Racemic tricarbonyl[(4a,5,6,7,8,8a-η)-2-phenyl-3,4-dihydro-2H-1-benzopyran]chromium(0).

The title compound, [Cr(C(15)H(14)O)(CO)(3)], displays a distorted envelope configuration of the dihydro-pyrane ring. The dihedral angle between the phenyl and phenyl-ene rings is 50.63 (4)°. The Cr(0) atom is coordinated by three CO groups and the phenyl-ene ring of the flavan ligand in an η(6) mode, with a common arene-to-metal distance.

Related literature

For general background to chromium(0) complexes of the type [Cr(flav)(CO)3] (flav = flavan, flavone or isoflavone ligand), see: Muschalek et al. (2007 ▶). For related structures, see: van Tonder et al. (2009a ▶,b ▶). For the synthesis, see: Müller et al. (1999 ▶).

Experimental

Crystal data

[Cr(C15H14O)(CO)3]

M = 346.29

Monoclinic,

a = 12.0275 (2) Å

b = 13.1454 (2) Å

c = 10.4473 (2) Å

β = 111.717 (1)°

V = 1534.55 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.76 mm−1

T = 173 K

0.46 × 0.34 × 0.11 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.766, T max = 0.938

20468 measured reflections

5342 independent reflections

3728 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.097

S = 0.95

5342 reflections

208 parameters

H-atom parameters constrained

Δρmax = 0.67 e Å−3

Δρmin = −0.32 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT-Plus (Bruker, 2007 ▶); 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, 1999 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810031028/hy2329sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810031028/hy2329Isup2.hkl

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

[Cr(C15H14O)(CO)3]	F(000) = 712
Mr = 346.29	Dx = 1.499 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 4557 reflections
a = 12.0275 (2) Å	θ = 2.4–30.0°
b = 13.1454 (2) Å	µ = 0.76 mm−1
c = 10.4473 (2) Å	T = 173 K
β = 111.717 (1)°	Plate, yellow
V = 1534.55 (5) Å3	0.46 × 0.34 × 0.11 mm
Z = 4

Bruker APEXII CCD diffractometer	3728 reflections with I > 2σ(I)
graphite	Rint = 0.050
φ and ω scans	θmax = 32.1°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −17→14
Tmin = 0.766, Tmax = 0.938	k = −19→19
20468 measured reflections	l = −14→15
5342 independent reflections

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097	H-atom parameters constrained
S = 0.95	w = 1/[σ2(Fo2) + (0.0469P)2] where P = (Fo2 + 2Fc2)/3
5342 reflections	(Δ/σ)max = 0.001
208 parameters	Δρmax = 0.67 e Å−3
0 restraints	Δρmin = −0.32 e Å−3

Experimental. The intensity data was collected on a Bruker APEXII CCD diffractometer using a frame width of 0.5° covering up to θ = 32.06° with 99.8% completeness accomplished.Spectroscopic data for the flavan ligand: 1H NMR (CDCl3, 600 MHz) δ p.p.m. 7.46 – 7.30 (5H, m, Ar—H), 7.21 – 7.10 (2H, m, Ar—H), 6.94 – 6.86 (2H, m, Ar—H), 5.08 (1H, dd, J = 2.45, 9.98 Hz), 3.02 (1H, ddd, J = 6.03, 11.02, 16.46 Hz), 2.81 (1H, ddd, J = 3.58, 4.71, 16.46 Hz), 2.27 – 2.04 (2H, m);13C NMR (600 MHz, CDCl3) δ p.p.m. 25.18, 30.06, 77.82, 117.04, 120.43, 121.93, 126.10, 127.45, 127.91, 128.61, 129.63, 141.87, 155.25.Spectroscopic data for the title compound, tricarbonyl(A-η6flavan)chromium(0): Note: A, B and C-ring labelling refers to the benzene, phenyl and dihydropyrane rings respectively. 1H NMR (600 MHz, CDCl3) δ p.p.m. 7.46 (2H, d, J = 7.30 Hz), 7.40 (2H, dd, J = 7.24, 7.30 Hz), 7.37 – 7.35 (1H, m), 5.56 (1H, d, J = 6.03 Hz), 5.48 (1H, dd, J = 6.02, 6.69 Hz), 5.20 (1H, d, J = 6.69 Hz), 4.90 – 4.88 (2H, m), 3.00 (1H, ddd, J = 5.27, 12.42, 15.95 Hz), 2.64 (1H, dd, J = 4.14, 15.95 Hz), 2.31 (1H, ddd, J = 4.14, 12.42, 13.93 Hz), 2.17 (1H, dd, J = 5.27, 13.93 Hz);13C NMR (600 MHz, CDCl3) δ p.p.m. 25.94 (C-4), 29.67 (C-3), 80.00 (C-2/6/8), 80.29 (C-2/6/8), 85.87 (C-2/6/8), 94.50 (C-5/7), 95.60 (C-5/7), 126.49 (C-2' and C-6'), 128.80, 128.89, 139.71, 234.06 (–Cr(CO)3);MS m/z 346 (M+, 39.0), 290 (2.7), 263 (22.1), 222 (56.9), 193 (12.0), 167 (100.0), 158 (99.8), 149 (68.9),129 (1.9), 127 (13.0), 121 (27.0), 106 (31.3), 104 (4.8), 103 (7.8).

	x	y	z	Uiso*/Ueq
C1'	0.42382 (14)	0.18308 (12)	0.19968 (17)	0.0245 (3)
C2	0.50936 (14)	0.20966 (13)	0.12917 (17)	0.0263 (3)
H2	0.4643	0.2420	0.0405	0.032*
C2'	0.32347 (17)	0.24327 (15)	0.1760 (2)	0.0372 (4)
H2'	0.3095	0.2986	0.1167	0.045*
C3	0.60863 (15)	0.27990 (13)	0.21249 (18)	0.0293 (4)
H3A	0.6526	0.2491	0.3013	0.035*
H3B	0.5746	0.3433	0.2285	0.035*
C3'	0.24388 (17)	0.22168 (16)	0.2401 (2)	0.0405 (5)
H3'	0.1772	0.2629	0.2240	0.049*
C4	0.69396 (15)	0.30169 (12)	0.13848 (18)	0.0269 (3)
H4A	0.6552	0.3457	0.0600	0.032*
H4B	0.7645	0.3364	0.2005	0.032*
C4'	0.26295 (15)	0.13974 (15)	0.32735 (18)	0.0327 (4)
H4'	0.2084	0.1245	0.3686	0.039*
C5'	0.36356 (16)	0.08021 (13)	0.35341 (18)	0.0295 (4)
H5'	0.3773	0.0254	0.4135	0.035*
C5	0.83325 (14)	0.19620 (13)	0.05541 (16)	0.0261 (3)
H5	0.8817	0.2531	0.0654	0.031*
C6'	0.44412 (14)	0.10155 (12)	0.29068 (18)	0.0260 (3)
H6'	0.5119	0.0614	0.3094	0.031*
C6	0.86366 (15)	0.10536 (13)	0.00632 (17)	0.0290 (4)
H6	0.9293	0.1028	−0.0204	0.035*
C7	0.79393 (15)	0.01836 (14)	−0.00212 (18)	0.0309 (4)
H7	0.8147	−0.0427	−0.0322	0.037*
C8	0.69312 (14)	0.02274 (13)	0.03445 (17)	0.0278 (4)
H8	0.6488	−0.0357	0.0319	0.033*
C9	0.65942 (13)	0.11637 (12)	0.07510 (16)	0.0223 (3)
C10	0.72998 (13)	0.20345 (12)	0.09035 (15)	0.0219 (3)
C11	0.79274 (15)	0.03598 (13)	0.34020 (18)	0.0297 (4)
C12	0.96333 (16)	−0.02379 (14)	0.26452 (19)	0.0334 (4)
C13	0.95879 (14)	0.16059 (13)	0.34028 (17)	0.0267 (3)
O1	0.75227 (13)	0.00961 (11)	0.41970 (15)	0.0468 (4)
O2	1.03289 (14)	−0.08866 (11)	0.29813 (18)	0.0576 (4)
O3	1.02610 (11)	0.21213 (11)	0.42255 (14)	0.0422 (3)
O5	0.55780 (9)	0.11377 (8)	0.10382 (12)	0.0260 (2)
Cr	0.85184 (2)	0.078021 (19)	0.21024 (3)	0.02026 (7)

	U11	U22	U33	U12	U13	U23
C1'	0.0243 (7)	0.0262 (8)	0.0257 (8)	−0.0011 (6)	0.0126 (6)	−0.0017 (6)
C2	0.0242 (8)	0.0296 (8)	0.0261 (8)	0.0011 (6)	0.0106 (6)	0.0006 (7)
C2'	0.0396 (10)	0.0401 (10)	0.0380 (10)	0.0150 (8)	0.0215 (8)	0.0135 (8)
C3	0.0306 (9)	0.0270 (8)	0.0338 (9)	−0.0040 (6)	0.0160 (7)	−0.0058 (7)
C3'	0.0318 (9)	0.0562 (12)	0.0377 (10)	0.0187 (9)	0.0179 (8)	0.0066 (9)
C4	0.0286 (8)	0.0225 (7)	0.0312 (9)	−0.0040 (6)	0.0131 (7)	0.0017 (7)
C4'	0.0264 (8)	0.0472 (11)	0.0288 (9)	−0.0049 (7)	0.0152 (7)	−0.0042 (8)
C5'	0.0336 (9)	0.0287 (8)	0.0288 (9)	−0.0049 (7)	0.0147 (7)	0.0016 (7)
C5	0.0237 (8)	0.0346 (9)	0.0218 (8)	−0.0047 (6)	0.0105 (6)	0.0040 (7)
C6'	0.0226 (8)	0.0257 (8)	0.0296 (9)	0.0014 (6)	0.0094 (6)	−0.0017 (7)
C6	0.0251 (8)	0.0436 (10)	0.0229 (8)	−0.0020 (7)	0.0140 (6)	−0.0025 (7)
C7	0.0283 (8)	0.0389 (10)	0.0277 (9)	−0.0027 (7)	0.0131 (7)	−0.0133 (8)
C8	0.0247 (8)	0.0316 (9)	0.0283 (8)	−0.0079 (6)	0.0112 (7)	−0.0119 (7)
C9	0.0182 (7)	0.0304 (8)	0.0189 (7)	−0.0032 (6)	0.0075 (6)	−0.0037 (6)
C10	0.0212 (7)	0.0267 (8)	0.0181 (7)	−0.0016 (6)	0.0076 (6)	0.0020 (6)
C11	0.0268 (8)	0.0330 (9)	0.0288 (9)	0.0007 (7)	0.0096 (7)	0.0045 (7)
C12	0.0334 (9)	0.0314 (9)	0.0372 (10)	0.0039 (7)	0.0150 (8)	−0.0010 (8)
C13	0.0208 (7)	0.0347 (9)	0.0263 (8)	0.0028 (6)	0.0106 (6)	−0.0032 (7)
O1	0.0496 (9)	0.0583 (9)	0.0418 (8)	0.0003 (7)	0.0278 (7)	0.0146 (7)
O2	0.0532 (10)	0.0460 (9)	0.0714 (12)	0.0253 (7)	0.0206 (9)	0.0070 (8)
O3	0.0290 (7)	0.0562 (8)	0.0387 (7)	−0.0062 (6)	0.0091 (6)	−0.0196 (7)
O5	0.0200 (5)	0.0275 (6)	0.0347 (6)	−0.0051 (4)	0.0149 (5)	−0.0083 (5)
Cr	0.01890 (12)	0.02262 (13)	0.02079 (13)	−0.00077 (9)	0.00912 (9)	−0.00132 (10)

C1'—C2'	1.387 (2)	C5—H5	0.9300
C1'—C6'	1.393 (2)	C6'—H6'	0.9300
C1'—C2	1.511 (2)	C6—C7	1.401 (2)
C2—O5	1.4535 (19)	C6—H6	0.9300
C2—C3	1.506 (2)	C7—C8	1.401 (2)
C2—H2	0.9800	C7—H7	0.9300
C2'—C3'	1.385 (3)	C8—C9	1.410 (2)
C2'—H2'	0.9300	C8—H8	0.9300
C3—C4	1.523 (2)	C9—O5	1.3627 (18)
C3—H3A	0.9700	C9—C10	1.399 (2)
C3—H3B	0.9700	C11—O1	1.160 (2)
C3'—C4'	1.374 (3)	C12—O2	1.155 (2)
C3'—H3'	0.9300	C13—O3	1.157 (2)
C4—C10	1.506 (2)	C5—Cr	2.1936 (18)
C4—H4A	0.9700	C6—Cr	2.2163 (19)
C4—H4B	0.9700	C7—Cr	2.2087 (19)
C4'—C5'	1.381 (2)	C8—Cr	2.2251 (17)
C4'—H4'	0.9300	C9—Cr	2.2773 (17)
C5'—C6'	1.384 (2)	C10—Cr	2.2532 (17)
C5'—H5'	0.9300	C11—Cr	1.8353 (19)
C5—C6	1.401 (2)	C12—Cr	1.8298 (19)
C5—C10	1.421 (2)	C13—Cr	1.8399 (17)
C2'—C1'—C6'	118.79 (15)	C9—C8—Cr	73.78 (9)
C2'—C1'—C2	119.07 (15)	C7—C8—H8	120.2
C6'—C1'—C2	122.11 (14)	C9—C8—H8	120.2
O5—C2—C3	110.59 (13)	Cr—C8—H8	127.0
O5—C2—C1'	106.22 (13)	O5—C9—C10	123.47 (14)
C3—C2—C1'	113.41 (14)	O5—C9—C8	115.20 (14)
O5—C2—H2	108.8	C10—C9—C8	121.26 (14)
C3—C2—H2	108.8	O5—C9—Cr	130.29 (11)
C1'—C2—H2	108.8	C10—C9—Cr	71.08 (9)
C3'—C2'—C1'	120.57 (17)	C8—C9—Cr	69.75 (9)
C3'—C2'—H2'	119.7	C9—C10—C5	117.84 (15)
C1'—C2'—H2'	119.7	C9—C10—C4	120.15 (13)
C2—C3—C4	111.16 (14)	C5—C10—C4	121.99 (14)
C2—C3—H3A	109.4	C9—C10—Cr	72.96 (9)
C4—C3—H3A	109.4	C5—C10—Cr	69.09 (9)
C2—C3—H3B	109.4	C4—C10—Cr	130.54 (11)
C4—C3—H3B	109.4	O1—C11—Cr	178.15 (15)
H3A—C3—H3B	108.0	O2—C12—Cr	179.38 (19)
C4'—C3'—C2'	120.36 (17)	O3—C13—Cr	179.64 (17)
C4'—C3'—H3'	119.8	C9—O5—C2	118.10 (12)
C2'—C3'—H3'	119.8	C12—Cr—C11	89.46 (8)
C10—C4—C3	109.83 (13)	C12—Cr—C13	88.32 (8)
C10—C4—H4A	109.7	C11—Cr—C13	89.30 (8)
C3—C4—H4A	109.7	C12—Cr—C5	127.56 (7)
C10—C4—H4B	109.7	C11—Cr—C5	142.85 (7)
C3—C4—H4B	109.7	C13—Cr—C5	88.82 (8)
H4A—C4—H4B	108.2	C12—Cr—C7	88.52 (8)
C3'—C4'—C5'	119.60 (16)	C11—Cr—C7	124.86 (8)
C3'—C4'—H4'	120.2	C13—Cr—C7	145.65 (7)
C5'—C4'—H4'	120.2	C5—Cr—C7	66.58 (7)
C4'—C5'—C6'	120.51 (16)	C12—Cr—C6	96.67 (8)
C4'—C5'—H5'	119.7	C11—Cr—C6	160.06 (7)
C6'—C5'—H5'	119.7	C13—Cr—C6	109.76 (7)
C6—C5—C10	121.51 (15)	C5—Cr—C6	37.03 (6)
C6—C5—Cr	72.37 (10)	C7—Cr—C6	36.93 (7)
C10—C5—Cr	73.65 (9)	C12—Cr—C8	108.88 (8)
C6—C5—H5	119.2	C11—Cr—C8	93.63 (8)
C10—C5—H5	119.2	C13—Cr—C8	162.56 (7)
Cr—C5—H5	126.7	C5—Cr—C8	78.49 (7)
C5'—C6'—C1'	120.15 (15)	C7—Cr—C8	36.83 (6)
C5'—C6'—H6'	119.9	C6—Cr—C8	66.43 (7)
C1'—C6'—H6'	119.9	C12—Cr—C10	163.51 (7)
C5—C6—C7	119.17 (15)	C11—Cr—C10	106.33 (7)
C5—C6—Cr	70.60 (9)	C13—Cr—C10	96.43 (7)
C7—C6—Cr	71.24 (9)	C5—Cr—C10	37.25 (6)
C5—C6—H6	120.4	C7—Cr—C10	78.64 (7)
C7—C6—H6	120.4	C6—Cr—C10	66.85 (6)
Cr—C6—H6	130.2	C8—Cr—C10	66.24 (6)
C8—C7—C6	120.50 (16)	C12—Cr—C9	144.51 (7)
C8—C7—Cr	72.22 (10)	C11—Cr—C9	86.69 (7)
C6—C7—Cr	71.83 (10)	C13—Cr—C9	126.85 (7)
C8—C7—H7	119.8	C5—Cr—C9	65.36 (6)
C6—C7—H7	119.8	C7—Cr—C9	65.51 (6)
Cr—C7—H7	128.5	C6—Cr—C9	77.30 (6)
C7—C8—C9	119.50 (15)	C8—Cr—C9	36.47 (6)
C7—C8—Cr	70.95 (10)	C10—Cr—C9	35.96 (5)

Table 1

Selected bond lengths (Å)

C5—Cr	2.1936 (18)
C6—Cr	2.2163 (19)
C7—Cr	2.2087 (19)
C8—Cr	2.2251 (17)
C9—Cr	2.2773 (17)
C10—Cr	2.2532 (17)
C11—Cr	1.8353 (19)
C12—Cr	1.8298 (19)
C13—Cr	1.8399 (17)