(1,10-Phenanthroline-κ2N,N′)tris­(3-phenyl­propanoato-κO)neodymium(III)

Zhong, H.; Yang, X.-M.; Luo, Q.-Y.; Xu, Y.-P.

doi:10.1107/S1600536807035350

Retracted: (1,10-Phenanthroline-κ²N,N′)tris(3-phenylpropanoato-κO)neodymium(III)

H. Zhong, X.-M. Yang, Q.-Y. Luo and Y.-P. Xu

The Nd^III atom in the title complex, [Nd(C₉H₉O₂)₃(C₁₂H₈N₂)], is coordinated by two N atoms of the 1,10-phenanthroline (phen) ligand and four O atoms of the three 3-phenylpropanoate ligands. This mononuclear complex is further extended into a supramolecular network structure via nonclassical hydrogen bonds between CH groups of 1,10-phenanthroline or 3-phenylpropanoate and O atoms of neighbouring 3-phenylpropanoate molecules.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807035350/at2346sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807035350/at2346Isup2.hkl Contains datablock I

CCDC reference: 1270872

checkCIF report

Key indicators

Single-crystal X-ray study
T = 273 K
Mean (C-C) = 0.015 Å
R factor = 0.043
wR factor = 0.188
Data-to-parameter ratio = 18.2

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for         C6
PLAT410_ALERT_2_B Short Intra H...H Contact  H14B   ..  H24B    ..       1.88 Ang.

Alert level C
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.82 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C27
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C33
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C16
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C25
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C32
PLAT332_ALERT_2_C Large Phenyl C-C Range           C34    -C39           0.17 Ang.
PLAT333_ALERT_2_C Large Average Benzene C-C Dist.  C4     -C6            1.45 Ang.
PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...         15
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C14    -   C15    ...       1.41 Ang.
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C32    -   C33    ...       1.37 Ang.
PLAT362_ALERT_2_C Short  C(sp3)-C(sp2) Bond  C15    -   C16    ...       1.39 Ang.
PLAT362_ALERT_2_C Short  C(sp3)-C(sp2) Bond  C24    -   C25    ...       1.37 Ang.
PLAT362_ALERT_2_C Short  C(sp3)-C(sp2) Bond  C33    -   C34    ...       1.34 Ang.
PLAT410_ALERT_2_C Short Intra H...H Contact  H12    ..  H24A    ..       1.90 Ang.
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .      77.00 A   3 

Alert level G
PLAT794_ALERT_5_G Check Predicted Bond Valency for Nd1         (3)       2.58
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          4

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
  17 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  17 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Comment top

The crystal structure of (1,10-phenanthroline-N,N')tri(benzenepropanoic acid)lanthanum(III), (II), has previously been reported (Zhong et al., 2007). The crystal structure determination of the title compound, (I), has been carried out in order to elucidate the molecular conformation and to compare it with that of (II). We report herein the crystal structure of (I).

In the molecule of (I) (Fig. 1), the ligand bond lengths and angles are within normal ranges (Allen et al., 1987). The six-coordinate environment of the Nd atom is completed by the two N atoms of 1,10-phenanthroline ligand and four O atoms of three 3-phenylpropanoate ligands (Table 1). The Nd—O bond lengths are in the range 2.429 (5) to 2.898 (6) Å. The Nd—N bond lengths are in the range 2.729 (6) to 2.731 (6) Å. C—H···O non-classical hydrogen bonds between C—H groups of 1,10-phenanthroline or 3-phenylpropanoate and O atoms of neighbouring 3-phenylpropanoate molecules, with an average C···O distances of 3.217 (10) Å, generate a layered hydrogen-bonded network (Fig. 2 and Table 2). The non-classical hydrogen-bonding interactions link the mononuclear complex into a supramolecular network structure, as in (II). The both compounds, (I) and (II), are isostructural.

Related literature top

For a related structure, see: Zhong et al. (2007). For bond-length data, see: Allen et al. (1987).

Experimental top

Crystals of the title compound (I) were synthesized using hydrothermal method in a 23 ml Teflon-lined Parr bomb, which was then sealed. Neodymium (III) nitrate hexahydrate (219.1 mg, 0.5 mmol), phen (99 mg, 0.5 mmol), 3-phenylpropanoate (150.2 mg, 1 mmol) and distilled water (4 g) were placed into the bomb and sealed. The bomb was then heated under autogenous pressure up to 423 K over the course of 7 d and allowed to cool at room temperature for 24 h. Upon opening the bomb, a clear colourless solution was decanted from small colourless crystals. These crystals were washed with distilled water followed by ethanol, and allowed to air-dry at room temperature.

Structure description top

For a related structure, see: Zhong et al. (2007). For bond-length data, see: Allen et al. (1987).

Computing details top

Data collection: APEX2 (Bruker, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. View of the molecule of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A packing diagram of (I). Hydrogen bonds are shown as dashed lines.

(1,10-Phenanthroline-κ²N,N')tris(3-phenylpropanoato- κO)neodymium(III) top

Crystal data top

[Nd(C₉H₉O₂)₃(C₁₂H₈N₂)]	F(000) = 1564
M_r = 771.93	D_x = 1.461 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8997 reflections
a = 19.9971 (13) Å	θ = 2.5–26.5°
b = 8.7352 (14) Å	µ = 1.53 mm⁻¹
c = 20.9978 (12) Å	T = 273 K
β = 106.903 (8)°	Plane, colourless
V = 3509.4 (6) Å³	0.33 × 0.12 × 0.08 mm
Z = 4

Data collection top

Bruker APEXII area-detector diffractometer	6782 independent reflections
Radiation source: fine-focus sealed tube	4739 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
φ and ω scans	θ_max = 26.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −24→24
T_min = 0.632, T_max = 0.886	k = −10→10
25068 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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.188	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.1501P)² + 0.285P] where P = (F_o² + 2F_c²)/3
6782 reflections	(Δ/σ)_max = 0.002
373 parameters	Δρ_max = 1.39 e Å⁻³
4 restraints	Δρ_min = −1.12 e Å⁻³

Crystal data top

[Nd(C₉H₉O₂)₃(C₁₂H₈N₂)]	V = 3509.4 (6) Å³
M_r = 771.93	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 19.9971 (13) Å	µ = 1.53 mm⁻¹
b = 8.7352 (14) Å	T = 273 K
c = 20.9978 (12) Å	0.33 × 0.12 × 0.08 mm
β = 106.903 (8)°

Data collection top

Bruker APEXII area-detector diffractometer	6782 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4739 reflections with I > 2σ(I)
T_min = 0.632, T_max = 0.886	R_int = 0.041
25068 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	4 restraints
wR(F²) = 0.188	H-atom parameters constrained
S = 1.02	Δρ_max = 1.39 e Å⁻³
6782 reflections	Δρ_min = −1.12 e Å⁻³
373 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	0.931203 (18)	0.19073 (4)	0.964289 (16)	0.04101 (18)
O1	0.8463 (2)	−0.0366 (5)	0.9193 (2)	0.0471 (11)
O2	0.9471 (3)	−0.1386 (7)	0.9774 (2)	0.0533 (12)
O3	0.9709 (2)	0.0612 (6)	0.8749 (2)	0.0500 (11)
O4	1.0666 (3)	−0.0829 (6)	0.9216 (2)	0.0542 (12)
O5	0.9402 (2)	0.4211 (5)	1.0341 (2)	0.0504 (11)
O6	1.0077 (3)	0.6123 (6)	1.0912 (2)	0.0600 (14)
N1	0.7968 (3)	0.2347 (8)	0.9665 (3)	0.0513 (14)
N2	0.8347 (3)	0.3068 (6)	0.8547 (3)	0.0500 (15)
C1	0.7782 (5)	0.1907 (9)	1.0201 (5)	0.068 (2)
H1	0.8131	0.1682	1.0591	0.081*
C2	0.7094 (5)	0.1773 (12)	1.0197 (6)	0.090 (3)
H2	0.6979	0.1455	1.0574	0.108*
C3	0.6574 (5)	0.2131 (13)	0.9607 (7)	0.094 (4)
H3	0.6107	0.2056	0.9595	0.113*
C4	0.6742 (5)	0.2587 (14)	0.9054 (5)	0.083 (3)
C5	0.7466 (4)	0.2672 (9)	0.9098 (4)	0.0562 (19)
C6	0.6188 (6)	0.2947 (17)	0.8414 (8)	0.127 (6)
H6	0.5716	0.2846	0.8378	0.152*
C7	0.6419 (6)	0.3455 (15)	0.7860 (6)	0.103 (4)
H7	0.6091	0.3736	0.7464	0.124*
C8	0.7127 (5)	0.3530 (12)	0.7910 (4)	0.075 (3)
C9	0.7667 (4)	0.3100 (8)	0.8500 (4)	0.055 (2)
C10	0.7369 (7)	0.4016 (12)	0.7367 (5)	0.093 (3)
H10	0.7049	0.4326	0.6972	0.111*
C11	0.8055 (6)	0.4031 (12)	0.7421 (4)	0.084 (3)
H11	0.8215	0.4398	0.7075	0.101*
C12	0.8525 (5)	0.3482 (9)	0.8007 (4)	0.066 (2)
H12	0.8992	0.3401	0.8021	0.079*
C13	1.0280 (4)	0.0023 (8)	0.8771 (3)	0.0452 (15)
C14	1.0519 (4)	0.0502 (9)	0.8171 (3)	0.0515 (10)
H14A	1.0175	0.0179	0.7764	0.062*
H14B	1.0558	0.1608	0.8162	0.062*
C15	1.1170 (4)	−0.0168 (9)	0.8210 (3)	0.0515 (10)
H15A	1.1502	0.0165	0.8622	0.062*
H15B	1.1121	−0.1269	0.8239	0.062*
C16	1.1456 (4)	0.0136 (9)	0.7692 (3)	0.0515 (10)
C17	1.2069 (5)	−0.0570 (13)	0.7758 (5)	0.086 (3)
H17	1.2269	−0.1185	0.8125	0.103*
C18	1.2403 (6)	−0.0364 (15)	0.7261 (7)	0.099 (3)
H18	1.2830	−0.0833	0.7300	0.119*
C19	1.2092 (7)	0.0548 (14)	0.6709 (7)	0.115 (5)
H19	1.2313	0.0670	0.6379	0.139*
C20	1.1489 (8)	0.1242 (16)	0.6647 (6)	0.114 (4)
H20	1.1287	0.1832	0.6271	0.137*
C21	1.1142 (6)	0.1086 (13)	0.7161 (5)	0.089 (3)
H21	1.0728	0.1600	0.7136	0.107*
C22	0.9694 (4)	0.4984 (8)	1.0862 (3)	0.0468 (16)
C23	0.9485 (4)	0.4455 (8)	1.1469 (3)	0.0481 (9)
H23B	0.8987	0.4610	1.1389	0.058*
H23A	0.9579	0.3368	1.1536	0.058*
C24	0.9859 (4)	0.5271 (8)	1.2062 (3)	0.0481 (9)
H24A	1.0354	0.5150	1.2116	0.058*
H24B	0.9752	0.6351	1.1984	0.058*
C25	0.9743 (4)	0.4887 (8)	1.2652 (3)	0.0481 (9)
C26	0.9278 (5)	0.3793 (13)	1.2715 (4)	0.076 (3)
H26	0.9024	0.3238	1.2346	0.091*
C27	0.9187 (8)	0.3518 (18)	1.3335 (6)	0.119 (5)
H27	0.8874	0.2767	1.3378	0.143*
C28	0.9560 (6)	0.4354 (16)	1.3898 (5)	0.103 (4)
H28	0.9476	0.4197	1.4306	0.124*
C29	1.0051 (6)	0.5407 (13)	1.3840 (4)	0.094 (3)
H29	1.0317	0.5926	1.4215	0.113*
C30	1.0153 (5)	0.5704 (11)	1.3217 (4)	0.076 (2)
H30	1.0481	0.6420	1.3175	0.091*
C31	0.8831 (4)	−0.1523 (9)	0.9389 (3)	0.0471 (16)
C32	0.8573 (4)	−0.3127 (8)	0.9194 (4)	0.057 (2)
H32A	0.8755	−0.3463	0.8836	0.069*
H32B	0.8766	−0.3798	0.9571	0.069*
C33	0.7864 (7)	−0.3302 (12)	0.8992 (7)	0.1029 (15)
H33A	0.7670	−0.2563	0.8643	0.123*
H33B	0.7759	−0.4313	0.8798	0.123*
C34	0.7536 (7)	−0.3141 (9)	0.9460 (8)	0.1029 (15)
C35	0.7827 (7)	−0.2751 (13)	1.0104 (7)	0.1029 (15)
H35	0.8303	−0.2549	1.0265	0.123*
C36	0.7376 (6)	−0.2651 (14)	1.0551 (7)	0.1029 (15)
H36	0.7549	−0.2397	1.0999	0.123*
C37	0.6714 (7)	−0.2947 (12)	1.0267 (7)	0.1029 (15)
H37	0.6425	−0.2882	1.0541	0.123*
C38	0.6392 (7)	−0.3341 (12)	0.9616 (7)	0.1029 (15)
H38	0.5918	−0.3573	0.9464	0.123*
C39	0.6804 (7)	−0.3368 (12)	0.9214 (7)	0.1029 (15)
H39	0.6605	−0.3541	0.8761	0.123*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Nd1	0.0460 (3)	0.0368 (3)	0.0352 (2)	−0.00139 (14)	0.00398 (16)	0.00061 (13)
O1	0.043 (2)	0.039 (3)	0.051 (3)	−0.002 (2)	0.000 (2)	−0.003 (2)
O2	0.052 (3)	0.053 (3)	0.046 (3)	−0.002 (2)	0.001 (2)	0.007 (2)
O3	0.057 (3)	0.050 (3)	0.044 (3)	0.003 (2)	0.016 (2)	0.002 (2)
O4	0.062 (3)	0.057 (3)	0.045 (3)	0.007 (3)	0.018 (2)	0.013 (2)
O5	0.066 (3)	0.039 (3)	0.044 (3)	−0.002 (2)	0.013 (2)	−0.006 (2)
O6	0.083 (4)	0.058 (3)	0.040 (3)	−0.028 (3)	0.019 (2)	−0.001 (2)
N1	0.048 (3)	0.049 (4)	0.050 (4)	0.005 (3)	0.004 (3)	−0.006 (3)
N2	0.060 (4)	0.047 (4)	0.034 (3)	0.005 (3)	0.001 (3)	0.001 (2)
C1	0.058 (5)	0.085 (7)	0.060 (5)	0.011 (4)	0.016 (4)	−0.004 (4)
C2	0.055 (5)	0.131 (10)	0.087 (7)	−0.004 (5)	0.026 (5)	−0.015 (6)
C3	0.051 (5)	0.117 (10)	0.110 (10)	−0.009 (5)	0.018 (6)	−0.014 (7)
C4	0.054 (5)	0.094 (7)	0.083 (7)	0.005 (5)	−0.005 (5)	−0.022 (6)
C5	0.058 (4)	0.034 (4)	0.068 (5)	0.008 (3)	0.005 (4)	−0.007 (3)
C6	0.049 (6)	0.188 (17)	0.127 (12)	0.001 (7)	0.000 (7)	−0.022 (10)
C7	0.073 (7)	0.140 (10)	0.068 (7)	0.042 (6)	−0.023 (5)	0.005 (7)
C8	0.077 (6)	0.074 (6)	0.051 (5)	0.019 (5)	−0.017 (4)	−0.009 (4)
C9	0.063 (5)	0.041 (4)	0.046 (4)	0.002 (3)	−0.008 (4)	−0.007 (3)
C10	0.122 (9)	0.077 (7)	0.053 (6)	0.013 (6)	−0.017 (5)	−0.006 (5)
C11	0.116 (8)	0.085 (7)	0.037 (4)	0.001 (6)	0.001 (5)	0.012 (4)
C12	0.083 (6)	0.052 (5)	0.054 (5)	−0.003 (4)	0.007 (4)	0.009 (4)
C13	0.052 (4)	0.040 (4)	0.042 (4)	−0.008 (3)	0.010 (3)	−0.001 (3)
C14	0.055 (2)	0.057 (3)	0.046 (2)	0.006 (2)	0.0212 (19)	0.0120 (19)
C15	0.055 (2)	0.057 (3)	0.046 (2)	0.006 (2)	0.0212 (19)	0.0120 (19)
C16	0.055 (2)	0.057 (3)	0.046 (2)	0.006 (2)	0.0212 (19)	0.0120 (19)
C17	0.085 (6)	0.111 (8)	0.073 (6)	0.006 (6)	0.042 (5)	−0.003 (6)
C18	0.086 (7)	0.114 (10)	0.111 (9)	−0.011 (7)	0.051 (7)	−0.011 (7)
C19	0.147 (11)	0.089 (8)	0.157 (12)	−0.016 (8)	0.118 (10)	−0.005 (8)
C20	0.163 (12)	0.110 (9)	0.098 (9)	0.018 (9)	0.083 (9)	0.036 (7)
C21	0.109 (8)	0.089 (7)	0.091 (7)	0.001 (6)	0.064 (6)	0.018 (6)
C22	0.057 (4)	0.035 (4)	0.046 (4)	0.000 (3)	0.013 (3)	0.001 (3)
C23	0.066 (2)	0.046 (2)	0.0334 (19)	−0.0147 (19)	0.0161 (17)	−0.0033 (16)
C24	0.066 (2)	0.046 (2)	0.0334 (19)	−0.0147 (19)	0.0161 (17)	−0.0033 (16)
C25	0.066 (2)	0.046 (2)	0.0334 (19)	−0.0147 (19)	0.0161 (17)	−0.0033 (16)
C26	0.075 (6)	0.103 (7)	0.051 (5)	−0.034 (5)	0.019 (4)	−0.010 (5)
C27	0.144 (11)	0.157 (11)	0.073 (7)	−0.058 (10)	0.058 (8)	−0.003 (8)
C28	0.124 (9)	0.140 (11)	0.056 (6)	−0.017 (8)	0.041 (6)	0.008 (6)
C29	0.125 (9)	0.107 (8)	0.046 (5)	−0.012 (7)	0.017 (5)	−0.004 (5)
C30	0.084 (6)	0.083 (6)	0.056 (5)	−0.028 (5)	0.014 (4)	−0.012 (4)
C31	0.047 (4)	0.056 (4)	0.034 (3)	−0.001 (3)	0.005 (3)	−0.002 (3)
C32	0.053 (4)	0.059 (5)	0.053 (5)	0.006 (3)	0.004 (4)	−0.008 (3)
C33	0.103 (3)	0.083 (3)	0.130 (4)	0.001 (3)	0.044 (3)	0.018 (3)
C34	0.103 (3)	0.083 (3)	0.130 (4)	0.001 (3)	0.044 (3)	0.018 (3)
C35	0.103 (3)	0.083 (3)	0.130 (4)	0.001 (3)	0.044 (3)	0.018 (3)
C36	0.103 (3)	0.083 (3)	0.130 (4)	0.001 (3)	0.044 (3)	0.018 (3)
C37	0.103 (3)	0.083 (3)	0.130 (4)	0.001 (3)	0.044 (3)	0.018 (3)
C38	0.103 (3)	0.083 (3)	0.130 (4)	0.001 (3)	0.044 (3)	0.018 (3)
C39	0.103 (3)	0.083 (3)	0.130 (4)	0.001 (3)	0.044 (3)	0.018 (3)

Geometric parameters (Å, º) top

Nd1—O1	2.606 (4)	C15—H15B	0.9700
Nd1—O2	2.898 (6)	C16—C17	1.344 (11)
Nd1—O2ⁱ	2.429 (5)	C16—C21	1.385 (12)
Nd1—O3	2.511 (5)	C17—C18	1.403 (14)
Nd1—O4ⁱ	2.563 (4)	C17—H17	0.9300
Nd1—O5	2.465 (5)	C18—C19	1.395 (17)
Nd1—O6ⁱⁱ	2.576 (5)	C18—H18	0.9300
Nd1—N1	2.729 (6)	C19—C20	1.320 (16)
Nd1—N2	2.731 (6)	C19—H19	0.9300
O1—C31	1.248 (9)	C20—C21	1.450 (13)
O2—C31	1.305 (8)	C20—H20	0.9300
O2—Nd1ⁱ	2.429 (5)	C21—H21	0.9300
O3—C13	1.241 (8)	C22—C23	1.525 (9)
O4—C13	1.266 (8)	C23—C24	1.440 (9)
O4—Nd1ⁱ	2.563 (4)	C23—H23B	0.9700
O5—C22	1.273 (8)	C23—H23A	0.9700
O6—C22	1.241 (8)	C24—C25	1.366 (9)
O6—Nd1ⁱⁱ	2.576 (5)	C24—H24A	0.9700
N1—C1	1.339 (11)	C24—H24B	0.9700
N1—C5	1.346 (9)	C25—C26	1.368 (11)
N2—C12	1.333 (10)	C25—C30	1.422 (10)
N2—C9	1.337 (10)	C26—C27	1.385 (13)
C1—C2	1.378 (12)	C26—H26	0.9300
C1—H1	0.9300	C27—C28	1.406 (16)
C2—C3	1.401 (16)	C27—H27	0.9300
C2—H2	0.9300	C28—C29	1.378 (15)
C3—C4	1.359 (16)	C28—H28	0.9300
C3—H3	0.9300	C29—C30	1.405 (12)
C4—C5	1.426 (12)	C29—H29	0.9300
C4—C6	1.505 (16)	C30—H30	0.9300
C5—C9	1.473 (12)	C31—C32	1.508 (10)
C6—C7	1.442 (18)	C32—C33	1.364 (14)
C6—H6	0.9300	C32—H32A	0.9700
C7—C8	1.390 (15)	C32—H32B	0.9700
C7—H7	0.9300	C33—C34	1.337 (17)
C8—C10	1.426 (15)	C33—H33A	0.9700
C8—C9	1.436 (11)	C33—H33B	0.9700
C10—C11	1.344 (14)	C34—C35	1.352 (19)
C10—H10	0.9300	C34—C39	1.418 (18)
C11—C12	1.398 (12)	C35—C36	1.482 (17)
C11—H11	0.9300	C35—H35	0.9300
C12—H12	0.9300	C36—C37	1.309 (17)
C13—C14	1.529 (9)	C36—H36	0.9300
C14—C15	1.408 (9)	C37—C38	1.374 (18)
C14—H14A	0.9700	C37—H37	0.9300
C14—H14B	0.9700	C38—C39	1.342 (16)
C15—C16	1.393 (9)	C38—H38	0.9300
C15—H15A	0.9700	C39—H39	0.9300

O1—Nd1—O2	47.14 (14)	C13—C14—H14B	109.6
O1—Nd1—O3	72.53 (15)	H14A—C14—H14B	108.2
O1—Nd1—O5	139.94 (16)	C16—C15—C14	117.3 (6)
O2—Nd1—O3	64.78 (15)	C16—C15—H15A	108.0
O2—Nd1—O5	140.06 (14)	C14—C15—H15A	108.0
O3—Nd1—O5	145.90 (16)	C16—C15—H15B	108.0
O1—Nd1—N1	64.66 (17)	C14—C15—H15B	108.0
O2—Nd1—N1	102.65 (17)	H15A—C15—H15B	107.2
O3—Nd1—N1	127.13 (17)	C17—C16—C21	122.9 (8)
O5—Nd1—N1	77.14 (17)	C17—C16—C15	113.7 (7)
O1—Nd1—N2	75.58 (16)	C21—C16—C15	123.4 (7)
O2—Nd1—N2	118.64 (15)	C16—C17—C18	118.8 (10)
O3—Nd1—N2	80.61 (17)	C16—C17—H17	120.6
O5—Nd1—N2	96.29 (16)	C18—C17—H17	120.6
N1—Nd1—N2	60.29 (19)	C19—C18—C17	119.8 (11)
O2ⁱ—Nd1—O5	87.93 (18)	C19—C18—H18	120.1
O2ⁱ—Nd1—O3	78.68 (16)	C17—C18—H18	120.1
O2ⁱ—Nd1—O4ⁱ	73.59 (16)	C20—C19—C18	121.3 (10)
O5—Nd1—O4ⁱ	76.45 (16)	C20—C19—H19	119.4
O3—Nd1—O4ⁱ	127.61 (16)	C18—C19—H19	119.4
O2ⁱ—Nd1—O6ⁱⁱ	79.37 (18)	C19—C20—C21	120.2 (12)
O5—Nd1—O6ⁱⁱ	76.17 (16)	C19—C20—H20	119.9
O3—Nd1—O6ⁱⁱ	70.63 (16)	C21—C20—H20	119.9
O4ⁱ—Nd1—O6ⁱⁱ	141.85 (16)	C16—C21—C20	117.0 (10)
O2ⁱ—Nd1—O1	119.47 (18)	C16—C21—H21	121.5
O4ⁱ—Nd1—O1	83.77 (16)	C20—C21—H21	121.5
O6ⁱⁱ—Nd1—O1	133.62 (15)	O6—C22—O5	127.9 (6)
O2ⁱ—Nd1—N1	149.95 (17)	O6—C22—C23	119.0 (6)
O4ⁱ—Nd1—N1	77.58 (17)	O5—C22—C23	112.9 (6)
O6ⁱⁱ—Nd1—N1	120.85 (19)	C24—C23—C22	111.9 (6)
O2ⁱ—Nd1—N2	148.54 (18)	C24—C23—H23B	109.2
O4ⁱ—Nd1—N2	137.72 (18)	C22—C23—H23B	109.2
O6ⁱⁱ—Nd1—N2	71.52 (18)	C24—C23—H23A	109.2
O2ⁱ—Nd1—O2	72.54 (19)	C22—C23—H23A	109.2
O4ⁱ—Nd1—O2	64.85 (15)	H23B—C23—H23A	107.9
O6ⁱⁱ—Nd1—O2	130.74 (16)	C25—C24—C23	118.7 (6)
C31—O1—Nd1	103.7 (4)	C25—C24—H24A	107.6
C31—O2—Nd1ⁱ	162.4 (5)	C23—C24—H24A	107.6
C31—O2—Nd1	88.4 (4)	C25—C24—H24B	107.6
Nd1ⁱ—O2—Nd1	107.46 (19)	C23—C24—H24B	107.6
C13—O3—Nd1	130.3 (4)	H24A—C24—H24B	107.1
C13—O4—Nd1ⁱ	138.3 (4)	C24—C25—C26	124.0 (6)
C22—O5—Nd1	151.6 (5)	C24—C25—C30	115.2 (7)
C22—O6—Nd1ⁱⁱ	149.2 (4)	C26—C25—C30	120.8 (7)
C1—N1—C5	119.1 (7)	C25—C26—C27	119.4 (9)
C1—N1—Nd1	119.3 (5)	C25—C26—H26	120.3
C5—N1—Nd1	120.0 (5)	C27—C26—H26	120.3
C12—N2—C9	116.7 (7)	C26—C27—C28	121.2 (10)
C12—N2—Nd1	121.4 (5)	C26—C27—H27	119.4
C9—N2—Nd1	121.7 (5)	C28—C27—H27	119.4
N1—C1—C2	122.6 (9)	C29—C28—C27	119.3 (9)
N1—C1—H1	118.7	C29—C28—H28	120.4
C2—C1—H1	118.7	C27—C28—H28	120.4
C1—C2—C3	118.0 (10)	C28—C29—C30	120.4 (9)
C1—C2—H2	121.0	C28—C29—H29	119.8
C3—C2—H2	121.0	C30—C29—H29	119.8
C4—C3—C2	121.1 (9)	C29—C30—C25	118.7 (8)
C4—C3—H3	119.5	C29—C30—H30	120.6
C2—C3—H3	119.5	C25—C30—H30	120.6
C3—C4—C5	117.3 (9)	O1—C31—O2	120.5 (7)
C3—C4—C6	121.6 (10)	O1—C31—C32	122.7 (6)
C5—C4—C6	121.1 (11)	O2—C31—C32	116.8 (7)
N1—C5—C4	121.9 (8)	C33—C32—C31	115.5 (7)
N1—C5—C9	119.3 (7)	C33—C32—H32A	108.4
C4—C5—C9	118.8 (8)	C31—C32—H32A	108.4
C7—C6—C4	117.4 (10)	C33—C32—H32B	108.4
C7—C6—H6	121.3	C31—C32—H32B	108.4
C4—C6—H6	121.3	H32A—C32—H32B	107.5
C8—C7—C6	120.8 (9)	C34—C33—C32	116.6 (13)
C8—C7—H7	119.6	C34—C33—H33A	108.1
C6—C7—H7	119.6	C32—C33—H33A	108.1
C7—C8—C10	121.9 (9)	C34—C33—H33B	108.1
C7—C8—C9	123.1 (10)	C32—C33—H33B	108.1
C10—C8—C9	115.0 (9)	H33A—C33—H33B	107.3
N2—C9—C8	124.2 (8)	C33—C34—C35	127.0 (14)
N2—C9—C5	117.1 (6)	C33—C34—C39	113.1 (15)
C8—C9—C5	118.6 (8)	C35—C34—C39	119.9 (13)
C11—C10—C8	120.8 (9)	C34—C35—C36	119.0 (13)
C11—C10—H10	119.6	C34—C35—H35	120.5
C8—C10—H10	119.6	C36—C35—H35	120.5
C10—C11—C12	118.5 (9)	C37—C36—C35	114.8 (14)
C10—C11—H11	120.7	C37—C36—H36	122.6
C12—C11—H11	120.7	C35—C36—H36	122.6
N2—C12—C11	124.5 (9)	C36—C37—C38	128.5 (14)
N2—C12—H12	117.8	C36—C37—H37	115.7
C11—C12—H12	117.8	C38—C37—H37	115.7
O3—C13—O4	128.9 (6)	C39—C38—C37	115.7 (13)
O3—C13—C14	111.1 (6)	C39—C38—H38	122.2
O4—C13—C14	120.0 (6)	C37—C38—H38	122.2
C15—C14—C13	110.1 (6)	C38—C39—C34	121.8 (15)
C15—C14—H14A	109.6	C38—C39—H39	119.1
C13—C14—H14A	109.6	C34—C39—H39	119.1
C15—C14—H14B	109.6

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O4ⁱ	0.93	2.44	3.132 (10)	132
C12—H12···O6ⁱⁱ	0.93	2.50	3.066 (10)	119
C32—H32B···O5ⁱⁱⁱ	0.97	2.46	3.411 (9)	165
C10—H10···O1^iv	0.93	2.38	3.259 (10)	158

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

Experimental details

Crystal data
Chemical formula	[Nd(C₉H₉O₂)₃(C₁₂H₈N₂)]
M_r	771.93
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	273
a, b, c (Å)	19.9971 (13), 8.7352 (14), 20.9978 (12)
β (°)	106.903 (8)
V (Å³)	3509.4 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.53
Crystal size (mm)	0.33 × 0.12 × 0.08

Data collection
Diffractometer	Bruker APEXII area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.632, 0.886
No. of measured, independent and observed [I > 2σ(I)] reflections	25068, 6782, 4739
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.188, 1.02
No. of reflections	6782
No. of parameters	373
No. of restraints	4
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.39, −1.12

Computer programs: APEX2 (Bruker, 1996), SAINT (Siemens, 1996), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Siemens, 1996), SHELXTL.

Selected geometric parameters (Å, º) top

Nd1—O1	2.606 (4)	Nd1—O5	2.465 (5)
Nd1—O2	2.898 (6)	Nd1—O6ⁱⁱ	2.576 (5)
Nd1—O2ⁱ	2.429 (5)	Nd1—N1	2.729 (6)
Nd1—O3	2.511 (5)	Nd1—N2	2.731 (6)
Nd1—O4ⁱ	2.563 (4)

O1—Nd1—O2	47.14 (14)	O3—Nd1—N1	127.13 (17)
O1—Nd1—O3	72.53 (15)	O5—Nd1—N1	77.14 (17)
O1—Nd1—O5	139.94 (16)	O1—Nd1—N2	75.58 (16)
O2—Nd1—O3	64.78 (15)	O2—Nd1—N2	118.64 (15)
O2—Nd1—O5	140.06 (14)	O3—Nd1—N2	80.61 (17)
O3—Nd1—O5	145.90 (16)	O5—Nd1—N2	96.29 (16)
O1—Nd1—N1	64.66 (17)	N1—Nd1—N2	60.29 (19)
O2—Nd1—N1	102.65 (17)