supplementary materials


Acta Cryst. (2008). E64, o2279    [ doi:10.1107/S1600536808035496 ]

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

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

Abstract top

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...[pi] interactions to generate a three-dimensional supramolecular structure.

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.

Refinement top

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).

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
[Figure 1] 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.
[Figure 2] Fig. 2. A view of the one-dimensional hydrogen-bond chain motif.
[Figure 3] 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·C8H6O4Z = 2
Mr = 354.37F(000) = 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 = 2.9–21.2°
α = 88.808 (11)°µ = 0.22 mm1
β = 79.340 (11)°T = 291 K
γ = 79.275 (11)°Block, colorless
V = 839.0 (12) Å30.47 × 0.30 × 0.11 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
3084 independent reflections
Radiation source: fine-focus sealed tube1885 reflections with I > 2σ(I)
graphiteRint = 0.020
φ and ω scansθmax = 25.5°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
h = 87
Tmin = 0.905, Tmax = 0.977k = 99
6280 measured reflectionsl = 1919
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.080Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.269H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.1354P)2 + 0.4871P]
where P = (Fo2 + 2Fc2)/3
3084 reflections(Δ/σ)max < 0.001
228 parametersΔρmax = 1.05 e Å3
0 restraintsΔρmin = 0.28 e Å3
Crystal data top
C10H8N2S·C8H6O4γ = 79.275 (11)°
Mr = 354.37V = 839.0 (12) Å3
Triclinic, P1Z = 2
a = 6.618 (6) ÅMo Kα radiation
b = 8.200 (7) ŵ = 0.22 mm1
c = 16.013 (13) ÅT = 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)
Tmin = 0.905, Tmax = 0.977Rint = 0.020
6280 measured reflectionsθmax = 25.5°
Refinement top
R[F2 > 2σ(F2)] = 0.080H-atom parameters constrained
wR(F2) = 0.269Δρmax = 1.05 e Å3
S = 1.08Δρmin = 0.28 e Å3
3084 reflectionsAbsolute structure: ?
228 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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) top
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, °) top
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—C3178.0 (5)N1—C9—C10—C111.0 (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—C12152.0 (4)
C7—C2—C3—C42.1 (7)C18—S1—C11—C1031.8 (5)
C1—C2—C3—C4176.5 (4)C10—C11—C12—C130.4 (7)
C2—C3—C4—C51.6 (8)S1—C11—C12—C13176.8 (4)
C3—C4—C5—C60.6 (8)C9—N1—C13—C121.9 (7)
C4—C5—C6—C70.1 (7)C11—C12—C13—N11.4 (8)
C4—C5—C6—C8179.8 (4)C16—N2—C15—C140.5 (8)
C5—C6—C7—C20.6 (7)C18—C14—C15—N21.3 (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—C6177.0 (4)C15—C14—C18—C172.7 (8)
C7—C6—C8—O4170.8 (5)C15—C14—C18—S1178.4 (4)
C5—C6—C8—O48.8 (7)C16—C17—C18—C142.4 (8)
C7—C6—C8—O312.1 (6)C16—C17—C18—S1178.4 (4)
C5—C6—C8—O3168.3 (4)C11—S1—C18—C1434.9 (5)
C13—N1—C9—C100.7 (7)C11—S1—C18—C17149.5 (4)
Hydrogen-bond geometry (Å, °) top
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.
Table 1
Hydrogen-bond geometry (Å, °)
top
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.
Acknowledgements top

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references
References top

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.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Wang, Y.-T., Tang, G.-M., Zhang, Y.-C. & Wan, W.-Z. (2008). Acta Cryst. E64, o1753.