Isonicotinamide-2-naphthoic acid (1/1).

In the title 1:1 adduct, C(6)H(6)N(2)O·C(11)H(8)O(2), the amide group is slightly twisted out of the plane of the aromatic ring, with a C-C-C-N torsion angle of 25.11 (19)°, whereas the carb-oxy-lic acid group is approximately coplanar with the bicylic ring system, with a C-C-C-O torsion angle of 10.9 (2)°. The amide groups from two isonicotinamide mol-ecules form a dimer via N-H⋯O hydrogen bonds. In addition, the 2-naphthanoic acid mol-ecule is hydrogen bonded to the pyridine unit of an isonicotinamide mol-ecule via an O-H⋯N hydrogen bond. This gives rise to a centrosymmetric four-mol-ecule chain, which is cross-linked by further N-H⋯O hydrogen bonds from the amide group.

Related literature

For related compounds, see: Lemmerer et al. (2008 ▶); Aakeröy et al. (2002 ▶); Báthori et al. (2010 ▶). The carb­oxy­lic acid–pyridine hydrogen bond is an often used supra­molecular synthon, see: Aakeröy & Beatty (2001 ▶).

Experimental

Crystal data

C6H6N2O·C11H8O2

M = 294.3

Monoclinic,

a = 8.6665 (17) Å

b = 23.752 (5) Å

c = 7.3793 (15) Å

β = 110.33 (3)°

V = 1424.4 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 173 K

0.48 × 0.45 × 0.08 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: integration (XPREP; Bruker, 2007 ▶) T min = 0.956, T max = 0.993

7507 measured reflections

2605 independent reflections

2130 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.119

S = 1.01

2605 reflections

211 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT-Plus (Bruker, 2007 ▶); data reduction: SAINT-Plus and XPREP (Bruker, 2007 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811050057/fj2462sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811050057/fj2462Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811050057/fj2462Isup3.mol

Supplementary material file. DOI: 10.1107/S1600536811050057/fj2462Isup4.cml

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

C6H6N2O·C11H8O2	F(000) = 616
Mr = 294.3	Dx = 1.372 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5555 reflections
a = 8.6665 (17) Å	θ = 1–27.5°
b = 23.752 (5) Å	µ = 0.10 mm−1
c = 7.3793 (15) Å	T = 173 K
β = 110.33 (3)°	Block, colourless
V = 1424.4 (5) Å3	0.48 × 0.45 × 0.08 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	2130 reflections with I > 2σ(I)
ω scans	Rint = 0.055
Absorption correction: integration (XPREP; Bruker, 2007)	θmax = 25.5°, θmin = 3.0°
Tmin = 0.956, Tmax = 0.993	h = −10→10
7507 measured reflections	k = −28→27
2605 independent reflections	l = −8→7

Refinement on F2	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.041	w = 1/[σ2(Fo2) + (0.0731P)2 + 0.1531P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.119	(Δ/σ)max < 0.001
S = 1.01	Δρmax = 0.21 e Å−3
2605 reflections	Δρmin = −0.20 e Å−3
211 parameters

Experimental. Numerical integration absorption corrections based on indexed crystal faces were applied using the XPREP routine (Bruker, 2004)

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.

	x	y	z	Uiso*/Ueq
C1	1.10423 (17)	0.44738 (6)	0.71685 (18)	0.0248 (3)
C2	1.08405 (18)	0.40155 (6)	0.59333 (19)	0.0281 (3)
H2A	1.1769	0.3829	0.5809	0.034*
C3	0.92709 (18)	0.38371 (7)	0.48958 (19)	0.0325 (4)
H3	0.9143	0.3518	0.4079	0.039*
C4	0.81087 (18)	0.45238 (7)	0.6185 (2)	0.0329 (4)
H4	0.7157	0.4703	0.627	0.039*
C5	0.96357 (17)	0.47215 (6)	0.7311 (2)	0.0292 (3)
H5	0.9727	0.5025	0.8179	0.035*
C6	1.26979 (17)	0.47009 (6)	0.83740 (19)	0.0271 (3)
N1	1.39399 (17)	0.46082 (6)	0.77495 (19)	0.0324 (3)
H1S	1.496 (2)	0.4727 (7)	0.846 (2)	0.036 (4)*
H1A	1.375 (2)	0.4460 (8)	0.663 (3)	0.042 (5)*
N2	0.79178 (15)	0.40878 (6)	0.49762 (16)	0.0335 (3)
O1	1.28451 (13)	0.49617 (5)	0.98726 (14)	0.0371 (3)
C7	0.23811 (17)	0.35294 (6)	0.12753 (18)	0.0257 (3)
C8	0.25613 (18)	0.30807 (6)	0.00900 (19)	0.0301 (3)
H8	0.363	0.2962	0.0172	0.036*
C9	0.12123 (18)	0.28196 (6)	−0.11624 (19)	0.0313 (4)
H9	0.1354	0.2517	−0.1931	0.038*
C10	−0.03974 (17)	0.29913 (6)	−0.13394 (19)	0.0267 (3)
C11	−0.18280 (19)	0.27324 (7)	−0.2630 (2)	0.0350 (4)
H11	−0.1722	0.2426	−0.3407	0.042*
C12	−0.33562 (19)	0.29162 (7)	−0.2774 (2)	0.0382 (4)
H12	−0.4301	0.2737	−0.3652	0.046*
C13	−0.35493 (19)	0.33669 (7)	−0.1639 (2)	0.0355 (4)
H13	−0.4621	0.3489	−0.1745	0.043*
C14	−0.21997 (17)	0.36309 (6)	−0.0382 (2)	0.0289 (3)
H14	−0.2341	0.3938	0.0371	0.035*
C15	−0.05903 (16)	0.34512 (6)	−0.01926 (18)	0.0243 (3)
C16	0.08343 (17)	0.37060 (6)	0.11132 (18)	0.0246 (3)
H16	0.0717	0.4008	0.19	0.03*
C17	0.38436 (18)	0.38080 (6)	0.2707 (2)	0.0302 (3)
O2	0.52342 (13)	0.36681 (6)	0.25195 (16)	0.0444 (3)
H2	0.624 (3)	0.3858 (10)	0.359 (3)	0.085 (7)*
O3	0.37325 (13)	0.41309 (5)	0.39438 (14)	0.0404 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0286 (8)	0.0233 (7)	0.0214 (6)	−0.0021 (6)	0.0072 (6)	0.0041 (5)
C2	0.0270 (8)	0.0301 (8)	0.0269 (7)	−0.0037 (6)	0.0091 (6)	−0.0028 (6)
C3	0.0341 (9)	0.0365 (9)	0.0271 (7)	−0.0082 (7)	0.0109 (6)	−0.0049 (6)
C4	0.0282 (8)	0.0393 (9)	0.0319 (8)	0.0055 (7)	0.0112 (6)	0.0092 (7)
C5	0.0339 (8)	0.0251 (8)	0.0288 (7)	0.0010 (6)	0.0112 (6)	0.0022 (6)
C6	0.0298 (8)	0.0236 (8)	0.0252 (7)	−0.0030 (6)	0.0061 (6)	0.0005 (6)
N1	0.0279 (7)	0.0398 (8)	0.0278 (6)	−0.0076 (6)	0.0076 (5)	−0.0106 (6)
N2	0.0276 (7)	0.0444 (9)	0.0267 (6)	−0.0059 (6)	0.0069 (5)	0.0025 (6)
O1	0.0361 (6)	0.0413 (7)	0.0340 (6)	−0.0097 (5)	0.0121 (5)	−0.0167 (5)
C7	0.0271 (8)	0.0270 (8)	0.0230 (6)	−0.0014 (6)	0.0087 (6)	0.0021 (6)
C8	0.0286 (8)	0.0304 (8)	0.0317 (7)	0.0044 (6)	0.0112 (6)	−0.0011 (6)
C9	0.0379 (9)	0.0264 (8)	0.0305 (7)	0.0026 (6)	0.0130 (7)	−0.0056 (6)
C10	0.0327 (8)	0.0213 (7)	0.0258 (7)	−0.0020 (6)	0.0098 (6)	0.0008 (6)
C11	0.0413 (9)	0.0280 (8)	0.0334 (8)	−0.0074 (7)	0.0099 (7)	−0.0056 (6)
C12	0.0316 (9)	0.0385 (10)	0.0381 (8)	−0.0129 (7)	0.0038 (7)	−0.0021 (7)
C13	0.0259 (8)	0.0379 (9)	0.0411 (8)	0.0003 (7)	0.0098 (6)	0.0079 (7)
C14	0.0301 (8)	0.0261 (8)	0.0312 (7)	0.0021 (6)	0.0115 (6)	0.0036 (6)
C15	0.0281 (8)	0.0207 (7)	0.0244 (6)	−0.0009 (6)	0.0095 (6)	0.0034 (5)
C16	0.0300 (8)	0.0206 (7)	0.0233 (7)	−0.0008 (6)	0.0093 (6)	−0.0006 (5)
C17	0.0295 (8)	0.0356 (9)	0.0249 (7)	−0.0026 (7)	0.0088 (6)	0.0009 (6)
O2	0.0242 (6)	0.0654 (9)	0.0411 (6)	−0.0041 (5)	0.0081 (5)	−0.0160 (6)
O3	0.0369 (7)	0.0517 (8)	0.0316 (6)	−0.0080 (5)	0.0107 (5)	−0.0149 (5)

C1—C5	1.390 (2)	C8—H8	0.95
C1—C2	1.3912 (19)	C9—C10	1.415 (2)
C1—C6	1.501 (2)	C9—H9	0.95
C2—C3	1.376 (2)	C10—C11	1.415 (2)
C2—H2A	0.95	C10—C15	1.4269 (19)
C3—N2	1.335 (2)	C11—C12	1.363 (2)
C3—H3	0.95	C11—H11	0.95
C4—N2	1.339 (2)	C12—C13	1.405 (2)
C4—C5	1.378 (2)	C12—H12	0.95
C4—H4	0.95	C13—C14	1.366 (2)
C5—H5	0.95	C13—H13	0.95
C6—O1	1.2349 (16)	C14—C15	1.4182 (19)
C6—N1	1.3282 (19)	C14—H14	0.95
N1—H1S	0.904 (19)	C15—C16	1.412 (2)
N1—H1A	0.862 (18)	C16—H16	0.95
C7—C16	1.370 (2)	C17—O3	1.2215 (17)
C7—C8	1.421 (2)	C17—O2	1.3029 (18)
C7—C17	1.493 (2)	O2—H2	1.05 (3)
C8—C9	1.362 (2)
C5—C1—C2	117.82 (13)	C8—C9—C10	121.18 (13)
C5—C1—C6	119.06 (13)	C8—C9—H9	119.4
C2—C1—C6	123.10 (13)	C10—C9—H9	119.4
C3—C2—C1	118.72 (14)	C11—C10—C9	122.83 (14)
C3—C2—H2A	120.6	C11—C10—C15	118.43 (13)
C1—C2—H2A	120.6	C9—C10—C15	118.73 (13)
N2—C3—C2	123.51 (14)	C12—C11—C10	120.93 (14)
N2—C3—H3	118.2	C12—C11—H11	119.5
C2—C3—H3	118.2	C10—C11—H11	119.5
N2—C4—C5	122.39 (14)	C11—C12—C13	120.75 (14)
N2—C4—H4	118.8	C11—C12—H12	119.6
C5—C4—H4	118.8	C13—C12—H12	119.6
C4—C5—C1	119.62 (14)	C14—C13—C12	120.20 (14)
C4—C5—H5	120.2	C14—C13—H13	119.9
C1—C5—H5	120.2	C12—C13—H13	119.9
O1—C6—N1	123.36 (14)	C13—C14—C15	120.63 (14)
O1—C6—C1	119.40 (13)	C13—C14—H14	119.7
N1—C6—C1	117.24 (12)	C15—C14—H14	119.7
C6—N1—H1S	119.8 (10)	C16—C15—C14	122.37 (13)
C6—N1—H1A	119.9 (12)	C16—C15—C10	118.57 (12)
H1S—N1—H1A	120.1 (15)	C14—C15—C10	119.06 (13)
C3—N2—C4	117.87 (13)	C7—C16—C15	121.72 (13)
C16—C7—C8	119.30 (13)	C7—C16—H16	119.1
C16—C7—C17	119.37 (13)	C15—C16—H16	119.1
C8—C7—C17	121.32 (13)	O3—C17—O2	123.73 (14)
C9—C8—C7	120.47 (13)	O3—C17—C7	122.62 (13)
C9—C8—H8	119.8	O2—C17—C7	113.65 (13)
C7—C8—H8	119.8	C17—O2—H2	111.5 (13)
C5—C1—C2—C3	1.1 (2)	C15—C10—C11—C12	−0.2 (2)
C6—C1—C2—C3	179.67 (12)	C10—C11—C12—C13	−0.2 (2)
C1—C2—C3—N2	1.5 (2)	C11—C12—C13—C14	0.6 (2)
N2—C4—C5—C1	1.7 (2)	C12—C13—C14—C15	−0.6 (2)
C2—C1—C5—C4	−2.6 (2)	C13—C14—C15—C16	−178.83 (12)
C6—C1—C5—C4	178.77 (12)	C13—C14—C15—C10	0.2 (2)
C5—C1—C6—O1	23.6 (2)	C11—C10—C15—C16	179.24 (12)
C2—C1—C6—O1	−155.01 (14)	C9—C10—C15—C16	−1.78 (19)
C5—C1—C6—N1	−156.32 (13)	C11—C10—C15—C14	0.13 (19)
C2—C1—C6—N1	25.11 (19)	C9—C10—C15—C14	179.11 (12)
C2—C3—N2—C4	−2.4 (2)	C8—C7—C16—C15	0.5 (2)
C5—C4—N2—C3	0.8 (2)	C17—C7—C16—C15	−178.93 (11)
C16—C7—C8—C9	−1.5 (2)	C14—C15—C16—C7	−179.74 (12)
C17—C7—C8—C9	177.85 (13)	C10—C15—C16—C7	1.2 (2)
C7—C8—C9—C10	0.9 (2)	C16—C7—C17—O3	11.1 (2)
C8—C9—C10—C11	179.69 (13)	C8—C7—C17—O3	−168.30 (14)
C8—C9—C10—C15	0.8 (2)	C16—C7—C17—O2	−169.70 (13)
C9—C10—C11—C12	−179.09 (14)	C8—C7—C17—O2	10.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1S···O1i	0.904 (19)	2.012 (19)	2.914 (2)	176 (2)
N1—H1A···O3ii	0.862 (18)	2.123 (18)	2.9755 (17)	170 (2)
O2—H2···N2	1.05 (3)	1.56 (3)	2.5999 (18)	170 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1S⋯O1i	0.904 (19)	2.012 (19)	2.914 (2)	176 (2)
N1—H1A⋯O3ii	0.862 (18)	2.123 (18)	2.9755 (17)	170 (2)
O2—H2⋯N2	1.05 (3)	1.56 (3)	2.5999 (18)	170 (2)

Symmetry codes: (i) ; (ii) .