Solvent-guest control of two extremely similar tetrahydrofuran inclusion structures

Racemic 2,4,6,8-tetracarbomethoxybicyclo[3.3.0]octa-2,6-diene-3,7-diol, C₁₆H₁₈O₁₀ (1), was known previously to yield two solvent-free polymorphs and also a clathrate inclusion crystal form. Crystallization of (1) yields two inclusion compounds containing tetrahydrofuran (THF): (1)₄·THF is obtained from a mixture of THF and methanol, whereas (1)₂·THF is obtained from pure THF. The X-ray crystal structures reveal that the two compounds are extremely similar and that their host arrangements are essentially identical. They differ, however, in the proportion, orientation and host-guest interaction of the included THF molecules. The disordered guest molecules in (1)₄·THF are oriented along the guest channel direction, whereas in (1)₂·THF they lie across the channel. This unusual solvent-guest control of inclusion structures has implications relating to the formation of polymorphic structures and other competing crystal forms.

Computing details

For both compounds, data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2013.

Figures

(1_0.25THF)

Crystal data

C16H18O10·0.25(C4H8O)	F(000) = 816
Mr = 388.33	Dx = 1.287 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.2247 (4) Å	Cell parameters from 5806 reflections
b = 8.3660 (3) Å	θ = 2.8–29.2°
c = 21.5073 (8) Å	µ = 0.11 mm^−1
β = 97.265 (2)°	T = 150 K
V = 2003.45 (13) Å^3	Plate, colourless
Z = 4	0.22 × 0.19 × 0.11 mm

Data collection

Bruker Kappa APEXII CCD diffractometer	3504 independent reflections
Radiation source: fine-focus sealed tube	2766 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
φ and ω scans with κ offsets	θmax = 25.0°, θmin = 3.1°
Absorption correction: multi-scan SADABS (Bruker, 2001)	h = −13→13
Tmin = 0.977, Tmax = 0.989	k = −8→9
13553 measured reflections	l = −25→25

Refinement

Refinement on F^2	48 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.074	H-atom parameters constrained
wR(F^2) = 0.254	w = 1/[σ^2(Fo^2) + (0.1529P)^2 + 2.1513P] where P = (Fo^2 + 2Fc^2)/3
S = 1.12	(Δ/σ)max < 0.001
3504 reflections	Δρmax = 1.10 e Å^−3
286 parameters	Δρmin = −0.35 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1T	0.5614 (15)	0.2759 (14)	0.5321 (9)	0.102 (4)	0.25
C1T	0.6376 (18)	0.176 (2)	0.5734 (12)	0.098 (4)	0.25
H1T1	0.6435	0.2160	0.6170	0.117*	0.25
H1T2	0.7193	0.1715	0.5606	0.117*	0.25
C2T	0.581 (2)	0.0166 (18)	0.5685 (13)	0.098 (4)	0.25
H2T1	0.6426	−0.0660	0.5640	0.117*	0.25
H2T2	0.5445	−0.0068	0.6070	0.117*	0.25
C3T	0.489 (2)	0.0132 (19)	0.5142 (12)	0.098 (4)	0.25
H3T1	0.4100	−0.0156	0.5267	0.117*	0.25
H3T2	0.5100	−0.0650	0.4827	0.117*	0.25
C4T	0.487 (2)	0.176 (2)	0.4889 (10)	0.098 (4)	0.25
H4T1	0.5175	0.1757	0.4477	0.118*	0.25
H4T2	0.4036	0.2169	0.4830	0.118*	0.25
O1	0.7414 (2)	0.5556 (3)	0.58488 (12)	0.0441 (7)
H1O	0.6724	0.5299	0.5924	0.066*
O2	1.0678 (2)	0.8534 (3)	0.81933 (11)	0.0382 (7)
H2O	1.1384	0.8670	0.8113	0.057*
O3	0.5584 (2)	0.5778 (3)	0.65583 (13)	0.0448 (7)
O4	0.5840 (2)	0.7565 (3)	0.73530 (12)	0.0382 (6)
O5	0.8620 (3)	0.8838 (3)	0.51905 (12)	0.0467 (7)
O6	1.0040 (2)	0.6952 (3)	0.52837 (11)	0.0371 (6)
O7	1.2271 (2)	0.9247 (3)	0.73881 (12)	0.0378 (6)
O8	1.1518 (2)	0.9371 (3)	0.63660 (11)	0.0362 (6)
O9	0.8089 (3)	1.0855 (3)	0.81342 (13)	0.0458 (7)
O10	0.7757 (2)	0.8594 (3)	0.86293 (11)	0.0429 (7)
C1	0.8043 (3)	0.8754 (4)	0.70004 (15)	0.0281 (7)
H1	0.7577	0.9774	0.6989	0.034*
C2	0.7288 (3)	0.7443 (4)	0.66754 (15)	0.0305 (8)
C3	0.7826 (3)	0.6768 (4)	0.62243 (15)	0.0307 (8)
C4	0.9049 (3)	0.7425 (4)	0.61637 (15)	0.0286 (8)
H4	0.9677	0.6633	0.6331	0.034*
C5	0.9110 (3)	0.8914 (4)	0.66018 (15)	0.0270 (7)
H5	0.9039	0.9924	0.6351	0.032*
C6	1.0192 (3)	0.8965 (4)	0.70862 (15)	0.0285 (7)
C7	0.9913 (3)	0.8653 (4)	0.76614 (15)	0.0285 (8)
C8	0.8603 (3)	0.8367 (4)	0.76847 (15)	0.0276 (7)
H8	0.8463	0.7218	0.7782	0.033*
C9	0.6166 (3)	0.6844 (4)	0.68422 (16)	0.0337 (8)
C10	0.4767 (4)	0.6959 (6)	0.7582 (2)	0.0531 (11)
H10A	0.4081	0.7071	0.7254	0.080*
H10B	0.4614	0.7567	0.7953	0.080*
H10C	0.4879	0.5828	0.7693	0.080*
C11	0.9199 (3)	0.7840 (4)	0.54928 (16)	0.0324 (8)
C12	1.0303 (4)	0.7283 (5)	0.46529 (17)	0.0457 (10)
H12A	0.9552	0.7326	0.4367	0.069*
H12B	1.0817	0.6434	0.4519	0.069*
H12C	1.0719	0.8311	0.4647	0.069*
C13	1.1425 (3)	0.9193 (4)	0.69730 (16)	0.0297 (8)
C14	1.2722 (3)	0.9543 (5)	0.6200 (2)	0.0481 (10)
H14A	1.3137	1.0406	0.6449	0.072*
H14B	1.2680	0.9800	0.5753	0.072*
H14C	1.3163	0.8541	0.6287	0.072*
C15	0.8123 (3)	0.9426 (4)	0.81660 (15)	0.0297 (8)
C16	0.7309 (4)	0.9531 (7)	0.91192 (19)	0.0620 (14)
H16A	0.7917	1.0317	0.9283	0.093*
H16B	0.7136	0.8822	0.9459	0.093*
H16C	0.6573	1.0088	0.8946	0.093*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1T	0.073 (7)	0.070 (6)	0.162 (12)	−0.005 (5)	0.010 (7)	0.013 (7)
C1T	0.069 (7)	0.070 (7)	0.153 (12)	−0.005 (5)	0.011 (7)	0.013 (7)
C2T	0.068 (7)	0.071 (7)	0.152 (12)	−0.001 (6)	0.007 (7)	0.015 (7)
C3T	0.068 (7)	0.069 (7)	0.155 (12)	0.000 (5)	0.008 (7)	0.012 (7)
C4T	0.069 (7)	0.070 (7)	0.155 (12)	0.002 (5)	0.008 (7)	0.014 (7)
O1	0.0439 (15)	0.0430 (15)	0.0426 (15)	−0.0100 (12)	−0.0053 (12)	−0.0138 (12)
O2	0.0354 (13)	0.0438 (15)	0.0317 (13)	0.0077 (12)	−0.0094 (10)	−0.0073 (11)
O3	0.0363 (14)	0.0486 (16)	0.0468 (15)	−0.0151 (12)	−0.0046 (12)	−0.0037 (12)
O4	0.0291 (13)	0.0402 (14)	0.0457 (15)	−0.0002 (11)	0.0058 (11)	−0.0011 (12)
O5	0.0510 (16)	0.0544 (17)	0.0330 (14)	0.0114 (14)	−0.0010 (12)	0.0109 (13)
O6	0.0432 (14)	0.0397 (14)	0.0288 (12)	0.0004 (12)	0.0057 (10)	−0.0015 (11)
O7	0.0277 (13)	0.0381 (14)	0.0450 (14)	0.0010 (10)	−0.0054 (11)	−0.0112 (11)
O8	0.0298 (13)	0.0368 (14)	0.0416 (14)	−0.0030 (10)	0.0033 (10)	0.0058 (11)
O9	0.0548 (18)	0.0299 (15)	0.0549 (17)	−0.0001 (12)	0.0160 (13)	−0.0092 (12)
O10	0.0445 (15)	0.0535 (17)	0.0315 (13)	0.0061 (12)	0.0076 (11)	0.0069 (12)
C1	0.0288 (16)	0.0228 (16)	0.0312 (17)	0.0011 (13)	−0.0018 (13)	0.0008 (13)
C2	0.0287 (17)	0.0308 (18)	0.0298 (17)	−0.0006 (13)	−0.0043 (13)	0.0018 (14)
C3	0.0334 (18)	0.0281 (17)	0.0281 (16)	−0.0031 (14)	−0.0066 (14)	0.0014 (14)
C4	0.0306 (17)	0.0267 (17)	0.0267 (16)	0.0012 (13)	−0.0031 (13)	0.0013 (13)
C5	0.0285 (17)	0.0235 (16)	0.0280 (16)	−0.0003 (13)	0.0001 (13)	0.0017 (13)
C6	0.0288 (17)	0.0211 (16)	0.0339 (17)	0.0017 (13)	−0.0024 (13)	−0.0032 (13)
C7	0.0297 (17)	0.0239 (17)	0.0296 (17)	0.0052 (13)	−0.0053 (13)	−0.0053 (13)
C8	0.0320 (17)	0.0212 (16)	0.0282 (16)	−0.0002 (13)	−0.0018 (13)	0.0006 (13)
C9	0.0268 (17)	0.0359 (19)	0.0358 (18)	−0.0030 (15)	−0.0059 (14)	0.0026 (15)
C10	0.036 (2)	0.060 (3)	0.066 (3)	0.0005 (19)	0.0168 (19)	0.003 (2)
C11	0.0343 (18)	0.0334 (18)	0.0280 (17)	−0.0041 (15)	−0.0021 (14)	−0.0023 (15)
C12	0.056 (2)	0.052 (2)	0.0303 (19)	−0.0066 (19)	0.0104 (17)	−0.0028 (17)
C13	0.0303 (17)	0.0205 (16)	0.0371 (18)	0.0000 (13)	−0.0008 (15)	−0.0043 (13)
C14	0.034 (2)	0.056 (3)	0.055 (2)	−0.0021 (19)	0.0100 (18)	0.011 (2)
C15	0.0266 (17)	0.031 (2)	0.0300 (17)	−0.0011 (14)	−0.0017 (13)	−0.0020 (14)
C16	0.057 (3)	0.096 (4)	0.034 (2)	0.026 (3)	0.0134 (19)	0.002 (2)

Geometric parameters (Å, º)

O1T—C1T	1.425 (9)	C1—C2	1.504 (5)
O1T—C4T	1.438 (9)	C1—C8	1.559 (4)
C1T—C2T	1.473 (10)	C1—C5	1.564 (5)
C1T—H1T1	0.9900	C1—H1	1.0000
C1T—H1T2	0.9900	C2—C3	1.331 (5)
C2T—C3T	1.459 (10)	C2—C9	1.442 (5)
C2T—H2T1	0.9900	C3—C4	1.500 (5)
C2T—H2T2	0.9900	C4—C11	1.514 (5)
C3T—C4T	1.463 (10)	C4—C5	1.558 (5)
C3T—H3T1	0.9900	C4—H4	1.0000
C3T—H3T2	0.9900	C5—C6	1.498 (4)
C4T—H4T1	0.9900	C5—H5	1.0000
C4T—H4T2	0.9900	C6—C7	1.340 (5)
O1—C3	1.342 (4)	C6—C13	1.447 (5)
O1—H1O	0.8400	C7—C8	1.496 (5)
O2—C7	1.345 (4)	C8—C15	1.513 (5)
O2—H2O	0.8400	C8—H8	1.0000
O3—C9	1.222 (4)	C10—H10A	0.9800
O4—C9	1.344 (4)	C10—H10B	0.9800
O4—C10	1.449 (5)	C10—H10C	0.9800
O5—C11	1.198 (4)	C12—H12A	0.9800
O6—C11	1.324 (4)	C12—H12B	0.9800
O6—C12	1.451 (4)	C12—H12C	0.9800
O7—C13	1.219 (4)	C14—H14A	0.9800
O8—C13	1.331 (4)	C14—H14B	0.9800
O8—C14	1.447 (4)	C14—H14C	0.9800
O9—C15	1.198 (4)	C16—H16A	0.9800
O10—C15	1.322 (4)	C16—H16B	0.9800
O10—C16	1.453 (5)	C16—H16C	0.9800
C1T—O1T—C4T	108.3 (7)	C6—C5—H5	110.7
O1T—C1T—C2T	105.5 (8)	C4—C5—H5	110.7
O1T—C1T—H1T1	110.6	C1—C5—H5	110.7
C2T—C1T—H1T1	110.6	C7—C6—C13	121.4 (3)
O1T—C1T—H1T2	110.6	C7—C6—C5	111.9 (3)
C2T—C1T—H1T2	110.6	C13—C6—C5	126.5 (3)
H1T1—C1T—H1T2	108.8	C6—C7—O2	127.0 (3)
C3T—C2T—C1T	109.3 (9)	C6—C7—C8	114.1 (3)
C3T—C2T—H2T1	109.8	O2—C7—C8	118.9 (3)
C1T—C2T—H2T1	109.8	C7—C8—C15	111.4 (3)
C3T—C2T—H2T2	109.8	C7—C8—C1	102.4 (3)
C1T—C2T—H2T2	109.8	C15—C8—C1	112.8 (3)
H2T1—C2T—H2T2	108.3	C7—C8—H8	110.0
C2T—C3T—C4T	104.8 (9)	C15—C8—H8	110.0
C2T—C3T—H3T1	110.8	C1—C8—H8	110.0
C4T—C3T—H3T1	110.8	O3—C9—O4	123.5 (3)
C2T—C3T—H3T2	110.8	O3—C9—C2	123.9 (3)
C4T—C3T—H3T2	110.8	O4—C9—C2	112.6 (3)
H3T1—C3T—H3T2	108.9	O4—C10—H10A	109.5
O1T—C4T—C3T	108.7 (9)	O4—C10—H10B	109.5
O1T—C4T—H4T1	109.9	H10A—C10—H10B	109.5
C3T—C4T—H4T1	109.9	O4—C10—H10C	109.5
O1T—C4T—H4T2	109.9	H10A—C10—H10C	109.5
C3T—C4T—H4T2	109.9	H10B—C10—H10C	109.5
H4T1—C4T—H4T2	108.3	O5—C11—O6	124.6 (3)
C3—O1—H1O	109.5	O5—C11—C4	124.0 (3)
C7—O2—H2O	109.5	O6—C11—C4	111.4 (3)
C9—O4—C10	116.4 (3)	O6—C12—H12A	109.5
C11—O6—C12	116.7 (3)	O6—C12—H12B	109.5
C13—O8—C14	116.4 (3)	H12A—C12—H12B	109.5
C15—O10—C16	115.5 (3)	O6—C12—H12C	109.5
C2—C1—C8	115.0 (3)	H12A—C12—H12C	109.5
C2—C1—C5	103.5 (3)	H12B—C12—H12C	109.5
C8—C1—C5	106.9 (3)	O7—C13—O8	124.3 (3)
C2—C1—H1	110.4	O7—C13—C6	123.7 (3)
C8—C1—H1	110.4	O8—C13—C6	112.0 (3)
C5—C1—H1	110.4	O8—C14—H14A	109.5
C3—C2—C9	121.7 (3)	O8—C14—H14B	109.5
C3—C2—C1	111.5 (3)	H14A—C14—H14B	109.5
C9—C2—C1	126.6 (3)	O8—C14—H14C	109.5
C2—C3—O1	127.3 (3)	H14A—C14—H14C	109.5
C2—C3—C4	114.4 (3)	H14B—C14—H14C	109.5
O1—C3—C4	118.3 (3)	O9—C15—O10	123.9 (3)
C3—C4—C11	112.3 (3)	O9—C15—C8	123.9 (3)
C3—C4—C5	102.2 (3)	O10—C15—C8	112.3 (3)
C11—C4—C5	113.0 (3)	O10—C16—H16A	109.5
C3—C4—H4	109.7	O10—C16—H16B	109.5
C11—C4—H4	109.7	H16A—C16—H16B	109.5
C5—C4—H4	109.7	O10—C16—H16C	109.5
C6—C5—C4	114.4 (3)	H16A—C16—H16C	109.5
C6—C5—C1	103.4 (3)	H16B—C16—H16C	109.5
C4—C5—C1	106.6 (3)
C4T—O1T—C1T—C2T	−19 (3)	C6—C7—C8—C15	−127.2 (3)
O1T—C1T—C2T—C3T	13 (3)	O2—C7—C8—C15	54.7 (4)
C1T—C2T—C3T—C4T	−3 (3)	C6—C7—C8—C1	−6.3 (4)
C1T—O1T—C4T—C3T	17 (3)	O2—C7—C8—C1	175.5 (3)
C2T—C3T—C4T—O1T	−8 (3)	C2—C1—C8—C7	125.1 (3)
C8—C1—C2—C3	−109.3 (3)	C5—C1—C8—C7	10.9 (3)
C5—C1—C2—C3	6.9 (4)	C2—C1—C8—C15	−115.0 (3)
C8—C1—C2—C9	65.7 (4)	C5—C1—C8—C15	130.8 (3)
C5—C1—C2—C9	−178.1 (3)	C10—O4—C9—O3	3.1 (5)
C9—C2—C3—O1	3.8 (5)	C10—O4—C9—C2	−175.7 (3)
C1—C2—C3—O1	179.1 (3)	C3—C2—C9—O3	−5.9 (5)
C9—C2—C3—C4	−173.3 (3)	C1—C2—C9—O3	179.5 (3)
C1—C2—C3—C4	2.0 (4)	C3—C2—C9—O4	172.9 (3)
C2—C3—C4—C11	−131.3 (3)	C1—C2—C9—O4	−1.7 (5)
O1—C3—C4—C11	51.3 (4)	C12—O6—C11—O5	3.0 (5)
C2—C3—C4—C5	−9.9 (4)	C12—O6—C11—C4	−177.5 (3)
O1—C3—C4—C5	172.7 (3)	C3—C4—C11—O5	62.9 (4)
C3—C4—C5—C6	126.9 (3)	C5—C4—C11—O5	−52.1 (5)
C11—C4—C5—C6	−112.2 (3)	C3—C4—C11—O6	−116.6 (3)
C3—C4—C5—C1	13.3 (3)	C5—C4—C11—O6	128.4 (3)
C11—C4—C5—C1	134.2 (3)	C14—O8—C13—O7	3.9 (5)
C2—C1—C5—C6	−133.4 (3)	C14—O8—C13—C6	−177.6 (3)
C8—C1—C5—C6	−11.6 (3)	C7—C6—C13—O7	−6.2 (5)
C2—C1—C5—C4	−12.5 (3)	C5—C6—C13—O7	178.9 (3)
C8—C1—C5—C4	109.3 (3)	C7—C6—C13—O8	175.3 (3)
C4—C5—C6—C7	−107.3 (3)	C5—C6—C13—O8	0.4 (4)
C1—C5—C6—C7	8.1 (3)	C16—O10—C15—O9	−0.7 (5)
C4—C5—C6—C13	68.1 (4)	C16—O10—C15—C8	178.6 (3)
C1—C5—C6—C13	−176.5 (3)	C7—C8—C15—O9	63.8 (4)
C13—C6—C7—O2	1.1 (5)	C1—C8—C15—O9	−50.8 (4)
C5—C6—C7—O2	176.8 (3)	C7—C8—C15—O10	−115.5 (3)
C13—C6—C7—C8	−176.9 (3)	C1—C8—C15—O10	129.9 (3)
C5—C6—C7—C8	−1.2 (4)

(1_0.5THF)

Crystal data

C16H18O10·0.5(C4H8O)	F(000) = 856
Mr = 406.35	Dx = 1.291 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.4634 (8) Å	Cell parameters from 5213 reflections
b = 8.5336 (7) Å	θ = 2.4–26.2°
c = 21.6678 (16) Å	µ = 0.11 mm^−1
β = 99.580 (2)°	T = 150 K
V = 2090.1 (3) Å^3	Block, colourless
Z = 4	0.23 × 0.23 × 0.13 mm

Data collection

Bruker Kappa APEXII CCD diffractometer	3662 independent reflections
Radiation source: fine-focus sealed tube	2883 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
φ and ω scans with κ offsets	θmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan SADABS (Bruker, 2001)	h = −13→13
Tmin = 0.975, Tmax = 0.986	k = −10→10
14221 measured reflections	l = −25→25

Refinement

Refinement on F^2	55 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.099	H-atom parameters constrained
wR(F^2) = 0.353	w = 1/[σ^2(Fo^2) + (0.2P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.54	(Δ/σ)max = 0.002
3662 reflections	Δρmax = 1.44 e Å^−3
293 parameters	Δρmin = −0.42 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1T	0.4914 (10)	0.278 (2)	0.5131 (6)	0.085 (3)	0.25
O1T'	0.5378 (14)	0.3508 (14)	0.5423 (8)	0.079 (3)	0.25
C1T	0.4814 (8)	0.2245 (12)	0.5728 (5)	0.075 (2)	0.5
H1T1	0.3990	0.1916	0.5740	0.090*	0.5
H1T2	0.5022	0.3096	0.6038	0.090*	0.5
C2T	0.5618 (8)	0.0916 (13)	0.5883 (6)	0.080 (3)	0.5
H2T1	0.5357	−0.0029	0.5633	0.096*	0.5
H2T2	0.5751	0.0660	0.6335	0.096*	0.5
C3T	0.6647 (8)	0.1672 (14)	0.5687 (5)	0.077 (3)	0.5
H3T1	0.7214	0.0878	0.5583	0.092*	0.5
H3T2	0.7057	0.2360	0.6023	0.092*	0.5
C4T	0.6149 (8)	0.2607 (14)	0.5123 (5)	0.081 (3)	0.5
H4T1	0.6536	0.3646	0.5136	0.098*	0.5
H4T2	0.6279	0.2058	0.4737	0.098*	0.5
O1	0.7475 (3)	0.5634 (4)	0.58387 (14)	0.0588 (9)
H1O1	0.6815	0.5322	0.5911	0.088*
O2	1.0627 (2)	0.8651 (3)	0.82097 (11)	0.0399 (7)
H1O2	1.1324	0.8802	0.8151	0.060*
O3	0.8598 (3)	0.8898 (4)	0.51906 (13)	0.0569 (9)
O4	0.9957 (2)	0.6998 (4)	0.52994 (11)	0.0445 (8)
O5	0.5612 (3)	0.5909 (4)	0.65122 (14)	0.0590 (10)
O6	0.5863 (2)	0.7723 (4)	0.72789 (13)	0.0470 (8)
O7	0.8092 (3)	1.1003 (3)	0.80455 (14)	0.0516 (9)
O8	0.7838 (2)	0.8881 (3)	0.86066 (11)	0.0428 (8)
O9	1.2196 (2)	0.9377 (3)	0.74459 (12)	0.0412 (8)
O10	1.1447 (2)	0.9500 (3)	0.64122 (12)	0.0398 (7)
C1	0.9094 (3)	0.8980 (4)	0.65948 (15)	0.0303 (8)
H1	0.9027	0.9966	0.6342	0.036*
C2	0.9039 (3)	0.7520 (4)	0.61674 (15)	0.0337 (9)
H2	0.9671	0.6762	0.6346	0.040*
C3	0.7837 (3)	0.6835 (5)	0.62089 (16)	0.0378 (9)
C4	0.7304 (3)	0.7521 (5)	0.66411 (15)	0.0355 (9)
C5	0.8043 (3)	0.8836 (4)	0.69728 (15)	0.0316 (9)
H5	0.7577	0.9831	0.6943	0.038*
C6	0.8579 (3)	0.8491 (4)	0.76617 (15)	0.0301 (8)
H6	0.8423	0.7381	0.7772	0.036*
C7	0.9890 (3)	0.8751 (4)	0.76644 (15)	0.0292 (8)
C8	1.0152 (3)	0.9033 (4)	0.71048 (16)	0.0303 (8)
C9	0.9154 (3)	0.7892 (5)	0.55010 (16)	0.0372 (9)
C10	1.0189 (4)	0.7334 (6)	0.46646 (17)	0.0532 (12)
H10A	0.9438	0.7378	0.4373	0.080*
H10B	1.0687	0.6504	0.4534	0.080*
H10C	1.0597	0.8343	0.4664	0.080*
C11	0.6192 (3)	0.6957 (5)	0.67945 (18)	0.0441 (10)
C12	0.4813 (4)	0.7169 (7)	0.7486 (3)	0.0672 (14)
H12A	0.4150	0.7198	0.7136	0.101*
H12B	0.4634	0.7840	0.7825	0.101*
H12C	0.4936	0.6090	0.7638	0.101*
C13	0.8146 (3)	0.9611 (5)	0.81139 (16)	0.0339 (9)
C14	0.7464 (4)	0.9900 (7)	0.9071 (2)	0.0613 (14)
H14A	0.7969	1.0834	0.9124	0.092*
H14B	0.7531	0.9342	0.9470	0.092*
H14C	0.6640	1.0215	0.8932	0.092*
C15	1.1361 (3)	0.9312 (4)	0.70168 (16)	0.0321 (9)
C16	1.2615 (3)	0.9763 (6)	0.6266 (2)	0.0539 (12)
H16A	1.3021	1.0562	0.6548	0.081*
H16B	1.2549	1.0123	0.5832	0.081*
H16C	1.3066	0.8784	0.6318	0.081*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1T	0.079 (6)	0.092 (7)	0.080 (6)	0.039 (5)	−0.002 (5)	0.029 (6)
O1T'	0.083 (6)	0.078 (7)	0.080 (6)	0.024 (5)	0.029 (5)	0.037 (5)
C1T	0.059 (4)	0.095 (6)	0.081 (5)	0.025 (4)	0.043 (4)	0.026 (5)
C2T	0.080 (5)	0.083 (6)	0.079 (5)	0.022 (5)	0.019 (5)	0.033 (5)
C3T	0.048 (4)	0.071 (6)	0.103 (6)	0.013 (4)	−0.014 (4)	0.032 (5)
C4T	0.073 (5)	0.091 (6)	0.088 (5)	0.006 (5)	0.041 (4)	0.048 (5)
O1	0.068 (2)	0.049 (2)	0.0537 (18)	−0.0130 (16)	−0.0080 (15)	−0.0153 (15)
O2	0.0367 (13)	0.0484 (18)	0.0304 (13)	0.0064 (12)	−0.0068 (10)	−0.0051 (12)
O3	0.0660 (19)	0.064 (2)	0.0373 (16)	0.0230 (17)	−0.0007 (13)	0.0136 (15)
O4	0.0542 (16)	0.0467 (18)	0.0328 (14)	0.0019 (14)	0.0079 (11)	−0.0040 (12)
O5	0.0472 (17)	0.069 (2)	0.0545 (18)	−0.0252 (16)	−0.0099 (13)	−0.0036 (16)
O6	0.0385 (15)	0.0523 (19)	0.0500 (16)	−0.0035 (13)	0.0064 (12)	0.0018 (14)
O7	0.072 (2)	0.0295 (17)	0.0589 (19)	0.0016 (14)	0.0263 (16)	−0.0050 (13)
O8	0.0476 (15)	0.0503 (19)	0.0306 (14)	0.0002 (13)	0.0073 (11)	0.0062 (12)
O9	0.0345 (14)	0.0402 (17)	0.0453 (16)	0.0005 (12)	−0.0033 (11)	−0.0110 (12)
O10	0.0356 (14)	0.0408 (17)	0.0419 (15)	−0.0023 (12)	0.0036 (11)	0.0063 (12)
C1	0.0344 (18)	0.0269 (19)	0.0274 (17)	0.0027 (15)	−0.0016 (13)	0.0025 (14)
C2	0.0384 (19)	0.030 (2)	0.0289 (17)	0.0031 (16)	−0.0054 (13)	−0.0024 (15)
C3	0.0425 (19)	0.032 (2)	0.0334 (18)	−0.0090 (18)	−0.0085 (15)	−0.0024 (16)
C4	0.0378 (19)	0.033 (2)	0.0314 (17)	−0.0039 (16)	−0.0055 (14)	0.0014 (15)
C5	0.0300 (17)	0.028 (2)	0.0345 (18)	0.0008 (15)	−0.0006 (13)	0.0026 (15)
C6	0.0333 (17)	0.0228 (18)	0.0332 (18)	−0.0001 (15)	0.0022 (13)	−0.0001 (15)
C7	0.0312 (17)	0.0227 (18)	0.0306 (17)	0.0066 (14)	−0.0037 (13)	−0.0061 (14)
C8	0.0323 (18)	0.0219 (17)	0.0337 (18)	0.0023 (15)	−0.0038 (13)	−0.0015 (14)
C9	0.0391 (19)	0.038 (2)	0.0316 (18)	−0.0032 (18)	−0.0031 (15)	−0.0061 (17)
C10	0.065 (3)	0.064 (3)	0.033 (2)	−0.005 (2)	0.0128 (18)	−0.006 (2)
C11	0.037 (2)	0.046 (3)	0.044 (2)	−0.0070 (19)	−0.0085 (16)	0.0093 (19)
C12	0.041 (2)	0.078 (4)	0.084 (3)	−0.007 (2)	0.017 (2)	0.019 (3)
C13	0.0331 (18)	0.033 (2)	0.0349 (19)	−0.0054 (16)	0.0036 (14)	−0.0039 (16)
C14	0.059 (3)	0.087 (4)	0.040 (2)	0.011 (3)	0.0160 (19)	−0.002 (2)
C15	0.0340 (18)	0.0240 (19)	0.0362 (18)	0.0032 (15)	−0.0002 (14)	−0.0042 (15)
C16	0.040 (2)	0.066 (3)	0.059 (3)	0.003 (2)	0.0157 (19)	0.014 (2)

Geometric parameters (Å, º)

O1T—C1T	1.395 (9)	O8—C14	1.448 (5)
O1T—C4T	1.427 (9)	O9—C15	1.220 (4)
O1T'—C4T	1.409 (9)	O10—C15	1.340 (4)
O1T'—C1T	1.470 (9)	O10—C16	1.443 (4)
C1T—C2T	1.465 (9)	C1—C8	1.500 (4)
C2T—C3T	1.467 (9)	C1—C2	1.548 (5)
C3T—C4T	1.492 (8)	C1—C5	1.570 (5)
O1—C3	1.325 (5)	C2—C9	1.505 (5)
O2—C7	1.336 (4)	C2—C3	1.513 (5)
O3—C9	1.206 (5)	C3—C4	1.336 (5)
O4—C9	1.324 (5)	C4—C11	1.452 (5)
O4—C10	1.472 (4)	C4—C5	1.514 (5)
O5—C11	1.217 (5)	C5—C6	1.545 (4)
O6—C11	1.342 (5)	C6—C13	1.511 (5)
O6—C12	1.433 (5)	C6—C7	1.519 (5)
O7—C13	1.197 (5)	C7—C8	1.319 (5)
O8—C13	1.333 (4)	C8—C15	1.450 (5)
C1T—O1T—C4T	102.3 (8)	C4—C5—C6	114.8 (3)
C4T—O1T'—C1T	99.4 (8)	C4—C5—C1	103.2 (3)
O1T—C1T—C2T	108.6 (9)	C6—C5—C1	107.6 (3)
O1T'—C1T—C2T	111.3 (8)	C13—C6—C7	109.7 (3)
C1T—C2T—C3T	95.7 (8)	C13—C6—C5	112.7 (3)
C2T—C3T—C4T	104.8 (7)	C7—C6—C5	102.1 (3)
O1T'—C4T—C3T	95.6 (9)	C8—C7—O2	128.2 (3)
O1T—C4T—C3T	106.9 (7)	C8—C7—C6	113.6 (3)
C9—O4—C10	116.1 (3)	O2—C7—C6	118.3 (3)
C11—O6—C12	116.4 (4)	C7—C8—C15	121.3 (3)
C13—O8—C14	115.1 (3)	C7—C8—C1	113.1 (3)
C15—O10—C16	117.1 (3)	C15—C8—C1	125.6 (3)
C8—C1—C2	114.3 (3)	O3—C9—O4	123.9 (3)
C8—C1—C5	102.4 (3)	O3—C9—C2	124.2 (3)
C2—C1—C5	106.9 (3)	O4—C9—C2	111.8 (3)
C9—C2—C3	111.4 (3)	O5—C11—O6	123.4 (4)
C9—C2—C1	113.8 (3)	O5—C11—C4	123.8 (4)
C3—C2—C1	102.8 (3)	O6—C11—C4	112.9 (4)
O1—C3—C4	129.0 (4)	O7—C13—O8	123.2 (3)
O1—C3—C2	117.4 (3)	O7—C13—C6	124.3 (3)
C4—C3—C2	113.6 (3)	O8—C13—C6	112.5 (3)
C3—C4—C11	122.5 (4)	O9—C15—O10	124.4 (3)
C3—C4—C5	111.9 (3)	O9—C15—C8	123.6 (3)
C11—C4—C5	125.5 (3)	O10—C15—C8	112.1 (3)