1,2-Bis(1,3-dithio­lan-2-ylidene)hydrazine

The title molecule, C₆H₈N₂S₄, possesses a crystallographically imposed center of symmetry. The two five-membered rings are in half-chair conformations. The crystal packing is stabilized mainly by van der Waals forces.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.046
• wR factor = 0.130
• Data-to-parameter ratio = 17.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT048_ALERT_1_C MoietyFormula Not Given ........................          ?
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.82
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.88
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature         293
PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature ....        293
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.816
            Tmax scaled      0.816 Tmin scaled      0.708

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: Bruker SMART (Bruker, 1998); cell refinement: Bruker SMART; data reduction: Bruker SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Bruker SHELXTL (Bruker, 1999); software used to prepare material for publication: Bruker SHELXTL.

1,2-Bis(1,3-dithiolan-2-ylidene)hydrazine

Crystal data

C6H8N2S4	F(000) = 244
Mr = 236.38	Dx = 1.619 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.300 (2) Å	Cell parameters from 1494 reflections
b = 7.737 (2) Å	θ = 2.6–26.4°
c = 10.386 (3) Å	µ = 0.92 mm^−1
β = 106.712 (4)°	T = 293 K
V = 484.9 (2) Å^3	Prism, colorless
Z = 2	0.30 × 0.28 × 0.22 mm

Data collection

CCD area detector diffractometer	992 independent reflections
Radiation source: fine-focus sealed tube	834 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
phi and ω scans	θmax = 26.4°, θmin = 3.3°
Absorption correction: multi-scan SADABS (Sheldrick, 1996)	h = −7→7
Tmin = 0.867, Tmax = 1.000	k = −9→9
2712 measured reflections	l = −12→8

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.046	H-atom parameters constrained
wR(F^2) = 0.130	w = 1/[σ^2(Fo^2) + (0.0675P)^2 + 0.6306P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
992 reflections	Δρmax = 1.06 e Å^−3
56 parameters	Δρmin = −0.37 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.161 (16)

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	1.10441 (14)	0.27867 (12)	0.15937 (10)	0.0489 (4)
S2	0.61750 (14)	0.25208 (11)	0.04382 (9)	0.0483 (4)
N1	0.8901 (4)	0.0247 (4)	−0.0092 (3)	0.0449 (7)
C1	0.8784 (5)	0.1649 (4)	0.0550 (3)	0.0363 (7)
C2	0.9419 (6)	0.4598 (4)	0.1896 (4)	0.0506 (8)
H2A	1.0134	0.5113	0.2764	0.061*
H2B	0.9290	0.5473	0.1208	0.061*
C3	0.7157 (5)	0.3936 (4)	0.1865 (3)	0.0459 (8)
H3A	0.6141	0.4897	0.1795	0.055*
H3B	0.7239	0.3312	0.2688	0.055*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0380 (5)	0.0475 (6)	0.0583 (6)	0.0010 (3)	0.0093 (4)	−0.0102 (4)
S2	0.0400 (5)	0.0539 (6)	0.0475 (6)	0.0052 (3)	0.0069 (4)	−0.0102 (3)
N1	0.0362 (14)	0.0474 (15)	0.0490 (15)	0.0021 (11)	0.0089 (11)	−0.0090 (12)
C1	0.0389 (15)	0.0349 (15)	0.0358 (15)	0.0029 (11)	0.0118 (12)	0.0011 (11)
C2	0.0561 (19)	0.0381 (17)	0.056 (2)	0.0005 (14)	0.0138 (15)	−0.0109 (15)
C3	0.0519 (19)	0.0425 (17)	0.0431 (17)	0.0092 (14)	0.0134 (14)	−0.0049 (13)

Geometric parameters (Å, º)

S1—C1	1.757 (3)	C2—C3	1.506 (5)
S1—C2	1.816 (3)	C2—H2A	0.9700
S2—C1	1.749 (3)	C2—H2B	0.9700
S2—C3	1.803 (3)	C3—H3A	0.9700
N1—C1	1.287 (4)	C3—H3B	0.9700
N1—N1^i	1.396 (5)
C1—S1—C2	95.5 (2)	C3—C2—H2B	110.1
C1—S2—C3	94.9 (2)	S1—C2—H2B	110.1
C1—N1—N1^i	111.2 (3)	H2A—C2—H2B	108.4
N1—C1—S2	118.9 (2)	C2—C3—S2	108.8 (2)
N1—C1—S1	125.8 (2)	C2—C3—H3A	109.9
S2—C1—S1	115.3 (2)	S2—C3—H3A	109.9
C3—C2—S1	108.1 (2)	C2—C3—H3B	109.9
C3—C2—H2A	110.1	S2—C3—H3B	109.9
S1—C2—H2A	110.1	H3A—C3—H3B	108.3
N1^i—N1—C1—S2	179.1 (3)	C2—S1—C1—S2	−7.2 (2)
N1^i—N1—C1—S1	−2.6 (5)	C1—S1—C2—C3	31.4 (3)
C3—S2—C1—N1	164.3 (3)	S1—C2—C3—S2	−45.2 (3)
C3—S2—C1—S1	−14.2 (2)	C1—S2—C3—C2	36.0 (3)
C2—S1—C1—N1	174.4 (3)

Symmetry code: (i) −x+2, −y, −z.