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

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

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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808033953/hb2818sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536808033953/hb2818Isup2.hkl Contains datablock I

CCDC reference: 709690

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.007 Å
R factor = 0.085
wR factor = 0.164
Data-to-parameter ratio = 16.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         45 Perc.
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.57 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C3     --  C4      ..       6.83 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C4     --  C5      ..       6.16 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C15    --  C16     ..       5.92 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C30    --  C31     ..       5.42 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C34    --  C35     ..       5.32 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C32
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C5
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C16
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C31
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          7
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C31    -   C32    ...       1.41 Ang.
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C33    -   C34    ...       1.43 Ang.
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT234_ALERT_4_C Large Hirshfeld Difference O2     --  C24     ..       0.12  Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference N2     --  C11     ..       0.12  Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference N3     --  N4      ..       0.12  Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference N4     --  C23     ..       0.14  Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference C2     --  C4      ..       0.14  Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference C5     --  C6      ..       0.13  Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference C7     --  C8      ..       0.12  Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference C8     --  C11     ..       0.12  Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference C9     --  C10     ..       0.15  Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference C12    --  C28     ..       0.12  Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference C13    --  C16     ..       0.13  Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference C14    --  C16     ..       0.15  Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference C18    --  C19     ..       0.10  Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference C29    --  C30     ..       0.19  Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference C31    --  C32     ..       0.13  Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference C33    --  C34     ..       0.14  Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference C35    --  C36     ..       0.17  Ang.

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......        138
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  32 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  12 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
  17 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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).