1-(4-{[(E)-5-Chloro-2-hy-droxy-benzyl-idene]amino}-phen-yl)ethanone oxime.

The title compound, C(15)H(13)ClN(2)O(2), is an aromatic Schiff base having an aldoxime substituent; the two rings on the azomethine linkage are twisted by 44.4 (1)°. The phenolic H atom is intra-molecularly hydrogen bonded to the azomethine N atom, generating an S(6) ring. In the crystal, inversion dimers linked by pairs of O-H⋯N hydrogen bonds occur. The crystal studied was a non-merohedral twin with a 35% minor component.

Related literature

For background to oxime-type compounds, see: Dong et al. (2009 ▶, 2010b ▶). For the synthesis, see: Rafiq et al. (2008 ▶); Dong et al. (2010a ▶). For the treatment of non-merohedrally twinned diffraction intensities, see: Spek (2009 ▶). We have reported the crystal structure of one of the first examples of a n class="Chemical">Schiff base bearing the oxime unit, see: Zhao et al. (2009 ▶).

Experimental

Crystal data

C15H13ClN2O2

M = 288.72

Monoclinic,

a = 15.356 (2) Å

b = 14.035 (2) Å

c = 6.1124 (6) Å

β = 95.244 (1)°

V = 1311.8 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 293 K

0.40 × 0.10 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.892, T max = 0.986

3689 measured reflections

2971 independent reflections

1552 reflections with I > 2σ(I)

R int = 0.092

Refinement

R[F 2 > 2σ(F 2)] = 0.076

wR(F 2) = 0.239

S = 1.02

2970 reflections

192 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.41 e Å−3

Δρmin = −0.34 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810034586/hg2704sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810034586/hg2704Isup2.hkl

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

C15H13ClN2O2	F(000) = 600
Mr = 288.72	Dx = 1.462 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1371 reflections
a = 15.356 (2) Å	θ = 2.7–24.9°
b = 14.035 (2) Å	µ = 0.29 mm−1
c = 6.1124 (6) Å	T = 293 K
β = 95.244 (1)°	Needle-like, yellow
V = 1311.8 (2) Å3	0.40 × 0.10 × 0.05 mm
Z = 4

Bruker SMART APEX diffractometer	2971 independent reflections
Radiation source: fine-focus sealed tube	1552 reflections with I > 2σ(I)
graphite	Rint = 0.092
φ and ω scans	θmax = 27.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −19→19
Tmin = 0.892, Tmax = 0.986	k = −18→18
3689 measured reflections	l = −2→7

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)] = 0.076	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.239	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.1159P)2] where P = (Fo2 + 2Fc2)/3
2970 reflections	(Δ/σ)max = 0.001
192 parameters	Δρmax = 0.41 e Å−3
2 restraints	Δρmin = −0.34 e Å−3

	x	y	z	Uiso*/Ueq
Cl1	0.26367 (8)	0.34104 (10)	0.2064 (3)	0.0716 (5)
N1	0.6685 (2)	0.3635 (2)	0.1036 (6)	0.0378 (9)
O1	0.5752 (2)	0.4086 (3)	−0.2569 (6)	0.0543 (9)
N2	0.9958 (2)	0.4344 (2)	0.8002 (6)	0.0444 (10)
O2	1.0777 (2)	0.4341 (2)	0.9205 (7)	0.0565 (10)
C1	0.5046 (3)	0.3912 (3)	−0.1470 (8)	0.0395 (11)
C2	0.4222 (3)	0.4095 (3)	−0.2484 (8)	0.0454 (11)
H2A	0.4164	0.4333	−0.3910	0.054*
C3	0.3485 (3)	0.3930 (3)	−0.1418 (9)	0.0481 (12)
H3	0.2933	0.4051	−0.2124	0.058*
C4	0.3566 (3)	0.3589 (3)	0.0678 (9)	0.0421 (11)
C5	0.4378 (3)	0.3407 (3)	0.1758 (8)	0.0407 (10)
H5	0.4424	0.3178	0.3192	0.049*
C6	0.5131 (3)	0.3569 (3)	0.0687 (7)	0.0353 (10)
C7	0.5974 (3)	0.3471 (3)	0.1921 (7)	0.0359 (10)
H7	0.6002	0.3285	0.3386	0.043*
C8	0.7485 (2)	0.3677 (3)	0.2391 (7)	0.0350 (10)
C9	0.8234 (3)	0.3372 (3)	0.1531 (7)	0.0359 (10)
H9	0.8206	0.3124	0.0116	0.043*
C10	0.9030 (3)	0.3438 (3)	0.2787 (8)	0.0368 (10)
H10	0.9531	0.3219	0.2201	0.044*
C11	0.9104 (2)	0.3813 (3)	0.4848 (7)	0.0327 (10)
C12	0.8338 (2)	0.4151 (3)	0.5670 (7)	0.0368 (10)
H12	0.8368	0.4427	0.7058	0.044*
C13	0.7546 (3)	0.4079 (3)	0.4454 (7)	0.0374 (10)
H13	0.7044	0.4304	0.5027	0.045*
C14	0.9956 (3)	0.3880 (3)	0.6196 (8)	0.0363 (10)
C15	1.0748 (3)	0.3417 (3)	0.5426 (9)	0.0524 (13)
H15A	1.1216	0.3436	0.6580	0.079*
H15B	1.0921	0.3752	0.4165	0.079*
H15C	1.0616	0.2767	0.5037	0.079*
H1	0.619 (3)	0.395 (4)	−0.166 (8)	0.10 (2)*
H2	1.076 (4)	0.471 (4)	1.031 (8)	0.12 (3)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0347 (6)	0.0879 (10)	0.0928 (13)	0.0041 (6)	0.0083 (7)	0.0070 (9)
N1	0.0316 (19)	0.0419 (19)	0.039 (2)	0.0017 (14)	−0.0015 (17)	−0.0003 (16)
O1	0.048 (2)	0.075 (2)	0.040 (2)	0.0013 (17)	0.0039 (18)	0.0068 (18)
N2	0.0351 (19)	0.050 (2)	0.045 (3)	−0.0027 (16)	−0.0121 (18)	0.0007 (19)
O2	0.0406 (17)	0.061 (2)	0.064 (3)	0.0004 (15)	−0.0211 (17)	−0.004 (2)
C1	0.037 (2)	0.038 (2)	0.041 (3)	0.0029 (18)	−0.005 (2)	−0.003 (2)
C2	0.050 (3)	0.041 (2)	0.043 (3)	0.006 (2)	−0.014 (2)	−0.001 (2)
C3	0.037 (2)	0.045 (3)	0.059 (4)	0.0054 (19)	−0.011 (2)	−0.005 (2)
C4	0.033 (2)	0.039 (2)	0.053 (3)	0.0005 (17)	−0.001 (2)	−0.005 (2)
C5	0.040 (2)	0.037 (2)	0.044 (3)	0.0021 (18)	−0.004 (2)	−0.002 (2)
C6	0.032 (2)	0.036 (2)	0.037 (3)	−0.0014 (17)	−0.0029 (19)	−0.0036 (19)
C7	0.039 (2)	0.034 (2)	0.033 (2)	0.0015 (17)	−0.004 (2)	−0.0011 (19)
C8	0.032 (2)	0.035 (2)	0.037 (3)	−0.0023 (16)	−0.0002 (19)	0.0018 (19)
C9	0.039 (2)	0.038 (2)	0.030 (2)	−0.0001 (17)	0.0020 (19)	−0.0032 (18)
C10	0.030 (2)	0.039 (2)	0.042 (3)	0.0003 (17)	0.005 (2)	−0.002 (2)
C11	0.028 (2)	0.030 (2)	0.040 (3)	−0.0040 (15)	0.0033 (19)	0.0008 (18)
C12	0.037 (2)	0.043 (2)	0.030 (2)	−0.0021 (18)	−0.0006 (19)	−0.0060 (19)
C13	0.029 (2)	0.046 (2)	0.037 (3)	0.0025 (17)	0.0045 (19)	−0.003 (2)
C14	0.032 (2)	0.033 (2)	0.042 (3)	−0.0031 (17)	−0.002 (2)	0.005 (2)
C15	0.031 (2)	0.066 (3)	0.060 (3)	0.003 (2)	0.005 (2)	−0.005 (3)

Cl1—C4	1.743 (5)	C6—C7	1.444 (6)
N1—C7	1.282 (5)	C7—H7	0.9300
N1—C8	1.419 (5)	C8—C13	1.376 (6)
O1—C1	1.348 (5)	C8—C9	1.375 (5)
O1—H1	0.85 (5)	C9—C10	1.387 (6)
N2—C14	1.281 (6)	C9—H9	0.9300
N2—O2	1.398 (4)	C10—C11	1.360 (6)
O2—H2	0.86 (5)	C10—H10	0.9300
C1—C2	1.382 (6)	C11—C12	1.403 (5)
C1—C6	1.398 (6)	C11—C14	1.484 (5)
C2—C3	1.376 (6)	C12—C13	1.370 (5)
C2—H2A	0.9300	C12—H12	0.9300
C3—C4	1.363 (7)	C13—H13	0.9300
C3—H3	0.9300	C14—C15	1.492 (6)
C4—C5	1.379 (6)	C15—H15A	0.9600
C5—C6	1.400 (6)	C15—H15B	0.9600
C5—H5	0.9300	C15—H15C	0.9600
C7—N1—C8	119.1 (4)	C13—C8—N1	122.3 (4)
C1—O1—H1	104 (4)	C9—C8—N1	118.3 (4)
C14—N2—O2	112.6 (4)	C8—C9—C10	119.6 (4)
N2—O2—H2	109 (5)	C8—C9—H9	120.2
O1—C1—C2	119.2 (4)	C10—C9—H9	120.2
O1—C1—C6	121.5 (4)	C11—C10—C9	122.2 (4)
C2—C1—C6	119.3 (4)	C11—C10—H10	118.9
C3—C2—C1	121.1 (5)	C9—C10—H10	118.9
C3—C2—H2A	119.5	C10—C11—C12	117.4 (4)
C1—C2—H2A	119.5	C10—C11—C14	122.2 (4)
C4—C3—C2	119.7 (4)	C12—C11—C14	120.4 (4)
C4—C3—H3	120.2	C13—C12—C11	120.9 (4)
C2—C3—H3	120.2	C13—C12—H12	119.6
C3—C4—C5	121.1 (4)	C11—C12—H12	119.6
C3—C4—Cl1	119.9 (4)	C12—C13—C8	120.6 (4)
C5—C4—Cl1	119.0 (4)	C12—C13—H13	119.7
C4—C5—C6	119.7 (5)	C8—C13—H13	119.7
C4—C5—H5	120.1	N2—C14—C11	116.3 (4)
C6—C5—H5	120.1	N2—C14—C15	123.7 (4)
C1—C6—C5	119.2 (4)	C11—C14—C15	120.0 (4)
C1—C6—C7	121.8 (4)	C14—C15—H15A	109.5
C5—C6—C7	118.7 (4)	C14—C15—H15B	109.5
N1—C7—C6	121.3 (4)	H15A—C15—H15B	109.5
N1—C7—H7	119.4	C14—C15—H15C	109.5
C6—C7—H7	119.4	H15A—C15—H15C	109.5
C13—C8—C9	119.2 (4)	H15B—C15—H15C	109.5
O1—C1—C2—C3	−179.8 (4)	C7—N1—C8—C9	147.4 (4)
C6—C1—C2—C3	−1.0 (6)	C13—C8—C9—C10	2.7 (6)
C1—C2—C3—C4	0.5 (6)	N1—C8—C9—C10	177.6 (4)
C2—C3—C4—C5	0.2 (7)	C8—C9—C10—C11	−1.2 (6)
C2—C3—C4—Cl1	178.2 (3)	C9—C10—C11—C12	−1.0 (6)
C3—C4—C5—C6	−0.4 (6)	C9—C10—C11—C14	179.8 (4)
Cl1—C4—C5—C6	−178.4 (3)	C10—C11—C12—C13	1.7 (6)
O1—C1—C6—C5	179.6 (4)	C14—C11—C12—C13	−179.0 (4)
C2—C1—C6—C5	0.8 (6)	C11—C12—C13—C8	−0.3 (7)
O1—C1—C6—C7	6.1 (6)	C9—C8—C13—C12	−1.9 (6)
C2—C1—C6—C7	−172.6 (4)	N1—C8—C13—C12	−176.6 (4)
C4—C5—C6—C1	−0.1 (6)	O2—N2—C14—C11	177.7 (3)
C4—C5—C6—C7	173.6 (4)	O2—N2—C14—C15	−1.9 (6)
C8—N1—C7—C6	170.1 (3)	C10—C11—C14—N2	172.3 (4)
C1—C6—C7—N1	−4.7 (6)	C12—C11—C14—N2	−7.0 (6)
C5—C6—C7—N1	−178.2 (3)	C10—C11—C14—C15	−8.1 (6)
C7—N1—C8—C13	−37.9 (6)	C12—C11—C14—C15	172.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.85 (5)	1.81 (3)	2.594 (5)	153 (6)
O2—H2···N2i	0.86 (5)	2.06 (4)	2.819 (5)	147 (6)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.85 (5)	1.81 (3)	2.594 (5)	153 (6)
O2—H2⋯N2i	0.86 (5)	2.06 (4)	2.819 (5)	147 (6)

Symmetry code: (i) .