Methyl 3-[4,6-bis­(diphenyl­phosphino)phenoxazin-10-yl]propionate

In the title compound, C₄₀H₃₃NO₃P₂, used as a nixantphos-type ligand in homogeneous catalysis, the central phenoxazine ring system is nearly planar. The most important feature of the mol­ecule is the intra­molecular P...P distance of 4.2346 (13) Å. The angles involving the P atoms are in the range 100.90 (13)–103.40 (16)°.

Key indicators

• Single-crystal X-ray study
• T = 291 K
• Mean [sigma](C-C) = 0.006 Å
• Disorder in main residue
• R factor = 0.038
• wR factor = 0.088
• Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low ....         33 Perc.
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        O3'

Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.78 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O1
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O3
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C45
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C63
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C3
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C41
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C51
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C61
PLAT301_ALERT_3_C Main Residue  Disorder .........................       2.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C40 H33 N O3 P2

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
  12 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  10 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97, PARST95 (Nardelli, 1995) and PLATON (Spek, 2003).

Methyl 3-[4,6-bis(diphenylphosphino)phenoxazin-10-yl]propionate

Crystal data

C40H33NO3P2	Z = 2
Mr = 637.61	F(000) = 668
Triclinic, P1	Dx = 1.268 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.431 (2) Å	Cell parameters from 21372 reflections
b = 11.354 (2) Å	θ = 3.0–25.4°
c = 15.337 (3) Å	µ = 0.17 mm^−1
α = 68.961 (6)°	T = 291 K
β = 84.619 (10)°	Plate, pale yellow
γ = 80.182 (9)°	0.26 × 0.16 × 0.08 mm
V = 1669.5 (5) Å^3

Data collection

Nonius KappaCCD diffractometer	2007 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.033
Graphite monochromator	θmax = 25.4°, θmin = 3.0°
Detector resolution: 19 vertical, 18 horizontal pixels mm^-1	h = −12→12
235 frames via ω–rotation (Δω=2°) and two times 75 s per frame (five sets at different κ–angles) scans	k = −13→13
21372 measured reflections	l = −18→18
6052 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.088	H-atom parameters constrained
S = 1.01	w = [exp{4.20(sinθ/λ}^2)]/[σ^2(Fo^2)]
6052 reflections	(Δ/σ)max < 0.001
424 parameters	Δρmax = 0.22 e Å^−3
0 restraints	Δρmin = −0.15 e Å^−3

Special details

Experimental. ¹H NMR (500 MHz, C₆D₆): δ 2.27 (t, 2H,J = 7.5 Hz), 3.36 (s, 3H), 3.52 (t, 2H, J = 7.5 Hz), 6.22 (d, 2H, J = 8.0 Hz), 6.41 (d, 2H, J = 7.5 Hz), 6.54 (dd, 2H, J = 7.5, J = 8.0 Hz), 7.1 (bs, 12H), 7.5 (bs, 8H); ¹³C NMR (125 MHz, C₆D₆): δ 30.8 (CH₂), 41.2 (CH₂), 52.5 (CH₃), 113.2 (CH), 125.5 (CH), 127.2 (CH), 129.8 (m, CH), 134.1 (C), 135.7 (m, CH), 139.0 (C), 139.0 (C), 172.6 (C); ³¹P NMR (81 MHz, C₆D₆): δ -17.5; IR (KBr plate; ν cm^-1): 694 (s), 744 (s), 1222 (s), 1279 (s), 1377 (s), 1417 (vs), 1462 (s), 1552 (s), 1577 (m), 1724 (s), 2949 (w), 2999 (w), 3051 (w), 3064 (w)

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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
P1	−0.21268 (9)	0.76267 (8)	0.23814 (6)	0.0887 (3)
P2	0.01709 (8)	0.39899 (8)	0.34018 (6)	0.0825 (3)
N1	−0.1786 (2)	0.5021 (2)	0.02021 (16)	0.0883 (8)
O1	−0.12040 (19)	0.55383 (18)	0.17535 (13)	0.0928 (7)
O2	−0.4265 (3)	0.3867 (3)	−0.1688 (2)	0.1552 (11)
O3	−0.4828 (8)	0.5587 (10)	−0.1623 (7)	0.179 (3)	0.50
O3'	−0.3610 (10)	0.5618 (12)	−0.2104 (5)	0.184 (4)	0.50
C1	−0.2057 (3)	0.4790 (3)	−0.0632 (2)	0.0989 (10)
H1A	−0.1326	0.4227	−0.0775	0.119*
H1B	−0.2135	0.5593	−0.1154	0.119*
C2	−0.3286 (3)	0.4203 (3)	−0.0538 (2)	0.1104 (12)
H2A	−0.3066	0.3282	−0.0328	0.132*
H2B	−0.3871	0.4418	−0.0069	0.132*
C3	−0.3955 (7)	0.4659 (4)	−0.1434 (4)	0.1271 (16)
C4	−0.4983 (4)	0.4368 (5)	−0.2563 (3)	0.207 (2)
H4A	−0.5213	0.3671	−0.2700	0.310*
H4B	−0.4443	0.4838	−0.3065	0.310*
H4C	−0.5759	0.4921	−0.2491	0.310*
C11	−0.2565 (3)	0.7506 (3)	0.12879 (19)	0.0788 (9)
C12	−0.2070 (3)	0.6397 (3)	0.1111 (2)	0.0764 (8)
C13	−0.2370 (3)	0.6151 (3)	0.0334 (2)	0.0794 (9)
C14	−0.3243 (3)	0.7058 (3)	−0.0275 (2)	0.0949 (10)
H14A	−0.3487	0.6916	−0.0793	0.114*
C15	−0.3757 (3)	0.8174 (3)	−0.0121 (2)	0.1071 (12)
H15A	−0.4334	0.8780	−0.0541	0.129*
C16	−0.3427 (3)	0.8404 (3)	0.0647 (2)	0.0988 (11)
H16A	−0.3780	0.9163	0.0738	0.119*
C21	−0.0109 (3)	0.3461 (3)	0.2448 (2)	0.0747 (8)
C22	−0.0809 (3)	0.4329 (3)	0.1706 (2)	0.0749 (8)
C23	−0.1083 (3)	0.4068 (3)	0.0927 (2)	0.0783 (8)
C24	−0.0598 (3)	0.2863 (3)	0.0902 (2)	0.0917 (10)
H24A	−0.0770	0.2645	0.0399	0.110*
C25	0.0138 (3)	0.1988 (3)	0.1620 (3)	0.1004 (11)
H25A	0.0477	0.1192	0.1587	0.120*
C26	0.0380 (3)	0.2268 (3)	0.2385 (2)	0.0907 (10)
H26A	0.0873	0.1660	0.2863	0.109*
C31	−0.3145 (4)	0.9125 (3)	0.2354 (2)	0.0818 (9)
C32	−0.4383 (4)	0.9043 (3)	0.2755 (2)	0.1052 (11)
H32A	−0.4660	0.8248	0.3007	0.126*
C33	−0.5229 (4)	1.0112 (5)	0.2795 (3)	0.1156 (13)
H33A	−0.6066	1.0034	0.3055	0.139*
C34	−0.4817 (4)	1.1270 (4)	0.2450 (3)	0.1081 (14)
H34A	−0.5370	1.1989	0.2483	0.130*
C35	−0.3588 (4)	1.1386 (3)	0.2053 (2)	0.1015 (11)
H35A	−0.3310	1.2180	0.1819	0.122*
C36	−0.2757 (3)	1.0308 (3)	0.2002 (2)	0.0919 (10)
H36A	−0.1930	1.0393	0.1725	0.110*
C41	−0.0491 (3)	0.8074 (3)	0.2077 (3)	0.0856 (10)
C42	0.0046 (4)	0.8527 (3)	0.1179 (3)	0.1004 (11)
H42A	−0.0445	0.8634	0.0673	0.121*
C43	0.1297 (5)	0.8822 (3)	0.1023 (3)	0.1187 (13)
H43A	0.1641	0.9117	0.0415	0.142*
C44	0.2038 (4)	0.8686 (4)	0.1755 (5)	0.1404 (18)
H44A	0.2878	0.8891	0.1649	0.168*
C45	0.1517 (6)	0.8244 (4)	0.2640 (4)	0.147 (2)
H45A	0.2011	0.8152	0.3142	0.177*
C46	0.0273 (5)	0.7931 (3)	0.2809 (3)	0.1198 (13)
H46A	−0.0055	0.7620	0.3421	0.144*
C51	0.1147 (3)	0.2565 (3)	0.4182 (2)	0.0771 (9)
C52	0.2475 (4)	0.2475 (3)	0.4081 (2)	0.1078 (11)
H52A	0.2845	0.3119	0.3613	0.129*
C53	0.3281 (4)	0.1443 (4)	0.4662 (3)	0.1188 (13)
H53A	0.4180	0.1392	0.4567	0.143*
C54	0.2772 (4)	0.0514 (4)	0.5363 (3)	0.1106 (13)
H54A	0.3317	−0.0166	0.5757	0.133*
C55	0.1470 (4)	0.0576 (4)	0.5488 (2)	0.1218 (13)
H55A	0.1114	−0.0065	0.5967	0.146*
C56	0.0660 (3)	0.1597 (4)	0.4901 (3)	0.1075 (11)
H56A	−0.0237	0.1629	0.4996	0.129*
C61	−0.1402 (3)	0.3895 (3)	0.4025 (2)	0.0812 (9)
C62	−0.1714 (4)	0.4566 (3)	0.4633 (3)	0.1097 (12)
H62A	−0.1135	0.5075	0.4684	0.132*
C63	−0.2851 (6)	0.4500 (5)	0.5158 (3)	0.1447 (17)
H63A	−0.3040	0.4979	0.5547	0.174*
C64	−0.3709 (5)	0.3748 (5)	0.5122 (3)	0.1387 (17)
H64A	−0.4465	0.3680	0.5498	0.166*
C65	−0.3436 (4)	0.3094 (4)	0.4521 (4)	0.1334 (15)
H65A	−0.4023	0.2590	0.4475	0.160*
C66	−0.2304 (4)	0.3168 (3)	0.3981 (3)	0.1103 (12)
H66A	−0.2143	0.2714	0.3574	0.132*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.1258 (8)	0.0651 (6)	0.0755 (6)	0.0018 (5)	−0.0209 (5)	−0.0278 (5)
P2	0.0892 (6)	0.0701 (6)	0.0896 (6)	−0.0043 (5)	−0.0158 (5)	−0.0297 (5)
N1	0.121 (2)	0.0823 (19)	0.0713 (17)	−0.0030 (17)	−0.0139 (16)	−0.0411 (16)
O1	0.1241 (17)	0.0707 (14)	0.0902 (15)	0.0135 (13)	−0.0392 (13)	−0.0399 (12)
O2	0.208 (3)	0.145 (3)	0.133 (2)	−0.053 (2)	−0.036 (2)	−0.054 (2)
O3	0.240 (8)	0.112 (5)	0.168 (7)	0.047 (7)	−0.097 (7)	−0.040 (5)
O3'	0.252 (10)	0.164 (7)	0.121 (6)	−0.106 (7)	−0.081 (6)	0.020 (6)
C1	0.125 (3)	0.095 (3)	0.083 (2)	−0.018 (2)	0.001 (2)	−0.040 (2)
C2	0.127 (3)	0.100 (3)	0.109 (3)	−0.014 (2)	−0.027 (2)	−0.038 (2)
C3	0.204 (5)	0.077 (3)	0.108 (4)	−0.018 (4)	−0.064 (4)	−0.029 (3)
C4	0.250 (5)	0.299 (6)	0.101 (3)	−0.130 (5)	−0.040 (3)	−0.057 (4)
C11	0.101 (2)	0.061 (2)	0.074 (2)	−0.0036 (18)	−0.0150 (18)	−0.0238 (17)
C12	0.091 (2)	0.067 (2)	0.071 (2)	−0.0042 (18)	−0.0142 (18)	−0.0248 (18)
C13	0.096 (2)	0.070 (2)	0.074 (2)	−0.0055 (19)	−0.0109 (18)	−0.0286 (19)
C14	0.126 (3)	0.084 (2)	0.078 (2)	−0.003 (2)	−0.025 (2)	−0.033 (2)
C15	0.144 (3)	0.087 (3)	0.085 (3)	0.008 (2)	−0.039 (2)	−0.026 (2)
C16	0.130 (3)	0.076 (2)	0.090 (2)	0.013 (2)	−0.032 (2)	−0.035 (2)
C21	0.077 (2)	0.064 (2)	0.082 (2)	−0.0027 (17)	−0.0089 (17)	−0.0265 (18)
C22	0.084 (2)	0.062 (2)	0.088 (2)	−0.0079 (17)	−0.0045 (18)	−0.0379 (19)
C23	0.089 (2)	0.071 (2)	0.081 (2)	−0.0113 (18)	−0.0017 (18)	−0.034 (2)
C24	0.106 (3)	0.088 (3)	0.095 (3)	−0.008 (2)	−0.006 (2)	−0.052 (2)
C25	0.110 (3)	0.083 (2)	0.121 (3)	0.007 (2)	−0.014 (2)	−0.058 (2)
C26	0.099 (2)	0.072 (2)	0.105 (3)	−0.0014 (19)	−0.014 (2)	−0.037 (2)
C31	0.107 (3)	0.069 (2)	0.071 (2)	−0.004 (2)	−0.012 (2)	−0.0276 (19)
C32	0.121 (3)	0.092 (3)	0.116 (3)	−0.016 (3)	−0.009 (3)	−0.051 (2)
C33	0.105 (3)	0.131 (4)	0.127 (3)	−0.002 (3)	−0.009 (2)	−0.069 (3)
C34	0.133 (4)	0.102 (3)	0.087 (3)	0.027 (3)	−0.030 (3)	−0.044 (3)
C35	0.144 (3)	0.068 (3)	0.083 (3)	0.005 (3)	−0.013 (2)	−0.022 (2)
C36	0.117 (3)	0.073 (2)	0.080 (2)	0.004 (2)	−0.0046 (19)	−0.028 (2)
C41	0.107 (3)	0.064 (2)	0.088 (2)	0.0126 (19)	−0.034 (2)	−0.033 (2)
C42	0.111 (3)	0.095 (3)	0.106 (3)	0.000 (2)	−0.017 (3)	−0.052 (3)
C43	0.109 (3)	0.102 (3)	0.154 (4)	−0.001 (3)	−0.003 (3)	−0.062 (3)
C44	0.111 (4)	0.102 (4)	0.208 (5)	0.010 (3)	−0.050 (4)	−0.054 (4)
C45	0.156 (5)	0.121 (4)	0.155 (5)	−0.018 (3)	−0.073 (4)	−0.019 (4)
C46	0.147 (4)	0.099 (3)	0.109 (3)	−0.009 (3)	−0.047 (3)	−0.025 (2)
C51	0.071 (2)	0.077 (2)	0.083 (2)	−0.0027 (18)	−0.0124 (18)	−0.031 (2)
C52	0.089 (3)	0.098 (3)	0.129 (3)	−0.008 (2)	−0.012 (2)	−0.031 (2)
C53	0.079 (3)	0.123 (4)	0.147 (4)	0.008 (3)	−0.025 (3)	−0.044 (3)
C54	0.108 (4)	0.109 (3)	0.117 (3)	0.019 (3)	−0.042 (3)	−0.048 (3)
C55	0.107 (3)	0.107 (3)	0.119 (3)	0.007 (3)	−0.028 (3)	−0.006 (2)
C56	0.087 (3)	0.102 (3)	0.114 (3)	0.002 (2)	−0.022 (2)	−0.017 (2)
C61	0.083 (2)	0.071 (2)	0.084 (2)	0.0079 (19)	−0.0173 (19)	−0.0251 (19)
C62	0.120 (3)	0.112 (3)	0.102 (3)	−0.004 (2)	−0.003 (2)	−0.050 (3)
C63	0.158 (5)	0.144 (5)	0.125 (4)	0.001 (4)	0.035 (4)	−0.058 (3)
C64	0.114 (4)	0.122 (4)	0.136 (4)	0.019 (3)	0.022 (3)	−0.014 (3)
C65	0.093 (3)	0.129 (4)	0.176 (4)	−0.010 (3)	0.008 (3)	−0.056 (3)
C66	0.086 (3)	0.122 (3)	0.134 (3)	−0.006 (3)	−0.003 (3)	−0.063 (3)

Geometric parameters (Å, º)

P1—C41	1.834 (4)	C31—C36	1.372 (4)
P1—C31	1.835 (3)	C31—C32	1.381 (4)
P1—C11	1.836 (3)	C32—C33	1.389 (4)
P1—P2	4.2346 (13)	C32—H32A	0.9300
P2—C61	1.819 (3)	C33—C34	1.358 (4)
P2—C21	1.833 (3)	C33—H33A	0.9300
P2—C51	1.834 (3)	C34—C35	1.372 (4)
N1—C13	1.398 (3)	C34—H34A	0.9300
N1—C23	1.401 (3)	C35—C36	1.396 (4)
N1—C1	1.456 (3)	C35—H35A	0.9300
O1—C12	1.383 (3)	C36—H36A	0.9300
O1—C22	1.391 (3)	C41—C46	1.384 (4)
O2—C3	1.200 (4)	C41—C42	1.385 (4)
O2—C4	1.476 (4)	C42—C43	1.381 (4)
O3—C3	1.236 (6)	C42—H42A	0.9300
O3—O3'	1.407 (9)	C43—C44	1.370 (5)
O3'—C3	1.277 (7)	C43—H43A	0.9300
C1—C2	1.516 (4)	C44—C45	1.362 (5)
C1—H1A	0.9700	C44—H44A	0.9300
C1—H1B	0.9700	C45—C46	1.381 (5)
C2—C3	1.480 (4)	C45—H45A	0.9300
C2—H2A	0.9700	C46—H46A	0.9300
C2—H2B	0.9700	C51—C52	1.370 (4)
C4—H4A	0.9600	C51—C56	1.376 (4)
C4—H4B	0.9600	C52—C53	1.389 (4)
C4—H4C	0.9600	C52—H52A	0.9300
C11—C12	1.387 (3)	C53—C54	1.349 (4)
C11—C16	1.395 (3)	C53—H53A	0.9300
C12—C13	1.393 (3)	C54—C55	1.347 (4)
C13—C14	1.383 (3)	C54—H54A	0.9300
C14—C15	1.382 (3)	C55—C56	1.388 (4)
C14—H14A	0.9300	C55—H55A	0.9300
C15—C16	1.378 (3)	C56—H56A	0.9300
C15—H15A	0.9300	C61—C66	1.374 (4)
C16—H16A	0.9300	C61—C62	1.386 (4)
C21—C22	1.380 (3)	C62—C63	1.368 (5)
C21—C26	1.397 (3)	C62—H62A	0.9300
C22—C23	1.394 (3)	C63—C64	1.355 (5)
C23—C24	1.389 (3)	C63—H63A	0.9300
C24—C25	1.379 (4)	C64—C65	1.360 (5)
C24—H24A	0.9300	C64—H64A	0.9300
C25—C26	1.375 (3)	C65—C66	1.374 (5)
C25—H25A	0.9300	C65—H65A	0.9300
C26—H26A	0.9300	C66—H66A	0.9300
C41—P1—C31	103.40 (16)	C25—C26—C21	120.4 (3)
C41—P1—C11	101.59 (15)	C25—C26—H26A	119.8
C31—P1—C11	100.90 (13)	C21—C26—H26A	119.8
C41—P1—P2	79.67 (9)	C36—C31—C32	117.6 (3)
C31—P1—P2	160.90 (10)	C36—C31—P1	125.3 (3)
C11—P1—P2	96.84 (9)	C32—C31—P1	117.0 (3)
C61—P2—C21	100.97 (14)	C31—C32—C33	122.1 (4)
C61—P2—C51	100.55 (15)	C31—C32—H32A	119.0
C21—P2—C51	101.69 (13)	C33—C32—H32A	119.0
C61—P2—P1	71.97 (9)	C34—C33—C32	119.2 (4)
C21—P2—P1	96.74 (9)	C34—C33—H33A	120.4
C51—P2—P1	161.18 (9)	C32—C33—H33A	120.4
C13—N1—C23	119.2 (2)	C33—C34—C35	120.4 (4)
C13—N1—C1	119.3 (2)	C33—C34—H34A	119.8
C23—N1—C1	121.0 (2)	C35—C34—H34A	119.8
C12—O1—C22	119.0 (2)	C34—C35—C36	119.9 (4)
C3—O2—C4	115.3 (3)	C34—C35—H35A	120.1
C3—O3—O3'	57.4 (5)	C36—C35—H35A	120.1
C3—O3'—O3	54.6 (4)	C31—C36—C35	120.9 (3)
N1—C1—C2	113.6 (3)	C31—C36—H36A	119.5
N1—C1—H1A	108.8	C35—C36—H36A	119.5
C2—C1—H1A	108.8	C46—C41—C42	117.5 (4)
N1—C1—H1B	108.8	C46—C41—P1	117.0 (4)
C2—C1—H1B	108.8	C42—C41—P1	125.5 (3)
H1A—C1—H1B	107.7	C43—C42—C41	121.1 (3)
C3—C2—C1	111.6 (4)	C43—C42—H42A	119.4
C3—C2—H2A	109.3	C41—C42—H42A	119.4
C1—C2—H2A	109.3	C44—C43—C42	120.7 (4)
C3—C2—H2B	109.3	C44—C43—H43A	119.7
C1—C2—H2B	109.3	C42—C43—H43A	119.7
H2A—C2—H2B	108.0	C45—C44—C43	118.6 (5)
O2—C3—O3	108.5 (7)	C45—C44—H44A	120.7
O2—C3—O3'	113.6 (6)	C43—C44—H44A	120.7
O3—C3—O3'	68.1 (5)	C44—C45—C46	121.4 (5)
O2—C3—C2	117.2 (4)	C44—C45—H45A	119.3
O3—C3—C2	120.8 (6)	C46—C45—H45A	119.3
O3'—C3—C2	119.2 (6)	C45—C46—C41	120.6 (4)
O2—C4—H4A	109.5	C45—C46—H46A	119.7
O2—C4—H4B	109.5	C41—C46—H46A	119.7
H4A—C4—H4B	109.5	C52—C51—C56	116.5 (3)
O2—C4—H4C	109.5	C52—C51—P2	117.9 (3)
H4A—C4—H4C	109.5	C56—C51—P2	125.5 (3)
H4B—C4—H4C	109.5	C51—C52—C53	121.3 (4)
C12—C11—C16	117.0 (2)	C51—C52—H52A	119.3
C12—C11—P1	117.6 (2)	C53—C52—H52A	119.3
C16—C11—P1	125.3 (2)	C54—C53—C52	120.6 (4)
O1—C12—C11	115.4 (2)	C54—C53—H53A	119.7
O1—C12—C13	120.8 (2)	C52—C53—H53A	119.7
C11—C12—C13	123.7 (3)	C55—C54—C53	119.6 (4)
C14—C13—C12	117.2 (3)	C55—C54—H54A	120.2
C14—C13—N1	123.4 (3)	C53—C54—H54A	120.2
C12—C13—N1	119.4 (3)	C54—C55—C56	120.0 (4)
C15—C14—C13	120.5 (3)	C54—C55—H55A	120.0
C15—C14—H14A	119.7	C56—C55—H55A	120.0
C13—C14—H14A	119.7	C51—C56—C55	121.9 (3)
C16—C15—C14	121.1 (3)	C51—C56—H56A	119.0
C16—C15—H15A	119.5	C55—C56—H56A	119.0
C14—C15—H15A	119.5	C66—C61—C62	116.1 (3)
C15—C16—C11	120.4 (3)	C66—C61—P2	125.7 (3)
C15—C16—H16A	119.8	C62—C61—P2	118.1 (3)
C11—C16—H16A	119.8	C63—C62—C61	121.7 (4)
C22—C21—C26	116.9 (3)	C63—C62—H62A	119.1
C22—C21—P2	117.6 (2)	C61—C62—H62A	119.1
C26—C21—P2	125.5 (2)	C64—C63—C62	121.1 (5)
C21—C22—O1	115.8 (2)	C64—C63—H63A	119.5
C21—C22—C23	124.0 (3)	C62—C63—H63A	119.5
O1—C22—C23	120.2 (3)	C63—C64—C65	118.4 (5)
C24—C23—C22	117.1 (3)	C63—C64—H64A	120.8
C24—C23—N1	123.1 (3)	C65—C64—H64A	120.8
C22—C23—N1	119.7 (3)	C64—C65—C66	120.9 (4)
C25—C24—C23	120.2 (3)	C64—C65—H65A	119.6
C25—C24—H24A	119.9	C66—C65—H65A	119.6
C23—C24—H24A	119.9	C65—C66—C61	121.8 (3)
C26—C25—C24	121.3 (3)	C65—C66—H66A	119.1
C26—C25—H25A	119.3	C61—C66—H66A	119.1
C24—C25—H25A	119.3
C41—P1—P2—C61	156.93 (16)	C1—N1—C23—C24	0.4 (5)
C31—P1—P2—C61	55.8 (4)	C13—N1—C23—C22	−9.7 (4)
C11—P1—P2—C61	−102.47 (15)	C1—N1—C23—C22	178.3 (3)
C41—P1—P2—C21	−103.69 (15)	C22—C23—C24—C25	−1.0 (5)
C31—P1—P2—C21	155.2 (4)	N1—C23—C24—C25	177.0 (3)
C11—P1—P2—C21	−3.09 (14)	C23—C24—C25—C26	1.7 (5)
C41—P1—P2—C51	87.9 (4)	C24—C25—C26—C21	−0.5 (5)
C31—P1—P2—C51	−13.3 (6)	C22—C21—C26—C25	−1.3 (4)
C11—P1—P2—C51	−171.5 (4)	P2—C21—C26—C25	−178.1 (2)
C13—N1—C1—C2	−85.0 (3)	C41—P1—C31—C36	11.3 (3)
C23—N1—C1—C2	86.9 (3)	C11—P1—C31—C36	−93.5 (3)
N1—C1—C2—C3	145.9 (3)	P2—P1—C31—C36	108.5 (4)
C4—O2—C3—O3	36.1 (11)	C41—P1—C31—C32	−165.9 (2)
C4—O2—C3—O3'	−37.4 (11)	C11—P1—C31—C32	89.3 (2)
C4—O2—C3—C2	177.3 (4)	P2—P1—C31—C32	−68.7 (5)
O3'—O3—C3—O2	−108.7 (8)	C36—C31—C32—C33	1.0 (4)
O3'—O3—C3—C2	111.8 (8)	P1—C31—C32—C33	178.4 (2)
O3—O3'—C3—O2	101.4 (9)	C31—C32—C33—C34	−1.6 (5)
O3—O3'—C3—C2	−114.0 (7)	C32—C33—C34—C35	1.0 (5)
C1—C2—C3—O2	130.4 (6)	C33—C34—C35—C36	0.1 (5)
C1—C2—C3—O3	−93.4 (11)	C32—C31—C36—C35	0.2 (4)
C1—C2—C3—O3'	−12.9 (11)	P1—C31—C36—C35	−177.0 (2)
C41—P1—C11—C12	80.1 (3)	C34—C35—C36—C31	−0.8 (4)
C31—P1—C11—C12	−173.6 (3)	C31—P1—C41—C46	91.8 (2)
P2—P1—C11—C12	−0.7 (2)	C11—P1—C41—C46	−163.9 (2)
C41—P1—C11—C16	−104.4 (3)	P2—P1—C41—C46	−68.9 (2)
C31—P1—C11—C16	1.9 (3)	C31—P1—C41—C42	−88.9 (3)
P2—P1—C11—C16	174.8 (3)	C11—P1—C41—C42	15.4 (3)
C22—O1—C12—C11	170.8 (3)	P2—P1—C41—C42	110.3 (3)
C22—O1—C12—C13	−11.1 (4)	C46—C41—C42—C43	0.1 (5)
C16—C11—C12—O1	179.0 (3)	P1—C41—C42—C43	−179.1 (2)
P1—C11—C12—O1	−5.1 (4)	C41—C42—C43—C44	−0.7 (5)
C16—C11—C12—C13	1.0 (5)	C42—C43—C44—C45	0.5 (6)
P1—C11—C12—C13	176.9 (2)	C43—C44—C45—C46	0.3 (7)
O1—C12—C13—C14	−179.9 (3)	C44—C45—C46—C41	−0.9 (7)
C11—C12—C13—C14	−2.0 (5)	C42—C41—C46—C45	0.6 (5)
O1—C12—C13—N1	−0.1 (4)	P1—C41—C46—C45	180.0 (3)
C11—C12—C13—N1	177.9 (3)	C61—P2—C51—C52	−163.4 (2)
C23—N1—C13—C14	−169.7 (3)	C21—P2—C51—C52	93.0 (2)
C1—N1—C13—C14	2.5 (5)	P1—P2—C51—C52	−98.8 (4)
C23—N1—C13—C12	10.5 (4)	C61—P2—C51—C56	13.0 (3)
C1—N1—C13—C12	−177.4 (3)	C21—P2—C51—C56	−90.7 (3)
C12—C13—C14—C15	1.9 (5)	P1—P2—C51—C56	77.6 (5)
N1—C13—C14—C15	−178.0 (3)	C56—C51—C52—C53	1.5 (5)
C13—C14—C15—C16	−0.8 (5)	P2—C51—C52—C53	178.2 (2)
C14—C15—C16—C11	−0.2 (5)	C51—C52—C53—C54	−1.9 (5)
C12—C11—C16—C15	0.2 (5)	C52—C53—C54—C55	1.3 (6)
P1—C11—C16—C15	−175.4 (3)	C53—C54—C55—C56	−0.5 (6)
C61—P2—C21—C22	78.0 (3)	C52—C51—C56—C55	−0.6 (5)
C51—P2—C21—C22	−178.7 (2)	P2—C51—C56—C55	−177.1 (3)
P1—P2—C21—C22	5.1 (2)	C54—C55—C56—C51	0.1 (5)
C61—P2—C21—C26	−105.2 (3)	C21—P2—C61—C66	21.5 (3)
C51—P2—C21—C26	−1.9 (3)	C51—P2—C61—C66	−82.7 (3)
P1—P2—C21—C26	−178.1 (3)	P1—P2—C61—C66	115.1 (3)
C26—C21—C22—O1	−175.5 (2)	C21—P2—C61—C62	−161.4 (2)
P2—C21—C22—O1	1.5 (4)	C51—P2—C61—C62	94.4 (2)
C26—C21—C22—C23	2.1 (4)	P1—P2—C61—C62	−67.8 (2)
P2—C21—C22—C23	179.2 (2)	C66—C61—C62—C63	0.3 (5)
C12—O1—C22—C21	−170.4 (3)	P2—C61—C62—C63	−177.1 (3)
C12—O1—C22—C23	11.9 (4)	C61—C62—C63—C64	1.6 (7)
C21—C22—C23—C24	−1.0 (4)	C62—C63—C64—C65	−2.5 (7)
O1—C22—C23—C24	176.5 (3)	C63—C64—C65—C66	1.6 (7)
C21—C22—C23—N1	−179.0 (3)	C64—C65—C66—C61	0.3 (6)
O1—C22—C23—N1	−1.5 (4)	C62—C61—C66—C65	−1.2 (5)
C13—N1—C23—C24	172.4 (3)	P2—C61—C66—C65	176.0 (3)