[3-(Iodo-acetamido)prop-yl]triphenyl-phospho-nium tetra-phenyl-borate.

The title compound, C(23)H(24)INOP(+)·C(24)H(20)B(-), was prepared by treatment of 3-amino-propyl triphenyl-phospho-nium bromide hydrogen bromide with p-nitro-phenyl iodo-acetate at 203 K. The asymmetric unit contains a single cation and anion, which are linked in the crystal by inter-molecular N-H⋯π and inversion-related R(2) (2)(14) C-H⋯O inter-actions, which combine to form chains of cations and anions along the c axis.

Related literature

For the development and applications of mitochondrially targeted bio-active compounds, see Murphy & Smith (2007 ▶); Porteous et al. (2010 ▶). For the use of iodo­acetamides in labelling cysteine residues, see Baty et al. (2002 ▶); Kim et al. (2000 ▶); Ying et al. (2007 ▶). For the synthesis of amino­alkyl triphenyl­phospho­nium salts, see McAllister et al. (1980 ▶). For the synthesis of iodo­acetamides, see Trujillo et al. (1991 ▶). For related structures see Czerwinski (1986 ▶); Dubourg et al. (1986 ▶); Kerrigan et al.(1996 ▶); Lo et al.(2002 ▶). For a review of hydrogen bonding networks, see Bernstein et al.(1995 ▶).

Experimental

Crystal data

C23H24INOP+·C24H20B−

M = 807.51

Monoclinic,

a = 14.552 (3) Å

b = 12.108 (2) Å

c = 21.966 (4) Å

β = 99.49 (3)°

V = 3817.3 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.92 mm−1

T = 89 K

0.22 × 0.20 × 0.2 0mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2006 ▶) T min = 0.661, T max = 0.832

38267 measured reflections

9958 independent reflections

7291 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.103

S = 1.11

9958 reflections

469 parameters

H-atom parameters constrained

Δρmax = 0.74 e Å−3

Δρmin = −0.99 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: APEX2 and SAINT (Bruker, 2006 ▶); data reduction: SAINT (Bruker, 2006 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶), enCIFer (Allen et al., 2004 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681000142X/nc2174sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681000142X/nc2174Isup2.hkl

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

C23H24INOP+·C24H20B−	F(000) = 1656
Mr = 807.51	Dx = 1.405 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6317 reflections
a = 14.552 (3) Å	θ = 2.5–28.7°
b = 12.108 (2) Å	µ = 0.92 mm−1
c = 21.966 (4) Å	T = 89 K
β = 99.49 (3)°	Prism, colourless
V = 3817.3 (13) Å3	0.22 × 0.2 × 0.2 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	9958 independent reflections
Radiation source: fine-focus sealed tube	7291 reflections with I > 2σ(I)
graphite	Rint = 0.049
φ and ω scans	θmax = 29.1°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −13→19
Tmin = 0.661, Tmax = 0.832	k = −16→16
38267 measured reflections	l = −29→29

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.0467P)2] where P = (Fo2 + 2Fc2)/3
9958 reflections	(Δ/σ)max = 0.002
469 parameters	Δρmax = 0.74 e Å−3
0 restraints	Δρmin = −0.99 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
C1	0.64225 (17)	0.08981 (19)	0.51219 (11)	0.0171 (5)
H1A	0.6231	0.158	0.5297	0.02*
H1B	0.5865	0.0549	0.4902	0.02*
C2	0.68361 (17)	0.01362 (19)	0.56566 (11)	0.0182 (5)
H2A	0.6959	−0.0584	0.5494	0.022*
H2B	0.7424	0.0439	0.5861	0.022*
C3	0.61750 (18)	0.00073 (19)	0.61254 (11)	0.0204 (5)
H3A	0.5628	−0.0399	0.5936	0.025*
H3B	0.6482	−0.0423	0.6473	0.025*
C4	0.51294 (18)	0.1611 (2)	0.60641 (11)	0.0204 (5)
C5	0.49861 (18)	0.2755 (2)	0.63068 (12)	0.0240 (6)
H5A	0.521	0.2783	0.6748	0.029*
H5B	0.4328	0.2937	0.6235	0.029*
C11	0.73474 (16)	0.00477 (19)	0.41211 (11)	0.0160 (5)
C12	0.78439 (18)	−0.08572 (19)	0.44061 (12)	0.0203 (5)
H12	0.8178	−0.0792	0.4804	0.024*
C13	0.78336 (18)	−0.1849 (2)	0.40913 (13)	0.0262 (6)
H13	0.815	−0.2457	0.4281	0.031*
C14	0.73523 (18)	−0.1936 (2)	0.34938 (13)	0.0269 (6)
H14	0.7342	−0.2608	0.3287	0.032*
C15	0.6888 (2)	−0.1039 (2)	0.32005 (13)	0.0258 (6)
H15	0.6585	−0.1098	0.2795	0.031*
C16	0.68773 (18)	−0.0041 (2)	0.35196 (11)	0.0204 (5)
H16	0.6555	0.0563	0.3329	0.024*
C21	0.65711 (17)	0.22816 (18)	0.40569 (10)	0.0166 (5)
C22	0.56359 (17)	0.25297 (19)	0.40603 (11)	0.0178 (5)
H22	0.5315	0.2179	0.4338	0.021*
C23	0.51862 (18)	0.3302 (2)	0.36477 (12)	0.0221 (6)
H23	0.4562	0.3466	0.3648	0.026*
C24	0.5667 (2)	0.3832 (2)	0.32344 (12)	0.0239 (6)
H24	0.5361	0.4344	0.2957	0.029*
C25	0.6600 (2)	0.3600 (2)	0.32343 (12)	0.0259 (6)
H25	0.6921	0.3962	0.296	0.031*
C26	0.70566 (18)	0.2824 (2)	0.36446 (11)	0.0221 (6)
H26	0.7682	0.2667	0.3645	0.027*
C31	0.82434 (17)	0.18234 (19)	0.49480 (10)	0.0153 (5)
C32	0.90545 (17)	0.1740 (2)	0.46827 (11)	0.0187 (5)
H32	0.906	0.1311	0.4332	0.022*
C33	0.98484 (18)	0.2306 (2)	0.49516 (11)	0.0224 (6)
H33	1.0388	0.227	0.4777	0.027*
C34	0.98368 (18)	0.2925 (2)	0.54801 (12)	0.0221 (6)
H34	1.0372	0.33	0.5658	0.027*
C35	0.90392 (17)	0.29959 (19)	0.57498 (11)	0.0189 (5)
H35	0.9045	0.3408	0.6108	0.023*
C36	0.82383 (18)	0.24521 (18)	0.54849 (10)	0.0167 (5)
H36	0.77	0.2502	0.566	0.02*
N1	0.58821 (15)	0.10650 (16)	0.63510 (9)	0.0203 (5)
H1	0.6202	0.1347	0.6678	0.024*
O1	0.46005 (13)	0.12292 (14)	0.56173 (8)	0.0247 (4)
P1	0.71663 (4)	0.12487 (5)	0.45667 (3)	0.01393 (14)
I1	0.574759 (12)	0.392989 (13)	0.583303 (8)	0.02472 (7)
C41	0.96560 (17)	0.56909 (19)	0.67978 (10)	0.0158 (5)
C42	0.95432 (17)	0.48566 (19)	0.72216 (10)	0.0158 (5)
H42	0.9033	0.4891	0.7426	0.019*
C43	1.01627 (18)	0.39780 (19)	0.73499 (11)	0.0189 (5)
H43	1.0056	0.3439	0.7632	0.023*
C44	1.09355 (19)	0.3903 (2)	0.70599 (12)	0.0217 (6)
H44	1.1347	0.3314	0.7143	0.026*
C45	1.10912 (18)	0.4726 (2)	0.66406 (11)	0.0215 (6)
H45	1.1613	0.4696	0.6447	0.026*
C46	1.04555 (17)	0.5590 (2)	0.65170 (11)	0.0177 (5)
H46	1.0564	0.6128	0.6235	0.021*
C51	0.82725 (17)	0.64150 (19)	0.59114 (11)	0.0161 (5)
C52	0.85473 (18)	0.5664 (2)	0.54902 (11)	0.0189 (5)
H52	0.9147	0.5374	0.5572	0.023*
C53	0.7963 (2)	0.5332 (2)	0.49554 (12)	0.0258 (6)
H53	0.817	0.4818	0.4694	0.031*
C54	0.7073 (2)	0.5763 (2)	0.48112 (12)	0.0265 (6)
H54	0.6676	0.5533	0.4458	0.032*
C55	0.67821 (19)	0.6545 (2)	0.52008 (12)	0.0269 (6)
H55	0.6193	0.6858	0.5103	0.032*
C56	0.73713 (18)	0.6860 (2)	0.57372 (11)	0.0220 (6)
H56	0.7163	0.7386	0.5991	0.026*
C61	0.81277 (16)	0.67687 (19)	0.70793 (10)	0.0153 (5)
C62	0.74884 (17)	0.58898 (19)	0.71142 (11)	0.0176 (5)
H62	0.7519	0.5276	0.6864	0.021*
C63	0.68308 (18)	0.58957 (19)	0.74946 (11)	0.0190 (5)
H63	0.6448	0.5284	0.7507	0.023*
C64	0.67309 (18)	0.6812 (2)	0.78639 (11)	0.0199 (5)
H64	0.6281	0.6823	0.8119	0.024*
C65	0.73185 (17)	0.7703 (2)	0.78403 (11)	0.0195 (5)
H65	0.7258	0.8328	0.8077	0.023*
C66	0.80049 (17)	0.76719 (19)	0.74611 (11)	0.0177 (5)
H66	0.8398	0.8278	0.7462	0.021*
C71	0.94558 (16)	0.78910 (19)	0.66057 (10)	0.0152 (5)
C72	1.03056 (18)	0.8086 (2)	0.69976 (11)	0.0200 (5)
H72	1.0565	0.7519	0.7256	0.024*
C73	1.07757 (19)	0.9091 (2)	0.70155 (12)	0.0233 (6)
H73	1.1342	0.9178	0.7277	0.028*
C74	1.04013 (19)	0.9965 (2)	0.66442 (11)	0.0220 (6)
H74	1.071	1.0639	0.6656	0.026*
C75	0.95639 (18)	0.9812 (2)	0.62579 (11)	0.0214 (5)
H75	0.9306	1.0386	0.6005	0.026*
C76	0.91000 (18)	0.87998 (18)	0.62445 (11)	0.0179 (5)
H76	0.853	0.8724	0.5985	0.021*
B1	0.8892 (2)	0.6704 (2)	0.66017 (12)	0.0159 (6)

	U11	U22	U33	U12	U13	U23
C1	0.0157 (12)	0.0186 (13)	0.0157 (12)	−0.0002 (9)	−0.0007 (10)	−0.0002 (9)
C2	0.0203 (13)	0.0175 (12)	0.0160 (12)	−0.0005 (10)	0.0004 (10)	0.0020 (10)
C3	0.0259 (14)	0.0173 (13)	0.0174 (12)	−0.0036 (10)	0.0016 (11)	0.0040 (10)
C4	0.0197 (13)	0.0252 (14)	0.0178 (12)	−0.0049 (10)	0.0078 (11)	−0.0010 (11)
C5	0.0222 (14)	0.0271 (14)	0.0238 (14)	0.0007 (11)	0.0069 (11)	−0.0051 (11)
C11	0.0156 (12)	0.0179 (12)	0.0149 (11)	−0.0014 (9)	0.0038 (10)	−0.0006 (9)
C12	0.0192 (13)	0.0203 (13)	0.0202 (13)	0.0029 (10)	−0.0006 (11)	0.0004 (10)
C13	0.0201 (14)	0.0210 (14)	0.0378 (16)	0.0034 (10)	0.0055 (12)	0.0010 (12)
C14	0.0235 (14)	0.0225 (14)	0.0372 (16)	−0.0044 (11)	0.0125 (13)	−0.0142 (12)
C15	0.0246 (15)	0.0299 (15)	0.0218 (14)	−0.0054 (11)	0.0006 (12)	−0.0099 (11)
C16	0.0211 (13)	0.0207 (13)	0.0182 (12)	−0.0026 (10)	−0.0004 (11)	−0.0011 (10)
C21	0.0187 (13)	0.0134 (12)	0.0158 (12)	−0.0001 (9)	−0.0027 (10)	−0.0008 (9)
C22	0.0204 (13)	0.0149 (12)	0.0170 (12)	−0.0002 (9)	−0.0001 (10)	−0.0002 (10)
C23	0.0183 (13)	0.0213 (14)	0.0241 (13)	0.0047 (10)	−0.0035 (11)	−0.0001 (11)
C24	0.0295 (15)	0.0178 (13)	0.0223 (14)	0.0035 (10)	−0.0014 (12)	0.0050 (10)
C25	0.0284 (15)	0.0243 (14)	0.0246 (14)	−0.0009 (11)	0.0031 (12)	0.0097 (11)
C26	0.0187 (13)	0.0259 (14)	0.0215 (13)	0.0001 (11)	0.0026 (11)	0.0054 (11)
C31	0.0172 (12)	0.0144 (12)	0.0129 (11)	0.0015 (9)	−0.0019 (10)	0.0008 (9)
C32	0.0196 (13)	0.0219 (13)	0.0139 (12)	0.0003 (10)	0.0007 (10)	−0.0034 (10)
C33	0.0170 (13)	0.0292 (15)	0.0208 (13)	−0.0016 (11)	0.0022 (11)	−0.0036 (11)
C34	0.0192 (13)	0.0223 (13)	0.0229 (13)	−0.0034 (10)	−0.0026 (11)	−0.0032 (11)
C35	0.0256 (14)	0.0168 (13)	0.0134 (12)	−0.0015 (10)	0.0005 (11)	−0.0028 (9)
C36	0.0211 (13)	0.0142 (12)	0.0146 (11)	0.0015 (9)	0.0021 (10)	0.0001 (9)
N1	0.0238 (12)	0.0224 (11)	0.0138 (10)	−0.0016 (9)	0.0007 (9)	−0.0022 (8)
O1	0.0191 (10)	0.0288 (10)	0.0253 (10)	−0.0038 (7)	0.0005 (8)	−0.0048 (8)
P1	0.0146 (3)	0.0143 (3)	0.0118 (3)	0.0008 (2)	−0.0009 (2)	0.0000 (2)
I1	0.02367 (10)	0.01857 (10)	0.03027 (11)	0.00050 (7)	−0.00038 (8)	−0.00280 (7)
C41	0.0184 (12)	0.0158 (12)	0.0110 (11)	−0.0013 (9)	−0.0041 (10)	−0.0040 (9)
C42	0.0163 (12)	0.0184 (12)	0.0120 (11)	0.0009 (9)	0.0001 (10)	−0.0028 (9)
C43	0.0236 (14)	0.0172 (13)	0.0150 (12)	0.0009 (10)	0.0007 (11)	0.0006 (10)
C44	0.0246 (14)	0.0191 (13)	0.0188 (13)	0.0078 (10)	−0.0042 (11)	−0.0028 (10)
C45	0.0177 (13)	0.0284 (14)	0.0176 (12)	0.0043 (11)	0.0007 (11)	−0.0063 (11)
C46	0.0197 (13)	0.0193 (12)	0.0133 (12)	0.0004 (10)	0.0000 (10)	0.0003 (10)
C51	0.0213 (13)	0.0109 (11)	0.0158 (12)	−0.0017 (9)	0.0019 (10)	0.0024 (9)
C52	0.0200 (13)	0.0173 (12)	0.0187 (13)	0.0000 (10)	0.0014 (11)	0.0025 (10)
C53	0.0397 (17)	0.0193 (14)	0.0163 (13)	−0.0018 (11)	−0.0014 (12)	−0.0023 (10)
C54	0.0310 (16)	0.0281 (15)	0.0166 (13)	−0.0054 (12)	−0.0074 (12)	0.0011 (11)
C55	0.0217 (14)	0.0336 (16)	0.0223 (14)	0.0021 (12)	−0.0057 (12)	0.0061 (12)
C56	0.0248 (14)	0.0206 (13)	0.0192 (13)	0.0013 (10)	−0.0004 (11)	0.0005 (10)
C61	0.0144 (12)	0.0152 (12)	0.0146 (11)	0.0036 (9)	−0.0028 (10)	0.0021 (9)
C62	0.0177 (12)	0.0133 (12)	0.0199 (13)	0.0025 (9)	−0.0027 (10)	−0.0013 (9)
C63	0.0192 (13)	0.0152 (13)	0.0220 (13)	0.0022 (9)	0.0014 (11)	0.0013 (10)
C64	0.0183 (13)	0.0242 (14)	0.0172 (12)	0.0032 (10)	0.0031 (10)	0.0036 (10)
C65	0.0260 (14)	0.0156 (13)	0.0168 (12)	0.0031 (10)	0.0029 (11)	−0.0036 (10)
C66	0.0186 (13)	0.0150 (12)	0.0182 (12)	−0.0014 (9)	−0.0008 (10)	0.0012 (10)
C71	0.0178 (12)	0.0159 (12)	0.0119 (11)	0.0013 (9)	0.0028 (10)	−0.0020 (9)
C72	0.0237 (14)	0.0184 (13)	0.0161 (12)	−0.0002 (10)	−0.0019 (11)	−0.0006 (10)
C73	0.0238 (14)	0.0235 (14)	0.0213 (14)	−0.0034 (10)	0.0003 (12)	−0.0073 (11)
C74	0.0285 (15)	0.0153 (13)	0.0243 (14)	−0.0033 (10)	0.0103 (12)	−0.0033 (10)
C75	0.0278 (15)	0.0164 (13)	0.0204 (13)	0.0044 (10)	0.0051 (11)	0.0044 (10)
C76	0.0176 (13)	0.0172 (13)	0.0185 (12)	0.0040 (9)	0.0018 (10)	−0.0002 (10)
B1	0.0187 (14)	0.0131 (13)	0.0141 (13)	0.0007 (10)	−0.0027 (11)	0.0010 (10)

C1—C2	1.536 (3)	C36—H36	0.93
C1—P1	1.810 (3)	N1—H1	0.86
C1—H1A	0.97	C41—C42	1.402 (3)
C1—H1B	0.97	C41—C46	1.409 (3)
C2—C3	1.529 (3)	C41—B1	1.664 (4)
C2—H2A	0.97	C42—C43	1.393 (3)
C2—H2B	0.97	C42—H42	0.93
C3—N1	1.462 (3)	C43—C44	1.384 (4)
C3—H3A	0.97	C43—H43	0.93
C3—H3B	0.97	C44—C45	1.400 (4)
C4—O1	1.233 (3)	C44—H44	0.93
C4—N1	1.344 (3)	C45—C46	1.394 (3)
C4—C5	1.511 (3)	C45—H45	0.93
C5—I1	2.172 (3)	C46—H46	0.93
C5—H5A	0.97	C51—C52	1.402 (4)
C5—H5B	0.97	C51—C56	1.411 (3)
C11—C16	1.388 (3)	C51—B1	1.668 (3)
C11—C12	1.402 (3)	C52—C53	1.391 (3)
C11—P1	1.796 (2)	C52—H52	0.93
C12—C13	1.384 (3)	C53—C54	1.383 (4)
C12—H12	0.93	C53—H53	0.93
C13—C14	1.386 (4)	C54—C55	1.389 (4)
C13—H13	0.93	C54—H54	0.93
C14—C15	1.382 (4)	C55—C56	1.391 (3)
C14—H14	0.93	C55—H55	0.93
C15—C16	1.398 (3)	C56—H56	0.93
C15—H15	0.93	C61—C66	1.407 (3)
C16—H16	0.93	C61—C62	1.424 (3)
C21—C22	1.395 (3)	C61—B1	1.652 (4)
C21—C26	1.401 (3)	C62—C63	1.370 (4)
C21—P1	1.802 (2)	C62—H62	0.93
C22—C23	1.389 (3)	C63—C64	1.396 (3)
C22—H22	0.93	C63—H63	0.93
C23—C24	1.391 (4)	C64—C65	1.383 (3)
C23—H23	0.93	C64—H64	0.93
C24—C25	1.387 (4)	C65—C66	1.403 (3)
C24—H24	0.93	C65—H65	0.93
C25—C26	1.392 (3)	C66—H66	0.93
C25—H25	0.93	C71—C76	1.405 (3)
C26—H26	0.93	C71—C72	1.405 (3)
C31—C32	1.404 (3)	C71—B1	1.654 (4)
C31—C36	1.405 (3)	C72—C73	1.394 (3)
C31—P1	1.791 (2)	C72—H72	0.93
C32—C33	1.389 (3)	C73—C74	1.391 (4)
C32—H32	0.93	C73—H73	0.93
C33—C34	1.384 (3)	C74—C75	1.378 (4)
C33—H33	0.93	C74—H74	0.93
C34—C35	1.390 (4)	C75—C76	1.397 (3)
C34—H34	0.93	C75—H75	0.93
C35—C36	1.381 (3)	C76—H76	0.93
C35—H35	0.93
C2—C1—P1	116.98 (17)	C31—P1—C11	111.93 (11)
C2—C1—H1A	108.1	C31—P1—C21	108.34 (11)
P1—C1—H1A	108.1	C11—P1—C21	108.77 (11)
C2—C1—H1B	108.1	C31—P1—C1	110.52 (11)
P1—C1—H1B	108.1	C11—P1—C1	109.58 (11)
H1A—C1—H1B	107.3	C21—P1—C1	107.58 (11)
C3—C2—C1	111.4 (2)	C42—C41—C46	115.1 (2)
C3—C2—H2A	109.3	C42—C41—B1	123.8 (2)
C1—C2—H2A	109.3	C46—C41—B1	121.0 (2)
C3—C2—H2B	109.3	C43—C42—C41	122.8 (2)
C1—C2—H2B	109.3	C43—C42—H42	118.6
H2A—C2—H2B	108	C41—C42—H42	118.6
N1—C3—C2	112.95 (19)	C44—C43—C42	120.3 (2)
N1—C3—H3A	109	C44—C43—H43	119.8
C2—C3—H3A	109	C42—C43—H43	119.8
N1—C3—H3B	109	C43—C44—C45	119.2 (2)
C2—C3—H3B	109	C43—C44—H44	120.4
H3A—C3—H3B	107.8	C45—C44—H44	120.4
O1—C4—N1	122.9 (2)	C46—C45—C44	119.2 (2)
O1—C4—C5	121.3 (2)	C46—C45—H45	120.4
N1—C4—C5	115.8 (2)	C44—C45—H45	120.4
C4—C5—I1	108.70 (16)	C45—C46—C41	123.3 (2)
C4—C5—H5A	110	C45—C46—H46	118.3
I1—C5—H5A	110	C41—C46—H46	118.3
C4—C5—H5B	110	C52—C51—C56	115.0 (2)
I1—C5—H5B	110	C52—C51—B1	124.5 (2)
H5A—C5—H5B	108.3	C56—C51—B1	120.3 (2)
C16—C11—C12	120.1 (2)	C53—C52—C51	122.9 (2)
C16—C11—P1	119.20 (19)	C53—C52—H52	118.5
C12—C11—P1	120.03 (18)	C51—C52—H52	118.5
C13—C12—C11	119.5 (2)	C54—C53—C52	120.2 (2)
C13—C12—H12	120.2	C54—C53—H53	119.9
C11—C12—H12	120.2	C52—C53—H53	119.9
C12—C13—C14	120.1 (2)	C53—C54—C55	119.1 (2)
C12—C13—H13	120	C53—C54—H54	120.5
C14—C13—H13	120	C55—C54—H54	120.5
C15—C14—C13	120.9 (2)	C54—C55—C56	120.1 (3)
C15—C14—H14	119.5	C54—C55—H55	120
C13—C14—H14	119.5	C56—C55—H55	120
C14—C15—C16	119.4 (2)	C55—C56—C51	122.7 (2)
C14—C15—H15	120.3	C55—C56—H56	118.7
C16—C15—H15	120.3	C51—C56—H56	118.7
C11—C16—C15	120.0 (2)	C66—C61—C62	113.6 (2)
C11—C16—H16	120	C66—C61—B1	125.5 (2)
C15—C16—H16	120	C62—C61—B1	120.9 (2)
C22—C21—C26	119.9 (2)	C63—C62—C61	123.9 (2)
C22—C21—P1	121.02 (18)	C63—C62—H62	118.1
C26—C21—P1	119.03 (19)	C61—C62—H62	118.1
C23—C22—C21	119.8 (2)	C62—C63—C64	120.6 (2)
C23—C22—H22	120.1	C62—C63—H63	119.7
C21—C22—H22	120.1	C64—C63—H63	119.7
C22—C23—C24	120.2 (2)	C65—C64—C63	118.3 (2)
C22—C23—H23	119.9	C65—C64—H64	120.9
C24—C23—H23	119.9	C63—C64—H64	120.9
C25—C24—C23	120.3 (2)	C64—C65—C66	120.4 (2)
C25—C24—H24	119.8	C64—C65—H65	119.8
C23—C24—H24	119.8	C66—C65—H65	119.8
C24—C25—C26	119.9 (3)	C65—C66—C61	123.2 (2)
C24—C25—H25	120	C65—C66—H66	118.4
C26—C25—H25	120	C61—C66—H66	118.4
C25—C26—C21	119.8 (2)	C76—C71—C72	114.8 (2)
C25—C26—H26	120.1	C76—C71—B1	122.8 (2)
C21—C26—H26	120.1	C72—C71—B1	122.3 (2)
C32—C31—C36	120.6 (2)	C73—C72—C71	122.8 (2)
C32—C31—P1	120.57 (18)	C73—C72—H72	118.6
C36—C31—P1	118.53 (19)	C71—C72—H72	118.6
C33—C32—C31	119.0 (2)	C74—C73—C72	120.3 (2)
C33—C32—H32	120.5	C74—C73—H73	119.8
C31—C32—H32	120.5	C72—C73—H73	119.8
C34—C33—C32	120.0 (3)	C75—C74—C73	118.7 (2)
C34—C33—H33	120	C75—C74—H74	120.7
C32—C33—H33	120	C73—C74—H74	120.7
C33—C34—C35	121.1 (2)	C74—C75—C76	120.4 (2)
C33—C34—H34	119.4	C74—C75—H75	119.8
C35—C34—H34	119.4	C76—C75—H75	119.8
C36—C35—C34	119.8 (2)	C75—C76—C71	122.9 (2)
C36—C35—H35	120.1	C75—C76—H76	118.5
C34—C35—H35	120.1	C71—C76—H76	118.5
C35—C36—C31	119.4 (2)	C61—B1—C71	109.94 (19)
C35—C36—H36	120.3	C61—B1—C41	111.19 (19)
C31—C36—H36	120.3	C71—B1—C41	109.2 (2)
C4—N1—C3	122.2 (2)	C61—B1—C51	105.54 (19)
C4—N1—H1	118.9	C71—B1—C51	112.36 (19)
C3—N1—H1	118.9	C41—B1—C51	108.55 (19)
P1—C1—C2—C3	173.97 (16)	C41—C42—C43—C44	0.6 (4)
C1—C2—C3—N1	−53.6 (3)	C42—C43—C44—C45	0.6 (4)
O1—C4—C5—I1	−89.9 (3)	C43—C44—C45—C46	−1.1 (4)
N1—C4—C5—I1	87.8 (2)	C44—C45—C46—C41	0.5 (4)
C16—C11—C12—C13	−2.3 (4)	C42—C41—C46—C45	0.6 (3)
P1—C11—C12—C13	168.1 (2)	B1—C41—C46—C45	−176.5 (2)
C11—C12—C13—C14	1.4 (4)	C56—C51—C52—C53	−3.3 (4)
C12—C13—C14—C15	0.8 (4)	B1—C51—C52—C53	171.2 (2)
C13—C14—C15—C16	−2.2 (4)	C51—C52—C53—C54	1.5 (4)
C12—C11—C16—C15	0.9 (4)	C52—C53—C54—C55	1.2 (4)
P1—C11—C16—C15	−169.6 (2)	C53—C54—C55—C56	−1.9 (4)
C14—C15—C16—C11	1.4 (4)	C54—C55—C56—C51	−0.1 (4)
C26—C21—C22—C23	1.0 (3)	C52—C51—C56—C55	2.6 (4)
P1—C21—C22—C23	−177.79 (18)	B1—C51—C56—C55	−172.1 (2)
C21—C22—C23—C24	−0.4 (4)	C66—C61—C62—C63	−1.9 (3)
C22—C23—C24—C25	−0.5 (4)	B1—C61—C62—C63	−179.2 (2)
C23—C24—C25—C26	0.7 (4)	C61—C62—C63—C64	2.3 (4)
C24—C25—C26—C21	0.0 (4)	C62—C63—C64—C65	−0.7 (4)
C22—C21—C26—C25	−0.8 (4)	C63—C64—C65—C66	−1.0 (4)
P1—C21—C26—C25	178.01 (19)	C64—C65—C66—C61	1.4 (4)
C36—C31—C32—C33	−1.3 (3)	C62—C61—C66—C65	0.0 (3)
P1—C31—C32—C33	172.33 (19)	B1—C61—C66—C65	177.3 (2)
C31—C32—C33—C34	1.2 (4)	C76—C71—C72—C73	−1.8 (4)
C32—C33—C34—C35	−0.2 (4)	B1—C71—C72—C73	−178.4 (2)
C33—C34—C35—C36	−0.8 (4)	C71—C72—C73—C74	1.2 (4)
C34—C35—C36—C31	0.7 (3)	C72—C73—C74—C75	−0.4 (4)
C32—C31—C36—C35	0.4 (3)	C73—C74—C75—C76	0.4 (4)
P1—C31—C36—C35	−173.39 (17)	C74—C75—C76—C71	−1.2 (4)
O1—C4—N1—C3	4.9 (4)	C72—C71—C76—C75	1.8 (4)
C5—C4—N1—C3	−172.7 (2)	B1—C71—C76—C75	178.4 (2)
C2—C3—N1—C4	88.6 (3)	C66—C61—B1—C71	−3.3 (3)
C32—C31—P1—C11	31.1 (2)	C62—C61—B1—C71	173.7 (2)
C36—C31—P1—C11	−155.11 (18)	C66—C61—B1—C41	117.8 (2)
C32—C31—P1—C21	−88.8 (2)	C62—C61—B1—C41	−65.2 (3)
C36—C31—P1—C21	85.0 (2)	C66—C61—B1—C51	−124.7 (2)
C32—C31—P1—C1	153.57 (19)	C62—C61—B1—C51	52.3 (3)
C36—C31—P1—C1	−32.7 (2)	C76—C71—B1—C61	−83.7 (3)
C16—C11—P1—C31	−132.7 (2)	C72—C71—B1—C61	92.7 (3)
C12—C11—P1—C31	56.9 (2)	C76—C71—B1—C41	154.0 (2)
C16—C11—P1—C21	−13.0 (2)	C72—C71—B1—C41	−29.6 (3)
C12—C11—P1—C21	176.6 (2)	C76—C71—B1—C51	33.5 (3)
C16—C11—P1—C1	104.4 (2)	C72—C71—B1—C51	−150.1 (2)
C12—C11—P1—C1	−66.1 (2)	C42—C41—B1—C61	13.2 (3)
C22—C21—P1—C31	−130.73 (19)	C46—C41—B1—C61	−169.9 (2)
C26—C21—P1—C31	50.4 (2)	C42—C41—B1—C71	134.7 (2)
C22—C21—P1—C11	107.4 (2)	C46—C41—B1—C71	−48.4 (3)
C26—C21—P1—C11	−71.4 (2)	C42—C41—B1—C51	−102.5 (2)
C22—C21—P1—C1	−11.2 (2)	C46—C41—B1—C51	74.4 (3)
C26—C21—P1—C1	169.94 (19)	C52—C51—B1—C61	−138.3 (2)
C2—C1—P1—C31	−54.4 (2)	C56—C51—B1—C61	35.9 (3)
C2—C1—P1—C11	69.4 (2)	C52—C51—B1—C71	101.9 (3)
C2—C1—P1—C21	−172.53 (17)	C56—C51—B1—C71	−83.9 (3)
C46—C41—C42—C43	−1.2 (3)	C52—C51—B1—C41	−19.1 (3)
B1—C41—C42—C43	175.9 (2)	C56—C51—B1—C41	155.2 (2)

CT01 is the centroid of the C61—C66 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···CT01i	0.86	2.56	3.382 (2)	160
C1—H1B···O1ii	0.97	2.48	3.270 (3)	139

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C61—C66 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯Cgi	0.86	2.56	3.382 (2)	160
C1—H1B⋯O1ii	0.97	2.48	3.270 (3)	139

Symmetry codes: (i) ; (ii) .