen-yl}imino-meth-yl)phenol.

The title compound, C(15)H(13)ClN(2)O(2), adopts an E conformation with respect to the azomethine C=N bond. The aniline and phenol rings are almost coplanar, making a dihedral angle of 3.33 (2)°. In the crystal, the mol-ecules lie about inversion centers, forming dimers that are connected by inter-molecular O-H⋯N hydrogen bonds, resulting in six-membered rings with graph-set motif R(2) (2)(6). In addition, there is a strong inter-molecular O-H⋯N hydrogen-bonding inter-action, resulting in an S(6) ring motif. Weak π-π inter-actions between the benzene rings [centroid-centroid distance = 3.809 (1) Å] further stabilize the crystal structure.

Related literature

For background to Schiff bases, see: Dong et al. (2007 ▶, 2008 ▶, 2009 ▶); Eltayeb et al. (2008 ▶). For related crystal strcutures, see: Butcher et al. (2005 ▶); Golovnia et al. (2009 ▶); Xu et al. (2008 ▶); Rafiq et al. (2008 ▶); Zhao et al. (2009 ▶).

Experimental

Crystal data

C15H13ClN2O2

M = 288.72

Monoclinic,

a = 16.7139 (16) Å

b = 5.9983 (6) Å

c = 13.3902 (11) Å

β = 96.328 (2)°

V = 1334.3 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 298 K

0.40 × 0.12 × 0.07 mm

Data collection

Siemens SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.893, T max = 0.980

6410 measured reflections

2349 independent reflections

1398 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.092

S = 1.04

2349 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.18 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809045942/pv2220sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809045942/pv2220Isup2.hkl

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

C15H13ClN2O2	F(000) = 600
Mr = 288.72	Dx = 1.437 Mg m−3
Monoclinic, P21/c	Melting point = 454–456 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 16.7139 (16) Å	Cell parameters from 1148 reflections
b = 5.9983 (6) Å	θ = 3.1–25.3°
c = 13.3902 (11) Å	µ = 0.29 mm−1
β = 96.328 (2)°	T = 298 K
V = 1334.3 (2) Å3	Needle, yellow
Z = 4	0.40 × 0.12 × 0.07 mm

Siemens SMART 1000 CCD area-detector diffractometer	2349 independent reflections
Radiation source: fine-focus sealed tube	1398 reflections with I > 2σ(I)
graphite	Rint = 0.053
φ and ω scans	θmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→19
Tmin = 0.893, Tmax = 0.980	k = −7→7
6410 measured reflections	l = −15→11

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0246P)2] where P = (Fo2 + 2Fc2)/3
2349 reflections	(Δ/σ)max < 0.001
182 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

Experimental. m. p. 454–456 K. Anal. Calc.: C, 62.40; H, 4.54; N, 9.70. Found: C, 62.10; H, 4.59; N, 9.89.

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	0.47005 (4)	−0.34472 (13)	0.16802 (5)	0.0679 (3)
N1	0.04965 (12)	1.3024 (4)	−0.03178 (14)	0.0492 (6)
N2	0.25468 (11)	0.4873 (4)	0.02923 (14)	0.0459 (5)
O1	0.01107 (10)	1.4271 (3)	−0.11173 (11)	0.0660 (6)
H1	−0.0105	1.5364	−0.0895	0.099*
O2	0.29783 (10)	0.2627 (3)	−0.12216 (12)	0.0714 (6)
H2	0.2760	0.3628	−0.0934	0.107*
C1	0.08207 (16)	1.0646 (5)	−0.16879 (17)	0.0649 (9)
H1A	0.0436	1.1557	−0.2087	0.097*
H1B	0.0670	0.9107	−0.1768	0.097*
H1C	0.1344	1.0862	−0.1903	0.097*
C2	0.08394 (13)	1.1288 (4)	−0.06072 (16)	0.0397 (6)
C3	0.12822 (12)	0.9899 (4)	0.01858 (16)	0.0368 (6)
C4	0.16997 (12)	0.8025 (4)	−0.00603 (17)	0.0414 (6)
H4	0.1693	0.7636	−0.0734	0.050*
C5	0.21285 (13)	0.6705 (4)	0.06599 (18)	0.0403 (6)
C6	0.21285 (14)	0.7264 (5)	0.16624 (18)	0.0512 (7)
H6	0.2406	0.6389	0.2159	0.061*
C7	0.17157 (15)	0.9121 (5)	0.19178 (18)	0.0552 (8)
H7	0.1719	0.9499	0.2592	0.066*
C8	0.12969 (14)	1.0435 (4)	0.11943 (17)	0.0465 (7)
H8	0.1023	1.1688	0.1384	0.056*
C9	0.29415 (13)	0.3476 (4)	0.08762 (19)	0.0462 (7)
H9	0.2948	0.3651	0.1567	0.055*
C10	0.33755 (13)	0.1644 (4)	0.04994 (18)	0.0410 (6)
C11	0.33784 (14)	0.1268 (5)	−0.05337 (19)	0.0491 (7)
C12	0.37878 (14)	−0.0525 (5)	−0.08613 (19)	0.0572 (8)
H12	0.3789	−0.0767	−0.1547	0.069*
C13	0.41961 (14)	−0.1967 (5)	−0.0189 (2)	0.0547 (7)
H13	0.4473	−0.3176	−0.0417	0.066*
C14	0.41926 (13)	−0.1606 (4)	0.08297 (19)	0.0459 (7)
C15	0.37940 (13)	0.0169 (4)	0.11697 (18)	0.0462 (7)
H15	0.3801	0.0399	0.1857	0.055*

	U11	U22	U33	U12	U13	U23
Cl1	0.0726 (5)	0.0574 (5)	0.0723 (5)	0.0192 (4)	0.0021 (4)	0.0118 (4)
N1	0.0631 (13)	0.0413 (15)	0.0398 (12)	0.0115 (12)	−0.0090 (11)	0.0044 (11)
N2	0.0427 (12)	0.0397 (15)	0.0543 (13)	0.0036 (11)	0.0008 (10)	0.0030 (11)
O1	0.0957 (14)	0.0518 (14)	0.0464 (11)	0.0267 (11)	−0.0102 (10)	0.0062 (9)
O2	0.0864 (13)	0.0763 (16)	0.0495 (11)	0.0282 (12)	−0.0015 (10)	0.0080 (10)
C1	0.086 (2)	0.070 (2)	0.0373 (15)	0.0267 (17)	0.0000 (15)	0.0016 (14)
C2	0.0442 (14)	0.0391 (17)	0.0347 (14)	0.0009 (13)	−0.0003 (12)	0.0000 (12)
C3	0.0392 (13)	0.0343 (17)	0.0363 (14)	−0.0022 (12)	0.0019 (11)	0.0010 (12)
C4	0.0453 (14)	0.0431 (18)	0.0346 (13)	−0.0041 (13)	−0.0005 (12)	−0.0007 (12)
C5	0.0395 (14)	0.0344 (16)	0.0465 (16)	−0.0016 (12)	0.0023 (12)	0.0040 (13)
C6	0.0591 (16)	0.050 (2)	0.0437 (16)	0.0102 (14)	0.0013 (13)	0.0107 (13)
C7	0.0703 (18)	0.060 (2)	0.0348 (15)	0.0112 (16)	0.0026 (14)	0.0027 (14)
C8	0.0553 (15)	0.0440 (18)	0.0404 (15)	0.0106 (13)	0.0060 (13)	0.0005 (13)
C9	0.0453 (15)	0.0417 (18)	0.0503 (15)	−0.0006 (14)	0.0000 (13)	−0.0003 (13)
C10	0.0378 (13)	0.0352 (16)	0.0495 (16)	−0.0004 (12)	0.0019 (12)	−0.0013 (13)
C11	0.0448 (15)	0.054 (2)	0.0474 (17)	0.0058 (14)	−0.0004 (13)	0.0054 (14)
C12	0.0594 (17)	0.068 (2)	0.0447 (16)	0.0077 (16)	0.0070 (14)	−0.0040 (15)
C13	0.0473 (15)	0.053 (2)	0.0645 (19)	0.0076 (14)	0.0098 (15)	−0.0063 (15)
C14	0.0397 (14)	0.0403 (18)	0.0567 (17)	0.0044 (13)	0.0009 (13)	0.0048 (14)
C15	0.0425 (14)	0.0480 (19)	0.0465 (15)	−0.0007 (13)	−0.0016 (12)	0.0002 (13)

Cl1—C14	1.739 (2)	C5—C6	1.384 (3)
N1—C2	1.269 (3)	C6—C7	1.373 (3)
N1—O1	1.403 (2)	C6—H6	0.9300
N2—C9	1.279 (3)	C7—C8	1.379 (3)
N2—C5	1.419 (3)	C7—H7	0.9300
O1—H1	0.8200	C8—H8	0.9300
O2—C11	1.351 (3)	C9—C10	1.439 (3)
O2—H2	0.8200	C9—H9	0.9300
C1—C2	1.495 (3)	C10—C15	1.393 (3)
C1—H1A	0.9600	C10—C11	1.402 (3)
C1—H1B	0.9600	C11—C12	1.372 (3)
C1—H1C	0.9600	C12—C13	1.375 (3)
C2—C3	1.482 (3)	C12—H12	0.9300
C3—C4	1.382 (3)	C13—C14	1.381 (3)
C3—C8	1.386 (3)	C13—H13	0.9300
C4—C5	1.385 (3)	C14—C15	1.361 (3)
C4—H4	0.9300	C15—H15	0.9300
C2—N1—O1	112.91 (19)	C6—C7—H7	119.4
C9—N2—C5	122.4 (2)	C8—C7—H7	119.4
N1—O1—H1	109.5	C7—C8—C3	120.3 (2)
C11—O2—H2	109.5	C7—C8—H8	119.8
C2—C1—H1A	109.5	C3—C8—H8	119.8
C2—C1—H1B	109.5	N2—C9—C10	122.2 (2)
H1A—C1—H1B	109.5	N2—C9—H9	118.9
C2—C1—H1C	109.5	C10—C9—H9	118.9
H1A—C1—H1C	109.5	C15—C10—C11	118.5 (2)
H1B—C1—H1C	109.5	C15—C10—C9	119.8 (2)
N1—C2—C3	116.7 (2)	C11—C10—C9	121.7 (2)
N1—C2—C1	123.0 (2)	O2—C11—C12	118.8 (2)
C3—C2—C1	120.3 (2)	O2—C11—C10	121.4 (2)
C4—C3—C8	117.8 (2)	C12—C11—C10	119.8 (2)
C4—C3—C2	120.8 (2)	C11—C12—C13	120.8 (2)
C8—C3—C2	121.4 (2)	C11—C12—H12	119.6
C3—C4—C5	122.4 (2)	C13—C12—H12	119.6
C3—C4—H4	118.8	C12—C13—C14	119.5 (3)
C5—C4—H4	118.8	C12—C13—H13	120.3
C6—C5—C4	118.8 (2)	C14—C13—H13	120.3
C6—C5—N2	125.2 (2)	C15—C14—C13	120.6 (2)
C4—C5—N2	116.0 (2)	C15—C14—Cl1	120.0 (2)
C7—C6—C5	119.5 (2)	C13—C14—Cl1	119.5 (2)
C7—C6—H6	120.3	C14—C15—C10	120.7 (2)
C5—C6—H6	120.3	C14—C15—H15	119.6
C6—C7—C8	121.3 (2)	C10—C15—H15	119.6
O1—N1—C2—C3	178.37 (18)	C2—C3—C8—C7	−179.7 (2)
O1—N1—C2—C1	−0.7 (3)	C5—N2—C9—C10	−178.9 (2)
N1—C2—C3—C4	−177.5 (2)	N2—C9—C10—C15	−179.8 (2)
C1—C2—C3—C4	1.6 (3)	N2—C9—C10—C11	−1.0 (4)
N1—C2—C3—C8	2.1 (3)	C15—C10—C11—O2	179.4 (2)
C1—C2—C3—C8	−178.8 (2)	C9—C10—C11—O2	0.6 (4)
C8—C3—C4—C5	−0.5 (3)	C15—C10—C11—C12	0.1 (4)
C2—C3—C4—C5	179.1 (2)	C9—C10—C11—C12	−178.8 (2)
C3—C4—C5—C6	1.0 (3)	O2—C11—C12—C13	−179.3 (2)
C3—C4—C5—N2	−178.2 (2)	C10—C11—C12—C13	0.1 (4)
C9—N2—C5—C6	3.5 (4)	C11—C12—C13—C14	0.1 (4)
C9—N2—C5—C4	−177.4 (2)	C12—C13—C14—C15	−0.5 (4)
C4—C5—C6—C7	−0.9 (4)	C12—C13—C14—Cl1	179.35 (19)
N2—C5—C6—C7	178.2 (2)	C13—C14—C15—C10	0.6 (4)
C5—C6—C7—C8	0.3 (4)	Cl1—C14—C15—C10	−179.18 (17)
C6—C7—C8—C3	0.2 (4)	C11—C10—C15—C14	−0.4 (4)
C4—C3—C8—C7	−0.1 (3)	C9—C10—C15—C14	178.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N2	0.82	1.87	2.601 (3)	147
O1—H1···N1i	0.82	2.06	2.789 (3)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N2	0.82	1.87	2.601 (3)	147
O1—H1⋯N1i	0.82	2.06	2.789 (3)	149

Symmetry code: (i) .