3,9-Di-1-naphthyl-2,4,8,10-tetra-oxa-spiro-[5.5]undeca-ne.

In the title compound, C(27)H(24)O(4), the 1,3-dioxane rings have chair conformations. The mol-ecule has non-crystallographic twofold rotation symmetry. The dihedral angle between the naphthalene ring systems is 17.96(4)° In the crystal structure, weak inter-molecular C-H⋯π inter-actions contribute to the crystal packing.

Related literature

For a related 3,9-diphenyl structure, see: Wang et al. (2006 ▶). For other oxaspiro structures, see: Mihis et al. (2008 ▶); Shi et al. (2009 ▶).

Experimental

Crystal data

C27H24O4

M = 412.46

Monoclinic,

a = 14.9040 (15) Å

b = 5.7761 (6) Å

c = 24.238 (2) Å

β = 95.447 (2)°

V = 2077.1 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 295 K

0.22 × 0.21 × 0.19 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2003 ▶) T min = 0.981, T max = 0.984

11731 measured reflections

4067 independent reflections

2961 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.158

S = 1.03

4067 reflections

280 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); 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: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810014741/si2258sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810014741/si2258Isup2.hkl

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

C27H24O4	F(000) = 872
Mr = 412.46	Dx = 1.319 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.9040 (15) Å	Cell parameters from 4101 reflections
b = 5.7761 (6) Å	θ = 2.8–28.9°
c = 24.238 (2) Å	µ = 0.09 mm−1
β = 95.447 (2)°	T = 295 K
V = 2077.1 (4) Å3	Block, colorless
Z = 4	0.22 × 0.21 × 0.19 mm

Bruker APEXII CCD diffractometer	4067 independent reflections
Radiation source: fine-focus sealed tube	2961 reflections with I > 2σ(I)
graphite	Rint = 0.024
φ and ω scans	θmax = 26.0°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −18→16
Tmin = 0.981, Tmax = 0.984	k = −6→7
11731 measured reflections	l = −29→29

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.158	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.1P)2 + 0.1334P] where P = (Fo2 + 2Fc2)/3
4067 reflections	(Δ/σ)max = 0.001
280 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.13414 (8)	0.84377 (18)	0.45655 (4)	0.0446 (3)
O2	0.22638 (8)	0.6064 (2)	0.40974 (4)	0.0515 (3)
O3	0.26584 (7)	0.18521 (18)	0.56082 (5)	0.0480 (3)
O4	0.36401 (8)	0.4833 (2)	0.54471 (5)	0.0547 (3)
C1	0.34069 (15)	−0.1745 (4)	0.71697 (8)	0.0678 (6)
H1	0.2942	−0.1732	0.7400	0.081*
C2	0.40805 (16)	−0.3418 (4)	0.72465 (9)	0.0720 (6)
H2	0.4063	−0.4513	0.7527	0.086*
C3	0.47631 (14)	−0.3452 (3)	0.69128 (9)	0.0650 (6)
H3	0.5207	−0.4584	0.6965	0.078*
C4	0.48080 (12)	−0.1802 (3)	0.64906 (8)	0.0539 (5)
C5	0.55262 (13)	−0.1798 (4)	0.61468 (9)	0.0700 (6)
H5	0.5969	−0.2934	0.6193	0.084*
C6	0.55731 (14)	−0.0168 (4)	0.57552 (10)	0.0790 (7)
H6	0.6062	−0.0149	0.5543	0.095*
C7	0.48923 (13)	0.1507 (4)	0.56622 (9)	0.0653 (5)
H7	0.4933	0.2611	0.5386	0.078*
C8	0.41737 (12)	0.1540 (3)	0.59693 (7)	0.0488 (4)
C9	0.41222 (11)	−0.0103 (3)	0.64054 (7)	0.0463 (4)
C10	0.34223 (12)	−0.0132 (3)	0.67623 (7)	0.0556 (5)
H10	0.2966	0.0970	0.6717	0.067*
C11	0.34087 (11)	0.3197 (3)	0.58327 (7)	0.0460 (4)
H11	0.3259	0.3980	0.6171	0.055*
C12	0.18859 (11)	0.3248 (3)	0.54602 (7)	0.0488 (4)
H12A	0.1679	0.3917	0.5793	0.059*
H12B	0.1406	0.2283	0.5288	0.059*
C13	0.29204 (12)	0.6434 (3)	0.53143 (7)	0.0523 (5)
H13A	0.3104	0.7575	0.5054	0.063*
H13B	0.2784	0.7239	0.5648	0.063*
C14	0.20848 (10)	0.5180 (3)	0.50633 (6)	0.0406 (4)
C15	0.12684 (12)	0.6778 (3)	0.49917 (7)	0.0495 (4)
H15A	0.0729	0.5857	0.4904	0.059*
H15B	0.1207	0.7576	0.5338	0.059*
C16	0.22281 (12)	0.4224 (3)	0.44935 (7)	0.0506 (4)
H16A	0.2787	0.3353	0.4515	0.061*
H16B	0.1739	0.3179	0.4373	0.061*
C17	0.14617 (11)	0.7325 (3)	0.40554 (6)	0.0413 (4)
H17	0.0954	0.6281	0.3956	0.050*
C18	0.14747 (11)	0.9196 (3)	0.36260 (6)	0.0430 (4)
C19	0.22421 (13)	0.9714 (3)	0.33883 (7)	0.0554 (5)
H19	0.2755	0.8813	0.3470	0.066*
C20	0.22692 (15)	1.1598 (4)	0.30208 (8)	0.0674 (6)
H20	0.2796	1.1916	0.2858	0.081*
C21	0.15360 (16)	1.2942 (4)	0.29038 (7)	0.0670 (6)
H21	0.1569	1.4206	0.2669	0.080*
C22	0.07234 (14)	1.2462 (3)	0.31316 (7)	0.0535 (5)
C23	0.06793 (12)	1.0532 (3)	0.34917 (6)	0.0442 (4)
C24	−0.01615 (12)	1.0029 (3)	0.36927 (7)	0.0543 (5)
H24	−0.0207	0.8775	0.3929	0.065*
C25	−0.09045 (14)	1.1344 (4)	0.35467 (8)	0.0687 (6)
H25	−0.1452	1.0951	0.3676	0.082*
C26	−0.08524 (17)	1.3280 (4)	0.32048 (9)	0.0761 (7)
H26	−0.1359	1.4193	0.3114	0.091*
C27	−0.00558 (17)	1.3820 (4)	0.30050 (8)	0.0711 (6)
H27	−0.0024	1.5114	0.2780	0.085*

	U11	U22	U33	U12	U13	U23
O1	0.0659 (7)	0.0329 (6)	0.0345 (6)	0.0103 (5)	0.0018 (5)	0.0004 (4)
O2	0.0625 (8)	0.0500 (7)	0.0416 (6)	0.0150 (6)	0.0034 (5)	−0.0012 (5)
O3	0.0504 (7)	0.0305 (6)	0.0603 (7)	0.0003 (5)	−0.0103 (5)	0.0055 (5)
O4	0.0552 (7)	0.0417 (7)	0.0639 (8)	−0.0075 (5)	−0.0122 (6)	0.0112 (6)
C1	0.0774 (14)	0.0711 (14)	0.0534 (11)	−0.0021 (11)	−0.0019 (9)	0.0115 (10)
C2	0.0816 (15)	0.0645 (14)	0.0651 (12)	−0.0064 (11)	−0.0180 (11)	0.0232 (10)
C3	0.0643 (12)	0.0498 (11)	0.0750 (13)	−0.0001 (9)	−0.0245 (10)	0.0110 (9)
C4	0.0495 (10)	0.0471 (10)	0.0603 (10)	−0.0024 (8)	−0.0204 (8)	0.0018 (8)
C5	0.0489 (11)	0.0699 (14)	0.0879 (15)	0.0110 (10)	−0.0104 (10)	0.0089 (12)
C6	0.0557 (12)	0.0890 (17)	0.0927 (16)	0.0088 (12)	0.0089 (11)	0.0187 (14)
C7	0.0582 (12)	0.0679 (13)	0.0684 (12)	−0.0001 (10)	−0.0016 (9)	0.0152 (10)
C8	0.0509 (10)	0.0427 (9)	0.0494 (9)	−0.0029 (8)	−0.0131 (7)	−0.0005 (7)
C9	0.0490 (9)	0.0402 (9)	0.0458 (9)	−0.0050 (7)	−0.0161 (7)	−0.0032 (7)
C10	0.0614 (11)	0.0527 (11)	0.0502 (10)	0.0036 (9)	−0.0078 (8)	0.0022 (8)
C11	0.0553 (10)	0.0358 (9)	0.0443 (8)	−0.0043 (7)	−0.0088 (7)	−0.0008 (7)
C12	0.0504 (10)	0.0360 (9)	0.0587 (10)	0.0043 (7)	−0.0019 (8)	0.0086 (7)
C13	0.0690 (12)	0.0320 (9)	0.0525 (10)	−0.0035 (8)	−0.0110 (8)	0.0037 (7)
C14	0.0500 (9)	0.0295 (8)	0.0410 (8)	0.0029 (7)	−0.0025 (7)	−0.0009 (6)
C15	0.0640 (11)	0.0422 (9)	0.0428 (9)	0.0111 (8)	0.0075 (8)	0.0072 (7)
C16	0.0658 (11)	0.0363 (9)	0.0476 (9)	0.0127 (8)	−0.0055 (8)	−0.0054 (7)
C17	0.0498 (9)	0.0358 (8)	0.0369 (8)	0.0040 (7)	−0.0028 (6)	−0.0062 (6)
C18	0.0547 (10)	0.0423 (9)	0.0307 (7)	−0.0015 (8)	−0.0035 (6)	−0.0065 (7)
C19	0.0613 (11)	0.0614 (12)	0.0429 (9)	−0.0007 (9)	0.0020 (8)	−0.0036 (8)
C20	0.0767 (14)	0.0766 (15)	0.0497 (11)	−0.0168 (12)	0.0099 (10)	0.0028 (10)
C21	0.1016 (17)	0.0567 (12)	0.0406 (9)	−0.0183 (12)	−0.0041 (10)	0.0068 (8)
C22	0.0810 (13)	0.0434 (9)	0.0326 (8)	0.0004 (9)	−0.0125 (8)	−0.0030 (7)
C23	0.0622 (10)	0.0398 (9)	0.0283 (7)	0.0006 (8)	−0.0074 (7)	−0.0060 (6)
C24	0.0612 (11)	0.0571 (11)	0.0429 (9)	0.0068 (9)	−0.0034 (8)	−0.0002 (8)
C25	0.0664 (13)	0.0836 (15)	0.0534 (11)	0.0179 (11)	−0.0090 (9)	−0.0104 (10)
C26	0.0882 (16)	0.0758 (16)	0.0589 (12)	0.0347 (13)	−0.0216 (11)	−0.0084 (11)
C27	0.1127 (19)	0.0499 (11)	0.0449 (10)	0.0161 (12)	−0.0234 (11)	0.0012 (9)

O1—C17	1.4198 (18)	C12—H12B	0.9700
O1—C15	1.4211 (19)	C13—C14	1.517 (2)
O2—C17	1.3954 (18)	C13—H13A	0.9700
O2—C16	1.437 (2)	C13—H13B	0.9700
O3—C12	1.4233 (18)	C14—C16	1.521 (2)
O3—C11	1.4265 (19)	C14—C15	1.524 (2)
O4—C11	1.395 (2)	C15—H15A	0.9700
O4—C13	1.429 (2)	C15—H15B	0.9700
C1—C10	1.360 (3)	C16—H16A	0.9700
C1—C2	1.393 (3)	C16—H16B	0.9700
C1—H1	0.9300	C17—C18	1.502 (2)
C2—C3	1.359 (3)	C17—H17	0.9800
C2—H2	0.9300	C18—C19	1.362 (2)
C3—C4	1.404 (3)	C18—C23	1.426 (2)
C3—H3	0.9300	C19—C20	1.409 (3)
C4—C5	1.418 (3)	C19—H19	0.9300
C4—C9	1.418 (2)	C20—C21	1.349 (3)
C5—C6	1.343 (3)	C20—H20	0.9300
C5—H5	0.9300	C21—C22	1.406 (3)
C6—C7	1.405 (3)	C21—H21	0.9300
C6—H6	0.9300	C22—C27	1.411 (3)
C7—C8	1.361 (3)	C22—C23	1.421 (2)
C7—H7	0.9300	C23—C24	1.417 (2)
C8—C9	1.428 (2)	C24—C25	1.362 (3)
C8—C11	1.502 (2)	C24—H24	0.9300
C9—C10	1.417 (3)	C25—C26	1.398 (3)
C10—H10	0.9300	C25—H25	0.9300
C11—H11	0.9800	C26—C27	1.360 (3)
C12—C14	1.521 (2)	C26—H26	0.9300
C12—H12A	0.9700	C27—H27	0.9300
C17—O1—C15	110.63 (12)	C13—C14—C16	110.89 (14)
C17—O2—C16	110.43 (13)	C12—C14—C16	111.14 (13)
C12—O3—C11	111.94 (13)	C13—C14—C15	111.88 (14)
C11—O4—C13	111.16 (14)	C12—C14—C15	108.36 (13)
C10—C1—C2	120.7 (2)	C16—C14—C15	107.20 (12)
C10—C1—H1	119.6	O1—C15—C14	112.09 (13)
C2—C1—H1	119.6	O1—C15—H15A	109.2
C3—C2—C1	120.09 (19)	C14—C15—H15A	109.2
C3—C2—H2	120.0	O1—C15—H15B	109.2
C1—C2—H2	120.0	C14—C15—H15B	109.2
C2—C3—C4	120.93 (19)	H15A—C15—H15B	107.9
C2—C3—H3	119.5	O2—C16—C14	110.83 (13)
C4—C3—H3	119.5	O2—C16—H16A	109.5
C3—C4—C5	121.35 (18)	C14—C16—H16A	109.5
C3—C4—C9	119.49 (19)	O2—C16—H16B	109.5
C5—C4—C9	119.16 (17)	C14—C16—H16B	109.5
C6—C5—C4	120.62 (19)	H16A—C16—H16B	108.1
C6—C5—H5	119.7	O2—C17—O1	110.54 (11)
C4—C5—H5	119.7	O2—C17—C18	111.03 (13)
C5—C6—C7	120.7 (2)	O1—C17—C18	106.80 (12)
C5—C6—H6	119.6	O2—C17—H17	109.5
C7—C6—H6	119.6	O1—C17—H17	109.5
C8—C7—C6	121.05 (19)	C18—C17—H17	109.5
C8—C7—H7	119.5	C19—C18—C23	119.86 (16)
C6—C7—H7	119.5	C19—C18—C17	121.19 (15)
C7—C8—C9	119.73 (16)	C23—C18—C17	118.84 (14)
C7—C8—C11	120.58 (16)	C18—C19—C20	120.83 (18)
C9—C8—C11	119.59 (16)	C18—C19—H19	119.6
C10—C9—C4	117.72 (16)	C20—C19—H19	119.6
C10—C9—C8	123.65 (16)	C21—C20—C19	120.41 (19)
C4—C9—C8	118.63 (17)	C21—C20—H20	119.8
C1—C10—C9	121.03 (18)	C19—C20—H20	119.8
C1—C10—H10	119.5	C20—C21—C22	121.00 (18)
C9—C10—H10	119.5	C20—C21—H21	119.5
O4—C11—O3	110.36 (12)	C22—C21—H21	119.5
O4—C11—C8	110.41 (14)	C21—C22—C27	121.80 (19)
O3—C11—C8	106.74 (13)	C21—C22—C23	119.21 (18)
O4—C11—H11	109.8	C27—C22—C23	118.98 (19)
O3—C11—H11	109.8	C24—C23—C22	117.77 (16)
C8—C11—H11	109.8	C24—C23—C18	123.62 (15)
O3—C12—C14	111.92 (13)	C22—C23—C18	118.60 (16)
O3—C12—H12A	109.2	C25—C24—C23	121.35 (19)
C14—C12—H12A	109.2	C25—C24—H24	119.3
O3—C12—H12B	109.2	C23—C24—H24	119.3
C14—C12—H12B	109.2	C24—C25—C26	120.7 (2)
H12A—C12—H12B	107.9	C24—C25—H25	119.7
O4—C13—C14	110.57 (13)	C26—C25—H25	119.7
O4—C13—H13A	109.5	C27—C26—C25	119.58 (19)
C14—C13—H13A	109.5	C27—C26—H26	120.2
O4—C13—H13B	109.5	C25—C26—H26	120.2
C14—C13—H13B	109.5	C26—C27—C22	121.57 (19)
H13A—C13—H13B	108.1	C26—C27—H27	119.2
C13—C14—C12	107.37 (13)	C22—C27—H27	119.2
C10—C1—C2—C3	0.0 (3)	C17—O1—C15—C14	56.96 (17)
C1—C2—C3—C4	0.6 (3)	C13—C14—C15—O1	70.48 (17)
C2—C3—C4—C5	178.8 (2)	C12—C14—C15—O1	−171.34 (13)
C2—C3—C4—C9	−1.1 (3)	C16—C14—C15—O1	−51.30 (18)
C3—C4—C5—C6	−178.1 (2)	C17—O2—C16—C14	−59.81 (17)
C9—C4—C5—C6	1.9 (3)	C13—C14—C16—O2	−70.38 (17)
C4—C5—C6—C7	−2.7 (4)	C12—C14—C16—O2	170.25 (13)
C5—C6—C7—C8	0.7 (3)	C15—C14—C16—O2	52.01 (18)
C6—C7—C8—C9	2.1 (3)	C16—O2—C17—O1	63.95 (16)
C6—C7—C8—C11	−174.38 (18)	C16—O2—C17—C18	−177.72 (12)
C3—C4—C9—C10	1.0 (2)	C15—O1—C17—O2	−62.50 (17)
C5—C4—C9—C10	−178.95 (17)	C15—O1—C17—C18	176.62 (13)
C3—C4—C9—C8	−179.18 (15)	O2—C17—C18—C19	−9.1 (2)
C5—C4—C9—C8	0.9 (2)	O1—C17—C18—C19	111.48 (16)
C7—C8—C9—C10	177.00 (17)	O2—C17—C18—C23	174.59 (12)
C11—C8—C9—C10	−6.5 (2)	O1—C17—C18—C23	−64.84 (17)
C7—C8—C9—C4	−2.8 (2)	C23—C18—C19—C20	1.7 (2)
C11—C8—C9—C4	173.70 (14)	C17—C18—C19—C20	−174.60 (15)
C2—C1—C10—C9	−0.1 (3)	C18—C19—C20—C21	0.9 (3)
C4—C9—C10—C1	−0.4 (2)	C19—C20—C21—C22	−1.8 (3)
C8—C9—C10—C1	179.76 (17)	C20—C21—C22—C27	−178.67 (17)
C13—O4—C11—O3	62.51 (17)	C20—C21—C22—C23	0.2 (3)
C13—O4—C11—C8	−179.72 (12)	C21—C22—C23—C24	−176.99 (15)
C12—O3—C11—O4	−59.83 (17)	C27—C22—C23—C24	1.9 (2)
C12—O3—C11—C8	−179.84 (13)	C21—C22—C23—C18	2.3 (2)
C7—C8—C11—O4	−11.1 (2)	C27—C22—C23—C18	−178.80 (14)
C9—C8—C11—O4	172.40 (13)	C19—C18—C23—C24	176.01 (15)
C7—C8—C11—O3	108.84 (19)	C17—C18—C23—C24	−7.6 (2)
C9—C8—C11—O3	−67.62 (18)	C19—C18—C23—C22	−3.2 (2)
C11—O3—C12—C14	55.23 (17)	C17—C18—C23—C22	173.15 (13)
C11—O4—C13—C14	−60.70 (17)	C22—C23—C24—C25	0.0 (2)
O4—C13—C14—C12	53.24 (18)	C18—C23—C24—C25	−179.21 (16)
O4—C13—C14—C16	−68.36 (17)	C23—C24—C25—C26	−1.8 (3)
O4—C13—C14—C15	172.01 (13)	C24—C25—C26—C27	1.6 (3)
O3—C12—C14—C13	−51.13 (18)	C25—C26—C27—C22	0.4 (3)
O3—C12—C14—C16	70.32 (17)	C21—C22—C27—C26	176.72 (19)
O3—C12—C14—C15	−172.14 (13)	C23—C22—C27—C26	−2.2 (3)

Cg5 and Cg6 are the centroids of the C18–C23 and C22–C27 naphthyl rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16B···Cg5i	0.97	2.95	3.5827 (19)	124
C27—H27···Cg6ii	0.93	2.94	3.754 (2)	147

Table 1

Hydrogen-bond geometry (Å, °)

Cg5 and Cg6 are the centroids of the C18–C23 and C22–C27 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16B⋯Cg5i	0.97	2.95	3.5827 (19)	124
C27—H27⋯Cg6ii	0.93	2.94	3.754 (2)	147

Symmetry codes: (i) ; (ii) .