Tris(tetra­ethyl­ammonium) μ-3-hydroxy­propanolato-di-μ-methoxo-bis­[tricarbonyl­tungsten(0)]

In the crystal structure of the title compound, (C₈H₂₀N)₃[W₂(CH₃O)₂(C₃H₇O₂)(CO)₆], obtained from a ligand substitution reaction of (Et₄N)₃[W₂(OMe)₃(CO)₆], the trianion sits across a mirror plane such that one W(CO)₃ group is unique and the two meth­oxy groups and all but the middle C atom of the 3-hydroxy­propanolate ligand lie on the mirror plane. One and a half mol­ecules of the tetra­ethyl­ammonium cation are present to balance the charge in the asymmetric unit. The half mol­ecule is situated with its N atom on a mirror plane and is disordered.

Key indicators

• Single-crystal X-ray study
• T = 110 K
• Mean [sigma](C-C) = 0.005 Å
• H-atom completeness 98%
• Disorder in main residue
• R factor = 0.022
• wR factor = 0.060
• Data-to-parameter ratio = 18.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for         C8

Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       3.31
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.38 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       2.67 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C7
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C19
PLAT301_ALERT_3_C Main Residue  Disorder .........................       4.00 Perc.
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      33.00 Perc.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C8 H20 N
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C11 H11 O10 W2

Alert level G
FORMU01_ALERT_2_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and the formula from the _atom_site* data.
            Atom count from _chemical_formula_sum:C35 H73 N3 O10 W2
            Atom count from the _atom_site data:  C35 H71 N3 O10 W2
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional?
           From the CIF: _cell_formula_units_Z    4
           From the CIF: _chemical_formula_sum  C35 H73 N3 O10 W2
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C        140.00    140.00    0.00
           H        292.00    284.00    8.00
           N         12.00     12.00    0.00
           O         40.00     40.00    0.00
           W          8.00      8.00    0.00

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

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 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
   4 ALERT type 4 Improvement, methodology, query or suggestion

---

S1. Comment

Previously, we have presented the results of ligand exchange of the trianion of (Et₄N)₃[W₂(OMe)₃(CO)₆], (II), with aryl alcohols (Klausmeyer et al., 2003). Subsequently, we reported the complete exchange reaction with an alcohol containing an sp³ carbon (Klausmeyer & Adrian, 2004). In each of the previous examples, there was always complete exchange of all of the methoxy groups regardless of how much of the new alcohol was added. In the present study, we were able to isolate the first known singly substituted derivative, (Et₄N)₃[W₂(CO)₆(OCH₂CH₂CH₂OH)(CO)₆], (I).

The trianion sits across a mirror plane such that one W(CO)₃ group is unique and the two methoxy groups and all but the middle C atom (C7) of the 3-hydroxypropanolate ligand lie on the mirror plane. This forces the bridging ligands to be symmetric with respect to the W(CO)₃ groups.

The environment around the W atom is a distorted octahedral, comprised of three CO ligands and three O atoms from the bridging alkoxy ligands. The W—O bond lengths are all slightly different from each other. For W—O(methoxy), the bond lengths average 2.198 (3) Å, and for W—O(diol), the bond length is slightly shorter at 2.1844 (18) Å.

The W—O—W angles are nearly the same, averaging 96.2 (2)°. The bridging O atoms would all be expected to have near tetrahedral geometry, but only the methoxy ligands approach this geometry, with the sum of their angles being 338.8 (2)° for O4 and 343.7 (2)° for O5. The angles around O6 of the 3-hydroxypropanolate ligand sum to 359.98 (17)°, which means it is planar. The planarity of this O atom is likely due to the pendent OH group of the 3-hydroxypropanolate ligand which bends back around toward the metal centers in order to engage in hydrogen bonding with the bridging O atoms, viz. O6 and O5 (Table 2). This would account for the deviation in geometry from the expected values.

S2. Experimental

Complex (I) was obtained by the ligand-exchange reaction of (Et₄N)₃[W₂(OMe)₃(CO)₆] with 1 equivalent of 1,3-propanediol. In a typical experiment, (Et₄N)₃[W₂(OMe)₃(CO)₆] (0.100 g) was dissolved in CH₃CN (20 ml) and 1,3-propanediol (1 equivalent) in CH₃CN (15 ml) was added. This solution was allowed to stir for 1 h at room temperature. The solvent was then removed at reduced pressure to a final volume of about 5 ml and the complex was precipitated from solution by addition of ether (60 ml), resulting in an oily precipitate. Diffraction quality crystals of (I) were obtained by slow diffusion of ether into a concentrated acetonitrile solution.

S3. Refinement

One and a half tetraethylammonium cations are present to balance the charge in the asymmetric unit. The half molecule is situated with N2 on a mirror plane and is disordered. Occupancies of the C atoms of the disordered cation were constrained to sum to unity, and one half of the molecule was modeled while the other is symmetry generated. Refinement yielded an 0.51 (1)/0.49 (1) disorder of the C atoms. H atoms were included in calculated positions (C—H = 0.93 Å); isotropic displacement parameters were fixed [U_iso(H) = 1.2U_eq(C)]. The largest electron-density peak is 0.71 Å from atom W1.

Computing details

Data collection: APEX2 (Bruker, 2003); cell refinement: APEX2; data reduction: SAINT-Plus (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2000); software used to prepare material for publication: SHELXTL.

Figures

Fig. 1. A view of the molecular structure of (I). Displacement ellipsoids are drawn at the 50% probability level

Tris(tetraethylammonium) µ-3-hydroxypropanolato-di-µ-methoxo-bis[tricarbonyltungsten(0)]

Crystal data

(C8H20N)3[W2(CH3O)2(C3H7O2)(CO)6]	F(000) = 2120
Mr = 1063.63	Dx = 1.686 Mg m^−3
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 6700 reflections
a = 16.9476 (6) Å	θ = 2.5–34.5°
b = 24.1286 (9) Å	µ = 5.54 mm^−1
c = 10.2457 (4) Å	T = 110 K
V = 4189.7 (3) Å^3	Block, orange
Z = 4	0.26 × 0.15 × 0.13 mm

Data collection

Bruker SMART CCD area-detector diffractometer	5181 independent reflections
Radiation source: fine-focus sealed tube	4411 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
ϕ and ω scans	θmax = 28.3°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −22→22
Tmin = 0.297, Tmax = 0.485	k = −32→23
27335 measured reflections	l = −13→11

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)] = 0.022	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.060	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0293P)^2 + 7.8991P] where P = (Fo^2 + 2Fc^2)/3
5181 reflections	(Δ/σ)max = 0.004
274 parameters	Δρmax = 2.55 e Å^−3
5 restraints	Δρmin = −0.77 e Å^−3

Special details

Experimental. 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 > 2sigma(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.

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	Occ. (<1)
W1	0.120112 (6)	0.682331 (4)	1.400128 (11)	0.02087 (5)
O1	0.15179 (18)	0.59719 (10)	1.1764 (2)	0.0476 (6)
O2	−0.00686 (13)	0.59786 (9)	1.4974 (2)	0.0351 (5)
O3	0.24150 (14)	0.61157 (10)	1.5583 (2)	0.0353 (5)
O4	0.10259 (17)	0.7500	1.5404 (3)	0.0220 (6)
O5	0.19831 (17)	0.7500	1.3367 (3)	0.0241 (6)
N1	0.12964 (15)	0.50237 (11)	0.8078 (3)	0.0286 (5)
C1	0.13868 (19)	0.63054 (13)	1.2595 (3)	0.0312 (7)
C2	0.04105 (18)	0.63060 (12)	1.4595 (3)	0.0257 (6)
C3	0.19455 (17)	0.63833 (12)	1.4972 (3)	0.0261 (6)
C4	0.1402 (3)	0.7500	1.6612 (4)	0.0326 (10)
H4A	0.1254	0.7826	1.7090	0.049*	0.50
H4B	0.1963	0.7500	1.6485	0.049*
C5	0.2808 (3)	0.7500	1.3546 (5)	0.0305 (9)
H5A	0.3030	0.7835	1.3196	0.046*	0.50
H5B	0.2918	0.7500	1.4464	0.046*
O6	0.05275 (17)	0.7500	1.3127 (3)	0.0241 (6)
C6	−0.01112 (16)	0.7500	1.2256 (3)	0.0380 (11)
H6A	−0.0300	0.7884	1.2127	0.046*	0.50
H6B	−0.0550	0.7280	1.2627	0.046*	0.50
C7	0.01377 (16)	0.7250 (2)	1.0922 (3)	0.0393 (16)	0.50
H7A	0.0259	0.6853	1.1055	0.047*	0.50
H7B	−0.0320	0.7271	1.0324	0.047*	0.50
C8	0.07930 (16)	0.7500	1.0294 (3)	0.087 (3)
H8A	0.0794	0.7346	0.9398	0.104*	0.50
H8B	0.0650	0.7896	1.0201	0.104*	0.50
O7	0.15790 (16)	0.7500	1.0679 (3)	0.0588 (12)
H7	0.1605	0.7526	1.1496	0.088*	0.50
C9	0.21424 (19)	0.50277 (14)	0.7599 (4)	0.0361 (7)
H9A	0.2238	0.4682	0.7103	0.043*
H9B	0.2207	0.5341	0.6986	0.043*
C10	0.2768 (2)	0.50757 (17)	0.8650 (4)	0.0484 (9)
H10A	0.3292	0.5071	0.8246	0.073*
H10B	0.2720	0.4763	0.9256	0.073*
H10C	0.2696	0.5424	0.9128	0.073*
C11	0.07718 (19)	0.50265 (14)	0.6875 (3)	0.0336 (7)
H11A	0.0895	0.5362	0.6357	0.040*
H11B	0.0908	0.4700	0.6334	0.040*
C12	−0.0102 (2)	0.50168 (17)	0.7132 (4)	0.0445 (9)
H12A	−0.0388	0.5021	0.6301	0.067*
H12B	−0.0250	0.5343	0.7647	0.067*
H12C	−0.0239	0.4680	0.7617	0.067*
C13	0.1131 (2)	0.55184 (16)	0.8947 (3)	0.0381 (8)
H13A	0.1478	0.5497	0.9722	0.046*
H13B	0.0578	0.5496	0.9256	0.046*
C14	0.1253 (2)	0.60758 (16)	0.8293 (4)	0.0464 (9)
H14A	0.1125	0.6373	0.8910	0.070*
H14B	0.0908	0.6104	0.7528	0.070*
H14C	0.1805	0.6111	0.8018	0.070*
C15	0.1139 (2)	0.45127 (15)	0.8923 (3)	0.0344 (7)
H15A	0.1508	0.4517	0.9671	0.041*
H15B	0.0597	0.4538	0.9278	0.041*
C16	0.1224 (2)	0.39619 (15)	0.8209 (4)	0.0463 (9)
H16A	0.1097	0.3657	0.8806	0.069*
H16B	0.1768	0.3921	0.7898	0.069*
H16C	0.0862	0.3953	0.7463	0.069*
N2	−0.1305 (2)	0.7500	1.6477 (5)	0.0439 (11)	0.486 (6)
C17	−0.0956 (6)	0.7279 (4)	1.5275 (8)	0.060 (3)	0.486 (6)
H17A	−0.0456	0.7085	1.5474	0.072*	0.486 (6)
H17B	−0.0841	0.7585	1.4659	0.072*	0.486 (6)
C18	−0.1546 (7)	0.6877 (5)	1.4670 (10)	0.067 (3)	0.486 (6)
H18A	−0.1330	0.6730	1.3853	0.100*	0.486 (6)
H18B	−0.2041	0.7071	1.4490	0.100*	0.486 (6)
H18C	−0.1644	0.6571	1.5277	0.100*	0.486 (6)
C19	−0.1544 (4)	0.7116 (3)	1.7505 (7)	0.0343 (17)	0.486 (6)
H19A	−0.2031	0.6920	1.7234	0.041*	0.486 (6)
H19B	−0.1662	0.7326	1.8311	0.041*	0.486 (6)
C20	−0.0895 (19)	0.6690 (14)	1.778 (2)	0.061 (6)	0.486 (6)
H20A	−0.1073	0.6436	1.8470	0.091*	0.486 (6)
H20B	−0.0417	0.6883	1.8076	0.091*	0.486 (6)
H20C	−0.0779	0.6480	1.6989	0.091*	0.486 (6)
N2A	−0.1305 (2)	0.7500	1.6477 (5)	0.0439 (11)	0.514 (6)
C17A	−0.2027 (4)	0.7111 (3)	1.6167 (6)	0.0342 (16)	0.514 (6)
H17C	−0.2165	0.6912	1.6981	0.041*	0.514 (6)
H17D	−0.2481	0.7350	1.5944	0.041*	0.514 (6)
C18A	−0.1946 (6)	0.6680 (3)	1.5089 (8)	0.051 (2)	0.514 (6)
H18D	−0.2443	0.6475	1.5002	0.076*	0.514 (6)
H18E	−0.1520	0.6422	1.5309	0.076*	0.514 (6)
H18F	−0.1824	0.6866	1.4263	0.076*	0.514 (6)
C19A	−0.0633 (4)	0.7073 (3)	1.7043 (8)	0.049 (2)	0.514 (6)
H19C	−0.0474	0.6821	1.6327	0.058*	0.514 (6)
H19D	−0.0163	0.7292	1.7289	0.058*	0.514 (6)
C20A	−0.0868 (17)	0.6725 (12)	1.820 (2)	0.063 (6)	0.514 (6)
H20D	−0.0424	0.6489	1.8454	0.094*	0.514 (6)
H20E	−0.1320	0.6493	1.7960	0.094*	0.514 (6)
H20F	−0.1013	0.6968	1.8925	0.094*	0.514 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
W1	0.02378 (8)	0.01818 (7)	0.02066 (7)	0.00076 (4)	−0.00007 (4)	−0.00002 (4)
O1	0.0757 (19)	0.0329 (13)	0.0342 (13)	−0.0012 (13)	0.0128 (13)	−0.0093 (11)
O2	0.0331 (12)	0.0272 (12)	0.0451 (13)	−0.0044 (9)	0.0033 (10)	0.0035 (10)
O3	0.0351 (13)	0.0338 (12)	0.0368 (12)	0.0103 (10)	0.0031 (10)	0.0077 (10)
O4	0.0266 (15)	0.0201 (13)	0.0193 (13)	0.000	−0.0012 (11)	0.000
O5	0.0248 (15)	0.0227 (14)	0.0247 (14)	0.000	0.0001 (12)	0.000
N1	0.0286 (14)	0.0297 (14)	0.0276 (12)	0.0014 (10)	0.0033 (10)	0.0057 (11)
C1	0.0401 (18)	0.0261 (15)	0.0274 (14)	−0.0023 (13)	0.0068 (13)	0.0015 (12)
C2	0.0274 (15)	0.0230 (14)	0.0266 (14)	0.0049 (11)	−0.0026 (12)	0.0005 (11)
C3	0.0268 (15)	0.0243 (14)	0.0273 (13)	0.0027 (11)	0.0072 (12)	0.0009 (12)
C4	0.036 (2)	0.040 (3)	0.022 (2)	0.000	−0.0041 (18)	0.000
C5	0.022 (2)	0.035 (2)	0.035 (2)	0.000	0.0028 (18)	0.000
O6	0.0250 (15)	0.0237 (14)	0.0236 (14)	0.000	−0.0048 (12)	0.000
C6	0.031 (2)	0.048 (3)	0.035 (2)	0.000	−0.009 (2)	0.000
C7	0.048 (4)	0.042 (4)	0.028 (3)	−0.004 (3)	−0.004 (3)	0.001 (3)
C8	0.060 (5)	0.170 (9)	0.031 (3)	0.000	0.001 (3)	0.000
O7	0.050 (3)	0.092 (3)	0.0341 (19)	0.000	0.0103 (18)	0.000
C9	0.0311 (17)	0.0326 (17)	0.0447 (19)	0.0017 (13)	0.0043 (15)	0.0073 (15)
C10	0.035 (2)	0.043 (2)	0.067 (3)	−0.0010 (16)	−0.0100 (18)	0.0077 (19)
C11	0.0333 (18)	0.0348 (17)	0.0326 (16)	0.0044 (13)	−0.0026 (13)	0.0038 (14)
C12	0.0315 (18)	0.047 (2)	0.055 (2)	0.0012 (15)	−0.0003 (17)	0.0057 (19)
C13	0.046 (2)	0.0340 (18)	0.0343 (18)	0.0044 (14)	0.0075 (15)	−0.0007 (14)
C14	0.061 (3)	0.0295 (18)	0.049 (2)	0.0082 (16)	0.0085 (18)	0.0017 (16)
C15	0.0347 (18)	0.0316 (17)	0.0368 (18)	−0.0026 (13)	0.0019 (13)	0.0124 (14)
C16	0.054 (2)	0.0292 (18)	0.055 (2)	−0.0041 (15)	−0.0103 (18)	0.0094 (17)
N2	0.030 (2)	0.059 (3)	0.043 (2)	0.000	0.0118 (19)	0.000
C17	0.073 (6)	0.071 (6)	0.037 (4)	0.034 (5)	0.016 (4)	−0.002 (4)
C18	0.067 (7)	0.092 (9)	0.042 (5)	0.037 (6)	−0.012 (5)	−0.014 (5)
C19	0.030 (4)	0.042 (4)	0.030 (3)	0.002 (3)	0.003 (3)	0.004 (3)
C20	0.062 (9)	0.066 (9)	0.054 (11)	0.028 (7)	−0.012 (8)	0.012 (8)
N2A	0.030 (2)	0.059 (3)	0.043 (2)	0.000	0.0118 (19)	0.000
C17A	0.030 (4)	0.038 (4)	0.034 (3)	−0.009 (3)	0.004 (3)	−0.001 (3)
C18A	0.061 (6)	0.041 (4)	0.050 (5)	−0.014 (4)	0.026 (4)	−0.016 (4)
C19A	0.035 (4)	0.055 (5)	0.056 (5)	−0.004 (3)	0.004 (4)	−0.015 (4)
C20A	0.051 (8)	0.058 (8)	0.080 (16)	0.008 (6)	0.003 (10)	0.021 (10)

Geometric parameters (Å, º)

W1—C3	1.926 (3)	C12—H12B	0.9800
W1—C2	1.930 (3)	C12—H12C	0.9800
W1—C1	1.933 (3)	C13—C14	1.517 (5)
W1—O6	2.1844 (18)	C13—H13A	0.9900
W1—O4	2.1952 (19)	C13—H13B	0.9900
W1—O5	2.2010 (19)	C14—H14A	0.9800
O1—C1	1.193 (4)	C14—H14B	0.9800
O2—C2	1.198 (4)	C14—H14C	0.9800
O3—C3	1.201 (4)	C15—C16	1.524 (5)
O4—C4	1.392 (5)	C15—H15A	0.9900
O4—W1^i	2.1952 (19)	C15—H15B	0.9900
O5—C5	1.411 (5)	C16—H16A	0.9800
O5—W1^i	2.2010 (19)	C16—H16B	0.9800
N1—C13	1.515 (4)	C16—H16C	0.9800
N1—C9	1.516 (4)	N2—C19^i	1.460 (7)
N1—C11	1.520 (4)	N2—C19	1.460 (7)
N1—C15	1.530 (4)	N2—C17	1.467 (8)
C4—H4A	0.9599	N2—C17^i	1.467 (8)
C4—H4B	0.9600	C17—C18	1.525 (12)
C5—H5A	0.9600	C17—H17A	0.9900
C5—H5B	0.9587	C17—H17B	0.9900
O6—C6	1.403 (4)	C18—H18A	0.9800
O6—W1^i	2.1844 (18)	C18—H18B	0.9800
C6—C7	1.5522	C18—H18C	0.9800
C6—H6A	0.9900	C19—C20	1.53 (3)
C6—H6B	0.9900	C19—H19A	0.9900
C7—C8	1.4181	C19—H19B	0.9900
C7—H7A	0.9900	C20—H20A	0.9800
C7—H7B	0.9900	C20—H20B	0.9800
C8—O7	1.389 (4)	C20—H20C	0.9800
C8—H8A	0.9900	C17A—C18A	1.522 (9)
C8—H8B	0.9900	C17A—H17C	0.9900
O7—H7	0.8400	C17A—H17D	0.9900
C9—C10	1.515 (5)	C18A—H18D	0.9800
C9—H9A	0.9900	C18A—H18E	0.9800
C9—H9B	0.9900	C18A—H18F	0.9800
C10—H10A	0.9800	C19A—C20A	1.50 (3)
C10—H10B	0.9800	C19A—H19C	0.9900
C10—H10C	0.9800	C19A—H19D	0.9900
C11—C12	1.505 (5)	C20A—H20D	0.9800
C11—H11A	0.9900	C20A—H20E	0.9800
C11—H11B	0.9900	C20A—H20F	0.9800
C12—H12A	0.9800
C3—W1—C2	86.30 (12)	C11—C12—H12B	109.5
C3—W1—C1	85.52 (13)	H12A—C12—H12B	109.5
C2—W1—C1	85.97 (13)	C11—C12—H12C	109.5
C3—W1—O6	165.09 (11)	H12A—C12—H12C	109.5
C2—W1—O6	104.47 (11)	H12B—C12—H12C	109.5
C1—W1—O6	105.23 (12)	N1—C13—C14	114.4 (3)
C3—W1—O4	99.24 (11)	N1—C13—H13A	108.7
C2—W1—O4	100.42 (11)	C14—C13—H13A	108.7
C1—W1—O4	172.22 (11)	N1—C13—H13B	108.7
O6—W1—O4	69.01 (9)	C14—C13—H13B	108.7
C3—W1—O5	99.61 (11)	H13A—C13—H13B	107.6
C2—W1—O5	172.32 (10)	C13—C14—H14A	109.5
C1—W1—O5	99.30 (11)	C13—C14—H14B	109.5
O6—W1—O5	68.84 (10)	H14A—C14—H14B	109.5
O4—W1—O5	73.92 (9)	C13—C14—H14C	109.5
C4—O4—W1^i	121.34 (15)	H14A—C14—H14C	109.5
C4—O4—W1	121.34 (15)	H14B—C14—H14C	109.5
W1^i—O4—W1	96.11 (11)	C16—C15—N1	114.5 (3)
C5—O5—W1	123.97 (13)	C16—C15—H15A	108.6
C5—O5—W1^i	123.97 (13)	N1—C15—H15A	108.6
W1—O5—W1^i	95.77 (11)	C16—C15—H15B	108.6
C13—N1—C9	111.1 (3)	N1—C15—H15B	108.6
C13—N1—C11	111.4 (2)	H15A—C15—H15B	107.6
C9—N1—C11	106.9 (2)	C15—C16—H16A	109.5
C13—N1—C15	105.7 (3)	C15—C16—H16B	109.5
C9—N1—C15	110.7 (2)	H16A—C16—H16B	109.5
C11—N1—C15	111.1 (2)	C15—C16—H16C	109.5
O1—C1—W1	177.3 (3)	H16A—C16—H16C	109.5
O2—C2—W1	178.7 (3)	H16B—C16—H16C	109.5
O3—C3—W1	179.1 (3)	C19^i—N2—C19	78.9 (6)
O4—C4—H4A	109.5	C19^i—N2—C17	161.5 (5)
O4—C4—H4B	109.4	C19—N2—C17	119.1 (5)
H4A—C4—H4B	109.2	C19^i—N2—C17^i	119.1 (5)
O5—C5—H5A	109.9	C19—N2—C17^i	161.5 (5)
O5—C5—H5B	108.6	N2—C17—C18	108.0 (7)
H5A—C5—H5B	106.9	N2—C17—H17A	110.1
C6—O6—W1^i	131.62 (5)	C18—C17—H17A	110.1
C6—O6—W1	131.62 (5)	N2—C17—H17B	110.1
W1^i—O6—W1	96.74 (11)	C18—C17—H17B	110.1
O6—C6—C7	110.52 (15)	H17A—C17—H17B	108.4
O6—C6—H6A	109.5	C17—C18—H18A	109.5
C7—C6—H6A	109.5	C17—C18—H18B	109.5
O6—C6—H6B	109.5	H18A—C18—H18B	109.5
C7—C6—H6B	109.5	C17—C18—H18C	109.5
H6A—C6—H6B	108.1	H18A—C18—H18C	109.5
C8—C7—C6	116.6	H18B—C18—H18C	109.5
C8—C7—H7A	108.2	N2—C19—C20	111.2 (13)
C6—C7—H7A	108.2	N2—C19—H19A	109.4
C8—C7—H7B	108.2	C20—C19—H19A	109.4
C6—C7—H7B	108.2	N2—C19—H19B	109.4
H7A—C7—H7B	107.3	C20—C19—H19B	109.4
O7—C8—C7	128.5	H19A—C19—H19B	108.0
O7—C8—H8A	105.2	C19—C20—H20A	109.5
C7—C8—H8A	105.2	C19—C20—H20B	109.5
O7—C8—H8B	105.2	H20A—C20—H20B	109.5
C7—C8—H8B	105.2	C19—C20—H20C	109.5
H8A—C8—H8B	105.9	H20A—C20—H20C	109.5
C8—O7—H7	109.5	H20B—C20—H20C	109.5
C10—C9—N1	115.6 (3)	C18A—C17A—H17C	107.6
C10—C9—H9A	108.4	C18A—C17A—H17D	107.6
N1—C9—H9A	108.4	H17C—C17A—H17D	107.0
C10—C9—H9B	108.4	C17A—C18A—H18D	109.5
N1—C9—H9B	108.4	C17A—C18A—H18E	109.5
H9A—C9—H9B	107.4	H18D—C18A—H18E	109.5
C9—C10—H10A	109.5	C17A—C18A—H18F	109.5
C9—C10—H10B	109.5	H18D—C18A—H18F	109.5
H10A—C10—H10B	109.5	H18E—C18A—H18F	109.5
C9—C10—H10C	109.5	C20A—C19A—H19C	108.2
H10A—C10—H10C	109.5	C20A—C19A—H19D	108.2
H10B—C10—H10C	109.5	H19C—C19A—H19D	107.3
C12—C11—N1	115.7 (3)	C19A—C20A—H20D	109.5
C12—C11—H11A	108.4	C19A—C20A—H20E	109.5
N1—C11—H11A	108.4	H20D—C20A—H20E	109.5
C12—C11—H11B	108.4	C19A—C20A—H20F	109.5
N1—C11—H11B	108.4	H20D—C20A—H20F	109.5
H11A—C11—H11B	107.4	H20E—C20A—H20F	109.5
C11—C12—H12A	109.5

Symmetry code: (i) x, −y+3/2, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7···O5	0.84	2.02	2.838 (4)	163
O7—H7···O6	0.84	2.48	3.077 (4)	129