Isonicotinonitrile-4-methyl-benzoic acid (1/1).

The title structure, C(6)H(4)N(2)·C(8)H(8)O(2), is built up from an assembly of isonicotinonitrile and 4-methyl-benzoic acid mol-ecules and may be regarded as a co-crystal. The two planar mol-ecules [r.m.s. deviations of 0.002 (6) and 0.0028 (11) Å, respectively] are linked by O-H⋯N and C-H⋯O hydrogen bonds. They are nearly coplanar and only twisted from each other by a dihedral angle of 2.48 (6)°. In the crystal, the components are inter-connected by slipped π-π stacking [centroid-centroid distance = 3.6797 (11), slippage = 1.304 Å] and inter-molecular C-H⋯N inter-actions.

Related literature

For the structures of related derivatives, see: Fu et al. (2009 ▶); Aminabhavi et al. (1986 ▶); Dai & Fu (2008a ▶,b ▶). For the graph-set theory, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C6H4N2·C8H8O2

M = 240.26

Monoclinic,

a = 7.5368 (15) Å

b = 13.049 (3) Å

c = 24.749 (5) Å

β = 94.20 (3)°

V = 2427.5 (8) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.40 × 0.30 × 0.20 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.89, T max = 1.00

11659 measured reflections

2752 independent reflections

2416 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.124

S = 1.09

2752 reflections

165 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.18 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶) and ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811019799/dn2689sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811019799/dn2689Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811019799/dn2689Isup3.cml

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

C6H4N2·C8H8O2	F(000) = 1008
Mr = 240.26	Dx = 1.315 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3221 reflections
a = 7.5368 (15) Å	θ = 3.1–27.5°
b = 13.049 (3) Å	µ = 0.09 mm−1
c = 24.749 (5) Å	T = 298 K
β = 94.20 (3)°	Block, colourless
V = 2427.5 (8) Å3	0.40 × 0.30 × 0.20 mm
Z = 8

Rigaku Mercury2 diffractometer	2752 independent reflections
Radiation source: fine-focus sealed tube	2416 reflections with I > 2σ(I)
graphite	Rint = 0.033
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 1.7°
profile data from φ scans	h = −9→9
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −16→16
Tmin = 0.89, Tmax = 1.00	l = −32→32
11659 measured reflections

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0713P)2 + 0.8361P] where P = (Fo2 + 2Fc2)/3
2752 reflections	(Δ/σ)max = 0.001
165 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

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.

	x	y	z	Uiso*/Ueq
N1	0.43937 (13)	0.09948 (8)	0.42051 (4)	0.0221 (2)
N2	−0.17678 (14)	0.10802 (9)	0.29801 (4)	0.0277 (3)
C1	0.28921 (16)	0.13083 (9)	0.44087 (5)	0.0230 (3)
H1A	0.2943	0.1523	0.4768	0.028*
C2	0.12616 (16)	0.13288 (9)	0.41101 (5)	0.0234 (3)
H2A	0.0238	0.1547	0.4264	0.028*
C3	0.12108 (15)	0.10120 (8)	0.35729 (5)	0.0197 (3)
C4	0.27629 (16)	0.06891 (10)	0.33537 (5)	0.0246 (3)
H4A	0.2754	0.0473	0.2995	0.030*
C5	0.43222 (16)	0.06995 (10)	0.36861 (5)	0.0256 (3)
H5A	0.5369	0.0491	0.3542	0.031*
C6	−0.04509 (16)	0.10367 (9)	0.32417 (5)	0.0224 (3)
O1	0.73800 (11)	0.10321 (7)	0.48667 (3)	0.0269 (2)
H1	0.6481	0.1058	0.4659	0.040*
O2	0.55361 (11)	0.16298 (7)	0.54594 (4)	0.0289 (2)
C7	1.30335 (18)	0.15462 (10)	0.69515 (5)	0.0299 (3)
H7A	1.4122	0.1618	0.6776	0.045*
H7B	1.3066	0.0923	0.7158	0.045*
H7C	1.2898	0.2118	0.7189	0.045*
C8	1.14836 (17)	0.15140 (9)	0.65291 (5)	0.0234 (3)
C9	1.16972 (16)	0.11425 (9)	0.60095 (5)	0.0244 (3)
H9A	1.2815	0.0926	0.5920	0.029*
C10	1.02690 (16)	0.10904 (9)	0.56240 (5)	0.0227 (3)
H10A	1.0432	0.0835	0.5280	0.027*
C11	0.85908 (15)	0.14193 (8)	0.57500 (5)	0.0195 (3)
C12	0.83696 (17)	0.17952 (9)	0.62657 (5)	0.0248 (3)
H12A	0.7254	0.2016	0.6354	0.030*
C13	0.98023 (18)	0.18425 (10)	0.66492 (5)	0.0272 (3)
H13A	0.9636	0.2098	0.6993	0.033*
C14	0.70140 (15)	0.13749 (9)	0.53480 (5)	0.0203 (3)

	U11	U22	U33	U12	U13	U23
N1	0.0212 (5)	0.0233 (5)	0.0215 (5)	−0.0027 (4)	0.0000 (4)	0.0016 (4)
N2	0.0229 (5)	0.0348 (6)	0.0251 (5)	0.0010 (4)	−0.0008 (4)	−0.0017 (4)
C1	0.0243 (6)	0.0241 (6)	0.0205 (5)	−0.0011 (4)	0.0001 (4)	−0.0021 (4)
C2	0.0216 (6)	0.0256 (6)	0.0229 (6)	0.0004 (4)	0.0010 (4)	−0.0021 (4)
C3	0.0201 (6)	0.0174 (5)	0.0212 (6)	−0.0025 (4)	−0.0009 (4)	0.0014 (4)
C4	0.0252 (6)	0.0292 (6)	0.0194 (5)	0.0010 (5)	0.0008 (4)	−0.0019 (4)
C5	0.0205 (6)	0.0330 (7)	0.0234 (6)	0.0017 (5)	0.0027 (4)	0.0007 (5)
C6	0.0233 (6)	0.0231 (6)	0.0210 (5)	−0.0005 (4)	0.0020 (5)	−0.0015 (4)
O1	0.0188 (4)	0.0422 (5)	0.0194 (4)	0.0009 (4)	−0.0011 (3)	−0.0046 (4)
O2	0.0200 (5)	0.0370 (5)	0.0295 (5)	0.0029 (4)	0.0000 (3)	−0.0074 (4)
C7	0.0301 (7)	0.0302 (7)	0.0279 (6)	−0.0046 (5)	−0.0085 (5)	0.0007 (5)
C8	0.0263 (6)	0.0208 (6)	0.0223 (6)	−0.0048 (4)	−0.0037 (5)	0.0030 (4)
C9	0.0196 (6)	0.0288 (6)	0.0249 (6)	−0.0008 (4)	0.0015 (4)	0.0019 (5)
C10	0.0217 (6)	0.0275 (6)	0.0189 (5)	−0.0023 (5)	0.0019 (4)	−0.0001 (4)
C11	0.0208 (6)	0.0177 (5)	0.0198 (5)	−0.0027 (4)	0.0009 (4)	0.0010 (4)
C12	0.0234 (6)	0.0259 (6)	0.0253 (6)	0.0006 (5)	0.0024 (5)	−0.0032 (5)
C13	0.0320 (7)	0.0289 (6)	0.0205 (5)	−0.0012 (5)	−0.0002 (5)	−0.0044 (5)
C14	0.0205 (6)	0.0186 (5)	0.0220 (6)	−0.0024 (4)	0.0018 (4)	0.0003 (4)

N1—C1	1.3362 (16)	C7—C8	1.5100 (17)
N1—C5	1.3384 (16)	C7—H7A	0.9600
N2—C6	1.1461 (16)	C7—H7B	0.9600
C1—C2	1.3871 (17)	C7—H7C	0.9600
C1—H1A	0.9300	C8—C13	1.3903 (18)
C2—C3	1.3903 (16)	C8—C9	1.3946 (17)
C2—H2A	0.9300	C9—C10	1.3866 (17)
C3—C4	1.3903 (17)	C9—H9A	0.9300
C3—C6	1.4459 (17)	C10—C11	1.3925 (17)
C4—C5	1.3844 (17)	C10—H10A	0.9300
C4—H4A	0.9300	C11—C12	1.3886 (16)
C5—H5A	0.9300	C11—C14	1.4942 (16)
O1—C14	1.3202 (14)	C12—C13	1.3858 (18)
O1—H1	0.8200	C12—H12A	0.9300
O2—C14	1.2134 (15)	C13—H13A	0.9300
C1—N1—C5	118.32 (10)	H7B—C7—H7C	109.5
N1—C1—C2	123.14 (11)	C13—C8—C9	118.23 (11)
N1—C1—H1A	118.4	C13—C8—C7	120.95 (11)
C2—C1—H1A	118.4	C9—C8—C7	120.82 (11)
C1—C2—C3	117.72 (11)	C10—C9—C8	121.01 (11)
C1—C2—H2A	121.1	C10—C9—H9A	119.5
C3—C2—H2A	121.1	C8—C9—H9A	119.5
C4—C3—C2	119.88 (11)	C9—C10—C11	120.19 (11)
C4—C3—C6	120.28 (10)	C9—C10—H10A	119.9
C2—C3—C6	119.83 (11)	C11—C10—H10A	119.9
C5—C4—C3	117.85 (11)	C12—C11—C10	119.13 (11)
C5—C4—H4A	121.1	C12—C11—C14	118.85 (11)
C3—C4—H4A	121.1	C10—C11—C14	122.01 (10)
N1—C5—C4	123.09 (11)	C13—C12—C11	120.35 (11)
N1—C5—H5A	118.5	C13—C12—H12A	119.8
C4—C5—H5A	118.5	C11—C12—H12A	119.8
N2—C6—C3	178.44 (13)	C12—C13—C8	121.09 (11)
C14—O1—H1	109.5	C12—C13—H13A	119.5
C8—C7—H7A	109.5	C8—C13—H13A	119.5
C8—C7—H7B	109.5	O2—C14—O1	123.63 (11)
H7A—C7—H7B	109.5	O2—C14—C11	122.45 (10)
C8—C7—H7C	109.5	O1—C14—C11	113.91 (10)
H7A—C7—H7C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.87	2.6850 (15)	175
C1—H1A···O2	0.93	2.51	3.1858 (18)	130
C4—H4A···N2i	0.93	2.60	3.3700 (18)	141

CgI	CgJ	CgI···CgJa	CgI···P(J)b	CgJ···P(I)c	Slippage
Cg1	Cg2ii	3.6797 (11)	3.440	3.443	1.304

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.87	2.6850 (15)	175
C1—H1A⋯O2	0.93	2.51	3.1858 (18)	130
C4—H4A⋯N2i	0.93	2.60	3.3700 (18)	141

Symmetry code: (i) .