Crystal structure of 2,5-bis-(di-phenyl-phosphan-yl)furan.

In the title compound, C28H22OP2, each of the P atoms has an almost perfect pyramidal geometry, with C-P-C angles varying from 100.63 (10) to 102.65 (9)°. In the crystal, neighbouring mol-ecules are linked via weak C-H⋯π inter-actions, forming supra-molecular chains along the b-axis direction.

Related literature

For the uses of rigid diphosphine compounds in the preparation of homo- or hetero-bimetallic complexes, which have high potential for specific applications in catalytic processes, see: Kaeser et al. (2013 ▸); Xu et al. (2014 ▸). For the structural characteristics of these ligands providing control over the distance separating the two metallic centers and consequently, over the properties of the corresponding complexes, see: Brown & Lucy (1986 ▸). For the synthesis of bis­(di­phenyl­phosphan­yl)furan, see: Brown & Canning (1983 ▸). For the resulting bimetallic complexes with Rh and Ir, see: Brown et al. (1984 ▸). For C—H⋯π inter­actions, see: Munshi & Guru Row (2005 ▸).

Experimental

Crystal data

C28H22OP2

M = 436.40

Monoclinic,

a = 10.7179 (9) Å

b = 8.5559 (7) Å

c = 24.550 (2) Å

β = 94.309 (1)°

V = 2244.9 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 100 K

0.17 × 0.15 × 0.12 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▸) T min = 0.965, T max = 0.975

17894 measured reflections

3952 independent reflections

3836 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.106

S = 1.17

3952 reflections

280 parameters

H-atom parameters constrained

Δρmax = 0.49 e Å−3

Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 2000 ▸); cell refinement: SAINT (Bruker, 2000 ▸); data reduction: SAINT; 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, PLATON (Spek, 2009 ▸) and publCIF (Westrip, 2010 ▸).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015020964/su5229sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015020964/su5229Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015020964/su5229Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015020964/su5229fig1.tif

The mol­ecular structure of the title compound, with atom labeling. Displacement ellipsoids are drawn at the 50% probability level.

Click here for additional data file.

. DOI: 10.1107/S2056989015020964/su5229fig2.tif

View of the C—H⋯ π inter­actions (dashed lines; see Table 1) linking adjacent mol­ecules. Hydrogen atoms not involved in these inter­actions have been omitted for clarity.

CCDC reference: 1435225

Additional supporting information: crystallographic information; 3D view; checkCIF report

C28H22OP2	F(000) = 912
Mr = 436.40	Dx = 1.291 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7667 reflections
a = 10.7179 (9) Å	θ = 2.4–28.3°
b = 8.5559 (7) Å	µ = 0.21 mm−1
c = 24.550 (2) Å	T = 100 K
β = 94.309 (1)°	Block, colorless
V = 2244.9 (3) Å3	0.17 × 0.15 × 0.12 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	3952 independent reflections
Radiation source: fine-focus sealed tube	3836 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
Detector resolution: 8.3 pixels mm-1	θmax = 25.0°, θmin = 1.9°
phi and ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2000)	k = −9→10
Tmin = 0.965, Tmax = 0.975	l = −29→29
17894 measured reflections

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106	H-atom parameters constrained
S = 1.17	w = 1/[σ2(Fo2) + (0.0276P)2 + 1.9895P] where P = (Fo2 + 2Fc2)/3
3952 reflections	(Δ/σ)max = 0.001
280 parameters	Δρmax = 0.49 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.19328 (18)	0.3613 (2)	0.06380 (8)	0.0188 (4)
C2	0.22310 (19)	0.4340 (2)	0.01764 (8)	0.0209 (4)
H2	0.1689	0.4962	−0.0058	0.025*
C3	0.35086 (19)	0.3998 (2)	0.01087 (8)	0.0213 (4)
H3	0.3976	0.4334	−0.0184	0.026*
C4	0.39337 (18)	0.3108 (2)	0.05365 (8)	0.0191 (4)
C5	0.08909 (18)	0.3614 (2)	0.16627 (8)	0.0205 (4)
C6	0.0223 (2)	0.2789 (3)	0.20342 (9)	0.0247 (5)
H6	−0.0398	0.2060	0.1904	0.030*
C7	0.0456 (2)	0.3020 (3)	0.25921 (9)	0.0270 (5)
H7	−0.0005	0.2448	0.2841	0.032*
C8	0.1353 (2)	0.4078 (3)	0.27864 (9)	0.0270 (5)
H8	0.1505	0.4242	0.3168	0.032*
C9	0.2031 (2)	0.4898 (3)	0.24222 (9)	0.0284 (5)
H9	0.2658	0.5617	0.2555	0.034*
C10	0.18003 (19)	0.4675 (3)	0.18634 (9)	0.0249 (5)
H10	0.2265	0.5249	0.1616	0.030*
C11	0.01519 (19)	0.1311 (2)	0.08714 (8)	0.0202 (4)
C12	0.09903 (19)	0.0193 (3)	0.10970 (9)	0.0234 (5)
H12	0.1751	0.0516	0.1288	0.028*
C13	0.0715 (2)	−0.1378 (3)	0.10433 (9)	0.0270 (5)
H13	0.1291	−0.2131	0.1197	0.032*
C14	−0.0391 (2)	−0.1867 (3)	0.07683 (9)	0.0292 (5)
H14	−0.0577	−0.2950	0.0736	0.035*
C15	−0.1225 (2)	−0.0770 (3)	0.05413 (9)	0.0303 (5)
H15	−0.1984	−0.1100	0.0351	0.036*
C16	−0.0955 (2)	0.0810 (3)	0.05923 (9)	0.0248 (5)
H16	−0.1530	0.1558	0.0435	0.030*
C17	0.5853 (2)	0.3097 (2)	0.14057 (9)	0.0252 (5)
C18	0.5087 (2)	0.2928 (3)	0.18342 (10)	0.0378 (6)
H18	0.4317	0.2381	0.1777	0.045*
C19	0.5435 (3)	0.3546 (4)	0.23426 (12)	0.0595 (9)
H19	0.4902	0.3431	0.2632	0.071*
C20	0.6558 (3)	0.4332 (4)	0.24305 (15)	0.0698 (12)
H20	0.6795	0.4757	0.2781	0.084*
C21	0.7333 (3)	0.4501 (3)	0.20137 (15)	0.0592 (10)
H21	0.8108	0.5034	0.2077	0.071*
C22	0.6986 (2)	0.3893 (3)	0.15011 (12)	0.0390 (6)
H22	0.7521	0.4019	0.1213	0.047*
C23	0.51056 (19)	0.0292 (2)	0.08703 (8)	0.0205 (4)
C24	0.4083 (2)	−0.0493 (3)	0.06230 (9)	0.0264 (5)
H24	0.3509	0.0047	0.0376	0.032*
C25	0.3891 (2)	−0.2063 (3)	0.07329 (10)	0.0316 (5)
H25	0.3185	−0.2588	0.0562	0.038*
C26	0.4717 (2)	−0.2864 (3)	0.10876 (10)	0.0349 (6)
H26	0.4575	−0.3932	0.1168	0.042*
C27	0.5758 (3)	−0.2098 (3)	0.13253 (11)	0.0405 (6)
H27	0.6346	−0.2650	0.1562	0.049*
C28	0.5942 (2)	−0.0540 (3)	0.12202 (10)	0.0315 (5)
H28	0.6653	−0.0022	0.1390	0.038*
O1	0.29720 (12)	0.28470 (16)	0.08728 (6)	0.0202 (3)
P1	0.04394 (5)	0.34210 (6)	0.09286 (2)	0.02035 (15)
P2	0.54811 (5)	0.23216 (6)	0.07140 (2)	0.02108 (15)

	U11	U22	U33	U12	U13	U23
C1	0.0193 (10)	0.0148 (10)	0.0221 (10)	0.0016 (8)	−0.0010 (8)	−0.0015 (8)
C2	0.0247 (11)	0.0151 (10)	0.0223 (11)	−0.0027 (8)	−0.0027 (8)	0.0022 (8)
C3	0.0237 (10)	0.0190 (11)	0.0213 (11)	−0.0057 (8)	0.0022 (8)	0.0015 (8)
C4	0.0197 (10)	0.0165 (10)	0.0215 (10)	−0.0032 (8)	0.0041 (8)	−0.0015 (8)
C5	0.0174 (10)	0.0204 (11)	0.0238 (11)	0.0051 (8)	0.0017 (8)	−0.0031 (9)
C6	0.0223 (11)	0.0248 (12)	0.0270 (11)	−0.0023 (9)	0.0018 (9)	−0.0008 (9)
C7	0.0258 (11)	0.0301 (13)	0.0257 (12)	0.0011 (9)	0.0054 (9)	0.0008 (9)
C8	0.0251 (11)	0.0324 (13)	0.0233 (11)	0.0058 (10)	0.0002 (9)	−0.0058 (9)
C9	0.0235 (11)	0.0268 (12)	0.0345 (13)	−0.0017 (9)	0.0006 (9)	−0.0091 (10)
C10	0.0225 (11)	0.0214 (11)	0.0310 (12)	−0.0001 (9)	0.0039 (9)	−0.0013 (9)
C11	0.0215 (10)	0.0213 (11)	0.0182 (10)	−0.0021 (8)	0.0046 (8)	−0.0014 (8)
C12	0.0204 (10)	0.0246 (12)	0.0253 (11)	−0.0011 (9)	0.0016 (8)	0.0021 (9)
C13	0.0304 (12)	0.0229 (12)	0.0284 (12)	0.0034 (9)	0.0058 (9)	0.0046 (9)
C14	0.0380 (13)	0.0228 (12)	0.0274 (12)	−0.0071 (10)	0.0062 (10)	−0.0034 (9)
C15	0.0304 (12)	0.0308 (13)	0.0288 (12)	−0.0080 (10)	−0.0026 (10)	−0.0057 (10)
C16	0.0243 (11)	0.0274 (12)	0.0227 (11)	0.0000 (9)	0.0012 (9)	−0.0002 (9)
C17	0.0244 (11)	0.0183 (11)	0.0318 (12)	0.0071 (9)	−0.0049 (9)	−0.0025 (9)
C18	0.0348 (13)	0.0491 (16)	0.0288 (13)	0.0103 (12)	−0.0022 (10)	−0.0075 (11)
C19	0.060 (2)	0.083 (2)	0.0337 (15)	0.0341 (18)	−0.0099 (14)	−0.0188 (15)
C20	0.075 (2)	0.064 (2)	0.064 (2)	0.0447 (19)	−0.0437 (19)	−0.0425 (18)
C21	0.0466 (17)	0.0303 (15)	0.094 (3)	0.0147 (13)	−0.0409 (18)	−0.0256 (16)
C22	0.0279 (12)	0.0226 (13)	0.0642 (18)	0.0055 (10)	−0.0130 (12)	−0.0052 (12)
C23	0.0235 (10)	0.0174 (11)	0.0215 (11)	0.0031 (8)	0.0076 (8)	−0.0015 (8)
C24	0.0282 (12)	0.0214 (12)	0.0294 (12)	0.0034 (9)	0.0009 (9)	−0.0032 (9)
C25	0.0338 (13)	0.0218 (12)	0.0403 (14)	−0.0028 (10)	0.0104 (11)	−0.0096 (10)
C26	0.0528 (16)	0.0179 (12)	0.0360 (13)	0.0050 (11)	0.0173 (12)	0.0014 (10)
C27	0.0542 (16)	0.0285 (14)	0.0375 (14)	0.0123 (12)	−0.0063 (12)	0.0038 (11)
C28	0.0349 (13)	0.0259 (12)	0.0325 (13)	0.0035 (10)	−0.0055 (10)	0.0000 (10)
O1	0.0189 (7)	0.0204 (8)	0.0214 (7)	0.0014 (6)	0.0039 (6)	0.0043 (6)
P1	0.0184 (3)	0.0194 (3)	0.0232 (3)	0.0013 (2)	0.0013 (2)	0.0004 (2)
P2	0.0185 (3)	0.0207 (3)	0.0244 (3)	0.0002 (2)	0.0041 (2)	0.0021 (2)

C1—C2	1.352 (3)	C14—H14	0.9500
C1—O1	1.381 (2)	C15—C16	1.386 (3)
C1—P1	1.808 (2)	C15—H15	0.9500
C2—C3	1.422 (3)	C16—H16	0.9500
C2—H2	0.9500	C17—C18	1.390 (3)
C3—C4	1.349 (3)	C17—C22	1.396 (3)
C3—H3	0.9500	C17—P2	1.839 (2)
C4—O1	1.386 (2)	C18—C19	1.381 (4)
C4—P2	1.812 (2)	C18—H18	0.9500
C5—C6	1.393 (3)	C19—C20	1.382 (5)
C5—C10	1.395 (3)	C19—H19	0.9500
C5—P1	1.838 (2)	C20—C21	1.373 (5)
C6—C7	1.388 (3)	C20—H20	0.9500
C6—H6	0.9500	C21—C22	1.387 (4)
C7—C8	1.379 (3)	C21—H21	0.9500
C7—H7	0.9500	C22—H22	0.9500
C8—C9	1.385 (3)	C23—C24	1.386 (3)
C8—H8	0.9500	C23—C28	1.390 (3)
C9—C10	1.389 (3)	C23—P2	1.830 (2)
C9—H9	0.9500	C24—C25	1.388 (3)
C10—H10	0.9500	C24—H24	0.9500
C11—C16	1.392 (3)	C25—C26	1.377 (4)
C11—C12	1.398 (3)	C25—H25	0.9500
C11—P1	1.835 (2)	C26—C27	1.384 (4)
C12—C13	1.380 (3)	C26—H26	0.9500
C12—H12	0.9500	C27—C28	1.375 (4)
C13—C14	1.385 (3)	C27—H27	0.9500
C13—H13	0.9500	C28—H28	0.9500
C14—C15	1.384 (3)
C2—C1—O1	109.54 (17)	C15—C16—H16	119.7
C2—C1—P1	130.13 (16)	C11—C16—H16	119.7
O1—C1—P1	120.16 (14)	C18—C17—C22	118.7 (2)
C1—C2—C3	107.06 (18)	C18—C17—P2	124.21 (18)
C1—C2—H2	126.5	C22—C17—P2	117.14 (19)
C3—C2—H2	126.5	C19—C18—C17	120.6 (3)
C4—C3—C2	107.29 (18)	C19—C18—H18	119.7
C4—C3—H3	126.4	C17—C18—H18	119.7
C2—C3—H3	126.4	C18—C19—C20	120.0 (3)
C3—C4—O1	109.38 (17)	C18—C19—H19	120.0
C3—C4—P2	130.27 (16)	C20—C19—H19	120.0
O1—C4—P2	120.34 (14)	C21—C20—C19	120.2 (3)
C6—C5—C10	118.57 (19)	C21—C20—H20	119.9
C6—C5—P1	119.10 (16)	C19—C20—H20	119.9
C10—C5—P1	122.02 (16)	C20—C21—C22	120.0 (3)
C7—C6—C5	120.7 (2)	C20—C21—H21	120.0
C7—C6—H6	119.6	C22—C21—H21	120.0
C5—C6—H6	119.6	C21—C22—C17	120.4 (3)
C8—C7—C6	120.3 (2)	C21—C22—H22	119.8
C8—C7—H7	119.9	C17—C22—H22	119.8
C6—C7—H7	119.9	C24—C23—C28	118.4 (2)
C7—C8—C9	119.7 (2)	C24—C23—P2	123.17 (16)
C7—C8—H8	120.2	C28—C23—P2	118.26 (17)
C9—C8—H8	120.2	C23—C24—C25	120.5 (2)
C8—C9—C10	120.3 (2)	C23—C24—H24	119.8
C8—C9—H9	119.8	C25—C24—H24	119.8
C10—C9—H9	119.8	C26—C25—C24	120.5 (2)
C9—C10—C5	120.4 (2)	C26—C25—H25	119.8
C9—C10—H10	119.8	C24—C25—H25	119.8
C5—C10—H10	119.8	C25—C26—C27	119.3 (2)
C16—C11—C12	118.9 (2)	C25—C26—H26	120.3
C16—C11—P1	118.21 (16)	C27—C26—H26	120.3
C12—C11—P1	122.94 (16)	C28—C27—C26	120.2 (2)
C13—C12—C11	120.2 (2)	C28—C27—H27	119.9
C13—C12—H12	119.9	C26—C27—H27	119.9
C11—C12—H12	119.9	C27—C28—C23	121.1 (2)
C12—C13—C14	120.6 (2)	C27—C28—H28	119.4
C12—C13—H13	119.7	C23—C28—H28	119.4
C14—C13—H13	119.7	C1—O1—C4	106.71 (15)
C15—C14—C13	119.7 (2)	C1—P1—C11	101.99 (9)
C15—C14—H14	120.1	C1—P1—C5	101.71 (9)
C13—C14—H14	120.1	C11—P1—C5	101.16 (9)
C14—C15—C16	120.0 (2)	C4—P2—C23	101.00 (9)
C14—C15—H15	120.0	C4—P2—C17	102.65 (9)
C16—C15—H15	120.0	C23—P2—C17	100.63 (10)
C15—C16—C11	120.6 (2)
O1—C1—C2—C3	1.1 (2)	C25—C26—C27—C28	1.9 (4)
P1—C1—C2—C3	−173.96 (16)	C26—C27—C28—C23	−0.9 (4)
C1—C2—C3—C4	−1.2 (2)	C24—C23—C28—C27	−0.7 (3)
C2—C3—C4—O1	0.8 (2)	P2—C23—C28—C27	−175.58 (19)
C2—C3—C4—P2	−177.79 (16)	C2—C1—O1—C4	−0.7 (2)
C10—C5—C6—C7	0.1 (3)	P1—C1—O1—C4	175.01 (14)
P1—C5—C6—C7	−173.69 (16)	C3—C4—O1—C1	−0.1 (2)
C5—C6—C7—C8	0.2 (3)	P2—C4—O1—C1	178.63 (14)
C6—C7—C8—C9	−0.6 (3)	C2—C1—P1—C11	114.0 (2)
C7—C8—C9—C10	0.8 (3)	O1—C1—P1—C11	−60.70 (17)
C8—C9—C10—C5	−0.5 (3)	C2—C1—P1—C5	−141.8 (2)
C6—C5—C10—C9	0.1 (3)	O1—C1—P1—C5	43.55 (17)
P1—C5—C10—C9	173.68 (16)	C16—C11—P1—C1	−124.03 (16)
C16—C11—C12—C13	−0.2 (3)	C12—C11—P1—C1	56.25 (19)
P1—C11—C12—C13	179.52 (16)	C16—C11—P1—C5	131.29 (16)
C11—C12—C13—C14	−0.2 (3)	C12—C11—P1—C5	−48.43 (18)
C12—C13—C14—C15	0.5 (3)	C6—C5—P1—C1	−147.20 (17)
C13—C14—C15—C16	−0.4 (3)	C10—C5—P1—C1	39.21 (19)
C14—C15—C16—C11	−0.1 (3)	C6—C5—P1—C11	−42.30 (18)
C12—C11—C16—C15	0.4 (3)	C10—C5—P1—C11	144.11 (17)
P1—C11—C16—C15	−179.37 (17)	C3—C4—P2—C23	−132.8 (2)
C22—C17—C18—C19	0.6 (4)	O1—C4—P2—C23	48.70 (17)
P2—C17—C18—C19	−180.0 (2)	C3—C4—P2—C17	123.5 (2)
C17—C18—C19—C20	−0.5 (4)	O1—C4—P2—C17	−54.96 (17)
C18—C19—C20—C21	−0.1 (5)	C24—C23—P2—C4	30.32 (19)
C19—C20—C21—C22	0.5 (4)	C28—C23—P2—C4	−155.10 (17)
C20—C21—C22—C17	−0.5 (4)	C24—C23—P2—C17	135.60 (18)
C18—C17—C22—C21	−0.1 (3)	C28—C23—P2—C17	−49.82 (18)
P2—C17—C22—C21	−179.55 (19)	C18—C17—P2—C4	53.1 (2)
C28—C23—C24—C25	1.3 (3)	C22—C17—P2—C4	−127.44 (18)
P2—C23—C24—C25	175.88 (16)	C18—C17—P2—C23	−50.9 (2)
C23—C24—C25—C26	−0.3 (3)	C22—C17—P2—C23	128.61 (18)
C24—C25—C26—C27	−1.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C27—H27···Cgi	0.95	3.11	3.736 (3)	125

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of ring C17–C22.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C27—H27⋯Cg i	0.95	3.11	3.736 (3)	125

Symmetry code: (i) .