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The title compound, C22H29NO4SSi, displays an anomeric effect in the marked shortening of one C-O bond relative to the other in the oxirane ring, concomitantly weakening the C-S bond to the aryl­thio substituent. This correlates with the selective reactivity of nucleophiles at the C atom having the longer C-O bond. The absolute configuration has been determined from anomalous scattering effects.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803014326/bt6296sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803014326/bt6296Isup2.hkl
Contains datablock I

CCDC reference: 217623

Key indicators

  • Single-crystal X-ray study
  • T = 160 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.036
  • wR factor = 0.085
  • Data-to-parameter ratio = 19.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes

REFLT_03 From the CIF: _diffrn_reflns_theta_max 28.91 From the CIF: _reflns_number_total 5239 Count of symmetry unique reflns 3305 Completeness (_total/calc) 158.52% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1934 Fraction of Friedel pairs measured 0.585 Are heavy atom types Z>Si present yes Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF.

Comment top

The title compound, (I), was prepared as one of a series of (arylthio)nitrooxiranes during the development of stereoselective syntheses of protected β-hydroxy-α-amino acids (Adams et al., 1999). The original purpose of the crystal structure determination was to establish the relative stereochemistry of the epoxide ring and the adjacent C atom bearing the phenyl and protected hydroxyl groups, in order to demonstrate the stereoselectivity of the synthetic procedures. In fact, the Si and S atoms in the molecule provide sufficient anomalous scattering to enable the absolute configuration to be determined unambiguously, and it is shown in Fig. 1. It is as expected from the starting material used in the synthesis.

Further interest in the structure arises from the electronic effects of the nitro and arylthio substituents on the bond lengths of the epoxide ring. We have recently shown that a marked asymmetry in the C—O bond lengths of such rings in a number of substituted oxiranes can be ascribed to a generalized anomeric effect, in which a lone pair of electrons on the ring oxygen atom interacts with the antibonding orbital associated with the bond to the heteroatom substituent (here the arylthio group), thus weaking this bond and strengthening the corresponding ring C—O bond (Jackson et al., 2003). This effect is particularly marked with (arylthio)nitrooxiranes, and is believed to be responsible for the selective reaction of these oxiranes with nucleophiles at the carbon atom giving the longer C—O bond.

A search of the Cambridge Structural Database (Version 5.24 plus two updates, June 2003; Allen, 2002) provides known structure for five oxiranes with a nitro substituent (Bowman et al., 1991; Hartshorn et al., 1983; Jackson et al., 1995; Szarek et al., 1988) and five oxiranes with an alkylthio or arylthio substituent (Hewkin et al., 1991; Jackson et al., 1995; Krishnakumar et al., 2002; Valle et al., 1988), two of these structures having both types of substituent. The title compound is thus the third structurally characterized example of an (arylthio)nitrooxirane. In all of these structures, the C—O bond adjacent to the nitro and/or thio substituent is shortened relative to the other C—O bond, though the difference is much more marked in some cases than in others.

Of the three (arylthio)nitroxiranes, the shorter C—O bond of the title compound, adjacent to the nitro and arylthio substituents, has essentially the same length as those in the other two structures [C1—O1 = 1.391 (2) Å, compared with 1.398 (7) and 1.394 (2) Å], but the longer C—O bond is somewhat shorter than the corresponding bond in the other two structures [C2—O1 = 1.448 (2) Å, compared with 1.463 (6) and 1.466 (2) Å]. This fact correlates well with the fact that the title compound is by far the least reactive towards nucleophiles; for example, it requires treatment at 353 K for 6 h with aqueous ammonia, whereas the other compounds react completely within 2 h at room temperature (Jackson, 2003). This is further evidence that the ground-state molecular geometry, resulting from the anomeric effect, influences reactivity, although the larger steric bulk of the substituents in the title compound may also contribute.

Experimental top

The synthesis and spectroscopic characterization of the title compound have been fully described by Adams et al. (1999).

Refinement top

H atoms were placed geometrically and refined with a riding model (including free rotation about C—C bonds), and 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, 2001); cell refinement: local programs; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with atom labels and 50% probability ellipsoids for non-H atoms.
(1'S,2R,3R)-3-(1'-tert-Butyldimethylsilyloxy-1'-phenylmethyl)- 2-(4''-methylphenylthio)-2-nitrooxirane top
Crystal data top
C22H29NO4SSiF(000) = 460
Mr = 431.61Dx = 1.214 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 10.0904 (12) ÅCell parameters from 5503 reflections
b = 8.9428 (11) Åθ = 2.4–28.6°
c = 13.1503 (16) ŵ = 0.21 mm1
β = 95.531 (3)°T = 160 K
V = 1181.1 (2) Å3Block, colourless
Z = 20.51 × 0.38 × 0.35 mm
Data collection top
Bruker SMART 1K CCD
diffractometer
5239 independent reflections
Radiation source: sealed tube4405 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
Detector resolution: 8.192 pixels mm-1θmax = 28.9°, θmin = 2.4°
ω rotation with narrow frames scansh = 913
Absorption correction: multi-scan
(SADABS; Sheldrick, 2002)
k = 1112
Tmin = 0.90, Tmax = 0.93l = 1417
7705 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036H-atom parameters constrained
wR(F2) = 0.085 w = 1/[σ2(Fo2) + (0.0461P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.98(Δ/σ)max = 0.001
5239 reflectionsΔρmax = 0.24 e Å3
268 parametersΔρmin = 0.22 e Å3
1 restraintAbsolute structure: Flack (1983), 2251 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.05 (6)
Crystal data top
C22H29NO4SSiV = 1181.1 (2) Å3
Mr = 431.61Z = 2
Monoclinic, P21Mo Kα radiation
a = 10.0904 (12) ŵ = 0.21 mm1
b = 8.9428 (11) ÅT = 160 K
c = 13.1503 (16) Å0.51 × 0.38 × 0.35 mm
β = 95.531 (3)°
Data collection top
Bruker SMART 1K CCD
diffractometer
5239 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2002)
4405 reflections with I > 2σ(I)
Tmin = 0.90, Tmax = 0.93Rint = 0.020
7705 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.036H-atom parameters constrained
wR(F2) = 0.085Δρmax = 0.24 e Å3
S = 0.98Δρmin = 0.22 e Å3
5239 reflectionsAbsolute structure: Flack (1983), 2251 Friedel pairs
268 parametersAbsolute structure parameter: 0.05 (6)
1 restraint
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.33416 (13)0.41659 (15)0.35992 (10)0.0359 (3)
C10.21246 (18)0.4483 (2)0.30530 (14)0.0326 (4)
C20.28023 (18)0.3071 (2)0.28598 (13)0.0319 (4)
H20.24150.21550.31510.038*
N10.09616 (18)0.4315 (2)0.37214 (14)0.0439 (4)
O20.00947 (16)0.4871 (2)0.34073 (16)0.0679 (5)
O30.11668 (17)0.3605 (2)0.45007 (13)0.0711 (6)
C30.35306 (18)0.2825 (2)0.19186 (14)0.0325 (4)
H30.37720.38120.16310.039*
C40.26396 (17)0.1982 (2)0.11369 (14)0.0318 (4)
C50.24227 (19)0.0459 (2)0.12654 (16)0.0381 (4)
H50.28630.00490.18360.046*
C60.1573 (2)0.0317 (2)0.05692 (16)0.0430 (5)
H60.14270.13540.06670.052*
C70.0935 (2)0.0399 (3)0.02632 (17)0.0421 (5)
H70.03490.01430.07380.051*
C80.1146 (2)0.1905 (3)0.04091 (16)0.0418 (5)
H80.07160.24020.09880.050*
C90.19913 (19)0.2689 (2)0.02950 (15)0.0373 (5)
H90.21270.37280.01980.045*
O40.47070 (12)0.20244 (15)0.22525 (10)0.0372 (3)
Si10.61268 (5)0.23361 (6)0.17355 (4)0.03532 (13)
C100.5900 (3)0.1795 (3)0.03609 (17)0.0582 (6)
H10A0.56370.07420.03020.087*
H10B0.67380.19410.00550.087*
H10C0.52050.24190.00030.087*
C110.6533 (2)0.4356 (3)0.18729 (18)0.0501 (5)
H11A0.61700.48910.12580.075*
H11B0.75020.44840.19650.075*
H11C0.61410.47590.24690.075*
C120.7392 (2)0.1124 (3)0.24831 (15)0.0428 (5)
C130.8753 (2)0.1316 (3)0.2051 (2)0.0647 (7)
H13A0.94160.06770.24330.097*
H13B0.90350.23630.21170.097*
H13C0.86720.10290.13280.097*
C140.7521 (2)0.1612 (3)0.36047 (18)0.0607 (7)
H14A0.66450.15730.38670.091*
H14B0.78660.26360.36590.091*
H14C0.81340.09380.40050.091*
C150.6982 (2)0.0524 (3)0.2397 (2)0.0601 (7)
H15A0.76660.11420.27720.090*
H15B0.68850.08220.16770.090*
H15C0.61320.06630.26880.090*
S10.19777 (5)0.60295 (6)0.22149 (4)0.04069 (13)
C160.23489 (19)0.7470 (2)0.31291 (14)0.0332 (4)
C170.3673 (2)0.7821 (2)0.34352 (17)0.0416 (5)
H170.43700.72930.31570.050*
C180.3967 (2)0.8932 (2)0.41392 (17)0.0447 (5)
H180.48730.91590.43450.054*
C190.2976 (2)0.9733 (2)0.45583 (15)0.0416 (5)
C200.1654 (2)0.9388 (2)0.42300 (16)0.0421 (5)
H200.09590.99370.44960.051*
C210.1336 (2)0.8264 (2)0.35245 (15)0.0383 (5)
H210.04320.80380.33130.046*
C220.3320 (3)1.0933 (3)0.53381 (18)0.0614 (6)
H22A0.41051.06290.57870.092*
H22B0.25681.10860.57460.092*
H22C0.35101.18670.49910.092*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0356 (7)0.0379 (8)0.0328 (7)0.0006 (6)0.0035 (6)0.0036 (6)
C10.0301 (10)0.0345 (10)0.0323 (10)0.0027 (8)0.0016 (8)0.0022 (8)
C20.0311 (10)0.0313 (10)0.0333 (10)0.0021 (8)0.0028 (8)0.0056 (8)
N10.0447 (11)0.0392 (10)0.0489 (11)0.0000 (8)0.0107 (9)0.0060 (9)
O20.0337 (9)0.0737 (12)0.0970 (14)0.0026 (8)0.0109 (8)0.0128 (11)
O30.0731 (12)0.0923 (15)0.0524 (10)0.0186 (11)0.0292 (9)0.0183 (10)
C30.0295 (10)0.0339 (10)0.0343 (10)0.0001 (8)0.0039 (7)0.0081 (8)
C40.0259 (9)0.0365 (11)0.0344 (10)0.0032 (8)0.0091 (7)0.0047 (8)
C50.0354 (11)0.0389 (11)0.0396 (11)0.0010 (9)0.0018 (8)0.0097 (9)
C60.0412 (12)0.0364 (11)0.0521 (13)0.0026 (9)0.0076 (10)0.0001 (10)
C70.0336 (11)0.0505 (13)0.0423 (12)0.0021 (10)0.0041 (9)0.0074 (10)
C80.0370 (11)0.0522 (14)0.0354 (11)0.0105 (10)0.0001 (9)0.0065 (10)
C90.0384 (11)0.0365 (11)0.0375 (10)0.0079 (9)0.0065 (8)0.0080 (9)
O40.0284 (7)0.0455 (8)0.0378 (7)0.0024 (6)0.0033 (5)0.0083 (6)
Si10.0318 (3)0.0439 (3)0.0310 (3)0.0024 (2)0.0065 (2)0.0034 (2)
C100.0607 (15)0.0773 (17)0.0371 (12)0.0078 (13)0.0082 (10)0.0090 (11)
C110.0434 (12)0.0530 (14)0.0551 (13)0.0070 (11)0.0116 (10)0.0008 (11)
C120.0339 (11)0.0537 (12)0.0420 (11)0.0055 (10)0.0094 (8)0.0015 (11)
C130.0355 (13)0.086 (2)0.0746 (17)0.0088 (13)0.0140 (11)0.0026 (16)
C140.0559 (16)0.0828 (19)0.0413 (13)0.0073 (13)0.0066 (11)0.0022 (12)
C150.0580 (16)0.0550 (15)0.0694 (16)0.0091 (12)0.0161 (12)0.0033 (13)
S10.0514 (3)0.0353 (3)0.0332 (2)0.0029 (2)0.0069 (2)0.0039 (2)
C160.0372 (10)0.0293 (9)0.0322 (9)0.0002 (8)0.0016 (8)0.0082 (8)
C170.0350 (11)0.0384 (12)0.0503 (12)0.0001 (9)0.0009 (9)0.0108 (10)
C180.0369 (11)0.0391 (12)0.0548 (13)0.0072 (9)0.0122 (10)0.0109 (10)
C190.0549 (14)0.0333 (10)0.0346 (10)0.0080 (10)0.0062 (9)0.0116 (9)
C200.0468 (12)0.0371 (11)0.0431 (12)0.0005 (10)0.0081 (9)0.0063 (9)
C210.0321 (11)0.0377 (11)0.0439 (11)0.0040 (9)0.0021 (9)0.0074 (9)
C220.0884 (18)0.0447 (13)0.0466 (13)0.0111 (14)0.0164 (11)0.0023 (12)
Geometric parameters (Å, º) top
O1—C11.391 (2)C11—H11A0.980
O1—C21.448 (2)C11—H11B0.980
C1—C21.470 (3)C11—H11C0.980
C1—N11.540 (2)C12—C131.546 (3)
C1—S11.7656 (19)C12—C141.531 (3)
C2—H21.000C12—C151.532 (3)
C2—C31.515 (3)C13—H13A0.980
N1—O21.212 (2)C13—H13B0.980
N1—O31.207 (2)C13—H13C0.980
C3—H31.000C14—H14A0.980
C3—C41.502 (3)C14—H14B0.980
C3—O41.419 (2)C14—H14C0.980
C4—C51.392 (3)C15—H15A0.980
C4—C91.383 (3)C15—H15B0.980
C5—H50.950C15—H15C0.980
C5—C61.380 (3)S1—C161.777 (2)
C6—H60.950C16—C171.394 (3)
C6—C71.373 (3)C16—C211.386 (3)
C7—H70.950C17—H170.950
C7—C81.380 (3)C17—C181.370 (3)
C8—H80.950C18—H180.950
C8—C91.387 (3)C18—C191.386 (3)
C9—H90.950C19—C201.397 (3)
O4—Si11.6673 (13)C19—C221.502 (3)
Si1—C101.864 (2)C20—H200.950
Si1—C111.858 (2)C20—C211.385 (3)
Si1—C121.878 (2)C21—H210.950
C10—H10A0.980C22—H22A0.980
C10—H10B0.980C22—H22B0.980
C10—H10C0.980C22—H22C0.980
C1—O1—C262.31 (12)Si1—C11—H11B109.5
O1—C1—C260.76 (12)Si1—C11—H11C109.5
O1—C1—N1111.64 (15)H11A—C11—H11B109.5
O1—C1—S1119.93 (13)H11A—C11—H11C109.5
C2—C1—N1114.05 (15)H11B—C11—H11C109.5
C2—C1—S1125.27 (14)Si1—C12—C13109.07 (16)
N1—C1—S1114.21 (13)Si1—C12—C14109.29 (16)
O1—C2—C156.93 (11)Si1—C12—C15110.58 (16)
O1—C2—H2115.6C13—C12—C14109.06 (19)
O1—C2—C3117.80 (15)C13—C12—C15108.81 (19)
C1—C2—H2115.6C14—C12—C15110.0 (2)
C1—C2—C3122.46 (16)C12—C13—H13A109.5
H2—C2—C3115.6C12—C13—H13B109.5
C1—N1—O2117.32 (18)C12—C13—H13C109.5
C1—N1—O3117.29 (17)H13A—C13—H13B109.5
O2—N1—O3125.35 (19)H13A—C13—H13C109.5
C2—C3—H3109.6H13B—C13—H13C109.5
C2—C3—C4109.08 (15)C12—C14—H14A109.5
C2—C3—O4106.13 (14)C12—C14—H14B109.5
H3—C3—C4109.6C12—C14—H14C109.5
H3—C3—O4109.6H14A—C14—H14B109.5
C4—C3—O4112.74 (15)H14A—C14—H14C109.5
C3—C4—C5119.90 (18)H14B—C14—H14C109.5
C3—C4—C9121.62 (17)C12—C15—H15A109.5
C5—C4—C9118.5 (2)C12—C15—H15B109.5
C4—C5—H5119.8C12—C15—H15C109.5
C4—C5—C6120.4 (2)H15A—C15—H15B109.5
H5—C5—C6119.8H15A—C15—H15C109.5
C5—C6—H6119.7H15B—C15—H15C109.5
C5—C6—C7120.6 (2)C1—S1—C1698.39 (8)
H6—C6—C7119.7S1—C16—C17119.50 (15)
C6—C7—H7120.1S1—C16—C21120.67 (15)
C6—C7—C8119.9 (2)C17—C16—C21119.83 (19)
H7—C7—C8120.1C16—C17—H17120.1
C7—C8—H8120.2C16—C17—C18119.8 (2)
C7—C8—C9119.6 (2)H17—C17—C18120.1
H8—C8—C9120.2C17—C18—H18119.1
C4—C9—C8121.07 (19)C17—C18—C19121.73 (19)
C4—C9—H9119.5H18—C18—C19119.1
C8—C9—H9119.5C18—C19—C20117.84 (19)
C3—O4—Si1121.04 (11)C18—C19—C22120.9 (2)
O4—Si1—C10108.77 (10)C20—C19—C22121.3 (2)
O4—Si1—C11108.25 (9)C19—C20—H20119.3
O4—Si1—C12104.91 (8)C19—C20—C21121.3 (2)
C10—Si1—C11110.61 (12)H20—C20—C21119.3
C10—Si1—C12111.83 (11)C16—C21—C20119.46 (19)
C11—Si1—C12112.20 (11)C16—C21—H21120.3
Si1—C10—H10A109.5C20—C21—H21120.3
Si1—C10—H10B109.5C19—C22—H22A109.5
Si1—C10—H10C109.5C19—C22—H22B109.5
H10A—C10—H10B109.5C19—C22—H22C109.5
H10A—C10—H10C109.5H22A—C22—H22B109.5
H10B—C10—H10C109.5H22A—C22—H22C109.5
Si1—C11—H11A109.5H22B—C22—H22C109.5
C2—O1—C1—N1106.29 (16)C2—C3—O4—Si1144.35 (12)
C2—O1—C1—S1116.18 (16)C4—C3—O4—Si196.30 (16)
C1—O1—C2—C3112.38 (18)C3—O4—Si1—C1063.96 (16)
O1—C1—C2—C3104.20 (19)C3—O4—Si1—C1156.28 (16)
N1—C1—C2—O1102.30 (17)C3—O4—Si1—C12176.25 (13)
N1—C1—C2—C3153.50 (17)O4—Si1—C12—C13179.23 (16)
S1—C1—C2—O1107.73 (17)O4—Si1—C12—C1461.63 (18)
S1—C1—C2—C33.5 (3)O4—Si1—C12—C1559.61 (16)
O1—C1—N1—O2164.08 (18)C10—Si1—C12—C1361.5 (2)
O1—C1—N1—O317.9 (2)C10—Si1—C12—C14179.36 (17)
C2—C1—N1—O2129.39 (19)C10—Si1—C12—C1558.13 (18)
C2—C1—N1—O348.6 (2)C11—Si1—C12—C1363.47 (19)
S1—C1—N1—O224.0 (2)C11—Si1—C12—C1455.67 (19)
S1—C1—N1—O3158.04 (17)C11—Si1—C12—C15176.91 (15)
O1—C2—C3—C4165.07 (15)O1—C1—S1—C1662.77 (16)
O1—C2—C3—O473.21 (18)C2—C1—S1—C16136.33 (17)
C1—C2—C3—C498.4 (2)N1—C1—S1—C1673.74 (14)
C1—C2—C3—O4139.90 (17)C1—S1—C16—C1783.59 (16)
C2—C3—C4—C574.9 (2)C1—S1—C16—C2197.63 (16)
C2—C3—C4—C9103.40 (19)S1—C16—C17—C18179.95 (15)
O4—C3—C4—C542.8 (2)C21—C16—C17—C181.2 (3)
O4—C3—C4—C9138.97 (17)C16—C17—C18—C190.3 (3)
C3—C4—C5—C6177.91 (17)C17—C18—C19—C200.9 (3)
C9—C4—C5—C60.4 (3)C17—C18—C19—C22179.26 (19)
C4—C5—C6—C70.4 (3)C18—C19—C20—C211.3 (3)
C5—C6—C7—C80.2 (3)C22—C19—C20—C21178.82 (19)
C6—C7—C8—C90.8 (3)C19—C20—C21—C160.5 (3)
C3—C4—C9—C8178.46 (17)S1—C16—C21—C20179.50 (15)
C5—C4—C9—C80.2 (3)C17—C16—C21—C200.7 (3)
C7—C8—C9—C40.8 (3)

Experimental details

Crystal data
Chemical formulaC22H29NO4SSi
Mr431.61
Crystal system, space groupMonoclinic, P21
Temperature (K)160
a, b, c (Å)10.0904 (12), 8.9428 (11), 13.1503 (16)
β (°) 95.531 (3)
V3)1181.1 (2)
Z2
Radiation typeMo Kα
µ (mm1)0.21
Crystal size (mm)0.51 × 0.38 × 0.35
Data collection
DiffractometerBruker SMART 1K CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2002)
Tmin, Tmax0.90, 0.93
No. of measured, independent and
observed [I > 2σ(I)] reflections
7705, 5239, 4405
Rint0.020
(sin θ/λ)max1)0.680
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.085, 0.98
No. of reflections5239
No. of parameters268
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.24, 0.22
Absolute structureFlack (1983), 2251 Friedel pairs
Absolute structure parameter0.05 (6)

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXTL (Sheldrick, 2001), SHELXTL and local programs.

Selected geometric parameters (Å, º) top
O1—C11.391 (2)C2—C31.515 (3)
O1—C21.448 (2)N1—O21.212 (2)
C1—C21.470 (3)N1—O31.207 (2)
C1—N11.540 (2)S1—C161.777 (2)
C1—S11.7656 (19)
C1—O1—C262.31 (12)O1—C2—C156.93 (11)
O1—C1—C260.76 (12)O1—C2—C3117.80 (15)
O1—C1—N1111.64 (15)C1—C2—C3122.46 (16)
O1—C1—S1119.93 (13)C1—N1—O2117.32 (18)
C2—C1—N1114.05 (15)C1—N1—O3117.29 (17)
C2—C1—S1125.27 (14)O2—N1—O3125.35 (19)
N1—C1—S1114.21 (13)C1—S1—C1698.39 (8)
 

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