Di-4-pyridyl disulfide-isophthalic acid (1/1).

In the title 1:1 cocrystal, C(10)H(8)N(2)S(2)·C(8)H(6)O(4), the asymmetric unit contains an isophthalic acid mol-ecule and a 4,4'-dipyridyl disulfide mol-ecule. The two carboxyl groups of isophthalic acid inter-act with neighbouring 4,4'-dipyridyl disulfide mol-ecules through O-H⋯N hydrogen bonds, forming a one-dimensional zigzag chain. Neighbouring chains are linked to each other via π-π stacking inter-actions between the pyridyl rings of adjacent 4,4'-dipyridyl disulfide mol-ecules [centroid-centroid distance = 3.7346 (6) Å], resulting in a layered motif. The dihedral angle between pyridine rings of 84.13 (7)° and the C-S-S-C torsion angle of 91.95 (1)° confirm the gauche conformation of 4,4'-dipyridyl disulfide.

Related literature

For ligands with two 4-pyridyl donors, see: Biradha et al. (2006 ▶); Sun et al. (2006 ▶); He et al. (2008 ▶); Suen et al. (2005 ▶). For related structures, see: Ranjbar et al. (2007 ▶).

Experimental

Crystal data

C10H8N2S2·C8H6O4

M = 386.43

Monoclinic,

a = 5.9616 (12) Å

b = 10.024 (2) Å

c = 29.797 (6) Å

β = 93.71 (3)°

V = 1776.9 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.33 mm−1

T = 295 K

0.29 × 0.20 × 0.11 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.920, T max = 0.964

16923 measured reflections

4039 independent reflections

2330 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.135

S = 1.08

4039 reflections

235 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.41 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); 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: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809013397/pv2150sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809013397/pv2150Isup2.hkl

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

C10H8N2S2·C8H6O4	F(000) = 800
Mr = 386.43	Dx = 1.445 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 16923 reflections
a = 5.9616 (12) Å	θ = 3.4–27.4°
b = 10.024 (2) Å	µ = 0.33 mm−1
c = 29.797 (6) Å	T = 295 K
β = 93.71 (3)°	Platelet, colorless
V = 1776.9 (6) Å3	0.29 × 0.20 × 0.11 mm
Z = 4

Rigaku R-AXIS RAPID diffractometer	4039 independent reflections
Radiation source: fine-focus sealed tube	2330 reflections with I > 2σ(I)
graphite	Rint = 0.048
Detector resolution: 0 pixels mm-1	θmax = 27.4°, θmin = 3.4°
ω scans	h = −7→7
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −12→12
Tmin = 0.920, Tmax = 0.964	l = −38→38
16923 measured reflections

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0469P)2 + 0.8478P] where P = (Fo2 + 2Fc2)/3
4039 reflections	(Δ/σ)max < 0.001
235 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.41 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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
C1	0.1566 (4)	0.1783 (3)	0.32831 (8)	0.0472 (6)
C2	0.1371 (5)	0.0516 (3)	0.31039 (10)	0.0570 (7)
H2A	0.2419	−0.0142	0.3187	0.068*
C3	−0.0411 (5)	0.0247 (3)	0.27995 (10)	0.0616 (8)
H3A	−0.0545	−0.0611	0.2682	0.074*
N1	−0.1955 (4)	0.1147 (2)	0.26642 (7)	0.0541 (6)
C4	−0.1742 (5)	0.2369 (3)	0.28378 (9)	0.0542 (7)
H4A	−0.2806	0.3011	0.2748	0.065*
C5	−0.0019 (5)	0.2723 (3)	0.31427 (9)	0.0526 (7)
H5A	0.0079	0.3589	0.3254	0.063*
S1	0.36292 (14)	0.23223 (8)	0.36981 (3)	0.0629 (2)
S2	0.59614 (12)	0.08517 (9)	0.37425 (3)	0.0664 (3)
C6	0.5151 (4)	−0.0234 (3)	0.41697 (8)	0.0467 (6)
C7	0.6649 (4)	−0.1247 (3)	0.42909 (9)	0.0543 (7)
H7A	0.7977	−0.1335	0.4146	0.065*
C8	0.6162 (5)	−0.2124 (3)	0.46265 (10)	0.0588 (8)
H8A	0.7195	−0.2791	0.4708	0.071*
N2	0.4262 (4)	−0.2055 (3)	0.48407 (7)	0.0571 (6)
C9	0.2814 (5)	−0.1082 (3)	0.47191 (9)	0.0558 (7)
H9A	0.1483	−0.1031	0.4865	0.067*
C10	0.3170 (4)	−0.0152 (3)	0.43917 (9)	0.0520 (7)
H10A	0.2119	0.0513	0.4321	0.062*
O1	0.6473 (5)	0.7527 (3)	0.28620 (9)	0.0996 (9)
O2	0.5074 (3)	0.5519 (2)	0.29642 (6)	0.0634 (6)
H2C	0.3967	0.5742	0.2715	0.095*
C11	0.6474 (5)	0.6489 (3)	0.30626 (9)	0.0528 (7)
C12	0.8127 (4)	0.6179 (3)	0.34480 (8)	0.0452 (6)
C13	1.0212 (5)	0.6802 (3)	0.34736 (9)	0.0541 (7)
H13A	1.0553	0.7426	0.3257	0.065*
C14	1.1780 (5)	0.6495 (3)	0.38191 (10)	0.0603 (8)
H14A	1.3179	0.6909	0.3833	0.072*
C15	1.1292 (4)	0.5580 (3)	0.41451 (9)	0.0574 (8)
H15A	1.2368	0.5368	0.4374	0.069*
C16	0.9196 (4)	0.4977 (3)	0.41308 (8)	0.0467 (6)
C17	0.7617 (4)	0.5277 (3)	0.37792 (8)	0.0451 (6)
H17A	0.6214	0.4868	0.3767	0.054*
C18	0.8684 (5)	0.3991 (3)	0.44862 (9)	0.0566 (7)
O3	1.0115 (4)	0.3410 (3)	0.47123 (9)	0.0996 (9)
O4	0.6531 (3)	0.3815 (2)	0.45246 (7)	0.0695 (6)
H4C	0.6275	0.3313	0.4726	0.104*

	U11	U22	U33	U12	U13	U23
C1	0.0550 (16)	0.0416 (15)	0.0445 (14)	−0.0047 (12)	0.0007 (12)	0.0048 (12)
C2	0.0646 (18)	0.0438 (17)	0.0606 (17)	0.0055 (14)	−0.0107 (14)	−0.0019 (13)
C3	0.078 (2)	0.0459 (17)	0.0589 (17)	−0.0006 (16)	−0.0134 (16)	−0.0092 (14)
N1	0.0640 (15)	0.0536 (15)	0.0433 (12)	−0.0002 (12)	−0.0078 (11)	0.0003 (11)
C4	0.0624 (17)	0.0485 (17)	0.0509 (15)	0.0066 (14)	−0.0027 (14)	0.0038 (13)
C5	0.0681 (18)	0.0391 (15)	0.0502 (15)	0.0009 (14)	−0.0005 (14)	−0.0019 (12)
S1	0.0717 (5)	0.0503 (5)	0.0638 (5)	−0.0141 (4)	−0.0174 (4)	0.0058 (4)
S2	0.0482 (4)	0.0838 (6)	0.0672 (5)	−0.0068 (4)	0.0036 (3)	0.0218 (4)
C6	0.0386 (13)	0.0557 (17)	0.0447 (13)	−0.0022 (12)	−0.0055 (11)	−0.0001 (12)
C7	0.0433 (15)	0.0660 (19)	0.0527 (16)	0.0059 (14)	−0.0033 (12)	−0.0024 (14)
C8	0.0587 (17)	0.0601 (19)	0.0552 (16)	0.0083 (15)	−0.0144 (14)	0.0001 (15)
N2	0.0612 (15)	0.0606 (16)	0.0477 (13)	−0.0051 (13)	−0.0106 (11)	0.0067 (11)
C9	0.0489 (15)	0.067 (2)	0.0510 (15)	−0.0048 (15)	0.0008 (13)	0.0040 (14)
C10	0.0434 (14)	0.0571 (18)	0.0551 (15)	0.0022 (13)	−0.0007 (12)	0.0064 (14)
O1	0.118 (2)	0.0680 (17)	0.1053 (19)	−0.0274 (15)	−0.0499 (16)	0.0421 (15)
O2	0.0698 (13)	0.0577 (13)	0.0589 (12)	−0.0097 (11)	−0.0244 (10)	0.0090 (10)
C11	0.0612 (17)	0.0465 (17)	0.0495 (15)	−0.0013 (14)	−0.0059 (13)	0.0043 (13)
C12	0.0509 (15)	0.0405 (15)	0.0435 (13)	0.0004 (12)	−0.0026 (12)	−0.0027 (11)
C13	0.0570 (17)	0.0544 (18)	0.0507 (15)	−0.0046 (14)	0.0011 (13)	0.0000 (13)
C14	0.0458 (15)	0.071 (2)	0.0634 (18)	−0.0101 (15)	−0.0001 (14)	−0.0047 (16)
C15	0.0455 (15)	0.072 (2)	0.0526 (16)	0.0031 (15)	−0.0103 (13)	−0.0050 (15)
C16	0.0452 (14)	0.0530 (17)	0.0408 (13)	0.0033 (12)	−0.0054 (11)	−0.0026 (12)
C17	0.0446 (14)	0.0447 (15)	0.0449 (13)	0.0002 (12)	−0.0044 (11)	−0.0011 (12)
C18	0.0541 (16)	0.069 (2)	0.0454 (15)	0.0018 (15)	−0.0095 (13)	0.0063 (14)
O3	0.0644 (14)	0.135 (2)	0.0961 (18)	0.0153 (16)	−0.0159 (13)	0.0616 (18)
O4	0.0580 (12)	0.0864 (16)	0.0624 (12)	−0.0072 (11)	−0.0107 (10)	0.0307 (11)

C1—C5	1.380 (4)	C9—H9A	0.9300
C1—C2	1.380 (4)	C10—H10A	0.9300
C1—S1	1.771 (3)	O1—C11	1.200 (3)
C2—C3	1.378 (4)	O2—C11	1.302 (3)
C2—H2A	0.9300	O2—H2C	0.9857
C3—N1	1.333 (4)	C11—C12	1.497 (4)
C3—H3A	0.9300	C12—C17	1.387 (4)
N1—C4	1.333 (4)	C12—C13	1.388 (4)
C4—C5	1.373 (4)	C13—C14	1.379 (4)
C4—H4A	0.9300	C13—H13A	0.9300
C5—H5A	0.9300	C14—C15	1.381 (4)
S1—S2	2.0248 (13)	C14—H14A	0.9300
S2—C6	1.766 (3)	C15—C16	1.386 (4)
C6—C7	1.385 (4)	C15—H15A	0.9300
C6—C10	1.393 (3)	C16—C17	1.395 (3)
C7—C8	1.376 (4)	C16—C18	1.495 (4)
C7—H7A	0.9300	C17—H17A	0.9300
C8—N2	1.338 (4)	C18—O3	1.203 (3)
C8—H8A	0.9300	C18—O4	1.308 (3)
N2—C9	1.337 (4)	O4—H4C	0.8043
C9—C10	1.376 (4)
C5—C1—C2	118.2 (3)	C10—C9—H9A	118.0
C5—C1—S1	115.7 (2)	C9—C10—C6	118.1 (3)
C2—C1—S1	126.0 (2)	C9—C10—H10A	120.9
C3—C2—C1	118.5 (3)	C6—C10—H10A	120.9
C3—C2—H2A	120.8	C11—O2—H2C	112.9
C1—C2—H2A	120.8	O1—C11—O2	123.7 (3)
N1—C3—C2	123.7 (3)	O1—C11—C12	122.7 (3)
N1—C3—H3A	118.2	O2—C11—C12	113.5 (2)
C2—C3—H3A	118.2	C17—C12—C13	119.4 (2)
C3—N1—C4	117.3 (2)	C17—C12—C11	121.2 (2)
N1—C4—C5	122.8 (3)	C13—C12—C11	119.5 (2)
N1—C4—H4A	118.6	C14—C13—C12	120.1 (3)
C5—C4—H4A	118.6	C14—C13—H13A	119.9
C4—C5—C1	119.5 (3)	C12—C13—H13A	119.9
C4—C5—H5A	120.2	C13—C14—C15	120.6 (3)
C1—C5—H5A	120.2	C13—C14—H14A	119.7
C1—S1—S2	105.44 (10)	C15—C14—H14A	119.7
C6—S2—S1	106.08 (10)	C14—C15—C16	119.9 (3)
C7—C6—C10	118.1 (3)	C14—C15—H15A	120.0
C7—C6—S2	116.0 (2)	C16—C15—H15A	120.0
C10—C6—S2	125.9 (2)	C15—C16—C17	119.5 (3)
C8—C7—C6	119.7 (3)	C15—C16—C18	119.4 (2)
C8—C7—H7A	120.2	C17—C16—C18	121.0 (2)
C6—C7—H7A	120.2	C12—C17—C16	120.4 (2)
N2—C8—C7	122.6 (3)	C12—C17—H17A	119.8
N2—C8—H8A	118.7	C16—C17—H17A	119.8
C7—C8—H8A	118.7	O3—C18—O4	123.4 (3)
C9—N2—C8	117.4 (2)	O3—C18—C16	123.2 (3)
N2—C9—C10	124.0 (3)	O4—C18—C16	113.4 (2)
N2—C9—H9A	118.0	C18—O4—H4C	112.6

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2C···N1i	0.99	1.64	2.629 (3)	175
O4—H4C···N2ii	0.81	1.85	2.651 (3)	176

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2C⋯N1i	0.99	1.64	2.629 (3)	175
O4—H4C⋯N2ii	0.81	1.85	2.651 (3)	176

Symmetry codes: (i) ; (ii) .