Literature DB >> 21589098

Benzoic acid-4-{(1E)-[(E)-2-(pyridin-4-yl-methyl-idene)hydrazin-1-yl-idene]meth-yl}pyridine (2/1).

Hadi D Arman, Trupta Kaulgud, Edward R T Tiekink.

Abstract

In the title co-crystal, C(12)H(10)N(4)·2C(7)H(6)O(2), the complete 4-pyridine-aldazine mol-ecule is generated by a crystallographic centre of inversion. In the crystal, mol-ecules are connected into a three component aggregate via O-H⋯N hydrogen bonds. As both the benzoic acid [O-C-C-C torsion angle = 174.8 (2)°] and 4-pyridine-aldazine (r.m.s. deviation of the 16 non-H atoms = 0.041 Å) mol-ecules are almost planar, the resulting three-component aggregate is essentially planar. The crystal packing comprises layers of the three-component aggregates of alternating orientation stacked along the b axis; the connections between the mol-ecules are of the types C-H⋯π and π-π [pyridine-benzene centroid-centroid distance = 3.787 (4) Å].

Entities: Chemical Disease Species

Year: 2010 PMID： 21589098 PMCID： PMC3009056 DOI： 10.1107/S1600536810041875

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

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

C12H10N4·2C7H6O2 M = 454.48 Monoclinic, a = 6.873 (6) Å b = 26.059 (19) Å c = 7.117 (6) Å β = 116.245 (13)° V = 1143.3 (16) Å3 Z = 2 Mo Kα radiation μ = 0.09 mm−1 T = 98 K 0.40 × 0.26 × 0.08 mm

Data collection

Rigaku AFC12/SATURN724 diffractometer 6111 measured reflections 1956 independent reflections 1620 reflections with I > 2σ(I) R int = 0.063

Refinement

R[F 2 > 2σ(F 2)] = 0.072 wR(F 2) = 0.191 S = 1.12 1956 reflections 157 parameters 1 restraint H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.30 e Å−3 Δρmin = −0.28 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/S1600536810041875/hb5684sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810041875/hb5684Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₂H₁₀N₄·2C₇H₆O₂	F(000) = 476
M_r = 454.48	D_x = 1.320 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4161 reflections
a = 6.873 (6) Å	θ = 3.3–40.2°
b = 26.059 (19) Å	µ = 0.09 mm⁻¹
c = 7.117 (6) Å	T = 98 K
β = 116.245 (13)°	Block, yellow
V = 1143.3 (16) Å³	0.40 × 0.26 × 0.08 mm
Z = 2

Rigaku AFC12K/SATURN724 diffractometer	1620 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.063
graphite	θ_max = 25.0°, θ_min = 3.1°
ω scans	h = −8→8
6111 measured reflections	k = −30→30
1956 independent reflections	l = −8→6

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)] = 0.072	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.191	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ²(F_o²) + (0.083P)² + 0.7947P] where P = (F_o² + 2F_c²)/3
1956 reflections	(Δ/σ)_max < 0.001
157 parameters	Δρ_max = 0.30 e Å⁻³
1 restraint	Δρ_min = −0.28 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	U_iso*/U_eq
O1	0.2366 (3)	0.14824 (8)	0.4031 (3)	0.0367 (5)
H1o	0.254 (6)	0.1339 (13)	0.305 (4)	0.055*
O2	−0.0291 (3)	0.09135 (7)	0.3447 (3)	0.0348 (5)
C1	0.0732 (4)	0.12953 (10)	0.4330 (4)	0.0279 (6)
C2	0.0247 (4)	0.15989 (10)	0.5862 (4)	0.0272 (6)
C3	−0.1544 (5)	0.14691 (10)	0.6194 (4)	0.0294 (6)
H3	−0.2428	0.1185	0.5480	0.035*
C4	−0.2032 (5)	0.17572 (11)	0.7573 (4)	0.0363 (7)
H4	−0.3265	0.1673	0.7784	0.044*
C5	−0.0723 (6)	0.21684 (12)	0.8644 (5)	0.0422 (8)
H5	−0.1061	0.2363	0.9591	0.051*
C6	0.1078 (6)	0.22960 (12)	0.8335 (5)	0.0415 (8)
H6	0.1974	0.2576	0.9074	0.050*
C7	0.1563 (5)	0.20132 (11)	0.6942 (4)	0.0334 (7)
H7	0.2788	0.2101	0.6723	0.040*
N1	0.2915 (4)	0.09852 (9)	1.1065 (3)	0.0308 (6)
N2	0.5060 (4)	0.01762 (9)	0.5783 (3)	0.0316 (6)
C8	0.3397 (4)	0.03986 (10)	0.8005 (4)	0.0268 (6)
C9	0.1647 (4)	0.03201 (10)	0.8464 (4)	0.0285 (6)
H9	0.0594	0.0065	0.7743	0.034*
C10	0.1466 (5)	0.06209 (10)	0.9991 (4)	0.0312 (7)
H10	0.0264	0.0567	1.0288	0.037*
C11	0.4597 (4)	0.10580 (11)	1.0616 (4)	0.0293 (6)
H11	0.5632	0.1315	1.1365	0.035*
C12	0.4898 (5)	0.07771 (10)	0.9114 (4)	0.0297 (6)
H12	0.6110	0.0842	0.8843	0.036*
C13	0.3593 (4)	0.00791 (10)	0.6385 (4)	0.0278 (6)
H13	0.2627	−0.0200	0.5783	0.033*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0403 (12)	0.0415 (12)	0.0340 (12)	−0.0088 (9)	0.0215 (9)	−0.0103 (9)
O2	0.0347 (11)	0.0351 (11)	0.0342 (11)	−0.0036 (9)	0.0150 (9)	−0.0074 (8)
C1	0.0293 (14)	0.0281 (14)	0.0218 (14)	0.0032 (11)	0.0073 (11)	0.0008 (10)
C2	0.0322 (14)	0.0282 (14)	0.0206 (13)	0.0035 (11)	0.0112 (11)	0.0028 (10)
C3	0.0353 (15)	0.0253 (14)	0.0256 (14)	0.0018 (11)	0.0116 (11)	0.0043 (11)
C4	0.0401 (17)	0.0392 (16)	0.0346 (16)	0.0054 (13)	0.0210 (13)	0.0058 (12)
C5	0.059 (2)	0.0381 (17)	0.0346 (17)	0.0030 (15)	0.0255 (15)	−0.0042 (13)
C6	0.0503 (19)	0.0390 (17)	0.0370 (17)	−0.0072 (14)	0.0210 (14)	−0.0098 (13)
C7	0.0371 (16)	0.0337 (16)	0.0293 (15)	−0.0027 (12)	0.0145 (12)	−0.0005 (11)
N1	0.0353 (13)	0.0328 (13)	0.0241 (12)	0.0048 (10)	0.0130 (10)	0.0024 (9)
N2	0.0405 (14)	0.0303 (13)	0.0235 (12)	0.0005 (10)	0.0138 (11)	−0.0029 (9)
C8	0.0301 (14)	0.0278 (14)	0.0211 (13)	0.0076 (11)	0.0100 (11)	0.0044 (10)
C9	0.0313 (14)	0.0321 (14)	0.0198 (13)	0.0020 (11)	0.0091 (11)	0.0013 (10)
C10	0.0295 (15)	0.0341 (15)	0.0286 (15)	0.0027 (11)	0.0115 (12)	0.0031 (11)
C11	0.0300 (14)	0.0302 (14)	0.0250 (14)	0.0018 (11)	0.0098 (11)	0.0002 (10)
C12	0.0298 (14)	0.0323 (15)	0.0263 (14)	0.0024 (11)	0.0118 (12)	0.0011 (11)
C13	0.0328 (14)	0.0246 (13)	0.0234 (14)	0.0025 (11)	0.0100 (11)	0.0022 (10)

O1—C1	1.325 (3)	N1—C11	1.342 (4)
O1—H1O	0.85 (3)	N1—C10	1.343 (4)
O2—C1	1.220 (3)	N2—C13	1.283 (4)
C1—C2	1.499 (4)	N2—N2ⁱ	1.418 (4)
C2—C3	1.395 (4)	C8—C12	1.393 (4)
C2—C7	1.400 (4)	C8—C9	1.394 (4)
C3—C4	1.389 (4)	C8—C13	1.476 (4)
C3—H3	0.9500	C9—C10	1.390 (4)
C4—C5	1.390 (4)	C9—H9	0.9500
C4—H4	0.9500	C10—H10	0.9500
C5—C6	1.390 (5)	C11—C12	1.384 (4)
C5—H5	0.9500	C11—H11	0.9500
C6—C7	1.389 (4)	C12—H12	0.9500
C6—H6	0.9500	C13—H13	0.9500
C7—H7	0.9500

C1—O1—H1o	114 (3)	C2—C7—H7	120.0
O2—C1—O1	123.6 (3)	C11—N1—C10	117.7 (2)
O2—C1—C2	122.8 (3)	C13—N2—N2ⁱ	110.7 (3)
O1—C1—C2	113.6 (2)	C12—C8—C9	118.1 (2)
C3—C2—C7	119.9 (3)	C12—C8—C13	122.8 (3)
C3—C2—C1	119.5 (2)	C9—C8—C13	119.1 (2)
C7—C2—C1	120.6 (3)	C10—C9—C8	119.0 (3)
C4—C3—C2	119.7 (3)	C10—C9—H9	120.5
C4—C3—H3	120.1	C8—C9—H9	120.5
C2—C3—H3	120.1	N1—C10—C9	122.9 (3)
C3—C4—C5	120.3 (3)	N1—C10—H10	118.5
C3—C4—H4	119.8	C9—C10—H10	118.5
C5—C4—H4	119.8	N1—C11—C12	123.2 (3)
C6—C5—C4	120.2 (3)	N1—C11—H11	118.4
C6—C5—H5	119.9	C12—C11—H11	118.4
C4—C5—H5	119.9	C11—C12—C8	119.1 (3)
C5—C6—C7	119.8 (3)	C11—C12—H12	120.5
C5—C6—H6	120.1	C8—C12—H12	120.5
C7—C6—H6	120.1	N2—C13—C8	120.4 (2)
C6—C7—C2	120.1 (3)	N2—C13—H13	119.8
C6—C7—H7	120.0	C8—C13—H13	119.8

O2—C1—C2—C3	−5.1 (4)	C12—C8—C9—C10	0.2 (4)
O1—C1—C2—C3	174.8 (2)	C13—C8—C9—C10	180.0 (2)
O2—C1—C2—C7	175.5 (2)	C11—N1—C10—C9	0.3 (4)
O1—C1—C2—C7	−4.6 (4)	C8—C9—C10—N1	−0.4 (4)
C7—C2—C3—C4	1.0 (4)	C10—N1—C11—C12	0.0 (4)
C1—C2—C3—C4	−178.4 (2)	N1—C11—C12—C8	−0.1 (4)
C2—C3—C4—C5	−1.0 (4)	C9—C8—C12—C11	0.1 (4)
C3—C4—C5—C6	0.3 (4)	C13—C8—C12—C11	−179.7 (2)
C4—C5—C6—C7	0.3 (5)	N2ⁱ—N2—C13—C8	−179.7 (2)
C5—C6—C7—C2	−0.3 (5)	C12—C8—C13—N2	−7.2 (4)
C3—C2—C7—C6	−0.3 (4)	C9—C8—C13—N2	173.0 (2)
C1—C2—C7—C6	179.1 (2)

Cg1 is the centroid of the C2–C7 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···N1ⁱⁱ	0.85 (3)	1.80 (3)	2.642 (4)	175 (4)
C6—H6···Cg1ⁱⁱⁱ	0.95	2.64	3.540 (5)	159

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C2–C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯N1ⁱ	0.85 (3)	1.80 (3)	2.642 (4)	175 (4)
C6—H6⋯Cg1ⁱⁱ	0.95	2.64	3.540 (5)	159

Symmetry codes: (i) ; (ii) .

3 in total

Benzoic acid-4-{(1E)-[(E)-2-(pyridin-4-yl-methyl-idene)hydrazin-1-yl-idene]meth-yl}pyridine (2/1).

Related literature

Experimental

Crystal data

Data collection

Refinement

1. A short history of SHELX.

2. 2-Phenyl-acetic acid-(E,E)-4,4'-(hydra-zinediylidene)dipyridine (2/1).

3. 2-(4-Chloro-phen-yl)acetic acid-2-{(E)-[(E)-2-(2-pyridyl-methyl-idene)hydrazin-1-yl-idene]meth-yl}pyridine (1/1).