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Acta Crystallogr Sect E Struct Rep Online. 2009 March 1; 65(Pt 3): o542.
Published online 2009 February 18. doi:  10.1107/S1600536809004590
PMCID: PMC2968607

1,2-Bis(di-2-pyridylphosphino­yl)ethane

Abstract

The crystal structure of the title compound, C22H20N4O2P2, consists of two independent half-mol­ecules, both of which lie on crystallographic inversion centres. There are no significant differences between the two mol­ecules.

Related literature

For the anti­tumour properties of metal complexes of bidentate tertiary phosphine ligands with pyridyl substituents, see: McKeage et al. (2000 [triangle]); Barnard & Berners-Price (2007 [triangle]); Liu et al. (2008 [triangle]). The crystal structure of the parent 1,2-bis­(di-2-pyridylphosphino)ethane mol­ecule has been determined (Jones et al., 1999 [triangle]). The structure of 1,2-bis­(di-phenyl­phosphino)ethane dioxide (Calcagno et al., 2000 [triangle]) is similar, with the two halves of the mol­ecule related by a pseudo-inversion centre, but this is not isomorphous with the title compound.

An external file that holds a picture, illustration, etc.
Object name is e-65-0o542-scheme1.jpg

Experimental

Crystal data

  • C22H20N4O2P2
  • M r = 434.36
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o542-efi1.jpg
  • a = 8.3760 (6) Å
  • b = 8.8496 (8) Å
  • c = 16.2332 (11) Å
  • α = 105.627 (7)°
  • β = 92.429 (5)°
  • γ = 112.559 (7)°
  • V = 1055.67 (16) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.23 mm−1
  • T = 110 K
  • 0.22 × 0.10 × 0.06 mm

Data collection

  • Oxford Diffraction Gemini diffractometer
  • Absorption correction: Gaussian (CrysAlis RED; Oxford Diffraction, 2008 [triangle]) T min = 0.968, T max = 0.988
  • 10983 measured reflections
  • 4842 independent reflections
  • 2698 reflections with I > 2σ(I)
  • R int = 0.059

Refinement

  • R[F 2 > 2σ(F 2)] = 0.052
  • wR(F 2) = 0.112
  • S = 0.86
  • 4842 reflections
  • 271 parameters
  • H-atom parameters constrained
  • Δρmax = 0.43 e Å−3
  • Δρmin = −0.34 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 [triangle]); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 [triangle]); data reduction: CrysAlis RED; program(s) used to solve structure: SIR92 (Altomare et al., 1994 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEPII (Johnson, 1976 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809004590/fj2193sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809004590/fj2193Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors thank the Australian Research Council for financial assistance.

supplementary crystallographic information

Comment

Bidentate tertiary phosphine ligands with pyridyl substituents, such as 1,2-bis(di-2-pyridylphosphino)ethane (d2pype) are of interest because a number of studies have shown that metal complexes with these ligands exhibit selective anti-tumour properties (McKeage et al., 2000; Barnard and Berners-Price 2007; Liu et al., 2008). During the course of our work in this area, we obtained crystals of the phosphine oxide d2pypeO2 (I), which were suitable for X-ray diffraction studies.

Experimental

1,2-bis(di-2-pyridylphosphino)ethane (d2pype) was obtained from Strem Chemicals Inc. Single crystals of the title compound d2pypeO2 (I) suitable for X-ray crystallographic analysis were obtained as a by-product of slow evaporation of a solution of d2pype and copper (I) iodide (molar ratio 2:1) in acetonitrile-tetrahydrofuran mixture.

Refinement

The assignments of the py ring N,C atoms were made on the basis of refinement and location of the H atoms. All H atoms were positioned geometrically and refined using a riding model with C—H = 0.95–0.99 Å and with Uiso(H) = 1.2 times Ueq(C).

Figures

Fig. 1.
ORTEP drawing and atom labelling for molecule n = 1. Displacement ellipsoids of non-H atoms are drawn at the 50% probablility level. The structure of the second, n = 2, molecule is very similar.

Crystal data

C22H20N4O2P2Z = 2
Mr = 434.36F(000) = 452
Triclinic, P1Dx = 1.366 Mg m3
Hall symbol: -p 1Mo Kα radiation, λ = 0.71073 Å
a = 8.3760 (6) ÅCell parameters from 2539 reflections
b = 8.8496 (8) Åθ = 3.3–32.6°
c = 16.2332 (11) ŵ = 0.23 mm1
α = 105.627 (7)°T = 110 K
β = 92.429 (5)°Plate, colourless
γ = 112.559 (7)°0.22 × 0.10 × 0.06 mm
V = 1055.67 (16) Å3

Data collection

Oxford Diffraction Gemini diffractometer4842 independent reflections
Radiation source: sealed tube2698 reflections with I > 2σ(I)
graphiteRint = 0.059
ω scansθmax = 27.5°, θmin = 3.3°
Absorption correction: gaussian (CrysAlis RED; Oxford Diffraction, 2008)h = −10→10
Tmin = 0.968, Tmax = 0.988k = −11→11
10983 measured reflectionsl = −21→21

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112H-atom parameters constrained
S = 0.86w = 1/[σ2(Fo2) + (0.0495P)2] where P = (Fo2 + 2Fc2)/3
4842 reflections(Δ/σ)max = 0.002
271 parametersΔρmax = 0.43 e Å3
0 restraintsΔρmin = −0.34 e Å3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
P10.18196 (9)0.21056 (9)0.45935 (4)0.02233 (18)
O10.3253 (2)0.3074 (2)0.53572 (11)0.0272 (4)
C1110.2511 (3)0.0876 (3)0.37091 (16)0.0217 (6)
N1120.1239 (3)−0.0366 (3)0.30732 (14)0.0267 (5)
C1130.1759 (4)−0.1218 (4)0.24034 (17)0.0320 (7)
H1130.0879−0.21090.1950.038*
C1140.3487 (4)−0.0891 (4)0.23254 (18)0.0320 (7)
H1140.3782−0.15280.18310.038*
C1150.4767 (4)0.0385 (4)0.29857 (19)0.0372 (8)
H1150.59690.06410.29570.045*
C1160.4284 (3)0.1287 (4)0.36902 (18)0.0313 (7)
H1160.51460.21720.41530.038*
C1210.1197 (3)0.3509 (3)0.41523 (15)0.0227 (6)
N122−0.0518 (3)0.2959 (3)0.38395 (15)0.0300 (6)
C123−0.0959 (4)0.4009 (4)0.35135 (19)0.0352 (7)
H123−0.2160.36610.32980.042*
C1240.0236 (4)0.5571 (4)0.34727 (17)0.0310 (7)
H124−0.01420.62630.32280.037*
C1250.1972 (4)0.6111 (4)0.37892 (17)0.0316 (7)
H1250.28160.71840.37730.038*
C1260.2464 (3)0.5055 (3)0.41316 (16)0.0256 (6)
H1260.36590.53880.43510.031*
C10−0.0180 (3)0.0583 (3)0.47773 (16)0.0242 (6)
H10A−0.07860.1210.51420.029*
H10B−0.0962−0.01240.42160.029*
P20.68020 (8)0.27338 (9)0.04404 (4)0.02132 (18)
O20.7095 (2)0.3187 (2)−0.03767 (11)0.0278 (4)
C2110.6499 (3)0.4398 (3)0.12649 (16)0.0213 (6)
N2120.6135 (3)0.4071 (3)0.20118 (14)0.0279 (5)
C2130.6005 (4)0.5335 (4)0.26420 (18)0.0327 (7)
H2130.57580.51380.31790.039*
C2140.6210 (3)0.6903 (4)0.2556 (2)0.0358 (7)
H2140.61110.77590.30250.043*
C2150.6559 (3)0.7211 (4)0.1781 (2)0.0347 (7)
H2150.66950.82770.17020.042*
C2160.6707 (3)0.5931 (4)0.11223 (19)0.0299 (7)
H2160.69490.610.0580.036*
C2210.8672 (3)0.2545 (3)0.09411 (16)0.0218 (6)
N2220.8365 (3)0.1354 (3)0.13511 (14)0.0285 (5)
C2230.9776 (4)0.1286 (4)0.17259 (18)0.0335 (7)
H2230.95940.04570.20220.04*
C2241.1484 (4)0.2342 (4)0.17114 (18)0.0330 (7)
H2241.24390.22270.19840.04*
C2251.1771 (3)0.3559 (4)0.12949 (18)0.0342 (7)
H2251.29290.43160.12810.041*
C2261.0340 (3)0.3661 (4)0.08959 (17)0.0278 (6)
H2261.04980.44810.05960.033*
C200.4938 (3)0.0766 (3)0.03363 (16)0.0212 (6)
H20A0.48740.05540.09050.025*
H20B0.38530.08760.01590.025*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
P10.0206 (4)0.0253 (4)0.0224 (4)0.0096 (3)0.0051 (3)0.0090 (3)
O10.0232 (9)0.0318 (11)0.0235 (10)0.0099 (9)0.0022 (8)0.0063 (8)
C1110.0238 (14)0.0239 (15)0.0205 (13)0.0105 (12)0.0034 (11)0.0107 (12)
N1120.0328 (13)0.0261 (14)0.0234 (12)0.0148 (11)0.0026 (10)0.0073 (11)
C1130.0433 (18)0.0298 (17)0.0235 (15)0.0168 (15)0.0002 (13)0.0072 (13)
C1140.0463 (18)0.0262 (17)0.0295 (16)0.0186 (15)0.0148 (14)0.0115 (14)
C1150.0328 (16)0.0311 (18)0.050 (2)0.0137 (14)0.0224 (15)0.0120 (16)
C1160.0261 (15)0.0256 (17)0.0358 (17)0.0058 (13)0.0070 (13)0.0063 (14)
C1210.0250 (14)0.0237 (15)0.0201 (14)0.0105 (12)0.0067 (11)0.0066 (12)
N1220.0216 (12)0.0288 (14)0.0420 (14)0.0083 (11)0.0007 (10)0.0181 (12)
C1230.0262 (15)0.0337 (19)0.0480 (19)0.0103 (14)0.0022 (13)0.0197 (15)
C1240.0354 (16)0.0282 (17)0.0341 (16)0.0159 (14)0.0042 (13)0.0128 (14)
C1250.0342 (16)0.0201 (16)0.0361 (17)0.0037 (13)0.0084 (13)0.0126 (13)
C1260.0239 (14)0.0268 (16)0.0232 (14)0.0083 (12)0.0031 (11)0.0065 (12)
C100.0213 (14)0.0279 (16)0.0256 (14)0.0110 (12)0.0061 (11)0.0104 (12)
P20.0193 (3)0.0198 (4)0.0227 (4)0.0056 (3)0.0010 (3)0.0071 (3)
O20.0289 (10)0.0251 (11)0.0265 (10)0.0079 (9)0.0018 (8)0.0084 (9)
C2110.0125 (12)0.0214 (15)0.0253 (14)0.0052 (11)−0.0033 (11)0.0037 (12)
N2120.0272 (12)0.0358 (15)0.0220 (12)0.0161 (11)−0.0015 (10)0.0070 (11)
C2130.0332 (16)0.044 (2)0.0234 (15)0.0229 (15)0.0014 (12)0.0042 (14)
C2140.0262 (15)0.0336 (19)0.0426 (19)0.0162 (14)0.0004 (14)−0.0008 (15)
C2150.0232 (15)0.0180 (16)0.057 (2)0.0052 (12)0.0057 (14)0.0069 (15)
C2160.0195 (14)0.0267 (17)0.0400 (17)0.0058 (12)0.0060 (12)0.0104 (14)
C2210.0225 (14)0.0214 (15)0.0208 (14)0.0089 (12)0.0039 (11)0.0053 (12)
N2220.0250 (12)0.0265 (14)0.0348 (13)0.0087 (11)0.0012 (10)0.0141 (11)
C2230.0295 (16)0.0307 (18)0.0421 (18)0.0093 (14)0.0003 (13)0.0191 (15)
C2240.0234 (15)0.0388 (19)0.0399 (18)0.0134 (14)−0.0027 (13)0.0169 (15)
C2250.0196 (14)0.0389 (19)0.0412 (18)0.0069 (13)0.0058 (13)0.0155 (15)
C2260.0240 (14)0.0279 (17)0.0321 (16)0.0069 (13)0.0059 (12)0.0157 (13)
C200.0185 (13)0.0212 (15)0.0226 (14)0.0072 (11)−0.0002 (11)0.0067 (11)

Geometric parameters (Å, °)

P1—O11.4917 (18)P2—O21.4897 (18)
P1—C101.799 (3)P2—C201.798 (2)
P1—C1211.809 (3)P2—C2111.811 (3)
P1—C1111.815 (3)P2—C2211.819 (3)
C111—N1121.344 (3)C211—N2121.341 (3)
C111—C1161.391 (3)C211—C2161.384 (4)
N112—C1131.339 (3)N212—C2131.340 (3)
C113—C1141.381 (4)C213—C2141.378 (4)
C113—H1130.95C213—H2130.95
C114—C1151.377 (4)C214—C2151.378 (4)
C114—H1140.95C214—H2140.95
C115—C1161.380 (4)C215—C2161.382 (4)
C115—H1150.95C215—H2150.95
C116—H1160.95C216—H2160.95
C121—N1221.352 (3)C221—N2221.343 (3)
C121—C1261.383 (4)C221—C2261.386 (3)
N122—C1231.339 (3)N222—C2231.336 (3)
C123—C1241.382 (4)C223—C2241.382 (4)
C123—H1230.95C223—H2230.95
C124—C1251.371 (4)C224—C2251.372 (4)
C124—H1240.95C224—H2240.95
C125—C1261.381 (4)C225—C2261.383 (4)
C125—H1250.95C225—H2250.95
C126—H1260.95C226—H2260.95
C10—C10i1.516 (5)C20—C20ii1.536 (5)
C10—H10A0.99C20—H20A0.99
C10—H10B0.99C20—H20B0.99
O1—P1—C10115.87 (11)O2—P2—C20115.28 (11)
O1—P1—C121112.56 (12)O2—P2—C211111.60 (12)
C10—P1—C121105.88 (12)C20—P2—C211106.06 (11)
O1—P1—C111110.98 (11)O2—P2—C221112.89 (11)
C10—P1—C111105.53 (12)C20—P2—C221106.09 (12)
C121—P1—C111105.23 (11)C211—P2—C221104.05 (11)
N112—C111—C116123.1 (2)N212—C211—C216123.4 (2)
N112—C111—P1116.64 (18)N212—C211—P2116.2 (2)
C116—C111—P1120.2 (2)C216—C211—P2120.4 (2)
C113—N112—C111116.4 (2)C213—N212—C211116.5 (2)
N112—C113—C114124.6 (3)N212—C213—C214123.8 (3)
N112—C113—H113117.7N212—C213—H213118.1
C114—C113—H113117.7C214—C213—H213118.1
C115—C114—C113118.0 (3)C215—C214—C213119.1 (3)
C115—C114—H114121C215—C214—H214120.5
C113—C114—H114121C213—C214—H214120.5
C114—C115—C116119.3 (3)C214—C215—C216118.2 (3)
C114—C115—H115120.4C214—C215—H215120.9
C116—C115—H115120.4C216—C215—H215120.9
C115—C116—C111118.7 (3)C215—C216—C211119.0 (3)
C115—C116—H116120.6C215—C216—H216120.5
C111—C116—H116120.6C211—C216—H216120.5
N122—C121—C126123.0 (2)N222—C221—C226123.4 (2)
N122—C121—P1117.2 (2)N222—C221—P2118.23 (18)
C126—C121—P1119.86 (19)C226—C221—P2118.36 (19)
C123—N122—C121116.5 (2)C223—N222—C221116.2 (2)
N122—C123—C124123.6 (3)N222—C223—C224124.3 (3)
N122—C123—H123118.2N222—C223—H223117.8
C124—C123—H123118.2C224—C223—H223117.8
C125—C124—C123119.3 (3)C225—C224—C223118.6 (2)
C125—C124—H124120.4C225—C224—H224120.7
C123—C124—H124120.4C223—C224—H224120.7
C124—C125—C126118.4 (3)C224—C225—C226118.7 (3)
C124—C125—H125120.8C224—C225—H225120.6
C126—C125—H125120.8C226—C225—H225120.6
C125—C126—C121119.3 (2)C225—C226—C221118.8 (2)
C125—C126—H126120.4C225—C226—H226120.6
C121—C126—H126120.4C221—C226—H226120.6
C10i—C10—P1111.2 (2)C20ii—C20—P2111.1 (2)
C10i—C10—H10A109.4C20ii—C20—H20A109.4
P1—C10—H10A109.4P2—C20—H20A109.4
C10i—C10—H10B109.4C20ii—C20—H20B109.4
P1—C10—H10B109.4P2—C20—H20B109.4
H10A—C10—H10B108H20A—C20—H20B108

Symmetry codes: (i) −x, −y, −z+1; (ii) −x+1, −y, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FJ2193).

References

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  • Westrip, S. P. (2009). publCIF In preparation.

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