PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2009 April 1; 65(Pt 4): o686.
Published online 2009 March 6. doi:  10.1107/S1600536809007533
PMCID: PMC2968819

(1S,5R)-1-(3,4-Dichloro­phen­yl)-3-oxa­bicyclo­[3.1.0]hexan-2-one

Abstract

The absolute structure has been determined by X-ray analysis for the title compound, C11H8Cl2O2. The five-membered ring of the mol­ecule is best described as a flattened envelope conformation with the methyl­ene C atom located 0.208 (2) Å below the plane formed by the other four atoms. A weak intermolecular C—H(...)O hydrogen bond is present in the crystal structure

Related literature

The title compound was prepared as an inter­mediate in the search for potential triple neurotransmittor reuptake inhibitors, see: Milewska et al. (1996 [triangle]); Lin & Charette (2005 [triangle]); Tsuji et al. (1999 [triangle]); Džolić et al. (2003 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0o686-scheme1.jpg

Experimental

Crystal data

  • C11H8Cl2O2
  • M r = 243.07
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o686-efi1.jpg
  • a = 7.0597 (4) Å
  • b = 11.1343 (7) Å
  • c = 12.6756 (8) Å
  • V = 996.36 (11) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.62 mm−1
  • T = 102 K
  • 0.58 × 0.36 × 0.18 mm

Data collection

  • Bruker APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.680, T max = 0.894
  • 8562 measured reflections
  • 2341 independent reflections
  • 2278 reflections with I > 2σ(I)
  • R int = 0.018

Refinement

  • R[F 2 > 2σ(F 2)] = 0.024
  • wR(F 2) = 0.063
  • S = 1.10
  • 2341 reflections
  • 160 parameters
  • Only H-atom coordinates refined
  • Δρmax = 0.43 e Å−3
  • Δρmin = −0.20 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 952 Friedel pairs
  • Flack parameter: 0.04 (5)

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT-Plus (Bruker, 2007 [triangle]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809007533/xu2480sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809007533/xu2480Isup2.hkl

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

supplementary crystallographic information

Comment

The title compound was prepared as an intermediate in the search for potential triple neurotransmittor reuptake inhibitors (Milewska et al., 1996; Lin & Charette, 2005; Tsuji et al., 1999; Džolić et al., 2003); details will be published elsewhere.

The molecular structure is shown in Fig. 1. The five-membered ring of the molecule is best described as a flat envelope conformation with C1 located 0.208 (2) Å below the plane constituted by C2, C4, C5 and O1, on the opposite side of C3. In the crystal structure the weak C—H···O hydrogen bonding presents between benzene ring and the carbonyl O atom of the neighboring molecule (Table 1).

Experimental

Block-shaped single crystals were obtained from an acetonitrile solution by slow evaporation at room temperature.

Refinement

Positional parameters were refined for all H atoms, Uiso(H) values were set to 1.2Ueq(C).

Figures

Fig. 1.
The molecular structure of the title compound. Displacement ellipsoids are shown at the 50% probability level and H atoms are shown as spheres of arbitrary size.

Crystal data

C11H8Cl2O2Dx = 1.620 Mg m3
Mr = 243.07Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 6286 reflections
a = 7.0597 (4) Åθ = 2.4–27.9°
b = 11.1343 (7) ŵ = 0.62 mm1
c = 12.6756 (8) ÅT = 102 K
V = 996.36 (11) Å3Block, colourless
Z = 40.58 × 0.36 × 0.18 mm
F(000) = 496

Data collection

Bruker APEXII CCD diffractometer2341 independent reflections
Radiation source: fine-focus sealed tube2278 reflections with I > 2σ(I)
graphiteRint = 0.018
Detector resolution: 8.3 pixels mm-1θmax = 27.9°, θmin = 2.4°
Sets of exposures each taken over 0.5° ω rotation scansh = −9→8
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)k = −14→14
Tmin = 0.680, Tmax = 0.894l = −16→16
8562 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.024Only H-atom coordinates refined
wR(F2) = 0.063w = 1/[σ2(Fo2) + (0.0387P)2 + 0.112P] where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max = 0.001
2341 reflectionsΔρmax = 0.43 e Å3
160 parametersΔρmin = −0.20 e Å3
0 restraintsAbsolute structure: Flack (1983), 952 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.04 (5)

Special details

Experimental. Crystallized from acetonitrile solution
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. Data were collected by measuring three sets of exposures with the detector set at 2θ = 29°, crystal-to-detector distance 6.00 cm. Refinement of F2 against ALL reflections.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Cl10.76710 (6)1.02347 (3)0.53880 (3)0.02383 (10)
Cl20.76768 (6)0.86335 (3)0.33094 (3)0.02003 (10)
O10.89020 (18)0.30003 (10)0.51020 (9)0.0219 (2)
O20.7597 (2)0.41878 (9)0.38886 (8)0.0258 (3)
C10.9599 (2)0.30985 (14)0.61831 (12)0.0195 (3)
H111.095 (3)0.3243 (17)0.6145 (14)0.023*
H120.928 (3)0.2377 (17)0.6515 (15)0.023*
C20.8628 (2)0.41790 (14)0.66439 (13)0.0162 (3)
H210.921 (2)0.4618 (19)0.7169 (15)0.019*
C30.6531 (2)0.41869 (15)0.65659 (14)0.0183 (3)
H310.586 (3)0.469 (2)0.6993 (15)0.022*
H320.590 (3)0.3471 (17)0.6365 (14)0.022*
C40.7718 (2)0.48380 (12)0.57217 (10)0.0153 (3)
C50.8034 (2)0.40360 (13)0.47933 (12)0.0191 (3)
C60.7654 (2)0.61725 (12)0.56086 (11)0.0154 (3)
C70.7598 (2)0.68907 (12)0.65134 (10)0.0174 (3)
H710.756 (3)0.6558 (15)0.7143 (14)0.021*
C80.7586 (2)0.81285 (12)0.64365 (11)0.0183 (3)
H810.746 (3)0.8709 (14)0.7047 (13)0.022*
C90.7631 (2)0.86805 (11)0.54561 (11)0.0167 (3)
C100.7664 (2)0.79786 (12)0.45517 (10)0.0155 (3)
C110.7674 (2)0.67269 (12)0.46254 (11)0.0156 (3)
H1110.776 (3)0.6262 (14)0.4035 (14)0.019*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0310 (2)0.01352 (15)0.02696 (19)0.00112 (17)−0.00448 (17)0.00012 (12)
Cl20.02456 (18)0.01897 (16)0.01656 (16)−0.00227 (16)−0.00294 (15)0.00519 (12)
O10.0341 (6)0.0156 (5)0.0160 (5)−0.0008 (5)0.0016 (5)−0.0023 (4)
O20.0423 (7)0.0211 (5)0.0141 (5)−0.0054 (6)−0.0031 (6)−0.0004 (4)
C10.0258 (8)0.0161 (7)0.0165 (7)0.0021 (6)0.0009 (6)0.0023 (6)
C20.0203 (7)0.0157 (7)0.0126 (7)0.0001 (6)−0.0008 (6)0.0010 (6)
C30.0216 (7)0.0158 (7)0.0175 (8)−0.0008 (6)0.0022 (6)0.0030 (6)
C40.0186 (7)0.0153 (6)0.0120 (6)−0.0015 (6)−0.0015 (5)0.0013 (5)
C50.0255 (8)0.0142 (6)0.0176 (7)−0.0050 (6)0.0003 (6)−0.0004 (5)
C60.0142 (6)0.0156 (6)0.0165 (6)−0.0012 (6)−0.0012 (6)0.0015 (5)
C70.0194 (7)0.0192 (6)0.0137 (6)−0.0003 (7)−0.0009 (6)0.0018 (5)
C80.0179 (7)0.0194 (6)0.0176 (6)0.0010 (7)−0.0016 (6)−0.0029 (5)
C90.0157 (6)0.0129 (6)0.0215 (7)−0.0006 (6)−0.0034 (6)0.0003 (5)
C100.0140 (7)0.0171 (6)0.0153 (6)−0.0010 (6)−0.0019 (6)0.0045 (5)
C110.0154 (7)0.0168 (6)0.0144 (6)−0.0012 (6)−0.0010 (6)0.0003 (5)

Geometric parameters (Å, °)

Cl1—C91.7329 (13)C3—H320.949 (19)
Cl2—C101.7353 (13)C4—C61.4934 (18)
O1—C51.3631 (19)C4—C51.4940 (19)
O1—C11.4602 (19)C6—C111.3909 (18)
O2—C51.1996 (18)C6—C71.3988 (19)
C1—C21.503 (2)C7—C81.3817 (19)
C1—H110.97 (2)C7—H710.880 (17)
C1—H120.93 (2)C8—C91.3868 (19)
C2—C31.484 (2)C8—H811.012 (17)
C2—C41.522 (2)C9—C101.3877 (19)
C2—H210.92 (2)C10—C111.3968 (19)
C3—C41.541 (2)C11—H1110.912 (17)
C3—H310.91 (2)
C5—O1—C1110.94 (12)C5—C4—C3110.31 (12)
O1—C1—C2105.73 (13)C2—C4—C357.96 (9)
O1—C1—H11107.3 (11)O2—C5—O1120.62 (14)
C2—C1—H11109.6 (12)O2—C5—C4129.07 (14)
O1—C1—H12106.0 (12)O1—C5—C4110.28 (13)
C2—C1—H12113.7 (11)C11—C6—C7118.77 (12)
H11—C1—H12113.8 (16)C11—C6—C4121.82 (12)
C3—C2—C1115.72 (15)C7—C6—C4119.40 (12)
C3—C2—C461.65 (11)C8—C7—C6120.84 (13)
C1—C2—C4106.25 (13)C8—C7—H71118.9 (11)
C3—C2—H21119.1 (11)C6—C7—H71120.3 (11)
C1—C2—H21120.2 (12)C7—C8—C9120.34 (12)
C4—C2—H21119.1 (13)C7—C8—H81125.7 (9)
C2—C3—C460.40 (11)C9—C8—H81113.8 (9)
C2—C3—H31118.9 (12)C8—C9—C10119.42 (12)
C4—C3—H31113.9 (13)C8—C9—Cl1119.18 (10)
C2—C3—H32118.9 (11)C10—C9—Cl1121.40 (10)
C4—C3—H32117.8 (11)C9—C10—C11120.45 (12)
H31—C3—H32115.4 (18)C9—C10—Cl2120.87 (10)
C6—C4—C5121.57 (12)C11—C10—Cl2118.68 (10)
C6—C4—C2124.48 (12)C6—C11—C10120.18 (13)
C5—C4—C2104.70 (11)C6—C11—H111118.9 (10)
C6—C4—C3121.22 (12)C10—C11—H111120.8 (10)
C1—C2—C4—C55.85 (15)C3—C4—C5—O1−57.45 (16)
O1—C1—C2—C4−12.38 (16)C2—C4—C6—C11148.81 (15)
C2—C4—C5—O13.36 (16)C3—C4—C6—C11−140.85 (15)
C5—C4—C6—C117.2 (2)C5—C4—C6—C7−171.84 (15)
C5—O1—C1—C215.19 (17)C2—C4—C6—C7−30.3 (2)
O1—C1—C2—C353.50 (19)C3—C4—C6—C740.1 (2)
C1—C2—C3—C4−95.34 (15)C11—C6—C7—C8−0.7 (3)
C3—C2—C4—C6108.17 (17)C4—C6—C7—C8178.38 (15)
C1—C2—C4—C6−140.96 (15)C6—C7—C8—C9−0.1 (3)
C3—C2—C4—C5−105.02 (14)C7—C8—C9—C100.8 (3)
C1—C2—C4—C55.85 (15)C7—C8—C9—Cl1−178.46 (14)
C1—C2—C4—C3110.87 (16)C8—C9—C10—C11−0.7 (2)
C2—C3—C4—C6−113.68 (15)Cl1—C9—C10—C11178.55 (12)
C2—C3—C4—C595.02 (14)C8—C9—C10—Cl2178.79 (13)
C1—O1—C5—O2169.94 (16)Cl1—C9—C10—Cl2−1.94 (19)
C1—O1—C5—C4−11.76 (17)C7—C6—C11—C100.8 (2)
C6—C4—C5—O2−30.5 (3)C4—C6—C11—C10−178.25 (14)
C2—C4—C5—O2−178.54 (17)C9—C10—C11—C6−0.1 (2)
C3—C4—C5—O2120.66 (19)Cl2—C10—C11—C6−179.64 (12)
C6—C4—C5—O1151.37 (14)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C7—H71···O2i0.880 (18)2.366 (18)3.2443 (16)175.6 (16)

Symmetry codes: (i) −x+3/2, −y+1, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2480).

References

  • Bruker (2007). APEX2 and SAINT-Plus Bruker AXS, Inc., Madison, Wisconsin, USA.
  • Džolić, Z., Krištafor, V., Cetina, M., Nagl, A., Hergold-Brundić, A., Mrvoš-Sermek, D., Burgemeister, T., Grdiša, M., Slade, N., Pavelic, K., Balzarini, J., De Clercq, E. & Mintas, M. (2003). Nucleosides Nucleotides Nucleic Acids, 22, 373–389. [PubMed]
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Lin, W. & Charette, A. B. (2005). Adv. Synth. Catal.347, 1547–1552.
  • Milewska, M. J., Gdaniec, M. & Poloński, T. (1996). Tetrahedron Asymmetry, 7, 3169–3180.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Tsuji, T., Onishi, T. & Sakata, K. (1999). Tetrahedron Asymmetry, 10, 3819–3825.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography