Tris­(tetraethyl­ammonium) tris(μ-4-pyridine­methano­lato)­bis­[tri­carbonyl­tungsten(0)] aceto­nitrile trisolvate

The title compound, (C₈H₂₀N)₃[W₂(C₆H₆NO)₃(CO)₆]·3C₂H₃N, was obtained from a ligand-substitution reaction of [Et₄N]₃[W₂(CO)₆(OMe)₃]. The structure is an example of a triply bridged ditungsten(0) unit that contains an alkyl as well as an aryl portion. The aryl rings are seen to adopt a conformation considerably skew to the W...W axis, as opposed to the aryl alcohol derivatives previously characterized.

Key indicators

• Single-crystal X-ray study
• T = 110 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.018
• wR factor = 0.042
• Data-to-parameter ratio = 26.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT223_ALERT_4_C Large Solvent/Anion  H     Ueq(max)/Ueq(min) ...       3.33 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O1     -   C1      ..       5.97 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O2     -   C2      ..       6.92 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O3     -   C3      ..       6.67 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O5     -   C5      ..       5.57 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O6     -   C6      ..       5.06 su
PLAT411_ALERT_2_C Short Inter H...H Contact  H41B   ..  H41B    ..       2.14 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H27B   ..  N1      ..       2.69 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H25A   ..  N3      ..       2.64 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  10 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
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion

---

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 (Bruker, 2000); software used to prepare material for publication: SHELXTL.

Tris(tetraethylammonium) tris(µ-4-pyridinemethanolato)bis[tricarbonyltungsten(0)] acetonitrile trisolvate

Crystal data

(C8H20N)3[W2(C6H6NO)3(CO)6]·3C2H3N	Z = 2
Mr = 1374.03	F(000) = 1388
Triclinic, P1	Dx = 1.538 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 12.6005 (2) Å	Cell parameters from 7145 reflections
b = 14.0970 (2) Å	θ = 2.6–30.5°
c = 18.3091 (3) Å	µ = 3.93 mm^−1
α = 83.206 (1)°	T = 110 K
β = 75.675 (1)°	Prism, orange
γ = 70.433 (1)°	0.19 × 0.13 × 0.11 mm
V = 2966.90 (8) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	17950 independent reflections
Radiation source: fine-focus sealed tube	15425 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
φ and ω scans	θmax = 30.6°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→18
Tmin = 0.506, Tmax = 0.646	k = −20→12
41376 measured reflections	l = −25→26

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)] = 0.018	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.042	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0198P)^2] where P = (Fo^2 + 2Fc^2)/3
17950 reflections	(Δ/σ)max = 0.007
682 parameters	Δρmax = 1.01 e Å^−3
5 restraints	Δρmin = −0.56 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
C1	0.40972 (14)	0.24109 (13)	0.27844 (9)	0.0158 (3)
C2	0.50046 (14)	0.14748 (12)	0.15657 (9)	0.0157 (3)
C3	0.47723 (14)	0.05083 (12)	0.29329 (9)	0.0154 (3)
C4	0.92178 (14)	0.04873 (12)	0.30868 (9)	0.0147 (3)
C5	0.93909 (14)	0.14183 (12)	0.17047 (9)	0.0147 (3)
C6	0.86197 (13)	0.24105 (12)	0.29114 (9)	0.0148 (3)
C7	0.78833 (14)	0.00404 (12)	0.14212 (9)	0.0162 (3)
H7A	0.8108	0.0576	0.1083	0.019*
H7B	0.7286	−0.0111	0.1235	0.019*
C8	0.89271 (14)	−0.08946 (13)	0.13767 (10)	0.0173 (3)
C9	0.93339 (15)	−0.13652 (13)	0.20104 (11)	0.0208 (4)
H9	0.8995	−0.1076	0.2490	0.025*
C10	1.02470 (16)	−0.22684 (14)	0.19311 (12)	0.0283 (4)
H10	1.0506	−0.2584	0.2371	0.034*
C11	1.03982 (17)	−0.22424 (16)	0.06715 (12)	0.0332 (5)
H11	1.0770	−0.2536	0.0196	0.040*
C12	0.94934 (16)	−0.13474 (14)	0.06900 (11)	0.0252 (4)
H12	0.9262	−0.1046	0.0238	0.030*
C13	0.62499 (14)	0.11740 (13)	0.40658 (9)	0.0156 (3)
H13A	0.6920	0.0607	0.4170	0.019*
H13B	0.5577	0.0927	0.4167	0.019*
C14	0.59949 (13)	0.20126 (12)	0.45947 (9)	0.0139 (3)
C15	0.56624 (14)	0.18650 (13)	0.53756 (9)	0.0169 (3)
H15	0.5590	0.1235	0.5587	0.020*
C16	0.54400 (14)	0.26526 (14)	0.58355 (9)	0.0201 (3)
H16	0.5209	0.2540	0.6364	0.024*
C17	0.58515 (15)	0.36885 (13)	0.48390 (10)	0.0204 (3)
H17	0.5927	0.4324	0.4646	0.024*
C18	0.60840 (14)	0.29539 (12)	0.43269 (9)	0.0163 (3)
H18	0.6301	0.3093	0.3801	0.020*
C19	0.67902 (14)	0.29002 (12)	0.13525 (9)	0.0162 (3)
H19A	0.6479	0.2613	0.1017	0.019*
H19B	0.7616	0.2801	0.1120	0.019*
C20	0.61533 (13)	0.40125 (12)	0.14063 (9)	0.0150 (3)
C21	0.55707 (16)	0.44479 (13)	0.20924 (10)	0.0224 (4)
H21	0.5560	0.4049	0.2549	0.027*
C22	0.50001 (18)	0.54830 (15)	0.21013 (12)	0.0302 (4)
H22	0.4602	0.5770	0.2576	0.036*
C23	0.55355 (16)	0.56628 (14)	0.08312 (12)	0.0283 (4)
H23	0.5530	0.6081	0.0384	0.034*
C24	0.61218 (15)	0.46470 (14)	0.07594 (10)	0.0220 (4)
H24	0.6500	0.4381	0.0275	0.026*
C25	0.35001 (16)	0.84101 (13)	0.23054 (10)	0.0191 (3)
H25A	0.4218	0.7848	0.2139	0.023*
H25B	0.3669	0.8829	0.2631	0.023*
C26	0.25902 (17)	0.79749 (15)	0.27735 (11)	0.0272 (4)
H26A	0.1869	0.8522	0.2936	0.041*
H26B	0.2855	0.7605	0.3217	0.041*
H26C	0.2457	0.7515	0.2470	0.041*
C27	0.30221 (16)	0.83809 (13)	0.10817 (10)	0.0215 (4)
H27A	0.3733	0.7795	0.0969	0.026*
H27B	0.2383	0.8120	0.1344	0.026*
C28	0.27605 (18)	0.88983 (16)	0.03426 (11)	0.0291 (4)
H28A	0.2037	0.9460	0.0444	0.044*
H28B	0.2684	0.8415	0.0032	0.044*
H28C	0.3391	0.9154	0.0074	0.044*
C29	0.41404 (15)	0.94922 (13)	0.12527 (10)	0.0201 (3)
H29A	0.4298	0.9814	0.1649	0.024*
H29B	0.3861	1.0028	0.0880	0.024*
C30	0.52698 (16)	0.87488 (16)	0.08602 (11)	0.0292 (4)
H30A	0.5503	0.8165	0.1201	0.044*
H30B	0.5870	0.9076	0.0724	0.044*
H30C	0.5164	0.8527	0.0403	0.044*
C31	0.20616 (14)	0.99073 (13)	0.18189 (10)	0.0193 (3)
H31A	0.1895	1.0299	0.1352	0.023*
H31B	0.1428	0.9620	0.2033	0.023*
C32	0.20592 (16)	1.06199 (13)	0.23774 (10)	0.0224 (4)
H32A	0.2239	1.0240	0.2839	0.034*
H32B	0.1295	1.1129	0.2498	0.034*
H32C	0.2642	1.0952	0.2156	0.034*
C33	−0.02647 (13)	0.20792 (13)	0.53084 (9)	0.0169 (3)
H33A	−0.0204	0.1428	0.5593	0.020*
H33B	−0.0419	0.2596	0.5677	0.020*
C34	−0.12870 (15)	0.23488 (14)	0.49397 (11)	0.0235 (4)
H34A	−0.1413	0.3027	0.4704	0.035*
H34B	−0.1979	0.2331	0.5323	0.035*
H34C	−0.1129	0.1863	0.4554	0.035*
C35	0.12568 (15)	0.11262 (13)	0.42475 (9)	0.0184 (3)
H35A	0.0630	0.1216	0.3983	0.022*
H35B	0.1947	0.1165	0.3860	0.022*
C36	0.15328 (16)	0.00887 (13)	0.46182 (11)	0.0241 (4)
H36A	0.2269	−0.0080	0.4772	0.036*
H36B	0.1592	−0.0402	0.4261	0.036*
H36C	0.0918	0.0072	0.5063	0.036*
C37	0.08217 (15)	0.29325 (13)	0.42537 (10)	0.0202 (3)
H37A	0.1593	0.2854	0.3921	0.024*
H37B	0.0282	0.2982	0.3928	0.024*
C38	0.04279 (18)	0.39050 (14)	0.46621 (12)	0.0281 (4)
H38A	−0.0350	0.4007	0.4977	0.042*
H38B	0.0417	0.4469	0.4293	0.042*
H38C	0.0961	0.3869	0.4981	0.042*
C39	0.17516 (14)	0.18393 (14)	0.52599 (10)	0.0197 (3)
H39A	0.1741	0.1238	0.5598	0.024*
H39B	0.1494	0.2427	0.5581	0.024*
C40	0.29871 (15)	0.17007 (16)	0.48300 (11)	0.0281 (4)
H40A	0.3256	0.1117	0.4511	0.042*
H40B	0.3484	0.1590	0.5188	0.042*
H40C	0.3018	0.2306	0.4513	0.042*
C41	0.01682 (15)	0.46120 (15)	0.09930 (10)	0.0223 (4)
H41A	−0.0154	0.5321	0.1145	0.027*
H41B	0.0434	0.4619	0.0437	0.027*
C42	−0.07915 (16)	0.41446 (16)	0.12078 (12)	0.0280 (4)
H42A	−0.0504	0.3459	0.1024	0.042*
H42B	−0.1436	0.4550	0.0980	0.042*
H42C	−0.1057	0.4122	0.1758	0.042*
C43	0.20569 (15)	0.46710 (14)	0.10233 (10)	0.0200 (3)
H43A	0.2273	0.4629	0.0467	0.024*
H43B	0.1661	0.5389	0.1140	0.024*
C44	0.31528 (16)	0.43120 (16)	0.13195 (12)	0.0295 (4)
H44A	0.2954	0.4358	0.1869	0.044*
H44B	0.3638	0.4735	0.1095	0.044*
H44C	0.3575	0.3611	0.1186	0.044*
C45	0.08554 (16)	0.41106 (16)	0.21902 (10)	0.0274 (4)
H45A	0.0312	0.3720	0.2371	0.033*
H45B	0.1551	0.3768	0.2396	0.033*
C46	0.0294 (2)	0.5154 (2)	0.25001 (12)	0.0440 (6)
H46A	0.0834	0.5542	0.2338	0.066*
H46B	0.0093	0.5101	0.3052	0.066*
H46C	−0.0407	0.5496	0.2310	0.066*
C47	0.17266 (17)	0.29930 (14)	0.11418 (13)	0.0320 (5)
H47A	0.2414	0.2692	0.1363	0.038*
H47B	0.1158	0.2644	0.1386	0.038*
C48	0.2081 (2)	0.2790 (2)	0.03131 (16)	0.0533 (7)
H48A	0.1402	0.3056	0.0090	0.080*
H48B	0.2415	0.2062	0.0246	0.080*
H48C	0.2656	0.3120	0.0064	0.080*
C49	0.25601 (17)	0.42649 (16)	0.63046 (11)	0.0288 (4)
C50	0.29743 (18)	0.47579 (15)	0.67797 (11)	0.0287 (4)
H50A	0.3806	0.4634	0.6593	0.043*
H50B	0.2825	0.4487	0.7300	0.043*
H50C	0.2570	0.5485	0.6767	0.043*
C51	0.24848 (18)	0.53415 (16)	0.37285 (11)	0.0289 (4)
C52	0.34246 (19)	0.46090 (16)	0.40172 (12)	0.0339 (5)
H52A	0.4011	0.4919	0.4025	0.051*
H52B	0.3772	0.4030	0.3691	0.051*
H52C	0.3126	0.4383	0.4530	0.051*
C53	0.7351 (2)	0.74768 (18)	0.21040 (16)	0.0419 (6)
C54	0.6767 (2)	0.82389 (19)	0.26589 (17)	0.0580 (8)
H54A	0.5931	0.8377	0.2747	0.087*
H54B	0.6955	0.8858	0.2474	0.087*
H54C	0.7019	0.7999	0.3132	0.087*
N1	1.07830 (14)	−0.27200 (13)	0.12758 (11)	0.0342 (4)
N2	0.55268 (13)	0.35592 (12)	0.55891 (8)	0.0219 (3)
N3	0.49748 (15)	0.60980 (12)	0.14878 (10)	0.0312 (4)
N4	0.31836 (12)	0.90465 (10)	0.16125 (8)	0.0155 (3)
N5	0.08908 (11)	0.19957 (11)	0.47682 (8)	0.0152 (3)
N6	0.12056 (12)	0.40940 (11)	0.13345 (8)	0.0170 (3)
N7	0.22483 (17)	0.38676 (17)	0.59351 (12)	0.0461 (5)
N8	0.17488 (17)	0.59296 (15)	0.35070 (11)	0.0398 (4)
N9	0.7812 (2)	0.68626 (17)	0.16752 (15)	0.0538 (6)
O1	0.31481 (10)	0.29822 (10)	0.29794 (7)	0.0238 (3)
O2	0.46010 (11)	0.15579 (10)	0.10291 (7)	0.0234 (3)
O3	0.42292 (11)	−0.00289 (9)	0.32576 (7)	0.0213 (3)
O4	0.98929 (11)	−0.00803 (10)	0.34233 (7)	0.0222 (3)
O5	1.01395 (10)	0.14616 (9)	0.11705 (7)	0.0208 (3)
O6	0.89876 (11)	0.29934 (10)	0.31143 (7)	0.0224 (3)
O7	0.74032 (9)	0.04028 (8)	0.21508 (6)	0.0133 (2)
O8	0.64883 (9)	0.14822 (9)	0.33081 (6)	0.0134 (2)
O9	0.67050 (9)	0.23783 (8)	0.20478 (6)	0.0138 (2)
W1	0.558679 (5)	0.143507 (4)	0.245447 (3)	0.01109 (2)
W2	0.813217 (5)	0.143043 (4)	0.255652 (3)	0.01097 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0180 (8)	0.0175 (8)	0.0138 (7)	−0.0086 (6)	−0.0045 (6)	0.0030 (6)
C2	0.0140 (7)	0.0142 (8)	0.0181 (8)	−0.0055 (6)	−0.0012 (6)	0.0004 (6)
C3	0.0146 (7)	0.0164 (8)	0.0147 (7)	−0.0025 (6)	−0.0054 (6)	−0.0010 (6)
C4	0.0152 (7)	0.0164 (8)	0.0131 (7)	−0.0072 (6)	−0.0009 (6)	−0.0009 (6)
C5	0.0139 (7)	0.0137 (8)	0.0165 (8)	−0.0019 (6)	−0.0067 (6)	−0.0004 (6)
C6	0.0127 (7)	0.0166 (8)	0.0139 (7)	−0.0050 (6)	−0.0021 (6)	0.0028 (6)
C7	0.0179 (8)	0.0155 (8)	0.0148 (7)	−0.0032 (6)	−0.0049 (6)	−0.0024 (6)
C8	0.0163 (8)	0.0149 (8)	0.0213 (8)	−0.0061 (6)	−0.0021 (6)	−0.0042 (6)
C9	0.0193 (8)	0.0171 (8)	0.0274 (9)	−0.0040 (7)	−0.0085 (7)	−0.0047 (7)
C10	0.0233 (9)	0.0211 (10)	0.0419 (12)	−0.0022 (7)	−0.0152 (8)	−0.0048 (8)
C11	0.0275 (10)	0.0296 (11)	0.0370 (12)	−0.0047 (8)	0.0042 (9)	−0.0176 (9)
C12	0.0254 (9)	0.0234 (10)	0.0233 (9)	−0.0053 (8)	0.0007 (7)	−0.0074 (8)
C13	0.0188 (8)	0.0171 (8)	0.0117 (7)	−0.0074 (6)	−0.0036 (6)	0.0013 (6)
C14	0.0094 (7)	0.0173 (8)	0.0135 (7)	−0.0022 (6)	−0.0032 (5)	0.0000 (6)
C15	0.0156 (8)	0.0191 (8)	0.0152 (8)	−0.0056 (6)	−0.0033 (6)	0.0023 (6)
C16	0.0181 (8)	0.0286 (10)	0.0132 (8)	−0.0079 (7)	−0.0013 (6)	−0.0021 (7)
C17	0.0205 (8)	0.0178 (9)	0.0218 (9)	−0.0064 (7)	−0.0019 (7)	−0.0022 (7)
C18	0.0161 (8)	0.0168 (8)	0.0136 (7)	−0.0040 (6)	−0.0016 (6)	0.0006 (6)
C19	0.0162 (8)	0.0137 (8)	0.0159 (8)	−0.0025 (6)	−0.0025 (6)	0.0013 (6)
C20	0.0132 (7)	0.0131 (8)	0.0199 (8)	−0.0057 (6)	−0.0050 (6)	0.0016 (6)
C21	0.0270 (9)	0.0168 (9)	0.0211 (9)	−0.0035 (7)	−0.0067 (7)	0.0001 (7)
C22	0.0349 (11)	0.0210 (10)	0.0297 (10)	−0.0020 (8)	−0.0062 (8)	−0.0046 (8)
C23	0.0260 (10)	0.0192 (9)	0.0349 (11)	−0.0056 (8)	−0.0069 (8)	0.0126 (8)
C24	0.0195 (8)	0.0201 (9)	0.0234 (9)	−0.0063 (7)	−0.0027 (7)	0.0057 (7)
C25	0.0229 (8)	0.0178 (8)	0.0173 (8)	−0.0044 (7)	−0.0093 (7)	0.0012 (6)
C26	0.0321 (10)	0.0279 (10)	0.0233 (9)	−0.0130 (8)	−0.0086 (8)	0.0084 (8)
C27	0.0268 (9)	0.0191 (9)	0.0204 (9)	−0.0053 (7)	−0.0095 (7)	−0.0047 (7)
C28	0.0330 (11)	0.0338 (11)	0.0197 (9)	−0.0042 (9)	−0.0115 (8)	−0.0050 (8)
C29	0.0196 (8)	0.0193 (9)	0.0213 (8)	−0.0074 (7)	−0.0029 (7)	0.0004 (7)
C30	0.0188 (9)	0.0395 (12)	0.0244 (10)	−0.0044 (8)	−0.0008 (7)	−0.0052 (9)
C31	0.0160 (8)	0.0183 (9)	0.0204 (8)	−0.0004 (6)	−0.0047 (6)	−0.0023 (7)
C32	0.0223 (9)	0.0194 (9)	0.0225 (9)	−0.0012 (7)	−0.0050 (7)	−0.0055 (7)
C33	0.0129 (7)	0.0192 (8)	0.0160 (8)	−0.0044 (6)	−0.0003 (6)	0.0009 (6)
C34	0.0155 (8)	0.0262 (10)	0.0269 (9)	−0.0072 (7)	−0.0036 (7)	0.0053 (8)
C35	0.0177 (8)	0.0228 (9)	0.0153 (8)	−0.0060 (7)	−0.0034 (6)	−0.0051 (7)
C36	0.0246 (9)	0.0196 (9)	0.0277 (10)	−0.0021 (7)	−0.0093 (7)	−0.0062 (7)
C37	0.0199 (8)	0.0219 (9)	0.0190 (8)	−0.0095 (7)	−0.0034 (7)	0.0046 (7)
C38	0.0326 (11)	0.0202 (9)	0.0323 (10)	−0.0108 (8)	−0.0073 (8)	0.0037 (8)
C39	0.0174 (8)	0.0244 (9)	0.0184 (8)	−0.0052 (7)	−0.0056 (6)	−0.0060 (7)
C40	0.0176 (9)	0.0403 (12)	0.0305 (10)	−0.0113 (8)	−0.0064 (7)	−0.0080 (9)
C41	0.0182 (8)	0.0291 (10)	0.0203 (9)	−0.0069 (7)	−0.0090 (7)	0.0052 (7)
C42	0.0183 (9)	0.0351 (11)	0.0330 (11)	−0.0096 (8)	−0.0100 (8)	0.0017 (9)
C43	0.0178 (8)	0.0214 (9)	0.0215 (8)	−0.0097 (7)	−0.0044 (7)	0.0065 (7)
C44	0.0217 (9)	0.0355 (12)	0.0353 (11)	−0.0162 (8)	−0.0100 (8)	0.0119 (9)
C45	0.0226 (9)	0.0446 (12)	0.0194 (9)	−0.0180 (9)	−0.0089 (7)	0.0131 (8)
C46	0.0414 (13)	0.0669 (18)	0.0250 (11)	−0.0203 (12)	0.0000 (9)	−0.0129 (11)
C47	0.0192 (9)	0.0169 (9)	0.0583 (14)	−0.0041 (7)	−0.0079 (9)	−0.0021 (9)
C48	0.0356 (13)	0.0497 (16)	0.0728 (19)	−0.0150 (12)	0.0091 (12)	−0.0358 (14)
C49	0.0240 (9)	0.0316 (11)	0.0259 (10)	−0.0065 (8)	−0.0003 (8)	−0.0009 (8)
C50	0.0323 (11)	0.0265 (10)	0.0252 (10)	−0.0106 (8)	0.0001 (8)	−0.0029 (8)
C51	0.0313 (11)	0.0304 (11)	0.0289 (10)	−0.0180 (9)	−0.0011 (8)	−0.0035 (8)
C52	0.0383 (12)	0.0345 (12)	0.0344 (11)	−0.0167 (10)	−0.0103 (9)	−0.0023 (9)
C53	0.0290 (11)	0.0275 (12)	0.0682 (17)	−0.0109 (10)	−0.0172 (11)	0.0220 (12)
C54	0.0335 (13)	0.0308 (13)	0.087 (2)	−0.0061 (10)	0.0129 (13)	0.0153 (13)
N1	0.0226 (8)	0.0233 (9)	0.0526 (12)	0.0010 (7)	−0.0070 (8)	−0.0139 (8)
N2	0.0178 (7)	0.0257 (8)	0.0204 (7)	−0.0058 (6)	0.0008 (6)	−0.0079 (6)
N3	0.0310 (9)	0.0147 (8)	0.0429 (10)	−0.0021 (7)	−0.0080 (8)	0.0021 (7)
N4	0.0167 (7)	0.0143 (7)	0.0147 (6)	−0.0021 (5)	−0.0052 (5)	−0.0019 (5)
N5	0.0138 (6)	0.0171 (7)	0.0145 (6)	−0.0047 (5)	−0.0033 (5)	−0.0007 (5)
N6	0.0142 (7)	0.0167 (7)	0.0202 (7)	−0.0056 (5)	−0.0054 (5)	0.0042 (6)
N7	0.0420 (12)	0.0590 (14)	0.0418 (11)	−0.0192 (10)	−0.0093 (9)	−0.0107 (10)
N8	0.0393 (11)	0.0349 (11)	0.0463 (12)	−0.0136 (9)	−0.0079 (9)	−0.0035 (9)
N9	0.0544 (14)	0.0393 (13)	0.0742 (17)	−0.0181 (11)	−0.0280 (13)	0.0116 (12)
O1	0.0150 (6)	0.0271 (7)	0.0222 (6)	−0.0002 (5)	−0.0015 (5)	0.0017 (5)
O2	0.0255 (7)	0.0314 (7)	0.0178 (6)	−0.0119 (6)	−0.0101 (5)	0.0016 (5)
O3	0.0237 (6)	0.0227 (7)	0.0216 (6)	−0.0142 (5)	−0.0054 (5)	0.0042 (5)
O4	0.0200 (6)	0.0246 (7)	0.0207 (6)	−0.0051 (5)	−0.0083 (5)	0.0061 (5)
O5	0.0158 (6)	0.0258 (7)	0.0166 (6)	−0.0046 (5)	0.0003 (5)	0.0008 (5)
O6	0.0257 (7)	0.0244 (7)	0.0230 (6)	−0.0152 (5)	−0.0054 (5)	−0.0024 (5)
O7	0.0131 (5)	0.0132 (5)	0.0130 (5)	−0.0028 (4)	−0.0030 (4)	−0.0022 (4)
O8	0.0126 (5)	0.0190 (6)	0.0098 (5)	−0.0072 (4)	−0.0020 (4)	0.0002 (4)
O9	0.0121 (5)	0.0123 (5)	0.0163 (5)	−0.0043 (4)	−0.0033 (4)	0.0040 (4)
W1	0.01042 (3)	0.01134 (3)	0.01164 (3)	−0.00354 (2)	−0.00291 (2)	0.00027 (2)
W2	0.01011 (3)	0.01131 (3)	0.01143 (3)	−0.00337 (2)	−0.00230 (2)	−0.00049 (2)

Geometric parameters (Å, º)

C1—O1	1.191 (2)	C32—H32B	0.9800
C1—W1	1.9200 (17)	C32—H32C	0.9800
C2—O2	1.1907 (19)	C33—C34	1.517 (2)
C2—W1	1.9315 (17)	C33—N5	1.521 (2)
C3—O3	1.1978 (19)	C33—H33A	0.9900
C3—W1	1.9261 (17)	C33—H33B	0.9900
C4—O4	1.196 (2)	C34—H34A	0.9800
C4—W2	1.9275 (17)	C34—H34B	0.9800
C5—O5	1.1908 (19)	C34—H34C	0.9800
C5—W2	1.9267 (16)	C35—C36	1.504 (2)
C6—O6	1.2002 (19)	C35—N5	1.518 (2)
C6—W2	1.9201 (16)	C35—H35A	0.9900
C7—O7	1.4021 (18)	C35—H35B	0.9900
C7—C8	1.512 (2)	C36—H36A	0.9800
C7—H7A	0.9900	C36—H36B	0.9800
C7—H7B	0.9900	C36—H36C	0.9800
C8—C9	1.390 (2)	C37—C38	1.513 (3)
C8—C12	1.392 (2)	C37—N5	1.519 (2)
C9—C10	1.395 (2)	C37—H37A	0.9900
C9—H9	0.9500	C37—H37B	0.9900
C10—N1	1.339 (3)	C38—H38A	0.9800
C10—H10	0.9500	C38—H38B	0.9800
C11—N1	1.335 (3)	C38—H38C	0.9800
C11—C12	1.386 (3)	C39—N5	1.520 (2)
C11—H11	0.9500	C39—C40	1.519 (2)
C12—H12	0.9500	C39—H39A	0.9900
C13—O8	1.3935 (18)	C39—H39B	0.9900
C13—C14	1.517 (2)	C40—H40A	0.9800
C13—H13A	0.9900	C40—H40B	0.9800
C13—H13B	0.9900	C40—H40C	0.9800
C14—C18	1.390 (2)	C41—C42	1.513 (2)
C14—C15	1.398 (2)	C41—N6	1.513 (2)
C15—C16	1.384 (2)	C41—H41A	0.9900
C15—H15	0.9500	C41—H41B	0.9900
C16—N2	1.335 (2)	C42—H42A	0.9800
C16—H16	0.9500	C42—H42B	0.9800
C17—N2	1.341 (2)	C42—H42C	0.9800
C17—C18	1.388 (2)	C43—C44	1.515 (2)
C17—H17	0.9500	C43—N6	1.520 (2)
C18—H18	0.9500	C43—H43A	0.9900
C19—O9	1.3917 (19)	C43—H43B	0.9900
C19—C20	1.506 (2)	C44—H44A	0.9800
C19—H19A	0.9900	C44—H44B	0.9800
C19—H19B	0.9900	C44—H44C	0.9800
C20—C21	1.385 (2)	C45—C46	1.513 (3)
C20—C24	1.398 (2)	C45—N6	1.520 (2)
C21—C22	1.394 (3)	C45—H45A	0.9900
C21—H21	0.9500	C45—H45B	0.9900
C22—N3	1.335 (3)	C46—H46A	0.9800
C22—H22	0.9500	C46—H46B	0.9800
C23—N3	1.336 (3)	C46—H46C	0.9800
C23—C24	1.379 (3)	C47—C48	1.505 (3)
C23—H23	0.9500	C47—N6	1.516 (2)
C24—H24	0.9500	C47—H47A	0.9900
C25—C26	1.512 (2)	C47—H47B	0.9900
C25—N4	1.521 (2)	C48—H48A	0.9800
C25—H25A	0.9900	C48—H48B	0.9800
C25—H25B	0.9900	C48—H48C	0.9800
C26—H26A	0.9800	C49—N7	1.138 (3)
C26—H26B	0.9800	C49—C50	1.457 (3)
C26—H26C	0.9800	C50—H50A	0.9800
C27—C28	1.516 (2)	C50—H50B	0.9800
C27—N4	1.519 (2)	C50—H50C	0.9800
C27—H27A	0.9900	C51—N8	1.142 (3)
C27—H27B	0.9900	C51—C52	1.453 (3)
C28—H28A	0.9800	C52—H52A	0.9800
C28—H28B	0.9800	C52—H52B	0.9800
C28—H28C	0.9800	C52—H52C	0.9800
C29—N4	1.516 (2)	C53—N9	1.141 (3)
C29—C30	1.521 (2)	C53—C54	1.444 (4)
C29—H29A	0.9900	C54—H54A	0.9800
C29—H29B	0.9900	C54—H54B	0.9800
C30—H30A	0.9800	C54—H54C	0.9800
C30—H30B	0.9800	O7—W2	2.2311 (11)
C30—H30C	0.9800	O7—W1	2.2352 (11)
C31—C32	1.515 (2)	O8—W1	2.1660 (10)
C31—N4	1.520 (2)	O8—W2	2.1683 (10)
C31—H31A	0.9900	O9—W1	2.1930 (11)
C31—H31B	0.9900	O9—W2	2.1937 (11)
C32—H32A	0.9800
O1—C1—W1	176.56 (14)	C37—C38—H38A	109.5
O2—C2—W1	175.93 (15)	C37—C38—H38B	109.5
O3—C3—W1	176.46 (14)	H38A—C38—H38B	109.5
O4—C4—W2	178.54 (14)	C37—C38—H38C	109.5
O5—C5—W2	176.62 (14)	H38A—C38—H38C	109.5
O6—C6—W2	176.29 (14)	H38B—C38—H38C	109.5
O7—C7—C8	113.71 (13)	N5—C39—C40	114.90 (14)
O7—C7—H7A	108.8	N5—C39—H39A	108.5
C8—C7—H7A	108.8	C40—C39—H39A	108.5
O7—C7—H7B	108.8	N5—C39—H39B	108.5
C8—C7—H7B	108.8	C40—C39—H39B	108.5
H7A—C7—H7B	107.7	H39A—C39—H39B	107.5
C9—C8—C12	117.08 (16)	C39—C40—H40A	109.5
C9—C8—C7	122.46 (15)	C39—C40—H40B	109.5
C12—C8—C7	120.39 (16)	H40A—C40—H40B	109.5
C8—C9—C10	119.00 (17)	C39—C40—H40C	109.5
C8—C9—H9	120.5	H40A—C40—H40C	109.5
C10—C9—H9	120.5	H40B—C40—H40C	109.5
N1—C10—C9	124.37 (19)	C42—C41—N6	115.60 (15)
N1—C10—H10	117.8	C42—C41—H41A	108.4
C9—C10—H10	117.8	N6—C41—H41A	108.4
N1—C11—C12	124.52 (18)	C42—C41—H41B	108.4
N1—C11—H11	117.7	N6—C41—H41B	108.4
C12—C11—H11	117.7	H41A—C41—H41B	107.4
C11—C12—C8	119.35 (19)	C41—C42—H42A	109.5
C11—C12—H12	120.3	C41—C42—H42B	109.5
C8—C12—H12	120.3	H42A—C42—H42B	109.5
O8—C13—C14	112.71 (13)	C41—C42—H42C	109.5
O8—C13—H13A	109.0	H42A—C42—H42C	109.5
C14—C13—H13A	109.0	H42B—C42—H42C	109.5
O8—C13—H13B	109.0	C44—C43—N6	115.48 (14)
C14—C13—H13B	109.0	C44—C43—H43A	108.4
H13A—C13—H13B	107.8	N6—C43—H43A	108.4
C18—C14—C15	117.29 (15)	C44—C43—H43B	108.4
C18—C14—C13	121.73 (14)	N6—C43—H43B	108.4
C15—C14—C13	120.99 (15)	H43A—C43—H43B	107.5
C16—C15—C14	118.87 (16)	C43—C44—H44A	109.5
C16—C15—H15	120.6	C43—C44—H44B	109.5
C14—C15—H15	120.6	H44A—C44—H44B	109.5
N2—C16—C15	124.68 (16)	C43—C44—H44C	109.5
N2—C16—H16	117.7	H44A—C44—H44C	109.5
C15—C16—H16	117.7	H44B—C44—H44C	109.5
N2—C17—C18	124.25 (17)	C46—C45—N6	114.43 (16)
N2—C17—H17	117.9	C46—C45—H45A	108.7
C18—C17—H17	117.9	N6—C45—H45A	108.7
C17—C18—C14	119.12 (15)	C46—C45—H45B	108.7
C17—C18—H18	120.4	N6—C45—H45B	108.7
C14—C18—H18	120.4	H45A—C45—H45B	107.6
O9—C19—C20	113.29 (13)	C45—C46—H46A	109.5
O9—C19—H19A	108.9	C45—C46—H46B	109.5
C20—C19—H19A	108.9	H46A—C46—H46B	109.5
O9—C19—H19B	108.9	C45—C46—H46C	109.5
C20—C19—H19B	108.9	H46A—C46—H46C	109.5
H19A—C19—H19B	107.7	H46B—C46—H46C	109.5
C21—C20—C24	117.31 (16)	C48—C47—N6	115.52 (18)
C21—C20—C19	121.77 (15)	C48—C47—H47A	108.4
C24—C20—C19	120.92 (15)	N6—C47—H47A	108.4
C20—C21—C22	118.76 (17)	C48—C47—H47B	108.4
C20—C21—H21	120.6	N6—C47—H47B	108.4
C22—C21—H21	120.6	H47A—C47—H47B	107.5
N3—C22—C21	124.44 (19)	C47—C48—H48A	109.5
N3—C22—H22	117.8	C47—C48—H48B	109.5
C21—C22—H22	117.8	H48A—C48—H48B	109.5
N3—C23—C24	124.31 (18)	C47—C48—H48C	109.5
N3—C23—H23	117.8	H48A—C48—H48C	109.5
C24—C23—H23	117.8	H48B—C48—H48C	109.5
C23—C24—C20	119.28 (17)	N7—C49—C50	179.0 (2)
C23—C24—H24	120.4	C49—C50—H50A	109.5
C20—C24—H24	120.4	C49—C50—H50B	109.5
C26—C25—N4	115.34 (14)	H50A—C50—H50B	109.5
C26—C25—H25A	108.4	C49—C50—H50C	109.5
N4—C25—H25A	108.4	H50A—C50—H50C	109.5
C26—C25—H25B	108.4	H50B—C50—H50C	109.5
N4—C25—H25B	108.4	N8—C51—C52	178.9 (2)
H25A—C25—H25B	107.5	C51—C52—H52A	109.5
C25—C26—H26A	109.5	C51—C52—H52B	109.5
C25—C26—H26B	109.5	H52A—C52—H52B	109.5
H26A—C26—H26B	109.5	C51—C52—H52C	109.5
C25—C26—H26C	109.5	H52A—C52—H52C	109.5
H26A—C26—H26C	109.5	H52B—C52—H52C	109.5
H26B—C26—H26C	109.5	N9—C53—C54	178.8 (3)
C28—C27—N4	114.78 (15)	C53—C54—H54A	109.5
C28—C27—H27A	108.6	C53—C54—H54B	109.5
N4—C27—H27A	108.6	H54A—C54—H54B	109.5
C28—C27—H27B	108.6	C53—C54—H54C	109.5
N4—C27—H27B	108.6	H54A—C54—H54C	109.5
H27A—C27—H27B	107.5	H54B—C54—H54C	109.5
C27—C28—H28A	109.5	C11—N1—C10	115.65 (17)
C27—C28—H28B	109.5	C16—N2—C17	115.79 (15)
H28A—C28—H28B	109.5	C22—N3—C23	115.90 (16)
C27—C28—H28C	109.5	C29—N4—C27	112.25 (13)
H28A—C28—H28C	109.5	C29—N4—C31	108.27 (13)
H28B—C28—H28C	109.5	C27—N4—C31	108.10 (13)
N4—C29—C30	115.40 (15)	C29—N4—C25	108.17 (13)
N4—C29—H29A	108.4	C27—N4—C25	108.51 (13)
C30—C29—H29A	108.4	C31—N4—C25	111.60 (13)
N4—C29—H29B	108.4	C35—N5—C37	105.61 (13)
C30—C29—H29B	108.4	C35—N5—C33	111.43 (13)
H29A—C29—H29B	107.5	C37—N5—C33	111.26 (13)
C29—C30—H30A	109.5	C35—N5—C39	110.97 (13)
C29—C30—H30B	109.5	C37—N5—C39	111.71 (13)
H30A—C30—H30B	109.5	C33—N5—C39	105.98 (12)
C29—C30—H30C	109.5	C41—N6—C47	111.33 (14)
H30A—C30—H30C	109.5	C41—N6—C45	110.59 (13)
H30B—C30—H30C	109.5	C47—N6—C45	106.14 (15)
C32—C31—N4	114.83 (14)	C41—N6—C43	106.07 (13)
C32—C31—H31A	108.6	C47—N6—C43	111.70 (13)
N4—C31—H31A	108.6	C45—N6—C43	111.10 (13)
C32—C31—H31B	108.6	C7—O7—W2	118.79 (9)
N4—C31—H31B	108.6	C7—O7—W1	120.87 (9)
H31A—C31—H31B	107.5	W2—O7—W1	93.62 (4)
C31—C32—H32A	109.5	C13—O8—W1	127.33 (9)
C31—C32—H32B	109.5	C13—O8—W2	129.49 (10)
H32A—C32—H32B	109.5	W1—O8—W2	97.41 (4)
C31—C32—H32C	109.5	C19—O9—W1	124.85 (10)
H32A—C32—H32C	109.5	C19—O9—W2	127.06 (9)
H32B—C32—H32C	109.5	W1—O9—W2	95.86 (4)
C34—C33—N5	115.13 (14)	C1—W1—C3	82.30 (7)
C34—C33—H33A	108.5	C1—W1—C2	82.52 (7)
N5—C33—H33A	108.5	C3—W1—C2	88.96 (7)
C34—C33—H33B	108.5	C1—W1—O8	102.67 (6)
N5—C33—H33B	108.5	C3—W1—O8	100.90 (5)
H33A—C33—H33B	107.5	C2—W1—O8	169.34 (5)
C33—C34—H34A	109.5	C1—W1—O9	102.64 (6)
C33—C34—H34B	109.5	C3—W1—O9	170.15 (5)
H34A—C34—H34B	109.5	C2—W1—O9	100.07 (6)
C33—C34—H34C	109.5	O8—W1—O9	69.83 (4)
H34A—C34—H34C	109.5	C1—W1—O7	172.90 (5)
H34B—C34—H34C	109.5	C3—W1—O7	101.57 (6)
C36—C35—N5	115.95 (14)	C2—W1—O7	103.38 (5)
C36—C35—H35A	108.3	O8—W1—O7	70.87 (4)
N5—C35—H35A	108.3	O9—W1—O7	72.65 (4)
C36—C35—H35B	108.3	C6—W2—C5	83.33 (7)
N5—C35—H35B	108.3	C6—W2—C4	83.52 (7)
H35A—C35—H35B	107.4	C5—W2—C4	89.06 (7)
C35—C36—H36A	109.5	C6—W2—O8	105.52 (5)
C35—C36—H36B	109.5	C5—W2—O8	166.31 (5)
H36A—C36—H36B	109.5	C4—W2—O8	102.14 (5)
C35—C36—H36C	109.5	C6—W2—O9	102.35 (6)
H36A—C36—H36C	109.5	C5—W2—O9	98.42 (5)
H36B—C36—H36C	109.5	C4—W2—O9	170.93 (5)
C38—C37—N5	114.51 (14)	O8—W2—O9	69.77 (4)
C38—C37—H37A	108.6	C6—W2—O7	174.59 (5)
N5—C37—H37A	108.6	C5—W2—O7	99.45 (5)
C38—C37—H37B	108.6	C4—W2—O7	101.10 (5)
N5—C37—H37B	108.6	O8—W2—O7	70.90 (4)
H37A—C37—H37B	107.6	O9—W2—O7	72.72 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C54—H54B···O7^i	0.98	2.40	3.378 (3)	174
C27—H27B···N1^ii	0.99	2.69	3.578 (3)	149
C27—H27A···N3	0.99	2.60	3.464 (2)	146
C43—H43B···N1^ii	0.99	2.54	3.521 (2)	173
C50—H50A···N2	0.98	2.62	3.423 (2)	139
C52—H52A···N2^iii	0.98	2.62	3.483 (3)	148
C25—H25A···N3	0.99	2.64	3.470 (2)	141

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