5-[(4-Phenyl-1H-1,2,3-triazol-1-yl)methyl]-1,3,4-oxadiazole-2-thione

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.

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

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Computing details

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

Crystal data

C11H9N5OS	Z = 2
Mr = 259.29	F(000) = 268
Triclinic, P1	Dx = 1.461 Mg m^−3
a = 8.3037 (15) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.5820 (15) Å	Cell parameters from 2040 reflections
c = 8.7191 (15) Å	θ = 2.5–26.0°
α = 105.911 (2)°	µ = 0.27 mm^−1
β = 97.441 (2)°	T = 293 K
γ = 93.643 (2)°	Plate, yellow
V = 589.30 (18) Å^3	0.38 × 0.29 × 0.11 mm

Data collection

Siemens SMART 1000 CCD area-detector diffractometer	2245 independent reflections
Radiation source: fine-focus sealed tube	2003 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.009
Detector resolution: 8.33 pixels mm^-1	θmax = 26.0°, θmin = 2.5°
ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −10→10
Tmin = 0.905, Tmax = 0.971	l = −5→10
3267 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0525P)^2 + 0.1861P] where P = (Fo^2 + 2Fc^2)/3
2245 reflections	(Δ/σ)max < 0.001
167 parameters	Δρmax = 0.20 e Å^−3
0 restraints	Δρmin = −0.32 e Å^−3

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	0.29204 (7)	0.63768 (6)	0.03357 (6)	0.06055 (19)
O1	0.13769 (14)	0.44271 (14)	0.17196 (13)	0.0438 (3)
N1	0.20888 (19)	0.20941 (17)	0.60543 (16)	0.0451 (3)
N2	0.1204 (2)	0.28433 (18)	0.51733 (17)	0.0498 (4)
N3	0.08677 (17)	0.17999 (18)	0.36785 (16)	0.0440 (3)
N4	0.10558 (19)	0.20099 (17)	−0.00865 (17)	0.0469 (4)
N5	0.18942 (19)	0.31624 (18)	−0.06181 (17)	0.0449 (4)
C1	0.4247 (2)	−0.0055 (2)	0.7260 (2)	0.0495 (4)
H1B	0.4423	0.1046	0.7823	0.059*
C2	0.5023 (2)	−0.1179 (3)	0.7882 (2)	0.0599 (5)
H2B	0.5716	−0.0827	0.8865	0.072*
C3	0.4780 (3)	−0.2808 (3)	0.7067 (3)	0.0615 (5)
H3A	0.5298	−0.3556	0.7499	0.074*
C4	0.3767 (3)	−0.3330 (3)	0.5606 (3)	0.0614 (5)
H4B	0.3606	−0.4432	0.5047	0.074*
C5	0.2989 (2)	−0.2222 (2)	0.4967 (2)	0.0514 (4)
H5B	0.2315	−0.2584	0.3974	0.062*
C6	0.32031 (19)	−0.0571 (2)	0.57920 (18)	0.0391 (4)
C7	0.23157 (19)	0.05822 (19)	0.51350 (18)	0.0381 (3)
C8	0.1523 (2)	0.0399 (2)	0.36038 (19)	0.0437 (4)
H8A	0.1455	−0.0503	0.2707	0.052*
C9	−0.0167 (2)	0.2240 (3)	0.2404 (2)	0.0522 (5)
H9A	−0.0816	0.3088	0.2895	0.063*
H9B	−0.0913	0.1298	0.1780	0.063*
C10	0.0782 (2)	0.2824 (2)	0.12990 (19)	0.0415 (4)
C11	0.2083 (2)	0.4632 (2)	0.04258 (19)	0.0407 (4)
H5A	0.211 (3)	0.287 (3)	−0.160 (3)	0.066 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0749 (4)	0.0489 (3)	0.0579 (3)	−0.0069 (2)	0.0079 (2)	0.0195 (2)
O1	0.0551 (7)	0.0456 (6)	0.0289 (5)	0.0025 (5)	0.0083 (5)	0.0074 (5)
N1	0.0616 (9)	0.0443 (8)	0.0291 (7)	0.0059 (6)	0.0071 (6)	0.0100 (6)
N2	0.0674 (10)	0.0483 (8)	0.0348 (7)	0.0074 (7)	0.0091 (7)	0.0127 (6)
N3	0.0505 (8)	0.0540 (9)	0.0305 (7)	0.0014 (6)	0.0074 (6)	0.0175 (6)
N4	0.0637 (9)	0.0428 (8)	0.0357 (7)	0.0021 (7)	0.0080 (6)	0.0142 (6)
N5	0.0654 (9)	0.0433 (8)	0.0278 (7)	0.0046 (7)	0.0129 (6)	0.0107 (6)
C1	0.0514 (10)	0.0560 (10)	0.0373 (9)	0.0033 (8)	0.0042 (7)	0.0089 (8)
C2	0.0563 (11)	0.0834 (15)	0.0424 (10)	0.0168 (10)	0.0057 (8)	0.0206 (10)
C3	0.0617 (12)	0.0734 (14)	0.0645 (13)	0.0269 (10)	0.0230 (10)	0.0341 (11)
C4	0.0661 (12)	0.0492 (11)	0.0695 (13)	0.0146 (9)	0.0174 (10)	0.0128 (10)
C5	0.0566 (10)	0.0497 (10)	0.0430 (9)	0.0063 (8)	0.0078 (8)	0.0051 (8)
C6	0.0417 (8)	0.0466 (9)	0.0301 (8)	0.0011 (7)	0.0113 (6)	0.0108 (7)
C7	0.0442 (8)	0.0422 (8)	0.0271 (7)	−0.0019 (6)	0.0098 (6)	0.0083 (6)
C8	0.0529 (9)	0.0478 (9)	0.0288 (8)	0.0010 (7)	0.0086 (7)	0.0084 (7)
C9	0.0497 (10)	0.0726 (13)	0.0417 (9)	0.0027 (9)	0.0055 (8)	0.0300 (9)
C10	0.0485 (9)	0.0452 (9)	0.0315 (8)	0.0030 (7)	0.0016 (7)	0.0145 (7)
C11	0.0487 (9)	0.0456 (9)	0.0290 (7)	0.0064 (7)	0.0031 (6)	0.0136 (7)

Geometric parameters (Å, º)

S1—C11	1.6364 (18)	C2—C3	1.372 (3)
O1—C10	1.364 (2)	C2—H2B	0.9300
O1—C11	1.384 (2)	C3—C4	1.375 (3)
N1—N2	1.314 (2)	C3—H3A	0.9300
N1—C7	1.364 (2)	C4—C5	1.381 (3)
N2—N3	1.346 (2)	C4—H4B	0.9300
N3—C8	1.340 (2)	C5—C6	1.390 (2)
N3—C9	1.463 (2)	C5—H5B	0.9300
N4—C10	1.276 (2)	C6—C7	1.464 (2)
N4—N5	1.388 (2)	C7—C8	1.373 (2)
N5—C11	1.324 (2)	C8—H8A	0.9300
N5—H5A	0.87 (2)	C9—C10	1.487 (2)
C1—C2	1.384 (3)	C9—H9A	0.9700
C1—C6	1.393 (2)	C9—H9B	0.9700
C1—H1B	0.9300
C10—O1—C11	105.78 (12)	C4—C5—H5B	119.6
N2—N1—C7	110.05 (13)	C6—C5—H5B	119.6
N1—N2—N3	106.06 (14)	C5—C6—C1	118.52 (17)
C8—N3—N2	111.57 (13)	C5—C6—C7	120.20 (15)
C8—N3—C9	128.36 (15)	C1—C6—C7	121.27 (15)
N2—N3—C9	120.01 (15)	N1—C7—C8	107.15 (15)
C10—N4—N5	103.24 (14)	N1—C7—C6	122.90 (14)
C11—N5—N4	112.74 (14)	C8—C7—C6	129.91 (15)
C11—N5—H5A	129.1 (15)	N3—C8—C7	105.17 (14)
N4—N5—H5A	117.6 (15)	N3—C8—H8A	127.4
C2—C1—C6	120.04 (18)	C7—C8—H8A	127.4
C2—C1—H1B	120.0	N3—C9—C10	112.98 (14)
C6—C1—H1B	120.0	N3—C9—H9A	109.0
C3—C2—C1	120.78 (19)	C10—C9—H9A	109.0
C3—C2—H2B	119.6	N3—C9—H9B	109.0
C1—C2—H2B	119.6	C10—C9—H9B	109.0
C2—C3—C4	119.67 (19)	H9A—C9—H9B	107.8
C2—C3—H3A	120.2	N4—C10—O1	113.61 (15)
C4—C3—H3A	120.2	N4—C10—C9	127.46 (17)
C3—C4—C5	120.21 (19)	O1—C10—C9	118.82 (15)
C3—C4—H4B	119.9	N5—C11—O1	104.60 (14)
C5—C4—H4B	119.9	N5—C11—S1	131.26 (13)
C4—C5—C6	120.76 (18)	O1—C11—S1	124.14 (12)
C7—N1—N2—N3	−0.13 (18)	C1—C6—C7—C8	164.74 (17)
N1—N2—N3—C8	0.22 (19)	N2—N3—C8—C7	−0.22 (19)
N1—N2—N3—C9	177.47 (14)	C9—N3—C8—C7	−177.19 (15)
C10—N4—N5—C11	−1.09 (19)	N1—C7—C8—N3	0.13 (18)
C6—C1—C2—C3	0.1 (3)	C6—C7—C8—N3	177.60 (16)
C1—C2—C3—C4	0.7 (3)	C8—N3—C9—C10	−82.8 (2)
C2—C3—C4—C5	−0.4 (3)	N2—N3—C9—C10	100.47 (19)
C3—C4—C5—C6	−0.6 (3)	N5—N4—C10—O1	0.02 (19)
C4—C5—C6—C1	1.4 (3)	N5—N4—C10—C9	176.17 (16)
C4—C5—C6—C7	−177.33 (17)	C11—O1—C10—N4	0.97 (19)
C2—C1—C6—C5	−1.1 (3)	C11—O1—C10—C9	−175.54 (14)
C2—C1—C6—C7	177.55 (17)	N3—C9—C10—N4	98.7 (2)
N2—N1—C7—C8	−0.01 (18)	N3—C9—C10—O1	−85.3 (2)
N2—N1—C7—C6	−177.69 (15)	N4—N5—C11—O1	1.67 (19)
C5—C6—C7—N1	160.51 (16)	N4—N5—C11—S1	−177.87 (13)
C1—C6—C7—N1	−18.1 (2)	C10—O1—C11—N5	−1.54 (17)
C5—C6—C7—C8	−16.6 (3)	C10—O1—C11—S1	178.04 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···Cg1^i	0.93	2.98	3.682	133
N5—H5A···N1^ii	0.87 (2)	1.97 (2)	2.822 (2)	168 (2)

Symmetry codes: (i) −x+1, −y, −z+1; (ii) x, y, z−1.