2-Phenyl-acetic acid-3-{(E)-2-[(E)-pyridin-3-yl-methyl-idene]hydrazin-1-ylidenemeth-yl}pyridine (2/1).

The asymmetric unit of the title 1:2 adduct, C(12)H(10)N(4)·2C(8)H(8)O(2), comprises a single mol-ecule of 2-phenyl-acetic acid and half a mol-ecule of 3-pyridine-aldazine; the latter is completed by crystallographic inversion symmetry. In the crystal, mol-ecules are connected into a three-component aggregate via O-H⋯N hydrogen bonds. As the carboxyl group lies above the plane through the benzene ring to which it is attached [C-C-C-C = 62.24 (17)°] and the 4-pyridine-aldazine mol-ecule is almost planar (r.m.s. deviation of the 16 non-H atoms = 0.027 Å), the overall shape of the aggregate is that of a flattened extended chair. Layers of these aggregates are connected by C-H⋯O and C-H⋯π inter-actions and stack parallel to (220).

Related literature

For related studies on co-crystal formation involving the isomeric n-pyridine­aldazines, see: Broker et al. (2008 ▶); Arman et al. (2010a ▶,b ▶).

Experimental

Crystal data

C12H10N4·2C8H8O2

M = 482.53

Triclinic,

a = 5.511 (2) Å

b = 9.536 (4) Å

c = 12.434 (6) Å

α = 80.30 (2)°

β = 88.45 (3)°

γ = 76.46 (2)°

V = 626.1 (5) Å3

Z = 1

Mo Kα radiation

μ = 0.09 mm−1

T = 98 K

0.52 × 0.32 × 0.10 mm

Data collection

Rigaku AFC12/SATURN724 diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.832, T max = 1.000

5606 measured reflections

2849 independent reflections

2578 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.130

S = 1.09

2849 reflections

166 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrystalClear (Molecular Structure Corporation & 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: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810038390/hb5648sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810038390/hb5648Isup2.hkl

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

C12H10N4·2C8H8O2	Z = 1
Mr = 482.53	F(000) = 254
Triclinic, P1	Dx = 1.280 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.511 (2) Å	Cell parameters from 2727 reflections
b = 9.536 (4) Å	θ = 2.6–40.1°
c = 12.434 (6) Å	µ = 0.09 mm−1
α = 80.30 (2)°	T = 98 K
β = 88.45 (3)°	Prism, gold
γ = 76.46 (2)°	0.52 × 0.32 × 0.10 mm
V = 626.1 (5) Å3

Rigaku AFC12K/SATURN724 diffractometer	2849 independent reflections
Radiation source: fine-focus sealed tube	2578 reflections with I > 2σ(I)
graphite	Rint = 0.026
ω scans	θmax = 27.5°, θmin = 2.6°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −6→7
Tmin = 0.832, Tmax = 1.000	k = −11→12
5606 measured reflections	l = −16→16

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.0606P)2 + 0.17P] where P = (Fo2 + 2Fc2)/3
2849 reflections	(Δ/σ)max = 0.001
166 parameters	Δρmax = 0.24 e Å−3
1 restraint	Δρmin = −0.21 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
O1	0.4813 (2)	0.37678 (11)	0.41019 (8)	0.0306 (3)
H1o	0.616 (2)	0.346 (2)	0.3774 (15)	0.046*
O2	0.65187 (19)	0.18266 (12)	0.53456 (8)	0.0327 (3)
C1	0.4823 (3)	0.28746 (15)	0.50429 (11)	0.0244 (3)
C2	0.2466 (2)	0.33170 (15)	0.56825 (11)	0.0260 (3)
H2A	0.2104	0.4387	0.5669	0.031*
H2B	0.1059	0.3105	0.5311	0.031*
C3	0.2583 (2)	0.25628 (14)	0.68565 (11)	0.0233 (3)
C4	0.4322 (3)	0.27578 (15)	0.75870 (11)	0.0260 (3)
H4	0.5476	0.3337	0.7336	0.031*
C5	0.4367 (3)	0.21091 (16)	0.86760 (12)	0.0301 (3)
H5	0.5550	0.2247	0.9166	0.036*
C6	0.2690 (3)	0.12602 (18)	0.90514 (12)	0.0339 (3)
H6	0.2706	0.0829	0.9799	0.041*
C7	0.0988 (3)	0.10450 (18)	0.83273 (13)	0.0347 (4)
H7	−0.0142	0.0450	0.8577	0.042*
C8	0.0934 (2)	0.16981 (16)	0.72377 (12)	0.0284 (3)
H8	−0.0244	0.1551	0.6749	0.034*
N1	−0.0907 (2)	0.29342 (13)	0.30452 (10)	0.0282 (3)
N2	0.4880 (2)	0.43938 (12)	0.03906 (9)	0.0258 (3)
C9	0.0632 (3)	0.16205 (16)	0.33502 (12)	0.0296 (3)
H9	0.0136	0.0960	0.3926	0.035*
C10	0.2924 (3)	0.11778 (16)	0.28634 (12)	0.0305 (3)
H10	0.3954	0.0231	0.3097	0.037*
C11	0.3679 (3)	0.21366 (15)	0.20351 (12)	0.0276 (3)
H11	0.5233	0.1859	0.1687	0.033*
C12	0.2118 (3)	0.35235 (15)	0.17169 (11)	0.0241 (3)
C13	−0.0167 (3)	0.38574 (15)	0.22392 (11)	0.0266 (3)
H13	−0.1254	0.4788	0.2011	0.032*
C14	0.2776 (3)	0.46341 (15)	0.08762 (11)	0.0253 (3)
H14	0.1624	0.5551	0.0685	0.030*

	U11	U22	U33	U12	U13	U23
O1	0.0334 (6)	0.0296 (5)	0.0252 (5)	−0.0036 (4)	0.0036 (4)	−0.0007 (4)
O2	0.0301 (5)	0.0331 (6)	0.0281 (5)	0.0021 (4)	0.0024 (4)	0.0004 (4)
C1	0.0267 (6)	0.0245 (6)	0.0224 (6)	−0.0067 (5)	−0.0020 (5)	−0.0038 (5)
C2	0.0231 (6)	0.0258 (7)	0.0265 (7)	−0.0022 (5)	−0.0011 (5)	−0.0019 (5)
C3	0.0214 (6)	0.0223 (6)	0.0242 (7)	0.0001 (5)	0.0008 (5)	−0.0054 (5)
C4	0.0254 (6)	0.0227 (6)	0.0293 (7)	−0.0025 (5)	−0.0006 (5)	−0.0062 (5)
C5	0.0280 (7)	0.0319 (7)	0.0281 (7)	0.0025 (6)	−0.0030 (5)	−0.0114 (6)
C6	0.0312 (7)	0.0391 (8)	0.0242 (7)	0.0028 (6)	0.0036 (5)	−0.0013 (6)
C7	0.0255 (7)	0.0376 (8)	0.0366 (8)	−0.0053 (6)	0.0057 (6)	0.0019 (6)
C8	0.0212 (6)	0.0315 (7)	0.0314 (7)	−0.0044 (5)	−0.0010 (5)	−0.0043 (6)
N1	0.0316 (6)	0.0279 (6)	0.0253 (6)	−0.0074 (5)	0.0043 (5)	−0.0051 (5)
N2	0.0309 (6)	0.0236 (6)	0.0229 (6)	−0.0070 (5)	0.0021 (4)	−0.0030 (5)
C9	0.0374 (8)	0.0241 (7)	0.0276 (7)	−0.0091 (6)	0.0017 (6)	−0.0029 (5)
C10	0.0354 (8)	0.0224 (7)	0.0318 (7)	−0.0037 (6)	0.0017 (6)	−0.0039 (6)
C11	0.0281 (7)	0.0253 (7)	0.0290 (7)	−0.0039 (5)	0.0024 (5)	−0.0070 (5)
C12	0.0275 (7)	0.0227 (6)	0.0224 (6)	−0.0056 (5)	0.0006 (5)	−0.0052 (5)
C13	0.0290 (7)	0.0242 (7)	0.0250 (7)	−0.0030 (5)	0.0012 (5)	−0.0042 (5)
C14	0.0280 (7)	0.0229 (6)	0.0244 (6)	−0.0042 (5)	−0.0005 (5)	−0.0045 (5)

O1—C1	1.3254 (17)	C7—H7	0.9500
O1—H1o	0.853 (9)	C8—H8	0.9500
O2—C1	1.2120 (17)	N1—C9	1.3389 (19)
C1—C2	1.516 (2)	N1—C13	1.3397 (18)
C2—C3	1.5105 (19)	N2—C14	1.2832 (19)
C2—H2A	0.9900	N2—N2i	1.408 (2)
C2—H2B	0.9900	C9—C10	1.391 (2)
C3—C8	1.388 (2)	C9—H9	0.9500
C3—C4	1.4019 (19)	C10—C11	1.381 (2)
C4—C5	1.389 (2)	C10—H10	0.9500
C4—H4	0.9500	C11—C12	1.398 (2)
C5—C6	1.388 (2)	C11—H11	0.9500
C5—H5	0.9500	C12—C13	1.395 (2)
C6—C7	1.390 (2)	C12—C14	1.4602 (19)
C6—H6	0.9500	C13—H13	0.9500
C7—C8	1.390 (2)	C14—H14	0.9500
C1—O1—H1O	107.8 (14)	C8—C7—H7	119.9
O2—C1—O1	123.54 (13)	C3—C8—C7	120.66 (14)
O2—C1—C2	124.48 (13)	C3—C8—H8	119.7
O1—C1—C2	111.98 (12)	C7—C8—H8	119.7
C3—C2—C1	114.69 (11)	C9—N1—C13	117.66 (13)
C3—C2—H2A	108.6	C14—N2—N2i	111.72 (14)
C1—C2—H2A	108.6	N1—C9—C10	123.08 (13)
C3—C2—H2B	108.6	N1—C9—H9	118.5
C1—C2—H2B	108.6	C10—C9—H9	118.5
H2A—C2—H2B	107.6	C11—C10—C9	118.95 (13)
C8—C3—C4	118.88 (13)	C11—C10—H10	120.5
C8—C3—C2	120.74 (12)	C9—C10—H10	120.5
C4—C3—C2	120.37 (13)	C10—C11—C12	118.88 (13)
C5—C4—C3	120.36 (14)	C10—C11—H11	120.6
C5—C4—H4	119.8	C12—C11—H11	120.6
C3—C4—H4	119.8	C13—C12—C11	117.99 (13)
C6—C5—C4	120.29 (14)	C13—C12—C14	118.80 (12)
C6—C5—H5	119.9	C11—C12—C14	123.21 (13)
C4—C5—H5	119.9	N1—C13—C12	123.42 (13)
C5—C6—C7	119.58 (14)	N1—C13—H13	118.3
C5—C6—H6	120.2	C12—C13—H13	118.3
C7—C6—H6	120.2	N2—C14—C12	121.22 (13)
C6—C7—C8	120.21 (15)	N2—C14—H14	119.4
C6—C7—H7	119.9	C12—C14—H14	119.4
O2—C1—C2—C3	13.2 (2)	C13—N1—C9—C10	−0.6 (2)
O1—C1—C2—C3	−167.21 (12)	N1—C9—C10—C11	0.8 (2)
C1—C2—C3—C8	−119.47 (14)	C9—C10—C11—C12	0.3 (2)
C1—C2—C3—C4	62.24 (17)	C10—C11—C12—C13	−1.5 (2)
C8—C3—C4—C5	−0.8 (2)	C10—C11—C12—C14	177.93 (13)
C2—C3—C4—C5	177.55 (12)	C9—N1—C13—C12	−0.7 (2)
C3—C4—C5—C6	0.0 (2)	C11—C12—C13—N1	1.8 (2)
C4—C5—C6—C7	0.9 (2)	C14—C12—C13—N1	−177.69 (13)
C5—C6—C7—C8	−1.2 (2)	N2i—N2—C14—C12	179.76 (13)
C4—C3—C8—C7	0.5 (2)	C13—C12—C14—N2	178.28 (13)
C2—C3—C8—C7	−177.80 (13)	C11—C12—C14—N2	−1.1 (2)
C6—C7—C8—C3	0.5 (2)

Cg1 is the centroid of the C3–C8 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···N1ii	0.85 (2)	1.84 (2)	2.689 (2)	176 (2)
C8—H8···O2iii	0.95	2.47	3.398 (2)	166
C10—H10···O2iv	0.95	2.57	3.277 (2)	132
C10—H10···Cg1iv	0.95	2.89	3.627 (2)	135

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C3–C8 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯N1i	0.85 (2)	1.84 (2)	2.689 (2)	176 (2)
C8—H8⋯O2ii	0.95	2.47	3.398 (2)	166
C10—H10⋯O2iii	0.95	2.57	3.277 (2)	132
C10—H10⋯Cg1iii	0.95	2.89	3.627 (2)	135

Symmetry codes: (i) ; (ii) ; (iii) .