1,6-Bis(1-phenyl-1H-tetrazol-5-yl­sulfanyl)­hexane

The title compound, C₂₀H₂₂N₈S₂, has a center of inversion at the mid-point of the central C—C bond, and all C—C σ bonds in the hexa­methyl­ene group adopt the normal anti staggered conformation. The two tetrazolyl rings are parallel to each other. The dihedral angle between the phenyl ring and the attached tetrazolyl ring is 41.8 (3)°.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.049
• wR factor = 0.110
• Data-to-parameter ratio = 15.9

checkCIF/PLATON results

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Alert level C
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?

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

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

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Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); 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.

1,6-Bis(1-phenyl-1H-tetrazol-5-ylsulfanyl)hexane

Crystal data

C20H22N8S2	F(000) = 460
Mr = 438.58	Dx = 1.381 Mg m^−3
Monoclinic, P21/c	Melting point: 432–433 K K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.467 (3) Å	Cell parameters from 594 reflections
b = 16.753 (6) Å	θ = 2.8–22.9°
c = 8.606 (3) Å	µ = 0.28 mm^−1
β = 101.587 (7)°	T = 293 K
V = 1054.7 (6) Å^3	Block, colorless
Z = 2	0.26 × 0.16 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer	2160 independent reflections
Radiation source: fine-focus sealed tube	1305 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
φ and ω scans	θmax = 26.4°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −6→9
Tmin = 0.935, Tmax = 0.967	k = −20→19
6037 measured reflections	l = −10→8

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.050	w = 1/[σ^2(Fo^2) + (0.0495P)^2 + 0.0623P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.110	(Δ/σ)max = 0.001
S = 1.00	Δρmax = 0.21 e Å^−3
2160 reflections	Δρmin = −0.26 e Å^−3
136 parameters

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	0.08429 (9)	0.72180 (4)	−0.04977 (9)	0.0542 (3)
N1	0.4253 (3)	0.66771 (11)	0.0816 (2)	0.0395 (5)
N2	0.4226 (3)	0.79034 (12)	0.0002 (3)	0.0574 (6)
N3	0.5963 (3)	0.76709 (14)	0.0664 (3)	0.0666 (7)
N4	0.6009 (3)	0.69470 (13)	0.1156 (3)	0.0565 (6)
C1	0.3846 (3)	0.58713 (13)	0.1158 (3)	0.0362 (6)
C2	0.4712 (3)	0.55395 (15)	0.2570 (3)	0.0463 (7)
H2	0.5499	0.5842	0.3317	0.056*
C3	0.4388 (4)	0.47447 (16)	0.2857 (3)	0.0542 (7)
H3	0.4986	0.4509	0.3797	0.065*
C4	0.3200 (4)	0.43030 (15)	0.1777 (3)	0.0522 (7)
H4	0.2987	0.3770	0.1984	0.063*
C5	0.2323 (3)	0.46478 (14)	0.0387 (3)	0.0490 (7)
H5	0.1496	0.4350	−0.0338	0.059*
C6	0.2657 (3)	0.54314 (13)	0.0058 (3)	0.0430 (6)
H6	0.2085	0.5661	−0.0898	0.052*
C7	0.3187 (3)	0.72793 (14)	0.0109 (3)	0.0405 (6)
C8	0.0337 (4)	0.82298 (14)	−0.1190 (3)	0.0500 (7)
H8A	0.1225	0.8387	−0.1815	0.060*
H8B	−0.0857	0.8234	−0.1887	0.060*
C9	0.0347 (3)	0.88453 (14)	0.0091 (3)	0.0459 (6)
H9A	0.1526	0.8839	0.0813	0.055*
H9B	−0.0580	0.8711	0.0692	0.055*
C10	−0.0019 (3)	0.96732 (14)	−0.0605 (3)	0.0452 (7)
H10A	0.0888	0.9792	−0.1236	0.054*
H10B	−0.1207	0.9674	−0.1312	0.054*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0437 (4)	0.0301 (3)	0.0824 (6)	0.0001 (3)	−0.0027 (3)	0.0050 (3)
N1	0.0371 (11)	0.0306 (11)	0.0494 (13)	0.0000 (9)	0.0049 (9)	−0.0040 (9)
N2	0.0511 (15)	0.0345 (13)	0.0853 (18)	−0.0064 (10)	0.0106 (12)	0.0006 (11)
N3	0.0463 (15)	0.0410 (15)	0.111 (2)	−0.0096 (11)	0.0112 (14)	−0.0111 (14)
N4	0.0390 (13)	0.0423 (13)	0.0849 (18)	−0.0021 (10)	0.0047 (11)	−0.0120 (12)
C1	0.0399 (13)	0.0269 (12)	0.0428 (14)	0.0055 (10)	0.0110 (11)	−0.0008 (10)
C2	0.0509 (16)	0.0430 (15)	0.0430 (15)	0.0096 (12)	0.0046 (12)	−0.0048 (12)
C3	0.0697 (19)	0.0505 (17)	0.0448 (17)	0.0189 (14)	0.0172 (15)	0.0117 (13)
C4	0.0662 (19)	0.0313 (14)	0.0644 (18)	0.0070 (13)	0.0258 (15)	0.0065 (14)
C5	0.0523 (16)	0.0336 (14)	0.0613 (18)	−0.0018 (12)	0.0118 (14)	−0.0065 (13)
C6	0.0487 (15)	0.0314 (13)	0.0472 (16)	0.0056 (11)	0.0057 (12)	0.0011 (11)
C7	0.0448 (15)	0.0281 (13)	0.0477 (16)	−0.0002 (11)	0.0073 (12)	−0.0032 (11)
C8	0.0503 (16)	0.0347 (15)	0.0589 (17)	0.0077 (12)	−0.0037 (13)	0.0053 (13)
C9	0.0492 (15)	0.0337 (15)	0.0556 (17)	0.0079 (11)	0.0126 (12)	0.0077 (12)
C10	0.0423 (15)	0.0379 (15)	0.0555 (18)	0.0050 (12)	0.0101 (13)	0.0062 (11)

Geometric parameters (Å, º)

S1—C7	1.726 (2)	C4—C5	1.370 (3)
S1—C8	1.811 (2)	C4—H4	0.9300
N1—C7	1.352 (3)	C5—C6	1.377 (3)
N1—N4	1.362 (3)	C5—H5	0.9300
N1—C1	1.428 (3)	C6—H6	0.9300
N2—C7	1.316 (3)	C8—C9	1.508 (3)
N2—N3	1.365 (3)	C8—H8A	0.9700
N3—N4	1.283 (3)	C8—H8B	0.9700
C1—C2	1.374 (3)	C9—C10	1.514 (3)
C1—C6	1.375 (3)	C9—H9A	0.9700
C2—C3	1.384 (3)	C9—H9B	0.9700
C2—H2	0.9300	C10—C10^i	1.507 (5)
C3—C4	1.366 (3)	C10—H10A	0.9700
C3—H3	0.9300	C10—H10B	0.9700
C7—S1—C8	100.10 (12)	C1—C6—H6	120.4
C7—N1—N4	107.65 (19)	C5—C6—H6	120.4
C7—N1—C1	131.92 (19)	N2—C7—N1	108.8 (2)
N4—N1—C1	120.37 (19)	N2—C7—S1	127.02 (19)
C7—N2—N3	105.5 (2)	N1—C7—S1	124.14 (18)
N4—N3—N2	111.6 (2)	C9—C8—S1	115.43 (18)
N3—N4—N1	106.40 (19)	C9—C8—H8A	108.4
C2—C1—C6	121.1 (2)	S1—C8—H8A	108.4
C2—C1—N1	118.9 (2)	C9—C8—H8B	108.4
C6—C1—N1	120.0 (2)	S1—C8—H8B	108.4
C1—C2—C3	118.6 (2)	H8A—C8—H8B	107.5
C1—C2—H2	120.7	C8—C9—C10	111.3 (2)
C3—C2—H2	120.7	C8—C9—H9A	109.4
C4—C3—C2	120.8 (2)	C10—C9—H9A	109.4
C4—C3—H3	119.6	C8—C9—H9B	109.4
C2—C3—H3	119.6	C10—C9—H9B	109.4
C3—C4—C5	119.8 (2)	H9A—C9—H9B	108.0
C3—C4—H4	120.1	C10^i—C10—C9	114.5 (2)
C5—C4—H4	120.1	C10^i—C10—H10A	108.6
C4—C5—C6	120.5 (2)	C9—C10—H10A	108.6
C4—C5—H5	119.8	C10^i—C10—H10B	108.6
C6—C5—H5	119.8	C9—C10—H10B	108.6
C1—C6—C5	119.2 (2)	H10A—C10—H10B	107.6
C7—N2—N3—N4	−0.1 (3)	N1—C1—C6—C5	178.0 (2)
N2—N3—N4—N1	0.2 (3)	C4—C5—C6—C1	−1.7 (4)
C7—N1—N4—N3	−0.2 (3)	N3—N2—C7—N1	0.0 (3)
C1—N1—N4—N3	177.4 (2)	N3—N2—C7—S1	178.65 (19)
C7—N1—C1—C2	−141.1 (3)	N4—N1—C7—N2	0.2 (3)
N4—N1—C1—C2	42.0 (3)	C1—N1—C7—N2	−177.0 (2)
C7—N1—C1—C6	41.3 (4)	N4—N1—C7—S1	−178.59 (17)
N4—N1—C1—C6	−135.6 (2)	C1—N1—C7—S1	4.2 (4)
C6—C1—C2—C3	1.1 (4)	C8—S1—C7—N2	−2.2 (3)
N1—C1—C2—C3	−176.5 (2)	C8—S1—C7—N1	176.3 (2)
C1—C2—C3—C4	−1.5 (4)	C7—S1—C8—C9	−77.5 (2)
C2—C3—C4—C5	0.3 (4)	S1—C8—C9—C10	177.85 (18)
C3—C4—C5—C6	1.3 (4)	C8—C9—C10—C10^i	−178.5 (3)
C2—C1—C6—C5	0.5 (4)

Symmetry code: (i) −x, −y+2, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···N4^ii	0.97	2.61	3.576 (3)	173

Symmetry code: (ii) x−1, −y+3/2, z−1/2.