Redetermination of trans-diaqua­tetra­methano­lcobalt(II) bis­(rac-1,1′-bi­naph­thalene-2,2′-diylphosphate) methanol disolvate monohydrate: a two-dimensional supra­molecular hydrogen-bonded network

In the title compound, trans-[Co(CH₃OH)₄(H₂O)₂](C₂₀H₁₂PO₄)₂·2CH₃OH·H₂O, the crystal packing shows a separation of the hydro­phobic naphthyl ring systems from the hydro­philic part of the structure, viz. the (RO)₂PO₂⁻ phosphate anion, the cobalt complex cation and the solvent mol­ecules. The binaphthyl tail-to-tail packing in the hydro­phobic layer is governed by weak C—H...π inter­actions. The present study performed at 203 K confirms the previous room-temperature study [McCann, Murphy, Cardin & Convery (1991), Polyhedron, 10, 2771–2777], but with improved precision. The centro­symmetric cobalt complex has very similar Co—O bond lengths and is isostructural with the trans-[Cu(H₂O)₂(CH₃OH)₄]²⁺ cation (which features a tetra­gonally compressed instead of the typical Jahn–Teller distorted elongated copper octa­hedron) in the isotypic copper(II) compound. The high degree of similarity in the Co and Cu structures shows the dominating effect of the hydrogen-bonding network on the metal coordination polyhedra. All H atoms of the Co and Cu aqua and methanol ligands are engaged in typical strong hydrogen-bonding inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 203 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.052
• wR factor = 0.147
• Data-to-parameter ratio = 14.2

checkCIF/PLATON results

No syntax errors found



Alert level G
PLAT794_ALERT_5_G Check Predicted Bond Valency for Co          (2)       2.13
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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
   1 ALERT type 5 Informative message, check

---

S1. Comment

In the structure of the title compound (I) one inversion-symmetrical trans-[Co(H₂O)₂(CH₃OH)₄]²⁺ cation is combined with two binaphthyl phosphate counterions, and one water and two methanol solvate molecules (McCann et al. 1991; Dorn et al., 2006). The packing of the title compound can be rationalized by a separation of the hydrophobic binaphthyl backbone from the hydrophilic (RO)₂PO₂^- phosphate groups, the cobalt complex cation and the solvent molecules into an inverse bilayer structure, as seen before (Wisser & Janiak, 2007; Dorn et al., 2006). The structure of (I) is isotypic to that of the copper(II) analogue where the expected normal Jahn-Teller distortion of an elongated octahedron is absent. Instead, a tetragonal compressed octahedron, indicative of a dynamic Jahn-Teller effect, is observed (Dorn et al., 2006). The M—O (M = Co and Cu) bonds lengths and their variations in the analogous structures are highly similar with M–O(H₂O) = 2.038 (3) and 1.937 (4) Å, and M–O(CH₃OH) = 2.089 (3)/2.104 (3) and 2.112 (4)/2.167 (4) Å for M = Co and Cu. The close similarity between the Co and Cu structures and the metal coordination polyhedra indicates a structure directing effect of the hydrogen-bonding interactions. For the Cu structure the two elongated Jahn-Teller-distorted states along the two trans-CH₃OH–Cu–CH₃OH bonds are of identical low energy and both occupied. There is no differentiation from any intermolecular interactions between these two states. The average of two tetragonally elongated octahedra then looks like a compressed octahedron for Cu (Deeth & Hearnshaw, 2006).

Fig. 1 shows a projection of the unit cell crystal packing to illustrate the layer-like arrangement of the hydrophobic and hydrophilic regions. The latter are also highlighted by the hydrogen-bonding network as red dashes (see Table for bond distances and angles). The interaction between the binaphthyl phosphate and the octahedrally coordinated cobalt(II) cation is visualized in Fig. 2. The binaphthyl tail-to-tail packing in the hydrophobic layer is governed by C–H^···π interactions (Dorn et al., 2006; Janiak, 2000; Nishio, 2004).

Related literature

For isotypic compounds and closely related structures, see: Deeth & Hearnshaw (2006); Dorn et al. (2006); Janiak (2000); McCann et al. (1991); Nishio (2004); Wisser & Janiak (2007).

S2. Experimental

A solution of racemic 1,1'-binaphthalene-2,2'-diyl phosphoric acid (139.2 mg, 0.20 mmol) (Dorn et al., 2006) in 12 ml of methanol was added to a solution of CoCl₂^.6H₂O (47.6 mg, 0.2 mmol) in 4 ml of distilled water. The solvent was slowly allowed to evaporate. After two days pink plates had formed which were separated by filtration. Crystal yield 96 mg, 48%. Analysis calculated for C₄₆H₅₄CoO₁₇P₂ (999.76): C 55.26, H 5.44; found: C 55.30, H 4.98. IR (KBr, ν cm^-1): 3209, 1653, 1617, 1587, 1506, 1464, 1430, 1328, 1236, 1208, 1093, 1068, 1022, 991, 960, 944, 868, 852, 816, 747, 719, 657, 580, 565, 532, 479, 415.

S3. Refinement

The previous room-temperature study (McCann et al. 1991; Refcode:KUPYID) converged with R(F) = 0.13 for 1577 unique reflections with I>2σ(I) that were collected up to 20°/θ. Cell parameters were a = 41.93 (3), b = 8.683 (2), c = 13.21 (1) Å, β = 105.41 (4)°. The low precision of the previous data was attributed to the smallness of the largest available crystals. No bond lengths or angles were given, neither in the original publication nor in the entry of the Cambridge Crystallographic Data base (message: No three-dimensional coordinates available). Our low-temperature structure redetermination gave improved cell parameters by a factor of 3–10. Data was collected to over θ = 26°, so that 2576 unique reflections with I>2σ(I) were available and the R factors improved considerably. H atoms bonded to C were refined with riding models and U_eq(H) = 1.2 U_eq(C_aromatic) or 1.5 U_eq(C_methyl), respectively. H atoms bonded to O atoms (H₂O, CH₃OH) were found from difference Fourier maps and their positions were freely refined with U_eq(H) = 1.2 U_eq(O_CH₃OH) and 1.5 U_eq(O_H₂O), respectively.

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Diamond (Crystal Impact, 2006); software used to prepare material for publication: publCIF (Westrip, 2007).

Figures

Fig. 1. : Projection of the crystal packing in compound (I) onto the (010) plane. Hydrogen bonds are indicated with red dashed lines. Displacement ellipsoids are drawn at the 50% probability level and H atoms are given as spheres of arbitrary radius.

Fig. 2. : Interaction between the 1,1'-binaphthalene-2,2'-diyl phosphate anion and the trans-diaqua-tetramethanol-cobalt(II) cation in compound (I). The cobalt cation is located on an inversion center. Hydrogen bonds are indicated with red dashed lines. Displacement ellipsoids are drawn at the 50% probability level and H atoms are given as spheres of arbitrary radius. Symmetry code: i =– x, 1 – y, – z.

trans-Diaquatetramethanolcobalt(II) bis(rac-1,1'-binaphthalene-2,2'-diylphosphate) methanol disolvate monohydrate

Crystal data

[Co(CH4O)4(H2O)2](C20H12PO4)2·2CH4O·H2O	F(000) = 2092
Mr = 999.76	Dx = 1.446 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 41.795 (9) Å	Cell parameters from 1024 reflections
b = 8.6674 (19) Å	θ = 2.4–20.0°
c = 13.161 (3) Å	µ = 0.52 mm^−1
β = 105.548 (4)°	T = 203 K
V = 4593.2 (18) Å^3	Plate, pink
Z = 4	0.49 × 0.26 × 0.02 mm

Data collection

Bruker APEX II CCD area-detector diffractometer	4506 independent reflections
Radiation source: fine-focus sealed tube	2576 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.085
\w scans	θmax = 26.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −51→51
Tmin = 0.786, Tmax = 0.988	k = −10→10
17662 measured reflections	l = −16→16

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.147	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ^2(Fo^2) + (0.0631P)^2 + 8.4598P] where P = (Fo^2 + 2Fc^2)/3
4506 reflections	(Δ/σ)max < 0.001
317 parameters	Δρmax = 0.53 e Å^−3
1 restraint	Δρmin = −0.57 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 F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > σ(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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
Co	0.0000	0.5000	0.5000	0.0259 (2)
O1	−0.02130 (8)	0.3144 (3)	0.5593 (2)	0.0382 (7)
H1D	−0.0282 (11)	0.320 (5)	0.618 (3)	0.046*
O2	0.02480 (8)	0.3480 (4)	0.4222 (3)	0.0421 (8)
H2D	0.0147 (12)	0.313 (6)	0.366 (4)	0.050*
O3	0.03873 (8)	0.5095 (4)	0.6325 (2)	0.0400 (8)
H3A	0.0530 (12)	0.587 (6)	0.645 (4)	0.060*
H3B	0.0410 (12)	0.444 (6)	0.682 (4)	0.060*
C1	−0.01939 (13)	0.1553 (5)	0.5351 (4)	0.0532 (14)
H1A	−0.0185	0.1445	0.4625	0.080*
H1B	−0.0388	0.1021	0.5446	0.080*
H1C	0.0005	0.1109	0.5817	0.080*
C2	0.05817 (12)	0.3240 (7)	0.4397 (4)	0.0681 (17)
H2A	0.0662	0.3815	0.3883	0.102*
H2B	0.0623	0.2149	0.4330	0.102*
H2C	0.0696	0.3585	0.5102	0.102*
P1	0.07186 (3)	0.84064 (12)	0.27597 (8)	0.0261 (3)
O4	0.09320 (6)	0.7848 (3)	0.1977 (2)	0.0278 (6)
O5	0.10030 (6)	0.8622 (3)	0.3853 (2)	0.0279 (6)
O6	0.04962 (7)	0.7097 (3)	0.2814 (2)	0.0308 (7)
O7	0.05750 (6)	0.9960 (3)	0.2485 (2)	0.0333 (7)
C3	0.15083 (9)	0.8126 (4)	0.2862 (3)	0.0229 (8)
C4	0.12404 (9)	0.8498 (4)	0.2035 (3)	0.0264 (9)
C5	0.12665 (10)	0.9437 (5)	0.1196 (3)	0.0311 (9)
H5	0.1079	0.9645	0.0633	0.037*
C6	0.15689 (10)	1.0049 (5)	0.1208 (3)	0.0347 (10)
H6	0.1590	1.0657	0.0638	0.042*
C7	0.18505 (10)	0.9783 (4)	0.2061 (3)	0.0308 (9)
C8	0.21623 (11)	1.0472 (5)	0.2093 (4)	0.0381 (11)
H8A	0.2184	1.1081	0.1525	0.046*
C9	0.24276 (11)	1.0259 (5)	0.2937 (4)	0.0432 (12)
H9A	0.2633	1.0715	0.2949	0.052*
C10	0.23970 (11)	0.9358 (5)	0.3792 (4)	0.0401 (11)
H10A	0.2581	0.9223	0.4379	0.048*
C11	0.21021 (10)	0.8677 (5)	0.3778 (3)	0.0322 (10)
H11	0.2086	0.8086	0.4361	0.039*
C12	0.18207 (9)	0.8835 (4)	0.2913 (3)	0.0256 (9)
C13	0.14619 (9)	0.7076 (4)	0.3716 (3)	0.0233 (8)
C14	0.12153 (10)	0.7362 (4)	0.4189 (3)	0.0258 (9)
C15	0.11689 (10)	0.6481 (5)	0.5036 (3)	0.0325 (10)
H15	0.0999	0.6733	0.5352	0.039*
C16	0.13723 (11)	0.5265 (5)	0.5390 (3)	0.0362 (10)
H16	0.1351	0.4710	0.5982	0.043*
C17	0.16142 (10)	0.4822 (4)	0.4885 (3)	0.0312 (9)
C18	0.18039 (11)	0.3463 (5)	0.5177 (4)	0.0397 (11)
H18	0.1781	0.2889	0.5760	0.048*
C19	0.20178 (12)	0.2974 (5)	0.4635 (4)	0.0465 (13)
H19	0.2138	0.2057	0.4836	0.056*
C20	0.20605 (11)	0.3825 (5)	0.3777 (4)	0.0409 (11)
H20	0.2209	0.3479	0.3401	0.049*
C21	0.18852 (10)	0.5168 (4)	0.3486 (3)	0.0320 (9)
H21	0.1916	0.5734	0.2911	0.038*
C22	0.16599 (9)	0.5716 (4)	0.4030 (3)	0.0255 (9)
O8	0.08231 (7)	0.7421 (3)	0.6938 (3)	0.0385 (8)
H8B	0.0747 (11)	0.826 (5)	0.702 (4)	0.046*
C23	0.11277 (12)	0.7125 (6)	0.7674 (4)	0.0559 (14)
H23A	0.1307	0.7326	0.7354	0.084*
H23B	0.1136	0.6054	0.7894	0.084*
H23C	0.1151	0.7789	0.8282	0.084*
O9	0.0000 (2)	0.1564 (4)	0.2500 (8)	0.0335 (9)
H9B	0.0193	0.0954	0.2435	0.050*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co	0.0305 (4)	0.0208 (4)	0.0277 (4)	−0.0006 (3)	0.0104 (3)	−0.0001 (3)
O1	0.058 (2)	0.0227 (15)	0.0414 (18)	−0.0052 (14)	0.0267 (16)	0.0016 (14)
O2	0.0330 (18)	0.049 (2)	0.045 (2)	−0.0008 (15)	0.0105 (15)	−0.0194 (16)
O3	0.050 (2)	0.0264 (17)	0.0384 (18)	−0.0094 (15)	0.0023 (15)	0.0069 (14)
C1	0.077 (4)	0.030 (3)	0.062 (3)	−0.001 (2)	0.035 (3)	−0.002 (2)
C2	0.043 (3)	0.096 (5)	0.063 (4)	0.017 (3)	0.010 (3)	−0.030 (3)
P1	0.0264 (6)	0.0216 (5)	0.0317 (6)	−0.0004 (4)	0.0102 (5)	−0.0011 (4)
O4	0.0237 (14)	0.0331 (15)	0.0264 (15)	−0.0022 (12)	0.0065 (12)	−0.0028 (12)
O5	0.0322 (15)	0.0231 (14)	0.0281 (15)	0.0023 (12)	0.0075 (12)	−0.0038 (12)
O6	0.0321 (16)	0.0269 (15)	0.0356 (16)	−0.0092 (12)	0.0131 (13)	−0.0031 (12)
O7	0.0267 (15)	0.0246 (15)	0.0483 (18)	0.0058 (12)	0.0095 (13)	0.0076 (14)
C3	0.026 (2)	0.0181 (19)	0.025 (2)	0.0021 (16)	0.0088 (17)	−0.0019 (16)
C4	0.026 (2)	0.025 (2)	0.031 (2)	0.0027 (17)	0.0129 (18)	−0.0021 (17)
C5	0.031 (2)	0.030 (2)	0.033 (2)	0.0070 (18)	0.0102 (19)	0.0022 (18)
C6	0.041 (3)	0.029 (2)	0.039 (2)	0.007 (2)	0.020 (2)	0.007 (2)
C7	0.034 (2)	0.026 (2)	0.037 (2)	0.0030 (18)	0.0168 (19)	−0.0012 (18)
C8	0.038 (3)	0.035 (2)	0.048 (3)	−0.007 (2)	0.023 (2)	−0.003 (2)
C9	0.031 (2)	0.043 (3)	0.058 (3)	−0.011 (2)	0.017 (2)	−0.013 (2)
C10	0.030 (2)	0.037 (3)	0.052 (3)	−0.002 (2)	0.008 (2)	−0.009 (2)
C11	0.034 (2)	0.026 (2)	0.035 (2)	−0.0004 (18)	0.0076 (19)	−0.0025 (18)
C12	0.025 (2)	0.0181 (19)	0.034 (2)	0.0017 (16)	0.0088 (18)	−0.0029 (17)
C13	0.027 (2)	0.0177 (19)	0.023 (2)	−0.0013 (16)	0.0031 (17)	−0.0012 (15)
C14	0.030 (2)	0.021 (2)	0.026 (2)	0.0000 (17)	0.0053 (18)	0.0007 (16)
C15	0.036 (2)	0.038 (2)	0.026 (2)	−0.004 (2)	0.0128 (19)	0.0024 (19)
C16	0.045 (3)	0.035 (3)	0.028 (2)	−0.009 (2)	0.010 (2)	0.0058 (19)
C17	0.031 (2)	0.024 (2)	0.033 (2)	−0.0059 (18)	−0.0002 (18)	0.0045 (18)
C18	0.040 (3)	0.026 (2)	0.047 (3)	−0.004 (2)	0.000 (2)	0.013 (2)
C19	0.043 (3)	0.022 (2)	0.066 (3)	0.005 (2)	0.000 (3)	0.005 (2)
C20	0.037 (3)	0.025 (2)	0.058 (3)	0.0079 (19)	0.006 (2)	−0.005 (2)
C21	0.030 (2)	0.023 (2)	0.041 (2)	−0.0015 (18)	0.0060 (19)	0.0003 (19)
C22	0.022 (2)	0.0192 (19)	0.032 (2)	−0.0039 (16)	0.0027 (18)	−0.0001 (17)
O8	0.0364 (18)	0.0285 (17)	0.0480 (19)	0.0082 (13)	0.0069 (15)	0.0007 (15)
C23	0.044 (3)	0.071 (4)	0.051 (3)	0.017 (3)	0.008 (3)	0.012 (3)
O9	0.028 (2)	0.027 (2)	0.047 (3)	0.000	0.0125 (19)	0.000

Geometric parameters (Å, º)

Co—O3	2.038 (3)	C7—C8	1.424 (6)
Co—O3^i	2.038 (3)	C8—C9	1.355 (6)
Co—O1	2.089 (3)	C8—H8A	0.9400
Co—O1^i	2.089 (3)	C9—C10	1.404 (6)
Co—O2	2.104 (3)	C9—H9A	0.9400
Co—O2^i	2.104 (3)	C10—C11	1.362 (6)
O1—C1	1.422 (5)	C10—H10A	0.9400
O1—H1D	0.90 (3)	C11—C12	1.407 (5)
O2—C2	1.367 (5)	C11—H11	0.9400
O2—H2D	0.80 (5)	C13—C14	1.362 (5)
O3—H3A	0.88 (5)	C13—C22	1.435 (5)
O3—H3B	0.85 (5)	C14—C15	1.407 (5)
C1—H1A	0.9700	C15—C16	1.356 (6)
C1—H1B	0.9700	C15—H15	0.9400
C1—H1C	0.9700	C16—C17	1.404 (6)
C2—H2A	0.9700	C16—H16	0.9400
C2—H2B	0.9700	C17—C18	1.414 (6)
C2—H2C	0.9700	C17—C22	1.420 (5)
P1—O7	1.479 (3)	C18—C19	1.353 (7)
P1—O6	1.481 (3)	C18—H18	0.9400
P1—O4	1.607 (3)	C19—C20	1.400 (6)
P1—O5	1.613 (3)	C19—H19	0.9400
O4—C4	1.389 (4)	C20—C21	1.374 (5)
O5—C14	1.402 (4)	C20—H20	0.9400
C3—C4	1.375 (5)	C21—C22	1.410 (5)
C3—C12	1.429 (5)	C21—H21	0.9400
C3—C13	1.498 (5)	O8—C23	1.401 (5)
C4—C5	1.400 (5)	O8—H8B	0.81 (5)
C5—C6	1.367 (6)	C23—H23A	0.9700
C5—H5	0.9400	C23—H23B	0.9700
C6—C7	1.411 (6)	C23—H23C	0.9700
C6—H6	0.9400	O9—H9B	0.9881
C7—C12	1.422 (5)
O3—Co—O3^i	180.00 (16)	C6—C7—C12	119.4 (4)
O3—Co—O1	91.81 (13)	C6—C7—C8	121.1 (4)
O3^i—Co—O1	88.19 (13)	C12—C7—C8	119.5 (4)
O3—Co—O1^i	88.19 (13)	C9—C8—C7	120.5 (4)
O3^i—Co—O1^i	91.81 (13)	C9—C8—H8A	119.7
O1—Co—O1^i	180.00 (17)	C7—C8—H8A	119.7
O3—Co—O2	93.42 (13)	C8—C9—C10	120.2 (4)
O3^i—Co—O2	86.58 (13)	C8—C9—H9A	119.9
O1—Co—O2	90.83 (12)	C10—C9—H9A	119.9
O1^i—Co—O2	89.17 (12)	C11—C10—C9	120.4 (4)
O3—Co—O2^i	86.58 (13)	C11—C10—H10A	119.8
O3^i—Co—O2^i	93.42 (13)	C9—C10—H10A	119.8
O1—Co—O2^i	89.17 (12)	C10—C11—C12	121.8 (4)
O1^i—Co—O2^i	90.83 (12)	C10—C11—H11	119.1
O2—Co—O2^i	180.00 (16)	C12—C11—H11	119.1
C1—O1—Co	127.4 (3)	C11—C12—C7	117.6 (4)
C1—O1—H1D	107 (3)	C11—C12—C3	123.5 (4)
Co—O1—H1D	123 (3)	C7—C12—C3	118.9 (4)
C2—O2—Co	128.8 (3)	C14—C13—C22	117.8 (3)
C2—O2—H2D	111 (4)	C14—C13—C3	119.8 (3)
Co—O2—H2D	118 (4)	C22—C13—C3	122.3 (3)
Co—O3—H3A	122 (3)	C13—C14—O5	119.4 (3)
Co—O3—H3B	122 (3)	C13—C14—C15	123.0 (4)
H3A—O3—H3B	116 (5)	O5—C14—C15	117.5 (3)
O1—C1—H1A	109.5	C16—C15—C14	119.2 (4)
O1—C1—H1B	109.5	C16—C15—H15	120.4
H1A—C1—H1B	109.5	C14—C15—H15	120.4
O1—C1—H1C	109.5	C15—C16—C17	121.0 (4)
H1A—C1—H1C	109.5	C15—C16—H16	119.5
H1B—C1—H1C	109.5	C17—C16—H16	119.5
O2—C2—H2A	109.5	C16—C17—C18	121.4 (4)
O2—C2—H2B	109.5	C16—C17—C22	119.5 (4)
H2A—C2—H2B	109.5	C18—C17—C22	119.0 (4)
O2—C2—H2C	109.5	C19—C18—C17	121.3 (4)
H2A—C2—H2C	109.5	C19—C18—H18	119.4
H2B—C2—H2C	109.5	C17—C18—H18	119.4
O7—P1—O6	119.39 (16)	C18—C19—C20	120.3 (4)
O7—P1—O4	112.08 (16)	C18—C19—H19	119.8
O6—P1—O4	105.30 (15)	C20—C19—H19	119.8
O7—P1—O5	105.46 (15)	C21—C20—C19	119.8 (4)
O6—P1—O5	111.56 (15)	C21—C20—H20	120.1
O4—P1—O5	101.75 (14)	C19—C20—H20	120.1
C4—O4—P1	120.6 (2)	C20—C21—C22	121.5 (4)
C14—O5—P1	116.4 (2)	C20—C21—H21	119.2
C4—C3—C12	118.5 (3)	C22—C21—H21	119.2
C4—C3—C13	119.6 (3)	C21—C22—C17	117.9 (4)
C12—C3—C13	121.8 (3)	C21—C22—C13	122.8 (4)
C3—C4—O4	119.7 (3)	C17—C22—C13	119.1 (4)
C3—C4—C5	122.8 (4)	C23—O8—H8B	113 (3)
O4—C4—C5	117.4 (4)	O8—C23—H23A	109.5
C6—C5—C4	118.9 (4)	O8—C23—H23B	109.5
C6—C5—H5	120.5	H23A—C23—H23B	109.5
C4—C5—H5	120.5	O8—C23—H23C	109.5
C5—C6—C7	121.1 (4)	H23A—C23—H23C	109.5
C5—C6—H6	119.4	H23B—C23—H23C	109.5
C7—C6—H6	119.4

Symmetry code: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1D···O6^i	0.90 (3)	1.80 (4)	2.677 (4)	164 (4)
O2—H2D···O9	0.80 (5)	2.02 (5)	2.777 (7)	158 (5)
O3—H3A···O8	0.88 (5)	1.82 (5)	2.692 (4)	170 (5)
O3—H3B···O6^ii	0.85 (5)	1.83 (5)	2.679 (4)	172 (5)
O8—H8B···O7^iii	0.81 (5)	1.87 (5)	2.673 (4)	168 (5)
O9—H9B···O7^iv	0.99	1.80	2.781 (9)	172.1

Symmetry codes: (i) −x, −y+1, −z+1; (ii) x, −y+1, z+1/2; (iii) x, −y+2, z+1/2; (iv) x, y−1, z.