3-Chloro-4-(4-chloro­phen­oxy)-N-[(Z)-(5-nitro­thio­phen-2-yl)methyl­idene]aniline

Özdemir Tarı, G.; Işık, Ş.

doi:10.1107/S1600536812001316

organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o415

doi:10.1107/S1600536812001316

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3-Chloro-4-(4-chlorophenoxy)-N-[(Z)-(5-nitrothiophen-2-yl)methylidene]aniline

Gonca Özdemir Tarı ^a ^* and Şamil Işık ^a

^aDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, Kurupelit, TR-55139 Samsun, Turkey
^*Correspondence e-mail: gozdemir@omu.edu.tr

(Received 9 January 2012; accepted 11 January 2012; online 14 January 2012)

In the title compound, C₁₇H₁₀Cl₂N₂O₃S, the thiophene 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 intermolecular 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_r = 393.23
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.050
wR(F²) = 0.124
S = 1.01
3343 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.73 e Å⁻³
Δρ_min = −0.26 e Å⁻³

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) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812001316/bt5785sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812001316/bt5785Isup3.cml

checkCIF report

Comment top

Schiff bases are used as starting materials in the synthesis of important drugs, such as antibiotics and antiallergic, antiphlogistic, and antitumor substances (Barton et al., 1979; Layer, 1963; Ingold 1969). They show photochromism and thermochromism (Cohen et al., 1964).

In this paper, the structure of the title compound, is reported. The N2=C13 bond length of 1.269 (3)Å is typical of a double bond, which is similar to the corresponding bond length in 2-[(4-Hydroxyphenyl)iminomethyl]-thiophene [1.282 (2) Å; Kazak et al., 2000]; 3-methoxy-2-[(E)-(4-methoxyphenyl)imino)methyl)phenol [1.278 (3) Å, Özdemir Tarı et al., 2011] and N-(2,4-dinitrophenyl)-N-methylhydrozone [1.279 (2) Å, Aygün et al., 1998].

The N2—C10 bond distance is 1.419 (3) Å, which is in good agreement with the corresponding bond lengths in 2-[(4-Hydroxyphenyl)iminomethyl]-thiophene [1.422 (2) Å, Kazak et al., 2000] and 3-methoxy-2-[(E)-(4-methoxyphenyl) imino)methyl)phenol [1.419 (2) Å, Özdemir Tarı et al., 2011].

The C14—S1 and the C17—S1 distance are 1.713 (3)Å and 1.707 (2) Å, respectively. These distances are in good agreement with a related compound [1.712 (2)Å and 1.705 (3) Å; Kazak et al., 2000]. The S···N2 distance is 3.036Å agree with similar length in related compound [3.135 (2) Å; Kazak et al.,2000].

Thermochromism or photochromism depends on the planarity or non-planarity of the molecule, respectively. The title compound might have photochromic properties because of the non-planarity of the molecule. The crystal structure is stabilized by intermolecular C—H···O hydrogen bonds.

Related literature top

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 top

The compound (Z)—N-[3-chloro-4-(4-chlorophenoxy)phenyl]-1-(5-nitrothiophen-2-yl) methanimine was prepared by refluxing a mixture of a solution containing 5-nitro-2-thiophene-carboxaldehyde (0.077 g 0.049 mmol) in 20 ml ethanol and a solution containing 3-Chloro-4-(4-Chloro-phenoxy)aniline (0.012 g 0.049 mmol) in 20 ml ethanol. The reaction mixture was stirred for 1 h under reflux. The crystals of (Z)—N-[3-chloro-4-(4-chlorophenoxy)phenyl]-1-(5-nitrothiophen-2-yl)methanimine suitable for X-ray analysis were obtained from ethylalcohol by slow evaporation (yield % 78; m.p 402–404K).

Computing details top

Data collection: X-AREA (Stoe, 2002); cell refinement: X-AREA (Stoe, 2002); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme and 30% probability diplacement ellipsoids.
	Fig. 2. The crystal packing of the title compound. Intermolecular hydrogen bonds are shown as dashed lines.

3-Chloro-4-(4-chlorophenoxy)-N-[(Z)-(5-nitrothiophen-2- yl)methylidene]aniline top

Crystal data top

C₁₇H₁₀Cl₂N₂O₃S	F(000) = 800
M_r = 393.23	D_x = 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

Data collection top

Stoe IPDS II diffractometer	3343 independent reflections
Radiation source: fine-focus sealed tube	2317 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.062
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.0°, θ_min = 2.6°
ϕ scan rotation method	h = −20→20
Absorption correction: integration (X-RED32; Stoe, 2002)	k = −7→8
T_min = 0.817, T_max = 0.942	l = −19→16
10905 measured reflections

Refinement top

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(F_o²) + (0.0716P)²] where P = (F_o² + 2F_c²)/3
3343 reflections	(Δ/σ)_max = 0.001
226 parameters	Δρ_max = 0.73 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₇H₁₀Cl₂N₂O₃S	V = 1708.47 (14) Å³
M_r = 393.23	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.3698 (9) Å	µ = 0.52 mm⁻¹
b = 6.7787 (2) Å	T = 293 K
c = 15.9609 (9) Å	0.45 × 0.30 × 0.05 mm
β = 105.284 (4)°

Data collection top

Stoe IPDS II diffractometer	3343 independent reflections
Absorption correction: integration (X-RED32; Stoe, 2002)	2317 reflections with I > 2σ(I)
T_min = 0.817, T_max = 0.942	R_int = 0.062
10905 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.124	H-atom parameters constrained
S = 1.01	Δρ_max = 0.73 e Å⁻³
3343 reflections	Δρ_min = −0.26 e Å⁻³
226 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+2, y−1/2, −z+3/2; (ii) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₀Cl₂N₂O₃S
M_r	393.23
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	16.3698 (9), 6.7787 (2), 15.9609 (9)
β (°)	105.284 (4)
V (Å³)	1708.47 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.52
Crystal size (mm)	0.45 × 0.30 × 0.05

Data collection
Diffractometer	Stoe IPDS II diffractometer
Absorption correction	Integration (X-RED32; Stoe, 2002)
T_min, T_max	0.817, 0.942
No. of measured, independent and observed [I > 2σ(I)] reflections	10905, 3343, 2317
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.124, 1.01
No. of reflections	3343
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.73, −0.26

Computer programs: X-AREA (Stoe, 2002), X-RED32 (Stoe, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2ⁱ	0.93	2.38	3.278 (3)	162.2
C13—H13···O1ⁱⁱ	0.93	2.53	3.369 (4)	150.1

Symmetry codes: (i) −x+2, y−1/2, −z+3/2; (ii) x, −y+1/2, z−1/2.

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS II diffractometer (purchased under grant No. F279 of the University Research Fund).

References

Aygün, M., Işik, Ş., Öcal, N., Tahir, M. N., Kaban, Ş. & Büyükgüngör, O. (1998). Acta Cryst. C54, 527–529. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Kazak, C., Aygün, M., Turgut, G., Odabaşoĝlu, M., Özbey, S. & Büyükgüngör, O. (2000). Acta Cryst. C56, 1044–1045. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
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Volume 68| Part 2| February 2012| Page o415

doi:10.1107/S1600536812001316

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

3-Chloro-4-(4-chloro­phen­­oxy)-N-[(Z)-(5-nitro­thio­phen-2-yl)methyl­­idene]aniline

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3-Chloro-4-(4-chlorophenoxy)-N-[(Z)-(5-nitrothiophen-2-yl)methylidene]aniline