Methyl rac-(1S*,11R*,12S*,14S*)-12-hydroxy-14-methyl-15-oxobi­cyclo­[9.3.1]­penta­decane-1-carboxyl­ate

The mol­ecule of the title compound, C₁₈H₃₀O₄, can be described as a trans-fused bicyclic system. The carbonyl group lies on the same side as the methoxy­carbonyl group, while the OH group is on the opposite side. The six-membered ring has a twist formed conformation, presumably due to the presence of the methyl group next to a bulky methoxy­carbonyl group. There are two local pseudo-twofold axes, one passing through two C atoms, the other through the mid-points of two C-C bonds.

Key indicators

• Single-crystal X-ray study
• T = 291 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.042
• wR factor = 0.131
• Data-to-parameter ratio = 19.8

checkCIF/PLATON results

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Computing details

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELTXL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97, PARST95 (Nardelli, 1995) and PLATON (Spek, 2001).

Methyl rac-(1S*,11R*,12S*,14S*)-12-hydroxy-14-methyl-15- oxobicyclo[9.3.1]pentadecane-1-carboxylate

Crystal data

C18H30O4	Z = 2
Mr = 310.42	F(000) = 340
Triclinic, P1	Dx = 1.171 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4865 (5) Å	Cell parameters from 13476 reflections
b = 8.8025 (2) Å	θ = 3.4–27.5°
c = 12.2034 (2) Å	µ = 0.08 mm^−1
α = 89.9661 (7)°	T = 291 K
β = 87.4671 (8)°	Block, colorless
γ = 75.2109 (7)°	0.45 × 0.40 × 0.25 mm
V = 880.51 (6) Å^3

Data collection

Nonius KappaCCD diffractometer	2991 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.023
Graphite monochromator	θmax = 27.5°, θmin = 3.4°
Detector resolution: 19 vertical, 18 horizontal pixels mm^-1	h = −11→11
488 frames via ω–rotation (Δω=1°) and two times 20 s per frame (four sets at different κ–angles) scans	k = −10→11
13476 measured reflections	l = −15→15
4008 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	w = 1/[σ^2(Fo^2) + (0.0697P)^2 + 0.0293P] where P = (Fo^2 + 2Fc^2)/3
4008 reflections	(Δ/σ)max < 0.001
202 parameters	Δρmax = 0.29 e Å^−3
0 restraints	Δρmin = −0.15 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	−0.31386 (12)	−0.10899 (10)	0.21670 (9)	0.0662 (3)
H1	−0.2535	−0.1981	0.2159	0.099*
O2	0.06860 (10)	0.17285 (10)	0.11527 (7)	0.0533 (2)
O3	−0.16305 (14)	0.56243 (10)	0.21298 (10)	0.0741 (3)
O4	−0.21265 (13)	0.42714 (10)	0.06992 (8)	0.0637 (3)
C1	−0.16077 (13)	0.28967 (12)	0.23693 (10)	0.0423 (3)
C2	−0.09362 (15)	0.30501 (14)	0.35146 (10)	0.0484 (3)
H2A	−0.1710	0.3892	0.3913	0.058*
H2B	−0.0905	0.2086	0.3909	0.058*
C3	0.07508 (16)	0.33693 (15)	0.35514 (11)	0.0543 (3)
H3A	0.0641	0.4486	0.3463	0.065*
H3B	0.1435	0.2825	0.2942	0.065*
C4	0.15865 (18)	0.28398 (17)	0.46244 (12)	0.0619 (4)
H4A	0.2538	0.3255	0.4658	0.074*
H4B	0.0843	0.3294	0.5234	0.074*
C5	0.21184 (17)	0.10666 (18)	0.47682 (11)	0.0608 (4)
H5A	0.2496	0.0849	0.5505	0.073*
H5B	0.1177	0.0645	0.4700	0.073*
C6	0.34602 (16)	0.02123 (17)	0.39527 (12)	0.0582 (3)
H6A	0.4485	0.0405	0.4156	0.070*
H6B	0.3225	0.0655	0.3232	0.070*
C7	0.36684 (16)	−0.15559 (17)	0.38796 (12)	0.0599 (4)
H7A	0.3718	−0.1978	0.4615	0.072*
H7B	0.4698	−0.2034	0.3491	0.072*
C8	0.22979 (16)	−0.20085 (16)	0.32982 (11)	0.0561 (3)
H8A	0.1261	−0.1451	0.3644	0.067*
H8B	0.2407	−0.3125	0.3390	0.067*
C9	0.22838 (15)	−0.16438 (15)	0.20745 (11)	0.0536 (3)
H9A	0.2624	−0.0681	0.1966	0.064*
H9B	0.3087	−0.2480	0.1692	0.064*
C10	0.06503 (15)	−0.14600 (14)	0.15487 (11)	0.0499 (3)
H10A	0.0302	−0.2417	0.1666	0.060*
H10B	0.0811	−0.1350	0.0764	0.060*
C11	−0.07227 (14)	−0.00687 (12)	0.19715 (10)	0.0411 (3)
H11	−0.0818	−0.0172	0.2770	0.049*
C12	−0.24025 (15)	−0.00947 (14)	0.15222 (11)	0.0492 (3)
H12	−0.2240	−0.0489	0.0764	0.059*
C13	−0.35889 (16)	0.15327 (15)	0.15527 (12)	0.0550 (3)
H13A	−0.3458	0.2065	0.0872	0.066*
H13B	−0.4697	0.1421	0.1609	0.066*
C14	−0.33232 (14)	0.25287 (14)	0.25060 (11)	0.0500 (3)
H14	−0.3292	0.1882	0.3162	0.060*
C15	−0.04149 (14)	0.15218 (13)	0.17523 (9)	0.0397 (3)
C16	−0.17598 (15)	0.44134 (14)	0.17334 (11)	0.0510 (3)
C17	−0.2385 (3)	0.5674 (2)	0.00337 (16)	0.0887 (6)
H17A	−0.3344	0.6435	0.0309	0.133*
H17B	−0.2526	0.5408	−0.0712	0.133*
H17C	−0.1457	0.6106	0.0064	0.133*
C18	−0.47207 (16)	0.40020 (17)	0.27153 (15)	0.0697 (4)
H18A	−0.4875	0.4621	0.2062	0.104*
H18B	−0.4459	0.4609	0.3302	0.104*
H18C	−0.5705	0.3700	0.2913	0.104*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0617 (6)	0.0394 (5)	0.1002 (8)	−0.0206 (4)	0.0129 (5)	0.0025 (5)
O2	0.0569 (5)	0.0455 (5)	0.0573 (5)	−0.0160 (4)	0.0146 (4)	0.0005 (4)
O3	0.1020 (8)	0.0311 (5)	0.0919 (8)	−0.0201 (5)	−0.0164 (6)	0.0058 (5)
O4	0.0862 (7)	0.0406 (5)	0.0664 (6)	−0.0191 (5)	−0.0116 (5)	0.0159 (4)
C1	0.0456 (6)	0.0286 (5)	0.0519 (6)	−0.0094 (4)	0.0039 (5)	0.0008 (5)
C2	0.0536 (7)	0.0392 (6)	0.0516 (7)	−0.0120 (5)	0.0065 (5)	−0.0060 (5)
C3	0.0608 (8)	0.0453 (7)	0.0597 (8)	−0.0195 (6)	−0.0002 (6)	−0.0033 (6)
C4	0.0655 (8)	0.0667 (9)	0.0560 (8)	−0.0219 (7)	−0.0018 (6)	−0.0126 (7)
C5	0.0616 (8)	0.0704 (9)	0.0490 (7)	−0.0142 (7)	−0.0028 (6)	0.0024 (6)
C6	0.0479 (7)	0.0678 (9)	0.0593 (8)	−0.0154 (6)	−0.0023 (6)	0.0035 (7)
C7	0.0487 (7)	0.0634 (9)	0.0616 (8)	−0.0035 (6)	−0.0024 (6)	0.0106 (6)
C8	0.0531 (7)	0.0476 (7)	0.0644 (8)	−0.0073 (6)	−0.0005 (6)	0.0086 (6)
C9	0.0498 (7)	0.0465 (7)	0.0584 (8)	−0.0023 (5)	0.0048 (6)	−0.0032 (6)
C10	0.0559 (7)	0.0351 (6)	0.0553 (7)	−0.0059 (5)	0.0012 (6)	−0.0062 (5)
C11	0.0479 (6)	0.0295 (5)	0.0449 (6)	−0.0085 (4)	0.0010 (5)	0.0006 (4)
C12	0.0525 (7)	0.0367 (6)	0.0606 (7)	−0.0161 (5)	0.0004 (6)	−0.0017 (5)
C13	0.0502 (7)	0.0454 (7)	0.0715 (9)	−0.0148 (6)	−0.0085 (6)	0.0076 (6)
C14	0.0449 (6)	0.0351 (6)	0.0679 (8)	−0.0073 (5)	0.0041 (6)	0.0019 (5)
C15	0.0454 (6)	0.0327 (6)	0.0412 (6)	−0.0106 (4)	−0.0013 (5)	0.0004 (4)
C16	0.0545 (7)	0.0323 (6)	0.0660 (8)	−0.0106 (5)	−0.0013 (6)	0.0048 (6)
C17	0.1232 (15)	0.0583 (9)	0.0864 (12)	−0.0237 (9)	−0.0233 (10)	0.0335 (9)
C18	0.0505 (8)	0.0480 (8)	0.1030 (12)	−0.0011 (6)	0.0085 (7)	−0.0021 (8)

Geometric parameters (Å, º)

O1—C12	1.4184 (15)	C7—H7B	0.9700
O1—H1	0.8200	C8—C9	1.5272 (19)
O2—C15	1.2114 (13)	C8—H8A	0.9700
O3—C16	1.2030 (16)	C8—H8B	0.9700
O4—C16	1.3267 (16)	C9—C10	1.5243 (18)
O4—C17	1.4521 (16)	C9—H9A	0.9700
C1—C16	1.5235 (15)	C9—H9B	0.9700
C1—C15	1.5378 (16)	C10—C11	1.5307 (16)
C1—C2	1.5512 (18)	C10—H10A	0.9700
C1—C14	1.5721 (16)	C10—H10B	0.9700
C2—C3	1.5302 (18)	C11—C15	1.5100 (15)
C2—H2A	0.9700	C11—C12	1.5553 (17)
C2—H2B	0.9700	C11—H11	0.9800
C3—C4	1.532 (2)	C12—C13	1.5257 (18)
C3—H3A	0.9700	C12—H12	0.9800
C3—H3B	0.9700	C13—C14	1.516 (2)
C4—C5	1.522 (2)	C13—H13A	0.9700
C4—H4A	0.9700	C13—H13B	0.9700
C4—H4B	0.9700	C14—C18	1.5303 (18)
C5—C6	1.5219 (19)	C14—H14	0.9800
C5—H5A	0.9700	C17—H17A	0.9600
C5—H5B	0.9700	C17—H17B	0.9600
C6—C7	1.523 (2)	C17—H17C	0.9600
C6—H6A	0.9700	C18—H18A	0.9600
C6—H6B	0.9700	C18—H18B	0.9600
C7—C8	1.525 (2)	C18—H18C	0.9600
C7—H7A	0.9700
C12—O1—H1	109.5	C8—C9—H9A	108.4
C16—O4—C17	116.86 (12)	C10—C9—H9B	108.4
C16—C1—C15	110.17 (10)	C8—C9—H9B	108.4
C16—C1—C2	110.16 (10)	H9A—C9—H9B	107.5
C15—C1—C2	108.01 (9)	C9—C10—C11	115.43 (10)
C16—C1—C14	109.77 (9)	C9—C10—H10A	108.4
C15—C1—C14	108.95 (9)	C11—C10—H10A	108.4
C2—C1—C14	109.74 (10)	C9—C10—H10B	108.4
C3—C2—C1	117.51 (10)	C11—C10—H10B	108.4
C3—C2—H2A	107.9	H10A—C10—H10B	107.5
C1—C2—H2A	107.9	C15—C11—C10	114.47 (10)
C3—C2—H2B	107.9	C15—C11—C12	108.85 (9)
C1—C2—H2B	107.9	C10—C11—C12	112.38 (10)
H2A—C2—H2B	107.2	C15—C11—H11	106.9
C2—C3—C4	112.79 (11)	C10—C11—H11	106.9
C2—C3—H3A	109.0	C12—C11—H11	106.9
C4—C3—H3A	109.0	O1—C12—C13	107.07 (10)
C2—C3—H3B	109.0	O1—C12—C11	110.36 (10)
C4—C3—H3B	109.0	C13—C12—C11	111.98 (9)
H3A—C3—H3B	107.8	O1—C12—H12	109.1
C5—C4—C3	114.61 (12)	C13—C12—H12	109.1
C5—C4—H4A	108.6	C11—C12—H12	109.1
C3—C4—H4A	108.6	C14—C13—C12	112.34 (10)
C5—C4—H4B	108.6	C14—C13—H13A	109.1
C3—C4—H4B	108.6	C12—C13—H13A	109.1
H4A—C4—H4B	107.6	C14—C13—H13B	109.1
C6—C5—C4	114.55 (12)	C12—C13—H13B	109.1
C6—C5—H5A	108.6	H13A—C13—H13B	107.9
C4—C5—H5A	108.6	C13—C14—C18	113.32 (11)
C6—C5—H5B	108.6	C13—C14—C1	110.54 (10)
C4—C5—H5B	108.6	C18—C14—C1	113.00 (10)
H5A—C5—H5B	107.6	C13—C14—H14	106.5
C5—C6—C7	114.54 (12)	C18—C14—H14	106.5
C5—C6—H6A	108.6	C1—C14—H14	106.5
C7—C6—H6A	108.6	O2—C15—C11	123.91 (10)
C5—C6—H6B	108.6	O2—C15—C1	121.43 (10)
C7—C6—H6B	108.6	C11—C15—C1	114.65 (9)
H6A—C6—H6B	107.6	O3—C16—O4	123.45 (11)
C6—C7—C8	113.38 (11)	O3—C16—C1	124.16 (13)
C6—C7—H7A	108.9	O4—C16—C1	112.32 (10)
C8—C7—H7A	108.9	O4—C17—H17A	109.5
C6—C7—H7B	108.9	O4—C17—H17B	109.5
C8—C7—H7B	108.9	H17A—C17—H17B	109.5
H7A—C7—H7B	107.7	O4—C17—H17C	109.5
C7—C8—C9	113.51 (11)	H17A—C17—H17C	109.5
C7—C8—H8A	108.9	H17B—C17—H17C	109.5
C9—C8—H8A	108.9	C14—C18—H18A	109.5
C7—C8—H8B	108.9	C14—C18—H18B	109.5
C9—C8—H8B	108.9	H18A—C18—H18B	109.5
H8A—C8—H8B	107.7	C14—C18—H18C	109.5
C10—C9—C8	115.56 (11)	H18A—C18—H18C	109.5
C10—C9—H9A	108.4	H18B—C18—H18C	109.5
C16—C1—C2—C3	−60.49 (13)	C2—C1—C14—C13	−148.83 (10)
C15—C1—C2—C3	59.88 (13)	C16—C1—C14—C18	−38.24 (15)
C14—C1—C2—C3	178.54 (10)	C15—C1—C14—C18	−158.95 (11)
C1—C2—C3—C4	−156.29 (11)	C2—C1—C14—C18	82.97 (13)
C2—C3—C4—C5	69.42 (15)	C10—C11—C15—O2	10.92 (16)
C3—C4—C5—C6	65.95 (16)	C12—C11—C15—O2	−115.77 (12)
C4—C5—C6—C7	−163.86 (12)	C10—C11—C15—C1	−168.24 (10)
C5—C6—C7—C8	72.65 (15)	C12—C11—C15—C1	65.07 (12)
C6—C7—C8—C9	68.18 (15)	C16—C1—C15—O2	27.94 (15)
C7—C8—C9—C10	−157.22 (11)	C2—C1—C15—O2	−92.43 (13)
C8—C9—C10—C11	64.50 (14)	C14—C1—C15—O2	148.42 (11)
C9—C10—C11—C15	63.32 (14)	C16—C1—C15—C11	−152.88 (10)
C9—C10—C11—C12	−171.84 (10)	C2—C1—C15—C11	86.75 (11)
C15—C11—C12—O1	−148.70 (10)	C14—C1—C15—C11	−32.41 (13)
C10—C11—C12—O1	83.42 (12)	C17—O4—C16—O3	−0.3 (2)
C15—C11—C12—C13	−29.53 (14)	C17—O4—C16—C1	176.84 (13)
C10—C11—C12—C13	−157.41 (11)	C15—C1—C16—O3	−130.15 (14)
O1—C12—C13—C14	89.05 (12)	C2—C1—C16—O3	−11.08 (17)
C11—C12—C13—C14	−32.04 (15)	C14—C1—C16—O3	109.87 (14)
C12—C13—C14—C18	−166.70 (11)	C15—C1—C16—O4	52.74 (13)
C12—C13—C14—C1	65.27 (13)	C2—C1—C16—O4	171.81 (10)
C16—C1—C14—C13	89.96 (12)	C14—C1—C16—O4	−67.24 (13)
C15—C1—C14—C13	−30.75 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3^i	0.82	2.05	2.848 (1)	164

Symmetry code: (i) x, y−1, z.