Bis[bis­(2-methyl­phen­yl)phosphan­yl]methane

Shawkataly, O. bin; Khan, I.A.; Hafiz Malik, H.A.; Yeap, C.S.; Fun, H.-K.

doi:10.1107/S1600536810054279

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o289

doi:10.1107/S1600536810054279

Open

access

Bis[bis(2-methylphenyl)phosphanyl]methane

Omar bin Shawkataly,^a ^*‡ Imthyaz Ahmed Khan,^a § H. A. Hafiz Malik,^a Chin Sing Yeap ^b ¶ and Hoong-Kun Fun ^b ‡‡

^aChemical Sciences Programme, School of Distance Education, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: omarsa@usm.my

(Received 20 December 2010; accepted 25 December 2010; online 8 January 2011)

In the title compound, C₂₉H₃₀P₂, the dihedral angles between the two substituted benzene rings to the same P atom are 88.39 (7) and 83.88 (9)°. In the crystal, molecules are arranged into columns and stacked down the b axis. Weak intermolecular C—H⋯π interactions stabilize the crystal structure.

Related literature

For related structures, see: Filby et al. (2006 ); Lumbreras et al. (2010 ). For the synthesis of bis(di-o-tolylphosphino)methane, see: Filby et al. (2006). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₉H₃₀P₂
M_r = 440.47
Monoclinic, P 2₁ /c
a = 8.2991 (5) Å
b = 7.4050 (5) Å
c = 40.782 (3) Å
β = 95.189 (1)°
V = 2496.0 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 100 K
0.43 × 0.42 × 0.10 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.924, T_max = 0.981
27134 measured reflections
10066 independent reflections
8035 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.137
S = 1.07
10066 reflections
284 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C7–C12 and C20–C25 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯Cg1ⁱ	0.93	2.83	3.7325 (18)	164
C28—H28A⋯Cg2ⁱⁱ	0.96	2.76	3.6929 (18)	165
Symmetry codes: (i) -x, -y+1, -z; (ii) x, y-1, z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; 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 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810054279/ng5093sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810054279/ng5093Isup2.hkl

checkCIF report

Comment top

Diphosphines are an important class of ligands that finds widespread use in transition metal chemistry and catalysis. A subclass of these is small bite-angle diphosphines in which the two phosphorus centers are separated only by a single atom linker unit. The small bite-angle ligand bis(di-o-tolylphosphino)methane is used in the synthesis of palladium complexes (Filby et al., 2006; Lumbreras et al., 2010).

The dihedral angles between the two substituted benzene rings (C1–C6/C7–C12 and C14–C19/C20–C25) to the same phosphine atom (P1 and P2) are 88.39 (7) and 83.88 (9)° respectively (Fig. 1). In the crystal packing, the molecules are arranged into columns and stacked down b axis. (Fig. 2). Weak intermolecular C—H···π interactions (Table 1) further stabilize the crystal structure.

Related literature top

For related structures, see: Filby et al. (2006); Lumbreras et al. (2010). For the synthesis of bis(di-o-tolylphosphino)methane, see: Filby et al. (2006). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

All manipulations were performed under a dry oxygen-free nitrogen atmosphere using standard Schlenk techniques. All solvents were dried over sodium and distilled from sodium benzophenone ketyl under dry oxygen free nitrogen. Bis(di-o-tolylphosphino)methane was prepared by reported procedure (Filby et al., 2006). Crystals suitable for X-ray diffraction were grown by slow solvent / solvent diffusion of CH₃OH into CHCl₃.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with 50% probability ellipsoids for non-H atoms.
	Fig. 2. The crystal packing of the title compound, viewed down the b axis, showing the molecules stacked down the b axis.

Bis[bis(2-methylphenyl)phosphanyl]methane top

Crystal data top

C₂₉H₃₀P₂	F(000) = 936
M_r = 440.47	D_x = 1.172 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6549 reflections
a = 8.2991 (5) Å	θ = 4.6–33.8°
b = 7.4050 (5) Å	µ = 0.19 mm⁻¹
c = 40.782 (3) Å	T = 100 K
β = 95.189 (1)°	Plate, colourless
V = 2496.0 (3) Å³	0.43 × 0.42 × 0.10 mm
Z = 4

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	10066 independent reflections
Radiation source: fine-focus sealed tube	8035 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
ϕ and ω scans	θ_max = 34.0°, θ_min = 4.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→12
T_min = 0.924, T_max = 0.981	k = −11→11
27134 measured reflections	l = −51→64

Refinement top

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.137	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0572P)² + 0.7579P] where P = (F_o² + 2F_c²)/3
10066 reflections	(Δ/σ)_max < 0.001
284 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₉H₃₀P₂	V = 2496.0 (3) Å³
M_r = 440.47	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.2991 (5) Å	µ = 0.19 mm⁻¹
b = 7.4050 (5) Å	T = 100 K
c = 40.782 (3) Å	0.43 × 0.42 × 0.10 mm
β = 95.189 (1)°

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	10066 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	8035 reflections with I > 2σ(I)
T_min = 0.924, T_max = 0.981	R_int = 0.041
27134 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.137	H-atom parameters constrained
S = 1.07	Δρ_max = 0.36 e Å⁻³
10066 reflections	Δρ_min = −0.23 e Å⁻³
284 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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

	x	y	z	U_iso*/U_eq
P1	0.18382 (3)	0.27891 (4)	0.086016 (7)	0.01724 (7)
P2	0.16377 (4)	0.13495 (5)	0.154290 (8)	0.02634 (8)
C1	0.23722 (13)	0.48860 (15)	0.06551 (3)	0.01841 (19)
C2	0.29605 (15)	0.64220 (16)	0.08257 (3)	0.0230 (2)
H2A	0.2991	0.6448	0.1054	0.028*
C3	0.35022 (16)	0.79130 (18)	0.06591 (4)	0.0285 (3)
H3A	0.3887	0.8928	0.0776	0.034*
C4	0.34666 (19)	0.7880 (2)	0.03197 (4)	0.0342 (3)
H4A	0.3834	0.8870	0.0207	0.041*
C5	0.2885 (2)	0.6374 (2)	0.01471 (4)	0.0361 (3)
H5A	0.2860	0.6367	−0.0081	0.043*
C6	0.23309 (16)	0.48582 (19)	0.03092 (3)	0.0267 (2)
C7	−0.03857 (13)	0.28696 (17)	0.08034 (3)	0.0217 (2)
C8	−0.11985 (17)	0.4501 (2)	0.08482 (4)	0.0320 (3)
H8A	−0.0605	0.5535	0.0907	0.038*
C9	−0.28755 (19)	0.4594 (3)	0.08063 (5)	0.0438 (4)
H9A	−0.3406	0.5678	0.0838	0.053*
C10	−0.37401 (17)	0.3062 (3)	0.07174 (5)	0.0467 (5)
H10A	−0.4864	0.3115	0.0689	0.056*
C11	−0.29677 (17)	0.1445 (3)	0.06704 (4)	0.0399 (4)
H11A	−0.3579	0.0428	0.0608	0.048*
C12	−0.12682 (15)	0.13087 (19)	0.07148 (3)	0.0273 (2)
C13	0.21569 (16)	0.33585 (17)	0.13027 (3)	0.0245 (2)
H13A	0.1475	0.4370	0.1352	0.029*
H13B	0.3277	0.3695	0.1360	0.029*
C14	0.34812 (18)	−0.00360 (18)	0.15611 (3)	0.0282 (3)
C15	0.48803 (19)	0.0451 (2)	0.14168 (4)	0.0352 (3)
H15A	0.4921	0.1566	0.1313	0.042*
C16	0.6214 (2)	−0.0687 (3)	0.14243 (5)	0.0464 (4)
H16A	0.7136	−0.0331	0.1328	0.056*
C17	0.6162 (3)	−0.2354 (3)	0.15766 (5)	0.0492 (5)
H17A	0.7045	−0.3128	0.1581	0.059*
C18	0.4799 (3)	−0.2860 (2)	0.17213 (4)	0.0451 (4)
H18A	0.4779	−0.3978	0.1825	0.054*
C19	0.3439 (2)	−0.17399 (19)	0.17171 (4)	0.0344 (3)
C20	0.1778 (2)	0.23619 (19)	0.19566 (4)	0.0360 (3)
C21	0.3219 (3)	0.2361 (2)	0.21606 (4)	0.0495 (5)
H21A	0.4140	0.1830	0.2089	0.059*
C22	0.3289 (4)	0.3153 (3)	0.24723 (5)	0.0738 (8)
H22A	0.4254	0.3143	0.2607	0.089*
C23	0.1940 (5)	0.3944 (3)	0.25798 (5)	0.0817 (10)
H23A	0.1989	0.4464	0.2788	0.098*
C24	0.0516 (4)	0.3970 (2)	0.23803 (6)	0.0698 (8)
H24A	−0.0386	0.4528	0.2455	0.084*
C25	0.0383 (3)	0.3179 (2)	0.20667 (5)	0.0476 (5)
C26	0.1731 (2)	0.3240 (2)	0.01096 (4)	0.0415 (4)
H26A	0.2340	0.2192	0.0184	0.062*
H26B	0.1865	0.3450	−0.0119	0.062*
H26C	0.0607	0.3047	0.0136	0.062*
C27	−0.04883 (19)	−0.0484 (2)	0.06702 (5)	0.0401 (4)
H27A	0.0148	−0.0813	0.0869	0.060*
H27B	0.0197	−0.0410	0.0493	0.060*
H27C	−0.1309	−0.1380	0.0619	0.060*
C28	0.1983 (3)	−0.2342 (2)	0.18810 (5)	0.0504 (5)
H28A	0.2161	−0.3540	0.1967	0.076*
H28B	0.1051	−0.2339	0.1723	0.076*
H28C	0.1806	−0.1532	0.2058	0.076*
C29	−0.1195 (3)	0.3245 (3)	0.18557 (7)	0.0634 (6)
H29A	−0.2006	0.3789	0.1977	0.095*
H29B	−0.1521	0.2041	0.1793	0.095*
H29C	−0.1067	0.3948	0.1662	0.095*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.01554 (12)	0.01656 (13)	0.01936 (13)	0.00128 (9)	0.00012 (8)	0.00058 (9)
P2	0.03679 (18)	0.02088 (15)	0.02149 (15)	−0.00247 (12)	0.00350 (12)	0.00215 (11)
C1	0.0162 (4)	0.0182 (5)	0.0208 (5)	0.0014 (4)	0.0018 (3)	0.0014 (4)
C2	0.0241 (5)	0.0201 (5)	0.0250 (5)	0.0002 (4)	0.0038 (4)	−0.0015 (4)
C3	0.0270 (6)	0.0205 (5)	0.0387 (7)	−0.0026 (5)	0.0059 (5)	0.0002 (5)
C4	0.0359 (7)	0.0275 (6)	0.0403 (8)	−0.0046 (5)	0.0103 (6)	0.0096 (6)
C5	0.0486 (8)	0.0351 (7)	0.0249 (6)	−0.0052 (6)	0.0059 (6)	0.0076 (5)
C6	0.0310 (6)	0.0281 (6)	0.0209 (5)	−0.0033 (5)	0.0013 (4)	0.0020 (4)
C7	0.0164 (4)	0.0253 (5)	0.0237 (5)	0.0036 (4)	0.0039 (4)	0.0058 (4)
C8	0.0289 (6)	0.0316 (7)	0.0370 (7)	0.0123 (5)	0.0106 (5)	0.0081 (5)
C9	0.0287 (7)	0.0541 (10)	0.0511 (10)	0.0221 (7)	0.0167 (6)	0.0190 (8)
C10	0.0181 (6)	0.0732 (12)	0.0503 (10)	0.0098 (7)	0.0111 (6)	0.0275 (9)
C11	0.0209 (6)	0.0554 (10)	0.0430 (8)	−0.0091 (6)	0.0004 (5)	0.0179 (7)
C12	0.0188 (5)	0.0326 (6)	0.0299 (6)	−0.0043 (5)	0.0000 (4)	0.0079 (5)
C13	0.0326 (6)	0.0202 (5)	0.0204 (5)	−0.0005 (4)	0.0000 (4)	0.0021 (4)
C14	0.0431 (7)	0.0218 (5)	0.0191 (5)	0.0004 (5)	−0.0008 (5)	0.0007 (4)
C15	0.0389 (7)	0.0363 (7)	0.0293 (7)	0.0043 (6)	−0.0023 (5)	0.0083 (6)
C16	0.0424 (8)	0.0562 (11)	0.0395 (9)	0.0122 (8)	−0.0021 (7)	0.0064 (8)
C17	0.0603 (11)	0.0460 (10)	0.0387 (9)	0.0228 (9)	−0.0105 (8)	−0.0021 (7)
C18	0.0782 (13)	0.0264 (7)	0.0279 (7)	0.0123 (8)	−0.0111 (7)	−0.0009 (5)
C19	0.0600 (9)	0.0202 (5)	0.0222 (6)	0.0001 (6)	−0.0007 (6)	−0.0011 (4)
C20	0.0657 (10)	0.0208 (6)	0.0225 (6)	−0.0005 (6)	0.0102 (6)	0.0035 (5)
C21	0.0885 (14)	0.0334 (8)	0.0243 (7)	0.0016 (8)	−0.0067 (8)	−0.0027 (6)
C22	0.147 (3)	0.0442 (10)	0.0264 (8)	−0.0001 (13)	−0.0151 (11)	−0.0057 (8)
C23	0.183 (3)	0.0383 (10)	0.0264 (8)	0.0056 (14)	0.0223 (14)	−0.0045 (8)
C24	0.144 (2)	0.0280 (8)	0.0453 (11)	0.0098 (11)	0.0530 (14)	0.0054 (7)
C25	0.0845 (14)	0.0230 (6)	0.0401 (9)	0.0046 (8)	0.0322 (9)	0.0090 (6)
C26	0.0633 (10)	0.0380 (8)	0.0220 (6)	−0.0137 (7)	−0.0022 (6)	−0.0033 (6)
C27	0.0320 (7)	0.0270 (7)	0.0599 (11)	−0.0073 (6)	−0.0030 (6)	−0.0035 (7)
C28	0.0842 (14)	0.0236 (7)	0.0458 (10)	−0.0068 (8)	0.0188 (9)	0.0061 (6)
C29	0.0702 (14)	0.0477 (11)	0.0785 (16)	0.0154 (10)	0.0405 (12)	0.0136 (10)

Geometric parameters (Å, º) top

P1—C1	1.8368 (12)	C15—C16	1.389 (2)
P1—C7	1.8402 (11)	C15—H15A	0.9300
P1—C13	1.8491 (13)	C16—C17	1.384 (3)
P2—C14	1.8380 (15)	C16—H16A	0.9300
P2—C20	1.8404 (15)	C17—C18	1.375 (3)
P2—C13	1.8532 (13)	C17—H17A	0.9300
C1—C2	1.3981 (17)	C18—C19	1.399 (2)
C1—C6	1.4080 (17)	C18—H18A	0.9300
C2—C3	1.3922 (18)	C19—C28	1.500 (3)
C2—H2A	0.9300	C20—C21	1.394 (3)
C3—C4	1.382 (2)	C20—C25	1.415 (3)
C3—H3A	0.9300	C21—C22	1.396 (3)
C4—C5	1.382 (2)	C21—H21A	0.9300
C4—H4A	0.9300	C22—C23	1.371 (4)
C5—C6	1.4013 (19)	C22—H22A	0.9300
C5—H5A	0.9300	C23—C24	1.373 (4)
C6—C26	1.508 (2)	C23—H23A	0.9300
C7—C12	1.3982 (19)	C24—C25	1.402 (3)
C7—C8	1.4037 (18)	C24—H24A	0.9300
C8—C9	1.388 (2)	C25—C29	1.502 (4)
C8—H8A	0.9300	C26—H26A	0.9600
C9—C10	1.374 (3)	C26—H26B	0.9600
C9—H9A	0.9300	C26—H26C	0.9600
C10—C11	1.380 (3)	C27—H27A	0.9600
C10—H10A	0.9300	C27—H27B	0.9600
C11—C12	1.4093 (18)	C27—H27C	0.9600
C11—H11A	0.9300	C28—H28A	0.9600
C12—C27	1.495 (2)	C28—H28B	0.9600
C13—H13A	0.9700	C28—H28C	0.9600
C13—H13B	0.9700	C29—H29A	0.9600
C14—C15	1.396 (2)	C29—H29B	0.9600
C14—C19	1.4150 (19)	C29—H29C	0.9600

C1—P1—C7	101.29 (5)	C17—C16—C15	119.57 (18)
C1—P1—C13	103.45 (5)	C17—C16—H16A	120.2
C7—P1—C13	99.71 (6)	C15—C16—H16A	120.2
C14—P2—C20	101.95 (7)	C18—C17—C16	119.76 (17)
C14—P2—C13	103.71 (6)	C18—C17—H17A	120.1
C20—P2—C13	99.16 (6)	C16—C17—H17A	120.1
C2—C1—C6	119.09 (11)	C17—C18—C19	121.80 (16)
C2—C1—P1	123.29 (9)	C17—C18—H18A	119.1
C6—C1—P1	117.30 (9)	C19—C18—H18A	119.1
C3—C2—C1	121.06 (12)	C18—C19—C14	118.78 (16)
C3—C2—H2A	119.5	C18—C19—C28	119.95 (15)
C1—C2—H2A	119.5	C14—C19—C28	121.27 (15)
C4—C3—C2	119.74 (13)	C21—C20—C25	119.57 (16)
C4—C3—H3A	120.1	C21—C20—P2	121.78 (14)
C2—C3—H3A	120.1	C25—C20—P2	118.65 (15)
C5—C4—C3	119.95 (13)	C20—C21—C22	120.4 (2)
C5—C4—H4A	120.0	C20—C21—H21A	119.8
C3—C4—H4A	120.0	C22—C21—H21A	119.8
C4—C5—C6	121.37 (14)	C23—C22—C21	120.2 (3)
C4—C5—H5A	119.3	C23—C22—H22A	119.9
C6—C5—H5A	119.3	C21—C22—H22A	119.9
C5—C6—C1	118.79 (12)	C22—C23—C24	120.04 (19)
C5—C6—C26	119.24 (13)	C22—C23—H23A	120.0
C1—C6—C26	121.97 (12)	C24—C23—H23A	120.0
C12—C7—C8	119.90 (12)	C23—C24—C25	121.8 (2)
C12—C7—P1	120.11 (9)	C23—C24—H24A	119.1
C8—C7—P1	119.99 (10)	C25—C24—H24A	119.1
C9—C8—C7	120.98 (16)	C24—C25—C20	118.0 (2)
C9—C8—H8A	119.5	C24—C25—C29	120.1 (2)
C7—C8—H8A	119.5	C20—C25—C29	121.89 (17)
C10—C9—C8	119.04 (15)	C6—C26—H26A	109.5
C10—C9—H9A	120.5	C6—C26—H26B	109.5
C8—C9—H9A	120.5	H26A—C26—H26B	109.5
C9—C10—C11	121.03 (13)	C6—C26—H26C	109.5
C9—C10—H10A	119.5	H26A—C26—H26C	109.5
C11—C10—H10A	119.5	H26B—C26—H26C	109.5
C10—C11—C12	121.08 (16)	C12—C27—H27A	109.5
C10—C11—H11A	119.5	C12—C27—H27B	109.5
C12—C11—H11A	119.5	H27A—C27—H27B	109.5
C7—C12—C11	117.96 (14)	C12—C27—H27C	109.5
C7—C12—C27	122.89 (11)	H27A—C27—H27C	109.5
C11—C12—C27	119.14 (14)	H27B—C27—H27C	109.5
P1—C13—P2	108.26 (7)	C19—C28—H28A	109.5
P1—C13—H13A	110.0	C19—C28—H28B	109.5
P2—C13—H13A	110.0	H28A—C28—H28B	109.5
P1—C13—H13B	110.0	C19—C28—H28C	109.5
P2—C13—H13B	110.0	H28A—C28—H28C	109.5
H13A—C13—H13B	108.4	H28B—C28—H28C	109.5
C15—C14—C19	118.38 (14)	C25—C29—H29A	109.5
C15—C14—P2	124.06 (11)	C25—C29—H29B	109.5
C19—C14—P2	117.48 (12)	H29A—C29—H29B	109.5
C16—C15—C14	121.71 (15)	C25—C29—H29C	109.5
C16—C15—H15A	119.1	H29A—C29—H29C	109.5
C14—C15—H15A	119.1	H29B—C29—H29C	109.5

C7—P1—C1—C2	106.29 (10)	C14—P2—C13—P1	82.71 (7)
C13—P1—C1—C2	3.31 (11)	C20—P2—C13—P1	−172.51 (8)
C7—P1—C1—C6	−80.18 (10)	C20—P2—C14—C15	−102.79 (13)
C13—P1—C1—C6	176.84 (9)	C13—P2—C14—C15	−0.14 (14)
C6—C1—C2—C3	−0.01 (18)	C20—P2—C14—C19	80.55 (12)
P1—C1—C2—C3	173.42 (10)	C13—P2—C14—C19	−176.80 (10)
C1—C2—C3—C4	−0.3 (2)	C19—C14—C15—C16	−0.2 (2)
C2—C3—C4—C5	0.4 (2)	P2—C14—C15—C16	−176.83 (13)
C3—C4—C5—C6	−0.3 (2)	C14—C15—C16—C17	0.4 (3)
C4—C5—C6—C1	0.1 (2)	C15—C16—C17—C18	−0.6 (3)
C4—C5—C6—C26	−179.09 (16)	C16—C17—C18—C19	0.6 (3)
C2—C1—C6—C5	0.10 (18)	C17—C18—C19—C14	−0.4 (2)
P1—C1—C6—C5	−173.72 (11)	C17—C18—C19—C28	−179.46 (17)
C2—C1—C6—C26	179.24 (14)	C15—C14—C19—C18	0.2 (2)
P1—C1—C6—C26	5.43 (18)	P2—C14—C19—C18	177.07 (11)
C1—P1—C7—C12	137.48 (10)	C15—C14—C19—C28	179.22 (15)
C13—P1—C7—C12	−116.57 (11)	P2—C14—C19—C28	−3.92 (19)
C1—P1—C7—C8	−42.34 (12)	C14—P2—C20—C21	15.95 (15)
C13—P1—C7—C8	63.60 (11)	C13—P2—C20—C21	−90.27 (14)
C12—C7—C8—C9	0.1 (2)	C14—P2—C20—C25	−164.84 (11)
P1—C7—C8—C9	179.92 (12)	C13—P2—C20—C25	88.93 (12)
C7—C8—C9—C10	−0.5 (2)	C25—C20—C21—C22	0.3 (3)
C8—C9—C10—C11	0.1 (3)	P2—C20—C21—C22	179.50 (15)
C9—C10—C11—C12	0.6 (3)	C20—C21—C22—C23	−0.2 (3)
C8—C7—C12—C11	0.59 (19)	C21—C22—C23—C24	−0.4 (4)
P1—C7—C12—C11	−179.24 (11)	C22—C23—C24—C25	0.9 (3)
C8—C7—C12—C27	−178.62 (14)	C23—C24—C25—C20	−0.9 (3)
P1—C7—C12—C27	1.55 (19)	C23—C24—C25—C29	−179.73 (19)
C10—C11—C12—C7	−0.9 (2)	C21—C20—C25—C24	0.2 (2)
C10—C11—C12—C27	178.31 (16)	P2—C20—C25—C24	−178.99 (12)
C1—P1—C13—P2	179.41 (6)	C21—C20—C25—C29	179.07 (16)
C7—P1—C13—P2	75.22 (7)	P2—C20—C25—C29	−0.1 (2)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C7–C12 and C20–C25 benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···Cg1ⁱ	0.93	2.83	3.7325 (18)	164
C28—H28A···Cg2ⁱⁱ	0.96	2.76	3.6929 (18)	165

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

Experimental details

Crystal data
Chemical formula	C₂₉H₃₀P₂
M_r	440.47
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	8.2991 (5), 7.4050 (5), 40.782 (3)
β (°)	95.189 (1)
V (Å³)	2496.0 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.43 × 0.42 × 0.10

Data collection
Diffractometer	Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.924, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	27134, 10066, 8035
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.787

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.137, 1.07
No. of reflections	10066
No. of parameters	284
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.23

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C7–C12 and C20–C25 benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···Cg1ⁱ	0.93	2.83	3.7325 (18)	164
C28—H28A···Cg2ⁱⁱ	0.96	2.76	3.6929 (18)	165

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

Footnotes

‡Thomson Reuters ResearcherID: B-6034-2009. On secondment to: Multimedia University, Melaka Campus, Jalan Ayer Keroh Lama, 74750 Melaka, Malaysia.

§Thomson Reuters ResearcherID: E-2833-2010. Current address: Department of Chemistry, Gokhale Centenary College, Ankola 581 314, NK, Karnataka, India.

¶Thomson Reuters ResearcherID: A-5523-2009.

‡‡Thomson Reuters ResearcherID: A-3561-2009. Additional correspondence author, e-mail: hkfun@usm.my.

Acknowledgements

The authors would like to thank the Malaysian Government and Universiti Sains Malaysia (USM) for the Research grant 1001/PJJAUH/811115. IAK is grateful to USM for a Visiting Researcher position. HKF and CSY thank USM for the Research University Grant No. 1001/PFIZIK/811160.

References

Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Filby, M., Deeming, A. J., Hogarth, G. & Lee, M.-Y. (2006). Can. J. Chem. 84, 319–329. Web of Science CSD CrossRef CAS Google Scholar
Lumbreras, E. Jr, Sisler, E. M. & Shelby, Q. D. (2010). J. Organomet. Chem. 695, 201–205. CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o289

doi:10.1107/S1600536810054279

Open

access