Racemic tricarbon-yl(η-7-meth-oxy-flavan)chromium(0).

IN THE TITLE COMPOUND [SYSTEMATIC NAME: tricarbonyl(η(6)-7-methoxy-2-phenyl-3,4-dihydro-2H-1-benzopyran)chromium(0)], [Cr(C(16)H(16)O(2))(CO)(3)], the Cr(CO)(3) unit is coordinated by the phenyl-ene ring of the flavan ligand, exhibiting a three-legged piano-stool conformation, with a point to plane distance of 1.750 (1) Å. The phenyl ring is twisted away from the fused ring system by 36.49 (5)° (r.m.s. deviation = 0.027 Å; fitted atoms are the C(6) ring and the attached fused-ring C and O atoms). The dihydro-pyran ring displays a distorted envelope configuration by displacement of the phenyl-bearing and the adjacent ring C atoms from the fused-ring system plane by 0.356 (2) and 0.402 (2) Å, respectively.

Related literature

7-Meth­oxy­flavan was synthesized via hydrogenation from 7-meth­oxy­flavanone, as described by Sato et al. (2006 ▶). For coordination of 7-meth­oxy­flavan to chromium, see: Müller et al. (1999 ▶). For the importance of flavonoids in biological investigations, see: Rice-Evans & Packer (2003 ▶). For Cr(CO)3 coordination to the phenyl­ene ring of a flavanone compound, see: Dominique et al. (1999 ▶). For comparison bond distances, see: Allen et al. (1987 ▶). For related structures, see: van Tonder et al. (2009a ▶,b ▶). 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 = 9.8422 (2) Å

b = 12.3850 (3) Å

c = 15.0146 (3) Å

β = 115.171 (1)°

V = 1656.42 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.72 mm−1

T = 173 K

0.41 × 0.34 × 0.24 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.757, T max = 0.847

12982 measured reflections

3985 independent reflections

3224 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.085

S = 1.07

3985 reflections

227 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.40 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus and XPREP (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 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810024992/zb2005sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810024992/zb2005Isup2.hkl

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

[Cr(C16H16O2)(CO)3]	F(000) = 776
Mr = 376.32	Dx = 1.509 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5285 reflections
a = 9.8422 (2) Å	θ = 2.2–28.3°
b = 12.3850 (3) Å	µ = 0.72 mm−1
c = 15.0146 (3) Å	T = 173 K
β = 115.171 (1)°	Prism, yellow
V = 1656.42 (6) Å3	0.41 × 0.34 × 0.24 mm
Z = 4

Bruker APEXII CCD diffractometer	3224 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.030
Absorption correction: multi-scan (Bruker, 2004)	θmax = 28°, θmin = 2.2°
Tmin = 0.757, Tmax = 0.847	h = −11→12
12982 measured reflections	k = −16→16
3985 independent reflections	l = −19→19

Refinement on F2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.030	w = 1/[σ2(Fo2) + (0.0444P)2 + 0.0884P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.085	(Δ/σ)max = 0.001
S = 1.07	Δρmax = 0.25 e Å−3
3985 reflections	Δρmin = −0.40 e Å−3
227 parameters

Experimental. The intensity data was collected on a Bruker Apex II CCD diffractometer using a frame width of 0.5° covering up to θ = 28° with 100 % completeness accomplished.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

	x	y	z	Uiso*/Ueq
C1'	1.01976 (18)	0.59116 (14)	0.84890 (12)	0.0260 (3)
C2'	0.9566 (2)	0.69062 (15)	0.85055 (13)	0.0325 (4)
H2'	0.8506	0.6988	0.8213	0.039*
C2	0.92726 (18)	0.49179 (14)	0.80339 (12)	0.0268 (4)
H2	0.9703	0.4553	0.7618	0.032*
C3'	1.0487 (2)	0.77884 (16)	0.89526 (14)	0.0385 (4)
H3'	1.0052	0.8471	0.8958	0.046*
C3	0.92236 (18)	0.41073 (13)	0.87814 (12)	0.0276 (4)
H3A	0.8755	0.4443	0.9181	0.033*
H3B	1.0257	0.3886	0.923	0.033*
C4	0.83175 (18)	0.31200 (14)	0.82448 (12)	0.0272 (4)
H4A	0.8908	0.2687	0.798	0.033*
H4B	0.8107	0.2663	0.8713	0.033*
C4'	1.2029 (2)	0.76723 (16)	0.93867 (13)	0.0380 (4)
H4'	1.2654	0.8272	0.9696	0.046*
C5'	1.2657 (2)	0.66846 (16)	0.93694 (13)	0.0360 (4)
H5'	1.3717	0.6603	0.967	0.043*
C5	0.56441 (18)	0.27492 (13)	0.69612 (12)	0.0260 (4)
H5	0.5723	0.2037	0.7214	0.031*
C6	0.43161 (18)	0.30503 (13)	0.61485 (12)	0.0263 (3)
H6	0.3532	0.2541	0.5842	0.032*
C6'	1.17553 (18)	0.58135 (15)	0.89185 (12)	0.0295 (4)
H6'	1.2201	0.5138	0.89	0.035*
C7	0.41667 (18)	0.41122 (13)	0.57975 (11)	0.0247 (3)
C8	0.53223 (18)	0.48677 (13)	0.62755 (12)	0.0251 (3)
H8	0.5183	0.5606	0.6085	0.03*
C9	0.66817 (17)	0.45213 (14)	0.70352 (12)	0.0242 (3)
C10	0.68615 (17)	0.34612 (13)	0.74146 (12)	0.0237 (3)
C11	0.56076 (19)	0.50205 (13)	0.85013 (13)	0.0269 (4)
C12	0.42375 (19)	0.32289 (14)	0.82151 (13)	0.0295 (4)
C13	0.29284 (19)	0.48252 (14)	0.70530 (13)	0.0298 (4)
C71	0.17072 (19)	0.37892 (16)	0.45371 (13)	0.0335 (4)
H71A	0.2029	0.3181	0.4255	0.05*
H71B	0.0894	0.4179	0.401	0.05*
H71C	0.1349	0.3518	0.5013	0.05*
O1	0.61634 (16)	0.55726 (10)	0.91861 (10)	0.0436 (4)
O2	0.39278 (16)	0.26735 (12)	0.87217 (10)	0.0486 (4)
O3	0.17872 (15)	0.52563 (12)	0.67906 (11)	0.0482 (4)
O5	0.77684 (12)	0.52853 (9)	0.73998 (9)	0.0305 (3)
O7	0.29490 (12)	0.45045 (10)	0.50235 (8)	0.0303 (3)
Cr	0.47389 (3)	0.413031 (19)	0.743218 (18)	0.01990 (9)

	U11	U22	U33	U12	U13	U23
C1'	0.0229 (8)	0.0363 (9)	0.0193 (8)	−0.0040 (7)	0.0096 (7)	0.0017 (7)
C2'	0.0282 (9)	0.0401 (10)	0.0317 (10)	−0.0012 (8)	0.0152 (8)	0.0017 (8)
C2	0.0198 (8)	0.0364 (9)	0.0228 (8)	−0.0006 (7)	0.0077 (7)	0.0013 (7)
C3'	0.0494 (11)	0.0344 (10)	0.0391 (11)	−0.0015 (9)	0.0259 (10)	0.0000 (8)
C3	0.0239 (8)	0.0319 (9)	0.0230 (8)	0.0030 (7)	0.0062 (7)	0.0046 (7)
C4	0.0241 (8)	0.0281 (8)	0.0265 (9)	0.0044 (7)	0.0079 (7)	0.0039 (7)
C4'	0.0444 (11)	0.0425 (11)	0.0286 (10)	−0.0176 (9)	0.0170 (9)	−0.0023 (8)
C5'	0.0278 (9)	0.0524 (12)	0.0263 (9)	−0.0110 (9)	0.0100 (8)	0.0034 (8)
C5	0.0286 (8)	0.0203 (8)	0.0280 (9)	0.0025 (7)	0.0110 (7)	−0.0027 (6)
C6	0.0261 (8)	0.0254 (8)	0.0256 (8)	−0.0011 (7)	0.0092 (7)	−0.0063 (7)
C6'	0.0248 (8)	0.0389 (10)	0.0247 (9)	−0.0013 (7)	0.0105 (7)	0.0037 (7)
C7	0.0209 (8)	0.0331 (9)	0.0195 (8)	0.0020 (7)	0.0081 (6)	0.0009 (7)
C8	0.0243 (8)	0.0279 (8)	0.0232 (8)	−0.0002 (7)	0.0102 (7)	0.0061 (7)
C9	0.0211 (8)	0.0306 (8)	0.0216 (8)	−0.0023 (7)	0.0098 (7)	0.0017 (7)
C10	0.0229 (8)	0.0258 (8)	0.0227 (8)	0.0021 (6)	0.0101 (7)	−0.0003 (6)
C11	0.0281 (9)	0.0203 (8)	0.0292 (9)	0.0040 (7)	0.0090 (7)	0.0041 (7)
C12	0.0291 (9)	0.0308 (9)	0.0269 (9)	−0.0074 (7)	0.0104 (7)	−0.0030 (7)
C13	0.0274 (9)	0.0331 (9)	0.0280 (9)	−0.0003 (7)	0.0108 (7)	−0.0054 (7)
C71	0.0206 (8)	0.0466 (11)	0.0286 (9)	−0.0041 (8)	0.0058 (7)	0.0003 (8)
O1	0.0546 (9)	0.0264 (6)	0.0327 (7)	0.0063 (6)	0.0020 (7)	−0.0075 (6)
O2	0.0537 (9)	0.0537 (9)	0.0381 (8)	−0.0232 (7)	0.0195 (7)	0.0062 (7)
O3	0.0302 (7)	0.0592 (9)	0.0495 (9)	0.0148 (7)	0.0115 (7)	−0.0084 (7)
O5	0.0203 (6)	0.0333 (7)	0.0295 (6)	−0.0058 (5)	0.0024 (5)	0.0110 (5)
O7	0.0231 (6)	0.0369 (7)	0.0243 (6)	−0.0018 (5)	0.0037 (5)	0.0050 (5)
Cr	0.02079 (14)	0.01811 (14)	0.02113 (14)	−0.00032 (10)	0.00923 (11)	0.00022 (10)

C1'—C2'	1.385 (3)	C6—C7	1.401 (2)
C1'—C6'	1.393 (2)	C6—Cr	2.2350 (16)
C1'—C2	1.510 (2)	C6—H6	0.95
C2'—C3'	1.396 (3)	C6'—H6'	0.95
C2'—H2'	0.95	C7—O7	1.3558 (19)
C2—O5	1.4513 (19)	C7—C8	1.411 (2)
C2—C3	1.522 (2)	C7—Cr	2.2729 (16)
C2—H2	1	C8—C9	1.406 (2)
C3'—C4'	1.381 (3)	C8—Cr	2.2424 (16)
C3'—H3'	0.95	C8—H8	0.95
C3—C4	1.526 (2)	C9—O5	1.3568 (19)
C3—H3A	0.99	C9—C10	1.412 (2)
C3—H3B	0.99	C9—Cr	2.2838 (16)
C4—C10	1.505 (2)	C10—Cr	2.2580 (16)
C4—H4A	0.99	C11—O1	1.160 (2)
C4—H4B	0.99	C11—Cr	1.8319 (17)
C4'—C5'	1.375 (3)	C12—O2	1.159 (2)
C4'—H4'	0.95	C12—Cr	1.8344 (18)
C5'—C6'	1.378 (2)	C13—O3	1.151 (2)
C5'—H5'	0.95	C13—Cr	1.8376 (18)
C5—C6	1.407 (2)	C71—O7	1.433 (2)
C5—C10	1.408 (2)	C71—H71A	0.98
C5—Cr	2.1808 (16)	C71—H71B	0.98
C5—H5	0.95	C71—H71C	0.98
C2'—C1'—C6'	118.91 (16)	O5—C9—C8	115.42 (14)
C2'—C1'—C2	122.96 (15)	O5—C9—C10	122.93 (14)
C6'—C1'—C2	118.12 (15)	C8—C9—C10	121.58 (15)
C1'—C2'—C3'	120.00 (16)	O5—C9—Cr	130.27 (11)
C1'—C2'—H2'	120	C8—C9—Cr	70.31 (9)
C3'—C2'—H2'	120	C10—C9—Cr	70.90 (9)
O5—C2—C1'	106.96 (13)	C5—C10—C9	116.89 (14)
O5—C2—C3	110.32 (13)	C5—C10—C4	122.62 (14)
C1'—C2—C3	113.95 (14)	C9—C10—C4	120.46 (14)
O5—C2—H2	108.5	C5—C10—Cr	68.55 (9)
C1'—C2—H2	108.5	C9—C10—Cr	72.88 (9)
C3—C2—H2	108.5	C4—C10—Cr	130.77 (11)
C4'—C3'—C2'	120.27 (18)	O1—C11—Cr	179.12 (15)
C4'—C3'—H3'	119.9	O2—C12—Cr	178.82 (16)
C2'—C3'—H3'	119.9	O3—C13—Cr	178.24 (16)
C2—C3—C4	109.51 (14)	O7—C71—H71A	109.5
C2—C3—H3A	109.8	O7—C71—H71B	109.5
C4—C3—H3A	109.8	H71A—C71—H71B	109.5
C2—C3—H3B	109.8	O7—C71—H71C	109.5
C4—C3—H3B	109.8	H71A—C71—H71C	109.5
H3A—C3—H3B	108.2	H71B—C71—H71C	109.5
C10—C4—C3	110.43 (13)	C9—O5—C2	117.07 (12)
C10—C4—H4A	109.6	C7—O7—C71	117.83 (13)
C3—C4—H4A	109.6	C11—Cr—C12	87.55 (7)
C10—C4—H4B	109.6	C11—Cr—C13	91.11 (7)
C3—C4—H4B	109.6	C12—Cr—C13	89.65 (8)
H4A—C4—H4B	108.1	C11—Cr—C5	130.80 (7)
C5'—C4'—C3'	119.72 (18)	C12—Cr—C5	89.36 (7)
C5'—C4'—H4'	120.1	C13—Cr—C5	137.98 (7)
C3'—C4'—H4'	120.1	C11—Cr—C6	164.20 (7)
C4'—C5'—C6'	120.35 (17)	C12—Cr—C6	100.73 (7)
C4'—C5'—H5'	119.8	C13—Cr—C6	102.28 (7)
C6'—C5'—H5'	119.8	C5—Cr—C6	37.14 (6)
C6—C5—C10	122.61 (15)	C11—Cr—C8	104.82 (7)
C6—C5—Cr	73.52 (9)	C12—Cr—C8	166.28 (7)
C10—C5—Cr	74.51 (9)	C13—Cr—C8	95.93 (7)
C6—C5—H5	118.7	C5—Cr—C8	78.10 (6)
C10—C5—H5	118.7	C6—Cr—C8	65.85 (6)
Cr—C5—H5	125	C11—Cr—C10	98.15 (7)
C7—C6—C5	119.02 (15)	C12—Cr—C10	106.65 (7)
C7—C6—Cr	73.38 (9)	C13—Cr—C10	161.49 (7)
C5—C6—Cr	69.34 (9)	C5—Cr—C10	36.94 (6)
C7—C6—H6	120.5	C6—Cr—C10	66.68 (6)
C5—C6—H6	120.5	C8—Cr—C10	66.26 (6)
Cr—C6—H6	129	C11—Cr—C7	139.56 (7)
C5'—C6'—C1'	120.73 (17)	C12—Cr—C7	132.48 (7)
C5'—C6'—H6'	119.6	C13—Cr—C7	84.71 (7)
C1'—C6'—H6'	119.6	C5—Cr—C7	65.78 (6)
O7—C7—C6	124.88 (15)	C6—Cr—C7	36.20 (6)
O7—C7—C8	115.21 (14)	C8—Cr—C7	36.40 (6)
C6—C7—C8	119.89 (14)	C10—Cr—C7	77.84 (6)
O7—C7—Cr	130.14 (11)	C11—Cr—C9	88.31 (7)
C6—C7—Cr	70.42 (9)	C12—Cr—C9	141.22 (7)
C8—C7—Cr	70.62 (9)	C13—Cr—C9	128.98 (7)
C9—C8—C7	119.56 (15)	C5—Cr—C9	65.09 (6)
C9—C8—Cr	73.51 (9)	C6—Cr—C9	76.78 (6)
C7—C8—Cr	72.98 (9)	C8—Cr—C9	36.18 (6)
C9—C8—H8	120.2	C10—Cr—C9	36.22 (6)
C7—C8—H8	120.2	C7—Cr—C9	64.57 (6)
Cr—C8—H8	124.9
C6'—C1'—C2'—C3'	−0.4 (3)	C7—C6—Cr—C9	−64.80 (10)
C2—C1'—C2'—C3'	178.97 (16)	C5—C6—Cr—C9	66.02 (10)
C2'—C1'—C2—O5	17.3 (2)	C9—C8—Cr—C11	65.59 (11)
C6'—C1'—C2—O5	−163.39 (14)	C7—C8—Cr—C11	−165.45 (10)
C2'—C1'—C2—C3	−104.93 (18)	C9—C8—Cr—C12	−88.2 (3)
C6'—C1'—C2—C3	74.42 (19)	C7—C8—Cr—C12	40.8 (3)
C1'—C2'—C3'—C4'	−0.5 (3)	C9—C8—Cr—C13	158.32 (10)
O5—C2—C3—C4	61.99 (17)	C7—C8—Cr—C13	−72.72 (10)
C1'—C2—C3—C4	−177.69 (14)	C9—C8—Cr—C5	−63.83 (10)
C2—C3—C4—C10	−47.68 (18)	C7—C8—Cr—C5	65.13 (10)
C2'—C3'—C4'—C5'	0.6 (3)	C9—C8—Cr—C6	−100.86 (11)
C3'—C4'—C5'—C6'	0.3 (3)	C7—C8—Cr—C6	28.10 (9)
C10—C5—C6—C7	−2.7 (2)	C9—C8—Cr—C10	−26.92 (10)
Cr—C5—C6—C7	56.02 (14)	C7—C8—Cr—C10	102.04 (10)
C10—C5—C6—Cr	−58.68 (14)	C9—C8—Cr—C7	−128.96 (15)
C4'—C5'—C6'—C1'	−1.2 (3)	C7—C8—Cr—C9	128.96 (15)
C2'—C1'—C6'—C5'	1.2 (3)	C5—C10—Cr—C11	155.21 (10)
C2—C1'—C6'—C5'	−178.16 (16)	C9—C10—Cr—C11	−75.77 (10)
C5—C6—C7—O7	−179.96 (15)	C4—C10—Cr—C11	40.00 (16)
Cr—C6—C7—O7	−125.88 (16)	C5—C10—Cr—C12	65.34 (11)
C5—C6—C7—C8	−1.7 (2)	C9—C10—Cr—C12	−165.64 (10)
Cr—C6—C7—C8	52.36 (14)	C4—C10—Cr—C12	−49.87 (16)
C5—C6—C7—Cr	−54.07 (13)	C5—C10—Cr—C13	−85.5 (2)
O7—C7—C8—C9	−174.85 (14)	C9—C10—Cr—C13	43.5 (3)
C6—C7—C8—C9	6.7 (2)	C4—C10—Cr—C13	159.3 (2)
Cr—C7—C8—C9	59.01 (14)	C9—C10—Cr—C5	129.02 (14)
O7—C7—C8—Cr	126.14 (13)	C4—C10—Cr—C5	−115.21 (18)
C6—C7—C8—Cr	−52.27 (14)	C5—C10—Cr—C6	−29.40 (9)
C7—C8—C9—O5	175.10 (14)	C9—C10—Cr—C6	99.61 (10)
Cr—C8—C9—O5	−126.16 (14)	C4—C10—Cr—C6	−144.62 (16)
C7—C8—C9—C10	−7.7 (2)	C5—C10—Cr—C8	−102.12 (10)
Cr—C8—C9—C10	51.09 (14)	C9—C10—Cr—C8	26.90 (9)
C7—C8—C9—Cr	−58.74 (14)	C4—C10—Cr—C8	142.67 (16)
C6—C5—C10—C9	1.9 (2)	C5—C10—Cr—C7	−65.70 (10)
Cr—C5—C10—C9	−56.37 (13)	C9—C10—Cr—C7	63.32 (10)
C6—C5—C10—C4	−176.23 (15)	C4—C10—Cr—C7	179.09 (16)
Cr—C5—C10—C4	125.55 (15)	C5—C10—Cr—C9	−129.02 (14)
C6—C5—C10—Cr	58.22 (14)	C4—C10—Cr—C9	115.77 (18)
O5—C9—C10—C5	−179.62 (15)	O7—C7—Cr—C11	−85.11 (17)
C8—C9—C10—C5	3.3 (2)	C6—C7—Cr—C11	155.29 (11)
Cr—C9—C10—C5	54.18 (13)	C8—C7—Cr—C11	21.99 (14)
O5—C9—C10—C4	−1.5 (2)	O7—C7—Cr—C12	85.04 (17)
C8—C9—C10—C4	−178.53 (15)	C6—C7—Cr—C12	−34.57 (13)
Cr—C9—C10—C4	−127.70 (15)	C8—C7—Cr—C12	−167.87 (11)
O5—C9—C10—Cr	126.20 (16)	O7—C7—Cr—C13	0.38 (15)
C8—C9—C10—Cr	−50.83 (14)	C6—C7—Cr—C13	−119.22 (11)
C3—C4—C10—C5	−163.05 (15)	C8—C7—Cr—C13	107.48 (11)
C3—C4—C10—C9	18.9 (2)	O7—C7—Cr—C5	149.67 (16)
C3—C4—C10—Cr	−74.28 (18)	C6—C7—Cr—C5	30.06 (9)
C8—C9—O5—C2	−167.67 (14)	C8—C7—Cr—C5	−103.24 (10)
C10—C9—O5—C2	15.1 (2)	O7—C7—Cr—C6	119.60 (19)
Cr—C9—O5—C2	107.28 (16)	C8—C7—Cr—C6	−133.30 (14)
C1'—C2—O5—C9	−169.74 (13)	O7—C7—Cr—C8	−107.10 (18)
C3—C2—O5—C9	−45.31 (19)	C6—C7—Cr—C8	133.30 (14)
C6—C7—O7—C71	1.2 (2)	O7—C7—Cr—C10	−173.42 (16)
C8—C7—O7—C71	−177.07 (14)	C6—C7—Cr—C10	66.97 (10)
Cr—C7—O7—C71	−91.82 (17)	C8—C7—Cr—C10	−66.33 (10)
C6—C5—Cr—C11	−164.93 (10)	O7—C7—Cr—C9	−137.65 (16)
C10—C5—Cr—C11	−33.24 (13)	C6—C7—Cr—C9	102.75 (10)
C6—C5—Cr—C12	108.86 (11)	C8—C7—Cr—C9	−30.55 (9)
C10—C5—Cr—C12	−119.45 (10)	O5—C9—Cr—C11	−11.15 (14)
C6—C5—Cr—C13	20.10 (15)	C8—C9—Cr—C11	−118.27 (11)
C10—C5—Cr—C13	151.78 (11)	C10—C9—Cr—C11	106.27 (10)
C10—C5—Cr—C6	131.69 (15)	O5—C9—Cr—C12	−95.13 (17)
C6—C5—Cr—C8	−65.53 (10)	C8—C9—Cr—C12	157.75 (12)
C10—C5—Cr—C8	66.16 (10)	C10—C9—Cr—C12	22.30 (15)
C6—C5—Cr—C10	−131.69 (15)	O5—C9—Cr—C13	78.91 (16)
C6—C5—Cr—C7	−29.35 (10)	C8—C9—Cr—C13	−28.21 (13)
C10—C5—Cr—C7	102.34 (10)	C10—C9—Cr—C13	−163.67 (10)
C6—C5—Cr—C9	−101.28 (11)	O5—C9—Cr—C5	−148.41 (16)
C10—C5—Cr—C9	30.41 (9)	C8—C9—Cr—C5	104.47 (11)
C7—C6—Cr—C11	−84.6 (3)	C10—C9—Cr—C5	−30.99 (9)
C5—C6—Cr—C11	46.3 (3)	O5—C9—Cr—C6	174.13 (15)
C7—C6—Cr—C12	154.79 (10)	C8—C9—Cr—C6	67.01 (10)
C5—C6—Cr—C12	−74.38 (11)	C10—C9—Cr—C6	−68.45 (10)
C7—C6—Cr—C13	62.79 (11)	O5—C9—Cr—C8	107.12 (18)
C5—C6—Cr—C13	−166.38 (11)	C10—C9—Cr—C8	−135.45 (15)
C7—C6—Cr—C5	−130.82 (15)	O5—C9—Cr—C10	−117.42 (18)
C7—C6—Cr—C8	−28.25 (9)	C8—C9—Cr—C10	135.45 (15)
C5—C6—Cr—C8	102.57 (11)	O5—C9—Cr—C7	137.85 (16)
C7—C6—Cr—C10	−101.56 (10)	C8—C9—Cr—C7	30.73 (10)
C5—C6—Cr—C10	29.26 (9)	C10—C9—Cr—C7	−104.73 (10)
C5—C6—Cr—C7	130.82 (15)