supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportsimilar papers Open access

hy2250 scheme

Acta Cryst. (2009). E65, m1660    [ doi:10.1107/S1600536809047564 ]

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

Q.-F. Xie, M.-L. Huang and Y.-M. Chen

Abstract top

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.

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 m−3
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 mm−1
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)
graphiteRint = 0.057
φ and ω scansθmax = 25.5°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −17→13
Tmin = 0.438, Tmax = 0.477k = −27→27
25933 measured reflectionsl = −16→16
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 Å−3
62 restraintsΔρmin = −0.78 e Å−3
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 mm−1
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 reflectionsθmax = 25.5°
Refinement top
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.120Δρmax = 0.84 e Å−3
S = 1.02Δρmin = −0.78 e Å−3
8078 reflectionsAbsolute structure: ?
484 parametersFlack parameter: ?
62 restraintsRogers parameter: ?
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)
H35A0.32090.3188−0.00500.190*
H35B0.37880.26830.05780.190*
H35C0.41160.2945−0.03610.190*
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, °) 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—N1−170.8 (6)
O3—Nd1—O2—C15−156.6 (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—C9−60.6 (5)
N4—Nd1—O2—C15−39.2 (5)C10—N2—C9—C885.1 (6)
N2i—Nd1—O2—C15119.7 (5)C21—N2—C9—C8−163.2 (4)
N3—Nd1—O2—C15−91.2 (5)Nd1i—N2—C9—C8−32.6 (5)
Nd1i—Nd1—O2—C15−171.6 (5)N1—C8—C9—N262.4 (6)
O1i—Nd1—O3—C22−103.7 (4)C9—N2—C10—C11139.9 (5)
O2—Nd1—O3—C2256.8 (4)C21—N2—C10—C1124.1 (6)
O3i—Nd1—O3—C22−147.8 (5)Nd1i—N2—C10—C11−101.5 (5)
N1i—Nd1—O3—C22112.6 (4)N2—C10—C11—N3−2.2 (6)
N4—Nd1—O3—C22−8.3 (4)C21—N3—C11—C10−21.2 (6)
N2i—Nd1—O3—C22140.9 (4)C12—N3—C11—C10−138.1 (5)
N3—Nd1—O3—C22−58.2 (4)Nd1—N3—C11—C10103.9 (5)
Nd1i—Nd1—O3—C22−147.8 (5)C21—N3—C12—C13163.0 (5)
O1i—Nd1—O3—Nd1i44.1 (3)C11—N3—C12—C13−83.7 (6)
O2—Nd1—O3—Nd1i−155.44 (16)Nd1—N3—C12—C1332.8 (6)
O3i—Nd1—O3—Nd1i0.0C14—N4—C13—C12−118.4 (6)
N1i—Nd1—O3—Nd1i−99.6 (2)Nd1—N4—C13—C1260.2 (6)
N4—Nd1—O3—Nd1i139.49 (15)N3—C12—C13—N4−62.7 (7)
N2i—Nd1—O3—Nd1i−71.36 (15)C13—N4—C14—C16173.0 (6)
N3—Nd1—O3—Nd1i89.54 (16)Nd1—N4—C14—C16−5.3 (10)
O1i—Nd1—N3—C21156.1 (4)Nd1—O2—C15—C20−145.5 (5)
O2—Nd1—N3—C21−71.6 (4)Nd1—O2—C15—C1635.8 (9)
O3—Nd1—N3—C212.5 (4)O2—C15—C16—C17−179.6 (6)
O3i—Nd1—N3—C2172.8 (4)C20—C15—C16—C171.7 (9)
N1i—Nd1—N3—C21−168.0 (3)O2—C15—C16—C143.9 (10)
N4—Nd1—N3—C21−126.4 (4)C20—C15—C16—C14−174.8 (6)
N2i—Nd1—N3—C2139.1 (5)N4—C14—C16—C15−16.1 (11)
Nd1i—Nd1—N3—C2138.9 (3)N4—C14—C16—C17167.3 (7)
O1i—Nd1—N3—C12−79.4 (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—C19−3.6 (10)
O3i—Nd1—N3—C12−162.7 (4)C16—C17—C18—Br2176.0 (5)
N1i—Nd1—N3—C12−43.5 (5)C17—C18—C19—C202.4 (10)
N4—Nd1—N3—C12−1.9 (4)Br2—C18—C19—C20−177.2 (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—C19−2.9 (10)
O2—Nd1—N3—C11173.6 (4)C12—N3—C21—C23−80.3 (6)
O3—Nd1—N3—C11−112.3 (4)C11—N3—C21—C23160.4 (5)
O3i—Nd1—N3—C11−42.0 (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—C11−75.7 (4)Nd1—N3—C21—N2−79.4 (4)
Nd1i—Nd1—N3—C11−75.9 (3)C10—N2—C21—N3−38.3 (5)
O1i—Nd1—N4—C14−123.5 (6)C9—N2—C21—N3−156.2 (4)
O2—Nd1—N4—C1422.8 (6)Nd1i—N2—C21—N379.1 (4)
O3—Nd1—N4—C1496.0 (6)C10—N2—C21—C23−163.5 (5)
O3i—Nd1—N4—C14−179.2 (5)C9—N2—C21—C2378.5 (5)
N1i—Nd1—N4—C14−53.6 (6)Nd1i—N2—C21—C23−46.2 (6)
N2i—Nd1—N4—C14−17.4 (7)Nd1—O3—C22—C27−105.6 (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—C23−71.1 (6)
O2—Nd1—N4—C13−155.6 (5)O3—C22—C23—C24178.3 (6)
O3—Nd1—N4—C13−82.4 (4)C27—C22—C23—C24−2.3 (9)
O3i—Nd1—N4—C132.5 (5)O3—C22—C23—C21−2.6 (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—C13−30.0 (4)N2—C21—C23—C24−118.5 (6)
Nd1i—Nd1—N4—C13−50.3 (5)N3—C21—C23—C22−57.7 (7)
Nd1i—O1—C1—C6144.0 (5)N2—C21—C23—C2262.5 (7)
Nd1i—O1—C1—C2−37.2 (9)C22—C23—C24—C250.9 (10)
O1—C1—C2—C3−176.0 (6)C21—C23—C24—C25−178.2 (6)
C6—C1—C2—C32.9 (9)C23—C24—C25—C262.1 (11)
O1—C1—C2—C7−0.9 (9)C23—C24—C25—Br3−179.1 (5)
C6—C1—C2—C7178.0 (6)C24—C25—C26—C27−3.6 (12)
C1—C2—C3—C4−3.6 (10)Br3—C25—C26—C27177.6 (6)
C7—C2—C3—C4−178.9 (6)C25—C26—C27—C222.2 (12)
C2—C3—C4—C51.8 (10)O3—C22—C27—C26−179.8 (6)
C2—C3—C4—Br1−177.1 (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—C1−1.1 (11)C32—N6—C31—O5−173.4 (12)
O1—C1—C6—C5178.3 (6)C33—N6—C31—O517.0 (19)
C2—C1—C6—C5−0.6 (10)C36—N7—C34—O62.7 (12)
C8—N1—C7—C2−172.8 (6)C35—N7—C34—O6−176.7 (8)
Nd1i—N1—C7—C24.4 (9)
Symmetry codes: (i) −x+2, −y+1, −z+2.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C21—H21···O40.982.583.514 (10)159
Table 1
Selected geometric parameters (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 codes: (i) −x+2, −y+1, −z+2.
Acknowledgements top

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

references
References top

Bian, Z. Y., Sumi, K., Furue, M., Sato, S., Koike, K. & Ishitani, O. (2008). Inorg. Chem. 47, 10801–10803.

Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Fondo, M., Deibe, A. M. G., Ocampo, N., Bermejo, M. R. & Sanmartín, J. (2005). Z. Anorg. Allg. Chem. 631, 2041–2045.

Palaniandavar, M., Velusamy, M. & Mayilmurugan, R. (2006). J. Chem. Sci. 118, 601–610.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Velusamy, M., Mayilmurugan, R. & Palaniandavar, M. (2004). Inorg. Chem. 43, 6284–6293.

Xie, Q.-F., Huang, M.-L. & Chen, Y.-M. (2009). Chin. J. Inorg. Chem. 25, 1539–1544.

Yang, L.-W., Liu, S., Wong, E., Rettig, S. J. & Orvig, C. (1995). Inorg. Chem. 34, 2164–2178.