Di-4-pyridyl sulfide–isophthalic acid (1/1)

Jian-Hua Qin; Xiao-Dong Li; Jian-Ge Wang

doi:10.1107/S1600536808035496

. 2008 Nov 8;64(Pt 12):o2279. doi: 10.1107/S1600536808035496

Di-4-pyridyl sulfide–isophthalic acid (1/1)

Jian-Hua Qin ^a,^*, Xiao-Dong Li ^a, Jian-Ge Wang ^a

PMCID: PMC2960055 PMID: 21581259

Abstract

In the heteromolecular title structure, C₁₀H₈N₂S·C₈H₆O₄, the two components are linked by O—H⋯N hydrogen bonds to form a one-dimensional chain. These chains are further interconnected by weak intermolecular C—H⋯O hydrogen bonds and weak C—H⋯π interactions to generate a three-dimensional supramolecular structure.

Related literature

For C—H⋯O hydrogen bonds, see: Bhogala et al. (2005 ▶); Wang et al. (2008 ▶). For C—H⋯π interactions, see: Fun & Kia (2008 ▶).

Experimental

Crystal data

C₁₀H₈N₂S·C₈H₆O₄
M _r = 354.37
Triclinic,
a = 6.618 (6) Å
b = 8.200 (7) Å
c = 16.013 (13) Å
α = 88.808 (11)°
β = 79.340 (11)°
γ = 79.275 (11)°
V = 839.0 (12) Å³
Z = 2
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 291 (2) K
0.47 × 0.30 × 0.11 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T _min = 0.905, T _max = 0.977
6280 measured reflections
3084 independent reflections
1885 reflections with I > 2σ(I)
R _int = 0.020

Refinement

R[F ² > 2σ(F ²)] = 0.080
wR(F ²) = 0.269
S = 1.08
3084 reflections
228 parameters
H-atom parameters constrained
Δρ_max = 1.05 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808035496/si2125sup1.cif

e-64-o2279-sup1.cif^{(17.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808035496/si2125Isup2.hkl

e-64-o2279-Isup2.hkl^{(151.3KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17⋯O2ⁱ	0.93	2.45	3.334 (6)	159
C16—H16⋯O2ⁱⁱ	0.93	2.58	3.180 (6)	123
C13—H13⋯O4ⁱⁱⁱ	0.93	2.31	3.141 (6)	148
C12—H12⋯Cg1^iv	0.93	2.98	3.570 (6)	123
O3—H3D⋯N1^v	0.82	1.83	2.634 (5)	164
O1—H1D⋯N2^vi	0.82	1.84	2.662 (5)	179

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) ; (vi) . Cg1 is the centroid of the C2–C7 isophthalic acid ring.

Acknowledgments

The authors thank Luo Yang Normal University for supporting this work.

supplementary crystallographic information

Comment

The asymmetric unit consists of one 4,4'-dipyridyl sulfide molecule and one isophthalic acid molecule (Fig. 1). The hetero-molecularar components of (I) are linked by O—H···N hydrogen bonds to form a one-dimensional chain (Table 1 & Fig. 2). These chains interact with each other via weak intermolecular C—H···O hydrogen bonds and C—H···π interactions. Within the asymmetric unit, the atoms C13, C16 and C17 act as hydrogen-bond donors (Table 1). The bond lengths and angles of these three hydrogen bonds are comparable with literature data (Bhogala et al., 2005; Wang et al., 2008). These hydrogen bonds, albeit rather weak, link the chains into two-dimensional double layers structure, which are further connected by weak intermolecular C—H···π interactions (Table 1) to generate a three-dimensional supramolecular structure (Fig. 3).

Experimental

4,4'-dipyridyl sulfide (18.84 mg, 0.1 mmol), isophthalic acid (16.51 mg, 0.1 mmol), and NaOH (8.13 mg, 0.2 mmol) were added to a H₂O solution (15 ml) in a Teflonlined stainless steel reactor. The mixture was heated at 473 K for 3 d, and then slowly cooled down to room temperature. Colorless crystals of the title compound were obtained.