7,14-Bis(4-methoxy-phen-yl)-11,11-dimethyl-1,4,10,12-tetra-oxa-dispiro-[4.2.5.2]penta-decane-9,13-dione.

In the title compound, C(27)H(30)O(8), the cyclo-hexane ring is in a chair conformation, while the five-membered ring adopts an envelope conformation. The 1,3-dioxane ring is oriented with respect to the benzene rings at dihedral angles of 53.38 (3) and 55.31 (3)°, while the dihedral angle between the benzene rings is 71.56 (3)°. In the crystal structure, inter-molecular C-H⋯O inter-actions link the mol-ecules into chains.

Related literature

For general background on Meldrum’s acid, see: Davidson & Bernhard (1948 ▶); Meldrum (1908 ▶); Muller et al. (2005 ▶); Ramachary et al. (2003 ▶); Tietze & Beifuss (1993 ▶); Tietze et al. (2001 ▶). For related structures, see: Chande & Khanwelkar (2005 ▶); Ramachary & Barbas (2004 ▶). For bond-length data, see: Allen et al. (1987 ▶). For ring-puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C27H30O8

M = 482.51

Monoclinic,

a = 9.977 (5) Å

b = 20.162 (9) Å

c = 12.508 (6) Å

β = 94.934 (8)°

V = 2507 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.43 × 0.25 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.961, T max = 0.989

11754 measured reflections

4126 independent reflections

1349 reflections with I > 2σ(I)

R int = 0.104

Refinement

R[F 2 > 2σ(F 2)] = 0.075

wR(F 2) = 0.187

S = 1.01

4126 reflections

316 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809013658/hk2665sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809013658/hk2665Isup2.hkl

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

C27H30O8	F(000) = 1024
Mr = 482.51	Dx = 1.279 Mg m−3
Monoclinic, P21/n	Melting point: 479 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 9.977 (5) Å	Cell parameters from 1366 reflections
b = 20.162 (9) Å	θ = 2.3–19.5°
c = 12.508 (6) Å	µ = 0.09 mm−1
β = 94.934 (8)°	T = 298 K
V = 2507 (2) Å3	Prism, colorless
Z = 4	0.43 × 0.25 × 0.12 mm

Bruker SMART CCD area-detector diffractometer	4126 independent reflections
Radiation source: fine-focus sealed tube	1349 reflections with I > 2σ(I)
graphite	Rint = 0.104
φ and ω scans	θmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.961, Tmax = 0.989	k = −20→24
11754 measured reflections	l = −14→14

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)] = 0.075	H-atom parameters constrained
wR(F2) = 0.187	w = 1/[σ2(Fo2) + (0.055P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
4126 reflections	Δρmax = 0.46 e Å−3
316 parameters	Δρmin = −0.21 e Å−3
Primary atom site location: structure-invariant direct methods

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
O1	−0.0782 (3)	0.1365 (2)	0.3511 (3)	0.0761 (13)
O2	0.0250 (4)	0.1844 (2)	0.2024 (3)	0.0751 (12)
O3	0.0355 (4)	0.10348 (19)	0.4940 (3)	0.0686 (12)
O4	0.2363 (4)	0.19884 (18)	0.2038 (3)	0.0649 (11)
O5	0.4608 (4)	0.1128 (2)	0.5381 (4)	0.1049 (16)
O6	0.5876 (5)	0.1554 (2)	0.4129 (4)	0.1001 (16)
O7	−0.0022 (5)	−0.1063 (2)	0.0771 (3)	0.0887 (14)
O8	−0.1002 (4)	0.4239 (2)	0.4598 (4)	0.0898 (14)
C1	0.1680 (5)	0.1482 (2)	0.3627 (4)	0.0466 (14)
C2	0.2380 (5)	0.1994 (3)	0.4430 (5)	0.0615 (16)
H2	0.2350	0.1788	0.5137	0.074*
C3	0.3789 (6)	0.2090 (3)	0.4312 (5)	0.082 (2)
H3A	0.4153	0.2374	0.4892	0.099*
H3B	0.3872	0.2327	0.3646	0.099*
C4	0.4711 (8)	0.1438 (3)	0.4308 (5)	0.0680 (18)
C5	0.3969 (6)	0.0959 (3)	0.3462 (6)	0.084 (2)
H5A	0.4050	0.1141	0.2753	0.101*
H5B	0.4438	0.0537	0.3498	0.101*
C6	0.2578 (5)	0.0834 (3)	0.3569 (5)	0.0588 (16)
H6	0.2569	0.0637	0.4284	0.071*
C7	0.0383 (5)	0.1274 (3)	0.4064 (5)	0.0528 (15)
C8	0.1480 (6)	0.1791 (2)	0.2534 (5)	0.0475 (14)
C9	−0.0965 (5)	0.1675 (3)	0.2462 (4)	0.0507 (14)
C10	−0.1679 (6)	0.1184 (3)	0.1731 (5)	0.091 (2)
H10A	−0.2520	0.1068	0.2002	0.137*
H10B	−0.1134	0.0794	0.1692	0.137*
H10C	−0.1845	0.1374	0.1029	0.137*
C11	−0.1733 (6)	0.2284 (3)	0.2604 (5)	0.090 (2)
H11A	−0.2563	0.2176	0.2898	0.135*
H11B	−0.1922	0.2498	0.1922	0.135*
H11C	−0.1217	0.2577	0.3084	0.135*
C12	0.1543 (5)	0.2613 (3)	0.4480 (5)	0.0537 (15)
C13	0.1714 (5)	0.3153 (3)	0.3840 (5)	0.0556 (15)
H13	0.2404	0.3148	0.3385	0.067*
C14	0.0903 (6)	0.3702 (3)	0.3850 (5)	0.0606 (16)
H14	0.1028	0.4054	0.3389	0.073*
C15	−0.0101 (6)	0.3731 (3)	0.4544 (5)	0.0615 (16)
C16	−0.0247 (6)	0.3210 (3)	0.5229 (5)	0.0660 (17)
H16	−0.0905	0.3227	0.5712	0.079*
C17	0.0572 (5)	0.2659 (3)	0.5209 (4)	0.0560 (15)
H17	0.0472	0.2314	0.5689	0.067*
C18	−0.1000 (8)	0.4737 (4)	0.3811 (7)	0.134 (3)
H18A	−0.1667	0.5064	0.3936	0.201*
H18B	−0.1202	0.4544	0.3114	0.201*
H18C	−0.0129	0.4942	0.3844	0.201*
C19	0.1895 (5)	0.0320 (3)	0.2828 (5)	0.0516 (15)
C20	0.2011 (5)	0.0315 (3)	0.1736 (5)	0.0571 (15)
H20	0.2529	0.0640	0.1441	0.069*
C21	0.1380 (6)	−0.0158 (3)	0.1067 (5)	0.0685 (17)
H21	0.1504	−0.0159	0.0339	0.082*
C22	0.0572 (6)	−0.0626 (3)	0.1485 (6)	0.0643 (17)
C23	0.0439 (5)	−0.0631 (3)	0.2572 (6)	0.0610 (16)
H23	−0.0086	−0.0955	0.2861	0.073*
C24	0.1071 (5)	−0.0163 (3)	0.3232 (5)	0.0595 (15)
H24	0.0949	−0.0167	0.3960	0.071*
C25	−0.0945 (7)	−0.1527 (3)	0.1126 (6)	0.108 (3)
H25A	−0.1280	−0.1801	0.0535	0.162*
H25B	−0.1680	−0.1296	0.1405	0.162*
H25C	−0.0502	−0.1799	0.1678	0.162*
C26	0.6675 (6)	0.1443 (4)	0.5066 (6)	0.102 (3)
H26A	0.7119	0.1854	0.5290	0.123*
H26B	0.7367	0.1124	0.4926	0.123*
C27	0.5964 (7)	0.1206 (4)	0.5904 (6)	0.115 (3)
H27A	0.5981	0.1523	0.6489	0.138*
H27B	0.6324	0.0786	0.6176	0.138*

	U11	U22	U33	U12	U13	U23
O1	0.037 (2)	0.115 (4)	0.076 (3)	−0.008 (2)	0.002 (2)	0.022 (3)
O2	0.049 (2)	0.113 (4)	0.062 (3)	−0.004 (2)	−0.003 (2)	0.026 (2)
O3	0.076 (3)	0.070 (3)	0.059 (3)	−0.008 (2)	0.000 (2)	0.015 (2)
O4	0.065 (2)	0.064 (3)	0.069 (3)	0.004 (2)	0.023 (2)	0.009 (2)
O5	0.074 (3)	0.096 (4)	0.152 (4)	−0.018 (3)	0.050 (3)	−0.033 (3)
O6	0.082 (3)	0.115 (4)	0.101 (4)	0.007 (3)	−0.004 (3)	−0.004 (3)
O7	0.100 (3)	0.075 (3)	0.088 (3)	−0.023 (3)	−0.005 (3)	−0.022 (3)
O8	0.082 (3)	0.064 (3)	0.127 (4)	0.031 (3)	0.030 (3)	−0.002 (3)
C1	0.043 (3)	0.043 (3)	0.054 (4)	0.007 (3)	0.001 (3)	0.001 (3)
C2	0.064 (4)	0.044 (4)	0.073 (4)	0.002 (3)	−0.014 (3)	−0.017 (3)
C3	0.067 (4)	0.091 (5)	0.089 (5)	0.005 (4)	0.010 (4)	−0.004 (4)
C4	0.080 (5)	0.072 (5)	0.054 (4)	0.006 (4)	0.016 (4)	0.009 (4)
C5	0.068 (4)	0.082 (5)	0.106 (6)	0.008 (4)	0.024 (4)	0.004 (4)
C6	0.058 (4)	0.038 (4)	0.078 (4)	0.012 (3)	−0.008 (3)	−0.012 (3)
C7	0.048 (4)	0.041 (4)	0.070 (4)	0.009 (3)	0.009 (3)	−0.006 (3)
C8	0.048 (3)	0.040 (3)	0.057 (4)	0.003 (3)	0.013 (3)	−0.010 (3)
C9	0.047 (3)	0.056 (4)	0.047 (4)	0.002 (3)	−0.008 (3)	0.006 (3)
C10	0.069 (4)	0.089 (5)	0.113 (6)	−0.012 (4)	−0.012 (4)	−0.024 (4)
C11	0.085 (5)	0.078 (5)	0.105 (6)	0.006 (4)	0.000 (4)	−0.008 (4)
C12	0.049 (3)	0.042 (4)	0.068 (4)	0.004 (3)	−0.004 (3)	−0.012 (3)
C13	0.051 (3)	0.046 (4)	0.069 (4)	−0.006 (3)	−0.004 (3)	−0.008 (3)
C14	0.068 (4)	0.041 (4)	0.074 (4)	−0.004 (3)	0.015 (3)	−0.008 (3)
C15	0.056 (4)	0.048 (4)	0.078 (5)	0.008 (3)	−0.002 (3)	−0.018 (4)
C16	0.065 (4)	0.062 (5)	0.072 (5)	0.006 (4)	0.010 (3)	−0.021 (4)
C17	0.049 (3)	0.057 (4)	0.063 (4)	0.004 (3)	0.006 (3)	−0.002 (3)
C18	0.145 (7)	0.078 (6)	0.182 (9)	0.055 (6)	0.032 (6)	0.026 (6)
C19	0.049 (3)	0.033 (4)	0.073 (5)	0.002 (3)	0.004 (3)	−0.003 (3)
C20	0.060 (4)	0.047 (4)	0.066 (4)	0.003 (3)	0.012 (3)	−0.001 (3)
C21	0.078 (4)	0.058 (4)	0.069 (4)	0.005 (4)	0.003 (4)	−0.016 (4)
C22	0.068 (4)	0.055 (5)	0.068 (5)	−0.001 (4)	−0.002 (4)	−0.020 (4)
C23	0.058 (4)	0.043 (4)	0.081 (5)	−0.003 (3)	0.002 (4)	0.012 (3)
C24	0.071 (4)	0.042 (4)	0.064 (4)	0.001 (3)	−0.004 (3)	−0.002 (3)
C25	0.106 (6)	0.085 (6)	0.133 (7)	−0.011 (5)	0.009 (5)	−0.044 (5)
C26	0.051 (4)	0.174 (8)	0.077 (5)	0.012 (5)	−0.021 (4)	0.000 (5)
C27	0.067 (5)	0.185 (9)	0.091 (6)	−0.014 (5)	−0.008 (4)	0.035 (5)

O1—C7	1.313 (6)	C11—H11A	0.9600
O1—C9	1.451 (6)	C11—H11B	0.9600
O2—C8	1.338 (6)	C11—H11C	0.9600
O2—C9	1.415 (6)	C12—C13	1.371 (7)
O3—C7	1.199 (6)	C12—C17	1.389 (7)
O4—C8	1.188 (5)	C13—C14	1.371 (7)
O5—C27	1.460 (7)	C13—H13	0.9300
O5—C4	1.492 (7)	C14—C15	1.382 (7)
O6—C4	1.225 (7)	C14—H14	0.9300
O6—C26	1.377 (7)	C15—C16	1.372 (8)
O7—C22	1.353 (6)	C16—C17	1.380 (7)
O7—C25	1.410 (7)	C16—H16	0.9300
O8—C15	1.368 (6)	C17—H17	0.9300
O8—C18	1.406 (8)	C18—H18A	0.9600
C1—C8	1.500 (7)	C18—H18B	0.9600
C1—C7	1.507 (7)	C18—H18C	0.9600
C1—C2	1.562 (7)	C19—C20	1.380 (7)
C1—C6	1.590 (6)	C19—C24	1.397 (7)
C2—C3	1.440 (7)	C20—C21	1.384 (7)
C2—C12	1.506 (7)	C20—H20	0.9300
C2—H2	0.9800	C21—C22	1.374 (7)
C3—C4	1.605 (8)	C21—H21	0.9300
C3—H3A	0.9700	C22—C23	1.378 (7)
C3—H3B	0.9700	C23—C24	1.372 (7)
C4—C5	1.570 (8)	C23—H23	0.9300
C5—C6	1.428 (7)	C24—H24	0.9300
C5—H5A	0.9700	C25—H25A	0.9600
C5—H5B	0.9700	C25—H25B	0.9600
C6—C19	1.512 (7)	C25—H25C	0.9600
C6—H6	0.9800	C26—C27	1.400 (8)
C9—C11	1.466 (7)	C26—H26A	0.9700
C9—C10	1.486 (7)	C26—H26B	0.9700
C10—H10A	0.9600	C27—H27A	0.9700
C10—H10B	0.9600	C27—H27B	0.9700
C10—H10C	0.9600
C7—O1—C9	125.0 (4)	C9—C11—H11C	109.5
C8—O2—C9	125.3 (4)	H11A—C11—H11C	109.5
C27—O5—C4	103.0 (5)	H11B—C11—H11C	109.5
C4—O6—C26	107.6 (6)	C13—C12—C17	117.3 (5)
C22—O7—C25	119.0 (5)	C13—C12—C2	122.5 (5)
C15—O8—C18	117.3 (5)	C17—C12—C2	120.2 (6)
C8—C1—C7	113.3 (4)	C12—C13—C14	122.2 (5)
C8—C1—C2	109.2 (4)	C12—C13—H13	118.9
C7—C1—C2	107.5 (4)	C14—C13—H13	118.9
C8—C1—C6	109.3 (4)	C13—C14—C15	120.0 (6)
C7—C1—C6	107.0 (4)	C13—C14—H14	120.0
C2—C1—C6	110.5 (4)	C15—C14—H14	120.0
C3—C2—C12	116.3 (5)	O8—C15—C16	115.9 (6)
C3—C2—C1	114.2 (5)	O8—C15—C14	125.3 (6)
C12—C2—C1	110.8 (4)	C16—C15—C14	118.8 (6)
C3—C2—H2	104.7	C15—C16—C17	120.7 (6)
C12—C2—H2	104.7	C15—C16—H16	119.7
C1—C2—H2	104.7	C17—C16—H16	119.7
C2—C3—C4	117.1 (6)	C16—C17—C12	120.9 (6)
C2—C3—H3A	108.0	C16—C17—H17	119.6
C4—C3—H3A	108.0	C12—C17—H17	119.6
C2—C3—H3B	108.0	O8—C18—H18A	109.5
C4—C3—H3B	108.0	O8—C18—H18B	109.5
H3A—C3—H3B	107.3	H18A—C18—H18B	109.5
O6—C4—O5	112.6 (6)	O8—C18—H18C	109.5
O6—C4—C5	113.2 (6)	H18A—C18—H18C	109.5
O5—C4—C5	106.5 (5)	H18B—C18—H18C	109.5
O6—C4—C3	113.4 (6)	C20—C19—C24	117.1 (5)
O5—C4—C3	104.8 (5)	C20—C19—C6	122.6 (5)
C5—C4—C3	105.6 (5)	C24—C19—C6	120.3 (6)
C6—C5—C4	116.8 (5)	C19—C20—C21	122.0 (6)
C6—C5—H5A	108.1	C19—C20—H20	119.0
C4—C5—H5A	108.1	C21—C20—H20	119.0
C6—C5—H5B	108.1	C22—C21—C20	119.7 (6)
C4—C5—H5B	108.1	C22—C21—H21	120.1
H5A—C5—H5B	107.3	C20—C21—H21	120.1
C5—C6—C19	117.0 (5)	O7—C22—C21	115.8 (6)
C5—C6—C1	114.6 (5)	O7—C22—C23	124.9 (6)
C19—C6—C1	111.4 (4)	C21—C22—C23	119.3 (6)
C5—C6—H6	104.0	C24—C23—C22	120.7 (6)
C19—C6—H6	104.0	C24—C23—H23	119.6
C1—C6—H6	104.0	C22—C23—H23	119.6
O3—C7—O1	116.7 (5)	C23—C24—C19	121.1 (6)
O3—C7—C1	122.1 (5)	C23—C24—H24	119.4
O1—C7—C1	121.2 (5)	C19—C24—H24	119.4
O4—C8—O2	114.5 (5)	O7—C25—H25A	109.5
O4—C8—C1	124.6 (5)	O7—C25—H25B	109.5
O2—C8—C1	120.8 (5)	H25A—C25—H25B	109.5
O2—C9—O1	114.1 (4)	O7—C25—H25C	109.5
O2—C9—C11	108.6 (5)	H25A—C25—H25C	109.5
O1—C9—C11	106.1 (5)	H25B—C25—H25C	109.5
O2—C9—C10	107.7 (5)	O6—C26—C27	113.5 (6)
O1—C9—C10	106.6 (5)	O6—C26—H26A	108.9
C11—C9—C10	113.8 (5)	C27—C26—H26A	108.9
C9—C10—H10A	109.5	O6—C26—H26B	108.9
C9—C10—H10B	109.5	C27—C26—H26B	108.9
H10A—C10—H10B	109.5	H26A—C26—H26B	107.7
C9—C10—H10C	109.5	C26—C27—O5	102.1 (5)
H10A—C10—H10C	109.5	C26—C27—H27A	111.3
H10B—C10—H10C	109.5	O5—C27—H27A	111.3
C9—C11—H11A	109.5	C26—C27—H27B	111.3
C9—C11—H11B	109.5	O5—C27—H27B	111.3
H11A—C11—H11B	109.5	H27A—C27—H27B	109.2

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O4i	0.93	2.53	3.449 (3)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16⋯O4i	0.93	2.53	3.449 (3)	168

Symmetry code: (i) .