{(S)-2-[({2-[1-(Anthracen-9-ylmeth-yl)pyrrolidine-2-carboxamido]-phen-yl}(phen-yl)methyl-idene)amino]-acetato(2-)-κ(4)N,N',N'',O(1)}nickel(II).

The title compound, [Ni(C(35)H(29)N(3)O(3))], includes a Schiff base ligand derived from (S)-1-[(anthracen-9-yl)meth-yl]-N-(2-benz-oyl-phen-yl)pyrrolidine-2-carboxamide and glycine. The Ni(II) atom is coordinated by three N atoms [Ni-N = 1.937 (3), 1.850 (3) and 1.850 (3) Å] and one O atom [Ni-O = 1.859 (2) Å], resulting in a pseudo-square-planar coordination environment.

Related literature

For preparation and evaluation of similar compounds in model reactions, see: Belokon et al. (1988 ▶); Kožíšek et al. (2004 ▶); Popkov et al. (2002 ▶, 2010 ▶). For an overview of application procedures, see: Popkov et al. (2005 ▶) and works cited therein. For NMR in solutions and similar highly unusual long-range spin–spin inter­actions, see: Jirman et al. (1998 ▶); Langer et al. (2007 ▶); Popkov et al. (1998 ▶, 2003 ▶). For the review of applications in positron emission tomography (PET), see: Popkov & De Spiegeleer (2012 ▶).

Experimental

Crystal data

[Ni(C35H29N3O3)]

M = 598.32

Orthorhombic,

a = 8.9080 (5) Å

b = 16.5249 (12) Å

c = 18.6981 (13) Å

V = 2752.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.75 mm−1

T = 150 K

0.31 × 0.26 × 0.14 mm

Data collection

Bruker–Nonius KappaCCD area-detector diffractometer

Absorption correction: Gaussian (Coppens, 1970 ▶) T min = 0.856, T max = 0.925

23768 measured reflections

6120 independent reflections

5037 reflections with I > 2σ(I)

R int = 0.071

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.087

S = 1.19

6120 reflections

379 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.38 e Å−3

Absolute structure: Flack (1983 ▶), 2615 Friedel pairs

Flack parameter: −0.019 (14)

Data collection: COLLECT (Hooft, 1998 ▶) and DENZO (Otwin­owski & Minor, 1997 ▶); cell refinement: COLLECT and DENZO; data reduction: COLLECT and DENZO; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812026827/im2378sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812026827/im2378Isup2.hkl

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

[Ni(C35H29N3O3)]	F(000) = 1248
Mr = 598.32	Dx = 1.444 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 23827 reflections
a = 8.9080 (5) Å	θ = 1–27.5°
b = 16.5249 (12) Å	µ = 0.75 mm−1
c = 18.6981 (13) Å	T = 150 K
V = 2752.4 (3) Å3	Block, red
Z = 4	0.31 × 0.26 × 0.14 mm

Bruker–Nonius KappaCCD area-detector diffractometer	6120 independent reflections
Radiation source: fine-focus sealed tube	5037 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.071
Detector resolution: 9.091 pixels mm-1	θmax = 27.5°, θmin = 1.6°
φ and ω scans to fill the Ewald sphere	h = −11→10
Absorption correction: gaussian (Coppens, 1970)	k = −19→21
Tmin = 0.856, Tmax = 0.925	l = −22→24
23768 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044	H-atom parameters constrained
wR(F2) = 0.087	w = 1/[σ2(Fo2) + (0.0124P)2 + 2.2393P] where P = (Fo2 + 2Fc2)/3
S = 1.19	(Δ/σ)max = 0.001
6120 reflections	Δρmax = 0.32 e Å−3
379 parameters	Δρmin = −0.38 e Å−3
0 restraints	Absolute structure: Flack (1983), 2615 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.019 (14)

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.

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 > 2sigma(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
Ni1	0.24182 (5)	0.29142 (2)	0.341302 (19)	0.01922 (9)
O2	0.3360 (2)	0.30227 (14)	0.42952 (11)	0.0254 (5)
N3	0.0779 (3)	0.34255 (16)	0.38193 (14)	0.0205 (6)
N1	0.4180 (3)	0.24291 (16)	0.29833 (14)	0.0210 (6)
N2	0.1482 (3)	0.27289 (15)	0.25450 (14)	0.0211 (6)
O3	0.2972 (2)	0.34356 (15)	0.54199 (12)	0.0308 (6)
O1	0.1528 (3)	0.17305 (14)	0.16634 (15)	0.0376 (6)
C7	−0.0029 (4)	0.3172 (2)	0.15323 (19)	0.0258 (7)
H7	0.0546	0.2854	0.1227	0.031*
C14	−0.2558 (4)	0.36460 (18)	0.43374 (16)	0.0243 (6)
H14	−0.2499	0.3085	0.4308	0.029*
C5	0.2084 (3)	0.2090 (2)	0.21725 (17)	0.0246 (7)
C20	0.2548 (4)	0.33210 (17)	0.48055 (15)	0.0226 (6)
C18	−0.1673 (4)	0.4966 (2)	0.3992 (2)	0.0295 (8)
H18	−0.1027	0.5289	0.3726	0.035*
C12	−0.0396 (3)	0.37223 (18)	0.34982 (18)	0.0210 (7)
C13	−0.1571 (4)	0.41254 (19)	0.39428 (17)	0.0210 (7)
C6	0.0284 (4)	0.3172 (2)	0.22744 (18)	0.0216 (7)
C21	0.5180 (3)	0.3056 (2)	0.26366 (17)	0.0249 (7)
H21A	0.5682	0.3362	0.3009	0.030*
H21B	0.5947	0.2777	0.2364	0.030*
C4	0.3570 (4)	0.18159 (19)	0.24694 (18)	0.0248 (7)
H4	0.4284	0.1733	0.2078	0.030*
C22	0.4380 (4)	0.3641 (2)	0.21447 (18)	0.0258 (8)
C2	0.4126 (4)	0.1213 (2)	0.36427 (19)	0.0315 (8)
H2A	0.3359	0.1345	0.3992	0.038*
H2B	0.4709	0.0757	0.3816	0.038*
C15	−0.3628 (4)	0.4004 (2)	0.47780 (19)	0.0300 (8)
H15	−0.4290	0.3684	0.5039	0.036*
C11	−0.0600 (4)	0.36713 (19)	0.27272 (17)	0.0210 (7)
C9	−0.2021 (4)	0.4135 (2)	0.16876 (19)	0.0297 (8)
H9	−0.2780	0.4452	0.1493	0.036*
C1	0.5114 (3)	0.1935 (2)	0.34910 (18)	0.0258 (7)
H1A	0.5331	0.2235	0.3925	0.031*
H1B	0.6051	0.1771	0.3270	0.031*
C16	−0.3702 (4)	0.4840 (2)	0.4825 (2)	0.0352 (9)
H16	−0.4409	0.5080	0.5123	0.042*
C8	−0.1158 (4)	0.3641 (2)	0.12543 (19)	0.0291 (8)
H8	−0.1348	0.3628	0.0765	0.035*
C30	0.3486 (5)	0.4049 (2)	0.0956 (2)	0.0354 (9)
C10	−0.1745 (4)	0.4141 (2)	0.24071 (19)	0.0262 (7)
H10	−0.2332	0.4471	0.2697	0.031*
C24	0.3850 (5)	0.4572 (2)	0.3174 (2)	0.0379 (10)
H24	0.4428	0.4251	0.3476	0.045*
C35	0.4320 (4)	0.3507 (2)	0.13999 (18)	0.0276 (8)
C19	0.0938 (4)	0.3502 (2)	0.45967 (17)	0.0264 (8)
H19A	0.0265	0.3128	0.4835	0.032*
H19B	0.0678	0.4047	0.4743	0.032*
C34	0.5118 (4)	0.2865 (3)	0.10405 (19)	0.0364 (8)
H34	0.5675	0.2500	0.1310	0.044*
C28	0.2807 (4)	0.4858 (2)	0.1981 (2)	0.0341 (9)
C23	0.3690 (4)	0.4337 (2)	0.2440 (2)	0.0283 (8)
C3	0.3427 (4)	0.1027 (2)	0.2911 (2)	0.0319 (8)
H3A	0.2380	0.0877	0.2963	0.038*
H3B	0.3956	0.0586	0.2679	0.038*
C17	−0.2732 (5)	0.5318 (2)	0.4430 (2)	0.0355 (9)
H17	−0.2786	0.5878	0.4464	0.043*
C25	0.3180 (5)	0.5244 (2)	0.3438 (3)	0.0540 (12)
H25	0.3341	0.5394	0.3911	0.065*
C33	0.5074 (5)	0.2784 (3)	0.0321 (2)	0.0535 (12)
H33	0.5601	0.2363	0.0107	0.064*
C31	0.3485 (6)	0.3928 (3)	0.0199 (2)	0.0557 (13)
H31	0.2938	0.4279	−0.0089	0.067*
C29	0.2727 (5)	0.4695 (2)	0.1259 (2)	0.0407 (10)
H29	0.2140	0.5025	0.0969	0.049*
C26	0.2233 (6)	0.5723 (3)	0.2992 (3)	0.0592 (15)
H26	0.1728	0.6165	0.3183	0.071*
C27	0.2067 (4)	0.5540 (2)	0.2292 (3)	0.0501 (12)
H27	0.1455	0.5864	0.2009	0.060*
C32	0.4254 (6)	0.3324 (3)	−0.0107 (2)	0.0650 (15)
H32	0.4247	0.3262	−0.0601	0.078*

	U11	U22	U33	U12	U13	U23
Ni1	0.02184 (17)	0.02218 (17)	0.01363 (16)	0.0019 (2)	−0.00030 (18)	−0.00127 (17)
O2	0.0269 (11)	0.0340 (14)	0.0153 (11)	0.0000 (11)	−0.0023 (9)	−0.0030 (11)
N3	0.0244 (14)	0.0227 (14)	0.0145 (14)	0.0016 (11)	0.0007 (11)	−0.0004 (11)
N1	0.0241 (14)	0.0218 (14)	0.0170 (14)	0.0009 (11)	0.0001 (11)	−0.0008 (11)
N2	0.0273 (14)	0.0218 (15)	0.0144 (13)	0.0023 (11)	−0.0034 (11)	−0.0012 (11)
O3	0.0336 (14)	0.0419 (15)	0.0170 (12)	−0.0017 (11)	−0.0014 (9)	−0.0034 (11)
O1	0.0482 (14)	0.0312 (13)	0.0334 (15)	0.0079 (11)	−0.0156 (13)	−0.0145 (12)
C7	0.0321 (17)	0.0277 (18)	0.0176 (17)	0.0001 (14)	−0.0030 (15)	−0.0016 (15)
C14	0.0232 (15)	0.0272 (15)	0.0225 (15)	−0.0020 (17)	−0.0029 (16)	0.0003 (12)
C5	0.0318 (18)	0.0224 (15)	0.0197 (15)	0.0027 (15)	−0.0005 (12)	−0.0036 (15)
C20	0.0284 (15)	0.0231 (14)	0.0162 (14)	0.0000 (17)	0.0001 (17)	0.0004 (11)
C18	0.0340 (19)	0.0246 (18)	0.030 (2)	0.0003 (16)	0.0079 (16)	0.0028 (16)
C12	0.0255 (15)	0.0153 (15)	0.0220 (18)	−0.0023 (13)	0.0019 (13)	0.0014 (14)
C13	0.0231 (16)	0.0236 (17)	0.0162 (16)	0.0008 (14)	−0.0005 (13)	0.0021 (13)
C6	0.0266 (17)	0.0208 (17)	0.0173 (17)	−0.0006 (13)	0.0010 (13)	−0.0006 (13)
C21	0.0230 (16)	0.032 (2)	0.0196 (17)	−0.0019 (15)	0.0011 (12)	−0.0032 (15)
C4	0.0278 (17)	0.0281 (18)	0.0184 (17)	0.0051 (14)	−0.0005 (14)	−0.0070 (14)
C22	0.0250 (17)	0.030 (2)	0.0228 (18)	−0.0053 (15)	0.0019 (14)	0.0034 (15)
C2	0.045 (2)	0.0235 (19)	0.026 (2)	0.0072 (16)	0.0020 (15)	0.0050 (14)
C15	0.0225 (17)	0.045 (2)	0.0225 (19)	−0.0059 (16)	0.0019 (14)	0.0027 (16)
C11	0.0227 (16)	0.0197 (17)	0.0206 (17)	−0.0029 (13)	−0.0010 (13)	0.0024 (13)
C9	0.0333 (18)	0.0305 (18)	0.025 (2)	0.0022 (14)	−0.0065 (14)	0.0060 (16)
C1	0.0287 (15)	0.0320 (19)	0.0165 (16)	0.0092 (14)	−0.0006 (13)	−0.0007 (15)
C16	0.0296 (19)	0.048 (2)	0.028 (2)	0.0051 (17)	0.0049 (16)	−0.0073 (18)
C8	0.037 (2)	0.032 (2)	0.0185 (17)	0.0005 (16)	−0.0059 (14)	0.0037 (15)
C30	0.044 (2)	0.032 (2)	0.029 (2)	−0.0119 (18)	−0.0077 (17)	0.0065 (17)
C10	0.0266 (17)	0.0279 (18)	0.0241 (19)	0.0023 (14)	0.0015 (14)	0.0037 (15)
C24	0.051 (2)	0.031 (2)	0.032 (2)	−0.0039 (18)	0.0139 (18)	−0.0006 (17)
C35	0.0278 (17)	0.035 (2)	0.0197 (19)	−0.0051 (15)	0.0012 (13)	0.0035 (14)
C19	0.0296 (18)	0.034 (2)	0.0156 (17)	0.0082 (15)	0.0003 (13)	−0.0015 (14)
C34	0.042 (2)	0.045 (2)	0.0228 (19)	−0.004 (2)	0.0042 (15)	−0.0018 (19)
C28	0.030 (2)	0.0249 (18)	0.047 (2)	−0.0092 (15)	0.0032 (17)	0.0067 (16)
C23	0.0252 (17)	0.0260 (18)	0.034 (2)	−0.0071 (15)	0.0066 (15)	0.0019 (16)
C3	0.033 (2)	0.0241 (18)	0.039 (2)	0.0053 (16)	−0.0028 (16)	−0.0011 (16)
C17	0.043 (2)	0.0275 (17)	0.037 (2)	0.0073 (18)	0.0062 (18)	−0.0041 (15)
C25	0.080 (3)	0.038 (2)	0.043 (3)	−0.004 (2)	0.029 (3)	−0.006 (2)
C33	0.070 (3)	0.062 (3)	0.028 (2)	−0.003 (3)	0.010 (2)	−0.008 (2)
C31	0.080 (3)	0.061 (3)	0.025 (2)	−0.013 (3)	−0.018 (2)	0.015 (2)
C29	0.042 (2)	0.035 (2)	0.046 (2)	−0.008 (2)	−0.013 (2)	0.0141 (17)
C26	0.067 (4)	0.033 (2)	0.077 (4)	0.005 (2)	0.039 (3)	−0.002 (2)
C27	0.041 (3)	0.033 (2)	0.076 (4)	−0.0018 (18)	0.014 (2)	0.013 (2)
C32	0.103 (4)	0.076 (4)	0.015 (2)	−0.019 (3)	−0.008 (2)	0.001 (2)

Ni1—N2	1.850 (3)	C15—H15	0.9300
Ni1—N3	1.850 (3)	C11—C10	1.415 (4)
Ni1—O2	1.859 (2)	C9—C10	1.368 (5)
Ni1—N1	1.937 (3)	C9—C8	1.383 (5)
O2—C20	1.295 (4)	C9—H9	0.9300
N3—C12	1.303 (4)	C1—H1A	0.9701
N3—C19	1.466 (4)	C1—H1B	0.9700
N1—C4	1.499 (4)	C16—C17	1.384 (5)
N1—C1	1.503 (4)	C16—H16	0.9300
N1—C21	1.512 (4)	C8—H8	0.9300
N2—C5	1.374 (4)	C30—C29	1.385 (6)
N2—C6	1.389 (4)	C30—C35	1.429 (5)
O3—C20	1.224 (4)	C30—C31	1.431 (6)
O1—C5	1.226 (4)	C10—H10	0.9300
C7—C8	1.372 (5)	C24—C25	1.354 (5)
C7—C6	1.415 (5)	C24—C23	1.433 (5)
C7—H7	0.9300	C24—H24	0.9299
C14—C15	1.392 (5)	C35—C34	1.442 (5)
C14—C13	1.395 (4)	C19—H19A	0.9701
C14—H14	0.9299	C19—H19B	0.9701
C5—C4	1.505 (4)	C34—C33	1.353 (5)
C20—C19	1.516 (5)	C34—H34	0.9301
C18—C17	1.378 (5)	C28—C29	1.379 (5)
C18—C13	1.394 (5)	C28—C27	1.429 (6)
C18—H18	0.9300	C28—C23	1.447 (5)
C12—C11	1.455 (4)	C3—H3A	0.9701
C12—C13	1.493 (4)	C3—H3B	0.9700
C6—C11	1.421 (4)	C17—H17	0.9299
C21—C22	1.513 (5)	C25—C26	1.426 (7)
C21—H21A	0.9700	C25—H25	0.9300
C21—H21B	0.9700	C33—C32	1.403 (7)
C4—C3	1.548 (5)	C33—H33	0.9300
C4—H4	0.9800	C31—C32	1.339 (7)
C22—C35	1.411 (5)	C31—H31	0.9300
C22—C23	1.417 (5)	C29—H29	0.9300
C2—C1	1.511 (5)	C26—C27	1.350 (7)
C2—C3	1.534 (5)	C26—H26	0.9300
C2—H2A	0.9701	C27—H27	0.9300
C2—H2B	0.9701	C32—H32	0.9300
C15—C16	1.386 (5)
N2—Ni1—N3	94.59 (12)	C10—C9—H9	120.7
N2—Ni1—O2	176.00 (11)	C8—C9—H9	120.5
N3—Ni1—O2	87.01 (11)	N1—C1—C2	103.0 (3)
N2—Ni1—N1	86.14 (11)	N1—C1—H1A	111.2
N3—Ni1—N1	177.26 (12)	C2—C1—H1A	111.3
O2—Ni1—N1	92.43 (11)	N1—C1—H1B	111.1
C20—O2—Ni1	116.0 (2)	C2—C1—H1B	111.1
C12—N3—C19	120.2 (3)	H1A—C1—H1B	109.2
C12—N3—Ni1	128.1 (2)	C17—C16—C15	120.4 (3)
C19—N3—Ni1	111.7 (2)	C17—C16—H16	119.9
C4—N1—C1	103.8 (2)	C15—C16—H16	119.8
C4—N1—C21	113.7 (3)	C7—C8—C9	121.2 (3)
C1—N1—C21	108.4 (2)	C7—C8—H8	119.5
C4—N1—Ni1	104.59 (19)	C9—C8—H8	119.2
C1—N1—Ni1	114.3 (2)	C29—C30—C35	120.0 (3)
C21—N1—Ni1	111.8 (2)	C29—C30—C31	120.8 (4)
C5—N2—C6	121.3 (3)	C35—C30—C31	119.2 (4)
C5—N2—Ni1	113.3 (2)	C9—C10—C11	122.8 (3)
C6—N2—Ni1	125.3 (2)	C9—C10—H10	118.5
C8—C7—C6	121.1 (3)	C11—C10—H10	118.7
C8—C7—H7	119.4	C25—C24—C23	121.8 (4)
C6—C7—H7	119.6	C25—C24—H24	119.4
C15—C14—C13	120.2 (3)	C23—C24—H24	118.8
C15—C14—H14	119.8	C22—C35—C30	119.6 (3)
C13—C14—H14	120.0	C22—C35—C34	123.8 (3)
O1—C5—N2	127.5 (3)	C30—C35—C34	116.5 (3)
O1—C5—C4	119.7 (3)	N3—C19—C20	109.3 (3)
N2—C5—C4	112.8 (3)	N3—C19—H19A	110.0
O3—C20—O2	125.3 (3)	C20—C19—H19A	109.9
O3—C20—C19	120.2 (3)	N3—C19—H19B	109.7
O2—C20—C19	114.4 (3)	C20—C19—H19B	109.6
C17—C18—C13	120.3 (3)	H19A—C19—H19B	108.3
C17—C18—H18	119.9	C33—C34—C35	121.5 (4)
C13—C18—H18	119.8	C33—C34—H34	119.4
N3—C12—C11	122.3 (3)	C35—C34—H34	119.2
N3—C12—C13	118.3 (3)	C29—C28—C27	121.9 (4)
C11—C12—C13	119.3 (3)	C29—C28—C23	119.6 (4)
C18—C13—C14	119.3 (3)	C27—C28—C23	118.5 (4)
C18—C13—C12	121.8 (3)	C22—C23—C24	123.3 (3)
C14—C13—C12	118.9 (3)	C22—C23—C28	119.2 (3)
N2—C6—C7	120.6 (3)	C24—C23—C28	117.5 (3)
N2—C6—C11	121.0 (3)	C2—C3—C4	105.9 (3)
C7—C6—C11	118.3 (3)	C2—C3—H3A	110.6
N1—C21—C22	114.9 (3)	C4—C3—H3A	110.4
N1—C21—H21A	108.8	C2—C3—H3B	110.5
C22—C21—H21A	108.6	C4—C3—H3B	110.7
N1—C21—H21B	108.4	H3A—C3—H3B	108.7
C22—C21—H21B	108.4	C18—C17—C16	120.2 (3)
H21A—C21—H21B	107.5	C18—C17—H17	119.7
N1—C4—C5	110.6 (3)	C16—C17—H17	120.0
N1—C4—C3	104.9 (3)	C24—C25—C26	120.1 (5)
C5—C4—C3	112.2 (3)	C24—C25—H25	119.8
N1—C4—H4	109.7	C26—C25—H25	120.0
C5—C4—H4	109.7	C34—C33—C32	121.3 (5)
C3—C4—H4	109.6	C34—C33—H33	119.2
C35—C22—C23	119.7 (3)	C32—C33—H33	119.5
C35—C22—C21	121.2 (3)	C32—C31—C30	121.8 (4)
C23—C22—C21	119.1 (3)	C32—C31—H31	119.1
C1—C2—C3	103.1 (3)	C30—C31—H31	119.1
C1—C2—H2A	111.0	C28—C29—C30	121.7 (4)
C3—C2—H2A	111.1	C28—C29—H29	119.1
C1—C2—H2B	111.3	C30—C29—H29	119.3
C3—C2—H2B	111.1	C27—C26—C25	120.5 (4)
H2A—C2—H2B	109.1	C27—C26—H26	119.7
C16—C15—C14	119.6 (3)	C25—C26—H26	119.8
C16—C15—H15	120.2	C26—C27—C28	121.4 (4)
C14—C15—H15	120.2	C26—C27—H27	119.2
C10—C11—C6	117.8 (3)	C28—C27—H27	119.5
C10—C11—C12	118.5 (3)	C31—C32—C33	119.8 (4)
C6—C11—C12	123.7 (3)	C31—C32—H32	120.1
C10—C9—C8	118.8 (3)	C33—C32—H32	120.1