rac-2-Phenyl-1-[(2,4,6-triiso-propyl-benzene)-sulfon-yl]aziridine.

In the title compound, C23H31NO2S, the geometry of the triiso-propyl-phenyl 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-toluene-sulfonyl-aziridine [Zhu et al. (2006 ▶). Acta Cryst. E62, o1507-o1508]. π-π inter-actions between adjacent benzene rings [centroid-centroid distance = 3.7928 (11) Å] and are observed.

Related literature

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 ▶).

Experimental

Crystal data

C23H31NO2S

M = 385.55

Triclinic,

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 ▶) T min = 0.952, T max = 1.000

17550 measured reflections

4314 independent reflections

3633 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 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 ▶); cell refinement: CrysAlis CCD; 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 ▶).

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

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

Click here for additional data file.

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

Click here for additional data file.

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

CCDC reference:

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

C23H31NO2S	Z = 2
Mr = 385.55	F(000) = 416
Triclinic, P1	Dx = 1.166 Mg m−3
a = 6.3037 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.6995 (5) Å	Cell parameters from 5958 reflections
c = 18.6675 (9) Å	θ = 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) Å3	0.31 × 0.05 × 0.04 mm

Agilent Xcalibur Sapphire3 diffractometer	4314 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3633 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
Detector resolution: 16.0560 pixels mm-1	θmax = 26.0°, θmin = 2.3°
φ and ω scans	h = −7→7
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2012)	k = −11→11
Tmin = 0.952, Tmax = 1.000	l = −22→22
17550 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H-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 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.35 e Å−3
0 constraints

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.

	x	y	z	Uiso*/Ueq
S	0.05721 (6)	0.42978 (4)	0.83601 (2)	0.02251 (13)
N	0.2890 (2)	0.41306 (14)	0.87676 (7)	0.0216 (3)
O1	0.01403 (19)	0.28743 (12)	0.83621 (7)	0.0304 (3)
O2	−0.10310 (19)	0.51063 (13)	0.87007 (7)	0.0319 (3)
C1	0.3327 (3)	0.52186 (18)	0.91561 (10)	0.0292 (4)
H1A	0.2270	0.6057	0.9118	0.035*
H1B	0.4829	0.5424	0.9172	0.035*
C2	0.2698 (3)	0.38042 (18)	0.95994 (9)	0.0247 (4)
H2	0.1206	0.3805	0.9811	0.030*
C3	0.4221 (3)	0.26355 (17)	1.00030 (9)	0.0228 (4)
C4	0.6286 (3)	0.24228 (19)	0.97333 (10)	0.0298 (4)
H4	0.6741	0.3024	0.9277	0.036*
C5	0.7692 (3)	0.1342 (2)	1.01235 (11)	0.0349 (4)
H5	0.9114	0.1220	0.9939	0.042*
C6	0.7035 (3)	0.0440 (2)	1.07802 (11)	0.0382 (5)
H6	0.7998	−0.0303	1.1047	0.046*
C7	0.4971 (4)	0.0628 (2)	1.10443 (11)	0.0419 (5)
H7	0.4508	0.0002	1.1492	0.050*
C8	0.3560 (3)	0.1726 (2)	1.06619 (10)	0.0322 (4)
H8	0.2144	0.1853	1.0851	0.039*
C9	0.1211 (3)	0.52378 (17)	0.74302 (9)	0.0205 (3)
C10	0.0207 (3)	0.66079 (17)	0.71038 (9)	0.0238 (4)
C11	0.0609 (3)	0.71662 (18)	0.63479 (9)	0.0282 (4)
H11	−0.0067	0.8077	0.6116	0.034*
C12	0.1947 (3)	0.64572 (19)	0.59189 (9)	0.0286 (4)
C13	0.2961 (3)	0.51463 (18)	0.62672 (9)	0.0272 (4)
H13	0.3914	0.4663	0.5981	0.033*
C14	0.2649 (3)	0.45043 (17)	0.70157 (9)	0.0222 (4)
C15	−0.0578 (5)	0.9059 (2)	0.73340 (15)	0.0609 (7)
H15A	−0.0836	0.9553	0.6815	0.091*
H15B	0.0946	0.9011	0.7426	0.091*
H15C	−0.1392	0.9585	0.7658	0.091*
C16	−0.1279 (3)	0.75541 (18)	0.74931 (10)	0.0309 (4)
H16	−0.1170	0.7129	0.8038	0.037*
C17	−0.3564 (4)	0.7547 (3)	0.73040 (19)	0.0728 (9)
H17A	−0.3732	0.7958	0.6771	0.109*
H17B	−0.4484	0.8118	0.7581	0.109*
H17C	−0.3968	0.6562	0.7436	0.109*
C18	0.3517 (5)	0.8457 (3)	0.49803 (14)	0.0692 (8)
H18A	0.2633	0.9177	0.5174	0.104*
H18B	0.3815	0.8837	0.4450	0.104*
H18C	0.4862	0.8219	0.5241	0.104*
C19	0.2340 (3)	0.7118 (2)	0.50981 (10)	0.0397 (5)
H19	0.3278	0.6407	0.4894	0.048*
C20	0.0285 (4)	0.7429 (3)	0.46754 (13)	0.0653 (7)
H20A	−0.0443	0.6551	0.4762	0.098*
H20B	0.0615	0.7777	0.4144	0.098*
H20C	−0.0642	0.8160	0.4847	0.098*
C21	0.6302 (3)	0.3192 (2)	0.71540 (13)	0.0451 (5)
H21A	0.6587	0.3397	0.6618	0.068*
H21B	0.7101	0.2292	0.7397	0.068*
H21C	0.6746	0.3971	0.7342	0.068*
C22	0.3917 (3)	0.30635 (18)	0.73179 (10)	0.0258 (4)
H22	0.3678	0.2782	0.7868	0.031*
C23	0.3133 (4)	0.1912 (2)	0.69989 (12)	0.0403 (5)
H23A	0.1611	0.1835	0.7123	0.060*
H23B	0.3933	0.0992	0.7209	0.060*
H23C	0.3352	0.2168	0.6459	0.060*

	U11	U22	U33	U12	U13	U23
S	0.0209 (2)	0.0214 (2)	0.0226 (2)	−0.00145 (16)	−0.00392 (16)	−0.00021 (16)
N	0.0227 (7)	0.0221 (7)	0.0195 (7)	−0.0023 (6)	−0.0030 (6)	−0.0038 (5)
O1	0.0315 (7)	0.0229 (6)	0.0347 (7)	−0.0073 (5)	−0.0106 (5)	0.0006 (5)
O2	0.0262 (7)	0.0321 (7)	0.0301 (7)	0.0046 (5)	0.0039 (5)	0.0017 (5)
C1	0.0376 (10)	0.0233 (9)	0.0285 (9)	−0.0014 (8)	−0.0108 (8)	−0.0080 (7)
C2	0.0295 (9)	0.0259 (9)	0.0188 (8)	0.0015 (7)	−0.0014 (7)	−0.0071 (7)
C3	0.0278 (9)	0.0220 (8)	0.0205 (8)	−0.0016 (7)	−0.0050 (7)	−0.0080 (7)
C4	0.0303 (10)	0.0259 (9)	0.0311 (10)	−0.0029 (7)	−0.0014 (8)	−0.0027 (7)
C5	0.0295 (10)	0.0320 (10)	0.0425 (11)	0.0035 (8)	−0.0042 (8)	−0.0094 (8)
C6	0.0482 (13)	0.0290 (10)	0.0352 (11)	0.0106 (9)	−0.0145 (9)	−0.0066 (8)
C7	0.0572 (14)	0.0366 (11)	0.0245 (10)	0.0046 (10)	−0.0016 (9)	0.0027 (8)
C8	0.0372 (11)	0.0354 (10)	0.0223 (9)	0.0011 (8)	0.0012 (8)	−0.0059 (8)
C9	0.0227 (8)	0.0200 (8)	0.0189 (8)	−0.0029 (6)	−0.0058 (6)	−0.0038 (6)
C10	0.0259 (9)	0.0193 (8)	0.0260 (9)	0.0001 (7)	−0.0035 (7)	−0.0056 (7)
C11	0.0333 (10)	0.0205 (8)	0.0265 (9)	0.0056 (7)	−0.0045 (7)	−0.0003 (7)
C12	0.0339 (10)	0.0282 (9)	0.0219 (9)	0.0017 (8)	−0.0053 (7)	−0.0038 (7)
C13	0.0293 (9)	0.0276 (9)	0.0253 (9)	0.0053 (7)	−0.0040 (7)	−0.0097 (7)
C14	0.0230 (9)	0.0201 (8)	0.0247 (8)	−0.0001 (7)	−0.0083 (7)	−0.0065 (7)
C15	0.0812 (19)	0.0319 (12)	0.0736 (17)	−0.0089 (12)	0.0258 (14)	−0.0251 (12)
C16	0.0393 (11)	0.0205 (9)	0.0295 (9)	0.0048 (8)	0.0035 (8)	−0.0037 (7)
C17	0.0355 (13)	0.084 (2)	0.117 (3)	0.0111 (13)	−0.0003 (14)	−0.0659 (19)
C18	0.087 (2)	0.0712 (18)	0.0413 (14)	−0.0245 (15)	0.0178 (13)	0.0033 (12)
C19	0.0517 (13)	0.0381 (11)	0.0227 (9)	0.0129 (9)	0.0010 (9)	−0.0022 (8)
C20	0.0744 (18)	0.0837 (19)	0.0292 (12)	0.0079 (15)	−0.0155 (12)	−0.0012 (12)
C21	0.0329 (11)	0.0404 (12)	0.0580 (14)	0.0097 (9)	−0.0171 (10)	−0.0066 (10)
C22	0.0306 (9)	0.0219 (9)	0.0253 (9)	0.0054 (7)	−0.0095 (7)	−0.0073 (7)
C23	0.0517 (13)	0.0244 (10)	0.0470 (12)	0.0056 (9)	−0.0197 (10)	−0.0126 (9)

S—O1	1.4322 (12)	C13—C14	1.389 (2)
S—O2	1.4382 (13)	C13—H13	0.9500
S—N	1.6597 (14)	C14—C22	1.530 (2)
S—C9	1.7880 (16)	C15—C16	1.518 (3)
N—C1	1.478 (2)	C15—H15A	0.9800
N—C2	1.504 (2)	C15—H15B	0.9800
C1—C2	1.489 (2)	C15—H15C	0.9800
C1—H1A	0.9900	C16—C17	1.503 (3)
C1—H1B	0.9900	C16—H16	1.0000
C2—C3	1.486 (2)	C17—H17A	0.9800
C2—H2	1.0000	C17—H17B	0.9800
C3—C4	1.385 (2)	C17—H17C	0.9800
C3—C8	1.389 (2)	C18—C19	1.519 (3)
C4—C5	1.384 (3)	C18—H18A	0.9800
C4—H4	0.9500	C18—H18B	0.9800
C5—C6	1.382 (3)	C18—H18C	0.9800
C5—H5	0.9500	C19—C20	1.519 (3)
C6—C7	1.378 (3)	C19—H19	1.0000
C6—H6	0.9500	C20—H20A	0.9800
C7—C8	1.390 (3)	C20—H20B	0.9800
C7—H7	0.9500	C20—H20C	0.9800
C8—H8	0.9500	C21—C22	1.528 (3)
C9—C14	1.415 (2)	C21—H21A	0.9800
C9—C10	1.416 (2)	C21—H21B	0.9800
C10—C11	1.396 (2)	C21—H21C	0.9800
C10—C16	1.531 (2)	C22—C23	1.525 (2)
C11—C12	1.385 (2)	C22—H22	1.0000
C11—H11	0.9500	C23—H23A	0.9800
C12—C13	1.384 (2)	C23—H23B	0.9800
C12—C19	1.520 (2)	C23—H23C	0.9800
O1—S—O2	116.59 (8)	C9—C14—C22	125.91 (15)
O1—S—N	105.66 (7)	C16—C15—H15A	109.5
O2—S—N	111.07 (7)	C16—C15—H15B	109.5
O1—S—C9	108.62 (7)	H15A—C15—H15B	109.5
O2—S—C9	111.50 (7)	C16—C15—H15C	109.5
N—S—C9	102.29 (7)	H15A—C15—H15C	109.5
C1—N—C2	59.91 (11)	H15B—C15—H15C	109.5
C1—N—S	118.58 (11)	C17—C16—C15	112.2 (2)
C2—N—S	113.79 (11)	C17—C16—C10	111.28 (16)
N—C1—C2	60.94 (10)	C15—C16—C10	111.45 (16)
N—C1—H1A	117.7	C17—C16—H16	107.2
C2—C1—H1A	117.7	C15—C16—H16	107.2
N—C1—H1B	117.7	C10—C16—H16	107.2
C2—C1—H1B	117.7	C16—C17—H17A	109.5
H1A—C1—H1B	114.8	C16—C17—H17B	109.5
C3—C2—C1	124.07 (16)	H17A—C17—H17B	109.5
C3—C2—N	115.58 (13)	C16—C17—H17C	109.5
C1—C2—N	59.15 (10)	H17A—C17—H17C	109.5
C3—C2—H2	115.3	H17B—C17—H17C	109.5
C1—C2—H2	115.3	C19—C18—H18A	109.5
N—C2—H2	115.3	C19—C18—H18B	109.5
C4—C3—C8	119.08 (16)	H18A—C18—H18B	109.5
C4—C3—C2	121.46 (15)	C19—C18—H18C	109.5
C8—C3—C2	119.45 (16)	H18A—C18—H18C	109.5
C5—C4—C3	120.59 (17)	H18B—C18—H18C	109.5
C5—C4—H4	119.7	C20—C19—C18	111.1 (2)
C3—C4—H4	119.7	C20—C19—C12	111.87 (18)
C6—C5—C4	120.28 (18)	C18—C19—C12	110.91 (17)
C6—C5—H5	119.9	C20—C19—H19	107.6
C4—C5—H5	119.9	C18—C19—H19	107.6
C7—C6—C5	119.43 (18)	C12—C19—H19	107.6
C7—C6—H6	120.3	C19—C20—H20A	109.5
C5—C6—H6	120.3	C19—C20—H20B	109.5
C6—C7—C8	120.63 (18)	H20A—C20—H20B	109.5
C6—C7—H7	119.7	C19—C20—H20C	109.5
C8—C7—H7	119.7	H20A—C20—H20C	109.5
C3—C8—C7	119.96 (18)	H20B—C20—H20C	109.5
C3—C8—H8	120.0	C22—C21—H21A	109.5
C7—C8—H8	120.0	C22—C21—H21B	109.5
C14—C9—C10	121.29 (15)	H21A—C21—H21B	109.5
C14—C9—S	116.84 (12)	C22—C21—H21C	109.5
C10—C9—S	121.69 (12)	H21A—C21—H21C	109.5
C11—C10—C9	117.04 (15)	H21B—C21—H21C	109.5
C11—C10—C16	116.07 (14)	C23—C22—C21	111.22 (16)
C9—C10—C16	126.88 (15)	C23—C22—C14	110.57 (14)
C12—C11—C10	123.22 (15)	C21—C22—C14	110.51 (15)
C12—C11—H11	118.4	C23—C22—H22	108.1
C10—C11—H11	118.4	C21—C22—H22	108.1
C13—C12—C11	117.74 (16)	C14—C22—H22	108.1
C13—C12—C19	121.16 (16)	C22—C23—H23A	109.5
C11—C12—C19	121.07 (16)	C22—C23—H23B	109.5
C12—C13—C14	123.04 (16)	H23A—C23—H23B	109.5
C12—C13—H13	118.5	C22—C23—H23C	109.5
C14—C13—H13	118.5	H23A—C23—H23C	109.5
C13—C14—C9	117.56 (15)	H23B—C23—H23C	109.5
C13—C14—C22	116.53 (15)

Atom	Deviation
C9	0.020 (1)
C10	-0.013 (1)
C11	-0.005 (1)
C12	0.015 (1)
C13	-0.009 (1)
C14	-0.009 (1)
S1*	0.228 (2)