organic compounds
3′,6′-Bis(diethylamino)-2-phenylspiro[isoindoline-1,9′-xanthen]-3-one
aKey Laboratory of Analytical Sciences, Ministry of Education, Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, People's Republic of China, and bDepartment of Chemistry, Xiamen University, Xiamen 361005, People's Republic of China
*Correspondence e-mail: hzheng@xmu.edu.cn
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 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); Wu et al. (2007). For a related structure, see: Kwon et al. (2005).
Experimental
Crystal data
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Data collection
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Refinement
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Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
Supporting information
10.1107/S1600536809020248/xu2519sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809020248/xu2519Isup2.hkl
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
(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 (APCI) (positive mode). The molecular peak appeared at a mass/charge ratio of 518.5.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.
Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell
CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).Fig. 1. The molecular structure of the title compound with 30% probability displacement ellipsoids for non-H atoms. |
C34H35N3O2 | F(000) = 1104 |
Mr = 517.65 | Dx = 1.251 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 16600 reflections |
a = 12.0213 (5) Å | θ = 2.4–32.7° |
b = 12.6315 (4) Å | µ = 0.08 mm−1 |
c = 18.9700 (7) Å | T = 173 K |
β = 107.456 (4)° | Block, colourless |
V = 2747.88 (18) Å3 | 0.30 × 0.20 × 0.20 mm |
Z = 4 |
Oxford Diffraction Xcalibur diffractometer with a Sapphire3 (Gemini ultra Mo) detector | 4396 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.025 |
Graphite monochromator | θmax = 26.0°, θmin = 2.4° |
Detector resolution: 16.1903 pixels mm-1 | h = −14→14 |
ϕ and ω scans | k = −15→15 |
29794 measured reflections | l = −21→23 |
5403 independent reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.103 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0572P)2 + 0.4462P] where P = (Fo2 + 2Fc2)/3 |
5403 reflections | (Δ/σ)max = 0.006 |
352 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
C34H35N3O2 | V = 2747.88 (18) Å3 |
Mr = 517.65 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 12.0213 (5) Å | µ = 0.08 mm−1 |
b = 12.6315 (4) Å | T = 173 K |
c = 18.9700 (7) Å | 0.30 × 0.20 × 0.20 mm |
β = 107.456 (4)° |
Oxford Diffraction Xcalibur diffractometer with a Sapphire3 (Gemini ultra Mo) detector | 4396 reflections with I > 2σ(I) |
29794 measured reflections | Rint = 0.025 |
5403 independent reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.103 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.22 e Å−3 |
5403 reflections | Δρmin = −0.19 e Å−3 |
352 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.71114 (11) | 0.71818 (10) | 0.15020 (7) | 0.0228 (3) | |
C2 | 0.82352 (12) | 0.71273 (11) | 0.14514 (8) | 0.0267 (3) | |
H2A | 0.8558 | 0.7722 | 0.1277 | 0.032* | |
C3 | 0.88993 (11) | 0.62080 (11) | 0.16541 (7) | 0.0247 (3) | |
C4 | 0.83537 (12) | 0.53371 (10) | 0.18815 (7) | 0.0240 (3) | |
H4A | 0.8767 | 0.4690 | 0.2011 | 0.029* | |
C5 | 0.72318 (11) | 0.54138 (10) | 0.19186 (7) | 0.0219 (3) | |
H5A | 0.6893 | 0.4815 | 0.2077 | 0.026* | |
C6 | 0.65727 (11) | 0.63372 (10) | 0.17327 (7) | 0.0192 (3) | |
C7 | 0.53398 (11) | 0.64059 (10) | 0.17788 (7) | 0.0192 (3) | |
C8 | 0.48969 (11) | 0.75350 (9) | 0.16449 (7) | 0.0192 (3) | |
C9 | 0.38198 (11) | 0.78341 (10) | 0.17203 (7) | 0.0212 (3) | |
H9A | 0.3381 | 0.7321 | 0.1890 | 0.025* | |
C10 | 0.33646 (11) | 0.88340 (10) | 0.15613 (7) | 0.0225 (3) | |
H10A | 0.2624 | 0.8995 | 0.1617 | 0.027* | |
C11 | 0.39947 (11) | 0.96252 (10) | 0.13143 (7) | 0.0219 (3) | |
C12 | 0.50750 (12) | 0.93349 (10) | 0.12374 (7) | 0.0235 (3) | |
H12A | 0.5524 | 0.9844 | 0.1073 | 0.028* | |
C13 | 0.54985 (11) | 0.83143 (10) | 0.13973 (7) | 0.0214 (3) | |
C14 | 0.44953 (11) | 0.56635 (10) | 0.12430 (7) | 0.0214 (3) | |
C15 | 0.41783 (12) | 0.56501 (11) | 0.04796 (8) | 0.0275 (3) | |
H15A | 0.4507 | 0.6137 | 0.0216 | 0.033* | |
C16 | 0.33642 (13) | 0.49019 (12) | 0.01089 (8) | 0.0340 (4) | |
H16A | 0.3143 | 0.4871 | −0.0415 | 0.041* | |
C17 | 0.28681 (13) | 0.41981 (12) | 0.04928 (9) | 0.0349 (4) | |
H17A | 0.2307 | 0.3698 | 0.0228 | 0.042* | |
C18 | 0.31836 (12) | 0.42201 (11) | 0.12532 (9) | 0.0308 (3) | |
H18A | 0.2847 | 0.3743 | 0.1519 | 0.037* | |
C19 | 0.40063 (11) | 0.49595 (10) | 0.16190 (8) | 0.0235 (3) | |
C20 | 0.45099 (12) | 0.51313 (10) | 0.24234 (8) | 0.0237 (3) | |
C21 | 0.60912 (11) | 0.62493 (10) | 0.31955 (7) | 0.0219 (3) | |
C22 | 0.66767 (14) | 0.54632 (12) | 0.36746 (8) | 0.0341 (3) | |
H22A | 0.6536 | 0.4739 | 0.3542 | 0.041* | |
C23 | 0.74656 (14) | 0.57334 (13) | 0.43449 (8) | 0.0393 (4) | |
H23A | 0.7852 | 0.5192 | 0.4676 | 0.047* | |
C24 | 0.76971 (14) | 0.67813 (13) | 0.45384 (8) | 0.0385 (4) | |
H24A | 0.8240 | 0.6965 | 0.4999 | 0.046* | |
C25 | 0.71330 (15) | 0.75539 (13) | 0.40563 (9) | 0.0439 (4) | |
H25A | 0.7297 | 0.8277 | 0.4182 | 0.053* | |
C26 | 0.63245 (14) | 0.72939 (11) | 0.33859 (8) | 0.0360 (4) | |
H26A | 0.5933 | 0.7838 | 0.3059 | 0.043* | |
C27 | 0.41811 (13) | 1.14312 (11) | 0.08587 (8) | 0.0327 (3) | |
H27A | 0.3609 | 1.1947 | 0.0563 | 0.039* | |
H27B | 0.4559 | 1.1081 | 0.0523 | 0.039* | |
C28 | 0.51015 (15) | 1.20246 (12) | 0.14500 (10) | 0.0418 (4) | |
H28A | 0.5487 | 1.2541 | 0.1216 | 0.063* | |
H28B | 0.5681 | 1.1522 | 0.1740 | 0.063* | |
H28C | 0.4732 | 1.2394 | 0.1776 | 0.063* | |
C29 | 0.25151 (14) | 1.09900 (12) | 0.13220 (9) | 0.0372 (4) | |
H29A | 0.2611 | 1.1744 | 0.1470 | 0.045* | |
H29B | 0.2431 | 1.0579 | 0.1747 | 0.045* | |
C30 | 0.14156 (16) | 1.08697 (19) | 0.06812 (11) | 0.0630 (6) | |
H30A | 0.0747 | 1.1124 | 0.0827 | 0.094* | |
H30B | 0.1302 | 1.0122 | 0.0540 | 0.094* | |
H30C | 0.1485 | 1.1285 | 0.0260 | 0.094* | |
C31 | 1.06594 (13) | 0.70793 (12) | 0.15060 (10) | 0.0379 (4) | |
H31A | 1.1479 | 0.7048 | 0.1825 | 0.045* | |
H31B | 1.0301 | 0.7720 | 0.1646 | 0.045* | |
C32 | 1.06523 (17) | 0.71910 (15) | 0.07113 (10) | 0.0540 (5) | |
H32A | 1.1085 | 0.7829 | 0.0659 | 0.081* | |
H32B | 0.9846 | 0.7248 | 0.0391 | 0.081* | |
H32C | 1.1022 | 0.6569 | 0.0569 | 0.081* | |
C33 | 1.06374 (13) | 0.51390 (12) | 0.17186 (8) | 0.0319 (3) | |
H33A | 1.0513 | 0.4745 | 0.2140 | 0.038* | |
H33B | 1.1485 | 0.5266 | 0.1831 | 0.038* | |
C34 | 1.02314 (13) | 0.44583 (12) | 0.10308 (9) | 0.0364 (4) | |
H34A | 1.0664 | 0.3789 | 0.1113 | 0.055* | |
H34B | 1.0372 | 0.4833 | 0.0613 | 0.055* | |
H34C | 0.9396 | 0.4313 | 0.0922 | 0.055* | |
N1 | 0.35614 (10) | 1.06343 (9) | 0.11526 (7) | 0.0306 (3) | |
N2 | 1.00455 (10) | 0.61526 (10) | 0.16542 (7) | 0.0332 (3) | |
N3 | 0.52732 (9) | 0.59642 (8) | 0.25021 (6) | 0.0205 (2) | |
O1 | 0.65733 (8) | 0.81453 (7) | 0.12950 (6) | 0.0307 (2) | |
O2 | 0.42961 (9) | 0.46357 (8) | 0.29198 (6) | 0.0345 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0214 (7) | 0.0196 (6) | 0.0281 (7) | 0.0008 (5) | 0.0084 (6) | −0.0007 (5) |
C2 | 0.0222 (7) | 0.0232 (7) | 0.0372 (8) | −0.0038 (5) | 0.0128 (6) | −0.0019 (6) |
C3 | 0.0176 (7) | 0.0295 (7) | 0.0257 (7) | 0.0001 (5) | 0.0045 (5) | −0.0075 (6) |
C4 | 0.0218 (7) | 0.0243 (7) | 0.0244 (7) | 0.0057 (5) | 0.0048 (5) | −0.0009 (5) |
C5 | 0.0229 (7) | 0.0223 (7) | 0.0203 (6) | −0.0001 (5) | 0.0064 (5) | 0.0006 (5) |
C6 | 0.0169 (6) | 0.0216 (6) | 0.0188 (6) | −0.0003 (5) | 0.0048 (5) | −0.0016 (5) |
C7 | 0.0177 (6) | 0.0211 (6) | 0.0187 (6) | −0.0007 (5) | 0.0053 (5) | 0.0013 (5) |
C8 | 0.0180 (6) | 0.0198 (6) | 0.0188 (6) | −0.0001 (5) | 0.0040 (5) | −0.0001 (5) |
C9 | 0.0185 (7) | 0.0229 (7) | 0.0221 (6) | −0.0016 (5) | 0.0060 (5) | 0.0013 (5) |
C10 | 0.0169 (6) | 0.0252 (7) | 0.0241 (6) | 0.0025 (5) | 0.0041 (5) | −0.0009 (5) |
C11 | 0.0217 (7) | 0.0204 (6) | 0.0207 (6) | 0.0029 (5) | 0.0019 (5) | 0.0002 (5) |
C12 | 0.0231 (7) | 0.0206 (7) | 0.0275 (7) | −0.0015 (5) | 0.0085 (6) | 0.0036 (5) |
C13 | 0.0180 (7) | 0.0229 (7) | 0.0232 (6) | 0.0007 (5) | 0.0062 (5) | 0.0001 (5) |
C14 | 0.0153 (6) | 0.0205 (6) | 0.0273 (7) | 0.0032 (5) | 0.0049 (5) | −0.0040 (5) |
C15 | 0.0227 (7) | 0.0306 (7) | 0.0285 (7) | 0.0033 (6) | 0.0068 (6) | −0.0008 (6) |
C16 | 0.0259 (8) | 0.0414 (9) | 0.0286 (7) | 0.0081 (6) | −0.0012 (6) | −0.0116 (6) |
C17 | 0.0207 (7) | 0.0287 (8) | 0.0492 (9) | −0.0006 (6) | 0.0015 (7) | −0.0164 (7) |
C18 | 0.0219 (7) | 0.0220 (7) | 0.0483 (9) | 0.0001 (6) | 0.0100 (6) | −0.0046 (6) |
C19 | 0.0181 (7) | 0.0194 (6) | 0.0334 (7) | 0.0035 (5) | 0.0083 (6) | −0.0026 (5) |
C20 | 0.0217 (7) | 0.0186 (6) | 0.0341 (7) | 0.0024 (5) | 0.0132 (6) | 0.0022 (5) |
C21 | 0.0197 (7) | 0.0269 (7) | 0.0197 (6) | 0.0037 (5) | 0.0071 (5) | −0.0011 (5) |
C22 | 0.0398 (9) | 0.0287 (8) | 0.0311 (8) | 0.0039 (7) | 0.0065 (7) | 0.0052 (6) |
C23 | 0.0395 (9) | 0.0459 (10) | 0.0277 (8) | 0.0082 (7) | 0.0029 (7) | 0.0120 (7) |
C24 | 0.0360 (9) | 0.0513 (10) | 0.0233 (7) | 0.0056 (7) | 0.0014 (6) | −0.0050 (7) |
C25 | 0.0471 (10) | 0.0341 (9) | 0.0377 (9) | 0.0041 (7) | −0.0069 (8) | −0.0114 (7) |
C26 | 0.0410 (9) | 0.0259 (7) | 0.0318 (8) | 0.0069 (6) | −0.0033 (7) | 0.0000 (6) |
C27 | 0.0348 (8) | 0.0229 (7) | 0.0407 (8) | 0.0070 (6) | 0.0118 (7) | 0.0098 (6) |
C28 | 0.0411 (10) | 0.0309 (8) | 0.0529 (10) | 0.0000 (7) | 0.0131 (8) | 0.0054 (7) |
C29 | 0.0386 (9) | 0.0259 (7) | 0.0519 (10) | 0.0125 (7) | 0.0209 (8) | 0.0079 (7) |
C30 | 0.0363 (10) | 0.0903 (16) | 0.0623 (12) | 0.0247 (10) | 0.0148 (9) | 0.0299 (11) |
C31 | 0.0181 (7) | 0.0366 (9) | 0.0593 (11) | −0.0060 (6) | 0.0123 (7) | −0.0130 (7) |
C32 | 0.0554 (12) | 0.0458 (10) | 0.0569 (11) | −0.0162 (9) | 0.0110 (9) | 0.0081 (9) |
C33 | 0.0193 (7) | 0.0420 (9) | 0.0339 (8) | 0.0091 (6) | 0.0075 (6) | 0.0021 (6) |
C34 | 0.0303 (8) | 0.0384 (8) | 0.0430 (9) | 0.0028 (7) | 0.0149 (7) | −0.0043 (7) |
N1 | 0.0279 (7) | 0.0227 (6) | 0.0424 (7) | 0.0074 (5) | 0.0123 (6) | 0.0073 (5) |
N2 | 0.0184 (6) | 0.0320 (7) | 0.0504 (8) | 0.0006 (5) | 0.0123 (6) | −0.0056 (6) |
N3 | 0.0212 (6) | 0.0196 (5) | 0.0215 (5) | −0.0002 (4) | 0.0075 (4) | 0.0022 (4) |
O1 | 0.0242 (5) | 0.0210 (5) | 0.0540 (7) | 0.0036 (4) | 0.0225 (5) | 0.0089 (4) |
O2 | 0.0385 (6) | 0.0315 (6) | 0.0391 (6) | −0.0055 (5) | 0.0202 (5) | 0.0072 (4) |
C1—O1 | 1.3789 (15) | C21—C22 | 1.3870 (19) |
C1—C2 | 1.3846 (19) | C21—N3 | 1.4320 (16) |
C1—C6 | 1.3854 (18) | C22—C23 | 1.382 (2) |
C2—C3 | 1.3961 (19) | C22—H22A | 0.9500 |
C2—H2A | 0.9500 | C23—C24 | 1.380 (2) |
C3—N2 | 1.3796 (18) | C23—H23A | 0.9500 |
C3—C4 | 1.413 (2) | C24—C25 | 1.370 (2) |
C4—C5 | 1.3749 (19) | C24—H24A | 0.9500 |
C4—H4A | 0.9500 | C25—C26 | 1.389 (2) |
C5—C6 | 1.3945 (18) | C25—H25A | 0.9500 |
C5—H5A | 0.9500 | C26—H26A | 0.9500 |
C6—C7 | 1.5131 (18) | C27—N1 | 1.4588 (19) |
C7—N3 | 1.5054 (16) | C27—C28 | 1.516 (2) |
C7—C8 | 1.5170 (17) | C27—H27A | 0.9900 |
C7—C14 | 1.5245 (17) | C27—H27B | 0.9900 |
C8—C13 | 1.3842 (18) | C28—H28A | 0.9800 |
C8—C9 | 1.3967 (18) | C28—H28B | 0.9800 |
C9—C10 | 1.3735 (18) | C28—H28C | 0.9800 |
C9—H9A | 0.9500 | C29—N1 | 1.4593 (19) |
C10—C11 | 1.4161 (19) | C29—C30 | 1.511 (3) |
C10—H10A | 0.9500 | C29—H29A | 0.9900 |
C11—N1 | 1.3763 (17) | C29—H29B | 0.9900 |
C11—C12 | 1.3985 (19) | C30—H30A | 0.9800 |
C12—C13 | 1.3858 (18) | C30—H30B | 0.9800 |
C12—H12A | 0.9500 | C30—H30C | 0.9800 |
C13—O1 | 1.3795 (16) | C31—N2 | 1.4555 (19) |
C14—C19 | 1.3773 (19) | C31—C32 | 1.512 (3) |
C14—C15 | 1.3826 (19) | C31—H31A | 0.9900 |
C15—C16 | 1.390 (2) | C31—H31B | 0.9900 |
C15—H15A | 0.9500 | C32—H32A | 0.9800 |
C16—C17 | 1.392 (2) | C32—H32B | 0.9800 |
C16—H16A | 0.9500 | C32—H32C | 0.9800 |
C17—C18 | 1.377 (2) | C33—N2 | 1.4520 (18) |
C17—H17A | 0.9500 | C33—C34 | 1.516 (2) |
C18—C19 | 1.3858 (19) | C33—H33A | 0.9900 |
C18—H18A | 0.9500 | C33—H33B | 0.9900 |
C19—C20 | 1.4790 (19) | C34—H34A | 0.9800 |
C20—O2 | 1.2207 (16) | C34—H34B | 0.9800 |
C20—N3 | 1.3744 (17) | C34—H34C | 0.9800 |
C21—C26 | 1.3744 (19) | ||
O1—C1—C2 | 114.10 (11) | C24—C23—H23A | 119.7 |
O1—C1—C6 | 123.08 (12) | C22—C23—H23A | 119.7 |
C2—C1—C6 | 122.81 (12) | C25—C24—C23 | 119.08 (14) |
C1—C2—C3 | 120.76 (12) | C25—C24—H24A | 120.5 |
C1—C2—H2A | 119.6 | C23—C24—H24A | 120.5 |
C3—C2—H2A | 119.6 | C24—C25—C26 | 120.88 (15) |
N2—C3—C2 | 122.06 (13) | C24—C25—H25A | 119.6 |
N2—C3—C4 | 121.03 (12) | C26—C25—H25A | 119.6 |
C2—C3—C4 | 116.88 (12) | C21—C26—C25 | 119.95 (13) |
C5—C4—C3 | 120.87 (12) | C21—C26—H26A | 120.0 |
C5—C4—H4A | 119.6 | C25—C26—H26A | 120.0 |
C3—C4—H4A | 119.6 | N1—C27—C28 | 113.66 (13) |
C4—C5—C6 | 122.52 (12) | N1—C27—H27A | 108.8 |
C4—C5—H5A | 118.7 | C28—C27—H27A | 108.8 |
C6—C5—H5A | 118.7 | N1—C27—H27B | 108.8 |
C1—C6—C5 | 116.11 (12) | C28—C27—H27B | 108.8 |
C1—C6—C7 | 122.20 (11) | H27A—C27—H27B | 107.7 |
C5—C6—C7 | 121.69 (11) | C27—C28—H28A | 109.5 |
N3—C7—C6 | 110.63 (10) | C27—C28—H28B | 109.5 |
N3—C7—C8 | 112.90 (10) | H28A—C28—H28B | 109.5 |
C6—C7—C8 | 110.18 (10) | C27—C28—H28C | 109.5 |
N3—C7—C14 | 99.96 (10) | H28A—C28—H28C | 109.5 |
C6—C7—C14 | 113.21 (10) | H28B—C28—H28C | 109.5 |
C8—C7—C14 | 109.67 (10) | N1—C29—C30 | 113.30 (15) |
C13—C8—C9 | 115.92 (11) | N1—C29—H29A | 108.9 |
C13—C8—C7 | 122.18 (12) | C30—C29—H29A | 108.9 |
C9—C8—C7 | 121.79 (11) | N1—C29—H29B | 108.9 |
C10—C9—C8 | 123.15 (12) | C30—C29—H29B | 108.9 |
C10—C9—H9A | 118.4 | H29A—C29—H29B | 107.7 |
C8—C9—H9A | 118.4 | C29—C30—H30A | 109.5 |
C9—C10—C11 | 120.28 (12) | C29—C30—H30B | 109.5 |
C9—C10—H10A | 119.9 | H30A—C30—H30B | 109.5 |
C11—C10—H10A | 119.9 | C29—C30—H30C | 109.5 |
N1—C11—C12 | 121.39 (12) | H30A—C30—H30C | 109.5 |
N1—C11—C10 | 121.54 (12) | H30B—C30—H30C | 109.5 |
C12—C11—C10 | 117.07 (11) | N2—C31—C32 | 114.59 (13) |
C13—C12—C11 | 120.85 (12) | N2—C31—H31A | 108.6 |
C13—C12—H12A | 119.6 | C32—C31—H31A | 108.6 |
C11—C12—H12A | 119.6 | N2—C31—H31B | 108.6 |
O1—C13—C8 | 122.99 (11) | C32—C31—H31B | 108.6 |
O1—C13—C12 | 114.28 (11) | H31A—C31—H31B | 107.6 |
C8—C13—C12 | 122.73 (12) | C31—C32—H32A | 109.5 |
C19—C14—C15 | 120.55 (12) | C31—C32—H32B | 109.5 |
C19—C14—C7 | 110.74 (11) | H32A—C32—H32B | 109.5 |
C15—C14—C7 | 128.69 (12) | C31—C32—H32C | 109.5 |
C14—C15—C16 | 117.98 (14) | H32A—C32—H32C | 109.5 |
C14—C15—H15A | 121.0 | H32B—C32—H32C | 109.5 |
C16—C15—H15A | 121.0 | N2—C33—C34 | 113.87 (12) |
C15—C16—C17 | 121.11 (14) | N2—C33—H33A | 108.8 |
C15—C16—H16A | 119.4 | C34—C33—H33A | 108.8 |
C17—C16—H16A | 119.4 | N2—C33—H33B | 108.8 |
C18—C17—C16 | 120.57 (13) | C34—C33—H33B | 108.8 |
C18—C17—H17A | 119.7 | H33A—C33—H33B | 107.7 |
C16—C17—H17A | 119.7 | C33—C34—H34A | 109.5 |
C17—C18—C19 | 117.97 (14) | C33—C34—H34B | 109.5 |
C17—C18—H18A | 121.0 | H34A—C34—H34B | 109.5 |
C19—C18—H18A | 121.0 | C33—C34—H34C | 109.5 |
C14—C19—C18 | 121.81 (13) | H34A—C34—H34C | 109.5 |
C14—C19—C20 | 109.47 (11) | H34B—C34—H34C | 109.5 |
C18—C19—C20 | 128.71 (13) | C11—N1—C27 | 121.45 (12) |
O2—C20—N3 | 126.65 (13) | C11—N1—C29 | 121.98 (12) |
O2—C20—C19 | 127.22 (13) | C27—N1—C29 | 116.38 (11) |
N3—C20—C19 | 106.13 (11) | C3—N2—C33 | 120.59 (12) |
C26—C21—C22 | 119.45 (13) | C3—N2—C31 | 121.56 (12) |
C26—C21—N3 | 120.83 (12) | C33—N2—C31 | 117.48 (12) |
C22—C21—N3 | 119.70 (12) | C20—N3—C21 | 122.99 (11) |
C23—C22—C21 | 119.97 (14) | C20—N3—C7 | 113.63 (10) |
C23—C22—H22A | 120.0 | C21—N3—C7 | 122.30 (10) |
C21—C22—H22A | 120.0 | C1—O1—C13 | 118.40 (10) |
C24—C23—C22 | 120.65 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
C31—H31B···O2i | 0.99 | 2.56 | 3.4032 (19) | 144 |
Symmetry code: (i) −x+3/2, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C34H35N3O2 |
Mr | 517.65 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 173 |
a, b, c (Å) | 12.0213 (5), 12.6315 (4), 18.9700 (7) |
β (°) | 107.456 (4) |
V (Å3) | 2747.88 (18) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.30 × 0.20 × 0.20 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur diffractometer with a Sapphire3 (Gemini ultra Mo) detector |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 29794, 5403, 4396 |
Rint | 0.025 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.103, 1.06 |
No. of reflections | 5403 |
No. of parameters | 352 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.22, −0.19 |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).
D—H···A | D—H | H···A | D···A | D—H···A |
C31—H31B···O2i | 0.99 | 2.56 | 3.4032 (19) | 144 |
Symmetry code: (i) −x+3/2, y+1/2, −z+1/2. |
Acknowledgements
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.
References
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
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.