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The title compound, C14H19BF2O3, can be described as a resonance hybrid. The entering BF2 moiety interacts with the C=O (oxo) groups of the parent compound, 5-(ethoxy­carbonyl)­adamantan-4-one, generating two conjugated double bonds in the six-membered di­fluoro­dioxoborane ring. In spite of the conjugation between the multiple bonds, the tetrahedral configuration of the B atom gives rise to a non-planar conformation of the six-membered ring, which assumes a state intermediate between the boat and sofa forms.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680302066X/wn6178sup1.cif
Contains datablocks 2, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680302066X/wn61782sup2.hkl
Contains datablock 2

CCDC reference: 225786

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.049
  • wR factor = 0.170
  • Data-to-parameter ratio = 32.7

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

Computing details top

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1992); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

ethyl 5-oxotricyclo[4.3.1.13,8]undecane-4-carboxylate difluoroborate top
Crystal data top
C14H19BF2O3Z = 2
Mr = 284.10F(000) = 300
Triclinic, P1Dx = 1.390 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71070 Å
a = 7.169 (1) ÅCell parameters from 25 reflections
b = 8.049 (1) Åθ = 18.0–18.9°
c = 11.858 (1) ŵ = 0.11 mm1
α = 89.06 (1)°T = 293 K
β = 83.36 (1)°Prism, colourless
γ = 87.22 (1)°0.50 × 0.50 × 0.45 mm
V = 678.82 (14) Å3
Data collection top
Enraf-Nonius CAD-4
diffractometer
3332 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.011
Graphite monochromatorθmax = 35.0°, θmin = 2.5°
ωθ scansh = 1111
Absorption correction: ψ scan
(North et al., 1968)
k = 612
Tmin = 0.936, Tmax = 0.951l = 1919
6462 measured reflections3 standard reflections every 60 min
5947 independent reflections intensity decay: 2%
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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.170H-atom parameters constrained
S = 1.10 w = 1/[σ2(Fo2) + (0.0914P)2]
where P = (Fo2 + 2Fc2)/3
5947 reflections(Δ/σ)max = 0.001
182 parametersΔρmax = 0.30 e Å3
179 restraintsΔρmin = 0.23 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
C10.71014 (18)0.36899 (15)0.07444 (10)0.0542 (3)
H10.70360.45130.01300.070*
C20.54699 (19)0.25402 (17)0.07187 (10)0.0555 (3)
H2A0.42980.31780.09140.072*
H2B0.54730.21410.00490.072*
C30.55396 (16)0.10398 (13)0.15272 (8)0.0445 (2)
H30.46840.02390.12850.058*
C40.48439 (13)0.14624 (12)0.27490 (8)0.0392 (2)
C50.56568 (14)0.26194 (12)0.33489 (8)0.0399 (2)
C60.73827 (15)0.34994 (14)0.28805 (10)0.0468 (2)
H60.77090.42170.34810.061*
C70.90558 (15)0.22488 (16)0.25932 (10)0.0508 (3)
H7A1.02120.28270.25930.066*
H7B0.90340.14050.31870.066*
C80.90812 (16)0.13906 (14)0.14523 (10)0.0497 (3)
H81.02860.07610.12980.065*
C90.89596 (18)0.26922 (16)0.05192 (10)0.0556 (3)
H9A0.90390.21550.02120.072*
H9B0.99970.34260.05050.072*
C100.70457 (18)0.46273 (14)0.18583 (12)0.0558 (3)
H10A0.58300.52110.20130.073*
H10B0.79940.54540.17700.073*
C110.75014 (18)0.01804 (13)0.14085 (9)0.0499 (3)
H11A0.77020.04040.06930.065*
H11B0.75640.06390.20140.065*
C120.35195 (14)0.04821 (13)0.33921 (9)0.0413 (2)
C130.17288 (19)0.19549 (17)0.36122 (11)0.0588 (3)
H13A0.05430.13820.38810.076*
H13B0.23280.23510.42650.076*
C140.1412 (2)0.33506 (18)0.28921 (14)0.0743 (4)
H14A0.08440.29400.22410.112*
H14B0.05930.41040.33160.112*
H14C0.25910.39230.26470.112*
O10.50478 (11)0.29875 (10)0.44054 (6)0.0504 (2)
O20.28850 (11)0.07668 (10)0.44265 (6)0.0503 (2)
O30.29505 (11)0.08253 (10)0.29158 (7)0.0496 (2)
B10.32616 (18)0.23966 (17)0.49515 (10)0.0470 (3)
F10.33825 (12)0.21058 (11)0.60759 (6)0.0662 (2)
F20.18140 (10)0.34935 (10)0.47812 (7)0.0663 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0600 (7)0.0482 (6)0.0526 (6)0.0072 (5)0.0006 (5)0.0160 (5)
C20.0583 (7)0.0632 (7)0.0458 (6)0.0079 (6)0.0088 (5)0.0089 (5)
C30.0515 (5)0.0464 (5)0.0355 (4)0.0153 (4)0.0007 (4)0.0035 (4)
C40.0374 (4)0.0411 (5)0.0384 (4)0.0091 (4)0.0017 (3)0.0026 (4)
C50.0384 (4)0.0396 (5)0.0408 (5)0.0059 (4)0.0022 (4)0.0046 (4)
C60.0422 (5)0.0457 (5)0.0520 (6)0.0140 (4)0.0034 (4)0.0094 (4)
C70.0383 (5)0.0618 (7)0.0520 (6)0.0073 (5)0.0020 (4)0.0018 (5)
C80.0442 (5)0.0507 (6)0.0505 (6)0.0032 (4)0.0085 (4)0.0019 (5)
C90.0569 (6)0.0583 (7)0.0479 (6)0.0100 (5)0.0119 (5)0.0076 (5)
C100.0537 (6)0.0393 (5)0.0720 (8)0.0088 (5)0.0054 (5)0.0030 (5)
C110.0634 (7)0.0408 (5)0.0415 (5)0.0021 (5)0.0106 (5)0.0022 (4)
C120.0357 (4)0.0453 (5)0.0426 (5)0.0090 (4)0.0001 (4)0.0030 (4)
C130.0581 (7)0.0613 (7)0.0572 (7)0.0305 (6)0.0041 (5)0.0026 (5)
C140.0890 (10)0.0561 (7)0.0762 (9)0.0328 (7)0.0107 (8)0.0061 (6)
O10.0505 (4)0.0546 (4)0.0450 (4)0.0135 (3)0.0062 (3)0.0144 (3)
O20.0483 (4)0.0548 (4)0.0454 (4)0.0154 (3)0.0104 (3)0.0044 (3)
O30.0490 (4)0.0518 (4)0.0483 (4)0.0233 (3)0.0020 (3)0.0046 (3)
B10.0470 (6)0.0532 (6)0.0383 (5)0.0047 (5)0.0070 (4)0.0044 (5)
F10.0804 (5)0.0777 (5)0.0390 (3)0.0118 (4)0.0024 (3)0.0004 (3)
F20.0560 (4)0.0665 (5)0.0725 (5)0.0075 (4)0.0047 (4)0.0010 (4)
Geometric parameters (Å, º) top
C1—C91.5205 (18)C8—C111.5351 (16)
C1—C101.5275 (19)C8—H80.9800
C1—C21.5295 (18)C9—H9A0.9700
C1—H10.9800C9—H9B0.9700
C2—C31.5321 (16)C10—H10A0.9700
C2—H2A0.9700C10—H10B0.9700
C2—H2B0.9700C11—H11A0.9700
C3—C41.5154 (13)C11—H11B0.9700
C3—C111.5295 (17)C12—O21.2784 (12)
C3—H30.9800C12—O31.3065 (12)
C4—C51.3723 (13)C13—O31.4701 (13)
C4—C121.4111 (13)C13—C141.4643 (19)
C5—O11.3118 (12)C13—H13A0.9700
C5—C61.5014 (13)C13—H13B0.9700
C6—C101.5370 (18)C14—H14A0.9600
C6—C71.5387 (16)C14—H14B0.9600
C6—H60.9800C14—H14C0.9600
C7—C81.5270 (17)O1—B11.4638 (14)
C7—H7A0.9700O2—B11.5104 (15)
C7—H7B0.9700B1—F21.3606 (16)
C8—C91.5181 (17)B1—F11.3618 (15)
C9—C1—C10109.56 (10)C8—C9—C1108.92 (9)
C9—C1—C2109.73 (10)C8—C9—H9A109.9
C10—C1—C2113.50 (10)C1—C9—H9A109.9
C9—C1—H1108.0C8—C9—H9B109.9
C10—C1—H1108.0C1—C9—H9B109.9
C2—C1—H1108.0H9A—C9—H9B108.3
C3—C2—C1113.98 (10)C1—C10—C6113.70 (9)
C3—C2—H2A108.8C1—C10—H10A108.8
C1—C2—H2A108.8C6—C10—H10A108.8
C3—C2—H2B108.8C1—C10—H10B108.8
C1—C2—H2B108.8C6—C10—H10B108.8
H2A—C2—H2B107.7H10A—C10—H10B107.7
C4—C3—C2113.16 (9)C3—C11—C8113.26 (9)
C4—C3—C11112.16 (9)C3—C11—H11A108.9
C2—C3—C11110.84 (9)C8—C11—H11A108.9
C4—C3—H3106.7C3—C11—H11B108.9
C2—C3—H3106.7C8—C11—H11B108.9
C11—C3—H3106.7H11A—C11—H11B107.7
C5—C4—C12115.55 (9)O2—C12—O3117.89 (9)
C5—C4—C3122.80 (8)O2—C12—C4123.87 (9)
C12—C4—C3120.83 (8)O3—C12—C4118.20 (9)
O1—C5—C4122.69 (9)O3—C13—C14107.16 (10)
O1—C5—C6114.10 (8)O3—C13—H13A110.3
C4—C5—C6123.11 (9)C14—C13—H13A110.3
C5—C6—C10112.51 (10)O3—C13—H13B110.3
C5—C6—C7110.81 (9)C14—C13—H13B110.3
C10—C6—C7111.58 (9)H13A—C13—H13B108.5
C5—C6—H6107.2C13—C14—H14A109.5
C10—C6—H6107.2C13—C14—H14B109.5
C7—C6—H6107.2H14A—C14—H14B109.5
C8—C7—C6114.51 (10)C13—C14—H14C109.5
C8—C7—H7A108.6H14A—C14—H14C109.5
C6—C7—H7A108.6H14B—C14—H14C109.5
C8—C7—H7B108.6C5—O1—B1121.26 (8)
C6—C7—H7B108.6C12—O2—B1119.47 (8)
H7A—C7—H7B107.6C12—O3—C13118.71 (9)
C9—C8—C7109.56 (10)F2—B1—F1111.94 (9)
C9—C8—C11108.92 (10)F2—B1—O1110.90 (10)
C7—C8—C11114.15 (9)F1—B1—O1109.72 (10)
C9—C8—H8108.0F2—B1—O2107.60 (10)
C7—C8—H8108.0F1—B1—O2107.63 (10)
C11—C8—H8108.0O1—B1—O2108.93 (8)
C9—C1—C2—C354.66 (13)C2—C1—C10—C667.50 (13)
C10—C1—C2—C368.29 (14)C5—C6—C10—C179.66 (12)
C1—C2—C3—C479.37 (13)C7—C6—C10—C145.60 (13)
C1—C2—C3—C1147.63 (13)C4—C3—C11—C878.53 (11)
C2—C3—C4—C559.52 (14)C2—C3—C11—C849.02 (12)
C11—C3—C4—C566.78 (13)C9—C8—C11—C357.55 (11)
C2—C3—C4—C12131.28 (11)C7—C8—C11—C365.23 (12)
C11—C3—C4—C12102.41 (11)C5—C4—C12—O29.69 (16)
C12—C4—C5—O110.53 (16)C3—C4—C12—O2179.63 (10)
C3—C4—C5—O1179.75 (10)C5—C4—C12—O3168.04 (10)
C12—C4—C5—C6165.77 (10)C3—C4—C12—O31.90 (16)
C3—C4—C5—C63.95 (17)C4—C5—O1—B110.67 (16)
O1—C5—C6—C10118.55 (10)C6—C5—O1—B1172.72 (10)
C4—C5—C6—C1064.86 (14)O3—C12—O2—B1170.48 (10)
O1—C5—C6—C7115.77 (10)C4—C12—O2—B111.78 (16)
C4—C5—C6—C760.83 (14)O2—C12—O3—C134.30 (16)
C5—C6—C7—C881.21 (12)C4—C12—O3—C13173.57 (10)
C10—C6—C7—C845.00 (13)C14—C13—O3—C12176.39 (12)
C6—C7—C8—C953.94 (12)C5—O1—B1—F288.99 (12)
C6—C7—C8—C1168.50 (13)C5—O1—B1—F1146.84 (10)
C7—C8—C9—C162.40 (12)C5—O1—B1—O229.25 (14)
C11—C8—C9—C163.10 (12)C12—O2—B1—F290.69 (11)
C10—C1—C9—C863.46 (12)C12—O2—B1—F1148.50 (10)
C2—C1—C9—C861.79 (13)C12—O2—B1—O129.60 (14)
C9—C1—C10—C655.54 (12)
 

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