cis-[1,2-Bis(diphenyl­arsan­yl)ethane-κ2As,As']tetra­carbonyl­chromium(0)

Norlidah, M.N.; Azhar, M.Y.; Bin Shawkataly, O.; Rosli, M.M.; Fun, H.-K.

doi:10.1107/S1600536811032314

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Pages m1267-m1268

doi:10.1107/S1600536811032314

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cis-[1,2-Bis(diphenylarsanyl)ethane-κ²As,As']tetracarbonylchromium(0)

M. N. Norlidah,^a ‡ M. Y. Azhar,^a Omar Bin Shawkataly,^b § Mohd Mustaqim Rosli ^c and Hoong-Kun Fun ^c ^*¶

^aFaculty of Industrial Science and Technology, Universiti Malaysia Pahang, Gambang 26300, Pahang, Malaysia, ^bChemical Sciences Programme, School of Distance Education, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 8 August 2011; accepted 9 August 2011; online 27 August 2011)

In the title compound, [Cr(C₂₆H₂₄As₂)(CO)₄], the Cr atom is octahedrally coordinated by four carbonyl ligands and one bidentate 1,2-bis(diphenylarsanyl)ethane ligand, which chelates in a cis manner with an As—Cr—As bite angle of 82.513 (9)°. The dihedral angles between the pairs of benzene rings attached to each As atom are 84.63 (9) and 77.15 (8)°. In the crystal, molecules are linked by C—H⋯O interactions, forming infinite chains along the a axis. The crystal structure is further stabilized by C—H⋯π interactions.

Related literature

X-ray structure determinations of chromium carbonyls with arsine ligands are rare. A search of the Cambridge Crystallographic Structural Database (Allen, 2002 ) reveals only 12 complexes of chromium carbonyl disubtituted with tertiary arsines. For related structures, see: Bennett et al. (1971 ); Nowell et al. (1972 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

[Cr(C₂₆H₂₄As₂)(CO)₄]
M_r = 650.33
Orthorhombic, P b c a
a = 17.0231 (4) Å
b = 12.6200 (3) Å
c = 25.5527 (6) Å
V = 5489.5 (2) Å³
Z = 8
Mo Kα radiation
μ = 2.84 mm⁻¹
T = 100 K
0.53 × 0.25 × 0.05 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.313, T_max = 0.871
87112 measured reflections
9352 independent reflections
7454 reflections with I > 2σ(I)
R_int = 0.054

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.065
S = 1.02
9352 reflections
334 parameters
H-atom parameters constrained
Δρ_max = 0.78 e Å⁻³
Δρ_min = −0.50 e Å⁻³

Table 1
Selected bond lengths (Å)

As1—Cr1	2.4461 (3)
As2—Cr1	2.4512 (3)
Cr1—C2	1.8457 (17)
Cr1—C1	1.8511 (17)
Cr1—C3	1.8894 (17)
Cr1—C4	1.8935 (18)

Table 2
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C7–C12 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9A⋯O1ⁱ	0.93	2.57	3.345 (2)	141
C16—H16A⋯Cg1ⁱⁱ	0.93	2.60	3.519 (2)	169
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ ; (ii) -x, -y, -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 I, global. DOI: 10.1107/S1600536811032314/ng5210sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811032314/ng5210Isup2.hkl

checkCIF report

Comment top

Very few chromium carbonyls with bidentate arsine ligands have been reported (Allen, 2002). The C—C bond length and the As—Cr—As bite angle of the title complex are comparable to similar complexes of chromium carbonyls substituted with bidentate arsine with two carbon atom backbone (Nowell et al.,1972). The title compound is isostructural to Cr(CO)₄(Ph₂P(CH₂)₂PPh₂) and this gives further support that the formation of stable cis-M(CO)₄L₂ compounds is prefered when the L₂ groups are combined in a chelating bidentate ligand (Bennett et al. 1971).

The Cr—As bond lengths show an average value of 2.449 Å and the As—Cr—As bite angle has a value of 82.51 (1)° (Table 1) while in Cr(CO)₄(Ph₂P(CH₂)₂PPh₂), the average of Cr—P bond lengths is 2.360Å and the P—Cr—P bite angle has a value of 83.41 (8).

In the molecule, the dihedral angle between the two benzene ring attached to the As1 and As2 are 84.63 (9)° (C7—C12 & C13—C18 rings) and 77.15 (8)° (C19—C24 & C25—C30 rings), respectively. The molecules form infinite chains along the a axis (Fig. 2) throught C9—H9A···O1ⁱ (Table 2) intermolecular interactions. The crystal structure is further stabilized by C—H···π interaction involving Cg1, Cg1 is the centroid of C7—C12 (Table 2).

Related literature top

X-ray structure determinations of chromium carbonyls with arsine ligands are rare. A search of the Cambridge Crystallographic Structural Database (Allen, 2002) reveals only 12 complexes of chromium carbonyl disubtituted with tertiary arsines. For related structures, see: Bennett et al. (1971); Nowell et al. (1972). 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 under dry oxygen free nitrogen. Chromium hexacarbonyl (200 mg, 0.909 mmol) and ethylenebisdiphenyl-arsanylethane (441.9 mg, 0.9086 mmol) in 35 ml of pet ether (100–130°C) was refluxed for 12 h. Suitable single crystals were obtained by solvent-solvent diffusion in a mixture of dichloromethane/methanol.

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, showing 50% probability displacement ellipsoids. Hydrogen atoms are shown as spheres of arbitrary radius.
	Fig. 2. The packing of (I) shown an infinite chains along a axis. Dashed lines indicate hydrogen bonds. H atoms not involved in the hydrogen bond interactions have been omitted for clarity.

cis-[1,2-Bis(diphenylarsanyl)ethane- κ²As,As']tetracarbonylchromium(0) top

Crystal data top

[Cr(C₂₆H₂₄As₂)(CO)₄]	F(000) = 2608
M_r = 650.33	D_x = 1.574 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 9793 reflections
a = 17.0231 (4) Å	θ = 2.4–31.6°
b = 12.6200 (3) Å	µ = 2.84 mm⁻¹
c = 25.5527 (6) Å	T = 100 K
V = 5489.5 (2) Å³	Plate, yellow
Z = 8	0.53 × 0.25 × 0.05 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	9352 independent reflections
Radiation source: fine-focus sealed tube	7454 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.054
ϕ and ω scans	θ_max = 31.9°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −25→25
T_min = 0.313, T_max = 0.871	k = −18→18
87112 measured reflections	l = −37→36

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.065	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0273P)² + 3.1824P] where P = (F_o² + 2F_c²)/3
9352 reflections	(Δ/σ)_max = 0.001
334 parameters	Δρ_max = 0.78 e Å⁻³
0 restraints	Δρ_min = −0.50 e Å⁻³

Crystal data top

[Cr(C₂₆H₂₄As₂)(CO)₄]	V = 5489.5 (2) Å³
M_r = 650.33	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 17.0231 (4) Å	µ = 2.84 mm⁻¹
b = 12.6200 (3) Å	T = 100 K
c = 25.5527 (6) Å	0.53 × 0.25 × 0.05 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	9352 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	7454 reflections with I > 2σ(I)
T_min = 0.313, T_max = 0.871	R_int = 0.054
87112 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	0 restraints
wR(F²) = 0.065	H-atom parameters constrained
S = 1.02	Δρ_max = 0.78 e Å⁻³
9352 reflections	Δρ_min = −0.50 e Å⁻³
334 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
As1	0.057670 (9)	0.238802 (12)	0.109865 (6)	0.01225 (4)
As2	0.018356 (9)	0.355446 (12)	0.219264 (6)	0.01278 (4)
Cr1	−0.014160 (15)	0.402272 (19)	0.128720 (10)	0.01236 (5)
O1	−0.06677 (8)	0.43384 (10)	0.01759 (5)	0.0246 (3)
O2	−0.09528 (8)	0.60856 (9)	0.15170 (5)	0.0232 (3)
O3	−0.16549 (7)	0.27784 (10)	0.14160 (5)	0.0224 (3)
O4	0.14071 (8)	0.51681 (11)	0.11081 (6)	0.0272 (3)
C1	−0.04384 (10)	0.42144 (12)	0.05967 (7)	0.0165 (3)
C2	−0.06388 (10)	0.52821 (13)	0.14459 (7)	0.0169 (3)
C3	−0.10761 (10)	0.32364 (13)	0.13788 (6)	0.0161 (3)
C4	0.08227 (10)	0.47383 (13)	0.11800 (7)	0.0175 (3)
C5	0.11061 (9)	0.19004 (12)	0.17374 (6)	0.0153 (3)
H5A	0.1228	0.1152	0.1708	0.018*
H5B	0.1595	0.2284	0.1783	0.018*
C6	0.05746 (10)	0.20852 (12)	0.22068 (6)	0.0163 (3)
H6A	0.0865	0.1962	0.2528	0.020*
H6B	0.0136	0.1595	0.2196	0.020*
C7	0.14297 (9)	0.24008 (12)	0.05972 (7)	0.0149 (3)
C8	0.20274 (10)	0.16476 (14)	0.06237 (7)	0.0206 (3)
H8A	0.2028	0.1146	0.0890	0.025*
C9	0.26242 (11)	0.16466 (16)	0.02509 (8)	0.0259 (4)
H9A	0.3026	0.1149	0.0270	0.031*
C10	0.26182 (11)	0.23863 (16)	−0.01474 (8)	0.0275 (4)
H10A	0.3015	0.2381	−0.0397	0.033*
C11	0.20263 (13)	0.31346 (16)	−0.01777 (8)	0.0293 (4)
H11A	0.2025	0.3629	−0.0448	0.035*
C12	0.14324 (11)	0.31449 (14)	0.01975 (7)	0.0231 (4)
H12A	0.1037	0.3652	0.0180	0.028*
C13	−0.00267 (9)	0.11792 (13)	0.08554 (7)	0.0152 (3)
C14	0.00004 (11)	0.01848 (14)	0.10873 (7)	0.0221 (4)
H14A	0.0320	0.0068	0.1377	0.027*
C15	−0.04515 (12)	−0.06359 (14)	0.08852 (8)	0.0259 (4)
H15A	−0.0436	−0.1300	0.1042	0.031*
C16	−0.09245 (11)	−0.04732 (14)	0.04528 (8)	0.0238 (4)
H16A	−0.1223	−0.1027	0.0319	0.029*
C17	−0.09518 (11)	0.05155 (14)	0.02200 (8)	0.0234 (4)
H17A	−0.1270	0.0627	−0.0071	0.028*
C18	−0.05043 (11)	0.13430 (13)	0.04200 (7)	0.0212 (3)
H18A	−0.0524	0.2007	0.0263	0.025*
C19	−0.06385 (9)	0.35132 (12)	0.27216 (6)	0.0142 (3)
C20	−0.05732 (10)	0.28751 (13)	0.31664 (7)	0.0184 (3)
H20A	−0.0130	0.2454	0.3212	0.022*
C21	−0.11640 (11)	0.28637 (14)	0.35403 (7)	0.0224 (4)
H21A	−0.1116	0.2436	0.3835	0.027*
C22	−0.18290 (11)	0.34913 (14)	0.34745 (7)	0.0222 (4)
H22A	−0.2224	0.3487	0.3726	0.027*
C23	−0.19024 (10)	0.41239 (14)	0.30323 (7)	0.0204 (3)
H23A	−0.2347	0.4543	0.2988	0.024*
C24	−0.13112 (10)	0.41316 (13)	0.26559 (7)	0.0172 (3)
H24A	−0.1365	0.4551	0.2359	0.021*
C25	0.10030 (9)	0.43394 (13)	0.25556 (7)	0.0160 (3)
C26	0.14419 (11)	0.39131 (14)	0.29641 (7)	0.0215 (3)
H26A	0.1367	0.3212	0.3064	0.026*
C27	0.19926 (11)	0.45346 (15)	0.32230 (8)	0.0260 (4)
H27A	0.2281	0.4248	0.3498	0.031*
C28	0.21143 (11)	0.55748 (15)	0.30750 (8)	0.0269 (4)
H28A	0.2484	0.5986	0.3250	0.032*
C29	0.16864 (11)	0.60052 (14)	0.26664 (8)	0.0237 (4)
H29A	0.1771	0.6703	0.2564	0.028*
C30	0.11286 (10)	0.53888 (13)	0.24094 (7)	0.0183 (3)
H30B	0.0837	0.5681	0.2137	0.022*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
As1	0.01221 (7)	0.01282 (7)	0.01172 (8)	0.00059 (5)	0.00040 (6)	−0.00029 (5)
As2	0.01295 (8)	0.01347 (7)	0.01191 (8)	0.00115 (5)	−0.00018 (6)	−0.00042 (5)
Cr1	0.01258 (12)	0.01213 (11)	0.01236 (12)	0.00032 (8)	−0.00026 (9)	0.00065 (9)
O1	0.0237 (7)	0.0300 (7)	0.0200 (7)	−0.0057 (5)	−0.0055 (5)	0.0078 (5)
O2	0.0222 (6)	0.0174 (6)	0.0300 (7)	0.0035 (5)	0.0000 (6)	−0.0021 (5)
O3	0.0193 (6)	0.0236 (6)	0.0244 (7)	−0.0038 (5)	−0.0008 (5)	0.0022 (5)
O4	0.0232 (7)	0.0283 (7)	0.0300 (7)	−0.0092 (5)	0.0042 (6)	−0.0022 (6)
C1	0.0151 (7)	0.0155 (7)	0.0187 (8)	−0.0023 (5)	0.0004 (6)	0.0015 (6)
C2	0.0164 (8)	0.0186 (7)	0.0158 (8)	−0.0018 (6)	−0.0014 (6)	0.0006 (6)
C3	0.0191 (8)	0.0159 (7)	0.0133 (8)	0.0028 (6)	−0.0016 (6)	0.0013 (6)
C4	0.0210 (8)	0.0164 (7)	0.0149 (8)	0.0013 (6)	0.0006 (6)	−0.0016 (6)
C5	0.0159 (7)	0.0152 (7)	0.0148 (8)	0.0021 (5)	−0.0004 (6)	0.0002 (6)
C6	0.0193 (8)	0.0147 (7)	0.0149 (8)	0.0023 (6)	0.0010 (6)	0.0001 (6)
C7	0.0126 (7)	0.0171 (7)	0.0151 (8)	−0.0022 (5)	0.0017 (6)	−0.0032 (6)
C8	0.0175 (8)	0.0293 (9)	0.0149 (8)	0.0042 (7)	−0.0003 (7)	−0.0004 (7)
C9	0.0156 (8)	0.0412 (11)	0.0208 (9)	0.0045 (7)	0.0015 (7)	−0.0057 (8)
C10	0.0205 (9)	0.0397 (11)	0.0223 (9)	−0.0073 (8)	0.0086 (7)	−0.0067 (8)
C11	0.0371 (11)	0.0269 (9)	0.0240 (10)	−0.0047 (8)	0.0111 (9)	0.0038 (8)
C12	0.0269 (9)	0.0197 (8)	0.0228 (9)	0.0008 (7)	0.0062 (8)	0.0014 (7)
C13	0.0137 (7)	0.0163 (7)	0.0154 (8)	−0.0002 (5)	0.0024 (6)	−0.0032 (6)
C14	0.0278 (9)	0.0219 (8)	0.0166 (8)	−0.0061 (7)	−0.0036 (7)	0.0014 (6)
C15	0.0353 (11)	0.0192 (8)	0.0232 (9)	−0.0078 (7)	−0.0026 (8)	0.0016 (7)
C16	0.0219 (9)	0.0245 (8)	0.0251 (10)	−0.0058 (7)	0.0018 (8)	−0.0078 (7)
C17	0.0217 (9)	0.0248 (8)	0.0237 (9)	0.0022 (7)	−0.0091 (7)	−0.0052 (7)
C18	0.0233 (9)	0.0184 (7)	0.0218 (9)	0.0026 (6)	−0.0057 (7)	−0.0020 (6)
C19	0.0149 (7)	0.0143 (7)	0.0134 (7)	−0.0015 (5)	0.0011 (6)	−0.0019 (5)
C20	0.0199 (8)	0.0155 (7)	0.0197 (8)	0.0018 (6)	0.0002 (7)	−0.0006 (6)
C21	0.0287 (9)	0.0195 (8)	0.0189 (9)	−0.0015 (7)	0.0039 (7)	0.0030 (6)
C22	0.0209 (8)	0.0240 (8)	0.0217 (9)	−0.0039 (7)	0.0078 (7)	−0.0025 (7)
C23	0.0160 (8)	0.0212 (8)	0.0240 (9)	−0.0001 (6)	0.0016 (7)	−0.0011 (7)
C24	0.0166 (8)	0.0179 (7)	0.0171 (8)	0.0009 (6)	−0.0005 (6)	0.0000 (6)
C25	0.0133 (7)	0.0194 (7)	0.0152 (8)	0.0012 (6)	0.0004 (6)	−0.0028 (6)
C26	0.0216 (9)	0.0234 (8)	0.0197 (9)	0.0025 (7)	−0.0030 (7)	0.0001 (7)
C27	0.0202 (9)	0.0329 (10)	0.0247 (10)	0.0072 (7)	−0.0096 (8)	−0.0061 (8)
C28	0.0172 (8)	0.0310 (9)	0.0326 (11)	0.0021 (7)	−0.0057 (8)	−0.0136 (8)
C29	0.0200 (8)	0.0198 (8)	0.0314 (10)	0.0018 (6)	−0.0023 (7)	−0.0075 (7)
C30	0.0166 (8)	0.0184 (7)	0.0198 (9)	0.0026 (6)	−0.0017 (6)	−0.0035 (6)

Geometric parameters (Å, º) top

As1—C7	1.9367 (16)	C13—C18	1.393 (2)
As1—C13	1.9413 (16)	C14—C15	1.390 (2)
As1—C5	1.9634 (16)	C14—H14A	0.9300
As1—Cr1	2.4461 (3)	C15—C16	1.382 (3)
As2—C25	1.9461 (16)	C15—H15A	0.9300
As2—C19	1.9463 (16)	C16—C17	1.383 (3)
As2—C6	1.9704 (16)	C16—H16A	0.9300
As2—Cr1	2.4512 (3)	C17—C18	1.390 (2)
Cr1—C2	1.8457 (17)	C17—H17A	0.9300
Cr1—C1	1.8511 (17)	C18—H18A	0.9300
Cr1—C3	1.8894 (17)	C19—C24	1.396 (2)
Cr1—C4	1.8935 (18)	C19—C20	1.397 (2)
O1—C1	1.155 (2)	C20—C21	1.387 (2)
O2—C2	1.161 (2)	C20—H20A	0.9300
O3—C3	1.146 (2)	C21—C22	1.392 (3)
O4—C4	1.148 (2)	C21—H21A	0.9300
C5—C6	1.520 (2)	C22—C23	1.389 (3)
C5—H5A	0.9700	C22—H22A	0.9300
C5—H5B	0.9700	C23—C24	1.392 (2)
C6—H6A	0.9700	C23—H23A	0.9300
C6—H6B	0.9700	C24—H24A	0.9300
C7—C12	1.387 (2)	C25—C26	1.392 (2)
C7—C8	1.394 (2)	C25—C30	1.392 (2)
C8—C9	1.393 (3)	C26—C27	1.390 (3)
C8—H8A	0.9300	C26—H26A	0.9300
C9—C10	1.381 (3)	C27—C28	1.382 (3)
C9—H9A	0.9300	C27—H27A	0.9300
C10—C11	1.383 (3)	C28—C29	1.384 (3)
C10—H10A	0.9300	C28—H28A	0.9300
C11—C12	1.393 (3)	C29—C30	1.392 (2)
C11—H11A	0.9300	C29—H29A	0.9300
C12—H12A	0.9300	C30—H30B	0.9300
C13—C14	1.389 (2)

C7—As1—C13	101.03 (7)	C7—C12—C11	120.17 (17)
C7—As1—C5	102.03 (7)	C7—C12—H12A	119.9
C13—As1—C5	105.23 (7)	C11—C12—H12A	119.9
C7—As1—Cr1	119.87 (5)	C14—C13—C18	119.62 (16)
C13—As1—Cr1	117.47 (5)	C14—C13—As1	123.77 (13)
C5—As1—Cr1	109.27 (5)	C18—C13—As1	116.60 (12)
C25—As2—C19	101.42 (7)	C13—C14—C15	119.77 (17)
C25—As2—C6	103.18 (7)	C13—C14—H14A	120.1
C19—As2—C6	101.83 (7)	C15—C14—H14A	120.1
C25—As2—Cr1	119.27 (5)	C16—C15—C14	120.58 (17)
C19—As2—Cr1	119.97 (5)	C16—C15—H15A	119.7
C6—As2—Cr1	108.69 (5)	C14—C15—H15A	119.7
C2—Cr1—C1	88.38 (7)	C15—C16—C17	119.82 (17)
C2—Cr1—C3	92.23 (7)	C15—C16—H16A	120.1
C1—Cr1—C3	87.53 (7)	C17—C16—H16A	120.1
C2—Cr1—C4	91.07 (7)	C16—C17—C18	120.08 (17)
C1—Cr1—C4	92.09 (7)	C16—C17—H17A	120.0
C3—Cr1—C4	176.66 (7)	C18—C17—H17A	120.0
C2—Cr1—As1	177.11 (5)	C17—C18—C13	120.13 (16)
C1—Cr1—As1	93.38 (5)	C17—C18—H18A	119.9
C3—Cr1—As1	90.13 (5)	C13—C18—H18A	119.9
C4—Cr1—As1	86.58 (5)	C24—C19—C20	119.03 (15)
C2—Cr1—As2	95.95 (5)	C24—C19—As2	119.43 (12)
C1—Cr1—As2	173.10 (5)	C20—C19—As2	121.54 (12)
C3—Cr1—As2	86.94 (5)	C21—C20—C19	120.56 (16)
C4—Cr1—As2	93.20 (5)	C21—C20—H20A	119.7
As1—Cr1—As2	82.513 (9)	C19—C20—H20A	119.7
O1—C1—Cr1	176.05 (15)	C20—C21—C22	120.04 (17)
O2—C2—Cr1	176.30 (15)	C20—C21—H21A	120.0
O3—C3—Cr1	177.18 (15)	C22—C21—H21A	120.0
O4—C4—Cr1	179.09 (16)	C23—C22—C21	119.90 (16)
C6—C5—As1	109.55 (11)	C23—C22—H22A	120.0
C6—C5—H5A	109.8	C21—C22—H22A	120.0
As1—C5—H5A	109.8	C22—C23—C24	120.07 (16)
C6—C5—H5B	109.8	C22—C23—H23A	120.0
As1—C5—H5B	109.8	C24—C23—H23A	120.0
H5A—C5—H5B	108.2	C23—C24—C19	120.39 (16)
C5—C6—As2	109.32 (11)	C23—C24—H24A	119.8
C5—C6—H6A	109.8	C19—C24—H24A	119.8
As2—C6—H6A	109.8	C26—C25—C30	119.10 (16)
C5—C6—H6B	109.8	C26—C25—As2	123.05 (13)
As2—C6—H6B	109.8	C30—C25—As2	117.80 (12)
H6A—C6—H6B	108.3	C27—C26—C25	120.06 (17)
C12—C7—C8	119.66 (16)	C27—C26—H26A	120.0
C12—C7—As1	119.68 (13)	C25—C26—H26A	120.0
C8—C7—As1	120.62 (13)	C28—C27—C26	120.47 (18)
C9—C8—C7	119.99 (17)	C28—C27—H27A	119.8
C9—C8—H8A	120.0	C26—C27—H27A	119.8
C7—C8—H8A	120.0	C27—C28—C29	120.02 (17)
C10—C9—C8	119.87 (18)	C27—C28—H28A	120.0
C10—C9—H9A	120.1	C29—C28—H28A	120.0
C8—C9—H9A	120.1	C28—C29—C30	119.70 (17)
C9—C10—C11	120.54 (18)	C28—C29—H29A	120.1
C9—C10—H10A	119.7	C30—C29—H29A	120.1
C11—C10—H10A	119.7	C29—C30—C25	120.64 (17)
C10—C11—C12	119.76 (18)	C29—C30—H30B	119.7
C10—C11—H11A	120.1	C25—C30—H30B	119.7
C12—C11—H11A	120.1

C7—As1—Cr1—C1	58.18 (8)	C10—C11—C12—C7	−0.7 (3)
C13—As1—Cr1—C1	−65.02 (8)	C7—As1—C13—C14	101.21 (16)
C5—As1—Cr1—C1	175.28 (7)	C5—As1—C13—C14	−4.64 (17)
C7—As1—Cr1—C3	145.71 (8)	Cr1—As1—C13—C14	−126.46 (14)
C13—As1—Cr1—C3	22.52 (8)	C7—As1—C13—C18	−78.32 (14)
C5—As1—Cr1—C3	−97.19 (7)	C5—As1—C13—C18	175.83 (13)
C7—As1—Cr1—C4	−33.72 (8)	Cr1—As1—C13—C18	54.01 (14)
C13—As1—Cr1—C4	−156.91 (8)	C18—C13—C14—C15	−0.3 (3)
C5—As1—Cr1—C4	83.38 (7)	As1—C13—C14—C15	−179.84 (14)
C7—As1—Cr1—As2	−127.40 (6)	C13—C14—C15—C16	0.4 (3)
C13—As1—Cr1—As2	109.41 (6)	C14—C15—C16—C17	−0.3 (3)
C5—As1—Cr1—As2	−10.30 (5)	C15—C16—C17—C18	0.1 (3)
C25—As2—Cr1—C2	−72.21 (7)	C16—C17—C18—C13	0.0 (3)
C19—As2—Cr1—C2	53.61 (7)	C14—C13—C18—C17	0.1 (3)
C6—As2—Cr1—C2	170.04 (7)	As1—C13—C18—C17	179.67 (14)
C25—As2—Cr1—C3	−164.14 (7)	C25—As2—C19—C24	107.98 (13)
C19—As2—Cr1—C3	−38.31 (7)	C6—As2—C19—C24	−145.76 (13)
C6—As2—Cr1—C3	78.11 (7)	Cr1—As2—C19—C24	−25.84 (14)
C25—As2—Cr1—C4	19.20 (7)	C25—As2—C19—C20	−72.24 (14)
C19—As2—Cr1—C4	145.03 (7)	C6—As2—C19—C20	34.03 (15)
C6—As2—Cr1—C4	−98.55 (7)	Cr1—As2—C19—C20	153.95 (11)
C25—As2—Cr1—As1	105.32 (5)	C24—C19—C20—C21	−0.7 (2)
C19—As2—Cr1—As1	−128.85 (5)	As2—C19—C20—C21	179.55 (13)
C7—As1—C5—C6	166.75 (11)	C19—C20—C21—C22	0.0 (3)
C13—As1—C5—C6	−88.13 (12)	C20—C21—C22—C23	0.4 (3)
Cr1—As1—C5—C6	38.86 (11)	C21—C22—C23—C24	−0.1 (3)
As1—C5—C6—As2	−49.63 (13)	C22—C23—C24—C19	−0.6 (3)
C25—As2—C6—C5	−87.01 (12)	C20—C19—C24—C23	1.0 (2)
C19—As2—C6—C5	168.11 (11)	As2—C19—C24—C23	−179.24 (13)
Cr1—As2—C6—C5	40.54 (12)	C19—As2—C25—C26	72.05 (15)
C13—As1—C7—C12	103.78 (14)	C6—As2—C25—C26	−33.15 (16)
C5—As1—C7—C12	−147.84 (14)	Cr1—As2—C25—C26	−153.72 (13)
Cr1—As1—C7—C12	−27.06 (16)	C19—As2—C25—C30	−105.36 (14)
C13—As1—C7—C8	−74.09 (14)	C6—As2—C25—C30	149.44 (13)
C5—As1—C7—C8	34.29 (15)	Cr1—As2—C25—C30	28.87 (15)
Cr1—As1—C7—C8	155.07 (12)	C30—C25—C26—C27	0.5 (3)
C12—C7—C8—C9	0.2 (3)	As2—C25—C26—C27	−176.90 (14)
As1—C7—C8—C9	178.04 (14)	C25—C26—C27—C28	−0.6 (3)
C7—C8—C9—C10	−0.6 (3)	C26—C27—C28—C29	0.0 (3)
C8—C9—C10—C11	0.4 (3)	C27—C28—C29—C30	0.6 (3)
C9—C10—C11—C12	0.2 (3)	C28—C29—C30—C25	−0.7 (3)
C8—C7—C12—C11	0.5 (3)	C26—C25—C30—C29	0.2 (3)
As1—C7—C12—C11	−177.42 (15)	As2—C25—C30—C29	177.68 (13)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C7–C12 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O1ⁱ	0.93	2.57	3.345 (2)	141
C16—H16A···Cg1ⁱⁱ	0.93	2.60	3.519 (2)	169

Symmetry codes: (i) x+1/2, −y+1/2, −z; (ii) −x, −y, −z.

Experimental details

Crystal data
Chemical formula	[Cr(C₂₆H₂₄As₂)(CO)₄]
M_r	650.33
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	100
a, b, c (Å)	17.0231 (4), 12.6200 (3), 25.5527 (6)
V (Å³)	5489.5 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	2.84
Crystal size (mm)	0.53 × 0.25 × 0.05

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.313, 0.871
No. of measured, independent and observed [I > 2σ(I)] reflections	87112, 9352, 7454
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.743

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.065, 1.02
No. of reflections	9352
No. of parameters	334
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.78, −0.50

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

Selected bond lengths (Å) top

As1—Cr1	2.4461 (3)	Cr1—C1	1.8511 (17)
As2—Cr1	2.4512 (3)	Cr1—C3	1.8894 (17)
Cr1—C2	1.8457 (17)	Cr1—C4	1.8935 (18)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C7–C12 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O1ⁱ	0.93	2.57	3.345 (2)	141
C16—H16A···Cg1ⁱⁱ	0.93	2.60	3.519 (2)	169

Symmetry codes: (i) x+1/2, −y+1/2, −z; (ii) −x, −y, −z.

Footnotes

‡Thomson Reuters Researcher ID: D-6198-2011.

§Additional correspondence author, e-mail: omarsa@usm.my. Thomson Reuters ResearcherID: B-6034-2009.

¶Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors would like to thank the Malaysian Government and Universiti Sains Malaysia for the Research Grant 1001/PJJauh/811115. HKF thanks USM for the Research University Grant No. 1001/PFIZIK/811160. MNN is grateful to Universiti Malaysia Pahang for a research position.

References

Allen, F. H. (2002). Acta Cryst. B58, 380–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Bennett, M. J., Cotton, F. A. & LaPrade, M. D. (1971). Acta Cryst. B27, 1899–1904. CSD CrossRef IUCr Journals Web of Science Google Scholar
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
Nowell, I. W., Rettig, S. & Trotter, J. (1972). J. Chem. Soc. Dalton Trans. pp. 2381–2388. 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

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Volume 67| Part 9| September 2011| Pages m1267-m1268

doi:10.1107/S1600536811032314

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