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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 2| February 2013| Page o218
doi:10.1107/S1600536812051343

(7aR)-1-[(2R,5S,E)-6-Hy­dr­oxy-5,6-di­methyl­hept-3-en-2-yl]-7a-methyl­hexa­hydro-1H-inden-4(2H)-one

Marcos L. Rivadulla,a* Massene Sene,a María Gonzáleza and Berta Covelob

aDpto. Química Orgánica, Facultade de Química, Universidade de Vigo, E-36310 Vigo, Spain, and bUnidad de Difracción de Raios X de Monocristal, Servicio Determinación Estructural, Proteómica e Xenómica, CACTI-Universidade de Vigo, E-36310 Vigo, Spain
*Correspondence e-mail: m.lois@uvigo.es

(Received 13 December 2012; accepted 19 December 2012; online 12 January 2013)

The chiral title compound, C19H32O2, contains a [4.3.0]-bicyclic moiety in which the shared C—C bond presents a trans configuration and a side chain in which the C=C double bond shows an E conformation. The conformations of five- and six-membered rings are envelope (with the bridgehead atom bearing the methyl substituent as the flap) and chair, respectively, with a dihedral angle of 4.08 (17)° between the idealized planes of the rings. In the crystal, the mol­ecules are self-assembled via classical O—H⋯O hydrogen bonds, forming chains along [112]; these chains are linked by weak non-classical C—H⋯O hydrogen bonds, giving a two-dimensional supra­molecular structure parallel to (010). The absolute configuration was established according to the configuration of the starting material.

Related literature

The title compound is a precursor of the hormonally active form of vitamin D3. For general background to vitamin D3, see: Heaney (2008[Heaney, R. P. (2008). Clin. J. Am. Soc. Nephrol. 3, 1535-1541.]); Henry (2011[Henry, H. L. (2011). Best Pract. Res. Clin. Endocrinol. Metab. 25, 531-541.]). For related structures, see: Maehr & Uskokovic (2004[Maehr, H. & Uskokovic, M. R. (2004). Eur. J. Org. Chem. pp. 1703-1713.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data

  • C19H32O2

  • Mr = 292.45

  • Monoclinic, C 2

  • a = 20.057 (4) Å

  • b = 7.3816 (15) Å

  • c = 13.700 (3) Å

  • β = 112.324 (4)°

  • V = 1876.3 (6) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.07 mm−1

  • T = 293 K

  • 0.45 × 0.36 × 0.18 mm
Data collection

  • Bruker SMART 1000 CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.602, Tmax = 0.745

  • 4958 measured reflections

  • 3254 independent reflections

  • 2389 reflections with I > 2σ(I)

  • Rint = 0.018
Refinement

  • R[F2 > 2σ(F2)] = 0.048

  • wR(F2) = 0.152

  • S = 1.02

  • 3254 reflections

  • 196 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.14 e Å−3

  • Δρmin = −0.11 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O7′—H7′⋯O4i 0.82 2.08 2.876 (3) 164
C3A—H3A1⋯O7′ii 0.98 2.56 3.523 (3) 166
Symmetry codes: (i) [x+{\script{1\over 2}}, y+{\script{1\over 2}}, z+1]; (ii) -x+1, y, -z+2.

Data collection: SMART (Bruker, 1998[Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madinson, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1998[Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madinson, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812051343/pv2614sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812051343/pv2614Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812051343/pv2614Isup3.cml

checkCIF report


Comment top

The title compound is a precursor of 1α,25-dihydroxyvitamin D3 (calcitriol) analogue which is the hormonally active form of vitamin D3. Besides regulating calcium homeostasis, this form is also involved in other cellular processes such as cell differentiation; immune system regulation and gene transcription (Henry, 2011). Nevertheless, the clinical utility of this hormone for treatment of cancers and skin disorders is limited by its hypercalcemic effects (Heaney, 2008), for this purpose the design and synthesis of more selective biological-effect analogues is of paramount importance. In the title compound (Figure 1), the C3A—C7A shared bond of the bicyclic moiety presents a trans configuration. Besides, the 5-membered ring adopts an envelope conformation with puckering parameters Q = 0.462 (3) Å and ϕ = 136.5 (4)° and with the bridgehead C7A atom bearing the methyl substituent as the flap (Cremer & Pople, 1975) and the 6-membered ring presents a chair conformation with puckering parameters Q = 0.556 (3) Å, θ = 169.5 (3)° and ϕ = 133.4 (18)° (Cremer & Pople, 1975). The value for the dihedral angle between the idealized planes of the rings is 4.08 (17)°. All bond lengths and bond angles are normal comparable to those observed in similar crystal structures (Maehr & Uskokovic, 2004). In the crystal structure, the molecules are self-assembled via classical O—H···O hydrogen bonds to form a chain along [112], the resulting chains are connected by weak non-classical C—H···O hydrogen bonds to create a two-dimensional supramolecular structure (Table 1, Figure 2).

Related literature top

The title compound is a precursor of the hormonally active form of vitamin D3. For general background to vitamin D3, see: Heaney (2008); Henry (2011). For related structures, see: Maehr & Uskokovic (2004). For puckering parameters, see: Cremer & Pople (1975).

Experimental top

Over a stirring solution of inhoffen-lythgoe diol (2.1 g; 7.2 mmol) in CH2Cl2 (10 ml), PDC S-methyl-3-hydroxy-2-methylpropionate (5.4 g; 14.4 mmol) was added. The mixture was stirred at room temperature for 16 h then it was quenched with ethylic ether (20 ml) and stirred one more hour. The solid precipitated was filtered over celite, the organic layer was concentrated and the residue was purified by flash column chromatography on silica gel (10% ethyl acetate/hexane) to afford the title compound (1.8 g; 80%). The crystals were obtained by slow evaporation in a closed camera of a solution of the compound in a mixture of ethyl acetate/hexane (7:3).

Refinement top

All H-atoms were positioned and refined using a riding model with O–H = 0.82 Å and C–H = 0.98, 0.97, 0.96 and 0.93 Å for methine, methylelne, methyl and vinyl H-atoms, respectively. The H-atoms were allowed Uiso = 1.5Ueq(O/C-methyl) or 1.2Ueq(the rest of the C atoms). Due to insufficient anamolous dispersion effects, an absolute structure was not established in this analysis and 1457 Friedel pairs were not merged. However, the absolute configuration of the title compound was established according to the configuration of starting material.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound. Non-H atoms are present as displacement ellipsoids at the 30% probability level.
[Figure 2] Fig. 2. View of two-dimensional supramolecular organization in the crystal structure of the title compound. H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarify.
(7aR)-1-[(2R,5S,E)-6-Hydroxy-5,6-dimethylhept- 3-en-2-yl]-7a-methylhexahydro-1H-inden-4(2H)-one top
Crystal data top
C19H32O2F(000) = 648
Mr = 292.45Dx = 1.035 Mg m−3
Monoclinic, C2Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2yCell parameters from 1729 reflections
a = 20.057 (4) Åθ = 2.2–23.0°
b = 7.3816 (15) ŵ = 0.07 mm−1
c = 13.700 (3) ÅT = 293 K
β = 112.324 (4)°Prism, colourless
V = 1876.3 (6) Å30.45 × 0.36 × 0.18 mm
Z = 4
Data collection top
Bruker SMART 1000 CCD
diffractometer		3254 independent reflections
Radiation source: fine-focus sealed tube2389 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.018
ϕ and ω scansθmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −23→14
Tmin = 0.602, Tmax = 0.745k = −8→8
4958 measured reflectionsl = −13→16
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0934P)2 + 0.0697P]
where P = (Fo2 + 2Fc2)/3
3254 reflections(Δ/σ)max < 0.001
196 parametersΔρmax = 0.14 e Å−3
1 restraintΔρmin = −0.11 e Å−3
Crystal data top
C19H32O2V = 1876.3 (6) Å3
Mr = 292.45Z = 4
Monoclinic, C2Mo Kα radiation
a = 20.057 (4) ŵ = 0.07 mm−1
b = 7.3816 (15) ÅT = 293 K
c = 13.700 (3) Å0.45 × 0.36 × 0.18 mm
β = 112.324 (4)°
Data collection top
Bruker SMART 1000 CCD
diffractometer		3254 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2389 reflections with I > 2σ(I)
Tmin = 0.602, Tmax = 0.745Rint = 0.018
4958 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0481 restraint
wR(F2) = 0.152H-atom parameters constrained
S = 1.02Δρmax = 0.14 e Å−3
3254 reflectionsΔρmin = −0.11 e Å−3
196 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
xyzUiso*/Ueq
C10.31315 (12)−0.0108 (3)0.83385 (16)0.0467 (6)
H10.35240.03120.81350.056*
C20.32284 (17)−0.2166 (4)0.8512 (2)0.0663 (8)
H2A0.3046−0.25560.90390.080*
H2B0.3735−0.24840.87520.080*
C30.28017 (17)−0.3084 (4)0.7442 (2)0.0737 (8)
H3A0.3107−0.38960.72390.088*
H3B0.2394−0.37590.74690.088*
C3A0.25554 (14)−0.1495 (3)0.66904 (18)0.0554 (7)
H3A10.2968−0.11400.65160.066*
C40.19282 (15)−0.1736 (4)0.5661 (2)0.0619 (7)
O40.16051 (12)−0.3154 (3)0.53886 (15)0.0849 (7)
C50.17509 (18)−0.0054 (5)0.4997 (2)0.0807 (9)
H5A0.1294−0.02240.44110.097*
H5B0.21180.01390.47080.097*
C60.17031 (19)0.1620 (5)0.5617 (2)0.0827 (10)
H6A0.12530.15840.57270.099*
H6B0.16950.26900.52020.099*
C70.23275 (15)0.1787 (4)0.6691 (2)0.0673 (8)
H7A0.27690.20400.65820.081*
H7B0.22360.27980.70750.081*
C7A0.24264 (12)0.0069 (3)0.73468 (16)0.0472 (6)
C80.17703 (13)−0.0288 (5)0.7620 (2)0.0706 (8)
H8A0.1349−0.03860.69820.106*
H8B0.17100.06940.80380.106*
H8C0.1838−0.13970.80120.106*
C1'0.31086 (19)0.2943 (4)0.9234 (2)0.0799 (10)
H1'10.34170.34210.89050.120*
H1'20.32270.34960.99140.120*
H1'30.26150.32000.88010.120*
C2'0.32153 (14)0.0889 (4)0.93674 (19)0.0552 (7)
H2'0.28570.04050.96240.066*
C3'0.39471 (14)0.0496 (4)1.01717 (17)0.0554 (7)
H3'0.43310.08881.00040.067*
C4'0.41212 (13)−0.0327 (4)1.10809 (18)0.0578 (7)
H4'0.3744−0.07061.12680.069*
C5'0.48679 (13)−0.0715 (4)1.18480 (19)0.0564 (7)
H5'0.5196−0.03671.15030.068*
C6'0.4971 (2)−0.2739 (5)1.2070 (4)0.1075 (14)
H6'10.4895−0.33751.14250.161*
H6'20.4631−0.31561.23590.161*
H6'30.5452−0.29621.25660.161*
C7'0.50827 (14)0.0412 (5)1.2868 (2)0.0674 (8)
O7'0.58126 (10)−0.0077 (3)1.34707 (14)0.0824 (7)
H7'0.59590.04941.40260.124*
C8'0.5057 (2)0.2410 (5)1.2604 (3)0.1151 (17)
H8'10.54090.26731.23070.173*
H8'20.51590.31101.32350.173*
H8'30.45850.27151.21040.173*
C9'0.4620 (2)0.0049 (11)1.3478 (3)0.145 (2)
H9'10.47650.08221.40860.218*
H9'20.4672−0.11941.36990.218*
H9'30.41260.02871.30400.218*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0422 (12)0.0519 (14)0.0368 (10)−0.0019 (12)0.0048 (9)−0.0014 (11)
C20.0731 (18)0.0573 (17)0.0500 (13)0.0055 (14)0.0027 (13)−0.0010 (13)
C30.088 (2)0.0542 (16)0.0582 (15)0.0030 (15)0.0040 (14)−0.0063 (14)
C3A0.0536 (14)0.0559 (16)0.0444 (13)−0.0055 (12)0.0048 (11)−0.0064 (11)
C40.0613 (16)0.0701 (19)0.0438 (13)−0.0111 (15)0.0079 (12)−0.0117 (13)
O40.0868 (15)0.0816 (15)0.0583 (11)−0.0232 (13)−0.0039 (10)−0.0162 (11)
C50.086 (2)0.090 (2)0.0425 (13)−0.0127 (18)−0.0011 (13)0.0046 (16)
C60.093 (2)0.077 (2)0.0523 (16)0.0033 (18)−0.0011 (16)0.0166 (15)
C70.0736 (19)0.0615 (18)0.0467 (14)−0.0021 (16)0.0002 (13)0.0083 (13)
C7A0.0444 (13)0.0503 (14)0.0385 (10)−0.0030 (12)0.0061 (9)0.0007 (11)
C80.0474 (14)0.101 (2)0.0565 (14)−0.0084 (15)0.0117 (11)−0.0040 (16)
C1'0.095 (2)0.072 (2)0.0541 (15)0.0132 (17)0.0068 (15)−0.0143 (14)
C2'0.0507 (14)0.0651 (18)0.0419 (13)−0.0001 (12)0.0086 (11)−0.0079 (11)
C3'0.0508 (15)0.0722 (19)0.0359 (12)−0.0071 (12)0.0081 (11)−0.0076 (11)
C4'0.0484 (14)0.0715 (19)0.0470 (13)−0.0112 (13)0.0108 (11)−0.0020 (13)
C5'0.0483 (15)0.0643 (18)0.0478 (13)−0.0007 (12)0.0081 (11)−0.0007 (12)
C6'0.086 (3)0.066 (2)0.136 (3)0.0032 (18)0.003 (2)0.007 (2)
C7'0.0483 (15)0.096 (3)0.0433 (12)0.0113 (14)0.0012 (11)−0.0076 (13)
O7'0.0566 (12)0.1072 (18)0.0569 (10)0.0184 (12)−0.0083 (9)−0.0136 (12)
C8'0.097 (3)0.082 (3)0.112 (3)0.018 (2)−0.022 (2)−0.034 (2)
C9'0.094 (3)0.287 (7)0.0559 (17)0.032 (4)0.0299 (19)0.005 (3)
Geometric parameters (Å, º) top
C1—C21.538 (4)C8—H8C0.9600
C1—C2'1.541 (3)C1'—C2'1.533 (4)
C1—C7A1.550 (3)C1'—H1'10.9600
C1—H10.9800C1'—H1'20.9600
C2—C31.545 (4)C1'—H1'30.9600
C2—H2A0.9700C2'—C3'1.491 (4)
C2—H2B0.9700C2'—H2'0.9800
C3—C3A1.515 (4)C3'—C4'1.308 (3)
C3—H3A0.9700C3'—H3'0.9300
C3—H3B0.9700C4'—C5'1.495 (3)
C3A—C41.501 (3)C4'—H4'0.9300
C3A—C7A1.545 (3)C5'—C6'1.523 (5)
C3A—H3A10.9800C5'—C7'1.540 (4)
C4—O41.213 (3)C5'—H5'0.9800
C4—C51.500 (4)C6'—H6'10.9600
C5—C61.524 (5)C6'—H6'20.9600
C5—H5A0.9700C6'—H6'30.9600
C5—H5B0.9700C7'—O7'1.427 (3)
C6—C71.532 (4)C7'—C9'1.490 (5)
C6—H6A0.9700C7'—C8'1.515 (6)
C6—H6B0.9700O7'—H7'0.8200
C7—C7A1.524 (4)C8'—H8'10.9600
C7—H7A0.9700C8'—H8'20.9600
C7—H7B0.9700C8'—H8'30.9600
C7A—C81.522 (3)C9'—H9'10.9600
C8—H8A0.9600C9'—H9'20.9600
C8—H8B0.9600C9'—H9'30.9600
C2—C1—C2'111.5 (2)H8A—C8—H8B109.5
C2—C1—C7A103.77 (19)C7A—C8—H8C109.5
C2'—C1—C7A120.50 (19)H8A—C8—H8C109.5
C2—C1—H1106.8H8B—C8—H8C109.5
C2'—C1—H1106.8C2'—C1'—H1'1109.5
C7A—C1—H1106.8C2'—C1'—H1'2109.5
C1—C2—C3107.2 (2)H1'1—C1'—H1'2109.5
C1—C2—H2A110.3C2'—C1'—H1'3109.5
C3—C2—H2A110.3H1'1—C1'—H1'3109.5
C1—C2—H2B110.3H1'2—C1'—H1'3109.5
C3—C2—H2B110.3C3'—C2'—C1'109.5 (2)
H2A—C2—H2B108.5C3'—C2'—C1108.5 (2)
C3A—C3—C2103.0 (2)C1'—C2'—C1113.7 (2)
C3A—C3—H3A111.2C3'—C2'—H2'108.3
C2—C3—H3A111.2C1'—C2'—H2'108.3
C3A—C3—H3B111.2C1—C2'—H2'108.3
C2—C3—H3B111.2C4'—C3'—C2'128.7 (3)
H3A—C3—H3B109.1C4'—C3'—H3'115.6
C4—C3A—C3119.2 (2)C2'—C3'—H3'115.6
C4—C3A—C7A111.7 (2)C3'—C4'—C5'126.3 (2)
C3—C3A—C7A105.5 (2)C3'—C4'—H4'116.8
C4—C3A—H3A1106.6C5'—C4'—H4'116.8
C3—C3A—H3A1106.6C4'—C5'—C6'110.6 (2)
C7A—C3A—H3A1106.6C4'—C5'—C7'113.2 (2)
O4—C4—C5123.5 (2)C6'—C5'—C7'112.2 (3)
O4—C4—C3A123.4 (3)C4'—C5'—H5'106.8
C5—C4—C3A113.1 (2)C6'—C5'—H5'106.8
C4—C5—C6112.5 (2)C7'—C5'—H5'106.8
C4—C5—H5A109.1C5'—C6'—H6'1109.5
C6—C5—H5A109.1C5'—C6'—H6'2109.5
C4—C5—H5B109.1H6'1—C6'—H6'2109.5
C6—C5—H5B109.1C5'—C6'—H6'3109.5
H5A—C5—H5B107.8H6'1—C6'—H6'3109.5
C5—C6—C7113.5 (3)H6'2—C6'—H6'3109.5
C5—C6—H6A108.9O7'—C7'—C9'110.5 (3)
C7—C6—H6A108.9O7'—C7'—C8'108.6 (3)
C5—C6—H6B108.9C9'—C7'—C8'109.6 (4)
C7—C6—H6B108.9O7'—C7'—C5'105.1 (2)
H6A—C6—H6B107.7C9'—C7'—C5'113.1 (3)
C7A—C7—C6112.0 (2)C8'—C7'—C5'109.7 (3)
C7A—C7—H7A109.2C7'—O7'—H7'109.5
C6—C7—H7A109.2C7'—C8'—H8'1109.5
C7A—C7—H7B109.2C7'—C8'—H8'2109.5
C6—C7—H7B109.2H8'1—C8'—H8'2109.5
H7A—C7—H7B107.9C7'—C8'—H8'3109.5
C8—C7A—C7111.0 (2)H8'1—C8'—H8'3109.5
C8—C7A—C3A111.4 (2)H8'2—C8'—H8'3109.5
C7—C7A—C3A106.98 (19)C7'—C9'—H9'1109.5
C8—C7A—C1110.87 (18)C7'—C9'—H9'2109.5
C7—C7A—C1117.3 (2)H9'1—C9'—H9'2109.5
C3A—C7A—C198.54 (18)C7'—C9'—H9'3109.5
C7A—C8—H8A109.5H9'1—C9'—H9'3109.5
C7A—C8—H8B109.5H9'2—C9'—H9'3109.5
C2'—C1—C2—C3153.7 (2)C2—C1—C7A—C875.8 (3)
C7A—C1—C2—C322.6 (3)C2'—C1—C7A—C8−49.9 (3)
C1—C2—C3—C3A6.2 (3)C2—C1—C7A—C7−155.3 (2)
C2—C3—C3A—C4−159.6 (3)C2'—C1—C7A—C779.0 (3)
C2—C3—C3A—C7A−33.2 (3)C2—C1—C7A—C3A−41.2 (2)
C3—C3A—C4—O4−0.6 (5)C2'—C1—C7A—C3A−166.8 (2)
C7A—C3A—C4—O4−124.0 (3)C2—C1—C2'—C3'59.0 (3)
C3—C3A—C4—C5−179.5 (3)C7A—C1—C2'—C3'−179.0 (2)
C7A—C3A—C4—C557.1 (3)C2—C1—C2'—C1'−178.8 (3)
O4—C4—C5—C6132.6 (3)C7A—C1—C2'—C1'−56.9 (3)
C3A—C4—C5—C6−48.5 (4)C1'—C2'—C3'—C4'117.4 (3)
C4—C5—C6—C746.1 (4)C1—C2'—C3'—C4'−118.0 (3)
C5—C6—C7—C7A−52.5 (4)C2'—C3'—C4'—C5'178.7 (3)
C6—C7—C7A—C8−63.9 (3)C3'—C4'—C5'—C6'−122.4 (4)
C6—C7—C7A—C3A57.8 (3)C3'—C4'—C5'—C7'110.6 (3)
C6—C7—C7A—C1167.2 (2)C4'—C5'—C7'—O7'−177.4 (2)
C4—C3A—C7A—C861.0 (3)C6'—C5'—C7'—O7'56.5 (3)
C3—C3A—C7A—C8−69.8 (3)C4'—C5'—C7'—C9'62.0 (4)
C4—C3A—C7A—C7−60.5 (3)C6'—C5'—C7'—C9'−64.2 (4)
C3—C3A—C7A—C7168.7 (2)C4'—C5'—C7'—C8'−60.8 (3)
C4—C3A—C7A—C1177.5 (2)C6'—C5'—C7'—C8'173.1 (3)
C3—C3A—C7A—C146.7 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O7′—H7′···O4i0.822.082.876 (3)164
C3A—H3A1···O7′ii0.982.563.523 (3)166
Symmetry codes: (i) x+1/2, y+1/2, z+1; (ii) −x+1, y, −z+2.

Experimental details

Crystal data
Chemical formulaC19H32O2
Mr292.45
Crystal system, space groupMonoclinic, C2
Temperature (K)293
a, b, c (Å)20.057 (4), 7.3816 (15), 13.700 (3)
β (°) 112.324 (4)
V (Å3)1876.3 (6)
Z4
Radiation typeMo Kα
µ (mm−1)0.07
Crystal size (mm)0.45 × 0.36 × 0.18
Data collection
DiffractometerBruker SMART 1000 CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.602, 0.745
No. of measured, independent and
observed [I > 2σ(I)] reflections		4958, 3254, 2389
Rint0.018
(sin θ/λ)max (Å−1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.152, 1.02
No. of reflections3254
No. of parameters196
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.14, −0.11

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and Mercury (Macrae et al., 2006), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O7'—H7'···O4i0.822.082.876 (3)163.9
C3A—H3A1···O7'ii0.982.563.523 (3)166.4
Symmetry codes: (i) x+1/2, y+1/2, z+1; (ii) −x+1, y, −z+2.
 

Acknowledgements

This work was supported financially by the Spanish Ministry of Foreign Affairs and Cooperation (PCIA/030052/10) and the Xunta de Galicia (INCITE845B, INCITE08PXIB314255PR).

References

First citationBruker (1998). SMART and SAINT. Bruker AXS Inc., Madinson, Wisconsin, USA.  Google Scholar
 First citationCremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.  CrossRef CAS Web of Science Google Scholar
 First citationHeaney, R. P. (2008). Clin. J. Am. Soc. Nephrol. 3, 1535–1541.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationHenry, H. L. (2011). Best Pract. Res. Clin. Endocrinol. Metab. 25, 531–541.  Web of Science CrossRef CAS PubMed Google Scholar
 First citationMacrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationMaehr, H. & Uskokovic, M. R. (2004). Eur. J. Org. Chem. pp. 1703–1713.  Web of Science CSD CrossRef Google Scholar
 First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2056-9890
Volume 69| Part 2| February 2013| Page o218
doi:10.1107/S1600536812051343
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