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The title compound, C11H9O, was prepared in two steps starting from indene. There are two crystallographically independent mol­ecules in the asymmetric unit. Each is essentially planar, with only the atoms of the cyclo­propanone group lying out of the mol­ecular plane.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806017739/sg2026sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806017739/sg2026Isup2.hkl
Contains datablock I

CCDC reference: 610886

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.051
  • wR factor = 0.138
  • Data-to-parameter ratio = 12.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.96 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 8
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: COLLECT (Nonius, 2002); cell refinement: COLLECT; data reduction: COLLECT; program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1990); software used to prepare material for publication: SHELXTL.

Spiro[cyclopropane-1,1'-1H-inden]-2'(3'H)-one' top
Crystal data top
C11H9OF(000) = 332
Mr = 157.18Dx = 1.247 Mg m3
Monoclinic, P21/mMo Kα radiation, λ = 0.71073 Å
a = 8.941 (1) ÅCell parameters from 225 reflections
b = 6.996 (1) Åθ = 3.1–18.7°
c = 13.491 (2) ŵ = 0.08 mm1
β = 97.34 (1)°T = 173 K
V = 837.0 (2) Å3Prism, colorless
Z = 40.30 × 0.30 × 0.25 mm
Data collection top
Nonius KappaCCD
diffractometer
2000 independent reflections
Radiation source: fine-focus sealed tube1511 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
φ? ω? scansθmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 117
Tmin = 0.977, Tmax = 0.981k = 85
4074 measured reflectionsl = 1716
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)] = 0.051H-atom parameters constrained
wR(F2) = 0.138 w = 1/[σ2(Fo2) + (0.0611P)2 + 0.4406P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
2000 reflectionsΔρmax = 0.33 e Å3
158 parametersΔρmin = 0.26 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.061 (14)
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*/UeqOcc. (<1)
O1A0.1066 (2)0.25000.44049 (14)0.0424 (5)
C2A0.2371 (3)0.25000.47846 (17)0.0268 (5)
C3A0.2893 (3)0.25000.58846 (16)0.0237 (5)
C4A0.4571 (3)0.25000.60005 (16)0.0230 (5)
C5A0.5600 (3)0.25000.68629 (18)0.0305 (6)
H5AA0.52620.25000.75030.037*
C6A0.7131 (3)0.25000.6776 (2)0.0378 (6)
H6AA0.78440.25000.73620.045*
C7A0.7635 (3)0.25000.5841 (2)0.0401 (7)
H7AA0.86860.25000.57930.048*
C8A0.6610 (3)0.25000.4981 (2)0.0334 (6)
H8AA0.69560.25000.43440.040*
C9A0.5072 (3)0.25000.50523 (17)0.0244 (5)
C10A0.3759 (3)0.25000.42331 (17)0.0276 (5)
H10A0.374 (4)0.370 (5)0.378 (3)0.033*0.50
C11A0.1948 (2)0.1438 (3)0.65731 (14)0.0342 (4)
H11A0.107 (2)0.077 (3)0.6228 (14)0.041*
H12A0.258 (2)0.082 (3)0.7151 (15)0.041*
O1B0.3531 (2)0.25000.09557 (14)0.0415 (5)
C2B0.2469 (3)0.25000.04732 (17)0.0263 (5)
C3B0.2597 (3)0.25000.06467 (17)0.0234 (5)
C4B0.1034 (3)0.25000.09056 (16)0.0234 (5)
C5B0.0554 (3)0.25000.18489 (19)0.0312 (6)
H5BA0.12670.25000.24350.037*
C6B0.0969 (3)0.25000.1918 (2)0.0419 (7)
H6BA0.13110.25000.25570.050*
C7B0.2006 (3)0.25000.1063 (3)0.0469 (8)
H7BA0.30530.25000.11230.056*
C8B0.1539 (3)0.25000.0111 (2)0.0378 (7)
H8BA0.22590.25000.04710.045*
C9B0.0003 (3)0.25000.00338 (18)0.0250 (5)
C10B0.0800 (3)0.25000.08879 (17)0.0271 (5)
H10C0.061 (4)0.132 (5)0.135 (3)0.032*0.50
C11B0.3903 (2)0.1436 (3)0.12372 (14)0.0338 (4)
H11B0.461 (2)0.080 (3)0.0819 (14)0.041*
H12B0.364 (2)0.081 (3)0.1839 (14)0.041*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0310 (10)0.0545 (13)0.0391 (10)0.0000.0050 (8)0.000
C2A0.0308 (13)0.0217 (11)0.0270 (11)0.0000.0001 (10)0.000
C3A0.0261 (11)0.0217 (11)0.0239 (11)0.0000.0050 (9)0.000
C4A0.0271 (12)0.0164 (11)0.0254 (11)0.0000.0027 (9)0.000
C5A0.0378 (14)0.0221 (12)0.0298 (12)0.0000.0029 (10)0.000
C6A0.0324 (14)0.0276 (13)0.0493 (16)0.0000.0102 (12)0.000
C7A0.0261 (13)0.0285 (14)0.0649 (19)0.0000.0023 (13)0.000
C8A0.0350 (14)0.0223 (12)0.0459 (15)0.0000.0171 (12)0.000
C9A0.0294 (12)0.0174 (11)0.0264 (11)0.0000.0043 (9)0.000
C10A0.0363 (13)0.0255 (12)0.0215 (11)0.0000.0056 (10)0.000
C11A0.0342 (10)0.0353 (10)0.0349 (9)0.0038 (8)0.0120 (8)0.0038 (8)
O1B0.0411 (11)0.0495 (12)0.0381 (10)0.0000.0211 (9)0.000
C2B0.0305 (12)0.0232 (11)0.0265 (12)0.0000.0082 (10)0.000
C3B0.0222 (11)0.0228 (11)0.0252 (11)0.0000.0026 (9)0.000
C4B0.0267 (12)0.0164 (11)0.0275 (11)0.0000.0053 (9)0.000
C5B0.0422 (14)0.0220 (12)0.0317 (12)0.0000.0139 (11)0.000
C6B0.0518 (18)0.0220 (13)0.0587 (18)0.0000.0334 (15)0.000
C7B0.0297 (14)0.0239 (14)0.093 (2)0.0000.0314 (16)0.000
C8B0.0228 (12)0.0227 (13)0.0663 (18)0.0000.0001 (12)0.000
C9B0.0245 (11)0.0148 (10)0.0348 (12)0.0000.0009 (9)0.000
C10B0.0316 (12)0.0244 (12)0.0238 (11)0.0000.0018 (9)0.000
C11B0.0288 (9)0.0326 (10)0.0385 (9)0.0040 (7)0.0022 (7)0.0026 (8)
Geometric parameters (Å, º) top
O1A—C2A1.213 (3)O1B—C2B1.218 (3)
C2A—C3A1.498 (3)C2B—C3B1.500 (3)
C2A—C10A1.527 (3)C2B—C10B1.525 (3)
C3A—C4A1.489 (3)C3B—C4B1.483 (3)
C3A—C11Ai1.526 (2)C3B—C11Bi1.521 (3)
C3A—C11A1.526 (2)C3B—C11B1.521 (3)
C4A—C5A1.388 (3)C4B—C5B1.394 (3)
C4A—C9A1.408 (3)C4B—C9B1.399 (3)
C5A—C6A1.389 (4)C5B—C6B1.377 (4)
C5A—H5AA0.9500C5B—H5BA0.9500
C6A—C7A1.394 (4)C6B—C7B1.385 (5)
C6A—H6AA0.9500C6B—H6BA0.9500
C7A—C8A1.383 (4)C7B—C8B1.400 (4)
C7A—H7AA0.9500C7B—H7BA0.9500
C8A—C9A1.391 (3)C8B—C9B1.396 (3)
C8A—H8AA0.9500C8B—H8BA0.9500
C9A—C10A1.506 (3)C9B—C10B1.510 (3)
C10A—H10A1.04 (4)C10B—H10C1.04 (4)
C11A—C11Ai1.486 (4)C11B—C11Bi1.488 (4)
C11A—H11A0.98 (2)C11B—H11B1.00 (2)
C11A—H12A1.00 (2)C11B—H12B0.98 (2)
O1A—C2A—C3A125.4 (2)O1B—C2B—C3B125.0 (2)
O1A—C2A—C10A126.3 (2)O1B—C2B—C10B126.7 (2)
C3A—C2A—C10A108.25 (19)C3B—C2B—C10B108.36 (19)
C4A—C3A—C2A106.65 (18)C4B—C3B—C2B106.49 (19)
C4A—C3A—C11Ai124.39 (16)C4B—C3B—C11Bi124.04 (17)
C2A—C3A—C11Ai118.45 (17)C2B—C3B—C11Bi118.84 (17)
C4A—C3A—C11A124.39 (16)C4B—C3B—C11B124.04 (17)
C2A—C3A—C11A118.45 (17)C2B—C3B—C11B118.84 (17)
C11Ai—C3A—C11A58.28 (16)C11Bi—C3B—C11B58.59 (16)
C5A—C4A—C9A120.5 (2)C5B—C4B—C9B121.4 (2)
C5A—C4A—C3A129.8 (2)C5B—C4B—C3B128.6 (2)
C9A—C4A—C3A109.74 (19)C9B—C4B—C3B109.99 (19)
C4A—C5A—C6A119.0 (2)C6B—C5B—C4B119.0 (3)
C4A—C5A—H5AA120.5C6B—C5B—H5BA120.5
C6A—C5A—H5AA120.5C4B—C5B—H5BA120.5
C5A—C6A—C7A120.8 (2)C5B—C6B—C7B120.4 (3)
C5A—C6A—H6AA119.6C5B—C6B—H6BA119.8
C7A—C6A—H6AA119.6C7B—C6B—H6BA119.8
C8A—C7A—C6A120.2 (2)C6B—C7B—C8B121.2 (2)
C8A—C7A—H7AA119.9C6B—C7B—H7BA119.4
C6A—C7A—H7AA119.9C8B—C7B—H7BA119.4
C7A—C8A—C9A119.8 (2)C9B—C8B—C7B118.8 (3)
C7A—C8A—H8AA120.1C9B—C8B—H8BA120.6
C9A—C8A—H8AA120.1C7B—C8B—H8BA120.6
C8A—C9A—C4A119.7 (2)C8B—C9B—C4B119.2 (2)
C8A—C9A—C10A129.4 (2)C8B—C9B—C10B129.5 (2)
C4A—C9A—C10A111.0 (2)C4B—C9B—C10B111.3 (2)
C9A—C10A—C2A104.38 (18)C9B—C10B—C2B103.91 (18)
C9A—C10A—H10A113 (2)C9B—C10B—H10C116 (2)
C2A—C10A—H10A109 (2)C2B—C10B—H10C107 (2)
C11Ai—C11A—C3A60.86 (8)C11Bi—C11B—C3B60.70 (8)
C11Ai—C11A—H11A118.3 (12)C11Bi—C11B—H11B116.5 (12)
C3A—C11A—H11A114.5 (11)C3B—C11B—H11B114.8 (11)
C11Ai—C11A—H12A115.6 (12)C11Bi—C11B—H12B116.7 (12)
C3A—C11A—H12A112.7 (11)C3B—C11B—H12B113.9 (11)
H11A—C11A—H12A120.3 (17)H11B—C11B—H12B120.1 (17)
Symmetry code: (i) x, y+1/2, z.
 

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