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

Qin, J.-H.; Li, X.-D.; Wang, J.-G.

doi:10.1107/S1600536808035496

organic compounds

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Volume 64| Part 12| December 2008| Page o2279

doi:10.1107/S1600536808035496

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

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

^aCollege of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang 471022, People's Republic of China
^*Correspondence e-mail: jh_q128105@126.com

(Received 21 October 2008; accepted 30 October 2008; online 8 November 2008)

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, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.080
wR(F²) = 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

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
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x, y, z+1; (iii) x-1, y+1, z; (iv) -x+1, -y+2, -z+1; (v) x, y-1, z; (vi) x, y, z-1. Cg1 is the centroid of the C2–C7 isophthalic acid ring.

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.

Supporting information

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

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

checkCIF report

Comment top

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).

Related literature top

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 top

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.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the hetero-molecular components of the title compound with the atom labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A view of the one-dimensional hydrogen-bond chain motif.
	Fig. 3. A view of the C—H···O hydrogen bond and the C—H···π interactions in the crystal structure of the title compound.

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

Crystal data top

C₁₀H₈N₂S·C₈H₆O₄	Z = 2
M_r = 354.37	F(000) = 368
Triclinic, P1	D_x = 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 = 2.9–21.2°
α = 88.808 (11)°	µ = 0.22 mm⁻¹
β = 79.340 (11)°	T = 291 K
γ = 79.275 (11)°	Block, colorless
V = 839.0 (12) Å³	0.47 × 0.30 × 0.11 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3084 independent reflections
Radiation source: fine-focus sealed tube	1885 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ϕ and ω scans	θ_max = 25.5°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −8→7
T_min = 0.905, T_max = 0.977	k = −9→9
6280 measured reflections	l = −19→19

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)] = 0.080	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.269	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.1354P)² + 0.4871P] where P = (F_o² + 2F_c²)/3
3084 reflections	(Δ/σ)_max < 0.001
228 parameters	Δρ_max = 1.05 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₀H₈N₂S·C₈H₆O₄	γ = 79.275 (11)°
M_r = 354.37	V = 839.0 (12) Å³
Triclinic, P1	Z = 2
a = 6.618 (6) Å	Mo Kα radiation
b = 8.200 (7) Å	µ = 0.22 mm⁻¹
c = 16.013 (13) Å	T = 291 K
α = 88.808 (11)°	0.47 × 0.30 × 0.11 mm
β = 79.340 (11)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3084 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1997)	1885 reflections with I > 2σ(I)
T_min = 0.905, T_max = 0.977	R_int = 0.020
6280 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.080	0 restraints
wR(F²) = 0.269	H-atom parameters constrained
S = 1.08	Δρ_max = 1.05 e Å⁻³
3084 reflections	Δρ_min = −0.28 e Å⁻³
228 parameters

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

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y, z+1; (iii) x−1, y+1, z; (iv) −x+1, −y+2, −z+1; (v) x, y−1, z; (vi) x, y, z−1.

Experimental details

Crystal data
Chemical formula	C₁₀H₈N₂S·C₈H₆O₄
M_r	354.37
Crystal system, space group	Triclinic, P1
Temperature (K)	291
a, b, c (Å)	6.618 (6), 8.200 (7), 16.013 (13)
α, β, γ (°)	88.808 (11), 79.340 (11), 79.275 (11)
V (Å³)	839.0 (12)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.47 × 0.30 × 0.11

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1997)
T_min, T_max	0.905, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	6280, 3084, 1885
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.080, 0.269, 1.08
No. of reflections	3084
No. of parameters	228
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.05, −0.28

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···O2ⁱ	0.93	2.45	3.334 (6)	159.4
C16—H16···O2ⁱⁱ	0.93	2.58	3.180 (6)	122.6
C13—H13···O4ⁱⁱⁱ	0.93	2.31	3.141 (6)	148.3
C12—H12···Cg1^iv	0.93	2.98	3.570 (6)	123
O3—H3D···N1^v	0.82	1.83	2.634 (5)	164.4
O1—H1D···N2^vi	0.82	1.84	2.662 (5)	178.6

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y, z+1; (iii) x−1, y+1, z; (iv) −x+1, −y+2, −z+1; (v) x, y−1, z; (vi) x, y, z−1.

Acknowledgements

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

References

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