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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2742.
Published online 2009 October 17. doi:  10.1107/S1600536809041245
PMCID: PMC2971363

(S S,2S,3S)-2-(2-Methyl­propan-2-sulfin­amido)-3-phenyl­butyronitrile

Abstract

The absolute configuration has been determined for the title compound, C14H20N2OS. There are two independent mol­ecules in the asymmetric unit. Inter­molecular 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 mol­ecules.

Related literature

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

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Object name is e-65-o2742-scheme1.jpg

Experimental

Crystal data

  • C14H20N2OS
  • M r = 264.38
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2742-efi5.jpg
  • 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 [triangle]) 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 [triangle]), 2183 Friedel pairs
  • Flack parameter: −0.04 (9)

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Acknowledgments

The authors gratefully acknowledge funding by the Philipps-Universität Marburg, the Deutsche Forschungsgemeinschaft (PS & MO) and the Ernst-Schering-Foundation (PS).

supplementary crystallographic information

Comment

Chiral sulfinimines have proven to be powerful and versatile precursors for the synthesis of nonproteinogenic amino acids (Ferreira et al., 2008). They allow the stereoselective introduction of cyanide therefore representing an asymmetric modification of the Strecker reaction (Davis et al., 1994); Li et al., 2003). We have synthesized the title compound, (I), that can be hydrolyzed to give (2S,3S)-β-methylphenylalanine which is an amino acid found in the antibiotic families of the bottromycins and the mannopeptimycins (Singh et al., 2003); Kaneda, 1992; and Kaneda, 2002). In this paper we report the crystal structure and absolute configuration of (I).

The molecular structure of (I) is presented in Fig. 1. There are two independent molecules in the asymmetric unit. The structure exhibits intermolecular N—H···O hydrogen bonds resulting in infinite one dimensional chains with the base vectors [1 0 0] and [0 1 0], respectively (details have have been provided in Table 1 and Fig. 2). Each chain contains only one of the two independent molecules.

The crystal structure and absolute configuration of a closely related compound has just been reported (Harms et al., 2009).

Experimental

Trimethylsilyl cyanide (TMSCN) (706 µL, 5.64 mmol) was added dropwise to a solution of (SS)-(2-phenylpropyliden)-2-methyl-2-propansulfinylimin (1.12 g, 4.70 mmol) and CsF (858 mg, 5.64 mmol) in 50 ml n-hexane at 243 K. The mixture was stirred at this temperature for 14 h and subsequently quenched with semisaturated aqueous NH4Cl solution. Extraction with EtOAc (2×50 mL) and drying of the combined organic phases (MgSO4) yielded the crude mixture of 3S / 3R epimers. Crystallization from petrolether/EtOAc yielded 370 mg (1.41 mmol, 35%) of a 1:1 mixture of the diastereomers. Flash column chromatography of the mother liquor yielded 80 mg (303 mmol, 6%) of the pure 3S isomer, which had a slightly higher Rf-value (Rf=0.30 in petrol ether/EtOAc 2:1) than the 3R isomer of which 60 mg (227 mmol, 5%) could be isolated. The remaining fractions afforded 400 mg (1.53 mmol, 32%) of a roughly 1:1 mixture of the epimers. (SS,2S,3S)-(2-Methylpropansulfinyl)-2-amino-3-phenylbutyronitrile was crystallized from petrol ether/THF.

Refinement

The amino H atoms were isotropically refined with a restraint (0.85 Å) N—H distance. The other H atoms were positioned geometrically (C—H = 0.95–1.00 Å) and allowed to ride on their parent atoms, with 1.5 Ueq(Cmethyl) or 1.2 Ueq(C).

Figures

Fig. 1.
A view of the two molecules in the asymmetric unit of (I). Displacement ellipsoids are drawn at the 50% probability level. Symmetry operations, (i): x-1/2, -y+3/2, -z; (ii): -x, y+1/2, -z+1/2.
Fig. 2.
Unit cell packing of (I) viewed down the b-axis. Dotted lines indicate hydrogen bonds.

Crystal data

C14H20N2OSF(000) = 1136
Mr = 264.38Dx = 1.199 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 10131 reflections
a = 9.0344 (4) Åθ = 2.3–25°
b = 9.0617 (5) ŵ = 0.21 mm1
c = 35.767 (3) ÅT = 100 K
V = 2928.1 (3) Å3Prism, colourless
Z = 80.36 × 0.08 × 0.06 mm

Data collection

Stoe IPDS II diffractometer5160 independent reflections
Radiation source: sealed tube3413 reflections with I > 2σ(I)
graphiteRint = 0.093
area detetor, ω scansθmax = 25°, θmin = 2.3°
Absorption correction: multi-scan (Blessing, 1995)h = −10→10
Tmin = 0.936, Tmax = 1.041k = −9→10
15474 measured reflectionsl = −41→42

Refinement

Refinement on F2Hydrogen site location: CH inferred from neighbouring sites, NH located
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.046w = 1/[σ2(Fo2) + (0.0105P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.074(Δ/σ)max < 0.001
S = 0.77Δρmax = 0.19 e Å3
5160 reflectionsΔρmin = −0.24 e Å3
342 parametersExtinction correction: SHELXL97 (Sheldrick, 2008)
2 restraintsExtinction coefficient: 0.0011 (3)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 2183 Friedel pairs
Secondary atom site location: difference Fourier mapFlack parameter: −0.04 (9)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
C210.2714 (4)0.3582 (4)0.27085 (9)0.0236 (9)
H210.360.29460.26620.028*
C220.3222 (4)0.5196 (4)0.27258 (10)0.0270 (9)
H220.2320.58120.27690.032*
C230.2020 (4)0.3113 (5)0.30640 (10)0.0288 (9)
C240.4285 (4)0.5485 (5)0.30544 (10)0.0336 (10)
H24A0.51890.49030.3020.05*
H24B0.38050.51980.32890.05*
H24C0.45370.65360.30630.05*
C250.3851 (4)0.5647 (4)0.23521 (10)0.0251 (9)
C260.3155 (4)0.6706 (4)0.21346 (10)0.0310 (9)
H260.2290.71790.22270.037*
C270.3702 (4)0.7092 (4)0.17816 (10)0.0332 (10)
H270.32170.7830.16380.04*
C280.4935 (4)0.6406 (4)0.16434 (11)0.0354 (11)
H280.53030.66590.14030.042*
C290.5647 (4)0.5341 (4)0.18560 (10)0.0308 (9)
H290.65010.48610.1760.037*
C2100.5117 (4)0.4971 (4)0.22081 (11)0.0265 (9)
H2100.56220.4250.23530.032*
C2110.0856 (4)0.2374 (4)0.17447 (11)0.0281 (9)
C212−0.0540 (4)0.3289 (5)0.17864 (10)0.0370 (10)
H21A−0.10070.34130.15410.056*
H21B−0.02870.42590.18890.056*
H21C−0.12270.27850.19560.056*
C2130.0538 (5)0.0964 (5)0.15275 (11)0.0448 (11)
H21D−0.02140.03860.1660.067*
H21E0.14490.03830.15050.067*
H21F0.01750.12160.12770.067*
C2140.2103 (4)0.3255 (5)0.15608 (10)0.0322 (9)
H21G0.30060.26570.15560.048*
H21H0.22830.41580.17040.048*
H21I0.18170.35140.13050.048*
N210.1689 (3)0.3395 (3)0.23975 (7)0.0228 (7)
N220.1415 (4)0.2754 (4)0.33308 (9)0.0399 (9)
O210.0331 (3)0.0854 (3)0.23728 (7)0.0316 (6)
S210.15503 (10)0.17532 (11)0.22032 (3)0.0260 (2)
C10.8730 (4)0.4752 (4)−0.02331 (10)0.0228 (8)
H10.94040.3911−0.01710.027*
C20.7114 (3)0.4153 (4)−0.02369 (10)0.0252 (8)
H20.64490.4999−0.030.03*
C30.9145 (4)0.5311 (4)−0.06101 (11)0.0268 (9)
C40.6885 (4)0.2967 (4)−0.05361 (10)0.0325 (10)
H4A0.74810.2097−0.04750.049*
H4B0.71890.3354−0.0780.049*
H4C0.58360.2691−0.05450.049*
C50.6698 (4)0.3632 (4)0.01507 (9)0.0242 (9)
C60.5653 (4)0.4409 (4)0.03603 (10)0.0283 (9)
H60.51810.52540.02580.034*
C70.5311 (4)0.3941 (5)0.07186 (10)0.0320 (9)
H70.45860.44670.08570.038*
C80.5988 (4)0.2738 (4)0.08799 (11)0.0333 (10)
H80.57520.24420.11280.04*
C90.7019 (4)0.1975 (4)0.06715 (11)0.0317 (9)
H90.74960.11390.07770.038*
C100.7372 (4)0.2407 (4)0.03095 (11)0.0297 (9)
H100.80790.18610.0170.036*
C110.9830 (4)0.6723 (4)0.07127 (9)0.0234 (8)
C120.8840 (4)0.8074 (4)0.06764 (10)0.0320 (9)
H12A0.79220.780.05480.048*
H12B0.93550.88360.05320.048*
H12C0.86060.84560.09260.048*
C130.9020 (4)0.5441 (4)0.08954 (11)0.0317 (10)
H13A0.87190.57210.11490.047*
H13B0.96770.45820.09070.047*
H13C0.8140.51940.07480.047*
C141.1218 (4)0.7103 (4)0.09391 (10)0.0326 (10)
H14A1.09350.73470.11960.049*
H14B1.17170.79510.08250.049*
H14C1.1890.62540.09410.049*
N10.8892 (3)0.5844 (3)0.00524 (8)0.0215 (7)
N20.9438 (4)0.5784 (4)−0.08972 (9)0.0397 (8)
O11.1317 (2)0.7367 (3)0.00919 (7)0.0304 (6)
S11.05045 (10)0.60907 (10)0.02574 (3)0.0241 (2)
H2110.087 (2)0.384 (4)0.2437 (9)0.031 (11)*
H1A0.831 (3)0.658 (2)0.0059 (9)0.027 (10)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C210.0206 (18)0.025 (2)0.025 (2)0.0023 (15)−0.0032 (14)0.0016 (16)
C220.023 (2)0.027 (2)0.031 (2)0.0031 (16)−0.0027 (16)−0.0024 (17)
C230.029 (2)0.030 (2)0.027 (2)0.0060 (18)0.0026 (17)0.001 (2)
C240.030 (2)0.039 (3)0.032 (2)−0.0029 (19)−0.0009 (18)−0.0053 (18)
C250.027 (2)0.021 (2)0.0267 (19)−0.0030 (16)−0.0063 (16)0.0001 (16)
C260.024 (2)0.026 (2)0.043 (2)−0.0047 (18)−0.0068 (16)−0.002 (2)
C270.041 (2)0.029 (2)0.030 (2)−0.0087 (19)−0.0113 (19)0.0050 (18)
C280.036 (2)0.040 (3)0.031 (2)−0.0128 (19)−0.0006 (17)−0.0053 (19)
C290.026 (2)0.026 (2)0.041 (2)−0.0049 (18)0.0029 (19)−0.0031 (18)
C2100.019 (2)0.022 (2)0.038 (2)−0.0009 (15)−0.0020 (17)0.0003 (19)
C2110.025 (2)0.029 (2)0.031 (2)−0.0043 (17)0.0041 (16)0.0008 (17)
C2120.031 (2)0.041 (2)0.039 (2)0.003 (2)0.0036 (18)0.015 (2)
C2130.048 (2)0.038 (3)0.049 (3)−0.016 (2)−0.004 (2)−0.002 (2)
C2140.029 (2)0.033 (2)0.035 (2)−0.0036 (19)0.0043 (16)0.004 (2)
N210.0181 (17)0.0239 (17)0.0263 (15)0.0025 (14)−0.0009 (13)−0.0021 (14)
N220.039 (2)0.038 (2)0.043 (2)0.0162 (17)0.0033 (18)0.0054 (17)
O210.0292 (14)0.0269 (15)0.0386 (15)−0.0126 (12)0.0023 (11)0.0106 (13)
S210.0233 (5)0.0241 (5)0.0306 (5)−0.0019 (4)0.0000 (4)0.0011 (4)
C10.0180 (18)0.0209 (19)0.030 (2)0.0025 (14)0.0008 (16)0.0009 (17)
C20.0179 (18)0.030 (2)0.0282 (19)−0.0001 (15)−0.0006 (15)−0.0043 (19)
C30.016 (2)0.033 (2)0.032 (2)0.0072 (16)−0.0033 (16)−0.0015 (18)
C40.023 (2)0.040 (3)0.035 (2)−0.0018 (17)−0.0022 (16)−0.005 (2)
C50.0168 (18)0.026 (2)0.030 (2)−0.0042 (16)−0.0004 (15)−0.0012 (16)
C60.0199 (19)0.027 (2)0.038 (2)−0.0019 (17)−0.0033 (17)−0.0041 (17)
C70.027 (2)0.037 (2)0.032 (2)−0.010 (2)0.0006 (17)−0.002 (2)
C80.028 (2)0.040 (3)0.032 (2)−0.0152 (18)0.0005 (17)0.004 (2)
C90.031 (2)0.024 (2)0.041 (2)−0.0078 (17)−0.0058 (17)0.005 (2)
C100.0200 (19)0.028 (2)0.041 (2)−0.0025 (16)0.0004 (18)−0.0013 (19)
C110.026 (2)0.0224 (19)0.0222 (19)−0.0018 (16)0.0003 (14)−0.0002 (17)
C120.036 (2)0.029 (2)0.031 (2)−0.0051 (18)0.0019 (16)−0.0009 (19)
C130.029 (2)0.035 (2)0.031 (2)−0.0019 (17)0.0029 (17)0.0009 (19)
C140.026 (2)0.035 (3)0.037 (2)−0.0069 (17)−0.0029 (17)−0.0021 (19)
N10.0145 (16)0.0214 (18)0.0287 (16)0.0009 (13)−0.0041 (12)−0.0014 (14)
N20.0345 (19)0.044 (2)0.041 (2)0.0121 (17)0.0020 (17)0.0041 (18)
O10.0252 (13)0.0318 (15)0.0342 (15)−0.0099 (12)0.0069 (12)0.0021 (12)
S10.0194 (4)0.0229 (5)0.0300 (5)−0.0018 (4)−0.0001 (4)−0.0006 (5)

Geometric parameters (Å, °)

C21—N211.457 (4)C1—N11.429 (4)
C21—C231.480 (5)C1—C31.488 (5)
C21—C221.535 (5)C1—C21.557 (4)
C21—H211C1—H11
C22—C251.509 (5)C2—C51.512 (5)
C22—C241.540 (5)C2—C41.530 (5)
C22—H221C2—H21
C23—N221.146 (4)C3—N21.144 (4)
C24—H24A0.98C4—H4A0.98
C24—H24B0.98C4—H4B0.98
C24—H24C0.98C4—H4C0.98
C25—C261.386 (5)C5—C101.387 (5)
C25—C2101.396 (5)C5—C61.396 (5)
C26—C271.400 (5)C6—C71.385 (5)
C26—H260.95C6—H60.95
C27—C281.369 (5)C7—C81.377 (5)
C27—H270.95C7—H70.95
C28—C291.387 (5)C8—C91.379 (5)
C28—H280.95C8—H80.95
C29—C2101.388 (5)C9—C101.390 (5)
C29—H290.95C9—H90.95
C210—H2100.95C10—H100.95
C211—C2121.516 (5)C11—C131.520 (5)
C211—C2131.523 (5)C11—C121.522 (5)
C211—C2141.529 (5)C11—C141.532 (4)
C211—S211.843 (4)C11—S11.831 (3)
C212—H21A0.98C12—H12A0.98
C212—H21B0.98C12—H12B0.98
C212—H21C0.98C12—H12C0.98
C213—H21D0.98C13—H13A0.98
C213—H21E0.98C13—H13B0.98
C213—H21F0.98C13—H13C0.98
C214—H21G0.98C14—H14A0.98
C214—H21H0.98C14—H14B0.98
C214—H21I0.98C14—H14C0.98
N21—S211.647 (3)N1—S11.646 (3)
N21—H2110.85 (2)N1—H1A0.85 (2)
O21—S211.498 (2)O1—S11.493 (2)
N21—C21—C23110.7 (3)N1—C1—C3112.7 (3)
N21—C21—C22109.4 (3)N1—C1—C2110.1 (3)
C23—C21—C22111.5 (3)C3—C1—C2110.3 (3)
N21—C21—H21108.4N1—C1—H1107.9
C23—C21—H21108.4C3—C1—H1107.9
C22—C21—H21108.4C2—C1—H1107.9
C25—C22—C21109.6 (3)C5—C2—C4112.8 (3)
C25—C22—C24113.3 (3)C5—C2—C1109.5 (3)
C21—C22—C24112.3 (3)C4—C2—C1112.2 (3)
C25—C22—H22107.1C5—C2—H2107.3
C21—C22—H22107.1C4—C2—H2107.3
C24—C22—H22107.1C1—C2—H2107.3
N22—C23—C21176.6 (4)N2—C3—C1177.7 (4)
C22—C24—H24A109.5C2—C4—H4A109.5
C22—C24—H24B109.5C2—C4—H4B109.5
H24A—C24—H24B109.5H4A—C4—H4B109.5
C22—C24—H24C109.5C2—C4—H4C109.5
H24A—C24—H24C109.5H4A—C4—H4C109.5
H24B—C24—H24C109.5H4B—C4—H4C109.5
C26—C25—C210117.9 (4)C10—C5—C6118.7 (3)
C26—C25—C22120.9 (3)C10—C5—C2121.1 (3)
C210—C25—C22121.1 (3)C6—C5—C2120.2 (3)
C25—C26—C27121.3 (4)C7—C6—C5119.6 (4)
C25—C26—H26119.4C7—C6—H6120.2
C27—C26—H26119.4C5—C6—H6120.2
C28—C27—C26120.0 (4)C8—C7—C6122.1 (4)
C28—C27—H27120C8—C7—H7119
C26—C27—H27120C6—C7—H7119
C27—C28—C29119.7 (4)C7—C8—C9118.1 (4)
C27—C28—H28120.1C7—C8—H8121
C29—C28—H28120.1C9—C8—H8121
C28—C29—C210120.4 (4)C8—C9—C10121.1 (4)
C28—C29—H29119.8C8—C9—H9119.4
C210—C29—H29119.8C10—C9—H9119.4
C29—C210—C25120.8 (4)C5—C10—C9120.4 (4)
C29—C210—H210119.6C5—C10—H10119.8
C25—C210—H210119.6C9—C10—H10119.8
C212—C211—C213110.6 (3)C13—C11—C12111.6 (3)
C212—C211—C214111.7 (3)C13—C11—C14109.8 (3)
C213—C211—C214110.9 (3)C12—C11—C14110.2 (3)
C212—C211—S21111.2 (2)C13—C11—S1107.7 (3)
C213—C211—S21105.2 (3)C12—C11—S1111.8 (2)
C214—C211—S21107.0 (2)C14—C11—S1105.5 (2)
C211—C212—H21A109.5C11—C12—H12A109.5
C211—C212—H21B109.5C11—C12—H12B109.5
H21A—C212—H21B109.5H12A—C12—H12B109.5
C211—C212—H21C109.5C11—C12—H12C109.5
H21A—C212—H21C109.5H12A—C12—H12C109.5
H21B—C212—H21C109.5H12B—C12—H12C109.5
C211—C213—H21D109.5C11—C13—H13A109.5
C211—C213—H21E109.5C11—C13—H13B109.5
H21D—C213—H21E109.5H13A—C13—H13B109.5
C211—C213—H21F109.5C11—C13—H13C109.5
H21D—C213—H21F109.5H13A—C13—H13C109.5
H21E—C213—H21F109.5H13B—C13—H13C109.5
C211—C214—H21G109.5C11—C14—H14A109.5
C211—C214—H21H109.5C11—C14—H14B109.5
H21G—C214—H21H109.5H14A—C14—H14B109.5
C211—C214—H21I109.5C11—C14—H14C109.5
H21G—C214—H21I109.5H14A—C14—H14C109.5
H21H—C214—H21I109.5H14B—C14—H14C109.5
C21—N21—S21118.4 (2)C1—N1—S1120.2 (2)
C21—N21—H211112 (2)C1—N1—H1A120 (2)
S21—N21—H211115 (3)S1—N1—H1A115 (2)
O21—S21—N21112.12 (15)O1—S1—N1111.33 (15)
O21—S21—C211106.03 (15)O1—S1—C11105.92 (16)
N21—S21—C21197.20 (16)N1—S1—C1198.29 (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—C24178.7 (3)N1—C1—C2—C4−179.5 (3)
C23—C21—C22—C2456.0 (4)C3—C1—C2—C455.6 (4)
N21—C21—C23—N22−17 (8)N1—C1—C3—N2−44 (10)
C22—C21—C23—N22105 (7)C2—C1—C3—N280 (10)
C21—C22—C25—C26114.1 (4)C4—C2—C5—C1058.2 (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—C21062.8 (4)C1—C2—C5—C6110.4 (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—C280.8 (5)C5—C6—C7—C81.1 (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—C100.2 (5)
C28—C29—C210—C250.9 (5)C6—C5—C10—C9−0.5 (5)
C26—C25—C210—C29−0.8 (5)C2—C5—C10—C9177.5 (3)
C22—C25—C210—C29176.8 (3)C8—C9—C10—C50.5 (5)
C23—C21—N21—S21−83.2 (3)C3—C1—N1—S1−85.7 (3)
C22—C21—N21—S21153.6 (2)C2—C1—N1—S1150.7 (2)
C21—N21—S21—O2193.0 (3)C1—N1—S1—O198.6 (3)
C21—N21—S21—C211−156.4 (2)C1—N1—S1—C11−150.6 (3)
C212—C211—S21—O2159.6 (3)C13—C11—S1—O1−178.8 (2)
C213—C211—S21—O21−60.2 (3)C12—C11—S1—O158.2 (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—N166.1 (3)
C213—C211—S21—N21−175.7 (2)C12—C11—S1—N1−56.9 (3)
C214—C211—S21—N2166.2 (3)C14—C11—S1—N1−176.7 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.85 (2)2.11 (2)2.882 (3)151 (3)
N21—H211···O21ii0.85 (2)2.23 (2)2.995 (4)149 (3)

Symmetry codes: (i) x−1/2, −y+3/2, −z; (ii) −x, y+1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2213).

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