supplementary materials


Acta Cryst. (2009). E65, o686    [ doi:10.1107/S1600536809007533 ]

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

C. H. Görbitz, T. Hansen and K. Vestli

Abstract top

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

Comment top

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).

Related literature top

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

Experimental top

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

Refinement top

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

Computing details top

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

Figures top
[Figure 1] 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.
(1S,5R)-1-(3,4-dichlorophenyl)-3-oxabicyclo[3.1.0]hexan-2-one top
Crystal data top
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 top
Bruker APEXII CCD
diffractometer
2341 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 = 98
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1414
Tmin = 0.680, Tmax = 0.894l = 1616
8562 measured reflections
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)] = 0.024Only H-atom coordinates refined
wR(F2) = 0.063 w = 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)
Crystal data top
C11H8Cl2O2V = 996.36 (11) Å3
Mr = 243.07Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 7.0597 (4) ŵ = 0.62 mm1
b = 11.1343 (7) ÅT = 102 K
c = 12.6756 (8) Å0.58 × 0.36 × 0.18 mm
Data collection top
Bruker APEXII CCD
diffractometer
2341 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2278 reflections with I > 2σ(I)
Tmin = 0.680, Tmax = 0.894Rint = 0.018
8562 measured reflectionsθmax = 27.9°
Refinement top
R[F2 > 2σ(F2)] = 0.024Only H-atom coordinates refined
wR(F2) = 0.063Δρmax = 0.43 e Å3
S = 1.10Δρmin = 0.20 e Å3
2341 reflectionsAbsolute structure: Flack (1983), 952 Friedel pairs
160 parametersFlack parameter: 0.04 (5)
0 restraints
Special details top

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) top
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) top
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, °) top
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—O157.45 (16)
O1—C1—C2—C412.38 (16)C2—C4—C6—C11148.81 (15)
C2—C4—C5—O13.36 (16)C3—C4—C6—C11140.85 (15)
C5—C4—C6—C117.2 (2)C5—C4—C6—C7171.84 (15)
C5—O1—C1—C215.19 (17)C2—C4—C6—C730.3 (2)
O1—C1—C2—C353.50 (19)C3—C4—C6—C740.1 (2)
C1—C2—C3—C495.34 (15)C11—C6—C7—C80.7 (3)
C3—C2—C4—C6108.17 (17)C4—C6—C7—C8178.38 (15)
C1—C2—C4—C6140.96 (15)C6—C7—C8—C90.1 (3)
C3—C2—C4—C5105.02 (14)C7—C8—C9—C100.8 (3)
C1—C2—C4—C55.85 (15)C7—C8—C9—Cl1178.46 (14)
C1—C2—C4—C3110.87 (16)C8—C9—C10—C110.7 (2)
C2—C3—C4—C6113.68 (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—Cl21.94 (19)
C1—O1—C5—C411.76 (17)C7—C6—C11—C100.8 (2)
C6—C4—C5—O230.5 (3)C4—C6—C11—C10178.25 (14)
C2—C4—C5—O2178.54 (17)C9—C10—C11—C60.1 (2)
C3—C4—C5—O2120.66 (19)Cl2—C10—C11—C6179.64 (12)
C6—C4—C5—O1151.37 (14)
Hydrogen-bond geometry (Å, °) top
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.
Table 1
Hydrogen-bond geometry (Å, °)
top
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.
references
References top

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.

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.

Tsuji, T., Onishi, T. & Sakata, K. (1999). Tetrahedron Asymmetry, 10, 3819–3825.