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In the crystal structure of the title compound, C
7H
8N
2O
3, molecules form centrosymmetrical dimers
via N—H
O hydrogen bonds.
Supporting information
CCDC reference: 234866
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.043
- wR factor = 0.111
- Data-to-parameter ratio = 12.9
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for N5 - C5 = 6.45 su
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
0 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
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; 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: ORTEP-3 for Windows (Farrugia, 1997) and PLUTON97 (Spek, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
4,6-Dimethyl-5-nitro-1
H-pyridin-2-one
top
Crystal data top
C7H8N2O3 | F(000) = 352 |
Mr = 168.15 | Dx = 1.443 Mg m−3 |
Monoclinic, P21/n | Melting point: 518 K |
Hall symbol: -P 2yn | Cu Kα radiation, λ = 1.5418 Å |
a = 9.7677 (15) Å | Cell parameters from 25 reflections |
b = 5.875 (3) Å | θ = 28–31° |
c = 13.7295 (15) Å | µ = 0.98 mm−1 |
β = 100.76 (1)° | T = 293 K |
V = 774.0 (4) Å3 | Needle, colourless |
Z = 4 | 0.3 × 0.1 × 0.03 mm |
Data collection top
Enraf–Nonius CAD-4 diffractometer | Rint = 0.037 |
Radiation source: fine-focus sealed tube | θmax = 69.9°, θmin = 5.1° |
Graphite monochromator | h = −11→11 |
non–profiled ω scans | k = 0→7 |
1524 measured reflections | l = 0→16 |
1462 independent reflections | 1 standard reflections every 200 reflections |
999 reflections with I > 2σ(I) | intensity decay: none |
Refinement top
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.111 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.98 | w = 1/[σ2(Fo2) + (0.0554P)2] where P = (Fo2 + 2Fc2)/3 |
1462 reflections | (Δ/σ)max < 0.001 |
113 parameters | Δρmax = 0.13 e Å−3 |
0 restraints | Δρmin = −0.15 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.42744 (16) | 0.2535 (3) | 0.54759 (12) | 0.0423 (4) | |
H1 | 0.409 (2) | 0.149 (3) | 0.5053 (16) | 0.038 (6)* | |
C2 | 0.5533 (2) | 0.2301 (4) | 0.61175 (15) | 0.0453 (5) | |
O2 | 0.63546 (15) | 0.0769 (3) | 0.59845 (12) | 0.0605 (5) | |
C3 | 0.5763 (2) | 0.3920 (4) | 0.69052 (15) | 0.0471 (5) | |
H3 | 0.6599 | 0.3861 | 0.7358 | 0.056* | |
C4 | 0.48220 (19) | 0.5537 (4) | 0.70259 (14) | 0.0434 (5) | |
C41 | 0.5126 (2) | 0.7113 (4) | 0.78987 (17) | 0.0579 (6) | |
H41A | 0.5935 | 0.6587 | 0.8350 | 0.087* | |
H41B | 0.4343 | 0.7143 | 0.8230 | 0.087* | |
H41C | 0.5294 | 0.8618 | 0.7675 | 0.087* | |
C5 | 0.35407 (19) | 0.5590 (3) | 0.63226 (15) | 0.0414 (5) | |
N5 | 0.25012 (18) | 0.7322 (3) | 0.63966 (13) | 0.0507 (5) | |
O51 | 0.29106 (18) | 0.9246 (3) | 0.66441 (15) | 0.0732 (6) | |
O52 | 0.12725 (17) | 0.6816 (3) | 0.62211 (15) | 0.0770 (6) | |
C6 | 0.32700 (18) | 0.4046 (3) | 0.55577 (14) | 0.0404 (5) | |
C61 | 0.1974 (2) | 0.3875 (4) | 0.47778 (16) | 0.0553 (6) | |
H61A | 0.2194 | 0.3168 | 0.4196 | 0.083* | |
H61B | 0.1608 | 0.5372 | 0.4614 | 0.083* | |
H61C | 0.1292 | 0.2976 | 0.5025 | 0.083* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0472 (9) | 0.0433 (10) | 0.0360 (9) | −0.0007 (8) | 0.0065 (7) | −0.0077 (8) |
C2 | 0.0443 (9) | 0.0500 (13) | 0.0418 (11) | 0.0007 (10) | 0.0089 (8) | −0.0035 (10) |
O2 | 0.0526 (8) | 0.0650 (11) | 0.0604 (10) | 0.0147 (8) | 0.0011 (7) | −0.0190 (8) |
C3 | 0.0472 (10) | 0.0532 (14) | 0.0396 (11) | −0.0010 (10) | 0.0049 (8) | −0.0062 (10) |
C4 | 0.0470 (10) | 0.0457 (12) | 0.0392 (11) | −0.0057 (9) | 0.0124 (8) | −0.0032 (9) |
C41 | 0.0642 (13) | 0.0574 (15) | 0.0502 (13) | −0.0001 (12) | 0.0061 (10) | −0.0162 (12) |
C5 | 0.0447 (9) | 0.0393 (11) | 0.0425 (11) | 0.0004 (9) | 0.0140 (8) | 0.0006 (9) |
N5 | 0.0537 (10) | 0.0472 (11) | 0.0533 (11) | −0.0009 (9) | 0.0155 (8) | −0.0002 (9) |
O51 | 0.0757 (11) | 0.0493 (10) | 0.0957 (15) | 0.0033 (9) | 0.0189 (10) | −0.0044 (10) |
O52 | 0.0535 (9) | 0.0799 (13) | 0.0984 (15) | 0.0047 (9) | 0.0163 (9) | −0.0117 (11) |
C6 | 0.0434 (9) | 0.0404 (11) | 0.0382 (11) | −0.0004 (9) | 0.0098 (8) | 0.0048 (9) |
C61 | 0.0525 (11) | 0.0633 (16) | 0.0473 (13) | 0.0037 (11) | 0.0023 (9) | −0.0030 (11) |
Geometric parameters (Å, º) top
N1—C6 | 1.343 (2) | C41—H41B | 0.96 |
N1—C2 | 1.379 (2) | C41—H41C | 0.96 |
N1—H1 | 0.84 (2) | C5—C6 | 1.375 (3) |
C2—O2 | 1.242 (2) | C5—N5 | 1.454 (3) |
C2—C3 | 1.426 (3) | N5—O52 | 1.216 (2) |
C3—C4 | 1.353 (3) | N5—O51 | 1.226 (2) |
C3—H3 | 0.93 | C6—C61 | 1.501 (3) |
C4—C5 | 1.431 (3) | C61—H61A | 0.96 |
C4—C41 | 1.499 (3) | C61—H61B | 0.96 |
C41—H41A | 0.96 | C61—H61C | 0.96 |
| | | |
C6—N1—C2 | 126.17 (19) | H41B—C41—H41C | 109.5 |
C6—N1—H1 | 118.4 (13) | C6—C5—C4 | 121.33 (18) |
C2—N1—H1 | 114.7 (13) | C6—C5—N5 | 118.52 (17) |
O2—C2—N1 | 120.11 (19) | C4—C5—N5 | 120.14 (18) |
O2—C2—C3 | 125.47 (18) | O52—N5—O51 | 122.6 (2) |
N1—C2—C3 | 114.41 (19) | O52—N5—C5 | 119.40 (19) |
C4—C3—C2 | 123.15 (19) | O51—N5—C5 | 117.95 (18) |
C4—C3—H3 | 118.4 | N1—C6—C5 | 117.41 (17) |
C2—C3—H3 | 118.4 | N1—C6—C61 | 115.33 (18) |
C3—C4—C5 | 117.44 (19) | C5—C6—C61 | 127.25 (18) |
C3—C4—C41 | 119.59 (18) | C6—C61—H61A | 109.5 |
C5—C4—C41 | 122.91 (19) | C6—C61—H61B | 109.5 |
C4—C41—H41A | 109.5 | H61A—C61—H61B | 109.5 |
C4—C41—H41B | 109.5 | C6—C61—H61C | 109.5 |
H41A—C41—H41B | 109.5 | H61A—C61—H61C | 109.5 |
C4—C41—H41C | 109.5 | H61B—C61—H61C | 109.5 |
H41A—C41—H41C | 109.5 | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.84 (2) | 1.94 (2) | 2.776 (2) | 176 (2) |
C61—H61B···O52 | 0.96 | 2.44 | 2.809 (3) | 102 |
Symmetry code: (i) −x+1, −y, −z+1. |
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