Methyl 6-amino-6-oxohexa-noate.

The title compound, C(7)H(13)NO(3), adopts an approximately planar conformation. The torsion angles in the aliphatic chain between the carbonyl group C atoms range from 172.97 (14) to 179.38 (14)° and the r.m.s. deviation of all non-H atoms is 0.059 Å. The crystal packing is dominated by two strong N-H⋯O hydrogen bonds involving the amide groups and forming R(2) (2)(8) rings and C(4) chains. Overall, a two-dimensional network parallel to (100) is formed. A weak inter-molecular C-H⋯O inter-action is also present.

Related literature

For the synthesis of the title compound, see: Kulikova et al. (1960 ▶); Nishitani et al. (1982 ▶); Micovic et al. (1988 ▶). For information on the solid-state characteristics of different polymorphs of adipic acid, see: Fun & Chantrapromma (2009 ▶); Ranganathan et al. (2003 ▶); Srinivasa Gopalan et al. (1999 ▶, 2000 ▶); Pfefer & Boistelle (2000 ▶); Housty & Hospital (1965 ▶); Arevalo & Canut (1961 ▶); Hirokawa (1950 ▶); Morrison & Robertson (1949 ▶); MacGillavry (1941 ▶). For details on co-crystals of the title compound, see: Goswami et al. (2010 ▶); Delori et al. (2008 ▶); Bucar et al. (2007 ▶); Childs & Hardcastle (2007 ▶); Duan et al. (2005 ▶); Li et al. (2001 ▶); Urbanczyk-Lipkowska & Gluzinski (1996 ▶). For other reports of adipic acid derivatives, see: Li & Goddard (2002 ▶); Seaton & Tremayne (2002 ▶); Hospital & Housty (1966 ▶). For uses of the title compound in heterocycle synthesis, see: Jungheim et al. (2005 ▶); Fukumoto et al. (2007 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For details of the H-atom treatment, see: Cooper et al. (2010 ▶).

Experimental

Crystal data

C7H13NO3

M = 159.19

Monoclinic,

a = 12.896 (3) Å

b = 7.2143 (8) Å

c = 9.6324 (12) Å

β = 106.474 (17)°

V = 859.4 (2) Å3

Z = 4

Cu Kα radiation

μ = 0.80 mm−1

T = 150 K

0.18 × 0.12 × 0.02 mm

Data collection

Agilent SuperNova Dual (Cu at zero) diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.48, T max = 0.98

7240 measured reflections

1771 independent reflections

1426 reflections with I > 2σ(I)

R int = 0.035

Standard reflections: 0

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.128

S = 1.00

1770 reflections

100 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.24 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ▶); molecular graphics: CAMERON (Watkin et al., 1996 ▶); software used to prepare material for publication: CRYSTALS and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812003303/lh5383sup1.cif

Supplementary material file. DOI: 10.1107/S1600536812003303/lh5383Isup2.cdx

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812003303/lh5383Isup3.hkl

Supplementary material file. DOI: 10.1107/S1600536812003303/lh5383Isup4.cml

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

C7H13NO3	F(000) = 344
Mr = 159.19	Dx = 1.230 Mg m−3
Monoclinic, P21/c	Melting point: not measured K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54184 Å
a = 12.896 (3) Å	Cell parameters from 2081 reflections
b = 7.2143 (8) Å	θ = 4–76°
c = 9.6324 (12) Å	µ = 0.80 mm−1
β = 106.474 (17)°	T = 150 K
V = 859.4 (2) Å3	Lath, clear_pale_colourless
Z = 4	0.18 × 0.12 × 0.02 mm

Agilent SuperNova Dual (Cu at zero) diffractometer with an Atlas detector	1426 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
ω scans	θmax = 76.0°, θmin = 3.6°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	h = −16→15
Tmin = 0.48, Tmax = 0.98	k = −9→7
7240 measured reflections	l = −12→11
1771 independent reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044	H-atom parameters constrained
wR(F2) = 0.128	Method = Modified Sheldrick w = 1/[σ2(F2) + ( 0.07P)2 + 0.22P], where P = (max(Fo2,0) + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.001
1770 reflections	Δρmax = 0.24 e Å−3
100 parameters	Δρmin = −0.24 e Å−3
0 restraints

Experimental. Agilent Technologies (2010). CrysAlisPro. Version 1.171.35.4 (release 09-12-2010 CrysAlis171 .NET) (compiled Dec 9 2010,10:47:41) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

	x	y	z	Uiso*/Ueq
O1	0.07129 (11)	1.29877 (15)	0.44865 (11)	0.0413
C2	0.09105 (12)	1.2640 (2)	0.58008 (14)	0.0323
N3	0.05751 (12)	1.37331 (17)	0.66941 (12)	0.0372
H31	0.0242	1.4758	0.6389	0.0445*
H32	0.0717	1.3426	0.7589	0.0449*
C4	0.15519 (14)	1.0967 (2)	0.64774 (15)	0.0380
C5	0.18119 (13)	0.9615 (2)	0.54141 (15)	0.0339
C6	0.24703 (14)	0.7987 (2)	0.62007 (15)	0.0373
C7	0.27433 (15)	0.6613 (2)	0.51664 (17)	0.0417
C8	0.34505 (14)	0.5046 (2)	0.59123 (17)	0.0411
O9	0.36947 (12)	0.39151 (19)	0.49492 (14)	0.0571
C10	0.43990 (18)	0.2384 (3)	0.5546 (2)	0.0604
H101	0.4474	0.1631	0.4773	0.0899*
H103	0.5097	0.2837	0.6123	0.0882*
H102	0.4069	0.1646	0.6164	0.0903*
O11	0.37696 (14)	0.48159 (19)	0.71881 (14)	0.0605
H71	0.3122	0.7249	0.4570	0.0507*
H72	0.2080	0.6062	0.4549	0.0501*
H62	0.3138	0.8436	0.6854	0.0443*
H61	0.2066	0.7354	0.6763	0.0458*
H52	0.2233	1.0258	0.4878	0.0396*
H51	0.1133	0.9163	0.4743	0.0412*
H41	0.2227	1.1408	0.7133	0.0470*
H42	0.1152	1.0285	0.7024	0.0471*

	U11	U22	U33	U12	U13	U23
O1	0.0675 (8)	0.0363 (6)	0.0230 (5)	0.0117 (5)	0.0176 (5)	0.0041 (4)
C2	0.0438 (8)	0.0298 (7)	0.0251 (6)	−0.0007 (6)	0.0126 (6)	0.0004 (5)
N3	0.0586 (8)	0.0333 (6)	0.0223 (5)	0.0073 (6)	0.0154 (5)	0.0023 (4)
C4	0.0549 (9)	0.0355 (8)	0.0247 (6)	0.0069 (7)	0.0133 (6)	0.0033 (5)
C5	0.0441 (8)	0.0312 (7)	0.0269 (6)	0.0011 (6)	0.0109 (5)	−0.0001 (5)
C6	0.0521 (9)	0.0317 (7)	0.0281 (7)	0.0030 (6)	0.0112 (6)	0.0006 (5)
C7	0.0532 (9)	0.0378 (8)	0.0327 (7)	0.0066 (7)	0.0100 (7)	−0.0031 (6)
C8	0.0461 (9)	0.0330 (8)	0.0408 (8)	−0.0015 (6)	0.0070 (7)	−0.0036 (6)
O9	0.0645 (8)	0.0499 (7)	0.0489 (7)	0.0206 (6)	0.0031 (6)	−0.0128 (5)
C10	0.0552 (11)	0.0471 (10)	0.0707 (13)	0.0130 (9)	0.0046 (9)	−0.0113 (9)
O11	0.0857 (10)	0.0492 (7)	0.0424 (7)	0.0185 (7)	0.0111 (7)	0.0068 (5)

O1—C2	1.2441 (18)	C6—H62	0.967
C2—N3	1.3269 (19)	C6—H61	0.966
C2—C4	1.503 (2)	C7—C8	1.501 (2)
N3—H31	0.864	C7—H71	0.969
N3—H32	0.858	C7—H72	0.977
C4—C5	1.5193 (19)	C8—O9	1.338 (2)
C4—H41	0.972	C8—O11	1.192 (2)
C4—H42	0.970	O9—C10	1.442 (2)
C5—C6	1.520 (2)	C10—H101	0.949
C5—H52	0.967	C10—H103	0.971
C5—H51	0.984	C10—H102	0.981
C6—C7	1.516 (2)
O1—C2—N3	121.98 (13)	C7—C6—H62	108.5
O1—C2—C4	122.14 (13)	C5—C6—H61	109.3
N3—C2—C4	115.88 (12)	C7—C6—H61	108.8
C2—N3—H31	120.7	H62—C6—H61	108.4
C2—N3—H32	118.8	C6—C7—C8	113.61 (13)
H31—N3—H32	120.4	C6—C7—H71	109.3
C2—C4—C5	115.01 (11)	C8—C7—H71	107.5
C2—C4—H41	107.5	C6—C7—H72	109.9
C5—C4—H41	108.7	C8—C7—H72	107.0
C2—C4—H42	109.3	H71—C7—H72	109.5
C5—C4—H42	107.1	C7—C8—O9	110.96 (14)
H41—C4—H42	109.2	C7—C8—O11	125.70 (15)
C4—C5—C6	111.05 (12)	O9—C8—O11	123.34 (16)
C4—C5—H52	108.5	C8—O9—C10	115.85 (15)
C6—C5—H52	108.5	O9—C10—H101	108.6
C4—C5—H51	109.3	O9—C10—H103	110.4
C6—C5—H51	109.8	H101—C10—H103	110.9
H52—C5—H51	109.7	O9—C10—H102	109.0
C5—C6—C7	112.25 (12)	H101—C10—H102	108.9
C5—C6—H62	109.5	H103—C10—H102	109.1

D—H···A	D—H	H···A	D···A	D—H···A
N3—H31···O1i	0.86	2.07	2.929 (2)	173 (1)
N3—H32···O1ii	0.86	2.09	2.922 (2)	162 (1)
C10—H101···O11iii	0.95	2.61	3.486 (3)	153 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H31⋯O1i	0.86	2.07	2.929 (2)	173 (1)
N3—H32⋯O1ii	0.86	2.09	2.922 (2)	162 (1)
C10—H101⋯O11iii	0.95	2.61	3.486 (3)	153 (1)

Symmetry codes: (i) ; (ii) ; (iii) .