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

In the heteromolecular title structure, C(10)H(8)N(2)S·C(8)H(6)O(4), the two components are linked by O-H⋯N hydrogen bonds to form a one-dimensional chain. These chains are further inter-connected by weak inter-molecular C-H⋯O hydrogen bonds and weak C-H⋯π inter-actions to generate a three-dimensional supra-molecular 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 = 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

Δρmax = 1.05 e Å−3

Δρmin = −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.

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

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

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

C10H8N2S·C8H6O4	Z = 2
Mr = 354.37	F000 = 368
Triclinic, P1	Dx = 1.403 Mg m−3
a = 6.618 (6) Å	Mo Kα radiation λ = 0.71073 Å
b = 8.200 (7) Å	Cell parameters from 1298 reflections
c = 16.013 (13) Å	θ = 2.9–21.2º
α = 88.808 (11)º	µ = 0.22 mm−1
β = 79.340 (11)º	T = 291 (2) K
γ = 79.275 (11)º	Block, colorless
V = 839.0 (12) Å3	0.47 × 0.30 × 0.11 mm

Bruker SMART CCD area-detector diffractometer	3084 independent reflections
Radiation source: fine-focus sealed tube	1885 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.020
T = 291(2) K	θmax = 25.5º
φ and ω scans	θmin = 2.5º
Absorption correction: multi-scan(SADABS; Bruker, 1997)	h = −8→7
Tmin = 0.905, Tmax = 0.977	k = −9→9
6280 measured reflections	l = −19→19

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.080	H-atom parameters constrained
wR(F2) = 0.269	w = 1/[σ2(Fo2) + (0.1354P)2 + 0.4871P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
3084 reflections	Δρmax = 1.05 e Å−3
228 parameters	Δρmin = −0.28 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

	x	y	z	Uiso*/Ueq
S1	0.2928 (2)	0.9132 (2)	0.77591 (8)	0.1000 (6)
O1	0.9948 (5)	0.7101 (5)	0.0723 (2)	0.0868 (10)
H1D	0.9203	0.7396	0.0371	0.130*
O2	0.7255 (6)	0.5957 (5)	0.1306 (2)	0.0993 (12)
O3	0.7222 (6)	0.3409 (5)	0.4098 (2)	0.0958 (12)
H3D	0.6703	0.3073	0.4560	0.144*
O4	1.0069 (6)	0.2941 (6)	0.4653 (2)	0.1133 (14)
N1	0.5677 (7)	1.1790 (5)	0.5430 (2)	0.0733 (10)
N2	0.7476 (6)	0.8077 (5)	0.9602 (2)	0.0777 (11)
C1	0.8967 (7)	0.6270 (6)	0.1321 (3)	0.0716 (12)
C2	1.0110 (6)	0.5765 (5)	0.2024 (3)	0.0636 (10)
C3	1.2038 (7)	0.6166 (6)	0.2056 (3)	0.0724 (12)
H3	1.2694	0.6727	0.1605	0.087*
C4	1.2987 (7)	0.5754 (6)	0.2735 (3)	0.0833 (14)
H4	1.4264	0.6058	0.2751	0.100*
C5	1.2062 (7)	0.4887 (6)	0.3400 (3)	0.0772 (12)
H5	1.2721	0.4597	0.3861	0.093*
C6	1.0141 (6)	0.4447 (5)	0.3378 (3)	0.0639 (10)
C7	0.9189 (6)	0.4878 (5)	0.2695 (2)	0.0637 (10)
H7	0.7912	0.4574	0.2677	0.076*
C8	0.9164 (7)	0.3505 (6)	0.4099 (3)	0.0734 (12)
C9	0.6939 (8)	1.0749 (6)	0.5857 (3)	0.0761 (13)
H9	0.8376	1.0583	0.5661	0.091*
C10	0.6199 (8)	0.9931 (6)	0.6562 (3)	0.0750 (12)
H10	0.7120	0.9208	0.6834	0.090*
C11	0.4099 (7)	1.0177 (6)	0.6868 (3)	0.0691 (11)
C12	0.2817 (8)	1.1212 (6)	0.6439 (3)	0.0782 (13)
H12	0.1377	1.1399	0.6631	0.094*
C13	0.3637 (8)	1.1986 (6)	0.5722 (3)	0.0795 (13)
H13	0.2728	1.2673	0.5429	0.095*
C14	0.6067 (8)	0.9811 (6)	0.8561 (3)	0.0833 (14)
H14	0.6056	1.0787	0.8254	0.100*
C15	0.7391 (8)	0.9425 (6)	0.9127 (3)	0.0842 (15)
H15	0.8286	1.0150	0.9182	0.101*
C16	0.6162 (10)	0.7091 (7)	0.9505 (3)	0.0917 (16)
H16	0.6169	0.6143	0.9834	0.110*
C17	0.4795 (8)	0.7377 (6)	0.8952 (3)	0.0855 (15)
H17	0.3896	0.6644	0.8916	0.103*
C18	0.4760 (7)	0.8763 (6)	0.8449 (3)	0.0716 (12)

	U11	U22	U33	U12	U13	U23
S1	0.0992 (10)	0.1442 (14)	0.0722 (9)	−0.0626 (10)	−0.0181 (7)	0.0271 (8)
O1	0.091 (2)	0.117 (3)	0.0667 (19)	−0.058 (2)	−0.0187 (16)	0.0361 (18)
O2	0.097 (2)	0.150 (3)	0.076 (2)	−0.074 (2)	−0.0345 (18)	0.054 (2)
O3	0.093 (2)	0.138 (3)	0.074 (2)	−0.057 (2)	−0.0301 (18)	0.053 (2)
O4	0.085 (2)	0.152 (4)	0.103 (3)	−0.016 (2)	−0.032 (2)	0.068 (3)
N1	0.095 (3)	0.077 (2)	0.0527 (19)	−0.028 (2)	−0.0184 (19)	0.0174 (17)
N2	0.099 (3)	0.088 (3)	0.056 (2)	−0.045 (2)	−0.0143 (19)	0.0178 (19)
C1	0.074 (3)	0.094 (3)	0.056 (2)	−0.043 (2)	−0.010 (2)	0.018 (2)
C2	0.062 (2)	0.071 (3)	0.059 (2)	−0.021 (2)	−0.0061 (19)	0.0076 (19)
C3	0.069 (3)	0.084 (3)	0.070 (3)	−0.035 (2)	−0.007 (2)	0.011 (2)
C4	0.063 (3)	0.100 (4)	0.092 (3)	−0.031 (3)	−0.013 (2)	0.011 (3)
C5	0.069 (3)	0.089 (3)	0.074 (3)	−0.010 (2)	−0.020 (2)	0.010 (2)
C6	0.061 (2)	0.067 (3)	0.063 (2)	−0.0106 (19)	−0.0114 (19)	0.010 (2)
C7	0.061 (2)	0.073 (3)	0.060 (2)	−0.023 (2)	−0.0099 (19)	0.012 (2)
C8	0.072 (3)	0.082 (3)	0.063 (3)	−0.008 (2)	−0.012 (2)	0.017 (2)
C9	0.076 (3)	0.091 (3)	0.058 (2)	−0.016 (2)	−0.005 (2)	0.016 (2)
C10	0.082 (3)	0.080 (3)	0.057 (2)	−0.007 (2)	−0.008 (2)	0.019 (2)
C11	0.079 (3)	0.076 (3)	0.058 (2)	−0.025 (2)	−0.014 (2)	0.003 (2)
C12	0.071 (3)	0.092 (3)	0.072 (3)	−0.019 (2)	−0.010 (2)	−0.001 (2)
C13	0.084 (3)	0.084 (3)	0.077 (3)	−0.017 (3)	−0.033 (3)	0.012 (3)
C14	0.107 (4)	0.085 (3)	0.072 (3)	−0.043 (3)	−0.027 (3)	0.024 (2)
C15	0.108 (4)	0.096 (3)	0.063 (3)	−0.056 (3)	−0.017 (3)	0.021 (2)
C16	0.136 (5)	0.087 (3)	0.068 (3)	−0.058 (3)	−0.024 (3)	0.022 (2)
C17	0.111 (4)	0.093 (3)	0.068 (3)	−0.059 (3)	−0.019 (3)	0.008 (3)
C18	0.083 (3)	0.086 (3)	0.049 (2)	−0.033 (2)	−0.002 (2)	0.005 (2)

S1—C18	1.767 (5)	C5—H5	0.9300
S1—C11	1.776 (5)	C6—C7	1.369 (6)
O1—C1	1.308 (5)	C6—C8	1.490 (6)
O1—H1D	0.8200	C7—H7	0.9300
O2—C1	1.212 (5)	C9—C10	1.361 (6)
O3—C8	1.302 (6)	C9—H9	0.9300
O3—H3D	0.8200	C10—C11	1.364 (6)
O4—C8	1.198 (5)	C10—H10	0.9300
N1—C13	1.325 (6)	C11—C12	1.356 (6)
N1—C9	1.347 (6)	C12—C13	1.373 (7)
N2—C16	1.323 (6)	C12—H12	0.9300
N2—C15	1.327 (6)	C13—H13	0.9300
C1—C2	1.480 (6)	C14—C18	1.364 (6)
C2—C3	1.385 (6)	C14—C15	1.367 (7)
C2—C7	1.394 (5)	C14—H14	0.9300
C3—C4	1.360 (6)	C15—H15	0.9300
C3—H3	0.9300	C16—C17	1.366 (7)
C4—C5	1.380 (6)	C16—H16	0.9300
C4—H4	0.9300	C17—C18	1.379 (6)
C5—C6	1.391 (6)	C17—H17	0.9300
C18—S1—C11	106.3 (2)	N1—C9—H9	118.6
C1—O1—H1D	109.5	C10—C9—H9	118.6
C8—O3—H3D	109.5	C9—C10—C11	119.6 (4)
C13—N1—C9	117.0 (4)	C9—C10—H10	120.2
C16—N2—C15	115.8 (4)	C11—C10—H10	120.2
O2—C1—O1	122.8 (4)	C12—C11—C10	118.0 (4)
O2—C1—C2	122.8 (4)	C12—C11—S1	117.9 (4)
O1—C1—C2	114.3 (4)	C10—C11—S1	124.0 (4)
C3—C2—C7	118.4 (4)	C11—C12—C13	120.2 (4)
C3—C2—C1	122.9 (4)	C11—C12—H12	119.9
C7—C2—C1	118.7 (4)	C13—C12—H12	119.9
C4—C3—C2	121.1 (4)	N1—C13—C12	122.4 (4)
C4—C3—H3	119.5	N1—C13—H13	118.8
C2—C3—H3	119.5	C12—C13—H13	118.8
C3—C4—C5	120.3 (4)	C18—C14—C15	119.8 (4)
C3—C4—H4	119.9	C18—C14—H14	120.1
C5—C4—H4	119.9	C15—C14—H14	120.1
C4—C5—C6	119.8 (4)	N2—C15—C14	123.9 (4)
C4—C5—H5	120.1	N2—C15—H15	118.1
C6—C5—H5	120.1	C14—C15—H15	118.1
C7—C6—C5	119.6 (4)	N2—C16—C17	124.2 (4)
C7—C6—C8	121.2 (4)	N2—C16—H16	117.9
C5—C6—C8	119.2 (4)	C17—C16—H16	117.9
C6—C7—C2	120.9 (4)	C16—C17—C18	119.3 (4)
C6—C7—H7	119.6	C16—C17—H17	120.3
C2—C7—H7	119.6	C18—C17—H17	120.3
O4—C8—O3	122.8 (4)	C14—C18—C17	116.9 (4)
O4—C8—C6	122.5 (4)	C14—C18—S1	124.6 (4)
O3—C8—C6	114.7 (4)	C17—C18—S1	118.4 (4)
N1—C9—C10	122.8 (4)
O2—C1—C2—C3	−178.0 (5)	N1—C9—C10—C11	−1.0 (8)
O1—C1—C2—C3	1.2 (7)	C9—C10—C11—C12	1.5 (7)
O2—C1—C2—C7	0.6 (7)	C9—C10—C11—S1	177.7 (4)
O1—C1—C2—C7	179.8 (4)	C18—S1—C11—C12	−152.0 (4)
C7—C2—C3—C4	−2.1 (7)	C18—S1—C11—C10	31.8 (5)
C1—C2—C3—C4	176.5 (4)	C10—C11—C12—C13	−0.4 (7)
C2—C3—C4—C5	1.6 (8)	S1—C11—C12—C13	−176.8 (4)
C3—C4—C5—C6	−0.6 (8)	C9—N1—C13—C12	1.9 (7)
C4—C5—C6—C7	0.1 (7)	C11—C12—C13—N1	−1.4 (8)
C4—C5—C6—C8	179.8 (4)	C16—N2—C15—C14	−0.5 (8)
C5—C6—C7—C2	−0.6 (7)	C18—C14—C15—N2	−1.3 (8)
C8—C6—C7—C2	179.7 (4)	C15—N2—C16—C17	0.9 (8)
C3—C2—C7—C6	1.6 (6)	N2—C16—C17—C18	0.7 (9)
C1—C2—C7—C6	−177.0 (4)	C15—C14—C18—C17	2.7 (8)
C7—C6—C8—O4	170.8 (5)	C15—C14—C18—S1	178.4 (4)
C5—C6—C8—O4	−8.8 (7)	C16—C17—C18—C14	−2.4 (8)
C7—C6—C8—O3	−12.1 (6)	C16—C17—C18—S1	−178.4 (4)
C5—C6—C8—O3	168.3 (4)	C11—S1—C18—C14	34.9 (5)
C13—N1—C9—C10	−0.7 (7)	C11—S1—C18—C17	−149.5 (4)

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···Cg1iv	0.93	2.98	3.570 (6)	123
O3—H3D···N1v	0.82	1.83	2.634 (5)	164
O1—H1D···N2vi	0.82	1.84	2.662 (5)	179

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⋯Cg1iv	0.93	2.98	3.570 (6)	123
O3—H3D⋯N1v	0.82	1.83	2.634 (5)	164
O1—H1D⋯N2vi	0.82	1.84	2.662 (5)	179

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