Crystal structure of 3-{(E)-[(3,4-di-chloro-phen-yl)imino]-meth-yl}benzene-1,2-diol.

In the title Schiff base, C13H9Cl2NO2, which arose from the condensation of 3,4-di-chloro-aniline with 2,3-di-hydroxy-benzaldehyde, the dihedral angle between the aromatic rings is 44.74 (13)°. Intra-molecular O-H⋯O and O-H⋯N hydrogen bonds close S(5) and S(6) rings, respectively. In the crystal, inversion dimers linked by pairs of O-H⋯O hydrogen bonds generate R 2 (2)(10) loops. A weak C-H⋯π inter-action is also observed.

Related literature

For related structures, see: Fun et al. (2011 ▸); Keleşoğlu et al. (2009 ▸); Shuja et al. (2006 ▸); Tahir et al. (2012 ▸); Temel et al. (2007 ▸).

Experimental

Crystal data

C13H9Cl2NO2

M = 282.11

Triclinic,

a = 6.4237 (8) Å

b = 8.8412 (11) Å

c = 11.7799 (15) Å

α = 88.606 (6)°

β = 76.588 (6)°

γ = 70.193 (5)°

V = 611.20 (13) Å3

Z = 2

Mo Kα radiation

μ = 0.52 mm−1

T = 296 K

0.34 × 0.26 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▸) T min = 0.844, T max = 0.902

8896 measured reflections

2671 independent reflections

1866 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.164

S = 1.04

2671 reflections

165 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.33 e Å−3

Data collection: APEX2 (Bruker, 2007 ▸); cell refinement: SAINT (Bruker, 2007 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸) and PLATON (Spek, 2009 ▸); software used to prepare material for publication: WinGX (Farrugia, 2012 ▸) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015001401/hb7353sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015001401/hb7353Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015001401/hb7353Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015001401/hb7353fig1.tif

View of the title compound with displacement ellipsoids drawn at the 50% probability level.

Click here for additional data file.

PLATON . DOI: 10.1107/S2056989015001401/hb7353fig2.tif

The partial packing (PLATON; Spek, 2009), which shows that mol­ecules form dimers due to O—H⋯O inter­actions.

CCDC reference: 1044861

Additional supporting information: crystallographic information; 3D view; checkCIF report

C13H9Cl2NO2	Z = 2
Mr = 282.11	F(000) = 284
Triclinic, P1	Dx = 1.533 Mg m−3
a = 6.4237 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.8412 (11) Å	Cell parameters from 1866 reflections
c = 11.7799 (15) Å	θ = 1.8–27.0°
α = 88.606 (6)°	µ = 0.52 mm−1
β = 76.588 (6)°	T = 296 K
γ = 70.193 (5)°	Prism, red
V = 611.20 (13) Å3	0.34 × 0.26 × 0.20 mm

Bruker Kappa APEXII CCD diffractometer	2671 independent reflections
Radiation source: fine-focus sealed tube	1866 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
Detector resolution: 7.80 pixels mm-1	θmax = 27.0°, θmin = 1.8°
ω scans	h = −8→7
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −11→9
Tmin = 0.844, Tmax = 0.902	l = −14→15
8896 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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.164	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0781P)2 + 0.3755P] where P = (Fo2 + 2Fc2)/3
2671 reflections	(Δ/σ)max < 0.001
165 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.32 e Å−3

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	0.24642 (15)	0.26936 (10)	0.01956 (8)	0.0657 (3)
Cl2	0.73742 (15)	0.11968 (10)	0.06575 (9)	0.0707 (3)
O1	−0.2559 (3)	0.9592 (2)	0.38833 (19)	0.0508 (5)
H1	−0.1671	0.8794	0.3473	0.076*
O2	−0.4973 (3)	1.2453 (3)	0.5138 (2)	0.0594 (6)
H2	−0.5353	1.1679	0.5037	0.089*
N1	0.1345 (4)	0.7735 (3)	0.2617 (2)	0.0452 (6)
C1	−0.1526 (5)	1.0707 (3)	0.3887 (2)	0.0388 (6)
C2	−0.2793 (5)	1.2167 (3)	0.4525 (2)	0.0440 (6)
C3	−0.1834 (5)	1.3338 (3)	0.4543 (2)	0.0478 (7)
H3	−0.2694	1.4313	0.4964	0.057*
C4	0.0401 (5)	1.3083 (4)	0.3943 (3)	0.0516 (7)
H4	0.1030	1.3886	0.3954	0.062*
C5	0.1694 (5)	1.1613 (4)	0.3322 (3)	0.0494 (7)
H5	0.3201	1.1427	0.2932	0.059*
C6	0.0738 (5)	1.0419 (3)	0.3285 (2)	0.0409 (6)
C7	0.2124 (5)	0.8875 (3)	0.2674 (2)	0.0440 (6)
H7	0.3638	0.8708	0.2309	0.053*
C8	0.2859 (5)	0.6190 (3)	0.2123 (2)	0.0433 (6)
C9	0.2070 (5)	0.5315 (3)	0.1462 (2)	0.0464 (7)
H9	0.0614	0.5751	0.1334	0.056*
C10	0.3479 (5)	0.3784 (3)	0.0998 (2)	0.0447 (6)
C11	0.5634 (5)	0.3123 (3)	0.1205 (2)	0.0471 (7)
C12	0.6396 (5)	0.3969 (4)	0.1879 (3)	0.0490 (7)
H12	0.7834	0.3514	0.2027	0.059*
C13	0.5000 (5)	0.5513 (3)	0.2339 (2)	0.0480 (7)
H13	0.5511	0.6091	0.2793	0.058*

	U11	U22	U33	U12	U13	U23
Cl1	0.0749 (6)	0.0607 (5)	0.0663 (5)	−0.0278 (4)	−0.0167 (4)	−0.0188 (4)
Cl2	0.0675 (6)	0.0459 (5)	0.0815 (6)	−0.0049 (4)	−0.0040 (4)	−0.0243 (4)
O1	0.0505 (11)	0.0377 (10)	0.0591 (13)	−0.0162 (9)	0.0005 (9)	−0.0157 (9)
O2	0.0502 (12)	0.0463 (12)	0.0765 (15)	−0.0184 (10)	0.0001 (11)	−0.0216 (11)
N1	0.0488 (13)	0.0387 (12)	0.0405 (12)	−0.0089 (10)	−0.0041 (10)	−0.0057 (10)
C1	0.0451 (14)	0.0348 (13)	0.0361 (13)	−0.0133 (11)	−0.0086 (11)	−0.0023 (10)
C2	0.0503 (16)	0.0365 (14)	0.0419 (14)	−0.0111 (12)	−0.0094 (12)	−0.0072 (11)
C3	0.0619 (18)	0.0362 (14)	0.0423 (15)	−0.0117 (13)	−0.0133 (13)	−0.0077 (12)
C4	0.067 (2)	0.0455 (16)	0.0519 (17)	−0.0291 (15)	−0.0173 (15)	0.0016 (13)
C5	0.0536 (17)	0.0495 (16)	0.0469 (16)	−0.0240 (14)	−0.0058 (13)	−0.0009 (13)
C6	0.0489 (15)	0.0346 (13)	0.0355 (13)	−0.0114 (12)	−0.0070 (11)	−0.0001 (11)
C7	0.0473 (15)	0.0405 (14)	0.0372 (14)	−0.0113 (12)	−0.0016 (11)	−0.0053 (11)
C8	0.0508 (16)	0.0365 (14)	0.0359 (14)	−0.0124 (12)	−0.0007 (12)	−0.0059 (11)
C9	0.0490 (16)	0.0435 (15)	0.0442 (15)	−0.0146 (13)	−0.0073 (12)	−0.0045 (12)
C10	0.0531 (16)	0.0436 (15)	0.0373 (14)	−0.0198 (13)	−0.0051 (12)	−0.0047 (11)
C11	0.0524 (16)	0.0396 (14)	0.0406 (15)	−0.0113 (13)	0.0001 (12)	−0.0070 (12)
C12	0.0469 (16)	0.0486 (16)	0.0463 (16)	−0.0102 (13)	−0.0094 (13)	−0.0060 (13)
C13	0.0546 (17)	0.0455 (16)	0.0422 (15)	−0.0160 (13)	−0.0089 (13)	−0.0103 (12)

Cl1—C10	1.733 (3)	C4—H4	0.9300
Cl2—C11	1.731 (3)	C5—C6	1.396 (4)
O1—C1	1.363 (3)	C5—H5	0.9300
O1—H1	0.8200	C6—C7	1.450 (4)
O2—C2	1.359 (3)	C7—H7	0.9300
O2—H2	0.8200	C8—C13	1.383 (4)
N1—C7	1.277 (4)	C8—C9	1.392 (4)
N1—C8	1.423 (3)	C9—C10	1.388 (4)
C1—C2	1.394 (4)	C9—H9	0.9300
C1—C6	1.401 (4)	C10—C11	1.385 (4)
C2—C3	1.375 (4)	C11—C12	1.373 (4)
C3—C4	1.390 (4)	C12—C13	1.394 (4)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.395 (4)	C13—H13	0.9300
C1—O1—H1	109.5	N1—C7—C6	122.5 (3)
C2—O2—H2	109.5	N1—C7—H7	118.7
C7—N1—C8	119.6 (2)	C6—C7—H7	118.7
O1—C1—C2	117.8 (2)	C13—C8—C9	119.9 (2)
O1—C1—C6	122.1 (2)	C13—C8—N1	122.1 (3)
C2—C1—C6	120.1 (2)	C9—C8—N1	117.9 (3)
O2—C2—C3	119.1 (2)	C10—C9—C8	119.3 (3)
O2—C2—C1	120.9 (2)	C10—C9—H9	120.3
C3—C2—C1	120.0 (3)	C8—C9—H9	120.3
C2—C3—C4	120.9 (3)	C11—C10—C9	120.3 (3)
C2—C3—H3	119.6	C11—C10—Cl1	120.7 (2)
C4—C3—H3	119.6	C9—C10—Cl1	118.9 (2)
C3—C4—C5	119.5 (3)	C12—C11—C10	120.5 (3)
C3—C4—H4	120.3	C12—C11—Cl2	118.9 (2)
C5—C4—H4	120.3	C10—C11—Cl2	120.6 (2)
C4—C5—C6	120.3 (3)	C11—C12—C13	119.5 (3)
C4—C5—H5	119.8	C11—C12—H12	120.2
C6—C5—H5	119.8	C13—C12—H12	120.2
C5—C6—C1	119.3 (2)	C8—C13—C12	120.4 (3)
C5—C6—C7	119.8 (3)	C8—C13—H13	119.8
C1—C6—C7	120.9 (2)	C12—C13—H13	119.8
O1—C1—C2—O2	1.1 (4)	C1—C6—C7—N1	2.5 (4)
C6—C1—C2—O2	−178.3 (3)	C7—N1—C8—C13	40.5 (4)
O1—C1—C2—C3	−179.2 (3)	C7—N1—C8—C9	−143.4 (3)
C6—C1—C2—C3	1.4 (4)	C13—C8—C9—C10	−1.9 (4)
O2—C2—C3—C4	179.0 (3)	N1—C8—C9—C10	−178.1 (2)
C1—C2—C3—C4	−0.7 (4)	C8—C9—C10—C11	1.0 (4)
C2—C3—C4—C5	−0.6 (4)	C8—C9—C10—Cl1	179.0 (2)
C3—C4—C5—C6	1.3 (5)	C9—C10—C11—C12	0.5 (4)
C4—C5—C6—C1	−0.7 (4)	Cl1—C10—C11—C12	−177.5 (2)
C4—C5—C6—C7	−177.7 (3)	C9—C10—C11—Cl2	178.5 (2)
O1—C1—C6—C5	179.9 (3)	Cl1—C10—C11—Cl2	0.5 (4)
C2—C1—C6—C5	−0.7 (4)	C10—C11—C12—C13	−1.1 (4)
O1—C1—C6—C7	−3.1 (4)	Cl2—C11—C12—C13	−179.1 (2)
C2—C1—C6—C7	176.3 (3)	C9—C8—C13—C12	1.3 (4)
C8—N1—C7—C6	−172.6 (2)	N1—C8—C13—C12	177.3 (3)
C5—C6—C7—N1	179.5 (3)	C11—C12—C13—C8	0.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.89	2.608 (3)	146
O2—H2···O1	0.82	2.28	2.729 (3)	115
O2—H2···O1i	0.82	2.20	2.846 (3)	136
C12—H12···Cg1ii	0.93	2.83	3.538 (4)	134

Table 1

Hydrogen-bond geometry (, )

Cg1 is the centroid of the benzene ring (C1C6).

DHA	DH	HA	D A	DHA
O1H1N1	0.82	1.89	2.608(3)	146
O2H2O1	0.82	2.28	2.729(3)	115
O2H2O1i	0.82	2.20	2.846(3)	136
C12H12Cg1ii	0.93	2.83	3.538(4)	134

Symmetry codes: (i) ; (ii) .