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In the title compound, C6H7N3O, there are inter- and intra­molecular N—H...N hydrogen bonds and an O—H...N hydrogen bond.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807046508/lw2034sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807046508/lw2034Isup2.hkl
Contains datablock I

CCDC reference: 664212

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.060
  • wR factor = 0.158
  • Data-to-parameter ratio = 14.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 1.02 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.69
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 0 ALERT type 5 Informative message, check

Comment top

Some derivatives of nicotinamidine is important chemical material. We report here the crystal structure of the title compound, (I).

The molecular structure of (I) is shown in Fig. 1,

Experimental top

Nicotinonitrile(20 mmol) was dissolved in ethanol (8 ml), hydroxylamine hydrochloride(20 mmol) was dissolved in ethanol (6 ml) and potassium carbonate (10 mmol) was dissolved in water (10 ml). The three separate solutions were mixed and the resulting mixture was refluxed for 24 h. After cooling and filtrating, the crude compound (I) was obtained. Pure compound (I) was obtained by crystallizing from a mixture of ethanol (6 ml) and water (2 ml). Crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of an ethanol solution. 1H NMR (CDCl3, δ, p.p.m.): 8.98 (s, 1H), 8.74 (m, 1H), 8.18 (m, 1H), 7.57 (m, 1H), 2.36 (s, 3H).

Refinement top

All H atoms bonded to the C atoms were placed geometrically at the distances of 0.93–0.97 Å and included in the refinement in riding motion approximation with Uiso(H) = 1.2 or 1.5Ueq of the carrier atom. The H atoms attached to N2 were located on a difference map and refined as isotropically asriding atoms. The H atom attached to O1 was refined as a riding atom at a distance of 0.82 Å from the O1 with Uĩso~(H) = 1.2U~eq~ of O1.

Structure description top

Some derivatives of nicotinamidine is important chemical material. We report here the crystal structure of the title compound, (I).

The molecular structure of (I) is shown in Fig. 1,

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo,1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXS97 (Sheldrick, 1997).

Figures top
[Figure 1] Fig. 1. A view of the molecular structure of (I), showing displacement ellipsoids at the 30% probability level. Dashed lines indicate N—H···N hydrogen bonds and O—H···N hydrogen bond
N'-Hydroxynicotinamidine top
Crystal data top
C6H7N3OF(000) = 288
Mr = 137.15Dx = 1.366 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -p 2ybcCell parameters from 25 reflections
a = 5.5220 (11) Åθ = 9–13°
b = 12.365 (3) ŵ = 0.10 mm1
c = 9.797 (2) ÅT = 293 K
β = 94.38 (3)°Block, colourless
V = 667.0 (3) Å30.20 × 0.20 × 0.10 mm
Z = 4
Data collection top
Enraf–Nonius CAD-4
diffractometer
782 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.053
Graphite monochromatorθmax = 26.0°, θmin = 2.7°
ω/2θ scansh = 66
Absorption correction: ψ scan
(North et al., 1968)
k = 015
Tmin = 0.951, Tmax = 0.970l = 012
1444 measured reflections3 standard reflections every 200 reflections
1307 independent reflections intensity decay: none
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)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.158H-atom parameters constrained
S = 1.16 w = 1/[σ2(Fo2) + (0.0466P)2 + 0.3602P]
where P = (Fo2 + 2Fc2)/3
1307 reflections(Δ/σ)max = 0.002
93 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.22 e Å3
Crystal data top
C6H7N3OV = 667.0 (3) Å3
Mr = 137.15Z = 4
Monoclinic, P21/cMo Kα radiation
a = 5.5220 (11) ŵ = 0.10 mm1
b = 12.365 (3) ÅT = 293 K
c = 9.797 (2) Å0.20 × 0.20 × 0.10 mm
β = 94.38 (3)°
Data collection top
Enraf–Nonius CAD-4
diffractometer
782 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.053
Tmin = 0.951, Tmax = 0.9703 standard reflections every 200 reflections
1444 measured reflections intensity decay: none
1307 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0600 restraints
wR(F2) = 0.158H-atom parameters constrained
S = 1.16Δρmax = 0.21 e Å3
1307 reflectionsΔρmin = 0.22 e Å3
93 parameters
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
O10.6266 (4)0.85703 (19)0.2247 (2)0.0575 (7)
H1A0.68000.86300.14920.086*
N10.1856 (5)0.6347 (2)0.4713 (3)0.0523 (7)
N20.4172 (5)0.8367 (2)0.4451 (3)0.0538 (8)
H2A0.56970.87760.43550.072 (11)*
H2B0.46640.81360.53870.111 (16)*
N30.4391 (5)0.7778 (2)0.2184 (3)0.0466 (7)
C10.2182 (6)0.5548 (3)0.3844 (4)0.0564 (9)
H1B0.34600.50730.39530.068*
C20.0749 (6)0.5366 (3)0.2776 (4)0.0568 (9)
H2C0.10670.47940.21720.068*
C30.1172 (6)0.6057 (3)0.2633 (3)0.0501 (9)
H3B0.22060.59420.19410.060*
C40.1560 (6)0.6916 (2)0.3512 (3)0.0424 (8)
C50.0006 (6)0.7027 (3)0.4547 (3)0.0468 (8)
H5A0.02590.75990.51580.056*
C60.3564 (5)0.7710 (2)0.3388 (3)0.0406 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0685 (16)0.0605 (15)0.0481 (13)0.0083 (13)0.0346 (11)0.0048 (12)
N10.0523 (17)0.0572 (17)0.0510 (16)0.0048 (15)0.0278 (13)0.0007 (15)
N20.071 (2)0.0523 (17)0.0416 (16)0.0005 (15)0.0278 (14)0.0007 (14)
N30.0516 (16)0.0485 (16)0.0433 (15)0.0003 (13)0.0275 (12)0.0037 (12)
C10.055 (2)0.058 (2)0.059 (2)0.0029 (18)0.0205 (18)0.0033 (18)
C20.073 (2)0.0444 (19)0.056 (2)0.0005 (19)0.0236 (18)0.0053 (17)
C30.062 (2)0.052 (2)0.0397 (17)0.0036 (18)0.0284 (16)0.0020 (15)
C40.0523 (19)0.0395 (17)0.0384 (16)0.0085 (15)0.0235 (14)0.0056 (13)
C50.0506 (18)0.0514 (19)0.0417 (17)0.0002 (17)0.0247 (15)0.0041 (15)
C60.0460 (18)0.0427 (18)0.0355 (16)0.0118 (14)0.0194 (13)0.0068 (14)
Geometric parameters (Å, º) top
O1—N31.423 (3)C1—H1B0.9300
O1—H1A0.8200C2—C31.378 (4)
N1—C11.308 (4)C2—H2C0.9300
N1—C51.348 (4)C3—C41.373 (4)
N2—C61.343 (4)C3—H3B0.9300
N2—H2A0.9929C4—C51.385 (4)
N2—H2B0.9787C4—C61.491 (4)
N3—C61.300 (4)C5—H5A0.9300
C1—C21.378 (4)
N3—O1—H1A109.5C4—C3—C2120.0 (3)
C1—N1—C5117.5 (3)C4—C3—H3B120.0
C6—N2—H2A113.5C2—C3—H3B120.0
C6—N2—H2B125.8C3—C4—C5117.4 (3)
H2A—N2—H2B93.5C3—C4—C6122.6 (3)
C6—N3—O1108.1 (2)C5—C4—C6119.9 (3)
N1—C1—C2124.0 (3)N1—C5—C4123.2 (3)
N1—C1—H1B118.0N1—C5—H5A118.4
C2—C1—H1B118.0C4—C5—H5A118.4
C3—C2—C1117.9 (3)N3—C6—N2125.5 (3)
C3—C2—H2C121.1N3—C6—C4115.5 (3)
C1—C2—H2C121.1N2—C6—C4118.6 (2)
C5—N1—C1—C20.2 (5)C6—C4—C5—N1179.3 (3)
N1—C1—C2—C31.3 (5)O1—N3—C6—N27.4 (4)
C1—C2—C3—C42.1 (5)O1—N3—C6—C4179.7 (2)
C2—C3—C4—C51.9 (5)C3—C4—C6—N322.5 (4)
C2—C3—C4—C6178.3 (3)C5—C4—C6—N3157.7 (3)
C1—N1—C5—C40.0 (5)C3—C4—C6—N2164.7 (3)
C3—C4—C5—N10.9 (5)C5—C4—C6—N215.1 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2B···N3i0.982.113.023 (4)155
O1—H1A···N1ii0.821.952.767 (4)176
N2—H2A···O10.992.132.539 (4)103
Symmetry codes: (i) x, y+3/2, z+1/2; (ii) x+1, y+3/2, z1/2.

Experimental details

Crystal data
Chemical formulaC6H7N3O
Mr137.15
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)5.5220 (11), 12.365 (3), 9.797 (2)
β (°) 94.38 (3)
V3)667.0 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.20 × 0.20 × 0.10
Data collection
DiffractometerEnraf–Nonius CAD-4
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.951, 0.970
No. of measured, independent and
observed [I > 2σ(I)] reflections
1444, 1307, 782
Rint0.053
(sin θ/λ)max1)0.616
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.060, 0.158, 1.16
No. of reflections1307
No. of parameters93
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.21, 0.22

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo,1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Siemens, 1996).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2B···N3i0.982.113.023 (4)155
O1—H1A···N1ii0.821.952.767 (4)176
N2—H2A···O10.992.132.539 (4)103
Symmetry codes: (i) x, y+3/2, z+1/2; (ii) x+1, y+3/2, z1/2.
 

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