1:1 Cocrystal of 2,5-di-4-pyridyl-1,3,4-oxadiazole and hydro­quinone

Wang, Y.-T.; Tang, G.-M.; Qin, D.-W.; Duan, H.-D.

doi:10.1107/S1600536805040018

1:1 Cocrystal of 2,5-di-4-pyridyl-1,3,4-oxadiazole and hydroquinone

Y.-T. Wang, G.-M. Tang, D.-W. Qin and H.-D. Duan

The title complex, 2,5-di-4-pyridyl-1,3,4-oxadiazole–hydroquinone (1/1), C₁₂H₈N₄O·C₆H₆O₂, crystallized from a solvent mixture of methanol and water. O—H

N hydrogen bonds link the molecules to give a chain structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805040018/ww6442sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805040018/ww6442Isup2.hkl Contains datablock I

CCDC reference: 296699

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.003 Å
R factor = 0.064
wR factor = 0.133
Data-to-parameter ratio = 10.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT031_ALERT_4_C Refined Extinction Parameter within Range ......       3.00 Sigma
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C6 H6 O2

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

Hydrogen bonding is important in the areas of crystal engineering, supramolecular chemistry, materials science and biological recognition (Desiraju, 1989; Jeffrey & Saenger, 1991; Holman et al., 2001). Recently, angular dipyridyl-donor basic compounds, such as 2,5-bis(4-pyridyl)-1,3,4-oxadiazole (bpo), have been used to produce a series of infinite/discrete coordination polymers/supramolecules with interesting structures and properties (Dong et al., 2003; Du et al., 2005). In our search to identify the properties of cocrystal materials of diol with linear/angular base components and to further understand the role of synthons in crystal engineering, we have prepared and determined the crystal structure of the acid–base cocrystal consisting of bpo and hydroquinone (Fig. 1).

A view of the title structure is shown in Fig. 1. The asymmetric unit consists of one bpo and one hydroquinone molecules. In the crystal structure, a one-dimensional chain is formed via O—H···N hydrogen bonds (Table 1 and Fig. 2).

Experimental top

A mixture of 2,5-bis(4-pyridyl)-1,3,4-oxadiazole (112 mg, 0.5 mmol) (Ren et al., 1995) and hydroquinone (55 mg, 0.5 mmol) was recrystallized from methanol and water in 70% yield (110 mg), from which a light-yellow needle-shaped crystal suitable for X-ray diffraction was selected. Analysis found: C 64.47, H 4.20, N 16.64%; requires: C 64.67, H 4.22, N 16.76%. IR (KBr, cm⁻¹): ν 2450, 1705, 1612, 1569, 1537, 1413, 1276, 1206, 1011, 836, 741, 723.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1999); software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. View of (I), showing displacement ellipsoids at the 30% probability level. [Please provide correct version of this figure]
	Fig. 2. Packing diagram (Spek, 2003), showing hydrogen bonds as dashed lines.

2,5-di-4-pyridyl-1,3,4-oxadiazole–hydroquinone (1/1) top

Crystal data top

C₁₂H₈N₄O·C₆H₆O₂	F(000) = 1392
M_r = 334.33	D_x = 1.425 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 250 reflections
a = 13.811 (7) Å	θ = 7.5–15°
b = 5.855 (2) Å	µ = 0.10 mm⁻¹
c = 38.550 (15) Å	T = 298 K
V = 3117 (2) Å³	Block, light yellow
Z = 8	0.30 × 0.30 × 0.20 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3067 independent reflections
Radiation source: fine-focus sealed tube	2489 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
ϕ and ω scans	θ_max = 26.0°, θ_min = 1.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −17→14
T_min = 0.971, T_max = 0.980	k = −7→7
15649 measured reflections	l = −47→45

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.064	All H-atom parameters refined
wR(F²) = 0.133	w = 1/[σ²(F_o²) + (0.0414P)² + 1.24P] where P = (F_o² + 2F_c²)/3
S = 1.20	(Δ/σ)_max = 0.001
3067 reflections	Δρ_max = 0.18 e Å⁻³
283 parameters	Δρ_min = −0.19 e Å⁻³
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0006 (2)

Crystal data top

C₁₂H₈N₄O·C₆H₆O₂	V = 3117 (2) Å³
M_r = 334.33	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 13.811 (7) Å	µ = 0.10 mm⁻¹
b = 5.855 (2) Å	T = 298 K
c = 38.550 (15) Å	0.30 × 0.30 × 0.20 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3067 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2489 reflections with I > 2σ(I)
T_min = 0.971, T_max = 0.980	R_int = 0.040
15649 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	0 restraints
wR(F²) = 0.133	All H-atom parameters refined
S = 1.20	Δρ_max = 0.18 e Å⁻³
3067 reflections	Δρ_min = −0.19 e Å⁻³
283 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 > 2σ(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	0.61549 (10)	0.0640 (2)	0.62018 (3)	0.0352 (4)
O2	0.58636 (16)	−0.4144 (4)	0.43791 (5)	0.0667 (6)
H2A	0.598 (2)	−0.310 (6)	0.4528 (8)	0.090 (12)*
O3	0.64782 (16)	−0.1372 (4)	0.30290 (5)	0.0641 (6)
H3A	0.636 (3)	−0.248 (7)	0.2877 (10)	0.138 (16)*
N1	0.61118 (15)	−0.0496 (4)	0.74922 (5)	0.0505 (6)
N2	0.67316 (14)	0.3979 (3)	0.63654 (5)	0.0418 (5)
N3	0.67319 (14)	0.3892 (3)	0.60024 (5)	0.0427 (5)
N4	0.61335 (14)	−0.1088 (4)	0.49237 (5)	0.0467 (5)
C1	0.6497 (2)	0.1561 (5)	0.74287 (6)	0.0506 (7)
C2	0.65888 (17)	0.2464 (4)	0.71016 (6)	0.0424 (6)
H2	0.6887 (17)	0.399 (4)	0.7071 (6)	0.052 (7)*
C3	0.62756 (15)	0.1189 (4)	0.68211 (5)	0.0357 (5)
C4	0.58750 (18)	−0.0932 (4)	0.68825 (6)	0.0449 (6)
H4	0.5684 (17)	−0.186 (4)	0.6709 (6)	0.055 (8)*
C5	0.58048 (19)	−0.1683 (5)	0.72196 (6)	0.0500 (7)
H5	0.5523 (18)	−0.315 (5)	0.7273 (6)	0.057 (7)*
C6	0.63957 (15)	0.2038 (4)	0.64682 (5)	0.0340 (5)
C7	0.63962 (15)	0.1908 (4)	0.59200 (5)	0.0347 (5)
C8	0.62817 (15)	0.0895 (4)	0.55778 (5)	0.0345 (5)
C9	0.66074 (17)	0.2023 (4)	0.52846 (6)	0.0414 (6)
H9	0.6917 (16)	0.345 (4)	0.5305 (6)	0.049 (7)*
C10	0.65182 (18)	0.0981 (5)	0.49675 (6)	0.0470 (6)
H10	0.6760 (17)	0.171 (4)	0.4757 (6)	0.056 (7)*
C11	0.58156 (18)	−0.2145 (5)	0.52080 (6)	0.0445 (6)
H11	0.5536 (16)	−0.363 (4)	0.5177 (6)	0.047 (7)*
C12	0.58769 (17)	−0.1248 (4)	0.55363 (6)	0.0405 (6)
H12	0.5658 (15)	−0.205 (4)	0.5724 (6)	0.040 (6)*
C13	0.60192 (17)	−0.3397 (4)	0.40463 (6)	0.0423 (6)
C14	0.64135 (19)	−0.1283 (4)	0.39694 (6)	0.0481 (6)
H14	0.6606 (17)	−0.027 (4)	0.4144 (6)	0.060 (8)*
C15	0.65631 (18)	−0.0637 (4)	0.36299 (7)	0.0469 (6)
H15	0.6845 (17)	0.073 (4)	0.3576 (6)	0.049 (7)*
C16	0.63140 (16)	−0.2082 (4)	0.33618 (6)	0.0409 (6)
C17	0.59244 (18)	−0.4188 (4)	0.34389 (6)	0.0459 (6)
H17	0.5774 (17)	−0.522 (4)	0.3254 (6)	0.057 (7)*
C18	0.57754 (19)	−0.4835 (5)	0.37778 (6)	0.0464 (6)
H18	0.5537 (18)	−0.622 (4)	0.3831 (6)	0.049 (7)*
H1	0.6713 (18)	0.245 (5)	0.7619 (7)	0.062 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0396 (9)	0.0364 (9)	0.0296 (8)	−0.0053 (7)	−0.0014 (6)	−0.0002 (7)
O2	0.1083 (17)	0.0578 (13)	0.0339 (10)	−0.0117 (12)	0.0074 (10)	−0.0024 (9)
O3	0.0932 (15)	0.0628 (13)	0.0365 (10)	−0.0079 (11)	0.0098 (10)	0.0050 (9)
N1	0.0574 (14)	0.0611 (14)	0.0332 (11)	0.0018 (11)	0.0067 (9)	−0.0012 (10)
N2	0.0490 (12)	0.0387 (11)	0.0377 (11)	−0.0067 (9)	0.0004 (9)	−0.0027 (9)
N3	0.0518 (12)	0.0378 (11)	0.0385 (11)	−0.0066 (9)	0.0004 (9)	0.0015 (9)
N4	0.0501 (12)	0.0555 (14)	0.0346 (11)	0.0052 (10)	−0.0057 (9)	−0.0029 (10)
C1	0.0578 (16)	0.0593 (17)	0.0348 (14)	−0.0011 (13)	0.0025 (12)	−0.0134 (12)
C2	0.0487 (14)	0.0415 (14)	0.0369 (13)	−0.0014 (12)	0.0030 (10)	−0.0091 (11)
C3	0.0317 (11)	0.0395 (13)	0.0358 (12)	0.0028 (10)	0.0022 (9)	−0.0026 (10)
C4	0.0508 (15)	0.0479 (16)	0.0360 (13)	−0.0067 (12)	0.0002 (11)	−0.0045 (11)
C5	0.0567 (17)	0.0490 (16)	0.0444 (15)	−0.0042 (13)	0.0096 (12)	0.0016 (12)
C6	0.0325 (12)	0.0359 (13)	0.0338 (12)	0.0016 (10)	−0.0021 (9)	−0.0053 (10)
C7	0.0321 (12)	0.0378 (13)	0.0343 (12)	−0.0015 (10)	0.0013 (9)	0.0058 (10)
C8	0.0321 (11)	0.0380 (13)	0.0335 (12)	0.0032 (10)	−0.0037 (9)	0.0036 (10)
C9	0.0445 (14)	0.0429 (14)	0.0367 (13)	−0.0030 (11)	−0.0020 (10)	0.0058 (11)
C10	0.0500 (15)	0.0576 (17)	0.0334 (13)	−0.0007 (13)	0.0007 (11)	0.0091 (12)
C11	0.0477 (15)	0.0413 (15)	0.0445 (14)	0.0005 (12)	−0.0073 (11)	−0.0014 (11)
C12	0.0478 (14)	0.0400 (14)	0.0338 (12)	−0.0037 (11)	−0.0009 (10)	0.0057 (10)
C13	0.0498 (14)	0.0431 (14)	0.0341 (12)	0.0006 (11)	0.0054 (10)	−0.0022 (10)
C14	0.0586 (16)	0.0461 (15)	0.0396 (14)	−0.0071 (12)	0.0039 (11)	−0.0129 (12)
C15	0.0544 (16)	0.0374 (14)	0.0490 (15)	−0.0085 (12)	0.0088 (12)	−0.0018 (12)
C16	0.0423 (13)	0.0459 (14)	0.0346 (12)	0.0032 (11)	0.0044 (10)	−0.0009 (10)
C17	0.0521 (15)	0.0508 (16)	0.0350 (13)	−0.0097 (12)	0.0008 (11)	−0.0118 (12)
C18	0.0553 (16)	0.0397 (15)	0.0442 (14)	−0.0065 (12)	0.0059 (12)	−0.0030 (11)

Geometric parameters (Å, º) top

O1—C6	1.355 (2)	C5—H5	0.97 (3)
O1—C7	1.357 (2)	C7—C8	1.455 (3)
O2—C13	1.372 (3)	C8—C12	1.383 (3)
O2—H2A	0.85 (3)	C8—C9	1.384 (3)
O3—C16	1.368 (3)	C9—C10	1.372 (3)
O3—H3A	0.89 (4)	C9—H9	0.94 (2)
N1—C5	1.329 (3)	C10—H10	0.98 (2)
N1—C1	1.339 (3)	C11—C12	1.373 (3)
N2—C6	1.290 (3)	C11—H11	0.96 (2)
N2—N3	1.400 (3)	C12—H12	0.91 (2)
N3—C7	1.291 (3)	C13—C18	1.376 (3)
N4—C11	1.333 (3)	C13—C14	1.384 (3)
N4—C10	1.333 (3)	C14—C15	1.378 (3)
C1—C2	1.373 (3)	C14—H14	0.93 (3)
C1—H1	0.95 (3)	C15—C16	1.379 (3)
C2—C3	1.383 (3)	C15—H15	0.92 (2)
C2—H2	0.99 (2)	C16—C17	1.378 (3)
C3—C4	1.380 (3)	C17—C18	1.376 (3)
C3—C6	1.458 (3)	C17—H17	0.96 (3)
C4—C5	1.375 (3)	C18—H18	0.90 (3)
C4—H4	0.90 (2)

C6—O1—C7	102.49 (17)	C10—C9—C8	119.1 (2)
C13—O2—H2A	112 (2)	C10—C9—H9	120.6 (14)
C16—O3—H3A	112 (3)	C8—C9—H9	120.2 (14)
C5—N1—C1	116.9 (2)	N4—C10—C9	123.5 (2)
C6—N2—N3	105.98 (17)	N4—C10—H10	115.3 (15)
C7—N3—N2	106.18 (18)	C9—C10—H10	121.1 (15)
C11—N4—C10	116.7 (2)	N4—C11—C12	124.1 (2)
N1—C1—C2	123.4 (2)	N4—C11—H11	116.9 (14)
N1—C1—H1	118.7 (16)	C12—C11—H11	119.1 (14)
C2—C1—H1	118.0 (16)	C11—C12—C8	118.6 (2)
C1—C2—C3	118.8 (2)	C11—C12—H12	120.9 (14)
C1—C2—H2	119.6 (14)	C8—C12—H12	120.5 (14)
C3—C2—H2	121.6 (14)	O2—C13—C18	118.0 (2)
C4—C3—C2	118.5 (2)	O2—C13—C14	123.1 (2)
C4—C3—C6	120.8 (2)	C18—C13—C14	118.8 (2)
C2—C3—C6	120.7 (2)	C15—C14—C13	120.5 (2)
C5—C4—C3	118.5 (2)	C15—C14—H14	117.8 (16)
C5—C4—H4	119.2 (16)	C13—C14—H14	121.6 (16)
C3—C4—H4	122.2 (16)	C14—C15—C16	120.4 (2)
N1—C5—C4	123.9 (3)	C14—C15—H15	121.4 (15)
N1—C5—H5	115.1 (14)	C16—C15—H15	118.2 (15)
C4—C5—H5	121.0 (15)	O3—C16—C17	122.6 (2)
N2—C6—O1	112.80 (18)	O3—C16—C15	118.4 (2)
N2—C6—C3	128.9 (2)	C17—C16—C15	119.0 (2)
O1—C6—C3	118.27 (19)	C18—C17—C16	120.6 (2)
N3—C7—O1	112.54 (18)	C18—C17—H17	120.1 (15)
N3—C7—C8	129.0 (2)	C16—C17—H17	119.3 (15)
O1—C7—C8	118.43 (19)	C13—C18—C17	120.6 (2)
C12—C8—C9	118.0 (2)	C13—C18—H18	117.9 (15)
C12—C8—C7	121.2 (2)	C17—C18—H18	121.4 (15)
C9—C8—C7	120.7 (2)

C6—N2—N3—C7	0.0 (2)	O1—C7—C8—C12	4.3 (3)
C5—N1—C1—C2	−0.3 (4)	N3—C7—C8—C9	4.3 (4)
N1—C1—C2—C3	−0.4 (4)	O1—C7—C8—C9	−173.44 (19)
C1—C2—C3—C4	0.6 (3)	C12—C8—C9—C10	−0.1 (3)
C1—C2—C3—C6	−177.4 (2)	C7—C8—C9—C10	177.7 (2)
C2—C3—C4—C5	0.0 (3)	C11—N4—C10—C9	0.8 (4)
C6—C3—C4—C5	178.0 (2)	C8—C9—C10—N4	−0.2 (4)
C1—N1—C5—C4	1.0 (4)	C10—N4—C11—C12	−1.1 (4)
C3—C4—C5—N1	−0.9 (4)	N4—C11—C12—C8	0.8 (4)
N3—N2—C6—O1	−0.8 (2)	C9—C8—C12—C11	−0.2 (3)
N3—N2—C6—C3	177.4 (2)	C7—C8—C12—C11	−178.0 (2)
C7—O1—C6—N2	1.2 (2)	O2—C13—C14—C15	179.2 (2)
C7—O1—C6—C3	−177.25 (18)	C18—C13—C14—C15	−0.3 (4)
C4—C3—C6—N2	178.2 (2)	C13—C14—C15—C16	0.6 (4)
C2—C3—C6—N2	−3.8 (4)	C14—C15—C16—O3	−179.8 (2)
C4—C3—C6—O1	−3.7 (3)	C14—C15—C16—C17	−0.8 (4)
C2—C3—C6—O1	174.29 (19)	O3—C16—C17—C18	179.7 (2)
N2—N3—C7—O1	0.8 (2)	C15—C16—C17—C18	0.7 (4)
N2—N3—C7—C8	−177.1 (2)	O2—C13—C18—C17	−179.3 (2)
C6—O1—C7—N3	−1.2 (2)	C14—C13—C18—C17	0.3 (4)
C6—O1—C7—C8	176.96 (18)	C16—C17—C18—C13	−0.5 (4)
N3—C7—C8—C12	−177.9 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···N4	0.85 (3)	1.94 (3)	2.784 (3)	170 (3)
O3—H3A···N1ⁱ	0.89 (4)	1.93 (4)	2.811 (3)	171 (4)

Symmetry code: (i) x, −y−1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₂H₈N₄O·C₆H₆O₂
M_r	334.33
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	298
a, b, c (Å)	13.811 (7), 5.855 (2), 38.550 (15)
V (Å³)	3117 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.30 × 0.30 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.971, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	15649, 3067, 2489
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.133, 1.20
No. of reflections	3067
No. of parameters	283
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.19

Computer programs: SMART (Bruker, 2001), SMART, SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Sheldrick, 1999), SHELXTL.