catena-Poly[[[diaqua­terbium(III)]-tri-μ₂-isonicotinato-κ⁶O:O′] tris(perchlorate) monohydrate]

In the title complex, {[Tb(C₆H₅NO₂)₃(H₂O)₂](ClO₄)₃·H₂O}_n, the Tb^III ion is coordinated by six O atoms from six isonicotinate (inic) ligands and two water mol­ecules, displaying a bicapped trigonal-prismatic geometry. The inic ligands, which are protonated at the pyridine N atom, link the metal centres, forming a polymeric chain running parallel to the a axis. The chains are further assembled via intra- and inter­molecular O—H...O and N—H...O hydrogen-bonding inter­actions into a three-dimensional supra­molecular network involving the inic ligands, the water mol­ecules and the perchlorate anions. One of the perchlorate ions is disordered over two sites with occupancies of 0.561 (17) and 0.439 (17).

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in solvent or counterion
• R factor = 0.021
• wR factor = 0.049
• Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.70 Ratio
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Tb1    --  O2W     ..       7.69 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Tb1    --  O3W     ..       8.58 su
PLAT432_ALERT_2_C Short Inter X...Y Contact  O3     ..  C11     ..       3.00 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O12    ..  C11     ..       2.93 Ang.
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        200 Deg.
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        Cl3
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for       Cl3'
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        Cl1
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        Cl2
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.12 Ratio

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         77
PLAT302_ALERT_4_G Anion/Solvent Disorder .........................      24.00 Perc.

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 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
   6 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

S1. Comment

The design, synthesis, characterization, and properties of supramolecular networks formed by using functionalized organic molecules as bridges between metal centres are of great interest (Rizk et al., 2005; Eddaoudi et al., 2001). As a building block, isonicotinic acid is an excellent candidate for the construction of supramolecular complexes. Recently, we obtained the title new coordination polymer, whise structure is reported here.

In the title compound, each Tb^III centre is coordinated by six oxygen donors of six inic ligands and two water molecules (Fig. 1), and exhibits a bicapped trigonal prismatic coordination geometry. The Tb^III ions are linked by inic ligands to form a polymeric chain in the a axis direction. The Tb···Tb separations between adjacent metal atoms are 4.318 (4) and 5.259 (5) Å. Intra- and intermolecular O—H···O and N—H···O hydrogen bonding interaction (Table 1) involving the inic ligands, the water molecules and the perchlorate ions assemble neighboring chains into a three-dimensional supramolecular network (Fig. 2).

Related literature

For related literature, see: Eddaoudi et al. (2001); Rizk et al. (2005).

S2. Experimental

A mixture of Tb₄O₇ (0.189 g, 0.25 mmol), isonicotinic acid (0.135 g, 1.5 mmol) and water (10 ml) in the presence of HClO₄ (0.385 mmol) was stirred vigorously for 20 min and then sealed into a Teflon-lined stainless-steel autoclave (20 ml capacity). The autoclave was heated to and maintained at 433 K for 3 days, and then cooled to room temperature at 5 K h^-1 to obtain colourless block-shaped crystals of the title compound suitable for X-ray analysis.

S3. Refinement

The disordered perchlorate ion was spli into two components with site occupancy factors of 0.561 (17) and0.439 (17). The Cl···O and O···O distances were restrained to be 1.44 (1) and 2.35 (1) Å, respectively. Water H atoms were tentatively located in difference Fourier maps and were refined with distance restraints of O–H = 0.84 Å and H···H = 1.35 Å, and with U_iso(H) = 1.5 U_eq(O). All other H atoms were placed at calculated positions and were treated as riding with C—H = 0.93 Å, N—H = 0.86 Å, and with U_iso(H) = 1.2 U_eq(C, N).

Computing details

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures

	Fig. 1. The molecular structure of the title compound showing the atomic-numbering scheme. Displacement ellipsoids drawn at the 30% probability level. Only the major component of disorder is shown. [Symmetry codes: (i) 1-x, 1-y, 1-z; (ii) -x, 1-y, 1-z].
	Fig. 2. The supramolecular network of the title compound viewed along the a axis. Only the major componentof disorder is shown.

catena-Poly[[[diaquaterbium(III)]-tri-µ₂-isonicotinato- κ⁶O:O'] tris(perchlorate) monohydrate]

Crystal data

[Tb(C6H5NO2)3(H2O)2](ClO4)3·H2O	Z = 2
Mr = 880.65	F(000) = 868
Triclinic, P1	Dx = 2.068 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.5270 (4) Å	Cell parameters from 6377 reflections
b = 10.9508 (4) Å	θ = 1.7–28.0°
c = 15.1309 (6) Å	µ = 2.88 mm^−1
α = 104.402 (2)°	T = 296 K
β = 91.480 (2)°	Block, colourless
γ = 111.159 (2)°	0.20 × 0.18 × 0.15 mm
V = 1414.17 (10) Å^3

Data collection

Bruker APEXII area-detector diffractometer	6605 independent reflections
Radiation source: fine-focus sealed tube	6206 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
ϕ and ω scan	θmax = 27.8°, θmin = 2.1°
Absorption correction: multi-scan (SADABS, Sheldrick, 1996)	h = −12→12
Tmin = 0.566, Tmax = 0.646	k = −14→14
19700 measured reflections	l = −19→19

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)] = 0.021	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.048	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.021P)^2 + 1.1255P] where P = (Fo^2 + 2Fc^2)/3
6605 reflections	(Δ/σ)max = 0.001
452 parameters	Δρmax = 0.95 e Å^−3
77 restraints	Δρmin = −0.79 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	0.5075 (3)	0.5494 (2)	0.34089 (15)	0.0209 (4)
C2	0.5770 (3)	0.5734 (2)	0.25475 (15)	0.0226 (5)
C3	0.5067 (3)	0.6111 (3)	0.19077 (17)	0.0316 (5)
H3	0.4147	0.6209	0.1997	0.038*
C4	0.5740 (4)	0.6338 (3)	0.11420 (19)	0.0421 (7)
H4	0.5284	0.6602	0.0712	0.051*
C5	0.7756 (4)	0.5802 (3)	0.1610 (2)	0.0432 (7)
H5	0.8660	0.5686	0.1494	0.052*
C6	0.7134 (3)	0.5586 (3)	0.23913 (19)	0.0331 (6)
H6	0.7626	0.5341	0.2815	0.040*
C7	0.5896 (3)	0.7590 (2)	0.58623 (15)	0.0212 (4)
C8	0.6542 (3)	0.9101 (2)	0.63494 (16)	0.0231 (5)
C9	0.5830 (3)	0.9941 (3)	0.6193 (2)	0.0358 (6)
H9	0.4924	0.9581	0.5800	0.043*
C10	0.6474 (4)	1.1312 (3)	0.6624 (2)	0.0416 (7)
H10	0.6011	1.1889	0.6520	0.050*
C11	0.8452 (4)	1.1036 (3)	0.7370 (2)	0.0510 (8)
H11	0.9340	1.1423	0.7781	0.061*
C12	0.7861 (3)	0.9652 (3)	0.6950 (2)	0.0386 (7)
H12	0.8347	0.9101	0.7071	0.046*
C13	−0.0791 (2)	0.3637 (2)	0.35190 (15)	0.0189 (4)
C14	−0.1596 (3)	0.2516 (2)	0.26504 (15)	0.0214 (4)
C15	−0.3153 (3)	0.2093 (3)	0.24151 (18)	0.0316 (6)
H15	−0.3706	0.2529	0.2772	0.038*
C16	−0.3860 (4)	0.1024 (3)	0.1649 (2)	0.0432 (7)
H16	−0.4903	0.0716	0.1489	0.052*
C17	−0.1552 (4)	0.0837 (3)	0.13243 (19)	0.0426 (7)
H17	−0.1023	0.0413	0.0934	0.051*
C18	−0.0790 (3)	0.1880 (3)	0.20941 (17)	0.0314 (5)
H18	0.0252	0.2155	0.2239	0.038*
Cl1	0.19389 (9)	0.70180 (8)	0.03011 (5)	0.04494 (17)
Cl2	0.29246 (9)	0.22081 (7)	0.09772 (5)	0.04040 (16)
N1	0.7053 (3)	0.6179 (3)	0.10183 (17)	0.0461 (7)
H1	0.7463	0.6327	0.0536	0.055*
N2	0.7759 (3)	1.1812 (2)	0.71899 (18)	0.0424 (6)
H2	0.8156	1.2674	0.7449	0.051*
N3	−0.3051 (3)	0.0434 (2)	0.11387 (16)	0.0438 (6)
H3A	−0.3514	−0.0242	0.0665	0.053*
O1	0.3135 (4)	0.8310 (3)	0.0649 (2)	0.0980 (12)
O2	0.1590 (4)	0.6721 (3)	−0.06629 (17)	0.0719 (8)
O3	0.0636 (3)	0.7009 (3)	0.0738 (2)	0.0740 (8)
O4	0.2370 (4)	0.5967 (3)	0.0487 (2)	0.0825 (9)
O5	0.4033 (3)	0.2007 (3)	0.03987 (17)	0.0615 (7)
O6	0.2468 (4)	0.3225 (3)	0.0772 (2)	0.0801 (9)
O7	0.3532 (4)	0.2641 (3)	0.19129 (16)	0.0728 (8)
O8	0.1675 (3)	0.0947 (3)	0.0809 (2)	0.0852 (10)
O13	0.37551 (18)	0.54575 (17)	0.34757 (11)	0.0256 (3)
O14	0.58826 (19)	0.53420 (17)	0.40081 (11)	0.0272 (4)
O15	0.45551 (18)	0.70996 (16)	0.54760 (12)	0.0265 (4)
O16	0.67592 (18)	0.69729 (16)	0.58981 (12)	0.0259 (4)
O17	−0.14890 (19)	0.43444 (17)	0.39150 (11)	0.0275 (4)
O18	0.05161 (18)	0.37668 (17)	0.37767 (12)	0.0281 (4)
Tb1	0.270670 (11)	0.491645 (10)	0.483309 (7)	0.01654 (4)
O1W	0.1147 (2)	0.53818 (19)	0.22458 (14)	0.0412 (5)
H1W	0.1025	0.4998	0.1681	0.062*
H2W	0.1711	0.5100	0.2502	0.062*
O2W	0.18165 (19)	0.66276 (17)	0.44776 (12)	0.0298 (4)
H4W	0.0905	0.6479	0.4333	0.045*
H3W	0.2191	0.7391	0.4861	0.045*
O3W	0.0974 (2)	0.28637 (18)	0.52869 (13)	0.0323 (4)
H5W	0.1357	0.2549	0.5636	0.048*
H6W	0.0490	0.2213	0.4832	0.048*
Cl3	0.21484 (9)	0.04724 (7)	0.62478 (5)	0.04379 (17)	0.561 (17)
O9	0.3356 (12)	0.1332 (11)	0.5842 (9)	0.062 (3)	0.561 (17)
O10	0.3010 (12)	0.0741 (6)	0.7152 (4)	0.065 (2)	0.561 (17)
O11	0.1764 (12)	−0.0885 (8)	0.5784 (8)	0.066 (2)	0.561 (17)
O12	0.0975 (11)	0.0931 (12)	0.6326 (9)	0.109 (4)	0.561 (17)
Cl3'	0.21484 (9)	0.04724 (7)	0.62478 (5)	0.04379 (17)	0.439 (17)
O9'	0.2951 (16)	0.1488 (12)	0.5860 (10)	0.056 (3)	0.439 (17)
O10'	0.2119 (17)	0.0782 (8)	0.7181 (5)	0.070 (3)	0.439 (17)
O11'	0.2277 (15)	−0.0826 (11)	0.5862 (10)	0.065 (3)	0.439 (17)
O12'	0.0520 (9)	0.0154 (16)	0.5847 (10)	0.108 (4)	0.439 (17)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0267 (11)	0.0172 (10)	0.0180 (10)	0.0069 (9)	0.0022 (8)	0.0055 (8)
C2	0.0243 (11)	0.0208 (11)	0.0200 (11)	0.0060 (9)	0.0040 (9)	0.0047 (9)
C3	0.0322 (13)	0.0395 (14)	0.0264 (13)	0.0141 (11)	0.0057 (10)	0.0141 (11)
C4	0.0515 (18)	0.0481 (17)	0.0271 (14)	0.0144 (14)	0.0052 (12)	0.0180 (13)
C5	0.0402 (16)	0.0495 (18)	0.0404 (16)	0.0183 (14)	0.0189 (13)	0.0098 (14)
C6	0.0320 (13)	0.0383 (14)	0.0327 (14)	0.0170 (11)	0.0088 (11)	0.0104 (11)
C7	0.0236 (11)	0.0185 (10)	0.0199 (11)	0.0064 (9)	0.0062 (8)	0.0046 (8)
C8	0.0238 (11)	0.0186 (11)	0.0241 (11)	0.0067 (9)	0.0045 (9)	0.0028 (9)
C9	0.0327 (14)	0.0224 (12)	0.0481 (17)	0.0093 (11)	−0.0036 (12)	0.0052 (11)
C10	0.0456 (17)	0.0229 (13)	0.0564 (19)	0.0149 (12)	0.0067 (14)	0.0085 (12)
C11	0.0418 (17)	0.0331 (16)	0.058 (2)	0.0070 (13)	−0.0149 (15)	−0.0099 (14)
C12	0.0378 (15)	0.0268 (13)	0.0439 (16)	0.0129 (11)	−0.0090 (12)	−0.0022 (12)
C13	0.0198 (10)	0.0184 (10)	0.0178 (10)	0.0056 (8)	0.0013 (8)	0.0065 (8)
C14	0.0254 (11)	0.0209 (11)	0.0174 (10)	0.0083 (9)	0.0008 (8)	0.0054 (9)
C15	0.0279 (13)	0.0347 (14)	0.0271 (13)	0.0088 (11)	−0.0016 (10)	0.0050 (11)
C16	0.0391 (16)	0.0383 (16)	0.0384 (16)	0.0031 (13)	−0.0131 (12)	0.0062 (13)
C17	0.065 (2)	0.0353 (15)	0.0265 (14)	0.0237 (14)	0.0060 (13)	−0.0009 (12)
C18	0.0370 (14)	0.0313 (13)	0.0256 (12)	0.0154 (11)	0.0048 (10)	0.0041 (10)
Cl1	0.0505 (4)	0.0462 (4)	0.0342 (4)	0.0140 (3)	0.0078 (3)	0.0105 (3)
Cl2	0.0534 (4)	0.0382 (4)	0.0268 (3)	0.0162 (3)	0.0091 (3)	0.0056 (3)
N1	0.0547 (16)	0.0498 (15)	0.0274 (12)	0.0105 (13)	0.0208 (11)	0.0122 (11)
N2	0.0426 (14)	0.0191 (11)	0.0502 (15)	0.0027 (10)	0.0063 (11)	−0.0033 (10)
N3	0.0626 (17)	0.0297 (12)	0.0244 (12)	0.0088 (12)	−0.0121 (11)	−0.0029 (9)
O1	0.076 (2)	0.072 (2)	0.092 (2)	−0.0128 (16)	0.0228 (18)	−0.0111 (17)
O2	0.122 (2)	0.0698 (18)	0.0360 (13)	0.0448 (17)	0.0139 (14)	0.0228 (12)
O3	0.0541 (15)	0.089 (2)	0.0655 (17)	0.0209 (14)	0.0186 (13)	0.0063 (15)
O4	0.112 (3)	0.099 (2)	0.0642 (18)	0.065 (2)	0.0037 (17)	0.0356 (17)
O5	0.0657 (16)	0.0725 (17)	0.0480 (14)	0.0280 (13)	0.0226 (12)	0.0155 (12)
O6	0.116 (3)	0.091 (2)	0.0670 (18)	0.068 (2)	0.0267 (17)	0.0357 (17)
O7	0.112 (2)	0.0620 (16)	0.0280 (12)	0.0186 (16)	0.0000 (13)	0.0070 (11)
O8	0.0703 (19)	0.0567 (17)	0.089 (2)	−0.0050 (14)	0.0157 (16)	−0.0055 (15)
O13	0.0243 (8)	0.0332 (9)	0.0235 (8)	0.0135 (7)	0.0070 (6)	0.0111 (7)
O14	0.0298 (9)	0.0293 (9)	0.0227 (8)	0.0099 (7)	−0.0030 (7)	0.0102 (7)
O15	0.0225 (8)	0.0180 (8)	0.0336 (9)	0.0046 (6)	−0.0021 (7)	0.0027 (7)
O16	0.0263 (9)	0.0224 (8)	0.0297 (9)	0.0125 (7)	0.0043 (7)	0.0034 (7)
O17	0.0313 (9)	0.0303 (9)	0.0231 (8)	0.0173 (7)	0.0062 (7)	0.0026 (7)
O18	0.0218 (8)	0.0278 (9)	0.0296 (9)	0.0086 (7)	−0.0055 (7)	0.0014 (7)
Tb1	0.01613 (6)	0.01654 (6)	0.01645 (6)	0.00657 (4)	0.00083 (4)	0.00326 (4)
O1W	0.0515 (12)	0.0314 (10)	0.0364 (11)	0.0131 (9)	−0.0026 (9)	0.0068 (8)
O2W	0.0266 (9)	0.0266 (9)	0.0377 (10)	0.0130 (7)	0.0011 (7)	0.0073 (8)
O3W	0.0319 (9)	0.0255 (9)	0.0367 (10)	0.0071 (7)	0.0033 (8)	0.0094 (8)
Cl3	0.0564 (4)	0.0332 (3)	0.0465 (4)	0.0181 (3)	0.0120 (3)	0.0168 (3)
O9	0.067 (5)	0.052 (4)	0.069 (4)	0.017 (3)	0.020 (3)	0.026 (3)
O10	0.092 (5)	0.047 (3)	0.042 (3)	0.007 (3)	−0.009 (3)	0.018 (2)
O11	0.069 (5)	0.027 (3)	0.081 (4)	0.006 (3)	−0.027 (4)	−0.001 (2)
O12	0.083 (5)	0.120 (7)	0.144 (7)	0.066 (5)	0.042 (5)	0.029 (5)
Cl3'	0.0564 (4)	0.0332 (3)	0.0465 (4)	0.0181 (3)	0.0120 (3)	0.0168 (3)
O9'	0.075 (6)	0.035 (4)	0.056 (4)	0.012 (4)	0.018 (4)	0.024 (3)
O10'	0.101 (7)	0.052 (4)	0.049 (4)	0.020 (4)	0.018 (4)	0.016 (3)
O11'	0.067 (6)	0.041 (4)	0.078 (6)	0.022 (4)	−0.002 (5)	0.000 (3)
O12'	0.063 (5)	0.128 (8)	0.129 (8)	0.051 (5)	0.002 (5)	0.008 (6)

Geometric parameters (Å, º)

C1—O13	1.251 (3)	Cl1—O2	1.416 (3)
C1—O14	1.255 (3)	Cl1—O1	1.419 (3)
C1—C2	1.515 (3)	Cl1—O3	1.419 (3)
C2—C6	1.385 (3)	Cl1—O4	1.438 (3)
C2—C3	1.386 (3)	Cl2—O7	1.411 (2)
C3—C4	1.372 (4)	Cl2—O8	1.419 (3)
C3—H3	0.9300	Cl2—O6	1.428 (3)
C4—N1	1.336 (4)	Cl2—O5	1.432 (2)
C4—H4	0.9300	N1—H1	0.8600
C5—N1	1.332 (4)	N2—H2	0.8600
C5—C6	1.370 (4)	N3—H3A	0.8600
C5—H5	0.9300	O13—Tb1	2.4189 (16)
C6—H6	0.9300	O14—Tb1^i	2.3152 (16)
C7—O16	1.246 (3)	O15—Tb1	2.3406 (15)
C7—O15	1.254 (3)	O16—Tb1^i	2.3268 (16)
C7—C8	1.515 (3)	O17—Tb1^ii	2.3702 (16)
C8—C12	1.375 (4)	O18—Tb1	2.3293 (15)
C8—C9	1.383 (4)	Tb1—O14^i	2.3152 (16)
C9—C10	1.372 (4)	Tb1—O16^i	2.3268 (16)
C9—H9	0.9300	Tb1—O17^ii	2.3701 (16)
C10—N2	1.327 (4)	Tb1—O2W	2.4789 (17)
C10—H10	0.9300	Tb1—O3W	2.5292 (17)
C11—N2	1.321 (4)	O1W—H1W	0.8376
C11—C12	1.380 (4)	O1W—H2W	0.8389
C11—H11	0.9300	O2W—H4W	0.8361
C12—H12	0.9300	O2W—H3W	0.8339
C13—O18	1.242 (3)	O3W—H5W	0.8383
C13—O17	1.250 (3)	O3W—H6W	0.8343
C13—C14	1.512 (3)	Cl3—O10'	1.371 (7)
C14—C18	1.382 (3)	Cl3—O12	1.378 (6)
C14—C15	1.391 (3)	Cl3—O9'	1.378 (9)
C15—C16	1.372 (4)	Cl3—O11	1.382 (8)
C15—H15	0.9300	Cl3—O11'	1.447 (9)
C16—N3	1.323 (4)	Cl3—O9	1.459 (8)
C16—H16	0.9300	Cl3—O10	1.484 (6)
C17—N3	1.333 (4)	Cl3—O12'	1.534 (8)
C17—C18	1.373 (4)	O10—O10'	0.867 (9)
C17—H17	0.9300	O12—O12'	0.921 (10)
C18—H18	0.9300	O12—O10'	1.745 (12)
O13—C1—O14	124.7 (2)	C17—N3—H3A	118.5
O13—C1—C2	118.7 (2)	C1—O13—Tb1	115.63 (14)
O14—C1—C2	116.6 (2)	C1—O14—Tb1^i	177.12 (16)
C6—C2—C3	118.9 (2)	C7—O15—Tb1	136.30 (15)
C6—C2—C1	120.1 (2)	C7—O16—Tb1^i	144.47 (15)
C3—C2—C1	121.0 (2)	C13—O17—Tb1^ii	152.03 (16)
C4—C3—C2	119.5 (3)	C13—O18—Tb1	148.90 (15)
C4—C3—H3	120.3	O14^i—Tb1—O16^i	76.86 (6)
C2—C3—H3	120.3	O14^i—Tb1—O18	142.30 (6)
N1—C4—C3	119.6 (3)	O16^i—Tb1—O18	81.76 (6)
N1—C4—H4	120.2	O14^i—Tb1—O15	75.81 (6)
C3—C4—H4	120.2	O16^i—Tb1—O15	124.12 (6)
N1—C5—C6	119.4 (3)	O18—Tb1—O15	141.36 (6)
N1—C5—H5	120.3	O14^i—Tb1—O17^ii	81.73 (6)
C6—C5—H5	120.3	O16^i—Tb1—O17^ii	140.19 (6)
C5—C6—C2	119.8 (3)	O18—Tb1—O17^ii	95.97 (6)
C5—C6—H6	120.1	O15—Tb1—O17^ii	81.27 (6)
C2—C6—H6	120.1	O14^i—Tb1—O13	122.25 (6)
O16—C7—O15	127.4 (2)	O16^i—Tb1—O13	76.08 (6)
O16—C7—C8	116.1 (2)	O18—Tb1—O13	81.06 (6)
O15—C7—C8	116.6 (2)	O15—Tb1—O13	78.95 (6)
C12—C8—C9	119.3 (2)	O17^ii—Tb1—O13	143.18 (6)
C12—C8—C7	119.7 (2)	O14^i—Tb1—O2W	140.16 (6)
C9—C8—C7	121.0 (2)	O16^i—Tb1—O2W	140.79 (6)
C10—C9—C8	119.3 (3)	O18—Tb1—O2W	71.74 (6)
C10—C9—H9	120.3	O15—Tb1—O2W	70.71 (6)
C8—C9—H9	120.3	O17^ii—Tb1—O2W	72.52 (6)
N2—C10—C9	119.7 (3)	O13—Tb1—O2W	71.74 (6)
N2—C10—H10	120.1	O14^i—Tb1—O3W	73.90 (6)
C9—C10—H10	120.1	O16^i—Tb1—O3W	71.06 (6)
N2—C11—C12	120.1 (3)	O18—Tb1—O3W	69.91 (6)
N2—C11—H11	120.0	O15—Tb1—O3W	141.20 (6)
C12—C11—H11	120.0	O17^ii—Tb1—O3W	70.93 (6)
C8—C12—C11	119.0 (3)	O13—Tb1—O3W	138.50 (6)
C8—C12—H12	120.5	O2W—Tb1—O3W	122.65 (6)
C11—C12—H12	120.5	H1W—O1W—H2W	107.2
O18—C13—O17	125.8 (2)	Tb1—O2W—H4W	123.7
O18—C13—C14	116.4 (2)	Tb1—O2W—H3W	113.6
O17—C13—C14	117.84 (19)	H4W—O2W—H3W	107.2
C18—C14—C15	119.4 (2)	Tb1—O3W—H5W	118.0
C18—C14—C13	120.0 (2)	Tb1—O3W—H6W	112.5
C15—C14—C13	120.6 (2)	H5W—O3W—H6W	106.9
C16—C15—C14	119.1 (3)	O10'—Cl3—O12	78.8 (5)
C16—C15—H15	120.5	O10'—Cl3—O9'	119.3 (7)
C14—C15—H15	120.5	O12—Cl3—O9'	91.0 (7)
N3—C16—C15	119.7 (3)	O10'—Cl3—O11	117.0 (7)
N3—C16—H16	120.2	O12—Cl3—O11	116.2 (5)
C15—C16—H16	120.2	O9'—Cl3—O11	121.0 (9)
N3—C17—C18	119.7 (3)	O10'—Cl3—O11'	113.6 (7)
N3—C17—H17	120.1	O12—Cl3—O11'	135.4 (6)
C18—C17—H17	120.1	O9'—Cl3—O11'	114.8 (8)
C17—C18—C14	119.0 (3)	O10'—Cl3—O9	121.1 (7)
C17—C18—H18	120.5	O12—Cl3—O9	110.0 (5)
C14—C18—H18	120.5	O11—Cl3—O9	110.2 (6)
O2—Cl1—O1	110.4 (2)	O11'—Cl3—O9	99.6 (8)
O2—Cl1—O3	109.95 (19)	O12—Cl3—O10	112.4 (4)
O1—Cl1—O3	109.64 (19)	O9'—Cl3—O10	107.3 (8)
O2—Cl1—O4	108.26 (17)	O11—Cl3—O10	108.0 (5)
O1—Cl1—O4	110.4 (2)	O11'—Cl3—O10	94.6 (6)
O3—Cl1—O4	108.2 (2)	O9—Cl3—O10	98.6 (6)
O7—Cl2—O8	108.89 (19)	O10'—Cl3—O12'	104.2 (6)
O7—Cl2—O6	109.02 (18)	O9'—Cl3—O12'	100.7 (7)
O8—Cl2—O6	111.1 (2)	O11—Cl3—O12'	81.5 (6)
O7—Cl2—O5	110.65 (18)	O11'—Cl3—O12'	100.6 (5)
O8—Cl2—O5	108.17 (17)	O9—Cl3—O12'	116.1 (6)
O6—Cl2—O5	109.06 (17)	O10—Cl3—O12'	138.6 (5)
C5—N1—C4	122.8 (2)	O10'—O10—Cl3	65.4 (6)
C5—N1—H1	118.6	O12'—O12—Cl3	81.1 (7)
C4—N1—H1	118.6	O12'—O12—O10'	115.2 (10)
C11—N2—C10	122.6 (2)	Cl3—O12—O10'	50.4 (3)
C11—N2—H2	118.7	O10—O10'—Cl3	79.5 (7)
C10—N2—H2	118.7	O10—O10'—O12	127.9 (9)
C16—N3—C17	123.1 (2)	Cl3—O10'—O12	50.8 (4)
C16—N3—H3A	118.5	O12—O12'—Cl3	62.5 (6)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O6^iii	0.86	2.15	2.949 (4)	154
N2—H2···O1W^iv	0.86	1.91	2.756 (3)	166
N3—H3A···O5^v	0.86	2.07	2.902 (3)	162
O1W—H1W···O4	0.84	2.48	3.054 (4)	127
O1W—H2W···O13	0.84	2.26	3.030 (3)	152
O2W—H4W···O3W^ii	0.84	2.20	2.920 (3)	145
O2W—H4W···O17	0.84	2.53	3.164 (2)	133
O2W—H3W···O11^vi	0.83	2.23	2.959 (9)	147
O3W—H5W···O12	0.84	2.20	2.934 (9)	146
O3W—H6W···O11^vii	0.83	2.14	2.843 (9)	142

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