Trichloridotris{N-[phen­yl(pyridin-2-yl)methyl­idene]hydroxyl­amine-κ2N,N′}neodymium(III)

Yang, H.

doi:10.1107/S1600536812014055

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Pages m578-m579

doi:10.1107/S1600536812014055

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Trichloridotris{N-[phenyl(pyridin-2-yl)methylidene]hydroxylamine-κ²N,N′}neodymium(III)

Hua Yang ^a ^*

^aCollege of Chemistry and Chemical Engineering, Yan'an University, Yan'an, Shaanxi 716000, People's Republic of China
^*Correspondence e-mail: yanghua7687@163.com

(Received 16 March 2012; accepted 31 March 2012; online 13 April 2012)

In the title compound, [NdCl₃(C₁₂H₁₀N₂O)₃], the central Nd^III ion is nine-coordinated by six N atoms from three bidentate chelate N-[phenyl(pyridin-2-yl)methylidene]hydroxylamine ligands and three Cl⁻ ions, and displays a distorted tricapped trigonal prismatic geometry. The complex molecules are stabilized by intramolecular O—H⋯Cl hydrogen bonds.

Related literature

For complexes of oximes, see: Kukushkin & Pombeiro (1999 ); Milios et al. (2007 ); Fritsky et al. (2004 ); Xu et al. (2007 ); Papatriantafyllopoulou et al. (2009 ). For 3d-metal complexes of N-[phenyl(pyridine-2-yl)methylidene]hydroxylamine, see: Milios et al. (2003 ); Milios et al. (2004 ). For an Sm complex with this ligand, see: Lei et al. (2012 ).

Experimental

Crystal data

[NdCl₃(C₁₂H₁₀N₂O)₃]
M_r = 845.25
Triclinic, $[P \overline 1]$
a = 8.6367 (17) Å
b = 10.460 (2) Å
c = 19.847 (4) Å
α = 91.87 (3)°
β = 94.38 (3)°
γ = 92.80 (3)°
V = 1784.4 (6) Å³
Z = 2
Mo Kα radiation
μ = 1.72 mm⁻¹
T = 293 K
0.31 × 0.18 × 0.13 mm

Data collection

Bruker SMART CCD-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.617, T_max = 0.807
30524 measured reflections
7775 independent reflections
7155 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.022
wR(F²) = 0.059
S = 1.04
7775 reflections
445 parameters
H-atom parameters constrained
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.44 e Å⁻³

Table 1
Selected bond lengths (Å)

Nd1—N2	2.604 (2)
Nd1—N1	2.661 (2)
Nd1—N5	2.680 (2)
Nd1—N4	2.6953 (19)
Nd1—N6	2.7018 (19)
Nd1—N3	2.742 (2)
Nd1—Cl3	2.7686 (8)
Nd1—Cl2	2.7903 (9)
Nd1—Cl1	2.8296 (10)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯Cl3	0.82	2.22	2.966 (2)	152
O2—H2A⋯Cl1	0.82	2.19	2.9290 (19)	151
O3—H3A⋯Cl2	0.82	2.19	2.930 (2)	150

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); 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 I, global. DOI: 10.1107/S1600536812014055/zs2190sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812014055/zs2190Isup2.hkl

checkCIF report

Comment top

The coordination chemistry of oximes (Kukushkin & Pombeiro, 1999; Milios et al., 2007) continues to attract considerable attention, with the efforts of several research groups driven by a number of considerations. These include the use of metal oxime complexes in supramolecular chemistry (Fritsky et al., 2004) and the employment of oximate ligands in the synthesis of complexes with interesting magnetic properties (Xu et al., 2007; Papatriantafyllopoulou et al., 2009; Milios et al., 2007). N-[phenyl(pyridine-2-yl)methylidene]hydroxylamine [(py)C(ph)NOH], is one of the oximes that is currently a popular ligand for synthesis of the 3d-metal complexes (Milios et al., 2003; Milios et al., 2004). However, the structures of rare earth metal complexes with this ligand are uncommon in the crystallographic literature. Here we report the structure of the neodymium complex with [(py)C(ph)NOH], the title compound [NdCl₃(C₁₂H₁₀N₂O)₃], which was synthesized by the reaction of NdCl₃ . 6H₂O with the ligand under autogenous pressure. The title compound is isomorphous with the Sm^III analogue (Lei et al., 2012).

In the title complex, the central Nd^III ion is nine-coordinated by six nitrogen atoms from three bidentate chelate ligands and three Cl^- ions [Nd—N range, 2.604 (2)–2.742 (2) Å; Nd—Cl, 2.7686 (8)–2.8296 (10) Å (Table 1)] and displays a distorted tricapped trigonal prismatic geometry (Fig. 1). The discrete complex molecules are stabilized by intramolecular O—H···Cl hydrogen bonds (Table 2, Fig. 2).

Related literature top

For complexes of oximes, see: Kukushkin & Pombeiro (1999); Milios et al. (2007); Fritsky et al. (2004); Xu et al. (2007); Papatriantafyllopoulou et al. (2009). For 3d-metal complexes of N-[phenyl(pyridine-2-yl)methylidene]hydroxylamine, see: Milios et al. (2003); Milios et al. (2004). For an Sm complex with this ligand, see: Lei et al. (2012).

Experimental top

A mixture of phenyl-2-pyridyl ketone oxime (0.0198 g, 0.10 mmol), NdCl₃ . 6H₂O (0.0179 g, 0.05 mmol), and ethanol (2 mL) was sealed in a 6 mL Pyrex tube. The tube was heated at 80 °C for 4 days under autogenous pressure. Cooling of the resultant solution to room temperature gave colourless crystals of the product. The crystals were collected by filtration, washed with ethanol (2 mL) and dried in air. Yield: 54%. Anal. Calcd. for C₃₆H₃₀Cl₃N₆NdO₃: C, 51.15; H, 3.58; N, 9.94%. Found: C, 50.93; H, 3.43; N, 9.76%.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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 molecular structure of the title complex, showing atom labels and 30% probability displacement ellipsoids.
	Fig. 2. Intramolecular hydrogen-bonding interactions in the title complex, with hydrogen bonds shown as dashed lines.

Trichloridotris{N-[phenyl(pyridin-2-yl)methylidene]hydroxylamine- κ²N,N'}neodymium(III) top

Crystal data top

[NdCl₃(C₁₂H₁₀N₂O)₃]	Z = 2
M_r = 845.25	F(000) = 846
Triclinic, P1	char
Hall symbol: -P 1	D_x = 1.573 Mg m⁻³
a = 8.6367 (17) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.460 (2) Å	Cell parameters from 7737 reflections
c = 19.847 (4) Å	θ = 2.2–27.0°
α = 91.87 (3)°	µ = 1.72 mm⁻¹
β = 94.38 (3)°	T = 293 K
γ = 92.80 (3)°	Block, colourless
V = 1784.4 (6) Å³	0.31 × 0.18 × 0.13 mm

Data collection top

Bruker SMART CCD-detector diffractometer	7775 independent reflections
Radiation source: fine-focus sealed tube	7155 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ϕ and ω scans	θ_max = 27.0°, θ_min = 1.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −11→11
T_min = 0.617, T_max = 0.807	k = −13→13
30524 measured reflections	l = −25→25

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)] = 0.022	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.059	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0316P)² + 0.3895P] where P = (F_o² + 2F_c²)/3
7775 reflections	(Δ/σ)_max = 0.002
445 parameters	Δρ_max = 0.50 e Å⁻³
0 restraints	Δρ_min = −0.44 e Å⁻³

Crystal data top

[NdCl₃(C₁₂H₁₀N₂O)₃]	γ = 92.80 (3)°
M_r = 845.25	V = 1784.4 (6) Å³
Triclinic, P1	Z = 2
a = 8.6367 (17) Å	Mo Kα radiation
b = 10.460 (2) Å	µ = 1.72 mm⁻¹
c = 19.847 (4) Å	T = 293 K
α = 91.87 (3)°	0.31 × 0.18 × 0.13 mm
β = 94.38 (3)°

Data collection top

Bruker SMART CCD-detector diffractometer	7775 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	7155 reflections with I > 2σ(I)
T_min = 0.617, T_max = 0.807	R_int = 0.028
30524 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.022	0 restraints
wR(F²) = 0.059	H-atom parameters constrained
S = 1.04	Δρ_max = 0.50 e Å⁻³
7775 reflections	Δρ_min = −0.44 e Å⁻³
445 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
Nd1	0.170030 (12)	0.594157 (10)	0.248609 (5)	0.03370 (4)
Cl2	0.10720 (8)	0.35456 (5)	0.30113 (3)	0.05379 (15)
Cl1	0.27975 (7)	0.70288 (6)	0.13140 (3)	0.05048 (14)
Cl3	0.48680 (7)	0.57109 (6)	0.27455 (3)	0.05349 (15)
N2	0.2436 (2)	0.41331 (18)	0.16542 (10)	0.0429 (4)
N6	0.2375 (2)	0.61037 (18)	0.38390 (9)	0.0437 (4)
N1	−0.0455 (2)	0.48814 (17)	0.15808 (9)	0.0397 (4)
N3	−0.0819 (2)	0.65372 (18)	0.31740 (9)	0.0415 (4)
N5	0.2564 (2)	0.81945 (17)	0.31196 (10)	0.0434 (4)
C27	0.3334 (5)	1.0579 (3)	0.37346 (19)	0.0884 (11)
H27	0.3572	1.1381	0.3943	0.106*
N4	−0.0185 (2)	0.77901 (18)	0.20749 (9)	0.0418 (4)
C7	0.2007 (3)	0.2515 (2)	0.07372 (11)	0.0416 (5)
C18	−0.1209 (2)	0.8276 (2)	0.24228 (11)	0.0378 (4)
O1	0.3882 (2)	0.36271 (19)	0.17316 (10)	0.0627 (5)
H1A	0.4419	0.4034	0.2031	0.094*
O2	−0.0065 (2)	0.83670 (19)	0.14624 (9)	0.0592 (5)
H2A	0.0687	0.8104	0.1282	0.089*
C19	−0.2129 (3)	0.9365 (2)	0.21929 (11)	0.0397 (5)
C5	−0.0047 (3)	0.4056 (2)	0.10935 (11)	0.0394 (5)
O3	0.2290 (2)	0.50316 (16)	0.42307 (8)	0.0576 (4)
H3A	0.2028	0.4398	0.3987	0.086*
C17	−0.1480 (2)	0.7670 (2)	0.30694 (11)	0.0384 (5)
C13	−0.1152 (3)	0.5941 (2)	0.37345 (13)	0.0502 (6)
H13	−0.0759	0.5139	0.3803	0.060*
C31	0.2881 (3)	0.7204 (3)	0.49380 (12)	0.0508 (6)
C6	0.1547 (3)	0.3581 (2)	0.11766 (11)	0.0399 (5)
C21	−0.2296 (4)	1.1591 (3)	0.19732 (14)	0.0624 (7)
H21	−0.1853	1.2421	0.1996	0.075*
C1	−0.1928 (3)	0.5235 (2)	0.15376 (12)	0.0459 (5)
H1	−0.2241	0.5772	0.1879	0.055*
C4	−0.1058 (3)	0.3652 (3)	0.05469 (12)	0.0521 (6)
H4	−0.0734	0.3112	0.0210	0.063*
C30	0.2678 (3)	0.7144 (2)	0.41872 (11)	0.0440 (5)
C24	−0.3642 (3)	0.9139 (3)	0.19283 (13)	0.0512 (6)
H24	−0.4110	0.8319	0.1923	0.061*
C14	−0.2040 (3)	0.6440 (3)	0.42155 (13)	0.0569 (6)
H14	−0.2222	0.5994	0.4602	0.068*
C25	0.2728 (3)	0.9250 (2)	0.27624 (14)	0.0537 (6)
H25	0.2582	0.9167	0.2294	0.064*
C20	−0.1452 (3)	1.0601 (2)	0.22234 (13)	0.0516 (6)
H20	−0.0437	1.0759	0.2411	0.062*
C29	0.2820 (3)	0.8323 (2)	0.37946 (12)	0.0475 (5)
C23	−0.4461 (3)	1.0143 (3)	0.16705 (14)	0.0630 (7)
H23	−0.5476	0.9994	0.1482	0.076*
C32	0.4105 (3)	0.6620 (3)	0.52790 (13)	0.0559 (6)
H32	0.4837	0.6224	0.5036	0.067*
C16	−0.2384 (3)	0.8229 (2)	0.35265 (13)	0.0516 (6)
H16	−0.2810	0.9013	0.3441	0.062*
C33	0.4240 (4)	0.6624 (3)	0.59736 (15)	0.0744 (9)
H33	0.5055	0.6222	0.6199	0.089*
C11	0.1861 (4)	0.0299 (3)	0.03858 (14)	0.0635 (7)
H11	0.1448	−0.0530	0.0427	0.076*
C12	0.1387 (3)	0.1293 (2)	0.07905 (13)	0.0549 (6)
H12	0.0648	0.1129	0.1098	0.066*
C2	−0.3004 (3)	0.4845 (3)	0.10144 (14)	0.0554 (6)
H2	−0.4018	0.5110	0.1006	0.067*
C22	−0.3780 (4)	1.1357 (3)	0.16916 (14)	0.0676 (8)
H22	−0.4332	1.2026	0.1513	0.081*
C8	0.3121 (3)	0.2733 (3)	0.02820 (14)	0.0605 (7)
H8	0.3573	0.3552	0.0250	0.073*
C9	0.3564 (4)	0.1743 (3)	−0.01235 (15)	0.0738 (9)
H9	0.4298	0.1897	−0.0434	0.089*
C3	−0.2561 (3)	0.4062 (3)	0.05076 (14)	0.0612 (7)
H3	−0.3258	0.3808	0.0142	0.073*
C15	−0.2652 (3)	0.7611 (3)	0.41137 (14)	0.0597 (7)
H15	−0.3238	0.7982	0.4435	0.072*
C35	0.1970 (5)	0.7814 (4)	0.60097 (17)	0.0867 (11)
H35	0.1257	0.8220	0.6260	0.104*
C26	0.3100 (4)	1.0446 (3)	0.30484 (18)	0.0729 (8)
H26	0.3191	1.1153	0.2780	0.087*
C10	0.2927 (4)	0.0537 (3)	−0.00695 (14)	0.0663 (8)
H10	0.3223	−0.0128	−0.0346	0.080*
C36	0.1811 (4)	0.7812 (3)	0.53085 (15)	0.0708 (8)
H36	0.0992	0.8216	0.5088	0.085*
C34	0.3174 (5)	0.7219 (4)	0.63336 (16)	0.0888 (12)
H34	0.3270	0.7220	0.6803	0.107*
C28	0.3211 (4)	0.9497 (3)	0.41152 (16)	0.0735 (9)
H28	0.3391	0.9562	0.4583	0.088*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Nd1	0.03692 (7)	0.02906 (7)	0.03506 (7)	0.00424 (4)	0.00134 (4)	−0.00019 (4)
Cl2	0.0757 (4)	0.0322 (3)	0.0531 (3)	−0.0011 (3)	0.0043 (3)	0.0023 (2)
Cl1	0.0546 (3)	0.0522 (3)	0.0471 (3)	0.0083 (3)	0.0152 (3)	0.0057 (3)
Cl3	0.0391 (3)	0.0638 (4)	0.0559 (3)	0.0057 (3)	−0.0057 (2)	−0.0067 (3)
N2	0.0381 (9)	0.0402 (10)	0.0505 (11)	0.0122 (8)	0.0013 (8)	−0.0055 (8)
N6	0.0537 (11)	0.0375 (10)	0.0399 (10)	0.0020 (8)	0.0022 (8)	0.0021 (8)
N1	0.0399 (9)	0.0357 (10)	0.0434 (10)	0.0052 (8)	0.0020 (8)	−0.0007 (8)
N3	0.0434 (10)	0.0372 (10)	0.0449 (10)	0.0043 (8)	0.0065 (8)	0.0070 (8)
N5	0.0473 (10)	0.0341 (10)	0.0486 (11)	−0.0012 (8)	0.0056 (8)	−0.0010 (8)
C27	0.132 (3)	0.0428 (16)	0.087 (2)	−0.0277 (18)	0.021 (2)	−0.0182 (16)
N4	0.0471 (10)	0.0395 (10)	0.0406 (10)	0.0087 (8)	0.0080 (8)	0.0085 (8)
C7	0.0463 (12)	0.0391 (12)	0.0395 (11)	0.0083 (10)	0.0026 (9)	−0.0033 (9)
C18	0.0390 (11)	0.0327 (11)	0.0421 (11)	0.0045 (9)	0.0043 (9)	0.0014 (9)
O1	0.0439 (9)	0.0694 (12)	0.0732 (13)	0.0254 (9)	−0.0082 (8)	−0.0251 (10)
O2	0.0709 (12)	0.0669 (12)	0.0464 (9)	0.0307 (10)	0.0216 (8)	0.0219 (9)
C19	0.0465 (12)	0.0367 (11)	0.0378 (11)	0.0112 (9)	0.0092 (9)	0.0038 (9)
C5	0.0432 (11)	0.0347 (11)	0.0400 (11)	0.0033 (9)	0.0012 (9)	0.0004 (9)
O3	0.0852 (13)	0.0419 (9)	0.0445 (9)	0.0005 (9)	−0.0032 (9)	0.0069 (7)
C17	0.0398 (11)	0.0352 (11)	0.0402 (11)	0.0009 (9)	0.0047 (9)	0.0012 (9)
C13	0.0487 (13)	0.0478 (14)	0.0557 (14)	0.0033 (11)	0.0073 (11)	0.0153 (11)
C31	0.0542 (14)	0.0535 (15)	0.0435 (13)	−0.0110 (12)	0.0077 (11)	−0.0074 (11)
C6	0.0438 (12)	0.0349 (11)	0.0412 (11)	0.0060 (9)	0.0044 (9)	−0.0029 (9)
C21	0.087 (2)	0.0373 (13)	0.0674 (17)	0.0171 (13)	0.0259 (16)	0.0089 (12)
C1	0.0426 (12)	0.0432 (13)	0.0523 (13)	0.0081 (10)	0.0033 (10)	−0.0012 (10)
C4	0.0551 (14)	0.0561 (15)	0.0441 (13)	0.0093 (12)	−0.0024 (11)	−0.0088 (11)
C30	0.0434 (12)	0.0454 (13)	0.0424 (12)	−0.0003 (10)	0.0028 (9)	−0.0039 (10)
C24	0.0435 (13)	0.0515 (14)	0.0597 (15)	0.0071 (11)	0.0062 (11)	0.0058 (12)
C14	0.0586 (15)	0.0644 (17)	0.0491 (14)	−0.0020 (13)	0.0124 (12)	0.0132 (12)
C25	0.0626 (15)	0.0399 (13)	0.0585 (15)	−0.0035 (11)	0.0066 (12)	0.0045 (11)
C20	0.0555 (14)	0.0422 (13)	0.0585 (15)	0.0070 (11)	0.0094 (12)	0.0036 (11)
C29	0.0498 (13)	0.0422 (13)	0.0497 (13)	−0.0042 (10)	0.0073 (11)	−0.0068 (10)
C23	0.0500 (14)	0.084 (2)	0.0590 (16)	0.0265 (14)	0.0082 (12)	0.0115 (15)
C32	0.0616 (16)	0.0540 (15)	0.0503 (14)	−0.0100 (12)	0.0015 (12)	−0.0005 (12)
C16	0.0565 (14)	0.0481 (14)	0.0521 (14)	0.0096 (11)	0.0131 (11)	0.0009 (11)
C33	0.086 (2)	0.077 (2)	0.0556 (17)	−0.0239 (18)	−0.0106 (16)	0.0101 (15)
C11	0.089 (2)	0.0368 (13)	0.0653 (17)	0.0058 (13)	0.0113 (15)	−0.0059 (12)
C12	0.0658 (16)	0.0435 (14)	0.0570 (15)	0.0007 (12)	0.0186 (12)	−0.0038 (11)
C2	0.0427 (13)	0.0603 (16)	0.0625 (16)	0.0095 (12)	−0.0041 (11)	0.0003 (13)
C22	0.085 (2)	0.0652 (19)	0.0611 (17)	0.0458 (17)	0.0277 (15)	0.0205 (14)
C8	0.0739 (18)	0.0513 (15)	0.0576 (16)	−0.0027 (13)	0.0204 (14)	−0.0051 (12)
C9	0.084 (2)	0.078 (2)	0.0618 (17)	0.0028 (17)	0.0327 (16)	−0.0137 (15)
C3	0.0541 (15)	0.0714 (18)	0.0550 (15)	0.0049 (13)	−0.0141 (12)	−0.0037 (13)
C15	0.0648 (16)	0.0647 (17)	0.0521 (15)	0.0055 (14)	0.0203 (13)	0.0008 (13)
C35	0.100 (3)	0.098 (3)	0.063 (2)	−0.018 (2)	0.0377 (19)	−0.0240 (18)
C26	0.094 (2)	0.0370 (14)	0.088 (2)	−0.0098 (14)	0.0204 (18)	0.0034 (14)
C10	0.080 (2)	0.0618 (18)	0.0586 (16)	0.0186 (15)	0.0136 (15)	−0.0186 (14)
C36	0.0677 (18)	0.082 (2)	0.0618 (17)	−0.0014 (16)	0.0121 (14)	−0.0123 (15)
C34	0.115 (3)	0.103 (3)	0.0442 (16)	−0.040 (2)	0.0093 (19)	−0.0032 (17)
C28	0.102 (2)	0.0538 (17)	0.0621 (17)	−0.0224 (16)	0.0136 (16)	−0.0154 (14)

Geometric parameters (Å, º) top

Nd1—N2	2.604 (2)	C21—H21	0.9300
Nd1—N1	2.661 (2)	C1—C2	1.377 (3)
Nd1—N5	2.680 (2)	C1—H1	0.9300
Nd1—N4	2.6953 (19)	C4—C3	1.384 (4)
Nd1—N6	2.7018 (19)	C4—H4	0.9300
Nd1—N3	2.742 (2)	C30—C29	1.485 (3)
Nd1—Cl3	2.7686 (8)	C24—C23	1.384 (4)
Nd1—Cl2	2.7903 (9)	C24—H24	0.9300
Nd1—Cl1	2.8296 (10)	C14—C15	1.372 (4)
N2—C6	1.277 (3)	C14—H14	0.9300
N2—O1	1.380 (2)	C25—C26	1.370 (4)
N6—C30	1.275 (3)	C25—H25	0.9300
N6—O3	1.387 (2)	C20—H20	0.9300
N1—C1	1.339 (3)	C29—C28	1.380 (4)
N1—C5	1.354 (3)	C23—C22	1.371 (4)
N3—C13	1.336 (3)	C23—H23	0.9300
N3—C17	1.355 (3)	C32—C33	1.374 (4)
N5—C25	1.339 (3)	C32—H32	0.9300
N5—C29	1.342 (3)	C16—C15	1.380 (4)
C27—C26	1.363 (5)	C16—H16	0.9300
C27—C28	1.385 (4)	C33—C34	1.369 (5)
C27—H27	0.9300	C33—H33	0.9300
N4—C18	1.278 (3)	C11—C10	1.358 (4)
N4—O2	1.383 (2)	C11—C12	1.390 (4)
C7—C12	1.372 (3)	C11—H11	0.9300
C7—C8	1.386 (3)	C12—H12	0.9300
C7—C6	1.481 (3)	C2—C3	1.365 (4)
C18—C17	1.479 (3)	C2—H2	0.9300
C18—C19	1.485 (3)	C22—H22	0.9300
O1—H1A	0.8200	C8—C9	1.378 (4)
O2—H2A	0.8200	C8—H8	0.9300
C19—C24	1.377 (3)	C9—C10	1.362 (4)
C19—C20	1.390 (3)	C9—H9	0.9300
C5—C4	1.381 (3)	C3—H3	0.9300
C5—C6	1.485 (3)	C15—H15	0.9300
O3—H3A	0.8200	C35—C34	1.367 (5)
C17—C16	1.376 (3)	C35—C36	1.388 (4)
C13—C14	1.375 (4)	C35—H35	0.9300
C13—H13	0.9300	C26—H26	0.9300
C31—C32	1.389 (4)	C10—H10	0.9300
C31—C36	1.389 (4)	C36—H36	0.9300
C31—C30	1.486 (3)	C34—H34	0.9300
C21—C22	1.366 (4)	C28—H28	0.9300
C21—C20	1.379 (4)

N2—Nd1—N1	60.38 (6)	C7—C6—C5	120.62 (19)
N2—Nd1—N5	146.60 (6)	C22—C21—C20	120.3 (3)
N1—Nd1—N5	140.98 (6)	C22—C21—H21	119.9
N2—Nd1—N4	121.50 (6)	C20—C21—H21	119.9
N1—Nd1—N4	72.25 (6)	N1—C1—C2	123.5 (2)
N5—Nd1—N4	68.74 (6)	N1—C1—H1	118.3
N2—Nd1—N6	126.82 (6)	C2—C1—H1	118.3
N1—Nd1—N6	139.68 (6)	C5—C4—C3	119.1 (2)
N5—Nd1—N6	59.14 (6)	C5—C4—H4	120.4
N4—Nd1—N6	111.33 (6)	C3—C4—H4	120.4
N2—Nd1—N3	137.44 (6)	N6—C30—C29	115.7 (2)
N1—Nd1—N3	83.49 (6)	N6—C30—C31	123.3 (2)
N5—Nd1—N3	75.89 (6)	C29—C30—C31	121.0 (2)
N4—Nd1—N3	58.57 (6)	C19—C24—C23	119.5 (3)
N6—Nd1—N3	67.56 (6)	C19—C24—H24	120.3
N2—Nd1—Cl3	74.36 (5)	C23—C24—H24	120.3
N1—Nd1—Cl3	134.58 (4)	C15—C14—C13	118.6 (2)
N5—Nd1—Cl3	78.41 (5)	C15—C14—H14	120.7
N4—Nd1—Cl3	136.62 (5)	C13—C14—H14	120.7
N6—Nd1—Cl3	71.65 (5)	N5—C25—C26	123.7 (3)
N3—Nd1—Cl3	138.76 (4)	N5—C25—H25	118.1
N2—Nd1—Cl2	69.77 (5)	C26—C25—H25	118.1
N1—Nd1—Cl2	77.37 (5)	C21—C20—C19	119.4 (3)
N5—Nd1—Cl2	130.24 (4)	C21—C20—H20	120.3
N4—Nd1—Cl2	131.64 (4)	C19—C20—H20	120.3
N6—Nd1—Cl2	71.34 (5)	N5—C29—C28	121.7 (2)
N3—Nd1—Cl2	81.64 (5)	N5—C29—C30	117.4 (2)
Cl3—Nd1—Cl2	91.19 (4)	C28—C29—C30	120.9 (2)
N2—Nd1—Cl1	70.22 (5)	C22—C23—C24	120.2 (3)
N1—Nd1—Cl1	81.67 (5)	C22—C23—H23	119.9
N5—Nd1—Cl1	86.33 (5)	C24—C23—H23	119.9
N4—Nd1—Cl1	70.85 (5)	C33—C32—C31	120.5 (3)
N6—Nd1—Cl1	138.42 (5)	C33—C32—H32	119.8
N3—Nd1—Cl1	129.42 (4)	C31—C32—H32	119.8
Cl3—Nd1—Cl1	79.77 (3)	C17—C16—C15	119.1 (2)
Cl2—Nd1—Cl1	139.95 (3)	C17—C16—H16	120.5
C6—N2—O1	113.33 (18)	C15—C16—H16	120.5
C6—N2—Nd1	126.43 (14)	C34—C33—C32	119.9 (3)
O1—N2—Nd1	120.13 (13)	C34—C33—H33	120.0
C30—N6—O3	113.23 (18)	C32—C33—H33	120.0
C30—N6—Nd1	125.00 (15)	C10—C11—C12	120.1 (3)
O3—N6—Nd1	121.56 (13)	C10—C11—H11	120.0
C1—N1—C5	117.13 (19)	C12—C11—H11	120.0
C1—N1—Nd1	122.39 (15)	C7—C12—C11	120.2 (2)
C5—N1—Nd1	120.07 (14)	C7—C12—H12	119.9
C13—N3—C17	116.6 (2)	C11—C12—H12	119.9
C13—N3—Nd1	121.58 (15)	C3—C2—C1	119.0 (2)
C17—N3—Nd1	119.27 (14)	C3—C2—H2	120.5
C25—N5—C29	117.5 (2)	C1—C2—H2	120.5
C25—N5—Nd1	120.04 (16)	C21—C22—C23	120.4 (2)
C29—N5—Nd1	122.42 (15)	C21—C22—H22	119.8
C26—C27—C28	118.7 (3)	C23—C22—H22	119.8
C26—C27—H27	120.6	C9—C8—C7	120.3 (3)
C28—C27—H27	120.6	C9—C8—H8	119.8
C18—N4—O2	112.71 (17)	C7—C8—H8	119.8
C18—N4—Nd1	125.20 (14)	C10—C9—C8	120.1 (3)
O2—N4—Nd1	122.00 (12)	C10—C9—H9	120.0
C12—C7—C8	118.9 (2)	C8—C9—H9	120.0
C12—C7—C6	120.9 (2)	C2—C3—C4	119.0 (2)
C8—C7—C6	120.1 (2)	C2—C3—H3	120.5
N4—C18—C17	116.40 (18)	C4—C3—H3	120.5
N4—C18—C19	122.86 (19)	C14—C15—C16	118.9 (2)
C17—C18—C19	120.71 (18)	C14—C15—H15	120.6
N2—O1—H1A	109.5	C16—C15—H15	120.6
N4—O2—H2A	109.5	C34—C35—C36	120.1 (3)
C24—C19—C20	120.1 (2)	C34—C35—H35	120.0
C24—C19—C18	119.6 (2)	C36—C35—H35	120.0
C20—C19—C18	120.2 (2)	C27—C26—C25	118.7 (3)
N1—C5—C4	122.2 (2)	C27—C26—H26	120.6
N1—C5—C6	116.83 (19)	C25—C26—H26	120.6
C4—C5—C6	120.9 (2)	C11—C10—C9	120.5 (3)
N6—O3—H3A	109.5	C11—C10—H10	119.8
N3—C17—C16	122.7 (2)	C9—C10—H10	119.8
N3—C17—C18	116.38 (19)	C35—C36—C31	119.7 (3)
C16—C17—C18	120.9 (2)	C35—C36—H36	120.2
N3—C13—C14	124.0 (2)	C31—C36—H36	120.2
N3—C13—H13	118.0	C35—C34—C33	120.7 (3)
C14—C13—H13	118.0	C35—C34—H34	119.7
C32—C31—C36	119.1 (2)	C33—C34—H34	119.7
C32—C31—C30	120.8 (2)	C29—C28—C27	119.5 (3)
C36—C31—C30	120.1 (3)	C29—C28—H28	120.2
N2—C6—C7	124.1 (2)	C27—C28—H28	120.2
N2—C6—C5	115.26 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···Cl3	0.82	2.22	2.966 (2)	152
O2—H2A···Cl1	0.82	2.19	2.9290 (19)	151
O3—H3A···Cl2	0.82	2.19	2.930 (2)	150

Experimental details

Crystal data
Chemical formula	[NdCl₃(C₁₂H₁₀N₂O)₃]
M_r	845.25
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.6367 (17), 10.460 (2), 19.847 (4)
α, β, γ (°)	91.87 (3), 94.38 (3), 92.80 (3)
V (Å³)	1784.4 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.72
Crystal size (mm)	0.31 × 0.18 × 0.13

Data collection
Diffractometer	Bruker SMART CCD-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.617, 0.807
No. of measured, independent and observed [I > 2σ(I)] reflections	30524, 7775, 7155
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.022, 0.059, 1.04
No. of reflections	7775
No. of parameters	445
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.44

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Nd1—N2	2.604 (2)	Nd1—N3	2.742 (2)
Nd1—N1	2.661 (2)	Nd1—Cl3	2.7686 (8)
Nd1—N5	2.680 (2)	Nd1—Cl2	2.7903 (9)
Nd1—N4	2.6953 (19)	Nd1—Cl1	2.8296 (10)
Nd1—N6	2.7018 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···Cl3	0.82	2.22	2.966 (2)	152
O2—H2A···Cl1	0.82	2.19	2.9290 (19)	151
O3—H3A···Cl2	0.82	2.19	2.930 (2)	150

Acknowledgements

The author appreciates financial support from Yanan University (grant No. YD2011–20) and the Science and Technology Bureau of Yanan City (grant No. kn2009–16).

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