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3-(4-Fluoro-benzyl-idene)-1,5-dioxa-spiro-[5.5]undecane-2,4-dione.
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PMID:  21522968     Owner:  NLM     Status:  PubMed-not-MEDLINE    
Abstract/OtherAbstract:
In the title mol-ecule, C(16)H(15)FO(4), the fused 1,3-dioxane and cyclo-hexane rings exhibit a bath and a chair conformation, respectively. In the crystal, weak inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into centrosymmetric dimers.
Authors:
Wu-Lan Zeng
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Publication Detail:
Type:  Journal Article     Date:  2011-01-08
Journal Detail:
Title:  Acta crystallographica. Section E, Structure reports online     Volume:  67     ISSN:  1600-5368     ISO Abbreviation:  Acta Crystallogr Sect E Struct Rep Online     Publication Date:  2011  
Date Detail:
Created Date:  2011-04-27     Completed Date:  2011-07-14     Revised Date:  2013-03-28    
Medline Journal Info:
Nlm Unique ID:  101089178     Medline TA:  Acta Crystallogr Sect E Struct Rep Online     Country:  England    
Other Details:
Languages:  eng     Pagination:  o276     Citation Subset:  -    
Affiliation:
MicroScale Science Institute, Department of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China.
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Journal Information
Journal ID (nlm-ta): Acta Crystallogr Sect E Struct Rep Online
Journal ID (publisher-id): Acta Cryst. E
ISSN: 1600-5368
Publisher: International Union of Crystallography
Article Information
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A full version of this article is available from Crystallography Journals Online.© Wu-Lan Zeng 2011
open-access:
Received Day: 21 Month: 12 Year: 2010
Accepted Day: 27 Month: 12 Year: 2010
collection publication date: Day: 01 Month: 2 Year: 2011
Electronic publication date: Day: 08 Month: 1 Year: 2011
pmc-release publication date: Day: 08 Month: 1 Year: 2011
Volume: 67 Issue: Pt 2
First Page: o276 Last Page: o276
ID: 3051599
PubMed Id: 21522968
Publisher Id: cv5023
DOI: 10.1107/S1600536810054395
Coden: ACSEBH
Publisher Item Identifier: S1600536810054395

3-(4-Fluoro­benzyl­idene)-1,5-dioxa­spiro­[5.5]undecane-2,4-dione Alternate Title:C16H15FO4
Wu-Lan Zenga*
aMicroScale Science Institute, Department of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People’s Republic of China
Correspondence: Correspondence e-mail: wulanzeng@163.com

Related literature

For related structures, see: Zeng & Jian (2009); Zeng et al. (2009). For applications of spiro compounds, see: Jiang et al. (1998); Lian et al. (2008); Wei et al. (2008).[Chemical Structure ID: scheme1]


Experimental
Crystal data

  • C16H15FO4
  • Mr = 290.28
  • Triclinic,
  • a = 5.6690 (11) Å
  • b = 10.130 (2) Å
  • c = 12.160 (2) Å
  • α = 100.68 (3)°
  • β = 90.73 (3)°
  • γ = 91.20 (3)°
  • V = 686.0 (2) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.11 mm−1
  • T = 293 K
  • 0.25 × 0.18 × 0.12 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • 6753 measured reflections
  • 3124 independent reflections
  • 2481 reflections with I > 2σ(I)
  • Rint = 0.029

Refinement

  • R[F2 > 2σ(F2)] = 0.040
  • wR(F2) = 0.127
  • S = 1.11
  • 3124 reflections
  • 190 parameters
  • H-atom parameters constrained
  • Δρmax = 0.22 e Å−3
  • Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.


Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810054395/cv5023sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810054395/cv5023Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report


Notes

fnu1Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV5023).

supplementary crystallographic information
Comment

Spiro compounds are widely used in medicine, catalysis and optical material (Lian et al., 2008; Jiang et al., 1998; Wei et al., 2008). As a part of our search for new spiro compounds with potentially high bioactivity (Zeng et al., 2009a,b), the title compound, (I), has been synthesized. Herewith we present its crystal structure.

In (I) (Fig. 1), the 1,3-dioxane ring is in a bath conformation with atom C4 atom common to the cyclohexane forming the flap. The cyclohexane ring exists in a distorted chair comformation. In the crystal structure, weak intermolecular C—H···O hydrogen bonds (Table 1) link the molecules into centrosymmetric dimers.

Experimental

The mixture of malonic acid (6.24 g, 0.06 mol) and acetic anhydride(9 ml) in strong sulfuric acid (0.25 ml) was stirred with water at 303K, After dissolving, cyclohexanone (5.88 g, 0.06 mol) was added dropwise into solution for 1 h. The reaction was allowed to proceed for 3 h. The mixture was cooled and filtered, and then an ethanol solution of 4-fluorobenzaldehyde (7.44g,0.06 mol) was added. The solution was then filtered and concentrated. Single crystals were obtained by evaporation of an petroleum ether-ethylacetate (3:1 v/v) solution of (I) at room temperature over a period of one week.

Refinement

The H atoms were placed in calculated positions (C—H = 0.93–0.97 Å), and refined as riding, with Uiso(H) = 1.2Ueq(C).

Figures
Crystal data
Data collection
Refinement
Special details
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
Atomic displacement parameters (Å2)
Geometric parameters (Å, °)
Hydrogen-bond geometry (Å, °)

Symmetry codes: (i) −x+1, −y, −z+2.


References
Bruker (1997). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
Jiang, Y. Z., Xue, S., Li, Z., Deng, J. G., Mi, A. Q. & Albert, S. C. C. (1998). Tetrahedron, 9, 3185–3189.
Lian, Y., Guo, J. J., Liu, X. M. & Wei, R. B. (2008). Chem. Res. Chin. Univ.24, 441–444.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Wei, R. B., Liu, B., Liu, Y., Guo, J. J. & Zhang, D. W. (2008). Chin. J. Org. Chem28, 1501–1514.
Zeng, W.-L. & Jian, F. (2009). Acta Cryst. E65, o1875.
Zeng, W.-L., Zhang, H.-X. & Jian, F.-F. (2009). Acta Cryst. E65, o2035.

Figures

[Figure ID: Fap1]
Fig. 1. 

The molecular structure of (I), drawn with 30% probability displacement ellipsoids.



Tables
[TableWrap ID: d1e118]
C16H15FO4 Z = 2
Mr = 290.28 F(000) = 304
Triclinic, P1 Dx = 1.405 Mg m3
Hall symbol: -P 1 Mo Kα radiation, λ = 0.71073 Å
a = 5.6690 (11) Å Cell parameters from 2481 reflections
b = 10.130 (2) Å θ = 3.4–27.5°
c = 12.160 (2) Å µ = 0.11 mm1
α = 100.68 (3)° T = 293 K
β = 90.73 (3)° Block, colourless
γ = 91.20 (3)° 0.25 × 0.18 × 0.12 mm
V = 686.0 (2) Å3

[TableWrap ID: d1e251]
Bruker SMART CCD area-detector diffractometer 2481 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube Rint = 0.029
graphite θmax = 27.5°, θmin = 3.4°
phi and ω scans h = −6→7
6753 measured reflections k = −13→13
3124 independent reflections l = −15→15

[TableWrap ID: d1e347]
Refinement on F2 Primary atom site location: structure-invariant direct methods
Least-squares matrix: full Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127 H-atom parameters constrained
S = 1.11 w = 1/[σ2(Fo2) + (0.075P)2 + 0.0414P] where P = (Fo2 + 2Fc2)/3
3124 reflections (Δ/σ)max < 0.001
190 parameters Δρmax = 0.22 e Å3
0 restraints Δρmin = −0.22 e Å3

[TableWrap ID: d1e504]
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.

[TableWrap ID: d1e603]
x y z Uiso*/Ueq
O4 0.41354 (13) 0.17850 (9) 0.73171 (7) 0.0412 (2)
O3 0.23315 (15) 0.01227 (9) 0.59454 (6) 0.0443 (2)
O2 0.54128 (17) 0.12738 (11) 0.89002 (8) 0.0566 (3)
O1 0.19126 (18) −0.19449 (10) 0.62363 (8) 0.0542 (3)
C8 0.21663 (19) −0.07730 (12) 0.66337 (10) 0.0397 (3)
F1 −0.52419 (17) −0.46737 (10) 0.87835 (8) 0.0718 (3)
C7 0.41388 (19) 0.09907 (13) 0.80943 (9) 0.0390 (3)
C11 −0.0075 (2) −0.18139 (12) 0.86756 (9) 0.0386 (3)
C9 0.25581 (19) −0.02211 (12) 0.78410 (9) 0.0369 (3)
C4 0.23557 (19) 0.15348 (12) 0.64363 (9) 0.0373 (3)
C15 −0.3686 (2) −0.29703 (14) 0.79341 (12) 0.0483 (3)
H15A −0.4931 −0.3097 0.7417 0.058*
C10 0.1751 (2) −0.07673 (12) 0.86916 (10) 0.0395 (3)
H10A 0.2448 −0.0435 0.9387 0.047*
C14 −0.3539 (2) −0.37296 (13) 0.87486 (11) 0.0477 (3)
C5 −0.00563 (19) 0.19627 (13) 0.68678 (10) 0.0398 (3)
H5A −0.0431 0.1530 0.7494 0.048*
H5B −0.1233 0.1671 0.6282 0.048*
C16 −0.1937 (2) −0.20081 (13) 0.78976 (11) 0.0446 (3)
H16A −0.2004 −0.1483 0.7347 0.053*
C3 0.3168 (2) 0.22760 (16) 0.55360 (11) 0.0510 (3)
H3A 0.2194 0.1992 0.4869 0.061*
H3B 0.4783 0.2043 0.5348 0.061*
C13 −0.1757 (3) −0.35709 (15) 0.95384 (11) 0.0526 (3)
H13A −0.1711 −0.4106 1.0082 0.063*
C12 −0.0029 (2) −0.25937 (14) 0.95053 (10) 0.0473 (3)
H12A 0.1176 −0.2457 1.0043 0.057*
C6 −0.0155 (2) 0.34786 (14) 0.72405 (12) 0.0522 (3)
H6A −0.1749 0.3723 0.7460 0.063*
H6B 0.0879 0.3758 0.7887 0.063*
C2 0.3031 (3) 0.37944 (17) 0.59021 (14) 0.0625 (4)
H2A 0.4182 0.4098 0.6497 0.075*
H2B 0.3421 0.4226 0.5277 0.075*
C1 0.0590 (3) 0.42054 (17) 0.63108 (15) 0.0642 (4)
H1A −0.0536 0.3997 0.5692 0.077*
H1B 0.0590 0.5168 0.6584 0.077*

[TableWrap ID: d1e1138]
U11 U22 U33 U12 U13 U23
O4 0.0287 (4) 0.0539 (5) 0.0422 (4) −0.0084 (3) −0.0059 (3) 0.0136 (4)
O3 0.0462 (5) 0.0525 (5) 0.0318 (4) 0.0047 (4) 0.0000 (3) 0.0016 (4)
O2 0.0543 (5) 0.0664 (6) 0.0495 (5) −0.0195 (5) −0.0240 (4) 0.0156 (5)
O1 0.0602 (6) 0.0480 (5) 0.0484 (5) −0.0020 (4) 0.0003 (4) −0.0067 (4)
C8 0.0311 (5) 0.0475 (7) 0.0380 (6) 0.0005 (5) 0.0000 (4) 0.0010 (5)
F1 0.0644 (6) 0.0712 (6) 0.0810 (6) −0.0309 (5) −0.0030 (5) 0.0207 (5)
C7 0.0310 (5) 0.0482 (6) 0.0372 (6) −0.0030 (5) −0.0034 (4) 0.0074 (5)
C11 0.0361 (5) 0.0410 (6) 0.0376 (6) 0.0002 (4) 0.0015 (4) 0.0046 (5)
C9 0.0314 (5) 0.0411 (6) 0.0366 (5) −0.0003 (4) −0.0036 (4) 0.0034 (5)
C4 0.0291 (5) 0.0487 (6) 0.0333 (5) −0.0018 (4) −0.0031 (4) 0.0065 (5)
C15 0.0362 (6) 0.0545 (7) 0.0530 (7) −0.0033 (5) −0.0068 (5) 0.0078 (6)
C10 0.0369 (6) 0.0432 (6) 0.0372 (6) −0.0014 (5) −0.0047 (5) 0.0052 (5)
C14 0.0420 (6) 0.0451 (7) 0.0539 (7) −0.0085 (5) 0.0047 (5) 0.0049 (6)
C5 0.0282 (5) 0.0493 (7) 0.0414 (6) −0.0010 (5) −0.0013 (4) 0.0077 (5)
C16 0.0383 (6) 0.0495 (7) 0.0481 (7) 0.0010 (5) −0.0037 (5) 0.0152 (6)
C3 0.0416 (6) 0.0738 (9) 0.0413 (6) −0.0025 (6) 0.0023 (5) 0.0203 (6)
C13 0.0590 (8) 0.0550 (8) 0.0468 (7) −0.0084 (6) −0.0006 (6) 0.0184 (6)
C12 0.0471 (7) 0.0560 (7) 0.0389 (6) −0.0066 (6) −0.0049 (5) 0.0098 (5)
C6 0.0469 (7) 0.0505 (7) 0.0573 (8) 0.0049 (6) −0.0003 (6) 0.0047 (6)
C2 0.0610 (8) 0.0695 (10) 0.0644 (9) −0.0146 (7) −0.0041 (7) 0.0339 (8)
C1 0.0693 (9) 0.0531 (8) 0.0738 (10) 0.0022 (7) −0.0094 (8) 0.0216 (7)

[TableWrap ID: d1e1561]
O4—C7 1.3500 (15) C14—C13 1.371 (2)
O4—C4 1.4458 (13) C5—C6 1.5208 (19)
O3—C8 1.3463 (16) C5—H5A 0.9700
O3—C4 1.4440 (15) C5—H5B 0.9700
O2—C7 1.1972 (14) C16—H16A 0.9300
O1—C8 1.2008 (15) C3—C2 1.524 (2)
C8—C9 1.4830 (16) C3—H3A 0.9700
F1—C14 1.3511 (15) C3—H3B 0.9700
C7—C9 1.4872 (16) C13—C12 1.3845 (19)
C11—C12 1.3922 (17) C13—H13A 0.9300
C11—C16 1.3948 (17) C12—H12A 0.9300
C11—C10 1.4635 (17) C6—C1 1.519 (2)
C9—C10 1.3411 (17) C6—H6A 0.9700
C4—C3 1.5092 (18) C6—H6B 0.9700
C4—C5 1.5138 (16) C2—C1 1.517 (2)
C15—C14 1.365 (2) C2—H2A 0.9700
C15—C16 1.3827 (18) C2—H2B 0.9700
C15—H15A 0.9300 C1—H1A 0.9700
C10—H10A 0.9300 C1—H1B 0.9700
C7—O4—C4 118.46 (9) H5A—C5—H5B 108.0
C8—O3—C4 118.15 (9) C15—C16—C11 120.91 (12)
O1—C8—O3 119.04 (11) C15—C16—H16A 119.5
O1—C8—C9 124.97 (12) C11—C16—H16A 119.5
O3—C8—C9 115.69 (10) C4—C3—C2 112.08 (12)
O2—C7—O4 119.51 (11) C4—C3—H3A 109.2
O2—C7—C9 125.10 (12) C2—C3—H3A 109.2
O4—C7—C9 115.36 (9) C4—C3—H3B 109.2
C12—C11—C16 118.66 (11) C2—C3—H3B 109.2
C12—C11—C10 118.86 (11) H3A—C3—H3B 107.9
C16—C11—C10 122.37 (11) C14—C13—C12 118.29 (13)
C10—C9—C8 125.84 (11) C14—C13—H13A 120.9
C10—C9—C7 118.84 (10) C12—C13—H13A 120.9
C8—C9—C7 115.16 (11) C13—C12—C11 120.75 (12)
O3—C4—O4 108.60 (10) C13—C12—H12A 119.6
O3—C4—C3 106.43 (10) C11—C12—H12A 119.6
O4—C4—C3 106.66 (10) C1—C6—C5 111.29 (12)
O3—C4—C5 110.87 (10) C1—C6—H6A 109.4
O4—C4—C5 111.68 (9) C5—C6—H6A 109.4
C3—C4—C5 112.35 (11) C1—C6—H6B 109.4
C14—C15—C16 118.30 (12) C5—C6—H6B 109.4
C14—C15—H15A 120.8 H6A—C6—H6B 108.0
C16—C15—H15A 120.8 C1—C2—C3 111.48 (13)
C9—C10—C11 128.90 (11) C1—C2—H2A 109.3
C9—C10—H10A 115.6 C3—C2—H2A 109.3
C11—C10—H10A 115.6 C1—C2—H2B 109.3
F1—C14—C15 118.41 (12) C3—C2—H2B 109.3
F1—C14—C13 118.51 (13) H2A—C2—H2B 108.0
C15—C14—C13 123.08 (12) C2—C1—C6 110.99 (13)
C4—C5—C6 111.58 (11) C2—C1—H1A 109.4
C4—C5—H5A 109.3 C6—C1—H1A 109.4
C6—C5—H5A 109.3 C2—C1—H1B 109.4
C4—C5—H5B 109.3 C6—C1—H1B 109.4
C6—C5—H5B 109.3 H1A—C1—H1B 108.0

[TableWrap ID: d1e2063]
D—H···A D—H H···A D···A D—H···A
C12—H12A···O2i 0.93 2.47 3.3405 (17) 156
C10—H10A···O2 0.93 2.54 2.874 (2) 101


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