Di-4-pyridylmethane-diol.

In the title compound, C(11)H(10)N(2)O(2), individual mol-ecules lie across crystallographic twofold rotation axes. Neighboring mol-ecules engage in O-H⋯N hydrogen bonding, forming square-grid layers parallel to the ab plane.

Related literature

For related literature, see: Chen & Mak (2005 ▶); Montney et al. (2008 ▶); Zaworotko (2007 ▶).

Experimental

Crystal data

C11H10N2O2

M = 202.21

Tetragonal,

a = 7.6130 (2) Å

c = 17.5864 (11) Å

V = 1019.27 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 173 (2) K

0.30 × 0.22 × 0.16 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.686, T max = 0.745 (expected range = 0.907–0.985)

14287 measured reflections

605 independent reflections

549 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.076

S = 1.13

605 reflections

72 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.13 e Å−3

Δρmin = −0.13 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶) and COSMO (Bruker, 2006 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2006 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Crystal Maker (Palmer, 2007 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808018588/hg2417sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808018588/hg2417Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C11H10N2O2	Z = 4
Mr = 202.21	F000 = 424
Tetragonal, P43212	Dx = 1.318 Mg m−3
Hall symbol: P 4nw 2abw	Mo Kα radiation λ = 0.71073 Å
a = 7.6130 (2) Å	Cell parameters from 14287 reflections
b = 7.6130 (2) Å	θ = 2.9–25.3º
c = 17.5864 (11) Å	µ = 0.09 mm−1
α = 90º	T = 173 (2) K
β = 90º	Block, colourless
γ = 90º	0.30 × 0.22 × 0.16 mm
V = 1019.27 (7) Å3

Bruker APEXII diffractometer	605 independent reflections
Radiation source: fine-focus sealed tube	549 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.040
T = 173(2) K	θmax = 25.3º
ω and ψ scans	θmin = 2.9º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −8→9
Tmin = 0.686, Tmax = 0.745	k = −9→9
14287 measured reflections	l = −21→20

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.029	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.076	w = 1/[σ2(Fo2) + (0.0412P)2 + 0.1593P] where P = (Fo2 + 2Fc2)/3
S = 1.13	(Δ/σ)max < 0.001
605 reflections	Δρmax = 0.13 e Å−3
72 parameters	Δρmin = −0.12 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq
O1	0.62268 (16)	0.65611 (15)	0.06536 (7)	0.0256 (3)
H1A	0.616 (3)	0.768 (3)	0.0580 (11)	0.031*
N1	0.6238 (2)	0.01378 (19)	0.04930 (8)	0.0317 (4)
C1	0.5269 (3)	0.1201 (3)	0.09305 (11)	0.0377 (5)
H1	0.4681	0.0717	0.1344	0.045*
C2	0.5099 (3)	0.2974 (2)	0.07980 (10)	0.0322 (5)
H2	0.4422	0.3665	0.1121	0.039*
C3	0.5945 (2)	0.3724 (2)	0.01785 (9)	0.0216 (4)
C4	0.6967 (2)	0.2639 (2)	−0.02701 (10)	0.0263 (4)
H4	0.7573	0.3089	−0.0686	0.032*
C5	0.7075 (2)	0.0872 (2)	−0.00905 (11)	0.0307 (5)
H5	0.7772	0.0157	−0.0395	0.037*
C6	0.5671 (2)	0.5671 (2)	0.0000	0.0207 (5)

	U11	U22	U33	U12	U13	U23
O1	0.0303 (7)	0.0177 (6)	0.0287 (7)	−0.0006 (5)	−0.0056 (6)	−0.0012 (5)
N1	0.0390 (10)	0.0217 (8)	0.0343 (8)	0.0022 (7)	−0.0040 (8)	0.0004 (7)
C1	0.0455 (13)	0.0300 (11)	0.0377 (10)	0.0023 (10)	0.0098 (9)	0.0074 (9)
C2	0.0352 (11)	0.0266 (10)	0.0349 (10)	0.0056 (8)	0.0095 (9)	0.0023 (8)
C3	0.0196 (9)	0.0221 (9)	0.0232 (8)	−0.0007 (7)	−0.0047 (7)	−0.0016 (7)
C4	0.0267 (10)	0.0256 (10)	0.0264 (9)	0.0007 (8)	0.0018 (8)	−0.0017 (8)
C5	0.0342 (10)	0.0254 (10)	0.0325 (10)	0.0059 (8)	−0.0021 (9)	−0.0057 (9)
C6	0.0208 (8)	0.0208 (8)	0.0205 (11)	0.0008 (10)	0.0002 (7)	−0.0002 (7)

O1—C6	1.3998 (17)	C3—C4	1.382 (2)
O1—H1A	0.87 (2)	C3—C6	1.529 (2)
N1—C5	1.331 (2)	C4—C5	1.384 (2)
N1—C1	1.338 (2)	C4—H4	0.9300
C1—C2	1.376 (3)	C5—H5	0.9300
C1—H1	0.9300	C6—O1i	1.3998 (17)
C2—C3	1.389 (2)	C6—C3i	1.529 (2)
C2—H2	0.9300
C6—O1—H1A	109.7 (13)	C3—C4—H4	120.5
C5—N1—C1	116.94 (15)	C5—C4—H4	120.5
N1—C1—C2	123.20 (17)	N1—C5—C4	123.77 (17)
N1—C1—H1	118.4	N1—C5—H5	118.1
C2—C1—H1	118.4	C4—C5—H5	118.1
C1—C2—C3	119.53 (17)	O1—C6—O1i	112.43 (19)
C1—C2—H2	120.2	O1—C6—C3	105.03 (8)
C3—C2—H2	120.2	O1i—C6—C3	113.29 (8)
C4—C3—C2	117.59 (16)	O1—C6—C3i	113.30 (8)
C4—C3—C6	122.61 (14)	O1i—C6—C3i	105.03 (8)
C2—C3—C6	119.76 (14)	C3—C6—C3i	107.87 (19)
C3—C4—C5	118.94 (17)
C5—N1—C1—C2	0.6 (3)	C3—C4—C5—N1	0.3 (3)
N1—C1—C2—C3	0.8 (3)	C4—C3—C6—O1	−123.43 (16)
C1—C2—C3—C4	−1.6 (3)	C2—C3—C6—O1	58.9 (2)
C1—C2—C3—C6	176.25 (17)	C4—C3—C6—O1i	−0.4 (2)
C2—C3—C4—C5	1.0 (3)	C2—C3—C6—O1i	−178.06 (15)
C6—C3—C4—C5	−176.72 (15)	C4—C3—C6—C3i	115.45 (17)
C1—N1—C5—C4	−1.1 (3)	C2—C3—C6—C3i	−62.25 (14)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1ii	0.87 (2)	1.87 (2)	2.7376 (19)	173.4 (19)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N1i	0.87 (2)	1.87 (2)	2.7376 (19)	173.4 (19)

Symmetry code: (i) .