Racemic tricarbon-yl[7-meth-oxy-2-(η-phen-yl)chromane]-chromium(0).

In the title compound, [Cr(C(16)H(16)O(2))(CO)(3)], the Cr(0) atom of the Cr(CO)(3) unit is coordinated to the phenyl ring of the flavan ligand in an η(6) mode, with a normal arene-to-metal distance. The Cr(CO)(3) unit exhibits a three-legged piano-stool conformation, while the dihydro-pyran ring displays a distorted envelope configuration. The phenyl ring is twisted away from the fused ring system by 25.5 (2)°. The meth-oxy group is almost coplanar with the phenyl ring [C(Me)-O-C(ar)-C(ar) torsion angle = 8.46 (2)°]. The crystal packing is stabilized by inter-molecular C-H⋯O inter-actions.

Related literature

For similar structures, see: van Tonder et al. (2010a ▶,b ▶) and for other related structures, see: van Tonder et al. (2009a ▶,b ▶). For the synthesis of the title compound, see: Müller et al. (1999 ▶) and for the sythesis of 7-meth­oxy­flavan-4-one, see: Sato et al. (2006 ▶). For standard bond lengths, see: Allen et al. (1987 ▶). For the importance of flavonoids in biological investigations, see: Rice-Evans & Packer (2003 ▶). For the use of tricarbon­yl(arene)chromium complexes in regioselective organic synthesis, see: Muschalek et al. (2007 ▶).

Experimental

Crystal data

[Cr(C16H16O2)(CO)3]

M = 376.32

Monoclinic,

a = 9.7703 (5) Å

b = 19.1820 (9) Å

c = 8.8049 (4) Å

β = 97.494 (2)°

V = 1636.07 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.73 mm−1

T = 100 K

0.34 × 0.23 × 0.08 mm

Data collection

Bruker X8 APEXII 4K KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.818, T max = 0.942

29057 measured reflections

4069 independent reflections

3526 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.090

S = 1.00

4069 reflections

222 parameters

H-atom parameters constrained

Δρmax = 0.73 e Å−3

Δρmin = −0.52 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT-Plus (Bruker, 2008 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenberg & Putz, 2005 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811008683/hp2002sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811008683/hp2002Isup2.hkl

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

[Cr(C16H16O2)(CO)3]	F(000) = 776
Mr = 376.32	Dx = 1.528 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.7703 (5) Å	Cell parameters from 9920 reflections
b = 19.1820 (9) Å	θ = 3.0–28.2°
c = 8.8049 (4) Å	µ = 0.73 mm−1
β = 97.494 (2)°	T = 100 K
V = 1636.07 (14) Å3	Plate, yellow
Z = 4	0.34 × 0.23 × 0.08 mm

Bruker X8 APEXII 4K KappaCCD diffractometer	4069 independent reflections
graphite	3526 reflections with I > 2σ(I)
Detector resolution: 8.5 pixels mm-1	Rint = 0.033
φ and ω scans	θmax = 28.3°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −13→9
Tmin = 0.818, Tmax = 0.942	k = −25→25
29057 measured reflections	l = −11→11

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0434P)2 + 1.6967P] where P = (Fo2 + 2Fc2)/3
4069 reflections	(Δ/σ)max = 0.015
222 parameters	Δρmax = 0.73 e Å−3
0 restraints	Δρmin = −0.52 e Å−3

Experimental. The intensity data was collected on a Bruker X8 ApexII 4 K Kappa CCD diffractometer using an exposure time of 15 s/frame. A total of 1821 frames were collected with a frame width of 0.5° covering up to θ = 28.18° with 99.7% completeness accomplished.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
C1	0.3380 (2)	0.29331 (9)	0.6478 (2)	0.0208 (4)
H1A	0.291	0.2854	0.7355	0.031*
H1B	0.3066	0.3363	0.5995	0.031*
H1C	0.4356	0.2959	0.6798	0.031*
C1'	0.17467 (19)	−0.11113 (9)	0.36846 (19)	0.0178 (3)
C2	0.28858 (19)	−0.07158 (9)	0.4658 (2)	0.0190 (3)
H2	0.3777	−0.0837	0.4332	0.023*
C2'	0.19981 (19)	−0.17979 (9)	0.3254 (2)	0.0196 (3)
H2'	0.2859	−0.1997	0.355	0.023*
C3'	0.0952 (2)	−0.21918 (9)	0.2369 (2)	0.0213 (4)
H3'	0.1123	−0.265	0.2106	0.026*
C3	0.29216 (19)	−0.08786 (9)	0.6350 (2)	0.0202 (4)
H3A	0.3106	−0.1371	0.6528	0.024*
H3B	0.2034	−0.0771	0.6676	0.024*
C4'	−0.03356 (19)	−0.18914 (10)	0.1893 (2)	0.0219 (4)
H4'	−0.1018	−0.2147	0.1301	0.026*
C4	0.40480 (18)	−0.04451 (8)	0.72666 (19)	0.0167 (3)
H4A	0.4003	−0.0501	0.8354	0.02*
H4B	0.4948	−0.0602	0.7056	0.02*
C5	0.43124 (17)	0.08604 (9)	0.77979 (19)	0.0159 (3)
H5	0.4782	0.0757	0.8759	0.019*
C5'	−0.05972 (19)	−0.11962 (10)	0.2316 (2)	0.0220 (4)
H5'	−0.1454	−0.0995	0.2003	0.026*
C6	0.41013 (17)	0.15570 (9)	0.73907 (19)	0.0159 (3)
H6	0.4428	0.1912	0.8062	0.019*
C6'	0.04282 (19)	−0.08107 (9)	0.3203 (2)	0.0197 (3)
H6'	0.0248	−0.0355	0.348	0.024*
C7	0.33885 (17)	0.17112 (9)	0.59536 (19)	0.0159 (3)
C7'	0.20844 (19)	−0.03456 (9)	0.0866 (2)	0.0210 (2)
C8	0.29047 (18)	0.11775 (9)	0.49617 (19)	0.0176 (3)
H8	0.2422	0.1281	0.4007	0.021*
C8'	0.26596 (17)	−0.16022 (8)	0.02184 (19)	0.0168 (3)
C9	0.31439 (18)	0.04906 (9)	0.53999 (19)	0.0163 (3)
C9'	0.02989 (18)	−0.11148 (9)	−0.0765 (2)	0.0185 (3)
C10	0.38501 (17)	0.03117 (8)	0.68272 (19)	0.0148 (3)
O1	0.25988 (15)	0.00078 (6)	0.43410 (14)	0.0232 (3)
O2	0.30939 (14)	0.23734 (6)	0.54184 (14)	0.0210 (3)
O3	0.26044 (13)	0.01758 (6)	0.06402 (15)	0.0210 (2)
O4	0.35317 (13)	−0.18513 (7)	−0.03763 (15)	0.0218 (3)
O5	−0.02741 (14)	−0.10672 (8)	−0.19953 (15)	0.0280 (3)
Cr1	0.12859 (3)	−0.120499 (13)	0.11540 (3)	0.01295 (8)

	U11	U22	U33	U12	U13	U23
C1	0.0271 (9)	0.0133 (8)	0.0223 (9)	−0.0016 (6)	0.0046 (7)	−0.0035 (6)
C1'	0.0238 (9)	0.0148 (8)	0.0143 (8)	−0.0025 (6)	0.0010 (6)	0.0018 (6)
C2	0.0226 (8)	0.0155 (8)	0.0185 (8)	−0.0028 (6)	0.0008 (7)	0.0002 (6)
C2'	0.0249 (9)	0.0141 (8)	0.0184 (8)	−0.0011 (6)	−0.0022 (7)	0.0037 (6)
C3'	0.0295 (10)	0.0125 (7)	0.0214 (9)	−0.0055 (7)	0.0017 (7)	0.0026 (6)
C3	0.0240 (9)	0.0170 (8)	0.0189 (8)	−0.0025 (7)	0.0007 (7)	0.0026 (6)
C4'	0.0204 (9)	0.0238 (9)	0.0215 (8)	−0.0092 (7)	0.0030 (7)	0.0029 (7)
C4	0.0190 (8)	0.0152 (8)	0.0149 (7)	0.0005 (6)	−0.0017 (6)	0.0014 (6)
C5	0.0134 (7)	0.0194 (8)	0.0145 (7)	−0.0003 (6)	−0.0003 (6)	0.0010 (6)
C5'	0.0157 (8)	0.0282 (9)	0.0231 (9)	−0.0005 (7)	0.0062 (7)	0.0040 (7)
C6	0.0146 (8)	0.0168 (8)	0.0160 (8)	−0.0024 (6)	0.0013 (6)	−0.0034 (6)
C6'	0.0243 (9)	0.0188 (8)	0.0170 (8)	0.0011 (7)	0.0072 (7)	−0.0003 (6)
C7	0.0168 (8)	0.0143 (7)	0.0169 (8)	0.0001 (6)	0.0029 (6)	0.0005 (6)
C7'	0.0240 (5)	0.0159 (4)	0.0236 (5)	−0.0015 (4)	0.0056 (4)	0.0004 (4)
C8	0.0218 (8)	0.0169 (8)	0.0130 (7)	−0.0012 (6)	−0.0016 (6)	0.0016 (6)
C8'	0.0179 (8)	0.0128 (7)	0.0184 (8)	−0.0028 (6)	−0.0019 (6)	−0.0013 (6)
C9	0.0215 (8)	0.0140 (7)	0.0134 (7)	−0.0029 (6)	0.0019 (6)	−0.0017 (6)
C9'	0.0143 (8)	0.0202 (8)	0.0213 (8)	0.0005 (6)	0.0036 (6)	−0.0005 (6)
C10	0.0134 (7)	0.0159 (7)	0.0151 (7)	0.0004 (6)	0.0025 (6)	0.0016 (6)
O1	0.0419 (8)	0.0117 (6)	0.0135 (6)	−0.0046 (5)	−0.0057 (5)	0.0009 (4)
O2	0.0314 (7)	0.0122 (6)	0.0177 (6)	0.0000 (5)	−0.0027 (5)	0.0002 (5)
O3	0.0240 (5)	0.0159 (4)	0.0236 (5)	−0.0015 (4)	0.0056 (4)	0.0004 (4)
O4	0.0190 (6)	0.0206 (6)	0.0258 (7)	0.0003 (5)	0.0032 (5)	−0.0063 (5)
O5	0.0236 (7)	0.0394 (8)	0.0195 (7)	0.0032 (6)	−0.0032 (5)	0.0001 (6)
Cr1	0.01308 (14)	0.01116 (13)	0.01423 (14)	−0.00064 (9)	0.00033 (9)	−0.00028 (9)

C1—O2	1.426 (2)	C4—H4A	0.97
C1—H1A	0.96	C4—H4B	0.97
C1—H1B	0.96	C5—C6	1.392 (2)
C1—H1C	0.96	C5—C10	1.393 (2)
C1'—C2'	1.401 (2)	C5—H5	0.93
C1'—C6'	1.424 (3)	C5'—C6'	1.399 (3)
C1'—C2	1.517 (2)	C5'—Cr1	2.2187 (18)
C1'—Cr1	2.2221 (17)	C5'—H5'	0.93
C2—O1	1.436 (2)	C6—C7	1.394 (2)
C2—C3	1.518 (2)	C6—H6	0.93
C2—H2	0.98	C6'—Cr1	2.2188 (17)
C2'—C3'	1.419 (2)	C6'—H6'	0.93
C2'—Cr1	2.2044 (17)	C7—O2	1.372 (2)
C2'—H2'	0.93	C7—C8	1.388 (2)
C3'—C4'	1.397 (3)	C7'—O3	1.151 (2)
C3'—Cr1	2.2194 (17)	C7'—Cr1	1.8552 (18)
C3'—H3'	0.93	C8—C9	1.384 (2)
C3—C4	1.524 (2)	C8—H8	0.93
C3—H3A	0.97	C8'—O4	1.160 (2)
C3—H3B	0.97	C8'—Cr1	1.8300 (18)
C4'—C5'	1.417 (3)	C9—O1	1.3716 (19)
C4'—Cr1	2.2216 (17)	C9—C10	1.395 (2)
C4'—H4'	0.93	C9'—O5	1.156 (2)
C4—C10	1.508 (2)	C9'—Cr1	1.8413 (18)
O2—C1—H1A	109.5	C5'—C6'—C1'	120.42 (16)
O2—C1—H1B	109.5	C5'—C6'—Cr1	71.62 (10)
H1A—C1—H1B	109.5	C1'—C6'—Cr1	71.42 (10)
O2—C1—H1C	109.5	C5'—C6'—H6'	119.8
H1A—C1—H1C	109.5	C1'—C6'—H6'	119.8
H1B—C1—H1C	109.5	Cr1—C6'—H6'	129.6
C2'—C1'—C6'	118.91 (16)	O2—C7—C8	115.32 (14)
C2'—C1'—C2	118.79 (16)	O2—C7—C6	124.44 (15)
C6'—C1'—C2	122.29 (15)	C8—C7—C6	120.24 (15)
C2'—C1'—Cr1	70.86 (10)	O3—C7'—Cr1	177.22 (16)
C6'—C1'—Cr1	71.16 (10)	C9—C8—C7	119.69 (15)
C2—C1'—Cr1	130.16 (12)	C9—C8—H8	120.2
O1—C2—C1'	105.27 (14)	C7—C8—H8	120.2
O1—C2—C3	111.62 (14)	O4—C8'—Cr1	179.72 (16)
C1'—C2—C3	111.90 (14)	O1—C9—C8	114.63 (14)
O1—C2—H2	109.3	O1—C9—C10	123.27 (15)
C1'—C2—H2	109.3	C8—C9—C10	122.07 (15)
C3—C2—H2	109.3	O5—C9'—Cr1	177.22 (16)
C1'—C2'—C3'	120.66 (17)	C5—C10—C9	116.69 (15)
C1'—C2'—Cr1	72.24 (10)	C5—C10—C4	123.31 (15)
C3'—C2'—Cr1	71.86 (10)	C9—C10—C4	119.97 (15)
C1'—C2'—H2'	119.7	C9—O1—C2	118.15 (13)
C3'—C2'—H2'	119.7	C7—O2—C1	117.25 (13)
Cr1—C2'—H2'	128.5	C8'—Cr1—C9'	87.31 (8)
C4'—C3'—C2'	120.04 (17)	C8'—Cr1—C7'	87.84 (8)
C4'—C3'—Cr1	71.75 (10)	C9'—Cr1—C7'	88.31 (8)
C2'—C3'—Cr1	70.71 (10)	C8'—Cr1—C2'	89.59 (7)
C4'—C3'—H3'	120	C9'—Cr1—C2'	152.67 (7)
C2'—C3'—H3'	120	C7'—Cr1—C2'	118.72 (7)
Cr1—C3'—H3'	130.1	C8'—Cr1—C5'	155.74 (7)
C2—C3—C4	109.27 (14)	C9'—Cr1—C5'	93.20 (7)
C2—C3—H3A	109.8	C7'—Cr1—C5'	116.42 (8)
C4—C3—H3A	109.8	C2'—Cr1—C5'	78.89 (7)
C2—C3—H3B	109.8	C8'—Cr1—C6'	152.24 (7)
C4—C3—H3B	109.8	C9'—Cr1—C6'	120.40 (7)
H3A—C3—H3B	108.3	C7'—Cr1—C6'	91.05 (7)
C3'—C4'—C5'	119.71 (16)	C2'—Cr1—C6'	66.76 (7)
C3'—C4'—Cr1	71.57 (10)	C5'—Cr1—C6'	36.75 (7)
C5'—C4'—Cr1	71.28 (10)	C8'—Cr1—C3'	91.40 (7)
C3'—C4'—H4'	120.1	C9'—Cr1—C3'	115.48 (7)
C5'—C4'—H4'	120.1	C7'—Cr1—C3'	156.15 (8)
Cr1—C4'—H4'	129.4	C2'—Cr1—C3'	37.43 (6)
C10—C4—C3	109.26 (13)	C5'—Cr1—C3'	66.50 (7)
C10—C4—H4A	109.8	C6'—Cr1—C3'	78.69 (7)
C3—C4—H4A	109.8	C8'—Cr1—C1'	114.87 (7)
C10—C4—H4B	109.8	C9'—Cr1—C1'	157.81 (7)
C3—C4—H4B	109.8	C7'—Cr1—C1'	91.79 (7)
H4A—C4—H4B	108.3	C2'—Cr1—C1'	36.90 (6)
C6—C5—C10	122.81 (15)	C5'—Cr1—C1'	66.97 (7)
C6—C5—H5	118.6	C6'—Cr1—C1'	37.42 (7)
C10—C5—H5	118.6	C3'—Cr1—C1'	66.98 (6)
C6'—C5'—C4'	120.25 (17)	C8'—Cr1—C4'	118.55 (7)
C6'—C5'—Cr1	71.63 (10)	C9'—Cr1—C4'	90.93 (7)
C4'—C5'—Cr1	71.51 (10)	C7'—Cr1—C4'	153.54 (8)
C6'—C5'—H5'	119.9	C2'—Cr1—C4'	66.91 (7)
C4'—C5'—H5'	119.9	C5'—Cr1—C4'	37.21 (7)
Cr1—C5'—H5'	129.4	C6'—Cr1—C4'	66.71 (7)
C5—C6—C7	118.50 (15)	C3'—Cr1—C4'	36.68 (7)
C5—C6—H6	120.8	C1'—Cr1—C4'	79.24 (7)
C7—C6—H6	120.8

D—H···A	D—H	H···A	D···A	D—H···A
C4'—H4'···O2i	0.93	2.54	3.459 (2)	169
C2'—H2'···O4ii	0.93	2.46	3.153 (2)	132
C1—H1C···O4iii	0.96	2.57	3.314 (2)	134

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4′—H4′⋯O2i	0.93	2.54	3.459 (2)	169
C2′—H2′⋯O4ii	0.93	2.46	3.153 (2)	132
C1—H1C⋯O4iii	0.96	2.57	3.314 (2)	134

Symmetry codes: (i) ; (ii) ; (iii) .