7,14-Bis(4-methoxy­phen­yl)-11,11-dimethyl-1,4,10,12-tetra­oxa­dispiro­[4.2.5.2]penta­decane-9,13-dione

Zhang, J.; Yan, S.; Ding, J.

doi:10.1107/S1600536809013658

organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page o1076

doi:10.1107/S1600536809013658

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7,14-Bis(4-methoxyphenyl)-11,11-dimethyl-1,4,10,12-tetraoxadispiro[4.2.5.2]pentadecane-9,13-dione

Jinpeng Zhang,^a ^* Shu Yan ^b and Jie Ding ^b

^aDepartment of Public Health, Xuzhou Medical College, Xuzhou 221000, People's Republic of China, and ^bCollege of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou 221116, People's Republic of China
^*Correspondence e-mail: yanshu126@126.com

(Received 10 April 2009; accepted 11 April 2009; online 18 April 2009)

In the title compound, C₂₇H₃₀O₈, the cyclohexane 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, intermolecular C—H⋯O interactions link the molecules 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_r = 482.51
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.075
wR(F²) = 0.187
S = 1.01
4126 reflections
316 parameters
H-atom parameters constrained
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.21 e Å⁻³

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) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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.

Supporting information

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

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

checkCIF report

Comment top

Over the past few decades, Meldrum's acid (2,2-dimethyl-1,3-dioxane-4,6-dione) (Tietze & Beifuss, 1993; Tietze et al., 2001) has been used as a versatile organic reagent (Ramachary et al., 2003; Muller et al., 2005) and its derivatives are very useful building blocks in synthetic organic chemistry (Davidson & Bernhard, 1948; Meldrum, 1908). Spirocyclic compounds including a Meldrum's acid unit are attractive intermediates in the syntheses of natural products and in medicinal chemistry. Thus, the synthesis of new highly substituted spiro ring system with a Meldrum's acid unit has attracted widespread attention (Ramachary & Barbas, 2004; Chande & Khanwelkar, 2005). We report herein the crystal structure of the title compound.

In the molecule of the title compound (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Ring A (C1-C6) is not planar, having total puckering amplitude, Q_T, of 0.500 (2) Å and chair conformation [ϕ = 7.64 (3) and θ = 175.56 (3) °] (Cremer & Pople, 1975). Rings B (O1/O2/C1/C7-C9), D (C12-C17) and E (C19-C24) are, of course, planar, and they are oriented at dihedral angles of B/D = 53.38 (3), B/E = 55.31 (3) and D/E = 71.56 (3) °. Ring C (O5/O6/C4/C26/C27) adopts envelope conformation, with atom O5 displaced by 0.153 (3) Å from the plane of the other ring atoms.

In the crystal structure, intermolecular C-H···O interactions (Table 1) link the molecules into chains (Fig. 2), in which they may be effective in the stabilization of the structure.

Related literature top

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 top

The title compound was prepared by the reaction of of 1,2-diarylidenehydrazine (2 mmol), Meldrum's acid (5 mmol), HOAc (4 ml) and and ethane-1,2-diol (8 ml).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A partial packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.

7,14-Bis(4-methoxyphenyl)-11,11-dimethyl-1,4,10,12- tetraoxadispiro[4.2.5.2]pentadecane-9,13-dione top

Crystal data top

C₂₇H₃₀O₈	F(000) = 1024
M_r = 482.51	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.055P)²] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
4126 reflections	Δρ_max = 0.46 e Å⁻³
316 parameters	Δρ_min = −0.21 e Å⁻³
Primary atom site location: structure-invariant direct methods

Crystal data top

C₂₇H₃₀O₈	V = 2507 (2) Å³
M_r = 482.51	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.977 (5) Å	µ = 0.09 mm⁻¹
b = 20.162 (9) Å	T = 298 K
c = 12.508 (6) Å	0.43 × 0.25 × 0.12 mm
β = 94.934 (8)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4126 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1349 reflections with I > 2σ(I)
T_min = 0.961, T_max = 0.989	R_int = 0.104
11754 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.075	316 parameters
wR(F²) = 0.187	H-atom parameters constrained
S = 1.01	Δρ_max = 0.46 e Å⁻³
4126 reflections	Δρ_min = −0.21 e Å⁻³

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
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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) x−1/2, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₇H₃₀O₈
M_r	482.51
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	9.977 (5), 20.162 (9), 12.508 (6)
β (°)	94.934 (8)
V (Å³)	2507 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.43 × 0.25 × 0.12

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.961, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	11754, 4126, 1349
R_int	0.104
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.075, 0.187, 1.01
No. of reflections	4126
No. of parameters	316
No. of restraints	?
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.21

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) x−1/2, −y+1/2, z+1/2.

Acknowledgements

The authors thank the National Natural Science Foundation of China (grant No. 20672090), the Natural Science Foundation of Jiangsu Province (grant No. BK2006033) and the Graduate Foundation of Xuzhou Normal University (grant No. 08YLB028) for financial support.

References

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

7,14-Bis(4-meth­oxy­phen­yl)-11,11-di­methyl-1,4,10,12-tetra­oxa­di­spiro­[4.2.5.2]penta­decane-9,13-dione

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

7,14-Bis(4-methoxyphenyl)-11,11-dimethyl-1,4,10,12-tetraoxadispiro[4.2.5.2]pentadecane-9,13-dione