2,3-Di-4-pyridylbutane-2,3-diol

The mol­ecule of the title compound, C₁₄H₁₆N₂O₂, lies on a centre of inversion located at the mid-point of the central C—C bond. O–H...N hydrogen bonds link adjacent mol­ecules into a layer motif.

Key indicators

• Single-crystal X-ray study
• T = 291 K
• Mean [sigma](C-C)= 0.002 Å
• R factor = 0.037
• wR factor = 0.103
• Data-to-parameter ratio = 12.1

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

2,3-Di-4-pyridylbutane-2,3-diol

Crystal data

C14H16N2O2	F(000) = 520
Mr = 244.29	Dx = 1.358 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1618 reflections
a = 12.408 (1) Å	θ = 2.7–26.3°
b = 6.4174 (6) Å	µ = 0.09 mm^−1
c = 15.004 (2) Å	T = 291 K
V = 1194.8 (2) Å^3	Block, colourless
Z = 4	0.26 × 0.14 × 0.06 mm

Data collection

Bruker APEX-II area-detector diffractometer	1049 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.030
Graphite monochromator	θmax = 27.5°, θmin = 2.7°
φ and ω scans	h = −11→16
6611 measured reflections	k = −8→7
1376 independent reflections	l = −18→19

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.037	Hydrogen site location: difference Fourier map
wR(F^2) = 0.103	All H-atom parameters refined
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0495P)^2 + 0.2502P] where P = (Fo^2 + 2Fc^2)/3
1376 reflections	(Δ/σ)max = 0.001
114 parameters	Δρmax = 0.21 e Å^−3
8 restraints	Δρmin = −0.15 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.5512 (1)	0.7362 (2)	0.4463 (1)	0.0417 (3)
N1	0.6308 (1)	0.7454 (2)	0.7698 (1)	0.0416 (3)
C1	0.6429 (1)	0.4041 (3)	0.4616 (1)	0.0416 (4)
C2	0.5581 (1)	0.5525 (2)	0.4989 (1)	0.0332 (3)
C3	0.5878 (1)	0.6206 (2)	0.5936 (1)	0.0333 (3)
C4	0.6310 (1)	0.4833 (2)	0.6559 (1)	0.0388 (4)
C5	0.6501 (1)	0.5523 (2)	0.7420 (1)	0.0414 (4)
C6	0.5928 (1)	0.8777 (2)	0.7088 (1)	0.0413 (4)
C7	0.5707 (1)	0.8238 (2)	0.6216 (1)	0.0385 (4)
H1	0.584 (1)	0.718 (3)	0.396 (1)	0.067 (6)*
H11	0.631 (1)	0.380 (3)	0.399 (1)	0.059 (5)*
H12	0.639 (1)	0.270 (2)	0.490 (1)	0.046 (4)*
H13	0.714 (1)	0.461 (2)	0.469 (1)	0.062 (5)*
H4	0.645 (1)	0.340 (2)	0.642 (1)	0.045 (4)*
H5	0.678 (1)	0.456 (2)	0.786 (1)	0.045 (4)*
H6	0.582 (1)	1.019 (2)	0.729 (1)	0.048 (4)*
H7	0.543 (1)	0.926 (2)	0.582 (1)	0.045 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0607 (7)	0.0386 (6)	0.0258 (5)	0.0032 (5)	0.0049 (5)	0.0054 (4)
N1	0.0439 (7)	0.0529 (8)	0.0279 (6)	−0.0038 (6)	0.0005 (5)	−0.0044 (5)
C1	0.0450 (9)	0.0462 (9)	0.0335 (8)	0.0047 (7)	0.0055 (6)	−0.0048 (7)
C2	0.0440 (8)	0.0332 (7)	0.0225 (6)	0.0048 (6)	0.0012 (5)	0.0016 (5)
C3	0.0366 (7)	0.0382 (8)	0.0251 (6)	0.0014 (6)	0.0027 (5)	−0.0001 (5)
C4	0.0457 (8)	0.0408 (8)	0.0298 (7)	0.0065 (6)	−0.0016 (6)	0.0006 (6)
C5	0.0428 (8)	0.053 (1)	0.0283 (7)	0.0025 (7)	−0.0032 (6)	0.0045 (6)
C6	0.0460 (9)	0.0428 (9)	0.0351 (7)	−0.0019 (7)	0.0016 (6)	−0.0074 (6)
C7	0.0465 (8)	0.0376 (8)	0.0312 (7)	0.0024 (6)	−0.0002 (6)	−0.0002 (6)

Geometric parameters (Å, º)

O1—C2	1.421 (2)	C6—C7	1.381 (2)
N1—C5	1.329 (2)	O1—H1	0.86 (1)
N1—C6	1.335 (2)	C1—H11	0.96 (1)
C1—C2	1.526 (2)	C1—H12	0.96 (1)
C2—C3	1.532 (2)	C1—H13	0.96 (1)
C2—C2^i	1.591 (3)	C4—H4	0.96 (1)
C3—C7	1.386 (2)	C5—H5	0.96 (1)
C3—C4	1.392 (2)	C6—H6	0.97 (1)
C4—C5	1.386 (2)	C7—H7	0.95 (1)
C5—N1—C6	116.2 (1)	C2—C1—H11	111 (1)
O1—C2—C1	110.8 (1)	C2—C1—H12	111 (1)
O1—C2—C3	107.1 (1)	H11—C1—H12	106 (2)
C1—C2—C3	110.6 (1)	C2—C1—H13	111 (1)
O1—C2—C2^i	108.0 (1)	H11—C1—H13	108 (2)
C1—C2—C2^i	111.6 (1)	H12—C1—H13	110 (1)
C3—C2—C2^i	108.6 (1)	C5—C4—H4	119 (1)
C7—C3—C4	116.8 (1)	C3—C4—H4	122 (1)
C7—C3—C2	120.8 (1)	N1—C5—H5	117 (1)
C4—C3—C2	122.4 (1)	C4—C5—H5	119 (1)
C5—C4—C3	119.3 (1)	N1—C6—H6	116 (1)
N1—C5—C4	124.0 (1)	C7—C6—H6	120 (1)
N1—C6—C7	124.1 (1)	C6—C7—H7	119 (1)
C6—C7—C3	119.5 (1)	C3—C7—H7	121 (1)
C2—O1—H1	110 (1)
O1—C2—C3—C7	20.1 (2)	C2—C3—C4—C5	−176.2 (2)
C1—C2—C3—C7	140.9 (1)	C6—N1—C5—C4	−1.4 (2)
C2^i—C2—C3—C7	−96.4 (2)	C3—C4—C5—N1	−0.8 (2)
O1—C2—C3—C4	−161.1 (1)	C5—N1—C6—C7	1.7 (2)
C1—C2—C3—C4	−40.3 (2)	N1—C6—C7—C3	0.2 (2)
C2^i—C2—C3—C4	82.5 (2)	C4—C3—C7—C6	−2.4 (2)
C7—C3—C4—C5	2.7 (2)	C2—C3—C7—C6	176.5 (1)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1^ii	0.86 (1)	2.00 (1)	2.829 (2)	161 (2)

Symmetry code: (ii) x, −y+3/2, z−1/2.