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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)°.
Supporting information
CCDC reference: 255885
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.049
- wR factor = 0.110
- Data-to-parameter ratio = 15.9
checkCIF/PLATON results
No syntax errors found
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
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-1
H-tetrazol-5-ylsulfanyl)hexane
top
Crystal data top
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) Å3 | Block, colorless |
Z = 2 | 0.26 × 0.16 × 0.12 mm |
Data collection top
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 top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.050 | w = 1/[σ2(Fo2) + (0.0495P)2 + 0.0623P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 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 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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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—C10i | 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 | C10i—C10—C9 | 114.5 (2) |
C5—C4—H4 | 120.1 | C10i—C10—H10A | 108.6 |
C4—C5—C6 | 120.5 (2) | C9—C10—H10A | 108.6 |
C4—C5—H5 | 119.8 | C10i—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—C10i | −178.5 (3) |
C2—C1—C6—C5 | 0.5 (4) | | |
Symmetry code: (i) −x, −y+2, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8B···N4ii | 0.97 | 2.61 | 3.576 (3) | 173 |
Symmetry code: (ii) x−1, −y+3/2, z−1/2. |
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