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In the title compound, C11H9N5OS, the mol­ecules are linked into chains along the c axis via N—H...N hydrogen bonds. The packing is further stabilized by C—H...π and π–π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806035720/sg2056sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806035720/sg2056Isup2.hkl
Contains datablock I

CCDC reference: 624976

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.039
  • wR factor = 0.103
  • Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

5-[(4-Phenyl-1H-1,2,3-triazol-1-yl)methyl]-1,3,4-oxadiazole-2-thione top
Crystal data top
C11H9N5OSZ = 2
Mr = 259.29F(000) = 268
Triclinic, P1Dx = 1.461 Mg m3
a = 8.3037 (15) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.5820 (15) ÅCell parameters from 2040 reflections
c = 8.7191 (15) Åθ = 2.5–26.0°
α = 105.911 (2)°µ = 0.27 mm1
β = 97.441 (2)°T = 293 K
γ = 93.643 (2)°Plate, yellow
V = 589.30 (18) Å30.38 × 0.29 × 0.11 mm
Data collection top
Siemens SMART 1000 CCD area-detector
diffractometer
2245 independent reflections
Radiation source: fine-focus sealed tube2003 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.009
Detector resolution: 8.33 pixels mm-1θmax = 26.0°, θmin = 2.5°
ω scansh = 1010
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1010
Tmin = 0.905, Tmax = 0.971l = 510
3267 measured reflections
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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0525P)2 + 0.1861P]
where P = (Fo2 + 2Fc2)/3
2245 reflections(Δ/σ)max < 0.001
167 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.32 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
S10.29204 (7)0.63768 (6)0.03357 (6)0.06055 (19)
O10.13769 (14)0.44271 (14)0.17196 (13)0.0438 (3)
N10.20888 (19)0.20941 (17)0.60543 (16)0.0451 (3)
N20.1204 (2)0.28433 (18)0.51733 (17)0.0498 (4)
N30.08677 (17)0.17999 (18)0.36785 (16)0.0440 (3)
N40.10558 (19)0.20099 (17)0.00865 (17)0.0469 (4)
N50.18942 (19)0.31624 (18)0.06181 (17)0.0449 (4)
C10.4247 (2)0.0055 (2)0.7260 (2)0.0495 (4)
H1B0.44230.10460.78230.059*
C20.5023 (2)0.1179 (3)0.7882 (2)0.0599 (5)
H2B0.57160.08270.88650.072*
C30.4780 (3)0.2808 (3)0.7067 (3)0.0615 (5)
H3A0.52980.35560.74990.074*
C40.3767 (3)0.3330 (3)0.5606 (3)0.0614 (5)
H4B0.36060.44320.50470.074*
C50.2989 (2)0.2222 (2)0.4967 (2)0.0514 (4)
H5B0.23150.25840.39740.062*
C60.32031 (19)0.0571 (2)0.57920 (18)0.0391 (4)
C70.23157 (19)0.05822 (19)0.51350 (18)0.0381 (3)
C80.1523 (2)0.0399 (2)0.36038 (19)0.0437 (4)
H8A0.14550.05030.27070.052*
C90.0167 (2)0.2240 (3)0.2404 (2)0.0522 (5)
H9A0.08160.30880.28950.063*
H9B0.09130.12980.17800.063*
C100.0782 (2)0.2824 (2)0.12990 (19)0.0415 (4)
C110.2083 (2)0.4632 (2)0.04258 (19)0.0407 (4)
H5A0.211 (3)0.287 (3)0.160 (3)0.066 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0749 (4)0.0489 (3)0.0579 (3)0.0069 (2)0.0079 (2)0.0195 (2)
O10.0551 (7)0.0456 (6)0.0289 (5)0.0025 (5)0.0083 (5)0.0074 (5)
N10.0616 (9)0.0443 (8)0.0291 (7)0.0059 (6)0.0071 (6)0.0100 (6)
N20.0674 (10)0.0483 (8)0.0348 (7)0.0074 (7)0.0091 (7)0.0127 (6)
N30.0505 (8)0.0540 (9)0.0305 (7)0.0014 (6)0.0074 (6)0.0175 (6)
N40.0637 (9)0.0428 (8)0.0357 (7)0.0021 (7)0.0080 (6)0.0142 (6)
N50.0654 (9)0.0433 (8)0.0278 (7)0.0046 (7)0.0129 (6)0.0107 (6)
C10.0514 (10)0.0560 (10)0.0373 (9)0.0033 (8)0.0042 (7)0.0089 (8)
C20.0563 (11)0.0834 (15)0.0424 (10)0.0168 (10)0.0057 (8)0.0206 (10)
C30.0617 (12)0.0734 (14)0.0645 (13)0.0269 (10)0.0230 (10)0.0341 (11)
C40.0661 (12)0.0492 (11)0.0695 (13)0.0146 (9)0.0174 (10)0.0128 (10)
C50.0566 (10)0.0497 (10)0.0430 (9)0.0063 (8)0.0078 (8)0.0051 (8)
C60.0417 (8)0.0466 (9)0.0301 (8)0.0011 (7)0.0113 (6)0.0108 (7)
C70.0442 (8)0.0422 (8)0.0271 (7)0.0019 (6)0.0098 (6)0.0083 (6)
C80.0529 (9)0.0478 (9)0.0288 (8)0.0010 (7)0.0086 (7)0.0084 (7)
C90.0497 (10)0.0726 (13)0.0417 (9)0.0027 (9)0.0055 (8)0.0300 (9)
C100.0485 (9)0.0452 (9)0.0315 (8)0.0030 (7)0.0016 (7)0.0145 (7)
C110.0487 (9)0.0456 (9)0.0290 (7)0.0064 (7)0.0031 (6)0.0136 (7)
Geometric parameters (Å, º) top
S1—C111.6364 (18)C2—C31.372 (3)
O1—C101.364 (2)C2—H2B0.9300
O1—C111.384 (2)C3—C41.375 (3)
N1—N21.314 (2)C3—H3A0.9300
N1—C71.364 (2)C4—C51.381 (3)
N2—N31.346 (2)C4—H4B0.9300
N3—C81.340 (2)C5—C61.390 (2)
N3—C91.463 (2)C5—H5B0.9300
N4—C101.276 (2)C6—C71.464 (2)
N4—N51.388 (2)C7—C81.373 (2)
N5—C111.324 (2)C8—H8A0.9300
N5—H5A0.87 (2)C9—C101.487 (2)
C1—C21.384 (3)C9—H9A0.9700
C1—C61.393 (2)C9—H9B0.9700
C1—H1B0.9300
C10—O1—C11105.78 (12)C4—C5—H5B119.6
N2—N1—C7110.05 (13)C6—C5—H5B119.6
N1—N2—N3106.06 (14)C5—C6—C1118.52 (17)
C8—N3—N2111.57 (13)C5—C6—C7120.20 (15)
C8—N3—C9128.36 (15)C1—C6—C7121.27 (15)
N2—N3—C9120.01 (15)N1—C7—C8107.15 (15)
C10—N4—N5103.24 (14)N1—C7—C6122.90 (14)
C11—N5—N4112.74 (14)C8—C7—C6129.91 (15)
C11—N5—H5A129.1 (15)N3—C8—C7105.17 (14)
N4—N5—H5A117.6 (15)N3—C8—H8A127.4
C2—C1—C6120.04 (18)C7—C8—H8A127.4
C2—C1—H1B120.0N3—C9—C10112.98 (14)
C6—C1—H1B120.0N3—C9—H9A109.0
C3—C2—C1120.78 (19)C10—C9—H9A109.0
C3—C2—H2B119.6N3—C9—H9B109.0
C1—C2—H2B119.6C10—C9—H9B109.0
C2—C3—C4119.67 (19)H9A—C9—H9B107.8
C2—C3—H3A120.2N4—C10—O1113.61 (15)
C4—C3—H3A120.2N4—C10—C9127.46 (17)
C3—C4—C5120.21 (19)O1—C10—C9118.82 (15)
C3—C4—H4B119.9N5—C11—O1104.60 (14)
C5—C4—H4B119.9N5—C11—S1131.26 (13)
C4—C5—C6120.76 (18)O1—C11—S1124.14 (12)
C7—N1—N2—N30.13 (18)C1—C6—C7—C8164.74 (17)
N1—N2—N3—C80.22 (19)N2—N3—C8—C70.22 (19)
N1—N2—N3—C9177.47 (14)C9—N3—C8—C7177.19 (15)
C10—N4—N5—C111.09 (19)N1—C7—C8—N30.13 (18)
C6—C1—C2—C30.1 (3)C6—C7—C8—N3177.60 (16)
C1—C2—C3—C40.7 (3)C8—N3—C9—C1082.8 (2)
C2—C3—C4—C50.4 (3)N2—N3—C9—C10100.47 (19)
C3—C4—C5—C60.6 (3)N5—N4—C10—O10.02 (19)
C4—C5—C6—C11.4 (3)N5—N4—C10—C9176.17 (16)
C4—C5—C6—C7177.33 (17)C11—O1—C10—N40.97 (19)
C2—C1—C6—C51.1 (3)C11—O1—C10—C9175.54 (14)
C2—C1—C6—C7177.55 (17)N3—C9—C10—N498.7 (2)
N2—N1—C7—C80.01 (18)N3—C9—C10—O185.3 (2)
N2—N1—C7—C6177.69 (15)N4—N5—C11—O11.67 (19)
C5—C6—C7—N1160.51 (16)N4—N5—C11—S1177.87 (13)
C1—C6—C7—N118.1 (2)C10—O1—C11—N51.54 (17)
C5—C6—C7—C816.6 (3)C10—O1—C11—S1178.04 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3A···Cg1i0.932.983.682133
N5—H5A···N1ii0.87 (2)1.97 (2)2.822 (2)168 (2)
Symmetry codes: (i) x+1, y, z+1; (ii) x, y, z1.
 

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