rac-3,9-Bis(3-chloro­phen­yl)-2,4,8,10-tetra­oxaspiro­[5.5]undeca­ne

Li, Z.; Zhou, B.; Chen, L.; Ge, L.; Sun, X.

doi:10.1107/S1600536811037172

organic compounds

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ISSN: 2056-9890

Volume 67| Part 10| October 2011| Page o2672

https://doi.org/10.1107/S1600536811037172

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rac-3,9-Bis(3-chlorophenyl)-2,4,8,10-tetraoxaspiro[5.5]undecane

Zhengyi Li,^a Beibei Zhou,^a Liang Chen,^a Ling Ge ^a and Xiaoqiang Sun ^a ^*

^aKey Laboratory of Fine Chemical Engineering, Changzhou University, Changzhou 213164, Jiangsu, People's Republic of China
^*Correspondence e-mail: chemsxq@yahoo.com.cn

(Received 23 July 2011; accepted 13 September 2011; online 17 September 2011)

In the title compound, C₁₉H₁₈Cl₂O₄, the two non-planar six-membered heterocycles passing through the spiro-C atom both adopt chair conformations, and the dihedral angle between the two benzene rings is 7.2 (1)°. In the crystal, the enantiomers with R and S configurations are generated by the symmetry elements of the centrosymmetric space group, forming a racemic crystal. Intermolecular C—H⋯π and weak C—H⋯O interactions link the molecules in the crystal structure.

Related literature

For general background to spiranes, see: Cismaş et al. (2005 ); Mihiş et al. (2008 ); Sun et al. (2010 ).

Experimental

Crystal data

C₁₉H₁₈Cl₂O₄
M_r = 381.23
Monoclinic, P 2₁ /c
a = 13.0924 (13) Å
b = 5.8473 (6) Å
c = 23.061 (2) Å
β = 92.865 (2)°
V = 1763.2 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.39 mm⁻¹
T = 296 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.892, T_max = 0.926
9216 measured reflections
3083 independent reflections
2669 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.091
S = 1.01
3083 reflections
227 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12B⋯Cg1ⁱ	0.97	2.70	3.632 (2)	162
C9—H9A⋯O3ⁱⁱ	0.97	2.64	3.402 (2)	135
C11—H11B⋯O3ⁱⁱⁱ	0.97	2.61	3.530 (2)	158
Symmetry codes: (i) -x+2, -y, -z+1; (ii) $[-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); 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 I, global. DOI: https://doi.org/10.1107/S1600536811037172/kp2345sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811037172/kp2345Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811037172/kp2345Isup3.cml

checkCIF report

Comment top

Owing to the characteristic axial and helical chirality, the stereochemistry of spiranes with six-membered rings has been extensively studied (Cismaş et al., 2005). In the past three decades, most of these investigations were carried out with spiranes containing 1,3-dioxane units (Mihiş et al., 2008; Sun et al., 2010). We herein present the structure of 3,9-bis(3-chlorophenyl)-2,4,8,10-tetraoxaspiro[5.5]undecane (Fig. 1).

In the title compound, the two nonplanar six-membered heterocycles [(O1, O2 and C7–C10) and (O3, O4 and C10–C13)] passing through the spiro-C atom (C10) both adopt chair conformations, and the dihedral angle between the two benzene rings (C1–C6 and C14–C19) is 7.2 (1)°. In the crystal packing structure (Fig. 2), the enantiomers with R and S configurations are generated by the symmetry elements of the centrosymmetric groups forming a racemate. Intermolecular weak C–H···O interactions link molecules with the same configuration (R or S) into the two chains chains along the b axis. The chains are further connected by C–H···π interactions [C12–H12B···Cg1ⁱ = 2.70 Å; (i) -x + 2, -y, -z + 1; Cg1 is the centroid of benzene ring (C1–C6); Table 1] creating a racemic network.

Related literature top

For general background to spiranes, see: Cismaş et al. (2005); Mihiş et al. (2008); Sun et al. (2010).

Experimental top

To a solution of 3-chlorobenzaldehyde (7.32 mmol, 1.03 g) and pentaerythritol (4 mmol, 0.54 g) in toluene (30 mL), phosphotungstic acid (30 mg) as catalyst was added, respectively. The mixtures were refluxed for 4 h to complete the reaction. After reaction, the mixture was evaporated under vacuum and the residuces were washed with 5% sodium bicarboinate (20 mL) and 50% ethanol (20 mL), respectively. The pure product recrystallised from ethanol to afford colourless crystals (yield 65%, m.p. 397–398 K). Single crystals suitable for X-ray diffraction were also obtained by evaporation of an enthanol solution.

Structure description top

For general background to spiranes, see: Cismaş et al. (2005); Mihiş et al. (2008); Sun et al. (2010).

Computing details top

Data collection: APEX2 (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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 molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Crystal packing of (I). Hydrogen bonds are shown as dashed lines.

rac-3,9-Bis(3-chlorophenyl)-2,4,8,10-tetraoxaspiro[5.5]undecane top

Crystal data top

C₁₉H₁₈Cl₂O₄	F(000) = 792
M_r = 381.23	D_x = 1.436 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 397 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 13.0924 (13) Å	Cell parameters from 5568 reflections
b = 5.8473 (6) Å	θ = 2.4–30.2°
c = 23.061 (2) Å	µ = 0.39 mm⁻¹
β = 92.865 (2)°	T = 296 K
V = 1763.2 (3) Å³	PRISM, colourless
Z = 4	0.30 × 0.20 × 0.20 mm

Data collection top

Bruker APEXII CCD diffractometer	3083 independent reflections
Radiation source: fine-focus sealed tube	2669 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
φ and ω scans	θ_max = 25.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −15→15
T_min = 0.892, T_max = 0.926	k = −6→6
9216 measured reflections	l = −27→23

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)] = 0.034	H-atom parameters constrained
wR(F²) = 0.091	w = 1/[σ²(F_o²) + (0.045P)² + 0.585P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.001
3083 reflections	Δρ_max = 0.23 e Å⁻³
227 parameters	Δρ_min = −0.37 e Å⁻³
0 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: 0.0101 (15)

Crystal data top

C₁₉H₁₈Cl₂O₄	V = 1763.2 (3) Å³
M_r = 381.23	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.0924 (13) Å	µ = 0.39 mm⁻¹
b = 5.8473 (6) Å	T = 296 K
c = 23.061 (2) Å	0.30 × 0.20 × 0.20 mm
β = 92.865 (2)°

Data collection top

Bruker APEXII CCD diffractometer	3083 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2669 reflections with I > 2σ(I)
T_min = 0.892, T_max = 0.926	R_int = 0.044
9216 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.091	H-atom parameters constrained
S = 1.01	Δρ_max = 0.23 e Å⁻³
3083 reflections	Δρ_min = −0.37 e Å⁻³
227 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	1.44666 (4)	−0.09142 (9)	0.42374 (2)	0.06281 (18)
Cl2	0.60790 (4)	0.03575 (11)	0.87193 (2)	0.0707 (2)
C10	1.00108 (11)	−0.0663 (3)	0.63687 (6)	0.0355 (3)
C7	1.18050 (11)	0.0270 (3)	0.57866 (6)	0.0381 (4)
H7	1.2282	−0.0646	0.6032	0.046*
C13	0.81522 (11)	0.0410 (3)	0.68608 (6)	0.0367 (3)
H13	0.7765	−0.0790	0.6650	0.044*
C14	0.74431 (11)	0.1662 (3)	0.72470 (6)	0.0365 (3)
C6	1.23665 (11)	0.1316 (3)	0.52994 (6)	0.0360 (3)
C9	1.08461 (12)	0.0975 (3)	0.65948 (7)	0.0437 (4)
H9A	1.0544	0.2177	0.6820	0.052*
H9B	1.1333	0.0154	0.6848	0.052*
C12	0.91461 (12)	0.0658 (3)	0.60524 (6)	0.0426 (4)
H12A	0.9431	0.1715	0.5779	0.051*
H12B	0.8704	−0.0401	0.5835	0.051*
C19	0.71569 (12)	0.0629 (3)	0.77554 (7)	0.0407 (4)
H19	0.7439	−0.0767	0.7871	0.049*
C18	0.64487 (12)	0.1693 (3)	0.80883 (7)	0.0452 (4)
C1	1.31014 (11)	−0.0007 (3)	0.50473 (7)	0.0383 (3)
H1	1.3269	−0.1442	0.5198	0.046*
C11	0.95635 (13)	−0.2022 (3)	0.68599 (7)	0.0466 (4)
H11A	0.9156	−0.3274	0.6697	0.056*
H11B	1.0116	−0.2670	0.7103	0.056*
C15	0.70256 (13)	0.3758 (3)	0.70861 (8)	0.0475 (4)
H15	0.7217	0.4465	0.6747	0.057*
C2	1.35834 (12)	0.0819 (3)	0.45714 (7)	0.0413 (4)
C8	1.04953 (14)	−0.2341 (3)	0.59572 (8)	0.0479 (4)
H8A	1.0958	−0.3346	0.6178	0.057*
H8B	0.9965	−0.3276	0.5768	0.057*
C3	1.33736 (13)	0.2967 (3)	0.43493 (7)	0.0471 (4)
H3	1.3716	0.3520	0.4035	0.057*
C5	1.21370 (13)	0.3469 (3)	0.50771 (7)	0.0451 (4)
H5	1.1645	0.4368	0.5244	0.054*
C17	0.60229 (13)	0.3780 (3)	0.79319 (8)	0.0533 (5)
H17	0.5546	0.4477	0.8160	0.064*
C4	1.26424 (14)	0.4277 (3)	0.46054 (8)	0.0505 (4)
H4	1.2487	0.5724	0.4459	0.061*
C16	0.63242 (14)	0.4803 (3)	0.74285 (9)	0.0567 (5)
H16	0.6052	0.6216	0.7318	0.068*
O3	0.89369 (8)	−0.06191 (19)	0.72093 (4)	0.0415 (3)
O1	1.10447 (8)	−0.11743 (19)	0.55266 (5)	0.0421 (3)
O4	0.85569 (8)	0.1908 (2)	0.64567 (4)	0.0429 (3)
O2	1.13674 (8)	0.19688 (19)	0.61245 (5)	0.0441 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0534 (3)	0.0747 (4)	0.0629 (3)	0.0064 (2)	0.0281 (2)	−0.0002 (2)
Cl2	0.0728 (3)	0.0869 (4)	0.0552 (3)	−0.0017 (3)	0.0312 (2)	0.0047 (3)
C10	0.0400 (8)	0.0339 (8)	0.0332 (7)	0.0029 (6)	0.0077 (6)	−0.0012 (6)
C7	0.0375 (8)	0.0435 (9)	0.0333 (8)	0.0046 (7)	0.0032 (6)	−0.0027 (6)
C13	0.0374 (8)	0.0396 (8)	0.0333 (8)	−0.0012 (6)	0.0030 (6)	−0.0001 (6)
C14	0.0320 (7)	0.0410 (8)	0.0365 (8)	−0.0008 (6)	0.0015 (6)	−0.0031 (6)
C6	0.0364 (8)	0.0403 (8)	0.0314 (7)	−0.0037 (6)	0.0015 (6)	−0.0043 (6)
C9	0.0440 (8)	0.0575 (10)	0.0301 (8)	−0.0008 (8)	0.0061 (6)	−0.0084 (7)
C12	0.0412 (8)	0.0578 (10)	0.0293 (7)	0.0037 (7)	0.0056 (6)	0.0027 (7)
C19	0.0395 (8)	0.0414 (9)	0.0415 (8)	−0.0005 (7)	0.0050 (7)	−0.0017 (7)
C18	0.0392 (8)	0.0554 (10)	0.0417 (9)	−0.0061 (8)	0.0099 (7)	−0.0063 (7)
C1	0.0373 (8)	0.0393 (8)	0.0384 (8)	−0.0006 (7)	0.0029 (6)	0.0014 (6)
C11	0.0546 (10)	0.0402 (9)	0.0467 (9)	0.0128 (8)	0.0180 (7)	0.0077 (7)
C15	0.0473 (9)	0.0479 (10)	0.0478 (9)	0.0060 (8)	0.0067 (7)	0.0053 (8)
C2	0.0353 (8)	0.0496 (9)	0.0394 (8)	−0.0052 (7)	0.0057 (6)	−0.0027 (7)
C8	0.0592 (10)	0.0354 (9)	0.0511 (9)	−0.0028 (8)	0.0229 (8)	−0.0051 (7)
C3	0.0516 (9)	0.0505 (10)	0.0395 (8)	−0.0119 (8)	0.0049 (7)	0.0046 (7)
C5	0.0533 (9)	0.0393 (9)	0.0426 (9)	0.0041 (7)	0.0032 (7)	−0.0061 (7)
C17	0.0423 (9)	0.0600 (11)	0.0587 (11)	0.0058 (8)	0.0130 (8)	−0.0143 (9)
C4	0.0662 (11)	0.0379 (9)	0.0471 (9)	−0.0035 (8)	0.0004 (8)	0.0042 (7)
C16	0.0528 (10)	0.0491 (10)	0.0686 (12)	0.0148 (9)	0.0065 (9)	−0.0016 (9)
O3	0.0461 (6)	0.0455 (6)	0.0338 (5)	0.0124 (5)	0.0106 (5)	0.0071 (5)
O1	0.0510 (6)	0.0384 (6)	0.0382 (6)	−0.0059 (5)	0.0149 (5)	−0.0094 (5)
O4	0.0453 (6)	0.0475 (6)	0.0369 (6)	0.0117 (5)	0.0112 (5)	0.0103 (5)
O2	0.0475 (6)	0.0464 (6)	0.0395 (6)	−0.0082 (5)	0.0139 (5)	−0.0138 (5)

Geometric parameters (Å, º) top

Cl1—C2	1.7456 (16)	C12—H12B	0.9700
Cl2—C18	1.7413 (17)	C19—C18	1.381 (2)
C10—C11	1.524 (2)	C19—H19	0.9300
C10—C8	1.525 (2)	C18—C17	1.382 (3)
C10—C9	1.526 (2)	C1—C2	1.380 (2)
C10—C12	1.526 (2)	C1—H1	0.9300
C7—O2	1.4026 (18)	C11—O3	1.4356 (18)
C7—O1	1.4153 (19)	C11—H11A	0.9700
C7—C6	1.503 (2)	C11—H11B	0.9700
C7—H7	0.9800	C15—C16	1.383 (2)
C13—O4	1.4019 (18)	C15—H15	0.9300
C13—O3	1.4074 (18)	C2—C3	1.379 (2)
C13—C14	1.508 (2)	C8—O1	1.4285 (19)
C13—H13	0.9800	C8—H8A	0.9700
C14—C15	1.385 (2)	C8—H8B	0.9700
C14—C19	1.387 (2)	C3—C4	1.382 (2)
C6—C1	1.385 (2)	C3—H3	0.9300
C6—C5	1.387 (2)	C5—C4	1.384 (2)
C9—O2	1.4332 (19)	C5—H5	0.9300
C9—H9A	0.9700	C17—C16	1.381 (3)
C9—H9B	0.9700	C17—H17	0.9300
C12—O4	1.4388 (18)	C4—H4	0.9300
C12—H12A	0.9700	C16—H16	0.9300

C11—C10—C8	108.33 (13)	C17—C18—Cl2	119.26 (13)
C11—C10—C9	111.63 (14)	C2—C1—C6	119.55 (15)
C8—C10—C9	107.65 (13)	C2—C1—H1	120.2
C11—C10—C12	108.41 (13)	C6—C1—H1	120.2
C8—C10—C12	110.49 (13)	O3—C11—C10	111.77 (12)
C9—C10—C12	110.32 (14)	O3—C11—H11A	109.3
O2—C7—O1	111.08 (12)	C10—C11—H11A	109.3
O2—C7—C6	110.82 (13)	O3—C11—H11B	109.3
O1—C7—C6	106.63 (12)	C10—C11—H11B	109.3
O2—C7—H7	109.4	H11A—C11—H11B	107.9
O1—C7—H7	109.4	C16—C15—C14	120.17 (16)
C6—C7—H7	109.4	C16—C15—H15	119.9
O4—C13—O3	110.93 (12)	C14—C15—H15	119.9
O4—C13—C14	110.70 (12)	C3—C2—C1	121.58 (15)
O3—C13—C14	108.89 (12)	C3—C2—Cl1	119.28 (12)
O4—C13—H13	108.8	C1—C2—Cl1	119.14 (13)
O3—C13—H13	108.8	O1—C8—C10	111.40 (13)
C14—C13—H13	108.8	O1—C8—H8A	109.3
C15—C14—C19	119.48 (15)	C10—C8—H8A	109.3
C15—C14—C13	121.20 (14)	O1—C8—H8B	109.3
C19—C14—C13	119.21 (14)	C10—C8—H8B	109.3
C1—C6—C5	119.62 (14)	H8A—C8—H8B	108.0
C1—C6—C7	117.54 (14)	C2—C3—C4	118.41 (15)
C5—C6—C7	122.74 (14)	C2—C3—H3	120.8
O2—C9—C10	110.88 (12)	C4—C3—H3	120.8
O2—C9—H9A	109.5	C4—C5—C6	119.81 (16)
C10—C9—H9A	109.5	C4—C5—H5	120.1
O2—C9—H9B	109.5	C6—C5—H5	120.1
C10—C9—H9B	109.5	C16—C17—C18	118.26 (16)
H9A—C9—H9B	108.1	C16—C17—H17	120.9
O4—C12—C10	110.87 (12)	C18—C17—H17	120.9
O4—C12—H12A	109.5	C3—C4—C5	121.02 (16)
C10—C12—H12A	109.5	C3—C4—H4	119.5
O4—C12—H12B	109.5	C5—C4—H4	119.5
C10—C12—H12B	109.5	C17—C16—C15	120.94 (17)
H12A—C12—H12B	108.1	C17—C16—H16	119.5
C18—C19—C14	119.40 (15)	C15—C16—H16	119.5
C18—C19—H19	120.3	C13—O3—C11	110.19 (12)
C14—C19—H19	120.3	C7—O1—C8	111.00 (12)
C19—C18—C17	121.73 (16)	C13—O4—C12	110.26 (12)
C19—C18—Cl2	119.00 (14)	C7—O2—C9	110.87 (12)

O4—C13—C14—C15	19.0 (2)	C6—C1—C2—Cl1	−177.16 (11)
O3—C13—C14—C15	141.19 (15)	C11—C10—C8—O1	−172.53 (14)
O4—C13—C14—C19	−164.95 (13)	C9—C10—C8—O1	−51.68 (18)
O3—C13—C14—C19	−42.74 (18)	C12—C10—C8—O1	68.85 (18)
O2—C7—C6—C1	159.48 (13)	C1—C2—C3—C4	−1.7 (2)
O1—C7—C6—C1	−79.51 (16)	Cl1—C2—C3—C4	177.45 (13)
O2—C7—C6—C5	−24.2 (2)	C1—C6—C5—C4	0.1 (2)
O1—C7—C6—C5	96.80 (17)	C7—C6—C5—C4	−176.16 (15)
C11—C10—C9—O2	170.89 (12)	C19—C18—C17—C16	−0.1 (3)
C8—C10—C9—O2	52.13 (17)	Cl2—C18—C17—C16	−179.73 (15)
C12—C10—C9—O2	−68.50 (16)	C2—C3—C4—C5	0.6 (3)
C11—C10—C12—O4	50.16 (18)	C6—C5—C4—C3	0.2 (3)
C8—C10—C12—O4	168.73 (13)	C18—C17—C16—C15	0.7 (3)
C9—C10—C12—O4	−72.36 (16)	C14—C15—C16—C17	−0.4 (3)
C15—C14—C19—C18	0.9 (2)	O4—C13—O3—C11	−63.94 (16)
C13—C14—C19—C18	−175.20 (14)	C14—C13—O3—C11	173.99 (12)
C14—C19—C18—C17	−0.7 (2)	C10—C11—O3—C13	56.69 (18)
C14—C19—C18—Cl2	178.92 (12)	O2—C7—O1—C8	−61.88 (16)
C5—C6—C1—C2	−1.1 (2)	C6—C7—O1—C8	177.28 (12)
C7—C6—C1—C2	175.31 (14)	C10—C8—O1—C7	57.07 (18)
C8—C10—C11—O3	−169.67 (13)	O3—C13—O4—C12	64.98 (15)
C9—C10—C11—O3	71.97 (18)	C14—C13—O4—C12	−174.01 (11)
C12—C10—C11—O3	−49.75 (18)	C10—C12—O4—C13	−58.23 (16)
C19—C14—C15—C16	−0.4 (3)	O1—C7—O2—C9	62.62 (16)
C13—C14—C15—C16	175.67 (16)	C6—C7—O2—C9	−179.05 (12)
C6—C1—C2—C3	2.0 (2)	C10—C9—O2—C7	−58.53 (16)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12B···Cg1ⁱ	0.97	2.70	3.632 (2)	162
C9—H9A···O3ⁱⁱ	0.97	2.64	3.402 (2)	135
C11—H11B···O3ⁱⁱⁱ	0.97	2.61	3.530 (2)	158

Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+2, y+1/2, −z+3/2; (iii) −x+2, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₈Cl₂O₄
M_r	381.23
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	13.0924 (13), 5.8473 (6), 23.061 (2)
β (°)	92.865 (2)
V (Å³)	1763.2 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.39
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.892, 0.926
No. of measured, independent and observed [I > 2σ(I)] reflections	9216, 3083, 2669
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.091, 1.01
No. of reflections	3083
No. of parameters	227
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.37

Computer programs: APEX2 (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12B···Cg1ⁱ	0.97	2.70	3.632 (2)	162.0
C9—H9A···O3ⁱⁱ	0.97	2.64	3.402 (2)	135.4
C11—H11B···O3ⁱⁱⁱ	0.97	2.61	3.530 (2)	157.7

Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+2, y+1/2, −z+3/2; (iii) −x+2, y−1/2, −z+3/2.

Acknowledgements

We gratefully acknowledge financial support from the Natural Science Foundation of China (Nos. 20872051 and 21002009) and the Priority Academic Program Development of Jiangsu Higher Education Institutions.

References

Bruker (2000). SAINT, APEX2 and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cismaş, C., Terec, A., Mager, S. & Grosu, I. (2005). Curr. Org. Chem. 9, 1287–1314. Google Scholar
Mihiş, A., Condamine, E., Bogdan, E., Terec, A., Kurtán, T. & Grosu, I. (2008). Molecules, 13, 2848–2858. Web of Science PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sun, X., Yu, S.-L., Li, Z.-Y. & Yang, Y. (2010). J. Mol. Struct. 973, 152–156. Web of Science CSD CrossRef CAS Google Scholar

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