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

Li, G.; Cai, P.; Huo, J.; Shi, C.

doi:10.1107/S1600536812018715

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1667

doi:10.1107/S1600536812018715

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

Gongzhen Li,^a,^b Peijun Cai,^a ^* Junhao Huo ^a and Chong Shi ^a

^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 ); Sutor (1963 ); Venkatesan et al. (2004 ); Wang et al. (2005 ); Zhu et al. (2005 ).

Experimental

Crystal data

C₁₇H₁₅ClO₄
M_r = 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)
R_int = 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
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812018715/wn2471sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812018715/wn2471Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812018715/wn2471Isup3.cml

checkCIF report

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.

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

	Fig. 1. The structure of the asymmetric unit, showing 30% probability displacement ellipsoids. Hydrogen atoms are shown as spheres of arbitrary radius.
	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

C₁₇H₁₅ClO₄	D_x = 1.369 Mg m⁻³
M_r = 318.74	Melting point = 517–519 K
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.177 (2) Å	Cell parameters from 9980 reflections
b = 10.4002 (18) Å	θ = 2.4–26.8°
c = 21.347 (4) Å	µ = 0.26 mm⁻¹
β = 100.621 (2)°	T = 296 K
V = 3093.6 (9) Å³	Block, colourless
Z = 8	0.36 × 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 tube	R_int = 0.020
Graphite monochromator	θ_max = 25.2°, θ_min = 2.6°
phi and ω scans	h = −16→15
21681 measured reflections	k = −12→12
5521 independent reflections	l = −25→24

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.105	w = 1/[σ²(F_o²) + (0.0562P)² + 0.8138P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
5521 reflections	Δρ_max = 0.35 e Å⁻³
414 parameters	Δρ_min = −0.36 e Å⁻³
4 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0128 (9)

Crystal data top

C₁₇H₁₅ClO₄	V = 3093.6 (9) Å³
M_r = 318.74	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.177 (2) Å	µ = 0.26 mm⁻¹
b = 10.4002 (18) Å	T = 296 K
c = 21.347 (4) Å	0.36 × 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 reflections	R_int = 0.020
5521 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	4 restraints
wR(F²) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.35 e Å⁻³
5521 reflections	Δρ_min = −0.36 e Å⁻³
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

	x	y	z	U_iso*/U_eq
Cl1	0.41647 (4)	0.38936 (6)	0.09436 (3)	0.07932 (19)
Cl2	0.63726 (5)	0.49872 (9)	0.63868 (3)	0.1039 (3)
O1	0.83676 (10)	0.43037 (13)	0.01202 (6)	0.0663 (4)
O2	0.98385 (10)	0.45352 (13)	0.22616 (6)	0.0683 (4)
H2	1.0287 (16)	0.411 (2)	0.2498 (11)	0.104 (9)*
O3	0.81942 (10)	0.67287 (14)	−0.00658 (6)	0.0623 (3)
H3	0.8184 (19)	0.5912 (17)	0.0018 (13)	0.101 (9)*
O4	0.89094 (9)	0.81138 (12)	0.20647 (6)	0.0597 (3)
O5	0.88325 (9)	0.38226 (15)	0.40367 (8)	0.0732 (4)
H5	0.8578 (17)	0.4582 (18)	0.3958 (12)	0.088 (8)*
O6	0.62092 (10)	0.14135 (13)	0.30146 (8)	0.0812 (5)
O7	0.81303 (9)	0.60024 (13)	0.36945 (6)	0.0637 (3)
O8	0.50411 (8)	0.49232 (11)	0.26293 (5)	0.0459 (3)
H8	0.4609 (14)	0.5355 (19)	0.2384 (9)	0.073 (6)*
C1	0.88850 (12)	0.40357 (16)	0.06380 (8)	0.0512 (4)
C2	0.95946 (15)	0.29362 (19)	0.07285 (11)	0.0694 (5)
H2A	1.0054	0.3029	0.0446	0.083*
H2B	0.9266	0.2120	0.0641	0.083*
C3	1.00944 (14)	0.30107 (18)	0.14210 (11)	0.0686 (5)
H3A	1.0001	0.2226	0.1648	0.082*
H3B	1.0777	0.3164	0.1455	0.082*
C4	0.96129 (11)	0.41267 (15)	0.16725 (8)	0.0492 (4)
C5	0.89209 (10)	0.46855 (14)	0.12298 (7)	0.0411 (3)
C6	0.82777 (10)	0.57674 (13)	0.13687 (7)	0.0379 (3)
H6A	0.8448	0.5903	0.1830	0.045*
C7	0.84653 (9)	0.70428 (13)	0.10769 (7)	0.0379 (3)
C8	0.87748 (10)	0.81257 (14)	0.14737 (8)	0.0429 (3)
C9	0.89172 (12)	0.92755 (15)	0.10751 (9)	0.0524 (4)
H9A	0.9571	0.9590	0.1183	0.063*
H9B	0.8482	0.9964	0.1136	0.063*
C10	0.87011 (12)	0.87857 (17)	0.03931 (9)	0.0533 (4)
H10A	0.8178	0.9264	0.0141	0.064*
H10B	0.9262	0.8852	0.0194	0.064*
C11	0.84274 (10)	0.74123 (15)	0.04599 (7)	0.0446 (4)
C12	0.72287 (10)	0.53369 (13)	0.12508 (6)	0.0382 (3)
C13	0.65039 (11)	0.59634 (16)	0.08441 (8)	0.0490 (4)
H13A	0.6651	0.6687	0.0625	0.059*
C14	0.55591 (12)	0.55379 (19)	0.07543 (8)	0.0572 (4)
H14A	0.5079	0.5975	0.0480	0.069*
C15	0.53436 (12)	0.44653 (17)	0.10748 (8)	0.0523 (4)
C16	0.60432 (13)	0.38306 (17)	0.14920 (9)	0.0565 (4)
H16A	0.5890	0.3113	0.1713	0.068*
C17	0.69758 (12)	0.42716 (15)	0.15791 (8)	0.0498 (4)
H17A	0.7448	0.3847	0.1865	0.060*
C18	0.82774 (11)	0.29123 (17)	0.37395 (8)	0.0518 (4)
C19	0.87382 (14)	0.1676 (2)	0.36041 (11)	0.0701 (5)
H19A	0.9061	0.1273	0.3995	0.084*
H19B	0.9199	0.1813	0.3327	0.084*
C20	0.79055 (16)	0.0862 (2)	0.32786 (12)	0.0773 (6)
H20A	0.7991	0.0614	0.2855	0.093*
H20B	0.7843	0.0091	0.3524	0.093*
C21	0.70359 (12)	0.17179 (16)	0.32464 (8)	0.0531 (4)
C22	0.73116 (10)	0.29280 (14)	0.35387 (7)	0.0410 (3)
C23	0.65710 (10)	0.39155 (13)	0.36304 (7)	0.0372 (3)
H23A	0.5950	0.3515	0.3464	0.045*
C24	0.65913 (10)	0.51265 (14)	0.32455 (7)	0.0386 (3)
C25	0.58503 (11)	0.55632 (14)	0.27997 (7)	0.0391 (3)
C26	0.60407 (13)	0.68375 (15)	0.25230 (8)	0.0510 (4)
H26A	0.5579	0.7477	0.2603	0.061*
H26B	0.6020	0.6773	0.2067	0.061*
C27	0.70464 (13)	0.71664 (16)	0.28730 (9)	0.0566 (4)
H27A	0.7482	0.7258	0.2575	0.068*
H27B	0.7043	0.7963	0.3109	0.068*
C28	0.73447 (12)	0.60596 (15)	0.33194 (7)	0.0470 (4)
C29	0.65562 (10)	0.42008 (14)	0.43328 (7)	0.0386 (3)
C30	0.68823 (13)	0.33059 (18)	0.48066 (8)	0.0548 (4)
H30A	0.7142	0.2534	0.4699	0.066*
C31	0.68270 (14)	0.3545 (2)	0.54350 (9)	0.0666 (5)
H31A	0.7051	0.2940	0.5748	0.080*
C32	0.64416 (13)	0.4677 (2)	0.55949 (8)	0.0626 (5)
C33	0.60995 (13)	0.55753 (19)	0.51394 (9)	0.0581 (4)
H33A	0.5829	0.6337	0.5251	0.070*
C34	0.61633 (11)	0.53321 (16)	0.45121 (8)	0.0465 (4)
H34A	0.5937	0.5943	0.4203	0.056*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0615 (3)	0.0993 (4)	0.0808 (3)	−0.0363 (3)	0.0224 (2)	−0.0124 (3)
Cl2	0.1052 (5)	0.1636 (7)	0.0512 (3)	−0.0229 (4)	0.0355 (3)	−0.0156 (3)
O1	0.0814 (9)	0.0606 (8)	0.0530 (7)	0.0008 (7)	0.0025 (6)	−0.0173 (6)
O2	0.0733 (9)	0.0634 (8)	0.0587 (8)	0.0239 (7)	−0.0124 (6)	0.0061 (6)
O3	0.0812 (9)	0.0623 (8)	0.0424 (6)	−0.0042 (7)	0.0092 (6)	0.0008 (6)
O4	0.0650 (8)	0.0558 (7)	0.0537 (7)	−0.0155 (6)	−0.0012 (6)	−0.0125 (5)
O5	0.0374 (6)	0.0698 (9)	0.1046 (11)	−0.0064 (6)	−0.0072 (6)	−0.0178 (8)
O6	0.0644 (9)	0.0553 (8)	0.1104 (12)	−0.0106 (6)	−0.0193 (8)	−0.0238 (7)
O7	0.0544 (7)	0.0615 (8)	0.0717 (8)	−0.0214 (6)	0.0024 (6)	−0.0070 (6)
O8	0.0395 (6)	0.0471 (6)	0.0490 (6)	0.0049 (5)	0.0023 (5)	0.0088 (5)
C1	0.0516 (9)	0.0432 (9)	0.0596 (10)	−0.0035 (7)	0.0129 (8)	−0.0102 (7)
C2	0.0729 (12)	0.0506 (10)	0.0890 (14)	0.0098 (9)	0.0259 (11)	−0.0139 (10)
C3	0.0571 (11)	0.0494 (10)	0.0983 (15)	0.0155 (8)	0.0121 (10)	0.0000 (10)
C4	0.0442 (9)	0.0394 (8)	0.0625 (10)	0.0038 (6)	0.0058 (7)	0.0046 (7)
C5	0.0385 (8)	0.0353 (7)	0.0483 (8)	0.0001 (6)	0.0050 (6)	−0.0013 (6)
C6	0.0411 (8)	0.0365 (7)	0.0338 (7)	0.0031 (6)	0.0010 (6)	−0.0018 (5)
C7	0.0298 (7)	0.0378 (7)	0.0445 (8)	0.0019 (5)	0.0022 (6)	−0.0001 (6)
C8	0.0295 (7)	0.0422 (8)	0.0546 (9)	−0.0010 (6)	0.0012 (6)	−0.0043 (6)
C9	0.0392 (8)	0.0396 (8)	0.0776 (12)	−0.0026 (6)	0.0082 (8)	0.0013 (8)
C10	0.0436 (9)	0.0508 (9)	0.0670 (11)	0.0027 (7)	0.0143 (8)	0.0144 (8)
C11	0.0375 (8)	0.0477 (9)	0.0474 (8)	0.0021 (6)	0.0049 (6)	0.0032 (7)
C12	0.0447 (8)	0.0357 (7)	0.0346 (7)	0.0003 (6)	0.0089 (6)	−0.0042 (6)
C13	0.0450 (9)	0.0511 (9)	0.0483 (9)	−0.0078 (7)	0.0012 (7)	0.0091 (7)
C14	0.0456 (9)	0.0706 (12)	0.0522 (9)	−0.0086 (8)	0.0005 (7)	0.0054 (8)
C15	0.0518 (9)	0.0597 (10)	0.0489 (9)	−0.0163 (8)	0.0180 (7)	−0.0124 (8)
C16	0.0653 (11)	0.0472 (9)	0.0647 (11)	−0.0057 (8)	0.0318 (9)	0.0018 (8)
C17	0.0555 (10)	0.0447 (9)	0.0526 (9)	0.0072 (7)	0.0186 (7)	0.0076 (7)
C18	0.0378 (8)	0.0546 (10)	0.0612 (10)	−0.0008 (7)	0.0041 (7)	−0.0077 (8)
C19	0.0521 (10)	0.0676 (12)	0.0901 (14)	0.0150 (9)	0.0121 (10)	−0.0083 (10)
C20	0.0744 (13)	0.0565 (11)	0.0993 (16)	0.0124 (10)	0.0111 (11)	−0.0210 (11)
C21	0.0536 (10)	0.0442 (9)	0.0572 (10)	−0.0023 (7)	−0.0009 (8)	−0.0079 (7)
C22	0.0374 (7)	0.0404 (8)	0.0432 (8)	−0.0013 (6)	0.0025 (6)	−0.0035 (6)
C23	0.0304 (7)	0.0366 (7)	0.0421 (7)	−0.0042 (5)	0.0004 (5)	−0.0006 (6)
C24	0.0404 (8)	0.0386 (7)	0.0377 (7)	−0.0026 (6)	0.0094 (6)	−0.0027 (6)
C25	0.0454 (8)	0.0373 (7)	0.0372 (7)	0.0040 (6)	0.0146 (6)	−0.0011 (6)
C26	0.0673 (11)	0.0408 (8)	0.0491 (9)	0.0051 (7)	0.0216 (8)	0.0056 (7)
C27	0.0710 (11)	0.0411 (9)	0.0644 (10)	−0.0083 (8)	0.0297 (9)	−0.0014 (8)
C28	0.0512 (9)	0.0441 (8)	0.0484 (8)	−0.0093 (7)	0.0166 (7)	−0.0084 (7)
C29	0.0304 (7)	0.0425 (8)	0.0424 (7)	−0.0059 (6)	0.0056 (6)	0.0023 (6)
C30	0.0576 (10)	0.0560 (10)	0.0520 (9)	0.0051 (8)	0.0129 (8)	0.0113 (8)
C31	0.0658 (12)	0.0877 (15)	0.0475 (10)	−0.0002 (10)	0.0133 (8)	0.0200 (9)
C32	0.0511 (10)	0.0955 (15)	0.0449 (9)	−0.0167 (10)	0.0183 (8)	−0.0052 (9)
C33	0.0524 (10)	0.0649 (11)	0.0614 (11)	−0.0092 (8)	0.0219 (8)	−0.0140 (9)
C34	0.0428 (8)	0.0469 (9)	0.0506 (9)	−0.0018 (6)	0.0110 (7)	−0.0002 (7)

Geometric parameters (Å, º) top

Cl1—C15	1.7471 (17)	C13—H13A	0.9300
Cl2—C32	1.7414 (18)	C14—C15	1.372 (3)
O1—C1	1.240 (2)	C14—H14A	0.9300
O2—C4	1.310 (2)	C15—C16	1.374 (3)
O2—H2	0.858 (17)	C16—C17	1.379 (2)
O3—C11	1.318 (2)	C16—H16A	0.9300
O3—H3	0.869 (17)	C17—H17A	0.9300
O4—C8	1.2407 (19)	C18—C22	1.357 (2)
O5—C18	1.317 (2)	C18—C19	1.495 (3)
O5—H5	0.872 (16)	C19—C20	1.513 (3)
O6—C21	1.227 (2)	C19—H19A	0.9700
O7—C28	1.247 (2)	C19—H19B	0.9700
O8—C25	1.3182 (18)	C20—C21	1.512 (3)
O8—H8	0.856 (15)	C20—H20A	0.9700
C1—C5	1.425 (2)	C20—H20B	0.9700
C1—C2	1.512 (3)	C21—C22	1.427 (2)
C2—C3	1.519 (3)	C22—C23	1.507 (2)
C2—H2A	0.9700	C23—C24	1.507 (2)
C2—H2B	0.9700	C23—C29	1.532 (2)
C3—C4	1.495 (2)	C23—H23A	0.9800
C3—H3A	0.9700	C24—C25	1.359 (2)
C3—H3B	0.9700	C24—C28	1.430 (2)
C4—C5	1.361 (2)	C25—C26	1.496 (2)
C5—C6	1.512 (2)	C26—C27	1.522 (3)
C6—C7	1.510 (2)	C26—H26A	0.9700
C6—C12	1.529 (2)	C26—H26B	0.9700
C6—H6A	0.9800	C27—C28	1.504 (2)
C7—C11	1.364 (2)	C27—H27A	0.9700
C7—C8	1.429 (2)	C27—H27B	0.9700
C8—C9	1.503 (2)	C29—C34	1.386 (2)
C9—C10	1.520 (3)	C29—C30	1.389 (2)
C9—H9A	0.9700	C30—C31	1.381 (3)
C9—H9B	0.9700	C30—H30A	0.9300
C10—C11	1.494 (2)	C31—C32	1.367 (3)
C10—H10A	0.9700	C31—H31A	0.9300
C10—H10B	0.9700	C32—C33	1.371 (3)
C12—C13	1.380 (2)	C33—C34	1.382 (2)
C12—C17	1.393 (2)	C33—H33A	0.9300
C13—C14	1.390 (2)	C34—H34A	0.9300

C4—O2—H2	114.9 (18)	C16—C17—H17A	119.1
C11—O3—H3	111.2 (18)	C12—C17—H17A	119.1
C18—O5—H5	111.7 (17)	O5—C18—C22	128.46 (16)
C25—O8—H8	113.0 (15)	O5—C18—C19	117.91 (15)
O1—C1—C5	127.01 (15)	C22—C18—C19	113.62 (15)
O1—C1—C2	123.65 (16)	C18—C19—C20	103.78 (15)
C5—C1—C2	109.34 (15)	C18—C19—H19A	111.0
C1—C2—C3	105.41 (15)	C20—C19—H19A	111.0
C1—C2—H2A	110.7	C18—C19—H19B	111.0
C3—C2—H2A	110.7	C20—C19—H19B	111.0
C1—C2—H2B	110.7	H19A—C19—H19B	109.0
C3—C2—H2B	110.7	C21—C20—C19	104.60 (15)
H2A—C2—H2B	108.8	C21—C20—H20A	110.8
C4—C3—C2	103.13 (15)	C19—C20—H20A	110.8
C4—C3—H3A	111.1	C21—C20—H20B	110.8
C2—C3—H3A	111.1	C19—C20—H20B	110.8
C4—C3—H3B	111.1	H20A—C20—H20B	108.9
C2—C3—H3B	111.1	O6—C21—C22	124.64 (16)
H3A—C3—H3B	109.1	O6—C21—C20	125.22 (16)
O2—C4—C5	123.05 (15)	C22—C21—C20	110.13 (14)
O2—C4—C3	123.33 (15)	C18—C22—C21	107.86 (14)
C5—C4—C3	113.62 (16)	C18—C22—C23	130.81 (14)
C4—C5—C1	108.45 (14)	C21—C22—C23	121.10 (13)
C4—C5—C6	124.43 (14)	C24—C23—C22	114.51 (12)
C1—C5—C6	127.05 (13)	C24—C23—C29	112.14 (12)
C7—C6—C5	114.49 (12)	C22—C23—C29	113.24 (11)
C7—C6—C12	115.42 (11)	C24—C23—H23A	105.3
C5—C6—C12	110.69 (11)	C22—C23—H23A	105.3
C7—C6—H6A	105.0	C29—C23—H23A	105.3
C5—C6—H6A	105.0	C25—C24—C28	108.40 (14)
C12—C6—H6A	105.0	C25—C24—C23	124.83 (13)
C11—C7—C8	107.68 (13)	C28—C24—C23	126.57 (13)
C11—C7—C6	131.89 (13)	O8—C25—C24	123.07 (13)
C8—C7—C6	120.40 (13)	O8—C25—C26	123.34 (13)
O4—C8—C7	124.60 (14)	C24—C25—C26	113.59 (14)
O4—C8—C9	124.90 (14)	C25—C26—C27	103.07 (13)
C7—C8—C9	110.50 (13)	C25—C26—H26A	111.1
C8—C9—C10	104.56 (13)	C27—C26—H26A	111.1
C8—C9—H9A	110.8	C25—C26—H26B	111.1
C10—C9—H9A	110.8	C27—C26—H26B	111.1
C8—C9—H9B	110.8	H26A—C26—H26B	109.1
C10—C9—H9B	110.8	C28—C27—C26	105.52 (13)
H9A—C9—H9B	108.9	C28—C27—H27A	110.6
C11—C10—C9	103.83 (13)	C26—C27—H27A	110.6
C11—C10—H10A	111.0	C28—C27—H27B	110.6
C9—C10—H10A	111.0	C26—C27—H27B	110.6
C11—C10—H10B	111.0	H27A—C27—H27B	108.8
C9—C10—H10B	111.0	O7—C28—C24	126.78 (15)
H10A—C10—H10B	109.0	O7—C28—C27	123.81 (15)
O3—C11—C7	129.01 (15)	C24—C28—C27	109.40 (14)
O3—C11—C10	117.60 (14)	C34—C29—C30	117.67 (15)
C7—C11—C10	113.39 (14)	C34—C29—C23	120.89 (13)
C13—C12—C17	117.47 (14)	C30—C29—C23	121.32 (14)
C13—C12—C6	123.65 (13)	C31—C30—C29	121.05 (17)
C17—C12—C6	118.87 (13)	C31—C30—H30A	119.5
C12—C13—C14	121.54 (15)	C29—C30—H30A	119.5
C12—C13—H13A	119.2	C32—C31—C30	119.64 (17)
C14—C13—H13A	119.2	C32—C31—H31A	120.2
C15—C14—C13	119.18 (16)	C30—C31—H31A	120.2
C15—C14—H14A	120.4	C31—C32—C33	121.00 (17)
C13—C14—H14A	120.4	C31—C32—Cl2	119.89 (16)
C14—C15—C16	120.89 (16)	C33—C32—Cl2	119.11 (17)
C14—C15—Cl1	119.41 (14)	C32—C33—C34	119.00 (18)
C16—C15—Cl1	119.70 (14)	C32—C33—H33A	120.5
C15—C16—C17	119.17 (16)	C34—C33—H33A	120.5
C15—C16—H16A	120.4	C33—C34—C29	121.64 (16)
C17—C16—H16A	120.4	C33—C34—H34A	119.2
C16—C17—C12	121.72 (16)	C29—C34—H34A	119.2

O1—C1—C2—C3	177.35 (18)	O5—C18—C19—C20	178.89 (19)
C5—C1—C2—C3	−2.3 (2)	C22—C18—C19—C20	−0.2 (2)
C1—C2—C3—C4	1.3 (2)	C18—C19—C20—C21	0.9 (2)
C2—C3—C4—O2	−179.42 (17)	C19—C20—C21—O6	−179.9 (2)
C2—C3—C4—C5	0.2 (2)	C19—C20—C21—C22	−1.3 (2)
O2—C4—C5—C1	177.93 (16)	O5—C18—C22—C21	−179.57 (19)
C3—C4—C5—C1	−1.6 (2)	C19—C18—C22—C21	−0.5 (2)
O2—C4—C5—C6	−4.9 (3)	O5—C18—C22—C23	−5.2 (3)
C3—C4—C5—C6	175.49 (15)	C19—C18—C22—C23	173.81 (17)
O1—C1—C5—C4	−177.19 (17)	O6—C21—C22—C18	179.83 (19)
C2—C1—C5—C4	2.5 (2)	C20—C21—C22—C18	1.1 (2)
O1—C1—C5—C6	5.8 (3)	O6—C21—C22—C23	4.8 (3)
C2—C1—C5—C6	−174.57 (15)	C20—C21—C22—C23	−173.88 (16)
C4—C5—C6—C7	110.93 (17)	C18—C22—C23—C24	72.4 (2)
C1—C5—C6—C7	−72.47 (19)	C21—C22—C23—C24	−113.89 (16)
C4—C5—C6—C12	−116.52 (16)	C18—C22—C23—C29	−57.9 (2)
C1—C5—C6—C12	60.1 (2)	C21—C22—C23—C29	115.82 (15)
C5—C6—C7—C11	60.0 (2)	C22—C23—C24—C25	119.43 (15)
C12—C6—C7—C11	−70.2 (2)	C29—C23—C24—C25	−109.75 (15)
C5—C6—C7—C8	−117.54 (14)	C22—C23—C24—C28	−66.24 (18)
C12—C6—C7—C8	112.20 (14)	C29—C23—C24—C28	64.58 (18)
C11—C7—C8—O4	−178.14 (14)	C28—C24—C25—O8	−179.23 (13)
C6—C7—C8—O4	−0.1 (2)	C23—C24—C25—O8	−4.0 (2)
C11—C7—C8—C9	1.64 (17)	C28—C24—C25—C26	0.67 (17)
C6—C7—C8—C9	179.73 (12)	C23—C24—C25—C26	175.88 (13)
O4—C8—C9—C10	177.76 (14)	O8—C25—C26—C27	179.57 (14)
C7—C8—C9—C10	−2.02 (17)	C24—C25—C26—C27	−0.33 (17)
C8—C9—C10—C11	1.57 (16)	C25—C26—C27—C28	−0.13 (16)
C8—C7—C11—O3	178.88 (15)	C25—C24—C28—O7	178.60 (16)
C6—C7—C11—O3	1.1 (3)	C23—C24—C28—O7	3.5 (3)
C8—C7—C11—C10	−0.56 (17)	C25—C24—C28—C27	−0.74 (17)
C6—C7—C11—C10	−178.35 (14)	C23—C24—C28—C27	−175.84 (14)
C9—C10—C11—O3	179.79 (14)	C26—C27—C28—O7	−178.84 (15)
C9—C10—C11—C7	−0.69 (18)	C26—C27—C28—C24	0.52 (17)
C7—C6—C12—C13	7.8 (2)	C24—C23—C29—C34	27.75 (18)
C5—C6—C12—C13	−124.24 (16)	C22—C23—C29—C34	159.21 (13)
C7—C6—C12—C17	−170.70 (13)	C24—C23—C29—C30	−156.14 (14)
C5—C6—C12—C17	57.23 (17)	C22—C23—C29—C30	−24.67 (19)
C17—C12—C13—C14	−1.2 (2)	C34—C29—C30—C31	−0.8 (2)
C6—C12—C13—C14	−179.74 (15)	C23—C29—C30—C31	−177.04 (15)
C12—C13—C14—C15	−0.4 (3)	C29—C30—C31—C32	0.3 (3)
C13—C14—C15—C16	1.6 (3)	C30—C31—C32—C33	0.7 (3)
C13—C14—C15—Cl1	−177.84 (14)	C30—C31—C32—Cl2	−179.82 (14)
C14—C15—C16—C17	−1.1 (3)	C31—C32—C33—C34	−1.1 (3)
Cl1—C15—C16—C17	178.33 (13)	Cl2—C32—C33—C34	179.40 (13)
C15—C16—C17—C12	−0.6 (3)	C32—C33—C34—C29	0.5 (2)
C13—C12—C17—C16	1.7 (2)	C30—C29—C34—C33	0.4 (2)
C6—C12—C17—C16	−179.68 (14)	C23—C29—C34—C33	176.63 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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−1/2, −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 formula	C₁₇H₁₅ClO₄
M_r	318.74
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	14.177 (2), 10.4002 (18), 21.347 (4)
β (°)	100.621 (2)
V (Å³)	3093.6 (9)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.36 × 0.19 × 0.13

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	21681, 5521, 4756
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.105, 1.03
No. of reflections	5521
No. of parameters	414
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.36

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O7	0.872 (16)	1.664 (17)	2.529 (2)	171 (3)
O3—H3···O1	0.869 (17)	1.701 (18)	2.558 (2)	169 (3)
O2—H2···O4ⁱ	0.858 (17)	1.688 (18)	2.5424 (16)	173 (3)
O8—H8···O6ⁱⁱ	0.856 (15)	1.708 (16)	2.5564 (16)	171 (2)
C9—H9A···O5ⁱⁱⁱ	0.97	2.52	3.277 (2)	134.4

Symmetry codes: (i) −x+2, y−1/2, −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

Allen, F. H., Lommerse, J. P. M., Hoy, V. J., Howard, J. A. K. & Desiraju, G. R. (1996). Acta Cryst. B52, 734–745. CrossRef CAS Web of Science IUCr Journals Google Scholar
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sutor, D. J. (1963). J. Chem. Soc. pp. 1105–1110. CrossRef Web of Science Google Scholar
Venkatesan, V., Fujii, A., Ebata, T. & Mikami, N. (2004). Chem. Phys. Lett. 394, 45–48. Web of Science CrossRef CAS Google Scholar
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. Google Scholar
Zhu, 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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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

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Experimental

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organic compounds

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