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The molecule of the title compound, C6H8N2O, is almost planar; the hydroxy­methyl group deviates slightly from the plane of the ring. The mol­ecules are linked into a chain running along the a-axis direction by an O—H...N hydrogen bond. N—H...O and N—H...N hydrogen bonds connect the chains, forming a mol­ecular layer parallel to the (001) plane. A C—H...π inter­action is also observed in the layer.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806025499/is2056sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806025499/is2056Isup2.hkl
Contains datablock I

CCDC reference: 295733

Key indicators

  • Single-crystal X-ray study
  • T = 297 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.042
  • wR factor = 0.117
  • Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 3
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

2-Amino-6-(hydroxymethyl)pyridine top
Crystal data top
C6H8N2OF(000) = 264
Mr = 124.14Dx = 1.295 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1373 reflections
a = 6.9279 (2) Åθ = 2.1–29.0°
b = 4.7570 (1) ŵ = 0.09 mm1
c = 19.3436 (5) ÅT = 297 K
β = 92.657 (2)°Block, colourless
V = 636.80 (3) Å30.44 × 0.36 × 0.23 mm
Z = 4
Data collection top
Bruker SMART APEX2 CCD area-detector
diffractometer
1699 independent reflections
Radiation source: fine-focus sealed tube1373 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
Detector resolution: 8.33 pixels mm-1θmax = 29.0°, θmin = 2.1°
ω scansh = 99
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 66
Tmin = 0.961, Tmax = 0.979l = 2626
8090 measured 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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117All H-atom parameters refined
S = 1.04 w = 1/[σ2(Fo2) + (0.0591P)2 + 0.0978P]
where P = (Fo2 + 2Fc2)/3
1699 reflections(Δ/σ)max < 0.001
114 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = 0.22 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.13559 (13)0.2220 (2)0.11410 (6)0.0556 (3)
N10.34165 (12)0.4952 (2)0.08010 (5)0.0361 (2)
N20.64074 (15)0.7070 (3)0.07044 (6)0.0485 (3)
C10.47416 (15)0.6739 (2)0.10652 (6)0.0363 (3)
C20.45329 (18)0.8128 (3)0.16953 (6)0.0439 (3)
C30.29098 (18)0.7615 (3)0.20516 (6)0.0475 (3)
C40.15234 (17)0.5746 (3)0.17874 (6)0.0440 (3)
C50.18320 (14)0.4471 (2)0.11606 (5)0.0353 (3)
C60.04437 (17)0.2388 (3)0.08254 (7)0.0430 (3)
H20.553 (2)0.946 (3)0.1864 (8)0.060 (4)*
H30.275 (2)0.855 (3)0.2490 (8)0.055 (4)*
H40.041 (2)0.533 (3)0.2039 (8)0.058 (4)*
H6A0.103 (2)0.053 (4)0.0854 (8)0.054 (4)*
H6B0.028 (2)0.292 (3)0.0330 (9)0.060 (4)*
H1N20.629 (2)0.668 (3)0.0258 (9)0.058 (4)*
H2N20.711 (2)0.859 (4)0.0807 (9)0.065 (5)*
H1O10.198 (3)0.377 (5)0.1003 (10)0.083 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0353 (5)0.0545 (6)0.0782 (7)0.0131 (4)0.0130 (4)0.0059 (5)
N10.0306 (4)0.0370 (5)0.0410 (5)0.0046 (4)0.0061 (3)0.0018 (4)
N20.0355 (5)0.0572 (7)0.0537 (6)0.0159 (5)0.0116 (4)0.0126 (5)
C10.0294 (5)0.0376 (6)0.0420 (5)0.0019 (4)0.0032 (4)0.0010 (4)
C20.0393 (6)0.0478 (7)0.0444 (6)0.0038 (5)0.0001 (4)0.0071 (5)
C30.0485 (7)0.0559 (8)0.0384 (6)0.0031 (6)0.0050 (5)0.0058 (5)
C40.0381 (6)0.0519 (7)0.0432 (6)0.0004 (5)0.0126 (4)0.0040 (5)
C50.0298 (5)0.0340 (5)0.0423 (5)0.0003 (4)0.0048 (4)0.0069 (4)
C60.0327 (5)0.0404 (7)0.0561 (7)0.0068 (5)0.0055 (5)0.0036 (5)
Geometric parameters (Å, º) top
O1—C61.4156 (14)C2—H20.984 (17)
O1—H1O10.89 (2)C3—C41.3888 (18)
N1—C11.3353 (14)C3—H30.968 (16)
N1—C51.3460 (13)C4—C51.3813 (16)
N2—C11.3850 (14)C4—H40.954 (15)
N2—H1N20.883 (17)C5—C61.5065 (16)
N2—H2N20.889 (19)C6—H6A0.971 (16)
C1—C21.3997 (16)C6—H6B0.992 (17)
C2—C31.3676 (17)
C6—O1—H1O1104.6 (12)C4—C3—H3120.6 (9)
C1—N1—C5118.24 (9)C5—C4—C3118.14 (10)
C1—N2—H1N2115.3 (10)C5—C4—H4121.2 (9)
C1—N2—H2N2116.0 (10)C3—C4—H4120.6 (9)
H1N2—N2—H2N2114.6 (15)N1—C5—C4122.82 (10)
N1—C1—N2116.98 (10)N1—C5—C6114.15 (10)
N1—C1—C2122.46 (10)C4—C5—C6123.02 (10)
N2—C1—C2120.48 (10)O1—C6—C5114.14 (10)
C3—C2—C1118.38 (11)O1—C6—H6A107.2 (9)
C3—C2—H2122.1 (9)C5—C6—H6A108.5 (9)
C1—C2—H2119.5 (9)O1—C6—H6B111.7 (10)
C2—C3—C4119.96 (11)C5—C6—H6B106.8 (9)
C2—C3—H3119.4 (9)H6A—C6—H6B108.3 (13)
C5—N1—C1—N2176.38 (10)C1—N1—C5—C40.07 (16)
C5—N1—C1—C20.40 (17)C1—N1—C5—C6178.99 (10)
N1—C1—C2—C30.22 (18)C3—C4—C5—N10.42 (18)
N2—C1—C2—C3176.45 (11)C3—C4—C5—C6179.40 (11)
C1—C2—C3—C40.29 (19)N1—C5—C6—O1170.27 (10)
C2—C3—C4—C50.59 (19)C4—C5—C6—O110.67 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O1···N2i0.89 (2)2.00 (2)2.8837 (16)175 (2)
N2—H2N2···O1ii0.889 (18)2.113 (18)2.9991 (16)174.5 (15)
N2—H1N2···N1iii0.883 (17)2.209 (17)3.0745 (15)166.5 (13)
C6—H6A···Cg1iv0.971 (16)2.711 (17)3.6257 (14)156.8 (12)
Symmetry codes: (i) x1, y, z; (ii) x+1, y+1, z; (iii) x+1, y+1, z; (iv) x, y1, z.
 

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