catena-Poly[[[diaqua-terbium(III)]-tri-μ(2)-isonicotinato-κO:O'] tris(perchlorate) monohydrate].

In the title complex, {[Tb(C(6)H(5)NO(2))(3)(H(2)O)(2)](ClO(4))(3)·H(2)O}(n), the Tb(III) ion is coordinated by six O atoms from six isonicotinate (inic) ligands and two water mol-ecules, 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 inter-molecular O-H⋯O and N-H⋯O hydrogen-bonding inter-actions into a three-dimensional supra-molecular network involving the inic ligands, the water mol-ecules and the perchlorate anions. One of the perchlorate ions is disordered over two sites with occupancies of 0.561 (17) and 0.439 (17).

Related literature

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

Experimental

Crystal data

[Tb(C6H5NO2)3(H2O)2](ClO4)3·H2O

M = 880.65

Triclinic,

a = 9.5270 (4) Å

b = 10.9508 (4) Å

c = 15.1309 (6) Å

α = 104.402 (2)°

β = 91.480 (2)°

γ = 111.159 (2)°

V = 1414.17 (10) Å3

Z = 2

Mo Kα radiation

μ = 2.88 mm−1

T = 296 (2) K

0.20 × 0.18 × 0.15 mm

Data collection

Bruker APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS, Sheldrick, 1996 ▶) T min = 0.566, T max = 0.645

19700 measured reflections

6605 independent reflections

6206 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.021

wR(F 2) = 0.048

S = 1.04

6605 reflections

452 parameters

77 restraints

H-atom parameters constrained

Δρmax = 0.94 e Å−3

Δρmin = −0.79 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2; 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808023623/rz2238sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808023623/rz2238Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Tb(C6H5NO2)3(H2O)2](ClO4)3·H2O	Z = 2
Mr = 880.65	F000 = 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 = 1.7–28.0º
c = 15.1309 (6) Å	µ = 2.88 mm−1
α = 104.402 (2)º	T = 296 (2) K
β = 91.480 (2)º	Block, colourless
γ = 111.159 (2)º	0.20 × 0.18 × 0.15 mm
V = 1414.17 (10) Å3

Bruker APEXII area-detector diffractometer	6605 independent reflections
Radiation source: fine-focus sealed tube	6206 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.024
T = 296(2) K	θmax = 27.8º
φ and ω scan	θmin = 2.1º
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 on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.021	H-atom parameters constrained
wR(F2) = 0.048	w = 1/[σ2(Fo2) + (0.021P)2 + 1.1255P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
6605 reflections	Δρmax = 0.95 e Å−3
452 parameters	Δρmin = −0.79 e Å−3
77 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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.

	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)

	U11	U22	U33	U12	U13	U23
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)

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—Tb1i	2.3152 (16)
C7—O16	1.246 (3)	O15—Tb1	2.3406 (15)
C7—O15	1.254 (3)	O16—Tb1i	2.3268 (16)
C7—C8	1.515 (3)	O17—Tb1ii	2.3702 (16)
C8—C12	1.375 (4)	O18—Tb1	2.3293 (15)
C8—C9	1.383 (4)	Tb1—O14i	2.3152 (16)
C9—C10	1.372 (4)	Tb1—O16i	2.3268 (16)
C9—H9	0.9300	Tb1—O17ii	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—Tb1i	177.12 (16)
C6—C2—C3	118.9 (2)	C7—O15—Tb1	136.30 (15)
C6—C2—C1	120.1 (2)	C7—O16—Tb1i	144.47 (15)
C3—C2—C1	121.0 (2)	C13—O17—Tb1ii	152.03 (16)
C4—C3—C2	119.5 (3)	C13—O18—Tb1	148.90 (15)
C4—C3—H3	120.3	O14i—Tb1—O16i	76.86 (6)
C2—C3—H3	120.3	O14i—Tb1—O18	142.30 (6)
N1—C4—C3	119.6 (3)	O16i—Tb1—O18	81.76 (6)
N1—C4—H4	120.2	O14i—Tb1—O15	75.81 (6)
C3—C4—H4	120.2	O16i—Tb1—O15	124.12 (6)
N1—C5—C6	119.4 (3)	O18—Tb1—O15	141.36 (6)
N1—C5—H5	120.3	O14i—Tb1—O17ii	81.73 (6)
C6—C5—H5	120.3	O16i—Tb1—O17ii	140.19 (6)
C5—C6—C2	119.8 (3)	O18—Tb1—O17ii	95.97 (6)
C5—C6—H6	120.1	O15—Tb1—O17ii	81.27 (6)
C2—C6—H6	120.1	O14i—Tb1—O13	122.25 (6)
O16—C7—O15	127.4 (2)	O16i—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)	O17ii—Tb1—O13	143.18 (6)
C12—C8—C7	119.7 (2)	O14i—Tb1—O2W	140.16 (6)
C9—C8—C7	121.0 (2)	O16i—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	O17ii—Tb1—O2W	72.52 (6)
N2—C10—C9	119.7 (3)	O13—Tb1—O2W	71.74 (6)
N2—C10—H10	120.1	O14i—Tb1—O3W	73.90 (6)
C9—C10—H10	120.1	O16i—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	O17ii—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)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O6iii	0.86	2.15	2.949 (4)	154
N2—H2···O1Wiv	0.86	1.91	2.756 (3)	166
N3—H3A···O5v	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···O3Wii	0.84	2.20	2.920 (3)	145
O2W—H4W···O17	0.84	2.53	3.164 (2)	133
O2W—H3W···O11vi	0.83	2.23	2.959 (9)	147
O3W—H5W···O12	0.84	2.20	2.934 (9)	146
O3W—H6W···O11vii	0.83	2.14	2.843 (9)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O6i	0.86	2.15	2.949 (4)	154
N2—H2⋯O1Wii	0.86	1.91	2.756 (3)	166
N3—H3A⋯O5iii	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⋯O3Wiv	0.84	2.20	2.920 (3)	145
O2W—H4W⋯O17	0.84	2.53	3.164 (2)	133
O2W—H3W⋯O11v	0.83	2.23	2.959 (9)	147
O3W—H5W⋯O12	0.84	2.20	2.934 (9)	146
O3W—H6W⋯O11vi	0.83	2.14	2.843 (9)	142

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .