3,9-Bis(2,4-dichloro-phen-yl)-2,4,8,10-tetra-oxaspiro-[5.5]undeca-ne.

In the title compound, C(19)H(16)Cl(4)O(4), the two halves of the mol-ecule are related by a crystallographic twofold rotation axis passing through the central spiro-C atom. The two non-planar six-membered heterocycles both adopt chair conformations, and the dihedral angle between the two benzene rings is 76.6 (1)°. In the crystal structure, inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into chains along the c axis.

Related literature

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

Experimental

Crystal data

C19H16Cl4O4

M = 450.12

Monoclinic,

a = 14.365 (2) Å

b = 5.7397 (9) Å

c = 11.7464 (19) Å

β = 93.275 (3)°

V = 966.9 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.64 mm−1

T = 295 K

0.21 × 0.21 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.878, T max = 0.905

5044 measured reflections

1686 independent reflections

1444 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.160

S = 1.02

1686 reflections

123 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.40 e Å−3

Data collection: SMART (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 (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810024712/ez2218sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810024712/ez2218Isup2.hkl

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

C19H16Cl4O4	F(000) = 460
Mr = 450.12	Dx = 1.546 Mg m−3
Monoclinic, P2/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.365 (2) Å	Cell parameters from 2876 reflections
b = 5.7397 (9) Å	θ = 2.8–29.5°
c = 11.7464 (19) Å	µ = 0.64 mm−1
β = 93.275 (3)°	T = 295 K
V = 966.9 (3) Å3	Block, colorless
Z = 2	0.21 × 0.21 × 0.16 mm

Bruker APEXII CCD diffractometer	1686 independent reflections
Radiation source: fine-focus sealed tube	1444 reflections with I > 2σ(I)
graphite	Rint = 0.022
φ and ω scans	θmax = 25.0°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −17→17
Tmin = 0.878, Tmax = 0.905	k = −6→6
5044 measured reflections	l = −13→8

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.160	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.133P)2] where P = (Fo2 + 2Fc2)/3
1686 reflections	(Δ/σ)max = 0.001
123 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.40 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	0.11833 (4)	1.10777 (11)	0.35541 (6)	0.0638 (3)
Cl2	0.09727 (5)	0.41534 (13)	0.65874 (6)	0.0751 (3)
O1	0.39049 (10)	1.0814 (2)	0.40196 (12)	0.0428 (4)
O2	0.37013 (9)	0.7923 (2)	0.26477 (12)	0.0414 (4)
C1	0.12123 (14)	0.7578 (4)	0.50648 (19)	0.0483 (6)
H1	0.0599	0.7995	0.5178	0.058*
C2	0.17289 (14)	0.8801 (3)	0.43034 (18)	0.0415 (5)
C3	0.26501 (12)	0.8219 (3)	0.41278 (16)	0.0361 (5)
C4	0.30282 (15)	0.6348 (4)	0.47363 (19)	0.0455 (5)
H4	0.3642	0.5922	0.4629	0.055*
C5	0.25309 (15)	0.5092 (4)	0.5495 (2)	0.0498 (6)
H5	0.2801	0.3841	0.5894	0.060*
C6	0.16219 (16)	0.5739 (4)	0.56487 (19)	0.0469 (6)
C7	0.32422 (14)	0.9531 (3)	0.33360 (17)	0.0388 (5)
H7	0.2855	1.0590	0.2857	0.047*
C8	0.44930 (15)	1.2158 (4)	0.3327 (2)	0.0492 (6)
H8A	0.4948	1.2992	0.3814	0.059*
H8B	0.4118	1.3298	0.2898	0.059*
C9	0.5000	1.0610 (4)	0.2500	0.0365 (6)
C10	0.42682 (15)	0.9102 (4)	0.18627 (17)	0.0427 (5)
H10A	0.3877	1.0073	0.1357	0.051*
H10B	0.4575	0.7965	0.1402	0.051*

	U11	U22	U33	U12	U13	U23
Cl1	0.0494 (4)	0.0675 (5)	0.0753 (6)	0.0257 (3)	0.0111 (3)	0.0162 (3)
Cl2	0.0745 (6)	0.0858 (6)	0.0674 (6)	−0.0222 (3)	0.0251 (4)	0.0137 (3)
O1	0.0476 (9)	0.0412 (8)	0.0411 (9)	−0.0055 (6)	0.0148 (7)	−0.0084 (5)
O2	0.0405 (8)	0.0478 (8)	0.0371 (8)	−0.0064 (6)	0.0124 (6)	−0.0095 (6)
C1	0.0344 (10)	0.0593 (13)	0.0524 (14)	0.0033 (9)	0.0125 (9)	−0.0040 (10)
C2	0.0357 (10)	0.0456 (12)	0.0435 (12)	0.0069 (8)	0.0048 (8)	−0.0030 (8)
C3	0.0316 (10)	0.0439 (10)	0.0331 (10)	0.0029 (8)	0.0033 (8)	−0.0044 (8)
C4	0.0355 (11)	0.0532 (13)	0.0480 (13)	0.0095 (8)	0.0043 (9)	0.0047 (9)
C5	0.0486 (12)	0.0515 (12)	0.0491 (13)	0.0040 (10)	0.0016 (10)	0.0098 (10)
C6	0.0476 (13)	0.0525 (12)	0.0414 (12)	−0.0086 (9)	0.0108 (9)	−0.0005 (9)
C7	0.0348 (10)	0.0474 (11)	0.0347 (11)	0.0071 (8)	0.0052 (8)	0.0018 (8)
C8	0.0559 (14)	0.0384 (11)	0.0554 (14)	−0.0039 (9)	0.0225 (11)	−0.0064 (9)
C9	0.0404 (15)	0.0340 (13)	0.0362 (15)	0.000	0.0114 (11)	0.000
C10	0.0417 (11)	0.0554 (12)	0.0315 (11)	−0.0013 (8)	0.0082 (9)	−0.0012 (8)

Cl1—C2	1.737 (2)	C4—H4	0.9300
Cl2—C6	1.741 (2)	C5—C6	1.379 (3)
O1—C7	1.417 (3)	C5—H5	0.9300
O1—C8	1.431 (2)	C7—H7	0.9800
O2—C7	1.414 (2)	C8—C9	1.531 (2)
O2—C10	1.434 (2)	C8—H8A	0.9700
C1—C6	1.373 (3)	C8—H8B	0.9700
C1—C2	1.386 (3)	C9—C10i	1.525 (2)
C1—H1	0.9300	C9—C10	1.525 (2)
C2—C3	1.391 (3)	C9—C8i	1.531 (2)
C3—C4	1.384 (3)	C10—H10A	0.9700
C3—C7	1.499 (3)	C10—H10B	0.9700
C4—C5	1.378 (3)
C7—O1—C8	110.95 (15)	O1—C7—C3	107.23 (15)
C7—O2—C10	111.11 (15)	O2—C7—H7	110.1
C6—C1—C2	118.81 (19)	O1—C7—H7	110.1
C6—C1—H1	120.6	C3—C7—H7	110.1
C2—C1—H1	120.6	O1—C8—C9	111.43 (16)
C1—C2—C3	121.53 (19)	O1—C8—H8A	109.3
C1—C2—Cl1	117.74 (15)	C9—C8—H8A	109.3
C3—C2—Cl1	120.73 (16)	O1—C8—H8B	109.3
C4—C3—C2	117.28 (19)	C9—C8—H8B	109.3
C4—C3—C7	119.37 (17)	H8A—C8—H8B	108.0
C2—C3—C7	123.34 (17)	C10i—C9—C10	110.8 (2)
C5—C4—C3	122.52 (19)	C10i—C9—C8i	107.54 (12)
C5—C4—H4	118.7	C10—C9—C8i	110.94 (12)
C3—C4—H4	118.7	C10i—C9—C8	110.94 (12)
C4—C5—C6	118.3 (2)	C10—C9—C8	107.54 (12)
C4—C5—H5	120.9	C8i—C9—C8	109.1 (2)
C6—C5—H5	120.9	O2—C10—C9	110.67 (14)
C1—C6—C5	121.6 (2)	O2—C10—H10A	109.5
C1—C6—Cl2	119.24 (17)	C9—C10—H10A	109.5
C5—C6—Cl2	119.17 (18)	O2—C10—H10B	109.5
O2—C7—O1	110.06 (16)	C9—C10—H10B	109.5
O2—C7—C3	109.08 (16)	H10A—C10—H10B	108.1
C6—C1—C2—C3	−0.6 (3)	C8—O1—C7—O2	62.5 (2)
C6—C1—C2—Cl1	178.60 (17)	C8—O1—C7—C3	−179.01 (15)
C1—C2—C3—C4	0.7 (3)	C4—C3—C7—O2	47.8 (2)
Cl1—C2—C3—C4	−178.44 (16)	C2—C3—C7—O2	−133.17 (19)
C1—C2—C3—C7	−178.38 (19)	C4—C3—C7—O1	−71.4 (2)
Cl1—C2—C3—C7	2.5 (3)	C2—C3—C7—O1	107.7 (2)
C2—C3—C4—C5	−0.4 (3)	C7—O1—C8—C9	−57.8 (2)
C7—C3—C4—C5	178.70 (19)	O1—C8—C9—C10i	−69.6 (2)
C3—C4—C5—C6	0.0 (4)	O1—C8—C9—C10	51.7 (2)
C2—C1—C6—C5	0.1 (3)	O1—C8—C9—C8i	172.1 (2)
C2—C1—C6—Cl2	−178.77 (16)	C7—O2—C10—C9	59.2 (2)
C4—C5—C6—C1	0.2 (3)	C10i—C9—C10—O2	69.36 (13)
C4—C5—C6—Cl2	179.05 (17)	C8i—C9—C10—O2	−171.24 (15)
C10—O2—C7—O1	−63.4 (2)	C8—C9—C10—O2	−52.1 (2)
C10—O2—C7—C3	179.21 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O2ii	0.93	2.58	3.425 (3)	152
C7—H7···Cl1	0.98	2.60	3.113 (2)	113

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O2i	0.93	2.58	3.425 (3)	152

Symmetry code: (i) .