Poly[diaqua­tris(μ₄-benzene-1,3-di­carboxyl­ato)diterbium(III)]

The title terbium coordination polymer, {[Tb₂(C₈H₄O₄)₃(H₂O)₂]}_n, was obtained by the hydro­thermal reaction of Tb(NO₃)₃ with benzene-1,3-dicarboxylic acid (1,3-BDC) in alkaline aqueous solution. In the asymmetric unit, there are two crystallographically independent Tb^III ions: one seven-coordinate Tb centre is coordinated by six O atoms from six 1,3-BDC ligands and one water mol­ecule, and the other Tb centre is eight-coordinate and surrounded by seven O atoms from six 1,3-BDC ligands and one water mol­ecule. The bridging ligands link the metal centres, forming a three-dimensional network which is further stabilized by hydrogen-bonding inter­actions. One benzene ring is disordered over two positions with site occupancies of 0.60 (3) and 0.40 (3).

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.009 Å
• Disorder in main residue
• R factor = 0.034
• wR factor = 0.073
• Data-to-parameter ratio = 12.6

checkCIF/PLATON results

No syntax errors found





Alert level B
PLAT420_ALERT_2_B D-H Without Acceptor       O2W    -   H4W    ...          ?
PLAT731_ALERT_1_B Bond    Calc     0.83(5), Rep   0.818(10) ......       5.00 su-Ra
              O1W  -H1W     1.555   1.555
PLAT731_ALERT_1_B Bond    Calc     0.81(7), Rep   0.819(10) ......       7.00 su-Ra
              O1W  -H2W     1.555   1.555
PLAT731_ALERT_1_B Bond    Calc     0.83(5), Rep   0.823(10) ......       5.00 su-Ra
              O2W  -H3W     1.555   1.555
PLAT731_ALERT_1_B Bond    Calc     0.83(5), Rep   0.822(10) ......       5.00 su-Ra
              O2W  -H4W     1.555   1.555
PLAT732_ALERT_1_B Angle   Calc      105(8), Rep   104.0(17) ......       4.71 su-Ra
              H1W  -O1W  -H2W     1.555   1.555   1.555
PLAT735_ALERT_1_B D-H     Calc     0.83(5), Rep   0.818(10) ......       5.00 su-Ra
              O1W  -H1W     1.555   1.555
PLAT735_ALERT_1_B D-H     Calc     0.81(7), Rep   0.819(10) ......       7.00 su-Ra
              O1W  -H2W     1.555   1.555
PLAT735_ALERT_1_B D-H     Calc     0.83(5), Rep   0.823(10) ......       5.00 su-Ra
              O2W  -H3W     1.555   1.555

Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.05
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT153_ALERT_1_C The su's on the Cell Axes   are Equal (x 100000)         30 Ang.
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.40 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O5
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Tb1
PLAT301_ALERT_3_C Main Residue  Disorder .........................       9.00 Perc.
PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...         10
PLAT732_ALERT_1_C Angle   Calc      103(5), Rep   103.3(17) ......       2.94 su-Ra
              H3W  -O2W  -H4W     1.555   1.555   1.555
PLAT736_ALERT_1_C H...A   Calc     1.95(5), Rep   1.959(14) ......       3.57 su-Ra
              H3W  -O2      1.555   3.755
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.14 Ratio

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         66

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

  12 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

As a building block, benzene-1,3-dicarboxylic acid (1,3-BDC) is an excellent candidate for the construction of supramolecular complexes (De Bettencourt-Dias, 2005; Zhang et al., 2003). Recently, we obtained the title coordination polymer by the reaction of Tb(NO₃)₃ with benzene-1,3-dicarboxylic acid in alkaline aqueous solution, and its crystal structure is reported here.

In the asymmetric unit of the title complex, there are two crystallographically independent Tb^III ions: one seven-coordinate Tb centre is coordinated by six oxygen atoms from six 1,3-BDC ligands and one water molecule, and the other Tb centre is eight-coordinate and surrounded by seven oxygen atoms from six 1,3-BDC ligands and one water molecules (Fig. 1). The adjacent Tb···Tb separations are 4.690 (4) and 4.698 (5) Å, respectively. The carboxylate groups of 1,3-BDC ligands are distinct, one of which acts as bis(monodentate) bridge, the other acts as chelate and monodentate bridge. They cross-link the metal ions to form a three-dimensional network (Fig. 2). The crystal structure is stabilized by intra/intermolecular O—H···O and C—H···.O hydrogen bonding interactions (Table 1).

Related literature

De Bettencourt-Dias (2005) and Zhang et al. (2003) have described the use of benzene-1,3-dicarboxylic acid (1,3-BDC) in the construction of supramolecular complexes.

S2. Experimental

A mixture of Tb(NO₃)₃ (0.5 mmol, 0.172 g), benzenedicarboxylic acid (0.75 mmol, 0.125 g), NaOH (1.5 mmol; 0.06 g) and H₂O (12 ml) was placed in a 23 ml Teflon reactor, which was heated to 433 K for three days and then cooled to room temperature at a rate of 10 K h^-1. The crystals obtained were washed with water and dryed in air.

S3. Refinement

One of the phenyl rings was found to be split into two positions and the occupancy ratio refined to 0.60 (3) to 0.40 (3). Due to the significant overlap of the disordered atoms the following restraints were applied: The phenyl ring C10 C11 C12 C13 C14 C15 and its disordered counterpart were each restrained to be flat and their equivalent bond distances were restrained to be the same within a standard deviation of 0.01 Å. All water H atoms were tentatively located in difference density Fourier maps and were refined with O–H distance restraints of 0.82 (1) Å and with U_iso(H) = 1.5 U_eq(O). Carbon-bound H atoms were placed at calculated positions and were treated as riding on the parent C atoms with C—H = 0.93 Å, and with U_iso(H) = 1.2 U_eq(C).

Computing details

Data collection: APEX-II (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-XP (Bruker, 2004); software used to prepare material for publication: SHELXTL (Bruker, 2004).

Figures

	Fig. 1. The molecular structure showing the atomic-numbering scheme and displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. The molecular packing showing the intermolecular hydrogen bonding interactions as broken lines. The minor moieties of the disordered phenyl rings were omitted for clarity.

Poly[diaquatris(m₄-benzene-1,3-dicarboxylato)diterbium(III)]

Crystal data

[Tb2(C8H4O4)3(H2O)2]	F(000) = 1608
Mr = 846.21	Dx = 2.245 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4289 reflections
a = 13.2647 (3) Å	θ = 1.7–28.0°
b = 14.3741 (3) Å	µ = 5.68 mm^−1
c = 13.5323 (3) Å	T = 296 K
β = 103.944 (1)°	Block, colorless
V = 2504.14 (9) Å^3	0.15 × 0.14 × 0.11 mm
Z = 4

Data collection

Bruker APEX-II area-detector diffractometer	5182 independent reflections
Radiation source: fine-focus sealed tube	3834 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.077
ϕ and ω scan	θmax = 26.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→16
Tmin = 0.445, Tmax = 0.538	k = −17→18
35926 measured reflections	l = −16→16

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.073	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0245P)^2 + 8.8675P] where P = (Fo^2 + 2Fc^2)/3
5182 reflections	(Δ/σ)max = 0.001
410 parameters	Δρmax = 2.21 e Å^−3
66 restraints	Δρmin = −1.08 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of 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)
C1	0.8731 (5)	0.1394 (4)	0.1428 (4)	0.0231 (14)
C2	0.9120 (5)	0.2379 (4)	0.1428 (5)	0.0273 (15)
C3	0.8840 (5)	0.3000 (4)	0.2099 (5)	0.0292 (15)
H3	0.8430	0.2801	0.2528	0.035*
C4	0.9166 (5)	0.3912 (4)	0.2132 (5)	0.0285 (15)
C5	0.9762 (6)	0.4214 (5)	0.1484 (6)	0.0418 (19)
H5	0.9974	0.4832	0.1498	0.050*
C6	1.0044 (7)	0.3588 (5)	0.0808 (6)	0.051 (2)
H6	1.0443	0.3788	0.0370	0.061*
C7	0.9728 (6)	0.2667 (5)	0.0792 (6)	0.0382 (18)
H7	0.9925	0.2245	0.0353	0.046*
C8	0.8853 (5)	0.4571 (4)	0.2847 (5)	0.0272 (15)
C9	0.6369 (6)	0.4092 (5)	0.1246 (5)	0.0339 (17)
C10	0.6583 (6)	0.4838 (5)	0.0566 (5)	0.0377 (18)
C11	0.6834 (13)	0.5728 (7)	0.0950 (9)	0.021 (7)	0.40 (3)
H11	0.6739	0.5890	0.1587	0.025*	0.40 (3)
C13	0.738 (2)	0.6150 (13)	−0.0580 (11)	0.026 (5)	0.40 (3)
H13	0.7678	0.6582	−0.0932	0.032*	0.40 (3)
C14	0.708 (3)	0.5288 (13)	−0.1007 (15)	0.041 (6)	0.40 (3)
H14	0.7083	0.5155	−0.1677	0.049*	0.40 (3)
C15	0.677 (2)	0.4638 (14)	−0.0398 (12)	0.039 (6)	0.40 (3)
H15	0.6670	0.4029	−0.0634	0.047*	0.40 (3)
C11'	0.7033 (11)	0.5661 (6)	0.1000 (7)	0.022 (4)	0.60 (3)
H11'	0.7203	0.5736	0.1703	0.026*	0.60 (3)
C13'	0.6938 (16)	0.6260 (9)	−0.0677 (7)	0.033 (4)	0.60 (3)
H13'	0.7037	0.6746	−0.1097	0.040*	0.60 (3)
C14'	0.6506 (17)	0.5431 (9)	−0.1100 (10)	0.039 (4)	0.60 (3)
H14'	0.6362	0.5353	−0.1802	0.047*	0.60 (3)
C15'	0.6286 (15)	0.4723 (9)	−0.0504 (7)	0.033 (4)	0.60 (3)
H15'	0.5952	0.4185	−0.0795	0.040*	0.60 (3)
C12	0.7224 (5)	0.6369 (4)	0.0379 (5)	0.0312 (16)
C16	0.7631 (5)	0.7280 (4)	0.0848 (5)	0.0226 (14)
C17	0.6837 (5)	0.0910 (4)	−0.0429 (4)	0.0225 (14)
C18	0.7180 (5)	0.1586 (4)	−0.1142 (5)	0.0258 (15)
C19	0.6553 (6)	0.2320 (5)	−0.1574 (5)	0.0332 (16)
H19	0.5897	0.2385	−0.1450	0.040*
C20	0.6886 (6)	0.2954 (5)	−0.2183 (5)	0.0378 (18)
H20	0.6445	0.3427	−0.2497	0.045*
C21	0.7881 (5)	0.2886 (5)	−0.2329 (5)	0.0341 (17)
H21	0.8119	0.3332	−0.2716	0.041*
C22	0.8525 (5)	0.2159 (4)	−0.1901 (5)	0.0270 (15)
C23	0.8166 (5)	0.1504 (5)	−0.1316 (4)	0.0256 (15)
H23	0.8589	0.1006	−0.1038	0.031*
C24	0.9607 (5)	0.2067 (5)	−0.2044 (5)	0.0279 (15)
O1	0.7873 (3)	0.1236 (3)	0.1631 (3)	0.0279 (10)
O2	0.9288 (4)	0.0743 (3)	0.1211 (4)	0.0335 (11)
O3	0.9080 (4)	0.5415 (3)	0.2778 (4)	0.0390 (12)
O4	0.8359 (4)	0.4262 (3)	0.3473 (4)	0.0364 (12)
O5	0.6263 (4)	0.3265 (3)	0.0916 (4)	0.0436 (13)
O6	0.6325 (4)	0.4317 (3)	0.2125 (4)	0.0423 (13)
O7	0.7630 (3)	0.7967 (3)	0.0277 (3)	0.0290 (11)
O8	0.7966 (4)	0.7328 (3)	0.1800 (3)	0.0311 (11)
O9	0.6139 (3)	0.1186 (3)	−0.0012 (3)	0.0301 (11)
O10	0.7277 (3)	0.0131 (3)	−0.0287 (3)	0.0275 (10)
O11	1.0184 (4)	0.1465 (3)	−0.1523 (3)	0.0329 (11)
O12	0.9859 (4)	0.2601 (3)	−0.2675 (4)	0.0360 (12)
O1W	0.4451 (4)	0.1564 (5)	0.0500 (4)	0.0564 (17)
H1W	0.387 (3)	0.178 (6)	0.048 (6)	0.085*
H2W	0.436 (6)	0.121 (5)	0.002 (5)	0.085*
O2W	0.8967 (4)	−0.0717 (4)	−0.0413 (4)	0.0432 (13)
H3W	0.948 (3)	−0.075 (6)	−0.066 (5)	0.065*
H4W	0.849 (3)	−0.059 (6)	−0.091 (3)	0.065*
Tb1	0.61128 (2)	0.18274 (2)	0.15619 (2)	0.02036 (8)
Tb2	0.82716 (2)	−0.06625 (2)	0.11562 (2)	0.02429 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.022 (4)	0.025 (3)	0.022 (3)	0.002 (3)	0.004 (3)	−0.006 (3)
C2	0.026 (4)	0.023 (4)	0.035 (4)	−0.004 (3)	0.011 (3)	−0.002 (3)
C3	0.029 (4)	0.025 (4)	0.036 (4)	−0.004 (3)	0.013 (3)	−0.010 (3)
C4	0.027 (4)	0.021 (3)	0.041 (4)	0.001 (3)	0.016 (3)	−0.004 (3)
C5	0.058 (5)	0.017 (4)	0.058 (5)	−0.009 (4)	0.031 (4)	−0.006 (3)
C6	0.066 (6)	0.034 (5)	0.069 (6)	−0.012 (4)	0.051 (5)	−0.008 (4)
C7	0.046 (5)	0.029 (4)	0.048 (4)	−0.001 (3)	0.028 (4)	−0.008 (3)
C8	0.021 (4)	0.024 (4)	0.039 (4)	0.000 (3)	0.012 (3)	−0.007 (3)
C9	0.039 (5)	0.030 (4)	0.031 (4)	−0.005 (3)	0.003 (3)	0.008 (3)
C10	0.053 (5)	0.024 (4)	0.034 (4)	−0.010 (3)	0.007 (4)	0.005 (3)
C11	0.013 (8)	0.018 (9)	0.026 (10)	0.006 (7)	−0.006 (6)	−0.001 (7)
C13	0.028 (10)	0.020 (8)	0.031 (8)	0.002 (7)	0.008 (7)	−0.002 (6)
C14	0.055 (11)	0.040 (9)	0.030 (8)	0.003 (8)	0.016 (8)	−0.009 (7)
C15	0.040 (11)	0.033 (9)	0.046 (9)	−0.007 (8)	0.012 (7)	−0.006 (7)
C11'	0.028 (7)	0.019 (7)	0.019 (6)	0.001 (5)	0.006 (5)	0.004 (5)
C13'	0.039 (8)	0.025 (6)	0.032 (6)	−0.001 (6)	0.001 (5)	0.004 (5)
C14'	0.050 (9)	0.033 (7)	0.032 (6)	−0.005 (6)	0.006 (6)	0.001 (5)
C15'	0.034 (8)	0.027 (6)	0.038 (6)	−0.009 (6)	0.006 (5)	−0.003 (5)
C12	0.042 (4)	0.022 (4)	0.029 (4)	−0.004 (3)	0.007 (3)	0.001 (3)
C16	0.016 (3)	0.024 (4)	0.028 (3)	−0.002 (3)	0.005 (3)	−0.002 (3)
C17	0.015 (3)	0.030 (4)	0.022 (3)	−0.003 (3)	0.003 (3)	−0.001 (3)
C18	0.024 (4)	0.026 (4)	0.030 (3)	−0.003 (3)	0.012 (3)	−0.002 (3)
C19	0.024 (4)	0.038 (4)	0.038 (4)	0.007 (3)	0.010 (3)	0.001 (3)
C20	0.031 (4)	0.034 (4)	0.049 (4)	0.011 (3)	0.010 (3)	0.010 (3)
C21	0.032 (4)	0.030 (4)	0.042 (4)	0.006 (3)	0.014 (3)	0.007 (3)
C22	0.026 (4)	0.025 (4)	0.032 (4)	0.005 (3)	0.013 (3)	0.003 (3)
C23	0.025 (4)	0.031 (4)	0.023 (3)	0.000 (3)	0.009 (3)	0.002 (3)
C24	0.027 (4)	0.030 (4)	0.028 (3)	0.004 (3)	0.009 (3)	0.007 (3)
O1	0.021 (3)	0.031 (3)	0.033 (3)	−0.006 (2)	0.010 (2)	−0.006 (2)
O2	0.029 (3)	0.022 (3)	0.052 (3)	−0.002 (2)	0.015 (2)	−0.009 (2)
O3	0.051 (3)	0.021 (3)	0.050 (3)	−0.003 (2)	0.023 (3)	−0.009 (2)
O4	0.040 (3)	0.026 (3)	0.049 (3)	−0.004 (2)	0.023 (2)	−0.009 (2)
O5	0.063 (4)	0.020 (3)	0.048 (3)	−0.010 (2)	0.014 (3)	0.005 (2)
O6	0.063 (4)	0.028 (3)	0.036 (3)	−0.016 (3)	0.011 (2)	0.006 (2)
O7	0.036 (3)	0.017 (2)	0.033 (2)	−0.004 (2)	0.008 (2)	0.0023 (19)
O8	0.030 (3)	0.035 (3)	0.028 (2)	−0.004 (2)	0.008 (2)	−0.004 (2)
O9	0.028 (3)	0.037 (3)	0.029 (2)	0.002 (2)	0.013 (2)	−0.001 (2)
O10	0.029 (3)	0.025 (3)	0.034 (3)	0.004 (2)	0.017 (2)	0.003 (2)
O11	0.028 (3)	0.034 (3)	0.041 (3)	0.002 (2)	0.018 (2)	0.009 (2)
O12	0.029 (3)	0.041 (3)	0.043 (3)	0.003 (2)	0.019 (2)	0.016 (2)
O1W	0.023 (3)	0.088 (5)	0.055 (4)	0.007 (3)	0.003 (3)	−0.038 (3)
O2W	0.043 (3)	0.049 (3)	0.045 (3)	0.006 (3)	0.025 (2)	0.003 (3)
Tb1	0.02051 (17)	0.01598 (16)	0.02636 (16)	−0.00013 (13)	0.00914 (12)	−0.00032 (12)
Tb2	0.02325 (18)	0.01728 (16)	0.03264 (18)	−0.00032 (13)	0.00735 (13)	0.00021 (13)

Geometric parameters (Å, º)

C1—O1	1.255 (7)	C17—O10	1.256 (7)
C1—O2	1.269 (7)	C17—O9	1.259 (7)
C1—C2	1.507 (9)	C17—C18	1.515 (8)
C2—C7	1.377 (9)	C18—C19	1.383 (9)
C2—C3	1.387 (9)	C18—C23	1.388 (9)
C3—C4	1.378 (9)	C19—C20	1.371 (10)
C3—H3	0.9300	C19—H19	0.9300
C4—C5	1.385 (9)	C20—C21	1.384 (10)
C4—C8	1.483 (9)	C20—H20	0.9300
C5—C6	1.397 (10)	C21—C22	1.385 (9)
C5—H5	0.9300	C21—H21	0.9300
C6—C7	1.388 (10)	C22—C23	1.386 (9)
C6—H6	0.9300	C22—C24	1.500 (9)
C7—H7	0.9300	C23—H23	0.9300
C8—O3	1.259 (7)	C24—O12	1.251 (7)
C8—O4	1.269 (8)	C24—O11	1.254 (7)
C9—O6	1.248 (8)	O1—Tb1	2.465 (4)
C9—O5	1.265 (8)	O1—Tb2	2.882 (4)
C9—C10	1.484 (9)	O2—Tb2	2.420 (4)
C10—C11'	1.390 (10)	O3—Tb1^i	2.258 (4)
C10—C11	1.390 (11)	O4—Tb2^i	2.338 (5)
C10—C15	1.413 (13)	O5—Tb1	2.271 (4)
C10—C15'	1.417 (11)	O6—Tb2^i	2.258 (5)
C11—C12	1.382 (11)	O7—Tb2^ii	2.352 (4)
C11—H11	0.9300	O8—Tb1^i	2.370 (4)
C13—C14	1.384 (13)	O9—Tb1	2.329 (4)
C13—C12	1.396 (12)	O10—Tb2	2.369 (4)
C13—H13	0.9300	O11—Tb2^iii	2.299 (5)
C14—C15	1.372 (14)	O12—Tb1^iv	2.310 (4)
C14—H14	0.9300	O1W—Tb1	2.354 (5)
C15—H15	0.9300	O1W—H1W	0.818 (10)
C11'—C12	1.381 (10)	O1W—H2W	0.819 (10)
C11'—H11'	0.9300	O2W—Tb2	2.513 (5)
C13'—C14'	1.385 (12)	O2W—H3W	0.823 (10)
C13'—C12	1.395 (11)	O2W—H4W	0.822 (10)
C13'—H13'	0.9300	Tb1—O3^v	2.258 (4)
C14'—C15'	1.373 (13)	Tb1—O12^vi	2.310 (4)
C14'—H14'	0.9300	Tb1—O8^v	2.370 (4)
C15'—H15'	0.9300	Tb2—O6^v	2.258 (5)
C12—C16	1.499 (9)	Tb2—O11^iii	2.299 (5)
C16—O7	1.253 (7)	Tb2—O4^v	2.338 (5)
C16—O8	1.260 (7)	Tb2—O7^vii	2.352 (4)
O1—C1—O2	121.8 (6)	C20—C21—C22	120.4 (7)
O1—C1—C2	119.9 (6)	C20—C21—H21	119.8
O2—C1—C2	118.3 (6)	C22—C21—H21	119.8
C7—C2—C3	120.4 (6)	C21—C22—C23	119.4 (6)
C7—C2—C1	122.3 (6)	C21—C22—C24	121.6 (6)
C3—C2—C1	117.3 (6)	C23—C22—C24	119.0 (6)
C4—C3—C2	120.1 (6)	C22—C23—C18	120.4 (6)
C4—C3—H3	119.9	C22—C23—H23	119.8
C2—C3—H3	119.9	C18—C23—H23	119.8
C3—C4—C5	120.0 (6)	O12—C24—O11	125.5 (6)
C3—C4—C8	119.5 (6)	O12—C24—C22	117.1 (6)
C5—C4—C8	120.4 (6)	O11—C24—C22	117.4 (6)
C4—C5—C6	119.8 (6)	C1—O1—Tb1	146.1 (4)
C4—C5—H5	120.1	C1—O1—Tb2	84.1 (4)
C6—C5—H5	120.1	Tb1—O1—Tb2	122.75 (16)
C7—C6—C5	119.8 (7)	C1—O2—Tb2	105.8 (4)
C7—C6—H6	120.1	C8—O3—Tb1^i	141.7 (5)
C5—C6—H6	120.1	C8—O4—Tb2^i	141.2 (4)
C2—C7—C6	119.8 (7)	C9—O5—Tb1	137.0 (5)
C2—C7—H7	120.1	C9—O6—Tb2^i	158.7 (5)
C6—C7—H7	120.1	C16—O7—Tb2^ii	113.7 (4)
O3—C8—O4	123.9 (6)	C16—O8—Tb1^i	156.2 (4)
O3—C8—C4	117.2 (6)	C17—O9—Tb1	135.2 (4)
O4—C8—C4	118.9 (6)	C17—O10—Tb2	134.5 (4)
O6—C9—O5	123.6 (6)	C24—O11—Tb2^iii	149.2 (4)
O6—C9—C10	117.6 (6)	C24—O12—Tb1^iv	149.6 (4)
O5—C9—C10	118.8 (6)	Tb1—O1W—H1W	134 (5)
C11'—C10—C15	114.3 (11)	Tb1—O1W—H2W	122 (5)
C11—C10—C15	117.0 (11)	H1W—O1W—H2W	104.0 (17)
C11'—C10—C15'	121.1 (8)	Tb2—O2W—H3W	148 (5)
C11—C10—C15'	118.2 (8)	Tb2—O2W—H4W	108 (5)
C11'—C10—C9	118.7 (7)	H3W—O2W—H4W	103.3 (17)
C11—C10—C9	119.9 (7)	O3^v—Tb1—O5	178.18 (19)
C15—C10—C9	121.7 (10)	O3^v—Tb1—O12^vi	88.87 (17)
C15'—C10—C9	120.1 (7)	O5—Tb1—O12^vi	89.33 (18)
C12—C11—C10	119.5 (9)	O3^v—Tb1—O9	91.95 (17)
C12—C11—H11	120.3	O5—Tb1—O9	89.20 (17)
C10—C11—H11	120.3	O12^vi—Tb1—O9	136.12 (16)
C14—C13—C12	119.9 (15)	O3^v—Tb1—O1W	85.3 (2)
C14—C13—H13	120.1	O5—Tb1—O1W	93.9 (2)
C12—C13—H13	120.1	O12^vi—Tb1—O1W	70.16 (17)
C15—C14—C13	117.2 (18)	O9—Tb1—O1W	66.20 (17)
C15—C14—H14	121.4	O3^v—Tb1—O8^v	89.16 (16)
C13—C14—H14	121.4	O5—Tb1—O8^v	90.58 (16)
C14—C15—C10	124.0 (17)	O12^vi—Tb1—O8^v	74.82 (16)
C14—C15—H15	118.0	O9—Tb1—O8^v	149.05 (16)
C10—C15—H15	118.0	O1W—Tb1—O8^v	144.62 (18)
C12—C11'—C10	119.6 (8)	O3^v—Tb1—O1	82.62 (16)
C12—C11'—H11'	120.2	O5—Tb1—O1	99.09 (17)
C10—C11'—H11'	120.2	O12^vi—Tb1—O1	152.00 (15)
C14'—C13'—C12	120.2 (11)	O9—Tb1—O1	71.07 (15)
C14'—C13'—H13'	119.9	O1W—Tb1—O1	135.00 (16)
C12—C13'—H13'	119.9	O8^v—Tb1—O1	78.42 (15)
C15'—C14'—C13'	121.4 (12)	O6^v—Tb2—O11^iii	78.07 (17)
C15'—C14'—H14'	119.3	O6^v—Tb2—O4^v	77.30 (18)
C13'—C14'—H14'	119.3	O11^iii—Tb2—O4^v	138.85 (15)
C14'—C15'—C10	117.9 (11)	O6^v—Tb2—O7^vii	118.50 (16)
C14'—C15'—H15'	121.1	O11^iii—Tb2—O7^vii	83.35 (16)
C10—C15'—H15'	121.1	O4^v—Tb2—O7^vii	80.15 (16)
C11'—C12—C13'	119.7 (8)	O6^v—Tb2—O10	143.33 (16)
C11—C12—C13'	116.9 (8)	O11^iii—Tb2—O10	135.23 (15)
C11'—C12—C13	119.2 (10)	O4^v—Tb2—O10	80.73 (15)
C11—C12—C13	121.8 (10)	O7^vii—Tb2—O10	85.66 (15)
C11'—C12—C16	119.1 (6)	O6^v—Tb2—O2	89.27 (17)
C11—C12—C16	119.4 (7)	O11^iii—Tb2—O2	87.20 (15)
C13'—C12—C16	120.9 (7)	O4^v—Tb2—O2	124.72 (16)
C13—C12—C16	118.3 (9)	O7^vii—Tb2—O2	147.76 (15)
O7—C16—O8	122.3 (6)	O10—Tb2—O2	79.58 (15)
O7—C16—C12	118.7 (5)	O6^v—Tb2—O2W	145.73 (19)
O8—C16—C12	118.9 (6)	O11^iii—Tb2—O2W	71.18 (17)
O10—C17—O9	125.3 (6)	O4^v—Tb2—O2W	136.65 (17)
O10—C17—C18	118.0 (6)	O7^vii—Tb2—O2W	73.04 (17)
O9—C17—C18	116.7 (6)	O10—Tb2—O2W	64.10 (16)
C19—C18—C23	119.2 (6)	O2—Tb2—O2W	74.73 (17)
C19—C18—C17	121.1 (6)	O6^v—Tb2—O1	78.07 (14)
C23—C18—C17	119.6 (6)	O11^iii—Tb2—O1	128.96 (14)
C20—C19—C18	120.9 (7)	O4^v—Tb2—O1	76.53 (14)
C20—C19—H19	119.6	O7^vii—Tb2—O1	147.41 (14)
C18—C19—H19	119.6	O10—Tb2—O1	68.43 (13)
C19—C20—C21	119.7 (7)	O2—Tb2—O1	48.19 (14)
C19—C20—H20	120.2	O2W—Tb2—O1	110.02 (16)
C21—C20—H20	120.2

Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) x, y+1, z; (iii) −x+2, −y, −z; (iv) x+1/2, −y+1/2, z−1/2; (v) −x+3/2, y−1/2, −z+1/2; (vi) x−1/2, −y+1/2, z+1/2; (vii) x, y−1, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O7^viii	0.82 (1)	2.04 (4)	2.789 (7)	151 (7)
O1W—H2W···O4^ix	0.82 (1)	2.29 (4)	3.020 (7)	149 (7)
O2W—H3W···O2^iii	0.82 (1)	1.96 (1)	2.780 (7)	176 (9)
C3—H3···O8^v	0.93	2.35	3.257 (8)	164
C11′—H11′···O1^i	0.93	2.39	3.284 (10)	161

Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (iii) −x+2, −y, −z; (v) −x+3/2, y−1/2, −z+1/2; (viii) −x+1, −y+1, −z; (ix) x−1/2, −y+1/2, z−1/2.