Poly[[diaqua-tris-(μ(2)-3-methyl-pyridine-2-carboxyl-ato)(3-methyl-pyridine-2-car-boxyl-ato)sodiumterbium(III)] ethanol monosolvate monohydrate].

In the title compound, {[NaTb(C(7)H(6)NO(2))(4)(H(2)O)(2)]·C(2)H(5)OH·H(2)O}(n), the Tb(III) atom is eight-coordinated in a slightly distorted square-anti-prismatic geometry defined by four carboxyl-ate O atoms and four pyridine N atoms. The bond lengths lie within the range 2.3000 (2)-2.326 (2) Å for the Tb-O bonds and 2.543 (3)-2.553 (3) Å for the Tb-N bonds. The Na(I) atom is five-coordinated by two water O atoms and three carboxyl-ate O atoms in a distorted square-pyramidal geometry. In the crystal, inter-molecular O-H⋯O hydrogen bonds link the mol-ecules into a three-dimensional network.

Related literature

For general background to luminescent compounds, see: Fan et al. (2009 ▶); Oh et al. (2010 ▶); Seo et al. (2010 ▶); Zhou et al. (2010 ▶). For luminescence properties of metal compounds, see: Godlewska et al. (2008 ▶); Kang (2010 ▶); Kim et al. (2010 ▶); Legendziewicz (2002 ▶); Lis et al. (2009 ▶); Seo et al. (2009 ▶).

Experimental

Crystal data

[NaTb(C7H6NO2)4(H2O)2]·C2H6O·H2O

M = 826.54

Orthorhombic,

a = 18.4662 (6) Å

b = 18.5290 (5) Å

c = 9.8939 (3) Å

V = 3385.30 (18) Å3

Z = 4

Mo Kα radiation

μ = 2.17 mm−1

T = 174 K

0.16 × 0.11 × 0.07 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.704, T max = 0.856

44141 measured reflections

6652 independent reflections

5995 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.022

wR(F 2) = 0.045

S = 1.07

6652 reflections

460 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.51 e Å−3

Δρmin = −0.56 e Å−3

Absolute structure: Flack (1983 ▶), 2234 Friedel pairs

Flack parameter: 0.001 (6)

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2010 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810038456/is2603sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810038456/is2603Isup2.hkl

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

[NaTb(C7H6NO2)4(H2O)2]·C2H6O·H2O	F(000) = 1664
Mr = 826.54	Dx = 1.622 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 9041 reflections
a = 18.4662 (6) Å	θ = 2.3–28.2°
b = 18.5290 (5) Å	µ = 2.17 mm−1
c = 9.8939 (3) Å	T = 174 K
V = 3385.30 (18) Å3	Block, colourless
Z = 4	0.16 × 0.11 × 0.07 mm

Bruker SMART CCD area-detector diffractometer	5995 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.038
Absorption correction: multi-scan (SADABS; Bruker, 2002)	θmax = 28.3°, θmin = 1.6°
Tmin = 0.704, Tmax = 0.856	h = −24→20
44141 measured reflections	k = −18→24
6652 independent reflections	l = −13→8

Refinement on F2	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.0185P)2 + 0.0181P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.022	(Δ/σ)max = 0.004
wR(F2) = 0.045	Δρmax = 0.51 e Å−3
S = 1.07	Δρmin = −0.56 e Å−3
6652 reflections	Absolute structure: Flack (1983), 2234 Friedel pairs
460 parameters	Flack parameter: 0.001 (6)
6 restraints

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.

	x	y	z	Uiso*/Ueq
Tb1	0.878991 (6)	0.769501 (6)	0.19856 (3)	0.01726 (4)
N1	0.75484 (13)	0.80674 (13)	0.1090 (2)	0.0206 (5)
C2	0.74647 (16)	0.87607 (16)	0.0698 (3)	0.0218 (6)
C3	0.68063 (18)	0.90306 (18)	0.0214 (3)	0.0302 (8)
C4	0.62409 (18)	0.8540 (2)	0.0116 (4)	0.0331 (9)
H4	0.5794	0.8695	−0.0209	0.04*
C5	0.63268 (17)	0.7836 (2)	0.0487 (3)	0.0304 (8)
H5	0.5945	0.751	0.0412	0.036*
C6	0.69877 (17)	0.76174 (18)	0.0972 (3)	0.0264 (7)
H6	0.7047	0.7138	0.1227	0.032*
C7	0.81601 (17)	0.91984 (16)	0.0816 (3)	0.0262 (7)
O8	0.86652 (10)	0.89129 (11)	0.1516 (2)	0.0254 (5)
O9	0.82067 (13)	0.97871 (12)	0.0241 (3)	0.0380 (6)
C10	0.6682 (2)	0.9806 (2)	−0.0189 (5)	0.0563 (12)
H10A	0.6886	0.989	−0.1068	0.084*
H10B	0.6911	1.0119	0.0457	0.084*
H10C	0.6172	0.9904	−0.0211	0.084*
N11	0.94179 (14)	0.77843 (13)	−0.0307 (2)	0.0242 (6)
C12	0.93444 (17)	0.72055 (16)	−0.1136 (3)	0.0240 (7)
C13	0.9646 (2)	0.71841 (19)	−0.2442 (3)	0.0331 (9)
C14	1.0026 (2)	0.77989 (19)	−0.2830 (4)	0.0407 (10)
H14	1.0233	0.7813	−0.3687	0.049*
C15	1.01063 (19)	0.8380 (2)	−0.2005 (4)	0.0404 (9)
H15	1.0366	0.8783	−0.2285	0.049*
C16	0.97899 (18)	0.83566 (18)	−0.0733 (3)	0.0316 (8)
H16	0.9839	0.8752	−0.0161	0.038*
C17	0.89107 (17)	0.65991 (18)	−0.0524 (3)	0.0231 (7)
O18	0.85345 (12)	0.67662 (11)	0.0515 (2)	0.0233 (5)
O19	0.89462 (13)	0.59921 (13)	−0.1012 (2)	0.0421 (6)
C20	0.9552 (2)	0.6564 (2)	−0.3396 (3)	0.0529 (12)
H20A	0.9923	0.6211	−0.3232	0.079*
H20B	0.9588	0.6734	−0.431	0.079*
H20C	0.9085	0.6349	−0.3257	0.079*
N21	0.97062 (13)	0.67355 (13)	0.2657 (2)	0.0218 (6)
C22	1.03261 (16)	0.69539 (16)	0.3236 (3)	0.0194 (6)
C23	1.08422 (19)	0.64699 (18)	0.3738 (3)	0.0252 (8)
C24	1.06794 (18)	0.57326 (18)	0.3599 (3)	0.0321 (8)
H24	1.1007	0.5391	0.3917	0.039*
C25	1.00540 (19)	0.55083 (17)	0.3009 (4)	0.0355 (9)
H25	0.9954	0.5019	0.2915	0.043*
C26	0.95664 (18)	0.60265 (16)	0.2549 (3)	0.0311 (8)
H26	0.9133	0.5878	0.2157	0.037*
C27	1.04130 (17)	0.77676 (15)	0.3275 (3)	0.0211 (7)
O28	0.99116 (11)	0.81287 (11)	0.2681 (2)	0.0216 (5)
O29	1.09365 (13)	0.80420 (12)	0.3846 (2)	0.0337 (5)
C30	1.1533 (2)	0.66829 (19)	0.4411 (4)	0.0365 (9)
H30A	1.1797	0.7007	0.3835	0.055*
H30B	1.182	0.626	0.4579	0.055*
H30C	1.1428	0.6919	0.5253	0.055*
N31	0.85257 (14)	0.81025 (13)	0.4399 (2)	0.0214 (5)
C32	0.81292 (16)	0.76643 (16)	0.5184 (3)	0.0209 (7)
C33	0.79403 (18)	0.78474 (18)	0.6512 (3)	0.0280 (8)
C34	0.81700 (15)	0.85172 (17)	0.6973 (5)	0.0374 (7)
H34	0.8048	0.8663	0.7843	0.045*
C35	0.85745 (19)	0.8969 (2)	0.6171 (3)	0.0376 (9)
H35	0.8725	0.9417	0.6486	0.045*
C36	0.87514 (16)	0.87394 (18)	0.4880 (4)	0.0298 (8)
H36	0.9034	0.9035	0.4334	0.036*
C37	0.78728 (16)	0.69799 (17)	0.4476 (3)	0.0213 (7)
O38	0.80812 (12)	0.69262 (11)	0.3243 (2)	0.0254 (5)
O39	0.74967 (12)	0.65377 (12)	0.5063 (2)	0.0306 (5)
C40	0.7506 (2)	0.7367 (2)	0.7431 (3)	0.0462 (11)
H40A	0.748	0.7579	0.8315	0.069*
H40B	0.7734	0.6902	0.7491	0.069*
H40C	0.7025	0.7312	0.7075	0.069*
Na41	0.84271 (7)	1.08389 (6)	−0.09718 (12)	0.0286 (3)
O42	0.77005 (16)	1.07464 (14)	−0.2808 (3)	0.0468 (7)
H42A	0.764 (2)	1.058 (2)	−0.356 (3)	0.056*
H42B	0.7432 (18)	1.1072 (16)	−0.257 (3)	0.056*
O43	0.96139 (14)	1.04567 (12)	−0.1891 (2)	0.0340 (6)
H43A	0.9724 (19)	1.0870 (11)	−0.209 (3)	0.041*
H43B	0.9744 (18)	1.0202 (16)	−0.250 (3)	0.041*
O44	0.97142 (17)	1.01756 (16)	0.0874 (3)	0.0452 (7)
H44A	0.941 (2)	0.988 (2)	0.098 (4)	0.052 (14)*
H44B	0.984 (2)	1.023 (2)	0.011 (4)	0.062 (15)*
C45	0.8279 (2)	1.0581 (3)	−0.6322 (5)	0.0689 (13)
H45A	0.854	1.0534	−0.7156	0.103*
H45B	0.8577	1.0418	−0.5588	0.103*
H45C	0.8152	1.1078	−0.6182	0.103*
C46	0.7615 (2)	1.0140 (2)	−0.6381 (4)	0.0559 (12)
H46A	0.7321	1.0304	−0.7134	0.067*
H46B	0.7748	0.9642	−0.6553	0.067*
O47	0.71951 (15)	1.01711 (15)	−0.5181 (3)	0.0495 (7)
H47	0.6882 (18)	1.0467 (18)	−0.525 (4)	0.059*

	U11	U22	U33	U12	U13	U23
Tb1	0.01829 (7)	0.01596 (6)	0.01754 (6)	−0.00143 (5)	0.00021 (9)	−0.00065 (11)
N1	0.0205 (14)	0.0203 (14)	0.0209 (12)	−0.0017 (11)	0.0016 (10)	−0.0017 (11)
C2	0.0209 (17)	0.0235 (16)	0.0210 (14)	0.0002 (13)	0.0029 (13)	0.0008 (13)
C3	0.0251 (19)	0.035 (2)	0.0305 (16)	0.0036 (16)	−0.0028 (14)	0.0067 (15)
C4	0.025 (2)	0.044 (2)	0.0305 (19)	0.0014 (18)	−0.0022 (16)	0.0036 (17)
C5	0.020 (2)	0.044 (2)	0.0280 (17)	−0.0083 (15)	0.0015 (14)	−0.0023 (15)
C6	0.026 (2)	0.0266 (17)	0.0266 (16)	−0.0051 (15)	0.0025 (14)	0.0011 (14)
C7	0.0258 (19)	0.0212 (17)	0.0316 (17)	−0.0033 (14)	0.0038 (14)	−0.0019 (14)
O8	0.0195 (12)	0.0218 (11)	0.0349 (12)	−0.0002 (9)	−0.0038 (9)	−0.0015 (9)
O9	0.0319 (14)	0.0284 (13)	0.0535 (15)	−0.0011 (11)	0.0010 (12)	0.0213 (12)
C10	0.036 (2)	0.048 (3)	0.085 (3)	0.006 (2)	−0.017 (2)	0.022 (2)
N11	0.0229 (16)	0.0250 (15)	0.0247 (13)	−0.0018 (12)	0.0002 (11)	0.0026 (11)
C12	0.0243 (19)	0.0261 (18)	0.0215 (15)	0.0066 (13)	0.0013 (13)	0.0045 (14)
C13	0.038 (2)	0.040 (2)	0.0216 (16)	0.0124 (17)	0.0079 (15)	0.0019 (15)
C14	0.047 (2)	0.049 (2)	0.025 (3)	0.0076 (16)	0.0158 (18)	0.0132 (18)
C15	0.034 (2)	0.044 (2)	0.044 (2)	0.0016 (17)	0.0119 (17)	0.0187 (19)
C16	0.030 (2)	0.0296 (18)	0.0351 (18)	−0.0032 (15)	0.0018 (15)	0.0073 (15)
C17	0.0228 (18)	0.0253 (17)	0.0213 (15)	0.0001 (13)	−0.0007 (13)	−0.0013 (13)
O18	0.0246 (12)	0.0231 (11)	0.0220 (10)	−0.0013 (10)	0.0031 (9)	−0.0037 (9)
O19	0.0596 (17)	0.0266 (13)	0.0401 (14)	−0.0064 (12)	0.0216 (13)	−0.0127 (12)
C20	0.085 (3)	0.047 (2)	0.026 (2)	0.017 (2)	0.0180 (18)	−0.0006 (16)
N21	0.0210 (15)	0.0175 (13)	0.0268 (13)	−0.0006 (11)	0.0006 (11)	0.0017 (10)
C22	0.0241 (18)	0.0160 (15)	0.0180 (13)	−0.0017 (13)	0.0026 (12)	0.0008 (12)
C23	0.025 (2)	0.0234 (17)	0.0274 (17)	0.0017 (15)	0.0017 (15)	0.0037 (14)
C24	0.0251 (19)	0.0253 (18)	0.046 (2)	0.0061 (15)	0.0007 (16)	0.0093 (16)
C25	0.037 (2)	0.0160 (17)	0.054 (2)	0.0014 (15)	−0.0021 (18)	0.0023 (16)
C26	0.030 (2)	0.0186 (16)	0.0453 (19)	−0.0021 (14)	−0.0054 (15)	0.0001 (14)
C27	0.0213 (18)	0.0237 (17)	0.0184 (14)	−0.0023 (13)	0.0035 (12)	0.0010 (13)
O28	0.0177 (11)	0.0172 (11)	0.0298 (11)	0.0004 (9)	−0.0021 (9)	0.0012 (9)
O29	0.0307 (14)	0.0242 (12)	0.0463 (14)	−0.0051 (11)	−0.0151 (12)	−0.0019 (11)
C30	0.034 (2)	0.032 (2)	0.043 (2)	0.0024 (17)	−0.0071 (17)	0.0057 (17)
N31	0.0195 (14)	0.0220 (14)	0.0227 (12)	0.0004 (12)	0.0016 (11)	−0.0036 (11)
C32	0.0148 (17)	0.0289 (17)	0.0192 (14)	−0.0007 (14)	0.0005 (12)	−0.0018 (13)
C33	0.0235 (19)	0.039 (2)	0.0215 (14)	−0.0012 (15)	−0.0014 (12)	0.0010 (13)
C34	0.0322 (17)	0.056 (2)	0.0234 (13)	−0.0029 (15)	0.003 (2)	−0.015 (3)
C35	0.039 (2)	0.036 (2)	0.038 (2)	−0.0087 (17)	0.0002 (17)	−0.0173 (17)
C36	0.026 (2)	0.0308 (18)	0.0329 (18)	−0.0072 (15)	0.0039 (14)	−0.0073 (15)
C37	0.0177 (17)	0.0253 (16)	0.0210 (14)	0.0039 (14)	−0.0012 (12)	0.0026 (13)
O38	0.0324 (14)	0.0240 (12)	0.0199 (10)	−0.0061 (10)	0.0037 (10)	−0.0026 (9)
O39	0.0327 (14)	0.0345 (13)	0.0246 (11)	−0.0096 (11)	0.0041 (10)	0.0056 (10)
C40	0.051 (3)	0.067 (3)	0.0206 (16)	−0.005 (2)	0.0059 (16)	−0.0044 (17)
Na41	0.0312 (8)	0.0212 (6)	0.0333 (7)	0.0014 (6)	0.0016 (6)	0.0032 (6)
O42	0.0501 (16)	0.0436 (16)	0.047 (2)	0.0212 (12)	−0.0120 (14)	−0.0133 (14)
O43	0.0413 (15)	0.0226 (13)	0.0382 (14)	−0.0012 (12)	0.0097 (12)	−0.0011 (11)
O44	0.0456 (19)	0.0522 (19)	0.0379 (16)	−0.0228 (15)	−0.0070 (14)	0.0054 (14)
C45	0.065 (3)	0.067 (3)	0.075 (3)	−0.007 (3)	0.012 (3)	−0.009 (3)
C46	0.052 (3)	0.063 (3)	0.053 (3)	0.006 (2)	0.001 (2)	−0.011 (2)
O47	0.052 (2)	0.0492 (18)	0.0470 (16)	0.0097 (14)	−0.0055 (14)	−0.0090 (14)

Tb1—O8	2.315 (2)	N21—C26	1.343 (4)
Tb1—O18	2.302 (2)	C22—C23	1.400 (4)
Tb1—O28	2.326 (2)	C22—C27	1.517 (4)
Tb1—O38	2.300 (2)	C23—C24	1.406 (4)
Tb1—N1	2.553 (2)	C23—C30	1.493 (5)
Tb1—N11	2.553 (3)	C24—C25	1.359 (4)
Tb1—N21	2.543 (2)	C24—H24	0.93
Tb1—N31	2.551 (2)	C25—C26	1.393 (4)
Na41—O9	2.324 (2)	C25—H25	0.93
Na41—O29i	2.390 (3)	C26—H26	0.93
Na41—O39ii	2.374 (2)	C27—O29	1.230 (4)
Na41—O42	2.265 (3)	C27—O28	1.285 (3)
Na41—O43	2.476 (3)	C30—H30A	0.96
N1—C6	1.334 (4)	C30—H30B	0.96
N1—C2	1.351 (4)	C30—H30C	0.96
C2—C3	1.399 (4)	N31—C36	1.339 (4)
C2—C7	1.523 (4)	N31—C32	1.341 (4)
C3—C4	1.387 (4)	C32—C33	1.401 (4)
C3—C10	1.509 (5)	C32—C37	1.524 (4)
C4—C5	1.366 (5)	C33—C34	1.389 (4)
C4—H4	0.93	C33—C40	1.505 (5)
C5—C6	1.372 (4)	C34—C35	1.374 (5)
C5—H5	0.93	C34—H34	0.93
C6—H6	0.93	C35—C36	1.385 (5)
C7—O9	1.233 (3)	C35—H35	0.93
C7—O8	1.277 (4)	C36—H36	0.93
C10—H10A	0.96	C37—O39	1.221 (3)
C10—H10B	0.96	C37—O38	1.283 (3)
C10—H10C	0.96	C40—H40A	0.96
N11—C16	1.332 (4)	C40—H40B	0.96
N11—C12	1.357 (3)	C40—H40C	0.96
C12—C13	1.408 (4)	O42—H42A	0.814 (18)
C12—C17	1.507 (4)	O42—H42B	0.814 (18)
C13—C14	1.392 (5)	O43—H43A	0.817 (18)
C13—C20	1.497 (5)	O43—H43B	0.806 (17)
C14—C15	1.360 (5)	O44—H44A	0.80 (4)
C14—H14	0.93	O44—H44B	0.80 (4)
C15—C16	1.388 (4)	C45—C46	1.474 (5)
C15—H15	0.93	C45—H45A	0.96
C16—H16	0.93	C45—H45B	0.96
C17—O19	1.226 (4)	C45—H45C	0.96
C17—O18	1.279 (3)	C46—O47	1.419 (5)
C20—H20A	0.96	C46—H46A	0.97
C20—H20B	0.96	C46—H46B	0.97
C20—H20C	0.96	O47—H47	0.800 (18)
N21—C22	1.343 (4)
O38—Tb1—O18	76.25 (7)	C22—N21—C26	119.5 (3)
O38—Tb1—O8	130.96 (7)	C22—N21—Tb1	117.91 (18)
O18—Tb1—O8	125.56 (7)	C26—N21—Tb1	122.4 (2)
O38—Tb1—O28	124.11 (7)	N21—C22—C23	122.6 (3)
O18—Tb1—O28	128.87 (7)	N21—C22—C27	113.6 (2)
O8—Tb1—O28	79.11 (7)	C23—C22—C27	123.8 (3)
O38—Tb1—N21	78.72 (8)	C22—C23—C24	116.2 (3)
O18—Tb1—N21	77.21 (8)	C22—C23—C30	124.8 (3)
O8—Tb1—N21	143.13 (7)	C24—C23—C30	118.9 (3)
O28—Tb1—N21	64.64 (7)	C25—C24—C23	121.4 (3)
O38—Tb1—N31	64.42 (7)	C25—C24—H24	119.3
O18—Tb1—N31	140.66 (8)	C23—C24—H24	119.3
O8—Tb1—N31	83.12 (8)	C24—C25—C26	118.6 (3)
O28—Tb1—N31	77.95 (8)	C24—C25—H25	120.7
N21—Tb1—N31	95.15 (8)	C26—C25—H25	120.7
O38—Tb1—N1	81.03 (8)	N21—C26—C25	121.6 (3)
O18—Tb1—N1	78.40 (8)	N21—C26—H26	119.2
O8—Tb1—N1	65.02 (7)	C25—C26—H26	119.2
O28—Tb1—N1	144.00 (7)	O29—C27—O28	124.2 (3)
N21—Tb1—N1	151.31 (8)	O29—C27—C22	120.4 (3)
N31—Tb1—N1	94.19 (8)	O28—C27—C22	115.5 (3)
O38—Tb1—N11	141.19 (7)	C27—O28—Tb1	126.68 (18)
O18—Tb1—N11	65.17 (7)	C27—O29—Na41iii	141.3 (2)
O8—Tb1—N11	78.69 (7)	C23—C30—H30A	109.5
O28—Tb1—N11	80.56 (8)	C23—C30—H30B	109.5
N21—Tb1—N11	88.57 (8)	H30A—C30—H30B	109.5
N31—Tb1—N11	154.06 (8)	C23—C30—H30C	109.5
N1—Tb1—N11	94.71 (8)	H30A—C30—H30C	109.5
C6—N1—C2	118.7 (3)	H30B—C30—H30C	109.5
C6—N1—Tb1	123.9 (2)	C36—N31—C32	119.8 (3)
C2—N1—Tb1	117.35 (19)	C36—N31—Tb1	122.3 (2)
N1—C2—C3	122.5 (3)	C32—N31—Tb1	117.86 (18)
N1—C2—C7	112.8 (3)	N31—C32—C33	122.2 (3)
C3—C2—C7	124.6 (3)	N31—C32—C37	114.0 (2)
C4—C3—C2	116.4 (3)	C33—C32—C37	123.7 (3)
C4—C3—C10	119.4 (3)	C34—C33—C32	116.6 (3)
C2—C3—C10	124.2 (3)	C34—C33—C40	119.6 (3)
C5—C4—C3	121.3 (3)	C32—C33—C40	123.8 (3)
C5—C4—H4	119.3	C35—C34—C33	121.4 (4)
C3—C4—H4	119.3	C35—C34—H34	119.3
C4—C5—C6	118.6 (3)	C33—C34—H34	119.3
C4—C5—H5	120.7	C34—C35—C36	118.3 (3)
C6—C5—H5	120.7	C34—C35—H35	120.9
N1—C6—C5	122.5 (3)	C36—C35—H35	120.9
N1—C6—H6	118.8	N31—C36—C35	121.7 (3)
C5—C6—H6	118.8	N31—C36—H36	119.2
O9—C7—O8	124.5 (3)	C35—C36—H36	119.2
O9—C7—C2	119.6 (3)	O39—C37—O38	124.8 (3)
O8—C7—C2	115.9 (3)	O39—C37—C32	121.1 (3)
C7—O8—Tb1	125.82 (19)	O38—C37—C32	114.1 (3)
C7—O9—Na41	172.7 (2)	C37—O38—Tb1	129.57 (19)
C3—C10—H10A	109.5	C37—O39—Na41iv	124.7 (2)
C3—C10—H10B	109.5	C33—C40—H40A	109.5
H10A—C10—H10B	109.5	C33—C40—H40B	109.5
C3—C10—H10C	109.5	H40A—C40—H40B	109.5
H10A—C10—H10C	109.5	C33—C40—H40C	109.5
H10B—C10—H10C	109.5	H40A—C40—H40C	109.5
C16—N11—C12	119.3 (3)	H40B—C40—H40C	109.5
C16—N11—Tb1	124.5 (2)	O42—Na41—O9	104.30 (10)
C12—N11—Tb1	116.12 (19)	O42—Na41—O39ii	87.81 (9)
N11—C12—C13	122.5 (3)	O9—Na41—O39ii	96.24 (9)
N11—C12—C17	113.6 (3)	O42—Na41—O29i	107.23 (11)
C13—C12—C17	123.9 (3)	O9—Na41—O29i	148.47 (10)
C14—C13—C12	115.4 (3)	O39ii—Na41—O29i	84.99 (9)
C14—C13—C20	120.9 (3)	O42—Na41—O43	102.01 (10)
C12—C13—C20	123.7 (3)	O9—Na41—O43	96.01 (9)
C15—C14—C13	122.5 (4)	O39ii—Na41—O43	161.88 (10)
C15—C14—H14	118.7	O29i—Na41—O43	77.59 (9)
C13—C14—H14	118.7	H42A—O42—H42B	117 (4)
C14—C15—C16	118.3 (3)	H43A—O43—H43B	107 (3)
C14—C15—H15	120.9	H44A—O44—H44B	115 (4)
C16—C15—H15	120.9	C46—C45—H45A	109.5
N11—C16—C15	121.9 (3)	C46—C45—H45B	109.5
N11—C16—H16	119	H45A—C45—H45B	109.5
C15—C16—H16	119	C46—C45—H45C	109.5
O19—C17—O18	124.6 (3)	H45A—C45—H45C	109.5
O19—C17—C12	119.8 (3)	H45B—C45—H45C	109.5
O18—C17—C12	115.5 (3)	O47—C46—C45	113.5 (4)
C17—O18—Tb1	125.3 (2)	O47—C46—H46A	108.9
C13—C20—H20A	109.5	C45—C46—H46A	108.9
C13—C20—H20B	109.5	O47—C46—H46B	108.9
H20A—C20—H20B	109.5	C45—C46—H46B	108.9
C13—C20—H20C	109.5	H46A—C46—H46B	107.7
H20A—C20—H20C	109.5	C46—O47—H47	111 (3)
H20B—C20—H20C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O42—H42A···O47	0.81 (2)	1.95 (2)	2.742 (4)	163 (4)
O42—H42B···O38ii	0.81 (2)	2.01 (2)	2.819 (3)	169 (4)
O43—H43A···O28i	0.82 (2)	1.99 (2)	2.796 (3)	171 (4)
O43—H43A···O29i	0.82 (2)	2.53 (3)	3.050 (3)	122 (3)
O43—H43B···O44i	0.81 (2)	2.02 (2)	2.794 (4)	162 (3)
O44—H44A···O8	0.80 (4)	2.31 (4)	3.103 (4)	170 (4)
O44—H44A···O9	0.80 (4)	2.34 (4)	2.943 (4)	133 (4)
O44—H44B···O43	0.80 (4)	2.07 (4)	2.790 (4)	151 (4)
O47—H47···O19ii	0.80 (2)	1.96 (2)	2.726 (3)	159 (4)

Table 1

Selected bond lengths (Å)

Na41—O9	2.324 (2)
Na41—O29i	2.390 (3)
Na41—O39ii	2.374 (2)
Na41—O42	2.265 (3)
Na41—O43	2.476 (3)

Symmetry codes: (i) ; (ii) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O42—H42A⋯O47	0.81 (2)	1.95 (2)	2.742 (4)	163 (4)
O42—H42B⋯O38ii	0.81 (2)	2.01 (2)	2.819 (3)	169 (4)
O43—H43A⋯O28i	0.82 (2)	1.99 (2)	2.796 (3)	171 (4)
O43—H43A⋯O29i	0.82 (2)	2.53 (3)	3.050 (3)	122 (3)
O43—H43B⋯O44i	0.81 (2)	2.02 (2)	2.794 (4)	162 (3)
O44—H44A⋯O8	0.80 (4)	2.31 (4)	3.103 (4)	170 (4)
O44—H44A⋯O9	0.80 (4)	2.34 (4)	2.943 (4)	133 (4)
O44—H44B⋯O43	0.80 (4)	2.07 (4)	2.790 (4)	151 (4)
O47—H47⋯O19ii	0.80 (2)	1.96 (2)	2.726 (3)	159 (4)

Symmetry codes: (i) ; (ii) .