organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

[4-(1-Benzo­furan-2-yl)phen­yl]di­phenyl­amine

aCardinal Tien College of Healthcare & Management, Taipei, Taiwan 231, and bInstitute of Chemistry, Academia Sinica, Nankang, Taipei, Taiwan
*Correspondence e-mail: pshuang@ctcn.edu.tw

(Received 4 November 2010; accepted 2 December 2010; online 11 December 2010)

The asymmetric unit of the title compound, C26H19NO, contains two mol­ecules. The dihedral angles between the benzofuran and benzene rings are 5.09 (8), 59.02 (8) and 67.74 (8)° in one mol­ecule and 18.70 (8), 52.78 (8) and 41.74 (8)° in the other. Weak inter­molecular C—H⋯π inter­actions help to stabilize the molecular structure .

Related literature

The title compound is a precursor for the production of hole transporting and/or emitting materials, see: Shen et al. (2005[Shen, J. Y., Lee, C. Y., Huang, T.-H., Lin, J. T., Tao, Y.-T., Chien, C.-H. & Tsai, C. (2005). J. Mater. Chem. 15, 2455-2463.]). For lone-pair delocalization, see: Wang et al. (2001[Wang, X. M., Wang, D., Zhou, G. Y., Yu, W. T., Zhou, Y. F., Fang, Q. & Jiang, M. H. (2001). J. Mater. Chem. 11, 1600-1605.]). For a related structure, see: Bak et al. (1961[Bak, B., Christensen, D., Hansen-Nygaard, L. & Rastrup-Andersen, J. (1961). J. Mol. Spectrosc. 7, 58-63.]).

[Scheme 1]

Experimental

Crystal data
  • C26H19NO

  • Mr = 361.42

  • Triclinic, [P \overline 1]

  • a = 10.1804 (6) Å

  • b = 12.0198 (7) Å

  • c = 16.0191 (10) Å

  • α = 91.752 (3)°

  • β = 101.606 (3)°

  • γ = 104.400 (3)°

  • V = 1853.07 (19) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 100 K

  • 0.38 × 0.32 × 0.18 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • 13657 measured reflections

  • 6509 independent reflections

  • 4745 reflections with I > 2σ(I)

  • Rint = 0.028

Refinement
  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 0.115

  • S = 1.08

  • 6509 reflections

  • 506 parameters

  • H-atom parameters not refined

  • Δρmax = 0.57 e Å−3

  • Δρmin = −0.27 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C61–C66 ring.

D—H⋯A D—H H⋯A DA D—H⋯A
C15—H15⋯Cg 0.93 2.97 3.787 (2) 147

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information


Comment top

The title compound, (I), has been shown to be an precursor for the production of hole transporting and/or emitting materials (Shen et al., 2005). One pot synthesis of a benzofuran derivative with a 2-substituent has been achieved by the Pd complex catalyzed Sonogashira coupling reaction of 2-iodophenol with terminal alkynes, followed by cyclization of the internal alkynes formed. The molecular structure is shown in Fig. 1. The dihedral angle between the benzofuran and benzene rings is 5.09 (8)° (C11—C16), 59.02 (8)° (C21—C26), and 67.74 (8)° (C41—C46) [18.70 (8)° (C61—C66), 52.78 (8)° (C71—C76), and 41.74 (8)° (C81—C86) for the second molecule]. There are no significant C—H···O hydrogen bonding interactions between molecules. Weak intermolecular C—H···π interactions help to stabilize the crystal structure. As shown in Fig. 1, the three phenyl rings of the amino group are arranged in a propeller-like, non-coplanar fashion. The pyramidalization of the NC3 core is weak, the N lone pair may be delocalized, mainly toward the benzofuran and increase the conjugated strength (Wang et al., 2001).

Related literature top

The title compound is a precursor for the production of hole transporting and/or emitting materials, see: Shen et al. (2005). For lone-pair delocalization, see: Wang et al. (2001). For a related structure, see: Bak et al. (1961).

Experimental top

The compound was synthesized by the following procedure. A two-necked round-bottomed flask was charged with PdCl2(PPh3)2 (100 mg), (4-ethynyl-phenyl)-diphenyl-amine (1.55 g, 5.46 mmol), CuI (30 mg), 2-iodophenol (1.00 g, 4.55 mmol), triethylamine (1.3 ml), and DMF (10 ml), and the reaction mixture stirred under nitrogen and heated at 333 K for 24 h. After cooling, the mixture was diluted with diethyl ether and the organic phase was washed with water and brine. After drying over anhydrous MgSO4 and removing the volatiles, the residue was purified by column chromatography using CH2Cl2/n-hexane as eluent, followed by recrystallization from CH2Cl2 and hexane to yield 0.60 g (37%) of (I) as a white solid. Crystals suitable for X-ray diffraction were grown from a CH2Cl2 solution layered with hexane at room temperature. 1H NMR (CDCl3): 7.69 (d, 2 H, J = 8.47 Hz), 7.54 (d, 2 H, J = 7.84 Hz), 7.32–7.24 (m, 7 H), 7.08 (tt, 7 H, J = 8.65 Hz), 6.88 (s, 1 H). FAB MS (m/e): 361.1 (M+) Anal. Calcd for C26H19NO: C, 86.40; H, 5.30; N, 3.88. Found: C, 86.54; H, 5.38; N, 3.78.

Refinement top

H atoms were located geometrically and treated as riding atoms, with C—H = 0.93 Å, and with Uiso(H) = 1.2Ueq(C).

Structure description top

The title compound, (I), has been shown to be an precursor for the production of hole transporting and/or emitting materials (Shen et al., 2005). One pot synthesis of a benzofuran derivative with a 2-substituent has been achieved by the Pd complex catalyzed Sonogashira coupling reaction of 2-iodophenol with terminal alkynes, followed by cyclization of the internal alkynes formed. The molecular structure is shown in Fig. 1. The dihedral angle between the benzofuran and benzene rings is 5.09 (8)° (C11—C16), 59.02 (8)° (C21—C26), and 67.74 (8)° (C41—C46) [18.70 (8)° (C61—C66), 52.78 (8)° (C71—C76), and 41.74 (8)° (C81—C86) for the second molecule]. There are no significant C—H···O hydrogen bonding interactions between molecules. Weak intermolecular C—H···π interactions help to stabilize the crystal structure. As shown in Fig. 1, the three phenyl rings of the amino group are arranged in a propeller-like, non-coplanar fashion. The pyramidalization of the NC3 core is weak, the N lone pair may be delocalized, mainly toward the benzofuran and increase the conjugated strength (Wang et al., 2001).

The title compound is a precursor for the production of hole transporting and/or emitting materials, see: Shen et al. (2005). For lone-pair delocalization, see: Wang et al. (2001). For a related structure, see: Bak et al. (1961).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. Molecular structure of (I) with 30% probability displacement ellipsoids, showing the atom-numbering scheme employed. H atoms are shown as small spheres of the arbitrary radii.
[4-(1-Benzofuran-2-yl)phenyl]diphenylamine top
Crystal data top
C26H19NOZ = 4
Mr = 361.42F(000) = 760
Triclinic, P1Dx = 1.295 Mg m3
Dm = 1.295 Mg m3
Dm measured by not measured
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.1804 (6) ÅCell parameters from 2733 reflections
b = 12.0198 (7) Åθ = 2.3–24.1°
c = 16.0191 (10) ŵ = 0.08 mm1
α = 91.752 (3)°T = 100 K
β = 101.606 (3)°Prism, colourless
γ = 104.400 (3)°0.38 × 0.32 × 0.18 mm
V = 1853.07 (19) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
4745 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.028
Graphite monochromatorθmax = 25.0°, θmin = 1.3°
phi and ω scansh = 1211
13657 measured reflectionsk = 1414
6509 independent reflectionsl = 019
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H-atom parameters not refined
wR(F2) = 0.115 w = 1/[σ2(Fo2) + (0.0449P)2 + 0.4753P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max < 0.001
6509 reflectionsΔρmax = 0.57 e Å3
506 parametersΔρmin = 0.27 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0038 (7)
Crystal data top
C26H19NOγ = 104.400 (3)°
Mr = 361.42V = 1853.07 (19) Å3
Triclinic, P1Z = 4
a = 10.1804 (6) ÅMo Kα radiation
b = 12.0198 (7) ŵ = 0.08 mm1
c = 16.0191 (10) ÅT = 100 K
α = 91.752 (3)°0.38 × 0.32 × 0.18 mm
β = 101.606 (3)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
4745 reflections with I > 2σ(I)
13657 measured reflectionsRint = 0.028
6509 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.115H-atom parameters not refined
S = 1.08Δρmax = 0.57 e Å3
6509 reflectionsΔρmin = 0.27 e Å3
506 parameters
Special details top

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) top
xyzUiso*/Ueq
O20.35004 (13)0.62450 (10)0.15748 (8)0.0281 (3)
O520.93820 (12)0.65312 (10)0.16480 (7)0.0255 (3)
N10.59643 (16)0.24086 (12)0.34929 (10)0.0286 (4)
N21.08301 (16)0.23701 (12)0.35939 (9)0.0266 (4)
C10.45602 (19)0.58181 (15)0.13719 (12)0.0261 (4)
C30.23645 (19)0.77012 (15)0.09996 (12)0.0283 (4)
H30.17650.76050.13750.034*
C40.2340 (2)0.84867 (16)0.03899 (12)0.0304 (5)
H40.17030.89300.03470.036*
C50.3255 (2)0.86260 (16)0.01633 (12)0.0296 (4)
H50.32200.91660.05650.036*
C60.42097 (19)0.79831 (15)0.01288 (12)0.0283 (4)
H60.48130.80830.05020.034*
C70.50337 (19)0.63539 (15)0.07242 (12)0.0278 (4)
H70.57390.62160.04800.033*
C80.42488 (19)0.71795 (15)0.04790 (12)0.0253 (4)
C90.33233 (19)0.70697 (15)0.10215 (12)0.0256 (4)
C110.49132 (19)0.49322 (15)0.19020 (12)0.0260 (4)
C120.41322 (19)0.44974 (15)0.24970 (12)0.0272 (4)
H120.33740.47740.25490.033*
C130.44657 (19)0.36651 (15)0.30096 (12)0.0274 (4)
H130.39290.33860.34020.033*
C140.55926 (19)0.32394 (15)0.29471 (12)0.0261 (4)
C150.6363 (2)0.36514 (16)0.23456 (12)0.0301 (5)
H150.71150.33670.22930.036*
C160.60269 (19)0.44760 (15)0.18251 (12)0.0289 (4)
H160.65440.47320.14190.035*
C210.58583 (19)0.25126 (15)0.43608 (12)0.0273 (4)
C220.5392 (3)0.15753 (18)0.47949 (15)0.0480 (6)
H220.51080.08390.45140.058*
C230.5342 (3)0.1722 (2)0.56531 (15)0.0544 (7)
H230.50680.10790.59460.065*
C240.5690 (2)0.2793 (2)0.60690 (14)0.0442 (6)
H240.56530.28850.66420.053*
C250.6091 (2)0.37278 (19)0.56317 (13)0.0389 (5)
H250.62810.44640.59010.047*
C260.6221 (2)0.36022 (17)0.47951 (13)0.0331 (5)
H260.65540.42500.45200.040*
C410.61579 (19)0.13819 (15)0.31304 (12)0.0262 (4)
C420.70935 (19)0.08269 (16)0.35718 (13)0.0306 (5)
H420.76210.11390.41100.037*
C430.7249 (2)0.01828 (16)0.32206 (14)0.0363 (5)
H430.78720.05500.35260.044*
C440.6488 (2)0.06517 (17)0.24196 (14)0.0372 (5)
H440.65890.13350.21860.045*
C450.5577 (2)0.00964 (16)0.19708 (13)0.0349 (5)
H450.50720.04000.14260.042*
C460.54067 (19)0.09104 (16)0.23225 (12)0.0301 (5)
H460.47820.12740.20140.036*
C510.93063 (18)0.54819 (15)0.12263 (12)0.0255 (4)
C530.8815 (2)0.82966 (17)0.11816 (13)0.0349 (5)
H530.90700.86740.17280.042*
C540.8331 (2)0.8813 (2)0.04690 (14)0.0436 (6)
H540.82580.95660.05340.052*
C550.7949 (2)0.8239 (2)0.03435 (14)0.0430 (6)
H550.76290.86170.08090.052*
C560.8034 (2)0.71253 (19)0.04757 (13)0.0359 (5)
H560.77740.67490.10220.043*
C570.87840 (19)0.54727 (16)0.03832 (12)0.0275 (4)
H570.86230.48620.00270.033*
C580.85230 (18)0.65717 (17)0.02335 (12)0.0280 (4)
C590.88955 (18)0.71878 (16)0.10309 (11)0.0264 (4)
C610.97725 (18)0.46656 (15)0.17885 (11)0.0233 (4)
C621.05605 (18)0.50525 (15)0.26096 (11)0.0241 (4)
H621.08460.58390.27750.029*
C631.09210 (18)0.42908 (15)0.31776 (11)0.0232 (4)
H631.14560.45720.37190.028*
C641.05031 (18)0.31045 (15)0.29604 (12)0.0236 (4)
C650.97473 (19)0.27131 (15)0.21315 (12)0.0271 (4)
H650.94780.19280.19620.033*
C660.93971 (19)0.34839 (16)0.15610 (12)0.0275 (4)
H660.88980.32070.10100.033*
C711.09740 (19)0.27741 (14)0.44662 (12)0.0251 (4)
C720.99253 (19)0.31705 (14)0.47079 (12)0.0250 (4)
H720.91180.31490.43060.030*
C731.0073 (2)0.35961 (15)0.55388 (12)0.0285 (4)
H730.93680.38670.56940.034*
C741.1263 (2)0.36231 (16)0.61449 (12)0.0313 (5)
H741.13580.39070.67070.038*
C751.2305 (2)0.32253 (16)0.59076 (13)0.0329 (5)
H751.31050.32380.63130.040*
C761.2171 (2)0.28082 (16)0.50731 (12)0.0299 (5)
H761.28840.25500.49180.036*
C811.11014 (18)0.12962 (15)0.34196 (12)0.0249 (4)
C821.0835 (2)0.04290 (15)0.39650 (12)0.0303 (5)
H821.04530.05530.44300.036*
C831.1128 (2)0.06090 (17)0.38260 (13)0.0385 (5)
H831.09520.11770.42000.046*
C841.1682 (2)0.08133 (17)0.31368 (14)0.0395 (5)
H841.18790.15160.30430.047*
C851.1939 (2)0.00387 (16)0.25889 (13)0.0362 (5)
H851.23040.00960.21190.043*
C861.16633 (19)0.10884 (16)0.27271 (12)0.0291 (4)
H861.18540.16580.23560.035*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O20.0275 (7)0.0278 (7)0.0355 (8)0.0112 (6)0.0160 (6)0.0056 (6)
O520.0273 (7)0.0302 (7)0.0224 (7)0.0120 (6)0.0070 (6)0.0038 (6)
N10.0355 (10)0.0227 (8)0.0310 (9)0.0108 (7)0.0111 (7)0.0013 (7)
N20.0320 (9)0.0239 (8)0.0274 (9)0.0108 (7)0.0103 (7)0.0014 (7)
C10.0243 (10)0.0240 (10)0.0322 (11)0.0068 (8)0.0106 (9)0.0002 (8)
C30.0264 (11)0.0255 (10)0.0351 (11)0.0060 (8)0.0134 (9)0.0018 (9)
C40.0279 (11)0.0266 (10)0.0369 (12)0.0093 (8)0.0053 (9)0.0016 (9)
C50.0305 (11)0.0260 (10)0.0316 (11)0.0054 (8)0.0071 (9)0.0041 (8)
C60.0276 (11)0.0297 (10)0.0280 (11)0.0056 (8)0.0092 (9)0.0017 (8)
C70.0257 (11)0.0268 (10)0.0335 (11)0.0079 (8)0.0116 (9)0.0005 (8)
C80.0225 (10)0.0226 (9)0.0299 (11)0.0035 (8)0.0071 (8)0.0033 (8)
C90.0247 (10)0.0215 (9)0.0305 (11)0.0044 (8)0.0076 (8)0.0020 (8)
C110.0265 (11)0.0222 (9)0.0303 (11)0.0053 (8)0.0099 (9)0.0003 (8)
C120.0242 (10)0.0297 (10)0.0309 (11)0.0094 (8)0.0107 (9)0.0008 (9)
C130.0280 (11)0.0272 (10)0.0280 (11)0.0061 (8)0.0100 (9)0.0013 (8)
C140.0271 (11)0.0204 (9)0.0309 (11)0.0055 (8)0.0078 (9)0.0012 (8)
C150.0278 (11)0.0292 (10)0.0396 (12)0.0125 (9)0.0151 (9)0.0039 (9)
C160.0279 (11)0.0284 (10)0.0346 (11)0.0073 (8)0.0163 (9)0.0035 (9)
C210.0257 (11)0.0275 (10)0.0324 (11)0.0102 (8)0.0106 (9)0.0033 (8)
C220.0673 (17)0.0281 (11)0.0617 (16)0.0167 (11)0.0381 (13)0.0071 (11)
C230.0773 (19)0.0516 (15)0.0594 (16)0.0356 (13)0.0452 (14)0.0292 (13)
C240.0416 (14)0.0654 (16)0.0360 (13)0.0308 (12)0.0109 (11)0.0076 (12)
C250.0254 (11)0.0519 (14)0.0347 (12)0.0041 (10)0.0047 (9)0.0080 (10)
C260.0273 (11)0.0328 (11)0.0352 (12)0.0004 (9)0.0084 (9)0.0016 (9)
C410.0236 (10)0.0219 (9)0.0339 (11)0.0050 (8)0.0099 (9)0.0005 (8)
C420.0239 (11)0.0284 (10)0.0371 (12)0.0059 (8)0.0029 (9)0.0025 (9)
C430.0268 (11)0.0299 (11)0.0551 (14)0.0120 (9)0.0098 (10)0.0010 (10)
C440.0369 (12)0.0268 (10)0.0506 (14)0.0078 (9)0.0179 (11)0.0065 (10)
C450.0356 (12)0.0323 (11)0.0330 (12)0.0028 (9)0.0076 (9)0.0056 (9)
C460.0260 (11)0.0283 (10)0.0343 (12)0.0060 (8)0.0046 (9)0.0001 (9)
C510.0211 (10)0.0282 (10)0.0287 (11)0.0049 (8)0.0108 (8)0.0016 (8)
C530.0373 (12)0.0411 (12)0.0347 (12)0.0215 (10)0.0122 (10)0.0083 (10)
C540.0504 (14)0.0519 (14)0.0431 (14)0.0330 (12)0.0173 (11)0.0182 (11)
C550.0401 (13)0.0634 (15)0.0363 (13)0.0285 (12)0.0118 (10)0.0217 (11)
C560.0261 (11)0.0575 (14)0.0265 (11)0.0134 (10)0.0080 (9)0.0078 (10)
C570.0225 (10)0.0336 (11)0.0258 (11)0.0047 (8)0.0079 (8)0.0016 (8)
C580.0186 (10)0.0427 (12)0.0251 (11)0.0088 (8)0.0089 (8)0.0065 (9)
C590.0217 (10)0.0372 (11)0.0255 (10)0.0136 (8)0.0089 (8)0.0096 (9)
C610.0201 (10)0.0270 (10)0.0254 (10)0.0069 (8)0.0100 (8)0.0028 (8)
C620.0223 (10)0.0209 (9)0.0309 (11)0.0053 (8)0.0104 (8)0.0003 (8)
C630.0196 (10)0.0258 (10)0.0249 (10)0.0060 (8)0.0069 (8)0.0000 (8)
C640.0189 (10)0.0257 (10)0.0300 (11)0.0079 (8)0.0116 (8)0.0037 (8)
C650.0281 (11)0.0226 (10)0.0318 (11)0.0059 (8)0.0108 (9)0.0034 (8)
C660.0249 (11)0.0316 (11)0.0255 (10)0.0061 (8)0.0064 (8)0.0013 (9)
C710.0295 (11)0.0201 (9)0.0276 (10)0.0067 (8)0.0102 (9)0.0021 (8)
C720.0262 (10)0.0223 (9)0.0281 (10)0.0067 (8)0.0085 (8)0.0040 (8)
C730.0307 (11)0.0236 (10)0.0340 (11)0.0077 (8)0.0128 (9)0.0016 (8)
C740.0345 (12)0.0306 (11)0.0285 (11)0.0066 (9)0.0096 (9)0.0015 (9)
C750.0282 (11)0.0362 (11)0.0327 (12)0.0083 (9)0.0032 (9)0.0004 (9)
C760.0274 (11)0.0322 (11)0.0338 (12)0.0116 (9)0.0106 (9)0.0020 (9)
C810.0208 (10)0.0228 (9)0.0316 (11)0.0066 (8)0.0061 (8)0.0016 (8)
C820.0314 (11)0.0273 (10)0.0323 (11)0.0078 (8)0.0067 (9)0.0030 (9)
C830.0486 (14)0.0260 (11)0.0401 (13)0.0138 (10)0.0023 (11)0.0044 (9)
C840.0436 (13)0.0273 (11)0.0486 (14)0.0173 (10)0.0037 (11)0.0044 (10)
C850.0355 (12)0.0333 (11)0.0417 (13)0.0118 (9)0.0108 (10)0.0077 (10)
C860.0270 (11)0.0254 (10)0.0364 (11)0.0066 (8)0.0112 (9)0.0007 (9)
Geometric parameters (Å, º) top
O2—C91.371 (2)C44—C451.375 (3)
O2—C11.393 (2)C44—H440.9300
O52—C591.375 (2)C45—C461.384 (3)
O52—C511.390 (2)C45—H450.9300
N1—C141.419 (2)C46—H460.9300
N1—C211.420 (2)C51—C571.347 (3)
N1—C411.422 (2)C51—C611.453 (2)
N2—C641.409 (2)C53—C591.373 (3)
N2—C811.417 (2)C53—C541.379 (3)
N2—C711.432 (2)C53—H530.9300
C1—C71.346 (3)C54—C551.389 (3)
C1—C111.452 (3)C54—H540.9300
C3—C91.373 (2)C55—C561.376 (3)
C3—C41.380 (3)C55—H550.9300
C3—H30.9300C56—C581.402 (3)
C4—C51.394 (3)C56—H560.9300
C4—H40.9300C57—C581.429 (3)
C5—C61.379 (3)C57—H570.9300
C5—H50.9300C58—C591.390 (3)
C6—C81.394 (3)C61—C661.392 (2)
C6—H60.9300C61—C621.394 (2)
C7—C81.439 (2)C62—C631.373 (2)
C7—H70.9300C62—H620.9300
C8—C91.391 (3)C63—C641.394 (2)
C11—C121.394 (3)C63—H630.9300
C11—C161.401 (2)C64—C651.395 (3)
C12—C131.377 (3)C65—C661.380 (3)
C12—H120.9300C65—H650.9300
C13—C141.387 (2)C66—H660.9300
C13—H130.9300C71—C761.389 (3)
C14—C151.389 (3)C71—C721.387 (2)
C15—C161.378 (3)C72—C731.377 (2)
C15—H150.9300C72—H720.9300
C16—H160.9300C73—C741.384 (3)
C21—C221.376 (3)C73—H730.9300
C21—C261.391 (3)C74—C751.379 (3)
C22—C231.393 (3)C74—H740.9300
C22—H220.9300C75—C761.382 (3)
C23—C241.361 (3)C75—H750.9300
C23—H230.9300C76—H760.9300
C24—C251.362 (3)C81—C861.389 (3)
C24—H240.9300C81—C821.391 (3)
C25—C261.380 (3)C82—C831.375 (3)
C25—H250.9300C82—H820.9300
C26—H260.9300C83—C841.378 (3)
C41—C461.386 (3)C83—H830.9300
C41—C421.388 (3)C84—C851.379 (3)
C42—C431.380 (3)C84—H840.9300
C42—H420.9300C85—C861.380 (3)
C43—C441.380 (3)C85—H850.9300
C43—H430.9300C86—H860.9300
C9—O2—C1106.04 (13)C46—C45—H45119.7
C59—O52—C51106.23 (14)C45—C46—C41120.63 (18)
C14—N1—C21118.57 (14)C45—C46—H46119.7
C14—N1—C41119.36 (15)C41—C46—H46119.7
C21—N1—C41120.84 (15)C57—C51—O52110.47 (16)
C64—N2—C81123.81 (15)C57—C51—C61135.70 (17)
C64—N2—C71117.42 (14)O52—C51—C61113.81 (15)
C81—N2—C71118.66 (14)C59—C53—C54115.53 (19)
C7—C1—O2110.70 (15)C59—C53—H53122.2
C7—C1—C11135.00 (17)C54—C53—H53122.2
O2—C1—C11114.29 (15)C53—C54—C55121.7 (2)
C9—C3—C4116.33 (17)C53—C54—H54119.1
C9—C3—H3121.8C55—C54—H54119.1
C4—C3—H3121.8C56—C55—C54121.55 (19)
C3—C4—C5121.04 (17)C56—C55—H55119.2
C3—C4—H4119.5C54—C55—H55119.2
C5—C4—H4119.5C55—C56—C58118.39 (19)
C6—C5—C4121.60 (18)C55—C56—H56120.8
C6—C5—H5119.2C58—C56—H56120.8
C4—C5—H5119.2C51—C57—C58107.57 (16)
C5—C6—C8118.39 (17)C51—C57—H57126.2
C5—C6—H6120.8C58—C57—H57126.2
C8—C6—H6120.8C59—C58—C56117.65 (18)
C1—C7—C8107.47 (16)C59—C58—C57105.66 (16)
C1—C7—H7126.3C56—C58—C57136.68 (18)
C8—C7—H7126.3C53—C59—O52124.76 (17)
C9—C8—C6118.27 (16)C53—C59—C58125.18 (17)
C9—C8—C7105.18 (16)O52—C59—C58110.05 (15)
C6—C8—C7136.55 (17)C66—C61—C62117.52 (16)
O2—C9—C3125.02 (16)C66—C61—C51122.61 (17)
O2—C9—C8110.61 (15)C62—C61—C51119.76 (16)
C3—C9—C8124.36 (17)C63—C62—C61121.01 (16)
C12—C11—C16117.99 (17)C63—C62—H62119.5
C12—C11—C1120.54 (16)C61—C62—H62119.5
C16—C11—C1121.46 (17)C62—C63—C64121.49 (17)
C13—C12—C11121.06 (17)C62—C63—H63119.3
C13—C12—H12119.5C64—C63—H63119.3
C11—C12—H12119.5C63—C64—C65117.80 (16)
C12—C13—C14120.69 (17)C63—C64—N2118.39 (16)
C12—C13—H13119.7C65—C64—N2123.79 (16)
C14—C13—H13119.7C66—C65—C64120.41 (17)
C13—C14—C15118.72 (17)C66—C65—H65119.8
C13—C14—N1120.79 (17)C64—C65—H65119.8
C15—C14—N1120.48 (16)C65—C66—C61121.71 (17)
C16—C15—C14120.88 (17)C65—C66—H66119.1
C16—C15—H15119.6C61—C66—H66119.1
C14—C15—H15119.6C76—C71—C72119.18 (17)
C15—C16—C11120.61 (17)C76—C71—N2120.89 (16)
C15—C16—H16119.7C72—C71—N2119.90 (16)
C11—C16—H16119.7C73—C72—C71120.38 (17)
C22—C21—C26117.98 (18)C73—C72—H72119.8
C22—C21—N1122.68 (17)C71—C72—H72119.8
C26—C21—N1119.34 (17)C72—C73—C74120.42 (18)
C21—C22—C23120.4 (2)C72—C73—H73119.8
C21—C22—H22119.8C74—C73—H73119.8
C23—C22—H22119.8C75—C74—C73119.36 (18)
C24—C23—C22121.0 (2)C75—C74—H74120.3
C24—C23—H23119.5C73—C74—H74120.3
C22—C23—H23119.5C74—C75—C76120.56 (18)
C23—C24—C25118.8 (2)C74—C75—H75119.7
C23—C24—H24120.6C76—C75—H75119.7
C25—C24—H24120.6C75—C76—C71120.09 (17)
C24—C25—C26121.2 (2)C75—C76—H76120.0
C24—C25—H25119.4C71—C76—H76120.0
C26—C25—H25119.4C86—C81—C82118.53 (16)
C25—C26—C21120.42 (19)C86—C81—N2121.87 (16)
C25—C26—H26119.8C82—C81—N2119.58 (16)
C21—C26—H26119.8C83—C82—C81120.81 (19)
C46—C41—C42118.41 (17)C83—C82—H82119.6
C46—C41—N1120.36 (16)C81—C82—H82119.6
C42—C41—N1121.24 (17)C82—C83—C84120.50 (19)
C43—C42—C41120.65 (18)C82—C83—H83119.8
C43—C42—H42119.7C84—C83—H83119.8
C41—C42—H42119.7C85—C84—C83119.06 (18)
C44—C43—C42120.54 (19)C85—C84—H84120.5
C44—C43—H43119.7C83—C84—H84120.5
C42—C43—H43119.7C84—C85—C86120.97 (19)
C45—C44—C43119.21 (18)C84—C85—H85119.5
C45—C44—H44120.4C86—C85—H85119.5
C43—C44—H44120.4C85—C86—C81120.13 (18)
C44—C45—C46120.54 (19)C85—C86—H86119.9
C44—C45—H45119.7C81—C86—H86119.9
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C61–C66 ring.
D—H···AD—HH···AD···AD—H···A
C15—H15···Cg0.932.973.787 (2)147

Experimental details

Crystal data
Chemical formulaC26H19NO
Mr361.42
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)10.1804 (6), 12.0198 (7), 16.0191 (10)
α, β, γ (°)91.752 (3), 101.606 (3), 104.400 (3)
V3)1853.07 (19)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.38 × 0.32 × 0.18
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
13657, 6509, 4745
Rint0.028
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.115, 1.08
No. of reflections6509
No. of parameters506
H-atom treatmentH-atom parameters not refined
Δρmax, Δρmin (e Å3)0.57, 0.27

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C61–C66 ring.
D—H···AD—HH···AD···AD—H···A
C15—H15···Cg0.932.973.787 (2)147
 

Acknowledgements

This work was partially supported by the Institute of Chemistry, Academia Sinica, and Cardinal Tien College of Healthcare & Management.

References

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First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
First citationFarrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.  CrossRef CAS IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationShen, J. Y., Lee, C. Y., Huang, T.-H., Lin, J. T., Tao, Y.-T., Chien, C.-H. & Tsai, C. (2005). J. Mater. Chem. 15, 2455–2463.  Web of Science CrossRef CAS Google Scholar
First citationWang, X. M., Wang, D., Zhou, G. Y., Yu, W. T., Zhou, Y. F., Fang, Q. & Jiang, M. H. (2001). J. Mater. Chem. 11, 1600–1605.  Web of Science CSD CrossRef CAS Google Scholar

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