2-Phenyl­acetic acid–3-{(E)-2-[(E)-pyridin-3-yl­methyl­idene]hydrazin-1-ylidenemeth­yl}pyridine (2/1)

Hadi D Arman; Trupta Kaulgud; Edward R T Tiekink

doi:10.1107/S1600536810038390

. 2010 Sep 30;66(Pt 10):o2684. doi: 10.1107/S1600536810038390

2-Phenylacetic acid–3-{(E)-2-[(E)-pyridin-3-ylmethylidene]hydrazin-1-ylidenemethyl}pyridine (2/1)

Hadi D Arman ^a, Trupta Kaulgud ^a, Edward R T Tiekink ^b,^*

PMCID: PMC2983166 PMID: 21587652

Abstract

The asymmetric unit of the title 1:2 adduct, C₁₂H₁₀N₄·2C₈H₈O₂, comprises a single molecule of 2-phenylacetic acid and half a molecule of 3-pyridinealdazine; the latter is completed by crystallographic inversion symmetry. In the crystal, molecules 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-pyridinealdazine molecule 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 interactions 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 _r = 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
Δρ_max = 0.24 e Å⁻³
Δρ_min = −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 ▶).

Supplementary Material

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

e-66-o2684-sup1.cif^{(17KB, cif)}

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

e-66-o2684-Isup2.hkl^{(137KB, hkl)}

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

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

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

supplementary crystallographic information

Comment

As a continuation of studies into the phenomenon of co-crystallization of the isomeric n-pyridinealdazines (Broker et al., 2008; Arman et al., 2010a; Arman et al., 2010b), the co-crystallization of 2-phenylacetic acid and 3-pyridinealdazine was investigated. This lead to the isolation of the title 2/1 co-crystal, (I).

The asymmetric unit in (I) comprises a molecule of 2-phenylacetic acid, Fig. 1, and half a molecule of 3-pyridinealdazine, with the latter disposed about a centre of inversion, Fig. 2. The constituents of (I) are connected by O—H···N hydrogen bonds, Table 1, to generate a centrosymmetric three component aggregate, Fig. 3. The 2-phenylacetic acid molecule is non-planar as seen in the value of the C1—C2—C3—C4 torsion angle of 62.24 (17) °. By contrast, the 4-pyridinealdazine molecule is planar with the r.m.s. deviation of the 16 non-hydrogen atoms from their least-squares plane being 0.027 Å. Hence, the three component aggregate has the shape of a flattened extended chair. The structure of co-crystal (I) resembles closely that with 4-pyridinealdazine (Arman et al., 2010b) but the structures are not isomorphous.

In the crystal packing, the three component aggregates pack into layers parallel to (022) being connected by C—H···O and C—H···π contacts, Fig. 4 and Table 1.

Experimental

Golden prisms of (I) were isolated from the 2:1 co-crystallization of 2-phenylacetic acid (Sigma Aldrich) and 3-[(1E)-[(E)-2-(pyridin-3-ylmethylidene)hydrazin-1-ylidene]methyl]pyridine (Sigma Aldrich) in tetrahydrofuran, m. pt. 370–373 K.

IR assignment (cm^-1): 2923 ν(C—H); 2444 ν(O—H); 1704 ν(C=O); 1628 ν(C=N); 1498, 1455, 1410 ν(C–C aromatic); 1346, 1307 ν(C—N); 819, 746 δ(C—H).