5,5′-Dithio­bis(1-phenyl-1H-tetra­zole)

Brito, I.; Cárdenas, A.; Mundaca, A.; Villalobos, H.; López-Rodríguez, M.

doi:10.1107/S1600536807017291

5,5′-Dithiobis(1-phenyl-1H-tetrazole)

I. Brito, A. Cárdenas, A. Mundaca, H. Villalobos and M. López-Rodríguez

The structure of the title compound, C₁₄H₁₀N₈S₂, comprises two 1-phenyl-1H-tetrazole-5-thiolate units linked by an S—S disulfide bridge. The C—S—S—C torsion angle is 81.9 (1)°. C—H

N hydrogen bonding, with C

N = 3.413 (4) Å and C—H

N = 147°, link the molecules into supramolecular chains in the crystal structure.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807017291/xu2237sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807017291/xu2237Isup2.hkl Contains datablock I

CCDC reference: 648238

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.004 Å
R factor = 0.054
wR factor = 0.149
Data-to-parameter ratio = 16.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT331_ALERT_2_B Small Average Phenyl C-C Dist.   C9     -C14           1.36 Ang.

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.96
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          3
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C11    -   C12     ..       6.35 su
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist.   C2     -C7            1.37 Ang.

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   4 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
   3 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999).

5,5'-Dithiobis(1-phenyl-1H-tetrazole) top

Crystal data top

C₁₄H₁₀N₈S₂	Z = 2
M_r = 354.42	F(000) = 364
Triclinic, P1	D_x = 1.57 Mg m⁻³
Hall symbol: -P 1	Melting point: 418 K
a = 7.241 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.2360 (14) Å	Cell parameters from 2125 reflections
c = 11.7760 (19) Å	θ = 2.6–28.5°
α = 80.97 (2)°	µ = 0.37 mm⁻¹
β = 89.382 (10)°	T = 298 K
γ = 74.66 (3)°	Block, yellow
V = 749.7 (2) Å³	0.42 × 0.23 × 0.12 mm

Data collection top

Nonius KappaCCD area-detector diffractometer	3524 independent reflections
Radiation source: fine-focus sealed tube	2979 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.055
φ and ω scans with κ offsets	θ_max = 28.5°, θ_min = 2.7°
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	h = −9→9
T_min = 0.900, T_max = 0.952	k = −12→12
6734 measured reflections	l = −15→12

Refinement top

Refinement on F²	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ²(F_o²) + (0.0657P)² + 0.2582P] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.054	(Δ/σ)_max = 0.006
wR(F²) = 0.149	Δρ_max = 0.26 e Å⁻³
S = 1.11	Δρ_min = −0.28 e Å⁻³
3524 reflections	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
219 parameters	Extinction coefficient: 0.097 (14)
0 restraints

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.10061 (9)	0.05560 (7)	0.27764 (6)	0.0519 (2)
S2	0.25784 (8)	0.17256 (6)	0.17854 (5)	0.0443 (2)
N1	0.2192 (3)	0.1602 (2)	0.46156 (16)	0.0442 (4)
N2	0.2908 (3)	0.1022 (3)	0.56861 (18)	0.0631 (6)
N3	0.3020 (4)	−0.0401 (3)	0.5830 (2)	0.0711 (7)
N4	0.2430 (3)	−0.0787 (3)	0.4878 (2)	0.0610 (6)
N5	0.6290 (3)	0.0660 (2)	0.12826 (15)	0.0424 (4)
N6	0.7588 (3)	−0.0661 (3)	0.1192 (2)	0.0633 (6)
N7	0.6735 (4)	−0.1700 (3)	0.1474 (2)	0.0692 (7)
N8	0.4901 (3)	−0.1128 (2)	0.1749 (2)	0.0584 (6)
C1	0.1936 (3)	0.0463 (3)	0.4135 (2)	0.0436 (5)
C2	0.1879 (3)	0.3178 (3)	0.41827 (18)	0.0444 (5)
C3	0.3356 (4)	0.3828 (3)	0.4228 (2)	0.0561 (6)
H3	0.455	0.326	0.4542	0.076 (3)*
C4	0.3029 (5)	0.5348 (4)	0.3795 (3)	0.0721 (8)
H4	0.4012	0.582	0.3815	0.076 (3)*
C5	0.1275 (6)	0.6166 (3)	0.3338 (3)	0.0748 (9)
H5	0.1072	0.7192	0.3042	0.076 (3)*
C6	−0.0183 (5)	0.5497 (3)	0.3310 (2)	0.0674 (8)
H6	−0.1375	0.6067	0.2996	0.076 (3)*
C7	0.0101 (4)	0.3991 (3)	0.3742 (2)	0.0541 (6)
H7	−0.0893	0.3528	0.3737	0.076 (3)*
C8	0.4666 (3)	0.0330 (2)	0.16235 (18)	0.0404 (5)
C9	0.6755 (3)	0.2076 (3)	0.10020 (18)	0.0408 (5)
C10	0.7789 (4)	0.2329 (4)	0.0049 (2)	0.0621 (7)
H10	0.8195	0.1588	−0.0417	0.076 (3)*
C11	0.8213 (5)	0.3701 (5)	−0.0201 (3)	0.0778 (10)
H11	0.8933	0.3887	−0.084	0.076 (3)*
C12	0.7603 (4)	0.4788 (4)	0.0463 (3)	0.0654 (8)
H12	0.788	0.5723	0.0276	0.076 (3)*
C13	0.6587 (4)	0.4510 (3)	0.1404 (2)	0.0548 (6)
H13	0.616	0.526	0.186	0.076 (3)*
C14	0.6180 (3)	0.3134 (3)	0.1693 (2)	0.0453 (5)
H14	0.5518	0.2934	0.2355	0.076 (3)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0487 (4)	0.0489 (4)	0.0634 (4)	−0.0252 (3)	−0.0039 (3)	−0.0039 (3)
S2	0.0491 (3)	0.0334 (3)	0.0448 (3)	−0.0060 (2)	0.0010 (2)	0.0016 (2)
N1	0.0426 (9)	0.0468 (11)	0.0348 (9)	−0.0022 (8)	0.0015 (7)	0.0023 (8)
N2	0.0622 (13)	0.0738 (16)	0.0370 (11)	0.0028 (11)	0.0031 (9)	0.0037 (10)
N3	0.0652 (14)	0.0710 (16)	0.0534 (14)	0.0034 (12)	0.0066 (11)	0.0235 (12)
N4	0.0523 (12)	0.0477 (12)	0.0700 (15)	−0.0067 (9)	0.0113 (10)	0.0179 (11)
N5	0.0455 (10)	0.0382 (9)	0.0394 (9)	−0.0001 (8)	−0.0028 (7)	−0.0127 (7)
N6	0.0609 (13)	0.0513 (13)	0.0685 (15)	0.0095 (11)	−0.0040 (11)	−0.0238 (11)
N7	0.0794 (16)	0.0397 (12)	0.0809 (17)	0.0046 (11)	−0.0119 (13)	−0.0212 (11)
N8	0.0745 (15)	0.0340 (10)	0.0655 (14)	−0.0100 (10)	−0.0135 (11)	−0.0113 (9)
C1	0.0349 (10)	0.0392 (11)	0.0516 (12)	−0.0089 (8)	0.0064 (9)	0.0054 (9)
C2	0.0528 (12)	0.0420 (12)	0.0349 (10)	−0.0047 (10)	0.0020 (9)	−0.0096 (9)
C3	0.0615 (15)	0.0548 (15)	0.0541 (14)	−0.0118 (12)	0.0029 (11)	−0.0215 (12)
C4	0.096 (2)	0.0628 (18)	0.0705 (19)	−0.0329 (17)	0.0110 (17)	−0.0307 (15)
C5	0.130 (3)	0.0374 (14)	0.0544 (16)	−0.0145 (16)	−0.0020 (17)	−0.0131 (12)
C6	0.092 (2)	0.0422 (14)	0.0552 (15)	0.0058 (14)	−0.0190 (14)	−0.0095 (12)
C7	0.0601 (14)	0.0471 (14)	0.0488 (13)	−0.0011 (11)	−0.0084 (11)	−0.0105 (11)
C8	0.0504 (12)	0.0330 (10)	0.0356 (10)	−0.0059 (9)	−0.0057 (8)	−0.0072 (8)
C9	0.0372 (10)	0.0471 (12)	0.0362 (10)	−0.0080 (9)	−0.0039 (8)	−0.0061 (9)
C10	0.0502 (14)	0.098 (2)	0.0456 (14)	−0.0258 (14)	0.0070 (10)	−0.0230 (14)
C11	0.0707 (18)	0.130 (3)	0.0471 (15)	−0.061 (2)	0.0058 (13)	0.0026 (17)
C12	0.0666 (17)	0.0761 (19)	0.0596 (16)	−0.0424 (15)	−0.0123 (13)	0.0122 (14)
C13	0.0532 (14)	0.0484 (14)	0.0639 (16)	−0.0184 (11)	−0.0075 (11)	−0.0037 (11)
C14	0.0487 (12)	0.0445 (12)	0.0441 (12)	−0.0152 (10)	0.0040 (9)	−0.0070 (9)

Geometric parameters (Å, º) top

S1—S2	2.0128 (9)	C4—C5	1.361 (5)
S1—C1	1.724 (3)	C4—H4	0.93
S2—C8	1.739 (2)	C5—C6	1.360 (5)
N1—C1	1.324 (3)	C5—H5	0.93
N1—N2	1.342 (3)	C6—C7	1.366 (4)
N1—C2	1.423 (3)	C6—H6	0.93
N2—N3	1.280 (4)	C7—H7	0.93
N3—N4	1.336 (4)	C9—C14	1.349 (3)
N4—C1	1.302 (3)	C9—C10	1.366 (3)
N5—C8	1.333 (3)	C10—C11	1.369 (5)
N5—N6	1.347 (3)	C10—H10	0.93
N5—C9	1.424 (3)	C11—C12	1.349 (5)
N6—N7	1.274 (4)	C11—H11	0.93
N7—N8	1.349 (3)	C12—C13	1.352 (4)
N8—C8	1.296 (3)	C12—H12	0.93
C2—C3	1.363 (4)	C13—C14	1.370 (3)
C2—C7	1.368 (3)	C13—H13	0.93
C3—C4	1.375 (4)	C14—H14	0.93
C3—H3	0.93

C1—S1—S2	102.13 (8)	C4—C5—H5	119.7
C8—S2—S1	102.83 (8)	C5—C6—C7	120.1 (3)
C1—N1—N2	107.4 (2)	C5—C6—H6	119.9
C1—N1—C2	131.64 (19)	C7—C6—H6	119.9
N2—N1—C2	121.0 (2)	C6—C7—C2	118.6 (3)
N3—N2—N1	106.8 (2)	C6—C7—H7	120.7
N2—N3—N4	110.7 (2)	C2—C7—H7	120.7
C1—N4—N3	106.0 (2)	N8—C8—N5	109.6 (2)
C8—N5—N6	107.5 (2)	N8—C8—S2	127.8 (2)
C8—N5—C9	131.47 (18)	N5—C8—S2	122.48 (16)
N6—N5—C9	121.0 (2)	C14—C9—C10	121.3 (2)
N7—N6—N5	105.9 (2)	C14—C9—N5	119.1 (2)
N6—N7—N8	112.0 (2)	C10—C9—N5	119.6 (2)
C8—N8—N7	105.0 (2)	C9—C10—C11	118.3 (3)
N4—C1—N1	109.1 (2)	C9—C10—H10	120.8
N4—C1—S1	123.4 (2)	C11—C10—H10	120.8
N1—C1—S1	127.41 (17)	C12—C11—C10	121.1 (3)
C3—C2—C7	122.2 (2)	C12—C11—H11	119.5
C3—C2—N1	118.9 (2)	C10—C11—H11	119.5
C7—C2—N1	118.8 (2)	C11—C12—C13	119.5 (3)
C2—C3—C4	118.0 (3)	C11—C12—H12	120.2
C2—C3—H3	121	C13—C12—H12	120.2
C4—C3—H3	121	C12—C13—C14	120.8 (3)
C5—C4—C3	120.4 (3)	C12—C13—H13	119.6
C5—C4—H4	119.8	C14—C13—H13	119.6
C3—C4—H4	119.8	C9—C14—C13	118.9 (2)
C6—C5—C4	120.6 (3)	C9—C14—H14	120.5
C6—C5—H5	119.7	C13—C14—H14	120.5

C1—S1—S2—C8	81.90 (11)	C4—C5—C6—C7	0.0 (5)
C1—N1—N2—N3	−1.5 (3)	C5—C6—C7—C2	−1.0 (4)
C2—N1—N2—N3	179.7 (2)	C3—C2—C7—C6	1.5 (4)
N1—N2—N3—N4	1.1 (3)	N1—C2—C7—C6	−178.9 (2)
N2—N3—N4—C1	−0.3 (3)	N7—N8—C8—N5	0.0 (3)
C8—N5—N6—N7	−0.2 (3)	N7—N8—C8—S2	176.95 (18)
C9—N5—N6—N7	−178.5 (2)	N6—N5—C8—N8	0.1 (2)
N5—N6—N7—N8	0.2 (3)	C9—N5—C8—N8	178.2 (2)
N6—N7—N8—C8	−0.1 (3)	N6—N5—C8—S2	−177.03 (16)
N3—N4—C1—N1	−0.6 (3)	C9—N5—C8—S2	1.1 (3)
N3—N4—C1—S1	−178.04 (17)	S1—S2—C8—N8	21.3 (2)
N2—N1—C1—N4	1.3 (2)	S1—S2—C8—N5	−162.12 (16)
C2—N1—C1—N4	179.9 (2)	C8—N5—C9—C14	44.7 (3)
N2—N1—C1—S1	178.59 (16)	N6—N5—C9—C14	−137.4 (2)
C2—N1—C1—S1	−2.8 (3)	C8—N5—C9—C10	−136.0 (2)
S2—S1—C1—N4	−132.17 (18)	N6—N5—C9—C10	41.9 (3)
S2—S1—C1—N1	50.9 (2)	C14—C9—C10—C11	−0.9 (4)
C1—N1—C2—C3	−124.9 (3)	N5—C9—C10—C11	179.9 (2)
N2—N1—C2—C3	53.5 (3)	C9—C10—C11—C12	−1.0 (4)
C1—N1—C2—C7	55.5 (3)	C10—C11—C12—C13	1.2 (5)
N2—N1—C2—C7	−126.0 (2)	C11—C12—C13—C14	0.4 (4)
C7—C2—C3—C4	−1.1 (4)	C10—C9—C14—C13	2.4 (4)
N1—C2—C3—C4	179.4 (2)	N5—C9—C14—C13	−178.3 (2)
C2—C3—C4—C5	0.0 (4)	C12—C13—C14—C9	−2.2 (4)
C3—C4—C5—C6	0.5 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···N7ⁱ	0.93	2.60	3.413 (4)	147
C14—H14···S2	0.93	2.78	3.202 (2)	108

Symmetry code: (i) x−1, y+1, z.

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

5,5′-Dithio­bis(1-phenyl-1H-tetra­zole)

Supporting information

Key indicators

checkCIF/PLATON results

5,5′-Dithiobis(1-phenyl-1H-tetrazole)