(Z)-6-[(5-Chloro-2-hydroxy­anilino)­methyl­ene]-4-methoxy­cyclo­hexa-2,4-dienone 0.25-hydrate

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

doi:10.1107/S160053680901410X

organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page o1104

doi:10.1107/S160053680901410X

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(Z)-6-[(5-Chloro-2-hydroxyanilino)methylene]-4-methoxycyclohexa-2,4-dienone 0.25-hydrate

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

^aDepartment of Physics, Ondokuz Mayıs University, TR-55139 Samsun, Turkey, ^bFaculty of Education, Sinop University, Turkey, and ^cPamukkale University, Denizli Technical Vocational School, Turkey
^*Correspondence e-mail: orhanb@omu.edu.tr

(Received 30 March 2009; accepted 15 April 2009; online 25 April 2009)

The title compound, C₁₄H₁₂ClNO₃·0.25H₂O, exists in the keto–amine form, and the aromatic rings are oriented at a dihedral angle of 7.24 (7)°. Bifurcated intramolecular N—H⋯(O,O) hydrogen bonds result in the formation of planar six- and five-membered rings. In the crystal structure, intermolecular O—H⋯O and C—H⋯O hydrogen bonds link the molecules into chains. π–π contacts between benzene rings [centroid–centroid distance = 3.5065 (9) Å] may further stabilize the structure. There also exists a weak C—H⋯π interaction.

Related literature

For general background, see: Büyükgüngör et al. (2007 ); Hökelek et al. (2004 ); Odabaşoğlu et al. (2004 ). For related structures, see: Özek et al. (2007 , 2008 ); Ersanlı et al. (2003 ).

Experimental

Crystal data

C₁₄H₁₂ClNO₃·0.25H₂O
M_r = 279.95
Monoclinic, C 2/c
a = 21.3670 (11) Å
b = 6.7600 (3) Å
c = 17.7404 (9) Å
β = 103.841 (4)°
V = 2488.0 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 100 K
0.68 × 0.54 × 0.41 mm

Data collection

Stoe IPDS-II diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ) T_min = 0.970, T_max = 0.970
6976 measured reflections
2588 independent reflections
2352 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.086
S = 1.09
2588 reflections
186 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.31 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	1.84	2.5511 (16)	140
N1—H1⋯O3	0.86	2.19	2.6063 (17)	109
C3—H3⋯O4	0.93	2.43	3.279 (5)	151
O4—H4A⋯O2ⁱ	0.831 (19)	2.029 (19)	2.842 (3)	166 (6)
O3—H3A⋯O1ⁱⁱ	0.852 (17)	1.743 (18)	2.5652 (16)	162 (3)
C12—H12⋯O2ⁱⁱⁱ	0.93	2.56	3.4372 (18)	157
C7—H7A⋯Cg1^iv	0.96	2.83	3.644 (2)	143
Symmetry codes: (i) x, y-1, z; (ii) $[-x+{\script{3\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (iii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iv) $[x+{\script{1\over 2}}, y+{\script{3\over 2}}, z]$ . Cg1 is the centroid of the C1–C6 ring.

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-RED32 (Stoe & Cie, 2002); 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 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680901410X/hk2658sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680901410X/hk2658Isup2.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 herein the crystal structure of the title compound.

In general, o-hydroxy Schiff bases exhibit two possible tautomeric forms, namely, phenol-imine and keto-amine. In the solid state, the keto-amine form is observed in naphthaldimine (Odabaşoǧlu et al., 2004), while the phenol-imine form is observed in salicylaldimine (Büyükgüngör et al., 2007) Schiff bases. However, naphthaldimine and salicylaldimine can also exist in the phenol-imine and keto-amine forms, respectively depending on the stereochemistry of the molecule and the type of nitrogen substituents in naphthaldimine and salicylaldimine Schiff bases (Hökelek et al., 2004).

In the title compound (Fig. 1), the keto-amine form is favored over the phenol-imine form, as indicated by C2—O1 [1.2924 (18) Å], C8—N1 [1.3122 (19) Å], C1—C8 [1.412 (2) Å] and C1—C2 [1.433 (2) Å] bonds. The C2—O1 and C8—N1 bonds indicate double-bond and a high degree of single-bond characters, respectively. 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 (C9—C14) is 7.24 (7)°. Intramolecular N—H···O hydrogen bonds (Table 1) result in the formations of planar six- and five-membered rings C (O1/N1/C1/C2/C8/H1) and D (O3/N1/C9/C10/H1). They are oriented with respect to the adjacent rings at dihedral angles of A/C = 4.44 (9), A/D = 9.6 (9), B/C = 5.42 (9), B/D = 2.96 (9) and C/D = 6.55 (9)°. So, they are nearly coplanar.

In the crystal structure, intermolecular O—H···O and C—H···O hydrogen bonds (Table 1) link the molecules into chains (Fig. 2), in which they may be effective in the stabilization of the structure. The π–π contact between the phenyl rings, Cg1—Cg2ⁱ [symmetry code: (i) 1/2 - x, 3/2 - y, -z, where Cg1 and Cg2 are centroids of the rings A (C1—C6) and B (C9—C14), respectively] may further stabilize the structure, with centroid-centroid distance of 3.5065 (9) Å. There also exists a weak C—H···π interaction (Table 1).

Related literature top

For general background, see: Büyükgüngör et al. (2007); Hökelek et al. (2004); Odabaşoǧlu et al. (2004). For related structures, see: Özek et al. (2007, 2008); Ersanlı et al. (2003).

Experimental top

For the preparation of the title compound, the mixture of 5-methoxysalicyl- aldehyde (0.5 g, 3.3 mmol) in ethanol (20 ml) and 2-hydroxy-5-chloroaniline (0.47 g, 3.3 mmol) in ethanol (20 ml) was stirred for 1 h under reflux. Crystals suitable for X-ray analysis were obtained from methanol by slow evaporation (yield; % 84, m.p. 415–416 K).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-RED32 (Stoe & Cie, 2002); 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) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Hydrogen bonds are shown as dashed lines.
	Fig. 2. A partial packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.

(Z)-6-[(5-Chloro-2-hydroxyanilino)methylene]-4-methoxycyclohexa- 2,4-dienone 0.25-hydrate top

Crystal data top

C₁₄H₁₂ClNO₃·0.25H₂O	F(000) = 1162
M_r = 279.95	D_x = 1.495 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 6976 reflections
a = 21.3670 (11) Å	θ = 2.0–28.0°
b = 6.7600 (3) Å	µ = 0.31 mm⁻¹
c = 17.7404 (9) Å	T = 100 K
β = 103.841 (4)°	Prism, red
V = 2488.0 (2) Å³	0.68 × 0.54 × 0.41 mm
Z = 8

Data collection top

Stoe IPDS-II diffractometer	2588 independent reflections
Radiation source: fine-focus sealed tube	2352 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.022
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.5°, θ_min = 2.0°
ω scans	h = −25→26
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −8→7
T_min = 0.970, T_max = 0.970	l = −22→22
6976 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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.086	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ²(F_o²) + (0.0376P)² + 3.3917P] where P = (F_o² + 2F_c²)/3
2588 reflections	(Δ/σ)_max = 0.001
186 parameters	Δρ_max = 0.28 e Å⁻³
2 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₁₄H₁₂ClNO₃·0.25H₂O	V = 2488.0 (2) Å³
M_r = 279.95	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 21.3670 (11) Å	µ = 0.31 mm⁻¹
b = 6.7600 (3) Å	T = 100 K
c = 17.7404 (9) Å	0.68 × 0.54 × 0.41 mm
β = 103.841 (4)°

Data collection top

Stoe IPDS-II diffractometer	2588 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	2352 reflections with I > 2σ(I)
T_min = 0.970, T_max = 0.970	R_int = 0.022
6976 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	2 restraints
wR(F²) = 0.086	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	Δρ_max = 0.28 e Å⁻³
2588 reflections	Δρ_min = −0.31 e Å⁻³
186 parameters

Special details top

Experimental. 141 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	Occ. (<1)
C1	0.64391 (7)	0.8209 (2)	0.49336 (8)	0.0163 (3)
C2	0.63352 (7)	0.6614 (2)	0.43854 (8)	0.0171 (3)
C3	0.58193 (7)	0.6836 (2)	0.37118 (9)	0.0191 (3)
H3	0.5736	0.5834	0.3342	0.023*
C4	0.54480 (7)	0.8493 (2)	0.36036 (8)	0.0189 (3)
H4	0.5112	0.8593	0.3162	0.023*
C5	0.55578 (7)	1.0069 (2)	0.41439 (8)	0.0175 (3)
C6	0.60491 (7)	0.9945 (2)	0.47962 (8)	0.0170 (3)
H6	0.6129	1.0986	0.5149	0.020*
C7	0.51514 (8)	1.3060 (2)	0.45380 (9)	0.0211 (3)
H7A	0.5063	1.2434	0.4987	0.032*
H7B	0.4832	1.4055	0.4349	0.032*
H7C	0.5570	1.3663	0.4675	0.032*
C8	0.69160 (7)	0.8057 (2)	0.56359 (8)	0.0164 (3)
H8	0.6987	0.9125	0.5976	0.020*
C9	0.77299 (7)	0.6029 (2)	0.65047 (8)	0.0158 (3)
C10	0.79878 (7)	0.4110 (2)	0.65524 (9)	0.0181 (3)
C11	0.84717 (7)	0.3589 (2)	0.71999 (9)	0.0201 (3)
H11	0.8645	0.2321	0.7238	0.024*
C12	0.86950 (7)	0.4950 (2)	0.77875 (8)	0.0190 (3)
H12	0.9020	0.4604	0.8218	0.023*
C13	0.84290 (7)	0.6831 (2)	0.77270 (8)	0.0175 (3)
C14	0.79444 (7)	0.7395 (2)	0.70949 (8)	0.0172 (3)
H14	0.7767	0.8657	0.7066	0.021*
Cl1	0.873014 (18)	0.85790 (6)	0.84450 (2)	0.02270 (12)
N1	0.72613 (6)	0.64456 (19)	0.58204 (7)	0.0165 (3)
H1	0.7192	0.5522	0.5477	0.020*
O1	0.66836 (5)	0.50302 (16)	0.45048 (6)	0.0219 (3)
O2	0.51359 (5)	1.16195 (17)	0.39490 (6)	0.0229 (3)
O3	0.77355 (5)	0.28754 (18)	0.59629 (7)	0.0236 (3)
H3A	0.7990 (11)	0.196 (3)	0.5898 (15)	0.055 (8)*
O4	0.5000	0.3573 (10)	0.2500	0.0253 (14)	0.25
H4A	0.500 (4)	0.286 (5)	0.2880 (13)	0.03 (2)*	0.25

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0144 (7)	0.0192 (7)	0.0150 (6)	−0.0005 (6)	0.0028 (5)	−0.0001 (6)
C2	0.0154 (7)	0.0190 (7)	0.0166 (7)	0.0000 (6)	0.0033 (5)	−0.0010 (6)
C3	0.0184 (7)	0.0226 (8)	0.0155 (7)	−0.0012 (6)	0.0023 (6)	−0.0039 (6)
C4	0.0166 (7)	0.0262 (8)	0.0127 (7)	−0.0004 (6)	0.0012 (5)	0.0000 (6)
C5	0.0158 (7)	0.0202 (7)	0.0167 (7)	0.0021 (6)	0.0043 (5)	0.0017 (6)
C6	0.0173 (7)	0.0187 (7)	0.0147 (6)	0.0001 (6)	0.0037 (5)	−0.0016 (5)
C7	0.0221 (8)	0.0180 (7)	0.0213 (7)	0.0030 (6)	0.0017 (6)	−0.0009 (6)
C8	0.0142 (7)	0.0192 (7)	0.0161 (7)	−0.0004 (6)	0.0045 (5)	−0.0018 (6)
C9	0.0119 (6)	0.0217 (7)	0.0139 (6)	0.0004 (6)	0.0031 (5)	0.0008 (6)
C10	0.0165 (7)	0.0194 (7)	0.0180 (7)	0.0003 (6)	0.0031 (6)	−0.0021 (6)
C11	0.0178 (7)	0.0196 (7)	0.0220 (7)	0.0035 (6)	0.0030 (6)	0.0025 (6)
C12	0.0153 (7)	0.0245 (8)	0.0158 (7)	0.0016 (6)	0.0011 (5)	0.0043 (6)
C13	0.0143 (7)	0.0235 (8)	0.0146 (7)	−0.0019 (6)	0.0035 (5)	−0.0017 (6)
C14	0.0158 (7)	0.0183 (7)	0.0166 (7)	0.0018 (6)	0.0021 (5)	0.0009 (6)
Cl1	0.0219 (2)	0.0258 (2)	0.01674 (19)	0.00025 (14)	−0.00266 (14)	−0.00406 (14)
N1	0.0151 (6)	0.0184 (6)	0.0142 (6)	0.0007 (5)	0.0001 (5)	−0.0018 (5)
O1	0.0205 (5)	0.0206 (6)	0.0221 (5)	0.0040 (4)	0.0002 (4)	−0.0053 (4)
O2	0.0226 (6)	0.0233 (6)	0.0189 (5)	0.0078 (4)	−0.0030 (4)	−0.0015 (4)
O3	0.0206 (6)	0.0228 (6)	0.0238 (6)	0.0049 (5)	−0.0016 (4)	−0.0077 (5)
O4	0.036 (4)	0.021 (3)	0.016 (3)	0.000	−0.001 (3)	0.000

Geometric parameters (Å, º) top

C1—C8	1.412 (2)	C8—H8	0.9300
C1—C6	1.426 (2)	C9—C14	1.389 (2)
C1—C2	1.433 (2)	C9—C10	1.404 (2)
C2—O1	1.2924 (18)	C9—N1	1.4050 (18)
C2—C3	1.427 (2)	C10—O3	1.3459 (18)
C3—C4	1.359 (2)	C10—C11	1.395 (2)
C3—H3	0.9300	C11—C12	1.387 (2)
C4—C5	1.415 (2)	C11—H11	0.9300
C4—H4	0.9300	C12—C13	1.386 (2)
C5—C6	1.366 (2)	C12—H12	0.9300
C5—O2	1.3720 (18)	C13—C14	1.385 (2)
C6—H6	0.9300	C13—Cl1	1.7438 (15)
C7—O2	1.4229 (19)	C14—H14	0.9300
C7—H7A	0.9600	N1—H1	0.8600
C7—H7B	0.9600	O3—H3A	0.852 (17)
C7—H7C	0.9600	O4—H4A	0.831 (19)
C8—N1	1.3122 (19)

C8—C1—C6	118.69 (13)	N1—C8—H8	119.2
C8—C1—C2	120.36 (14)	C1—C8—H8	119.2
C6—C1—C2	120.91 (13)	C14—C9—C10	120.98 (13)
O1—C2—C3	121.57 (14)	C14—C9—N1	123.82 (13)
O1—C2—C1	121.51 (13)	C10—C9—N1	115.19 (13)
C3—C2—C1	116.90 (14)	O3—C10—C11	124.28 (14)
C4—C3—C2	120.85 (14)	O3—C10—C9	116.60 (13)
C4—C3—H3	119.6	C11—C10—C9	119.10 (14)
C2—C3—H3	119.6	C12—C11—C10	120.35 (14)
C3—C4—C5	121.89 (13)	C12—C11—H11	119.8
C3—C4—H4	119.1	C10—C11—H11	119.8
C5—C4—H4	119.1	C13—C12—C11	119.30 (13)
C6—C5—O2	125.86 (14)	C13—C12—H12	120.3
C6—C5—C4	119.79 (14)	C11—C12—H12	120.3
O2—C5—C4	114.34 (12)	C14—C13—C12	121.88 (14)
C5—C6—C1	119.64 (14)	C14—C13—Cl1	118.58 (12)
C5—C6—H6	120.2	C12—C13—Cl1	119.49 (11)
C1—C6—H6	120.2	C13—C14—C9	118.37 (14)
O2—C7—H7A	109.5	C13—C14—H14	120.8
O2—C7—H7B	109.5	C9—C14—H14	120.8
H7A—C7—H7B	109.5	C8—N1—C9	128.60 (13)
O2—C7—H7C	109.5	C8—N1—H1	115.7
H7A—C7—H7C	109.5	C9—N1—H1	115.7
H7B—C7—H7C	109.5	C5—O2—C7	116.07 (11)
N1—C8—C1	121.66 (14)	C10—O3—H3A	114.0 (18)

C8—C1—C2—O1	−2.1 (2)	C14—C9—C10—C11	−0.7 (2)
C6—C1—C2—O1	−179.69 (14)	N1—C9—C10—C11	177.86 (14)
C8—C1—C2—C3	176.39 (14)	O3—C10—C11—C12	−178.82 (15)
C6—C1—C2—C3	−1.2 (2)	C9—C10—C11—C12	−0.1 (2)
O1—C2—C3—C4	178.48 (14)	C10—C11—C12—C13	0.5 (2)
C1—C2—C3—C4	0.0 (2)	C11—C12—C13—C14	0.0 (2)
C2—C3—C4—C5	0.6 (2)	C11—C12—C13—Cl1	−177.44 (12)
C3—C4—C5—C6	0.0 (2)	C12—C13—C14—C9	−0.9 (2)
C3—C4—C5—O2	−179.47 (14)	Cl1—C13—C14—C9	176.63 (11)
O2—C5—C6—C1	178.19 (14)	C10—C9—C14—C13	1.2 (2)
C4—C5—C6—C1	−1.2 (2)	N1—C9—C14—C13	−177.27 (14)
C8—C1—C6—C5	−175.82 (14)	C1—C8—N1—C9	−176.94 (14)
C2—C1—C6—C5	1.8 (2)	C14—C9—N1—C8	−5.5 (2)
C6—C1—C8—N1	175.38 (14)	C10—C9—N1—C8	175.95 (14)
C2—C1—C8—N1	−2.3 (2)	C6—C5—O2—C7	−10.6 (2)
C14—C9—C10—O3	178.07 (14)	C4—C5—O2—C7	168.79 (13)
N1—C9—C10—O3	−3.3 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86	1.84	2.5511 (16)	140
N1—H1···O3	0.86	2.19	2.6063 (17)	109
C3—H3···O4	0.93	2.43	3.279 (5)	151
O4—H4A···O2ⁱ	0.83 (2)	2.03 (2)	2.842 (3)	166 (6)
O3—H3A···O1ⁱⁱ	0.85 (2)	1.74 (2)	2.5652 (16)	162 (3)
C12—H12···O2ⁱⁱⁱ	0.93	2.56	3.4372 (18)	157
C7—H7A···Cg1^iv	0.96	2.83	3.644 (2)	143

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₂ClNO₃·0.25H₂O
M_r	279.95
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	21.3670 (11), 6.7600 (3), 17.7404 (9)
β (°)	103.841 (4)
V (Å³)	2488.0 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.31
Crystal size (mm)	0.68 × 0.54 × 0.41

Data collection
Diffractometer	Stoe IPDS-II diffractometer
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.970, 0.970
No. of measured, independent and observed [I > 2σ(I)] reflections	6976, 2588, 2352
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.086, 1.09
No. of reflections	2588
No. of parameters	186
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.31

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), 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	1.84	2.5511 (16)	139.5
N1—H1···O3	0.86	2.19	2.6063 (17)	109.1
C3—H3···O4	0.93	2.43	3.279 (5)	151.3
O4—H4A···O2ⁱ	0.831 (19)	2.029 (19)	2.842 (3)	166 (6)
O3—H3A···O1ⁱⁱ	0.852 (17)	1.743 (18)	2.5652 (16)	162 (3)
C12—H12···O2ⁱⁱⁱ	0.93	2.56	3.4372 (18)	156.5
C7—H7A···Cg1^iv	0.96	2.834	3.644 (2)	142.64

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

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the 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
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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
Hökelek, T., Bilge, S., Demiriz, Ş., Özgüç, B. & Kılıç, Z. (2004). Acta Cryst. C60, o803–o805. Web of Science CSD CrossRef IUCr Journals Google Scholar
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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
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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(Z)-6-[(5-Chloro-2-hy­droxy­anilino)­methyl­ene]-4-meth­oxy­cyclo­hexa-2,4-dienone 0.25-hydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(Z)-6-[(5-Chloro-2-hydroxyanilino)methylene]-4-methoxycyclohexa-2,4-dienone 0.25-hydrate