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Acta Crystallogr Sect E Struct Rep Online. 2009 July 1; 65(Pt 7): o1464.
Published online 2009 June 6. doi:  10.1107/S1600536809020248
PMCID: PMC2969317

3′,6′-Bis(diethyl­amino)-2-phenyl­spiro[isoindoline-1,9′-xanthen]-3-one

Abstract

The title compound, C34H35O2N3, was synthesized by the reaction of 2-[3,6-bis­(diethyl­amino)-9H-xanthen-9-yl]benzoyl chloride with aniline. In the mol­ecular structure, the dihedral angles between the isoindoline and xanthene planes and between the isoindoline and benzene planes are 86.9 (3) and 47.0 (2)°, respectively. The mol­ecular packing in the crystal structure is stabilized by weak C—H(...)O hydrogen bonding.

Related literature

For applications of rhodamine-based dyes as probes and sensors, see: Zheng et al. (2008 [triangle]); Wu et al. (2007 [triangle]). For a related structure, see: Kwon et al. (2005 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1464-scheme1.jpg

Experimental

Crystal data

  • C34H35N3O2
  • M r = 517.65
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1464-efi1.jpg
  • a = 12.0213 (5) Å
  • b = 12.6315 (4) Å
  • c = 18.9700 (7) Å
  • β = 107.456 (4)°
  • V = 2747.88 (18) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 173 K
  • 0.30 × 0.20 × 0.20 mm

Data collection

  • Oxford Diffraction Xcalibur diffractometer with a Sapphire3 (Gemini Ultra Mo) detector
  • Absorption correction: none
  • 29794 measured reflections
  • 5403 independent reflections
  • 4396 reflections with I > 2σ(I)
  • R int = 0.025

Refinement

  • R[F 2 > 2σ(F 2)] = 0.040
  • wR(F 2) = 0.103
  • S = 1.06
  • 5403 reflections
  • 352 parameters
  • H-atom parameters constrained
  • Δρmax = 0.22 e Å−3
  • Δρmin = −0.19 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 [triangle]); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 [triangle]); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809020248/xu2519sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809020248/xu2519Isup2.hkl

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

Acknowledgments

The authors thank the Science Research Foundation of Xiamen University (grant No. E43011) and the National Natural Science Foundation of China (grant No. 20675067) for supporting this work. We also thank Mr S.-Y. Yang and Mr Z.-B. Wei for technical assistance.

supplementary crystallographic information

Comment

Rhodamine-based dyes, known by their excellent spectroscopic properties of large molar extinction coefficient and high fluorescence quantum yield (Wu et al., 2007), have found applications in the study of complex biological systems and environmental analysis as molecular probes. In the present paper, the structure of title compound has been determined as part of a research program involving the synthesis and nitric oxide sensing (Zheng et al., 2008).

The molecular structure is depicted in Fig. 1. Bond lengths and angles are in good agreement with previous reported for similar compounds (Kwon et al., 2005). The dihedral angle between isoindoline and xanthene mean planes is 86.9 (3)° The dihedral angle between the isoindoline and benzene ring mean planes is 47.0 (2)°. Weak C—H···O hydrogen bonding (Table 1) helps to stabilize the crystal structure.

Experimental

To a solution of 3',6'-bis(diethylamino)-3H-spiro[isobenzofuran-1,9'- xanthen]-3-one (1.3 g, 2.8 mmol) in dry 1,2-dichloroethane (10.0 ml) at room temperature, phosphorus oxychloride (1.4 g, 8.4 mmol) was added dropwise over a period of 5 min. After being refluxed for 4 h, the reaction mixture was cooled and concentrated under vacuum to give 2-(3,6-bis(diethylamino)-9H-xanthen-9-yl)benzoyl chloride. The chloride salt was dissolved in dry acetonitrile (12.0 ml). This solution was added dropwise to a solution of aniline (1.6 g, 17.5 mmol) in dry acetonitrile (7.5 ml) containing triethylamine (10.0 ml). After stirring for 4 h at room temperature, the mixture was concentrated under vacuum and the crude product was purified by column chromatography (ethyl acetate/dichloromethane, 1:20) to give the title compound as a white solid in 72% yield. Single crystals of the title compound were obtained by slow evaporation of a dichloromethane/methanol solution (5:1 v/v). The product was analyzed by atmospheric-Pressure Chemical Ionization (APCI) mass spectrometry (positive mode). The molecular peak appeared at a mass/charge ratio of 518.5.

Refinement

H atoms were placed geometrically with C—H = 0.95 (aromatic), 0.98 (methyl) and 0.99 Å (methylene), and refined using a riding atom model with Uiso(H) = 1.5Ueq(C) for methyl and 1.2Ueq(C) for the others.

Figures

Fig. 1.
The molecular structure of the title compound with 30% probability displacement ellipsoids for non-H atoms.

Crystal data

C34H35N3O2F(000) = 1104
Mr = 517.65Dx = 1.251 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 16600 reflections
a = 12.0213 (5) Åθ = 2.4–32.7°
b = 12.6315 (4) ŵ = 0.08 mm1
c = 18.9700 (7) ÅT = 173 K
β = 107.456 (4)°Block, colourless
V = 2747.88 (18) Å30.30 × 0.20 × 0.20 mm
Z = 4

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire3 (Gemini ultra Mo) detector4396 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.025
graphiteθmax = 26.0°, θmin = 2.4°
Detector resolution: 16.1903 pixels mm-1h = −14→14
[var phi] and ω scansk = −15→15
29794 measured reflectionsl = −21→23
5403 independent reflections

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)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103H-atom parameters constrained
S = 1.06w = 1/[σ2(Fo2) + (0.0572P)2 + 0.4462P] where P = (Fo2 + 2Fc2)/3
5403 reflections(Δ/σ)max = 0.006
352 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = −0.19 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
C10.71114 (11)0.71818 (10)0.15020 (7)0.0228 (3)
C20.82352 (12)0.71273 (11)0.14514 (8)0.0267 (3)
H2A0.85580.77220.12770.032*
C30.88993 (11)0.62080 (11)0.16541 (7)0.0247 (3)
C40.83537 (12)0.53371 (10)0.18815 (7)0.0240 (3)
H4A0.87670.46900.20110.029*
C50.72318 (11)0.54138 (10)0.19186 (7)0.0219 (3)
H5A0.68930.48150.20770.026*
C60.65727 (11)0.63372 (10)0.17327 (7)0.0192 (3)
C70.53398 (11)0.64059 (10)0.17788 (7)0.0192 (3)
C80.48969 (11)0.75350 (9)0.16449 (7)0.0192 (3)
C90.38198 (11)0.78341 (10)0.17203 (7)0.0212 (3)
H9A0.33810.73210.18900.025*
C100.33646 (11)0.88340 (10)0.15613 (7)0.0225 (3)
H10A0.26240.89950.16170.027*
C110.39947 (11)0.96252 (10)0.13143 (7)0.0219 (3)
C120.50750 (12)0.93349 (10)0.12374 (7)0.0235 (3)
H12A0.55240.98440.10730.028*
C130.54985 (11)0.83143 (10)0.13973 (7)0.0214 (3)
C140.44953 (11)0.56635 (10)0.12430 (7)0.0214 (3)
C150.41783 (12)0.56501 (11)0.04796 (8)0.0275 (3)
H15A0.45070.61370.02160.033*
C160.33642 (13)0.49019 (12)0.01089 (8)0.0340 (4)
H16A0.31430.4871−0.04150.041*
C170.28681 (13)0.41981 (12)0.04928 (9)0.0349 (4)
H17A0.23070.36980.02280.042*
C180.31836 (12)0.42201 (11)0.12532 (9)0.0308 (3)
H18A0.28470.37430.15190.037*
C190.40063 (11)0.49595 (10)0.16190 (8)0.0235 (3)
C200.45099 (12)0.51313 (10)0.24234 (8)0.0237 (3)
C210.60912 (11)0.62493 (10)0.31955 (7)0.0219 (3)
C220.66767 (14)0.54632 (12)0.36746 (8)0.0341 (3)
H22A0.65360.47390.35420.041*
C230.74656 (14)0.57334 (13)0.43449 (8)0.0393 (4)
H23A0.78520.51920.46760.047*
C240.76971 (14)0.67813 (13)0.45384 (8)0.0385 (4)
H24A0.82400.69650.49990.046*
C250.71330 (15)0.75539 (13)0.40563 (9)0.0439 (4)
H25A0.72970.82770.41820.053*
C260.63245 (14)0.72939 (11)0.33859 (8)0.0360 (4)
H26A0.59330.78380.30590.043*
C270.41811 (13)1.14312 (11)0.08587 (8)0.0327 (3)
H27A0.36091.19470.05630.039*
H27B0.45591.10810.05230.039*
C280.51015 (15)1.20246 (12)0.14500 (10)0.0418 (4)
H28A0.54871.25410.12160.063*
H28B0.56811.15220.17400.063*
H28C0.47321.23940.17760.063*
C290.25151 (14)1.09900 (12)0.13220 (9)0.0372 (4)
H29A0.26111.17440.14700.045*
H29B0.24311.05790.17470.045*
C300.14156 (16)1.08697 (19)0.06812 (11)0.0630 (6)
H30A0.07471.11240.08270.094*
H30B0.13021.01220.05400.094*
H30C0.14851.12850.02600.094*
C311.06594 (13)0.70793 (12)0.15060 (10)0.0379 (4)
H31A1.14790.70480.18250.045*
H31B1.03010.77200.16460.045*
C321.06523 (17)0.71910 (15)0.07113 (10)0.0540 (5)
H32A1.10850.78290.06590.081*
H32B0.98460.72480.03910.081*
H32C1.10220.65690.05690.081*
C331.06374 (13)0.51390 (12)0.17186 (8)0.0319 (3)
H33A1.05130.47450.21400.038*
H33B1.14850.52660.18310.038*
C341.02314 (13)0.44583 (12)0.10308 (9)0.0364 (4)
H34A1.06640.37890.11130.055*
H34B1.03720.48330.06130.055*
H34C0.93960.43130.09220.055*
N10.35614 (10)1.06343 (9)0.11526 (7)0.0306 (3)
N21.00455 (10)0.61526 (10)0.16542 (7)0.0332 (3)
N30.52732 (9)0.59642 (8)0.25021 (6)0.0205 (2)
O10.65733 (8)0.81453 (7)0.12950 (6)0.0307 (2)
O20.42961 (9)0.46357 (8)0.29198 (6)0.0345 (3)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0214 (7)0.0196 (6)0.0281 (7)0.0008 (5)0.0084 (6)−0.0007 (5)
C20.0222 (7)0.0232 (7)0.0372 (8)−0.0038 (5)0.0128 (6)−0.0019 (6)
C30.0176 (7)0.0295 (7)0.0257 (7)0.0001 (5)0.0045 (5)−0.0075 (6)
C40.0218 (7)0.0243 (7)0.0244 (7)0.0057 (5)0.0048 (5)−0.0009 (5)
C50.0229 (7)0.0223 (7)0.0203 (6)−0.0001 (5)0.0064 (5)0.0006 (5)
C60.0169 (6)0.0216 (6)0.0188 (6)−0.0003 (5)0.0048 (5)−0.0016 (5)
C70.0177 (6)0.0211 (6)0.0187 (6)−0.0007 (5)0.0053 (5)0.0013 (5)
C80.0180 (6)0.0198 (6)0.0188 (6)−0.0001 (5)0.0040 (5)−0.0001 (5)
C90.0185 (7)0.0229 (7)0.0221 (6)−0.0016 (5)0.0060 (5)0.0013 (5)
C100.0169 (6)0.0252 (7)0.0241 (6)0.0025 (5)0.0041 (5)−0.0009 (5)
C110.0217 (7)0.0204 (6)0.0207 (6)0.0029 (5)0.0019 (5)0.0002 (5)
C120.0231 (7)0.0206 (7)0.0275 (7)−0.0015 (5)0.0085 (6)0.0036 (5)
C130.0180 (7)0.0229 (7)0.0232 (6)0.0007 (5)0.0062 (5)0.0001 (5)
C140.0153 (6)0.0205 (6)0.0273 (7)0.0032 (5)0.0049 (5)−0.0040 (5)
C150.0227 (7)0.0306 (7)0.0285 (7)0.0033 (6)0.0068 (6)−0.0008 (6)
C160.0259 (8)0.0414 (9)0.0286 (7)0.0081 (6)−0.0012 (6)−0.0116 (6)
C170.0207 (7)0.0287 (8)0.0492 (9)−0.0006 (6)0.0015 (7)−0.0164 (7)
C180.0219 (7)0.0220 (7)0.0483 (9)0.0001 (6)0.0100 (6)−0.0046 (6)
C190.0181 (7)0.0194 (6)0.0334 (7)0.0035 (5)0.0083 (6)−0.0026 (5)
C200.0217 (7)0.0186 (6)0.0341 (7)0.0024 (5)0.0132 (6)0.0022 (5)
C210.0197 (7)0.0269 (7)0.0197 (6)0.0037 (5)0.0071 (5)−0.0011 (5)
C220.0398 (9)0.0287 (8)0.0311 (8)0.0039 (7)0.0065 (7)0.0052 (6)
C230.0395 (9)0.0459 (10)0.0277 (8)0.0082 (7)0.0029 (7)0.0120 (7)
C240.0360 (9)0.0513 (10)0.0233 (7)0.0056 (7)0.0014 (6)−0.0050 (7)
C250.0471 (10)0.0341 (9)0.0377 (9)0.0041 (7)−0.0069 (8)−0.0114 (7)
C260.0410 (9)0.0259 (7)0.0318 (8)0.0069 (6)−0.0033 (7)0.0000 (6)
C270.0348 (8)0.0229 (7)0.0407 (8)0.0070 (6)0.0118 (7)0.0098 (6)
C280.0411 (10)0.0309 (8)0.0529 (10)0.0000 (7)0.0131 (8)0.0054 (7)
C290.0386 (9)0.0259 (7)0.0519 (10)0.0125 (7)0.0209 (8)0.0079 (7)
C300.0363 (10)0.0903 (16)0.0623 (12)0.0247 (10)0.0148 (9)0.0299 (11)
C310.0181 (7)0.0366 (9)0.0593 (11)−0.0060 (6)0.0123 (7)−0.0130 (7)
C320.0554 (12)0.0458 (10)0.0569 (11)−0.0162 (9)0.0110 (9)0.0081 (9)
C330.0193 (7)0.0420 (9)0.0339 (8)0.0091 (6)0.0075 (6)0.0021 (6)
C340.0303 (8)0.0384 (8)0.0430 (9)0.0028 (7)0.0149 (7)−0.0043 (7)
N10.0279 (7)0.0227 (6)0.0424 (7)0.0074 (5)0.0123 (6)0.0073 (5)
N20.0184 (6)0.0320 (7)0.0504 (8)0.0006 (5)0.0123 (6)−0.0056 (6)
N30.0212 (6)0.0196 (5)0.0215 (5)−0.0002 (4)0.0075 (4)0.0022 (4)
O10.0242 (5)0.0210 (5)0.0540 (7)0.0036 (4)0.0225 (5)0.0089 (4)
O20.0385 (6)0.0315 (6)0.0391 (6)−0.0055 (5)0.0202 (5)0.0072 (4)

Geometric parameters (Å, °)

C1—O11.3789 (15)C21—C221.3870 (19)
C1—C21.3846 (19)C21—N31.4320 (16)
C1—C61.3854 (18)C22—C231.382 (2)
C2—C31.3961 (19)C22—H22A0.9500
C2—H2A0.9500C23—C241.380 (2)
C3—N21.3796 (18)C23—H23A0.9500
C3—C41.413 (2)C24—C251.370 (2)
C4—C51.3749 (19)C24—H24A0.9500
C4—H4A0.9500C25—C261.389 (2)
C5—C61.3945 (18)C25—H25A0.9500
C5—H5A0.9500C26—H26A0.9500
C6—C71.5131 (18)C27—N11.4588 (19)
C7—N31.5054 (16)C27—C281.516 (2)
C7—C81.5170 (17)C27—H27A0.9900
C7—C141.5245 (17)C27—H27B0.9900
C8—C131.3842 (18)C28—H28A0.9800
C8—C91.3967 (18)C28—H28B0.9800
C9—C101.3735 (18)C28—H28C0.9800
C9—H9A0.9500C29—N11.4593 (19)
C10—C111.4161 (19)C29—C301.511 (3)
C10—H10A0.9500C29—H29A0.9900
C11—N11.3763 (17)C29—H29B0.9900
C11—C121.3985 (19)C30—H30A0.9800
C12—C131.3858 (18)C30—H30B0.9800
C12—H12A0.9500C30—H30C0.9800
C13—O11.3795 (16)C31—N21.4555 (19)
C14—C191.3773 (19)C31—C321.512 (3)
C14—C151.3826 (19)C31—H31A0.9900
C15—C161.390 (2)C31—H31B0.9900
C15—H15A0.9500C32—H32A0.9800
C16—C171.392 (2)C32—H32B0.9800
C16—H16A0.9500C32—H32C0.9800
C17—C181.377 (2)C33—N21.4520 (18)
C17—H17A0.9500C33—C341.516 (2)
C18—C191.3858 (19)C33—H33A0.9900
C18—H18A0.9500C33—H33B0.9900
C19—C201.4790 (19)C34—H34A0.9800
C20—O21.2207 (16)C34—H34B0.9800
C20—N31.3744 (17)C34—H34C0.9800
C21—C261.3744 (19)
O1—C1—C2114.10 (11)C24—C23—H23A119.7
O1—C1—C6123.08 (12)C22—C23—H23A119.7
C2—C1—C6122.81 (12)C25—C24—C23119.08 (14)
C1—C2—C3120.76 (12)C25—C24—H24A120.5
C1—C2—H2A119.6C23—C24—H24A120.5
C3—C2—H2A119.6C24—C25—C26120.88 (15)
N2—C3—C2122.06 (13)C24—C25—H25A119.6
N2—C3—C4121.03 (12)C26—C25—H25A119.6
C2—C3—C4116.88 (12)C21—C26—C25119.95 (13)
C5—C4—C3120.87 (12)C21—C26—H26A120.0
C5—C4—H4A119.6C25—C26—H26A120.0
C3—C4—H4A119.6N1—C27—C28113.66 (13)
C4—C5—C6122.52 (12)N1—C27—H27A108.8
C4—C5—H5A118.7C28—C27—H27A108.8
C6—C5—H5A118.7N1—C27—H27B108.8
C1—C6—C5116.11 (12)C28—C27—H27B108.8
C1—C6—C7122.20 (11)H27A—C27—H27B107.7
C5—C6—C7121.69 (11)C27—C28—H28A109.5
N3—C7—C6110.63 (10)C27—C28—H28B109.5
N3—C7—C8112.90 (10)H28A—C28—H28B109.5
C6—C7—C8110.18 (10)C27—C28—H28C109.5
N3—C7—C1499.96 (10)H28A—C28—H28C109.5
C6—C7—C14113.21 (10)H28B—C28—H28C109.5
C8—C7—C14109.67 (10)N1—C29—C30113.30 (15)
C13—C8—C9115.92 (11)N1—C29—H29A108.9
C13—C8—C7122.18 (12)C30—C29—H29A108.9
C9—C8—C7121.79 (11)N1—C29—H29B108.9
C10—C9—C8123.15 (12)C30—C29—H29B108.9
C10—C9—H9A118.4H29A—C29—H29B107.7
C8—C9—H9A118.4C29—C30—H30A109.5
C9—C10—C11120.28 (12)C29—C30—H30B109.5
C9—C10—H10A119.9H30A—C30—H30B109.5
C11—C10—H10A119.9C29—C30—H30C109.5
N1—C11—C12121.39 (12)H30A—C30—H30C109.5
N1—C11—C10121.54 (12)H30B—C30—H30C109.5
C12—C11—C10117.07 (11)N2—C31—C32114.59 (13)
C13—C12—C11120.85 (12)N2—C31—H31A108.6
C13—C12—H12A119.6C32—C31—H31A108.6
C11—C12—H12A119.6N2—C31—H31B108.6
O1—C13—C8122.99 (11)C32—C31—H31B108.6
O1—C13—C12114.28 (11)H31A—C31—H31B107.6
C8—C13—C12122.73 (12)C31—C32—H32A109.5
C19—C14—C15120.55 (12)C31—C32—H32B109.5
C19—C14—C7110.74 (11)H32A—C32—H32B109.5
C15—C14—C7128.69 (12)C31—C32—H32C109.5
C14—C15—C16117.98 (14)H32A—C32—H32C109.5
C14—C15—H15A121.0H32B—C32—H32C109.5
C16—C15—H15A121.0N2—C33—C34113.87 (12)
C15—C16—C17121.11 (14)N2—C33—H33A108.8
C15—C16—H16A119.4C34—C33—H33A108.8
C17—C16—H16A119.4N2—C33—H33B108.8
C18—C17—C16120.57 (13)C34—C33—H33B108.8
C18—C17—H17A119.7H33A—C33—H33B107.7
C16—C17—H17A119.7C33—C34—H34A109.5
C17—C18—C19117.97 (14)C33—C34—H34B109.5
C17—C18—H18A121.0H34A—C34—H34B109.5
C19—C18—H18A121.0C33—C34—H34C109.5
C14—C19—C18121.81 (13)H34A—C34—H34C109.5
C14—C19—C20109.47 (11)H34B—C34—H34C109.5
C18—C19—C20128.71 (13)C11—N1—C27121.45 (12)
O2—C20—N3126.65 (13)C11—N1—C29121.98 (12)
O2—C20—C19127.22 (13)C27—N1—C29116.38 (11)
N3—C20—C19106.13 (11)C3—N2—C33120.59 (12)
C26—C21—C22119.45 (13)C3—N2—C31121.56 (12)
C26—C21—N3120.83 (12)C33—N2—C31117.48 (12)
C22—C21—N3119.70 (12)C20—N3—C21122.99 (11)
C23—C22—C21119.97 (14)C20—N3—C7113.63 (10)
C23—C22—H22A120.0C21—N3—C7122.30 (10)
C21—C22—H22A120.0C1—O1—C13118.40 (10)
C24—C23—C22120.65 (14)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C31—H31B···O2i0.992.563.4032 (19)144

Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2519).

References

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