3-Chloro-4-(4-chloro-phen-oxy)-N-[(Z)-(5-nitro-thio-phen-2-yl)methyl-idene]aniline.

In the title compound, C(17)H(10)Cl(2)N(2)O(3)S, the thio-phene ring and the central benzene ring are almost coplanar [dihedral angle = 8.44 (3)°], while the dihedral angle between the two benzene rings rings is 77.49 (9)°. The crystal packing is stabilized by inter-molecular C-H⋯O hydrogen bonds.

Related literature

For background to the properties and uses of Schiff bases, see: Barton & Ollis (1979 ▶); Layer (1963 ▶); Ingold (1969 ▶); Cohen et al. (1964 ▶). For comparative bond lengths, see: Özdemir Tarı et al. (2011 ▶); Kazak et al. (2000 ▶); Aygün et al. (1998 ▶).

Experimental

Crystal data

C17H10Cl2N2O3S

M = 393.23

Monoclinic,

a = 16.3698 (9) Å

b = 6.7787 (2) Å

c = 15.9609 (9) Å

β = 105.284 (4)°

V = 1708.47 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.52 mm−1

T = 293 K

0.45 × 0.30 × 0.05 mm

Data collection

Stoe IPDS II diffractometer

Absorption correction: integration (X-RED32; Stoe, 2002) ▶ T min = 0.817, T max = 0.942

10905 measured reflections

3343 independent reflections

2317 reflections with I > 2σ(I)

R int = 0.062

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.124

S = 1.01

3343 reflections

226 parameters

H-atom parameters constrained

Δρmax = 0.73 e Å−3

Δρmin = −0.26 e Å−3

Data collection: X-AREA (Stoe, 2002) ▶; cell refinement: X-AREA ▶; data reduction: X-RED32 (Stoe, 2002) ▶; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶), ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812001316/bt5785sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812001316/bt5785Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812001316/bt5785Isup3.cml

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

C17H10Cl2N2O3S	F(000) = 800
Mr = 393.23	Dx = 1.529 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 14032 reflections
a = 16.3698 (9) Å	θ = 1.3–28.4°
b = 6.7787 (2) Å	µ = 0.52 mm−1
c = 15.9609 (9) Å	T = 293 K
β = 105.284 (4)°	PRISM, brown
V = 1708.47 (14) Å3	0.45 × 0.30 × 0.05 mm
Z = 4

Stoe IPDS II diffractometer	3343 independent reflections
Radiation source: fine-focus sealed tube	2317 reflections with I > 2σ(I)
graphite	Rint = 0.062
Detector resolution: 6.67 pixels mm-1	θmax = 26.0°, θmin = 2.6°
φ scan rotation method	h = −20→20
Absorption correction: integration (X-RED32; Stoe, 2002)	k = −7→8
Tmin = 0.817, Tmax = 0.942	l = −19→16
10905 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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0716P)2] where P = (Fo2 + 2Fc2)/3
3343 reflections	(Δ/σ)max = 0.001
226 parameters	Δρmax = 0.73 e Å−3
0 restraints	Δρmin = −0.26 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
C1	0.58285 (16)	−0.1486 (5)	0.16411 (18)	0.0613 (8)
C2	0.63253 (18)	−0.2004 (5)	0.2450 (2)	0.0652 (8)
H2	0.6545	−0.3273	0.2557	0.078*
C3	0.64914 (17)	−0.0589 (5)	0.31044 (18)	0.0605 (8)
H3	0.6824	−0.0910	0.3655	0.073*
C4	0.61642 (14)	0.1292 (4)	0.29387 (16)	0.0498 (6)
C5	0.56516 (16)	0.1787 (5)	0.21356 (17)	0.0566 (7)
H5	0.5422	0.3047	0.2032	0.068*
C6	0.54833 (17)	0.0374 (5)	0.14815 (18)	0.0622 (8)
H6	0.5137	0.0684	0.0935	0.075*
C7	0.69762 (15)	0.2549 (4)	0.42938 (16)	0.0468 (6)
C8	0.68181 (17)	0.2350 (5)	0.50843 (18)	0.0573 (7)
H8	0.6262	0.2267	0.5122	0.069*
C9	0.74793 (17)	0.2271 (5)	0.58380 (17)	0.0553 (7)
H9	0.7362	0.2155	0.6375	0.066*
C10	0.83122 (15)	0.2364 (4)	0.57930 (15)	0.0439 (6)
C11	0.84728 (16)	0.2591 (4)	0.49868 (16)	0.0484 (6)
H11	0.9028	0.2672	0.4946	0.058*
C12	0.78090 (15)	0.2698 (4)	0.42436 (16)	0.0493 (6)
C13	0.97201 (16)	0.2199 (4)	0.66068 (16)	0.0497 (6)
H13	0.9866	0.2123	0.6083	0.060*
C14	1.03864 (15)	0.2203 (4)	0.74123 (16)	0.0468 (6)
C15	1.12379 (17)	0.2157 (5)	0.74914 (18)	0.0576 (7)
H15	1.1471	0.2089	0.7020	0.069*
C16	1.17241 (17)	0.2224 (4)	0.83561 (18)	0.0553 (7)
H16	1.2313	0.2217	0.8532	0.066*
C17	1.12169 (16)	0.2299 (4)	0.88979 (17)	0.0471 (6)
N1	1.14919 (17)	0.2405 (4)	0.98236 (16)	0.0612 (6)
N2	0.89429 (13)	0.2296 (3)	0.65958 (13)	0.0461 (5)
O1	1.0953 (2)	0.2498 (4)	1.02221 (16)	0.0970 (9)
O2	1.22480 (16)	0.2380 (4)	1.01700 (15)	0.0842 (8)
O3	0.63071 (11)	0.2755 (3)	0.35573 (12)	0.0565 (5)
S1	1.01578 (4)	0.22986 (10)	0.83989 (4)	0.0476 (2)
Cl1	0.56369 (6)	−0.32087 (18)	0.08067 (6)	0.0923 (3)
Cl2	0.80216 (5)	0.30835 (18)	0.32540 (4)	0.0828 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0445 (14)	0.081 (2)	0.0543 (16)	−0.0028 (14)	0.0062 (12)	−0.0082 (16)
C2	0.0536 (16)	0.071 (2)	0.0631 (18)	0.0057 (14)	0.0019 (13)	−0.0003 (16)
C3	0.0503 (15)	0.072 (2)	0.0481 (15)	0.0038 (13)	−0.0069 (12)	0.0053 (14)
C4	0.0382 (12)	0.0660 (18)	0.0418 (13)	−0.0006 (12)	0.0046 (10)	0.0002 (13)
C5	0.0464 (14)	0.072 (2)	0.0451 (14)	0.0038 (13)	0.0017 (11)	0.0075 (14)
C6	0.0513 (15)	0.084 (2)	0.0438 (14)	0.0023 (14)	0.0001 (11)	0.0061 (15)
C7	0.0418 (12)	0.0553 (17)	0.0380 (12)	0.0032 (11)	0.0009 (10)	0.0002 (11)
C8	0.0408 (13)	0.082 (2)	0.0475 (15)	−0.0002 (12)	0.0088 (11)	−0.0007 (14)
C9	0.0497 (14)	0.079 (2)	0.0362 (13)	−0.0028 (13)	0.0088 (11)	0.0001 (13)
C10	0.0464 (13)	0.0454 (15)	0.0352 (12)	−0.0013 (10)	0.0025 (10)	−0.0007 (10)
C11	0.0405 (12)	0.0636 (18)	0.0378 (13)	−0.0019 (11)	0.0045 (10)	−0.0012 (12)
C12	0.0454 (13)	0.0637 (18)	0.0360 (12)	0.0001 (11)	0.0057 (10)	0.0005 (12)
C13	0.0521 (15)	0.0562 (16)	0.0359 (12)	−0.0013 (11)	0.0029 (11)	−0.0003 (11)
C14	0.0468 (13)	0.0489 (15)	0.0397 (12)	−0.0028 (11)	0.0027 (10)	0.0019 (11)
C15	0.0486 (14)	0.077 (2)	0.0458 (14)	−0.0048 (13)	0.0092 (11)	0.0037 (14)
C16	0.0419 (13)	0.0652 (19)	0.0530 (15)	−0.0026 (12)	0.0020 (11)	0.0035 (13)
C17	0.0466 (13)	0.0444 (15)	0.0427 (13)	−0.0035 (10)	−0.0014 (11)	0.0010 (11)
N1	0.0716 (16)	0.0571 (16)	0.0431 (12)	−0.0040 (12)	−0.0055 (12)	−0.0017 (11)
N2	0.0469 (11)	0.0520 (13)	0.0326 (10)	−0.0034 (9)	−0.0013 (8)	−0.0006 (9)
O1	0.106 (2)	0.138 (3)	0.0482 (12)	0.0076 (16)	0.0216 (13)	−0.0073 (14)
O2	0.0833 (16)	0.0886 (18)	0.0569 (13)	−0.0110 (12)	−0.0239 (11)	−0.0014 (11)
O3	0.0443 (9)	0.0723 (14)	0.0440 (10)	0.0095 (8)	−0.0039 (7)	−0.0035 (9)
S1	0.0430 (3)	0.0539 (4)	0.0422 (3)	−0.0016 (3)	0.0049 (2)	−0.0008 (3)
Cl1	0.0864 (6)	0.1102 (8)	0.0710 (6)	0.0071 (5)	0.0042 (4)	−0.0307 (5)
Cl2	0.0535 (4)	0.1552 (9)	0.0373 (4)	−0.0077 (4)	0.0079 (3)	0.0114 (4)

C1—C6	1.378 (5)	C10—C11	1.388 (4)
C1—C2	1.378 (4)	C10—N2	1.419 (3)
C1—Cl1	1.736 (3)	C11—C12	1.383 (3)
C2—C3	1.391 (4)	C11—H11	0.9300
C2—H2	0.9300	C12—Cl2	1.725 (3)
C3—C4	1.381 (4)	C13—N2	1.269 (3)
C3—H3	0.9300	C13—C14	1.450 (3)
C4—O3	1.375 (3)	C13—H13	0.9300
C4—C5	1.376 (4)	C14—C15	1.366 (4)
C5—C6	1.390 (4)	C14—S1	1.713 (3)
C5—H5	0.9300	C15—C16	1.400 (4)
C6—H6	0.9300	C15—H15	0.9300
C7—C8	1.360 (4)	C16—C17	1.348 (4)
C7—O3	1.387 (3)	C16—H16	0.9300
C7—C12	1.390 (4)	C17—N1	1.428 (3)
C8—C9	1.391 (4)	C17—S1	1.707 (2)
C8—H8	0.9300	N1—O2	1.215 (3)
C9—C10	1.386 (4)	N1—O1	1.218 (4)
C9—H9	0.9300
C6—C1—C2	121.2 (3)	C11—C10—N2	124.8 (2)
C6—C1—Cl1	119.4 (2)	C12—C11—C10	120.2 (2)
C2—C1—Cl1	119.3 (3)	C12—C11—H11	119.9
C1—C2—C3	118.5 (3)	C10—C11—H11	119.9
C1—C2—H2	120.7	C11—C12—C7	120.5 (2)
C3—C2—H2	120.7	C11—C12—Cl2	119.4 (2)
C4—C3—C2	120.3 (3)	C7—C12—Cl2	120.10 (19)
C4—C3—H3	119.9	N2—C13—C14	121.9 (3)
C2—C3—H3	119.9	N2—C13—H13	119.0
O3—C4—C5	116.1 (3)	C14—C13—H13	119.0
O3—C4—C3	123.0 (2)	C15—C14—C13	126.3 (3)
C5—C4—C3	121.0 (3)	C15—C14—S1	112.38 (19)
C4—C5—C6	118.9 (3)	C13—C14—S1	121.3 (2)
C4—C5—H5	120.6	C14—C15—C16	113.0 (3)
C6—C5—H5	120.6	C14—C15—H15	123.5
C1—C6—C5	120.1 (3)	C16—C15—H15	123.5
C1—C6—H6	119.9	C17—C16—C15	110.3 (2)
C5—C6—H6	119.9	C17—C16—H16	124.8
C8—C7—O3	119.7 (2)	C15—C16—H16	124.8
C8—C7—C12	119.3 (2)	C16—C17—N1	125.9 (2)
O3—C7—C12	120.7 (2)	C16—C17—S1	115.0 (2)
C7—C8—C9	120.7 (2)	N1—C17—S1	119.1 (2)
C7—C8—H8	119.6	O2—N1—O1	123.7 (3)
C9—C8—H8	119.6	O2—N1—C17	118.4 (3)
C10—C9—C8	120.4 (2)	O1—N1—C17	118.0 (3)
C10—C9—H9	119.8	C13—N2—C10	120.2 (2)
C8—C9—H9	119.8	C4—O3—C7	118.9 (2)
C9—C10—C11	118.9 (2)	C17—S1—C14	89.30 (12)
C9—C10—N2	116.3 (2)
C6—C1—C2—C3	−1.6 (5)	N2—C13—C14—C15	−178.1 (3)
Cl1—C1—C2—C3	178.2 (2)	N2—C13—C14—S1	1.1 (4)
C1—C2—C3—C4	−0.1 (5)	C13—C14—C15—C16	178.5 (3)
C2—C3—C4—O3	−179.9 (3)	S1—C14—C15—C16	−0.7 (3)
C2—C3—C4—C5	1.8 (4)	C14—C15—C16—C17	0.6 (4)
O3—C4—C5—C6	179.9 (2)	C15—C16—C17—N1	−179.2 (3)
C3—C4—C5—C6	−1.6 (4)	C15—C16—C17—S1	−0.1 (3)
C2—C1—C6—C5	1.8 (5)	C16—C17—N1—O2	−1.9 (4)
Cl1—C1—C6—C5	−178.1 (2)	S1—C17—N1—O2	179.1 (2)
C4—C5—C6—C1	−0.1 (4)	C16—C17—N1—O1	178.8 (3)
O3—C7—C8—C9	−175.8 (3)	S1—C17—N1—O1	−0.2 (4)
C12—C7—C8—C9	−0.8 (4)	C14—C13—N2—C10	177.6 (2)
C7—C8—C9—C10	−0.9 (5)	C9—C10—N2—C13	173.8 (2)
C8—C9—C10—C11	1.7 (4)	C11—C10—N2—C13	−8.8 (4)
C8—C9—C10—N2	179.3 (3)	C5—C4—O3—C7	−163.4 (2)
C9—C10—C11—C12	−0.7 (4)	C3—C4—O3—C7	18.2 (4)
N2—C10—C11—C12	−178.1 (3)	C8—C7—O3—C4	−114.7 (3)
C10—C11—C12—C7	−1.0 (4)	C12—C7—O3—C4	70.5 (3)
C10—C11—C12—Cl2	177.3 (2)	C16—C17—S1—C14	−0.2 (2)
C8—C7—C12—C11	1.8 (4)	N1—C17—S1—C14	178.9 (2)
O3—C7—C12—C11	176.7 (2)	C15—C14—S1—C17	0.5 (2)
C8—C7—C12—Cl2	−176.5 (2)	C13—C14—S1—C17	−178.8 (2)
O3—C7—C12—Cl2	−1.6 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2i	0.93	2.38	3.278 (3)	162.
C13—H13···O1ii	0.93	2.53	3.369 (4)	150.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O2i	0.93	2.38	3.278 (3)	162
C13—H13⋯O1ii	0.93	2.53	3.369 (4)	150

Symmetry codes: (i) ; (ii) .