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The title compound, 4-(4-methylphenyl)-1,3-diaza-2,4-dithiabuta-1,2-diene, C7H8N2S2, was the first example of a stable monosubstituted sulfur diimide to be documented [Jones (1988). PhD thesis, Imperial College, University of London, England]. Although a partial description of this structure was published previously, the full details are presented here. This allows a detailed comparison against the only other example of this system published to date, highlighting differences in bonding, conformation and packing.
Supporting information
CCDC reference: 1062886
Data collection: Nicolet software; cell refinement: Nicolet software; data reduction: Nicolet software; program(s) used to solve structure: SHELXTL83 (Sheldrick, 1983) and SHELXLE (Hübschle et al., 2011); program(s) used to refine structure: SHELXTL83 (Sheldrick, 1983) and SHELXL2013 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2008) and OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2015).
4-(4-Methylphenyl)-1,3-diaza-2,4-dithiabuta-1,2-diene
top
Crystal data top
C7H8N2S2 | Z = 4 |
Mr = 184.27 | F(000) = 384 |
Orthorhombic, P212121 | Dx = 1.389 Mg m−3 |
a = 6.223 (1) Å | Cu Kα radiation, λ = 1.54178 Å |
b = 7.178 (2) Å | µ = 4.96 mm−1 |
c = 19.732 (5) Å | T = 293 K |
V = 881.4 (4) Å3 | 0.35 × 0.10 × 0.05 mm |
Data collection top
Scintillation diffractometer | θmax = 57.0°, θmin = 4.5° |
Absorption correction: empirical (using intensity measurements) psi scans | h = 0→6 |
Tmin = 0.55, Tmax = 0.78 | k = 0→7 |
647 independent reflections | l = 0→21 |
603 reflections with I > 2σ(I) | |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.037 | w = 1/[σ2(Fo2) + (0.011P)2 + 1.0000sinθ] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.065 | (Δ/σ)max < 0.001 |
S = 1.00 | Δρmax = 0.13 e Å−3 |
647 reflections | Δρmin = −0.15 e Å−3 |
105 parameters | Absolute structure: No quotients, so Flack parameter determined by classical intensity fit. |
1 restraint | Absolute structure parameter: 0.20 (8) |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 1.0675 (9) | 0.7290 (10) | 0.4722 (2) | 0.0875 (18) | |
H1N | 1.168 (6) | 0.714 (11) | 0.502 (2) | 0.11 (2)* | |
S2 | 1.1895 (3) | 0.8023 (3) | 0.41043 (8) | 0.0845 (5) | |
N3 | 1.0517 (7) | 0.7902 (7) | 0.3456 (2) | 0.0755 (14) | |
S4 | 0.8085 (2) | 0.7014 (2) | 0.34886 (7) | 0.0650 (4) | |
C1 | 0.7322 (8) | 0.7226 (8) | 0.2630 (2) | 0.0511 (13) | |
C2 | 0.8628 (8) | 0.7917 (8) | 0.2129 (2) | 0.0584 (14) | |
H2 | 1.0023 | 0.8288 | 0.2231 | 0.070* | |
C3 | 0.7868 (9) | 0.8060 (8) | 0.1478 (3) | 0.0621 (14) | |
H3 | 0.8760 | 0.8539 | 0.1143 | 0.075* | |
C4 | 0.5811 (9) | 0.7510 (9) | 0.1310 (3) | 0.0634 (17) | |
C5 | 0.4541 (9) | 0.6771 (9) | 0.1813 (3) | 0.0682 (17) | |
H5 | 0.3161 | 0.6366 | 0.1708 | 0.082* | |
C6 | 0.5276 (9) | 0.6617 (8) | 0.2472 (3) | 0.0602 (15) | |
H6 | 0.4401 | 0.6108 | 0.2806 | 0.072* | |
C7 | 0.4947 (10) | 0.7683 (10) | 0.0588 (2) | 0.091 (2) | |
H7A | 0.4758 | 0.6463 | 0.0398 | 0.136* | |
H7B | 0.5950 | 0.8374 | 0.0317 | 0.136* | |
H7C | 0.3592 | 0.8321 | 0.0596 | 0.136* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.083 (3) | 0.116 (5) | 0.064 (3) | −0.003 (5) | 0.000 (3) | −0.007 (4) |
S2 | 0.0819 (10) | 0.0866 (11) | 0.0851 (10) | −0.0211 (13) | −0.0108 (10) | 0.0003 (11) |
N3 | 0.073 (3) | 0.073 (3) | 0.080 (3) | −0.025 (3) | −0.010 (3) | 0.017 (3) |
S4 | 0.0606 (8) | 0.0736 (9) | 0.0608 (8) | 0.0030 (10) | 0.0103 (8) | 0.0105 (9) |
C1 | 0.055 (3) | 0.043 (3) | 0.056 (3) | 0.003 (3) | 0.011 (3) | 0.002 (3) |
C2 | 0.054 (3) | 0.054 (3) | 0.067 (3) | 0.001 (3) | 0.007 (3) | 0.006 (3) |
C3 | 0.064 (3) | 0.057 (3) | 0.066 (3) | 0.007 (4) | 0.011 (3) | 0.001 (4) |
C4 | 0.069 (4) | 0.056 (5) | 0.065 (3) | 0.009 (4) | 0.003 (3) | −0.009 (3) |
C5 | 0.053 (3) | 0.064 (4) | 0.087 (4) | −0.007 (4) | 0.004 (3) | −0.019 (4) |
C6 | 0.056 (3) | 0.055 (4) | 0.070 (3) | −0.009 (3) | 0.014 (3) | −0.008 (3) |
C7 | 0.097 (5) | 0.104 (6) | 0.071 (4) | 0.005 (5) | −0.012 (4) | −0.009 (4) |
Geometric parameters (Å, º) top
N1—S2 | 1.530 (5) | C3—H3 | 0.9300 |
N1—H1N | 0.860 (2) | C4—C5 | 1.376 (7) |
S2—N3 | 1.543 (5) | C4—C7 | 1.527 (6) |
N3—S4 | 1.643 (4) | C5—C6 | 1.383 (7) |
S4—C1 | 1.767 (5) | C5—H5 | 0.9300 |
C1—C2 | 1.372 (6) | C6—H6 | 0.9300 |
C1—C6 | 1.381 (7) | C7—H7A | 0.9600 |
C2—C3 | 1.373 (6) | C7—H7B | 0.9600 |
C2—H2 | 0.9300 | C7—H7C | 0.9600 |
C3—C4 | 1.380 (7) | | |
| | | |
S2—N1—H1N | 103 (4) | C5—C4—C7 | 120.2 (6) |
N1—S2—N3 | 111.5 (3) | C3—C4—C7 | 121.8 (6) |
S2—N3—S4 | 120.1 (3) | C4—C5—C6 | 121.3 (5) |
N3—S4—C1 | 100.2 (3) | C4—C5—H5 | 119.4 |
C2—C1—C6 | 119.9 (5) | C6—C5—H5 | 119.4 |
C2—C1—S4 | 124.2 (4) | C1—C6—C5 | 119.4 (5) |
C6—C1—S4 | 115.9 (4) | C1—C6—H6 | 120.3 |
C1—C2—C3 | 119.8 (5) | C5—C6—H6 | 120.3 |
C1—C2—H2 | 120.1 | C4—C7—H7A | 109.5 |
C3—C2—H2 | 120.1 | C4—C7—H7B | 109.5 |
C2—C3—C4 | 121.6 (5) | H7A—C7—H7B | 109.5 |
C2—C3—H3 | 119.2 | C4—C7—H7C | 109.5 |
C4—C3—H3 | 119.2 | H7A—C7—H7C | 109.5 |
C5—C4—C3 | 118.0 (5) | H7B—C7—H7C | 109.5 |
| | | |
N1—S2—N3—S4 | −1.5 (5) | C2—C3—C4—C5 | −1.3 (9) |
S2—N3—S4—C1 | −179.8 (4) | C2—C3—C4—C7 | 179.4 (6) |
N3—S4—C1—C2 | 1.9 (5) | C3—C4—C5—C6 | 1.4 (9) |
N3—S4—C1—C6 | −179.0 (5) | C7—C4—C5—C6 | −179.3 (6) |
C6—C1—C2—C3 | 2.3 (9) | C2—C1—C6—C5 | −2.2 (8) |
S4—C1—C2—C3 | −178.7 (5) | S4—C1—C6—C5 | 178.7 (4) |
C1—C2—C3—C4 | −0.5 (9) | C4—C5—C6—C1 | 0.3 (9) |
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