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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806043303/bv2038sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806043303/bv2038Isup2.hkl
Contains datablock I

CCDC reference: 627364

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

No syntax errors found



Alert level C PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

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 top
Crystal data top
C6H7NO2Z = 2
Mr = 125.13F(000) = 132
Triclinic, P1Dx = 1.442 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.3197 (11) ÅCell parameters from 3912 reflections
b = 6.9904 (11) Åθ = 2.9–29.6°
c = 7.5711 (13) ŵ = 0.11 mm1
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) Å3
Data collection top
Stoe IPDS-2
diffractometer
1368 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.030
Graphite monochromatorθmax = 29.5°, θmin = 2.9°
Detector resolution: 6.67 pixels mm-1h = 88
φ and ω scansk = 99
3890 measured reflectionsl = 910
1591 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104H atoms treated by a mixture of independent and constrained refinement
S = 1.08 w = 1/[σ2(Fo2) + (0.0578P)2 + 0.0448P]
where P = (Fo2 + 2Fc2)/3
1591 reflections(Δ/σ)max < 0.001
90 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = 0.22 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
O10.79077 (14)0.31377 (12)0.98968 (10)0.0254 (2)
O20.42507 (14)0.26523 (13)1.06179 (10)0.0265 (2)
N10.76336 (16)0.25574 (13)0.35379 (11)0.0224 (2)
C10.92560 (19)0.27226 (16)0.42073 (13)0.0230 (3)
C20.90026 (18)0.26052 (15)0.61000 (13)0.0213 (3)
C30.70027 (17)0.22678 (14)0.73776 (12)0.0190 (2)
C40.53129 (18)0.20958 (16)0.66913 (14)0.0229 (3)
C50.56957 (19)0.22600 (16)0.47756 (14)0.0239 (3)
C60.67107 (18)0.20191 (16)0.94485 (13)0.0219 (3)
H11.064700.293000.334300.0280*
H1O0.781 (4)0.284 (3)1.118 (3)0.074 (6)*
H21.018400.275400.652000.0260*
H2O0.346 (3)0.404 (3)1.044 (2)0.045 (4)*
H40.391600.186900.752100.0280*
H50.452000.215600.432000.0290*
H60.756200.051300.963000.0260*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0307 (4)0.0367 (4)0.0150 (3)0.0175 (3)0.0103 (3)0.0032 (3)
O20.0282 (4)0.0345 (4)0.0160 (3)0.0162 (3)0.0024 (3)0.0027 (3)
N10.0261 (4)0.0251 (4)0.0159 (4)0.0086 (3)0.0083 (3)0.0008 (3)
C10.0246 (5)0.0299 (5)0.0151 (4)0.0127 (4)0.0050 (3)0.0020 (3)
C20.0218 (4)0.0281 (5)0.0162 (4)0.0111 (4)0.0072 (3)0.0012 (3)
C30.0215 (4)0.0207 (4)0.0146 (4)0.0076 (3)0.0064 (3)0.0008 (3)
C40.0226 (5)0.0299 (5)0.0183 (4)0.0127 (4)0.0066 (3)0.0020 (4)
C50.0255 (5)0.0299 (5)0.0195 (4)0.0114 (4)0.0105 (4)0.0006 (4)
C60.0249 (5)0.0276 (5)0.0148 (4)0.0122 (4)0.0066 (3)0.0032 (3)
Geometric parameters (Å, º) top
O1—C61.4101 (15)C3—C41.3872 (17)
O2—C61.4033 (15)C3—C61.5151 (13)
O1—H1O0.96 (2)C4—C51.3862 (14)
O2—H2O0.92 (2)C1—H10.9500
N1—C51.3350 (16)C2—H20.9500
N1—C11.3371 (17)C4—H40.9500
C1—C21.3836 (14)C5—H50.9500
C2—C31.3875 (15)C6—H61.0000
O1···N1i2.7039 (12)C4···H2O2.901 (15)
O1···O2ii2.7755 (12)C4···H5ix3.0900
O2···O1ii2.7755 (12)C5···H1Ov2.65 (2)
O2···C1iii3.3555 (15)C6···H2Oii2.72 (2)
O1···H2Oii1.854 (19)H1···O2vii2.4300
O1···H22.4400H1···H2Ovii2.5700
O2···H42.5500H1O···N1i1.75 (2)
O2···H5i2.8500H1O···C1i2.73 (2)
O2···H1iii2.4300H1O···C5i2.65 (2)
O2···H6iv2.9100H1O···H2Oii2.40 (3)
N1···O1v2.7039 (12)H2···O12.4400
N1···C6v3.4225 (15)H2···H4x2.5600
N1···C2vi3.4436 (14)H2···H5x2.5500
N1···H1Ov1.75 (2)H2O···C42.901 (15)
C1···O2vii3.3555 (15)H2O···H1iii2.5700
C1···C5viii3.5961 (17)H2O···O1ii1.854 (19)
C1···C2vi3.4521 (15)H2O···C3ii3.054 (19)
C1···C3vi3.3978 (15)H2O···C6ii2.72 (2)
C2···N1vi3.4436 (14)H2O···H1Oii2.40 (3)
C2···C1vi3.4521 (15)H4···O22.5500
C3···C1vi3.3978 (15)H4···H2xi2.5600
C5···C5ix3.5546 (17)H5···O2v2.8500
C5···C1viii3.5961 (17)H5···H2xi2.5500
C6···N1i3.4225 (15)H5···C4ix3.0900
C1···H1Ov2.73 (2)H6···O2iv2.9100
C3···H2Oii3.054 (19)
C6—O1—H1O105.1 (15)O1—C6—C3107.66 (9)
C6—O2—H2O108.1 (12)N1—C1—H1118.00
C1—N1—C5117.49 (9)C2—C1—H1118.00
N1—C1—C2123.05 (11)C1—C2—H2120.00
C1—C2—C3119.25 (11)C3—C2—H2120.00
C2—C3—C4117.95 (9)C3—C4—H4121.00
C4—C3—C6120.80 (10)C5—C4—H4121.00
C2—C3—C6121.22 (10)N1—C5—H5118.00
C3—C4—C5118.93 (11)C4—C5—H5118.00
N1—C5—C4123.32 (12)O1—C6—H6108.00
O2—C6—C3112.45 (10)O2—C6—H6108.00
O1—C6—O2112.17 (8)C3—C6—H6108.00
C5—N1—C1—C20.19 (15)C6—C3—C4—C5177.72 (9)
C1—N1—C5—C40.70 (15)C2—C3—C6—O128.02 (13)
N1—C1—C2—C31.06 (15)C2—C3—C6—O2152.07 (9)
C1—C2—C3—C41.03 (14)C4—C3—C6—O1154.13 (9)
C1—C2—C3—C6176.89 (9)C4—C3—C6—O230.07 (13)
C2—C3—C4—C50.21 (14)C3—C4—C5—N10.69 (16)
Symmetry codes: (i) x, y, z+1; (ii) x+1, y+1, z+2; (iii) x1, y, z+1; (iv) x+1, y, z+2; (v) x, y, z1; (vi) x+2, y, z+1; (vii) x+1, y, z1; (viii) x+1, y+1, z+1; (ix) x+1, y, z+1; (x) x+1, y, z; (xi) x1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O···N1i0.96 (2)1.75 (2)2.7039 (12)174 (2)
O2—H2O···O1ii0.92 (2)1.85 (2)2.7755 (12)175 (2)
C1—H1···O2vii0.952.433.3555 (15)163
Symmetry codes: (i) x, y, z+1; (ii) x+1, y+1, z+2; (vii) x+1, y, z1.
 

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