p-Tolyl­sulfonyl cyanide

The first crystal structure of a sulfonyl cyanide, C₈H₇NO₂S, has been determined. The mol­ecule has an unusual bond-length distribution, with a very long S-Csp bond [1.772 (2) Å] and a short S-Csp² bond [1.7368 (17) Å].

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.045
• wR factor = 0.130
• Data-to-parameter ratio = 18.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

p-toluenesulfonyl cyanide

Crystal data

C8H7NO2S	Dx = 1.424 Mg m^−3
Mr = 181.21	Melting point: 48°C K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 6.5810 (4) Å	Cell parameters from 1807 reflections
b = 15.377 (1) Å	θ = 2.8–30.5°
c = 8.3671 (5) Å	µ = 0.34 mm^−1
β = 93.49 (1)°	T = 120 K
V = 845.15 (9) Å^3	Prism, colourless
Z = 4	0.40 × 0.18 × 0.10 mm
F(000) = 376

Data collection

Bruker SMART 6000 diffractometer	1742 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.051
Graphite monochromator	θmax = 30.5°, θmin = 2.7°
Detector resolution: 8 pixels mm^-1	h = −8→9
ω scans	k = −21→21
6296 measured reflections	l = −11→11
2542 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: difference Fourier map
wR(F^2) = 0.130	All H-atom parameters refined
S = 0.97	w = 1/[σ^2(Fo^2) + (0.075P)^2] where P = (Fo^2 + 2Fc^2)/3
2542 reflections	(Δ/σ)max = 0.001
137 parameters	Δρmax = 0.46 e Å^−3
0 restraints	Δρmin = −0.37 e Å^−3

Special details

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.

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 > σ(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 (Ų)

	x	y	z	Uiso*/Ueq
S1	1.18519 (7)	0.60506 (3)	0.35505 (5)	0.03158 (16)
O1	1.0607 (2)	0.53021 (8)	0.32912 (17)	0.0431 (4)
O2	1.3344 (2)	0.62846 (10)	0.24654 (17)	0.0444 (4)
N1	1.4228 (3)	0.57551 (11)	0.6538 (2)	0.0436 (4)
C1	1.0421 (3)	0.69537 (11)	0.4023 (2)	0.0270 (4)
C2	0.8574 (3)	0.68434 (12)	0.4720 (2)	0.0328 (4)
C3	0.7475 (3)	0.75796 (12)	0.5081 (2)	0.0328 (4)
C4	0.8175 (3)	0.84086 (11)	0.4740 (2)	0.0276 (4)
C5	1.0032 (3)	0.84929 (11)	0.4039 (2)	0.0314 (4)
C6	1.1172 (3)	0.77714 (11)	0.3683 (2)	0.0309 (4)
C7	0.6962 (3)	0.91988 (13)	0.5144 (3)	0.0350 (4)
C8	1.3263 (3)	0.58573 (11)	0.5387 (2)	0.0312 (4)
H2	0.813 (3)	0.6252 (14)	0.495 (3)	0.042 (6)*
H3	0.623 (4)	0.7520 (15)	0.554 (3)	0.049 (6)*
H5	1.045 (3)	0.9052 (14)	0.379 (3)	0.040 (6)*
H6	1.251 (3)	0.7850 (12)	0.322 (2)	0.033 (5)*
H71	0.730 (4)	0.9669 (17)	0.455 (3)	0.064 (8)*
H72	0.550 (4)	0.9084 (16)	0.492 (3)	0.063 (8)*
H73	0.730 (5)	0.9373 (19)	0.621 (4)	0.080 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0379 (3)	0.0280 (2)	0.0287 (2)	0.00621 (17)	0.00065 (19)	−0.00357 (16)
O1	0.0485 (8)	0.0294 (7)	0.0502 (9)	0.0028 (6)	−0.0068 (7)	−0.0120 (6)
O2	0.0514 (8)	0.0469 (8)	0.0365 (8)	0.0134 (7)	0.0166 (7)	0.0010 (6)
N1	0.0438 (10)	0.0425 (10)	0.0437 (10)	0.0077 (8)	−0.0029 (9)	0.0003 (8)
C1	0.0303 (8)	0.0252 (8)	0.0254 (8)	0.0024 (6)	0.0005 (7)	0.0003 (6)
C2	0.0339 (9)	0.0244 (8)	0.0402 (10)	−0.0019 (7)	0.0030 (8)	0.0018 (7)
C3	0.0300 (9)	0.0294 (9)	0.0398 (10)	0.0001 (7)	0.0079 (8)	0.0026 (7)
C4	0.0327 (9)	0.0252 (8)	0.0246 (7)	0.0044 (7)	−0.0012 (7)	0.0010 (6)
C5	0.0365 (9)	0.0250 (9)	0.0330 (9)	−0.0007 (7)	0.0040 (8)	0.0045 (7)
C6	0.0322 (9)	0.0289 (9)	0.0319 (9)	0.0010 (7)	0.0046 (8)	0.0049 (7)
C7	0.0415 (11)	0.0283 (9)	0.0354 (10)	0.0064 (8)	0.0033 (9)	−0.0002 (8)
C8	0.0331 (9)	0.0247 (8)	0.0358 (9)	0.0046 (7)	0.0038 (8)	−0.0015 (7)

Geometric parameters (Å, º)

S1—O1	1.4217 (14)	C3—H3	0.93 (2)
S1—O2	1.4234 (14)	C4—C5	1.394 (2)
S1—C1	1.7368 (17)	C4—C7	1.503 (2)
S1—C8	1.772 (2)	C5—C6	1.382 (2)
N1—C8	1.132 (2)	C5—H5	0.93 (2)
C1—C6	1.387 (2)	C6—H6	0.993 (19)
C1—C2	1.390 (3)	C7—H71	0.91 (3)
C2—C3	1.387 (2)	C7—H72	0.99 (3)
C2—H2	0.98 (2)	C7—H73	0.95 (3)
C3—C4	1.391 (2)
O1—S1—O2	121.38 (9)	C3—C4—C7	120.52 (16)
O1—S1—C1	111.51 (9)	C5—C4—C7	120.70 (16)
O2—S1—C1	110.34 (8)	C6—C5—C4	121.17 (16)
O1—S1—C8	105.26 (9)	C6—C5—H5	121.7 (13)
O2—S1—C8	104.50 (9)	C4—C5—H5	117.1 (13)
C1—S1—C8	101.49 (8)	C5—C6—C1	118.62 (17)
C6—C1—C2	121.88 (16)	C5—C6—H6	119.5 (11)
C6—C1—S1	118.26 (13)	C1—C6—H6	121.8 (11)
C2—C1—S1	119.86 (13)	C4—C7—H71	111.6 (17)
C3—C2—C1	118.22 (16)	C4—C7—H72	109.8 (15)
C3—C2—H2	123.5 (12)	H71—C7—H72	108 (2)
C1—C2—H2	118.3 (12)	C4—C7—H73	110.0 (18)
C2—C3—C4	121.33 (17)	H71—C7—H73	104 (2)
C2—C3—H3	119.6 (15)	H72—C7—H73	114 (2)
C4—C3—H3	119.1 (15)	N1—C8—S1	177.09 (18)
C3—C4—C5	118.78 (16)
O1—S1—C1—C6	−154.26 (14)	C1—C2—C3—C4	0.9 (3)
O2—S1—C1—C6	−16.26 (17)	C2—C3—C4—C5	−0.8 (3)
C8—S1—C1—C6	94.10 (15)	C2—C3—C4—C7	−179.90 (18)
O1—S1—C1—C2	25.57 (18)	C3—C4—C5—C6	0.1 (3)
O2—S1—C1—C2	163.56 (15)	C7—C4—C5—C6	179.15 (17)
C8—S1—C1—C2	−86.08 (16)	C4—C5—C6—C1	0.6 (3)
C6—C1—C2—C3	−0.2 (3)	C2—C1—C6—C5	−0.5 (3)
S1—C1—C2—C3	179.97 (14)	S1—C1—C6—C5	179.32 (14)