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The title mol­ecule, C26H34O4, shows a very short repulsive intramolecular C-H...H-C contact, with an H...H distance of only 1.71 Å. The flap angle [varphi] of the bi­cyclo­[1.1.0]­butane group is widened to 131.23 (8)°. Both methyl­ene C atoms show tilt angles of 6.1°. Bond lengths in the fused cyclo­propane rings range from 1.501 (1) to 1.542 (1) Å and are influenced by [pi] interactions with the carboxyl­ate substituents.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S010827010100004X/sk1443sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010827010100004X/sk1443Isup2.hkl
Contains datablock I

CCDC reference: 163919

Computing details top

Data collection: SMART (Siemens, 1995); cell refinement: SMART; data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Sheldrick, 1996); software used to prepare material for publication: CIF in SHELXL97.

Dimethyl dispiro[tricyclo[3.3.1.13,7]decan-1,2'-bicyclo[1.1.0]butan-4',1"- tricyclo[3.3.1.13,7]decane]-1',3'-dicarboxylate top
Crystal data top
C26H34O4Z = 2
Mr = 410.53F(000) = 444
Triclinic, P1Dx = 1.315 Mg m3
a = 9.710 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.3412 (12) ÅCell parameters from 154 reflections
c = 11.051 (2) Åθ = 3–23°
α = 89.442 (11)°µ = 0.09 mm1
β = 82.317 (14)°T = 143 K
γ = 70.628 (8)°Block, colorless
V = 1036.7 (3) Å30.48 × 0.40 × 0.28 mm
Data collection top
Siemens SMART
diffractometer
5993 independent reflections
Radiation source: normal-focus sealed tube5005 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.039
ω scansθmax = 31.0°, θmin = 1.9°
Absorption correction: numerical
using 7 indexed faces (SHELXTL; Sheldrick, 1996)
h = 1313
Tmin = 0.952, Tmax = 0.979k = 1514
18851 measured reflectionsl = 1415
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040H-atom parameters constrained
wR(F2) = 0.108 w = 1/[σ2(Fo2) + (0.05P)2 + 0.3P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
5993 reflectionsΔρmax = 0.37 e Å3
274 parametersΔρmin = 0.22 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.010 (2)
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
O10.42055 (8)0.32625 (8)0.57659 (7)0.02072 (16)
O20.25334 (9)0.24662 (10)0.51236 (8)0.0295 (2)
O30.37319 (11)0.09580 (9)0.12022 (8)0.0303 (2)
O40.42088 (11)0.00529 (9)0.30046 (9)0.0345 (2)
C10.35946 (12)0.31470 (12)0.70090 (10)0.0227 (2)
H1A0.41430.34410.75700.036*
H1B0.36690.21910.71520.036*
H1C0.25570.37310.71500.036*
C20.35698 (10)0.28582 (10)0.49006 (9)0.01687 (19)
C30.43031 (10)0.30462 (10)0.36752 (9)0.01465 (18)
C40.45481 (10)0.22145 (10)0.24934 (9)0.01527 (18)
C50.41527 (11)0.09617 (10)0.23112 (10)0.0188 (2)
C60.32966 (17)0.01992 (14)0.09111 (13)0.0390 (3)
H6A0.27670.00010.01990.062*
H6B0.26520.03680.16110.062*
H6C0.41760.10140.07260.062*
C70.35160 (10)0.36726 (10)0.25817 (9)0.01417 (18)
C80.37632 (10)0.48833 (10)0.18828 (9)0.01560 (18)
H80.48380.47660.17650.019*
C90.28983 (12)0.62223 (10)0.26257 (10)0.0203 (2)
H9A0.32350.61830.34360.024*
H9B0.30810.70070.21970.024*
C100.12491 (12)0.64259 (11)0.27870 (10)0.0212 (2)
H100.06890.72960.32720.025*
C110.07358 (11)0.64998 (11)0.15280 (10)0.0230 (2)
H11A0.03350.66520.16250.028*
H11B0.09160.72790.10870.028*
C120.15783 (11)0.51578 (11)0.07917 (9)0.0204 (2)
H120.12370.52000.00270.025*
C130.13139 (11)0.39529 (11)0.14811 (10)0.0207 (2)
H13A0.18420.30890.09960.025*
H13B0.02480.40780.15970.025*
C140.18625 (10)0.38593 (10)0.27338 (9)0.01628 (19)
H140.16830.30710.31780.020*
C150.10014 (11)0.52073 (11)0.34696 (9)0.0199 (2)
H15A0.00630.53270.35950.024*
H15B0.13340.51690.42820.024*
C160.32288 (11)0.49341 (11)0.06308 (9)0.0192 (2)
H16A0.34290.56900.01650.023*
H16B0.37730.40630.01610.023*
C170.58552 (10)0.22727 (10)0.31183 (9)0.01446 (18)
C180.69998 (10)0.29134 (10)0.25623 (9)0.01571 (18)
H180.64900.38060.22000.019*
C190.78388 (11)0.31636 (10)0.35730 (10)0.01844 (19)
H19A0.85430.36230.32310.022*
H19B0.71340.37740.42270.022*
C200.86764 (11)0.18011 (11)0.41104 (10)0.0199 (2)
H200.92420.19720.47480.024*
C210.97368 (11)0.08379 (11)0.30920 (10)0.0210 (2)
H21A1.04620.12590.27150.025*
H21B1.02820.00400.34390.025*
C220.88707 (11)0.05673 (10)0.21186 (10)0.0189 (2)
H220.95630.00760.14650.023*
C230.77315 (11)0.00646 (10)0.27077 (10)0.0187 (2)
H23A0.82410.09480.30650.022*
H23B0.71770.02470.20780.022*
C240.66555 (10)0.09231 (10)0.37140 (9)0.01657 (19)
H240.59180.05040.40950.020*
C250.75475 (11)0.11592 (11)0.46857 (9)0.0197 (2)
H25A0.68750.17750.53530.024*
H25B0.80600.02740.50390.024*
C260.80737 (11)0.19318 (10)0.15616 (9)0.01813 (19)
H26A0.88030.23470.11820.022*
H26B0.75260.17680.09180.022*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0228 (4)0.0253 (4)0.0160 (3)0.0119 (3)0.0008 (3)0.0013 (3)
O20.0273 (4)0.0459 (5)0.0245 (4)0.0233 (4)0.0077 (3)0.0145 (4)
O30.0477 (5)0.0270 (4)0.0242 (4)0.0224 (4)0.0067 (4)0.0036 (3)
O40.0429 (5)0.0250 (4)0.0464 (5)0.0212 (4)0.0192 (4)0.0140 (4)
C10.0262 (5)0.0254 (5)0.0167 (5)0.0103 (4)0.0008 (4)0.0012 (4)
C20.0157 (4)0.0148 (4)0.0193 (5)0.0036 (3)0.0038 (3)0.0053 (3)
C30.0140 (4)0.0141 (4)0.0165 (4)0.0051 (3)0.0035 (3)0.0033 (3)
C40.0149 (4)0.0139 (4)0.0178 (4)0.0054 (3)0.0033 (3)0.0021 (3)
C50.0145 (4)0.0157 (4)0.0261 (5)0.0056 (3)0.0016 (4)0.0002 (4)
C60.0529 (8)0.0343 (7)0.0393 (7)0.0273 (6)0.0047 (6)0.0125 (6)
C70.0132 (4)0.0146 (4)0.0154 (4)0.0050 (3)0.0036 (3)0.0023 (3)
C80.0137 (4)0.0167 (4)0.0169 (4)0.0052 (3)0.0035 (3)0.0049 (3)
C90.0242 (5)0.0160 (5)0.0219 (5)0.0072 (4)0.0057 (4)0.0032 (4)
C100.0211 (5)0.0173 (5)0.0204 (5)0.0009 (4)0.0012 (4)0.0020 (4)
C110.0166 (4)0.0244 (5)0.0239 (5)0.0012 (4)0.0036 (4)0.0091 (4)
C120.0173 (4)0.0285 (5)0.0161 (5)0.0070 (4)0.0060 (4)0.0058 (4)
C130.0183 (4)0.0263 (5)0.0204 (5)0.0096 (4)0.0077 (4)0.0033 (4)
C140.0133 (4)0.0190 (5)0.0176 (4)0.0063 (3)0.0034 (3)0.0042 (4)
C150.0163 (4)0.0233 (5)0.0167 (5)0.0029 (4)0.0004 (4)0.0031 (4)
C160.0168 (4)0.0243 (5)0.0152 (4)0.0052 (4)0.0021 (3)0.0046 (4)
C170.0134 (4)0.0139 (4)0.0170 (4)0.0052 (3)0.0036 (3)0.0030 (3)
C180.0139 (4)0.0152 (4)0.0192 (5)0.0059 (3)0.0038 (3)0.0044 (3)
C190.0172 (4)0.0179 (5)0.0217 (5)0.0071 (4)0.0042 (4)0.0001 (4)
C200.0183 (4)0.0226 (5)0.0204 (5)0.0072 (4)0.0078 (4)0.0026 (4)
C210.0144 (4)0.0212 (5)0.0260 (5)0.0033 (4)0.0050 (4)0.0039 (4)
C220.0169 (4)0.0177 (5)0.0203 (5)0.0040 (4)0.0012 (4)0.0002 (4)
C230.0188 (4)0.0140 (4)0.0230 (5)0.0048 (4)0.0040 (4)0.0021 (4)
C240.0156 (4)0.0146 (4)0.0193 (5)0.0042 (3)0.0040 (3)0.0050 (3)
C250.0191 (4)0.0213 (5)0.0176 (5)0.0046 (4)0.0050 (4)0.0042 (4)
C260.0177 (4)0.0208 (5)0.0173 (5)0.0082 (4)0.0026 (4)0.0029 (4)
Geometric parameters (Å, º) top
O1—C21.3442 (13)C10—C151.5326 (15)
O1—C11.4420 (13)C11—C121.5324 (16)
O2—C21.2001 (13)C12—C161.5272 (14)
O3—C51.3431 (14)C12—C131.5299 (15)
O3—C61.4470 (14)C13—C141.5394 (14)
O4—C51.1986 (13)C14—C151.5397 (15)
C2—C31.4857 (14)C17—C181.5329 (13)
C3—C171.5006 (13)C17—C241.5443 (13)
C3—C41.5182 (14)C18—C261.5337 (14)
C3—C71.5387 (13)C18—C191.5384 (14)
C4—C51.4907 (13)C19—C201.5336 (14)
C4—C71.5039 (13)C20—C251.5279 (15)
C4—C171.5417 (13)C20—C211.5332 (15)
C7—C81.5338 (13)C21—C221.5319 (15)
C7—C141.5382 (13)C22—C231.5340 (14)
C8—C161.5360 (14)C22—C261.5346 (14)
C8—C91.5372 (14)C23—C241.5412 (14)
C9—C101.5301 (15)C24—C251.5353 (14)
C10—C111.5323 (15)
C2—O1—C1115.45 (8)C12—C11—C10109.63 (8)
C5—O3—C6115.46 (10)C16—C12—C13108.24 (8)
O2—C2—O1123.42 (10)C16—C12—C11109.64 (9)
O2—C2—C3127.21 (10)C13—C12—C11109.70 (9)
O1—C2—C3109.30 (8)C12—C13—C14110.27 (8)
C2—C3—C17126.86 (8)C7—C14—C13110.73 (8)
C2—C3—C4129.16 (8)C7—C14—C15108.79 (8)
C17—C3—C461.42 (6)C13—C14—C15108.19 (8)
C2—C3—C7125.72 (8)C10—C15—C14110.18 (8)
C17—C3—C7104.41 (8)C12—C16—C8110.23 (8)
C4—C3—C758.93 (6)C3—C17—C18125.79 (8)
C5—C4—C7126.45 (8)C3—C17—C459.85 (6)
C5—C4—C3127.32 (8)C18—C17—C4124.24 (8)
C7—C4—C361.21 (6)C3—C17—C24116.95 (8)
C5—C4—C17125.54 (8)C18—C17—C24108.80 (8)
C7—C4—C17104.10 (7)C4—C17—C24113.76 (8)
C3—C4—C1758.73 (6)C17—C18—C26109.11 (8)
O4—C5—O3122.72 (10)C17—C18—C19109.05 (8)
O4—C5—C4127.59 (10)C26—C18—C19110.13 (8)
O3—C5—C4109.68 (9)C20—C19—C18110.41 (8)
C4—C7—C8126.51 (8)C25—C20—C21109.81 (9)
C4—C7—C14115.84 (8)C25—C20—C19108.00 (8)
C8—C7—C14108.62 (7)C21—C20—C19109.67 (8)
C4—C7—C359.85 (6)C22—C21—C20109.86 (8)
C8—C7—C3123.88 (8)C21—C22—C23109.61 (9)
C14—C7—C3114.88 (8)C21—C22—C26108.96 (8)
C7—C8—C16109.60 (8)C23—C22—C26109.35 (8)
C7—C8—C9109.12 (8)C22—C23—C24109.99 (8)
C16—C8—C9109.81 (8)C25—C24—C23108.22 (8)
C10—C9—C8109.81 (8)C25—C24—C17111.68 (8)
C9—C10—C11109.27 (9)C23—C24—C17108.20 (8)
C9—C10—C15108.37 (8)C20—C25—C24109.88 (8)
C11—C10—C15110.22 (9)C18—C26—C22109.62 (8)
C1—O1—C2—O22.33 (14)C3—C7—C14—C1582.83 (10)
C1—O1—C2—C3179.55 (8)C12—C13—C14—C758.93 (11)
O2—C2—C3—C17115.47 (12)C12—C13—C14—C1560.20 (10)
O1—C2—C3—C1767.45 (12)C9—C10—C15—C1460.14 (11)
O2—C2—C3—C434.71 (16)C11—C10—C15—C1459.39 (11)
O1—C2—C3—C4148.21 (9)C7—C14—C15—C1060.88 (10)
O2—C2—C3—C741.76 (16)C13—C14—C15—C1059.47 (10)
O1—C2—C3—C7135.33 (9)C13—C12—C16—C860.88 (11)
C2—C3—C4—C52.84 (16)C11—C12—C16—C858.76 (11)
C17—C3—C4—C5113.09 (11)C7—C8—C16—C1261.76 (11)
C7—C3—C4—C5115.69 (11)C9—C8—C16—C1258.09 (11)
C2—C3—C4—C7112.85 (11)C2—C3—C17—C18128.09 (11)
C17—C3—C4—C7131.22 (8)C4—C3—C17—C18112.55 (10)
C2—C3—C4—C17115.93 (11)C7—C3—C17—C1870.85 (11)
C7—C3—C4—C17131.22 (8)C2—C3—C17—C4119.37 (11)
C6—O3—C5—O42.11 (16)C7—C3—C17—C441.70 (7)
C6—O3—C5—C4179.21 (10)C2—C3—C17—C2416.22 (14)
C7—C4—C5—O4115.56 (13)C4—C3—C17—C24103.15 (9)
C3—C4—C5—O436.50 (17)C7—C3—C17—C24144.84 (8)
C17—C4—C5—O438.57 (17)C5—C4—C17—C3115.96 (11)
C7—C4—C5—O365.84 (13)C7—C4—C17—C342.82 (7)
C3—C4—C5—O3144.90 (10)C5—C4—C17—C18129.03 (10)
C17—C4—C5—O3140.03 (10)C7—C4—C17—C1872.19 (11)
C5—C4—C7—C8131.14 (11)C3—C4—C17—C18115.01 (10)
C3—C4—C7—C8111.85 (10)C5—C4—C17—C247.48 (13)
C17—C4—C7—C870.34 (11)C7—C4—C17—C24151.30 (8)
C5—C4—C7—C1411.97 (14)C3—C4—C17—C24108.48 (9)
C3—C4—C7—C14105.03 (9)C3—C17—C18—C26151.18 (9)
C17—C4—C7—C14146.55 (8)C4—C17—C18—C2676.14 (11)
C5—C4—C7—C3117.00 (11)C24—C17—C18—C2662.15 (10)
C17—C4—C7—C341.52 (7)C3—C17—C18—C1988.50 (11)
C2—C3—C7—C4118.35 (11)C4—C17—C18—C19163.53 (8)
C17—C3—C7—C443.00 (7)C24—C17—C18—C1958.18 (10)
C2—C3—C7—C8125.63 (10)C17—C18—C19—C2062.27 (10)
C17—C3—C7—C873.03 (11)C26—C18—C19—C2057.43 (10)
C4—C3—C7—C8116.02 (10)C18—C19—C20—C2562.07 (11)
C2—C3—C7—C1411.71 (13)C18—C19—C20—C2157.57 (10)
C17—C3—C7—C14149.63 (8)C25—C20—C21—C2258.85 (11)
C4—C3—C7—C14106.64 (9)C19—C20—C21—C2259.68 (11)
C4—C7—C8—C1686.22 (11)C20—C21—C22—C2358.47 (11)
C14—C7—C8—C1659.03 (10)C20—C21—C22—C2661.16 (11)
C3—C7—C8—C16161.41 (8)C21—C22—C23—C2459.82 (10)
C4—C7—C8—C9153.50 (9)C26—C22—C23—C2459.57 (11)
C14—C7—C8—C961.25 (10)C22—C23—C24—C2560.47 (10)
C3—C7—C8—C978.31 (11)C22—C23—C24—C1760.71 (10)
C7—C8—C9—C1061.50 (10)C3—C17—C24—C2592.73 (10)
C16—C8—C9—C1058.65 (10)C18—C17—C24—C2557.28 (10)
C8—C9—C10—C1159.94 (11)C4—C17—C24—C25159.67 (8)
C8—C9—C10—C1560.19 (11)C3—C17—C24—C23148.27 (8)
C9—C10—C11—C1260.61 (11)C18—C17—C24—C2361.72 (10)
C15—C10—C11—C1258.38 (11)C4—C17—C24—C2381.33 (10)
C10—C11—C12—C1660.01 (11)C21—C20—C25—C2460.37 (10)
C10—C11—C12—C1358.73 (11)C19—C20—C25—C2459.18 (11)
C16—C12—C13—C1459.16 (11)C23—C24—C25—C2060.66 (10)
C11—C12—C13—C1460.44 (11)C17—C24—C25—C2058.33 (11)
C4—C7—C14—C1391.39 (10)C17—C18—C26—C2260.80 (10)
C8—C7—C14—C1358.01 (10)C19—C18—C26—C2258.86 (10)
C3—C7—C14—C13158.41 (8)C21—C22—C26—C1860.59 (10)
C4—C7—C14—C15149.84 (8)C23—C22—C26—C1859.20 (10)
C8—C7—C14—C1560.76 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1B···O4i0.982.533.288 (2)134
C13—H13A···O30.992.393.194 (2)138
C14—H14···O21.002.413.039 (2)120
C23—H23A···O2i0.992.713.482 (2)135
C24—H24···O41.002.343.000 (2)122
C25—H25A···O10.992.523.320 (2)138
Symmetry code: (i) x+1, y, z+1.
 

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