4-Acetyl-pyridine-fumaric acid (2/1).

In the crystal structure of the title cocrystal, 2C(7)H(7)NO·C(4)H(4)O(4), the complete fumaric acid mol-ecule is generated by a crystallographic inversion centre. The two components of the cocrystal are linked by an O-H⋯N hydrogen bond.

Related literature

For biological and medicinal applications of 4-acetyl­pyridine and fumaric acid, see: Fidler et al. (2003 ▶); Thomas et al. (2007 ▶). For mol­ecular complexes of neutral pyridine derivatives and neutral fumaric acid, see: Bowes et al. (2003 ▶); Aakeroy et al. (2002 ▶, 2006 ▶, 2007 ▶); Haynes et al. (2006 ▶); Bu et al. (2007 ▶). For literature on C—O bond distances in fumaric acid, see: Liu et al. (2003 ▶). For metal complexes of 4-acetyl­pyridine, see: Steffen & Palenik (1977 ▶); Pang et al. (1994 ▶). For a 4-acetyl­pyridinium salt, see: Kochel (2005 ▶).

Experimental

Crystal data

2C7H7NO·C4H4O4

M = 358.34

Triclinic,

a = 3.9062 (5) Å

b = 8.6809 (13) Å

c = 13.0909 (18) Å

α = 87.925 (4)°

β = 89.941 (3)°

γ = 83.141 (4)°

V = 440.44 (11) Å3

Z = 1

Mo Kα radiation

μ = 0.10 mm−1

T = 294 K

0.30 × 0.11 × 0.08 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer

Absorption correction: none

3600 measured reflections

1589 independent reflections

798 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.143

S = 1.18

1589 reflections

124 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.20 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809020480/ng2588sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809020480/ng2588Isup2.hkl

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

2C7H7NO·C4H4O4	Z = 1
Mr = 358.34	F(000) = 188
Triclinic, P1	Dx = 1.351 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 3.9062 (5) Å	Cell parameters from 2308 reflections
b = 8.6809 (13) Å	θ = 3.2–24.6°
c = 13.0909 (18) Å	µ = 0.10 mm−1
α = 87.925 (4)°	T = 294 K
β = 89.941 (3)°	Needle, colourless
γ = 83.141 (4)°	0.30 × 0.11 × 0.08 mm
V = 440.44 (11) Å3

Rigaku R-AXIS RAPID IP diffractometer	798 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.030
graphite	θmax = 25.2°, θmin = 3.1°
ω scans	h = −4→4
3600 measured reflections	k = −10→10
1589 independent reflections	l = −15→15

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.143	w = 1/[σ2(Fo2) + (0.0527P)2 + 0.048P] where P = (Fo2 + 2Fc2)/3
S = 1.18	(Δ/σ)max = 0.001
1589 reflections	Δρmax = 0.19 e Å−3
124 parameters	Δρmin = −0.20 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.032 (8)

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.

	x	y	z	Uiso*/Ueq
N1	0.4491 (6)	0.4588 (3)	0.69775 (18)	0.0630 (7)
O1	0.8832 (6)	0.7499 (3)	0.98158 (16)	0.0900 (8)
O2	0.1660 (6)	0.1037 (2)	0.67034 (15)	0.0775 (7)
O3	0.2584 (6)	0.2870 (3)	0.55473 (16)	0.0764 (7)
C1	0.5832 (8)	0.4178 (4)	0.7899 (2)	0.0733 (9)
H1	0.6122	0.3130	0.8097	0.088*
C2	0.6807 (7)	0.5230 (3)	0.8573 (2)	0.0651 (9)
H2	0.7765	0.4894	0.9204	0.078*
C3	0.6342 (6)	0.6786 (3)	0.82954 (19)	0.0494 (7)
C4	0.4891 (6)	0.7228 (3)	0.73526 (19)	0.0546 (7)
H4	0.4508	0.8270	0.7145	0.065*
C5	0.4019 (7)	0.6088 (4)	0.6724 (2)	0.0612 (8)
H5	0.3048	0.6391	0.6089	0.073*
C6	0.7453 (7)	0.7954 (3)	0.9018 (2)	0.0562 (8)
C7	0.6902 (7)	0.9624 (3)	0.8712 (2)	0.0653 (9)
H7A	0.7914	1.0212	0.9215	0.098*
H7B	0.4474	0.9961	0.8664	0.098*
H7C	0.7961	0.9784	0.8061	0.098*
C8	0.1658 (7)	0.1535 (3)	0.5833 (2)	0.0539 (7)
C9	0.0643 (7)	0.0651 (3)	0.4951 (2)	0.0561 (8)
H9	0.0951	0.1057	0.4295	0.067*
H3A	0.335 (9)	0.337 (5)	0.615 (3)	0.131 (14)*

	U11	U22	U33	U12	U13	U23
N1	0.0771 (16)	0.0500 (17)	0.0641 (16)	−0.0142 (12)	−0.0009 (13)	−0.0083 (13)
O1	0.1244 (18)	0.0731 (17)	0.0703 (14)	−0.0004 (13)	−0.0407 (14)	−0.0077 (12)
O2	0.1167 (18)	0.0640 (15)	0.0548 (13)	−0.0234 (12)	−0.0138 (12)	0.0004 (11)
O3	0.1198 (18)	0.0541 (15)	0.0607 (13)	−0.0313 (13)	−0.0048 (12)	−0.0076 (11)
C1	0.096 (2)	0.046 (2)	0.077 (2)	−0.0096 (17)	−0.0064 (19)	0.0019 (17)
C2	0.082 (2)	0.052 (2)	0.0610 (19)	−0.0053 (15)	−0.0123 (16)	0.0030 (15)
C3	0.0523 (15)	0.0448 (18)	0.0513 (16)	−0.0058 (12)	−0.0004 (13)	−0.0030 (13)
C4	0.0682 (17)	0.0451 (17)	0.0512 (16)	−0.0100 (13)	−0.0046 (14)	−0.0014 (13)
C5	0.0704 (18)	0.057 (2)	0.0566 (18)	−0.0100 (15)	−0.0086 (15)	−0.0024 (15)
C6	0.0577 (16)	0.057 (2)	0.0541 (18)	−0.0048 (13)	−0.0047 (14)	−0.0051 (14)
C7	0.0738 (19)	0.054 (2)	0.070 (2)	−0.0163 (15)	−0.0083 (16)	−0.0077 (16)
C8	0.0604 (16)	0.0446 (18)	0.0567 (18)	−0.0048 (13)	−0.0084 (14)	−0.0063 (14)
C9	0.0680 (17)	0.0469 (18)	0.0534 (16)	−0.0063 (13)	−0.0072 (14)	−0.0016 (14)

N1—C5	1.323 (4)	C3—C6	1.512 (4)
N1—C1	1.335 (4)	C4—C5	1.383 (4)
O1—C6	1.207 (3)	C4—H4	0.9300
O2—C8	1.204 (3)	C5—H5	0.9300
O3—C8	1.297 (3)	C6—C7	1.481 (4)
O3—H3A	0.97 (4)	C7—H7A	0.9600
C1—C2	1.378 (4)	C7—H7B	0.9600
C1—H1	0.9300	C7—H7C	0.9600
C2—C3	1.377 (4)	C8—C9	1.488 (4)
C2—H2	0.9300	C9—C9i	1.293 (5)
C3—C4	1.381 (3)	C9—H9	0.9300
C5—N1—C1	117.3 (3)	C4—C5—H5	118.2
C8—O3—H3A	108 (2)	O1—C6—C7	121.8 (3)
N1—C1—C2	123.2 (3)	O1—C6—C3	119.3 (3)
N1—C1—H1	118.4	C7—C6—C3	118.9 (2)
C2—C1—H1	118.4	C6—C7—H7A	109.5
C3—C2—C1	118.9 (3)	C6—C7—H7B	109.5
C3—C2—H2	120.5	H7A—C7—H7B	109.5
C1—C2—H2	120.5	C6—C7—H7C	109.5
C2—C3—C4	118.4 (2)	H7A—C7—H7C	109.5
C2—C3—C6	119.6 (2)	H7B—C7—H7C	109.5
C4—C3—C6	122.0 (3)	O2—C8—O3	124.8 (3)
C3—C4—C5	118.6 (3)	O2—C8—C9	123.1 (3)
C3—C4—H4	120.7	O3—C8—C9	112.2 (3)
C5—C4—H4	120.7	C9i—C9—C8	123.6 (3)
N1—C5—C4	123.5 (3)	C9i—C9—H9	118.2
N1—C5—H5	118.2	C8—C9—H9	118.2

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···N1	0.98 (4)	1.64 (4)	2.599 (3)	166 (4)
C4—H4···O2ii	0.93	2.57	3.471 (3)	164
C7—H7C···O2iii	0.96	2.58	3.489 (3)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯N1	0.98 (4)	1.64 (4)	2.599 (3)	166 (4)