In the title compound, C
9H
8N
2O
4, the 3-nitrobenzaldehyde oxime and acetyl group have a dihedral angle of 19.5 (4)°. The acetyl carbonyl and 3-nitrobenzaldehyde oxime groups both adopt a
trans configuration (
E). In the crystal structure, molecules are linked by a series of weak intermolecular C—H
O interactions, forming a sheet-like structure parallel to the (303) plane.
Supporting information
CCDC reference: 248860
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.061
- wR factor = 0.158
- Data-to-parameter ratio = 12.4
checkCIF/PLATON results
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No errors found in this datablock
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXL97 and WinGX2003 (Farrugia, 1999).
(
E)-3-Nitrobenzaldehyde
O-acetyloxime
top
Crystal data top
C9H8N2O4 | F(000) = 432 |
Mr = 208.17 | Dx = 1.443 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 600 reflections |
a = 8.3129 (11) Å | θ = 20.0–25.0° |
b = 11.2119 (15) Å | µ = 0.12 mm−1 |
c = 10.2947 (14) Å | T = 293 K |
β = 92.769 (2)° | Rectangular, colorless |
V = 958.4 (2) Å3 | 0.42 × 0.40 × 0.36 mm |
Z = 4 | |
Data collection top
Bruker SMART area-detector diffractometer | Rint = 0.037 |
Graphite monochromator | θmax = 25.0°, θmin = 2.5° |
φ and ω scans | h = −9→9 |
9042 measured reflections | k = −13→13 |
1688 independent reflections | l = −12→12 |
1386 reflections with I > 2σ(I) | |
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)] = 0.061 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.158 | H-atom parameters constrained |
S = 1.12 | w = 1/[σ2(Fo2) + (0.0771P)2 + 0.3126P] where P = (Fo2 + 2Fc2)/3 |
1688 reflections | (Δ/σ)max < 0.001 |
136 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All e.s.d.'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 | x | y | z | Uiso*/Ueq | |
O9 | −0.0503 (2) | 0.11306 (14) | 0.33827 (16) | 0.0502 (6) | |
O10 | −0.1473 (3) | 0.29506 (17) | 0.3809 (2) | 0.0701 (8) | |
O12 | 0.4967 (3) | 0.0201 (2) | −0.2923 (2) | 0.0917 (10) | |
O13 | 0.3906 (3) | −0.11684 (18) | −0.1806 (2) | 0.0678 (8) | |
N8 | 0.0347 (3) | 0.16903 (18) | 0.2374 (2) | 0.0494 (7) | |
N12 | 0.4197 (3) | −0.0126 (2) | −0.2018 (2) | 0.0537 (8) | |
C1 | 0.2036 (3) | 0.1273 (2) | 0.0663 (2) | 0.0413 (8) | |
C2 | 0.2467 (3) | 0.2471 (2) | 0.0493 (2) | 0.0468 (8) | |
C3 | 0.3453 (3) | 0.2790 (2) | −0.0478 (3) | 0.0525 (9) | |
C4 | 0.4042 (3) | 0.1950 (2) | −0.1303 (2) | 0.0498 (8) | |
C5 | 0.3598 (3) | 0.0785 (2) | −0.1133 (2) | 0.0423 (8) | |
C6 | 0.2614 (3) | 0.0422 (2) | −0.0165 (2) | 0.0411 (7) | |
C7 | 0.1016 (3) | 0.0910 (2) | 0.1711 (2) | 0.0452 (8) | |
C10 | −0.1345 (3) | 0.1931 (2) | 0.4079 (3) | 0.0475 (8) | |
C11 | −0.2065 (3) | 0.1321 (3) | 0.5191 (3) | 0.0619 (10) | |
H2 | 0.20808 | 0.30517 | 0.10424 | 0.0563* | |
H3 | 0.37278 | 0.35879 | −0.05793 | 0.0630* | |
H4 | 0.47200 | 0.21653 | −0.19568 | 0.0597* | |
H6 | 0.23464 | −0.03779 | −0.00722 | 0.0494* | |
H7 | 0.08647 | 0.01052 | 0.18867 | 0.0543* | |
H11A | −0.26515 | 0.18891 | 0.56810 | 0.0929* | |
H11B | −0.12255 | 0.09726 | 0.57406 | 0.0929* | |
H11C | −0.27842 | 0.07063 | 0.48709 | 0.0929* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O9 | 0.0588 (11) | 0.0421 (9) | 0.0518 (10) | 0.0054 (8) | 0.0246 (8) | 0.0024 (8) |
O10 | 0.0931 (16) | 0.0434 (11) | 0.0770 (14) | 0.0102 (10) | 0.0379 (12) | −0.0025 (10) |
O12 | 0.127 (2) | 0.0840 (16) | 0.0696 (14) | 0.0052 (14) | 0.0603 (14) | −0.0026 (12) |
O13 | 0.0803 (14) | 0.0528 (12) | 0.0722 (13) | 0.0025 (10) | 0.0222 (11) | −0.0139 (10) |
N8 | 0.0544 (13) | 0.0441 (12) | 0.0512 (12) | 0.0029 (10) | 0.0181 (10) | 0.0030 (10) |
N12 | 0.0558 (14) | 0.0575 (14) | 0.0487 (13) | 0.0052 (11) | 0.0123 (11) | −0.0044 (11) |
C1 | 0.0394 (13) | 0.0433 (13) | 0.0412 (13) | 0.0025 (10) | 0.0033 (10) | 0.0002 (11) |
C2 | 0.0503 (14) | 0.0404 (13) | 0.0503 (15) | 0.0025 (11) | 0.0072 (12) | −0.0026 (11) |
C3 | 0.0593 (16) | 0.0401 (13) | 0.0587 (16) | −0.0056 (12) | 0.0090 (13) | 0.0061 (12) |
C4 | 0.0523 (15) | 0.0522 (15) | 0.0457 (14) | −0.0031 (12) | 0.0115 (12) | 0.0062 (12) |
C5 | 0.0430 (13) | 0.0473 (14) | 0.0370 (12) | 0.0022 (11) | 0.0050 (10) | −0.0019 (11) |
C6 | 0.0447 (13) | 0.0377 (12) | 0.0413 (13) | −0.0002 (10) | 0.0063 (10) | 0.0008 (10) |
C7 | 0.0504 (14) | 0.0404 (13) | 0.0454 (13) | 0.0030 (11) | 0.0080 (11) | 0.0010 (11) |
C10 | 0.0500 (14) | 0.0420 (14) | 0.0513 (15) | 0.0015 (11) | 0.0094 (11) | −0.0076 (12) |
C11 | 0.0660 (18) | 0.0620 (18) | 0.0597 (17) | 0.0007 (14) | 0.0232 (14) | −0.0005 (14) |
Geometric parameters (Å, º) top
O9—N8 | 1.429 (3) | C4—C5 | 1.371 (3) |
O9—C10 | 1.363 (3) | C5—C6 | 1.381 (3) |
O10—C10 | 1.180 (3) | C10—C11 | 1.484 (4) |
O12—N12 | 1.212 (3) | C2—H2 | 0.9297 |
O13—N12 | 1.215 (3) | C3—H3 | 0.9304 |
N8—C7 | 1.256 (3) | C4—H4 | 0.9304 |
N12—C5 | 1.471 (3) | C6—H6 | 0.9300 |
C1—C2 | 1.403 (3) | C7—H7 | 0.9300 |
C1—C6 | 1.381 (3) | C11—H11A | 0.9600 |
C1—C7 | 1.462 (3) | C11—H11B | 0.9600 |
C2—C3 | 1.370 (4) | C11—H11C | 0.9602 |
C3—C4 | 1.374 (3) | | |
| | | |
O9···O13i | 3.193 (3) | C2···C10viii | 3.488 (4) |
O10···C7ii | 3.385 (3) | C3···N8viii | 3.368 (4) |
O10···N8 | 2.585 (3) | C4···O13ix | 3.387 (3) |
O10···C6ii | 3.264 (3) | C4···C2viii | 3.549 (3) |
O13···C10i | 3.203 (4) | C6···O10v | 3.264 (3) |
O13···C4iii | 3.387 (3) | C6···N12vii | 3.408 (3) |
O13···O9i | 3.193 (3) | C7···O10v | 3.385 (3) |
O9···H11Biv | 2.8835 | C10···O13i | 3.203 (4) |
O10···H7ii | 2.5767 | C10···C2vi | 3.488 (4) |
O10···H6ii | 2.4128 | H2···N8 | 2.5451 |
O12···H11Ci | 2.8279 | H3···O12ix | 2.6433 |
O12···H3iii | 2.6433 | H4···O12 | 2.4293 |
O12···H4 | 2.4293 | H4···O13ix | 2.5608 |
O13···H6 | 2.4240 | H6···O13 | 2.4240 |
O13···H11Av | 2.6998 | H6···H7 | 2.4733 |
O13···H4iii | 2.5608 | H6···O10v | 2.4128 |
N8···O10 | 2.585 (3) | H7···H6 | 2.4733 |
N8···C3vi | 3.368 (4) | H7···O10v | 2.5767 |
N12···C6vii | 3.408 (3) | H11A···O13ii | 2.6998 |
N8···H2 | 2.5451 | H11B···O9iv | 2.8835 |
C2···C4vi | 3.549 (3) | H11C···O12i | 2.8279 |
| | | |
N8—O9—C10 | 112.18 (17) | O10—C10—C11 | 126.4 (3) |
O9—N8—C7 | 109.66 (19) | C1—C2—H2 | 119.78 |
O12—N12—O13 | 123.1 (2) | C3—C2—H2 | 119.82 |
O12—N12—C5 | 118.2 (2) | C2—C3—H3 | 119.43 |
O13—N12—C5 | 118.7 (2) | C4—C3—H3 | 119.54 |
C2—C1—C6 | 119.1 (2) | C3—C4—H4 | 121.04 |
C2—C1—C7 | 121.3 (2) | C5—C4—H4 | 121.05 |
C6—C1—C7 | 119.6 (2) | C1—C6—H6 | 120.71 |
C1—C2—C3 | 120.4 (2) | C5—C6—H6 | 120.75 |
C2—C3—C4 | 121.0 (2) | N8—C7—H7 | 120.17 |
C3—C4—C5 | 117.9 (2) | C1—C7—H7 | 120.16 |
N12—C5—C4 | 118.8 (2) | C10—C11—H11A | 109.48 |
N12—C5—C6 | 118.2 (2) | C10—C11—H11B | 109.47 |
C4—C5—C6 | 123.1 (2) | C10—C11—H11C | 109.49 |
C1—C6—C5 | 118.5 (2) | H11A—C11—H11B | 109.48 |
N8—C7—C1 | 119.7 (2) | H11A—C11—H11C | 109.45 |
O9—C10—O10 | 123.8 (3) | H11B—C11—H11C | 109.45 |
O9—C10—C11 | 109.8 (2) | | |
| | | |
C10—O9—N8—C7 | −175.8 (2) | C2—C1—C7—N8 | 8.9 (4) |
N8—O9—C10—C11 | −174.3 (2) | C2—C1—C6—C5 | 0.0 (3) |
N8—O9—C10—O10 | 6.3 (4) | C6—C1—C7—N8 | −172.2 (2) |
O9—N8—C7—C1 | −176.6 (2) | C7—C1—C6—C5 | −178.9 (2) |
O13—N12—C5—C6 | −5.5 (4) | C1—C2—C3—C4 | −0.1 (4) |
O13—N12—C5—C4 | 174.4 (2) | C2—C3—C4—C5 | 0.7 (4) |
O12—N12—C5—C6 | 174.9 (2) | C3—C4—C5—C6 | −1.0 (4) |
O12—N12—C5—C4 | −5.2 (4) | C3—C4—C5—N12 | 179.1 (2) |
C6—C1—C2—C3 | −0.3 (4) | C4—C5—C6—C1 | 0.7 (4) |
C7—C1—C2—C3 | 178.6 (2) | N12—C5—C6—C1 | −179.5 (2) |
Symmetry codes: (i) −x, −y, −z; (ii) −x, y+1/2, −z+1/2; (iii) −x+1, y−1/2, −z−1/2; (iv) −x, −y, −z+1; (v) −x, y−1/2, −z+1/2; (vi) x, −y+1/2, z+1/2; (vii) −x+1, −y, −z; (viii) x, −y+1/2, z−1/2; (ix) −x+1, y+1/2, −z−1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···O13ix | 0.93 | 2.56 | 3.387 (3) | 148 |
C6—H6···O10v | 0.93 | 2.41 | 3.264 (3) | 152 |
C7—H7···O10v | 0.93 | 2.58 | 3.385 (3) | 146 |
Symmetry codes: (v) −x, y−1/2, −z+1/2; (ix) −x+1, y+1/2, −z−1/2. |