3,3'-[(tert-Butoxy-carbon-yl)aza-nedi-yl]dipropanoic acid.

The title compound, C(11)H(19)NO(6), is an important inter-mediate for the synthesis of cephalosporin derivatives. The N atom is in a planar configuration. In the crystal, mol-ecules are linked into zigzag layers parallel to (100) by O-H⋯O hydrogen bonds.

Related literature

The condensation of the title compound with cephalosporin may improve the pharmacokinetics, see: Sakagami et al. (1990 ▶, 1991 ▶); Uhrich & Frechet (1992 ▶).

Experimental

Crystal data

C11H19NO6

M = 261.27

Orthorhombic,

a = 10.632 (2) Å

b = 14.559 (3) Å

c = 18.257 (4) Å

V = 2826.1 (11) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 292 K

0.60 × 0.50 × 0.44 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: none

2979 measured reflections

2601 independent reflections

1050 reflections with I > 2σ(I)

R int = 0.008

3 standard reflections every 200 reflections intensity decay: 1.3%

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.171

S = 1.09

2601 reflections

175 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.25 e Å−3

Data collection: DIFRAC (Gabe & White, 1993 ▶); cell refinement: DIFRAC; data reduction: NRCVAX (Gabe et al., 1989 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809018911/ci2799sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018911/ci2799Isup2.hkl

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

C11H19NO6	F(000) = 1120
Mr = 261.27	Dx = 1.228 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 20 reflections
a = 10.632 (2) Å	θ = 5.7–6.8°
b = 14.559 (3) Å	µ = 0.10 mm−1
c = 18.257 (4) Å	T = 292 K
V = 2826.1 (11) Å3	Block, colourless
Z = 8	0.60 × 0.50 × 0.44 mm

Enraf–Nonius CAD-4 diffractometer	Rint = 0.008
Radiation source: fine-focus sealed tube	θmax = 25.5°, θmin = 2.2°
graphite	h = −1→12
ω/2–θ scans	k = −3→17
2979 measured reflections	l = −10→22
2601 independent reflections	3 standard reflections every 200 reflections
1050 reflections with I > 2σ(I)	intensity decay: 1.3%

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)] = 0.054	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.171	w = 1/[σ2(Fo2) + (0.0701P)2] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max = 0.001
2601 reflections	Δρmax = 0.22 e Å−3
175 parameters	Δρmin = −0.25 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: 0.0127 (17)

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
O1	0.1690 (2)	0.18631 (13)	0.36711 (10)	0.0709 (7)
O2	0.0153 (3)	0.10681 (16)	0.31021 (11)	0.0841 (8)
O3	0.0720 (3)	−0.04162 (19)	0.08342 (15)	0.0995 (10)
H3O	0.031 (4)	−0.058 (3)	0.037 (3)	0.129 (16)*
O4	0.0484 (3)	0.09467 (16)	0.03663 (14)	0.1078 (11)
O5	0.1228 (3)	0.49187 (18)	0.26626 (13)	0.0833 (8)
H5O	0.066 (5)	0.526 (3)	0.238 (2)	0.137 (18)*
O6	0.1031 (3)	0.39281 (16)	0.17583 (15)	0.1142 (11)
N1	0.1433 (3)	0.20065 (16)	0.24663 (13)	0.0669 (8)
C1	0.2392 (4)	0.1974 (2)	0.48679 (17)	0.0898 (12)
H1A	0.3223	0.1849	0.4687	0.135*
H1B	0.2328	0.1772	0.5367	0.135*
H1C	0.2233	0.2622	0.4843	0.135*
C2	0.1697 (4)	0.0451 (2)	0.4391 (2)	0.0981 (14)
H2A	0.1055	0.0146	0.4112	0.147*
H2B	0.1700	0.0217	0.4882	0.147*
H2C	0.2501	0.0342	0.4169	0.147*
C3	0.0128 (4)	0.1701 (3)	0.4649 (2)	0.1067 (14)
H3A	−0.0026	0.2343	0.4571	0.160*
H3B	0.0038	0.1560	0.5160	0.160*
H3C	−0.0467	0.1347	0.4371	0.160*
C4	0.1436 (4)	0.1469 (2)	0.44047 (16)	0.0686 (10)
C5	0.1046 (4)	0.1604 (2)	0.30812 (18)	0.0623 (9)
C6	0.0904 (4)	0.1711 (2)	0.17744 (16)	0.0688 (10)
H6A	0.1042	0.2185	0.1409	0.083*
H6B	0.0003	0.1629	0.1829	0.083*
C7	0.1484 (3)	0.0821 (2)	0.15127 (17)	0.0747 (11)
H7A	0.2365	0.0922	0.1400	0.090*
H7B	0.1437	0.0368	0.1902	0.090*
C8	0.0838 (4)	0.0459 (3)	0.08533 (19)	0.0719 (10)
C9	0.2554 (4)	0.2605 (2)	0.24626 (18)	0.0762 (10)
H9A	0.2844	0.2675	0.1962	0.091*
H9B	0.3220	0.2308	0.2738	0.091*
C10	0.2318 (4)	0.3548 (2)	0.27853 (18)	0.0762 (11)
H10A	0.1970	0.3475	0.3273	0.091*
H10B	0.3116	0.3865	0.2833	0.091*
C11	0.1451 (4)	0.4125 (2)	0.2344 (2)	0.0732 (11)

	U11	U22	U33	U12	U13	U23
O1	0.0897 (19)	0.0642 (13)	0.0588 (12)	−0.0127 (13)	−0.0146 (12)	−0.0004 (10)
O2	0.097 (2)	0.0806 (16)	0.0750 (16)	−0.0276 (16)	−0.0109 (14)	−0.0061 (12)
O3	0.152 (3)	0.0724 (19)	0.0737 (17)	0.0156 (18)	−0.0244 (17)	−0.0096 (14)
O4	0.164 (3)	0.0759 (17)	0.0831 (17)	0.0102 (17)	−0.0439 (18)	−0.0010 (15)
O5	0.094 (2)	0.0750 (17)	0.0803 (16)	0.0181 (15)	−0.0104 (14)	0.0071 (14)
O6	0.153 (3)	0.0836 (18)	0.106 (2)	0.0274 (18)	−0.053 (2)	−0.0026 (16)
N1	0.078 (2)	0.0626 (15)	0.0595 (16)	−0.0032 (16)	−0.0056 (15)	0.0027 (14)
C1	0.094 (3)	0.103 (3)	0.073 (2)	0.004 (2)	−0.017 (2)	−0.012 (2)
C2	0.132 (4)	0.072 (3)	0.090 (3)	0.002 (3)	−0.012 (3)	0.015 (2)
C3	0.091 (4)	0.132 (3)	0.097 (3)	0.009 (3)	0.013 (3)	−0.017 (3)
C4	0.080 (3)	0.069 (2)	0.0572 (18)	0.002 (2)	−0.0009 (18)	−0.0036 (17)
C5	0.066 (3)	0.054 (2)	0.067 (2)	−0.0066 (19)	−0.0100 (19)	−0.0035 (17)
C6	0.080 (3)	0.065 (2)	0.060 (2)	0.011 (2)	−0.0078 (17)	−0.0011 (16)
C7	0.073 (3)	0.082 (2)	0.069 (2)	0.014 (2)	−0.0123 (18)	−0.0100 (18)
C8	0.081 (3)	0.071 (3)	0.064 (2)	0.025 (2)	−0.0029 (19)	−0.009 (2)
C9	0.069 (3)	0.075 (2)	0.084 (2)	0.005 (2)	−0.0019 (19)	0.014 (2)
C10	0.078 (3)	0.064 (2)	0.087 (2)	−0.010 (2)	−0.023 (2)	0.0155 (17)
C11	0.087 (3)	0.062 (2)	0.071 (2)	−0.006 (2)	−0.011 (2)	0.0116 (19)

O1—C5	1.331 (4)	C2—H2B	0.96
O1—C4	1.482 (3)	C2—H2C	0.96
O2—C5	1.229 (4)	C3—C4	1.499 (5)
O3—C8	1.281 (4)	C3—H3A	0.96
O3—H3O	0.98 (5)	C3—H3B	0.96
O4—C8	1.199 (4)	C3—H3C	0.96
O5—C11	1.315 (4)	C6—C7	1.513 (4)
O5—H5O	0.94 (5)	C6—H6A	0.97
O6—C11	1.193 (4)	C6—H6B	0.97
N1—C5	1.331 (4)	C7—C8	1.482 (5)
N1—C6	1.448 (4)	C7—H7A	0.97
N1—C9	1.477 (4)	C7—H7B	0.97
C1—C4	1.514 (5)	C9—C10	1.515 (4)
C1—H1A	0.96	C9—H9A	0.97
C1—H1B	0.96	C9—H9B	0.97
C1—H1C	0.96	C10—C11	1.486 (5)
C2—C4	1.508 (4)	C10—H10A	0.97
C2—H2A	0.96	C10—H10B	0.97
C5—O1—C4	121.8 (3)	O1—C5—N1	113.5 (3)
C8—O3—H3O	108 (2)	N1—C6—C7	111.8 (3)
C11—O5—H5O	110 (3)	N1—C6—H6A	109.3
C5—N1—C6	119.0 (3)	C7—C6—H6A	109.3
C5—N1—C9	120.9 (3)	N1—C6—H6B	109.3
C6—N1—C9	119.0 (3)	C7—C6—H6B	109.3
C4—C1—H1A	109.5	H6A—C6—H6B	107.9
C4—C1—H1B	109.5	C8—C7—C6	111.8 (3)
H1A—C1—H1B	109.5	C8—C7—H7A	109.2
C4—C1—H1C	109.5	C6—C7—H7A	109.2
H1A—C1—H1C	109.5	C8—C7—H7B	109.2
H1B—C1—H1C	109.5	C6—C7—H7B	109.2
C4—C2—H2A	109.5	H7A—C7—H7B	107.9
C4—C2—H2B	109.5	O4—C8—O3	122.6 (3)
H2A—C2—H2B	109.5	O4—C8—C7	122.5 (4)
C4—C2—H2C	109.5	O3—C8—C7	114.9 (3)
H2A—C2—H2C	109.5	N1—C9—C10	113.5 (3)
H2B—C2—H2C	109.5	N1—C9—H9A	108.9
C4—C3—H3A	109.5	C10—C9—H9A	108.9
C4—C3—H3B	109.5	N1—C9—H9B	108.9
H3A—C3—H3B	109.5	C10—C9—H9B	108.9
C4—C3—H3C	109.5	H9A—C9—H9B	107.7
H3A—C3—H3C	109.5	C11—C10—C9	113.9 (3)
H3B—C3—H3C	109.5	C11—C10—H10A	108.8
O1—C4—C3	110.5 (3)	C9—C10—H10A	108.8
O1—C4—C2	109.4 (3)	C11—C10—H10B	108.8
C3—C4—C2	113.4 (3)	C9—C10—H10B	108.8
O1—C4—C1	101.2 (3)	H10A—C10—H10B	107.7
C3—C4—C1	110.4 (3)	O6—C11—O5	122.7 (3)
C2—C4—C1	111.3 (3)	O6—C11—C10	125.6 (3)
O2—C5—O1	123.5 (3)	O5—C11—C10	111.6 (3)
O2—C5—N1	123.0 (3)
C5—O1—C4—C3	−63.2 (4)	C9—N1—C6—C7	89.6 (3)
C5—O1—C4—C2	62.3 (4)	N1—C6—C7—C8	173.1 (3)
C5—O1—C4—C1	179.9 (3)	C6—C7—C8—O4	39.8 (5)
C4—O1—C5—O2	4.4 (5)	C6—C7—C8—O3	−142.1 (3)
C4—O1—C5—N1	−177.7 (3)	C5—N1—C9—C10	−76.4 (4)
C6—N1—C5—O2	−8.8 (5)	C6—N1—C9—C10	115.9 (3)
C9—N1—C5—O2	−176.5 (3)	N1—C9—C10—C11	−67.1 (4)
C6—N1—C5—O1	173.3 (3)	C9—C10—C11—O6	−5.7 (6)
C9—N1—C5—O1	5.6 (4)	C9—C10—C11—O5	177.0 (3)
C5—N1—C6—C7	−78.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O4i	0.98 (5)	1.68 (5)	2.653 (4)	174 (4)
O5—H5O···O2ii	0.94 (5)	1.70 (5)	2.628 (3)	168 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3O⋯O4i	0.98 (5)	1.68 (5)	2.653 (4)	174 (4)
O5—H5O⋯O2ii	0.94 (5)	1.70 (5)	2.628 (3)	168 (4)

Symmetry codes: (i) ; (ii) .