The seven-membered nickelacycle [NiBr{o-CH=C(CF₃)C₆H₄CH₂PPh₂-κ²C,P}{PPh(CH₂Ph)₂}]

The crystal and molecular structures of the title compound, 3-bromo-3-(di­benzyl­phenyl­phospho­nio)-2,2-di­phenyl-5-trifluoromethyl-1H-benzo­[e][1,2]­phosphanickelepine, [NiBr(C₂₂H₁₇F₃P)(C₂₀H₁₉P)], which was obtained as the major regioisomer from insertion of HCCCF₃ into the Ni—C bond of the five-membered phosphanickelacycle [NiBr(o-C₆H₄CH₂PPh₂-κ²C,P){PPh(CH₂Ph)₂}], have been determined. Principal geometric data include the Ni—X bond lengths Ni—Br 2.3343 (4) Å, Ni—P 2.1867 (7) and 2.2094 (7) Å, and Ni—C 1.882 (3) Å, and the two trans angles P—Ni—P 171.55 (3)° and Br—Ni—C 176.88 (9)°.

Computing details

Data collection: COLLECT (Nonius BV, 1997); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Watkin et al., 2001); molecular graphics: CAMERON (Watkin et al., 1996); software used to prepare material for publication: CRYSTALS and maXus (Mackay et al., 1999).

(I)

Crystal data

C42H36BrF3NiP2	F(000) = 1632
Mr = 798.28	Dx = 1.463 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 58628 reflections
a = 18.3307 (2) Å	θ = 2.9–27.5°
b = 10.9887 (1) Å	µ = 1.77 mm^−1
c = 18.7279 (2) Å	T = 200 K
β = 106.1717 (7)°	Prism, orange
V = 3623.10 (6) Å^3	0.24 × 0.21 × 0.12 mm
Z = 4

Data collection

KappaCCD diffractometer	5217 reflections with I > 3σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.075
CCD scans	θmax = 27.5°, θmin = 2.9°
Absorption correction: integration Gaussian integration (Coppens, 1970)	h = −23→23
Tmin = 0.668, Tmax = 0.831	k = −13→14
71633 measured reflections	l = −24→24
8294 independent reflections

Refinement

Refinement on F	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.031	Chebychev polynomial with 3 parameters (Carruthers & Watkin, 1979): 0.650, 0.286 and0.339
wR(F^2) = 0.036	(Δ/σ)max = 0.001
S = 1.05	Δρmax = 0.73 e Å^−3
5217 reflections	Δρmin = −0.54 e Å^−3
447 parameters	Extinction correction: Larson (1970)
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 191 (18)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Ni1	0.191505 (17)	0.31524 (3)	0.951709 (17)	0.0298
Br1	0.104524 (15)	0.44827 (3)	0.875488 (17)	0.0453
P1	0.10451 (4)	0.21906 (6)	0.98931 (4)	0.0313
P2	0.29158 (4)	0.39606 (6)	0.92591 (4)	0.0358
C1	0.22934 (16)	0.0181 (2)	0.94918 (15)	0.0379
C2	0.25705 (19)	−0.0377 (3)	0.89492 (19)	0.0518
C3	0.2108 (2)	−0.1141 (3)	0.84242 (19)	0.0591
C4	0.1375 (2)	−0.1364 (3)	0.84341 (18)	0.0575
C5	0.10914 (17)	−0.0814 (3)	0.89652 (17)	0.0449
C6	0.15411 (16)	−0.0040 (2)	0.94971 (15)	0.0369
C7	0.27757 (15)	0.0967 (3)	1.00880 (16)	0.0397
C8	0.26259 (15)	0.2145 (2)	1.01725 (16)	0.0372
C9	0.12346 (15)	0.0556 (2)	1.00807 (15)	0.0372
C10	0.33860 (19)	0.0315 (3)	1.0648 (2)	0.0568
C11	0.00591 (15)	0.2138 (2)	0.93185 (14)	0.0362
C12	−0.00863 (17)	0.1673 (3)	0.85992 (16)	0.0440
C13	−0.08304 (19)	0.1470 (3)	0.81729 (18)	0.0517
C14	−0.14286 (17)	0.1744 (3)	0.84580 (19)	0.0528
C15	−0.12876 (17)	0.2229 (3)	0.91642 (18)	0.0492
C16	−0.05486 (15)	0.2430 (3)	0.95957 (16)	0.0395
C17	0.09796 (14)	0.2834 (2)	1.07643 (14)	0.0344
C18	0.09180 (15)	0.2123 (3)	1.13653 (15)	0.0393
C19	0.08415 (18)	0.2670 (3)	1.20051 (16)	0.0476
C20	0.08389 (19)	0.3924 (3)	1.20606 (17)	0.0513
C21	0.08972 (18)	0.4641 (3)	1.14733 (17)	0.0486
C22	0.09649 (16)	0.4103 (3)	1.08282 (16)	0.0409
C23	0.32788 (16)	0.2882 (3)	0.86904 (16)	0.0414
C24	0.28064 (19)	0.2598 (3)	0.79976 (18)	0.0527
C25	0.3028 (2)	0.1771 (3)	0.7543 (2)	0.0624
C26	0.3726 (2)	0.1200 (4)	0.7772 (2)	0.0629
C27	0.4198 (2)	0.1470 (3)	0.8470 (2)	0.0630
C28	0.39705 (17)	0.2316 (3)	0.89262 (18)	0.0487
C29	0.37385 (15)	0.4279 (3)	1.00427 (15)	0.0395
C30	0.35979 (16)	0.5166 (2)	1.06102 (15)	0.0398
C31	0.29280 (17)	0.5175 (3)	1.08283 (16)	0.0440
C32	0.28553 (17)	0.5938 (3)	1.13987 (17)	0.0459
C33	0.34436 (19)	0.6694 (3)	1.17485 (18)	0.0518
C34	0.4095 (2)	0.6707 (3)	1.1528 (2)	0.0588
C35	0.41738 (18)	0.5954 (3)	1.09725 (18)	0.0509
C36	0.27737 (15)	0.5392 (3)	0.87159 (16)	0.0412
C37	0.34838 (15)	0.5937 (3)	0.85925 (16)	0.0406
C38	0.37976 (17)	0.5463 (3)	0.80507 (17)	0.0474
C39	0.44533 (18)	0.5957 (3)	0.7943 (2)	0.0575
C40	0.48025 (18)	0.6930 (4)	0.8362 (2)	0.0608
C41	0.4494 (2)	0.7419 (3)	0.8891 (2)	0.0608
C42	0.38394 (18)	0.6920 (3)	0.90139 (18)	0.0508
F1	0.31173 (14)	−0.0608 (2)	1.09672 (15)	0.0967
F2	0.39044 (15)	−0.0183 (3)	1.03628 (17)	0.1126
F3	0.37703 (13)	0.0996 (2)	1.12142 (14)	0.0883
H21	0.31063	−0.0222	0.89432	0.0630*
H31	0.2312	−0.1526	0.80361	0.0711*
H41	0.1046	−0.1924	0.80586	0.0675*
H51	0.05560	−0.0974	0.89710	0.0513*
H91	0.16158	0.0463	1.05767	0.0448*
H92	0.07508	0.0143	1.00881	0.0448*
H121	0.03475	0.1490	0.83899	0.0504*
H131	−0.09299	0.1124	0.76609	0.0578*
H141	−0.19622	0.1590	0.81535	0.0586*
H151	−0.17227	0.2437	0.93663	0.0566*
H161	−0.04494	0.2785	1.01053	0.0463*
H181	0.09299	0.1216	1.13303	0.0458*
H191	0.07889	0.2158	1.24292	0.0569*
H201	0.07976	0.4316	1.25299	0.0617*
H211	0.08841	0.5548	1.15114	0.0599*
H221	0.10048	0.4622	1.04018	0.0501*
H241	0.22973	0.2998	0.78285	0.0608*
H251	0.2679	0.1588	0.7041	0.0750*
H261	0.3888	0.0609	0.7440	0.0770*
H271	0.4700	0.1050	0.8650	0.0777*
H281	0.43167	0.2514	0.94277	0.0593*
H291	0.39125	0.3493	1.03040	0.0459*
H292	0.41497	0.4619	0.98450	0.0459*
H311	0.24975	0.4633	1.05700	0.0508*
H321	0.23753	0.5930	1.15534	0.0536*
H331	0.33948	0.7230	1.21642	0.0602*
H341	0.4517	0.7273	1.1773	0.0701*
H351	0.46567	0.5965	1.08231	0.0604*
H361	0.25446	0.6006	0.89838	0.0501*
H362	0.24128	0.5222	0.82175	0.0501*
H381	0.35442	0.4758	0.77418	0.0569*
H391	0.46700	0.5610	0.7552	0.0694*
H401	0.52819	0.7271	0.8288	0.0715*
H411	0.4739	0.8144	0.9184	0.0674*
H421	0.36232	0.7264	0.94056	0.0591*
H81	0.2924 (17)	0.251 (3)	1.0582 (17)	0.037 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.02967 (16)	0.03002 (16)	0.03116 (16)	−0.00106 (13)	0.01104 (12)	0.00390 (12)
Br1	0.03471 (14)	0.04891 (18)	0.05261 (17)	0.00381 (12)	0.01280 (12)	0.01897 (13)
P1	0.0327 (3)	0.0317 (3)	0.0323 (3)	−0.0020 (3)	0.0136 (3)	0.0027 (2)
P2	0.0312 (3)	0.0377 (4)	0.0391 (4)	−0.0021 (3)	0.0107 (3)	0.0072 (3)
C1	0.0422 (14)	0.0305 (13)	0.0436 (14)	0.0026 (11)	0.0162 (12)	0.0051 (11)
C2	0.0579 (18)	0.0420 (16)	0.065 (2)	0.0111 (14)	0.0323 (16)	0.0080 (15)
C3	0.084 (2)	0.0480 (18)	0.0523 (19)	0.0085 (17)	0.0313 (18)	−0.0043 (15)
C4	0.081 (2)	0.0417 (16)	0.0474 (18)	−0.0023 (16)	0.0141 (17)	−0.0077 (14)
C5	0.0498 (16)	0.0354 (14)	0.0489 (16)	−0.0055 (12)	0.0129 (13)	−0.0007 (12)
C6	0.0439 (14)	0.0289 (13)	0.0395 (14)	0.0004 (11)	0.0143 (11)	0.005 (1)
C7	0.0349 (13)	0.0364 (14)	0.0478 (16)	−0.0001 (11)	0.0116 (12)	0.0093 (12)
C8	0.0362 (13)	0.0394 (14)	0.0366 (14)	−0.0081 (11)	0.0110 (11)	0.0015 (11)
C9	0.0383 (13)	0.0341 (13)	0.0420 (14)	−0.0024 (11)	0.0159 (11)	0.0041 (11)
C10	0.0452 (16)	0.0483 (18)	0.070 (2)	0.0014 (14)	0.0052 (15)	0.0147 (16)
C11	0.0381 (13)	0.0353 (14)	0.0361 (13)	−0.0032 (11)	0.0119 (11)	0.006 (1)
C12	0.0501 (16)	0.0436 (16)	0.0393 (15)	−0.0009 (13)	0.0139 (13)	0.0022 (12)
C13	0.0588 (19)	0.0441 (17)	0.0430 (16)	−0.0047 (14)	−0.0010 (14)	0.0051 (13)
C14	0.0407 (15)	0.0488 (17)	0.061 (2)	−0.0072 (13)	0.0006 (14)	0.0164 (15)
C15	0.0380 (14)	0.0518 (17)	0.0589 (19)	0.0021 (13)	0.0155 (14)	0.0189 (15)
C16	0.0368 (13)	0.0411 (15)	0.0424 (15)	−0.0000 (11)	0.0142 (11)	0.0098 (12)
C17	0.0323 (12)	0.0393 (14)	0.0335 (13)	−0.003 (1)	0.012 (1)	0.001 (1)
C18	0.0426 (14)	0.0409 (15)	0.0364 (14)	−0.0039 (12)	0.0145 (11)	0.0037 (11)
C19	0.0543 (17)	0.0559 (18)	0.0364 (15)	−0.0031 (14)	0.0187 (13)	0.0050 (13)
C20	0.0603 (19)	0.0560 (19)	0.0447 (16)	−0.0068 (15)	0.0265 (15)	−0.0080 (14)
C21	0.0582 (18)	0.0428 (16)	0.0526 (17)	−0.0044 (14)	0.0282 (15)	−0.0060 (13)
C22	0.0465 (15)	0.0382 (14)	0.0433 (15)	−0.0011 (12)	0.0215 (12)	0.0034 (12)
C23	0.0419 (14)	0.0400 (15)	0.0459 (15)	−0.0073 (12)	0.0181 (12)	0.0007 (12)
C24	0.0541 (18)	0.0556 (19)	0.0512 (18)	−0.0059 (15)	0.0194 (15)	−0.0113 (15)
C25	0.062 (2)	0.072 (2)	0.058 (2)	−0.0136 (18)	0.0238 (17)	−0.0256 (18)
C26	0.058 (2)	0.070 (2)	0.070 (2)	−0.0151 (18)	0.0338 (18)	−0.0271 (19)
C27	0.0478 (17)	0.062 (2)	0.086 (3)	−0.0021 (16)	0.0305 (18)	−0.0085 (19)
C28	0.0479 (16)	0.0515 (17)	0.0504 (17)	−0.0102 (14)	0.0198 (14)	−0.0086 (14)
C29	0.0355 (13)	0.0402 (15)	0.0434 (14)	−0.0019 (11)	0.0120 (11)	0.0007 (12)
C30	0.0475 (16)	0.0344 (14)	0.0388 (14)	0.0005 (12)	0.0140 (12)	0.0007 (11)
C31	0.0462 (15)	0.0416 (15)	0.0449 (15)	−0.0043 (13)	0.0136 (13)	−0.0035 (12)
C32	0.0470 (16)	0.0420 (15)	0.0510 (17)	0.0033 (13)	0.0173 (13)	−0.0017 (13)
C33	0.0611 (19)	0.0424 (16)	0.0508 (17)	−0.0025 (14)	0.0136 (15)	−0.0082 (13)
C34	0.060 (2)	0.0525 (19)	0.063 (2)	−0.0144 (16)	0.0158 (17)	−0.0120 (16)
C35	0.0456 (16)	0.0512 (18)	0.0572 (18)	−0.0069 (14)	0.0163 (14)	−0.0023 (15)
C36	0.0373 (13)	0.0419 (15)	0.0464 (15)	−0.0002 (12)	0.0150 (12)	0.0103 (12)
C37	0.0359 (13)	0.0397 (14)	0.0449 (15)	−0.0012 (12)	0.0091 (12)	0.0149 (12)
C38	0.0479 (16)	0.0482 (16)	0.0496 (16)	−0.0038 (13)	0.0196 (13)	0.0127 (14)
C39	0.0490 (17)	0.066 (2)	0.063 (2)	0.0022 (16)	0.0252 (16)	0.0259 (17)
C40	0.0403 (16)	0.077 (2)	0.064 (2)	−0.0061 (16)	0.0125 (15)	0.0314 (19)
C41	0.0551 (19)	0.056 (2)	0.061 (2)	−0.0176 (16)	−0.0007 (16)	0.0195 (17)
C42	0.0524 (17)	0.0467 (17)	0.0513 (17)	−0.0073 (14)	0.0110 (14)	0.0122 (14)
F1	0.0836 (16)	0.0679 (15)	0.113 (2)	−0.0135 (12)	−0.0149 (14)	0.0544 (14)
F2	0.0706 (16)	0.139 (3)	0.121 (2)	0.0623 (17)	0.0143 (15)	0.0209 (19)
F3	0.0766 (14)	0.0647 (13)	0.0889 (16)	−0.0049 (12)	−0.0343 (13)	0.0180 (12)

Geometric parameters (Å, º)

Ni1—Br1	2.3343 (4)	C19—H191	1.00
Ni1—P1	2.1867 (7)	C20—C21	1.381 (4)
Ni1—P2	2.2094 (7)	C20—H201	1.00
Ni1—C8	1.882 (3)	C21—C22	1.381 (4)
P1—C9	1.844 (3)	C21—H211	1.00
P1—C11	1.829 (3)	C22—H221	1.00
P1—C17	1.813 (3)	C23—C24	1.380 (4)
P2—C23	1.838 (3)	C23—C28	1.370 (4)
P2—C29	1.821 (3)	C24—C25	1.380 (4)
P2—C36	1.852 (3)	C24—H241	1.00
C1—C2	1.398 (4)	C25—C26	1.382 (5)
C1—C6	1.403 (4)	C25—H251	1.00
C1—C7	1.491 (4)	C26—C27	1.384 (5)
C2—C3	1.388 (5)	C26—H261	1.00
C2—H21	1.00	C27—C28	1.403 (5)
C3—C4	1.371 (5)	C27—H271	1.00
C3—H31	1.00	C28—H281	1.00
C4—C5	1.383 (4)	C29—C30	1.516 (4)
C4—H41	1.00	C29—H291	1.00
C5—C6	1.392 (4)	C29—H292	1.00
C5—H51	1.00	C30—C31	1.398 (4)
C6—C9	1.511 (4)	C30—C35	1.387 (4)
C7—C8	1.342 (4)	C31—C32	1.393 (4)
C7—C10	1.487 (4)	C31—H311	1.00
C8—H81	0.90 (3)	C32—C33	1.374 (4)
C9—H91	1.00	C32—H321	1.00
C9—H92	1.00	C33—C34	1.368 (5)
C10—F1	1.339 (4)	C33—H331	1.00
C10—F2	1.331 (4)	C34—C35	1.367 (5)
C10—F3	1.328 (4)	C34—H341	1.00
C11—C12	1.395 (4)	C35—H351	1.00
C11—C16	1.391 (4)	C36—C37	1.508 (4)
C12—C13	1.393 (4)	C36—H361	1.00
C12—H121	1.00	C36—H362	1.00
C13—C14	1.380 (5)	C37—C38	1.399 (4)
C13—H131	1.00	C37—C42	1.388 (4)
C14—C15	1.382 (5)	C38—C39	1.384 (4)
C14—H141	1.00	C38—H381	1.00
C15—C16	1.388 (4)	C39—C40	1.375 (5)
C15—H151	1.00	C39—H391	1.00
C16—H161	1.00	C40—C41	1.380 (5)
C17—C18	1.400 (4)	C40—H401	1.00
C17—C22	1.401 (4)	C41—C42	1.394 (5)
C18—C19	1.382 (4)	C41—H411	1.00
C18—H181	1.00	C42—H421	1.00
C19—C20	1.382 (5)
Br1—Ni1—P1	93.69 (2)	C18—C19—C20	120.1 (3)
Br1—Ni1—P2	94.70 (2)	C18—C19—H191	119.97 (17)
P1—Ni1—P2	171.55 (3)	C20—C19—H191	119.90 (17)
Br1—Ni1—C8	176.88 (9)	C19—C20—C21	120.4 (3)
P1—Ni1—C8	86.57 (8)	C19—C20—H201	119.83 (18)
P2—Ni1—C8	85.00 (8)	C21—C20—H201	119.77 (18)
Ni1—P1—C9	114.61 (9)	C20—C21—C22	119.9 (3)
Ni1—P1—C11	121.05 (8)	C20—C21—H211	120.18 (18)
C9—P1—C11	100.60 (12)	C22—C21—H211	119.89 (18)
Ni1—P1—C17	109.77 (8)	C17—C22—C21	120.6 (3)
C9—P1—C17	105.35 (12)	C17—C22—H221	119.43 (15)
C11—P1—C17	103.87 (12)	C21—C22—H221	119.97 (18)
Ni1—P2—C23	108.91 (9)	P2—C23—C24	117.2 (2)
Ni1—P2—C29	116.91 (9)	P2—C23—C28	123.9 (2)
C23—P2—C29	103.81 (13)	C24—C23—C28	118.9 (3)
Ni1—P2—C36	117.59 (9)	C23—C24—C25	120.9 (3)
C23—P2—C36	104.36 (13)	C23—C24—H241	118.95 (19)
C29—P2—C36	103.74 (13)	C25—C24—H241	120.2 (2)
C2—C1—C6	119.1 (3)	C24—C25—C26	120.9 (3)
C2—C1—C7	122.6 (3)	C24—C25—H251	119.5 (2)
C6—C1—C7	118.3 (2)	C26—C25—H251	119.6 (2)
C1—C2—C3	120.4 (3)	C25—C26—C27	118.5 (3)
C1—C2—H21	119.35 (19)	C25—C26—H261	120.8 (2)
C3—C2—H21	120.23 (19)	C27—C26—H261	120.7 (2)
C2—C3—C4	120.4 (3)	C26—C27—C28	120.2 (3)
C2—C3—H31	119.49 (19)	C26—C27—H271	119.6 (2)
C4—C3—H31	120.08 (19)	C28—C27—H271	120.2 (2)
C3—C4—C5	119.8 (3)	C23—C28—C27	120.7 (3)
C3—C4—H41	120.13 (19)	C23—C28—H281	119.51 (18)
C5—C4—H41	120.1 (2)	C27—C28—H281	119.8 (2)
C4—C5—C6	121.0 (3)	P2—C29—C30	115.09 (19)
C4—C5—H51	119.8 (2)	P2—C29—H291	107.94 (9)
C6—C5—H51	119.15 (17)	C30—C29—H291	107.79 (15)
C1—C6—C5	119.2 (3)	P2—C29—H292	108.28 (9)
C1—C6—C9	119.6 (2)	C30—C29—H292	108.18 (15)
C5—C6—C9	121.2 (2)	H291—C29—H292	109.467
C1—C7—C8	123.3 (3)	C29—C30—C31	123.0 (2)
C1—C7—C10	115.0 (2)	C29—C30—C35	119.3 (3)
C8—C7—C10	121.3 (3)	C31—C30—C35	117.6 (3)
Ni1—C8—C7	128.2 (2)	C30—C31—C32	120.5 (3)
Ni1—C8—H81	115.7 (19)	C30—C31—H311	119.57 (16)
C7—C8—H81	116.0 (19)	C32—C31—H311	119.91 (18)
P1—C9—C6	111.90 (18)	C31—C32—C33	119.9 (3)
P1—C9—H91	108.85 (9)	C31—C32—H321	119.77 (18)
C6—C9—H91	108.85 (15)	C33—C32—H321	120.28 (19)
P1—C9—H92	108.93 (8)	C32—C33—C34	119.8 (3)
C6—C9—H92	108.82 (14)	C32—C33—H331	119.92 (19)
H91—C9—H92	109.467	C34—C33—H331	120.28 (19)
C7—C10—F1	112.4 (3)	C33—C34—C35	120.6 (3)
C7—C10—F2	113.4 (3)	C33—C34—H341	119.74 (19)
F1—C10—F2	105.1 (3)	C35—C34—H341	119.61 (19)
C7—C10—F3	114.8 (3)	C30—C35—C34	121.5 (3)
F1—C10—F3	104.4 (3)	C30—C35—H351	118.89 (18)
F2—C10—F3	105.8 (3)	C34—C35—H351	119.6 (2)
P1—C11—C12	118.1 (2)	P2—C36—C37	115.23 (19)
P1—C11—C16	122.4 (2)	P2—C36—H361	108.15 (9)
C12—C11—C16	119.2 (3)	C37—C36—H361	108.07 (16)
C11—C12—C13	120.3 (3)	P2—C36—H362	108.0 (1)
C11—C12—H121	119.56 (17)	C37—C36—H362	107.82 (16)
C13—C12—H121	120.09 (19)	H361—C36—H362	109.467
C12—C13—C14	120.0 (3)	C36—C37—C38	120.6 (3)
C12—C13—H131	119.90 (19)	C36—C37—C42	120.7 (3)
C14—C13—H131	120.12 (19)	C38—C37—C42	118.7 (3)
C13—C14—C15	119.8 (3)	C37—C38—C39	120.6 (3)
C13—C14—H141	119.92 (19)	C37—C38—H381	119.32 (17)
C15—C14—H141	120.23 (18)	C39—C38—H381	120.1 (2)
C14—C15—C16	120.7 (3)	C38—C39—C40	120.4 (3)
C14—C15—H151	119.62 (18)	C38—C39—H391	119.7 (2)
C16—C15—H151	119.69 (18)	C40—C39—H391	119.8 (2)
C11—C16—C15	119.9 (3)	C39—C40—C41	119.6 (3)
C11—C16—H161	119.64 (16)	C39—C40—H401	119.9 (2)
C15—C16—H161	120.42 (18)	C41—C40—H401	120.5 (2)
P1—C17—C18	123.1 (2)	C40—C41—C42	120.6 (3)
P1—C17—C22	118.2 (2)	C40—C41—H411	119.4 (2)
C18—C17—C22	118.6 (2)	C42—C41—H411	120.0 (2)
C17—C18—C19	120.3 (3)	C37—C42—C41	120.1 (3)
C17—C18—H181	119.72 (16)	C37—C42—H421	119.46 (18)
C19—C18—H181	119.97 (17)	C41—C42—H421	120.4 (2)