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

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

doi:10.1107/S1600536808028225

organic compounds

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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page o1913

doi:10.1107/S1600536808028225

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

Yu Hu,^a Xiao-Xia Sun ^b ^* and Cong-Bin Fan ^b

^aExperimental Chemistry Center, Nanchang University, Nanchang 330031, People's Republic of China, and ^bJiangxi Key Laboratory of Organic Chemistry, Jiangxi Science and Technology Normal University, Nanchang 330013, People's Republic of China
^*Correspondence e-mail: sunxiaoxia77@yahoo.cn.

(Received 27 August 2008; accepted 3 September 2008; online 13 September 2008)

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.

Related literature

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

Experimental

Crystal data

C₁₄H₃₀N₂O₂S₂
M_r = 322.52
Monoclinic, P 2₁
a = 9.714 (2) Å
b = 18.489 (3) Å
c = 11.169 (2) Å
β = 109.23 (1)°
V = 1894.0 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 291 (2) K
0.52 × 0.42 × 0.38 mm

Data collection

Siemens P4 diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.936, T_max = 0.975 (expected range = 0.862–0.897)
7793 measured reflections
6860 independent reflections
5010 reflections with I > 2σ(I)
R_int = 0.020
3 standard reflections every 97 reflections intensity decay: 3.1%

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.084
S = 0.93
6860 reflections
388 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.14 e Å⁻³
Absolute structure: Flack (1983 ), 3214 Friedel pairs
Flack parameter: −0.04 (5)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯N2	0.84 (2)	2.19 (2)	2.697 (3)	118.5 (17)
N1′—H1′N⋯N2′	0.84 (2)	2.18 (3)	2.672 (3)	118 (2)

Data collection: XSCANS (Siemens, 1994 ); cell refinement: XSCANS; 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; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808028225/bt2777sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808028225/bt2777Isup2.hkl

checkCIF report

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.

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

	Fig. 1. Molecular structure of title compound in the solid state with 50% probability ellipsoids showing the labelling scheme. H atoms omitted for clarity.
	Fig. 2. Synthesis of the title compound.

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

Crystal data top

C₁₄H₃₀N₂O₂S₂	F(000) = 704
M_r = 322.52	D_x = 1.131 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 9.714 (2) Å	Cell parameters from 33 reflections
b = 18.489 (3) Å	θ = 4.4–14.3°
c = 11.169 (2) Å	µ = 0.29 mm⁻¹
β = 109.23 (1)°	T = 291 K
V = 1894.0 (7) Å³	Block, colourless
Z = 4	0.52 × 0.42 × 0.38 mm

Data collection top

Siemens P4 diffractometer	5010 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tube	R_int = 0.020
Graphite monochromator	θ_max = 25.5°, θ_min = 1.9°
ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −21→22
T_min = 0.936, T_max = 0.975	l = −13→12
7793 measured reflections	3 standard reflections every 97 reflections
6860 independent reflections	intensity decay: 3.1%

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.039	w = 1/[σ²(F_o²) + (0.0406P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.084	(Δ/σ)_max = 0.001
S = 0.93	Δρ_max = 0.18 e Å⁻³
6860 reflections	Δρ_min = −0.14 e Å⁻³
388 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
3 restraints	Extinction coefficient: 0.0019 (5)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 3214 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.04 (5)

Crystal data top

C₁₄H₃₀N₂O₂S₂	V = 1894.0 (7) Å³
M_r = 322.52	Z = 4
Monoclinic, P2₁	Mo Kα radiation
a = 9.714 (2) Å	µ = 0.29 mm⁻¹
b = 18.489 (3) Å	T = 291 K
c = 11.169 (2) Å	0.52 × 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)	R_int = 0.020
T_min = 0.936, T_max = 0.975	3 standard reflections every 97 reflections
7793 measured reflections	intensity decay: 3.1%
6860 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.084	Δρ_max = 0.18 e Å⁻³
S = 0.93	Δρ_min = −0.14 e Å⁻³
6860 reflections	Absolute structure: Flack (1983), 3214 Friedel pairs
388 parameters	Absolute structure 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

	x	y	z	U_iso*/U_eq
S1	0.62185 (9)	0.13531 (4)	0.09753 (7)	0.0524 (2)
S3	0.76902 (9)	0.41227 (5)	0.24900 (7)	0.0597 (2)
O1	0.7320 (3)	0.13867 (14)	0.22466 (19)	0.0841 (7)
O2	0.6577 (3)	0.45966 (12)	0.2718 (2)	0.0877 (8)
N1	0.5765 (3)	0.21702 (12)	0.0354 (2)	0.0438 (6)
N2	0.6898 (3)	0.33949 (12)	0.1602 (2)	0.0483 (6)
C1	0.7187 (4)	0.10552 (16)	−0.0102 (3)	0.0573 (8)
C2	0.6127 (4)	0.1053 (2)	−0.1445 (3)	0.0836 (11)
H2A	0.6594	0.0853	−0.2005	0.100*
H2B	0.5824	0.1540	−0.1699	0.100*
H2C	0.5291	0.0766	−0.1482	0.100*
C3	0.8487 (3)	0.15443 (18)	0.0034 (3)	0.0688 (9)
H3A	0.9114	0.1322	−0.0368	0.083*
H3B	0.9017	0.1618	0.0917	0.083*
H3C	0.8152	0.2002	−0.0362	0.083*
C4	0.7696 (5)	0.02897 (19)	0.0361 (5)	0.1111 (17)
H4A	0.8332	0.0310	0.1225	0.133*
H4B	0.8210	0.0085	−0.0159	0.133*
H4C	0.6865	−0.0005	0.0309	0.133*
C5	0.4821 (3)	0.25941 (14)	0.0876 (3)	0.0442 (7)
H5	0.4620	0.2294	0.1522	0.053*
C6	0.5596 (3)	0.32531 (15)	0.1532 (2)	0.0490 (7)
H6	0.5110	0.3570	0.1901	0.059*
C7	0.8329 (3)	0.45638 (15)	0.1300 (3)	0.0511 (7)
C8	0.9063 (4)	0.52479 (18)	0.1961 (3)	0.0762 (10)
H8A	0.9412	0.5524	0.1392	0.091*
H8B	0.9868	0.5121	0.2699	0.091*
H8C	0.8374	0.5531	0.2209	0.091*
C9	0.7062 (4)	0.47343 (19)	0.0140 (3)	0.0759 (10)
H9A	0.6643	0.4292	−0.0272	0.091*
H9B	0.7390	0.5021	−0.0431	0.091*
H9C	0.6342	0.4999	0.0378	0.091*
C10	0.9417 (4)	0.4065 (2)	0.1017 (4)	0.0860 (11)
H10A	0.9910	0.4321	0.0528	0.103*
H10B	0.8916	0.3655	0.0544	0.103*
H10C	1.0116	0.3904	0.1798	0.103*
C11	0.3333 (3)	0.27616 (16)	−0.0148 (3)	0.0535 (8)
C12	0.3570 (3)	0.3235 (2)	−0.1180 (3)	0.0729 (10)
H12A	0.4012	0.3684	−0.0815	0.087*
H12B	0.2650	0.3331	−0.1820	0.087*
H12C	0.4199	0.2990	−0.1553	0.087*
C13	0.2335 (4)	0.3140 (2)	0.0462 (3)	0.0789 (10)
H13A	0.2351	0.2882	0.1213	0.095*
H13B	0.1358	0.3148	−0.0126	0.095*
H13C	0.2669	0.3626	0.0682	0.095*
C14	0.2615 (3)	0.20401 (18)	−0.0705 (4)	0.0776 (10)
H14A	0.1650	0.2130	−0.1280	0.093*
H14B	0.2561	0.1731	−0.0031	0.093*
H14C	0.3186	0.1809	−0.1152	0.093*
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)
H2'1	0.7416	0.2508	0.4110	0.098*
H2'2	0.6393	0.3135	0.4246	0.098*
H2'3	0.6044	0.2334	0.4502	0.098*
C3'	0.8974 (4)	0.3270 (2)	0.6125 (4)	0.0946 (12)
H3'1	0.9740	0.3023	0.5924	0.113*
H3'2	0.9329	0.3430	0.6991	0.113*
H3'3	0.8659	0.3680	0.5576	0.113*
C4'	0.8225 (5)	0.20221 (19)	0.6538 (4)	0.0909 (13)
H4'1	0.8828	0.2085	0.7406	0.109*
H4'2	0.8777	0.1788	0.6078	0.109*
H4'3	0.7396	0.1730	0.6503	0.109*
C5'	0.5098 (3)	0.43696 (14)	0.6406 (3)	0.0470 (7)
H5'	0.4925	0.4164	0.7153	0.056*
C6'	0.5765 (3)	0.51004 (15)	0.6755 (2)	0.0501 (7)
H6'	0.5246	0.5458	0.7008	0.060*
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)
H8'1	0.9151	0.7225	0.5414	0.103*
H8'2	0.9850	0.6964	0.6820	0.103*
H8'3	0.8336	0.7357	0.6395	0.103*
C9'	0.6820 (4)	0.6364 (2)	0.4637 (3)	0.0875 (11)
H9'1	0.6433	0.5889	0.4383	0.105*
H9'2	0.7054	0.6589	0.3954	0.105*
H9'3	0.6107	0.6650	0.4847	0.105*
C10'	0.9242 (4)	0.57470 (19)	0.5606 (4)	0.0842 (11)
H10D	1.0049	0.5700	0.6378	0.101*
H10E	0.9591	0.5898	0.4936	0.101*
H10F	0.8755	0.5290	0.5392	0.101*
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)
H12D	0.3947	0.5294	0.4333	0.089*
H12E	0.2866	0.4730	0.3466	0.089*
H12F	0.4544	0.4570	0.3965	0.089*
C13'	0.2532 (4)	0.4833 (2)	0.5827 (4)	0.0854 (11)
H13D	0.1572	0.4816	0.5211	0.102*
H13E	0.2835	0.5328	0.5990	0.102*
H13F	0.2522	0.4609	0.6599	0.102*
C14'	0.3006 (4)	0.36648 (17)	0.4980 (3)	0.0754 (10)
H14D	0.2041	0.3687	0.4373	0.090*
H14E	0.2976	0.3423	0.5732	0.090*
H14F	0.3633	0.3403	0.4625	0.090*
H1N	0.6536 (17)	0.2404 (12)	0.046 (2)	0.043 (8)*
H1'N	0.686 (2)	0.4126 (14)	0.607 (3)	0.059 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0687 (5)	0.0399 (4)	0.0566 (5)	0.0111 (4)	0.0316 (4)	0.0094 (3)
S3	0.0751 (6)	0.0619 (5)	0.0430 (4)	−0.0116 (5)	0.0207 (4)	−0.0050 (4)
O1	0.1006 (17)	0.0986 (17)	0.0521 (12)	0.0434 (15)	0.0237 (13)	0.0181 (13)
O2	0.1073 (19)	0.0810 (17)	0.1057 (19)	−0.0254 (14)	0.0769 (17)	−0.0468 (14)
N1	0.0430 (15)	0.0394 (13)	0.0545 (15)	−0.0005 (12)	0.0234 (12)	0.0015 (11)
N2	0.0558 (16)	0.0456 (14)	0.0470 (14)	0.0005 (12)	0.0218 (12)	0.0029 (10)
C1	0.074 (2)	0.0438 (16)	0.0651 (19)	0.0105 (17)	0.0382 (17)	−0.0022 (16)
C2	0.097 (3)	0.088 (3)	0.076 (2)	−0.018 (2)	0.043 (2)	−0.035 (2)
C3	0.060 (2)	0.081 (3)	0.071 (2)	0.0117 (18)	0.0299 (18)	0.0029 (18)
C4	0.161 (4)	0.051 (2)	0.157 (4)	0.037 (3)	0.101 (4)	0.014 (2)
C5	0.0469 (17)	0.0418 (16)	0.0514 (17)	0.0042 (13)	0.0263 (14)	0.0074 (13)
C6	0.062 (2)	0.0476 (18)	0.0451 (16)	0.0084 (15)	0.0278 (15)	0.0036 (13)
C7	0.0535 (18)	0.0515 (17)	0.0517 (17)	−0.0040 (15)	0.0220 (15)	−0.0024 (14)
C8	0.080 (2)	0.068 (2)	0.083 (2)	−0.015 (2)	0.031 (2)	−0.0081 (19)
C9	0.095 (3)	0.074 (2)	0.053 (2)	−0.004 (2)	0.016 (2)	0.0147 (17)
C10	0.071 (2)	0.087 (3)	0.119 (3)	−0.005 (2)	0.058 (2)	−0.024 (3)
C11	0.0447 (18)	0.0539 (18)	0.0653 (19)	0.0076 (15)	0.0225 (16)	0.0109 (15)
C12	0.061 (2)	0.088 (3)	0.064 (2)	0.0156 (19)	0.0134 (17)	0.0272 (19)
C13	0.063 (2)	0.077 (2)	0.106 (3)	0.019 (2)	0.041 (2)	0.014 (2)
C14	0.052 (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, º) top

S1—O1	1.471 (2)	S1'—O1'	1.461 (2)
S1—N1	1.661 (2)	S1'—N1'	1.662 (2)
S1—C1	1.839 (3)	S1'—C1'	1.852 (3)
S3—O2	1.478 (2)	S2'—O2'	1.484 (2)
S3—N2	1.698 (2)	S2'—N2'	1.690 (3)
S3—C7	1.833 (3)	S2'—C7'	1.833 (3)
N1—C5	1.465 (3)	N1'—C5'	1.464 (3)
N1—H1N	0.838 (10)	N1'—H1'N	0.845 (10)
N2—C6	1.268 (3)	N2'—C6'	1.272 (3)
C1—C2	1.514 (4)	C1'—C2'	1.497 (4)
C1—C3	1.520 (4)	C1'—C3'	1.509 (5)
C1—C4	1.532 (4)	C1'—C4'	1.528 (4)
C2—H2A	0.9600	C2'—H2'1	0.9600
C2—H2B	0.9600	C2'—H2'2	0.9600
C2—H2C	0.9600	C2'—H2'3	0.9600
C3—H3A	0.9600	C3'—H3'1	0.9600
C3—H3B	0.9600	C3'—H3'2	0.9600
C3—H3C	0.9600	C3'—H3'3	0.9600
C4—H4A	0.9600	C4'—H4'1	0.9600
C4—H4B	0.9600	C4'—H4'2	0.9600
C4—H4C	0.9600	C4'—H4'3	0.9600
C5—C6	1.492 (4)	C5'—C6'	1.493 (4)
C5—C11	1.551 (4)	C5'—C11'	1.568 (4)
C5—H5	0.9800	C5'—H5'	0.9800
C6—H6	0.9300	C6'—H6'	0.9300
C7—C9	1.497 (4)	C7'—C9'	1.514 (4)
C7—C10	1.513 (4)	C7'—C10'	1.515 (4)
C7—C8	1.519 (4)	C7'—C8'	1.520 (4)
C8—H8A	0.9600	C8'—H8'1	0.9600
C8—H8B	0.9600	C8'—H8'2	0.9600
C8—H8C	0.9600	C8'—H8'3	0.9600
C9—H9A	0.9600	C9'—H9'1	0.9600
C9—H9B	0.9600	C9'—H9'2	0.9600
C9—H9C	0.9600	C9'—H9'3	0.9600
C10—H10A	0.9600	C10'—H10D	0.9600
C10—H10B	0.9600	C10'—H10E	0.9600
C10—H10C	0.9600	C10'—H10F	0.9600
C11—C12	1.524 (4)	C11'—C12'	1.497 (4)
C11—C13	1.525 (4)	C11'—C13'	1.525 (4)
C11—C14	1.539 (4)	C11'—C14'	1.527 (4)
C12—H12A	0.9600	C12'—H12D	0.9600
C12—H12B	0.9600	C12'—H12E	0.9600
C12—H12C	0.9600	C12'—H12F	0.9600
C13—H13A	0.9600	C13'—H13D	0.9600
C13—H13B	0.9600	C13'—H13E	0.9600
C13—H13C	0.9600	C13'—H13F	0.9600
C14—H14A	0.9600	C14'—H14D	0.9600
C14—H14B	0.9600	C14'—H14E	0.9600
C14—H14C	0.9600	C14'—H14F	0.9600

O1—S1—N1	111.94 (14)	O1'—S1'—N1'	112.20 (14)
O1—S1—C1	106.14 (14)	O1'—S1'—C1'	106.52 (15)
N1—S1—C1	96.97 (13)	N1'—S1'—C1'	96.92 (13)
O2—S3—N2	110.71 (13)	O2'—S2'—N2'	110.32 (13)
O2—S3—C7	107.61 (15)	O2'—S2'—C7'	107.03 (15)
N2—S3—C7	97.23 (12)	N2'—S2'—C7'	96.83 (13)
C5—N1—S1	115.78 (18)	C5'—N1'—S1'	117.44 (19)
C5—N1—H1N	108.2 (18)	C5'—N1'—H1'N	110 (2)
S1—N1—H1N	107.9 (18)	S1'—N1'—H1'N	113 (2)
C6—N2—S3	116.8 (2)	C6'—N2'—S2'	118.1 (2)
C2—C1—C3	111.8 (3)	C2'—C1'—C3'	112.1 (3)
C2—C1—C4	111.8 (3)	C2'—C1'—C4'	110.3 (3)
C3—C1—C4	110.6 (3)	C3'—C1'—C4'	111.3 (3)
C2—C1—S1	108.7 (2)	C2'—C1'—S1'	108.1 (2)
C3—C1—S1	110.1 (2)	C3'—C1'—S1'	110.1 (2)
C4—C1—S1	103.5 (2)	C4'—C1'—S1'	104.7 (2)
C1—C2—H2A	109.5	C1'—C2'—H2'1	109.5
C1—C2—H2B	109.5	C1'—C2'—H2'2	109.5
H2A—C2—H2B	109.5	H2'1—C2'—H2'2	109.5
C1—C2—H2C	109.5	C1'—C2'—H2'3	109.5
H2A—C2—H2C	109.5	H2'1—C2'—H2'3	109.5
H2B—C2—H2C	109.5	H2'2—C2'—H2'3	109.5
C1—C3—H3A	109.5	C1'—C3'—H3'1	109.5
C1—C3—H3B	109.5	C1'—C3'—H3'2	109.5
H3A—C3—H3B	109.5	H3'1—C3'—H3'2	109.5
C1—C3—H3C	109.5	C1'—C3'—H3'3	109.5
H3A—C3—H3C	109.5	H3'1—C3'—H3'3	109.5
H3B—C3—H3C	109.5	H3'2—C3'—H3'3	109.5
C1—C4—H4A	109.5	C1'—C4'—H4'1	109.5
C1—C4—H4B	109.5	C1'—C4'—H4'2	109.5
H4A—C4—H4B	109.5	H4'1—C4'—H4'2	109.5
C1—C4—H4C	109.5	C1'—C4'—H4'3	109.5
H4A—C4—H4C	109.5	H4'1—C4'—H4'3	109.5
H4B—C4—H4C	109.5	H4'2—C4'—H4'3	109.5
N1—C5—C6	110.6 (2)	N1'—C5'—C6'	110.1 (2)
N1—C5—C11	111.5 (2)	N1'—C5'—C11'	112.0 (2)
C6—C5—C11	113.3 (2)	C6'—C5'—C11'	110.5 (2)
N1—C5—H5	107.0	N1'—C5'—H5'	108.1
C6—C5—H5	107.0	C6'—C5'—H5'	108.1
C11—C5—H5	107.0	C11'—C5'—H5'	108.1
N2—C6—C5	122.1 (2)	N2'—C6'—C5'	121.3 (2)
N2—C6—H6	119.0	N2'—C6'—H6'	119.4
C5—C6—H6	119.0	C5'—C6'—H6'	119.4
C9—C7—C10	112.3 (3)	C9'—C7'—C10'	112.3 (3)
C9—C7—C8	111.5 (3)	C9'—C7'—C8'	111.9 (3)
C10—C7—C8	111.1 (3)	C10'—C7'—C8'	109.8 (3)
C9—C7—S3	110.1 (2)	C9'—C7'—S2'	111.2 (2)
C10—C7—S3	107.9 (2)	C10'—C7'—S2'	108.3 (2)
C8—C7—S3	103.6 (2)	C8'—C7'—S2'	102.8 (2)
C7—C8—H8A	109.5	C7'—C8'—H8'1	109.5
C7—C8—H8B	109.5	C7'—C8'—H8'2	109.5
H8A—C8—H8B	109.5	H8'1—C8'—H8'2	109.5
C7—C8—H8C	109.5	C7'—C8'—H8'3	109.5
H8A—C8—H8C	109.5	H8'1—C8'—H8'3	109.5
H8B—C8—H8C	109.5	H8'2—C8'—H8'3	109.5
C7—C9—H9A	109.5	C7'—C9'—H9'1	109.5
C7—C9—H9B	109.5	C7'—C9'—H9'2	109.5
H9A—C9—H9B	109.5	H9'1—C9'—H9'2	109.5
C7—C9—H9C	109.5	C7'—C9'—H9'3	109.5
H9A—C9—H9C	109.5	H9'1—C9'—H9'3	109.5
H9B—C9—H9C	109.5	H9'2—C9'—H9'3	109.5
C7—C10—H10A	109.5	C7'—C10'—H10D	109.5
C7—C10—H10B	109.5	C7'—C10'—H10E	109.5
H10A—C10—H10B	109.5	H10D—C10'—H10E	109.5
C7—C10—H10C	109.5	C7'—C10'—H10F	109.5
H10A—C10—H10C	109.5	H10D—C10'—H10F	109.5
H10B—C10—H10C	109.5	H10E—C10'—H10F	109.5
C12—C11—C13	110.6 (3)	C12'—C11'—C13'	112.2 (3)
C12—C11—C14	110.7 (3)	C12'—C11'—C14'	109.5 (3)
C13—C11—C14	107.9 (3)	C13'—C11'—C14'	107.5 (3)
C12—C11—C5	109.6 (2)	C12'—C11'—C5'	111.4 (3)
C13—C11—C5	109.7 (2)	C13'—C11'—C5'	108.5 (2)
C14—C11—C5	108.3 (2)	C14'—C11'—C5'	107.5 (2)
C11—C12—H12A	109.5	C11'—C12'—H12D	109.5
C11—C12—H12B	109.5	C11'—C12'—H12E	109.5
H12A—C12—H12B	109.5	H12D—C12'—H12E	109.5
C11—C12—H12C	109.5	C11'—C12'—H12F	109.5
H12A—C12—H12C	109.5	H12D—C12'—H12F	109.5
H12B—C12—H12C	109.5	H12E—C12'—H12F	109.5
C11—C13—H13A	109.5	C11'—C13'—H13D	109.5
C11—C13—H13B	109.5	C11'—C13'—H13E	109.5
H13A—C13—H13B	109.5	H13D—C13'—H13E	109.5
C11—C13—H13C	109.5	C11'—C13'—H13F	109.5
H13A—C13—H13C	109.5	H13D—C13'—H13F	109.5
H13B—C13—H13C	109.5	H13E—C13'—H13F	109.5
C11—C14—H14A	109.5	C11'—C14'—H14D	109.5
C11—C14—H14B	109.5	C11'—C14'—H14E	109.5
H14A—C14—H14B	109.5	H14D—C14'—H14E	109.5
C11—C14—H14C	109.5	C11'—C14'—H14F	109.5
H14A—C14—H14C	109.5	H14D—C14'—H14F	109.5
H14B—C14—H14C	109.5	H14E—C14'—H14F	109.5

O1—S1—N1—C5	−74.9 (2)	O1'—S1'—N1'—C5'	−71.0 (3)
C1—S1—N1—C5	174.6 (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—C3	61.5 (2)	N1'—S1'—C1'—C3'	59.1 (3)
O1—S1—C1—C4	64.4 (3)	O1'—S1'—C1'—C4'	63.2 (3)
N1—S1—C1—C4	179.7 (3)	N1'—S1'—C1'—C4'	178.8 (2)
S1—N1—C5—C6	115.5 (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—C9	59.9 (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—C8	64.7 (2)	O2'—S2'—C7'—C8'	70.2 (2)
N2—S3—C7—C8	179.2 (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—C12	61.8 (3)	C6'—C5'—C11'—C12'	58.1 (3)
N1—C5—C11—C13	174.6 (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—C14	57.1 (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, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N2	0.84 (2)	2.19 (2)	2.697 (3)	119 (2)
N1′—H1′N···N2′	0.84 (2)	2.18 (3)	2.672 (3)	118 (2)

Experimental details

Crystal data
Chemical formula	C₁₄H₃₀N₂O₂S₂
M_r	322.52
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	291
a, b, c (Å)	9.714 (2), 18.489 (3), 11.169 (2)
β (°)	109.23 (1)
V (Å³)	1894.0 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.52 × 0.42 × 0.38

Data collection
Diffractometer	Siemens P4 diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.936, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	7793, 6860, 5010
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.084, 0.93
No. of reflections	6860
No. of parameters	388
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.14
Absolute structure	Flack (1983), 3214 Friedel pairs
Absolute structure parameter	−0.04 (5)

Computer programs: XSCANS (Siemens, 1994), XSCANS (Siemens, 1994, SHELXTL (Sheldrick, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N2	0.84 (2)	2.19 (2)	2.697 (3)	118.5 (17)
N1'—H1'N···N2'	0.84 (2)	2.18 (3)	2.672 (3)	118 (2)

Acknowledgements

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

References

Alexakis, A., Tomassini, A., Chouillet, C., Roland, S., Mangeney, P. & Bernardinelli, G. (2000). Angew. Chem. Int. Ed. 39, 4093–4095. CrossRef CAS Google Scholar
Alvaro, J., Grepioni, F. & Savoia, D. (1997). J. Org. Chem. 62, 4180–4182. CSD CrossRef CAS Google Scholar
Bambridge, K., Begley, M. J. & Simpkins, N. S. (1994). Tetrahedron Lett. 35, 3391–3394. CSD CrossRef CAS Web of Science Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Lucet, D., Le Gall, T. & Mioskowski, C. (1998). Angew. Chem. Int. Ed. 37, 2580–2627. CrossRef CAS Google Scholar
Roland, S. & Mangeney, P. (2000). Eur. J. Org. Chem. pp. 611–616. CrossRef Google Scholar
Roland, S., Mangeney, P. & Alexakis, A. (1999). Synthesis, 2, 228–230. CrossRef Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1994). XSCANS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin USA. Google Scholar
Sun, X.-X., Wang, S.-J., Zhu, J. & Deng, J.-G. (2005). Synlett, 18, 2776–2781. Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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