(IUCr) (3-Aminophenyl)diphenylphosphine oxide-2-propanol (1/1)

Volume 64
Part 3
Pages o614-o615
March 2008

Received 10 February 2008
Accepted 17 February 2008
Online 22 February 2008

Key indicators
Single-crystal X-ray study
T = 120 K
Mean (C-C) = 0.004 Å
Disorder in main residue
R = 0.062
wR = 0.122
Data-to-parameter ratio = 20.3
Details

(3-Aminophenyl)diphenylphosphine oxide-2-propanol (1/1)

Hossein Mahdavi,^a ^* Javad Amani ^a and Jafar Attar Gharamaleki ^b

^aSchool of Chemistry, University College of Science, University of Tehran, PO Box 14155-645, Tehran, Iran, and ^bFaculty of Chemistry, Tarbiat Moallem University, Tehran, Iran
Correspondence e-mail: hmahdavi@khayam.ut.ac.ir

The title compound, C₁₈H₁₆NOP·C₃H₈O, was synthesized by the reduction of (3-nitrophenyl)diphenylphosphine oxide in the presence of 2-propanol as recrystallization solvent. There are two molecules in the asymmetric unit. Each P atom is tetracoordinated by three C and one O atom from two phenyl fragments, one aniline group and one double-bonded O atom in a distorted tetrahedral geometry. C-H [pi] and N-H [pi] interactions are present. In the crystal structure, a wide range of non-covalent interactions consisting of hydrogen bonding [of the types of O-HO, N-HO and C-HO, with DA distances ranging from 2.680 (3) to 3.478 (3) Å] and [pi] - [pi] [centroid-centroid distance of 3.7720 (15) Å] stacking interactions connect the various components into a supramolecular structure.

Related literature

For related literature, see: Aghabozorg et al. (2007); Aghabozorg et al. (2008); Al-Farhan (1992); Chael & Buchmeiser (2003); Mahdavi & Amani (2008).

Experimental

Crystal data

C₁₈H₁₆NOP·C₃H₈O
M_r = 353.38
Triclinic, $[P \overline 1]$
a = 9.0077 (9) Å
b = 11.7682 (12) Å
c = 18.7580 (18) Å
= 78.717 (3)°
= 79.169 (3)°
= 86.216 (2)°
V = 1914.4 (3) Å³
Z = 4
Mo K radiation
= 0.16 mm^-1
T = 120 (2) K
0.35 × 0.18 × 0.12 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: none
18065 measured reflections
9090 independent reflections
6687 reflections with I > 2(I)
R_int = 0.022

Refinement

R[F² > 2(F²)] = 0.061
wR(F²) = 0.121
S = 1.03
9090 reflections
447 parameters
1 restraint
H-atom parameters constrained
_max = 1.04 e Å^-3
_min = -0.71 e Å^-3

Table 1
Selected geometric parameters (Å, °)

P1-O1	1.4974 (16)
P1-C7	1.799 (2)
P1-C13	1.802 (2)
P1-C1	1.803 (2)
P1'-O1'	1.4959 (16)
P1'-C1'	1.792 (2)
P1'-C7'	1.803 (2)
P1'-C13'	1.803 (2)

O1-P1-C7	112.51 (10)
O1-P1-C13	112.56 (10)
C7-P1-C13	105.87 (10)
O1-P1-C1	112.47 (10)
C7-P1-C1	106.71 (10)
C13-P1-C1	106.21 (10)
O1'-P1'-C1'	112.49 (10)
O1'-P1'-C7'	111.81 (10)
C1'-P1'-C7'	106.37 (11)
O1'-P1'-C13'	110.02 (10)
C1'-P1'-C13'	108.52 (11)
C7'-P1'-C13'	107.41 (10)

Table 2
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1AO1ⁱ	0.88	2.11	2.982 (3)	172
N1-H1BO2Sⁱⁱ	0.88	2.19	3.051 (3)	165
O1S-H1SO1'	0.84	1.84	2.680 (3)	179
O2S-H2SO1	0.84	1.95	2.770 (3)	167
N1A-H1'AO1'ⁱⁱⁱ	0.88	2.16	2.970 (3)	154
N1A-H1'BO1Sⁱⁱ	0.88	2.10	2.975 (3)	173
N1B-H1'CO2S^iv	0.88	2.10	2.869 (3)	146
C9-H9O1S^v	0.95	2.56	3.288 (3)	134
C14-H14O2S	0.95	2.56	3.478 (3)	163
C3S-H3SCCg1ⁱⁱⁱ	0.98	2.84	3.741 (4)	153
C4S-H4SCCg2ⁱ	0.98	2.93	3.645 (3)	131
N1B-H1'DCg3^iv	0.98	2.45	3.296 (8)	161
Symmetry codes: (i) -x+2, -y+1, -z; (ii) x+1, y, z; (iii) -x+1, -y, -z+1; (iv) -x+1, -y+1, -z+1; (v) -x+1, -y+1, -z. Cg1, Cg2 and Cg3 are the centroids of atoms C13'-C18', C7-C12 and C7'-C12', respectively.

Data collection: SMART (Bruker, 2007); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: OM2214 ).

Acknowledgements

We are grateful to the Research Council of the University of Tehran.

References

Aghabozorg, H., Attar Gharamaleki, J., Daneshvar, S., Ghadermazi, M. & Khavasi, H. R. (2008). Acta Cryst. E64, m187-m188.
Aghabozorg, H., Attar Gharamaleki, J., Motyeian, E. & Ghadermazi, M. (2007). Acta Cryst. E63, m2793-m2794.
Al-Farhan, K. A. (1992). J. Cryst. Spect. Res., 22(6), 687-689.
Bruker (2007). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.
Chael, M. & Buchmeiser, R. (2003). In Polymeric Materials in Organic Synthesis and Catalysis. New York: Wiley.
Mahdavi, H. & Amani, J. (2008). Tetrahedron Lett. In the press.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds