2,2'-[1,4-Phenyl­enebis­(methyl­ene­thio)]­di­thia­zole

The title compound, C₁₄H₁₂N₂S₄, crystallizes in the monoclinic space group P2₁/c. The mol­ecule is centrosymmetric; the two thia­zole rings are parallel to each other, while the thia­zole and the benzene planes are almost perpendicular to each other, forming a dihedral angle of 100.6 (2)°.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.040
• wR factor = 0.086
• Data-to-parameter ratio = 16.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



ABSTM_02  Alert C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
          Tmin and Tmax reported:      0.875     1.000
          Tmin' and Tmax expected:      0.881     0.906
          RR' =      0.900
          Please check that your absorption correction is appropriate.

HYDTR_01  Alert C The hydrogen treatment should only be one of the following
          keywords
          *  refall
          *  refxyz
          *  refU
          *  noref
          *  undef
          *  constr
          *  none
          *  mixed
          Hydrogen treatment given as const

General Notes



ABSTM_02  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      0.906
          Tmax scaled      0.906 Tmin scaled      0.792


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 2 Alert Level C = Please check

---

Computing details

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

2,2'-[1,4-phenylenebis(methylenethio)]dithiazole

Crystal data

C14H12N2S4	F(000) = 348
Mr = 336.50	? # Insert any comments here.
Monoclinic, P21/c	Dx = 1.484 Mg m^−3
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 6.366 (3) Å	Cell parameters from 567 reflections
b = 15.411 (6) Å	θ = 2.6–26.2°
c = 7.679 (3) Å	µ = 0.62 mm^−1
β = 91.331 (7)°	T = 293 K
V = 753.2 (5) Å^3	Prism, colourless
Z = 2	0.20 × 0.18 × 0.16 mm

Data collection

Bruker CCD area-detector diffractometer	1518 independent reflections
Radiation source: fine-focus sealed tube	1074 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
φ and ω scans	θmax = 26.4°, θmin = 2.6°
Absorption correction: multi-scan SADABS (Bruker, 1997)	h = −7→7
Tmin = 0.875, Tmax = 1.000	k = −15→19
3479 measured reflections	l = −9→7

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.086	Const
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0327P)^2 + 0.1354P] where P = (Fo^2 + 2Fc^2)/3
1518 reflections	(Δ/σ)max < 0.001
91 parameters	Δρmax = 0.20 e Å^−3
0 restraints	Δρmin = −0.22 e Å^−3

Special details

Experimental. ? #Insert any special details here.

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	0.26130 (10)	0.22553 (4)	0.51522 (9)	0.0484 (2)
S2	0.70899 (11)	0.24959 (4)	0.38669 (10)	0.0528 (2)
N1	0.4669 (3)	0.37404 (13)	0.4779 (3)	0.0532 (6)
C1	0.4746 (4)	0.29021 (16)	0.4611 (3)	0.0394 (6)
C2	0.6565 (5)	0.40912 (18)	0.4280 (4)	0.0604 (8)
H2	0.6810	0.4686	0.4309	0.072*
C3	0.8021 (4)	0.35339 (18)	0.3758 (4)	0.0585 (8)
H3	0.9351	0.3688	0.3388	0.070*
C4	0.3503 (4)	0.11827 (15)	0.4543 (4)	0.0530 (7)
H4A	0.3934	0.1181	0.3340	0.064*
H4B	0.4694	0.1010	0.5275	0.064*
C5	0.1698 (4)	0.05625 (15)	0.4777 (4)	0.0438 (6)
C6	0.1553 (4)	0.00672 (16)	0.6271 (4)	0.0501 (7)
H6	0.2592	0.0109	0.7138	0.060*
C7	0.0126 (4)	0.04910 (16)	0.3511 (4)	0.0494 (7)
H7	0.0198	0.0822	0.2502	0.059*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0384 (4)	0.0437 (4)	0.0636 (5)	0.0005 (3)	0.0091 (3)	−0.0051 (3)
S2	0.0428 (4)	0.0439 (4)	0.0723 (5)	0.0008 (3)	0.0125 (3)	−0.0032 (3)
N1	0.0508 (14)	0.0388 (13)	0.0700 (15)	0.0032 (10)	0.0023 (12)	−0.0025 (11)
C1	0.0371 (14)	0.0398 (14)	0.0412 (14)	0.0025 (10)	−0.0024 (11)	−0.0008 (11)
C2	0.0609 (19)	0.0401 (15)	0.080 (2)	−0.0067 (14)	0.0018 (17)	0.0020 (14)
C3	0.0487 (17)	0.0530 (17)	0.074 (2)	−0.0083 (14)	0.0097 (16)	0.0065 (14)
C4	0.0422 (15)	0.0443 (15)	0.0731 (18)	0.0008 (12)	0.0119 (14)	−0.0075 (14)
C5	0.0385 (14)	0.0328 (13)	0.0606 (17)	0.0011 (10)	0.0107 (14)	−0.0064 (12)
C6	0.0465 (16)	0.0463 (15)	0.0572 (17)	0.0010 (12)	−0.0019 (14)	−0.0041 (13)
C7	0.0536 (18)	0.0421 (14)	0.0528 (16)	0.0011 (12)	0.0081 (15)	0.0021 (12)

Geometric parameters (Å, º)

S1—C1	1.743 (3)	C4—C5	1.509 (3)
S1—C4	1.812 (3)	C4—H4A	0.9700
S2—C3	1.709 (3)	C4—H4B	0.9700
S2—C1	1.727 (2)	C5—C7	1.383 (4)
N1—C1	1.299 (3)	C5—C6	1.383 (4)
N1—C2	1.385 (3)	C6—C7^i	1.385 (4)
C2—C3	1.332 (4)	C6—H6	0.9300
C2—H2	0.9300	C7—C6^i	1.385 (4)
C3—H3	0.9300	C7—H7	0.9300
C1—S1—C4	102.13 (12)	S1—C4—H4A	110.2
C3—S2—C1	88.87 (13)	C5—C4—H4B	110.2
C1—N1—C2	109.0 (2)	S1—C4—H4B	110.2
N1—C1—S2	115.36 (18)	H4A—C4—H4B	108.5
N1—C1—S1	120.89 (19)	C7—C5—C6	118.6 (2)
S2—C1—S1	123.74 (14)	C7—C5—C4	120.5 (2)
C3—C2—N1	116.7 (2)	C6—C5—C4	120.9 (3)
C3—C2—H2	121.7	C5—C6—C7^i	120.6 (3)
N1—C2—H2	121.7	C5—C6—H6	119.7
C2—C3—S2	110.1 (2)	C7^i—C6—H6	119.7
C2—C3—H3	124.9	C5—C7—C6^i	120.8 (2)
S2—C3—H3	124.9	C5—C7—H7	119.6
C5—C4—S1	107.66 (17)	C6^i—C7—H7	119.6
C5—C4—H4A	110.2
C2—N1—C1—S2	0.4 (3)	C1—S2—C3—C2	0.4 (2)
C2—N1—C1—S1	179.33 (19)	C1—S1—C4—C5	−174.31 (19)
C3—S2—C1—N1	−0.5 (2)	S1—C4—C5—C7	81.2 (3)
C3—S2—C1—S1	−179.37 (17)	S1—C4—C5—C6	−97.5 (2)
C4—S1—C1—N1	176.5 (2)	C7—C5—C6—C7^i	0.3 (4)
C4—S1—C1—S2	−4.72 (19)	C4—C5—C6—C7^i	179.0 (2)
C1—N1—C2—C3	−0.1 (4)	C6—C5—C7—C6^i	−0.3 (4)
N1—C2—C3—S2	−0.3 (4)	C4—C5—C7—C6^i	−179.0 (2)

Symmetry code: (i) −x, −y, −z+1.