Pyridin-4-ylmethane­diol: the hydrated form of isonicotinaldehyde

In the crystal structure of the title compound, C₆H₇NO₂, symmetry-related mol­ecules are linked by O—H...O hydrogen bonds to form centrosymmetric dimers. Adjacent dimers are linked by O—H...N hydrogen bonds to form a ribbon-like structure extending in the c direction. The ribbons are in turn linked by a C—H...O hydrogen bond to form a two-dimensional slab-like structure extending in the bc plane.

Key indicators

• Single-crystal X-ray study
• T = 153 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.036
• wR factor = 0.104
• Data-to-parameter ratio = 17.7

checkCIF/PLATON results

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Computing details

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Pyridin-4-ylmethanediol

Crystal data

C6H7NO2	Z = 2
Mr = 125.13	F(000) = 132
Triclinic, P1	Dx = 1.442 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.3197 (11) Å	Cell parameters from 3912 reflections
b = 6.9904 (11) Å	θ = 2.9–29.6°
c = 7.5711 (13) Å	µ = 0.11 mm^−1
α = 84.764 (13)°	T = 153 K
β = 69.546 (13)°	Block, colourless
γ = 67.036 (12)°	0.45 × 0.40 × 0.35 mm
V = 288.15 (8) Å^3

Data collection

Stoe IPDS-2 diffractometer	1368 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.030
Graphite monochromator	θmax = 29.5°, θmin = 2.9°
Detector resolution: 6.67 pixels mm^-1	h = −8→8
φ and ω scans	k = −9→9
3890 measured reflections	l = −9→10
1591 independent reflections

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0578P)^2 + 0.0448P] where P = (Fo^2 + 2Fc^2)/3
1591 reflections	(Δ/σ)max < 0.001
90 parameters	Δρmax = 0.29 e Å^−3
0 restraints	Δρmin = −0.22 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.79077 (14)	0.31377 (12)	0.98968 (10)	0.0254 (2)
O2	0.42507 (14)	0.26523 (13)	1.06179 (10)	0.0265 (2)
N1	0.76336 (16)	0.25574 (13)	0.35379 (11)	0.0224 (2)
C1	0.92560 (19)	0.27226 (16)	0.42073 (13)	0.0230 (3)
C2	0.90026 (18)	0.26052 (15)	0.61000 (13)	0.0213 (3)
C3	0.70027 (17)	0.22678 (14)	0.73776 (12)	0.0190 (2)
C4	0.53129 (18)	0.20958 (16)	0.66913 (14)	0.0229 (3)
C5	0.56957 (19)	0.22600 (16)	0.47756 (14)	0.0239 (3)
C6	0.67107 (18)	0.20191 (16)	0.94485 (13)	0.0219 (3)
H1	1.06470	0.29300	0.33430	0.0280*
H1O	0.781 (4)	0.284 (3)	1.118 (3)	0.074 (6)*
H2	1.01840	0.27540	0.65200	0.0260*
H2O	0.346 (3)	0.404 (3)	1.044 (2)	0.045 (4)*
H4	0.39160	0.18690	0.75210	0.0280*
H5	0.45200	0.21560	0.43200	0.0290*
H6	0.75620	0.05130	0.96300	0.0260*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0307 (4)	0.0367 (4)	0.0150 (3)	−0.0175 (3)	−0.0103 (3)	0.0032 (3)
O2	0.0282 (4)	0.0345 (4)	0.0160 (3)	−0.0162 (3)	−0.0024 (3)	0.0027 (3)
N1	0.0261 (4)	0.0251 (4)	0.0159 (4)	−0.0086 (3)	−0.0083 (3)	0.0008 (3)
C1	0.0246 (5)	0.0299 (5)	0.0151 (4)	−0.0127 (4)	−0.0050 (3)	0.0020 (3)
C2	0.0218 (4)	0.0281 (5)	0.0162 (4)	−0.0111 (4)	−0.0072 (3)	0.0012 (3)
C3	0.0215 (4)	0.0207 (4)	0.0146 (4)	−0.0076 (3)	−0.0064 (3)	0.0008 (3)
C4	0.0226 (5)	0.0299 (5)	0.0183 (4)	−0.0127 (4)	−0.0066 (3)	0.0020 (4)
C5	0.0255 (5)	0.0299 (5)	0.0195 (4)	−0.0114 (4)	−0.0105 (4)	0.0006 (4)
C6	0.0249 (5)	0.0276 (5)	0.0148 (4)	−0.0122 (4)	−0.0066 (3)	0.0032 (3)

Geometric parameters (Å, º)

O1—C6	1.4101 (15)	C3—C4	1.3872 (17)
O2—C6	1.4033 (15)	C3—C6	1.5151 (13)
O1—H1O	0.96 (2)	C4—C5	1.3862 (14)
O2—H2O	0.92 (2)	C1—H1	0.9500
N1—C5	1.3350 (16)	C2—H2	0.9500
N1—C1	1.3371 (17)	C4—H4	0.9500
C1—C2	1.3836 (14)	C5—H5	0.9500
C2—C3	1.3875 (15)	C6—H6	1.0000
O1···N1^i	2.7039 (12)	C4···H2O	2.901 (15)
O1···O2^ii	2.7755 (12)	C4···H5^ix	3.0900
O2···O1^ii	2.7755 (12)	C5···H1O^v	2.65 (2)
O2···C1^iii	3.3555 (15)	C6···H2O^ii	2.72 (2)
O1···H2O^ii	1.854 (19)	H1···O2^vii	2.4300
O1···H2	2.4400	H1···H2O^vii	2.5700
O2···H4	2.5500	H1O···N1^i	1.75 (2)
O2···H5^i	2.8500	H1O···C1^i	2.73 (2)
O2···H1^iii	2.4300	H1O···C5^i	2.65 (2)
O2···H6^iv	2.9100	H1O···H2O^ii	2.40 (3)
N1···O1^v	2.7039 (12)	H2···O1	2.4400
N1···C6^v	3.4225 (15)	H2···H4^x	2.5600
N1···C2^vi	3.4436 (14)	H2···H5^x	2.5500
N1···H1O^v	1.75 (2)	H2O···C4	2.901 (15)
C1···O2^vii	3.3555 (15)	H2O···H1^iii	2.5700
C1···C5^viii	3.5961 (17)	H2O···O1^ii	1.854 (19)
C1···C2^vi	3.4521 (15)	H2O···C3^ii	3.054 (19)
C1···C3^vi	3.3978 (15)	H2O···C6^ii	2.72 (2)
C2···N1^vi	3.4436 (14)	H2O···H1O^ii	2.40 (3)
C2···C1^vi	3.4521 (15)	H4···O2	2.5500
C3···C1^vi	3.3978 (15)	H4···H2^xi	2.5600
C5···C5^ix	3.5546 (17)	H5···O2^v	2.8500
C5···C1^viii	3.5961 (17)	H5···H2^xi	2.5500
C6···N1^i	3.4225 (15)	H5···C4^ix	3.0900
C1···H1O^v	2.73 (2)	H6···O2^iv	2.9100
C3···H2O^ii	3.054 (19)
C6—O1—H1O	105.1 (15)	O1—C6—C3	107.66 (9)
C6—O2—H2O	108.1 (12)	N1—C1—H1	118.00
C1—N1—C5	117.49 (9)	C2—C1—H1	118.00
N1—C1—C2	123.05 (11)	C1—C2—H2	120.00
C1—C2—C3	119.25 (11)	C3—C2—H2	120.00
C2—C3—C4	117.95 (9)	C3—C4—H4	121.00
C4—C3—C6	120.80 (10)	C5—C4—H4	121.00
C2—C3—C6	121.22 (10)	N1—C5—H5	118.00
C3—C4—C5	118.93 (11)	C4—C5—H5	118.00
N1—C5—C4	123.32 (12)	O1—C6—H6	108.00
O2—C6—C3	112.45 (10)	O2—C6—H6	108.00
O1—C6—O2	112.17 (8)	C3—C6—H6	108.00
C5—N1—C1—C2	−0.19 (15)	C6—C3—C4—C5	−177.72 (9)
C1—N1—C5—C4	−0.70 (15)	C2—C3—C6—O1	28.02 (13)
N1—C1—C2—C3	1.06 (15)	C2—C3—C6—O2	152.07 (9)
C1—C2—C3—C4	−1.03 (14)	C4—C3—C6—O1	−154.13 (9)
C1—C2—C3—C6	176.89 (9)	C4—C3—C6—O2	−30.07 (13)
C2—C3—C4—C5	0.21 (14)	C3—C4—C5—N1	0.69 (16)

Symmetry codes: (i) x, y, z+1; (ii) −x+1, −y+1, −z+2; (iii) x−1, y, z+1; (iv) −x+1, −y, −z+2; (v) x, y, z−1; (vi) −x+2, −y, −z+1; (vii) x+1, y, z−1; (viii) −x+1, −y+1, −z+1; (ix) −x+1, −y, −z+1; (x) x+1, y, z; (xi) x−1, y, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N1^i	0.96 (2)	1.75 (2)	2.7039 (12)	174 (2)
O2—H2O···O1^ii	0.92 (2)	1.85 (2)	2.7755 (12)	175 (2)
C1—H1···O2^vii	0.95	2.43	3.3555 (15)	163

Symmetry codes: (i) x, y, z+1; (ii) −x+1, −y+1, −z+2; (vii) x+1, y, z−1.