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

Arman, H.D.; Kaulgud, T.; Tiekink, E.R.T.

doi:10.1107/S1600536810038390

organic compounds

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Volume 66| Part 10| October 2010| Page o2684

doi:10.1107/S1600536810038390

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

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

^aDepartment of Chemistry, The University of Texas at San Antonio, One UTSA Circle, San Antonio, Texas 78249-0698, USA, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 24 September 2010; accepted 25 September 2010; online 30 September 2010)

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, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.051
wR(F²) = 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

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) x+1, y, z; (ii) x-1, y, z; (iii) -x+1, -y, -z+1.

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 ).

Supporting information

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

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

checkCIF report

Comment top

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.

Related literature top

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

Experimental top

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).

Computing details top

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2005); cell refinement: CrystalClear (Molecular Structure Corporation & Rigaku, 2005); data reduction: CrystalClear (Molecular Structure Corporation & Rigaku, 2005); 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).

Figures top

	Fig. 1. Molecular structure of 2-phenylacetic acid found in co-crystal (I) showing displacement ellipsoids at the 50% probability level
	Fig. 2. Molecular structure of 3-pyridinealdazine found in co-crystal (I) showing displacement ellipsoids at the 50% probability level. The molecule is disposed about a centre of inversion with i = 1 - x, 1 - y, -z.
	Fig. 3. The three component aggregate in (I) highlighting the extended chair conformation. The O—H···N hydrogen bonds are shown as orange dashed lines.
	Fig. 4. A view in projection down the a axis highlighting the stacking of layers in co-crystal (I) mediated by O—H···N, C—H···O and C—H···π interactions shown as orange, blue and purple dashed lines, respectively.

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

Crystal data top

C₁₂H₁₀N₄·2C₈H₈O₂	Z = 1
M_r = 482.53	F(000) = 254
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0606P)² + 0.17P] where P = (F_o² + 2F_c²)/3
2849 reflections	(Δ/σ)_max = 0.001
166 parameters	Δρ_max = 0.24 e Å⁻³
1 restraint	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₂H₁₀N₄·2C₈H₈O₂	γ = 76.46 (2)°
M_r = 482.53	V = 626.1 (5) Å³
Triclinic, P1	Z = 1
a = 5.511 (2) Å	Mo Kα radiation
b = 9.536 (4) Å	µ = 0.09 mm⁻¹
c = 12.434 (6) Å	T = 98 K
α = 80.30 (2)°	0.52 × 0.32 × 0.10 mm
β = 88.45 (3)°

Data collection top

Rigaku AFC12K/SATURN724 diffractometer	2849 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2578 reflections with I > 2σ(I)
T_min = 0.832, T_max = 1.000	R_int = 0.026
5606 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	1 restraint
wR(F²) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	Δρ_max = 0.24 e Å⁻³
2849 reflections	Δρ_min = −0.21 e Å⁻³
166 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry code: (i) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

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···O2^iv	0.95	2.57	3.277 (2)	132
C10—H10···Cg1^iv	0.95	2.89	3.627 (2)	135

Symmetry codes: (ii) x+1, y, z; (iii) x−1, y, z; (iv) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₀N₄·2C₈H₈O₂
M_r	482.53
Crystal system, space group	Triclinic, P1
Temperature (K)	98
a, b, c (Å)	5.511 (2), 9.536 (4), 12.434 (6)
α, β, γ (°)	80.30 (2), 88.45 (3), 76.46 (2)
V (Å³)	626.1 (5)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.52 × 0.32 × 0.10

Data collection
Diffractometer	Rigaku AFC12K/SATURN724 diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.832, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	5606, 2849, 2578
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.130, 1.09
No. of reflections	2849
No. of parameters	166
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.21

Computer programs: CrystalClear (Molecular Structure Corporation & Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C3–C8 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···N1ⁱ	0.852 (15)	1.838 (15)	2.689 (2)	175.8 (19)
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) x+1, y, z; (ii) x−1, y, z; (iii) −x+1, −y, −z+1.

References

Arman, H. D., Kaulgud, T. & Tiekink, E. R. T. (2010a). Acta Cryst. E66, o2356. Web of Science CSD CrossRef IUCr Journals Google Scholar
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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page o2684

doi:10.1107/S1600536810038390

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

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