Bis(2-hydroxy­benzaldehyde oxime) O,O′-butane-1,4-diyldicarbonyl ether

Etemadi, B.; Kia, R.; Sharghi, H.; Hosseini Sarvari, M.

doi:10.1107/S1600536809016663

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page o1309

doi:10.1107/S1600536809016663

Open

access

Bis(2-hydroxybenzaldehyde oxime) O,O′-butane-1,4-diyldicarbonyl ether

Bijan Etemadi,^a ^* Reza Kia,^a ‡ Hashem Sharghi ^b and Mona Hosseini Sarvari ^b

^aFaculty of Sciences, Department of Earth Sciences, Shiraz University, Shiraz, 71454, Iran, and ^bFaculty of Sciences, Chemistry Department, Shiraz University, Shiraz, 71454, Iran
^*Correspondence e-mail: etemadi_bi@yahoo.com

(Received 3 May 2009; accepted 4 May 2009; online 20 May 2009)

The molecule of the title compound, C₂₀H₂₀N₂O₆, lies across a crystallographic inversion centre, the asymmetric unit comprising one half-molecule. An intramolecular O—H⋯N hydrogen bond generates a six-membered ring, producing an S(6) ring motif. Pairs of intermolecular C—H⋯O hydrogen bonds link neighbouring molecules into a layer with R²₂(38) ring motif. The crystal structure is further stabilized by the intermolecular C—H⋯π interactions.

Related literature

For bond-length data, see Allen et al. (1987 ). For hydrogen bond motifs, see Bernstein et al. (1995 ). For Schiff bases, see: Granovski et al., (1993 ). For the synthesis, see: Hosseini Sarvari (2003 ).

Experimental

Crystal data

C₂₀H₂₀N₂O₆
M_r = 384.38
Monoclinic, C 2/c
a = 13.0293 (11) Å
b = 5.5464 (4) Å
c = 25.538 (2) Å
β = 91.348 (7)°
V = 1845.0 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 120 K
0.45 × 0.11 × 0.10 mm

Data collection

STOE IPDSII diffractometer
Absorption correction: numerical (X-RED32; Stoe & Cie (2005 ) T_min = 0.956, T_max = 0.985
10357 measured reflections
2493 independent reflections
2098 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.099
S = 1.10
2493 reflections
135 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.91 (3)	1.79 (3)	2.5836 (15)	144 (2)
C4—H4⋯O1ⁱ	0.93	2.45	3.1874 (17)	136
C2—H2⋯Cg1ⁱⁱ	0.93	2.75	3.4659 (14)	134
Symmetry codes: (i) $[x-{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (ii) $[x+1, -y-1, z-{\script{1\over 2}}]$ . Cg1 is the centroid of the C1–C6 benzene ring.

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA; data reduction: X-AREA; 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/S1600536809016663/at2778sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809016663/at2778Isup2.hkl

checkCIF report

Comment top

Schiff base compounds are some of the most important stereochemical models in transition metal coordination chemistry, with their ease of preparation and structural variations (Granovski et al., 1993). In continuation of our works on the synthesis and structural characterization of Schiff base ligands here we report the structure of the title compound.

The asymmetric unit of the title compound, Fig. 1, lies across a crystallographic inversion centre. Intramolecular O—H···N hydrogen bond generates a six-membered ring, producing an S(6) ring motif (Bernstein et al., 1995). Pairs of intermolecular C—H···O hydrogen bonds link neighbouring molecules into a layer with R²₂(38) ring motif (Fig. 2). The crystal structure is further stabilized by the intermolecular C—H···π interactions [Cg1 is the centroid of the C1–C6 benzene ring] (Table 1).

Related literature top

For bond-length data, see Allen et al. (1987). For hydrogen bond motifs, see Bernstein et al. (1995). For Schiff bases, see: Granovski et al., (1993). For the synthesis, see: Hosseini Sarvari (2003).Cg1 is the centroid of the C1–C6 benzene ring.

Experimental top

An ethyl acetate solution (40 ml) of salicylaldoxime (2 mmol, 768 mg) was treated with butanedicarboxylic acid chloride (1 mmol, 183 mg) at -5 ⁰ C. The mixture was stirred for 30 min and then filtered and the resulting white powder dried under air (Hosseini Sarvari, 2003). Single crystals suitable for X-ray diffraction were obtained from an ethanol solution.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA (Stoe & Cie, 2005); data reduction: X-AREA (Stoe & Cie, 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 molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atomic numbering. Intramolecular hydrogen bonds are shown as dashed lines. Symmetry code for A suffix: -x + 1/2, -y + 1/2, -z + 1].
	Fig. 2. The crystal packing of the title compound, showing linking of the molecules into a layer through R²₂(38) motifs. Intermolecular interactions are drawn as dashed lines.

Bis(2-hydroxybenzaldehyde oxime) O,O'-(butane-1,4-diyldicarbonyl) ether top

Crystal data top

C₂₀H₂₀N₂O₆	F(000) = 808
M_r = 384.38	D_x = 1.384 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1302 reflections
a = 13.0293 (11) Å	θ = 3.1–29.2°
b = 5.5464 (4) Å	µ = 0.10 mm⁻¹
c = 25.538 (2) Å	T = 120 K
β = 91.348 (7)°	Needle, colourless
V = 1845.0 (3) Å³	0.45 × 0.11 × 0.10 mm
Z = 4

Data collection top

STOE IPDS II diffractometer	2493 independent reflections
Radiation source: fine-focus sealed tube	2098 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.091
Detector resolution: 0.15 pixels mm^-1	θ_max = 29.2°, θ_min = 3.1°
rotation method scans	h = −17→17
Absorption correction: numerical (X-RED32; Stoe & Cie (2005)	k = −7→7
T_min = 0.956, T_max = 0.985	l = −35→34
41515 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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.099	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ²(F_o²) + (0.0425P)² + 1.8216P] where P = (F_o² + 2F_c²)/3
2493 reflections	(Δ/σ)_max = 0.004
135 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₂₀H₂₀N₂O₆	V = 1845.0 (3) Å³
M_r = 384.38	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 13.0293 (11) Å	µ = 0.10 mm⁻¹
b = 5.5464 (4) Å	T = 120 K
c = 25.538 (2) Å	0.45 × 0.11 × 0.10 mm
β = 91.348 (7)°

Data collection top

STOE IPDS II diffractometer	2493 independent reflections
Absorption correction: numerical (X-RED32; Stoe & Cie (2005)	2098 reflections with I > 2σ(I)
T_min = 0.956, T_max = 0.985	R_int = 0.091
41515 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.099	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	Δρ_max = 0.31 e Å⁻³
2493 reflections	Δρ_min = −0.20 e Å⁻³
135 parameters

Special details top

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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
C1	0.79600 (9)	−0.3740 (2)	0.32698 (5)	0.0186 (3)
C2	0.73433 (10)	−0.5276 (2)	0.29667 (5)	0.0204 (3)
H2	0.7620	−0.6677	0.2828	0.025*
C3	0.63188 (10)	−0.4721 (2)	0.28720 (5)	0.0206 (3)
H3	0.5909	−0.5768	0.2674	0.025*
C4	0.58953 (9)	−0.2610 (3)	0.30699 (5)	0.0212 (3)
H4	0.5207	−0.2245	0.3004	0.025*
C5	0.65095 (9)	−0.1061 (2)	0.33650 (5)	0.0192 (3)
H5	0.6230	0.0355	0.3495	0.023*
C6	0.75482 (9)	−0.1590 (2)	0.34720 (5)	0.0168 (2)
C7	0.81678 (10)	0.0064 (2)	0.37953 (5)	0.0193 (3)
H7	0.7866 (13)	0.154 (3)	0.3912 (7)	0.027 (4)*
C8	1.05836 (10)	0.0434 (2)	0.43627 (5)	0.0204 (3)
C9	1.11260 (10)	0.2321 (2)	0.46898 (5)	0.0208 (3)
H9A	1.0741	0.2617	0.5004	0.025*
H9B	1.1155	0.3816	0.4494	0.025*
C10	1.22133 (10)	0.1530 (2)	0.48435 (5)	0.0206 (3)
H10B	1.2588	0.1167	0.4529	0.025*
H10A	1.2181	0.0069	0.5051	0.025*
N1	0.90918 (8)	−0.0542 (2)	0.39115 (4)	0.0224 (3)
O1	0.89508 (7)	−0.4424 (2)	0.33553 (4)	0.0289 (3)
H1	0.9268 (18)	−0.333 (5)	0.3572 (10)	0.062 (7)*
O2	0.96033 (7)	0.11970 (18)	0.42331 (4)	0.0223 (2)
O3	1.09270 (8)	−0.14750 (19)	0.42343 (4)	0.0271 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0151 (5)	0.0196 (6)	0.0210 (6)	0.0028 (4)	−0.0008 (4)	0.0010 (5)
C2	0.0222 (6)	0.0177 (6)	0.0213 (6)	0.0026 (5)	0.0002 (5)	−0.0012 (5)
C3	0.0191 (6)	0.0219 (6)	0.0207 (6)	−0.0031 (5)	−0.0022 (4)	−0.0009 (5)
C4	0.0146 (5)	0.0261 (7)	0.0227 (6)	0.0016 (5)	−0.0013 (4)	−0.0001 (5)
C5	0.0172 (6)	0.0199 (6)	0.0204 (6)	0.0031 (5)	0.0011 (4)	−0.0008 (5)
C6	0.0163 (5)	0.0171 (6)	0.0170 (5)	−0.0003 (4)	−0.0008 (4)	0.0010 (5)
C7	0.0202 (6)	0.0185 (6)	0.0191 (6)	−0.0007 (5)	−0.0006 (4)	−0.0001 (5)
C8	0.0194 (6)	0.0224 (7)	0.0192 (6)	−0.0037 (5)	−0.0019 (4)	0.0009 (5)
C9	0.0209 (6)	0.0207 (6)	0.0206 (6)	−0.0033 (5)	−0.0025 (5)	−0.0011 (5)
C10	0.0204 (6)	0.0216 (6)	0.0197 (6)	−0.0032 (5)	−0.0035 (5)	−0.0012 (5)
N1	0.0197 (5)	0.0231 (6)	0.0241 (6)	−0.0047 (4)	−0.0043 (4)	−0.0052 (5)
O1	0.0170 (5)	0.0292 (6)	0.0402 (6)	0.0085 (4)	−0.0070 (4)	−0.0111 (5)
O2	0.0199 (5)	0.0217 (5)	0.0250 (5)	−0.0030 (4)	−0.0048 (4)	−0.0048 (4)
O3	0.0250 (5)	0.0231 (5)	0.0330 (5)	0.0006 (4)	−0.0067 (4)	−0.0060 (4)

Geometric parameters (Å, º) top

C1—O1	1.3583 (15)	C7—H7	0.958 (18)
C1—C2	1.3935 (18)	C8—O3	1.1985 (17)
C1—C6	1.4105 (18)	C8—O2	1.3784 (16)
C2—C3	1.3857 (17)	C8—C9	1.5047 (18)
C2—H2	0.9300	C9—C10	1.5255 (18)
C3—C4	1.3943 (19)	C9—H9A	0.9700
C3—H3	0.9300	C9—H9B	0.9700
C4—C5	1.3850 (18)	C10—C10ⁱ	1.526 (2)
C4—H4	0.9300	C10—H10B	0.9700
C5—C6	1.4054 (17)	C10—H10A	0.9700
C5—H5	0.9300	N1—O2	1.4226 (14)
C6—C7	1.4639 (17)	O1—H1	0.91 (3)
C7—N1	1.2782 (17)

O1—C1—C2	116.85 (12)	C6—C7—H7	119.1 (10)
O1—C1—C6	123.07 (12)	O3—C8—O2	123.73 (12)
C2—C1—C6	120.08 (11)	O3—C8—C9	126.36 (12)
C3—C2—C1	120.10 (12)	O2—C8—C9	109.91 (11)
C3—C2—H2	120.0	C8—C9—C10	111.35 (11)
C1—C2—H2	120.0	C8—C9—H9A	109.4
C2—C3—C4	120.75 (12)	C10—C9—H9A	109.4
C2—C3—H3	119.6	C8—C9—H9B	109.4
C4—C3—H3	119.6	C10—C9—H9B	109.4
C5—C4—C3	119.31 (11)	H9A—C9—H9B	108.0
C5—C4—H4	120.3	C9—C10—C10ⁱ	111.85 (14)
C3—C4—H4	120.3	C9—C10—H10B	109.2
C4—C5—C6	121.19 (12)	C10ⁱ—C10—H10B	109.2
C4—C5—H5	119.4	C9—C10—H10A	109.2
C6—C5—H5	119.4	C10ⁱ—C10—H10A	109.2
C5—C6—C1	118.56 (11)	H10B—C10—H10A	107.9
C5—C6—C7	119.65 (12)	C7—N1—O2	112.42 (11)
C1—C6—C7	121.79 (11)	C1—O1—H1	109.0 (15)
N1—C7—C6	118.03 (12)	C8—O2—N1	110.45 (10)
N1—C7—H7	122.9 (10)

O1—C1—C2—C3	178.68 (12)	C2—C1—C6—C7	179.53 (12)
C6—C1—C2—C3	−1.30 (19)	C5—C6—C7—N1	175.82 (12)
C1—C2—C3—C4	1.0 (2)	C1—C6—C7—N1	−3.07 (19)
C2—C3—C4—C5	−0.1 (2)	O3—C8—C9—C10	0.66 (19)
C3—C4—C5—C6	−0.6 (2)	O2—C8—C9—C10	179.67 (10)
C4—C5—C6—C1	0.30 (19)	C8—C9—C10—C10ⁱ	177.66 (13)
C4—C5—C6—C7	−178.63 (12)	C6—C7—N1—O2	−179.06 (10)
O1—C1—C6—C5	−179.35 (12)	O3—C8—O2—N1	−2.57 (18)
C2—C1—C6—C5	0.63 (18)	C9—C8—O2—N1	178.39 (10)
O1—C1—C6—C7	−0.4 (2)	C7—N1—O2—C8	178.03 (11)

Symmetry code: (i) −x+5/2, −y+1/2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.91 (3)	1.79 (3)	2.5836 (15)	144 (2)
C4—H4···O1ⁱⁱ	0.93	2.45	3.1874 (17)	136
C2—H2···Cg1ⁱⁱⁱ	0.93	2.75	3.4659 (14)	134

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

Experimental details

Crystal data
Chemical formula	C₂₀H₂₀N₂O₆
M_r	384.38
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	120
a, b, c (Å)	13.0293 (11), 5.5464 (4), 25.538 (2)
β (°)	91.348 (7)
V (Å³)	1845.0 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.45 × 0.11 × 0.10

Data collection
Diffractometer	STOE IPDS II diffractometer
Absorption correction	Numerical (X-RED32; Stoe & Cie (2005)
T_min, T_max	0.956, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	41515, 2493, 2098
R_int	0.091
(sin θ/λ)_max (Å⁻¹)	0.687

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.099, 1.10
No. of reflections	2493
No. of parameters	135
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.20

Computer programs: X-AREA (Stoe & Cie, 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	0.91 (3)	1.79 (3)	2.5836 (15)	144 (2)
C4—H4···O1ⁱ	0.9300	2.4500	3.1874 (17)	136.00
C2—H2···Cg1ⁱⁱ	0.93	2.75	3.4659 (14)	134

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

Footnotes

‡Thomson Reuters ResearcherID: A-5471-2009.

Acknowledgements

We thank Shiraz University for financial support.

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–S19. CrossRef Web of Science Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chamg, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Granovski, A. D., Nivorozhkin, A. L. & Minkin, V. I. (1993). Coord. Chem. Rev. 126, 1–69. Google Scholar
Hosseini Sarvari, M. (2003). Ph. D. Thesis, Shiraz University. 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
Stoe & Cie (2005). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany. Google Scholar