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Acta Crystallogr Sect E Struct Rep Online. 2010 October 1; 66(Pt 10): o2489.
Published online 2010 September 4. doi:  10.1107/S1600536810034410
PMCID: PMC2983431

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

Abstract

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 C 2 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 [triangle]). For the synthesis of the title compound, see: Moriuchi et al. (2006 [triangle]). For the structure of the unsolvated mol­ecule, see: Xia et al. (2010 [triangle]).

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Object name is e-66-o2489-scheme1.jpg

Experimental

Crystal data

  • C26H26N2O6S·C4H8O
  • M r = 566.65
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2489-efi1.jpg
  • 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 [triangle]) 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[F 2 > 2σ(F 2)] = 0.047
  • wR(F 2) = 0.094
  • S = 0.91
  • 5081 reflections
  • 363 parameters
  • H-atom parameters constrained
  • Δρmax = 0.19 e Å−3
  • Δρmin = −0.21 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 1964 Friedel pairs
  • Flack parameter: −0.05 (9)

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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.

supplementary crystallographic information

Comment

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).

Experimental

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.

Refinement

All H atoms were placed in idealized positions and refined using a riding model, with N—H = 0.86 Å, and C—H = 0.93–0.98 Å, and with Uiso(H) = 1.2–1.5Ueq(carrier atom). Absolute configuration was assigned by refinement of the Flack parameter (Flack, 1983), based on 1964 measured Friedel pairs.

Figures

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

Crystal data

C26H26N2O6S·C4H8OF(000) = 1200
Mr = 566.65Dx = 1.254 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 3062 reflections
a = 8.3041 (3) Åθ = 3.0–28.8°
b = 12.1810 (4) ŵ = 0.16 mm1
c = 29.6787 (11) ÅT = 293 K
V = 3002.06 (17) Å3Block, colourless
Z = 40.40 × 0.21 × 0.08 mm

Data collection

Oxford Xcalibur (Eos) CCD detector diffractometer5081 independent reflections
Radiation source: Enhance (Mo) X-ray Source3167 reflections with I > 2σ(I)
graphiteRint = 0.022
Detector resolution: 16.0355 pixels mm-1θmax = 25.3°, θmin = 3.0°
ω scansh = −9→9
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009)k = −14→12
Tmin = 0.941, Tmax = 0.988l = −15→35
7782 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047H-atom parameters constrained
wR(F2) = 0.094w = 1/[σ2(Fo2) + (0.0458P)2] where P = (Fo2 + 2Fc2)/3
S = 0.91(Δ/σ)max < 0.001
5081 reflectionsΔρmax = 0.19 e Å3
363 parametersΔρmin = −0.20 e Å3
0 restraintsAbsolute structure: Flack (1983), 1964 Friedel pairs
0 constraintsFlack parameter: −0.05 (9)
Primary atom site location: structure-invariant direct methods

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

xyzUiso*/Ueq
C10.7362 (4)−0.1856 (4)−0.38825 (15)0.0993 (14)
H1A0.7425−0.2168−0.35860.149*
H1B0.7790−0.1124−0.38780.149*
H1C0.7976−0.2297−0.40880.149*
C20.4695 (4)−0.1250 (3)−0.37793 (13)0.0615 (9)
C30.2978 (3)−0.1273 (2)−0.39603 (10)0.0476 (8)
H30.2785−0.2003−0.40890.057*
C40.2776 (4)−0.0426 (2)−0.43389 (11)0.0555 (8)
H4A0.29110.0305−0.42150.067*
H4B0.3615−0.0538−0.45620.067*
C50.1160 (4)−0.0496 (2)−0.45669 (10)0.0466 (8)
C60.0864 (4)−0.1295 (3)−0.48868 (12)0.0638 (9)
H60.1673−0.1793−0.49600.077*
C7−0.0602 (5)−0.1369 (3)−0.50983 (13)0.0782 (11)
H7−0.0772−0.1897−0.53190.094*
C8−0.1798 (5)−0.0671 (4)−0.49844 (15)0.0794 (12)
H8−0.2804−0.0741−0.51190.095*
C9−0.1543 (5)0.0131 (3)−0.46754 (16)0.0804 (12)
H9−0.23610.0624−0.46060.097*
C10−0.0064 (4)0.0216 (2)−0.44637 (11)0.0628 (9)
H100.01020.0761−0.42490.075*
C110.1316 (3)−0.1966 (3)−0.33570 (10)0.0476 (7)
C120.0384 (3)−0.1773 (2)−0.29456 (10)0.0428 (7)
C13−0.0220 (4)−0.0850 (2)−0.27630 (10)0.0588 (9)
H13−0.0123−0.0160−0.28940.071*
C14−0.1017 (4)−0.1042 (2)−0.23495 (12)0.0609 (9)
H14−0.1489−0.0490−0.21780.073*
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−0.8026−0.2648−0.12940.166*
H17B−0.7452−0.3834−0.14220.166*
H17C−0.7846−0.2983−0.18020.166*
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)
H19−0.2553−0.2970−0.10340.054*
C20−0.3044 (3)−0.1424 (2)−0.08026 (11)0.0543 (9)
H20B−0.3664−0.0799−0.09060.065*
H20A−0.3466−0.1643−0.05110.065*
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)
H22−0.0732−0.2182−0.02730.082*
C230.1266 (6)−0.1322 (4)−0.04062 (16)0.0960 (14)
H230.1916−0.1688−0.02000.115*
C240.1900 (6)−0.0506 (5)−0.0661 (2)0.1118 (18)
H240.2977−0.0309−0.06340.134*
C250.0910 (7)0.0024 (4)−0.0962 (2)0.1108 (16)
H250.13270.0587−0.11390.133*
C26−0.0682 (5)−0.0260 (3)−0.10075 (14)0.0785 (11)
H26−0.13270.0111−0.12140.094*
C27−0.5480 (9)−0.0480 (5)−0.2287 (2)0.210 (4)
H27A−0.4867−0.0942−0.24900.252*
H27B−0.6468−0.0857−0.22070.252*
C28−0.5824 (9)0.0546 (6)−0.2491 (2)0.184 (3)
H28B−0.69610.0597−0.25630.221*
H28A−0.52110.0629−0.27670.221*
C29−0.5388 (8)0.1382 (5)−0.2175 (2)0.170 (3)
H29B−0.62840.1875−0.21210.204*
H29A−0.44800.1806−0.22850.204*
C30−0.4949 (7)0.0780 (4)−0.17561 (19)0.1219 (16)
H30A−0.40480.1133−0.16070.146*
H30B−0.58540.0758−0.15500.146*
N10.1852 (3)−0.11168 (19)−0.35934 (8)0.0479 (6)
H10.1527−0.0466−0.35280.057*
N2−0.2705 (2)−0.20642 (19)−0.15812 (8)0.0430 (6)
H2−0.3083−0.1474−0.17000.052*
O10.5682 (3)−0.1824 (2)−0.40280 (8)0.0745 (7)
O20.5104 (3)−0.0779 (3)−0.34523 (11)0.1289 (13)
O30.1599 (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)

U11U22U33U12U13U23
C10.054 (2)0.142 (4)0.102 (3)0.014 (2)0.001 (2)0.028 (3)
C20.060 (2)0.079 (2)0.045 (2)−0.0056 (19)0.004 (2)−0.0055 (19)
C30.0561 (19)0.0494 (17)0.037 (2)−0.0002 (15)0.0048 (17)−0.0052 (16)
C40.064 (2)0.0541 (19)0.048 (2)−0.0067 (16)0.0060 (19)−0.0004 (17)
C50.0574 (18)0.0435 (17)0.039 (2)−0.0019 (16)0.0095 (17)0.0004 (16)
C60.073 (2)0.062 (2)0.056 (2)0.0068 (18)0.002 (2)−0.015 (2)
C70.090 (3)0.081 (3)0.064 (3)−0.006 (2)−0.011 (2)−0.014 (2)
C80.077 (3)0.083 (3)0.079 (3)−0.003 (2)−0.019 (3)0.016 (3)
C90.075 (3)0.073 (3)0.093 (4)0.020 (2)0.006 (3)0.020 (3)
C100.080 (2)0.0543 (18)0.054 (2)0.001 (2)0.004 (2)−0.0020 (16)
C110.0565 (17)0.0441 (18)0.042 (2)0.0000 (16)0.0048 (16)−0.0058 (16)
C120.0481 (16)0.0448 (16)0.0357 (18)−0.0063 (13)0.0065 (15)−0.0025 (14)
C130.083 (2)0.0396 (16)0.053 (2)−0.0001 (17)0.022 (2)0.0063 (15)
C140.078 (2)0.0443 (18)0.061 (2)0.0057 (15)0.032 (2)−0.0004 (17)
C150.0430 (14)0.0451 (17)0.0396 (19)−0.0047 (13)0.0040 (14)−0.0019 (15)
C160.0402 (16)0.0413 (17)0.042 (2)−0.0075 (13)−0.0025 (15)−0.0023 (15)
C170.058 (2)0.169 (4)0.106 (4)−0.041 (3)−0.019 (2)0.003 (3)
C180.0449 (17)0.0638 (18)0.053 (2)0.0000 (18)0.006 (2)0.0113 (18)
C190.0463 (17)0.0491 (17)0.0394 (19)0.0077 (14)0.0069 (16)0.0049 (15)
C200.059 (2)0.064 (2)0.041 (2)0.0049 (16)0.0100 (17)−0.0013 (17)
C210.063 (2)0.052 (2)0.044 (2)−0.0059 (17)0.0036 (19)−0.0103 (17)
C220.070 (3)0.075 (2)0.062 (3)0.0000 (19)0.000 (2)0.004 (2)
C230.080 (3)0.123 (4)0.085 (4)−0.001 (3)−0.019 (3)−0.014 (3)
C240.070 (3)0.142 (5)0.123 (5)−0.022 (3)−0.009 (3)−0.044 (4)
C250.111 (4)0.107 (4)0.115 (5)−0.058 (3)0.026 (4)−0.003 (3)
C260.090 (3)0.070 (2)0.076 (3)−0.021 (2)0.004 (2)0.009 (2)
C270.296 (9)0.128 (4)0.205 (8)0.092 (5)−0.165 (8)−0.053 (5)
C280.273 (8)0.179 (6)0.100 (5)0.115 (6)−0.059 (5)−0.021 (5)
C290.221 (7)0.108 (4)0.183 (7)0.041 (4)−0.082 (6)0.015 (5)
C300.136 (4)0.105 (3)0.125 (4)0.033 (3)−0.008 (4)−0.011 (3)
N10.0621 (15)0.0417 (14)0.0399 (17)0.0044 (12)0.0133 (14)−0.0017 (12)
N20.0471 (13)0.0418 (12)0.0401 (15)0.0052 (12)0.0075 (12)0.0059 (13)
O10.0563 (14)0.0945 (17)0.0728 (18)0.0055 (13)0.0091 (13)−0.0053 (15)
O20.0844 (19)0.212 (3)0.090 (2)0.004 (2)−0.0221 (19)−0.072 (2)
O30.141 (2)0.0481 (14)0.0839 (19)−0.0028 (15)0.0556 (17)−0.0047 (14)
O40.0709 (13)0.0386 (11)0.0568 (16)0.0086 (10)0.0112 (12)0.0071 (11)
O50.0672 (16)0.151 (2)0.082 (2)−0.0221 (15)0.0101 (14)0.047 (2)
O60.0554 (13)0.128 (2)0.0623 (17)−0.0274 (13)−0.0090 (13)0.0150 (16)
O70.161 (3)0.0830 (19)0.110 (3)0.054 (2)−0.056 (2)−0.0078 (18)
S10.0711 (5)0.0404 (4)0.0516 (5)0.0027 (4)0.0181 (5)0.0008 (4)

Geometric parameters (Å, °)

C1—O11.461 (4)C17—H17A0.9600
C1—H1A0.9600C17—H17B0.9600
C1—H1B0.9600C17—H17C0.9600
C1—H1C0.9600C18—O51.188 (3)
C2—O21.178 (4)C18—O61.299 (4)
C2—O11.306 (4)C18—C191.509 (4)
C2—C31.524 (4)C19—N21.446 (3)
C3—N11.448 (3)C19—C201.533 (4)
C3—C41.535 (4)C19—H190.9800
C3—H30.9800C20—C211.491 (4)
C4—C51.506 (4)C20—H20B0.9700
C4—H4A0.9700C20—H20A0.9700
C4—H4B0.9700C21—C261.377 (4)
C5—C101.371 (4)C21—C221.378 (4)
C5—C61.382 (4)C22—C231.374 (5)
C6—C71.373 (5)C22—H220.9300
C6—H60.9300C23—C241.357 (6)
C7—C81.350 (5)C23—H230.9300
C7—H70.9300C24—C251.374 (6)
C8—C91.357 (5)C24—H240.9300
C8—H80.9300C25—C261.373 (5)
C9—C101.383 (5)C25—H250.9300
C9—H90.9300C26—H260.9300
C10—H100.9300C27—C281.417 (7)
C11—O31.229 (3)C27—O71.445 (6)
C11—N11.327 (3)C27—H27A0.9700
C11—C121.465 (4)C27—H27B0.9700
C12—C131.345 (4)C28—C291.430 (7)
C12—S11.711 (3)C28—H28B0.9700
C13—C141.414 (4)C28—H28A0.9700
C13—H130.9300C29—C301.489 (6)
C14—C151.342 (4)C29—H29B0.9700
C14—H140.9300C29—H29A0.9700
C15—C161.491 (4)C30—O71.333 (4)
C15—S11.716 (3)C30—H30A0.9700
C16—O41.232 (3)C30—H30B0.9700
C16—N21.328 (3)N1—H10.8600
C17—O61.465 (4)N2—H20.8600
O1—C1—H1A109.5O6—C18—C19113.8 (3)
O1—C1—H1B109.5N2—C19—C18114.4 (3)
H1A—C1—H1B109.5N2—C19—C20110.9 (2)
O1—C1—H1C109.5C18—C19—C20110.7 (2)
H1A—C1—H1C109.5N2—C19—H19106.8
H1B—C1—H1C109.5C18—C19—H19106.8
O2—C2—O1123.1 (3)C20—C19—H19106.8
O2—C2—C3124.7 (3)C21—C20—C19112.6 (2)
O1—C2—C3112.2 (3)C21—C20—H20B109.1
N1—C3—C2109.7 (3)C19—C20—H20B109.1
N1—C3—C4113.1 (2)C21—C20—H20A109.1
C2—C3—C4110.3 (2)C19—C20—H20A109.1
N1—C3—H3107.9H20B—C20—H20A107.8
C2—C3—H3107.9C26—C21—C22117.8 (3)
C4—C3—H3107.9C26—C21—C20120.9 (3)
C5—C4—C3112.8 (2)C22—C21—C20121.3 (3)
C5—C4—H4A109.0C23—C22—C21121.3 (4)
C3—C4—H4A109.0C23—C22—H22119.3
C5—C4—H4B109.0C21—C22—H22119.3
C3—C4—H4B109.0C24—C23—C22120.8 (4)
H4A—C4—H4B107.8C24—C23—H23119.6
C10—C5—C6117.9 (3)C22—C23—H23119.6
C10—C5—C4121.7 (3)C23—C24—C25118.3 (4)
C6—C5—C4120.5 (3)C23—C24—H24120.8
C7—C6—C5121.2 (3)C25—C24—H24120.8
C7—C6—H6119.4C26—C25—C24121.5 (5)
C5—C6—H6119.4C26—C25—H25119.3
C8—C7—C6119.8 (4)C24—C25—H25119.3
C8—C7—H7120.1C25—C26—C21120.3 (4)
C6—C7—H7120.1C25—C26—H26119.8
C7—C8—C9120.5 (4)C21—C26—H26119.8
C7—C8—H8119.7C28—C27—O7105.8 (5)
C9—C8—H8119.7C28—C27—H27A110.6
C8—C9—C10119.9 (4)O7—C27—H27A110.6
C8—C9—H9120.0C28—C27—H27B110.6
C10—C9—H9120.0O7—C27—H27B110.6
C5—C10—C9120.7 (3)H27A—C27—H27B108.7
C5—C10—H10119.7C27—C28—C29107.3 (5)
C9—C10—H10119.7C27—C28—H28B110.3
O3—C11—N1121.2 (3)C29—C28—H28B110.3
O3—C11—C12119.3 (3)C27—C28—H28A110.3
N1—C11—C12119.5 (3)C29—C28—H28A110.3
C13—C12—C11131.8 (3)H28B—C28—H28A108.5
C13—C12—S1111.4 (2)C28—C29—C30105.0 (5)
C11—C12—S1116.8 (2)C28—C29—H29B110.8
C12—C13—C14112.7 (3)C30—C29—H29B110.8
C12—C13—H13123.7C28—C29—H29A110.8
C14—C13—H13123.7C30—C29—H29A110.8
C15—C14—C13113.1 (3)H29B—C29—H29A108.8
C15—C14—H14123.4O7—C30—C29105.7 (4)
C13—C14—H14123.4O7—C30—H30A110.6
C14—C15—C16130.6 (3)C29—C30—H30A110.6
C14—C15—S1111.1 (2)O7—C30—H30B110.6
C16—C15—S1118.1 (2)C29—C30—H30B110.6
O4—C16—N2123.9 (3)H30A—C30—H30B108.7
O4—C16—C15121.2 (3)C11—N1—C3120.8 (2)
N2—C16—C15114.8 (2)C11—N1—H1119.6
O6—C17—H17A109.5C3—N1—H1119.6
O6—C17—H17B109.5C16—N2—C19123.0 (2)
H17A—C17—H17B109.5C16—N2—H2118.5
O6—C17—H17C109.5C19—N2—H2118.5
H17A—C17—H17C109.5C2—O1—C1116.5 (3)
H17B—C17—H17C109.5C18—O6—C17116.6 (3)
O5—C18—O6124.1 (3)C30—O7—C27107.6 (4)
O5—C18—C19122.1 (3)C12—S1—C1591.70 (14)
O2—C2—C3—N1−27.1 (5)N2—C19—C20—C21−61.3 (3)
O1—C2—C3—N1152.6 (3)C18—C19—C20—C21170.6 (3)
O2—C2—C3—C498.1 (4)C19—C20—C21—C2693.0 (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—C230.3 (5)
C2—C3—C4—C5173.6 (3)C20—C21—C22—C23178.8 (3)
C3—C4—C5—C10100.2 (3)C21—C22—C23—C24−0.4 (6)
C3—C4—C5—C6−79.2 (4)C22—C23—C24—C250.4 (7)
C10—C5—C6—C70.7 (5)C23—C24—C25—C26−0.2 (8)
C4—C5—C6—C7−179.9 (3)C24—C25—C26—C210.0 (7)
C5—C6—C7—C8−2.0 (6)C22—C21—C26—C25−0.1 (5)
C6—C7—C8—C92.7 (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—O723.0 (7)
C8—C9—C10—C50.9 (5)O3—C11—N1—C3−8.9 (4)
O3—C11—C12—C13−173.0 (3)C12—C11—N1—C3170.4 (2)
N1—C11—C12—C137.7 (5)C2—C3—N1—C11−87.8 (3)
O3—C11—C12—S18.6 (4)C4—C3—N1—C11148.6 (3)
N1—C11—C12—S1−170.8 (2)O4—C16—N2—C199.1 (4)
C11—C12—C13—C14−178.4 (3)C15—C16—N2—C19−170.2 (2)
S1—C12—C13—C140.1 (3)C18—C19—N2—C16−107.0 (3)
C12—C13—C14—C15−0.8 (4)C20—C19—N2—C16127.0 (3)
C13—C14—C15—C16176.3 (3)O2—C2—O1—C1−0.3 (5)
C13—C14—C15—S11.2 (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—O415.0 (3)C19—C18—O6—C17−178.2 (3)
C14—C15—C16—N219.5 (4)C29—C30—O7—C27−30.3 (6)
S1—C15—C16—N2−165.68 (19)C28—C27—O7—C3026.6 (7)
O5—C18—C19—N2173.3 (3)C13—C12—S1—C150.5 (2)
O6—C18—C19—N2−8.6 (4)C11—C12—S1—C15179.2 (2)
O5—C18—C19—C20−60.6 (4)C14—C15—S1—C12−1.0 (2)
O6—C18—C19—C20117.5 (3)C16—C15—S1—C12−176.8 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2···O70.862.022.859 (3)164

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BH2306).

References

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