Poly[[[μ(3)-5-(pyridine-4-carboxamido)-isophthalato]{μ(3)-5-[(pyridin-1-ium-4-yl)carbonyl-amino]-isophthalato}-neodymium(III)] dihydrate].

In the title compound, {[Nd(C(14)H(9)N(2)O(5))(C(14)H(8)N(2)O(5))]·2H(2)O}(n), the Nd(III) atom is eight-coordinated as it is surrounded by eight carboxyl-ate O atoms from six ligands in a distorted square-anti-prismatic arrangement. The Nd(III) atoms are linked by HL(-) and L(2-) ligands [H(2)L is 5-(pyridine-4-carboxamido)-isophthalic acid], forming a bilayer network. The layers are linked into a three-demensional network through N-H⋯O and O-H⋯O hydrogen bonds.

Related literature

For background on transition metal complexes that exhibit one-, two- and three-dimensional frameworks, see: Kitagawa & Kondo (1998 ▶). For high-dimensional lanthanide frameworks, see: Kiritsis et al. (1998 ▶); Zhao et al. (2004 ▶). For coordination capabilities of carboxyl­ate, pyridine and amide groups, see: Huyskens (1977 ▶); Lee & Kumler (1962 ▶); Wang et al. (2007 ▶).

Experimental

Crystal data

[Nd(C14H9N2O5)(C14H8N2O5)]·2H2O

M = 749.73

Monoclinic,

a = 13.4421 (15) Å

b = 13.7754 (17) Å

c = 16.2418 (13) Å

β = 115.813 (4)°

V = 2707.4 (5) Å3

Z = 4

Mo Kα radiation

μ = 2.00 mm−1

T = 291 K

0.18 × 0.16 × 0.12 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008 ▶) T min = 0.715, T max = 0.796

14297 measured reflections

5287 independent reflections

4792 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.101

S = 1.07

5287 reflections

406 parameters

H-atom parameters constrained

Δρmax = 1.83 e Å−3

Δρmin = −1.61 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; 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: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811034532/ng5214sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811034532/ng5214Isup2.hkl

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

[Nd(C14H9N2O5)(C14H8N2O5)]·2H2O	F(000) = 1492
Mr = 749.73	Dx = 1.839 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -p 2ybc	Cell parameters from 8058 reflections
a = 13.4421 (15) Å	θ = 2.2–28.3°
b = 13.7754 (17) Å	µ = 2.00 mm−1
c = 16.2418 (13) Å	T = 291 K
β = 115.813 (4)°	Block, colorless
V = 2707.4 (5) Å3	0.18 × 0.16 × 0.12 mm
Z = 4

Bruker SMART APEX diffractometer	5287 independent reflections
Radiation source: fine-focus sealed tube	4792 reflections with I > 2σ(I)
graphite	Rint = 0.052
φ and ω scans	θmax = 26.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	h = −16→15
Tmin = 0.715, Tmax = 0.796	k = −16→16
14297 measured reflections	l = −20→16

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.055P)2 + 3.5595P] where P = (Fo2 + 2Fc2)/3
5287 reflections	(Δ/σ)max < 0.001
406 parameters	Δρmax = 1.83 e Å−3
0 restraints	Δρmin = −1.61 e Å−3

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
O2W	0.4403 (3)	0.6060 (3)	0.0967 (3)	0.0456 (9)
O1W	0.4253 (3)	0.1460 (3)	0.5360 (2)	0.0537 (11)
Nd1	0.898403 (16)	0.014994 (16)	0.571291 (14)	0.01719 (10)
O1	0.7704 (2)	0.1428 (2)	0.56596 (19)	0.0250 (6)
O2	0.9065 (2)	0.1322 (2)	0.70371 (19)	0.0236 (6)
O3	0.9144 (2)	0.4679 (2)	0.8775 (2)	0.0289 (7)
O4	0.7730 (2)	0.4510 (2)	0.91087 (18)	0.0244 (6)
O5	0.4645 (3)	0.5086 (2)	0.5783 (2)	0.0356 (8)
O6	0.9932 (2)	0.1532 (2)	0.55514 (19)	0.0212 (6)
O7	1.1226 (2)	0.1364 (2)	0.50548 (19)	0.0218 (6)
O8	1.0730 (2)	0.4069 (2)	0.7959 (2)	0.0279 (7)
O9	1.2447 (2)	0.4326 (2)	0.89481 (19)	0.0255 (7)
O10	1.4746 (3)	0.0803 (2)	0.7157 (2)	0.0374 (8)
N2	0.4776 (3)	0.3440 (3)	0.5862 (2)	0.0256 (8)
H2	0.4395	0.2915	0.5689	0.031*
N1	0.0898 (3)	0.4082 (3)	0.3610 (3)	0.0343 (9)
H1	0.0259	0.3971	0.3130	0.041*
N4	1.4748 (3)	0.2155 (3)	0.7943 (2)	0.0275 (8)
H4A	1.5175	0.2570	0.8333	0.033*
N3	1.8768 (3)	0.1047 (4)	0.9233 (4)	0.0524 (13)
C1	0.8171 (3)	0.1699 (3)	0.6476 (3)	0.0189 (8)
C2	0.7617 (3)	0.2495 (3)	0.6762 (3)	0.0174 (8)
C3	0.8178 (3)	0.3080 (3)	0.7518 (3)	0.0177 (8)
H3	0.8933	0.3002	0.7871	0.021*
C4	0.7597 (3)	0.3787 (3)	0.7744 (2)	0.0163 (8)
C5	0.6465 (3)	0.3920 (3)	0.7214 (3)	0.0202 (8)
H5	0.6080	0.4383	0.7377	0.024*
C6	0.5922 (3)	0.3350 (3)	0.6440 (3)	0.0197 (8)
C7	0.6500 (3)	0.2648 (3)	0.6220 (3)	0.0218 (8)
H7	0.6133	0.2270	0.5700	0.026*
C8	0.8192 (3)	0.4374 (3)	0.8595 (3)	0.0165 (8)
C9	0.4240 (3)	0.4284 (3)	0.5564 (3)	0.0240 (9)
C10	0.3035 (3)	0.4177 (3)	0.4879 (3)	0.0229 (9)
C11	0.2528 (4)	0.4968 (4)	0.4336 (4)	0.0423 (13)
H11	0.2917	0.5545	0.4407	0.051*
C12	0.1446 (5)	0.4904 (4)	0.3688 (4)	0.0490 (15)
H12	0.1105	0.5430	0.3312	0.059*
C13	0.1334 (4)	0.3328 (4)	0.4145 (4)	0.0414 (12)
H13	0.0912	0.2773	0.4082	0.050*
C14	0.2411 (4)	0.3362 (4)	0.4796 (3)	0.0383 (12)
H14	0.2717	0.2834	0.5180	0.046*
C15	1.0895 (3)	0.1640 (3)	0.5638 (3)	0.0178 (8)
C16	1.1716 (3)	0.2123 (3)	0.6484 (3)	0.0195 (8)
C17	1.2835 (3)	0.1920 (3)	0.6786 (3)	0.0222 (9)
H17	1.3067	0.1502	0.6455	0.027*
C18	1.3594 (3)	0.2342 (3)	0.7580 (3)	0.0254 (9)
C19	1.3240 (3)	0.2999 (3)	0.8052 (3)	0.0248 (9)
H19	1.3756	0.3302	0.8576	0.030*
C20	1.2126 (3)	0.3201 (3)	0.7746 (3)	0.0197 (8)
C21	1.1354 (3)	0.2748 (3)	0.6964 (3)	0.0212 (8)
H21	1.0603	0.2863	0.6766	0.025*
C22	1.1748 (3)	0.3909 (3)	0.8245 (3)	0.0195 (8)
C23	1.5245 (3)	0.1407 (3)	0.7749 (3)	0.0260 (9)
C24	1.6479 (3)	0.1320 (3)	0.8288 (3)	0.0244 (9)
C25	1.7001 (4)	0.0579 (4)	0.8048 (4)	0.0432 (13)
H25	1.6603	0.0165	0.7563	0.052*
C26	1.8130 (4)	0.0472 (5)	0.8552 (4)	0.0518 (15)
H26	1.8468	−0.0042	0.8402	0.062*
C27	1.8250 (4)	0.1743 (4)	0.9450 (4)	0.0453 (13)
H27	1.8669	0.2148	0.9935	0.054*
C28	1.7122 (4)	0.1909 (4)	0.9002 (3)	0.0362 (11)
H28	1.6804	0.2415	0.9183	0.043*
H1WA	0.3687	0.1203	0.4936	0.054*
H1WB	0.4382	0.1202	0.5872	0.054*
H2WA	0.4156	0.5777	0.1305	0.054*
H2WB	0.3799	0.6182	0.0501	0.054*

	U11	U22	U33	U12	U13	U23
O2W	0.0282 (18)	0.050 (2)	0.050 (2)	0.0082 (17)	0.0092 (16)	0.0003 (19)
O1W	0.056 (2)	0.050 (2)	0.033 (2)	0.025 (2)	−0.0012 (18)	0.0001 (18)
Nd1	0.01348 (13)	0.02044 (15)	0.01550 (14)	0.00045 (7)	0.00432 (10)	0.00084 (8)
O1	0.0206 (14)	0.0288 (16)	0.0190 (14)	0.0067 (12)	0.0026 (12)	−0.0077 (12)
O2	0.0143 (14)	0.0323 (16)	0.0176 (14)	0.0070 (12)	0.0008 (12)	−0.0019 (12)
O3	0.0126 (14)	0.0271 (16)	0.0389 (18)	−0.0022 (12)	0.0037 (13)	−0.0093 (14)
O4	0.0250 (15)	0.0305 (16)	0.0154 (14)	−0.0016 (13)	0.0067 (12)	−0.0050 (12)
O5	0.0210 (17)	0.0343 (19)	0.036 (2)	−0.0009 (13)	−0.0023 (15)	−0.0072 (15)
O6	0.0143 (13)	0.0190 (14)	0.0285 (15)	−0.0013 (11)	0.0076 (12)	−0.0004 (12)
O7	0.0225 (14)	0.0219 (15)	0.0213 (14)	−0.0033 (12)	0.0098 (12)	−0.0039 (12)
O8	0.0141 (14)	0.0380 (18)	0.0269 (16)	0.0020 (13)	0.0046 (12)	−0.0134 (14)
O9	0.0177 (14)	0.0329 (17)	0.0211 (15)	0.0025 (12)	0.0040 (12)	−0.0097 (13)
O10	0.0294 (17)	0.0375 (19)	0.0365 (19)	0.0018 (15)	0.0063 (15)	−0.0118 (16)
N2	0.0120 (16)	0.0273 (19)	0.0258 (19)	−0.0004 (14)	−0.0027 (14)	−0.0088 (15)
N1	0.0175 (18)	0.048 (2)	0.025 (2)	−0.0038 (17)	−0.0017 (16)	0.0043 (18)
N4	0.0122 (16)	0.037 (2)	0.030 (2)	0.0002 (15)	0.0056 (15)	−0.0132 (17)
N3	0.026 (2)	0.051 (3)	0.073 (3)	0.005 (2)	0.015 (2)	−0.008 (3)
C1	0.0180 (19)	0.0190 (19)	0.021 (2)	−0.0013 (16)	0.0092 (17)	−0.0008 (16)
C2	0.0137 (18)	0.0183 (19)	0.0177 (19)	0.0018 (15)	0.0046 (16)	−0.0015 (15)
C3	0.0101 (17)	0.023 (2)	0.0165 (19)	0.0022 (15)	0.0027 (15)	0.0013 (16)
C4	0.0112 (17)	0.0204 (19)	0.0127 (18)	−0.0007 (15)	0.0008 (15)	−0.0021 (15)
C5	0.0152 (19)	0.022 (2)	0.020 (2)	0.0030 (15)	0.0046 (16)	−0.0050 (16)
C6	0.0102 (17)	0.025 (2)	0.0173 (19)	−0.0010 (15)	−0.0002 (15)	−0.0052 (16)
C7	0.0166 (19)	0.025 (2)	0.018 (2)	−0.0007 (16)	0.0023 (16)	−0.0054 (17)
C8	0.0125 (18)	0.0145 (19)	0.0145 (18)	0.0009 (14)	−0.0016 (15)	0.0003 (15)
C9	0.0144 (19)	0.037 (3)	0.017 (2)	0.0015 (18)	0.0030 (16)	−0.0061 (18)
C10	0.0167 (19)	0.031 (2)	0.0173 (19)	0.0016 (17)	0.0040 (16)	−0.0023 (17)
C11	0.026 (3)	0.042 (3)	0.044 (3)	−0.005 (2)	0.002 (2)	0.012 (2)
C12	0.029 (3)	0.056 (4)	0.044 (3)	−0.002 (2)	−0.001 (3)	0.022 (3)
C13	0.023 (2)	0.038 (3)	0.050 (3)	−0.004 (2)	0.003 (2)	0.007 (2)
C14	0.021 (2)	0.040 (3)	0.042 (3)	0.003 (2)	0.002 (2)	0.011 (2)
C15	0.0171 (19)	0.0111 (18)	0.022 (2)	−0.0002 (14)	0.0056 (16)	0.0025 (15)
C16	0.0175 (19)	0.024 (2)	0.0174 (19)	−0.0035 (16)	0.0081 (16)	−0.0018 (16)
C17	0.0186 (19)	0.025 (2)	0.023 (2)	−0.0008 (16)	0.0091 (17)	−0.0073 (17)
C18	0.016 (2)	0.033 (2)	0.025 (2)	0.0006 (17)	0.0076 (17)	−0.0049 (19)
C19	0.018 (2)	0.032 (2)	0.022 (2)	−0.0007 (17)	0.0065 (17)	−0.0077 (18)
C20	0.0191 (19)	0.023 (2)	0.0185 (19)	0.0010 (16)	0.0098 (16)	−0.0014 (16)
C21	0.0139 (18)	0.025 (2)	0.025 (2)	−0.0012 (16)	0.0094 (17)	−0.0026 (17)
C22	0.019 (2)	0.020 (2)	0.021 (2)	−0.0006 (16)	0.0104 (17)	−0.0002 (16)
C23	0.023 (2)	0.029 (2)	0.025 (2)	−0.0020 (18)	0.0097 (19)	−0.0018 (18)
C24	0.017 (2)	0.027 (2)	0.030 (2)	0.0005 (17)	0.0117 (18)	0.0009 (18)
C25	0.032 (3)	0.047 (3)	0.049 (3)	0.002 (2)	0.016 (2)	−0.014 (3)
C26	0.029 (3)	0.055 (3)	0.071 (4)	0.010 (3)	0.021 (3)	−0.018 (3)
C27	0.026 (2)	0.041 (3)	0.055 (3)	−0.003 (2)	0.005 (2)	−0.013 (3)
C28	0.024 (2)	0.033 (3)	0.048 (3)	0.004 (2)	0.013 (2)	−0.009 (2)

O2W—H2WA	0.8499	C2—C3	1.385 (5)
O2W—H2WB	0.8515	C2—C7	1.386 (5)
O1W—H1WA	0.8498	C3—C4	1.393 (5)
O1W—H1WB	0.8499	C3—H3	0.9300
Nd1—O6	2.368 (3)	C4—C5	1.395 (5)
Nd1—O3i	2.371 (3)	C4—C8	1.498 (5)
Nd1—O7ii	2.383 (3)	C5—C6	1.390 (5)
Nd1—O1	2.436 (3)	C5—H5	0.9300
Nd1—O4iii	2.455 (3)	C6—C7	1.381 (5)
Nd1—O9i	2.493 (3)	C7—H7	0.9300
Nd1—O8i	2.508 (3)	C9—C10	1.521 (5)
Nd1—O2	2.653 (3)	C10—C14	1.373 (6)
O1—C1	1.252 (5)	C10—C11	1.381 (7)
O2—C1	1.261 (5)	C11—C12	1.377 (8)
O3—C8	1.254 (5)	C11—H11	0.9300
O3—Nd1iv	2.371 (3)	C12—H12	0.9300
O4—C8	1.252 (5)	C13—C14	1.372 (6)
O4—Nd1v	2.455 (3)	C13—H13	0.9300
O5—C9	1.214 (5)	C14—H14	0.9300
O6—C15	1.249 (4)	C15—C16	1.493 (5)
O7—C15	1.267 (5)	C16—C21	1.384 (5)
O7—Nd1ii	2.383 (3)	C16—C17	1.392 (5)
O8—C22	1.259 (5)	C17—C18	1.376 (6)
O8—Nd1iv	2.508 (3)	C17—H17	0.9300
O9—C22	1.258 (5)	C18—C19	1.397 (6)
O9—Nd1iv	2.493 (3)	C19—C20	1.386 (5)
O10—C23	1.226 (5)	C19—H19	0.9300
N2—C9	1.343 (6)	C20—C21	1.389 (6)
N2—C6	1.418 (5)	C20—C22	1.492 (5)
N2—H2	0.8596	C21—H21	0.9300
N1—C13	1.317 (6)	C23—C24	1.505 (6)
N1—C12	1.327 (7)	C24—C28	1.370 (6)
N1—H1	0.8864	C24—C25	1.387 (6)
N4—C23	1.339 (5)	C25—C26	1.383 (7)
N4—C18	1.422 (5)	C25—H25	0.9300
N4—H4A	0.8607	C26—H26	0.9300
N3—C27	1.319 (7)	C27—C28	1.386 (6)
N3—C26	1.326 (7)	C27—H27	0.9300
C1—C2	1.509 (5)	C28—H28	0.9300
H2WA—O2W—H2WB	100.1	C7—C6—C5	119.7 (3)
H1WA—O1W—H1WB	110.4	C7—C6—N2	117.5 (3)
O6—Nd1—O3i	73.66 (10)	C5—C6—N2	122.7 (4)
O6—Nd1—O7ii	126.34 (9)	C6—C7—C2	121.2 (4)
O3i—Nd1—O7ii	79.05 (10)	C6—C7—H7	119.4
O6—Nd1—O1	79.68 (10)	C2—C7—H7	119.4
O3i—Nd1—O1	146.63 (10)	O4—C8—O3	123.2 (4)
O7ii—Nd1—O1	133.86 (9)	O4—C8—C4	118.4 (3)
O6—Nd1—O4iii	83.28 (10)	O3—C8—C4	118.4 (3)
O3i—Nd1—O4iii	123.93 (10)	O5—C9—N2	125.5 (4)
O7ii—Nd1—O4iii	75.02 (10)	O5—C9—C10	120.1 (4)
O1—Nd1—O4iii	71.12 (10)	N2—C9—C10	114.4 (4)
O6—Nd1—O9i	153.47 (10)	C14—C10—C11	118.2 (4)
O3i—Nd1—O9i	126.94 (10)	C14—C10—C9	124.2 (4)
O7ii—Nd1—O9i	77.88 (10)	C11—C10—C9	117.6 (4)
O1—Nd1—O9i	74.69 (10)	C12—C11—C10	120.1 (5)
O4iii—Nd1—O9i	94.70 (9)	C12—C11—H11	120.0
O6—Nd1—O8i	133.14 (10)	C10—C11—H11	120.0
O3i—Nd1—O8i	78.10 (10)	N1—C12—C11	119.0 (5)
O7ii—Nd1—O8i	82.49 (10)	N1—C12—H12	120.5
O1—Nd1—O8i	107.52 (10)	C11—C12—H12	120.5
O4iii—Nd1—O8i	143.44 (10)	N1—C13—C14	119.9 (5)
O9i—Nd1—O8i	51.99 (9)	N1—C13—H13	120.1
O6—Nd1—O2	76.49 (9)	C14—C13—H13	120.1
O3i—Nd1—O2	102.66 (10)	C13—C14—C10	119.9 (5)
O7ii—Nd1—O2	155.57 (9)	C13—C14—H14	120.1
O1—Nd1—O2	50.83 (9)	C10—C14—H14	120.1
O4iii—Nd1—O2	120.74 (9)	O6—C15—O7	124.3 (4)
O9i—Nd1—O2	82.03 (10)	O6—C15—C16	118.1 (3)
O8i—Nd1—O2	74.19 (11)	O7—C15—C16	117.6 (3)
O6—Nd1—C22i	152.25 (11)	C21—C16—C17	121.2 (4)
O3i—Nd1—C22i	102.40 (11)	C21—C16—C15	119.7 (3)
O7ii—Nd1—C22i	78.11 (10)	C17—C16—C15	119.1 (3)
O1—Nd1—C22i	91.90 (11)	C18—C17—C16	119.5 (4)
O4iii—Nd1—C22i	119.15 (10)	C18—C17—H17	120.3
O9i—Nd1—C22i	25.98 (10)	C16—C17—H17	120.3
O8i—Nd1—C22i	26.04 (10)	C17—C18—C19	119.8 (4)
O2—Nd1—C22i	77.73 (10)	C17—C18—N4	122.8 (4)
C1—O1—Nd1	99.1 (2)	C19—C18—N4	117.4 (4)
C1—O2—Nd1	88.6 (2)	C20—C19—C18	120.4 (4)
C8—O3—Nd1iv	172.9 (3)	C20—C19—H19	119.8
C8—O4—Nd1v	115.1 (2)	C18—C19—H19	119.8
C15—O6—Nd1	131.7 (2)	C19—C20—C21	119.9 (4)
C15—O7—Nd1ii	130.8 (2)	C19—C20—C22	120.4 (4)
C22—O8—Nd1iv	93.0 (2)	C21—C20—C22	119.7 (3)
C22—O9—Nd1iv	93.8 (2)	C16—C21—C20	119.2 (4)
C9—N2—C6	124.9 (4)	C16—C21—H21	120.4
C9—N2—H2	117.5	C20—C21—H21	120.4
C6—N2—H2	117.6	O9—C22—O8	121.1 (4)
C13—N1—C12	122.8 (4)	O9—C22—C20	119.7 (3)
C13—N1—H1	115.2	O8—C22—C20	119.1 (4)
C12—N1—H1	121.1	O9—C22—Nd1iv	60.3 (2)
C23—N4—C18	127.4 (4)	O8—C22—Nd1iv	61.0 (2)
C23—N4—H4A	116.3	O10—C23—N4	123.2 (4)
C18—N4—H4A	116.3	O10—C23—C24	119.3 (4)
C27—N3—C26	115.5 (4)	N4—C23—C24	117.4 (4)
O1—C1—O2	121.5 (4)	C28—C24—C25	117.6 (4)
O1—C1—C2	117.1 (3)	C28—C24—C23	125.0 (4)
O2—C1—C2	121.3 (3)	C25—C24—C23	117.3 (4)
C3—C2—C7	119.7 (4)	C26—C25—C24	118.1 (5)
C3—C2—C1	123.0 (3)	C26—C25—H25	121.0
C7—C2—C1	117.3 (3)	C24—C25—H25	121.0
C2—C3—C4	119.2 (3)	N3—C26—C25	125.1 (5)
C2—C3—H3	120.4	N3—C26—H26	117.5
C4—C3—H3	120.4	C25—C26—H26	117.5
C3—C4—C5	121.0 (3)	N3—C27—C28	124.4 (5)
C3—C4—C8	119.0 (3)	N3—C27—H27	117.8
C5—C4—C8	119.9 (3)	C28—C27—H27	117.8
C6—C5—C4	119.1 (4)	C24—C28—C27	119.3 (4)
C6—C5—H5	120.5	C24—C28—H28	120.4
C4—C5—H5	120.5	C27—C28—H28	120.4
O6—Nd1—O1—C1	−81.7 (2)	N2—C9—C10—C14	22.5 (6)
O3i—Nd1—O1—C1	−44.5 (3)	O5—C9—C10—C11	18.0 (6)
O7ii—Nd1—O1—C1	146.9 (2)	N2—C9—C10—C11	−160.5 (5)
O4iii—Nd1—O1—C1	−168.1 (3)	C14—C10—C11—C12	−4.3 (9)
O9i—Nd1—O1—C1	91.3 (3)	C9—C10—C11—C12	178.4 (5)
O8i—Nd1—O1—C1	50.4 (3)	C13—N1—C12—C11	2.1 (9)
O2—Nd1—O1—C1	−0.8 (2)	C10—C11—C12—N1	1.3 (10)
C22i—Nd1—O1—C1	71.7 (3)	C12—N1—C13—C14	−2.4 (9)
O6—Nd1—O2—C1	88.4 (2)	N1—C13—C14—C10	−0.8 (8)
O3i—Nd1—O2—C1	157.9 (2)	C11—C10—C14—C13	4.1 (8)
O7ii—Nd1—O2—C1	−110.8 (3)	C9—C10—C14—C13	−178.9 (5)
O1—Nd1—O2—C1	0.8 (2)	Nd1—O6—C15—O7	75.6 (5)
O4iii—Nd1—O2—C1	14.8 (3)	Nd1—O6—C15—C16	−104.1 (4)
O9i—Nd1—O2—C1	−75.9 (2)	Nd1ii—O7—C15—O6	−48.7 (5)
O8i—Nd1—O2—C1	−128.6 (2)	Nd1ii—O7—C15—C16	131.1 (3)
C22i—Nd1—O2—C1	−102.0 (2)	O6—C15—C16—C21	−24.5 (5)
O3i—Nd1—O6—C15	8.1 (3)	O7—C15—C16—C21	155.8 (4)
O7ii—Nd1—O6—C15	−54.4 (4)	O6—C15—C16—C17	154.2 (4)
O1—Nd1—O6—C15	167.8 (4)	O7—C15—C16—C17	−25.5 (5)
O4iii—Nd1—O6—C15	−120.2 (3)	C21—C16—C17—C18	0.4 (6)
O9i—Nd1—O6—C15	152.7 (3)	C15—C16—C17—C18	−178.3 (4)
O8i—Nd1—O6—C15	63.4 (4)	C16—C17—C18—C19	−2.6 (7)
O2—Nd1—O6—C15	115.9 (3)	C16—C17—C18—N4	178.6 (4)
C22i—Nd1—O6—C15	93.7 (4)	C23—N4—C18—C17	−18.5 (7)
Nd1—O1—C1—O2	1.5 (4)	C23—N4—C18—C19	162.6 (4)
Nd1—O1—C1—C2	−178.3 (3)	C17—C18—C19—C20	2.4 (7)
Nd1—O2—C1—O1	−1.4 (4)	N4—C18—C19—C20	−178.8 (4)
Nd1—O2—C1—C2	178.5 (3)	C18—C19—C20—C21	0.1 (7)
O1—C1—C2—C3	−158.1 (4)	C18—C19—C20—C22	−179.4 (4)
O2—C1—C2—C3	22.1 (6)	C17—C16—C21—C20	2.0 (6)
O1—C1—C2—C7	20.5 (5)	C15—C16—C21—C20	−179.3 (4)
O2—C1—C2—C7	−159.4 (4)	C19—C20—C21—C16	−2.2 (6)
C7—C2—C3—C4	2.7 (6)	C22—C20—C21—C16	177.3 (4)
C1—C2—C3—C4	−178.8 (4)	Nd1iv—O9—C22—O8	4.0 (4)
C2—C3—C4—C5	−0.8 (6)	Nd1iv—O9—C22—C20	−175.0 (3)
C2—C3—C4—C8	176.1 (4)	Nd1iv—O8—C22—O9	−4.0 (4)
C3—C4—C5—C6	−1.5 (6)	Nd1iv—O8—C22—C20	175.1 (3)
C8—C4—C5—C6	−178.3 (4)	C19—C20—C22—O9	0.1 (6)
C4—C5—C6—C7	1.7 (6)	C21—C20—C22—O9	−179.4 (4)
C4—C5—C6—N2	−179.8 (4)	C19—C20—C22—O8	−179.0 (4)
C9—N2—C6—C7	−136.0 (4)	C21—C20—C22—O8	1.5 (6)
C9—N2—C6—C5	45.4 (6)	C18—N4—C23—O10	5.7 (7)
C5—C6—C7—C2	0.3 (6)	C18—N4—C23—C24	−174.7 (4)
N2—C6—C7—C2	−178.3 (4)	O10—C23—C24—C28	−175.8 (5)
C3—C2—C7—C6	−2.5 (6)	N4—C23—C24—C28	4.6 (7)
C1—C2—C7—C6	178.9 (4)	O10—C23—C24—C25	3.3 (6)
Nd1v—O4—C8—O3	−22.1 (5)	N4—C23—C24—C25	−176.3 (4)
Nd1v—O4—C8—C4	155.6 (3)	C28—C24—C25—C26	0.9 (8)
C3—C4—C8—O4	−135.3 (4)	C23—C24—C25—C26	−178.3 (5)
C5—C4—C8—O4	41.6 (5)	C27—N3—C26—C25	2.8 (10)
C3—C4—C8—O3	42.5 (5)	C24—C25—C26—N3	−2.4 (10)
C5—C4—C8—O3	−140.6 (4)	C26—N3—C27—C28	−1.8 (9)
C6—N2—C9—O5	−4.0 (7)	C25—C24—C28—C27	−0.1 (7)
C6—N2—C9—C10	174.4 (4)	C23—C24—C28—C27	179.1 (5)
O5—C9—C10—C14	−159.0 (5)	N3—C27—C28—C24	0.5 (9)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1W	0.86	2.06	2.846 (5)	151.
N1—H1···O2vi	0.89	1.85	2.725 (4)	171.
O1W—H1WA···O9vi	0.85	1.89	2.734 (5)	177.
O2W—H2WA···O10vi	0.85	2.52	3.124 (5)	129.
O1W—H1WB···O10vii	0.85	2.00	2.845 (5)	171.
O2W—H2WA···O4viii	0.85	2.36	2.923 (5)	125.
O2W—H2WB···O1ix	0.85	2.11	2.957 (4)	178.
N4—H4A···O2Wx	0.86	2.15	2.953 (5)	156.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1W	0.86	2.06	2.846 (5)	151
N1—H1⋯O2i	0.89	1.85	2.725 (4)	171
O1W—H1WA⋯O9i	0.85	1.89	2.734 (5)	177
O2W—H2WA⋯O10i	0.85	2.52	3.124 (5)	129
O1W—H1WB⋯O10ii	0.85	2.00	2.845 (5)	171
O2W—H2WA⋯O4iii	0.85	2.36	2.923 (5)	125
O2W—H2WB⋯O1iv	0.85	2.11	2.957 (4)	178
N4—H4A⋯O2Wv	0.86	2.15	2.953 (5)	156

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