Methyl 3-amino-4-butanamido-5-methyl-benzoate.

The title compound, C(13)H(18)N(2)O(3), is an inter-mediate in the synthesis of compounds with medicinial applications. The crystal structure is stabilized by inter-molecular N-H⋯O, C-H⋯N and C-H⋯O hydrogen bonds.

Related literature

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

Experimental

Crystal data

C13H18N2O3

M = 250.29

Monoclinic,

a = 10.547 (2) Å

b = 16.258 (3) Å

c = 8.430 (2) Å

β = 111.69 (3)°

V = 1343.2 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 (2) K

0.40 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.965, T max = 0.991

2579 measured reflections

2404 independent reflections

1511 reflections with I > 2σ(I)

R int = 0.028

3 standard reflections every 200 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.074

wR(F 2) = 0.174

S = 1.02

2404 reflections

158 parameters

H-atom parameters constrained

Δρmax = 0.50 e Å−3

Δρmin = −0.40 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: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808013408/im2061sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808013408/im2061Isup2.hkl

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

C13H18N2O3	F000 = 536
Mr = 250.29	Dx = 1.238 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 10.547 (2) Å	θ = 10–13º
b = 16.258 (3) Å	µ = 0.09 mm−1
c = 8.430 (2) Å	T = 293 (2) K
β = 111.69 (3)º	Block, colourless
V = 1343.2 (5) Å3	0.40 × 0.20 × 0.10 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	Rint = 0.028
Radiation source: fine-focus sealed tube	θmax = 25.2º
Monochromator: graphite	θmin = 2.1º
T = 293(2) K	h = −12→11
ω/2θ scans	k = 0→19
Absorption correction: ψ scan(North et al., 1968)	l = 0→10
Tmin = 0.965, Tmax = 0.991	3 standard reflections
2579 measured reflections	every 200 reflections
2404 independent reflections	intensity decay: none
1511 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)] = 0.075	H-atom parameters constrained
wR(F2) = 0.174	w = 1/[σ2(Fo2) + (0.05P)2 + 1.5P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.002
2404 reflections	Δρmax = 0.50 e Å−3
158 parameters	Δρmin = −0.40 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	0.7939 (3)	0.28652 (17)	0.4910 (3)	0.0609 (8)
H1A	0.7889	0.2893	0.3870	0.073*
O1	0.9151 (2)	0.31431 (18)	0.7622 (3)	0.0722 (8)
C1	1.2201 (4)	0.4441 (3)	0.6344 (6)	0.1018 (16)
H1B	1.2826	0.4734	0.7305	0.153*
H1C	1.1791	0.4818	0.5418	0.153*
H1D	1.2685	0.4023	0.5994	0.153*
O2	0.3477 (2)	0.05447 (17)	0.6104 (4)	0.0760 (8)
N2	0.7806 (3)	0.11598 (19)	0.5029 (4)	0.0669 (8)
H2A	0.7778	0.0632	0.5085	0.080*
H2B	0.8469	0.1395	0.4845	0.080*
C2	1.1113 (4)	0.4052 (3)	0.6834 (5)	0.084
H2C	1.1555	0.3715	0.7836	0.100*
H2D	1.0630	0.4487	0.7163	0.100*
O3	0.2717 (2)	0.17791 (16)	0.6464 (3)	0.0690 (7)
C3	1.0098 (4)	0.3540 (2)	0.5540 (4)	0.0620 (9)
H3A	1.0570	0.3098	0.5213	0.074*
H3B	0.9645	0.3872	0.4533	0.074*
C4	0.9036 (3)	0.31730 (19)	0.6119 (4)	0.0483 (8)
C5	0.6835 (3)	0.2489 (2)	0.5237 (4)	0.0522 (8)
C6	0.5855 (3)	0.2967 (2)	0.5521 (4)	0.0543 (8)
C7	0.4796 (3)	0.2576 (2)	0.5839 (4)	0.0537 (8)
H7A	0.4141	0.2888	0.6061	0.064*
C8	0.4715 (3)	0.1723 (2)	0.5825 (3)	0.0479 (8)
C9	0.5702 (3)	0.1258 (2)	0.5536 (4)	0.0511 (8)
H9A	0.5644	0.0687	0.5541	0.061*
C10	0.6789 (3)	0.1628 (2)	0.5235 (4)	0.0515 (8)
C11	0.5897 (4)	0.3891 (2)	0.5480 (5)	0.0723 (11)
H11A	0.6766	0.4066	0.5478	0.108*
H11B	0.5768	0.4109	0.6468	0.108*
H11C	0.5185	0.4088	0.4467	0.108*
C12	0.3588 (3)	0.1281 (2)	0.6125 (4)	0.0540 (8)
C13	0.1601 (4)	0.1399 (3)	0.6781 (5)	0.0876 (13)
H13A	0.1050	0.1817	0.7013	0.131*
H13B	0.1953	0.1038	0.7746	0.131*
H13C	0.1056	0.1090	0.5794	0.131*

	U11	U22	U33	U12	U13	U23
N1	0.0727 (19)	0.078 (2)	0.0357 (14)	−0.0270 (16)	0.0244 (14)	−0.0037 (14)
O1	0.0547 (14)	0.120 (2)	0.0446 (13)	−0.0178 (14)	0.0212 (11)	−0.0041 (13)
C1	0.088 (3)	0.127 (4)	0.099 (3)	−0.049 (3)	0.044 (3)	−0.021 (3)
O2	0.0629 (16)	0.0679 (18)	0.106 (2)	−0.0081 (13)	0.0415 (15)	0.0052 (15)
N2	0.0536 (17)	0.074 (2)	0.082 (2)	−0.0098 (15)	0.0355 (16)	−0.0048 (17)
C2	0.084	0.084	0.084	0.000	0.031	0.000
O3	0.0547 (14)	0.0824 (18)	0.0749 (17)	−0.0004 (13)	0.0296 (13)	0.0048 (13)
C3	0.063 (2)	0.072 (2)	0.059 (2)	−0.0144 (19)	0.0328 (18)	−0.0081 (18)
C4	0.0546 (19)	0.0550 (19)	0.0413 (17)	0.0012 (16)	0.0248 (15)	−0.0036 (15)
C5	0.056 (2)	0.069 (2)	0.0284 (15)	−0.0165 (17)	0.0127 (14)	−0.0038 (15)
C6	0.060 (2)	0.060 (2)	0.0363 (16)	−0.0098 (17)	0.0099 (15)	0.0002 (15)
C7	0.0500 (19)	0.061 (2)	0.0455 (18)	−0.0014 (16)	0.0124 (15)	0.0019 (16)
C8	0.0437 (17)	0.061 (2)	0.0325 (15)	−0.0059 (15)	0.0059 (13)	0.0010 (14)
C9	0.0435 (18)	0.0570 (19)	0.0483 (18)	−0.0042 (15)	0.0118 (15)	0.0038 (15)
C10	0.0456 (18)	0.066 (2)	0.0382 (16)	−0.0081 (16)	0.0102 (14)	−0.0020 (15)
C11	0.082 (3)	0.067 (2)	0.066 (2)	−0.010 (2)	0.025 (2)	0.0051 (19)
C12	0.0473 (19)	0.069 (2)	0.0418 (17)	0.0004 (18)	0.0121 (15)	0.0052 (17)
C13	0.063 (2)	0.123 (4)	0.093 (3)	0.004 (2)	0.048 (2)	0.020 (3)

N1—C4	1.325 (4)	C3—H3A	0.9700
N1—C5	1.430 (4)	C3—H3B	0.9700
N1—H1A	0.8600	C5—C6	1.384 (5)
O1—C4	1.229 (3)	C5—C10	1.400 (5)
C1—C2	1.496 (5)	C6—C7	1.394 (4)
C1—H1B	0.9600	C6—C11	1.503 (5)
C1—H1C	0.9600	C7—C8	1.391 (4)
C1—H1D	0.9600	C7—H7A	0.9300
O2—C12	1.202 (4)	C8—C9	1.379 (4)
N2—C10	1.378 (4)	C8—C12	1.488 (4)
N2—H2A	0.8600	C9—C10	1.399 (4)
N2—H2B	0.8600	C9—H9A	0.9300
C2—C3	1.472 (5)	C11—H11A	0.9600
C2—H2C	0.9700	C11—H11B	0.9600
C2—H2D	0.9700	C11—H11C	0.9600
O3—C12	1.333 (4)	C13—H13A	0.9600
O3—C13	1.439 (4)	C13—H13B	0.9600
C3—C4	1.500 (4)	C13—H13C	0.9600
C4—N1—C5	123.7 (2)	C5—C6—C7	118.6 (3)
C4—N1—H1A	118.1	C5—C6—C11	121.8 (3)
C5—N1—H1A	118.1	C7—C6—C11	119.5 (3)
C2—C1—H1B	109.5	C8—C7—C6	120.3 (3)
C2—C1—H1C	109.5	C8—C7—H7A	119.8
H1B—C1—H1C	109.5	C6—C7—H7A	119.8
C2—C1—H1D	109.5	C9—C8—C7	120.0 (3)
H1B—C1—H1D	109.5	C9—C8—C12	117.9 (3)
H1C—C1—H1D	109.5	C7—C8—C12	122.1 (3)
C10—N2—H2A	120.0	C8—C9—C10	121.3 (3)
C10—N2—H2B	120.0	C8—C9—H9A	119.4
H2A—N2—H2B	120.0	C10—C9—H9A	119.4
C3—C2—C1	117.2 (3)	N2—C10—C9	120.9 (3)
C3—C2—H2C	108.0	N2—C10—C5	121.7 (3)
C1—C2—H2C	108.0	C9—C10—C5	117.4 (3)
C3—C2—H2D	108.0	C6—C11—H11A	109.5
C1—C2—H2D	108.0	C6—C11—H11B	109.5
H2C—C2—H2D	107.2	H11A—C11—H11B	109.5
C12—O3—C13	117.1 (3)	C6—C11—H11C	109.5
C2—C3—C4	114.2 (3)	H11A—C11—H11C	109.5
C2—C3—H3A	108.7	H11B—C11—H11C	109.5
C4—C3—H3A	108.7	O2—C12—O3	122.5 (3)
C2—C3—H3B	108.7	O2—C12—C8	123.9 (3)
C4—C3—H3B	108.7	O3—C12—C8	113.6 (3)
H3A—C3—H3B	107.6	O3—C13—H13A	109.5
O1—C4—N1	120.2 (3)	O3—C13—H13B	109.5
O1—C4—C3	123.4 (3)	H13A—C13—H13B	109.5
N1—C4—C3	116.4 (3)	O3—C13—H13C	109.5
C6—C5—C10	122.3 (3)	H13A—C13—H13C	109.5
C6—C5—N1	120.4 (3)	H13B—C13—H13C	109.5
C10—C5—N1	117.2 (3)
C1—C2—C3—C4	−179.7 (4)	C7—C8—C9—C10	−0.7 (4)
C5—N1—C4—O1	0.2 (5)	C12—C8—C9—C10	179.7 (3)
C5—N1—C4—C3	179.6 (3)	C8—C9—C10—N2	176.8 (3)
C2—C3—C4—O1	−15.3 (5)	C8—C9—C10—C5	0.0 (4)
C2—C3—C4—N1	165.4 (3)	C6—C5—C10—N2	−176.9 (3)
C4—N1—C5—C6	79.5 (4)	N1—C5—C10—N2	3.8 (4)
C4—N1—C5—C10	−101.3 (4)	C6—C5—C10—C9	−0.1 (5)
C10—C5—C6—C7	0.9 (5)	N1—C5—C10—C9	−179.3 (2)
N1—C5—C6—C7	−179.9 (3)	C13—O3—C12—O2	−1.1 (5)
C10—C5—C6—C11	−178.5 (3)	C13—O3—C12—C8	−179.6 (3)
N1—C5—C6—C11	0.7 (5)	C9—C8—C12—O2	−1.2 (5)
C5—C6—C7—C8	−1.6 (5)	C7—C8—C12—O2	179.2 (3)
C11—C6—C7—C8	177.8 (3)	C9—C8—C12—O3	177.3 (3)
C6—C7—C8—C9	1.6 (5)	C7—C8—C12—O3	−2.4 (4)
C6—C7—C8—C12	−178.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.86	2.60	3.141 (4)	122
N2—H2A···O2ii	0.86	2.33	3.077 (4)	145
N2—H2B···N1	0.86	2.46	2.780 (4)	103
N2—H2B···O1i	0.86	2.36	3.089 (4)	142
C11—H11A···N1	0.96	2.45	2.901 (5)	108

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.86	2.60	3.141 (4)	122
N2—H2A⋯O2ii	0.86	2.33	3.077 (4)	145
N2—H2B⋯N1	0.86	2.46	2.780 (4)	103
N2—H2B⋯O1i	0.86	2.36	3.089 (4)	142
C11—H11A⋯N1	0.96	2.45	2.901 (5)	108

Symmetry codes: (i) ; (ii) .