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Acta Crystallogr Sect E Struct Rep Online. 2010 September 1; 66(Pt 9): o2385.
Published online 2010 August 25. doi:  10.1107/S1600536810033210
PMCID: PMC3007902

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

Abstract

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 [triangle]).

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Object name is e-66-o2385-scheme1.jpg

Experimental

Crystal data

  • C26H26N2O6S
  • M r = 494.56
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2385-efi1.jpg
  • 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 [triangle]) 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[F 2 > 2σ(F 2)] = 0.068
  • wR(F 2) = 0.187
  • S = 1.10
  • 4233 reflections
  • 288 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.90 e Å−3
  • Δρmin = −0.70 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 1669 Friedel pairs
  • Flack parameter: 0.00 (18)

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: ORTEP-3 for Windows (Farrugia, 1997 [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/S1600536810033210/xu5003sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810033210/xu5003Isup2.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 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.

Experimental

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.

Refinement

All H atoms were placed in idealized positions and refined using a riding model, with N–H = 0.86 Å, C–H = 0.93–0.98 Å and with Uiso(H) = 1.2–1.5 Ueq(C,N).

Figures

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

Crystal data

C26H26N2O6SF(000) = 1040
Mr = 494.56Dx = 1.302 Mg m3
Orthorhombic, P21212Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2 2abCell parameters from 4047 reflections
a = 9.0769 (3) Åθ = 3.4–25.3°
b = 29.6371 (7) ŵ = 0.17 mm1
c = 9.3767 (2) ÅT = 120 K
V = 2522.45 (12) Å3Block, colourless
Z = 40.36 × 0.24 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer4233 independent reflections
Radiation source: Enhance (Mo) X-ray Source3315 reflections with I > 2σ(I)
graphiteRint = 0.051
Detector resolution: 16.0355 pixels mm-1θmax = 25.0°, θmin = 3.4°
ω scansh = −6→10
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009)k = −28→35
Tmin = 0.867, Tmax = 1.000l = −7→11
6802 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)] = 0.068H-atom parameters constrained
wR(F2) = 0.187w = 1/[σ2(Fo2) + (0.1124P)2 + 0.8367P] where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max < 0.001
4233 reflectionsΔρmax = 0.90 e Å3
288 parametersΔρmin = −0.70 e Å3
1 restraintAbsolute structure: Flack (1983), 1669 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.00 (18)

Special details

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)

xyzUiso*/UeqOcc. (<1)
C10.3969 (8)0.6948 (2)0.3748 (8)0.0676 (18)
H1A0.31120.67710.35290.101*
H1B0.42590.71170.29200.101*
H1C0.37450.71530.45120.101*
C20.6263 (6)0.68418 (15)0.4908 (5)0.0361 (11)
C30.7416 (5)0.65073 (14)0.5404 (5)0.0336 (11)
H30.75450.65510.64320.040*
C40.8884 (6)0.66076 (14)0.4700 (5)0.0338 (11)
H4B0.90360.69320.46850.041*
H4A0.88550.65030.37200.041*
C51.0183 (6)0.63839 (14)0.5462 (4)0.0325 (10)
C61.0574 (6)0.59423 (18)0.5155 (7)0.0529 (15)
H61.00760.57820.44510.063*
C71.1729 (8)0.5739 (2)0.5915 (8)0.069 (2)
H71.20170.54460.56910.083*
C81.2438 (6)0.59686 (19)0.6990 (7)0.0549 (15)
H81.31770.58280.75140.066*
C91.2052 (7)0.64021 (18)0.7282 (6)0.0521 (14)
H91.25510.65620.79850.063*
C101.0909 (6)0.66065 (16)0.6527 (5)0.0433 (13)
H101.06350.69000.67530.052*
C110.6350 (5)0.57915 (14)0.6197 (4)0.0281 (10)
C120.5668 (5)0.53566 (13)0.5707 (4)0.0281 (10)
C130.5371 (6)0.52036 (15)0.4374 (4)0.0352 (12)
H130.56390.53570.35480.042*
C14A0.207 (2)0.6027 (7)0.130 (2)0.047 (4)0.275 (12)
H14B0.17400.59000.04110.070*0.275 (12)
H14C0.13800.62500.16160.070*0.275 (12)
H14A0.21470.57920.19990.070*0.275 (12)
C14B0.3361 (17)0.5483 (4)0.091 (2)0.123 (6)0.725 (12)
H14E0.29380.5485−0.00260.184*0.725 (12)
H14F0.27930.56740.15290.184*0.725 (12)
H14D0.33590.51810.12800.184*0.725 (12)
C150.4767 (9)0.6062 (2)0.0647 (6)0.0674 (7)
C160.6251 (9)0.6243 (2)0.0738 (7)0.0674 (7)
H160.64380.62990.17520.081*
C170.6498 (9)0.6692 (2)−0.0017 (7)0.0674 (7)
H17A0.65820.6638−0.10340.081*
H17B0.56460.68830.01370.081*
C180.7826 (9)0.6931 (2)0.0477 (6)0.0674 (7)
C190.7774 (9)0.7261 (2)0.1503 (6)0.0674 (7)
H190.68530.73540.18220.081*
C200.9003 (9)0.7463 (2)0.2091 (7)0.0674 (7)
H200.89020.76860.27830.081*
C211.0373 (9)0.7331 (2)0.1643 (6)0.0674 (7)
H211.12070.74720.20080.081*
C221.0519 (9)0.6990 (2)0.0649 (6)0.0674 (7)
H221.14480.68860.03890.081*
C230.9280 (9)0.6808 (2)0.0052 (7)0.0674 (7)
H230.93910.6594−0.06660.081*
C240.8109 (6)0.56624 (14)0.1212 (4)0.0287 (10)
C250.9113 (5)0.53145 (14)0.0658 (4)0.0284 (10)
C260.9493 (6)0.51816 (16)−0.0702 (4)0.0395 (13)
H260.91240.5315−0.15260.047*
N10.6976 (4)0.60424 (11)0.5186 (4)0.0276 (8)
H10.71270.59230.43640.033*
N20.7346 (5)0.59066 (12)0.0283 (4)0.0378 (10)
H20.74970.5867−0.06140.045*
O10.5160 (5)0.66529 (11)0.4175 (4)0.0507 (10)
O20.6327 (4)0.72365 (11)0.5165 (5)0.0555 (11)
O30.6321 (4)0.59001 (10)0.7462 (3)0.0403 (9)
O4A0.342 (2)0.6223 (6)0.111 (2)0.047 (4)0.275 (12)
O4B0.4741 (16)0.5635 (4)0.0848 (17)0.078 (3)0.725 (12)
O5A0.443 (6)0.5668 (8)0.057 (5)0.078 (3)0.275 (12)
O5B0.3754 (8)0.6338 (3)0.0463 (11)0.070 (2)0.725 (12)
O60.8024 (4)0.57171 (10)0.2509 (3)0.0349 (8)
S10.50000.50000.70005 (14)0.0268 (4)
S21.00000.50000.19249 (14)0.0265 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.063 (4)0.068 (4)0.072 (4)0.008 (3)−0.025 (4)−0.005 (3)
C20.042 (3)0.030 (2)0.037 (2)0.007 (2)0.012 (2)0.0014 (19)
C30.041 (3)0.033 (2)0.027 (2)−0.002 (2)−0.002 (2)−0.0013 (18)
C40.050 (3)0.029 (2)0.022 (2)−0.007 (2)0.000 (2)−0.0004 (17)
C50.033 (3)0.034 (2)0.030 (2)−0.001 (2)0.004 (2)−0.0016 (18)
C60.048 (3)0.051 (3)0.059 (3)0.006 (3)−0.013 (3)−0.030 (3)
C70.073 (4)0.055 (3)0.081 (4)0.031 (3)−0.026 (4)−0.038 (3)
C80.046 (3)0.059 (3)0.060 (3)0.018 (3)−0.018 (3)−0.013 (3)
C90.054 (4)0.052 (3)0.051 (3)0.004 (3)−0.009 (3)−0.020 (3)
C100.053 (3)0.033 (2)0.044 (3)0.003 (2)−0.009 (3)−0.008 (2)
C110.035 (3)0.031 (2)0.018 (2)0.004 (2)−0.0055 (19)0.0008 (16)
C120.041 (3)0.027 (2)0.0163 (19)0.002 (2)0.0030 (19)0.0048 (16)
C130.056 (4)0.035 (2)0.015 (2)−0.012 (2)−0.005 (2)0.0033 (17)
C14A0.034 (7)0.053 (8)0.053 (8)−0.013 (5)0.010 (6)0.002 (6)
C14B0.110 (12)0.068 (7)0.191 (16)−0.018 (7)−0.066 (11)0.014 (8)
C150.0996 (18)0.0573 (12)0.0455 (11)0.0261 (13)0.0108 (12)−0.0013 (9)
C160.0996 (18)0.0573 (12)0.0455 (11)0.0261 (13)0.0108 (12)−0.0013 (9)
C170.0996 (18)0.0573 (12)0.0455 (11)0.0261 (13)0.0108 (12)−0.0013 (9)
C180.0996 (18)0.0573 (12)0.0455 (11)0.0261 (13)0.0108 (12)−0.0013 (9)
C190.0996 (18)0.0573 (12)0.0455 (11)0.0261 (13)0.0108 (12)−0.0013 (9)
C200.0996 (18)0.0573 (12)0.0455 (11)0.0261 (13)0.0108 (12)−0.0013 (9)
C210.0996 (18)0.0573 (12)0.0455 (11)0.0261 (13)0.0108 (12)−0.0013 (9)
C220.0996 (18)0.0573 (12)0.0455 (11)0.0261 (13)0.0108 (12)−0.0013 (9)
C230.0996 (18)0.0573 (12)0.0455 (11)0.0261 (13)0.0108 (12)−0.0013 (9)
C240.040 (3)0.026 (2)0.020 (2)−0.002 (2)0.000 (2)−0.0021 (17)
C250.039 (3)0.024 (2)0.022 (2)−0.0018 (19)0.000 (2)0.0001 (16)
C260.069 (4)0.036 (2)0.013 (2)0.008 (2)−0.002 (2)0.0005 (16)
N10.044 (2)0.0221 (16)0.0167 (16)−0.0009 (17)−0.0006 (17)−0.0027 (14)
N20.065 (3)0.0338 (19)0.0141 (16)0.018 (2)−0.0050 (19)−0.0061 (14)
O10.054 (2)0.0389 (18)0.059 (2)0.0089 (18)−0.026 (2)−0.0115 (16)
O20.057 (3)0.0316 (19)0.078 (3)0.0055 (18)−0.012 (2)−0.0154 (17)
O30.066 (2)0.0395 (17)0.0156 (15)−0.0111 (17)−0.0077 (16)−0.0038 (13)
O4A0.034 (7)0.053 (8)0.053 (8)−0.013 (5)0.010 (6)0.002 (6)
O4B0.047 (8)0.115 (4)0.072 (8)0.011 (4)−0.005 (4)0.048 (4)
O5A0.047 (8)0.115 (4)0.072 (8)0.011 (4)−0.005 (4)0.048 (4)
O5B0.041 (4)0.070 (5)0.100 (6)0.020 (4)−0.026 (4)−0.014 (4)
O60.049 (2)0.0383 (16)0.0170 (15)0.0106 (16)−0.0037 (14)−0.0017 (12)
S10.0425 (9)0.0263 (7)0.0118 (6)0.0010 (7)0.0000.000
S20.0384 (8)0.0268 (7)0.0144 (6)0.0011 (7)0.0000.000

Geometric parameters (Å, °)

C1—O11.447 (7)C14B—H14E0.9600
C1—H1A0.9600C14B—H14F0.9600
C1—H1B0.9600C14B—H14D0.9600
C1—H1C0.9600C15—O5A1.21 (2)
C2—O21.196 (5)C15—O5B1.243 (9)
C2—O11.337 (6)C15—O4B1.280 (12)
C2—C31.515 (7)C15—O4A1.38 (2)
C3—N11.449 (6)C15—C161.453 (11)
C3—C41.516 (7)C16—N21.471 (7)
C3—H30.9800C16—C171.523 (9)
C4—C51.530 (7)C16—H160.9800
C4—H4B0.9700C17—C181.472 (10)
C4—H4A0.9700C17—H17A0.9700
C5—C101.366 (7)C17—H17B0.9700
C5—C61.386 (7)C18—C191.373 (8)
C6—C71.404 (9)C18—C231.426 (10)
C6—H60.9300C19—C201.381 (10)
C7—C81.376 (8)C19—H190.9300
C7—H70.9300C20—C211.369 (10)
C8—C91.360 (8)C20—H200.9300
C8—H80.9300C21—C221.381 (9)
C9—C101.395 (8)C21—H210.9300
C9—H90.9300C22—C231.367 (10)
C10—H100.9300C22—H220.9300
C11—O31.229 (5)C23—H230.9300
C11—N11.332 (6)C24—O61.229 (5)
C11—C121.502 (6)C24—N21.328 (6)
C12—C131.357 (6)C24—C251.471 (6)
C12—S11.719 (4)C25—C261.378 (6)
C13—C13i1.383 (9)C25—S21.711 (4)
C13—H130.9300C26—C26ii1.417 (10)
C14A—O4A1.37 (3)C26—H260.9300
C14A—H14B0.9600N1—H10.8600
C14A—H14C0.9600N2—H20.8600
C14A—H14A0.9600S1—C12i1.719 (4)
C14B—O4B1.33 (2)S2—C25ii1.711 (4)
O1—C1—H1A109.5O5A—C15—O4A97 (3)
O1—C1—H1B109.5O4B—C15—O4A106.1 (13)
H1A—C1—H1B109.5O5A—C15—C16126 (3)
O1—C1—H1C109.5O5B—C15—C16116.8 (7)
H1A—C1—H1C109.5O4B—C15—C16112.0 (8)
H1B—C1—H1C109.5O4A—C15—C16132.5 (9)
O2—C2—O1123.4 (5)C15—C16—N2111.0 (5)
O2—C2—C3123.0 (5)C15—C16—C17115.6 (6)
O1—C2—C3113.6 (4)N2—C16—C17110.9 (6)
N1—C3—C2112.9 (4)C15—C16—H16106.2
N1—C3—C4111.6 (4)N2—C16—H16106.2
C2—C3—C4110.2 (4)C17—C16—H16106.2
N1—C3—H3107.3C18—C17—C16113.2 (6)
C2—C3—H3107.3C18—C17—H17A108.9
C4—C3—H3107.3C16—C17—H17A108.9
C3—C4—C5112.9 (4)C18—C17—H17B108.9
C3—C4—H4B109.0C16—C17—H17B108.9
C5—C4—H4B109.0H17A—C17—H17B107.7
C3—C4—H4A109.0C19—C18—C23114.1 (7)
C5—C4—H4A109.0C19—C18—C17122.4 (7)
H4B—C4—H4A107.8C23—C18—C17123.2 (5)
C10—C5—C6119.0 (5)C18—C19—C20124.2 (7)
C10—C5—C4120.3 (4)C18—C19—H19117.9
C6—C5—C4120.6 (4)C20—C19—H19117.9
C5—C6—C7119.4 (5)C21—C20—C19119.1 (6)
C5—C6—H6120.3C21—C20—H20120.4
C7—C6—H6120.3C19—C20—H20120.4
C8—C7—C6120.5 (5)C20—C21—C22120.2 (7)
C8—C7—H7119.7C20—C21—H21119.9
C6—C7—H7119.7C22—C21—H21119.9
C9—C8—C7119.7 (5)C23—C22—C21119.0 (7)
C9—C8—H8120.2C23—C22—H22120.5
C7—C8—H8120.2C21—C22—H22120.5
C8—C9—C10120.0 (5)C22—C23—C18123.2 (6)
C8—C9—H9120.0C22—C23—H23118.4
C10—C9—H9120.0C18—C23—H23118.4
C5—C10—C9121.3 (4)O6—C24—N2123.0 (4)
C5—C10—H10119.3O6—C24—C25118.7 (4)
C9—C10—H10119.3N2—C24—C25118.3 (4)
O3—C11—N1123.3 (4)C26—C25—C24133.0 (4)
O3—C11—C12120.7 (4)C26—C25—S2111.7 (3)
N1—C11—C12115.9 (4)C24—C25—S2115.4 (3)
C13—C12—C11130.6 (4)C25—C26—C26ii112.3 (3)
C13—C12—S1112.0 (3)C25—C26—H26123.8
C11—C12—S1117.2 (3)C26ii—C26—H26123.8
C12—C13—C13i112.9 (3)C11—N1—C3123.2 (4)
C12—C13—H13123.6C11—N1—H1118.4
C13i—C13—H13123.6C3—N1—H1118.4
O4A—C14A—H14B109.5C24—N2—C16122.1 (4)
O4A—C14A—H14C109.5C24—N2—H2119.0
H14B—C14A—H14C109.5C16—N2—H2119.0
O4A—C14A—H14A109.5C2—O1—C1116.6 (4)
H14B—C14A—H14A109.5C14A—O4A—C15133.5 (17)
H14C—C14A—H14A109.5C15—O4B—C14B111.0 (12)
O5A—C15—O5B116 (2)C12i—S1—C1290.3 (3)
O5B—C15—O4B131.1 (11)C25ii—S2—C2592.1 (3)
O2—C2—C3—N1169.7 (4)C17—C18—C19—C20173.7 (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—C4116.1 (4)C20—C21—C22—C234.4 (9)
N1—C3—C4—C5−71.2 (4)C21—C22—C23—C18−4.6 (10)
C2—C3—C4—C5162.7 (4)C19—C18—C23—C222.4 (9)
C3—C4—C5—C10−90.3 (5)C17—C18—C23—C22−171.2 (6)
C3—C4—C5—C685.1 (6)O6—C24—C25—C26−177.5 (5)
C10—C5—C6—C7−1.7 (9)N2—C24—C25—C261.8 (8)
C4—C5—C6—C7−177.2 (6)O6—C24—C25—S23.2 (6)
C5—C6—C7—C82.2 (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—C102.2 (10)S2—C25—C26—C26ii0.4 (8)
C6—C5—C10—C91.5 (8)O3—C11—N1—C3−13.2 (7)
C4—C5—C10—C9177.0 (5)C12—C11—N1—C3167.1 (4)
C8—C9—C10—C5−1.8 (9)C2—C3—N1—C11−95.6 (5)
O3—C11—C12—C13168.5 (5)C4—C3—N1—C11139.6 (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—C16176.3 (5)
N1—C11—C12—S1174.2 (3)C15—C16—N2—C24−99.5 (6)
C11—C12—C13—C13i−175.3 (5)C17—C16—N2—C24130.5 (6)
S1—C12—C13—C13i−1.0 (8)O2—C2—O1—C1−3.0 (8)
O5A—C15—C16—N218 (3)C3—C2—O1—C1176.1 (5)
O5B—C15—C16—N2−153.2 (7)O5A—C15—O4A—C14A−6(3)
O4B—C15—C16—N230.1 (11)O5B—C15—O4A—C14A122 (3)
O4A—C15—C16—N2171.0 (12)O4B—C15—O4A—C14A−22 (3)
O5A—C15—C16—C17145 (3)C16—C15—O4A—C14A−164.4 (18)
O5B—C15—C16—C17−25.7 (9)O5A—C15—O4B—C14B−41 (11)
O4B—C15—C16—C17157.6 (10)O5B—C15—O4B—C14B−3(2)
O4A—C15—C16—C17−61.5 (14)O4A—C15—O4B—C14B22.3 (18)
C15—C16—C17—C18161.2 (5)C16—C15—O4B—C14B173.4 (12)
N2—C16—C17—C18−71.2 (7)C13—C12—S1—C12i0.4 (3)
C16—C17—C18—C19−96.0 (7)C11—C12—S1—C12i175.5 (5)
C16—C17—C18—C2377.1 (8)C26—C25—S2—C25ii−0.1 (3)
C23—C18—C19—C200.0 (9)C24—C25—S2—C25ii179.3 (5)

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

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···O60.862.012.853 (5)164.
N2—H2···O3iii0.862.102.803 (5)139.

Symmetry codes: (iii) x, y, z−1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5003).

References

  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Oxford Diffraction (2009). CrysAlis PRO CCD and CrysAlis PRO RED Oxford Diffraction Ltd, Yarnton, England.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Xia, G.-M., Ji, M.-W., Lu, P., Sun, G.-X. & Xu, W.-F. (2010). Acta Cryst. E66, o148. [PMC free article] [PubMed]

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