(1R,3S,8R)-3,7,7,10-Tetra-methyl-tri-cyclo-[6.4.0.0(1,3)]dodec-9-en-11-one.

The absolute configuration of the title compound, C16H24O, has been deduced from the chemical pathway. The six-membered ring has a roughly half-chair conformation with the quaternary C atom as the flap. The seven-membered ring displays a chair conformation. In the crystal, there is a weak C-H⋯O hydrogen bond between the methyl-ene group of the cyclo-propane ring and the carbonyl group of a screw-axis-related mol-ecule, which builds up a zigzag-like chain along the b-axis direction.

Related literature

For related structures, see: Benharref et al. (2012 ▶); Gassman & Gorman (1990 ▶); Lassaba et al. (1997 ▶). For ring puckering analysis, see: Cremer & Pople (1975 ▶). For structural discussion, see: Evans & Boeyens (1989 ▶); Spek (2009 ▶). For chemical properties, see: Auhmani et al. (2002 ▶); Danyang et al. (2007 ▶); Tetsuhiro et al. (2003 ▶).

Experimental

Crystal data

C16H24O

M = 232.35

Monoclinic,

a = 6.4379 (2) Å

b = 7.8889 (3) Å

c = 13.5122 (5) Å

β = 97.430 (2)°

V = 680.49 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.07 mm−1

T = 180 K

0.38 × 0.23 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008a ▶) T min = 0.661, T max = 0.747

15568 measured reflections

4902 independent reflections

4331 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.111

S = 1.04

4902 reflections

158 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2012 ▶); cell refinement: SAINT (Bruker, 2012 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008b ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶), ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL2013.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813034041/fy2107sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813034041/fy2107Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536813034041/fy2107Isup3.cml

Additional supporting information: crystallographic information; 3D view; checkCIF report

C16H24O	F(000) = 256
Mr = 232.35	Dx = 1.134 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 7217 reflections
a = 6.4379 (2) Å	θ = 3.0–33.0°
b = 7.8889 (3) Å	µ = 0.07 mm−1
c = 13.5122 (5) Å	T = 180 K
β = 97.430 (2)°	Plate, colourless
V = 680.49 (4) Å3	0.38 × 0.23 × 0.08 mm
Z = 2

Bruker APEXII CCD diffractometer	4902 independent reflections
Radiation source: sealed tube	4331 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
φ and ω scans	θmax = 33.2°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)	h = −9→9
Tmin = 0.661, Tmax = 0.747	k = −12→12
15568 measured reflections	l = −20→20

Refinement on F2	1 restraint
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041	H-atom parameters constrained
wR(F2) = 0.111	w = 1/[σ2(Fo2) + (0.0667P)2 + 0.0218P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
4902 reflections	Δρmax = 0.30 e Å−3
158 parameters	Δρmin = −0.18 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.31651 (18)	0.79421 (18)	0.28074 (9)	0.0192 (2)
C2	0.2552 (2)	0.98024 (19)	0.27484 (11)	0.0255 (3)
H2A	0.1104	1.0088	0.2457	0.031*
H2B	0.3159	1.0555	0.3297	0.031*
C3	0.40116 (18)	0.91018 (18)	0.20572 (9)	0.0213 (3)
C4	0.3155 (2)	0.8894 (2)	0.09629 (10)	0.0261 (3)
H4A	0.3706	0.9821	0.0577	0.031*
H4B	0.1611	0.9005	0.0888	0.031*
C5	0.3716 (2)	0.7200 (2)	0.05222 (11)	0.0318 (3)
H5A	0.5148	0.6876	0.0819	0.038*
H5B	0.3727	0.7338	−0.0205	0.038*
C6	0.2204 (3)	0.5769 (2)	0.07006 (11)	0.0322 (3)
H6A	0.2565	0.4778	0.0308	0.039*
H6B	0.0780	0.6135	0.0417	0.039*
C7	0.2086 (2)	0.51533 (19)	0.17792 (10)	0.0244 (3)
C8	0.14660 (17)	0.66525 (17)	0.24508 (9)	0.0191 (2)
H8	0.0359	0.7304	0.2023	0.023*
C9	0.04465 (19)	0.60496 (19)	0.33343 (10)	0.0236 (3)
H9	−0.0870	0.5499	0.3191	0.028*
C10	0.1211 (2)	0.6213 (2)	0.42964 (11)	0.0263 (3)
C11	0.3324 (2)	0.6937 (2)	0.45837 (10)	0.0271 (3)
C12	0.4560 (2)	0.7448 (2)	0.37599 (10)	0.0263 (3)
H12A	0.5471	0.6493	0.3614	0.032*
H12B	0.5474	0.8418	0.3988	0.032*
C13	0.6305 (2)	0.9621 (2)	0.22205 (12)	0.0310 (3)
H13A	0.6697	0.9941	0.2921	0.047*
H13B	0.6521	1.0589	0.1791	0.047*
H13C	0.7175	0.8669	0.2056	0.047*
C14	0.4145 (2)	0.4307 (2)	0.22037 (13)	0.0352 (4)
H14A	0.4383	0.3308	0.1802	0.053*
H14B	0.4072	0.3960	0.2895	0.053*
H14C	0.5301	0.5110	0.2186	0.053*
C15	0.0350 (3)	0.3801 (2)	0.16921 (14)	0.0372 (4)
H15A	0.0327	0.3251	0.2341	0.056*
H15B	0.0626	0.2950	0.1197	0.056*
H15C	−0.1007	0.4339	0.1483	0.056*
C16	0.0016 (3)	0.5678 (3)	0.51319 (14)	0.0403 (4)
H16A	−0.1322	0.5173	0.4852	0.060*
H16B	−0.0246	0.6670	0.5534	0.060*
H16C	0.0839	0.4843	0.5553	0.060*
O1	0.4059 (2)	0.7093 (2)	0.54568 (8)	0.0492 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0190 (4)	0.0222 (6)	0.0168 (5)	−0.0001 (4)	0.0033 (4)	0.0009 (4)
C2	0.0287 (6)	0.0230 (7)	0.0263 (6)	0.0003 (5)	0.0095 (5)	−0.0021 (5)
C3	0.0214 (5)	0.0230 (7)	0.0202 (6)	0.0001 (4)	0.0055 (4)	0.0023 (5)
C4	0.0300 (6)	0.0289 (7)	0.0199 (6)	0.0033 (5)	0.0047 (4)	0.0061 (5)
C5	0.0407 (7)	0.0376 (9)	0.0189 (6)	0.0035 (6)	0.0100 (5)	−0.0003 (6)
C6	0.0446 (7)	0.0312 (8)	0.0208 (7)	0.0009 (6)	0.0043 (5)	−0.0060 (6)
C7	0.0277 (5)	0.0225 (7)	0.0227 (6)	0.0030 (5)	0.0019 (4)	−0.0019 (5)
C8	0.0175 (4)	0.0214 (6)	0.0181 (5)	0.0022 (4)	0.0015 (4)	0.0013 (5)
C9	0.0205 (5)	0.0246 (7)	0.0263 (6)	0.0004 (5)	0.0057 (4)	0.0040 (5)
C10	0.0284 (6)	0.0277 (7)	0.0242 (6)	0.0020 (5)	0.0082 (5)	0.0070 (5)
C11	0.0308 (6)	0.0311 (8)	0.0190 (6)	0.0015 (5)	0.0019 (4)	0.0064 (5)
C12	0.0225 (5)	0.0371 (8)	0.0185 (6)	−0.0035 (5)	0.0000 (4)	0.0033 (5)
C13	0.0240 (5)	0.0370 (9)	0.0326 (7)	−0.0047 (5)	0.0061 (5)	0.0056 (6)
C14	0.0369 (7)	0.0299 (8)	0.0390 (8)	0.0146 (6)	0.0056 (6)	−0.0002 (6)
C15	0.0438 (8)	0.0276 (8)	0.0393 (8)	−0.0068 (6)	0.0020 (6)	−0.0064 (7)
C16	0.0423 (7)	0.0500 (11)	0.0312 (8)	−0.0022 (7)	0.0150 (6)	0.0136 (7)
O1	0.0509 (6)	0.0765 (11)	0.0185 (5)	−0.0110 (7)	−0.0021 (4)	0.0070 (6)

C1—C3	1.5181 (18)	C8—H8	1.0000
C1—C2	1.519 (2)	C9—C10	1.336 (2)
C1—C12	1.5220 (18)	C9—H9	0.9500
C1—C8	1.5255 (18)	C10—C11	1.4796 (19)
C2—C3	1.5123 (17)	C10—C16	1.5065 (19)
C2—H2A	0.9900	C11—O1	1.2192 (17)
C2—H2B	0.9900	C11—C12	1.5048 (18)
C3—C4	1.5186 (19)	C12—H12A	0.9900
C3—C13	1.5207 (17)	C12—H12B	0.9900
C4—C5	1.525 (2)	C13—H13A	0.9800
C4—H4A	0.9900	C13—H13B	0.9800
C4—H4B	0.9900	C13—H13C	0.9800
C5—C6	1.530 (2)	C14—H14A	0.9800
C5—H5A	0.9900	C14—H14B	0.9800
C5—H5B	0.9900	C14—H14C	0.9800
C6—C7	1.548 (2)	C15—H15A	0.9800
C6—H6A	0.9900	C15—H15B	0.9800
C6—H6B	0.9900	C15—H15C	0.9800
C7—C14	1.528 (2)	C16—H16A	0.9800
C7—C15	1.538 (2)	C16—H16B	0.9800
C7—C8	1.5733 (18)	C16—H16C	0.9800
C8—C9	1.5115 (17)
C3—C1—C2	59.73 (9)	C1—C8—C7	117.29 (9)
C3—C1—C12	119.71 (10)	C9—C8—H8	105.6
C2—C1—C12	114.38 (12)	C1—C8—H8	105.6
C3—C1—C8	119.72 (11)	C7—C8—H8	105.6
C2—C1—C8	117.19 (10)	C10—C9—C8	126.53 (12)
C12—C1—C8	114.63 (11)	C10—C9—H9	116.7
C3—C2—C1	60.10 (9)	C8—C9—H9	116.7
C3—C2—H2A	117.8	C9—C10—C11	120.23 (11)
C1—C2—H2A	117.8	C9—C10—C16	122.86 (13)
C3—C2—H2B	117.8	C11—C10—C16	116.91 (14)
C1—C2—H2B	117.8	O1—C11—C10	121.43 (13)
H2A—C2—H2B	114.9	O1—C11—C12	120.82 (13)
C2—C3—C1	60.17 (9)	C10—C11—C12	117.73 (12)
C2—C3—C4	117.69 (11)	C11—C12—C1	112.55 (10)
C1—C3—C4	117.95 (11)	C11—C12—H12A	109.1
C2—C3—C13	118.74 (12)	C1—C12—H12A	109.1
C1—C3—C13	119.42 (11)	C11—C12—H12B	109.1
C4—C3—C13	113.19 (11)	C1—C12—H12B	109.1
C3—C4—C5	113.60 (12)	H12A—C12—H12B	107.8
C3—C4—H4A	108.8	C3—C13—H13A	109.5
C5—C4—H4A	108.8	C3—C13—H13B	109.5
C3—C4—H4B	108.8	H13A—C13—H13B	109.5
C5—C4—H4B	108.8	C3—C13—H13C	109.5
H4A—C4—H4B	107.7	H13A—C13—H13C	109.5
C4—C5—C6	113.40 (11)	H13B—C13—H13C	109.5
C4—C5—H5A	108.9	C7—C14—H14A	109.5
C6—C5—H5A	108.9	C7—C14—H14B	109.5
C4—C5—H5B	108.9	H14A—C14—H14B	109.5
C6—C5—H5B	108.9	C7—C14—H14C	109.5
H5A—C5—H5B	107.7	H14A—C14—H14C	109.5
C5—C6—C7	119.33 (13)	H14B—C14—H14C	109.5
C5—C6—H6A	107.5	C7—C15—H15A	109.5
C7—C6—H6A	107.5	C7—C15—H15B	109.5
C5—C6—H6B	107.5	H15A—C15—H15B	109.5
C7—C6—H6B	107.5	C7—C15—H15C	109.5
H6A—C6—H6B	107.0	H15A—C15—H15C	109.5
C14—C7—C15	108.17 (13)	H15B—C15—H15C	109.5
C14—C7—C6	110.16 (12)	C10—C16—H16A	109.5
C15—C7—C6	105.63 (12)	C10—C16—H16B	109.5
C14—C7—C8	112.60 (11)	H16A—C16—H16B	109.5
C15—C7—C8	109.25 (11)	C10—C16—H16C	109.5
C6—C7—C8	110.74 (12)	H16A—C16—H16C	109.5
C9—C8—C1	109.11 (10)	H16B—C16—H16C	109.5
C9—C8—C7	112.79 (12)
C12—C1—C2—C3	111.44 (11)	C3—C1—C8—C7	67.20 (16)
C8—C1—C2—C3	−110.21 (12)	C2—C1—C8—C7	136.14 (12)
C1—C2—C3—C4	108.01 (14)	C12—C1—C8—C7	−85.61 (13)
C1—C2—C3—C13	−109.34 (14)	C14—C7—C8—C9	−80.64 (14)
C12—C1—C3—C2	−102.54 (14)	C15—C7—C8—C9	39.58 (15)
C8—C1—C3—C2	106.03 (12)	C6—C7—C8—C9	155.52 (11)
C2—C1—C3—C4	−107.58 (13)	C14—C7—C8—C1	47.41 (16)
C12—C1—C3—C4	149.87 (13)	C15—C7—C8—C1	167.63 (12)
C8—C1—C3—C4	−1.55 (17)	C6—C7—C8—C1	−76.43 (14)
C2—C1—C3—C13	108.24 (15)	C1—C8—C9—C10	−17.09 (19)
C12—C1—C3—C13	5.7 (2)	C7—C8—C9—C10	115.13 (15)
C8—C1—C3—C13	−145.73 (13)	C8—C9—C10—C11	−4.7 (2)
C2—C3—C4—C5	−134.89 (13)	C8—C9—C10—C16	175.72 (16)
C1—C3—C4—C5	−65.84 (15)	C9—C10—C11—O1	−179.74 (16)
C13—C3—C4—C5	80.48 (16)	C16—C10—C11—O1	−0.1 (2)
C3—C4—C5—C6	84.92 (16)	C9—C10—C11—C12	−0.8 (2)
C4—C5—C6—C7	−65.63 (18)	C16—C10—C11—C12	178.82 (15)
C5—C6—C7—C14	−66.50 (18)	O1—C11—C12—C1	−153.30 (16)
C5—C6—C7—C15	176.90 (14)	C10—C11—C12—C1	27.8 (2)
C5—C6—C7—C8	58.73 (16)	C3—C1—C12—C11	156.43 (13)
C3—C1—C8—C9	−163.00 (11)	C2—C1—C12—C11	88.68 (15)
C2—C1—C8—C9	−94.06 (13)	C8—C1—C12—C11	−50.76 (17)
C12—C1—C8—C9	44.19 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···O1i	0.99	2.60	3.541 (2)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2B⋯O1i	0.99	2.60	3.541 (2)	160

Symmetry code: (i) .