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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803023420/na6251sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803023420/na6251Isup2.hkl
Contains datablock I

CCDC reference: 227008

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

No syntax errors found


No errors found in this datablock

Computing details top

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 top
Crystal data top
C18H30O4Z = 2
Mr = 310.42F(000) = 340
Triclinic, P1Dx = 1.171 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.4865 (5) ÅCell parameters from 13476 reflections
b = 8.8025 (2) Åθ = 3.4–27.5°
c = 12.2034 (2) ŵ = 0.08 mm1
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) Å3
Data collection top
Nonius KappaCCD
diffractometer
2991 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.023
Graphite monochromatorθmax = 27.5°, θmin = 3.4°
Detector resolution: 19 vertical, 18 horizontal pixels mm-1h = 1111
488 frames via ω–rotation (Δω=1°) and two times 20 s per frame (four sets at different κ–angles) scansk = 1011
13476 measured reflectionsl = 1515
4008 independent reflections
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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131H atoms treated by a mixture of independent and constrained refinement
S = 1.14 w = 1/[σ2(Fo2) + (0.0697P)2 + 0.0293P]
where P = (Fo2 + 2Fc2)/3
4008 reflections(Δ/σ)max < 0.001
202 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = 0.15 e Å3
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
O10.31386 (12)0.10899 (10)0.21670 (9)0.0662 (3)
H10.25350.19810.21590.099*
O20.06860 (10)0.17285 (10)0.11527 (7)0.0533 (2)
O30.16305 (14)0.56243 (10)0.21298 (10)0.0741 (3)
O40.21265 (13)0.42714 (10)0.06992 (8)0.0637 (3)
C10.16077 (13)0.28967 (12)0.23693 (10)0.0423 (3)
C20.09362 (15)0.30501 (14)0.35146 (10)0.0484 (3)
H2A0.17100.38920.39130.058*
H2B0.09050.20860.39090.058*
C30.07508 (16)0.33693 (15)0.35514 (11)0.0543 (3)
H3A0.06410.44860.34630.065*
H3B0.14350.28250.29420.065*
C40.15865 (18)0.28398 (17)0.46244 (12)0.0619 (4)
H4A0.25380.32550.46580.074*
H4B0.08430.32940.52340.074*
C50.21184 (17)0.10666 (18)0.47682 (11)0.0608 (4)
H5A0.24960.08490.55050.073*
H5B0.11770.06450.47000.073*
C60.34602 (16)0.02123 (17)0.39527 (12)0.0582 (3)
H6A0.44850.04050.41560.070*
H6B0.32250.06550.32320.070*
C70.36684 (16)0.15559 (17)0.38796 (12)0.0599 (4)
H7A0.37180.19780.46150.072*
H7B0.46980.20340.34910.072*
C80.22979 (16)0.20085 (16)0.32982 (11)0.0561 (3)
H8A0.12610.14510.36440.067*
H8B0.24070.31250.33900.067*
C90.22838 (15)0.16438 (15)0.20745 (11)0.0536 (3)
H9A0.26240.06810.19660.064*
H9B0.30870.24800.16920.064*
C100.06503 (15)0.14600 (14)0.15487 (11)0.0499 (3)
H10A0.03020.24170.16660.060*
H10B0.08110.13500.07640.060*
C110.07227 (14)0.00687 (12)0.19715 (10)0.0411 (3)
H110.08180.01720.27700.049*
C120.24025 (15)0.00947 (14)0.15222 (11)0.0492 (3)
H120.22400.04890.07640.059*
C130.35889 (16)0.15327 (15)0.15527 (12)0.0550 (3)
H13A0.34580.20650.08720.066*
H13B0.46970.14210.16090.066*
C140.33232 (14)0.25287 (14)0.25060 (11)0.0500 (3)
H140.32920.18820.31620.060*
C150.04149 (14)0.15218 (13)0.17523 (9)0.0397 (3)
C160.17598 (15)0.44134 (14)0.17334 (11)0.0510 (3)
C170.2385 (3)0.5674 (2)0.00337 (16)0.0887 (6)
H17A0.33440.64350.03090.133*
H17B0.25260.54080.07120.133*
H17C0.14570.61060.00640.133*
C180.47207 (16)0.40020 (17)0.27153 (15)0.0697 (4)
H18A0.48750.46210.20620.104*
H18B0.44590.46090.33020.104*
H18C0.57050.37000.29130.104*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0617 (6)0.0394 (5)0.1002 (8)0.0206 (4)0.0129 (5)0.0025 (5)
O20.0569 (5)0.0455 (5)0.0573 (5)0.0160 (4)0.0146 (4)0.0005 (4)
O30.1020 (8)0.0311 (5)0.0919 (8)0.0201 (5)0.0164 (6)0.0058 (5)
O40.0862 (7)0.0406 (5)0.0664 (6)0.0191 (5)0.0116 (5)0.0159 (4)
C10.0456 (6)0.0286 (5)0.0519 (6)0.0094 (4)0.0039 (5)0.0008 (5)
C20.0536 (7)0.0392 (6)0.0516 (7)0.0120 (5)0.0065 (5)0.0060 (5)
C30.0608 (8)0.0453 (7)0.0597 (8)0.0195 (6)0.0002 (6)0.0033 (6)
C40.0655 (8)0.0667 (9)0.0560 (8)0.0219 (7)0.0018 (6)0.0126 (7)
C50.0616 (8)0.0704 (9)0.0490 (7)0.0142 (7)0.0028 (6)0.0024 (6)
C60.0479 (7)0.0678 (9)0.0593 (8)0.0154 (6)0.0023 (6)0.0035 (7)
C70.0487 (7)0.0634 (9)0.0616 (8)0.0035 (6)0.0024 (6)0.0106 (6)
C80.0531 (7)0.0476 (7)0.0644 (8)0.0073 (6)0.0005 (6)0.0086 (6)
C90.0498 (7)0.0465 (7)0.0584 (8)0.0023 (5)0.0048 (6)0.0032 (6)
C100.0559 (7)0.0351 (6)0.0553 (7)0.0059 (5)0.0012 (6)0.0062 (5)
C110.0479 (6)0.0295 (5)0.0449 (6)0.0085 (4)0.0010 (5)0.0006 (4)
C120.0525 (7)0.0367 (6)0.0606 (7)0.0161 (5)0.0004 (6)0.0017 (5)
C130.0502 (7)0.0454 (7)0.0715 (9)0.0148 (6)0.0085 (6)0.0076 (6)
C140.0449 (6)0.0351 (6)0.0679 (8)0.0073 (5)0.0041 (6)0.0019 (5)
C150.0454 (6)0.0327 (6)0.0412 (6)0.0106 (4)0.0013 (5)0.0004 (4)
C160.0545 (7)0.0323 (6)0.0660 (8)0.0106 (5)0.0013 (6)0.0048 (6)
C170.1232 (15)0.0583 (9)0.0864 (12)0.0237 (9)0.0233 (10)0.0335 (9)
C180.0505 (8)0.0480 (8)0.1030 (12)0.0011 (6)0.0085 (7)0.0021 (8)
Geometric parameters (Å, º) top
O1—C121.4184 (15)C7—H7B0.9700
O1—H10.8200C8—C91.5272 (19)
O2—C151.2114 (13)C8—H8A0.9700
O3—C161.2030 (16)C8—H8B0.9700
O4—C161.3267 (16)C9—C101.5243 (18)
O4—C171.4521 (16)C9—H9A0.9700
C1—C161.5235 (15)C9—H9B0.9700
C1—C151.5378 (16)C10—C111.5307 (16)
C1—C21.5512 (18)C10—H10A0.9700
C1—C141.5721 (16)C10—H10B0.9700
C2—C31.5302 (18)C11—C151.5100 (15)
C2—H2A0.9700C11—C121.5553 (17)
C2—H2B0.9700C11—H110.9800
C3—C41.532 (2)C12—C131.5257 (18)
C3—H3A0.9700C12—H120.9800
C3—H3B0.9700C13—C141.516 (2)
C4—C51.522 (2)C13—H13A0.9700
C4—H4A0.9700C13—H13B0.9700
C4—H4B0.9700C14—C181.5303 (18)
C5—C61.5219 (19)C14—H140.9800
C5—H5A0.9700C17—H17A0.9600
C5—H5B0.9700C17—H17B0.9600
C6—C71.523 (2)C17—H17C0.9600
C6—H6A0.9700C18—H18A0.9600
C6—H6B0.9700C18—H18B0.9600
C7—C81.525 (2)C18—H18C0.9600
C7—H7A0.9700
C12—O1—H1109.5C8—C9—H9A108.4
C16—O4—C17116.86 (12)C10—C9—H9B108.4
C16—C1—C15110.17 (10)C8—C9—H9B108.4
C16—C1—C2110.16 (10)H9A—C9—H9B107.5
C15—C1—C2108.01 (9)C9—C10—C11115.43 (10)
C16—C1—C14109.77 (9)C9—C10—H10A108.4
C15—C1—C14108.95 (9)C11—C10—H10A108.4
C2—C1—C14109.74 (10)C9—C10—H10B108.4
C3—C2—C1117.51 (10)C11—C10—H10B108.4
C3—C2—H2A107.9H10A—C10—H10B107.5
C1—C2—H2A107.9C15—C11—C10114.47 (10)
C3—C2—H2B107.9C15—C11—C12108.85 (9)
C1—C2—H2B107.9C10—C11—C12112.38 (10)
H2A—C2—H2B107.2C15—C11—H11106.9
C2—C3—C4112.79 (11)C10—C11—H11106.9
C2—C3—H3A109.0C12—C11—H11106.9
C4—C3—H3A109.0O1—C12—C13107.07 (10)
C2—C3—H3B109.0O1—C12—C11110.36 (10)
C4—C3—H3B109.0C13—C12—C11111.98 (9)
H3A—C3—H3B107.8O1—C12—H12109.1
C5—C4—C3114.61 (12)C13—C12—H12109.1
C5—C4—H4A108.6C11—C12—H12109.1
C3—C4—H4A108.6C14—C13—C12112.34 (10)
C5—C4—H4B108.6C14—C13—H13A109.1
C3—C4—H4B108.6C12—C13—H13A109.1
H4A—C4—H4B107.6C14—C13—H13B109.1
C6—C5—C4114.55 (12)C12—C13—H13B109.1
C6—C5—H5A108.6H13A—C13—H13B107.9
C4—C5—H5A108.6C13—C14—C18113.32 (11)
C6—C5—H5B108.6C13—C14—C1110.54 (10)
C4—C5—H5B108.6C18—C14—C1113.00 (10)
H5A—C5—H5B107.6C13—C14—H14106.5
C5—C6—C7114.54 (12)C18—C14—H14106.5
C5—C6—H6A108.6C1—C14—H14106.5
C7—C6—H6A108.6O2—C15—C11123.91 (10)
C5—C6—H6B108.6O2—C15—C1121.43 (10)
C7—C6—H6B108.6C11—C15—C1114.65 (9)
H6A—C6—H6B107.6O3—C16—O4123.45 (11)
C6—C7—C8113.38 (11)O3—C16—C1124.16 (13)
C6—C7—H7A108.9O4—C16—C1112.32 (10)
C8—C7—H7A108.9O4—C17—H17A109.5
C6—C7—H7B108.9O4—C17—H17B109.5
C8—C7—H7B108.9H17A—C17—H17B109.5
H7A—C7—H7B107.7O4—C17—H17C109.5
C7—C8—C9113.51 (11)H17A—C17—H17C109.5
C7—C8—H8A108.9H17B—C17—H17C109.5
C9—C8—H8A108.9C14—C18—H18A109.5
C7—C8—H8B108.9C14—C18—H18B109.5
C9—C8—H8B108.9H18A—C18—H18B109.5
H8A—C8—H8B107.7C14—C18—H18C109.5
C10—C9—C8115.56 (11)H18A—C18—H18C109.5
C10—C9—H9A108.4H18B—C18—H18C109.5
C16—C1—C2—C360.49 (13)C2—C1—C14—C13148.83 (10)
C15—C1—C2—C359.88 (13)C16—C1—C14—C1838.24 (15)
C14—C1—C2—C3178.54 (10)C15—C1—C14—C18158.95 (11)
C1—C2—C3—C4156.29 (11)C2—C1—C14—C1882.97 (13)
C2—C3—C4—C569.42 (15)C10—C11—C15—O210.92 (16)
C3—C4—C5—C665.95 (16)C12—C11—C15—O2115.77 (12)
C4—C5—C6—C7163.86 (12)C10—C11—C15—C1168.24 (10)
C5—C6—C7—C872.65 (15)C12—C11—C15—C165.07 (12)
C6—C7—C8—C968.18 (15)C16—C1—C15—O227.94 (15)
C7—C8—C9—C10157.22 (11)C2—C1—C15—O292.43 (13)
C8—C9—C10—C1164.50 (14)C14—C1—C15—O2148.42 (11)
C9—C10—C11—C1563.32 (14)C16—C1—C15—C11152.88 (10)
C9—C10—C11—C12171.84 (10)C2—C1—C15—C1186.75 (11)
C15—C11—C12—O1148.70 (10)C14—C1—C15—C1132.41 (13)
C10—C11—C12—O183.42 (12)C17—O4—C16—O30.3 (2)
C15—C11—C12—C1329.53 (14)C17—O4—C16—C1176.84 (13)
C10—C11—C12—C13157.41 (11)C15—C1—C16—O3130.15 (14)
O1—C12—C13—C1489.05 (12)C2—C1—C16—O311.08 (17)
C11—C12—C13—C1432.04 (15)C14—C1—C16—O3109.87 (14)
C12—C13—C14—C18166.70 (11)C15—C1—C16—O452.74 (13)
C12—C13—C14—C165.27 (13)C2—C1—C16—O4171.81 (10)
C16—C1—C14—C1389.96 (12)C14—C1—C16—O467.24 (13)
C15—C1—C14—C1330.75 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O3i0.822.052.848 (1)164
Symmetry code: (i) x, y1, z.
 

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