organic papers
o2440
Yanget al. C27H25N2P doi:10.1107/S160053680601871X Acta Cryst.(2006). E62, o2440–o2441
Acta Crystallographica Section E Structure Reports
Online
ISSN 1600-5368
4-[2-(Diphenylphosphino)phenyliminomethyl]-N
,
N
-dimethylaniline, a new Schiff base
containing triphenylphosphine
Kai-Bin Yang, Li-Rong Lin and Rong-Bin Huang*
Department of Chemistry, Xiamen University, Xiamen 361005, People’s Republic of China
Correspondence e-mail: rbhuang@xmu.edu.cn
Key indicators
Single-crystal X-ray study T= 173 K
Mean(C–C) = 0.003 A˚ Rfactor = 0.056 wRfactor = 0.141
Data-to-parameter ratio = 17.4
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
Received 10 May 2006 Accepted 19 May 2006
#2006 International Union of Crystallography All rights reserved
The title compound, C27H25N2P, is a Schiff base containing triphenylphosphine. The molecule has a trans configuration about the C N double bond [1.277 (2) A˚ ]. The crystal packing is stabilized by van der Waals forces.
Comment
Schiff base ligands have various applications in the fields of synthesis and catalysis, and exhibit biological activity (Cozziet al., 2003; Qiaoet al., 2004; Maciejewskaet al., 1999; Jalilet al., 2001; Li et al., 2005). Some Schiff bases containing oxygen, sulfur and complexes of transition metal ions have been synthesized (Riveraet al., 2006; Sahet al., 2006; Sharif et al., 2006) but few Schiff bases containing phosphorus have been reported. A Schiff base containing triphenylphosphine may be expected to be a useful bidentate ligand with new properties, because triphenylphosphine is a well known ligand for coordination compounds. Here we present the title compound, (I), a new Schiff base derivative containing triphenlphosphine.
In (I) (Fig. 1), all bond lengths and angles show normal values. The molecule has a trans configuration about the C9 N2 double bond. The crystal packing is stabilized by van der Waals forces.
Experimental
2-(Diphenylphosphino)benzenamine was prepared according to the literature method of Papathanasiouet al.(1997). The Schiff base was synthesized by refluxing an ethanol solution (20 ml) of
4-(dimethyl-amino)benzaldehyde (10 mmol) and
Crystal data
C27H25N2P
Mr= 408.46
Monoclinic,P21=c
a= 17.579 (4) A˚
b= 14.419 (3) A˚
c= 8.732 (2) A˚
= 100.985 (4)
V= 2172.7 (8) A˚3
Z= 4
Dx= 1.249 Mg m 3
MoKradiation
= 0.14 mm 1
T= 173 (2) K Block, yellow 0.500.430.21 mm
Data collection
Bruker SMART APEX 2000 CCD diffractometer
!scans
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)
Tmin= 0.932,Tmax= 0.971
12521 measured reflections 4719 independent reflections 4172 reflections withI> 2(I)
Rint= 0.024
max= 27.0
Refinement
Refinement onF2
R[F2> 2(F2)] = 0.056
wR(F2) = 0.141
S= 1.11 4719 reflections 271 parameters
H-atom parameters constrained
w= 1/[2(F
o2) + (0.0695P)2 + 0.8283P]
whereP= (Fo2+ 2Fc2)/3 (/)max< 0.001
max= 0.57 e A˚ 3
min= 0.42 e A˚ 3
All H atoms were positioned geometrically, with C—H distances of 0.95–0.98 A˚ , and refined using a riding model, withUiso(H) = 1.2 or
1.5Ueq(C).
Data collection:SMART(Bruker, 2001); cell refinement:SAINT
(Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97(Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics:
ORTEPII (Johnson, 1976); software used to prepare material for publication:SHELXL97.
References
Bruker (2001).SAINTandSMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Cozzi, P. G., Dolci, L. S., Garelli, A., Montalti, M., Prodi, L. & Zaccheroni, N. (2003).New J. Chem.27, 692–697.
Jalil, M. A., Fujinami, S. & Nishikawa, H. (2001).J. Chem. Soc. Dalton Trans.
pp. 1091–1098.
Johnson, C. K. (1976).ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.
Li, L.-Z., Zhao, C., Xu, T., Ji, H.-W., Yu, Y.-H., Guo, G.-Q. & Chao, H. (2005).
J. Inorg. Biochem.99, 1076–1082.
Maciejewska, D., Pawlak, D. & Koleva, V. (1999).J. Phys. Org. Chem.12, 875– 880.
Papathanasiou, P., Salem, G., Waring, P. & Willis, A. C. (1997).J. Chem. Soc. Dalton Trans.pp. 3435–3443.
Qiao, J., Wang, L.-D., Duan, L., Li, Y., Zhang, D.-Q. & Qiu, Y. (2004).Inorg. Chem.43, 5096–5102.
Rivera, J. M., Reyes, H., Cortes, A. & Santillan, R. (2006).Chem. Mater.18, 1174–1183.
Sah, A. K., Tanase, T. & Mikuriya, M. (2006).Inorg. Chem.45, 2083–2092. Sharif, S., Denisov, G. S., Toney, M. D. & Limbach, H. (2006).J. Am. Chem.
Soc.128, 3375–3387.
Sheldrick, G. M. (1996).SADABS. University of Go¨ttingen, Germany. Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of
[image:2.610.316.565.71.228.2]Go¨ttingen, Germany. Figure 1
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sup-1 Acta Cryst. (2006). E62, o2440–o2441
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Acta Cryst. (2006). E62, o2440–o2441 [https://doi.org/10.1107/S160053680601871X]
4-[2-(Diphenylphosphino)phenyliminomethyl]-N,N-dimethylaniline, a new
Schiff base containing triphenylphosphine
Kai-Bin Yang, Li-Rong Lin and Rong-Bin Huang
4-[2-(Diphenylphosphino)phenyliminomethyl]-N,N-dimethylaniline
Crystal data
C27H25N2P
Mr = 408.46
Monoclinic, P21/c
Hall symbol: -P 2ybc
a = 17.579 (4) Å
b = 14.419 (3) Å
c = 8.732 (2) Å
β = 100.985 (4)°
V = 2172.7 (8) Å3
Z = 4
F(000) = 864
Dx = 1.249 Mg m−3
Mo Kα radiation, λ = 0.71073 Å Cell parameters from 5143 reflections
θ = 2.4–28.3°
µ = 0.14 mm−1
T = 173 K Block, yellow
0.50 × 0.43 × 0.21 mm
Data collection
Bruker SMART APEX 2000 CCD diffractometer
Radiation source: fine-focus sealed tube Graphite monochromator
ω scans
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)
Tmin = 0.932, Tmax = 0.971
12521 measured reflections 4719 independent reflections 4172 reflections with I > 2σ(I)
Rint = 0.024
θmax = 27.0°, θmin = 1.8°
h = −18→22
k = −15→18
l = −11→10
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.056
wR(F2) = 0.141
S = 1.11 4719 reflections 271 parameters 0 restraints
Primary atom site location: structure-invariant direct methods
Secondary atom site location: difference Fourier map
Hydrogen site location: inferred from neighbouring sites
H-atom parameters constrained
w = 1/[σ2(F
o2) + (0.0695P)2 + 0.8283P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max < 0.001
Δρmax = 0.57 e Å−3
Δρmin = −0.42 e Å−3
Special details
Experimental. Elemental analysis found: C 79.40; H 6.19; N 6.85%; calculated for C27H25N2P: C 79.39; H 6.17; N 6.86;
P 7.58%. MS: M+/Z, 408. Spectroscopic analysis: 1H NMR (DMSO-d
6, p.p.m.) 8.195(CH), 7.698–7.497(ArH),7.395–
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 > 2σ(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)
x y z Uiso*/Ueq
supporting information
sup-3 Acta Cryst. (2006). E62, o2440–o2441
C18 0.37715 (17) 0.70615 (15) 0.3252 (3) 0.0549 (7) H18A 0.3589 0.7474 0.2415 0.066* C19 0.45444 (18) 0.68644 (17) 0.3650 (3) 0.0593 (7) H19A 0.4899 0.7135 0.3084 0.071* C20 0.48064 (15) 0.62753 (16) 0.4868 (3) 0.0514 (6) H20A 0.5345 0.6154 0.5167 0.062* C21 0.42884 (12) 0.58548 (14) 0.5666 (2) 0.0382 (5) H21A 0.4476 0.5440 0.6498 0.046* C22 0.33259 (10) 0.48142 (12) 0.7738 (2) 0.0284 (4) C23 0.34387 (12) 0.38636 (14) 0.7739 (2) 0.0374 (4) H23A 0.3218 0.3507 0.6850 0.045* C24 0.38727 (13) 0.34310 (15) 0.9034 (3) 0.0452 (5) H24A 0.3945 0.2778 0.9030 0.054* C25 0.41996 (13) 0.39410 (16) 1.0329 (3) 0.0446 (5) H25A 0.4501 0.3641 1.1208 0.054* C26 0.40883 (12) 0.48808 (16) 1.0345 (2) 0.0400 (5) H26A 0.4313 0.5234 1.1236 0.048* C27 0.36496 (11) 0.53156 (14) 0.9067 (2) 0.0345 (4) H27A 0.3567 0.5966 0.9094 0.041*
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
C23 0.0388 (11) 0.0353 (10) 0.0355 (11) 0.0013 (8) 0.0006 (8) 0.0005 (8) C24 0.0472 (12) 0.0378 (11) 0.0473 (12) 0.0056 (9) 0.0010 (10) 0.0090 (9) C25 0.0394 (11) 0.0562 (13) 0.0346 (11) 0.0020 (10) −0.0020 (9) 0.0114 (9) C26 0.0359 (10) 0.0536 (12) 0.0282 (10) −0.0058 (9) 0.0002 (8) 0.0003 (9) C27 0.0331 (10) 0.0381 (10) 0.0318 (10) −0.0044 (8) 0.0049 (8) −0.0008 (8)
Geometric parameters (Å, º)
P1—C22 1.828 (2) C11—H11A 0.9500
P1—C15 1.833 (2) C12—C13 1.371 (3)
P1—C16 1.834 (2) C12—H12A 0.9500
N1—C3 1.360 (3) C13—C14 1.388 (3)
N1—C1 1.432 (3) C13—H13A 0.9500
N1—C2 1.447 (3) C14—C15 1.390 (3)
N2—C9 1.277 (2) C14—H14A 0.9500
N2—C10 1.410 (2) C16—C21 1.377 (3)
C1—H1O 0.9800 C16—C17 1.391 (3)
C1—H1N 0.9800 C17—C18 1.384 (3)
C1—H1M 0.9800 C17—H17A 0.9500
C2—H2Z 0.9800 C18—C19 1.367 (4)
C2—H2Y 0.9800 C18—H18A 0.9500
C2—H2X 0.9800 C19—C20 1.370 (4)
C3—C4 1.404 (3) C19—H19A 0.9500
C3—C8 1.409 (3) C20—C21 1.387 (3)
C4—C5 1.371 (3) C20—H20A 0.9500
C4—H4A 0.9500 C21—H21A 0.9500
C5—C6 1.388 (3) C22—C23 1.385 (3)
C5—H5A 0.9500 C22—C27 1.393 (3)
C6—C7 1.396 (3) C23—C24 1.386 (3)
C6—C9 1.445 (3) C23—H23A 0.9500
C7—C8 1.368 (3) C24—C25 1.379 (3)
C7—H7A 0.9500 C24—H24A 0.9500
C8—H8A 0.9500 C25—C26 1.370 (3)
C9—H9A 0.9500 C25—H25A 0.9500
C10—C11 1.396 (3) C26—C27 1.380 (3)
C10—C15 1.400 (2) C26—H26A 0.9500
C11—C12 1.374 (3) C27—H27A 0.9500
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sup-5 Acta Cryst. (2006). E62, o2440–o2441
