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The structure of the title ozonide, C20H22O3S, produced without the use of ozone, has been defined at 123 (1) K. In the triclinic crystal, the mol­ecule has symmetry close to Cs, and its ozonide and 1,4-oxa­thiane rings have envelope and chair conformations, respectively. The ozonide unit has an O-O bond length of 1.4721 (12) Å and a C-O-O-C torsion angle of -1.45 (12)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100013147/fr1303sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100013147/fr1303Isup2.hkl
Contains datablock I

CCDC reference: 156185

Comment top

Conventionally, ozonides are prepared by the action of molecular ozone, O3, on alkenes (March, 1992). We have described the facile high-yield formation of a stable ozonide, (I), by air (or neat O2) oxidation of 2,2,4,4-tetramethyl-1,5-diphenyl-8-oxa-3-thia-6,7-diazabicyclo[3.2.1]octane, (II), in benzene solution at room temperature (Cuthbertson et al., 1975). This communication gives the first structural details concerning this novel ozonide, (I), and reports the outcome of a literature survey of ozonides undertaken to establish any relationship between the O—O bond length and the endocyclic C—O—O—C torsion angle. \sch

The molecule of (I) has symmetry close to Cs, with a non-crystallographic mirror plane passing through O3 and S1 and bisecting the ozonide O—O bond, as illustrated in Fig. 1. The symmetry may also be appreciated by consideration of the following pairs of corresponding torsion angles: O1—O2—C14—O3 and O2—O1—C7—O3, −20.8 (1) and 23.0 (1)°, respectively, O3—C7—C8—S1 and O3—C14—C11—S1, −60.5 (1) and 60.7 (1)°, respectively, and O1—C7—C1—C2 and O2—C14—C15—C16, 36.3 (2) and −33.5 (2)°, respectively. Selected structural parameters, including other torsion angles, are given in Table 1. The close approach to Cs symmetry in (I) also extends to the bond lengths (Table 1) and, interestingly, the marked asymmetry often found for the C—O bonds involving the peroxy moiety of the ozonide (Tzou et al., 1996) is not present in (I), since the O1—C7 and O2—C14 bond lengths [1.4509 (15) and 1.4517 (15) Å, respectively] do not differ significantly.

The ozonide ring has an envelope conformation, with O3 displaced by −0.513 (2) Å from the mean plane of C7, O1, O2 and C14, which are coplanar (r.m.s. deviation 0.007 Å). The six-membered 1,4-oxathiane ring has a chair conformation, with C7, C8, C11 and C14 coplanar (r.m.s. deviation 0.000 Å) and S1 and O3 displaced by −0.684 (2) and 0.807 (1) Å, respectively, from this mean plane. Comparison of the angle α subtended between the planes defined by C8, S1 and C11 and C7, C8, C11 and C14 [37.27 (5)°] with the corresponding α parameter for a system unconstrained by bridging such as trans-2,3-dichloro-1,4-oxathiane (46.1°; Desseyn et al., 1972) indicates the presence of an inverse reflex effect (Jefford et al., 1970). Thus `pinching' brought about by the syn-axial placement of the O—O bridge in (I) results in a displacement of S1 towards the plane described by the four C atoms, with a corresponding decrease in the value of α. The corresponding value of α in (II), reflecting the presence of its two-atom hydrazo-bridge, is 36.2° (Cuthbertson et al., 1975).

Searching the Cambridge Structural Database (CSD; Allen & Kennard 1993) for the five-membered ozone substructure [C7, O1, O2, C14 and O3 in (I)] identifies 47 crystallographically unique fragments. The O—O bond length in (I) of 1.4721 (12) Å is indistinguishable from the average value for these 47 ozonides of 1.473 (11) Å and may be compared with the value of 1.481 (10) Å for the corresponding bond in 3,4aβ,5,7,8,8a-hexahydro-3,3-dimethyl-7β,8aβ-diphenyl-5α,7α-epidioxy- pyrano[3,4-e]-1,2,4-trioxane at 295 K (Buckleton et al., 1995), the respective C—O—O—C torsion angles being −1.45 (12) and 7.4 (8)°. The majority of the O—O bond lengths lie in the range ~1.46–1.50 Å, with a wide range of C—O—O—C torsion angles spanning 0° to ~50°.

Seeking to establish whether or not a correlation exists between the O—O bond length and the C—O—O—C torsion angle in the ozone ring, a scattergram of O—O distance versus C—O—O—C torsion angle was generated. No apparent general correlation between these two parameters was revealed, with 27 cases having a torsion angle in a narrow range of 0 to ±10° and with O—O bond lengths spanning ~1.445–1.497 Å. Interestingly, a relatively isolated group of ten cases with torsion angles in the range ±40–50° displayed a narrower range of O—O bond lengths [~ 1.465–1.475 Å], possibly reflecting a reduced range of strain energy associated with relaxation of the endocyclic C—O—O—C torsion angle.

A packing diagram for (I) is shown in Fig. 2. There are no formal hydrogen bonds present in the structure, although the packing diagram reveals both a π-π ring-stacking interaction and a C—H···π edge-to-face interaction with a centrosymmetrically related molecule; contact distances are given in Table 2.

Experimental top

Compound (I) was prepared as described previously by Cuthbertson et al. (1975) and was recrystallized from ethanol, giving colourless needles [m.p. 455–458 K (decomp.)].

Refinement top

H atoms were placed geometrically with C—H = 0.95 Å (0.98 Å for methyl H) and refined with a riding model (including free rotation about C—C bonds for methyl groups), with Uiso constrained to be 1.2 (1.5 for methyl groups) times Ueq of the carrier atom.

Computing details top

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

Figures top
[Figure 1] Fig. 1. A molecular view of (I) with the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
[Figure 2] Fig. 2. The molecular packing of (I) in the triclinic crystal, viewed along a.
2,2,4,4-Tetramethyl-1,5-diphenyl-6,7,8-trioxa-3-thiabicyclo[3.2.1]octane top
Crystal data top
C20H22O3SF(000) = 364
Mr = 342.44Dx = 1.330 Mg m3
Triclinic, P1Melting point = 455–458 K
a = 6.0507 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.6570 (9) ÅCell parameters from 5133 reflections
c = 15.4541 (14) Åθ = 2.2–29.1°
α = 82.093 (8)°µ = 0.20 mm1
β = 78.738 (6)°T = 123 K
γ = 75.898 (5)°Prism, colourless
V = 855.08 (13) Å30.40 × 0.25 × 0.20 mm
Z = 2
Data collection top
Bruker 1K CCD area-detector
diffractometer
2844 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.015
Graphite monochromatorθmax = 26.4°, θmin = 2.2°
Detector resolution: 8.192 pixels mm-1h = 77
narrow frame ω scansk = 1212
7324 measured reflectionsl = 1819
3459 independent reflections
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)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.07P)2]
where P = (Fo2 + 2Fc2)/3
3459 reflections(Δ/σ)max < 0.001
221 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = 0.26 e Å3
Crystal data top
C20H22O3Sγ = 75.898 (5)°
Mr = 342.44V = 855.08 (13) Å3
Triclinic, P1Z = 2
a = 6.0507 (5) ÅMo Kα radiation
b = 9.6570 (9) ŵ = 0.20 mm1
c = 15.4541 (14) ÅT = 123 K
α = 82.093 (8)°0.40 × 0.25 × 0.20 mm
β = 78.738 (6)°
Data collection top
Bruker 1K CCD area-detector
diffractometer
2844 reflections with I > 2σ(I)
7324 measured reflectionsRint = 0.015
3459 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0330 restraints
wR(F2) = 0.097H-atom parameters constrained
S = 1.02Δρmax = 0.31 e Å3
3459 reflectionsΔρmin = 0.26 e Å3
221 parameters
Special details top

Experimental. The data collection nominally covered a sphere of reciprocal space by a combination of three sets of exposures; each set had a different ϕ angle for the crystal, 0, 120 and 240°, repectively. Each exposure covered 0.3° in ω with a 30 s correlated frame time. A total of 600 frames were accumalated in each ω sweep. The crystal to detector distance was 4.935 cm. Coverage of the unique set was 87.2% to 29.13° in θ (0.73 Å) and 98.8% complete to 26.37° in θ (0.80 Å). Crystal decay was monitored by repeating the initial 50 frames at the end of data collection and analyzing the duplicate reflections; a further 50 frames of data were collected at positive 2θ to improve cell refinement statistics. The data were truncated to 0.80 Å for structure refinement. Area detector scaling and absorption corrections were performed by SADABS (Bruker, 1997). This correction was used to scale the frames of data and to correct for absorption of the primary beam by the crystal support using the method of Blessing (1995). A correction for absorption of the primary beam by the crystal was not applied and as such no transmission factors are quoted.

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
S10.18724 (6)0.36650 (4)0.30752 (2)0.02190 (12)
O10.13998 (16)0.17180 (10)0.17777 (6)0.0220 (2)
O20.13827 (15)0.08330 (10)0.26333 (6)0.0203 (2)
O30.50154 (15)0.11321 (10)0.21065 (6)0.0178 (2)
C10.4563 (2)0.20528 (14)0.06263 (9)0.0202 (3)
C20.3107 (3)0.23670 (16)0.00094 (10)0.0258 (3)
H2A0.14850.26870.01650.031*
C30.4030 (3)0.22118 (16)0.08905 (10)0.0299 (4)
H3A0.30350.24210.13190.036*
C40.6387 (3)0.17550 (16)0.11550 (10)0.0294 (4)
H4A0.70080.16450.17620.035*
C50.7845 (3)0.14577 (16)0.05266 (10)0.0277 (3)
H5A0.94670.11500.07050.033*
C60.6935 (2)0.16094 (15)0.03564 (9)0.0232 (3)
H6A0.79370.14090.07820.028*
C70.3572 (2)0.21752 (14)0.15981 (9)0.0192 (3)
C80.3241 (2)0.36882 (14)0.19027 (9)0.0203 (3)
C90.1533 (3)0.48171 (15)0.14157 (10)0.0253 (3)
H9A0.22230.49680.07910.038*
H9B0.11760.57220.16880.038*
H9C0.01070.44830.14570.038*
C100.5572 (2)0.41249 (15)0.17563 (10)0.0239 (3)
H10A0.61200.42950.11190.036*
H10B0.67030.33550.20170.036*
H10C0.53830.50040.20390.036*
C110.3240 (2)0.19025 (14)0.35739 (9)0.0196 (3)
C120.5561 (2)0.19121 (16)0.38289 (10)0.0248 (3)
H12A0.61490.09910.41520.037*
H12B0.53460.26870.42060.037*
H12C0.66730.20640.32910.037*
C130.1521 (2)0.16152 (16)0.44105 (9)0.0246 (3)
H13A0.21770.07140.47380.037*
H13B0.00750.15440.42430.037*
H13C0.12130.24040.47850.037*
C140.3570 (2)0.07823 (14)0.29035 (9)0.0179 (3)
C150.4540 (2)0.07564 (14)0.32400 (8)0.0186 (3)
C160.3067 (2)0.16325 (15)0.36784 (9)0.0216 (3)
H16A0.14490.12480.38030.026*
C170.3953 (3)0.30634 (16)0.39332 (10)0.0267 (3)
H17A0.29380.36570.42260.032*
C180.6315 (3)0.36314 (16)0.37616 (10)0.0272 (3)
H18A0.69190.46130.39330.033*
C190.7794 (3)0.27569 (16)0.33375 (10)0.0257 (3)
H19A0.94150.31400.32260.031*
C200.6915 (2)0.13251 (15)0.30757 (9)0.0218 (3)
H20A0.79340.07330.27840.026*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0225 (2)0.01777 (19)0.0229 (2)0.00087 (13)0.00198 (14)0.00263 (13)
O10.0207 (5)0.0250 (5)0.0215 (5)0.0090 (4)0.0080 (4)0.0076 (4)
O20.0182 (5)0.0243 (5)0.0185 (5)0.0068 (4)0.0055 (4)0.0047 (4)
O30.0161 (5)0.0187 (5)0.0174 (5)0.0028 (4)0.0037 (4)0.0016 (4)
C10.0249 (7)0.0150 (7)0.0212 (7)0.0058 (5)0.0054 (6)0.0013 (5)
C20.0277 (8)0.0251 (8)0.0267 (8)0.0082 (6)0.0097 (6)0.0015 (6)
C30.0433 (10)0.0273 (8)0.0242 (8)0.0142 (7)0.0135 (7)0.0033 (6)
C40.0473 (10)0.0221 (8)0.0203 (7)0.0133 (7)0.0029 (7)0.0015 (6)
C50.0324 (8)0.0206 (8)0.0271 (8)0.0045 (6)0.0001 (6)0.0014 (6)
C60.0268 (8)0.0205 (7)0.0211 (7)0.0045 (6)0.0047 (6)0.0012 (6)
C70.0168 (7)0.0190 (7)0.0221 (7)0.0042 (5)0.0061 (5)0.0018 (5)
C80.0199 (7)0.0190 (7)0.0212 (7)0.0039 (5)0.0040 (5)0.0007 (5)
C90.0237 (7)0.0204 (7)0.0300 (8)0.0032 (6)0.0061 (6)0.0026 (6)
C100.0238 (8)0.0212 (7)0.0277 (8)0.0084 (6)0.0037 (6)0.0007 (6)
C110.0193 (7)0.0193 (7)0.0194 (7)0.0021 (5)0.0048 (5)0.0008 (5)
C120.0262 (8)0.0258 (8)0.0248 (7)0.0054 (6)0.0089 (6)0.0042 (6)
C130.0257 (8)0.0262 (8)0.0199 (7)0.0038 (6)0.0022 (6)0.0015 (6)
C140.0147 (6)0.0208 (7)0.0181 (7)0.0043 (5)0.0028 (5)0.0007 (5)
C150.0226 (7)0.0186 (7)0.0151 (6)0.0031 (5)0.0057 (5)0.0024 (5)
C160.0219 (7)0.0231 (7)0.0190 (7)0.0042 (6)0.0033 (6)0.0007 (6)
C170.0331 (8)0.0233 (8)0.0243 (8)0.0092 (6)0.0049 (6)0.0007 (6)
C180.0363 (9)0.0185 (7)0.0261 (8)0.0012 (6)0.0109 (7)0.0006 (6)
C190.0244 (8)0.0259 (8)0.0254 (8)0.0014 (6)0.0077 (6)0.0054 (6)
C200.0212 (7)0.0225 (7)0.0218 (7)0.0037 (6)0.0051 (6)0.0026 (6)
Geometric parameters (Å, º) top
S1—C111.8378 (14)C18—C191.390 (2)
S1—C81.8389 (14)C19—C201.389 (2)
O1—C71.4509 (15)C2—H2A0.9500
O1—O21.4721 (12)C3—H3A0.9500
O2—C141.4517 (15)C4—H4A0.9500
O3—C141.4158 (15)C5—H5A0.9500
O3—C71.4202 (15)C6—H6A0.9500
C1—C61.390 (2)C9—H9A0.9800
C1—C21.3999 (19)C9—H9B0.9800
C1—C71.5139 (19)C9—H9C0.9800
C2—C31.381 (2)C10—H10A0.9800
C3—C41.382 (2)C10—H10B0.9800
C4—C51.392 (2)C10—H10C0.9800
C5—C61.382 (2)C12—H12A0.9800
C7—C81.5513 (19)C12—H12B0.9800
C8—C91.5338 (18)C12—H12C0.9800
C8—C101.5355 (18)C13—H13A0.9800
C11—C121.5338 (19)C13—H13B0.9800
C11—C131.5317 (19)C13—H13C0.9800
C11—C141.5511 (19)C16—H16A0.9500
C14—C151.5181 (18)C17—H17A0.9500
C15—C161.3940 (19)C18—H18A0.9500
C15—C201.3936 (19)C19—H19A0.9500
C16—C171.387 (2)C20—H20A0.9500
C17—C181.387 (2)
C1···C4i3.813 (2)H3A···C19i3.22
C2···C5i3.830 (2)H4A···C16i2.97
C3···C6i3.829 (2)
C11—S1—C8104.21 (6)C3—C2—H2A120.0
C7—O1—O2105.75 (8)C1—C2—H2A120.0
C14—O2—O1105.96 (8)C2—C3—H3A119.6
C14—O3—C7106.04 (9)C4—C3—H3A119.6
C6—C1—C2119.21 (13)C3—C4—H4A120.2
C6—C1—C7120.23 (12)C5—C4—H4A120.2
C2—C1—C7120.55 (13)C6—C5—H5A120.0
C3—C2—C1119.91 (14)C4—C5—H5A120.0
C2—C3—C4120.70 (14)C5—C6—H6A119.7
C3—C4—C5119.60 (14)C1—C6—H6A119.7
C6—C5—C4120.05 (15)C8—C9—H9A109.5
C5—C6—C1120.51 (13)C8—C9—H9B109.5
O3—C7—O1103.96 (10)H9A—C9—H9B109.5
O3—C7—C1108.39 (11)C8—C9—H9C109.5
O1—C7—C1107.90 (10)H9A—C9—H9C109.5
O3—C7—C8110.57 (10)H9B—C9—H9C109.5
O1—C7—C8110.89 (11)C8—C10—H10A109.5
C1—C7—C8114.56 (11)C8—C10—H10B109.5
C9—C8—C10109.83 (11)H10A—C10—H10B109.5
C9—C8—C7111.65 (11)C8—C10—H10C109.5
C10—C8—C7110.38 (11)H10A—C10—H10C109.5
C9—C8—S1104.71 (10)H10B—C10—H10C109.5
C10—C8—S1111.59 (10)C11—C12—H12A109.5
C7—C8—S1108.56 (9)C11—C12—H12B109.5
C13—C11—C12109.64 (11)H12A—C12—H12B109.5
C13—C11—C14111.70 (11)C11—C12—H12C109.5
C12—C11—C14110.58 (11)H12A—C12—H12C109.5
C13—C11—S1104.48 (9)H12B—C12—H12C109.5
C12—C11—S1111.94 (9)C11—C13—H13A109.5
C14—C11—S1108.36 (9)C11—C13—H13B109.5
O3—C14—O2104.25 (10)H13A—C13—H13B109.5
O3—C14—C15108.28 (11)C11—C13—H13C109.5
O2—C14—C15107.81 (10)H13A—C13—H13C109.5
O3—C14—C11110.85 (10)H13B—C13—H13C109.5
O2—C14—C11110.08 (10)C17—C16—H16A119.9
C15—C14—C11114.99 (11)C15—C16—H16A119.9
C16—C15—C20119.36 (12)C16—C17—H17A119.9
C16—C15—C14120.57 (12)C18—C17—H17A119.9
C20—C15—C14120.00 (12)C17—C18—H18A120.2
C17—C16—C15120.28 (13)C19—C18—H18A120.2
C16—C17—C18120.28 (13)C18—C19—H19A119.8
C17—C18—C19119.65 (13)C20—C19—H19A119.8
C18—C19—C20120.31 (14)C19—C20—H20A120.0
C19—C20—C15120.10 (13)C15—C20—H20A120.0
C7—O1—O2—C141.45 (12)C8—S1—C11—C13157.84 (9)
C6—C1—C2—C31.1 (2)C8—S1—C11—C1283.58 (11)
C7—C1—C2—C3178.18 (13)C8—S1—C11—C1438.62 (10)
C1—C2—C3—C40.3 (2)C7—O3—C14—O236.19 (12)
C2—C3—C4—C50.4 (2)C7—O3—C14—C15150.78 (10)
C3—C4—C5—C60.5 (2)C7—O3—C14—C1182.22 (12)
C4—C5—C6—C10.3 (2)O1—O2—C14—O320.78 (12)
C2—C1—C6—C51.0 (2)O1—O2—C14—C15135.71 (10)
C7—C1—C6—C5178.22 (12)O1—O2—C14—C1198.14 (11)
C14—O3—C7—O137.10 (12)C13—C11—C14—O3175.24 (10)
C14—O3—C7—C1151.71 (10)C12—C11—C14—O362.35 (14)
C14—O3—C7—C881.96 (12)S1—C11—C14—O360.68 (12)
O2—O1—C7—O323.04 (12)C13—C11—C14—O260.43 (14)
O2—O1—C7—C1138.00 (10)C12—C11—C14—O2177.16 (10)
O2—O1—C7—C895.80 (11)S1—C11—C14—O254.13 (12)
C6—C1—C7—O330.96 (16)C13—C11—C14—C1561.54 (15)
C2—C1—C7—O3148.27 (12)C12—C11—C14—C1560.86 (14)
C6—C1—C7—O1142.96 (12)S1—C11—C14—C15176.10 (9)
C2—C1—C7—O136.27 (16)O3—C14—C15—C16145.74 (12)
C6—C1—C7—C893.02 (15)O2—C14—C15—C1633.50 (16)
C2—C1—C7—C887.75 (15)C11—C14—C15—C1689.69 (15)
O3—C7—C8—C9175.41 (10)O3—C14—C15—C2031.27 (16)
O1—C7—C8—C960.64 (14)O2—C14—C15—C20143.50 (12)
C1—C7—C8—C961.78 (15)C11—C14—C15—C2093.30 (15)
O3—C7—C8—C1062.12 (14)C20—C15—C16—C171.2 (2)
O1—C7—C8—C10176.89 (10)C14—C15—C16—C17175.79 (12)
C1—C7—C8—C1060.69 (15)C15—C16—C17—C180.6 (2)
O3—C7—C8—S160.49 (12)C16—C17—C18—C190.4 (2)
O1—C7—C8—S154.29 (12)C17—C18—C19—C200.8 (2)
C1—C7—C8—S1176.70 (9)C18—C19—C20—C150.2 (2)
C11—S1—C8—C9158.09 (9)C16—C15—C20—C190.8 (2)
C11—S1—C8—C1083.15 (11)C14—C15—C20—C19176.22 (12)
C11—S1—C8—C738.72 (10)
Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC20H22O3S
Mr342.44
Crystal system, space groupTriclinic, P1
Temperature (K)123
a, b, c (Å)6.0507 (5), 9.6570 (9), 15.4541 (14)
α, β, γ (°)82.093 (8), 78.738 (6), 75.898 (5)
V3)855.08 (13)
Z2
Radiation typeMo Kα
µ (mm1)0.20
Crystal size (mm)0.40 × 0.25 × 0.20
Data collection
DiffractometerBruker 1K CCD area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
7324, 3459, 2844
Rint0.015
(sin θ/λ)max1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.097, 1.02
No. of reflections3459
No. of parameters221
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.31, 0.26

Computer programs: SMART (Bruker, 1997), SMART and SAINT (Bruker, 1997), SAINT, SHELXTL (Sheldrick, 1997), SHELXTL.

Selected geometric parameters (Å, º) top
S1—C111.8378 (14)O3—C71.4202 (15)
S1—C81.8389 (14)C1—C71.5139 (19)
O1—C71.4509 (15)C7—C81.5513 (19)
O1—O21.4721 (12)C11—C141.5511 (19)
O2—C141.4517 (15)C14—C151.5181 (18)
O3—C141.4158 (15)
C1···C4i3.813 (2)H3A···C19i3.22
C2···C5i3.830 (2)H4A···C16i2.97
C3···C6i3.829 (2)
C11—S1—C8104.21 (6)O1—C7—C8110.89 (11)
C7—O1—O2105.75 (8)C7—C8—S1108.56 (9)
C14—O2—O1105.96 (8)C14—C11—S1108.36 (9)
C14—O3—C7106.04 (9)O3—C14—O2104.25 (10)
O3—C7—O1103.96 (10)O3—C14—C11110.85 (10)
O3—C7—C8110.57 (10)O2—C14—C11110.08 (10)
C7—O1—O2—C141.45 (12)O1—O2—C14—O320.78 (12)
O2—O1—C7—O323.04 (12)S1—C11—C14—O360.68 (12)
C2—C1—C7—O136.27 (16)O2—C14—C15—C1633.50 (16)
O3—C7—C8—S160.49 (12)
Symmetry code: (i) x+1, y, z.
 

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