6,6′-Dieth­oxy-2,2′-[4,5-dimethyl-o-phenyl­enebis(nitrilo­methyl­idyne)]diphenol–ethanol–water (1/1/1)

Kargar, H.; Kia, R.; Jamshidvand, A.; Fun, H.-K.

doi:10.1107/S1600536809008903

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 4| April 2009| Pages o776-o777

doi:10.1107/S1600536809008903

Open

access

6,6′-Diethoxy-2,2′-[4,5-dimethyl-o-phenylenebis(nitrilomethylidyne)]diphenol–ethanol–water (1/1/1)

Hadi Kargar,^a Reza Kia,^b ‡ Arezoo Jamshidvand ^a and Hoong-Kun Fun ^b ^*

^aDepartment of Chemistry, School of Science, Payame Noor University (PNU), Ardakan, Yazd, Iran, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 9 March 2009; accepted 11 March 2009; online 14 March 2009)

The title bis-Schiff base compound, C₂₆H₂₈N₂O₄·C₂H₆O·H₂O, crystallizes as an ethanol and water solvate. Strong intramolecular O—H⋯N hydrogen bonds generate S(6) ring motifs. The water H atoms form bifurcated O—H⋯(O,O) intermolecular hydrogen bonds with the O atoms of the hydroxyl and ethoxy groups with R₁²(5) ring motifs, which may, in part, influence the molecular configuration. The dihedral angles between the central benzene ring and the two outer benzene rings of the Schiff base molecule are 5.64 (8) and 44.78 (9)°. The crystal structure is further stabilized by intermolecular C—H⋯O and π–π interactions [centroid–centroid distances = 3.6139 (11)–3.7993 (11) Å].

Related literature

For bond-length data, see: Allen et al. (1987 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For related structures, see, for example: Cakir et al. (2002 ); Eltayeb et al. (2007a ,b ); Karabıyık et al. (2007 ); Fun & Kia (2008 ); Fun, Kargar & Kia (2008 ); Fun, Kia & Kargar (2008 ). For applications of Schiff base ligands, see, for example: Hajioudis et al. (1987 ); Granovski et al. (1993 ); Dao et al. (2000 ); Shahrokhian et al. (2000 ); Eltayeb & Ahmed (2005a ,b ); Fakhari et al. (2005 ); Karthikeyan et al. (2006 ); Sriram et al. (2006 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₆H₂₈N₂O₄·C₂H₆O·H₂O
M_r = 496.59
Monoclinic, P 2₁ /n
a = 9.5095 (5) Å
b = 25.6633 (12) Å
c = 10.7766 (5) Å
β = 99.177 (2)°
V = 2596.3 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.45 × 0.12 × 0.02 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.961, T_max = 0.999
32813 measured reflections
7595 independent reflections
4303 reflections with I > 2σ(I)
R_int = 0.068

Refinement

R[F² > 2σ(F²)] = 0.066
wR(F²) = 0.160
S = 1.03
7595 reflections
341 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.51 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.84	1.84	2.584 (2)	146
O2—H2⋯N2	0.84	1.87	2.609 (2)	146
O1W—H1W1⋯O2ⁱ	0.86 (3)	2.24 (3)	2.947 (2)	139 (3)
O1W—H1W1⋯O4ⁱ	0.86 (3)	2.28 (3)	3.018 (2)	145 (3)
O1W—H2W1⋯O1ⁱ	0.78 (3)	2.30 (3)	3.061 (2)	166 (3)
O1W—H2W1⋯O3ⁱ	0.78 (3)	2.43 (3)	2.967 (2)	127 (3)
O5—H5⋯O1Wⁱⁱ	0.84	1.82	2.659 (3)	179
C7—H7A⋯O5	0.95	2.33	3.242 (3)	162
Symmetry codes: (i) x+1, y, z; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809008903/lh2786sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809008903/lh2786Isup2.hkl

checkCIF report

Comment top

Schiff bases have received much attention because of their potential applications with some of these compounds exhibiting various pharmacological activities, such as anticancer (Dao et al., 2000), anti-HIV (Sriram et al., 2006), antibacterial and antifungal (Karthikeyan et al., 2006) properties. Although numerous transition-metal complexes of Schiff bases have been structurally characterized (Granovski et al., 1993), relatively few free Schiff bases have been similarly characterized. N-substituted salicylaldimines show photochromism and thermochromism in the solid state. These effects are produced by intramolecular proton transfer associated with a change in the π-electron configuration (Hadjioudis et al. 1987). In addition, some of them may be used as analytical reagents for the determination of trace elements (Eltayeb & Ahmed, 2005a,b) such as nickel in some natural food products (Fakhari et al., 2005) or biologically important species (Shahrokhian et al., 2000). As part of a general study of tetradenate and bidentate Schiff bases (Fun, Kargar & Kia 2008; Fun, Kia & Kargar 2008), we determined the structure of the title compound.

The asymmetric unit of the title compound, Fig. 1, comprises a Schiff base ligand, an ethanol and a water molecule of crystallization. All bonds lengths agree with standard values (Allen et al., 1987). Strong intramolecular O—H···N hydrogen bonds generate S(6) ring motifs (Bernstein et al., 1995). The hydrogen atoms of the water molecule make bifurcated intermolecular hydrogen bonds with the oxygen atoms of the hydroxyl and ethoxy groups with R²₁(5) ring motifs (Bernstein et al., 1995), which may, in part, influence the molecular configuration (Table 1). The dihedral angles between the central benzene ring and the two outer benzene rings of the Schiff base are 5.64 (8) and 44.78 (9)° which shows one of the outer benzene ring is twisted. The crystal structure is further stabilized by intermolecular C—H···O and π-π interactions [Cg1···Cg1ⁱⁱⁱ = 3.6139 (11) Å, (iii) x - 1/2, 1/2 - y, z - 1/2; Cg2···Cg2^iv = 3.7993 (11) Å, (iv) -x, -y, z - 1; Cg1 and Cg2 are the centroids of the C1–C6 and C15–C20 benzene rings].

Related literature top

For bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For related structures, see, for example: Cakir et al. (2002); Eltayeb et al. (2007a,b); Karabıyık et al. (2007); Fun & Kia (2008); Fun, Kargar & Kia (2008); Fun, Kia & Kargar (2008). For applications of Schiff base ligands, see, for example: Hajioudis et al. (1987); Granovski et al. (1993); Dao et al. (2000); Shahrokhian et al. (2000); Eltayeb & Ahmed (2005a,b); Fakhari et al. (2005); Karthikeyan et al. (2006); Sriram et al. (2006). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental top

The title compound was synthesized by adding 3-ethoxy-salicylaldehyde (4 mmol) to a solution of 4,5-dimethyl-o-phenylenediamine (2 mmol) in ethanol (20 ml). The mixture was refluxed with stirring for half an hour. The resultant yellow solution was filtered. Yellow single crystals of the title compound suitable for X-ray structure determination were recrystallized from ethanol by slow evaporation of the solvents at room temperature over several days.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

Fig. 1. The asymmetric unit of the title compound, showing 50% probability displacement ellipsoids and the atomic numbering. Intra- and intermolecular hydrogen bonds are drawn as dashed lines.

6,6'-Diethoxy-2,2'-[4,5-dimethyl-o- phenylenebis(nitrilomethylidyne)]diphenol–ethanol–water (1/1/1) top

Crystal data top

C₂₆H₂₈N₂O₄·C₂H₆O·H₂O	F(000) = 1064
M_r = 496.59	D_x = 1.270 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4281 reflections
a = 9.5095 (5) Å	θ = 2.3–27.2°
b = 25.6633 (12) Å	µ = 0.09 mm⁻¹
c = 10.7766 (5) Å	T = 100 K
β = 99.177 (2)°	Plate, orange
V = 2596.3 (2) Å³	0.45 × 0.12 × 0.02 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	7595 independent reflections
Radiation source: fine-focus sealed tube	4303 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.068
ϕ and ω scans	θ_max = 30.1°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −13→13
T_min = 0.961, T_max = 0.999	k = −36→32
32813 measured reflections	l = −14→15

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.160	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0637P)² + 0.5228P] where P = (F_o² + 2F_c²)/3
7595 reflections	(Δ/σ)_max < 0.001
341 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.51 e Å⁻³

Crystal data top

C₂₆H₂₈N₂O₄·C₂H₆O·H₂O	V = 2596.3 (2) Å³
M_r = 496.59	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.5095 (5) Å	µ = 0.09 mm⁻¹
b = 25.6633 (12) Å	T = 100 K
c = 10.7766 (5) Å	0.45 × 0.12 × 0.02 mm
β = 99.177 (2)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	7595 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	4303 reflections with I > 2σ(I)
T_min = 0.961, T_max = 0.999	R_int = 0.068
32813 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.066	0 restraints
wR(F²) = 0.160	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.38 e Å⁻³
7595 reflections	Δρ_min = −0.51 e Å⁻³
341 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
O1	−0.06040 (14)	0.16561 (5)	0.35336 (13)	0.0257 (3)
H1	0.0253	0.1707	0.3841	0.039*
O2	0.13555 (14)	0.07045 (5)	0.28857 (12)	0.0261 (3)
H2	0.1782	0.0973	0.3193	0.039*
O3	−0.33019 (13)	0.16242 (5)	0.25794 (12)	0.0250 (3)
O4	−0.00004 (14)	−0.01584 (5)	0.22724 (12)	0.0276 (3)
O5	0.1829 (2)	0.38301 (7)	0.43926 (18)	0.0696 (7)
H5	0.2336	0.3938	0.5052	0.104*
N1	0.16852 (16)	0.21898 (6)	0.42494 (13)	0.0202 (3)
N2	0.30447 (16)	0.12535 (6)	0.45335 (14)	0.0221 (4)
C1	−0.12615 (19)	0.21183 (7)	0.32673 (16)	0.0195 (4)
C2	−0.2720 (2)	0.21128 (7)	0.27477 (17)	0.0212 (4)
C3	−0.3428 (2)	0.25763 (8)	0.24528 (17)	0.0239 (4)
H3A	−0.4410	0.2573	0.2103	0.029*
C4	−0.2710 (2)	0.30517 (8)	0.26650 (18)	0.0271 (5)
H4A	−0.3207	0.3369	0.2456	0.032*
C5	−0.1292 (2)	0.30622 (8)	0.31737 (17)	0.0241 (4)
H5A	−0.0812	0.3387	0.3319	0.029*
C6	−0.0546 (2)	0.25953 (7)	0.34807 (16)	0.0197 (4)
C7	0.0960 (2)	0.26133 (8)	0.39833 (16)	0.0216 (4)
H7A	0.1422	0.2941	0.4120	0.026*
C8	0.31619 (19)	0.21948 (7)	0.47186 (16)	0.0195 (4)
C9	0.3962 (2)	0.26478 (8)	0.50515 (17)	0.0222 (4)
H9A	0.3501	0.2977	0.4944	0.027*
C10	0.5406 (2)	0.26294 (7)	0.55340 (16)	0.0212 (4)
C11	0.6084 (2)	0.21406 (8)	0.56871 (17)	0.0216 (4)
C12	0.5301 (2)	0.16936 (8)	0.53558 (16)	0.0222 (4)
H12A	0.5768	0.1365	0.5447	0.027*
C13	0.3845 (2)	0.17112 (7)	0.48914 (16)	0.0207 (4)
C14	0.3273 (2)	0.08414 (7)	0.52055 (17)	0.0236 (4)
H14A	0.3939	0.0857	0.5962	0.028*
C15	0.2554 (2)	0.03506 (8)	0.48551 (17)	0.0229 (4)
C16	0.2757 (2)	−0.00817 (8)	0.56692 (18)	0.0279 (5)
H16A	0.3398	−0.0056	0.6439	0.033*
C17	0.2041 (2)	−0.05394 (8)	0.53627 (19)	0.0287 (5)
H17A	0.2191	−0.0829	0.5917	0.034*
C18	0.1087 (2)	−0.05798 (8)	0.42326 (19)	0.0270 (4)
H18A	0.0579	−0.0895	0.4029	0.032*
C19	0.0884 (2)	−0.01644 (7)	0.34162 (17)	0.0232 (4)
C20	0.16074 (19)	0.03062 (7)	0.37184 (17)	0.0208 (4)
C21	−0.47745 (19)	0.15886 (8)	0.20175 (18)	0.0262 (4)
H21A	−0.4913	0.1729	0.1151	0.031*
H21B	−0.5377	0.1790	0.2515	0.031*
C22	−0.5166 (2)	0.10202 (8)	0.20022 (19)	0.0310 (5)
H22A	−0.6166	0.0978	0.1622	0.047*
H22B	−0.5027	0.0887	0.2865	0.047*
H22C	−0.4559	0.0826	0.1510	0.047*
C23	−0.0850 (2)	−0.06146 (8)	0.1942 (2)	0.0305 (5)
H23A	−0.1449	−0.0689	0.2592	0.037*
H23B	−0.0231	−0.0920	0.1869	0.037*
C24	−0.1771 (3)	−0.05042 (9)	0.0699 (2)	0.0410 (6)
H24A	−0.2390	−0.0804	0.0451	0.061*
H24B	−0.1166	−0.0441	0.0059	0.061*
H24C	−0.2358	−0.0196	0.0778	0.061*
C25	0.6220 (2)	0.31263 (8)	0.58803 (19)	0.0276 (5)
H25A	0.5559	0.3422	0.5782	0.041*
H25B	0.6935	0.3174	0.5328	0.041*
H25C	0.6694	0.3106	0.6756	0.041*
C26	0.7651 (2)	0.21015 (8)	0.62075 (18)	0.0279 (5)
H26A	0.7960	0.1738	0.6173	0.042*
H26B	0.7816	0.2222	0.7082	0.042*
H26C	0.8195	0.2319	0.5705	0.042*
C27	0.0836 (4)	0.45876 (12)	0.3369 (3)	0.0799 (11)
H27A	0.0918	0.4816	0.2655	0.120*
H27B	0.0995	0.4791	0.4148	0.120*
H27C	−0.0118	0.4433	0.3258	0.120*
C28	0.1892 (3)	0.41771 (13)	0.3437 (2)	0.0575 (8)
H28A	0.1756	0.3986	0.2629	0.069*
H28B	0.2852	0.4337	0.3553	0.069*
O1W	0.84548 (19)	0.08448 (7)	0.14875 (16)	0.0412 (4)
H1W1	0.920 (3)	0.0656 (11)	0.169 (3)	0.064 (9)*
H2W1	0.855 (3)	0.1065 (13)	0.199 (3)	0.076 (11)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0167 (6)	0.0236 (7)	0.0347 (8)	0.0002 (6)	−0.0026 (6)	0.0009 (6)
O2	0.0295 (8)	0.0200 (7)	0.0262 (7)	−0.0036 (6)	−0.0031 (6)	0.0021 (6)
O3	0.0155 (6)	0.0262 (8)	0.0318 (7)	0.0000 (6)	−0.0008 (5)	−0.0009 (6)
O4	0.0285 (7)	0.0219 (7)	0.0291 (7)	−0.0042 (6)	−0.0058 (6)	−0.0017 (6)
O5	0.0928 (16)	0.0370 (11)	0.0628 (13)	−0.0105 (10)	−0.0368 (11)	0.0001 (9)
N1	0.0185 (8)	0.0257 (9)	0.0163 (7)	−0.0007 (7)	0.0022 (6)	−0.0002 (6)
N2	0.0210 (8)	0.0214 (9)	0.0230 (8)	−0.0016 (7)	0.0012 (7)	−0.0028 (6)
C1	0.0194 (9)	0.0234 (10)	0.0158 (8)	0.0027 (8)	0.0030 (7)	−0.0003 (7)
C2	0.0195 (9)	0.0257 (11)	0.0185 (9)	0.0005 (8)	0.0035 (7)	−0.0015 (7)
C3	0.0197 (9)	0.0326 (11)	0.0191 (9)	0.0035 (8)	0.0027 (7)	0.0008 (8)
C4	0.0274 (11)	0.0256 (11)	0.0283 (10)	0.0083 (9)	0.0048 (8)	0.0031 (8)
C5	0.0267 (10)	0.0220 (10)	0.0240 (9)	0.0011 (8)	0.0054 (8)	−0.0004 (8)
C6	0.0208 (9)	0.0255 (10)	0.0136 (8)	0.0018 (8)	0.0046 (7)	−0.0007 (7)
C7	0.0229 (10)	0.0238 (10)	0.0182 (9)	−0.0029 (8)	0.0036 (7)	−0.0008 (7)
C8	0.0196 (9)	0.0248 (10)	0.0141 (8)	−0.0014 (8)	0.0030 (7)	−0.0007 (7)
C9	0.0248 (10)	0.0229 (10)	0.0192 (9)	−0.0010 (8)	0.0042 (8)	−0.0009 (7)
C10	0.0234 (9)	0.0262 (10)	0.0146 (8)	−0.0059 (8)	0.0050 (7)	−0.0012 (7)
C11	0.0190 (9)	0.0297 (11)	0.0172 (8)	−0.0036 (8)	0.0056 (7)	−0.0021 (8)
C12	0.0210 (9)	0.0255 (10)	0.0198 (9)	0.0018 (8)	0.0022 (7)	−0.0006 (8)
C13	0.0229 (9)	0.0233 (10)	0.0162 (8)	−0.0014 (8)	0.0039 (7)	−0.0020 (7)
C14	0.0196 (9)	0.0291 (11)	0.0211 (9)	−0.0006 (8)	−0.0005 (8)	−0.0018 (8)
C15	0.0198 (9)	0.0241 (10)	0.0243 (9)	−0.0004 (8)	0.0018 (8)	−0.0009 (8)
C16	0.0274 (10)	0.0277 (11)	0.0269 (10)	0.0032 (9)	−0.0005 (8)	0.0040 (8)
C17	0.0295 (11)	0.0252 (11)	0.0302 (10)	0.0032 (9)	0.0015 (9)	0.0052 (8)
C18	0.0255 (10)	0.0203 (10)	0.0348 (11)	−0.0004 (8)	0.0038 (9)	−0.0005 (8)
C19	0.0199 (9)	0.0239 (10)	0.0253 (9)	0.0014 (8)	0.0015 (8)	−0.0026 (8)
C20	0.0196 (9)	0.0191 (10)	0.0238 (9)	0.0010 (8)	0.0039 (8)	−0.0007 (7)
C21	0.0162 (9)	0.0386 (12)	0.0226 (9)	−0.0009 (9)	−0.0009 (7)	−0.0001 (8)
C22	0.0208 (10)	0.0402 (13)	0.0317 (11)	−0.0052 (9)	0.0030 (9)	−0.0031 (9)
C23	0.0278 (11)	0.0227 (11)	0.0389 (11)	−0.0052 (9)	−0.0009 (9)	−0.0054 (9)
C24	0.0407 (13)	0.0367 (13)	0.0400 (12)	−0.0085 (11)	−0.0106 (11)	−0.0076 (10)
C25	0.0259 (10)	0.0299 (11)	0.0268 (10)	−0.0085 (9)	0.0033 (8)	−0.0021 (8)
C26	0.0209 (10)	0.0366 (12)	0.0256 (10)	−0.0027 (9)	0.0024 (8)	−0.0043 (9)
C27	0.081 (2)	0.0466 (18)	0.093 (2)	−0.0021 (17)	−0.044 (2)	−0.0018 (16)
C28	0.0434 (15)	0.096 (2)	0.0340 (13)	−0.0122 (16)	0.0109 (12)	−0.0044 (14)
O1W	0.0394 (10)	0.0386 (10)	0.0406 (9)	0.0105 (8)	−0.0088 (8)	−0.0115 (8)

Geometric parameters (Å, º) top

O1—C1	1.350 (2)	C14—H14A	0.9500
O1—H1	0.8400	C15—C20	1.404 (2)
O2—C20	1.356 (2)	C15—C16	1.409 (3)
O2—H2	0.8400	C16—C17	1.372 (3)
O3—C2	1.371 (2)	C16—H16A	0.9500
O3—C21	1.437 (2)	C17—C18	1.401 (3)
O4—C19	1.377 (2)	C17—H17A	0.9500
O4—C23	1.435 (2)	C18—C19	1.376 (3)
O5—C28	1.370 (3)	C18—H18A	0.9500
O5—H5	0.8400	C19—C20	1.403 (3)
N1—C7	1.295 (2)	C21—C22	1.505 (3)
N1—C8	1.415 (2)	C21—H21A	0.9900
N2—C14	1.281 (2)	C21—H21B	0.9900
N2—C13	1.419 (2)	C22—H22A	0.9800
C1—C6	1.402 (3)	C22—H22B	0.9800
C1—C2	1.411 (2)	C22—H22C	0.9800
C2—C3	1.379 (3)	C23—C24	1.506 (3)
C3—C4	1.399 (3)	C23—H23A	0.9900
C3—H3A	0.9500	C23—H23B	0.9900
C4—C5	1.373 (3)	C24—H24A	0.9800
C4—H4A	0.9500	C24—H24B	0.9800
C5—C6	1.405 (3)	C24—H24C	0.9800
C5—H5A	0.9500	C25—H25A	0.9800
C6—C7	1.448 (3)	C25—H25B	0.9800
C7—H7A	0.9500	C25—H25C	0.9800
C8—C13	1.399 (3)	C26—H26A	0.9800
C8—C9	1.404 (3)	C26—H26B	0.9800
C9—C10	1.390 (3)	C26—H26C	0.9800
C9—H9A	0.9500	C27—C28	1.449 (4)
C10—C11	1.408 (3)	C27—H27A	0.9800
C10—C25	1.507 (3)	C27—H27B	0.9800
C11—C12	1.383 (3)	C27—H27C	0.9800
C11—C26	1.510 (3)	C28—H28A	0.9900
C12—C13	1.396 (3)	C28—H28B	0.9900
C12—H12A	0.9500	O1W—H1W1	0.86 (3)
C14—C15	1.454 (3)	O1W—H2W1	0.78 (3)

C1—O1—H1	109.5	C19—C18—C17	120.25 (18)
C20—O2—H2	109.5	C19—C18—H18A	119.9
C2—O3—C21	117.35 (14)	C17—C18—H18A	119.9
C19—O4—C23	116.90 (15)	C18—C19—O4	125.77 (17)
C28—O5—H5	109.5	C18—C19—C20	120.33 (17)
C7—N1—C8	122.35 (16)	O4—C19—C20	113.90 (16)
C14—N2—C13	119.64 (15)	O2—C20—C19	117.85 (16)
O1—C1—C6	122.41 (16)	O2—C20—C15	122.49 (17)
O1—C1—C2	117.93 (16)	C19—C20—C15	119.67 (17)
C6—C1—C2	119.66 (17)	O3—C21—C22	106.80 (16)
O3—C2—C3	125.94 (17)	O3—C21—H21A	110.4
O3—C2—C1	114.33 (16)	C22—C21—H21A	110.4
C3—C2—C1	119.73 (18)	O3—C21—H21B	110.4
C2—C3—C4	120.48 (17)	C22—C21—H21B	110.4
C2—C3—H3A	119.8	H21A—C21—H21B	108.6
C4—C3—H3A	119.8	C21—C22—H22A	109.5
C5—C4—C3	120.33 (18)	C21—C22—H22B	109.5
C5—C4—H4A	119.8	H22A—C22—H22B	109.5
C3—C4—H4A	119.8	C21—C22—H22C	109.5
C4—C5—C6	120.30 (18)	H22A—C22—H22C	109.5
C4—C5—H5A	119.9	H22B—C22—H22C	109.5
C6—C5—H5A	119.9	O4—C23—C24	107.00 (17)
C1—C6—C5	119.50 (17)	O4—C23—H23A	110.3
C1—C6—C7	120.96 (17)	C24—C23—H23A	110.3
C5—C6—C7	119.52 (17)	O4—C23—H23B	110.3
N1—C7—C6	121.07 (17)	C24—C23—H23B	110.3
N1—C7—H7A	119.5	H23A—C23—H23B	108.6
C6—C7—H7A	119.5	C23—C24—H24A	109.5
C13—C8—C9	118.63 (17)	C23—C24—H24B	109.5
C13—C8—N1	116.93 (16)	H24A—C24—H24B	109.5
C9—C8—N1	124.41 (17)	C23—C24—H24C	109.5
C10—C9—C8	122.02 (18)	H24A—C24—H24C	109.5
C10—C9—H9A	119.0	H24B—C24—H24C	109.5
C8—C9—H9A	119.0	C10—C25—H25A	109.5
C9—C10—C11	118.72 (17)	C10—C25—H25B	109.5
C9—C10—C25	120.09 (18)	H25A—C25—H25B	109.5
C11—C10—C25	121.19 (17)	C10—C25—H25C	109.5
C12—C11—C10	119.47 (17)	H25A—C25—H25C	109.5
C12—C11—C26	119.94 (18)	H25B—C25—H25C	109.5
C10—C11—C26	120.59 (17)	C11—C26—H26A	109.5
C11—C12—C13	121.84 (18)	C11—C26—H26B	109.5
C11—C12—H12A	119.1	H26A—C26—H26B	109.5
C13—C12—H12A	119.1	C11—C26—H26C	109.5
C12—C13—C8	119.30 (17)	H26A—C26—H26C	109.5
C12—C13—N2	121.93 (17)	H26B—C26—H26C	109.5
C8—C13—N2	118.71 (16)	C28—C27—H27A	109.5
N2—C14—C15	122.55 (17)	C28—C27—H27B	109.5
N2—C14—H14A	118.7	H27A—C27—H27B	109.5
C15—C14—H14A	118.7	C28—C27—H27C	109.5
C20—C15—C16	118.99 (17)	H27A—C27—H27C	109.5
C20—C15—C14	120.42 (17)	H27B—C27—H27C	109.5
C16—C15—C14	120.55 (17)	O5—C28—C27	113.5 (3)
C17—C16—C15	120.73 (18)	O5—C28—H28A	108.9
C17—C16—H16A	119.6	C27—C28—H28A	108.9
C15—C16—H16A	119.6	O5—C28—H28B	108.9
C16—C17—C18	120.03 (18)	C27—C28—H28B	108.9
C16—C17—H17A	120.0	H28A—C28—H28B	107.7
C18—C17—H17A	120.0	H1W1—O1W—H2W1	103 (3)

C21—O3—C2—C3	1.6 (3)	C26—C11—C12—C13	178.89 (17)
C21—O3—C2—C1	−178.13 (16)	C11—C12—C13—C8	2.0 (3)
O1—C1—C2—O3	0.3 (2)	C11—C12—C13—N2	179.06 (17)
C6—C1—C2—O3	179.82 (16)	C9—C8—C13—C12	−1.7 (3)
O1—C1—C2—C3	−179.47 (16)	N1—C8—C13—C12	−179.82 (16)
C6—C1—C2—C3	0.1 (3)	C9—C8—C13—N2	−178.84 (16)
O3—C2—C3—C4	−179.69 (17)	N1—C8—C13—N2	3.0 (2)
C1—C2—C3—C4	0.0 (3)	C14—N2—C13—C12	40.6 (3)
C2—C3—C4—C5	−0.2 (3)	C14—N2—C13—C8	−142.33 (18)
C3—C4—C5—C6	0.3 (3)	C13—N2—C14—C15	−176.25 (17)
O1—C1—C6—C5	179.54 (16)	N2—C14—C15—C20	2.6 (3)
C2—C1—C6—C5	0.0 (3)	N2—C14—C15—C16	−175.16 (19)
O1—C1—C6—C7	1.1 (3)	C20—C15—C16—C17	−0.2 (3)
C2—C1—C6—C7	−178.44 (17)	C14—C15—C16—C17	177.60 (19)
C4—C5—C6—C1	−0.2 (3)	C15—C16—C17—C18	−0.4 (3)
C4—C5—C6—C7	178.27 (18)	C16—C17—C18—C19	1.1 (3)
C8—N1—C7—C6	178.76 (16)	C17—C18—C19—O4	178.80 (19)
C1—C6—C7—N1	0.0 (3)	C17—C18—C19—C20	−1.2 (3)
C5—C6—C7—N1	−178.43 (17)	C23—O4—C19—C18	4.2 (3)
C7—N1—C8—C13	−175.89 (16)	C23—O4—C19—C20	−175.79 (17)
C7—N1—C8—C9	6.1 (3)	C18—C19—C20—O2	−179.31 (18)
C13—C8—C9—C10	0.6 (3)	O4—C19—C20—O2	0.6 (2)
N1—C8—C9—C10	178.60 (17)	C18—C19—C20—C15	0.6 (3)
C8—C9—C10—C11	0.2 (3)	O4—C19—C20—C15	−179.42 (17)
C8—C9—C10—C25	−179.88 (17)	C16—C15—C20—O2	−179.95 (18)
C9—C10—C11—C12	0.0 (3)	C14—C15—C20—O2	2.2 (3)
C25—C10—C11—C12	−179.86 (17)	C16—C15—C20—C19	0.1 (3)
C9—C10—C11—C26	179.99 (17)	C14—C15—C20—C19	−177.71 (18)
C25—C10—C11—C26	0.1 (3)	C2—O3—C21—C22	−177.08 (16)
C10—C11—C12—C13	−1.2 (3)	C19—O4—C23—C24	177.06 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.84	1.84	2.584 (2)	146
O1W—H1W1···O2ⁱ	0.86 (3)	2.24 (3)	2.947 (2)	139 (3)
O1W—H1W1···O4ⁱ	0.86 (3)	2.28 (3)	3.018 (2)	145 (3)
O2—H2···N2	0.84	1.87	2.609 (2)	146
O1W—H2W1···O1ⁱ	0.78 (3)	2.30 (3)	3.061 (2)	166 (3)
O1W—H2W1···O3ⁱ	0.78 (3)	2.43 (3)	2.967 (2)	127 (3)
O5—H5···O1Wⁱⁱ	0.84	1.82	2.659 (3)	179
C7—H7A···O5	0.95	2.33	3.242 (3)	162

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

Experimental details

Crystal data
Chemical formula	C₂₆H₂₈N₂O₄·C₂H₆O·H₂O
M_r	496.59
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	9.5095 (5), 25.6633 (12), 10.7766 (5)
β (°)	99.177 (2)
V (Å³)	2596.3 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.45 × 0.12 × 0.02

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.961, 0.999
No. of measured, independent and observed [I > 2σ(I)] reflections	32813, 7595, 4303
R_int	0.068
(sin θ/λ)_max (Å⁻¹)	0.705

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.066, 0.160, 1.03
No. of reflections	7595
No. of parameters	341
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.51

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.84	1.84	2.584 (2)	146
O1W—H1W1···O2ⁱ	0.86 (3)	2.24 (3)	2.947 (2)	139 (3)
O1W—H1W1···O4ⁱ	0.86 (3)	2.28 (3)	3.018 (2)	145 (3)
O2—H2···N2	0.84	1.87	2.609 (2)	146
O1W—H2W1···O1ⁱ	0.78 (3)	2.30 (3)	3.061 (2)	166 (3)
O1W—H2W1···O3ⁱ	0.78 (3)	2.43 (3)	2.967 (2)	127 (3)
O5—H5···O1Wⁱⁱ	0.84	1.82	2.659 (3)	179
C7—H7A···O5	0.95	2.33	3.242 (3)	162

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

Footnotes

‡Additional correspondance author, e-mail: zsrkk@yahoo.com.

Acknowledgements

HKF and RK thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. RK thanks Universiti Sains Malaysia for a post-doctoral research fellowship. HK and AJ thank PNU for financial support. HKF also thanks Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cakir, O., Elerman, Y. & Elmali, A. (2002). Anal. Sci. 18, 377. Web of Science CSD CrossRef PubMed Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Dao, V.-T., Gaspard, C., Mayer, M., Werner, G. H., Nguyen, S. N. & Michelot, R. J. (2000). Eur. J. Med. Chem. 35, 805–813. Web of Science CrossRef PubMed CAS Google Scholar
Eltayeb, N. E. & Ahmed, T. A. (2005a). J. Sci. Technol. 6, 51–59. Google Scholar
Eltayeb, N. E. & Ahmed, T. A. (2005b). Sudan J. Basic Sci. 7, 97–108. Google Scholar
Eltayeb, N. E., Teoh, S. G., Chantrapromma, S., Fun, H.-K. & Ibrahim, K. (2007a). Acta Cryst. E63, o3094–o3095. Web of Science CSD CrossRef IUCr Journals Google Scholar
Eltayeb, N. E., Teoh, S. G., Chantrapromma, S., Fun, H.-K. & Ibrahim, K. (2007b). Acta Cryst. E63, o3234–o3235. Web of Science CSD CrossRef IUCr Journals Google Scholar
Fakhari, A. R., Khorrami, A. R. & Naeimi, H. (2005). Talanta, 66, 813–817. Web of Science CrossRef PubMed CAS Google Scholar
Fun, H.-K., Kargar, H. & Kia, R. (2008). Acta Cryst. E64, o1308. Web of Science CSD CrossRef IUCr Journals Google Scholar
Fun, H.-K. & Kia, R. (2008). Acta Cryst. E64, o1657–o1658. Web of Science CSD CrossRef IUCr Journals Google Scholar
Fun, H.-K., Kia, R. & Kargar, H. (2008). Acta Cryst. E64, o1335. Web of Science CSD CrossRef IUCr Journals Google Scholar
Granovski, A. D., Nivorozhkin, A. L. & Minkin, V. I. (1993). Coord. Chem. Rev. 126, 1–69. Google Scholar
Hajioudis, E., Vitterakis, M. & Mustakali-Mavridis, I. (1987). Tetrahedron, 43, 1345–1351. Google Scholar
Karabıyık, H., Güzel, B., Aygün, M., Boğa, G. & Büyükgüngör, O. (2007). Acta Cryst. C63, o215–o218. Web of Science CSD CrossRef IUCr Journals Google Scholar
Karthikeyan, M. S., Prasad, D. J., Poojary, B., Bhat, K. S., Holla, B. S. & Kumari, N. S. (2006). Bioorg. Med. Chem. 14, 7482–7489. Web of Science CrossRef PubMed CAS Google Scholar
Shahrokhian, S., Amini, M. K., Kia, R. & Tangestaninejad, S. (2000). Anal. Chem. 72, 956–962. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sriram, D., Yogeeswari, P., Myneedu, N. S. & Saraswat, V. (2006). Bioorg. Med. Chem. Lett. 16, 2127–2129. Web of Science CrossRef PubMed CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 4| April 2009| Pages o776-o777

doi:10.1107/S1600536809008903

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

6,6′-Dieth­­oxy-2,2′-[4,5-di­methyl-o-phenyl­enebis(nitrilo­methyl­­idyne)]diphenol–ethanol–water (1/1/1)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

6,6′-Diethoxy-2,2′-[4,5-dimethyl-o-phenylenebis(nitrilomethylidyne)]diphenol–ethanol–water (1/1/1)