(E)-2-[(2,4-Dichloro-phen-yl)imino-meth-yl]benzene-1,4-diol monohydrate.

The title compound, C(13)H(9)Cl(2)NO(2)·H(2)O, represents a Schiff base which adopts the phenol-imine tautomeric form in the solid state. The mol-ecule is approximately planar (r.m.s. deviation 0.0818 Å), and the dihedral angle between the two aromatic rings is 7.46 (12)°. An O-H⋯N inter-action generates an S(6) ring. In the crystal, mol-ecules are linked by inter-molecular O-H⋯O hydrogen bonds involving the solvent water mol-ecule, forming chains.

Related literature

For the biological properties of Schiff bases see: Lozier et al. (1975 ▶), Dao et al. (2000 ▶). For the coordination chemistry of Schiff bases see: Kargar et al. (2009 ▶); Yeap et al. (2009 ▶). For a discussion of Schiff bases tautomerism, see: Şahin et al. (2005 ▶); Hadjoudis et al. (1987 ▶). For a related structure, see: Zhang (2009 ▶).

Experimental

Crystal data

C13H9Cl2NO2·H2O

M = 300.13

Monoclinic,

a = 4.6899 (2) Å

b = 17.4289 (6) Å

c = 16.1645 (7) Å

β = 95.923 (3)°

V = 1314.23 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.50 mm−1

T = 296 K

0.90 × 0.56 × 0.25 mm

Data collection

Stoe IPDS II diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.801, T max = 0.959

11982 measured reflections

2585 independent reflections

1879 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.098

S = 0.97

2585 reflections

188 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.14 e Å−3

Δρmin = −0.29 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809045103/bh2254sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809045103/bh2254Isup2.hkl

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

C13H9Cl2NO2·H2O	F(000) = 616
Mr = 300.13	Dx = 1.517 Mg m−3
Monoclinic, P21/c	Melting point: 432 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71069 Å
a = 4.6899 (2) Å	Cell parameters from 12355 reflections
b = 17.4289 (6) Å	θ = 1.3–27.2°
c = 16.1645 (7) Å	µ = 0.50 mm−1
β = 95.923 (3)°	T = 296 K
V = 1314.23 (9) Å3	Prism, brown
Z = 4	0.90 × 0.56 × 0.25 mm

Stoe IPDS II diffractometer	2585 independent reflections
Radiation source: fine-focus sealed tube	1879 reflections with I > 2σ(I)
graphite	Rint = 0.050
Detector resolution: 6.67 pixels mm-1	θmax = 26.0°, θmin = 1.7°
ω scans	h = −5→5
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −21→21
Tmin = 0.801, Tmax = 0.959	l = −19→19
11982 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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	w = 1/[σ2(Fo2) + (0.0595P)2] where P = (Fo2 + 2Fc2)/3
2585 reflections	(Δ/σ)max = 0.001
188 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

	x	y	z	Uiso*/Ueq
C1	−0.2010 (4)	0.11322 (10)	0.62421 (11)	0.0455 (4)
C2	−0.3504 (4)	0.09465 (12)	0.54787 (12)	0.0540 (5)
H2A	−0.3024	0.0502	0.5207	0.065*
C3	−0.5665 (4)	0.14033 (12)	0.51181 (12)	0.0556 (5)
C4	−0.6388 (4)	0.20661 (11)	0.55258 (13)	0.0554 (5)
H4	−0.7851	0.2380	0.5287	0.066*
C5	−0.4951 (5)	0.22589 (11)	0.62805 (13)	0.0573 (5)
H5	−0.5461	0.2702	0.6550	0.069*
C6	−0.2748 (4)	0.18020 (11)	0.66461 (12)	0.0510 (4)
C7	0.0230 (4)	0.06279 (11)	0.66080 (12)	0.0485 (4)
H7	0.0640	0.0180	0.6331	0.058*
C8	0.3792 (4)	0.03047 (10)	0.76835 (11)	0.0467 (4)
C9	0.4933 (4)	0.04822 (11)	0.84932 (12)	0.0512 (4)
C10	0.7030 (4)	0.00366 (12)	0.89192 (13)	0.0560 (5)
H11	0.7748	0.0162	0.9460	0.067*
C11	0.8040 (4)	−0.05934 (11)	0.85325 (12)	0.0518 (5)
C12	0.7014 (4)	−0.07811 (11)	0.77313 (12)	0.0547 (5)
H12	0.7737	−0.1205	0.7473	0.066*
C13	0.4907 (4)	−0.03366 (11)	0.73152 (12)	0.0522 (5)
H13	0.4209	−0.0467	0.6774	0.063*
N1	0.1649 (3)	0.07852 (9)	0.73022 (9)	0.0492 (4)
O1	−0.6995 (5)	0.11940 (12)	0.43607 (10)	0.0909 (6)
H1	−0.848 (8)	0.148 (2)	0.420 (2)	0.121 (12)*
O2	−0.1365 (4)	0.20076 (10)	0.73902 (10)	0.0729 (5)
H2	−0.007 (7)	0.166 (2)	0.751 (2)	0.105 (10)*
O3	−1.1524 (5)	0.19928 (14)	0.37204 (14)	0.0930 (7)
H1O	−1.167 (7)	0.232 (2)	0.333 (2)	0.112 (11)*
H2O	−1.317 (10)	0.200 (3)	0.385 (3)	0.154 (17)*
Cl1	1.06563 (11)	−0.11630 (3)	0.90637 (4)	0.06643 (18)
Cl2	0.36487 (14)	0.12696 (4)	0.89962 (4)	0.0773 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0467 (10)	0.0449 (9)	0.0457 (10)	−0.0009 (8)	0.0091 (8)	0.0010 (7)
C2	0.0598 (12)	0.0552 (10)	0.0472 (10)	0.0099 (9)	0.0062 (9)	−0.0040 (9)
C3	0.0594 (12)	0.0662 (12)	0.0413 (10)	0.0084 (10)	0.0053 (9)	0.0013 (9)
C4	0.0566 (11)	0.0518 (11)	0.0582 (12)	0.0069 (9)	0.0081 (10)	0.0098 (9)
C5	0.0635 (12)	0.0437 (10)	0.0648 (13)	0.0071 (9)	0.0073 (10)	−0.0036 (9)
C6	0.0541 (11)	0.0488 (10)	0.0498 (10)	−0.0028 (9)	0.0045 (9)	−0.0059 (8)
C7	0.0508 (10)	0.0473 (10)	0.0477 (10)	0.0023 (8)	0.0068 (9)	−0.0016 (8)
C8	0.0473 (10)	0.0477 (10)	0.0454 (10)	−0.0023 (8)	0.0065 (8)	0.0031 (8)
C9	0.0502 (10)	0.0521 (10)	0.0508 (11)	−0.0012 (8)	0.0033 (9)	−0.0053 (8)
C10	0.0530 (12)	0.0625 (12)	0.0507 (11)	−0.0034 (9)	−0.0031 (9)	−0.0027 (9)
C11	0.0452 (10)	0.0530 (10)	0.0569 (12)	−0.0043 (8)	0.0030 (9)	0.0063 (8)
C12	0.0592 (12)	0.0493 (10)	0.0565 (12)	0.0044 (9)	0.0107 (10)	0.0009 (9)
C13	0.0607 (11)	0.0525 (11)	0.0432 (10)	0.0021 (9)	0.0046 (9)	−0.0015 (8)
N1	0.0502 (8)	0.0501 (9)	0.0468 (9)	0.0016 (7)	0.0034 (7)	0.0011 (7)
O1	0.0986 (13)	0.1152 (15)	0.0533 (9)	0.0486 (12)	−0.0184 (9)	−0.0210 (9)
O2	0.0780 (11)	0.0689 (10)	0.0678 (10)	0.0162 (9)	−0.0120 (8)	−0.0241 (8)
O3	0.0771 (13)	0.1106 (15)	0.0906 (14)	0.0109 (11)	0.0047 (11)	0.0506 (12)
Cl1	0.0588 (3)	0.0651 (3)	0.0733 (4)	0.0055 (2)	−0.0036 (3)	0.0112 (2)
Cl2	0.0850 (4)	0.0770 (4)	0.0669 (4)	0.0199 (3)	−0.0065 (3)	−0.0257 (3)

C1—C2	1.393 (3)	C8—C9	1.397 (3)
C1—C6	1.398 (3)	C8—N1	1.401 (2)
C1—C7	1.448 (3)	C9—C10	1.380 (3)
C2—C3	1.371 (3)	C9—Cl2	1.734 (2)
C2—H2A	0.9300	C10—C11	1.372 (3)
C3—O1	1.365 (3)	C10—H11	0.9300
C3—C4	1.389 (3)	C11—C12	1.374 (3)
C4—C5	1.373 (3)	C11—Cl1	1.735 (2)
C4—H4	0.9300	C12—C13	1.375 (3)
C5—C6	1.388 (3)	C12—H12	0.9300
C5—H5	0.9300	C13—H13	0.9300
C6—O2	1.354 (2)	O1—H1	0.87 (4)
C7—N1	1.274 (2)	O2—H2	0.87 (4)
C7—H7	0.9300	O3—H1O	0.85 (4)
C8—C13	1.393 (3)	O3—H2O	0.82 (4)
C2—C1—C6	118.80 (17)	C13—C8—N1	125.12 (17)
C2—C1—C7	119.88 (16)	C9—C8—N1	117.89 (16)
C6—C1—C7	121.32 (17)	C10—C9—C8	121.82 (18)
C3—C2—C1	121.61 (18)	C10—C9—Cl2	118.39 (16)
C3—C2—H2A	119.2	C8—C9—Cl2	119.78 (15)
C1—C2—H2A	119.2	C11—C10—C9	119.00 (19)
O1—C3—C2	118.39 (18)	C11—C10—H11	120.5
O1—C3—C4	122.44 (19)	C9—C10—H11	120.5
C2—C3—C4	119.16 (19)	C10—C11—C12	121.10 (19)
C5—C4—C3	120.22 (19)	C10—C11—Cl1	119.48 (16)
C5—C4—H4	119.9	C12—C11—Cl1	119.42 (16)
C3—C4—H4	119.9	C11—C12—C13	119.40 (18)
C4—C5—C6	120.91 (18)	C11—C12—H12	120.3
C4—C5—H5	119.5	C13—C12—H12	120.3
C6—C5—H5	119.5	C12—C13—C8	121.69 (18)
O2—C6—C5	119.58 (18)	C12—C13—H13	119.2
O2—C6—C1	121.12 (18)	C8—C13—H13	119.2
C5—C6—C1	119.30 (18)	C7—N1—C8	122.99 (16)
N1—C7—C1	121.34 (17)	C3—O1—H1	113 (2)
N1—C7—H7	119.3	C6—O2—H2	106 (2)
C1—C7—H7	119.3	H1O—O3—H2O	100 (4)
C13—C8—C9	116.98 (18)
C6—C1—C2—C3	0.0 (3)	N1—C8—C9—C10	179.39 (17)
C7—C1—C2—C3	179.05 (17)	C13—C8—C9—Cl2	−179.77 (14)
C1—C2—C3—O1	178.63 (19)	N1—C8—C9—Cl2	0.9 (2)
C1—C2—C3—C4	−0.2 (3)	C8—C9—C10—C11	0.7 (3)
O1—C3—C4—C5	−178.8 (2)	Cl2—C9—C10—C11	179.20 (15)
C2—C3—C4—C5	0.0 (3)	C9—C10—C11—C12	0.5 (3)
C3—C4—C5—C6	0.5 (3)	C9—C10—C11—Cl1	−179.49 (14)
C4—C5—C6—O2	179.88 (19)	C10—C11—C12—C13	−1.0 (3)
C4—C5—C6—C1	−0.7 (3)	Cl1—C11—C12—C13	178.96 (15)
C2—C1—C6—O2	179.87 (18)	C11—C12—C13—C8	0.4 (3)
C7—C1—C6—O2	0.8 (3)	C9—C8—C13—C12	0.7 (3)
C2—C1—C6—C5	0.5 (3)	N1—C8—C13—C12	−179.98 (17)
C7—C1—C6—C5	−178.58 (18)	C1—C7—N1—C8	178.71 (16)
C2—C1—C7—N1	179.43 (17)	C13—C8—N1—C7	9.2 (3)
C6—C1—C7—N1	−1.5 (3)	C9—C8—N1—C7	−171.48 (17)
C13—C8—C9—C10	−1.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1O···O2i	0.85 (4)	1.94 (4)	2.774 (3)	170 (3)
O2—H2···N1	0.87 (4)	1.77 (3)	2.569 (2)	152 (3)
O3—H2O···O1ii	0.82 (4)	2.49 (5)	3.184 (3)	143 (4)
O1—H1···O3	0.87 (4)	1.79 (4)	2.659 (3)	171 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H1O⋯O2i	0.85 (4)	1.94 (4)	2.774 (3)	170 (3)
O2—H2⋯N1	0.87 (4)	1.77 (3)	2.569 (2)	152 (3)
O3—H2O⋯O1ii	0.82 (4)	2.49 (5)	3.184 (3)	143 (4)
O1—H1⋯O3	0.87 (4)	1.79 (4)	2.659 (3)	171 (3)

Symmetry codes: (i) ; (ii) .