4-Hy­droxy­benzamide 1,4-dioxane hemisolvate

Srinu Tothadi; Gautam R Desiraju

doi:10.1107/S160053681203437X

. 2012 Aug 8;68(Pt 9):o2661. doi: 10.1107/S160053681203437X

4-Hydroxybenzamide 1,4-dioxane hemisolvate

Srinu Tothadi ^a, Gautam R Desiraju ^a,^*

PMCID: PMC3435686 PMID: 22969557

Abstract

The asymmetric unit of the title compound, C₇H₇NO₂·0.5C₄H₈O₂, is composed of one 4-hydroxybenzamide molecule and half of a 1,4-dioxane molecule. The complete dioxin molecule is generated by crystallographic inversion symmetry. The crystal has an extensive system of hydrogen bonds, in which the three donor H atoms are fully utilized: these result in amide–amide homodimers, and N—H⋯O(dioxane) and O—H⋯O(amide) links.

Related literature

For the structure and properties of 4-hydroxybenzamide and its hydrate, see: Kashino et al. (1991 ▶); Perlovich et al. (2007 ▶); Hansen et al. (2007 ▶).

Experimental

Crystal data

C₇H₇NO₂·0.5C₄H₈O₂
M _r = 181.19
Monoclinic,
a = 5.4062 (15) Å
b = 14.530 (3) Å
c = 12.027 (2) Å
β = 113.117 (10)°
V = 868.9 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 150 K
0.30 × 0.30 × 0.20 mm

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer
Absorption correction: multi-scan (REQAB; Jacobson, 1998 ▶) T _min = 0.969, T _max = 0.979
9077 measured reflections
1987 independent reflections
1841 reflections with I > 2σ(I)
R _int = 0.064

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.111
S = 1.01
1987 reflections
162 parameters
All H-atom parameters refined
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: CrystalClear-SM Expert (Rigaku, 2009 ▶); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1999 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681203437X/fy2064sup1.cif

e-68-o2661-sup1.cif^{(21.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681203437X/fy2064Isup2.hkl

e-68-o2661-Isup2.hkl^{(95.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681203437X/fy2064Isup3.cdx

Supplementary material file. DOI: 10.1107/S160053681203437X/fy2064Isup4.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H5⋯O1ⁱ	0.893 (18)	2.050 (18)	2.9349 (16)	170.8 (16)
N1—H6⋯O3ⁱⁱ	0.895 (19)	2.057 (19)	2.9171 (16)	161 (2)
O2—H9⋯O1ⁱⁱⁱ	0.909 (19)	1.78 (2)	2.6808 (14)	173 (2)

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

ST thanks UGC for a SRF and GRD thanks the DST for the award of a J. C. Bose fellowship. The authors thank the Rigaku Corporation, Tokyo, for their support through a generous loan of a Rigaku Mercury375R/M CCD (XtaLAB mini) diffractometer.

supplementary crystallographic information

Comment

Hydroxybenzamides and their derivates are extensively used as starting materials in the synthesis of fine chemicals and agrochemicals (Perlovich et al., 2007). Their physicochemical properties are recurrently studied in environmental and biological systems in descriptions of transport and metabolism. The molecular structure of the title compound is shown in Figure 1. In the solvated crystal, molecules are linked by amide···amide homodimers and other O—H···O and N—H···O synthons. The dioxane molecules form a channel along the a axis. Their position in the channel is stabilized by N—H···O hydrogen-bonded synthons (Figure 2).

Experimental

Crystals of the title compound were obtained by slow evaporation of a saturated solution of 4-hydroxybenzamide in 1,4-dioxane at ambient temperature. Good diffraction quality crystals were obtained after five days.