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

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COMMUNICATIONS
ISSN: 2056-9890

2-[(4-Chloro­phen­yl)(2-hy­dr­oxy-5-oxo­cyclo­pent-1-en-1-yl)meth­yl]-3-hy­dr­oxy­cyclo­pent-2-en-1-one

aSchool of Chemical Engineering and Technology, China University of Mining and Technology, Xuzhou Jiangsu 221116, People's Republic of China, and bSchool of Environment Science and Spatial Informatics, China University of Mining and Technology, Xuzhou Jiangsu 221116, People's Republic of China
*Correspondence e-mail: pjcai@cumt.edu.cn

(Received 17 April 2012; accepted 26 April 2012; online 12 May 2012)

There are two mol­ecules in the asymmetric unit of the title compound, C17H15ClO4, in which the dihedral angles between the five-membered rings are 57.3 (1) and 51.4 (1)°. An intra­molecular O—H⋯O hydrogen bond occurs in each mol­ecule. In the crystal, O—H⋯O and C—H⋯O hydrogen bonds link the moleclues into chains along the b axis.

Related literature

For the ability of carbon atoms to act as proton donors in hydrogen bonds, see: Allen et al. (1996[Allen, F. H., Lommerse, J. P. M., Hoy, V. J., Howard, J. A. K. & Desiraju, G. R. (1996). Acta Cryst. B52, 734-745.]); Sutor (1963[Sutor, D. J. (1963). J. Chem. Soc. pp. 1105-1110.]); Venkatesan et al. (2004[Venkatesan, V., Fujii, A., Ebata, T. & Mikami, N. (2004). Chem. Phys. Lett. 394, 45-48.]); Wang et al. (2005[Wang, X. S., Zeng, Z. S., Shi, D. Q., Tu, S. J., Wei, X. Y. & Zong, Z. M. (2005). J. Chem. Crystallogr. 35, 1011-1016.]); Zhu et al. (2005[Zhu, X. Q., Wang, J. S. & Cheng, J. P. (2005). Tetrahedron Lett. 46, 877-879.]).

[Scheme 1]

Experimental

Crystal data
  • C17H15ClO4

  • Mr = 318.74

  • Monoclinic, P 21 /c

  • a = 14.177 (2) Å

  • b = 10.4002 (18) Å

  • c = 21.347 (4) Å

  • β = 100.621 (2)°

  • V = 3093.6 (9) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.26 mm−1

  • T = 296 K

  • 0.36 × 0.19 × 0.13 mm

Data collection
  • Bruker SMART APEXII CCD area-detector diffractometer

  • 21681 measured reflections

  • 5521 independent reflections

  • 4756 reflections with I > 2σ(I)

  • Rint = 0.020

Refinement
  • R[F2 > 2σ(F2)] = 0.037

  • wR(F2) = 0.105

  • S = 1.03

  • 5521 reflections

  • 414 parameters

  • 4 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.35 e Å−3

  • Δρmin = −0.36 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O5—H5⋯O7 0.87 (2) 1.66 (2) 2.529 (2) 171 (3)
O3—H3⋯O1 0.87 (2) 1.70 (2) 2.558 (2) 169 (3)
O2—H2⋯O4i 0.86 (2) 1.69 (2) 2.5424 (16) 173 (3)
O8—H8⋯O6ii 0.86 (2) 1.71 (2) 2.5564 (16) 171 (2)
C9—H9A⋯O5iii 0.97 2.52 3.277 (2) 134
Symmetry codes: (i) [-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) [-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

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

Supporting information


Comment top

The ability of carbon atoms to act as proton donors in hydrogen bonds has been recognized for many years and reports of these non-classical hydrogen bonds have been reported in crystallographic studies (Allen et al., 1996; Sutor, 1963; Zhu et al., 2005; Wang et al., 2005) and spectroscopic studies (Venkatesan et al., 2004). We continue the study of such interactions with the crystal structure of the title compound.

In its crystal structure, there are two independent molecules in the asymmetric unit. All of the five-membered rings are planar. In molecule 1, the dihedral angles between the benzene ring and the two cyclopentene rings are 86.8 (1)° and 65.6 (1)°; the angle between the two five membered rings is 57.3 (1)°. In molecule 2, the dihedral angles between the benzene ring and the two cyclopentene rings are 73.1 (1)° and 80.0 (1)°; the angle between the two five membered rings is 51.4 (1)°.

The intermolecular hydrogen bonds O2—H2···O4, O8—H8···O6 and C9—H9A···O5 link adjacent moleclues, forming an infinite one-dimensional chain along the b axis. Furthermore, each molecule of the asymmetric unit exhibits an intramolecular O—H···O hydrogen bond.

Related literature top

For the ability of carbon atoms to act as proton donors in hydrogen bonds, see: Allen et al. (1996); Sutor (1963); Venkatesan et al. (2004); Wang et al. (2005); Zhu et al. (2005).

Experimental top

The title compound was prepared by the reaction of 4-chlorobenzaldehyde (0.146 g, 1.0 mmol), cyclopentane-1,3-dione (0.196 g, 2.0 mmol), and liquid 1-butyl-3-methylimidazolium bromide (2.0 ml) for 8 h at 353 K (yield 76%, mp. 517–519 K). Crystals suitable for X-ray diffraction were obtained by slow evaporation of a dimethylformamide solution.

Refinement top

The oxygen-bound H atoms were positioned geometrically and refined to distance values in the range O—H = 0.856 (15) - 0.872 (16) Å. Carbon-bound H atoms were positioned geometrically and refined as riding, with C—H = 0.93–0.98 Å, and with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 structure of the asymmetric unit, showing 30% probability displacement ellipsoids. Hydrogen atoms are shown as spheres of arbitrary radius.
[Figure 2] Fig. 2. The packing diagram of the crystal structure. Dashed lines indicate hydrogen bonds.
2-[(4-Chlorophenyl)(2-hydroxy-5-oxocyclopent-1-en-1-yl)methyl]- 3-hydroxycyclopent-2-en-1-one top
Crystal data top
C17H15ClO4Dx = 1.369 Mg m3
Mr = 318.74Melting point = 517–519 K
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 14.177 (2) ÅCell parameters from 9980 reflections
b = 10.4002 (18) Åθ = 2.4–26.8°
c = 21.347 (4) ŵ = 0.26 mm1
β = 100.621 (2)°T = 296 K
V = 3093.6 (9) Å3Block, colourless
Z = 80.36 × 0.19 × 0.13 mm
F(000) = 1328
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
4756 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.020
Graphite monochromatorθmax = 25.2°, θmin = 2.6°
phi and ω scansh = 1615
21681 measured reflectionsk = 1212
5521 independent reflectionsl = 2524
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)] = 0.037H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.105 w = 1/[σ2(Fo2) + (0.0562P)2 + 0.8138P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
5521 reflectionsΔρmax = 0.35 e Å3
414 parametersΔρmin = 0.36 e Å3
4 restraintsExtinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0128 (9)
Crystal data top
C17H15ClO4V = 3093.6 (9) Å3
Mr = 318.74Z = 8
Monoclinic, P21/cMo Kα radiation
a = 14.177 (2) ŵ = 0.26 mm1
b = 10.4002 (18) ÅT = 296 K
c = 21.347 (4) Å0.36 × 0.19 × 0.13 mm
β = 100.621 (2)°
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
4756 reflections with I > 2σ(I)
21681 measured reflectionsRint = 0.020
5521 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0374 restraints
wR(F2) = 0.105H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.35 e Å3
5521 reflectionsΔρmin = 0.36 e Å3
414 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
Cl10.41647 (4)0.38936 (6)0.09436 (3)0.07932 (19)
Cl20.63726 (5)0.49872 (9)0.63868 (3)0.1039 (3)
O10.83676 (10)0.43037 (13)0.01202 (6)0.0663 (4)
O20.98385 (10)0.45352 (13)0.22616 (6)0.0683 (4)
H21.0287 (16)0.411 (2)0.2498 (11)0.104 (9)*
O30.81942 (10)0.67287 (14)0.00658 (6)0.0623 (3)
H30.8184 (19)0.5912 (17)0.0018 (13)0.101 (9)*
O40.89094 (9)0.81138 (12)0.20647 (6)0.0597 (3)
O50.88325 (9)0.38226 (15)0.40367 (8)0.0732 (4)
H50.8578 (17)0.4582 (18)0.3958 (12)0.088 (8)*
O60.62092 (10)0.14135 (13)0.30146 (8)0.0812 (5)
O70.81303 (9)0.60024 (13)0.36945 (6)0.0637 (3)
O80.50411 (8)0.49232 (11)0.26293 (5)0.0459 (3)
H80.4609 (14)0.5355 (19)0.2384 (9)0.073 (6)*
C10.88850 (12)0.40357 (16)0.06380 (8)0.0512 (4)
C20.95946 (15)0.29362 (19)0.07285 (11)0.0694 (5)
H2A1.00540.30290.04460.083*
H2B0.92660.21200.06410.083*
C31.00944 (14)0.30107 (18)0.14210 (11)0.0686 (5)
H3A1.00010.22260.16480.082*
H3B1.07770.31640.14550.082*
C40.96129 (11)0.41267 (15)0.16725 (8)0.0492 (4)
C50.89209 (10)0.46855 (14)0.12298 (7)0.0411 (3)
C60.82777 (10)0.57674 (13)0.13687 (7)0.0379 (3)
H6A0.84480.59030.18300.045*
C70.84653 (9)0.70428 (13)0.10769 (7)0.0379 (3)
C80.87748 (10)0.81257 (14)0.14737 (8)0.0429 (3)
C90.89172 (12)0.92755 (15)0.10751 (9)0.0524 (4)
H9A0.95710.95900.11830.063*
H9B0.84820.99640.11360.063*
C100.87011 (12)0.87857 (17)0.03931 (9)0.0533 (4)
H10A0.81780.92640.01410.064*
H10B0.92620.88520.01940.064*
C110.84274 (10)0.74123 (15)0.04599 (7)0.0446 (4)
C120.72287 (10)0.53369 (13)0.12508 (6)0.0382 (3)
C130.65039 (11)0.59634 (16)0.08441 (8)0.0490 (4)
H13A0.66510.66870.06250.059*
C140.55591 (12)0.55379 (19)0.07543 (8)0.0572 (4)
H14A0.50790.59750.04800.069*
C150.53436 (12)0.44653 (17)0.10748 (8)0.0523 (4)
C160.60432 (13)0.38306 (17)0.14920 (9)0.0565 (4)
H16A0.58900.31130.17130.068*
C170.69758 (12)0.42716 (15)0.15791 (8)0.0498 (4)
H17A0.74480.38470.18650.060*
C180.82774 (11)0.29123 (17)0.37395 (8)0.0518 (4)
C190.87382 (14)0.1676 (2)0.36041 (11)0.0701 (5)
H19A0.90610.12730.39950.084*
H19B0.91990.18130.33270.084*
C200.79055 (16)0.0862 (2)0.32786 (12)0.0773 (6)
H20A0.79910.06140.28550.093*
H20B0.78430.00910.35240.093*
C210.70359 (12)0.17179 (16)0.32464 (8)0.0531 (4)
C220.73116 (10)0.29280 (14)0.35387 (7)0.0410 (3)
C230.65710 (10)0.39155 (13)0.36304 (7)0.0372 (3)
H23A0.59500.35150.34640.045*
C240.65913 (10)0.51265 (14)0.32455 (7)0.0386 (3)
C250.58503 (11)0.55632 (14)0.27997 (7)0.0391 (3)
C260.60407 (13)0.68375 (15)0.25230 (8)0.0510 (4)
H26A0.55790.74770.26030.061*
H26B0.60200.67730.20670.061*
C270.70464 (13)0.71664 (16)0.28730 (9)0.0566 (4)
H27A0.74820.72580.25750.068*
H27B0.70430.79630.31090.068*
C280.73447 (12)0.60596 (15)0.33194 (7)0.0470 (4)
C290.65562 (10)0.42008 (14)0.43328 (7)0.0386 (3)
C300.68823 (13)0.33059 (18)0.48066 (8)0.0548 (4)
H30A0.71420.25340.46990.066*
C310.68270 (14)0.3545 (2)0.54350 (9)0.0666 (5)
H31A0.70510.29400.57480.080*
C320.64416 (13)0.4677 (2)0.55949 (8)0.0626 (5)
C330.60995 (13)0.55753 (19)0.51394 (9)0.0581 (4)
H33A0.58290.63370.52510.070*
C340.61633 (11)0.53321 (16)0.45121 (8)0.0465 (4)
H34A0.59370.59430.42030.056*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0615 (3)0.0993 (4)0.0808 (3)0.0363 (3)0.0224 (2)0.0124 (3)
Cl20.1052 (5)0.1636 (7)0.0512 (3)0.0229 (4)0.0355 (3)0.0156 (3)
O10.0814 (9)0.0606 (8)0.0530 (7)0.0008 (7)0.0025 (6)0.0173 (6)
O20.0733 (9)0.0634 (8)0.0587 (8)0.0239 (7)0.0124 (6)0.0061 (6)
O30.0812 (9)0.0623 (8)0.0424 (6)0.0042 (7)0.0092 (6)0.0008 (6)
O40.0650 (8)0.0558 (7)0.0537 (7)0.0155 (6)0.0012 (6)0.0125 (5)
O50.0374 (6)0.0698 (9)0.1046 (11)0.0064 (6)0.0072 (6)0.0178 (8)
O60.0644 (9)0.0553 (8)0.1104 (12)0.0106 (6)0.0193 (8)0.0238 (7)
O70.0544 (7)0.0615 (8)0.0717 (8)0.0214 (6)0.0024 (6)0.0070 (6)
O80.0395 (6)0.0471 (6)0.0490 (6)0.0049 (5)0.0023 (5)0.0088 (5)
C10.0516 (9)0.0432 (9)0.0596 (10)0.0035 (7)0.0129 (8)0.0102 (7)
C20.0729 (12)0.0506 (10)0.0890 (14)0.0098 (9)0.0259 (11)0.0139 (10)
C30.0571 (11)0.0494 (10)0.0983 (15)0.0155 (8)0.0121 (10)0.0000 (10)
C40.0442 (9)0.0394 (8)0.0625 (10)0.0038 (6)0.0058 (7)0.0046 (7)
C50.0385 (8)0.0353 (7)0.0483 (8)0.0001 (6)0.0050 (6)0.0013 (6)
C60.0411 (8)0.0365 (7)0.0338 (7)0.0031 (6)0.0010 (6)0.0018 (5)
C70.0298 (7)0.0378 (7)0.0445 (8)0.0019 (5)0.0022 (6)0.0001 (6)
C80.0295 (7)0.0422 (8)0.0546 (9)0.0010 (6)0.0012 (6)0.0043 (6)
C90.0392 (8)0.0396 (8)0.0776 (12)0.0026 (6)0.0082 (8)0.0013 (8)
C100.0436 (9)0.0508 (9)0.0670 (11)0.0027 (7)0.0143 (8)0.0144 (8)
C110.0375 (8)0.0477 (9)0.0474 (8)0.0021 (6)0.0049 (6)0.0032 (7)
C120.0447 (8)0.0357 (7)0.0346 (7)0.0003 (6)0.0089 (6)0.0042 (6)
C130.0450 (9)0.0511 (9)0.0483 (9)0.0078 (7)0.0012 (7)0.0091 (7)
C140.0456 (9)0.0706 (12)0.0522 (9)0.0086 (8)0.0005 (7)0.0054 (8)
C150.0518 (9)0.0597 (10)0.0489 (9)0.0163 (8)0.0180 (7)0.0124 (8)
C160.0653 (11)0.0472 (9)0.0647 (11)0.0057 (8)0.0318 (9)0.0018 (8)
C170.0555 (10)0.0447 (9)0.0526 (9)0.0072 (7)0.0186 (7)0.0076 (7)
C180.0378 (8)0.0546 (10)0.0612 (10)0.0008 (7)0.0041 (7)0.0077 (8)
C190.0521 (10)0.0676 (12)0.0901 (14)0.0150 (9)0.0121 (10)0.0083 (10)
C200.0744 (13)0.0565 (11)0.0993 (16)0.0124 (10)0.0111 (11)0.0210 (11)
C210.0536 (10)0.0442 (9)0.0572 (10)0.0023 (7)0.0009 (8)0.0079 (7)
C220.0374 (7)0.0404 (8)0.0432 (8)0.0013 (6)0.0025 (6)0.0035 (6)
C230.0304 (7)0.0366 (7)0.0421 (7)0.0042 (5)0.0004 (5)0.0006 (6)
C240.0404 (8)0.0386 (7)0.0377 (7)0.0026 (6)0.0094 (6)0.0027 (6)
C250.0454 (8)0.0373 (7)0.0372 (7)0.0040 (6)0.0146 (6)0.0011 (6)
C260.0673 (11)0.0408 (8)0.0491 (9)0.0051 (7)0.0216 (8)0.0056 (7)
C270.0710 (11)0.0411 (9)0.0644 (10)0.0083 (8)0.0297 (9)0.0014 (8)
C280.0512 (9)0.0441 (8)0.0484 (8)0.0093 (7)0.0166 (7)0.0084 (7)
C290.0304 (7)0.0425 (8)0.0424 (7)0.0059 (6)0.0056 (6)0.0023 (6)
C300.0576 (10)0.0560 (10)0.0520 (9)0.0051 (8)0.0129 (8)0.0113 (8)
C310.0658 (12)0.0877 (15)0.0475 (10)0.0002 (10)0.0133 (8)0.0200 (9)
C320.0511 (10)0.0955 (15)0.0449 (9)0.0167 (10)0.0183 (8)0.0052 (9)
C330.0524 (10)0.0649 (11)0.0614 (11)0.0092 (8)0.0219 (8)0.0140 (9)
C340.0428 (8)0.0469 (9)0.0506 (9)0.0018 (6)0.0110 (7)0.0002 (7)
Geometric parameters (Å, º) top
Cl1—C151.7471 (17)C13—H13A0.9300
Cl2—C321.7414 (18)C14—C151.372 (3)
O1—C11.240 (2)C14—H14A0.9300
O2—C41.310 (2)C15—C161.374 (3)
O2—H20.858 (17)C16—C171.379 (2)
O3—C111.318 (2)C16—H16A0.9300
O3—H30.869 (17)C17—H17A0.9300
O4—C81.2407 (19)C18—C221.357 (2)
O5—C181.317 (2)C18—C191.495 (3)
O5—H50.872 (16)C19—C201.513 (3)
O6—C211.227 (2)C19—H19A0.9700
O7—C281.247 (2)C19—H19B0.9700
O8—C251.3182 (18)C20—C211.512 (3)
O8—H80.856 (15)C20—H20A0.9700
C1—C51.425 (2)C20—H20B0.9700
C1—C21.512 (3)C21—C221.427 (2)
C2—C31.519 (3)C22—C231.507 (2)
C2—H2A0.9700C23—C241.507 (2)
C2—H2B0.9700C23—C291.532 (2)
C3—C41.495 (2)C23—H23A0.9800
C3—H3A0.9700C24—C251.359 (2)
C3—H3B0.9700C24—C281.430 (2)
C4—C51.361 (2)C25—C261.496 (2)
C5—C61.512 (2)C26—C271.522 (3)
C6—C71.510 (2)C26—H26A0.9700
C6—C121.529 (2)C26—H26B0.9700
C6—H6A0.9800C27—C281.504 (2)
C7—C111.364 (2)C27—H27A0.9700
C7—C81.429 (2)C27—H27B0.9700
C8—C91.503 (2)C29—C341.386 (2)
C9—C101.520 (3)C29—C301.389 (2)
C9—H9A0.9700C30—C311.381 (3)
C9—H9B0.9700C30—H30A0.9300
C10—C111.494 (2)C31—C321.367 (3)
C10—H10A0.9700C31—H31A0.9300
C10—H10B0.9700C32—C331.371 (3)
C12—C131.380 (2)C33—C341.382 (2)
C12—C171.393 (2)C33—H33A0.9300
C13—C141.390 (2)C34—H34A0.9300
C4—O2—H2114.9 (18)C16—C17—H17A119.1
C11—O3—H3111.2 (18)C12—C17—H17A119.1
C18—O5—H5111.7 (17)O5—C18—C22128.46 (16)
C25—O8—H8113.0 (15)O5—C18—C19117.91 (15)
O1—C1—C5127.01 (15)C22—C18—C19113.62 (15)
O1—C1—C2123.65 (16)C18—C19—C20103.78 (15)
C5—C1—C2109.34 (15)C18—C19—H19A111.0
C1—C2—C3105.41 (15)C20—C19—H19A111.0
C1—C2—H2A110.7C18—C19—H19B111.0
C3—C2—H2A110.7C20—C19—H19B111.0
C1—C2—H2B110.7H19A—C19—H19B109.0
C3—C2—H2B110.7C21—C20—C19104.60 (15)
H2A—C2—H2B108.8C21—C20—H20A110.8
C4—C3—C2103.13 (15)C19—C20—H20A110.8
C4—C3—H3A111.1C21—C20—H20B110.8
C2—C3—H3A111.1C19—C20—H20B110.8
C4—C3—H3B111.1H20A—C20—H20B108.9
C2—C3—H3B111.1O6—C21—C22124.64 (16)
H3A—C3—H3B109.1O6—C21—C20125.22 (16)
O2—C4—C5123.05 (15)C22—C21—C20110.13 (14)
O2—C4—C3123.33 (15)C18—C22—C21107.86 (14)
C5—C4—C3113.62 (16)C18—C22—C23130.81 (14)
C4—C5—C1108.45 (14)C21—C22—C23121.10 (13)
C4—C5—C6124.43 (14)C24—C23—C22114.51 (12)
C1—C5—C6127.05 (13)C24—C23—C29112.14 (12)
C7—C6—C5114.49 (12)C22—C23—C29113.24 (11)
C7—C6—C12115.42 (11)C24—C23—H23A105.3
C5—C6—C12110.69 (11)C22—C23—H23A105.3
C7—C6—H6A105.0C29—C23—H23A105.3
C5—C6—H6A105.0C25—C24—C28108.40 (14)
C12—C6—H6A105.0C25—C24—C23124.83 (13)
C11—C7—C8107.68 (13)C28—C24—C23126.57 (13)
C11—C7—C6131.89 (13)O8—C25—C24123.07 (13)
C8—C7—C6120.40 (13)O8—C25—C26123.34 (13)
O4—C8—C7124.60 (14)C24—C25—C26113.59 (14)
O4—C8—C9124.90 (14)C25—C26—C27103.07 (13)
C7—C8—C9110.50 (13)C25—C26—H26A111.1
C8—C9—C10104.56 (13)C27—C26—H26A111.1
C8—C9—H9A110.8C25—C26—H26B111.1
C10—C9—H9A110.8C27—C26—H26B111.1
C8—C9—H9B110.8H26A—C26—H26B109.1
C10—C9—H9B110.8C28—C27—C26105.52 (13)
H9A—C9—H9B108.9C28—C27—H27A110.6
C11—C10—C9103.83 (13)C26—C27—H27A110.6
C11—C10—H10A111.0C28—C27—H27B110.6
C9—C10—H10A111.0C26—C27—H27B110.6
C11—C10—H10B111.0H27A—C27—H27B108.8
C9—C10—H10B111.0O7—C28—C24126.78 (15)
H10A—C10—H10B109.0O7—C28—C27123.81 (15)
O3—C11—C7129.01 (15)C24—C28—C27109.40 (14)
O3—C11—C10117.60 (14)C34—C29—C30117.67 (15)
C7—C11—C10113.39 (14)C34—C29—C23120.89 (13)
C13—C12—C17117.47 (14)C30—C29—C23121.32 (14)
C13—C12—C6123.65 (13)C31—C30—C29121.05 (17)
C17—C12—C6118.87 (13)C31—C30—H30A119.5
C12—C13—C14121.54 (15)C29—C30—H30A119.5
C12—C13—H13A119.2C32—C31—C30119.64 (17)
C14—C13—H13A119.2C32—C31—H31A120.2
C15—C14—C13119.18 (16)C30—C31—H31A120.2
C15—C14—H14A120.4C31—C32—C33121.00 (17)
C13—C14—H14A120.4C31—C32—Cl2119.89 (16)
C14—C15—C16120.89 (16)C33—C32—Cl2119.11 (17)
C14—C15—Cl1119.41 (14)C32—C33—C34119.00 (18)
C16—C15—Cl1119.70 (14)C32—C33—H33A120.5
C15—C16—C17119.17 (16)C34—C33—H33A120.5
C15—C16—H16A120.4C33—C34—C29121.64 (16)
C17—C16—H16A120.4C33—C34—H34A119.2
C16—C17—C12121.72 (16)C29—C34—H34A119.2
O1—C1—C2—C3177.35 (18)O5—C18—C19—C20178.89 (19)
C5—C1—C2—C32.3 (2)C22—C18—C19—C200.2 (2)
C1—C2—C3—C41.3 (2)C18—C19—C20—C210.9 (2)
C2—C3—C4—O2179.42 (17)C19—C20—C21—O6179.9 (2)
C2—C3—C4—C50.2 (2)C19—C20—C21—C221.3 (2)
O2—C4—C5—C1177.93 (16)O5—C18—C22—C21179.57 (19)
C3—C4—C5—C11.6 (2)C19—C18—C22—C210.5 (2)
O2—C4—C5—C64.9 (3)O5—C18—C22—C235.2 (3)
C3—C4—C5—C6175.49 (15)C19—C18—C22—C23173.81 (17)
O1—C1—C5—C4177.19 (17)O6—C21—C22—C18179.83 (19)
C2—C1—C5—C42.5 (2)C20—C21—C22—C181.1 (2)
O1—C1—C5—C65.8 (3)O6—C21—C22—C234.8 (3)
C2—C1—C5—C6174.57 (15)C20—C21—C22—C23173.88 (16)
C4—C5—C6—C7110.93 (17)C18—C22—C23—C2472.4 (2)
C1—C5—C6—C772.47 (19)C21—C22—C23—C24113.89 (16)
C4—C5—C6—C12116.52 (16)C18—C22—C23—C2957.9 (2)
C1—C5—C6—C1260.1 (2)C21—C22—C23—C29115.82 (15)
C5—C6—C7—C1160.0 (2)C22—C23—C24—C25119.43 (15)
C12—C6—C7—C1170.2 (2)C29—C23—C24—C25109.75 (15)
C5—C6—C7—C8117.54 (14)C22—C23—C24—C2866.24 (18)
C12—C6—C7—C8112.20 (14)C29—C23—C24—C2864.58 (18)
C11—C7—C8—O4178.14 (14)C28—C24—C25—O8179.23 (13)
C6—C7—C8—O40.1 (2)C23—C24—C25—O84.0 (2)
C11—C7—C8—C91.64 (17)C28—C24—C25—C260.67 (17)
C6—C7—C8—C9179.73 (12)C23—C24—C25—C26175.88 (13)
O4—C8—C9—C10177.76 (14)O8—C25—C26—C27179.57 (14)
C7—C8—C9—C102.02 (17)C24—C25—C26—C270.33 (17)
C8—C9—C10—C111.57 (16)C25—C26—C27—C280.13 (16)
C8—C7—C11—O3178.88 (15)C25—C24—C28—O7178.60 (16)
C6—C7—C11—O31.1 (3)C23—C24—C28—O73.5 (3)
C8—C7—C11—C100.56 (17)C25—C24—C28—C270.74 (17)
C6—C7—C11—C10178.35 (14)C23—C24—C28—C27175.84 (14)
C9—C10—C11—O3179.79 (14)C26—C27—C28—O7178.84 (15)
C9—C10—C11—C70.69 (18)C26—C27—C28—C240.52 (17)
C7—C6—C12—C137.8 (2)C24—C23—C29—C3427.75 (18)
C5—C6—C12—C13124.24 (16)C22—C23—C29—C34159.21 (13)
C7—C6—C12—C17170.70 (13)C24—C23—C29—C30156.14 (14)
C5—C6—C12—C1757.23 (17)C22—C23—C29—C3024.67 (19)
C17—C12—C13—C141.2 (2)C34—C29—C30—C310.8 (2)
C6—C12—C13—C14179.74 (15)C23—C29—C30—C31177.04 (15)
C12—C13—C14—C150.4 (3)C29—C30—C31—C320.3 (3)
C13—C14—C15—C161.6 (3)C30—C31—C32—C330.7 (3)
C13—C14—C15—Cl1177.84 (14)C30—C31—C32—Cl2179.82 (14)
C14—C15—C16—C171.1 (3)C31—C32—C33—C341.1 (3)
Cl1—C15—C16—C17178.33 (13)Cl2—C32—C33—C34179.40 (13)
C15—C16—C17—C120.6 (3)C32—C33—C34—C290.5 (2)
C13—C12—C17—C161.7 (2)C30—C29—C34—C330.4 (2)
C6—C12—C17—C16179.68 (14)C23—C29—C34—C33176.63 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5···O70.87 (2)1.66 (2)2.529 (2)171 (3)
O3—H3···O10.87 (2)1.70 (2)2.558 (2)169 (3)
O2—H2···O4i0.86 (2)1.69 (2)2.5424 (16)173 (3)
O8—H8···O6ii0.86 (2)1.71 (2)2.5564 (16)171 (2)
C9—H9A···O5iii0.972.523.277 (2)134
Symmetry codes: (i) x+2, y1/2, z+1/2; (ii) x+1, y+1/2, z+1/2; (iii) x+2, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC17H15ClO4
Mr318.74
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)14.177 (2), 10.4002 (18), 21.347 (4)
β (°) 100.621 (2)
V3)3093.6 (9)
Z8
Radiation typeMo Kα
µ (mm1)0.26
Crystal size (mm)0.36 × 0.19 × 0.13
Data collection
DiffractometerBruker SMART APEXII CCD area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
21681, 5521, 4756
Rint0.020
(sin θ/λ)max1)0.599
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.105, 1.03
No. of reflections5521
No. of parameters414
No. of restraints4
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.35, 0.36

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5···O70.872 (16)1.664 (17)2.529 (2)171 (3)
O3—H3···O10.869 (17)1.701 (18)2.558 (2)169 (3)
O2—H2···O4i0.858 (17)1.688 (18)2.5424 (16)173 (3)
O8—H8···O6ii0.856 (15)1.708 (16)2.5564 (16)171 (2)
C9—H9A···O5iii0.972.523.277 (2)134.4
Symmetry codes: (i) x+2, y1/2, z+1/2; (ii) x+1, y+1/2, z+1/2; (iii) x+2, y+1/2, z+1/2.
 

Acknowledgements

We are grateful to the National Natural Science Foundation of China (Nos. 51174201, 50921002), the Fundamental Research Funds for the Central Universities (No. 2010QNB09), the PhD Programs Foundation of the Ministry of Education of China (No. 20090095120011),and the Open Foundation of Southwest University of Science and Technology (No. 11zxjk10) for financial support.

References

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First citationSutor, D. J. (1963). J. Chem. Soc. pp. 1105–1110.  CrossRef Web of Science Google Scholar
First citationVenkatesan, V., Fujii, A., Ebata, T. & Mikami, N. (2004). Chem. Phys. Lett. 394, 45–48.  Web of Science CrossRef CAS Google Scholar
First citationWang, X. S., Zeng, Z. S., Shi, D. Q., Tu, S. J., Wei, X. Y. & Zong, Z. M. (2005). J. Chem. Crystallogr. 35, 1011–1016.  Google Scholar
First citationZhu, X. Q., Wang, J. S. & Cheng, J. P. (2005). Tetrahedron Lett. 46, 877–879.  Web of Science CrossRef CAS Google Scholar

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