Tetra­kis(nitrato-κ2O,O′)[N,N′-1,4-phenyl­enebis(pyridine-4-carboxamide)-κN1](4-{[4-(pyridine-4-carboxamido-κN1)phen­yl]carbamo­yl}pyridin-1-ium)neodymium(III)

Zhang, Y.; Hao, J.-J.; Zhou, H.

doi:10.1107/S1600536812011397

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Page m459

doi:10.1107/S1600536812011397

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Tetrakis(nitrato-κ²O,O′)[N,N′-1,4-phenylenebis(pyridine-4-carboxamide)-κN¹](4-{[4-(pyridine-4-carboxamido-κN¹)phenyl]carbamoyl}pyridin-1-ium)neodymium(III)

Yun Zhang,^a Jiao-Jiao Hao ^a and Hu Zhou ^a ^*

^aSchool of Material Science and Engineering, Jiangsu University of Science and Technology, Zhenjiang 212003, People's Republic of China
^*Correspondence e-mail: aihuayuan@163.com

(Received 14 March 2012; accepted 15 March 2012; online 21 March 2012)

In the title compound, [Nd(NO₃)₄(C₁₈H₁₅N₄O₂)(C₁₈H₁₄N₄O₂)], the Nd^III centre is located on a twofold axis and exhibits a ten-coordinated distorted bicapped square-antiprismatic geometry. The pyridinium NH H atom is disordered over the two ligands. Adjacent mononuclear clusters are linked through N—H⋯O and N—H⋯N hydrogen-bonding interactions, generating layers in the (102) plane.

Related literature

For general background to octacyanometallate-based compounds, see: Sieklucka et al. (2011 ); Zhou et al. (2010 ); Bok et al. (1975 ). For background to N,N′-bis(4-pyridylformamide)-1,4-benzene, see: Niu et al. (2004 ); Pansanel et al. (2006 ); Song et al. (2009 ).

Experimental

Crystal data

[Nd(NO₃)₄(C₁₈H₁₅N₄O₂)(C₁₈H₁₄N₄O₂)]
M_r = 1029.95
Monoclinic, C 2/c
a = 19.856 (4) Å
b = 7.8491 (14) Å
c = 25.338 (5) Å
β = 95.153 (2)°
V = 3933.0 (13) Å³
Z = 4
Mo Kα radiation
μ = 1.41 mm⁻¹
T = 291 K
0.28 × 0.24 × 0.22 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.693, T_max = 0.746
14547 measured reflections
3853 independent reflections
3510 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.070
S = 0.99
3853 reflections
294 parameters
H-atom parameters constrained
Δρ_max = 1.29 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4A⋯O1ⁱ	0.89	2.43	3.285 (4)	160
N5—H5A⋯O7ⁱ	0.89	2.23	2.966 (4)	140
N6—H6⋯N6ⁱⁱ	0.89	1.86	2.742 (5)	168
Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y+4, -z.

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812011397/bt5847sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812011397/bt5847Isup2.hkl

checkCIF report

Comment top

In the past few years, octacyanide-bearing precursors [M(CN)₈]^3/4- (M = Mo, W) are frequently utilized in the construction of various dimensional structures, and the resulting materials have displayed rich magnetic properties (Sieklucka et al., 2011). However, the [M(CN)₈]^3/4--based lanthanide assemblies are relatively limited and poorly investigated, because of the liability of the lanthanide centers, the rather large anisotropic magnetic moments, and the absence of design strategies for the 4f-4 d/5 d system (Zhou et al., 2010). Recently, we have used [Mo(CN)₈]^3- as building block to react with Nd³⁺ and pillar ligand N,N'-bis(4-pyridylformamide)-1,4-benzene, in order to construct high-dimensional bimetallic assemblies. Unexpectedly, a new mononuclear culster, Nd(H_0.5((N,N'-bis(4-pyridylformamide)-1,4-benzene))₂(NO₃)₄, has been obtained. In the structure, the Nd^III ion is ten-coordinated by eight oxygen atoms of four NO₃^- anions and two nitrogen atoms of two N,N'-bis(4-pyridylformamide)-1,4-benzene. The Nd—O bond lengths range from 2.513 (2) to 2.554 (2) Å, with an average value of 2.538 Å, compared to 2.671 (2) Å of Nd—N bond. Each Nd^III center displays a distorted bicapped square-antiprismic geometry. The first square is constructed by three oxygen atoms (O2, O4ⁱ and O5; symmetry code: (i) -x, y, -z + 1/2) and one nitrogen atom (N1), and the second square comprises of O2ⁱ, O4, O5ⁱ, and N3ⁱ atoms. The two oxygen atoms (O1 and O1ⁱ) occupy the two capping positions. The Nd atoms are located on a twofold axis. Thus, the adjacent mononuclear clusters are linked through the hydrogen-bonding interactions (N4—H4A···O1ⁱⁱ, N5—H5A···O7ⁱⁱ, N6—H6···N6ⁱⁱⁱ; symmetry codes: (ii) x, y + 1, z; (iii) -x + 1, -y + 4, -z), resulting in the formation of a two layered structure.

Related literature top

For general background to octacyanometallate-based compounds, see: Sieklucka et al. (2011); Zhou et al. (2010); Bok et al. (1975). For background to N,N'-bis(4-pyridylformamide)-1,4-benzene, see: Niu et al. (2004); Pansanel et al. (2006); Song et al. (2009).

Experimental top

Single crystals of the title compound were prepared at room temperature in the dark by slow diffusion of an acetonitrile solution (3 ml) containing Nd(NO₃)₃.6H₂O (0.05 mmol) and N,N'-bis(4-pyridylformamide)-1,4-benzene (0.05 mmol) into an acetonitrile solution (15 ml) of [HN(n-C₄H₉)₃]₃[Mo(CN)₈] (0.05 mmol) (Bok et al., 1975). After two weeks, yellow block crystals were obtained.

Structure description top

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SMART (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008.

Figures top

	Fig. 1. ORTEP diagram of the title compound. All hydrogen atoms bonded to carbon atoms have been omitted for clarity and thermal ellipsoids are presented at the 30% probability level. Symmetry code: (i) -x, y, -z + 1/2.
	Fig. 2. Perspective view of the title compound, showing the hydrogen-bonding interactions between adjacent mononuclear clusters.

Tetrakis(nitrato-κ²O,O')[N,N'-1,4- phenylenebis(pyridine-4-carboxamide)-κN¹](4-{[4-(pyridine-4- carboxamido-κN¹)phenyl]carbamoyl}pyridin-1-ium)neodymium(III) top

Crystal data top

[Nd(NO₃)₄(C₁₈H₁₅N₄O₂)(C₁₈H₁₄N₄O₂)]	F(000) = 2068
M_r = 1029.95	D_x = 1.739 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5566 reflections
a = 19.856 (4) Å	θ = 2.5–25.6°
b = 7.8491 (14) Å	µ = 1.41 mm⁻¹
c = 25.338 (5) Å	T = 291 K
β = 95.153 (2)°	Block, yellow
V = 3933.0 (13) Å³	0.28 × 0.24 × 0.22 mm
Z = 4

Data collection top

Bruker SMART APEX CCD diffractometer	3853 independent reflections
Radiation source: fine-focus sealed tube	3510 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
φ and ω scans	θ_max = 26.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −24→24
T_min = 0.693, T_max = 0.746	k = −8→9
14547 measured reflections	l = −31→31

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.070	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0368P)² + 4.9413P] where P = (F_o² + 2F_c²)/3
3853 reflections	(Δ/σ)_max < 0.001
294 parameters	Δρ_max = 1.29 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

[Nd(NO₃)₄(C₁₈H₁₅N₄O₂)(C₁₈H₁₄N₄O₂)]	V = 3933.0 (13) Å³
M_r = 1029.95	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 19.856 (4) Å	µ = 1.41 mm⁻¹
b = 7.8491 (14) Å	T = 291 K
c = 25.338 (5) Å	0.28 × 0.24 × 0.22 mm
β = 95.153 (2)°

Data collection top

Bruker SMART APEX CCD diffractometer	3853 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	3510 reflections with I > 2σ(I)
T_min = 0.693, T_max = 0.746	R_int = 0.040
14547 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.070	H-atom parameters constrained
S = 0.99	Δρ_max = 1.29 e Å⁻³
3853 reflections	Δρ_min = −0.36 e Å⁻³
294 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	Occ. (<1)
Nd1	0.0000	0.03144 (3)	0.2500	0.02816 (8)
O1	0.12544 (12)	−0.0024 (3)	0.23734 (10)	0.0500 (6)
N1	0.05042 (13)	0.2942 (3)	0.19938 (10)	0.0375 (6)
C1	0.08058 (16)	0.4270 (4)	0.22500 (13)	0.0410 (7)
H1	0.0736	0.4421	0.2605	0.049*
O2	0.10174 (13)	0.1272 (3)	0.30864 (9)	0.0541 (6)
N2	0.14665 (14)	0.0697 (4)	0.28005 (13)	0.0522 (8)
C2	0.12163 (16)	0.5434 (4)	0.20184 (12)	0.0391 (7)
H2	0.1411	0.6339	0.2214	0.047*
O3	0.20657 (14)	0.0853 (5)	0.29318 (15)	0.0981 (12)
N3	−0.02515 (13)	−0.2346 (3)	0.16730 (10)	0.0386 (6)
C3	0.13313 (14)	0.5224 (4)	0.14925 (12)	0.0345 (6)
O4	−0.05520 (12)	−0.2346 (3)	0.20850 (9)	0.0493 (6)
N4	0.18418 (12)	0.7980 (3)	0.13715 (10)	0.0390 (6)
H4A	0.1615	0.8285	0.1644	0.047*
C4	0.10281 (17)	0.3846 (4)	0.12217 (12)	0.0412 (7)
H4	0.1097	0.3652	0.0868	0.049*
O5	0.01619 (12)	−0.1125 (3)	0.16218 (9)	0.0497 (6)
N5	0.32465 (13)	1.3637 (3)	0.06645 (11)	0.0425 (6)
H5A	0.3067	1.4584	0.0785	0.051*
C5	0.06243 (16)	0.2773 (4)	0.14848 (12)	0.0413 (7)
H5	0.0420	0.1866	0.1296	0.050*
O6	−0.03444 (14)	−0.3447 (4)	0.13396 (10)	0.0657 (7)
N6	0.45861 (13)	1.8629 (3)	0.00603 (11)	0.0449 (7)
H6	0.4815	1.9600	0.0045	0.054*	0.50
C6	0.17860 (15)	0.6371 (4)	0.11988 (12)	0.0358 (7)
O7	0.20613 (13)	0.5820 (3)	0.08216 (10)	0.0566 (6)
C7	0.22349 (15)	0.9311 (4)	0.11767 (13)	0.0366 (7)
O8	0.38974 (12)	1.2586 (3)	0.00483 (10)	0.0542 (6)
C8	0.23701 (19)	1.0708 (4)	0.15034 (14)	0.0516 (9)
H8	0.2231	1.0708	0.1844	0.062*
C9	0.27096 (19)	1.2096 (5)	0.13266 (14)	0.0525 (9)
H9	0.2790	1.3035	0.1547	0.063*
C10	0.29314 (15)	1.2111 (4)	0.08252 (12)	0.0384 (7)
C11	0.28130 (16)	1.0710 (4)	0.05014 (13)	0.0404 (7)
H11	0.2966	1.0703	0.0165	0.048*
C12	0.24663 (16)	0.9308 (4)	0.06760 (13)	0.0401 (7)
H12	0.2389	0.8366	0.0456	0.048*
C13	0.36928 (15)	1.3780 (4)	0.02994 (12)	0.0376 (7)
C14	0.39656 (15)	1.5559 (4)	0.02252 (12)	0.0363 (7)
C15	0.39694 (17)	1.6835 (4)	0.05940 (13)	0.0445 (8)
H15	0.3761	1.6679	0.0905	0.053*
C16	0.42859 (18)	1.8357 (4)	0.04990 (14)	0.0490 (8)
H16	0.4288	1.9219	0.0751	0.059*
C17	0.45621 (16)	1.7421 (5)	−0.03105 (13)	0.0470 (8)
H17	0.4757	1.7630	−0.0624	0.056*
C18	0.42595 (16)	1.5886 (4)	−0.02424 (13)	0.0432 (7)
H18	0.4250	1.5063	−0.0507	0.052*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Nd1	0.03137 (12)	0.02393 (12)	0.03054 (12)	0.000	0.01028 (8)	0.000
O1	0.0389 (12)	0.0579 (16)	0.0550 (15)	0.0037 (10)	0.0140 (11)	0.0070 (11)
N1	0.0421 (14)	0.0277 (14)	0.0441 (15)	−0.0043 (11)	0.0117 (11)	0.0039 (11)
C1	0.0498 (18)	0.0317 (18)	0.0434 (17)	−0.0036 (14)	0.0149 (14)	0.0018 (13)
O2	0.0614 (16)	0.0571 (16)	0.0424 (13)	−0.0094 (12)	−0.0036 (11)	−0.0003 (11)
N2	0.0366 (15)	0.058 (2)	0.061 (2)	−0.0048 (13)	−0.0022 (14)	0.0215 (15)
C2	0.0446 (17)	0.0303 (16)	0.0434 (17)	−0.0051 (13)	0.0097 (13)	−0.0034 (13)
O3	0.0409 (16)	0.122 (3)	0.126 (3)	−0.0114 (17)	−0.0256 (17)	0.027 (2)
N3	0.0445 (15)	0.0312 (14)	0.0406 (14)	−0.0007 (11)	0.0067 (11)	−0.0052 (11)
C3	0.0329 (14)	0.0270 (15)	0.0445 (17)	0.0001 (12)	0.0085 (12)	0.0048 (12)
O4	0.0651 (15)	0.0403 (13)	0.0457 (13)	−0.0136 (11)	0.0228 (11)	−0.0057 (10)
N4	0.0403 (14)	0.0321 (15)	0.0472 (15)	−0.0051 (11)	0.0187 (11)	0.0033 (11)
C4	0.0526 (19)	0.0349 (18)	0.0373 (16)	−0.0075 (15)	0.0105 (14)	0.0009 (13)
O5	0.0597 (14)	0.0437 (14)	0.0494 (13)	−0.0146 (12)	0.0247 (11)	−0.0082 (11)
N5	0.0478 (15)	0.0272 (14)	0.0557 (16)	−0.0075 (11)	0.0226 (13)	−0.0010 (11)
C5	0.0478 (18)	0.0334 (17)	0.0430 (18)	−0.0086 (14)	0.0050 (14)	0.0015 (13)
O6	0.0768 (18)	0.0620 (18)	0.0598 (16)	−0.0183 (14)	0.0153 (13)	−0.0294 (13)
N6	0.0406 (15)	0.0378 (16)	0.0565 (17)	−0.0121 (12)	0.0053 (12)	0.0087 (13)
C6	0.0349 (15)	0.0312 (17)	0.0424 (17)	−0.0015 (12)	0.0102 (13)	0.0020 (12)
O7	0.0724 (17)	0.0382 (13)	0.0647 (16)	−0.0087 (12)	0.0373 (13)	−0.0040 (11)
C7	0.0339 (15)	0.0279 (17)	0.0495 (18)	−0.0045 (12)	0.0117 (13)	0.0043 (12)
O8	0.0538 (14)	0.0405 (14)	0.0723 (16)	−0.0109 (11)	0.0276 (12)	−0.0106 (12)
C8	0.067 (2)	0.043 (2)	0.049 (2)	−0.0161 (17)	0.0284 (17)	−0.0039 (15)
C9	0.066 (2)	0.042 (2)	0.053 (2)	−0.0170 (17)	0.0239 (17)	−0.0108 (16)
C10	0.0352 (15)	0.0317 (17)	0.0498 (18)	−0.0056 (13)	0.0123 (13)	0.0026 (13)
C11	0.0438 (17)	0.0389 (19)	0.0396 (17)	−0.0097 (14)	0.0100 (13)	0.0025 (13)
C12	0.0432 (17)	0.0326 (18)	0.0451 (18)	−0.0092 (13)	0.0081 (14)	−0.0016 (13)
C13	0.0333 (15)	0.0381 (19)	0.0422 (17)	−0.0051 (13)	0.0074 (13)	−0.0019 (14)
C14	0.0320 (15)	0.0371 (18)	0.0405 (16)	−0.0055 (12)	0.0074 (12)	0.0030 (13)
C15	0.0502 (19)	0.043 (2)	0.0416 (17)	−0.0131 (15)	0.0125 (14)	−0.0019 (14)
C16	0.053 (2)	0.0404 (19)	0.054 (2)	−0.0121 (16)	0.0068 (16)	−0.0053 (15)
C17	0.0449 (18)	0.050 (2)	0.0473 (19)	−0.0064 (16)	0.0122 (15)	0.0096 (16)
C18	0.0439 (18)	0.0451 (19)	0.0422 (17)	−0.0077 (15)	0.0122 (14)	−0.0024 (14)

Geometric parameters (Å, º) top

Nd1—O2	2.513 (2)	C4—H4	0.9300
Nd1—O2ⁱ	2.513 (2)	N5—C13	1.342 (4)
Nd1—O5	2.542 (2)	N5—C10	1.428 (4)
Nd1—O5ⁱ	2.542 (2)	N5—H5A	0.8900
Nd1—O4	2.542 (2)	C5—H5	0.9300
Nd1—O4ⁱ	2.542 (2)	N6—C16	1.325 (4)
Nd1—O1ⁱ	2.554 (2)	N6—C17	1.333 (4)
Nd1—O1	2.554 (2)	N6—H6	0.8900
Nd1—N1	2.671 (2)	C6—O7	1.222 (4)
Nd1—N1ⁱ	2.671 (2)	C7—C8	1.385 (5)
Nd1—N2ⁱ	2.958 (3)	C7—C12	1.388 (4)
Nd1—N2	2.958 (3)	O8—C13	1.222 (4)
O1—N2	1.260 (4)	C8—C9	1.377 (5)
N1—C1	1.340 (4)	C8—H8	0.9300
N1—C5	1.339 (4)	C9—C10	1.382 (4)
C1—C2	1.389 (4)	C9—H9	0.9300
C1—H1	0.9300	C10—C11	1.380 (4)
O2—N2	1.281 (4)	C11—C12	1.391 (4)
N2—O3	1.213 (4)	C11—H11	0.9300
C2—C3	1.382 (4)	C12—H12	0.9300
C2—H2	0.9300	C13—C14	1.516 (4)
N3—O6	1.211 (3)	C14—C15	1.369 (4)
N3—O4	1.248 (3)	C14—C18	1.391 (4)
N3—O5	1.276 (3)	C15—C16	1.381 (5)
C3—C4	1.389 (4)	C15—H15	0.9300
C3—C6	1.517 (4)	C16—H16	0.9300
N4—C6	1.338 (4)	C17—C18	1.364 (5)
N4—C7	1.419 (4)	C17—H17	0.9300
N4—H4A	0.8902	C18—H18	0.9300
C4—C5	1.376 (4)

O2—Nd1—O2ⁱ	145.18 (12)	O3—N2—O1	121.7 (4)
O2—Nd1—O5	119.51 (8)	O3—N2—O2	121.7 (4)
O2ⁱ—Nd1—O5	76.91 (8)	O1—N2—O2	116.6 (3)
O2—Nd1—O5ⁱ	76.91 (8)	O3—N2—Nd1	179.0 (3)
O2ⁱ—Nd1—O5ⁱ	119.51 (8)	O1—N2—Nd1	59.20 (15)
O5—Nd1—O5ⁱ	127.20 (11)	O2—N2—Nd1	57.46 (15)
O2—Nd1—O4	141.65 (8)	C3—C2—C1	118.9 (3)
O2ⁱ—Nd1—O4	72.99 (8)	C3—C2—H2	120.6
O5—Nd1—O4	49.93 (7)	C1—C2—H2	120.6
O5ⁱ—Nd1—O4	85.01 (8)	O6—N3—O4	121.9 (3)
O2—Nd1—O4ⁱ	72.99 (8)	O6—N3—O5	121.6 (3)
O2ⁱ—Nd1—O4ⁱ	141.65 (8)	O4—N3—O5	116.5 (2)
O5—Nd1—O4ⁱ	85.01 (8)	O6—N3—Nd1	178.8 (2)
O5ⁱ—Nd1—O4ⁱ	49.93 (7)	O4—N3—Nd1	58.16 (14)
O4—Nd1—O4ⁱ	69.51 (11)	O5—N3—Nd1	58.30 (14)
O2—Nd1—O1ⁱ	134.28 (8)	C2—C3—C4	117.9 (3)
O2ⁱ—Nd1—O1ⁱ	50.51 (8)	C2—C3—C6	124.0 (3)
O5—Nd1—O1ⁱ	105.38 (8)	C4—C3—C6	118.1 (3)
O5ⁱ—Nd1—O1ⁱ	69.04 (8)	N3—O4—Nd1	97.18 (16)
O4—Nd1—O1ⁱ	65.00 (8)	C6—N4—C7	127.8 (3)
O4ⁱ—Nd1—O1ⁱ	104.58 (8)	C6—N4—H4A	118.3
O2—Nd1—O1	50.51 (8)	C7—N4—H4A	113.8
O2ⁱ—Nd1—O1	134.28 (8)	C5—C4—C3	118.9 (3)
O5—Nd1—O1	69.04 (8)	C5—C4—H4	120.6
O5ⁱ—Nd1—O1	105.38 (8)	C3—C4—H4	120.6
O4—Nd1—O1	104.58 (8)	N3—O5—Nd1	96.42 (16)
O4ⁱ—Nd1—O1	65.00 (8)	C13—N5—C10	126.9 (3)
O1ⁱ—Nd1—O1	168.06 (11)	C13—N5—H5A	118.5
O2—Nd1—N1	74.74 (8)	C10—N5—H5A	113.8
O2ⁱ—Nd1—N1	78.52 (8)	N1—C5—C4	124.6 (3)
O5—Nd1—N1	80.83 (8)	N1—C5—H5	117.7
O5ⁱ—Nd1—N1	147.80 (8)	C4—C5—H5	117.7
O4—Nd1—N1	127.02 (7)	C16—N6—C17	119.1 (3)
O4ⁱ—Nd1—N1	131.83 (8)	C16—N6—H6	116.3
O1ⁱ—Nd1—N1	123.55 (8)	C17—N6—H6	124.4
O1—Nd1—N1	66.92 (8)	O7—C6—N4	124.1 (3)
O2—Nd1—N1ⁱ	78.52 (8)	O7—C6—C3	120.1 (3)
O2ⁱ—Nd1—N1ⁱ	74.74 (8)	N4—C6—C3	115.8 (3)
O5—Nd1—N1ⁱ	147.80 (8)	C8—C7—C12	119.0 (3)
O5ⁱ—Nd1—N1ⁱ	80.83 (8)	C8—C7—N4	117.3 (3)
O4—Nd1—N1ⁱ	131.83 (8)	C12—C7—N4	123.7 (3)
O4ⁱ—Nd1—N1ⁱ	127.02 (7)	C9—C8—C7	120.4 (3)
O1ⁱ—Nd1—N1ⁱ	66.92 (8)	C9—C8—H8	119.8
O1—Nd1—N1ⁱ	123.55 (8)	C7—C8—H8	119.8
N1—Nd1—N1ⁱ	78.88 (11)	C10—C9—C8	120.8 (3)
O2—Nd1—N2ⁱ	147.38 (8)	C10—C9—H9	119.6
O2ⁱ—Nd1—N2ⁱ	25.44 (8)	C8—C9—H9	119.6
O5—Nd1—N2ⁱ	91.07 (8)	C9—C10—C11	119.3 (3)
O5ⁱ—Nd1—N2ⁱ	94.10 (9)	C9—C10—N5	117.0 (3)
O4—Nd1—N2ⁱ	66.36 (8)	C11—C10—N5	123.7 (3)
O4ⁱ—Nd1—N2ⁱ	124.59 (9)	C10—C11—C12	120.3 (3)
O1ⁱ—Nd1—N2ⁱ	25.07 (9)	C10—C11—H11	119.9
O1—Nd1—N2ⁱ	157.96 (8)	C12—C11—H11	119.9
N1—Nd1—N2ⁱ	101.58 (9)	C7—C12—C11	120.2 (3)
N1ⁱ—Nd1—N2ⁱ	69.05 (8)	C7—C12—H12	119.9
O2—Nd1—N2	25.44 (8)	C11—C12—H12	119.9
O2ⁱ—Nd1—N2	147.38 (8)	O8—C13—N5	124.5 (3)
O5—Nd1—N2	94.10 (9)	O8—C13—C14	120.2 (3)
O5ⁱ—Nd1—N2	91.07 (8)	N5—C13—C14	115.3 (3)
O4—Nd1—N2	124.59 (9)	C15—C14—C18	118.0 (3)
O4ⁱ—Nd1—N2	66.36 (8)	C15—C14—C13	124.7 (3)
O1ⁱ—Nd1—N2	157.96 (8)	C18—C14—C13	117.2 (3)
O1—Nd1—N2	25.07 (9)	C14—C15—C16	119.2 (3)
N1—Nd1—N2	69.05 (8)	C14—C15—H15	120.4
N1ⁱ—Nd1—N2	101.58 (9)	C16—C15—H15	120.4
N2ⁱ—Nd1—N2	168.35 (12)	N6—C16—C15	122.1 (3)
N2—O1—Nd1	95.73 (19)	N6—C16—H16	118.9
C1—N1—C5	115.7 (3)	C15—C16—H16	118.9
C1—N1—Nd1	122.6 (2)	N6—C17—C18	121.8 (3)
C5—N1—Nd1	119.53 (19)	N6—C17—H17	119.1
N1—C1—C2	124.1 (3)	C18—C17—H17	119.1
N1—C1—H1	118.0	C17—C18—C14	119.6 (3)
C2—C1—H1	118.0	C17—C18—H18	120.2
N2—O2—Nd1	97.10 (18)	C14—C18—H18	120.2

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O1ⁱⁱ	0.89	2.43	3.285 (4)	160
N5—H5A···O7ⁱⁱ	0.89	2.23	2.966 (4)	140
N6—H6···N6ⁱⁱⁱ	0.89	1.86	2.742 (5)	168

Symmetry codes: (ii) x, y+1, z; (iii) −x+1, −y+4, −z.

Experimental details

Crystal data
Chemical formula	[Nd(NO₃)₄(C₁₈H₁₅N₄O₂)(C₁₈H₁₄N₄O₂)]
M_r	1029.95
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	291
a, b, c (Å)	19.856 (4), 7.8491 (14), 25.338 (5)
β (°)	95.153 (2)
V (Å³)	3933.0 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.41
Crystal size (mm)	0.28 × 0.24 × 0.22

Data collection
Diffractometer	Bruker SMART APEX CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.693, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	14547, 3853, 3510
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.070, 0.99
No. of reflections	3853
No. of parameters	294
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.29, −0.36

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXTL (Sheldrick, 2008), DIAMOND (Brandenburg, 2006), SHELXTL (Sheldrick, 2008.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O1ⁱ	0.89	2.43	3.285 (4)	159.9
N5—H5A···O7ⁱ	0.89	2.23	2.966 (4)	140.0
N6—H6···N6ⁱⁱ	0.89	1.86	2.742 (5)	168.4

Symmetry codes: (i) x, y+1, z; (ii) −x+1, −y+4, −z.

Acknowledgements

The work was supported by the Natural Science Foundation of Jiangsu Province (grant No. BK2011518) and the Project of Jiangsu University of Science and Technology (grant No. 2009 C L152J).

References

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