Diphen­yl(1,1,3,3-tetra­methyl-2,3-dihydro-1H-isoindol-2-yl)phosphine oxide

The title compound, C₂₄H₂₆NOP, crystallizes with two independent non-chiral mol­ecules in the asymmetric unit. The mol­ecular structure consists of a tetra­hedral P atom bonded by two phenyl groups, a phosphate O atom and an isoindole group. The geometry of the two molecules is similar but not identical.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.029
• wR factor = 0.086
• Data-to-parameter ratio = 8.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.96
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.51 Ratio
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

Alert level G
REFLT03_ALERT_4_G  WARNING: Large fraction of Friedel related reflns may
                     be needed to determine absolute structure
           From the CIF: _diffrn_reflns_theta_max           25.00
           From the CIF: _reflns_number_total               3878
           Count of symmetry unique reflns         3898
           Completeness (_total/calc)             99.49%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present        yes

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

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

---

Computing details

Data collection: SDP (Frenz, 1985); cell refinement: SDP; data reduction: WinGX (Farrugia, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97; molecular graphics: PLATON98 (Spek, 1998); software used to prepare material for publication: SHELXL97.

Diphenyl(1,1,3,3-tetramethyl-2,3-dihydro-1H-isoindol-2-yl)phosphine oxide

Crystal data

C24H26NOP	F(000) = 800
Mr = 375.43	Dx = 1.212 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 25 reflections
a = 14.48 (2) Å	θ = 10.0–12.0°
b = 8.323 (1) Å	µ = 0.15 mm^−1
c = 18.455 (5) Å	T = 293 K
β = 112.280 (12)°	Prism, colourless
V = 2058 (3) Å^3	0.35 × 0.22 × 0.13 mm
Z = 4

Data collection

Enraf–Nonius CAD-4 diffractometer	3276 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.017
Graphite monochromator	θmax = 25.0°, θmin = 1.2°
w–2θ scans	h = 0→17
Absorption correction: ψ scan (North et al., 1968)	k = 0→9
Tmin = 0.950, Tmax = 0.981	l = −21→20
4422 measured reflections	3 standard reflections every 120 min
3878 independent reflections	intensity decay: 2%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.029	H-atom parameters constrained
wR(F^2) = 0.086	w = 1/[σ^2(Fo^2) + (0.0591P)^2 + 0.1682P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
3878 reflections	Δρmax = 0.18 e Å^−3
487 parameters	Δρmin = −0.18 e Å^−3
1 restraint	Absolute structure: Flack (1983), 0 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.03 (8)

Special details

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
P1A	0.47716 (4)	0.44396 (8)	0.19514 (4)	0.03662 (16)
O11A	0.52559 (14)	0.6035 (2)	0.21826 (10)	0.0498 (5)
C21A	0.48086 (18)	0.3786 (3)	0.10295 (14)	0.0412 (6)
C22A	0.39902 (19)	0.3181 (4)	0.04245 (14)	0.0481 (6)
H22A	0.3388	0.3064	0.0490	0.058*
C23A	0.4052 (2)	0.2751 (4)	−0.02729 (17)	0.0611 (8)
H23A	0.3496	0.2327	−0.0672	0.073*
C24A	0.4929 (3)	0.2943 (4)	−0.03864 (18)	0.0692 (9)
H24A	0.4970	0.2648	−0.0859	0.083*
C25A	0.5752 (3)	0.3580 (4)	0.0209 (2)	0.0675 (9)
H25A	0.6347	0.3724	0.0135	0.081*
C26A	0.5692 (2)	0.4001 (4)	0.09115 (17)	0.0536 (7)
H26A	0.6247	0.4433	0.1309	0.064*
C31A	0.34494 (17)	0.4648 (3)	0.17719 (13)	0.0407 (6)
C32A	0.29360 (19)	0.3632 (4)	0.20845 (15)	0.0490 (6)
H32A	0.3264	0.2774	0.2400	0.059*
C33A	0.1921 (2)	0.3901 (4)	0.19238 (18)	0.0602 (8)
H33A	0.1578	0.3225	0.2136	0.072*
C34A	0.1435 (2)	0.5154 (5)	0.14556 (17)	0.0643 (9)
H34A	0.0760	0.5322	0.1345	0.077*
C35A	0.1939 (2)	0.6161 (5)	0.11497 (17)	0.0632 (8)
H35A	0.1608	0.7017	0.0834	0.076*
C36A	0.2934 (2)	0.5912 (4)	0.13065 (16)	0.0542 (7)
H36A	0.3268	0.6608	0.1095	0.065*
N41A	0.52855 (14)	0.3034 (3)	0.26138 (11)	0.0367 (5)
C42A	0.54270 (19)	0.1266 (3)	0.24875 (14)	0.0397 (6)
C43A	0.57909 (18)	0.0652 (3)	0.33186 (14)	0.0396 (6)
C44A	0.59499 (18)	0.1869 (3)	0.38534 (14)	0.0402 (6)
C45A	0.57628 (18)	0.3497 (3)	0.34657 (13)	0.0396 (6)
C46A	0.5978 (2)	−0.0943 (3)	0.35569 (16)	0.0482 (7)
H46A	0.5878	−0.1767	0.3194	0.058*
C47A	0.6321 (2)	−0.1264 (4)	0.43554 (17)	0.0577 (7)
H47A	0.6453	−0.2319	0.4529	0.069*
C48A	0.6465 (2)	−0.0056 (4)	0.48888 (16)	0.0584 (8)
H48A	0.6684	−0.0301	0.5419	0.070*
C49A	0.6289 (2)	0.1537 (4)	0.46471 (15)	0.0509 (7)
H49A	0.6397	0.2360	0.5011	0.061*
C50A	0.6223 (2)	0.0950 (4)	0.21443 (15)	0.0548 (7)
H50A	0.6784	0.1645	0.2391	0.082*
H50B	0.5947	0.1157	0.1591	0.082*
H50C	0.6436	−0.0149	0.2235	0.082*
C51A	0.4457 (2)	0.0398 (4)	0.19859 (15)	0.0526 (7)
H51A	0.4569	−0.0742	0.2017	0.079*
H51B	0.4254	0.0740	0.1451	0.079*
H51C	0.3943	0.0653	0.2177	0.079*
C52A	0.67623 (19)	0.4370 (4)	0.36442 (15)	0.0527 (7)
H52A	0.7094	0.4506	0.4200	0.079*
H52B	0.6640	0.5404	0.3395	0.079*
H52C	0.7176	0.3746	0.3449	0.079*
C53A	0.5073 (2)	0.4516 (4)	0.37355 (15)	0.0524 (7)
H53A	0.4436	0.3996	0.3588	0.079*
H53B	0.4987	0.5555	0.3494	0.079*
H53C	0.5363	0.4635	0.4294	0.079*
P1B	0.01406 (5)	1.00991 (9)	0.29341 (4)	0.04392 (19)
O11B	−0.01389 (17)	1.1774 (3)	0.26549 (13)	0.0671 (6)
C21B	−0.01243 (18)	0.9717 (4)	0.37954 (15)	0.0496 (7)
C22B	0.0535 (2)	0.9077 (4)	0.44804 (16)	0.0603 (8)
H22B	0.1170	0.8770	0.4521	0.072*
C23B	0.0249 (3)	0.8888 (6)	0.5116 (2)	0.0867 (12)
H23B	0.0689	0.8449	0.5582	0.104*
C24B	−0.0696 (3)	0.9359 (6)	0.5046 (3)	0.0948 (15)
H24B	−0.0899	0.9200	0.5462	0.114*
C25B	−0.1332 (3)	1.0051 (7)	0.4375 (2)	0.0965 (15)
H25B	−0.1958	1.0400	0.4340	0.116*
C26B	−0.1051 (2)	1.0233 (5)	0.3758 (2)	0.0760 (11)
H26B	−0.1488	1.0711	0.3301	0.091*
C31B	0.14753 (19)	0.9852 (4)	0.32181 (14)	0.0460 (7)
C32B	0.1901 (2)	0.8654 (4)	0.29269 (17)	0.0571 (7)
H32B	0.1494	0.7905	0.2576	0.069*
C33B	0.2926 (2)	0.8561 (5)	0.31540 (19)	0.0696 (9)
H33B	0.3203	0.7752	0.2953	0.084*
C34B	0.3533 (2)	0.9640 (6)	0.36684 (17)	0.0700 (10)
H34B	0.4222	0.9562	0.3823	0.084*
C35B	0.3129 (2)	1.0830 (6)	0.39548 (18)	0.0737 (10)
H35B	0.3543	1.1574	0.4304	0.088*
C36B	0.2109 (2)	1.0948 (5)	0.37334 (17)	0.0623 (8)
H36B	0.1842	1.1775	0.3933	0.075*
N41B	−0.04657 (15)	0.8747 (3)	0.22612 (11)	0.0402 (5)
C42B	−0.0764 (2)	0.7055 (3)	0.23777 (14)	0.0449 (6)
C43B	−0.10355 (18)	0.6388 (3)	0.15585 (14)	0.0398 (6)
C44B	−0.10735 (17)	0.7567 (3)	0.10293 (14)	0.0384 (5)
C45B	−0.08391 (18)	0.9210 (3)	0.14081 (14)	0.0411 (6)
C46B	−0.1242 (2)	0.4807 (3)	0.13235 (16)	0.0510 (7)
H46B	−0.1207	0.4006	0.1684	0.061*
C47B	−0.1501 (2)	0.4444 (4)	0.05381 (17)	0.0574 (7)
H47B	−0.1651	0.3388	0.0369	0.069*
C48B	−0.1540 (2)	0.5620 (4)	0.00069 (16)	0.0555 (7)
H48B	−0.1710	0.5353	−0.0517	0.067*
C49B	−0.13275 (19)	0.7204 (4)	0.02440 (15)	0.0470 (6)
H49B	−0.1355	0.8004	−0.0115	0.056*
C50B	−0.1692 (3)	0.7004 (4)	0.25883 (18)	0.0674 (9)
H50D	−0.1515	0.7333	0.3123	0.101*
H50E	−0.1952	0.5929	0.2523	0.101*
H50F	−0.2191	0.7718	0.2250	0.101*
C51B	0.0074 (3)	0.6079 (4)	0.29660 (16)	0.0696 (10)
H51D	0.0627	0.6025	0.2800	0.104*
H51E	−0.0160	0.5013	0.2998	0.104*
H51F	0.0285	0.6583	0.3471	0.104*
C52B	−0.1789 (2)	1.0219 (4)	0.11769 (16)	0.0536 (7)
H52D	−0.2267	0.9677	0.1335	0.080*
H52E	−0.2063	1.0369	0.0620	0.080*
H52F	−0.1633	1.1247	0.1431	0.080*
C53B	−0.0054 (2)	1.0071 (4)	0.11850 (16)	0.0583 (8)
H53D	0.0064	1.1122	0.1416	0.088*
H53E	−0.0289	1.0167	0.0626	0.088*
H53F	0.0556	0.9466	0.1373	0.088*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1A	0.0398 (3)	0.0314 (4)	0.0375 (3)	0.0004 (3)	0.0134 (2)	0.0001 (3)
O11A	0.0582 (11)	0.0354 (11)	0.0498 (11)	−0.0058 (9)	0.0136 (9)	−0.0001 (9)
C21A	0.0464 (13)	0.0375 (14)	0.0398 (12)	0.0056 (11)	0.0167 (10)	0.0063 (11)
C22A	0.0481 (13)	0.0499 (16)	0.0426 (13)	0.0079 (13)	0.0129 (11)	−0.0017 (13)
C23A	0.076 (2)	0.056 (2)	0.0435 (14)	0.0151 (16)	0.0139 (13)	−0.0034 (14)
C24A	0.113 (3)	0.0510 (19)	0.0558 (17)	0.018 (2)	0.0462 (19)	0.0054 (16)
C25A	0.086 (2)	0.058 (2)	0.082 (2)	0.0017 (19)	0.058 (2)	0.0045 (19)
C26A	0.0568 (16)	0.0485 (18)	0.0616 (16)	−0.0032 (14)	0.0293 (13)	0.0019 (14)
C31A	0.0438 (12)	0.0381 (16)	0.0402 (11)	0.0065 (12)	0.0159 (10)	−0.0025 (12)
C32A	0.0465 (14)	0.0481 (17)	0.0542 (14)	0.0038 (13)	0.0212 (12)	−0.0005 (14)
C33A	0.0499 (16)	0.068 (2)	0.0677 (18)	−0.0049 (15)	0.0279 (14)	−0.0085 (17)
C34A	0.0452 (15)	0.084 (3)	0.0618 (17)	0.0167 (17)	0.0176 (13)	−0.0132 (19)
C35A	0.0625 (18)	0.068 (2)	0.0555 (16)	0.0266 (17)	0.0181 (14)	0.0035 (16)
C36A	0.0596 (16)	0.0512 (19)	0.0545 (16)	0.0148 (15)	0.0248 (13)	0.0075 (14)
N41A	0.0413 (10)	0.0325 (12)	0.0346 (10)	0.0040 (9)	0.0126 (8)	−0.0007 (9)
C42A	0.0500 (14)	0.0304 (13)	0.0375 (12)	0.0060 (11)	0.0152 (11)	−0.0012 (11)
C43A	0.0405 (12)	0.0370 (14)	0.0431 (13)	0.0016 (11)	0.0181 (10)	0.0018 (11)
C44A	0.0411 (13)	0.0411 (15)	0.0401 (13)	0.0024 (11)	0.0174 (10)	−0.0006 (11)
C45A	0.0448 (13)	0.0379 (15)	0.0337 (12)	0.0019 (11)	0.0123 (10)	−0.0044 (11)
C46A	0.0619 (16)	0.0325 (16)	0.0495 (15)	0.0039 (12)	0.0204 (13)	0.0041 (12)
C47A	0.0699 (18)	0.0468 (17)	0.0572 (17)	0.0077 (15)	0.0250 (14)	0.0147 (15)
C48A	0.0701 (18)	0.065 (2)	0.0410 (14)	0.0057 (16)	0.0216 (13)	0.0149 (15)
C49A	0.0630 (17)	0.0480 (18)	0.0417 (14)	0.0027 (14)	0.0198 (13)	−0.0022 (13)
C50A	0.0683 (17)	0.0521 (18)	0.0519 (15)	0.0195 (15)	0.0316 (14)	0.0060 (14)
C51A	0.0672 (17)	0.0354 (16)	0.0471 (14)	−0.0026 (14)	0.0124 (12)	−0.0034 (12)
C52A	0.0489 (14)	0.0505 (17)	0.0493 (14)	−0.0061 (15)	0.0080 (11)	−0.0020 (14)
C53A	0.0628 (16)	0.0477 (17)	0.0470 (13)	0.0055 (16)	0.0211 (12)	−0.0107 (14)
P1B	0.0473 (4)	0.0354 (4)	0.0431 (3)	−0.0006 (3)	0.0103 (3)	−0.0051 (3)
O11B	0.0772 (14)	0.0354 (12)	0.0679 (14)	−0.0005 (11)	0.0042 (11)	−0.0049 (11)
C21B	0.0448 (13)	0.0540 (18)	0.0495 (13)	−0.0064 (13)	0.0172 (11)	−0.0147 (13)
C22B	0.0657 (17)	0.065 (2)	0.0487 (15)	−0.0002 (16)	0.0204 (13)	−0.0027 (15)
C23B	0.113 (3)	0.091 (3)	0.0551 (19)	−0.012 (3)	0.031 (2)	−0.005 (2)
C24B	0.112 (3)	0.109 (4)	0.094 (3)	−0.043 (3)	0.074 (3)	−0.036 (3)
C25B	0.071 (2)	0.132 (4)	0.101 (3)	−0.024 (3)	0.050 (2)	−0.052 (3)
C26B	0.0518 (16)	0.098 (3)	0.074 (2)	−0.0015 (19)	0.0192 (15)	−0.034 (2)
C31B	0.0487 (13)	0.0491 (18)	0.0417 (12)	−0.0083 (13)	0.0189 (11)	−0.0047 (12)
C32B	0.0525 (16)	0.0581 (19)	0.0578 (16)	−0.0050 (14)	0.0176 (13)	−0.0145 (15)
C33B	0.0588 (18)	0.080 (3)	0.073 (2)	0.0097 (18)	0.0293 (15)	−0.0058 (19)
C34B	0.0474 (15)	0.108 (3)	0.0571 (16)	−0.013 (2)	0.0223 (13)	−0.002 (2)
C35B	0.0615 (18)	0.102 (3)	0.0610 (18)	−0.033 (2)	0.0264 (15)	−0.023 (2)
C36B	0.0613 (17)	0.066 (2)	0.0645 (18)	−0.0172 (16)	0.0296 (15)	−0.0212 (17)
N41B	0.0480 (11)	0.0323 (11)	0.0356 (10)	−0.0048 (10)	0.0107 (9)	−0.0003 (9)
C42B	0.0607 (16)	0.0342 (15)	0.0390 (13)	−0.0072 (13)	0.0181 (12)	−0.0009 (11)
C43B	0.0429 (13)	0.0338 (14)	0.0424 (13)	−0.0015 (11)	0.0159 (11)	−0.0006 (11)
C44B	0.0380 (12)	0.0338 (13)	0.0415 (12)	−0.0003 (10)	0.0130 (10)	0.0011 (11)
C45B	0.0468 (13)	0.0343 (15)	0.0380 (12)	−0.0064 (11)	0.0114 (10)	0.0020 (11)
C46B	0.0683 (17)	0.0322 (16)	0.0538 (15)	−0.0050 (13)	0.0245 (13)	−0.0027 (12)
C47B	0.0718 (18)	0.0392 (16)	0.0607 (17)	−0.0023 (15)	0.0244 (14)	−0.0116 (15)
C48B	0.0652 (17)	0.0567 (19)	0.0436 (14)	0.0029 (15)	0.0196 (13)	−0.0107 (14)
C49B	0.0524 (15)	0.0457 (17)	0.0410 (13)	0.0048 (13)	0.0156 (11)	0.0042 (12)
C50B	0.093 (2)	0.062 (2)	0.0648 (18)	−0.0261 (19)	0.0490 (17)	−0.0143 (17)
C51B	0.103 (3)	0.0409 (18)	0.0446 (16)	−0.0036 (17)	0.0050 (16)	0.0092 (14)
C52B	0.0584 (16)	0.0367 (16)	0.0544 (15)	0.0032 (14)	0.0086 (13)	−0.0010 (14)
C53B	0.0661 (17)	0.0531 (19)	0.0535 (15)	−0.0144 (16)	0.0201 (13)	0.0103 (15)

Geometric parameters (Å, º)

P1A—O11A	1.487 (2)	P1B—O11B	1.488 (2)
P1A—N41A	1.651 (2)	P1B—N41B	1.659 (2)
P1A—C21A	1.806 (3)	P1B—C21B	1.799 (3)
P1A—C31A	1.823 (2)	P1B—C31B	1.812 (3)
C21A—C22A	1.378 (4)	C21B—C22B	1.370 (4)
C21A—C26A	1.388 (4)	C21B—C26B	1.385 (4)
C22A—C23A	1.371 (4)	C22B—C23B	1.392 (5)
C22A—H22A	0.9300	C22B—H22B	0.9300
C23A—C24A	1.372 (5)	C23B—C24B	1.380 (6)
C23A—H23A	0.9300	C23B—H23B	0.9300
C24A—C25A	1.384 (5)	C24B—C25B	1.360 (6)
C24A—H24A	0.9300	C24B—H24B	0.9300
C25A—C26A	1.377 (4)	C25B—C26B	1.355 (5)
C25A—H25A	0.9300	C25B—H25B	0.9300
C26A—H26A	0.9300	C26B—H26B	0.9300
C31A—C36A	1.384 (4)	C31B—C32B	1.383 (4)
C31A—C32A	1.388 (4)	C31B—C36B	1.384 (4)
C32A—C33A	1.403 (4)	C32B—C33B	1.384 (4)
C32A—H32A	0.9300	C32B—H32B	0.9300
C33A—C34A	1.367 (5)	C33B—C34B	1.359 (5)
C33A—H33A	0.9300	C33B—H33B	0.9300
C34A—C35A	1.366 (5)	C34B—C35B	1.356 (6)
C34A—H34A	0.9300	C34B—H34B	0.9300
C35A—C36A	1.372 (4)	C35B—C36B	1.378 (4)
C35A—H35A	0.9300	C35B—H35B	0.9300
C36A—H36A	0.9300	C36B—H36B	0.9300
N41A—C45A	1.508 (3)	N41B—C45B	1.508 (3)
N41A—C42A	1.516 (3)	N41B—C42B	1.511 (3)
C42A—C43A	1.509 (3)	C42B—C43B	1.516 (3)
C42A—C50A	1.533 (3)	C42B—C51B	1.520 (4)
C42A—C51A	1.538 (4)	C42B—C50B	1.535 (4)
C43A—C44A	1.371 (4)	C43B—C44B	1.371 (4)
C43A—C46A	1.393 (4)	C43B—C46B	1.382 (4)
C44A—C49A	1.385 (4)	C44B—C49B	1.387 (3)
C44A—C45A	1.508 (4)	C44B—C45B	1.514 (4)
C45A—C53A	1.530 (4)	C45B—C53B	1.526 (4)
C45A—C52A	1.539 (4)	C45B—C52B	1.527 (4)
C46A—C47A	1.391 (4)	C46B—C47B	1.386 (4)
C46A—H46A	0.9300	C46B—H46B	0.9300
C47A—C48A	1.367 (5)	C47B—C48B	1.372 (4)
C47A—H47A	0.9300	C47B—H47B	0.9300
C48A—C49A	1.391 (5)	C48B—C49B	1.386 (4)
C48A—H48A	0.9300	C48B—H48B	0.9300
C49A—H49A	0.9300	C49B—H49B	0.9300
C50A—H50A	0.9600	C50B—H50D	0.9600
C50A—H50B	0.9600	C50B—H50E	0.9600
C50A—H50C	0.9600	C50B—H50F	0.9600
C51A—H51A	0.9600	C51B—H51D	0.9600
C51A—H51B	0.9600	C51B—H51E	0.9600
C51A—H51C	0.9600	C51B—H51F	0.9600
C52A—H52A	0.9600	C52B—H52D	0.9600
C52A—H52B	0.9600	C52B—H52E	0.9600
C52A—H52C	0.9600	C52B—H52F	0.9600
C53A—H53A	0.9600	C53B—H53D	0.9600
C53A—H53B	0.9600	C53B—H53E	0.9600
C53A—H53C	0.9600	C53B—H53F	0.9600
O11A—P1A—N41A	112.90 (10)	O11B—P1B—N41B	112.28 (12)
O11A—P1A—C21A	111.13 (12)	O11B—P1B—C21B	110.53 (14)
N41A—P1A—C21A	108.54 (11)	N41B—P1B—C21B	108.16 (12)
O11A—P1A—C31A	108.39 (12)	O11B—P1B—C31B	109.06 (14)
N41A—P1A—C31A	110.44 (11)	N41B—P1B—C31B	110.05 (12)
C21A—P1A—C31A	105.16 (11)	C21B—P1B—C31B	106.59 (12)
C22A—C21A—C26A	118.7 (2)	C22B—C21B—C26B	119.3 (3)
C22A—C21A—P1A	123.3 (2)	C22B—C21B—P1B	125.2 (2)
C26A—C21A—P1A	117.8 (2)	C26B—C21B—P1B	115.3 (2)
C23A—C22A—C21A	120.9 (3)	C21B—C22B—C23B	119.7 (3)
C23A—C22A—H22A	119.5	C21B—C22B—H22B	120.1
C21A—C22A—H22A	119.5	C23B—C22B—H22B	120.1
C22A—C23A—C24A	120.4 (3)	C24B—C23B—C22B	119.3 (4)
C22A—C23A—H23A	119.8	C24B—C23B—H23B	120.4
C24A—C23A—H23A	119.8	C22B—C23B—H23B	120.4
C23A—C24A—C25A	119.4 (3)	C25B—C24B—C23B	120.7 (3)
C23A—C24A—H24A	120.3	C25B—C24B—H24B	119.7
C25A—C24A—H24A	120.3	C23B—C24B—H24B	119.7
C26A—C25A—C24A	120.2 (3)	C26B—C25B—C24B	119.8 (4)
C26A—C25A—H25A	119.9	C26B—C25B—H25B	120.1
C24A—C25A—H25A	119.9	C24B—C25B—H25B	120.1
C25A—C26A—C21A	120.4 (3)	C25B—C26B—C21B	121.1 (4)
C25A—C26A—H26A	119.8	C25B—C26B—H26B	119.5
C21A—C26A—H26A	119.8	C21B—C26B—H26B	119.5
C36A—C31A—C32A	118.2 (2)	C32B—C31B—C36B	117.7 (3)
C36A—C31A—P1A	117.9 (2)	C32B—C31B—P1B	123.5 (2)
C32A—C31A—P1A	123.9 (2)	C36B—C31B—P1B	118.7 (2)
C31A—C32A—C33A	119.9 (3)	C31B—C32B—C33B	120.5 (3)
C31A—C32A—H32A	120.1	C31B—C32B—H32B	119.8
C33A—C32A—H32A	120.1	C33B—C32B—H32B	119.8
C34A—C33A—C32A	120.1 (3)	C34B—C33B—C32B	120.6 (3)
C34A—C33A—H33A	119.9	C34B—C33B—H33B	119.7
C32A—C33A—H33A	119.9	C32B—C33B—H33B	119.7
C35A—C34A—C33A	120.1 (3)	C33B—C34B—C35B	119.7 (3)
C35A—C34A—H34A	119.9	C33B—C34B—H34B	120.2
C33A—C34A—H34A	119.9	C35B—C34B—H34B	120.2
C34A—C35A—C36A	120.2 (3)	C34B—C35B—C36B	120.6 (3)
C34A—C35A—H35A	119.9	C34B—C35B—H35B	119.7
C36A—C35A—H35A	119.9	C36B—C35B—H35B	119.7
C35A—C36A—C31A	121.5 (3)	C35B—C36B—C31B	120.9 (3)
C35A—C36A—H36A	119.3	C35B—C36B—H36B	119.6
C31A—C36A—H36A	119.3	C31B—C36B—H36B	119.6
C45A—N41A—C42A	111.89 (19)	C45B—N41B—C42B	112.20 (19)
C45A—N41A—P1A	119.40 (17)	C45B—N41B—P1B	119.11 (17)
C42A—N41A—P1A	128.54 (16)	C42B—N41B—P1B	128.61 (17)
C43A—C42A—N41A	100.82 (19)	N41B—C42B—C43B	100.33 (19)
C43A—C42A—C50A	109.5 (2)	N41B—C42B—C51B	113.9 (2)
N41A—C42A—C50A	113.3 (2)	C43B—C42B—C51B	110.6 (2)
C43A—C42A—C51A	109.9 (2)	N41B—C42B—C50B	112.7 (2)
N41A—C42A—C51A	113.8 (2)	C43B—C42B—C50B	108.7 (2)
C50A—C42A—C51A	109.2 (2)	C51B—C42B—C50B	110.0 (2)
C44A—C43A—C46A	121.1 (2)	C44B—C43B—C46B	120.8 (2)
C44A—C43A—C42A	112.3 (2)	C44B—C43B—C42B	111.9 (2)
C46A—C43A—C42A	126.5 (2)	C46B—C43B—C42B	127.2 (2)
C43A—C44A—C49A	120.6 (3)	C43B—C44B—C49B	120.8 (2)
C43A—C44A—C45A	111.8 (2)	C43B—C44B—C45B	112.1 (2)
C49A—C44A—C45A	127.5 (2)	C49B—C44B—C45B	127.1 (2)
N41A—C45A—C44A	101.2 (2)	N41B—C45B—C44B	100.38 (19)
N41A—C45A—C53A	112.5 (2)	N41B—C45B—C53B	113.1 (2)
C44A—C45A—C53A	111.4 (2)	C44B—C45B—C53B	111.0 (2)
N41A—C45A—C52A	111.4 (2)	N41B—C45B—C52B	111.1 (2)
C44A—C45A—C52A	109.7 (2)	C44B—C45B—C52B	110.3 (2)
C53A—C45A—C52A	110.2 (2)	C53B—C45B—C52B	110.4 (2)
C47A—C46A—C43A	117.8 (3)	C43B—C46B—C47B	118.5 (3)
C47A—C46A—H46A	121.1	C43B—C46B—H46B	120.8
C43A—C46A—H46A	121.1	C47B—C46B—H46B	120.8
C48A—C47A—C46A	121.2 (3)	C48B—C47B—C46B	120.9 (3)
C48A—C47A—H47A	119.4	C48B—C47B—H47B	119.6
C46A—C47A—H47A	119.4	C46B—C47B—H47B	119.6
C47A—C48A—C49A	120.7 (3)	C47B—C48B—C49B	120.6 (3)
C47A—C48A—H48A	119.6	C47B—C48B—H48B	119.7
C49A—C48A—H48A	119.6	C49B—C48B—H48B	119.7
C44A—C49A—C48A	118.5 (3)	C48B—C49B—C44B	118.5 (3)
C44A—C49A—H49A	120.7	C48B—C49B—H49B	120.8
C48A—C49A—H49A	120.7	C44B—C49B—H49B	120.8
C42A—C50A—H50A	109.5	C42B—C50B—H50D	109.5
C42A—C50A—H50B	109.5	C42B—C50B—H50E	109.5
H50A—C50A—H50B	109.5	H50D—C50B—H50E	109.5
C42A—C50A—H50C	109.5	C42B—C50B—H50F	109.5
H50A—C50A—H50C	109.5	H50D—C50B—H50F	109.5
H50B—C50A—H50C	109.5	H50E—C50B—H50F	109.5
C42A—C51A—H51A	109.5	C42B—C51B—H51D	109.5
C42A—C51A—H51B	109.5	C42B—C51B—H51E	109.5
H51A—C51A—H51B	109.5	H51D—C51B—H51E	109.5
C42A—C51A—H51C	109.5	C42B—C51B—H51F	109.5
H51A—C51A—H51C	109.5	H51D—C51B—H51F	109.5
H51B—C51A—H51C	109.5	H51E—C51B—H51F	109.5
C45A—C52A—H52A	109.5	C45B—C52B—H52D	109.5
C45A—C52A—H52B	109.5	C45B—C52B—H52E	109.5
H52A—C52A—H52B	109.5	H52D—C52B—H52E	109.5
C45A—C52A—H52C	109.5	C45B—C52B—H52F	109.5
H52A—C52A—H52C	109.5	H52D—C52B—H52F	109.5
H52B—C52A—H52C	109.5	H52E—C52B—H52F	109.5
C45A—C53A—H53A	109.5	C45B—C53B—H53D	109.5
C45A—C53A—H53B	109.5	C45B—C53B—H53E	109.5
H53A—C53A—H53B	109.5	H53D—C53B—H53E	109.5
C45A—C53A—H53C	109.5	C45B—C53B—H53F	109.5
H53A—C53A—H53C	109.5	H53D—C53B—H53F	109.5
H53B—C53A—H53C	109.5	H53E—C53B—H53F	109.5
O11A—P1A—C21A—C22A	−132.6 (2)	O11B—P1B—C21B—C22B	−129.3 (3)
N41A—P1A—C21A—C22A	102.7 (2)	N41B—P1B—C21B—C22B	107.4 (3)
C31A—P1A—C21A—C22A	−15.5 (3)	C31B—P1B—C21B—C22B	−10.9 (3)
O11A—P1A—C21A—C26A	43.2 (3)	O11B—P1B—C21B—C26B	45.9 (3)
N41A—P1A—C21A—C26A	−81.5 (2)	N41B—P1B—C21B—C26B	−77.4 (3)
C31A—P1A—C21A—C26A	160.3 (2)	C31B—P1B—C21B—C26B	164.3 (3)
C26A—C21A—C22A—C23A	2.1 (4)	C26B—C21B—C22B—C23B	2.9 (5)
P1A—C21A—C22A—C23A	177.8 (2)	P1B—C21B—C22B—C23B	177.9 (3)
C21A—C22A—C23A—C24A	−1.2 (5)	C21B—C22B—C23B—C24B	−0.4 (6)
C22A—C23A—C24A—C25A	−0.2 (5)	C22B—C23B—C24B—C25B	−2.3 (7)
C23A—C24A—C25A—C26A	0.7 (5)	C23B—C24B—C25B—C26B	2.3 (7)
C24A—C25A—C26A—C21A	0.2 (5)	C24B—C25B—C26B—C21B	0.3 (7)
C22A—C21A—C26A—C25A	−1.6 (4)	C22B—C21B—C26B—C25B	−2.9 (6)
P1A—C21A—C26A—C25A	−177.6 (2)	P1B—C21B—C26B—C25B	−178.4 (3)
O11A—P1A—C31A—C36A	47.8 (2)	O11B—P1B—C31B—C32B	−126.0 (3)
N41A—P1A—C31A—C36A	171.97 (19)	N41B—P1B—C31B—C32B	−2.4 (3)
C21A—P1A—C31A—C36A	−71.1 (2)	C21B—P1B—C31B—C32B	114.7 (3)
O11A—P1A—C31A—C32A	−131.1 (2)	O11B—P1B—C31B—C36B	51.7 (3)
N41A—P1A—C31A—C32A	−6.9 (3)	N41B—P1B—C31B—C36B	175.3 (2)
C21A—P1A—C31A—C32A	110.0 (2)	C21B—P1B—C31B—C36B	−67.7 (3)
C36A—C31A—C32A—C33A	0.1 (4)	C36B—C31B—C32B—C33B	0.6 (5)
P1A—C31A—C32A—C33A	179.0 (2)	P1B—C31B—C32B—C33B	178.3 (3)
C31A—C32A—C33A—C34A	0.5 (4)	C31B—C32B—C33B—C34B	0.2 (5)
C32A—C33A—C34A—C35A	−0.7 (5)	C32B—C33B—C34B—C35B	−0.8 (5)
C33A—C34A—C35A—C36A	0.4 (5)	C33B—C34B—C35B—C36B	0.5 (5)
C34A—C35A—C36A—C31A	0.1 (5)	C34B—C35B—C36B—C31B	0.4 (5)
C32A—C31A—C36A—C35A	−0.4 (4)	C32B—C31B—C36B—C35B	−0.9 (5)
P1A—C31A—C36A—C35A	−179.4 (2)	P1B—C31B—C36B—C35B	−178.7 (3)
O11A—P1A—N41A—C45A	29.5 (2)	O11B—P1B—N41B—C45B	25.7 (2)
C21A—P1A—N41A—C45A	153.22 (17)	C21B—P1B—N41B—C45B	147.97 (19)
C31A—P1A—N41A—C45A	−91.98 (19)	C31B—P1B—N41B—C45B	−95.9 (2)
O11A—P1A—N41A—C42A	−145.3 (2)	O11B—P1B—N41B—C42B	−150.7 (2)
C21A—P1A—N41A—C42A	−21.6 (2)	C21B—P1B—N41B—C42B	−28.4 (2)
C31A—P1A—N41A—C42A	93.2 (2)	C31B—P1B—N41B—C42B	87.6 (2)
C45A—N41A—C42A—C43A	12.9 (3)	C45B—N41B—C42B—C43B	17.2 (3)
P1A—N41A—C42A—C43A	−172.00 (16)	P1B—N41B—C42B—C43B	−166.21 (18)
C45A—N41A—C42A—C50A	−104.1 (2)	C45B—N41B—C42B—C51B	135.3 (2)
P1A—N41A—C42A—C50A	71.0 (3)	P1B—N41B—C42B—C51B	−48.0 (3)
C45A—N41A—C42A—C51A	130.4 (2)	C45B—N41B—C42B—C50B	−98.3 (2)
P1A—N41A—C42A—C51A	−54.5 (3)	P1B—N41B—C42B—C50B	78.3 (3)
N41A—C42A—C43A—C44A	−6.1 (3)	N41B—C42B—C43B—C44B	−10.0 (3)
C50A—C42A—C43A—C44A	113.6 (3)	C51B—C42B—C43B—C44B	−130.6 (3)
C51A—C42A—C43A—C44A	−126.5 (2)	C50B—C42B—C43B—C44B	108.4 (3)
N41A—C42A—C43A—C46A	175.1 (3)	N41B—C42B—C43B—C46B	170.7 (3)
C50A—C42A—C43A—C46A	−65.1 (4)	C51B—C42B—C43B—C46B	50.1 (4)
C51A—C42A—C43A—C46A	54.8 (3)	C50B—C42B—C43B—C46B	−70.9 (4)
C46A—C43A—C44A—C49A	−0.9 (4)	C46B—C43B—C44B—C49B	0.5 (4)
C42A—C43A—C44A—C49A	−179.8 (2)	C42B—C43B—C44B—C49B	−178.8 (2)
C46A—C43A—C44A—C45A	176.2 (2)	C46B—C43B—C44B—C45B	179.1 (2)
C42A—C43A—C44A—C45A	−2.7 (3)	C42B—C43B—C44B—C45B	−0.3 (3)
C42A—N41A—C45A—C44A	−14.3 (2)	C42B—N41B—C45B—C44B	−17.3 (3)
P1A—N41A—C45A—C44A	170.07 (16)	P1B—N41B—C45B—C44B	165.70 (16)
C42A—N41A—C45A—C53A	−133.3 (2)	C42B—N41B—C45B—C53B	−135.7 (2)
P1A—N41A—C45A—C53A	51.0 (3)	P1B—N41B—C45B—C53B	47.3 (3)
C42A—N41A—C45A—C52A	102.3 (3)	C42B—N41B—C45B—C52B	99.4 (3)
P1A—N41A—C45A—C52A	−73.3 (2)	P1B—N41B—C45B—C52B	−77.6 (2)
C43A—C44A—C45A—N41A	10.2 (3)	C43B—C44B—C45B—N41B	10.5 (3)
C49A—C44A—C45A—N41A	−173.0 (2)	C49B—C44B—C45B—N41B	−171.1 (2)
C43A—C44A—C45A—C53A	130.0 (2)	C43B—C44B—C45B—C53B	130.4 (2)
C49A—C44A—C45A—C53A	−53.2 (3)	C49B—C44B—C45B—C53B	−51.2 (3)
C43A—C44A—C45A—C52A	−107.7 (2)	C43B—C44B—C45B—C52B	−106.8 (2)
C49A—C44A—C45A—C52A	69.2 (3)	C49B—C44B—C45B—C52B	71.6 (3)
C44A—C43A—C46A—C47A	0.8 (4)	C44B—C43B—C46B—C47B	−0.9 (4)
C42A—C43A—C46A—C47A	179.4 (2)	C42B—C43B—C46B—C47B	178.4 (3)
C43A—C46A—C47A—C48A	0.2 (5)	C43B—C46B—C47B—C48B	0.9 (4)
C46A—C47A—C48A—C49A	−1.1 (5)	C46B—C47B—C48B—C49B	−0.5 (5)
C43A—C44A—C49A—C48A	0.0 (4)	C47B—C48B—C49B—C44B	0.1 (4)
C45A—C44A—C49A—C48A	−176.5 (3)	C43B—C44B—C49B—C48B	−0.1 (4)
C47A—C48A—C49A—C44A	0.9 (5)	C45B—C44B—C49B—C48B	−178.4 (3)