The title compound, C
16H
17BrO
2, exhibits C—H
O, C—H
Br and O—H
O hydrogen-bonding interactions. The molecule contains six-membered rings with twist and boat conformations in addition to the benzene ring.
Supporting information
CCDC reference: 200765
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.043
- wR factor = 0.118
- Data-to-parameter ratio = 14.5
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Data collection: COLLECT (Nonius, 1998); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PARST95 (Nardelli, 1995), PLATON (Spek, 1990) and WinGX (Farrugia, 1999).
1S(
R),2S(
R),3S(
R),10S(
R),12
R(
S),13
R(
S),14
R(
S),17S(
R)-13-Bromo-11-
oxapentacyclo[8.7.0.0
2,14.0
4,9.0
12,17]heptadeca-4,6,8-trien-3-ol
top
Crystal data top
C16H17BrO2 | F(000) = 656 |
Mr = 321.21 | Dx = 1.593 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54180 Å |
Hall symbol: -P 2ybc | Cell parameters from 2637 reflections |
a = 11.651 (5) Å | θ = 3.9–96.6° |
b = 10.835 (5) Å | µ = 4.14 mm−1 |
c = 11.029 (5) Å | T = 293 K |
β = 105.801 (5)° | Prism, colorless |
V = 1339.7 (10) Å3 | 0.20 × 0.15 × 0.06 mm |
Z = 4 | |
Data collection top
Nonius KappaCCD diffractometer | 2511 independent reflections |
Radiation source: fine-focus sealed tube | 2209 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.100 |
Detector resolution: 9.0 pixels mm-1 | θmax = 69.6°, θmin = 3.9° |
φ and ω scans | h = −14→14 |
Absorption correction: multi-scan (SORTEV; Blessing, 1995) | k = −13→13 |
Tmin = 0.484, Tmax = 0.780 | l = −13→13 |
33118 measured reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.043 | H-atom parameters constrained |
wR(F2) = 0.118 | w = 1/[σ2(Fo2) + (0.0631P)2 + 0.6924P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
2511 reflections | Δρmax = 0.51 e Å−3 |
173 parameters | Δρmin = −0.42 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0040 (5) |
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 | x | y | z | Uiso*/Ueq | |
Br | 0.44752 (3) | 0.27591 (5) | 0.88086 (4) | 0.0918 (2) | |
O1 | 0.14347 (13) | 0.11701 (15) | 0.91178 (14) | 0.0467 (4) | |
O2 | 0.0047 (2) | 0.2033 (2) | 0.49226 (19) | 0.0775 (7) | |
H2 | 0.0627 | 0.2267 | 0.4698 | 0.116* | |
C1 | −0.0495 (2) | 0.0599 (2) | 0.7704 (2) | 0.0457 (5) | |
C16 | 0.2865 (2) | 0.2048 (3) | 0.8160 (2) | 0.0541 (6) | |
H16 | 0.2277 | 0.2706 | 0.8112 | 0.065* | |
C14 | 0.0734 (2) | 0.0173 (2) | 0.8368 (2) | 0.0447 (5) | |
H14 | 0.0683 | −0.0519 | 0.8923 | 0.054* | |
C13 | 0.1491 (2) | −0.0198 (2) | 0.7517 (2) | 0.0492 (5) | |
H13 | 0.1271 | −0.1013 | 0.7141 | 0.059* | |
C8 | 0.1472 (2) | 0.0803 (2) | 0.6503 (2) | 0.0509 (6) | |
H8 | 0.1420 | 0.0362 | 0.5714 | 0.061* | |
C2 | −0.1470 (2) | 0.0262 (3) | 0.8130 (3) | 0.0574 (6) | |
H2A | −0.1352 | −0.0209 | 0.8858 | 0.069* | |
C15 | 0.26580 (19) | 0.1052 (2) | 0.9059 (2) | 0.0488 (5) | |
H15 | 0.3224 | 0.1125 | 0.9895 | 0.059* | |
C6 | −0.0663 (2) | 0.1300 (2) | 0.6612 (2) | 0.0467 (5) | |
C9 | 0.2681 (2) | 0.1499 (3) | 0.6844 (2) | 0.0603 (7) | |
H9 | 0.2671 | 0.2155 | 0.6230 | 0.072* | |
C7 | 0.0411 (2) | 0.1727 (3) | 0.6225 (2) | 0.0505 (6) | |
H7 | 0.0697 | 0.2487 | 0.6691 | 0.061* | |
C4 | −0.2775 (2) | 0.1305 (3) | 0.6406 (3) | 0.0713 (8) | |
H4 | −0.3541 | 0.1551 | 0.5971 | 0.086* | |
C12 | 0.2725 (2) | −0.0208 (3) | 0.8483 (2) | 0.0552 (6) | |
H12 | 0.2753 | −0.0853 | 0.9114 | 0.066* | |
C5 | −0.1818 (2) | 0.1639 (3) | 0.5955 (3) | 0.0607 (7) | |
H5 | −0.1948 | 0.2090 | 0.5212 | 0.073* | |
C3 | −0.2607 (3) | 0.0617 (3) | 0.7485 (3) | 0.0701 (8) | |
H3 | −0.3254 | 0.0393 | 0.7778 | 0.084* | |
C10 | 0.3661 (3) | 0.0554 (4) | 0.6829 (3) | 0.0810 (10) | |
H10A | 0.3458 | 0.0112 | 0.6034 | 0.097* | |
H10B | 0.4414 | 0.0974 | 0.6918 | 0.097* | |
C11 | 0.3774 (3) | −0.0353 (4) | 0.7916 (3) | 0.0787 (9) | |
H11A | 0.3794 | −0.1190 | 0.7612 | 0.094* | |
H11B | 0.4515 | −0.0201 | 0.8559 | 0.094* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br | 0.0503 (3) | 0.1266 (4) | 0.0880 (3) | −0.03494 (18) | 0.00119 (18) | 0.0107 (2) |
O1 | 0.0388 (8) | 0.0586 (10) | 0.0426 (8) | −0.0024 (7) | 0.0105 (6) | −0.0057 (7) |
O2 | 0.0614 (12) | 0.1082 (17) | 0.0499 (10) | −0.0247 (11) | −0.0067 (9) | 0.0298 (10) |
C1 | 0.0409 (11) | 0.0493 (12) | 0.0447 (11) | −0.0016 (9) | 0.0080 (9) | −0.0045 (9) |
C16 | 0.0343 (12) | 0.0712 (16) | 0.0528 (13) | −0.0079 (10) | 0.0050 (10) | 0.0047 (11) |
C14 | 0.0442 (12) | 0.0471 (12) | 0.0413 (11) | −0.0023 (9) | 0.0089 (9) | 0.0022 (9) |
C13 | 0.0471 (13) | 0.0511 (13) | 0.0478 (12) | 0.0040 (10) | 0.0103 (10) | −0.0028 (10) |
C8 | 0.0489 (13) | 0.0656 (15) | 0.0383 (11) | −0.0023 (11) | 0.0119 (9) | −0.0035 (10) |
C2 | 0.0497 (13) | 0.0685 (16) | 0.0555 (13) | −0.0050 (12) | 0.0171 (11) | −0.0011 (12) |
C15 | 0.0347 (11) | 0.0659 (14) | 0.0431 (11) | 0.0010 (10) | 0.0056 (9) | 0.0005 (10) |
C6 | 0.0430 (12) | 0.0470 (12) | 0.0455 (11) | −0.0010 (9) | 0.0043 (9) | −0.0018 (9) |
C9 | 0.0448 (13) | 0.089 (2) | 0.0481 (13) | −0.0034 (13) | 0.0140 (10) | 0.0101 (13) |
C7 | 0.0458 (13) | 0.0567 (14) | 0.0418 (12) | −0.0066 (10) | −0.0003 (10) | 0.0067 (9) |
C4 | 0.0370 (13) | 0.089 (2) | 0.0804 (19) | 0.0057 (13) | 0.0029 (12) | −0.0046 (16) |
C12 | 0.0462 (13) | 0.0630 (15) | 0.0544 (13) | 0.0102 (11) | 0.0099 (10) | 0.0040 (11) |
C5 | 0.0512 (14) | 0.0634 (16) | 0.0591 (14) | 0.0030 (12) | 0.0005 (11) | 0.0038 (12) |
C3 | 0.0441 (14) | 0.092 (2) | 0.0762 (18) | −0.0051 (14) | 0.0194 (13) | −0.0035 (16) |
C10 | 0.0539 (16) | 0.127 (3) | 0.0695 (18) | 0.0070 (17) | 0.0295 (14) | −0.0059 (18) |
C11 | 0.0561 (16) | 0.101 (2) | 0.081 (2) | 0.0242 (16) | 0.0227 (15) | −0.0026 (18) |
Geometric parameters (Å, º) top
Br—C16 | 1.973 (3) | C2—H2A | 0.930 |
O1—C15 | 1.450 (3) | C15—C12 | 1.517 (4) |
O1—C14 | 1.467 (3) | C15—H15 | 0.980 |
O2—C7 | 1.422 (3) | C6—C5 | 1.393 (4) |
O2—H2 | 0.820 | C6—C7 | 1.502 (3) |
C1—C6 | 1.391 (3) | C9—C10 | 1.537 (5) |
C1—C2 | 1.392 (3) | C9—H9 | 0.980 |
C1—C14 | 1.492 (3) | C7—H7 | 0.980 |
C16—C9 | 1.529 (4) | C4—C3 | 1.373 (5) |
C16—C15 | 1.529 (4) | C4—C5 | 1.386 (4) |
C16—H16 | 0.980 | C4—H4 | 0.930 |
C14—C13 | 1.506 (3) | C12—C11 | 1.526 (4) |
C14—H14 | 0.980 | C12—H12 | 0.980 |
C13—C12 | 1.539 (3) | C5—H5 | 0.930 |
C13—C8 | 1.554 (3) | C3—H3 | 0.930 |
C13—H13 | 0.980 | C10—C11 | 1.528 (5) |
C8—C9 | 1.551 (4) | C10—H10A | 0.970 |
C8—C7 | 1.554 (4) | C10—H10B | 0.970 |
C8—H8 | 0.980 | C11—H11A | 0.970 |
C2—C3 | 1.377 (4) | C11—H11B | 0.970 |
| | | |
C15—O1—C14 | 108.24 (17) | C5—C6—C7 | 122.2 (2) |
C7—O2—H2 | 109.5 | C16—C9—C10 | 111.0 (2) |
C6—C1—C2 | 120.0 (2) | C16—C9—C8 | 107.62 (19) |
C6—C1—C14 | 119.0 (2) | C10—C9—C8 | 107.5 (3) |
C2—C1—C14 | 121.0 (2) | C16—C9—H9 | 110.2 |
C9—C16—C15 | 109.6 (2) | C10—C9—H9 | 110.2 |
C9—C16—Br | 111.69 (17) | C8—C9—H9 | 110.2 |
C15—C16—Br | 110.04 (16) | O2—C7—C6 | 108.46 (18) |
C9—C16—H16 | 108.5 | O2—C7—C8 | 110.6 (2) |
C15—C16—H16 | 108.5 | C6—C7—C8 | 115.2 (2) |
Br—C16—H16 | 108.5 | O2—C7—H7 | 107.4 |
O1—C14—C1 | 111.17 (18) | C6—C7—H7 | 107.4 |
O1—C14—C13 | 102.53 (17) | C8—C7—H7 | 107.4 |
C1—C14—C13 | 115.00 (19) | C3—C4—C5 | 120.9 (3) |
O1—C14—H14 | 109.3 | C3—C4—H4 | 119.5 |
C1—C14—H14 | 109.3 | C5—C4—H4 | 119.5 |
C13—C14—H14 | 109.3 | C15—C12—C11 | 113.7 (3) |
C14—C13—C12 | 99.55 (19) | C15—C12—C13 | 97.96 (19) |
C14—C13—C8 | 111.5 (2) | C11—C12—C13 | 114.8 (2) |
C12—C13—C8 | 109.3 (2) | C15—C12—H12 | 109.9 |
C14—C13—H13 | 111.9 | C11—C12—H12 | 109.9 |
C12—C13—H13 | 111.9 | C13—C12—H12 | 109.9 |
C8—C13—H13 | 111.9 | C4—C5—C6 | 120.1 (3) |
C9—C8—C13 | 109.3 (2) | C4—C5—H5 | 120.0 |
C9—C8—C7 | 110.8 (2) | C6—C5—H5 | 120.0 |
C13—C8—C7 | 116.5 (2) | C4—C3—C2 | 119.3 (3) |
C9—C8—H8 | 106.5 | C4—C3—H3 | 120.3 |
C13—C8—H8 | 106.5 | C2—C3—H3 | 120.3 |
C7—C8—H8 | 106.5 | C11—C10—C9 | 109.0 (2) |
C3—C2—C1 | 120.8 (3) | C11—C10—H10A | 109.9 |
C3—C2—H2A | 119.6 | C9—C10—H10A | 109.9 |
C1—C2—H2A | 119.6 | C11—C10—H10B | 109.9 |
O1—C15—C12 | 105.14 (19) | C9—C10—H10B | 109.9 |
O1—C15—C16 | 107.29 (19) | H10A—C10—H10B | 108.3 |
C12—C15—C16 | 109.2 (2) | C12—C11—C10 | 110.4 (2) |
O1—C15—H15 | 111.6 | C12—C11—H11A | 109.6 |
C12—C15—H15 | 111.6 | C10—C11—H11A | 109.6 |
C16—C15—H15 | 111.6 | C12—C11—H11B | 109.6 |
C1—C6—C5 | 118.9 (2) | C10—C11—H11B | 109.6 |
C1—C6—C7 | 118.8 (2) | H11A—C11—H11B | 108.1 |
| | | |
C15—O1—C14—C1 | −143.87 (19) | Br—C16—C9—C8 | 171.94 (18) |
C15—O1—C14—C13 | −20.5 (2) | C13—C8—C9—C16 | −57.5 (3) |
C6—C1—C14—O1 | 78.4 (2) | C7—C8—C9—C16 | 72.2 (3) |
C2—C1—C14—O1 | −104.3 (2) | C13—C8—C9—C10 | 62.1 (3) |
C6—C1—C14—C13 | −37.5 (3) | C7—C8—C9—C10 | −168.2 (2) |
C2—C1—C14—C13 | 139.7 (2) | C1—C6—C7—O2 | 160.2 (2) |
O1—C14—C13—C12 | 44.0 (2) | C5—C6—C7—O2 | −23.4 (3) |
C1—C14—C13—C12 | 164.7 (2) | C1—C6—C7—C8 | 35.6 (3) |
O1—C14—C13—C8 | −71.3 (2) | C5—C6—C7—C8 | −148.0 (2) |
C1—C14—C13—C8 | 49.5 (3) | C9—C8—C7—O2 | 90.5 (2) |
C14—C13—C8—C9 | 106.2 (2) | C13—C8—C7—O2 | −143.7 (2) |
C12—C13—C8—C9 | −2.9 (3) | C9—C8—C7—C6 | −146.1 (2) |
C14—C13—C8—C7 | −20.3 (3) | C13—C8—C7—C6 | −20.3 (3) |
C12—C13—C8—C7 | −129.4 (2) | O1—C15—C12—C11 | 159.9 (2) |
C14—C1—C2—C3 | −177.4 (3) | C16—C15—C12—C11 | 45.0 (3) |
C14—O1—C15—C12 | −11.9 (2) | O1—C15—C12—C13 | 38.3 (2) |
C14—O1—C15—C16 | 104.3 (2) | C16—C15—C12—C13 | −76.6 (2) |
C9—C16—C15—O1 | −95.9 (2) | C14—C13—C12—C15 | −49.9 (2) |
Br—C16—C15—O1 | 140.95 (16) | C8—C13—C12—C15 | 67.0 (2) |
C9—C16—C15—C12 | 17.6 (3) | C14—C13—C12—C11 | −170.7 (2) |
Br—C16—C15—C12 | −105.6 (2) | C8—C13—C12—C11 | −53.8 (3) |
C14—C1—C6—C5 | 176.5 (2) | C7—C6—C5—C4 | −174.8 (3) |
C2—C1—C6—C7 | 175.7 (2) | C16—C9—C10—C11 | 49.7 (4) |
C14—C1—C6—C7 | −7.0 (3) | C8—C9—C10—C11 | −67.8 (3) |
C15—C16—C9—C10 | −67.7 (3) | C15—C12—C11—C10 | −62.7 (3) |
Br—C16—C9—C10 | 54.5 (3) | C13—C12—C11—C10 | 49.0 (4) |
C15—C16—C9—C8 | 49.7 (3) | C9—C10—C11—C12 | 12.1 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···O1 | 0.98 | 2.95 | 3.145 (3) | 92 |
C5—H5···O2 | 0.93 | 2.43 | 2.748 (4) | 100 |
C10—H10B···Br | 0.97 | 2.83 | 3.202 (4) | 104 |
C9—H9···O1i | 0.98 | 2.99 | 3.893 (3) | 153 |
O2—H2···O1i | 0.82 | 2.12 | 2.824 (3) | 144 |
C4—H4···Brii | 0.93 | 2.93 | 3.808 (3) | 157 |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x−1, −y+1/2, z−1/2. |