(S,2S,3S)-2-(2-Methyl-propan-2-sulfin-amido)-3-phenyl-butyronitrile.

The absolute configuration has been determined for the title compound, C(14)H(20)N(2)OS. There are two independent mol-ecules in the asymmetric unit. Inter-molecular N-H⋯O hydrogen bonds are observed in the crystal packing, forming infinite chains with the base vectors [100] and [010]. Each chain contains only one of the two independent mol-ecules.

Related literature

For uses of tert-butane­sulfinimines, see: Ferreira et al. (2009 ▶). For asymmetric Strecker reactions utilizing this auxiliary, see: Davis et al. (1994 ▶); Li et al. (2003 ▶). For natural sources of (2S,3S)-β-methyl­phenyl­alanine, see: Singh et al. (2003 ▶); Kaneda (1992 ▶, 2002 ▶). For a related structure, see: Harms et al. (2009 ▶).

Experimental

Crystal data

C14H20N2OS

M = 264.38

Orthorhombic,

a = 9.0344 (4) Å

b = 9.0617 (5) Å

c = 35.767 (3) Å

V = 2928.1 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.21 mm−1

T = 100 K

0.36 × 0.08 × 0.06 mm

Data collection

Stoe IPDS II diffractometer

Absorption correction: multi-scan (Blessing, 1995 ▶) T min = 0.936, T max = 1.041

15474 measured reflections

5160 independent reflections

3413 reflections with I > 2σ(I)

R int = 0.093

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.074

S = 0.77

5160 reflections

342 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.24 e Å−3

Absolute structure: Flack (1983 ▶), 2183 Friedel pairs

Flack parameter: −0.04 (9)

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: publCIF (Westrip, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809041245/pv2213sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809041245/pv2213Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C14H20N2OS	F(000) = 1136
Mr = 264.38	Dx = 1.199 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 10131 reflections
a = 9.0344 (4) Å	θ = 2.3–25°
b = 9.0617 (5) Å	µ = 0.21 mm−1
c = 35.767 (3) Å	T = 100 K
V = 2928.1 (3) Å3	Prism, colourless
Z = 8	0.36 × 0.08 × 0.06 mm

Stoe IPDS II diffractometer	5160 independent reflections
Radiation source: sealed tube	3413 reflections with I > 2σ(I)
graphite	Rint = 0.093
area detetor, ω scans	θmax = 25°, θmin = 2.3°
Absorption correction: multi-scan (Blessing, 1995)	h = −10→10
Tmin = 0.936, Tmax = 1.041	k = −9→10
15474 measured reflections	l = −41→42

Refinement on F2	Hydrogen site location: CH inferred from neighbouring sites, NH located
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.046	w = 1/[σ2(Fo2) + (0.0105P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.074	(Δ/σ)max < 0.001
S = 0.77	Δρmax = 0.19 e Å−3
5160 reflections	Δρmin = −0.24 e Å−3
342 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008)
2 restraints	Extinction coefficient: 0.0011 (3)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 2183 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: −0.04 (9)

Experimental. νmax/cm-1 3232 (br), 2963 (w), 2930 (w), 2872(w), 1492 (w), 1454 (m), 1422 (m), 1364 (w), 1113 (w), 1085 (m), 1054 (s), 1016(m); δH (300 MHz; DMSO) 0.75 (s, 9H, tBu), 1.37 (d, 3H, 3JMe,CH = 7.1 Hz, CH3), 3.10 (dq, 1H, 3JCH,CHN = 10.3, JCH,Me = 7.1 Hz, CH), 4.51 (pt, 1H, 3JCHN,CH = 10.3 Hz, CHN), 6.24 (d, 1H, 3JNH,CHN = 10.5 Hz, NH), 7.14 – 7.32 (m, 5H, CHarom); δC (75 MHz; DMSO-d6)18.4 (CH3), 21.9 (C(CH3)3), 43.2 (CH), 52.8 (CHN), 55.9 (C(CH3)3), 120.2 (CN), 126.7 (p-CHarom), 127.7 (CHarom), 128.2 (CHarom), 141.9 (i-Carom); [α]D23 -1.0 (c 1.00 in CHCl3).

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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.

	x	y	z	Uiso*/Ueq
C21	0.2714 (4)	0.3582 (4)	0.27085 (9)	0.0236 (9)
H21	0.36	0.2946	0.2662	0.028*
C22	0.3222 (4)	0.5196 (4)	0.27258 (10)	0.0270 (9)
H22	0.232	0.5812	0.2769	0.032*
C23	0.2020 (4)	0.3113 (5)	0.30640 (10)	0.0288 (9)
C24	0.4285 (4)	0.5485 (5)	0.30544 (10)	0.0336 (10)
H24A	0.5189	0.4903	0.302	0.05*
H24B	0.3805	0.5198	0.3289	0.05*
H24C	0.4537	0.6536	0.3063	0.05*
C25	0.3851 (4)	0.5647 (4)	0.23521 (10)	0.0251 (9)
C26	0.3155 (4)	0.6706 (4)	0.21346 (10)	0.0310 (9)
H26	0.229	0.7179	0.2227	0.037*
C27	0.3702 (4)	0.7092 (4)	0.17816 (10)	0.0332 (10)
H27	0.3217	0.783	0.1638	0.04*
C28	0.4935 (4)	0.6406 (4)	0.16434 (11)	0.0354 (11)
H28	0.5303	0.6659	0.1403	0.042*
C29	0.5647 (4)	0.5341 (4)	0.18560 (10)	0.0308 (9)
H29	0.6501	0.4861	0.176	0.037*
C210	0.5117 (4)	0.4971 (4)	0.22081 (11)	0.0265 (9)
H210	0.5622	0.425	0.2353	0.032*
C211	0.0856 (4)	0.2374 (4)	0.17447 (11)	0.0281 (9)
C212	−0.0540 (4)	0.3289 (5)	0.17864 (10)	0.0370 (10)
H21A	−0.1007	0.3413	0.1541	0.056*
H21B	−0.0287	0.4259	0.1889	0.056*
H21C	−0.1227	0.2785	0.1956	0.056*
C213	0.0538 (5)	0.0964 (5)	0.15275 (11)	0.0448 (11)
H21D	−0.0214	0.0386	0.166	0.067*
H21E	0.1449	0.0383	0.1505	0.067*
H21F	0.0175	0.1216	0.1277	0.067*
C214	0.2103 (4)	0.3255 (5)	0.15608 (10)	0.0322 (9)
H21G	0.3006	0.2657	0.1556	0.048*
H21H	0.2283	0.4158	0.1704	0.048*
H21I	0.1817	0.3514	0.1305	0.048*
N21	0.1689 (3)	0.3395 (3)	0.23975 (7)	0.0228 (7)
N22	0.1415 (4)	0.2754 (4)	0.33308 (9)	0.0399 (9)
O21	0.0331 (3)	0.0854 (3)	0.23728 (7)	0.0316 (6)
S21	0.15503 (10)	0.17532 (11)	0.22032 (3)	0.0260 (2)
C1	0.8730 (4)	0.4752 (4)	−0.02331 (10)	0.0228 (8)
H1	0.9404	0.3911	−0.0171	0.027*
C2	0.7114 (3)	0.4153 (4)	−0.02369 (10)	0.0252 (8)
H2	0.6449	0.4999	−0.03	0.03*
C3	0.9145 (4)	0.5311 (4)	−0.06101 (11)	0.0268 (9)
C4	0.6885 (4)	0.2967 (4)	−0.05361 (10)	0.0325 (10)
H4A	0.7481	0.2097	−0.0475	0.049*
H4B	0.7189	0.3354	−0.078	0.049*
H4C	0.5836	0.2691	−0.0545	0.049*
C5	0.6698 (4)	0.3632 (4)	0.01507 (9)	0.0242 (9)
C6	0.5653 (4)	0.4409 (4)	0.03603 (10)	0.0283 (9)
H6	0.5181	0.5254	0.0258	0.034*
C7	0.5311 (4)	0.3941 (5)	0.07186 (10)	0.0320 (9)
H7	0.4586	0.4467	0.0857	0.038*
C8	0.5988 (4)	0.2738 (4)	0.08799 (11)	0.0333 (10)
H8	0.5752	0.2442	0.1128	0.04*
C9	0.7019 (4)	0.1975 (4)	0.06715 (11)	0.0317 (9)
H9	0.7496	0.1139	0.0777	0.038*
C10	0.7372 (4)	0.2407 (4)	0.03095 (11)	0.0297 (9)
H10	0.8079	0.1861	0.017	0.036*
C11	0.9830 (4)	0.6723 (4)	0.07127 (9)	0.0234 (8)
C12	0.8840 (4)	0.8074 (4)	0.06764 (10)	0.0320 (9)
H12A	0.7922	0.78	0.0548	0.048*
H12B	0.9355	0.8836	0.0532	0.048*
H12C	0.8606	0.8456	0.0926	0.048*
C13	0.9020 (4)	0.5441 (4)	0.08954 (11)	0.0317 (10)
H13A	0.8719	0.5721	0.1149	0.047*
H13B	0.9677	0.4582	0.0907	0.047*
H13C	0.814	0.5194	0.0748	0.047*
C14	1.1218 (4)	0.7103 (4)	0.09391 (10)	0.0326 (10)
H14A	1.0935	0.7347	0.1196	0.049*
H14B	1.1717	0.7951	0.0825	0.049*
H14C	1.189	0.6254	0.0941	0.049*
N1	0.8892 (3)	0.5844 (3)	0.00524 (8)	0.0215 (7)
N2	0.9438 (4)	0.5784 (4)	−0.08972 (9)	0.0397 (8)
O1	1.1317 (2)	0.7367 (3)	0.00919 (7)	0.0304 (6)
S1	1.05045 (10)	0.60907 (10)	0.02574 (3)	0.0241 (2)
H211	0.087 (2)	0.384 (4)	0.2437 (9)	0.031 (11)*
H1A	0.831 (3)	0.658 (2)	0.0059 (9)	0.027 (10)*

	U11	U22	U33	U12	U13	U23
C21	0.0206 (18)	0.025 (2)	0.025 (2)	0.0023 (15)	−0.0032 (14)	0.0016 (16)
C22	0.023 (2)	0.027 (2)	0.031 (2)	0.0031 (16)	−0.0027 (16)	−0.0024 (17)
C23	0.029 (2)	0.030 (2)	0.027 (2)	0.0060 (18)	0.0026 (17)	0.001 (2)
C24	0.030 (2)	0.039 (3)	0.032 (2)	−0.0029 (19)	−0.0009 (18)	−0.0053 (18)
C25	0.027 (2)	0.021 (2)	0.0267 (19)	−0.0030 (16)	−0.0063 (16)	0.0001 (16)
C26	0.024 (2)	0.026 (2)	0.043 (2)	−0.0047 (18)	−0.0068 (16)	−0.002 (2)
C27	0.041 (2)	0.029 (2)	0.030 (2)	−0.0087 (19)	−0.0113 (19)	0.0050 (18)
C28	0.036 (2)	0.040 (3)	0.031 (2)	−0.0128 (19)	−0.0006 (17)	−0.0053 (19)
C29	0.026 (2)	0.026 (2)	0.041 (2)	−0.0049 (18)	0.0029 (19)	−0.0031 (18)
C210	0.019 (2)	0.022 (2)	0.038 (2)	−0.0009 (15)	−0.0020 (17)	0.0003 (19)
C211	0.025 (2)	0.029 (2)	0.031 (2)	−0.0043 (17)	0.0041 (16)	0.0008 (17)
C212	0.031 (2)	0.041 (2)	0.039 (2)	0.003 (2)	0.0036 (18)	0.015 (2)
C213	0.048 (2)	0.038 (3)	0.049 (3)	−0.016 (2)	−0.004 (2)	−0.002 (2)
C214	0.029 (2)	0.033 (2)	0.035 (2)	−0.0036 (19)	0.0043 (16)	0.004 (2)
N21	0.0181 (17)	0.0239 (17)	0.0263 (15)	0.0025 (14)	−0.0009 (13)	−0.0021 (14)
N22	0.039 (2)	0.038 (2)	0.043 (2)	0.0162 (17)	0.0033 (18)	0.0054 (17)
O21	0.0292 (14)	0.0269 (15)	0.0386 (15)	−0.0126 (12)	0.0023 (11)	0.0106 (13)
S21	0.0233 (5)	0.0241 (5)	0.0306 (5)	−0.0019 (4)	0.0000 (4)	0.0011 (4)
C1	0.0180 (18)	0.0209 (19)	0.030 (2)	0.0025 (14)	0.0008 (16)	0.0009 (17)
C2	0.0179 (18)	0.030 (2)	0.0282 (19)	−0.0001 (15)	−0.0006 (15)	−0.0043 (19)
C3	0.016 (2)	0.033 (2)	0.032 (2)	0.0072 (16)	−0.0033 (16)	−0.0015 (18)
C4	0.023 (2)	0.040 (3)	0.035 (2)	−0.0018 (17)	−0.0022 (16)	−0.005 (2)
C5	0.0168 (18)	0.026 (2)	0.030 (2)	−0.0042 (16)	−0.0004 (15)	−0.0012 (16)
C6	0.0199 (19)	0.027 (2)	0.038 (2)	−0.0019 (17)	−0.0033 (17)	−0.0041 (17)
C7	0.027 (2)	0.037 (2)	0.032 (2)	−0.010 (2)	0.0006 (17)	−0.002 (2)
C8	0.028 (2)	0.040 (3)	0.032 (2)	−0.0152 (18)	0.0005 (17)	0.004 (2)
C9	0.031 (2)	0.024 (2)	0.041 (2)	−0.0078 (17)	−0.0058 (17)	0.005 (2)
C10	0.0200 (19)	0.028 (2)	0.041 (2)	−0.0025 (16)	0.0004 (18)	−0.0013 (19)
C11	0.026 (2)	0.0224 (19)	0.0222 (19)	−0.0018 (16)	0.0003 (14)	−0.0002 (17)
C12	0.036 (2)	0.029 (2)	0.031 (2)	−0.0051 (18)	0.0019 (16)	−0.0009 (19)
C13	0.029 (2)	0.035 (2)	0.031 (2)	−0.0019 (17)	0.0029 (17)	0.0009 (19)
C14	0.026 (2)	0.035 (3)	0.037 (2)	−0.0069 (17)	−0.0029 (17)	−0.0021 (19)
N1	0.0145 (16)	0.0214 (18)	0.0287 (16)	0.0009 (13)	−0.0041 (12)	−0.0014 (14)
N2	0.0345 (19)	0.044 (2)	0.041 (2)	0.0121 (17)	0.0020 (17)	0.0041 (18)
O1	0.0252 (13)	0.0318 (15)	0.0342 (15)	−0.0099 (12)	0.0069 (12)	0.0021 (12)
S1	0.0194 (4)	0.0229 (5)	0.0300 (5)	−0.0018 (4)	−0.0001 (4)	−0.0006 (5)

C21—N21	1.457 (4)	C1—N1	1.429 (4)
C21—C23	1.480 (5)	C1—C3	1.488 (5)
C21—C22	1.535 (5)	C1—C2	1.557 (4)
C21—H21	1	C1—H1	1
C22—C25	1.509 (5)	C2—C5	1.512 (5)
C22—C24	1.540 (5)	C2—C4	1.530 (5)
C22—H22	1	C2—H2	1
C23—N22	1.146 (4)	C3—N2	1.144 (4)
C24—H24A	0.98	C4—H4A	0.98
C24—H24B	0.98	C4—H4B	0.98
C24—H24C	0.98	C4—H4C	0.98
C25—C26	1.386 (5)	C5—C10	1.387 (5)
C25—C210	1.396 (5)	C5—C6	1.396 (5)
C26—C27	1.400 (5)	C6—C7	1.385 (5)
C26—H26	0.95	C6—H6	0.95
C27—C28	1.369 (5)	C7—C8	1.377 (5)
C27—H27	0.95	C7—H7	0.95
C28—C29	1.387 (5)	C8—C9	1.379 (5)
C28—H28	0.95	C8—H8	0.95
C29—C210	1.388 (5)	C9—C10	1.390 (5)
C29—H29	0.95	C9—H9	0.95
C210—H210	0.95	C10—H10	0.95
C211—C212	1.516 (5)	C11—C13	1.520 (5)
C211—C213	1.523 (5)	C11—C12	1.522 (5)
C211—C214	1.529 (5)	C11—C14	1.532 (4)
C211—S21	1.843 (4)	C11—S1	1.831 (3)
C212—H21A	0.98	C12—H12A	0.98
C212—H21B	0.98	C12—H12B	0.98
C212—H21C	0.98	C12—H12C	0.98
C213—H21D	0.98	C13—H13A	0.98
C213—H21E	0.98	C13—H13B	0.98
C213—H21F	0.98	C13—H13C	0.98
C214—H21G	0.98	C14—H14A	0.98
C214—H21H	0.98	C14—H14B	0.98
C214—H21I	0.98	C14—H14C	0.98
N21—S21	1.647 (3)	N1—S1	1.646 (3)
N21—H211	0.85 (2)	N1—H1A	0.85 (2)
O21—S21	1.498 (2)	O1—S1	1.493 (2)
N21—C21—C23	110.7 (3)	N1—C1—C3	112.7 (3)
N21—C21—C22	109.4 (3)	N1—C1—C2	110.1 (3)
C23—C21—C22	111.5 (3)	C3—C1—C2	110.3 (3)
N21—C21—H21	108.4	N1—C1—H1	107.9
C23—C21—H21	108.4	C3—C1—H1	107.9
C22—C21—H21	108.4	C2—C1—H1	107.9
C25—C22—C21	109.6 (3)	C5—C2—C4	112.8 (3)
C25—C22—C24	113.3 (3)	C5—C2—C1	109.5 (3)
C21—C22—C24	112.3 (3)	C4—C2—C1	112.2 (3)
C25—C22—H22	107.1	C5—C2—H2	107.3
C21—C22—H22	107.1	C4—C2—H2	107.3
C24—C22—H22	107.1	C1—C2—H2	107.3
N22—C23—C21	176.6 (4)	N2—C3—C1	177.7 (4)
C22—C24—H24A	109.5	C2—C4—H4A	109.5
C22—C24—H24B	109.5	C2—C4—H4B	109.5
H24A—C24—H24B	109.5	H4A—C4—H4B	109.5
C22—C24—H24C	109.5	C2—C4—H4C	109.5
H24A—C24—H24C	109.5	H4A—C4—H4C	109.5
H24B—C24—H24C	109.5	H4B—C4—H4C	109.5
C26—C25—C210	117.9 (4)	C10—C5—C6	118.7 (3)
C26—C25—C22	120.9 (3)	C10—C5—C2	121.1 (3)
C210—C25—C22	121.1 (3)	C6—C5—C2	120.2 (3)
C25—C26—C27	121.3 (4)	C7—C6—C5	119.6 (4)
C25—C26—H26	119.4	C7—C6—H6	120.2
C27—C26—H26	119.4	C5—C6—H6	120.2
C28—C27—C26	120.0 (4)	C8—C7—C6	122.1 (4)
C28—C27—H27	120	C8—C7—H7	119
C26—C27—H27	120	C6—C7—H7	119
C27—C28—C29	119.7 (4)	C7—C8—C9	118.1 (4)
C27—C28—H28	120.1	C7—C8—H8	121
C29—C28—H28	120.1	C9—C8—H8	121
C28—C29—C210	120.4 (4)	C8—C9—C10	121.1 (4)
C28—C29—H29	119.8	C8—C9—H9	119.4
C210—C29—H29	119.8	C10—C9—H9	119.4
C29—C210—C25	120.8 (4)	C5—C10—C9	120.4 (4)
C29—C210—H210	119.6	C5—C10—H10	119.8
C25—C210—H210	119.6	C9—C10—H10	119.8
C212—C211—C213	110.6 (3)	C13—C11—C12	111.6 (3)
C212—C211—C214	111.7 (3)	C13—C11—C14	109.8 (3)
C213—C211—C214	110.9 (3)	C12—C11—C14	110.2 (3)
C212—C211—S21	111.2 (2)	C13—C11—S1	107.7 (3)
C213—C211—S21	105.2 (3)	C12—C11—S1	111.8 (2)
C214—C211—S21	107.0 (2)	C14—C11—S1	105.5 (2)
C211—C212—H21A	109.5	C11—C12—H12A	109.5
C211—C212—H21B	109.5	C11—C12—H12B	109.5
H21A—C212—H21B	109.5	H12A—C12—H12B	109.5
C211—C212—H21C	109.5	C11—C12—H12C	109.5
H21A—C212—H21C	109.5	H12A—C12—H12C	109.5
H21B—C212—H21C	109.5	H12B—C12—H12C	109.5
C211—C213—H21D	109.5	C11—C13—H13A	109.5
C211—C213—H21E	109.5	C11—C13—H13B	109.5
H21D—C213—H21E	109.5	H13A—C13—H13B	109.5
C211—C213—H21F	109.5	C11—C13—H13C	109.5
H21D—C213—H21F	109.5	H13A—C13—H13C	109.5
H21E—C213—H21F	109.5	H13B—C13—H13C	109.5
C211—C214—H21G	109.5	C11—C14—H14A	109.5
C211—C214—H21H	109.5	C11—C14—H14B	109.5
H21G—C214—H21H	109.5	H14A—C14—H14B	109.5
C211—C214—H21I	109.5	C11—C14—H14C	109.5
H21G—C214—H21I	109.5	H14A—C14—H14C	109.5
H21H—C214—H21I	109.5	H14B—C14—H14C	109.5
C21—N21—S21	118.4 (2)	C1—N1—S1	120.2 (2)
C21—N21—H211	112 (2)	C1—N1—H1A	120 (2)
S21—N21—H211	115 (3)	S1—N1—H1A	115 (2)
O21—S21—N21	112.12 (15)	O1—S1—N1	111.33 (15)
O21—S21—C211	106.03 (15)	O1—S1—C11	105.92 (16)
N21—S21—C211	97.20 (16)	N1—S1—C11	98.29 (15)
N21—C21—C22—C25	−54.4 (4)	N1—C1—C2—C5	−53.4 (4)
C23—C21—C22—C25	−177.1 (3)	C3—C1—C2—C5	−178.3 (3)
N21—C21—C22—C24	178.7 (3)	N1—C1—C2—C4	−179.5 (3)
C23—C21—C22—C24	56.0 (4)	C3—C1—C2—C4	55.6 (4)
N21—C21—C23—N22	−17 (8)	N1—C1—C3—N2	−44 (10)
C22—C21—C23—N22	105 (7)	C2—C1—C3—N2	80 (10)
C21—C22—C25—C26	114.1 (4)	C4—C2—C5—C10	58.2 (4)
C24—C22—C25—C26	−119.7 (4)	C1—C2—C5—C10	−67.5 (4)
C21—C22—C25—C210	−63.4 (4)	C4—C2—C5—C6	−123.8 (3)
C24—C22—C25—C210	62.8 (4)	C1—C2—C5—C6	110.4 (3)
C210—C25—C26—C27	−0.1 (5)	C10—C5—C6—C7	−0.3 (5)
C22—C25—C26—C27	−177.7 (3)	C2—C5—C6—C7	−178.3 (3)
C25—C26—C27—C28	0.8 (5)	C5—C6—C7—C8	1.1 (5)
C26—C27—C28—C29	−0.6 (5)	C6—C7—C8—C9	−1.1 (5)
C27—C28—C29—C210	−0.2 (5)	C7—C8—C9—C10	0.2 (5)
C28—C29—C210—C25	0.9 (5)	C6—C5—C10—C9	−0.5 (5)
C26—C25—C210—C29	−0.8 (5)	C2—C5—C10—C9	177.5 (3)
C22—C25—C210—C29	176.8 (3)	C8—C9—C10—C5	0.5 (5)
C23—C21—N21—S21	−83.2 (3)	C3—C1—N1—S1	−85.7 (3)
C22—C21—N21—S21	153.6 (2)	C2—C1—N1—S1	150.7 (2)
C21—N21—S21—O21	93.0 (3)	C1—N1—S1—O1	98.6 (3)
C21—N21—S21—C211	−156.4 (2)	C1—N1—S1—C11	−150.6 (3)
C212—C211—S21—O21	59.6 (3)	C13—C11—S1—O1	−178.8 (2)
C213—C211—S21—O21	−60.2 (3)	C12—C11—S1—O1	58.2 (3)
C214—C211—S21—O21	−178.2 (2)	C14—C11—S1—O1	−61.6 (3)
C212—C211—S21—N21	−56.0 (3)	C13—C11—S1—N1	66.1 (3)
C213—C211—S21—N21	−175.7 (2)	C12—C11—S1—N1	−56.9 (3)
C214—C211—S21—N21	66.2 (3)	C14—C11—S1—N1	−176.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.85 (2)	2.11 (2)	2.882 (3)	151 (3)
N21—H211···O21ii	0.85 (2)	2.23 (2)	2.995 (4)	149 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.85 (2)	2.110 (17)	2.882 (3)	151 (3)
N21—H211⋯O21ii	0.85 (2)	2.23 (2)	2.995 (4)	149 (3)

Symmetry codes: (i) ; (ii) .