trans-Tetra­carbonyl­bis­[tris­(4-fluoro­phen­yl)phosphane-κP]chromium(0)

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

doi:10.1107/S1600536811033939

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Pages m1314-m1315

doi:10.1107/S1600536811033939

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trans-Tetracarbonylbis[tris(4-fluorophenyl)phosphane-κP]chromium(0)

M. N. Norlidah,^a ‡ F. M. Y. Hamdya,^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 15 August 2011; accepted 19 August 2011; online 27 August 2011)

In the title compound, [Cr(C₁₈H₁₂F₃P)₂(CO)₄], the Cr atom is octahedrally coordinated by four carbonyl ligands and the two tertiary phosphanes that are trans to each other. The Cr atom and two carbonyl groups are on a twofold axis. The benzene rings attached to the phosphorus atom make dihedral angles of 80.32 (5), 52.91 (5) and 83.80 (5)° with each other. In the crystal, C—H⋯O and C—H⋯F intermolecular interactions form an infinite three-dimensional network.

Related literature

For the crystal structures of phosphane complexes of carbonylchromium compounds, see: Preston et al. (1972 ); bin Shawkataly et al. (1996 , 2009 ). For related structures, see: Brunet et al. (2002 ); Bennett et al. (2004 ). A search of the Cambridge Structural Database (Allen, 2002 ) reveals 113 complexes of carbonylchromium complexes with bis-phosphanes. For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

[Cr(C₁₈H₁₂F₃P)₂(CO)₄]
M_r = 796.53
Monoclinic, C 2/c
a = 11.9318 (8) Å
b = 18.0956 (8) Å
c = 15.8195 (8) Å
β = 92.740 (1)°
V = 3411.7 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.51 mm⁻¹
T = 100 K
0.29 × 0.21 × 0.19 mm

Data collection

Bruker APEX Duo CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.869, T_max = 0.912
35263 measured reflections
5028 independent reflections
4627 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.026
wR(F²) = 0.074
S = 1.04
5028 reflections
242 parameters
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Selected bond lengths (Å)

Cr1—C37	1.8808 (17)
Cr1—C38	1.8925 (11)
Cr1—C39	1.8989 (15)
Cr1—P1	2.3331 (3)
Symmetry code: (i) $[-x, y, -z+{\script{1\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4A⋯O1ⁱⁱ	0.93	2.55	3.4602 (16)	165
C8—H8A⋯F1ⁱⁱⁱ	0.93	2.48	3.3830 (16)	165
C14—H14A⋯F3^iv	0.93	2.46	3.3561 (14)	161
Symmetry codes: (ii) $[x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (iii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iv) $[-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ .

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/S1600536811033939/ng5213sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811033939/ng5213Isup2.hkl

checkCIF report

Comment top

The bonding characteristics of metal carbonyls with a phosphane ligand in phosphane-substituted metal carbonyls are interesting. Several crystal structures of phosphane substituted group 6 carbonyls with trans coordination of phosphane are reported (Brunet et al. 2002; Bennett et al., 2004).

In the title compound, the Cr—P bond lengths, with an average value of 2.3331 (3) Å (Table 1) are relatively short in spite of the presence of the bulky phosphane ligand compared to the average values of 2.3656 (16)Å in the complex trans-Cr(CO)₄(PPh₃)₂ (Bennett et al. 2004).

The Cr1, O1, O3, C37 C39 atoms lie on a twofold axis. The three benzene rings attached to the phosphorus atom make dihedral angles of 80.32 (5)° (between C1—C6 & C7—C12), 52.91 (5)° (between C1—C6 & C13—C18) and 83.80 (5)° (between C7—C12 & C13—C18) with each other.

In the crystal, the molecules are interconnected by intermolecular C4—H4A···O1ⁱⁱ, C8—H8A···F1ⁱⁱⁱ and C14—H14A···F3^iv interactions (Table 2) to form an infinite three-dimensional network (Fig. 2).

Related literature top

For the crystal structures of phosphane complexes of carbonlychromiums, see: Preston et al. (1972); bin Shawkataly et al. (1996, 2009). For related structures, see: Brunet et al. (2002); Bennett et al. (2004). A search of the Cambridge Structural Database reveals 113 complexes of carbonylchromium complexes with bis-phosphanes; see: Allen (2002). 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 tris(4-flurophenyl)phosphane (301.8 mg, 0.9542 mmol) in 30 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 crystal packing of (I). Dashed lines indicate hydrogen bonds. H atoms not involved in the hydrogen bond interactions have been omitted for clarity.

trans-Tetracarbonylbis[tris(4-fluorophenyl)phosphane- κP]chromium(0) top

Crystal data top

[Cr(C₁₈H₁₂F₃P)₂(CO)₄]	F(000) = 1616
M_r = 796.53	D_x = 1.551 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 9233 reflections
a = 11.9318 (8) Å	θ = 2.4–30.1°
b = 18.0956 (8) Å	µ = 0.51 mm⁻¹
c = 15.8195 (8) Å	T = 100 K
β = 92.740 (1)°	Block, colourless
V = 3411.7 (3) Å³	0.29 × 0.21 × 0.19 mm
Z = 4

Data collection top

Bruker APEX Duo CCD area-detector diffractometer	5028 independent reflections
Radiation source: fine-focus sealed tube	4627 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ϕ and ω scans	θ_max = 30.1°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −16→16
T_min = 0.869, T_max = 0.912	k = −25→25
35263 measured reflections	l = −22→22

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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.074	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.035P)² + 3.7272P] where P = (F_o² + 2F_c²)/3
5028 reflections	(Δ/σ)_max = 0.001
242 parameters	Δρ_max = 0.42 e Å⁻³
0 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

[Cr(C₁₈H₁₂F₃P)₂(CO)₄]	V = 3411.7 (3) Å³
M_r = 796.53	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 11.9318 (8) Å	µ = 0.51 mm⁻¹
b = 18.0956 (8) Å	T = 100 K
c = 15.8195 (8) Å	0.29 × 0.21 × 0.19 mm
β = 92.740 (1)°

Data collection top

Bruker APEX Duo CCD area-detector diffractometer	5028 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4627 reflections with I > 2σ(I)
T_min = 0.869, T_max = 0.912	R_int = 0.022
35263 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	0 restraints
wR(F²) = 0.074	H-atom parameters constrained
S = 1.04	Δρ_max = 0.42 e Å⁻³
5028 reflections	Δρ_min = −0.47 e Å⁻³
242 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
Cr1	0.0000	0.470721 (12)	0.2500	0.01127 (6)
P1	0.18184 (2)	0.464307 (14)	0.310682 (16)	0.01170 (6)
F1	0.47047 (7)	0.30568 (5)	0.07445 (5)	0.03078 (18)
F2	0.27164 (8)	0.30623 (5)	0.63765 (5)	0.0368 (2)
F3	0.37981 (7)	0.75534 (4)	0.41277 (5)	0.02655 (16)
O1	0.0000	0.63797 (7)	0.2500	0.0450 (4)
O2	0.08864 (8)	0.48305 (6)	0.07365 (6)	0.0300 (2)
O3	0.0000	0.30234 (6)	0.2500	0.0249 (2)
C1	0.31342 (9)	0.45249 (6)	0.16868 (7)	0.01626 (19)
H1A	0.2919	0.5010	0.1573	0.020*
C2	0.37850 (9)	0.41494 (7)	0.11182 (7)	0.0195 (2)
H2A	0.4017	0.4379	0.0630	0.023*
C3	0.40757 (9)	0.34262 (7)	0.13002 (7)	0.0207 (2)
C4	0.37508 (10)	0.30617 (6)	0.20114 (7)	0.0207 (2)
H4A	0.3955	0.2572	0.2111	0.025*
C5	0.31090 (9)	0.34444 (6)	0.25788 (7)	0.01666 (19)
H5A	0.2883	0.3208	0.3064	0.020*
C6	0.27996 (8)	0.41807 (6)	0.24279 (6)	0.01374 (18)
C7	0.12666 (10)	0.36724 (6)	0.44384 (7)	0.0193 (2)
H7A	0.0583	0.3604	0.4142	0.023*
C8	0.14776 (11)	0.33051 (7)	0.52065 (8)	0.0247 (2)
H8A	0.0940	0.2998	0.5428	0.030*
C9	0.25007 (12)	0.34096 (6)	0.56260 (7)	0.0242 (2)
C10	0.33278 (10)	0.38535 (7)	0.53176 (7)	0.0231 (2)
H10A	0.4018	0.3906	0.5611	0.028*
C11	0.31014 (9)	0.42195 (6)	0.45570 (7)	0.0191 (2)
H11A	0.3647	0.4523	0.4340	0.023*
C12	0.20668 (9)	0.41398 (6)	0.41100 (6)	0.01477 (18)
C13	0.19260 (9)	0.59837 (6)	0.39426 (7)	0.01655 (19)
H13A	0.1238	0.5831	0.4133	0.020*
C14	0.23616 (9)	0.66625 (6)	0.42015 (7)	0.0186 (2)
H14A	0.1979	0.6963	0.4567	0.022*
C15	0.33815 (10)	0.68791 (6)	0.39001 (7)	0.0185 (2)
C16	0.39903 (9)	0.64423 (6)	0.33799 (7)	0.0189 (2)
H16A	0.4679	0.6600	0.3195	0.023*
C17	0.35499 (9)	0.57552 (6)	0.31349 (7)	0.01725 (19)
H17A	0.3957	0.5448	0.2792	0.021*
C18	0.25037 (8)	0.55231 (5)	0.33991 (6)	0.01340 (17)
C37	0.0000	0.57466 (9)	0.2500	0.0235 (3)
C38	0.05647 (9)	0.47660 (6)	0.14043 (7)	0.0185 (2)
C39	0.0000	0.36578 (8)	0.2500	0.0154 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cr1	0.01065 (10)	0.00928 (10)	0.01385 (11)	0.000	0.00032 (7)	0.000
P1	0.01137 (11)	0.01041 (11)	0.01334 (12)	0.00025 (8)	0.00078 (8)	0.00089 (8)
F1	0.0299 (4)	0.0317 (4)	0.0315 (4)	0.0092 (3)	0.0101 (3)	−0.0112 (3)
F2	0.0589 (6)	0.0308 (4)	0.0198 (4)	−0.0033 (4)	−0.0080 (3)	0.0124 (3)
F3	0.0354 (4)	0.0177 (3)	0.0266 (4)	−0.0114 (3)	0.0022 (3)	−0.0056 (3)
O1	0.0433 (8)	0.0133 (6)	0.0749 (12)	0.000	−0.0335 (8)	0.000
O2	0.0223 (4)	0.0483 (6)	0.0196 (4)	−0.0018 (4)	0.0024 (3)	0.0089 (4)
O3	0.0365 (7)	0.0132 (5)	0.0250 (6)	0.000	0.0024 (5)	0.000
C1	0.0154 (4)	0.0155 (4)	0.0180 (5)	0.0012 (4)	0.0019 (4)	0.0001 (4)
C2	0.0173 (5)	0.0231 (5)	0.0185 (5)	0.0001 (4)	0.0042 (4)	−0.0012 (4)
C3	0.0165 (5)	0.0238 (5)	0.0221 (5)	0.0047 (4)	0.0020 (4)	−0.0085 (4)
C4	0.0213 (5)	0.0159 (5)	0.0245 (5)	0.0055 (4)	−0.0024 (4)	−0.0040 (4)
C5	0.0180 (5)	0.0142 (4)	0.0177 (4)	0.0018 (4)	−0.0011 (4)	−0.0002 (4)
C6	0.0121 (4)	0.0134 (4)	0.0156 (4)	0.0010 (3)	−0.0002 (3)	−0.0009 (3)
C7	0.0234 (5)	0.0168 (5)	0.0176 (5)	−0.0029 (4)	0.0008 (4)	0.0021 (4)
C8	0.0360 (6)	0.0184 (5)	0.0199 (5)	−0.0051 (5)	0.0023 (5)	0.0050 (4)
C9	0.0404 (7)	0.0168 (5)	0.0152 (5)	0.0029 (5)	−0.0016 (4)	0.0041 (4)
C10	0.0265 (5)	0.0227 (5)	0.0196 (5)	0.0039 (4)	−0.0050 (4)	0.0024 (4)
C11	0.0185 (5)	0.0204 (5)	0.0183 (5)	0.0009 (4)	−0.0007 (4)	0.0028 (4)
C12	0.0172 (4)	0.0126 (4)	0.0145 (4)	0.0017 (3)	0.0011 (3)	0.0010 (3)
C13	0.0157 (4)	0.0167 (5)	0.0174 (4)	−0.0012 (4)	0.0017 (3)	−0.0009 (4)
C14	0.0212 (5)	0.0167 (5)	0.0180 (5)	−0.0004 (4)	0.0012 (4)	−0.0038 (4)
C15	0.0244 (5)	0.0140 (4)	0.0168 (5)	−0.0054 (4)	−0.0022 (4)	−0.0004 (4)
C16	0.0184 (5)	0.0199 (5)	0.0185 (5)	−0.0062 (4)	0.0012 (4)	0.0004 (4)
C17	0.0157 (5)	0.0168 (5)	0.0194 (5)	−0.0020 (4)	0.0028 (4)	−0.0015 (4)
C18	0.0135 (4)	0.0121 (4)	0.0145 (4)	−0.0006 (3)	−0.0005 (3)	0.0008 (3)
C37	0.0188 (7)	0.0153 (7)	0.0350 (9)	0.000	−0.0117 (6)	0.000
C38	0.0138 (4)	0.0214 (5)	0.0200 (5)	−0.0004 (4)	−0.0013 (4)	0.0044 (4)
C39	0.0167 (6)	0.0159 (6)	0.0138 (6)	0.000	0.0013 (5)	0.000

Geometric parameters (Å, º) top

Cr1—C37	1.8808 (17)	C5—C6	1.4001 (14)
Cr1—C38ⁱ	1.8924 (11)	C5—H5A	0.9300
Cr1—C38	1.8925 (11)	C7—C12	1.3944 (15)
Cr1—C39	1.8989 (15)	C7—C8	1.3972 (15)
Cr1—P1ⁱ	2.3331 (3)	C7—H7A	0.9300
Cr1—P1	2.3331 (3)	C8—C9	1.3744 (19)
P1—C6	1.8288 (10)	C8—H8A	0.9300
P1—C18	1.8391 (10)	C9—C10	1.3796 (18)
P1—C12	1.8414 (10)	C10—C11	1.3886 (15)
F1—C3	1.3587 (12)	C10—H10A	0.9300
F2—C9	1.3570 (13)	C11—C12	1.4005 (15)
F3—C15	1.3595 (12)	C11—H11A	0.9300
O1—C37	1.146 (2)	C13—C14	1.3880 (15)
O2—C38	1.1471 (15)	C13—C18	1.4020 (14)
O3—C39	1.1481 (19)	C13—H13A	0.9300
C1—C2	1.3931 (15)	C14—C15	1.3846 (16)
C1—C6	1.4023 (14)	C14—H14A	0.9300
C1—H1A	0.9300	C15—C16	1.3737 (16)
C2—C3	1.3806 (16)	C16—C17	1.3973 (15)
C2—H2A	0.9300	C16—H16A	0.9300
C3—C4	1.3758 (17)	C17—C18	1.3998 (14)
C4—C5	1.3918 (15)	C17—H17A	0.9300
C4—H4A	0.9300

C37—Cr1—C38ⁱ	86.78 (3)	C12—C7—C8	120.96 (11)
C37—Cr1—C38	86.78 (3)	C12—C7—H7A	119.5
C38ⁱ—Cr1—C38	173.56 (7)	C8—C7—H7A	119.5
C37—Cr1—C39	180.0	C9—C8—C7	118.26 (11)
C38ⁱ—Cr1—C39	93.22 (3)	C9—C8—H8A	120.9
C38—Cr1—C39	93.22 (3)	C7—C8—H8A	120.9
C37—Cr1—P1ⁱ	92.850 (8)	F2—C9—C8	119.05 (11)
C38ⁱ—Cr1—P1ⁱ	90.85 (3)	F2—C9—C10	118.04 (11)
C38—Cr1—P1ⁱ	89.47 (3)	C8—C9—C10	122.90 (11)
C39—Cr1—P1ⁱ	87.150 (8)	C9—C10—C11	118.12 (11)
C37—Cr1—P1	92.851 (8)	C9—C10—H10A	120.9
C38ⁱ—Cr1—P1	89.47 (3)	C11—C10—H10A	120.9
C38—Cr1—P1	90.85 (3)	C10—C11—C12	121.24 (11)
C39—Cr1—P1	87.149 (8)	C10—C11—H11A	119.4
P1ⁱ—Cr1—P1	174.299 (16)	C12—C11—H11A	119.4
C6—P1—C18	104.74 (5)	C7—C12—C11	118.50 (10)
C6—P1—C12	101.46 (5)	C7—C12—P1	122.43 (8)
C18—P1—C12	99.22 (5)	C11—C12—P1	119.07 (8)
C6—P1—Cr1	112.95 (3)	C14—C13—C18	121.25 (10)
C18—P1—Cr1	117.00 (3)	C14—C13—H13A	119.4
C12—P1—Cr1	119.17 (3)	C18—C13—H13A	119.4
C2—C1—C6	120.85 (10)	C15—C14—C13	118.16 (10)
C2—C1—H1A	119.6	C15—C14—H14A	120.9
C6—C1—H1A	119.6	C13—C14—H14A	120.9
C3—C2—C1	118.03 (10)	F3—C15—C16	118.55 (10)
C3—C2—H2A	121.0	F3—C15—C14	118.63 (10)
C1—C2—H2A	121.0	C16—C15—C14	122.81 (10)
F1—C3—C4	118.64 (10)	C15—C16—C17	118.40 (10)
F1—C3—C2	118.19 (11)	C15—C16—H16A	120.8
C4—C3—C2	123.17 (10)	C17—C16—H16A	120.8
C3—C4—C5	118.30 (10)	C16—C17—C18	120.86 (10)
C3—C4—H4A	120.9	C16—C17—H17A	119.6
C5—C4—H4A	120.9	C18—C17—H17A	119.6
C4—C5—C6	120.81 (10)	C17—C18—C13	118.45 (9)
C4—C5—H5A	119.6	C17—C18—P1	125.23 (8)
C6—C5—H5A	119.6	C13—C18—P1	116.31 (8)
C5—C6—C1	118.82 (9)	O1—C37—Cr1	180.0
C5—C6—P1	120.41 (8)	O2—C38—Cr1	177.10 (11)
C1—C6—P1	120.24 (8)	O3—C39—Cr1	180.0

C37—Cr1—P1—C6	−118.45 (4)	C7—C8—C9—C10	−0.71 (19)
C38ⁱ—Cr1—P1—C6	154.80 (5)	F2—C9—C10—C11	−178.90 (11)
C38—Cr1—P1—C6	−31.63 (5)	C8—C9—C10—C11	1.24 (19)
C39—Cr1—P1—C6	61.55 (4)	C9—C10—C11—C12	−0.34 (18)
C37—Cr1—P1—C18	3.27 (4)	C8—C7—C12—C11	1.58 (17)
C38ⁱ—Cr1—P1—C18	−83.48 (5)	C8—C7—C12—P1	−179.28 (9)
C38—Cr1—P1—C18	90.09 (5)	C10—C11—C12—C7	−1.03 (17)
C39—Cr1—P1—C18	−176.73 (4)	C10—C11—C12—P1	179.80 (9)
C37—Cr1—P1—C12	122.64 (4)	C6—P1—C12—C7	−111.54 (9)
C38ⁱ—Cr1—P1—C12	35.89 (5)	C18—P1—C12—C7	141.25 (9)
C38—Cr1—P1—C12	−150.55 (5)	Cr1—P1—C12—C7	13.13 (10)
C39—Cr1—P1—C12	−57.36 (4)	C6—P1—C12—C11	67.60 (9)
C6—C1—C2—C3	0.94 (16)	C18—P1—C12—C11	−39.61 (9)
C1—C2—C3—F1	179.61 (10)	Cr1—P1—C12—C11	−167.73 (7)
C1—C2—C3—C4	0.20 (17)	C18—C13—C14—C15	0.74 (16)
F1—C3—C4—C5	179.83 (10)	C13—C14—C15—F3	177.88 (10)
C2—C3—C4—C5	−0.76 (18)	C13—C14—C15—C16	−2.03 (17)
C3—C4—C5—C6	0.18 (16)	F3—C15—C16—C17	−178.85 (10)
C4—C5—C6—C1	0.92 (16)	C14—C15—C16—C17	1.06 (17)
C4—C5—C6—P1	172.56 (8)	C15—C16—C17—C18	1.22 (16)
C2—C1—C6—C5	−1.49 (16)	C16—C17—C18—C13	−2.42 (16)
C2—C1—C6—P1	−173.15 (8)	C16—C17—C18—P1	178.79 (8)
C18—P1—C6—C5	130.53 (8)	C14—C13—C18—C17	1.42 (16)
C12—P1—C6—C5	27.68 (9)	C14—C13—C18—P1	−179.68 (8)
Cr1—P1—C6—C5	−101.07 (8)	C6—P1—C18—C17	0.15 (10)
C18—P1—C6—C1	−57.95 (9)	C12—P1—C18—C17	104.68 (9)
C12—P1—C6—C1	−160.80 (8)	Cr1—P1—C18—C17	−125.76 (8)
Cr1—P1—C6—C1	70.45 (9)	C6—P1—C18—C13	−178.66 (8)
C12—C7—C8—C9	−0.74 (18)	C12—P1—C18—C13	−74.13 (9)
C7—C8—C9—F2	179.43 (11)	Cr1—P1—C18—C13	55.42 (9)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···O1ⁱⁱ	0.93	2.55	3.4602 (16)	165
C8—H8A···F1ⁱⁱⁱ	0.93	2.48	3.3830 (16)	165
C14—H14A···F3^iv	0.93	2.46	3.3561 (14)	161

Symmetry codes: (ii) x+1/2, y−1/2, z; (iii) x−1/2, −y+1/2, z+1/2; (iv) −x+1/2, −y+3/2, −z+1.

Experimental details

Crystal data
Chemical formula	[Cr(C₁₈H₁₂F₃P)₂(CO)₄]
M_r	796.53
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	11.9318 (8), 18.0956 (8), 15.8195 (8)
β (°)	92.740 (1)
V (Å³)	3411.7 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.51
Crystal size (mm)	0.29 × 0.21 × 0.19

Data collection
Diffractometer	Bruker APEX Duo CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.869, 0.912
No. of measured, independent and observed [I > 2σ(I)] reflections	35263, 5028, 4627
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.705

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.074, 1.04
No. of reflections	5028
No. of parameters	242
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.47

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

Selected bond lengths (Å) top

Cr1—C37	1.8808 (17)	Cr1—C39	1.8989 (15)
Cr1—C38ⁱ	1.8924 (11)	Cr1—P1ⁱ	2.3331 (3)
Cr1—C38	1.8925 (11)	Cr1—P1	2.3331 (3)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···O1ⁱⁱ	0.9300	2.5500	3.4602 (16)	165.00
C8—H8A···F1ⁱⁱⁱ	0.9300	2.4800	3.3830 (16)	165.00
C14—H14A···F3^iv	0.9300	2.4600	3.3561 (14)	161.00

Symmetry codes: (ii) x+1/2, y−1/2, z; (iii) x−1/2, −y+1/2, z+1/2; (iv) −x+1/2, −y+3/2, −z+1.

Footnotes

‡Thomson Reuters Researcher ID: D-6198-2011

§Additional correspondence author: omarsa@usm.my. Thomson Reuters Researcher ID: B-6034-2009

¶Thomson Reuters ResearcherID: A-3561-2009

Acknowledgements

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

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