trans-2,2′-[(2-Butene-1,4-di­yl)dithio]bis­(4,5-dihydro-1,3-thia­zine)

The title compound, C₁₂H₁₈N₂S₄, was synthesized by the reaction of trans-1,4-dibromo-2-butene and 1,3-thia­zine-2-thione. The mol­ecule contains a centre of inversion at the mid-point of the central double bond and the thia­zine rings have an envelope conformation.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.050
• wR factor = 0.144
• Data-to-parameter ratio = 19.0

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.726     0.910
            Tmin(prime) and Tmax expected:      0.852     0.908
            RR(prime) =      0.850
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.85
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.01
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         S1
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C2
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C4
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.06
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   9 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
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

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

trans-2,2'-[(2-Butene-1,4-diyl)dithio]bis(4,5-dihydro-1,3-thiazine)

Crystal data

C12H18N2S4	F(000) = 336
Mr = 318.52	Dx = 1.374 Mg m^−3
Monoclinic, P21/n	Melting point: 357 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 8.282 (5) Å	Cell parameters from 1520 reflections
b = 10.578 (6) Å	θ = 3.0–26.0°
c = 9.625 (6) Å	µ = 0.60 mm^−1
β = 114.100 (8)°	T = 294 K
V = 769.7 (8) Å^3	Block, colourless
Z = 2	0.26 × 0.20 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer	1567 independent reflections
Radiation source: fine-focus sealed tube	1102 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
φ and ω scans	θmax = 26.4°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→10
Tmin = 0.726, Tmax = 0.910	k = −7→13
4202 measured reflections	l = −11→12

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.144	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0586P)^2 + 0.568P] where P = (Fo^2 + 2Fc^2)/3
1567 reflections	(Δ/σ)max = 0.001
82 parameters	Δρmax = 0.97 e Å^−3
0 restraints	Δρmin = −0.48 e Å^−3

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

	x	y	z	Uiso*/Ueq
S1	0.69683 (13)	0.41117 (10)	0.41364 (13)	0.0713 (4)
S2	0.38467 (11)	0.36247 (8)	0.14298 (11)	0.0526 (3)
N1	0.4859 (4)	0.5980 (3)	0.2323 (3)	0.0493 (7)
C1	0.7903 (5)	0.5460 (4)	0.5323 (4)	0.0609 (10)
H1A	0.7285	0.5601	0.5975	0.073*
H1B	0.9135	0.5293	0.5969	0.073*
C2	0.7778 (7)	0.6600 (5)	0.4415 (5)	0.0859 (15)
H2A	0.8506	0.6476	0.3852	0.103*
H2B	0.8280	0.7301	0.5108	0.103*
C3	0.5978 (5)	0.6964 (4)	0.3323 (5)	0.0668 (11)
H3A	0.5358	0.7314	0.3900	0.080*
H3B	0.6096	0.7637	0.2686	0.080*
C4	0.5198 (4)	0.4831 (3)	0.2605 (3)	0.0392 (7)
C5	0.2224 (4)	0.4546 (3)	−0.0102 (4)	0.0482 (8)
H5A	0.2834	0.5204	−0.0401	0.058*
H5B	0.1645	0.3999	−0.0975	0.058*
C6	0.0848 (4)	0.5143 (3)	0.0315 (3)	0.0423 (7)
H6	0.1214	0.5757	0.1072	0.051*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0539 (6)	0.0510 (6)	0.0752 (7)	0.0060 (5)	−0.0080 (5)	0.0096 (5)
S2	0.0453 (5)	0.0386 (5)	0.0609 (6)	0.0024 (4)	0.0084 (4)	−0.0093 (4)
N1	0.0444 (15)	0.0390 (15)	0.0498 (16)	0.0011 (12)	0.0043 (13)	0.0010 (12)
C1	0.047 (2)	0.079 (3)	0.0443 (19)	0.0019 (19)	0.0060 (16)	−0.0029 (19)
C2	0.084 (3)	0.065 (3)	0.074 (3)	−0.021 (2)	−0.003 (2)	−0.008 (2)
C3	0.069 (2)	0.041 (2)	0.066 (2)	−0.0096 (18)	0.0021 (19)	−0.0044 (18)
C4	0.0328 (15)	0.0423 (17)	0.0396 (16)	0.0024 (13)	0.0119 (13)	−0.0014 (13)
C5	0.0443 (18)	0.053 (2)	0.0400 (17)	−0.0015 (15)	0.0094 (14)	−0.0040 (15)
C6	0.0420 (15)	0.0389 (17)	0.0377 (16)	−0.0004 (14)	0.0078 (13)	−0.0013 (13)

Geometric parameters (Å, º)

S1—C4	1.771 (3)	C2—H2A	0.9700
S1—C1	1.793 (4)	C2—H2B	0.9700
S2—C4	1.768 (3)	C3—H3A	0.9700
S2—C5	1.819 (3)	C3—H3B	0.9700
N1—C4	1.252 (4)	C5—C6	1.494 (5)
N1—C3	1.463 (4)	C5—H5A	0.9700
C1—C2	1.468 (6)	C5—H5B	0.9700
C1—H1A	0.9700	C6—C6^i	1.318 (6)
C1—H1B	0.9700	C6—H6	0.9300
C2—C3	1.482 (6)
C4—S1—C1	100.59 (17)	C2—C3—H3A	107.9
C4—S2—C5	101.36 (16)	N1—C3—H3B	107.9
C4—N1—C3	121.5 (3)	C2—C3—H3B	107.9
C2—C1—S1	111.5 (3)	H3A—C3—H3B	107.2
C2—C1—H1A	109.3	N1—C4—S2	122.3 (2)
S1—C1—H1A	109.3	N1—C4—S1	129.3 (3)
C2—C1—H1B	109.3	S1—C4—S2	108.36 (18)
S1—C1—H1B	109.3	C6—C5—S2	113.6 (2)
H1A—C1—H1B	108.0	C6—C5—H5A	108.8
C1—C2—C3	116.2 (4)	S2—C5—H5A	108.8
C1—C2—H2A	108.2	C6—C5—H5B	108.8
C3—C2—H2A	108.2	S2—C5—H5B	108.8
C1—C2—H2B	108.2	H5A—C5—H5B	107.7
C3—C2—H2B	108.2	C6^i—C6—C5	124.5 (4)
H2A—C2—H2B	107.4	C6^i—C6—H6	117.8
N1—C3—C2	117.7 (3)	C5—C6—H6	117.8
N1—C3—H3A	107.9
C4—S1—C1—C2	−35.0 (4)	C5—S2—C4—N1	3.7 (3)
S1—C1—C2—C3	57.0 (5)	C5—S2—C4—S1	−176.68 (17)
C4—N1—C3—C2	17.3 (6)	C1—S1—C4—N1	9.4 (4)
C1—C2—C3—N1	−48.5 (6)	C1—S1—C4—S2	−170.19 (18)
C3—N1—C4—S2	179.0 (3)	C4—S2—C5—C6	−77.0 (3)
C3—N1—C4—S1	−0.6 (5)	S2—C5—C6—C6^i	−115.0 (4)

Symmetry code: (i) −x, −y+1, −z.