Tricyclo­[6.2.1.02,7]undeca-4,9-diene-3,6-dione

Wang, C.

doi:10.1107/S1600536808030249

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page o2002

doi:10.1107/S1600536808030249

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Tricyclo[6.2.1.0^2,7]undeca-4,9-diene-3,6-dione

Chongchen Wang ^a ^*

^aSchool of Environment and Energy Engineering, Beijing University of Civil Engineering and Architecture, 100044 Beijing, People's Republic of China
^*Correspondence e-mail: chongchenwang@126.com

(Received 8 September 2008; accepted 19 September 2008; online 24 September 2008)

The title compound, C₁₁H₁₀O₂, crystallizes with two independent molecules in the asymmetric unit. In one molecule, the dihedral angle between the mean planes of the C—C=C—C group of the diene unit and essentially planar cyclohexene ring is 51.07 (9)°, while in the other molecule it is 54.49 (12)°. In the crystal structure, weak intermolecular C—H⋯O interactions link the molecules into columns along the b axis.

Related literature

For background information, see: Ito et al. (2007 ); Mgani et al. (1995 ).

Experimental

Crystal data

C₁₁H₁₀O₂
M_r = 174.19
Monoclinic, P 2₁ /c
a = 15.649 (3) Å
b = 6.5399 (13) Å
c = 21.448 (7) Å
β = 125.05 (2)°
V = 1797.0 (8) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 (2) K
0.52 × 0.12 × 0.11 mm

Data collection

Rigaku R-AXIS RAPID IP area-detector diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.956, T_max = 0.990
6936 measured reflections
4119 independent reflections
2664 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.066
wR(F²) = 0.210
S = 1.03
4119 reflections
251 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O4ⁱ	0.93	2.58	3.502 (3)	172
C6—H6A⋯O2ⁱⁱ	0.98	2.53	3.446 (3)	155
C11—H11A⋯O3ⁱⁱⁱ	0.93	2.58	3.335 (4)	138
C16—H16A⋯O1ⁱ	0.98	2.59	3.416 (3)	142
C17—H17A⋯O4^iv	0.98	2.51	3.319 (3)	140
Symmetry codes: (i) -x+1, -y, -z; (ii) x, y+1, z; (iii) $[x, -y-{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iv) x, y-1, z.

Data collection: RAPID-AUTO (Rigaku, 2001 ); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808030249/lh2695sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808030249/lh2695Isup2.hkl

checkCIF report

Comment top

The title compound, tricyclo[6.2.1.0^2,7]undeca-4,9-diene-3,6 -dione formed by the cycloaddition between cyclopentadiene and p-benzoquinone has been investigated widely ( Ito et al. 2007; Mgani, et al. 1995). One of the unique aspect of the title compound is its high molecular symmetry, which allows for facile selective reactions at one or both carbonyl groups by means of classical and non-classical reagents. Another feature to be considered is its cage-like framework, which forces functional groups into close spatial proximity, facilitating subsequent reactions (Ito et al. 2007).

The title compound crystallizes with two independent molecules in the asymmetric unit, as shown in Fig.1. In one molecule, the dihedral angle between the mean planes of C-C=C-C group of the diene unit and essentially planar cyclohexene ring is [C1-C6] 51.07 (9)° while in the other [C12-C17] it is 54.49 (12)°. In the crystal structure, weak intermolecular C—H···O interactions link the molecules into columns along the b-axis (Fig .2).

Related literature top

For background information, see: Ito et al. (2007); Mgani et al. (1995).

Experimental top

Tricyclo[6.2.1.0^2,7]undeca-4,9-diene-3,6-dione was obtained by the method described in the literature (Ito et al. 2007). The crystals of the title compound was recrystallized from hexane under low temperature (273.15 K).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2001); cell refinement: RAPID-AUTO (Rigaku, 2001); data reduction: RAPID-AUTO (Rigaku, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of the title compound, showing atoms labelling. Displacement ellipoids are drawn at the 50% probability level.
	Fig. 2. Packing diagram.

Tricyclo[6.2.1.0^2,7]undeca-4,9-diene-3,6-dione top

Crystal data top

C₁₁H₁₀O₂	F(000) = 736
M_r = 174.19	D_x = 1.288 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 16732 reflections
a = 15.649 (3) Å	θ = 1.6–27.5°
b = 6.5399 (13) Å	µ = 0.09 mm⁻¹
c = 21.448 (7) Å	T = 293 K
β = 125.05 (2)°	Needle, dark brown
V = 1797.0 (8) Å³	0.52 × 0.12 × 0.11 mm
Z = 8

Data collection top

Rigaku R-AXIS RAPID IP area-detector diffractometer	4119 independent reflections
Radiation source: Rotating Anode	2664 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
ω oscillation scans	θ_max = 27.5°, θ_min = 1.6°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −20→20
T_min = 0.956, T_max = 0.990	k = −8→8
6936 measured reflections	l = −27→27

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.210	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.118P)² + 0.1983P] where P = (F_o² + 2F_c²)/3
4119 reflections	(Δ/σ)_max < 0.001
251 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₁H₁₀O₂	V = 1797.0 (8) Å³
M_r = 174.19	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.649 (3) Å	µ = 0.09 mm⁻¹
b = 6.5399 (13) Å	T = 293 K
c = 21.448 (7) Å	0.52 × 0.12 × 0.11 mm
β = 125.05 (2)°

Data collection top

Rigaku R-AXIS RAPID IP area-detector diffractometer	4119 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2664 reflections with I > 2σ(I)
T_min = 0.956, T_max = 0.990	R_int = 0.036
6936 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.066	0 restraints
wR(F²) = 0.210	H-atom parameters constrained
S = 1.03	Δρ_max = 0.22 e Å⁻³
4119 reflections	Δρ_min = −0.21 e Å⁻³
251 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
O1	0.29192 (15)	0.0348 (3)	0.02418 (12)	0.0946 (7)
O2	0.1016 (2)	−0.5875 (3)	−0.16845 (10)	0.1029 (8)
C1	0.23966 (16)	−0.1048 (3)	−0.01874 (12)	0.0551 (5)
C2	0.28081 (17)	−0.3137 (4)	−0.00061 (13)	0.0596 (6)
H2A	0.3425	−0.3397	0.0467	0.074 (7)*
C3	0.23343 (19)	−0.4665 (4)	−0.04914 (13)	0.0616 (6)
H3A	0.2631	−0.5960	−0.0342	0.080 (8)*
C4	0.13635 (19)	−0.4419 (4)	−0.12469 (12)	0.0581 (6)
C5	0.07944 (16)	−0.2423 (3)	−0.14694 (10)	0.0490 (5)
H5A	0.0655	−0.1990	−0.1957	0.067 (7)*
C6	0.13399 (15)	−0.0649 (3)	−0.08969 (11)	0.0478 (5)
H6A	0.1391	0.0514	−0.1162	0.066 (7)*
C7	0.05338 (18)	−0.0092 (4)	−0.07124 (13)	0.0638 (7)
H7A	0.0633	0.1236	−0.0468	0.082 (8)*
C8	−0.04733 (19)	−0.0353 (5)	−0.15063 (15)	0.0781 (8)
H8A	−0.1095	−0.0148	−0.1516	0.111 (11)*
H8B	−0.0497	0.0498	−0.1886	0.082 (8)*
C9	−0.02716 (19)	−0.2589 (5)	−0.15655 (14)	0.0706 (7)
H9A	−0.0828	−0.3311	−0.2022	0.096 (9)*
C10	−0.0019 (2)	−0.3395 (5)	−0.08217 (17)	0.0799 (8)
H10A	−0.0175	−0.4691	−0.0735	0.096*
C11	0.0467 (2)	−0.1914 (5)	−0.03133 (15)	0.0760 (8)
H11A	0.0721	−0.1986	0.0199	0.091*
O3	0.2497 (2)	−0.2686 (4)	−0.34967 (12)	0.1181 (10)
O4	0.48892 (15)	0.3614 (3)	−0.18269 (12)	0.0870 (6)
C12	0.3043 (2)	−0.1294 (4)	−0.30817 (13)	0.0652 (6)
C13	0.28648 (19)	0.0779 (4)	−0.33792 (13)	0.0656 (6)
H13A	0.2323	0.1012	−0.3886	0.092 (9)*
C14	0.34485 (18)	0.2354 (4)	−0.29597 (14)	0.0620 (6)
H14A	0.3289	0.3645	−0.3182	0.082 (9)*
C15	0.43306 (16)	0.2141 (3)	−0.21624 (13)	0.0541 (5)
C16	0.45436 (15)	0.0118 (3)	−0.17730 (11)	0.0504 (5)
H16A	0.5278	−0.0221	−0.1540	0.050 (6)*
C17	0.38776 (16)	−0.1714 (3)	−0.22614 (11)	0.0511 (5)
H17A	0.4348	−0.2753	−0.2236	0.066 (7)*
C18	0.34259 (19)	−0.2549 (4)	−0.18255 (14)	0.0665 (7)
H18A	0.3164	−0.3956	−0.1948	0.070 (7)*
C19	0.4353 (2)	−0.2168 (5)	−0.10083 (14)	0.0796 (8)
H19A	0.4984	−0.2847	−0.0886	0.083 (9)*
H19B	0.4212	−0.2508	−0.0636	0.129 (13)*
C20	0.4363 (2)	0.0123 (5)	−0.11275 (13)	0.0755 (8)
H20A	0.4863	0.0923	−0.0673	0.085 (8)*
C21	0.3220 (3)	0.0601 (6)	−0.15010 (19)	0.0928 (10)
H21A	0.2952	0.1807	−0.1449	0.111*
C22	0.2675 (2)	−0.0992 (5)	−0.19120 (19)	0.0837 (9)
H22A	0.1953	−0.1120	−0.2203	0.100*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0699 (12)	0.0600 (11)	0.0883 (13)	−0.0093 (9)	0.0071 (10)	−0.0161 (10)
O2	0.152 (2)	0.0603 (12)	0.0557 (11)	0.0017 (12)	0.0360 (12)	−0.0137 (9)
C1	0.0451 (11)	0.0487 (12)	0.0563 (12)	−0.0051 (9)	0.0203 (10)	−0.0048 (10)
C2	0.0436 (11)	0.0587 (14)	0.0559 (12)	0.0071 (10)	0.0165 (10)	0.0076 (11)
C3	0.0689 (14)	0.0461 (13)	0.0621 (13)	0.0107 (10)	0.0332 (12)	0.0048 (10)
C4	0.0789 (15)	0.0498 (13)	0.0433 (10)	−0.0029 (10)	0.0337 (11)	−0.0023 (9)
C5	0.0531 (11)	0.0533 (12)	0.0338 (9)	−0.0004 (9)	0.0210 (8)	0.0037 (8)
C6	0.0473 (11)	0.0420 (11)	0.0495 (10)	0.0025 (8)	0.0252 (9)	0.0044 (9)
C7	0.0566 (13)	0.0709 (16)	0.0573 (12)	0.0184 (11)	0.0290 (11)	−0.0016 (11)
C8	0.0511 (14)	0.107 (2)	0.0661 (15)	0.0232 (14)	0.0278 (12)	0.0209 (15)
C9	0.0462 (12)	0.091 (2)	0.0531 (12)	−0.0129 (12)	0.0158 (10)	0.0009 (13)
C10	0.0608 (15)	0.099 (2)	0.0882 (19)	−0.0061 (14)	0.0478 (15)	0.0189 (17)
C11	0.0644 (15)	0.116 (2)	0.0589 (14)	0.0220 (15)	0.0421 (13)	0.0195 (15)
O3	0.140 (2)	0.0854 (15)	0.0597 (11)	−0.0461 (14)	0.0168 (12)	−0.0131 (10)
O4	0.0699 (11)	0.0565 (11)	0.0983 (14)	−0.0123 (9)	0.0271 (10)	−0.0112 (10)
C12	0.0673 (14)	0.0638 (16)	0.0458 (11)	−0.0136 (11)	0.0216 (11)	−0.0050 (10)
C13	0.0593 (13)	0.0700 (16)	0.0463 (12)	0.0002 (11)	0.0179 (10)	0.0078 (11)
C14	0.0592 (13)	0.0550 (14)	0.0658 (13)	0.0049 (10)	0.0323 (12)	0.0107 (11)
C15	0.0439 (11)	0.0511 (13)	0.0637 (13)	−0.0030 (9)	0.0288 (10)	−0.0090 (10)
C16	0.0380 (10)	0.0581 (13)	0.0476 (10)	0.0017 (8)	0.0201 (9)	−0.0036 (9)
C17	0.0529 (11)	0.0498 (12)	0.0485 (11)	0.0011 (9)	0.0279 (9)	−0.0009 (9)
C18	0.0641 (14)	0.0672 (16)	0.0671 (14)	−0.0060 (12)	0.0370 (12)	0.0097 (12)
C19	0.0854 (19)	0.099 (2)	0.0553 (14)	0.0059 (16)	0.0409 (14)	0.0162 (14)
C20	0.0889 (19)	0.089 (2)	0.0512 (13)	−0.0114 (15)	0.0418 (13)	−0.0153 (13)
C21	0.123 (3)	0.095 (2)	0.113 (2)	0.024 (2)	0.098 (2)	0.005 (2)
C22	0.0706 (17)	0.098 (2)	0.104 (2)	0.0038 (16)	0.0628 (17)	0.0162 (19)

Geometric parameters (Å, º) top

O1—C1	1.219 (3)	O3—C12	1.215 (3)
O2—C4	1.224 (3)	O4—C15	1.220 (3)
C1—C2	1.464 (3)	C12—C13	1.456 (4)
C1—C6	1.493 (3)	C12—C17	1.496 (3)
C2—C3	1.321 (3)	C13—C14	1.327 (3)
C2—H2A	0.9301	C13—H13A	0.9300
C3—C4	1.460 (3)	C14—C15	1.462 (3)
C3—H3A	0.9299	C14—H14A	0.9300
C4—C5	1.495 (3)	C15—C16	1.497 (3)
C5—C6	1.542 (3)	C16—C17	1.538 (3)
C5—C9	1.563 (3)	C16—C20	1.564 (3)
C5—H5A	0.9799	C16—H16A	0.9800
C6—C7	1.567 (3)	C17—C18	1.559 (3)
C6—H6A	0.9800	C17—H17A	0.9800
C7—C11	1.505 (4)	C18—C22	1.483 (4)
C7—C8	1.526 (3)	C18—C19	1.523 (4)
C7—H7A	0.9800	C18—H18A	0.9800
C8—C9	1.517 (4)	C19—C20	1.522 (4)
C8—H8A	0.9702	C19—H19A	0.9700
C8—H8B	0.9700	C19—H19B	0.9700
C9—C10	1.502 (4)	C20—C21	1.514 (4)
C9—H9A	0.9801	C20—H20A	0.9801
C10—C11	1.324 (4)	C21—C22	1.314 (4)
C10—H10A	0.9300	C21—H21A	0.9300
C11—H11A	0.9300	C22—H22A	0.9300

O1—C1—C2	119.8 (2)	O3—C12—C13	120.0 (2)
O1—C1—C6	120.6 (2)	O3—C12—C17	119.7 (2)
C2—C1—C6	119.63 (18)	C13—C12—C17	120.3 (2)
C3—C2—C1	122.3 (2)	C14—C13—C12	122.8 (2)
C3—C2—H2A	118.8	C14—C13—H13A	118.4
C1—C2—H2A	118.9	C12—C13—H13A	118.8
C2—C3—C4	123.1 (2)	C13—C14—C15	122.6 (2)
C2—C3—H3A	118.3	C13—C14—H14A	118.7
C4—C3—H3A	118.6	C15—C14—H14A	118.7
O2—C4—C3	119.1 (2)	O4—C15—C14	119.4 (2)
O2—C4—C5	120.9 (2)	O4—C15—C16	121.0 (2)
C3—C4—C5	120.00 (19)	C14—C15—C16	119.67 (19)
C4—C5—C6	116.52 (17)	C15—C16—C17	117.52 (17)
C4—C5—C9	112.11 (19)	C15—C16—C20	113.36 (19)
C6—C5—C9	102.60 (18)	C17—C16—C20	102.03 (18)
C4—C5—H5A	108.6	C15—C16—H16A	107.7
C6—C5—H5A	108.3	C17—C16—H16A	108.0
C9—C5—H5A	108.3	C20—C16—H16A	107.8
C1—C6—C5	117.58 (17)	C12—C17—C16	116.78 (19)
C1—C6—C7	111.38 (18)	C12—C17—C18	112.29 (19)
C5—C6—C7	102.61 (17)	C16—C17—C18	103.15 (17)
C1—C6—H6A	108.4	C12—C17—H17A	108.2
C5—C6—H6A	108.3	C16—C17—H17A	108.0
C7—C6—H6A	108.1	C18—C17—H17A	108.0
C11—C7—C8	100.5 (2)	C22—C18—C19	101.2 (2)
C11—C7—C6	106.78 (19)	C22—C18—C17	106.5 (2)
C8—C7—C6	99.07 (18)	C19—C18—C17	99.93 (19)
C11—C7—H7A	116.0	C22—C18—H18A	115.5
C8—C7—H7A	116.2	C19—C18—H18A	115.9
C6—C7—H7A	116.0	C17—C18—H18A	115.6
C9—C8—C7	94.01 (19)	C20—C19—C18	93.6 (2)
C9—C8—H8A	112.7	C20—C19—H19A	112.9
C7—C8—H8A	112.9	C18—C19—H19A	112.7
C9—C8—H8B	113.1	C20—C19—H19B	113.1
C7—C8—H8B	112.9	C18—C19—H19B	113.2
H8A—C8—H8B	110.4	H19A—C19—H19B	110.5
C10—C9—C8	100.9 (2)	C21—C20—C19	99.8 (3)
C10—C9—C5	105.94 (19)	C21—C20—C16	106.9 (2)
C8—C9—C5	100.4 (2)	C19—C20—C16	99.8 (2)
C10—C9—H9A	115.7	C21—C20—H20A	116.2
C8—C9—H9A	116.1	C19—C20—H20A	116.0
C5—C9—H9A	115.7	C16—C20—H20A	115.8
C11—C10—C9	107.1 (3)	C22—C21—C20	107.8 (3)
C11—C10—H10A	126.4	C22—C21—H21A	126.1
C9—C10—H10A	126.4	C20—C21—H21A	126.1
C10—C11—C7	107.8 (2)	C21—C22—C18	107.4 (3)
C10—C11—H11A	126.1	C21—C22—H22A	126.3
C7—C11—H11A	126.1	C18—C22—H22A	126.3

O1—C1—C2—C3	−171.7 (3)	O3—C12—C13—C14	−178.5 (3)
C6—C1—C2—C3	8.3 (4)	C17—C12—C13—C14	3.1 (4)
C1—C2—C3—C4	−0.1 (4)	C12—C13—C14—C15	0.7 (4)
C2—C3—C4—O2	174.5 (3)	C13—C14—C15—O4	173.9 (3)
C2—C3—C4—C5	−7.1 (4)	C13—C14—C15—C16	−5.3 (4)
O2—C4—C5—C6	−175.9 (2)	O4—C15—C16—C17	−173.3 (2)
C3—C4—C5—C6	5.7 (3)	C14—C15—C16—C17	5.9 (3)
O2—C4—C5—C9	66.3 (3)	O4—C15—C16—C20	68.0 (3)
C3—C4—C5—C9	−112.1 (2)	C14—C15—C16—C20	−112.8 (2)
O1—C1—C6—C5	171.2 (2)	O3—C12—C17—C16	179.5 (3)
C2—C1—C6—C5	−8.9 (3)	C13—C12—C17—C16	−2.1 (3)
O1—C1—C6—C7	−70.9 (3)	O3—C12—C17—C18	−61.7 (3)
C2—C1—C6—C7	109.1 (2)	C13—C12—C17—C18	116.7 (3)
C4—C5—C6—C1	2.1 (3)	C15—C16—C17—C12	−2.3 (3)
C9—C5—C6—C1	124.9 (2)	C20—C16—C17—C12	122.3 (2)
C4—C5—C6—C7	−120.51 (19)	C15—C16—C17—C18	−125.9 (2)
C9—C5—C6—C7	2.3 (2)	C20—C16—C17—C18	−1.3 (2)
C1—C6—C7—C11	−61.5 (2)	C12—C17—C18—C22	−57.7 (3)
C5—C6—C7—C11	65.1 (2)	C16—C17—C18—C22	68.9 (2)
C1—C6—C7—C8	−165.4 (2)	C12—C17—C18—C19	−162.6 (2)
C5—C6—C7—C8	−38.8 (2)	C16—C17—C18—C19	−36.0 (2)
C11—C7—C8—C9	−49.1 (2)	C22—C18—C19—C20	−50.3 (2)
C6—C7—C8—C9	60.0 (2)	C17—C18—C19—C20	58.9 (2)
C7—C8—C9—C10	49.8 (2)	C18—C19—C20—C21	49.3 (2)
C7—C8—C9—C5	−58.9 (2)	C18—C19—C20—C16	−59.9 (2)
C4—C5—C9—C10	56.3 (3)	C15—C16—C20—C21	62.2 (3)
C6—C5—C9—C10	−69.4 (3)	C17—C16—C20—C21	−65.2 (3)
C4—C5—C9—C8	160.98 (18)	C15—C16—C20—C19	165.6 (2)
C6—C5—C9—C8	35.2 (2)	C17—C16—C20—C19	38.3 (2)
C8—C9—C10—C11	−33.6 (3)	C19—C20—C21—C22	−33.2 (3)
C5—C9—C10—C11	70.6 (3)	C16—C20—C21—C22	70.3 (3)
C9—C10—C11—C7	0.7 (3)	C20—C21—C22—C18	0.0 (3)
C8—C7—C11—C10	32.2 (3)	C19—C18—C22—C21	33.3 (3)
C6—C7—C11—C10	−70.7 (3)	C17—C18—C22—C21	−70.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O4ⁱ	0.93	2.58	3.502 (3)	172
C6—H6A···O2ⁱⁱ	0.98	2.53	3.446 (3)	155
C11—H11A···O3ⁱⁱⁱ	0.93	2.58	3.335 (4)	138
C16—H16A···O1ⁱ	0.98	2.59	3.416 (3)	142
C17—H17A···O4^iv	0.98	2.51	3.319 (3)	140

Symmetry codes: (i) −x+1, −y, −z; (ii) x, y+1, z; (iii) x, −y−1/2, z+1/2; (iv) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₀O₂
M_r	174.19
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	15.649 (3), 6.5399 (13), 21.448 (7)
β (°)	125.05 (2)
V (Å³)	1797.0 (8)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.52 × 0.12 × 0.11

Data collection
Diffractometer	Rigaku R-AXIS RAPID IP area-detector diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.956, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	6936, 4119, 2664
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.066, 0.210, 1.03
No. of reflections	4119
No. of parameters	251
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.21

Computer programs: RAPID-AUTO (Rigaku, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O4ⁱ	0.93	2.58	3.502 (3)	172
C6—H6A···O2ⁱⁱ	0.98	2.53	3.446 (3)	155
C11—H11A···O3ⁱⁱⁱ	0.93	2.58	3.335 (4)	138
C16—H16A···O1ⁱ	0.98	2.59	3.416 (3)	142
C17—H17A···O4^iv	0.98	2.51	3.319 (3)	140

Symmetry codes: (i) −x+1, −y, −z; (ii) x, y+1, z; (iii) x, −y−1/2, z+1/2; (iv) x, y−1, z.

Acknowledgements

The author gratefully acknowledges financial support by the Beijing Academic Innovation Group in Sustainable Water/Waste Recycling Technologies (grant No. BJE10016200611), the Research Fund of Beijing University of Civil Engineering and Architecture (grant No. 100700502) and the Funding Project for Academic Human Resources Development in Institutions of Higher Learning Under the Jurisdiction of Beijing Municipality (grant No. BJE10016200611).

References

Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Ito, F. M., Petroni, J. M., de Lima, D. P., Beatriz, A., Marques, M. R., de Moraes, M. O., Costa-Lotufo, L. V., Montenegro, R. C., Magalhães, H. I. F., do, Ó. & Pessoa, C. (2007). Molecules, 12, 271–282. Web of Science CrossRef PubMed CAS Google Scholar
Mgani, Q. A., Nkunya, M., Zwanenburg, B. & Klunder, A. (1995). Tetrahedron Lett. 26, 4661–4664. CrossRef Web of Science Google Scholar
Rigaku (2001). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar