5,5′-[(2,4-Dichloro­phen­yl)methyl­ene]bis­(2,2-dimethyl-1,3-dioxane-4,6-dione)

Zeng, W.-L.

doi:10.1107/S1600536811025384

organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o1894

doi:10.1107/S1600536811025384

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5,5′-[(2,4-Dichlorophenyl)methylene]bis(2,2-dimethyl-1,3-dioxane-4,6-dione)

Wu-Lan Zeng ^a ^*

^aMicroScale Science Institute, Department of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China
^*Correspondence e-mail: wulanzeng@163.com

(Received 22 June 2011; accepted 28 June 2011; online 2 July 2011)

The title compound, C₁₉H₁₈Cl₂O₈, was prepared by the reaction of 2,2-dimethyl-1,3-dioxane-4,6-dione and 2,4-dichlorobenzaldehyde in ethanol. The two 1,3-dioxane rings exhibit boat conformations. In the crystal, molecules are linked by weak intermolecular C—H⋯O and C—H⋯Cl hydrogen bonds, forming chains parallel to the a axis.

Related literature

For related structures, see: Zeng (2010 , 2011 ).

Experimental

Crystal data

C₁₉H₁₈Cl₂O₈
M_r = 445.23
Monoclinic, P 2₁ /c
a = 7.9522 (6) Å
b = 11.5145 (11) Å
c = 22.0939 (19) Å
β = 100.201 (1)°
V = 1991.1 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.37 mm⁻¹
T = 298 K
0.40 × 0.34 × 0.28 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.866, T_max = 0.903
9830 measured reflections
3519 independent reflections
1978 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.127
S = 1.03
3519 reflections
266 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O4ⁱ	0.98	2.32	3.220 (4)	151
C11—H11B⋯Cl1ⁱⁱ	0.96	2.75	3.387 (4)	125
C11—H11C⋯O4ⁱ	0.96	2.43	3.323 (4)	155
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811025384/rz2616sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811025384/rz2616Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811025384/rz2616Isup3.cml

checkCIF report

Comment top

In previous papers, the crystal structure of 5-(4-hydroxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione (Zeng, 2010) and 2,2-dimethyl-5-[(5-methylfuran-2-yl)methylidene]-1,3-dioxane-4,6-dione (Zeng, 2011) have been reported. As part of this ongoing search for new Meldrum's acid compounds, the title compound has been synthesized and its structure is reported here.

In the title compound (Fig. 1), bond lengths and angles fall in the usual ranges. The two 1,3-dioxane rings exhibit boat conformations. In the crystal structure, the molecules interact through weak intermolecular C—H···O and C—H···Cl hydrogen bonds (Table 1) to form chains parallel to the a axis.

Related literature top

For related structures, see: Zeng (2010, 2011).

Experimental top

A mixture of malonic acid (6.24 g, 0.06 mol) and acetic anhydride (9 ml) in concentrated sulfuric acid (0.25 ml) was stirred with water at 303 K, After dissolving, propan-2-one (3.48 g, 0.06 mol) was added dropwise into solution for 1 h. The reaction was allowed to proceed for 2 h. The mixture was cooled and filtered, and then an ethanol solution of 2,4-dichlorobenzaldehyde (10.44 g,0.06 mol) was added. The solution was then filtered and concentrated. Single crystals were obtained by evaporation of an petroleum ether/acetone (1:1 v/v) solution at room temperature over a period of several days.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (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, drawn with 30% probability ellipsoids and spheres of arbritrary size for the H atoms.

5,5'-[(2,4-Dichlorophenyl)methylene]bis(2,2-dimethyl-1,3-dioxane-4,6-dione) top

Crystal data top

C₁₉H₁₈Cl₂O₈	F(000) = 920
M_r = 445.23	D_x = 1.485 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2055 reflections
a = 7.9522 (6) Å	θ = 2.6–22.4°
b = 11.5145 (11) Å	µ = 0.37 mm⁻¹
c = 22.0939 (19) Å	T = 298 K
β = 100.201 (1)°	Block, colourless
V = 1991.1 (3) Å³	0.40 × 0.34 × 0.28 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3519 independent reflections
Radiation source: fine-focus sealed tube	1978 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
phi and ω scans	θ_max = 25.0°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→9
T_min = 0.866, T_max = 0.903	k = −13→13
9830 measured reflections	l = −26→16

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.127	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0473P)² + 0.9163P] where P = (F_o² + 2F_c²)/3
3519 reflections	(Δ/σ)_max < 0.001
266 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₉H₁₈Cl₂O₈	V = 1991.1 (3) Å³
M_r = 445.23	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.9522 (6) Å	µ = 0.37 mm⁻¹
b = 11.5145 (11) Å	T = 298 K
c = 22.0939 (19) Å	0.40 × 0.34 × 0.28 mm
β = 100.201 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3519 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1978 reflections with I > 2σ(I)
T_min = 0.866, T_max = 0.903	R_int = 0.039
9830 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.127	H-atom parameters constrained
S = 1.03	Δρ_max = 0.33 e Å⁻³
3519 reflections	Δρ_min = −0.28 e Å⁻³
266 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	0.34140 (13)	0.58466 (10)	0.82975 (4)	0.0791 (4)
Cl2	0.94290 (17)	0.39837 (13)	0.91959 (5)	0.1097 (5)
O1	0.4381 (3)	0.67539 (19)	0.54288 (9)	0.0534 (6)
O2	0.6398 (3)	0.77237 (18)	0.61607 (10)	0.0519 (6)
O3	0.2390 (3)	0.5720 (2)	0.57392 (10)	0.0633 (7)
O4	0.6173 (3)	0.75628 (19)	0.71323 (10)	0.0563 (7)
O5	−0.0131 (3)	0.43266 (19)	0.63977 (10)	0.0509 (6)
O6	0.1923 (3)	0.30698 (19)	0.61015 (10)	0.0530 (6)
O7	0.0621 (3)	0.5985 (2)	0.68504 (11)	0.0633 (7)
O8	0.4641 (3)	0.3549 (2)	0.62659 (11)	0.0576 (6)
C1	0.3785 (5)	0.6132 (3)	0.58613 (14)	0.0464 (8)
C2	0.5000 (4)	0.6011 (2)	0.64670 (13)	0.0393 (8)
H2	0.5877	0.5452	0.6399	0.047*
C3	0.5907 (4)	0.7152 (3)	0.66308 (15)	0.0422 (8)
C4	0.6071 (4)	0.7239 (3)	0.55467 (14)	0.0483 (9)
C5	0.6000 (5)	0.8257 (3)	0.51133 (15)	0.0637 (11)
H5A	0.5794	0.7982	0.4697	0.096*
H5B	0.7067	0.8667	0.5193	0.096*
H5C	0.5093	0.8770	0.5174	0.096*
C6	0.7397 (5)	0.6361 (3)	0.54565 (16)	0.0649 (10)
H6A	0.7325	0.5703	0.5718	0.097*
H6B	0.8512	0.6703	0.5559	0.097*
H6C	0.7204	0.6113	0.5035	0.097*
C7	0.1059 (4)	0.5050 (3)	0.67033 (14)	0.0453 (8)
C8	0.2861 (4)	0.4576 (3)	0.68544 (13)	0.0375 (7)
H8	0.2904	0.4136	0.7237	0.045*
C9	0.3256 (5)	0.3709 (3)	0.63918 (14)	0.0433 (8)
C10	0.0272 (4)	0.3142 (3)	0.62803 (15)	0.0486 (8)
C11	0.0244 (5)	0.2407 (3)	0.68364 (16)	0.0604 (10)
H11A	0.0455	0.1612	0.6742	0.091*
H11B	−0.0853	0.2469	0.6957	0.091*
H11C	0.1114	0.2669	0.7166	0.091*
C12	−0.1003 (5)	0.2776 (4)	0.57242 (16)	0.0731 (12)
H12A	−0.0942	0.3298	0.5390	0.110*
H12B	−0.2133	0.2795	0.5821	0.110*
H12C	−0.0746	0.2002	0.5608	0.110*
C13	0.4220 (4)	0.5546 (3)	0.70107 (13)	0.0385 (7)
H13	0.3633	0.6205	0.7162	0.046*
C14	0.5585 (4)	0.5159 (2)	0.75482 (13)	0.0360 (7)
C15	0.5303 (4)	0.5281 (3)	0.81477 (14)	0.0432 (8)
C16	0.6490 (5)	0.4927 (3)	0.86523 (14)	0.0524 (9)
H16	0.6284	0.5041	0.9049	0.063*
C17	0.7951 (5)	0.4412 (3)	0.85586 (16)	0.0552 (9)
C18	0.8268 (5)	0.4243 (3)	0.79810 (17)	0.0646 (11)
H18	0.9268	0.3878	0.7921	0.078*
C19	0.7089 (4)	0.4620 (3)	0.74818 (15)	0.0538 (9)
H19	0.7321	0.4505	0.7088	0.065*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0685 (7)	0.1167 (9)	0.0547 (6)	0.0359 (6)	0.0181 (5)	−0.0067 (6)
Cl2	0.0957 (9)	0.1545 (12)	0.0645 (7)	0.0415 (8)	−0.0254 (6)	0.0215 (7)
O1	0.0564 (15)	0.0646 (15)	0.0350 (13)	−0.0160 (12)	−0.0035 (10)	0.0125 (11)
O2	0.0649 (16)	0.0464 (13)	0.0429 (14)	−0.0127 (11)	0.0053 (11)	−0.0009 (11)
O3	0.0572 (17)	0.0817 (18)	0.0445 (14)	−0.0252 (14)	−0.0084 (11)	0.0136 (12)
O4	0.0752 (18)	0.0515 (14)	0.0378 (14)	−0.0083 (12)	−0.0014 (12)	−0.0084 (11)
O5	0.0375 (14)	0.0526 (14)	0.0589 (15)	−0.0018 (11)	−0.0017 (10)	0.0004 (11)
O6	0.0548 (16)	0.0554 (15)	0.0494 (14)	−0.0127 (12)	0.0112 (11)	−0.0114 (11)
O7	0.0477 (16)	0.0586 (17)	0.0805 (18)	0.0128 (12)	0.0029 (12)	−0.0087 (13)
O8	0.0479 (16)	0.0574 (15)	0.0708 (17)	−0.0008 (12)	0.0200 (13)	−0.0130 (12)
C1	0.051 (2)	0.048 (2)	0.0379 (19)	−0.0090 (17)	0.0009 (16)	0.0024 (15)
C2	0.0433 (19)	0.0407 (18)	0.0308 (17)	−0.0043 (15)	−0.0014 (13)	0.0011 (14)
C3	0.046 (2)	0.0401 (19)	0.038 (2)	−0.0034 (15)	−0.0009 (15)	0.0013 (16)
C4	0.052 (2)	0.053 (2)	0.0368 (19)	−0.0139 (18)	0.0017 (15)	0.0010 (16)
C5	0.076 (3)	0.064 (2)	0.052 (2)	−0.012 (2)	0.0134 (19)	0.0162 (19)
C6	0.070 (3)	0.070 (3)	0.056 (2)	0.005 (2)	0.0158 (19)	0.0018 (19)
C7	0.043 (2)	0.050 (2)	0.0423 (19)	0.0013 (17)	0.0040 (15)	0.0070 (17)
C8	0.0324 (18)	0.0442 (18)	0.0349 (17)	0.0001 (14)	0.0034 (13)	0.0028 (14)
C9	0.046 (2)	0.0400 (19)	0.044 (2)	−0.0019 (16)	0.0068 (16)	0.0028 (15)
C10	0.041 (2)	0.057 (2)	0.047 (2)	−0.0057 (17)	0.0045 (15)	0.0022 (17)
C11	0.057 (2)	0.060 (2)	0.062 (2)	−0.0143 (19)	0.0053 (18)	0.0097 (19)
C12	0.065 (3)	0.088 (3)	0.059 (3)	−0.022 (2)	−0.0093 (19)	−0.006 (2)
C13	0.0388 (19)	0.0397 (18)	0.0350 (17)	0.0031 (14)	0.0011 (13)	0.0013 (14)
C14	0.0363 (18)	0.0382 (17)	0.0325 (17)	−0.0001 (14)	0.0032 (13)	0.0029 (13)
C15	0.0409 (19)	0.050 (2)	0.0384 (19)	0.0044 (15)	0.0064 (14)	−0.0030 (15)
C16	0.061 (2)	0.064 (2)	0.0318 (19)	−0.0010 (19)	0.0061 (16)	−0.0034 (16)
C17	0.050 (2)	0.067 (2)	0.043 (2)	0.0078 (19)	−0.0061 (16)	0.0111 (18)
C18	0.048 (2)	0.091 (3)	0.054 (2)	0.025 (2)	0.0056 (18)	0.007 (2)
C19	0.047 (2)	0.075 (2)	0.0395 (19)	0.0140 (19)	0.0091 (16)	0.0045 (17)

Geometric parameters (Å, º) top

Cl1—C15	1.722 (3)	C6—H6C	0.9600
Cl2—C17	1.738 (3)	C7—C8	1.515 (4)
O1—C1	1.346 (4)	C8—C9	1.501 (4)
O1—C4	1.436 (4)	C8—C13	1.550 (4)
O2—C3	1.345 (4)	C8—H8	0.9800
O2—C4	1.447 (4)	C10—C11	1.495 (4)
O3—C1	1.193 (4)	C10—C12	1.508 (4)
O4—C3	1.189 (3)	C11—H11A	0.9600
O5—C7	1.349 (4)	C11—H11B	0.9600
O5—C10	1.435 (4)	C11—H11C	0.9600
O6—C9	1.355 (4)	C12—H12A	0.9600
O6—C10	1.439 (4)	C12—H12B	0.9600
O7—C7	1.194 (4)	C12—H12C	0.9600
O8—C9	1.197 (4)	C13—C14	1.527 (4)
C1—C2	1.512 (4)	C13—H13	0.9800
C2—C3	1.511 (4)	C14—C19	1.378 (4)
C2—C13	1.542 (4)	C14—C15	1.389 (4)
C2—H2	0.9800	C15—C16	1.389 (4)
C4—C6	1.500 (5)	C16—C17	1.352 (5)
C4—C5	1.508 (4)	C16—H16	0.9300
C5—H5A	0.9600	C17—C18	1.358 (5)
C5—H5B	0.9600	C18—C19	1.384 (4)
C5—H5C	0.9600	C18—H18	0.9300
C6—H6A	0.9600	C19—H19	0.9300
C6—H6B	0.9600

C1—O1—C4	120.9 (2)	O8—C9—C8	124.9 (3)
C3—O2—C4	120.4 (2)	O6—C9—C8	116.3 (3)
C7—O5—C10	121.2 (2)	O5—C10—O6	110.4 (2)
C9—O6—C10	120.9 (3)	O5—C10—C11	110.7 (3)
O3—C1—O1	118.8 (3)	O6—C10—C11	109.9 (3)
O3—C1—C2	125.9 (3)	O5—C10—C12	105.9 (3)
O1—C1—C2	115.3 (3)	O6—C10—C12	105.9 (3)
C3—C2—C1	109.6 (2)	C11—C10—C12	113.9 (3)
C3—C2—C13	110.9 (2)	C10—C11—H11A	109.5
C1—C2—C13	116.0 (3)	C10—C11—H11B	109.5
C3—C2—H2	106.6	H11A—C11—H11B	109.5
C1—C2—H2	106.6	C10—C11—H11C	109.5
C13—C2—H2	106.6	H11A—C11—H11C	109.5
O4—C3—O2	119.8 (3)	H11B—C11—H11C	109.5
O4—C3—C2	124.6 (3)	C10—C12—H12A	109.5
O2—C3—C2	115.6 (3)	C10—C12—H12B	109.5
O1—C4—O2	109.1 (3)	H12A—C12—H12B	109.5
O1—C4—C6	111.8 (3)	C10—C12—H12C	109.5
O2—C4—C6	111.8 (3)	H12A—C12—H12C	109.5
O1—C4—C5	105.0 (3)	H12B—C12—H12C	109.5
O2—C4—C5	106.0 (3)	C14—C13—C2	112.2 (2)
C6—C4—C5	112.8 (3)	C14—C13—C8	109.6 (2)
C4—C5—H5A	109.5	C2—C13—C8	115.9 (2)
C4—C5—H5B	109.5	C14—C13—H13	106.1
H5A—C5—H5B	109.5	C2—C13—H13	106.1
C4—C5—H5C	109.5	C8—C13—H13	106.1
H5A—C5—H5C	109.5	C19—C14—C15	115.9 (3)
H5B—C5—H5C	109.5	C19—C14—C13	124.0 (3)
C4—C6—H6A	109.5	C15—C14—C13	120.0 (3)
C4—C6—H6B	109.5	C16—C15—C14	122.3 (3)
H6A—C6—H6B	109.5	C16—C15—Cl1	116.7 (3)
C4—C6—H6C	109.5	C14—C15—Cl1	121.0 (2)
H6A—C6—H6C	109.5	C17—C16—C15	119.1 (3)
H6B—C6—H6C	109.5	C17—C16—H16	120.5
O7—C7—O5	118.7 (3)	C15—C16—H16	120.5
O7—C7—C8	125.1 (3)	C16—C17—C18	120.9 (3)
O5—C7—C8	116.1 (3)	C16—C17—Cl2	118.4 (3)
C9—C8—C7	113.2 (3)	C18—C17—Cl2	120.6 (3)
C9—C8—C13	114.1 (3)	C17—C18—C19	119.5 (3)
C7—C8—C13	112.6 (3)	C17—C18—H18	120.3
C9—C8—H8	105.3	C19—C18—H18	120.3
C7—C8—H8	105.3	C14—C19—C18	122.3 (3)
C13—C8—H8	105.3	C14—C19—H19	118.9
O8—C9—O6	118.8 (3)	C18—C19—H19	118.9

C4—O1—C1—O3	−178.1 (3)	C7—O5—C10—C11	80.4 (3)
C4—O1—C1—C2	1.0 (4)	C7—O5—C10—C12	−155.7 (3)
O3—C1—C2—C3	−140.5 (4)	C9—O6—C10—O5	41.7 (4)
O1—C1—C2—C3	40.4 (4)	C9—O6—C10—C11	−80.6 (3)
O3—C1—C2—C13	−14.1 (5)	C9—O6—C10—C12	155.9 (3)
O1—C1—C2—C13	166.9 (3)	C3—C2—C13—C14	−69.0 (3)
C4—O2—C3—O4	−179.5 (3)	C1—C2—C13—C14	165.2 (3)
C4—O2—C3—C2	−0.7 (4)	C3—C2—C13—C8	164.1 (2)
C1—C2—C3—O4	138.2 (3)	C1—C2—C13—C8	38.3 (4)
C13—C2—C3—O4	8.9 (4)	C9—C8—C13—C14	−89.5 (3)
C1—C2—C3—O2	−40.5 (4)	C7—C8—C13—C14	139.6 (3)
C13—C2—C3—O2	−169.9 (3)	C9—C8—C13—C2	38.8 (4)
C1—O1—C4—O2	−42.1 (4)	C7—C8—C13—C2	−92.1 (3)
C1—O1—C4—C6	82.0 (4)	C2—C13—C14—C19	−36.7 (4)
C1—O1—C4—C5	−155.4 (3)	C8—C13—C14—C19	93.6 (4)
C3—O2—C4—O1	41.9 (4)	C2—C13—C14—C15	147.1 (3)
C3—O2—C4—C6	−82.3 (4)	C8—C13—C14—C15	−82.6 (3)
C3—O2—C4—C5	154.5 (3)	C19—C14—C15—C16	2.5 (5)
C10—O5—C7—O7	−171.7 (3)	C13—C14—C15—C16	179.0 (3)
C10—O5—C7—C8	6.0 (4)	C19—C14—C15—Cl1	−175.5 (3)
O7—C7—C8—C9	−152.1 (3)	C13—C14—C15—Cl1	1.0 (4)
O5—C7—C8—C9	30.4 (4)	C14—C15—C16—C17	−2.0 (5)
O7—C7—C8—C13	−20.8 (4)	Cl1—C15—C16—C17	176.0 (3)
O5—C7—C8—C13	161.7 (2)	C15—C16—C17—C18	0.2 (6)
C10—O6—C9—O8	173.5 (3)	C15—C16—C17—Cl2	179.5 (3)
C10—O6—C9—C8	−6.4 (4)	C16—C17—C18—C19	1.0 (6)
C7—C8—C9—O8	150.0 (3)	Cl2—C17—C18—C19	−178.3 (3)
C13—C8—C9—O8	19.4 (4)	C15—C14—C19—C18	−1.3 (5)
C7—C8—C9—O6	−30.1 (4)	C13—C14—C19—C18	−177.6 (3)
C13—C8—C9—O6	−160.6 (2)	C17—C18—C19—C14	−0.4 (6)
C7—O5—C10—O6	−41.5 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O4ⁱ	0.98	2.32	3.220 (4)	151
C11—H11B···Cl1ⁱⁱ	0.96	2.75	3.387 (4)	125
C11—H11C···O4ⁱ	0.96	2.43	3.323 (4)	155

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

Experimental details

Crystal data
Chemical formula	C₁₉H₁₈Cl₂O₈
M_r	445.23
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	7.9522 (6), 11.5145 (11), 22.0939 (19)
β (°)	100.201 (1)
V (Å³)	1991.1 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.37
Crystal size (mm)	0.40 × 0.34 × 0.28

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.866, 0.903
No. of measured, independent and observed [I > 2σ(I)] reflections	9830, 3519, 1978
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.127, 1.03
No. of reflections	3519
No. of parameters	266
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.28

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O4ⁱ	0.98	2.32	3.220 (4)	151
C11—H11B···Cl1ⁱⁱ	0.96	2.75	3.387 (4)	125
C11—H11C···O4ⁱ	0.96	2.43	3.323 (4)	155

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

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zeng, W.-L. (2010). Acta Cryst. E66, o2319. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zeng, W.-L. (2011). Acta Cryst. E67, o478. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 67| Part 8| August 2011| Page o1894

doi:10.1107/S1600536811025384

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

5,5′-[(2,4-Di­chloro­phen­yl)methyl­ene]bis­­(2,2-di­methyl-1,3-dioxane-4,6-dione)

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Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

5,5′-[(2,4-Dichlorophenyl)methylene]bis(2,2-dimethyl-1,3-dioxane-4,6-dione)