Benzo-cis-cyclo­hexano-14-crown-4 and its lithium thio­cyanate complex

The structures of a 14-crown-4 ether containing both benzo and cyclo­hexano substituents, 2,6,13,17-tetraoxatricyclo-[16.4.0.0^7,12]docosa-1(18),19,21-triene, C₁₈H₂₆O₄, and its lith­ium complex, [2,6,13,17-tetraoxatricyclo[16.4.0.0^7,12]docosa-1(18),19,21-triene-κ⁴O](thio­cyanato-N)­lith­ium(I), [Li(NCS)-(C₁₈H₂₆O₄)], are presented. The conformation of the free crown, (I), is not preorganized for cation binding, as its donor dipoles are oriented towards opposite sides of the crown ring. The Li⁺-crown complex, (II), exhibits two formula units in the asymmetric unit. The binding conformation observed in (II) does not completely reorient the dipoles to one point, resulting in a long Li—O bond length [2.068 (5) and 2.073 (5) Å].

Computing details

Data collection: CAD-4-PC (Nonius, 1993) for (I); CAD-4-PC (Nonius, 1996) for (II). For both compounds, cell refinement: CAD-4-PC; data reduction: XCAD4 (Harms, 1995). Program(s) used to solve structure: SHELXS86 (Sheldrick, 1990) for (I); SHELXS97 (Sheldrick, 1990) for (II). For both compounds, program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

(I)

Crystal data

C18H26O4	F(000) = 664
Mr = 306.4	Dx = 1.26 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.9888 (11) Å	Cell parameters from 25 reflections
b = 15.5672 (9) Å	θ = 10.1–14.4°
c = 10.9050 (9) Å	µ = 0.09 mm^−1
β = 107.841 (7)°	T = 163 K
V = 1614.2 (2) Å^3	Prism, colourless
Z = 4	0.43 × 0.37 × 0.36 mm

Data collection

Nonius CAD4 diffractometer	Rint = 0.021
Radiation source: fine-focus sealed tube	θmax = 27.5°, θmin = 2.3°
Graphite monochromator	h = 0→12
ω–scans	k = −10→20
4433 measured reflections	l = −14→13
3677 independent reflections	3 standard reflections every 120 min
2935 reflections with I > 2σ(I)	intensity decay: none

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.100	H-atom parameters not refined
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0443P)^2 + 0.429P] where P = (Fo^2 + 2Fc^2)/3
3677 reflections	(Δ/σ)max < 0.001
199 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.24 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.

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.02977 (8)	0.50591 (5)	0.28511 (8)	0.02213 (19)
C2	0.16141 (12)	0.51025 (7)	0.26878 (11)	0.0185 (2)
C3	0.27383 (12)	0.46327 (7)	0.34711 (11)	0.0202 (2)
O4	0.25162 (10)	0.41149 (6)	0.44142 (9)	0.0268 (2)
C5	0.29291 (14)	0.32301 (8)	0.43957 (12)	0.0247 (3)
H5A	0.3815	0.3191	0.4171	0.030*
H5B	0.2192	0.2906	0.3745	0.030*
C6	0.31347 (13)	0.28578 (8)	0.57208 (12)	0.0249 (3)
H6A	0.3871	0.3191	0.6358	0.030*
H6B	0.3474	0.2259	0.5737	0.030*
C7	0.18109 (13)	0.28626 (8)	0.61168 (11)	0.0226 (3)
H7A	0.2023	0.2674	0.7023	0.027*
H7B	0.1410	0.3449	0.6038	0.027*
O8	0.08379 (8)	0.22881 (5)	0.52851 (8)	0.02079 (19)
C9	−0.04501 (12)	0.21903 (7)	0.55798 (11)	0.0183 (2)
H9	−0.0222	0.2016	0.6504	0.022*
C10	−0.13192 (12)	0.30154 (7)	0.53830 (11)	0.0184 (2)
H10	−0.0777	0.3469	0.5980	0.022*
O11	−0.15526 (9)	0.32837 (5)	0.40792 (8)	0.02013 (19)
C12	−0.18412 (13)	0.41780 (7)	0.38833 (12)	0.0222 (3)
H12A	−0.1084	0.4518	0.4486	0.027*
H12B	−0.2742	0.4319	0.4039	0.027*
C13	−0.19275 (12)	0.43860 (8)	0.25042 (12)	0.0228 (3)
H13A	−0.2595	0.3984	0.1922	0.027*
H13B	−0.2306	0.4974	0.2299	0.027*
C14	−0.05251 (12)	0.43289 (7)	0.22480 (11)	0.0202 (2)
H14A	−0.0038	0.3790	0.2611	0.024*
H14B	−0.0665	0.4335	0.1309	0.024*
C15	0.18308 (13)	0.56648 (7)	0.17765 (12)	0.0223 (3)
H15	0.1063	0.5986	0.1245	0.027*
C16	0.31557 (14)	0.57619 (8)	0.16336 (12)	0.0258 (3)
H16	0.3295	0.6144	0.1004	0.031*
C17	0.42707 (13)	0.52973 (8)	0.24170 (13)	0.0268 (3)
H17	0.5182	0.5362	0.2327	0.032*
C18	0.40699 (13)	0.47375 (8)	0.33333 (12)	0.0254 (3)
H18	0.4844	0.4423	0.3870	0.031*
C19	−0.12567 (12)	0.14622 (7)	0.47504 (12)	0.0208 (2)
H19A	−0.0685	0.0931	0.4942	0.025*
H19B	−0.1426	0.1604	0.3830	0.025*
C20	−0.26653 (13)	0.13050 (8)	0.49947 (13)	0.0247 (3)
H20A	−0.3200	0.0864	0.4386	0.030*
H20B	−0.2491	0.1082	0.5880	0.030*
C21	−0.35404 (13)	0.21249 (8)	0.48322 (12)	0.0238 (3)
H21A	−0.3830	0.2304	0.3917	0.029*
H21B	−0.4401	0.2011	0.5075	0.029*
C22	−0.27063 (13)	0.28478 (8)	0.56684 (12)	0.0216 (2)
H22A	−0.2505	0.2694	0.6588	0.026*
H22B	−0.3278	0.3379	0.5508	0.026*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0183 (4)	0.0187 (4)	0.0323 (5)	−0.0023 (3)	0.0121 (3)	−0.0061 (3)
C2	0.0184 (5)	0.0156 (5)	0.0234 (5)	−0.0016 (4)	0.0091 (4)	−0.0041 (4)
C3	0.0233 (6)	0.0179 (5)	0.0221 (6)	−0.0009 (4)	0.0109 (5)	0.0008 (4)
O4	0.0361 (5)	0.0209 (4)	0.0301 (5)	0.0082 (4)	0.0201 (4)	0.0086 (4)
C5	0.0279 (6)	0.0192 (6)	0.0315 (7)	0.0059 (5)	0.0157 (5)	0.0046 (5)
C6	0.0187 (6)	0.0250 (6)	0.0297 (6)	0.0012 (5)	0.0054 (5)	0.0075 (5)
C7	0.0225 (6)	0.0243 (6)	0.0206 (6)	−0.0037 (5)	0.0060 (5)	−0.0004 (5)
O8	0.0180 (4)	0.0225 (4)	0.0230 (4)	−0.0009 (3)	0.0081 (3)	−0.0035 (3)
C9	0.0189 (5)	0.0187 (5)	0.0189 (5)	0.0004 (4)	0.0080 (4)	0.0007 (4)
C10	0.0212 (6)	0.0168 (5)	0.0190 (5)	−0.0012 (4)	0.0086 (4)	−0.0024 (4)
O11	0.0269 (4)	0.0141 (4)	0.0211 (4)	0.0006 (3)	0.0098 (3)	0.0010 (3)
C12	0.0226 (6)	0.0146 (5)	0.0327 (6)	0.0026 (4)	0.0132 (5)	0.0027 (5)
C13	0.0172 (5)	0.0203 (6)	0.0303 (6)	0.0018 (4)	0.0064 (5)	0.0056 (5)
C14	0.0210 (6)	0.0166 (5)	0.0237 (6)	−0.0021 (4)	0.0078 (5)	−0.0018 (4)
C15	0.0256 (6)	0.0181 (5)	0.0234 (6)	0.0020 (5)	0.0075 (5)	0.0007 (4)
C16	0.0336 (7)	0.0205 (6)	0.0285 (6)	−0.0032 (5)	0.0170 (5)	0.0021 (5)
C17	0.0222 (6)	0.0272 (6)	0.0349 (7)	−0.0050 (5)	0.0145 (5)	−0.0012 (5)
C18	0.0184 (6)	0.0285 (6)	0.0287 (6)	0.0020 (5)	0.0060 (5)	0.0028 (5)
C19	0.0227 (6)	0.0154 (5)	0.0256 (6)	0.0016 (4)	0.0094 (5)	−0.0013 (4)
C20	0.0265 (6)	0.0183 (6)	0.0317 (6)	−0.0043 (5)	0.0124 (5)	−0.0033 (5)
C21	0.0194 (6)	0.0246 (6)	0.0293 (6)	−0.0017 (5)	0.0104 (5)	−0.0011 (5)
C22	0.0236 (6)	0.0200 (6)	0.0249 (6)	0.0014 (5)	0.0129 (5)	−0.0014 (5)

Geometric parameters (Å, º)

O1—C2	1.3815 (13)	C5—H5B	0.99
O1—C14	1.4384 (13)	C6—H6A	0.99
C2—C15	1.3902 (16)	C6—H6B	0.99
C2—C3	1.3920 (16)	C7—H7A	0.99
C3—O4	1.3772 (14)	C7—H7B	0.99
C3—C18	1.3932 (16)	C9—H9	1.00
O4—C5	1.4398 (14)	C10—H10	1.00
C5—C6	1.5114 (17)	C12—H12A	0.99
C6—C7	1.5116 (16)	C12—H12B	0.99
C7—O8	1.4237 (14)	C13—H13A	0.99
O8—C9	1.4266 (13)	C13—H13B	0.99
C9—C19	1.5183 (16)	C14—H14A	0.99
C9—C10	1.5282 (16)	C14—H14B	0.99
C10—O11	1.4308 (13)	C15—H15	0.95
C10—C22	1.5326 (15)	C16—H16	0.95
O11—C12	1.4244 (13)	C17—H17	0.95
C12—C13	1.5148 (17)	C18—H18	0.95
C13—C14	1.5127 (15)	C19—H19A	0.99
C15—C16	1.3874 (17)	C19—H19B	0.99
C16—C17	1.3822 (19)	C20—H20A	0.99
C17—C18	1.3860 (18)	C20—H20B	0.99
C19—C20	1.5298 (16)	C21—H21A	0.99
C20—C21	1.5262 (17)	C21—H21B	0.99
C21—C22	1.5254 (17)	C22—H22A	0.99
C5—H5A	0.99	C22—H22B	0.99
C2—O1—C14	114.38 (8)	C19—C9—H9	108
O1—C2—C15	119.06 (10)	O11—C10—H10	109
O1—C2—C3	121.06 (10)	C9—C10—H10	109
C15—C2—C3	119.77 (11)	C22—C10—H10	109
O4—C3—C2	118.78 (10)	O11—C12—H12A	110
O4—C3—C18	121.78 (11)	O11—C12—H12B	110
C2—C3—C18	119.32 (11)	C13—C12—H12A	110
C3—O4—C5	115.92 (9)	C13—C12—H12B	110
O4—C5—C6	108.00 (10)	H12A—C12—H12B	108
C5—C6—C7	113.37 (10)	C12—C13—H13A	109
O8—C7—C6	107.52 (10)	C12—C13—H13B	109
C7—O8—C9	114.22 (8)	C14—C13—H13A	109
O8—C9—C19	107.22 (9)	C14—C13—H13B	109
O8—C9—C10	113.04 (9)	H13A—C13—H13B	108
C19—C9—C10	111.64 (9)	O1—C14—H14A	110
O11—C10—C9	107.31 (9)	O1—C14—H14B	110
O11—C10—C22	111.68 (9)	C13—C14—H14A	110
C9—C10—C22	109.78 (9)	C13—C14—H14B	110
C12—O11—C10	113.47 (9)	H14A—C14—H14B	108
O11—C12—C13	107.78 (10)	C2—C15—H15	120
C14—C13—C12	113.36 (10)	C16—C15—H15	120
O1—C14—C13	107.51 (9)	C15—C16—H16	120
C16—C15—C2	120.78 (11)	C17—C16—H16	120
C17—C16—C15	119.29 (11)	C16—C17—H17	120
C16—C17—C18	120.50 (11)	C18—C17—H17	120
C17—C18—C3	120.34 (11)	C3—C18—H18	120
C9—C19—C20	111.35 (9)	C17—C18—H18	120
C21—C20—C19	111.76 (10)	C9—C19—H19A	109
C22—C21—C20	111.04 (10)	C9—C19—H19B	109
C21—C22—C10	111.49 (9)	C20—C19—H19A	109
O4—C5—H5A	110	C20—C19—H19B	109
O4—C5—H5B	110	H19A—C19—H19B	108
C6—C5—H5A	110	C19—C20—H20A	109
C6—C5—H5B	110	C19—C20—H20B	109
H5A—C5—H5B	108	C21—C20—H20A	109
C5—C6—H6A	109	C21—C20—H20B	109
C5—C6—H6B	109	H20A—C20—H20B	108
C7—C6—H6A	109	C20—C21—H21A	109
C7—C6—H6B	109	C20—C21—H21B	109
H6A—C6—H6B	108	C22—C21—H21A	109
O8—C7—H7A	110	C22—C21—H21B	109
O8—C7—H7B	110	H21A—C21—H21B	108
C6—C7—H7A	110	C10—C22—H22A	109
C6—C7—H7B	110	C10—C22—H22B	109
H7A—C7—H7B	108	C21—C22—H22A	109
O8—C9—H9	108	C21—C22—H22B	109
C10—C9—H9	108	H22A—C22—H22B	108
O1—C2—C3—O4	0.43 (17)	O8—C9—C10—O11	56.26 (12)
C2—C3—O4—C5	126.08 (12)	C9—C10—O11—C12	−156.68 (9)
C3—O4—C5—C6	158.82 (10)	C10—O11—C12—C13	174.72 (9)
O4—C5—C6—C7	61.93 (14)	O11—C12—C13—C14	−69.43 (13)
C5—C6—C7—O8	66.15 (13)	C12—C13—C14—O1	−73.07 (12)
C6—C7—O8—C9	177.12 (9)	C13—C14—O1—C2	−179.30 (9)
C7—O8—C9—C10	65.24 (12)	C14—O1—C2—C3	−82.11 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7B···O4	0.99	2.57	2.9233 (16)	100
C10—H10···O1^i	1.00	2.59	3.5398 (14)	158
C16—H16···O8^ii	0.95	2.58	3.5103 (16)	167

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

(II)

Crystal data

[Li(NCS)(C18H26O4)]	F(000) = 1584
Mr = 371.4	Dx = 1.27 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.3885 (8) Å	Cell parameters from 25 reflections
b = 23.960 (3) Å	θ = 10.1–14.0°
c = 17.744 (2) Å	µ = 0.19 mm^−1
β = 102.507 (8)°	T = 100 K
V = 3896.7 (7) Å^3	Fragment, colourless
Z = 8	0.55 × 0.53 × 0.21 mm

Data collection

Nonius CAD4 diffractometer	Rint = 0.028
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 2.0°
Graphite monochromator	h = −11→10
ω–scans	k = −28→23
10705 measured reflections	l = 0→21
6837 independent reflections	3 standard reflections every 120 min
4556 reflections with I > 2σ(I)	intensity decay: 10%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.135	H-atom parameters not refined
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0582P)^2 + 2.7961P] where P = (Fo^2 + 2Fc^2)/3
6837 reflections	(Δ/σ)max < 0.001
469 parameters	Δρmax = 0.60 e Å^−3
0 restraints	Δρmin = −0.23 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.

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	1.07002 (8)	0.36265 (3)	0.92991 (5)	0.0411 (3)
O1	0.53461 (19)	0.36230 (7)	0.65305 (10)	0.0265 (6)
O2	0.47751 (19)	0.30365 (8)	0.76125 (10)	0.0286 (6)
O3	0.5040 (2)	0.39743 (8)	0.85237 (11)	0.0306 (6)
O4	0.58531 (19)	0.46124 (7)	0.75061 (10)	0.0280 (6)
N1	0.8078 (3)	0.36083 (10)	0.81923 (14)	0.0348 (8)
C1	0.4442 (3)	0.31738 (10)	0.62870 (15)	0.0243 (8)
C2	0.4119 (3)	0.28536 (11)	0.68888 (15)	0.0260 (8)
C3	0.3219 (3)	0.23918 (12)	0.67277 (16)	0.0317 (9)
C4	0.2627 (3)	0.22553 (12)	0.59615 (17)	0.0334 (9)
C5	0.2929 (3)	0.25714 (11)	0.53716 (16)	0.0303 (9)
C6	0.3850 (3)	0.30355 (11)	0.55319 (15)	0.0258 (8)
C7	0.4278 (3)	0.27872 (13)	0.82540 (16)	0.0397 (10)
C8	0.5138 (3)	0.30413 (12)	0.89906 (16)	0.0352 (10)
C9	0.4732 (3)	0.36326 (12)	0.91289 (16)	0.0372 (10)
C10	0.4898 (3)	0.45609 (11)	0.86247 (16)	0.0291 (9)
C11	0.4651 (3)	0.48119 (11)	0.78214 (16)	0.0280 (8)
C12	0.4532 (3)	0.54445 (11)	0.78656 (18)	0.0343 (9)
C13	0.5859 (3)	0.57019 (13)	0.83960 (18)	0.0413 (11)
C14	0.6104 (3)	0.54395 (14)	0.91964 (17)	0.0437 (11)
C15	0.6227 (3)	0.48136 (13)	0.91582 (16)	0.0358 (10)
C16	0.5888 (3)	0.48377 (12)	0.67631 (16)	0.0341 (9)
C17	0.6692 (3)	0.44384 (12)	0.63420 (16)	0.0336 (9)
C18	0.5765 (3)	0.39576 (11)	0.59412 (16)	0.0301 (9)
C19	0.9159 (3)	0.36134 (11)	0.86555 (16)	0.0261 (8)
Li1	0.6031 (5)	0.37609 (18)	0.7694 (2)	0.0278 (12)
S2	0.48941 (8)	0.63296 (4)	0.61450 (5)	0.0427 (3)
O5	1.0247 (2)	0.53093 (8)	0.76265 (13)	0.0374 (7)
O6	1.0623 (2)	0.57289 (8)	0.63639 (11)	0.0333 (7)
O7	1.1018 (2)	0.67803 (8)	0.69877 (10)	0.0314 (6)
O8	1.1011 (2)	0.63899 (8)	0.83498 (11)	0.0330 (6)
N2	0.7815 (3)	0.62691 (10)	0.69357 (15)	0.0369 (8)
C20	0.6603 (3)	0.62949 (11)	0.66027 (16)	0.0274 (9)
C21	1.0685 (3)	0.49395 (12)	0.71441 (19)	0.0358 (10)
C22	1.0939 (3)	0.51632 (12)	0.64589 (18)	0.0350 (9)
C23	1.1475 (3)	0.48382 (13)	0.59438 (19)	0.0449 (11)
C24	1.1727 (3)	0.42697 (13)	0.6098 (2)	0.0485 (11)
C25	1.1439 (3)	0.40421 (14)	0.6763 (2)	0.0509 (13)
C26	1.0918 (3)	0.43698 (13)	0.7291 (2)	0.0450 (10)
C27	1.0918 (3)	0.60051 (13)	0.56989 (17)	0.0373 (10)
C28	1.0269 (3)	0.65805 (12)	0.56481 (17)	0.0357 (9)
C29	1.1054 (3)	0.69916 (12)	0.62356 (16)	0.0335 (9)
C30	1.1671 (3)	0.71280 (11)	0.76200 (15)	0.0285 (9)
C31	1.2251 (3)	0.67363 (11)	0.82889 (16)	0.0286 (9)
C32	1.2894 (3)	0.70584 (12)	0.90163 (17)	0.0356 (10)
C33	1.1850 (4)	0.74834 (13)	0.92191 (18)	0.0433 (11)
C34	1.1284 (4)	0.78681 (13)	0.85400 (18)	0.0443 (11)
C35	1.0580 (3)	0.75407 (12)	0.78232 (17)	0.0355 (10)
C36	1.1257 (3)	0.60205 (13)	0.89998 (18)	0.0390 (10)
C37	1.0029 (3)	0.56049 (13)	0.88848 (19)	0.0428 (11)
C38	1.0158 (4)	0.51127 (13)	0.83900 (19)	0.0436 (11)
Li2	0.9943 (5)	0.61331 (19)	0.7258 (3)	0.0325 (16)
H3	0.300800	0.217100	0.713500	0.0380*
H4	0.200700	0.193900	0.584600	0.0400*
H5	0.251200	0.247500	0.485100	0.0360*
H6	0.406500	0.325300	0.512300	0.0310*
H7A	0.443000	0.237800	0.825800	0.0480*
H7B	0.322300	0.286000	0.820400	0.0480*
H8A	0.499900	0.280900	0.943100	0.0420*
H8B	0.618700	0.303000	0.897900	0.0420*
H9A	0.368200	0.365500	0.913500	0.0450*
H9B	0.530000	0.376400	0.963400	0.0450*
H10	0.401800	0.463300	0.884300	0.0350*
H11	0.372000	0.466100	0.750400	0.0340*
H12A	0.442300	0.560400	0.734100	0.0410*
H12B	0.364700	0.554200	0.805600	0.0410*
H13A	0.571200	0.610900	0.843600	0.0500*
H13B	0.673200	0.564200	0.817700	0.0500*
H14A	0.700900	0.559300	0.952400	0.0530*
H14B	0.528100	0.553800	0.943800	0.0530*
H15A	0.632800	0.465500	0.968300	0.0430*
H15B	0.711300	0.471500	0.897000	0.0430*
H16A	0.638700	0.520400	0.682400	0.0410*
H16B	0.488000	0.489300	0.646100	0.0410*
H17A	0.753500	0.428200	0.671600	0.0400*
H17B	0.708000	0.465000	0.595100	0.0400*
H18A	0.488800	0.410300	0.558100	0.0360*
H18B	0.633200	0.373100	0.564300	0.0360*
H23	1.167100	0.499800	0.548700	0.0540*
H24	1.209600	0.404100	0.574600	0.0580*
H25	1.160000	0.365500	0.686200	0.0610*
H26	1.072200	0.420800	0.774600	0.0540*
H27A	1.048900	0.579100	0.522800	0.0450*
H27B	1.198500	0.603000	0.574000	0.0450*
H28A	0.924600	0.655000	0.570600	0.0430*
H28B	1.024800	0.673100	0.512600	0.0430*
H29A	1.207700	0.703600	0.618300	0.0400*
H29B	1.056900	0.736000	0.615600	0.0400*
H30	1.250300	0.733800	0.748500	0.0340*
H31	1.302600	0.649500	0.815200	0.0340*
H32A	1.317600	0.679300	0.945000	0.0430*
H32B	1.378900	0.725200	0.894700	0.0430*
H33A	1.235400	0.770700	0.966800	0.0520*
H33B	1.102000	0.728900	0.936500	0.0520*
H34A	1.210200	0.809200	0.843100	0.0530*
H34B	1.056000	0.812900	0.867500	0.0530*
H35A	1.024800	0.780000	0.738700	0.0430*
H35B	0.971800	0.733700	0.791700	0.0430*
H36A	1.129200	0.623500	0.948000	0.0470*
H36B	1.219900	0.582400	0.904400	0.0470*
H37A	0.994000	0.546700	0.939800	0.0520*
H37B	0.911200	0.580300	0.865600	0.0520*
H38A	1.104200	0.489500	0.862000	0.0530*
H38B	0.929700	0.486700	0.835300	0.0530*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Li1	0.031 (2)	0.023 (2)	0.026 (2)	−0.0011 (19)	−0.0012 (19)	−0.0012 (18)
Li2	0.023 (2)	0.030 (3)	0.043 (3)	−0.0028 (19)	0.004 (2)	0.007 (2)
S1	0.0297 (4)	0.0454 (5)	0.0409 (4)	0.0019 (3)	−0.0083 (3)	0.0069 (4)
C19	0.0263 (15)	0.0217 (14)	0.0308 (15)	0.0024 (11)	0.0072 (13)	0.0023 (12)
N1	0.0294 (13)	0.0362 (14)	0.0365 (14)	0.0011 (11)	0.0019 (12)	0.0021 (11)
S2	0.0284 (4)	0.0482 (5)	0.0448 (5)	−0.0078 (4)	−0.0066 (3)	0.0174 (4)
C20	0.0294 (16)	0.0223 (14)	0.0319 (15)	−0.0029 (12)	0.0095 (13)	0.0038 (12)
N2	0.0257 (14)	0.0322 (14)	0.0525 (16)	−0.0004 (11)	0.0077 (12)	0.0051 (12)
O1	0.0307 (10)	0.0230 (10)	0.0234 (9)	−0.0075 (8)	0.0004 (8)	0.0000 (8)
O2	0.0306 (10)	0.0285 (10)	0.0243 (10)	−0.0063 (8)	0.0009 (8)	−0.0010 (8)
O3	0.0356 (11)	0.0274 (11)	0.0290 (10)	0.0036 (8)	0.0074 (8)	0.0002 (8)
O4	0.0286 (10)	0.0285 (10)	0.0260 (10)	−0.0002 (8)	0.0039 (8)	0.0015 (8)
O5	0.0284 (11)	0.0249 (11)	0.0589 (14)	−0.0003 (8)	0.0092 (10)	0.0079 (10)
O6	0.0314 (11)	0.0268 (11)	0.0389 (12)	0.0049 (9)	0.0017 (9)	−0.0015 (9)
O7	0.0344 (11)	0.0257 (10)	0.0323 (11)	−0.0100 (8)	0.0034 (9)	−0.0010 (8)
O8	0.0283 (10)	0.0322 (11)	0.0372 (11)	−0.0023 (9)	0.0042 (9)	0.0099 (9)
C1	0.0222 (13)	0.0181 (13)	0.0304 (15)	0.0006 (11)	0.0008 (11)	−0.0043 (11)
C2	0.0233 (14)	0.0241 (14)	0.0285 (15)	0.0017 (11)	0.0013 (11)	−0.0051 (12)
C3	0.0309 (16)	0.0280 (15)	0.0361 (17)	−0.0027 (12)	0.0070 (13)	0.0016 (13)
C4	0.0286 (15)	0.0262 (15)	0.0425 (18)	−0.0045 (12)	0.0014 (13)	−0.0067 (13)
C5	0.0276 (15)	0.0285 (15)	0.0308 (16)	0.0027 (12)	−0.0025 (12)	−0.0099 (13)
C6	0.0280 (14)	0.0212 (14)	0.0266 (14)	0.0019 (11)	0.0024 (11)	−0.0024 (11)
C7	0.0428 (18)	0.0431 (19)	0.0329 (17)	−0.0105 (15)	0.0075 (14)	0.0065 (14)
C8	0.0405 (17)	0.0353 (17)	0.0289 (16)	−0.0019 (14)	0.0055 (13)	0.0062 (13)
C9	0.0445 (18)	0.0404 (18)	0.0292 (16)	0.0035 (14)	0.0134 (14)	0.0071 (14)
C10	0.0258 (15)	0.0305 (15)	0.0320 (16)	−0.0001 (12)	0.0084 (12)	−0.0034 (12)
C11	0.0206 (13)	0.0277 (15)	0.0350 (16)	−0.0023 (11)	0.0047 (12)	−0.0061 (12)
C12	0.0308 (16)	0.0262 (15)	0.0456 (18)	−0.0043 (12)	0.0078 (13)	0.0001 (13)
C13	0.0414 (18)	0.0341 (17)	0.053 (2)	−0.0134 (14)	0.0205 (16)	−0.0148 (15)
C14	0.0383 (18)	0.058 (2)	0.0383 (18)	−0.0164 (16)	0.0157 (15)	−0.0211 (16)
C15	0.0270 (15)	0.054 (2)	0.0261 (15)	−0.0100 (14)	0.0048 (12)	−0.0055 (14)
C16	0.0442 (17)	0.0245 (15)	0.0331 (16)	−0.0075 (13)	0.0070 (13)	0.0009 (13)
C17	0.0374 (17)	0.0366 (17)	0.0273 (15)	−0.0096 (13)	0.0084 (13)	0.0039 (13)
C18	0.0333 (16)	0.0286 (15)	0.0270 (15)	−0.0037 (12)	0.0032 (12)	0.0021 (12)
C21	0.0182 (14)	0.0283 (16)	0.056 (2)	−0.0053 (12)	−0.0029 (13)	0.0015 (15)
C22	0.0166 (13)	0.0302 (16)	0.0508 (19)	0.0016 (12)	−0.0091 (13)	−0.0141 (15)
C23	0.0338 (17)	0.0408 (19)	0.050 (2)	0.0024 (14)	−0.0131 (15)	−0.0136 (16)
C24	0.0306 (17)	0.0361 (19)	0.066 (2)	0.0053 (14)	−0.0180 (16)	−0.0194 (17)
C25	0.0298 (17)	0.0292 (17)	0.084 (3)	−0.0004 (14)	−0.0092 (17)	−0.0116 (19)
C26	0.0228 (15)	0.0294 (17)	0.077 (2)	−0.0030 (13)	−0.0019 (16)	0.0057 (16)
C27	0.0302 (16)	0.0429 (18)	0.0351 (17)	−0.0018 (14)	−0.0014 (13)	−0.0073 (14)
C28	0.0359 (16)	0.0385 (17)	0.0294 (16)	−0.0032 (14)	0.0000 (13)	0.0047 (13)
C29	0.0355 (16)	0.0307 (16)	0.0329 (16)	−0.0037 (13)	0.0041 (13)	0.0070 (13)
C30	0.0272 (15)	0.0250 (15)	0.0336 (16)	−0.0049 (12)	0.0070 (12)	−0.0026 (12)
C31	0.0196 (14)	0.0244 (14)	0.0424 (17)	−0.0017 (11)	0.0079 (12)	−0.0007 (12)
C32	0.0322 (16)	0.0338 (17)	0.0366 (17)	0.0004 (13)	−0.0019 (13)	0.0016 (13)
C33	0.0488 (19)	0.0423 (19)	0.0364 (18)	0.0016 (15)	0.0042 (15)	−0.0052 (14)
C34	0.051 (2)	0.0352 (17)	0.0459 (19)	0.0084 (15)	0.0089 (16)	−0.0047 (15)
C35	0.0313 (16)	0.0322 (16)	0.0410 (18)	0.0048 (13)	0.0037 (13)	0.0046 (13)
C36	0.0353 (17)	0.0415 (18)	0.0415 (18)	0.0015 (14)	0.0114 (14)	0.0116 (15)
C37	0.0397 (18)	0.0435 (19)	0.048 (2)	−0.0001 (15)	0.0155 (15)	0.0151 (16)
C38	0.0383 (18)	0.0340 (18)	0.061 (2)	−0.0017 (14)	0.0164 (16)	0.0196 (16)

Geometric parameters (Å, º)

S1—C19	1.638 (3)	C11—H11	0.9993
S2—C20	1.636 (3)	C12—H12A	0.9908
O1—C18	1.438 (3)	C12—H12B	0.9903
O1—Li1	2.052 (4)	C13—H13A	0.9898
O1—C1	1.381 (3)	C13—H13B	0.9906
O2—C7	1.449 (3)	C14—H14A	0.9905
O2—Li1	2.086 (5)	C14—H14B	0.9899
O2—C2	1.370 (3)	C15—H15A	0.9911
O3—C9	1.429 (3)	C15—H15B	0.9897
O3—Li1	1.972 (5)	C16—H16A	0.9897
O3—C10	1.427 (3)	C16—H16B	0.9903
O4—C11	1.445 (3)	C17—H17A	0.9898
O4—Li1	2.068 (5)	C17—H17B	0.9902
O4—C16	1.432 (3)	C18—H18A	0.9899
O5—Li2	2.079 (5)	C18—H18B	0.9900
O5—C38	1.454 (4)	C21—C22	1.396 (4)
O5—C21	1.356 (4)	C21—C26	1.398 (4)
O6—C22	1.390 (3)	C22—C23	1.376 (4)
O6—C27	1.431 (4)	C23—C24	1.399 (4)
O6—Li2	2.074 (5)	C24—C25	1.379 (5)
O7—C29	1.435 (3)	C25—C26	1.390 (5)
O7—Li2	1.965 (5)	C27—C28	1.502 (4)
O7—C30	1.425 (3)	C28—C29	1.506 (4)
O8—C36	1.432 (4)	C30—C31	1.519 (4)
O8—C31	1.453 (3)	C30—C35	1.522 (4)
O8—Li2	2.073 (5)	C31—C32	1.513 (4)
N1—C19	1.159 (4)	C32—C33	1.510 (5)
N1—Li1	1.968 (5)	C33—C34	1.519 (4)
N2—C20	1.165 (4)	C34—C35	1.518 (4)
N2—Li2	1.982 (6)	C36—C37	1.504 (4)
C1—C2	1.400 (4)	C37—C38	1.491 (5)
C1—C6	1.375 (4)	C23—H23	0.9498
C2—C3	1.384 (4)	C24—H24	0.9508
C3—C4	1.392 (4)	C25—H25	0.9500
C4—C5	1.370 (4)	C26—H26	0.9488
C5—C6	1.399 (4)	C27—H27A	0.9888
C7—C8	1.508 (4)	C27—H27B	0.9903
C8—C9	1.501 (4)	C28—H28A	0.9905
C10—C11	1.518 (4)	C28—H28B	0.9903
C10—C15	1.519 (4)	C29—H29A	0.9906
C11—C12	1.523 (4)	C29—H29B	0.9892
C12—C13	1.520 (4)	C30—H30	1.0009
C13—C14	1.524 (4)	C31—H31	0.9996
C14—C15	1.507 (5)	C32—H32A	0.9892
C16—C17	1.513 (4)	C32—H32B	0.9905
C17—C18	1.524 (4)	C33—H33A	0.9910
C3—H3	0.9505	C33—H33B	0.9892
C4—H4	0.9505	C34—H34A	0.9896
C5—H5	0.9504	C34—H34B	0.9903
C6—H6	0.9498	C35—H35A	0.9888
C7—H7A	0.9906	C35—H35B	0.9895
C7—H7B	0.9906	C36—H36A	0.9895
C8—H8B	0.9899	C36—H36B	0.9899
C8—H8A	0.9908	C37—H37A	0.9891
C9—H9B	0.9898	C37—H37B	0.9899
C9—H9A	0.9896	C38—H38A	0.9903
C10—H10	1.0005	C38—H38B	0.9906
C1—O1—C18	117.0 (2)	O1—C18—H18A	110.21
C1—O1—Li1	118.54 (19)	C17—C18—H18A	110.27
C18—O1—Li1	124.5 (2)	C17—C18—H18B	110.19
C2—O2—C7	116.6 (2)	S2—C20—N2	179.3 (3)
C2—O2—Li1	117.63 (18)	O5—C21—C22	115.5 (3)
C7—O2—Li1	124.19 (19)	O5—C21—C26	125.2 (3)
C9—O3—C10	115.5 (2)	C22—C21—C26	119.2 (3)
C9—O3—Li1	128.1 (2)	C21—C22—C23	121.1 (3)
C10—O3—Li1	114.9 (2)	O6—C22—C23	124.8 (3)
C11—O4—C16	114.0 (2)	O6—C22—C21	114.1 (3)
C11—O4—Li1	107.84 (19)	C22—C23—C24	119.4 (3)
C16—O4—Li1	120.22 (18)	C23—C24—C25	119.7 (3)
C38—O5—Li2	124.7 (2)	C24—C25—C26	121.1 (3)
C21—O5—C38	117.6 (2)	C21—C26—C25	119.3 (3)
C21—O5—Li2	117.5 (2)	O6—C27—C28	109.0 (2)
C27—O6—Li2	124.1 (2)	C27—C28—C29	115.3 (2)
C22—O6—C27	118.5 (2)	O7—C29—C28	107.9 (2)
C22—O6—Li2	117.1 (2)	C31—C30—C35	111.2 (2)
C29—O7—Li2	128.5 (2)	O7—C30—C31	105.9 (2)
C29—O7—C30	115.7 (2)	O7—C30—C35	111.7 (2)
C30—O7—Li2	115.2 (2)	O8—C31—C30	104.7 (2)
C31—O8—C36	114.9 (2)	O8—C31—C32	114.0 (2)
C31—O8—Li2	109.5 (2)	C30—C31—C32	111.2 (2)
C36—O8—Li2	122.0 (2)	C31—C32—C33	112.8 (2)
C19—N1—Li1	159.4 (3)	C32—C33—C34	110.7 (3)
C20—N2—Li2	165.4 (3)	C33—C34—C35	111.4 (3)
O1—C1—C2	114.1 (2)	C30—C35—C34	109.9 (2)
O1—C1—C6	125.7 (2)	O8—C36—C37	108.3 (2)
C2—C1—C6	120.2 (2)	C36—C37—C38	116.5 (3)
C1—C2—C3	120.3 (2)	O5—C38—C37	108.7 (2)
O2—C2—C3	125.4 (2)	C22—C23—H23	120.33
O2—C2—C1	114.3 (2)	C24—C23—H23	120.23
C2—C3—C4	119.1 (3)	C23—C24—H24	120.18
C3—C4—C5	120.8 (3)	C25—C24—H24	120.07
C4—C5—C6	120.3 (3)	C24—C25—H25	119.44
C1—C6—C5	119.4 (2)	C26—C25—H25	119.47
O2—C7—C8	108.1 (2)	C21—C26—H26	120.41
C7—C8—C9	114.6 (2)	C25—C26—H26	120.27
O3—C9—C8	108.5 (2)	C28—C27—H27A	109.86
O3—C10—C11	105.8 (2)	O6—C27—H27B	109.90
O3—C10—C15	112.6 (2)	H27A—C27—H27B	108.29
C11—C10—C15	111.4 (2)	C28—C27—H27B	109.87
O4—C11—C10	105.0 (2)	O6—C27—H27A	109.92
C10—C11—C12	110.1 (2)	H28A—C28—H28B	107.49
O4—C11—C12	114.9 (2)	C27—C28—H28A	108.42
C11—C12—C13	112.1 (2)	C27—C28—H28B	108.42
C12—C13—C14	110.3 (2)	C29—C28—H28B	108.48
C13—C14—C15	111.5 (2)	C29—C28—H28A	108.46
C10—C15—C14	111.4 (2)	O7—C29—H29B	110.17
O4—C16—C17	109.3 (2)	C28—C29—H29B	110.10
C16—C17—C18	114.4 (2)	O7—C29—H29A	110.13
O1—C18—C17	107.5 (2)	H29A—C29—H29B	108.45
S1—C19—N1	179.0 (3)	C28—C29—H29A	110.13
C4—C3—H3	120.47	C31—C30—H30	109.35
C2—C3—H3	120.42	O7—C30—H30	109.30
C5—C4—H4	119.62	C35—C30—H30	109.28
C3—C4—H4	119.63	C32—C31—H31	108.99
C6—C5—H5	119.80	O8—C31—H31	108.96
C4—C5—H5	119.88	C30—C31—H31	108.92
C5—C6—H6	120.32	C31—C32—H32A	109.02
C1—C6—H6	120.27	C31—C32—H32B	109.00
O2—C7—H7A	110.07	H32A—C32—H32B	107.84
H7A—C7—H7B	108.34	C33—C32—H32B	109.01
C8—C7—H7B	110.11	C33—C32—H32A	109.05
O2—C7—H7B	110.05	C34—C33—H33B	109.47
C8—C7—H7A	110.13	C32—C33—H33B	109.49
C7—C8—H8B	108.62	C32—C33—H33A	109.54
H8A—C8—H8B	107.61	H33A—C33—H33B	108.08
C9—C8—H8A	108.65	C34—C33—H33A	109.49
C9—C8—H8B	108.56	C33—C34—H34A	109.33
C7—C8—H8A	108.64	C33—C34—H34B	109.37
H9A—C9—H9B	108.39	C35—C34—H34A	109.38
C8—C9—H9A	109.99	C35—C34—H34B	109.37
C8—C9—H9B	110.01	H34A—C34—H34B	107.91
O3—C9—H9B	109.95	H35A—C35—H35B	108.11
O3—C9—H9A	109.96	C30—C35—H35A	109.69
O3—C10—H10	109.04	C30—C35—H35B	109.65
C15—C10—H10	109.00	C34—C35—H35B	109.72
C11—C10—H10	108.91	C34—C35—H35A	109.71
O4—C11—H11	108.86	O8—C36—H36B	110.07
C12—C11—H11	108.91	H36A—C36—H36B	108.44
C10—C11—H11	108.84	O8—C36—H36A	109.99
C11—C12—H12B	109.19	C37—C36—H36B	109.96
C13—C12—H12B	109.20	C37—C36—H36A	110.02
C13—C12—H12A	109.22	C38—C37—H37A	108.17
C11—C12—H12A	109.22	C36—C37—H37B	108.14
H12A—C12—H12B	107.81	C36—C37—H37A	108.15
C14—C13—H13A	109.56	C38—C37—H37B	108.19
C14—C13—H13B	109.57	H37A—C37—H37B	107.36
C12—C13—H13B	109.58	O5—C38—H38B	109.97
C12—C13—H13A	109.63	C37—C38—H38B	109.87
H13A—C13—H13B	108.12	O5—C38—H38A	110.03
C13—C14—H14B	109.31	H38A—C38—H38B	108.26
C13—C14—H14A	109.32	C37—C38—H38A	109.98
H14A—C14—H14B	107.95	O4—Li1—N1	107.0 (2)
C15—C14—H14A	109.37	O2—Li1—O3	85.21 (19)
C15—C14—H14B	109.35	O2—Li1—O4	141.7 (3)
C10—C15—H15A	109.34	O2—Li1—N1	111.0 (2)
H15A—C15—H15B	108.01	O3—Li1—O4	80.20 (17)
C14—C15—H15A	109.39	O3—Li1—N1	106.59 (19)
C14—C15—H15B	109.33	O1—Li1—O3	134.2 (3)
C10—C15—H15B	109.36	O1—Li1—O4	89.99 (16)
C17—C16—H16B	109.75	O1—Li1—N1	119.0 (2)
C17—C16—H16A	109.86	O1—Li1—O2	75.34 (15)
H16A—C16—H16B	108.34	O5—Li2—O7	141.5 (3)
O4—C16—H16B	109.83	O5—Li2—O8	89.0 (2)
O4—C16—H16A	109.79	O5—Li2—O6	75.72 (18)
C16—C17—H17B	108.72	O6—Li2—O7	85.5 (2)
C18—C17—H17B	108.64	O6—Li2—O8	133.4 (3)
H17A—C17—H17B	107.55	O6—Li2—N2	108.3 (3)
C16—C17—H17A	108.69	O7—Li2—O8	79.85 (19)
C18—C17—H17A	108.64	O7—Li2—N2	109.8 (2)
O1—C18—H18B	110.25	O8—Li2—N2	118.3 (3)
H18A—C18—H18B	108.44	O5—Li2—N2	107.9 (2)
O1—C1—C2—C3	179.7 (3)	O5—C21—C22—C23	175.9 (3)
O1—C1—C2—O2	−1 (3)	O5—C21—C22—O6	−3.3 (4)
O1—C1—C6—C5	−178.9 (3)	O5—C21—C26—C25	−176.7 (3)
C1—C2—C3—C4	−0.8 (4)	C21—C22—C23—C24	2 (5)
C1—C2—O2—C7	169.1 (2)	C21—C22—O6—C27	176.8 (2)
C2—C1—C6—C5	−0.3 (4)	C22—C21—C26—C25	1.9 (4)
C2—C3—C4—C5	0.1 (5)	C22—C23—C24—C25	−0.1 (5)
C2—O2—C7—C8	179.6 (2)	C22—O6—C27—C28	170.7 (2)
O2—C2—C3—C4	−180 (3)	O6—C22—C23—C24	−178.9 (3)
O2—C7—C8—C9	72.9 (3)	O6—C27—C28—C29	72.7 (3)
C3—C4—C5—C6	0.5 (4)	C23—C24—C25—C26	−0.8 (5)
C4—C5—C6—C1	−0.4 (4)	C24—C25—C26—C21	−0.1 (5)
C6—C1—C2—C3	0.9 (4)	C26—C21—C22—C23	−2.9 (5)
C6—C1—C2—O2	−179.9 (2)	C26—C21—C22—O6	177.9 (3)
C7—C8—C9—O3	−62.8 (3)	C27—C28—C29—O7	−60.8 (3)
C7—O2—C2—C3	−11.7 (4)	C27—O6—C22—C23	−2.3 (4)
C8—C9—O3—C10	−172 (2)	C28—C29—O7—C30	−177.9 (2)
C9—O3—C10—C11	−157.3 (2)	C29—O7—C30—C31	−149.9 (2)
C9—O3—C10—C15	80.8 (3)	C29—O7—C30—C35	88.9 (3)
O3—C10—C11—C12	−178.2 (2)	O7—C30—C31—C32	−176.5 (2)
O3—C10—C11—O4	−54 (3)	O7—C30—C31—O8	−53 (3)
O3—C10—C15—C14	174.8 (2)	O7—C30—C35—C34	175.2 (2)
C10—C11—C12—C13	55.9 (3)	C30—C31—C32—C33	53.5 (3)
C10—C11—O4—C16	−175.5 (2)	C30—C31—O8—C36	−173.9 (2)
C11—C10—C15—C14	56.2 (3)	C31—C30—C35—C34	57.1 (3)
C11—C12—C13—C14	−55.6 (3)	C31—C32—C33—C34	−53.7 (3)
C11—O4—C16—C17	−155 (2)	C31—O8—C36—C37	−167.1 (2)
O4—C11—C12—C13	−62.5 (3)	O8—C31—C32—C33	−64.6 (3)
O4—C16—C17—C18	82.2 (3)	O8—C36—C37—C38	82.8 (3)
C12—C13—C14—C15	55.2 (3)	C32—C33—C34—C35	55.8 (4)
C13—C14—C15—C10	−55.8 (3)	C33—C34—C35—C30	−57.6 (4)
C15—C10—C11—C12	−55.5 (3)	C35—C30—C31—C32	−54.9 (3)
C15—C10—C11—O4	68.7 (3)	C35—C30—C31—O8	68.6 (3)
C16—C17—C18—O1	−64.4 (3)	C36—C37—C38—O5	−59.6 (4)
C16—O4—C11—C12	−54.3 (3)	C36—O8—C31—C32	−52.2 (3)
C17—C18—O1—C1	177.4 (2)	C37—C38—O5—C21	166 (3)
C18—O1—C1—C2	177.8 (2)	C38—O5—C21—C22	−171.9 (3)
C18—O1—C1—C6	−3.5 (4)	C38—O5—C21—C26	6.8 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···S2^i	0.95	2.82	3.752 (3)	166
C7—H7A···S2^ii	0.99	2.75	3.685 (3)	158
C9—H9A···S1^iii	0.99	2.88	3.862 (3)	173
C12—H12A···S2	0.99	2.85	3.793 (3)	159
C27—H27B···S2^iv	0.99	2.76	3.726 (3)	164

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, y−1/2, −z+3/2; (iii) x−1, y, z; (iv) x+1, y, z.