Tricarbon­yl(η6-4′,7-dimethoxy­iso­flavone)chromium(0)

Tonder, J.H. van; Bezuidenhoudt, B.C.B.; Janse van Rensburg, J.M.

doi:10.1107/S1600536809040537

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page m1343

https://doi.org/10.1107/S1600536809040537

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Tricarbonyl(η⁶-4′,7-dimethoxyisoflavone)chromium(0)

Johannes H. van Tonder,^a Barend C. B. Bezuidenhoudt ^a ^* and J. Marthinus Janse van Rensburg ^b

^aDepartment of Chemistry, University of the Free State, PO Box 339, Bloemfontein 9300, South Africa, and ^bDepartment of Pharmacology, University of Pretoria, PO Box 2034, Pretoria 0001, South Africa
^*Correspondence e-mail: bezuidbc.sci@ufs.ac.za

(Received 30 September 2009; accepted 5 October 2009; online 10 October 2009)

The metal atom of the Cr(CO)₃ unit of the title compound, [Cr(C₁₇H₁₄O₄)(CO)₃], is coordinated to the methoxyphenyl ring of the isoflavone ligand; the Cr(CO)₃ unit exhibits a three-legged piano-stool conformation. The aromatic ring of the methoxyphenyl group is twisted by 42.49 (9)° with respect to the γ-pyrone ring. In the fused-ring, the dihedral angle between the phenylene and γ-pyrone rings is 3.08 (13)°.

Related literature

For tricarbonyl(arene)chromium complexes in regioselective reactions, see: Dominique et al. (1999 ). For their photochromic properties, see: Hannesschlager et al. (1999 ). For Cr(CO)₃ complexation to the aromatic ring of flavanone, see: Dominique et al. (1999). For Cr(CO)₃ complexation to (1,3-dimethoxybenzene), see: Zeller et al. (2004 ). For comparison bond distances, see: Allen (2002 ). For the synthesis of 4′,7-dimethoxyisoflavone, see: Thakkar & Cushman (1995 ).

Experimental

Crystal data

[Cr(C₁₇H₁₄O₄)(CO)₃]
M_r = 418.31
Monoclinic, P 2₁ /c
a = 12.3454 (7) Å
b = 17.9984 (8) Å
c = 7.9988 (4) Å
β = 103.733 (2)°
V = 1726.50 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.71 mm⁻¹
T = 173 K
0.43 × 0.23 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.751, T_max = 0.933
9320 measured reflections
4145 independent reflections
3393 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.117
S = 1.08
4145 reflections
255 parameters
H-atom parameters constrained
Δρ_max = 0.86 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536809040537/ng2656sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809040537/ng2656Isup2.hkl

checkCIF report

Comment top

Tricarbonyl(arene)chromium complexes have recieved much attention due to their use as intermediates in regioselective reactions (Dominique et al., 1999), as well as for their photochromic properties (Hannesschlager et al., 1999).

The title compound, (I), [Cr(CO)₃(C₁₇H₁₄O₄)], where (C₁₇H₁₄O₄) = 4',7-dimethoxyisoflavone, crystallized in the monoclinic space group P2₁/c, with Z = 4 (Fig.1). For the title compound the molecular structure displays the Cr(CO)₃ moiety complexation to the phenyl ring, exhibiting the known three-legged piano-stool conformation. This conformation is expected for a tricarbonyl-metal with an η⁶-coordinated arene. The Cr—C(arene) distances range from 2.188 (2) to 2.262 (2) Å. The longest Cr—C(arene) bond is Cr—C4', that in turn is bonded to the O4'—C41' methoxy group. This bond elongation is probably due to the methoxy group that weakens the π-interaction ability of C4' towards the chromium metal centre. The Cr-arene(centroid) distance is 1.7205 (4) Å. The Cr—C(carbonyl) bond distances range from 1.827 (3) to 1.855 (3) Å and the carbonyl distances of C11—O1, C12—O2 and C13—O3 are 1.158 (3), 1.154 (3) and 1.150 (3) Å respectively. These distances are within the normal range, see Allen (2002). The phenyl ring is essentialy planar (r.m.s of fitted atoms C1'-C6' = 0.0119 Å). Slight molecular disorder is displayed by a twist in the isoflavone backbone, that forms a dihedral angle of 42.49 (9)° between the phenyl and γ-pyrone ring and a dihedral angle of 41.1 (1)° between the phenyl and the benzopyrone ring system. A dihedral angle of 3.08 (13)° is also present between the benzene and the γ-pyrone ring, with a r.m.s of fitted atoms C2—C10 and O5 of 0.0387 Å. The O4'—C41' methoxy group on the phenyl ring bends towards the Cr(CO)₃ moiety, forming the C5'-C4'-O4'-C41' tortion angle of 15.9 (4)°. The O7—C71 methoxy group on the benzene ring is also slightly displaced from the benzene ring plane, shown by the C8—C7—O7—C71 tortion angle of 175.0 (3)°. Other molecular geometrical parameters is in good agreement with literature values, see Allen (2002). Selected geometrical parameters is presented in Table 1.

As illustrated in Fig.2 the molecular packing is such that a benzene ring of one molecule is above the γ-pyrone ring of a neighbouring molecule, separated by a plane to plane distance of 3.369 Å and a centroid to centroid distance of 4.281 Å.

Related literature top

For tricarbonyl(arene)chromium complexes in regioselective reactions, see: Dominique et al. (1999). For their photochromic properties, see: Hannesschlager et al. (1999). For Cr(CO)₃ complexation to the aromatic ring of flavanone, see: Dominique et al. (1999). For Cr(CO)₃ complexation to (1,3-dimethoxybenzene), see: Zeller et al. (2004). For comparison bond distances, see: Allen (2002). For the synthesis of 4',7-dimethoxyisoflavone, see: Thakkar & Cushman (1995).

Experimental top

4',7-Dimethoxyisoflavone was prepared as previously described by Thakkar & Cushman (1995). A solution of 4',7-Dimethoxyisoflavone (1.28 g, 4.5 mmol) and Cr(CO)₆ (1.00 g, 4.6 mmol: 1 eq.) in Bu₂O:THF (9:1; 10 ml per 100 mg Cr(CO)₆ was degassed with argon, using standard Schlenk techniques, and refluxed (48 h) under an oxygen free atmosphere. The reaction mixture was cooled to room temperature and the solvent evaporated in vacuo. Purification through flash column-chromatography yielded tricarbonyl(B-η⁶-4',7-dimethoxyisoflavone)-chromium(0) (0.48 g; 25.0%) as a yellow solid. Recrystallization from diethyl ether yielded yellow cuboidal crystals.

R_f 0.18 (Hexane: Acetone; 8:2); Mp 127.0 °C; Note: A, B and C-ring labelling refers to the benzene, phenyl and γ-pyrone rings respectively. ¹H NMR (600 MHz, CDCl₃) δ p.p.m. 8.15 (1H, d, J = 9.04 Hz, H-5), 8.09 (1H, s, H-2), 7.01 (1H, dd, J = 1.88, 9.04 Hz, H-6), 6.86 (1H, d, J = 1.88 Hz, H-8), 5.85 (2H, d, J = 6.78 Hz, H-2' and H-6'), 5.21 (2H, d, J = 6.78 Hz, H-3' and H-5'), 3.92 (3H, s, –OCH₃), 3.75 (3H, s, –OCH₃); ¹³C NMR (151 MHz, CDCl₃) δ p.p.m. 55.88 (–OCH₃), 56.06 (–OCH₃), 77.37 (C-3' and C-5'), 94.71, 97.63 (C-2' and C-6'), 100.45 (C-8), 115.32 (C-6), 117.67, 121.16, 127.71 (C-5), 143.39 (C(i)-OCH₃ B-ring), 154.78 (C-2), 158.07, 164.60, 175.26 (C-4), 232.89 (Cr—CO); MS (MS Scheme 3) m/z 362 (M⁺-2CO, 0.5%), 343 (2.1), 282 (100.0), 267 (20.8), 252 (3.0), 239 (10.9), 224 (3.7), 211 (3.8), 196 (3.5), 183 (1.2), 168 (2.9), 150 (12.9), 141 (6.1), 131 (69.5), 122 (10.7), 107 (7.9), 103 (2.4).

Structure description top

For tricarbonyl(arene)chromium complexes in regioselective reactions, see: Dominique et al. (1999). For their photochromic properties, see: Hannesschlager et al. (1999). For Cr(CO)₃ complexation to the aromatic ring of flavanone, see: Dominique et al. (1999). For Cr(CO)₃ complexation to (1,3-dimethoxybenzene), see: Zeller et al. (2004). For comparison bond distances, see: Allen (2002). For the synthesis of 4',7-dimethoxyisoflavone, see: Thakkar & Cushman (1995).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus (Bruker, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. A view of (I) showing the atom-numbering scheme with displacement ellipsoids at the 30% probability level.
	Fig. 2. Indication of molecular packing in the unit-cell. Symmetry operators 1) x; y; z. 2) x; 0.5 - y; -1/2 + z. 3) 1 - x; 1/2 + y; 1.5 - z. 4) 1 - x; 1 - y; 1 - z.

Tricarbonyl(η⁶-4',7-dimethoxyisoflavone)chromium(0) top

Crystal data top

[Cr(C₁₇H₁₄O₄)(CO)₃]	F(000) = 856
M_r = 418.31	D_x = 1.609 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3261 reflections
a = 12.3454 (7) Å	θ = 2.8–28.3°
b = 17.9984 (8) Å	µ = 0.71 mm⁻¹
c = 7.9988 (4) Å	T = 173 K
β = 103.733 (2)°	Block, yellow
V = 1726.50 (15) Å³	0.43 × 0.23 × 0.1 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	4145 independent reflections
Radiation source: fine-focus sealed tube	3393 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
φ and ω scans	θ_max = 28°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −16→9
T_min = 0.751, T_max = 0.933	k = −23→21
9320 measured reflections	l = −10→9

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.044	w = 1/[σ²(F_o²) + (0.0453P)² + 2.2801P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.117	(Δ/σ)_max < 0.001
S = 1.08	Δρ_max = 0.86 e Å⁻³
4145 reflections	Δρ_min = −0.41 e Å⁻³
255 parameters

Crystal data top

[Cr(C₁₇H₁₄O₄)(CO)₃]	V = 1726.50 (15) Å³
M_r = 418.31	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.3454 (7) Å	µ = 0.71 mm⁻¹
b = 17.9984 (8) Å	T = 173 K
c = 7.9988 (4) Å	0.43 × 0.23 × 0.1 mm
β = 103.733 (2)°

Data collection top

Bruker APEXII CCD diffractometer	4145 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	3393 reflections with I > 2σ(I)
T_min = 0.751, T_max = 0.933	R_int = 0.027
9320 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.117	H-atom parameters constrained
S = 1.08	Δρ_max = 0.86 e Å⁻³
4145 reflections	Δρ_min = −0.41 e Å⁻³
255 parameters

Special details top

Experimental. The intensity data was collected on a Bruker Apex II CCD diffractometer using an exposure time of 10 s/frame. The 509 frames were collected with a frame width of 0.5° covering up to θ = 28° with 99.4% completeness accomplished.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cr	0.67866 (3)	0.08506 (2)	0.83271 (5)	0.01520 (12)
C71	−0.0137 (3)	0.34474 (18)	0.1743 (5)	0.0415 (8)
H71A	−0.0177	0.3606	0.29	0.062*
H71B	−0.0845	0.3559	0.0926	0.062*
H71C	0.0469	0.3713	0.1402	0.062*
C1'	0.5514 (2)	0.16695 (13)	0.8698 (3)	0.0170 (5)
C2	0.4317 (2)	0.26583 (14)	0.7185 (3)	0.0210 (5)
H2	0.4859	0.2986	0.7838	0.025*
C2'	0.6553 (2)	0.20306 (14)	0.8800 (3)	0.0198 (5)
H2'	0.6591	0.2432	0.8046	0.024*
C3'	0.7524 (2)	0.18039 (14)	0.9997 (3)	0.0212 (5)
H3'	0.8208	0.2058	1.0066	0.025*
C3	0.4495 (2)	0.19286 (14)	0.7448 (3)	0.0185 (5)
C4	0.3661 (2)	0.13983 (14)	0.6510 (3)	0.0192 (5)
C4'	0.7479 (2)	0.11970 (14)	1.1093 (3)	0.0201 (5)
C5	0.1963 (2)	0.13098 (15)	0.4082 (4)	0.0248 (6)
H5	0.2022	0.0784	0.4126	0.03*
C5'	0.6471 (2)	0.08121 (14)	1.0971 (3)	0.0182 (5)
H5'	0.6442	0.0395	1.1688	0.022*
C6	0.1094 (2)	0.16347 (16)	0.2927 (4)	0.0272 (6)
H6	0.0567	0.1336	0.2156	0.033*
C6'	0.5506 (2)	0.10521 (14)	0.9775 (3)	0.0185 (5)
H6'	0.4828	0.0789	0.9692	0.022*
C7	0.0986 (2)	0.24107 (16)	0.2887 (4)	0.0246 (6)
C8	0.1774 (2)	0.28543 (15)	0.3938 (4)	0.0241 (6)
H8	0.1713	0.338	0.3893	0.029*
C9	0.2667 (2)	0.25058 (14)	0.5070 (3)	0.0196 (5)
C10	0.2769 (2)	0.17415 (14)	0.5204 (3)	0.0196 (5)
C11	0.6772 (2)	0.11149 (14)	0.6116 (4)	0.0224 (5)
C12	0.8108 (2)	0.03640 (15)	0.8470 (4)	0.0252 (6)
C13	0.6030 (2)	−0.00087 (14)	0.7453 (3)	0.0213 (5)
C41'	0.8552 (3)	0.03005 (17)	1.2974 (4)	0.0326 (7)
H41A	0.8072	0.0277	1.3788	0.049*
H41B	0.9328	0.0212	1.3587	0.049*
H41C	0.8319	−0.0079	1.2082	0.049*
O1	0.6770 (2)	0.12958 (12)	0.4726 (3)	0.0362 (5)
O2	0.89489 (18)	0.00706 (14)	0.8540 (3)	0.0461 (6)
O3	0.55781 (18)	−0.05454 (11)	0.6900 (3)	0.0318 (5)
O4'	0.84603 (16)	0.10203 (11)	1.2190 (2)	0.0260 (4)
O4	0.36907 (17)	0.07292 (10)	0.6784 (3)	0.0271 (4)
O5	0.34364 (15)	0.29706 (10)	0.6077 (2)	0.0227 (4)
O7	0.00685 (17)	0.26705 (12)	0.1746 (3)	0.0347 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cr	0.0162 (2)	0.01354 (19)	0.0156 (2)	−0.00044 (15)	0.00332 (14)	0.00014 (15)
C71	0.0309 (16)	0.0381 (18)	0.050 (2)	0.0135 (14)	−0.0004 (15)	0.0107 (15)
C1'	0.0199 (12)	0.0159 (11)	0.0154 (11)	0.0018 (9)	0.0048 (9)	−0.0032 (9)
C2	0.0205 (12)	0.0201 (12)	0.0211 (12)	0.0020 (10)	0.0024 (10)	0.0009 (10)
C2'	0.0242 (13)	0.0139 (11)	0.0208 (12)	−0.0011 (9)	0.0047 (10)	−0.0009 (9)
C3'	0.0204 (12)	0.0188 (12)	0.0228 (13)	−0.0029 (10)	0.0020 (10)	−0.0026 (10)
C3	0.0185 (12)	0.0199 (12)	0.0177 (12)	0.0012 (9)	0.0058 (10)	0.0018 (10)
C4	0.0187 (12)	0.0188 (12)	0.0203 (12)	0.0014 (9)	0.0054 (10)	0.0015 (10)
C4'	0.0218 (12)	0.0192 (12)	0.0173 (12)	0.0002 (10)	0.0007 (10)	−0.0037 (10)
C5	0.0249 (13)	0.0200 (13)	0.0277 (14)	−0.0016 (10)	0.0028 (11)	0.0021 (11)
C5'	0.0272 (13)	0.0156 (11)	0.0124 (11)	0.0003 (10)	0.0060 (9)	0.0014 (9)
C6	0.0227 (13)	0.0291 (14)	0.0268 (14)	−0.0044 (11)	0.0002 (11)	0.0029 (12)
C6'	0.0191 (12)	0.0193 (12)	0.0179 (12)	−0.0008 (9)	0.0059 (10)	−0.0012 (9)
C7	0.0173 (12)	0.0293 (14)	0.0269 (14)	0.0042 (10)	0.0049 (10)	0.0086 (11)
C8	0.0241 (13)	0.0209 (13)	0.0268 (14)	0.0044 (10)	0.0049 (11)	0.0062 (11)
C9	0.0187 (12)	0.0215 (12)	0.0190 (12)	0.0012 (10)	0.0051 (10)	0.0006 (10)
C10	0.0187 (12)	0.0198 (12)	0.0209 (12)	0.0004 (9)	0.0056 (10)	0.0027 (10)
C11	0.0237 (13)	0.0178 (12)	0.0247 (14)	−0.0014 (10)	0.0038 (10)	−0.0025 (10)
C12	0.0245 (13)	0.0227 (13)	0.0260 (14)	0.0002 (11)	0.0013 (11)	−0.0061 (11)
C13	0.0242 (13)	0.0210 (13)	0.0199 (12)	−0.0013 (10)	0.0073 (10)	0.0001 (10)
C41'	0.0289 (15)	0.0312 (15)	0.0324 (16)	0.0028 (12)	−0.0033 (12)	0.0096 (13)
O1	0.0576 (15)	0.0321 (11)	0.0212 (10)	−0.0032 (10)	0.0140 (10)	0.0037 (9)
O2	0.0268 (12)	0.0449 (14)	0.0615 (16)	0.0122 (10)	0.0002 (11)	−0.0138 (12)
O3	0.0364 (12)	0.0229 (10)	0.0373 (12)	−0.0090 (9)	0.0110 (9)	−0.0063 (9)
O4'	0.0216 (9)	0.0258 (10)	0.0255 (10)	−0.0009 (7)	−0.0041 (8)	0.0029 (8)
O4	0.0275 (10)	0.0177 (9)	0.0312 (11)	−0.0030 (7)	−0.0030 (8)	0.0048 (8)
O5	0.0232 (9)	0.0172 (9)	0.0253 (10)	0.0024 (7)	0.0009 (8)	0.0008 (7)
O7	0.0233 (10)	0.0340 (12)	0.0410 (13)	0.0039 (8)	−0.0038 (9)	0.0103 (10)

Geometric parameters (Å, º) top

Cr—C11	1.827 (3)	C4—C10	1.463 (3)
Cr—C12	1.831 (3)	C4'—O4'	1.354 (3)
Cr—C13	1.855 (3)	C4'—C5'	1.407 (4)
Cr—C2'	2.188 (2)	C5—C6	1.369 (4)
Cr—C6'	2.200 (2)	C5—C10	1.405 (4)
Cr—C1'	2.225 (2)	C5—H5	0.95
Cr—C3'	2.231 (3)	C5'—C6'	1.407 (3)
Cr—C5'	2.241 (2)	C5'—H5'	0.95
Cr—C4'	2.262 (2)	C6—C7	1.403 (4)
C71—O7	1.421 (4)	C6—H6	0.95
C71—H71A	0.98	C6'—H6'	0.95
C71—H71B	0.98	C7—O7	1.358 (3)
C71—H71C	0.98	C7—C8	1.379 (4)
C1'—C6'	1.407 (3)	C8—C9	1.398 (4)
C1'—C2'	1.423 (3)	C8—H8	0.95
C1'—C3	1.484 (3)	C9—O5	1.374 (3)
C2—C3	1.340 (4)	C9—C10	1.383 (4)
C2—O5	1.351 (3)	C11—O1	1.158 (3)
C2—H2	0.95	C12—O2	1.154 (3)
C2'—C3'	1.406 (4)	C13—O3	1.150 (3)
C2'—H2'	0.95	C41'—O4'	1.432 (3)
C3'—C4'	1.410 (4)	C41'—H41A	0.98
C3'—H3'	0.95	C41'—H41B	0.98
C3—C4	1.472 (3)	C41'—H41C	0.98
C4—O4	1.223 (3)

C11—Cr—C12	89.38 (12)	C4'—C3'—Cr	72.89 (14)
C11—Cr—C13	87.92 (12)	C2'—C3'—H3'	120.2
C12—Cr—C13	89.19 (12)	C4'—C3'—H3'	120.2
C11—Cr—C2'	86.74 (11)	Cr—C3'—H3'	129.5
C12—Cr—C2'	127.26 (11)	C2—C3—C4	119.1 (2)
C13—Cr—C2'	143.03 (11)	C2—C3—C1'	119.7 (2)
C11—Cr—C6'	128.55 (11)	C4—C3—C1'	121.2 (2)
C12—Cr—C6'	141.88 (11)	O4—C4—C10	121.9 (2)
C13—Cr—C6'	88.62 (10)	O4—C4—C3	124.0 (2)
C2'—Cr—C6'	66.94 (10)	C10—C4—C3	114.0 (2)
C11—Cr—C1'	96.39 (11)	O4'—C4'—C5'	124.7 (2)
C12—Cr—C1'	162.83 (11)	O4'—C4'—C3'	115.1 (2)
C13—Cr—C1'	107.12 (10)	C5'—C4'—C3'	120.2 (2)
C2'—Cr—C1'	37.61 (9)	O4'—C4'—Cr	129.89 (18)
C6'—Cr—C1'	37.09 (9)	C5'—C4'—Cr	70.96 (14)
C11—Cr—C3'	106.73 (11)	C3'—C4'—Cr	70.53 (15)
C12—Cr—C3'	95.71 (11)	C6—C5—C10	121.1 (3)
C13—Cr—C3'	164.55 (11)	C6—C5—H5	119.4
C2'—Cr—C3'	37.07 (9)	C10—C5—H5	119.4
C6'—Cr—C3'	78.48 (10)	C6'—C5'—C4'	119.2 (2)
C1'—Cr—C3'	67.15 (9)	C6'—C5'—Cr	69.97 (14)
C11—Cr—C5'	163.24 (11)	C4'—C5'—Cr	72.62 (14)
C12—Cr—C5'	106.15 (11)	C6'—C5'—H5'	120.4
C13—Cr—C5'	98.36 (10)	C4'—C5'—H5'	120.4
C2'—Cr—C5'	78.88 (9)	Cr—C5'—H5'	129.3
C6'—Cr—C5'	36.93 (9)	C5—C6—C7	119.7 (3)
C1'—Cr—C5'	66.93 (9)	C5—C6—H6	120.2
C3'—Cr—C5'	66.21 (9)	C7—C6—H6	120.2
C11—Cr—C4'	142.14 (11)	C5'—C6'—C1'	122.1 (2)
C12—Cr—C4'	86.93 (11)	C5'—C6'—Cr	73.10 (14)
C13—Cr—C4'	129.64 (11)	C1'—C6'—Cr	72.42 (14)
C2'—Cr—C4'	66.30 (9)	C5'—C6'—H6'	119
C6'—Cr—C4'	65.90 (9)	C1'—C6'—H6'	119
C1'—Cr—C4'	78.58 (9)	Cr—C6'—H6'	127.7
C3'—Cr—C4'	36.57 (9)	O7—C7—C8	124.4 (3)
C5'—Cr—C4'	36.43 (9)	O7—C7—C6	114.7 (3)
O7—C71—H71A	109.5	C8—C7—C6	120.9 (2)
O7—C71—H71B	109.5	C7—C8—C9	117.9 (2)
H71A—C71—H71B	109.5	C7—C8—H8	121
O7—C71—H71C	109.5	C9—C8—H8	121
H71A—C71—H71C	109.5	O5—C9—C10	121.5 (2)
H71B—C71—H71C	109.5	O5—C9—C8	115.8 (2)
C6'—C1'—C2'	117.5 (2)	C10—C9—C8	122.7 (2)
C6'—C1'—C3	122.2 (2)	C9—C10—C5	117.6 (2)
C2'—C1'—C3	120.2 (2)	C9—C10—C4	121.0 (2)
C6'—C1'—Cr	70.49 (14)	C5—C10—C4	121.4 (2)
C2'—C1'—Cr	69.80 (14)	O1—C11—Cr	178.7 (2)
C3—C1'—Cr	129.11 (17)	O2—C12—Cr	178.4 (3)
C3—C2—O5	126.0 (2)	O3—C13—Cr	178.8 (2)
C3—C2—H2	117	O4'—C41'—H41A	109.5
O5—C2—H2	117	O4'—C41'—H41B	109.5
C3'—C2'—C1'	121.2 (2)	H41A—C41'—H41B	109.5
C3'—C2'—Cr	73.13 (15)	O4'—C41'—H41C	109.5
C1'—C2'—Cr	72.59 (14)	H41A—C41'—H41C	109.5
C3'—C2'—H2'	119.4	H41B—C41'—H41C	109.5
C1'—C2'—H2'	119.4	C4'—O4'—C41'	117.5 (2)
Cr—C2'—H2'	126.9	C2—O5—C9	117.9 (2)
C2'—C3'—C4'	119.7 (2)	C7—O7—C71	117.4 (2)
C2'—C3'—Cr	69.80 (14)

C11—Cr—C1'—C6'	153.08 (16)	C5'—Cr—C4'—O4'	119.8 (3)
C12—Cr—C1'—C6'	−97.9 (4)	C11—Cr—C4'—C5'	152.16 (18)
C13—Cr—C1'—C6'	63.30 (16)	C12—Cr—C4'—C5'	−122.82 (17)
C2'—Cr—C1'—C6'	−130.8 (2)	C13—Cr—C4'—C5'	−36.4 (2)
C3'—Cr—C1'—C6'	−101.42 (16)	C2'—Cr—C4'—C5'	103.89 (16)
C5'—Cr—C1'—C6'	−28.66 (14)	C6'—Cr—C4'—C5'	29.69 (14)
C4'—Cr—C1'—C6'	−64.94 (15)	C1'—Cr—C4'—C5'	66.45 (15)
C11—Cr—C1'—C2'	−76.17 (16)	C3'—Cr—C4'—C5'	133.3 (2)
C12—Cr—C1'—C2'	32.8 (4)	C11—Cr—C4'—C3'	18.8 (2)
C13—Cr—C1'—C2'	−165.95 (15)	C12—Cr—C4'—C3'	103.85 (17)
C6'—Cr—C1'—C2'	130.8 (2)	C13—Cr—C4'—C3'	−169.74 (16)
C3'—Cr—C1'—C2'	29.33 (15)	C2'—Cr—C4'—C3'	−29.44 (15)
C5'—Cr—C1'—C2'	102.09 (16)	C6'—Cr—C4'—C3'	−103.64 (17)
C4'—Cr—C1'—C2'	65.82 (15)	C1'—Cr—C4'—C3'	−66.88 (16)
C11—Cr—C1'—C3	36.9 (2)	C5'—Cr—C4'—C3'	−133.3 (2)
C12—Cr—C1'—C3	145.9 (4)	O4'—C4'—C5'—C6'	−180.0 (2)
C13—Cr—C1'—C3	−52.9 (2)	C3'—C4'—C5'—C6'	−1.6 (4)
C2'—Cr—C1'—C3	113.1 (3)	Cr—C4'—C5'—C6'	−54.1 (2)
C6'—Cr—C1'—C3	−116.1 (3)	O4'—C4'—C5'—Cr	−125.9 (3)
C3'—Cr—C1'—C3	142.4 (2)	C3'—C4'—C5'—Cr	52.5 (2)
C5'—Cr—C1'—C3	−144.8 (2)	C11—Cr—C5'—C6'	34.8 (4)
C4'—Cr—C1'—C3	178.9 (2)	C12—Cr—C5'—C6'	−167.93 (16)
C6'—C1'—C2'—C3'	−3.3 (4)	C13—Cr—C5'—C6'	−76.34 (16)
C3—C1'—C2'—C3'	178.8 (2)	C2'—Cr—C5'—C6'	66.23 (15)
Cr—C1'—C2'—C3'	−56.9 (2)	C1'—Cr—C5'—C6'	28.78 (14)
C6'—C1'—C2'—Cr	53.6 (2)	C3'—Cr—C5'—C6'	102.91 (16)
C3—C1'—C2'—Cr	−124.3 (2)	C4'—Cr—C5'—C6'	131.2 (2)
C11—Cr—C2'—C3'	−123.62 (17)	C11—Cr—C5'—C4'	−96.4 (4)
C12—Cr—C2'—C3'	−36.9 (2)	C12—Cr—C5'—C4'	60.89 (17)
C13—Cr—C2'—C3'	154.20 (18)	C13—Cr—C5'—C4'	152.48 (16)
C6'—Cr—C2'—C3'	101.74 (17)	C2'—Cr—C5'—C4'	−64.95 (15)
C1'—Cr—C2'—C3'	131.5 (2)	C6'—Cr—C5'—C4'	−131.2 (2)
C5'—Cr—C2'—C3'	65.04 (16)	C1'—Cr—C5'—C4'	−102.40 (16)
C4'—Cr—C2'—C3'	29.07 (15)	C3'—Cr—C5'—C4'	−28.27 (14)
C11—Cr—C2'—C1'	104.87 (16)	C10—C5—C6—C7	−1.7 (4)
C12—Cr—C2'—C1'	−168.40 (16)	C4'—C5'—C6'—C1'	−0.4 (4)
C13—Cr—C2'—C1'	22.7 (2)	Cr—C5'—C6'—C1'	−55.7 (2)
C6'—Cr—C2'—C1'	−29.77 (14)	C4'—C5'—C6'—Cr	55.4 (2)
C3'—Cr—C2'—C1'	−131.5 (2)	C2'—C1'—C6'—C5'	2.8 (4)
C5'—Cr—C2'—C1'	−66.47 (15)	C3—C1'—C6'—C5'	−179.4 (2)
C4'—Cr—C2'—C1'	−102.44 (16)	Cr—C1'—C6'—C5'	56.1 (2)
C1'—C2'—C3'—C4'	1.5 (4)	C2'—C1'—C6'—Cr	−53.3 (2)
Cr—C2'—C3'—C4'	−55.2 (2)	C3—C1'—C6'—Cr	124.6 (2)
C1'—C2'—C3'—Cr	56.7 (2)	C11—Cr—C6'—C5'	−167.85 (15)
C11—Cr—C3'—C2'	60.24 (18)	C12—Cr—C6'—C5'	19.0 (2)
C12—Cr—C3'—C2'	151.31 (17)	C13—Cr—C6'—C5'	105.92 (16)
C13—Cr—C3'—C2'	−100.7 (4)	C2'—Cr—C6'—C5'	−102.57 (16)
C6'—Cr—C3'—C2'	−66.83 (16)	C1'—Cr—C6'—C5'	−132.7 (2)
C1'—Cr—C3'—C2'	−29.73 (15)	C3'—Cr—C6'—C5'	−65.54 (15)
C5'—Cr—C3'—C2'	−103.53 (17)	C4'—Cr—C6'—C5'	−29.31 (14)
C4'—Cr—C3'—C2'	−131.7 (2)	C11—Cr—C6'—C1'	−35.1 (2)
C11—Cr—C3'—C4'	−168.06 (16)	C12—Cr—C6'—C1'	151.72 (18)
C12—Cr—C3'—C4'	−76.99 (17)	C13—Cr—C6'—C1'	−121.35 (16)
C13—Cr—C3'—C4'	31.0 (5)	C2'—Cr—C6'—C1'	30.16 (14)
C2'—Cr—C3'—C4'	131.7 (2)	C3'—Cr—C6'—C1'	67.20 (15)
C6'—Cr—C3'—C4'	64.87 (16)	C5'—Cr—C6'—C1'	132.7 (2)
C1'—Cr—C3'—C4'	101.97 (17)	C4'—Cr—C6'—C1'	103.42 (16)
C5'—Cr—C3'—C4'	28.17 (15)	C5—C6—C7—O7	−177.2 (3)
O5—C2—C3—C4	−2.0 (4)	C5—C6—C7—C8	3.3 (4)
O5—C2—C3—C1'	179.2 (2)	O7—C7—C8—C9	179.0 (3)
C6'—C1'—C3—C2	142.3 (3)	C6—C7—C8—C9	−1.6 (4)
C2'—C1'—C3—C2	−39.9 (4)	C7—C8—C9—O5	179.3 (2)
Cr—C1'—C3—C2	−127.5 (2)	C7—C8—C9—C10	−1.8 (4)
C6'—C1'—C3—C4	−36.6 (3)	O5—C9—C10—C5	−177.9 (2)
C2'—C1'—C3—C4	141.3 (2)	C8—C9—C10—C5	3.3 (4)
Cr—C1'—C3—C4	53.6 (3)	O5—C9—C10—C4	4.3 (4)
C2—C3—C4—O4	−172.4 (3)	C8—C9—C10—C4	−174.6 (2)
C1'—C3—C4—O4	6.4 (4)	C6—C5—C10—C9	−1.5 (4)
C2—C3—C4—C10	7.1 (4)	C6—C5—C10—C4	176.3 (3)
C1'—C3—C4—C10	−174.1 (2)	O4—C4—C10—C9	171.3 (3)
C2'—C3'—C4'—O4'	179.6 (2)	C3—C4—C10—C9	−8.3 (4)
Cr—C3'—C4'—O4'	125.8 (2)	O4—C4—C10—C5	−6.5 (4)
C2'—C3'—C4'—C5'	1.1 (4)	C3—C4—C10—C5	174.0 (2)
Cr—C3'—C4'—C5'	−52.7 (2)	C5'—C4'—O4'—C41'	15.9 (4)
C2'—C3'—C4'—Cr	53.8 (2)	C3'—C4'—O4'—C41'	−162.6 (2)
C11—Cr—C4'—O4'	−88.0 (3)	Cr—C4'—O4'—C41'	−77.7 (3)
C12—Cr—C4'—O4'	−3.0 (2)	C3—C2—O5—C9	−2.6 (4)
C13—Cr—C4'—O4'	83.4 (3)	C10—C9—O5—C2	1.4 (4)
C2'—Cr—C4'—O4'	−136.3 (3)	C8—C9—O5—C2	−179.7 (2)
C6'—Cr—C4'—O4'	149.5 (3)	C8—C7—O7—C71	−5.5 (4)
C1'—Cr—C4'—O4'	−173.8 (2)	C6—C7—O7—C71	175.0 (3)
C3'—Cr—C4'—O4'	−106.9 (3)

Experimental details

Crystal data
Chemical formula	[Cr(C₁₇H₁₄O₄)(CO)₃]
M_r	418.31
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	12.3454 (7), 17.9984 (8), 7.9988 (4)
β (°)	103.733 (2)
V (Å³)	1726.50 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.71
Crystal size (mm)	0.43 × 0.23 × 0.1

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.751, 0.933
No. of measured, independent and observed [I > 2σ(I)] reflections	9320, 4145, 3393
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.117, 1.08
No. of reflections	4145
No. of parameters	255
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.86, −0.41

Computer programs: APEX2 (Bruker, 2005), SAINT-Plus (Bruker, 2004), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2005), WinGX (Farrugia, 1999).

Acknowledgements

Financial assistance from the University of the Free State and SASOL to JHvT is gratefully acknowledged. We would like to express our gratitude to the School of Chemistry at the University of the Witwatersrand for the use of the diffractometer. Special thanks are due to Dr M. A. Fernandes. Opinions, findings, conclusions or recommendations expressed in this material are those of the authors and do not necessarily reflect the views of SASOL.

References

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