Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807046508/lw2034sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807046508/lw2034Isup2.hkl |
CCDC reference: 664212
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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).
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.
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,
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).
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 |
C6H7N3O | F(000) = 288 |
Mr = 137.15 | Dx = 1.366 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -p 2ybc | Cell parameters from 25 reflections |
a = 5.5220 (11) Å | θ = 9–13° |
b = 12.365 (3) Å | µ = 0.10 mm−1 |
c = 9.797 (2) Å | T = 293 K |
β = 94.38 (3)° | Block, colourless |
V = 667.0 (3) Å3 | 0.20 × 0.20 × 0.10 mm |
Z = 4 |
Enraf–Nonius CAD-4 diffractometer | 782 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.053 |
Graphite monochromator | θmax = 26.0°, θmin = 2.7° |
ω/2θ scans | h = −6→6 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→15 |
Tmin = 0.951, Tmax = 0.970 | l = 0→12 |
1444 measured reflections | 3 standard reflections every 200 reflections |
1307 independent reflections | intensity decay: none |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.060 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.158 | H-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 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
C6H7N3O | V = 667.0 (3) Å3 |
Mr = 137.15 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 5.5220 (11) Å | µ = 0.10 mm−1 |
b = 12.365 (3) Å | T = 293 K |
c = 9.797 (2) Å | 0.20 × 0.20 × 0.10 mm |
β = 94.38 (3)° |
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 = 0.970 | 3 standard reflections every 200 reflections |
1444 measured reflections | intensity decay: none |
1307 independent reflections |
R[F2 > 2σ(F2)] = 0.060 | 0 restraints |
wR(F2) = 0.158 | H-atom parameters constrained |
S = 1.16 | Δρmax = 0.21 e Å−3 |
1307 reflections | Δρmin = −0.22 e Å−3 |
93 parameters |
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 | 0.6266 (4) | 0.85703 (19) | 0.2247 (2) | 0.0575 (7) | |
H1A | 0.6800 | 0.8630 | 0.1492 | 0.086* | |
N1 | −0.1856 (5) | 0.6347 (2) | 0.4713 (3) | 0.0523 (7) | |
N2 | 0.4172 (5) | 0.8367 (2) | 0.4451 (3) | 0.0538 (8) | |
H2A | 0.5697 | 0.8776 | 0.4355 | 0.072 (11)* | |
H2B | 0.4664 | 0.8136 | 0.5387 | 0.111 (16)* | |
N3 | 0.4391 (5) | 0.7778 (2) | 0.2184 (3) | 0.0466 (7) | |
C1 | −0.2182 (6) | 0.5548 (3) | 0.3844 (4) | 0.0564 (9) | |
H1B | −0.3460 | 0.5073 | 0.3953 | 0.068* | |
C2 | −0.0749 (6) | 0.5366 (3) | 0.2776 (4) | 0.0568 (9) | |
H2C | −0.1067 | 0.4794 | 0.2172 | 0.068* | |
C3 | 0.1172 (6) | 0.6057 (3) | 0.2633 (3) | 0.0501 (9) | |
H3B | 0.2206 | 0.5942 | 0.1941 | 0.060* | |
C4 | 0.1560 (6) | 0.6916 (2) | 0.3512 (3) | 0.0424 (8) | |
C5 | 0.0006 (6) | 0.7027 (3) | 0.4547 (3) | 0.0468 (8) | |
H5A | 0.0259 | 0.7599 | 0.5158 | 0.056* | |
C6 | 0.3564 (5) | 0.7710 (2) | 0.3388 (3) | 0.0406 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0685 (16) | 0.0605 (15) | 0.0481 (13) | −0.0083 (13) | 0.0346 (11) | 0.0048 (12) |
N1 | 0.0523 (17) | 0.0572 (17) | 0.0510 (16) | 0.0048 (15) | 0.0278 (13) | 0.0007 (15) |
N2 | 0.071 (2) | 0.0523 (17) | 0.0416 (16) | −0.0005 (15) | 0.0278 (14) | 0.0007 (14) |
N3 | 0.0516 (16) | 0.0485 (16) | 0.0433 (15) | 0.0003 (13) | 0.0275 (12) | 0.0037 (12) |
C1 | 0.055 (2) | 0.058 (2) | 0.059 (2) | −0.0029 (18) | 0.0205 (18) | 0.0033 (18) |
C2 | 0.073 (2) | 0.0444 (19) | 0.056 (2) | −0.0005 (19) | 0.0236 (18) | −0.0053 (17) |
C3 | 0.062 (2) | 0.052 (2) | 0.0397 (17) | 0.0036 (18) | 0.0284 (16) | 0.0020 (15) |
C4 | 0.0523 (19) | 0.0395 (17) | 0.0384 (16) | 0.0085 (15) | 0.0235 (14) | 0.0056 (13) |
C5 | 0.0506 (18) | 0.0514 (19) | 0.0417 (17) | 0.0002 (17) | 0.0247 (15) | −0.0041 (15) |
C6 | 0.0460 (18) | 0.0427 (18) | 0.0355 (16) | 0.0118 (14) | 0.0194 (13) | 0.0068 (14) |
O1—N3 | 1.423 (3) | C1—H1B | 0.9300 |
O1—H1A | 0.8200 | C2—C3 | 1.378 (4) |
N1—C1 | 1.308 (4) | C2—H2C | 0.9300 |
N1—C5 | 1.348 (4) | C3—C4 | 1.373 (4) |
N2—C6 | 1.343 (4) | C3—H3B | 0.9300 |
N2—H2A | 0.9929 | C4—C5 | 1.385 (4) |
N2—H2B | 0.9787 | C4—C6 | 1.491 (4) |
N3—C6 | 1.300 (4) | C5—H5A | 0.9300 |
C1—C2 | 1.378 (4) | ||
N3—O1—H1A | 109.5 | C4—C3—C2 | 120.0 (3) |
C1—N1—C5 | 117.5 (3) | C4—C3—H3B | 120.0 |
C6—N2—H2A | 113.5 | C2—C3—H3B | 120.0 |
C6—N2—H2B | 125.8 | C3—C4—C5 | 117.4 (3) |
H2A—N2—H2B | 93.5 | C3—C4—C6 | 122.6 (3) |
C6—N3—O1 | 108.1 (2) | C5—C4—C6 | 119.9 (3) |
N1—C1—C2 | 124.0 (3) | N1—C5—C4 | 123.2 (3) |
N1—C1—H1B | 118.0 | N1—C5—H5A | 118.4 |
C2—C1—H1B | 118.0 | C4—C5—H5A | 118.4 |
C3—C2—C1 | 117.9 (3) | N3—C6—N2 | 125.5 (3) |
C3—C2—H2C | 121.1 | N3—C6—C4 | 115.5 (3) |
C1—C2—H2C | 121.1 | N2—C6—C4 | 118.6 (2) |
C5—N1—C1—C2 | −0.2 (5) | C6—C4—C5—N1 | 179.3 (3) |
N1—C1—C2—C3 | 1.3 (5) | O1—N3—C6—N2 | 7.4 (4) |
C1—C2—C3—C4 | −2.1 (5) | O1—N3—C6—C4 | 179.7 (2) |
C2—C3—C4—C5 | 1.9 (5) | C3—C4—C6—N3 | 22.5 (4) |
C2—C3—C4—C6 | −178.3 (3) | C5—C4—C6—N3 | −157.7 (3) |
C1—N1—C5—C4 | 0.0 (5) | C3—C4—C6—N2 | −164.7 (3) |
C3—C4—C5—N1 | −0.9 (5) | C5—C4—C6—N2 | 15.1 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2B···N3i | 0.98 | 2.11 | 3.023 (4) | 155 |
O1—H1A···N1ii | 0.82 | 1.95 | 2.767 (4) | 176 |
N2—H2A···O1 | 0.99 | 2.13 | 2.539 (4) | 103 |
Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) x+1, −y+3/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C6H7N3O |
Mr | 137.15 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 5.5220 (11), 12.365 (3), 9.797 (2) |
β (°) | 94.38 (3) |
V (Å3) | 667.0 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.20 × 0.20 × 0.10 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.951, 0.970 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 1444, 1307, 782 |
Rint | 0.053 |
(sin θ/λ)max (Å−1) | 0.616 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.060, 0.158, 1.16 |
No. of reflections | 1307 |
No. of parameters | 93 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 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).
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2B···N3i | 0.98 | 2.11 | 3.023 (4) | 155 |
O1—H1A···N1ii | 0.82 | 1.95 | 2.767 (4) | 176 |
N2—H2A···O1 | 0.99 | 2.13 | 2.539 (4) | 103 |
Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) x+1, −y+3/2, z−1/2. |
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,