Bis(triphenylphosphine)iminium bromide acetonitrile monosolvate.

The title compound, C(36)H(30)NP(2) (+)·Br(-)·C(2)H(3)N, crystallized from a CH(3)CN/OEt(2) solution as an acetonitrile solvate. The central P-N-P angle [142.88 (10)°] is significantly larger than in the corresponding chloride and iodide structures.

Related literature

Several bis­(triphenyl­phosphine)iminium halide structures have been determined. For [(Ph3P)2N]Cl, see: Knapp et al. (2010 ▶); for [(Ph3P)2N]Cl·B(OH)3, see: Andrews et al. (1983 ▶); for [(Ph3P)2N]Cl·CH3C6H5, see: Weller et al. (1993 ▶); for [(Ph3P)2N]Cl·CH2Cl2, see: Carroll et al. (1996 ▶); for [(Ph3P)2N]Cl·CH2Cl2·H2O, see: de Arellano (1997 ▶); for [(Ph3P)2N]I, see: Beckett et al. (2010 ▶). For a discussion of the [(Ph3P)2N]+ cation, see: Lewis et al. (2000 ▶). For the synthesis, see: Martinsen & Songstad (1977 ▶).

Experimental

Crystal data

C36H30NP2 +·Br−·C2H3N

M = 659.51

Orthorhombic,

a = 19.7113 (6) Å

b = 15.9564 (5) Å

c = 20.3318 (6) Å

V = 6394.8 (3) Å3

Z = 8

Mo Kα radiation

μ = 1.42 mm−1

T = 100 K

0.20 × 0.20 × 0.16 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.765, T max = 0.805

57718 measured reflections

7749 independent reflections

6140 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.085

S = 1.02

7749 reflections

391 parameters

Only H-atom displacement parameters refined

Δρmax = 0.51 e Å−3

Δρmin = −0.45 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg et al., 2010 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810046337/fi2100sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810046337/fi2100Isup2.hkl

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

C36H30NP2+·Br−·C2H3N	F(000) = 2720
Mr = 659.51	Dx = 1.370 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 9913 reflections
a = 19.7113 (6) Å	θ = 2.4–27.3°
b = 15.9564 (5) Å	µ = 1.42 mm−1
c = 20.3318 (6) Å	T = 100 K
V = 6394.8 (3) Å3	Block, colourless
Z = 8	0.20 × 0.20 × 0.16 mm

Bruker APEXII CCD area-detector diffractometer	7749 independent reflections
Radiation source: microfocus sealed tube	6140 reflections with I > 2σ(I)
multilayer mirro optics	Rint = 0.045
φ and ω scans	θmax = 28.1°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −26→21
Tmin = 0.765, Tmax = 0.805	k = −21→20
57718 measured reflections	l = −25→26

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) = 0.085	Only H-atom displacement parameters refined
S = 1.02	w = 1/[σ2(Fo2) + (0.0378P)2 + 4.5281P] where P = (Fo2 + 2Fc2)/3
7749 reflections	(Δ/σ)max < 0.001
391 parameters	Δρmax = 0.51 e Å−3
0 restraints	Δρmin = −0.45 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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
P1	0.25018 (2)	0.06051 (3)	0.17193 (2)	0.01189 (10)
N1	0.18271 (8)	0.01276 (9)	0.15375 (7)	0.0143 (3)
P2	0.12559 (2)	0.00609 (3)	0.09951 (2)	0.01196 (10)
C1	0.28765 (10)	0.12141 (11)	0.10725 (9)	0.0148 (4)
C2	0.25987 (10)	0.19901 (12)	0.09087 (9)	0.0190 (4)
H2	0.2253	0.2228	0.1176	0.0236 (11)*
C3	0.28261 (11)	0.24142 (13)	0.03571 (11)	0.0253 (5)
H3	0.2628	0.2935	0.0238	0.0236 (11)*
C4	0.33434 (12)	0.20749 (14)	−0.00204 (10)	0.0285 (5)
H4	0.3503	0.2368	−0.0397	0.0236 (11)*
C5	0.36285 (12)	0.13154 (14)	0.01468 (10)	0.0262 (5)
H5	0.3990	0.1095	−0.0110	0.0236 (11)*
C6	0.33941 (10)	0.08711 (12)	0.06833 (9)	0.0192 (4)
H6	0.3581	0.0339	0.0788	0.0236 (11)*
C7	0.23573 (10)	0.12855 (11)	0.24112 (9)	0.0144 (4)
C8	0.28104 (10)	0.19243 (12)	0.25734 (10)	0.0190 (4)
H8	0.3185	0.2041	0.2294	0.0236 (11)*
C9	0.27146 (11)	0.23902 (13)	0.31445 (10)	0.0251 (5)
H9	0.3020	0.2830	0.3253	0.0236 (11)*
C10	0.21734 (12)	0.22111 (13)	0.35532 (10)	0.0262 (5)
H10	0.2117	0.2517	0.3950	0.0236 (11)*
C11	0.17135 (12)	0.15921 (13)	0.33905 (10)	0.0244 (5)
H11	0.1336	0.1486	0.3669	0.0236 (11)*
C12	0.18020 (10)	0.11242 (12)	0.28210 (9)	0.0184 (4)
H12	0.1487	0.0696	0.2710	0.0236 (11)*
C13	0.31240 (9)	−0.01526 (11)	0.19747 (8)	0.0131 (4)
C14	0.37648 (10)	0.01108 (12)	0.21822 (9)	0.0181 (4)
H14	0.3871	0.0692	0.2192	0.0236 (11)*
C15	0.42468 (10)	−0.04721 (13)	0.23733 (9)	0.0204 (4)
H15	0.4683	−0.0291	0.2513	0.0236 (11)*
C16	0.40922 (11)	−0.13207 (12)	0.23604 (9)	0.0201 (4)
H16	0.4424	−0.1721	0.2489	0.0236 (11)*
C17	0.34575 (11)	−0.15843 (12)	0.21612 (10)	0.0203 (4)
H17	0.3352	−0.2165	0.2159	0.0236 (11)*
C18	0.29719 (10)	−0.10029 (12)	0.19634 (9)	0.0170 (4)
H18	0.2538	−0.1187	0.1821	0.0236 (11)*
C19	0.08890 (9)	−0.09672 (11)	0.10613 (9)	0.0127 (4)
C20	0.09094 (10)	−0.13784 (11)	0.16677 (9)	0.0159 (4)
H20	0.1147	−0.1138	0.2028	0.0236 (11)*
C21	0.05793 (10)	−0.21417 (12)	0.17393 (10)	0.0193 (4)
H21	0.0594	−0.2427	0.2149	0.0236 (11)*
C22	0.02288 (10)	−0.24900 (12)	0.12149 (10)	0.0212 (4)
H22	−0.0002	−0.3008	0.1270	0.0236 (11)*
C23	0.02120 (10)	−0.20880 (12)	0.06107 (10)	0.0204 (4)
H23	−0.0025	−0.2333	0.0252	0.0236 (11)*
C24	0.05428 (10)	−0.13253 (12)	0.05318 (9)	0.0171 (4)
H24	0.0533	−0.1048	0.0118	0.0236 (11)*
C25	0.05703 (9)	0.07942 (12)	0.11228 (9)	0.0146 (4)
C26	0.07040 (10)	0.16532 (12)	0.11015 (10)	0.0189 (4)
H26	0.1149	0.1845	0.1004	0.0236 (11)*
C27	0.01909 (10)	0.22260 (12)	0.12217 (9)	0.0200 (4)
H27	0.0285	0.2810	0.1207	0.0236 (11)*
C28	−0.04602 (10)	0.19508 (12)	0.13630 (9)	0.0186 (4)
H28	−0.0809	0.2345	0.1454	0.0236 (11)*
C29	−0.06021 (10)	0.10991 (13)	0.13709 (9)	0.0201 (4)
H29	−0.1050	0.0911	0.1458	0.0236 (11)*
C30	−0.00886 (10)	0.05211 (12)	0.12510 (9)	0.0168 (4)
H30	−0.0187	−0.0062	0.1257	0.0236 (11)*
C31	0.15659 (9)	0.02082 (11)	0.01724 (8)	0.0135 (4)
C32	0.21624 (10)	−0.02015 (12)	−0.00108 (9)	0.0185 (4)
H32	0.2388	−0.0557	0.0294	0.0236 (11)*
C33	0.24261 (11)	−0.00892 (13)	−0.06364 (9)	0.0230 (4)
H33	0.2834	−0.0365	−0.0760	0.0236 (11)*
C34	0.20953 (11)	0.04257 (13)	−0.10835 (10)	0.0243 (5)
H34	0.2276	0.0500	−0.1513	0.0236 (11)*
C35	0.15028 (11)	0.08313 (13)	−0.09059 (9)	0.0227 (4)
H35	0.1276	0.1181	−0.1214	0.0236 (11)*
C36	0.12382 (10)	0.07294 (12)	−0.02784 (9)	0.0178 (4)
H36	0.0834	0.1014	−0.0156	0.0236 (11)*
Br1	0.115207 (11)	0.361552 (13)	0.016157 (10)	0.02274 (7)
C37	0.01999 (12)	0.99644 (14)	0.40311 (11)	0.0289 (5)
H37A	−0.0050	1.0350	0.3744	0.045 (4)*
H37B	0.0460	1.0287	0.4355	0.045 (4)*
H37C	−0.0121	0.9597	0.4260	0.045 (4)*
C38	0.06723 (12)	0.94476 (13)	0.36271 (9)	0.0217 (4)
N2	0.10065 (10)	0.90568 (13)	0.33284 (9)	0.0323 (4)

	U11	U22	U33	U12	U13	U23
P1	0.0114 (2)	0.0112 (2)	0.0131 (2)	−0.00099 (19)	−0.00009 (17)	0.00014 (16)
N1	0.0126 (8)	0.0153 (8)	0.0150 (8)	−0.0022 (6)	−0.0023 (6)	0.0019 (6)
P2	0.0114 (2)	0.0114 (2)	0.0131 (2)	−0.00064 (18)	−0.00081 (17)	0.00066 (16)
C1	0.0138 (10)	0.0147 (9)	0.0161 (9)	−0.0044 (8)	0.0001 (7)	−0.0001 (7)
C2	0.0166 (10)	0.0158 (10)	0.0245 (10)	−0.0016 (8)	−0.0001 (8)	0.0019 (7)
C3	0.0261 (12)	0.0195 (10)	0.0304 (11)	−0.0051 (9)	−0.0050 (9)	0.0084 (8)
C4	0.0317 (13)	0.0328 (12)	0.0209 (10)	−0.0121 (11)	−0.0003 (9)	0.0069 (9)
C5	0.0249 (12)	0.0338 (13)	0.0199 (11)	−0.0031 (10)	0.0081 (8)	−0.0017 (8)
C6	0.0201 (11)	0.0181 (10)	0.0193 (10)	−0.0005 (8)	0.0007 (8)	−0.0029 (7)
C7	0.0151 (10)	0.0133 (9)	0.0148 (9)	0.0036 (7)	−0.0026 (7)	−0.0004 (7)
C8	0.0145 (10)	0.0167 (10)	0.0257 (10)	0.0027 (8)	−0.0035 (7)	−0.0034 (8)
C9	0.0236 (11)	0.0199 (11)	0.0318 (12)	0.0072 (9)	−0.0122 (9)	−0.0096 (8)
C10	0.0364 (13)	0.0244 (11)	0.0179 (10)	0.0156 (10)	−0.0057 (9)	−0.0058 (8)
C11	0.0295 (12)	0.0260 (11)	0.0177 (10)	0.0102 (10)	0.0045 (8)	0.0033 (8)
C12	0.0198 (11)	0.0170 (9)	0.0184 (10)	0.0008 (8)	0.0029 (7)	0.0027 (7)
C13	0.0132 (9)	0.0143 (9)	0.0117 (8)	0.0018 (7)	0.0006 (6)	0.0000 (7)
C14	0.0171 (10)	0.0165 (10)	0.0208 (10)	0.0000 (8)	−0.0003 (7)	−0.0033 (7)
C15	0.0140 (10)	0.0272 (11)	0.0198 (10)	0.0009 (9)	−0.0026 (7)	−0.0036 (8)
C16	0.0218 (11)	0.0209 (10)	0.0176 (10)	0.0078 (9)	−0.0001 (8)	0.0007 (7)
C17	0.0234 (11)	0.0141 (9)	0.0233 (10)	0.0024 (8)	0.0005 (8)	0.0015 (7)
C18	0.0149 (10)	0.0168 (9)	0.0192 (9)	−0.0005 (8)	0.0005 (7)	0.0004 (7)
C19	0.0094 (9)	0.0107 (9)	0.0181 (9)	0.0005 (7)	0.0010 (7)	−0.0006 (7)
C20	0.0119 (9)	0.0172 (9)	0.0185 (9)	0.0011 (8)	−0.0006 (7)	0.0000 (7)
C21	0.0157 (10)	0.0165 (10)	0.0257 (10)	0.0027 (8)	0.0033 (8)	0.0060 (8)
C22	0.0152 (10)	0.0132 (9)	0.0353 (11)	−0.0010 (8)	0.0036 (8)	0.0000 (8)
C23	0.0171 (10)	0.0162 (10)	0.0279 (11)	−0.0007 (8)	−0.0036 (8)	−0.0048 (8)
C24	0.0155 (10)	0.0168 (9)	0.0189 (10)	0.0023 (8)	−0.0019 (7)	−0.0015 (7)
C25	0.0147 (9)	0.0149 (9)	0.0142 (9)	−0.0001 (8)	−0.0011 (7)	−0.0003 (7)
C26	0.0149 (10)	0.0165 (9)	0.0254 (10)	−0.0004 (8)	0.0000 (8)	0.0005 (7)
C27	0.0229 (11)	0.0128 (9)	0.0242 (10)	0.0008 (8)	−0.0009 (8)	−0.0003 (7)
C28	0.0200 (11)	0.0194 (10)	0.0165 (9)	0.0050 (8)	0.0012 (7)	0.0003 (7)
C29	0.0162 (10)	0.0231 (10)	0.0210 (10)	0.0012 (9)	0.0038 (8)	0.0020 (8)
C30	0.0171 (10)	0.0153 (9)	0.0182 (9)	−0.0011 (8)	0.0014 (7)	0.0018 (7)
C31	0.0132 (9)	0.0130 (9)	0.0141 (9)	−0.0031 (7)	−0.0002 (7)	−0.0006 (7)
C32	0.0202 (11)	0.0155 (10)	0.0197 (9)	0.0008 (8)	−0.0018 (7)	−0.0009 (7)
C33	0.0232 (11)	0.0251 (11)	0.0205 (10)	−0.0002 (9)	0.0051 (8)	−0.0075 (8)
C34	0.0311 (12)	0.0271 (11)	0.0147 (10)	−0.0100 (10)	0.0034 (8)	−0.0015 (8)
C35	0.0278 (12)	0.0241 (11)	0.0163 (10)	−0.0072 (9)	−0.0061 (8)	0.0047 (8)
C36	0.0155 (10)	0.0195 (10)	0.0183 (9)	−0.0008 (8)	−0.0031 (7)	0.0028 (7)
Br1	0.02371 (12)	0.02182 (11)	0.02270 (11)	−0.00315 (9)	0.00138 (8)	0.00234 (8)
C37	0.0328 (13)	0.0269 (12)	0.0270 (11)	0.0017 (10)	−0.0026 (9)	−0.0020 (9)
C38	0.0340 (13)	0.0179 (10)	0.0133 (9)	−0.0094 (9)	−0.0076 (8)	0.0045 (8)
N2	0.0332 (12)	0.0361 (11)	0.0276 (10)	−0.0023 (10)	−0.0035 (8)	0.0065 (9)

P1—N1	1.5767 (16)	C18—H18	0.9500
P1—C1	1.7942 (19)	C19—C24	1.397 (3)
P1—C13	1.7988 (18)	C19—C20	1.397 (3)
P1—C7	1.7997 (18)	C20—C21	1.389 (3)
N1—P2	1.5797 (15)	C20—H20	0.9500
P2—C31	1.7963 (18)	C21—C22	1.387 (3)
P2—C19	1.7978 (18)	C21—H21	0.9500
P2—C25	1.8063 (19)	C22—C23	1.386 (3)
C1—C2	1.394 (3)	C22—H22	0.9500
C1—C6	1.402 (3)	C23—C24	1.390 (3)
C2—C3	1.384 (3)	C23—H23	0.9500
C2—H2	0.9500	C24—H24	0.9500
C3—C4	1.386 (3)	C25—C30	1.395 (3)
C3—H3	0.9500	C25—C26	1.396 (3)
C4—C5	1.378 (3)	C26—C27	1.385 (3)
C4—H4	0.9500	C26—H26	0.9500
C5—C6	1.381 (3)	C27—C28	1.387 (3)
C5—H5	0.9500	C27—H27	0.9500
C6—H6	0.9500	C28—C29	1.388 (3)
C7—C8	1.395 (3)	C28—H28	0.9500
C7—C12	1.399 (3)	C29—C30	1.391 (3)
C8—C9	1.392 (3)	C29—H29	0.9500
C8—H8	0.9500	C30—H30	0.9500
C9—C10	1.382 (3)	C31—C32	1.396 (3)
C9—H9	0.9500	C31—C36	1.396 (3)
C10—C11	1.381 (3)	C32—C33	1.386 (3)
C10—H10	0.9500	C32—H32	0.9500
C11—C12	1.389 (3)	C33—C34	1.388 (3)
C11—H11	0.9500	C33—H33	0.9500
C12—H12	0.9500	C34—C35	1.383 (3)
C13—C18	1.390 (3)	C34—H34	0.9500
C13—C14	1.397 (3)	C35—C36	1.388 (3)
C14—C15	1.385 (3)	C35—H35	0.9500
C14—H14	0.9500	C36—H36	0.9500
C15—C16	1.388 (3)	C37—C38	1.491 (3)
C15—H15	0.9500	C37—H37A	0.9800
C16—C17	1.381 (3)	C37—H37B	0.9800
C16—H16	0.9500	C37—H37C	0.9800
C17—C18	1.392 (3)	C38—N2	1.092 (3)
C17—H17	0.9500
N1—P1—C1	115.92 (8)	C13—C18—C17	119.83 (18)
N1—P1—C13	108.54 (8)	C13—C18—H18	120.1
C1—P1—C13	107.16 (9)	C17—C18—H18	120.1
N1—P1—C7	109.95 (9)	C24—C19—C20	120.13 (17)
C1—P1—C7	108.14 (9)	C24—C19—P2	120.81 (14)
C13—P1—C7	106.72 (8)	C20—C19—P2	118.88 (14)
P1—N1—P2	142.88 (10)	C21—C20—C19	119.40 (18)
N1—P2—C31	113.51 (8)	C21—C20—H20	120.3
N1—P2—C19	107.22 (8)	C19—C20—H20	120.3
C31—P2—C19	109.03 (8)	C22—C21—C20	120.29 (18)
N1—P2—C25	112.90 (8)	C22—C21—H21	119.9
C31—P2—C25	107.67 (8)	C20—C21—H21	119.9
C19—P2—C25	106.22 (9)	C23—C22—C21	120.52 (19)
C2—C1—C6	119.84 (17)	C23—C22—H22	119.7
C2—C1—P1	119.63 (14)	C21—C22—H22	119.7
C6—C1—P1	120.11 (14)	C22—C23—C24	119.75 (18)
C3—C2—C1	120.03 (19)	C22—C23—H23	120.1
C3—C2—H2	120.0	C24—C23—H23	120.1
C1—C2—H2	120.0	C23—C24—C19	119.90 (18)
C2—C3—C4	119.7 (2)	C23—C24—H24	120.1
C2—C3—H3	120.1	C19—C24—H24	120.1
C4—C3—H3	120.1	C30—C25—C26	119.23 (18)
C5—C4—C3	120.44 (19)	C30—C25—P2	121.42 (14)
C5—C4—H4	119.8	C26—C25—P2	119.35 (14)
C3—C4—H4	119.8	C27—C26—C25	120.30 (18)
C4—C5—C6	120.7 (2)	C27—C26—H26	119.9
C4—C5—H5	119.7	C25—C26—H26	119.9
C6—C5—H5	119.7	C26—C27—C28	120.23 (18)
C5—C6—C1	119.27 (19)	C26—C27—H27	119.9
C5—C6—H6	120.4	C28—C27—H27	119.9
C1—C6—H6	120.4	C27—C28—C29	119.95 (18)
C8—C7—C12	119.63 (17)	C27—C28—H28	120.0
C8—C7—P1	121.62 (15)	C29—C28—H28	120.0
C12—C7—P1	118.57 (14)	C28—C29—C30	120.05 (19)
C9—C8—C7	120.05 (19)	C28—C29—H29	120.0
C9—C8—H8	120.0	C30—C29—H29	120.0
C7—C8—H8	120.0	C29—C30—C25	120.22 (18)
C10—C9—C8	119.7 (2)	C29—C30—H30	119.9
C10—C9—H9	120.1	C25—C30—H30	119.9
C8—C9—H9	120.1	C32—C31—C36	119.58 (17)
C11—C10—C9	120.70 (19)	C32—C31—P2	118.27 (14)
C11—C10—H10	119.6	C36—C31—P2	122.13 (15)
C9—C10—H10	119.6	C33—C32—C31	120.02 (18)
C10—C11—C12	120.1 (2)	C33—C32—H32	120.0
C10—C11—H11	119.9	C31—C32—H32	120.0
C12—C11—H11	119.9	C32—C33—C34	120.1 (2)
C11—C12—C7	119.72 (19)	C32—C33—H33	120.0
C11—C12—H12	120.1	C34—C33—H33	120.0
C7—C12—H12	120.1	C35—C34—C33	120.18 (18)
C18—C13—C14	119.61 (17)	C35—C34—H34	119.9
C18—C13—P1	120.29 (14)	C33—C34—H34	119.9
C14—C13—P1	120.10 (14)	C34—C35—C36	120.16 (19)
C15—C14—C13	120.20 (18)	C34—C35—H35	119.9
C15—C14—H14	119.9	C36—C35—H35	119.9
C13—C14—H14	119.9	C35—C36—C31	119.96 (19)
C14—C15—C16	119.94 (19)	C35—C36—H36	120.0
C14—C15—H15	120.0	C31—C36—H36	120.0
C16—C15—H15	120.0	C38—C37—H37A	109.5
C17—C16—C15	120.11 (19)	C38—C37—H37B	109.5
C17—C16—H16	119.9	H37A—C37—H37B	109.5
C15—C16—H16	119.9	C38—C37—H37C	109.5
C16—C17—C18	120.31 (18)	H37A—C37—H37C	109.5
C16—C17—H17	119.8	H37B—C37—H37C	109.5
C18—C17—H17	119.8	N2—C38—C37	178.4 (2)
C1—P1—N1—P2	−12.2 (2)	C14—C13—C18—C17	0.3 (3)
C13—P1—N1—P2	−132.79 (17)	P1—C13—C18—C17	179.90 (14)
C7—P1—N1—P2	110.82 (18)	C16—C17—C18—C13	−0.8 (3)
P1—N1—P2—C31	35.6 (2)	N1—P2—C19—C24	−158.31 (15)
P1—N1—P2—C19	156.03 (17)	C31—P2—C19—C24	−35.04 (18)
P1—N1—P2—C25	−87.33 (19)	C25—P2—C19—C24	80.74 (16)
N1—P1—C1—C2	77.13 (17)	N1—P2—C19—C20	26.59 (17)
C13—P1—C1—C2	−161.53 (15)	C31—P2—C19—C20	149.86 (15)
C7—P1—C1—C2	−46.83 (17)	C25—P2—C19—C20	−94.37 (16)
N1—P1—C1—C6	−95.43 (17)	C24—C19—C20—C21	−0.4 (3)
C13—P1—C1—C6	25.91 (18)	P2—C19—C20—C21	174.72 (14)
C7—P1—C1—C6	140.62 (15)	C19—C20—C21—C22	−0.4 (3)
C6—C1—C2—C3	1.0 (3)	C20—C21—C22—C23	1.0 (3)
P1—C1—C2—C3	−171.53 (16)	C21—C22—C23—C24	−0.7 (3)
C1—C2—C3—C4	−1.8 (3)	C22—C23—C24—C19	−0.1 (3)
C2—C3—C4—C5	0.6 (3)	C20—C19—C24—C23	0.7 (3)
C3—C4—C5—C6	1.5 (3)	P2—C19—C24—C23	−174.36 (15)
C4—C5—C6—C1	−2.2 (3)	N1—P2—C25—C30	−116.56 (16)
C2—C1—C6—C5	0.9 (3)	C31—P2—C25—C30	117.35 (16)
P1—C1—C6—C5	173.48 (16)	C19—P2—C25—C30	0.67 (17)
N1—P1—C7—C8	−164.10 (15)	N1—P2—C25—C26	62.58 (17)
C1—P1—C7—C8	−36.63 (18)	C31—P2—C25—C26	−63.51 (17)
C13—P1—C7—C8	78.37 (17)	C19—P2—C25—C26	179.81 (15)
N1—P1—C7—C12	20.69 (17)	C30—C25—C26—C27	1.5 (3)
C1—P1—C7—C12	148.16 (15)	P2—C25—C26—C27	−177.65 (15)
C13—P1—C7—C12	−96.84 (16)	C25—C26—C27—C28	−0.1 (3)
C12—C7—C8—C9	0.9 (3)	C26—C27—C28—C29	−1.3 (3)
P1—C7—C8—C9	−174.29 (15)	C27—C28—C29—C30	1.4 (3)
C7—C8—C9—C10	0.7 (3)	C28—C29—C30—C25	0.0 (3)
C8—C9—C10—C11	−2.1 (3)	C26—C25—C30—C29	−1.5 (3)
C9—C10—C11—C12	1.9 (3)	P2—C25—C30—C29	177.68 (14)
C10—C11—C12—C7	−0.3 (3)	N1—P2—C31—C32	44.97 (17)
C8—C7—C12—C11	−1.1 (3)	C19—P2—C31—C32	−74.47 (16)
P1—C7—C12—C11	174.25 (15)	C25—P2—C31—C32	170.70 (14)
N1—P1—C13—C18	2.28 (17)	N1—P2—C31—C36	−133.64 (16)
C1—P1—C13—C18	−123.61 (15)	C19—P2—C31—C36	106.93 (16)
C7—P1—C13—C18	120.73 (15)	C25—P2—C31—C36	−7.91 (18)
N1—P1—C13—C14	−178.09 (14)	C36—C31—C32—C33	0.1 (3)
C1—P1—C13—C14	56.02 (17)	P2—C31—C32—C33	−178.58 (15)
C7—P1—C13—C14	−59.64 (17)	C31—C32—C33—C34	−0.5 (3)
C18—C13—C14—C15	0.2 (3)	C32—C33—C34—C35	0.2 (3)
P1—C13—C14—C15	−179.39 (14)	C33—C34—C35—C36	0.4 (3)
C13—C14—C15—C16	−0.2 (3)	C34—C35—C36—C31	−0.8 (3)
C14—C15—C16—C17	−0.4 (3)	C32—C31—C36—C35	0.6 (3)
C15—C16—C17—C18	0.9 (3)	P2—C31—C36—C35	179.15 (15)

P1—N1	1.5767 (16)
P1—C1	1.7942 (19)
P1—C13	1.7988 (18)
P1—C7	1.7997 (18)
P2—N1	1.5797 (15)
P2—C31	1.7963 (18)
P2—C19	1.7978 (18)
P2—C25	1.8063 (19)

P1—N1—P2

142.88 (10)