1,6-Bis(diphenyl-arsino)hexa-ne.

The title diphenyl-arsino compound, C(30)H(32)As(2) or Ph(2)As(CH(2))(6)AsPh(2), lies about a crystallographic inversion centre located at the mid-point of the central Csp(3)-Csp(3) bond of the methyl-ene chain. The two benzene rings bonded to As are inclined to one another at a dihedral angle of 75.98 (8)°. In the crystal structure, weak inter-molecular C-H⋯π inter-actions stack the mol-ecules down the b axis.

Related literature

For general background to and applications of diphenyl­arsino derivatives, see: Hill et al. (1983 ▶); Song et al. (2005 ▶). For the preparation of the title compound, see: Aguiar & Archibald (1967 ▶); Burfield et al. (1977 ▶, 1978 ▶); Tzschach & Lange (1962 ▶). For closely related structures, see: Hill et al. (2001 ▶); Shawkataly et al. (2005 ▶). For information on the Cambridge Structural Database, see: Allen (2002 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C30H32As2

M = 542.40

Monoclinic,

a = 12.3774 (2) Å

b = 5.7145 (1) Å

c = 18.1263 (3) Å

β = 101.076 (1)°

V = 1258.20 (4) Å3

Z = 2

Mo Kα radiation

μ = 2.67 mm−1

T = 100 K

0.44 × 0.29 × 0.03 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.384, T max = 0.919

24043 measured reflections

5572 independent reflections

4144 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.084

S = 1.03

5572 reflections

209 parameters

All H-atom parameters refined

Δρmax = 0.58 e Å−3

Δρmin = −0.47 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809036757/sj2648sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809036757/sj2648Isup2.hkl

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

C30H32As2	F(000) = 556
Mr = 542.40	Dx = 1.432 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5477 reflections
a = 12.3774 (2) Å	θ = 3.1–32.2°
b = 5.7145 (1) Å	µ = 2.67 mm−1
c = 18.1263 (3) Å	T = 100 K
β = 101.076 (1)°	Plate, colourless
V = 1258.20 (4) Å3	0.44 × 0.29 × 0.03 mm
Z = 2

Bruker SMART APEXII CCD area-detector diffractometer	5572 independent reflections
Radiation source: fine-focus sealed tube	4144 reflections with I > 2σ(I)
graphite	Rint = 0.052
φ and ω scans	θmax = 35.1°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −19→20
Tmin = 0.384, Tmax = 0.919	k = −9→8
24043 measured reflections	l = −29→26

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.084	All H-atom parameters refined
S = 1.03	w = 1/[σ2(Fo2) + (0.0344P)2 + 0.3375P] where P = (Fo2 + 2Fc2)/3
5572 reflections	(Δ/σ)max = 0.001
209 parameters	Δρmax = 0.58 e Å−3
0 restraints	Δρmin = −0.47 e Å−3

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

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
As1	0.351354 (13)	0.98218 (3)	0.284872 (8)	0.01668 (5)
C1	0.29473 (13)	0.8690 (3)	0.18275 (8)	0.0183 (3)
C2	0.32226 (14)	0.6566 (3)	0.15347 (9)	0.0226 (3)
C3	0.27896 (15)	0.5965 (4)	0.07878 (10)	0.0264 (4)
C4	0.20763 (15)	0.7469 (4)	0.03339 (10)	0.0299 (4)
C5	0.17979 (17)	0.9578 (4)	0.06212 (10)	0.0313 (4)
C6	0.22374 (16)	1.0190 (3)	0.13583 (10)	0.0257 (3)
C7	0.20975 (13)	0.9750 (3)	0.31860 (8)	0.0165 (3)
C8	0.13587 (13)	0.7891 (3)	0.30118 (9)	0.0192 (3)
C9	0.03431 (14)	0.7930 (3)	0.32299 (9)	0.0224 (3)
C10	0.00492 (14)	0.9838 (3)	0.36256 (9)	0.0225 (3)
C11	0.07749 (14)	1.1692 (3)	0.38019 (9)	0.0235 (3)
C12	0.17944 (14)	1.1653 (3)	0.35879 (9)	0.0208 (3)
C13	0.41464 (14)	0.6910 (3)	0.33284 (9)	0.0195 (3)
C14	0.43828 (15)	0.7124 (3)	0.41818 (9)	0.0218 (3)
C15	0.48951 (15)	0.4927 (3)	0.45720 (9)	0.0234 (3)
H2	0.3700 (19)	0.552 (4)	0.1820 (12)	0.026 (6)*
H3	0.303 (2)	0.458 (4)	0.0593 (13)	0.031 (6)*
H4	0.1799 (19)	0.704 (4)	−0.0149 (13)	0.040 (6)*
H5	0.128 (2)	1.066 (5)	0.0299 (15)	0.048 (7)*
H6	0.2055 (18)	1.172 (4)	0.1569 (12)	0.034 (6)*
H8	0.1550 (16)	0.654 (4)	0.2729 (11)	0.026 (5)*
H9	−0.0121 (17)	0.669 (4)	0.3102 (12)	0.033 (6)*
H10	−0.063 (2)	0.989 (4)	0.3763 (14)	0.033 (7)*
H11	0.0573 (18)	1.300 (4)	0.4072 (12)	0.036 (6)*
H12	0.2278 (16)	1.291 (4)	0.3710 (11)	0.024 (5)*
H13A	0.4768 (18)	0.668 (4)	0.3164 (12)	0.033 (6)*
H13B	0.364 (2)	0.570 (4)	0.3189 (13)	0.032 (6)*
H14A	0.370 (2)	0.752 (5)	0.4355 (13)	0.043 (7)*
H14B	0.4872 (17)	0.844 (4)	0.4344 (11)	0.026 (5)*
H15A	0.4390 (19)	0.362 (5)	0.4414 (13)	0.037 (6)*
H15B	0.556 (2)	0.465 (4)	0.4373 (14)	0.032 (6)*

	U11	U22	U33	U12	U13	U23
As1	0.01574 (8)	0.01865 (8)	0.01533 (7)	−0.00094 (6)	0.00222 (5)	0.00114 (6)
C1	0.0172 (6)	0.0221 (7)	0.0160 (6)	−0.0017 (6)	0.0044 (5)	0.0026 (5)
C2	0.0218 (7)	0.0269 (8)	0.0194 (7)	0.0002 (7)	0.0050 (6)	0.0007 (6)
C3	0.0285 (9)	0.0296 (9)	0.0225 (8)	−0.0069 (7)	0.0087 (7)	−0.0053 (7)
C4	0.0283 (9)	0.0462 (11)	0.0147 (7)	−0.0115 (8)	0.0028 (6)	−0.0013 (7)
C5	0.0299 (9)	0.0430 (11)	0.0185 (7)	0.0012 (8)	−0.0011 (7)	0.0079 (7)
C6	0.0269 (8)	0.0299 (9)	0.0195 (7)	0.0042 (7)	0.0027 (6)	0.0046 (6)
C7	0.0169 (6)	0.0182 (7)	0.0137 (6)	0.0008 (5)	0.0014 (5)	0.0017 (5)
C8	0.0195 (7)	0.0187 (7)	0.0188 (7)	0.0003 (6)	0.0022 (5)	−0.0016 (5)
C9	0.0204 (7)	0.0243 (8)	0.0217 (7)	−0.0025 (6)	0.0018 (6)	−0.0010 (6)
C10	0.0173 (7)	0.0303 (9)	0.0198 (7)	0.0033 (6)	0.0035 (6)	0.0008 (6)
C11	0.0258 (8)	0.0243 (8)	0.0200 (7)	0.0046 (7)	0.0034 (6)	−0.0030 (6)
C12	0.0219 (7)	0.0195 (7)	0.0200 (7)	−0.0005 (6)	0.0013 (6)	−0.0013 (6)
C13	0.0186 (7)	0.0239 (8)	0.0156 (6)	0.0047 (6)	0.0022 (5)	0.0022 (6)
C14	0.0235 (8)	0.0263 (8)	0.0149 (6)	0.0071 (7)	0.0016 (6)	0.0015 (6)
C15	0.0250 (8)	0.0283 (9)	0.0154 (6)	0.0096 (7)	0.0003 (6)	0.0008 (6)

As1—C1	1.9590 (15)	C8—H8	0.98 (2)
As1—C7	1.9644 (16)	C9—C10	1.391 (2)
As1—C13	1.9688 (16)	C9—H9	0.91 (2)
C1—C2	1.393 (2)	C10—C11	1.386 (3)
C1—C6	1.394 (2)	C10—H10	0.93 (3)
C2—C3	1.400 (2)	C11—C12	1.390 (2)
C2—H2	0.93 (2)	C11—H11	0.95 (2)
C3—C4	1.384 (3)	C12—H12	0.94 (2)
C3—H3	0.94 (2)	C13—C14	1.523 (2)
C4—C5	1.383 (3)	C13—H13A	0.89 (2)
C4—H4	0.91 (2)	C13—H13B	0.93 (3)
C5—C6	1.387 (3)	C14—C15	1.519 (2)
C5—H5	0.99 (3)	C14—H14A	0.98 (2)
C6—H6	0.99 (2)	C14—H14B	0.98 (2)
C7—C8	1.398 (2)	C15—C15i	1.525 (3)
C7—C12	1.399 (2)	C15—H15A	0.98 (3)
C8—C9	1.388 (2)	C15—H15B	0.97 (3)
C1—As1—C7	96.24 (6)	C10—C9—H9	121.6 (14)
C1—As1—C13	100.26 (7)	C11—C10—C9	119.72 (16)
C7—As1—C13	98.51 (7)	C11—C10—H10	119.9 (13)
C2—C1—C6	118.37 (15)	C9—C10—H10	120.4 (14)
C2—C1—As1	125.33 (12)	C10—C11—C12	120.41 (16)
C6—C1—As1	116.28 (13)	C10—C11—H11	119.8 (14)
C1—C2—C3	120.38 (17)	C12—C11—H11	119.8 (14)
C1—C2—H2	121.8 (14)	C11—C12—C7	120.44 (16)
C3—C2—H2	117.8 (14)	C11—C12—H12	119.7 (12)
C4—C3—C2	120.32 (18)	C7—C12—H12	119.9 (13)
C4—C3—H3	120.8 (14)	C14—C13—As1	111.29 (11)
C2—C3—H3	118.7 (15)	C14—C13—H13A	110.1 (14)
C5—C4—C3	119.60 (16)	As1—C13—H13A	105.9 (15)
C5—C4—H4	121.5 (16)	C14—C13—H13B	108.8 (15)
C3—C4—H4	118.9 (16)	As1—C13—H13B	108.4 (15)
C4—C5—C6	120.16 (18)	H13A—C13—H13B	112 (2)
C4—C5—H5	119.9 (16)	C15—C14—C13	112.84 (14)
C6—C5—H5	119.9 (16)	C15—C14—H14A	110.5 (15)
C5—C6—C1	121.15 (18)	C13—C14—H14A	109.6 (13)
C5—C6—H6	121.0 (13)	C15—C14—H14B	108.6 (12)
C1—C6—H6	117.9 (12)	C13—C14—H14B	110.8 (12)
C8—C7—C12	118.61 (15)	H14A—C14—H14B	104.2 (19)
C8—C7—As1	121.98 (12)	C14—C15—C15i	113.73 (18)
C12—C7—As1	119.36 (12)	C14—C15—H15A	107.9 (14)
C9—C8—C7	120.81 (15)	C15i—C15—H15A	108.3 (14)
C9—C8—H8	119.0 (12)	C14—C15—H15B	105.7 (14)
C7—C8—H8	120.2 (12)	C15i—C15—H15B	113.3 (15)
C8—C9—C10	120.01 (16)	H15A—C15—H15B	107.6 (19)
C8—C9—H9	118.4 (14)
C7—As1—C1—C2	−114.45 (14)	C1—As1—C7—C12	−134.94 (13)
C13—As1—C1—C2	−14.60 (15)	C13—As1—C7—C12	123.67 (13)
C7—As1—C1—C6	67.51 (14)	C12—C7—C8—C9	0.2 (2)
C13—As1—C1—C6	167.36 (13)	As1—C7—C8—C9	−177.24 (12)
C6—C1—C2—C3	−0.2 (2)	C7—C8—C9—C10	0.1 (2)
As1—C1—C2—C3	−178.21 (13)	C8—C9—C10—C11	−0.1 (2)
C1—C2—C3—C4	−0.5 (3)	C9—C10—C11—C12	−0.2 (3)
C2—C3—C4—C5	0.4 (3)	C10—C11—C12—C7	0.6 (2)
C3—C4—C5—C6	0.5 (3)	C8—C7—C12—C11	−0.6 (2)
C4—C5—C6—C1	−1.2 (3)	As1—C7—C12—C11	176.96 (12)
C2—C1—C6—C5	1.0 (3)	C1—As1—C13—C14	−165.02 (12)
As1—C1—C6—C5	179.24 (15)	C7—As1—C13—C14	−67.05 (13)
C1—As1—C7—C8	42.50 (13)	As1—C13—C14—C15	−178.78 (13)
C13—As1—C7—C8	−58.90 (13)	C13—C14—C15—C15i	−178.14 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15B···Cg1ii	0.97 (3)	2.81 (3)	3.776 (2)	169.9 (18)
C4—H4···Cg2iii	0.91 (2)	2.80 (2)	3.708 (2)	173.2 (19)
C9—H9···Cg2iv	0.91 (2)	2.97 (2)	3.617 (2)	129.5 (16)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15B⋯Cg1i	0.97 (3)	2.81 (3)	3.776 (2)	169.9 (18)
C4—H4⋯Cg2ii	0.91 (2)	2.80 (2)	3.708 (2)	173.2 (19)
C9—H9⋯Cg2iii	0.91 (2)	2.97 (2)	3.617 (2)	129.5 (16)

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 and Cg2 are the centroids of the C1–C6 and C7–C12 benzene rings, respectively.