A P,O,P'-tridentate mixed-donor scorpionate ligand: 6-[4,6-bis-(diphenyl-phosphino)-10H-phenoxazin-10-yl]hexan-1-ol.

The title compound, C(42)H(39)NO(2)P(2), is a P,O,P'-tridentate scorpionate-type ligand and has one mol-ecule in the asymmetric unit. The angles involving the P atoms range from 100.21 (7) to 104.89 (7)°. The N-hexa-nol group was found to be disordered and was refined over two positions with final occupancies of 0.683 (3) and 0.317 (3) which affected the C-O and C-N bond lengths. The bond lengths for C-O range from 1.402 (2) to 1.415 (2) Å and for C-N from 1.410 (2) to 1.448 (3) Å for the major disorder component; the corresponding ranges for the minor disorder component are 1.429 (3)-1.408 (3) and 1.474 (3)-1.474 (4) Å.

Related literature

For scorpionate type ligands based on the nixantphos backbone, see: Marimuthu et al. (2008a ▶,b ▶). For scorpionate ligands, see: Pettinari, (2004 ▶); Trofimenko (1993 ▶); Leung, (2007 ▶); Mayer et al. (1994 ▶). For hydrogen bonding, see: Chen & Craven (1995 ▶); Monge et al. (1978 ▶). For details of the synthesis, see: Reymond et al. (1996 ▶); Van der Veen et al. (2000 ▶). For a related structure, see: Osiński et al. (2005 ▶).

Experimental

Crystal data

C42H39NO2P2

M = 651.68

Triclinic,

a = 10.4258 (2) Å

b = 11.1402 (3) Å

c = 15.3590 (4) Å

α = 75.777 (1)°

β = 88.583 (1)°

γ = 79.453 (2)°

V = 1699.60 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.17 mm−1

T = 173 (2) K

0.51 × 0.31 × 0.29 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: none

30269 measured reflections

8211 independent reflections

6458 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.122

S = 1.08

8211 reflections

489 parameters

115 restraints

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT-NT (Bruker, 2005 ▶); data reduction: SAINT-NT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: PLATON (Spek, 2003 ▶) and ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808030134/rt2023sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808030134/rt2023Isup2.hkl

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

C42H39NO2P2	Z = 2
Mr = 651.68	F(000) = 688
Triclinic, P1	Dx = 1.273 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.4258 (2) Å	Cell parameters from 5800 reflections
b = 11.1402 (3) Å	θ = 2.4–28.4°
c = 15.3590 (4) Å	µ = 0.17 mm−1
α = 75.777 (1)°	T = 173 K
β = 88.583 (1)°	Prismic, yellow
γ = 79.453 (2)°	0.51 × 0.31 × 0.29 mm
V = 1699.60 (7) Å3

Bruker SMART CCD area-detector diffractometer	6458 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.043
graphite	θmax = 28.0°, θmin = 1.4°
φ and ω scans	h = −13→13
30269 measured reflections	k = −14→14
8211 independent reflections	l = −20→19

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0654P)2 + 0.218P] where P = (Fo2 + 2Fc2)/3
8211 reflections	(Δ/σ)max = 0.001
489 parameters	Δρmax = 0.42 e Å−3
115 restraints	Δρmin = −0.30 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	Occ. (<1)
C1	0.10850 (18)	0.95659 (15)	0.14870 (12)	0.0403 (4)
C2	0.04581 (16)	1.07476 (14)	0.15453 (11)	0.0341 (4)
H2	0.0560	1.1469	0.1087	0.041*
C3	−0.03150 (17)	1.08802 (15)	0.22679 (12)	0.0386 (4)
H3	−0.0729	1.1698	0.2307	0.046*
C4	−0.04999 (17)	0.98523 (15)	0.29330 (12)	0.0363 (4)
H4	−0.1037	0.9965	0.3426	0.044*
C5	0.00996 (14)	0.86440 (13)	0.28850 (10)	0.0263 (3)
C6	0.08763 (16)	0.85335 (14)	0.21642 (12)	0.0348 (4)
C7	0.21739 (16)	0.71321 (15)	0.14128 (11)	0.0338 (4)
C8	0.26737 (14)	0.58992 (14)	0.14232 (10)	0.0261 (3)
C9	0.34299 (16)	0.56684 (16)	0.07008 (11)	0.0350 (4)
H9	0.3794	0.4827	0.0687	0.042*
C10	0.36543 (17)	0.66473 (17)	0.00077 (11)	0.0381 (4)
H10	0.4169	0.6474	−0.0481	0.046*
C11	0.31406 (16)	0.78831 (16)	0.00116 (11)	0.0347 (4)
H11	0.3297	0.8551	−0.0474	0.042*
C12	0.23980 (18)	0.81449 (15)	0.07248 (12)	0.0393 (4)
C13	0.2513 (3)	1.0437 (2)	0.02672 (16)	0.0311 (6)	0.683 (3)
H13A	0.3408	1.0148	0.0080	0.037*	0.683 (3)
H13B	0.2561	1.1077	0.0607	0.037*	0.683 (3)
C14	0.1672 (2)	1.1065 (2)	−0.05704 (17)	0.0350 (6)	0.683 (3)
H14A	0.0766	1.1336	−0.0394	0.042*	0.683 (3)
H14B	0.1658	1.0449	−0.0936	0.042*	0.683 (3)
C15	0.2183 (2)	1.2209 (2)	−0.11373 (16)	0.0357 (6)	0.683 (3)
H15A	0.1520	1.2685	−0.1606	0.043*	0.683 (3)
H15B	0.2304	1.2770	−0.0748	0.043*	0.683 (3)
C16	0.3457 (4)	1.1862 (4)	−0.1583 (3)	0.0408 (10)	0.683 (3)
H16A	0.4121	1.1400	−0.1111	0.049*	0.683 (3)
H16B	0.3338	1.1283	−0.1959	0.049*	0.683 (3)
C17	0.3969 (4)	1.2969 (4)	−0.2162 (3)	0.0381 (11)	0.683 (3)
H17A	0.4147	1.3514	−0.1775	0.046*	0.683 (3)
H17B	0.3276	1.3467	−0.2602	0.046*	0.683 (3)
C13B	0.1715 (5)	1.0427 (5)	−0.0122 (3)	0.0339 (12)	0.317 (3)
H13C	0.0917	1.1085	−0.0222	0.041*	0.317 (3)
H13D	0.1896	1.0151	−0.0685	0.041*	0.317 (3)
C14B	0.2856 (6)	1.0974 (6)	0.0113 (4)	0.0476 (15)	0.317 (3)
H14C	0.3653	1.0317	0.0193	0.057*	0.317 (3)
H14D	0.2686	1.1205	0.0693	0.057*	0.317 (3)
C15B	0.3105 (7)	1.2130 (5)	−0.0593 (4)	0.0532 (17)	0.317 (3)
H15C	0.2255	1.2677	−0.0802	0.064*	0.317 (3)
H15D	0.3604	1.2610	−0.0306	0.064*	0.317 (3)
C16B	0.3839 (9)	1.1846 (9)	−0.1399 (5)	0.045 (2)	0.317 (3)
H16C	0.3285	1.1491	−0.1747	0.054*	0.317 (3)
H16D	0.4633	1.1206	−0.1193	0.054*	0.317 (3)
C17B	0.4226 (10)	1.3013 (9)	−0.1998 (7)	0.045 (3)	0.317 (3)
H17C	0.3443	1.3578	−0.2316	0.054*	0.317 (3)
H17D	0.4618	1.3473	−0.1630	0.054*	0.317 (3)
C18	0.51909 (17)	1.26407 (17)	−0.26682 (12)	0.0400 (4)
H18A	0.5914	1.2174	−0.2242	0.048*
H18B	0.5038	1.2105	−0.3069	0.048*
C21	0.14465 (15)	0.69008 (15)	0.43719 (10)	0.0297 (3)
C22	0.20133 (17)	0.56556 (16)	0.47588 (11)	0.0374 (4)
H22	0.1618	0.4991	0.4667	0.045*
C23	0.31469 (19)	0.5377 (2)	0.52756 (12)	0.0483 (5)
H23	0.3525	0.4524	0.5536	0.058*
C24	0.37245 (18)	0.6324 (2)	0.54126 (13)	0.0506 (5)
H24	0.4510	0.6127	0.5761	0.061*
C25	0.31694 (18)	0.7565 (2)	0.50468 (14)	0.0477 (5)
H25	0.3559	0.8221	0.5158	0.057*
C26	0.20443 (16)	0.78555 (17)	0.45171 (12)	0.0390 (4)
H26	0.1680	0.8711	0.4252	0.047*
C31	−0.12692 (15)	0.78316 (14)	0.44558 (11)	0.0289 (3)
C32	−0.09950 (16)	0.80924 (17)	0.52627 (11)	0.0360 (4)
H32	−0.0115	0.7957	0.5467	0.043*
C33	−0.19952 (19)	0.85480 (18)	0.57712 (13)	0.0447 (4)
H33	−0.1796	0.8720	0.6323	0.054*
C34	−0.32668 (19)	0.87525 (19)	0.54871 (13)	0.0488 (5)
H34	−0.3948	0.9059	0.5842	0.059*
C35	−0.35526 (18)	0.8513 (2)	0.46878 (15)	0.0544 (5)
H35	−0.4433	0.8669	0.4481	0.065*
C36	−0.25611 (17)	0.80432 (19)	0.41813 (13)	0.0443 (4)
H36	−0.2771	0.7862	0.3634	0.053*
C41	0.35700 (14)	0.33337 (13)	0.22967 (10)	0.0259 (3)
C42	0.32873 (17)	0.22495 (15)	0.21177 (11)	0.0332 (4)
H42	0.2419	0.2223	0.1960	0.040*
C43	0.42648 (18)	0.11970 (16)	0.21672 (12)	0.0401 (4)
H43	0.4058	0.0459	0.2043	0.048*
C44	0.55208 (18)	0.12183 (16)	0.23939 (12)	0.0402 (4)
H44	0.6182	0.0496	0.2431	0.048*
C45	0.58230 (17)	0.22873 (16)	0.25679 (12)	0.0384 (4)
H45	0.6695	0.2305	0.2721	0.046*
C46	0.48592 (15)	0.33387 (15)	0.25208 (11)	0.0327 (4)
H46	0.5078	0.4073	0.2643	0.039*
C51	0.08077 (14)	0.43856 (13)	0.20881 (11)	0.0278 (3)
C52	−0.01832 (16)	0.43793 (14)	0.27117 (12)	0.0335 (4)
H52	−0.0006	0.4460	0.3296	0.040*
C53	−0.14243 (16)	0.42574 (15)	0.24918 (13)	0.0397 (4)
H53	−0.2093	0.4257	0.2924	0.048*
C54	−0.16890 (17)	0.41373 (16)	0.16488 (13)	0.0416 (4)
H54	−0.2546	0.4074	0.1493	0.050*
C55	−0.07114 (17)	0.41088 (16)	0.10282 (12)	0.0381 (4)
H55	−0.0891	0.4002	0.0451	0.046*
C56	0.05286 (16)	0.42354 (15)	0.12440 (11)	0.0334 (4)
H56	0.1196	0.4220	0.0812	0.040*
N1	0.2074 (2)	0.93759 (18)	0.08664 (16)	0.0336 (6)	0.683 (3)
N1B	0.1493 (5)	0.9347 (3)	0.0605 (2)	0.0303 (12)	0.317 (3)
O1	0.1616 (2)	0.73286 (17)	0.22274 (13)	0.0313 (5)	0.683 (3)
O1B	0.1088 (4)	0.7331 (3)	0.1957 (3)	0.0310 (11)	0.317 (3)
O2	0.55085 (14)	1.37799 (13)	−0.31765 (9)	0.0533 (4)
H2A	0.6155	1.3624	−0.3495	0.080*
P1	−0.00697 (4)	0.71914 (4)	0.37224 (3)	0.02700 (11)
P2	0.23648 (4)	0.46903 (3)	0.24223 (3)	0.02641 (11)

	U11	U22	U33	U12	U13	U23
C1	0.0484 (10)	0.0244 (8)	0.0439 (10)	−0.0034 (7)	0.0186 (8)	−0.0049 (7)
C2	0.0402 (9)	0.0205 (7)	0.0384 (9)	−0.0043 (6)	0.0050 (7)	−0.0023 (6)
C3	0.0459 (10)	0.0220 (7)	0.0445 (10)	0.0017 (7)	0.0055 (8)	−0.0081 (7)
C4	0.0406 (9)	0.0274 (8)	0.0384 (9)	0.0002 (7)	0.0085 (7)	−0.0088 (7)
C5	0.0253 (7)	0.0235 (7)	0.0288 (8)	−0.0030 (6)	0.0007 (6)	−0.0053 (6)
C6	0.0393 (9)	0.0198 (7)	0.0409 (9)	0.0003 (6)	0.0120 (7)	−0.0045 (7)
C7	0.0366 (9)	0.0267 (8)	0.0364 (9)	−0.0040 (6)	0.0157 (7)	−0.0074 (7)
C8	0.0260 (7)	0.0249 (7)	0.0275 (8)	−0.0038 (6)	0.0012 (6)	−0.0075 (6)
C9	0.0390 (9)	0.0311 (8)	0.0328 (9)	0.0021 (7)	0.0051 (7)	−0.0106 (7)
C10	0.0397 (9)	0.0426 (9)	0.0305 (9)	−0.0024 (7)	0.0097 (7)	−0.0109 (7)
C11	0.0372 (9)	0.0347 (8)	0.0301 (8)	−0.0071 (7)	0.0086 (7)	−0.0044 (7)
C12	0.0458 (10)	0.0259 (8)	0.0433 (10)	−0.0056 (7)	0.0181 (8)	−0.0055 (7)
C13	0.0376 (14)	0.0273 (12)	0.0290 (12)	−0.0123 (10)	0.0002 (10)	−0.0036 (9)
C14	0.0378 (13)	0.0321 (13)	0.0327 (13)	−0.0079 (10)	−0.0005 (10)	−0.0024 (10)
C15	0.0464 (14)	0.0261 (11)	0.0297 (12)	−0.0035 (10)	0.0017 (10)	0.0000 (9)
C16	0.052 (2)	0.0308 (15)	0.0396 (17)	−0.0127 (14)	0.0084 (15)	−0.0063 (13)
C17	0.058 (2)	0.0271 (15)	0.0310 (17)	−0.0115 (14)	0.0083 (16)	−0.0093 (12)
C13B	0.045 (3)	0.029 (3)	0.027 (3)	−0.009 (2)	0.006 (2)	−0.004 (2)
C14B	0.055 (3)	0.049 (3)	0.049 (3)	−0.028 (3)	0.013 (3)	−0.018 (2)
C15B	0.069 (4)	0.045 (3)	0.057 (3)	−0.031 (3)	0.026 (3)	−0.023 (2)
C16B	0.057 (5)	0.037 (3)	0.050 (4)	−0.022 (3)	0.014 (3)	−0.019 (3)
C17B	0.064 (5)	0.041 (4)	0.039 (4)	−0.025 (3)	0.012 (4)	−0.017 (3)
C18	0.0402 (9)	0.0393 (9)	0.0395 (10)	−0.0092 (7)	−0.0001 (7)	−0.0059 (8)
C21	0.0262 (7)	0.0312 (8)	0.0290 (8)	−0.0011 (6)	0.0053 (6)	−0.0057 (6)
C22	0.0415 (9)	0.0339 (9)	0.0318 (9)	0.0008 (7)	0.0040 (7)	−0.0044 (7)
C23	0.0465 (11)	0.0516 (11)	0.0336 (10)	0.0133 (9)	−0.0009 (8)	−0.0020 (8)
C24	0.0333 (9)	0.0767 (15)	0.0350 (10)	0.0043 (9)	−0.0031 (8)	−0.0111 (10)
C25	0.0340 (9)	0.0641 (13)	0.0479 (11)	−0.0133 (9)	0.0014 (8)	−0.0162 (10)
C26	0.0308 (8)	0.0389 (9)	0.0453 (10)	−0.0067 (7)	0.0012 (7)	−0.0066 (8)
C31	0.0263 (7)	0.0265 (7)	0.0324 (8)	−0.0051 (6)	0.0054 (6)	−0.0049 (6)
C32	0.0313 (8)	0.0427 (9)	0.0333 (9)	−0.0058 (7)	0.0034 (7)	−0.0087 (7)
C33	0.0479 (11)	0.0519 (11)	0.0355 (10)	−0.0082 (9)	0.0119 (8)	−0.0147 (8)
C34	0.0414 (10)	0.0536 (11)	0.0462 (11)	−0.0011 (8)	0.0195 (9)	−0.0098 (9)
C35	0.0274 (9)	0.0783 (15)	0.0539 (12)	−0.0019 (9)	0.0074 (8)	−0.0157 (11)
C36	0.0285 (9)	0.0632 (12)	0.0427 (10)	−0.0077 (8)	0.0024 (7)	−0.0167 (9)
C41	0.0309 (8)	0.0223 (7)	0.0228 (7)	−0.0006 (6)	0.0019 (6)	−0.0055 (6)
C42	0.0385 (9)	0.0286 (8)	0.0331 (9)	−0.0023 (6)	−0.0054 (7)	−0.0110 (7)
C43	0.0545 (11)	0.0266 (8)	0.0395 (10)	0.0015 (7)	−0.0046 (8)	−0.0146 (7)
C44	0.0431 (10)	0.0333 (9)	0.0378 (9)	0.0110 (7)	0.0022 (8)	−0.0099 (7)
C45	0.0295 (8)	0.0385 (9)	0.0420 (10)	0.0003 (7)	0.0021 (7)	−0.0050 (8)
C46	0.0323 (8)	0.0280 (8)	0.0368 (9)	−0.0044 (6)	0.0014 (7)	−0.0067 (7)
C51	0.0272 (7)	0.0208 (7)	0.0320 (8)	−0.0009 (6)	0.0008 (6)	−0.0027 (6)
C52	0.0372 (9)	0.0241 (7)	0.0385 (9)	−0.0036 (6)	0.0081 (7)	−0.0087 (7)
C53	0.0324 (9)	0.0288 (8)	0.0566 (12)	−0.0050 (7)	0.0129 (8)	−0.0094 (8)
C54	0.0313 (9)	0.0296 (8)	0.0584 (12)	−0.0061 (7)	−0.0049 (8)	0.0002 (8)
C55	0.0410 (10)	0.0333 (9)	0.0353 (9)	−0.0093 (7)	−0.0087 (7)	0.0032 (7)
C56	0.0347 (8)	0.0316 (8)	0.0296 (8)	−0.0061 (7)	0.0011 (7)	0.0003 (7)
N1	0.0397 (13)	0.0247 (10)	0.0343 (12)	−0.0076 (9)	0.0098 (11)	−0.0031 (8)
N1B	0.034 (3)	0.022 (2)	0.033 (3)	−0.0073 (18)	0.013 (2)	−0.0041 (18)
O1	0.0354 (12)	0.0214 (8)	0.0294 (11)	0.0051 (8)	0.0100 (9)	−0.0005 (7)
O1B	0.027 (2)	0.0205 (18)	0.038 (3)	0.0042 (17)	0.0124 (19)	0.0000 (17)
O2	0.0518 (8)	0.0506 (8)	0.0500 (8)	−0.0079 (6)	0.0098 (6)	−0.0001 (6)
P1	0.0266 (2)	0.02380 (19)	0.0298 (2)	−0.00413 (15)	0.00407 (15)	−0.00582 (16)
P2	0.0285 (2)	0.02239 (19)	0.0277 (2)	−0.00139 (14)	0.00210 (15)	−0.00764 (15)

C1—C2	1.381 (2)	C16B—H16D	0.9900
C1—C6	1.394 (2)	C17B—C18	1.500 (5)
C1—N1	1.410 (2)	C17B—H17C	0.9900
C1—N1B	1.474 (3)	C17B—H17D	0.9900
C2—C3	1.377 (2)	C18—O2	1.408 (2)
C2—H2	0.9500	C18—H18A	0.9900
C3—C4	1.374 (2)	C18—H18B	0.9900
C3—H3	0.9500	C21—C26	1.391 (2)
C4—C5	1.395 (2)	C21—C22	1.392 (2)
C4—H4	0.9500	C21—P1	1.8250 (16)
C5—C6	1.372 (2)	C22—C23	1.384 (3)
C5—P1	1.8370 (15)	C22—H22	0.9500
C6—O1	1.402 (2)	C23—C24	1.366 (3)
C6—O1B	1.429 (3)	C23—H23	0.9500
C7—C8	1.373 (2)	C24—C25	1.380 (3)
C7—C12	1.394 (2)	C24—H24	0.9500
C7—O1B	1.408 (3)	C25—C26	1.386 (2)
C7—O1	1.415 (2)	C25—H25	0.9500
C8—C9	1.393 (2)	C26—H26	0.9500
C8—P2	1.8414 (15)	C31—C36	1.382 (2)
C9—C10	1.374 (2)	C31—C32	1.388 (2)
C9—H9	0.9500	C31—P1	1.8275 (16)
C10—C11	1.384 (2)	C32—C33	1.384 (2)
C10—H10	0.9500	C32—H32	0.9500
C11—C12	1.385 (2)	C33—C34	1.367 (3)
C11—H11	0.9500	C33—H33	0.9500
C12—N1	1.420 (2)	C34—C35	1.369 (3)
C12—N1B	1.464 (3)	C34—H34	0.9500
C13—N1	1.448 (3)	C35—C36	1.382 (3)
C13—C14	1.517 (3)	C35—H35	0.9500
C13—H13A	0.9900	C36—H36	0.9500
C13—H13B	0.9900	C41—C42	1.385 (2)
C14—C15	1.532 (3)	C41—C46	1.397 (2)
C14—H14A	0.9900	C41—P2	1.8264 (14)
C14—H14B	0.9900	C42—C43	1.393 (2)
C15—C16	1.510 (4)	C42—H42	0.9500
C15—H15A	0.9900	C43—C44	1.369 (3)
C15—H15B	0.9900	C43—H43	0.9500
C16—C17	1.508 (3)	C44—C45	1.374 (3)
C16—H16A	0.9900	C44—H44	0.9500
C16—H16B	0.9900	C45—C46	1.385 (2)
C17—C18	1.510 (3)	C45—H45	0.9500
C17—H17A	0.9900	C46—H46	0.9500
C17—H17B	0.9900	C51—C52	1.391 (2)
C13B—N1B	1.474 (4)	C51—C56	1.392 (2)
C13B—C14B	1.520 (5)	C51—P2	1.8284 (16)
C13B—H13C	0.9900	C52—C53	1.384 (2)
C13B—H13D	0.9900	C52—H52	0.9500
C14B—C15B	1.524 (5)	C53—C54	1.374 (3)
C14B—H14C	0.9900	C53—H53	0.9500
C14B—H14D	0.9900	C54—C55	1.380 (3)
C15B—C16B	1.508 (5)	C54—H54	0.9500
C15B—H15C	0.9900	C55—C56	1.383 (2)
C15B—H15D	0.9900	C55—H55	0.9500
C16B—C17B	1.512 (5)	C56—H56	0.9500
C16B—H16C	0.9900	O2—H2A	0.8400
C2—C1—C6	117.85 (15)	C16B—C17B—H17C	109.8
C2—C1—N1	122.95 (16)	C18—C17B—H17D	109.8
C6—C1—N1	118.37 (15)	C16B—C17B—H17D	109.8
C2—C1—N1B	119.71 (19)	H17C—C17B—H17D	108.2
C6—C1—N1B	117.95 (19)	O2—C18—C17B	105.1 (4)
C3—C2—C1	120.00 (15)	O2—C18—C17	107.4 (2)
C3—C2—H2	120.0	O2—C18—H18A	110.2
C1—C2—H2	120.0	C17B—C18—H18A	98.1
C4—C3—C2	121.30 (15)	C17—C18—H18A	110.2
C4—C3—H3	119.4	O2—C18—H18B	110.2
C2—C3—H3	119.4	C17B—C18—H18B	123.7
C3—C4—C5	120.09 (15)	C17—C18—H18B	110.2
C3—C4—H4	120.0	H18A—C18—H18B	108.5
C5—C4—H4	120.0	C26—C21—C22	118.56 (15)
C6—C5—C4	117.69 (14)	C26—C21—P1	123.49 (12)
C6—C5—P1	117.70 (11)	C22—C21—P1	117.93 (13)
C4—C5—P1	124.60 (12)	C23—C22—C21	120.57 (18)
C5—C6—C1	123.05 (14)	C23—C22—H22	119.7
C5—C6—O1	114.86 (15)	C21—C22—H22	119.7
C1—C6—O1	121.33 (15)	C24—C23—C22	120.29 (18)
C5—C6—O1B	115.83 (19)	C24—C23—H23	119.9
C1—C6—O1B	117.6 (2)	C22—C23—H23	119.9
C8—C7—C12	123.22 (14)	C23—C24—C25	120.13 (18)
C8—C7—O1B	115.96 (19)	C23—C24—H24	119.9
C12—C7—O1B	117.7 (2)	C25—C24—H24	119.9
C8—C7—O1	115.02 (15)	C24—C25—C26	120.11 (19)
C12—C7—O1	120.76 (15)	C24—C25—H25	119.9
C7—C8—C9	117.48 (14)	C26—C25—H25	119.9
C7—C8—P2	117.19 (11)	C25—C26—C21	120.32 (17)
C9—C8—P2	125.24 (11)	C25—C26—H26	119.8
C10—C9—C8	120.60 (15)	C21—C26—H26	119.8
C10—C9—H9	119.7	C36—C31—C32	118.01 (15)
C8—C9—H9	119.7	C36—C31—P1	116.18 (13)
C9—C10—C11	120.92 (15)	C32—C31—P1	125.79 (12)
C9—C10—H10	119.5	C33—C32—C31	120.40 (16)
C11—C10—H10	119.5	C33—C32—H32	119.8
C10—C11—C12	119.90 (15)	C31—C32—H32	119.8
C10—C11—H11	120.1	C34—C33—C32	120.68 (18)
C12—C11—H11	120.1	C34—C33—H33	119.7
C11—C12—C7	117.88 (14)	C32—C33—H33	119.7
C11—C12—N1	122.58 (16)	C33—C34—C35	119.63 (17)
C7—C12—N1	118.43 (16)	C33—C34—H34	120.2
C11—C12—N1B	119.68 (19)	C35—C34—H34	120.2
C7—C12—N1B	118.50 (19)	C34—C35—C36	120.06 (18)
N1—C13—C14	115.7 (2)	C34—C35—H35	120.0
N1—C13—H13A	108.4	C36—C35—H35	120.0
C14—C13—H13A	108.4	C35—C36—C31	121.21 (18)
N1—C13—H13B	108.4	C35—C36—H36	119.4
C14—C13—H13B	108.4	C31—C36—H36	119.4
H13A—C13—H13B	107.4	C42—C41—C46	118.02 (14)
C13—C14—C15	111.7 (2)	C42—C41—P2	125.36 (12)
C13—C14—H14A	109.3	C46—C41—P2	116.03 (11)
C15—C14—H14A	109.3	C41—C42—C43	120.58 (16)
C13—C14—H14B	109.3	C41—C42—H42	119.7
C15—C14—H14B	109.3	C43—C42—H42	119.7
H14A—C14—H14B	107.9	C44—C43—C42	120.48 (16)
C16—C15—C14	113.2 (2)	C44—C43—H43	119.8
C16—C15—H15A	108.9	C42—C43—H43	119.8
C14—C15—H15A	108.9	C43—C44—C45	119.83 (15)
C16—C15—H15B	108.9	C43—C44—H44	120.1
C14—C15—H15B	108.9	C45—C44—H44	120.1
H15A—C15—H15B	107.7	C44—C45—C46	120.17 (16)
C17—C16—C15	114.4 (3)	C44—C45—H45	119.9
C17—C16—H16A	108.7	C46—C45—H45	119.9
C15—C16—H16A	108.7	C45—C46—C41	120.91 (15)
C17—C16—H16B	108.7	C45—C46—H46	119.5
C15—C16—H16B	108.7	C41—C46—H46	119.5
H16A—C16—H16B	107.6	C52—C51—C56	118.34 (15)
C16—C17—C18	115.4 (3)	C52—C51—P2	116.88 (12)
C16—C17—H17A	108.4	C56—C51—P2	124.67 (12)
C18—C17—H17A	108.4	C53—C52—C51	120.89 (16)
C16—C17—H17B	108.4	C53—C52—H52	119.6
C18—C17—H17B	108.4	C51—C52—H52	119.6
H17A—C17—H17B	107.5	C54—C53—C52	119.95 (16)
N1B—C13B—C14B	111.0 (5)	C54—C53—H53	120.0
N1B—C13B—H13C	109.4	C52—C53—H53	120.0
C14B—C13B—H13C	109.4	C53—C54—C55	120.06 (16)
N1B—C13B—H13D	109.4	C53—C54—H54	120.0
C14B—C13B—H13D	109.4	C55—C54—H54	120.0
H13C—C13B—H13D	108.0	C54—C55—C56	120.15 (17)
C13B—C14B—C15B	113.8 (4)	C54—C55—H55	119.9
C13B—C14B—H14C	108.8	C56—C55—H55	119.9
C15B—C14B—H14C	108.8	C55—C56—C51	120.58 (16)
C13B—C14B—H14D	108.8	C55—C56—H56	119.7
C15B—C14B—H14D	108.8	C51—C56—H56	119.7
H14C—C14B—H14D	107.7	C1—N1—C12	116.48 (16)
C16B—C15B—C14B	114.8 (5)	C1—N1—C13	120.66 (18)
C16B—C15B—H15C	108.6	C12—N1—C13	121.43 (18)
C14B—C15B—H15C	108.6	C12—N1B—C13B	119.2 (3)
C16B—C15B—H15D	108.6	C12—N1B—C1	109.9 (3)
C14B—C15B—H15D	108.6	C13B—N1B—C1	118.8 (3)
H15C—C15B—H15D	107.5	C6—O1—C7	114.79 (16)
C15B—C16B—C17B	111.7 (5)	C7—O1B—C6	113.6 (3)
C15B—C16B—H16C	109.3	C18—O2—H2A	109.5
C17B—C16B—H16C	109.3	C21—P1—C31	102.21 (7)
C15B—C16B—H16D	109.3	C21—P1—C5	100.61 (7)
C17B—C16B—H16D	109.3	C31—P1—C5	100.22 (7)
H16C—C16B—H16D	107.9	C41—P2—C51	104.89 (7)
C18—C17B—C16B	109.4 (5)	C41—P2—C8	101.27 (7)
C18—C17B—H17C	109.8	C51—P2—C8	100.21 (7)
C6—C1—C2—C3	1.7 (3)	C43—C44—C45—C46	0.5 (3)
N1—C1—C2—C3	−167.7 (2)	C44—C45—C46—C41	0.0 (3)
N1B—C1—C2—C3	157.4 (3)	C42—C41—C46—C45	−0.4 (2)
C1—C2—C3—C4	−1.2 (3)	P2—C41—C46—C45	171.23 (13)
C2—C3—C4—C5	0.0 (3)	C56—C51—C52—C53	−1.5 (2)
C3—C4—C5—C6	0.7 (3)	P2—C51—C52—C53	174.79 (12)
C3—C4—C5—P1	−179.70 (14)	C51—C52—C53—C54	0.2 (2)
C4—C5—C6—C1	−0.1 (3)	C52—C53—C54—C55	1.5 (2)
P1—C5—C6—C1	−179.75 (15)	C53—C54—C55—C56	−1.8 (2)
C4—C5—C6—O1	170.02 (18)	C54—C55—C56—C51	0.4 (2)
P1—C5—C6—O1	−9.6 (2)	C52—C51—C56—C55	1.3 (2)
C4—C5—C6—O1B	−158.4 (3)	P2—C51—C56—C55	−174.75 (12)
P1—C5—C6—O1B	22.0 (3)	C2—C1—N1—C12	−164.7 (2)
C2—C1—C6—C5	−1.1 (3)	C6—C1—N1—C12	26.0 (3)
N1—C1—C6—C5	168.8 (2)	N1B—C1—N1—C12	−71.4 (3)
N1B—C1—C6—C5	−157.2 (3)	C2—C1—N1—C13	1.9 (4)
C2—C1—C6—O1	−170.58 (19)	C6—C1—N1—C13	−167.5 (2)
N1—C1—C6—O1	−0.7 (3)	N1B—C1—N1—C13	95.1 (5)
N1B—C1—C6—O1	33.3 (3)	C11—C12—N1—C1	166.2 (2)
C2—C1—C6—O1B	156.8 (3)	C7—C12—N1—C1	−26.1 (3)
N1—C1—C6—O1B	−33.3 (3)	N1B—C12—N1—C1	72.3 (3)
N1B—C1—C6—O1B	0.7 (4)	C11—C12—N1—C13	−0.2 (4)
C12—C7—C8—C9	−0.6 (3)	C7—C12—N1—C13	167.4 (2)
O1B—C7—C8—C9	159.0 (3)	N1B—C12—N1—C13	−94.1 (5)
O1—C7—C8—C9	−169.19 (17)	C14—C13—N1—C1	−81.6 (3)
C12—C7—C8—P2	176.11 (14)	C14—C13—N1—C12	84.3 (3)
O1B—C7—C8—P2	−24.3 (3)	C11—C12—N1B—C13B	−22.6 (6)
O1—C7—C8—P2	7.5 (2)	C7—C12—N1B—C13B	−179.8 (4)
C7—C8—C9—C10	−0.2 (2)	N1—C12—N1B—C13B	82.0 (6)
P2—C8—C9—C10	−176.62 (13)	C11—C12—N1B—C1	−164.8 (2)
C8—C9—C10—C11	0.3 (3)	C7—C12—N1B—C1	38.0 (4)
C9—C10—C11—C12	0.5 (3)	N1—C12—N1B—C1	−60.2 (3)
C10—C11—C12—C7	−1.3 (3)	C14B—C13B—N1B—C12	−74.1 (6)
C10—C11—C12—N1	166.5 (2)	C14B—C13B—N1B—C1	64.7 (6)
C10—C11—C12—N1B	−158.6 (3)	C2—C1—N1B—C12	166.4 (2)
C8—C7—C12—C11	1.3 (3)	C6—C1—N1B—C12	−37.9 (4)
O1B—C7—C12—C11	−158.0 (3)	N1—C1—N1B—C12	61.1 (3)
O1—C7—C12—C11	169.31 (19)	C2—C1—N1B—C13B	24.1 (6)
C8—C7—C12—N1	−166.94 (19)	C6—C1—N1B—C13B	179.8 (4)
O1B—C7—C12—N1	33.8 (3)	N1—C1—N1B—C13B	−81.2 (6)
O1—C7—C12—N1	1.1 (3)	C5—C6—O1—C7	165.88 (18)
C8—C7—C12—N1B	158.9 (3)	C1—C6—O1—C7	−23.8 (3)
O1B—C7—C12—N1B	−0.3 (4)	O1B—C6—O1—C7	67.1 (4)
O1—C7—C12—N1B	−33.1 (3)	C8—C7—O1—C6	−167.55 (18)
N1—C13—C14—C15	177.5 (2)	C12—C7—O1—C6	23.5 (3)
C13—C14—C15—C16	69.7 (3)	O1B—C7—O1—C6	−68.7 (4)
C14—C15—C16—C17	178.8 (3)	C8—C7—O1B—C6	160.1 (3)
C15—C16—C17—C18	−175.8 (4)	C12—C7—O1B—C6	−39.1 (5)
N1B—C13B—C14B—C15B	−177.6 (4)	O1—C7—O1B—C6	65.0 (4)
C13B—C14B—C15B—C16B	−79.7 (8)	C5—C6—O1B—C7	−161.6 (3)
C14B—C15B—C16B—C17B	−171.5 (8)	C1—C6—O1B—C7	38.9 (5)
C15B—C16B—C17B—C18	167.7 (8)	O1—C6—O1B—C7	−66.6 (3)
C16B—C17B—C18—O2	−178.7 (7)	C26—C21—P1—C31	−70.00 (15)
C16B—C17B—C18—C17	80.3 (18)	C22—C21—P1—C31	108.41 (13)
C16—C17—C18—O2	179.2 (3)	C26—C21—P1—C5	33.01 (15)
C16—C17—C18—C17B	−97.5 (19)	C22—C21—P1—C5	−148.57 (13)
C26—C21—C22—C23	0.0 (2)	C36—C31—P1—C21	−174.17 (13)
P1—C21—C22—C23	−178.52 (13)	C32—C31—P1—C21	4.35 (16)
C21—C22—C23—C24	0.0 (3)	C36—C31—P1—C5	82.51 (14)
C22—C23—C24—C25	1.0 (3)	C32—C31—P1—C5	−98.97 (15)
C23—C24—C25—C26	−1.9 (3)	C6—C5—P1—C21	79.94 (14)
C24—C25—C26—C21	1.9 (3)	C4—C5—P1—C21	−99.67 (15)
C22—C21—C26—C25	−0.9 (3)	C6—C5—P1—C31	−175.44 (13)
P1—C21—C26—C25	177.50 (14)	C4—C5—P1—C31	4.94 (16)
C36—C31—C32—C33	0.1 (3)	C42—C41—P2—C51	−8.63 (15)
P1—C31—C32—C33	−178.37 (14)	C46—C41—P2—C51	−179.58 (12)
C31—C32—C33—C34	−0.2 (3)	C42—C41—P2—C8	−112.52 (14)
C32—C33—C34—C35	−0.5 (3)	C46—C41—P2—C8	76.54 (13)
C33—C34—C35—C36	1.3 (3)	C52—C51—P2—C41	123.64 (12)
C34—C35—C36—C31	−1.4 (3)	C56—C51—P2—C41	−60.29 (14)
C32—C31—C36—C35	0.7 (3)	C52—C51—P2—C8	−131.68 (12)
P1—C31—C36—C35	179.31 (17)	C56—C51—P2—C8	44.39 (14)
C46—C41—C42—C43	0.4 (2)	C7—C8—P2—C41	−163.73 (13)
P2—C41—C42—C43	−170.36 (13)	C9—C8—P2—C41	12.66 (16)
C41—C42—C43—C44	0.0 (3)	C7—C8—P2—C51	88.68 (13)
C42—C43—C44—C45	−0.5 (3)	C9—C8—P2—C51	−94.93 (15)