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Acta Cryst. (2008). E64, o1754    [ doi:10.1107/S1600536808025555 ]

Naphthalene-2,3-diol-imidazole (1/1)

Y.-T. Wang, G.-M. Tang and W.-Z. Wan

Abstract top

In the title cocrystal, C10H8O2·C3H4N2, intermolecular O-H...O and N-H...O hydrogen bonds connect the naphthalene-2,3-diol and imidazole molecules into a two-dimensional supramolecular framework.

Comment top

During past decade, the field of molecular co-crystals have received considerable attention, for example, the design, construction, properties and the definition of molecular co-crystals, partly because co-crystallization reactions offer unique opportunities for examining the balance between and structural influence of intermolecular interactions. Recently, a lot of co-crystals containing some organic acids and bases, have been successfully synthesized and characterized by our research group. Especially, co-crystals containing naphthalene-2,7-diol with some organic bases have been prepared and reported (Wang & Tang, 2006; Wang, Tang & Ng, 2006; Wang, Tang & Wan, 2006). A series of supramolecular structures of self-assembly with different motifs have been obtained. There are a few co-crystals about naphthalene-2,3-diol (ndo) as organic acid; some interesting structures have been generated through supramolecular self-assemblies (Fritchie & Johnston, 1975; Wells, et al., 1974). To study a series of co-crystals containing ndo and to further explore its properties, we have selected the structure of the co-crystal, (I), of ndo and imidazole.

A view of the title structure is shown in Fig. 1. The asymmetric unit consists of one independent ndo molecule and one independent molecule of imidazole. In the crystal structure of the title compound, intermolecular O—H···O and N—H···O hydrogen bonds connect naphthalene-2,3-diol molecules and imidazole molecules into a linear ribbon motif, which are further extended to two-dimensional supramolecular framwork through N—H···O hydrogen bonds (Table 1, Fig. 2).

Related literature top

For other cocrystals of naphthalene-2,3-diol, see: Fritchie & Johnston (1975); Wang & Tang (2006); Wang, Tang & Ng (2006); Wang, Tang & Wan (2006); Wells et al. (1974).

Experimental top

A mixture of naphthalene-2,3-diol (80 mg, 0.5 mmol) and imidazole (34 mg, 0.5 mmol) was recrystallized from methanol (5 ml) and water (1 ml) (yield: 102 mg, 90%), from which a yellow needle suitable for x-ray diffraction was selected. Analysis found (%): C 68.21; H, 5.33; N, 12.21; requires (%): C, 68.41; H, 5.30; N, 12.27.

Refinement top

All H atoms were located in a difference Fourier map. Carbon-bound hydrogen atoms were positioned geometrically (C—H = 0.93 A °), and were included in the refinement in the riding-model approximation, with Uiso(H) = 1.2Ueq(C). Oxygen- and nitrogen-bound hydrogen atoms were restrained and refined independently, with isotropic displacement parameters, giving final O—H and N—H distances in the range 0.895 (5)–0.911 (9), 0.897 (10) A °, respectively.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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 drawing of (I), with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. Packing diagram of (I); hydrogen bonds are shown by dashed lines.
Naphthalene-2,3-diol–imidazole (1/1) top
Crystal data top
C10H8O2·C3H4N2F000 = 960
Mr = 228.25Dx = 1.255 Mg m−3
Orthorhombic, PbcaMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 5055 reflections
a = 12.0003 (17) Åθ = 2.3–26.3º
b = 7.7862 (11) ŵ = 0.09 mm−1
c = 25.863 (4) ÅT = 296 (2) K
V = 2416.6 (6) Å3Column, yellow
Z = 80.30 × 0.30 × 0.20 mm
Data collection top
Bruker SMART
diffractometer		2142 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.031
Monochromator: graphiteθmax = 27.6º
T = 296(2) Kθmin = 1.6º
φ and ω scansh = −13→15
Absorption correction: Nonek = −10→9
18637 measured reflectionsl = −33→33
2777 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.125  w = 1/[σ2(Fo2) + (0.0675P)2 + 0.2922P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
2777 reflectionsΔρmax = 0.16 e Å−3
166 parametersΔρmin = −0.20 e Å−3
3 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
C10H8O2·C3H4N2V = 2416.6 (6) Å3
Mr = 228.25Z = 8
Orthorhombic, PbcaMo Kα
a = 12.0003 (17) ŵ = 0.09 mm−1
b = 7.7862 (11) ÅT = 296 (2) K
c = 25.863 (4) Å0.30 × 0.30 × 0.20 mm
Data collection top
Bruker SMART
diffractometer		2777 independent reflections
Absorption correction: None2142 reflections with I > 2σ(I)
18637 measured reflectionsRint = 0.031
Refinement top
R[F2 > 2σ(F2)] = 0.0413 restraints
wR(F2) = 0.125H atoms treated by a mixture of
independent and constrained refinement
S = 1.04Δρmax = 0.16 e Å−3
2777 reflectionsΔρmin = −0.20 e Å−3
166 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.75477 (8)0.63170 (13)0.59205 (4)0.0517 (3)
H1B0.8003 (12)0.7228 (17)0.5918 (7)0.074 (5)*
O20.60386 (7)0.39458 (12)0.57667 (4)0.0519 (3)
H2A0.5427 (12)0.333 (2)0.5673 (8)0.094 (6)*
C10.63552 (11)0.78573 (16)0.65109 (5)0.0438 (3)
H1A0.69090.86650.65750.053*
C20.65645 (10)0.65273 (15)0.61825 (4)0.0396 (3)
C30.57423 (10)0.52524 (15)0.60887 (4)0.0404 (3)
C40.47199 (11)0.54089 (16)0.63144 (5)0.0455 (3)
H40.41760.45870.62470.055*
C50.44700 (11)0.67966 (17)0.66483 (5)0.0443 (3)
C60.34112 (12)0.6975 (2)0.68858 (6)0.0570 (4)
H60.28490.61940.68090.068*
C70.32087 (14)0.8271 (2)0.72241 (6)0.0671 (5)
H70.25140.83590.73810.081*
C80.40329 (16)0.9469 (2)0.73374 (6)0.0705 (5)
H80.38861.03450.75720.085*
C90.50538 (14)0.9372 (2)0.71078 (5)0.0594 (4)
H90.55921.01950.71830.071*
C100.53038 (11)0.80258 (16)0.67555 (4)0.0435 (3)
C110.40496 (13)0.1697 (2)0.50288 (5)0.0577 (4)
H110.42950.23190.47440.069*
C120.31524 (16)−0.0138 (3)0.54918 (7)0.0804 (5)
H120.2671−0.10070.55970.096*
C130.38620 (14)0.0743 (2)0.57906 (6)0.0673 (4)
H130.39550.05830.61440.081*
N10.44264 (9)0.19072 (14)0.54994 (4)0.0504 (3)
N20.32741 (12)0.0486 (2)0.50092 (5)0.0682 (4)
H2B0.2928 (17)0.018 (3)0.4716 (6)0.113 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0449 (5)0.0484 (6)0.0619 (6)−0.0061 (4)0.0087 (4)−0.0098 (4)
O20.0416 (5)0.0462 (5)0.0678 (6)0.0014 (4)−0.0028 (4)−0.0219 (4)
C10.0484 (7)0.0386 (7)0.0445 (6)−0.0042 (5)−0.0078 (5)−0.0028 (5)
C20.0384 (6)0.0395 (7)0.0409 (6)0.0014 (5)−0.0018 (5)0.0006 (5)
C30.0417 (7)0.0356 (6)0.0439 (6)0.0030 (5)−0.0058 (5)−0.0050 (5)
C40.0405 (7)0.0401 (7)0.0561 (7)−0.0026 (5)−0.0010 (5)−0.0056 (6)
C50.0454 (7)0.0442 (7)0.0432 (6)0.0066 (6)−0.0012 (5)0.0003 (5)
C60.0497 (8)0.0621 (9)0.0593 (8)0.0064 (7)0.0059 (6)−0.0005 (7)
C70.0620 (10)0.0788 (11)0.0605 (9)0.0202 (9)0.0108 (7)−0.0058 (8)
C80.0773 (12)0.0754 (11)0.0588 (9)0.0247 (9)−0.0010 (8)−0.0242 (8)
C90.0659 (10)0.0562 (9)0.0560 (8)0.0088 (7)−0.0103 (7)−0.0176 (7)
C100.0505 (7)0.0406 (7)0.0394 (6)0.0072 (5)−0.0069 (5)−0.0025 (5)
C110.0628 (9)0.0592 (9)0.0511 (7)0.0000 (7)−0.0112 (7)−0.0014 (6)
C120.0776 (12)0.0805 (12)0.0830 (12)−0.0316 (10)0.0031 (9)−0.0055 (10)
C130.0733 (11)0.0780 (11)0.0506 (8)−0.0107 (9)−0.0028 (7)−0.0013 (7)
N10.0504 (6)0.0479 (6)0.0528 (6)0.0003 (5)−0.0107 (5)−0.0094 (5)
N20.0618 (8)0.0771 (10)0.0656 (8)−0.0072 (7)−0.0184 (7)−0.0204 (7)
Geometric parameters (Å, °) top
O1—C21.3705 (15)C7—C81.390 (3)
O1—H1B0.895 (9)C7—H70.9300
O2—C31.3620 (14)C8—C91.363 (2)
O2—H2A0.911 (9)C8—H80.9300
C1—C21.3627 (17)C9—C101.4207 (18)
C1—C101.4176 (18)C9—H90.9300
C1—H1A0.9300C11—N11.3089 (17)
C2—C31.4204 (17)C11—N21.326 (2)
C3—C41.3642 (17)C11—H110.9300
C4—C51.4154 (18)C12—C131.339 (2)
C4—H40.9300C12—N21.347 (2)
C5—C101.4120 (19)C12—H120.9300
C5—C61.4180 (18)C13—N11.359 (2)
C6—C71.358 (2)C13—H130.9300
C6—H60.9300N2—H2B0.897 (10)
C2—O1—H1B115.7 (11)C9—C8—C7120.68 (14)
C3—O2—H2A110.3 (13)C9—C8—H8119.7
C2—C1—C10120.83 (11)C7—C8—H8119.7
C2—C1—H1A119.6C8—C9—C10120.65 (15)
C10—C1—H1A119.6C8—C9—H9119.7
C1—C2—O1123.90 (11)C10—C9—H9119.7
C1—C2—C3120.63 (11)C5—C10—C1118.71 (11)
O1—C2—C3115.47 (10)C5—C10—C9118.44 (13)
O2—C3—C4124.27 (11)C1—C10—C9122.85 (13)
O2—C3—C2116.43 (11)N1—C11—N2111.53 (14)
C4—C3—C2119.29 (11)N1—C11—H11124.2
C3—C4—C5121.32 (12)N2—C11—H11124.2
C3—C4—H4119.3C13—C12—N2106.33 (15)
C5—C4—H4119.3C13—C12—H12126.8
C10—C5—C4119.15 (12)N2—C12—H12126.8
C10—C5—C6118.92 (12)C12—C13—N1109.81 (15)
C4—C5—C6121.92 (13)C12—C13—H13125.1
C7—C6—C5120.81 (15)N1—C13—H13125.1
C7—C6—H6119.6C11—N1—C13105.05 (12)
C5—C6—H6119.6C11—N2—C12107.28 (12)
C6—C7—C8120.46 (15)C11—N2—H2B123.1 (15)
C6—C7—H7119.8C12—N2—H2B129.6 (15)
C8—C7—H7119.8
C10—C1—C2—O1177.81 (11)C7—C8—C9—C10−1.2 (2)
C10—C1—C2—C3−1.71 (18)C4—C5—C10—C12.02 (18)
C1—C2—C3—O2−178.13 (11)C6—C5—C10—C1−179.01 (11)
O1—C2—C3—O22.31 (16)C4—C5—C10—C9−177.49 (12)
C1—C2—C3—C42.72 (18)C6—C5—C10—C91.48 (18)
O1—C2—C3—C4−176.84 (11)C2—C1—C10—C5−0.67 (18)
O2—C3—C4—C5179.59 (12)C2—C1—C10—C9178.82 (12)
C2—C3—C4—C5−1.33 (19)C8—C9—C10—C50.2 (2)
C3—C4—C5—C10−1.02 (19)C8—C9—C10—C1−179.33 (14)
C3—C4—C5—C6−179.96 (13)N2—C12—C13—N1−0.1 (2)
C10—C5—C6—C7−2.1 (2)N2—C11—N1—C130.76 (18)
C4—C5—C6—C7176.80 (14)C12—C13—N1—C11−0.39 (19)
C5—C6—C7—C81.1 (2)N1—C11—N2—C12−0.8 (2)
C6—C7—C8—C90.6 (3)C13—C12—N2—C110.6 (2)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1B···O2i0.92 (2)1.78 (2)2.6877 (14)166 (2)
O2—H2A···N11.03 (2)1.57 (2)2.5947 (15)170 (2)
N2—H2B···O1ii0.89 (2)2.09 (3)2.9185 (19)156 (2)
Symmetry codes: (i) x+2, −y−1/2, z−1/2; (ii) −x−1, y+1/2, −z+3/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1B···O2i0.92 (2)1.78 (2)2.6877 (14)166 (2)
O2—H2A···N11.03 (2)1.57 (2)2.5947 (15)170 (2)
N2—H2B···O1ii0.89 (2)2.09 (3)2.9185 (19)156 (2)
Symmetry codes: (i) x+2, −y−1/2, z−1/2; (ii) −x−1, y+1/2, −z+3/2.
Acknowledgements top

This work was supported by the Starting Fund of Shandong Institute of Light Industry (to Y-TW).

references
References top

Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Fritchie, C. J. & Johnston, R. M. (1975). Acta Cryst. B31, 454–461.

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

Wang, Y.-T. & Tang, G.-M. (2006). Acta Cryst. E62, o3833–o3834.

Wang, Y.-T., Tang, G.-M. & Ng, S. W. (2006). Acta Cryst. E62, o4429–o4430.

Wang, Y.-T., Tang, G.-M. & Wan, W.-Z. (2006). Acta Cryst. E62, o3396–o3397.

Wells, J. L., Trus, B. L., Johnston, R. M., Marsh, R. E. & Fritchie, C. J. (1974). Acta Cryst. B30, 1127–1134.