3-[(5-Methyl-furan-2-yl)methyl-ene]-1,5-dioxaspiro-[5.5]undecane-2,4-dione.

There are two crystallographically independent mol-ecules in the asymmetric unit of the title compound, C(15)H(16)O(5). In each, the 1,3-dioxane ring is in an envelope conformation with the C atom common to the cyclo-hexane ring forming the flap. The dihedral angles between the five essentially planar [maximum deviations from the least-squares planes of 0.049 (3) and 0.042 (3) Å] atoms of the 1,3-dioxane ring and the furan ring in the two mol-ecules are 7.15 (1) and 6.80 (1)°. The crystal structure is stabilized by weak inter-molecular C-H⋯O hydrogen bonds.

Related literature

For background to the applications of spiro compounds, see: Yaozhong et al. (1998 ▶); Lian et al. (2008 ▶); Wei et al. (2008 ▶). For the crystal structure of 3-(furan-2-ylmethyl­ene)-1,5-dioxa­spiro­[5.5]undecane-2,4-dione, see: Zeng & Jian (2009 ▶).

Experimental

Crystal data

C15H16O5

M = 276.28

Monoclinic,

a = 19.314 (4) Å

b = 6.8289 (14) Å

c = 20.468 (4) Å

β = 97.04 (3)°

V = 2679.2 (9) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.22 × 0.18 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.978, T max = 0.985

21978 measured reflections

6028 independent reflections

3716 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.198

S = 1.02

6028 reflections

363 parameters

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.36 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to refine structure: SHELXS97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680902947X/lh2861sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680902947X/lh2861Isup2.hkl

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

C15H16O5	F(000) = 1168
Mr = 276.28	Dx = 1.370 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3716 reflections
a = 19.314 (4) Å	θ = 3.1–27.5°
b = 6.8289 (14) Å	µ = 0.10 mm−1
c = 20.468 (4) Å	T = 293 K
β = 97.04 (3)°	Block, yellow
V = 2679.2 (9) Å3	0.22 × 0.18 × 0.15 mm
Z = 8

Bruker SMART CCD area-detector diffractometer	6028 independent reflections
Radiation source: fine-focus sealed tube	3716 reflections with I > 2σ(I)
graphite	Rint = 0.049
φ and ω scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −25→24
Tmin = 0.978, Tmax = 0.985	k = −8→8
21978 measured reflections	l = −26→26

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.198	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.119P)2] where P = (Fo2 + 2Fc2)/3
6028 reflections	(Δ/σ)max = 0.001
363 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.36 e Å−3

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
O2A	0.77282 (7)	0.9079 (2)	0.18291 (7)	0.0240 (4)
O3A	0.85666 (7)	1.0679 (3)	0.38985 (7)	0.0302 (4)
O4A	1.01152 (7)	1.0476 (3)	0.22791 (7)	0.0298 (4)
O5A	0.97036 (7)	1.1039 (2)	0.41380 (7)	0.0266 (4)
O6A	1.04784 (7)	1.0940 (2)	0.33323 (7)	0.0250 (4)
C1A	0.74943 (10)	0.9542 (4)	0.28658 (10)	0.0246 (5)
H1AA	0.7543	0.9805	0.3315	0.030*
C2A	0.80226 (10)	0.9507 (3)	0.24675 (9)	0.0226 (5)
C3A	0.70337 (10)	0.8848 (3)	0.18383 (10)	0.0241 (5)
C4A	0.68697 (10)	0.9107 (4)	0.24655 (11)	0.0264 (5)
H4AA	0.6428	0.9012	0.2600	0.032*
C5A	0.87528 (10)	0.9763 (3)	0.25215 (9)	0.0223 (5)
H5AA	0.8931	0.9559	0.2125	0.027*
C6A	0.91304 (10)	1.0628 (3)	0.37011 (10)	0.0234 (5)
C7A	0.92562 (10)	1.0240 (3)	0.30207 (9)	0.0227 (5)
C8A	0.99672 (10)	1.0523 (4)	0.28365 (10)	0.0244 (5)
C9A	1.03783 (10)	1.0380 (3)	0.39939 (9)	0.0225 (5)
C10A	1.16592 (10)	1.0837 (4)	0.43581 (10)	0.0294 (5)
H10A	1.1762	1.1199	0.3922	0.035*
H10B	1.1991	1.1501	0.4677	0.035*
C11A	1.17412 (10)	0.8647 (4)	0.44459 (10)	0.0295 (5)
H11A	1.1698	0.8308	0.4899	0.035*
H11B	1.2203	0.8263	0.4355	0.035*
C12A	1.11918 (10)	0.7519 (4)	0.39880 (10)	0.0265 (5)
H12C	1.1237	0.6130	0.4082	0.032*
H12D	1.1273	0.7724	0.3534	0.032*
C13A	1.04505 (10)	0.8192 (4)	0.40769 (10)	0.0252 (5)
H13A	1.0117	0.7541	0.3755	0.030*
H13B	1.0346	0.7824	0.4512	0.030*
C14A	1.09154 (10)	1.1511 (4)	0.44459 (10)	0.0275 (5)
H14C	1.0834	1.1312	0.4899	0.033*
H14D	1.0868	1.2899	0.4349	0.033*
C15A	0.66067 (11)	0.8365 (4)	0.12100 (11)	0.0323 (5)
H15A	0.6659	0.9375	0.0893	0.049*
H15B	0.6125	0.8269	0.1280	0.049*
H15C	0.6758	0.7137	0.1049	0.049*
O2B	0.72619 (7)	0.4699 (2)	0.32748 (7)	0.0260 (4)
O3B	0.65167 (7)	0.3142 (3)	0.11772 (7)	0.0311 (4)
O4B	0.48850 (7)	0.3305 (3)	0.27231 (7)	0.0312 (4)
O5B	0.53852 (7)	0.2773 (3)	0.08899 (7)	0.0289 (4)
O6B	0.45715 (7)	0.2830 (3)	0.16647 (7)	0.0269 (4)
C1B	0.81544 (10)	0.4690 (4)	0.26779 (11)	0.0289 (5)
H1BA	0.8604	0.4789	0.2562	0.035*
C2B	0.75465 (10)	0.4255 (4)	0.22541 (11)	0.0262 (5)
H2BA	0.7519	0.3999	0.1805	0.031*
C3B	0.79632 (10)	0.4941 (4)	0.32922 (11)	0.0269 (5)
C4B	0.69981 (10)	0.4275 (3)	0.26259 (10)	0.0242 (5)
C5B	0.62670 (10)	0.4016 (3)	0.25433 (10)	0.0229 (5)
H5BA	0.6071	0.4197	0.2932	0.027*
C6B	0.50626 (10)	0.3260 (4)	0.21756 (10)	0.0255 (5)
C7B	0.57830 (10)	0.3558 (3)	0.20207 (10)	0.0238 (5)
C8B	0.59395 (10)	0.3186 (4)	0.13503 (10)	0.0249 (5)
C9B	0.46957 (10)	0.3378 (4)	0.10066 (10)	0.0251 (5)
C10B	0.34343 (11)	0.2776 (4)	0.06026 (11)	0.0326 (6)
H10C	0.3122	0.2052	0.0282	0.039*
H10D	0.3319	0.2447	0.1037	0.039*
C11B	0.41892 (11)	0.2164 (4)	0.05488 (11)	0.0309 (5)
H11C	0.4249	0.0789	0.0661	0.037*
H11D	0.4288	0.2335	0.0099	0.037*
C12B	0.45988 (10)	0.5554 (4)	0.09071 (10)	0.0263 (5)
H12A	0.4725	0.5916	0.0479	0.032*
H12B	0.4905	0.6249	0.1240	0.032*
C13B	0.38411 (10)	0.6153 (4)	0.09512 (10)	0.0285 (5)
H13C	0.3738	0.5974	0.1399	0.034*
H13D	0.3783	0.7530	0.0842	0.034*
C14B	0.33275 (11)	0.4947 (4)	0.04849 (10)	0.0331 (6)
H14A	0.2854	0.5296	0.0550	0.040*
H14B	0.3390	0.5252	0.0033	0.040*
C15B	0.83547 (11)	0.5452 (4)	0.39357 (12)	0.0354 (6)
H15D	0.8248	0.4525	0.4262	0.053*
H15E	0.8225	0.6742	0.4061	0.053*
H15F	0.8846	0.5421	0.3902	0.053*

	U11	U22	U33	U12	U13	U23
O2A	0.0205 (6)	0.0310 (10)	0.0199 (7)	−0.0014 (6)	−0.0002 (6)	−0.0009 (6)
O3A	0.0241 (7)	0.0446 (12)	0.0225 (7)	0.0018 (7)	0.0052 (6)	−0.0025 (7)
O4A	0.0222 (7)	0.0473 (12)	0.0202 (7)	−0.0007 (7)	0.0042 (6)	0.0054 (7)
O5A	0.0221 (7)	0.0372 (11)	0.0205 (7)	0.0017 (6)	0.0022 (6)	−0.0029 (6)
O6A	0.0209 (6)	0.0344 (10)	0.0191 (7)	−0.0023 (6)	0.0007 (6)	0.0042 (6)
C1A	0.0231 (9)	0.0292 (14)	0.0216 (10)	0.0022 (9)	0.0028 (8)	−0.0001 (8)
C2A	0.0232 (9)	0.0244 (13)	0.0195 (9)	0.0016 (8)	−0.0001 (8)	0.0003 (8)
C3A	0.0216 (9)	0.0237 (13)	0.0270 (10)	0.0008 (8)	0.0020 (9)	−0.0017 (8)
C4A	0.0215 (9)	0.0277 (14)	0.0304 (11)	0.0005 (9)	0.0039 (9)	0.0004 (9)
C5A	0.0250 (9)	0.0241 (13)	0.0178 (9)	0.0024 (8)	0.0030 (8)	0.0016 (8)
C6A	0.0215 (9)	0.0287 (14)	0.0195 (9)	0.0008 (8)	0.0003 (8)	−0.0006 (8)
C7A	0.0201 (9)	0.0290 (14)	0.0188 (9)	0.0032 (8)	0.0019 (8)	0.0027 (8)
C8A	0.0223 (9)	0.0298 (14)	0.0203 (10)	−0.0012 (9)	−0.0002 (8)	0.0053 (8)
C9A	0.0202 (9)	0.0284 (13)	0.0190 (9)	0.0002 (8)	0.0032 (8)	0.0018 (8)
C10A	0.0243 (10)	0.0415 (16)	0.0211 (10)	−0.0078 (9)	−0.0018 (9)	0.0002 (9)
C11A	0.0231 (9)	0.0432 (16)	0.0220 (10)	0.0022 (9)	0.0018 (9)	0.0016 (9)
C12A	0.0279 (10)	0.0283 (14)	0.0231 (10)	0.0012 (9)	0.0018 (9)	0.0022 (9)
C13A	0.0242 (9)	0.0326 (14)	0.0185 (9)	−0.0029 (9)	0.0019 (8)	0.0020 (8)
C14A	0.0258 (10)	0.0317 (15)	0.0242 (10)	−0.0063 (9)	−0.0002 (9)	−0.0022 (9)
C15A	0.0273 (10)	0.0378 (16)	0.0300 (11)	−0.0017 (10)	−0.0047 (9)	−0.0052 (10)
O2B	0.0213 (7)	0.0312 (10)	0.0250 (7)	−0.0001 (6)	0.0008 (6)	0.0000 (6)
O3B	0.0247 (7)	0.0426 (12)	0.0272 (8)	0.0018 (7)	0.0076 (6)	−0.0011 (7)
O4B	0.0226 (7)	0.0496 (12)	0.0216 (7)	0.0011 (7)	0.0039 (6)	0.0069 (7)
O5B	0.0224 (7)	0.0407 (11)	0.0238 (7)	0.0009 (7)	0.0031 (6)	−0.0016 (7)
O6B	0.0214 (7)	0.0393 (11)	0.0196 (7)	−0.0029 (6)	0.0010 (6)	0.0053 (6)
C1B	0.0222 (10)	0.0278 (14)	0.0367 (12)	0.0006 (9)	0.0044 (9)	0.0021 (10)
C2B	0.0236 (9)	0.0275 (14)	0.0278 (11)	0.0017 (9)	0.0046 (9)	0.0022 (9)
C3B	0.0220 (9)	0.0237 (13)	0.0341 (11)	0.0007 (8)	0.0001 (9)	0.0000 (9)
C4B	0.0247 (10)	0.0246 (13)	0.0230 (10)	0.0015 (8)	0.0014 (9)	0.0023 (8)
C5B	0.0237 (9)	0.0246 (13)	0.0212 (9)	0.0041 (8)	0.0062 (8)	0.0026 (8)
C6B	0.0231 (9)	0.0293 (14)	0.0234 (10)	0.0007 (9)	0.0002 (9)	0.0049 (9)
C7B	0.0210 (9)	0.0270 (13)	0.0236 (10)	0.0017 (8)	0.0035 (8)	0.0040 (8)
C8B	0.0220 (9)	0.0282 (14)	0.0245 (10)	0.0011 (8)	0.0031 (9)	0.0019 (9)
C9B	0.0215 (9)	0.0338 (14)	0.0199 (9)	−0.0026 (9)	0.0023 (8)	0.0009 (9)
C10B	0.0266 (10)	0.0460 (17)	0.0240 (10)	−0.0102 (10)	−0.0013 (9)	0.0016 (10)
C11B	0.0289 (10)	0.0371 (16)	0.0257 (10)	−0.0044 (10)	−0.0002 (9)	−0.0022 (10)
C12B	0.0265 (10)	0.0335 (14)	0.0191 (9)	−0.0038 (9)	0.0030 (9)	0.0020 (9)
C13B	0.0293 (10)	0.0317 (15)	0.0242 (10)	0.0022 (9)	0.0026 (9)	0.0049 (9)
C14B	0.0256 (10)	0.0517 (18)	0.0209 (10)	−0.0012 (10)	−0.0013 (9)	0.0070 (10)
C15B	0.0294 (11)	0.0390 (17)	0.0352 (12)	−0.0029 (10)	−0.0059 (10)	−0.0007 (11)

O2A—C3A	1.353 (2)	O2B—C3B	1.361 (2)
O2A—C2A	1.391 (2)	O2B—C4B	1.393 (2)
O3A—C6A	1.207 (2)	O3B—C8B	1.211 (2)
O4A—C8A	1.210 (2)	O4B—C6B	1.212 (2)
O5A—C6A	1.364 (2)	O5B—C8B	1.366 (2)
O5A—C9A	1.443 (2)	O5B—C9B	1.442 (2)
O6A—C8A	1.357 (2)	O6B—C6B	1.355 (2)
O6A—C9A	1.443 (2)	O6B—C9B	1.446 (2)
C1A—C2A	1.382 (3)	C1B—C3B	1.364 (3)
C1A—C4A	1.404 (3)	C1B—C2B	1.403 (3)
C1A—H1AA	0.9300	C1B—H1BA	0.9300
C2A—C5A	1.412 (3)	C2B—C4B	1.378 (3)
C3A—C4A	1.371 (3)	C2B—H2BA	0.9300
C3A—C15A	1.478 (3)	C3B—C15B	1.478 (3)
C4A—H4AA	0.9300	C4B—C5B	1.412 (3)
C5A—C7A	1.361 (3)	C5B—C7B	1.368 (3)
C5A—H5AA	0.9300	C5B—H5BA	0.9300
C6A—C7A	1.467 (3)	C6B—C7B	1.478 (3)
C7A—C8A	1.481 (3)	C7B—C8B	1.463 (3)
C9A—C13A	1.508 (3)	C9B—C12B	1.508 (3)
C9A—C14A	1.514 (3)	C9B—C11B	1.516 (3)
C10A—C11A	1.512 (4)	C10B—C14B	1.512 (4)
C10A—C14A	1.540 (3)	C10B—C11B	1.534 (3)
C10A—H10A	0.9700	C10B—H10C	0.9700
C10A—H10B	0.9700	C10B—H10D	0.9700
C11A—C12A	1.534 (3)	C11B—H11C	0.9700
C11A—H11A	0.9700	C11B—H11D	0.9700
C11A—H11B	0.9700	C12B—C13B	1.533 (3)
C12A—C13A	1.536 (3)	C12B—H12A	0.9700
C12A—H12C	0.9700	C12B—H12B	0.9700
C12A—H12D	0.9700	C13B—C14B	1.530 (3)
C13A—H13A	0.9700	C13B—H13C	0.9700
C13A—H13B	0.9700	C13B—H13D	0.9700
C14A—H14C	0.9700	C14B—H14A	0.9700
C14A—H14D	0.9700	C14B—H14B	0.9700
C15A—H15A	0.9600	C15B—H15D	0.9600
C15A—H15B	0.9600	C15B—H15E	0.9600
C15A—H15C	0.9600	C15B—H15F	0.9600
C3A—O2A—C2A	107.65 (15)	C3B—O2B—C4B	107.26 (16)
C6A—O5A—C9A	118.84 (15)	C8B—O5B—C9B	119.22 (16)
C8A—O6A—C9A	118.53 (15)	C6B—O6B—C9B	118.84 (15)
C2A—C1A—C4A	107.20 (18)	C3B—C1B—C2B	107.22 (18)
C2A—C1A—H1AA	126.4	C3B—C1B—H1BA	126.4
C4A—C1A—H1AA	126.4	C2B—C1B—H1BA	126.4
C1A—C2A—O2A	108.14 (16)	C4B—C2B—C1B	107.33 (19)
C1A—C2A—C5A	138.96 (19)	C4B—C2B—H2BA	126.3
O2A—C2A—C5A	112.90 (16)	C1B—C2B—H2BA	126.3
O2A—C3A—C4A	109.96 (18)	O2B—C3B—C1B	109.97 (19)
O2A—C3A—C15A	117.54 (17)	O2B—C3B—C15B	116.81 (18)
C4A—C3A—C15A	132.49 (18)	C1B—C3B—C15B	133.19 (19)
C3A—C4A—C1A	107.04 (18)	C2B—C4B—O2B	108.21 (17)
C3A—C4A—H4AA	126.5	C2B—C4B—C5B	139.2 (2)
C1A—C4A—H4AA	126.5	O2B—C4B—C5B	112.55 (17)
C7A—C5A—C2A	134.69 (18)	C7B—C5B—C4B	134.40 (18)
C7A—C5A—H5AA	112.7	C7B—C5B—H5BA	112.8
C2A—C5A—H5AA	112.7	C4B—C5B—H5BA	112.8
O3A—C6A—O5A	117.86 (18)	O4B—C6B—O6B	117.93 (17)
O3A—C6A—C7A	125.73 (18)	O4B—C6B—C7B	125.12 (19)
O5A—C6A—C7A	116.36 (16)	O6B—C6B—C7B	116.91 (17)
C5A—C7A—C6A	124.74 (17)	C5B—C7B—C8B	124.97 (17)
C5A—C7A—C8A	116.08 (18)	C5B—C7B—C6B	115.77 (18)
C6A—C7A—C8A	119.01 (18)	C8B—C7B—C6B	119.03 (18)
O4A—C8A—O6A	118.46 (17)	O3B—C8B—O5B	117.70 (18)
O4A—C8A—C7A	124.77 (19)	O3B—C8B—C7B	125.61 (19)
O6A—C8A—C7A	116.72 (17)	O5B—C8B—C7B	116.63 (16)
O5A—C9A—O6A	109.72 (16)	O5B—C9B—O6B	110.01 (16)
O5A—C9A—C13A	111.06 (16)	O5B—C9B—C12B	111.21 (17)
O6A—C9A—C13A	110.32 (17)	O6B—C9B—C12B	110.41 (17)
O5A—C9A—C14A	106.51 (17)	O5B—C9B—C11B	106.25 (17)
O6A—C9A—C14A	106.11 (16)	O6B—C9B—C11B	105.43 (17)
C13A—C9A—C14A	112.94 (18)	C12B—C9B—C11B	113.30 (18)
C11A—C10A—C14A	111.55 (18)	C14B—C10B—C11B	111.61 (19)
C11A—C10A—H10A	109.3	C14B—C10B—H10C	109.3
C14A—C10A—H10A	109.3	C11B—C10B—H10C	109.3
C11A—C10A—H10B	109.3	C14B—C10B—H10D	109.3
C14A—C10A—H10B	109.3	C11B—C10B—H10D	109.3
H10A—C10A—H10B	108.0	H10C—C10B—H10D	108.0
C10A—C11A—C12A	111.68 (18)	C9B—C11B—C10B	110.70 (19)
C10A—C11A—H11A	109.3	C9B—C11B—H11C	109.5
C12A—C11A—H11A	109.3	C10B—C11B—H11C	109.5
C10A—C11A—H11B	109.3	C9B—C11B—H11D	109.5
C12A—C11A—H11B	109.3	C10B—C11B—H11D	109.5
H11A—C11A—H11B	107.9	H11C—C11B—H11D	108.1
C11A—C12A—C13A	111.25 (18)	C9B—C12B—C13B	111.01 (18)
C11A—C12A—H12C	109.4	C9B—C12B—H12A	109.4
C13A—C12A—H12C	109.4	C13B—C12B—H12A	109.4
C11A—C12A—H12D	109.4	C9B—C12B—H12B	109.4
C13A—C12A—H12D	109.4	C13B—C12B—H12B	109.4
H12C—C12A—H12D	108.0	H12A—C12B—H12B	108.0
C9A—C13A—C12A	110.95 (17)	C14B—C13B—C12B	111.74 (19)
C9A—C13A—H13A	109.4	C14B—C13B—H13C	109.3
C12A—C13A—H13A	109.4	C12B—C13B—H13C	109.3
C9A—C13A—H13B	109.4	C14B—C13B—H13D	109.3
C12A—C13A—H13B	109.4	C12B—C13B—H13D	109.3
H13A—C13A—H13B	108.0	H13C—C13B—H13D	107.9
C9A—C14A—C10A	110.81 (18)	C10B—C14B—C13B	111.28 (18)
C9A—C14A—H14C	109.5	C10B—C14B—H14A	109.4
C10A—C14A—H14C	109.5	C13B—C14B—H14A	109.4
C9A—C14A—H14D	109.5	C10B—C14B—H14B	109.4
C10A—C14A—H14D	109.5	C13B—C14B—H14B	109.4
H14C—C14A—H14D	108.1	H14A—C14B—H14B	108.0
C3A—C15A—H15A	109.5	C3B—C15B—H15D	109.5
C3A—C15A—H15B	109.5	C3B—C15B—H15E	109.5
H15A—C15A—H15B	109.5	H15D—C15B—H15E	109.5
C3A—C15A—H15C	109.5	C3B—C15B—H15F	109.5
H15A—C15A—H15C	109.5	H15D—C15B—H15F	109.5
H15B—C15A—H15C	109.5	H15E—C15B—H15F	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C1A—H1AA···O3A	0.93	2.26	2.878 (3)	123
C4A—H4AA···O4Bi	0.93	2.59	3.408 (3)	147
C1B—H1BA···O4Aii	0.93	2.50	3.376 (3)	157
C2B—H2BA···O3B	0.93	2.26	2.884 (3)	124
C12B—H12B···O4Bi	0.97	2.53	3.420 (3)	152
C13A—H13A···O4Aii	0.97	2.54	3.405 (3)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4A—H4AA⋯O4Bi	0.93	2.59	3.408 (3)	147
C1B—H1BA⋯O4Aii	0.93	2.50	3.376 (3)	157
C12B—H12B⋯O4Bi	0.97	2.53	3.420 (3)	152
C13A—H13A⋯O4Aii	0.97	2.54	3.405 (3)	149

Symmetry codes: (i) ; (ii) .