2-{[3-Chloro-4-(4-chloro-phen-oxy)phen-yl]imino-meth-yl}-4-nitro-phenol.

In the title compound, C19H12Cl2N2O4, the imine bond length of 1.257 (6) Å is typical of a double bond. The dihedral angle between the para-nitro benzene ring and the central benzene ring is 12.06 (3)° and that between the central benzene and the para-chloro benzene ring is 73.81 (2)°. An intra-molecular O-H⋯N hydrogen bond generates an S(6) ring motif. In the crystal, mol-ecules are linked together by two pairs of C-H⋯O interactions (to the same O atom acceptor), forming inversion dimers. A short Cl⋯Cl contact [3.232 (4) Å] is observed.

Related literature

For applications of related Schiff base compounds, see: Santos et al. (2001 ▶); Cohen et al. (1964 ▶). For related structures, see: Aygün et al. (1998 ▶); Karadayı et al. (2003 ▶, 2005 ▶, 2006 ▶); Faridbod et al. (2008 ▶); Raja et al. (2008 ▶); Li & Zhang (2004 ▶); Köysal et al. (2012 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C19H12Cl2N2O4

M = 403.21

Triclinic,

a = 5.5649 (8) Å

b = 7.929 (1) Å

c = 21.778 (4) Å

α = 86.260 (12)°

β = 83.596 (12)°

γ = 70.739 (10)°

V = 901.1 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.39 mm−1

T = 296 K

0.76 × 0.39 × 0.03 mm

Data collection

Stoe IPDS 2 diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.849, T max = 0.985

10061 measured reflections

3475 independent reflections

1473 reflections with I > 2σ(I)

R int = 0.076

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.186

S = 1.05

3475 reflections

248 parameters

52 restraints

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.22 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); 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, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813012518/rn2114sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813012518/rn2114Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813012518/rn2114Isup3.cml

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

C19H12Cl2N2O4	Z = 2
Mr = 403.21	F(000) = 412
Triclinic, P1	Dx = 1.486 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.5649 (8) Å	Cell parameters from 8340 reflections
b = 7.929 (1) Å	θ = 1.9–28.2°
c = 21.778 (4) Å	µ = 0.39 mm−1
α = 86.260 (12)°	T = 296 K
β = 83.596 (12)°	Plate, yellow
γ = 70.739 (10)°	0.76 × 0.39 × 0.03 mm
V = 901.1 (2) Å3

Stoe IPDS 2 diffractometer	3475 independent reflections
Radiation source: fine-focus sealed tube	1473 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.076
ω scans	θmax = 26.0°, θmin = 1.9°
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	h = −6→6
Tmin = 0.849, Tmax = 0.985	k = −9→9
10061 measured reflections	l = −26→26

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.068	H-atom parameters constrained
wR(F2) = 0.186	w = 1/[σ2(Fo2) + (0.0634P)2 + 0.1371P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
3475 reflections	Δρmax = 0.20 e Å−3
248 parameters	Δρmin = −0.22 e Å−3
52 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.011 (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
Cl2	0.7962 (6)	−0.3765 (3)	0.45465 (11)	0.2198 (11)
Cl1	−0.0539 (2)	0.30360 (16)	0.22683 (8)	0.1373 (6)
C18	0.6896 (14)	−0.0931 (8)	0.3740 (3)	0.144 (2)
H18	0.8584	−0.1407	0.3573	0.173*
C17	0.6001 (16)	−0.1794 (9)	0.4229 (3)	0.156 (2)
C19	0.5349 (14)	0.0624 (8)	0.3493 (3)	0.142 (2)
H19	0.5998	0.1220	0.3168	0.171*
C16	0.3486 (18)	−0.1156 (11)	0.4467 (3)	0.177 (3)
H16	0.2860	−0.1763	0.4792	0.213*
O3	0.0233 (6)	1.2311 (4)	−0.04140 (18)	0.1345 (13)
C15	0.1920 (16)	0.0391 (11)	0.4217 (3)	0.161 (3)
H15	0.0222	0.0837	0.4379	0.193*
C14	0.2795 (15)	0.1313 (9)	0.3728 (3)	0.135 (2)
O2	0.2457 (6)	1.4083 (4)	−0.05235 (18)	0.1303 (13)
N2	0.1826 (7)	1.2896 (5)	−0.0236 (3)	0.1123 (14)
C10	0.1116 (9)	0.4319 (6)	0.2530 (3)	0.1125 (17)
C6	0.2397 (8)	1.0768 (5)	0.0639 (3)	0.1007 (16)
H6	0.1264	1.0298	0.0487	0.121*
C9	0.1661 (8)	0.5615 (5)	0.2153 (3)	0.1149 (17)
H9	0.1109	0.5833	0.1759	0.138*
C5	0.2973 (8)	1.2175 (5)	0.0331 (3)	0.1021 (16)
O4	0.1060 (9)	0.2799 (7)	0.3499 (2)	0.1582 (18)
C11	0.1866 (11)	0.3996 (7)	0.3121 (3)	0.129 (2)
C4	0.4639 (9)	1.2908 (6)	0.0547 (3)	0.1136 (18)
H4	0.5006	1.3863	0.0335	0.136*
C1	0.3481 (8)	1.0065 (5)	0.1168 (3)	0.0988 (15)
C7	0.2800 (9)	0.8626 (6)	0.1508 (3)	0.1049 (16)
H7	0.1647	0.8174	0.1355	0.126*
C8	0.3057 (8)	0.6620 (6)	0.2360 (3)	0.1062 (15)
C2	0.5222 (9)	1.0794 (6)	0.1393 (3)	0.1050 (15)
N1	0.3733 (7)	0.7978 (5)	0.2004 (2)	0.1090 (13)
C3	0.5729 (9)	1.2220 (7)	0.1071 (3)	0.1227 (19)
H3	0.6844	1.2715	0.1219	0.147*
O1	0.6321 (7)	1.0140 (5)	0.1906 (2)	0.1368 (13)
H1	0.6007	0.9221	0.2019	0.205*
C13	0.3831 (11)	0.6245 (7)	0.2947 (3)	0.1260 (18)
H13	0.4780	0.6887	0.3087	0.151*
C12	0.3265 (11)	0.4975 (8)	0.3331 (3)	0.147 (2)
H12	0.3801	0.4765	0.3727	0.177*

	U11	U22	U33	U12	U13	U23
Cl2	0.339 (3)	0.1660 (17)	0.1594 (17)	−0.100 (2)	−0.0038 (18)	0.0157 (15)
Cl1	0.1270 (10)	0.1025 (8)	0.1993 (15)	−0.0557 (7)	−0.0076 (9)	−0.0410 (9)
C18	0.203 (6)	0.128 (4)	0.126 (5)	−0.095 (4)	0.022 (4)	−0.023 (4)
C17	0.258 (7)	0.142 (5)	0.100 (4)	−0.112 (5)	0.006 (5)	−0.019 (3)
C19	0.190 (6)	0.125 (4)	0.140 (5)	−0.098 (4)	0.020 (4)	−0.021 (4)
C16	0.273 (9)	0.182 (6)	0.103 (5)	−0.124 (6)	0.038 (5)	−0.013 (4)
O3	0.137 (2)	0.103 (2)	0.195 (4)	−0.068 (2)	−0.055 (2)	−0.010 (2)
C15	0.229 (7)	0.175 (5)	0.106 (5)	−0.113 (5)	0.033 (5)	−0.025 (4)
C14	0.196 (6)	0.123 (4)	0.120 (4)	−0.100 (4)	0.019 (5)	−0.037 (4)
O2	0.134 (3)	0.0930 (19)	0.184 (4)	−0.0598 (19)	−0.028 (2)	−0.004 (2)
N2	0.098 (3)	0.071 (2)	0.178 (4)	−0.037 (2)	−0.009 (3)	−0.032 (3)
C10	0.104 (3)	0.080 (3)	0.157 (5)	−0.032 (2)	0.000 (3)	−0.037 (3)
C6	0.081 (3)	0.069 (2)	0.160 (5)	−0.030 (2)	−0.014 (3)	−0.024 (3)
C9	0.106 (3)	0.080 (2)	0.164 (5)	−0.031 (2)	−0.016 (3)	−0.033 (3)
C5	0.081 (3)	0.070 (2)	0.161 (5)	−0.027 (2)	−0.008 (3)	−0.028 (3)
O4	0.169 (4)	0.153 (3)	0.178 (4)	−0.095 (3)	0.025 (3)	−0.029 (4)
C11	0.139 (4)	0.110 (4)	0.154 (5)	−0.065 (3)	0.017 (4)	−0.034 (4)
C4	0.095 (3)	0.086 (3)	0.177 (5)	−0.048 (3)	−0.018 (3)	−0.023 (3)
C1	0.079 (3)	0.066 (2)	0.157 (5)	−0.026 (2)	−0.013 (3)	−0.023 (3)
C7	0.090 (3)	0.077 (3)	0.153 (5)	−0.027 (2)	−0.017 (3)	−0.024 (3)
C8	0.104 (3)	0.079 (3)	0.139 (5)	−0.032 (2)	−0.009 (3)	−0.022 (3)
C2	0.085 (3)	0.086 (3)	0.151 (5)	−0.031 (2)	−0.027 (3)	−0.013 (3)
N1	0.103 (3)	0.080 (2)	0.153 (4)	−0.037 (2)	−0.015 (3)	−0.021 (3)
C3	0.098 (3)	0.106 (3)	0.186 (6)	−0.057 (3)	−0.024 (4)	−0.018 (4)
O1	0.120 (3)	0.124 (3)	0.191 (4)	−0.063 (2)	−0.045 (3)	−0.004 (3)
C13	0.145 (4)	0.111 (4)	0.143 (5)	−0.066 (3)	−0.016 (4)	−0.019 (4)
C12	0.189 (6)	0.141 (4)	0.143 (5)	−0.094 (5)	−0.009 (4)	−0.023 (4)

Cl2—C17	1.735 (8)	C9—C8	1.405 (6)
Cl1—C10	1.737 (4)	C9—H9	0.9300
C18—C17	1.365 (8)	C5—C4	1.381 (6)
C18—C19	1.367 (8)	O4—C11	1.370 (7)
C18—H18	0.9300	C11—C12	1.394 (7)
C17—C16	1.374 (9)	C4—C3	1.350 (7)
C19—C14	1.394 (8)	C4—H4	0.9300
C19—H19	0.9300	C1—C2	1.424 (6)
C16—C15	1.370 (10)	C1—C7	1.452 (7)
C16—H16	0.9300	C7—N1	1.257 (6)
O3—N2	1.234 (4)	C7—H7	0.9300
C15—C14	1.386 (8)	C8—C13	1.377 (7)
C15—H15	0.9300	C8—N1	1.412 (6)
C14—O4	1.360 (8)	C2—O1	1.326 (6)
O2—N2	1.222 (5)	C2—C3	1.383 (7)
N2—C5	1.449 (6)	C3—H3	0.9300
C10—C9	1.365 (7)	O1—H1	0.8200
C10—C11	1.379 (8)	C13—C12	1.361 (7)
C6—C1	1.360 (6)	C13—H13	0.9300
C6—C5	1.375 (6)	C12—H12	0.9300
C6—H6	0.9300
C17—C18—C19	121.0 (7)	C4—C5—N2	119.3 (5)
C17—C18—H18	119.5	C14—O4—C11	120.2 (5)
C19—C18—H18	119.5	O4—C11—C10	118.5 (5)
C18—C17—C16	120.5 (8)	O4—C11—C12	121.8 (7)
C18—C17—Cl2	121.1 (7)	C10—C11—C12	119.5 (6)
C16—C17—Cl2	118.3 (6)	C3—C4—C5	119.2 (5)
C18—C19—C14	119.8 (6)	C3—C4—H4	120.4
C18—C19—H19	120.1	C5—C4—H4	120.4
C14—C19—H19	120.1	C6—C1—C2	119.3 (5)
C15—C16—C17	118.7 (7)	C6—C1—C7	120.2 (4)
C15—C16—H16	120.6	C2—C1—C7	120.5 (6)
C17—C16—H16	120.6	N1—C7—C1	121.4 (5)
C16—C15—C14	121.9 (8)	N1—C7—H7	119.3
C16—C15—H15	119.1	C1—C7—H7	119.3
C14—C15—H15	119.1	C13—C8—C9	117.8 (5)
O4—C14—C15	117.2 (7)	C13—C8—N1	117.9 (5)
O4—C14—C19	124.7 (6)	C9—C8—N1	124.3 (6)
C15—C14—C19	118.1 (8)	O1—C2—C3	120.2 (5)
O2—N2—O3	121.7 (5)	O1—C2—C1	121.0 (5)
O2—N2—C5	118.7 (4)	C3—C2—C1	118.7 (6)
O3—N2—C5	119.6 (4)	C7—N1—C8	123.2 (5)
C9—C10—C11	121.1 (5)	C4—C3—C2	121.4 (5)
C9—C10—Cl1	120.1 (5)	C4—C3—H3	119.3
C11—C10—Cl1	118.8 (5)	C2—C3—H3	119.3
C1—C6—C5	120.0 (4)	C2—O1—H1	109.5
C1—C6—H6	120.0	C12—C13—C8	122.8 (5)
C5—C6—H6	120.0	C12—C13—H13	118.6
C10—C9—C8	120.0 (6)	C8—C13—H13	118.6
C10—C9—H9	120.0	C13—C12—C11	118.8 (6)
C8—C9—H9	120.0	C13—C12—H12	120.6
C6—C5—C4	121.3 (6)	C11—C12—H12	120.6
C6—C5—N2	119.3 (4)
C14—C15—C16—C17	0.8 (11)	C16—C17—C18—C19	2.7 (9)
C15—C16—C17—C18	−2.0 (10)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.85	2.564 (5)	145
C7—H7···O3i	0.93	2.51	3.321 (6)	146
C6—H6···O3i	0.93	2.49	3.319 (4)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.85	2.564 (5)	145
C7—H7⋯O3i	0.93	2.51	3.321 (6)	146
C6—H6⋯O3i	0.93	2.49	3.319 (4)	148

Symmetry code: (i) .