3,3′-Bis(2-thienylmeth­yl)-4,4′-(butane-1,4-di­yl)bis­(4,5-dihydro-1H-1,2,4-triazol-5-one)

Ünver, Y.; Ustabaş, R.; Çoruh, U.; Sancak, K.; Vázquez-López, E.M.

doi:10.1107/S1600536806031898

3,3′-Bis(2-thienylmethyl)-4,4′-(butane-1,4-diyl)bis(4,5-dihydro-1H-1,2,4-triazol-5-one)

Y. Ünver, R. Ustabaş, U. Çoruh, K. Sancak and E. M. Vázquez-López

The title compound, C₁₈H₂₀N₆O₂S₂, has a centre of symmetry. The thiophene ring makes an angle of 70.58 (6)° with the triazole ring. Molecules are linked via N—H

O hydrogen bonds, forming a three-dimensional network.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806031898/ob2045sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806031898/ob2045Isup2.hkl Contains datablock I

CCDC reference: 621450

checkCIF report

Key indicators

Single-crystal X-ray study
T = 173 K
Mean (C-C)= 0.003 Å
R factor = 0.043
wR factor = 0.102
Data-to-parameter ratio = 17.1

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No errors found in this datablock

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

3,3'-Bis(2-thienylmethyl)4,4'-(butane-1,4-diyl)bis(4,5-dihydro-1H- 1,2,4-triazol-5-one) top

Crystal data top

C₁₈H₂₀N₆O₂S₂	F(000) = 436
M_r = 416.54	D_x = 1.470 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 528–529 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 9.6148 (15) Å	Cell parameters from 1491 reflections
b = 7.2699 (11) Å	θ = 2.1–28.0°
c = 13.523 (2) Å	µ = 0.31 mm⁻¹
β = 95.289 (3)°	T = 173 K
V = 941.2 (2) Å³	Prism, colourless
Z = 2	0.30 × 0.22 × 0.13 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	1491 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.061
Graphite monochromator	θ_max = 28.0°, θ_min = 2.1°
φ and ω scans	h = −12→11
5511 measured reflections	k = −9→7
2175 independent reflections	l = −17→17

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.102	H-atom parameters constrained
S = 0.92	w = 1/[σ²(F_o²) + (0.0482P)²] where P = (F_o² + 2F_c²)/3
2175 reflections	(Δ/σ)_max = 0.001
127 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Special details top

Experimental. IR (KBr, ν, cm-1): 3188 (NH), 1701 (C?O), 1577 (C=N). 1H NMR (DMSO-d6): δ 1.21 (bs, 2CH2), 3.40 (bs, 2NCH2), 4.13 (4H, 2CH2, thiophen), 6.93–7.42 (m, 6H, 6CH ABC system, for two thiophen ring), 11.58 (2H, s, 2NH). 13 C NMR (DMSO-d6): δ 25.21 (CH2), 26.08 (thiophen-CH2), 40.21 (–NCH2), 126.92, 126.49, 126.92 (thiophen CH), 137.56 (thiophen C), 145.59 (triazole C-3), 154.87 (triazole C-5).

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
C1	0.5265 (2)	1.3863 (3)	0.34486 (18)	0.0391 (6)
H1	0.4628	1.4823	0.3462	0.047*
C2	0.6200 (2)	1.3707 (3)	0.27696 (18)	0.0397 (6)
H2	0.6282	1.4556	0.2264	0.048*
C3	0.7056 (2)	1.2095 (3)	0.29085 (15)	0.0284 (5)
H3	0.7750	1.1776	0.2505	0.034*
C4	0.67230 (19)	1.1077 (3)	0.37123 (14)	0.0235 (4)
C5	0.7319 (2)	0.9239 (3)	0.40399 (14)	0.0251 (5)
H5A	0.6570	0.8341	0.4000	0.030*
H5B	0.7985	0.8860	0.3583	0.030*
C6	0.80265 (18)	0.9232 (3)	0.50691 (14)	0.0210 (4)
C7	0.89494 (19)	0.8130 (3)	0.65241 (14)	0.0237 (4)
C8	0.81250 (19)	0.5733 (3)	0.52706 (15)	0.0248 (5)
H8A	0.7248	0.5633	0.4858	0.030*
H8B	0.8064	0.4951	0.5846	0.030*
C9	0.92978 (19)	0.5042 (3)	0.46888 (15)	0.0244 (5)
H9A	0.9380	0.5847	0.4125	0.029*
H9B	0.9062	0.3823	0.4434	0.029*
O1	0.93269 (14)	0.7093 (2)	0.72214 (10)	0.0320 (4)
S1	0.53875 (6)	1.20931 (8)	0.42809 (4)	0.03579 (19)
N1	0.84314 (16)	1.0686 (2)	0.55781 (12)	0.0254 (4)
N2	0.90101 (17)	0.9981 (2)	0.64778 (12)	0.0266 (4)
H2'	0.9371	1.0656	0.6957	0.032*
N3	0.83149 (16)	0.7636 (2)	0.56012 (12)	0.0200 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0331 (13)	0.0302 (13)	0.0520 (16)	0.0050 (10)	−0.0071 (11)	0.0078 (11)
C2	0.0412 (14)	0.0391 (14)	0.0369 (14)	−0.0028 (11)	−0.0063 (11)	0.0165 (11)
C3	0.0285 (11)	0.0312 (12)	0.0244 (11)	−0.0029 (9)	−0.0033 (8)	0.0032 (10)
C4	0.0203 (10)	0.0272 (11)	0.0221 (11)	−0.0024 (8)	−0.0030 (8)	0.0000 (9)
C5	0.0279 (10)	0.0252 (11)	0.0216 (11)	−0.0005 (9)	−0.0012 (8)	−0.0007 (9)
C6	0.0191 (10)	0.0209 (10)	0.0231 (10)	0.0014 (8)	0.0022 (8)	−0.0001 (8)
C7	0.0215 (10)	0.0282 (12)	0.0216 (11)	0.0043 (9)	0.0025 (8)	0.0001 (9)
C8	0.0263 (10)	0.0184 (10)	0.0296 (11)	−0.0022 (9)	0.0018 (8)	0.0004 (9)
C9	0.0306 (11)	0.0158 (10)	0.0267 (11)	0.0007 (8)	0.0017 (9)	−0.0024 (8)
O1	0.0368 (9)	0.0353 (9)	0.0233 (8)	0.0089 (7)	−0.0009 (6)	0.0072 (7)
S1	0.0333 (3)	0.0339 (3)	0.0407 (4)	0.0060 (2)	0.0061 (2)	0.0053 (3)
N1	0.0292 (9)	0.0219 (9)	0.0243 (9)	0.0014 (7)	−0.0023 (7)	−0.0008 (7)
N2	0.0330 (10)	0.0257 (10)	0.0198 (9)	0.0010 (8)	−0.0052 (7)	−0.0043 (7)
N3	0.0219 (8)	0.0176 (8)	0.0205 (9)	0.0018 (6)	0.0009 (7)	0.0002 (7)

Geometric parameters (Å, º) top

O1—C7	1.235 (2)	N1—N2	1.388 (2)
C8—N3	1.460 (2)	C7—N2	1.348 (3)
C8—C9	1.519 (3)	C6—C5	1.492 (3)
C8—H8A	0.9700	N2—H2'	0.8600
C8—H8B	0.9700	C3—C4	1.377 (3)
C9—C9ⁱ	1.525 (4)	C3—C2	1.434 (3)
C9—H9A	0.9700	C3—H3	0.9300
C9—H9B	0.9700	C4—C5	1.504 (3)
S1—C1	1.706 (2)	C5—H5A	0.9700
S1—C4	1.723 (2)	C5—H5B	0.9700
N3—C6	1.380 (2)	C1—C2	1.348 (3)
N3—C7	1.385 (2)	C1—H1	0.9300
N1—C6	1.301 (2)	C2—H2	0.9300

N3—C8—C9	113.22 (15)	N3—C6—C5	122.84 (17)
N3—C8—H8A	108.9	C7—N2—N1	113.17 (16)
C9—C8—H8A	108.9	C7—N2—H2'	123.4
N3—C8—H8B	108.9	N1—N2—H2'	123.4
C9—C8—H8B	108.9	C4—C3—C2	111.7 (2)
H8A—C8—H8B	107.7	C4—C3—H3	124.1
C8—C9—C9ⁱ	112.9 (2)	C2—C3—H3	124.1
C8—C9—H9A	109.0	C3—C4—C5	126.86 (19)
C9ⁱ—C9—H9A	109.0	C3—C4—S1	111.03 (16)
C8—C9—H9B	109.0	C5—C4—S1	121.92 (14)
C9ⁱ—C9—H9B	109.0	C6—C5—C4	114.00 (16)
H9A—C9—H9B	107.8	C6—C5—H5A	108.8
C1—S1—C4	92.17 (11)	C4—C5—H5A	108.8
C6—N3—C7	107.60 (16)	C6—C5—H5B	108.8
C6—N3—C8	128.57 (16)	C4—C5—H5B	108.8
C7—N3—C8	123.64 (16)	H5A—C5—H5B	107.6
C6—N1—N2	103.88 (16)	C2—C1—S1	112.09 (18)
O1—C7—N2	129.31 (19)	C2—C1—H1	124.0
O1—C7—N3	127.11 (19)	S1—C1—H1	124.0
N2—C7—N3	103.56 (16)	C1—C2—C3	113.0 (2)
N1—C6—N3	111.79 (17)	C1—C2—H2	123.5
N1—C6—C5	125.37 (17)	C3—C2—H2	123.5

N3—C8—C9—C9ⁱ	64.5 (3)	N3—C7—N2—N1	0.8 (2)
C9—C8—N3—C6	80.8 (2)	C6—N1—N2—C7	−0.6 (2)
C9—C8—N3—C7	−93.6 (2)	C2—C3—C4—C5	175.11 (18)
C6—N3—C7—O1	177.72 (18)	C2—C3—C4—S1	−0.1 (2)
C8—N3—C7—O1	−6.9 (3)	C1—S1—C4—C3	0.25 (16)
C6—N3—C7—N2	−0.60 (19)	C1—S1—C4—C5	−175.20 (16)
C8—N3—C7—N2	174.81 (16)	N1—C6—C5—C4	−16.6 (3)
N2—N1—C6—N3	0.2 (2)	N3—C6—C5—C4	162.63 (17)
N2—N1—C6—C5	179.48 (17)	C3—C4—C5—C6	120.9 (2)
C7—N3—C6—N1	0.3 (2)	S1—C4—C5—C6	−64.4 (2)
C8—N3—C6—N1	−174.84 (17)	C4—S1—C1—C2	−0.39 (19)
C7—N3—C6—C5	−179.06 (17)	S1—C1—C2—C3	0.4 (3)
C8—N3—C6—C5	5.8 (3)	C4—C3—C2—C1	−0.2 (3)
O1—C7—N2—N1	−177.51 (18)

Symmetry code: (i) −x+2, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2′···O1ⁱⁱ	0.86	1.91	2.737 (2)	161

Symmetry code: (ii) −x+2, y+1/2, −z+3/2.

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3,3′-Bis(2-thienylmeth­yl)-4,4′-(butane-1,4-di­yl)bis­(4,5-dihydro-1H-1,2,4-triazol-5-one)

Supporting information

Key indicators

checkCIF/PLATON results

3,3′-Bis(2-thienylmethyl)-4,4′-(butane-1,4-diyl)bis(4,5-dihydro-1H-1,2,4-triazol-5-one)