5,5'-[(2,4-Dichloro-phen-yl)methyl-ene]bis-(2,2-dimethyl-1,3-dioxane-4,6-dione).

The title compound, C(19)H(18)Cl(2)O(8), was prepared by the reaction of 2,2-dimethyl-1,3-dioxane-4,6-dione and 2,4-dichloro-benzaldehyde in ethanol. The two 1,3-dioxane rings exhibit boat conformations. In the crystal, mol-ecules are linked by weak inter-molecular 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 = 445.23

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.127

S = 1.03

3519 reflections

266 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.28 e Å−3

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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811025384/rz2616sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811025384/rz2616Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C19H18Cl2O8	F(000) = 920
Mr = 445.23	Dx = 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

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

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(Fo2) + (0.0473P)2 + 0.9163P] where P = (Fo2 + 2Fc2)/3
3519 reflections	(Δ/σ)max < 0.001
266 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) .