Tetra­kis(μ2-3,4-dimethoxy­phenyl­acetato)-κ3O,O′:O′;κ3O:O:O′;κ2O:O′;κ2O:O′-bis­[(3,4-dimethoxy­phenyl­acetato-κ2O,O′)(1,10-phenanthroline-κ2N,N)thulium(III)]

Liu, J.-L.; Li, H.-Q.; Zhao, G.-L.

doi:10.1107/S1600536809051435

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page m9

doi:10.1107/S1600536809051435

Open

access

Tetrakis(μ₂-3,4-dimethoxyphenylacetato)-κ³O,O′:O′;κ³O:O:O′;κ²O:O′;κ²O:O′-bis[(3,4-dimethoxyphenylacetato-κ²O,O′)(1,10-phenanthroline-κ²N,N)thulium(III)]

Jia-Lu Liu,^a Hua-Qiong Li ^a and Guo-Liang Zhao ^a ^*

^aZhejiang Key Laboratory for Reactive Chemistry on Solid Surfaces, Institute of Physical Chemistry, Zhejiang Normal University, Jinhua, Zhejiang 321004, People's Republic of China, and College of Chemistry and Life Science, Zhejiang Normal University, Jinhua 321004, Zhejiang, People's Republic of China
^*Correspondence e-mail: sky53@zjnu.cn

(Received 13 November 2009; accepted 29 November 2009; online 4 December 2009)

In the title centrosymmetric dinuclear complex, [Tm₂(C₁₀H₁₁O₄)₆(C₁₂H₈N₂)₂], the unique Tm^III ion is coordinated by five 3,4-dimethoxyphenylacetate (DMPA) ligands and and a bis-chelating 1,10-phenanthroline (phen) ligand via seven O atoms and two N atoms, forming a distorted tricapped trigonal-prismatic environment. The DMPA ligands coordinate in the bis-chelate, bridging and bridging tridentate modes.

Related literature

For background to the importance of coordination in magnetism, see: Yao et al. (2008 ); Fang & Zhang (2006 ); Li et al. 2008 ); Wang & Sevov (2008 ). For a related structure, see: Wang et al. (2008 ).

Experimental

Crystal data

[Tm₂(C₁₀H₁₁O₄)₆(C₁₂H₈N₂)₂]
M_r = 1869.40
Triclinic, $[P \overline 1]$
a = 12.3025 (1) Å
b = 12.3483 (2) Å
c = 14.5883 (2) Å
α = 91.457 (1)°
β = 103.403 (1)°
γ = 114.406 (1)°
V = 1944.71 (4) Å³
Z = 1
Mo Kα radiation
μ = 2.35 mm⁻¹
T = 296 K
0.35 × 0.11 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.747, T_max = 0.798
32353 measured reflections
6861 independent reflections
5961 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.025
wR(F²) = 0.058
S = 1.03
6861 reflections
514 parameters
H-atom parameters constrained
Δρ_max = 0.64 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1999 ); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809051435/lh2956sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809051435/lh2956Isup2.hkl

checkCIF report

Comment top

In recently years, there has been an increasing interest in coordination chemistry due to the increased recognition of of it's importance in magnetism (Yao, et al., 2008; Fang, et al., 2006; Wang, et al., 2008) and this has attracted our interest (Li, et al., 2008). Here we report the crystal structure of a new thulium(III) complex with the ligand 3,4-dimethoxyphenylacetate. In the title dinuclear complex (I), the unique Tm^III ion is coordinated by five DMPA ligands and a phen ligand via seven O atoms and two N atoms (see, Fig. 1). The Tm^III ion is in a distorted tricapped trigonal prismatic environment. The DMPA ligands coordinate in the bis-chelate, bridging and bridging tridentate modes.

Related literature top

For background to the importance of coordination in magnetism, see: Yao et al. (2008); Fang et al. (2006); Li et al. 2008); Wang & Sevov (2008). For a related structure, see: Wang et al. (2008).

Experimental top

All reagents and solvents were commercially available quality and without purified before using. The title compound was obtained by adding Tm₂O₃ (0.5 mmol), homoveratric acid (3 mmol) phen (1 mmol) dissolved in 30 ml water, sealed in a 50 ml stainless steel reactor and kept three days at temperature of 433 K. Then, the reactor was cooled to room temperature at a speed of 5 degrees per hour. Filtrate the solution, washing deposition with ethanol, then colorless histogram crystals can be attained.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title complex. Displacement ellipsoids are drawn at the 30% probability level. Unlabeled atoms are related by the symmetry operator (-x, -y, -z).

Tetrakis(µ₂-3,4-dimethoxyphenylacetato)-κ³O,O':O'; κ³O:O:O';κ²O:O'; κ²O:O'-bis[(3,4-dimethoxyphenylacetato- κ²O,O')(1,10-phenanthroline- κ²N,N)thulium(III)] top

Crystal data top

[Tm₂(C₁₀H₁₁O₄)₆(C₁₂H₈N₂)₂]	Z = 1
M_r = 1869.40	F(000) = 944
Triclinic, P1	D_x = 1.596 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 12.3025 (1) Å	Cell parameters from 8597 reflections
b = 12.3483 (2) Å	θ = 2.1–27.6°
c = 14.5883 (2) Å	µ = 2.35 mm⁻¹
α = 91.457 (1)°	T = 296 K
β = 103.403 (1)°	Block, colourless
γ = 114.406 (1)°	0.35 × 0.11 × 0.10 mm
V = 1944.71 (4) Å³

Data collection top

Bruker SMART APEX diffractometer	6861 independent reflections
Radiation source: fine-focus sealed tube	5961 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
ω scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
T_min = 0.747, T_max = 0.798	k = −14→14
32353 measured reflections	l = −17→17

Refinement top

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.058	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0303P)² + 0.071P] where P = (F_o² + 2F_c²)/3
6861 reflections	(Δ/σ)_max = 0.004
514 parameters	Δρ_max = 0.64 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

[Tm₂(C₁₀H₁₁O₄)₆(C₁₂H₈N₂)₂]	γ = 114.406 (1)°
M_r = 1869.40	V = 1944.71 (4) Å³
Triclinic, P1	Z = 1
a = 12.3025 (1) Å	Mo Kα radiation
b = 12.3483 (2) Å	µ = 2.35 mm⁻¹
c = 14.5883 (2) Å	T = 296 K
α = 91.457 (1)°	0.35 × 0.11 × 0.10 mm
β = 103.403 (1)°

Data collection top

Bruker SMART APEX diffractometer	6861 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	5961 reflections with I > 2σ(I)
T_min = 0.747, T_max = 0.798	R_int = 0.038
32353 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	0 restraints
wR(F²) = 0.058	H-atom parameters constrained
S = 1.03	Δρ_max = 0.64 e Å⁻³
6861 reflections	Δρ_min = −0.32 e Å⁻³
514 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
Tm1	0.175028 (11)	0.102013 (13)	0.030650 (9)	0.04097 (6)
N1	0.3561 (2)	0.1554 (2)	0.18114 (19)	0.0465 (6)
O1	0.3698 (2)	−0.4441 (2)	0.30577 (16)	0.0521 (6)
C1	0.3391 (4)	−0.5686 (3)	0.2846 (3)	0.0632 (10)
H1A	0.3974	−0.5884	0.3283	0.095*
H1B	0.3422	−0.5848	0.2208	0.095*
H1C	0.2572	−0.6161	0.2905	0.095*
O2	0.3894 (2)	−0.2368 (2)	0.36761 (18)	0.0685 (7)
N2	0.3785 (2)	0.1373 (2)	0.0008 (2)	0.0496 (7)
C2	0.2942 (3)	−0.4026 (3)	0.2490 (2)	0.0413 (7)
O3	0.01233 (18)	−0.0982 (2)	0.04225 (14)	0.0462 (5)
C3	0.2150 (3)	−0.4601 (3)	0.1623 (2)	0.0512 (8)
H3A	0.2115	−0.5318	0.1373	0.061*
O4	0.20449 (19)	−0.0728 (2)	0.08331 (16)	0.0487 (5)
C4	0.1394 (3)	−0.4117 (3)	0.1114 (3)	0.0581 (9)
H4A	0.0872	−0.4512	0.0519	0.070*
O5	0.2337 (3)	0.5128 (3)	−0.43218 (19)	0.0821 (8)
C5	0.1398 (3)	−0.3071 (3)	0.1466 (2)	0.0460 (8)
C6	0.2248 (3)	−0.2465 (3)	0.2326 (2)	0.0451 (8)
H6A	0.2297	−0.1737	0.2565	0.054*
O6	0.1019 (2)	0.5544 (3)	−0.3365 (2)	0.0800 (8)
O7	0.21737 (19)	0.2421 (2)	−0.08600 (15)	0.0469 (5)
C7	0.3022 (3)	−0.2915 (3)	0.2833 (2)	0.0435 (7)
O8	0.2591 (2)	0.3120 (2)	0.06308 (15)	0.0555 (6)
C8	0.4180 (4)	−0.1159 (4)	0.3958 (3)	0.0852 (14)
H8A	0.4800	−0.0874	0.4556	0.128*
H8B	0.3447	−0.1099	0.4022	0.128*
H8C	0.4488	−0.0682	0.3486	0.128*
C9	0.0460 (3)	−0.2642 (3)	0.0961 (3)	0.0550 (9)
H9A	−0.0017	−0.3175	0.0369	0.066*
H9B	−0.0107	−0.2735	0.1349	0.066*
O9	−0.2502 (3)	−0.0455 (3)	−0.5655 (2)	0.0980 (10)
C10	0.0931 (3)	−0.1378 (3)	0.0735 (2)	0.0416 (7)
O10	−0.1572 (3)	0.1810 (3)	−0.5085 (2)	0.0848 (9)
O11	0.11190 (19)	−0.0205 (2)	−0.11245 (15)	0.0470 (5)
C11	0.3103 (5)	0.5021 (5)	−0.4862 (3)	0.1033 (16)
H11C	0.2831	0.5165	−0.5499	0.155*
H11D	0.3060	0.4226	−0.4875	0.155*
H11A	0.3942	0.5598	−0.4581	0.155*
C12	0.2587 (3)	0.4949 (3)	−0.3385 (2)	0.0576 (9)
O12	−0.09479 (19)	−0.1233 (2)	−0.15456 (15)	0.0523 (6)
C13	0.3461 (3)	0.4592 (3)	−0.2948 (3)	0.0625 (10)
H13A	0.3935	0.4427	−0.3294	0.075*
C14	0.3652 (3)	0.4470 (3)	−0.1987 (3)	0.0633 (10)
H14A	0.4253	0.4227	−0.1693	0.076*
C15	0.2951 (3)	0.4710 (3)	−0.1466 (2)	0.0534 (9)
C16	0.2053 (3)	0.5051 (3)	−0.1922 (3)	0.0569 (9)
H16A	0.1564	0.5194	−0.1580	0.068*
C17	0.1865 (3)	0.5185 (3)	−0.2867 (3)	0.0564 (9)
C18	0.0160 (4)	0.5660 (4)	−0.2907 (4)	0.0914 (14)
H18A	−0.0379	0.5918	−0.3334	0.137*
H18B	0.0602	0.6242	−0.2347	0.137*
H18C	−0.0322	0.4899	−0.2733	0.137*
C19	0.3135 (4)	0.4569 (3)	−0.0425 (3)	0.0640 (10)
H19A	0.2760	0.4999	−0.0144	0.077*
H19B	0.4015	0.4944	−0.0115	0.077*
C20	0.2600 (3)	0.3284 (3)	−0.0220 (2)	0.0456 (8)
C21	−0.2939 (5)	−0.1633 (5)	−0.6054 (3)	0.1053 (17)
H21A	−0.3540	−0.1780	−0.6652	0.158*
H21B	−0.3319	−0.2160	−0.5633	0.158*
H21C	−0.2263	−0.1776	−0.6155	0.158*
C22	−0.1625 (3)	−0.0060 (4)	−0.4787 (3)	0.0617 (10)
C23	−0.1222 (3)	−0.0781 (3)	−0.4219 (3)	0.0585 (9)
H23A	−0.1556	−0.1601	−0.4422	0.070*
C24	−0.0336 (3)	−0.0302 (3)	−0.3362 (2)	0.0488 (8)
C25	0.0151 (3)	0.0914 (3)	−0.3078 (2)	0.0594 (9)
H25A	0.0751	0.1250	−0.2501	0.071*
C26	−0.0237 (4)	0.1647 (4)	−0.3637 (3)	0.0667 (10)
H26A	0.0107	0.2468	−0.3437	0.080*
C27	−0.1136 (3)	0.1156 (4)	−0.4491 (2)	0.0602 (10)
C28	−0.1058 (5)	0.3062 (5)	−0.4796 (4)	0.1056 (17)
H28A	−0.1433	0.3422	−0.5267	0.158*
H28B	−0.0181	0.3405	−0.4726	0.158*
H28C	−0.1210	0.3206	−0.4199	0.158*
C29	0.0109 (3)	−0.1085 (3)	−0.2735 (2)	0.0544 (9)
H29A	−0.0424	−0.1925	−0.2975	0.065*
H29B	0.0943	−0.0927	−0.2755	0.065*
C30	0.0095 (3)	−0.0830 (3)	−0.1716 (2)	0.0459 (8)
C31	0.3467 (3)	0.1640 (3)	0.2691 (2)	0.0534 (9)
H31A	0.2728	0.1600	0.2779	0.064*
C32	0.4414 (3)	0.1785 (3)	0.3499 (3)	0.0617 (10)
H32A	0.4311	0.1860	0.4105	0.074*
C33	0.5489 (3)	0.1816 (3)	0.3375 (3)	0.0645 (10)
H33A	0.6129	0.1906	0.3901	0.077*
C34	0.5632 (3)	0.1712 (3)	0.2472 (3)	0.0549 (9)
C35	0.6728 (3)	0.1718 (3)	0.2281 (4)	0.0746 (12)
H35A	0.7371	0.1761	0.2786	0.089*
C36	0.6844 (3)	0.1663 (4)	0.1397 (4)	0.0761 (13)
H36A	0.7570	0.1673	0.1302	0.091*
C37	0.5883 (3)	0.1588 (3)	0.0593 (3)	0.0592 (10)
C38	0.5985 (3)	0.1566 (3)	−0.0335 (3)	0.0713 (12)
H38A	0.6712	0.1615	−0.0457	0.086*
C39	0.5023 (4)	0.1473 (4)	−0.1062 (3)	0.0726 (12)
H39A	0.5090	0.1484	−0.1684	0.087*
C40	0.3922 (3)	0.1361 (3)	−0.0859 (3)	0.0600 (10)
H40A	0.3258	0.1273	−0.1363	0.072*
C41	0.4763 (3)	0.1515 (3)	0.0748 (3)	0.0485 (8)
C42	0.4642 (3)	0.1595 (3)	0.1689 (2)	0.0442 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Tm1	0.04263 (9)	0.06291 (11)	0.03925 (9)	0.03882 (7)	0.01862 (6)	0.02181 (7)
N1	0.0437 (14)	0.0538 (17)	0.0553 (18)	0.0325 (13)	0.0142 (12)	0.0189 (14)
O1	0.0606 (14)	0.0536 (14)	0.0516 (14)	0.0386 (12)	0.0048 (11)	0.0131 (11)
C1	0.085 (3)	0.066 (2)	0.058 (2)	0.055 (2)	0.0112 (19)	0.0174 (19)
O2	0.0852 (18)	0.0539 (16)	0.0568 (16)	0.0380 (14)	−0.0132 (13)	0.0011 (13)
N2	0.0496 (15)	0.0606 (18)	0.0589 (18)	0.0355 (14)	0.0275 (14)	0.0227 (14)
C2	0.0425 (16)	0.052 (2)	0.0419 (18)	0.0303 (15)	0.0132 (14)	0.0166 (15)
O3	0.0473 (12)	0.0716 (15)	0.0467 (13)	0.0461 (11)	0.0211 (10)	0.0259 (11)
C3	0.062 (2)	0.057 (2)	0.048 (2)	0.0425 (18)	0.0064 (16)	0.0029 (17)
O4	0.0422 (12)	0.0622 (14)	0.0601 (14)	0.0369 (11)	0.0178 (10)	0.0243 (12)
C4	0.058 (2)	0.064 (2)	0.053 (2)	0.0375 (19)	−0.0061 (16)	0.0000 (18)
O5	0.093 (2)	0.117 (2)	0.0538 (16)	0.0547 (18)	0.0318 (15)	0.0371 (16)
C5	0.0411 (17)	0.049 (2)	0.055 (2)	0.0275 (15)	0.0089 (15)	0.0168 (16)
C6	0.0489 (18)	0.0406 (18)	0.054 (2)	0.0255 (15)	0.0155 (15)	0.0158 (16)
O6	0.0758 (18)	0.102 (2)	0.086 (2)	0.0550 (17)	0.0296 (15)	0.0426 (17)
O7	0.0538 (13)	0.0596 (15)	0.0419 (13)	0.0341 (12)	0.0197 (10)	0.0159 (12)
C7	0.0472 (17)	0.0441 (19)	0.0422 (18)	0.0235 (15)	0.0095 (14)	0.0116 (15)
O8	0.0776 (16)	0.0684 (16)	0.0387 (13)	0.0454 (13)	0.0210 (11)	0.0209 (12)
C8	0.097 (3)	0.060 (3)	0.080 (3)	0.039 (2)	−0.015 (2)	−0.010 (2)
C9	0.0455 (18)	0.055 (2)	0.070 (2)	0.0310 (17)	0.0078 (16)	0.0166 (18)
O9	0.101 (2)	0.092 (2)	0.078 (2)	0.0443 (19)	−0.0206 (18)	−0.0066 (18)
C10	0.0466 (18)	0.063 (2)	0.0347 (17)	0.0405 (17)	0.0144 (13)	0.0146 (15)
O10	0.101 (2)	0.086 (2)	0.0683 (19)	0.0523 (18)	0.0012 (16)	0.0217 (16)
O11	0.0476 (13)	0.0688 (15)	0.0452 (13)	0.0393 (12)	0.0220 (11)	0.0189 (11)
C11	0.141 (4)	0.134 (4)	0.055 (3)	0.067 (4)	0.046 (3)	0.034 (3)
C12	0.064 (2)	0.066 (2)	0.047 (2)	0.0271 (19)	0.0227 (17)	0.0229 (18)
O12	0.0468 (12)	0.0839 (17)	0.0425 (13)	0.0401 (12)	0.0180 (10)	0.0170 (12)
C13	0.067 (2)	0.073 (3)	0.063 (2)	0.035 (2)	0.0336 (19)	0.019 (2)
C14	0.069 (2)	0.074 (3)	0.059 (2)	0.042 (2)	0.0185 (19)	0.027 (2)
C15	0.066 (2)	0.048 (2)	0.048 (2)	0.0207 (17)	0.0237 (17)	0.0157 (17)
C16	0.066 (2)	0.055 (2)	0.060 (2)	0.0282 (18)	0.0294 (18)	0.0185 (18)
C17	0.061 (2)	0.055 (2)	0.060 (2)	0.0288 (18)	0.0206 (18)	0.0229 (18)
C18	0.075 (3)	0.101 (4)	0.121 (4)	0.053 (3)	0.036 (3)	0.033 (3)
C19	0.077 (3)	0.064 (2)	0.048 (2)	0.025 (2)	0.0199 (18)	0.0160 (19)
C20	0.0430 (17)	0.065 (2)	0.043 (2)	0.0352 (17)	0.0141 (14)	0.0178 (18)
C21	0.091 (3)	0.126 (5)	0.073 (3)	0.040 (3)	−0.008 (3)	−0.024 (3)
C22	0.060 (2)	0.076 (3)	0.048 (2)	0.032 (2)	0.0076 (17)	0.013 (2)
C23	0.058 (2)	0.064 (2)	0.054 (2)	0.0277 (19)	0.0145 (17)	0.0062 (19)
C24	0.0536 (19)	0.071 (3)	0.0369 (18)	0.0351 (18)	0.0225 (15)	0.0174 (17)
C25	0.070 (2)	0.066 (3)	0.041 (2)	0.033 (2)	0.0074 (17)	0.0117 (18)
C26	0.082 (3)	0.063 (2)	0.052 (2)	0.032 (2)	0.011 (2)	0.0130 (19)
C27	0.067 (2)	0.073 (3)	0.044 (2)	0.035 (2)	0.0110 (17)	0.019 (2)
C28	0.132 (4)	0.086 (4)	0.097 (4)	0.053 (3)	0.013 (3)	0.040 (3)
C29	0.066 (2)	0.075 (2)	0.046 (2)	0.046 (2)	0.0266 (16)	0.0155 (18)
C30	0.054 (2)	0.066 (2)	0.0426 (18)	0.0442 (18)	0.0218 (16)	0.0221 (17)
C31	0.054 (2)	0.064 (2)	0.054 (2)	0.0370 (18)	0.0136 (16)	0.0200 (18)
C32	0.065 (2)	0.067 (2)	0.054 (2)	0.035 (2)	0.0039 (18)	0.0174 (19)
C33	0.057 (2)	0.057 (2)	0.068 (3)	0.0271 (19)	−0.0076 (19)	0.009 (2)
C34	0.0394 (18)	0.0397 (19)	0.081 (3)	0.0204 (15)	0.0012 (17)	0.0059 (18)
C35	0.0370 (19)	0.060 (3)	0.114 (4)	0.0225 (18)	−0.004 (2)	−0.005 (3)
C36	0.0330 (19)	0.065 (3)	0.131 (4)	0.0257 (18)	0.016 (2)	−0.002 (3)
C37	0.0403 (18)	0.047 (2)	0.104 (3)	0.0265 (16)	0.0279 (19)	0.010 (2)
C38	0.049 (2)	0.063 (2)	0.120 (4)	0.0294 (19)	0.046 (2)	0.010 (2)
C39	0.073 (3)	0.076 (3)	0.097 (3)	0.041 (2)	0.055 (2)	0.023 (2)
C40	0.059 (2)	0.074 (3)	0.071 (3)	0.042 (2)	0.0354 (19)	0.024 (2)
C41	0.0388 (17)	0.0427 (19)	0.074 (2)	0.0238 (15)	0.0208 (16)	0.0148 (17)
C42	0.0380 (16)	0.0388 (18)	0.065 (2)	0.0244 (14)	0.0142 (15)	0.0163 (16)

Geometric parameters (Å, º) top

Tm1—O3ⁱ	2.2840 (18)	C12—C17	1.399 (5)
Tm1—O12ⁱ	2.308 (2)	O12—C30	1.258 (4)
Tm1—O11	2.317 (2)	O12—Tm1ⁱ	2.308 (2)
Tm1—O8	2.348 (2)	C13—C14	1.389 (5)
Tm1—O7	2.444 (2)	C13—H13A	0.9300
Tm1—O4	2.4459 (19)	C14—C15	1.382 (5)
Tm1—O3	2.497 (2)	C14—H14A	0.9300
Tm1—N2	2.502 (2)	C15—C16	1.378 (5)
Tm1—N1	2.581 (2)	C15—C19	1.508 (5)
Tm1—C20	2.750 (3)	C16—C17	1.371 (5)
Tm1—C10	2.846 (3)	C16—H16A	0.9300
Tm1—Tm1ⁱ	3.8506 (3)	C18—H18A	0.9600
N1—C31	1.321 (4)	C18—H18B	0.9600
N1—C42	1.363 (4)	C18—H18C	0.9600
O1—C2	1.367 (3)	C19—C20	1.514 (5)
O1—C1	1.430 (4)	C19—H19A	0.9700
C1—H1A	0.9600	C19—H19B	0.9700
C1—H1B	0.9600	C21—H21A	0.9600
C1—H1C	0.9600	C21—H21B	0.9600
O2—C7	1.367 (4)	C21—H21C	0.9600
O2—C8	1.410 (4)	C22—C27	1.379 (5)
N2—C40	1.314 (4)	C22—C23	1.392 (5)
N2—C41	1.363 (4)	C23—C24	1.378 (5)
C2—C3	1.365 (4)	C23—H23A	0.9300
C2—C7	1.404 (4)	C24—C25	1.377 (5)
O3—C10	1.280 (3)	C24—C29	1.523 (4)
O3—Tm1ⁱ	2.2840 (18)	C25—C26	1.388 (5)
C3—C4	1.390 (4)	C25—H25A	0.9300
C3—H3A	0.9300	C26—C27	1.383 (5)
O4—C10	1.240 (4)	C26—H26A	0.9300
C4—C5	1.375 (4)	C28—H28A	0.9600
C4—H4A	0.9300	C28—H28B	0.9600
O5—C12	1.374 (4)	C28—H28C	0.9600
O5—C11	1.403 (5)	C29—C30	1.517 (4)
C5—C6	1.387 (4)	C29—H29A	0.9700
C5—C9	1.511 (4)	C29—H29B	0.9700
C6—C7	1.376 (4)	C31—C32	1.398 (4)
C6—H6A	0.9300	C31—H31A	0.9300
O6—C17	1.362 (4)	C32—C33	1.361 (5)
O6—C18	1.425 (5)	C32—H32A	0.9300
O7—C20	1.242 (4)	C33—C34	1.378 (5)
O8—C20	1.264 (4)	C33—H33A	0.9300
C8—H8A	0.9600	C34—C42	1.418 (4)
C8—H8B	0.9600	C34—C35	1.436 (5)
C8—H8C	0.9600	C35—C36	1.333 (6)
C9—C10	1.500 (5)	C35—H35A	0.9300
C9—H9A	0.9700	C36—C37	1.430 (6)
C9—H9B	0.9700	C36—H36A	0.9300
O9—C22	1.380 (4)	C37—C38	1.388 (6)
O9—C21	1.381 (5)	C37—C41	1.414 (4)
O10—C27	1.367 (4)	C38—C39	1.356 (6)
O10—C28	1.415 (5)	C38—H38A	0.9300
O11—C30	1.259 (4)	C39—C40	1.404 (5)
C11—H11C	0.9600	C39—H39A	0.9300
C11—H11D	0.9600	C40—H40A	0.9300
C11—H11A	0.9600	C41—C42	1.419 (5)
C12—C13	1.359 (5)

O3ⁱ—Tm1—O12ⁱ	75.69 (7)	O3—C10—Tm1	61.27 (16)
O3ⁱ—Tm1—O11	76.05 (7)	C9—C10—Tm1	178.2 (2)
O12ⁱ—Tm1—O11	138.51 (8)	C27—O10—C28	117.0 (3)
O3ⁱ—Tm1—O8	89.39 (8)	C30—O11—Tm1	135.28 (19)
O12ⁱ—Tm1—O8	79.23 (8)	O5—C11—H11C	109.5
O11—Tm1—O8	129.97 (7)	O5—C11—H11D	109.5
O3ⁱ—Tm1—O7	74.97 (7)	H11C—C11—H11D	109.5
O12ⁱ—Tm1—O7	124.10 (7)	O5—C11—H11A	109.5
O11—Tm1—O7	75.85 (8)	H11C—C11—H11A	109.5
O8—Tm1—O7	54.12 (8)	H11D—C11—H11A	109.5
O3ⁱ—Tm1—O4	124.40 (7)	C13—C12—O5	125.5 (3)
O12ⁱ—Tm1—O4	93.43 (7)	C13—C12—C17	119.9 (3)
O11—Tm1—O4	78.36 (7)	O5—C12—C17	114.6 (3)
O8—Tm1—O4	142.79 (8)	C30—O12—Tm1ⁱ	137.4 (2)
O7—Tm1—O4	142.18 (7)	C12—C13—C14	120.4 (3)
O3ⁱ—Tm1—O3	72.78 (7)	C12—C13—H13A	119.8
O12ⁱ—Tm1—O3	71.47 (8)	C14—C13—H13A	119.8
O11—Tm1—O3	71.52 (7)	C15—C14—C13	120.3 (3)
O8—Tm1—O3	148.56 (7)	C15—C14—H14A	119.9
O7—Tm1—O3	138.45 (7)	C13—C14—H14A	119.9
O4—Tm1—O3	52.42 (6)	C16—C15—C14	118.7 (3)
O3ⁱ—Tm1—N2	141.43 (8)	C16—C15—C19	120.3 (3)
O12ⁱ—Tm1—N2	139.68 (8)	C14—C15—C19	121.0 (3)
O11—Tm1—N2	78.56 (8)	C17—C16—C15	121.5 (3)
O8—Tm1—N2	85.13 (8)	C17—C16—H16A	119.2
O7—Tm1—N2	70.97 (7)	C15—C16—H16A	119.2
O4—Tm1—N2	77.18 (8)	O6—C17—C16	125.2 (3)
O3—Tm1—N2	124.89 (7)	O6—C17—C12	115.6 (3)
O3ⁱ—Tm1—N1	149.64 (8)	C16—C17—C12	119.2 (3)
O12ⁱ—Tm1—N1	75.49 (8)	O6—C18—H18A	109.5
O11—Tm1—N1	133.46 (7)	O6—C18—H18B	109.5
O8—Tm1—N1	76.06 (8)	H18A—C18—H18B	109.5
O7—Tm1—N1	114.57 (8)	O6—C18—H18C	109.5
O4—Tm1—N1	66.81 (8)	H18A—C18—H18C	109.5
O3—Tm1—N1	106.50 (7)	H18B—C18—H18C	109.5
N2—Tm1—N1	64.71 (9)	C15—C19—C20	114.9 (3)
O3ⁱ—Tm1—C20	81.95 (8)	C15—C19—H19A	108.5
O12ⁱ—Tm1—C20	102.70 (9)	C20—C19—H19A	108.5
O11—Tm1—C20	102.70 (9)	C15—C19—H19B	108.5
O8—Tm1—C20	27.28 (9)	C20—C19—H19B	108.5
O7—Tm1—C20	26.86 (8)	H19A—C19—H19B	107.5
O4—Tm1—C20	152.20 (8)	O7—C20—O8	121.0 (3)
O3—Tm1—C20	154.73 (7)	O7—C20—C19	121.7 (3)
N2—Tm1—C20	75.87 (8)	O8—C20—C19	117.3 (3)
N1—Tm1—C20	95.26 (9)	O7—C20—Tm1	62.72 (17)
O3ⁱ—Tm1—C10	99.16 (8)	O8—C20—Tm1	58.36 (17)
O12ⁱ—Tm1—C10	81.72 (8)	C19—C20—Tm1	175.2 (3)
O11—Tm1—C10	73.53 (8)	O9—C21—H21A	109.5
O8—Tm1—C10	156.48 (8)	O9—C21—H21B	109.5
O7—Tm1—C10	149.32 (8)	H21A—C21—H21B	109.5
O4—Tm1—C10	25.70 (7)	O9—C21—H21C	109.5
O3—Tm1—C10	26.72 (7)	H21A—C21—H21C	109.5
N2—Tm1—C10	100.89 (8)	H21B—C21—H21C	109.5
N1—Tm1—C10	85.93 (8)	C27—C22—O9	114.8 (3)
C20—Tm1—C10	175.58 (9)	C27—C22—C23	119.8 (3)
O3ⁱ—Tm1—Tm1ⁱ	38.27 (5)	O9—C22—C23	125.4 (4)
O12ⁱ—Tm1—Tm1ⁱ	69.35 (5)	C24—C23—C22	121.2 (4)
O11—Tm1—Tm1ⁱ	69.60 (5)	C24—C23—H23A	119.4
O8—Tm1—Tm1ⁱ	123.15 (6)	C22—C23—H23A	119.4
O7—Tm1—Tm1ⁱ	109.36 (5)	C25—C24—C23	118.5 (3)
O4—Tm1—Tm1ⁱ	86.54 (5)	C25—C24—C29	120.0 (3)
O3—Tm1—Tm1ⁱ	34.51 (4)	C23—C24—C29	121.5 (3)
N2—Tm1—Tm1ⁱ	146.58 (7)	C24—C25—C26	121.1 (3)
N1—Tm1—Tm1ⁱ	134.10 (6)	C24—C25—H25A	119.4
C20—Tm1—Tm1ⁱ	120.22 (6)	C26—C25—H25A	119.4
C10—Tm1—Tm1ⁱ	61.01 (6)	C27—C26—C25	119.9 (4)
C31—N1—C42	117.6 (3)	C27—C26—H26A	120.0
C31—N1—Tm1	124.5 (2)	C25—C26—H26A	120.0
C42—N1—Tm1	117.2 (2)	O10—C27—C22	116.6 (3)
C2—O1—C1	116.1 (2)	O10—C27—C26	123.9 (4)
O1—C1—H1A	109.5	C22—C27—C26	119.5 (3)
O1—C1—H1B	109.5	O10—C28—H28A	109.5
H1A—C1—H1B	109.5	O10—C28—H28B	109.5
O1—C1—H1C	109.5	H28A—C28—H28B	109.5
H1A—C1—H1C	109.5	O10—C28—H28C	109.5
H1B—C1—H1C	109.5	H28A—C28—H28C	109.5
C7—O2—C8	117.0 (3)	H28B—C28—H28C	109.5
C40—N2—C41	118.4 (3)	C30—C29—C24	110.6 (3)
C40—N2—Tm1	121.5 (2)	C30—C29—H29A	109.5
C41—N2—Tm1	120.0 (2)	C24—C29—H29A	109.5
C3—C2—O1	124.8 (3)	C30—C29—H29B	109.5
C3—C2—C7	118.9 (3)	C24—C29—H29B	109.5
O1—C2—C7	116.4 (3)	H29A—C29—H29B	108.1
C10—O3—Tm1ⁱ	158.6 (2)	O12—C30—O11	125.8 (3)
C10—O3—Tm1	92.01 (18)	O12—C30—C29	116.7 (3)
Tm1ⁱ—O3—Tm1	107.22 (7)	O11—C30—C29	117.4 (3)
C2—C3—C4	120.2 (3)	N1—C31—C32	123.9 (3)
C2—C3—H3A	119.9	N1—C31—H31A	118.0
C4—C3—H3A	119.9	C32—C31—H31A	118.0
C10—O4—Tm1	95.47 (17)	C33—C32—C31	118.4 (4)
C5—C4—C3	121.8 (3)	C33—C32—H32A	120.8
C5—C4—H4A	119.1	C31—C32—H32A	120.8
C3—C4—H4A	119.1	C32—C33—C34	120.3 (3)
C12—O5—C11	117.8 (3)	C32—C33—H33A	119.9
C4—C5—C6	117.4 (3)	C34—C33—H33A	119.9
C4—C5—C9	121.0 (3)	C33—C34—C42	118.1 (3)
C6—C5—C9	121.5 (3)	C33—C34—C35	123.7 (4)
C7—C6—C5	121.7 (3)	C42—C34—C35	118.2 (4)
C7—C6—H6A	119.2	C36—C35—C34	121.5 (4)
C5—C6—H6A	119.2	C36—C35—H35A	119.2
C17—O6—C18	118.0 (3)	C34—C35—H35A	119.2
C20—O7—Tm1	90.42 (18)	C35—C36—C37	121.8 (3)
O2—C7—C6	125.3 (3)	C35—C36—H36A	119.1
O2—C7—C2	114.9 (3)	C37—C36—H36A	119.1
C6—C7—C2	119.8 (3)	C38—C37—C41	118.3 (3)
C20—O8—Tm1	94.4 (2)	C38—C37—C36	123.4 (3)
O2—C8—H8A	109.5	C41—C37—C36	118.3 (4)
O2—C8—H8B	109.5	C39—C38—C37	119.8 (3)
H8A—C8—H8B	109.5	C39—C38—H38A	120.1
O2—C8—H8C	109.5	C37—C38—H38A	120.1
H8A—C8—H8C	109.5	C38—C39—C40	118.9 (4)
H8B—C8—H8C	109.5	C38—C39—H39A	120.6
C10—C9—C5	118.0 (3)	C40—C39—H39A	120.6
C10—C9—H9A	107.8	N2—C40—C39	123.2 (4)
C5—C9—H9A	107.8	N2—C40—H40A	118.4
C10—C9—H9B	107.8	C39—C40—H40A	118.4
C5—C9—H9B	107.8	N2—C41—C37	121.3 (3)
H9A—C9—H9B	107.1	N2—C41—C42	118.6 (3)
C22—O9—C21	118.6 (4)	C37—C41—C42	120.1 (3)
O4—C10—O3	120.1 (3)	N1—C42—C34	121.7 (3)
O4—C10—C9	122.9 (3)	N1—C42—C41	118.4 (3)
O3—C10—C9	117.0 (3)	C34—C42—C41	119.9 (3)
O4—C10—Tm1	58.82 (15)

O3ⁱ—Tm1—N1—C31	25.7 (3)	N2—Tm1—C10—O4	23.0 (2)
O12ⁱ—Tm1—N1—C31	6.9 (2)	N1—Tm1—C10—O4	−40.31 (18)
O11—Tm1—N1—C31	−138.2 (2)	Tm1ⁱ—Tm1—C10—O4	172.9 (2)
O8—Tm1—N1—C31	89.2 (3)	O3ⁱ—Tm1—C10—O3	−9.1 (2)
O7—Tm1—N1—C31	128.1 (2)	O12ⁱ—Tm1—C10—O3	64.85 (16)
O4—Tm1—N1—C31	−93.3 (3)	O11—Tm1—C10—O3	−81.50 (16)
O3—Tm1—N1—C31	−58.3 (3)	O8—Tm1—C10—O3	101.0 (2)
N2—Tm1—N1—C31	−179.6 (3)	O7—Tm1—C10—O3	−85.0 (2)
C20—Tm1—N1—C31	108.7 (3)	O4—Tm1—C10—O3	−178.9 (3)
C10—Tm1—N1—C31	−75.6 (3)	N2—Tm1—C10—O3	−155.98 (16)
Tm1ⁱ—Tm1—N1—C31	−33.8 (3)	N1—Tm1—C10—O3	140.75 (17)
O3ⁱ—Tm1—N1—C42	−163.31 (18)	Tm1ⁱ—Tm1—C10—O3	−6.08 (13)
O12ⁱ—Tm1—N1—C42	178.0 (2)	O3ⁱ—Tm1—O11—C30	−22.7 (3)
O11—Tm1—N1—C42	32.8 (2)	O12ⁱ—Tm1—O11—C30	25.6 (3)
O8—Tm1—N1—C42	−99.8 (2)	O8—Tm1—O11—C30	−99.8 (3)
O7—Tm1—N1—C42	−60.8 (2)	O7—Tm1—O11—C30	−100.4 (3)
O4—Tm1—N1—C42	77.7 (2)	O4—Tm1—O11—C30	107.5 (3)
O3—Tm1—N1—C42	112.7 (2)	O3—Tm1—O11—C30	53.5 (3)
N2—Tm1—N1—C42	−8.6 (2)	N2—Tm1—O11—C30	−173.4 (3)
C20—Tm1—N1—C42	−80.3 (2)	N1—Tm1—O11—C30	149.0 (3)
C10—Tm1—N1—C42	95.5 (2)	C20—Tm1—O11—C30	−100.9 (3)
Tm1ⁱ—Tm1—N1—C42	137.26 (18)	C10—Tm1—O11—C30	81.5 (3)
O3ⁱ—Tm1—N2—C40	−16.0 (3)	Tm1ⁱ—Tm1—O11—C30	16.9 (3)
O12ⁱ—Tm1—N2—C40	−165.9 (2)	C11—O5—C12—C13	−5.0 (6)
O11—Tm1—N2—C40	33.5 (3)	C11—O5—C12—C17	174.0 (4)
O8—Tm1—N2—C40	−98.9 (3)	O5—C12—C13—C14	178.4 (4)
O7—Tm1—N2—C40	−45.3 (3)	C17—C12—C13—C14	−0.7 (6)
O4—Tm1—N2—C40	114.0 (3)	C12—C13—C14—C15	0.1 (6)
O3—Tm1—N2—C40	91.2 (3)	C13—C14—C15—C16	1.0 (6)
N1—Tm1—N2—C40	−175.8 (3)	C13—C14—C15—C19	179.3 (3)
C20—Tm1—N2—C40	−72.9 (3)	C14—C15—C16—C17	−1.6 (5)
C10—Tm1—N2—C40	104.1 (3)	C19—C15—C16—C17	−179.9 (3)
Tm1ⁱ—Tm1—N2—C40	51.3 (3)	C18—O6—C17—C16	−7.7 (6)
O3ⁱ—Tm1—N2—C41	167.8 (2)	C18—O6—C17—C12	172.8 (4)
O12ⁱ—Tm1—N2—C41	17.9 (3)	C15—C16—C17—O6	−178.4 (3)
O11—Tm1—N2—C41	−142.6 (2)	C15—C16—C17—C12	1.1 (5)
O8—Tm1—N2—C41	84.9 (2)	C13—C12—C17—O6	179.7 (3)
O7—Tm1—N2—C41	138.5 (2)	O5—C12—C17—O6	0.5 (5)
O4—Tm1—N2—C41	−62.1 (2)	C13—C12—C17—C16	0.1 (6)
O3—Tm1—N2—C41	−85.0 (2)	O5—C12—C17—C16	−179.1 (3)
N1—Tm1—N2—C41	8.0 (2)	C16—C15—C19—C20	102.8 (4)
C20—Tm1—N2—C41	111.0 (2)	C14—C15—C19—C20	−75.4 (4)
C10—Tm1—N2—C41	−72.1 (2)	Tm1—O7—C20—O8	−3.0 (3)
Tm1ⁱ—Tm1—N2—C41	−124.9 (2)	Tm1—O7—C20—C19	177.8 (3)
C1—O1—C2—C3	−17.4 (4)	Tm1—O8—C20—O7	3.1 (3)
C1—O1—C2—C7	163.7 (3)	Tm1—O8—C20—C19	−177.6 (2)
O3ⁱ—Tm1—O3—C10	170.6 (2)	C15—C19—C20—O8	−171.4 (3)
O12ⁱ—Tm1—O3—C10	−109.14 (17)	O3ⁱ—Tm1—C20—O7	−72.51 (16)
O11—Tm1—O3—C10	89.95 (17)	O12ⁱ—Tm1—C20—O7	−145.79 (16)
O8—Tm1—O3—C10	−131.31 (18)	O11—Tm1—C20—O7	1.14 (17)
O7—Tm1—O3—C10	129.97 (17)	O8—Tm1—C20—O7	−177.0 (3)
O4—Tm1—O3—C10	0.58 (16)	O4—Tm1—C20—O7	90.2 (2)
N2—Tm1—O3—C10	29.2 (2)	O3—Tm1—C20—O7	−72.4 (3)
N1—Tm1—O3—C10	−41.16 (17)	N2—Tm1—C20—O7	75.68 (17)
C20—Tm1—O3—C10	170.5 (2)	N1—Tm1—C20—O7	137.93 (16)
Tm1ⁱ—Tm1—O3—C10	170.6 (2)	Tm1ⁱ—Tm1—C20—O7	−72.47 (17)
O3ⁱ—Tm1—O3—Tm1ⁱ	0.0	O3ⁱ—Tm1—C20—O8	104.51 (17)
O12ⁱ—Tm1—O3—Tm1ⁱ	80.27 (8)	O12ⁱ—Tm1—C20—O8	31.24 (18)
O11—Tm1—O3—Tm1ⁱ	−80.64 (8)	O11—Tm1—C20—O8	178.16 (16)
O8—Tm1—O3—Tm1ⁱ	58.10 (16)	O7—Tm1—C20—O8	177.0 (3)
O7—Tm1—O3—Tm1ⁱ	−40.62 (13)	O4—Tm1—C20—O8	−92.7 (2)
O4—Tm1—O3—Tm1ⁱ	−170.01 (13)	O3—Tm1—C20—O8	104.6 (2)
N2—Tm1—O3—Tm1ⁱ	−141.43 (9)	N2—Tm1—C20—O8	−107.29 (18)
N1—Tm1—O3—Tm1ⁱ	148.25 (9)	N1—Tm1—C20—O8	−45.04 (18)
C20—Tm1—O3—Tm1ⁱ	−0.1 (2)	Tm1ⁱ—Tm1—C20—O8	104.56 (17)
C10—Tm1—O3—Tm1ⁱ	−170.6 (2)	C21—O9—C22—C27	173.0 (4)
O1—C2—C3—C4	178.1 (3)	C21—O9—C22—C23	−7.0 (6)
C7—C2—C3—C4	−3.1 (5)	C27—C22—C23—C24	−0.2 (6)
O3ⁱ—Tm1—O4—C10	−12.2 (2)	O9—C22—C23—C24	179.8 (4)
O12ⁱ—Tm1—O4—C10	62.79 (19)	C22—C23—C24—C25	−0.3 (5)
O11—Tm1—O4—C10	−76.13 (18)	C22—C23—C24—C29	179.9 (3)
O8—Tm1—O4—C10	139.46 (18)	C23—C24—C25—C26	0.1 (5)
O7—Tm1—O4—C10	−123.88 (19)	C29—C24—C25—C26	179.9 (3)
O3—Tm1—O4—C10	−0.60 (16)	C24—C25—C26—C27	0.6 (6)
N2—Tm1—O4—C10	−156.9 (2)	C28—O10—C27—C22	−178.8 (4)
N1—Tm1—O4—C10	135.4 (2)	C28—O10—C27—C26	0.1 (6)
C20—Tm1—O4—C10	−171.3 (2)	O9—C22—C27—O10	−0.2 (5)
Tm1ⁱ—Tm1—O4—C10	−6.26 (18)	C23—C22—C27—O10	179.8 (3)
C2—C3—C4—C5	−1.3 (5)	O9—C22—C27—C26	−179.1 (4)
C3—C4—C5—C6	4.3 (5)	C23—C22—C27—C26	0.9 (6)
C3—C4—C5—C9	−172.3 (3)	C25—C26—C27—O10	−179.9 (4)
C4—C5—C6—C7	−3.0 (5)	C25—C26—C27—C22	−1.1 (6)
C9—C5—C6—C7	173.6 (3)	C25—C24—C29—C30	48.9 (4)
O3ⁱ—Tm1—O7—C20	102.08 (17)	C23—C24—C29—C30	−131.3 (3)
O12ⁱ—Tm1—O7—C20	41.48 (19)	Tm1ⁱ—O12—C30—O11	8.3 (5)
O11—Tm1—O7—C20	−178.85 (17)	Tm1ⁱ—O12—C30—C29	−169.3 (2)
O8—Tm1—O7—C20	1.68 (16)	Tm1—O11—C30—O12	−22.4 (5)
O4—Tm1—O7—C20	−130.47 (17)	Tm1—O11—C30—C29	155.2 (2)
O3—Tm1—O7—C20	142.17 (16)	C24—C29—C30—O12	74.1 (4)
N2—Tm1—O7—C20	−96.29 (18)	C24—C29—C30—O11	−103.7 (3)
N1—Tm1—O7—C20	−47.19 (18)	C42—N1—C31—C32	0.9 (5)
C10—Tm1—O7—C20	−175.35 (16)	Tm1—N1—C31—C32	171.9 (3)
Tm1ⁱ—Tm1—O7—C20	119.15 (16)	N1—C31—C32—C33	−1.5 (6)
C8—O2—C7—C6	−12.4 (5)	C31—C32—C33—C34	0.4 (5)
C8—O2—C7—C2	168.0 (3)	C32—C33—C34—C42	1.0 (5)
C5—C6—C7—O2	179.1 (3)	C32—C33—C34—C35	−179.0 (3)
C5—C6—C7—C2	−1.2 (5)	C33—C34—C35—C36	−177.3 (4)
C3—C2—C7—O2	−176.0 (3)	C42—C34—C35—C36	2.7 (6)
O1—C2—C7—O2	2.9 (4)	C34—C35—C36—C37	−0.4 (6)
C3—C2—C7—C6	4.3 (4)	C35—C36—C37—C38	178.0 (4)
O1—C2—C7—C6	−176.8 (3)	C35—C36—C37—C41	−3.0 (6)
O3ⁱ—Tm1—O8—C20	−73.46 (17)	C41—C37—C38—C39	−0.1 (5)
O12ⁱ—Tm1—O8—C20	−149.01 (18)	C36—C37—C38—C39	178.8 (4)
O11—Tm1—O8—C20	−2.3 (2)	C37—C38—C39—C40	−2.1 (6)
O7—Tm1—O8—C20	−1.66 (16)	C41—N2—C40—C39	0.7 (5)
O4—Tm1—O8—C20	129.61 (17)	Tm1—N2—C40—C39	−175.5 (3)
O3—Tm1—O8—C20	−127.64 (18)	C38—C39—C40—N2	1.9 (6)
N2—Tm1—O8—C20	68.32 (18)	C40—N2—C41—C37	−3.0 (5)
N1—Tm1—O8—C20	133.45 (18)	Tm1—N2—C41—C37	173.2 (2)
C10—Tm1—O8—C20	174.55 (18)	C40—N2—C41—C42	176.6 (3)
Tm1ⁱ—Tm1—O8—C20	−92.58 (17)	Tm1—N2—C41—C42	−7.1 (4)
C4—C5—C9—C10	−128.0 (4)	C38—C37—C41—N2	2.8 (5)
C6—C5—C9—C10	55.6 (5)	C36—C37—C41—N2	−176.2 (3)
Tm1—O4—C10—O3	1.1 (3)	C38—C37—C41—C42	−176.8 (3)
Tm1—O4—C10—C9	−179.4 (3)	C36—C37—C41—C42	4.1 (5)
Tm1ⁱ—O3—C10—O4	153.6 (4)	C31—N1—C42—C34	0.6 (4)
Tm1—O3—C10—O4	−1.1 (3)	Tm1—N1—C42—C34	−171.0 (2)
Tm1ⁱ—O3—C10—C9	−26.0 (7)	C31—N1—C42—C41	−179.5 (3)
Tm1—O3—C10—C9	179.4 (3)	Tm1—N1—C42—C41	8.9 (4)
Tm1ⁱ—O3—C10—Tm1	154.6 (5)	C33—C34—C42—N1	−1.6 (5)
C5—C9—C10—O4	9.4 (5)	C35—C34—C42—N1	178.4 (3)
C5—C9—C10—O3	−171.1 (3)	C33—C34—C42—C41	178.5 (3)
O3ⁱ—Tm1—C10—O4	169.83 (18)	C35—C34—C42—C41	−1.5 (5)
O12ⁱ—Tm1—C10—O4	−116.22 (19)	N2—C41—C42—N1	−1.5 (4)
O11—Tm1—C10—O4	97.43 (18)	C37—C41—C42—N1	178.2 (3)
O8—Tm1—C10—O4	−80.1 (3)	N2—C41—C42—C34	178.4 (3)
O7—Tm1—C10—O4	93.9 (2)	C37—C41—C42—C34	−1.9 (5)
O3—Tm1—C10—O4	178.9 (3)

Symmetry code: (i) −x, −y, −z.

Experimental details

Crystal data
Chemical formula	[Tm₂(C₁₀H₁₁O₄)₆(C₁₂H₈N₂)₂]
M_r	1869.40
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	12.3025 (1), 12.3483 (2), 14.5883 (2)
α, β, γ (°)	91.457 (1), 103.403 (1), 114.406 (1)
V (Å³)	1944.71 (4)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	2.35
Crystal size (mm)	0.35 × 0.11 × 0.10

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.747, 0.798
No. of measured, independent and observed [I > 2σ(I)] reflections	32353, 6861, 5961
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.058, 1.03
No. of reflections	6861
No. of parameters	514
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.64, −0.32

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

References

Bruker (1997). SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (1999). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Fang, R.-Q. & Zhang, X.-M. (2006). Inorg. Chem. 45, 4801–4810. Web of Science CSD CrossRef PubMed CAS Google Scholar
Li, H.-Q., Xian, H.-D., Liu, J.-F. & Zhao, G.-L. (2008). Acta Cryst. E64, m1593–m1594. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, G.-M., Duan, C.-S., Liu, H.-L. & Li, H. (2008). Acta Cryst. E64, m468–m469. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wang, X.-X. & Sevov, S. (2008). Inorg. Chem. 47, 1037–1043. Web of Science CSD CrossRef PubMed CAS Google Scholar
Yao, Y.-L., Che, Y.-X. & Zheng, J.-M. (2008). Cryst. Growth Des. 8, 2299–2306. Web of Science CSD CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.