N-Ethyl-3,5-dinitro­benzamide

Xu, J.-Y.; Cheng, W.-H.

doi:10.1107/S160053681100804X

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o822

doi:10.1107/S160053681100804X

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N-Ethyl-3,5-dinitrobenzamide

Jia-Ying Xu ^a ^* and Wei-Hua Cheng ^b

^aCollege of Chemical and Biological Engineering, Yancheng Institute of Technology, Yinbing Road No. 9 Yancheng, Yancheng 224051, People's Republic of China, and ^bDepartment of Chemical Engineering, Yancheng College of Textile Technology, Yancheng 224051, People's Republic of China
^*Correspondence e-mail: xujiaying-1984@163.com

(Received 24 February 2011; accepted 3 March 2011; online 9 March 2011)

In the title molecule, C₉H₉N₃O₅, the dihedral angle between the mean planes of the amide group and the benzene ring is 31.24 (14)°. In the crystal, N—H⋯O hydrogen bonds link the molecules to form one-dimensional chains propagating in [100].

Related literature

For the synthesis of the title compound, see: Lee et al. (2009 ). For standard bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₉H₉N₃O₅
M_r = 239.19
Triclinic, $[P \overline 1]$
a = 4.854 (1) Å
b = 10.488 (2) Å
c = 10.851 (2) Å
α = 101.49 (3)°
β = 97.84 (3)°
γ = 95.25 (3)°
V = 532.26 (19) Å³
Z = 2
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 293 K
0.20 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.976, T_max = 0.988
2203 measured reflections
1955 independent reflections
1321 reflections with I > 2σ(I)
R_int = 0.021
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.161
S = 1.01
1955 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O5ⁱ	0.86	2.13	2.886 (3)	146
Symmetry code: (i) x+1, y, z.

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo,1995 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681100804X/su2259sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681100804X/su2259Isup2.hkl

checkCIF report

Comment top

The title compound is an important organic intermediate, and such amide derivatives exhibit biological activities, such as antibacterial and antifungal effects (Lee et al., 2009). Herein we report on the crystal structure of the title substitued benzamide compound.

The molecular structure of the title compound is illustrated in Fig. 1. The bond lengths and angles are within normal ranges (Allen et al., 1987). The dihedral angle between the amide group [atoms O5,N3,C7,C8, planar to within 0.012 Å] and the benzene ring (C1-C6) is 31.24 (14) °.

In the crystal of the title compound molecules are connected via N—H···O intermolecular hydrogen bonds (Table 1), to form a one-dimensional polymer propagating in [100]. These chains stack along the c axis direction.

Related literature top

For the synthesis of the title compound, see: Lee et al. (2009). For standard bond-length data, see: Allen et al. (1987).

Experimental top

The title compound was prepared following a literature proceedure (Lee et al., 2009). Crystals, suitable for X-ray diffraction analysis, were obtained by slow evaporation, over a period of 5 days, of a solution of the title compound in ethanol [0.2 g, 0.84 mmol in 25 ml ethanol].

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software (Enraf–Nonius, 1985); data reduction: XCAD4 (Harms & Wocadlo,1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title molecule, with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. A view of the crystal packing of the title compound. The N—H···O hydrogen bonds are shown as dashed lines.

N-Ethyl-3,5-dinitrobenzamide top

Crystal data top

C₉H₉N₃O₅	Z = 2
M_r = 239.19	F(000) = 248
Triclinic, P1	D_x = 1.492 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.854 (1) Å	Cell parameters from 25 reflections
b = 10.488 (2) Å	θ = 10–13°
c = 10.851 (2) Å	µ = 0.12 mm⁻¹
α = 101.49 (3)°	T = 293 K
β = 97.84 (3)°	Block, colourless
γ = 95.25 (3)°	0.20 × 0.10 × 0.10 mm
V = 532.26 (19) Å³

Data collection top

Enraf–Nonius CAD-4 diffractometer	1321 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.021
Graphite monochromator	θ_max = 25.4°, θ_min = 1.9°
ω/2θ scans	h = 0→5
Absorption correction: ψ scan (North et al., 1968)	k = −12→12
T_min = 0.976, T_max = 0.988	l = −13→12
2203 measured reflections	3 standard reflections every 200 reflections
1955 independent reflections	intensity decay: 1%

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.161	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.090P)²] where P = (F_o² + 2F_c²)/3
1955 reflections	(Δ/σ)_max < 0.001
154 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₉H₉N₃O₅	γ = 95.25 (3)°
M_r = 239.19	V = 532.26 (19) Å³
Triclinic, P1	Z = 2
a = 4.854 (1) Å	Mo Kα radiation
b = 10.488 (2) Å	µ = 0.12 mm⁻¹
c = 10.851 (2) Å	T = 293 K
α = 101.49 (3)°	0.20 × 0.10 × 0.10 mm
β = 97.84 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1321 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.021
T_min = 0.976, T_max = 0.988	3 standard reflections every 200 reflections
2203 measured reflections	intensity decay: 1%
1955 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.161	H-atom parameters constrained
S = 1.01	Δρ_max = 0.15 e Å⁻³
1955 reflections	Δρ_min = −0.23 e Å⁻³
154 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

	x	y	z	U_iso*/U_eq
C1	0.1490 (5)	0.7075 (2)	0.2465 (2)	0.0428 (6)
H1A	−0.0017	0.6473	0.2494	0.051*
N1	0.0031 (5)	0.6713 (2)	0.0152 (2)	0.0617 (6)
O1	0.0675 (6)	0.6862 (3)	−0.0856 (2)	0.0985 (9)
N2	0.8248 (5)	0.9842 (2)	0.2289 (3)	0.0576 (6)
C2	0.1956 (5)	0.7377 (2)	0.1327 (2)	0.0454 (6)
O2	−0.2072 (5)	0.6034 (2)	0.02613 (19)	0.0795 (7)
N3	0.4868 (4)	0.7427 (2)	0.57021 (18)	0.0453 (5)
H3A	0.6513	0.7677	0.5563	0.054*
C3	0.4127 (5)	0.8280 (2)	0.1236 (2)	0.0492 (6)
H3B	0.4392	0.8480	0.0459	0.059*
O3	0.8469 (5)	1.0119 (2)	0.1269 (2)	0.0911 (8)
C4	0.5890 (5)	0.8874 (2)	0.2352 (2)	0.0449 (6)
O4	0.9911 (4)	1.0292 (2)	0.3254 (2)	0.0743 (6)
O5	0.0241 (3)	0.70717 (19)	0.49151 (17)	0.0574 (5)
C5	0.5555 (5)	0.8591 (2)	0.3510 (2)	0.0414 (6)
H5A	0.6803	0.8997	0.4241	0.050*
C6	0.3318 (4)	0.7688 (2)	0.3573 (2)	0.0388 (5)
C7	0.2693 (4)	0.7366 (2)	0.4798 (2)	0.0408 (6)
C8	0.4582 (5)	0.7087 (2)	0.6918 (2)	0.0497 (6)
H8A	0.2783	0.7293	0.7144	0.060*
H8B	0.6035	0.7612	0.7572	0.060*
C9	0.4794 (7)	0.5668 (3)	0.6881 (3)	0.0712 (9)
H9A	0.4582	0.5484	0.7697	0.107*
H9B	0.6592	0.5465	0.6680	0.107*
H9C	0.3345	0.5145	0.6242	0.107*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0323 (12)	0.0467 (13)	0.0504 (14)	0.0078 (10)	0.0086 (10)	0.0101 (11)
N1	0.0608 (16)	0.0709 (16)	0.0496 (14)	0.0068 (13)	0.0017 (11)	0.0094 (11)
O1	0.113 (2)	0.131 (2)	0.0458 (13)	−0.0138 (16)	0.0034 (12)	0.0245 (13)
N2	0.0512 (14)	0.0510 (13)	0.0797 (17)	0.0095 (11)	0.0225 (13)	0.0255 (12)
C2	0.0424 (14)	0.0518 (15)	0.0425 (13)	0.0125 (11)	0.0041 (10)	0.0101 (11)
O2	0.0575 (13)	0.1052 (18)	0.0627 (13)	−0.0106 (12)	−0.0020 (10)	0.0039 (12)
N3	0.0292 (10)	0.0650 (13)	0.0446 (11)	0.0026 (9)	0.0098 (8)	0.0172 (9)
C3	0.0528 (15)	0.0544 (15)	0.0489 (14)	0.0174 (12)	0.0161 (12)	0.0207 (12)
O3	0.0941 (18)	0.1021 (18)	0.0914 (17)	−0.0079 (14)	0.0313 (14)	0.0522 (14)
C4	0.0396 (13)	0.0423 (13)	0.0586 (15)	0.0087 (10)	0.0153 (11)	0.0176 (11)
O4	0.0597 (13)	0.0651 (13)	0.0940 (16)	−0.0137 (10)	0.0088 (12)	0.0193 (11)
O5	0.0287 (9)	0.0861 (14)	0.0596 (11)	0.0045 (8)	0.0149 (8)	0.0164 (9)
C5	0.0330 (12)	0.0439 (13)	0.0489 (13)	0.0095 (10)	0.0090 (10)	0.0098 (11)
C6	0.0287 (11)	0.0446 (13)	0.0458 (13)	0.0100 (10)	0.0090 (9)	0.0114 (10)
C7	0.0270 (12)	0.0501 (14)	0.0468 (13)	0.0074 (10)	0.0115 (10)	0.0089 (10)
C8	0.0454 (14)	0.0633 (17)	0.0415 (14)	0.0050 (12)	0.0099 (11)	0.0125 (12)
C9	0.089 (2)	0.0671 (19)	0.0588 (18)	0.0082 (17)	0.0087 (16)	0.0185 (15)

Geometric parameters (Å, º) top

C1—C2	1.376 (3)	C3—C4	1.380 (4)
C1—C6	1.394 (3)	C3—H3B	0.9300
C1—H1A	0.9300	C4—C5	1.375 (3)
N1—O1	1.212 (3)	O5—C7	1.232 (3)
N1—O2	1.224 (3)	C5—C6	1.392 (3)
N1—C2	1.479 (3)	C5—H5A	0.9300
N2—O4	1.214 (3)	C6—C7	1.498 (3)
N2—O3	1.214 (3)	C8—C9	1.494 (4)
N2—C4	1.477 (3)	C8—H8A	0.9700
C2—C3	1.379 (4)	C8—H8B	0.9700
N3—C7	1.327 (3)	C9—H9A	0.9600
N3—C8	1.454 (3)	C9—H9B	0.9600
N3—H3A	0.8600	C9—H9C	0.9600

C2—C1—C6	118.8 (2)	C4—C5—C6	119.0 (2)
C2—C1—H1A	120.6	C4—C5—H5A	120.5
C6—C1—H1A	120.6	C6—C5—H5A	120.5
O1—N1—O2	124.6 (2)	C5—C6—C1	119.7 (2)
O1—N1—C2	117.6 (2)	C5—C6—C7	123.0 (2)
O2—N1—C2	117.8 (2)	C1—C6—C7	117.3 (2)
O4—N2—O3	123.4 (2)	O5—C7—N3	124.0 (2)
O4—N2—C4	118.2 (2)	O5—C7—C6	119.2 (2)
O3—N2—C4	118.4 (3)	N3—C7—C6	116.78 (19)
C1—C2—C3	122.9 (2)	N3—C8—C9	112.1 (2)
C1—C2—N1	118.7 (2)	N3—C8—H8A	109.2
C3—C2—N1	118.5 (2)	C9—C8—H8A	109.2
C7—N3—C8	122.68 (19)	N3—C8—H8B	109.2
C7—N3—H3A	118.7	C9—C8—H8B	109.2
C8—N3—H3A	118.7	H8A—C8—H8B	107.9
C2—C3—C4	116.8 (2)	C8—C9—H9A	109.5
C2—C3—H3B	121.6	C8—C9—H9B	109.5
C4—C3—H3B	121.6	H9A—C9—H9B	109.5
C5—C4—C3	122.7 (2)	C8—C9—H9C	109.5
C5—C4—N2	118.9 (2)	H9A—C9—H9C	109.5
C3—C4—N2	118.3 (2)	H9B—C9—H9C	109.5

C6—C1—C2—C3	−1.3 (4)	C3—C4—C5—C6	−1.3 (4)
C6—C1—C2—N1	179.3 (2)	N2—C4—C5—C6	179.42 (19)
O1—N1—C2—C1	−170.8 (3)	C4—C5—C6—C1	0.9 (3)
O2—N1—C2—C1	8.0 (4)	C4—C5—C6—C7	−176.8 (2)
O1—N1—C2—C3	9.8 (4)	C2—C1—C6—C5	0.3 (3)
O2—N1—C2—C3	−171.4 (2)	C2—C1—C6—C7	178.2 (2)
C1—C2—C3—C4	0.9 (4)	C8—N3—C7—O5	3.0 (4)
N1—C2—C3—C4	−179.6 (2)	C8—N3—C7—C6	−177.4 (2)
C2—C3—C4—C5	0.4 (4)	C5—C6—C7—O5	147.8 (2)
C2—C3—C4—N2	179.7 (2)	C1—C6—C7—O5	−30.0 (3)
O4—N2—C4—C5	4.5 (3)	C5—C6—C7—N3	−31.9 (3)
O3—N2—C4—C5	−177.4 (2)	C1—C6—C7—N3	150.3 (2)
O4—N2—C4—C3	−174.8 (2)	C7—N3—C8—C9	90.0 (3)
O3—N2—C4—C3	3.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O5ⁱ	0.86	2.13	2.886 (3)	146

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₉H₉N₃O₅
M_r	239.19
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	4.854 (1), 10.488 (2), 10.851 (2)
α, β, γ (°)	101.49 (3), 97.84 (3), 95.25 (3)
V (Å³)	532.26 (19)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.20 × 0.10 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.976, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	2203, 1955, 1321
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.603

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.161, 1.01
No. of reflections	1955
No. of parameters	154
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.23

Computer programs: CAD-4 Software (Enraf–Nonius, 1985), XCAD4 (Harms & Wocadlo,1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O5ⁱ	0.86	2.13	2.886 (3)	146

Symmetry code: (i) x+1, y, z.

Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for data collection.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Enraf–Nonius (1985). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
Lee, S., Song, K. H., Choe, J., Ju, J. & Jo, Y. (2009). J. Org. Chem. 74, 6358–6361. Web of Science PubMed Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar