N-Isopropyl-3-methyl-2-nitro-benzamide.

In the title compound, C(11)H(14)N(2)O(3), the bond lengths and angles are within normal ranges. Weak inter-molecular N-H⋯O inter-actions link the mol-ecules into chains along the a axis. A non-classical intra-molecular C-H⋯O inter-action (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 ▶). For general background, see: Lahm et al. (2005 ▶).

Experimental

Crystal data

C11H14N2O3

M = 222.24

Orthorhombic,

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 ▶) 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 ▶); cell refinement: CAD-4 EXPRESS; 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.

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

C11H14N2O3	F(000) = 944
Mr = 222.24	Dx = 1.180 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 25 reflections
a = 9.4230 (19) Å	θ = 10–13°
b = 13.250 (3) Å	µ = 0.09 mm−1
c = 20.041 (4) Å	T = 298 K
V = 2502.2 (9) Å3	Needle, colourless
Z = 8	0.30 × 0.20 × 0.10 mm

Enraf–Nonius CAD-4 diffractometer	1135 reflections with I > 2σ(I)
Radiation source: fine–focus sealed tube	Rint = 0.0000
graphite	θmax = 25.3°, θmin = 2.0°
ω/2θ scans	h = 0→11
Absorption correction: ψ scan (North et al., 1968)	k = 0→15
Tmin = 0.974, Tmax = 0.991	l = 0→24
2260 measured reflections	3 standard reflections every 200 reflections
2260 independent reflections	intensity decay: 1%

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

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.

	x	y	z	Uiso*/Ueq
O1	0.1002 (2)	0.4262 (2)	0.21752 (13)	0.0801 (9)
N1	−0.0987 (3)	0.4490 (2)	0.27836 (16)	0.0642 (9)
H1A	−0.1881	0.4367	0.2809	0.077*
C1	0.0066 (6)	0.4504 (4)	0.3892 (3)	0.1265 (19)
H1B	0.0699	0.3974	0.3756	0.190*
H1C	−0.0769	0.4215	0.4089	0.190*
H1D	0.0533	0.4928	0.4212	0.190*
O2	−0.0336 (3)	0.51283 (19)	0.09602 (15)	0.0890 (10)
N2	0.0028 (3)	0.4269 (2)	0.08678 (16)	0.0635 (8)
C2	−0.1321 (5)	0.5952 (3)	0.3487 (2)	0.1034 (16)
H2A	−0.1543	0.6345	0.3099	0.155*
H2B	−0.0871	0.6374	0.3814	0.155*
H2C	−0.2178	0.5675	0.3670	0.155*
O3	0.1088 (3)	0.4024 (2)	0.05598 (16)	0.1007 (11)
C3	−0.0342 (4)	0.5115 (3)	0.32994 (19)	0.0676 (11)
H3A	0.0523	0.5415	0.3114	0.081*
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	−0.2102	0.2600	0.2516	0.084*
C7	−0.2619 (4)	0.2004 (3)	0.1630 (2)	0.0793 (12)
H7A	−0.3206	0.1500	0.1798	0.095*
C8	−0.2420 (4)	0.2086 (3)	0.0961 (2)	0.0736 (11)
H8A	−0.2884	0.1636	0.0679	0.088*
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	−0.0743	0.3448	−0.0160	0.146*
H11B	−0.2279	0.3020	−0.0260	0.146*
H11C	−0.0981	0.2282	−0.0228	0.146*

	U11	U22	U33	U12	U13	U23
O1	0.0298 (12)	0.130 (2)	0.0802 (19)	−0.0125 (14)	0.0014 (13)	−0.0014 (17)
N1	0.0309 (14)	0.083 (2)	0.079 (2)	−0.0139 (15)	0.0058 (16)	−0.0135 (18)
C1	0.146 (5)	0.126 (4)	0.107 (4)	0.021 (4)	−0.047 (4)	0.009 (4)
O2	0.096 (2)	0.0519 (16)	0.119 (3)	−0.0036 (16)	0.0068 (18)	0.0099 (17)
N2	0.0583 (19)	0.064 (2)	0.068 (2)	−0.0068 (18)	−0.0004 (17)	−0.0036 (17)
C2	0.106 (4)	0.079 (3)	0.125 (4)	0.010 (3)	−0.028 (3)	−0.028 (3)
O3	0.078 (2)	0.114 (2)	0.111 (2)	−0.0197 (18)	0.0431 (19)	−0.0240 (19)
C3	0.053 (2)	0.084 (3)	0.066 (3)	−0.019 (2)	0.001 (2)	−0.005 (2)
C4	0.0306 (17)	0.064 (2)	0.068 (2)	−0.0026 (17)	−0.0016 (18)	0.009 (2)
C5	0.0355 (17)	0.049 (2)	0.071 (2)	−0.0031 (16)	0.0008 (17)	0.0032 (19)
C6	0.058 (2)	0.074 (3)	0.077 (3)	−0.011 (2)	0.002 (2)	0.005 (2)
C7	0.076 (3)	0.065 (3)	0.096 (3)	−0.025 (2)	−0.003 (3)	0.005 (3)
C8	0.070 (3)	0.060 (2)	0.091 (3)	−0.011 (2)	−0.014 (3)	−0.004 (2)
C9	0.061 (2)	0.054 (2)	0.078 (3)	0.0006 (19)	−0.003 (2)	0.000 (2)
C10	0.0430 (19)	0.046 (2)	0.073 (3)	0.0032 (17)	0.0025 (18)	0.0047 (19)
C11	0.115 (4)	0.097 (3)	0.080 (3)	−0.018 (3)	−0.006 (3)	−0.010 (3)

O1—C4	1.235 (3)	C3—H3A	0.9800
N1—C4	1.318 (4)	C4—C5	1.503 (4)
N1—C3	1.457 (4)	C5—C6	1.382 (4)
N1—H1A	0.8600	C5—C10	1.383 (5)
C1—C3	1.488 (6)	C6—C7	1.375 (5)
C1—H1B	0.9600	C6—H6A	0.9300
C1—H1C	0.9600	C7—C8	1.357 (5)
C1—H1D	0.9600	C7—H7A	0.9300
O2—N2	1.203 (3)	C8—C9	1.391 (5)
N2—O3	1.218 (3)	C8—H8A	0.9300
N2—C10	1.475 (4)	C9—C10	1.391 (5)
C2—C3	1.491 (5)	C9—C11	1.499 (5)
C2—H2A	0.9600	C11—H11A	0.9600
C2—H2B	0.9600	C11—H11B	0.9600
C2—H2C	0.9600	C11—H11C	0.9600
C4—N1—C3	123.4 (3)	N1—C4—C5	116.6 (3)
C4—N1—H1A	118.3	C6—C5—C10	116.9 (3)
C3—N1—H1A	118.3	C6—C5—C4	122.0 (3)
C3—C1—H1B	109.5	C10—C5—C4	120.9 (3)
C3—C1—H1C	109.5	C7—C6—C5	120.9 (4)
H1B—C1—H1C	109.5	C7—C6—H6A	119.5
C3—C1—H1D	109.5	C5—C6—H6A	119.5
H1B—C1—H1D	109.5	C8—C7—C6	120.2 (4)
H1C—C1—H1D	109.5	C8—C7—H7A	119.9
O2—N2—O3	124.3 (3)	C6—C7—H7A	119.9
O2—N2—C10	117.5 (3)	C7—C8—C9	122.2 (4)
O3—N2—C10	118.2 (3)	C7—C8—H8A	118.9
C3—C2—H2A	109.5	C9—C8—H8A	118.9
C3—C2—H2B	109.5	C10—C9—C8	115.6 (4)
H2A—C2—H2B	109.5	C10—C9—C11	123.7 (4)
C3—C2—H2C	109.5	C8—C9—C11	120.7 (4)
H2A—C2—H2C	109.5	C5—C10—C9	124.1 (3)
H2B—C2—H2C	109.5	C5—C10—N2	118.0 (3)
N1—C3—C1	111.4 (3)	C9—C10—N2	117.8 (3)
N1—C3—C2	110.1 (3)	C9—C11—H11A	109.5
C1—C3—C2	111.3 (4)	C9—C11—H11B	109.5
N1—C3—H3A	108.0	H11A—C11—H11B	109.5
C1—C3—H3A	108.0	C9—C11—H11C	109.5
C2—C3—H3A	108.0	H11A—C11—H11C	109.5
O1—C4—N1	124.1 (3)	H11B—C11—H11C	109.5
O1—C4—C5	119.3 (3)
C4—N1—C3—C1	−95.0 (4)	C7—C8—C9—C11	−178.9 (4)
C4—N1—C3—C2	141.1 (4)	C6—C5—C10—C9	1.1 (5)
C3—N1—C4—O1	−3.0 (6)	C4—C5—C10—C9	176.8 (3)
C3—N1—C4—C5	175.6 (3)	C6—C5—C10—N2	179.1 (3)
O1—C4—C5—C6	132.9 (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—C5	178.0 (4)
N1—C4—C5—C10	138.7 (3)	C8—C9—C10—N2	−178.8 (3)
C10—C5—C6—C7	−0.6 (5)	C11—C9—C10—N2	0.0 (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—C5	118.6 (4)
C6—C7—C8—C9	0.5 (6)	O2—N2—C10—C9	115.6 (4)
C7—C8—C9—C10	0.0 (6)	O3—N2—C10—C9	−63.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.86	2.00	2.855 (3)	173
C11—H11A···O3	0.96	2.37	3.021 (5)	124

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.86	2.00	2.855 (3)	173
C11—H11A⋯O3	0.96	2.37	3.021 (5)	124

Symmetry code: (i) .