organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

Methyl (Z)-2-chloro-3-(2-meth­oxy­carbonyl­phen­yl)prop-2-enoate

aDepartment of Chemistry and Biochemistry, Arizona State University, Tempe, Arizona 85287-1604, USA
*Correspondence e-mail: tgroy@asu.edu

(Received 25 November 2009; accepted 7 January 2010; online 16 January 2010)

In the title compound, C12H11ClO4, the propenoate C=C bond is in the Z configuration. The propenoate C=O and C=C groups are essentially coplanar [C=C—C=O torsion angle = 172.4 (3)°] with the O atom synperiplanar to the Cl atom. However, the π systems of the aromatic ring and chloro­propenoate substituent are not coplanar; the corresponding dihedral angle is 51.5 (1)°. The noncoplanarity is likely due to steric inter­actions between the propenoate H atom and the ortho-methoxy­carbonyl group on the aromatic ring. Even in the observed noncoplanar conformation, the ortho C=O to H distance (2.40 Å) is less than the sum of the van der Waals radii of O and H (2.65 Å).

Related literature

For the structure of 2-nitro­cinnamic acid, in which the alkene group is noncoplanar with the aromatic ring, as in the title compound, see: Smith et al. (2006[Smith, G., Wermuth, U. D., Young, D. J. & White, J. M. (2006). Acta Cryst. E62, o2024-o2026.]). For numerous structures of cinnamic acid derivatives, with coplanar aromatic and alkene groups, see: ethyl p-methoxy­cinnamate (Luger et al., 1996[Luger, P., Weber, M., Dung, N. X. & Tuyet, N. T. B. (1996). Acta Cryst. C52, 1255-1257.]), p-cresyl cinnamate (Kaitner & Stilinović, 2007[Kaitner, B. & Stilinović, V. (2007). Acta Cryst. E63, o4347.]), 4-methyl­coumarin ester of trans-cinnamic acid (Yang et al., 2006[Yang, S.-P., Han, L.-J., Xia, H.-T. & Wang, D.-Q. (2006). Acta Cryst. E62, o4181-o4182.]), methyl esters of m- and p-bromo­cinnamic acids (Leiserowitz & Schmidt, 1965[Leiserowitz, L. & Schmidt, G. M. J. (1965). Acta Cryst. 18, 1058-1067.]), methyl 3,5-dinitro-trans-cinnamate (Sharma et al., 1995[Sharma, C. V. K., Panneerselvam, K., Desiraju, G. R. & Pilati, T. (1995). Acta Cryst. C51, 1364-1366.]), N-cinnamoylsaccharin (Ersanlı et al., 2005[Ersanlı, C. C., Odabaşoğlu, M., Sarı, U. & Erdönmez, A. (2005). Acta Cryst. C61, o243-o245.]), and 2-ethoxy­cinnamic acid (Fernandes et al., 2001[Fernandes, M. A., Levendis, D. C. & de Koning, C. B. (2001). Cryst. Eng. 4, 215-231.]). For the chlorination step of the synthesis, see: Markó et al. (1997[Markó, I. E., Richardson, P. R., Bailey, M., Maguire, A. R. & Coughlan, N. (1997). Tetrahedron Lett. 38, 2339-2342.]). For van der Waals radii, see: Rowland & Taylor (1996[Rowland, R. S. & Taylor, R. (1996). J. Phys. Chem. 100, 7384-7391.]).

[Scheme 1]

Experimental

Crystal data
  • C12H11ClO4

  • Mr = 254.66

  • Monoclinic, P 21 /c

  • a = 10.722 (5) Å

  • b = 15.331 (7) Å

  • c = 7.676 (4) Å

  • β = 110.395 (10)°

  • V = 1182.7 (10) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.32 mm−1

  • T = 299 K

  • 0.40 × 0.10 × 0.04 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, BIS, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.882, Tmax = 0.988

  • 9313 measured reflections

  • 2110 independent reflections

  • 1559 reflections with I > 2σ(I)

  • Rint = 0.036

Refinement
  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 0.096

  • S = 1.01

  • 2110 reflections

  • 156 parameters

  • H-atom parameters constrained

  • Δρmax = 0.21 e Å−3

  • Δρmin = −0.18 e Å−3

Data collection: APEX2 and BIS (Bruker, 2008[Bruker (2008). APEX2, BIS, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, BIS, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: XSHELL (Bruker, 2004[Bruker (2004). XSHELL. Bruker AXS Inc., Madison, Wisconsin, USA.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

The title compound (1) is of interest in the development of anticancer enzyme inhibitors. Determination of the E/Z stereochemistry and the preferred conformation were needed for in silico docking of 1 and its derivatives to target enzymes.

Synthesis of 1 was carried out as shown in Fig. 1. Esterification of o-carboxycinnamic acid was accomplished by treatment with CH3OH/HCl. The subsequent formation of the Z-isomer during synthesis can be rationalized on the basis of the known lack of stereospecificity of the dichlorination reaction when applied to aromatic-substituted alkenes, carried out essentially by the method of Markó et al. (1997).

Subsequent elimination of HCl from the dichloro derivative by treatment with triethylamine in dichloromethane produced 1 in ~10:1 ratio (by NMR) with its E isomer. Regioselectivity (i.e., preferential formation of the 2-chloropropenoate over 3-chloropropenoate) results from the more facile deprotonation of the more acidic H atom in the α-position to the ester carbonyl group, with loss of the 3-chlorine atom.

Fig. 2 shows that 1 has Z configuration at the alkene double bond and that the π systems of the aromatic ring and the chloropropenoate substituent are not coplanar. The C2—C1—C7—C8 torsion angle is 133.5 (3)° and the C6—C1—C7—C8 torsion angle is -49.4 (4)°; the dihedral angle formed by the plane of the aromatic ring and the plane of the chloropropenoate substituent (C7, C8, C9, Cl1, O1, O2) is equal to 51.5 (1)°. The ortho-methoxycarbonyl substituent is slightly non-coplanar with the aromatic ring, as shown by the O3—C11—C2—C1 torsion angle of -10.7 (4)°. Loss of resonance stabilization by twisting of the ortho-methoxycarbonyl and propenoate groups relative to the aromatic ring is presumably balanced by relief of steric strain due to proximity of the ortho-carbonyl oxygen and the propenoate hydrogen.

Related literature top

For the structure of 2-nitrocinnamic acid, in which the alkene group is noncoplanar with the aromatic ring, as in the title compound, see: Smith et al. (2006). For numerous structures of cinnamic acid derivatives, with coplanar aromatic and alkene groups, see: ethyl p-methoxycinnamate (Luger et al., 1996), p-cresyl cinnamate (Kaitner & Stilinović, 2007), 4-methylcoumarin ester of trans-cinnamic acid (Yang et al., 2006), methyl esters of m- and p-bromocinnamic acids (Leiserowitz & Schmidt, 1965), methyl 3,5-dinitro-trans-cinnamate (Sharma et al., 1995), N-cinnamoylsaccharin (Ersanlı et al., 2005), and 2-ethoxycinnamic acid (Fernandes et al., 2001). For the chlorination step of the synthesis, see: Markó et al. (1997). For van der Waals radii, see: Rowland & Taylor (1996).

Experimental top

2-Carboxycinnamic acid (2-CCA) dimethyl ester.

Acetyl chloride (1 ml) was slowly added to 25 ml of cold methanol in a 100-ml round-bottom flask. The reaction mixture was warmed slowly then refluxed for 10 minutes prior to addition of 381 mg (2 mmol) of 2-CCA. The reaction mixture was refluxed and monitored by thin-layer chromatography (TLC). Typically, the reaction was complete in less than 2 h. The reaction mixture was concentrated by rotary evaporation and passed through a short silica gel column with dichloromethane elution to yield 420 mg (~95%) of a viscous, clear oil.

Dichlorination of 2-CCA dimethyl ester.

KMnO4 (730 mg, 4.62 mmol) and benzyltriethylammonium chloride (1.040 g, 4.57 mmol) were stirred in 20 ml of dry dichloromethane. The resulting dark purple solution was cooled on ice for 20 min. Chlorotrimethylsilane (~2 g, 18.4 mmol) was slowly added to the stirred solution, which gradually took on a dark green color. The reaction mixture was allowed to warm to room temperature, and 2-CCA dimethyl ester (1 g, 4.55 mmol) was added. The reaction mixture was monitored by TLC, but the reaction was terminated prior to completion because of reagent degradation (green color vanishing and dark or brown color appearing, along with multiple spots appearing upon TLC). The organic solution was successively washed with 0.1 M sodium thiosulfate and brine, followed by drying over anhydrous sodium sulfate. A silica gel column was used to separate the mixture (elution with 1:1 hexanes–chloroform). Recrystallization from dichloromethane/hexanes yielded 640 mg of white solid. M.p. 70.5–72 °C. 1H NMR (400 MHz in CDCl3) δ, 7.97 (d, 1H, J = 8.0 Hz), 7.69 (d, 1H, J = 7.6 Hz), 7.60 (t, 1H, J = 7.6 Hz), 7.44 (app t, 1H, J = 7.6, 8.0 Hz), 6.62 (d, 1H, J = 10.4 Hz), 4.75 (d, 1H, 10.4 Hz), 3.95 (s, 3H), 3.88 (s, 3H); 13C NMR (100 MHz in CDCl3) δ, 167.5, 167.0, 137.7, 132.6, 130.6, 130.0, 128.9, 128.6, 59.2, 55.8, 53.4, 52.6. Anal. Calcd (%) for C12H11ClO4: C, 49.51; H, 4.15. Found: C, 49.30; H, 4.11.

Elimination of HCl to form 1.

In 2 ml of dichloromethane was dissolved 300 mg (1.03 mmol) of the above dichloro ester. Triethylamine (110 mg, 1.10 mmol) was then added, and the reaction was monitored by TLC. The reaction mixture was washed successively with ~5 ml of 1.0 M HCl and brine, followed by drying over anhydrous sodium sulfate. Formation of an approximately 10:1 ratio of 1 to its E isomer was indicated by 1H NMR spectroscopy of the crude product. Subsequent crystallizations from dichloromethane/hexanes yielded ~90 mg of white solid, 1 (0.35 mmol, 34%). 1H NMR (500 MHz in CDCl3) δ, 8.45 (s, 1H), 8.05 (d, 1H, J = 12.5 Hz), 7.66 (d, 1H, J = 8 Hz), 7.57 (app t, 1H, J = 12.5, 8 Hz), 7.44 (app t, 1H, J = 8, 7.5 Hz), 3.90 (s, 3H), 3.88 (s, 3H).

Refinement top

All H-atoms were placed geometrically (C—H 0.93 and 0.96 Å for aromatic and methyl H atoms respectively) and included in the refinement in the riding motion approximation with Uiso(H) = 1.2Ueq(C) for CH and Uiso(H) = 1.5Ueq(C) for CH3.

Structure description top

The title compound (1) is of interest in the development of anticancer enzyme inhibitors. Determination of the E/Z stereochemistry and the preferred conformation were needed for in silico docking of 1 and its derivatives to target enzymes.

Synthesis of 1 was carried out as shown in Fig. 1. Esterification of o-carboxycinnamic acid was accomplished by treatment with CH3OH/HCl. The subsequent formation of the Z-isomer during synthesis can be rationalized on the basis of the known lack of stereospecificity of the dichlorination reaction when applied to aromatic-substituted alkenes, carried out essentially by the method of Markó et al. (1997).

Subsequent elimination of HCl from the dichloro derivative by treatment with triethylamine in dichloromethane produced 1 in ~10:1 ratio (by NMR) with its E isomer. Regioselectivity (i.e., preferential formation of the 2-chloropropenoate over 3-chloropropenoate) results from the more facile deprotonation of the more acidic H atom in the α-position to the ester carbonyl group, with loss of the 3-chlorine atom.

Fig. 2 shows that 1 has Z configuration at the alkene double bond and that the π systems of the aromatic ring and the chloropropenoate substituent are not coplanar. The C2—C1—C7—C8 torsion angle is 133.5 (3)° and the C6—C1—C7—C8 torsion angle is -49.4 (4)°; the dihedral angle formed by the plane of the aromatic ring and the plane of the chloropropenoate substituent (C7, C8, C9, Cl1, O1, O2) is equal to 51.5 (1)°. The ortho-methoxycarbonyl substituent is slightly non-coplanar with the aromatic ring, as shown by the O3—C11—C2—C1 torsion angle of -10.7 (4)°. Loss of resonance stabilization by twisting of the ortho-methoxycarbonyl and propenoate groups relative to the aromatic ring is presumably balanced by relief of steric strain due to proximity of the ortho-carbonyl oxygen and the propenoate hydrogen.

For the structure of 2-nitrocinnamic acid, in which the alkene group is noncoplanar with the aromatic ring, as in the title compound, see: Smith et al. (2006). For numerous structures of cinnamic acid derivatives, with coplanar aromatic and alkene groups, see: ethyl p-methoxycinnamate (Luger et al., 1996), p-cresyl cinnamate (Kaitner & Stilinović, 2007), 4-methylcoumarin ester of trans-cinnamic acid (Yang et al., 2006), methyl esters of m- and p-bromocinnamic acids (Leiserowitz & Schmidt, 1965), methyl 3,5-dinitro-trans-cinnamate (Sharma et al., 1995), N-cinnamoylsaccharin (Ersanlı et al., 2005), and 2-ethoxycinnamic acid (Fernandes et al., 2001). For the chlorination step of the synthesis, see: Markó et al. (1997). For van der Waals radii, see: Rowland & Taylor (1996).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XSHELL (Bruker, 2004); software used to prepare material for publication: APEX2 (Bruker, 2008).

Figures top
[Figure 1] Fig. 1. Outline of the synthesis of 1. See Markó et al. (1997) for details.
[Figure 2] Fig. 2. Molecular structure of 1 illustrating the lack of coplanarity of the aromatic ring and chloropropenoate substituent. Thermal displacement ellipsoids are drawn at the 50% probability level.
Methyl (Z)-2-chloro-3-(2-methoxycarbonylphenyl)prop-2-enoate top
Crystal data top
C12H11ClO4F(000) = 528
Mr = 254.66Dx = 1.430 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 536 reflections
a = 10.722 (5) Åθ = 2.4–21.4°
b = 15.331 (7) ŵ = 0.32 mm1
c = 7.676 (4) ÅT = 299 K
β = 110.395 (10)°Needle, colourless
V = 1182.7 (10) Å30.40 × 0.10 × 0.04 mm
Z = 4
Data collection top
Bruker SMART APEX CCD
diffractometer
2110 independent reflections
Radiation source: sealed tube1559 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
Detector resolution: 8.3330 pixels mm-1θmax = 25.2°, θmin = 2.0°
ω and φ scansh = 1212
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
k = 1818
Tmin = 0.882, Tmax = 0.988l = 89
9313 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0409P)2 + 0.4245P]
where P = (Fo2 + 2Fc2)/3
2110 reflections(Δ/σ)max < 0.001
156 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.18 e Å3
Crystal data top
C12H11ClO4V = 1182.7 (10) Å3
Mr = 254.66Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.722 (5) ŵ = 0.32 mm1
b = 15.331 (7) ÅT = 299 K
c = 7.676 (4) Å0.40 × 0.10 × 0.04 mm
β = 110.395 (10)°
Data collection top
Bruker SMART APEX CCD
diffractometer
2110 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
1559 reflections with I > 2σ(I)
Tmin = 0.882, Tmax = 0.988Rint = 0.036
9313 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.096H-atom parameters constrained
S = 1.01Δρmax = 0.21 e Å3
2110 reflectionsΔρmin = 0.18 e Å3
156 parameters
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
Cl10.00350 (6)0.17184 (4)0.01458 (9)0.0599 (2)
O10.01434 (17)0.36083 (12)0.0476 (2)0.0699 (5)
O20.18915 (14)0.37829 (10)0.2585 (2)0.0550 (4)
O30.46537 (17)0.23575 (11)0.1480 (2)0.0734 (5)
O40.61609 (16)0.13201 (11)0.2032 (2)0.0697 (5)
C10.2933 (2)0.11550 (13)0.2545 (2)0.0420 (5)
C20.4135 (2)0.09334 (12)0.2308 (2)0.0418 (5)
C30.4545 (2)0.00641 (13)0.2476 (2)0.0493 (5)
H30.53360.00810.23040.059*
C40.3807 (2)0.05806 (14)0.2890 (2)0.0567 (5)
H40.40920.11570.29840.068*
C50.2641 (2)0.03686 (16)0.3165 (2)0.0569 (5)
H50.21430.08010.3470.068*
C60.2214 (2)0.04850 (16)0.2986 (2)0.0516 (5)
H60.14210.06190.31660.062*
C70.2465 (2)0.20628 (13)0.2425 (2)0.0442 (5)
H70.30940.24730.30750.053*
C80.1264 (2)0.23667 (13)0.1511 (2)0.0435 (5)
C90.0900 (2)0.33090 (16)0.1439 (2)0.0474 (5)
C100.1623 (2)0.46999 (14)0.2694 (4)0.0634 (7)
H10A0.13660.49540.14760.095*
H10B0.24090.49850.35010.095*
H10C0.09150.47710.31770.095*
C110.4975 (2)0.16172 (14)0.1891 (2)0.0445 (5)
C120.7057 (2)0.19250 (18)0.1647 (5)0.0712 (8)
H12A0.66210.21960.04630.107*
H12B0.78320.16190.16240.107*
H12C0.73170.23640.25980.107*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0400 (2)0.0651 (4)0.0684 (4)0.0037 (2)0.0109 (2)0.0123 (2)
O10.0565 (11)0.0651 (11)0.0728 (13)0.0194 (9)0.0032 (9)0.0021 (9)
O20.0482 (9)0.0406 (9)0.0716 (11)0.0052 (7)0.0150 (8)0.0016 (8)
O30.0528 (10)0.0453 (10)0.1248 (17)0.0069 (8)0.0344 (11)0.0199 (11)
O40.0495 (10)0.0495 (10)0.1210 (16)0.0077 (8)0.0437 (10)0.0151 (10)
C10.0402 (11)0.0401 (11)0.0417 (11)0.0016 (9)0.0092 (10)0.0038 (10)
C20.0391 (11)0.0373 (11)0.0446 (13)0.0002 (9)0.0091 (10)0.0013 (10)
C30.0444 (13)0.0423 (13)0.0576 (14)0.0029 (10)0.0131 (11)0.0022 (11)
C40.0616 (16)0.0360 (11)0.0651 (16)0.0001 (11)0.0127 (13)0.0004 (11)
C50.0609 (16)0.0467 (14)0.0594 (16)0.0116 (11)0.0164 (13)0.0031 (11)
C60.0464 (14)0.0527 (15)0.0553 (15)0.0034 (11)0.0171 (11)0.0007 (11)
C70.0388 (11)0.0438 (11)0.0485 (13)0.0016 (10)0.0133 (10)0.0033 (10)
C80.0389 (11)0.0459 (13)0.0473 (13)0.0001 (10)0.0169 (10)0.0049 (10)
C90.0429 (13)0.0556 (14)0.0467 (13)0.0066 (11)0.0196 (11)0.0030 (11)
C100.0690 (17)0.0411 (13)0.079 (2)0.0054 (11)0.0241 (15)0.0009 (13)
C110.0379 (11)0.0425 (14)0.0500 (13)0.0022 (10)0.0112 (10)0.0008 (10)
C120.0517 (16)0.0614 (17)0.112 (2)0.0011 (13)0.0425 (16)0.0077 (16)
Geometric parameters (Å, º) top
Cl1—C81.734 (2)C4—C51.378 (3)
O1—C91.197 (3)C4—H40.93
O2—C91.334 (3)C5—C61.377 (3)
O2—C101.443 (3)C5—H50.93
O3—C111.196 (3)C6—H60.93
O4—C111.319 (3)C7—C81.318 (3)
O4—C121.439 (3)C7—H70.93
C1—C61.396 (3)C8—C91.492 (3)
C1—C21.405 (3)C10—H10A0.96
C1—C71.472 (3)C10—H10B0.96
C2—C31.395 (3)C10—H10C0.96
C2—C111.487 (3)C12—H12A0.96
C3—C41.371 (3)C12—H12B0.96
C3—H30.93C12—H12C0.96
C9—O2—C10116.07 (18)C1—C7—H7116.0
C11—O4—C12117.0 (2)C7—C8—C9123.8 (2)
C6—C1—C2117.6 (2)C7—C8—Cl1123.29 (18)
C6—C1—C7120.4 (2)C9—C8—Cl1112.84 (16)
C2—C1—C7122.0 (2)O1—C9—O2123.9 (2)
C3—C2—C1119.5 (2)O1—C9—C8124.7 (2)
C3—C2—C11119.9 (2)O2—C9—C8111.4 (2)
C1—C2—C11120.6 (2)O2—C10—H10A109.5
C4—C3—C2121.5 (2)O2—C10—H10B109.5
C4—C3—H3119.3H10A—C10—H10B109.5
C2—C3—H3119.3O2—C10—H10C109.5
C3—C4—C5119.6 (2)H10A—C10—H10C109.5
C3—C4—H4120.2H10B—C10—H10C109.5
C5—C4—H4120.2O3—C11—O4122.0 (2)
C6—C5—C4119.8 (2)O3—C11—C2125.8 (2)
C6—C5—H5120.1O4—C11—C2112.2 (2)
C4—C5—H5120.1O4—C12—H12A109.5
C5—C6—C1122.1 (2)O4—C12—H12B109.5
C5—C6—H6119.0H12A—C12—H12B109.5
C1—C6—H6119.0O4—C12—H12C109.5
C8—C7—C1128.1 (2)H12A—C12—H12C109.5
C8—C7—H7116.0H12B—C12—H12C109.5
C2—C1—C7—C8133.5 (3)O3—C11—C2—C110.7 (4)
C6—C1—C7—C849.4 (3)

Experimental details

Crystal data
Chemical formulaC12H11ClO4
Mr254.66
Crystal system, space groupMonoclinic, P21/c
Temperature (K)299
a, b, c (Å)10.722 (5), 15.331 (7), 7.676 (4)
β (°) 110.395 (10)
V3)1182.7 (10)
Z4
Radiation typeMo Kα
µ (mm1)0.32
Crystal size (mm)0.40 × 0.10 × 0.04
Data collection
DiffractometerBruker SMART APEX CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2008)
Tmin, Tmax0.882, 0.988
No. of measured, independent and
observed [I > 2σ(I)] reflections
9313, 2110, 1559
Rint0.036
(sin θ/λ)max1)0.599
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.096, 1.01
No. of reflections2110
No. of parameters156
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.21, 0.18

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XSHELL (Bruker, 2004).

 

Acknowledgements

The authors thank the Arizona Biomedical Research Commission for financial support.

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