2-(4-tert-Butyl­phen­yl)-5-{3,4-dibutoxy-5-[5-(4-tert-butyl­phen­yl)-1,3,4-oxadiazol-2-yl]-2-thienyl}-1,3,4-oxadiazole

Guan, J.; Li, H.; Han, L.; Wang, H.

doi:10.1107/S1600536808033953

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page o2154

doi:10.1107/S1600536808033953

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2-(4-tert-Butylphenyl)-5-{3,4-dibutoxy-5-[5-(4-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]-2-thienyl}-1,3,4-oxadiazole

Jian-ning Guan,^a Hai-lin Li,^a Lu-na Han ^a and Hai-bo Wang ^a ^*

^aCollege of Science, Nanjing University of Technology, Xinmofan Road No. 5 Nanjing, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: wanghaibo@njut.edu.cn

(Received 13 October 2008; accepted 17 October 2008; online 22 October 2008)

In the title compound, C₃₆H₄₄N₄O₄S, the dihedral angles between the central thiophene ring and the pendent oxadiazole rings are 12.7 (2) and 13.7 (2)°, and the dihedral angles between the oxadiazole rings and their adjacent benzene rings are 6.1 (2) and 17.5 (2)°. An intramolecular C—H⋯O interaction may help to establish the conformation.

Related literature

For background, see: Laurent et al. (2005 ).

Experimental

Crystal data

C₃₆H₄₄N₄O₄S
M_r = 628.81
Monoclinic, P 2₁ /c
a = 19.421 (4) Å
b = 17.387 (4) Å
c = 10.424 (2) Å
β = 94.24 (3)°
V = 3510.3 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.14 mm⁻¹
T = 293 (2) K
0.20 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.974, T_max = 0.987
6675 measured reflections
6295 independent reflections
2847 reflections with I > 2σ(I)
R_int = 0.032
3 standard reflections every 200 reflections intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.085
wR(F²) = 0.164
S = 1.06
6295 reflections
391 parameters
138 restraints
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C36—H36B⋯O2	0.97	2.50	3.149 (6)	124

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); 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: SHELXS97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808033953/hb2818sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808033953/hb2818Isup2.hkl

checkCIF report

Comment top

Some thiophene derivatives possess biological properties (Laurent et al., 2005). As part of our studies in this area, we report here the synthesis and crystal structure of the title compound, (I).

An intramolecular C—H···O hydrogen bond (Table 1) may help to establish the molecular conformation of (I). The molecular structure of (I) is shown in Fig. 1 and relevant dihedral angles are given in the Abstract.

Related literature top

For background, see: Laurent et al. (2005).

Experimental top

3,4-Dibutoxythiophene-2,5-dicarbohydrazide (10 mmol) was dissolved in pyridine (30 ml) and 4-tert-butylbenzoyl chloride (22 mmol) was added dropwise to the mixture. The resulting mixture was heated to 342 K for 12 h. After cooling, the mixture was poured onto ice water and a white solid was obtained.

The crude compound was dissolved in phosphoryl trichloride (30 ml) and the mixture was refluxed for 12 h. After cooling, the mixture was poured onto crushed ice. The title compound was obtained and purified by recrystalization from trichloromethane. Yield is 85% and melting point is 421 K. Yellow blocks of (I) suitable were obtained by slow evaporation of an ethyl acetate solution.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); 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: SHELXS97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I) with displacement ellipsoids for the non-hydrogen atoms drawn at the 30% probability level.

2-(4-tert-Butylphenyl)-5-{3,4-dibutoxy-5-[5-(4-tert-butylphenyl)- 1,3,4-oxadiazol-2-yl]-2-thienyl}-1,3,4-oxadiazole top

Crystal data top

C₃₆H₄₄N₄O₄S	F(000) = 1344
M_r = 628.81	D_x = 1.190 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 421 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 19.421 (4) Å	Cell parameters from 25 reflections
b = 17.387 (4) Å	θ = 9–12°
c = 10.424 (2) Å	µ = 0.14 mm⁻¹
β = 94.24 (3)°	T = 293 K
V = 3510.3 (12) Å³	Block, yellow
Z = 4	0.20 × 0.10 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	2847 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.032
Graphite monochromator	θ_max = 25.2°, θ_min = 1.1°
ω/2θ scans	h = −23→23
Absorption correction: ψ scan (North et al., 1968)	k = 0→20
T_min = 0.974, T_max = 0.987	l = 0→12
6675 measured reflections	3 standard reflections every 200 reflections
6295 independent reflections	intensity decay: none

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)] = 0.085	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.164	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.03P)² + 3P] where P = (F_o² + 2F_c²)/3
6295 reflections	(Δ/σ)_max < 0.001
391 parameters	Δρ_max = 0.17 e Å⁻³
138 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₃₆H₄₄N₄O₄S	V = 3510.3 (12) Å³
M_r = 628.81	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 19.421 (4) Å	µ = 0.14 mm⁻¹
b = 17.387 (4) Å	T = 293 K
c = 10.424 (2) Å	0.20 × 0.10 × 0.10 mm
β = 94.24 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2847 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.032
T_min = 0.974, T_max = 0.987	3 standard reflections every 200 reflections
6675 measured reflections	intensity decay: none
6295 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.085	138 restraints
wR(F²) = 0.164	H-atom parameters constrained
S = 1.06	Δρ_max = 0.17 e Å⁻³
6295 reflections	Δρ_min = −0.21 e Å⁻³
391 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
S	0.21507 (6)	0.13771 (7)	0.42321 (11)	0.0737 (4)
O1	0.10436 (14)	0.25970 (16)	0.6562 (2)	0.0669 (8)
O2	0.36725 (13)	0.19395 (15)	0.2071 (2)	0.0642 (8)
O3	0.21365 (18)	0.3469 (2)	0.5488 (3)	0.0970 (11)
O4	0.32043 (16)	0.32198 (19)	0.3699 (3)	0.0894 (10)
N1	0.1172 (2)	0.1352 (2)	0.6394 (4)	0.0923 (12)
N2	0.0679 (2)	0.1487 (2)	0.7245 (4)	0.0867 (12)
N3	0.3300 (2)	0.0804 (2)	0.2671 (4)	0.0836 (12)
N4	0.3820 (2)	0.0680 (2)	0.1858 (4)	0.0888 (13)
C1	−0.15814 (18)	0.3412 (2)	1.1340 (4)	0.1110 (19)
H1B	−0.1926	0.3703	1.1743	0.167*
H1C	−0.1222	0.3265	1.1974	0.167*
H1D	−0.1788	0.2959	1.0951	0.167*
C2	−0.18704 (18)	0.4193 (2)	0.9408 (4)	0.122 (2)
H2B	−0.2195	0.4461	0.9898	0.183*
H2C	−0.2096	0.3766	0.8970	0.183*
H2D	−0.1696	0.4538	0.8789	0.183*
C3	−0.0929 (2)	0.4586 (3)	1.0956 (5)	0.1034 (18)
H3B	−0.1263	0.4876	1.1389	0.155*
H3C	−0.0733	0.4905	1.0326	0.155*
H3D	−0.0571	0.4412	1.1571	0.155*
C4	−0.1275 (2)	0.3906 (3)	1.0304 (5)	0.0951 (17)
C5	−0.0756 (2)	0.3445 (3)	0.9573 (4)	0.0738 (13)
C6	−0.0359 (2)	0.3824 (3)	0.8756 (4)	0.0907 (15)
H6A	−0.0387	0.4357	0.8684	0.109*
C7	0.0083 (2)	0.3422 (3)	0.8037 (4)	0.0863 (14)
H7A	0.0339	0.3694	0.7469	0.104*
C8	0.0163 (2)	0.2667 (3)	0.8112 (4)	0.0670 (12)
C9	−0.0241 (2)	0.2255 (3)	0.8991 (4)	0.0895 (15)
H9A	−0.0211	0.1724	0.9071	0.107*
C10	−0.0676 (3)	0.2678 (3)	0.9712 (4)	0.0862 (14)
H10A	−0.0922	0.2424	1.0315	0.103*
C11	0.0613 (2)	0.2196 (3)	0.7351 (4)	0.0669 (12)
C12	0.1359 (2)	0.1992 (3)	0.5977 (4)	0.0680 (12)
C13	0.6959 (3)	0.1763 (3)	−0.0922 (5)	0.1127 (19)
H13A	0.7334	0.1850	−0.1454	0.169*
H13B	0.6959	0.1233	−0.0659	0.169*
H13C	0.7013	0.2087	−0.0176	0.169*
C14	0.62126 (18)	0.1443 (2)	−0.2875 (3)	0.1019 (17)
H14A	0.6589	0.1547	−0.3397	0.153*
H14B	0.5783	0.1550	−0.3359	0.153*
H14C	0.6224	0.0912	−0.2623	0.153*
C15	0.63464 (18)	0.2763 (2)	−0.2131 (3)	0.1153 (19)
H15A	0.6726	0.2798	−0.2668	0.173*
H15B	0.6429	0.3095	−0.1401	0.173*
H15C	0.5928	0.2916	−0.2613	0.173*
C16	0.6278 (2)	0.1950 (3)	−0.1681 (4)	0.0737 (13)
C17	0.5690 (2)	0.1827 (3)	−0.0836 (4)	0.0673 (12)
C18	0.5604 (2)	0.1117 (3)	−0.0274 (4)	0.0725 (13)
H18A	0.5914	0.0725	−0.0422	0.087*
C19	0.5093 (2)	0.0977 (3)	0.0467 (4)	0.0779 (13)
H19A	0.5057	0.0493	0.0834	0.093*
C20	0.4595 (2)	0.1557 (3)	0.0719 (4)	0.0649 (11)
C21	0.4679 (2)	0.2243 (3)	0.0192 (4)	0.0732 (13)
H21A	0.4371	0.2635	0.0357	0.088*
C22	0.5210 (2)	0.2397 (3)	−0.0600 (4)	0.0735 (12)
H22A	0.5244	0.2880	−0.0972	0.088*
C23	0.4030 (2)	0.1344 (3)	0.1547 (4)	0.0662 (12)
C24	0.3240 (2)	0.1546 (3)	0.2765 (4)	0.0656 (12)
C25	0.2752 (2)	0.1947 (3)	0.3536 (4)	0.0642 (11)
C26	0.2736 (2)	0.2678 (3)	0.3940 (4)	0.0637 (11)
C27	0.2228 (2)	0.2800 (3)	0.4822 (4)	0.0711 (13)
C28	0.1870 (2)	0.2153 (3)	0.5084 (4)	0.0668 (12)
C29	0.1698 (4)	0.5589 (4)	0.4059 (7)	0.163 (3)
H29A	0.1491	0.6006	0.3566	0.245*
H29B	0.1763	0.5159	0.3502	0.245*
H29C	0.2137	0.5749	0.4454	0.245*
C30	0.1233 (4)	0.5356 (4)	0.5085 (7)	0.153 (3)
H30A	0.1163	0.5762	0.5700	0.184*
H30B	0.0793	0.5151	0.4740	0.184*
C31	0.1722 (3)	0.4753 (3)	0.5594 (6)	0.123 (2)
H31A	0.2154	0.5013	0.5839	0.148*
H31B	0.1547	0.4566	0.6383	0.148*
C32	0.1891 (3)	0.4099 (4)	0.4886 (6)	0.129 (2)
H32A	0.1479	0.3950	0.4364	0.155*
H32B	0.2229	0.4258	0.4298	0.155*
C33	0.4367 (3)	0.5060 (4)	0.1190 (6)	0.146 (2)
H33A	0.4471	0.5140	0.0314	0.218*
H33B	0.4774	0.4888	0.1686	0.218*
H33C	0.4211	0.5534	0.1541	0.218*
C34	0.3837 (3)	0.4491 (4)	0.1234 (6)	0.137 (2)
H34A	0.3964	0.4057	0.0715	0.165*
H34B	0.3415	0.4705	0.0826	0.165*
C35	0.3683 (3)	0.4197 (3)	0.2492 (5)	0.1124 (19)
H35A	0.3565	0.4634	0.3011	0.135*
H35B	0.4107	0.3981	0.2893	0.135*
C36	0.3132 (3)	0.3612 (3)	0.2580 (5)	0.1072 (18)
H36A	0.2685	0.3865	0.2510	0.129*
H36B	0.3146	0.3254	0.1868	0.129*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S	0.0887 (8)	0.0642 (7)	0.0711 (7)	−0.0006 (7)	0.0253 (6)	−0.0056 (7)
O1	0.0741 (18)	0.0740 (19)	0.0540 (16)	0.0001 (15)	0.0148 (14)	−0.0039 (15)
O2	0.0681 (17)	0.0533 (17)	0.0740 (19)	0.0009 (15)	0.0247 (15)	−0.0071 (15)
O3	0.130 (3)	0.079 (3)	0.083 (2)	0.008 (2)	0.021 (2)	−0.028 (2)
O4	0.097 (2)	0.082 (2)	0.092 (2)	−0.028 (2)	0.017 (2)	−0.004 (2)
N1	0.126 (3)	0.066 (3)	0.088 (3)	0.006 (2)	0.033 (2)	−0.008 (2)
N2	0.118 (3)	0.063 (2)	0.082 (3)	0.000 (2)	0.033 (2)	−0.012 (2)
N3	0.094 (3)	0.070 (3)	0.089 (3)	−0.006 (2)	0.024 (2)	−0.005 (2)
N4	0.120 (3)	0.056 (3)	0.098 (3)	0.001 (2)	0.056 (3)	0.001 (2)
C1	0.108 (4)	0.121 (5)	0.110 (4)	0.015 (4)	0.045 (3)	−0.007 (4)
C2	0.100 (4)	0.136 (5)	0.127 (5)	0.019 (4)	−0.010 (4)	−0.001 (4)
C3	0.084 (3)	0.098 (4)	0.133 (5)	0.003 (3)	0.038 (3)	−0.037 (4)
C4	0.062 (3)	0.105 (4)	0.124 (4)	0.023 (3)	0.046 (3)	−0.004 (4)
C5	0.082 (3)	0.071 (3)	0.070 (3)	−0.010 (3)	0.018 (2)	−0.005 (3)
C6	0.102 (4)	0.079 (3)	0.095 (3)	0.000 (3)	0.031 (3)	−0.005 (3)
C7	0.090 (3)	0.088 (3)	0.082 (3)	0.006 (3)	0.021 (3)	0.004 (3)
C8	0.072 (3)	0.070 (3)	0.062 (3)	0.001 (2)	0.020 (2)	−0.016 (2)
C9	0.112 (4)	0.081 (3)	0.082 (3)	0.014 (3)	0.045 (3)	0.003 (3)
C10	0.114 (4)	0.071 (3)	0.077 (3)	−0.012 (3)	0.032 (3)	0.001 (3)
C11	0.068 (3)	0.077 (3)	0.056 (3)	0.005 (2)	0.010 (2)	0.002 (2)
C12	0.077 (3)	0.074 (3)	0.054 (3)	0.011 (3)	0.011 (2)	0.001 (2)
C13	0.094 (4)	0.140 (5)	0.105 (4)	0.006 (4)	0.016 (3)	0.009 (4)
C14	0.120 (4)	0.108 (4)	0.083 (4)	0.004 (3)	0.041 (3)	−0.008 (3)
C15	0.109 (4)	0.117 (5)	0.121 (5)	−0.010 (4)	0.011 (4)	0.003 (4)
C16	0.083 (3)	0.083 (3)	0.056 (3)	−0.001 (3)	0.014 (2)	−0.002 (3)
C17	0.066 (3)	0.076 (3)	0.060 (3)	0.001 (2)	0.007 (2)	−0.008 (2)
C18	0.080 (3)	0.068 (3)	0.070 (3)	0.018 (2)	0.009 (2)	−0.001 (2)
C19	0.094 (3)	0.073 (3)	0.067 (3)	0.018 (3)	0.006 (3)	−0.001 (2)
C20	0.067 (3)	0.066 (3)	0.062 (3)	0.008 (2)	0.000 (2)	−0.010 (2)
C21	0.086 (3)	0.057 (3)	0.077 (3)	0.011 (2)	0.009 (2)	−0.015 (2)
C22	0.075 (3)	0.067 (3)	0.078 (3)	0.006 (2)	0.007 (2)	−0.005 (2)
C23	0.079 (3)	0.061 (3)	0.059 (3)	0.020 (3)	0.011 (2)	−0.003 (3)
C24	0.056 (3)	0.079 (3)	0.062 (3)	0.005 (2)	0.008 (2)	−0.008 (3)
C25	0.061 (3)	0.074 (3)	0.059 (3)	0.002 (2)	0.012 (2)	−0.011 (2)
C26	0.070 (3)	0.060 (3)	0.060 (3)	−0.003 (2)	0.001 (2)	−0.005 (2)
C27	0.080 (3)	0.061 (3)	0.073 (3)	0.005 (3)	0.014 (3)	−0.015 (3)
C28	0.071 (3)	0.084 (3)	0.047 (2)	0.004 (3)	0.020 (2)	−0.012 (2)
C29	0.181 (7)	0.152 (7)	0.153 (7)	0.007 (6)	−0.013 (6)	0.002 (5)
C30	0.171 (7)	0.133 (6)	0.159 (7)	0.013 (6)	0.029 (6)	−0.011 (5)
C31	0.160 (6)	0.084 (4)	0.126 (5)	0.014 (4)	0.016 (5)	0.006 (4)
C32	0.138 (6)	0.119 (6)	0.127 (6)	0.032 (5)	−0.015 (4)	0.000 (5)
C33	0.147 (6)	0.143 (6)	0.149 (6)	−0.011 (5)	0.023 (5)	0.027 (5)
C34	0.128 (6)	0.140 (6)	0.143 (6)	−0.023 (5)	−0.002 (5)	0.009 (5)
C35	0.095 (4)	0.119 (5)	0.123 (5)	−0.027 (4)	0.008 (4)	0.029 (4)
C36	0.106 (4)	0.105 (4)	0.111 (5)	0.003 (4)	0.006 (4)	0.024 (4)

Geometric parameters (Å, º) top

S—C28	1.726 (4)	C14—H14B	0.9600
S—C25	1.732 (4)	C14—H14C	0.9600
O1—C12	1.382 (5)	C15—C16	1.499 (5)
O1—C11	1.402 (4)	C15—H15A	0.9600
O2—C24	1.336 (4)	C15—H15B	0.9600
O2—C23	1.380 (4)	C15—H15C	0.9600
O3—C32	1.334 (6)	C16—C17	1.507 (5)
O3—C27	1.374 (5)	C17—C18	1.383 (5)
O4—C26	1.345 (5)	C17—C22	1.394 (5)
O4—C36	1.349 (5)	C18—C19	1.324 (5)
N1—C12	1.259 (5)	C18—H18A	0.9300
N1—N2	1.372 (5)	C19—C20	1.434 (5)
N2—C11	1.245 (5)	C19—H19A	0.9300
N3—C24	1.300 (5)	C20—C21	1.329 (5)
N3—N4	1.383 (4)	C20—C23	1.493 (5)
N4—C23	1.275 (5)	C21—C22	1.394 (5)
C1—C4	1.533 (6)	C21—H21A	0.9300
C1—H1B	0.9600	C22—H22A	0.9300
C1—H1C	0.9600	C24—C25	1.464 (5)
C1—H1D	0.9600	C25—C26	1.340 (5)
C2—C4	1.517 (6)	C26—C27	1.414 (5)
C2—H2B	0.9600	C27—C28	1.359 (5)
C2—H2C	0.9599	C29—C30	1.506 (8)
C2—H2D	0.9600	C29—H29A	0.9600
C3—C4	1.497 (6)	C29—H29B	0.9600
C3—H3B	0.9600	C29—H29C	0.9600
C3—H3C	0.9600	C30—C31	1.487 (8)
C3—H3D	0.9600	C30—H30A	0.9700
C4—C5	1.533 (6)	C30—H30B	0.9700
C5—C10	1.350 (6)	C31—C32	1.407 (6)
C5—C6	1.361 (5)	C31—H31A	0.9700
C6—C7	1.371 (6)	C31—H31B	0.9700
C6—H6A	0.9300	C32—H32A	0.9700
C7—C8	1.324 (5)	C32—H32B	0.9700
C7—H7A	0.9300	C33—C34	1.432 (7)
C8—C9	1.440 (5)	C33—H33A	0.9600
C8—C11	1.471 (5)	C33—H33B	0.9600
C9—C10	1.382 (5)	C33—H33C	0.9600
C9—H9A	0.9300	C34—C35	1.458 (7)
C10—H10A	0.9300	C34—H34A	0.9700
C12—C28	1.438 (5)	C34—H34B	0.9700
C13—C16	1.526 (6)	C35—C36	1.485 (6)
C13—H13A	0.9600	C35—H35A	0.9700
C13—H13B	0.9600	C35—H35B	0.9700
C13—H13C	0.9600	C36—H36A	0.9700
C14—C16	1.523 (5)	C36—H36B	0.9700
C14—H14A	0.9600

C28—S—C25	90.9 (2)	C22—C17—C16	123.2 (4)
C12—O1—C11	100.6 (3)	C19—C18—C17	122.0 (4)
C24—O2—C23	100.6 (3)	C19—C18—H18A	119.0
C32—O3—C27	120.9 (4)	C17—C18—H18A	119.0
C26—O4—C36	119.1 (4)	C18—C19—C20	121.5 (4)
C12—N1—N2	107.8 (4)	C18—C19—H19A	119.2
C11—N2—N1	108.0 (4)	C20—C19—H19A	119.2
C24—N3—N4	105.9 (3)	C21—C20—C19	116.8 (4)
C23—N4—N3	106.0 (3)	C21—C20—C23	125.3 (4)
C4—C1—H1B	109.5	C19—C20—C23	117.8 (4)
C4—C1—H1C	109.5	C20—C21—C22	122.3 (4)
H1B—C1—H1C	109.5	C20—C21—H21A	118.9
C4—C1—H1D	109.5	C22—C21—H21A	118.9
H1B—C1—H1D	109.5	C17—C22—C21	120.2 (4)
H1C—C1—H1D	109.5	C17—C22—H22A	119.9
C4—C2—H2B	109.5	C21—C22—H22A	119.9
C4—C2—H2C	109.8	N4—C23—O2	113.6 (4)
H2B—C2—H2C	109.5	N4—C23—C20	129.3 (4)
C4—C2—H2D	109.2	O2—C23—C20	117.1 (4)
H2B—C2—H2D	109.5	N3—C24—O2	113.8 (3)
H2C—C2—H2D	109.5	N3—C24—C25	125.4 (4)
C4—C3—H3B	109.5	O2—C24—C25	120.8 (4)
C4—C3—H3C	109.5	C26—C25—C24	131.0 (4)
H3B—C3—H3C	109.5	C26—C25—S	112.2 (3)
C4—C3—H3D	109.5	C24—C25—S	116.2 (3)
H3B—C3—H3D	109.5	C25—C26—O4	124.9 (4)
H3C—C3—H3D	109.5	C25—C26—C27	112.3 (4)
C3—C4—C2	108.3 (4)	O4—C26—C27	122.1 (4)
C3—C4—C5	110.4 (4)	C28—C27—O3	120.8 (4)
C2—C4—C5	111.4 (4)	C28—C27—C26	113.5 (4)
C3—C4—C1	107.9 (4)	O3—C27—C26	125.3 (4)
C2—C4—C1	107.5 (3)	C27—C28—C12	132.8 (4)
C5—C4—C1	111.2 (4)	C27—C28—S	111.0 (3)
C10—C5—C6	118.6 (4)	C12—C28—S	116.1 (3)
C10—C5—C4	122.5 (4)	C30—C29—H29A	109.5
C6—C5—C4	118.8 (4)	C30—C29—H29B	109.5
C5—C6—C7	120.1 (5)	H29A—C29—H29B	109.5
C5—C6—H6A	120.0	C30—C29—H29C	109.5
C7—C6—H6A	120.0	H29A—C29—H29C	109.5
C8—C7—C6	123.3 (5)	H29B—C29—H29C	109.5
C8—C7—H7A	118.3	C31—C30—C29	92.4 (6)
C6—C7—H7A	118.3	C31—C30—H30A	113.2
C7—C8—C9	117.6 (4)	C29—C30—H30A	113.2
C7—C8—C11	126.3 (4)	C31—C30—H30B	113.2
C9—C8—C11	116.1 (4)	C29—C30—H30B	113.2
C10—C9—C8	117.7 (4)	H30A—C30—H30B	110.6
C10—C9—H9A	121.1	C32—C31—C30	123.4 (6)
C8—C9—H9A	121.1	C32—C31—H31A	106.5
C5—C10—C9	122.5 (4)	C30—C31—H31A	106.5
C5—C10—H10A	118.7	C32—C31—H31B	106.5
C9—C10—H10A	118.7	C30—C31—H31B	106.5
N2—C11—O1	111.8 (4)	H31A—C31—H31B	106.5
N2—C11—C8	131.9 (4)	O3—C32—C31	120.4 (6)
O1—C11—C8	116.3 (4)	O3—C32—H32A	107.2
N1—C12—O1	111.8 (4)	C31—C32—H32A	107.2
N1—C12—C28	128.9 (4)	O3—C32—H32B	107.2
O1—C12—C28	119.1 (4)	C31—C32—H32B	107.2
C16—C13—H13A	109.5	H32A—C32—H32B	106.9
C16—C13—H13B	109.5	C34—C33—H33A	109.5
H13A—C13—H13B	109.5	C34—C33—H33B	109.5
C16—C13—H13C	109.5	H33A—C33—H33B	109.5
H13A—C13—H13C	109.5	C34—C33—H33C	109.5
H13B—C13—H13C	109.5	H33A—C33—H33C	109.5
C16—C14—H14A	109.5	H33B—C33—H33C	109.5
C16—C14—H14B	109.5	C33—C34—C35	117.8 (6)
H14A—C14—H14B	109.5	C33—C34—H34A	107.9
C16—C14—H14C	109.5	C35—C34—H34A	107.9
H14A—C14—H14C	109.5	C33—C34—H34B	107.9
H14B—C14—H14C	109.5	C35—C34—H34B	107.9
C16—C15—H15A	109.5	H34A—C34—H34B	107.2
C16—C15—H15B	109.5	C34—C35—C36	119.5 (5)
H15A—C15—H15B	109.5	C34—C35—H35A	107.5
C16—C15—H15C	109.5	C36—C35—H35A	107.5
H15A—C15—H15C	109.5	C34—C35—H35B	107.5
H15B—C15—H15C	109.5	C36—C35—H35B	107.5
C15—C16—C17	113.9 (4)	H35A—C35—H35B	107.0
C15—C16—C14	107.1 (3)	O4—C36—C35	111.7 (5)
C17—C16—C14	112.1 (4)	O4—C36—H36A	109.3
C15—C16—C13	105.6 (4)	C35—C36—H36A	109.3
C17—C16—C13	109.4 (4)	O4—C36—H36B	109.3
C14—C16—C13	108.5 (4)	C35—C36—H36B	109.3
C18—C17—C22	117.1 (4)	H36A—C36—H36B	107.9
C18—C17—C16	119.6 (4)

C28—S—C25—C24	172.5 (3)	C9—C8—C11—N2	6.1 (7)
C28—S—C25—C26	0.4 (3)	C8—C9—C10—C5	3.3 (7)
C25—S—C28—C12	−175.5 (3)	N1—C12—C28—S	13.7 (6)
C25—S—C28—C27	0.1 (3)	O1—C12—C28—S	−171.4 (3)
C12—O1—C11—N2	0.8 (4)	N1—C12—C28—C27	−160.6 (5)
C12—O1—C11—C8	−177.9 (3)	O1—C12—C28—C27	14.3 (7)
C11—O1—C12—N1	−2.8 (4)	C13—C16—C17—C18	−57.0 (6)
C11—O1—C12—C28	−178.6 (4)	C13—C16—C17—C22	124.3 (5)
C24—O2—C23—N4	1.9 (5)	C14—C16—C17—C18	63.2 (5)
C24—O2—C23—C20	−177.8 (4)	C14—C16—C17—C22	−115.5 (5)
C23—O2—C24—N3	−1.5 (4)	C15—C16—C17—C18	−174.9 (4)
C23—O2—C24—C25	178.9 (4)	C15—C16—C17—C22	6.5 (6)
C32—O3—C27—C26	70.3 (6)	C22—C17—C18—C19	−0.6 (6)
C32—O3—C27—C28	−117.5 (5)	C16—C17—C22—C21	179.8 (4)
C27—O3—C32—C31	172.5 (5)	C16—C17—C18—C19	−179.3 (4)
C36—O4—C26—C25	84.4 (6)	C18—C17—C22—C21	1.2 (6)
C36—O4—C26—C27	−105.3 (5)	C17—C18—C19—C20	0.5 (7)
C26—O4—C36—C35	178.6 (4)	C18—C19—C20—C21	−1.0 (6)
N2—N1—C12—O1	3.8 (5)	C18—C19—C20—C23	178.9 (4)
N2—N1—C12—C28	179.0 (4)	C23—C20—C21—C22	−178.3 (4)
C12—N1—N2—C11	−3.2 (5)	C19—C20—C23—O2	162.7 (4)
N1—N2—C11—O1	1.4 (5)	C19—C20—C23—N4	−16.9 (7)
N1—N2—C11—C8	179.7 (4)	C21—C20—C23—O2	−17.4 (6)
C24—N3—N4—C23	0.6 (5)	C19—C20—C21—C22	1.7 (6)
N4—N3—C24—O2	0.7 (5)	C21—C20—C23—N4	163.0 (5)
N4—N3—C24—C25	−179.7 (4)	C20—C21—C22—C17	−1.8 (7)
N3—N4—C23—C20	178.1 (4)	O2—C24—C25—S	172.4 (3)
N3—N4—C23—O2	−1.6 (5)	N3—C24—C25—S	−7.1 (6)
C1—C4—C5—C6	−170.1 (4)	N3—C24—C25—C26	163.2 (5)
C3—C4—C5—C10	129.2 (5)	O2—C24—C25—C26	−17.2 (7)
C3—C4—C5—C6	−50.5 (6)	S—C25—C26—O4	170.4 (3)
C2—C4—C5—C10	−110.3 (5)	C24—C25—C26—C27	−171.4 (4)
C1—C4—C5—C10	9.5 (6)	S—C25—C26—C27	−0.7 (5)
C2—C4—C5—C6	70.0 (5)	C24—C25—C26—O4	−0.2 (8)
C10—C5—C6—C7	3.9 (7)	O4—C26—C27—C28	−170.7 (4)
C4—C5—C10—C9	175.7 (4)	C25—C26—C27—O3	173.5 (4)
C6—C5—C10—C9	−4.7 (7)	C25—C26—C27—C28	0.8 (5)
C4—C5—C6—C7	−176.5 (4)	O4—C26—C27—O3	2.0 (7)
C5—C6—C7—C8	−1.9 (7)	O3—C27—C28—S	−173.5 (3)
C6—C7—C8—C9	0.5 (6)	O3—C27—C28—C12	1.0 (7)
C6—C7—C8—C11	178.3 (4)	C26—C27—C28—S	−0.5 (5)
C9—C8—C11—O1	−175.6 (3)	C26—C27—C28—C12	174.1 (4)
C7—C8—C11—O1	6.6 (6)	C29—C30—C31—C32	−64.9 (7)
C7—C8—C11—N2	−171.8 (5)	C30—C31—C32—O3	−157.7 (6)
C7—C8—C9—C10	−1.1 (6)	C33—C34—C35—C36	179.3 (5)
C11—C8—C9—C10	−179.2 (4)	C34—C35—C36—O4	159.5 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C36—H36B···O2	0.97	2.50	3.149 (6)	124

Experimental details

Crystal data
Chemical formula	C₃₆H₄₄N₄O₄S
M_r	628.81
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	19.421 (4), 17.387 (4), 10.424 (2)
β (°)	94.24 (3)
V (Å³)	3510.3 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.14
Crystal size (mm)	0.20 × 0.10 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.974, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	6675, 6295, 2847
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.085, 0.164, 1.06
No. of reflections	6295
No. of parameters	391
No. of restraints	138
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.21

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), 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
C36—H36B···O2	0.97	2.50	3.149 (6)	124

References

Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
Laurent, B., Evelyne, M. & Adrien, N. (2005). Eur. J. Med. Chem. 40, 757–763. Web of Science PubMed Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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Volume 64| Part 11| November 2008| Page o2154

doi:10.1107/S1600536808033953

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

2-(4-tert-Butyl­phen­yl)-5-{3,4-di­but­oxy-5-[5-(4-tert-butyl­phen­yl)-1,3,4-oxa­diazol-2-yl]-2-thienyl}-1,3,4-oxa­diazole

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

2-(4-tert-Butylphenyl)-5-{3,4-dibutoxy-5-[5-(4-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]-2-thienyl}-1,3,4-oxadiazole