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

The complete mol­ecule of the title compound, C₁₉H₁₈Cl₂O₄, is generated by a crystallographic twofold axis that passes through the spiro C atom. The 1,3-dioxane ring adopts a chair conformation and the phenyl substituent occupies an equatorial site.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.032
• wR factor = 0.092
• Data-to-parameter ratio = 16.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          1
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         11
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600          2

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Related literature

For the crystal structure of 3,9-diphenyl-2,4,8,10-tetraoxaspiro[5.5]undecane, see: Wang et al. (2006).

S1. Experimental

Pentaerythritol (2 g, 0.014 mol), 2-chlorobenzaldehyde(4.6 g, 0.033 mol), toluene (12 ml) and a catalytic amount (0.2 g) of p-toluenesulfonic acid were heated for 4 hours. The mixture was cooled and then filtered. The organic phase was washed with water and 5% sodium bicarbonate (20 ml). The solvent was evaporated and the product recrystallized from ethyl acetate to afford colourless crystals (yield 70%); m.p. 418.5–419 K.

S2. Refinement

H-atoms were placed in calculated positions (C—H 0.95–0.99 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2U(C).

Structure description

For the crystal structure of 3,9-diphenyl-2,4,8,10-tetraoxaspiro[5.5]undecane, see: Wang et al. (2006).

Computing details

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures

Fig. 1. Anisotropic displacement ellipsoid plot of C19H18Cl2O4 at the 70% probability level; hydrogen atoms are shown as spheres of arbitrary radius.

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

Crystal data

C19H18Cl2O4	F(000) = 792
Mr = 381.23	Dx = 1.472 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5105 reflections
a = 10.7116 (5) Å	θ = 2.4–27.1°
b = 9.4693 (5) Å	µ = 0.40 mm^−1
c = 17.7080 (9) Å	T = 173 K
β = 106.745 (1)°	Block, yellow
V = 1719.98 (15) Å^3	0.46 × 0.42 × 0.22 mm
Z = 4

Data collection

Bruker SMART APEX diffractometer	1883 independent reflections
Radiation source: fine-focus sealed tube	1707 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.015
ω scans	θmax = 27.1°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.838, Tmax = 0.917	k = −12→11
6932 measured reflections	l = −22→22

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.092	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0542P)^2 + 1.3419P] where P = (Fo^2 + 2Fc^2)/3
1883 reflections	(Δ/σ)max = 0.001
114 parameters	Δρmax = 0.30 e Å^−3
0 restraints	Δρmin = −0.25 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	−0.05287 (3)	0.53900 (4)	0.14620 (2)	0.04156 (14)
O1	0.30941 (9)	0.51739 (10)	0.13408 (5)	0.0283 (2)
O2	0.31431 (8)	0.34130 (10)	0.22630 (5)	0.0298 (2)
C1	−0.00068 (12)	0.40843 (14)	0.09327 (7)	0.0261 (3)
C2	−0.09394 (12)	0.34711 (16)	0.03040 (8)	0.0329 (3)
H2	−0.1815	0.3799	0.0160	0.040*
C3	−0.05826 (13)	0.23835 (18)	−0.01081 (8)	0.0381 (3)
H3	−0.1214	0.1960	−0.0539	0.046*
C4	0.07000 (15)	0.19038 (18)	0.01047 (9)	0.0398 (3)
H4	0.0941	0.1134	−0.0168	0.048*
C5	0.16221 (13)	0.25578 (16)	0.07170 (8)	0.0342 (3)
H5	0.2501	0.2242	0.0852	0.041*
C6	0.12931 (12)	0.36636 (14)	0.11379 (7)	0.0259 (3)
C7	0.23515 (12)	0.44177 (14)	0.17524 (8)	0.0265 (3)
H7	0.1960	0.5084	0.2059	0.032*
C8	0.40974 (12)	0.59806 (14)	0.18815 (8)	0.0303 (3)
H8A	0.3692	0.6690	0.2148	0.036*
H8B	0.4614	0.6491	0.1586	0.036*
C9	0.5000	0.50311 (19)	0.2500	0.0240 (3)
C10	0.41483 (12)	0.41154 (15)	0.28641 (7)	0.0291 (3)
H10A	0.4699	0.3402	0.3216	0.035*
H10B	0.3743	0.4715	0.3187	0.035*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0294 (2)	0.0446 (2)	0.0492 (2)	0.01101 (14)	0.00891 (16)	−0.00178 (15)
O1	0.0231 (4)	0.0307 (5)	0.0247 (4)	−0.0053 (4)	−0.0034 (4)	0.0058 (4)
O2	0.0220 (4)	0.0323 (5)	0.0290 (5)	−0.0030 (4)	−0.0024 (4)	0.0091 (4)
C1	0.0204 (6)	0.0298 (6)	0.0271 (6)	0.0012 (5)	0.0051 (5)	0.0078 (5)
C2	0.0182 (6)	0.0495 (8)	0.0282 (6)	−0.0041 (5)	0.0022 (5)	0.0102 (6)
C3	0.0283 (7)	0.0560 (9)	0.0275 (6)	−0.0157 (6)	0.0042 (5)	−0.0035 (6)
C4	0.0353 (7)	0.0459 (9)	0.0389 (8)	−0.0068 (6)	0.0120 (6)	−0.0098 (6)
C5	0.0223 (6)	0.0391 (7)	0.0390 (7)	0.0011 (5)	0.0055 (5)	−0.0028 (6)
C6	0.0194 (6)	0.0293 (6)	0.0262 (6)	−0.0012 (5)	0.0024 (5)	0.0052 (5)
C7	0.0191 (6)	0.0295 (6)	0.0278 (6)	0.0013 (5)	0.0016 (5)	0.0039 (5)
C8	0.0258 (6)	0.0259 (6)	0.0304 (6)	−0.0036 (5)	−0.0057 (5)	0.0046 (5)
C9	0.0208 (8)	0.0257 (8)	0.0214 (8)	0.000	−0.0004 (6)	0.000
C10	0.0224 (6)	0.0376 (7)	0.0232 (6)	−0.0006 (5)	0.0000 (5)	0.0051 (5)

Geometric parameters (Å, º)

Cl1—C1	1.7384 (14)	C5—C6	1.388 (2)
O1—C7	1.4181 (15)	C5—H5	0.9500
O1—C8	1.4361 (15)	C6—C7	1.5062 (17)
O2—C7	1.4141 (15)	C7—H7	1.0000
O2—C10	1.4402 (15)	C8—C9	1.5272 (16)
C1—C2	1.3906 (18)	C8—H8A	0.9900
C1—C6	1.3921 (17)	C8—H8B	0.9900
C2—C3	1.378 (2)	C9—C8^i	1.5272 (16)
C2—H2	0.9500	C9—C10	1.5293 (16)
C3—C4	1.392 (2)	C9—C10^i	1.5293 (16)
C3—H3	0.9500	C10—H10A	0.9900
C4—C5	1.385 (2)	C10—H10B	0.9900
C4—H4	0.9500
C7—O1—C8	110.41 (9)	O1—C7—C6	106.55 (10)
C7—O2—C10	110.16 (10)	O2—C7—H7	110.2
C2—C1—C6	121.55 (13)	O1—C7—H7	110.2
C2—C1—Cl1	117.40 (10)	C6—C7—H7	110.2
C6—C1—Cl1	121.04 (10)	O1—C8—C9	111.25 (10)
C3—C2—C1	119.41 (12)	O1—C8—H8A	109.4
C3—C2—H2	120.3	C9—C8—H8A	109.4
C1—C2—H2	120.3	O1—C8—H8B	109.4
C2—C3—C4	120.21 (13)	C9—C8—H8B	109.4
C2—C3—H3	119.9	H8A—C8—H8B	108.0
C4—C3—H3	119.9	C8^i—C9—C8	107.86 (14)
C5—C4—C3	119.45 (14)	C8^i—C9—C10	111.27 (7)
C5—C4—H4	120.3	C8—C9—C10	107.75 (7)
C3—C4—H4	120.3	C8^i—C9—C10^i	107.75 (7)
C6—C5—C4	121.57 (12)	C8—C9—C10^i	111.27 (7)
C6—C5—H5	119.2	C10—C9—C10^i	110.92 (16)
C4—C5—H5	119.2	O2—C10—C9	111.10 (9)
C5—C6—C1	117.72 (12)	O2—C10—H10A	109.4
C5—C6—C7	119.39 (11)	C9—C10—H10A	109.4
C1—C6—C7	122.75 (12)	O2—C10—H10B	109.4
O2—C7—O1	110.28 (9)	C9—C10—H10B	109.4
O2—C7—C6	109.32 (10)	H10A—C10—H10B	108.0
C6—C1—C2—C3	2.55 (19)	C8—O1—C7—C6	177.43 (10)
Cl1—C1—C2—C3	−176.83 (11)	C5—C6—C7—O2	−50.34 (15)
C1—C2—C3—C4	0.1 (2)	C1—C6—C7—O2	133.95 (12)
C2—C3—C4—C5	−2.1 (2)	C5—C6—C7—O1	68.83 (15)
C3—C4—C5—C6	1.5 (2)	C1—C6—C7—O1	−106.88 (13)
C4—C5—C6—C1	1.0 (2)	C7—O1—C8—C9	58.27 (13)
C4—C5—C6—C7	−174.90 (13)	O1—C8—C9—C8^i	−171.63 (13)
C2—C1—C6—C5	−3.07 (19)	O1—C8—C9—C10	−51.41 (14)
Cl1—C1—C6—C5	176.29 (10)	O1—C8—C9—C10^i	70.39 (14)
C2—C1—C6—C7	172.71 (12)	C7—O2—C10—C9	−58.74 (14)
Cl1—C1—C6—C7	−7.93 (17)	C8^i—C9—C10—O2	169.66 (10)
C10—O2—C7—O1	64.19 (13)	C8—C9—C10—O2	51.61 (14)
C10—O2—C7—C6	−178.97 (10)	C10^i—C9—C10—O2	−70.41 (9)
C8—O1—C7—O2	−64.03 (13)

Symmetry code: (i) −x+1, y, −z+1/2.