Bis(μ-diethyl­phosphido-κ2P:P)bis­[bis(2,4,6-trimethyl­phen­yl)indium(III)]

Briand, G.G.; Decken, A.; Knackstedt, D.A.; Martin, C.D.

doi:10.1107/S1600536811042668

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page m1578

doi:10.1107/S1600536811042668

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Bis(μ-diethylphosphido-κ²P:P)bis[bis(2,4,6-trimethylphenyl)indium(III)]

Glen G. Briand,^a ^* Andreas Decken,^b Dane A. Knackstedt ^a and Caleb D. Martin ^a

^aDepartment of Chemistry and Biochemistry, Mount Allison University, 63C York Street, Sackville, New Brunswick, Canada E4L 1G8, and ^bDepartment of Chemistry, University of New Brunswick, Fredericton, New Brunswick, Canada E3B 5A3
^*Correspondence e-mail: gbriand@mta.ca

(Received 23 September 2011; accepted 14 October 2011; online 22 October 2011)

The title compound, [In₂(C₉H₁₁)₄(C₄H₁₀P)₂], contains a centrosymmetric In₂P₂ core with short intermolecular In—P bonds. This core has acute P—In—P and obtuse In—P—In bond angles compared with other [R₂InPR′₂]₂ analogues, due to the presence of the bulky aromatic substituents on the In atom and the non-sterically demanding ethyl substituents on the P atom.

Related literature

For related dimeric phosphanylindanes, see: Alcock et al. (1989 ); Wells et al. (1992 ); Aitchison et al. (1989 ); Beachley et al. (1987 , 1993 , 1995 , 2001 ); Culp et al. (1997 ); Malik et al. (1996 ); Thomas et al. (2002 ); Wells et al. (1993 ); von Hanisch (2001 ). For related trimeric phosphanylindanes, see: Burns et al. (1994 ); Werner & Neumüller (1996 ); Banks et al. (1991 ).

Experimental

Crystal data

[In₂(C₉H₁₁)₄(C₄H₁₀P)₂]
M_r = 884.53
Monoclinic, C 2/c
a = 22.323 (4) Å
b = 15.494 (4) Å
c = 14.331 (3) Å
β = 120.618 (4)°
V = 4265.6 (17) Å³
Z = 4
Mo Kα radiation
μ = 1.18 mm⁻¹
T = 198 K
0.23 × 0.20 × 0.01 mm

Data collection

Bruker SMART1000/P4 diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a ) T_min = 0.777, T_max = 0.988
14538 measured reflections
4771 independent reflections
3470 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.078
S = 1.09
4771 reflections
225 parameters
H-atom parameters constrained
Δρ_max = 0.65 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Data collection: SMART (Bruker, 1999 ); cell refinement: SMART; data reduction: SAINT (Bruker, 2006 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b); molecular graphics: DIAMOND (Brandenburg, 2011 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008b).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811042668/fj2456sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811042668/fj2456Isup2.hkl

checkCIF report

Comment top

Phosphanylindanes [R₂InPR'₂]_n form dimeric or trimeric structures in the solid state via intermolecular In—P coordinate bonding interactions (Beachley et al., 2001; Werner & Neumuller 1996). Dimeric structures feature distorted tetrahedral geometries at indium and phosphorus, and planar four-membered In₂P₂ ring cores. In—P bond distances within the ring are similar and differ by less than 0.05 Å in all reported structures (Wells et al., 1993). The structure of I (Fig. 1) shows a dimer in the solid state, with a characteristic In₂P₂ core and distorted tetrahedral geometries at the four coordinate indium and phosphorus centres. The In—P bond distances are similar [In—P = 2.6300 (12) Å, In—Pⁱ = 2.6364 (9) Å] and are in the range for previously reported dimeric phosphanylindanes [2.612 (1)–2.712 (1) Å] (Wells et al., 1993; Beachley et al., 1993). However, the ring P—In—Pⁱ bond angle [81.56 (3)°] is at the lower limit of the range of reported values for [R₂InPR'₂]₂ structures [81.80 (7)–87.53 (3)°] (Beachley et al., 1987; von Hanisch, 2001), and the In—P—Inⁱ bond angle [98.44 (3)°] is at the upper limit of reported values [92.47 (3)–98.20 (7)°] (von Hanisch, 2001; Beachley et al., 1987). The significant distortion of the In₂P₂ ring is likely a result of the bulky mesityl groups on indium, which affect a compression of the P—In—Pⁱ bond angles. Conversely, the non-bulky ethyl groups on phosphorus allows for expansion of the In—P—Inⁱ bond angles.

Related literature top

For related dimeric phosphanylindanes, see: Alcock et al. (1989); Wells et al. (1992); Aitchison et al. (1989); Beachley et al. (1987, 1993, 1995, 2001); Culp et al. (1997); Malik et al. (1996); Thomas et al. (2002); Wells et al. (1993); von Hanisch (2001). For related trimeric phosphanylindanes, see: Burns et al. (1994); Werner & Neumuller (1996); Banks et al. (1991).

Experimental top

Preparation of [(2,4,6-Me₃C₆H₂)₂InPEt₂]₂ (I). Trismesityl indium (0.520 g, 1.10 mmol) was added to a solution of diethyl phosphine (0.100 g, 1.10 mmol) in toluene (7.5 ml). The reaction mixture was stirred at 45°C for 72 h, after which time a white precipitate had formed. The precipitate was removed by filtration, dried in vacuo, and washed with toluene (2 × 5 ml) and hexane (3 ml) (yield 0.110 g, 22%). Mp: 188°C. Crystals of I were obtained by dissolving the product in dichloromethane and allowing the solution to sit at 23°C for 12 h.

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SMART (Bruker, 1999); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b); molecular graphics: DIAMOND (Brandenburg, 2011); software used to prepare material for publication: SHELXTL (Sheldrick, 2008b).

Figures top

Fig. 1. X-ray crystal structure of (I), with displacement ellipsoids drawn at the 50% probability level. H atoms have been omitted for clarity. Symmetry transformations used to generate equivalent atoms: (i) -x + 1/2, -y + 1/2, -z + 1. Selected bond distances (Å) and angles (°): In—P 2.6300 (12), In—Pⁱ 2.6364 (9), In—C1 2.190 (3), In—C10 2.215 (3), P—C19 1.866 (3), P—C21 1.856 (3), P—In—Pⁱ 81.56 (3), In—P—Inⁱ 98.44 (3), C1—In—C10 117.6 (1), C19—P—C21 104.4 (2).

Bis(µ-diethylphosphido-κ²P:P)bis[bis(2,4,6- trimethylphenyl)indium(III)] top

Crystal data top

[In₂(C₉H₁₁)₄(C₄H₁₀P)₂]	F(000) = 1824
M_r = 884.53	D_x = 1.377 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 6933 reflections
a = 22.323 (4) Å	θ = 2.7–28.1°
b = 15.494 (4) Å	µ = 1.18 mm⁻¹
c = 14.331 (3) Å	T = 198 K
β = 120.618 (4)°	Plate, colourless
V = 4265.6 (17) Å³	0.23 × 0.20 × 0.01 mm
Z = 4

Data collection top

Bruker SMART1000/P4 diffractometer	4771 independent reflections
Radiation source: fine-focus sealed tube, K760	3470 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
ϕ and ω scans	θ_max = 27.5°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)	h = −28→27
T_min = 0.777, T_max = 0.988	k = −19→19
14538 measured reflections	l = −18→18

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.078	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0318P)² + 1.4614P] where P = (F_o² + 2F_c²)/3
4771 reflections	(Δ/σ)_max = 0.001
225 parameters	Δρ_max = 0.65 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

[In₂(C₉H₁₁)₄(C₄H₁₀P)₂]	V = 4265.6 (17) Å³
M_r = 884.53	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 22.323 (4) Å	µ = 1.18 mm⁻¹
b = 15.494 (4) Å	T = 198 K
c = 14.331 (3) Å	0.23 × 0.20 × 0.01 mm
β = 120.618 (4)°

Data collection top

Bruker SMART1000/P4 diffractometer	4771 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)	3470 reflections with I > 2σ(I)
T_min = 0.777, T_max = 0.988	R_int = 0.038
14538 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.078	H-atom parameters constrained
S = 1.09	Δρ_max = 0.65 e Å⁻³
4771 reflections	Δρ_min = −0.34 e Å⁻³
225 parameters

Special details top

Experimental. Crystal decay was monitored by repeating the initial 50 frames at the end of the data collection and analyzing duplicate reflections

NMR data (p.p.m., CDCl₃): ¹H NMR, 0.88 (m, 6H, PCH₂CH₃), 1.83 (q, ³J(¹H-¹H) = 7 Hz, 4H, PCH₂CH₃), 2.24 (s, 6H, 2,4,6-Me₃C₆H₂), 2.33 (s, 12H, 2,4,6-Me₃C₆H₂), 6.78 (s, 4H, 2,4,6-Me₃C₆H₂); ¹³C{¹H}11.7 (PCH₂CH₃), 13.8 (PCH₂CH₃), 21.3 (s, 2,4,6-Me₃C₆H₂), 27.7 (s, 2,4,6-Me₃C₆H₂), 126.8 (s, 2,4,6-Me₃C₆H₂), 136.6 (s, 2,4,6-Me₃C₆H₂), 144.1 (s, 2,4,6-Me₃C₆H₂); ³¹P NMR, δ -44.63 (s). FT—IR: 538m, 607vw, 673w, 708w, 752w, 800w, 845m, 976w, 1030w, 1042w, 1090w, 1149vw, 1244w, 1259w, 1288w, 1402w, 1547w, 1595vw, 1712vw.

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
In1	0.231901 (11)	0.163644 (15)	0.585903 (16)	0.03479 (8)
P1	0.21902 (4)	0.33051 (6)	0.54684 (6)	0.03532 (19)
C1	0.14507 (16)	0.0724 (2)	0.5087 (2)	0.0355 (7)
C2	0.07490 (17)	0.0952 (2)	0.4400 (2)	0.0430 (8)
C3	0.02405 (18)	0.0319 (3)	0.3942 (3)	0.0504 (9)
H3	−0.0230	0.0488	0.3476	0.061*
C4	0.03963 (19)	−0.0550 (3)	0.4142 (3)	0.0512 (10)
C5	0.10908 (19)	−0.0781 (2)	0.4811 (3)	0.0466 (9)
H5	0.1210	−0.1375	0.4954	0.056*
C6	0.16177 (17)	−0.0161 (2)	0.5276 (2)	0.0381 (8)
C7	0.0530 (2)	0.1886 (3)	0.4137 (3)	0.0607 (11)
H7A	0.0020	0.1922	0.3735	0.091*
H7B	0.0710	0.2124	0.3695	0.091*
H7C	0.0716	0.2216	0.4812	0.091*
C8	−0.0172 (2)	−0.1223 (3)	0.3645 (4)	0.0719 (13)
H8A	−0.0539	−0.1079	0.3803	0.108*
H8B	0.0023	−0.1790	0.3951	0.108*
H8C	−0.0369	−0.1236	0.2858	0.108*
C9	0.23652 (17)	−0.0451 (2)	0.5954 (3)	0.0464 (8)
H9A	0.2378	−0.1068	0.6114	0.070*
H9B	0.2595	−0.0124	0.6634	0.070*
H9C	0.2607	−0.0350	0.5553	0.070*
C10	0.30035 (17)	0.1564 (2)	0.7643 (2)	0.0394 (8)
C11	0.37154 (17)	0.1357 (2)	0.8185 (2)	0.0427 (8)
C12	0.41094 (19)	0.1333 (2)	0.9321 (3)	0.0512 (9)
H12	0.4590	0.1193	0.9670	0.061*
C13	0.3812 (2)	0.1508 (2)	0.9945 (3)	0.0541 (10)
C14	0.3113 (2)	0.1726 (2)	0.9417 (3)	0.0520 (10)
H14	0.2903	0.1858	0.9834	0.062*
C15	0.27101 (18)	0.1755 (2)	0.8287 (3)	0.0437 (8)
C16	0.40779 (19)	0.1146 (3)	0.7567 (3)	0.0576 (10)
H16A	0.3855	0.0644	0.7102	0.086*
H16B	0.4569	0.1016	0.8080	0.086*
H16C	0.4046	0.1642	0.7119	0.086*
C17	0.4242 (2)	0.1459 (3)	1.1178 (3)	0.0770 (14)
H17A	0.4729	0.1341	1.1407	0.115*
H17B	0.4062	0.0994	1.1433	0.115*
H17C	0.4210	0.2009	1.1488	0.115*
C18	0.19456 (18)	0.1971 (3)	0.7786 (3)	0.0541 (10)
H18A	0.1883	0.2598	0.7698	0.081*
H18B	0.1779	0.1764	0.8260	0.081*
H18C	0.1680	0.1692	0.7076	0.081*
C19	0.29184 (17)	0.3701 (2)	0.6794 (2)	0.0414 (8)
H19A	0.2829	0.3512	0.7371	0.050*
H19B	0.3352	0.3416	0.6930	0.050*
C20	0.30422 (19)	0.4667 (2)	0.6901 (3)	0.0496 (9)
H20A	0.3211	0.4852	0.6421	0.074*
H20B	0.3390	0.4808	0.7653	0.074*
H20C	0.2605	0.4965	0.6698	0.074*
C21	0.14350 (17)	0.3982 (2)	0.5211 (3)	0.0441 (8)
H21A	0.1544	0.4590	0.5144	0.053*
H21B	0.1031	0.3809	0.4505	0.053*
C22	0.12205 (18)	0.3937 (3)	0.6068 (3)	0.0527 (9)
H22A	0.1039	0.3360	0.6063	0.079*
H22B	0.0859	0.4369	0.5905	0.079*
H22C	0.1626	0.4053	0.6785	0.079*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
In1	0.02880 (13)	0.04999 (15)	0.01987 (11)	−0.01078 (11)	0.00826 (9)	0.00045 (10)
P1	0.0310 (4)	0.0489 (5)	0.0237 (4)	−0.0081 (4)	0.0122 (3)	−0.0014 (4)
C1	0.0328 (17)	0.053 (2)	0.0194 (14)	−0.0126 (15)	0.0121 (13)	−0.0020 (14)
C2	0.0355 (19)	0.059 (2)	0.0300 (17)	−0.0130 (17)	0.0137 (15)	−0.0048 (16)
C3	0.0330 (19)	0.070 (3)	0.043 (2)	−0.0120 (18)	0.0159 (16)	−0.0112 (18)
C4	0.042 (2)	0.071 (3)	0.046 (2)	−0.026 (2)	0.0267 (18)	−0.0234 (19)
C5	0.057 (2)	0.050 (2)	0.045 (2)	−0.0126 (18)	0.0349 (19)	−0.0124 (16)
C6	0.0377 (18)	0.054 (2)	0.0261 (15)	−0.0101 (16)	0.0188 (14)	−0.0049 (14)
C7	0.038 (2)	0.068 (3)	0.052 (2)	−0.0092 (19)	0.0052 (18)	0.0079 (19)
C8	0.061 (3)	0.085 (3)	0.077 (3)	−0.038 (2)	0.040 (2)	−0.035 (3)
C9	0.045 (2)	0.053 (2)	0.0365 (19)	−0.0034 (18)	0.0176 (17)	0.0005 (16)
C10	0.0374 (18)	0.050 (2)	0.0220 (15)	−0.0155 (16)	0.0089 (13)	0.0015 (14)
C11	0.0372 (19)	0.057 (2)	0.0255 (16)	−0.0129 (16)	0.0098 (14)	0.0013 (14)
C12	0.038 (2)	0.068 (2)	0.0303 (18)	−0.0126 (18)	0.0045 (15)	0.0032 (16)
C13	0.056 (2)	0.069 (3)	0.0236 (17)	−0.021 (2)	0.0109 (16)	0.0005 (16)
C14	0.053 (2)	0.072 (3)	0.0273 (17)	−0.018 (2)	0.0175 (16)	−0.0053 (17)
C15	0.0394 (19)	0.058 (2)	0.0277 (16)	−0.0146 (17)	0.0128 (14)	0.0006 (15)
C16	0.040 (2)	0.091 (3)	0.0348 (19)	−0.004 (2)	0.0141 (17)	0.002 (2)
C17	0.072 (3)	0.112 (4)	0.0230 (18)	−0.021 (3)	0.0070 (18)	0.002 (2)
C18	0.044 (2)	0.080 (3)	0.039 (2)	−0.007 (2)	0.0216 (18)	0.0019 (18)
C19	0.0381 (19)	0.058 (2)	0.0238 (16)	−0.0072 (16)	0.0126 (14)	−0.0021 (14)
C20	0.055 (2)	0.060 (2)	0.0350 (19)	−0.0194 (19)	0.0234 (17)	−0.0112 (16)
C21	0.0364 (19)	0.057 (2)	0.0365 (18)	−0.0003 (17)	0.0165 (15)	0.0003 (16)
C22	0.041 (2)	0.078 (3)	0.0373 (19)	−0.004 (2)	0.0193 (17)	−0.0078 (18)

Geometric parameters (Å, º) top

In1—C1	2.190 (3)	C11—C16	1.509 (5)
In1—C10	2.215 (3)	C12—C13	1.385 (5)
In1—P1	2.6300 (12)	C12—H12	0.9500
In1—P1ⁱ	2.6364 (9)	C13—C14	1.386 (5)
P1—C21	1.856 (3)	C13—C17	1.524 (5)
P1—C19	1.866 (3)	C14—C15	1.397 (4)
P1—In1ⁱ	2.6364 (9)	C14—H14	0.9500
C1—C2	1.406 (4)	C15—C18	1.514 (5)
C1—C6	1.409 (5)	C16—H16A	0.9800
C2—C3	1.386 (5)	C16—H16B	0.9800
C2—C7	1.512 (5)	C16—H16C	0.9800
C3—C4	1.384 (5)	C17—H17A	0.9800
C3—H3	0.9500	C17—H17B	0.9800
C4—C5	1.392 (5)	C17—H17C	0.9800
C4—C8	1.511 (5)	C18—H18A	0.9800
C5—C6	1.398 (4)	C18—H18B	0.9800
C5—H5	0.9500	C18—H18C	0.9800
C6—C9	1.510 (4)	C19—C20	1.515 (5)
C7—H7A	0.9800	C19—H19A	0.9900
C7—H7B	0.9800	C19—H19B	0.9900
C7—H7C	0.9800	C20—H20A	0.9800
C8—H8A	0.9800	C20—H20B	0.9800
C8—H8B	0.9800	C20—H20C	0.9800
C8—H8C	0.9800	C21—C22	1.530 (4)
C9—H9A	0.9800	C21—H21A	0.9900
C9—H9B	0.9800	C21—H21B	0.9900
C9—H9C	0.9800	C22—H22A	0.9800
C10—C11	1.405 (5)	C22—H22B	0.9800
C10—C15	1.408 (5)	C22—H22C	0.9800
C11—C12	1.402 (4)

C1—In1—C10	117.60 (11)	C13—C12—C11	121.4 (3)
C1—In1—P1	123.68 (9)	C13—C12—H12	119.3
C10—In1—P1	103.40 (9)	C11—C12—H12	119.3
C1—In1—P1ⁱ	104.11 (7)	C12—C13—C14	118.2 (3)
C10—In1—P1ⁱ	122.61 (9)	C12—C13—C17	120.9 (4)
P1—In1—P1ⁱ	81.56 (3)	C14—C13—C17	120.9 (4)
C21—P1—C19	104.40 (16)	C13—C14—C15	121.4 (3)
C21—P1—In1	125.97 (11)	C13—C14—H14	119.3
C19—P1—In1	99.36 (11)	C15—C14—H14	119.3
C21—P1—In1ⁱ	120.44 (11)	C14—C15—C10	120.9 (3)
C19—P1—In1ⁱ	104.85 (10)	C14—C15—C18	117.5 (3)
In1—P1—In1ⁱ	98.44 (3)	C10—C15—C18	121.6 (3)
C2—C1—C6	118.1 (3)	C11—C16—H16A	109.5
C2—C1—In1	125.1 (2)	C11—C16—H16B	109.5
C6—C1—In1	116.8 (2)	H16A—C16—H16B	109.5
C3—C2—C1	120.3 (3)	C11—C16—H16C	109.5
C3—C2—C7	118.4 (3)	H16A—C16—H16C	109.5
C1—C2—C7	121.3 (3)	H16B—C16—H16C	109.5
C4—C3—C2	122.1 (3)	C13—C17—H17A	109.5
C4—C3—H3	119.0	C13—C17—H17B	109.5
C2—C3—H3	119.0	H17A—C17—H17B	109.5
C3—C4—C5	117.9 (3)	C13—C17—H17C	109.5
C3—C4—C8	120.8 (4)	H17A—C17—H17C	109.5
C5—C4—C8	121.3 (4)	H17B—C17—H17C	109.5
C4—C5—C6	121.5 (3)	C15—C18—H18A	109.5
C4—C5—H5	119.3	C15—C18—H18B	109.5
C6—C5—H5	119.3	H18A—C18—H18B	109.5
C5—C6—C1	120.1 (3)	C15—C18—H18C	109.5
C5—C6—C9	119.1 (3)	H18A—C18—H18C	109.5
C1—C6—C9	120.8 (3)	H18B—C18—H18C	109.5
C2—C7—H7A	109.5	C20—C19—P1	116.6 (2)
C2—C7—H7B	109.5	C20—C19—H19A	108.1
H7A—C7—H7B	109.5	P1—C19—H19A	108.1
C2—C7—H7C	109.5	C20—C19—H19B	108.1
H7A—C7—H7C	109.5	P1—C19—H19B	108.1
H7B—C7—H7C	109.5	H19A—C19—H19B	107.3
C4—C8—H8A	109.5	C19—C20—H20A	109.5
C4—C8—H8B	109.5	C19—C20—H20B	109.5
H8A—C8—H8B	109.5	H20A—C20—H20B	109.5
C4—C8—H8C	109.5	C19—C20—H20C	109.5
H8A—C8—H8C	109.5	H20A—C20—H20C	109.5
H8B—C8—H8C	109.5	H20B—C20—H20C	109.5
C6—C9—H9A	109.5	C22—C21—P1	116.1 (2)
C6—C9—H9B	109.5	C22—C21—H21A	108.3
H9A—C9—H9B	109.5	P1—C21—H21A	108.3
C6—C9—H9C	109.5	C22—C21—H21B	108.3
H9A—C9—H9C	109.5	P1—C21—H21B	108.3
H9B—C9—H9C	109.5	H21A—C21—H21B	107.4
C11—C10—C15	117.3 (3)	C21—C22—H22A	109.5
C11—C10—In1	124.8 (2)	C21—C22—H22B	109.5
C15—C10—In1	117.9 (2)	H22A—C22—H22B	109.5
C12—C11—C10	120.8 (3)	C21—C22—H22C	109.5
C12—C11—C16	118.0 (3)	H22A—C22—H22C	109.5
C10—C11—C16	121.2 (3)	H22B—C22—H22C	109.5

Symmetry code: (i) −x+1/2, −y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula	[In₂(C₉H₁₁)₄(C₄H₁₀P)₂]
M_r	884.53
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	198
a, b, c (Å)	22.323 (4), 15.494 (4), 14.331 (3)
β (°)	120.618 (4)
V (Å³)	4265.6 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.18
Crystal size (mm)	0.23 × 0.20 × 0.01

Data collection
Diffractometer	Bruker SMART1000/P4 diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2008a)
T_min, T_max	0.777, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	14538, 4771, 3470
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.078, 1.09
No. of reflections	4771
No. of parameters	225
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.65, −0.34

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008b), SHELXL97 (Sheldrick, 2008b), DIAMOND (Brandenburg, 2011), SHELXTL (Sheldrick, 2008b).

Acknowledgements

This work was supported by the Natural Sciences and Engineering Research Council of Canada, the New Brunswick Innovation Foundation, the Canadian Foundation for Innovation and Mount Allison University.

References

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