Dimethyl 3,3′-diphenyl-2,2′-[(S)-thio­phene-2,5-diylbis(carbonyl­aza­nedi­yl)]dipropano­ate tetra­hydro­furan monosolvate

Xia, G.M.; Liu, J.; Li, Z.; Ji, M.W.; Sun, G.X.

doi:10.1107/S1600536810034410

organic compounds

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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page o2489

doi:10.1107/S1600536810034410

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Dimethyl 3,3′-diphenyl-2,2′-[(S)-thiophene-2,5-diylbis(carbonylazanediyl)]dipropanoate tetrahydrofuran monosolvate

GuangMing Xia,^a ^* Jing Liu,^a Zhen Li,^b MuWei Ji ^a and GuoXin Sun ^a

^aShandong Provincial Key Laboratory of Fluorine Chemistry and Chemical Materials, School of Chemistry and Chemical Engineering, University of Jinan, Ji'nan 250022, People's Republic of China, and ^bSchool of Chemistry and Chemical Engineering, University of Jinan, Ji'nan 250022, People's Republic of China
^*Correspondence e-mail: chm_xiagm@ujn.edu.cn

(Received 6 August 2010; accepted 26 August 2010; online 4 September 2010)

The title compound, C₂₆H₂₆N₂O₆S·C₄H₈O, a solvated bis-amide derivative, is also a chiral amino acid ester with L-phenylalanine methyl ester groups as amine substituents. The thiophene-2,5-dicarboxamide core approximates C₂ point symmetry. The tetrahydrofuran solvent molecule is linked to the main molecule through an intermolecular N—H⋯O hydrogen bond. The central ring makes dihedral angles of 90.0 (2) and 76.5 (2)° with the pendant rings.

Related literature

For applications of thiophene derivatives, see: Zhao et al. (2009 ). For the synthesis of the title compound, see: Moriuchi et al. (2006 ). For the structure of the unsolvated molecule, see: Xia et al. (2010 ).

Experimental

Crystal data

C₂₆H₂₆N₂O₆S·C₄H₈O
M_r = 566.65
Orthorhombic, P 2₁ 2₁ 2₁
a = 8.3041 (3) Å
b = 12.1810 (4) Å
c = 29.6787 (11) Å
V = 3002.06 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.16 mm⁻¹
T = 293 K
0.40 × 0.21 × 0.08 mm

Data collection

Oxford Xcalibur (Eos) CCD detector diffractometer
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.941, T_max = 0.988
7782 measured reflections
5081 independent reflections
3167 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.094
S = 0.91
5081 reflections
363 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.21 e Å⁻³
Absolute structure: Flack (1983 ), 1964 Friedel pairs
Flack parameter: −0.05 (9)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O7	0.86	2.02	2.859 (3)	164

Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO CCD; data reduction: CrysAlis PRO RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810034410/bh2306sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810034410/bh2306Isup2.hkl

checkCIF report

Comment top

The thiophene derivatives have been viewed as significant compounds for applications in many fields, such as photo-materials, electronic luminescence materials (Zhao et al., 2009). The title compound derives from thiophene-2,5-dicarboxylic acid and a natural amino acid. This makes this kind of structures very promising for biological activities and as precursors in the synthesis of various compounds.

In the structure of the title compound, the thiophene-2,5-dicarboxamide core approximates C₂ point symmetry. The molecules are connected by intermolecular N—H···O hydrogen-bonding interactions with tetrahydrofuran molecules. Chiral atoms C3 and C19 in the main molecule retain the absolute S configuration of the parent L-phenylalanine. The procedure used for the synthesis of the title compound is thus carried-out without inversion for chiral centers. The structure of the unsolvated molecule with identical absolute configuration has been determined (Xia et al., 2010).

Related literature top

For applications of thiophene derivatives, see: Zhao et al. (2009). For the synthesis of the title compound, see: Moriuchi et al. (2006). For the structure of the unsolvated molecule, see: Xia et al. (2010).

Experimental top

A mixture of 2,5-thiophenedicarboxylic acid (0.3 mmol), thionyl chloride (3 mmol) and 3–5 drops of N,N-dimethylformamide in a flask was heated to 343 K for 10 h. The resulting solution was evaporated under vacuum, affording 2,5-thiophenedicarbonyldichloride as a pale yellow product.

The title compound was synthesized by a slight modification of a procedure described by Moriuchi et al. (2006). To a stirred mixture of L-phenylalanine methyl ester hydrochloride (129.4 mg, 0.6 mmol in 15 ml of dry dichloromethane) and triethylamine (0.21 ml, 1.5 mmol) was added dropwise 2,5-thiophenedicarbonyldichloride (62.7 mg, 0.3 mmol) in dichloromethane (3 ml) at 253 K and then 20 h at 293 K. The resulting mixture was diluted with dichloromethane, washed with saturated NaHCO₃ solution and brine, and then dried over anhydrous MgSO₄. The solvent was removed in vacuo. The title compound was isolated as a white solid by crystallization from 2-propanol (yield: 129.6 mg, 78%). Then the product was recrystallized from THF, to yield colourless blocks of the title solvate.

Computing details top

Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO CCD (Oxford Diffraction, 2009); data reduction: CrysAlis PRO RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The title structure with thermal ellipsoids at 30% probability level.

Dimethyl 3,3'-diphenyl-2,2'-[(S)-thiophene-2,5- diylbis(carbonylazanediyl)]dipropanoate tetrahydrofuran monosolvate top

Crystal data top

C₂₆H₂₆N₂O₆S·C₄H₈O	F(000) = 1200
M_r = 566.65	D_x = 1.254 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3062 reflections
a = 8.3041 (3) Å	θ = 3.0–28.8°
b = 12.1810 (4) Å	µ = 0.16 mm⁻¹
c = 29.6787 (11) Å	T = 293 K
V = 3002.06 (17) Å³	Block, colourless
Z = 4	0.40 × 0.21 × 0.08 mm

Data collection top

Oxford Xcalibur (Eos) CCD detector diffractometer	5081 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3167 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
Detector resolution: 16.0355 pixels mm^-1	θ_max = 25.3°, θ_min = 3.0°
ω scans	h = −9→9
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009)	k = −14→12
T_min = 0.941, T_max = 0.988	l = −15→35
7782 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)] = 0.047	H-atom parameters constrained
wR(F²) = 0.094	w = 1/[σ²(F_o²) + (0.0458P)²] where P = (F_o² + 2F_c²)/3
S = 0.91	(Δ/σ)_max < 0.001
5081 reflections	Δρ_max = 0.19 e Å⁻³
363 parameters	Δρ_min = −0.21 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1964 Friedel pairs
0 constraints	Absolute structure parameter: −0.05 (9)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₂₆H₂₆N₂O₆S·C₄H₈O	V = 3002.06 (17) Å³
M_r = 566.65	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 8.3041 (3) Å	µ = 0.16 mm⁻¹
b = 12.1810 (4) Å	T = 293 K
c = 29.6787 (11) Å	0.40 × 0.21 × 0.08 mm

Data collection top

Oxford Xcalibur (Eos) CCD detector diffractometer	5081 independent reflections
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009)	3167 reflections with I > 2σ(I)
T_min = 0.941, T_max = 0.988	R_int = 0.022
7782 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	H-atom parameters constrained
wR(F²) = 0.094	Δρ_max = 0.19 e Å⁻³
S = 0.91	Δρ_min = −0.21 e Å⁻³
5081 reflections	Absolute structure: Flack (1983), 1964 Friedel pairs
363 parameters	Absolute structure parameter: −0.05 (9)
0 restraints

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

	x	y	z	U_iso*/U_eq
C1	0.7362 (4)	−0.1856 (4)	−0.38825 (15)	0.0993 (14)
H1A	0.7425	−0.2168	−0.3586	0.149*
H1B	0.7790	−0.1124	−0.3878	0.149*
H1C	0.7976	−0.2297	−0.4088	0.149*
C2	0.4695 (4)	−0.1250 (3)	−0.37793 (13)	0.0615 (9)
C3	0.2978 (3)	−0.1273 (2)	−0.39603 (10)	0.0476 (8)
H3	0.2785	−0.2003	−0.4089	0.057*
C4	0.2776 (4)	−0.0426 (2)	−0.43389 (11)	0.0555 (8)
H4A	0.2911	0.0305	−0.4215	0.067*
H4B	0.3615	−0.0538	−0.4562	0.067*
C5	0.1160 (4)	−0.0496 (2)	−0.45669 (10)	0.0466 (8)
C6	0.0864 (4)	−0.1295 (3)	−0.48868 (12)	0.0638 (9)
H6	0.1673	−0.1793	−0.4960	0.077*
C7	−0.0602 (5)	−0.1369 (3)	−0.50983 (13)	0.0782 (11)
H7	−0.0772	−0.1897	−0.5319	0.094*
C8	−0.1798 (5)	−0.0671 (4)	−0.49844 (15)	0.0794 (12)
H8	−0.2804	−0.0741	−0.5119	0.095*
C9	−0.1543 (5)	0.0131 (3)	−0.46754 (16)	0.0804 (12)
H9	−0.2361	0.0624	−0.4606	0.097*
C10	−0.0064 (4)	0.0216 (2)	−0.44637 (11)	0.0628 (9)
H10	0.0102	0.0761	−0.4249	0.075*
C11	0.1316 (3)	−0.1966 (3)	−0.33570 (10)	0.0476 (7)
C12	0.0384 (3)	−0.1773 (2)	−0.29456 (10)	0.0428 (7)
C13	−0.0220 (4)	−0.0850 (2)	−0.27630 (10)	0.0588 (9)
H13	−0.0123	−0.0160	−0.2894	0.071*
C14	−0.1017 (4)	−0.1042 (2)	−0.23495 (12)	0.0609 (9)
H14	−0.1489	−0.0490	−0.2178	0.073*
C15	−0.1023 (3)	−0.2104 (2)	−0.22293 (9)	0.0425 (7)
C16	−0.1644 (3)	−0.2650 (2)	−0.18143 (10)	0.0410 (7)
C17	−0.7408 (4)	−0.3073 (4)	−0.15049 (14)	0.1109 (16)
H17A	−0.8026	−0.2648	−0.1294	0.166*
H17B	−0.7452	−0.3834	−0.1422	0.166*
H17C	−0.7846	−0.2983	−0.1802	0.166*
C18	−0.4957 (4)	−0.2807 (2)	−0.11222 (12)	0.0541 (8)
C19	−0.3256 (3)	−0.2374 (2)	−0.11366 (10)	0.0449 (7)
H19	−0.2553	−0.2970	−0.1034	0.054*
C20	−0.3044 (3)	−0.1424 (2)	−0.08026 (11)	0.0543 (9)
H20B	−0.3664	−0.0799	−0.0906	0.065*
H20A	−0.3466	−0.1643	−0.0511	0.065*
C21	−0.1327 (4)	−0.1090 (3)	−0.07497 (11)	0.0532 (9)
C22	−0.0324 (4)	−0.1616 (3)	−0.04495 (12)	0.0687 (10)
H22	−0.0732	−0.2182	−0.0273	0.082*
C23	0.1266 (6)	−0.1322 (4)	−0.04062 (16)	0.0960 (14)
H23	0.1916	−0.1688	−0.0200	0.115*
C24	0.1900 (6)	−0.0506 (5)	−0.0661 (2)	0.1118 (18)
H24	0.2977	−0.0309	−0.0634	0.134*
C25	0.0910 (7)	0.0024 (4)	−0.0962 (2)	0.1108 (16)
H25	0.1327	0.0587	−0.1139	0.133*
C26	−0.0682 (5)	−0.0260 (3)	−0.10075 (14)	0.0785 (11)
H26	−0.1327	0.0111	−0.1214	0.094*
C27	−0.5480 (9)	−0.0480 (5)	−0.2287 (2)	0.210 (4)
H27A	−0.4867	−0.0942	−0.2490	0.252*
H27B	−0.6468	−0.0857	−0.2207	0.252*
C28	−0.5824 (9)	0.0546 (6)	−0.2491 (2)	0.184 (3)
H28B	−0.6961	0.0597	−0.2563	0.221*
H28A	−0.5211	0.0629	−0.2767	0.221*
C29	−0.5388 (8)	0.1382 (5)	−0.2175 (2)	0.170 (3)
H29B	−0.6284	0.1875	−0.2121	0.204*
H29A	−0.4480	0.1806	−0.2285	0.204*
C30	−0.4949 (7)	0.0780 (4)	−0.17561 (19)	0.1219 (16)
H30A	−0.4048	0.1133	−0.1607	0.146*
H30B	−0.5854	0.0758	−0.1550	0.146*
N1	0.1852 (3)	−0.11168 (19)	−0.35934 (8)	0.0479 (6)
H1	0.1527	−0.0466	−0.3528	0.057*
N2	−0.2705 (2)	−0.20642 (19)	−0.15812 (8)	0.0430 (6)
H2	−0.3083	−0.1474	−0.1700	0.052*
O1	0.5682 (3)	−0.1824 (2)	−0.40280 (8)	0.0745 (7)
O2	0.5104 (3)	−0.0779 (3)	−0.34523 (11)	0.1289 (13)
O3	0.1599 (3)	−0.29143 (18)	−0.34747 (8)	0.0910 (8)
O4	−0.1172 (2)	−0.35693 (15)	−0.17022 (7)	0.0555 (6)
O5	−0.5526 (3)	−0.3183 (3)	−0.07888 (10)	0.1001 (9)
O6	−0.5731 (3)	−0.2699 (2)	−0.15000 (9)	0.0818 (8)
O7	−0.4551 (4)	−0.0230 (2)	−0.18881 (12)	0.1181 (11)
S1	−0.00131 (10)	−0.28933 (5)	−0.26159 (3)	0.0543 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.054 (2)	0.142 (4)	0.102 (3)	0.014 (2)	0.001 (2)	0.028 (3)
C2	0.060 (2)	0.079 (2)	0.045 (2)	−0.0056 (19)	0.004 (2)	−0.0055 (19)
C3	0.0561 (19)	0.0494 (17)	0.037 (2)	−0.0002 (15)	0.0048 (17)	−0.0052 (16)
C4	0.064 (2)	0.0541 (19)	0.048 (2)	−0.0067 (16)	0.0060 (19)	−0.0004 (17)
C5	0.0574 (18)	0.0435 (17)	0.039 (2)	−0.0019 (16)	0.0095 (17)	0.0004 (16)
C6	0.073 (2)	0.062 (2)	0.056 (2)	0.0068 (18)	0.002 (2)	−0.015 (2)
C7	0.090 (3)	0.081 (3)	0.064 (3)	−0.006 (2)	−0.011 (2)	−0.014 (2)
C8	0.077 (3)	0.083 (3)	0.079 (3)	−0.003 (2)	−0.019 (3)	0.016 (3)
C9	0.075 (3)	0.073 (3)	0.093 (4)	0.020 (2)	0.006 (3)	0.020 (3)
C10	0.080 (2)	0.0543 (18)	0.054 (2)	0.001 (2)	0.004 (2)	−0.0020 (16)
C11	0.0565 (17)	0.0441 (18)	0.042 (2)	0.0000 (16)	0.0048 (16)	−0.0058 (16)
C12	0.0481 (16)	0.0448 (16)	0.0357 (18)	−0.0063 (13)	0.0065 (15)	−0.0025 (14)
C13	0.083 (2)	0.0396 (16)	0.053 (2)	−0.0001 (17)	0.022 (2)	0.0063 (15)
C14	0.078 (2)	0.0443 (18)	0.061 (2)	0.0057 (15)	0.032 (2)	−0.0004 (17)
C15	0.0430 (14)	0.0451 (17)	0.0396 (19)	−0.0047 (13)	0.0040 (14)	−0.0019 (15)
C16	0.0402 (16)	0.0413 (17)	0.042 (2)	−0.0075 (13)	−0.0025 (15)	−0.0023 (15)
C17	0.058 (2)	0.169 (4)	0.106 (4)	−0.041 (3)	−0.019 (2)	0.003 (3)
C18	0.0449 (17)	0.0638 (18)	0.053 (2)	0.0000 (18)	0.006 (2)	0.0113 (18)
C19	0.0463 (17)	0.0491 (17)	0.0394 (19)	0.0077 (14)	0.0069 (16)	0.0049 (15)
C20	0.059 (2)	0.064 (2)	0.041 (2)	0.0049 (16)	0.0100 (17)	−0.0013 (17)
C21	0.063 (2)	0.052 (2)	0.044 (2)	−0.0059 (17)	0.0036 (19)	−0.0103 (17)
C22	0.070 (3)	0.075 (2)	0.062 (3)	0.0000 (19)	0.000 (2)	0.004 (2)
C23	0.080 (3)	0.123 (4)	0.085 (4)	−0.001 (3)	−0.019 (3)	−0.014 (3)
C24	0.070 (3)	0.142 (5)	0.123 (5)	−0.022 (3)	−0.009 (3)	−0.044 (4)
C25	0.111 (4)	0.107 (4)	0.115 (5)	−0.058 (3)	0.026 (4)	−0.003 (3)
C26	0.090 (3)	0.070 (2)	0.076 (3)	−0.021 (2)	0.004 (2)	0.009 (2)
C27	0.296 (9)	0.128 (4)	0.205 (8)	0.092 (5)	−0.165 (8)	−0.053 (5)
C28	0.273 (8)	0.179 (6)	0.100 (5)	0.115 (6)	−0.059 (5)	−0.021 (5)
C29	0.221 (7)	0.108 (4)	0.183 (7)	0.041 (4)	−0.082 (6)	0.015 (5)
C30	0.136 (4)	0.105 (3)	0.125 (4)	0.033 (3)	−0.008 (4)	−0.011 (3)
N1	0.0621 (15)	0.0417 (14)	0.0399 (17)	0.0044 (12)	0.0133 (14)	−0.0017 (12)
N2	0.0471 (13)	0.0418 (12)	0.0401 (15)	0.0052 (12)	0.0075 (12)	0.0059 (13)
O1	0.0563 (14)	0.0945 (17)	0.0728 (18)	0.0055 (13)	0.0091 (13)	−0.0053 (15)
O2	0.0844 (19)	0.212 (3)	0.090 (2)	0.004 (2)	−0.0221 (19)	−0.072 (2)
O3	0.141 (2)	0.0481 (14)	0.0839 (19)	−0.0028 (15)	0.0556 (17)	−0.0047 (14)
O4	0.0709 (13)	0.0386 (11)	0.0568 (16)	0.0086 (10)	0.0112 (12)	0.0071 (11)
O5	0.0672 (16)	0.151 (2)	0.082 (2)	−0.0221 (15)	0.0101 (14)	0.047 (2)
O6	0.0554 (13)	0.128 (2)	0.0623 (17)	−0.0274 (13)	−0.0090 (13)	0.0150 (16)
O7	0.161 (3)	0.0830 (19)	0.110 (3)	0.054 (2)	−0.056 (2)	−0.0078 (18)
S1	0.0711 (5)	0.0404 (4)	0.0516 (5)	0.0027 (4)	0.0181 (5)	0.0008 (4)

Geometric parameters (Å, º) top

C1—O1	1.461 (4)	C17—H17A	0.9600
C1—H1A	0.9600	C17—H17B	0.9600
C1—H1B	0.9600	C17—H17C	0.9600
C1—H1C	0.9600	C18—O5	1.188 (3)
C2—O2	1.178 (4)	C18—O6	1.299 (4)
C2—O1	1.306 (4)	C18—C19	1.509 (4)
C2—C3	1.524 (4)	C19—N2	1.446 (3)
C3—N1	1.448 (3)	C19—C20	1.533 (4)
C3—C4	1.535 (4)	C19—H19	0.9800
C3—H3	0.9800	C20—C21	1.491 (4)
C4—C5	1.506 (4)	C20—H20B	0.9700
C4—H4A	0.9700	C20—H20A	0.9700
C4—H4B	0.9700	C21—C26	1.377 (4)
C5—C10	1.371 (4)	C21—C22	1.378 (4)
C5—C6	1.382 (4)	C22—C23	1.374 (5)
C6—C7	1.373 (5)	C22—H22	0.9300
C6—H6	0.9300	C23—C24	1.357 (6)
C7—C8	1.350 (5)	C23—H23	0.9300
C7—H7	0.9300	C24—C25	1.374 (6)
C8—C9	1.357 (5)	C24—H24	0.9300
C8—H8	0.9300	C25—C26	1.373 (5)
C9—C10	1.383 (5)	C25—H25	0.9300
C9—H9	0.9300	C26—H26	0.9300
C10—H10	0.9300	C27—C28	1.417 (7)
C11—O3	1.229 (3)	C27—O7	1.445 (6)
C11—N1	1.327 (3)	C27—H27A	0.9700
C11—C12	1.465 (4)	C27—H27B	0.9700
C12—C13	1.345 (4)	C28—C29	1.430 (7)
C12—S1	1.711 (3)	C28—H28B	0.9700
C13—C14	1.414 (4)	C28—H28A	0.9700
C13—H13	0.9300	C29—C30	1.489 (6)
C14—C15	1.342 (4)	C29—H29B	0.9700
C14—H14	0.9300	C29—H29A	0.9700
C15—C16	1.491 (4)	C30—O7	1.333 (4)
C15—S1	1.716 (3)	C30—H30A	0.9700
C16—O4	1.232 (3)	C30—H30B	0.9700
C16—N2	1.328 (3)	N1—H1	0.8600
C17—O6	1.465 (4)	N2—H2	0.8600

O1—C1—H1A	109.5	O6—C18—C19	113.8 (3)
O1—C1—H1B	109.5	N2—C19—C18	114.4 (3)
H1A—C1—H1B	109.5	N2—C19—C20	110.9 (2)
O1—C1—H1C	109.5	C18—C19—C20	110.7 (2)
H1A—C1—H1C	109.5	N2—C19—H19	106.8
H1B—C1—H1C	109.5	C18—C19—H19	106.8
O2—C2—O1	123.1 (3)	C20—C19—H19	106.8
O2—C2—C3	124.7 (3)	C21—C20—C19	112.6 (2)
O1—C2—C3	112.2 (3)	C21—C20—H20B	109.1
N1—C3—C2	109.7 (3)	C19—C20—H20B	109.1
N1—C3—C4	113.1 (2)	C21—C20—H20A	109.1
C2—C3—C4	110.3 (2)	C19—C20—H20A	109.1
N1—C3—H3	107.9	H20B—C20—H20A	107.8
C2—C3—H3	107.9	C26—C21—C22	117.8 (3)
C4—C3—H3	107.9	C26—C21—C20	120.9 (3)
C5—C4—C3	112.8 (2)	C22—C21—C20	121.3 (3)
C5—C4—H4A	109.0	C23—C22—C21	121.3 (4)
C3—C4—H4A	109.0	C23—C22—H22	119.3
C5—C4—H4B	109.0	C21—C22—H22	119.3
C3—C4—H4B	109.0	C24—C23—C22	120.8 (4)
H4A—C4—H4B	107.8	C24—C23—H23	119.6
C10—C5—C6	117.9 (3)	C22—C23—H23	119.6
C10—C5—C4	121.7 (3)	C23—C24—C25	118.3 (4)
C6—C5—C4	120.5 (3)	C23—C24—H24	120.8
C7—C6—C5	121.2 (3)	C25—C24—H24	120.8
C7—C6—H6	119.4	C26—C25—C24	121.5 (5)
C5—C6—H6	119.4	C26—C25—H25	119.3
C8—C7—C6	119.8 (4)	C24—C25—H25	119.3
C8—C7—H7	120.1	C25—C26—C21	120.3 (4)
C6—C7—H7	120.1	C25—C26—H26	119.8
C7—C8—C9	120.5 (4)	C21—C26—H26	119.8
C7—C8—H8	119.7	C28—C27—O7	105.8 (5)
C9—C8—H8	119.7	C28—C27—H27A	110.6
C8—C9—C10	119.9 (4)	O7—C27—H27A	110.6
C8—C9—H9	120.0	C28—C27—H27B	110.6
C10—C9—H9	120.0	O7—C27—H27B	110.6
C5—C10—C9	120.7 (3)	H27A—C27—H27B	108.7
C5—C10—H10	119.7	C27—C28—C29	107.3 (5)
C9—C10—H10	119.7	C27—C28—H28B	110.3
O3—C11—N1	121.2 (3)	C29—C28—H28B	110.3
O3—C11—C12	119.3 (3)	C27—C28—H28A	110.3
N1—C11—C12	119.5 (3)	C29—C28—H28A	110.3
C13—C12—C11	131.8 (3)	H28B—C28—H28A	108.5
C13—C12—S1	111.4 (2)	C28—C29—C30	105.0 (5)
C11—C12—S1	116.8 (2)	C28—C29—H29B	110.8
C12—C13—C14	112.7 (3)	C30—C29—H29B	110.8
C12—C13—H13	123.7	C28—C29—H29A	110.8
C14—C13—H13	123.7	C30—C29—H29A	110.8
C15—C14—C13	113.1 (3)	H29B—C29—H29A	108.8
C15—C14—H14	123.4	O7—C30—C29	105.7 (4)
C13—C14—H14	123.4	O7—C30—H30A	110.6
C14—C15—C16	130.6 (3)	C29—C30—H30A	110.6
C14—C15—S1	111.1 (2)	O7—C30—H30B	110.6
C16—C15—S1	118.1 (2)	C29—C30—H30B	110.6
O4—C16—N2	123.9 (3)	H30A—C30—H30B	108.7
O4—C16—C15	121.2 (3)	C11—N1—C3	120.8 (2)
N2—C16—C15	114.8 (2)	C11—N1—H1	119.6
O6—C17—H17A	109.5	C3—N1—H1	119.6
O6—C17—H17B	109.5	C16—N2—C19	123.0 (2)
H17A—C17—H17B	109.5	C16—N2—H2	118.5
O6—C17—H17C	109.5	C19—N2—H2	118.5
H17A—C17—H17C	109.5	C2—O1—C1	116.5 (3)
H17B—C17—H17C	109.5	C18—O6—C17	116.6 (3)
O5—C18—O6	124.1 (3)	C30—O7—C27	107.6 (4)
O5—C18—C19	122.1 (3)	C12—S1—C15	91.70 (14)

O2—C2—C3—N1	−27.1 (5)	N2—C19—C20—C21	−61.3 (3)
O1—C2—C3—N1	152.6 (3)	C18—C19—C20—C21	170.6 (3)
O2—C2—C3—C4	98.1 (4)	C19—C20—C21—C26	93.0 (4)
O1—C2—C3—C4	−82.3 (3)	C19—C20—C21—C22	−85.4 (4)
N1—C3—C4—C5	−63.2 (3)	C26—C21—C22—C23	0.3 (5)
C2—C3—C4—C5	173.6 (3)	C20—C21—C22—C23	178.8 (3)
C3—C4—C5—C10	100.2 (3)	C21—C22—C23—C24	−0.4 (6)
C3—C4—C5—C6	−79.2 (4)	C22—C23—C24—C25	0.4 (7)
C10—C5—C6—C7	0.7 (5)	C23—C24—C25—C26	−0.2 (8)
C4—C5—C6—C7	−179.9 (3)	C24—C25—C26—C21	0.0 (7)
C5—C6—C7—C8	−2.0 (6)	C22—C21—C26—C25	−0.1 (5)
C6—C7—C8—C9	2.7 (6)	C20—C21—C26—C25	−178.6 (4)
C7—C8—C9—C10	−2.1 (6)	O7—C27—C28—C29	−11.0 (9)
C6—C5—C10—C9	−0.1 (5)	C27—C28—C29—C30	−6.4 (9)
C4—C5—C10—C9	−179.6 (3)	C28—C29—C30—O7	23.0 (7)
C8—C9—C10—C5	0.9 (5)	O3—C11—N1—C3	−8.9 (4)
O3—C11—C12—C13	−173.0 (3)	C12—C11—N1—C3	170.4 (2)
N1—C11—C12—C13	7.7 (5)	C2—C3—N1—C11	−87.8 (3)
O3—C11—C12—S1	8.6 (4)	C4—C3—N1—C11	148.6 (3)
N1—C11—C12—S1	−170.8 (2)	O4—C16—N2—C19	9.1 (4)
C11—C12—C13—C14	−178.4 (3)	C15—C16—N2—C19	−170.2 (2)
S1—C12—C13—C14	0.1 (3)	C18—C19—N2—C16	−107.0 (3)
C12—C13—C14—C15	−0.8 (4)	C20—C19—N2—C16	127.0 (3)
C13—C14—C15—C16	176.3 (3)	O2—C2—O1—C1	−0.3 (5)
C13—C14—C15—S1	1.2 (3)	C3—C2—O1—C1	−179.9 (3)
C14—C15—C16—O4	−159.8 (3)	O5—C18—O6—C17	−0.1 (5)
S1—C15—C16—O4	15.0 (3)	C19—C18—O6—C17	−178.2 (3)
C14—C15—C16—N2	19.5 (4)	C29—C30—O7—C27	−30.3 (6)
S1—C15—C16—N2	−165.68 (19)	C28—C27—O7—C30	26.6 (7)
O5—C18—C19—N2	173.3 (3)	C13—C12—S1—C15	0.5 (2)
O6—C18—C19—N2	−8.6 (4)	C11—C12—S1—C15	179.2 (2)
O5—C18—C19—C20	−60.6 (4)	C14—C15—S1—C12	−1.0 (2)
O6—C18—C19—C20	117.5 (3)	C16—C15—S1—C12	−176.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O7	0.86	2.02	2.859 (3)	164

Experimental details

Crystal data
Chemical formula	C₂₆H₂₆N₂O₆S·C₄H₈O
M_r	566.65
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	8.3041 (3), 12.1810 (4), 29.6787 (11)
V (Å³)	3002.06 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.16
Crystal size (mm)	0.40 × 0.21 × 0.08

Data collection
Diffractometer	Oxford Xcalibur (Eos) CCD detector diffractometer
Absorption correction	Multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009)
T_min, T_max	0.941, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	7782, 5081, 3167
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.094, 0.91
No. of reflections	5081
No. of parameters	363
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.21
Absolute structure	Flack (1983), 1964 Friedel pairs
Absolute structure parameter	−0.05 (9)

Computer programs: CrysAlis PRO CCD (Oxford Diffraction, 2009), CrysAlis PRO RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O7	0.86	2.02	2.859 (3)	163.5

Acknowledgements

This work was supported by the Shandong Key Scientific and Technological Project (2008 GG30002014) and the Project of the Key Laboratory of Photochemical Conversion and Optoelectronic Materials, TIPC, Chinese Academy of Sciences.

References

Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CrossRef CAS IUCr Journals Google Scholar
Moriuchi, T., Shen, X. & Hirao, T. (2006). Tetrahedron, 62, 12237–2246. Web of Science CSD CrossRef CAS Google Scholar
Oxford Diffraction (2009). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Xia, G.-M., Liu, J., Li, Z., Ji, M.-W. & Sun, G.-X. (2010). Acta Cryst. E66, o2385. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhao, L., Liang, J., Yue, G., Deng, X. & He, Y. (2009). Acta Cryst. E65, m722. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 66| Part 10| October 2010| Page o2489

doi:10.1107/S1600536810034410

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

Di­methyl 3,3′-di­phenyl-2,2′-[(S)-thio­phene-2,5-diylbis(carbonyl­aza­nedi­yl)]di­propano­ate tetra­hydro­furan monosolvate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Dimethyl 3,3′-diphenyl-2,2′-[(S)-thiophene-2,5-diylbis(carbonylazanediyl)]dipropanoate tetrahydrofuran monosolvate