A monomeric N,N′-dilithio­bis(amido)organophosphane

The title compound [μ₂-bis­(2,6-diisopropyl­phenyl­amido)phenyl­phospaine]bis­(diethyl ether)dilithium(I), [Li₂(C₃₀H₃₉N₂P)(C₄H₁₀O)₂] or Li₂(Et₂O)₂[PhP(NDipp)₂] (Dipp = 2,6-diisopropyl­phen­yl), has been structurally characterized. This is the first example of a monomeric N,N′-dilithio­bis(amido)organophosphane. The steric con­straints of the bulky diisopropyl­phenyl substituents bonded to the N atom and the solvation of the lithium ions by a donor solvent prevent the formation of a higher oligomer.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.050
• wR factor = 0.123
• Data-to-parameter ratio = 16.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.96 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.28 Ratio

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

   1 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
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

[µ₂-bis(2,6-diisopropylphenylamido)phenylphosphine]bis(diethyl ether)dilithium(I)

Crystal data

[Li2(C30H39N2P)(C4H10O)2]	F(000) = 1352
Mr = 620.72	Dx = 1.086 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 12831 reflections
a = 15.679 (3) Å	θ = 3.0–27.5°
b = 15.381 (3) Å	µ = 0.11 mm^−1
c = 16.734 (3) Å	T = 173 K
β = 109.78 (3)°	Block, yellow
V = 3797.7 (13) Å^3	0.30 × 0.20 × 0.10 mm
Z = 4

Data collection

Nonius KappaCCD diffractometer	6675 independent reflections
Radiation source: fine-focus sealed tube	4532 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
φ and ω scans	θmax = 25.0°, θmin = 3.0°
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor 1997)	h = −18→18
Tmin = 0.969, Tmax = 0.990	k = −18→18
12831 measured reflections	l = −19→19

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.123	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0453P)^2 + 1.8002P] where P = (Fo^2 + 2Fc^2)/3
6675 reflections	(Δ/σ)max < 0.001
418 parameters	Δρmax = 0.45 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

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
P1	0.03298 (4)	0.80431 (4)	0.22404 (4)	0.02553 (15)
N1	0.01341 (11)	0.82305 (11)	0.31760 (11)	0.0264 (4)
N2	0.14675 (11)	0.79731 (11)	0.27670 (11)	0.0266 (4)
Li1	0.1015 (3)	0.7215 (3)	0.3573 (3)	0.0402 (10)
Li2	0.1292 (3)	0.8920 (3)	0.3534 (3)	0.0376 (9)
O1	0.14337 (13)	0.62594 (12)	0.43661 (12)	0.0542 (5)
O2	0.18063 (10)	0.99967 (10)	0.40196 (10)	0.0381 (4)
C1	0.00154 (14)	0.68722 (14)	0.20333 (13)	0.0290 (5)
C2	0.05962 (17)	0.62614 (15)	0.18734 (17)	0.0424 (6)
H2	0.1195	0.6431	0.1922	0.051*
C3	0.03185 (19)	0.54082 (16)	0.16433 (19)	0.0532 (7)
H3	0.0725	0.5003	0.1537	0.064*
C4	−0.05454 (19)	0.51568 (17)	0.15718 (18)	0.0506 (7)
H4	−0.0736	0.4575	0.1420	0.061*
C5	−0.11351 (17)	0.57495 (16)	0.17199 (16)	0.0437 (6)
H5	−0.1733	0.5576	0.1669	0.052*
C6	−0.08586 (15)	0.65972 (15)	0.19422 (14)	0.0338 (5)
H6	−0.1275	0.7000	0.2035	0.041*
C10	−0.07580 (14)	0.85140 (13)	0.30858 (14)	0.0277 (5)
C11	−0.11298 (15)	0.92948 (14)	0.26572 (14)	0.0303 (5)
C12	−0.20357 (16)	0.94950 (15)	0.25223 (15)	0.0377 (6)
H12	−0.2288	1.0007	0.2216	0.045*
C13	−0.25747 (16)	0.89716 (16)	0.28206 (16)	0.0418 (6)
H13	−0.3196	0.9108	0.2702	0.050*
C14	−0.22017 (16)	0.82485 (15)	0.32925 (16)	0.0392 (6)
H14	−0.2563	0.7906	0.3527	0.047*
C15	−0.13090 (15)	0.80061 (14)	0.34352 (14)	0.0306 (5)
C16	−0.05672 (16)	0.99534 (14)	0.23721 (15)	0.0349 (5)
H16	0.0053	0.9701	0.2504	0.042*
C17	−0.09373 (19)	1.01290 (18)	0.14158 (17)	0.0507 (7)
H17A	−0.0967	0.9582	0.1107	0.076*
H17B	−0.0536	1.0537	0.1265	0.076*
H17C	−0.1546	1.0381	0.1263	0.076*
C18	−0.04643 (19)	1.08033 (16)	0.28713 (19)	0.0524 (7)
H18A	−0.1061	1.1071	0.2755	0.079*
H18B	−0.0071	1.1202	0.2698	0.079*
H18C	−0.0194	1.0682	0.3480	0.079*
C19	−0.09255 (16)	0.72198 (14)	0.39858 (16)	0.0372 (6)
H19	−0.0395	0.7009	0.3837	0.045*
C20	−0.1591 (2)	0.64634 (16)	0.3848 (2)	0.0560 (8)
H20A	−0.1277	0.5956	0.4170	0.084*
H20B	−0.1831	0.6319	0.3243	0.084*
H20C	−0.2090	0.6630	0.4044	0.084*
C21	−0.0573 (2)	0.74822 (17)	0.49238 (17)	0.0531 (7)
H21A	−0.1083	0.7666	0.5098	0.080*
H21B	−0.0143	0.7964	0.5005	0.080*
H21C	−0.0269	0.6985	0.5269	0.080*
C22	0.22019 (14)	0.79465 (13)	0.24669 (14)	0.0266 (5)
C23	0.21622 (14)	0.80162 (13)	0.16039 (14)	0.0277 (5)
C24	0.29724 (15)	0.80147 (14)	0.14248 (15)	0.0335 (5)
H24	0.2941	0.8078	0.0851	0.040*
C25	0.38088 (16)	0.79259 (15)	0.20379 (15)	0.0385 (6)
H25	0.4344	0.7923	0.1893	0.046*
C26	0.38510 (15)	0.78414 (15)	0.28694 (15)	0.0380 (6)
H26	0.4426	0.7773	0.3299	0.046*
C27	0.30780 (15)	0.78525 (14)	0.31010 (14)	0.0317 (5)
C28	0.12850 (14)	0.81354 (14)	0.08626 (13)	0.0296 (5)
H28	0.0793	0.7848	0.1022	0.036*
C29	0.10389 (17)	0.90954 (15)	0.07162 (16)	0.0412 (6)
H29A	0.0991	0.9349	0.1237	0.062*
H29B	0.0457	0.9154	0.0255	0.062*
H29C	0.1510	0.9400	0.0563	0.062*
C30	0.12924 (17)	0.77121 (17)	0.00349 (15)	0.0444 (6)
H30A	0.1711	0.8029	−0.0181	0.067*
H30B	0.0681	0.7732	−0.0387	0.067*
H30C	0.1489	0.7106	0.0144	0.067*
C31	0.32141 (16)	0.77539 (17)	0.40392 (15)	0.0396 (6)
H31	0.2605	0.7806	0.4104	0.047*
C32	0.35901 (18)	0.68596 (17)	0.43731 (17)	0.0503 (7)
H32A	0.3154	0.6411	0.4077	0.075*
H32B	0.3694	0.6828	0.4984	0.075*
H32C	0.4164	0.6766	0.4273	0.075*
C33	0.38110 (19)	0.84697 (18)	0.45728 (17)	0.0527 (7)
H33A	0.4413	0.8442	0.4518	0.079*
H33B	0.3867	0.8391	0.5170	0.079*
H33C	0.3537	0.9037	0.4374	0.079*
C34	0.1355 (2)	0.5368 (2)	0.4009 (2)	0.0671 (9)
H34A	0.1439	0.5389	0.3449	0.080*
H34B	0.1838	0.4997	0.4390	0.080*
C35	0.0465 (2)	0.4984 (2)	0.3910 (2)	0.0787 (10)
H35A	0.0393	0.4935	0.4467	0.118*
H35B	0.0425	0.4405	0.3655	0.118*
H35C	−0.0015	0.5356	0.3541	0.118*
C36	0.1703 (2)	0.6252 (2)	0.52730 (19)	0.0634 (8)
H36A	0.2238	0.5870	0.5510	0.076*
H36B	0.1205	0.6015	0.5447	0.076*
C37	0.1928 (2)	0.7146 (2)	0.5615 (2)	0.0735 (9)
H37A	0.2436	0.7371	0.5459	0.110*
H37B	0.2099	0.7134	0.6235	0.110*
H37C	0.1399	0.7524	0.5376	0.110*
C38	0.22324 (19)	1.06189 (16)	0.36288 (18)	0.0501 (7)
H38A	0.2891	1.0646	0.3949	0.060*
H38B	0.1971	1.1204	0.3636	0.060*
C39	0.2078 (2)	1.03446 (19)	0.27322 (18)	0.0585 (8)
H39A	0.2345	0.9769	0.2730	0.088*
H39B	0.2362	1.0765	0.2461	0.088*
H39C	0.1425	1.0320	0.2419	0.088*
C40	0.1824 (2)	1.02817 (17)	0.48366 (17)	0.0531 (7)
H40A	0.1527	1.0857	0.4788	0.064*
H40B	0.2459	1.0341	0.5221	0.064*
C41	0.1340 (2)	0.9638 (2)	0.5192 (2)	0.0736 (10)
H41A	0.0724	0.9553	0.4791	0.110*
H41B	0.1311	0.9853	0.5733	0.110*
H41C	0.1666	0.9083	0.5284	0.110*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.0227 (3)	0.0283 (3)	0.0269 (3)	0.0008 (2)	0.0101 (2)	0.0007 (2)
N1	0.0246 (10)	0.0299 (10)	0.0275 (10)	0.0007 (8)	0.0124 (8)	0.0003 (8)
N2	0.0220 (9)	0.0331 (10)	0.0261 (10)	0.0002 (8)	0.0101 (8)	0.0020 (8)
Li1	0.035 (2)	0.042 (2)	0.046 (3)	0.0001 (18)	0.017 (2)	0.0103 (19)
Li2	0.035 (2)	0.040 (2)	0.039 (2)	−0.0059 (18)	0.0148 (19)	−0.0042 (18)
O1	0.0601 (12)	0.0511 (11)	0.0489 (12)	0.0004 (9)	0.0155 (10)	0.0183 (9)
O2	0.0426 (10)	0.0340 (9)	0.0383 (10)	−0.0065 (7)	0.0147 (8)	−0.0059 (7)
C1	0.0283 (12)	0.0337 (12)	0.0261 (12)	−0.0011 (10)	0.0105 (10)	−0.0006 (10)
C2	0.0375 (14)	0.0343 (13)	0.0623 (18)	0.0014 (11)	0.0260 (14)	−0.0018 (12)
C3	0.0573 (18)	0.0360 (14)	0.076 (2)	0.0034 (13)	0.0353 (17)	−0.0094 (14)
C4	0.0591 (18)	0.0357 (14)	0.0627 (19)	−0.0106 (13)	0.0280 (16)	−0.0057 (13)
C5	0.0426 (15)	0.0456 (15)	0.0458 (16)	−0.0132 (13)	0.0186 (13)	−0.0053 (12)
C6	0.0326 (13)	0.0387 (13)	0.0319 (14)	−0.0025 (10)	0.0130 (11)	−0.0032 (10)
C10	0.0272 (12)	0.0295 (12)	0.0291 (13)	−0.0026 (9)	0.0132 (10)	−0.0062 (10)
C11	0.0305 (13)	0.0315 (12)	0.0304 (13)	0.0020 (10)	0.0123 (11)	−0.0021 (10)
C12	0.0357 (14)	0.0371 (13)	0.0403 (15)	0.0087 (11)	0.0129 (12)	0.0005 (11)
C13	0.0279 (13)	0.0466 (15)	0.0554 (17)	0.0040 (11)	0.0199 (13)	−0.0074 (13)
C14	0.0350 (14)	0.0424 (14)	0.0490 (16)	−0.0035 (11)	0.0260 (13)	−0.0070 (12)
C15	0.0308 (12)	0.0295 (12)	0.0365 (13)	−0.0029 (10)	0.0178 (11)	−0.0060 (10)
C16	0.0375 (13)	0.0301 (12)	0.0396 (14)	0.0055 (11)	0.0164 (12)	0.0069 (10)
C17	0.0546 (17)	0.0528 (16)	0.0472 (17)	0.0085 (14)	0.0203 (14)	0.0150 (13)
C18	0.0605 (18)	0.0364 (14)	0.066 (2)	−0.0060 (13)	0.0288 (16)	−0.0023 (13)
C19	0.0389 (14)	0.0321 (13)	0.0507 (16)	−0.0011 (11)	0.0282 (13)	0.0026 (11)
C20	0.0622 (19)	0.0398 (15)	0.076 (2)	−0.0117 (14)	0.0363 (17)	0.0011 (14)
C21	0.0630 (19)	0.0478 (16)	0.0504 (18)	0.0025 (14)	0.0217 (16)	0.0094 (13)
C22	0.0250 (11)	0.0258 (11)	0.0312 (12)	0.0005 (9)	0.0126 (10)	0.0020 (9)
C23	0.0268 (12)	0.0267 (11)	0.0306 (13)	0.0002 (10)	0.0110 (10)	0.0012 (10)
C24	0.0333 (13)	0.0390 (13)	0.0328 (13)	0.0023 (11)	0.0172 (11)	0.0029 (11)
C25	0.0271 (13)	0.0496 (15)	0.0432 (15)	0.0047 (11)	0.0176 (12)	0.0063 (12)
C26	0.0243 (12)	0.0502 (15)	0.0377 (15)	0.0036 (11)	0.0083 (11)	0.0065 (11)
C27	0.0252 (12)	0.0394 (13)	0.0309 (13)	0.0023 (10)	0.0101 (11)	0.0053 (10)
C28	0.0273 (12)	0.0369 (12)	0.0266 (12)	0.0011 (10)	0.0117 (10)	0.0010 (10)
C29	0.0387 (14)	0.0436 (14)	0.0375 (15)	0.0022 (12)	0.0080 (12)	0.0049 (11)
C30	0.0366 (14)	0.0624 (17)	0.0333 (15)	0.0022 (12)	0.0107 (12)	−0.0061 (12)
C31	0.0253 (13)	0.0609 (16)	0.0313 (14)	0.0034 (11)	0.0081 (11)	0.0081 (12)
C32	0.0448 (16)	0.0618 (17)	0.0421 (16)	−0.0001 (14)	0.0119 (13)	0.0171 (14)
C33	0.0561 (18)	0.0648 (18)	0.0361 (16)	0.0009 (15)	0.0141 (14)	0.0006 (13)
C34	0.077 (2)	0.064 (2)	0.070 (2)	0.0063 (17)	0.0373 (19)	0.0111 (17)
C35	0.091 (3)	0.067 (2)	0.085 (3)	0.006 (2)	0.039 (2)	0.0074 (19)
C36	0.066 (2)	0.069 (2)	0.054 (2)	0.0034 (16)	0.0180 (17)	0.0218 (16)
C37	0.071 (2)	0.089 (3)	0.062 (2)	−0.0142 (19)	0.0238 (18)	0.0080 (18)
C38	0.0511 (17)	0.0394 (15)	0.0574 (18)	−0.0148 (13)	0.0153 (15)	0.0008 (13)
C39	0.0593 (19)	0.0634 (19)	0.0548 (19)	−0.0232 (15)	0.0217 (16)	0.0038 (15)
C40	0.0629 (19)	0.0484 (16)	0.0484 (17)	−0.0011 (14)	0.0193 (15)	−0.0155 (13)
C41	0.085 (2)	0.098 (3)	0.0489 (19)	−0.024 (2)	0.0362 (18)	−0.0169 (17)

Geometric parameters (Å, º)

P1—N2	1.7049 (18)	C21—H21C	0.9800
P1—N1	1.7185 (17)	C22—C23	1.428 (3)
P1—C1	1.868 (2)	C22—C27	1.431 (3)
N1—C10	1.424 (3)	C23—C24	1.400 (3)
N1—Li2	2.011 (4)	C23—C28	1.520 (3)
N1—Li1	2.042 (4)	C24—C25	1.371 (3)
N2—C22	1.404 (2)	C24—H24	0.9500
N2—Li2	2.021 (4)	C25—C26	1.377 (3)
N2—Li1	2.081 (4)	C25—H25	0.9500
Li1—O1	1.939 (4)	C26—C27	1.392 (3)
Li2—O2	1.900 (4)	C26—H26	0.9500
O1—C36	1.431 (3)	C27—C31	1.519 (3)
O1—C34	1.484 (3)	C28—C29	1.525 (3)
O2—C40	1.427 (3)	C28—C30	1.534 (3)
O2—C38	1.444 (3)	C28—H28	1.0000
C1—C6	1.392 (3)	C29—H29A	0.9800
C1—C2	1.396 (3)	C29—H29B	0.9800
C2—C3	1.395 (3)	C29—H29C	0.9800
C2—H2	0.9500	C30—H30A	0.9800
C3—C4	1.374 (4)	C30—H30B	0.9800
C3—H3	0.9500	C30—H30C	0.9800
C4—C5	1.379 (3)	C31—C33	1.523 (4)
C4—H4	0.9500	C31—C32	1.526 (3)
C5—C6	1.385 (3)	C31—H31	1.0000
C5—H5	0.9500	C32—H32A	0.9800
C6—H6	0.9500	C32—H32B	0.9800
C10—C11	1.419 (3)	C32—H32C	0.9800
C10—C15	1.429 (3)	C33—H33A	0.9800
C11—C12	1.395 (3)	C33—H33B	0.9800
C11—C16	1.522 (3)	C33—H33C	0.9800
C12—C13	1.377 (3)	C34—C35	1.471 (4)
C12—H12	0.9500	C34—H34A	0.9900
C13—C14	1.375 (3)	C34—H34B	0.9900
C13—H13	0.9500	C35—H35A	0.9800
C14—C15	1.389 (3)	C35—H35B	0.9800
C14—H14	0.9500	C35—H35C	0.9800
C15—C19	1.516 (3)	C36—C37	1.486 (4)
C16—C18	1.530 (3)	C36—H36A	0.9900
C16—C17	1.530 (3)	C36—H36B	0.9900
C16—H16	1.0000	C37—H37A	0.9800
C17—H17A	0.9800	C37—H37B	0.9800
C17—H17B	0.9800	C37—H37C	0.9800
C17—H17C	0.9800	C38—C39	1.497 (4)
C18—H18A	0.9800	C38—H38A	0.9900
C18—H18B	0.9800	C38—H38B	0.9900
C18—H18C	0.9800	C39—H39A	0.9800
C19—C20	1.527 (3)	C39—H39B	0.9800
C19—C21	1.531 (4)	C39—H39C	0.9800
C19—H19	1.0000	C40—C41	1.488 (4)
C20—H20A	0.9800	C40—H40A	0.9900
C20—H20B	0.9800	C40—H40B	0.9900
C20—H20C	0.9800	C41—H41A	0.9800
C21—H21A	0.9800	C41—H41B	0.9800
C21—H21B	0.9800	C41—H41C	0.9800
N2—P1—N1	91.02 (9)	C23—C22—C27	117.38 (18)
N2—P1—C1	101.50 (9)	C24—C23—C22	118.9 (2)
N1—P1—C1	102.32 (9)	C24—C23—C28	117.49 (19)
C10—N1—P1	115.26 (14)	C22—C23—C28	123.51 (18)
C10—N1—Li2	128.72 (17)	C25—C24—C23	123.2 (2)
P1—N1—Li2	86.47 (13)	C25—C24—H24	118.4
C10—N1—Li1	143.24 (17)	C23—C24—H24	118.4
P1—N1—Li1	81.88 (13)	C24—C25—C26	118.2 (2)
Li2—N1—Li1	82.15 (17)	C24—C25—H25	120.9
C22—N2—P1	131.17 (15)	C26—C25—H25	120.9
C22—N2—Li2	123.56 (17)	C25—C26—C27	122.1 (2)
P1—N2—Li2	86.50 (13)	C25—C26—H26	118.9
C22—N2—Li1	135.75 (17)	C27—C26—H26	118.9
P1—N2—Li1	81.03 (13)	C26—C27—C22	120.2 (2)
Li2—N2—Li1	80.94 (17)	C26—C27—C31	117.1 (2)
O1—Li1—N1	146.9 (2)	C22—C27—C31	122.72 (18)
O1—Li1—N2	139.2 (2)	C23—C28—C29	110.98 (18)
N1—Li1—N2	72.64 (14)	C23—C28—C30	113.86 (18)
O2—Li2—N1	142.9 (2)	C29—C28—C30	110.17 (19)
O2—Li2—N2	140.4 (2)	C23—C28—H28	107.2
N1—Li2—N2	74.57 (15)	C29—C28—H28	107.2
C36—O1—C34	112.0 (2)	C30—C28—H28	107.2
C36—O1—Li1	129.9 (2)	C28—C29—H29A	109.5
C34—O1—Li1	117.5 (2)	C28—C29—H29B	109.5
C40—O2—C38	111.61 (18)	H29A—C29—H29B	109.5
C40—O2—Li2	123.05 (18)	C28—C29—H29C	109.5
C38—O2—Li2	125.34 (18)	H29A—C29—H29C	109.5
C6—C1—C2	117.1 (2)	H29B—C29—H29C	109.5
C6—C1—P1	120.09 (16)	C28—C30—H30A	109.5
C2—C1—P1	122.41 (16)	C28—C30—H30B	109.5
C3—C2—C1	121.5 (2)	H30A—C30—H30B	109.5
C3—C2—H2	119.2	C28—C30—H30C	109.5
C1—C2—H2	119.2	H30A—C30—H30C	109.5
C4—C3—C2	119.7 (2)	H30B—C30—H30C	109.5
C4—C3—H3	120.2	C27—C31—C33	112.2 (2)
C2—C3—H3	120.2	C27—C31—C32	111.7 (2)
C3—C4—C5	120.0 (2)	C33—C31—C32	110.6 (2)
C3—C4—H4	120.0	C27—C31—H31	107.3
C5—C4—H4	120.0	C33—C31—H31	107.3
C4—C5—C6	120.2 (2)	C32—C31—H31	107.3
C4—C5—H5	119.9	C31—C32—H32A	109.5
C6—C5—H5	119.9	C31—C32—H32B	109.5
C5—C6—C1	121.5 (2)	H32A—C32—H32B	109.5
C5—C6—H6	119.2	C31—C32—H32C	109.5
C1—C6—H6	119.2	H32A—C32—H32C	109.5
C11—C10—N1	122.26 (18)	H32B—C32—H32C	109.5
C11—C10—C15	117.89 (19)	C31—C33—H33A	109.5
N1—C10—C15	119.85 (19)	C31—C33—H33B	109.5
C12—C11—C10	119.4 (2)	H33A—C33—H33B	109.5
C12—C11—C16	117.9 (2)	C31—C33—H33C	109.5
C10—C11—C16	122.62 (19)	H33A—C33—H33C	109.5
C13—C12—C11	121.9 (2)	H33B—C33—H33C	109.5
C13—C12—H12	119.1	C35—C34—O1	111.3 (2)
C11—C12—H12	119.1	C35—C34—H34A	109.4
C14—C13—C12	119.1 (2)	O1—C34—H34A	109.4
C14—C13—H13	120.4	C35—C34—H34B	109.4
C12—C13—H13	120.4	O1—C34—H34B	109.4
C13—C14—C15	121.6 (2)	H34A—C34—H34B	108.0
C13—C14—H14	119.2	C34—C35—H35A	109.5
C15—C14—H14	119.2	C34—C35—H35B	109.5
C14—C15—C10	119.8 (2)	H35A—C35—H35B	109.5
C14—C15—C19	119.22 (19)	C34—C35—H35C	109.5
C10—C15—C19	120.97 (19)	H35A—C35—H35C	109.5
C11—C16—C18	111.27 (18)	H35B—C35—H35C	109.5
C11—C16—C17	113.0 (2)	O1—C36—C37	110.3 (2)
C18—C16—C17	110.7 (2)	O1—C36—H36A	109.6
C11—C16—H16	107.2	C37—C36—H36A	109.6
C18—C16—H16	107.2	O1—C36—H36B	109.6
C17—C16—H16	107.2	C37—C36—H36B	109.6
C16—C17—H17A	109.5	H36A—C36—H36B	108.1
C16—C17—H17B	109.5	C36—C37—H37A	109.5
H17A—C17—H17B	109.5	C36—C37—H37B	109.5
C16—C17—H17C	109.5	H37A—C37—H37B	109.5
H17A—C17—H17C	109.5	C36—C37—H37C	109.5
H17B—C17—H17C	109.5	H37A—C37—H37C	109.5
C16—C18—H18A	109.5	H37B—C37—H37C	109.5
C16—C18—H18B	109.5	O2—C38—C39	108.9 (2)
H18A—C18—H18B	109.5	O2—C38—H38A	109.9
C16—C18—H18C	109.5	C39—C38—H38A	109.9
H18A—C18—H18C	109.5	O2—C38—H38B	109.9
H18B—C18—H18C	109.5	C39—C38—H38B	109.9
C15—C19—C20	114.0 (2)	H38A—C38—H38B	108.3
C15—C19—C21	110.12 (19)	C38—C39—H39A	109.5
C20—C19—C21	110.3 (2)	C38—C39—H39B	109.5
C15—C19—H19	107.4	H39A—C39—H39B	109.5
C20—C19—H19	107.4	C38—C39—H39C	109.5
C21—C19—H19	107.4	H39A—C39—H39C	109.5
C19—C20—H20A	109.5	H39B—C39—H39C	109.5
C19—C20—H20B	109.5	O2—C40—C41	109.3 (2)
H20A—C20—H20B	109.5	O2—C40—H40A	109.8
C19—C20—H20C	109.5	C41—C40—H40A	109.8
H20A—C20—H20C	109.5	O2—C40—H40B	109.8
H20B—C20—H20C	109.5	C41—C40—H40B	109.8
C19—C21—H21A	109.5	H40A—C40—H40B	108.3
C19—C21—H21B	109.5	C40—C41—H41A	109.5
H21A—C21—H21B	109.5	C40—C41—H41B	109.5
C19—C21—H21C	109.5	H41A—C41—H41B	109.5
H21A—C21—H21C	109.5	C40—C41—H41C	109.5
H21B—C21—H21C	109.5	H41A—C41—H41C	109.5
N2—C22—C23	126.8 (2)	H41B—C41—H41C	109.5
N2—C22—C27	115.81 (18)