metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

Bis{μ-1,3-bis­­[2-(5-bromo-2-oxido­benzyl­­idene­amino)ethyl]-2-(5-bromo-2-oxido­phenyl)-1,3-imidazolidine}dineo­dymium(III) N,N-di­methyl­formamide hexa­solvate

aDepartment of Chemistry and Science of Life, Quanzhou Normal University, Fujian 362000, People's Republic of China
*Correspondence e-mail: hml301@163.com

(Received 31 October 2009; accepted 10 November 2009; online 21 November 2009)

In the title centrosymmetric dinuclear complex, [Nd2(C27H24Br3N4O3)2]·6C3H7NO, the NdIII ion is coordinated in a slightly distorted square-anti­prismatic geometry by four N atoms and four O atoms from two centrosymmetrically-related 1,3-bis­[2-(5-bromo-2-oxidobenzyl­amino)eth­yl]-2-(5-bromo-2-oxidophen­yl)-1,3-imidazolidine ligands. The Nd⋯Nd separation is 4.5012 (12) Å.

Related literature

For general background to tripodal ligands, see: Bian et al. (2008[Bian, Z. Y., Sumi, K., Furue, M., Sato, S., Koike, K. & Ishitani, O. (2008). Inorg. Chem. 47, 10801-10803.]); Palaniandavar et al. (2006[Palaniandavar, M., Velusamy, M. & Mayilmurugan, R. (2006). J. Chem. Sci. 118, 601-610.]); Velusamy et al. (2004[Velusamy, M., Mayilmurugan, R. & Palaniandavar, M. (2004). Inorg. Chem. 43, 6284-6293.]). For related structures, see: Fondo et al. (2005[Fondo, M., Deibe, A. M. G., Ocampo, N., Bermejo, M. R. & Sanmartín, J. (2005). Z. Anorg. Allg. Chem. 631, 2041-2045.]); Xie et al. (2009[Xie, Q.-F., Huang, M.-L. & Chen, Y.-M. (2009). Chin. J. Inorg. Chem. 25, 1539-1544.]); Yang et al. (1995[Yang, L.-W., Liu, S., Wong, E., Rettig, S. J. & Orvig, C. (1995). Inorg. Chem. 34, 2164-2178.]).

[Scheme 1]

Experimental

Crystal data
  • [Nd2(C27H24Br3N4O3)2]·6C3H7NO

  • Mr = 2111.46

  • Monoclinic, P 21 /c

  • a = 14.624 (6) Å

  • b = 22.460 (4) Å

  • c = 13.663 (4) Å

  • β = 101.133 (6)°

  • V = 4403 (2) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 3.95 mm−1

  • T = 296 K

  • 0.25 × 0.23 × 0.22 mm

Data collection
  • Bruke APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.438, Tmax = 0.477

  • 25933 measured reflections

  • 8078 independent reflections

  • 5119 reflections with I > 2σ(I)

  • Rint = 0.057

Refinement
  • R[F2 > 2σ(F2)] = 0.046

  • wR(F2) = 0.120

  • S = 1.02

  • 8078 reflections

  • 484 parameters

  • 62 restraints

  • H-atom parameters constrained

  • Δρmax = 0.84 e Å−3

  • Δρmin = −0.78 e Å−3

Table 1
Selected bond lengths (Å)

Nd1—O1i 2.341 (4)
Nd1—O2 2.344 (4)
Nd1—O3 2.448 (4)
Nd1—O3i 2.467 (4)
Nd1—N1i 2.616 (5)
Nd1—N2i 2.864 (4)
Nd1—N3 2.896 (5)
Nd1—N4 2.627 (5)
Symmetry code: (i) -x+2, -y+1, -z+2.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

As the rare-earth ions have unique electronic structures and bonding characteristics, the formation of complexes has managed to maintain its unique electromagnetic nature of light. Tripodal ligand has a semi-rigid structure. It can provide a number of service sites to form thermodynamically stable complexes, and its three side chains are free to flip to form a suitable cavity size to include different guest molecules or ions. Furthermore, the researches of tripodal ligands and their complexes are very active at present (Bian et al., 2008; Palaniandavar et al., 2006; Velusamy et al., 2004).

The molecular diagram of the title compound is presented in Fig. 1. The structure is composed of a dimeric [Nd2(brapi)2] molecule [brapi = 2-(2'-hydroxy-5'-bromophenyl)-1,3-bis[3'-aza-4'-(2''-hydroxy- 5''-bromophenyl)-prop-4'-en-1'-yl]-1,3-imidazolidine], with eight-coordinated NdIII ions linked by two bridging O atoms from the phenolic hydroxyl groups, and six N,N-dimethylformamide (DMF) molecules. The coordination geometry around the NdIII ion may be described as distorted square antiprismatic, with one square plane being defined by O2, O3, N3, N4 [the torsion angle is 3.07 (17)°] and the other defined by O1, O3, N2, N1 [the torsion angle is 2.03 (16)°]. The coordination to the metal of the O atoms and N atoms results in the bond lengths of C—O [1.328 (8)–1.364 (7) Å] and C—N [1.301 (7)–1.527 (7) Å] are longer than those in the ligand (Fondo et al., 2005) and in complexes [Ce2(brapi)2].2DMF (Xie et al., 2009) and [La2(brapi)2].2CHCl3 (Yang et al., 1995). The bond lengths of Nd—O (Table 1) are similar to those in the complexes [Ce2(brapi)2].2DMF and [La2(brapi)2].2CHCl3. It can be seen that there is an intermolecular C—H···O hydrogen bond between the DMF molecule and the ligand. The solvent DMF molecules play a role in stablizing the crystal structure.

Related literature top

For general background to tripodal ligands, see: Bian et al. (2008); Palaniandavar et al. (2006); Velusamy et al. (2004). For related structures, see: Fondo et al. (2005); Xie et al. (2009); Yang et al. (1995).

Experimental top

A mixture of H3brapi (1 mmol), Nd(NO3)3.6H2O (1 mmol) and DMF (12 ml) was sealed in a 18 ml Teflon-lined stainless steel reactor and heated in an oven at 353 K for 5 d, and then slowly cooled to room temperature. Orange hexagonal prism crystals of the title complex were collected.

Refinement top

H atoms were placed at calculated positions (C—H = 0.93–0.98 Å) and were allowed to ride on their parent atoms, with Uiso(H) = 1.2(1.5 for methyl)Ueq(C).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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
[Figure 1] Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. [Symmetry codes: (i) -x+2, -y+1, -z+2.]
Bis{µ-1,3-bis[2-(5-bromo-2-oxidobenzylideneamino)ethyl]-2-(5-bromo-2- oxidophenyl)-1,3-imidazolidine}dineodymium(III) N,N-dimethylformamide hexasolvate top
Crystal data top
[Nd2(C27H24Br3N4O3)2]·6C3H7NOF(000) = 2092
Mr = 2111.46Dx = 1.593 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3640 reflections
a = 14.624 (6) Åθ = 2.3–20.3°
b = 22.460 (4) ŵ = 3.95 mm1
c = 13.663 (4) ÅT = 296 K
β = 101.133 (6)°Prism, orange
V = 4403 (2) Å30.25 × 0.23 × 0.22 mm
Z = 2
Data collection top
Bruke APEXII CCD
diffractometer
8078 independent reflections
Radiation source: fine-focus sealed tube5119 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.057
ϕ and ω scansθmax = 25.5°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1713
Tmin = 0.438, Tmax = 0.477k = 2727
25933 measured reflectionsl = 1616
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0539P)2 + 1.2941P]
where P = (Fo2 + 2Fc2)/3
8078 reflections(Δ/σ)max = 0.001
484 parametersΔρmax = 0.84 e Å3
62 restraintsΔρmin = 0.78 e Å3
Crystal data top
[Nd2(C27H24Br3N4O3)2]·6C3H7NOV = 4403 (2) Å3
Mr = 2111.46Z = 2
Monoclinic, P21/cMo Kα radiation
a = 14.624 (6) ŵ = 3.95 mm1
b = 22.460 (4) ÅT = 296 K
c = 13.663 (4) Å0.25 × 0.23 × 0.22 mm
β = 101.133 (6)°
Data collection top
Bruke APEXII CCD
diffractometer
8078 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
5119 reflections with I > 2σ(I)
Tmin = 0.438, Tmax = 0.477Rint = 0.057
25933 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04662 restraints
wR(F2) = 0.120H-atom parameters constrained
S = 1.02Δρmax = 0.84 e Å3
8078 reflectionsΔρmin = 0.78 e Å3
484 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Nd11.09682 (2)0.516119 (15)0.91542 (2)0.04309 (12)
O10.8295 (3)0.57032 (18)1.1258 (3)0.0549 (12)
O21.1124 (3)0.61662 (18)0.8752 (3)0.0551 (11)
O30.9518 (3)0.55074 (16)0.9608 (3)0.0453 (10)
O40.7262 (6)0.4034 (4)0.5864 (6)0.143 (3)
O50.9895 (8)0.6783 (5)0.4013 (8)0.214 (4)
O60.4457 (4)0.4441 (2)0.1416 (4)0.0840 (16)
N10.7226 (4)0.4679 (2)1.0519 (4)0.0458 (13)
N20.8233 (3)0.44465 (19)0.8871 (3)0.0408 (12)
N30.9378 (4)0.4633 (2)0.7851 (3)0.0451 (13)
N41.0965 (4)0.5268 (2)0.7239 (4)0.0512 (14)
N50.6314 (6)0.4532 (5)0.4580 (6)0.111 (3)
N60.9545 (6)0.6979 (3)0.5551 (7)0.109 (2)
N70.4382 (5)0.3491 (3)0.0826 (4)0.0726 (18)
Br10.50063 (7)0.64057 (4)1.32131 (8)0.1009 (3)
Br21.33362 (7)0.75756 (4)0.61348 (6)0.0850 (3)
Br30.65268 (7)0.68123 (4)0.66156 (8)0.1146 (4)
C10.7576 (5)0.5835 (3)1.1687 (5)0.0470 (16)
C20.6724 (5)0.5486 (3)1.1534 (5)0.0490 (16)
C30.5970 (5)0.5677 (3)1.1966 (5)0.0617 (19)
H30.54150.54631.18330.074*
C40.6030 (5)0.6180 (3)1.2590 (5)0.0628 (19)
C50.6870 (6)0.6513 (3)1.2762 (5)0.067 (2)
H50.69250.68451.31760.080*
C60.7615 (5)0.6349 (3)1.2319 (5)0.068 (2)
H60.81540.65791.24370.081*
C70.6587 (5)0.4961 (3)1.0878 (5)0.0477 (16)
H70.59820.48161.07020.057*
C80.6907 (5)0.4201 (3)0.9770 (4)0.0504 (17)
H8A0.62370.41520.96770.060*
H8B0.72010.38260.99960.060*
C90.7180 (4)0.4389 (3)0.8787 (4)0.0477 (16)
H9A0.69430.40970.82770.057*
H9B0.68890.47680.85780.057*
C100.8680 (5)0.3849 (3)0.8719 (5)0.0569 (18)
H10A0.89610.36770.93570.068*
H10B0.82150.35740.83740.068*
C110.9415 (5)0.3967 (3)0.8102 (5)0.0585 (19)
H11A0.92910.37320.74940.070*
H11B1.00270.38610.84750.070*
C120.9465 (5)0.4751 (3)0.6783 (4)0.0545 (18)
H12A0.91730.51290.65720.065*
H12B0.91320.44430.63590.065*
C131.0481 (5)0.4765 (3)0.6639 (5)0.0579 (18)
H13A1.07880.43920.68580.070*
H13B1.05010.48210.59390.070*
C141.1301 (5)0.5694 (3)0.6763 (5)0.0592 (19)
H141.12810.56370.60850.071*
C151.1575 (5)0.6467 (3)0.8157 (5)0.0525 (17)
C161.1705 (5)0.6250 (3)0.7199 (5)0.0533 (17)
C171.2211 (5)0.6604 (3)0.6599 (5)0.0606 (19)
H171.22780.64660.59750.073*
C181.2598 (5)0.7148 (3)0.6938 (5)0.0606 (19)
C191.2454 (5)0.7379 (3)0.7859 (5)0.0606 (19)
H191.26930.77500.80760.073*
C201.1950 (5)0.7048 (3)0.8445 (5)0.0584 (18)
H201.18550.72100.90440.070*
C210.8421 (5)0.4808 (3)0.7978 (4)0.0476 (16)
H210.79770.46810.73840.057*
C220.8863 (4)0.5795 (3)0.8925 (4)0.0472 (16)
C230.8291 (4)0.5476 (3)0.8122 (4)0.0449 (15)
C240.7604 (5)0.5790 (3)0.7447 (5)0.0568 (18)
H240.72240.55860.69310.068*
C250.7488 (5)0.6406 (3)0.7547 (6)0.068 (2)
C260.8068 (5)0.6723 (3)0.8294 (6)0.071 (2)
H260.80110.71340.83340.086*
C270.8741 (5)0.6418 (3)0.8990 (5)0.0614 (19)
H270.91130.66300.95020.074*
C280.6559 (9)0.4070 (6)0.5211 (8)0.117 (4)
H280.61540.37470.51420.140*
C290.5455 (9)0.4509 (6)0.3801 (10)0.199 (7)
H29A0.51190.41500.38760.298*
H29B0.56190.45130.31530.298*
H29C0.50710.48470.38670.298*
C300.6919 (8)0.5047 (5)0.4636 (8)0.129 (4)
H30A0.74890.49690.51000.193*
H30B0.66140.53860.48560.193*
H30C0.70560.51260.39890.193*
C311.0027 (9)0.7059 (5)0.4841 (9)0.128 (3)
H311.05030.73400.49550.153*
C320.9706 (8)0.7371 (5)0.6416 (7)0.127 (3)
H32A0.98840.71380.70120.191*
H32B0.91450.75870.64460.191*
H32C1.01940.76470.63620.191*
C330.8992 (10)0.6434 (6)0.5505 (11)0.198 (5)
H33A0.83690.65120.51550.297*
H33B0.89760.63020.61700.297*
H33C0.92690.61310.51610.297*
C340.4033 (6)0.4034 (3)0.0944 (5)0.068 (2)
H340.34170.41050.06390.081*
C350.3825 (8)0.3037 (4)0.0193 (7)0.127 (4)
H35A0.32090.31880.00500.190*
H35B0.37880.26830.05780.190*
H35C0.41160.29450.03610.190*
C360.5326 (6)0.3332 (4)0.1312 (7)0.103 (3)
H36A0.56970.32620.08160.154*
H36B0.53100.29770.17010.154*
H36C0.55940.36510.17410.154*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Nd10.0450 (2)0.0465 (2)0.03667 (18)0.00268 (17)0.00517 (14)0.00282 (15)
O10.049 (3)0.050 (3)0.068 (3)0.004 (2)0.018 (2)0.007 (2)
O20.068 (3)0.050 (3)0.049 (3)0.001 (2)0.017 (2)0.003 (2)
O30.047 (3)0.045 (2)0.040 (2)0.003 (2)0.001 (2)0.0026 (18)
O40.129 (7)0.168 (7)0.116 (6)0.006 (5)0.015 (5)0.020 (5)
O50.231 (8)0.236 (8)0.191 (6)0.015 (6)0.082 (6)0.048 (6)
O60.078 (4)0.063 (3)0.104 (4)0.008 (3)0.002 (3)0.014 (3)
N10.047 (3)0.048 (3)0.042 (3)0.002 (3)0.008 (2)0.005 (2)
N20.040 (3)0.041 (3)0.041 (3)0.002 (2)0.006 (2)0.008 (2)
N30.052 (3)0.045 (3)0.038 (3)0.003 (2)0.010 (2)0.006 (2)
N40.057 (4)0.055 (3)0.042 (3)0.006 (3)0.008 (3)0.007 (2)
N50.101 (7)0.152 (8)0.072 (5)0.000 (6)0.003 (5)0.010 (5)
N60.124 (5)0.093 (4)0.115 (5)0.005 (4)0.038 (4)0.018 (4)
N70.083 (5)0.061 (4)0.068 (4)0.007 (3)0.002 (4)0.006 (3)
Br10.0759 (6)0.1142 (8)0.1206 (8)0.0082 (5)0.0388 (6)0.0435 (6)
Br20.0998 (7)0.0696 (5)0.0893 (6)0.0105 (5)0.0274 (5)0.0242 (4)
Br30.1152 (8)0.0817 (6)0.1245 (8)0.0199 (6)0.0330 (7)0.0376 (6)
C10.042 (4)0.048 (4)0.051 (4)0.002 (3)0.010 (3)0.001 (3)
C20.047 (4)0.049 (4)0.052 (4)0.003 (3)0.013 (3)0.006 (3)
C30.066 (5)0.063 (4)0.053 (4)0.003 (4)0.002 (4)0.004 (3)
C40.061 (5)0.065 (5)0.065 (5)0.008 (4)0.018 (4)0.010 (4)
C50.078 (6)0.054 (4)0.070 (5)0.001 (4)0.018 (4)0.020 (4)
C60.065 (5)0.061 (5)0.077 (5)0.003 (4)0.014 (4)0.017 (4)
C70.048 (4)0.043 (3)0.052 (4)0.009 (3)0.008 (3)0.001 (3)
C80.047 (4)0.046 (4)0.057 (4)0.004 (3)0.004 (3)0.012 (3)
C90.049 (4)0.046 (4)0.045 (4)0.004 (3)0.003 (3)0.009 (3)
C100.071 (5)0.042 (4)0.061 (4)0.002 (3)0.019 (4)0.004 (3)
C110.064 (5)0.044 (4)0.064 (4)0.001 (3)0.005 (4)0.009 (3)
C120.064 (5)0.063 (4)0.033 (3)0.009 (3)0.002 (3)0.007 (3)
C130.068 (5)0.066 (4)0.040 (3)0.010 (4)0.009 (3)0.012 (3)
C140.073 (5)0.068 (5)0.037 (4)0.003 (4)0.012 (4)0.001 (3)
C150.057 (5)0.050 (4)0.046 (4)0.008 (3)0.001 (3)0.004 (3)
C160.060 (5)0.050 (4)0.050 (4)0.000 (3)0.010 (3)0.005 (3)
C170.072 (5)0.064 (4)0.047 (4)0.004 (4)0.015 (4)0.004 (3)
C180.063 (5)0.057 (4)0.060 (4)0.002 (4)0.007 (4)0.016 (4)
C190.072 (5)0.043 (4)0.065 (5)0.002 (4)0.009 (4)0.007 (3)
C200.072 (5)0.052 (4)0.050 (4)0.008 (4)0.008 (4)0.000 (3)
C210.056 (4)0.052 (4)0.032 (3)0.005 (3)0.000 (3)0.004 (3)
C220.050 (4)0.042 (3)0.049 (4)0.002 (3)0.009 (3)0.005 (3)
C230.050 (4)0.043 (3)0.040 (3)0.004 (3)0.005 (3)0.004 (3)
C240.057 (5)0.063 (4)0.045 (4)0.004 (4)0.005 (3)0.004 (3)
C250.063 (5)0.058 (4)0.078 (5)0.004 (4)0.000 (4)0.018 (4)
C260.079 (6)0.039 (4)0.090 (6)0.005 (4)0.001 (5)0.007 (4)
C270.068 (5)0.045 (4)0.068 (5)0.002 (4)0.005 (4)0.006 (3)
C280.116 (10)0.164 (11)0.078 (7)0.033 (9)0.036 (7)0.039 (8)
C290.161 (13)0.227 (15)0.164 (12)0.055 (11)0.080 (10)0.009 (11)
C300.131 (10)0.120 (9)0.125 (9)0.021 (8)0.003 (8)0.019 (7)
C310.140 (6)0.117 (6)0.132 (6)0.012 (5)0.040 (5)0.015 (5)
C320.143 (7)0.123 (6)0.115 (6)0.015 (6)0.022 (6)0.009 (5)
C330.200 (9)0.201 (8)0.205 (8)0.080 (7)0.072 (7)0.001 (7)
C340.073 (5)0.058 (5)0.070 (5)0.007 (4)0.008 (4)0.011 (4)
C350.180 (11)0.069 (6)0.115 (8)0.020 (6)0.012 (8)0.022 (5)
C360.104 (8)0.084 (6)0.120 (8)0.017 (5)0.020 (6)0.017 (5)
Geometric parameters (Å, º) top
Nd1—O1i2.341 (4)C9—H9B0.9700
Nd1—O22.344 (4)C10—C111.512 (9)
Nd1—O32.448 (4)C10—H10A0.9700
Nd1—O3i2.467 (4)C10—H10B0.9700
Nd1—N1i2.616 (5)C11—H11A0.9700
Nd1—N2i2.864 (4)C11—H11B0.9700
Nd1—N32.896 (5)C12—C131.537 (9)
Nd1—N42.627 (5)C12—H12A0.9700
O1—C11.333 (7)C12—H12B0.9700
O1—Nd1i2.341 (4)C13—H13A0.9700
O2—C151.328 (8)C13—H13B0.9700
O3—C221.364 (7)C14—C161.459 (9)
O3—Nd1i2.467 (4)C14—H140.9300
O4—C281.227 (12)C15—C201.441 (9)
O5—C311.272 (12)C15—C161.442 (9)
O6—C341.217 (8)C16—C171.446 (9)
N1—C71.301 (7)C17—C181.388 (9)
N1—C81.494 (7)C17—H170.9300
N1—Nd1i2.616 (5)C18—C191.414 (9)
N2—C101.525 (7)C19—C201.401 (9)
N2—C91.527 (7)C19—H190.9300
N2—C211.533 (7)C20—H200.9300
N2—Nd1i2.864 (4)C21—C231.529 (8)
N3—C211.496 (8)C21—H210.9800
N3—C121.512 (7)C22—C271.415 (8)
N3—C111.533 (7)C22—C231.436 (8)
N4—C141.304 (8)C23—C241.415 (8)
N4—C131.492 (7)C24—C251.403 (9)
N5—C281.353 (13)C24—H240.9300
N5—C301.448 (12)C25—C261.391 (9)
N5—C291.483 (12)C26—C271.408 (9)
N6—C311.317 (12)C26—H260.9300
N6—C321.456 (11)C27—H270.9300
N6—C331.461 (13)C28—H280.9300
N7—C341.343 (9)C29—H29A0.9600
N7—C361.457 (9)C29—H29B0.9600
N7—C351.476 (9)C29—H29C0.9600
Br1—C41.928 (7)C30—H30A0.9600
Br2—C181.936 (7)C30—H30B0.9600
Br3—C251.933 (7)C30—H30C0.9600
C1—C61.435 (8)C31—H310.9300
C1—C21.453 (9)C32—H32A0.9600
C2—C31.414 (9)C32—H32B0.9600
C2—C71.471 (8)C32—H32C0.9600
C3—C41.409 (9)C33—H33A0.9600
C3—H30.9300C33—H33B0.9600
C4—C51.418 (9)C33—H33C0.9600
C5—C61.394 (10)C34—H340.9300
C5—H50.9300C35—H35A0.9600
C6—H60.9300C35—H35B0.9600
C7—H70.9300C35—H35C0.9600
C8—C91.531 (8)C36—H36A0.9600
C8—H8A0.9700C36—H36B0.9600
C8—H8B0.9700C36—H36C0.9600
C9—H9A0.9700
O1i—Nd1—O2132.23 (16)C10—C11—H11A110.3
O1i—Nd1—O3141.78 (14)N3—C11—H11A110.3
O2—Nd1—O383.19 (14)C10—C11—H11B110.3
O1i—Nd1—O3i82.36 (14)N3—C11—H11B110.3
O2—Nd1—O3i143.18 (14)H11A—C11—H11B108.5
O3—Nd1—O3i68.98 (14)N3—C12—C13113.0 (5)
O1i—Nd1—N1i70.04 (15)N3—C12—H12A109.0
O2—Nd1—N1i76.54 (15)C13—C12—H12A109.0
O3—Nd1—N1i143.92 (14)N3—C12—H12B109.0
O3i—Nd1—N1i112.44 (14)C13—C12—H12B109.0
O1i—Nd1—N475.43 (15)H12A—C12—H12B107.8
O2—Nd1—N470.15 (15)N4—C13—C12108.2 (5)
O3—Nd1—N4112.86 (14)N4—C13—H13A110.0
O3i—Nd1—N4142.50 (14)C12—C13—H13A110.0
N1i—Nd1—N487.97 (16)N4—C13—H13B110.0
O1i—Nd1—N2i111.02 (14)C12—C13—H13B110.0
O2—Nd1—N2i83.34 (14)H13A—C13—H13B108.4
O3—Nd1—N2i83.07 (13)N4—C14—C16125.9 (6)
O3i—Nd1—N2i70.15 (13)N4—C14—H14117.1
N1i—Nd1—N2i65.33 (14)C16—C14—H14117.1
N4—Nd1—N2i146.32 (15)O2—C15—C20120.1 (6)
O1i—Nd1—N382.21 (14)O2—C15—C16123.5 (6)
O2—Nd1—N3110.68 (14)C20—C15—C16116.4 (6)
O3—Nd1—N369.76 (13)C15—C16—C17120.0 (6)
O3i—Nd1—N382.46 (13)C15—C16—C14123.1 (6)
N1i—Nd1—N3145.60 (14)C17—C16—C14116.8 (6)
N4—Nd1—N365.05 (15)C18—C17—C16121.0 (6)
N2i—Nd1—N3146.97 (14)C18—C17—H17119.5
O1i—Nd1—Nd1i113.20 (11)C16—C17—H17119.5
O2—Nd1—Nd1i114.57 (11)C17—C18—C19119.9 (6)
O3—Nd1—Nd1i34.64 (9)C17—C18—Br2118.9 (5)
O3i—Nd1—Nd1i34.34 (9)C19—C18—Br2121.2 (5)
N1i—Nd1—Nd1i136.13 (11)C20—C19—C18120.0 (6)
N4—Nd1—Nd1i135.87 (12)C20—C19—H19120.0
N2i—Nd1—Nd1i73.76 (10)C18—C19—H19120.0
N3—Nd1—Nd1i73.20 (10)C19—C20—C15122.5 (6)
C1—O1—Nd1i136.9 (4)C19—C20—H20118.7
C15—O2—Nd1135.7 (4)C15—C20—H20118.7
C22—O3—Nd1120.3 (4)N3—C21—C23114.6 (5)
C22—O3—Nd1i120.0 (4)N3—C21—N2105.6 (4)
Nd1—O3—Nd1i111.02 (14)C23—C21—N2111.8 (5)
C7—N1—C8117.1 (5)N3—C21—H21108.2
C7—N1—Nd1i130.1 (4)C23—C21—H21108.2
C8—N1—Nd1i112.8 (4)N2—C21—H21108.2
C10—N2—C9111.6 (4)O3—C22—C27120.3 (5)
C10—N2—C21102.1 (4)O3—C22—C23121.0 (5)
C9—N2—C21108.6 (4)C27—C22—C23118.7 (6)
C10—N2—Nd1i107.0 (3)C24—C23—C22118.9 (6)
C9—N2—Nd1i108.6 (3)C24—C23—C21119.8 (5)
C21—N2—Nd1i118.9 (3)C22—C23—C21121.3 (5)
C21—N3—C12108.8 (5)C25—C24—C23120.9 (6)
C21—N3—C11102.9 (5)C25—C24—H24119.6
C12—N3—C11112.4 (5)C23—C24—H24119.6
C21—N3—Nd1118.6 (3)C26—C25—C24120.6 (6)
C12—N3—Nd1108.3 (4)C26—C25—Br3120.2 (5)
C11—N3—Nd1105.8 (3)C24—C25—Br3119.2 (5)
C14—N4—C13117.8 (5)C25—C26—C27119.6 (6)
C14—N4—Nd1129.4 (4)C25—C26—H26120.2
C13—N4—Nd1112.8 (4)C27—C26—H26120.2
C28—N5—C30119.7 (9)C26—C27—C22121.2 (6)
C28—N5—C29120.8 (11)C26—C27—H27119.4
C30—N5—C29119.4 (10)C22—C27—H27119.4
C31—N6—C32119.4 (10)O4—C28—N5126.5 (11)
C31—N6—C33116.9 (10)O4—C28—H28116.7
C32—N6—C33122.9 (10)N5—C28—H28116.7
C34—N7—C36121.1 (7)N5—C29—H29A109.5
C34—N7—C35121.2 (7)N5—C29—H29B109.5
C36—N7—C35117.6 (7)H29A—C29—H29B109.5
O1—C1—C6120.1 (6)N5—C29—H29C109.5
O1—C1—C2122.9 (5)H29A—C29—H29C109.5
C6—C1—C2117.0 (6)H29B—C29—H29C109.5
C3—C2—C1119.5 (6)N5—C30—H30A109.5
C3—C2—C7118.1 (6)N5—C30—H30B109.5
C1—C2—C7122.2 (6)H30A—C30—H30B109.5
C4—C3—C2122.2 (7)N5—C30—H30C109.5
C4—C3—H3118.9H30A—C30—H30C109.5
C2—C3—H3118.9H30B—C30—H30C109.5
C3—C4—C5118.4 (7)O5—C31—N6125.3 (12)
C3—C4—Br1121.0 (6)O5—C31—H31117.3
C5—C4—Br1120.6 (5)N6—C31—H31117.3
C6—C5—C4120.8 (6)N6—C32—H32A109.5
C6—C5—H5119.6N6—C32—H32B109.5
C4—C5—H5119.6H32A—C32—H32B109.5
C5—C6—C1122.0 (7)N6—C32—H32C109.5
C5—C6—H6119.0H32A—C32—H32C109.5
C1—C6—H6119.0H32B—C32—H32C109.5
N1—C7—C2126.6 (6)N6—C33—H33A109.5
N1—C7—H7116.7N6—C33—H33B109.5
C2—C7—H7116.7H33A—C33—H33B109.5
N1—C8—C9107.7 (5)N6—C33—H33C109.5
N1—C8—H8A110.2H33A—C33—H33C109.5
C9—C8—H8A110.2H33B—C33—H33C109.5
N1—C8—H8B110.2O6—C34—N7125.4 (7)
C9—C8—H8B110.2O6—C34—H34117.3
H8A—C8—H8B108.5N7—C34—H34117.3
N2—C9—C8112.8 (5)N7—C35—H35A109.5
N2—C9—H9A109.0N7—C35—H35B109.5
C8—C9—H9A109.0H35A—C35—H35B109.5
N2—C9—H9B109.0N7—C35—H35C109.5
C8—C9—H9B109.0H35A—C35—H35C109.5
H9A—C9—H9B107.8H35B—C35—H35C109.5
C11—C10—N2107.0 (5)N7—C36—H36A109.5
C11—C10—H10A110.3N7—C36—H36B109.5
N2—C10—H10A110.3H36A—C36—H36B109.5
C11—C10—H10B110.3N7—C36—H36C109.5
N2—C10—H10B110.3H36A—C36—H36C109.5
H10A—C10—H10B108.6H36B—C36—H36C109.5
C10—C11—N3107.3 (5)
O1i—Nd1—O2—C157.2 (6)C3—C2—C7—N1170.8 (6)
O3—Nd1—O2—C15156.6 (5)C1—C2—C7—N114.0 (10)
O3i—Nd1—O2—C15163.1 (5)C7—N1—C8—C9117.0 (6)
N1i—Nd1—O2—C1553.5 (5)Nd1i—N1—C8—C960.6 (5)
N4—Nd1—O2—C1539.2 (5)C10—N2—C9—C885.1 (6)
N2i—Nd1—O2—C15119.7 (5)C21—N2—C9—C8163.2 (4)
N3—Nd1—O2—C1591.2 (5)Nd1i—N2—C9—C832.6 (5)
Nd1i—Nd1—O2—C15171.6 (5)N1—C8—C9—N262.4 (6)
O1i—Nd1—O3—C22103.7 (4)C9—N2—C10—C11139.9 (5)
O2—Nd1—O3—C2256.8 (4)C21—N2—C10—C1124.1 (6)
O3i—Nd1—O3—C22147.8 (5)Nd1i—N2—C10—C11101.5 (5)
N1i—Nd1—O3—C22112.6 (4)N2—C10—C11—N32.2 (6)
N4—Nd1—O3—C228.3 (4)C21—N3—C11—C1021.2 (6)
N2i—Nd1—O3—C22140.9 (4)C12—N3—C11—C10138.1 (5)
N3—Nd1—O3—C2258.2 (4)Nd1—N3—C11—C10103.9 (5)
Nd1i—Nd1—O3—C22147.8 (5)C21—N3—C12—C13163.0 (5)
O1i—Nd1—O3—Nd1i44.1 (3)C11—N3—C12—C1383.7 (6)
O2—Nd1—O3—Nd1i155.44 (16)Nd1—N3—C12—C1332.8 (6)
O3i—Nd1—O3—Nd1i0.0C14—N4—C13—C12118.4 (6)
N1i—Nd1—O3—Nd1i99.6 (2)Nd1—N4—C13—C1260.2 (6)
N4—Nd1—O3—Nd1i139.49 (15)N3—C12—C13—N462.7 (7)
N2i—Nd1—O3—Nd1i71.36 (15)C13—N4—C14—C16173.0 (6)
N3—Nd1—O3—Nd1i89.54 (16)Nd1—N4—C14—C165.3 (10)
O1i—Nd1—N3—C21156.1 (4)Nd1—O2—C15—C20145.5 (5)
O2—Nd1—N3—C2171.6 (4)Nd1—O2—C15—C1635.8 (9)
O3—Nd1—N3—C212.5 (4)O2—C15—C16—C17179.6 (6)
O3i—Nd1—N3—C2172.8 (4)C20—C15—C16—C171.7 (9)
N1i—Nd1—N3—C21168.0 (3)O2—C15—C16—C143.9 (10)
N4—Nd1—N3—C21126.4 (4)C20—C15—C16—C14174.8 (6)
N2i—Nd1—N3—C2139.1 (5)N4—C14—C16—C1516.1 (11)
Nd1i—Nd1—N3—C2138.9 (3)N4—C14—C16—C17167.3 (7)
O1i—Nd1—N3—C1279.4 (4)C15—C16—C17—C181.5 (10)
O2—Nd1—N3—C1252.9 (4)C14—C16—C17—C18178.2 (6)
O3—Nd1—N3—C12127.0 (4)C16—C17—C18—C193.6 (10)
O3i—Nd1—N3—C12162.7 (4)C16—C17—C18—Br2176.0 (5)
N1i—Nd1—N3—C1243.5 (5)C17—C18—C19—C202.4 (10)
N4—Nd1—N3—C121.9 (4)Br2—C18—C19—C20177.2 (5)
N2i—Nd1—N3—C12163.6 (3)C18—C19—C20—C151.0 (10)
Nd1i—Nd1—N3—C12163.4 (4)O2—C15—C20—C19178.3 (6)
O1i—Nd1—N3—C1141.3 (4)C16—C15—C20—C192.9 (10)
O2—Nd1—N3—C11173.6 (4)C12—N3—C21—C2380.3 (6)
O3—Nd1—N3—C11112.3 (4)C11—N3—C21—C23160.4 (5)
O3i—Nd1—N3—C1142.0 (4)Nd1—N3—C21—C2344.0 (5)
N1i—Nd1—N3—C1177.3 (4)C12—N3—C21—N2156.3 (4)
N4—Nd1—N3—C11118.8 (4)C11—N3—C21—N236.9 (5)
N2i—Nd1—N3—C1175.7 (4)Nd1—N3—C21—N279.4 (4)
Nd1i—Nd1—N3—C1175.9 (3)C10—N2—C21—N338.3 (5)
O1i—Nd1—N4—C14123.5 (6)C9—N2—C21—N3156.2 (4)
O2—Nd1—N4—C1422.8 (6)Nd1i—N2—C21—N379.1 (4)
O3—Nd1—N4—C1496.0 (6)C10—N2—C21—C23163.5 (5)
O3i—Nd1—N4—C14179.2 (5)C9—N2—C21—C2378.5 (5)
N1i—Nd1—N4—C1453.6 (6)Nd1i—N2—C21—C2346.2 (6)
N2i—Nd1—N4—C1417.4 (7)Nd1—O3—C22—C27105.6 (6)
N3—Nd1—N4—C14148.4 (6)Nd1i—O3—C22—C27109.5 (6)
Nd1i—Nd1—N4—C14128.0 (5)Nd1—O3—C22—C2373.8 (7)
O1i—Nd1—N4—C1358.1 (4)Nd1i—O3—C22—C2371.1 (6)
O2—Nd1—N4—C13155.6 (5)O3—C22—C23—C24178.3 (6)
O3—Nd1—N4—C1382.4 (4)C27—C22—C23—C242.3 (9)
O3i—Nd1—N4—C132.5 (5)O3—C22—C23—C212.6 (9)
N1i—Nd1—N4—C13128.0 (4)C27—C22—C23—C21176.8 (6)
N2i—Nd1—N4—C13164.3 (4)N3—C21—C23—C24121.4 (6)
N3—Nd1—N4—C1330.0 (4)N2—C21—C23—C24118.5 (6)
Nd1i—Nd1—N4—C1350.3 (5)N3—C21—C23—C2257.7 (7)
Nd1i—O1—C1—C6144.0 (5)N2—C21—C23—C2262.5 (7)
Nd1i—O1—C1—C237.2 (9)C22—C23—C24—C250.9 (10)
O1—C1—C2—C3176.0 (6)C21—C23—C24—C25178.2 (6)
C6—C1—C2—C32.9 (9)C23—C24—C25—C262.1 (11)
O1—C1—C2—C70.9 (9)C23—C24—C25—Br3179.1 (5)
C6—C1—C2—C7178.0 (6)C24—C25—C26—C273.6 (12)
C1—C2—C3—C43.6 (10)Br3—C25—C26—C27177.6 (6)
C7—C2—C3—C4178.9 (6)C25—C26—C27—C222.2 (12)
C2—C3—C4—C51.8 (10)O3—C22—C27—C26179.8 (6)
C2—C3—C4—Br1177.1 (5)C23—C22—C27—C260.7 (10)
C3—C4—C5—C60.5 (11)C30—N5—C28—O40.9 (17)
Br1—C4—C5—C6179.5 (6)C29—N5—C28—O4178.1 (12)
C4—C5—C6—C11.1 (11)C32—N6—C31—O5173.4 (12)
O1—C1—C6—C5178.3 (6)C33—N6—C31—O517.0 (19)
C2—C1—C6—C50.6 (10)C36—N7—C34—O62.7 (12)
C8—N1—C7—C2172.8 (6)C35—N7—C34—O6176.7 (8)
Nd1i—N1—C7—C24.4 (9)
Symmetry code: (i) x+2, y+1, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C21—H21···O40.982.583.514 (10)159

Experimental details

Crystal data
Chemical formula[Nd2(C27H24Br3N4O3)2]·6C3H7NO
Mr2111.46
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)14.624 (6), 22.460 (4), 13.663 (4)
β (°) 101.133 (6)
V3)4403 (2)
Z2
Radiation typeMo Kα
µ (mm1)3.95
Crystal size (mm)0.25 × 0.23 × 0.22
Data collection
DiffractometerBruke APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.438, 0.477
No. of measured, independent and
observed [I > 2σ(I)] reflections
25933, 8078, 5119
Rint0.057
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.120, 1.02
No. of reflections8078
No. of parameters484
No. of restraints62
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.84, 0.78

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top
Nd1—O1i2.341 (4)Nd1—N1i2.616 (5)
Nd1—O22.344 (4)Nd1—N2i2.864 (4)
Nd1—O32.448 (4)Nd1—N32.896 (5)
Nd1—O3i2.467 (4)Nd1—N42.627 (5)
Symmetry code: (i) x+2, y+1, z+2.
 

Acknowledgements

This work was supported by the Education Department Foundation of Fujian Province of China (grant Nos. JA08212 and 2008 F5053).

References

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First citationBruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
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