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Acta Crystallogr Sect E Struct Rep Online. 2010 February 1; 66(Pt 2): m221–m222.
Published online 2010 January 30. doi:  10.1107/S1600536810003041
PMCID: PMC2979843

Tetra-μ-benzoato-κ4 O:O′;κ3 O:O,O′;κ3 O,O′:O′-bis­[(benzoato-κ2 O,O′)(1,10-phenanthroline-κ2 N,N′)neodymium(III)]

Abstract

The complete mol­ecule of the title compound, [Nd2(C7H5O2)6(C12H8N2)2], is generated by a crystallographic inversion center. The two NdIII ions are linked by four bridging benzoate ions, with an Nd(...)Nd separation of 4.0360 (2) Å. As well as the bridging ligands, each NdIII ion is coordinated by one N,N′-bidentate phenanthroline ligand and an O,O′-bidentate benzoate ion. The resulting irregular nine-coordinated geometry of the NdIII ion is completed by seven O and two N atoms. The mol­ecular structure is stabilized by intra­molecular C—H(...)O hydrogen bonds. In the crystal structure, mol­ecules are linked into infinite chains along the c axis by inter­molecular C—H(...)O hydrogen bonds. The crystal structure is consolidated by weak inter­molecular C—H(...)π inter­actions.

Related literature

For general background to and applications of NdIII complexes, see: Swavey & Swavey (2009 [triangle]). For related Ln–benzoato complexes, see: Niu et al. (1999 [triangle]); Niu et al. (2002 [triangle]); Shi et al. (2001 [triangle]). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m221-scheme1.jpg

Experimental

Crystal data

  • [Nd2(C7H5O2)6(C12H8N2)2]
  • M r = 1375.55
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m221-efi1.jpg
  • a = 10.7954 (3) Å
  • b = 11.8702 (4) Å
  • c = 12.2660 (7) Å
  • α = 104.925 (1)°
  • β = 93.831 (1)°
  • γ = 112.877 (1)°
  • V = 1374.49 (10) Å3
  • Z = 1
  • Mo Kα radiation
  • μ = 1.94 mm−1
  • T = 100 K
  • 0.69 × 0.41 × 0.13 mm

Data collection

  • Bruker SMART APEX DUO CCD diffractometer
  • Absorption correction: multi-scan SADABS (Bruker, 2009 [triangle]) T min = 0.347, T max = 0.784
  • 46897 measured reflections
  • 11933 independent reflections
  • 11529 reflections with I > 2σ(I)
  • R int = 0.020

Refinement

  • R[F 2 > 2σ(F 2)] = 0.016
  • wR(F 2) = 0.071
  • S = 1.39
  • 11933 reflections
  • 379 parameters
  • H-atom parameters constrained
  • Δρmax = 1.26 e Å−3
  • Δρmin = −1.51 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 [triangle]).

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810003041/hb5308sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810003041/hb5308Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

SGT and PHO thank Universiti Sains Malaysia (USM) for the University Grant (No. 1001/229/PKIMIA/815002) for this research. HKF and JHG thank USM for the Research University Golden Goose grant (No. 1001/PFIZIK/811012). JHG also thanks USM for the award of a USM fellowship.

supplementary crystallographic information

Comment

Lanthanide complexes with organic ligands, especially NdIII complexes, are often used in magnetic resonance imaging (MRI) because NdIII complexes emit in the near infrared region (NIR) (Swavey & Swavey, 2009). The crystal structure obtained from this complex are slightly different from the other Ln-benzoato complexes, such as LaIII (Shi et al., 2001), SmIII (Niu et al., 1999), and GdIII (Niu et al., 2002) due to the lanthanide contraction.

The asymmetric unit of the title complex (Fig. 1) lies on a crystallographic inversion center and comprises of one-half molecule [symmetry code of atoms labelled with suffix A: -x, -y+1, -z+1]. The two NdIII ions are linked by four benzoate ions, with an Nd—Nd distance of 4.0360 (2) Å. Among the four benzoate ions, two of them also behave as chelating ligands to the NdIII ions. Each NdIII ion is coordinated by one phenanthroline heterocycle and a bidentate benzoate ion. The irregular nine-coordinated geometry of the NdIII ion is completed by seven benzoate O atoms and two phenanthroline N atoms. Intramolecular C11—H11A···O6 and C26—H26A···O2 hydrogen bonds (Table 2) stabilize the molecular structure. Bond lengths of Nd—O and Nd—N are listed in Table 1. All other bond lengths and angles are comparable to a closely La-benzoato complex (Shi et al., 2001).

In the crystal structure, intermolecular C3—H3A···O1 hydrogen bonds (Table 2) link the molecules into infinite chains along the c axis (Fig. 2). The crystal structure is further stabilized by weak intermolecular C7A—H7A···Cg1, C16—H16A···Cg2, C17—H17A···Cg3, C24—H24A···Cg4 and C30—H30A···Cg5 interactions (Table 2).

Experimental

NdCl3.6H2O was prepared by dissolving neodymium oxide in hydrochloric acid and then dried. Metal salt (0.5 mmol) in methanol was added into a solution (methanol-H2O, 1:1) of 1,10-phenanthroline (0.5 mmol) and benzoic acid (1.5 mmol). The mixture was refluxed for 24 h to give a pink solution. The solution was filtered at room temperature and purple plates of (I) were obtained after 10 days.

Refinement

All aromatic hydrogen atoms were placed in their calculated positions, with C—H = 0.93 Å, and refined using a riding model with Uiso = 1.2 Ueq(C). The highest residual electron density peak is located at 1.25 Å from O4 and the deepest hole is located at 1.51 Å from Nd1.

Figures

Fig. 1.
The molecular structure of (I) showing 20% probability displacement ellipsoids for non-H atoms. The suffix A corresponds to the symmetry code [-x, -y+1, -z+1].
Fig. 2.
The crystal structure of (I), viewed along the a axis, showing one-dimensional infinite chains along the c axis. Intermolecular hydrogen bonds are shown as dashed lines.

Crystal data

[Nd2(C7H5O2)6(C12H8N2)2]Z = 1
Mr = 1375.55F(000) = 686
Triclinic, P1Dx = 1.662 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.7954 (3) ÅCell parameters from 9761 reflections
b = 11.8702 (4) Åθ = 3.0–37.6°
c = 12.2660 (7) ŵ = 1.94 mm1
α = 104.925 (1)°T = 100 K
β = 93.831 (1)°Plate, purple
γ = 112.877 (1)°0.69 × 0.41 × 0.13 mm
V = 1374.49 (10) Å3

Data collection

Bruker SMART APEX DUO CCD diffractometer11933 independent reflections
Radiation source: fine-focus sealed tube11529 reflections with I > 2σ(I)
graphiteRint = 0.020
[var phi] and ω scansθmax = 35.0°, θmin = 2.7°
Absorption correction: multi-scan SADABS (Bruker, 2009)h = −17→17
Tmin = 0.347, Tmax = 0.784k = −18→19
46897 measured reflectionsl = −19→19

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.016Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.071H-atom parameters constrained
S = 1.39w = 1/[σ2(Fo2) + (0.039P)2 + 0.2397P] where P = (Fo2 + 2Fc2)/3
11933 reflections(Δ/σ)max < 0.001
379 parametersΔρmax = 1.25 e Å3
0 restraintsΔρmin = −1.51 e Å3

Special details

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1)K.
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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)

xyzUiso*/Ueq
Nd10.135991 (5)0.561522 (5)0.646953 (5)0.01014 (3)
O10.07381 (10)0.68363 (9)0.82160 (9)0.01641 (16)
O20.27604 (10)0.77974 (10)0.77735 (9)0.01605 (16)
O30.15987 (11)0.35844 (10)0.56526 (9)0.01848 (18)
O40.00549 (10)0.36146 (9)0.44049 (9)0.01530 (16)
O50.08829 (10)0.59147 (10)0.34526 (9)0.01613 (16)
O60.24489 (10)0.63755 (10)0.49909 (9)0.01578 (16)
N10.19179 (12)0.48650 (11)0.82052 (10)0.01452 (17)
N20.38701 (11)0.57086 (11)0.69470 (10)0.01398 (17)
C10.30009 (13)0.45576 (12)0.82829 (11)0.01378 (19)
C20.10022 (15)0.45161 (13)0.88670 (12)0.0171 (2)
H2A0.02660.47350.88220.021*
C30.10869 (16)0.38359 (14)0.96296 (12)0.0192 (2)
H3A0.04400.36361.00960.023*
C40.21506 (16)0.34718 (14)0.96717 (12)0.0195 (2)
H4A0.22110.29921.01480.023*
C50.31456 (14)0.38298 (13)0.89895 (12)0.0166 (2)
C60.42959 (16)0.35029 (14)0.90061 (13)0.0202 (2)
H6A0.43710.29930.94460.024*
C70.52686 (16)0.39300 (15)0.83879 (13)0.0203 (2)
H7A0.60070.37120.84120.024*
C80.51832 (13)0.47134 (13)0.76955 (12)0.0163 (2)
C90.61982 (14)0.52029 (14)0.70660 (13)0.0191 (2)
H9A0.69820.50550.71140.023*
C100.60218 (14)0.59012 (14)0.63790 (13)0.0192 (2)
H10A0.66730.62180.59460.023*
C110.48338 (14)0.61251 (13)0.63463 (12)0.0169 (2)
H11A0.47180.65920.58760.020*
C120.40383 (13)0.50067 (12)0.76196 (11)0.01365 (19)
C130.18596 (13)0.78037 (12)0.83975 (11)0.01332 (19)
C140.21680 (13)0.89994 (12)0.93665 (10)0.01395 (19)
C150.11566 (16)0.91061 (14)0.99806 (12)0.0187 (2)
H15A0.02760.84490.97680.022*
C160.14606 (19)1.01942 (16)1.09120 (13)0.0238 (3)
H16A0.07831.02681.13170.029*
C170.2775 (2)1.11663 (16)1.12335 (13)0.0259 (3)
H17A0.29831.18831.18660.031*
C180.37869 (17)1.10783 (14)1.06176 (13)0.0231 (3)
H18A0.46671.17361.08320.028*
C190.34719 (15)0.99948 (13)0.96739 (12)0.0176 (2)
H19A0.41400.99400.92490.021*
C200.06862 (12)0.30308 (12)0.47633 (11)0.01305 (18)
C210.03417 (13)0.16578 (11)0.41377 (11)0.01327 (18)
C220.12719 (14)0.11477 (13)0.43391 (12)0.0163 (2)
H22A0.21120.16740.48260.020*
C230.09434 (16)−0.01436 (14)0.38135 (13)0.0196 (2)
H23A0.1570−0.04780.39390.023*
C24−0.03202 (17)−0.09346 (14)0.31012 (13)0.0214 (2)
H24A−0.0544−0.18020.27580.026*
C25−0.12551 (16)−0.04316 (13)0.28996 (13)0.0208 (2)
H25A−0.2102−0.09630.24240.025*
C26−0.09184 (14)0.08677 (13)0.34117 (12)0.0163 (2)
H26A−0.15350.12070.32690.020*
C270.20609 (13)0.65426 (12)0.40696 (11)0.01327 (19)
C280.30895 (12)0.75547 (12)0.36677 (11)0.01323 (18)
C290.26872 (14)0.78761 (13)0.27284 (12)0.0171 (2)
H29A0.17820.74530.23420.020*
C300.36372 (16)0.88293 (15)0.23681 (14)0.0211 (2)
H30A0.33620.90500.17500.025*
C310.49950 (16)0.94497 (14)0.29314 (14)0.0218 (2)
H31A0.56281.00870.26920.026*
C320.54037 (15)0.91166 (15)0.38495 (14)0.0230 (3)
H32A0.63160.95190.42170.028*
C330.44521 (14)0.81793 (14)0.42247 (12)0.0192 (2)
H33A0.47290.79700.48500.023*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Nd10.01005 (3)0.00866 (3)0.01053 (3)0.00329 (2)0.00192 (2)0.00210 (2)
O10.0166 (4)0.0123 (4)0.0174 (4)0.0039 (3)0.0051 (3)0.0028 (3)
O20.0153 (4)0.0136 (4)0.0154 (4)0.0041 (3)0.0038 (3)0.0012 (3)
O30.0172 (4)0.0130 (4)0.0209 (4)0.0069 (3)−0.0032 (3)−0.0010 (3)
O40.0173 (4)0.0138 (4)0.0179 (4)0.0090 (3)0.0041 (3)0.0057 (3)
O50.0132 (4)0.0154 (4)0.0163 (4)0.0025 (3)0.0025 (3)0.0049 (3)
O60.0148 (4)0.0176 (4)0.0156 (4)0.0058 (3)0.0044 (3)0.0074 (3)
N10.0149 (4)0.0144 (4)0.0145 (4)0.0065 (3)0.0031 (3)0.0042 (3)
N20.0132 (4)0.0125 (4)0.0138 (4)0.0044 (3)0.0016 (3)0.0021 (3)
C10.0148 (5)0.0123 (4)0.0127 (4)0.0058 (4)0.0007 (4)0.0017 (4)
C20.0194 (5)0.0165 (5)0.0168 (5)0.0079 (4)0.0058 (4)0.0060 (4)
C30.0229 (6)0.0189 (6)0.0176 (5)0.0087 (5)0.0066 (5)0.0078 (4)
C40.0241 (6)0.0177 (5)0.0174 (5)0.0084 (5)0.0032 (4)0.0072 (4)
C50.0185 (5)0.0147 (5)0.0157 (5)0.0073 (4)0.0000 (4)0.0037 (4)
C60.0236 (6)0.0174 (5)0.0209 (6)0.0109 (5)−0.0003 (5)0.0054 (4)
C70.0210 (6)0.0189 (6)0.0219 (6)0.0125 (5)−0.0003 (5)0.0023 (5)
C80.0154 (5)0.0145 (5)0.0172 (5)0.0078 (4)0.0007 (4)0.0004 (4)
C90.0161 (5)0.0173 (5)0.0221 (6)0.0087 (4)0.0036 (4)0.0005 (4)
C100.0153 (5)0.0185 (5)0.0215 (6)0.0067 (4)0.0057 (4)0.0023 (4)
C110.0146 (5)0.0162 (5)0.0178 (5)0.0050 (4)0.0037 (4)0.0040 (4)
C120.0131 (4)0.0120 (4)0.0135 (5)0.0053 (4)0.0005 (4)0.0005 (4)
C130.0151 (5)0.0119 (4)0.0124 (4)0.0057 (4)0.0020 (4)0.0031 (4)
C140.0177 (5)0.0122 (4)0.0114 (4)0.0067 (4)0.0013 (4)0.0026 (4)
C150.0237 (6)0.0174 (5)0.0171 (5)0.0105 (5)0.0060 (4)0.0051 (4)
C160.0362 (8)0.0233 (6)0.0171 (6)0.0191 (6)0.0069 (5)0.0037 (5)
C170.0409 (9)0.0196 (6)0.0164 (6)0.0175 (6)−0.0023 (5)−0.0014 (5)
C180.0286 (7)0.0146 (5)0.0190 (6)0.0065 (5)−0.0049 (5)0.0002 (4)
C190.0204 (5)0.0142 (5)0.0150 (5)0.0058 (4)−0.0009 (4)0.0025 (4)
C200.0128 (4)0.0101 (4)0.0160 (5)0.0053 (4)0.0034 (4)0.0027 (4)
C210.0143 (5)0.0105 (4)0.0146 (5)0.0056 (4)0.0024 (4)0.0026 (4)
C220.0175 (5)0.0141 (5)0.0179 (5)0.0087 (4)0.0025 (4)0.0030 (4)
C230.0259 (6)0.0153 (5)0.0200 (6)0.0125 (5)0.0047 (5)0.0033 (4)
C240.0308 (7)0.0131 (5)0.0185 (5)0.0099 (5)0.0026 (5)0.0011 (4)
C250.0235 (6)0.0131 (5)0.0192 (6)0.0045 (4)−0.0017 (5)0.0008 (4)
C260.0173 (5)0.0126 (5)0.0165 (5)0.0051 (4)−0.0003 (4)0.0033 (4)
C270.0137 (5)0.0115 (4)0.0145 (5)0.0050 (4)0.0047 (4)0.0037 (4)
C280.0132 (4)0.0116 (4)0.0148 (5)0.0045 (4)0.0048 (4)0.0044 (4)
C290.0158 (5)0.0173 (5)0.0211 (5)0.0076 (4)0.0048 (4)0.0096 (4)
C300.0224 (6)0.0202 (6)0.0251 (6)0.0089 (5)0.0073 (5)0.0136 (5)
C310.0216 (6)0.0178 (6)0.0246 (6)0.0039 (5)0.0084 (5)0.0104 (5)
C320.0170 (5)0.0219 (6)0.0228 (6)−0.0005 (5)0.0024 (5)0.0093 (5)
C330.0153 (5)0.0191 (5)0.0189 (5)0.0016 (4)0.0020 (4)0.0082 (4)

Geometric parameters (Å, °)

Nd1—O4i2.3856 (10)C10—H10A0.9300
Nd1—O62.4060 (10)C11—H11A0.9300
Nd1—O5i2.4230 (10)C13—C141.4996 (18)
Nd1—O22.4600 (10)C14—C191.3879 (19)
Nd1—O32.4810 (10)C14—C151.3942 (19)
Nd1—O12.5475 (10)C15—C161.393 (2)
Nd1—N12.6288 (12)C15—H15A0.9300
Nd1—N22.6870 (11)C16—C171.385 (3)
Nd1—O42.8039 (10)C16—H16A0.9300
O1—C131.2591 (16)C17—C181.390 (3)
O2—C131.2781 (16)C17—H17A0.9300
O3—C201.2553 (16)C18—C191.396 (2)
O4—C201.2736 (15)C18—H18A0.9300
O4—Nd1i2.3855 (10)C19—H19A0.9300
O5—C271.2607 (16)C20—C211.4932 (17)
O5—Nd1i2.4230 (10)C21—C261.3925 (18)
O6—C271.2684 (16)C21—C221.3974 (18)
N1—C21.3304 (17)C22—C231.3887 (19)
N1—C11.3579 (17)C22—H22A0.9300
N2—C111.3266 (17)C23—C241.389 (2)
N2—C121.3636 (17)C23—H23A0.9300
C1—C51.4122 (19)C24—C251.395 (2)
C1—C121.4427 (18)C24—H24A0.9300
C2—C31.404 (2)C25—C261.3929 (19)
C2—H2A0.9300C25—H25A0.9300
C3—C41.378 (2)C26—H26A0.9300
C3—H3A0.9300C27—C281.5034 (17)
C4—C51.408 (2)C28—C331.3918 (19)
C4—H4A0.9300C28—C291.3965 (19)
C5—C61.438 (2)C29—C301.3939 (19)
C6—C71.351 (2)C29—H29A0.9300
C6—H6A0.9300C30—C311.390 (2)
C7—C81.435 (2)C30—H30A0.9300
C7—H7A0.9300C31—C321.385 (2)
C8—C91.408 (2)C31—H31A0.9300
C8—C121.4118 (18)C32—C331.394 (2)
C9—C101.376 (2)C32—H32A0.9300
C9—H9A0.9300C33—H33A0.9300
C10—C111.407 (2)
O4i—Nd1—O673.10 (3)C9—C10—H10A120.7
O4i—Nd1—O5i79.74 (3)C11—C10—H10A120.7
O6—Nd1—O5i135.40 (3)N2—C11—C10123.81 (13)
O4i—Nd1—O290.44 (4)N2—C11—H11A118.1
O6—Nd1—O286.17 (3)C10—C11—H11A118.1
O5i—Nd1—O2129.27 (3)N2—C12—C8122.72 (12)
O4i—Nd1—O3126.97 (3)N2—C12—C1118.10 (11)
O6—Nd1—O388.34 (4)C8—C12—C1119.17 (12)
O5i—Nd1—O380.45 (4)O1—C13—O2121.55 (12)
O2—Nd1—O3138.41 (3)O1—C13—C14120.10 (11)
O4i—Nd1—O178.44 (3)O2—C13—C14118.35 (11)
O6—Nd1—O1129.08 (3)O1—C13—Nd162.75 (7)
O5i—Nd1—O176.84 (3)O2—C13—Nd158.84 (7)
O2—Nd1—O152.45 (3)C14—C13—Nd1176.57 (9)
O3—Nd1—O1141.78 (4)C19—C14—C15119.60 (12)
O4i—Nd1—N1146.80 (3)C19—C14—C13120.12 (12)
O6—Nd1—N1138.90 (3)C15—C14—C13120.26 (12)
O5i—Nd1—N178.15 (3)C16—C15—C14120.19 (14)
O2—Nd1—N184.74 (4)C16—C15—H15A119.9
O3—Nd1—N172.90 (4)C14—C15—H15A119.9
O1—Nd1—N172.63 (3)C17—C16—C15119.79 (15)
O4i—Nd1—N2147.67 (3)C17—C16—H16A120.1
O6—Nd1—N277.31 (3)C15—C16—H16A120.1
O5i—Nd1—N2131.81 (3)C16—C17—C18120.50 (14)
O2—Nd1—N274.72 (3)C16—C17—H17A119.8
O3—Nd1—N263.86 (3)C18—C17—H17A119.8
O1—Nd1—N2111.81 (3)C17—C18—C19119.49 (15)
N1—Nd1—N261.62 (3)C17—C18—H18A120.3
O4i—Nd1—O478.19 (3)C19—C18—H18A120.3
O6—Nd1—O473.81 (3)C14—C19—C18120.38 (14)
O5i—Nd1—O466.35 (3)C14—C19—H19A119.8
O2—Nd1—O4159.09 (3)C18—C19—H19A119.8
O3—Nd1—O448.81 (3)O3—C20—O4121.21 (12)
O1—Nd1—O4139.16 (3)O3—C20—C21118.34 (11)
N1—Nd1—O4114.30 (3)O4—C20—C21120.45 (11)
N2—Nd1—O4105.85 (3)O3—C20—Nd153.53 (6)
C13—O1—Nd191.18 (8)O4—C20—Nd168.32 (7)
C13—O2—Nd194.76 (8)C21—C20—Nd1167.86 (9)
C20—O3—Nd1102.46 (8)C26—C21—C22119.87 (12)
C20—O4—Nd1i171.01 (9)C26—C21—C20120.95 (11)
C20—O4—Nd186.72 (7)C22—C21—C20119.08 (11)
Nd1i—O4—Nd1101.81 (3)C23—C22—C21120.12 (13)
C27—O5—Nd1i139.15 (9)C23—C22—H22A119.9
C27—O6—Nd1135.75 (8)C21—C22—H22A119.9
C2—N1—C1118.06 (12)C24—C23—C22119.98 (13)
C2—N1—Nd1120.55 (9)C24—C23—H23A120.0
C1—N1—Nd1119.81 (8)C22—C23—H23A120.0
C11—N2—C12117.69 (12)C23—C24—C25120.16 (13)
C11—N2—Nd1122.51 (9)C23—C24—H24A119.9
C12—N2—Nd1117.62 (8)C25—C24—H24A119.9
N1—C1—C5122.46 (12)C26—C25—C24119.92 (13)
N1—C1—C12118.03 (11)C26—C25—H25A120.0
C5—C1—C12119.51 (12)C24—C25—H25A120.0
N1—C2—C3123.59 (13)C25—C26—C21119.94 (13)
N1—C2—H2A118.2C25—C26—H26A120.0
C3—C2—H2A118.2C21—C26—H26A120.0
C4—C3—C2118.44 (13)O5—C27—O6125.19 (12)
C4—C3—H3A120.8O5—C27—C28117.15 (11)
C2—C3—H3A120.8O6—C27—C28117.66 (11)
C3—C4—C5119.63 (13)C33—C28—C29119.27 (12)
C3—C4—H4A120.2C33—C28—C27120.46 (12)
C5—C4—H4A120.2C29—C28—C27120.27 (11)
C4—C5—C1117.69 (12)C30—C29—C28120.22 (13)
C4—C5—C6122.59 (13)C30—C29—H29A119.9
C1—C5—C6119.70 (13)C28—C29—H29A119.9
C7—C6—C5120.58 (13)C31—C30—C29120.09 (13)
C7—C6—H6A119.7C31—C30—H30A120.0
C5—C6—H6A119.7C29—C30—H30A120.0
C6—C7—C8121.22 (13)C32—C31—C30119.87 (13)
C6—C7—H7A119.4C32—C31—H31A120.1
C8—C7—H7A119.4C30—C31—H31A120.1
C9—C8—C12117.66 (13)C31—C32—C33120.20 (14)
C9—C8—C7122.62 (13)C31—C32—H32A119.9
C12—C8—C7119.71 (13)C33—C32—H32A119.9
C10—C9—C8119.56 (13)C28—C33—C32120.33 (13)
C10—C9—H9A120.2C28—C33—H33A119.8
C8—C9—H9A120.2C32—C33—H33A119.8
C9—C10—C11118.52 (13)
O4i—Nd1—O1—C13−98.30 (8)O1—Nd1—N2—C1272.08 (9)
O6—Nd1—O1—C13−41.56 (9)N1—Nd1—N2—C1217.66 (8)
O5i—Nd1—O1—C13179.68 (8)O4—Nd1—N2—C12−91.79 (9)
O2—Nd1—O1—C131.33 (7)C13—Nd1—N2—C1291.68 (9)
O3—Nd1—O1—C13124.60 (8)C20—Nd1—N2—C12−77.39 (9)
N1—Nd1—O1—C1398.18 (8)Nd1i—Nd1—N2—C12−117.61 (8)
N2—Nd1—O1—C1349.60 (8)C2—N1—C1—C53.41 (19)
O4—Nd1—O1—C13−154.52 (7)Nd1—N1—C1—C5−162.33 (10)
C20—Nd1—O1—C13165.30 (8)C2—N1—C1—C12−176.14 (12)
Nd1i—Nd1—O1—C13−122.72 (7)Nd1—N1—C1—C1218.12 (15)
O4i—Nd1—O2—C1373.69 (8)C1—N1—C2—C3−0.8 (2)
O6—Nd1—O2—C13146.72 (8)Nd1—N1—C2—C3164.86 (11)
O5i—Nd1—O2—C13−3.38 (10)N1—C2—C3—C4−2.1 (2)
O3—Nd1—O2—C13−130.13 (8)C2—C3—C4—C52.4 (2)
O1—Nd1—O2—C13−1.31 (7)C3—C4—C5—C10.0 (2)
N1—Nd1—O2—C13−73.41 (8)C3—C4—C5—C6178.85 (14)
N2—Nd1—O2—C13−135.39 (8)N1—C1—C5—C4−3.0 (2)
O4—Nd1—O2—C13130.12 (9)C12—C1—C5—C4176.50 (12)
C20—Nd1—O2—C13−155.92 (10)N1—C1—C5—C6178.08 (12)
Nd1i—Nd1—O2—C1389.53 (8)C12—C1—C5—C6−2.39 (19)
O4i—Nd1—O3—C20−7.61 (10)C4—C5—C6—C7−176.12 (14)
O6—Nd1—O3—C20−74.92 (9)C1—C5—C6—C72.7 (2)
O5i—Nd1—O3—C2061.73 (9)C5—C6—C7—C8−0.3 (2)
O2—Nd1—O3—C20−157.25 (8)C6—C7—C8—C9178.22 (14)
O1—Nd1—O3—C20115.79 (9)C6—C7—C8—C12−2.5 (2)
N1—Nd1—O3—C20142.18 (9)C12—C8—C9—C10−2.2 (2)
N2—Nd1—O3—C20−151.59 (10)C7—C8—C9—C10177.14 (14)
O4—Nd1—O3—C20−5.11 (7)C8—C9—C10—C111.2 (2)
C13—Nd1—O3—C20160.95 (8)C12—N2—C11—C10−1.04 (19)
Nd1i—Nd1—O3—C20−6.30 (8)Nd1—N2—C11—C10−163.83 (10)
O4i—Nd1—O4—C20−177.11 (9)C9—C10—C11—N20.5 (2)
O6—Nd1—O4—C20107.28 (8)C11—N2—C12—C8−0.05 (18)
O5i—Nd1—O4—C20−93.26 (8)Nd1—N2—C12—C8163.59 (9)
O2—Nd1—O4—C20124.56 (10)C11—N2—C12—C1179.54 (11)
O3—Nd1—O4—C204.93 (7)Nd1—N2—C12—C1−16.82 (14)
O1—Nd1—O4—C20−120.82 (8)C9—C8—C12—N21.64 (19)
N1—Nd1—O4—C20−29.59 (8)C7—C8—C12—N2−177.71 (12)
N2—Nd1—O4—C2035.95 (8)C9—C8—C12—C1−177.94 (12)
C13—Nd1—O4—C20−154.15 (10)C7—C8—C12—C12.71 (18)
Nd1i—Nd1—O4—C20−177.11 (9)N1—C1—C12—N2−0.35 (17)
O4i—Nd1—O4—Nd1i0.0C5—C1—C12—N2−179.91 (12)
O6—Nd1—O4—Nd1i−75.61 (4)N1—C1—C12—C8179.25 (11)
O5i—Nd1—O4—Nd1i83.85 (4)C5—C1—C12—C8−0.30 (18)
O2—Nd1—O4—Nd1i−58.33 (10)Nd1—O1—C13—O2−2.37 (13)
O3—Nd1—O4—Nd1i−177.96 (6)Nd1—O1—C13—C14177.83 (10)
O1—Nd1—O4—Nd1i56.29 (6)Nd1—O2—C13—O12.47 (14)
N1—Nd1—O4—Nd1i147.52 (3)Nd1—O2—C13—C14−177.74 (10)
N2—Nd1—O4—Nd1i−146.94 (3)O1—C13—C14—C19170.57 (13)
C13—Nd1—O4—Nd1i22.96 (11)O2—C13—C14—C19−9.23 (19)
C20—Nd1—O4—Nd1i177.11 (9)Nd1—C13—C14—C19−43.6 (16)
O4i—Nd1—O6—C27−24.01 (12)O1—C13—C14—C15−7.96 (19)
O5i—Nd1—O6—C2731.03 (14)O2—C13—C14—C15172.24 (12)
O2—Nd1—O6—C27−115.64 (13)Nd1—C13—C14—C15137.8 (15)
O3—Nd1—O6—C27105.61 (12)C19—C14—C15—C16−1.3 (2)
O1—Nd1—O6—C27−82.91 (13)C13—C14—C15—C16177.23 (13)
N1—Nd1—O6—C27166.87 (11)C14—C15—C16—C17−0.6 (2)
N2—Nd1—O6—C27169.17 (13)C15—C16—C17—C181.5 (2)
O4—Nd1—O6—C2758.26 (12)C16—C17—C18—C19−0.5 (2)
C13—Nd1—O6—C27−100.77 (12)C15—C14—C19—C182.3 (2)
C20—Nd1—O6—C2782.26 (12)C13—C14—C19—C18−176.25 (13)
Nd1i—Nd1—O6—C2721.25 (12)C17—C18—C19—C14−1.4 (2)
O4i—Nd1—N1—C218.15 (14)Nd1—O3—C20—O49.94 (14)
O6—Nd1—N1—C2178.90 (9)Nd1—O3—C20—C21−169.30 (9)
O5i—Nd1—N1—C2−31.09 (10)Nd1i—O4—C20—O3−170.2 (5)
O2—Nd1—N1—C2100.88 (10)Nd1—O4—C20—O3−8.59 (12)
O3—Nd1—N1—C2−114.61 (11)Nd1i—O4—C20—C219.0 (6)
O1—Nd1—N1—C248.65 (10)Nd1—O4—C20—C21170.64 (11)
N2—Nd1—N1—C2176.34 (11)Nd1i—O4—C20—Nd1−161.6 (6)
O4—Nd1—N1—C2−88.11 (10)O3—C20—C21—C26157.87 (13)
C13—Nd1—N1—C275.05 (10)O4—C20—C21—C26−21.38 (19)
C20—Nd1—N1—C2−100.15 (10)Nd1—C20—C21—C26112.6 (4)
Nd1i—Nd1—N1—C2−58.31 (12)O3—C20—C21—C22−18.49 (18)
O4i—Nd1—N1—C1−176.47 (8)O4—C20—C21—C22162.26 (12)
O6—Nd1—N1—C1−15.72 (12)Nd1—C20—C21—C22−63.7 (4)
O5i—Nd1—N1—C1134.29 (10)C26—C21—C22—C230.2 (2)
O2—Nd1—N1—C1−93.74 (10)C20—C21—C22—C23176.63 (12)
O3—Nd1—N1—C150.77 (9)C21—C22—C23—C24−1.0 (2)
O1—Nd1—N1—C1−145.97 (10)C22—C23—C24—C250.9 (2)
N2—Nd1—N1—C1−18.27 (9)C23—C24—C25—C260.2 (2)
O4—Nd1—N1—C177.27 (10)C24—C25—C26—C21−1.0 (2)
C13—Nd1—N1—C1−119.57 (10)C22—C21—C26—C250.8 (2)
C20—Nd1—N1—C165.23 (10)C20—C21—C26—C25−175.54 (13)
Nd1i—Nd1—N1—C1107.07 (9)Nd1i—O5—C27—O610.3 (2)
O4i—Nd1—N2—C11−21.91 (13)Nd1i—O5—C27—C28−170.72 (9)
O6—Nd1—N2—C112.17 (10)Nd1—O6—C27—O5−28.0 (2)
O5i—Nd1—N2—C11143.22 (9)Nd1—O6—C27—C28152.96 (9)
O2—Nd1—N2—C11−87.28 (10)O5—C27—C28—C33−172.26 (13)
O3—Nd1—N2—C1196.61 (11)O6—C27—C28—C336.83 (18)
O1—Nd1—N2—C11−125.12 (10)O5—C27—C28—C297.60 (18)
N1—Nd1—N2—C11−179.55 (11)O6—C27—C28—C29−173.31 (12)
O4—Nd1—N2—C1171.01 (10)C33—C28—C29—C30−1.2 (2)
C13—Nd1—N2—C11−105.52 (10)C27—C28—C29—C30178.96 (13)
C20—Nd1—N2—C1185.41 (10)C28—C29—C30—C311.0 (2)
Nd1i—Nd1—N2—C1145.18 (11)C29—C30—C31—C320.2 (2)
O4i—Nd1—N2—C12175.30 (8)C30—C31—C32—C33−1.3 (3)
O6—Nd1—N2—C12−160.63 (9)C29—C28—C33—C320.1 (2)
O5i—Nd1—N2—C12−19.57 (11)C27—C28—C33—C32179.95 (14)
O2—Nd1—N2—C12109.92 (9)C31—C32—C33—C281.1 (2)
O3—Nd1—N2—C12−66.19 (9)

Symmetry codes: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg5 are the centroids of the C28–C33, C21–C26 and C14–C19 phenyl rings, respectively. Cg3 and Cg4 are the centroids of the N2/C8–C12 and N1/C1–C15 pyridine rings, respectively.
D—H···AD—HH···AD···AD—H···A
C3—H3A···O1ii0.932.573.4729 (19)163
C11—H11A···O60.932.503.1239 (19)125
C26—H26A···O2i0.932.563.4393 (19)158
C7—H7A···Cg1iii0.932.893.4554 (18)121
C16—H16A···Cg2iv0.932.983.7544 (18)141
C17—H17A···Cg3v0.932.943.7287 (19)143
C24—H24A···Cg4vi0.932.813.6620 (17)153
C30—H30A···Cg5vii0.932.733.6435 (18)167

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5308).

References

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