Dimethyl cis-4-hydroxy-methyl-piperidine-2,6-dicarboxyl-ate.

The heterocyclic core of the title compound, C(10)H(17)NO(5), adopts a chair conformation with its three C substituents positioned equatorially. In the crystal, inter-molecular O-H⋯N hydrogen bonds between neighbouring mol-ecules lead to chains along b. These chains are connected by hydro-phobic inter-actions, forming infinite layers and N-H⋯O=C contacts between mol-ecules of adjacent layers give rise to a three-dimensional structure.

Related literature

For structures of related N-heterocyclic compounds, see: Parkin et al. (2004 ▶). For the synthetic procedure, see: Tang et al. (2006 ▶).

Experimental

Crystal data

C10H17NO5

M = 231.25

Monoclinic,

a = 9.1403 (4) Å

b = 7.9153 (3) Å

c = 16.0199 (6) Å

β = 90.503 (4)°

V = 1158.97 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 150 K

0.35 × 0.25 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

9123 measured reflections

3542 independent reflections

1862 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.146

S = 0.89

3542 reflections

149 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.41 e Å−3

Δρmin = −0.40 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis n class="Disease">RED (Oxford Diffraction, 2007 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810010925/im2176sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810010925/im2176Isup2.hkl

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

C10H17NO5	F(000) = 496
Mr = 231.25	Dx = 1.325 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2439 reflections
a = 9.1403 (4) Å	θ = 3.6–31.2°
b = 7.9153 (3) Å	µ = 0.11 mm−1
c = 16.0199 (6) Å	T = 150 K
β = 90.503 (4)°	Prism, colourless
V = 1158.97 (8) Å3	0.35 × 0.25 × 0.20 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	1862 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray Source	Rint = 0.045
graphite	θmax = 31.1°, θmin = 3.6°
Detector resolution: 16.1399 pixels mm-1	h = −13→13
Rotation method data acquisition using ω and phi scans	k = −11→11
9123 measured reflections	l = −23→23
3542 independent reflections

Refinement on F2	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.044	w = 1/[σ2(Fo2) + (0.0827P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.146	(Δ/σ)max < 0.001
S = 0.89	Δρmax = 0.41 e Å−3
3542 reflections	Δρmin = −0.40 e Å−3
149 parameters

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

	x	y	z	Uiso*/Ueq
N1	0.74419 (16)	0.02707 (16)	0.01230 (8)	0.0237 (3)
C2	0.64855 (17)	0.13614 (18)	0.06151 (9)	0.0220 (3)
H2	0.5507	0.133	0.0361	0.026*
O4	0.94904 (13)	−0.11150 (15)	−0.09219 (7)	0.0312 (3)
C8	0.85668 (18)	−0.01946 (19)	−0.12238 (10)	0.0249 (3)
C7	0.63717 (18)	0.0686 (2)	0.14932 (9)	0.0255 (3)
O1	0.51869 (14)	0.13296 (16)	0.18655 (7)	0.0320 (3)
C5	0.80958 (17)	0.27664 (19)	−0.07663 (10)	0.0241 (3)
H5A	0.9091	0.2831	−0.0554	0.029*
H5B	0.8093	0.3154	−0.1341	0.029*
C4	0.71060 (17)	0.39036 (18)	−0.02456 (9)	0.0223 (3)
H4	0.6126	0.3887	−0.0498	0.027*
O91	0.67225 (15)	0.67327 (15)	0.02363 (8)	0.0405 (3)
H91	0.7015	0.7712	0.0231	0.061*
O3	0.72305 (16)	−0.02473 (18)	0.18282 (8)	0.0434 (4)
C6	0.75608 (17)	0.09224 (19)	−0.07327 (9)	0.0226 (3)
H6	0.6588	0.0873	−0.0994	0.027*
C3	0.69913 (18)	0.32103 (19)	0.06401 (9)	0.0244 (3)
H3A	0.6298	0.388	0.0954	0.029*
H3B	0.7936	0.3284	0.0918	0.029*
O2	0.83440 (15)	−0.00053 (17)	−0.20437 (7)	0.0370 (3)
C9	0.7656 (2)	0.5714 (2)	−0.02568 (11)	0.0312 (4)
H9A	0.8647	0.576	−0.0036	0.037*
H9B	0.7667	0.6132	−0.0826	0.037*
C10	0.4996 (2)	0.0889 (3)	0.27333 (10)	0.0396 (5)
H10A	0.4118	0.1406	0.2937	0.059*
H10B	0.582	0.1285	0.3053	0.059*
H10C	0.4921	−0.0316	0.2786	0.059*
C11	0.9277 (2)	−0.1006 (3)	−0.25831 (11)	0.0452 (5)
H11A	0.903	−0.0782	−0.3156	0.068*
H11B	0.9136	−0.2184	−0.2467	0.068*
H11C	1.0282	−0.0712	−0.2482	0.068*
H1	0.844 (2)	0.032 (2)	0.0344 (10)	0.029 (5)*

	U11	U22	U33	U12	U13	U23
N1	0.0317 (7)	0.0181 (6)	0.0214 (6)	−0.0003 (5)	0.0046 (5)	0.0005 (5)
C2	0.0248 (7)	0.0212 (7)	0.0200 (7)	0.0011 (6)	0.0032 (5)	0.0000 (6)
O4	0.0339 (7)	0.0266 (6)	0.0333 (6)	0.0032 (5)	0.0035 (5)	−0.0026 (5)
C8	0.0287 (8)	0.0208 (7)	0.0251 (7)	−0.0036 (6)	0.0040 (6)	−0.0041 (6)
C7	0.0321 (8)	0.0213 (7)	0.0232 (7)	−0.0057 (7)	0.0031 (6)	0.0016 (6)
O1	0.0380 (7)	0.0373 (7)	0.0207 (5)	−0.0014 (5)	0.0079 (5)	0.0013 (5)
C5	0.0274 (8)	0.0190 (7)	0.0259 (7)	−0.0013 (6)	0.0064 (6)	0.0014 (6)
C4	0.0253 (7)	0.0184 (7)	0.0231 (7)	−0.0027 (6)	0.0043 (6)	0.0002 (6)
O91	0.0442 (8)	0.0196 (5)	0.0581 (8)	0.0000 (5)	0.0194 (6)	−0.0033 (6)
O3	0.0477 (8)	0.0485 (8)	0.0339 (7)	0.0122 (7)	0.0056 (6)	0.0150 (6)
C6	0.0251 (7)	0.0217 (7)	0.0212 (7)	−0.0027 (6)	0.0033 (5)	−0.0021 (6)
C3	0.0313 (9)	0.0189 (7)	0.0230 (7)	−0.0006 (6)	0.0033 (6)	−0.0009 (6)
O2	0.0438 (7)	0.0435 (7)	0.0237 (6)	0.0123 (6)	0.0059 (5)	−0.0065 (5)
C9	0.0373 (9)	0.0213 (7)	0.0352 (9)	−0.0015 (7)	0.0100 (7)	0.0010 (7)
C10	0.0503 (11)	0.0494 (11)	0.0193 (7)	−0.0053 (9)	0.0072 (7)	0.0037 (8)
C11	0.0501 (12)	0.0546 (12)	0.0312 (9)	0.0183 (10)	0.0096 (8)	−0.0111 (9)

N1—C2	1.4640 (19)	C4—C3	1.526 (2)
N1—C6	1.4696 (19)	C4—H4	0.98
N1—H1	0.98 (2)	O91—C9	1.420 (2)
C2—C7	1.509 (2)	O91—H91	0.82
C2—C3	1.535 (2)	C6—H6	0.98
C2—H2	0.98	C3—H3A	0.97
O4—C8	1.212 (2)	C3—H3B	0.97
C8—O2	1.3358 (19)	O2—C11	1.454 (2)
C8—C6	1.503 (2)	C9—H9A	0.97
C7—O3	1.201 (2)	C9—H9B	0.97
C7—O1	1.341 (2)	C10—H10A	0.96
O1—C10	1.4452 (18)	C10—H10B	0.96
C5—C4	1.529 (2)	C10—H10C	0.96
C5—C6	1.540 (2)	C11—H11A	0.96
C5—H5A	0.97	C11—H11B	0.96
C5—H5B	0.97	C11—H11C	0.96
C4—C9	1.519 (2)
C2—N1—C6	110.16 (12)	N1—C6—C5	113.04 (12)
C2—N1—H1	110.1 (10)	C8—C6—C5	110.08 (12)
C6—N1—H1	104.3 (10)	N1—C6—H6	108.1
N1—C2—C7	109.83 (12)	C8—C6—H6	108.1
N1—C2—C3	113.27 (12)	C5—C6—H6	108.1
C7—C2—C3	109.67 (12)	C4—C3—C2	109.98 (12)
N1—C2—H2	108	C4—C3—H3A	109.7
C7—C2—H2	108	C2—C3—H3A	109.7
C3—C2—H2	108	C4—C3—H3B	109.7
O4—C8—O2	124.00 (14)	C2—C3—H3B	109.7
O4—C8—C6	124.87 (14)	H3A—C3—H3B	108.2
O2—C8—C6	111.10 (14)	C8—O2—C11	115.98 (14)
O3—C7—O1	124.19 (14)	O91—C9—C4	109.19 (13)
O3—C7—C2	125.75 (15)	O91—C9—H9A	109.8
O1—C7—C2	110.01 (13)	C4—C9—H9A	109.8
C7—O1—C10	116.17 (14)	O91—C9—H9B	109.8
C4—C5—C6	110.44 (12)	C4—C9—H9B	109.8
C4—C5—H5A	109.6	H9A—C9—H9B	108.3
C6—C5—H5A	109.6	O1—C10—H10A	109.5
C4—C5—H5B	109.6	O1—C10—H10B	109.5
C6—C5—H5B	109.6	H10A—C10—H10B	109.5
H5A—C5—H5B	108.1	O1—C10—H10C	109.5
C9—C4—C3	112.07 (13)	H10A—C10—H10C	109.5
C9—C4—C5	110.57 (13)	H10B—C10—H10C	109.5
C3—C4—C5	109.96 (13)	O2—C11—H11A	109.5
C9—C4—H4	108	O2—C11—H11B	109.5
C3—C4—H4	108	H11A—C11—H11B	109.5
C5—C4—H4	108	O2—C11—H11C	109.5
C9—O91—H91	109.5	H11A—C11—H11C	109.5
N1—C6—C8	109.41 (13)	H11B—C11—H11C	109.5
C6—N1—C2—C7	−179.88 (13)	O2—C8—C6—N1	159.66 (13)
C6—N1—C2—C3	−56.88 (17)	O4—C8—C6—C5	102.51 (18)
N1—C2—C7—O3	21.3 (2)	O2—C8—C6—C5	−75.56 (17)
C3—C2—C7—O3	−103.81 (18)	C4—C5—C6—N1	−55.54 (18)
N1—C2—C7—O1	−160.97 (13)	C4—C5—C6—C8	−178.22 (13)
C3—C2—C7—O1	73.94 (16)	C9—C4—C3—C2	−177.93 (13)
O3—C7—O1—C10	2.2 (2)	C5—C4—C3—C2	−54.53 (17)
C2—C7—O1—C10	−175.62 (14)	N1—C2—C3—C4	57.03 (17)
C6—C5—C4—C9	178.34 (13)	C7—C2—C3—C4	−179.89 (13)
C6—C5—C4—C3	54.06 (17)	O4—C8—O2—C11	0.9 (2)
C2—N1—C6—C8	179.01 (13)	C6—C8—O2—C11	178.96 (15)
C2—N1—C6—C5	55.96 (17)	C3—C4—C9—O91	−56.50 (19)
O4—C8—C6—N1	−22.3 (2)	C5—C4—C9—O91	−179.57 (13)

D—H···A	D—H	H···A	D···A	D—H···A
O91—H91···N1i	0.82	2.07	2.883 (2)	171
N1—H1···O4ii	0.98 (2)	2.19 (2)	3.144 (2)	165 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O91—H91⋯N1i	0.82	2.07	2.883 (2)	171
N1—H1⋯O4ii	0.98 (2)	2.19 (2)	3.144 (2)	165 (2)

Symmetry codes: (i) ; (ii) .