6-[Bis(ethoxycarbonyl)methyl]-6-deoxy-1,2;3,4-di-O-isopropyl-idene-d-galacto-pyran-ose.

The title compound, C(19)H(30)O(9), was prepared by substitution at the C6 position in 1,2;3,4-di-O-isopropyl-idene-6-O-trifluoro-methane-sulfonyl-d-galactose using sodium eth-oxy-malonate in dimethyl-formamide. The conformation is skew-boat (0)S(2), slightly distorted towards boat B(2,5). The inflexible pyran-ose structure makes the title compound a suitable inter-mediate for further synthetic work by keeping stereogenic carbon atoms safe from inversion. Several short intra-molecular C-H⋯ O contacts may stabilize the conformation of the mol-ecule. Inter-molecular C-H⋯O inter-actions also occur.

Related literature

For syntheses of this and similar compounds, see: Bouhlal et al. (2001 ▶); Doboszewski et al. (1987 ▶); Honeyman & Stening (1958 ▶); Sugihara et al. (1963 ▶); Tipson (1953 ▶); Cipolla et al. (1996 ▶). For the structures of diisopropyl­idene-galactopyran­ose and related compounds, see: Krajewski et al. (1990 ▶, 1994 ▶); Coutrot et al. (2001 ▶); Weaver et al. (2004 ▶, 2006 ▶); Boeyens et al. (1978 ▶); Berces et al. (2001 ▶). For conformations of small rings, see: Schwarz (1973 ▶); Cremer & Pople (1975 ▶); Boeyens (1978 ▶); Hill & Reilly (2007 ▶); Köll et al. (1994 ▶). For analysis of absolute structure, see: Flack (1983 ▶); Hooft et al. (2008 ▶).

Experimental

Crystal data

C19H30O9

M = 402.43

Orthorhombic,

a = 8.3287 (4) Å

b = 10.8895 (4) Å

c = 23.7706 (16) Å

V = 2155.9 (2) Å3

Z = 4

Cu Kα radiation

μ = 0.83 mm−1

T = 292 K

0.38 × 0.26 × 0.21 mm

Data collection

Rigaku R-AXIS RAPID II imaging plate diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi,1995 ▶) T min = 0.822, T max = 0.840

9353 measured reflections

3745 independent reflections

2824 reflections with I > 2σ(I)

R int = 0.075

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.096

S = 1.02

3745 reflections

275 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.15 e Å−3

Absolute structure: Flack (1983 ▶), 1607 Friedel pairs

Flack parameter: 0.06 (18)

Data collection: CrystalClear-SM Expert (Rigaku, 2009 ▶); cell refinement: HKL-2000 (Otwinowski & Minor, 1997 ▶); data reduction: CrystalClear-SM Expert; 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 ▶); software used to prepare material for publication: PLATON (Spek, 2009) ▶.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810046921/zl2327sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810046921/zl2327Isup2.hkl

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

C19H30O9	Dx = 1.240 Mg m−3
Mr = 402.43	Melting point: 322 K
Orthorhombic, P212121	Cu Kα radiation, λ = 1.54187 Å
Hall symbol: P 2ac 2ab	Cell parameters from 9579 reflections
a = 8.3287 (4) Å	θ = 6.7–68.2°
b = 10.8895 (4) Å	µ = 0.83 mm−1
c = 23.7706 (16) Å	T = 292 K
V = 2155.9 (2) Å3	Prism, colourless
Z = 4	0.38 × 0.26 × 0.21 mm
F(000) = 864

Rigaku R-AXIS RAPID II imaging plate diffractometer	3745 independent reflections
Radiation source: fine-focus sealed tube	2824 reflections with I > 2σ(I)
graphite	Rint = 0.075
Detector resolution: 10 pixels mm-1	θmax = 66.5°, θmin = 6.7°
ω scans	h = −6→9
Absorption correction: multi-scan (ABSCOR; Higashi,1995)	k = −12→10
Tmin = 0.822, Tmax = 0.840	l = −28→19
9353 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.040	w = 1/[σ2(Fo2) + (0.0285P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.096	(Δ/σ)max < 0.001
S = 1.02	Δρmax = 0.19 e Å−3
3745 reflections	Δρmin = −0.15 e Å−3
275 parameters	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.0057 (5)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1607 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.06 (18)

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	0.30842 (18)	0.05824 (11)	0.37716 (6)	0.0531 (4)
O2	0.2263 (2)	0.25329 (12)	0.35151 (6)	0.0653 (5)
O3	0.2044 (2)	0.30221 (12)	0.44385 (6)	0.0646 (5)
O4	0.0989 (2)	−0.00622 (15)	0.48415 (7)	0.0747 (5)
O5	0.3563 (2)	−0.07330 (14)	0.48515 (7)	0.0817 (6)
O6	0.6685 (2)	0.16820 (13)	0.27264 (7)	0.0718 (5)
O7	0.7237 (2)	0.22413 (15)	0.36113 (7)	0.0852 (6)
O8	0.7062 (2)	−0.17738 (13)	0.31233 (6)	0.0666 (5)
O9	0.8976 (2)	−0.03812 (18)	0.32008 (11)	0.1155 (9)
C1	0.1819 (3)	0.14252 (17)	0.37891 (9)	0.0523 (6)
H1A	0.088 (2)	0.1070 (8)	0.3597 (4)	0.063*
C2	0.1329 (3)	0.18443 (17)	0.43770 (9)	0.0573 (6)
H2A	0.012 (3)	0.1918 (2)	0.43999 (11)	0.069*
C3	0.1939 (3)	0.10213 (19)	0.48485 (10)	0.0600 (6)
H3A	0.1836 (4)	0.1456 (10)	0.5227 (8)	0.072*
C4	0.3665 (3)	0.0557 (2)	0.47632 (9)	0.0566 (6)
H4A	0.4367 (16)	0.0921 (8)	0.5044 (6)	0.068*
C5	0.4315 (3)	0.0817 (2)	0.41783 (9)	0.0490 (5)
H5A	0.4630 (7)	0.1708 (18)	0.41554 (10)	0.059*
C6	0.2124 (3)	0.35512 (18)	0.38911 (9)	0.0580 (6)
C7	0.3592 (3)	0.4335 (2)	0.38497 (12)	0.0860 (10)
H7A	0.3572 (11)	0.4945 (14)	0.4142 (7)	0.129*
H7B	0.3615 (12)	0.4733 (15)	0.3489 (6)	0.129*
H7C	0.4532 (15)	0.3831 (8)	0.3892 (8)	0.129*
C8	0.0607 (3)	0.4254 (2)	0.37542 (11)	0.0742 (8)
H8A	0.0457 (11)	0.4951 (13)	0.4040 (6)	0.111*
H8B	−0.0360 (13)	0.3671 (8)	0.3773 (7)	0.111*
H8C	0.0694 (9)	0.4617 (14)	0.3357 (6)	0.111*
C9	0.1971 (3)	−0.1063 (2)	0.49989 (10)	0.0657 (7)
C10	0.1486 (5)	−0.2177 (2)	0.46606 (14)	0.1124 (13)
H10A	0.034 (2)	−0.2405 (13)	0.4754 (7)	0.169*
H10B	0.222 (2)	−0.2886 (14)	0.4756 (8)	0.169*
H10C	0.157 (3)	−0.1985 (8)	0.4246 (7)	0.169*
C11	0.1883 (4)	−0.1306 (3)	0.56235 (11)	0.0901 (10)
H11A	0.0735 (17)	−0.1545 (17)	0.5730 (2)	0.135*
H11B	0.221 (2)	−0.0531 (13)	0.5838 (3)	0.135*
H11C	0.265 (2)	−0.2007 (15)	0.5725 (2)	0.135*
C12	0.5762 (3)	0.00309 (19)	0.40257 (9)	0.0557 (6)
H12A	0.5494 (4)	−0.0868 (13)	0.40954 (15)	0.067*
H12B	0.6699 (14)	0.0260 (3)	0.4279 (4)	0.067*
C13	0.6261 (3)	0.01977 (16)	0.34089 (9)	0.0510 (6)
H13A	0.535 (2)	0.0017 (4)	0.3179 (5)	0.061*
C14	0.6788 (3)	0.1493 (2)	0.32781 (11)	0.0585 (6)
C15	0.7163 (4)	0.2883 (2)	0.25156 (13)	0.0870 (10)
H15A	0.826 (2)	0.3111 (5)	0.2665 (3)	0.104*
H15B	0.6368 (15)	0.3532 (13)	0.2641 (3)	0.104*
C16	0.7196 (4)	0.2807 (2)	0.18966 (12)	0.0887 (10)
H16A	0.799 (2)	0.2184 (16)	0.1779 (2)	0.133*
H16B	0.750 (2)	0.3614 (13)	0.1739 (3)	0.133*
H16C	0.6122 (18)	0.2572 (17)	0.1757 (3)	0.133*
C17	0.7604 (3)	−0.0665 (2)	0.32388 (10)	0.0608 (6)
C18	0.8256 (3)	−0.2666 (2)	0.29360 (12)	0.0725 (8)
H18A	0.9058 (14)	−0.2830 (3)	0.3248 (5)	0.087*
H18B	0.8859 (11)	−0.2336 (6)	0.2598 (5)	0.087*
C19	0.7401 (4)	−0.3825 (2)	0.27835 (11)	0.0828 (10)
H19A	0.6860 (18)	−0.4159 (10)	0.3119 (5)	0.124*
H19B	0.8182 (11)	−0.4430 (10)	0.2641 (7)	0.124*
H19C	0.6597 (18)	−0.3651 (4)	0.2490 (6)	0.124*

	U11	U22	U33	U12	U13	U23
O1	0.0620 (10)	0.0461 (7)	0.0511 (9)	0.0023 (8)	−0.0101 (7)	−0.0076 (7)
O2	0.0976 (13)	0.0470 (8)	0.0515 (9)	0.0008 (8)	0.0044 (9)	0.0014 (6)
O3	0.0955 (13)	0.0472 (8)	0.0510 (9)	0.0018 (9)	−0.0093 (9)	−0.0041 (7)
O4	0.0744 (13)	0.0687 (10)	0.0811 (13)	−0.0030 (10)	0.0129 (9)	0.0232 (9)
O5	0.0809 (13)	0.0615 (9)	0.1028 (14)	0.0083 (10)	0.0273 (11)	0.0349 (9)
O6	0.0982 (15)	0.0526 (8)	0.0645 (11)	−0.0142 (9)	0.0074 (10)	0.0135 (8)
O7	0.1065 (16)	0.0676 (10)	0.0814 (13)	−0.0359 (11)	0.0086 (12)	−0.0092 (9)
O8	0.0630 (11)	0.0515 (8)	0.0854 (12)	−0.0037 (9)	0.0082 (10)	−0.0091 (8)
O9	0.0547 (12)	0.0826 (12)	0.209 (3)	−0.0130 (11)	0.0071 (14)	−0.0325 (14)
C1	0.0597 (15)	0.0464 (11)	0.0508 (13)	−0.0018 (12)	−0.0106 (12)	−0.0010 (9)
C2	0.0730 (18)	0.0486 (12)	0.0504 (14)	0.0037 (12)	0.0039 (12)	−0.0024 (10)
C3	0.0764 (18)	0.0570 (12)	0.0466 (14)	0.0017 (14)	0.0079 (13)	0.0032 (10)
C4	0.0679 (17)	0.0551 (12)	0.0467 (13)	−0.0024 (13)	−0.0017 (12)	0.0068 (11)
C5	0.0588 (15)	0.0430 (10)	0.0452 (13)	−0.0078 (11)	−0.0057 (11)	0.0016 (9)
C6	0.0759 (18)	0.0446 (11)	0.0534 (14)	0.0025 (13)	−0.0021 (13)	0.0002 (10)
C7	0.087 (2)	0.0612 (15)	0.110 (2)	−0.0130 (16)	−0.0115 (17)	0.0115 (15)
C8	0.0827 (19)	0.0598 (14)	0.0800 (19)	0.0081 (15)	−0.0057 (14)	0.0083 (13)
C9	0.0756 (19)	0.0581 (13)	0.0635 (16)	0.0010 (14)	0.0195 (15)	0.0125 (11)
C10	0.146 (4)	0.0824 (19)	0.108 (3)	−0.020 (2)	0.013 (2)	−0.0156 (18)
C11	0.109 (2)	0.0972 (19)	0.0644 (17)	0.015 (2)	0.0238 (17)	0.0259 (15)
C12	0.0600 (15)	0.0517 (11)	0.0555 (15)	−0.0035 (13)	−0.0012 (12)	0.0091 (10)
C13	0.0539 (14)	0.0458 (11)	0.0534 (14)	−0.0058 (11)	0.0009 (11)	0.0032 (10)
C14	0.0595 (17)	0.0515 (12)	0.0645 (16)	−0.0050 (12)	0.0059 (13)	0.0027 (11)
C15	0.113 (3)	0.0524 (13)	0.096 (2)	−0.0125 (16)	0.026 (2)	0.0189 (14)
C16	0.091 (2)	0.0784 (17)	0.096 (2)	0.0061 (17)	0.0249 (19)	0.0356 (16)
C17	0.0568 (17)	0.0571 (13)	0.0684 (16)	−0.0068 (13)	0.0037 (13)	−0.0003 (12)
C18	0.0680 (19)	0.0702 (15)	0.0794 (18)	0.0135 (16)	0.0072 (15)	−0.0077 (13)
C19	0.109 (3)	0.0585 (14)	0.0807 (19)	0.0077 (16)	−0.0041 (17)	−0.0091 (13)

O1—C1	1.398 (2)	C7—H7C	0.9614
O1—C5	1.432 (2)	C8—H8A	1.0264
O2—C1	1.420 (2)	C8—H8B	1.0264
O2—C6	1.429 (2)	C8—H8C	1.0264
O3—C2	1.422 (2)	C9—C11	1.510 (3)
O3—C6	1.425 (2)	C9—C10	1.511 (4)
O4—C9	1.413 (3)	C10—H10A	1.0094
O4—C3	1.421 (2)	C10—H10B	1.0094
O5—C9	1.418 (3)	C10—H10C	1.0094
O5—C4	1.423 (3)	C11—H11A	1.0229
O6—C14	1.330 (3)	C11—H11B	1.0229
O6—C15	1.456 (2)	C11—H11C	1.0229
O7—C14	1.196 (3)	C12—C13	1.535 (3)
O8—C17	1.317 (3)	C12—H12A	1.0171
O8—C18	1.460 (3)	C12—H12B	1.0171
O9—C17	1.187 (3)	C13—C14	1.509 (3)
C1—C2	1.526 (3)	C13—C17	1.515 (3)
C1—H1A	0.9878	C13—H13A	0.9571
C2—C3	1.523 (3)	C15—C16	1.474 (4)
C2—H2A	1.0091	C15—H15A	1.0130
C3—C4	1.537 (3)	C15—H15B	1.0130
C3—H3A	1.0200	C16—H16A	0.9879
C4—C5	1.518 (3)	C16—H16B	0.9879
C4—H4A	0.9713	C16—H16C	0.9879
C5—C12	1.522 (3)	C18—C19	1.494 (3)
C5—H5A	1.0065	C18—H18A	1.0133
C6—C7	1.494 (3)	C18—H18B	1.0133
C6—C8	1.513 (3)	C19—H19A	0.9857
C7—H7A	0.9614	C19—H19B	0.9857
C7—H7B	0.9614	C19—H19C	0.9857
C1—O1—C5	113.72 (15)	O4—C9—C10	108.9 (2)
C1—O2—C6	110.56 (16)	O5—C9—C10	108.8 (2)
C2—O3—C6	106.90 (15)	C11—C9—C10	111.7 (2)
C9—O4—C3	108.33 (17)	C9—C10—H10A	109.5
C9—O5—C4	110.03 (18)	C9—C10—H10B	109.5
C14—O6—C15	117.44 (19)	H10A—C10—H10B	109.5
C17—O8—C18	116.12 (19)	C9—C10—H10C	109.5
O1—C1—O2	110.33 (18)	H10A—C10—H10C	109.5
O1—C1—C2	115.16 (18)	H10B—C10—H10C	109.5
O2—C1—C2	103.64 (15)	C9—C11—H11A	109.5
O1—C1—H1A	109.2	C9—C11—H11B	109.5
O2—C1—H1A	109.2	H11A—C11—H11B	109.5
C2—C1—H1A	109.2	C9—C11—H11C	109.5
O3—C2—C3	108.38 (19)	H11A—C11—H11C	109.5
O3—C2—C1	104.60 (18)	H11B—C11—H11C	109.5
C3—C2—C1	114.14 (18)	C5—C12—C13	112.06 (17)
O3—C2—H2A	109.8	C5—C12—H12A	109.2
C3—C2—H2A	109.8	C13—C12—H12A	109.2
C1—C2—H2A	109.8	C5—C12—H12B	109.2
O4—C3—C2	107.09 (19)	C13—C12—H12B	109.2
O4—C3—C4	104.26 (18)	H12A—C12—H12B	107.9
C2—C3—C4	114.1 (2)	C14—C13—C17	108.06 (19)
O4—C3—H3A	110.4	C14—C13—C12	112.71 (17)
C2—C3—H3A	110.4	C17—C13—C12	112.42 (17)
C4—C3—H3A	110.4	C14—C13—H13A	107.8
O5—C4—C5	109.92 (18)	C17—C13—H13A	107.8
O5—C4—C3	104.44 (18)	C12—C13—H13A	107.8
C5—C4—C3	113.11 (19)	O7—C14—O6	124.5 (2)
O5—C4—H4A	109.7	O7—C14—C13	126.2 (2)
C5—C4—H4A	109.7	O6—C14—C13	109.2 (2)
C3—C4—H4A	109.7	O6—C15—C16	107.3 (2)
O1—C5—C4	109.26 (18)	O6—C15—H15A	110.2
O1—C5—C12	107.79 (17)	C16—C15—H15A	110.2
C4—C5—C12	113.28 (17)	O6—C15—H15B	110.2
O1—C5—H5A	108.8	C16—C15—H15B	110.2
C4—C5—H5A	108.8	H15A—C15—H15B	108.5
C12—C5—H5A	108.8	C15—C16—H16A	109.5
O3—C6—O2	105.14 (15)	C15—C16—H16B	109.5
O3—C6—C7	109.3 (2)	H16A—C16—H16B	109.5
O2—C6—C7	109.6 (2)	C15—C16—H16C	109.5
O3—C6—C8	111.2 (2)	H16A—C16—H16C	109.5
O2—C6—C8	109.00 (19)	H16B—C16—H16C	109.5
C7—C6—C8	112.36 (18)	O9—C17—O8	123.5 (2)
C6—C7—H7A	109.5	O9—C17—C13	124.7 (2)
C6—C7—H7B	109.5	O8—C17—C13	111.8 (2)
H7A—C7—H7B	109.5	O8—C18—C19	108.2 (2)
C6—C7—H7C	109.5	O8—C18—H18A	110.1
H7A—C7—H7C	109.5	C19—C18—H18A	110.1
H7B—C7—H7C	109.5	O8—C18—H18B	110.1
C6—C8—H8A	109.5	C19—C18—H18B	110.1
C6—C8—H8B	109.5	H18A—C18—H18B	108.4
H8A—C8—H8B	109.5	C18—C19—H19A	109.5
C6—C8—H8C	109.5	C18—C19—H19B	109.5
H8A—C8—H8C	109.5	H19A—C19—H19B	109.5
H8B—C8—H8C	109.5	C18—C19—H19C	109.5
O4—C9—O5	106.31 (17)	H19A—C19—H19C	109.5
O4—C9—C11	111.6 (2)	H19B—C19—H19C	109.5
O5—C9—C11	109.4 (2)
C5—O1—C1—O2	78.7 (2)	C2—O3—C6—C7	−146.7 (2)
C5—O1—C1—C2	−38.2 (2)	C2—O3—C6—C8	88.7 (2)
C6—O2—C1—O1	−122.13 (19)	C1—O2—C6—O3	16.5 (3)
C6—O2—C1—C2	1.7 (3)	C1—O2—C6—C7	133.8 (2)
C6—O3—C2—C3	152.18 (19)	C1—O2—C6—C8	−102.8 (2)
C6—O3—C2—C1	30.0 (2)	C3—O4—C9—O5	−26.3 (2)
O1—C1—C2—O3	101.3 (2)	C3—O4—C9—C11	93.0 (3)
O2—C1—C2—O3	−19.2 (2)	C3—O4—C9—C10	−143.3 (2)
O1—C1—C2—C3	−16.9 (3)	C4—O5—C9—O4	17.1 (3)
O2—C1—C2—C3	−137.5 (2)	C4—O5—C9—C11	−103.5 (2)
C9—O4—C3—C2	145.74 (19)	C4—O5—C9—C10	134.2 (2)
C9—O4—C3—C4	24.4 (2)	O1—C5—C12—C13	51.9 (2)
O3—C2—C3—O4	169.21 (18)	C4—C5—C12—C13	172.91 (19)
C1—C2—C3—O4	−74.7 (3)	C5—C12—C13—C14	62.8 (2)
O3—C2—C3—C4	−76.0 (2)	C5—C12—C13—C17	−174.81 (18)
C1—C2—C3—C4	40.2 (3)	C15—O6—C14—O7	0.4 (4)
C9—O5—C4—C5	−123.7 (2)	C15—O6—C14—C13	−179.3 (2)
C9—O5—C4—C3	−2.1 (3)	C17—C13—C14—O7	−104.0 (3)
O4—C3—C4—O5	−13.5 (2)	C12—C13—C14—O7	20.9 (4)
C2—C3—C4—O5	−129.97 (19)	C17—C13—C14—O6	75.7 (3)
O4—C3—C4—C5	106.0 (2)	C12—C13—C14—O6	−159.4 (2)
C2—C3—C4—C5	−10.5 (3)	C14—O6—C15—C16	171.0 (2)
C1—O1—C5—C4	69.3 (2)	C18—O8—C17—O9	−0.5 (4)
C1—O1—C5—C12	−167.25 (15)	C18—O8—C17—C13	177.98 (19)
O5—C4—C5—O1	74.9 (2)	C14—C13—C17—O9	23.8 (3)
C3—C4—C5—O1	−41.4 (2)	C12—C13—C17—O9	−101.2 (3)
O5—C4—C5—C12	−45.3 (3)	C14—C13—C17—O8	−154.6 (2)
C3—C4—C5—C12	−161.60 (18)	C12—C13—C17—O8	80.4 (2)
C2—O3—C6—O2	−29.2 (3)	C17—O8—C18—C19	−175.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O9i	0.98	2.43	3.381 (3)	163
C5—H5A···O7	1.01	2.59	3.185 (3)	117
C8—H8B···O7i	1.03	2.56	3.577 (3)	169
C12—H12A···O5	1.02	2.42	2.811 (3)	102
C13—H13A···O1	0.96	2.43	2.814 (3)	103
C16—H16B···O1ii	0.99	2.51	3.422 (3)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯O9i	0.98	2.43	3.381 (3)	163
C5—H5A⋯O7	1.01	2.59	3.185 (3)	117
C8—H8B⋯O7i	1.03	2.56	3.577 (3)	169
C12—H12A⋯O5	1.02	2.42	2.811 (3)	102
C13—H13A⋯O1	0.96	2.43	2.814 (3)	103
C16—H16B⋯O1ii	0.99	2.51	3.422 (3)	153

Symmetry codes: (i) ; (ii) .