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In the title compound, C18H18N8OS2, the two 1-phenyl-1H-tetrazole-5-thiol end-groups lie on the same side of the ether chain and are oriented in the same direction. The two phenyl groups attached to the tetrazole rings are almost perpendicular to each other, the dihedral angle being 87.7 (3)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805013784/wn6352sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805013784/wn6352Isup2.hkl
Contains datablock I

CCDC reference: 274663

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.058
  • wR factor = 0.119
  • Data-to-parameter ratio = 15.9

checkCIF/PLATON results

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Alert level C PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
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 0 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 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

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.

2,2'-bis(1-phenyl-1H-tetrazole-5-ylsulfanyl) ether top
Crystal data top
C18H18N8OS2Dx = 1.387 Mg m3
Mr = 426.52Melting point: 417 K
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 900 reflections
a = 7.2873 (15) Åθ = 2.7–22.2°
b = 18.657 (4) ŵ = 0.29 mm1
c = 30.047 (6) ÅT = 293 K
V = 4085.2 (15) Å3Block, colourless
Z = 80.38 × 0.20 × 0.16 mm
F(000) = 1776
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
4175 independent reflections
Radiation source: fine-focus sealed tube2572 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.077
φ and ω scansθmax = 26.4°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 89
Tmin = 0.933, Tmax = 0.955k = 2123
21954 measured reflectionsl = 2737
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0286P)2 + 3.8597P]
where P = (Fo2 + 2Fc2)/3
4175 reflections(Δ/σ)max = 0.001
262 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.27 e Å3
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
xyzUiso*/Ueq
S10.90785 (12)0.22093 (4)0.30420 (3)0.0503 (2)
S20.71485 (13)0.58871 (5)0.42315 (3)0.0603 (3)
O10.8356 (3)0.42540 (10)0.34173 (7)0.0479 (6)
N11.2443 (3)0.15819 (12)0.31221 (8)0.0396 (6)
N21.4254 (4)0.17577 (14)0.31651 (9)0.0509 (7)
N31.4319 (4)0.24523 (15)0.31596 (10)0.0567 (8)
N41.2604 (4)0.27470 (13)0.31138 (9)0.0527 (7)
N51.0712 (4)0.55214 (15)0.44383 (10)0.0577 (8)
N61.1889 (4)0.56413 (17)0.47859 (11)0.0670 (9)
N71.1104 (5)0.60153 (17)0.50930 (10)0.0625 (8)
N80.9355 (4)0.61429 (14)0.49528 (9)0.0502 (7)
C11.1084 (4)0.06214 (16)0.26898 (11)0.0466 (8)
H11.09100.09420.24560.056*
C21.0567 (5)0.00898 (17)0.26475 (13)0.0610 (10)
H21.00160.02490.23870.073*
C31.0871 (5)0.05578 (17)0.29913 (15)0.0628 (11)
H31.05340.10360.29600.075*
C41.1664 (5)0.03303 (19)0.33803 (14)0.0609 (10)
H41.18740.06560.36090.073*
C51.2156 (4)0.03866 (17)0.34354 (11)0.0493 (8)
H51.26660.05490.37010.059*
C61.1861 (4)0.08459 (15)0.30837 (10)0.0378 (7)
C71.1461 (4)0.21938 (15)0.30905 (10)0.0391 (7)
C80.8728 (5)0.31732 (15)0.30187 (10)0.0462 (8)
H8A0.97410.33920.28590.055*
H8B0.76110.32730.28550.055*
C90.8592 (5)0.35030 (15)0.34736 (11)0.0516 (9)
H9A0.75560.33030.36340.062*
H9B0.96990.34070.36420.062*
C100.7970 (5)0.45995 (16)0.38267 (10)0.0522 (9)
H10A0.89340.45000.40400.063*
H10B0.68180.44260.39470.063*
C110.7851 (5)0.53971 (15)0.37396 (10)0.0456 (8)
H11A0.69770.54840.35020.055*
H11B0.90400.55710.36420.055*
C120.9142 (5)0.58380 (17)0.45478 (11)0.0489 (8)
C130.8119 (5)0.65690 (17)0.52156 (10)0.0497 (9)
C140.8792 (6)0.71881 (19)0.54124 (11)0.0633 (10)
H141.00090.73240.53740.076*
C150.7613 (8)0.7600 (2)0.56677 (12)0.0775 (13)
H150.80450.80140.58040.093*
C160.5808 (7)0.7402 (2)0.57209 (12)0.0772 (13)
H160.50250.76830.58920.093*
C170.5158 (6)0.6786 (2)0.55212 (12)0.0710 (12)
H170.39330.66580.55550.085*
C180.6314 (6)0.63600 (19)0.52706 (12)0.0609 (10)
H180.58850.59390.51410.073*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0446 (5)0.0344 (4)0.0719 (6)0.0017 (4)0.0012 (5)0.0046 (4)
S20.0576 (6)0.0653 (6)0.0579 (6)0.0143 (5)0.0060 (5)0.0258 (5)
O10.0675 (16)0.0361 (11)0.0403 (12)0.0065 (11)0.0006 (11)0.0049 (10)
N10.0357 (15)0.0322 (13)0.0508 (16)0.0017 (11)0.0024 (13)0.0023 (12)
N20.0402 (18)0.0491 (16)0.0633 (19)0.0059 (14)0.0023 (15)0.0078 (14)
N30.050 (2)0.0506 (17)0.070 (2)0.0146 (15)0.0034 (16)0.0105 (15)
N40.0553 (19)0.0373 (14)0.0655 (19)0.0082 (14)0.0043 (15)0.0060 (14)
N50.054 (2)0.0652 (19)0.0534 (19)0.0045 (16)0.0028 (16)0.0081 (15)
N60.061 (2)0.079 (2)0.060 (2)0.0043 (18)0.0059 (18)0.0026 (18)
N70.065 (2)0.074 (2)0.0488 (18)0.0049 (18)0.0078 (17)0.0009 (16)
N80.059 (2)0.0502 (16)0.0415 (17)0.0043 (15)0.0006 (15)0.0009 (13)
C10.050 (2)0.0373 (17)0.053 (2)0.0057 (15)0.0069 (17)0.0012 (15)
C20.058 (3)0.0426 (19)0.082 (3)0.0020 (18)0.011 (2)0.0177 (19)
C30.048 (2)0.0351 (18)0.105 (3)0.0048 (17)0.004 (2)0.005 (2)
C40.051 (2)0.048 (2)0.084 (3)0.0062 (18)0.002 (2)0.028 (2)
C50.041 (2)0.053 (2)0.054 (2)0.0019 (17)0.0039 (17)0.0079 (17)
C60.0331 (17)0.0330 (15)0.0474 (19)0.0025 (13)0.0014 (15)0.0003 (15)
C70.0434 (19)0.0329 (16)0.0409 (18)0.0014 (14)0.0033 (15)0.0022 (14)
C80.053 (2)0.0352 (16)0.050 (2)0.0058 (15)0.0018 (17)0.0031 (15)
C90.068 (2)0.0391 (18)0.048 (2)0.0053 (17)0.0028 (18)0.0001 (16)
C100.071 (3)0.0448 (19)0.0412 (19)0.0001 (18)0.0012 (18)0.0072 (16)
C110.049 (2)0.0452 (18)0.0424 (18)0.0024 (16)0.0042 (16)0.0112 (15)
C120.055 (2)0.0448 (18)0.047 (2)0.0020 (18)0.0025 (18)0.0069 (16)
C130.070 (3)0.0470 (19)0.0319 (18)0.0016 (19)0.0020 (17)0.0019 (15)
C140.093 (3)0.056 (2)0.041 (2)0.008 (2)0.004 (2)0.0069 (18)
C150.126 (4)0.056 (2)0.050 (2)0.002 (3)0.008 (3)0.0134 (19)
C160.114 (4)0.075 (3)0.042 (2)0.025 (3)0.006 (3)0.006 (2)
C170.084 (3)0.084 (3)0.044 (2)0.001 (2)0.014 (2)0.000 (2)
C180.080 (3)0.058 (2)0.045 (2)0.009 (2)0.011 (2)0.0048 (18)
Geometric parameters (Å, º) top
S1—C71.743 (3)C4—C51.395 (5)
S1—C81.818 (3)C4—H40.9300
S2—C121.739 (4)C5—C61.377 (4)
S2—C111.812 (3)C5—H50.9300
O1—C101.417 (3)C8—C91.502 (4)
O1—C91.422 (3)C8—H8A0.9700
N1—C71.351 (4)C8—H8B0.9700
N1—N21.366 (3)C9—H9A0.9700
N1—C61.442 (3)C9—H9B0.9700
N2—N31.297 (4)C10—C111.513 (4)
N3—N41.372 (4)C10—H10A0.9700
N4—C71.328 (4)C10—H10B0.9700
N5—C121.329 (4)C11—H11A0.9700
N5—N61.370 (4)C11—H11B0.9700
N6—N71.290 (4)C13—C181.382 (5)
N7—N81.363 (4)C13—C141.387 (4)
N8—C121.352 (4)C14—C151.385 (5)
N8—C131.438 (4)C14—H140.9300
C1—C61.377 (4)C15—C161.375 (6)
C1—C21.385 (4)C15—H150.9300
C1—H10.9300C16—C171.380 (5)
C2—C31.371 (5)C16—H160.9300
C2—H20.9300C17—C181.382 (5)
C3—C41.371 (5)C17—H170.9300
C3—H30.9300C18—H180.9300
C7—S1—C899.19 (15)H8A—C8—H8B107.9
C12—S2—C11100.56 (16)O1—C9—C8107.7 (2)
C10—O1—C9111.7 (2)O1—C9—H9A110.2
C7—N1—N2108.4 (2)C8—C9—H9A110.2
C7—N1—C6130.1 (3)O1—C9—H9B110.2
N2—N1—C6121.4 (2)C8—C9—H9B110.2
N3—N2—N1105.9 (2)H9A—C9—H9B108.5
N2—N3—N4111.6 (3)O1—C10—C11108.0 (2)
C7—N4—N3105.4 (2)O1—C10—H10A110.1
C12—N5—N6106.1 (3)C11—C10—H10A110.1
N7—N6—N5110.9 (3)O1—C10—H10B110.1
N6—N7—N8106.7 (3)C11—C10—H10B110.1
C12—N8—N7108.2 (3)H10A—C10—H10B108.4
C12—N8—C13130.9 (3)C10—C11—S2111.8 (2)
N7—N8—C13120.8 (3)C10—C11—H11A109.3
C6—C1—C2118.8 (3)S2—C11—H11A109.3
C6—C1—H1120.6C10—C11—H11B109.3
C2—C1—H1120.6S2—C11—H11B109.3
C3—C2—C1119.8 (3)H11A—C11—H11B107.9
C3—C2—H2120.1N5—C12—N8108.1 (3)
C1—C2—H2120.1N5—C12—S2127.4 (3)
C2—C3—C4120.9 (3)N8—C12—S2124.5 (3)
C2—C3—H3119.6C18—C13—C14121.3 (3)
C4—C3—H3119.6C18—C13—N8120.4 (3)
C3—C4—C5120.4 (3)C14—C13—N8118.2 (3)
C3—C4—H4119.8C15—C14—C13118.6 (4)
C5—C4—H4119.8C15—C14—H14120.7
C6—C5—C4117.7 (3)C13—C14—H14120.7
C6—C5—H5121.1C16—C15—C14120.6 (4)
C4—C5—H5121.1C16—C15—H15119.7
C5—C6—C1122.3 (3)C14—C15—H15119.7
C5—C6—N1119.0 (3)C15—C16—C17120.1 (4)
C1—C6—N1118.6 (3)C15—C16—H16119.9
N4—C7—N1108.7 (3)C17—C16—H16119.9
N4—C7—S1128.1 (2)C16—C17—C18120.4 (4)
N1—C7—S1123.2 (2)C16—C17—H17119.8
C9—C8—S1112.3 (2)C18—C17—H17119.8
C9—C8—H8A109.1C17—C18—C13118.9 (4)
S1—C8—H8A109.1C17—C18—H18120.6
C9—C8—H8B109.1C13—C18—H18120.6
S1—C8—H8B109.1
C7—N1—N2—N30.1 (3)C8—S1—C7—N1179.8 (3)
C6—N1—N2—N3175.6 (3)C7—S1—C8—C986.0 (3)
N1—N2—N3—N40.0 (4)C10—O1—C9—C8172.2 (3)
N2—N3—N4—C70.1 (4)S1—C8—C9—O1178.9 (2)
C12—N5—N6—N70.5 (4)C9—O1—C10—C11176.8 (3)
N5—N6—N7—N80.8 (4)O1—C10—C11—S2174.6 (2)
N6—N7—N8—C120.8 (4)C12—S2—C11—C1073.3 (3)
N6—N7—N8—C13178.1 (3)N6—N5—C12—N80.1 (4)
C6—C1—C2—C31.4 (5)N6—N5—C12—S2178.3 (3)
C1—C2—C3—C40.7 (6)N7—N8—C12—N50.6 (4)
C2—C3—C4—C50.8 (6)C13—N8—C12—N5177.5 (3)
C3—C4—C5—C61.6 (5)N7—N8—C12—S2177.9 (2)
C4—C5—C6—C10.9 (5)C13—N8—C12—S21.0 (5)
C4—C5—C6—N1176.8 (3)C11—S2—C12—N50.3 (3)
C2—C1—C6—C50.6 (5)C11—S2—C12—N8178.4 (3)
C2—C1—C6—N1178.3 (3)C12—N8—C13—C1846.1 (5)
C7—N1—C6—C5121.5 (3)N7—N8—C13—C18137.3 (3)
N2—N1—C6—C564.1 (4)C12—N8—C13—C14134.3 (4)
C7—N1—C6—C160.6 (4)N7—N8—C13—C1442.3 (4)
N2—N1—C6—C1113.8 (3)C18—C13—C14—C150.1 (5)
N3—N4—C7—N10.1 (3)N8—C13—C14—C15179.7 (3)
N3—N4—C7—S1178.6 (2)C13—C14—C15—C160.6 (6)
N2—N1—C7—N40.2 (3)C14—C15—C16—C170.3 (6)
C6—N1—C7—N4175.1 (3)C15—C16—C17—C180.7 (6)
N2—N1—C7—S1178.7 (2)C16—C17—C18—C131.4 (6)
C6—N1—C7—S16.3 (4)C14—C13—C18—C171.1 (5)
C8—S1—C7—N41.6 (3)N8—C13—C18—C17179.3 (3)
 

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