Crystal structure of [bis­(2,6-diiso­propyl­phen­yl) phosphato-κO]tris­(methanol-κO)lithium methanol monosolvate

In the first reported crystal structure of the family of lithium phosphate diesters, the Li atom is in a slightly distorted tetra­hedral coordination environment and exhibits one intra­molecular O—H...O hydrogen bond between a coordinating methanol mol­ecule and the terminal non-coordinating O atom of the phosphate group. The unit is connected with two non-coordinating methanol mol­ecules through two inter­molecular O—H...O hydrogen bonds and with a neighbouring unit through two other O—H...O inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 123 K
• Mean [sigma](C-C) = 0.002 Å
• Disorder in main residue
• R factor = 0.040
• wR factor = 0.112
• Data-to-parameter ratio = 27.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent  C     Ueq(max)/Ueq(min) Range        3.4 Ratio

Alert level G
PLAT300_ALERT_4_G Atom Site Occupancy of >C29A   is Constrained at      0.750 Check
PLAT300_ALERT_4_G Atom Site Occupancy of <C29B   is Constrained at      0.250 Check
PLAT301_ALERT_3_G Main Residue  Disorder ............ Percentage =          3 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Th(Min) ...          1 Report
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         13 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   5 ALERT level G = General information/check it is not something unexpected

   0 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
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010).

[Bis(2,6-diisopropylphenyl) phosphato-κO]tris(methanol-κO)lithium methanol monosolvate

Crystal data

[Li(C24H34O4P)(CH4O)3]·CH4O	Z = 2
Mr = 552.59	F(000) = 600
Triclinic, P1	Dx = 1.160 Mg m^−3
a = 11.1853 (6) Å	Mo Kα radiation, λ = 0.710730 (9) Å
b = 11.5046 (6) Å	Cell parameters from 9855 reflections
c = 14.5237 (7) Å	θ = 2.3–31.3°
α = 90.855 (2)°	µ = 0.13 mm^−1
β = 102.859 (2)°	T = 123 K
γ = 118.683 (1)°	Needle, colorless
V = 1582.21 (14) Å^3	0.60 × 0.20 × 0.10 mm

Data collection

Bruker APEXII CCD area-detector diffractometer	10353 independent reflections
Radiation source: fine-focus sealed tube	8544 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
ω scans	θmax = 31.3°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −16→16
Tmin = 0.872, Tmax = 0.986	k = −16→16
22920 measured reflections	l = −21→21

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)] = 0.040	Hydrogen site location: mixed
wR(F^2) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0628P)^2 + 0.329P] where P = (Fo^2 + 2Fc^2)/3
10353 reflections	(Δ/σ)max = 0.001
382 parameters	Δρmax = 0.77 e Å^−3
0 restraints	Δρmin = −0.53 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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
P1	0.62300 (2)	0.88864 (2)	0.82666 (2)	0.01132 (6)
Li1	0.7224 (2)	1.0298 (2)	1.03455 (14)	0.0216 (4)
O1	0.71418 (7)	0.82744 (7)	0.85725 (5)	0.01552 (14)
O2	0.64407 (7)	0.99757 (7)	0.89696 (5)	0.01510 (13)
O3	0.63126 (7)	0.93432 (7)	0.72374 (5)	0.01310 (13)
O4	0.45827 (7)	0.78087 (7)	0.80228 (5)	0.01346 (13)
C1	0.75457 (9)	0.99858 (9)	0.69226 (6)	0.01272 (16)
C2	0.82677 (10)	1.13862 (9)	0.70219 (7)	0.01421 (17)
C3	0.94480 (11)	1.19980 (10)	0.66505 (7)	0.01713 (18)
H3A	0.9972	1.2947	0.6711	0.021*
C4	0.98609 (11)	1.12365 (10)	0.61952 (7)	0.01835 (19)
H4A	1.0670	1.1667	0.5954	0.022*
C5	0.90964 (11)	0.98439 (10)	0.60897 (7)	0.01706 (18)
H5A	0.9383	0.9336	0.5767	0.020*
C6	0.79173 (10)	0.91821 (9)	0.64503 (7)	0.01379 (17)
C7	0.78093 (11)	1.22290 (10)	0.75072 (7)	0.01677 (18)
H7A	0.6876	1.1609	0.7628	0.020*
C8	0.76209 (14)	1.32155 (12)	0.68757 (9)	0.0267 (2)
H8A	0.6950	1.2724	0.6260	0.040*
H8B	0.8533	1.3862	0.6772	0.040*
H8C	0.7259	1.3691	0.7191	0.040*
C9	0.88650 (13)	1.29710 (11)	0.84741 (8)	0.0234 (2)
H9A	0.8916	1.2320	0.8885	0.035*
H9B	0.8554	1.3507	0.8777	0.035*
H9C	0.9800	1.3561	0.8377	0.035*
C10	0.70174 (10)	0.76631 (10)	0.62834 (7)	0.01561 (17)
H10A	0.6566	0.7390	0.6823	0.019*
C11	0.78739 (13)	0.69543 (11)	0.62659 (9)	0.0243 (2)
H11A	0.8629	0.7261	0.6858	0.036*
H11B	0.8287	0.7163	0.5721	0.036*
H11C	0.7253	0.5985	0.6207	0.036*
C12	0.58316 (12)	0.72179 (11)	0.53609 (8)	0.0228 (2)
H12A	0.5282	0.7665	0.5397	0.034*
H12B	0.5212	0.6246	0.5281	0.034*
H12C	0.6242	0.7459	0.4816	0.034*
C13	0.37172 (10)	0.70309 (9)	0.71375 (7)	0.01358 (16)
C14	0.30293 (10)	0.75513 (10)	0.64912 (7)	0.01566 (17)
C15	0.20879 (11)	0.67082 (11)	0.56457 (7)	0.01988 (19)
H15A	0.1599	0.7025	0.5193	0.024*
C16	0.18558 (11)	0.54178 (11)	0.54579 (8)	0.0221 (2)
H16A	0.1214	0.4862	0.4881	0.027*
C17	0.25624 (11)	0.49414 (10)	0.61134 (8)	0.02018 (19)
H17A	0.2401	0.4060	0.5977	0.024*
C18	0.35065 (10)	0.57348 (10)	0.69699 (7)	0.01573 (17)
C19	0.32711 (11)	0.89620 (10)	0.66694 (7)	0.01742 (18)
H19A	0.3980	0.9406	0.7299	0.021*
C20	0.19082 (13)	0.89471 (14)	0.67174 (9)	0.0277 (2)
H20A	0.1560	0.8457	0.7232	0.042*
H20B	0.1194	0.8506	0.6109	0.042*
H20C	0.2100	0.9868	0.6842	0.042*
C21	0.38705 (12)	0.97881 (12)	0.58994 (8)	0.0239 (2)
H21A	0.4731	0.9779	0.5866	0.036*
H21B	0.4093	1.0713	0.6061	0.036*
H21C	0.3170	0.9400	0.5280	0.036*
C22	0.42568 (11)	0.52122 (10)	0.77067 (7)	0.01739 (18)
H22A	0.5211	0.5984	0.8025	0.021*
C23	0.44768 (15)	0.41384 (12)	0.72666 (9)	0.0283 (2)
H23A	0.4917	0.4461	0.6742	0.042*
H23B	0.3563	0.3322	0.7022	0.042*
H23C	0.5092	0.3944	0.7754	0.042*
C24	0.34634 (14)	0.46943 (14)	0.84766 (9)	0.0294 (3)
H24A	0.3386	0.5414	0.8779	0.044*
H24B	0.3981	0.4396	0.8959	0.044*
H24C	0.2516	0.3941	0.8185	0.044*
O5	0.81065 (10)	0.91990 (11)	1.04939 (6)	0.0312 (2)
C25	0.92769 (13)	0.92434 (13)	1.11483 (9)	0.0284 (2)
H25A	0.9020	0.8346	1.1315	0.043*
H25B	0.9552	0.9860	1.1726	0.043*
H25C	1.0070	0.9554	1.0857	0.043*
O6	0.86571 (9)	1.20747 (8)	1.09305 (6)	0.02504 (17)
C27	0.84869 (16)	1.31713 (13)	1.11945 (11)	0.0339 (3)
H27A	0.8725	1.3800	1.0729	0.051*
H27B	0.9113	1.3628	1.1829	0.051*
H27C	0.7505	1.2842	1.1207	0.051*
O7	0.56431 (9)	0.94990 (8)	1.09033 (6)	0.02329 (17)
C29A	0.5209 (6)	0.8252 (4)	1.1245 (4)	0.0311 (8)	0.75 (2)
H29A	0.5812	0.7894	1.1136	0.047*	0.75 (2)
H29B	0.4225	0.7624	1.0905	0.047*	0.75 (2)
H29C	0.5290	0.8372	1.1929	0.047*	0.75 (2)
C29B	0.4900 (14)	0.8055 (11)	1.084 (2)	0.044 (3)	0.25 (2)
H29D	0.4135	0.7671	1.0245	0.066*	0.25 (2)
H29E	0.4504	0.7794	1.1384	0.066*	0.25 (2)
H29F	0.5558	0.7723	1.0829	0.066*	0.25 (2)
O8	0.85286 (11)	0.68825 (11)	0.87815 (8)	0.0382 (2)
C31	0.78917 (14)	0.59808 (13)	0.93888 (10)	0.0308 (3)
H31A	0.7034	0.5192	0.9011	0.046*
H31B	0.7646	0.6413	0.9843	0.046*
H31C	0.8550	0.5706	0.9738	0.046*
H26	0.799 (2)	0.8875 (19)	0.9979 (15)	0.045 (5)*
H28	0.953 (2)	1.236 (2)	1.0986 (14)	0.051 (5)*
H30	0.507 (2)	0.9752 (19)	1.0954 (14)	0.049 (5)*
H32	0.814 (2)	0.7331 (19)	0.8674 (14)	0.047 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.01157 (11)	0.01212 (11)	0.01118 (11)	0.00666 (8)	0.00276 (8)	0.00173 (8)
Li1	0.0244 (9)	0.0239 (9)	0.0188 (8)	0.0142 (8)	0.0046 (7)	0.0014 (7)
O1	0.0157 (3)	0.0174 (3)	0.0161 (3)	0.0110 (3)	0.0025 (3)	0.0020 (3)
O2	0.0175 (3)	0.0154 (3)	0.0139 (3)	0.0094 (3)	0.0039 (2)	0.0008 (2)
O3	0.0117 (3)	0.0157 (3)	0.0126 (3)	0.0066 (2)	0.0048 (2)	0.0041 (2)
O4	0.0119 (3)	0.0149 (3)	0.0119 (3)	0.0055 (2)	0.0028 (2)	0.0017 (2)
C1	0.0109 (4)	0.0150 (4)	0.0121 (4)	0.0060 (3)	0.0034 (3)	0.0024 (3)
C2	0.0147 (4)	0.0143 (4)	0.0132 (4)	0.0070 (3)	0.0033 (3)	0.0018 (3)
C3	0.0159 (4)	0.0147 (4)	0.0177 (4)	0.0052 (3)	0.0048 (3)	0.0021 (3)
C4	0.0145 (4)	0.0194 (5)	0.0195 (5)	0.0059 (4)	0.0075 (3)	0.0031 (4)
C5	0.0160 (4)	0.0196 (4)	0.0168 (4)	0.0091 (4)	0.0060 (3)	0.0016 (3)
C6	0.0135 (4)	0.0149 (4)	0.0126 (4)	0.0070 (3)	0.0028 (3)	0.0013 (3)
C7	0.0202 (4)	0.0146 (4)	0.0178 (4)	0.0098 (4)	0.0064 (4)	0.0027 (3)
C8	0.0362 (6)	0.0272 (6)	0.0286 (6)	0.0231 (5)	0.0124 (5)	0.0112 (4)
C9	0.0284 (5)	0.0191 (5)	0.0205 (5)	0.0106 (4)	0.0056 (4)	−0.0021 (4)
C10	0.0174 (4)	0.0139 (4)	0.0160 (4)	0.0077 (4)	0.0056 (3)	0.0008 (3)
C11	0.0265 (5)	0.0194 (5)	0.0326 (6)	0.0147 (4)	0.0100 (4)	0.0039 (4)
C12	0.0221 (5)	0.0180 (5)	0.0215 (5)	0.0068 (4)	0.0008 (4)	−0.0004 (4)
C13	0.0107 (4)	0.0145 (4)	0.0132 (4)	0.0044 (3)	0.0034 (3)	0.0021 (3)
C14	0.0131 (4)	0.0188 (4)	0.0152 (4)	0.0079 (4)	0.0040 (3)	0.0045 (3)
C15	0.0155 (4)	0.0248 (5)	0.0167 (4)	0.0092 (4)	0.0012 (3)	0.0041 (4)
C16	0.0174 (5)	0.0225 (5)	0.0180 (5)	0.0051 (4)	0.0005 (4)	0.0000 (4)
C17	0.0183 (4)	0.0157 (4)	0.0198 (5)	0.0043 (4)	0.0025 (4)	0.0003 (4)
C18	0.0139 (4)	0.0148 (4)	0.0163 (4)	0.0053 (3)	0.0044 (3)	0.0035 (3)
C19	0.0170 (4)	0.0208 (5)	0.0179 (4)	0.0123 (4)	0.0039 (3)	0.0044 (4)
C20	0.0249 (5)	0.0372 (6)	0.0314 (6)	0.0226 (5)	0.0089 (5)	0.0077 (5)
C21	0.0248 (5)	0.0250 (5)	0.0236 (5)	0.0137 (4)	0.0062 (4)	0.0105 (4)
C22	0.0187 (4)	0.0143 (4)	0.0184 (4)	0.0078 (4)	0.0040 (4)	0.0037 (3)
C23	0.0388 (7)	0.0247 (5)	0.0270 (6)	0.0213 (5)	0.0058 (5)	0.0031 (4)
C24	0.0357 (6)	0.0361 (6)	0.0252 (6)	0.0215 (6)	0.0146 (5)	0.0156 (5)
O5	0.0379 (5)	0.0508 (6)	0.0161 (4)	0.0356 (5)	−0.0045 (3)	−0.0052 (4)
C25	0.0228 (5)	0.0342 (6)	0.0244 (5)	0.0151 (5)	−0.0029 (4)	0.0048 (5)
O6	0.0241 (4)	0.0222 (4)	0.0292 (4)	0.0115 (3)	0.0080 (3)	−0.0014 (3)
C27	0.0407 (7)	0.0261 (6)	0.0443 (8)	0.0197 (6)	0.0210 (6)	0.0057 (5)
O7	0.0300 (4)	0.0268 (4)	0.0267 (4)	0.0213 (4)	0.0144 (3)	0.0105 (3)
C29A	0.0370 (16)	0.0231 (11)	0.0440 (17)	0.0190 (11)	0.0200 (14)	0.0109 (11)
C29B	0.034 (4)	0.026 (4)	0.080 (11)	0.017 (3)	0.025 (5)	0.013 (5)
O8	0.0365 (5)	0.0451 (6)	0.0568 (7)	0.0329 (5)	0.0243 (5)	0.0282 (5)
C31	0.0285 (6)	0.0269 (6)	0.0361 (7)	0.0144 (5)	0.0046 (5)	0.0098 (5)

Geometric parameters (Å, º)

P1—O1	1.4934 (7)	C16—H16A	0.9500
P1—O2	1.4965 (7)	C17—C18	1.3971 (14)
P1—O3	1.5993 (7)	C17—H17A	0.9500
P1—O4	1.6003 (7)	C18—C22	1.5214 (14)
Li1—O2	1.945 (2)	C19—C20	1.5335 (15)
Li1—O5	1.932 (2)	C19—C21	1.5352 (15)
Li1—O6	1.915 (2)	C19—H19A	1.0000
Li1—O7	1.931 (2)	C20—H20A	0.9800
O3—C1	1.4035 (11)	C20—H20B	0.9800
O4—C13	1.4040 (11)	C20—H20C	0.9800
C1—C2	1.4003 (13)	C21—H21A	0.9800
C1—C6	1.4053 (13)	C21—H21B	0.9800
C2—C3	1.4019 (13)	C21—H21C	0.9800
C2—C7	1.5224 (13)	C22—C23	1.5276 (15)
C3—C4	1.3875 (14)	C22—C24	1.5320 (15)
C3—H3A	0.9500	C22—H22A	1.0000
C4—C5	1.3930 (14)	C23—H23A	0.9800
C4—H4A	0.9500	C23—H23B	0.9800
C5—C6	1.3960 (13)	C23—H23C	0.9800
C5—H5A	0.9500	C24—H24A	0.9800
C6—C10	1.5219 (13)	C24—H24B	0.9800
C7—C8	1.5325 (15)	C24—H24C	0.9800
C7—C9	1.5342 (15)	O5—C25	1.4144 (14)
C7—H7A	1.0000	O5—H26	0.79 (2)
C8—H8A	0.9800	C25—H25A	0.9800
C8—H8B	0.9800	C25—H25B	0.9800
C8—H8C	0.9800	C25—H25C	0.9800
C9—H9A	0.9800	O6—C27	1.4225 (14)
C9—H9B	0.9800	O6—H28	0.85 (2)
C9—H9C	0.9800	C27—H27A	0.9800
C10—C11	1.5309 (14)	C27—H27B	0.9800
C10—C12	1.5339 (15)	C27—H27C	0.9800
C10—H10A	1.0000	O7—C29A	1.415 (3)
C11—H11A	0.9800	O7—C29B	1.447 (11)
C11—H11B	0.9800	O7—H30	0.83 (2)
C11—H11C	0.9800	C29A—H29A	0.9800
C12—H12A	0.9800	C29A—H29B	0.9800
C12—H12B	0.9800	C29A—H29C	0.9800
C12—H12C	0.9800	C29B—H29D	0.9800
C13—C18	1.4016 (14)	C29B—H29E	0.9800
C13—C14	1.4032 (13)	C29B—H29F	0.9800
C14—C15	1.4021 (14)	O8—C31	1.3996 (16)
C14—C19	1.5196 (14)	O8—H32	0.82 (2)
C15—C16	1.3901 (16)	C31—H31A	0.9800
C15—H15A	0.9500	C31—H31B	0.9800
C16—C17	1.3885 (15)	C31—H31C	0.9800
O1—P1—O2	115.86 (4)	C18—C17—H17A	119.4
O1—P1—O3	110.98 (4)	C17—C18—C13	117.37 (9)
O2—P1—O3	111.66 (4)	C17—C18—C22	121.75 (9)
O1—P1—O4	112.44 (4)	C13—C18—C22	120.87 (9)
O2—P1—O4	105.46 (4)	C14—C19—C20	111.38 (9)
O3—P1—O4	99.06 (4)	C14—C19—C21	111.12 (9)
O6—Li1—O7	114.81 (10)	C20—C19—C21	110.04 (9)
O6—Li1—O5	106.80 (10)	C14—C19—H19A	108.1
O7—Li1—O5	107.49 (10)	C20—C19—H19A	108.1
O6—Li1—O2	118.40 (11)	C21—C19—H19A	108.1
O7—Li1—O2	106.73 (10)	C19—C20—H20A	109.5
O5—Li1—O2	101.32 (9)	C19—C20—H20B	109.5
P1—O2—Li1	128.08 (7)	H20A—C20—H20B	109.5
C1—O3—P1	125.61 (6)	C19—C20—H20C	109.5
C13—O4—P1	126.90 (6)	H20A—C20—H20C	109.5
C2—C1—O3	118.35 (8)	H20B—C20—H20C	109.5
C2—C1—C6	123.54 (9)	C19—C21—H21A	109.5
O3—C1—C6	117.87 (8)	C19—C21—H21B	109.5
C1—C2—C3	117.12 (9)	H21A—C21—H21B	109.5
C1—C2—C7	122.36 (9)	C19—C21—H21C	109.5
C3—C2—C7	120.52 (9)	H21A—C21—H21C	109.5
C4—C3—C2	120.88 (9)	H21B—C21—H21C	109.5
C4—C3—H3A	119.6	C18—C22—C23	113.01 (9)
C2—C3—H3A	119.6	C18—C22—C24	110.50 (9)
C3—C4—C5	120.38 (9)	C23—C22—C24	110.65 (9)
C3—C4—H4A	119.8	C18—C22—H22A	107.5
C5—C4—H4A	119.8	C23—C22—H22A	107.5
C4—C5—C6	121.16 (9)	C24—C22—H22A	107.5
C4—C5—H5A	119.4	C22—C23—H23A	109.5
C6—C5—H5A	119.4	C22—C23—H23B	109.5
C5—C6—C1	116.89 (9)	H23A—C23—H23B	109.5
C5—C6—C10	121.63 (8)	C22—C23—H23C	109.5
C1—C6—C10	121.37 (8)	H23A—C23—H23C	109.5
C2—C7—C8	111.88 (8)	H23B—C23—H23C	109.5
C2—C7—C9	110.51 (8)	C22—C24—H24A	109.5
C8—C7—C9	110.68 (9)	C22—C24—H24B	109.5
C2—C7—H7A	107.9	H24A—C24—H24B	109.5
C8—C7—H7A	107.9	C22—C24—H24C	109.5
C9—C7—H7A	107.9	H24A—C24—H24C	109.5
C7—C8—H8A	109.5	H24B—C24—H24C	109.5
C7—C8—H8B	109.5	C25—O5—Li1	135.51 (10)
H8A—C8—H8B	109.5	C25—O5—H26	111.9 (14)
C7—C8—H8C	109.5	Li1—O5—H26	106.6 (14)
H8A—C8—H8C	109.5	O5—C25—H25A	109.5
H8B—C8—H8C	109.5	O5—C25—H25B	109.5
C7—C9—H9A	109.5	H25A—C25—H25B	109.5
C7—C9—H9B	109.5	O5—C25—H25C	109.5
H9A—C9—H9B	109.5	H25A—C25—H25C	109.5
C7—C9—H9C	109.5	H25B—C25—H25C	109.5
H9A—C9—H9C	109.5	C27—O6—Li1	128.27 (10)
H9B—C9—H9C	109.5	C27—O6—H28	108.3 (14)
C6—C10—C11	113.23 (8)	Li1—O6—H28	122.7 (13)
C6—C10—C12	109.69 (8)	O6—C27—H27A	109.5
C11—C10—C12	110.98 (9)	O6—C27—H27B	109.5
C6—C10—H10A	107.6	H27A—C27—H27B	109.5
C11—C10—H10A	107.6	O6—C27—H27C	109.5
C12—C10—H10A	107.6	H27A—C27—H27C	109.5
C10—C11—H11A	109.5	H27B—C27—H27C	109.5
C10—C11—H11B	109.5	C29A—O7—Li1	122.16 (15)
H11A—C11—H11B	109.5	C29B—O7—Li1	117.0 (7)
C10—C11—H11C	109.5	C29A—O7—H30	108.0 (14)
H11A—C11—H11C	109.5	C29B—O7—H30	106.9 (14)
H11B—C11—H11C	109.5	Li1—O7—H30	129.6 (14)
C10—C12—H12A	109.5	O7—C29A—H29A	109.5
C10—C12—H12B	109.5	O7—C29A—H29B	109.5
H12A—C12—H12B	109.5	H29A—C29A—H29B	109.5
C10—C12—H12C	109.5	O7—C29A—H29C	109.5
H12A—C12—H12C	109.5	H29A—C29A—H29C	109.5
H12B—C12—H12C	109.5	H29B—C29A—H29C	109.5
C18—C13—C14	123.15 (9)	O7—C29B—H29D	109.5
C18—C13—O4	118.19 (8)	O7—C29B—H29E	109.5
C14—C13—O4	118.51 (8)	H29D—C29B—H29E	109.5
C15—C14—C13	117.02 (9)	O7—C29B—H29F	109.5
C15—C14—C19	119.91 (9)	H29D—C29B—H29F	109.5
C13—C14—C19	123.07 (9)	H29E—C29B—H29F	109.5
C16—C15—C14	121.25 (10)	C31—O8—H32	108.1 (14)
C16—C15—H15A	119.4	O8—C31—H31A	109.5
C14—C15—H15A	119.4	O8—C31—H31B	109.5
C17—C16—C15	120.01 (10)	H31A—C31—H31B	109.5
C17—C16—H16A	120.0	O8—C31—H31C	109.5
C15—C16—H16A	120.0	H31A—C31—H31C	109.5
C16—C17—C18	121.20 (10)	H31B—C31—H31C	109.5
C16—C17—H17A	119.4
O1—P1—O2—Li1	−22.98 (11)	C3—C2—C7—C9	−70.95 (12)
O3—P1—O2—Li1	−151.34 (9)	C5—C6—C10—C11	34.55 (13)
O4—P1—O2—Li1	102.06 (10)	C1—C6—C10—C11	−149.58 (9)
O1—P1—O3—C1	−42.03 (8)	C5—C6—C10—C12	−90.02 (11)
O2—P1—O3—C1	88.89 (8)	C1—C6—C10—C12	85.85 (11)
O4—P1—O3—C1	−160.39 (7)	P1—O4—C13—C18	95.20 (10)
Li1—P1—O3—C1	68.81 (10)	P1—O4—C13—C14	−89.13 (10)
O1—P1—O4—C13	−88.42 (8)	C18—C13—C14—C15	0.30 (14)
O2—P1—O4—C13	144.44 (7)	O4—C13—C14—C15	−175.14 (8)
O3—P1—O4—C13	28.84 (8)	C18—C13—C14—C19	−179.32 (9)
Li1—P1—O4—C13	175.22 (8)	O4—C13—C14—C19	5.24 (14)
P1—O3—C1—C2	−94.01 (10)	C13—C14—C15—C16	−0.31 (15)
P1—O3—C1—C6	91.40 (10)	C19—C14—C15—C16	179.32 (10)
O3—C1—C2—C3	−176.33 (8)	C14—C15—C16—C17	0.00 (17)
C6—C1—C2—C3	−2.06 (14)	C15—C16—C17—C18	0.36 (17)
O3—C1—C2—C7	3.54 (13)	C16—C17—C18—C13	−0.38 (15)
C6—C1—C2—C7	177.81 (9)	C16—C17—C18—C22	178.27 (10)
C1—C2—C3—C4	0.79 (14)	C14—C13—C18—C17	0.04 (15)
C7—C2—C3—C4	−179.08 (9)	O4—C13—C18—C17	175.49 (8)
C2—C3—C4—C5	0.71 (16)	C14—C13—C18—C22	−178.61 (9)
C3—C4—C5—C6	−1.07 (16)	O4—C13—C18—C22	−3.16 (13)
C4—C5—C6—C1	−0.11 (14)	C15—C14—C19—C20	62.20 (13)
C4—C5—C6—C10	175.93 (9)	C13—C14—C19—C20	−118.20 (11)
C2—C1—C6—C5	1.72 (14)	C15—C14—C19—C21	−60.88 (12)
O3—C1—C6—C5	176.02 (8)	C13—C14—C19—C21	118.73 (10)
C2—C1—C6—C10	−174.33 (9)	C17—C18—C22—C23	28.37 (14)
O3—C1—C6—C10	−0.04 (13)	C13—C18—C22—C23	−153.04 (10)
C1—C2—C7—C8	−127.00 (10)	C17—C18—C22—C24	−96.23 (12)
C3—C2—C7—C8	52.86 (13)	C13—C18—C22—C24	82.36 (12)
C1—C2—C7—C9	109.19 (11)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H26···O1	0.79 (2)	2.00 (2)	2.7482 (11)	158.2 (19)
O6—H28···O8^i	0.85 (2)	1.86 (2)	2.7013 (14)	174 (2)
O7—H30···O2^ii	0.83 (2)	1.89 (2)	2.7152 (11)	170.7 (19)
O8—H32···O1	0.82 (2)	1.88 (2)	2.6929 (12)	171.8 (19)

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