Crystal structure of 1-[(2,4,6-triiso­propyl­phen­yl)sulfon­yl]aziridine

Knauer, L.; Golz, C.; Strohmann, C.

doi:10.1107/S2056989015010221

organic compounds

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ISSN: 2056-9890

Volume 71| Part 7| July 2015| Pages o438-o439

doi:10.1107/S2056989015010221

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Crystal structure of 1-[(2,4,6-triisopropylphenyl)sulfonyl]aziridine

Lena Knauer,^a Christopher Golz ^a and Carsten Strohmann ^a ^*

^aFakultät für Chemie und Chemische Biologie, Technische Universität Dortmund, Otto-Hahn-Strasse 6, 44227 Dortmund, Germany
^*Correspondence e-mail: carsten.strohmann@tu-dortmund.de

Edited by U. Flörke, University of Paderborn, Germany (Received 30 April 2015; accepted 27 May 2015; online 3 June 2015)

The title compound, C₁₇H₂₇NO₂S, exhibits a distorted geometry of the aromatic ring with elongated bonds at the ipso-C atom. The S atom deviates from the aromatic ring plane by 0.393 (4) Å. Similar to this, the adjacent isopropyl groups are bent out of the aromatic ring plane by −0.125 (4) and −0.154 (4) Å. Even the distant isopropyl group in para-position to the sulfonyl moiety shows a slight deviation from the ring plane of 0.111 (5) Å. These distortions, which are caused by the bulky substituents, can also be observed in related sulfonylaziridine structures.

Keywords: crystal structure; aziridine; triisopropylbenzenesulfonyl; consecutive ring-opening reactions.

CCDC reference: 1403377

1. Related literature

For the crystal structure of a related phenyl-substituted compound, see: Golz et al. (2014 ). For a discussion of the geometry of the triisopropylbenzenesulfonyl moiety, see: Sandrock et al. (2004 ). For a discussion of the pyramidalized geometry of N-sulfonylamides, see: Ohwada et al. (1998 ). By regioselective ring opening reactions, countless nitrogen-containing compounds are accessible, see: Stamm (1999 ); Schneider (2009 ). For consecutive ring-opening reactions of aziridines by triethylamine, see: Golz & Strohmann (2015 ). In some cases, the three-membered aziridine ring is further activated by electron-withdrawing groups (Hu, 2004 ) to increase its reactivity.

2. Experimental

2.1. Crystal data

C₁₇H₂₇NO₂S
M_r = 309.45
Monoclinic, P 2₁ /c
a = 6.2679 (8) Å
b = 17.5289 (18) Å
c = 16.3890 (13) Å
β = 100.331 (10)°
V = 1771.5 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 173 K
0.33 × 0.25 × 0.01 mm

2.2. Data collection

Agilent Xcalibur Sapphire3 diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013 $[Agilent (2013). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ) T_min = 0.782, T_max = 1.000
9521 measured reflections
3449 independent reflections
2479 reflections with I > 2σ(I)
R_int = 0.049

2.3. Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.141
S = 1.07
3449 reflections
196 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.58 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2013 $[Agilent (2013). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ); molecular graphics: OLEX2 (Dolomanov et al., 2009 ); software used to prepare material for publication: OLEX2.

Supporting information

CCDC reference: 1403377

Crystal structure: contains datablock I. DOI: 10.1107/S2056989015010221/fk2088sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015010221/fk2088Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989015010221/fk2088Isup3.cml

checkCIF report

Structural commentary top

Aziridines are interesting and versatile building blocks in synthetic chemistry due to their high ring strain. By regioselective ring opening reactions, countless nitrogen-containing compounds are accessible (Stamm, 1999; Schneider, 2009). For example, the aziridine ring can be opened by triethylamine (Golz & Strohmann, 2015). In some cases, the three-membered aziridine ring is further activated by electron-withdrawing groups (Hu, 2004) to increase its reactivity.

The title compound, C₁₇H₂₇NO₂S, is a representative of the class of activated aziridines, as it contains a triisopropylbenzene substituted sulfonyl ester attached to the nitrogen atom. In the aromatic ring, the bulky substituents lead to a distortion of its geometry. This is expressed by the increased bond lengths and out-of-plane bent substituents around the benzene ring. At the ipso-carbon, the bonds C10–C11 and C10–C6 are slightly elongated to 1.410 (3) Å. In contrast, the other bonds of the aromatic ring exhibit usual lengths [C4–C15 1.374 (3) Å, C5–C61.380 (3) Å, C11–C15 1.388 (3) Å, C4–C5 1.389 (3) Å]. The sulfonyl group as well as the adjacent isopropyl groups bend out of the aromatic plane. This is caused by steric repulsion between the isopropyl groups and the sulfonyl oxygen atoms. The sulfur atom deviates from the mean aromatic ring plane by 0.393 (4) Å. The carbon atoms C7 and C12 show distances of -0.125 (4) Å and -0.154 (4) Å, respectively (see Table 5). A similar distortion can also be observed at the isopropyl group in para position to the sulfonyl moiety. Here, C1 has a distance to the aromatic ring plane of 0.111 (5) Å, thus being distorted in the same direction as the sulfur atom. This is caused by steric repulsion between the C1 isopropyl group and the adjacent isopropyl groups in ortho position in respect of the sulfonyl moiety.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1.

Hydrogen atoms were located from difference Fourier maps, refined at idealized positions riding on the carbon atoms with isotropic displacement parameters U_iso(H) = 1.2U_eq(C) or 1.5U_eq(–CH₃) and aromatic C–H = 0.95 Å, primary C–H = 0.98 Å, secondary C–H = 0.99 Å, tertiary C–H = 1.00 Å. All CH₃ hydrogen atoms were allowed to rotate but not to tip. Aziridine protons could be located from difference Fourier maps, but were refined as idealized CH₂ groups.

Related literature top

For the crystal structure of a related phenyl-substituted compound, see: Golz et al. (2014). For a discussion of the geometry of the triisopropylbenzenesulfonyl moiety, see: Sandrock et al. (2004). For a discussion of the pyramidalized geometry of N-sulfonylamides, see: Ohwada et al. (1998). By regioselective ring opening reactions, countless nitrogen-containing compounds are accessible, see: Stamm (1999); Schneider (2009). For consecutive ring-opening reactions of aziridines by triethylamine, see: Golz & Strohmann (2015). In some cases, the three-membered aziridine ring is further activated by electron-withdrawing groups (Hu, 2004) to increase its reactivity.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top

Fig. 1. Molecular structure of the title compound with anisotropic displacement ellipsoids drawn at 50% probability level.

(I) top

Crystal data top

C₁₇H₂₇NO₂S	F(000) = 672
M_r = 309.45	D_x = 1.160 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 6.2679 (8) Å	Cell parameters from 2277 reflections
b = 17.5289 (18) Å	θ = 3.3–29.2°
c = 16.3890 (13) Å	µ = 0.19 mm⁻¹
β = 100.331 (10)°	T = 173 K
V = 1771.5 (3) Å³	Plate, colourless
Z = 4	0.33 × 0.25 × 0.01 mm

Data collection top

Agilent Xcalibur Sapphire3 diffractometer	3449 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2479 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
Detector resolution: 16.0560 pixels mm^-1	θ_max = 26.0°, θ_min = 2.5°
ω scans	h = −7→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	k = −15→21
T_min = 0.782, T_max = 1.000	l = −20→20
9521 measured reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.053	H-atom parameters constrained
wR(F²) = 0.141	w = 1/[σ²(F_o²) + (0.0473P)² + 0.8936P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
3449 reflections	Δρ_max = 0.33 e Å⁻³
196 parameters	Δρ_min = −0.58 e Å⁻³

Crystal data top

C₁₇H₂₇NO₂S	V = 1771.5 (3) Å³
M_r = 309.45	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.2679 (8) Å	µ = 0.19 mm⁻¹
b = 17.5289 (18) Å	T = 173 K
c = 16.3890 (13) Å	0.33 × 0.25 × 0.01 mm
β = 100.331 (10)°

Data collection top

Agilent Xcalibur Sapphire3 diffractometer	3449 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	2479 reflections with I > 2σ(I)
T_min = 0.782, T_max = 1.000	R_int = 0.049
9521 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.141	H-atom parameters constrained
S = 1.07	Δρ_max = 0.33 e Å⁻³
3449 reflections	Δρ_min = −0.58 e Å⁻³
196 parameters

Special details top

Experimental. Absorption correction: CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) 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

	x	y	z	U_iso*/U_eq
S1	0.71473 (10)	0.20619 (4)	0.37952 (4)	0.0245 (2)
C10	0.7527 (4)	0.26810 (13)	0.29748 (14)	0.0205 (5)
C15	0.8227 (4)	0.28863 (14)	0.16069 (15)	0.0272 (6)
H15	0.8229	0.2705	0.1061	0.033*
C6	0.8105 (4)	0.34434 (14)	0.31802 (14)	0.0246 (6)
C5	0.8842 (4)	0.38836 (15)	0.25903 (15)	0.0297 (6)
H5	0.9273	0.4394	0.2726	0.036*
C11	0.7462 (4)	0.24050 (14)	0.21624 (15)	0.0243 (6)
C4	0.8981 (4)	0.36110 (15)	0.18058 (15)	0.0279 (6)
O1	0.7219 (3)	0.12858 (10)	0.35547 (11)	0.0370 (5)
O2	0.8625 (3)	0.22687 (11)	0.45315 (10)	0.0360 (5)
N1	0.4729 (4)	0.23217 (13)	0.39562 (14)	0.0345 (6)
C17	0.3491 (5)	0.17365 (19)	0.4317 (2)	0.0500 (9)
H17A	0.4185	0.1234	0.4451	0.060*
H17B	0.2536	0.1908	0.4702	0.060*
C16	0.2886 (6)	0.1945 (3)	0.3447 (2)	0.0701 (12)
H16A	0.1543	0.2246	0.3280	0.084*
H16B	0.3190	0.1572	0.3029	0.084*
C12	0.6577 (5)	0.16388 (14)	0.18281 (15)	0.0312 (6)
H12	0.5872	0.1391	0.2261	0.037*
C7	0.7975 (4)	0.38301 (14)	0.40041 (15)	0.0290 (6)
H7	0.7291	0.3463	0.4347	0.035*
C1	0.9900 (5)	0.41027 (15)	0.11913 (15)	0.0331 (7)
H1	0.9766	0.3811	0.0660	0.040*
C13	0.4860 (6)	0.17400 (18)	0.10515 (18)	0.0489 (9)
H13A	0.3751	0.2099	0.1166	0.073*
H13B	0.4184	0.1246	0.0887	0.073*
H13C	0.5539	0.1940	0.0602	0.073*
C3	0.8614 (5)	0.48402 (17)	0.10107 (18)	0.0457 (8)
H3A	0.7095	0.4719	0.0787	0.068*
H3B	0.9223	0.5142	0.0605	0.068*
H3C	0.8695	0.5133	0.1525	0.068*
C14	0.8399 (5)	0.11176 (17)	0.1661 (2)	0.0471 (8)
H14A	0.9167	0.1361	0.1259	0.071*
H14B	0.7787	0.0631	0.1436	0.071*
H14C	0.9415	0.1026	0.2180	0.071*
C2	1.2285 (5)	0.42692 (19)	0.1493 (2)	0.0496 (9)
H2A	1.2459	0.4567	0.2006	0.074*
H2B	1.2856	0.4560	0.1068	0.074*
H2C	1.3083	0.3788	0.1597	0.074*
C8	1.0244 (5)	0.40142 (17)	0.44750 (16)	0.0407 (8)
H8A	1.1099	0.3544	0.4564	0.061*
H8B	1.0137	0.4243	0.5012	0.061*
H8C	1.0951	0.4374	0.4151	0.061*
C9	0.6542 (6)	0.45350 (17)	0.38647 (18)	0.0476 (8)
H9A	0.7228	0.4919	0.3562	0.071*
H9B	0.6351	0.4744	0.4401	0.071*
H9C	0.5125	0.4396	0.3541	0.071*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0289 (4)	0.0256 (4)	0.0205 (3)	0.0015 (3)	0.0085 (3)	0.0032 (3)
C10	0.0213 (13)	0.0238 (13)	0.0168 (11)	0.0008 (10)	0.0048 (10)	0.0025 (10)
C15	0.0372 (16)	0.0275 (14)	0.0178 (12)	−0.0032 (12)	0.0077 (11)	−0.0036 (10)
C6	0.0284 (14)	0.0279 (14)	0.0174 (12)	−0.0012 (11)	0.0039 (11)	−0.0011 (10)
C5	0.0401 (17)	0.0269 (14)	0.0228 (13)	−0.0082 (12)	0.0077 (12)	−0.0035 (11)
C11	0.0283 (14)	0.0233 (13)	0.0212 (12)	0.0003 (11)	0.0043 (11)	−0.0005 (10)
C4	0.0358 (16)	0.0297 (15)	0.0190 (12)	−0.0034 (12)	0.0068 (11)	0.0003 (11)
O1	0.0590 (14)	0.0250 (10)	0.0292 (10)	0.0063 (9)	0.0137 (10)	0.0051 (8)
O2	0.0431 (13)	0.0460 (12)	0.0184 (9)	−0.0037 (9)	0.0036 (9)	0.0068 (8)
N1	0.0286 (13)	0.0448 (14)	0.0326 (12)	−0.0001 (11)	0.0128 (11)	0.0007 (11)
C17	0.0423 (19)	0.053 (2)	0.063 (2)	−0.0197 (15)	0.0294 (17)	−0.0063 (17)
C16	0.0294 (19)	0.123 (4)	0.059 (2)	−0.014 (2)	0.0122 (17)	−0.030 (2)
C12	0.0473 (18)	0.0251 (14)	0.0221 (13)	−0.0042 (12)	0.0088 (12)	−0.0015 (11)
C7	0.0442 (17)	0.0251 (14)	0.0197 (12)	−0.0084 (12)	0.0115 (12)	−0.0048 (11)
C1	0.0504 (18)	0.0296 (15)	0.0224 (13)	−0.0063 (13)	0.0152 (13)	−0.0008 (11)
C13	0.060 (2)	0.0442 (19)	0.0360 (16)	−0.0173 (16)	−0.0084 (16)	−0.0013 (14)
C3	0.060 (2)	0.0423 (19)	0.0371 (16)	−0.0001 (16)	0.0160 (16)	0.0155 (14)
C14	0.059 (2)	0.0336 (17)	0.0517 (19)	−0.0011 (15)	0.0181 (17)	−0.0145 (15)
C2	0.047 (2)	0.055 (2)	0.0497 (19)	−0.0071 (16)	0.0182 (16)	0.0124 (16)
C8	0.056 (2)	0.0432 (18)	0.0215 (13)	−0.0145 (15)	0.0028 (14)	−0.0060 (13)
C9	0.070 (2)	0.0402 (18)	0.0353 (16)	0.0090 (16)	0.0172 (16)	−0.0109 (14)

Geometric parameters (Å, º) top

S1—C10	1.777 (2)	C7—H7	1.0000
S1—O1	1.4193 (19)	C7—C8	1.526 (4)
S1—O2	1.4300 (19)	C7—C9	1.520 (4)
S1—N1	1.649 (2)	C1—H1	1.0000
C10—C6	1.410 (3)	C1—C3	1.524 (4)
C10—C11	1.410 (3)	C1—C2	1.517 (4)
C15—H15	0.9500	C13—H13A	0.9800
C15—C11	1.388 (3)	C13—H13B	0.9800
C15—C4	1.374 (4)	C13—H13C	0.9800
C6—C5	1.380 (3)	C3—H3A	0.9800
C6—C7	1.526 (3)	C3—H3B	0.9800
C5—H5	0.9500	C3—H3C	0.9800
C5—C4	1.389 (3)	C14—H14A	0.9800
C11—C12	1.518 (4)	C14—H14B	0.9800
C4—C1	1.516 (3)	C14—H14C	0.9800
N1—C17	1.473 (3)	C2—H2A	0.9800
N1—C16	1.456 (4)	C2—H2B	0.9800
C17—H17A	0.9900	C2—H2C	0.9800
C17—H17B	0.9900	C8—H8A	0.9800
C17—C16	1.455 (5)	C8—H8B	0.9800
C16—H16A	0.9900	C8—H8C	0.9800
C16—H16B	0.9900	C9—H9A	0.9800
C12—H12	1.0000	C9—H9B	0.9800
C12—C13	1.523 (4)	C9—H9C	0.9800
C12—C14	1.526 (4)

O1—S1—C10	111.10 (11)	C8—C7—H7	107.9
O1—S1—O2	115.43 (12)	C9—C7—C6	110.6 (2)
O1—S1—N1	112.65 (12)	C9—C7—H7	107.9
O2—S1—C10	109.23 (11)	C9—C7—C8	112.1 (2)
O2—S1—N1	105.67 (12)	C4—C1—H1	107.8
N1—S1—C10	101.77 (11)	C4—C1—C3	111.1 (2)
C6—C10—S1	117.51 (17)	C4—C1—C2	111.3 (2)
C6—C10—C11	120.9 (2)	C3—C1—H1	107.8
C11—C10—S1	121.32 (19)	C2—C1—H1	107.8
C11—C15—H15	118.3	C2—C1—C3	110.9 (2)
C4—C15—H15	118.3	C12—C13—H13A	109.5
C4—C15—C11	123.4 (2)	C12—C13—H13B	109.5
C10—C6—C7	125.5 (2)	C12—C13—H13C	109.5
C5—C6—C10	117.8 (2)	H13A—C13—H13B	109.5
C5—C6—C7	116.7 (2)	H13A—C13—H13C	109.5
C6—C5—H5	118.6	H13B—C13—H13C	109.5
C6—C5—C4	122.7 (2)	C1—C3—H3A	109.5
C4—C5—H5	118.6	C1—C3—H3B	109.5
C10—C11—C12	126.2 (2)	C1—C3—H3C	109.5
C15—C11—C10	117.1 (2)	H3A—C3—H3B	109.5
C15—C11—C12	116.6 (2)	H3A—C3—H3C	109.5
C15—C4—C5	117.5 (2)	H3B—C3—H3C	109.5
C15—C4—C1	121.6 (2)	C12—C14—H14A	109.5
C5—C4—C1	120.9 (2)	C12—C14—H14B	109.5
C17—N1—S1	116.0 (2)	C12—C14—H14C	109.5
C16—N1—S1	116.1 (2)	H14A—C14—H14B	109.5
C16—N1—C17	59.5 (2)	H14A—C14—H14C	109.5
N1—C17—H17A	117.8	H14B—C14—H14C	109.5
N1—C17—H17B	117.8	C1—C2—H2A	109.5
H17A—C17—H17B	114.9	C1—C2—H2B	109.5
C16—C17—N1	59.7 (2)	C1—C2—H2C	109.5
C16—C17—H17A	117.8	H2A—C2—H2B	109.5
C16—C17—H17B	117.8	H2A—C2—H2C	109.5
N1—C16—H16A	117.7	H2B—C2—H2C	109.5
N1—C16—H16B	117.7	C7—C8—H8A	109.5
C17—C16—N1	60.8 (2)	C7—C8—H8B	109.5
C17—C16—H16A	117.7	C7—C8—H8C	109.5
C17—C16—H16B	117.7	H8A—C8—H8B	109.5
H16A—C16—H16B	114.8	H8A—C8—H8C	109.5
C11—C12—H12	107.9	H8B—C8—H8C	109.5
C11—C12—C13	110.9 (2)	C7—C9—H9A	109.5
C11—C12—C14	111.0 (2)	C7—C9—H9B	109.5
C13—C12—H12	107.9	C7—C9—H9C	109.5
C13—C12—C14	111.1 (2)	H9A—C9—H9B	109.5
C14—C12—H12	107.9	H9A—C9—H9C	109.5
C6—C7—H7	107.9	H9B—C9—H9C	109.5
C8—C7—C6	110.4 (2)

S1—C10—C6—C5	166.7 (2)	C5—C6—C7—C8	−67.6 (3)
S1—C10—C6—C7	−13.6 (3)	C5—C6—C7—C9	57.1 (3)
S1—C10—C11—C15	−166.5 (2)	C5—C4—C1—C3	−58.7 (4)
S1—C10—C11—C12	15.3 (4)	C5—C4—C1—C2	65.4 (3)
S1—N1—C17—C16	−106.4 (3)	C11—C10—C6—C5	−7.3 (4)
S1—N1—C16—C17	106.1 (2)	C11—C10—C6—C7	172.4 (3)
C10—S1—N1—C17	154.1 (2)	C11—C15—C4—C5	−3.9 (4)
C10—S1—N1—C16	87.0 (2)	C11—C15—C4—C1	177.0 (3)
C10—C6—C5—C4	1.6 (4)	C4—C15—C11—C10	−1.5 (4)
C10—C6—C7—C8	112.8 (3)	C4—C15—C11—C12	176.8 (2)
C10—C6—C7—C9	−122.6 (3)	O1—S1—C10—C6	−162.51 (19)
C10—C11—C12—C13	125.2 (3)	O1—S1—C10—C11	11.4 (3)
C10—C11—C12—C14	−110.8 (3)	O1—S1—N1—C17	35.1 (2)
C15—C11—C12—C13	−52.9 (3)	O1—S1—N1—C16	−32.0 (3)
C15—C11—C12—C14	71.0 (3)	O2—S1—C10—C6	−34.0 (2)
C15—C4—C1—C3	120.4 (3)	O2—S1—C10—C11	139.9 (2)
C15—C4—C1—C2	−115.5 (3)	O2—S1—N1—C17	−91.8 (2)
C6—C10—C11—C15	7.2 (4)	O2—S1—N1—C16	−158.9 (2)
C6—C10—C11—C12	−170.9 (2)	N1—S1—C10—C6	77.4 (2)
C6—C5—C4—C15	3.8 (4)	N1—S1—C10—C11	−108.7 (2)
C6—C5—C4—C1	−177.1 (3)	C7—C6—C5—C4	−178.1 (3)

Experimental details

Crystal data
Chemical formula	C₁₇H₂₇NO₂S
M_r	309.45
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	6.2679 (8), 17.5289 (18), 16.3890 (13)
β (°)	100.331 (10)
V (Å³)	1771.5 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.33 × 0.25 × 0.01

Data collection
Diffractometer	Agilent Xcalibur Sapphire3 diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2013)
T_min, T_max	0.782, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	9521, 3449, 2479
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.141, 1.07
No. of reflections	3449
No. of parameters	196
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.58

Computer programs: CrysAlis PRO (Agilent, 2013), SHELXS97 (Sheldrick, 2008), SHELXL2014 (Sheldrick, 2015), OLEX2 (Dolomanov et al., 2009).

Deviation of atoms from the benzene ring least-square plane (Å). top

Atom	Deviation
C4	0.033 (2)
C5	-0.013 (2)
C6	-0.026 (2)
C10	0.046 (2)
C11	-0.026 (2)
C15	-0.014 (2)
S1*	0.393 (4)
C1*	0.111 (5)
C7*	-0.125 (4)
C12*	-0.154 (4)

Note: (*) not used in the least-squares-plane calculation.

Acknowledgements

We are grateful to the Deutsche Forschungsgemeinschaft (DFG) for financial support.

References

Agilent (2013). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England. Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Golz, C., Preut, H. & Strohmann, C. (2014). Acta Cryst. E70, o153. CSD CrossRef IUCr Journals Google Scholar
Golz, C. & Strohmann, C. (2015). Acta Cryst. E71, 564–566. CSD CrossRef IUCr Journals Google Scholar
Hu, X. E. (2004). Tetrahedron, 60, 2701–2743. Web of Science CrossRef CAS Google Scholar
Ohwada, T., Okamoto, I., Shudo, K. & Yamaguchi, K. (1998). Tetrahedron Lett. 39, 7877–7880. Web of Science CSD CrossRef CAS Google Scholar
Sandrock, 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
Schneider, C. (2009). Angew. Chem. Int. Ed. 48, 2082–2084. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Stamm, H. (1999). J. Prakt. Chem. 341, 319–331. CrossRef CAS Google Scholar

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Volume 71| Part 7| July 2015| Pages o438-o439

doi:10.1107/S2056989015010221

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