3,9-Di-1-naphthyl-2,4,8,10-tetra­oxa­spiro­[5.5]undeca­ne

Zhang, X.; Cui, Y.; Yu, B.; Sun, X.; Chen, Q.

doi:10.1107/S1600536810014741

3,9-Di-1-naphthyl-2,4,8,10-tetraoxaspiro[5.5]undecane

X. Zhang, Y. Cui, B. Yu, X. Sun and Q. Chen

In the title compound, C₂₇H₂₄O₄, the 1,3-dioxane rings have chair conformations. The molecule has non-crystallographic twofold rotation symmetry. The dihedral angle between the naphthalene ring systems is 17.96(4)° In the crystal structure, weak intermolecular C-H

interactions contribute to the crystal packing.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810014741/si2258sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536810014741/si2258Isup2.hkl Contains datablock I

CCDC reference: 778071

checkCIF report

Key indicators

Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.003 Å
R factor = 0.042
wR factor = 0.158
Data-to-parameter ratio = 14.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         13
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          1
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600          3

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

The title compound is an important intermediate in the synthesis of pesticides. Several related structures were synthesized and reported (Wang et al.,2006; Mihis et al.,2008; Shi et al.,2009). The X-ray structural analysis confirmed the assignment of the structure of the title compound from spectroscopic data. The molecular structure is depicted in Fig. 1. The title molecule has a non-crystallographic twofold rotation symmetry. In the molecules, the naphthalene planes make a dihedral angle of 17.96 (4) °. Weak intermolecular C–H···π interactions contribute to the crystal packing (Table 1).

Related literature top

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 top

Pentaerythritol (0.22 g, 1.6 mmol), α-naphthaldehyde (0.5 g, 3.2 mmol), p-toluene sulphonic acid (0.02 g, 0.12 mmol) and dimethylbenzene (10 ml) were heated for six hours. The mixture was cooled and then filtered. The organic phase was evaporated on a rotary evaporator and the resulting solid was recrystallized in ethyl acetate, yielding the title compound (0.53 g, 80%); m.p. 445-446 K.

Structure description top

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).

Computing details top

Data collection: APEX2 (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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

Fig. 1. Molecular structure of the title compound with the atom labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are drawn as small spheres of arbitrary radii.

3,9-Di-1-naphthyl-2,4,8,10-tetraoxaspiro[5.5]undecane top

Crystal data top

C₂₇H₂₄O₄	F(000) = 872
M_r = 412.46	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.1P)² + 0.1334P] where P = (F_o² + 2F_c²)/3
4067 reflections	(Δ/σ)_max = 0.001
280 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₂₇H₂₄O₄	V = 2077.1 (4) Å³
M_r = 412.46	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.9040 (15) Å	µ = 0.09 mm⁻¹
b = 5.7761 (6) Å	T = 295 K
c = 24.238 (2) Å	0.22 × 0.21 × 0.19 mm
β = 95.447 (2)°

Data collection top

Bruker APEXII CCD diffractometer	4067 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2003)	2961 reflections with I > 2σ(I)
T_min = 0.981, T_max = 0.984	R_int = 0.024
11731 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.158	H-atom parameters constrained
S = 1.03	Δρ_max = 0.16 e Å⁻³
4067 reflections	Δρ_min = −0.17 e Å⁻³
280 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) x, y−1, z; (ii) −x, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₇H₂₄O₄
M_r	412.46
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	14.9040 (15), 5.7761 (6), 24.238 (2)
β (°)	95.447 (2)
V (Å³)	2077.1 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.22 × 0.21 × 0.19

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2003)
T_min, T_max	0.981, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	11731, 4067, 2961
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.158, 1.03
No. of reflections	4067
No. of parameters	280
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.17

Computer programs: APEX2 (Bruker, 2003), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).