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

Susan J Berners-Price; Maribel Navarro; Brian W Skelton

doi:10.1107/S1600536809004590

. 2009 Feb 18;65(Pt 3):o542. doi: 10.1107/S1600536809004590

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

Susan J Berners-Price ^a, Maribel Navarro ^a,^‡, Brian W Skelton ^a,^*

PMCID: PMC2968607 PMID: 21582201

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 ▶); Barnard & Berners-Price (2007 ▶); Liu et al. (2008 ▶). The crystal structure of the parent 1,2-bis(di-2-pyridylphosphino)ethane molecule has been determined (Jones et al., 1999 ▶). The structure of 1,2-bis(di-phenylphosphino)ethane dioxide (Calcagno et al., 2000 ▶) is similar, with the two halves of the molecule related by a pseudo-inversion centre, but this is not isomorphous with the title compound.

Experimental

Crystal data

C₂₂H₂₀N₄O₂P₂
M _r = 434.36
Triclinic,
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 ▶) 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
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.34 e Å⁻³

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

Supplementary Material

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

e-65-0o542-sup1.cif^{(18.8KB, cif)}

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

e-65-0o542-Isup2.hkl^{(232.3KB, 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.

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

C₂₂H₂₀N₄O₂P₂	Z = 2
M_r = 434.36	F(000) = 452
Triclinic, P1	D_x = 1.366 Mg m⁻³
Hall symbol: -p 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.3760 (6) Å	Cell parameters from 2539 reflections
b = 8.8496 (8) Å	θ = 3.3–32.6°
c = 16.2332 (11) Å	µ = 0.23 mm⁻¹
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

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Data collection

Oxford Diffraction Gemini diffractometer	4842 independent reflections
Radiation source: sealed tube	2698 reflections with I > 2σ(I)
graphite	R_int = 0.059
ω scans	θ_max = 27.5°, θ_min = 3.3°
Absorption correction: gaussian (CrysAlis RED; Oxford Diffraction, 2008)	h = −10→10
T_min = 0.968, T_max = 0.988	k = −11→11
10983 measured reflections	l = −21→21

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Refinement

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H-atom parameters constrained
S = 0.86	w = 1/[σ²(F_o²) + (0.0495P)²] where P = (F_o² + 2F_c²)/3
4842 reflections	(Δ/σ)_max = 0.002
271 parameters	Δρ_max = 0.43 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

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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.

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

	x	y	z	U_iso*/U_eq
P1	0.18196 (9)	0.21056 (9)	0.45935 (4)	0.02233 (18)
O1	0.3253 (2)	0.3074 (2)	0.53572 (11)	0.0272 (4)
C111	0.2511 (3)	0.0876 (3)	0.37091 (16)	0.0217 (6)
N112	0.1239 (3)	−0.0366 (3)	0.30732 (14)	0.0267 (5)
C113	0.1759 (4)	−0.1218 (4)	0.24034 (17)	0.0320 (7)
H113	0.0879	−0.2109	0.195	0.038*
C114	0.3487 (4)	−0.0891 (4)	0.23254 (18)	0.0320 (7)
H114	0.3782	−0.1528	0.1831	0.038*
C115	0.4767 (4)	0.0385 (4)	0.29857 (19)	0.0372 (8)
H115	0.5969	0.0641	0.2957	0.045*
C116	0.4284 (3)	0.1287 (4)	0.36902 (18)	0.0313 (7)
H116	0.5146	0.2172	0.4153	0.038*
C121	0.1197 (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	−0.216	0.3661	0.3298	0.042*
C124	0.0236 (4)	0.5571 (4)	0.34727 (17)	0.0310 (7)
H124	−0.0142	0.6263	0.3228	0.037*
C125	0.1972 (4)	0.6111 (4)	0.37892 (17)	0.0316 (7)
H125	0.2816	0.7184	0.3773	0.038*
C126	0.2464 (3)	0.5055 (3)	0.41316 (16)	0.0256 (6)
H126	0.3659	0.5388	0.4351	0.031*
C10	−0.0180 (3)	0.0583 (3)	0.47773 (16)	0.0242 (6)
H10A	−0.0786	0.121	0.5142	0.029*
H10B	−0.0962	−0.0124	0.4216	0.029*
P2	0.68020 (8)	0.27338 (9)	0.04404 (4)	0.02132 (18)
O2	0.7095 (2)	0.3187 (2)	−0.03767 (11)	0.0278 (4)
C211	0.6499 (3)	0.4398 (3)	0.12649 (16)	0.0213 (6)
N212	0.6135 (3)	0.4071 (3)	0.20118 (14)	0.0279 (5)
C213	0.6005 (4)	0.5335 (4)	0.26420 (18)	0.0327 (7)
H213	0.5758	0.5138	0.3179	0.039*
C214	0.6210 (3)	0.6903 (4)	0.2556 (2)	0.0358 (7)
H214	0.6111	0.7759	0.3025	0.043*
C215	0.6559 (3)	0.7211 (4)	0.1781 (2)	0.0347 (7)
H215	0.6695	0.8277	0.1702	0.042*
C216	0.6707 (3)	0.5931 (4)	0.11223 (19)	0.0299 (7)
H216	0.6949	0.61	0.058	0.036*
C221	0.8672 (3)	0.2545 (3)	0.09411 (16)	0.0218 (6)
N222	0.8365 (3)	0.1354 (3)	0.13511 (14)	0.0285 (5)
C223	0.9776 (4)	0.1286 (4)	0.17259 (18)	0.0335 (7)
H223	0.9594	0.0457	0.2022	0.04*
C224	1.1484 (4)	0.2342 (4)	0.17114 (18)	0.0330 (7)
H224	1.2439	0.2227	0.1984	0.04*
C225	1.1771 (3)	0.3559 (4)	0.12949 (18)	0.0342 (7)
H225	1.2929	0.4316	0.1281	0.041*
C226	1.0340 (3)	0.3661 (4)	0.08959 (17)	0.0278 (6)
H226	1.0498	0.4481	0.0596	0.033*
C20	0.4938 (3)	0.0766 (3)	0.03363 (16)	0.0212 (6)
H20A	0.4874	0.0554	0.0905	0.025*
H20B	0.3853	0.0876	0.0159	0.025*

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Atomic displacement parameters (Å²)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0206 (4)	0.0253 (4)	0.0224 (4)	0.0096 (3)	0.0051 (3)	0.0090 (3)
O1	0.0232 (9)	0.0318 (11)	0.0235 (10)	0.0099 (9)	0.0022 (8)	0.0063 (8)
C111	0.0238 (14)	0.0239 (15)	0.0205 (13)	0.0105 (12)	0.0034 (11)	0.0107 (12)
N112	0.0328 (13)	0.0261 (14)	0.0234 (12)	0.0148 (11)	0.0026 (10)	0.0073 (11)
C113	0.0433 (18)	0.0298 (17)	0.0235 (15)	0.0168 (15)	0.0002 (13)	0.0072 (13)
C114	0.0463 (18)	0.0262 (17)	0.0295 (16)	0.0186 (15)	0.0148 (14)	0.0115 (14)
C115	0.0328 (16)	0.0311 (18)	0.050 (2)	0.0137 (14)	0.0224 (15)	0.0120 (16)
C116	0.0261 (15)	0.0256 (17)	0.0358 (17)	0.0058 (13)	0.0070 (13)	0.0063 (14)
C121	0.0250 (14)	0.0237 (15)	0.0201 (14)	0.0105 (12)	0.0067 (11)	0.0066 (12)
N122	0.0216 (12)	0.0288 (14)	0.0420 (14)	0.0083 (11)	0.0007 (10)	0.0181 (12)
C123	0.0262 (15)	0.0337 (19)	0.0480 (19)	0.0103 (14)	0.0022 (13)	0.0197 (15)
C124	0.0354 (16)	0.0282 (17)	0.0341 (16)	0.0159 (14)	0.0042 (13)	0.0128 (14)
C125	0.0342 (16)	0.0201 (16)	0.0361 (17)	0.0037 (13)	0.0084 (13)	0.0126 (13)
C126	0.0239 (14)	0.0268 (16)	0.0232 (14)	0.0083 (12)	0.0031 (11)	0.0065 (12)
C10	0.0213 (14)	0.0279 (16)	0.0256 (14)	0.0110 (12)	0.0061 (11)	0.0104 (12)
P2	0.0193 (3)	0.0198 (4)	0.0227 (4)	0.0056 (3)	0.0010 (3)	0.0071 (3)
O2	0.0289 (10)	0.0251 (11)	0.0265 (10)	0.0079 (9)	0.0018 (8)	0.0084 (9)
C211	0.0125 (12)	0.0214 (15)	0.0253 (14)	0.0052 (11)	−0.0033 (11)	0.0037 (12)
N212	0.0272 (12)	0.0358 (15)	0.0220 (12)	0.0161 (11)	−0.0015 (10)	0.0070 (11)
C213	0.0332 (16)	0.044 (2)	0.0234 (15)	0.0229 (15)	0.0014 (12)	0.0042 (14)
C214	0.0262 (15)	0.0336 (19)	0.0426 (19)	0.0162 (14)	0.0004 (14)	−0.0008 (15)
C215	0.0232 (15)	0.0180 (16)	0.057 (2)	0.0052 (12)	0.0057 (14)	0.0069 (15)
C216	0.0195 (14)	0.0267 (17)	0.0400 (17)	0.0058 (12)	0.0060 (12)	0.0104 (14)
C221	0.0225 (14)	0.0214 (15)	0.0208 (14)	0.0089 (12)	0.0039 (11)	0.0053 (12)
N222	0.0250 (12)	0.0265 (14)	0.0348 (13)	0.0087 (11)	0.0012 (10)	0.0141 (11)
C223	0.0295 (16)	0.0307 (18)	0.0421 (18)	0.0093 (14)	0.0003 (13)	0.0191 (15)
C224	0.0234 (15)	0.0388 (19)	0.0399 (18)	0.0134 (14)	−0.0027 (13)	0.0169 (15)
C225	0.0196 (14)	0.0389 (19)	0.0412 (18)	0.0069 (13)	0.0058 (13)	0.0155 (15)
C226	0.0240 (14)	0.0279 (17)	0.0321 (16)	0.0069 (13)	0.0059 (12)	0.0157 (13)
C20	0.0185 (13)	0.0212 (15)	0.0226 (14)	0.0072 (11)	−0.0002 (11)	0.0067 (11)

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Geometric parameters (Å, °)

P1—O1	1.4917 (18)	P2—O2	1.4897 (18)
P1—C10	1.799 (3)	P2—C20	1.798 (2)
P1—C121	1.809 (3)	P2—C211	1.811 (3)
P1—C111	1.815 (3)	P2—C221	1.819 (3)
C111—N112	1.344 (3)	C211—N212	1.341 (3)
C111—C116	1.391 (3)	C211—C216	1.384 (4)
N112—C113	1.339 (3)	N212—C213	1.340 (3)
C113—C114	1.381 (4)	C213—C214	1.378 (4)
C113—H113	0.95	C213—H213	0.95
C114—C115	1.377 (4)	C214—C215	1.378 (4)
C114—H114	0.95	C214—H214	0.95
C115—C116	1.380 (4)	C215—C216	1.382 (4)
C115—H115	0.95	C215—H215	0.95
C116—H116	0.95	C216—H216	0.95
C121—N122	1.352 (3)	C221—N222	1.343 (3)
C121—C126	1.383 (4)	C221—C226	1.386 (3)
N122—C123	1.339 (3)	N222—C223	1.336 (3)
C123—C124	1.382 (4)	C223—C224	1.382 (4)
C123—H123	0.95	C223—H223	0.95
C124—C125	1.371 (4)	C224—C225	1.372 (4)
C124—H124	0.95	C224—H224	0.95
C125—C126	1.381 (4)	C225—C226	1.383 (4)
C125—H125	0.95	C225—H225	0.95
C126—H126	0.95	C226—H226	0.95
C10—C10ⁱ	1.516 (5)	C20—C20ⁱⁱ	1.536 (5)
C10—H10A	0.99	C20—H20A	0.99
C10—H10B	0.99	C20—H20B	0.99

O1—P1—C10	115.87 (11)	O2—P2—C20	115.28 (11)
O1—P1—C121	112.56 (12)	O2—P2—C211	111.60 (12)
C10—P1—C121	105.88 (12)	C20—P2—C211	106.06 (11)
O1—P1—C111	110.98 (11)	O2—P2—C221	112.89 (11)
C10—P1—C111	105.53 (12)	C20—P2—C221	106.09 (12)
C121—P1—C111	105.23 (11)	C211—P2—C221	104.05 (11)
N112—C111—C116	123.1 (2)	N212—C211—C216	123.4 (2)
N112—C111—P1	116.64 (18)	N212—C211—P2	116.2 (2)
C116—C111—P1	120.2 (2)	C216—C211—P2	120.4 (2)
C113—N112—C111	116.4 (2)	C213—N212—C211	116.5 (2)
N112—C113—C114	124.6 (3)	N212—C213—C214	123.8 (3)
N112—C113—H113	117.7	N212—C213—H213	118.1
C114—C113—H113	117.7	C214—C213—H213	118.1
C115—C114—C113	118.0 (3)	C215—C214—C213	119.1 (3)
C115—C114—H114	121	C215—C214—H214	120.5
C113—C114—H114	121	C213—C214—H214	120.5
C114—C115—C116	119.3 (3)	C214—C215—C216	118.2 (3)
C114—C115—H115	120.4	C214—C215—H215	120.9
C116—C115—H115	120.4	C216—C215—H215	120.9
C115—C116—C111	118.7 (3)	C215—C216—C211	119.0 (3)
C115—C116—H116	120.6	C215—C216—H216	120.5
C111—C116—H116	120.6	C211—C216—H216	120.5
N122—C121—C126	123.0 (2)	N222—C221—C226	123.4 (2)
N122—C121—P1	117.2 (2)	N222—C221—P2	118.23 (18)
C126—C121—P1	119.86 (19)	C226—C221—P2	118.36 (19)
C123—N122—C121	116.5 (2)	C223—N222—C221	116.2 (2)
N122—C123—C124	123.6 (3)	N222—C223—C224	124.3 (3)
N122—C123—H123	118.2	N222—C223—H223	117.8
C124—C123—H123	118.2	C224—C223—H223	117.8
C125—C124—C123	119.3 (3)	C225—C224—C223	118.6 (2)
C125—C124—H124	120.4	C225—C224—H224	120.7
C123—C124—H124	120.4	C223—C224—H224	120.7
C124—C125—C126	118.4 (3)	C224—C225—C226	118.7 (3)
C124—C125—H125	120.8	C224—C225—H225	120.6
C126—C125—H125	120.8	C226—C225—H225	120.6
C125—C126—C121	119.3 (2)	C225—C226—C221	118.8 (2)
C125—C126—H126	120.4	C225—C226—H226	120.6
C121—C126—H126	120.4	C221—C226—H226	120.6
C10ⁱ—C10—P1	111.2 (2)	C20ⁱⁱ—C20—P2	111.1 (2)
C10ⁱ—C10—H10A	109.4	C20ⁱⁱ—C20—H20A	109.4
P1—C10—H10A	109.4	P2—C20—H20A	109.4
C10ⁱ—C10—H10B	109.4	C20ⁱⁱ—C20—H20B	109.4
P1—C10—H10B	109.4	P2—C20—H20B	109.4
H10A—C10—H10B	108	H20A—C20—H20B	108

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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

Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst.27, 435.
Barnard, P. J. & Berners-Price, S. J. (2007). Coord. Chem. Rev.251, 1889–1902.
Calcagno, P., Kariuki, B. M., Kitchin, S. J., Robinson, J. M. A., Philp, D. & Harris, K. D. M. (2000). Chem. Eur. J.6, 2338–2349. [DOI] [PubMed]
Johnson, C. K. (1976). ORTEPII Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.
Jones, N. D., MacFarlane, K. S., Smith, M. B., Schutte, R. P., Rettig, S. J. & James, B. R. (1999). Inorg. Chem.38, 3956–3966.
Liu, J. J., Galettis, P., Farr, A., Maharaj, L., Samarasinha, H., McGechan, A. C., Baguley, B. C., Bowen, R. J., Berners-Price, S. J. & McKeage, M. J. (2008). J. Inorg. Biochem.102, 303–310. [DOI] [PubMed]
McKeage, M. J., Berners-Price, S. J., Galettis, P., Bowen, R. J., Brouwer, W., Ding, L., Zhuang, L. & Baguley, B. C. (2000). Cancer Chemother. Pharmacol.46, 343–350. [DOI] [PubMed]
Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
Westrip, S. P. (2009). publCIF In preparation.

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

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

e-65-0o542-sup1.cif^{(18.8KB, cif)}

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

e-65-0o542-Isup2.hkl^{(232.3KB, hkl)}

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

[bb1] Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst.27, 435.

[bb2] Barnard, P. J. & Berners-Price, S. J. (2007). Coord. Chem. Rev.251, 1889–1902.

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

Susan J Berners-Price

Maribel Navarro

Brian W Skelton

Abstract

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Experimental

Crystal data

Data collection

Refinement

Supplementary Material

Acknowledgments

supplementary crystallographic information

Comment

Experimental

Refinement

Figures

Fig. 1.

Crystal data

Data collection

Refinement

Special details

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

Atomic displacement parameters (Å²)

Geometric parameters (Å, °)

Footnotes

References

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PERMALINK

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

Susan J Berners-Price

Maribel Navarro

Brian W Skelton

Abstract

Related literature

Experimental

Crystal data

Data collection

Refinement

Supplementary Material

Acknowledgments

supplementary crystallographic information

Comment

Experimental

Refinement

Figures

Fig. 1.

Crystal data

Data collection

Refinement

Special details

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

Atomic displacement parameters (Å2)

Geometric parameters (Å, °)

Footnotes

References

Associated Data

Supplementary Materials

ACTIONS

PERMALINK

RESOURCES

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

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

Atomic displacement parameters (Å²)