2-[(tert-But­oxy­carbonyl­amino)­oxy]acetic acid

Zhang, J.-Y.; Tong, Y.; Wang, S.

doi:10.1107/S1600536811031990

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2324

doi:10.1107/S1600536811031990

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2-[(tert-Butoxycarbonylamino)oxy]acetic acid

Jing-Yu Zhang,^a ^* Yan Tong ^b and Shengqi Wang ^a

^aSchool of Pharmacy Henan University of Traditional Chinese Medicine, Zhengzhou 450008, People's Republic of China, and ^bDepartment of Quality Detection and Management, Zhengzhou College of Animal Husbandry Engineering, Zhengzhou 450011, People's Republic of China
^*Correspondence e-mail: jyzhang2004@126.com

(Received 1 August 2011; accepted 8 August 2011; online 11 August 2011)

The title compound, C₇H₁₃NO₅, was prepared by the condensation of O-(carboxymethyl)hydroxylamine and (Boc)₂O (Boc = butoxycarbonyl).In the crystal, molecules are linked by weak intermolecular N—H⋯O hydrogen bonds.

Related literature

For applications and structural studies of N-Boc-O-(carboxymethyl)hydroxylamine, see: Vandersse et al. (2003 ); Deroo et al., 2003 .

Experimental

Crystal data

C₇H₁₃NO₅
M_r = 191.18
Monoclinic, P 2₁ /c
a = 5.9973 (5) Å
b = 10.1292 (13) Å
c = 15.6445 (17) Å
β = 90.570 (1)°
V = 950.32 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 298 K
0.43 × 0.33 × 0.31 mm

Data collection

Siemens SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.953, T_max = 0.966
4733 measured reflections
1670 independent reflections
1073 reflections with I > 2σ(I)
R_int = 0.062

Refinement

R[F² > 2σ(F²)] = 0.068
wR(F²) = 0.210
S = 1.00
1670 reflections
126 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.44 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2ⁱ	0.92 (5)	2.50 (5)	3.413 (4)	174 (4)
Symmetry code: (i) x-1, y, z.

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811031990/lx2198sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811031990/lx2198Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811031990/lx2198Isup3.cml

checkCIF report

Comment top

N–(tert–Butoxycarbonyl)–O– (carboxymethyl)hydroxylamine is an important building block having a broad spectrum of applications in the biochemical fields (Vandersse et al., 2003; Deroo et al., 2003). As a contribution in this filed, we report here the crystal structure of the title compound.

The molecular structure of title compound is shown in Fig. 1. The crystal packing (Fig. 2) is stabilized by weak intermolecular N—H···O hydrogen bonds between the amine H atom and the O atom of the hydroxy group (Table, N1—H1···O2ⁱ).

Related literature top

For applications and structural studies of N-Boc-O-(carboxymethyl)hydroxylamine, see: Vandersse et al. (2003); Deroo et al., 2003.

Experimental top

(Boc)₂O (21.8 g, 0.10 mol) was added to a stirred solution of O–(carboxymethyl)hydroxylamine (9.1 g, 0.10 mol) in dioxane. The mixture was stirred at 303 K for 2 h. Then mixture was concentrated and purified by crystallization from MeOH. Single crystals suitable for X–ray diffraction were prepared by slow evaporation of a solution of the title compound in MeOH at room temperature.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as a small spheres of arbitrary radius.
	Fig. 2. A view of the N—H···O interactions (dotted lines) in the crystal structure of the title compound.

2-[(tert-Butoxycarbonylamino)oxy]acetic acid top

Crystal data top

C₇H₁₃NO₅	F(000) = 408
M_r = 191.18	D_x = 1.336 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1234 reflections
a = 5.9973 (5) Å	θ = 2.4–22.0°
b = 10.1292 (13) Å	µ = 0.11 mm⁻¹
c = 15.6445 (17) Å	T = 298 K
β = 90.570 (1)°	Block, colorless
V = 950.32 (18) Å³	0.43 × 0.33 × 0.31 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	1670 independent reflections
Radiation source: fine-focus sealed tube	1073 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.062
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→7
T_min = 0.953, T_max = 0.966	k = −9→12
4733 measured reflections	l = −18→18

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.068	Hydrogen site location: difference Fourier map
wR(F²) = 0.210	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.112P)² + 0.8197P] where P = (F_o² + 2F_c²)/3
1670 reflections	(Δ/σ)_max < 0.001
126 parameters	Δρ_max = 0.48 e Å⁻³
0 restraints	Δρ_min = −0.44 e Å⁻³

Crystal data top

C₇H₁₃NO₅	V = 950.32 (18) Å³
M_r = 191.18	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.9973 (5) Å	µ = 0.11 mm⁻¹
b = 10.1292 (13) Å	T = 298 K
c = 15.6445 (17) Å	0.43 × 0.33 × 0.31 mm
β = 90.570 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	1670 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1073 reflections with I > 2σ(I)
T_min = 0.953, T_max = 0.966	R_int = 0.062
4733 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.068	0 restraints
wR(F²) = 0.210	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.48 e Å⁻³
1670 reflections	Δρ_min = −0.44 e Å⁻³
126 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.6083 (5)	0.1502 (3)	0.0709 (2)	0.0435 (8)
O1	0.8143 (4)	0.3814 (3)	−0.00926 (18)	0.0496 (8)
O2	1.1753 (4)	0.3574 (3)	0.02405 (19)	0.0520 (8)
H2	1.2247	0.3245	0.0682	0.078*
O3	0.7431 (4)	0.1152 (2)	0.00116 (15)	0.0437 (7)
O4	0.3937 (4)	0.0832 (3)	0.17426 (16)	0.0444 (7)
O5	0.6762 (5)	−0.0506 (3)	0.13138 (17)	0.0521 (8)
C1	0.9751 (6)	0.3117 (4)	0.0088 (2)	0.0370 (9)
C2	0.9609 (6)	0.1647 (4)	0.0151 (2)	0.0416 (9)
H2A	1.0601	0.1258	−0.0265	0.050*
H2B	1.0122	0.1375	0.0715	0.050*
C3	0.5677 (6)	0.0477 (4)	0.1261 (2)	0.0374 (9)
C4	0.3312 (6)	0.0044 (4)	0.2499 (2)	0.0376 (9)
C5	0.1486 (8)	0.0912 (5)	0.2878 (3)	0.0669 (13)
H5A	0.2111	0.1745	0.3047	0.100*
H5B	0.0867	0.0481	0.3368	0.100*
H5C	0.0334	0.1053	0.2458	0.100*
C6	0.2369 (8)	−0.1253 (5)	0.2217 (3)	0.0641 (13)
H6A	0.1142	−0.1105	0.1830	0.096*
H6B	0.1858	−0.1734	0.2706	0.096*
H6C	0.3502	−0.1754	0.1934	0.096*
C7	0.5264 (7)	−0.0085 (5)	0.3105 (3)	0.0609 (13)
H7A	0.6414	−0.0598	0.2841	0.091*
H7B	0.4792	−0.0515	0.3619	0.091*
H7C	0.5832	0.0777	0.3242	0.091*
H1	0.488 (8)	0.201 (5)	0.055 (3)	0.073 (15)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0441 (19)	0.0384 (18)	0.0481 (18)	0.0007 (15)	0.0160 (15)	0.0042 (15)
O1	0.0395 (15)	0.0400 (16)	0.0693 (18)	−0.0018 (12)	−0.0014 (13)	0.0117 (14)
O2	0.0406 (16)	0.0477 (17)	0.0673 (19)	−0.0051 (13)	−0.0115 (13)	0.0054 (14)
O3	0.0464 (15)	0.0420 (16)	0.0431 (15)	−0.0094 (12)	0.0127 (12)	−0.0056 (12)
O4	0.0411 (15)	0.0457 (16)	0.0467 (15)	0.0067 (12)	0.0124 (12)	0.0116 (12)
O5	0.0501 (16)	0.0496 (17)	0.0569 (17)	0.0137 (14)	0.0129 (13)	0.0108 (14)
C1	0.039 (2)	0.039 (2)	0.0332 (18)	−0.0018 (17)	0.0045 (15)	0.0012 (15)
C2	0.039 (2)	0.037 (2)	0.049 (2)	−0.0025 (16)	0.0072 (16)	0.0003 (17)
C3	0.0346 (19)	0.038 (2)	0.040 (2)	−0.0018 (17)	0.0060 (16)	0.0007 (17)
C4	0.0320 (19)	0.046 (2)	0.0347 (19)	−0.0039 (16)	0.0068 (15)	0.0084 (15)
C5	0.059 (3)	0.082 (4)	0.059 (3)	0.010 (3)	0.019 (2)	0.008 (2)
C6	0.068 (3)	0.059 (3)	0.065 (3)	−0.017 (2)	0.006 (2)	0.009 (2)
C7	0.047 (2)	0.082 (4)	0.053 (3)	−0.007 (2)	−0.002 (2)	0.015 (2)

Geometric parameters (Å, º) top

N1—C3	1.374 (5)	C4—C6	1.496 (6)
N1—O3	1.410 (4)	C4—C7	1.505 (6)
N1—H1	0.92 (5)	C4—C5	1.529 (6)
O1—C1	1.226 (4)	C5—H5A	0.9600
O2—C1	1.306 (4)	C5—H5B	0.9600
O2—H2	0.8200	C5—H5C	0.9600
O3—C2	1.414 (4)	C6—H6A	0.9600
O4—C3	1.342 (4)	C6—H6B	0.9600
O4—C4	1.479 (4)	C6—H6C	0.9600
O5—C3	1.192 (4)	C7—H7A	0.9600
C1—C2	1.496 (5)	C7—H7B	0.9600
C2—H2A	0.9700	C7—H7C	0.9600
C2—H2B	0.9700

C3—N1—O3	113.8 (3)	O4—C4—C5	100.9 (3)
C3—N1—H1	117 (3)	C6—C4—C5	110.4 (3)
O3—N1—H1	113 (3)	C7—C4—C5	111.1 (4)
C1—O2—H2	109.5	C4—C5—H5A	109.5
N1—O3—C2	109.1 (3)	C4—C5—H5B	109.5
C3—O4—C4	120.6 (3)	H5A—C5—H5B	109.5
O1—C1—O2	123.9 (4)	C4—C5—H5C	109.5
O1—C1—C2	122.9 (3)	H5A—C5—H5C	109.5
O2—C1—C2	113.2 (3)	H5B—C5—H5C	109.5
O3—C2—C1	113.3 (3)	C4—C6—H6A	109.5
O3—C2—H2A	108.9	C4—C6—H6B	109.5
C1—C2—H2A	108.9	H6A—C6—H6B	109.5
O3—C2—H2B	108.9	C4—C6—H6C	109.5
C1—C2—H2B	108.9	H6A—C6—H6C	109.5
H2A—C2—H2B	107.7	H6B—C6—H6C	109.5
O5—C3—O4	127.7 (3)	C4—C7—H7A	109.5
O5—C3—N1	125.1 (3)	C4—C7—H7B	109.5
O4—C3—N1	107.1 (3)	H7A—C7—H7B	109.5
O4—C4—C6	109.7 (3)	C4—C7—H7C	109.5
O4—C4—C7	110.4 (3)	H7A—C7—H7C	109.5
C6—C4—C7	113.5 (4)	H7B—C7—H7C	109.5

C3—N1—O3—C2	−103.9 (3)	O3—N1—C3—O5	19.7 (5)
N1—O3—C2—C1	−70.1 (4)	O3—N1—C3—O4	−163.5 (3)
O1—C1—C2—O3	−2.1 (5)	C3—O4—C4—C6	−69.9 (4)
O2—C1—C2—O3	178.3 (3)	C3—O4—C4—C7	56.0 (4)
C4—O4—C3—O5	7.1 (6)	C3—O4—C4—C5	173.6 (3)
C4—O4—C3—N1	−169.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.92 (5)	2.50 (5)	3.413 (4)	174 (4)

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₇H₁₃NO₅
M_r	191.18
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	5.9973 (5), 10.1292 (13), 15.6445 (17)
β (°)	90.570 (1)
V (Å³)	950.32 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.43 × 0.33 × 0.31

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.953, 0.966
No. of measured, independent and observed [I > 2σ(I)] reflections	4733, 1670, 1073
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.068, 0.210, 1.00
No. of reflections	1670
No. of parameters	126
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.44

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.92 (5)	2.50 (5)	3.413 (4)	174 (4)

Symmetry code: (i) x−1, y, z.

Acknowledgements

We gratefully acknowledge financial support from the Doctoral Foundation (BSJJ2009–07) of Henan University of Traditional Chinese Medicine.

References

Deroo, S., Defrancq, E., Moucheron, C., Kirsch-De Mesmaeker, A. & Dumy, P. (2003). Tetrahedron Lett. 44, 8379–8382. CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Vandersse, R., Thevenet, L., Marraud, M., Boggetto, N., Reboud, M. & Corbier, C. (2003). J. Pept. Sci. 9, 282–299. Google Scholar