rac-[2-(Dicyclohexylphosphanyl)phenyl](phenyl)phosphinic diisopropyl-amide-borane hemihydrate.

In the title compound, C(30)H(48)BNOP(2)·0.5H(2)O, the water molecule is disordered about an inversion centre. Both phospho-rus atoms shows distortions in their tetra-hedral environments with the cyclo-hexyl substituents disordered over two orientations in a 0.851 (3):0.149 (3) occupancy ratio. The crystal structure is assembled via O-H⋯O inter-actions between pairs of phosphininc amide mol-ecules and water molecules, creating hydrogen-bonded dimers with graph-set R(2) (4)(8) along [001]. Weak C-H⋯O inter-actions are also observed.

Related literature

For background to the synthesis of ligands derived from phosphinic amides, see: Williams et al. (2009 ▶). For background to DoM technology, see: Snieckus (1990 ▶). For details of cone angles, see: Tolman (1977 ▶); Otto (2001 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C30H48BNOP2·0.5H2O

M = 1040.9

Triclinic,

a = 11.2480 (3) Å

b = 11.5240 (3) Å

c = 14.1640 (4) Å

α = 90.543 (2)°

β = 108.178 (1)°

γ = 118.826 (1)°

V = 1499.73 (7) Å3

Z = 1

Mo Kα radiation

μ = 0.17 mm−1

T = 100 K

0.25 × 0.17 × 0.12 mm

Data collection

Bruker X8 APEXII 4K KappaCCD diffractometer

34539 measured reflections

7448 independent reflections

5330 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.134

S = 1.04

7448 reflections

447 parameters

314 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.55 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶) and WinGX (Farrugia, 2012 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813001839/zq2191sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813001839/zq2191Isup2.hkl

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

C30H48BNOP2·0.5H2O	Z = 1
Mr = 1040.9	F(000) = 566
Triclinic, P1	Dx = 1.153 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 11.2480 (3) Å	Cell parameters from 5800 reflections
b = 11.5240 (3) Å	θ = 2.2–25.8°
c = 14.1640 (4) Å	µ = 0.17 mm−1
α = 90.543 (2)°	T = 100 K
β = 108.178 (1)°	Prism, colourless
γ = 118.826 (1)°	0.25 × 0.17 × 0.12 mm
V = 1499.73 (7) Å3

Bruker X8 APEXII 4K KappaCCD diffractometer	5330 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.053
Detector resolution: 8.4 pixels mm-1	θmax = 28.3°, θmin = 2.1°
φ and ω scans	h = −14→15
34539 measured reflections	k = −15→15
7448 independent reflections	l = −18→18

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.058P)2 + 0.5817P] where P = (Fo2 + 2Fc2)/3
7448 reflections	(Δ/σ)max = 0.001
447 parameters	Δρmax = 0.55 e Å−3
314 restraints	Δρmin = −0.27 e Å−3

Experimental. The intensity data was collected on a Bruker X8 APEXII 4 K KappaCCD diffractometer using an exposure time of 20 s/frame. A total of 2529 frames were collected with a frame width of 0.5° covering up to θ = 28.33° with 99.6% completeness accomplished.

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)
P1	0.73833 (5)	0.64726 (5)	0.78185 (4)	0.02098 (13)
P2	0.60597 (5)	0.28217 (5)	0.75649 (4)	0.02207 (13)
O1	0.63962 (15)	0.56005 (13)	0.68112 (10)	0.0288 (3)
N4	0.70251 (17)	0.75742 (16)	0.82270 (12)	0.0257 (4)
C3	0.5686 (2)	0.6994 (2)	0.84861 (16)	0.0308 (5)
H3	0.5525	0.6122	0.8701	0.037*
C4	0.7405 (2)	0.8879 (2)	0.78540 (16)	0.0304 (5)
H4	0.6723	0.9148	0.7952	0.036*
C11	0.7507 (2)	0.55277 (19)	0.88326 (14)	0.0241 (4)
C12	0.71675 (19)	0.41644 (18)	0.87099 (14)	0.0230 (4)
C13	0.7584 (2)	0.3688 (2)	0.95869 (15)	0.0288 (4)
H13	0.739	0.2786	0.9519	0.035*
C14	0.8263 (2)	0.4469 (2)	1.05460 (16)	0.0351 (5)
H14	0.8554	0.4114	1.1119	0.042*
C15	0.8515 (2)	0.5762 (2)	1.06664 (16)	0.0345 (5)
H15	0.8937	0.6294	1.1324	0.041*
C16	0.8147 (2)	0.6280 (2)	0.98160 (15)	0.0298 (4)
H16	0.8335	0.7179	0.9904	0.036*
C21	0.9236 (2)	0.7385 (2)	0.78428 (16)	0.0291 (4)
C22	1.0458 (2)	0.8007 (2)	0.87218 (18)	0.0355 (5)
H22	1.0346	0.8015	0.9359	0.043*
C23	1.1844 (2)	0.8617 (2)	0.8683 (2)	0.0426 (6)
H23	1.2675	0.9058	0.929	0.051*
C24	1.2010 (3)	0.8581 (2)	0.7754 (2)	0.0495 (7)
H24	1.2954	0.8977	0.7722	0.059*
C25	1.0792 (3)	0.7966 (2)	0.6878 (2)	0.0463 (6)
H25	1.0907	0.7961	0.6241	0.056*
C26	0.9422 (3)	0.7363 (2)	0.69121 (19)	0.0385 (5)
H26	0.8596	0.6928	0.6303	0.046*
C31	0.4312 (2)	0.6669 (2)	0.75826 (17)	0.0359 (5)
H31A	0.4402	0.7509	0.7379	0.054*
H31B	0.3458	0.6204	0.7779	0.054*
H31C	0.4201	0.6086	0.7014	0.054*
C32	0.5886 (3)	0.7900 (2)	0.93776 (17)	0.0403 (5)
H32A	0.6768	0.8101	0.9944	0.06*
H32B	0.5041	0.744	0.9585	0.06*
H32C	0.5977	0.8743	0.9179	0.06*
C41	0.7158 (3)	0.8768 (2)	0.67253 (17)	0.0390 (5)
H41A	0.7899	0.8638	0.6601	0.059*
H41B	0.7227	0.9598	0.6512	0.059*
H41C	0.619	0.7998	0.6339	0.059*
C42	0.8933 (2)	1.0017 (2)	0.84945 (19)	0.0377 (5)
H42A	0.9068	1.0037	0.9214	0.057*
H42B	0.9058	1.0881	0.8323	0.057*
H42C	0.9653	0.9865	0.8358	0.057*
C51A	0.4322 (2)	0.2804 (3)	0.7140 (2)	0.0250 (6)	0.851 (3)
H51A	0.4547	0.3739	0.7053	0.03*	0.851 (3)
C52A	0.3642 (3)	0.2451 (3)	0.7958 (2)	0.0300 (6)	0.851 (3)
H52A	0.3482	0.1558	0.8102	0.036*	0.851 (3)
H52B	0.4322	0.3129	0.859	0.036*	0.851 (3)
C53A	0.2193 (3)	0.2417 (3)	0.7622 (3)	0.0391 (6)	0.851 (3)
H53A	0.1755	0.2139	0.8147	0.047*	0.851 (3)
H53B	0.2367	0.3332	0.7545	0.047*	0.851 (3)
C54A	0.1149 (3)	0.1443 (3)	0.6627 (3)	0.0452 (8)	0.851 (3)
H54A	0.0227	0.145	0.6418	0.054*	0.851 (3)
H54B	0.0928	0.0517	0.6712	0.054*	0.851 (3)
C55A	0.1812 (3)	0.1839 (3)	0.5812 (2)	0.0443 (7)	0.851 (3)
H55A	0.1982	0.2745	0.5701	0.053*	0.851 (3)
H55B	0.1122	0.1189	0.5168	0.053*	0.851 (3)
C56A	0.3250 (3)	0.1857 (3)	0.6117 (2)	0.0343 (6)	0.851 (3)
H56A	0.3683	0.216	0.5592	0.041*	0.851 (3)
H56B	0.3066	0.0932	0.6164	0.041*	0.851 (3)
C51B	0.4299 (11)	0.2635 (18)	0.6799 (11)	0.033 (2)	0.149 (3)
H51B	0.4438	0.3364	0.6393	0.039*	0.149 (3)
C52B	0.3637 (15)	0.2733 (17)	0.7555 (13)	0.0363 (19)	0.149 (3)
H52C	0.4275	0.3627	0.8011	0.044*	0.149 (3)
H52D	0.3552	0.2032	0.7972	0.044*	0.149 (3)
C53B	0.2107 (14)	0.2536 (16)	0.6988 (14)	0.042 (2)	0.149 (3)
H53C	0.1644	0.2496	0.7487	0.05*	0.149 (3)
H53D	0.2227	0.3333	0.6677	0.05*	0.149 (3)
C54B	0.1124 (17)	0.131 (2)	0.6188 (14)	0.041 (2)	0.149 (3)
H54C	0.027	0.1357	0.5767	0.049*	0.149 (3)
H54D	0.077	0.0509	0.651	0.049*	0.149 (3)
C55B	0.1864 (14)	0.1125 (18)	0.5510 (11)	0.042 (2)	0.149 (3)
H55C	0.1206	0.0229	0.5057	0.051*	0.149 (3)
H55D	0.2032	0.1819	0.5081	0.051*	0.149 (3)
C56B	0.3309 (14)	0.1234 (16)	0.6109 (12)	0.035 (2)	0.149 (3)
H56C	0.3762	0.1125	0.5643	0.042*	0.149 (3)
H56D	0.3156	0.0521	0.6521	0.042*	0.149 (3)
C61A	0.6890 (3)	0.3241 (4)	0.65939 (19)	0.0264 (6)	0.851 (3)
H61A	0.664	0.3876	0.6226	0.032*	0.851 (3)
C62A	0.6305 (3)	0.1964 (3)	0.5823 (2)	0.0338 (6)	0.851 (3)
H62A	0.6542	0.1321	0.6174	0.041*	0.851 (3)
H62B	0.5234	0.1517	0.5498	0.041*	0.851 (3)
C63A	0.6999 (3)	0.2363 (3)	0.5022 (2)	0.0452 (7)	0.851 (3)
H63A	0.663	0.1545	0.4528	0.054*	0.851 (3)
H63B	0.6719	0.297	0.4653	0.054*	0.851 (3)
C64A	0.8652 (4)	0.3072 (4)	0.5497 (3)	0.0506 (8)	0.851 (3)
H64A	0.8939	0.2437	0.5809	0.061*	0.851 (3)
H64B	0.9075	0.3363	0.4966	0.061*	0.851 (3)
C65A	0.9237 (4)	0.4289 (3)	0.6295 (3)	0.0503 (8)	0.851 (3)
H65A	0.9062	0.4973	0.5963	0.06*	0.851 (3)
H65B	1.0301	0.4692	0.6632	0.06*	0.851 (3)
C66A	0.8532 (3)	0.3931 (3)	0.7089 (2)	0.0357 (7)	0.851 (3)
H66A	0.8793	0.3325	0.7476	0.043*	0.851 (3)
H66B	0.8902	0.4763	0.757	0.043*	0.851 (3)
C61B	0.7166 (16)	0.335 (3)	0.6756 (11)	0.030 (2)	0.149 (3)
H61B	0.7345	0.4276	0.6682	0.037*	0.149 (3)
C62B	0.6575 (16)	0.2600 (18)	0.5653 (11)	0.0366 (19)	0.149 (3)
H62C	0.632	0.1651	0.5667	0.044*	0.149 (3)
H62D	0.5666	0.2591	0.5275	0.044*	0.149 (3)
C63B	0.7597 (17)	0.318 (2)	0.5077 (11)	0.044 (2)	0.149 (3)
H63C	0.7678	0.4049	0.4923	0.053*	0.149 (3)
H63D	0.717	0.2559	0.4424	0.053*	0.149 (3)
C64B	0.9113 (18)	0.343 (2)	0.5639 (14)	0.045 (2)	0.149 (3)
H64C	0.9067	0.2551	0.5667	0.054*	0.149 (3)
H64D	0.9754	0.3933	0.5264	0.054*	0.149 (3)
C65B	0.9745 (17)	0.4207 (18)	0.6688 (13)	0.041 (2)	0.149 (3)
H65C	0.9963	0.5145	0.6662	0.049*	0.149 (3)
H65D	1.0669	0.424	0.7061	0.049*	0.149 (3)
C66B	0.8695 (18)	0.3561 (19)	0.7245 (13)	0.033 (2)	0.149 (3)
H66C	0.9147	0.4127	0.7928	0.039*	0.149 (3)
H66D	0.8592	0.2671	0.7338	0.039*	0.149 (3)
B1	0.5842 (3)	0.1134 (2)	0.79117 (19)	0.0307 (5)
H1A	0.5426	0.0925	0.8444	0.046*
H1B	0.6796	0.1205	0.8156	0.046*
H1C	0.5193	0.0412	0.7312	0.046*
O2	0.6069 (4)	0.5108 (4)	0.4803 (3)	0.0472 (9)	0.5
H7A	0.607 (5)	0.535 (5)	0.537 (4)	0.036 (14)*	0.5
H7B	0.520 (7)	0.477 (6)	0.432 (5)	0.068 (19)*	0.5

	U11	U22	U33	U12	U13	U23
P1	0.0277 (2)	0.0175 (2)	0.0217 (3)	0.01398 (19)	0.00962 (19)	0.00457 (18)
P2	0.0256 (2)	0.0174 (2)	0.0231 (3)	0.01272 (19)	0.00571 (19)	0.00282 (18)
O1	0.0438 (8)	0.0212 (7)	0.0208 (7)	0.0187 (6)	0.0076 (6)	0.0038 (5)
N4	0.0326 (8)	0.0230 (8)	0.0288 (9)	0.0182 (7)	0.0130 (7)	0.0063 (7)
C3	0.0360 (10)	0.0287 (11)	0.0372 (12)	0.0202 (9)	0.0184 (9)	0.0117 (9)
C4	0.0336 (10)	0.0234 (10)	0.0405 (12)	0.0183 (8)	0.0148 (9)	0.0090 (9)
C11	0.0305 (9)	0.0214 (9)	0.0215 (10)	0.0151 (8)	0.0077 (7)	0.0041 (7)
C12	0.0275 (9)	0.0210 (9)	0.0229 (10)	0.0143 (7)	0.0086 (7)	0.0037 (7)
C13	0.0414 (11)	0.0223 (10)	0.0265 (11)	0.0199 (9)	0.0105 (9)	0.0064 (8)
C14	0.0529 (13)	0.0313 (11)	0.0234 (11)	0.0263 (10)	0.0083 (9)	0.0083 (9)
C15	0.0473 (12)	0.0341 (12)	0.0222 (11)	0.0242 (10)	0.0070 (9)	0.0029 (9)
C16	0.0396 (11)	0.0228 (10)	0.0270 (11)	0.0177 (9)	0.0090 (9)	0.0035 (8)
C21	0.0393 (11)	0.0240 (10)	0.0347 (11)	0.0209 (9)	0.0184 (9)	0.0110 (8)
C22	0.0380 (11)	0.0279 (11)	0.0481 (14)	0.0210 (9)	0.0176 (10)	0.0107 (10)
C23	0.0365 (11)	0.0267 (11)	0.0637 (17)	0.0161 (9)	0.0168 (11)	0.0135 (11)
C24	0.0471 (14)	0.0302 (12)	0.088 (2)	0.0218 (11)	0.0412 (14)	0.0166 (13)
C25	0.0608 (15)	0.0315 (12)	0.0611 (17)	0.0233 (11)	0.0400 (14)	0.0107 (12)
C26	0.0511 (13)	0.0276 (11)	0.0461 (14)	0.0215 (10)	0.0267 (11)	0.0099 (10)
C31	0.0355 (11)	0.0321 (11)	0.0387 (13)	0.0170 (9)	0.0120 (9)	0.0087 (9)
C32	0.0497 (13)	0.0486 (14)	0.0362 (13)	0.0320 (11)	0.0203 (10)	0.0098 (11)
C41	0.0516 (13)	0.0363 (12)	0.0416 (13)	0.0298 (11)	0.0193 (11)	0.0201 (10)
C42	0.0372 (11)	0.0193 (10)	0.0559 (15)	0.0154 (9)	0.0141 (10)	0.0043 (10)
C51A	0.0274 (10)	0.0239 (11)	0.0286 (13)	0.0158 (8)	0.0113 (9)	0.0094 (11)
C52A	0.0350 (11)	0.0291 (12)	0.0366 (14)	0.0199 (9)	0.0201 (10)	0.0118 (10)
C53A	0.0389 (12)	0.0375 (13)	0.0571 (17)	0.0247 (10)	0.0282 (12)	0.0198 (12)
C54A	0.0298 (11)	0.0462 (15)	0.0613 (18)	0.0201 (10)	0.0173 (13)	0.0224 (15)
C55A	0.0287 (11)	0.0478 (15)	0.0492 (16)	0.0189 (11)	0.0061 (11)	0.0128 (13)
C56A	0.0274 (10)	0.0370 (14)	0.0338 (12)	0.0153 (10)	0.0073 (9)	0.0064 (11)
C51B	0.029 (3)	0.031 (3)	0.035 (3)	0.015 (2)	0.009 (3)	0.010 (3)
C52B	0.035 (2)	0.032 (2)	0.044 (3)	0.018 (2)	0.015 (2)	0.010 (2)
C53B	0.032 (2)	0.042 (3)	0.057 (3)	0.025 (2)	0.016 (3)	0.012 (3)
C54B	0.029 (3)	0.044 (3)	0.052 (3)	0.021 (2)	0.013 (3)	0.012 (3)
C55B	0.030 (3)	0.043 (3)	0.045 (3)	0.015 (3)	0.008 (3)	0.010 (3)
C56B	0.027 (3)	0.035 (3)	0.038 (3)	0.015 (3)	0.007 (3)	0.008 (3)
C61A	0.0375 (13)	0.0288 (12)	0.0232 (12)	0.0243 (12)	0.0111 (10)	0.0051 (11)
C62A	0.0447 (13)	0.0281 (13)	0.0335 (13)	0.0209 (11)	0.0162 (10)	0.0003 (11)
C63A	0.0618 (16)	0.0385 (15)	0.0406 (14)	0.0247 (13)	0.0268 (12)	−0.0010 (12)
C64A	0.0579 (18)	0.0484 (18)	0.0600 (17)	0.0282 (14)	0.0376 (15)	0.0018 (14)
C65A	0.0438 (15)	0.0472 (15)	0.0622 (19)	0.0167 (12)	0.0332 (13)	−0.0007 (14)
C66A	0.0325 (12)	0.0349 (15)	0.0424 (15)	0.0172 (10)	0.0170 (11)	0.0013 (12)
C61B	0.040 (3)	0.030 (3)	0.032 (3)	0.025 (3)	0.014 (3)	0.004 (3)
C62B	0.046 (2)	0.034 (2)	0.035 (2)	0.024 (2)	0.016 (2)	0.004 (2)
C63B	0.052 (3)	0.042 (3)	0.044 (3)	0.022 (3)	0.027 (3)	0.003 (3)
C64B	0.046 (3)	0.042 (3)	0.053 (3)	0.021 (3)	0.027 (3)	0.005 (3)
C65B	0.039 (3)	0.038 (3)	0.046 (3)	0.017 (3)	0.022 (3)	0.005 (3)
C66B	0.035 (3)	0.031 (3)	0.037 (3)	0.019 (3)	0.016 (3)	0.005 (3)
B1	0.0381 (12)	0.0195 (11)	0.0349 (13)	0.0176 (9)	0.0089 (10)	0.0056 (9)
O2	0.053 (2)	0.063 (2)	0.0239 (18)	0.0325 (19)	0.0070 (16)	0.0043 (16)

P1—O1	1.4788 (14)	C54A—H54B	0.99
P1—N4	1.6534 (16)	C55A—C56A	1.529 (4)
P1—C21	1.814 (2)	C55A—H55A	0.99
P1—C11	1.822 (2)	C55A—H55B	0.99
P2—C61A	1.837 (2)	C56A—H56A	0.99
P2—C51B	1.841 (5)	C56A—H56B	0.99
P2—C61B	1.845 (5)	C51B—C52B	1.512 (16)
P2—C51A	1.846 (2)	C51B—C56B	1.536 (16)
P2—C12	1.8465 (19)	C51B—H51B	1
P2—B1	1.929 (2)	C52B—C53B	1.554 (15)
N4—C3	1.493 (3)	C52B—H52C	0.99
N4—C4	1.503 (3)	C52B—H52D	0.99
C3—C32	1.519 (3)	C53B—C54B	1.479 (16)
C3—C31	1.538 (3)	C53B—H53C	0.99
C3—H3	1	C53B—H53D	0.99
C4—C42	1.526 (3)	C54B—C55B	1.524 (16)
C4—C41	1.528 (3)	C54B—H54C	0.99
C4—H4	1	C54B—H54D	0.99
C11—C16	1.400 (3)	C55B—C56B	1.523 (15)
C11—C12	1.421 (3)	C55B—H55C	0.99
C12—C13	1.401 (3)	C55B—H55D	0.99
C13—C14	1.380 (3)	C56B—H56C	0.99
C13—H13	0.95	C56B—H56D	0.99
C14—C15	1.374 (3)	C61A—C66A	1.516 (4)
C14—H14	0.95	C61A—C62A	1.542 (4)
C15—C16	1.386 (3)	C61A—H61A	1
C15—H15	0.95	C62A—C63A	1.525 (4)
C16—H16	0.95	C62A—H62A	0.99
C21—C22	1.385 (3)	C62A—H62B	0.99
C21—C26	1.400 (3)	C63A—C64A	1.523 (4)
C22—C23	1.386 (3)	C63A—H63A	0.99
C22—H22	0.95	C63A—H63B	0.99
C23—C24	1.389 (4)	C64A—C65A	1.514 (4)
C23—H23	0.95	C64A—H64A	0.99
C24—C25	1.380 (4)	C64A—H64B	0.99
C24—H24	0.95	C65A—C66A	1.522 (4)
C25—C26	1.369 (3)	C65A—H65A	0.99
C25—H25	0.95	C65A—H65B	0.99
C26—H26	0.95	C66A—H66A	0.99
C31—H31A	0.98	C66A—H66B	0.99
C31—H31B	0.98	C61B—C66B	1.532 (17)
C31—H31C	0.98	C61B—C62B	1.550 (15)
C32—H32A	0.98	C61B—H61B	1
C32—H32B	0.98	C62B—C63B	1.514 (15)
C32—H32C	0.98	C62B—H62C	0.99
C41—H41A	0.98	C62B—H62D	0.99
C41—H41B	0.98	C63B—C64B	1.518 (16)
C41—H41C	0.98	C63B—H63C	0.99
C42—H42A	0.98	C63B—H63D	0.99
C42—H42B	0.98	C64B—C65B	1.489 (16)
C42—H42C	0.98	C64B—H64C	0.99
C51A—C56A	1.534 (3)	C64B—H64D	0.99
C51A—C52A	1.534 (4)	C65B—C66B	1.522 (15)
C51A—H51A	1	C65B—H65C	0.99
C52A—C53A	1.529 (3)	C65B—H65D	0.99
C52A—H52A	0.99	C66B—H66C	0.99
C52A—H52B	0.99	C66B—H66D	0.99
C53A—C54A	1.513 (4)	B1—H1A	0.98
C53A—H53A	0.99	B1—H1B	0.98
C53A—H53B	0.99	B1—H1C	0.98
C54A—C55A	1.521 (4)	O2—H7A	0.85 (5)
C54A—H54A	0.99	O2—H7B	0.88 (7)
O1—P1—N4	117.42 (8)	H55A—C55A—H55B	108
O1—P1—C21	109.44 (9)	C55A—C56A—C51A	110.9 (2)
N4—P1—C21	108.16 (9)	C55A—C56A—H56A	109.5
O1—P1—C11	113.32 (8)	C51A—C56A—H56A	109.5
N4—P1—C11	104.61 (9)	C55A—C56A—H56B	109.5
C21—P1—C11	102.77 (9)	C51A—C56A—H56B	109.5
C61A—P2—C51B	97.4 (6)	H56A—C56A—H56B	108
C51B—P2—C61B	105.8 (9)	C52B—C51B—C56B	109.0 (13)
C61A—P2—C51A	110.78 (14)	C52B—C51B—P2	105.3 (9)
C61B—P2—C51A	118.6 (7)	C56B—C51B—P2	109.7 (9)
C61A—P2—C12	111.28 (12)	C52B—C51B—H51B	110.9
C51B—P2—C12	116.4 (5)	C56B—C51B—H51B	110.9
C61B—P2—C12	104.2 (7)	P2—C51B—H51B	110.9
C51A—P2—C12	102.55 (11)	C51B—C52B—C53B	109.9 (11)
C61A—P2—B1	109.57 (17)	C51B—C52B—H52C	109.7
C51B—P2—B1	111.7 (6)	C53B—C52B—H52C	109.7
C61B—P2—B1	108.3 (10)	C51B—C52B—H52D	109.7
C51A—P2—B1	112.63 (12)	C53B—C52B—H52D	109.7
C12—P2—B1	109.89 (10)	H52C—C52B—H52D	108.2
C3—N4—C4	114.18 (15)	C54B—C53B—C52B	114.1 (12)
C3—N4—P1	115.94 (13)	C54B—C53B—H53C	108.7
C4—N4—P1	121.98 (13)	C52B—C53B—H53C	108.7
N4—C3—C32	111.47 (17)	C54B—C53B—H53D	108.7
N4—C3—C31	113.27 (17)	C52B—C53B—H53D	108.7
C32—C3—C31	110.55 (18)	H53C—C53B—H53D	107.6
N4—C3—H3	107.1	C53B—C54B—C55B	112.7 (14)
C32—C3—H3	107.1	C53B—C54B—H54C	109.1
C31—C3—H3	107.1	C55B—C54B—H54C	109.1
N4—C4—C42	112.22 (17)	C53B—C54B—H54D	109.1
N4—C4—C41	114.47 (17)	C55B—C54B—H54D	109.1
C42—C4—C41	111.57 (19)	H54C—C54B—H54D	107.8
N4—C4—H4	105.9	C56B—C55B—C54B	112.7 (13)
C42—C4—H4	105.9	C56B—C55B—H55C	109.1
C41—C4—H4	105.9	C54B—C55B—H55C	109.1
C16—C11—C12	118.45 (18)	C56B—C55B—H55D	109.1
C16—C11—P1	115.44 (14)	C54B—C55B—H55D	109.1
C12—C11—P1	125.71 (14)	H55C—C55B—H55D	107.8
C13—C12—C11	117.30 (17)	C55B—C56B—C51B	107.5 (11)
C13—C12—P2	112.72 (14)	C55B—C56B—H56C	110.2
C11—C12—P2	129.60 (14)	C51B—C56B—H56C	110.2
C14—C13—C12	122.96 (19)	C55B—C56B—H56D	110.2
C14—C13—H13	118.5	C51B—C56B—H56D	110.2
C12—C13—H13	118.5	H56C—C56B—H56D	108.5
C15—C14—C13	119.58 (19)	C66A—C61A—C62A	110.0 (3)
C15—C14—H14	120.2	C66A—C61A—P2	109.94 (19)
C13—C14—H14	120.2	C62A—C61A—P2	111.0 (2)
C14—C15—C16	119.17 (19)	C66A—C61A—H61A	108.6
C14—C15—H15	120.4	C62A—C61A—H61A	108.6
C16—C15—H15	120.4	P2—C61A—H61A	108.6
C15—C16—C11	122.38 (19)	C63A—C62A—C61A	109.1 (2)
C15—C16—H16	118.8	C63A—C62A—H62A	109.9
C11—C16—H16	118.8	C61A—C62A—H62A	109.9
C22—C21—C26	118.8 (2)	C63A—C62A—H62B	109.9
C22—C21—P1	124.06 (17)	C61A—C62A—H62B	109.9
C26—C21—P1	116.97 (16)	H62A—C62A—H62B	108.3
C21—C22—C23	120.8 (2)	C64A—C63A—C62A	111.3 (3)
C21—C22—H22	119.6	C64A—C63A—H63A	109.4
C23—C22—H22	119.6	C62A—C63A—H63A	109.4
C22—C23—C24	119.7 (2)	C64A—C63A—H63B	109.4
C22—C23—H23	120.2	C62A—C63A—H63B	109.4
C24—C23—H23	120.2	H63A—C63A—H63B	108
C25—C24—C23	119.5 (2)	C65A—C64A—C63A	110.3 (3)
C25—C24—H24	120.2	C65A—C64A—H64A	109.6
C23—C24—H24	120.2	C63A—C64A—H64A	109.6
C26—C25—C24	121.0 (2)	C65A—C64A—H64B	109.6
C26—C25—H25	119.5	C63A—C64A—H64B	109.6
C24—C25—H25	119.5	H64A—C64A—H64B	108.1
C25—C26—C21	120.2 (2)	C64A—C65A—C66A	112.4 (3)
C25—C26—H26	119.9	C64A—C65A—H65A	109.1
C21—C26—H26	119.9	C66A—C65A—H65A	109.1
C3—C31—H31A	109.5	C64A—C65A—H65B	109.1
C3—C31—H31B	109.5	C66A—C65A—H65B	109.1
H31A—C31—H31B	109.5	H65A—C65A—H65B	107.9
C3—C31—H31C	109.5	C61A—C66A—C65A	110.6 (3)
H31A—C31—H31C	109.5	C61A—C66A—H66A	109.5
H31B—C31—H31C	109.5	C65A—C66A—H66A	109.5
C3—C32—H32A	109.5	C61A—C66A—H66B	109.5
C3—C32—H32B	109.5	C65A—C66A—H66B	109.5
H32A—C32—H32B	109.5	H66A—C66A—H66B	108.1
C3—C32—H32C	109.5	C66B—C61B—C62B	105.9 (14)
H32A—C32—H32C	109.5	C66B—C61B—P2	114.9 (12)
H32B—C32—H32C	109.5	C62B—C61B—P2	122.1 (11)
C4—C41—H41A	109.5	C66B—C61B—H61B	104
C4—C41—H41B	109.5	C62B—C61B—H61B	104
H41A—C41—H41B	109.5	P2—C61B—H61B	104
C4—C41—H41C	109.5	C63B—C62B—C61B	115.7 (11)
H41A—C41—H41C	109.5	C63B—C62B—H62C	108.3
H41B—C41—H41C	109.5	C61B—C62B—H62C	108.3
C4—C42—H42A	109.5	C63B—C62B—H62D	108.3
C4—C42—H42B	109.5	C61B—C62B—H62D	108.3
H42A—C42—H42B	109.5	H62C—C62B—H62D	107.4
C4—C42—H42C	109.5	C62B—C63B—C64B	114.0 (14)
H42A—C42—H42C	109.5	C62B—C63B—H63C	108.7
H42B—C42—H42C	109.5	C64B—C63B—H63C	108.7
C56A—C51A—C52A	111.3 (2)	C62B—C63B—H63D	108.7
C56A—C51A—P2	112.73 (18)	C64B—C63B—H63D	108.7
C52A—C51A—P2	110.16 (17)	H63C—C63B—H63D	107.6
C56A—C51A—H51A	107.5	C65B—C64B—C63B	111.8 (14)
C52A—C51A—H51A	107.5	C65B—C64B—H64C	109.3
P2—C51A—H51A	107.5	C63B—C64B—H64C	109.3
C53A—C52A—C51A	111.3 (2)	C65B—C64B—H64D	109.3
C53A—C52A—H52A	109.4	C63B—C64B—H64D	109.3
C51A—C52A—H52A	109.4	H64C—C64B—H64D	107.9
C53A—C52A—H52B	109.4	C64B—C65B—C66B	110.9 (14)
C51A—C52A—H52B	109.4	C64B—C65B—H65C	109.5
H52A—C52A—H52B	108	C66B—C65B—H65C	109.5
C54A—C53A—C52A	111.0 (2)	C64B—C65B—H65D	109.5
C54A—C53A—H53A	109.4	C66B—C65B—H65D	109.5
C52A—C53A—H53A	109.4	H65C—C65B—H65D	108.1
C54A—C53A—H53B	109.4	C65B—C66B—C61B	117.4 (12)
C52A—C53A—H53B	109.4	C65B—C66B—H66C	107.9
H53A—C53A—H53B	108	C61B—C66B—H66C	107.9
C53A—C54A—C55A	110.3 (2)	C65B—C66B—H66D	107.9
C53A—C54A—H54A	109.6	C61B—C66B—H66D	107.9
C55A—C54A—H54A	109.6	H66C—C66B—H66D	107.2
C53A—C54A—H54B	109.6	P2—B1—H1A	109.5
C55A—C54A—H54B	109.6	P2—B1—H1B	109.5
H54A—C54A—H54B	108.1	H1A—B1—H1B	109.5
C54A—C55A—C56A	110.9 (2)	P2—B1—H1C	109.5
C54A—C55A—H55A	109.5	H1A—B1—H1C	109.5
C56A—C55A—H55A	109.5	H1B—B1—H1C	109.5
C54A—C55A—H55B	109.5	H7A—O2—H7B	112 (5)
C56A—C55A—H55B	109.5
O1—P1—N4—C3	69.09 (16)	B1—P2—C51A—C52A	56.8 (2)
C21—P1—N4—C3	−166.52 (14)	C56A—C51A—C52A—C53A	−53.8 (3)
C11—P1—N4—C3	−57.50 (15)	P2—C51A—C52A—C53A	−179.52 (18)
O1—P1—N4—C4	−78.11 (16)	C51A—C52A—C53A—C54A	56.1 (3)
C21—P1—N4—C4	46.27 (17)	C52A—C53A—C54A—C55A	−58.2 (3)
C11—P1—N4—C4	155.29 (14)	C53A—C54A—C55A—C56A	58.5 (4)
C4—N4—C3—C32	−65.0 (2)	C54A—C55A—C56A—C51A	−56.4 (3)
P1—N4—C3—C32	145.22 (15)	C52A—C51A—C56A—C55A	53.9 (3)
C4—N4—C3—C31	60.4 (2)	P2—C51A—C56A—C55A	178.20 (19)
P1—N4—C3—C31	−89.35 (19)	C61A—P2—C51B—C52B	−162.1 (11)
C3—N4—C4—C42	122.81 (19)	C61B—P2—C51B—C52B	−159.1 (14)
P1—N4—C4—C42	−89.5 (2)	C51A—P2—C51B—C52B	−13.3 (17)
C3—N4—C4—C41	−108.7 (2)	C12—P2—C51B—C52B	−43.9 (13)
P1—N4—C4—C41	39.0 (2)	B1—P2—C51B—C52B	83.4 (12)
O1—P1—C11—C16	−165.89 (15)	C61A—P2—C51B—C56B	80.7 (12)
N4—P1—C11—C16	−36.79 (17)	C61B—P2—C51B—C56B	83.8 (15)
C21—P1—C11—C16	76.12 (17)	C51A—P2—C51B—C56B	−130 (3)
O1—P1—C11—C12	21.5 (2)	C12—P2—C51B—C56B	−161.1 (10)
N4—P1—C11—C12	150.64 (16)	B1—P2—C51B—C56B	−33.8 (13)
C21—P1—C11—C12	−96.45 (18)	C56B—C51B—C52B—C53B	−60.3 (16)
C16—C11—C12—C13	−4.0 (3)	P2—C51B—C52B—C53B	−178.0 (11)
P1—C11—C12—C13	168.39 (15)	C51B—C52B—C53B—C54B	52 (2)
C16—C11—C12—P2	168.39 (16)	C52B—C53B—C54B—C55B	−46 (2)
P1—C11—C12—P2	−19.2 (3)	C53B—C54B—C55B—C56B	51 (2)
C61A—P2—C12—C13	−123.2 (2)	C54B—C55B—C56B—C51B	−58.9 (19)
C51B—P2—C12—C13	126.5 (7)	C52B—C51B—C56B—C55B	64.2 (15)
C61B—P2—C12—C13	−117.5 (9)	P2—C51B—C56B—C55B	179.0 (11)
C51A—P2—C12—C13	118.32 (17)	C51B—P2—C61A—C66A	160.1 (6)
B1—P2—C12—C13	−1.66 (18)	C61B—P2—C61A—C66A	−1 (7)
C61A—P2—C12—C11	64.1 (2)	C51A—P2—C61A—C66A	151.5 (3)
C51B—P2—C12—C11	−46.2 (7)	C12—P2—C61A—C66A	38.0 (3)
C61B—P2—C12—C11	69.9 (9)	B1—P2—C61A—C66A	−83.7 (3)
C51A—P2—C12—C11	−54.3 (2)	C51B—P2—C61A—C62A	−78.0 (6)
B1—P2—C12—C11	−174.31 (18)	C61B—P2—C61A—C62A	121 (7)
C11—C12—C13—C14	1.7 (3)	C51A—P2—C61A—C62A	−86.7 (3)
P2—C12—C13—C14	−171.94 (17)	C12—P2—C61A—C62A	159.9 (2)
C12—C13—C14—C15	2.0 (3)	B1—P2—C61A—C62A	38.2 (3)
C13—C14—C15—C16	−3.2 (3)	C66A—C61A—C62A—C63A	−59.3 (3)
C14—C15—C16—C11	0.8 (3)	P2—C61A—C62A—C63A	178.9 (2)
C12—C11—C16—C15	2.9 (3)	C61A—C62A—C63A—C64A	58.8 (3)
P1—C11—C16—C15	−170.28 (17)	C62A—C63A—C64A—C65A	−56.2 (4)
O1—P1—C21—C22	−162.56 (17)	C63A—C64A—C65A—C66A	54.3 (4)
N4—P1—C21—C22	68.41 (19)	C62A—C61A—C66A—C65A	57.7 (4)
C11—P1—C21—C22	−41.9 (2)	P2—C61A—C66A—C65A	−179.9 (2)
O1—P1—C21—C26	12.57 (19)	C64A—C65A—C66A—C61A	−55.8 (4)
N4—P1—C21—C26	−116.46 (17)	C61A—P2—C61B—C66B	−160 (8)
C11—P1—C21—C26	133.27 (17)	C51B—P2—C61B—C66B	−179.7 (17)
C26—C21—C22—C23	1.1 (3)	C51A—P2—C61B—C66B	170.2 (14)
P1—C21—C22—C23	176.13 (17)	C12—P2—C61B—C66B	57 (2)
C21—C22—C23—C24	−1.4 (3)	B1—P2—C61B—C66B	−59.9 (18)
C22—C23—C24—C25	1.6 (4)	C61A—P2—C61B—C62B	−30 (5)
C23—C24—C25—C26	−1.5 (4)	C51B—P2—C61B—C62B	−49 (2)
C24—C25—C26—C21	1.3 (4)	C51A—P2—C61B—C62B	−59 (2)
C22—C21—C26—C25	−1.0 (3)	C12—P2—C61B—C62B	−172.6 (18)
P1—C21—C26—C25	−176.41 (18)	B1—P2—C61B—C62B	70 (2)
C61A—P2—C51A—C56A	55.0 (3)	C66B—C61B—C62B—C63B	−48 (2)
C51B—P2—C51A—C56A	22 (2)	P2—C61B—C62B—C63B	178.0 (16)
C61B—P2—C51A—C56A	59.8 (9)	C61B—C62B—C63B—C64B	51 (2)
C12—P2—C51A—C56A	173.8 (2)	C62B—C63B—C64B—C65B	−51 (2)
B1—P2—C51A—C56A	−68.1 (2)	C63B—C64B—C65B—C66B	51 (2)
C61A—P2—C51A—C52A	179.9 (2)	C64B—C65B—C66B—C61B	−56 (2)
C51B—P2—C51A—C52A	147 (2)	C62B—C61B—C66B—C65B	52 (2)
C61B—P2—C51A—C52A	−175.3 (9)	P2—C61B—C66B—C65B	−170.6 (14)
C12—P2—C51A—C52A	−61.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H7B···O1i	0.88 (7)	1.85 (7)	2.722 (4)	167 (6)
O2—H7A···O1	0.85 (5)	1.95 (5)	2.768 (4)	163 (5)
C51A—H51A···O1	1.00	2.28	3.083 (3)	136
C61A—H61A···O1	1.00	2.31	3.057 (5)	130

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H7B⋯O1i	0.88 (7)	1.85 (7)	2.722 (4)	167 (6)
O2—H7A⋯O1	0.85 (5)	1.95 (5)	2.768 (4)	163 (5)
C51A—H51A⋯O1	1.00	2.28	3.083 (3)	136
C61A—H61A⋯O1	1.00	2.31	3.057 (5)	130

Symmetry code: (i) .