supplementary materials


Acta Cryst. (2008). E64, m1364-m1365    [ doi:10.1107/S1600536808031450 ]

catena-Poly[[[diaqualanthanum(III)]-tetrakis[[mu]-N-(4-acetamidophenylsulfonyl)glycinato]-[diaqualanthanum(III)]-bis[[mu]-N-(4-acetamidophenylsulfonyl)glycinato]] 4,4'-bipyridine disolvate tetradecahydrate]

J.-G. Wang and J.-H. Qin

Abstract top

In the title compound, {[La2(C10H11N2O5S)6(H2O)4]·2C10H8N2·14H2O}n, the LaIII ions are in a slightly distorted bicapped trigonal prismatic geometry, and are linked by six carboxylate groups in a syn-syn bidentate bridging fashion to form a one-dimensional inorganic-organic alternating linear chain. These polymeric chains generate microchannels extending along [100], and these cavities are occupied by discrete tetradecameric water clusters, which interact with their surroundings and finally furnish the three-dimensional supramolecular network via 15 O-H...O, one O-H...S, two O-H...N and six N-H...O classical hydrogen bonds. 4,4-Bipyridine acts as an inserting component and hydrogen-bond acceptor, and it is a nonplanar molecule with a dihedral angle of 33.12 (13)° between the pyridine rings. Owing to the numerous classical hydrogen bonds, the observed weak intermolecular C-H...O, C-H...[pi] and [pi]-[pi] stacking interactions can be neglected with regard to stabilizing the network.

Comment top

Organic carboxylates or N-donor ligands have been widely used in construction of coordination polymers containing transition metals. Meanwhile, in contrast to the well investigated transition metal system, the lanthanide coordination polymers have been less studied (Pan et al., 2003; Zhao et al., 2004; Guo et al., 2005). Whereas, lanthanide ions, with their high and variable coordination numbers, flexible coordination environments and luminescence properties, provide unique opportunities for discovery of unusual network topologies, biochemical sensors and fluoroimmunoassays (Hu et al., 2007; Zheng et al., 2004).

In the title compound, the asymmetric structure unit consists of one LaIII ion, three Np-acetamidobenzenesulfonyl-glycine acid(abglyH2) ligands, two coordinated water molecules, one uncoordinated 4,4-bipy molecule and seven lattice water molecules. The coordination geometry of the La ion shows a slightly distorted bicapped trigonal prism (Fig. 1). The alternation of two and four bridging abglyH- ligands between adjacent La centers gives one-dimensional inorganic-organic alternating linear chains (Fig. 2), which are further connected to generate a three-dimensional supramolecular structure, by O—H···O, O—H···N, and N—H···O hydrogen bonds (Table 1). 4,4-bipyridine acts as an inserting component that has a subtle effect on the structural characteristics by self-assembled control, not as an excellent rodlike bifunctional bridging ligand as in the other multidimensional mixed-ligand coordination systems, which may result from the nature of lanthanide ions having a strong affinity to oxygen atom. 4,4-bipyridine is a non-planar molecule and the dihedral angle is 33.12 (13)°.

Related literature top

For the structure of a related complex, see: Hu et al. (2007). For other related literature, see: Guo et al. (2005); Pan et al. (2003); Zhao et al. (2004); Zheng et al. (2004).

Experimental top

The mixture of La(NO3)3(0.2 mmol) and N-p-acetamidobenzenesulfonyl-glycine acid (abglyH2)(0.6 mmol), was stirred into 15 ml aqueous solution. Then the pH was adjusted to 5 or so with 1 M NaOH. And then 3 ml ethanol solution of 4, 4'-bipyridine (0.2 mmol) was added. The reaction mixture was heated on a water bath for 10 h at 343 K, and then filtered. Colorless crystals were produced after 20 days.

Refinement top

Water H atoms were located in a difference Fourier and allowed to ride in the range 0.80 - 0.91 Å with Uiso(H) = 1.5 Ueq(O). Other H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 Å (CH) and Uĩso~(H) = 1.2Ueq(C), with C—H = 0.97 Å (CH2) and Uĩso~(H) = 1.2Ueq(C), with C—H = 0.96 Å(CH3) and Uĩso~(H) = 1.5Ueq(C) and with N—H = 0.86 Å (NH) and Uĩso~(H) = 1.2Ueq(N).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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. A view of the title compound, H atoms, the 4,4'-bipyridine and the hydrate water molecules are omitted for clarity. The symmetry-related three ligands are unlabelled except for O10A, O21A, O16B. Symmetry code: A = 1 - x, 1 - y, -z, B = -x, 1 - y, -z.
[Figure 2] Fig. 2. A view of the chain structure of (I).
catena-Poly[[[diaqualanthanum(III)]-tetrakis[µ-N-(4- acetamidophenylsulfonyl)glycinato]-[diaqualanthanum(III)]-bis[µ-N- (4-acetamidophenylsulfonyl)glycinato]] 4,4'-bipyridine disolvate tetradecahydrate] top
Crystal data top
[La2(C10H11N2O5S)6(H2O)4]·2C10H8N2·14H2OZ = 1
Mr = 2542.08F(000) = 1304
Triclinic, P1Dx = 1.559 Mg m3
a = 9.6379 (8) ÅMo Kα radiation, λ = 0.71073 Å
b = 16.9589 (13) ÅCell parameters from 6389 reflections
c = 17.6005 (14) Åθ = 2.5–26.6°
α = 99.971 (1)°µ = 0.99 mm1
β = 105.758 (1)°T = 291 K
γ = 93.692 (1)°Block, colorless
V = 2707.9 (4) Å30.25 × 0.13 × 0.08 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
10013 independent reflections
Radiation source: fine-focus sealed tube8632 reflections with I > 2σ(I)
graphiteRint = 0.028
φ and ω scansθmax = 25.5°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
h = 1111
Tmin = 0.790, Tmax = 0.925k = 2020
20875 measured reflectionsl = 2121
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)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.072H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0313P)2 + 0.7554P]
where P = (Fo2 + 2Fc2)/3
10013 reflections(Δ/σ)max = 0.001
688 parametersΔρmax = 0.39 e Å3
0 restraintsΔρmin = 0.48 e Å3
Crystal data top
[La2(C10H11N2O5S)6(H2O)4]·2C10H8N2·14H2Oγ = 93.692 (1)°
Mr = 2542.08V = 2707.9 (4) Å3
Triclinic, P1Z = 1
a = 9.6379 (8) ÅMo Kα radiation
b = 16.9589 (13) ŵ = 0.99 mm1
c = 17.6005 (14) ÅT = 291 K
α = 99.971 (1)°0.25 × 0.13 × 0.08 mm
β = 105.758 (1)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
10013 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
8632 reflections with I > 2σ(I)
Tmin = 0.790, Tmax = 0.925Rint = 0.028
20875 measured reflectionsθmax = 25.5°
Refinement top
R[F2 > 2σ(F2)] = 0.032H-atom parameters constrained
wR(F2) = 0.072Δρmax = 0.39 e Å3
S = 1.02Δρmin = 0.48 e Å3
10013 reflectionsAbsolute structure: ?
688 parametersFlack parameter: ?
0 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
La10.258177 (16)0.499734 (10)0.006109 (9)0.02304 (6)
S10.89294 (8)0.61909 (5)0.34921 (5)0.03773 (19)
S20.40219 (7)0.42159 (4)0.29358 (4)0.02678 (16)
S30.79434 (8)0.25355 (4)0.15572 (5)0.03198 (17)
O10.1618 (2)0.63523 (12)0.02011 (13)0.0401 (5)
H1W0.19050.67660.00760.060*
H2W0.08320.63850.03040.060*
O20.1060 (2)0.35582 (12)0.05495 (13)0.0386 (5)
H3W0.12970.31810.03100.058*
H4W0.08890.34040.10410.058*
O30.9777 (3)0.89637 (17)0.55106 (19)0.0810 (9)
H5W1.03010.94140.57060.121*
H6W1.02770.85870.55980.121*
O40.0218 (3)0.72632 (16)0.20987 (16)0.0789 (9)
H7W0.06590.77230.21910.118*
H8W0.01590.71250.25160.118*
O50.2932 (4)0.6603 (2)0.24267 (18)0.1020 (11)
H9W0.21670.68080.22640.153*
H10W0.31960.63620.20490.153*
O60.4132 (3)0.64998 (15)0.39867 (17)0.0699 (8)
H11W0.35850.65460.35430.105*
H12W0.42970.60190.39660.105*
O70.6218 (3)0.78156 (17)0.4194 (2)0.0926 (10)
H13W0.69960.76180.42380.139*
H14W0.55150.74540.40520.139*
O80.6063 (3)0.91138 (16)0.34828 (18)0.0782 (9)
H15W0.54550.93640.36410.117*
H16W0.58980.86040.35570.117*
O90.9044 (4)0.9414 (2)0.3991 (2)0.1052 (11)
H17W0.81830.95020.38670.158*
H18W0.95130.90240.41120.158*
O100.6339 (2)0.56824 (14)0.10554 (12)0.0466 (6)
O110.4217 (2)0.57523 (12)0.13048 (12)0.0365 (5)
O121.0380 (2)0.61964 (15)0.34221 (14)0.0547 (7)
O130.8544 (3)0.68756 (14)0.39538 (14)0.0525 (6)
O140.8725 (3)0.23576 (15)0.42586 (15)0.0578 (7)
O150.1129 (2)0.48426 (12)0.08728 (11)0.0336 (5)
O160.07047 (19)0.50076 (12)0.14005 (11)0.0338 (5)
O170.53348 (19)0.41848 (12)0.27017 (12)0.0346 (5)
O180.3960 (2)0.48139 (12)0.36059 (12)0.0397 (5)
O190.4620 (3)0.04174 (16)0.3733 (2)0.0774 (9)
O200.3830 (2)0.39887 (12)0.06651 (12)0.0353 (5)
O210.6009 (2)0.39877 (14)0.04656 (14)0.0490 (6)
O220.9197 (2)0.28575 (13)0.22222 (13)0.0436 (5)
O230.8024 (2)0.24757 (13)0.07503 (13)0.0435 (5)
O240.5300 (4)0.14674 (17)0.0583 (2)0.0925 (11)
N10.1019 (4)0.1134 (2)0.2089 (2)0.0775 (11)
N20.1528 (3)0.22331 (19)0.0229 (2)0.0563 (8)
N30.7608 (3)0.33389 (16)0.48231 (15)0.0403 (6)
H30.70660.34250.51380.048*
N40.7902 (2)0.60788 (15)0.25785 (14)0.0345 (6)
H40.82140.57610.22500.041*
N50.2777 (3)0.11179 (16)0.39024 (17)0.0453 (7)
H50.20030.10900.40550.054*
N60.2788 (2)0.43271 (14)0.21596 (14)0.0299 (5)
H60.29680.42420.17020.036*
N70.6052 (3)0.07706 (17)0.18688 (19)0.0569 (8)
H70.61400.08190.23570.068*
N80.6694 (3)0.30760 (15)0.16910 (15)0.0364 (6)
H80.68710.34330.21270.044*
C10.0358 (4)0.0486 (3)0.2233 (2)0.0661 (11)
H10.02410.04930.25680.079*
C20.0498 (4)0.0198 (2)0.1921 (2)0.0566 (10)
H20.00040.06320.20480.068*
C30.1373 (4)0.0238 (2)0.1419 (2)0.0543 (9)
C40.2095 (5)0.0430 (3)0.1278 (3)0.0819 (15)
H4A0.27160.04340.09550.098*
C50.1892 (6)0.1087 (3)0.1616 (4)0.1008 (18)
H5A0.23910.15250.15100.121*
C60.1388 (4)0.2322 (2)0.0971 (2)0.0538 (9)
H6A0.13100.28370.12290.065*
C70.1351 (4)0.1704 (2)0.1382 (2)0.0491 (9)
H7A0.12460.18060.18980.059*
C80.1470 (4)0.0932 (2)0.1023 (2)0.0478 (9)
C90.1627 (5)0.0831 (2)0.0258 (3)0.0688 (12)
H90.17170.03220.00090.083*
C100.1652 (5)0.1486 (3)0.0111 (3)0.0710 (12)
H100.17620.13990.06270.085*
C110.7557 (5)0.2052 (2)0.5219 (2)0.0692 (12)
H11A0.68880.16070.48730.104*
H11B0.70940.23520.55750.104*
H11C0.83930.18530.55300.104*
C120.8020 (4)0.2592 (2)0.4717 (2)0.0442 (8)
C130.7945 (3)0.39958 (19)0.44881 (17)0.0342 (7)
C140.7545 (4)0.4732 (2)0.47753 (18)0.0436 (8)
H140.70730.47730.51740.052*
C150.7837 (4)0.5404 (2)0.44775 (18)0.0426 (8)
H150.75680.58970.46770.051*
C160.8528 (3)0.53434 (18)0.38848 (17)0.0326 (7)
C170.8907 (3)0.4608 (2)0.35814 (19)0.0414 (8)
H170.93500.45660.31710.050*
C180.8631 (3)0.3936 (2)0.38838 (19)0.0405 (8)
H180.89030.34440.36840.049*
C190.6322 (3)0.60124 (18)0.24138 (17)0.0315 (7)
H19A0.60440.65210.26400.038*
H19B0.60100.56000.26710.038*
C200.5574 (3)0.57995 (16)0.15174 (17)0.0278 (6)
C210.2910 (4)0.0189 (2)0.4262 (3)0.0635 (11)
H21A0.29540.07010.39410.095*
H21B0.19180.01270.42420.095*
H21C0.34670.01650.48100.095*
C220.3518 (4)0.0474 (2)0.3941 (2)0.0489 (9)
C230.3099 (3)0.18314 (18)0.36461 (19)0.0371 (7)
C240.2253 (3)0.24512 (19)0.3760 (2)0.0425 (8)
H240.15070.23790.39930.051*
C250.2512 (3)0.31701 (19)0.35326 (18)0.0382 (7)
H250.19440.35820.36130.046*
C260.3621 (3)0.32816 (17)0.31820 (16)0.0291 (6)
C270.4451 (3)0.26621 (19)0.30571 (19)0.0396 (8)
H270.51890.27340.28190.048*
C280.4193 (4)0.1935 (2)0.3285 (2)0.0448 (8)
H280.47490.15200.31950.054*
C290.1371 (3)0.45656 (18)0.21862 (17)0.0293 (6)
H29A0.15040.50040.26430.035*
H29B0.07940.41150.22670.035*
C300.0555 (3)0.48297 (16)0.14311 (16)0.0242 (6)
C310.5402 (6)0.2210 (2)0.1623 (3)0.0936 (16)
H31A0.47020.26060.12220.140*
H31B0.50820.20870.20960.140*
H31C0.63220.24180.17570.140*
C320.5558 (4)0.1454 (2)0.1296 (3)0.0618 (11)
C330.6435 (4)0.00059 (19)0.1758 (2)0.0422 (8)
C340.6969 (4)0.0612 (2)0.2442 (2)0.0486 (9)
H340.70120.04970.29450.058*
C350.7435 (4)0.1381 (2)0.2387 (2)0.0449 (8)
H350.77980.17790.28490.054*
C360.7356 (3)0.15532 (17)0.16363 (18)0.0328 (7)
C370.6801 (4)0.0964 (2)0.0957 (2)0.0467 (8)
H370.67380.10840.04540.056*
C380.6338 (4)0.0197 (2)0.1014 (2)0.0525 (9)
H380.59580.01960.05490.063*
C390.5270 (3)0.29862 (17)0.11036 (17)0.0307 (7)
H39A0.45260.29030.13680.037*
H39B0.51820.25130.06880.037*
C400.5024 (3)0.37176 (16)0.07175 (16)0.0266 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
La10.01933 (8)0.02993 (10)0.02388 (9)0.00613 (6)0.00830 (6)0.01146 (7)
S10.0345 (4)0.0441 (5)0.0298 (4)0.0070 (4)0.0029 (3)0.0090 (4)
S20.0236 (3)0.0294 (4)0.0283 (4)0.0054 (3)0.0055 (3)0.0106 (3)
S30.0291 (4)0.0326 (4)0.0405 (4)0.0096 (3)0.0136 (3)0.0156 (3)
O10.0328 (11)0.0365 (12)0.0628 (15)0.0106 (9)0.0250 (11)0.0203 (11)
O20.0398 (12)0.0346 (12)0.0428 (13)0.0061 (10)0.0122 (10)0.0104 (10)
O30.0721 (18)0.0707 (19)0.130 (3)0.0270 (15)0.0518 (19)0.0552 (19)
O40.115 (2)0.0629 (19)0.0624 (18)0.0146 (17)0.0333 (18)0.0175 (15)
O50.098 (2)0.146 (3)0.068 (2)0.041 (2)0.0359 (19)0.009 (2)
O60.091 (2)0.0465 (16)0.081 (2)0.0101 (14)0.0397 (17)0.0114 (14)
O70.098 (2)0.065 (2)0.126 (3)0.0141 (17)0.040 (2)0.0344 (19)
O80.099 (2)0.0625 (18)0.101 (2)0.0310 (16)0.0561 (19)0.0379 (17)
O90.096 (2)0.106 (3)0.133 (3)0.020 (2)0.043 (2)0.056 (2)
O100.0436 (13)0.0706 (17)0.0307 (12)0.0262 (12)0.0160 (10)0.0081 (11)
O110.0286 (11)0.0454 (13)0.0337 (12)0.0027 (9)0.0060 (9)0.0081 (10)
O120.0304 (12)0.0812 (19)0.0475 (14)0.0134 (12)0.0032 (11)0.0199 (13)
O130.0668 (16)0.0419 (14)0.0428 (14)0.0031 (12)0.0101 (12)0.0044 (11)
O140.0787 (18)0.0514 (16)0.0529 (16)0.0204 (14)0.0284 (14)0.0162 (13)
O150.0289 (10)0.0503 (13)0.0288 (11)0.0078 (9)0.0136 (9)0.0178 (10)
O160.0218 (10)0.0515 (13)0.0320 (11)0.0142 (9)0.0085 (9)0.0141 (10)
O170.0224 (10)0.0384 (12)0.0452 (12)0.0048 (9)0.0084 (9)0.0156 (10)
O180.0454 (13)0.0376 (13)0.0327 (12)0.0072 (10)0.0069 (10)0.0043 (10)
O190.082 (2)0.0539 (17)0.132 (3)0.0332 (15)0.062 (2)0.0535 (18)
O200.0316 (11)0.0431 (13)0.0377 (12)0.0163 (10)0.0119 (10)0.0173 (10)
O210.0377 (12)0.0573 (15)0.0640 (16)0.0024 (11)0.0208 (12)0.0350 (13)
O220.0305 (11)0.0435 (13)0.0537 (14)0.0036 (10)0.0049 (11)0.0132 (11)
O230.0518 (14)0.0434 (13)0.0476 (14)0.0143 (11)0.0262 (11)0.0197 (11)
O240.134 (3)0.0467 (18)0.070 (2)0.0152 (17)0.007 (2)0.0095 (16)
N10.080 (3)0.065 (2)0.100 (3)0.018 (2)0.031 (2)0.036 (2)
N20.0494 (18)0.049 (2)0.070 (2)0.0031 (15)0.0138 (17)0.0179 (17)
N30.0515 (16)0.0413 (16)0.0330 (15)0.0045 (13)0.0189 (13)0.0102 (12)
N40.0294 (13)0.0478 (16)0.0263 (13)0.0003 (12)0.0070 (11)0.0108 (12)
N50.0483 (16)0.0425 (17)0.0569 (18)0.0110 (13)0.0227 (14)0.0273 (14)
N60.0282 (12)0.0412 (15)0.0268 (13)0.0155 (11)0.0112 (11)0.0147 (11)
N70.076 (2)0.0382 (18)0.059 (2)0.0015 (16)0.0182 (17)0.0183 (15)
N80.0349 (14)0.0370 (15)0.0355 (14)0.0140 (12)0.0063 (12)0.0047 (12)
C10.067 (3)0.071 (3)0.066 (3)0.010 (2)0.023 (2)0.025 (2)
C20.059 (2)0.055 (2)0.059 (2)0.0136 (19)0.019 (2)0.0149 (19)
C30.053 (2)0.049 (2)0.068 (3)0.0160 (18)0.023 (2)0.0154 (19)
C40.090 (3)0.066 (3)0.126 (4)0.042 (3)0.067 (3)0.046 (3)
C50.108 (4)0.071 (3)0.166 (6)0.050 (3)0.078 (4)0.061 (4)
C60.048 (2)0.043 (2)0.066 (3)0.0040 (17)0.0122 (19)0.0064 (19)
C70.045 (2)0.050 (2)0.051 (2)0.0071 (17)0.0121 (17)0.0077 (18)
C80.045 (2)0.043 (2)0.057 (2)0.0082 (16)0.0160 (18)0.0119 (18)
C90.091 (3)0.048 (2)0.076 (3)0.013 (2)0.040 (3)0.009 (2)
C100.094 (3)0.062 (3)0.062 (3)0.000 (2)0.033 (2)0.010 (2)
C110.098 (3)0.050 (2)0.073 (3)0.005 (2)0.040 (3)0.023 (2)
C120.052 (2)0.040 (2)0.0368 (19)0.0004 (16)0.0081 (17)0.0077 (15)
C130.0336 (16)0.0413 (19)0.0251 (15)0.0006 (14)0.0034 (13)0.0088 (14)
C140.059 (2)0.049 (2)0.0317 (17)0.0097 (17)0.0246 (16)0.0124 (15)
C150.056 (2)0.042 (2)0.0336 (18)0.0098 (16)0.0166 (16)0.0080 (15)
C160.0313 (16)0.0404 (18)0.0241 (15)0.0005 (14)0.0040 (13)0.0085 (13)
C170.0400 (18)0.054 (2)0.0367 (18)0.0067 (16)0.0195 (15)0.0121 (16)
C180.0423 (18)0.043 (2)0.0413 (19)0.0145 (15)0.0167 (16)0.0116 (15)
C190.0300 (15)0.0376 (17)0.0289 (16)0.0028 (13)0.0102 (13)0.0100 (13)
C200.0350 (16)0.0223 (15)0.0267 (15)0.0062 (12)0.0088 (13)0.0056 (12)
C210.073 (3)0.048 (2)0.083 (3)0.012 (2)0.028 (2)0.039 (2)
C220.054 (2)0.043 (2)0.057 (2)0.0108 (18)0.0187 (19)0.0239 (17)
C230.0407 (18)0.0351 (18)0.0403 (18)0.0054 (14)0.0119 (15)0.0197 (15)
C240.0434 (18)0.045 (2)0.053 (2)0.0128 (16)0.0244 (17)0.0258 (17)
C250.0384 (17)0.0415 (19)0.0447 (19)0.0167 (15)0.0184 (15)0.0205 (15)
C260.0322 (15)0.0302 (16)0.0269 (15)0.0069 (13)0.0062 (13)0.0132 (13)
C270.0406 (18)0.0427 (19)0.048 (2)0.0134 (15)0.0233 (16)0.0213 (16)
C280.050 (2)0.0386 (19)0.059 (2)0.0211 (16)0.0268 (18)0.0228 (17)
C290.0225 (14)0.0414 (18)0.0305 (16)0.0090 (13)0.0114 (12)0.0163 (13)
C300.0197 (13)0.0260 (15)0.0277 (15)0.0002 (11)0.0071 (12)0.0075 (12)
C310.130 (4)0.036 (2)0.116 (4)0.001 (3)0.032 (4)0.027 (3)
C320.065 (3)0.037 (2)0.076 (3)0.0011 (19)0.006 (2)0.017 (2)
C330.0458 (19)0.0318 (18)0.052 (2)0.0057 (15)0.0139 (17)0.0165 (16)
C340.068 (2)0.042 (2)0.043 (2)0.0083 (18)0.0227 (18)0.0171 (17)
C350.063 (2)0.0364 (19)0.0403 (19)0.0087 (16)0.0196 (17)0.0120 (15)
C360.0364 (16)0.0282 (16)0.0378 (17)0.0121 (13)0.0118 (14)0.0126 (14)
C370.064 (2)0.039 (2)0.0360 (19)0.0074 (17)0.0098 (17)0.0128 (16)
C380.076 (3)0.036 (2)0.039 (2)0.0008 (18)0.0058 (18)0.0078 (16)
C390.0269 (15)0.0316 (17)0.0360 (17)0.0065 (13)0.0090 (13)0.0118 (13)
C400.0263 (15)0.0295 (16)0.0261 (15)0.0028 (12)0.0084 (12)0.0096 (12)
Geometric parameters (Å, °) top
La1—O10i2.433 (2)C1—C21.381 (5)
La1—O21i2.442 (2)C1—H10.9300
La1—O152.4662 (18)C2—C31.383 (5)
La1—O202.4887 (19)C2—H20.9300
La1—O12.549 (2)C3—C41.388 (5)
La1—O16ii2.5505 (18)C3—C81.479 (5)
La1—O112.553 (2)C4—C51.378 (6)
La1—O22.641 (2)C4—H4A0.9300
S1—O131.428 (2)C5—H5A0.9300
S1—O121.436 (2)C6—C71.377 (5)
S1—N41.615 (2)C6—H6A0.9300
S1—C161.764 (3)C7—C81.378 (5)
S2—O181.434 (2)C7—H7A0.9300
S2—O171.4345 (19)C8—C91.377 (5)
S2—N61.598 (2)C9—C101.383 (5)
S2—C261.760 (3)C9—H90.9300
S3—O231.430 (2)C10—H100.9300
S3—O221.433 (2)C11—C121.502 (5)
S3—N81.602 (2)C11—H11A0.9600
S3—C361.765 (3)C11—H11B0.9600
O1—H1W0.8232C11—H11C0.9600
O1—H2W0.8290C13—C141.383 (4)
O2—H3W0.8361C13—C181.390 (4)
O2—H4W0.8265C14—C151.379 (4)
O3—H5W0.8497C14—H140.9300
O3—H6W0.8351C15—C161.375 (4)
O4—H7W0.8315C15—H150.9300
O4—H8W0.8231C16—C171.381 (4)
O5—H9W0.8356C17—C181.379 (4)
O5—H10W0.8273C17—H170.9300
O6—H11W0.8353C18—H180.9300
O6—H12W0.8372C19—C201.513 (4)
O7—H13W0.8312C19—H19A0.9700
O7—H14W0.8362C19—H19B0.9700
O8—H15W0.8261C21—C221.498 (4)
O8—H16W0.9075C21—H21A0.9600
O9—H17W0.8282C21—H21B0.9600
O9—H18W0.8497C21—H21C0.9600
O10—C201.238 (3)C23—C281.388 (4)
O10—La1i2.433 (2)C23—C241.391 (4)
O11—C201.252 (3)C24—C251.376 (4)
O14—C121.221 (4)C24—H240.9300
O15—C301.254 (3)C25—C261.390 (4)
O16—C301.259 (3)C25—H250.9300
O16—La1ii2.5505 (18)C26—C271.385 (4)
O19—C221.217 (4)C27—C281.388 (4)
O20—C401.253 (3)C27—H270.9300
O21—C401.245 (3)C28—H280.9300
O21—La1i2.442 (2)C29—C301.506 (4)
O24—C321.207 (5)C29—H29A0.9700
N1—C11.327 (5)C29—H29B0.9700
N1—C51.343 (6)C31—C321.507 (5)
N2—C101.332 (5)C31—H31A0.9600
N2—C61.333 (5)C31—H31B0.9600
N3—C121.350 (4)C31—H31C0.9600
N3—C131.407 (4)C33—C381.382 (4)
N3—H30.8600C33—C341.392 (5)
N4—C191.463 (3)C34—C351.378 (4)
N4—H40.8505C34—H340.9300
N5—C221.345 (4)C35—C361.386 (4)
N5—C231.407 (4)C35—H350.9300
N5—H50.8600C36—C371.372 (4)
N6—C291.459 (3)C37—C381.377 (4)
N6—H60.8600C37—H370.9300
N7—C321.360 (5)C38—H380.9300
N7—C331.405 (4)C39—C401.516 (4)
N7—H70.8600C39—H39A0.9700
N8—C391.457 (3)C39—H39B0.9700
N8—H80.8600
O10i—La1—O21i71.49 (8)N2—C10—C9123.8 (4)
O10i—La1—O15146.41 (8)N2—C10—H10118.1
O21i—La1—O15141.98 (8)C9—C10—H10118.1
O10i—La1—O2079.17 (7)C12—C11—H11A109.5
O21i—La1—O20119.96 (7)C12—C11—H11B109.5
O15—La1—O2078.48 (6)H11A—C11—H11B109.5
O10i—La1—O1135.58 (7)C12—C11—H11C109.5
O21i—La1—O170.64 (7)H11A—C11—H11C109.5
O15—La1—O175.22 (6)H11B—C11—H11C109.5
O20—La1—O1141.13 (7)O14—C12—N3123.9 (3)
O10i—La1—O16ii76.46 (6)O14—C12—C11121.3 (3)
O21i—La1—O16ii84.20 (7)N3—C12—C11114.8 (3)
O15—La1—O16ii104.41 (6)C14—C13—C18119.3 (3)
O20—La1—O16ii137.39 (7)C14—C13—N3117.3 (3)
O1—La1—O16ii77.47 (7)C18—C13—N3123.5 (3)
O10i—La1—O11119.68 (7)C15—C14—C13120.8 (3)
O21i—La1—O1178.85 (7)C15—C14—H14119.6
O15—La1—O1176.15 (6)C13—C14—H14119.6
O20—La1—O1172.14 (7)C16—C15—C14119.8 (3)
O1—La1—O1174.11 (7)C16—C15—H15120.1
O16ii—La1—O11150.42 (7)C14—C15—H15120.1
O10i—La1—O276.66 (7)C15—C16—C17120.0 (3)
O21i—La1—O2143.98 (7)C15—C16—S1121.1 (2)
O15—La1—O271.94 (6)C17—C16—S1118.9 (2)
O20—La1—O268.44 (6)C18—C17—C16120.4 (3)
O1—La1—O2127.18 (6)C18—C17—H17119.8
O16ii—La1—O272.22 (6)C16—C17—H17119.8
O11—La1—O2133.04 (6)C17—C18—C13119.7 (3)
O13—S1—O12119.51 (15)C17—C18—H18120.1
O13—S1—N4107.25 (14)C13—C18—H18120.1
O12—S1—N4104.86 (13)N4—C19—C20111.1 (2)
O13—S1—C16107.34 (14)N4—C19—H19A109.4
O12—S1—C16108.83 (14)C20—C19—H19A109.4
N4—S1—C16108.67 (13)N4—C19—H19B109.4
O18—S2—O17119.95 (13)C20—C19—H19B109.4
O18—S2—N6108.07 (12)H19A—C19—H19B108.0
O17—S2—N6106.06 (12)O10—C20—O11125.3 (3)
O18—S2—C26105.53 (13)O10—C20—C19118.1 (2)
O17—S2—C26107.46 (12)O11—C20—C19116.6 (2)
N6—S2—C26109.53 (13)C22—C21—H21A109.5
O23—S3—O22119.92 (13)C22—C21—H21B109.5
O23—S3—N8109.74 (13)H21A—C21—H21B109.5
O22—S3—N8105.41 (13)C22—C21—H21C109.5
O23—S3—C36106.02 (14)H21A—C21—H21C109.5
O22—S3—C36108.98 (13)H21B—C21—H21C109.5
N8—S3—C36106.02 (13)O19—C22—N5123.4 (3)
La1—O1—H1W124.8O19—C22—C21120.7 (3)
La1—O1—H2W121.2N5—C22—C21115.9 (3)
H1W—O1—H2W112.0C28—C23—C24119.6 (3)
La1—O2—H3W121.2C28—C23—N5123.3 (3)
La1—O2—H4W111.1C24—C23—N5117.1 (3)
H3W—O2—H4W110.5C25—C24—C23120.5 (3)
H5W—O3—H6W110.0C25—C24—H24119.7
H7W—O4—H8W111.8C23—C24—H24119.7
H9W—O5—H10W111.9C24—C25—C26120.1 (3)
H11W—O6—H12W109.2C24—C25—H25120.0
H13W—O7—H14W110.9C26—C25—H25120.0
H15W—O8—H16W105.5C27—C26—C25119.5 (3)
H17W—O9—H18W137.0C27—C26—S2120.0 (2)
C20—O10—La1i160.8 (2)C25—C26—S2120.5 (2)
C20—O11—La1124.64 (18)C26—C27—C28120.6 (3)
C30—O15—La1171.01 (18)C26—C27—H27119.7
C30—O16—La1ii121.43 (17)C28—C27—H27119.7
C40—O20—La1133.60 (18)C23—C28—C27119.7 (3)
C40—O21—La1i156.3 (2)C23—C28—H28120.2
C1—N1—C5115.3 (4)C27—C28—H28120.2
C10—N2—C6115.4 (3)N6—C29—C30113.0 (2)
C12—N3—C13128.7 (3)N6—C29—H29A109.0
C12—N3—H3115.6C30—C29—H29A109.0
C13—N3—H3115.6N6—C29—H29B109.0
C19—N4—S1120.13 (19)C30—C29—H29B109.0
C19—N4—H4115.4H29A—C29—H29B107.8
S1—N4—H4111.8O15—C30—O16124.1 (2)
C22—N5—C23128.6 (3)O15—C30—C29119.7 (2)
C22—N5—H5115.7O16—C30—C29116.1 (2)
C23—N5—H5115.7C32—C31—H31A109.5
C29—N6—S2123.50 (18)C32—C31—H31B109.5
C29—N6—H6118.3H31A—C31—H31B109.5
S2—N6—H6118.3C32—C31—H31C109.5
C32—N7—C33127.8 (3)H31A—C31—H31C109.5
C32—N7—H7116.1H31B—C31—H31C109.5
C33—N7—H7116.1O24—C32—N7123.4 (4)
C39—N8—S3122.6 (2)O24—C32—C31122.0 (4)
C39—N8—H8118.7N7—C32—C31114.6 (4)
S3—N8—H8118.7C38—C33—C34118.4 (3)
N1—C1—C2124.5 (4)C38—C33—N7123.9 (3)
N1—C1—H1117.8C34—C33—N7117.7 (3)
C2—C1—H1117.8C35—C34—C33121.2 (3)
C1—C2—C3120.1 (4)C35—C34—H34119.4
C1—C2—H2120.0C33—C34—H34119.4
C3—C2—H2120.0C34—C35—C36119.3 (3)
C2—C3—C4116.0 (4)C34—C35—H35120.4
C2—C3—C8121.9 (3)C36—C35—H35120.4
C4—C3—C8122.0 (4)C37—C36—C35119.9 (3)
C5—C4—C3120.0 (4)C37—C36—S3120.3 (2)
C5—C4—H4A120.0C35—C36—S3119.8 (2)
C3—C4—H4A120.0C36—C37—C38120.7 (3)
N1—C5—C4124.1 (4)C36—C37—H37119.7
N1—C5—H5A117.9C38—C37—H37119.7
C4—C5—H5A117.9C37—C38—C33120.5 (3)
N2—C6—C7124.5 (3)C37—C38—H38119.8
N2—C6—H6A117.7C33—C38—H38119.8
C7—C6—H6A117.7N8—C39—C40112.1 (2)
C6—C7—C8119.6 (4)N8—C39—H39A109.2
C6—C7—H7A120.2C40—C39—H39A109.2
C8—C7—H7A120.2N8—C39—H39B109.2
C7—C8—C9116.7 (3)C40—C39—H39B109.2
C7—C8—C3122.0 (3)H39A—C39—H39B107.9
C9—C8—C3121.2 (3)O21—C40—O20125.6 (3)
C8—C9—C10120.0 (4)O21—C40—C39117.5 (2)
C8—C9—H9120.0O20—C40—C39116.9 (2)
C10—C9—H9120.0
O10i—La1—O11—C200.6 (2)C14—C13—C18—C170.2 (5)
O21i—La1—O11—C2061.6 (2)N3—C13—C18—C17179.2 (3)
O15—La1—O11—C20147.3 (2)S1—N4—C19—C20172.33 (19)
O20—La1—O11—C2065.1 (2)La1i—O10—C20—O1165.3 (7)
O1—La1—O11—C20134.4 (2)La1i—O10—C20—C19114.3 (5)
O16ii—La1—O11—C20117.9 (2)La1—O11—C20—O1019.9 (4)
O2—La1—O11—C2099.1 (2)La1—O11—C20—C19159.66 (18)
O10i—La1—O20—C4038.9 (2)N4—C19—C20—O102.6 (4)
O21i—La1—O20—C4022.2 (3)N4—C19—C20—O11177.8 (2)
O15—La1—O20—C40166.3 (3)C23—N5—C22—O191.3 (6)
O1—La1—O20—C40118.2 (2)C23—N5—C22—C21178.5 (3)
O16ii—La1—O20—C4094.8 (3)C22—N5—C23—C288.6 (5)
O11—La1—O20—C4087.3 (3)C22—N5—C23—C24172.1 (3)
O2—La1—O20—C40118.7 (3)C28—C23—C24—C251.3 (5)
O13—S1—N4—C1954.5 (3)N5—C23—C24—C25179.4 (3)
O12—S1—N4—C19177.4 (2)C23—C24—C25—C260.3 (5)
C16—S1—N4—C1961.2 (3)C24—C25—C26—C270.6 (5)
O18—S2—N6—C2935.9 (3)C24—C25—C26—S2176.7 (2)
O17—S2—N6—C29165.7 (2)O18—S2—C26—C27134.9 (2)
C26—S2—N6—C2978.6 (2)O17—S2—C26—C275.8 (3)
O23—S3—N8—C3944.2 (3)N6—S2—C26—C27108.9 (3)
O22—S3—N8—C39174.6 (2)O18—S2—C26—C2542.4 (3)
C36—S3—N8—C3969.9 (3)O17—S2—C26—C25171.5 (2)
C5—N1—C1—C21.2 (7)N6—S2—C26—C2573.7 (3)
N1—C1—C2—C30.1 (6)C25—C26—C27—C280.5 (5)
C1—C2—C3—C41.5 (6)S2—C26—C27—C28176.9 (3)
C1—C2—C3—C8175.3 (4)C24—C23—C28—C271.4 (5)
C2—C3—C4—C51.4 (7)N5—C23—C28—C27179.3 (3)
C8—C3—C4—C5175.4 (4)C26—C27—C28—C230.5 (5)
C1—N1—C5—C41.3 (8)S2—N6—C29—C30165.5 (2)
C3—C4—C5—N10.0 (9)La1ii—O16—C30—O1519.3 (4)
C10—N2—C6—C70.7 (5)La1ii—O16—C30—C29158.89 (18)
N2—C6—C7—C80.3 (5)N6—C29—C30—O151.5 (4)
C6—C7—C8—C90.2 (5)N6—C29—C30—O16176.8 (2)
C6—C7—C8—C3177.3 (3)C33—N7—C32—O244.5 (7)
C2—C3—C8—C733.0 (5)C33—N7—C32—C31173.5 (4)
C4—C3—C8—C7150.4 (4)C32—N7—C33—C381.1 (6)
C2—C3—C8—C9144.4 (4)C32—N7—C33—C34177.6 (4)
C4—C3—C8—C932.2 (6)C38—C33—C34—C352.0 (5)
C7—C8—C9—C100.3 (6)N7—C33—C34—C35176.8 (3)
C3—C8—C9—C10177.2 (4)C33—C34—C35—C360.7 (5)
C6—N2—C10—C90.6 (6)C34—C35—C36—C370.8 (5)
C8—C9—C10—N20.1 (7)C34—C35—C36—S3179.8 (3)
C13—N3—C12—O143.9 (5)O23—S3—C36—C3713.3 (3)
C13—N3—C12—C11175.4 (3)O22—S3—C36—C37143.7 (3)
C12—N3—C13—C14171.7 (3)N8—S3—C36—C37103.3 (3)
C12—N3—C13—C189.3 (5)O23—S3—C36—C35167.7 (2)
C18—C13—C14—C150.9 (5)O22—S3—C36—C3537.3 (3)
N3—C13—C14—C15180.0 (3)N8—S3—C36—C3575.7 (3)
C13—C14—C15—C160.4 (5)C35—C36—C37—C380.8 (5)
C14—C15—C16—C171.0 (5)S3—C36—C37—C38179.9 (3)
C14—C15—C16—S1179.7 (2)C36—C37—C38—C330.5 (6)
O13—S1—C16—C155.6 (3)C34—C33—C38—C371.9 (5)
O12—S1—C16—C15136.2 (3)N7—C33—C38—C37176.8 (3)
N4—S1—C16—C15110.1 (3)S3—N8—C39—C40112.7 (2)
O13—S1—C16—C17175.0 (2)La1i—O21—C40—O2025.1 (7)
O12—S1—C16—C1744.4 (3)La1i—O21—C40—C39156.4 (4)
N4—S1—C16—C1769.3 (3)La1—O20—C40—O219.6 (5)
C15—C16—C17—C181.7 (5)La1—O20—C40—C39168.93 (18)
S1—C16—C17—C18178.9 (2)N8—C39—C40—O2147.5 (4)
C16—C17—C18—C131.1 (5)N8—C39—C40—O20133.9 (3)
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x, −y+1, −z.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1W···O23i0.822.112.872 (3)153
O1—H2W···O2ii0.831.992.818 (3)179
O2—H3W···N20.842.002.827 (4)171
O2—H4W···O4ii0.831.982.744 (3)154
O3—H5W···O9iii0.851.982.801 (4)162
O3—H6W···O14iv0.841.942.772 (3)175
O4—H7W···N1v0.831.992.781 (4)158
O4—H8W···O12vi0.822.413.166 (3)154
O4—H8W···S1vi0.822.943.711 (3)156
O5—H9W···O40.842.042.865 (4)167
O5—H10W···O110.832.032.844 (4)168
O6—H11W···O50.841.912.716 (4)160
O6—H12W···O180.842.012.805 (3)158
O7—H13W···O130.832.122.914 (4)160
O7—H14W···O60.842.002.810 (4)165
O8—H15W···O19v0.832.002.722 (4)145
O8—H16W···O70.911.882.708 (4)151
O9—H17W···O80.832.002.751 (4)151
N3—H3···O6vii0.862.153.007 (4)171
N4—H4···O16viii0.852.303.151 (3)173
N5—H5···O3vii0.862.062.921 (4)177
N6—H6···O200.862.193.040 (3)169
N7—H7···O8ix0.862.022.878 (4)172
N8—H8···O170.862.332.974 (3)131
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x, −y+1, −z; (iii) −x+2, −y+2, −z+1; (iv) −x+2, −y+1, −z+1; (v) x, y+1, z; (vi) x−1, y, z; (vii) −x+1, −y+1, −z+1; (viii) x+1, y, z; (ix) x, y−1, z.
Table 1
Hydrogen-bond geometry (Å, °)
top
D—H···AD—HH···AD···AD—H···A
O1—H1W···O23i0.822.112.872 (3)153
O1—H2W···O2ii0.831.992.818 (3)179
O2—H3W···N20.842.002.827 (4)171
O2—H4W···O4ii0.831.982.744 (3)154
O3—H5W···O9iii0.851.982.801 (4)162
O3—H6W···O14iv0.841.942.772 (3)175
O4—H7W···N1v0.831.992.781 (4)158
O4—H8W···O12vi0.822.413.166 (3)154
O4—H8W···S1vi0.822.943.711 (3)156
O5—H9W···O40.842.042.865 (4)167
O5—H10W···O110.832.032.844 (4)168
O6—H11W···O50.841.912.716 (4)160
O6—H12W···O180.842.012.805 (3)158
O7—H13W···O130.832.122.914 (4)160
O7—H14W···O60.842.002.810 (4)165
O8—H15W···O19v0.832.002.722 (4)145
O8—H16W···O70.911.882.708 (4)151
O9—H17W···O80.832.002.751 (4)151
N3—H3···O6vii0.862.153.007 (4)171
N4—H4···O16viii0.852.303.151 (3)173
N5—H5···O3vii0.862.062.921 (4)177
N6—H6···O200.862.193.040 (3)169
N7—H7···O8ix0.862.022.878 (4)172
N8—H8···O170.862.332.974 (3)131
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x, −y+1, −z; (iii) −x+2, −y+2, −z+1; (iv) −x+2, −y+1, −z+1; (v) x, y+1, z; (vi) x−1, y, z; (vii) −x+1, −y+1, −z+1; (viii) x+1, y, z; (ix) x, y−1, z.
Acknowledgements top

The authors thank Luo Yang Normal University for supporting thise work.

references
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