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

The title compound, C₁₁H₁₀N₆S, was prepared by the reaction of ethyl 2-(1H-1,2,4-triazol-1-yl)­acetate with hydrazine and phenyl iso­thio­cyanate. The molecular structure and packing are stabilized by an N—H...N intermolecular hydrogen-bond and C—H...π interactions.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.034
• wR factor = 0.084
• Data-to-parameter ratio = 12.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H1A    ..  CG1     ..       2.99 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H4A    ..  CG2     ..       2.98 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5B    ..  CG1     ..       2.83 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 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
   0 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXL (Sheldrick, 1990); software used to prepare material for publication: WinGX (Farrugia, 1999).

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

Crystal data

C11H10N6S	F(000) = 536
Mr = 258.31	Dx = 1.437 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -p 2y bc	Cell parameters from 25 reflections
a = 9.0010 (18) Å	θ = 4–14°
b = 9.5510 (19) Å	µ = 0.26 mm^−1
c = 14.251 (3) Å	T = 295 K
β = 102.94 (3)°	Block, yellow
V = 1194.0 (4) Å^3	0.35 × 0.25 × 0.20 mm
Z = 4

Data collection

Enraf–Nonius CAD-4 diffractometer	Rint = 0.033
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 2.3°
Graphite monochromator	h = 0→10
ω scans	k = −11→11
4343 measured reflections	l = −16→16
2104 independent reflections	3 standard reflections every 100 reflections
1449 reflections with I > 2σ(I)	intensity decay: 0.1%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.034	H-atom parameters constrained
wR(F^2) = 0.084	w = 1/[σ^2(Fo^2) + (0.0347P)^2 + 0.2841P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
2104 reflections	Δρmax = 0.17 e Å^−3
164 parameters	Δρmin = −0.17 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0035 (7)

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	0.29680 (6)	0.07604 (7)	0.39013 (4)	0.04435 (19)
N1	0.45042 (17)	0.15671 (17)	0.25261 (11)	0.0311 (4)
N2	0.21187 (18)	0.12975 (18)	0.19890 (13)	0.0382 (4)
H2A	0.1166	0.1152	0.1959	0.046*
N3	0.26807 (18)	0.16429 (19)	0.11972 (13)	0.0387 (4)
N4	0.66003 (17)	0.14250 (19)	0.11338 (12)	0.0335 (4)
N5	0.65776 (19)	0.0007 (2)	0.10175 (13)	0.0444 (5)
N6	0.89804 (18)	0.0800 (2)	0.15137 (13)	0.0439 (5)
C1	0.6894 (2)	0.0491 (2)	0.33537 (16)	0.0413 (5)
H1A	0.6515	−0.0375	0.3116	0.050*
C2	0.8358 (2)	0.0609 (3)	0.39097 (17)	0.0490 (6)
H2B	0.8971	−0.0182	0.4047	0.059*
C3	0.8908 (2)	0.1894 (3)	0.42609 (16)	0.0464 (6)
H3B	0.9903	0.1975	0.4621	0.056*
C4	0.7994 (3)	0.3058 (3)	0.40817 (16)	0.0470 (6)
H4A	0.8362	0.3921	0.4334	0.056*
C5	0.6523 (2)	0.2951 (2)	0.35256 (15)	0.0394 (5)
H5B	0.5897	0.3735	0.3405	0.047*
C6	0.6003 (2)	0.1671 (2)	0.31563 (14)	0.0309 (5)
C7	0.3182 (2)	0.1208 (2)	0.28073 (15)	0.0326 (5)
C8	0.4127 (2)	0.1807 (2)	0.15455 (15)	0.0320 (5)
C9	0.5204 (2)	0.2240 (2)	0.09397 (15)	0.0381 (5)
H9A	0.4703	0.2138	0.0266	0.046*
H9B	0.5456	0.3221	0.1056	0.046*
C10	0.8037 (2)	−0.0299 (3)	0.12498 (16)	0.0455 (6)
H10A	0.8396	−0.1210	0.1233	0.055*
C11	0.8027 (2)	0.1869 (2)	0.14279 (15)	0.0387 (5)
H11A	0.8314	0.2797	0.1555	0.046*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0408 (3)	0.0499 (4)	0.0454 (3)	−0.0016 (3)	0.0162 (3)	0.0007 (3)
N1	0.0219 (8)	0.0341 (10)	0.0369 (10)	−0.0002 (7)	0.0056 (7)	0.0005 (8)
N2	0.0207 (9)	0.0483 (11)	0.0464 (11)	−0.0012 (8)	0.0095 (8)	−0.0007 (9)
N3	0.0247 (9)	0.0467 (11)	0.0441 (11)	0.0011 (8)	0.0064 (8)	0.0023 (9)
N4	0.0238 (9)	0.0402 (11)	0.0367 (10)	−0.0020 (8)	0.0070 (7)	0.0013 (8)
N5	0.0333 (10)	0.0438 (13)	0.0554 (12)	−0.0016 (9)	0.0086 (9)	−0.0036 (10)
N6	0.0255 (9)	0.0568 (13)	0.0498 (11)	−0.0006 (10)	0.0094 (8)	0.0003 (10)
C1	0.0373 (12)	0.0368 (14)	0.0477 (13)	0.0015 (10)	0.0049 (10)	0.0043 (10)
C2	0.0377 (13)	0.0522 (16)	0.0530 (14)	0.0134 (11)	0.0013 (11)	0.0109 (12)
C3	0.0292 (12)	0.0666 (18)	0.0393 (13)	−0.0015 (12)	−0.0013 (10)	0.0084 (12)
C4	0.0425 (13)	0.0461 (15)	0.0475 (14)	−0.0105 (11)	0.0001 (11)	−0.0021 (11)
C5	0.0340 (12)	0.0359 (13)	0.0453 (13)	0.0028 (10)	0.0026 (10)	−0.0001 (10)
C6	0.0220 (10)	0.0375 (13)	0.0329 (11)	−0.0017 (9)	0.0052 (8)	0.0031 (9)
C7	0.0252 (10)	0.0300 (11)	0.0429 (12)	0.0017 (8)	0.0081 (9)	−0.0033 (9)
C8	0.0245 (10)	0.0320 (12)	0.0389 (12)	0.0021 (9)	0.0057 (9)	0.0015 (9)
C9	0.0261 (11)	0.0460 (14)	0.0416 (12)	0.0008 (10)	0.0063 (9)	0.0071 (11)
C10	0.0341 (12)	0.0479 (14)	0.0547 (15)	0.0039 (11)	0.0103 (11)	−0.0029 (12)
C11	0.0265 (11)	0.0483 (14)	0.0415 (13)	−0.0091 (10)	0.0081 (10)	−0.0014 (10)

Geometric parameters (Å, º)

S1—C7	1.669 (2)	C1—C2	1.382 (3)
N1—C8	1.381 (3)	C1—H1A	0.9300
N1—C7	1.382 (2)	C2—C3	1.376 (3)
N1—C6	1.447 (2)	C2—H2B	0.9300
N2—C7	1.335 (3)	C3—C4	1.373 (3)
N2—N3	1.376 (2)	C3—H3B	0.9300
N2—H2A	0.8600	C4—C5	1.386 (3)
N3—C8	1.295 (2)	C4—H4A	0.9300
N4—C11	1.328 (2)	C5—C6	1.371 (3)
N4—N5	1.364 (2)	C5—H5B	0.9300
N4—C9	1.451 (2)	C8—C9	1.493 (3)
N5—C10	1.314 (3)	C9—H9A	0.9700
N6—C11	1.321 (3)	C9—H9B	0.9700
N6—C10	1.350 (3)	C10—H10A	0.9300
C1—C6	1.375 (3)	C11—H11A	0.9300
C8—N1—C7	107.60 (16)	C6—C5—C4	119.1 (2)
C8—N1—C6	126.87 (16)	C6—C5—H5B	120.5
C7—N1—C6	125.53 (16)	C4—C5—H5B	120.5
C7—N2—N3	114.10 (16)	C5—C6—C1	121.27 (18)
C7—N2—H2A	123.0	C5—C6—N1	119.34 (18)
N3—N2—H2A	123.0	C1—C6—N1	119.38 (18)
C8—N3—N2	103.74 (17)	N2—C7—N1	103.08 (17)
C11—N4—N5	110.01 (17)	N2—C7—S1	128.48 (16)
C11—N4—C9	128.62 (19)	N1—C7—S1	128.44 (15)
N5—N4—C9	121.37 (16)	N3—C8—N1	111.45 (18)
C10—N5—N4	101.71 (17)	N3—C8—C9	122.61 (19)
C11—N6—C10	102.72 (17)	N1—C8—C9	125.92 (17)
C6—C1—C2	119.2 (2)	N4—C9—C8	112.81 (17)
C6—C1—H1A	120.4	N4—C9—H9A	109.0
C2—C1—H1A	120.4	C8—C9—H9A	109.0
C3—C2—C1	120.0 (2)	N4—C9—H9B	109.0
C3—C2—H2B	120.0	C8—C9—H9B	109.0
C1—C2—H2B	120.0	H9A—C9—H9B	107.8
C4—C3—C2	120.2 (2)	N5—C10—N6	115.4 (2)
C4—C3—H3B	119.9	N5—C10—H10A	122.3
C2—C3—H3B	119.9	N6—C10—H10A	122.3
C3—C4—C5	120.2 (2)	N6—C11—N4	110.2 (2)
C3—C4—H4A	119.9	N6—C11—H11A	124.9
C5—C4—H4A	119.9	N4—C11—H11A	124.9
C7—N2—N3—C8	−1.7 (2)	C6—N1—C7—N2	178.19 (17)
C11—N4—N5—C10	−0.5 (2)	C8—N1—C7—S1	177.90 (15)
C9—N4—N5—C10	179.13 (18)	C6—N1—C7—S1	−2.2 (3)
C6—C1—C2—C3	0.1 (3)	N2—N3—C8—N1	0.5 (2)
C1—C2—C3—C4	1.7 (4)	N2—N3—C8—C9	−177.97 (18)
C2—C3—C4—C5	−1.6 (3)	C7—N1—C8—N3	0.8 (2)
C3—C4—C5—C6	−0.3 (3)	C6—N1—C8—N3	−179.10 (18)
C4—C5—C6—C1	2.2 (3)	C7—N1—C8—C9	179.15 (19)
C4—C5—C6—N1	−176.16 (19)	C6—N1—C8—C9	−0.7 (3)
C2—C1—C6—C5	−2.1 (3)	C11—N4—C9—C8	−121.0 (2)
C2—C1—C6—N1	176.24 (19)	N5—N4—C9—C8	59.4 (3)
C8—N1—C6—C5	84.4 (3)	N3—C8—C9—N4	−135.4 (2)
C7—N1—C6—C5	−95.4 (2)	N1—C8—C9—N4	46.4 (3)
C8—N1—C6—C1	−94.0 (2)	N4—N5—C10—N6	0.7 (2)
C7—N1—C6—C1	86.2 (2)	C11—N6—C10—N5	−0.7 (3)
N3—N2—C7—N1	2.1 (2)	C10—N6—C11—N4	0.3 (2)
N3—N2—C7—S1	−177.47 (15)	N5—N4—C11—N6	0.2 (2)
C8—N1—C7—N2	−1.7 (2)	C9—N4—C11—N6	−179.46 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N6^i	0.86	1.96	2.794 (2)	164
C1—H1A···CG1^ii	0.93	2.99	3.843 (2)	153
C4—H4A···CG2^iii	0.93	2.98	3.395 (2)	108
C5—H5B···CG1^iv	0.93	2.83	3.490 (2)	129

Symmetry codes: (i) x−1, y, z; (ii) −x+1, y−1/2, −z+1/2; (iii) x, −y+1/2, z+1/2; (iv) −x+1, y+1/2, −z+1/2.