Methyl 3-[(1-adamantylcarbon-yloxy)amino-carbon-yl]propanoate.

In the title compound, C(16)H(23)NO(5), the H-N-O-C torsion angle is 98.6 (1)°, which is of a similar magnitude to other N,O-diacyl-hydroxy-lamines. The N-O distance is 1.4029 (14) Å, which is similar to the N-O distance in other N,O-diacyl-hydroxy-lamines. In the crystal, intermolecular N-H⋯O hydrogen bonds generate chains of molecules.

Related literature

For the biological activity of compounds related to N,O-diacyl­hydroxy­lamines, see: Pelto & Pratt (2008 ▶). For linear N,O-diacyl­hydroxy­lamines, see: Göttlicher & Ochsenreiter (1974 ▶); Schraml et al. (2004 ▶); Baert et al. (1984 ▶); Masui et al. (1983 ▶); Grassi et al. (2002 ▶); Buscemi et al. (2006 ▶). For cyclic N,O-diacyl­hydroxy­lamines, see: Kongprakaiwoot et al. (2008 ▶). For a precursor of the title compound, see: Liu et al. (2009 ▶).

Experimental

Crystal data

C16H23NO5

M = 309.35

Orthorhombic,

a = 15.7837 (5) Å

b = 21.0715 (7) Å

c = 9.5341 (3) Å

V = 3170.91 (18) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 150 K

0.30 × 0.20 × 0.15 mm

Data collection

Bruker APEXII-FR591 diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.851, T max = 0.981

22952 measured reflections

4586 independent reflections

2890 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.132

S = 1.04

4586 reflections

200 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT and XPREP (Bruker, 2003 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶), WinGX32 (Farrugia, 1999 ▶), POV-RAY (Cason, 2002 ▶) and WebLab ViewerPro (Molecular Simulations, 2000 ▶); software used to prepare material for publication: enCIFer (Allen et al., 2004 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809024210/bg2266sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809024210/bg2266Isup2.hkl

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

C16H23NO5	F(000) = 1328
Mr = 309.35	Dx = 1.296 Mg m−3
Orthorhombic, Pccn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2ac	Cell parameters from 3869 reflections
a = 15.7837 (5) Å	θ = 2.8–30.0°
b = 21.0715 (7) Å	µ = 0.10 mm−1
c = 9.5341 (3) Å	T = 150 K
V = 3170.91 (18) Å3	Block, colourless
Z = 8	0.30 × 0.20 × 0.15 mm

Bruker APEXII-FR591 diffractometer	4586 independent reflections
Radiation source: rotating anode	2890 reflections with I > 2σ(I)
graphite	Rint = 0.036
ω+φ scans	θmax = 30.0°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	h = −22→22
Tmin = 0.851, Tmax = 0.981	k = −26→29
22952 measured reflections	l = −13→11

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0599P)2 + 0.4178P] where P = (Fo2 + 2Fc2)/3
4586 reflections	(Δ/σ)max < 0.001
200 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

Experimental. The crystal was coated in Exxon Paratone N hydrocarbon oil and mounted on a thin mohair fibre attached to a copper pin. Upon mounting on the diffractometer, the crystal was quenched to 150(K) under a cold nitrogen gas stream supplied by an Oxford Cryosystems Cryostream and data were collected at this temperature.

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
C1	−0.10511 (9)	0.03188 (7)	0.34190 (19)	0.0397 (4)
H1A	−0.1286	0.0521	0.4259	0.060*
H1B	−0.1195	−0.0134	0.3422	0.060*
H1C	−0.1289	0.0520	0.2580	0.060*
C2	0.01542 (9)	0.09834 (6)	0.33007 (15)	0.0282 (3)
C3	0.11059 (9)	0.09992 (7)	0.32346 (18)	0.0347 (3)
H3A	0.1293	0.0852	0.2299	0.042*
H3B	0.1339	0.0704	0.3944	0.042*
C4	0.14536 (9)	0.16607 (7)	0.34972 (19)	0.0395 (4)
H4A	0.1174	0.1965	0.2855	0.047*
H4B	0.1321	0.1790	0.4471	0.047*
C5	0.24014 (10)	0.16868 (7)	0.32743 (19)	0.0381 (4)
C6	0.41331 (9)	0.12429 (6)	0.41915 (16)	0.0285 (3)
C7	0.50576 (8)	0.13370 (5)	0.38462 (14)	0.0217 (3)
C8	0.51335 (8)	0.13881 (6)	0.22281 (15)	0.0264 (3)
H8A	0.4889	0.1005	0.1782	0.032*
H8B	0.4816	0.1763	0.1890	0.032*
C9	0.60700 (8)	0.14499 (6)	0.18337 (15)	0.0272 (3)
H9	0.6124	0.1480	0.0791	0.033*
C10	0.64442 (8)	0.20472 (6)	0.25077 (15)	0.0277 (3)
H10A	0.7048	0.2090	0.2240	0.033*
H10B	0.6137	0.2427	0.2167	0.033*
C11	0.63684 (8)	0.20033 (6)	0.40991 (15)	0.0271 (3)
H11	0.6612	0.2395	0.4533	0.032*
C12	0.54299 (8)	0.19452 (6)	0.45073 (16)	0.0269 (3)
H12A	0.5114	0.2321	0.4169	0.032*
H12B	0.5375	0.1926	0.5541	0.032*
C13	0.55512 (8)	0.07550 (6)	0.43587 (16)	0.0279 (3)
H13A	0.5313	0.0366	0.3930	0.034*
H13B	0.5499	0.0718	0.5390	0.034*
C14	0.64869 (9)	0.08217 (6)	0.39547 (17)	0.0321 (3)
H14	0.6808	0.0442	0.4292	0.039*
C15	0.68529 (9)	0.14227 (7)	0.46296 (18)	0.0358 (4)
H15A	0.6804	0.1394	0.5663	0.043*
H15B	0.7460	0.1463	0.4388	0.043*
C16	0.65534 (9)	0.08664 (6)	0.23537 (17)	0.0341 (4)
H16A	0.7156	0.0898	0.2075	0.041*
H16B	0.6313	0.0479	0.1922	0.041*
N1	0.28451 (7)	0.17669 (6)	0.44376 (15)	0.0376 (3)
H1	0.2595	0.1786	0.5262	0.045*
O1	−0.01378 (6)	0.03915 (5)	0.34139 (12)	0.0391 (3)
O2	−0.02969 (6)	0.14408 (5)	0.32255 (14)	0.0420 (3)
O3	0.27389 (7)	0.16496 (7)	0.21147 (14)	0.0595 (4)
O4	0.37279 (6)	0.18202 (4)	0.43133 (12)	0.0349 (3)
O5	0.37653 (7)	0.07535 (5)	0.43361 (14)	0.0506 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0367 (8)	0.0359 (7)	0.0464 (10)	−0.0018 (6)	0.0100 (8)	−0.0004 (7)
C2	0.0327 (7)	0.0296 (6)	0.0223 (7)	0.0045 (5)	0.0017 (6)	−0.0017 (6)
C3	0.0298 (7)	0.0359 (7)	0.0384 (9)	0.0084 (6)	0.0016 (7)	−0.0012 (6)
C4	0.0256 (7)	0.0431 (8)	0.0497 (11)	0.0040 (6)	−0.0011 (7)	−0.0097 (7)
C5	0.0289 (7)	0.0449 (8)	0.0406 (10)	0.0021 (6)	0.0015 (8)	−0.0026 (7)
C6	0.0271 (7)	0.0301 (6)	0.0281 (8)	−0.0026 (5)	0.0018 (6)	0.0000 (6)
C7	0.0217 (6)	0.0227 (6)	0.0206 (7)	−0.0040 (4)	0.0008 (6)	0.0009 (5)
C8	0.0281 (7)	0.0299 (6)	0.0211 (7)	−0.0070 (5)	−0.0028 (6)	0.0010 (5)
C9	0.0313 (7)	0.0299 (6)	0.0203 (7)	−0.0075 (5)	0.0042 (6)	0.0012 (5)
C10	0.0273 (6)	0.0239 (6)	0.0318 (9)	−0.0060 (5)	0.0018 (6)	0.0058 (5)
C11	0.0270 (6)	0.0253 (6)	0.0289 (8)	−0.0078 (5)	−0.0055 (6)	−0.0005 (5)
C12	0.0305 (7)	0.0268 (6)	0.0234 (8)	−0.0031 (5)	−0.0018 (6)	−0.0027 (5)
C13	0.0306 (7)	0.0238 (6)	0.0294 (8)	−0.0035 (5)	0.0021 (7)	0.0074 (5)
C14	0.0264 (7)	0.0267 (6)	0.0433 (10)	0.0033 (5)	−0.0003 (7)	0.0103 (6)
C15	0.0259 (7)	0.0435 (8)	0.0382 (9)	−0.0039 (6)	−0.0099 (7)	0.0099 (7)
C16	0.0304 (7)	0.0259 (6)	0.0459 (10)	−0.0028 (5)	0.0123 (7)	−0.0021 (6)
N1	0.0215 (6)	0.0512 (7)	0.0401 (8)	0.0015 (5)	0.0037 (6)	−0.0063 (6)
O1	0.0342 (5)	0.0295 (5)	0.0538 (8)	0.0035 (4)	0.0041 (5)	−0.0012 (5)
O2	0.0312 (5)	0.0327 (5)	0.0621 (8)	0.0069 (4)	0.0012 (6)	0.0032 (5)
O3	0.0365 (7)	0.1062 (11)	0.0358 (8)	0.0027 (7)	0.0009 (6)	0.0004 (7)
O4	0.0213 (5)	0.0350 (5)	0.0485 (7)	0.0011 (4)	0.0008 (5)	−0.0027 (5)
O5	0.0314 (5)	0.0362 (6)	0.0841 (10)	−0.0085 (4)	0.0154 (6)	0.0045 (6)

C1—O1	1.4498 (17)	C9—C16	1.5296 (19)
C1—H1A	0.9800	C9—C10	1.5316 (18)
C1—H1B	0.9800	C9—H9	1.0000
C1—H1C	0.9800	C10—C11	1.525 (2)
C2—O2	1.2005 (16)	C10—H10A	0.9900
C2—O1	1.3340 (16)	C10—H10B	0.9900
C2—C3	1.5038 (19)	C11—C15	1.5289 (19)
C3—C4	1.519 (2)	C11—C12	1.5364 (18)
C3—H3A	0.9900	C11—H11	1.0000
C3—H3B	0.9900	C12—H12A	0.9900
C4—C5	1.512 (2)	C12—H12B	0.9900
C4—H4A	0.9900	C13—C14	1.5327 (19)
C4—H4B	0.9900	C13—H13A	0.9900
C5—O3	1.230 (2)	C13—H13B	0.9900
C5—N1	1.322 (2)	C14—C16	1.533 (2)
C6—O5	1.1913 (16)	C14—C15	1.533 (2)
C6—O4	1.3792 (16)	C14—H14	1.0000
C6—C7	1.5090 (18)	C15—H15A	0.9900
C7—C13	1.5329 (17)	C15—H15B	0.9900
C7—C12	1.5443 (17)	C16—H16A	0.9900
C7—C8	1.5510 (19)	C16—H16B	0.9900
C8—C9	1.5308 (18)	N1—O4	1.4029 (14)
C8—H8A	0.9900	N1—H1	0.8800
C8—H8B	0.9900
O1—C1—H1A	109.5	C11—C10—H10A	109.7
O1—C1—H1B	109.5	C9—C10—H10A	109.7
H1A—C1—H1B	109.5	C11—C10—H10B	109.7
O1—C1—H1C	109.5	C9—C10—H10B	109.7
H1A—C1—H1C	109.5	H10A—C10—H10B	108.2
H1B—C1—H1C	109.5	C10—C11—C15	109.78 (12)
O2—C2—O1	123.41 (13)	C10—C11—C12	109.42 (11)
O2—C2—C3	124.90 (13)	C15—C11—C12	109.55 (11)
O1—C2—C3	111.67 (11)	C10—C11—H11	109.4
C2—C3—C4	111.98 (11)	C15—C11—H11	109.4
C2—C3—H3A	109.2	C12—C11—H11	109.4
C4—C3—H3A	109.2	C11—C12—C7	109.24 (11)
C2—C3—H3B	109.2	C11—C12—H12A	109.8
C4—C3—H3B	109.2	C7—C12—H12A	109.8
H3A—C3—H3B	107.9	C11—C12—H12B	109.8
C5—C4—C3	111.57 (12)	C7—C12—H12B	109.8
C5—C4—H4A	109.3	H12A—C12—H12B	108.3
C3—C4—H4A	109.3	C7—C13—C14	109.65 (10)
C5—C4—H4B	109.3	C7—C13—H13A	109.7
C3—C4—H4B	109.3	C14—C13—H13A	109.7
H4A—C4—H4B	108.0	C7—C13—H13B	109.7
O3—C5—N1	122.19 (14)	C14—C13—H13B	109.7
O3—C5—C4	123.55 (15)	H13A—C13—H13B	108.2
N1—C5—C4	114.25 (15)	C13—C14—C16	108.77 (12)
O5—C6—O4	121.84 (12)	C13—C14—C15	109.46 (12)
O5—C6—C7	127.62 (12)	C16—C14—C15	109.96 (11)
O4—C6—C7	110.54 (10)	C13—C14—H14	109.5
C6—C7—C13	108.46 (10)	C16—C14—H14	109.5
C6—C7—C12	112.83 (11)	C15—C14—H14	109.5
C13—C7—C12	109.90 (11)	C11—C15—C14	109.49 (11)
C6—C7—C8	107.50 (11)	C11—C15—H15A	109.8
C13—C7—C8	109.47 (11)	C14—C15—H15A	109.8
C12—C7—C8	108.61 (10)	C11—C15—H15B	109.8
C9—C8—C7	108.95 (11)	C14—C15—H15B	109.8
C9—C8—H8A	109.9	H15A—C15—H15B	108.2
C7—C8—H8A	109.9	C9—C16—C14	109.75 (11)
C9—C8—H8B	109.9	C9—C16—H16A	109.7
C7—C8—H8B	109.9	C14—C16—H16A	109.7
H8A—C8—H8B	108.3	C9—C16—H16B	109.7
C16—C9—C8	109.49 (10)	C14—C16—H16B	109.7
C16—C9—C10	109.40 (12)	H16A—C16—H16B	108.2
C8—C9—C10	109.83 (11)	C5—N1—O4	117.73 (13)
C16—C9—H9	109.4	C5—N1—H1	121.1
C8—C9—H9	109.4	O4—N1—H1	121.1
C10—C9—H9	109.4	C2—O1—C1	116.27 (11)
C11—C10—C9	109.72 (10)	C6—O4—N1	113.40 (10)
O2—C2—C3—C4	17.1 (2)	C13—C7—C12—C11	58.97 (15)
O1—C2—C3—C4	−164.72 (13)	C8—C7—C12—C11	−60.76 (14)
C2—C3—C4—C5	−173.84 (14)	C6—C7—C13—C14	177.11 (12)
C3—C4—C5—O3	70.9 (2)	C12—C7—C13—C14	−59.12 (15)
C3—C4—C5—N1	−110.41 (16)	C8—C7—C13—C14	60.09 (14)
O5—C6—C7—C13	−26.1 (2)	C7—C13—C14—C16	−60.43 (14)
O4—C6—C7—C13	154.74 (12)	C7—C13—C14—C15	59.74 (16)
O5—C6—C7—C12	−148.06 (16)	C10—C11—C15—C14	−59.45 (15)
O4—C6—C7—C12	32.74 (16)	C12—C11—C15—C14	60.73 (16)
O5—C6—C7—C8	92.22 (18)	C13—C14—C15—C11	−60.58 (16)
O4—C6—C7—C8	−86.97 (13)	C16—C14—C15—C11	58.86 (15)
C6—C7—C8—C9	−177.12 (10)	C8—C9—C16—C14	−61.11 (14)
C13—C7—C8—C9	−59.50 (12)	C10—C9—C16—C14	59.30 (14)
C12—C7—C8—C9	60.50 (13)	C13—C14—C16—C9	60.84 (13)
C7—C8—C9—C16	59.84 (14)	C15—C14—C16—C9	−59.02 (14)
C7—C8—C9—C10	−60.31 (13)	O3—C5—N1—O4	1.1 (2)
C16—C9—C10—C11	−59.98 (14)	C4—C5—N1—O4	−177.63 (12)
C8—C9—C10—C11	60.21 (14)	O2—C2—O1—C1	1.0 (2)
C9—C10—C11—C15	60.21 (14)	C3—C2—O1—C1	−177.17 (13)
C9—C10—C11—C12	−60.05 (13)	O5—C6—O4—N1	−7.7 (2)
C10—C11—C12—C7	60.71 (13)	C7—C6—O4—N1	171.54 (11)
C15—C11—C12—C7	−59.69 (15)	C5—N1—O4—C6	−81.34 (16)
C6—C7—C12—C11	−179.84 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3i	0.88	1.87	2.7250 (19)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3i	0.88	1.87	2.7250 (19)	165

Symmetry code: (i) .