Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805040018/ww6442sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805040018/ww6442Isup2.hkl |
CCDC reference: 296699
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.
All H atoms were located in a difference Fourier map and refined independently with isotropic displacement parameters.
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.
C12H8N4O·C6H6O2 | F(000) = 1392 |
Mr = 334.33 | Dx = 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 |
Bruker SMART CCD area-detector diffractometer | 3067 independent reflections |
Radiation source: fine-focus sealed tube | 2489 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.040 |
ϕ and ω scans | θmax = 26.0°, θmin = 1.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −17→14 |
Tmin = 0.971, Tmax = 0.980 | k = −7→7 |
15649 measured reflections | l = −47→45 |
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(Fo2) + (0.0414P)2 + 1.24P] where P = (Fo2 + 2Fc2)/3 |
S = 1.20 | (Δ/σ)max = 0.001 |
3067 reflections | Δρmax = 0.18 e Å−3 |
283 parameters | Δρmin = −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) |
C12H8N4O·C6H6O2 | V = 3117 (2) Å3 |
Mr = 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 |
Bruker SMART CCD area-detector diffractometer | 3067 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 2489 reflections with I > 2σ(I) |
Tmin = 0.971, Tmax = 0.980 | Rint = 0.040 |
15649 measured reflections |
R[F2 > 2σ(F2)] = 0.064 | 0 restraints |
wR(F2) = 0.133 | All H-atom parameters refined |
S = 1.20 | Δρmax = 0.18 e Å−3 |
3067 reflections | Δρmin = −0.19 e Å−3 |
283 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
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)* |
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) |
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) |
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 |
Mr | 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) |
Tmin, Tmax | 0.971, 0.980 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15649, 3067, 2489 |
Rint | 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 |
Δρmax, Δρmin (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.
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. |
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).