supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportsimilar papers Open access

Acta Cryst. (2008). E64, o1913    [ doi:10.1107/S1600536808028225 ]

(R)-N-{2-tert-Butyl-2-[(R)-tert-butylsulfonamido]ethylidene}-tert-butanesulfonamide

Y. Hu, X.-X. Sun and C.-B. Fan

Abstract top

The title compound, C14H30N2O2S2, is the product of the monoaddition reaction of tert-butyl magnesium chloride with bis-[(R)-N-tert-butanesulfinyl]ethanediimine. There are two almost identical molecules in the asymmetric unit, the molecular conformation of which is stabilized by an intramolecular N-H...N hydrogen bond.

Comment top

The title compound is an important imtermediate for the synthesis of unsymmetrically disubstituted 1,2-diamines and C2-symmetric vicinal diamines. There are two almost identical molecules in the asymmetric unit whose molecular conformation is stabilized by an intramolecular N—H···N hydrogen bond.

Related literature top

For related literature, see: Sun et al. (2005). Alexakis et al. (2000); Alvaro et al. (1997); Bambridge et al. (1994); Lucet et al. (1998); Roland & Mangeney (2000); Roland et al. (1999).

Experimental top

R-1-Amino-1-tert-butyl-N,N'-bis[(R)- N-tert-butanesulfinyl]-2-iminoethane was prepared from bis-[(R)-N-tert-butanesulfinyl]ethanediimine (264 mg, 1.00 mmol). The solution of bis-[(R)-N-tert-butanesulfinyl]ethanediimine was cooled to 195 K under a argon atmosphere. 3 mol/l t-BuMgCl in diethyl ether (0.5 ml) was added slowly to the solution and stirred for 3–5 h. The combined organic layers were dried over magnesium sulfate, filtered and concentrated.

Single crystals suitable for X-ray diffraction analysis were obtained by slow diffusion of diethyl ether into the solution.

1HNMR (300 MHz, CDCl3, TMS): δ 1.03 (s, 9H, –3CH3), 1.22 (s, 9H, –3CH3), 1.26 (s, 9H, –3CH3), 3.98 (m, 1H, –NH), 4.84 (d, 1H, J = 5.6 Hz, –CH), 8.28 (d, 1H, J = 2.9 Hz, –CH); 13C NMR (75 MHz, CDCl3): δ 22.55, 22.78, 26.64, 36.58, 56.41, 57.12, 66.70, 168.39; FT–IR (KBr, cm-1): 1065, 1070, 1621, 3278.

Refinement top

Hydrogen atoms bonded to C were positioned geometrically and refined using a riding model with fixed individual displacement parameters [U(H) = 1.2Ueq(C) or U(H) = 1.5 Ueq(Cmethyl)] using a riding model with Csp2—H = 0.95 Å, tertiary C—H = 0.98 Å, or methyl C—H = 0.96 Å, respectively. The methyl groups were allowed to rotate but not to tip. The H atoms bonded to N were refined isotropically with a distance restraint of 0.84 (1) Å.

Computing details top

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS (Siemens, 1994; data reduction: SHELXTL (Sheldrick, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of title compound in the solid state with 50% probability ellipsoids showing the labelling scheme. H atoms omitted for clarity.
[Figure 2] Fig. 2. Synthesis of the title compound.
(R)-N-{2-tert-Butyl-2-[(R)-tert- butylsulfonamido]ethylidene}-tert-butanesulfonamide top
Crystal data top
C14H30N2O2S2F(000) = 704
Mr = 322.52Dx = 1.131 Mg m−3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 9.714 (2) ÅCell parameters from 33 reflections
b = 18.489 (3) Åθ = 4.4–14.3°
c = 11.169 (2) ŵ = 0.29 mm−1
β = 109.23 (1)°T = 291 K
V = 1894.0 (7) Å3Block, colourless
Z = 40.52 × 0.42 × 0.38 mm
Data collection top
Siemens P4
diffractometer		5010 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tubeRint = 0.020
graphiteθmax = 25.5°, θmin = 1.9°
ω scansh = −11→11
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		k = −21→22
Tmin = 0.936, Tmax = 0.975l = −13→12
7793 measured reflections3 standard reflections every 97 reflections
6860 independent reflections intensity decay: 3.1%
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.039 w = 1/[σ2(Fo2) + (0.0406P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.084(Δ/σ)max = 0.001
S = 0.93Δρmax = 0.18 e Å−3
6860 reflectionsΔρmin = −0.14 e Å−3
388 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
3 restraintsExtinction coefficient: 0.0019 (5)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 3214 Friedel pairs
Secondary atom site location: difference Fourier mapFlack parameter: −0.04 (5)
Crystal data top
C14H30N2O2S2V = 1894.0 (7) Å3
Mr = 322.52Z = 4
Monoclinic, P21Mo Kα radiation
a = 9.714 (2) ŵ = 0.29 mm−1
b = 18.489 (3) ÅT = 291 K
c = 11.169 (2) Å0.52 × 0.42 × 0.38 mm
β = 109.23 (1)°
Data collection top
Siemens P4
diffractometer		5010 reflections with I > 2σ(I)
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		Rint = 0.020
Tmin = 0.936, Tmax = 0.975θmax = 25.5°
7793 measured reflections3 standard reflections every 97 reflections
6860 independent reflections intensity decay: 3.1%
Refinement top
R[F2 > 2σ(F2)] = 0.039H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.084Δρmax = 0.18 e Å−3
S = 0.93Δρmin = −0.14 e Å−3
6860 reflectionsAbsolute structure: Flack (1983), 3214 Friedel pairs
388 parametersFlack parameter: −0.04 (5)
3 restraints
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
S10.62185 (9)0.13531 (4)0.09753 (7)0.0524 (2)
S30.76902 (9)0.41227 (5)0.24900 (7)0.0597 (2)
O10.7320 (3)0.13867 (14)0.22466 (19)0.0841 (7)
O20.6577 (3)0.45966 (12)0.2718 (2)0.0877 (8)
N10.5765 (3)0.21702 (12)0.0354 (2)0.0438 (6)
N20.6898 (3)0.33949 (12)0.1602 (2)0.0483 (6)
C10.7187 (4)0.10552 (16)−0.0102 (3)0.0573 (8)
C20.6127 (4)0.1053 (2)−0.1445 (3)0.0836 (11)
H2A0.65940.0853−0.20050.100*
H2B0.58240.1540−0.16990.100*
H2C0.52910.0766−0.14820.100*
C30.8487 (3)0.15443 (18)0.0034 (3)0.0688 (9)
H3A0.91140.1322−0.03680.083*
H3B0.90170.16180.09170.083*
H3C0.81520.2002−0.03620.083*
C40.7696 (5)0.02897 (19)0.0361 (5)0.1111 (17)
H4A0.83320.03100.12250.133*
H4B0.82100.0085−0.01590.133*
H4C0.6865−0.00050.03090.133*
C50.4821 (3)0.25941 (14)0.0876 (3)0.0442 (7)
H50.46200.22940.15220.053*
C60.5596 (3)0.32531 (15)0.1532 (2)0.0490 (7)
H60.51100.35700.19010.059*
C70.8329 (3)0.45638 (15)0.1300 (3)0.0511 (7)
C80.9063 (4)0.52479 (18)0.1961 (3)0.0762 (10)
H8A0.94120.55240.13920.091*
H8B0.98680.51210.26990.091*
H8C0.83740.55310.22090.091*
C90.7062 (4)0.47343 (19)0.0140 (3)0.0759 (10)
H9A0.66430.4292−0.02720.091*
H9B0.73900.5021−0.04310.091*
H9C0.63420.49990.03780.091*
C100.9417 (4)0.4065 (2)0.1017 (4)0.0860 (11)
H10A0.99100.43210.05280.103*
H10B0.89160.36550.05440.103*
H10C1.01160.39040.17980.103*
C110.3333 (3)0.27616 (16)−0.0148 (3)0.0535 (8)
C120.3570 (3)0.3235 (2)−0.1180 (3)0.0729 (10)
H12A0.40120.3684−0.08150.087*
H12B0.26500.3331−0.18200.087*
H12C0.41990.2990−0.15530.087*
C130.2335 (4)0.3140 (2)0.0462 (3)0.0789 (10)
H13A0.23510.28820.12130.095*
H13B0.13580.3148−0.01260.095*
H13C0.26690.36260.06820.095*
C140.2615 (3)0.20401 (18)−0.0705 (4)0.0776 (10)
H14A0.16500.2130−0.12800.093*
H14B0.25610.1731−0.00310.093*
H14C0.31860.1809−0.11520.093*
S1'0.65069 (9)0.31033 (4)0.68082 (7)0.0563 (2)
S2'0.77418 (9)0.60677 (4)0.72095 (7)0.0623 (2)
O1'0.7423 (3)0.31879 (14)0.81314 (18)0.0963 (9)
O2'0.6581 (3)0.65720 (13)0.7277 (3)0.0954 (9)
N1'0.6110 (3)0.38924 (13)0.6060 (2)0.0512 (6)
N2'0.7029 (3)0.52435 (12)0.6713 (2)0.0524 (6)
C1'0.7708 (3)0.27604 (16)0.5946 (3)0.0561 (8)
C2'0.6810 (4)0.2677 (2)0.4578 (3)0.0813 (11)
H2'10.74160.25080.41100.098*
H2'20.63930.31350.42460.098*
H2'30.60440.23340.45020.098*
C3'0.8974 (4)0.3270 (2)0.6125 (4)0.0946 (12)
H3'10.97400.30230.59240.113*
H3'20.93290.34300.69910.113*
H3'30.86590.36800.55760.113*
C4'0.8225 (5)0.20221 (19)0.6538 (4)0.0909 (13)
H4'10.88280.20850.74060.109*
H4'20.87770.17880.60780.109*
H4'30.73960.17300.65030.109*
C5'0.5098 (3)0.43696 (14)0.6406 (3)0.0470 (7)
H5'0.49250.41640.71530.056*
C6'0.5765 (3)0.51004 (15)0.6755 (2)0.0501 (7)
H6'0.52460.54580.70080.060*
C7'0.8184 (3)0.63050 (17)0.5785 (3)0.0563 (8)
C8'0.8951 (4)0.70297 (18)0.6136 (4)0.0860 (11)
H8'10.91510.72250.54140.103*
H8'20.98500.69640.68200.103*
H8'30.83360.73570.63950.103*
C9'0.6820 (4)0.6364 (2)0.4637 (3)0.0875 (11)
H9'10.64330.58890.43830.105*
H9'20.70540.65890.39540.105*
H9'30.61070.66500.48470.105*
C10'0.9242 (4)0.57470 (19)0.5606 (4)0.0842 (11)
H10D1.00490.57000.63780.101*
H10E0.95910.58980.49360.101*
H10F0.87550.52900.53920.101*
C11'0.3593 (3)0.44309 (16)0.5317 (3)0.0534 (8)
C12'0.3752 (4)0.4788 (2)0.4167 (3)0.0739 (10)
H12D0.39470.52940.43330.089*
H12E0.28660.47300.34660.089*
H12F0.45440.45700.39650.089*
C13'0.2532 (4)0.4833 (2)0.5827 (4)0.0854 (11)
H13D0.15720.48160.52110.102*
H13E0.28350.53280.59900.102*
H13F0.25220.46090.65990.102*
C14'0.3006 (4)0.36648 (17)0.4980 (3)0.0754 (10)
H14D0.20410.36870.43730.090*
H14E0.29760.34230.57320.090*
H14F0.36330.34030.46250.090*
H1N0.6536 (17)0.2404 (12)0.046 (2)0.043 (8)*
H1'N0.686 (2)0.4126 (14)0.607 (3)0.059 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0687 (5)0.0399 (4)0.0566 (5)0.0111 (4)0.0316 (4)0.0094 (3)
S30.0751 (6)0.0619 (5)0.0430 (4)−0.0116 (5)0.0207 (4)−0.0050 (4)
O10.1006 (17)0.0986 (17)0.0521 (12)0.0434 (15)0.0237 (13)0.0181 (13)
O20.1073 (19)0.0810 (17)0.1057 (19)−0.0254 (14)0.0769 (17)−0.0468 (14)
N10.0430 (15)0.0394 (13)0.0545 (15)−0.0005 (12)0.0234 (12)0.0015 (11)
N20.0558 (16)0.0456 (14)0.0470 (14)0.0005 (12)0.0218 (12)0.0029 (10)
C10.074 (2)0.0438 (16)0.0651 (19)0.0105 (17)0.0382 (17)−0.0022 (16)
C20.097 (3)0.088 (3)0.076 (2)−0.018 (2)0.043 (2)−0.035 (2)
C30.060 (2)0.081 (3)0.071 (2)0.0117 (18)0.0299 (18)0.0029 (18)
C40.161 (4)0.051 (2)0.157 (4)0.037 (3)0.101 (4)0.014 (2)
C50.0469 (17)0.0418 (16)0.0514 (17)0.0042 (13)0.0263 (14)0.0074 (13)
C60.062 (2)0.0476 (18)0.0451 (16)0.0084 (15)0.0278 (15)0.0036 (13)
C70.0535 (18)0.0515 (17)0.0517 (17)−0.0040 (15)0.0220 (15)−0.0024 (14)
C80.080 (2)0.068 (2)0.083 (2)−0.015 (2)0.031 (2)−0.0081 (19)
C90.095 (3)0.074 (2)0.053 (2)−0.004 (2)0.016 (2)0.0147 (17)
C100.071 (2)0.087 (3)0.119 (3)−0.005 (2)0.058 (2)−0.024 (3)
C110.0447 (18)0.0539 (18)0.0653 (19)0.0076 (15)0.0225 (16)0.0109 (15)
C120.061 (2)0.088 (3)0.064 (2)0.0156 (19)0.0134 (17)0.0272 (19)
C130.063 (2)0.077 (2)0.106 (3)0.019 (2)0.041 (2)0.014 (2)
C140.052 (2)0.075 (2)0.097 (3)−0.0094 (18)0.013 (2)−0.005 (2)
S1'0.0768 (6)0.0515 (5)0.0470 (4)0.0158 (4)0.0288 (4)0.0094 (4)
S2'0.0675 (6)0.0626 (5)0.0584 (5)−0.0102 (5)0.0230 (4)−0.0121 (4)
O1'0.139 (2)0.0970 (18)0.0443 (12)0.0514 (18)0.0189 (13)0.0050 (13)
O2'0.1054 (19)0.0705 (17)0.141 (2)−0.0142 (15)0.0817 (18)−0.0438 (15)
N1'0.0530 (17)0.0495 (15)0.0553 (15)0.0082 (14)0.0238 (13)0.0069 (11)
N2'0.0523 (16)0.0532 (15)0.0516 (15)0.0041 (13)0.0168 (13)0.0018 (12)
C1'0.068 (2)0.0542 (19)0.0505 (18)0.0160 (17)0.0261 (16)0.0047 (15)
C2'0.108 (3)0.087 (3)0.055 (2)0.007 (2)0.034 (2)−0.0077 (19)
C3'0.068 (2)0.095 (3)0.125 (3)0.007 (2)0.038 (2)−0.004 (3)
C4'0.123 (3)0.074 (2)0.091 (3)0.046 (2)0.056 (3)0.021 (2)
C5'0.0494 (17)0.0515 (18)0.0452 (16)0.0010 (14)0.0223 (14)0.0036 (13)
C6'0.060 (2)0.0524 (18)0.0418 (16)0.0087 (15)0.0217 (15)0.0009 (14)
C7'0.0511 (17)0.0549 (19)0.0652 (19)0.0032 (16)0.0223 (16)−0.0015 (16)
C8'0.081 (3)0.072 (3)0.107 (3)−0.005 (2)0.033 (2)0.008 (2)
C9'0.076 (2)0.107 (3)0.076 (2)0.006 (2)0.019 (2)0.021 (2)
C10'0.083 (3)0.082 (3)0.108 (3)0.007 (2)0.059 (2)−0.006 (2)
C11'0.0448 (18)0.063 (2)0.0516 (18)0.0070 (16)0.0143 (15)0.0002 (15)
C12'0.066 (2)0.088 (3)0.058 (2)0.007 (2)0.0077 (18)0.0159 (19)
C13'0.062 (2)0.095 (3)0.099 (3)0.021 (2)0.025 (2)−0.013 (2)
C14'0.066 (2)0.065 (2)0.082 (2)−0.0054 (18)0.0073 (19)−0.0018 (19)
Geometric parameters (Å, °) top
S1—O11.471 (2)S1'—O1'1.461 (2)
S1—N11.661 (2)S1'—N1'1.662 (2)
S1—C11.839 (3)S1'—C1'1.852 (3)
S3—O21.478 (2)S2'—O2'1.484 (2)
S3—N21.698 (2)S2'—N2'1.690 (3)
S3—C71.833 (3)S2'—C7'1.833 (3)
N1—C51.465 (3)N1'—C5'1.464 (3)
N1—H1N0.838 (10)N1'—H1'N0.845 (10)
N2—C61.268 (3)N2'—C6'1.272 (3)
C1—C21.514 (4)C1'—C2'1.497 (4)
C1—C31.520 (4)C1'—C3'1.509 (5)
C1—C41.532 (4)C1'—C4'1.528 (4)
C2—H2A0.9600C2'—H2'10.9600
C2—H2B0.9600C2'—H2'20.9600
C2—H2C0.9600C2'—H2'30.9600
C3—H3A0.9600C3'—H3'10.9600
C3—H3B0.9600C3'—H3'20.9600
C3—H3C0.9600C3'—H3'30.9600
C4—H4A0.9600C4'—H4'10.9600
C4—H4B0.9600C4'—H4'20.9600
C4—H4C0.9600C4'—H4'30.9600
C5—C61.492 (4)C5'—C6'1.493 (4)
C5—C111.551 (4)C5'—C11'1.568 (4)
C5—H50.9800C5'—H5'0.9800
C6—H60.9300C6'—H6'0.9300
C7—C91.497 (4)C7'—C9'1.514 (4)
C7—C101.513 (4)C7'—C10'1.515 (4)
C7—C81.519 (4)C7'—C8'1.520 (4)
C8—H8A0.9600C8'—H8'10.9600
C8—H8B0.9600C8'—H8'20.9600
C8—H8C0.9600C8'—H8'30.9600
C9—H9A0.9600C9'—H9'10.9600
C9—H9B0.9600C9'—H9'20.9600
C9—H9C0.9600C9'—H9'30.9600
C10—H10A0.9600C10'—H10D0.9600
C10—H10B0.9600C10'—H10E0.9600
C10—H10C0.9600C10'—H10F0.9600
C11—C121.524 (4)C11'—C12'1.497 (4)
C11—C131.525 (4)C11'—C13'1.525 (4)
C11—C141.539 (4)C11'—C14'1.527 (4)
C12—H12A0.9600C12'—H12D0.9600
C12—H12B0.9600C12'—H12E0.9600
C12—H12C0.9600C12'—H12F0.9600
C13—H13A0.9600C13'—H13D0.9600
C13—H13B0.9600C13'—H13E0.9600
C13—H13C0.9600C13'—H13F0.9600
C14—H14A0.9600C14'—H14D0.9600
C14—H14B0.9600C14'—H14E0.9600
C14—H14C0.9600C14'—H14F0.9600
O1—S1—N1111.94 (14)O1'—S1'—N1'112.20 (14)
O1—S1—C1106.14 (14)O1'—S1'—C1'106.52 (15)
N1—S1—C196.97 (13)N1'—S1'—C1'96.92 (13)
O2—S3—N2110.71 (13)O2'—S2'—N2'110.32 (13)
O2—S3—C7107.61 (15)O2'—S2'—C7'107.03 (15)
N2—S3—C797.23 (12)N2'—S2'—C7'96.83 (13)
C5—N1—S1115.78 (18)C5'—N1'—S1'117.44 (19)
C5—N1—H1N108.2 (18)C5'—N1'—H1'N110 (2)
S1—N1—H1N107.9 (18)S1'—N1'—H1'N113 (2)
C6—N2—S3116.8 (2)C6'—N2'—S2'118.1 (2)
C2—C1—C3111.8 (3)C2'—C1'—C3'112.1 (3)
C2—C1—C4111.8 (3)C2'—C1'—C4'110.3 (3)
C3—C1—C4110.6 (3)C3'—C1'—C4'111.3 (3)
C2—C1—S1108.7 (2)C2'—C1'—S1'108.1 (2)
C3—C1—S1110.1 (2)C3'—C1'—S1'110.1 (2)
C4—C1—S1103.5 (2)C4'—C1'—S1'104.7 (2)
C1—C2—H2A109.5C1'—C2'—H2'1109.5
C1—C2—H2B109.5C1'—C2'—H2'2109.5
H2A—C2—H2B109.5H2'1—C2'—H2'2109.5
C1—C2—H2C109.5C1'—C2'—H2'3109.5
H2A—C2—H2C109.5H2'1—C2'—H2'3109.5
H2B—C2—H2C109.5H2'2—C2'—H2'3109.5
C1—C3—H3A109.5C1'—C3'—H3'1109.5
C1—C3—H3B109.5C1'—C3'—H3'2109.5
H3A—C3—H3B109.5H3'1—C3'—H3'2109.5
C1—C3—H3C109.5C1'—C3'—H3'3109.5
H3A—C3—H3C109.5H3'1—C3'—H3'3109.5
H3B—C3—H3C109.5H3'2—C3'—H3'3109.5
C1—C4—H4A109.5C1'—C4'—H4'1109.5
C1—C4—H4B109.5C1'—C4'—H4'2109.5
H4A—C4—H4B109.5H4'1—C4'—H4'2109.5
C1—C4—H4C109.5C1'—C4'—H4'3109.5
H4A—C4—H4C109.5H4'1—C4'—H4'3109.5
H4B—C4—H4C109.5H4'2—C4'—H4'3109.5
N1—C5—C6110.6 (2)N1'—C5'—C6'110.1 (2)
N1—C5—C11111.5 (2)N1'—C5'—C11'112.0 (2)
C6—C5—C11113.3 (2)C6'—C5'—C11'110.5 (2)
N1—C5—H5107.0N1'—C5'—H5'108.1
C6—C5—H5107.0C6'—C5'—H5'108.1
C11—C5—H5107.0C11'—C5'—H5'108.1
N2—C6—C5122.1 (2)N2'—C6'—C5'121.3 (2)
N2—C6—H6119.0N2'—C6'—H6'119.4
C5—C6—H6119.0C5'—C6'—H6'119.4
C9—C7—C10112.3 (3)C9'—C7'—C10'112.3 (3)
C9—C7—C8111.5 (3)C9'—C7'—C8'111.9 (3)
C10—C7—C8111.1 (3)C10'—C7'—C8'109.8 (3)
C9—C7—S3110.1 (2)C9'—C7'—S2'111.2 (2)
C10—C7—S3107.9 (2)C10'—C7'—S2'108.3 (2)
C8—C7—S3103.6 (2)C8'—C7'—S2'102.8 (2)
C7—C8—H8A109.5C7'—C8'—H8'1109.5
C7—C8—H8B109.5C7'—C8'—H8'2109.5
H8A—C8—H8B109.5H8'1—C8'—H8'2109.5
C7—C8—H8C109.5C7'—C8'—H8'3109.5
H8A—C8—H8C109.5H8'1—C8'—H8'3109.5
H8B—C8—H8C109.5H8'2—C8'—H8'3109.5
C7—C9—H9A109.5C7'—C9'—H9'1109.5
C7—C9—H9B109.5C7'—C9'—H9'2109.5
H9A—C9—H9B109.5H9'1—C9'—H9'2109.5
C7—C9—H9C109.5C7'—C9'—H9'3109.5
H9A—C9—H9C109.5H9'1—C9'—H9'3109.5
H9B—C9—H9C109.5H9'2—C9'—H9'3109.5
C7—C10—H10A109.5C7'—C10'—H10D109.5
C7—C10—H10B109.5C7'—C10'—H10E109.5
H10A—C10—H10B109.5H10D—C10'—H10E109.5
C7—C10—H10C109.5C7'—C10'—H10F109.5
H10A—C10—H10C109.5H10D—C10'—H10F109.5
H10B—C10—H10C109.5H10E—C10'—H10F109.5
C12—C11—C13110.6 (3)C12'—C11'—C13'112.2 (3)
C12—C11—C14110.7 (3)C12'—C11'—C14'109.5 (3)
C13—C11—C14107.9 (3)C13'—C11'—C14'107.5 (3)
C12—C11—C5109.6 (2)C12'—C11'—C5'111.4 (3)
C13—C11—C5109.7 (2)C13'—C11'—C5'108.5 (2)
C14—C11—C5108.3 (2)C14'—C11'—C5'107.5 (2)
C11—C12—H12A109.5C11'—C12'—H12D109.5
C11—C12—H12B109.5C11'—C12'—H12E109.5
H12A—C12—H12B109.5H12D—C12'—H12E109.5
C11—C12—H12C109.5C11'—C12'—H12F109.5
H12A—C12—H12C109.5H12D—C12'—H12F109.5
H12B—C12—H12C109.5H12E—C12'—H12F109.5
C11—C13—H13A109.5C11'—C13'—H13D109.5
C11—C13—H13B109.5C11'—C13'—H13E109.5
H13A—C13—H13B109.5H13D—C13'—H13E109.5
C11—C13—H13C109.5C11'—C13'—H13F109.5
H13A—C13—H13C109.5H13D—C13'—H13F109.5
H13B—C13—H13C109.5H13E—C13'—H13F109.5
C11—C14—H14A109.5C11'—C14'—H14D109.5
C11—C14—H14B109.5C11'—C14'—H14E109.5
H14A—C14—H14B109.5H14D—C14'—H14E109.5
C11—C14—H14C109.5C11'—C14'—H14F109.5
H14A—C14—H14C109.5H14D—C14'—H14F109.5
H14B—C14—H14C109.5H14E—C14'—H14F109.5
O1—S1—N1—C5−74.9 (2)O1'—S1'—N1'—C5'−71.0 (3)
C1—S1—N1—C5174.6 (2)C1'—S1'—N1'—C5'178.0 (2)
O2—S3—N2—C6−17.2 (2)O2'—S2'—N2'—C6'−16.3 (3)
C7—S3—N2—C6−129.1 (2)C7'—S2'—N2'—C6'−127.3 (2)
O1—S1—C1—C2−176.6 (2)O1'—S1'—C1'—C2'−179.2 (2)
N1—S1—C1—C2−61.3 (2)N1'—S1'—C1'—C2'−63.5 (2)
O1—S1—C1—C3−53.7 (2)O1'—S1'—C1'—C3'−56.5 (3)
N1—S1—C1—C361.5 (2)N1'—S1'—C1'—C3'59.1 (3)
O1—S1—C1—C464.4 (3)O1'—S1'—C1'—C4'63.2 (3)
N1—S1—C1—C4179.7 (3)N1'—S1'—C1'—C4'178.8 (2)
S1—N1—C5—C6115.5 (2)S1'—N1'—C5'—C6'126.5 (2)
S1—N1—C5—C11−117.4 (2)S1'—N1'—C5'—C11'−110.2 (2)
S3—N2—C6—C5−174.66 (18)S2'—N2'—C6'—C5'−176.3 (2)
N1—C5—C6—N2−0.4 (3)N1'—C5'—C6'—N2'0.9 (4)
C11—C5—C6—N2−126.5 (3)C11'—C5'—C6'—N2'−123.3 (3)
O2—S3—C7—C9−54.5 (3)O2'—S2'—C7'—C9'−49.8 (3)
N2—S3—C7—C959.9 (2)N2'—S2'—C7'—C9'64.0 (3)
O2—S3—C7—C10−177.4 (2)O2'—S2'—C7'—C10'−173.7 (2)
N2—S3—C7—C10−62.9 (2)N2'—S2'—C7'—C10'−59.9 (2)
O2—S3—C7—C864.7 (2)O2'—S2'—C7'—C8'70.2 (2)
N2—S3—C7—C8179.2 (2)N2'—S2'—C7'—C8'−176.1 (2)
N1—C5—C11—C12−63.8 (3)N1'—C5'—C11'—C12'−65.0 (3)
C6—C5—C11—C1261.8 (3)C6'—C5'—C11'—C12'58.1 (3)
N1—C5—C11—C13174.6 (2)N1'—C5'—C11'—C13'171.0 (3)
C6—C5—C11—C13−59.8 (3)C6'—C5'—C11'—C13'−65.9 (3)
N1—C5—C11—C1457.1 (3)N1'—C5'—C11'—C14'54.9 (3)
C6—C5—C11—C14−177.3 (2)C6'—C5'—C11'—C14'178.0 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···N20.84 (2)2.19 (2)2.697 (3)119.(2)
N1'—H1'N···N2'0.84 (2)2.18 (3)2.672 (3)118 (2)
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···N20.84 (2)2.19 (2)2.697 (3)119.(2)
N1'—H1'N···N2'0.84 (2)2.18 (3)2.672 (3)118 (2)
Acknowledgements top

This work was supported by the Science Fund of the Education Office of Jiangxi, China ([2007]279).

references
References top

Alexakis, A., Tomassini, A., Chouillet, C., Roland, S., Mangeney, P. & Bernardinelli, G. (2000). Angew. Chem. Int. Ed. 39, 4093–4095.

Alvaro, J., Grepioni, F. & Savoia, D. (1997). J. Org. Chem. 62, 4180–4182.

Bambridge, K., Begley, M. J. & Simpkins, N. S. (1994). Tetrahedron Lett. 35, 3391–3394.

Flack, H. D. (1983). Acta Cryst. A39, 876–881.

Lucet, D., Le Gall, T. & Mioskowski, C. (1998). Angew. Chem. Int. Ed. 37, 2580–2627.

Roland, S. & Mangeney, P. (2000). Eur. J. Org. Chem. pp. 611–616.

Roland, S., Mangeney, P. & Alexakis, A. (1999). Synthesis, 2, 228–230.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Siemens (1994). XSCANS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin USA.

Sun, X.-X., Wang, S.-J., Zhu, J. & Deng, J.-G. (2005). Synlett, 18, 2776–2781.