4,4′,5,5′-Tetra­phenyl-3,3′-[methyl­idene­bis(sulfanedi­yl)]bis­(4H-1,2,4-triazole)

Zhao, B.; Liu, Z.; Gao, Y.; Song, B.; Deng, Q.

doi:10.1107/S1600536810040729

organic compounds

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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page o2814

https://doi.org/10.1107/S1600536810040729

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4,4′,5,5′-Tetraphenyl-3,3′-[methylidenebis(sulfanediyl)]bis(4H-1,2,4-triazole)

Bing Zhao,^a ^* Zhuo Liu,^a Yan Gao,^b Bo Song ^a and Qi-gang Deng ^a

^aChemistry and Chemical Engineering Institute, Qiqihar University, Heilongjiang Qiqihar 161006, People's Republic of China, and ^bSchool of Chemical Engineering, University of Science and Technology LiaoNing, Anshan 114051, People's Republic of China
^*Correspondence e-mail: zhao_submit@yahoo.com.cn

(Received 4 October 2010; accepted 11 October 2010; online 20 October 2010)

The asymmetric unit of the title compound, C₂₉H₂₂N₆S₂, contains one half-molecule situated on a twofold rotational axis. The two triazole rings form a dihedral angle of 27.6 (2)°. In the crystal, weak intermolecular C—H⋯N hydrogen bonds link the molecules into ribbons extending along [001].

Related literature

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

Experimental

Crystal data

C₂₉H₂₂N₆S₂
M_r = 518.65
Orthorhombic, P b c n
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[F² > 2σ(F²)] = 0.040
wR(F²) = 0.125
S = 1.10
2147 reflections
169 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.29 e Å⁻³

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) x, y, z+1.

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.

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810040729/cv2773Isup2.hkl

checkCIF report

Comment top

Functionalized 1,2,4-triazole derivatives received considerable attention due to their antihypertensive, antifungal and antibacterial properties (Paulvannan et al., 2001; Wahbi et al., 1995). Some crystal structures of 1H-1,2,4-triazole ring containing ether derivatives have been reported recently (Özel Güven et al., 2008a,b). Herewith we report the synthesis and crystal structure of the title compound, (I).

In (I) (Fig.1), the molecule is situated on a twofold rotational axis, so asymmetric unit contains a half of the molecule. The 1,2,4-triazole ring is planar with an r.m.s. deviation of 0.023 (2)Å and maximum deviation of 0.0037 (2)Å for atoms C8. The C8 atom shows a distorted C_sp² hybridization state with the bond angles of 110.98 (16)° (N2—C8—N3) and 126.50 (14)°(N2—C8—S1). The triazole ring and two attached phenyl rings (C1—C6 and C9—C14) form dihedral angles of 34.3 (2) and 62.2 (2)°, respectively. The dihedral angle between the two phenyl rings is 61.2 (2)°. As a result of π-π conjugation, the C_sp²-S bond length [S1—C8 = 1.7439 (2) Å] is significantly shorter than the C_sp³-S bond length [S1—C15 = 1.8092 (2) Å].

In the crystal structure, weak intermolecular C—H···N hydrogen bonds (Table 1) link the molecules into ribbons extended in direction [001].

Related literature top

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

Experimental top

A suspension of 4,5-diphenyl-4H-1,2,4-triazole-3-thiol (2.0 mmol) and 1,1-dibromomethane (1.0 mmol) in ethanol (10 ml) was stirred at room temperature. The reaction progress was monitored via TLC. The resulting precipitate was filtered off, washed with cold ethanol, dried and purified to give the target product as light yellow solid in 95% yield. Crystals of (I) suitable for single-crystal X-ray analysis were grown by slow evaporation of a solution in chloroform-ethanol (1:1).

Structure description top

In the crystal structure, weak intermolecular C—H···N hydrogen bonds (Table 1) link the molecules into ribbons extended in direction [001].

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

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 1999); cell refinement: CrystalClear (Rigaku/MSC, 1999); data reduction: CrystalClear (Rigaku/MSC, 1999); 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 (Sheldrick, 2008).

Figures top

Fig. 1. View of (I) showing the atom-labelling scheme [symmetry code: (A) -x + 1,y,-z + 1/2]. Displacement ellipsoids are drawn at the 50% probability level.

4,4',5,5'-Tetraphenyl-3,3'-[methylidenebis(sulfanediyl)]bis(4H- 1,2,4-triazole) top

Crystal data top

C₂₉H₂₂N₆S₂	F(000) = 1080
M_r = 518.65	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0826P)² + 0.5471P] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max = 0.002
2147 reflections	Δρ_max = 0.39 e Å⁻³
169 parameters	Δρ_min = −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)

Crystal data top

C₂₉H₂₂N₆S₂	V = 2453.2 (9) Å³
M_r = 518.65	Z = 4
Orthorhombic, Pbcn	Mo Kα radiation
a = 30.449 (6) Å	µ = 0.25 mm⁻¹
b = 8.2759 (17) Å	T = 113 K
c = 9.7353 (19) Å	0.22 × 0.18 × 0.12 mm

Data collection top

Rigaku Saturn CCD area-detector diffractometer	2147 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 1999)	1970 reflections with I > 2σ(I)
T_min = 0.947, T_max = 0.971	R_int = 0.045
17244 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.125	H-atom parameters constrained
S = 1.10	Δρ_max = 0.39 e Å⁻³
2147 reflections	Δρ_min = −0.29 e Å⁻³
169 parameters

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

	x	y	z	U_iso*/U_eq	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

Atomic displacement parameters (Å²) top

	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

Geometric parameters (Å, º) top

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)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

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

Symmetry code: (ii) x, y, z+1.

Experimental details

Crystal data
Chemical formula	C₂₉H₂₂N₆S₂
M_r	518.65
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	113
a, b, c (Å)	30.449 (6), 8.2759 (17), 9.7353 (19)
V (Å³)	2453.2 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.22 × 0.18 × 0.12

Data collection
Diffractometer	Rigaku Saturn CCD area-detector
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 1999)
T_min, T_max	0.947, 0.971
No. of measured, independent and observed [I > 2σ(I)] reflections	17244, 2147, 1970
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.125, 1.10
No. of reflections	2147
No. of parameters	169
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.29

Computer programs: CrystalClear (Rigaku/MSC, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···N2ⁱ	0.95	2.494	3.438 (2)	172.8

Symmetry code: (i) x, y, z+1.

Acknowledgements

We gratefully acknowledge financial support from the Science Fund for Young Scholars of Heilongjiang Province of China under grant No. QC2009C61.

References

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Volume 66| Part 11| November 2010| Page o2814

https://doi.org/10.1107/S1600536810040729

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

4,4′,5,5′-Tetra­phenyl-3,3′-[methyl­­idene­bis­(sulfanedi­yl)]bis­­(4H-1,2,4-triazole)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4,4′,5,5′-Tetraphenyl-3,3′-[methylidenebis(sulfanediyl)]bis(4H-1,2,4-triazole)