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Acta Crystallogr Sect E Struct Rep Online. 2008 December 1; 64(Pt 12): o2410.
Published online 2008 November 22. doi:  10.1107/S1600536808037665
PMCID: PMC2959973

5-tert-Butyl-2-[5-(5-tert-butyl-1,3-benzoxazol-2-yl)-2-thien­yl]-1,3-benzoxazole

Abstract

The title compound, C26H26N2O2S, was prepared by the reaction of thio­phene-2,5-dicarboxylic acid and 2-amino-4-tert-butyl­phenol. One of the tert-butyl groups is disordered over two conformations, with occupancies of 0.539 (1) and 0.461 (2). The two 1,3-benzoxazole rings are almost planar, with dihedral angles of 0.83 (18) and 1.64 (17)° between the five- and six-membered rings. The thio­phene ring makes dihedral angles of 21.54 (19) and 4.49 (18)° with the planes of the five-membered oxazole rings. The crystal packing is controlled by π–π stacking inter­actions involving the thio­phene and benzene rings, with a centroid–centroid distance of 3.748 (2) Å.

Related literature

For background on fluorescent whitening agents, see: Chen et al. (2008 [triangle]). For a related structure, see: Cowley et al. (2002 [triangle]).

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Object name is e-64-o2410-scheme1.jpg

Experimental

Crystal data

  • C26H26N2O2S
  • M r = 430.56
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2410-efi1.jpg
  • a = 6.0852 (12) Å
  • b = 11.520 (2) Å
  • c = 16.986 (3) Å
  • α = 72.79 (3)°
  • β = 88.88 (3)°
  • γ = 79.32 (3)°
  • V = 1116.9 (4) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.17 mm−1
  • T = 293 (2) K
  • 0.25 × 0.20 × 0.18 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: none
  • 6826 measured reflections
  • 4783 independent reflections
  • 2940 reflections with I > 2σ(I)
  • R int = 0.031

Refinement

  • R[F 2 > 2σ(F 2)] = 0.061
  • wR(F 2) = 0.187
  • S = 1.04
  • 4783 reflections
  • 309 parameters
  • 57 restraints
  • H-atom parameters constrained
  • Δρmax = 0.48 e Å−3
  • Δρmin = −0.32 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1997 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808037665/at2649sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808037665/at2649Isup2.hkl

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

supplementary crystallographic information

Comment

Fluorescent whitening agents have received considerable attention in the literature. They are attractive from several points of view in application (Chen et al., 2008). As part of our search for new fluorescent whitening agent compounds we synthesized the title compound (I), and describe its structure here.

In (I) (Fig. 1), the C12—S1 bond length of 1.715 (3)Å is comparable with C—S bond [1.688 (2) Å] reported (Cowley et al., 2002). The two 1,3-benzoxazole rings (N1/O1/C5-C11) and (N2/O2/C16-C22) are almost planar, with dihedral angles of 0.83 (18)° and 1.64 (17)°, respectively, between the five- and six-membered rings. The thiophene ring (S1/C12-C15) makes dihedral angles of 21.54 (19)° and 4.49 (18)°, respectively, with the five membered rings (O1/N1/C7/C8/C11) and (O2/N2/C16-C18).

In the crystal structure, there is no classical hydrogen bonds. The crystal packing is controlled by π-π stacking interactions involving the thiophene (Cg1: S1/C12-C15) and benzene (Cg2i: C17-C22) [ (i) 2 - x, 1 - y, - z] rings, with a centroid-centroid distance of 3.748 (2)Å.

Experimental

A mixture of the thiophene-2,5-dicarboxylic acid (0.05 mol), and 4-tert-butyl-2-aminophenol (0.1 mol) was stirred in refluxing toluene (20 mL) for 4 h to afford the title compound (0.086 mol, yield 86%). Single crystals suitable for X-ray measurements were obtained by recrystallization from ethanol at room temperature.

Refinement

H atoms were fixed geometrically and allowed to ride on their attached atoms, with C—H distances = 0.93 and- 0.96 Å, and with Uiso=1.2 or 1.5Ueq.

Figures

Fig. 1.
The structure of the title compound showing 30% probability displacement ellipsoids and the atom-numbering scheme.

Crystal data

C26H26N2O2SZ = 2
Mr = 430.56F000 = 456
Triclinic, P1Dx = 1.280 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 6.0852 (12) ÅCell parameters from 1520 reflections
b = 11.520 (2) Åθ = 2.5–23.6º
c = 16.986 (3) ŵ = 0.17 mm1
α = 72.79 (3)ºT = 293 (2) K
β = 88.88 (3)ºBlock, yellow
γ = 79.32 (3)º0.25 × 0.20 × 0.18 mm
V = 1116.9 (4) Å3

Data collection

Bruker SMART CCD area-detector diffractometer2940 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.031
Monochromator: graphiteθmax = 27.0º
T = 293(2) Kθmin = 1.9º
[var phi] and ω scansh = −7→7
Absorption correction: nonek = −14→14
6826 measured reflectionsl = −21→17
4783 independent 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)] = 0.061H-atom parameters constrained
wR(F2) = 0.187  w = 1/[σ2(Fo2) + (0.083P)2 + 0.378P] where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
4783 reflectionsΔρmax = 0.48 e Å3
309 parametersΔρmin = −0.32 e Å3
57 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.026 (4)

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)
S10.58719 (14)0.77701 (8)0.00117 (5)0.0601 (3)
O10.2519 (4)1.00117 (19)−0.08466 (12)0.0567 (7)
O21.1731 (3)0.55542 (18)0.07064 (12)0.0517 (7)
N10.3847 (5)1.0267 (3)−0.21200 (16)0.0621 (9)
N20.8447 (4)0.5523 (2)0.13353 (16)0.0568 (9)
C1−0.1548 (7)1.4283 (4)−0.4007 (3)0.0955 (17)
C2−0.3823 (7)1.2682 (4)−0.3939 (2)0.0812 (14)
C3−0.4984 (8)1.4230 (4)−0.3198 (3)0.0971 (17)
C4−0.2957 (6)1.3431 (3)−0.34509 (19)0.0553 (10)
C5−0.1536 (5)1.2540 (3)−0.27123 (18)0.0509 (10)
C60.0494 (5)1.1872 (3)−0.28414 (18)0.0563 (10)
C70.1771 (5)1.1053 (3)−0.21673 (18)0.0513 (10)
C80.0973 (5)1.0894 (3)−0.13912 (17)0.0502 (10)
C9−0.1032 (6)1.1522 (3)−0.1232 (2)0.0639 (11)
C10−0.2260 (6)1.2345 (3)−0.19051 (19)0.0589 (11)
C110.4174 (5)0.9704 (3)−0.13440 (18)0.0522 (10)
C120.6087 (5)0.8788 (3)−0.09425 (18)0.0520 (10)
C130.8153 (6)0.8580 (3)−0.12375 (19)0.0567 (11)
C140.9600 (6)0.7598 (3)−0.06945 (19)0.0549 (11)
C150.8597 (5)0.7069 (3)0.00045 (18)0.0506 (10)
C160.9503 (5)0.6044 (3)0.07071 (19)0.0501 (10)
C171.2069 (5)0.4605 (3)0.14351 (17)0.0472 (9)
C181.0079 (5)0.4580 (3)0.18216 (18)0.0482 (10)
C190.9930 (5)0.3697 (3)0.25628 (18)0.0545 (10)
C201.1818 (5)0.2826 (3)0.29081 (18)0.0506 (10)
C211.3811 (5)0.2891 (3)0.24862 (19)0.0562 (11)
C221.4005 (5)0.3778 (3)0.17496 (19)0.0543 (10)
C231.1718 (5)0.1827 (3)0.37112 (19)0.0642 (11)
C241.3987 (10)0.1150 (10)0.4102 (6)0.163 (4)0.539 (8)
C251.0524 (16)0.0853 (6)0.3523 (4)0.098 (3)0.539 (8)
C261.0314 (17)0.2331 (7)0.4322 (4)0.112 (4)0.539 (8)
C26'0.9370 (10)0.1644 (12)0.3948 (8)0.160 (5)0.461 (8)
C24'1.273 (2)0.2224 (8)0.4398 (5)0.104 (4)0.461 (8)
C25'1.3145 (18)0.0592 (6)0.3717 (6)0.111 (4)0.461 (8)
H1A−0.245701.48400−0.446900.1440*
H1B−0.032501.37960−0.420200.1440*
H1C−0.097201.47480−0.370200.1440*
H2A−0.472201.32330−0.440600.1220*
H3B−0.448201.47120−0.288700.1450*
H3C−0.592001.37060−0.286400.1450*
H6A0.100101.19690−0.337300.0680*
H9A−0.154001.14010−0.069900.0760*
H2B−0.471201.21410−0.359300.1220*
H2C−0.258001.21990−0.412600.1220*
H3A−0.582001.47730−0.368200.1450*
H19A0.857900.368500.282800.0650*
H21A1.507600.230400.271500.0680*
H22A1.535300.381400.148500.0650*
H24A1.448400.045300.390100.2450*0.539 (8)
H24B1.387800.086900.469000.2450*0.539 (8)
H24C1.503900.170000.396300.2450*0.539 (8)
H25A0.996700.114800.296000.1460*0.539 (8)
H25B0.930100.072200.388300.1460*0.539 (8)
H25C1.156800.008800.360800.1460*0.539 (8)
H26A0.875800.239000.419700.1680*0.539 (8)
H26B1.059600.313700.428800.1680*0.539 (8)
H26C1.069400.178700.487000.1680*0.539 (8)
H10A−0.363301.27920−0.181900.0710*
H13A0.856800.90420−0.174700.0680*
H14A1.108500.73370−0.080100.0660*
H24D1.337800.294100.415400.1560*0.461 (8)
H24E1.387100.156000.470900.1560*0.461 (8)
H24F1.157800.241400.475800.1560*0.461 (8)
H25D1.245300.024600.335900.1670*0.461 (8)
H25E1.327700.003600.426800.1670*0.461 (8)
H25F1.460600.071500.352800.1670*0.461 (8)
H26D0.863500.148700.350500.2400*0.461 (8)
H26E0.854900.237500.405300.2400*0.461 (8)
H26F0.943600.095200.443500.2400*0.461 (8)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0560 (5)0.0611 (5)0.0504 (5)−0.0031 (4)−0.0010 (4)−0.0020 (4)
O20.0479 (12)0.0515 (11)0.0502 (12)−0.0087 (9)−0.0014 (9)−0.0071 (9)
O10.0662 (14)0.0563 (12)0.0404 (11)−0.0022 (11)−0.0055 (10)−0.0086 (9)
N10.0601 (17)0.0672 (17)0.0474 (15)0.0009 (14)−0.0021 (12)−0.0072 (13)
N20.0476 (15)0.0606 (15)0.0517 (15)−0.0058 (12)−0.0029 (12)−0.0030 (12)
C10.096 (3)0.072 (3)0.093 (3)−0.018 (2)−0.024 (2)0.017 (2)
C20.091 (3)0.079 (2)0.073 (2)−0.004 (2)−0.028 (2)−0.027 (2)
C30.101 (3)0.095 (3)0.081 (3)0.036 (3)−0.025 (2)−0.036 (2)
C40.062 (2)0.0510 (17)0.0498 (17)−0.0043 (15)−0.0088 (15)−0.0136 (14)
C50.060 (2)0.0474 (16)0.0457 (17)−0.0102 (14)−0.0036 (14)−0.0142 (13)
C60.063 (2)0.0590 (18)0.0402 (16)−0.0035 (16)0.0005 (14)−0.0094 (13)
C70.0578 (19)0.0460 (16)0.0454 (17)−0.0063 (14)0.0001 (14)−0.0087 (13)
C80.063 (2)0.0462 (16)0.0393 (16)−0.0076 (14)−0.0022 (14)−0.0107 (12)
C90.073 (2)0.071 (2)0.0438 (17)−0.0045 (18)0.0058 (16)−0.0170 (15)
C100.061 (2)0.0587 (19)0.0548 (19)−0.0007 (16)−0.0010 (15)−0.0200 (15)
C110.0556 (19)0.0516 (17)0.0470 (17)−0.0095 (14)−0.0017 (14)−0.0110 (14)
C120.058 (2)0.0505 (17)0.0451 (16)−0.0104 (14)−0.0066 (14)−0.0098 (13)
C130.062 (2)0.0580 (18)0.0468 (17)−0.0165 (16)−0.0009 (15)−0.0071 (14)
C140.0524 (19)0.0587 (18)0.0517 (18)−0.0119 (15)0.0000 (14)−0.0126 (14)
C150.0501 (18)0.0497 (16)0.0481 (17)−0.0081 (14)−0.0054 (14)−0.0089 (13)
C160.0460 (17)0.0499 (16)0.0522 (18)−0.0063 (14)−0.0045 (14)−0.0130 (14)
C170.0506 (18)0.0442 (15)0.0450 (16)−0.0111 (13)−0.0034 (13)−0.0089 (12)
C180.0430 (17)0.0492 (16)0.0488 (17)−0.0039 (13)−0.0017 (13)−0.0117 (13)
C190.0480 (18)0.0606 (18)0.0500 (17)−0.0110 (15)0.0031 (14)−0.0086 (14)
C200.0497 (18)0.0504 (16)0.0494 (17)−0.0081 (14)−0.0056 (14)−0.0119 (13)
C210.0496 (18)0.0532 (18)0.0602 (19)−0.0018 (14)−0.0120 (15)−0.0121 (15)
C220.0417 (17)0.0567 (18)0.0612 (19)−0.0060 (14)0.0003 (14)−0.0143 (15)
C230.063 (2)0.062 (2)0.0541 (19)−0.0060 (17)−0.0094 (16)0.0005 (15)
C240.120 (7)0.187 (9)0.111 (7)−0.025 (7)−0.024 (6)0.062 (6)
C250.149 (8)0.065 (4)0.072 (5)−0.040 (5)0.013 (5)0.002 (3)
C260.182 (9)0.084 (5)0.059 (4)−0.017 (6)0.040 (5)−0.013 (4)
C24'0.168 (9)0.087 (6)0.051 (4)−0.022 (6)−0.015 (5)−0.010 (4)
C25'0.178 (10)0.046 (4)0.091 (6)0.001 (5)0.022 (6)−0.007 (4)
C26'0.105 (7)0.175 (10)0.143 (9)−0.048 (7)0.010 (7)0.053 (7)

Geometric parameters (Å, °)

S1—C151.706 (3)C14—H14A0.9300
S1—C121.715 (3)C15—C161.440 (4)
O2—C161.369 (3)C17—C181.367 (4)
O2—C171.377 (3)C17—C221.374 (4)
O1—C111.366 (4)C18—C191.379 (4)
O1—C81.377 (3)C19—C201.386 (4)
N1—C111.286 (4)C19—H19A0.9300
N1—C71.400 (4)C20—C211.399 (4)
N2—C161.284 (4)C20—C231.511 (4)
N2—C181.397 (4)C21—C221.380 (4)
C1—C41.524 (5)C21—H21A0.9300
C1—H1A0.9600C22—H22A0.9300
C1—H1B0.9600C23—C261.511 (4)
C1—H1C0.9600C23—C26'1.512 (5)
C2—C41.523 (5)C23—C241.512 (5)
C2—H2A0.9600C23—C25'1.521 (5)
C2—H2B0.9600C23—C24'1.550 (5)
C2—H2C0.9600C23—C251.553 (4)
C3—C41.531 (5)C24—H24A0.9600
C3—H3A0.9600C24—H24B0.9600
C3—H3B0.9600C24—H24C0.9600
C3—H3C0.9600C25—H25A0.9600
C4—C51.526 (4)C25—H25B0.9600
C5—C61.379 (4)C25—H25C0.9600
C5—C101.398 (4)C26—H26A0.9600
C6—C71.389 (4)C26—H26B0.9600
C6—H6A0.9300C26—H26C0.9600
C7—C81.368 (4)C24'—H24D0.9600
C8—C91.365 (5)C24'—H24E0.9600
C9—C101.376 (4)C24'—H24F0.9600
C9—H9A0.9300C25'—H25D0.9600
C10—H10A0.9300C25'—H25E0.9600
C11—C121.444 (4)C25'—H25F0.9600
C12—C131.350 (4)C26'—H26D0.9600
C13—C141.397 (4)C26'—H26E0.9600
C13—H13A0.9300C26'—H26F0.9600
C14—C151.355 (4)
C15—S1—C1290.76 (15)C19—C18—N2130.7 (3)
C16—O2—C17103.0 (2)C18—C19—C20119.2 (3)
C11—O1—C8103.4 (2)C18—C19—H19A120.4
C11—N1—C7103.6 (3)C20—C19—H19A120.4
C16—N2—C18104.0 (3)C19—C20—C21118.0 (3)
C4—C1—H1A109.5C19—C20—C23120.9 (3)
C4—C1—H1B109.5C21—C20—C23121.1 (3)
H1A—C1—H1B109.5C22—C21—C20123.7 (3)
C4—C1—H1C109.5C22—C21—H21A118.1
H1A—C1—H1C109.5C20—C21—H21A118.1
H1B—C1—H1C109.5C17—C22—C21115.4 (3)
C4—C2—H2A109.5C17—C22—H22A122.3
C4—C2—H2B109.5C21—C22—H22A122.3
H2A—C2—H2B109.5C26—C23—C20111.4 (4)
C4—C2—H2C109.5C26—C23—C26'53.4 (5)
H2A—C2—H2C109.5C20—C23—C26'113.9 (5)
H2B—C2—H2C109.5C26—C23—C24110.0 (3)
C4—C3—H3A109.5C20—C23—C24114.0 (5)
C4—C3—H3B109.5C26'—C23—C24132.0 (6)
H3A—C3—H3B109.5C26—C23—C25'136.2 (5)
C4—C3—H3C109.5C20—C23—C25'112.4 (4)
H3A—C3—H3C109.5C26'—C23—C25'109.2 (4)
H3B—C3—H3C109.5C24—C23—C25'47.4 (4)
C2—C4—C1108.9 (3)C26—C23—C24'56.9 (4)
C2—C4—C5108.7 (3)C20—C23—C24'107.2 (4)
C1—C4—C5110.1 (3)C26'—C23—C24'107.4 (4)
C2—C4—C3107.8 (3)C24—C23—C24'60.3 (4)
C1—C4—C3108.6 (3)C25'—C23—C24'106.3 (4)
C5—C4—C3112.7 (3)C26—C23—C25106.7 (3)
C6—C5—C10118.6 (3)C20—C23—C25107.4 (3)
C6—C5—C4119.4 (3)C26'—C23—C2554.6 (5)
C10—C5—C4122.0 (3)C24—C23—C25107.0 (3)
C5—C6—C7119.1 (3)C25'—C23—C2562.3 (4)
C5—C6—H6A120.4C24'—C23—C25145.2 (5)
C7—C6—H6A120.4C23—C24—H24A109.5
C8—C7—C6119.8 (3)C23—C24—H24B109.5
C8—C7—N1109.2 (3)H24A—C24—H24B109.5
C6—C7—N1131.1 (3)C23—C24—H24C109.5
C9—C8—C7123.4 (3)H24A—C24—H24C109.5
C9—C8—O1128.8 (3)H24B—C24—H24C109.5
C7—C8—O1107.9 (3)C23—C25—H25A109.5
C8—C9—C10116.1 (3)C23—C25—H25B109.5
C8—C9—H9A121.9H25A—C25—H25B109.5
C10—C9—H9A121.9C23—C25—H25C109.5
C9—C10—C5123.0 (3)H25A—C25—H25C109.5
C9—C10—H10A118.5H25B—C25—H25C109.5
C5—C10—H10A118.5C23—C26—H26A109.5
N1—C11—O1116.0 (3)C23—C26—H26B109.5
N1—C11—C12127.4 (3)H26A—C26—H26B109.5
O1—C11—C12116.6 (3)C23—C26—H26C109.5
C13—C12—C11127.6 (3)H26A—C26—H26C109.5
C13—C12—S1111.9 (2)H26B—C26—H26C109.5
C11—C12—S1120.4 (3)C23—C24'—H24D109.5
C12—C13—C14112.7 (3)C23—C24'—H24E109.5
C12—C13—H13A123.6H24D—C24'—H24E109.5
C14—C13—H13A123.6C23—C24'—H24F109.5
C15—C14—C13112.4 (3)H24D—C24'—H24F109.5
C15—C14—H14A123.8H24E—C24'—H24F109.5
C13—C14—H14A123.8C23—C25'—H25D109.5
C14—C15—C16129.5 (3)C23—C25'—H25E109.5
C14—C15—S1112.2 (2)H25D—C25'—H25E109.5
C16—C15—S1118.3 (2)C23—C25'—H25F109.5
N2—C16—O2115.9 (3)H25D—C25'—H25F109.5
N2—C16—C15127.2 (3)H25E—C25'—H25F109.5
O2—C16—C15116.9 (3)C23—C26'—H26D109.5
C18—C17—C22123.2 (3)C23—C26'—H26E109.5
C18—C17—O2108.3 (2)H26D—C26'—H26E109.5
C22—C17—O2128.5 (3)C23—C26'—H26F109.5
C17—C18—C19120.5 (3)H26D—C26'—H26F109.5
C17—C18—N2108.8 (3)H26E—C26'—H26F109.5
C2—C4—C5—C668.7 (4)C12—S1—C15—C16179.9 (2)
C1—C4—C5—C6−50.5 (4)C18—N2—C16—O2−0.1 (4)
C3—C4—C5—C6−171.8 (3)C18—N2—C16—C15179.1 (3)
C2—C4—C5—C10−109.1 (4)C17—O2—C16—N20.1 (3)
C1—C4—C5—C10131.7 (4)C17—O2—C16—C15−179.2 (2)
C3—C4—C5—C1010.4 (5)C14—C15—C16—N2−175.3 (3)
C10—C5—C6—C7−1.5 (5)S1—C15—C16—N25.0 (4)
C4—C5—C6—C7−179.4 (3)C14—C15—C16—O23.9 (5)
C5—C6—C7—C81.9 (5)S1—C15—C16—O2−175.8 (2)
C5—C6—C7—N1179.6 (3)C16—O2—C17—C180.0 (3)
C11—N1—C7—C8−0.3 (4)C16—O2—C17—C22178.8 (3)
C11—N1—C7—C6−178.1 (3)C22—C17—C18—C19−0.2 (5)
C6—C7—C8—C9−1.2 (5)O2—C17—C18—C19178.7 (3)
N1—C7—C8—C9−179.4 (3)C22—C17—C18—N2−178.9 (3)
C6—C7—C8—O1178.0 (3)O2—C17—C18—N20.0 (3)
N1—C7—C8—O1−0.1 (3)C16—N2—C18—C170.0 (3)
C11—O1—C8—C9179.6 (3)C16—N2—C18—C19−178.5 (3)
C11—O1—C8—C70.4 (3)C17—C18—C19—C20−0.6 (5)
C7—C8—C9—C100.2 (5)N2—C18—C19—C20177.8 (3)
O1—C8—C9—C10−179.0 (3)C18—C19—C20—C210.4 (4)
C8—C9—C10—C50.2 (5)C18—C19—C20—C23−178.8 (3)
C6—C5—C10—C90.4 (5)C19—C20—C21—C220.5 (5)
C4—C5—C10—C9178.3 (3)C23—C20—C21—C22179.8 (3)
C7—N1—C11—O10.6 (4)C18—C17—C22—C211.0 (4)
C7—N1—C11—C12−179.3 (3)O2—C17—C22—C21−177.6 (3)
C8—O1—C11—N1−0.6 (4)C20—C21—C22—C17−1.2 (5)
C8—O1—C11—C12179.3 (3)C19—C20—C23—C26−41.2 (5)
N1—C11—C12—C1320.3 (6)C21—C20—C23—C26139.6 (5)
O1—C11—C12—C13−159.6 (3)C19—C20—C23—C26'17.0 (7)
N1—C11—C12—S1−157.8 (3)C21—C20—C23—C26'−162.3 (6)
O1—C11—C12—S122.3 (4)C19—C20—C23—C24−166.3 (5)
C15—S1—C12—C130.1 (3)C21—C20—C23—C2414.5 (6)
C15—S1—C12—C11178.5 (3)C19—C20—C23—C25'141.8 (5)
C11—C12—C13—C14−178.5 (3)C21—C20—C23—C25'−37.4 (6)
S1—C12—C13—C14−0.3 (4)C19—C20—C23—C24'−101.7 (5)
C12—C13—C14—C150.4 (4)C21—C20—C23—C24'79.0 (6)
C13—C14—C15—C16179.9 (3)C19—C20—C23—C2575.3 (5)
C13—C14—C15—S1−0.4 (4)C21—C20—C23—C25−104.0 (5)
C12—S1—C15—C140.2 (3)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2649).

References

  • Bruker (1997). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Chen, B., Wen, J. & Chen, J.-H. (2008). J. Taiyuan Univ. Technol.39, 241–244.
  • Cowley, A. R., Dilworth, J. R. & Dorinelly, P. S. (2002). J. Am. Chem. Soc.124, 5270–5271. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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