PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2009 September 1; 65(Pt 9): o2278.
Published online 2009 August 29. doi:  10.1107/S1600536809031997
PMCID: PMC2970120

N-Isopropyl-3-methyl-2-nitro­benzamide

Abstract

In the title compound, C11H14N2O3, the bond lengths and angles are within normal ranges. Weak inter­molecular N—H(...)O inter­actions link the mol­ecules into chains along the a axis. A non-classical intra­molecular C—H(...)O inter­action (nitro O atom and a H atom of the nearest methyl group) is found, forming a six-membered ring with a twisted conformation. This six-membered ring has a twisted conformation.

Related literature

For bond–length data, see: Allen et al. (1987 [triangle]). For general background, see: Lahm et al. (2005 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o2278-scheme1.jpg

Experimental

Crystal data

  • C11H14N2O3
  • M r = 222.24
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2278-efi1.jpg
  • a = 9.4230 (19) Å
  • b = 13.250 (3) Å
  • c = 20.041 (4) Å
  • V = 2502.2 (9) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 298 K
  • 0.30 × 0.20 × 0.10 mm

Data collection

  • Enraf–Nonius CAD-4 diffractometer
  • Absorption correction: ψ scan (North et al., 1968 [triangle]) T min = 0.974, T max = 0.991
  • 2260 measured reflections
  • 2260 independent reflections
  • 1135 reflections with I > 2σ(I)
  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement

  • R[F 2 > 2σ(F 2)] = 0.066
  • wR(F 2) = 0.174
  • S = 1.00
  • 2260 reflections
  • 146 parameters
  • H-atom parameters constrained
  • Δρmax = 0.22 e Å−3
  • Δρmin = −0.16 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 [triangle]); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809031997/rk2153sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809031997/rk2153Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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

supplementary crystallographic information

Comment

The title compound contains nitro– and acetylamino–groups, which can react with different groups to prepare various functional organic compounds as a fine organic intermediate (Lahm et al., 2005). We herein report the crystal structure.

In the title molecule (I), (Fig. 1), the bond lengths and angles are within normal ranges (Allen et al., 1987). Intramolecular C—H···O interaction (Table 1) results in the formation of a six–membered ring (O3/N2/C10/C9/C11/H11A), having twisted conformation.

In the crystal structure, weak intermolecular N—H···O interactions (Table 1) link the molecules into chains along the a axis (Fig. 2), in which they may be effective in the stabilization of the structure.

Experimental

N–isopropyl–3–methyl–2–nitrobenzamide were dissolved in DMF (50 mL). The solution was then poured to ice water. The crystalline product was isolated by filtration, washed with water (600 ml), dried and gave the product 1.8 g. The single crystals were obtained by evaporating the acetone slowly at room temperature for about 14 d.

Refinement

The H atoms were positioned geometrically, with N—H = 0.86 Å (for NH) and C—H = 0.93, 0.96 and 0.98 Å for aromatic, methyl and methine H atoms, respectively, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C), where x = 1.5 for methyl H, and x = 1.2 for other H atoms.

Figures

Fig. 1.
Asymmetric unit of the title molecular structure, with the atom–labeling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as a small spheres of arbitrary radius.
Fig. 2.
A packing diagram for (I).

Crystal data

C11H14N2O3F(000) = 944
Mr = 222.24Dx = 1.180 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 25 reflections
a = 9.4230 (19) Åθ = 10–13°
b = 13.250 (3) ŵ = 0.09 mm1
c = 20.041 (4) ÅT = 298 K
V = 2502.2 (9) Å3Needle, colourless
Z = 80.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer1135 reflections with I > 2σ(I)
Radiation source: fine–focus sealed tubeRint = 0.0000
graphiteθmax = 25.3°, θmin = 2.0°
ω/2θ scansh = 0→11
Absorption correction: ψ scan (North et al., 1968)k = 0→15
Tmin = 0.974, Tmax = 0.991l = 0→24
2260 measured reflections3 standard reflections every 200 reflections
2260 independent reflections intensity decay: 1%

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.066H-atom parameters constrained
wR(F2) = 0.174w = 1/[σ2(Fo2) + (0.06P)2 + 0.9P] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
2260 reflectionsΔρmax = 0.22 e Å3
146 parametersΔρmin = −0.16 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0059 (11)

Special details

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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)

xyzUiso*/Ueq
O10.1002 (2)0.4262 (2)0.21752 (13)0.0801 (9)
N1−0.0987 (3)0.4490 (2)0.27836 (16)0.0642 (9)
H1A−0.18810.43670.28090.077*
C10.0066 (6)0.4504 (4)0.3892 (3)0.1265 (19)
H1B0.06990.39740.37560.190*
H1C−0.07690.42150.40890.190*
H1D0.05330.49280.42120.190*
O2−0.0336 (3)0.51283 (19)0.09602 (15)0.0890 (10)
N20.0028 (3)0.4269 (2)0.08678 (16)0.0635 (8)
C2−0.1321 (5)0.5952 (3)0.3487 (2)0.1034 (16)
H2A−0.15430.63450.30990.155*
H2B−0.08710.63740.38140.155*
H2C−0.21780.56750.36700.155*
O30.1088 (3)0.4024 (2)0.05598 (16)0.1007 (11)
C3−0.0342 (4)0.5115 (3)0.32994 (19)0.0676 (11)
H3A0.05230.54150.31140.081*
C4−0.0271 (3)0.4105 (2)0.22794 (18)0.0540 (9)
C5−0.1076 (3)0.3415 (2)0.18197 (18)0.0519 (9)
C6−0.1956 (4)0.2662 (3)0.2058 (2)0.0698 (11)
H6A−0.21020.26000.25160.084*
C7−0.2619 (4)0.2004 (3)0.1630 (2)0.0793 (12)
H7A−0.32060.15000.17980.095*
C8−0.2420 (4)0.2086 (3)0.0961 (2)0.0736 (11)
H8A−0.28840.16360.06790.088*
C9−0.1545 (4)0.2819 (3)0.0684 (2)0.0642 (10)
C10−0.0889 (3)0.3463 (2)0.11363 (19)0.0540 (9)
C11−0.1371 (5)0.2899 (3)−0.0058 (2)0.0973 (15)
H11A−0.07430.3448−0.01600.146*
H11B−0.22790.3020−0.02600.146*
H11C−0.09810.2282−0.02280.146*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0298 (12)0.130 (2)0.0802 (19)−0.0125 (14)0.0014 (13)−0.0014 (17)
N10.0309 (14)0.083 (2)0.079 (2)−0.0139 (15)0.0058 (16)−0.0135 (18)
C10.146 (5)0.126 (4)0.107 (4)0.021 (4)−0.047 (4)0.009 (4)
O20.096 (2)0.0519 (16)0.119 (3)−0.0036 (16)0.0068 (18)0.0099 (17)
N20.0583 (19)0.064 (2)0.068 (2)−0.0068 (18)−0.0004 (17)−0.0036 (17)
C20.106 (4)0.079 (3)0.125 (4)0.010 (3)−0.028 (3)−0.028 (3)
O30.078 (2)0.114 (2)0.111 (2)−0.0197 (18)0.0431 (19)−0.0240 (19)
C30.053 (2)0.084 (3)0.066 (3)−0.019 (2)0.001 (2)−0.005 (2)
C40.0306 (17)0.064 (2)0.068 (2)−0.0026 (17)−0.0016 (18)0.009 (2)
C50.0355 (17)0.049 (2)0.071 (2)−0.0031 (16)0.0008 (17)0.0032 (19)
C60.058 (2)0.074 (3)0.077 (3)−0.011 (2)0.002 (2)0.005 (2)
C70.076 (3)0.065 (3)0.096 (3)−0.025 (2)−0.003 (3)0.005 (3)
C80.070 (3)0.060 (2)0.091 (3)−0.011 (2)−0.014 (3)−0.004 (2)
C90.061 (2)0.054 (2)0.078 (3)0.0006 (19)−0.003 (2)0.000 (2)
C100.0430 (19)0.046 (2)0.073 (3)0.0032 (17)0.0025 (18)0.0047 (19)
C110.115 (4)0.097 (3)0.080 (3)−0.018 (3)−0.006 (3)−0.010 (3)

Geometric parameters (Å, °)

O1—C41.235 (3)C3—H3A0.9800
N1—C41.318 (4)C4—C51.503 (4)
N1—C31.457 (4)C5—C61.382 (4)
N1—H1A0.8600C5—C101.383 (5)
C1—C31.488 (6)C6—C71.375 (5)
C1—H1B0.9600C6—H6A0.9300
C1—H1C0.9600C7—C81.357 (5)
C1—H1D0.9600C7—H7A0.9300
O2—N21.203 (3)C8—C91.391 (5)
N2—O31.218 (3)C8—H8A0.9300
N2—C101.475 (4)C9—C101.391 (5)
C2—C31.491 (5)C9—C111.499 (5)
C2—H2A0.9600C11—H11A0.9600
C2—H2B0.9600C11—H11B0.9600
C2—H2C0.9600C11—H11C0.9600
C4—N1—C3123.4 (3)N1—C4—C5116.6 (3)
C4—N1—H1A118.3C6—C5—C10116.9 (3)
C3—N1—H1A118.3C6—C5—C4122.0 (3)
C3—C1—H1B109.5C10—C5—C4120.9 (3)
C3—C1—H1C109.5C7—C6—C5120.9 (4)
H1B—C1—H1C109.5C7—C6—H6A119.5
C3—C1—H1D109.5C5—C6—H6A119.5
H1B—C1—H1D109.5C8—C7—C6120.2 (4)
H1C—C1—H1D109.5C8—C7—H7A119.9
O2—N2—O3124.3 (3)C6—C7—H7A119.9
O2—N2—C10117.5 (3)C7—C8—C9122.2 (4)
O3—N2—C10118.2 (3)C7—C8—H8A118.9
C3—C2—H2A109.5C9—C8—H8A118.9
C3—C2—H2B109.5C10—C9—C8115.6 (4)
H2A—C2—H2B109.5C10—C9—C11123.7 (4)
C3—C2—H2C109.5C8—C9—C11120.7 (4)
H2A—C2—H2C109.5C5—C10—C9124.1 (3)
H2B—C2—H2C109.5C5—C10—N2118.0 (3)
N1—C3—C1111.4 (3)C9—C10—N2117.8 (3)
N1—C3—C2110.1 (3)C9—C11—H11A109.5
C1—C3—C2111.3 (4)C9—C11—H11B109.5
N1—C3—H3A108.0H11A—C11—H11B109.5
C1—C3—H3A108.0C9—C11—H11C109.5
C2—C3—H3A108.0H11A—C11—H11C109.5
O1—C4—N1124.1 (3)H11B—C11—H11C109.5
O1—C4—C5119.3 (3)
C4—N1—C3—C1−95.0 (4)C7—C8—C9—C11−178.9 (4)
C4—N1—C3—C2141.1 (4)C6—C5—C10—C91.1 (5)
C3—N1—C4—O1−3.0 (6)C4—C5—C10—C9176.8 (3)
C3—N1—C4—C5175.6 (3)C6—C5—C10—N2179.1 (3)
O1—C4—C5—C6132.9 (4)C4—C5—C10—N2−5.2 (5)
N1—C4—C5—C6−45.8 (4)C8—C9—C10—C5−0.8 (5)
O1—C4—C5—C10−42.6 (5)C11—C9—C10—C5178.0 (4)
N1—C4—C5—C10138.7 (3)C8—C9—C10—N2−178.8 (3)
C10—C5—C6—C7−0.6 (5)C11—C9—C10—N20.0 (5)
C4—C5—C6—C7−176.3 (3)O2—N2—C10—C5−62.5 (4)
C5—C6—C7—C8−0.2 (6)O3—N2—C10—C5118.6 (4)
C6—C7—C8—C90.5 (6)O2—N2—C10—C9115.6 (4)
C7—C8—C9—C100.0 (6)O3—N2—C10—C9−63.3 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.862.002.855 (3)173
C11—H11A···O30.962.373.021 (5)124

Symmetry codes: (i) x−1/2, y, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RK2153).

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.
  • Enraf–Nonius (1994). CAD-4 EXPRESS Enraf–Nonius, Delft, The Netherlands.
  • Harms, K. & Wocadlo, S. (1995). XCAD4 University of Marburg, Germany.
  • Lahm, G. P., Selby, T. P., Freudenberger, J. H., Stevenson, T. M., Myers, B. J., Seburyamo, G., Smith, B. K., Flexner, L., Clark, C. E. & Cordova, D. (2005). Bioorg. Med. Chem. Lett.15, 4898–4906. [PubMed]
  • North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography