(Z)-6-[(5-Chloro-2-hydroxy­phenyl)­aminomethyl­ene]-2-ethoxy­cyclo­hexa-2,4-dienone

Özek, A.; Albayrak, Ç.; Büyükgüngör, O.

doi:10.1107/S1600536809031298

organic compounds

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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page o2153

doi:10.1107/S1600536809031298

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(Z)-6-[(5-Chloro-2-hydroxyphenyl)aminomethylene]-2-ethoxycyclohexa-2,4-dienone

Arzu Özek,^a ^* Çiğdem Albayrak ^b and Orhan Büyükgüngör ^a

^aDepartment of Physics, Ondokuz Mayıs University, TR-55139, Samsun, Turkey, and ^bFaculty of Education, Sinop University, Sinop, Turkey
^*Correspondence e-mail: arzuozek@omu.edu.tr

(Received 4 August 2009; accepted 7 August 2009; online 15 August 2009)

The title compound, C₁₅H₁₄ClNO₃, exists as the keto–amine form in the crystal and two intramolecular N—H⋯O hydrogen bonds are observed. The aromatic rings are oriented at a dihedral angle of 5.85 (8)°. In the crystal structure, intermolecular O—H⋯O and C—H⋯O hydrogen bonds link the molecules into chains. A π–π contact between the benzene rings [centroid–centroid distance = 3.6623 (10) Å] further stabilizes the structure.

Related literature

For general background, see: Büyükgüngör et al. (2007 ); Ersanlı et al. (2003 ); Tanak et al. (2008 ) For related structures, see: Özek et al. (2007 , 2008 ).

Experimental

Crystal data

C₁₅H₁₄ClNO₃
M_r = 291.72
Monoclinic, P 2₁ /c
a = 15.4313 (7) Å
b = 7.1710 (2) Å
c = 12.6071 (6) Å
β = 111.168 (4)°
V = 1300.94 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 296 K
0.52 × 0.29 × 0.09 mm

Data collection

STOE IPDS II diffractometer
Absorption correction: integration X-RED32 (Stoe & Cie, 2002 ) T_min = 0.616, T_max = 0.927
15989 measured reflections
2680 independent reflections
2084 reflections with I > 2σ(I)
R_int = 0.060

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.099
S = 1.05
2680 reflections
237 parameters
All H-atom parameters refined
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.86 (2)	1.88 (2)	2.5957 (17)	140 (2)
N1—H1⋯O3	0.86 (2)	2.29 (2)	2.640 (2)	104.3 (17)
O3—H3⋯O1ⁱ	0.85 (2)	1.79 (2)	2.6258 (17)	165 (2)
C9—H9⋯O3ⁱⁱ	0.96 (2)	2.594 (19)	3.419 (2)	143.8 (14)
Symmetry codes: (i) -x+1, -y, -z+1; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809031298/bt5027sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809031298/bt5027Isup2.hkl

checkCIF report

Comment top

As part of our ongoing studies on the syntheses and structural characterizations of Schiff-base compounds (Özek et al., 2008; Özek et al., 2007), we report here in the crystal structure of the title compound.

Schiff bases display two possible tautomeric forms, namely phenol-imine (O—H···N) and keto-amine (N—H···O) forms. o-Hydroxy Schiff bases have previously been observed in the keto form (Tanak et al., 2008) and in the enol form (Büyükgüngör et al., 2007).

The H atom in title compound (I) is located on atom N1, thus the keto-amine tautomer is favored over the phenol-imine form, as indicated by C2—O1 [1.279 (2) Å], C9—N1 [1.310 (2) Å], C1—C9 [1.410 (2) Å] and C1—C2 [1.432 (2) Å] bonds (Fig. 1). The O1—C2 bond length of 1.279 (2) Å indicates double-bond character, whereas the N1—C9 bond length of 1.310 (2) Å indicates a high degree of single-bond character. Similar results were observed for 2-[(2-Hydroxy- 4-nitrophenyl)-aminomethylene]cyclohexa-3,5-dien-1(2H)-οne [C—O = 1.298 (2) and C—N =1.308 (2) Å; Ersanlı et al., 2003].

It is known that Schiff bases may exhibit thermochromism or photochromism, depending on the planarity or non-planarity of the molecule, respectively. Therefore, one can expect thermochromic properties in the title compound caused by planarity of the molecule; the dihedral angle between rings A (C1—C6) and B (C10—C15) is 5.85 (8)°. Intramolecular N—H···O hydrogen bonds (Table 1) result in the formations of planar six- and five-membered rings C (O1/N1/C1/C2/C9/H1) and D (O3/N1/C10/C11/H1). They are oriented with respect to the adjacent rings at dihedral angles of A/C = 1.65 (9), A/D = 5.12 (9), B/C = 7.29 (7), B/D = 4.51 (5) and C/D = 5.61 (12) °. So, they are nearly coplanar.

In the crystal structure, molecules are linked into a three-dimensional network by intermolecular C—H···O and O—H···O hyrogen bonds (Table 1). The C—H···O hydrogen bonds generate C(6) chains along the c axis and O—H···O hydrogen bonds generate R₂²(18) ring motif (Fig. 2). The π···π contact between the phenyl rings, Cg1—Cg2ⁱ [symmetry code: (i) 1 - x, 1/2 + y, 1/2 - z, where Cg1 and Cg2 are centroids of the rings A (C1—C6) and B (C10—C15), respectively] may further stabilize the structure, with centroid-centroid distance of 3.6623 (10) Å.

Related literature top

For general background, see: Büyükgüngör et al. (2007); Ersanlı et al. (2003); Tanak et al. (2008) For related structures, see: Özek et al. (2007, 2008).

Experimental top

The compound (Z)-6-[(5-chloro-2-hydroxyphenylamino)methylene]-2- ethoxycyclohexa-2,4-dienone was prepared by reflux a mixture of a solution containing 3-ethoxy-2-hydroxybenzaldehyde (0.5 g 3 mmol) in 20 ml e thanol and a solution containing 5-chloro-2-hydroxyaniline (0.43 g 3 mmol) in 20 ml e thanol. The reaction mixture was stirred for 1 h under reflux. The crystals of (Z)-6-[(5-chloro-2-hydroxyphenylamino) methylene]-2-ethoxycyclohexa-2,4-dienone suitable for X-ray analysis were obtained from ethanol by slow evaporation (yield % 89; m.p. 489–491 K).

Computing details top

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, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. A view of (I), with the atom-numbering scheme and 30% probability displacement ellipsoids. Dashed line indicates intramolecular hydrogen bond.
	Fig. 2. A partial packing view of (I), showing the intermolecular C—H···O and O—H···O hydrogen bonds. Dashed lines indicate hydrogen bonds. H atoms are represented as small spheres of arbitrary radii and H atoms not involved in hydrogen bonding have been omitted for clarity. [Symmetry codes: (i): x, -y + 1/2, z + 1/2; (ii): 1 - x, -y, 1 - z].

(Z)-6-[(5-Chloro-2-hydroxyphenyl)aminomethylene]-2-ethoxycyclohexa-2,4- dienone top

Crystal data top

C₁₅H₁₄ClNO₃	F(000) = 608
M_r = 291.72	D_x = 1.489 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 15989 reflections
a = 15.4313 (7) Å	θ = 2.8–26.5°
b = 7.1710 (2) Å	µ = 0.30 mm⁻¹
c = 12.6071 (6) Å	T = 296 K
β = 111.168 (4)°	Prism, red
V = 1300.94 (10) Å³	0.52 × 0.29 × 0.09 mm
Z = 4

Data collection top

STOE IPDS II diffractometer	2680 independent reflections
Radiation source: fine-focus sealed tube	2084 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.060
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.5°, θ_min = 2.8°
ω scans	h = −19→19
Absorption correction: integration X-RED32 (Stoe & Cie, 2002)	k = −8→8
T_min = 0.616, T_max = 0.927	l = −15→15
15989 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.099	All H-atom parameters refined
S = 1.05	w = 1/[σ²(F_o²) + (0.0546P)² + 0.0402P] where P = (F_o² + 2F_c²)/3
2680 reflections	(Δ/σ)_max < 0.001
237 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₅H₁₄ClNO₃	V = 1300.94 (10) Å³
M_r = 291.72	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.4313 (7) Å	µ = 0.30 mm⁻¹
b = 7.1710 (2) Å	T = 296 K
c = 12.6071 (6) Å	0.52 × 0.29 × 0.09 mm
β = 111.168 (4)°

Data collection top

STOE IPDS II diffractometer	2680 independent reflections
Absorption correction: integration X-RED32 (Stoe & Cie, 2002)	2084 reflections with I > 2σ(I)
T_min = 0.616, T_max = 0.927	R_int = 0.060
15989 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.099	All H-atom parameters refined
S = 1.05	Δρ_max = 0.15 e Å⁻³
2680 reflections	Δρ_min = −0.25 e Å⁻³
237 parameters

Special details top

Experimental. 314 frames, detector distance = 100 mm

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	0.42045 (11)	0.1210 (2)	0.12588 (13)	0.0348 (3)
C2	0.35762 (11)	0.0951 (2)	0.18490 (13)	0.0347 (3)
C3	0.25975 (11)	0.0968 (2)	0.11617 (14)	0.0354 (4)
C4	0.23136 (12)	0.1153 (2)	0.00038 (14)	0.0405 (4)
C5	0.29497 (13)	0.1391 (3)	−0.05529 (15)	0.0420 (4)
C6	0.38735 (12)	0.1431 (2)	0.00582 (14)	0.0397 (4)
C7	0.10537 (12)	0.1023 (3)	0.11398 (16)	0.0429 (4)
C8	0.05590 (13)	0.1030 (4)	0.19698 (19)	0.0515 (5)
C9	0.51704 (11)	0.1302 (2)	0.18651 (15)	0.0372 (4)
C10	0.65028 (11)	0.1159 (2)	0.36438 (14)	0.0349 (3)
C11	0.67292 (11)	0.1056 (2)	0.48215 (14)	0.0366 (4)
C12	0.76552 (12)	0.0967 (3)	0.55291 (16)	0.0435 (4)
C13	0.83466 (12)	0.0983 (3)	0.50765 (16)	0.0446 (4)
C14	0.81081 (11)	0.1101 (2)	0.39143 (16)	0.0398 (4)
C15	0.71950 (12)	0.1205 (2)	0.31875 (15)	0.0385 (4)
N1	0.55488 (9)	0.1157 (2)	0.29736 (12)	0.0375 (3)
O1	0.38649 (8)	0.07391 (19)	0.29284 (10)	0.0458 (3)
O2	0.20269 (8)	0.08261 (18)	0.17686 (10)	0.0432 (3)
O3	0.60157 (9)	0.10408 (19)	0.52038 (11)	0.0462 (3)
Cl1	0.89826 (3)	0.10870 (7)	0.33413 (5)	0.05476 (17)
H1	0.5154 (16)	0.095 (3)	0.3294 (19)	0.057 (6)*
H3	0.6156 (16)	0.048 (3)	0.584 (2)	0.058 (6)*
H4	0.1662 (17)	0.112 (3)	−0.044 (2)	0.067 (7)*
H5	0.2700 (13)	0.157 (3)	−0.1342 (18)	0.048 (5)*
H6	0.4309 (14)	0.169 (3)	−0.0299 (16)	0.047 (5)*
H7A	0.0925 (14)	0.221 (3)	0.0713 (18)	0.055 (6)*
H7B	0.0851 (14)	−0.005 (3)	0.0600 (18)	0.049 (5)*
H8A	0.0771 (17)	0.197 (3)	0.250 (2)	0.067 (7)*
H8B	0.0646 (15)	−0.015 (4)	0.2363 (19)	0.063 (6)*
H8C	−0.0076 (18)	0.120 (3)	0.157 (2)	0.068 (7)*
H9	0.5538 (13)	0.150 (2)	0.1399 (16)	0.041 (5)*
H12	0.7798 (15)	0.087 (3)	0.633 (2)	0.055 (6)*
H13	0.8974 (15)	0.090 (3)	0.5585 (18)	0.053 (6)*
H15	0.7051 (13)	0.124 (3)	0.2410 (18)	0.046 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0326 (8)	0.0412 (8)	0.0316 (8)	0.0001 (7)	0.0127 (6)	−0.0005 (7)
C2	0.0332 (8)	0.0416 (8)	0.0302 (8)	0.0009 (7)	0.0124 (6)	0.0021 (6)
C3	0.0329 (8)	0.0404 (8)	0.0331 (8)	−0.0007 (7)	0.0122 (6)	−0.0005 (7)
C4	0.0356 (8)	0.0490 (9)	0.0333 (8)	0.0003 (7)	0.0081 (7)	−0.0003 (7)
C5	0.0454 (10)	0.0520 (11)	0.0264 (8)	0.0044 (8)	0.0103 (7)	0.0021 (7)
C6	0.0425 (9)	0.0470 (10)	0.0344 (9)	0.0034 (7)	0.0197 (7)	0.0042 (7)
C7	0.0294 (8)	0.0547 (11)	0.0421 (9)	0.0028 (8)	0.0099 (7)	0.0023 (9)
C8	0.0334 (9)	0.0712 (14)	0.0510 (11)	0.0059 (9)	0.0167 (9)	0.0038 (11)
C9	0.0349 (8)	0.0439 (9)	0.0368 (8)	−0.0001 (7)	0.0178 (7)	0.0027 (7)
C10	0.0298 (7)	0.0389 (8)	0.0367 (9)	−0.0004 (6)	0.0129 (6)	0.0021 (7)
C11	0.0352 (8)	0.0407 (8)	0.0373 (8)	0.0004 (7)	0.0172 (7)	0.0021 (7)
C12	0.0382 (9)	0.0533 (10)	0.0365 (9)	0.0016 (8)	0.0102 (7)	0.0024 (8)
C13	0.0312 (8)	0.0510 (10)	0.0475 (10)	0.0006 (7)	0.0091 (7)	0.0016 (8)
C14	0.0313 (8)	0.0409 (9)	0.0511 (10)	−0.0009 (7)	0.0197 (7)	0.0017 (8)
C15	0.0361 (8)	0.0447 (9)	0.0383 (9)	0.0008 (7)	0.0178 (7)	0.0007 (7)
N1	0.0295 (7)	0.0513 (8)	0.0334 (7)	−0.0013 (6)	0.0136 (6)	0.0017 (6)
O1	0.0332 (6)	0.0767 (9)	0.0287 (6)	−0.0018 (6)	0.0125 (5)	0.0055 (6)
O2	0.0277 (6)	0.0683 (8)	0.0333 (6)	−0.0003 (5)	0.0107 (5)	0.0035 (5)
O3	0.0403 (7)	0.0646 (8)	0.0403 (7)	0.0069 (6)	0.0225 (6)	0.0103 (6)
Cl1	0.0386 (2)	0.0643 (3)	0.0721 (3)	0.0028 (2)	0.0328 (2)	0.0067 (2)

Geometric parameters (Å, º) top

C1—C9	1.410 (2)	C8—H8C	0.93 (3)
C1—C6	1.421 (2)	C9—N1	1.310 (2)
C1—C2	1.432 (2)	C9—H9	0.96 (2)
C2—O1	1.279 (2)	C10—C15	1.384 (2)
C2—C3	1.445 (2)	C10—C11	1.399 (2)
C3—O2	1.363 (2)	C10—N1	1.408 (2)
C3—C4	1.371 (2)	C11—O3	1.3519 (19)
C4—C5	1.408 (3)	C11—C12	1.386 (2)
C4—H4	0.96 (2)	C12—C13	1.380 (3)
C5—C6	1.354 (2)	C12—H12	0.95 (2)
C5—H5	0.94 (2)	C13—C14	1.378 (3)
C6—H6	0.95 (2)	C13—H13	0.95 (2)
C7—O2	1.430 (2)	C14—C15	1.378 (2)
C7—C8	1.502 (3)	C14—Cl1	1.7456 (17)
C7—H7A	0.99 (2)	C15—H15	0.92 (2)
C7—H7B	1.00 (2)	N1—H1	0.86 (2)
C8—H8A	0.92 (2)	O3—H3	0.85 (2)
C8—H8B	0.97 (2)

C9—C1—C6	118.39 (15)	H8A—C8—H8C	109 (2)
C9—C1—C2	120.41 (15)	H8B—C8—H8C	108.4 (19)
C6—C1—C2	121.18 (14)	N1—C9—C1	123.47 (15)
O1—C2—C1	121.83 (14)	N1—C9—H9	121.9 (11)
O1—C2—C3	121.77 (14)	C1—C9—H9	114.6 (11)
C1—C2—C3	116.40 (14)	C15—C10—C11	120.52 (15)
O2—C3—C4	125.61 (15)	C15—C10—N1	123.16 (15)
O2—C3—C2	114.20 (14)	C11—C10—N1	116.29 (14)
C4—C3—C2	120.18 (15)	O3—C11—C12	123.59 (16)
C3—C4—C5	122.02 (16)	O3—C11—C10	117.09 (15)
C3—C4—H4	118.9 (14)	C12—C11—C10	119.32 (15)
C5—C4—H4	119.0 (14)	C13—C12—C11	120.32 (17)
C6—C5—C4	119.94 (16)	C13—C12—H12	121.3 (13)
C6—C5—H5	123.1 (12)	C11—C12—H12	118.4 (13)
C4—C5—H5	116.9 (12)	C14—C13—C12	119.38 (16)
C5—C6—C1	120.23 (16)	C14—C13—H13	122.5 (13)
C5—C6—H6	120.8 (12)	C12—C13—H13	118.1 (13)
C1—C6—H6	118.8 (12)	C15—C14—C13	121.78 (16)
O2—C7—C8	108.09 (15)	C15—C14—Cl1	118.87 (14)
O2—C7—H7A	110.6 (12)	C13—C14—Cl1	119.34 (13)
C8—C7—H7A	108.8 (12)	C14—C15—C10	118.66 (16)
O2—C7—H7B	108.1 (12)	C14—C15—H15	120.2 (12)
C8—C7—H7B	111.4 (12)	C10—C15—H15	121.0 (12)
H7A—C7—H7B	109.8 (17)	C9—N1—C10	127.35 (15)
C7—C8—H8A	111.7 (15)	C9—N1—H1	113.4 (15)
C7—C8—H8B	110.1 (14)	C10—N1—H1	119.0 (15)
H8A—C8—H8B	109 (2)	C3—O2—C7	116.33 (13)
C7—C8—H8C	109.0 (15)	C11—O3—H3	112.0 (16)

C9—C1—C2—O1	−2.2 (3)	C15—C10—C11—C12	−1.1 (3)
C6—C1—C2—O1	179.60 (16)	N1—C10—C11—C12	177.13 (16)
C9—C1—C2—C3	176.96 (15)	O3—C11—C12—C13	179.80 (17)
C6—C1—C2—C3	−1.3 (2)	C10—C11—C12—C13	0.1 (3)
O1—C2—C3—O2	2.8 (2)	C11—C12—C13—C14	0.5 (3)
C1—C2—C3—O2	−176.34 (14)	C12—C13—C14—C15	0.0 (3)
O1—C2—C3—C4	−178.42 (16)	C12—C13—C14—Cl1	−179.07 (14)
C1—C2—C3—C4	2.5 (2)	C13—C14—C15—C10	−1.0 (3)
O2—C3—C4—C5	176.54 (16)	Cl1—C14—C15—C10	178.08 (13)
C2—C3—C4—C5	−2.1 (3)	C11—C10—C15—C14	1.5 (3)
C3—C4—C5—C6	0.4 (3)	N1—C10—C15—C14	−176.58 (16)
C4—C5—C6—C1	0.8 (3)	C1—C9—N1—C10	177.28 (17)
C9—C1—C6—C5	−178.59 (17)	C15—C10—N1—C9	−4.2 (3)
C2—C1—C6—C5	−0.3 (3)	C11—C10—N1—C9	177.63 (17)
C6—C1—C9—N1	178.49 (16)	C4—C3—O2—C7	−4.7 (2)
C2—C1—C9—N1	0.2 (3)	C2—C3—O2—C7	174.00 (15)
C15—C10—C11—O3	179.17 (15)	C8—C7—O2—C3	−174.00 (16)
N1—C10—C11—O3	−2.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86 (2)	1.88 (2)	2.5957 (17)	140 (2)
N1—H1···O3	0.86 (2)	2.29 (2)	2.640 (2)	104.3 (17)
O3—H3···O1ⁱ	0.85 (2)	1.79 (2)	2.6258 (17)	165 (2)
C9—H9···O3ⁱⁱ	0.96 (2)	2.594 (19)	3.419 (2)	143.8 (14)

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄ClNO₃
M_r	291.72
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	15.4313 (7), 7.1710 (2), 12.6071 (6)
β (°)	111.168 (4)
V (Å³)	1300.94 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.30
Crystal size (mm)	0.52 × 0.29 × 0.09

Data collection
Diffractometer	STOE IPDS II diffractometer
Absorption correction	Integration X-RED32 (Stoe & Cie, 2002)
T_min, T_max	0.616, 0.927
No. of measured, independent and observed [I > 2σ(I)] reflections	15989, 2680, 2084
R_int	0.060
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.099, 1.05
No. of reflections	2680
No. of parameters	237
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.25

Computer programs: X-AREA (Stoe & Cie, 2002), X-AREA, X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86 (2)	1.88 (2)	2.5957 (17)	140 (2)
N1—H1···O3	0.86 (2)	2.29 (2)	2.640 (2)	104.3 (17)
O3—H3···O1ⁱ	0.85 (2)	1.79 (2)	2.6258 (17)	165 (2)
C9—H9···O3ⁱⁱ	0.96 (2)	2.594 (19)	3.419 (2)	143.8 (14)

Symmetry codes: (i) −x+1, −y, −z+1; (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. F.279 of the University Research Fund).

References

Büyükgüngör, O., Odabaşoğlu, M., Narayana, B., Vijesh, A. M. & Yathirajan, H. S. (2007). Acta Cryst. E63, o1996–o1998. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ersanlı, C. C., Albayrak, Ç., Odabaşoǧlu, M. & Erdönmez, A. (2003). Acta Cryst. C59, o601–o602. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Özek, A., Albayrak, Ç., Odabaşoğlu, M. & Büyükgüngör, O. (2007). Acta Cryst. C63, o177–o180. Web of Science CSD CrossRef IUCr Journals Google Scholar
Özek, A., Büyükgüngör, O., Albayrak, Ç. & Odabaşoğlu, M. (2008). Acta Cryst. E64, o1613–o1614. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany. Google Scholar
Tanak, H., Erşahin, F., Ağar, E. & Büyükgüngör, O. (2008). Anal. Sci. 24, 237–238. Web of Science PubMed Google Scholar

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Volume 65| Part 9| September 2009| Page o2153

doi:10.1107/S1600536809031298

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

(Z)-6-[(5-Chloro-2-hy­droxy­phenyl)­amino­methyl­ene]-2-eth­oxy­cyclo­hexa-2,4-dienone

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(Z)-6-[(5-Chloro-2-hydroxyphenyl)aminomethylene]-2-ethoxycyclohexa-2,4-dienone