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Acta Crystallogr Sect E Struct Rep Online. 2009 August 1; 65(Pt 8): o1792.
Published online 2009 July 8. doi:  10.1107/S1600536809025070
PMCID: PMC2977147

11-(p-Tolylsulfonyl)-8,14,24-trioxa-11,22,23-triazatetracyclo[19.2.1.02,7.015,20]tetracosa-1(23),2,4,6,15,17,19,21-octaene

Abstract

In the title compound, C25H23N3O5S, the central 1,3,4-oxadiazole ring makes dihedral angles of 35.05 (7), 23.68 (7) and 82.55 (8)°, with the three benzene rings. In the crystal structure, the packing is stabilized by weak non-classical inter­molecular C—H(...)O hydrogen bonds, which link the mol­ecules into an infinite network.

Related literature

For related structures, see: Du, Hua & Jin (2001 [triangle]). For applications and synthesis of fluorescent sensors, see: Tong et al. (2000 [triangle]); Silva et al. (2000 [triangle]); Valeur & Leray (2000 [triangle]). For reference geometrical data, see: Du, Hua, Wang & Yan (2001 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1792-scheme1.jpg

Experimental

Crystal data

  • C25H23N3O5S
  • M r = 477.52
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1792-efi1.jpg
  • a = 13.0474 (19) Å
  • b = 9.6809 (14) Å
  • c = 18.261 (3) Å
  • β = 97.479 (3)°
  • V = 2286.9 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.19 mm−1
  • T = 294 K
  • 0.30 × 0.22 × 0.20 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.932, T max = 0.964
  • 12599 measured reflections
  • 4656 independent reflections
  • 2878 reflections with I > 2σ(I)
  • R int = 0.044

Refinement

  • R[F 2 > 2σ(F 2)] = 0.041
  • wR(F 2) = 0.106
  • S = 1.01
  • 4656 reflections
  • 308 parameters
  • H-atom parameters constrained
  • Δρmax = 0.20 e Å−3
  • Δρmin = −0.33 e Å−3

Data collection: SMART (Bruker, 1999 [triangle]); cell refinement: SAINT (Bruker, 1999 [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.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809025070/pv2175sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809025070/pv2175Isup2.hkl

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

Acknowledgments

This work was supported by the NSFC of Hebei Province (No. B2009000670), the Foundation of the Education Department of Hebei Province and the Foundation of Hebei University of Science & Technology (No. XL200746), which are gratefully acknowledged.

supplementary crystallographic information

Comment

The development of fluorescent sensors for organic molecules is of great practical importance in chemical, biological, and pharmaceutical sciences (Silva et al., 2000; Valeur et al., 2000). Therefore, the design and synthesis of new functionalized macrocycles for selective recognition of other species is of great interest to chemists. Many functionalized macrocycles have been synthesized and employed to develop fluorescent sensors (Tong et al., 2000). 2,5-Diaryl-1,3,4-oxadizole forms chiral macrocyclic phosphoramidate receptors with phosphorus oxychloride, and their crystal structures have been reported (Du, Hua & Jin, 2001). As part of an investigation of the potential recognition properties of macrocycles, we now reported the synthesis and structure of the title compound, (I).

The molecular structure of (I) is presented in Fig. 1. The oxadizole ring (O1/C1/N1/N2/C18) is nearly planar, with an r.m.s. deviation for fitted atoms of 0.0017 Å. It makes dihedral angles of 35.05 (7), 23.68 (7) and 82.55 (8)°, respectively, with the benzene rings (C2—C7), (C12—C17) and (C19—C24). The crystal packing is stabilized by weak non-classical intermolecular C—H···O hydrogen bonds which link the molecules into an infinite network. The bond lengths and angles in (I) are within their normal ranges (Du, Hua, Wang & Yan 2001).

Experimental

2,5-Di(o-hydroxyphenyl)-1,3,4-oxadiazole (0.8 g, 3.0 mmol), K2CO3 (1.4 g, 10 mmol) and tri-(p-phenylsulfonyl) diethanol amine (2.3 g, 4 mmol) were added and dissolved in 50 ml of DMF and the mixture was stirred at 413 K for 20 h giving a colourless precipitate. The product was isolated, recrystallized from ethyl acetate then dried in a vacuum to give the pure compound in 65% yield. colourless single crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of ethyl acetate.

Refinement

The H atoms were included in calculated positions (C—H = 0.93–0.97 Å) and refined as riding with Uiso(H) = 1.2Ueq(C)or 1.5Ueq(methyl C).

Figures

Fig. 1.
The molecular structure of (I) with displacement ellipsoids for non-H atoms drawn at the 30% probability level.
Fig. 2.
Packing diagram for (I), with H bonds drawn as dashed lines; H-atoms not involved in interactions have been excluded.

Crystal data

C25H23N3O5SF(000) = 1000
Mr = 477.52Dx = 1.387 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3043 reflections
a = 13.0474 (19) Åθ = 2.4–24.5°
b = 9.6809 (14) ŵ = 0.19 mm1
c = 18.261 (3) ÅT = 294 K
β = 97.479 (3)°Prism, colourless
V = 2286.9 (6) Å30.30 × 0.22 × 0.20 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer4656 independent reflections
Radiation source: fine-focus sealed tube2878 reflections with I > 2σ(I)
graphiteRint = 0.044
[var phi] and ω scansθmax = 26.4°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −14→16
Tmin = 0.932, Tmax = 0.964k = −12→11
12599 measured reflectionsl = −18→22

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106H-atom parameters constrained
S = 1.00w = 1/[σ2(Fo2) + (0.0446P)2 + 0.4604P] where P = (Fo2 + 2Fc2)/3
4656 reflections(Δ/σ)max = 0.001
308 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = −0.33 e Å3

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*/Ueq
S10.08777 (4)1.10726 (6)0.12913 (3)0.03359 (16)
N10.52489 (14)0.5209 (2)0.19897 (11)0.0429 (5)
N20.56917 (14)0.5766 (2)0.13898 (11)0.0433 (5)
N30.18176 (14)0.99856 (19)0.12592 (10)0.0368 (5)
O10.40350 (11)0.62864 (15)0.12555 (8)0.0346 (4)
O20.26584 (14)0.73372 (16)0.20414 (9)0.0478 (5)
O30.35451 (12)0.84722 (17)0.04510 (8)0.0452 (4)
O4−0.00564 (11)1.04490 (16)0.09383 (9)0.0417 (4)
O50.09239 (13)1.15346 (17)0.20368 (9)0.0470 (4)
C10.42829 (17)0.5545 (2)0.18849 (12)0.0317 (5)
C20.34817 (16)0.5205 (2)0.23424 (11)0.0317 (5)
C30.35206 (18)0.3940 (2)0.27068 (12)0.0397 (6)
H30.40590.33310.26580.048*
C40.27714 (19)0.3576 (2)0.31399 (13)0.0437 (6)
H40.28030.27280.33810.052*
C50.19776 (19)0.4482 (3)0.32114 (13)0.0443 (6)
H50.14670.42360.34980.053*
C60.19281 (19)0.5752 (2)0.28641 (13)0.0424 (6)
H60.13930.63600.29240.051*
C70.26729 (18)0.6122 (2)0.24268 (12)0.0354 (5)
C80.2383 (2)0.8580 (2)0.23870 (13)0.0436 (6)
H8A0.27830.86720.28710.052*
H8B0.16560.85630.24480.052*
C90.26014 (17)0.9778 (2)0.19023 (12)0.0380 (6)
H9A0.26531.06140.21970.046*
H9B0.32660.96290.17310.046*
C100.18136 (17)0.9098 (2)0.06069 (12)0.0354 (5)
H10A0.11650.92360.02910.042*
H10B0.18320.81430.07690.042*
C110.26861 (17)0.9320 (2)0.01498 (13)0.0393 (6)
H11A0.24650.9067−0.03600.047*
H11B0.28881.02850.01650.047*
C120.42882 (17)0.8148 (2)0.00178 (12)0.0351 (5)
C130.43787 (18)0.8787 (3)−0.06523 (13)0.0429 (6)
H130.39090.9467−0.08330.052*
C140.51633 (19)0.8415 (3)−0.10495 (14)0.0473 (7)
H140.52110.8837−0.15010.057*
C150.58800 (19)0.7424 (3)−0.07867 (14)0.0470 (7)
H150.64130.7190−0.10550.056*
C160.57964 (18)0.6787 (2)−0.01234 (13)0.0413 (6)
H160.62780.61190.00540.050*
C170.50033 (16)0.7125 (2)0.02867 (12)0.0323 (5)
C180.49498 (16)0.6389 (2)0.09783 (12)0.0320 (5)
C190.11113 (16)1.2493 (2)0.07299 (12)0.0329 (5)
C200.09314 (19)1.2366 (2)−0.00310 (13)0.0418 (6)
H200.06871.1537−0.02440.050*
C210.1115 (2)1.3470 (3)−0.04719 (14)0.0483 (7)
H210.09931.3378−0.09830.058*
C220.14769 (19)1.4715 (2)−0.01674 (15)0.0450 (6)
C230.16432 (19)1.4821 (2)0.05905 (15)0.0491 (7)
H230.18831.56510.08040.059*
C240.14638 (18)1.3728 (2)0.10435 (14)0.0425 (6)
H240.15801.38250.15540.051*
C250.1681 (3)1.5912 (3)−0.06588 (18)0.0734 (9)
H25A0.13361.6721−0.05110.110*
H25B0.14251.5692−0.11620.110*
H25C0.24111.6082−0.06160.110*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0316 (3)0.0310 (3)0.0389 (3)0.0016 (2)0.0070 (2)−0.0041 (3)
N10.0330 (12)0.0535 (13)0.0413 (12)0.0021 (10)0.0018 (9)0.0105 (10)
N20.0297 (11)0.0533 (13)0.0470 (12)0.0021 (9)0.0046 (9)0.0092 (11)
N30.0369 (11)0.0369 (11)0.0345 (11)0.0112 (9)−0.0032 (8)−0.0079 (9)
O10.0283 (8)0.0425 (9)0.0338 (9)0.0033 (7)0.0068 (7)0.0083 (7)
O20.0724 (12)0.0332 (9)0.0422 (10)0.0133 (8)0.0241 (9)0.0074 (8)
O30.0427 (10)0.0574 (11)0.0379 (9)0.0199 (8)0.0143 (8)0.0123 (8)
O40.0284 (8)0.0413 (9)0.0558 (10)−0.0063 (7)0.0069 (7)−0.0041 (8)
O50.0565 (11)0.0475 (10)0.0388 (10)0.0057 (8)0.0130 (8)−0.0086 (8)
C10.0338 (13)0.0307 (12)0.0296 (12)−0.0003 (10)0.0005 (10)0.0015 (10)
C20.0346 (13)0.0328 (12)0.0268 (12)−0.0005 (10)0.0011 (10)0.0009 (10)
C30.0420 (14)0.0397 (13)0.0370 (14)0.0039 (11)0.0042 (11)0.0031 (12)
C40.0531 (16)0.0376 (13)0.0414 (14)−0.0006 (12)0.0099 (12)0.0082 (12)
C50.0472 (15)0.0469 (15)0.0415 (14)−0.0025 (12)0.0163 (12)0.0051 (12)
C60.0444 (14)0.0436 (15)0.0415 (14)0.0086 (11)0.0144 (12)0.0017 (12)
C70.0447 (14)0.0359 (13)0.0261 (12)0.0028 (11)0.0065 (10)0.0017 (10)
C80.0556 (16)0.0386 (14)0.0376 (14)0.0100 (12)0.0100 (12)−0.0022 (11)
C90.0374 (13)0.0351 (13)0.0394 (14)0.0019 (10)−0.0033 (11)−0.0012 (11)
C100.0348 (13)0.0323 (12)0.0382 (13)0.0060 (10)0.0013 (10)−0.0053 (11)
C110.0410 (14)0.0378 (13)0.0382 (13)0.0092 (11)0.0019 (11)0.0056 (11)
C120.0318 (13)0.0421 (14)0.0323 (13)0.0005 (11)0.0079 (10)−0.0021 (11)
C130.0377 (14)0.0531 (16)0.0382 (14)0.0018 (12)0.0060 (11)0.0086 (12)
C140.0455 (16)0.0631 (17)0.0344 (14)−0.0098 (13)0.0097 (12)0.0043 (13)
C150.0371 (14)0.0630 (17)0.0436 (15)−0.0064 (13)0.0159 (12)−0.0067 (14)
C160.0343 (14)0.0472 (15)0.0436 (15)0.0004 (11)0.0098 (11)−0.0036 (12)
C170.0282 (12)0.0350 (12)0.0339 (13)−0.0025 (10)0.0054 (10)−0.0024 (10)
C180.0254 (12)0.0338 (12)0.0370 (13)−0.0006 (10)0.0044 (10)−0.0028 (10)
C190.0266 (12)0.0301 (12)0.0415 (14)0.0044 (9)0.0022 (10)−0.0040 (11)
C200.0510 (15)0.0307 (13)0.0437 (15)−0.0045 (11)0.0056 (12)−0.0087 (12)
C210.0591 (17)0.0454 (15)0.0414 (15)−0.0025 (13)0.0096 (13)−0.0019 (13)
C220.0445 (15)0.0355 (14)0.0558 (17)0.0005 (11)0.0093 (12)0.0040 (13)
C230.0549 (17)0.0289 (13)0.0609 (18)−0.0068 (12)−0.0022 (13)−0.0063 (13)
C240.0474 (15)0.0337 (14)0.0441 (15)−0.0008 (11)−0.0022 (12)−0.0059 (12)
C250.094 (2)0.0480 (17)0.080 (2)−0.0076 (16)0.0186 (19)0.0143 (16)

Geometric parameters (Å, °)

S1—O51.4268 (16)C10—C111.512 (3)
S1—O41.4355 (16)C10—H10A0.9700
S1—N31.6227 (18)C10—H10B0.9700
S1—C191.765 (2)C11—H11A0.9700
N1—C11.292 (3)C11—H11B0.9700
N1—N21.410 (2)C12—C131.390 (3)
N2—C181.295 (3)C12—C171.405 (3)
N3—C91.467 (3)C13—C141.377 (3)
N3—C101.468 (3)C13—H130.9300
O1—C11.358 (2)C14—C151.381 (3)
O1—C181.359 (2)C14—H140.9300
O2—C71.370 (3)C15—C161.376 (3)
O2—C81.426 (3)C15—H150.9300
O3—C121.365 (2)C16—C171.393 (3)
O3—C111.439 (3)C16—H160.9300
C1—C21.458 (3)C17—C181.459 (3)
C2—C31.392 (3)C19—C241.379 (3)
C2—C71.403 (3)C19—C201.384 (3)
C3—C41.381 (3)C20—C211.378 (3)
C3—H30.9300C20—H200.9300
C4—C51.376 (3)C21—C221.384 (3)
C4—H40.9300C21—H210.9300
C5—C61.381 (3)C22—C231.377 (3)
C5—H50.9300C22—C251.510 (3)
C6—C71.383 (3)C23—C241.381 (3)
C6—H60.9300C23—H230.9300
C8—C91.508 (3)C24—H240.9300
C8—H8A0.9700C25—H25A0.9600
C8—H8B0.9700C25—H25B0.9600
C9—H9A0.9700C25—H25C0.9600
C9—H9B0.9700
O5—S1—O4119.22 (10)H10A—C10—H10B107.4
O5—S1—N3107.43 (10)O3—C11—C10108.23 (17)
O4—S1—N3108.21 (9)O3—C11—H11A110.1
O5—S1—C19108.71 (10)C10—C11—H11A110.1
O4—S1—C19105.52 (10)O3—C11—H11B110.1
N3—S1—C19107.21 (10)C10—C11—H11B110.1
C1—N1—N2106.20 (18)H11A—C11—H11B108.4
C18—N2—N1106.15 (17)O3—C12—C13123.8 (2)
C9—N3—C10119.84 (17)O3—C12—C17116.69 (19)
C9—N3—S1120.75 (15)C13—C12—C17119.5 (2)
C10—N3—S1119.07 (14)C14—C13—C12120.1 (2)
C1—O1—C18103.30 (16)C14—C13—H13120.0
C7—O2—C8118.99 (17)C12—C13—H13120.0
C12—O3—C11119.08 (17)C13—C14—C15121.0 (2)
N1—C1—O1112.27 (18)C13—C14—H14119.5
N1—C1—C2128.1 (2)C15—C14—H14119.5
O1—C1—C2119.65 (18)C16—C15—C14119.3 (2)
C3—C2—C7119.0 (2)C16—C15—H15120.3
C3—C2—C1119.2 (2)C14—C15—H15120.3
C7—C2—C1121.7 (2)C15—C16—C17121.2 (2)
C4—C3—C2120.9 (2)C15—C16—H16119.4
C4—C3—H3119.5C17—C16—H16119.4
C2—C3—H3119.5C16—C17—C12118.9 (2)
C5—C4—C3119.3 (2)C16—C17—C18118.3 (2)
C5—C4—H4120.4C12—C17—C18122.82 (19)
C3—C4—H4120.4N2—C18—O1112.08 (19)
C4—C5—C6121.0 (2)N2—C18—C17127.8 (2)
C4—C5—H5119.5O1—C18—C17120.08 (19)
C6—C5—H5119.5C24—C19—C20119.8 (2)
C5—C6—C7120.1 (2)C24—C19—S1120.53 (18)
C5—C6—H6120.0C20—C19—S1119.62 (17)
C7—C6—H6120.0C21—C20—C19119.9 (2)
O2—C7—C6123.7 (2)C21—C20—H20120.1
O2—C7—C2116.57 (19)C19—C20—H20120.1
C6—C7—C2119.7 (2)C20—C21—C22121.1 (2)
O2—C8—C9108.12 (18)C20—C21—H21119.4
O2—C8—H8A110.1C22—C21—H21119.4
C9—C8—H8A110.1C23—C22—C21118.0 (2)
O2—C8—H8B110.1C23—C22—C25121.6 (2)
C9—C8—H8B110.1C21—C22—C25120.4 (2)
H8A—C8—H8B108.4C22—C23—C24121.9 (2)
N3—C9—C8114.2 (2)C22—C23—H23119.1
N3—C9—H9A108.7C24—C23—H23119.1
C8—C9—H9A108.7C19—C24—C23119.3 (2)
N3—C9—H9B108.7C19—C24—H24120.4
C8—C9—H9B108.7C23—C24—H24120.4
H9A—C9—H9B107.6C22—C25—H25A109.5
N3—C10—C11116.19 (19)C22—C25—H25B109.5
N3—C10—H10A108.2H25A—C25—H25B109.5
C11—C10—H10A108.2C22—C25—H25C109.5
N3—C10—H10B108.2H25A—C25—H25C109.5
C11—C10—H10B108.2H25B—C25—H25C109.5
C1—N1—N2—C180.1 (2)C11—O3—C12—C17−168.81 (19)
O5—S1—N3—C9−7.8 (2)O3—C12—C13—C14178.8 (2)
O4—S1—N3—C9−137.76 (17)C17—C12—C13—C140.2 (3)
C19—S1—N3—C9108.86 (18)C12—C13—C14—C15−1.1 (4)
O5—S1—N3—C10165.50 (16)C13—C14—C15—C161.0 (4)
O4—S1—N3—C1035.56 (19)C14—C15—C16—C17−0.1 (4)
C19—S1—N3—C10−77.82 (18)C15—C16—C17—C12−0.8 (3)
N2—N1—C1—O10.2 (2)C15—C16—C17—C18178.9 (2)
N2—N1—C1—C2179.1 (2)O3—C12—C17—C16−178.0 (2)
C18—O1—C1—N1−0.4 (2)C13—C12—C17—C160.8 (3)
C18—O1—C1—C2−179.42 (19)O3—C12—C17—C182.3 (3)
N1—C1—C2—C3−34.2 (3)C13—C12—C17—C18−178.9 (2)
O1—C1—C2—C3144.6 (2)N1—N2—C18—O1−0.4 (2)
N1—C1—C2—C7145.6 (2)N1—N2—C18—C17−179.5 (2)
O1—C1—C2—C7−35.6 (3)C1—O1—C18—N20.5 (2)
C7—C2—C3—C40.7 (3)C1—O1—C18—C17179.69 (19)
C1—C2—C3—C4−179.5 (2)C16—C17—C18—N223.2 (3)
C2—C3—C4—C5−0.1 (4)C12—C17—C18—N2−157.1 (2)
C3—C4—C5—C6−0.8 (4)C16—C17—C18—O1−155.8 (2)
C4—C5—C6—C71.1 (4)C12—C17—C18—O123.8 (3)
C8—O2—C7—C641.7 (3)O5—S1—C19—C2410.7 (2)
C8—O2—C7—C2−140.3 (2)O4—S1—C19—C24139.72 (18)
C5—C6—C7—O2177.4 (2)N3—S1—C19—C24−105.10 (19)
C5—C6—C7—C2−0.5 (3)O5—S1—C19—C20−168.80 (18)
C3—C2—C7—O2−178.5 (2)O4—S1—C19—C20−39.8 (2)
C1—C2—C7—O21.7 (3)N3—S1—C19—C2075.4 (2)
C3—C2—C7—C6−0.4 (3)C24—C19—C20—C210.6 (3)
C1—C2—C7—C6179.8 (2)S1—C19—C20—C21−179.84 (19)
C7—O2—C8—C9170.55 (19)C19—C20—C21—C22−0.1 (4)
C10—N3—C9—C8−78.4 (3)C20—C21—C22—C23−0.4 (4)
S1—N3—C9—C894.9 (2)C20—C21—C22—C25179.6 (2)
O2—C8—C9—N378.3 (2)C21—C22—C23—C240.3 (4)
C9—N3—C10—C11−70.9 (3)C25—C22—C23—C24−179.6 (2)
S1—N3—C10—C11115.71 (19)C20—C19—C24—C23−0.7 (3)
C12—O3—C11—C10159.53 (19)S1—C19—C24—C23179.78 (18)
N3—C10—C11—O387.7 (2)C22—C23—C24—C190.2 (4)
C11—O3—C12—C1312.5 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C10—H10A···O4i0.972.523.424 (3)154
C20—H20···O4i0.932.393.314 (3)173
C5—H5···O4ii0.932.513.253 (3)137

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2175).

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