Retracted: (1,10-Phenanthroline-κ²N,N′)tris­(phenoxyacetato)-κO;κO;κO,O′-neodymium(III)

In the mol­ecule of the title compound, [Nd(C₈H₇O₃)₃(C₁₂H₈N₂)], the Nd^III atom is six-coordinated by two N atoms of the 1,10-phenanthroline (phen) ligand and four O atoms of the three phenoxy­acetate ligands. In the crystal structure, inter­molecular C—H...O hydrogen bonds lead to a supra­molecular network.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.011 Å
• R factor = 0.041
• wR factor = 0.112
• Data-to-parameter ratio = 17.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.91 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C6
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C25
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C31
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         O9
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist.   C15    -C20           1.37 Ang.
PLAT335_ALERT_2_C Large Benzene C-C Range .......  C4     -C6            0.16 Ang.
PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...         11
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .      73.00 A   3 

Alert level G
PLAT794_ALERT_5_G Check Predicted Bond Valency for Nd1         (3)       2.88
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          3

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   8 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

---

S1. Comment

The crystal structure of tri(phenoxyacetic acid)(1,10-phenanthroline-N,N') cerium(III), (II), has recently 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 two N atoms of the 1,10-phenanthroline (phen) ligand and four O atoms of the three phenoxyacetic acid ligand (Table 1). The Nd—O and Nd—N bonds are in the range of [2.412 (3)–2.818 (4) Å] and [2.718 (4)–2.743 (4) Å], respectively (Table 1).

In the crystal structure, intermolecular C—H···O hydrogen bonds (Table 2) lead to a supramolecular network structure (Fig. 2), as in (II), in which they may be effective in the stabilization of the structure.

The both compounds, (I) and (II), are isostructural.

Related literature

For general background, see: Allen et al. (1987). For a related structure, see: Zhong et al. (2007).

S2. Experimental

Crystals of the title compound were synthesized using hydrothermal method in a 23 ml Teflon-lined Parr bomb. Neodymium (III) chloride hexahydrate (107.3 mg, 0.3 mmol), phen (59.4 mg, 0.3 mmol), phenoxyacetic acid (91.3 mg, 0.6 mmol) and distilled water (3 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 colorless solution was decanted from small colorless crystals, which were washed with distilled water followed by ethanol, and allowed to air-dry at room temperature.

S3. Refinement

H atoms were positioned geometrically, with C—H = 0.93 and 0.97 Å for aromatic and methylene H atoms, and constrained to ride on their parent atoms, with U_iso(H) = 1.2U_eq(C).

Computing details

Data collection: SMART (Siemens, 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

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A packing diagram for (I). Hydrogen bonds are shown as dashed lines.

(1,10-Phenanthroline-κ²N,N')tris(phenoxyacetato)-κO;κO;κO,O'- neodymium(III)

Crystal data

[Nd(C8H7O3)3(C12H8N2)]	F(000) = 1564
Mr = 777.85	Dx = 1.520 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9077 reflections
a = 20.103 (5) Å	θ = 2.5–27.0°
b = 8.5028 (17) Å	µ = 1.59 mm^−1
c = 20.7887 (14) Å	T = 273 K
β = 106.997 (4)°	Block, colorless
V = 3398.3 (11) Å^3	0.33 × 0.13 × 0.08 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	6951 independent reflections
Radiation source: fine-focus sealed tube	4794 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
φ and ω scans	θmax = 26.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −25→24
Tmin = 0.626, Tmax = 0.885	k = −10→10
25585 measured reflections	l = −26→25

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.112	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0646P)^2 + 0.9706P] where P = (Fo^2 + 2Fc^2)/3
6951 reflections	(Δ/σ)max = 0.002
403 parameters	Δρmax = 1.04 e Å^−3
3 restraints	Δρmin = −0.63 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Nd1	0.931203 (12)	0.19066 (3)	0.964281 (11)	0.03943 (10)
O1	0.97063 (16)	0.0607 (4)	0.87482 (14)	0.0468 (7)
O2	0.93999 (16)	0.4207 (3)	1.03415 (14)	0.0474 (7)
O3	0.84628 (14)	−0.0359 (3)	0.91886 (14)	0.0439 (7)
O4	0.94655 (15)	−0.1382 (4)	0.97728 (15)	0.0497 (8)
O5	1.06695 (16)	−0.0827 (4)	0.92164 (14)	0.0495 (8)
O6	1.00778 (18)	0.6127 (4)	1.09087 (15)	0.0567 (9)
O7	1.11832 (18)	−0.0166 (4)	0.82194 (17)	0.0667 (10)
O8	0.98695 (18)	0.5275 (4)	1.20633 (15)	0.0617 (9)
O9	0.78466 (18)	−0.3261 (4)	0.89805 (19)	0.0627 (10)
N1	0.79683 (19)	0.2343 (5)	0.9669 (2)	0.0476 (9)
N2	0.8341 (2)	0.3069 (4)	0.85460 (18)	0.0482 (9)
C1	0.7784 (3)	0.1918 (6)	1.0198 (3)	0.0635 (14)
H1	0.8131	0.1688	1.0593	0.076*
C2	0.7093 (3)	0.1795 (8)	1.0198 (4)	0.0833 (19)
H2	0.6978	0.1502	1.0583	0.100*
C3	0.6583 (3)	0.2123 (9)	0.9604 (4)	0.093 (2)
H3	0.6118	0.2026	0.9588	0.111*
C4	0.6745 (3)	0.2577 (8)	0.9049 (3)	0.0744 (17)
C5	0.7462 (3)	0.2674 (6)	0.9088 (3)	0.0527 (12)
C6	0.6227 (4)	0.2962 (10)	0.8401 (4)	0.109 (3)
H6	0.5755	0.2863	0.8360	0.131*
C7	0.6420 (4)	0.3441 (10)	0.7881 (4)	0.104 (3)
H7	0.6080	0.3721	0.7488	0.125*
C8	0.7134 (3)	0.3546 (7)	0.7900 (3)	0.0707 (17)
C9	0.7662 (3)	0.3100 (5)	0.8510 (2)	0.0519 (12)
C10	0.7358 (4)	0.4037 (8)	0.7368 (3)	0.087 (2)
H10	0.7036	0.4389	0.6976	0.105*
C11	0.8038 (4)	0.4014 (7)	0.7409 (3)	0.0795 (18)
H11	0.8187	0.4337	0.7046	0.095*
C12	0.8526 (3)	0.3493 (6)	0.8011 (2)	0.0626 (14)
H12	0.8993	0.3447	0.8030	0.075*
C13	1.0286 (2)	0.0034 (5)	0.8772 (2)	0.0427 (10)
C14	1.0524 (3)	0.0512 (6)	0.8173 (2)	0.0549 (12)
H14A	1.0186	0.0165	0.7761	0.066*
H14B	1.0557	0.1649	0.8157	0.066*
C15	1.1459 (3)	0.0143 (7)	0.7703 (3)	0.0625 (14)
C16	1.2078 (3)	−0.0571 (8)	0.7766 (3)	0.0792 (17)
H16	1.2284	−0.1192	0.8139	0.095*
C17	1.2402 (4)	−0.0364 (9)	0.7267 (4)	0.094 (2)
H17	1.2829	−0.0841	0.7307	0.113*
C18	1.2100 (5)	0.0526 (9)	0.6724 (4)	0.103 (3)
H18	1.2320	0.0648	0.6390	0.124*
C19	1.1488 (5)	0.1241 (10)	0.6655 (4)	0.107 (3)
H19	1.1286	0.1852	0.6277	0.129*
C20	1.1150 (4)	0.1061 (8)	0.7159 (3)	0.0832 (19)
H20	1.0728	0.1556	0.7120	0.100*
C21	0.9694 (2)	0.4987 (5)	1.0865 (2)	0.0438 (10)
C22	0.9488 (3)	0.4453 (6)	1.1474 (2)	0.0554 (12)
H22A	0.8994	0.4632	1.1397	0.066*
H22B	0.9574	0.3333	1.1540	0.066*
C23	0.9745 (3)	0.4892 (6)	1.2653 (2)	0.0550 (12)
C24	0.9277 (3)	0.3802 (8)	1.2720 (3)	0.0724 (16)
H24	0.9013	0.3251	1.2345	0.087*
C25	0.9193 (4)	0.3515 (10)	1.3342 (3)	0.105 (3)
H25	0.8878	0.2752	1.3388	0.126*
C26	0.9568 (4)	0.4343 (10)	1.3899 (3)	0.103 (2)
H26	0.9496	0.4169	1.4315	0.123*
C27	1.0044 (4)	0.5414 (9)	1.3836 (3)	0.089 (2)
H27	1.0306	0.5959	1.4213	0.107*
C28	1.0143 (3)	0.5704 (7)	1.3218 (3)	0.0712 (15)
H28	1.0472	0.6436	1.3178	0.085*
C29	0.8838 (2)	−0.1507 (6)	0.9391 (2)	0.0445 (11)
C30	0.8574 (3)	−0.3145 (5)	0.9194 (3)	0.0557 (12)
H30A	0.8753	−0.3508	0.8835	0.067*
H30B	0.8754	−0.3839	0.9576	0.067*
C31	0.7525 (6)	−0.3138 (9)	0.9448 (6)	0.1243 (14)
C32	0.7840 (5)	−0.2778 (9)	1.0118 (6)	0.1243 (14)
H32	0.8316	−0.2608	1.0285	0.149*
C33	0.7406 (5)	−0.2683 (9)	1.0529 (6)	0.1243 (14)
H33	0.7595	−0.2444	1.0983	0.149*
C34	0.6740 (5)	−0.2923 (9)	1.0290 (6)	0.1243 (14)
H34	0.6474	−0.2803	1.0585	0.149*
C35	0.6393 (5)	−0.3341 (9)	0.9635 (5)	0.1243 (14)
H35	0.5920	−0.3572	0.9496	0.149*
C36	0.6802 (5)	−0.3391 (9)	0.9200 (5)	0.1243 (14)
H36	0.6598	−0.3592	0.8745	0.149*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Nd1	0.04609 (15)	0.03354 (15)	0.03390 (14)	−0.00157 (11)	0.00426 (9)	0.00058 (10)
O1	0.0562 (19)	0.0452 (19)	0.0387 (16)	0.0066 (16)	0.0134 (14)	0.0014 (14)
O2	0.068 (2)	0.0318 (16)	0.0408 (17)	−0.0052 (15)	0.0138 (14)	−0.0046 (13)
O3	0.0444 (16)	0.0331 (17)	0.0466 (17)	0.0008 (14)	0.0015 (13)	−0.0033 (13)
O4	0.0462 (18)	0.0494 (19)	0.0449 (18)	−0.0033 (15)	0.0000 (14)	0.0073 (14)
O5	0.0603 (19)	0.0485 (19)	0.0409 (17)	0.0073 (16)	0.0166 (14)	0.0100 (15)
O6	0.084 (2)	0.048 (2)	0.0386 (17)	−0.0261 (19)	0.0183 (16)	−0.0031 (15)
O7	0.068 (2)	0.083 (3)	0.057 (2)	0.017 (2)	0.0291 (18)	0.0200 (19)
O8	0.087 (2)	0.060 (2)	0.0387 (18)	−0.0270 (19)	0.0193 (17)	−0.0062 (15)
O9	0.058 (2)	0.045 (2)	0.072 (2)	−0.0135 (16)	−0.0015 (18)	−0.0068 (17)
N1	0.047 (2)	0.040 (2)	0.048 (2)	0.0041 (17)	0.0034 (18)	−0.0080 (17)
N2	0.061 (2)	0.036 (2)	0.038 (2)	0.0031 (18)	−0.0008 (17)	0.0002 (16)
C1	0.057 (3)	0.073 (4)	0.059 (3)	0.008 (3)	0.015 (3)	−0.002 (3)
C2	0.057 (3)	0.112 (6)	0.086 (5)	0.003 (3)	0.029 (3)	−0.013 (4)
C3	0.048 (3)	0.105 (6)	0.121 (6)	−0.004 (3)	0.020 (4)	−0.017 (5)
C4	0.052 (3)	0.084 (4)	0.073 (4)	0.006 (3)	−0.003 (3)	−0.018 (3)
C5	0.051 (3)	0.036 (3)	0.062 (3)	0.007 (2)	0.001 (2)	−0.011 (2)
C6	0.061 (4)	0.139 (8)	0.102 (6)	0.016 (4)	−0.018 (4)	−0.030 (6)
C7	0.079 (5)	0.109 (6)	0.087 (5)	0.038 (4)	−0.034 (4)	−0.022 (5)
C8	0.074 (4)	0.061 (3)	0.053 (3)	0.018 (3)	−0.018 (3)	−0.011 (3)
C9	0.059 (3)	0.034 (3)	0.046 (3)	0.006 (2)	−0.011 (2)	−0.004 (2)
C10	0.119 (6)	0.068 (4)	0.046 (3)	0.018 (4)	−0.021 (3)	0.001 (3)
C11	0.117 (5)	0.071 (4)	0.038 (3)	−0.002 (4)	0.003 (3)	0.011 (3)
C12	0.080 (4)	0.051 (3)	0.047 (3)	−0.002 (3)	0.005 (3)	0.008 (2)
C13	0.056 (3)	0.033 (2)	0.037 (2)	−0.007 (2)	0.011 (2)	−0.0030 (19)
C14	0.064 (3)	0.056 (3)	0.047 (3)	0.005 (3)	0.019 (2)	0.011 (2)
C15	0.070 (3)	0.067 (4)	0.059 (3)	−0.008 (3)	0.033 (3)	0.001 (3)
C16	0.079 (4)	0.096 (5)	0.073 (4)	0.002 (4)	0.037 (3)	−0.002 (4)
C17	0.092 (5)	0.097 (6)	0.113 (6)	−0.006 (4)	0.062 (4)	−0.008 (5)
C18	0.138 (7)	0.083 (5)	0.126 (7)	−0.017 (5)	0.096 (6)	−0.005 (5)
C19	0.156 (7)	0.101 (5)	0.091 (5)	0.010 (6)	0.077 (5)	0.027 (4)
C20	0.100 (5)	0.089 (5)	0.078 (4)	0.007 (4)	0.053 (4)	0.023 (4)
C21	0.058 (3)	0.034 (2)	0.038 (2)	−0.001 (2)	0.013 (2)	0.0013 (19)
C22	0.074 (3)	0.051 (3)	0.043 (3)	−0.018 (3)	0.019 (2)	−0.004 (2)
C23	0.073 (3)	0.054 (3)	0.037 (3)	−0.002 (3)	0.015 (2)	0.003 (2)
C24	0.078 (4)	0.088 (4)	0.053 (3)	−0.033 (3)	0.022 (3)	−0.004 (3)
C25	0.127 (6)	0.134 (7)	0.067 (4)	−0.056 (5)	0.048 (4)	−0.003 (4)
C26	0.126 (6)	0.140 (7)	0.051 (4)	−0.026 (5)	0.040 (4)	0.009 (4)
C27	0.117 (5)	0.104 (5)	0.041 (3)	−0.021 (4)	0.013 (3)	−0.010 (3)
C28	0.086 (4)	0.073 (4)	0.051 (3)	−0.020 (3)	0.016 (3)	−0.011 (3)
C29	0.048 (3)	0.049 (3)	0.032 (2)	−0.006 (2)	0.0055 (19)	−0.0039 (19)
C30	0.061 (3)	0.043 (3)	0.056 (3)	0.002 (2)	0.008 (2)	−0.007 (2)
C31	0.136 (3)	0.086 (2)	0.173 (4)	0.014 (2)	0.080 (3)	0.027 (3)
C32	0.136 (3)	0.086 (2)	0.173 (4)	0.014 (2)	0.080 (3)	0.027 (3)
C33	0.136 (3)	0.086 (2)	0.173 (4)	0.014 (2)	0.080 (3)	0.027 (3)
C34	0.136 (3)	0.086 (2)	0.173 (4)	0.014 (2)	0.080 (3)	0.027 (3)
C35	0.136 (3)	0.086 (2)	0.173 (4)	0.014 (2)	0.080 (3)	0.027 (3)
C36	0.136 (3)	0.086 (2)	0.173 (4)	0.014 (2)	0.080 (3)	0.027 (3)

Geometric parameters (Å, º)

Nd1—O1	2.484 (3)	C11—C12	1.416 (7)
Nd1—O2	2.412 (3)	C11—H11	0.9300
Nd1—O3	2.564 (3)	C12—H12	0.9300
Nd1—O4	2.818 (4)	C13—C14	1.515 (6)
Nd1—N1	2.743 (4)	C14—H14A	0.9700
Nd1—N2	2.718 (4)	C14—H14B	0.9700
Nd1—O4^i	2.443 (3)	C15—C16	1.358 (8)
Nd1—O5^i	2.533 (3)	C15—C20	1.366 (8)
Nd1—O6^ii	2.537 (3)	C16—C17	1.387 (8)
O1—C13	1.251 (5)	C16—H16	0.9300
O2—C21	1.264 (5)	C17—C18	1.347 (10)
O3—C29	1.231 (5)	C17—H17	0.9300
O4—C29	1.282 (5)	C18—C19	1.343 (10)
O4—Nd1^i	2.443 (3)	C18—H18	0.9300
O5—C13	1.252 (5)	C19—C20	1.413 (8)
O5—Nd1^i	2.533 (3)	C19—H19	0.9300
O6—C21	1.225 (5)	C20—H20	0.9300
O6—Nd1^ii	2.537 (3)	C21—C22	1.513 (6)
O7—C15	1.369 (6)	C22—H22A	0.9700
O7—C14	1.422 (6)	C22—H22B	0.9700
O8—C23	1.361 (5)	C23—C24	1.357 (7)
O8—C22	1.424 (5)	C23—C28	1.395 (7)
O9—C31	1.318 (10)	C24—C25	1.375 (8)
O9—C30	1.401 (6)	C24—H24	0.9300
N1—C1	1.310 (6)	C25—C26	1.376 (9)
N1—C5	1.362 (6)	C25—H25	0.9300
N2—C12	1.322 (6)	C26—C27	1.354 (9)
N2—C9	1.345 (6)	C26—H26	0.9300
C1—C2	1.394 (8)	C27—C28	1.379 (8)
C1—H1	0.9300	C27—H27	0.9300
C2—C3	1.383 (10)	C28—H28	0.9300
C2—H2	0.9300	C29—C30	1.505 (6)
C3—C4	1.344 (9)	C30—H30A	0.9700
C3—H3	0.9300	C30—H30B	0.9700
C4—C5	1.422 (8)	C31—C32	1.386 (14)
C4—C6	1.479 (9)	C31—C36	1.410 (13)
C5—C9	1.421 (7)	C32—C33	1.390 (11)
C6—C7	1.316 (11)	C32—H32	0.9300
C6—H6	0.9300	C33—C34	1.300 (12)
C7—C8	1.427 (10)	C33—H33	0.9300
C7—H7	0.9300	C34—C35	1.383 (13)
C8—C10	1.375 (9)	C34—H34	0.9300
C8—C9	1.446 (6)	C35—C36	1.388 (11)
C10—C11	1.346 (9)	C35—H35	0.9300
C10—H10	0.9300	C36—H36	0.9300
O1—Nd1—O2	145.95 (10)	C12—C11—H11	120.4
O1—Nd1—O3	73.37 (10)	N2—C12—C11	122.5 (6)
O1—Nd1—O4	65.19 (9)	N2—C12—H12	118.8
O2—Nd1—O3	139.00 (10)	C11—C12—H12	118.8
O2—Nd1—O4	139.50 (9)	O1—C13—O5	128.5 (4)
O3—Nd1—O4	48.10 (9)	O1—C13—C14	112.2 (4)
O1—Nd1—N1	127.33 (11)	O5—C13—C14	119.3 (4)
O2—Nd1—N1	77.16 (11)	O7—C14—C13	110.3 (4)
O3—Nd1—N1	63.59 (11)	O7—C14—H14A	109.6
O4—Nd1—N1	102.31 (10)	C13—C14—H14A	109.6
O1—Nd1—N2	80.90 (11)	O7—C14—H14B	109.6
O2—Nd1—N2	96.80 (10)	C13—C14—H14B	109.6
O3—Nd1—N2	74.13 (10)	H14A—C14—H14B	108.1
O4—Nd1—N2	118.24 (10)	C16—C15—C20	121.1 (5)
N1—Nd1—N2	59.81 (12)	C16—C15—O7	114.2 (5)
O2—Nd1—O4^i	87.86 (11)	C20—C15—O7	124.7 (5)
O4^i—Nd1—O1	78.25 (10)	C15—C16—C17	119.3 (6)
O2—Nd1—O5^i	75.61 (10)	C15—C16—H16	120.3
O4^i—Nd1—O5^i	74.40 (10)	C17—C16—H16	120.3
O1—Nd1—O5^i	128.26 (10)	C18—C17—C16	120.2 (7)
O2—Nd1—O6^ii	77.15 (10)	C18—C17—H17	119.9
O4^i—Nd1—O6^ii	78.23 (11)	C16—C17—H17	119.9
O1—Nd1—O6^ii	69.68 (10)	C19—C18—C17	121.1 (7)
O5^i—Nd1—O6^ii	141.73 (10)	C19—C18—H18	119.4
O4^i—Nd1—O3	120.72 (11)	C17—C18—H18	119.4
O5^i—Nd1—O3	84.18 (10)	C18—C19—C20	119.8 (7)
O6^ii—Nd1—O3	133.35 (10)	C18—C19—H19	120.1
O4^i—Nd1—N2	148.77 (11)	C20—C19—H19	120.1
O5^i—Nd1—N2	136.69 (11)	C15—C20—C19	118.4 (6)
O6^ii—Nd1—N2	72.83 (12)	C15—C20—H20	120.8
O4^i—Nd1—N1	150.26 (11)	C19—C20—H20	120.8
O5^i—Nd1—N1	77.04 (11)	O6—C21—O2	127.2 (4)
O6^ii—Nd1—N1	121.92 (12)	O6—C21—C22	119.7 (4)
O4^i—Nd1—O4	72.85 (11)	O2—C21—C22	112.9 (4)
O5^i—Nd1—O4	65.13 (10)	O8—C22—C21	111.2 (4)
O6^ii—Nd1—O4	130.06 (10)	O8—C22—H22A	109.4
C13—O1—Nd1	129.9 (3)	C21—C22—H22A	109.4
C21—O2—Nd1	151.3 (3)	O8—C22—H22B	109.4
C29—O3—Nd1	101.2 (3)	C21—C22—H22B	109.4
C29—O4—Nd1^i	163.0 (3)	H22A—C22—H22B	108.0
C29—O4—Nd1	87.8 (3)	C24—C23—O8	124.8 (4)
Nd1^i—O4—Nd1	107.15 (11)	C24—C23—C28	119.8 (5)
C13—O5—Nd1^i	137.8 (3)	O8—C23—C28	115.4 (5)
C21—O6—Nd1^ii	149.9 (3)	C23—C24—C25	119.8 (6)
C15—O7—C14	116.8 (4)	C23—C24—H24	120.1
C23—O8—C22	117.6 (4)	C25—C24—H24	120.1
C31—O9—C30	116.8 (6)	C24—C25—C26	120.9 (6)
C1—N1—C5	118.7 (4)	C24—C25—H25	119.6
C1—N1—Nd1	120.1 (3)	C26—C25—H25	119.6
C5—N1—Nd1	119.7 (3)	C27—C26—C25	119.5 (6)
C12—N2—C9	118.5 (4)	C27—C26—H26	120.3
C12—N2—Nd1	119.7 (3)	C25—C26—H26	120.3
C9—N2—Nd1	121.5 (3)	C26—C27—C28	120.6 (6)
N1—C1—C2	123.2 (5)	C26—C27—H27	119.7
N1—C1—H1	118.4	C28—C27—H27	119.7
C2—C1—H1	118.4	C27—C28—C23	119.5 (6)
C3—C2—C1	117.6 (6)	C27—C28—H28	120.2
C3—C2—H2	121.2	C23—C28—H28	120.2
C1—C2—H2	121.2	O3—C29—O4	122.7 (4)
C4—C3—C2	121.5 (6)	O3—C29—C30	120.6 (4)
C4—C3—H3	119.2	O4—C29—C30	116.8 (4)
C2—C3—H3	119.2	O9—C30—C29	113.9 (4)
C3—C4—C5	117.6 (6)	O9—C30—H30A	108.8
C3—C4—C6	124.2 (7)	C29—C30—H30A	108.8
C5—C4—C6	118.1 (7)	O9—C30—H30B	108.8
N1—C5—C9	118.7 (4)	C29—C30—H30B	108.8
N1—C5—C4	121.4 (5)	H30A—C30—H30B	107.7
C9—C5—C4	120.0 (5)	O9—C31—C32	125.5 (10)
C7—C6—C4	121.2 (7)	O9—C31—C36	113.3 (10)
C7—C6—H6	119.4	C32—C31—C36	121.2 (10)
C4—C6—H6	119.4	C31—C32—C33	116.6 (10)
C6—C7—C8	122.2 (6)	C31—C32—H32	121.7
C6—C7—H7	118.9	C33—C32—H32	121.7
C8—C7—H7	118.9	C34—C33—C32	121.0 (11)
C10—C8—C7	124.0 (6)	C34—C33—H33	119.5
C10—C8—C9	117.1 (6)	C32—C33—H33	119.5
C7—C8—C9	118.8 (6)	C33—C34—C35	125.7 (10)
N2—C9—C5	118.8 (4)	C33—C34—H34	117.1
N2—C9—C8	121.8 (5)	C35—C34—H34	117.1
C5—C9—C8	119.4 (5)	C34—C35—C36	115.1 (10)
C11—C10—C8	120.7 (5)	C34—C35—H35	122.4
C11—C10—H10	119.6	C36—C35—H35	122.4
C8—C10—H10	119.6	C35—C36—C31	120.1 (11)
C10—C11—C12	119.2 (6)	C35—C36—H36	119.9
C10—C11—H11	120.4	C31—C36—H36	119.9

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C30—H30B···O2^iii	0.97	2.40	3.347 (6)	164
C12—H12···O8^ii	0.93	2.59	3.438 (7)	152
C12—H12···O6^ii	0.93	2.47	3.057 (6)	122
C10—H10···O3^iv	0.93	2.34	3.215 (6)	156
C1—H1···O5^i	0.93	2.44	3.130 (6)	132

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.