Naphthalene-2,3-diol–imidazole (1/1)

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

doi:10.1107/S1600536808025555

organic compounds

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Volume 64| Part 9| September 2008| Page o1754

doi:10.1107/S1600536808025555

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Naphthalene-2,3-diol–imidazole (1/1)

Yong-Tao Wang,^a ^* Gui-Mei Tang ^a and Wen-Zhu Wan ^a

^aDepartment of Chemical Engineering, Shandong Institute of Light Industry, Jinan, Shandong 250353, People's Republic of China
^*Correspondence e-mail: ceswyt@sohu.com

(Received 5 August 2008; accepted 8 August 2008; online 13 August 2008)

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.

Related literature

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

Crystal data

C₁₀H₈O₂·C₃H₄N₂
M_r = 228.25
Orthorhombic, P b c a
a = 12.0003 (17) Å
b = 7.7862 (11) Å
c = 25.863 (4) Å
V = 2416.6 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 (2) K
0.30 × 0.30 × 0.20 mm

Data collection

Bruker SMART diffractometer
Absorption correction: none
18637 measured reflections
2777 independent reflections
2142 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.125
S = 1.04
2777 reflections
166 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1B⋯O2ⁱ	0.92 (2)	1.78 (2)	2.6877 (14)	166 (2)
O2—H2A⋯N1	1.03 (2)	1.57 (2)	2.5947 (15)	170 (2)
N2—H2B⋯O1ⁱⁱ	0.89 (2)	2.09 (3)	2.9185 (19)	156 (2)
Symmetry codes: (i) $[x+2, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x-1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: SMART; cell refinement: SAINT (Bruker, 2001 ); 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 global, I. DOI: 10.1107/S1600536808025555/ng2483sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808025555/ng2483Isup2.hkl

checkCIF report

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.

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

	Fig. 1. A drawing of (I), with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	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·C₃H₄N₂	F(000) = 960
M_r = 228.25	D_x = 1.255 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 5055 reflections
a = 12.0003 (17) Å	θ = 2.3–26.3°
b = 7.7862 (11) Å	µ = 0.09 mm⁻¹
c = 25.863 (4) Å	T = 296 K
V = 2416.6 (6) Å³	Column, yellow
Z = 8	0.30 × 0.30 × 0.20 mm

Data collection top

Bruker SMART diffractometer	2142 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.031
Graphite monochromator	θ_max = 27.6°, θ_min = 1.6°
ϕ and ω scans	h = −13→15
18637 measured reflections	k = −10→9
2777 independent reflections	l = −33→33

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0675P)² + 0.2922P] where P = (F_o² + 2F_c²)/3
2777 reflections	(Δ/σ)_max < 0.001
166 parameters	Δρ_max = 0.16 e Å⁻³
3 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₀H₈O₂·C₃H₄N₂	V = 2416.6 (6) Å³
M_r = 228.25	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 12.0003 (17) Å	µ = 0.09 mm⁻¹
b = 7.7862 (11) Å	T = 296 K
c = 25.863 (4) Å	0.30 × 0.30 × 0.20 mm

Data collection top

Bruker SMART diffractometer	2142 reflections with I > 2σ(I)
18637 measured reflections	R_int = 0.031
2777 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	3 restraints
wR(F²) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.16 e Å⁻³
2777 reflections	Δρ_min = −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

	x	y	z	U_iso*/U_eq
O1	0.75477 (8)	0.63170 (13)	0.59205 (4)	0.0517 (3)
H1B	0.8003 (12)	0.7228 (17)	0.5918 (7)	0.074 (5)*
O2	0.60386 (7)	0.39458 (12)	0.57667 (4)	0.0519 (3)
H2A	0.5427 (12)	0.333 (2)	0.5673 (8)	0.094 (6)*
C1	0.63552 (11)	0.78573 (16)	0.65109 (5)	0.0438 (3)
H1A	0.6909	0.8665	0.6575	0.053*
C2	0.65645 (10)	0.65273 (15)	0.61825 (4)	0.0396 (3)
C3	0.57423 (10)	0.52524 (15)	0.60887 (4)	0.0404 (3)
C4	0.47199 (11)	0.54089 (16)	0.63144 (5)	0.0455 (3)
H4	0.4176	0.4587	0.6247	0.055*
C5	0.44700 (11)	0.67966 (17)	0.66483 (5)	0.0443 (3)
C6	0.34112 (12)	0.6975 (2)	0.68858 (6)	0.0570 (4)
H6	0.2849	0.6194	0.6809	0.068*
C7	0.32087 (14)	0.8271 (2)	0.72241 (6)	0.0671 (5)
H7	0.2514	0.8359	0.7381	0.081*
C8	0.40329 (16)	0.9469 (2)	0.73374 (6)	0.0705 (5)
H8	0.3886	1.0345	0.7572	0.085*
C9	0.50538 (14)	0.9372 (2)	0.71078 (5)	0.0594 (4)
H9	0.5592	1.0195	0.7183	0.071*
C10	0.53038 (11)	0.80258 (16)	0.67555 (4)	0.0435 (3)
C11	0.40496 (13)	0.1697 (2)	0.50288 (5)	0.0577 (4)
H11	0.4295	0.2319	0.4744	0.069*
C12	0.31524 (16)	−0.0138 (3)	0.54918 (7)	0.0804 (5)
H12	0.2671	−0.1007	0.5597	0.096*
C13	0.38620 (14)	0.0743 (2)	0.57906 (6)	0.0673 (4)
H13	0.3955	0.0583	0.6144	0.081*
N1	0.44264 (9)	0.19072 (14)	0.54994 (4)	0.0504 (3)
N2	0.32741 (12)	0.0486 (2)	0.50092 (5)	0.0682 (4)
H2B	0.2928 (17)	0.018 (3)	0.4716 (6)	0.113 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0449 (5)	0.0484 (6)	0.0619 (6)	−0.0061 (4)	0.0087 (4)	−0.0098 (4)
O2	0.0416 (5)	0.0462 (5)	0.0678 (6)	0.0014 (4)	−0.0028 (4)	−0.0219 (4)
C1	0.0484 (7)	0.0386 (7)	0.0445 (6)	−0.0042 (5)	−0.0078 (5)	−0.0028 (5)
C2	0.0384 (6)	0.0395 (7)	0.0409 (6)	0.0014 (5)	−0.0018 (5)	0.0006 (5)
C3	0.0417 (7)	0.0356 (6)	0.0439 (6)	0.0030 (5)	−0.0058 (5)	−0.0050 (5)
C4	0.0405 (7)	0.0401 (7)	0.0561 (7)	−0.0026 (5)	−0.0010 (5)	−0.0056 (6)
C5	0.0454 (7)	0.0442 (7)	0.0432 (6)	0.0066 (6)	−0.0012 (5)	0.0003 (5)
C6	0.0497 (8)	0.0621 (9)	0.0593 (8)	0.0064 (7)	0.0059 (6)	−0.0005 (7)
C7	0.0620 (10)	0.0788 (11)	0.0605 (9)	0.0202 (9)	0.0108 (7)	−0.0058 (8)
C8	0.0773 (12)	0.0754 (11)	0.0588 (9)	0.0247 (9)	−0.0010 (8)	−0.0242 (8)
C9	0.0659 (10)	0.0562 (9)	0.0560 (8)	0.0088 (7)	−0.0103 (7)	−0.0176 (7)
C10	0.0505 (7)	0.0406 (7)	0.0394 (6)	0.0072 (5)	−0.0069 (5)	−0.0025 (5)
C11	0.0628 (9)	0.0592 (9)	0.0511 (7)	0.0000 (7)	−0.0112 (7)	−0.0014 (6)
C12	0.0776 (12)	0.0805 (12)	0.0830 (12)	−0.0316 (10)	0.0031 (9)	−0.0055 (10)
C13	0.0733 (11)	0.0780 (11)	0.0506 (8)	−0.0107 (9)	−0.0028 (7)	−0.0013 (7)
N1	0.0504 (6)	0.0479 (6)	0.0528 (6)	0.0003 (5)	−0.0107 (5)	−0.0094 (5)
N2	0.0618 (8)	0.0771 (10)	0.0656 (8)	−0.0072 (7)	−0.0184 (7)	−0.0204 (7)

Geometric parameters (Å, º) top

O1—C2	1.3705 (15)	C7—C8	1.390 (3)
O1—H1B	0.895 (9)	C7—H7	0.9300
O2—C3	1.3620 (14)	C8—C9	1.363 (2)
O2—H2A	0.911 (9)	C8—H8	0.9300
C1—C2	1.3627 (17)	C9—C10	1.4207 (18)
C1—C10	1.4176 (18)	C9—H9	0.9300
C1—H1A	0.9300	C11—N1	1.3089 (17)
C2—C3	1.4204 (17)	C11—N2	1.326 (2)
C3—C4	1.3642 (17)	C11—H11	0.9300
C4—C5	1.4154 (18)	C12—C13	1.339 (2)
C4—H4	0.9300	C12—N2	1.347 (2)
C5—C10	1.4120 (19)	C12—H12	0.9300
C5—C6	1.4180 (18)	C13—N1	1.359 (2)
C6—C7	1.358 (2)	C13—H13	0.9300
C6—H6	0.9300	N2—H2B	0.897 (10)

C2—O1—H1B	115.7 (11)	C9—C8—C7	120.68 (14)
C3—O2—H2A	110.3 (13)	C9—C8—H8	119.7
C2—C1—C10	120.83 (11)	C7—C8—H8	119.7
C2—C1—H1A	119.6	C8—C9—C10	120.65 (15)
C10—C1—H1A	119.6	C8—C9—H9	119.7
C1—C2—O1	123.90 (11)	C10—C9—H9	119.7
C1—C2—C3	120.63 (11)	C5—C10—C1	118.71 (11)
O1—C2—C3	115.47 (10)	C5—C10—C9	118.44 (13)
O2—C3—C4	124.27 (11)	C1—C10—C9	122.85 (13)
O2—C3—C2	116.43 (11)	N1—C11—N2	111.53 (14)
C4—C3—C2	119.29 (11)	N1—C11—H11	124.2
C3—C4—C5	121.32 (12)	N2—C11—H11	124.2
C3—C4—H4	119.3	C13—C12—N2	106.33 (15)
C5—C4—H4	119.3	C13—C12—H12	126.8
C10—C5—C4	119.15 (12)	N2—C12—H12	126.8
C10—C5—C6	118.92 (12)	C12—C13—N1	109.81 (15)
C4—C5—C6	121.92 (13)	C12—C13—H13	125.1
C7—C6—C5	120.81 (15)	N1—C13—H13	125.1
C7—C6—H6	119.6	C11—N1—C13	105.05 (12)
C5—C6—H6	119.6	C11—N2—C12	107.28 (12)
C6—C7—C8	120.46 (15)	C11—N2—H2B	123.1 (15)
C6—C7—H7	119.8	C12—N2—H2B	129.6 (15)
C8—C7—H7	119.8

C10—C1—C2—O1	177.81 (11)	C7—C8—C9—C10	−1.2 (2)
C10—C1—C2—C3	−1.71 (18)	C4—C5—C10—C1	2.02 (18)
C1—C2—C3—O2	−178.13 (11)	C6—C5—C10—C1	−179.01 (11)
O1—C2—C3—O2	2.31 (16)	C4—C5—C10—C9	−177.49 (12)
C1—C2—C3—C4	2.72 (18)	C6—C5—C10—C9	1.48 (18)
O1—C2—C3—C4	−176.84 (11)	C2—C1—C10—C5	−0.67 (18)
O2—C3—C4—C5	179.59 (12)	C2—C1—C10—C9	178.82 (12)
C2—C3—C4—C5	−1.33 (19)	C8—C9—C10—C5	0.2 (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—C13	0.76 (18)
C4—C5—C6—C7	176.80 (14)	C12—C13—N1—C11	−0.39 (19)
C5—C6—C7—C8	1.1 (2)	N1—C11—N2—C12	−0.8 (2)
C6—C7—C8—C9	0.6 (3)	C13—C12—N2—C11	0.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1B···O2ⁱ	0.92 (2)	1.78 (2)	2.6877 (14)	166 (2)
O2—H2A···N1	1.03 (2)	1.57 (2)	2.5947 (15)	170 (2)
N2—H2B···O1ⁱⁱ	0.89 (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.

Experimental details

Crystal data
Chemical formula	C₁₀H₈O₂·C₃H₄N₂
M_r	228.25
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	296
a, b, c (Å)	12.0003 (17), 7.7862 (11), 25.863 (4)
V (Å³)	2416.6 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.30 × 0.20

Data collection
Diffractometer	Bruker SMART diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	18637, 2777, 2142
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.125, 1.04
No. of reflections	2777
No. of parameters	166
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.20

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), 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
O1—H1B···O2ⁱ	0.92 (2)	1.78 (2)	2.6877 (14)	166 (2)
O2—H2A···N1	1.03 (2)	1.57 (2)	2.5947 (15)	170 (2)
N2—H2B···O1ⁱⁱ	0.89 (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

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

References

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