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

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ISSN: 2056-9890

4-Di­phenyl­phosphanyl-1,5-naphthyridine

aDepartment of Applied Chemistry, Nanjing College of Chemical Technology, No. 625 Geguan Road, Dachang, Nanjing 210048, People's Republic of China
*Correspondence e-mail: adsony05@163.com

(Received 4 September 2012; accepted 20 September 2012; online 26 September 2012)

The asymmetric unit of the title compound, C20H15N2P, contains two independent mol­ecules with similar structures. The 1,5-naphthyridine ring system is nearly planar, with maximum deviations of 0.010 (3) and 0.012 (3) Å; its mean plane is oriented with respect to the two phenyl rings at 79.69 (12) and 84.00 (10)° in one mol­ecule, and at 74.25 (12) and 82.05 (11)° in the other. The two phenyl rings are twisted with respect to each other with a dihedral angle of 75.96 (14)° in one mol­ecule and 86.30 (13)° in the other.

Related literature

For applications of the title compound, see: Badawneh et al. (2001[Badawneh, M., Ferrarini, P. L., Calderone, V., Manera, C., Martinotti, E., Mori, C., Saccomanni, G. & Testai, L. (2001). Eur. J. Med. Chem. 36, 925-934.]); Hawes et al. (1977[Hawes, E. M., Gorecki, D. K. J. & Gedir, G. G. (1977). J. Med. Chem. 20, 838-841.]); Goswami & Mukherjee (1997[Goswami, S. & Mukherjee, R. (1997). Tetrahedron Lett. 38, 1619-1621.]); Goswami et al. (2001[Goswami, S., Ghosh, K. & Mukherjee, R. (2001). Tetrahedron, 57, 4987-4993.], 2005[Goswami, S., Mukherjee, R., Mukherjee, S., Jana, S., Maity, A. C. & Adak, A. K. (2005). Molecules, 10, 929-934.]). For the synthesis of the title compound, see: Chen et al. (2012[Chen, C., Wang, K.-Y., Jiang, P., Song, G.-L. & Zhu, H.-J. (2012). Inorg. Chem. Commun. 17, 116-119.]).

[Scheme 1]

Experimental

Crystal data
  • C20H15N2P

  • Mr = 314.31

  • Triclinic, [P \overline 1]

  • a = 10.1103 (7) Å

  • b = 11.7020 (8) Å

  • c = 15.7060 (11) Å

  • α = 71.54 (3)°

  • β = 75.05 (3)°

  • γ = 71.37 (3)°

  • V = 1644.6 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.17 mm−1

  • T = 293 K

  • 0.30 × 0.20 × 0.20 mm

Data collection
  • Enraf–Nonius CAD-4 diffractometer

  • Absorption correction: ψ scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.952, Tmax = 0.967

  • 6393 measured reflections

  • 6024 independent reflections

  • 4473 reflections with I > 2σ(I)

  • Rint = 0.019

  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement
  • R[F2 > 2σ(F2)] = 0.047

  • wR(F2) = 0.151

  • S = 1.00

  • 6024 reflections

  • 416 parameters

  • H-atom parameters constrained

  • Δρmax = 0.24 e Å−3

  • Δρmin = −0.18 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994[Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

The title compound, (I), is an important intermediate in medicine (Badawneh et al., 2001; Hawes et al., 1977). Naphthyridines are also used as a key molecule in molecular recognition chemistry (Goswami & Mukherjee, 1997; Goswami et al., 2005, 2001).

The molecular structure of (I) is shown in Fig. 1. The asymmetric unit of the title compound, C20H15N2P, contains two independent molecules with the similar structure. The 1,5-naphthrydine ring system is nearly planar with the maximum deviation of 0.010 (3) and 0.012 (3) Å, respectively; its mean plane is oriented with respect to the two phenyl rings at 79.69 (12) and 84.00 (10)° in one molecule and 74.25 (12) and 82.05 (11)° in the other. The two phenyl rings are twisted to each other with a dihedral angle of 75.96 (14)° in one molecule and 86.30 (13)° in the other.

The crystal packing of the molecules in the crystal is influenced by van der Waals forces.

Related literature top

For applications of the title compound, see: Badawneh et al. (2001); Hawes et al. (1977); Goswami & Mukherjee (1997); Goswami et al. (2001, 2005). For the synthesis of the title compound, see: Chen et al. (2012).

Experimental top

The title compound was synthesized according to the published procedure (Chen et al., 2012). Crystals suitable for X-ray analysis were obtained by dissolving it(0.5 g) in tetrahydrofuran (20 ml) and evaporating the solvent slowly at room temperature for about 5 d.

Refinement top

H atoms were positioned geometrically, with C—H = 0.93 Å for aromatic, and constrained to ride on their parent atoms, with Uĩso~(H) = xU~eq~(C), where x = 1.2 for aromatic H,and x = 1.5 for other H.

Structure description top

The title compound, (I), is an important intermediate in medicine (Badawneh et al., 2001; Hawes et al., 1977). Naphthyridines are also used as a key molecule in molecular recognition chemistry (Goswami & Mukherjee, 1997; Goswami et al., 2005, 2001).

The molecular structure of (I) is shown in Fig. 1. The asymmetric unit of the title compound, C20H15N2P, contains two independent molecules with the similar structure. The 1,5-naphthrydine ring system is nearly planar with the maximum deviation of 0.010 (3) and 0.012 (3) Å, respectively; its mean plane is oriented with respect to the two phenyl rings at 79.69 (12) and 84.00 (10)° in one molecule and 74.25 (12) and 82.05 (11)° in the other. The two phenyl rings are twisted to each other with a dihedral angle of 75.96 (14)° in one molecule and 86.30 (13)° in the other.

The crystal packing of the molecules in the crystal is influenced by van der Waals forces.

For applications of the title compound, see: Badawneh et al. (2001); Hawes et al. (1977); Goswami & Mukherjee (1997); Goswami et al. (2001, 2005). For the synthesis of the title compound, see: Chen et al. (2012).

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. A packing diagram of (I).
4-Diphenylphosphanyl-1,5-naphthyridine top
Crystal data top
C20H15N2PZ = 4
Mr = 314.31F(000) = 656
Triclinic, P1Dx = 1.269 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.1103 (7) ÅCell parameters from 25 reflections
b = 11.7020 (8) Åθ = 10–14°
c = 15.7060 (11) ŵ = 0.17 mm1
α = 71.54 (3)°T = 293 K
β = 75.05 (3)°Block, yellow
γ = 71.37 (3)°0.30 × 0.20 × 0.20 mm
V = 1644.6 (4) Å3
Data collection top
Enraf–Nonius CAD-4
diffractometer
4473 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.019
Graphite monochromatorθmax = 25.4°, θmin = 1.4°
ω/2θ scansh = 012
Absorption correction: ψ scan
(North et al., 1968)
k = 1314
Tmin = 0.952, Tmax = 0.967l = 1818
6393 measured reflections3 standard reflections every 200 reflections
6024 independent reflections intensity decay: 1%
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)] = 0.047H-atom parameters constrained
wR(F2) = 0.151 w = 1/[σ2(Fo2) + (0.1P)2 + 0.1P]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
6024 reflectionsΔρmax = 0.24 e Å3
416 parametersΔρmin = 0.18 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: 0.056 (4)
Crystal data top
C20H15N2Pγ = 71.37 (3)°
Mr = 314.31V = 1644.6 (4) Å3
Triclinic, P1Z = 4
a = 10.1103 (7) ÅMo Kα radiation
b = 11.7020 (8) ŵ = 0.17 mm1
c = 15.7060 (11) ÅT = 293 K
α = 71.54 (3)°0.30 × 0.20 × 0.20 mm
β = 75.05 (3)°
Data collection top
Enraf–Nonius CAD-4
diffractometer
4473 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.019
Tmin = 0.952, Tmax = 0.9673 standard reflections every 200 reflections
6393 measured reflections intensity decay: 1%
6024 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.151H-atom parameters constrained
S = 1.00Δρmax = 0.24 e Å3
6024 reflectionsΔρmin = 0.18 e Å3
416 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
P10.66814 (7)0.57637 (5)0.05824 (4)0.0532 (2)
N10.4162 (3)0.9483 (2)0.11519 (15)0.0820 (7)
C10.3612 (3)0.8979 (3)0.0324 (2)0.0875 (10)
H1B0.27000.93870.00930.105*
N20.7623 (2)0.71544 (18)0.12779 (13)0.0590 (5)
C20.4291 (3)0.7868 (3)0.02464 (17)0.0673 (7)
H2B0.38210.75590.08270.081*
C30.5643 (2)0.7238 (2)0.00517 (14)0.0504 (5)
C40.6276 (2)0.7760 (2)0.09501 (15)0.0499 (5)
C50.8181 (3)0.7656 (3)0.21080 (18)0.0682 (7)
H5A0.91000.72580.23350.082*
C60.7487 (3)0.8749 (3)0.26760 (19)0.0747 (8)
H6A0.79340.90610.32630.090*
C70.6156 (3)0.9346 (3)0.23573 (18)0.0760 (8)
H7A0.56761.00730.27260.091*
C80.5500 (3)0.8869 (2)0.14705 (16)0.0604 (6)
C90.5452 (3)0.5467 (2)0.16628 (16)0.0530 (6)
C100.5550 (3)0.5700 (2)0.24469 (16)0.0638 (7)
H10A0.62290.60920.24290.077*
C110.4666 (3)0.5367 (3)0.32552 (19)0.0778 (8)
H11A0.47640.55210.37780.093*
C120.3649 (3)0.4813 (3)0.3295 (2)0.0857 (9)
H12A0.30450.45990.38430.103*
C130.3518 (4)0.4573 (3)0.2530 (3)0.0998 (11)
H13A0.28260.41920.25540.120*
C140.4404 (4)0.4896 (3)0.1730 (2)0.0858 (9)
H14A0.43040.47280.12120.103*
C150.7959 (2)0.6320 (2)0.08854 (14)0.0490 (5)
C160.9299 (3)0.5519 (2)0.09739 (16)0.0586 (6)
H16A0.95160.47290.08800.070*
C171.0306 (3)0.5877 (3)0.11983 (18)0.0705 (7)
H17A1.12050.53390.12390.085*
C180.9986 (3)0.7034 (3)0.13635 (18)0.0706 (7)
H18A1.06630.72710.15250.085*
C190.8658 (3)0.7839 (2)0.12884 (16)0.0613 (6)
H19A0.84390.86180.14030.074*
C200.7658 (3)0.7491 (2)0.10448 (15)0.0533 (6)
H20A0.67710.80430.09860.064*
P20.87225 (6)0.89905 (5)0.46590 (4)0.04682 (19)
N30.8062 (2)1.09211 (19)0.29639 (13)0.0635 (5)
N41.1480 (3)0.9364 (2)0.17523 (15)0.0769 (7)
C210.8431 (4)1.2010 (3)0.1386 (2)0.0902 (10)
H21A0.80801.26760.09200.108*
C220.7647 (4)1.1837 (3)0.2274 (2)0.0790 (8)
H22A0.67791.24090.23780.095*
C230.9337 (3)1.0089 (2)0.27942 (15)0.0533 (6)
C240.9814 (2)0.9077 (2)0.35274 (15)0.0500 (5)
C251.1114 (3)0.8266 (2)0.33337 (17)0.0612 (6)
H25A1.14750.75900.37910.073*
C261.1890 (3)0.8465 (3)0.24434 (19)0.0763 (8)
H26A1.27690.79070.23400.092*
C271.0201 (3)1.0188 (3)0.19230 (16)0.0646 (7)
C280.9701 (4)1.1202 (3)0.12131 (19)0.0832 (9)
H28A1.02401.13150.06300.100*
C290.7225 (2)0.85058 (19)0.45554 (14)0.0471 (5)
C300.6058 (3)0.8561 (2)0.52547 (16)0.0610 (6)
H30A0.60700.88300.57490.073*
C310.4878 (3)0.8223 (3)0.5231 (2)0.0713 (7)
H31A0.41110.82600.57080.086*
C320.4836 (3)0.7835 (3)0.4509 (2)0.0721 (7)
H32A0.40410.76130.44900.087*
C330.5972 (3)0.7775 (3)0.3813 (2)0.0725 (7)
H33A0.59440.75090.33200.087*
C340.7168 (3)0.8104 (2)0.38273 (16)0.0581 (6)
H34A0.79320.80560.33480.070*
C350.9758 (2)0.7539 (2)0.53228 (14)0.0457 (5)
C361.0835 (3)0.7605 (2)0.56829 (17)0.0596 (6)
H36A1.10330.83690.55660.072*
C371.1621 (3)0.6555 (3)0.62125 (19)0.0711 (7)
H37A1.23590.66110.64370.085*
C381.1314 (3)0.5431 (3)0.64080 (19)0.0710 (7)
H38A1.18330.47250.67730.085*
C391.0240 (3)0.5347 (2)0.6064 (2)0.0745 (8)
H39A1.00290.45840.62000.089*
C400.9475 (3)0.6386 (2)0.55198 (17)0.0614 (6)
H40A0.87610.63180.52810.074*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0635 (4)0.0426 (3)0.0511 (4)0.0040 (3)0.0171 (3)0.0128 (3)
N10.0852 (17)0.0746 (15)0.0546 (13)0.0178 (13)0.0169 (12)0.0088 (11)
C10.0704 (18)0.090 (2)0.0652 (18)0.0263 (16)0.0094 (14)0.0193 (16)
N20.0597 (12)0.0575 (12)0.0549 (12)0.0071 (10)0.0067 (9)0.0187 (10)
C20.0653 (16)0.0725 (16)0.0443 (13)0.0034 (13)0.0069 (11)0.0116 (12)
C30.0597 (14)0.0474 (12)0.0426 (12)0.0036 (10)0.0150 (10)0.0149 (10)
C40.0605 (14)0.0460 (12)0.0444 (12)0.0068 (10)0.0135 (10)0.0167 (10)
C50.0675 (16)0.0739 (17)0.0613 (16)0.0179 (14)0.0010 (13)0.0250 (14)
C60.095 (2)0.0746 (18)0.0524 (15)0.0277 (16)0.0019 (14)0.0165 (14)
C70.101 (2)0.0638 (16)0.0503 (15)0.0100 (16)0.0188 (15)0.0035 (13)
C80.0704 (16)0.0541 (14)0.0494 (13)0.0017 (12)0.0138 (12)0.0155 (11)
C90.0602 (14)0.0435 (12)0.0547 (13)0.0128 (10)0.0205 (11)0.0043 (10)
C100.0676 (16)0.0775 (17)0.0527 (14)0.0356 (14)0.0129 (12)0.0065 (12)
C110.0804 (19)0.100 (2)0.0571 (16)0.0427 (17)0.0135 (14)0.0053 (15)
C120.083 (2)0.094 (2)0.0741 (19)0.0470 (18)0.0125 (16)0.0091 (17)
C130.108 (3)0.112 (3)0.101 (3)0.075 (2)0.023 (2)0.007 (2)
C140.106 (2)0.096 (2)0.078 (2)0.056 (2)0.0270 (18)0.0154 (17)
C150.0540 (13)0.0454 (12)0.0397 (11)0.0062 (10)0.0063 (9)0.0083 (9)
C160.0592 (14)0.0547 (14)0.0522 (13)0.0019 (11)0.0110 (11)0.0164 (11)
C170.0540 (15)0.0788 (19)0.0704 (17)0.0001 (13)0.0183 (13)0.0195 (14)
C180.0655 (17)0.087 (2)0.0628 (16)0.0275 (15)0.0177 (13)0.0104 (14)
C190.0762 (17)0.0544 (14)0.0546 (14)0.0234 (13)0.0091 (12)0.0110 (11)
C200.0538 (13)0.0449 (12)0.0535 (13)0.0060 (10)0.0081 (10)0.0099 (10)
P20.0514 (3)0.0457 (3)0.0399 (3)0.0145 (3)0.0011 (2)0.0099 (2)
N30.0741 (14)0.0552 (12)0.0528 (12)0.0134 (11)0.0118 (10)0.0054 (10)
N40.0797 (16)0.0955 (18)0.0497 (13)0.0305 (14)0.0115 (11)0.0212 (13)
C210.131 (3)0.076 (2)0.0599 (18)0.040 (2)0.0297 (19)0.0105 (15)
C220.100 (2)0.0591 (16)0.0706 (18)0.0137 (15)0.0275 (16)0.0041 (14)
C230.0656 (15)0.0512 (13)0.0450 (12)0.0242 (11)0.0039 (11)0.0102 (10)
C240.0541 (13)0.0511 (12)0.0437 (12)0.0201 (10)0.0004 (10)0.0113 (10)
C250.0613 (15)0.0650 (15)0.0517 (14)0.0169 (12)0.0016 (11)0.0161 (12)
C260.0690 (17)0.091 (2)0.0613 (17)0.0173 (15)0.0115 (14)0.0318 (16)
C270.0821 (19)0.0720 (16)0.0451 (13)0.0389 (15)0.0019 (12)0.0106 (12)
C280.113 (3)0.089 (2)0.0459 (15)0.046 (2)0.0079 (16)0.0005 (15)
C290.0485 (12)0.0437 (11)0.0423 (11)0.0096 (9)0.0046 (9)0.0066 (9)
C300.0565 (14)0.0710 (16)0.0505 (13)0.0174 (12)0.0016 (11)0.0166 (12)
C310.0525 (15)0.0784 (18)0.0716 (17)0.0200 (13)0.0041 (13)0.0130 (15)
C320.0509 (15)0.0708 (17)0.093 (2)0.0185 (13)0.0168 (14)0.0125 (16)
C330.0710 (18)0.0775 (18)0.0796 (19)0.0197 (14)0.0203 (15)0.0284 (15)
C340.0558 (14)0.0643 (15)0.0550 (14)0.0151 (12)0.0057 (11)0.0199 (12)
C350.0473 (12)0.0491 (12)0.0387 (11)0.0152 (10)0.0005 (9)0.0112 (9)
C360.0610 (15)0.0573 (14)0.0650 (15)0.0188 (12)0.0118 (12)0.0178 (12)
C370.0668 (16)0.0730 (18)0.0808 (19)0.0118 (14)0.0299 (14)0.0225 (15)
C380.0730 (18)0.0622 (16)0.0714 (17)0.0063 (13)0.0283 (14)0.0071 (13)
C390.0841 (19)0.0503 (14)0.088 (2)0.0216 (14)0.0300 (16)0.0002 (13)
C400.0645 (15)0.0556 (14)0.0657 (15)0.0242 (12)0.0207 (12)0.0015 (12)
Geometric parameters (Å, º) top
P1—C91.833 (2)P2—C241.825 (2)
P1—C31.834 (2)P2—C291.837 (2)
P1—C151.836 (2)P2—C351.837 (2)
N1—C11.303 (3)N3—C221.308 (3)
N1—C81.362 (3)N3—C231.366 (3)
C1—C21.405 (4)N4—C261.299 (4)
C1—H1B0.9300N4—C271.365 (4)
N2—C51.308 (3)C21—C281.350 (5)
N2—C41.369 (3)C21—C221.402 (4)
C2—C31.370 (3)C21—H21A0.9300
C2—H2B0.9300C22—H22A0.9300
C3—C41.418 (3)C23—C271.413 (3)
C4—C81.406 (3)C23—C241.421 (3)
C5—C61.397 (4)C24—C251.379 (3)
C5—H5A0.9300C25—C261.403 (3)
C6—C71.350 (4)C25—H25A0.9300
C6—H6A0.9300C26—H26A0.9300
C7—C81.400 (4)C27—C281.406 (4)
C7—H7A0.9300C28—H28A0.9300
C9—C101.376 (3)C29—C341.387 (3)
C9—C141.390 (4)C29—C301.390 (3)
C10—C111.373 (3)C30—C311.384 (4)
C10—H10A0.9300C30—H30A0.9300
C11—C121.359 (4)C31—C321.362 (4)
C11—H11A0.9300C31—H31A0.9300
C12—C131.365 (5)C32—C331.368 (4)
C12—H12A0.9300C32—H32A0.9300
C13—C141.363 (4)C33—C341.389 (4)
C13—H13A0.9300C33—H33A0.9300
C14—H14A0.9300C34—H34A0.9300
C15—C161.392 (3)C35—C361.382 (3)
C15—C201.394 (3)C35—C401.390 (3)
C16—C171.375 (4)C36—C371.379 (3)
C16—H16A0.9300C36—H36A0.9300
C17—C181.380 (4)C37—C381.371 (4)
C17—H17A0.9300C37—H37A0.9300
C18—C191.381 (4)C38—C391.373 (4)
C18—H18A0.9300C38—H38A0.9300
C19—C201.377 (3)C39—C401.375 (3)
C19—H19A0.9300C39—H39A0.9300
C20—H20A0.9300C40—H40A0.9300
C9—P1—C3101.25 (10)C24—P2—C29102.48 (10)
C9—P1—C15102.27 (10)C24—P2—C35100.79 (10)
C3—P1—C15100.59 (10)C29—P2—C35102.15 (9)
C1—N1—C8116.2 (2)C22—N3—C23117.0 (2)
N1—C1—C2125.0 (3)C26—N4—C27116.4 (2)
N1—C1—H1B117.5C28—C21—C22119.5 (3)
C2—C1—H1B117.5C28—C21—H21A120.3
C5—N2—C4117.1 (2)C22—C21—H21A120.3
C3—C2—C1120.1 (2)N3—C22—C21124.0 (3)
C3—C2—H2B120.0N3—C22—H22A118.0
C1—C2—H2B120.0C21—C22—H22A118.0
C2—C3—C4116.5 (2)N3—C23—C27123.0 (2)
C2—C3—P1126.31 (18)N3—C23—C24118.4 (2)
C4—C3—P1117.19 (17)C27—C23—C24118.6 (2)
N2—C4—C8122.6 (2)C25—C24—C23116.8 (2)
N2—C4—C3118.4 (2)C25—C24—P2124.86 (18)
C8—C4—C3119.1 (2)C23—C24—P2118.21 (17)
N2—C5—C6124.3 (3)C24—C25—C26119.7 (2)
N2—C5—H5A117.9C24—C25—H25A120.2
C6—C5—H5A117.9C26—C25—H25A120.2
C7—C6—C5118.8 (2)N4—C26—C25125.3 (3)
C7—C6—H6A120.6N4—C26—H26A117.3
C5—C6—H6A120.6C25—C26—H26A117.3
C6—C7—C8119.9 (3)N4—C27—C28119.7 (3)
C6—C7—H7A120.1N4—C27—C23123.1 (2)
C8—C7—H7A120.1C28—C27—C23117.2 (3)
N1—C8—C7119.5 (2)C21—C28—C27119.4 (3)
N1—C8—C4123.2 (2)C21—C28—H28A120.3
C7—C8—C4117.3 (2)C27—C28—H28A120.3
C10—C9—C14116.6 (2)C34—C29—C30117.7 (2)
C10—C9—P1124.08 (18)C34—C29—P2124.86 (17)
C14—C9—P1119.2 (2)C30—C29—P2117.40 (17)
C11—C10—C9121.4 (2)C31—C30—C29121.4 (2)
C11—C10—H10A119.3C31—C30—H30A119.3
C9—C10—H10A119.3C29—C30—H30A119.3
C12—C11—C10120.4 (3)C32—C31—C30120.2 (2)
C12—C11—H11A119.8C32—C31—H31A119.9
C10—C11—H11A119.8C30—C31—H31A119.9
C11—C12—C13119.7 (3)C31—C32—C33119.4 (2)
C11—C12—H12A120.1C31—C32—H32A120.3
C13—C12—H12A120.1C33—C32—H32A120.3
C14—C13—C12119.8 (3)C32—C33—C34121.2 (3)
C14—C13—H13A120.1C32—C33—H33A119.4
C12—C13—H13A120.1C34—C33—H33A119.4
C13—C14—C9122.1 (3)C29—C34—C33120.1 (2)
C13—C14—H14A119.0C29—C34—H34A119.9
C9—C14—H14A119.0C33—C34—H34A119.9
C16—C15—C20118.2 (2)C36—C35—C40118.1 (2)
C16—C15—P1118.02 (17)C36—C35—P2118.21 (17)
C20—C15—P1123.79 (17)C40—C35—P2123.60 (17)
C17—C16—C15121.0 (2)C37—C36—C35121.1 (2)
C17—C16—H16A119.5C37—C36—H36A119.5
C15—C16—H16A119.5C35—C36—H36A119.5
C16—C17—C18120.1 (2)C38—C37—C36119.9 (2)
C16—C17—H17A120.0C38—C37—H37A120.0
C18—C17—H17A120.0C36—C37—H37A120.0
C17—C18—C19119.9 (2)C37—C38—C39120.0 (2)
C17—C18—H18A120.1C37—C38—H38A120.0
C19—C18—H18A120.1C39—C38—H38A120.0
C20—C19—C18120.1 (2)C38—C39—C40120.2 (2)
C20—C19—H19A120.0C38—C39—H39A119.9
C18—C19—H19A120.0C40—C39—H39A119.9
C19—C20—C15120.8 (2)C39—C40—C35120.7 (2)
C19—C20—H20A119.6C39—C40—H40A119.6
C15—C20—H20A119.6C35—C40—H40A119.6
C8—N1—C1—C20.2 (5)C23—N3—C22—C210.3 (4)
N1—C1—C2—C31.1 (5)C28—C21—C22—N30.5 (5)
C1—C2—C3—C41.0 (4)C22—N3—C23—C270.3 (4)
C1—C2—C3—P1178.6 (2)C22—N3—C23—C24179.5 (2)
C9—P1—C3—C21.9 (2)N3—C23—C24—C25179.1 (2)
C15—P1—C3—C2106.8 (2)C27—C23—C24—C251.1 (3)
C9—P1—C3—C4179.43 (17)N3—C23—C24—P22.5 (3)
C15—P1—C3—C475.65 (18)C27—C23—C24—P2177.73 (17)
C5—N2—C4—C80.3 (3)C29—P2—C24—C25110.2 (2)
C5—N2—C4—C3179.9 (2)C35—P2—C24—C255.1 (2)
C2—C3—C4—N2179.5 (2)C29—P2—C24—C2373.42 (19)
P1—C3—C4—N21.7 (3)C35—P2—C24—C23178.59 (17)
C2—C3—C4—C80.3 (3)C23—C24—C25—C260.3 (4)
P1—C3—C4—C8178.06 (17)P2—C24—C25—C26176.7 (2)
C4—N2—C5—C60.8 (4)C27—N4—C26—C251.4 (4)
N2—C5—C6—C70.5 (4)C24—C25—C26—N41.0 (4)
C5—C6—C7—C80.3 (4)C26—N4—C27—C28178.6 (3)
C1—N1—C8—C7179.3 (3)C26—N4—C27—C230.5 (4)
C1—N1—C8—C40.6 (4)N3—C23—C27—N4179.5 (2)
C6—C7—C8—N1179.4 (3)C24—C23—C27—N40.7 (4)
C6—C7—C8—C40.7 (4)N3—C23—C27—C280.4 (4)
N2—C4—C8—N1179.7 (2)C24—C23—C27—C28179.8 (2)
C3—C4—C8—N10.6 (4)C22—C21—C28—C271.2 (5)
N2—C4—C8—C70.4 (4)N4—C27—C28—C21179.7 (3)
C3—C4—C8—C7179.3 (2)C23—C27—C28—C211.2 (4)
C3—P1—C9—C10101.0 (2)C24—P2—C29—C3410.2 (2)
C15—P1—C9—C102.5 (2)C35—P2—C29—C3493.9 (2)
C3—P1—C9—C1483.5 (2)C24—P2—C29—C30168.96 (18)
C15—P1—C9—C14172.9 (2)C35—P2—C29—C3086.93 (19)
C14—C9—C10—C110.8 (4)C34—C29—C30—C310.3 (4)
P1—C9—C10—C11174.7 (2)P2—C29—C30—C31179.5 (2)
C9—C10—C11—C121.1 (5)C29—C30—C31—C320.5 (4)
C10—C11—C12—C130.8 (5)C30—C31—C32—C330.4 (4)
C11—C12—C13—C140.3 (6)C31—C32—C33—C340.1 (4)
C12—C13—C14—C90.0 (6)C30—C29—C34—C330.1 (3)
C10—C9—C14—C130.3 (5)P2—C29—C34—C33179.12 (19)
P1—C9—C14—C13175.5 (3)C32—C33—C34—C290.1 (4)
C9—P1—C15—C16106.28 (18)C24—P2—C35—C3686.70 (19)
C3—P1—C15—C16149.62 (18)C29—P2—C35—C36167.86 (17)
C9—P1—C15—C2072.8 (2)C24—P2—C35—C4096.5 (2)
C3—P1—C15—C2031.4 (2)C29—P2—C35—C408.9 (2)
C20—C15—C16—C171.0 (3)C40—C35—C36—C370.9 (4)
P1—C15—C16—C17179.93 (19)P2—C35—C36—C37177.87 (19)
C15—C16—C17—C181.7 (4)C35—C36—C37—C381.7 (4)
C16—C17—C18—C191.0 (4)C36—C37—C38—C391.1 (4)
C17—C18—C19—C200.3 (4)C37—C38—C39—C400.4 (5)
C18—C19—C20—C151.0 (4)C38—C39—C40—C351.2 (4)
C16—C15—C20—C190.4 (3)C36—C35—C40—C390.5 (4)
P1—C15—C20—C19178.64 (17)P2—C35—C40—C39176.3 (2)

Experimental details

Crystal data
Chemical formulaC20H15N2P
Mr314.31
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)10.1103 (7), 11.7020 (8), 15.7060 (11)
α, β, γ (°)71.54 (3), 75.05 (3), 71.37 (3)
V3)1644.6 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.17
Crystal size (mm)0.30 × 0.20 × 0.20
Data collection
DiffractometerEnraf–Nonius CAD-4
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.952, 0.967
No. of measured, independent and
observed [I > 2σ(I)] reflections
6393, 6024, 4473
Rint0.019
(sin θ/λ)max1)0.603
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.151, 1.00
No. of reflections6024
No. of parameters416
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.24, 0.18

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

The author thanks the Center of Test and Analysis, Nanjing University, for data collection.

References

First citationBadawneh, M., Ferrarini, P. L., Calderone, V., Manera, C., Martinotti, E., Mori, C., Saccomanni, G. & Testai, L. (2001). Eur. J. Med. Chem. 36, 925–934.  Web of Science CrossRef PubMed CAS Google Scholar
First citationChen, C., Wang, K.-Y., Jiang, P., Song, G.-L. & Zhu, H.-J. (2012). Inorg. Chem. Commun. 17, 116–119.  Web of Science CSD CrossRef CAS Google Scholar
First citationEnraf–Nonius (1994). CAD-4 EXPRESS. Enraf–Nonius, Delft, The Netherlands.  Google Scholar
First citationGoswami, S., Ghosh, K. & Mukherjee, R. (2001). Tetrahedron, 57, 4987–4993.  Web of Science CrossRef CAS Google Scholar
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First citationGoswami, S., Mukherjee, R., Mukherjee, S., Jana, S., Maity, A. C. & Adak, A. K. (2005). Molecules, 10, 929–934.  Web of Science CrossRef PubMed CAS Google Scholar
First citationHarms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.  Google Scholar
First citationHawes, E. M., Gorecki, D. K. J. & Gedir, G. G. (1977). J. Med. Chem. 20, 838–841.  CrossRef CAS PubMed Web of Science Google Scholar
First citationNorth, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.  CrossRef IUCr Journals Web of Science Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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