3-Phen­oxy­methyl-6-phenyl-1,2,4-triazolo[3,4-b][1,3,4]thia­diazole

Mohamed, S.K.; Mague, J.T.; Akkurt, M.; Bakhite, E.A.; Albayati, M.R.

doi:10.1107/S241431461600626X

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 4| April 2016| x160626

doi:10.1107/S241431461600626X

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3-Phenoxymethyl-6-phenyl-1,2,4-triazolo[3,4-b][1,3,4]thiadiazole

Shaaban K. Mohamed,^a,^b Joel T. Mague,^c Mehmet Akkurt,^d Etify A. Bakhite ^e and Mustafa R. Albayati ^f ^*

^aChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, ^bChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, ^cDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, ^dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^eChemistry Department, Faculty of Science, Assiut University, 71516 Assiut, Egypt, and ^fKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
^*Correspondence e-mail: shaabankamel@yahoo.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 9 April 2016; accepted 14 April 2016; online 26 April 2016)

In the title compound, C₁₆H₁₂N₄OS, the bicyclic triazolothiadiazole core is approximately planar, with an r.m.s. deviation of 0.018 Å. The phenyl rings are inclined to its mean plane by 7.66 (7) and 71.79 (7)°. In the crystal, molecules are linked via a C—H⋯π interaction and a π–π interaction [intercentroid distance = 3.2942 (9) Å] involving inversion-related triazole rings. These interactions result in the formation of chains propagating along [10-1].

Keywords: crystal structure; N-bridged heterocycles; triazolo thiadiazoles; triazoles; thiadiazoles; C—H⋯π interactions; π–π interactions.

CCDC reference: 1473995

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Chemical scheme

Structure description

N-Bridged heterocycles derived from 1,2,4-triazoles have applications in medicine, agriculture and industry (Farghaly et al., 2006 ). Heterocycles bearing a triazole or 1,3,4-thiadiazole moiety are reported to show a wide spectrum of biological activity (Suresh Kumar et al., 2010 ; Mallikarjuna et al., 2009 ) such as anti-bacterial (Abdel-Rahman & Farghaly, 2004 ), anti-aggregator agents (Czarnocka-Janowicz et al., 1991 ), anti-viral (Srivastava et al., 1991 ) and anti-inflammatory (Unangst et al., 1992 ) activities. Triazolothiadiazoles in particular are reported to possess anti-bacterial, antifungal, CNS depressant, anti-viral, analgesic, anti-tuberculosis and plant-growth regulatory effects (Abdallah et al., 2005 ; El-Khawass & Habib 1989 ; Mishra, 1987 ; Shiradkar & Kale, 2006 ). Based on such facts, we report herein on the synthesis and crystal structure of the title compound.

In the title molecule, (Fig. 1), the bicyclic triazolothiadiazole core is approximately planar with an r.m.s. deviation of 0.018 Å and a maximum deviation of 0.021 (1) Å for atom N2. The phenyl rings, C2–C7 and C11–C16, are inclined to its mean plane by 7.66 (7) and 71.79 (7)°, respectively.

Figure 1
The molecular structure of the title compound, showing the atom labeling and 50% probability displacement ellipsoids.

In the crystal, molecules are linked via a C—H⋯π interaction (Fig. 2 and Table 1) and by π–π interactions between triazole rings [Cg2⋯Cg2ⁱ = 3.2942 (9) Å, Cg2 is the centroid of ring N2–N4/C8/C9, symmetry code (i): − x + 1, − y + 1, − z + 2]; see Fig. 3. These interactions result in the formation of chains propagating along [10 $[\overline{1}]$ ].

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C11–C16 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯Cgⁱ	0.95	2.79	3.633 (2)	148
Symmetry code: (i) -x, -y+1, -z+1.

Figure 2
The crystal packing of the title compound, viewed along the a axis. H atoms have been omitted for clarity.

Figure 3
Details of the offset π-stacking in the crystal of the title compound.

Synthesis and crystallization

A mixture of 4-amino-3-phenoxymethyl-1,2,4-triazoline-5-thione (2.22 g, 0.01 mol) and benzoic acid (1.22 g, 0.01 mol) in phosphorus oxychloride (20 ml) was heated under reflux on a steam bath for 4 h and then left to cool. The reaction mixture was poured portionwise into ice–water (50 ml) with stirring and allowed to stand at room temperature for 2 h. The solid that formed was collected by filtration and crystallized from ethanol as colorless plates (yield: 82%; m.p.: 482–483 K). IR: 1600 cm⁻¹ (C=N). ¹H NMR (CDCl₃): δ 6.7–7.5 (m, 10 H, Ar—H), δ 5.0 (s, 2H, OCH₂).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₆H₁₂N₄OS
M_r	308.36
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	5.9850 (3), 21.0709 (10), 11.5617 (5)
β (°)	100.423 (2)
V (Å³)	1433.98 (12)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	2.07
Crystal size (mm)	0.30 × 0.16 × 0.02

Data collection
Diffractometer	Bruker D8 VENTURE PHOTON 100 CMOS
Absorption correction	Multi-scan (SADABS; Bruker, 2016 )
T_min, T_max	0.79, 0.97
No. of measured, independent and observed [I > 2σ(I)] reflections	10736, 2799, 2464
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.619

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.089, 1.03
No. of reflections	2799
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.30
Computer programs: APEX3 and SAINT (Bruker, 2016), SHELXT (Sheldrick, 2015a ), SHELXL2014 (Sheldrick, 2015b ), DIAMOND (Brandenburg & Putz, 2012 ) and SHELXTL (Sheldrick, 2008 ).

Structural data

CCDC reference: 1473995

Crystal structure: contains datablocks global, I. DOI: 10.1107/S241431461600626X/su4033sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S241431461600626X/su4033Isup2.hkl

Supporting information file. DOI: 10.1107/S241431461600626X/su4033Isup3.cml

checkCIF report

Experimental top

A mixture of 4-amino-3-phenoxymethyl-1,2,4-triazoline-5-thione (2.22 g, 0.01 mol) and benzoic acid (1.22 g, 0.01 mol) in phosphorus oxychloride (20 ml) was heated under reflux on a steam bath for 4 h and then left to cool. The reaction mixture was poured portionwise into ice–water (50 ml) with stirring and allowed to stand at room temperature for 2 h. The solid that formed was collected by filtration and crystallized from ethanol as colorless plates (yield: 82%; m.p.: 482–483 K). IR: 1600 cm^-1 (C═N). ¹H NMR (CDCl₃): δ 6.7–7.5 (m, 10 H, Ar—H), δ 5.0 (s, 2H, OCH₂).

Structure description top

N-Bridged heterocycles derived from 1,2,4-triazoles have applications in medicine, agriculture and industry (Farghaly et al., 2006). Heterocycles bearing a triazole or 1,3,4-thiadiazole moiety are reported to show a wide spectrum of biological activity (Suresh Kumar et al., 2010; Mallikarjuna et al., 2009) such as anti-bacterial (Abdel-Rahman & Farghaly, 2004), anti-aggregator agents (Czarnocka-Janowicz et al., 1991), anti-viral (Srivastava et al., 1991) and anti-inflammatory (Unangst et al., 1992) activities. Triazolothiadiazoles in particular are reported to possess anti-bacterial, antifungal, CNS depressant, anti-viral, analgesic, anti-tuberculosis and plant-growth regulatory effects (Abdallah et al., 2005; El-Khawass & Habib 1989; Mishra, 1987; Shiradkar & Kale, 2006). Based on such facts, we report herein on the synthesis and crystal structure of the title compound.

In the crystal, molecules are linked via a C—H···π interaction (Fig. 2 and Table 1) and by π–π interactions between triazole rings [Cg2···Cg2ⁱ = 3.2942 (9) Å, Cg2 is the centroid of ring N2–N4/C8/C9, symmetry code (i): - x + 1, - y + 1, - z + 2]; see Fig. 3. These interactions result in the formation of chains propagating along [101].

Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom labeling and 50% probability displacement ellipsoids.
	Fig. 2. The crystal packing of the title compound, viewed along the a axis. H atoms have been omitted for clarity.
	Fig. 3. Details of the offset π-stacking in the crystal of the title compound.

3-Phenoxymethyl-6-phenyl-1,2,4-triazolo[3,4-b][1,3,4]thiadiazole top

Crystal data top

C₁₆H₁₂N₄OS	F(000) = 640
M_r = 308.36	D_x = 1.428 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
a = 5.9850 (3) Å	Cell parameters from 7818 reflections
b = 21.0709 (10) Å	θ = 4.2–72.5°
c = 11.5617 (5) Å	µ = 2.07 mm⁻¹
β = 100.423 (2)°	T = 150 K
V = 1433.98 (12) Å³	Plate, colourless
Z = 4	0.30 × 0.16 × 0.02 mm

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	2799 independent reflections
Radiation source: INCOATEC IµS micro–focus source	2464 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.038
Detector resolution: 10.4167 pixels mm^-1	θ_max = 72.5°, θ_min = 4.2°
ω scans	h = −7→6
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −22→25
T_min = 0.79, T_max = 0.97	l = −14→14
10736 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.089	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0407P)² + 0.5423P] where P = (F_o² + 2F_c²)/3
2799 reflections	(Δ/σ)_max = 0.002
199 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₆H₁₂N₄OS	V = 1433.98 (12) Å³
M_r = 308.36	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 5.9850 (3) Å	µ = 2.07 mm⁻¹
b = 21.0709 (10) Å	T = 150 K
c = 11.5617 (5) Å	0.30 × 0.16 × 0.02 mm
β = 100.423 (2)°

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	2799 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2016)	2464 reflections with I > 2σ(I)
T_min = 0.79, T_max = 0.97	R_int = 0.038
10736 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.089	H-atom parameters constrained
S = 1.03	Δρ_max = 0.20 e Å⁻³
2799 reflections	Δρ_min = −0.30 e Å⁻³
199 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 - 0.99 Å) and included as riding contributions with isotropic displacement parameters 1.2 times those of the attached atoms.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.80639 (6)	0.53901 (2)	0.80341 (3)	0.03014 (13)
O1	0.27388 (19)	0.32989 (6)	0.83039 (10)	0.0355 (3)
N1	0.4069 (2)	0.48387 (6)	0.74636 (11)	0.0293 (3)
N2	0.5213 (2)	0.45919 (6)	0.85076 (11)	0.0273 (3)
N3	0.8120 (2)	0.45577 (6)	0.99887 (12)	0.0315 (3)
N4	0.6450 (2)	0.41284 (6)	1.01880 (12)	0.0327 (3)
C1	0.5389 (3)	0.52624 (7)	0.71208 (14)	0.0286 (3)
C2	0.4730 (3)	0.56291 (8)	0.60310 (13)	0.0308 (3)
C3	0.6286 (3)	0.60294 (9)	0.56407 (15)	0.0378 (4)
H3	0.7784	0.6067	0.6079	0.045*
C4	0.5652 (4)	0.63750 (10)	0.46100 (17)	0.0454 (5)
H4	0.6722	0.6645	0.4341	0.055*
C5	0.3467 (4)	0.63270 (10)	0.39754 (16)	0.0473 (5)
H5	0.3035	0.6566	0.3274	0.057*
C6	0.1908 (3)	0.59298 (10)	0.43620 (16)	0.0452 (5)
H6	0.0409	0.5896	0.3922	0.054*
C7	0.2524 (3)	0.55821 (9)	0.53848 (15)	0.0374 (4)
H7	0.1448	0.5312	0.5648	0.045*
C8	0.7310 (2)	0.48242 (7)	0.89660 (14)	0.0280 (3)
C9	0.4735 (3)	0.41535 (7)	0.92963 (14)	0.0295 (3)
C10	0.2645 (3)	0.37680 (8)	0.91792 (15)	0.0331 (4)
H10A	0.2545	0.3563	0.9939	0.040*
H10B	0.1290	0.4040	0.8946	0.040*
C11	0.1005 (3)	0.28603 (7)	0.81265 (13)	0.0279 (3)
C12	−0.0781 (3)	0.28504 (8)	0.87418 (14)	0.0336 (4)
H12	−0.0861	0.3155	0.9339	0.040*
C13	−0.2456 (3)	0.23880 (9)	0.84714 (15)	0.0393 (4)
H13	−0.3679	0.2376	0.8893	0.047*
C14	−0.2361 (3)	0.19474 (8)	0.75990 (15)	0.0386 (4)
H14	−0.3520	0.1636	0.7415	0.046*
C15	−0.0568 (3)	0.19615 (8)	0.69943 (15)	0.0360 (4)
H15	−0.0500	0.1659	0.6392	0.043*
C16	0.1130 (3)	0.24126 (8)	0.72580 (14)	0.0329 (4)
H16	0.2371	0.2416	0.6849	0.040*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0238 (2)	0.0329 (2)	0.0308 (2)	−0.00024 (14)	−0.00293 (15)	−0.00098 (15)
O1	0.0313 (6)	0.0377 (6)	0.0394 (6)	−0.0097 (5)	0.0120 (5)	−0.0135 (5)
N1	0.0244 (6)	0.0340 (7)	0.0268 (6)	0.0049 (5)	−0.0031 (5)	−0.0046 (5)
N2	0.0220 (6)	0.0283 (7)	0.0291 (6)	0.0018 (5)	−0.0021 (5)	−0.0039 (5)
N3	0.0264 (6)	0.0317 (7)	0.0336 (7)	0.0007 (5)	−0.0019 (5)	−0.0008 (5)
N4	0.0300 (7)	0.0314 (7)	0.0348 (7)	0.0016 (5)	0.0007 (6)	−0.0020 (6)
C1	0.0246 (7)	0.0306 (8)	0.0289 (8)	0.0052 (6)	0.0001 (6)	−0.0071 (6)
C2	0.0308 (8)	0.0325 (8)	0.0275 (7)	0.0081 (6)	0.0008 (6)	−0.0058 (6)
C3	0.0334 (9)	0.0454 (10)	0.0335 (8)	0.0064 (7)	0.0029 (7)	0.0003 (7)
C4	0.0489 (11)	0.0502 (11)	0.0383 (10)	0.0095 (8)	0.0109 (8)	0.0069 (8)
C5	0.0556 (12)	0.0530 (12)	0.0311 (9)	0.0208 (9)	0.0022 (8)	0.0039 (8)
C6	0.0422 (10)	0.0549 (12)	0.0331 (9)	0.0162 (9)	−0.0074 (8)	−0.0048 (8)
C7	0.0328 (9)	0.0428 (10)	0.0328 (8)	0.0072 (7)	−0.0041 (7)	−0.0058 (7)
C8	0.0221 (7)	0.0284 (8)	0.0312 (8)	0.0018 (6)	−0.0014 (6)	−0.0052 (6)
C9	0.0275 (8)	0.0284 (8)	0.0313 (8)	0.0027 (6)	0.0024 (6)	−0.0044 (6)
C10	0.0302 (8)	0.0344 (9)	0.0348 (8)	−0.0028 (6)	0.0063 (7)	−0.0091 (7)
C11	0.0257 (7)	0.0299 (8)	0.0272 (7)	−0.0027 (6)	0.0021 (6)	0.0013 (6)
C12	0.0321 (8)	0.0407 (9)	0.0283 (8)	−0.0030 (7)	0.0063 (6)	−0.0024 (7)
C13	0.0334 (9)	0.0485 (11)	0.0370 (9)	−0.0086 (7)	0.0090 (7)	0.0062 (8)
C14	0.0396 (9)	0.0360 (9)	0.0379 (9)	−0.0111 (7)	0.0010 (7)	0.0048 (7)
C15	0.0429 (9)	0.0303 (9)	0.0326 (8)	−0.0037 (7)	0.0014 (7)	−0.0017 (7)
C16	0.0343 (9)	0.0346 (9)	0.0308 (8)	−0.0031 (7)	0.0081 (7)	−0.0025 (6)

Geometric parameters (Å, º) top

S1—C8	1.7210 (17)	C5—H5	0.9500
S1—C1	1.7716 (15)	C6—C7	1.383 (3)
O1—C11	1.3772 (18)	C6—H6	0.9500
O1—C10	1.4229 (19)	C7—H7	0.9500
N1—C1	1.301 (2)	C9—C10	1.477 (2)
N1—N2	1.3772 (18)	C10—H10A	0.9900
N2—C8	1.362 (2)	C10—H10B	0.9900
N2—C9	1.364 (2)	C11—C12	1.387 (2)
N3—C8	1.320 (2)	C11—C16	1.390 (2)
N3—N4	1.3976 (19)	C12—C13	1.392 (2)
N4—C9	1.318 (2)	C12—H12	0.9500
C1—C2	1.470 (2)	C13—C14	1.379 (3)
C2—C3	1.391 (3)	C13—H13	0.9500
C2—C7	1.398 (2)	C14—C15	1.383 (3)
C3—C4	1.390 (3)	C14—H14	0.9500
C3—H3	0.9500	C15—C16	1.385 (2)
C4—C5	1.382 (3)	C15—H15	0.9500
C4—H4	0.9500	C16—H16	0.9500
C5—C6	1.387 (3)

C8—S1—C1	87.53 (7)	N3—C8—S1	139.50 (12)
C11—O1—C10	116.52 (12)	N2—C8—S1	109.45 (11)
C1—N1—N2	107.06 (12)	N4—C9—N2	108.78 (14)
C8—N2—C9	105.86 (13)	N4—C9—C10	125.22 (15)
C8—N2—N1	118.82 (13)	N2—C9—C10	125.99 (14)
C9—N2—N1	135.27 (13)	O1—C10—C9	107.79 (13)
C8—N3—N4	105.39 (13)	O1—C10—H10A	110.1
C9—N4—N3	108.93 (13)	C9—C10—H10A	110.1
N1—C1—C2	122.58 (14)	O1—C10—H10B	110.1
N1—C1—S1	117.12 (12)	C9—C10—H10B	110.1
C2—C1—S1	120.30 (12)	H10A—C10—H10B	108.5
C3—C2—C7	119.53 (16)	O1—C11—C12	124.31 (14)
C3—C2—C1	120.35 (15)	O1—C11—C16	115.17 (14)
C7—C2—C1	120.12 (16)	C12—C11—C16	120.52 (15)
C4—C3—C2	120.06 (17)	C11—C12—C13	119.05 (16)
C4—C3—H3	120.0	C11—C12—H12	120.5
C2—C3—H3	120.0	C13—C12—H12	120.5
C5—C4—C3	120.15 (19)	C14—C13—C12	120.80 (16)
C5—C4—H4	119.9	C14—C13—H13	119.6
C3—C4—H4	119.9	C12—C13—H13	119.6
C4—C5—C6	120.02 (17)	C13—C14—C15	119.57 (16)
C4—C5—H5	120.0	C13—C14—H14	120.2
C6—C5—H5	120.0	C15—C14—H14	120.2
C7—C6—C5	120.29 (18)	C14—C15—C16	120.60 (16)
C7—C6—H6	119.9	C14—C15—H15	119.7
C5—C6—H6	119.9	C16—C15—H15	119.7
C6—C7—C2	119.95 (18)	C15—C16—C11	119.45 (16)
C6—C7—H7	120.0	C15—C16—H16	120.3
C2—C7—H7	120.0	C11—C16—H16	120.3
N3—C8—N2	111.04 (14)

C1—N1—N2—C8	1.29 (18)	C9—N2—C8—S1	−179.52 (10)
C1—N1—N2—C9	178.30 (16)	N1—N2—C8—S1	−1.71 (17)
C8—N3—N4—C9	−0.08 (17)	C1—S1—C8—N3	−177.26 (19)
N2—N1—C1—C2	−179.93 (13)	C1—S1—C8—N2	1.16 (11)
N2—N1—C1—S1	−0.27 (16)	N3—N4—C9—N2	−0.30 (17)
C8—S1—C1—N1	−0.54 (13)	N3—N4—C9—C10	179.72 (14)
C8—S1—C1—C2	179.13 (13)	C8—N2—C9—N4	0.55 (17)
N1—C1—C2—C3	−173.41 (15)	N1—N2—C9—N4	−176.72 (15)
S1—C1—C2—C3	6.9 (2)	C8—N2—C9—C10	−179.47 (15)
N1—C1—C2—C7	7.2 (2)	N1—N2—C9—C10	3.3 (3)
S1—C1—C2—C7	−172.46 (12)	C11—O1—C10—C9	175.43 (13)
C7—C2—C3—C4	−0.6 (3)	N4—C9—C10—O1	−106.96 (18)
C1—C2—C3—C4	−179.97 (16)	N2—C9—C10—O1	73.1 (2)
C2—C3—C4—C5	0.6 (3)	C10—O1—C11—C12	−0.2 (2)
C3—C4—C5—C6	−0.5 (3)	C10—O1—C11—C16	179.35 (14)
C4—C5—C6—C7	0.3 (3)	O1—C11—C12—C13	179.05 (15)
C5—C6—C7—C2	−0.2 (3)	C16—C11—C12—C13	−0.4 (2)
C3—C2—C7—C6	0.4 (2)	C11—C12—C13—C14	−0.5 (3)
C1—C2—C7—C6	179.76 (15)	C12—C13—C14—C15	0.7 (3)
N4—N3—C8—N2	0.43 (17)	C13—C14—C15—C16	0.1 (3)
N4—N3—C8—S1	178.84 (15)	C14—C15—C16—C11	−1.0 (3)
C9—N2—C8—N3	−0.62 (17)	O1—C11—C16—C15	−178.35 (14)
N1—N2—C8—N3	177.19 (12)	C12—C11—C16—C15	1.2 (2)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C11–C16 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···Cgⁱ	0.95	2.79	3.633 (2)	148

Symmetry code: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C11–C16 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···Cgⁱ	0.95	2.79	3.633 (2)	148

Symmetry code: (i) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₂N₄OS
M_r	308.36
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	5.9850 (3), 21.0709 (10), 11.5617 (5)
β (°)	100.423 (2)
V (Å³)	1433.98 (12)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	2.07
Crystal size (mm)	0.30 × 0.16 × 0.02

Data collection
Diffractometer	Bruker D8 VENTURE PHOTON 100 CMOS
Absorption correction	Multi-scan (SADABS; Bruker, 2016)
T_min, T_max	0.79, 0.97
No. of measured, independent and observed [I > 2σ(I)] reflections	10736, 2799, 2464
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.619

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.089, 1.03
No. of reflections	2799
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.30

Computer programs: APEX3 (Bruker, 2016), SAINT (Bruker, 2016), SAINT (Bruker, 2016), SHELXT (Sheldrick, 2015a), SHELXL2014 (Sheldrick, 2015b), DIAMOND (Brandenburg & Putz, 2012), SHELXTL (Sheldrick, 2008).

Acknowledgements

The support of NSF–MRI Grant No. 1228232 for the purchase of the diffractometer and Tulane University for support of the Tulane Crystallography Laboratory are gratefully acknowledged.

References

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Volume 1| Part 4| April 2016| x160626

doi:10.1107/S241431461600626X

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

3-Phen­­oxy­methyl-6-phenyl-1,2,4-triazolo[3,4-b][1,3,4]thia­diazole

Structure description

Synthesis and crystallization

Refinement

Structural data

Acknowledgements

References

organic compounds

3-Phenoxymethyl-6-phenyl-1,2,4-triazolo[3,4-b][1,3,4]thiadiazole