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

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

doi:10.1107/S1600536810033210

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 9| September 2010| Page o2385

https://doi.org/10.1107/S1600536810033210

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

Guang-Ming Xia,^a ^* Jing Liu,^a Zhen Li,^a Mu-Wei Ji ^a and Guo-Xin 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
^*Correspondence e-mail: chm_xiagm@ujn.edu.cn

(Received 24 July 2010; accepted 18 August 2010; online 25 August 2010)

The asymmetric unit of the title compound, C₂₆H₂₆N₂O₆S, contains two independent molecules; each has twofold symmetry with the S atom and the mid-point of the C—C bond of the thiophene ring located on a twofold rotation axis. In the two molecules, the terminal benzene rings are oriented at dihedral angles of 65.8 (3) and 63.5 (3)° with respect to the central thiophene rings. The methoxycarbonyl group of one molecule is disordered over two positions with site-occupancy factors of 0.277 (12) and 0.723 (12). Intermolecular N—H⋯O hydrogen bonding is present in the crystal structure.

Related literature

For applications of thiophene derivatives, see: Xia et al. (2010 ).

Experimental

Crystal data

C₂₆H₂₆N₂O₆S
M_r = 494.56
Orthorhombic, P 2₁ 2₁ 2
a = 9.0769 (3) Å
b = 29.6371 (7) Å
c = 9.3767 (2) Å
V = 2522.45 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.17 mm⁻¹
T = 120 K
0.36 × 0.24 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini 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 = 0.867, T_max = 1.000
6802 measured reflections
4233 independent reflections
3315 reflections with I > 2σ(I)
R_int = 0.051

Refinement

R[F² > 2σ(F²)] = 0.068
wR(F²) = 0.187
S = 1.10
4233 reflections
288 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.90 e Å⁻³
Δρ_min = −0.70 e Å⁻³
Absolute structure: Flack (1983 ), 1669 Friedel pairs
Flack parameter: 0.00 (18)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O6	0.86	2.01	2.853 (5)	164
N2—H2⋯O3ⁱ	0.86	2.10	2.803 (5)	139
Symmetry code: (i) x, y, z-1.

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: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810033210/xu5003sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810033210/xu5003Isup2.hkl

checkCIF report

Comment top

The thiophene derivates have been viewed as significant compounds for application in many fields (Xia et al., 2010). The title compound derives from natural amino acids. This makes this kind of compounds promising for biological activities.

In the structure of the title compound, the carboxamide groups are approximately coplanar with thiophene ring, and the dihedral angle between thiophene ring and carboxamide is 3.2 (6)°. Title molecules are connected by intermolecular N—H···O hydrogen-bonding interactions forming a supramolecular frameworks. C3 and C16 are chiral atoms in the structure. And the chiral C atom which derived from L-phenylalanine kept its known S configuration for that the synthesis reaction did not befallen on the chiral C atom.

Related literature top

For applications of thiophene derivatives, see: Xia et al. (2010).

Experimental top

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

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), 2,5-thiophenedicarbonyldichloride (62.7 mg, 0.3 mmol) in dichloromethane (3 ml) was added dropwise 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 condensed 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.

Structure description top

For applications of thiophene derivatives, see: Xia et al. (2010).

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: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure with thermal ellipsoids at 30% probability levels.
	Fig. 2. A packing diagram of the title compound along c axis.

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

Crystal data top

C₂₆H₂₆N₂O₆S	F(000) = 1040
M_r = 494.56	D_x = 1.302 Mg m⁻³
Orthorhombic, P2₁2₁2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2 2ab	Cell parameters from 4047 reflections
a = 9.0769 (3) Å	θ = 3.4–25.3°
b = 29.6371 (7) Å	µ = 0.17 mm⁻¹
c = 9.3767 (2) Å	T = 120 K
V = 2522.45 (12) Å³	Block, colourless
Z = 4	0.36 × 0.24 × 0.10 mm

Data collection top

Oxford Diffraction Xcalibur Eos Gemini diffractometer	4233 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3315 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.051
Detector resolution: 16.0355 pixels mm^-1	θ_max = 25.0°, θ_min = 3.4°
ω scans	h = −6→10
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009)	k = −28→35
T_min = 0.867, T_max = 1.000	l = −7→11
6802 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)] = 0.068	H-atom parameters constrained
wR(F²) = 0.187	w = 1/[σ²(F_o²) + (0.1124P)² + 0.8367P] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max < 0.001
4233 reflections	Δρ_max = 0.90 e Å⁻³
288 parameters	Δρ_min = −0.70 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1669 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (18)

Crystal data top

C₂₆H₂₆N₂O₆S	V = 2522.45 (12) Å³
M_r = 494.56	Z = 4
Orthorhombic, P2₁2₁2	Mo Kα radiation
a = 9.0769 (3) Å	µ = 0.17 mm⁻¹
b = 29.6371 (7) Å	T = 120 K
c = 9.3767 (2) Å	0.36 × 0.24 × 0.10 mm

Data collection top

Oxford Diffraction Xcalibur Eos Gemini diffractometer	4233 independent reflections
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009)	3315 reflections with I > 2σ(I)
T_min = 0.867, T_max = 1.000	R_int = 0.051
6802 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.068	H-atom parameters constrained
wR(F²) = 0.187	Δρ_max = 0.90 e Å⁻³
S = 1.10	Δρ_min = −0.70 e Å⁻³
4233 reflections	Absolute structure: Flack (1983), 1669 Friedel pairs
288 parameters	Absolute structure parameter: 0.00 (18)
1 restraint

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	Occ. (<1)
C1	0.3969 (8)	0.6948 (2)	0.3748 (8)	0.0676 (18)
H1A	0.3112	0.6771	0.3529	0.101*
H1B	0.4259	0.7117	0.2920	0.101*
H1C	0.3745	0.7153	0.4512	0.101*
C2	0.6263 (6)	0.68418 (15)	0.4908 (5)	0.0361 (11)
C3	0.7416 (5)	0.65073 (14)	0.5404 (5)	0.0336 (11)
H3	0.7545	0.6551	0.6432	0.040*
C4	0.8884 (6)	0.66076 (14)	0.4700 (5)	0.0338 (11)
H4B	0.9036	0.6932	0.4685	0.041*
H4A	0.8855	0.6503	0.3720	0.041*
C5	1.0183 (6)	0.63839 (14)	0.5462 (4)	0.0325 (10)
C6	1.0574 (6)	0.59423 (18)	0.5155 (7)	0.0529 (15)
H6	1.0076	0.5782	0.4451	0.063*
C7	1.1729 (8)	0.5739 (2)	0.5915 (8)	0.069 (2)
H7	1.2017	0.5446	0.5691	0.083*
C8	1.2438 (6)	0.59686 (19)	0.6990 (7)	0.0549 (15)
H8	1.3177	0.5828	0.7514	0.066*
C9	1.2052 (7)	0.64021 (18)	0.7282 (6)	0.0521 (14)
H9	1.2551	0.6562	0.7985	0.063*
C10	1.0909 (6)	0.66065 (16)	0.6527 (5)	0.0433 (13)
H10	1.0635	0.6900	0.6753	0.052*
C11	0.6350 (5)	0.57915 (14)	0.6197 (4)	0.0281 (10)
C12	0.5668 (5)	0.53566 (13)	0.5707 (4)	0.0281 (10)
C13	0.5371 (6)	0.52036 (15)	0.4374 (4)	0.0352 (12)
H13	0.5639	0.5357	0.3548	0.042*
C14A	0.207 (2)	0.6027 (7)	0.130 (2)	0.047 (4)	0.275 (12)
H14B	0.1740	0.5900	0.0411	0.070*	0.275 (12)
H14C	0.1380	0.6250	0.1616	0.070*	0.275 (12)
H14A	0.2147	0.5792	0.1999	0.070*	0.275 (12)
C14B	0.3361 (17)	0.5483 (4)	0.091 (2)	0.123 (6)	0.725 (12)
H14E	0.2938	0.5485	−0.0026	0.184*	0.725 (12)
H14F	0.2793	0.5674	0.1529	0.184*	0.725 (12)
H14D	0.3359	0.5181	0.1280	0.184*	0.725 (12)
C15	0.4767 (9)	0.6062 (2)	0.0647 (6)	0.0674 (7)
C16	0.6251 (9)	0.6243 (2)	0.0738 (7)	0.0674 (7)
H16	0.6438	0.6299	0.1752	0.081*
C17	0.6498 (9)	0.6692 (2)	−0.0017 (7)	0.0674 (7)
H17A	0.6582	0.6638	−0.1034	0.081*
H17B	0.5646	0.6883	0.0137	0.081*
C18	0.7826 (9)	0.6931 (2)	0.0477 (6)	0.0674 (7)
C19	0.7774 (9)	0.7261 (2)	0.1503 (6)	0.0674 (7)
H19	0.6853	0.7354	0.1822	0.081*
C20	0.9003 (9)	0.7463 (2)	0.2091 (7)	0.0674 (7)
H20	0.8902	0.7686	0.2783	0.081*
C21	1.0373 (9)	0.7331 (2)	0.1643 (6)	0.0674 (7)
H21	1.1207	0.7472	0.2008	0.081*
C22	1.0519 (9)	0.6990 (2)	0.0649 (6)	0.0674 (7)
H22	1.1448	0.6886	0.0389	0.081*
C23	0.9280 (9)	0.6808 (2)	0.0052 (7)	0.0674 (7)
H23	0.9391	0.6594	−0.0666	0.081*
C24	0.8109 (6)	0.56624 (14)	0.1212 (4)	0.0287 (10)
C25	0.9113 (5)	0.53145 (14)	0.0658 (4)	0.0284 (10)
C26	0.9493 (6)	0.51816 (16)	−0.0702 (4)	0.0395 (13)
H26	0.9124	0.5315	−0.1526	0.047*
N1	0.6976 (4)	0.60424 (11)	0.5186 (4)	0.0276 (8)
H1	0.7127	0.5923	0.4364	0.033*
N2	0.7346 (5)	0.59066 (12)	0.0283 (4)	0.0378 (10)
H2	0.7497	0.5867	−0.0614	0.045*
O1	0.5160 (5)	0.66529 (11)	0.4175 (4)	0.0507 (10)
O2	0.6327 (4)	0.72365 (11)	0.5165 (5)	0.0555 (11)
O3	0.6321 (4)	0.59001 (10)	0.7462 (3)	0.0403 (9)
O4A	0.342 (2)	0.6223 (6)	0.111 (2)	0.047 (4)	0.275 (12)
O4B	0.4741 (16)	0.5635 (4)	0.0848 (17)	0.078 (3)	0.725 (12)
O5A	0.443 (6)	0.5668 (8)	0.057 (5)	0.078 (3)	0.275 (12)
O5B	0.3754 (8)	0.6338 (3)	0.0463 (11)	0.070 (2)	0.725 (12)
O6	0.8024 (4)	0.57171 (10)	0.2509 (3)	0.0349 (8)
S1	0.5000	0.5000	0.70005 (14)	0.0268 (4)
S2	1.0000	0.5000	0.19249 (14)	0.0265 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.063 (4)	0.068 (4)	0.072 (4)	0.008 (3)	−0.025 (4)	−0.005 (3)
C2	0.042 (3)	0.030 (2)	0.037 (2)	0.007 (2)	0.012 (2)	0.0014 (19)
C3	0.041 (3)	0.033 (2)	0.027 (2)	−0.002 (2)	−0.002 (2)	−0.0013 (18)
C4	0.050 (3)	0.029 (2)	0.022 (2)	−0.007 (2)	0.000 (2)	−0.0004 (17)
C5	0.033 (3)	0.034 (2)	0.030 (2)	−0.001 (2)	0.004 (2)	−0.0016 (18)
C6	0.048 (3)	0.051 (3)	0.059 (3)	0.006 (3)	−0.013 (3)	−0.030 (3)
C7	0.073 (4)	0.055 (3)	0.081 (4)	0.031 (3)	−0.026 (4)	−0.038 (3)
C8	0.046 (3)	0.059 (3)	0.060 (3)	0.018 (3)	−0.018 (3)	−0.013 (3)
C9	0.054 (4)	0.052 (3)	0.051 (3)	0.004 (3)	−0.009 (3)	−0.020 (3)
C10	0.053 (3)	0.033 (2)	0.044 (3)	0.003 (2)	−0.009 (3)	−0.008 (2)
C11	0.035 (3)	0.031 (2)	0.018 (2)	0.004 (2)	−0.0055 (19)	0.0008 (16)
C12	0.041 (3)	0.027 (2)	0.0163 (19)	0.002 (2)	0.0030 (19)	0.0048 (16)
C13	0.056 (4)	0.035 (2)	0.015 (2)	−0.012 (2)	−0.005 (2)	0.0033 (17)
C14A	0.034 (7)	0.053 (8)	0.053 (8)	−0.013 (5)	0.010 (6)	0.002 (6)
C14B	0.110 (12)	0.068 (7)	0.191 (16)	−0.018 (7)	−0.066 (11)	0.014 (8)
C15	0.0996 (18)	0.0573 (12)	0.0455 (11)	0.0261 (13)	0.0108 (12)	−0.0013 (9)
C16	0.0996 (18)	0.0573 (12)	0.0455 (11)	0.0261 (13)	0.0108 (12)	−0.0013 (9)
C17	0.0996 (18)	0.0573 (12)	0.0455 (11)	0.0261 (13)	0.0108 (12)	−0.0013 (9)
C18	0.0996 (18)	0.0573 (12)	0.0455 (11)	0.0261 (13)	0.0108 (12)	−0.0013 (9)
C19	0.0996 (18)	0.0573 (12)	0.0455 (11)	0.0261 (13)	0.0108 (12)	−0.0013 (9)
C20	0.0996 (18)	0.0573 (12)	0.0455 (11)	0.0261 (13)	0.0108 (12)	−0.0013 (9)
C21	0.0996 (18)	0.0573 (12)	0.0455 (11)	0.0261 (13)	0.0108 (12)	−0.0013 (9)
C22	0.0996 (18)	0.0573 (12)	0.0455 (11)	0.0261 (13)	0.0108 (12)	−0.0013 (9)
C23	0.0996 (18)	0.0573 (12)	0.0455 (11)	0.0261 (13)	0.0108 (12)	−0.0013 (9)
C24	0.040 (3)	0.026 (2)	0.020 (2)	−0.002 (2)	0.000 (2)	−0.0021 (17)
C25	0.039 (3)	0.024 (2)	0.022 (2)	−0.0018 (19)	0.000 (2)	0.0001 (16)
C26	0.069 (4)	0.036 (2)	0.013 (2)	0.008 (2)	−0.002 (2)	0.0005 (16)
N1	0.044 (2)	0.0221 (16)	0.0167 (16)	−0.0009 (17)	−0.0006 (17)	−0.0027 (14)
N2	0.065 (3)	0.0338 (19)	0.0141 (16)	0.018 (2)	−0.0050 (19)	−0.0061 (14)
O1	0.054 (2)	0.0389 (18)	0.059 (2)	0.0089 (18)	−0.026 (2)	−0.0115 (16)
O2	0.057 (3)	0.0316 (19)	0.078 (3)	0.0055 (18)	−0.012 (2)	−0.0154 (17)
O3	0.066 (2)	0.0395 (17)	0.0156 (15)	−0.0111 (17)	−0.0077 (16)	−0.0038 (13)
O4A	0.034 (7)	0.053 (8)	0.053 (8)	−0.013 (5)	0.010 (6)	0.002 (6)
O4B	0.047 (8)	0.115 (4)	0.072 (8)	0.011 (4)	−0.005 (4)	0.048 (4)
O5A	0.047 (8)	0.115 (4)	0.072 (8)	0.011 (4)	−0.005 (4)	0.048 (4)
O5B	0.041 (4)	0.070 (5)	0.100 (6)	0.020 (4)	−0.026 (4)	−0.014 (4)
O6	0.049 (2)	0.0383 (16)	0.0170 (15)	0.0106 (16)	−0.0037 (14)	−0.0017 (12)
S1	0.0425 (9)	0.0263 (7)	0.0118 (6)	0.0010 (7)	0.000	0.000
S2	0.0384 (8)	0.0268 (7)	0.0144 (6)	0.0011 (7)	0.000	0.000

Geometric parameters (Å, º) top

C1—O1	1.447 (7)	C14B—H14E	0.9600
C1—H1A	0.9600	C14B—H14F	0.9600
C1—H1B	0.9600	C14B—H14D	0.9600
C1—H1C	0.9600	C15—O5A	1.21 (2)
C2—O2	1.196 (5)	C15—O5B	1.243 (9)
C2—O1	1.337 (6)	C15—O4B	1.280 (12)
C2—C3	1.515 (7)	C15—O4A	1.38 (2)
C3—N1	1.449 (6)	C15—C16	1.453 (11)
C3—C4	1.516 (7)	C16—N2	1.471 (7)
C3—H3	0.9800	C16—C17	1.523 (9)
C4—C5	1.530 (7)	C16—H16	0.9800
C4—H4B	0.9700	C17—C18	1.472 (10)
C4—H4A	0.9700	C17—H17A	0.9700
C5—C10	1.366 (7)	C17—H17B	0.9700
C5—C6	1.386 (7)	C18—C19	1.373 (8)
C6—C7	1.404 (9)	C18—C23	1.426 (10)
C6—H6	0.9300	C19—C20	1.381 (10)
C7—C8	1.376 (8)	C19—H19	0.9300
C7—H7	0.9300	C20—C21	1.369 (10)
C8—C9	1.360 (8)	C20—H20	0.9300
C8—H8	0.9300	C21—C22	1.381 (9)
C9—C10	1.395 (8)	C21—H21	0.9300
C9—H9	0.9300	C22—C23	1.367 (10)
C10—H10	0.9300	C22—H22	0.9300
C11—O3	1.229 (5)	C23—H23	0.9300
C11—N1	1.332 (6)	C24—O6	1.229 (5)
C11—C12	1.502 (6)	C24—N2	1.328 (6)
C12—C13	1.357 (6)	C24—C25	1.471 (6)
C12—S1	1.719 (4)	C25—C26	1.378 (6)
C13—C13ⁱ	1.383 (9)	C25—S2	1.711 (4)
C13—H13	0.9300	C26—C26ⁱⁱ	1.417 (10)
C14A—O4A	1.37 (3)	C26—H26	0.9300
C14A—H14B	0.9600	N1—H1	0.8600
C14A—H14C	0.9600	N2—H2	0.8600
C14A—H14A	0.9600	S1—C12ⁱ	1.719 (4)
C14B—O4B	1.33 (2)	S2—C25ⁱⁱ	1.711 (4)

O1—C1—H1A	109.5	O5A—C15—O4A	97 (3)
O1—C1—H1B	109.5	O4B—C15—O4A	106.1 (13)
H1A—C1—H1B	109.5	O5A—C15—C16	126 (3)
O1—C1—H1C	109.5	O5B—C15—C16	116.8 (7)
H1A—C1—H1C	109.5	O4B—C15—C16	112.0 (8)
H1B—C1—H1C	109.5	O4A—C15—C16	132.5 (9)
O2—C2—O1	123.4 (5)	C15—C16—N2	111.0 (5)
O2—C2—C3	123.0 (5)	C15—C16—C17	115.6 (6)
O1—C2—C3	113.6 (4)	N2—C16—C17	110.9 (6)
N1—C3—C2	112.9 (4)	C15—C16—H16	106.2
N1—C3—C4	111.6 (4)	N2—C16—H16	106.2
C2—C3—C4	110.2 (4)	C17—C16—H16	106.2
N1—C3—H3	107.3	C18—C17—C16	113.2 (6)
C2—C3—H3	107.3	C18—C17—H17A	108.9
C4—C3—H3	107.3	C16—C17—H17A	108.9
C3—C4—C5	112.9 (4)	C18—C17—H17B	108.9
C3—C4—H4B	109.0	C16—C17—H17B	108.9
C5—C4—H4B	109.0	H17A—C17—H17B	107.7
C3—C4—H4A	109.0	C19—C18—C23	114.1 (7)
C5—C4—H4A	109.0	C19—C18—C17	122.4 (7)
H4B—C4—H4A	107.8	C23—C18—C17	123.2 (5)
C10—C5—C6	119.0 (5)	C18—C19—C20	124.2 (7)
C10—C5—C4	120.3 (4)	C18—C19—H19	117.9
C6—C5—C4	120.6 (4)	C20—C19—H19	117.9
C5—C6—C7	119.4 (5)	C21—C20—C19	119.1 (6)
C5—C6—H6	120.3	C21—C20—H20	120.4
C7—C6—H6	120.3	C19—C20—H20	120.4
C8—C7—C6	120.5 (5)	C20—C21—C22	120.2 (7)
C8—C7—H7	119.7	C20—C21—H21	119.9
C6—C7—H7	119.7	C22—C21—H21	119.9
C9—C8—C7	119.7 (5)	C23—C22—C21	119.0 (7)
C9—C8—H8	120.2	C23—C22—H22	120.5
C7—C8—H8	120.2	C21—C22—H22	120.5
C8—C9—C10	120.0 (5)	C22—C23—C18	123.2 (6)
C8—C9—H9	120.0	C22—C23—H23	118.4
C10—C9—H9	120.0	C18—C23—H23	118.4
C5—C10—C9	121.3 (4)	O6—C24—N2	123.0 (4)
C5—C10—H10	119.3	O6—C24—C25	118.7 (4)
C9—C10—H10	119.3	N2—C24—C25	118.3 (4)
O3—C11—N1	123.3 (4)	C26—C25—C24	133.0 (4)
O3—C11—C12	120.7 (4)	C26—C25—S2	111.7 (3)
N1—C11—C12	115.9 (4)	C24—C25—S2	115.4 (3)
C13—C12—C11	130.6 (4)	C25—C26—C26ⁱⁱ	112.3 (3)
C13—C12—S1	112.0 (3)	C25—C26—H26	123.8
C11—C12—S1	117.2 (3)	C26ⁱⁱ—C26—H26	123.8
C12—C13—C13ⁱ	112.9 (3)	C11—N1—C3	123.2 (4)
C12—C13—H13	123.6	C11—N1—H1	118.4
C13ⁱ—C13—H13	123.6	C3—N1—H1	118.4
O4A—C14A—H14B	109.5	C24—N2—C16	122.1 (4)
O4A—C14A—H14C	109.5	C24—N2—H2	119.0
H14B—C14A—H14C	109.5	C16—N2—H2	119.0
O4A—C14A—H14A	109.5	C2—O1—C1	116.6 (4)
H14B—C14A—H14A	109.5	C14A—O4A—C15	133.5 (17)
H14C—C14A—H14A	109.5	C15—O4B—C14B	111.0 (12)
O5A—C15—O5B	116 (2)	C12ⁱ—S1—C12	90.3 (3)
O5B—C15—O4B	131.1 (11)	C25ⁱⁱ—S2—C25	92.1 (3)

O2—C2—C3—N1	169.7 (4)	C17—C18—C19—C20	173.7 (6)
O1—C2—C3—N1	−9.4 (6)	C18—C19—C20—C21	−0.1 (10)
O2—C2—C3—C4	−64.8 (6)	C19—C20—C21—C22	−2.1 (9)
O1—C2—C3—C4	116.1 (4)	C20—C21—C22—C23	4.4 (9)
N1—C3—C4—C5	−71.2 (4)	C21—C22—C23—C18	−4.6 (10)
C2—C3—C4—C5	162.7 (4)	C19—C18—C23—C22	2.4 (9)
C3—C4—C5—C10	−90.3 (5)	C17—C18—C23—C22	−171.2 (6)
C3—C4—C5—C6	85.1 (6)	O6—C24—C25—C26	−177.5 (5)
C10—C5—C6—C7	−1.7 (9)	N2—C24—C25—C26	1.8 (8)
C4—C5—C6—C7	−177.2 (6)	O6—C24—C25—S2	3.2 (6)
C5—C6—C7—C8	2.2 (11)	N2—C24—C25—S2	−177.5 (4)
C6—C7—C8—C9	−2.4 (11)	C24—C25—C26—C26ⁱⁱ	−179.0 (5)
C7—C8—C9—C10	2.2 (10)	S2—C25—C26—C26ⁱⁱ	0.4 (8)
C6—C5—C10—C9	1.5 (8)	O3—C11—N1—C3	−13.2 (7)
C4—C5—C10—C9	177.0 (5)	C12—C11—N1—C3	167.1 (4)
C8—C9—C10—C5	−1.8 (9)	C2—C3—N1—C11	−95.6 (5)
O3—C11—C12—C13	168.5 (5)	C4—C3—N1—C11	139.6 (4)
N1—C11—C12—C13	−11.8 (8)	O6—C24—N2—C16	−4.5 (8)
O3—C11—C12—S1	−5.5 (6)	C25—C24—N2—C16	176.3 (5)
N1—C11—C12—S1	174.2 (3)	C15—C16—N2—C24	−99.5 (6)
C11—C12—C13—C13ⁱ	−175.3 (5)	C17—C16—N2—C24	130.5 (6)
S1—C12—C13—C13ⁱ	−1.0 (8)	O2—C2—O1—C1	−3.0 (8)
O5A—C15—C16—N2	18 (3)	C3—C2—O1—C1	176.1 (5)
O5B—C15—C16—N2	−153.2 (7)	O5A—C15—O4A—C14A	−6 (3)
O4B—C15—C16—N2	30.1 (11)	O5B—C15—O4A—C14A	122 (3)
O4A—C15—C16—N2	171.0 (12)	O4B—C15—O4A—C14A	−22 (3)
O5A—C15—C16—C17	145 (3)	C16—C15—O4A—C14A	−164.4 (18)
O5B—C15—C16—C17	−25.7 (9)	O5A—C15—O4B—C14B	−41 (11)
O4B—C15—C16—C17	157.6 (10)	O5B—C15—O4B—C14B	−3 (2)
O4A—C15—C16—C17	−61.5 (14)	O4A—C15—O4B—C14B	22.3 (18)
C15—C16—C17—C18	161.2 (5)	C16—C15—O4B—C14B	173.4 (12)
N2—C16—C17—C18	−71.2 (7)	C13—C12—S1—C12ⁱ	0.4 (3)
C16—C17—C18—C19	−96.0 (7)	C11—C12—S1—C12ⁱ	175.5 (5)
C16—C17—C18—C23	77.1 (8)	C26—C25—S2—C25ⁱⁱ	−0.1 (3)
C23—C18—C19—C20	0.0 (9)	C24—C25—S2—C25ⁱⁱ	179.3 (5)

Symmetry codes: (i) −x+1, −y+1, z; (ii) −x+2, −y+1, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O6	0.86	2.01	2.853 (5)	164
N2—H2···O3ⁱⁱⁱ	0.86	2.10	2.803 (5)	139

Symmetry code: (iii) x, y, z−1.

Experimental details

Crystal data
Chemical formula	C₂₆H₂₆N₂O₆S
M_r	494.56
Crystal system, space group	Orthorhombic, P2₁2₁2
Temperature (K)	120
a, b, c (Å)	9.0769 (3), 29.6371 (7), 9.3767 (2)
V (Å³)	2522.45 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.17
Crystal size (mm)	0.36 × 0.24 × 0.10

Data collection
Diffractometer	Oxford Diffraction Xcalibur Eos Gemini
Absorption correction	Multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009)
T_min, T_max	0.867, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	6802, 4233, 3315
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.068, 0.187, 1.10
No. of reflections	4233
No. of parameters	288
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.90, −0.70
Absolute structure	Flack (1983), 1669 Friedel pairs
Absolute structure parameter	0.00 (18)

Computer programs: CrysAlis PRO CCD (Oxford Diffraction, 2009), CrysAlis PRO RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O6	0.86	2.01	2.853 (5)	164.4
N2—H2···O3ⁱ	0.86	2.10	2.803 (5)	138.9

Symmetry code: (i) x, y, z−1.

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

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals 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., Ji, M.-W., Lu, P., Sun, G.-X. & Xu, W.-F. (2010). Acta Cryst. E66, o148. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 66| Part 9| September 2010| Page o2385

https://doi.org/10.1107/S1600536810033210

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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

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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