4,7-Bis­(tri­methyl­silyl­ethynyl)-2,1,3-benzo­thia­diazo­le

The title compound, C₁₆H₂₀N₂SSi₂ is a rigid-rod protected dialkyne. It is used as a model species for platinum-containing compounds of which it is a precursor. Such compounds are of interest due to the extended π-conjugation exhibited through the heteroaromatic linker unit in the backbone. The mol­ecule is pseudo-linear, with a planar central benzo­thia­diazo­le group.

Key indicators

• Single-crystal X-ray study
• T = 170 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.045
• wR factor = 0.116
• Data-to-parameter ratio = 13.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



PLAT_371  Alert C Long   C(sp2)-C(sp1) Bond  C(9)   -   C(12)  =       1.44 Ang.

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #      3
                   C2  -SI1 -C4  -C5     18.00  0.00   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #      4
                   C1  -SI1 -C4  -C5      7.00  0.00   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #      5
                   C3  -SI1 -C4  -C5      5.00  0.00   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #      6
                   SI1 -C4  -C5  -C6      3.00  0.00   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #      9
                   SI1'-C4' -C5' -C6   -179.00 12.00   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #     10
                   C4' -C5' -C6  -C7      6.00  0.00   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #     11
                   C4' -C5' -C6  -C11    14.00  0.00   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #     12
                   C4' -C5' -C6  -C5    -28.00 14.00   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #     13
                   C4  -C5  -C6  -C7     12.00  0.00   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #     14
                   C4  -C5  -C6  -C5'     1.00  0.00   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #     15
                   C4  -C5  -C6  -C11     7.00  0.00   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #     40
                   C8  -C9  -C12 -C13   -33.00  3.00   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #     41
                   C10 -C9  -C12 -C13   145.00  3.00   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #     42
                   C9  -C12 -C13 -SI2   -14.00  6.00   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #     43
                   C14 -SI2 -C13 -C12    38.00  3.00   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #     44
                   C16 -SI2 -C13 -C12   -83.00  3.00   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #     45
                   C15 -SI2 -C13 -C12   157.00  3.00   1.555   1.555   1.555   1.555


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 18 Alert Level C = Please check

---

Computing details

Data collection: COLLECT (Nonius, 1997); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(I)

Crystal data

C16H20N2SSi2	F(000) = 696
Mr = 328.58	Dx = 1.159 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 17.623 (3) Å	Cell parameters from 9092 reflections
b = 5.7385 (6) Å	θ = 2.9–25.0°
c = 20.089 (4) Å	µ = 0.30 mm^−1
β = 112.061 (2)°	T = 170 K
V = 1882.9 (5) Å^3	Plate, pale yellow
Z = 4	0.23 × 0.18 × 0.09 mm

Data collection

Nonius KappaCCD diffractometer	Rint = 0.026
116 1.9° images scans	θmax = 25.1°, θmin = 3.7°
5933 measured reflections	h = −20→20
3293 independent reflections	k = −5→6
2565 reflections with I > 2σ(I)	l = −23→22

Refinement

Refinement on F^2	153 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.045	w = 1/[σ^2(Fo^2) + (0.0503P)^2 + 0.8463P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.116	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.22 e Å^−3
3293 reflections	Δρmin = −0.31 e Å^−3
243 parameters

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.44860 (4)	0.29224 (11)	0.05107 (3)	0.0503 (2)
N1	0.44050 (11)	0.2923 (3)	−0.03182 (9)	0.0428 (4)
N2	0.39124 (11)	0.0737 (3)	0.05176 (10)	0.0447 (5)
Si2	0.18511 (4)	−0.59538 (11)	0.08332 (3)	0.0467 (2)
Si1	0.43559 (8)	0.4803 (2)	−0.29240 (6)	0.0449 (3)	0.6
C1	0.5337 (4)	0.6211 (17)	−0.2390 (4)	0.114 (4)	0.6
H1A	0.5239	0.7489	−0.2109	0.171*	0.6
H1B	0.559	0.6829	−0.2713	0.171*	0.6
H1C	0.5704	0.5065	−0.2065	0.171*	0.6
C2	0.3562 (3)	0.6993 (6)	−0.3370 (2)	0.0504 (10)	0.6
H2A	0.3029	0.622	−0.3587	0.076*	0.6
H2B	0.3695	0.7787	−0.3744	0.076*	0.6
H2C	0.3539	0.8135	−0.3015	0.076*	0.6
C3	0.44912 (19)	0.2761 (5)	−0.36059 (16)	0.0712 (8)	0.6
H3A	0.49	0.1575	−0.3359	0.107*	0.6
H3B	0.4675	0.3644	−0.3935	0.107*	0.6
H3C	0.3968	0.2002	−0.3878	0.107*	0.6
C4	0.4032 (4)	0.3100 (13)	−0.2306 (5)	0.0431 (16)	0.6
C5	0.3837 (7)	0.192 (3)	−0.1890 (9)	0.037 (2)	0.6
Si1'	0.48653 (14)	0.3881 (3)	−0.26928 (11)	0.0530 (5)	0.4
C1'	0.4755 (12)	0.7007 (18)	−0.2668 (9)	0.165 (7)	0.4
H1D	0.4921	0.7522	−0.2168	0.248*	0.4
H1E	0.4181	0.7435	−0.2934	0.248*	0.4
H1F	0.5101	0.7761	−0.2888	0.248*	0.4
C2'	0.5949 (4)	0.3016 (17)	−0.2229 (4)	0.088 (3)	0.4
H2D	0.6274	0.3628	−0.2493	0.131*	0.4
H2E	0.5989	0.1312	−0.2208	0.131*	0.4
H2F	0.6158	0.3649	−0.174	0.131*	0.4
C3'	0.44912 (19)	0.2761 (5)	−0.36059 (16)	0.0712 (8)	0.4
H3D	0.3922	0.3254	−0.3858	0.107*	0.4
H3E	0.4519	0.1055	−0.3594	0.107*	0.4
H3F	0.483	0.337	−0.3857	0.107*	0.4
C4'	0.4291 (7)	0.2492 (17)	−0.2191 (7)	0.044 (2)	0.4
C5'	0.4048 (11)	0.157 (5)	−0.1790 (14)	0.040 (3)	0.4
C6	0.36533 (14)	0.0481 (4)	−0.13710 (12)	0.0453 (5)
C7	0.31601 (16)	−0.1439 (5)	−0.15841 (13)	0.0607 (7)
H7	0.2996	−0.1948	−0.2068	0.073*
C8	0.28854 (17)	−0.2695 (4)	−0.11123 (14)	0.0612 (7)
H8	0.2549	−0.4025	−0.129	0.073*
C9	0.30866 (14)	−0.2066 (4)	−0.04080 (12)	0.0459 (5)
C10	0.36203 (12)	−0.0114 (4)	−0.01546 (11)	0.0381 (5)
C11	0.39001 (12)	0.1142 (4)	−0.06346 (11)	0.0376 (5)
C12	0.27554 (14)	−0.3305 (4)	0.00449 (12)	0.0476 (6)
C13	0.24292 (15)	−0.4364 (4)	0.03809 (13)	0.0503 (6)
C14	0.1070 (2)	−0.7701 (6)	0.01510 (15)	0.0827 (10)
H14A	0.0736	−0.6687	−0.0242	0.124*
H14B	0.072	−0.8461	0.0367	0.124*
H14C	0.1337	−0.8889	−0.0036	0.124*
C15	0.25396 (19)	−0.7917 (6)	0.15268 (17)	0.0897 (11)
H15A	0.2786	−0.9043	0.1301	0.135*
H15B	0.2226	−0.8749	0.1764	0.135*
H15C	0.2972	−0.6999	0.1883	0.135*
C16	0.1387 (3)	−0.3816 (6)	0.1249 (2)	0.1056 (13)
H16A	0.1815	−0.2803	0.1572	0.158*
H16B	0.1111	−0.4636	0.1523	0.158*
H16C	0.0987	−0.2871	0.0874	0.158*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0502 (4)	0.0626 (4)	0.0387 (3)	−0.0102 (3)	0.0175 (3)	−0.0031 (3)
N1	0.0407 (10)	0.0507 (11)	0.0395 (10)	−0.0050 (8)	0.0178 (8)	0.0026 (8)
N2	0.0443 (10)	0.0540 (11)	0.0393 (11)	0.0015 (9)	0.0196 (9)	0.0058 (9)
Si2	0.0546 (4)	0.0489 (4)	0.0423 (4)	−0.0157 (3)	0.0248 (3)	0.0006 (3)
Si1	0.0462 (7)	0.0526 (7)	0.0425 (7)	−0.0010 (6)	0.0243 (5)	0.0128 (5)
C1	0.076 (4)	0.186 (9)	0.070 (4)	−0.075 (5)	0.016 (3)	0.030 (5)
C2	0.076 (3)	0.036 (2)	0.049 (2)	−0.0022 (19)	0.035 (2)	0.0023 (17)
C3	0.087 (2)	0.0801 (19)	0.0645 (18)	0.0181 (16)	0.0492 (17)	0.0221 (15)
C4	0.045 (4)	0.045 (4)	0.040 (4)	0.001 (3)	0.018 (3)	0.008 (3)
C5	0.027 (5)	0.050 (5)	0.031 (5)	−0.005 (4)	0.009 (4)	0.005 (3)
Si1'	0.0751 (14)	0.0474 (10)	0.0527 (11)	−0.0081 (10)	0.0425 (11)	0.0039 (8)
C1'	0.32 (2)	0.060 (6)	0.231 (17)	−0.006 (10)	0.239 (17)	0.007 (8)
C2'	0.062 (4)	0.134 (7)	0.068 (5)	−0.035 (5)	0.026 (4)	−0.005 (5)
C3'	0.087 (2)	0.0801 (19)	0.0645 (18)	0.0181 (16)	0.0492 (17)	0.0221 (15)
C4'	0.050 (7)	0.047 (6)	0.034 (5)	−0.001 (4)	0.016 (5)	0.009 (4)
C5'	0.033 (8)	0.057 (7)	0.025 (6)	0.002 (6)	0.005 (6)	0.006 (5)
C6	0.0494 (13)	0.0521 (13)	0.0393 (12)	−0.0099 (10)	0.0221 (11)	0.0020 (10)
C7	0.0779 (18)	0.0709 (17)	0.0401 (13)	−0.0301 (14)	0.0298 (13)	−0.0092 (12)
C8	0.0786 (18)	0.0581 (16)	0.0545 (16)	−0.0305 (13)	0.0337 (14)	−0.0064 (12)
C9	0.0509 (13)	0.0468 (13)	0.0458 (13)	−0.0049 (10)	0.0249 (11)	0.0075 (10)
C10	0.0372 (11)	0.0443 (12)	0.0365 (12)	0.0047 (9)	0.0180 (9)	0.0063 (9)
C11	0.0361 (11)	0.0425 (12)	0.0375 (12)	−0.0012 (9)	0.0175 (9)	0.0051 (9)
C12	0.0513 (13)	0.0488 (13)	0.0461 (13)	−0.0056 (11)	0.0223 (11)	0.0064 (11)
C13	0.0558 (14)	0.0509 (14)	0.0476 (14)	−0.0070 (11)	0.0234 (12)	0.0049 (11)
C14	0.090 (2)	0.100 (2)	0.0531 (17)	−0.0446 (18)	0.0208 (16)	−0.0035 (16)
C15	0.074 (2)	0.114 (3)	0.072 (2)	−0.0226 (19)	0.0173 (17)	0.0400 (19)
C16	0.153 (3)	0.065 (2)	0.156 (4)	−0.025 (2)	0.124 (3)	−0.016 (2)

Geometric parameters (Å, º)

S1—N2	1.6141 (19)	C1'—H1E	0.9800
S1—N1	1.6169 (19)	C1'—H1F	0.9800
N1—C11	1.348 (3)	C2'—H2D	0.9800
N2—C10	1.344 (3)	C2'—H2E	0.9800
Si2—C14	1.833 (3)	C2'—H2F	0.9800
Si2—C16	1.840 (3)	C4'—C5'	1.17 (3)
Si2—C13	1.842 (2)	C5'—C6	1.42 (3)
Si2—C15	1.847 (3)	C6—C7	1.369 (3)
Si1—C4	1.832 (10)	C6—C11	1.428 (3)
Si1—C2	1.843 (4)	C7—C8	1.413 (3)
Si1—C1	1.844 (6)	C7—H7	0.9500
Si1—C3	1.885 (3)	C8—C9	1.371 (3)
C1—H1A	0.9800	C8—H8	0.9500
C1—H1B	0.9800	C9—C10	1.428 (3)
C1—H1C	0.9800	C9—C12	1.440 (3)
C2—H2A	0.9800	C10—C11	1.432 (3)
C2—H2B	0.9800	C12—C13	1.203 (3)
C2—H2C	0.9800	C14—H14A	0.9800
C3—H3A	0.9800	C14—H14B	0.9800
C3—H3B	0.9800	C14—H14C	0.9800
C3—H3C	0.9800	C15—H15A	0.9800
C4—C5	1.219 (19)	C15—H15B	0.9800
C5—C6	1.460 (18)	C15—H15C	0.9800
Si1'—C1'	1.808 (11)	C16—H16A	0.9800
Si1'—C2'	1.851 (8)	C16—H16B	0.9800
Si1'—C4'	1.855 (14)	C16—H16C	0.9800
C1'—H1D	0.9800
N2—S1—N1	101.28 (9)	C7—C6—C5	121.2 (7)
C11—N1—S1	105.85 (14)	C11—C6—C5	121.8 (7)
C10—N2—S1	106.18 (14)	C6—C7—C8	122.6 (2)
C14—Si2—C16	111.54 (18)	C6—C7—H7	118.7
C14—Si2—C13	107.53 (12)	C8—C7—H7	118.7
C16—Si2—C13	108.45 (12)	C9—C8—C7	122.5 (2)
C14—Si2—C15	109.06 (16)	C9—C8—H8	118.8
C16—Si2—C15	110.00 (19)	C7—C8—H8	118.8
C13—Si2—C15	110.24 (13)	C8—C9—C10	117.03 (19)
C4—Si1—C2	108.7 (2)	C8—C9—C12	120.9 (2)
C4—Si1—C1	107.6 (3)	C10—C9—C12	122.1 (2)
C2—Si1—C1	111.0 (3)	N2—C10—C9	126.57 (19)
C4—Si1—C3	108.5 (3)	N2—C10—C11	113.28 (19)
C2—Si1—C3	110.53 (16)	C9—C10—C11	120.15 (19)
C1—Si1—C3	110.4 (3)	N1—C11—C6	125.49 (18)
C5—C4—Si1	178.0 (7)	N1—C11—C10	113.42 (19)
C4—C5—C6	176.7 (9)	C6—C11—C10	121.09 (19)
C1'—Si1'—C2'	110.7 (7)	C13—C12—C9	175.4 (3)
C1'—Si1'—C4'	109.0 (5)	C12—C13—Si2	175.4 (2)
C2'—Si1'—C4'	106.4 (4)	Si2—C14—H14A	109.5
Si1'—C1'—H1D	109.5	Si2—C14—H14B	109.5
Si1'—C1'—H1E	109.5	H14A—C14—H14B	109.5
H1D—C1'—H1E	109.5	Si2—C14—H14C	109.5
Si1'—C1'—H1F	109.5	H14A—C14—H14C	109.5
H1D—C1'—H1F	109.5	H14B—C14—H14C	109.5
H1E—C1'—H1F	109.5	Si2—C15—H15A	109.5
Si1'—C2'—H2D	109.5	Si2—C15—H15B	109.5
Si1'—C2'—H2E	109.5	H15A—C15—H15B	109.5
H2D—C2'—H2E	109.5	Si2—C15—H15C	109.5
Si1'—C2'—H2F	109.5	H15A—C15—H15C	109.5
H2D—C2'—H2F	109.5	H15B—C15—H15C	109.5
H2E—C2'—H2F	109.5	Si2—C16—H16A	109.5
C5'—C4'—Si1'	169.4 (12)	Si2—C16—H16B	109.5
C4'—C5'—C6	172.8 (16)	H16A—C16—H16B	109.5
C7—C6—C5'	124.3 (12)	Si2—C16—H16C	109.5
C7—C6—C11	116.6 (2)	H16A—C16—H16C	109.5
C5'—C6—C11	118.0 (11)	H16B—C16—H16C	109.5
N2—S1—N1—C11	0.35 (16)	C8—C9—C10—N2	−177.7 (2)
N1—S1—N2—C10	−0.16 (16)	C12—C9—C10—N2	3.6 (3)
C2—Si1—C4—C5	18E1 (10)	C8—C9—C10—C11	2.0 (3)
C1—Si1—C4—C5	−7E1 (3)	C12—C9—C10—C11	−176.7 (2)
C3—Si1—C4—C5	5E1 (3)	S1—N1—C11—C6	−179.93 (19)
Si1—C4—C5—C6	3E1 (6)	S1—N1—C11—C10	−0.4 (2)
C1'—Si1'—C4'—C5'	−103 (9)	C7—C6—C11—N1	177.6 (2)
C2'—Si1'—C4'—C5'	17 (9)	C5'—C6—C11—N1	8.8 (9)
Si1'—C4'—C5'—C6	−179 (12)	C5—C6—C11—N1	−9.2 (6)
C4'—C5'—C6—C7	6E1 (2)	C7—C6—C11—C10	−1.9 (3)
C4'—C5'—C6—C11	−14E1 (2)	C5'—C6—C11—C10	−170.7 (8)
C4'—C5'—C6—C5	−28 (14)	C5—C6—C11—C10	171.3 (5)
C4—C5—C6—C7	−12E1 (3)	N2—C10—C11—N1	0.4 (3)
C4—C5—C6—C5'	−1E1 (2)	C9—C10—C11—N1	−179.41 (19)
C4—C5—C6—C11	7E1 (3)	N2—C10—C11—C6	179.88 (19)
C5'—C6—C7—C8	169.6 (8)	C9—C10—C11—C6	0.1 (3)
C11—C6—C7—C8	1.5 (4)	C8—C9—C12—C13	−33 (3)
C5—C6—C7—C8	−171.7 (6)	C10—C9—C12—C13	145 (3)
C6—C7—C8—C9	0.7 (5)	C9—C12—C13—Si2	−14 (6)
C7—C8—C9—C10	−2.5 (4)	C14—Si2—C13—C12	38 (3)
C7—C8—C9—C12	176.3 (3)	C16—Si2—C13—C12	−83 (3)
S1—N2—C10—C9	179.67 (18)	C15—Si2—C13—C12	157 (3)
S1—N2—C10—C11	−0.1 (2)