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Acta Cryst. (2007). E63, m1595    [ doi:10.1107/S160053680702154X ]

catena-Poly[[aqua[(2,4-dichlorophenoxy)acetato]neodymium(III)]-di-[mu]-(2,4-dichlorophenoxy)acetato]

J. Guo, W.-J. Liang and W.-D. Song

Abstract top

The title complex, [Nd(C8H5Cl2O3)3(H2O)]n, is a neodymium polymer based on the flexible 2,4-dichlorophenoxyacetate ligand. The NdII center is coordinated by eight O atoms from five 2,4-dichlorophenoxyacetate ligands and one water molecule, and displays a distorted tricapped trigonal-prismatic geometry. The Nd centers are linked by the (2,4-dichlorophenoxy)acetate ligands via two bridging carboxylate O atoms, with an Nd...Nd distance of 4.172 (3) Å, forming chains along the c axis. The chains are assembled into ruffled layers via [pi]-[pi] stacking interactions; the centroid-centroid and offset distances between phenyl groups [at (-1 + x, y, -1 + z)] are 3.719 (2) and 0.060 (2) Å, respectively, indicating a normal [pi]-[pi] stacking interaction.

Comment top

2,4-Dichlorophenoxyacetic acid is an important biologically active compound that has been commonly used in herbicides and plant-growth agents. The monophenoxyacetate group has versatile bonding modes to metal ions and easily forms simple complexes (Dendrinou-Samara et al., 2001; Psomas et al., 2000). Recently, we obtained the one-dimensional neodymium polymer (I), its crystal structure is reported here.

The NdIII centre is in a distorted tricapped trigonal prismatic geometry, defined by eight O atoms from five 2,4-dichlorophenoxyacetate ligands and one water molecule (Fig. 1). Coordination bond lengths, angles and torsion angles at the NdIII atom are given in Table 1. The 2,4-dichlorophenoxyacetate ligands exhibit two different types of coordination modes: One of the ligands is coordinating only to one of the neodymium centers (O7, O8), the other two carboxylate ligands are linking the neodym centers in a µ2 way via the carboxylate atoms

O2 and O4 to form chains parallel to the c axis with a Nd···Nd distance of 4.172 (3) Å. The oxygen atoms of the non-bridging 2,4-dichlorophenoxyacetate ligand are forming hydrogen bonds with the coordinated water molecules of neighboring entities with the H-bonds extending parallel to the main polymeric chain (see Table 2 for numerical values). The chains as a whole are also involved in π···π stacking interactions of some of the phenyl rings (C11 to C16) with neigboring chains to form a ruffly layer perpendicular to the b axis (Fig. 2). The centroid-centroid distance between phenyl groups (at -1 + x, y, -1 + z) and the offset are 3.719 (2) and 0.060 (2) Å, respectively, indicating a normal π···π stacking interaction (Lee et al., 2007).

Related literature top

Related literature: Dendrinou-Samara et al. (2001); Lee et al. (2007); Psomas et al. (2000).

Experimental top

A mixture of Nd2O3 (0.5 mmol), 2,4-dichlorophenoxyacetic acid (1 mmol) and H2O (10 ml) in the presence of HClO4 (0.385 mmol) was stirred vigorously for 20 min and then sealed in a Teflon-lined stainless-steel autoclave (20 ml, capacity). The autoclave was heated to and maintained at 433 K for 7 days, and then cooled to room temperature at 5 K h-1. The crystal were obtained in ca 46% yield based on Nd.

Refinement top

Carbon-bound H atoms were placed at calculated positions and were treated as riding on the parent C atoms with C—H = 0.93 Å, and with Uiso(H) = 1.2 Ueq(C). Water H atoms were tentatively located in difference Fourier maps and were refined with distance restraints of O–H = 0.85 Å and H···H = 1.39 Å, each within a standard deviation of 0.01 Å

Computing details top

Data collection: APEXII (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2004); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The structure of (I), showing the atom-numbering scheme and displacement ellipsoids drawn at the 30% probability level. Unlabeled atoms are related to the labelled atoms by the symmetry operator (x, 0.5 - y, -1/2 + z).
[Figure 2] Fig. 2. A packing view of (I) along the c axis. Hydrogen bonds are depicted as broken lines.
catena-Poly[[aqua[(2,4-dichlorophenoxy)acetato]neodymium(III)]-di-µ-\ (2,4-dichlorophenoxy)acetato] top
Crystal data top
[Nd(C8H5Cl2O3)3(H2O)]F(000) = 1612
Mr = 822.32Dx = 1.871 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 8000 reflections
a = 10.1801 (2) Åθ = 1.7–26.0°
b = 35.4768 (6) ŵ = 2.38 mm−1
c = 8.1456 (2) ÅT = 293 K
β = 97.144 (1)°Platelet, purple
V = 2919.00 (10) Å30.25 × 0.20 × 0.20 mm
Z = 4
Data collection top
Bruker APEXII area-detector
diffractometer		5617 independent reflections
Radiation source: fine-focus sealed tube5062 reflections with I > 2σ(I)
graphiteRint = 0.038
φ and ω scansθmax = 26.0°, θmin = 1.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −12→12
Tmin = 0.566, Tmax = 0.626k = −43→43
31522 measured reflectionsl = −10→8
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)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088H atoms treated by a mixture of independent and constrained refinement
S = 1.23 w = 1/[σ2(Fo2) + (0.0401P)2 + 2.8846P]
where P = (Fo2 + 2Fc2)/3
5617 reflections(Δ/σ)max = 0.001
370 parametersΔρmax = 0.74 e Å−3
3 restraintsΔρmin = −1.54 e Å−3
Crystal data top
[Nd(C8H5Cl2O3)3(H2O)]V = 2919.00 (10) Å3
Mr = 822.32Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.1801 (2) ŵ = 2.38 mm−1
b = 35.4768 (6) ÅT = 293 K
c = 8.1456 (2) Å0.25 × 0.20 × 0.20 mm
β = 97.144 (1)°
Data collection top
Bruker APEXII area-detector
diffractometer		5617 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		5062 reflections with I > 2σ(I)
Tmin = 0.566, Tmax = 0.626Rint = 0.038
31522 measured reflectionsθmax = 26.0°
Refinement top
R[F2 > 2σ(F2)] = 0.031H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.088Δρmax = 0.74 e Å−3
S = 1.23Δρmin = −1.54 e Å−3
5617 reflectionsAbsolute structure: ?
370 parametersFlack parameter: ?
3 restraintsRogers parameter: ?
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.2331 (3)0.23189 (10)0.4591 (5)0.0211 (8)
C20.1116 (4)0.22703 (12)0.3335 (5)0.0310 (9)
H2A0.07520.25160.30220.037*
H2B0.13700.21510.23500.037*
C30.0273 (4)0.16667 (11)0.3963 (5)0.0284 (8)
C40.1374 (4)0.14754 (13)0.3584 (6)0.0456 (12)
H40.21180.16090.33590.055*
C50.1378 (5)0.10843 (14)0.3535 (8)0.0592 (15)
H50.21190.09570.32600.071*
C60.0302 (5)0.08870 (13)0.3888 (8)0.0546 (13)
C7−0.0803 (4)0.10688 (13)0.4312 (7)0.0470 (12)
H7−0.15300.09320.45700.056*
C8−0.0809 (4)0.14578 (12)0.4346 (5)0.0337 (9)
C90.7044 (3)0.22777 (10)0.9310 (5)0.0234 (8)
C100.8244 (4)0.22184 (12)1.0600 (5)0.0300 (9)
H10A0.86020.24621.09700.036*
H10B0.79690.20891.15500.036*
C110.9044 (4)0.16244 (11)0.9735 (5)0.0298 (9)
C120.7919 (4)0.14320 (13)1.0026 (6)0.0422 (11)
H120.72190.15631.03890.051*
C130.7817 (5)0.10486 (15)0.9785 (7)0.0569 (14)
H130.70570.09231.00030.068*
C140.8829 (6)0.08520 (14)0.9227 (8)0.0597 (15)
C150.9975 (5)0.10342 (14)0.8931 (7)0.0536 (13)
H151.06690.09000.85690.064*
C161.0074 (4)0.14191 (13)0.9182 (6)0.0400 (10)
C170.4793 (3)0.15799 (11)0.6587 (5)0.0292 (9)
C180.5042 (5)0.11663 (12)0.6386 (6)0.0456 (11)
H18A0.59410.11050.68510.055*
H18B0.44400.10210.69720.055*
C190.5380 (4)0.07433 (12)0.4211 (6)0.0426 (11)
C200.6068 (5)0.04845 (12)0.5265 (7)0.0518 (13)
H200.61820.05280.63990.062*
C210.6589 (5)0.01595 (14)0.4636 (9)0.0635 (16)
H210.7055−0.00120.53480.076*
C220.6413 (6)0.00947 (13)0.2979 (9)0.0632 (16)
C230.5724 (6)0.03446 (14)0.1902 (8)0.0604 (15)
H230.56050.02970.07700.072*
C240.5212 (5)0.06667 (13)0.2532 (7)0.0493 (12)
Cl1−0.21982 (12)0.16884 (4)0.4836 (2)0.0636 (4)
Cl20.02712 (19)0.03967 (4)0.3748 (3)0.1027 (7)
Cl31.15126 (13)0.16473 (4)0.8836 (2)0.0710 (4)
Cl40.8703 (2)0.03676 (4)0.8933 (3)0.1017 (7)
Cl50.43592 (16)0.09847 (4)0.11576 (19)0.0678 (4)
Cl60.7043 (2)−0.03135 (4)0.2194 (3)0.1014 (7)
Nd10.469125 (17)0.237244 (5)0.69698 (2)0.01875 (8)
O10.2348 (2)0.21996 (8)0.6017 (3)0.0319 (6)
O20.3345 (2)0.24889 (8)0.4157 (3)0.0265 (6)
O30.0130 (2)0.20488 (7)0.3960 (4)0.0309 (6)
O40.6009 (3)0.24198 (8)0.9835 (3)0.0290 (4)
O50.7074 (2)0.22086 (8)0.7852 (3)0.0290 (4)
O60.9254 (2)0.20022 (8)0.9956 (3)0.0318 (6)
O70.4680 (3)0.17038 (8)0.8010 (4)0.0334 (6)
O80.4773 (3)0.17940 (7)0.5340 (3)0.0320 (6)
O90.4849 (3)0.10728 (8)0.4683 (4)0.0457 (8)
O1W0.4630 (4)0.30741 (9)0.7056 (4)0.0515 (9)
H1W0.469 (6)0.3196 (12)0.790 (3)0.062*
H2W0.459 (6)0.3203 (12)0.623 (3)0.062*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0169 (16)0.0262 (18)0.019 (2)−0.0013 (13)−0.0007 (13)−0.0043 (15)
C20.0232 (18)0.038 (2)0.030 (2)−0.0101 (15)−0.0027 (16)0.0029 (18)
C30.0244 (17)0.036 (2)0.023 (2)−0.0037 (15)−0.0033 (15)−0.0031 (17)
C40.028 (2)0.047 (3)0.063 (3)−0.0041 (18)0.007 (2)−0.008 (2)
C50.039 (3)0.050 (3)0.089 (5)0.009 (2)0.015 (3)−0.014 (3)
C60.052 (3)0.035 (3)0.076 (4)0.002 (2)0.005 (3)−0.002 (3)
C70.038 (2)0.043 (3)0.061 (3)−0.0049 (19)0.012 (2)0.007 (2)
C80.031 (2)0.039 (2)0.032 (3)−0.0024 (16)0.0099 (17)0.0012 (19)
C90.0224 (17)0.0220 (17)0.026 (2)−0.0018 (13)0.0043 (15)0.0018 (15)
C100.0260 (18)0.038 (2)0.024 (2)0.0082 (16)−0.0042 (15)−0.0044 (17)
C110.0283 (18)0.038 (2)0.023 (2)0.0069 (16)0.0002 (15)0.0042 (17)
C120.033 (2)0.048 (3)0.046 (3)0.0035 (18)0.0047 (19)0.005 (2)
C130.047 (3)0.054 (3)0.069 (4)−0.005 (2)0.005 (2)0.010 (3)
C140.076 (4)0.035 (3)0.065 (4)0.003 (2)−0.005 (3)0.002 (2)
C150.059 (3)0.045 (3)0.059 (4)0.019 (2)0.013 (3)−0.002 (2)
C160.037 (2)0.046 (3)0.038 (3)0.0091 (19)0.0081 (19)0.007 (2)
C170.0269 (18)0.0267 (19)0.034 (3)0.0001 (14)0.0028 (16)0.0013 (18)
C180.064 (3)0.029 (2)0.044 (3)0.001 (2)0.006 (2)0.002 (2)
C190.043 (2)0.030 (2)0.057 (3)−0.0062 (18)0.013 (2)−0.010 (2)
C200.058 (3)0.030 (2)0.066 (4)0.001 (2)0.005 (2)−0.002 (2)
C210.059 (3)0.036 (3)0.096 (5)0.004 (2)0.010 (3)−0.002 (3)
C220.065 (3)0.030 (3)0.101 (5)−0.002 (2)0.032 (3)−0.016 (3)
C230.076 (4)0.041 (3)0.068 (4)−0.004 (3)0.025 (3)−0.014 (3)
C240.054 (3)0.034 (2)0.062 (4)−0.005 (2)0.016 (2)−0.004 (2)
Cl10.0447 (6)0.0503 (7)0.1041 (12)0.0008 (5)0.0424 (7)0.0047 (7)
Cl20.0892 (12)0.0357 (8)0.184 (2)0.0034 (7)0.0217 (12)−0.0074 (10)
Cl30.0502 (7)0.0626 (8)0.1090 (13)0.0091 (6)0.0447 (8)0.0078 (8)
Cl40.1212 (15)0.0392 (8)0.1399 (19)0.0014 (9)−0.0025 (13)−0.0050 (9)
Cl50.0964 (11)0.0528 (8)0.0534 (9)0.0074 (7)0.0063 (7)−0.0100 (7)
Cl60.1208 (15)0.0460 (8)0.1457 (19)0.0169 (9)0.0498 (13)−0.0285 (10)
Nd10.02001 (11)0.02489 (12)0.01098 (13)−0.00004 (7)0.00042 (7)0.00037 (7)
O10.0294 (13)0.0506 (17)0.0148 (15)−0.0125 (12)−0.0001 (10)0.0018 (13)
O20.0164 (11)0.0347 (13)0.0280 (16)−0.0028 (10)0.0016 (10)−0.0024 (12)
O30.0204 (12)0.0331 (15)0.0389 (18)−0.0065 (10)0.0019 (11)0.0011 (13)
O40.0265 (9)0.0502 (12)0.0100 (10)0.0078 (8)0.0011 (7)−0.0052 (9)
O50.0265 (9)0.0502 (12)0.0100 (10)0.0078 (8)0.0011 (7)−0.0052 (9)
O60.0221 (12)0.0384 (15)0.0341 (17)0.0068 (11)0.0009 (11)−0.0033 (13)
O70.0439 (16)0.0305 (14)0.0259 (17)−0.0006 (12)0.0047 (12)0.0042 (12)
O80.0422 (15)0.0278 (14)0.0263 (16)0.0043 (11)0.0051 (12)−0.0006 (12)
O90.0546 (19)0.0334 (16)0.048 (2)0.0087 (14)0.0006 (15)−0.0100 (15)
O1W0.091 (3)0.0291 (17)0.035 (2)0.0007 (16)0.012 (2)−0.0003 (14)
Geometric parameters (Å, °) top
C1—O11.235 (5)C15—H150.9300
C1—O21.282 (4)C16—Cl31.727 (5)
C1—C21.514 (5)C17—O71.258 (5)
C2—O31.418 (4)C17—O81.266 (5)
C2—H2A0.9700C17—C181.501 (6)
C2—H2B0.9700C18—O91.416 (6)
C3—O31.364 (5)C18—H18A0.9700
C3—C41.378 (6)C18—H18B0.9700
C3—C81.394 (5)C19—O91.363 (5)
C4—C51.388 (7)C19—C241.384 (7)
C4—H40.9300C19—C201.386 (7)
C5—C61.361 (7)C20—C211.393 (7)
C5—H50.9300C20—H200.9300
C6—C71.377 (7)C21—C221.359 (9)
C6—Cl21.743 (5)C21—H210.9300
C7—C81.380 (6)C22—C231.376 (8)
C7—H70.9300C22—Cl61.738 (5)
C8—Cl11.724 (4)C23—C241.381 (7)
C9—O51.217 (5)C23—H230.9300
C9—O41.288 (4)C24—Cl51.743 (6)
C9—C101.524 (5)Nd1—O2i2.430 (3)
C10—O61.434 (4)Nd1—O4ii2.439 (3)
C10—H10A0.9700Nd1—O82.451 (3)
C10—H10B0.9700Nd1—O1W2.491 (3)
C11—O61.366 (5)Nd1—O12.492 (2)
C11—C121.379 (6)Nd1—O52.511 (2)
C11—C161.396 (6)Nd1—O72.519 (3)
C12—C131.376 (7)Nd1—O42.549 (3)
C12—H120.9300Nd1—O22.553 (3)
C13—C141.367 (8)O2—Nd1ii2.430 (3)
C13—H130.9300O4—Nd1i2.439 (3)
C14—C151.381 (8)O1W—H1W0.811 (19)
C14—Cl41.737 (5)O1W—H2W0.807 (19)
C15—C161.382 (7)
O1—C1—O2120.2 (3)C19—C20—H20119.8
O1—C1—C2120.8 (3)C21—C20—H20119.8
O2—C1—C2119.0 (3)C22—C21—C20119.7 (5)
O3—C2—C1112.1 (3)C22—C21—H21120.1
O3—C2—H2A109.2C20—C21—H21120.1
C1—C2—H2A109.2C21—C22—C23121.2 (5)
O3—C2—H2B109.2C21—C22—Cl6119.8 (5)
C1—C2—H2B109.2C23—C22—Cl6119.0 (5)
H2A—C2—H2B107.9C22—C23—C24118.8 (6)
O3—C3—C4125.4 (4)C22—C23—H23120.6
O3—C3—C8116.2 (3)C24—C23—H23120.6
C4—C3—C8118.4 (4)C23—C24—C19121.6 (5)
C3—C4—C5120.3 (4)C23—C24—Cl5118.5 (5)
C3—C4—H4119.9C19—C24—Cl5119.9 (4)
C5—C4—H4119.9O2i—Nd1—O4ii150.72 (10)
C6—C5—C4120.2 (4)O2i—Nd1—O8128.82 (9)
C6—C5—H5119.9O4ii—Nd1—O878.94 (9)
C4—C5—H5119.9O2i—Nd1—O1W76.03 (11)
C5—C6—C7121.1 (4)O4ii—Nd1—O1W74.69 (11)
C5—C6—Cl2120.5 (4)O8—Nd1—O1W148.70 (10)
C7—C6—Cl2118.4 (4)O2i—Nd1—O170.88 (9)
C6—C7—C8118.6 (4)O4ii—Nd1—O1116.28 (9)
C6—C7—H7120.7O8—Nd1—O173.80 (9)
C8—C7—H7120.7O1W—Nd1—O1103.20 (11)
C7—C8—C3121.4 (4)O2i—Nd1—O5116.76 (8)
C7—C8—Cl1119.0 (3)O4ii—Nd1—O571.11 (9)
C3—C8—Cl1119.6 (3)O8—Nd1—O582.21 (9)
O5—C9—O4121.6 (3)O1W—Nd1—O5104.47 (11)
O5—C9—C10122.0 (3)O1—Nd1—O5152.33 (10)
O4—C9—C10116.3 (3)O2i—Nd1—O785.27 (9)
O6—C10—C9111.8 (3)O4ii—Nd1—O7123.39 (9)
O6—C10—H10A109.3O8—Nd1—O752.82 (9)
C9—C10—H10A109.3O1W—Nd1—O7158.46 (10)
O6—C10—H10B109.3O1—Nd1—O780.13 (9)
C9—C10—H10B109.3O5—Nd1—O774.37 (9)
H10A—C10—H10B107.9O2i—Nd1—O466.17 (8)
O6—C11—C12125.6 (4)O4ii—Nd1—O4111.05 (9)
O6—C11—C16116.3 (4)O8—Nd1—O4120.11 (9)
C12—C11—C16118.1 (4)O1W—Nd1—O485.44 (10)
C13—C12—C11120.9 (4)O1—Nd1—O4132.52 (9)
C13—C12—H12119.5O5—Nd1—O451.21 (8)
C11—C12—H12119.5O7—Nd1—O477.18 (9)
C14—C13—C12120.3 (5)O2i—Nd1—O2109.66 (8)
C14—C13—H13119.8O4ii—Nd1—O265.98 (8)
C12—C13—H13119.8O8—Nd1—O272.55 (9)
C13—C14—C15120.4 (5)O1W—Nd1—O281.43 (10)
C13—C14—Cl4120.3 (5)O1—Nd1—O251.24 (8)
C15—C14—Cl4119.2 (4)O5—Nd1—O2133.31 (8)
C14—C15—C16119.0 (5)O7—Nd1—O2115.44 (9)
C14—C15—H15120.5O4—Nd1—O2166.86 (9)
C16—C15—H15120.5C1—O1—Nd196.3 (2)
C15—C16—C11121.3 (4)C1—O2—Nd1ii147.6 (2)
C15—C16—Cl3119.1 (4)C1—O2—Nd192.1 (2)
C11—C16—Cl3119.6 (3)Nd1ii—O2—Nd1113.70 (9)
O7—C17—O8122.3 (4)C3—O3—C2118.1 (3)
O7—C17—C18118.6 (4)C9—O4—Nd1i154.2 (2)
O8—C17—C18119.0 (4)C9—O4—Nd191.6 (2)
O9—C18—C17109.3 (4)Nd1i—O4—Nd1113.52 (10)
O9—C18—H18A109.8C9—O5—Nd195.3 (2)
C17—C18—H18A109.8C11—O6—C10117.8 (3)
O9—C18—H18B109.8C17—O7—Nd190.8 (2)
C17—C18—H18B109.8C17—O8—Nd193.8 (2)
H18A—C18—H18B108.3C19—O9—C18117.7 (4)
O9—C19—C24116.3 (4)Nd1—O1W—H1W124 (3)
O9—C19—C20125.6 (5)Nd1—O1W—H2W123 (3)
C24—C19—C20118.2 (4)H1W—O1W—H2W113 (3)
C19—C20—C21120.5 (5)
O1—C1—C2—O3−5.7 (5)O2i—Nd1—O2—Nd1ii155.20 (14)
O2—C1—C2—O3174.8 (3)O4ii—Nd1—O2—Nd1ii6.46 (9)
O3—C3—C4—C5−176.3 (5)O8—Nd1—O2—Nd1ii−78.96 (12)
C8—C3—C4—C52.1 (7)O1W—Nd1—O2—Nd1ii83.44 (13)
C3—C4—C5—C6−1.1 (9)O1—Nd1—O2—Nd1ii−161.91 (17)
C4—C5—C6—C7−0.5 (9)O5—Nd1—O2—Nd1ii−18.41 (18)
C4—C5—C6—Cl2177.4 (5)O7—Nd1—O2—Nd1ii−110.62 (11)
C5—C6—C7—C81.1 (9)O4—Nd1—O2—Nd1ii86.1 (3)
Cl2—C6—C7—C8−176.9 (4)C4—C3—O3—C27.8 (6)
C6—C7—C8—C30.0 (8)C8—C3—O3—C2−170.5 (3)
C6—C7—C8—Cl1178.8 (4)C1—C2—O3—C3−79.9 (4)
O3—C3—C8—C7176.9 (4)O5—C9—O4—Nd1i173.1 (4)
C4—C3—C8—C7−1.6 (7)C10—C9—O4—Nd1i−9.7 (7)
O3—C3—C8—Cl1−1.8 (5)O5—C9—O4—Nd15.1 (4)
C4—C3—C8—Cl1179.7 (3)C10—C9—O4—Nd1−177.7 (3)
O5—C9—C10—O6−12.6 (5)O2i—Nd1—O4—C9167.9 (2)
O4—C9—C10—O6170.1 (3)O4ii—Nd1—O4—C9−43.72 (17)
O6—C11—C12—C13−179.0 (4)O8—Nd1—O4—C945.5 (2)
C16—C11—C12—C130.3 (7)O1W—Nd1—O4—C9−115.4 (2)
C11—C12—C13—C14−1.0 (8)O1—Nd1—O4—C9140.9 (2)
C12—C13—C14—C151.3 (9)O5—Nd1—O4—C9−2.70 (19)
C12—C13—C14—Cl4179.7 (4)O7—Nd1—O4—C977.4 (2)
C13—C14—C15—C16−1.0 (8)O2—Nd1—O4—C9−118.1 (3)
Cl4—C14—C15—C16−179.4 (4)O2i—Nd1—O4—Nd1i−6.45 (9)
C14—C15—C16—C110.4 (8)O4ii—Nd1—O4—Nd1i141.95 (15)
C14—C15—C16—Cl3179.3 (4)O8—Nd1—O4—Nd1i−128.87 (11)
O6—C11—C16—C15179.3 (4)O1W—Nd1—O4—Nd1i70.29 (13)
C12—C11—C16—C150.0 (7)O1—Nd1—O4—Nd1i−33.46 (18)
O6—C11—C16—Cl30.5 (5)O5—Nd1—O4—Nd1i−177.03 (17)
C12—C11—C16—Cl3−178.9 (3)O7—Nd1—O4—Nd1i−96.91 (12)
O7—C17—C18—O9167.3 (3)O2—Nd1—O4—Nd1i67.6 (4)
O8—C17—C18—O9−16.3 (5)O4—C9—O5—Nd1−5.2 (4)
O9—C19—C20—C21−178.8 (4)C10—C9—O5—Nd1177.7 (3)
C24—C19—C20—C210.9 (7)O2i—Nd1—O5—C9−6.8 (2)
C19—C20—C21—C22−0.5 (8)O4ii—Nd1—O5—C9142.5 (2)
C20—C21—C22—C23−0.1 (8)O8—Nd1—O5—C9−136.6 (2)
C20—C21—C22—Cl6−179.2 (4)O1W—Nd1—O5—C974.6 (2)
C21—C22—C23—C240.3 (8)O1—Nd1—O5—C9−106.7 (3)
Cl6—C22—C23—C24179.3 (4)O7—Nd1—O5—C9−83.1 (2)
C22—C23—C24—C190.2 (8)O4—Nd1—O5—C92.9 (2)
C22—C23—C24—Cl5179.2 (4)O2—Nd1—O5—C9166.5 (2)
O9—C19—C24—C23178.9 (4)C12—C11—O6—C102.3 (6)
C20—C19—C24—C23−0.8 (7)C16—C11—O6—C10−177.0 (4)
O9—C19—C24—Cl50.0 (6)C9—C10—O6—C11−73.9 (4)
C20—C19—C24—Cl5−179.7 (4)O8—C17—O7—Nd1−4.8 (4)
O2—C1—O1—Nd1−3.9 (4)C18—C17—O7—Nd1171.5 (3)
C2—C1—O1—Nd1176.7 (3)O2i—Nd1—O7—C17151.1 (2)
O2i—Nd1—O1—C1139.4 (2)O4ii—Nd1—O7—C17−35.4 (2)
O4ii—Nd1—O1—C1−9.7 (3)O8—Nd1—O7—C172.6 (2)
O8—Nd1—O1—C1−78.2 (2)O1W—Nd1—O7—C17−179.3 (3)
O1W—Nd1—O1—C169.5 (2)O1—Nd1—O7—C1779.7 (2)
O5—Nd1—O1—C1−109.2 (3)O5—Nd1—O7—C17−89.4 (2)
O7—Nd1—O1—C1−132.2 (2)O4—Nd1—O7—C17−142.3 (2)
O4—Nd1—O1—C1165.5 (2)O2—Nd1—O7—C1741.6 (2)
O2—Nd1—O1—C12.1 (2)O7—C17—O8—Nd14.9 (4)
O1—C1—O2—Nd1ii147.7 (3)C18—C17—O8—Nd1−171.4 (3)
C2—C1—O2—Nd1ii−32.8 (6)O2i—Nd1—O8—C17−44.6 (2)
O1—C1—O2—Nd13.7 (4)O4ii—Nd1—O8—C17145.8 (2)
C2—C1—O2—Nd1−176.8 (3)O1W—Nd1—O8—C17178.8 (2)
O2i—Nd1—O2—C1−44.94 (17)O1—Nd1—O8—C17−92.4 (2)
O4ii—Nd1—O2—C1166.3 (2)O5—Nd1—O8—C1773.7 (2)
O8—Nd1—O2—C180.9 (2)O7—Nd1—O8—C17−2.6 (2)
O1W—Nd1—O2—C1−116.7 (2)O4—Nd1—O8—C1737.8 (2)
O1—Nd1—O2—C1−2.06 (19)O2—Nd1—O8—C17−146.1 (2)
O5—Nd1—O2—C1141.5 (2)C24—C19—O9—C18−177.9 (4)
O7—Nd1—O2—C149.2 (2)C20—C19—O9—C181.8 (6)
O4—Nd1—O2—C1−114.0 (4)C17—C18—O9—C19161.7 (4)
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x, −y+1/2, z−1/2.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1W—H1W···O8i0.81 (2)1.98 (3)2.702 (4)148 (4)
O1W—H2W···Cl5i0.81 (2)2.89 (4)3.422 (4)125 (4)
O1W—H2W···O7ii0.81 (2)2.66 (2)3.395 (5)152 (4)
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x, −y+1/2, z−1/2.
Table 1
Selected geometric parameters (Å, °) top
Nd1—O2i2.430 (3)Nd1—O52.511 (2)
Nd1—O4ii2.439 (3)Nd1—O72.519 (3)
Nd1—O82.451 (3)Nd1—O42.549 (3)
Nd1—O1W2.491 (3)Nd1—O22.553 (3)
Nd1—O12.492 (2)
O8—Nd1—O1W148.70 (10)O1W—Nd1—O485.44 (10)
O8—Nd1—O173.80 (9)O1—Nd1—O4132.52 (9)
O1W—Nd1—O1103.20 (11)O5—Nd1—O451.21 (8)
O8—Nd1—O582.21 (9)O7—Nd1—O477.18 (9)
O1W—Nd1—O5104.47 (11)O8—Nd1—O272.55 (9)
O1—Nd1—O5152.33 (10)O1W—Nd1—O281.43 (10)
O8—Nd1—O752.82 (9)O1—Nd1—O251.24 (8)
O1W—Nd1—O7158.46 (10)O5—Nd1—O2133.31 (8)
O1—Nd1—O780.13 (9)O7—Nd1—O2115.44 (9)
O5—Nd1—O774.37 (9)O4—Nd1—O2166.86 (9)
O8—Nd1—O4120.11 (9)C1—O1—Nd196.3 (2)
C1—C2—O3—C3−79.9 (4)C17—C18—O9—C19161.7 (4)
C9—C10—O6—C11−73.9 (4)
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x, −y+1/2, z−1/2.
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1W—H1W···O8i0.81 (2)1.98 (3)2.702 (4)148 (4)
O1W—H2W···Cl5i0.81 (2)2.89 (4)3.422 (4)125 (4)
O1W—H2W···O7ii0.81 (2)2.66 (2)3.395 (5)152 (4)
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x, −y+1/2, z−1/2.
Acknowledgements top

The authors acknowledge Guangdong Medical College for supporting this work.

references
References top

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