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The title compound, C16H17BrO2, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802018160/cf6209sup1.cif
Contains datablocks global, 3

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802018160/cf62093sup2.hkl
Contains datablock 3

CCDC reference: 200765

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](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








Computing details top

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),12R(S),13R(S),14R(S),17S(R)-13-Bromo-11- oxapentacyclo[8.7.0.02,14.04,9.012,17]heptadeca-4,6,8-trien-3-ol top
Crystal data top
C16H17BrO2F(000) = 656
Mr = 321.21Dx = 1.593 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ybcCell parameters from 2637 reflections
a = 11.651 (5) Åθ = 3.9–96.6°
b = 10.835 (5) ŵ = 4.14 mm1
c = 11.029 (5) ÅT = 293 K
β = 105.801 (5)°Prism, colorless
V = 1339.7 (10) Å30.20 × 0.15 × 0.06 mm
Z = 4
Data collection top
Nonius KappaCCD
diffractometer
2511 independent reflections
Radiation source: fine-focus sealed tube2209 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.100
Detector resolution: 9.0 pixels mm-1θmax = 69.6°, θmin = 3.9°
φ and ω scansh = 1414
Absorption correction: multi-scan
(SORTEV; Blessing, 1995)
k = 1313
Tmin = 0.484, Tmax = 0.780l = 1313
33118 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H-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 reflectionsΔρmax = 0.51 e Å3
173 parametersΔρmin = 0.42 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction 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
xyzUiso*/Ueq
Br0.44752 (3)0.27591 (5)0.88086 (4)0.0918 (2)
O10.14347 (13)0.11701 (15)0.91178 (14)0.0467 (4)
O20.0047 (2)0.2033 (2)0.49226 (19)0.0775 (7)
H20.06270.22670.46980.116*
C10.0495 (2)0.0599 (2)0.7704 (2)0.0457 (5)
C160.2865 (2)0.2048 (3)0.8160 (2)0.0541 (6)
H160.22770.27060.81120.065*
C140.0734 (2)0.0173 (2)0.8368 (2)0.0447 (5)
H140.06830.05190.89230.054*
C130.1491 (2)0.0198 (2)0.7517 (2)0.0492 (5)
H130.12710.10130.71410.059*
C80.1472 (2)0.0803 (2)0.6503 (2)0.0509 (6)
H80.14200.03620.57140.061*
C20.1470 (2)0.0262 (3)0.8130 (3)0.0574 (6)
H2A0.13520.02090.88580.069*
C150.26580 (19)0.1052 (2)0.9059 (2)0.0488 (5)
H150.32240.11250.98950.059*
C60.0663 (2)0.1300 (2)0.6612 (2)0.0467 (5)
C90.2681 (2)0.1499 (3)0.6844 (2)0.0603 (7)
H90.26710.21550.62300.072*
C70.0411 (2)0.1727 (3)0.6225 (2)0.0505 (6)
H70.06970.24870.66910.061*
C40.2775 (2)0.1305 (3)0.6406 (3)0.0713 (8)
H40.35410.15510.59710.086*
C120.2725 (2)0.0208 (3)0.8483 (2)0.0552 (6)
H120.27530.08530.91140.066*
C50.1818 (2)0.1639 (3)0.5955 (3)0.0607 (7)
H50.19480.20900.52120.073*
C30.2607 (3)0.0617 (3)0.7485 (3)0.0701 (8)
H30.32540.03930.77780.084*
C100.3661 (3)0.0554 (4)0.6829 (3)0.0810 (10)
H10A0.34580.01120.60340.097*
H10B0.44140.09740.69180.097*
C110.3774 (3)0.0353 (4)0.7916 (3)0.0787 (9)
H11A0.37940.11900.76120.094*
H11B0.45150.02010.85590.094*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br0.0503 (3)0.1266 (4)0.0880 (3)0.03494 (18)0.00119 (18)0.0107 (2)
O10.0388 (8)0.0586 (10)0.0426 (8)0.0024 (7)0.0105 (6)0.0057 (7)
O20.0614 (12)0.1082 (17)0.0499 (10)0.0247 (11)0.0067 (9)0.0298 (10)
C10.0409 (11)0.0493 (12)0.0447 (11)0.0016 (9)0.0080 (9)0.0045 (9)
C160.0343 (12)0.0712 (16)0.0528 (13)0.0079 (10)0.0050 (10)0.0047 (11)
C140.0442 (12)0.0471 (12)0.0413 (11)0.0023 (9)0.0089 (9)0.0022 (9)
C130.0471 (13)0.0511 (13)0.0478 (12)0.0040 (10)0.0103 (10)0.0028 (10)
C80.0489 (13)0.0656 (15)0.0383 (11)0.0023 (11)0.0119 (9)0.0035 (10)
C20.0497 (13)0.0685 (16)0.0555 (13)0.0050 (12)0.0171 (11)0.0011 (12)
C150.0347 (11)0.0659 (14)0.0431 (11)0.0010 (10)0.0056 (9)0.0005 (10)
C60.0430 (12)0.0470 (12)0.0455 (11)0.0010 (9)0.0043 (9)0.0018 (9)
C90.0448 (13)0.089 (2)0.0481 (13)0.0034 (13)0.0140 (10)0.0101 (13)
C70.0458 (13)0.0567 (14)0.0418 (12)0.0066 (10)0.0003 (10)0.0067 (9)
C40.0370 (13)0.089 (2)0.0804 (19)0.0057 (13)0.0029 (12)0.0046 (16)
C120.0462 (13)0.0630 (15)0.0544 (13)0.0102 (11)0.0099 (10)0.0040 (11)
C50.0512 (14)0.0634 (16)0.0591 (14)0.0030 (12)0.0005 (11)0.0038 (12)
C30.0441 (14)0.092 (2)0.0762 (18)0.0051 (14)0.0194 (13)0.0035 (16)
C100.0539 (16)0.127 (3)0.0695 (18)0.0070 (17)0.0295 (14)0.0059 (18)
C110.0561 (16)0.101 (2)0.081 (2)0.0242 (16)0.0227 (15)0.0026 (18)
Geometric parameters (Å, º) top
Br—C161.973 (3)C2—H2A0.930
O1—C151.450 (3)C15—C121.517 (4)
O1—C141.467 (3)C15—H150.980
O2—C71.422 (3)C6—C51.393 (4)
O2—H20.820C6—C71.502 (3)
C1—C61.391 (3)C9—C101.537 (5)
C1—C21.392 (3)C9—H90.980
C1—C141.492 (3)C7—H70.980
C16—C91.529 (4)C4—C31.373 (5)
C16—C151.529 (4)C4—C51.386 (4)
C16—H160.980C4—H40.930
C14—C131.506 (3)C12—C111.526 (4)
C14—H140.980C12—H120.980
C13—C121.539 (3)C5—H50.930
C13—C81.554 (3)C3—H30.930
C13—H130.980C10—C111.528 (5)
C8—C91.551 (4)C10—H10A0.970
C8—C71.554 (4)C10—H10B0.970
C8—H80.980C11—H11A0.970
C2—C31.377 (4)C11—H11B0.970
C15—O1—C14108.24 (17)C5—C6—C7122.2 (2)
C7—O2—H2109.5C16—C9—C10111.0 (2)
C6—C1—C2120.0 (2)C16—C9—C8107.62 (19)
C6—C1—C14119.0 (2)C10—C9—C8107.5 (3)
C2—C1—C14121.0 (2)C16—C9—H9110.2
C9—C16—C15109.6 (2)C10—C9—H9110.2
C9—C16—Br111.69 (17)C8—C9—H9110.2
C15—C16—Br110.04 (16)O2—C7—C6108.46 (18)
C9—C16—H16108.5O2—C7—C8110.6 (2)
C15—C16—H16108.5C6—C7—C8115.2 (2)
Br—C16—H16108.5O2—C7—H7107.4
O1—C14—C1111.17 (18)C6—C7—H7107.4
O1—C14—C13102.53 (17)C8—C7—H7107.4
C1—C14—C13115.00 (19)C3—C4—C5120.9 (3)
O1—C14—H14109.3C3—C4—H4119.5
C1—C14—H14109.3C5—C4—H4119.5
C13—C14—H14109.3C15—C12—C11113.7 (3)
C14—C13—C1299.55 (19)C15—C12—C1397.96 (19)
C14—C13—C8111.5 (2)C11—C12—C13114.8 (2)
C12—C13—C8109.3 (2)C15—C12—H12109.9
C14—C13—H13111.9C11—C12—H12109.9
C12—C13—H13111.9C13—C12—H12109.9
C8—C13—H13111.9C4—C5—C6120.1 (3)
C9—C8—C13109.3 (2)C4—C5—H5120.0
C9—C8—C7110.8 (2)C6—C5—H5120.0
C13—C8—C7116.5 (2)C4—C3—C2119.3 (3)
C9—C8—H8106.5C4—C3—H3120.3
C13—C8—H8106.5C2—C3—H3120.3
C7—C8—H8106.5C11—C10—C9109.0 (2)
C3—C2—C1120.8 (3)C11—C10—H10A109.9
C3—C2—H2A119.6C9—C10—H10A109.9
C1—C2—H2A119.6C11—C10—H10B109.9
O1—C15—C12105.14 (19)C9—C10—H10B109.9
O1—C15—C16107.29 (19)H10A—C10—H10B108.3
C12—C15—C16109.2 (2)C12—C11—C10110.4 (2)
O1—C15—H15111.6C12—C11—H11A109.6
C12—C15—H15111.6C10—C11—H11A109.6
C16—C15—H15111.6C12—C11—H11B109.6
C1—C6—C5118.9 (2)C10—C11—H11B109.6
C1—C6—C7118.8 (2)H11A—C11—H11B108.1
C15—O1—C14—C1143.87 (19)Br—C16—C9—C8171.94 (18)
C15—O1—C14—C1320.5 (2)C13—C8—C9—C1657.5 (3)
C6—C1—C14—O178.4 (2)C7—C8—C9—C1672.2 (3)
C2—C1—C14—O1104.3 (2)C13—C8—C9—C1062.1 (3)
C6—C1—C14—C1337.5 (3)C7—C8—C9—C10168.2 (2)
C2—C1—C14—C13139.7 (2)C1—C6—C7—O2160.2 (2)
O1—C14—C13—C1244.0 (2)C5—C6—C7—O223.4 (3)
C1—C14—C13—C12164.7 (2)C1—C6—C7—C835.6 (3)
O1—C14—C13—C871.3 (2)C5—C6—C7—C8148.0 (2)
C1—C14—C13—C849.5 (3)C9—C8—C7—O290.5 (2)
C14—C13—C8—C9106.2 (2)C13—C8—C7—O2143.7 (2)
C12—C13—C8—C92.9 (3)C9—C8—C7—C6146.1 (2)
C14—C13—C8—C720.3 (3)C13—C8—C7—C620.3 (3)
C12—C13—C8—C7129.4 (2)O1—C15—C12—C11159.9 (2)
C14—C1—C2—C3177.4 (3)C16—C15—C12—C1145.0 (3)
C14—O1—C15—C1211.9 (2)O1—C15—C12—C1338.3 (2)
C14—O1—C15—C16104.3 (2)C16—C15—C12—C1376.6 (2)
C9—C16—C15—O195.9 (2)C14—C13—C12—C1549.9 (2)
Br—C16—C15—O1140.95 (16)C8—C13—C12—C1567.0 (2)
C9—C16—C15—C1217.6 (3)C14—C13—C12—C11170.7 (2)
Br—C16—C15—C12105.6 (2)C8—C13—C12—C1153.8 (3)
C14—C1—C6—C5176.5 (2)C7—C6—C5—C4174.8 (3)
C2—C1—C6—C7175.7 (2)C16—C9—C10—C1149.7 (4)
C14—C1—C6—C77.0 (3)C8—C9—C10—C1167.8 (3)
C15—C16—C9—C1067.7 (3)C15—C12—C11—C1062.7 (3)
Br—C16—C9—C1054.5 (3)C13—C12—C11—C1049.0 (4)
C15—C16—C9—C849.7 (3)C9—C10—C11—C1212.1 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7···O10.982.953.145 (3)92
C5—H5···O20.932.432.748 (4)100
C10—H10B···Br0.972.833.202 (4)104
C9—H9···O1i0.982.993.893 (3)153
O2—H2···O1i0.822.122.824 (3)144
C4—H4···Brii0.932.933.808 (3)157
Symmetry codes: (i) x, y+1/2, z1/2; (ii) x1, y+1/2, z1/2.
 

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