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Acta Crystallogr Sect E Struct Rep Online. 2008 December 1; 64(Pt 12): o2279.
Published online 2008 November 8. doi:  10.1107/S1600536808035496
PMCID: PMC2960055

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

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 [triangle]); Wang et al. (2008 [triangle]). For C—H(...)π inter­actions, see: Fun & Kia (2008 [triangle]).

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Object name is e-64-o2279-scheme1.jpg

Experimental

Crystal data

  • C10H8N2S·C8H6O4
  • M r = 354.37
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2279-efi1.jpg
  • 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 [triangle]) 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 [triangle]); cell refinement: SAINT (Bruker, 1997 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

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.

Refinement

All hydrogen atoms were positioned geometrically and treated as riding, with C—H bonding lengths constrained to 0.93 (aromatic CH) and O—H bonding lengths constrained to 0.82 (OH), and with Uiso(H) = 1.2Ueq(C) and Uiso(H) = 1.5Ueq(O).

Figures

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.

Crystal data

C10H8N2S·C8H6O4Z = 2
Mr = 354.37F000 = 368
Triclinic, P1Dx = 1.403 Mg m3
a = 6.618 (6) ÅMo Kα radiation λ = 0.71073 Å
b = 8.200 (7) ÅCell parameters from 1298 reflections
c = 16.013 (13) Åθ = 2.9–21.2º
α = 88.808 (11)ºµ = 0.22 mm1
β = 79.340 (11)ºT = 291 (2) K
γ = 79.275 (11)ºBlock, colorless
V = 839.0 (12) Å30.47 × 0.30 × 0.11 mm

Data collection

Bruker SMART CCD area-detector diffractometer3084 independent reflections
Radiation source: fine-focus sealed tube1885 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.020
T = 291(2) Kθmax = 25.5º
[var phi] and ω scansθmin = 2.5º
Absorption correction: multi-scan(SADABS; Bruker, 1997)h = −8→7
Tmin = 0.905, Tmax = 0.977k = −9→9
6280 measured reflectionsl = −19→19

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.080H-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 reflectionsΔρmax = 1.05 e Å3
228 parametersΔρmin = −0.28 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

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

xyzUiso*/Ueq
S10.2928 (2)0.9132 (2)0.77591 (8)0.1000 (6)
O10.9948 (5)0.7101 (5)0.0723 (2)0.0868 (10)
H1D0.92030.73960.03710.130*
O20.7255 (6)0.5957 (5)0.1306 (2)0.0993 (12)
O30.7222 (6)0.3409 (5)0.4098 (2)0.0958 (12)
H3D0.67030.30730.45600.144*
O41.0069 (6)0.2941 (6)0.4653 (2)0.1133 (14)
N10.5677 (7)1.1790 (5)0.5430 (2)0.0733 (10)
N20.7476 (6)0.8077 (5)0.9602 (2)0.0777 (11)
C10.8967 (7)0.6270 (6)0.1321 (3)0.0716 (12)
C21.0110 (6)0.5765 (5)0.2024 (3)0.0636 (10)
C31.2038 (7)0.6166 (6)0.2056 (3)0.0724 (12)
H31.26940.67270.16050.087*
C41.2987 (7)0.5754 (6)0.2735 (3)0.0833 (14)
H41.42640.60580.27510.100*
C51.2062 (7)0.4887 (6)0.3400 (3)0.0772 (12)
H51.27210.45970.38610.093*
C61.0141 (6)0.4447 (5)0.3378 (3)0.0639 (10)
C70.9189 (6)0.4878 (5)0.2695 (2)0.0637 (10)
H70.79120.45740.26770.076*
C80.9164 (7)0.3505 (6)0.4099 (3)0.0734 (12)
C90.6939 (8)1.0749 (6)0.5857 (3)0.0761 (13)
H90.83761.05830.56610.091*
C100.6199 (8)0.9931 (6)0.6562 (3)0.0750 (12)
H100.71200.92080.68340.090*
C110.4099 (7)1.0177 (6)0.6868 (3)0.0691 (11)
C120.2817 (8)1.1212 (6)0.6439 (3)0.0782 (13)
H120.13771.13990.66310.094*
C130.3637 (8)1.1986 (6)0.5722 (3)0.0795 (13)
H130.27281.26730.54290.095*
C140.6067 (8)0.9811 (6)0.8561 (3)0.0833 (14)
H140.60561.07870.82540.100*
C150.7391 (8)0.9425 (6)0.9127 (3)0.0842 (15)
H150.82861.01500.91820.101*
C160.6162 (10)0.7091 (7)0.9505 (3)0.0917 (16)
H160.61690.61430.98340.110*
C170.4795 (8)0.7377 (6)0.8952 (3)0.0855 (15)
H170.38960.66440.89160.103*
C180.4760 (7)0.8763 (6)0.8449 (3)0.0716 (12)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0992 (10)0.1442 (14)0.0722 (9)−0.0626 (10)−0.0181 (7)0.0271 (8)
O10.091 (2)0.117 (3)0.0667 (19)−0.058 (2)−0.0187 (16)0.0361 (18)
O20.097 (2)0.150 (3)0.076 (2)−0.074 (2)−0.0345 (18)0.054 (2)
O30.093 (2)0.138 (3)0.074 (2)−0.057 (2)−0.0301 (18)0.053 (2)
O40.085 (2)0.152 (4)0.103 (3)−0.016 (2)−0.032 (2)0.068 (3)
N10.095 (3)0.077 (2)0.0527 (19)−0.028 (2)−0.0184 (19)0.0174 (17)
N20.099 (3)0.088 (3)0.056 (2)−0.045 (2)−0.0143 (19)0.0178 (19)
C10.074 (3)0.094 (3)0.056 (2)−0.043 (2)−0.010 (2)0.018 (2)
C20.062 (2)0.071 (3)0.059 (2)−0.021 (2)−0.0061 (19)0.0076 (19)
C30.069 (3)0.084 (3)0.070 (3)−0.035 (2)−0.007 (2)0.011 (2)
C40.063 (3)0.100 (4)0.092 (3)−0.031 (3)−0.013 (2)0.011 (3)
C50.069 (3)0.089 (3)0.074 (3)−0.010 (2)−0.020 (2)0.010 (2)
C60.061 (2)0.067 (3)0.063 (2)−0.0106 (19)−0.0114 (19)0.010 (2)
C70.061 (2)0.073 (3)0.060 (2)−0.023 (2)−0.0099 (19)0.012 (2)
C80.072 (3)0.082 (3)0.063 (3)−0.008 (2)−0.012 (2)0.017 (2)
C90.076 (3)0.091 (3)0.058 (2)−0.016 (2)−0.005 (2)0.016 (2)
C100.082 (3)0.080 (3)0.057 (2)−0.007 (2)−0.008 (2)0.019 (2)
C110.079 (3)0.076 (3)0.058 (2)−0.025 (2)−0.014 (2)0.003 (2)
C120.071 (3)0.092 (3)0.072 (3)−0.019 (2)−0.010 (2)−0.001 (2)
C130.084 (3)0.084 (3)0.077 (3)−0.017 (3)−0.033 (3)0.012 (3)
C140.107 (4)0.085 (3)0.072 (3)−0.043 (3)−0.027 (3)0.024 (2)
C150.108 (4)0.096 (3)0.063 (3)−0.056 (3)−0.017 (3)0.021 (2)
C160.136 (5)0.087 (3)0.068 (3)−0.058 (3)−0.024 (3)0.022 (2)
C170.111 (4)0.093 (3)0.068 (3)−0.059 (3)−0.019 (3)0.008 (3)
C180.083 (3)0.086 (3)0.049 (2)−0.033 (2)−0.002 (2)0.005 (2)

Geometric parameters (Å, °)

S1—C181.767 (5)C5—H50.9300
S1—C111.776 (5)C6—C71.369 (6)
O1—C11.308 (5)C6—C81.490 (6)
O1—H1D0.8200C7—H70.9300
O2—C11.212 (5)C9—C101.361 (6)
O3—C81.302 (6)C9—H90.9300
O3—H3D0.8200C10—C111.364 (6)
O4—C81.198 (5)C10—H100.9300
N1—C131.325 (6)C11—C121.356 (6)
N1—C91.347 (6)C12—C131.373 (7)
N2—C161.323 (6)C12—H120.9300
N2—C151.327 (6)C13—H130.9300
C1—C21.480 (6)C14—C181.364 (6)
C2—C31.385 (6)C14—C151.367 (7)
C2—C71.394 (5)C14—H140.9300
C3—C41.360 (6)C15—H150.9300
C3—H30.9300C16—C171.366 (7)
C4—C51.380 (6)C16—H160.9300
C4—H40.9300C17—C181.379 (6)
C5—C61.391 (6)C17—H170.9300
C18—S1—C11106.3 (2)N1—C9—H9118.6
C1—O1—H1D109.5C10—C9—H9118.6
C8—O3—H3D109.5C9—C10—C11119.6 (4)
C13—N1—C9117.0 (4)C9—C10—H10120.2
C16—N2—C15115.8 (4)C11—C10—H10120.2
O2—C1—O1122.8 (4)C12—C11—C10118.0 (4)
O2—C1—C2122.8 (4)C12—C11—S1117.9 (4)
O1—C1—C2114.3 (4)C10—C11—S1124.0 (4)
C3—C2—C7118.4 (4)C11—C12—C13120.2 (4)
C3—C2—C1122.9 (4)C11—C12—H12119.9
C7—C2—C1118.7 (4)C13—C12—H12119.9
C4—C3—C2121.1 (4)N1—C13—C12122.4 (4)
C4—C3—H3119.5N1—C13—H13118.8
C2—C3—H3119.5C12—C13—H13118.8
C3—C4—C5120.3 (4)C18—C14—C15119.8 (4)
C3—C4—H4119.9C18—C14—H14120.1
C5—C4—H4119.9C15—C14—H14120.1
C4—C5—C6119.8 (4)N2—C15—C14123.9 (4)
C4—C5—H5120.1N2—C15—H15118.1
C6—C5—H5120.1C14—C15—H15118.1
C7—C6—C5119.6 (4)N2—C16—C17124.2 (4)
C7—C6—C8121.2 (4)N2—C16—H16117.9
C5—C6—C8119.2 (4)C17—C16—H16117.9
C6—C7—C2120.9 (4)C16—C17—C18119.3 (4)
C6—C7—H7119.6C16—C17—H17120.3
C2—C7—H7119.6C18—C17—H17120.3
O4—C8—O3122.8 (4)C14—C18—C17116.9 (4)
O4—C8—C6122.5 (4)C14—C18—S1124.6 (4)
O3—C8—C6114.7 (4)C17—C18—S1118.4 (4)
N1—C9—C10122.8 (4)
O2—C1—C2—C3−178.0 (5)N1—C9—C10—C11−1.0 (8)
O1—C1—C2—C31.2 (7)C9—C10—C11—C121.5 (7)
O2—C1—C2—C70.6 (7)C9—C10—C11—S1177.7 (4)
O1—C1—C2—C7179.8 (4)C18—S1—C11—C12−152.0 (4)
C7—C2—C3—C4−2.1 (7)C18—S1—C11—C1031.8 (5)
C1—C2—C3—C4176.5 (4)C10—C11—C12—C13−0.4 (7)
C2—C3—C4—C51.6 (8)S1—C11—C12—C13−176.8 (4)
C3—C4—C5—C6−0.6 (8)C9—N1—C13—C121.9 (7)
C4—C5—C6—C70.1 (7)C11—C12—C13—N1−1.4 (8)
C4—C5—C6—C8179.8 (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—C2179.7 (4)C15—N2—C16—C170.9 (8)
C3—C2—C7—C61.6 (6)N2—C16—C17—C180.7 (9)
C1—C2—C7—C6−177.0 (4)C15—C14—C18—C172.7 (8)
C7—C6—C8—O4170.8 (5)C15—C14—C18—S1178.4 (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—O3168.3 (4)C11—S1—C18—C1434.9 (5)
C13—N1—C9—C10−0.7 (7)C11—S1—C18—C17−149.5 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C17—H17···O2i0.932.453.334 (6)159
C16—H16···O2ii0.932.583.180 (6)123
C13—H13···O4iii0.932.313.141 (6)148
C12—H12···Cg1iv0.932.983.570 (6)123
O3—H3D···N1v0.821.832.634 (5)164
O1—H1D···N2vi0.821.842.662 (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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SI2125).

References

  • Bhogala, B. R., Basavoju, S. & Nangia, A. (2005). Cryst. Growth Des.5, 1683–1686.
  • Bruker (1997). SMART, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Fun, H.-K. & Kia, R. (2008). Acta Cryst. E64, m1116–m1117. [PMC free article] [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Wang, Y.-T., Tang, G.-M., Zhang, Y.-C. & Wan, W.-Z. (2008). Acta Cryst. E64, o1753. [PMC free article] [PubMed]

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