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Acta Crystallogr Sect E Struct Rep Online. 2010 July 1; 66(Pt 7): m740–m741.
Published online 2010 June 5. doi:  10.1107/S1600536810020520
PMCID: PMC3006889

(4-Amino­benzene­sulfonato)­hepta­aqua­gadolinium(III) 4-amino­benzene­sulfonate nitrate 4,4′-bipyridyl tetra­solvate dihydrate

Abstract

In the title compound, [Gd(C6H6O3S)(H2O)7](C6H6O3S)(NO3)·4C10H8N2·2H2O, the GdIII ion is octa­coordinated by seven water mol­ecules and one O-bonded 4-amino­benzene­sulfonate anion in a square-anti­prismatic arrangement. In the crystal, the components are linked by N—H(...)O, O—H(...)N and O—H(...)O hydrogen bonds.

Related literature

For background to lanthanide coordination networks, see: Karthikeyan et al. (1989 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m740-scheme1.jpg

Experimental

Crystal data

  • [Gd(C6H6O3S)(H2O)7](C6H6O3S)(NO3)·4C10H8N2·2H2O
  • M r = 1350.50
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m740-efi1.jpg
  • a = 33.529 (2) Å
  • b = 23.3375 (10) Å
  • c = 15.2046 (10) Å
  • V = 11897.3 (12) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 1.26 mm−1
  • T = 296 K
  • 0.12 × 0.10 × 0.08 mm

Data collection

  • Bruker APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2001 [triangle]) T min = 0.863, T max = 0.906
  • 41191 measured reflections
  • 10477 independent reflections
  • 8881 reflections with I > 2σ(I)
  • R int = 0.045

Refinement

  • R[F 2 > 2σ(F 2)] = 0.036
  • wR(F 2) = 0.088
  • S = 1.00
  • 10477 reflections
  • 811 parameters
  • 27 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.35 e Å−3
  • Δρmin = −0.53 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 5009 Friedel pairs
  • Flack parameter: 0.002 (1)

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: SAINT-Plus (Bruker, 2001 [triangle]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

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

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810020520/hb5454sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810020520/hb5454Isup2.hkl

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

Acknowledgments

Financial support from the Inter­national Cooperation Program for Excellent Lectures of 2008 by Shandong Provincial Education Department is gratefully acknowledged.

supplementary crystallographic information

Comment

The design and synthesis of metal-organic compounds has attracted continuous research interest not only because of their appealing structural and topological novelties, but also due to their interesting optical, electronic, magnetic, and catalytic properties, as well as their potential medical applications (Karthikeyan et al., 1989). Here, we describe the synthesis and structural characterization of the title compound.

As shown in Figure 1, Gd(III) is octacoordinated by senven water molecules and one p-amino-benzenesulfonate anion. The Gd—O bond lengths are in the range of 2.370 (4)—2.439 (4) Å. In the molecule, one p-amino-benzenesulfonate, one nitrate, and two water molecules disassociate. N—H···O2, N—H···S, O—H···N, O—H···N, O—H···O hydrogen bonding between the cationic and anionic moieties and the uncoordinated water molecules leads to a consolidation of the structure (Fig. 2; Table 2).

Experimental

A mixture of 4-aminobenzene sulfonic acid (1 mmol 0.17 g), gadolinium(III) nitrate hexahydrate (0.5 mmol, 0.17 g), and 4,4-bipyridine (1 mmol, 0.14 g) in 10 ml distilled water was sealed in a 25 ml Teflon-lined stainless steel autoclave and was kept at 433 K for three days. Colourless blocks of (I) were obtained upon cooling. Anal. C52H62GdN11O18S2: C, 46.22; H, 4.59; N, 11.41. Found: C, 46.01; H, 4.48; N, 11.23%.

Refinement

All hydrogen atoms bound to aromatic carbon atoms were refined in calculated positions using a riding model with a C—H distance of 0.93 Å and Uiso = 1.2Ueq(C). The hydrogen atoms bound to N atoms were refined in calculated positions using a riding model with a N—H distance of 0.86 Å and Uiso = 1.2Ueq(C). Water molecules are refined by using the 'DFIX' command with the hydrogen atoms were separated with 1.38 Å, and the lengths of bond H—O were constrained with 0.82 Å with error 0.02 and Uiso = 1.5Ueq (O). The location of the water H atoms should be regarded as less certain that those of the other H atoms.

Figures

Fig. 1.
The building blocks of (I) with displacement ellipsoids drawn at the 30% probability level; H atoms are given as spheres of arbitrary radius.
Fig. 2.
The crystal packing of (I), displayed with N—H···O and O—H···O hydrogen bonds as dashed lines.

Crystal data

[Gd(C6H6O3S)(H2O)7](C6H6O3S)(NO3)·4C10H8N2·2H2OF(000) = 5528
Mr = 1350.50Dx = 1.508 Mg m3
Orthorhombic, Aba2Mo Kα radiation, λ = 0.71073 Å
Hall symbol: A 2 -2acCell parameters from 10477 reflections
a = 33.529 (2) Åθ = 2.4–25.0°
b = 23.3375 (10) ŵ = 1.26 mm1
c = 15.2046 (10) ÅT = 296 K
V = 11897.3 (12) Å3Block, colourless
Z = 80.12 × 0.10 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer10477 independent reflections
Radiation source: fine-focus sealed tube8881 reflections with I > 2σ(I)
graphiteRint = 0.045
phi and ω scansθmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2001)h = −39→39
Tmin = 0.863, Tmax = 0.906k = −27→25
41191 measured reflectionsl = −18→18

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.088w = 1/[σ2(Fo2) + (0.044P)2 + 12.9607P] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.001
10477 reflectionsΔρmax = 0.35 e Å3
811 parametersΔρmin = −0.53 e Å3
27 restraintsAbsolute structure: Flack (1983), 5009 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.002 (1)

Special details

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)

xyzUiso*/Ueq
C11.01881 (15)0.6735 (2)0.4126 (3)0.0317 (11)
C21.04516 (16)0.6502 (2)0.4716 (3)0.0373 (12)
H21.06130.61980.45450.045*
C31.04792 (18)0.6714 (3)0.5561 (4)0.0423 (14)
H31.06580.65490.59550.051*
C41.02425 (16)0.7174 (2)0.5830 (3)0.0366 (13)
C50.99778 (17)0.7407 (2)0.5226 (3)0.0391 (14)
H50.98180.77140.53910.047*
C60.99492 (16)0.7190 (2)0.4389 (4)0.0392 (13)
H60.97680.73500.39950.047*
C70.9597 (2)0.5837 (3)0.5639 (5)0.065 (2)
H70.96680.61490.52940.078*
C80.9629 (2)0.5891 (3)0.6540 (5)0.058 (2)
H80.97260.62300.67810.069*
C90.9520 (2)0.5445 (3)0.7085 (4)0.0402 (16)
C100.9388 (3)0.4959 (3)0.6658 (4)0.069 (2)
H100.93160.46380.69830.083*
C110.9361 (3)0.4947 (4)0.5753 (5)0.083 (3)
H110.92590.46180.54920.099*
C120.95518 (19)0.5476 (3)0.8045 (4)0.0364 (15)
C130.9811 (2)0.5832 (3)0.8464 (5)0.065 (2)
H130.99760.60720.81390.077*
C140.9829 (3)0.5837 (4)0.9365 (5)0.077 (3)
H141.00100.60840.96300.092*
C150.9355 (3)0.5184 (4)0.9479 (5)0.074 (3)
H150.91950.49500.98260.089*
C160.9307 (2)0.5152 (3)0.8572 (5)0.063 (2)
H160.91140.49150.83270.075*
C170.8646 (2)0.6318 (3)0.9382 (5)0.056 (2)
H170.85040.60590.97260.067*
C180.8591 (2)0.6306 (3)0.8485 (5)0.053 (2)
H180.84140.60420.82450.064*
C190.87929 (19)0.6675 (3)0.7936 (4)0.0357 (16)
C200.9046 (2)0.7060 (3)0.8358 (5)0.055 (2)
H200.91890.73290.80360.066*
C210.9079 (2)0.7037 (4)0.9264 (5)0.063 (2)
H210.92500.73000.95290.076*
C220.87594 (19)0.6666 (3)0.6959 (5)0.0395 (17)
C230.8567 (2)0.6225 (3)0.6532 (4)0.056 (2)
H230.84450.59330.68500.067*
C240.8556 (3)0.6222 (4)0.5622 (6)0.068 (2)
H240.84280.59180.53450.081*
C250.8918 (2)0.7093 (3)0.6430 (5)0.0504 (18)
H250.90440.74070.66850.060*
C260.8890 (2)0.7054 (3)0.5529 (5)0.058 (2)
H260.90000.73470.51910.070*
C270.7098 (2)0.7503 (4)0.9084 (5)0.077 (2)
H270.68250.75510.90030.092*
C280.7333 (2)0.7988 (3)0.9122 (5)0.066 (2)
H280.72200.83490.90620.079*
C290.77372 (19)0.7930 (3)0.9250 (4)0.0522 (16)
C300.7882 (2)0.7383 (3)0.9354 (5)0.069 (2)
H300.81530.73220.94540.083*
C310.7622 (2)0.6925 (3)0.9310 (6)0.083 (3)
H310.77250.65590.93960.099*
C320.80115 (18)0.8427 (3)0.9256 (4)0.0506 (15)
C330.7922 (2)0.8937 (3)0.9665 (5)0.072 (2)
H330.76830.89830.99690.087*
C340.8197 (3)0.9385 (3)0.9614 (6)0.078 (2)
H340.81350.97250.99030.094*
C350.8615 (2)0.8864 (3)0.8783 (5)0.0587 (18)
H350.88510.88360.84640.070*
C360.8371 (2)0.8394 (3)0.8811 (5)0.0566 (18)
H360.84460.80550.85340.068*
C370.7417 (2)0.7246 (3)0.1777 (6)0.071 (2)
H370.71480.71510.18140.086*
C380.7696 (2)0.6819 (3)0.1772 (6)0.081 (2)
H380.76090.64420.18050.097*
C390.8195 (2)0.7462 (4)0.1683 (5)0.072 (2)
H390.84660.75420.16540.087*
C400.79343 (19)0.7909 (3)0.1685 (5)0.0617 (18)
H400.80310.82820.16550.074*
C410.75276 (18)0.7816 (3)0.1729 (4)0.0501 (15)
C420.72368 (16)0.8286 (3)0.1737 (4)0.0444 (14)
C430.68574 (18)0.8222 (3)0.1372 (4)0.0564 (17)
H430.67840.78810.11010.068*
C440.6595 (2)0.8671 (4)0.1419 (5)0.063 (2)
H440.63440.86200.11700.075*
C450.73194 (17)0.8813 (3)0.2124 (4)0.0541 (17)
H450.75680.88810.23760.065*
C460.7029 (2)0.9237 (3)0.2131 (5)0.063 (2)
H460.70900.95870.23890.075*
C470.87083 (17)0.8856 (2)0.3376 (4)0.0432 (14)
C480.86031 (16)0.9022 (2)0.2554 (6)0.0486 (14)
H480.87210.88450.20720.058*
C490.83240 (17)0.9449 (3)0.2418 (7)0.0632 (16)
H490.82560.95520.18470.076*
C500.81468 (18)0.9721 (3)0.3113 (6)0.0602 (18)
C510.8256 (2)0.9552 (3)0.3948 (5)0.0631 (19)
H510.81400.97300.44320.076*
C520.8533 (2)0.9124 (3)0.4081 (4)0.0557 (17)
H520.86020.90160.46500.067*
Gd10.914673 (6)0.583155 (8)0.24786 (4)0.02827 (7)
N11.02869 (15)0.7404 (2)0.6662 (3)0.0519 (13)
H1A1.04610.72640.70170.062*
H1B1.01400.76870.68240.062*
N20.7594 (2)0.5425 (3)0.0739 (6)0.0738 (19)
N30.9470 (2)0.5368 (3)0.5235 (4)0.0637 (19)
N40.9609 (2)0.5518 (3)0.9875 (4)0.0626 (17)
N50.88924 (17)0.6679 (3)0.9780 (4)0.0525 (15)
N60.87160 (17)0.6623 (3)0.5119 (4)0.0558 (15)
N70.78776 (18)1.0158 (3)0.2970 (5)0.088 (2)
H7A0.78201.02620.24420.106*
H7B0.77671.03280.34090.106*
N80.80819 (19)0.6914 (3)0.1722 (5)0.0732 (17)
N90.66714 (17)0.9169 (2)0.1790 (4)0.0606 (14)
N100.8535 (2)0.9358 (3)0.9186 (5)0.0723 (17)
N110.72363 (19)0.6974 (3)0.9154 (5)0.0815 (19)
O10.97175 (11)0.64181 (16)0.2889 (3)0.0445 (9)
O21.03318 (10)0.68583 (14)0.2462 (4)0.0483 (8)
O31.03391 (12)0.59050 (16)0.3044 (3)0.0515 (10)
O50.88950 (15)0.77808 (18)0.3359 (4)0.0797 (16)
O60.93894 (13)0.84568 (19)0.2913 (3)0.0678 (13)
O140.7721 (3)0.5527 (4)0.0030 (7)0.185 (5)
O150.7793 (2)0.5406 (3)0.1387 (7)0.155 (4)
O160.7249 (2)0.5362 (4)0.0840 (6)0.143 (3)
O200.92070 (18)0.8376 (2)0.4442 (3)0.0874 (17)
O1W0.88775 (12)0.65990 (17)0.3333 (2)0.0464 (10)
O2W0.86855 (12)0.54534 (19)0.3511 (3)0.0533 (11)
O3W0.85363 (11)0.59444 (18)0.1683 (3)0.0483 (10)
O4W0.89860 (12)0.49138 (17)0.1797 (3)0.0485 (10)
O5W0.96918 (11)0.54819 (17)0.1606 (2)0.0418 (9)
O6W0.95002 (14)0.52250 (18)0.3461 (2)0.0468 (10)
O7W0.91889 (12)0.66144 (19)0.1469 (3)0.0490 (11)
O8W0.7948 (2)0.5832 (3)0.3771 (5)0.0923 (19)
O9W0.94198 (16)0.8969 (2)0.6030 (3)0.0660 (13)
S21.01437 (4)0.64533 (6)0.30545 (9)0.0351 (3)
S50.90793 (5)0.83258 (7)0.35428 (12)0.0509 (4)
H1W0.8955 (12)0.6538 (11)0.3835 (6)0.076*
H2W0.8968 (11)0.68906 (11)0.3108 (18)0.076*
H3W0.8467 (2)0.5584 (15)0.3374 (17)0.076*
H6W0.8437 (6)0.6238 (9)0.1882 (18)0.076*
H8W0.8762 (5)0.4857 (9)0.199 (2)0.076*
H9W0.9625 (6)0.5555 (17)0.1100 (2)0.076*
H10W0.9884 (2)0.5665 (14)0.178 (2)0.076*
H11W0.955 (2)0.4895 (9)0.331 (3)0.076*
H12W0.950 (2)0.527 (2)0.3995 (6)0.076*
H14W0.89570 (17)0.6682 (13)0.133 (2)0.076*
H16W0.789 (2)0.6161 (9)0.390 (4)0.076*
H17W0.937 (2)0.884 (2)0.5539 (16)0.076*
H18W0.943 (2)0.8730 (18)0.642 (3)0.076*
H15W0.793 (2)0.5599 (18)0.417 (3)0.06 (3)*
H5W0.8410 (5)0.5651 (7)0.179 (2)0.14 (4)*
H4W0.8703 (9)0.51038 (19)0.347 (2)0.22 (7)*
H7W0.9160 (8)0.4709 (4)0.201 (2)0.15 (5)*
H13W0.9299 (13)0.6871 (7)0.1746 (11)0.15 (5)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.031 (3)0.034 (3)0.030 (3)−0.004 (2)−0.001 (2)−0.001 (2)
C20.038 (3)0.038 (3)0.036 (3)0.010 (2)−0.001 (2)0.000 (2)
C30.044 (3)0.049 (4)0.034 (3)0.001 (3)−0.014 (3)0.003 (3)
C40.039 (3)0.038 (3)0.033 (3)−0.006 (3)0.003 (2)−0.004 (2)
C50.040 (3)0.036 (3)0.041 (4)0.006 (3)−0.001 (3)−0.009 (3)
C60.038 (3)0.038 (3)0.042 (3)0.005 (2)−0.005 (2)0.000 (3)
C70.062 (5)0.076 (6)0.057 (5)−0.003 (4)0.009 (4)0.022 (4)
C80.064 (5)0.069 (5)0.040 (4)−0.021 (4)−0.001 (4)−0.001 (4)
C90.041 (4)0.040 (4)0.039 (3)−0.002 (3)0.009 (3)0.005 (3)
C100.124 (7)0.049 (5)0.035 (4)−0.016 (4)0.002 (4)0.003 (3)
C110.142 (8)0.058 (5)0.049 (5)−0.013 (5)−0.007 (5)−0.005 (4)
C120.038 (3)0.045 (4)0.027 (3)0.005 (3)−0.001 (3)0.001 (3)
C130.063 (5)0.080 (6)0.051 (4)−0.030 (4)0.003 (4)−0.008 (4)
C140.072 (5)0.108 (7)0.050 (5)−0.028 (5)−0.012 (4)−0.021 (5)
C150.110 (7)0.078 (7)0.034 (5)−0.015 (5)0.009 (4)0.001 (4)
C160.075 (5)0.072 (5)0.041 (4)−0.029 (4)0.006 (4)−0.006 (4)
C170.070 (5)0.057 (5)0.041 (4)−0.012 (4)0.001 (3)0.017 (4)
C180.056 (4)0.047 (4)0.057 (5)−0.019 (4)−0.011 (4)0.001 (4)
C190.041 (4)0.038 (4)0.029 (3)−0.001 (3)−0.008 (3)0.006 (3)
C200.058 (4)0.067 (5)0.041 (4)−0.024 (4)0.000 (3)0.010 (3)
C210.070 (5)0.073 (5)0.047 (4)−0.027 (4)−0.018 (4)0.003 (4)
C220.036 (4)0.040 (4)0.042 (4)0.011 (3)−0.003 (3)0.001 (4)
C230.080 (5)0.060 (5)0.028 (4)−0.022 (4)−0.002 (3)−0.001 (3)
C240.081 (6)0.071 (6)0.051 (5)−0.028 (5)0.003 (4)−0.009 (4)
C250.066 (5)0.043 (4)0.042 (4)−0.010 (3)0.000 (3)0.004 (3)
C260.075 (5)0.055 (5)0.045 (4)0.002 (4)0.006 (4)0.011 (4)
C270.044 (4)0.108 (7)0.078 (5)−0.015 (5)−0.005 (4)0.012 (5)
C280.048 (4)0.067 (5)0.081 (5)0.006 (4)0.008 (4)0.019 (4)
C290.051 (4)0.048 (4)0.057 (4)0.003 (3)0.004 (3)0.004 (3)
C300.050 (4)0.054 (4)0.103 (6)−0.007 (3)−0.016 (4)0.012 (4)
C310.067 (5)0.057 (5)0.123 (8)−0.014 (4)−0.013 (5)0.013 (5)
C320.047 (4)0.047 (4)0.058 (4)0.000 (3)−0.001 (3)0.018 (3)
C330.080 (5)0.052 (4)0.085 (6)0.005 (4)0.028 (4)0.007 (4)
C340.106 (6)0.047 (4)0.081 (5)−0.002 (4)0.017 (5)−0.003 (4)
C350.051 (4)0.059 (5)0.066 (5)0.005 (4)−0.004 (3)0.013 (4)
C360.047 (4)0.047 (4)0.075 (5)0.004 (3)−0.012 (3)−0.002 (4)
C370.045 (4)0.060 (5)0.109 (6)0.004 (3)0.004 (4)−0.007 (4)
C380.068 (5)0.055 (5)0.119 (7)0.010 (4)−0.010 (5)−0.010 (5)
C390.042 (4)0.086 (6)0.089 (6)0.006 (4)−0.010 (4)−0.014 (5)
C400.046 (4)0.049 (4)0.090 (5)0.006 (3)−0.017 (4)−0.001 (4)
C410.046 (4)0.054 (4)0.050 (4)0.001 (3)−0.007 (3)−0.006 (3)
C420.039 (3)0.053 (4)0.041 (3)0.002 (3)−0.005 (3)0.003 (3)
C430.044 (4)0.065 (5)0.061 (4)0.007 (3)−0.006 (3)−0.008 (3)
C440.041 (4)0.078 (6)0.069 (5)0.008 (4)−0.008 (3)0.008 (4)
C450.041 (3)0.049 (4)0.073 (4)−0.005 (3)−0.002 (3)0.006 (3)
C460.058 (4)0.045 (4)0.084 (5)0.005 (3)0.001 (3)0.001 (3)
C470.047 (3)0.036 (3)0.047 (4)−0.008 (3)0.006 (3)0.000 (3)
C480.055 (3)0.046 (3)0.045 (3)−0.005 (2)−0.001 (4)0.003 (4)
C490.060 (3)0.057 (4)0.073 (4)−0.001 (3)−0.016 (5)−0.008 (5)
C500.040 (3)0.041 (4)0.099 (6)−0.007 (3)−0.002 (4)−0.012 (4)
C510.061 (4)0.058 (5)0.070 (5)−0.004 (4)0.017 (4)−0.009 (4)
C520.059 (4)0.058 (4)0.049 (4)−0.006 (3)0.012 (3)0.007 (3)
Gd10.03323 (11)0.02543 (11)0.02617 (10)−0.00137 (9)0.00040 (18)−0.00023 (17)
N10.067 (3)0.053 (3)0.036 (3)0.003 (3)−0.008 (2)−0.011 (2)
N20.064 (4)0.056 (4)0.101 (6)0.008 (3)−0.026 (4)−0.001 (4)
N30.093 (5)0.069 (5)0.028 (3)0.011 (4)0.002 (3)0.005 (3)
N40.069 (4)0.077 (5)0.042 (3)0.011 (3)−0.006 (3)−0.008 (3)
N50.056 (3)0.058 (4)0.043 (3)−0.007 (3)−0.009 (3)0.011 (3)
N60.063 (4)0.070 (4)0.035 (3)−0.005 (3)0.004 (3)−0.006 (3)
N70.078 (4)0.063 (4)0.124 (6)0.023 (4)−0.013 (4)−0.020 (4)
N80.065 (4)0.067 (4)0.087 (5)0.022 (3)−0.015 (3)−0.005 (4)
N90.059 (4)0.056 (4)0.067 (4)0.010 (3)0.003 (3)0.008 (3)
N100.081 (4)0.055 (4)0.081 (4)−0.014 (3)0.009 (4)0.010 (3)
N110.064 (4)0.076 (5)0.104 (5)−0.019 (4)−0.007 (4)0.011 (4)
O10.042 (2)0.044 (2)0.047 (2)−0.0058 (18)−0.0118 (17)−0.0100 (18)
O20.056 (2)0.052 (2)0.0373 (17)−0.0096 (16)0.003 (3)0.003 (3)
O30.063 (3)0.041 (2)0.051 (2)0.012 (2)0.000 (2)−0.0114 (19)
O50.081 (3)0.033 (3)0.125 (5)−0.003 (2)−0.007 (3)−0.002 (3)
O60.054 (3)0.068 (3)0.082 (3)0.004 (2)0.013 (2)−0.004 (3)
O140.277 (14)0.140 (7)0.136 (7)0.073 (7)0.105 (9)0.027 (7)
O150.138 (6)0.094 (5)0.232 (10)−0.034 (5)−0.109 (7)0.059 (6)
O160.073 (5)0.174 (8)0.181 (8)−0.017 (5)−0.017 (5)−0.019 (7)
O200.109 (5)0.089 (4)0.064 (3)0.024 (3)−0.029 (3)−0.009 (3)
O1W0.069 (3)0.039 (2)0.031 (2)−0.001 (2)0.010 (2)−0.0043 (17)
O2W0.053 (3)0.041 (3)0.066 (3)0.004 (2)0.020 (2)0.015 (2)
O3W0.039 (2)0.036 (2)0.070 (3)0.0021 (19)−0.010 (2)0.000 (2)
O4W0.040 (2)0.039 (2)0.066 (3)−0.002 (2)0.005 (2)−0.010 (2)
O5W0.038 (2)0.052 (3)0.036 (2)−0.0039 (19)−0.0014 (17)−0.0115 (19)
O6W0.066 (3)0.046 (3)0.028 (2)0.010 (2)−0.002 (2)0.0045 (18)
O7W0.055 (3)0.052 (3)0.040 (2)−0.012 (2)−0.017 (2)0.016 (2)
O8W0.078 (4)0.086 (5)0.113 (5)0.030 (4)0.004 (4)−0.014 (5)
O9W0.078 (3)0.069 (3)0.052 (3)0.009 (3)0.004 (3)0.004 (2)
S20.0392 (7)0.0337 (7)0.0324 (7)−0.0002 (6)−0.0037 (6)−0.0052 (6)
S50.0543 (9)0.0388 (9)0.0594 (10)−0.0008 (7)−0.0002 (8)−0.0030 (7)

Geometric parameters (Å, °)

C1—C21.371 (7)C35—H350.9300
C1—C61.389 (7)C36—H360.9300
C1—S21.763 (5)C37—C381.367 (9)
C2—C31.380 (8)C37—C411.384 (9)
C2—H20.9300C37—H370.9300
C3—C41.396 (8)C38—N81.314 (9)
C3—H30.9300C38—H380.9300
C4—N11.382 (7)C39—N81.335 (9)
C4—C51.388 (8)C39—C401.361 (9)
C5—C61.372 (8)C39—H390.9300
C5—H50.9300C40—C411.382 (9)
C6—H60.9300C40—H400.9300
C7—N31.324 (10)C41—C421.468 (8)
C7—C81.380 (11)C42—C431.396 (8)
C7—H70.9300C42—C451.391 (8)
C8—C91.380 (9)C43—C441.369 (9)
C8—H80.9300C43—H430.9300
C9—C101.380 (10)C44—N91.317 (9)
C9—C121.465 (8)C44—H440.9300
C10—C111.379 (10)C45—C461.389 (9)
C10—H100.9300C45—H450.9300
C11—N31.312 (10)C46—N91.316 (9)
C11—H110.9300C46—H460.9300
C12—C131.361 (9)C47—C481.355 (10)
C12—C161.373 (9)C47—C521.372 (8)
C13—C141.372 (11)C47—S51.773 (6)
C13—H130.9300C48—C491.382 (8)
C14—N41.302 (10)C48—H480.9300
C14—H140.9300C49—C501.369 (11)
C15—N41.302 (10)C49—H490.9300
C15—C161.391 (10)C50—N71.381 (8)
C15—H150.9300C50—C511.378 (10)
C16—H160.9300C51—C521.381 (10)
C17—N51.325 (9)C51—H510.9300
C17—C181.376 (10)C52—H520.9300
C17—H170.9300Gd1—O6W2.375 (4)
C18—C191.377 (9)Gd1—O2W2.373 (4)
C18—H180.9300Gd1—O1W2.389 (4)
C19—C201.392 (9)Gd1—O3W2.392 (4)
C19—C221.489 (6)Gd1—O7W2.391 (4)
C20—C211.383 (10)Gd1—O5W2.401 (4)
C20—H200.9300Gd1—O12.434 (4)
C21—N51.307 (9)Gd1—O4W2.440 (4)
C21—H210.9300N1—H1A0.8600
C22—C251.388 (9)N1—H1B0.8600
C22—C231.377 (9)N2—O161.176 (8)
C23—C241.384 (10)N2—O141.184 (10)
C23—H230.9300N2—O151.190 (9)
C24—N61.322 (10)N7—H7A0.8600
C24—H240.9300N7—H7B0.8600
C25—C261.376 (9)O1—S21.453 (4)
C25—H250.9300O2—S21.450 (4)
C26—N61.320 (9)O3—S21.438 (4)
C26—H260.9300O5—S51.441 (5)
C27—N111.322 (10)O6—S51.446 (5)
C27—C281.381 (10)O20—S51.437 (5)
C27—H270.9300O1W—H1W0.819 (17)
C28—C291.375 (9)O1W—H2W0.820 (19)
C28—H280.9300O2W—H3W0.820 (17)
C29—C301.376 (9)O2W—H4W0.820 (7)
C29—C321.481 (9)O3W—H6W0.82 (2)
C30—C311.380 (10)O3W—H5W0.821 (18)
C30—H300.9300O4W—H8W0.82 (2)
C31—N111.321 (9)O4W—H7W0.82 (2)
C31—H310.9300O5W—H9W0.819 (11)
C32—C361.385 (9)O5W—H10W0.82 (2)
C32—C331.377 (10)O6W—H11W0.82 (3)
C33—C341.395 (10)O6W—H12W0.819 (12)
C33—H330.9300O8W—H16W0.82 (3)
C34—N101.310 (10)O8W—H15W0.82 (4)
C34—H340.9300O9W—H17W0.82 (3)
C35—N101.335 (9)O9W—H18W0.82 (4)
C35—C361.369 (9)
C2—C1—C6119.1 (5)C39—C40—C41120.9 (7)
C2—C1—S2120.7 (4)C39—C40—H40119.5
C6—C1—S2120.2 (4)C41—C40—H40119.5
C1—C2—C3120.6 (5)C37—C41—C40114.7 (6)
C1—C2—H2119.7C37—C41—C42122.7 (6)
C3—C2—H2119.7C40—C41—C42122.6 (6)
C2—C3—C4120.7 (5)C43—C42—C45116.4 (6)
C2—C3—H3119.6C43—C42—C41121.5 (6)
C4—C3—H3119.6C45—C42—C41122.1 (5)
N1—C4—C3120.4 (5)C44—C43—C42118.8 (7)
N1—C4—C5121.5 (5)C44—C43—H43120.6
C3—C4—C5118.1 (5)C42—C43—H43120.6
C6—C5—C4120.9 (5)N9—C44—C43125.0 (7)
C6—C5—H5119.5N9—C44—H44117.5
C4—C5—H5119.5C43—C44—H44117.5
C5—C6—C1120.5 (5)C46—C45—C42119.6 (6)
C5—C6—H6119.7C46—C45—H45120.2
C1—C6—H6119.7C42—C45—H45120.2
N3—C7—C8124.3 (7)N9—C46—C45123.3 (7)
N3—C7—H7117.9N9—C46—H46118.3
C8—C7—H7117.9C45—C46—H46118.3
C7—C8—C9120.4 (7)C48—C47—C52118.6 (6)
C7—C8—H8119.8C48—C47—S5120.9 (5)
C9—C8—H8119.8C52—C47—S5120.4 (5)
C8—C9—C10115.0 (6)C47—C48—C49121.3 (8)
C8—C9—C12122.8 (7)C47—C48—H48119.3
C10—C9—C12122.2 (7)C49—C48—H48119.3
C11—C10—C9120.5 (7)C50—C49—C48120.9 (9)
C11—C10—H10119.8C50—C49—H49119.6
C9—C10—H10119.8C48—C49—H49119.6
N3—C11—C10124.4 (8)C49—C50—N7120.4 (8)
N3—C11—H11117.8C49—C50—C51117.6 (7)
C10—C11—H11117.8N7—C50—C51122.0 (7)
C13—C12—C16116.4 (6)C52—C51—C50121.3 (7)
C13—C12—C9122.8 (7)C52—C51—H51119.3
C16—C12—C9120.7 (7)C50—C51—H51119.3
C12—C13—C14120.0 (7)C51—C52—C47120.2 (6)
C12—C13—H13120.0C51—C52—H52119.9
C14—C13—H13120.0C47—C52—H52119.9
N4—C14—C13124.5 (7)O6W—Gd1—O2W71.80 (15)
N4—C14—H14117.8O6W—Gd1—O1W107.07 (14)
C13—C14—H14117.8O2W—Gd1—O1W70.93 (15)
N4—C15—C16124.5 (8)O6W—Gd1—O3W144.17 (16)
N4—C15—H15117.7O2W—Gd1—O3W79.51 (15)
C16—C15—H15117.7O1W—Gd1—O3W82.48 (14)
C12—C16—C15118.6 (7)O6W—Gd1—O7W146.10 (15)
C12—C16—H16120.7O2W—Gd1—O7W138.36 (14)
C15—C16—H16120.7O1W—Gd1—O7W78.38 (14)
N5—C17—C18123.2 (7)O3W—Gd1—O7W68.99 (14)
N5—C17—H17118.4O6W—Gd1—O5W76.42 (13)
C18—C17—H17118.4O2W—Gd1—O5W137.30 (14)
C17—C18—C19121.5 (7)O1W—Gd1—O5W147.41 (14)
C17—C18—H18119.2O3W—Gd1—O5W114.14 (14)
C19—C18—H18119.2O7W—Gd1—O5W81.94 (14)
C20—C19—C18115.0 (6)O6W—Gd1—O177.38 (15)
C20—C19—C22121.0 (7)O2W—Gd1—O1123.49 (14)
C18—C19—C22124.0 (7)O1W—Gd1—O174.70 (13)
C21—C20—C19118.9 (7)O3W—Gd1—O1137.76 (14)
C21—C20—H20120.5O7W—Gd1—O171.85 (14)
C19—C20—H20120.5O5W—Gd1—O174.60 (13)
N5—C21—C20125.7 (7)O6W—Gd1—O4W81.63 (15)
N5—C21—H21117.2O2W—Gd1—O4W79.08 (15)
C20—C21—H21117.1O1W—Gd1—O4W143.66 (14)
C25—C22—C23116.3 (7)O3W—Gd1—O4W72.10 (15)
C25—C22—C19122.6 (7)O7W—Gd1—O4W114.26 (15)
C23—C22—C19121.1 (7)O5W—Gd1—O4W68.59 (13)
C24—C23—C22119.1 (7)O1—Gd1—O4W140.92 (13)
C24—C23—H23120.4C4—N1—H1A120.0
C22—C23—H23120.4C4—N1—H1B120.0
N6—C24—C23124.4 (8)H1A—N1—H1B120.0
N6—C24—H24117.8O16—N2—O14119.8 (10)
C23—C24—H24117.8O16—N2—O15116.1 (10)
C22—C25—C26120.2 (7)O14—N2—O15124.0 (10)
C22—C25—H25119.9C7—N3—C11115.4 (7)
C26—C25—H25119.9C14—N4—C15115.8 (7)
N6—C26—C25123.4 (7)C21—N5—C17115.6 (6)
N6—C26—H26118.3C26—N6—C24116.5 (6)
C25—C26—H26118.3C50—N7—H7A120.0
N11—C27—C28124.1 (7)C50—N7—H7B120.0
N11—C27—H27118.0H7A—N7—H7B120.0
C28—C27—H27118.0C38—N8—C39116.3 (6)
C29—C28—C27119.2 (7)C38—N8—H14W158.5 (9)
C29—C28—H28120.4C39—N8—H14W83.6 (7)
C27—C28—H28120.4C46—N9—C44116.9 (6)
C30—C29—C28117.1 (6)C34—N10—C35116.3 (7)
C30—C29—C32120.5 (6)C27—N11—C31116.1 (7)
C28—C29—C32122.4 (6)S2—O1—Gd1148.1 (2)
C31—C30—C29119.3 (7)S2—O2—H13W77.1 (2)
C31—C30—H30120.4Gd1—O1W—H1W105 (2)
C29—C30—H30120.4Gd1—O1W—H2W104.8 (18)
N11—C31—C30124.1 (8)H1W—O1W—H2W115 (3)
N11—C31—H31118.0Gd1—O2W—H3W106.0 (19)
C30—C31—H31118.0Gd1—O2W—H4W106 (2)
C36—C32—C33117.4 (6)H3W—O2W—H4W115 (3)
C36—C32—C29119.6 (6)Gd1—O3W—H6W104.7 (17)
C33—C32—C29123.0 (6)Gd1—O3W—H5W104.4 (16)
C32—C33—C34118.5 (7)H6W—O3W—H5W115 (2)
C32—C33—H33120.7Gd1—O4W—H8W101.1 (17)
C34—C33—H33120.7Gd1—O4W—H7W100.8 (14)
N10—C34—C33124.4 (8)H8W—O4W—H7W115 (3)
N10—C34—H34117.8Gd1—O5W—H9W103.9 (17)
C33—C34—H34117.8Gd1—O5W—H10W104.1 (18)
N10—C35—C36124.0 (7)H9W—O5W—H10W114 (3)
N10—C35—H35118.0Gd1—O6W—H11W118 (4)
C36—C35—H35118.0Gd1—O6W—H12W122 (4)
C35—C36—C32119.4 (7)H11W—O6W—H12W114 (5)
C35—C36—H36120.3H16W—O8W—H15W116 (5)
C32—C36—H36120.3H17W—O9W—H18W115 (4)
C38—C37—C41121.1 (7)O3—S2—O2112.1 (2)
C38—C37—H37119.4O3—S2—O1113.3 (2)
C41—C37—H37119.4O2—S2—O1110.9 (2)
N8—C38—C37123.5 (7)O3—S2—C1107.7 (2)
N8—C38—H38118.3O2—S2—C1107.1 (3)
C37—C38—H38118.3O1—S2—C1105.3 (2)
N8—C39—C40123.5 (7)O20—S5—O6113.5 (3)
N8—C39—H39118.3O20—S5—O5112.6 (4)
C40—C39—H39118.3O6—S5—O5111.5 (3)
N8—C39—H14W71.8 (5)O20—S5—C47106.7 (3)
C40—C39—H14W162.6 (6)O6—S5—C47105.2 (3)
H39—C39—H14W47.3O5—S5—C47106.7 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1W—H1W···N60.82 (2)2.12 (2)2.770 (7)136 (3)
O1W—H2W···O50.82 (2)2.13 (1)2.759 (6)134 (3)
O2W—H3W···O8W0.82 (2)1.93 (1)2.657 (7)147 (2)
O3W—H6W···N80.82 (2)1.99 (1)2.728 (7)149 (2)
O4W—H8W···N9i0.82 (2)2.19 (2)2.807 (7)133 (1)
O5W—H9W···N4ii0.82 (1)1.86 (1)2.647 (7)159 (2)
O5W—H10W···O30.82 (2)2.51 (2)3.236 (6)148 (4)
O5W—H10W···O10.82 (2)2.50 (3)2.931 (5)114 (2)
O6W—H11W···O3iii0.82 (3)1.95 (3)2.765 (6)175 (5)
O6W—H12W···N30.82 (1)1.90 (1)2.719 (7)178 (8)
O7W—H13W···N1iv0.82 (3)2.19 (2)2.902 (7)145 (3)
O7W—H14W···N5ii0.82 (1)2.37 (4)2.758 (7)110 (3)
O7W—H14W···O3W0.82 (1)2.29 (1)2.709 (6)112 (3)
O8W—H16W···N11v0.82 (3)1.98 (3)2.798 (9)176 (6)
O9W—H17W···O200.82 (3)2.06 (4)2.873 (7)169 (6)
O9W—H18W···O2vi0.82 (4)2.24 (5)3.028 (7)161 (7)
N1—H1A···O6vi0.862.222.972 (7)146
N1—H1B···O2vi0.862.142.958 (6)159
N7—H7B···O14vii0.862.513.289 (12)151
N7—H7A···O15viii0.862.633.345 (12)141
N7—H7A···O16viii0.862.463.302 (13)167

Symmetry codes: (i) −x+3/2, y−1/2, z; (ii) x, y, z−1; (iii) −x+2, −y+1, z; (iv) −x+2, −y+3/2, z−1/2; (v) −x+3/2, y, z−1/2; (vi) −x+2, −y+3/2, z+1/2; (vii) x, y+1/2, z+1/2; (viii) −x+3/2, y+1/2, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5454).

References

  • Bruker (2001). SAINT-Plus and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (2004). APEX2 Bruker AXS Inc., Madison, Wisconsin, USA.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Karthikeyan, S., Ryan, R. R. & Paine, R. T. (1989). Inorg. Chem.28, 2783–2789.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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