rac-(1S*,4aS*,8aS*)-4a-Hy-droxy-2-methyl-perhydro-spiro-[isoquinoline-4,1'-cyclo-hexa-n]-2'-one.

In the title compound, C15H25NO2, all three six-membered rings adopt chair conformations. The cyclo-hexane and piperidine rings within the perhydro-isoquinoline are trans-trans fused. The N atom has a trigonal-pyramidal geometry (the sum of the bond angles is 328.0°). The methyl substituent occupies the sterically preferrable equatorial position. In the crystal, mol-ecules form infinite [100] chains via O-H⋯N hydrogen bonds.

Related literature

For general background to the synthesis, chemical properties and applications in medicine of the title compound, see: Plati & Wenner (1949 ▶); Ellefson et al. (1978 ▶); Soldatenkov et al. (2009 ▶). For related compounds, see: Plati & Wenner (1950 ▶); Soldatenkov et al. (2008 ▶); Soldatova et al. (2010 ▶); Siaka et al. (2012 ▶).

Experimental

Crystal data

C15H25NO2

M = 251.36

Monoclinic,

a = 5.8438 (2) Å

b = 18.5756 (7) Å

c = 12.2148 (5) Å

β = 95.116 (1)°

V = 1320.66 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 100 K

0.30 × 0.30 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.976, T max = 0.984

17142 measured reflections

3852 independent reflections

3221 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.102

S = 1.00

3852 reflections

167 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.48 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813007010/rk2397sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813007010/rk2397Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813007010/rk2397Isup3.cml

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

C15H25NO2	F(000) = 552
Mr = 251.36	Dx = 1.264 Mg m−3
Monoclinic, P21/n	Melting point = 437–439 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 5.8438 (2) Å	Cell parameters from 6340 reflections
b = 18.5756 (7) Å	θ = 2.2–32.6°
c = 12.2148 (5) Å	µ = 0.08 mm−1
β = 95.116 (1)°	T = 100 K
V = 1320.66 (9) Å3	Prism, colourless
Z = 4	0.30 × 0.30 × 0.20 mm

Bruker APEXII CCD diffractometer	3852 independent reflections
Radiation source: fine–focus sealed tube	3221 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
φ and ω scans	θmax = 30.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −8→8
Tmin = 0.976, Tmax = 0.984	k = −26→26
17142 measured reflections	l = −17→17

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)] = 0.037	Hydrogen site location: calc
wR(F2) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.055P)2 + 0.4P] where P = (Fo2 + 2Fc2)/3
3852 reflections	(Δ/σ)max < 0.001
167 parameters	Δρmax = 0.48 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	0.72882 (11)	0.10966 (4)	0.39294 (6)	0.01342 (14)
H1	0.847 (2)	0.1345 (7)	0.3939 (11)	0.020*
C1	0.47868 (14)	0.21494 (5)	0.37839 (7)	0.00990 (16)
C2	0.38858 (15)	0.19624 (5)	0.49006 (7)	0.01161 (17)
H2A	0.5143	0.1741	0.5384	0.014*
H2B	0.3421	0.2412	0.5257	0.014*
N3	0.19197 (13)	0.14659 (4)	0.47886 (6)	0.01124 (15)
C4	0.26546 (15)	0.07765 (5)	0.43377 (7)	0.01177 (17)
H4A	0.1356	0.0432	0.4293	0.014*
H4B	0.3919	0.0570	0.4834	0.014*
C4A	0.34662 (15)	0.08849 (5)	0.31979 (7)	0.01051 (16)
H4C	0.2157	0.1089	0.2712	0.013*
C5	0.41334 (16)	0.01620 (5)	0.27117 (7)	0.01355 (18)
H5A	0.5389	−0.0059	0.3197	0.016*
H5B	0.2797	−0.0168	0.2678	0.016*
C6	0.49189 (17)	0.02548 (5)	0.15586 (8)	0.01609 (18)
H6A	0.3619	0.0430	0.1053	0.019*
H6B	0.5416	−0.0216	0.1283	0.019*
C7	0.69080 (17)	0.07913 (5)	0.15765 (8)	0.01640 (19)
H7A	0.7326	0.0867	0.0817	0.020*
H7B	0.8264	0.0588	0.2014	0.020*
C8	0.62793 (16)	0.15179 (5)	0.20703 (7)	0.01312 (17)
H8A	0.5039	0.1747	0.1586	0.016*
H8B	0.7634	0.1840	0.2108	0.016*
C8A	0.54791 (15)	0.14266 (5)	0.32298 (7)	0.01031 (16)
C9	0.11013 (17)	0.13529 (5)	0.58766 (7)	0.01506 (18)
H9A	0.0565	0.1811	0.6158	0.023*
H9B	0.2360	0.1166	0.6381	0.023*
H9C	−0.0167	0.1006	0.5818	0.023*
O1'	0.18262 (12)	0.23557 (4)	0.22802 (6)	0.01587 (15)
C1'	0.29057 (15)	0.25807 (5)	0.31084 (7)	0.01110 (17)
C3'	0.69183 (15)	0.26497 (5)	0.40043 (8)	0.01269 (17)
H3A	0.8080	0.2399	0.4507	0.015*
H3B	0.7602	0.2732	0.3302	0.015*
C4'	0.63912 (16)	0.33810 (5)	0.45054 (8)	0.01341 (18)
H4D	0.5814	0.3308	0.5235	0.016*
H4E	0.7818	0.3670	0.4609	0.016*
C5'	0.45977 (16)	0.37870 (5)	0.37603 (8)	0.01372 (18)
H5C	0.5237	0.3905	0.3058	0.016*
H5D	0.4210	0.4244	0.4117	0.016*
C6'	0.24123 (16)	0.33311 (5)	0.35295 (8)	0.01422 (18)
H6C	0.1635	0.3288	0.4214	0.017*
H6D	0.1351	0.3581	0.2978	0.017*

	U11	U22	U33	U12	U13	U23
O1	0.0096 (3)	0.0127 (3)	0.0174 (3)	0.0011 (2)	−0.0015 (2)	0.0010 (2)
C1	0.0095 (4)	0.0095 (4)	0.0106 (4)	0.0001 (3)	0.0002 (3)	−0.0001 (3)
C2	0.0127 (4)	0.0115 (4)	0.0106 (4)	−0.0004 (3)	0.0008 (3)	−0.0006 (3)
N3	0.0123 (3)	0.0107 (3)	0.0110 (3)	−0.0001 (3)	0.0026 (3)	0.0001 (3)
C4	0.0127 (4)	0.0104 (4)	0.0124 (4)	0.0005 (3)	0.0019 (3)	0.0009 (3)
C4A	0.0109 (4)	0.0095 (4)	0.0111 (4)	−0.0003 (3)	0.0007 (3)	−0.0004 (3)
C5	0.0169 (4)	0.0101 (4)	0.0138 (4)	−0.0005 (3)	0.0022 (3)	−0.0010 (3)
C6	0.0218 (5)	0.0125 (4)	0.0144 (4)	−0.0008 (3)	0.0042 (3)	−0.0031 (3)
C7	0.0189 (4)	0.0149 (4)	0.0164 (4)	−0.0001 (3)	0.0071 (3)	−0.0024 (3)
C8	0.0148 (4)	0.0120 (4)	0.0129 (4)	−0.0012 (3)	0.0036 (3)	−0.0005 (3)
C8A	0.0101 (4)	0.0099 (4)	0.0108 (4)	0.0006 (3)	0.0003 (3)	0.0004 (3)
C9	0.0172 (4)	0.0168 (4)	0.0117 (4)	0.0010 (3)	0.0040 (3)	0.0019 (3)
O1'	0.0163 (3)	0.0156 (3)	0.0149 (3)	0.0008 (2)	−0.0029 (2)	−0.0001 (2)
C1'	0.0104 (4)	0.0107 (4)	0.0124 (4)	−0.0004 (3)	0.0022 (3)	0.0019 (3)
C3'	0.0107 (4)	0.0111 (4)	0.0161 (4)	−0.0007 (3)	0.0001 (3)	−0.0015 (3)
C4'	0.0134 (4)	0.0114 (4)	0.0153 (4)	−0.0015 (3)	0.0005 (3)	−0.0016 (3)
C5'	0.0157 (4)	0.0106 (4)	0.0149 (4)	0.0000 (3)	0.0019 (3)	−0.0004 (3)
C6'	0.0128 (4)	0.0120 (4)	0.0176 (4)	0.0023 (3)	0.0000 (3)	−0.0012 (3)

O1—C8A	1.4362 (10)	C7—C8	1.5363 (13)
O1—H1	0.829 (14)	C7—H7A	0.9900
C1—C1'	1.5393 (12)	C7—H7B	0.9900
C1—C2	1.5449 (12)	C8—C8A	1.5400 (12)
C1—C3'	1.5581 (12)	C8—H8A	0.9900
C1—C8A	1.5726 (12)	C8—H8B	0.9900
C2—N3	1.4701 (11)	C9—H9A	0.9800
C2—H2A	0.9900	C9—H9B	0.9800
C2—H2B	0.9900	C9—H9C	0.9800
N3—C9	1.4671 (11)	O1'—C1'	1.2175 (11)
N3—C4	1.4730 (11)	C1'—C6'	1.5223 (12)
C4—C4A	1.5237 (12)	C3'—C4'	1.5326 (12)
C4—H4A	0.9900	C3'—H3A	0.9900
C4—H4B	0.9900	C3'—H3B	0.9900
C4A—C5	1.5328 (12)	C4'—C5'	1.5250 (13)
C4A—C8A	1.5458 (12)	C4'—H4D	0.9900
C4A—H4C	1.0000	C4'—H4E	0.9900
C5—C6	1.5296 (13)	C5'—C6'	1.5373 (13)
C5—H5A	0.9900	C5'—H5C	0.9900
C5—H5B	0.9900	C5'—H5D	0.9900
C6—C7	1.5297 (13)	C6'—H6C	0.9900
C6—H6A	0.9900	C6'—H6D	0.9900
C6—H6B	0.9900
C8A—O1—H1	109.8 (9)	C7—C8—C8A	111.54 (7)
C1'—C1—C2	107.88 (7)	C7—C8—H8A	109.3
C1'—C1—C3'	107.69 (7)	C8A—C8—H8A	109.3
C2—C1—C3'	108.16 (7)	C7—C8—H8B	109.3
C1'—C1—C8A	114.36 (7)	C8A—C8—H8B	109.3
C2—C1—C8A	108.00 (7)	H8A—C8—H8B	108.0
C3'—C1—C8A	110.56 (7)	O1—C8A—C8	109.05 (7)
N3—C2—C1	112.58 (7)	O1—C8A—C4A	104.79 (7)
N3—C2—H2A	109.1	C8—C8A—C4A	109.95 (7)
C1—C2—H2A	109.1	O1—C8A—C1	108.20 (7)
N3—C2—H2B	109.1	C8—C8A—C1	114.37 (7)
C1—C2—H2B	109.1	C4A—C8A—C1	110.01 (7)
H2A—C2—H2B	107.8	N3—C9—H9A	109.5
C9—N3—C2	108.70 (7)	N3—C9—H9B	109.5
C9—N3—C4	110.10 (7)	H9A—C9—H9B	109.5
C2—N3—C4	109.19 (7)	N3—C9—H9C	109.5
N3—C4—C4A	110.58 (7)	H9A—C9—H9C	109.5
N3—C4—H4A	109.5	H9B—C9—H9C	109.5
C4A—C4—H4A	109.5	O1'—C1'—C6'	119.70 (8)
N3—C4—H4B	109.5	O1'—C1'—C1	123.99 (8)
C4A—C4—H4B	109.5	C6'—C1'—C1	116.31 (7)
H4A—C4—H4B	108.1	C4'—C3'—C1	114.31 (7)
C4—C4A—C5	110.42 (7)	C4'—C3'—H3A	108.7
C4—C4A—C8A	111.17 (7)	C1—C3'—H3A	108.7
C5—C4A—C8A	111.15 (7)	C4'—C3'—H3B	108.7
C4—C4A—H4C	108.0	C1—C3'—H3B	108.7
C5—C4A—H4C	108.0	H3A—C3'—H3B	107.6
C8A—C4A—H4C	108.0	C5'—C4'—C3'	110.61 (7)
C6—C5—C4A	111.44 (7)	C5'—C4'—H4D	109.5
C6—C5—H5A	109.3	C3'—C4'—H4D	109.5
C4A—C5—H5A	109.3	C5'—C4'—H4E	109.5
C6—C5—H5B	109.3	C3'—C4'—H4E	109.5
C4A—C5—H5B	109.3	H4D—C4'—H4E	108.1
H5A—C5—H5B	108.0	C4'—C5'—C6'	110.64 (7)
C5—C6—C7	110.51 (8)	C4'—C5'—H5C	109.5
C5—C6—H6A	109.5	C6'—C5'—H5C	109.5
C7—C6—H6A	109.5	C4'—C5'—H5D	109.5
C5—C6—H6B	109.5	C6'—C5'—H5D	109.5
C7—C6—H6B	109.5	H5C—C5'—H5D	108.1
H6A—C6—H6B	108.1	C1'—C6'—C5'	112.77 (7)
C6—C7—C8	111.71 (8)	C1'—C6'—H6C	109.0
C6—C7—H7A	109.3	C5'—C6'—H6C	109.0
C8—C7—H7A	109.3	C1'—C6'—H6D	109.0
C6—C7—H7B	109.3	C5'—C6'—H6D	109.0
C8—C7—H7B	109.3	H6C—C6'—H6D	107.8
H7A—C7—H7B	107.9
C1'—C1—C2—N3	66.10 (9)	C1'—C1—C8A—O1	178.11 (7)
C3'—C1—C2—N3	−177.68 (7)	C2—C1—C8A—O1	−61.79 (8)
C8A—C1—C2—N3	−58.00 (9)	C3'—C1—C8A—O1	56.37 (9)
C1—C2—N3—C9	−176.76 (7)	C1'—C1—C8A—C8	56.36 (10)
C1—C2—N3—C4	63.10 (9)	C2—C1—C8A—C8	176.46 (7)
C9—N3—C4—C4A	178.93 (7)	C3'—C1—C8A—C8	−65.38 (9)
C2—N3—C4—C4A	−61.80 (9)	C1'—C1—C8A—C4A	−67.95 (9)
N3—C4—C4A—C5	−177.62 (7)	C2—C1—C8A—C4A	52.15 (9)
N3—C4—C4A—C8A	58.53 (9)	C3'—C1—C8A—C4A	170.31 (7)
C4—C4A—C5—C6	179.09 (7)	C2—C1—C1'—O1'	−111.77 (9)
C8A—C4A—C5—C6	−57.05 (10)	C3'—C1—C1'—O1'	131.70 (9)
C4A—C5—C6—C7	56.19 (10)	C8A—C1—C1'—O1'	8.39 (12)
C5—C6—C7—C8	−55.41 (11)	C2—C1—C1'—C6'	68.10 (9)
C6—C7—C8—C8A	55.69 (10)	C3'—C1—C1'—C6'	−48.43 (10)
C7—C8—C8A—O1	59.18 (9)	C8A—C1—C1'—C6'	−171.74 (7)
C7—C8—C8A—C4A	−55.19 (9)	C1'—C1—C3'—C4'	52.23 (10)
C7—C8—C8A—C1	−179.54 (7)	C2—C1—C3'—C4'	−64.11 (9)
C4—C4A—C8A—O1	62.26 (9)	C8A—C1—C3'—C4'	177.83 (7)
C5—C4A—C8A—O1	−61.17 (9)	C1—C3'—C4'—C5'	−58.21 (10)
C4—C4A—C8A—C8	179.33 (7)	C3'—C4'—C5'—C6'	55.80 (10)
C5—C4A—C8A—C8	55.90 (9)	O1'—C1'—C6'—C5'	−129.56 (9)
C4—C4A—C8A—C1	−53.84 (9)	C1—C1'—C6'—C5'	50.56 (10)
C5—C4A—C8A—C1	−177.27 (7)	C4'—C5'—C6'—C1'	−52.24 (10)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N3i	0.830 (12)	2.195 (12)	2.8967 (10)	142.3 (12)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N3i	0.830 (12)	2.195 (12)	2.8967 (10)	142.3 (12)

Symmetry code: (i) .