(E)-3-Nitro­benz­aldehyde O-acetyl­oxime

In the title compound, C₉H₈N₂O₄, 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.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](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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Computing details

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

Crystal data

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) Å^3	0.42 × 0.40 × 0.36 mm
Z = 4

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.158	H-atom parameters constrained
S = 1.12	w = 1/[σ^2(Fo^2) + (0.0771P)^2 + 0.3126P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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···O13^i	3.193 (3)	C2···C10^viii	3.488 (4)
O10···C7^ii	3.385 (3)	C3···N8^viii	3.368 (4)
O10···N8	2.585 (3)	C4···O13^ix	3.387 (3)
O10···C6^ii	3.264 (3)	C4···C2^viii	3.549 (3)
O13···C10^i	3.203 (4)	C6···O10^v	3.264 (3)
O13···C4^iii	3.387 (3)	C6···N12^vii	3.408 (3)
O13···O9^i	3.193 (3)	C7···O10^v	3.385 (3)
O9···H11B^iv	2.8835	C10···O13^i	3.203 (4)
O10···H7^ii	2.5767	C10···C2^vi	3.488 (4)
O10···H6^ii	2.4128	H2···N8	2.5451
O12···H11C^i	2.8279	H3···O12^ix	2.6433
O12···H3^iii	2.6433	H4···O12	2.4293
O12···H4	2.4293	H4···O13^ix	2.5608
O13···H6	2.4240	H6···O13	2.4240
O13···H11A^v	2.6998	H6···H7	2.4733
O13···H4^iii	2.5608	H6···O10^v	2.4128
N8···O10	2.585 (3)	H7···H6	2.4733
N8···C3^vi	3.368 (4)	H7···O10^v	2.5767
N12···C6^vii	3.408 (3)	H11A···O13^ii	2.6998
N8···H2	2.5451	H11B···O9^iv	2.8835
C2···C4^vi	3.549 (3)	H11C···O12^i	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)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O13^ix	0.93	2.56	3.387 (3)	148
C6—H6···O10^v	0.93	2.41	3.264 (3)	152
C7—H7···O10^v	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.