(4aR,9R,9aR)-7-Bromo-9-nitro­methyl-2,3,4,4a,9,9a-hexa­hydro-1H-xanthen-1-one

Wu, C.; Guo, Y.-J.; Xia, A.-B.

doi:10.1107/S1600536813008659

organic compounds

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ISSN: 2056-9890

Volume 69| Part 5| May 2013| Page o794

https://doi.org/10.1107/S1600536813008659

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(4aR,9R,9aR)-7-Bromo-9-nitromethyl-2,3,4,4a,9,9a-hexahydro-1H-xanthen-1-one

Chao Wu,^a Yan-Jun Guo ^a and Ai-Bao Xia ^a ^*

^aState Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China
^*Correspondence e-mail: xiaaibao@zjut.edu.cn

(Received 19 February 2013; accepted 29 March 2013; online 27 April 2013)

The title compound, C₁₄H₁₄BrNO₄, contains a tricyclic ring system including three contiguous stereocenters all of which exhibit an R configuration. The cyclohexanone ring adopts a chair conformation. The central oxane ring assumes a strained envelope conformation, with five of the ring atoms being nearly coplanar with the bromophenyl group and with the C atom adjacent to the O atom and fused with the cyclohexanone ring as the flap. In the crystal, molecules are linked into a three-dimensional network by C—H⋯O interactions.

Related literature

For related structures, see: Shi et al. (2004 ); Xia et al. (2009 ); Ndjakou Lenta et al. (2007 ). For background information on domino reactions, see Enders et al. (2007 ); Yu & Wang (2002 ).

Experimental

Crystal data

C₁₄H₁₄BrNO₄
M_r = 340.17
Monoclinic, P 2₁
a = 10.3457 (7) Å
b = 5.4662 (5) Å
c = 13.2446 (12) Å
β = 102.849 (2)°
V = 730.25 (11) Å³
Z = 2
Mo Kα radiation
μ = 2.83 mm⁻¹
T = 296 K
0.53 × 0.47 × 0.14 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.224, T_max = 0.673
6335 measured reflections
2655 independent reflections
1537 reflections with I > 2σ(I)
R_int = 0.061

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.137
S = 1.00
2655 reflections
181 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.46 e Å⁻³
Absolute structure: Flack (1983 ), 1058 Friedel pairs
Flack parameter: 0.021 (17)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O1ⁱ	0.93	2.71	3.520 (9)	146
C8—H8B⋯O2ⁱⁱ	0.97	2.59	3.489 (6)	155
C8—H8A⋯O4ⁱⁱⁱ	0.97	2.54	3.253 (4)	131
C10—H10⋯O2^iv	0.98	2.53	3.300 (8)	135
C11—H11⋯O3^v	0.98	2.59	3.547 (8)	165
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+1]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z]$ ; (iii) $[-x+1, y+{\script{1\over 2}}, -z]$ ; (iv) x, y-1, z; (v) x, y+1, z.

Data collection: PROCESS-AUTO (Rigaku, 2006 ); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku, 2007 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: WinGX (Farrugia, 2012).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536813008659/fy2090sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813008659/fy2090Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813008659/fy2090Isup3.cml

checkCIF report

Comment top

Domino or cascade reactions, in which multiple new bonds and stereocenters could be formed, have been getting more interest in asymmetric organocatalysis (Enders et al., 2007; Yu et al., 2002) . The title compound, (I), was synthesized as one of a series of oxa-Michael-Michael products under investigation.

In this paper, the crystal of title compound (4aR,9R,9aR)-7-bromo-9- (nitromethyl)-2,3,4,4a,9,9a-hexahydro-1H-xanthen-1-one was determined. The structure of (I) is shown in Fig. 1. The O1—C4 bond and the bromophenyl group are almost coplanar: the angle is 3.2 (6) ° between the plane of the bromophenyl ring and the O1—C4—C12 plane. The C11—C12 bond and the bromophenyl plane enclose an angle of 9.4 (7) °. The cyclohexanone ring (C5—C6—C7—C8—C9—C10) adopts a chair conformation. The conformation of the oxane ring is nonstandard. Five atoms of the oxane ring are coplanar with the bromophenyl group and only C5 deviates significantly from the common plane.

Related literature top

For related structures, see: Shi et al. (2004); Xia et al. (2009); Ndjakou Lenta et al. (2007). For background information on domino reactions, see Enders et al. (2007); Yu & Wang (2002).

Experimental top

To the solution of the catalyst (S)-2-(pyrrolidin-2-ylmethylthio)pyridine (20 mol%) and 4-(trifluoromethyl)benzoic acid (10 mol%) in saturated aqueous NaCl (0.25 ml) was added sequentially cyclohexenone (0.8 mmol) and (E)-4-bromo-2-(2-nitrovinyl)phenol (0.2 mmol) at room temperature with vigorous stirring. After completion, the reaction mixture was extracted with EtOAc (3*10 ml), washed with water, dried and concentrated. The residue was purified by flash chromatography to the product. Then, suitable crystals of the title compound were obtained by slow evaporation of methanol solution at room temperature.

Structure description top

For related structures, see: Shi et al. (2004); Xia et al. (2009); Ndjakou Lenta et al. (2007). For background information on domino reactions, see Enders et al. (2007); Yu & Wang (2002).

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 2006); cell refinement: PROCESS-AUTO (Rigaku, 2006); data reduction: CrystalStructure (Rigaku, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top

	Fig. 1. The asymmetric unit of the structure of the title compound, with the atomic labeling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Unit cell packing of the title compound.

(4aR,9R,9aR)-7-Bromo-9-nitromethyl-2,3,4,4a,9,9a-hexahydro-1H-xanthen-1-one top

Crystal data top

C₁₄H₁₄BrNO₄	F(000) = 344
M_r = 340.17	D_x = 1.547 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 4391 reflections
a = 10.3457 (7) Å	θ = 3.2–27.4°
b = 5.4662 (5) Å	µ = 2.83 mm⁻¹
c = 13.2446 (12) Å	T = 296 K
β = 102.849 (2)°	Platelet, colorless
V = 730.25 (11) Å³	0.53 × 0.47 × 0.14 mm
Z = 2

Data collection top

Rigaku R-AXIS RAPID diffractometer	2655 independent reflections
Radiation source: rotating anode	1537 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.061
Detector resolution: 10.00 pixels mm^-1	θ_max = 26.0°, θ_min = 3.2°
ω scans	h = −12→12
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −6→6
T_min = 0.224, T_max = 0.673	l = −16→16
6335 measured reflections

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)] = 0.052	H-atom parameters constrained
wR(F²) = 0.137	w = 1/[σ²(F_o²) + (0.0525P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
2655 reflections	Δρ_max = 0.36 e Å⁻³
181 parameters	Δρ_min = −0.46 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1058 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.021 (17)

Crystal data top

C₁₄H₁₄BrNO₄	V = 730.25 (11) Å³
M_r = 340.17	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 10.3457 (7) Å	µ = 2.83 mm⁻¹
b = 5.4662 (5) Å	T = 296 K
c = 13.2446 (12) Å	0.53 × 0.47 × 0.14 mm
β = 102.849 (2)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	2655 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	1537 reflections with I > 2σ(I)
T_min = 0.224, T_max = 0.673	R_int = 0.061
6335 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	H-atom parameters constrained
wR(F²) = 0.137	Δρ_max = 0.36 e Å⁻³
S = 1.00	Δρ_min = −0.46 e Å⁻³
2655 reflections	Absolute structure: Flack (1983), 1058 Friedel pairs
181 parameters	Absolute structure parameter: 0.021 (17)
1 restraint

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
C1	0.1121 (7)	0.9599 (12)	0.3568 (5)	0.0740 (18)
C2	0.2242 (7)	0.9776 (13)	0.4388 (6)	0.084 (2)
H2	0.2201	1.0658	0.4980	0.101*
C3	0.3408 (7)	0.8631 (13)	0.4308 (5)	0.079 (2)
H3	0.4154	0.8757	0.4847	0.095*
C4	0.3469 (5)	0.7291 (10)	0.3426 (5)	0.0575 (14)
C5	0.4665 (5)	0.4397 (10)	0.2629 (5)	0.0594 (15)
H5	0.4212	0.2917	0.2785	0.071*
C6	0.6112 (5)	0.3829 (12)	0.2656 (6)	0.074 (2)
H6A	0.6535	0.3222	0.3337	0.089*
H6B	0.6160	0.2555	0.2156	0.089*
C7	0.6840 (5)	0.6043 (15)	0.2415 (5)	0.0816 (19)
H7A	0.7741	0.5588	0.2397	0.098*
H7B	0.6882	0.7244	0.2960	0.098*
C8	0.6170 (5)	0.7183 (13)	0.1378 (6)	0.077 (2)
H8A	0.6599	0.8722	0.1292	0.092*
H8B	0.6273	0.6101	0.0820	0.092*
C9	0.4716 (5)	0.7627 (10)	0.1311 (4)	0.0553 (14)
C10	0.3944 (4)	0.5445 (8)	0.1576 (4)	0.0461 (12)
H10	0.3945	0.4183	0.1050	0.055*
C11	0.2504 (4)	0.6049 (10)	0.1573 (4)	0.0487 (12)
H11	0.2196	0.7266	0.1029	0.058*
C12	0.2391 (5)	0.7152 (9)	0.2586 (5)	0.0518 (14)
C13	0.1217 (6)	0.8341 (11)	0.2703 (5)	0.0650 (16)
H13	0.0473	0.8255	0.2160	0.078*
C14	0.1623 (5)	0.3767 (10)	0.1314 (5)	0.0572 (15)
H14A	0.2038	0.2403	0.1732	0.069*
H14B	0.0773	0.4073	0.1485	0.069*
N1	0.1410 (4)	0.3111 (10)	0.0188 (5)	0.0621 (14)
O1	0.4667 (3)	0.6210 (10)	0.3413 (3)	0.0647 (10)
O2	0.4213 (4)	0.9576 (7)	0.1075 (4)	0.0745 (13)
O3	0.1104 (4)	0.0988 (9)	−0.0041 (4)	0.1026 (17)
O4	0.1497 (5)	0.4689 (10)	−0.0439 (4)	0.0874 (14)
Br1	−0.04348 (7)	1.1196 (2)	0.36550 (7)	0.1208 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.094 (4)	0.080 (4)	0.048 (5)	0.010 (3)	0.015 (4)	−0.003 (4)
C2	0.096 (5)	0.101 (5)	0.057 (5)	0.017 (4)	0.022 (4)	−0.021 (4)
C3	0.091 (5)	0.100 (5)	0.042 (4)	0.014 (4)	0.003 (3)	−0.012 (4)
C4	0.064 (3)	0.065 (3)	0.044 (4)	0.008 (3)	0.015 (3)	0.007 (3)
C5	0.063 (3)	0.065 (3)	0.050 (4)	0.008 (3)	0.011 (3)	0.009 (3)
C6	0.045 (3)	0.093 (4)	0.078 (5)	0.008 (3)	−0.002 (3)	−0.024 (4)
C7	0.046 (3)	0.098 (5)	0.096 (5)	0.001 (4)	0.004 (3)	−0.019 (5)
C8	0.069 (4)	0.080 (4)	0.087 (6)	0.000 (3)	0.029 (4)	−0.008 (4)
C9	0.066 (3)	0.061 (4)	0.037 (4)	−0.004 (3)	0.008 (3)	−0.005 (3)
C10	0.053 (2)	0.047 (3)	0.039 (3)	0.000 (2)	0.011 (2)	−0.009 (2)
C11	0.057 (2)	0.044 (2)	0.044 (3)	−0.002 (3)	0.009 (2)	0.005 (3)
C12	0.053 (3)	0.054 (3)	0.050 (4)	0.003 (2)	0.013 (2)	0.006 (2)
C13	0.070 (3)	0.066 (4)	0.059 (5)	−0.001 (3)	0.013 (3)	0.010 (3)
C14	0.047 (3)	0.056 (3)	0.069 (5)	−0.006 (2)	0.013 (3)	0.001 (3)
N1	0.037 (2)	0.072 (3)	0.073 (4)	0.011 (2)	0.002 (2)	−0.010 (3)
O1	0.063 (2)	0.086 (2)	0.040 (2)	0.016 (2)	0.0012 (16)	−0.008 (2)
O2	0.084 (3)	0.056 (2)	0.083 (4)	−0.013 (2)	0.017 (2)	0.011 (2)
O3	0.097 (3)	0.070 (3)	0.123 (4)	−0.004 (3)	−0.015 (3)	−0.040 (3)
O4	0.104 (3)	0.105 (4)	0.052 (3)	−0.013 (3)	0.013 (3)	−0.012 (3)
Br1	0.1011 (5)	0.1479 (8)	0.1168 (8)	0.0504 (6)	0.0314 (5)	−0.0231 (7)

Geometric parameters (Å, º) top

C1—C13	1.359 (9)	C7—H7B	0.9700
C1—C2	1.405 (9)	C8—C9	1.506 (8)
C1—Br1	1.857 (6)	C8—H8A	0.9700
C2—C3	1.383 (8)	C8—H8B	0.9700
C2—H2	0.9300	C9—O2	1.196 (6)
C3—C4	1.393 (8)	C9—C10	1.519 (7)
C3—H3	0.9300	C10—C11	1.525 (6)
C4—O1	1.376 (6)	C10—H10	0.9800
C4—C12	1.391 (7)	C11—C12	1.499 (7)
C5—O1	1.435 (8)	C11—C14	1.538 (7)
C5—C6	1.521 (7)	C11—H11	0.9800
C5—C10	1.538 (8)	C12—C13	1.417 (7)
C5—H5	0.9800	C13—H13	0.9300
C6—C7	1.497 (10)	C14—N1	1.502 (8)
C6—H6A	0.9700	C14—H14A	0.9700
C6—H6B	0.9700	C14—H14B	0.9700
C7—C8	1.527 (9)	N1—O4	1.214 (6)
C7—H7A	0.9700	N1—O3	1.223 (7)

C13—C1—C2	119.0 (6)	C7—C8—H8B	109.3
C13—C1—Br1	121.1 (5)	H8A—C8—H8B	108.0
C2—C1—Br1	119.8 (5)	O2—C9—C8	122.0 (5)
C3—C2—C1	119.6 (6)	O2—C9—C10	122.6 (5)
C3—C2—H2	120.2	C8—C9—C10	115.4 (5)
C1—C2—H2	120.2	C9—C10—C11	113.1 (4)
C2—C3—C4	120.3 (6)	C9—C10—C5	109.1 (4)
C2—C3—H3	119.8	C11—C10—C5	111.1 (4)
C4—C3—H3	119.8	C9—C10—H10	107.8
O1—C4—C3	116.4 (5)	C11—C10—H10	107.8
O1—C4—C12	122.0 (5)	C5—C10—H10	107.8
C3—C4—C12	121.5 (5)	C12—C11—C10	110.8 (4)
O1—C5—C6	106.3 (5)	C12—C11—C14	111.4 (4)
O1—C5—C10	108.8 (4)	C10—C11—C14	110.8 (4)
C6—C5—C10	111.9 (5)	C12—C11—H11	107.9
O1—C5—H5	109.9	C10—C11—H11	107.9
C6—C5—H5	109.9	C14—C11—H11	107.9
C10—C5—H5	109.9	C4—C12—C13	116.2 (5)
C7—C6—C5	111.7 (5)	C4—C12—C11	122.0 (5)
C7—C6—H6A	109.3	C13—C12—C11	121.5 (5)
C5—C6—H6A	109.3	C1—C13—C12	123.3 (6)
C7—C6—H6B	109.3	C1—C13—H13	118.3
C5—C6—H6B	109.3	C12—C13—H13	118.3
H6A—C6—H6B	107.9	N1—C14—C11	111.3 (5)
C6—C7—C8	111.8 (5)	N1—C14—H14A	109.4
C6—C7—H7A	109.2	C11—C14—H14A	109.4
C8—C7—H7A	109.2	N1—C14—H14B	109.4
C6—C7—H7B	109.2	C11—C14—H14B	109.4
C8—C7—H7B	109.2	H14A—C14—H14B	108.0
H7A—C7—H7B	107.9	O4—N1—O3	124.0 (6)
C9—C8—C7	111.5 (6)	O4—N1—C14	119.5 (5)
C9—C8—H8A	109.3	O3—N1—C14	116.4 (6)
C7—C8—H8A	109.3	C4—O1—C5	116.7 (4)
C9—C8—H8B	109.3

C13—C1—C2—C3	−1.3 (11)	C5—C10—C11—C14	−84.5 (5)
Br1—C1—C2—C3	−178.5 (6)	O1—C4—C12—C13	179.8 (5)
C1—C2—C3—C4	−0.6 (11)	C3—C4—C12—C13	−3.2 (9)
C2—C3—C4—O1	−179.9 (6)	O1—C4—C12—C11	−6.6 (8)
C2—C3—C4—C12	2.9 (11)	C3—C4—C12—C11	170.4 (6)
O1—C5—C6—C7	−61.4 (7)	C10—C11—C12—C4	−6.8 (7)
C10—C5—C6—C7	57.2 (7)	C14—C11—C12—C4	117.0 (5)
C5—C6—C7—C8	−55.4 (7)	C10—C11—C12—C13	166.4 (4)
C6—C7—C8—C9	51.6 (7)	C14—C11—C12—C13	−69.8 (6)
C7—C8—C9—O2	128.3 (7)	C2—C1—C13—C12	1.0 (10)
C7—C8—C9—C10	−51.1 (7)	Br1—C1—C13—C12	178.1 (4)
O2—C9—C10—C11	−3.6 (8)	C4—C12—C13—C1	1.2 (9)
C8—C9—C10—C11	175.8 (5)	C11—C12—C13—C1	−172.4 (6)
O2—C9—C10—C5	−127.8 (6)	C12—C11—C14—N1	162.8 (4)
C8—C9—C10—C5	51.6 (6)	C10—C11—C14—N1	−73.3 (5)
O1—C5—C10—C9	63.7 (5)	C11—C14—N1—O4	−25.2 (6)
C6—C5—C10—C9	−53.5 (6)	C11—C14—N1—O3	157.5 (4)
O1—C5—C10—C11	−61.7 (5)	C3—C4—O1—C5	166.4 (6)
C6—C5—C10—C11	−178.9 (5)	C12—C4—O1—C5	−16.5 (8)
C9—C10—C11—C12	−83.4 (6)	C6—C5—O1—C4	170.2 (5)
C5—C10—C11—C12	39.7 (6)	C10—C5—O1—C4	49.5 (7)
C9—C10—C11—C14	152.4 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1ⁱ	0.93	2.71	3.520 (9)	146
C8—H8B···O2ⁱⁱ	0.97	2.59	3.489 (6)	155
C8—H8A···O4ⁱⁱⁱ	0.97	2.54	3.253 (4)	131
C10—H10···O2^iv	0.98	2.53	3.300 (8)	135
C11—H11···O3^v	0.98	2.59	3.547 (8)	165

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₄BrNO₄
M_r	340.17
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	296
a, b, c (Å)	10.3457 (7), 5.4662 (5), 13.2446 (12)
β (°)	102.849 (2)
V (Å³)	730.25 (11)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.83
Crystal size (mm)	0.53 × 0.47 × 0.14

Data collection
Diffractometer	Rigaku R-AXIS RAPID
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.224, 0.673
No. of measured, independent and observed [I > 2σ(I)] reflections	6335, 2655, 1537
R_int	0.061
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.137, 1.00
No. of reflections	2655
No. of parameters	181
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.46
Absolute structure	Flack (1983), 1058 Friedel pairs
Absolute structure parameter	0.021 (17)

Computer programs: PROCESS-AUTO (Rigaku, 2006), CrystalStructure (Rigaku, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), WinGX (Farrugia, 2012).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1ⁱ	0.930	2.710	3.520 (9)	146
C8—H8B···O2ⁱⁱ	0.971	2.586	3.489 (6)	155
C8—H8A···O4ⁱⁱⁱ	0.970	2.535	3.253 (4)	131
C10—H10···O2^iv	0.981	2.533	3.300 (8)	135
C11—H11···O3^v	0.980	2.591	3.547 (8)	165

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

Acknowledgements

The authors thank Professor Jian-Ming Gu of Zhejiang University for his help.

References

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