Poly[[[μ3-5-(pyridine-4-carboxamido)­isophthalato]{μ3-5-[(pyridin-1-ium-4-yl)carbonyl­amino]­isophthalato}­neodymium(III)] dihydrate]

Deng, Y.-F.

doi:10.1107/S1600536811034532

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page m1298

doi:10.1107/S1600536811034532

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Poly[[[μ₃-5-(pyridine-4-carboxamido)isophthalato]{μ₃-5-[(pyridin-1-ium-4-yl)carbonylamino]isophthalato}neodymium(III)] dihydrate]

Yi-Fang Deng ^a ^*

^aDepartment of Chemistry and Materials Science, Hengyang, Hunan 421008, People's Republic of China
^*Correspondence e-mail: yifang7124@163.com

(Received 15 August 2011; accepted 22 August 2011; online 27 August 2011)

In the title compound, {[Nd(C₁₄H₉N₂O₅)(C₁₄H₈N₂O₅)]·2H₂O}_n, the Nd^III atom is eight-coordinated as it is surrounded by eight carboxylate O atoms from six ligands in a distorted square-antiprismatic arrangement. The Nd^III atoms are linked by HL⁻ and L²⁻ ligands [H₂L 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_r = 749.73
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.038
wR(F²) = 0.101
S = 1.07
5287 reflections
406 parameters
H-atom parameters constrained
Δρ_max = 1.83 e Å⁻³
Δρ_min = −1.61 e Å⁻³

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⋯O1^iv	0.85	2.11	2.957 (4)	178
N4—H4A⋯O2W^v	0.86	2.15	2.953 (5)	156
Symmetry codes: (i) $[x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) x-1, y, z; (iii) -x+1, -y+1, -z+1; (iv) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (v) -x+2, -y+1, -z+1.

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811034532/ng5214sup1.cif

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

checkCIF report

Comment top

In recent years, there has a great deal of interest in synthesizing transition metal complexes that exhibit one-, two- and three-dimensional frameworks (Kitagawa & Kondo, 1998). However, high-dimensional lanthanide frameworks are less common (Kiritsis et al., 1998; Zhao et al., 2004). On the other hand, it is well known that carboxylate and pyridine groups have good coordination capacities as well as the amide group, a group with two different types of hydrogen bonding sites: the –NH moiety that acts as an electron acceptor and a –C=O group that acts as an electron donor (Lee, & Kumler, 1962; Huyskens, 1977; Wang et al., 2007). The study reports a new lanthanide(III) coordination polymer, [Nd(HL)(L)]_n.2nH₂O, (I), with H₂L and Nd(NO₃)₃.6H₂O.

In the title compound, the central Nd^III ion is eight-coordinated by eight O atoms from six ligands, which gives a square antiprismatic geometry (Fig. 1). The carboxyl groups of the two unique L^2- (HL^-) ligands exhibit the same coordination modes: there is a monocarboxylate and a dicarboxylate, i.e., the monocarboxylate group coordinates to one Nd^III atom in µ₁-η¹:η¹-chelate mode and the other dicarboxylate connects two Nd^III atoms in a µ₂-η¹:η¹ bridging mode. The pyridyl groups are free. Based on the coordination modes of the carboxylate groups of L^2- (HL^-), a bilayer network is formed (Fig. 2). Adjacent molecules are linked through N—H···O and O—H···O hydrogen bonds into a three-dimensional network.

Related literature top

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 capacities of carboxylate, pyridine and amide groups, see: Huyskens (1977); Lee & Kumler (1962); Wang et al. (2007). Please check expanded text

Experimental top

A mixture of 0.05 mmol Nd(NO₃)₃.6H₂O (21.5 mg. 0.05 mmol), H₂L (28.6 mg, 0.1 mmol), NaOH (6.0 mg, 0.15 mmol), MeOH (4 ml) and H₂O (6 ml) was heated in a 16 ml Teflon-lined reaction vessel at 453 K for 5 days; the mixture was cooled to room temperature over a period of 40 h. The product was collected by filtration, washed with H₂O and air-dried.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The ORTEP drawing of the title compound (I). Displacement ellipsoids are drawn at 30% probability level. [Symmetry codes: (i) 2 - x,-1/2 + y, 3/2 - z (ii) x,1/2 - y, -1/2 + z (iii) 2 - x,-y, 1 - z.]
	Fig. 2. Projection showing the two-dimensional structure of the compound linked by L^2-; all the pyridyl groups are omitted.

Poly[[[µ₃-5-(pyridine-4-carboxamido)isophthalato]{µ₃-5-[(pyridin-1-ium- 4-yl)carbonylamino]isophthalato}neodymium(III)] dihydrate] top

Crystal data top

[Nd(C₁₄H₉N₂O₅)(C₁₄H₈N₂O₅)]·2H₂O	F(000) = 1492
M_r = 749.73	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.055P)² + 3.5595P] where P = (F_o² + 2F_c²)/3
5287 reflections	(Δ/σ)_max < 0.001
406 parameters	Δρ_max = 1.83 e Å⁻³
0 restraints	Δρ_min = −1.61 e Å⁻³

Crystal data top

[Nd(C₁₄H₉N₂O₅)(C₁₄H₈N₂O₅)]·2H₂O	V = 2707.4 (5) Å³
M_r = 749.73	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.4421 (15) Å	µ = 2.00 mm⁻¹
b = 13.7754 (17) Å	T = 291 K
c = 16.2418 (13) Å	0.18 × 0.16 × 0.12 mm
β = 115.813 (4)°

Data collection top

Bruker SMART APEX diffractometer	5287 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	4792 reflections with I > 2σ(I)
T_min = 0.715, T_max = 0.796	R_int = 0.052
14297 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.101	H-atom parameters constrained
S = 1.07	Δρ_max = 1.83 e Å⁻³
5287 reflections	Δρ_min = −1.61 e Å⁻³
406 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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—Nd1^iv	2.371 (3)	C12—H12	0.9300
O4—C8	1.252 (5)	C13—C14	1.372 (6)
O4—Nd1^v	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—Nd1^iv	2.508 (3)	C17—H17	0.9300
O9—C22	1.258 (5)	C18—C19	1.397 (6)
O9—Nd1^iv	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—Nd1^iv	172.9 (3)	C20—C19—H19	119.8
C8—O4—Nd1^v	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—Nd1^iv	93.0 (2)	C21—C20—C22	119.7 (3)
C22—O9—Nd1^iv	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—Nd1^iv	60.3 (2)
C23—N4—C18	127.4 (4)	O8—C22—Nd1^iv	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)	Nd1^iv—O9—C22—O8	4.0 (4)
C2—C3—C4—C5	−0.8 (6)	Nd1^iv—O9—C22—C20	−175.0 (3)
C2—C3—C4—C8	176.1 (4)	Nd1^iv—O8—C22—O9	−4.0 (4)
C3—C4—C5—C6	−1.5 (6)	Nd1^iv—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)
Nd1^v—O4—C8—O3	−22.1 (5)	N4—C23—C24—C25	−176.3 (4)
Nd1^v—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)

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

Hydrogen-bond geometry (Å, º) top

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···O2^vi	0.89	1.85	2.725 (4)	171
O1W—H1WA···O9^vi	0.85	1.89	2.734 (5)	177
O2W—H2WA···O10^vi	0.85	2.52	3.124 (5)	129
O1W—H1WB···O10^vii	0.85	2.00	2.845 (5)	171
O2W—H2WA···O4^viii	0.85	2.36	2.923 (5)	125
O2W—H2WB···O1^ix	0.85	2.11	2.957 (4)	178
N4—H4A···O2W^x	0.86	2.15	2.953 (5)	156

Symmetry codes: (vi) x−1, −y+1/2, z−1/2; (vii) x−1, y, z; (viii) −x+1, −y+1, −z+1; (ix) −x+1, y+1/2, −z+1/2; (x) −x+2, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Nd(C₁₄H₉N₂O₅)(C₁₄H₈N₂O₅)]·2H₂O
M_r	749.73
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	291
a, b, c (Å)	13.4421 (15), 13.7754 (17), 16.2418 (13)
β (°)	115.813 (4)
V (Å³)	2707.4 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.00
Crystal size (mm)	0.18 × 0.16 × 0.12

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2008)
T_min, T_max	0.715, 0.796
No. of measured, independent and observed [I > 2σ(I)] reflections	14297, 5287, 4792
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.101, 1.07
No. of reflections	5287
No. of parameters	406
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.83, −1.61

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1W	0.86	2.06	2.846 (5)	151.3
N1—H1···O2ⁱ	0.89	1.85	2.725 (4)	170.8
O1W—H1WA···O9ⁱ	0.85	1.89	2.734 (5)	176.8
O2W—H2WA···O10ⁱ	0.85	2.52	3.124 (5)	129.3
O1W—H1WB···O10ⁱⁱ	0.85	2.00	2.845 (5)	171.1
O2W—H2WA···O4ⁱⁱⁱ	0.85	2.36	2.923 (5)	124.6
O2W—H2WB···O1^iv	0.85	2.11	2.957 (4)	177.9
N4—H4A···O2W^v	0.86	2.15	2.953 (5)	155.6

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

Acknowledgements

This work was supported by Hengyang Bureau of Science and Technology (grant No. 2009 K J29).

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