4,5-Di­cyano-1,2-bis(2-di­methyl­amino­ethyl­sulfanyl)­benzene

The title compound, C₁₆H₂₂N₄S₂, contains a di­cyano­benzene ring and two 2-di­methyl­amino­ethyl­sulfanyl substituents that have a twist conformation. The crystal structure is stabilized by C—H...N and C—H...π interactions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.045
• wR factor = 0.095
• Data-to-parameter ratio = 21.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low ....         38 Perc.

Alert level C
GOODF01_ALERT_2_C  The least squares goodness of fit parameter lies
            outside the range 0.80 <> 2.00
            Goodness of fit given =      0.716
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.80 mm
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....         N3
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....         N4
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C1     -   C8       =       1.42 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C2     -   C3       =       1.43 Ang.

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2001); 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: SHELXL97 and WinGX (Farrugia, 1999).

4,5-Dicyano-1,2-bis(2-dimethylaminoethylsulfanyl)benzene

Crystal data

C16H22N4S2	Dx = 1.196 Mg m^−3
Mr = 334.50	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 7087 reflections
a = 9.5897 (6) Å	θ = 2.1–25.8°
b = 27.024 (2) Å	µ = 0.29 mm^−1
c = 14.3392 (14) Å	T = 293 K
V = 3716.1 (5) Å^3	Lath, pale yellow
Z = 8	0.80 × 0.34 × 0.08 mm
F(000) = 1424

Data collection

Stoe IPDS2 diffractometer	4367 independent reflections
Radiation source: fine-focus sealed tube	1651 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.092
Detector resolution: 6.67 pixels mm^-1	θmax = 27.8°, θmin = 2.1°
ω scans	h = −12→11
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −35→35
Tmin = 0.802, Tmax = 0.977	l = −18→18
26348 measured 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: inferred from neighbouring sites
wR(F^2) = 0.096	H-atom parameters constrained
S = 0.72	w = 1/[σ^2(Fo^2) + (0.0239P)^2] where P = (Fo^2 + 2Fc^2)/3
4367 reflections	(Δ/σ)max = 0.001
199 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.32 e Å^−3

Special details

Experimental. Because the crystal collected datas is very thin, check cif give B type allert "Ratio Observed / Unique Reflections too Low ···. 38 Perc."

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
C11	0.3186 (4)	0.80482 (13)	0.9447 (2)	0.0911 (12)
H11A	0.4145	0.8148	0.9405	0.137*
H11B	0.3099	0.7783	0.9889	0.137*
H11C	0.2629	0.8324	0.9647	0.137*
C12	0.2940 (4)	0.82653 (12)	0.7845 (3)	0.0960 (12)
H12A	0.3908	0.8356	0.7843	0.144*
H12B	0.2384	0.8550	0.7996	0.144*
H12C	0.2681	0.8144	0.7240	0.144*
S1	0.20135 (7)	0.69814 (3)	0.74335 (6)	0.0584 (2)
S2	0.34219 (8)	0.60427 (3)	0.68672 (6)	0.0618 (2)
C5	0.1821 (2)	0.61723 (9)	0.63474 (18)	0.0425 (6)
C7	−0.0070 (3)	0.67568 (9)	0.61607 (19)	0.0466 (7)
H7	−0.0482	0.7058	0.6308	0.056*
C6	0.1154 (2)	0.66256 (9)	0.65893 (18)	0.0413 (6)
C3	−0.0076 (3)	0.59941 (10)	0.52946 (19)	0.0467 (7)
C8	−0.0710 (3)	0.64504 (10)	0.55123 (19)	0.0458 (7)
C4	0.1152 (3)	0.58654 (9)	0.5711 (2)	0.0479 (7)
H4	0.1555	0.5562	0.5563	0.057*
C2	−0.0721 (3)	0.56667 (11)	0.4639 (2)	0.0597 (8)
C14	0.5352 (3)	0.53291 (11)	0.6702 (2)	0.0665 (9)
H14A	0.5998	0.5604	0.6656	0.080*
H14B	0.5229	0.5251	0.7357	0.080*
N3	0.2706 (2)	0.78811 (8)	0.85361 (18)	0.0585 (7)
N4	0.5934 (3)	0.48997 (10)	0.62194 (17)	0.0669 (7)
C1	−0.1962 (3)	0.65976 (11)	0.5059 (2)	0.0619 (8)
C10	0.1271 (3)	0.77267 (11)	0.8570 (2)	0.0672 (9)
H10A	0.0687	0.8014	0.8684	0.081*
H10B	0.1147	0.7500	0.9087	0.081*
C9	0.0794 (3)	0.74742 (11)	0.7672 (2)	0.0673 (9)
H9A	0.0783	0.7709	0.7162	0.081*
H9B	−0.0139	0.7342	0.7749	0.081*
N2	−0.1223 (3)	0.54044 (10)	0.4114 (2)	0.0855 (9)
C13	0.3970 (3)	0.54765 (10)	0.6288 (2)	0.0610 (8)
H13A	0.3287	0.5217	0.6387	0.073*
H13B	0.4064	0.5532	0.5623	0.073*
N1	−0.2961 (3)	0.67096 (12)	0.4685 (2)	0.1016 (11)
C16	0.7342 (3)	0.48091 (14)	0.6532 (3)	0.0896 (12)
H16A	0.7715	0.4528	0.6208	0.134*
H16B	0.7339	0.4745	0.7190	0.134*
H16C	0.7907	0.5094	0.6405	0.134*
C15	0.5080 (4)	0.44650 (12)	0.6367 (3)	0.0959 (12)
H15A	0.5480	0.4189	0.6041	0.144*
H15B	0.4156	0.4526	0.6136	0.144*
H15C	0.5038	0.4392	0.7022	0.144*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C11	0.087 (3)	0.094 (3)	0.093 (3)	0.003 (2)	−0.018 (2)	−0.044 (2)
C12	0.116 (3)	0.067 (2)	0.105 (3)	−0.010 (2)	0.007 (3)	−0.012 (2)
S1	0.0484 (4)	0.0530 (4)	0.0738 (5)	0.0067 (3)	−0.0146 (4)	−0.0246 (4)
S2	0.0572 (4)	0.0491 (4)	0.0790 (6)	0.0095 (4)	−0.0210 (4)	−0.0179 (4)
C5	0.0432 (16)	0.0427 (14)	0.0417 (16)	−0.0045 (12)	−0.0015 (13)	−0.0007 (12)
C7	0.0470 (16)	0.0407 (14)	0.0520 (18)	0.0023 (13)	−0.0001 (15)	−0.0066 (13)
C6	0.0395 (15)	0.0377 (14)	0.0466 (17)	−0.0019 (12)	0.0016 (13)	−0.0044 (12)
C3	0.0449 (16)	0.0491 (16)	0.0462 (18)	−0.0085 (13)	−0.0038 (14)	−0.0060 (14)
C8	0.0409 (16)	0.0540 (17)	0.0425 (17)	0.0003 (13)	−0.0024 (14)	−0.0029 (14)
C4	0.0501 (17)	0.0372 (14)	0.0562 (19)	−0.0027 (13)	−0.0070 (15)	−0.0045 (13)
C2	0.062 (2)	0.0568 (18)	0.061 (2)	−0.0018 (16)	−0.0130 (18)	−0.0067 (17)
C14	0.0578 (18)	0.0698 (19)	0.072 (2)	0.0142 (16)	−0.0101 (17)	−0.0128 (18)
N3	0.0551 (15)	0.0529 (15)	0.0674 (17)	−0.0011 (12)	−0.0007 (14)	−0.0246 (13)
N4	0.0623 (17)	0.0722 (17)	0.0661 (18)	0.0257 (14)	−0.0036 (14)	−0.0108 (15)
C1	0.055 (2)	0.071 (2)	0.059 (2)	0.0067 (16)	−0.0059 (19)	−0.0175 (16)
C10	0.058 (2)	0.0602 (18)	0.084 (2)	0.0060 (15)	0.0020 (18)	−0.0284 (18)
C9	0.0489 (17)	0.0608 (17)	0.092 (3)	0.0092 (14)	−0.0112 (18)	−0.0334 (18)
N2	0.086 (2)	0.0751 (19)	0.095 (2)	−0.0048 (16)	−0.0312 (18)	−0.0239 (18)
C13	0.0640 (19)	0.0525 (16)	0.067 (2)	0.0141 (15)	−0.0089 (17)	−0.0160 (16)
N1	0.078 (2)	0.124 (3)	0.103 (3)	0.0290 (19)	−0.036 (2)	−0.032 (2)
C16	0.070 (2)	0.109 (3)	0.090 (3)	0.034 (2)	−0.001 (2)	−0.014 (2)
C15	0.096 (3)	0.066 (2)	0.125 (3)	0.021 (2)	0.001 (3)	−0.017 (2)

Geometric parameters (Å, º)

C11—N3	1.457 (4)	C2—N2	1.141 (3)
C11—H11A	0.960	C14—N4	1.462 (3)
C11—H11B	0.960	C14—C13	1.505 (3)
C11—H11C	0.960	C14—H14A	0.970
C12—N3	1.452 (4)	C14—H14B	0.970
C12—H12A	0.960	N3—C10	1.439 (3)
C12—H12B	0.960	N4—C16	1.444 (4)
C12—H12C	0.960	N4—C15	1.447 (4)
S1—C6	1.752 (3)	C1—N1	1.138 (4)
S1—C9	1.806 (3)	C10—C9	1.527 (4)
S2—C5	1.742 (3)	C10—H10A	0.970
S2—C13	1.818 (3)	C10—H10B	0.970
C5—C4	1.390 (3)	C9—H9A	0.970
C5—C6	1.425 (3)	C9—H9B	0.970
C7—C6	1.372 (3)	C13—H13A	0.970
C7—C8	1.388 (3)	C13—H13B	0.970
C7—H7	0.930	C16—H16A	0.960
C3—C4	1.365 (3)	C16—H16B	0.960
C3—C8	1.410 (3)	C16—H16C	0.960
C3—C2	1.431 (4)	C15—H15A	0.960
C8—C1	1.423 (4)	C15—H15B	0.960
C4—H4	0.930	C15—H15C	0.960
N3—C11—H11A	109.5	H14A—C14—H14B	108.0
N3—C11—H11B	109.5	C10—N3—C12	112.2 (3)
H11A—C11—H11B	109.5	C10—N3—C11	111.2 (3)
N3—C11—H11C	109.5	C12—N3—C11	110.0 (3)
H11A—C11—H11C	109.5	C16—N4—C15	110.2 (3)
H11B—C11—H11C	109.5	C16—N4—C14	110.2 (2)
N3—C12—H12A	109.5	C15—N4—C14	111.0 (2)
N3—C12—H12B	109.5	N1—C1—C8	178.9 (3)
H12A—C12—H12B	109.5	N3—C10—C9	112.8 (2)
N3—C12—H12C	109.5	N3—C10—H10A	109.0
H12A—C12—H12C	109.5	C9—C10—H10A	109.0
H12B—C12—H12C	109.5	N3—C10—H10B	109.0
C6—S1—C9	103.37 (12)	C9—C10—H10B	109.0
C5—S2—C13	103.21 (12)	H10A—C10—H10B	107.8
C4—C5—C6	117.7 (2)	C10—C9—S1	107.2 (2)
C4—C5—S2	124.6 (2)	C10—C9—H9A	110.3
C6—C5—S2	117.66 (19)	S1—C9—H9A	110.3
C6—C7—C8	121.6 (2)	C10—C9—H9B	110.3
C6—C7—H7	119.2	S1—C9—H9B	110.3
C8—C7—H7	119.2	H9A—C9—H9B	108.5
C7—C6—C5	119.8 (2)	C14—C13—S2	107.3 (2)
C7—C6—S1	124.77 (19)	C14—C13—H13A	110.3
C5—C6—S1	115.40 (19)	S2—C13—H13A	110.3
C4—C3—C8	119.9 (2)	C14—C13—H13B	110.3
C4—C3—C2	120.2 (3)	S2—C13—H13B	110.3
C8—C3—C2	120.0 (3)	H13A—C13—H13B	108.5
C7—C8—C3	118.6 (2)	N4—C16—H16A	109.5
C7—C8—C1	120.8 (2)	N4—C16—H16B	109.5
C3—C8—C1	120.5 (2)	H16A—C16—H16B	109.5
C3—C4—C5	122.2 (2)	N4—C16—H16C	109.5
C3—C4—H4	118.9	H16A—C16—H16C	109.5
C5—C4—H4	118.9	H16B—C16—H16C	109.5
N2—C2—C3	179.4 (4)	N4—C15—H15A	109.5
N4—C14—C13	111.1 (2)	N4—C15—H15B	109.5
N4—C14—H14A	109.4	H15A—C15—H15B	109.5
C13—C14—H14A	109.4	N4—C15—H15C	109.5
N4—C14—H14B	109.4	H15A—C15—H15C	109.5
C13—C14—H14B	109.4	H15B—C15—H15C	109.5
C13—S2—C5—C4	5.3 (3)	C2—C3—C8—C1	−2.4 (4)
C13—S2—C5—C6	−174.5 (2)	C8—C3—C4—C5	−0.4 (4)
C8—C7—C6—C5	2.1 (4)	C2—C3—C4—C5	179.6 (3)
C8—C7—C6—S1	−178.5 (2)	C6—C5—C4—C3	2.5 (4)
C4—C5—C6—C7	−3.3 (4)	S2—C5—C4—C3	−177.3 (2)
S2—C5—C6—C7	176.5 (2)	C13—C14—N4—C16	171.6 (3)
C4—C5—C6—S1	177.24 (19)	C13—C14—N4—C15	−66.0 (3)
S2—C5—C6—S1	−3.0 (3)	C12—N3—C10—C9	65.4 (3)
C9—S1—C6—C7	7.6 (3)	C11—N3—C10—C9	−171.0 (3)
C9—S1—C6—C5	−172.9 (2)	N3—C10—C9—S1	53.2 (3)
C6—C7—C8—C1	−178.5 (3)	C6—S1—C9—C10	165.6 (2)
C4—C3—C8—C7	−0.9 (4)	N4—C14—C13—S2	−175.0 (2)
C2—C3—C8—C7	179.1 (2)	C5—S2—C13—C14	−179.3 (2)
C4—C3—C8—C1	177.6 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···N1^i	0.96	2.83	3.768 (5)	166
C12—H12C···N1^ii	0.96	2.86	3.731 (5)	152
C7—H7···N3^iii	0.93	2.83	3.737 (3)	165
C13—H13A···N2^iv	0.97	2.69	3.597 (4)	155
C15—H15B···N2^iv	0.96	2.84	3.779 (5)	166
C10—H10B···N1^v	0.97	2.90	3.789 (5)	154
C13—H13B···N4^vi	0.97	2.89	3.738 (4)	147
C16—H16B···N2^vii	0.96	2.99	3.899 (5)	159
C11—H11C···Cg1^viii	0.96	2.90	3.738 (4)	147

Symmetry codes: (i) x+1, −y+3/2, z+1/2; (ii) x+1/2, −y+3/2, −z+1; (iii) x−1/2, y, −z+3/2; (iv) −x, −y+1, −z+1; (v) x+1/2, y, −z+3/2; (vi) −x+1, −y+1, −z+1; (vii) −x+1/2, −y+1, z+1/2; (viii) x, −y+1/2, z+1/2.