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The structures of a 14-crown-4 ether containing both benzo and cyclo­hexano substituents, 2,6,13,17-tetraoxatricyclo-[16.4.0.07,12]docosa-1(18),19,21-triene, C18H26O4, and its lith­ium complex, [2,6,13,17-tetraoxatricyclo[16.4.0.07,12]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].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100009033/fr1290sup1.cif
Contains datablocks global, I, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100009033/fr1290Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100009033/fr1290IIsup3.hkl
Contains datablock II

CCDC references: 150773; 150774

Computing details top

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) top
Crystal data top
C18H26O4F(000) = 664
Mr = 306.4Dx = 1.26 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 9.9888 (11) ÅCell parameters from 25 reflections
b = 15.5672 (9) Åθ = 10.1–14.4°
c = 10.9050 (9) ŵ = 0.09 mm1
β = 107.841 (7)°T = 163 K
V = 1614.2 (2) Å3Prism, colourless
Z = 40.43 × 0.37 × 0.36 mm
Data collection top
Nonius CAD4
diffractometer
Rint = 0.021
Radiation source: fine-focus sealed tubeθmax = 27.5°, θmin = 2.3°
Graphite monochromatorh = 012
ω–scansk = 1020
4433 measured reflectionsl = 1413
3677 independent reflections3 standard reflections every 120 min
2935 reflections with I > 2σ(I) intensity decay: none
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100H-atom parameters not refined
S = 1.03 w = 1/[σ2(Fo2) + (0.0443P)2 + 0.429P]
where P = (Fo2 + 2Fc2)/3
3677 reflections(Δ/σ)max < 0.001
199 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.24 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
O10.02977 (8)0.50591 (5)0.28511 (8)0.02213 (19)
C20.16141 (12)0.51025 (7)0.26878 (11)0.0185 (2)
C30.27383 (12)0.46327 (7)0.34711 (11)0.0202 (2)
O40.25162 (10)0.41149 (6)0.44142 (9)0.0268 (2)
C50.29291 (14)0.32301 (8)0.43957 (12)0.0247 (3)
H5A0.38150.31910.41710.030*
H5B0.21920.29060.37450.030*
C60.31347 (13)0.28578 (8)0.57208 (12)0.0249 (3)
H6A0.38710.31910.63580.030*
H6B0.34740.22590.57370.030*
C70.18109 (13)0.28626 (8)0.61168 (11)0.0226 (3)
H7A0.20230.26740.70230.027*
H7B0.14100.34490.60380.027*
O80.08379 (8)0.22881 (5)0.52851 (8)0.02079 (19)
C90.04501 (12)0.21903 (7)0.55798 (11)0.0183 (2)
H90.02220.20160.65040.022*
C100.13192 (12)0.30154 (7)0.53830 (11)0.0184 (2)
H100.07770.34690.59800.022*
O110.15526 (9)0.32837 (5)0.40792 (8)0.02013 (19)
C120.18412 (13)0.41780 (7)0.38833 (12)0.0222 (3)
H12A0.10840.45180.44860.027*
H12B0.27420.43190.40390.027*
C130.19275 (12)0.43860 (8)0.25042 (12)0.0228 (3)
H13A0.25950.39840.19220.027*
H13B0.23060.49740.22990.027*
C140.05251 (12)0.43289 (7)0.22480 (11)0.0202 (2)
H14A0.00380.37900.26110.024*
H14B0.06650.43350.13090.024*
C150.18308 (13)0.56648 (7)0.17765 (12)0.0223 (3)
H150.10630.59860.12450.027*
C160.31557 (14)0.57619 (8)0.16336 (12)0.0258 (3)
H160.32950.61440.10040.031*
C170.42707 (13)0.52973 (8)0.24170 (13)0.0268 (3)
H170.51820.53620.23270.032*
C180.40699 (13)0.47375 (8)0.33333 (12)0.0254 (3)
H180.48440.44230.38700.031*
C190.12567 (12)0.14622 (7)0.47504 (12)0.0208 (2)
H19A0.06850.09310.49420.025*
H19B0.14260.16040.38300.025*
C200.26653 (13)0.13050 (8)0.49947 (13)0.0247 (3)
H20A0.32000.08640.43860.030*
H20B0.24910.10820.58800.030*
C210.35404 (13)0.21249 (8)0.48322 (12)0.0238 (3)
H21A0.38300.23040.39170.029*
H21B0.44010.20110.50750.029*
C220.27063 (13)0.28478 (8)0.56684 (12)0.0216 (2)
H22A0.25050.26940.65880.026*
H22B0.32780.33790.55080.026*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0183 (4)0.0187 (4)0.0323 (5)0.0023 (3)0.0121 (3)0.0061 (3)
C20.0184 (5)0.0156 (5)0.0234 (5)0.0016 (4)0.0091 (4)0.0041 (4)
C30.0233 (6)0.0179 (5)0.0221 (6)0.0009 (4)0.0109 (5)0.0008 (4)
O40.0361 (5)0.0209 (4)0.0301 (5)0.0082 (4)0.0201 (4)0.0086 (4)
C50.0279 (6)0.0192 (6)0.0315 (7)0.0059 (5)0.0157 (5)0.0046 (5)
C60.0187 (6)0.0250 (6)0.0297 (6)0.0012 (5)0.0054 (5)0.0075 (5)
C70.0225 (6)0.0243 (6)0.0206 (6)0.0037 (5)0.0060 (5)0.0004 (5)
O80.0180 (4)0.0225 (4)0.0230 (4)0.0009 (3)0.0081 (3)0.0035 (3)
C90.0189 (5)0.0187 (5)0.0189 (5)0.0004 (4)0.0080 (4)0.0007 (4)
C100.0212 (6)0.0168 (5)0.0190 (5)0.0012 (4)0.0086 (4)0.0024 (4)
O110.0269 (4)0.0141 (4)0.0211 (4)0.0006 (3)0.0098 (3)0.0010 (3)
C120.0226 (6)0.0146 (5)0.0327 (6)0.0026 (4)0.0132 (5)0.0027 (5)
C130.0172 (5)0.0203 (6)0.0303 (6)0.0018 (4)0.0064 (5)0.0056 (5)
C140.0210 (6)0.0166 (5)0.0237 (6)0.0021 (4)0.0078 (5)0.0018 (4)
C150.0256 (6)0.0181 (5)0.0234 (6)0.0020 (5)0.0075 (5)0.0007 (4)
C160.0336 (7)0.0205 (6)0.0285 (6)0.0032 (5)0.0170 (5)0.0021 (5)
C170.0222 (6)0.0272 (6)0.0349 (7)0.0050 (5)0.0145 (5)0.0012 (5)
C180.0184 (6)0.0285 (6)0.0287 (6)0.0020 (5)0.0060 (5)0.0028 (5)
C190.0227 (6)0.0154 (5)0.0256 (6)0.0016 (4)0.0094 (5)0.0013 (4)
C200.0265 (6)0.0183 (6)0.0317 (6)0.0043 (5)0.0124 (5)0.0033 (5)
C210.0194 (6)0.0246 (6)0.0293 (6)0.0017 (5)0.0104 (5)0.0011 (5)
C220.0236 (6)0.0200 (6)0.0249 (6)0.0014 (5)0.0129 (5)0.0014 (5)
Geometric parameters (Å, º) top
O1—C21.3815 (13)C5—H5B0.99
O1—C141.4384 (13)C6—H6A0.99
C2—C151.3902 (16)C6—H6B0.99
C2—C31.3920 (16)C7—H7A0.99
C3—O41.3772 (14)C7—H7B0.99
C3—C181.3932 (16)C9—H91.00
O4—C51.4398 (14)C10—H101.00
C5—C61.5114 (17)C12—H12A0.99
C6—C71.5116 (16)C12—H12B0.99
C7—O81.4237 (14)C13—H13A0.99
O8—C91.4266 (13)C13—H13B0.99
C9—C191.5183 (16)C14—H14A0.99
C9—C101.5282 (16)C14—H14B0.99
C10—O111.4308 (13)C15—H150.95
C10—C221.5326 (15)C16—H160.95
O11—C121.4244 (13)C17—H170.95
C12—C131.5148 (17)C18—H180.95
C13—C141.5127 (15)C19—H19A0.99
C15—C161.3874 (17)C19—H19B0.99
C16—C171.3822 (19)C20—H20A0.99
C17—C181.3860 (18)C20—H20B0.99
C19—C201.5298 (16)C21—H21A0.99
C20—C211.5262 (17)C21—H21B0.99
C21—C221.5254 (17)C22—H22A0.99
C5—H5A0.99C22—H22B0.99
C2—O1—C14114.38 (8)C19—C9—H9108
O1—C2—C15119.06 (10)O11—C10—H10109
O1—C2—C3121.06 (10)C9—C10—H10109
C15—C2—C3119.77 (11)C22—C10—H10109
O4—C3—C2118.78 (10)O11—C12—H12A110
O4—C3—C18121.78 (11)O11—C12—H12B110
C2—C3—C18119.32 (11)C13—C12—H12A110
C3—O4—C5115.92 (9)C13—C12—H12B110
O4—C5—C6108.00 (10)H12A—C12—H12B108
C5—C6—C7113.37 (10)C12—C13—H13A109
O8—C7—C6107.52 (10)C12—C13—H13B109
C7—O8—C9114.22 (8)C14—C13—H13A109
O8—C9—C19107.22 (9)C14—C13—H13B109
O8—C9—C10113.04 (9)H13A—C13—H13B108
C19—C9—C10111.64 (9)O1—C14—H14A110
O11—C10—C9107.31 (9)O1—C14—H14B110
O11—C10—C22111.68 (9)C13—C14—H14A110
C9—C10—C22109.78 (9)C13—C14—H14B110
C12—O11—C10113.47 (9)H14A—C14—H14B108
O11—C12—C13107.78 (10)C2—C15—H15120
C14—C13—C12113.36 (10)C16—C15—H15120
O1—C14—C13107.51 (9)C15—C16—H16120
C16—C15—C2120.78 (11)C17—C16—H16120
C17—C16—C15119.29 (11)C16—C17—H17120
C16—C17—C18120.50 (11)C18—C17—H17120
C17—C18—C3120.34 (11)C3—C18—H18120
C9—C19—C20111.35 (9)C17—C18—H18120
C21—C20—C19111.76 (10)C9—C19—H19A109
C22—C21—C20111.04 (10)C9—C19—H19B109
C21—C22—C10111.49 (9)C20—C19—H19A109
O4—C5—H5A110C20—C19—H19B109
O4—C5—H5B110H19A—C19—H19B108
C6—C5—H5A110C19—C20—H20A109
C6—C5—H5B110C19—C20—H20B109
H5A—C5—H5B108C21—C20—H20A109
C5—C6—H6A109C21—C20—H20B109
C5—C6—H6B109H20A—C20—H20B108
C7—C6—H6A109C20—C21—H21A109
C7—C6—H6B109C20—C21—H21B109
H6A—C6—H6B108C22—C21—H21A109
O8—C7—H7A110C22—C21—H21B109
O8—C7—H7B110H21A—C21—H21B108
C6—C7—H7A110C10—C22—H22A109
C6—C7—H7B110C10—C22—H22B109
H7A—C7—H7B108C21—C22—H22A109
O8—C9—H9108C21—C22—H22B109
C10—C9—H9108H22A—C22—H22B108
O1—C2—C3—O40.43 (17)O8—C9—C10—O1156.26 (12)
C2—C3—O4—C5126.08 (12)C9—C10—O11—C12156.68 (9)
C3—O4—C5—C6158.82 (10)C10—O11—C12—C13174.72 (9)
O4—C5—C6—C761.93 (14)O11—C12—C13—C1469.43 (13)
C5—C6—C7—O866.15 (13)C12—C13—C14—O173.07 (12)
C6—C7—O8—C9177.12 (9)C13—C14—O1—C2179.30 (9)
C7—O8—C9—C1065.24 (12)C14—O1—C2—C382.11 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7B···O40.992.572.9233 (16)100
C10—H10···O1i1.002.593.5398 (14)158
C16—H16···O8ii0.952.583.5103 (16)167
Symmetry codes: (i) x, y+1, z+1; (ii) x+1/2, y+1/2, z+1/2.
(II) top
Crystal data top
[Li(NCS)(C18H26O4)]F(000) = 1584
Mr = 371.4Dx = 1.27 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 9.3885 (8) ÅCell parameters from 25 reflections
b = 23.960 (3) Åθ = 10.1–14.0°
c = 17.744 (2) ŵ = 0.19 mm1
β = 102.507 (8)°T = 100 K
V = 3896.7 (7) Å3Fragment, colourless
Z = 80.55 × 0.53 × 0.21 mm
Data collection top
Nonius CAD4
diffractometer
Rint = 0.028
Radiation source: fine-focus sealed tubeθmax = 25.0°, θmin = 2.0°
Graphite monochromatorh = 1110
ω–scansk = 2823
10705 measured reflectionsl = 021
6837 independent reflections3 standard reflections every 120 min
4556 reflections with I > 2σ(I) intensity decay: 10%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135H-atom parameters not refined
S = 1.01 w = 1/[σ2(Fo2) + (0.0582P)2 + 2.7961P]
where P = (Fo2 + 2Fc2)/3
6837 reflections(Δ/σ)max < 0.001
469 parametersΔρmax = 0.60 e Å3
0 restraintsΔρmin = 0.23 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
S11.07002 (8)0.36265 (3)0.92991 (5)0.0411 (3)
O10.53461 (19)0.36230 (7)0.65305 (10)0.0265 (6)
O20.47751 (19)0.30365 (8)0.76125 (10)0.0286 (6)
O30.5040 (2)0.39743 (8)0.85237 (11)0.0306 (6)
O40.58531 (19)0.46124 (7)0.75061 (10)0.0280 (6)
N10.8078 (3)0.36083 (10)0.81923 (14)0.0348 (8)
C10.4442 (3)0.31738 (10)0.62870 (15)0.0243 (8)
C20.4119 (3)0.28536 (11)0.68888 (15)0.0260 (8)
C30.3219 (3)0.23918 (12)0.67277 (16)0.0317 (9)
C40.2627 (3)0.22553 (12)0.59615 (17)0.0334 (9)
C50.2929 (3)0.25714 (11)0.53716 (16)0.0303 (9)
C60.3850 (3)0.30355 (11)0.55319 (15)0.0258 (8)
C70.4278 (3)0.27872 (13)0.82540 (16)0.0397 (10)
C80.5138 (3)0.30413 (12)0.89906 (16)0.0352 (10)
C90.4732 (3)0.36326 (12)0.91289 (16)0.0372 (10)
C100.4898 (3)0.45609 (11)0.86247 (16)0.0291 (9)
C110.4651 (3)0.48119 (11)0.78214 (16)0.0280 (8)
C120.4532 (3)0.54445 (11)0.78656 (18)0.0343 (9)
C130.5859 (3)0.57019 (13)0.83960 (18)0.0413 (11)
C140.6104 (3)0.54395 (14)0.91964 (17)0.0437 (11)
C150.6227 (3)0.48136 (13)0.91582 (16)0.0358 (10)
C160.5888 (3)0.48377 (12)0.67631 (16)0.0341 (9)
C170.6692 (3)0.44384 (12)0.63420 (16)0.0336 (9)
C180.5765 (3)0.39576 (11)0.59412 (16)0.0301 (9)
C190.9159 (3)0.36134 (11)0.86555 (16)0.0261 (8)
Li10.6031 (5)0.37609 (18)0.7694 (2)0.0278 (12)
S20.48941 (8)0.63296 (4)0.61450 (5)0.0427 (3)
O51.0247 (2)0.53093 (8)0.76265 (13)0.0374 (7)
O61.0623 (2)0.57289 (8)0.63639 (11)0.0333 (7)
O71.1018 (2)0.67803 (8)0.69877 (10)0.0314 (6)
O81.1011 (2)0.63899 (8)0.83498 (11)0.0330 (6)
N20.7815 (3)0.62691 (10)0.69357 (15)0.0369 (8)
C200.6603 (3)0.62949 (11)0.66027 (16)0.0274 (9)
C211.0685 (3)0.49395 (12)0.71441 (19)0.0358 (10)
C221.0939 (3)0.51632 (12)0.64589 (18)0.0350 (9)
C231.1475 (3)0.48382 (13)0.59438 (19)0.0449 (11)
C241.1727 (3)0.42697 (13)0.6098 (2)0.0485 (11)
C251.1439 (3)0.40421 (14)0.6763 (2)0.0509 (13)
C261.0918 (3)0.43698 (13)0.7291 (2)0.0450 (10)
C271.0918 (3)0.60051 (13)0.56989 (17)0.0373 (10)
C281.0269 (3)0.65805 (12)0.56481 (17)0.0357 (9)
C291.1054 (3)0.69916 (12)0.62356 (16)0.0335 (9)
C301.1671 (3)0.71280 (11)0.76200 (15)0.0285 (9)
C311.2251 (3)0.67363 (11)0.82889 (16)0.0286 (9)
C321.2894 (3)0.70584 (12)0.90163 (17)0.0356 (10)
C331.1850 (4)0.74834 (13)0.92191 (18)0.0433 (11)
C341.1284 (4)0.78681 (13)0.85400 (18)0.0443 (11)
C351.0580 (3)0.75407 (12)0.78232 (17)0.0355 (10)
C361.1257 (3)0.60205 (13)0.89998 (18)0.0390 (10)
C371.0029 (3)0.56049 (13)0.88848 (19)0.0428 (11)
C381.0158 (4)0.51127 (13)0.83900 (19)0.0436 (11)
Li20.9943 (5)0.61331 (19)0.7258 (3)0.0325 (16)
H30.3008000.2171000.7135000.0380*
H40.2007000.1939000.5846000.0400*
H50.2512000.2475000.4851000.0360*
H60.4065000.3253000.5123000.0310*
H7A0.4430000.2378000.8258000.0480*
H7B0.3223000.2860000.8204000.0480*
H8A0.4999000.2809000.9431000.0420*
H8B0.6187000.3030000.8979000.0420*
H9A0.3682000.3655000.9135000.0450*
H9B0.5300000.3764000.9634000.0450*
H100.4018000.4633000.8843000.0350*
H110.3720000.4661000.7504000.0340*
H12A0.4423000.5604000.7341000.0410*
H12B0.3647000.5542000.8056000.0410*
H13A0.5712000.6109000.8436000.0500*
H13B0.6732000.5642000.8177000.0500*
H14A0.7009000.5593000.9524000.0530*
H14B0.5281000.5538000.9438000.0530*
H15A0.6328000.4655000.9683000.0430*
H15B0.7113000.4715000.8970000.0430*
H16A0.6387000.5204000.6824000.0410*
H16B0.4880000.4893000.6461000.0410*
H17A0.7535000.4282000.6716000.0400*
H17B0.7080000.4650000.5951000.0400*
H18A0.4888000.4103000.5581000.0360*
H18B0.6332000.3731000.5643000.0360*
H231.1671000.4998000.5487000.0540*
H241.2096000.4041000.5746000.0580*
H251.1600000.3655000.6862000.0610*
H261.0722000.4208000.7746000.0540*
H27A1.0489000.5791000.5228000.0450*
H27B1.1985000.6030000.5740000.0450*
H28A0.9246000.6550000.5706000.0430*
H28B1.0248000.6731000.5126000.0430*
H29A1.2077000.7036000.6183000.0400*
H29B1.0569000.7360000.6156000.0400*
H301.2503000.7338000.7485000.0340*
H311.3026000.6495000.8152000.0340*
H32A1.3176000.6793000.9450000.0430*
H32B1.3789000.7252000.8947000.0430*
H33A1.2354000.7707000.9668000.0520*
H33B1.1020000.7289000.9365000.0520*
H34A1.2102000.8092000.8431000.0530*
H34B1.0560000.8129000.8675000.0530*
H35A1.0248000.7800000.7387000.0430*
H35B0.9718000.7337000.7917000.0430*
H36A1.1292000.6235000.9480000.0470*
H36B1.2199000.5824000.9044000.0470*
H37A0.9940000.5467000.9398000.0520*
H37B0.9112000.5803000.8656000.0520*
H38A1.1042000.4895000.8620000.0530*
H38B0.9297000.4867000.8353000.0530*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Li10.031 (2)0.023 (2)0.026 (2)0.0011 (19)0.0012 (19)0.0012 (18)
Li20.023 (2)0.030 (3)0.043 (3)0.0028 (19)0.004 (2)0.007 (2)
S10.0297 (4)0.0454 (5)0.0409 (4)0.0019 (3)0.0083 (3)0.0069 (4)
C190.0263 (15)0.0217 (14)0.0308 (15)0.0024 (11)0.0072 (13)0.0023 (12)
N10.0294 (13)0.0362 (14)0.0365 (14)0.0011 (11)0.0019 (12)0.0021 (11)
S20.0284 (4)0.0482 (5)0.0448 (5)0.0078 (4)0.0066 (3)0.0174 (4)
C200.0294 (16)0.0223 (14)0.0319 (15)0.0029 (12)0.0095 (13)0.0038 (12)
N20.0257 (14)0.0322 (14)0.0525 (16)0.0004 (11)0.0077 (12)0.0051 (12)
O10.0307 (10)0.0230 (10)0.0234 (9)0.0075 (8)0.0004 (8)0.0000 (8)
O20.0306 (10)0.0285 (10)0.0243 (10)0.0063 (8)0.0009 (8)0.0010 (8)
O30.0356 (11)0.0274 (11)0.0290 (10)0.0036 (8)0.0074 (8)0.0002 (8)
O40.0286 (10)0.0285 (10)0.0260 (10)0.0002 (8)0.0039 (8)0.0015 (8)
O50.0284 (11)0.0249 (11)0.0589 (14)0.0003 (8)0.0092 (10)0.0079 (10)
O60.0314 (11)0.0268 (11)0.0389 (12)0.0049 (9)0.0017 (9)0.0015 (9)
O70.0344 (11)0.0257 (10)0.0323 (11)0.0100 (8)0.0034 (9)0.0010 (8)
O80.0283 (10)0.0322 (11)0.0372 (11)0.0023 (9)0.0042 (9)0.0099 (9)
C10.0222 (13)0.0181 (13)0.0304 (15)0.0006 (11)0.0008 (11)0.0043 (11)
C20.0233 (14)0.0241 (14)0.0285 (15)0.0017 (11)0.0013 (11)0.0051 (12)
C30.0309 (16)0.0280 (15)0.0361 (17)0.0027 (12)0.0070 (13)0.0016 (13)
C40.0286 (15)0.0262 (15)0.0425 (18)0.0045 (12)0.0014 (13)0.0067 (13)
C50.0276 (15)0.0285 (15)0.0308 (16)0.0027 (12)0.0025 (12)0.0099 (13)
C60.0280 (14)0.0212 (14)0.0266 (14)0.0019 (11)0.0024 (11)0.0024 (11)
C70.0428 (18)0.0431 (19)0.0329 (17)0.0105 (15)0.0075 (14)0.0065 (14)
C80.0405 (17)0.0353 (17)0.0289 (16)0.0019 (14)0.0055 (13)0.0062 (13)
C90.0445 (18)0.0404 (18)0.0292 (16)0.0035 (14)0.0134 (14)0.0071 (14)
C100.0258 (15)0.0305 (15)0.0320 (16)0.0001 (12)0.0084 (12)0.0034 (12)
C110.0206 (13)0.0277 (15)0.0350 (16)0.0023 (11)0.0047 (12)0.0061 (12)
C120.0308 (16)0.0262 (15)0.0456 (18)0.0043 (12)0.0078 (13)0.0001 (13)
C130.0414 (18)0.0341 (17)0.053 (2)0.0134 (14)0.0205 (16)0.0148 (15)
C140.0383 (18)0.058 (2)0.0383 (18)0.0164 (16)0.0157 (15)0.0211 (16)
C150.0270 (15)0.054 (2)0.0261 (15)0.0100 (14)0.0048 (12)0.0055 (14)
C160.0442 (17)0.0245 (15)0.0331 (16)0.0075 (13)0.0070 (13)0.0009 (13)
C170.0374 (17)0.0366 (17)0.0273 (15)0.0096 (13)0.0084 (13)0.0039 (13)
C180.0333 (16)0.0286 (15)0.0270 (15)0.0037 (12)0.0032 (12)0.0021 (12)
C210.0182 (14)0.0283 (16)0.056 (2)0.0053 (12)0.0029 (13)0.0015 (15)
C220.0166 (13)0.0302 (16)0.0508 (19)0.0016 (12)0.0091 (13)0.0141 (15)
C230.0338 (17)0.0408 (19)0.050 (2)0.0024 (14)0.0131 (15)0.0136 (16)
C240.0306 (17)0.0361 (19)0.066 (2)0.0053 (14)0.0180 (16)0.0194 (17)
C250.0298 (17)0.0292 (17)0.084 (3)0.0004 (14)0.0092 (17)0.0116 (19)
C260.0228 (15)0.0294 (17)0.077 (2)0.0030 (13)0.0019 (16)0.0057 (16)
C270.0302 (16)0.0429 (18)0.0351 (17)0.0018 (14)0.0014 (13)0.0073 (14)
C280.0359 (16)0.0385 (17)0.0294 (16)0.0032 (14)0.0000 (13)0.0047 (13)
C290.0355 (16)0.0307 (16)0.0329 (16)0.0037 (13)0.0041 (13)0.0070 (13)
C300.0272 (15)0.0250 (15)0.0336 (16)0.0049 (12)0.0070 (12)0.0026 (12)
C310.0196 (14)0.0244 (14)0.0424 (17)0.0017 (11)0.0079 (12)0.0007 (12)
C320.0322 (16)0.0338 (17)0.0366 (17)0.0004 (13)0.0019 (13)0.0016 (13)
C330.0488 (19)0.0423 (19)0.0364 (18)0.0016 (15)0.0042 (15)0.0052 (14)
C340.051 (2)0.0352 (17)0.0459 (19)0.0084 (15)0.0089 (16)0.0047 (15)
C350.0313 (16)0.0322 (16)0.0410 (18)0.0048 (13)0.0037 (13)0.0046 (13)
C360.0353 (17)0.0415 (18)0.0415 (18)0.0015 (14)0.0114 (14)0.0116 (15)
C370.0397 (18)0.0435 (19)0.048 (2)0.0001 (15)0.0155 (15)0.0151 (16)
C380.0383 (18)0.0340 (18)0.061 (2)0.0017 (14)0.0164 (16)0.0196 (16)
Geometric parameters (Å, º) top
S1—C191.638 (3)C11—H110.9993
S2—C201.636 (3)C12—H12A0.9908
O1—C181.438 (3)C12—H12B0.9903
O1—Li12.052 (4)C13—H13A0.9898
O1—C11.381 (3)C13—H13B0.9906
O2—C71.449 (3)C14—H14A0.9905
O2—Li12.086 (5)C14—H14B0.9899
O2—C21.370 (3)C15—H15A0.9911
O3—C91.429 (3)C15—H15B0.9897
O3—Li11.972 (5)C16—H16A0.9897
O3—C101.427 (3)C16—H16B0.9903
O4—C111.445 (3)C17—H17A0.9898
O4—Li12.068 (5)C17—H17B0.9902
O4—C161.432 (3)C18—H18A0.9899
O5—Li22.079 (5)C18—H18B0.9900
O5—C381.454 (4)C21—C221.396 (4)
O5—C211.356 (4)C21—C261.398 (4)
O6—C221.390 (3)C22—C231.376 (4)
O6—C271.431 (4)C23—C241.399 (4)
O6—Li22.074 (5)C24—C251.379 (5)
O7—C291.435 (3)C25—C261.390 (5)
O7—Li21.965 (5)C27—C281.502 (4)
O7—C301.425 (3)C28—C291.506 (4)
O8—C361.432 (4)C30—C311.519 (4)
O8—C311.453 (3)C30—C351.522 (4)
O8—Li22.073 (5)C31—C321.513 (4)
N1—C191.159 (4)C32—C331.510 (5)
N1—Li11.968 (5)C33—C341.519 (4)
N2—C201.165 (4)C34—C351.518 (4)
N2—Li21.982 (6)C36—C371.504 (4)
C1—C21.400 (4)C37—C381.491 (5)
C1—C61.375 (4)C23—H230.9498
C2—C31.384 (4)C24—H240.9508
C3—C41.392 (4)C25—H250.9500
C4—C51.370 (4)C26—H260.9488
C5—C61.399 (4)C27—H27A0.9888
C7—C81.508 (4)C27—H27B0.9903
C8—C91.501 (4)C28—H28A0.9905
C10—C111.518 (4)C28—H28B0.9903
C10—C151.519 (4)C29—H29A0.9906
C11—C121.523 (4)C29—H29B0.9892
C12—C131.520 (4)C30—H301.0009
C13—C141.524 (4)C31—H310.9996
C14—C151.507 (5)C32—H32A0.9892
C16—C171.513 (4)C32—H32B0.9905
C17—C181.524 (4)C33—H33A0.9910
C3—H30.9505C33—H33B0.9892
C4—H40.9505C34—H34A0.9896
C5—H50.9504C34—H34B0.9903
C6—H60.9498C35—H35A0.9888
C7—H7A0.9906C35—H35B0.9895
C7—H7B0.9906C36—H36A0.9895
C8—H8B0.9899C36—H36B0.9899
C8—H8A0.9908C37—H37A0.9891
C9—H9B0.9898C37—H37B0.9899
C9—H9A0.9896C38—H38A0.9903
C10—H101.0005C38—H38B0.9906
C1—O1—C18117.0 (2)O1—C18—H18A110.21
C1—O1—Li1118.54 (19)C17—C18—H18A110.27
C18—O1—Li1124.5 (2)C17—C18—H18B110.19
C2—O2—C7116.6 (2)S2—C20—N2179.3 (3)
C2—O2—Li1117.63 (18)O5—C21—C22115.5 (3)
C7—O2—Li1124.19 (19)O5—C21—C26125.2 (3)
C9—O3—C10115.5 (2)C22—C21—C26119.2 (3)
C9—O3—Li1128.1 (2)C21—C22—C23121.1 (3)
C10—O3—Li1114.9 (2)O6—C22—C23124.8 (3)
C11—O4—C16114.0 (2)O6—C22—C21114.1 (3)
C11—O4—Li1107.84 (19)C22—C23—C24119.4 (3)
C16—O4—Li1120.22 (18)C23—C24—C25119.7 (3)
C38—O5—Li2124.7 (2)C24—C25—C26121.1 (3)
C21—O5—C38117.6 (2)C21—C26—C25119.3 (3)
C21—O5—Li2117.5 (2)O6—C27—C28109.0 (2)
C27—O6—Li2124.1 (2)C27—C28—C29115.3 (2)
C22—O6—C27118.5 (2)O7—C29—C28107.9 (2)
C22—O6—Li2117.1 (2)C31—C30—C35111.2 (2)
C29—O7—Li2128.5 (2)O7—C30—C31105.9 (2)
C29—O7—C30115.7 (2)O7—C30—C35111.7 (2)
C30—O7—Li2115.2 (2)O8—C31—C30104.7 (2)
C31—O8—C36114.9 (2)O8—C31—C32114.0 (2)
C31—O8—Li2109.5 (2)C30—C31—C32111.2 (2)
C36—O8—Li2122.0 (2)C31—C32—C33112.8 (2)
C19—N1—Li1159.4 (3)C32—C33—C34110.7 (3)
C20—N2—Li2165.4 (3)C33—C34—C35111.4 (3)
O1—C1—C2114.1 (2)C30—C35—C34109.9 (2)
O1—C1—C6125.7 (2)O8—C36—C37108.3 (2)
C2—C1—C6120.2 (2)C36—C37—C38116.5 (3)
C1—C2—C3120.3 (2)O5—C38—C37108.7 (2)
O2—C2—C3125.4 (2)C22—C23—H23120.33
O2—C2—C1114.3 (2)C24—C23—H23120.23
C2—C3—C4119.1 (3)C23—C24—H24120.18
C3—C4—C5120.8 (3)C25—C24—H24120.07
C4—C5—C6120.3 (3)C24—C25—H25119.44
C1—C6—C5119.4 (2)C26—C25—H25119.47
O2—C7—C8108.1 (2)C21—C26—H26120.41
C7—C8—C9114.6 (2)C25—C26—H26120.27
O3—C9—C8108.5 (2)C28—C27—H27A109.86
O3—C10—C11105.8 (2)O6—C27—H27B109.90
O3—C10—C15112.6 (2)H27A—C27—H27B108.29
C11—C10—C15111.4 (2)C28—C27—H27B109.87
O4—C11—C10105.0 (2)O6—C27—H27A109.92
C10—C11—C12110.1 (2)H28A—C28—H28B107.49
O4—C11—C12114.9 (2)C27—C28—H28A108.42
C11—C12—C13112.1 (2)C27—C28—H28B108.42
C12—C13—C14110.3 (2)C29—C28—H28B108.48
C13—C14—C15111.5 (2)C29—C28—H28A108.46
C10—C15—C14111.4 (2)O7—C29—H29B110.17
O4—C16—C17109.3 (2)C28—C29—H29B110.10
C16—C17—C18114.4 (2)O7—C29—H29A110.13
O1—C18—C17107.5 (2)H29A—C29—H29B108.45
S1—C19—N1179.0 (3)C28—C29—H29A110.13
C4—C3—H3120.47C31—C30—H30109.35
C2—C3—H3120.42O7—C30—H30109.30
C5—C4—H4119.62C35—C30—H30109.28
C3—C4—H4119.63C32—C31—H31108.99
C6—C5—H5119.80O8—C31—H31108.96
C4—C5—H5119.88C30—C31—H31108.92
C5—C6—H6120.32C31—C32—H32A109.02
C1—C6—H6120.27C31—C32—H32B109.00
O2—C7—H7A110.07H32A—C32—H32B107.84
H7A—C7—H7B108.34C33—C32—H32B109.01
C8—C7—H7B110.11C33—C32—H32A109.05
O2—C7—H7B110.05C34—C33—H33B109.47
C8—C7—H7A110.13C32—C33—H33B109.49
C7—C8—H8B108.62C32—C33—H33A109.54
H8A—C8—H8B107.61H33A—C33—H33B108.08
C9—C8—H8A108.65C34—C33—H33A109.49
C9—C8—H8B108.56C33—C34—H34A109.33
C7—C8—H8A108.64C33—C34—H34B109.37
H9A—C9—H9B108.39C35—C34—H34A109.38
C8—C9—H9A109.99C35—C34—H34B109.37
C8—C9—H9B110.01H34A—C34—H34B107.91
O3—C9—H9B109.95H35A—C35—H35B108.11
O3—C9—H9A109.96C30—C35—H35A109.69
O3—C10—H10109.04C30—C35—H35B109.65
C15—C10—H10109.00C34—C35—H35B109.72
C11—C10—H10108.91C34—C35—H35A109.71
O4—C11—H11108.86O8—C36—H36B110.07
C12—C11—H11108.91H36A—C36—H36B108.44
C10—C11—H11108.84O8—C36—H36A109.99
C11—C12—H12B109.19C37—C36—H36B109.96
C13—C12—H12B109.20C37—C36—H36A110.02
C13—C12—H12A109.22C38—C37—H37A108.17
C11—C12—H12A109.22C36—C37—H37B108.14
H12A—C12—H12B107.81C36—C37—H37A108.15
C14—C13—H13A109.56C38—C37—H37B108.19
C14—C13—H13B109.57H37A—C37—H37B107.36
C12—C13—H13B109.58O5—C38—H38B109.97
C12—C13—H13A109.63C37—C38—H38B109.87
H13A—C13—H13B108.12O5—C38—H38A110.03
C13—C14—H14B109.31H38A—C38—H38B108.26
C13—C14—H14A109.32C37—C38—H38A109.98
H14A—C14—H14B107.95O4—Li1—N1107.0 (2)
C15—C14—H14A109.37O2—Li1—O385.21 (19)
C15—C14—H14B109.35O2—Li1—O4141.7 (3)
C10—C15—H15A109.34O2—Li1—N1111.0 (2)
H15A—C15—H15B108.01O3—Li1—O480.20 (17)
C14—C15—H15A109.39O3—Li1—N1106.59 (19)
C14—C15—H15B109.33O1—Li1—O3134.2 (3)
C10—C15—H15B109.36O1—Li1—O489.99 (16)
C17—C16—H16B109.75O1—Li1—N1119.0 (2)
C17—C16—H16A109.86O1—Li1—O275.34 (15)
H16A—C16—H16B108.34O5—Li2—O7141.5 (3)
O4—C16—H16B109.83O5—Li2—O889.0 (2)
O4—C16—H16A109.79O5—Li2—O675.72 (18)
C16—C17—H17B108.72O6—Li2—O785.5 (2)
C18—C17—H17B108.64O6—Li2—O8133.4 (3)
H17A—C17—H17B107.55O6—Li2—N2108.3 (3)
C16—C17—H17A108.69O7—Li2—O879.85 (19)
C18—C17—H17A108.64O7—Li2—N2109.8 (2)
O1—C18—H18B110.25O8—Li2—N2118.3 (3)
H18A—C18—H18B108.44O5—Li2—N2107.9 (2)
O1—C1—C2—C3179.7 (3)O5—C21—C22—C23175.9 (3)
O1—C1—C2—O21 (3)O5—C21—C22—O63.3 (4)
O1—C1—C6—C5178.9 (3)O5—C21—C26—C25176.7 (3)
C1—C2—C3—C40.8 (4)C21—C22—C23—C242 (5)
C1—C2—O2—C7169.1 (2)C21—C22—O6—C27176.8 (2)
C2—C1—C6—C50.3 (4)C22—C21—C26—C251.9 (4)
C2—C3—C4—C50.1 (5)C22—C23—C24—C250.1 (5)
C2—O2—C7—C8179.6 (2)C22—O6—C27—C28170.7 (2)
O2—C2—C3—C4180 (3)O6—C22—C23—C24178.9 (3)
O2—C7—C8—C972.9 (3)O6—C27—C28—C2972.7 (3)
C3—C4—C5—C60.5 (4)C23—C24—C25—C260.8 (5)
C4—C5—C6—C10.4 (4)C24—C25—C26—C210.1 (5)
C6—C1—C2—C30.9 (4)C26—C21—C22—C232.9 (5)
C6—C1—C2—O2179.9 (2)C26—C21—C22—O6177.9 (3)
C7—C8—C9—O362.8 (3)C27—C28—C29—O760.8 (3)
C7—O2—C2—C311.7 (4)C27—O6—C22—C232.3 (4)
C8—C9—O3—C10172 (2)C28—C29—O7—C30177.9 (2)
C9—O3—C10—C11157.3 (2)C29—O7—C30—C31149.9 (2)
C9—O3—C10—C1580.8 (3)C29—O7—C30—C3588.9 (3)
O3—C10—C11—C12178.2 (2)O7—C30—C31—C32176.5 (2)
O3—C10—C11—O454 (3)O7—C30—C31—O853 (3)
O3—C10—C15—C14174.8 (2)O7—C30—C35—C34175.2 (2)
C10—C11—C12—C1355.9 (3)C30—C31—C32—C3353.5 (3)
C10—C11—O4—C16175.5 (2)C30—C31—O8—C36173.9 (2)
C11—C10—C15—C1456.2 (3)C31—C30—C35—C3457.1 (3)
C11—C12—C13—C1455.6 (3)C31—C32—C33—C3453.7 (3)
C11—O4—C16—C17155 (2)C31—O8—C36—C37167.1 (2)
O4—C11—C12—C1362.5 (3)O8—C31—C32—C3364.6 (3)
O4—C16—C17—C1882.2 (3)O8—C36—C37—C3882.8 (3)
C12—C13—C14—C1555.2 (3)C32—C33—C34—C3555.8 (4)
C13—C14—C15—C1055.8 (3)C33—C34—C35—C3057.6 (4)
C15—C10—C11—C1255.5 (3)C35—C30—C31—C3254.9 (3)
C15—C10—C11—O468.7 (3)C35—C30—C31—O868.6 (3)
C16—C17—C18—O164.4 (3)C36—C37—C38—O559.6 (4)
C16—O4—C11—C1254.3 (3)C36—O8—C31—C3252.2 (3)
C17—C18—O1—C1177.4 (2)C37—C38—O5—C21166 (3)
C18—O1—C1—C2177.8 (2)C38—O5—C21—C22171.9 (3)
C18—O1—C1—C63.5 (4)C38—O5—C21—C266.8 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···S2i0.952.823.752 (3)166
C7—H7A···S2ii0.992.753.685 (3)158
C9—H9A···S1iii0.992.883.862 (3)173
C12—H12A···S20.992.853.793 (3)159
C27—H27B···S2iv0.992.763.726 (3)164
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y1/2, z+3/2; (iii) x1, y, z; (iv) x+1, y, z.
 

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