2,6-Diacetyl-pyridine-resorcinol (1/1).

The title co-crystal, C(9)H(9)NO(2)·C(6)H(6)O(2), is composed of one 2,6-diacetyl-pyridine mol-ecule and one resorcinol mol-ecule as the asymmetric unit. In the 2,6-diacetyl-pyridine mol-ecule, the two carbonyl groups are anti-periplanar to the pyridine N atom. In the crystal, the 2,6-diacetyl-pyridine and resorcinol mol-ecules are connected by two O-H⋯O hydrogen bonds, forming planar chains of alternating components running along [120].

Related literature

For background to 2,6-diacetyl­pyridine and resorcinol, see: Bacon & Lisher (1980 ▶); MacGillivray et al. (2000 ▶); Boldog et al. (2004 ▶); Matsumoto et al. (2006 ▶); Anwar et al. (2007 ▶); Friščić & MacGillivray (2009 ▶).

Experimental

Crystal data

C9H9NO2·C6H6O2

M = 273.28

Triclinic,

a = 7.346 (2) Å

b = 7.866 (2) Å

c = 12.342 (3) Å

α = 101.61 (3)°

β = 90.51 (3)°

γ = 98.72 (3)°

V = 689.9 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 173 K

0.30 × 0.30 × 0.23 mm

Data collection

Stoe IPDS II two-circle diffractometer

9113 measured reflections

2515 independent reflections

1605 reflections with I > 2σ(I)

R int = 0.094

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.130

S = 0.93

2515 reflections

185 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.27 e Å−3

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2001 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812035131/ng5287sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812035131/ng5287Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812035131/ng5287Isup3.cml

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

C9H9NO2·C6H6O2	Z = 2
Mr = 273.28	F(000) = 288
Triclinic, P1	Dx = 1.315 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.346 (2) Å	Cell parameters from 9113 reflections
b = 7.866 (2) Å	θ = 3.8–25.6°
c = 12.342 (3) Å	µ = 0.10 mm−1
α = 101.61 (3)°	T = 173 K
β = 90.51 (3)°	Block, colourless
γ = 98.72 (3)°	0.30 × 0.30 × 0.23 mm
V = 689.9 (3) Å3

Stoe IPDS II two-circle diffractometer	1605 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.094
Graphite monochromator	θmax = 25.4°, θmin = 3.2°
ω scans	h = −8→8
9113 measured reflections	k = −9→9
2515 independent reflections	l = −14→14

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130	H-atom parameters constrained
S = 0.93	w = 1/[σ2(Fo2) + (0.0671P)2] where P = (Fo2 + 2Fc2)/3
2515 reflections	(Δ/σ)max < 0.001
185 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

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	0.2051 (2)	0.1792 (2)	0.23716 (14)	0.0241 (4)
O1	0.0057 (2)	−0.2404 (2)	0.27810 (15)	0.0442 (5)
O2	0.4266 (2)	0.6213 (2)	0.27795 (14)	0.0421 (5)
C1	0.2841 (2)	0.3381 (3)	0.29483 (18)	0.0244 (5)
C2	0.3093 (3)	0.3761 (3)	0.40993 (19)	0.0290 (5)
H2	0.3624	0.4906	0.4478	0.035*
C3	0.2559 (3)	0.2451 (3)	0.46820 (19)	0.0323 (5)
H3	0.2723	0.2674	0.5465	0.039*
C4	0.1779 (3)	0.0805 (3)	0.40953 (19)	0.0304 (5)
H4	0.1426	−0.0131	0.4469	0.036*
C5	0.1518 (2)	0.0537 (3)	0.29475 (18)	0.0243 (5)
C6	0.0608 (3)	−0.1218 (3)	0.22941 (19)	0.0283 (5)
C7	0.0371 (3)	−0.1447 (3)	0.1066 (2)	0.0385 (6)
H7A	0.0046	−0.2700	0.0734	0.058*
H7B	0.1526	−0.0971	0.0767	0.058*
H7C	−0.0614	−0.0821	0.0892	0.058*
C8	0.3460 (3)	0.4780 (3)	0.22922 (19)	0.0277 (5)
C9	0.3053 (3)	0.4348 (3)	0.1071 (2)	0.0371 (6)
H9A	0.3542	0.5361	0.0752	0.056*
H9B	0.1717	0.4063	0.0924	0.056*
H9C	0.3634	0.3336	0.0735	0.056*
O3	0.5190 (2)	0.8749 (2)	0.15119 (15)	0.0440 (5)
HO3	0.4909	0.8049	0.1937	0.066*
O4	0.8147 (2)	1.4495 (2)	0.14755 (14)	0.0437 (5)
HO4	0.8697	1.5413	0.1891	0.066*
C11	0.6121 (3)	1.0305 (3)	0.2107 (2)	0.0292 (5)
C12	0.6507 (3)	1.0573 (3)	0.3241 (2)	0.0335 (6)
H12	0.6119	0.9671	0.3635	0.040*
C13	0.7473 (3)	1.2191 (3)	0.3788 (2)	0.0345 (6)
H13	0.7743	1.2385	0.4561	0.041*
C14	0.8046 (3)	1.3522 (3)	0.3220 (2)	0.0331 (6)
H14	0.8705	1.4616	0.3600	0.040*
C15	0.7642 (3)	1.3232 (3)	0.2090 (2)	0.0301 (5)
C16	0.6671 (3)	1.1633 (3)	0.1528 (2)	0.0331 (5)
H16	0.6386	1.1448	0.0757	0.040*

	U11	U22	U33	U12	U13	U23
N1	0.0187 (8)	0.0236 (10)	0.0286 (10)	−0.0016 (7)	0.0019 (7)	0.0060 (8)
O1	0.0515 (10)	0.0298 (9)	0.0484 (11)	−0.0118 (8)	0.0009 (8)	0.0150 (8)
O2	0.0482 (9)	0.0262 (9)	0.0464 (11)	−0.0139 (7)	−0.0057 (8)	0.0094 (8)
C1	0.0179 (9)	0.0252 (11)	0.0290 (13)	−0.0012 (8)	0.0001 (8)	0.0063 (9)
C2	0.0250 (10)	0.0265 (12)	0.0322 (13)	−0.0015 (9)	−0.0039 (9)	0.0028 (10)
C3	0.0317 (11)	0.0377 (13)	0.0260 (13)	0.0021 (10)	−0.0004 (9)	0.0057 (10)
C4	0.0265 (11)	0.0329 (12)	0.0337 (14)	0.0004 (9)	0.0051 (9)	0.0144 (11)
C5	0.0196 (10)	0.0227 (11)	0.0308 (13)	0.0002 (8)	0.0039 (9)	0.0084 (9)
C6	0.0219 (10)	0.0249 (12)	0.0379 (14)	−0.0007 (8)	0.0021 (9)	0.0092 (10)
C7	0.0447 (13)	0.0281 (12)	0.0378 (15)	−0.0061 (10)	−0.0035 (11)	0.0041 (11)
C8	0.0224 (10)	0.0230 (11)	0.0372 (14)	−0.0009 (8)	0.0005 (9)	0.0083 (10)
C9	0.0431 (13)	0.0334 (13)	0.0348 (14)	−0.0040 (10)	0.0023 (11)	0.0147 (11)
O3	0.0492 (10)	0.0281 (9)	0.0507 (11)	−0.0123 (7)	−0.0084 (8)	0.0123 (8)
O4	0.0503 (10)	0.0290 (9)	0.0481 (11)	−0.0114 (8)	0.0098 (8)	0.0121 (8)
C11	0.0219 (10)	0.0217 (11)	0.0431 (15)	−0.0028 (8)	0.0019 (9)	0.0085 (10)
C12	0.0302 (11)	0.0306 (13)	0.0442 (16)	0.0046 (9)	0.0037 (10)	0.0180 (11)
C13	0.0319 (12)	0.0353 (13)	0.0367 (14)	0.0066 (10)	−0.0023 (10)	0.0077 (11)
C14	0.0267 (11)	0.0250 (12)	0.0454 (16)	0.0010 (9)	−0.0005 (10)	0.0043 (11)
C15	0.0230 (10)	0.0234 (11)	0.0446 (15)	−0.0008 (8)	0.0091 (10)	0.0114 (10)
C16	0.0303 (11)	0.0321 (13)	0.0367 (14)	0.0011 (9)	0.0052 (10)	0.0095 (11)

N1—C5	1.343 (2)	C9—H9A	0.9800
N1—C1	1.349 (3)	C9—H9B	0.9800
O1—C6	1.229 (2)	C9—H9C	0.9800
O2—C8	1.226 (3)	O3—C11	1.371 (3)
C1—C2	1.396 (3)	O3—HO3	0.8400
C1—C8	1.512 (3)	O4—C15	1.377 (2)
C2—C3	1.383 (3)	O4—HO4	0.8400
C2—H2	0.9500	C11—C12	1.392 (3)
C3—C4	1.385 (3)	C11—C16	1.393 (3)
C3—H3	0.9500	C12—C13	1.397 (3)
C4—C5	1.397 (3)	C12—H12	0.9500
C4—H4	0.9500	C13—C14	1.390 (3)
C5—C6	1.505 (3)	C13—H13	0.9500
C6—C7	1.496 (3)	C14—C15	1.389 (3)
C7—H7A	0.9800	C14—H14	0.9500
C7—H7B	0.9800	C15—C16	1.393 (3)
C7—H7C	0.9800	C16—H16	0.9500
C8—C9	1.494 (3)
C5—N1—C1	117.35 (18)	C9—C8—C1	118.19 (19)
N1—C1—C2	122.87 (19)	C8—C9—H9A	109.5
N1—C1—C8	117.01 (19)	C8—C9—H9B	109.5
C2—C1—C8	120.12 (19)	H9A—C9—H9B	109.5
C3—C2—C1	119.2 (2)	C8—C9—H9C	109.5
C3—C2—H2	120.4	H9A—C9—H9C	109.5
C1—C2—H2	120.4	H9B—C9—H9C	109.5
C2—C3—C4	118.4 (2)	C11—O3—HO3	109.5
C2—C3—H3	120.8	C15—O4—HO4	109.5
C4—C3—H3	120.8	O3—C11—C12	122.26 (19)
C3—C4—C5	119.18 (19)	O3—C11—C16	117.1 (2)
C3—C4—H4	120.4	C12—C11—C16	120.7 (2)
C5—C4—H4	120.4	C11—C12—C13	118.9 (2)
N1—C5—C4	122.97 (19)	C11—C12—H12	120.6
N1—C5—C6	116.70 (19)	C13—C12—H12	120.6
C4—C5—C6	120.33 (18)	C14—C13—C12	121.1 (2)
O1—C6—C7	122.1 (2)	C14—C13—H13	119.4
O1—C6—C5	119.5 (2)	C12—C13—H13	119.4
C7—C6—C5	118.45 (18)	C15—C14—C13	119.2 (2)
C6—C7—H7A	109.5	C15—C14—H14	120.4
C6—C7—H7B	109.5	C13—C14—H14	120.4
H7A—C7—H7B	109.5	O4—C15—C14	122.4 (2)
C6—C7—H7C	109.5	O4—C15—C16	116.9 (2)
H7A—C7—H7C	109.5	C14—C15—C16	120.7 (2)
H7B—C7—H7C	109.5	C15—C16—C11	119.4 (2)
O2—C8—C9	122.80 (19)	C15—C16—H16	120.3
O2—C8—C1	119.0 (2)	C11—C16—H16	120.3
C5—N1—C1—C2	−0.9 (3)	N1—C1—C8—O2	−176.44 (19)
C5—N1—C1—C8	179.22 (17)	C2—C1—C8—O2	3.7 (3)
N1—C1—C2—C3	1.7 (3)	N1—C1—C8—C9	3.7 (3)
C8—C1—C2—C3	−178.40 (19)	C2—C1—C8—C9	−176.1 (2)
C1—C2—C3—C4	−0.4 (3)	O3—C11—C12—C13	179.6 (2)
C2—C3—C4—C5	−1.6 (3)	C16—C11—C12—C13	−0.7 (3)
C1—N1—C5—C4	−1.2 (3)	C11—C12—C13—C14	0.1 (3)
C1—N1—C5—C6	178.93 (17)	C12—C13—C14—C15	0.2 (3)
C3—C4—C5—N1	2.5 (3)	C13—C14—C15—O4	179.3 (2)
C3—C4—C5—C6	−177.67 (19)	C13—C14—C15—C16	0.2 (3)
N1—C5—C6—O1	−178.45 (19)	O4—C15—C16—C11	−179.94 (19)
C4—C5—C6—O1	1.7 (3)	C14—C15—C16—C11	−0.8 (3)
N1—C5—C6—C7	0.3 (3)	O3—C11—C16—C15	−179.2 (2)
C4—C5—C6—C7	−179.55 (19)	C12—C11—C16—C15	1.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O3—HO3···O2	0.84	1.95	2.784 (2)	174
O4—HO4···O1i	0.84	1.96	2.802 (3)	177

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—HO3⋯O2	0.84	1.95	2.784 (2)	174
O4—HO4⋯O1i	0.84	1.96	2.802 (3)	177

Symmetry code: (i) .