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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].
Supporting information
CCDC reference: 180805
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (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
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
top
Crystal data top
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) Å3 | Prism, colourless |
Z = 4 | 0.40 × 0.18 × 0.10 mm |
F(000) = 376 | |
Data collection top
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 top
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)] = 0.045 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.130 | All H-atom parameters refined |
S = 0.97 | w = 1/[σ2(Fo2) + (0.075P)2] where P = (Fo2 + 2Fc2)/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 top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) |
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