Crystal structure of 1-[(2,4,6-triiso-propyl-phen-yl)sulfon-yl]aziridine.

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 sulfonyl-aziridine structures.

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.

Experimental

Crystal data

C17H27NO2S

M = 309.45

Monoclinic,

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

Data collection

Agilent Xcalibur Sapphire3 diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013 ▸) T min = 0.782, T max = 1.000

9521 measured reflections

3449 independent reflections

2479 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.141

S = 1.07

3449 reflections

196 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.58 e Å−3

Data collection: CrysAlis PRO (Agilent, 2013 ▸); 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.

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

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

Click here for additional data file.

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

Click here for additional data file.

. DOI: 10.1107/S2056989015010221/fk2088fig1.tif

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

CCDC reference: 1403377

Additional supporting information: crystallographic information; 3D view; checkCIF report

C17H27NO2S	F(000) = 672
Mr = 309.45	Dx = 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

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

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(Fo2) + (0.0473P)2 + 0.8936P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
3449 reflections	Δρmax = 0.33 e Å−3
196 parameters	Δρmin = −0.58 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)