4,4',5,5'-Tetra-phenyl-3,3'-[methyl-idene-bis(sulfanedi-yl)]bis-(4H-1,2,4-triazole).

The asymmetric unit of the title compound, C(29)H(22)N(6)S(2), contains one half-mol-ecule situated on a twofold rotational axis. The two triazole rings form a dihedral angle of 27.6 (2)°. In the crystal, weak inter-molecular C-H⋯N hydrogen bonds link the mol-ecules into ribbons extending along [001].

Related literature

For related structures, see: Özel Güven et al. (2008 ▶). For the pharmacological properties of triazole derivatives, see: Paulvannan et al. (2001 ▶); Wahbi et al. (1995 ▶).

Experimental

Crystal data

C29H22N6S2

M = 518.65

Orthorhombic,

a = 30.449 (6) Å

b = 8.2759 (17) Å

c = 9.7353 (19) Å

V = 2453.2 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 113 K

0.22 × 0.18 × 0.12 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 1999 ▶) T min = 0.947, T max = 0.971

17244 measured reflections

2147 independent reflections

1970 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.125

S = 1.10

2147 reflections

169 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.29 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 1999 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810040729/cv2773sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810040729/cv2773Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C29H22N6S2	F(000) = 1080
Mr = 518.65	Dx = 1.404 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 6468 reflections
a = 30.449 (6) Å	θ = 1.3–27.9°
b = 8.2759 (17) Å	µ = 0.25 mm−1
c = 9.7353 (19) Å	T = 113 K
V = 2453.2 (9) Å3	Prism, colorless
Z = 4	0.22 × 0.18 × 0.12 mm

Rigaku Saturn CCD area-detector diffractometer	2147 independent reflections
Radiation source: rotating anode	1970 reflections with I > 2σ(I)
confocal	Rint = 0.045
Detector resolution: 7.31 pixels mm-1	θmax = 25.0°, θmin = 1.3°
φ and ω scans	h = −36→36
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 1999)	k = −9→9
Tmin = 0.947, Tmax = 0.971	l = −11→10
17244 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040	H-atom parameters constrained
wR(F2) = 0.125	w = 1/[σ2(Fo2) + (0.0826P)2 + 0.5471P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max = 0.002
2147 reflections	Δρmax = 0.39 e Å−3
169 parameters	Δρmin = −0.29 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.050 (4)

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.484576 (14)	0.18721 (6)	0.40035 (4)	0.0246 (2)
N1	0.37084 (5)	0.2686 (2)	0.23508 (15)	0.0243 (4)
N2	0.41528 (5)	0.23130 (19)	0.22557 (15)	0.0244 (4)
N3	0.39880 (5)	0.27134 (18)	0.44399 (15)	0.0185 (4)
C1	0.28189 (6)	0.2592 (2)	0.34631 (19)	0.0254 (4)
H1	0.2872	0.1913	0.2694	0.030*
C2	0.23919 (6)	0.2897 (3)	0.3878 (2)	0.0288 (5)
H2	0.2153	0.2438	0.3388	0.035*
C3	0.23142 (6)	0.3863 (3)	0.49991 (19)	0.0299 (5)
H3	0.2021	0.4061	0.5291	0.036*
C4	0.26622 (7)	0.4548 (2)	0.5704 (2)	0.0302 (5)
H4	0.2606	0.5211	0.6481	0.036*
C5	0.30922 (6)	0.4281 (2)	0.52912 (18)	0.0260 (4)
H5	0.3329	0.4775	0.5768	0.031*
C6	0.31729 (6)	0.3280 (2)	0.41710 (18)	0.0207 (4)
C7	0.36147 (6)	0.2918 (2)	0.36533 (19)	0.0203 (4)
C8	0.43093 (6)	0.2328 (2)	0.35103 (18)	0.0207 (4)
C9	0.40330 (6)	0.2658 (2)	0.59099 (17)	0.0190 (4)
C10	0.37948 (6)	0.1537 (2)	0.66540 (18)	0.0251 (4)
H10	0.3601	0.0812	0.6200	0.030*
C11	0.38411 (6)	0.1481 (3)	0.80686 (19)	0.0291 (5)
H11	0.3673	0.0734	0.8590	0.035*
C12	0.41327 (7)	0.2513 (3)	0.87285 (19)	0.0298 (5)
H12	0.4167	0.2464	0.9698	0.036*
C13	0.43734 (6)	0.3613 (2)	0.79676 (19)	0.0297 (5)
H13	0.4576	0.4310	0.8417	0.036*
C14	0.43218 (6)	0.3708 (2)	0.65523 (18)	0.0240 (4)
H14	0.4482	0.4482	0.6033	0.029*
C15	0.5000	0.0719 (3)	0.2500	0.0245 (6)
H15A	0.4751	0.0011	0.2250	0.029*	0.50
H15B	0.5249	0.0011	0.2750	0.029*	0.50

	U11	U22	U33	U12	U13	U23
S1	0.0196 (3)	0.0371 (4)	0.0171 (3)	0.00410 (18)	−0.00078 (16)	−0.00138 (18)
N1	0.0225 (8)	0.0335 (9)	0.0168 (8)	0.0024 (6)	−0.0003 (6)	0.0006 (6)
N2	0.0226 (8)	0.0324 (9)	0.0181 (8)	0.0017 (7)	0.0001 (6)	0.0006 (6)
N3	0.0188 (8)	0.0224 (8)	0.0143 (8)	0.0001 (6)	−0.0011 (6)	0.0003 (6)
C1	0.0261 (10)	0.0308 (10)	0.0193 (10)	0.0008 (8)	−0.0022 (7)	0.0001 (8)
C2	0.0223 (10)	0.0385 (12)	0.0256 (11)	−0.0025 (8)	−0.0010 (7)	0.0084 (8)
C3	0.0244 (9)	0.0360 (12)	0.0292 (10)	0.0067 (8)	0.0054 (8)	0.0100 (9)
C4	0.0344 (10)	0.0294 (11)	0.0267 (10)	0.0083 (8)	0.0062 (8)	0.0002 (9)
C5	0.0286 (9)	0.0269 (10)	0.0224 (10)	0.0026 (8)	−0.0009 (8)	0.0000 (8)
C6	0.0221 (9)	0.0232 (10)	0.0169 (9)	0.0026 (7)	−0.0001 (7)	0.0045 (7)
C7	0.0201 (9)	0.0231 (9)	0.0176 (9)	0.0004 (7)	−0.0023 (7)	0.0008 (7)
C8	0.0223 (9)	0.0248 (9)	0.0152 (9)	0.0005 (7)	0.0010 (7)	0.0002 (7)
C9	0.0205 (9)	0.0240 (10)	0.0125 (9)	0.0044 (7)	−0.0008 (7)	0.0008 (7)
C10	0.0259 (9)	0.0293 (10)	0.0203 (10)	−0.0010 (8)	−0.0008 (7)	0.0007 (8)
C11	0.0305 (10)	0.0361 (11)	0.0207 (9)	0.0039 (9)	0.0058 (8)	0.0070 (8)
C12	0.0348 (11)	0.0417 (12)	0.0130 (9)	0.0129 (9)	−0.0014 (8)	−0.0001 (8)
C13	0.0317 (10)	0.0355 (11)	0.0218 (9)	0.0040 (9)	−0.0063 (8)	−0.0089 (8)
C14	0.0253 (9)	0.0265 (10)	0.0201 (9)	0.0007 (7)	−0.0014 (7)	−0.0014 (8)
C15	0.0228 (12)	0.0283 (14)	0.0224 (13)	0.000	0.0048 (10)	0.000

S1—C8	1.7439 (19)	C5—C6	1.391 (3)
S1—C15	1.8092 (15)	C5—H5	0.9500
N1—C7	1.314 (2)	C6—C7	1.467 (3)
N1—N2	1.391 (2)	C9—C10	1.382 (3)
N2—C8	1.311 (2)	C9—C14	1.386 (3)
N3—C8	1.370 (2)	C10—C11	1.385 (3)
N3—C7	1.381 (2)	C10—H10	0.9500
N3—C9	1.438 (2)	C11—C12	1.389 (3)
C1—C2	1.385 (3)	C11—H11	0.9500
C1—C6	1.400 (3)	C12—C13	1.384 (3)
C1—H1	0.9500	C12—H12	0.9500
C2—C3	1.373 (3)	C13—C14	1.389 (3)
C2—H2	0.9500	C13—H13	0.9500
C3—C4	1.384 (3)	C14—H14	0.9500
C3—H3	0.9500	C15—S1i	1.8092 (15)
C4—C5	1.387 (3)	C15—H15A	0.9900
C4—H4	0.9500	C15—H15B	0.9900
C8—S1—C15	97.73 (6)	N2—C8—N3	110.98 (16)
C7—N1—N2	107.93 (14)	N2—C8—S1	126.50 (14)
C8—N2—N1	106.82 (14)	N3—C8—S1	122.50 (13)
C8—N3—C7	104.47 (15)	C10—C9—C14	121.16 (17)
C8—N3—C9	125.57 (15)	C10—C9—N3	119.54 (16)
C7—N3—C9	129.35 (15)	C14—C9—N3	119.29 (16)
C2—C1—C6	120.33 (19)	C9—C10—C11	119.34 (18)
C2—C1—H1	119.8	C9—C10—H10	120.3
C6—C1—H1	119.8	C11—C10—H10	120.3
C3—C2—C1	119.98 (19)	C10—C11—C12	120.29 (18)
C3—C2—H2	120.0	C10—C11—H11	119.9
C1—C2—H2	120.0	C12—C11—H11	119.9
C2—C3—C4	120.05 (18)	C13—C12—C11	119.70 (18)
C2—C3—H3	120.0	C13—C12—H12	120.2
C4—C3—H3	120.0	C11—C12—H12	120.2
C3—C4—C5	120.90 (19)	C12—C13—C14	120.54 (18)
C3—C4—H4	119.5	C12—C13—H13	119.7
C5—C4—H4	119.5	C14—C13—H13	119.7
C4—C5—C6	119.26 (18)	C9—C14—C13	118.94 (18)
C4—C5—H5	120.4	C9—C14—H14	120.5
C6—C5—H5	120.4	C13—C14—H14	120.5
C5—C6—C1	119.46 (17)	S1—C15—S1i	116.36 (15)
C5—C6—C7	123.54 (17)	S1—C15—H15A	108.2
C1—C6—C7	116.99 (17)	S1i—C15—H15A	108.2
N1—C7—N3	109.79 (16)	S1—C15—H15B	108.2
N1—C7—C6	124.08 (16)	S1i—C15—H15B	108.2
N3—C7—C6	126.09 (16)	H15A—C15—H15B	107.4
C7—N1—N2—C8	0.3 (2)	N1—N2—C8—S1	177.52 (14)
C6—C1—C2—C3	−0.7 (3)	C7—N3—C8—N2	0.7 (2)
C1—C2—C3—C4	0.8 (3)	C9—N3—C8—N2	172.43 (17)
C2—C3—C4—C5	0.3 (3)	C7—N3—C8—S1	−177.52 (13)
C3—C4—C5—C6	−1.4 (3)	C9—N3—C8—S1	−5.8 (3)
C4—C5—C6—C1	1.4 (3)	C15—S1—C8—N2	−20.82 (19)
C4—C5—C6—C7	−179.98 (17)	C15—S1—C8—N3	157.12 (16)
C2—C1—C6—C5	−0.4 (3)	C8—N3—C9—C10	−113.1 (2)
C2—C1—C6—C7	−179.05 (17)	C7—N3—C9—C10	56.5 (3)
N2—N1—C7—N3	0.2 (2)	C8—N3—C9—C14	65.6 (2)
N2—N1—C7—C6	−177.72 (17)	C7—N3—C9—C14	−124.8 (2)
C8—N3—C7—N1	−0.5 (2)	C14—C9—C10—C11	1.0 (3)
C9—N3—C7—N1	−171.81 (16)	N3—C9—C10—C11	179.62 (16)
C8—N3—C7—C6	177.31 (17)	C9—C10—C11—C12	−1.7 (3)
C9—N3—C7—C6	6.0 (3)	C10—C11—C12—C13	0.8 (3)
C5—C6—C7—N1	−146.00 (19)	C11—C12—C13—C14	0.8 (3)
C1—C6—C7—N1	32.6 (3)	C10—C9—C14—C13	0.6 (3)
C5—C6—C7—N3	36.5 (3)	N3—C9—C14—C13	−178.03 (16)
C1—C6—C7—N3	−144.92 (18)	C12—C13—C14—C9	−1.5 (3)
N1—N2—C8—N3	−0.6 (2)	C8—S1—C15—S1i	80.05 (6)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···N2ii	0.95	2.49	3.438 (2)	173

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯N2i	0.95	2.49	3.438 (2)	173

Symmetry code: (i) .