4-Hy­droxy­benzamide 1,4-dioxane hemisolvate

Tothadi, S.; Desiraju, G.R.

doi:10.1107/S160053681203437X

organic compounds

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ISSN: 2056-9890

Volume 68| Part 9| September 2012| Page o2661

doi:10.1107/S160053681203437X

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4-Hydroxybenzamide 1,4-dioxane hemisolvate

Srinu Tothadi ^a and Gautam R. Desiraju ^a ^*

^aSolid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560 012, India
^*Correspondence e-mail: desiraju@sscu.iisc.ernet.in

(Received 6 July 2012; accepted 2 August 2012; online 8 August 2012)

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, P 2₁ /c
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[F² > 2σ(F²)] = 0.039
wR(F²) = 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

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)
Symmetry codes: (i) -x+1, -y+2, -z+2; (ii) x, y+1, z; (iii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681203437X/fy2064sup1.cif

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

Supporting information file. DOI: 10.1107/S160053681203437X/fy2064Isup3.cdx

Supporting information file. DOI: 10.1107/S160053681203437X/fy2064Isup4.cml

checkCIF report

Comment top

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).

Related literature top

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 top

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.

Computing details top

Data collection: CrystalClear-SM Expert (Rigaku, 2009); cell refinement: CrystalClear-SM Expert (Rigaku, 2009); data reduction: CrystalClear-SM Expert (Rigaku, 2009); 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).

Figures top

	Fig. 1. The structure of title the compound with atom labels and 50% probability displacement ellipsoids.
	Fig. 2. O—H···O, N—H···O supramolecular synthons and amide···amide homodimers in the crystal structure.

4-Hydroxybenzamide 1,4-dioxane hemisolvate top

Crystal data top

C₇H₇NO₂·0.5C₄H₈O₂	F(000) = 384
M_r = 181.19	D_x = 1.385 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2599 reflections
a = 5.4062 (15) Å	θ = 3.4–27.5°
b = 14.530 (3) Å	µ = 0.11 mm⁻¹
c = 12.027 (2) Å	T = 150 K
β = 113.117 (10)°	Block, colourless
V = 868.9 (3) Å³	0.30 × 0.30 × 0.20 mm
Z = 4

Data collection top

Rigaku Mercury375R (2x2 bin mode) diffractometer	1987 independent reflections
Radiation source: fine-focus sealed tube	1841 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.064
profile data from ω–scans	θ_max = 27.5°, θ_min = 3.4°
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	h = −7→7
T_min = 0.969, T_max = 0.979	k = −18→18
9077 measured reflections	l = −15→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)] = 0.039	Hydrogen site location: difference Fourier map
wR(F²) = 0.111	All H-atom parameters refined
S = 1.01	w = 1/[σ²(F_o²) + (0.059P)² + 0.2987P] where P = (F_o² + 2F_c²)/3
1987 reflections	(Δ/σ)_max = 0.028
162 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₇H₇NO₂·0.5C₄H₈O₂	V = 868.9 (3) Å³
M_r = 181.19	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.4062 (15) Å	µ = 0.11 mm⁻¹
b = 14.530 (3) Å	T = 150 K
c = 12.027 (2) Å	0.30 × 0.30 × 0.20 mm
β = 113.117 (10)°

Data collection top

Rigaku Mercury375R (2x2 bin mode) diffractometer	1987 independent reflections
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	1841 reflections with I > 2σ(I)
T_min = 0.969, T_max = 0.979	R_int = 0.064
9077 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.111	All H-atom parameters refined
S = 1.01	Δρ_max = 0.28 e Å⁻³
1987 reflections	Δρ_min = −0.22 e Å⁻³
162 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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	0.80614 (16)	0.92851 (6)	1.04228 (7)	0.0225 (2)
O2	1.18374 (17)	0.64369 (6)	0.74199 (8)	0.0260 (3)
N1	0.5317 (2)	0.97339 (7)	0.85611 (9)	0.0239 (3)
C1	0.7279 (2)	0.92062 (7)	0.93018 (10)	0.0188 (3)
C2	0.8467 (2)	0.85033 (7)	0.87597 (10)	0.0188 (3)
C3	0.6951 (2)	0.80863 (8)	0.76593 (10)	0.0223 (3)
C4	0.8032 (2)	0.73933 (8)	0.71972 (10)	0.0221 (3)
C5	1.0678 (2)	0.71106 (8)	0.78283 (10)	0.0198 (3)
C6	1.2219 (2)	0.75283 (8)	0.89296 (10)	0.0233 (3)
C7	1.1109 (2)	0.82067 (8)	0.93947 (10)	0.0222 (3)
O3	0.24469 (18)	−0.02513 (7)	0.59392 (8)	0.0324 (3)
C8	0.0104 (3)	0.04862 (11)	0.40326 (13)	0.0355 (4)
C9	0.2203 (3)	0.05905 (9)	0.52870 (12)	0.0294 (4)
H5	0.442 (3)	1.0084 (12)	0.8887 (15)	0.033 (4)*
H6	0.481 (4)	0.9703 (13)	0.7759 (17)	0.043 (5)*
H7	1.217 (3)	0.8496 (11)	1.0151 (15)	0.032 (4)*
H8	1.405 (3)	0.7330 (11)	0.9349 (14)	0.032 (4)*
H9	1.060 (4)	0.6223 (13)	0.6709 (17)	0.047 (5)*
H10	0.693 (3)	0.7102 (11)	0.6426 (14)	0.029 (4)*
H11	0.513 (3)	0.8257 (11)	0.7213 (14)	0.030 (4)*
H1	−0.014 (4)	0.1061 (14)	0.3610 (17)	0.052 (5)*
H2	0.071 (4)	−0.0023 (14)	0.3589 (16)	0.044 (5)*
H3	0.173 (3)	0.1079 (13)	0.5718 (15)	0.039 (4)*
H4	0.402 (3)	0.0711 (11)	0.5297 (15)	0.033 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0245 (4)	0.0243 (4)	0.0172 (4)	0.0054 (3)	0.0067 (3)	0.0014 (3)
O2	0.0231 (4)	0.0265 (5)	0.0249 (5)	0.0029 (3)	0.0056 (3)	−0.0086 (3)
N1	0.0250 (5)	0.0264 (5)	0.0184 (5)	0.0079 (4)	0.0066 (4)	0.0017 (4)
C1	0.0186 (5)	0.0185 (5)	0.0189 (5)	−0.0008 (4)	0.0071 (4)	0.0014 (4)
C2	0.0201 (5)	0.0179 (5)	0.0187 (5)	0.0002 (4)	0.0078 (4)	0.0010 (4)
C3	0.0180 (5)	0.0255 (6)	0.0197 (5)	0.0020 (4)	0.0035 (4)	0.0002 (4)
C4	0.0207 (5)	0.0242 (6)	0.0182 (5)	−0.0010 (4)	0.0041 (4)	−0.0030 (4)
C5	0.0209 (5)	0.0181 (5)	0.0207 (5)	−0.0009 (4)	0.0085 (4)	−0.0016 (4)
C6	0.0171 (5)	0.0253 (6)	0.0234 (6)	0.0017 (4)	0.0035 (4)	−0.0037 (4)
C7	0.0198 (5)	0.0236 (6)	0.0195 (5)	−0.0004 (4)	0.0038 (4)	−0.0040 (4)
O3	0.0234 (5)	0.0407 (6)	0.0269 (5)	0.0015 (4)	0.0033 (4)	0.0110 (4)
C8	0.0300 (7)	0.0439 (8)	0.0309 (7)	−0.0002 (6)	0.0103 (5)	0.0147 (6)
C9	0.0267 (6)	0.0254 (6)	0.0347 (7)	−0.0032 (5)	0.0106 (5)	−0.0012 (5)

Geometric parameters (Å, º) top

O1—C1	1.2498 (14)	C4—C5	1.3923 (17)
O2—C5	1.3543 (15)	C5—C6	1.3965 (16)
O2—H9	0.909 (19)	C6—C7	1.3814 (17)
O3—C9	1.4309 (17)	C3—H11	0.951 (17)
O3—C8ⁱ	1.434 (2)	C4—H10	0.980 (16)
N1—C1	1.3284 (16)	C6—H8	0.962 (17)
N1—H5	0.893 (18)	C7—H7	0.961 (17)
N1—H6	0.895 (19)	C8—C9	1.498 (2)
C1—C2	1.4864 (16)	C8—H1	0.96 (2)
C2—C7	1.3973 (17)	C8—H2	1.04 (2)
C2—C3	1.3924 (16)	C9—H3	0.971 (18)
C3—C4	1.3854 (17)	C9—H4	0.993 (18)

O1···C5ⁱⁱ	3.3571 (17)	C9···H4^xiv	3.060 (17)
O1···N1ⁱⁱⁱ	2.9349 (16)	C9···H6^vi	3.033 (19)
O1···C1^iv	3.2567 (17)	H1···C3^xii	2.98 (2)
O1···O2ⁱⁱ	2.6808 (14)	H1···C4^xii	2.86 (2)
O1···C4ⁱⁱ	3.2448 (17)	H2···H3ⁱ	2.38 (3)
O2···O1^v	2.6808 (14)	H2···O2^xv	2.69 (2)
O3···O3ⁱ	2.8184 (16)	H3···H2ⁱ	2.38 (3)
O3···N1^vi	2.9171 (16)	H3···C5^xvi	2.964 (18)
O1···H7	2.632 (17)	H4···C9^xiv	3.060 (17)
O1···H5ⁱⁱⁱ	2.050 (18)	H4···H8^xvii	2.54 (2)
O1···H10ⁱⁱ	2.544 (16)	H4···H4^xiv	2.55 (2)
O1···H9ⁱⁱ	1.78 (2)	H5···C1ⁱⁱⁱ	2.868 (17)
O2···H2^vii	2.69 (2)	H5···H5ⁱⁱⁱ	2.51 (2)
O2···H7^v	2.806 (17)	H5···O1ⁱⁱⁱ	2.050 (18)
O3···H11^vi	2.721 (16)	H6···C3	2.64 (2)
O3···H6^vi	2.057 (19)	H6···C9^ix	3.033 (19)
N1···C8^viii	3.353 (2)	H6···H11	2.23 (2)
N1···O3^ix	2.9171 (16)	H6···C8^viii	2.70 (2)
N1···O1ⁱⁱⁱ	2.9349 (16)	H6···O3^ix	2.057 (19)
N1···H11	2.668 (16)	H7···O1	2.632 (17)
C1···O1^iv	3.2567 (17)	H7···O2ⁱⁱ	2.806 (17)
C1···C1^iv	3.5941 (19)	H7···H10^xviii	2.58 (2)
C1···C6^x	3.5589 (19)	H7···H9ⁱⁱ	2.38 (3)
C3···C6^x	3.5503 (19)	H8···H4^xix	2.54 (2)
C4···O1^v	3.2448 (17)	H8···H10^xviii	2.51 (2)
C5···O1^v	3.3571 (17)	H9···O1^v	1.78 (2)
C6···C1^xi	3.5589 (19)	H9···H10	2.27 (3)
C6···C3^xi	3.5503 (19)	H9···H7^v	2.38 (3)
C8···N1^viii	3.353 (2)	H9···C1^v	2.813 (19)
C1···H5ⁱⁱⁱ	2.868 (17)	H9···C7^v	3.02 (2)
C1···H9ⁱⁱ	2.813 (19)	H10···H7^xx	2.58 (2)
C3···H1^xii	2.98 (2)	H10···H8^xx	2.51 (2)
C3···H6	2.64 (2)	H10···H9	2.27 (3)
C4···H1^xii	2.86 (2)	H10···O1^v	2.544 (16)
C5···H3^xiii	2.964 (18)	H11···H6	2.23 (2)
C7···H9ⁱⁱ	3.02 (2)	H11···O3^ix	2.721 (16)
C8···H6^viii	2.70 (2)	H11···N1	2.668 (16)

C5—O2—H9	108.3 (14)	C4—C3—H11	118.0 (10)
C8ⁱ—O3—C9	109.51 (11)	C5—C4—H10	120.1 (10)
H5—N1—H6	120.9 (17)	C3—C4—H10	119.9 (10)
C1—N1—H5	117.6 (11)	C5—C6—H8	118.4 (9)
C1—N1—H6	121.3 (14)	C7—C6—H8	121.5 (9)
N1—C1—C2	118.11 (10)	C2—C7—H7	119.0 (10)
O1—C1—N1	120.89 (10)	C6—C7—H7	120.2 (10)
O1—C1—C2	120.98 (10)	O3ⁱ—C8—C9	110.84 (12)
C1—C2—C7	119.81 (10)	O3—C9—C8	109.64 (12)
C3—C2—C7	118.63 (10)	C9—C8—H1	109.7 (12)
C1—C2—C3	121.43 (10)	C9—C8—H2	108.8 (11)
C2—C3—C4	120.93 (11)	H1—C8—H2	110.7 (16)
C3—C4—C5	120.04 (10)	O3ⁱ—C8—H1	106.6 (14)
O2—C5—C4	122.57 (10)	O3ⁱ—C8—H2	110.1 (12)
C4—C5—C6	119.44 (11)	O3—C9—H3	108.6 (10)
O2—C5—C6	118.00 (10)	O3—C9—H4	105.4 (9)
C5—C6—C7	120.13 (11)	C8—C9—H3	111.0 (10)
C2—C7—C6	120.80 (10)	C8—C9—H4	112.6 (10)
C2—C3—H11	121.1 (10)	H3—C9—H4	109.4 (14)

C9—O3—C8ⁱ—C9ⁱ	58.92 (14)	C3—C2—C7—C6	1.44 (17)
C8ⁱ—O3—C9—C8	−58.20 (15)	C2—C3—C4—C5	−0.65 (18)
N1—C1—C2—C3	−30.42 (16)	C3—C4—C5—C6	0.29 (17)
N1—C1—C2—C7	153.69 (11)	C3—C4—C5—O2	180.00 (13)
O1—C1—C2—C7	−27.88 (16)	O2—C5—C6—C7	−178.77 (11)
O1—C1—C2—C3	148.02 (11)	C4—C5—C6—C7	0.93 (17)
C1—C2—C7—C6	177.45 (10)	C5—C6—C7—C2	−1.81 (18)
C1—C2—C3—C4	−176.15 (11)	O3ⁱ—C8—C9—O3	58.99 (16)
C7—C2—C3—C4	−0.21 (17)

Symmetry codes: (i) −x, −y, −z+1; (ii) x, −y+3/2, z+1/2; (iii) −x+1, −y+2, −z+2; (iv) −x+2, −y+2, −z+2; (v) x, −y+3/2, z−1/2; (vi) x, y−1, z; (vii) x+1, −y+1/2, z+1/2; (viii) −x, −y+1, −z+1; (ix) x, y+1, z; (x) x−1, y, z; (xi) x+1, y, z; (xii) −x+1, −y+1, −z+1; (xiii) −x+1, y+1/2, −z+3/2; (xiv) −x+1, −y, −z+1; (xv) x−1, −y+1/2, z−1/2; (xvi) −x+1, y−1/2, −z+3/2; (xvii) −x+2, y−1/2, −z+3/2; (xviii) x+1, −y+3/2, z+1/2; (xix) −x+2, y+1/2, −z+3/2; (xx) x−1, −y+3/2, z−1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H5···O1ⁱⁱⁱ	0.893 (18)	2.050 (18)	2.9349 (16)	170.8 (16)
N1—H6···O3^ix	0.895 (19)	2.057 (19)	2.9171 (16)	161 (2)
O2—H9···O1^v	0.909 (19)	1.78 (2)	2.6808 (14)	173 (2)

Symmetry codes: (iii) −x+1, −y+2, −z+2; (v) x, −y+3/2, z−1/2; (ix) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₇H₇NO₂·0.5C₄H₈O₂
M_r	181.19
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	5.4062 (15), 14.530 (3), 12.027 (2)
β (°)	113.117 (10)
V (Å³)	868.9 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.30 × 0.30 × 0.20

Data collection
Diffractometer	Rigaku Mercury375R (2x2 bin mode) diffractometer
Absorption correction	Multi-scan (REQAB; Jacobson, 1998)
T_min, T_max	0.969, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	9077, 1987, 1841
R_int	0.064
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.111, 1.01
No. of reflections	1987
No. of parameters	162
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.22

Computer programs: CrystalClear-SM Expert (Rigaku, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1999), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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)

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

Acknowledgements

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.

References

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