Methyl 4-(butyrylamino)-5-methyl-2-nitro-benzoate.

The title compound, C(13)H(16)N(2)O(5), is useful as an inter-mediate in the field of agrochemicals. Intra-molecular C-H⋯O hydrogen bonds result in the formation of one six- and one five-membered nearly planar ring; the six-membered ring is also nearly coplanar with the adjacent benzene ring. In the crystal structure, inter-molecular C-H⋯O hydrogen bonds link the mol-ecules.

Related literature

For related literature, see: Ries et al. (1993 ▶); Engeli et al. (2000 ▶); Kintscher et al. (2004 ▶); Goossens et al. (2003 ▶); Boustany et al. (2004 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C13H16N2O5

M = 280.28

Triclinic,

a = 7.6370 (15) Å

b = 8.7880 (18) Å

c = 11.329 (2) Å

α = 81.06 (3)°

β = 78.48 (3)°

γ = 68.39 (3)°

V = 689.9 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 294 (2) 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 = 0.959, T max = 0.980

2919 measured reflections

2704 independent reflections

1650 reflections with I > 2σ(I)

R int = 0.032

3 standard reflections frequency: 120 min intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.161

S = 1.01

2704 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.18 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808005576/hk2408sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808005576/hk2408Isup2.hkl

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

C13H16N2O5	Z = 2
Mr = 280.28	F000 = 296
Triclinic, P1	Dx = 1.349 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 7.6370 (15) Å	Cell parameters from 25 reflections
b = 8.7880 (18) Å	θ = 9–14º
c = 11.329 (2) Å	µ = 0.11 mm−1
α = 81.06 (3)º	T = 294 (2) K
β = 78.48 (3)º	Block, colorless
γ = 68.39 (3)º	0.30 × 0.20 × 0.10 mm
V = 689.9 (3) Å3

Enraf–Nonius CAD-4 diffractometer	Rint = 0.032
Radiation source: fine-focus sealed tube	θmax = 26.0º
Monochromator: graphite	θmin = 1.8º
T = 294(2) K	h = −9→9
ω/2θ scans	k = −10→10
Absorption correction: ψ scan(North et al., 1968)	l = 0→13
Tmin = 0.959, Tmax = 0.980	3 standard reflections
2919 measured reflections	every 120 min
2704 independent reflections	intensity decay: none
1650 reflections with I > 2σ(I)

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)] = 0.056	H-atom parameters constrained
wR(F2) = 0.161	w = 1/[σ2(Fo2) + (0.06P)2 + 0.4P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
2704 reflections	Δρmax = 0.20 e Å−3
181 parameters	Δρmin = −0.18 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq
N1	0.2769 (4)	−0.1219 (3)	−0.0125 (2)	0.0492 (6)
H1A	0.3013	−0.2242	0.0119	0.059*
O1	0.2083 (4)	0.0590 (3)	−0.1748 (2)	0.0845 (9)
C1	0.2766 (5)	−0.3253 (4)	−0.3938 (3)	0.0681 (10)
H1B	0.2607	−0.2909	−0.4769	0.102*
H1C	0.1823	−0.3727	−0.3551	0.102*
H1D	0.4016	−0.4056	−0.3901	0.102*
N2	0.1750 (4)	0.4161 (3)	0.1056 (2)	0.0454 (6)
O2	0.0124 (3)	0.5069 (2)	0.1365 (2)	0.0693 (7)
C2	0.2531 (5)	−0.1773 (4)	−0.3296 (3)	0.0520 (8)
H2A	0.3459	−0.1278	−0.3706	0.062*
H2B	0.1270	−0.0962	−0.3341	0.062*
O3	0.3005 (3)	0.4618 (3)	0.0453 (2)	0.0634 (7)
C3	0.2792 (4)	−0.2244 (3)	−0.1980 (2)	0.0454 (7)
H3A	0.1893	−0.2776	−0.1582	0.054*
H3B	0.4066	−0.3034	−0.1941	0.054*
O4	0.2265 (3)	0.1922 (2)	0.46212 (17)	0.0595 (6)
C4	0.2510 (4)	−0.0805 (3)	−0.1302 (2)	0.0445 (7)
O5	0.2355 (3)	0.4105 (2)	0.33631 (17)	0.0585 (6)
C5	0.2695 (4)	−0.0219 (3)	0.0744 (2)	0.0397 (6)
C6	0.2311 (4)	0.1466 (3)	0.0483 (2)	0.0383 (6)
H6A	0.2122	0.1962	−0.0291	0.046*
C7	0.2217 (4)	0.2382 (3)	0.1391 (2)	0.0356 (6)
C8	0.2483 (4)	0.1712 (3)	0.2565 (2)	0.0394 (6)
C9	0.2896 (4)	0.0022 (3)	0.2777 (2)	0.0461 (7)
H9A	0.3106	−0.0474	0.3548	0.055*
C10	0.3010 (4)	−0.0948 (3)	0.1907 (2)	0.0456 (7)
C11	0.3466 (7)	−0.2777 (4)	0.2205 (3)	0.0822 (13)
H11A	0.3653	−0.3065	0.3035	0.123*
H11B	0.4607	−0.3358	0.1691	0.123*
H11C	0.2428	−0.3069	0.2079	0.123*
C12	0.2353 (4)	0.2736 (3)	0.3534 (2)	0.0402 (6)
C13	0.2136 (6)	0.2797 (4)	0.5634 (3)	0.0723 (11)
H13A	0.2095	0.2093	0.6370	0.108*
H13B	0.0999	0.3754	0.5674	0.108*
H13C	0.3230	0.3125	0.5531	0.108*

	U11	U22	U33	U12	U13	U23
N1	0.0804 (19)	0.0346 (12)	0.0354 (12)	−0.0212 (12)	−0.0131 (12)	−0.0035 (9)
O1	0.165 (3)	0.0436 (13)	0.0494 (13)	−0.0360 (15)	−0.0326 (15)	0.0018 (10)
C1	0.090 (3)	0.072 (2)	0.0495 (19)	−0.032 (2)	−0.0078 (18)	−0.0197 (16)
N2	0.0652 (17)	0.0380 (13)	0.0380 (13)	−0.0210 (13)	−0.0154 (12)	−0.0009 (10)
O2	0.0695 (16)	0.0383 (12)	0.0819 (17)	0.0019 (11)	−0.0134 (13)	−0.0029 (11)
C2	0.059 (2)	0.0473 (16)	0.0487 (17)	−0.0144 (14)	−0.0101 (15)	−0.0114 (13)
O3	0.0922 (18)	0.0483 (12)	0.0568 (13)	−0.0405 (12)	−0.0019 (12)	0.0022 (10)
C3	0.0543 (18)	0.0422 (15)	0.0443 (16)	−0.0216 (13)	−0.0042 (13)	−0.0099 (12)
O4	0.1073 (18)	0.0430 (11)	0.0345 (11)	−0.0323 (11)	−0.0149 (11)	−0.0013 (9)
C4	0.0537 (18)	0.0375 (15)	0.0423 (16)	−0.0169 (13)	−0.0060 (13)	−0.0029 (12)
O5	0.1011 (18)	0.0393 (11)	0.0447 (12)	−0.0343 (11)	−0.0136 (11)	−0.0036 (9)
C5	0.0521 (17)	0.0328 (13)	0.0365 (14)	−0.0161 (12)	−0.0063 (12)	−0.0072 (11)
C6	0.0496 (17)	0.0333 (13)	0.0312 (13)	−0.0133 (12)	−0.0063 (12)	−0.0035 (10)
C7	0.0435 (16)	0.0272 (12)	0.0377 (14)	−0.0140 (11)	−0.0081 (12)	−0.0007 (10)
C8	0.0469 (17)	0.0336 (13)	0.0402 (15)	−0.0168 (12)	−0.0065 (12)	−0.0036 (11)
C9	0.071 (2)	0.0356 (14)	0.0319 (14)	−0.0193 (14)	−0.0096 (13)	0.0002 (11)
C10	0.070 (2)	0.0306 (13)	0.0362 (14)	−0.0193 (13)	−0.0060 (13)	−0.0003 (11)
C11	0.164 (4)	0.0358 (16)	0.0499 (19)	−0.035 (2)	−0.026 (2)	0.0017 (14)
C12	0.0459 (17)	0.0356 (14)	0.0384 (15)	−0.0138 (12)	−0.0063 (12)	−0.0028 (11)
C13	0.129 (3)	0.0519 (19)	0.0386 (18)	−0.032 (2)	−0.0169 (19)	−0.0070 (14)

N1—C4	1.361 (3)	O4—C13	1.446 (3)
N1—C5	1.398 (3)	O5—C12	1.190 (3)
N1—H1A	0.8600	C5—C6	1.394 (3)
O1—C4	1.202 (3)	C5—C10	1.399 (4)
C1—C2	1.524 (4)	C6—C7	1.377 (3)
C1—H1B	0.9600	C6—H6A	0.9300
C1—H1C	0.9600	C7—C8	1.391 (3)
C1—H1D	0.9600	C8—C9	1.391 (4)
N2—O3	1.218 (3)	C8—C12	1.490 (4)
N2—O2	1.218 (3)	C9—C10	1.370 (4)
N2—C7	1.474 (3)	C9—H9A	0.9300
C2—C3	1.516 (4)	C10—C11	1.512 (4)
C2—H2A	0.9700	C11—H11A	0.9600
C2—H2B	0.9700	C11—H11B	0.9600
C3—C4	1.507 (4)	C11—H11C	0.9600
C3—H3A	0.9700	C13—H13A	0.9600
C3—H3B	0.9700	C13—H13B	0.9600
O4—C12	1.327 (3)	C13—H13C	0.9600
C4—N1—C5	129.3 (2)	C7—C6—C5	118.9 (2)
C4—N1—H1A	115.4	C7—C6—H6A	120.6
C5—N1—H1A	115.4	C5—C6—H6A	120.6
C2—C1—H1B	109.5	C6—C7—C8	123.3 (2)
C2—C1—H1C	109.5	C6—C7—N2	115.7 (2)
H1B—C1—H1C	109.5	C8—C7—N2	121.0 (2)
C2—C1—H1D	109.5	C7—C8—C9	115.8 (2)
H1B—C1—H1D	109.5	C7—C8—C12	122.1 (2)
H1C—C1—H1D	109.5	C9—C8—C12	122.1 (2)
O3—N2—O2	124.3 (2)	C10—C9—C8	123.4 (3)
O3—N2—C7	117.5 (2)	C10—C9—H9A	118.3
O2—N2—C7	118.1 (2)	C8—C9—H9A	118.3
C3—C2—C1	112.0 (3)	C9—C10—C5	119.0 (2)
C3—C2—H2A	109.2	C9—C10—C11	120.3 (2)
C1—C2—H2A	109.2	C5—C10—C11	120.7 (2)
C3—C2—H2B	109.2	C10—C11—H11A	109.5
C1—C2—H2B	109.2	C10—C11—H11B	109.5
H2A—C2—H2B	107.9	H11A—C11—H11B	109.5
C4—C3—C2	113.6 (2)	C10—C11—H11C	109.5
C4—C3—H3A	108.8	H11A—C11—H11C	109.5
C2—C3—H3A	108.8	H11B—C11—H11C	109.5
C4—C3—H3B	108.8	O5—C12—O4	123.6 (2)
C2—C3—H3B	108.8	O5—C12—C8	124.7 (2)
H3A—C3—H3B	107.7	O4—C12—C8	111.7 (2)
C12—O4—C13	116.5 (2)	O4—C13—H13A	109.5
O1—C4—N1	122.4 (3)	O4—C13—H13B	109.5
O1—C4—C3	123.6 (3)	H13A—C13—H13B	109.5
N1—C4—C3	114.0 (2)	O4—C13—H13C	109.5
C6—C5—N1	122.0 (2)	H13A—C13—H13C	109.5
C6—C5—C10	119.7 (2)	H13B—C13—H13C	109.5
N1—C5—C10	118.3 (2)
C1—C2—C3—C4	−178.2 (3)	C6—C7—C8—C12	−179.3 (3)
C5—N1—C4—O1	−3.1 (5)	N2—C7—C8—C12	−1.3 (4)
C5—N1—C4—C3	177.3 (3)	C7—C8—C9—C10	−1.1 (4)
C2—C3—C4—O1	1.4 (4)	C12—C8—C9—C10	179.5 (3)
C2—C3—C4—N1	−179.1 (3)	C8—C9—C10—C5	−0.1 (5)
C4—N1—C5—C6	0.1 (5)	C8—C9—C10—C11	180.0 (3)
C4—N1—C5—C10	179.8 (3)	C6—C5—C10—C9	1.3 (4)
N1—C5—C6—C7	178.5 (3)	N1—C5—C10—C9	−178.4 (3)
C10—C5—C6—C7	−1.2 (4)	C6—C5—C10—C11	−178.8 (3)
C5—C6—C7—C8	−0.1 (4)	N1—C5—C10—C11	1.5 (4)
C5—C6—C7—N2	−178.3 (2)	C13—O4—C12—O5	1.0 (4)
O3—N2—C7—C6	−75.9 (3)	C13—O4—C12—C8	179.9 (3)
O2—N2—C7—C6	101.7 (3)	C7—C8—C12—O5	−13.9 (4)
O3—N2—C7—C8	105.9 (3)	C9—C8—C12—O5	165.5 (3)
O2—N2—C7—C8	−76.5 (3)	C7—C8—C12—O4	167.1 (3)
C6—C7—C8—C9	1.2 (4)	C9—C8—C12—O4	−13.5 (4)
N2—C7—C8—C9	179.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···O1	0.93	2.20	2.809 (3)	122
C9—H9A···O4	0.93	2.41	2.734 (3)	100
C13—H13A···O1i	0.96	2.33	3.284 (4)	174

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6A⋯O1	0.93	2.20	2.809 (3)	122
C9—H9A⋯O4	0.93	2.41	2.734 (3)	100
C13—H13A⋯O1i	0.96	2.33	3.284 (4)	174

Symmetry code: (i) .