Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Previous article
Next article
Previous article
Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Next article

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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 70| Part 2| February 2014| Page o153
doi:10.1107/S1600536814000257

rac-2-Phenyl-1-[(2,4,6-triiso­propyl­benzene)­sulfon­yl]aziridine

Christopher Golz,a Hans Preuta and Carsten Strohmanna*

aFakultät für Chemie und Chemische Biologie, Technische Universität Dortmund, Otto-Hahn-Strasse 6, 44221 Dortmund, Germany
*Correspondence e-mail: carsten.strohmann@tu-dortmund.de

(Received 9 December 2013; accepted 6 January 2014; online 15 January 2014)

In the title compound, C23H31NO2S, the geometry of the triiso­propyl­phenyl group is slightly distorted, with elongated C—C bonds at the ipso-C atom, and an S atom which deviates from the benzene ring plane by 0.228 (2) Å. This distortion is caused by the bulky substituents and, in comparison, an unbent geometry is observed in N-toluene­sulfonyl­aziridine [Zhu et al. (2006[Zhu, J., Zhang, M.-J., Liu, Q.-W. & Pan, Z.-H. (2006). Acta Cryst. E62, o1507-o1508.]). Acta Cryst. E62, o1507–o1508]. π–π inter­actions between adjacent benzene rings [centroid–centroid distance = 3.7928 (11) Å] and are observed.

CCDC reference: 979593

Related literature

For structures containing the triiso­propyl­benzene­sulfonyl group with detailed discussion of the geometry, see: Sandrock et al. (2004[Sandrock, P. B., Meyers, C. Y., Rath, N. P. & Robinson, P. D. (2004). Acta Cryst. E60, o544-o546.]); Laba et al. (2009[Laba, V. I., Sviridova, A. V. & Nesterov, V. N. (2009). Kristallografiya, 54, 44-47.]). For the li­thia­tion of activated aziridines, see: Huang et al. (2009[Huang, J., Moore, S. P., O'Brien, P., Whitwood, A. C. & Gilday, J. (2009). Org. Biomol. Chem. 7, 335-345.]) and for a general review on aziridinylanions, see: Florio & Luisi (2010[Florio, S. & Luisi, R. (2010). Chem. Rec. 110, 5128-5157.]). For the most recent synthesis of the title compound, see: Kavanagh et al. (2013[Kavanagh, S. A., Piccini, A. & Connon, S. J. (2013). Org. Biomol. Chem. 11, 3535-3540.]). For deprotonation reactions of aziridinyl anions to amines, see: Gessner & Strohmann (2007[Gessner, V. H. & Strohmann, C. (2007). Angew. Chem. Int. Ed. 46, 4566-4569.], 2008a[Gessner, V. H. & Strohmann, C. (2008a). Angew. Chem. Int. Ed. 46, 8281-8283.],b[Gessner, V. H. & Strohmann, C. (2008b). J. Am. Chem. Soc. 130, 14412-14413.]); Unkelbach et al. (2012[Unkelbach, C., Rosenbaum, H. S. & Strohmann, C. (2012). Chem. Commun. 48, 10612-10614.]).

[Scheme 1]

Experimental

Crystal data

  • C23H31NO2S

  • Mr = 385.55

  • Triclinic, [P \overline 1]

  • a = 6.3037 (3) Å

  • b = 9.6995 (5) Å

  • c = 18.6675 (9) Å

  • α = 75.280 (4)°

  • β = 86.842 (4)°

  • γ = 84.404 (4)°

  • V = 1098.11 (10) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.16 mm−1

  • T = 173 K

  • 0.31 × 0.05 × 0.04 mm
Data collection

  • Agilent Xcalibur Sapphire3 diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2012[Oxford Diffraction (2012). CrysAlis CCD, CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]) Tmin = 0.952, Tmax = 1.000

  • 17550 measured reflections

  • 4314 independent reflections

  • 3633 reflections with I > 2σ(I)

  • Rint = 0.045
Refinement

  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 0.107

  • S = 1.06

  • 4314 reflections

  • 250 parameters

  • H-atom parameters constrained

  • Δρmax = 0.34 e Å−3

  • Δρmin = −0.35 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2012[Oxford Diffraction (2012). CrysAlis CCD, CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2012[Oxford Diffraction (2012). CrysAlis CCD, CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

CCDC reference: 979593

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814000257/fk2077sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814000257/fk2077Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814000257/fk2077Isup3.mol

Supporting information file. DOI: 10.1107/S1600536814000257/fk2077Isup4.cml

checkCIF report


Comment top

In the past 10 years, interest in aziridinyl anions generated by direct deprotonation grew steadily (Florio & Luisi, 2010). In our group, deprotonation reactions in α- or β-position to amines are a frequent research topic (Gessner & Strohmann, 2007; Gessner & Strohmann, 2008a,b; Unkelbach et al., 2012). We synthesized the compound with the intention to study the deprotonation of the aziridine moiety, which features both the α- and β-position on the same carbon, as well as ringstrain specific effects. The knowledge of the exact structure of the deprotonation substrate is usefull for further discussions of metalleted or substituted derivatives. The succesful deprotonation of such aziridines similar to the title compound were already reported by Huang et al., 2009. The synthesis of the title compound via sulfonium ylide transfer was most recently reportet by Kavanagh et al., 2013.

π—π-Interactions between parallel phenyl groups of adjacent molecules are indicated by a plane-to-plane distance of 3.76 (1) Å, whereas the distance between the isopropyl substituted benzene rings is far longer with 6.30 (1) Å (distance of the centroids). Additionally, interactions between the phenyl ring and the perpendicular aziridine group of an adjacent molecule are possible, with a distance between the ipso-carbon (C9) and the aziridine carbon C1 of 3.43 (1) Å. Thus, a T-shaped π-interaction between the aromat and the aziridin moiety are supposable. The C—C-bonds in the triisopropyl substituted benzene ring are not equidistant, but show slight deviations, similar to those found in other structures containing that group (Sandrock et al., 2004, Laba et al., 2009). Longer C—C-bonds were observed at the ipso-carbon [C9—C10 1.416 (2) Å and C9—C14 1.415 (2) Å] than for the other [C10—C11 1.396 (2) Å, C11—C12 1.385 (2) Å and C12—C13 1.384 (2) Å]. In addition, C—O-distances [C16—O2 2.83 (1) Å and C22—O1 2.98 (1) Å] shorter than the sum of the corresponding van-der-waals radii suggest strong steric repulsion between the isopropyl groups and the sulfonyl oxygen atoms, causing the sulfur atom to bend out of the aromatic plane (defined by C9-C10-C11-C12-C13-C14) of which it deviates by 0.228 (2) Å.

Related literature top

For structures containing the triisopropylbenzenesulfonyl group with detailed discussion of the geometry, see: Sandrock et al. (2004); Laba et al. (2009). For the lithiation of activated aziridines, see: Huang et al. (2009) and for a general review on aziridinylanions, see: Florio & Luisi (2010). For the most recent synthesis of the title compound, see: Kavanagh et al. (2013). For deprotonation reactions of aziridinyl anions to amines, see: Gessner & Strohmann (2007, 2008a,b); Unkelbach et al. (2012).

Refinement top

All H atoms were placed in calculated positions (aromatic C-H = 0.95 Å, primary C-H = 0.98 Å, secondary C-H = 0.99 Å, tertiary C-H = 1.00 Å) and allowed to ride in the refinement with Uiso(H) = 1.2 Ueq(C) and Uiso(H) = 1.5 Ueq(C) for terminal groups.

Structure description top

In the past 10 years, interest in aziridinyl anions generated by direct deprotonation grew steadily (Florio & Luisi, 2010). In our group, deprotonation reactions in α- or β-position to amines are a frequent research topic (Gessner & Strohmann, 2007; Gessner & Strohmann, 2008a,b; Unkelbach et al., 2012). We synthesized the compound with the intention to study the deprotonation of the aziridine moiety, which features both the α- and β-position on the same carbon, as well as ringstrain specific effects. The knowledge of the exact structure of the deprotonation substrate is usefull for further discussions of metalleted or substituted derivatives. The succesful deprotonation of such aziridines similar to the title compound were already reported by Huang et al., 2009. The synthesis of the title compound via sulfonium ylide transfer was most recently reportet by Kavanagh et al., 2013.

π—π-Interactions between parallel phenyl groups of adjacent molecules are indicated by a plane-to-plane distance of 3.76 (1) Å, whereas the distance between the isopropyl substituted benzene rings is far longer with 6.30 (1) Å (distance of the centroids). Additionally, interactions between the phenyl ring and the perpendicular aziridine group of an adjacent molecule are possible, with a distance between the ipso-carbon (C9) and the aziridine carbon C1 of 3.43 (1) Å. Thus, a T-shaped π-interaction between the aromat and the aziridin moiety are supposable. The C—C-bonds in the triisopropyl substituted benzene ring are not equidistant, but show slight deviations, similar to those found in other structures containing that group (Sandrock et al., 2004, Laba et al., 2009). Longer C—C-bonds were observed at the ipso-carbon [C9—C10 1.416 (2) Å and C9—C14 1.415 (2) Å] than for the other [C10—C11 1.396 (2) Å, C11—C12 1.385 (2) Å and C12—C13 1.384 (2) Å]. In addition, C—O-distances [C16—O2 2.83 (1) Å and C22—O1 2.98 (1) Å] shorter than the sum of the corresponding van-der-waals radii suggest strong steric repulsion between the isopropyl groups and the sulfonyl oxygen atoms, causing the sulfur atom to bend out of the aromatic plane (defined by C9-C10-C11-C12-C13-C14) of which it deviates by 0.228 (2) Å.

For structures containing the triisopropylbenzenesulfonyl group with detailed discussion of the geometry, see: Sandrock et al. (2004); Laba et al. (2009). For the lithiation of activated aziridines, see: Huang et al. (2009) and for a general review on aziridinylanions, see: Florio & Luisi (2010). For the most recent synthesis of the title compound, see: Kavanagh et al. (2013). For deprotonation reactions of aziridinyl anions to amines, see: Gessner & Strohmann (2007, 2008a,b); Unkelbach et al. (2012).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2012); cell refinement: CrysAlis CCD (Oxford Diffraction, 2012); data reduction: CrysAlis RED (Oxford Diffraction, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound with displacement ellipsoids drawn at 50% probability level.
[Figure 2] Fig. 2. Molecular packing viewed along the a axis with H atoms omitted. Dashed lines indicate π-π-interactions.
rac-2-Phenyl-1-[(2,4,6-triisopropylbenzene)sulfonyl]aziridine top
Crystal data top
C23H31NO2SZ = 2
Mr = 385.55F(000) = 416
Triclinic, P1Dx = 1.166 Mg m−3
a = 6.3037 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.6995 (5) ÅCell parameters from 5958 reflections
c = 18.6675 (9) Åθ = 2.7–28.8°
α = 75.280 (4)°µ = 0.16 mm−1
β = 86.842 (4)°T = 173 K
γ = 84.404 (4)°Needle, colourless
V = 1098.11 (10) Å30.31 × 0.05 × 0.04 mm
Data collection top
Agilent Xcalibur Sapphire3
diffractometer		4314 independent reflections
Radiation source: Enhance (Mo) X-ray Source3633 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.045
Detector resolution: 16.0560 pixels mm-1θmax = 26.0°, θmin = 2.3°
φ and ω scansh = −7→7
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2012)		k = −11→11
Tmin = 0.952, Tmax = 1.000l = −22→22
17550 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0409P)2 + 0.5494P]
where P = (Fo2 + 2Fc2)/3
4314 reflections(Δ/σ)max = 0.001
250 parametersΔρmax = 0.34 e Å−3
0 restraintsΔρmin = −0.35 e Å−3
0 constraints
Crystal data top
C23H31NO2Sγ = 84.404 (4)°
Mr = 385.55V = 1098.11 (10) Å3
Triclinic, P1Z = 2
a = 6.3037 (3) ÅMo Kα radiation
b = 9.6995 (5) ŵ = 0.16 mm−1
c = 18.6675 (9) ÅT = 173 K
α = 75.280 (4)°0.31 × 0.05 × 0.04 mm
β = 86.842 (4)°
Data collection top
Agilent Xcalibur Sapphire3
diffractometer		4314 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2012)		3633 reflections with I > 2σ(I)
Tmin = 0.952, Tmax = 1.000Rint = 0.045
17550 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0420 restraints
wR(F2) = 0.107H-atom parameters constrained
S = 1.06Δρmax = 0.34 e Å−3
4314 reflectionsΔρmin = −0.35 e Å−3
250 parameters
Special details top

Experimental. Absorption correction: CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S0.05721 (6)0.42978 (4)0.83601 (2)0.02251 (13)
N0.2890 (2)0.41306 (14)0.87676 (7)0.0216 (3)
O10.01403 (19)0.28743 (12)0.83621 (7)0.0304 (3)
O2−0.10310 (19)0.51063 (13)0.87007 (7)0.0319 (3)
C10.3327 (3)0.52186 (18)0.91561 (10)0.0292 (4)
H1A0.22700.60570.91180.035*
H1B0.48290.54240.91720.035*
C20.2698 (3)0.38042 (18)0.95994 (9)0.0247 (4)
H20.12060.38050.98110.030*
C30.4221 (3)0.26355 (17)1.00030 (9)0.0228 (4)
C40.6286 (3)0.24228 (19)0.97333 (10)0.0298 (4)
H40.67410.30240.92770.036*
C50.7692 (3)0.1342 (2)1.01235 (11)0.0349 (4)
H50.91140.12200.99390.042*
C60.7035 (3)0.0440 (2)1.07802 (11)0.0382 (5)
H60.7998−0.03031.10470.046*
C70.4971 (4)0.0628 (2)1.10443 (11)0.0419 (5)
H70.45080.00021.14920.050*
C80.3560 (3)0.1726 (2)1.06619 (10)0.0322 (4)
H80.21440.18531.08510.039*
C90.1211 (3)0.52378 (17)0.74302 (9)0.0205 (3)
C100.0207 (3)0.66079 (17)0.71038 (9)0.0238 (4)
C110.0609 (3)0.71662 (18)0.63479 (9)0.0282 (4)
H11−0.00670.80770.61160.034*
C120.1947 (3)0.64572 (19)0.59189 (9)0.0286 (4)
C130.2961 (3)0.51463 (18)0.62672 (9)0.0272 (4)
H130.39140.46630.59810.033*
C140.2649 (3)0.45043 (17)0.70157 (9)0.0222 (4)
C15−0.0578 (5)0.9059 (2)0.73340 (15)0.0609 (7)
H15A−0.08360.95530.68150.091*
H15B0.09460.90110.74260.091*
H15C−0.13920.95850.76580.091*
C16−0.1279 (3)0.75541 (18)0.74931 (10)0.0309 (4)
H16−0.11700.71290.80380.037*
C17−0.3564 (4)0.7547 (3)0.73040 (19)0.0728 (9)
H17A−0.37320.79580.67710.109*
H17B−0.44840.81180.75810.109*
H17C−0.39680.65620.74360.109*
C180.3517 (5)0.8457 (3)0.49803 (14)0.0692 (8)
H18A0.26330.91770.51740.104*
H18B0.38150.88370.44500.104*
H18C0.48620.82190.52410.104*
C190.2340 (3)0.7118 (2)0.50981 (10)0.0397 (5)
H190.32780.64070.48940.048*
C200.0285 (4)0.7429 (3)0.46754 (13)0.0653 (7)
H20A−0.04430.65510.47620.098*
H20B0.06150.77770.41440.098*
H20C−0.06420.81600.48470.098*
C210.6302 (3)0.3192 (2)0.71540 (13)0.0451 (5)
H21A0.65870.33970.66180.068*
H21B0.71010.22920.73970.068*
H21C0.67460.39710.73420.068*
C220.3917 (3)0.30635 (18)0.73179 (10)0.0258 (4)
H220.36780.27820.78680.031*
C230.3133 (4)0.1912 (2)0.69989 (12)0.0403 (5)
H23A0.16110.18350.71230.060*
H23B0.39330.09920.72090.060*
H23C0.33520.21680.64590.060*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S0.0209 (2)0.0214 (2)0.0226 (2)−0.00145 (16)−0.00392 (16)−0.00021 (16)
N0.0227 (7)0.0221 (7)0.0195 (7)−0.0023 (6)−0.0030 (6)−0.0038 (5)
O10.0315 (7)0.0229 (6)0.0347 (7)−0.0073 (5)−0.0106 (5)0.0006 (5)
O20.0262 (7)0.0321 (7)0.0301 (7)0.0046 (5)0.0039 (5)0.0017 (5)
C10.0376 (10)0.0233 (9)0.0285 (9)−0.0014 (8)−0.0108 (8)−0.0080 (7)
C20.0295 (9)0.0259 (9)0.0188 (8)0.0015 (7)−0.0014 (7)−0.0071 (7)
C30.0278 (9)0.0220 (8)0.0205 (8)−0.0016 (7)−0.0050 (7)−0.0080 (7)
C40.0303 (10)0.0259 (9)0.0311 (10)−0.0029 (7)−0.0014 (8)−0.0027 (7)
C50.0295 (10)0.0320 (10)0.0425 (11)0.0035 (8)−0.0042 (8)−0.0094 (8)
C60.0482 (13)0.0290 (10)0.0352 (11)0.0106 (9)−0.0145 (9)−0.0066 (8)
C70.0572 (14)0.0366 (11)0.0245 (10)0.0046 (10)−0.0016 (9)0.0027 (8)
C80.0372 (11)0.0354 (10)0.0223 (9)0.0011 (8)0.0012 (8)−0.0059 (8)
C90.0227 (8)0.0200 (8)0.0189 (8)−0.0029 (6)−0.0058 (6)−0.0038 (6)
C100.0259 (9)0.0193 (8)0.0260 (9)0.0001 (7)−0.0035 (7)−0.0056 (7)
C110.0333 (10)0.0205 (8)0.0265 (9)0.0056 (7)−0.0045 (7)−0.0003 (7)
C120.0339 (10)0.0282 (9)0.0219 (9)0.0017 (8)−0.0053 (7)−0.0038 (7)
C130.0293 (9)0.0276 (9)0.0253 (9)0.0053 (7)−0.0040 (7)−0.0097 (7)
C140.0230 (9)0.0201 (8)0.0247 (8)−0.0001 (7)−0.0083 (7)−0.0065 (7)
C150.0812 (19)0.0319 (12)0.0736 (17)−0.0089 (12)0.0258 (14)−0.0251 (12)
C160.0393 (11)0.0205 (9)0.0295 (9)0.0048 (8)0.0035 (8)−0.0037 (7)
C170.0355 (13)0.084 (2)0.117 (3)0.0111 (13)−0.0003 (14)−0.0659 (19)
C180.087 (2)0.0712 (18)0.0413 (14)−0.0245 (15)0.0178 (13)0.0033 (12)
C190.0517 (13)0.0381 (11)0.0227 (9)0.0129 (9)0.0010 (9)−0.0022 (8)
C200.0744 (18)0.0837 (19)0.0292 (12)0.0079 (15)−0.0155 (12)−0.0012 (12)
C210.0329 (11)0.0404 (12)0.0580 (14)0.0097 (9)−0.0171 (10)−0.0066 (10)
C220.0306 (9)0.0219 (9)0.0253 (9)0.0054 (7)−0.0095 (7)−0.0073 (7)
C230.0517 (13)0.0244 (10)0.0470 (12)0.0056 (9)−0.0197 (10)−0.0126 (9)
Geometric parameters (Å, º) top
S—O11.4322 (12)C13—C141.389 (2)
S—O21.4382 (13)C13—H130.9500
S—N1.6597 (14)C14—C221.530 (2)
S—C91.7880 (16)C15—C161.518 (3)
N—C11.478 (2)C15—H15A0.9800
N—C21.504 (2)C15—H15B0.9800
C1—C21.489 (2)C15—H15C0.9800
C1—H1A0.9900C16—C171.503 (3)
C1—H1B0.9900C16—H161.0000
C2—C31.486 (2)C17—H17A0.9800
C2—H21.0000C17—H17B0.9800
C3—C41.385 (2)C17—H17C0.9800
C3—C81.389 (2)C18—C191.519 (3)
C4—C51.384 (3)C18—H18A0.9800
C4—H40.9500C18—H18B0.9800
C5—C61.382 (3)C18—H18C0.9800
C5—H50.9500C19—C201.519 (3)
C6—C71.378 (3)C19—H191.0000
C6—H60.9500C20—H20A0.9800
C7—C81.390 (3)C20—H20B0.9800
C7—H70.9500C20—H20C0.9800
C8—H80.9500C21—C221.528 (3)
C9—C141.415 (2)C21—H21A0.9800
C9—C101.416 (2)C21—H21B0.9800
C10—C111.396 (2)C21—H21C0.9800
C10—C161.531 (2)C22—C231.525 (2)
C11—C121.385 (2)C22—H221.0000
C11—H110.9500C23—H23A0.9800
C12—C131.384 (2)C23—H23B0.9800
C12—C191.520 (2)C23—H23C0.9800
O1—S—O2116.59 (8)C9—C14—C22125.91 (15)
O1—S—N105.66 (7)C16—C15—H15A109.5
O2—S—N111.07 (7)C16—C15—H15B109.5
O1—S—C9108.62 (7)H15A—C15—H15B109.5
O2—S—C9111.50 (7)C16—C15—H15C109.5
N—S—C9102.29 (7)H15A—C15—H15C109.5
C1—N—C259.91 (11)H15B—C15—H15C109.5
C1—N—S118.58 (11)C17—C16—C15112.2 (2)
C2—N—S113.79 (11)C17—C16—C10111.28 (16)
N—C1—C260.94 (10)C15—C16—C10111.45 (16)
N—C1—H1A117.7C17—C16—H16107.2
C2—C1—H1A117.7C15—C16—H16107.2
N—C1—H1B117.7C10—C16—H16107.2
C2—C1—H1B117.7C16—C17—H17A109.5
H1A—C1—H1B114.8C16—C17—H17B109.5
C3—C2—C1124.07 (16)H17A—C17—H17B109.5
C3—C2—N115.58 (13)C16—C17—H17C109.5
C1—C2—N59.15 (10)H17A—C17—H17C109.5
C3—C2—H2115.3H17B—C17—H17C109.5
C1—C2—H2115.3C19—C18—H18A109.5
N—C2—H2115.3C19—C18—H18B109.5
C4—C3—C8119.08 (16)H18A—C18—H18B109.5
C4—C3—C2121.46 (15)C19—C18—H18C109.5
C8—C3—C2119.45 (16)H18A—C18—H18C109.5
C5—C4—C3120.59 (17)H18B—C18—H18C109.5
C5—C4—H4119.7C20—C19—C18111.1 (2)
C3—C4—H4119.7C20—C19—C12111.87 (18)
C6—C5—C4120.28 (18)C18—C19—C12110.91 (17)
C6—C5—H5119.9C20—C19—H19107.6
C4—C5—H5119.9C18—C19—H19107.6
C7—C6—C5119.43 (18)C12—C19—H19107.6
C7—C6—H6120.3C19—C20—H20A109.5
C5—C6—H6120.3C19—C20—H20B109.5
C6—C7—C8120.63 (18)H20A—C20—H20B109.5
C6—C7—H7119.7C19—C20—H20C109.5
C8—C7—H7119.7H20A—C20—H20C109.5
C3—C8—C7119.96 (18)H20B—C20—H20C109.5
C3—C8—H8120.0C22—C21—H21A109.5
C7—C8—H8120.0C22—C21—H21B109.5
C14—C9—C10121.29 (15)H21A—C21—H21B109.5
C14—C9—S116.84 (12)C22—C21—H21C109.5
C10—C9—S121.69 (12)H21A—C21—H21C109.5
C11—C10—C9117.04 (15)H21B—C21—H21C109.5
C11—C10—C16116.07 (14)C23—C22—C21111.22 (16)
C9—C10—C16126.88 (15)C23—C22—C14110.57 (14)
C12—C11—C10123.22 (15)C21—C22—C14110.51 (15)
C12—C11—H11118.4C23—C22—H22108.1
C10—C11—H11118.4C21—C22—H22108.1
C13—C12—C11117.74 (16)C14—C22—H22108.1
C13—C12—C19121.16 (16)C22—C23—H23A109.5
C11—C12—C19121.07 (16)C22—C23—H23B109.5
C12—C13—C14123.04 (16)H23A—C23—H23B109.5
C12—C13—H13118.5C22—C23—H23C109.5
C14—C13—H13118.5H23A—C23—H23C109.5
C13—C14—C9117.56 (15)H23B—C23—H23C109.5
C13—C14—C22116.53 (15)

Experimental details

Crystal data
Chemical formulaC23H31NO2S
Mr385.55
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)6.3037 (3), 9.6995 (5), 18.6675 (9)
α, β, γ (°)75.280 (4), 86.842 (4), 84.404 (4)
V (Å3)1098.11 (10)
Z2
Radiation typeMo Kα
µ (mm−1)0.16
Crystal size (mm)0.31 × 0.05 × 0.04
Data collection
DiffractometerAgilent Xcalibur Sapphire3
Absorption correctionMulti-scan
(CrysAlis PRO; Oxford Diffraction, 2012)
Tmin, Tmax0.952, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections		17550, 4314, 3633
Rint0.045
(sin θ/λ)max (Å−1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.107, 1.06
No. of reflections4314
No. of parameters250
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.34, −0.35

Computer programs: CrysAlis CCD (Oxford Diffraction, 2012), CrysAlis RED (Oxford Diffraction, 2012), SHELXS97 (Sheldrick, 2008), SHELXL2013 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), publCIF (Westrip, 2010).

Deviation of atoms from the benzene ring least-squares plane (Å). top
AtomDeviation
C90.020 (1)
C10-0.013 (1)
C11-0.005 (1)
C120.015 (1)
C13-0.009 (1)
C14-0.009 (1)
S1*0.228 (2)
Note: (*) not used in the least-squares-plane calculation.
 

Acknowledgements

We thank the Deutsche Forschungsgemeinschaft (DFG) for financial support.

References

First citationFlorio, S. & Luisi, R. (2010). Chem. Rec. 110, 5128–5157.  Web of Science CrossRef CAS Google Scholar
 First citationGessner, V. H. & Strohmann, C. (2007). Angew. Chem. Int. Ed. 46, 4566–4569.  Google Scholar
 First citationGessner, V. H. & Strohmann, C. (2008a). Angew. Chem. Int. Ed. 46, 8281–8283.  Google Scholar
 First citationGessner, V. H. & Strohmann, C. (2008b). J. Am. Chem. Soc. 130, 14412–14413.  Web of Science CSD CrossRef PubMed CAS Google Scholar
 First citationHuang, J., Moore, S. P., O'Brien, P., Whitwood, A. C. & Gilday, J. (2009). Org. Biomol. Chem. 7, 335–345.  Web of Science CSD CrossRef PubMed Google Scholar
 First citationKavanagh, S. A., Piccini, A. & Connon, S. J. (2013). Org. Biomol. Chem. 11, 3535–3540.  Web of Science CrossRef CAS PubMed Google Scholar
 First citationLaba, V. I., Sviridova, A. V. & Nesterov, V. N. (2009). Kristallografiya, 54, 44–47.  CAS Google Scholar
 First citationOxford Diffraction (2012). CrysAlis CCD, CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.  Google Scholar
 First citationSandrock, P. B., Meyers, C. Y., Rath, N. P. & Robinson, P. D. (2004). Acta Cryst. E60, o544–o546.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationUnkelbach, C., Rosenbaum, H. S. & Strohmann, C. (2012). Chem. Commun. 48, 10612–10614.  Web of Science CSD CrossRef CAS Google Scholar
 First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationZhu, J., Zhang, M.-J., Liu, Q.-W. & Pan, Z.-H. (2006). Acta Cryst. E62, o1507–o1508.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 70| Part 2| February 2014| Page o153
doi:10.1107/S1600536814000257
Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS