1-(tert-But-oxy-carbon-yl)piperidine-4-carb-oxy-lic acid.

In the title compound, C(11)H(19)NO(4), the piperidine ring adopts a chair conformation. In the crystal, mol-ecules are linked by inter-molecular O-H⋯O and C-H⋯O hydrogen bonds, forming a layer parallel to the bc plane.

Related literature

For general background and application of helical peptides, see: Albrecht & Stortz (2005 ▶); Garner & Harding (2007 ▶); Wang et al. (2008 ▶); Walensky et al. (2004 ▶); Boal et al. (2007 ▶). For bond-length data, see: Allen et al. (1987 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For stability of the temperature controller used for data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C11H19NO4

M = 229.27

Monoclinic,

a = 10.7006 (3) Å

b = 6.5567 (2) Å

c = 17.9297 (6) Å

β = 104.564 (2)°

V = 1217.54 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.57 × 0.21 × 0.08 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.948, T max = 0.993

5360 measured reflections

2116 independent reflections

1762 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.092

S = 1.07

2116 reflections

152 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811030145/is2754sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811030145/is2754Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811030145/is2754Isup3.cml

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

C11H19NO4	F(000) = 496
Mr = 229.27	Dx = 1.251 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1750 reflections
a = 10.7006 (3) Å	θ = 2.4–28.5°
b = 6.5567 (2) Å	µ = 0.10 mm−1
c = 17.9297 (6) Å	T = 100 K
β = 104.564 (2)°	Plate, colourless
V = 1217.54 (6) Å3	0.57 × 0.21 × 0.08 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	2116 independent reflections
Radiation source: fine-focus sealed tube	1762 reflections with I > 2σ(I)
graphite	Rint = 0.027
φ and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −12→11
Tmin = 0.948, Tmax = 0.993	k = −7→7
5360 measured reflections	l = −16→21

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0362P)2 + 0.3737P] where P = (Fo2 + 2Fc2)/3
2116 reflections	(Δ/σ)max < 0.001
152 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	0.26358 (11)	−0.05214 (18)	0.13924 (6)	0.0249 (3)
O2	0.20095 (11)	0.21800 (16)	0.20083 (6)	0.0229 (3)
O3	0.34156 (12)	−0.53547 (17)	0.46087 (7)	0.0265 (3)
O4	0.35972 (11)	−0.25776 (18)	0.53522 (6)	0.0244 (3)
N1	0.34480 (13)	−0.0015 (2)	0.26790 (7)	0.0188 (3)
C1	0.42896 (16)	−0.1805 (2)	0.27802 (9)	0.0213 (4)
H1A	0.5202	−0.1364	0.2948	0.026*
H1B	0.4167	−0.2525	0.2282	0.026*
C2	0.39922 (16)	−0.3257 (2)	0.33783 (9)	0.0195 (4)
H2A	0.4628	−0.4385	0.3473	0.023*
H2B	0.3123	−0.3855	0.3176	0.023*
C3	0.40397 (15)	−0.2158 (2)	0.41359 (9)	0.0178 (4)
H3A	0.4949	−0.1705	0.4361	0.021*
C4	0.31744 (15)	−0.0254 (2)	0.39936 (9)	0.0186 (4)
H4A	0.2259	−0.0677	0.3819	0.022*
H4B	0.3284	0.0509	0.4482	0.022*
C5	0.35063 (16)	0.1126 (2)	0.33908 (9)	0.0202 (4)
H5A	0.2891	0.2280	0.3280	0.024*
H5B	0.4385	0.1690	0.3591	0.024*
C6	0.26959 (15)	0.0473 (2)	0.19822 (9)	0.0190 (4)
C7	0.10863 (15)	0.2991 (3)	0.13127 (9)	0.0221 (4)
C8	0.06014 (17)	0.4903 (3)	0.16286 (10)	0.0288 (4)
H8A	0.0189	0.4528	0.2039	0.043*
H8B	−0.0027	0.5596	0.1214	0.043*
H8C	0.1330	0.5818	0.1837	0.043*
C9	0.17864 (18)	0.3540 (3)	0.07020 (10)	0.0330 (5)
H9A	0.2538	0.4391	0.0932	0.049*
H9B	0.1201	0.4294	0.0285	0.049*
H9C	0.2073	0.2291	0.0495	0.049*
C10	0.00063 (17)	0.1463 (3)	0.10281 (10)	0.0303 (4)
H10A	−0.0400	0.1137	0.1446	0.046*
H10B	0.0361	0.0215	0.0861	0.046*
H10C	−0.0639	0.2048	0.0594	0.046*
C11	0.36557 (14)	−0.3565 (2)	0.47085 (9)	0.0183 (4)
H1O4	0.333 (2)	−0.340 (4)	0.5652 (13)	0.058 (7)*

	U11	U22	U33	U12	U13	U23
O1	0.0329 (7)	0.0282 (7)	0.0148 (6)	0.0004 (5)	0.0084 (5)	−0.0034 (5)
O2	0.0274 (6)	0.0221 (6)	0.0170 (6)	0.0056 (5)	0.0018 (5)	0.0005 (5)
O3	0.0390 (7)	0.0190 (7)	0.0240 (7)	−0.0008 (5)	0.0125 (6)	0.0008 (5)
O4	0.0353 (7)	0.0226 (7)	0.0175 (6)	−0.0008 (5)	0.0109 (6)	0.0003 (5)
N1	0.0264 (8)	0.0164 (7)	0.0138 (7)	0.0028 (6)	0.0056 (6)	0.0008 (6)
C1	0.0253 (9)	0.0206 (9)	0.0201 (9)	0.0064 (7)	0.0099 (7)	−0.0003 (7)
C2	0.0234 (9)	0.0174 (8)	0.0191 (9)	0.0044 (7)	0.0082 (7)	0.0014 (7)
C3	0.0181 (8)	0.0183 (9)	0.0168 (8)	−0.0005 (7)	0.0043 (7)	0.0012 (7)
C4	0.0218 (9)	0.0189 (9)	0.0153 (8)	0.0010 (7)	0.0051 (7)	−0.0019 (7)
C5	0.0271 (9)	0.0166 (8)	0.0164 (8)	0.0002 (7)	0.0048 (7)	−0.0011 (7)
C6	0.0215 (9)	0.0184 (9)	0.0190 (9)	−0.0017 (7)	0.0086 (7)	0.0033 (7)
C7	0.0205 (9)	0.0276 (9)	0.0159 (8)	0.0012 (7)	0.0006 (7)	0.0046 (7)
C8	0.0264 (10)	0.0274 (10)	0.0296 (10)	0.0053 (8)	0.0017 (8)	0.0026 (8)
C9	0.0311 (10)	0.0395 (11)	0.0297 (10)	0.0074 (9)	0.0101 (8)	0.0152 (9)
C10	0.0257 (10)	0.0341 (11)	0.0295 (10)	−0.0009 (8)	0.0039 (8)	−0.0021 (8)
C11	0.0167 (8)	0.0204 (9)	0.0170 (8)	0.0034 (7)	0.0025 (7)	−0.0003 (7)

O1—C6	1.2303 (18)	C4—C5	1.519 (2)
O2—C6	1.3457 (19)	C4—H4A	0.9900
O2—C7	1.4815 (18)	C4—H4B	0.9900
O3—C11	1.2050 (19)	C5—H5A	0.9900
O4—C11	1.3384 (18)	C5—H5B	0.9900
O4—H1O4	0.86 (2)	C7—C9	1.517 (2)
N1—C6	1.344 (2)	C7—C10	1.518 (2)
N1—C1	1.463 (2)	C7—C8	1.519 (2)
N1—C5	1.4669 (19)	C8—H8A	0.9800
C1—C2	1.526 (2)	C8—H8B	0.9800
C1—H1A	0.9900	C8—H8C	0.9800
C1—H1B	0.9900	C9—H9A	0.9800
C2—C3	1.527 (2)	C9—H9B	0.9800
C2—H2A	0.9900	C9—H9C	0.9800
C2—H2B	0.9900	C10—H10A	0.9800
C3—C11	1.512 (2)	C10—H10B	0.9800
C3—C4	1.537 (2)	C10—H10C	0.9800
C3—H3A	1.0000
C6—O2—C7	121.57 (12)	C4—C5—H5B	109.6
C11—O4—H1O4	109.2 (15)	H5A—C5—H5B	108.1
C6—N1—C1	120.84 (13)	O1—C6—N1	124.22 (15)
C6—N1—C5	124.88 (13)	O1—C6—O2	124.04 (15)
C1—N1—C5	114.27 (12)	N1—C6—O2	111.74 (13)
N1—C1—C2	110.93 (12)	O2—C7—C9	110.31 (13)
N1—C1—H1A	109.5	O2—C7—C10	109.63 (13)
C2—C1—H1A	109.5	C9—C7—C10	112.73 (15)
N1—C1—H1B	109.5	O2—C7—C8	101.56 (12)
C2—C1—H1B	109.5	C9—C7—C8	110.50 (14)
H1A—C1—H1B	108.0	C10—C7—C8	111.56 (14)
C1—C2—C3	111.36 (13)	C7—C8—H8A	109.5
C1—C2—H2A	109.4	C7—C8—H8B	109.5
C3—C2—H2A	109.4	H8A—C8—H8B	109.5
C1—C2—H2B	109.4	C7—C8—H8C	109.5
C3—C2—H2B	109.4	H8A—C8—H8C	109.5
H2A—C2—H2B	108.0	H8B—C8—H8C	109.5
C11—C3—C2	111.22 (13)	C7—C9—H9A	109.5
C11—C3—C4	110.67 (12)	C7—C9—H9B	109.5
C2—C3—C4	110.60 (13)	H9A—C9—H9B	109.5
C11—C3—H3A	108.1	C7—C9—H9C	109.5
C2—C3—H3A	108.1	H9A—C9—H9C	109.5
C4—C3—H3A	108.1	H9B—C9—H9C	109.5
C5—C4—C3	111.29 (12)	C7—C10—H10A	109.5
C5—C4—H4A	109.4	C7—C10—H10B	109.5
C3—C4—H4A	109.4	H10A—C10—H10B	109.5
C5—C4—H4B	109.4	C7—C10—H10C	109.5
C3—C4—H4B	109.4	H10A—C10—H10C	109.5
H4A—C4—H4B	108.0	H10B—C10—H10C	109.5
N1—C5—C4	110.43 (12)	O3—C11—O4	122.99 (15)
N1—C5—H5A	109.6	O3—C11—C3	125.29 (14)
C4—C5—H5A	109.6	O4—C11—C3	111.72 (13)
N1—C5—H5B	109.6
C6—N1—C1—C2	−123.01 (15)	C1—N1—C6—O2	−179.20 (13)
C5—N1—C1—C2	56.56 (17)	C5—N1—C6—O2	1.3 (2)
N1—C1—C2—C3	−53.55 (17)	C7—O2—C6—O1	1.2 (2)
C1—C2—C3—C11	176.11 (13)	C7—O2—C6—N1	−178.49 (13)
C1—C2—C3—C4	52.71 (17)	C6—O2—C7—C9	−61.40 (18)
C11—C3—C4—C5	−177.27 (13)	C6—O2—C7—C10	63.30 (17)
C2—C3—C4—C5	−53.56 (17)	C6—O2—C7—C8	−178.59 (13)
C6—N1—C5—C4	122.38 (16)	C2—C3—C11—O3	4.2 (2)
C1—N1—C5—C4	−57.18 (17)	C4—C3—C11—O3	127.55 (17)
C3—C4—C5—N1	54.71 (17)	C2—C3—C11—O4	−175.19 (13)
C1—N1—C6—O1	1.1 (2)	C4—C3—C11—O4	−51.83 (17)
C5—N1—C6—O1	−178.39 (14)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H1O4···O1i	0.86 (2)	1.82 (2)	2.6562 (16)	164 (2)
C5—H5B···O4ii	0.99	2.56	3.476 (2)	154.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H1O4⋯O1i	0.86 (2)	1.82 (2)	2.6562 (16)	164 (2)
C5—H5B⋯O4ii	0.99	2.56	3.476 (2)	154

Symmetry codes: (i) ; (ii) .