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

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ISSN: 2056-9890

Aqua­[tris­­(2-{5-[(4-methyl­phenyl)diazen­yl]-2-oxido­benzyl­­idene­amino}­eth­yl)amine]­samarium(III) aceto­nitrile monosolvate

aFaculty of Chemistry, Bu-Ali Sina University, Hamedan, Iran, and bChemistry Department, Isalmic Azad University, Buinzahra Branch, Qazvin, Iran
*Correspondence e-mail: saleh@basu.ac.ir

(Received 13 December 2011; accepted 21 December 2011; online 7 January 2012)

In the title compound, [Sm(C48H45N10O3)(H2O)]·CH3CN, the SmIII ion is coordinated by the hepta­dentate tris­(2-{5-[(4-methyl­pheny)diazen­yl]-2-oxidobenzyl­idene­amino}­eth­yl)amine trianionic ligand and a water mol­ecule. The resulting SmN4O4 coordination polyhedron is a distorted square anti­prism. In the crystal, complex mol­ecules are linked by O—H⋯O hydrogen bonds.

Related literature

For related samarium complexes, see: Salehzadeh et al. (2005[Salehzadeh, S., Nouri, S. M., Keypour, H. & Bagherzadeh, M. (2005). Polyhedron, 24, 1478-1486.]); Kanesato et al. (2004[Kanesato, M., Mizukami, S., Houjou, H., Tokuhisa, H., Koyama, E. & Nagawa, Y. (2004). J. Alloys Compd, 347, 307-310.]). For azo compounds, see: Khandar & Nejati (2000[Khandar, A. A. & Nejati, K. (2000). Polyhedron, 19, 607-613.]). For the synthesis of the ligand, see: Salehzadeh et al. (2011[Salehzadeh, S., Mahdavian, M. & Khalaj, M. (2011). Acta Cryst. E67, o606.]).

[Scheme 1]

Experimental

Crystal data
  • [Sm(C48H45N10O3)(H2O)]·C2H3N

  • Mr = 1019.36

  • Monoclinic, P 21 /c

  • a = 19.9785 (5) Å

  • b = 20.4849 (4) Å

  • c = 11.4683 (8) Å

  • β = 95.3750 (14)°

  • V = 4672.9 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 1.31 mm−1

  • T = 150 K

  • 0.35 × 0.11 × 0.08 mm

Data collection
  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (SORTAV; Blessing, 1995[Blessing, R. H. (1995). Acta Cryst. A51, 33-38.]) Tmin = 0.727, Tmax = 0.907

  • 32101 measured reflections

  • 10613 independent reflections

  • 5694 reflections with I > 2σ(I)

  • Rint = 0.105

Refinement
  • R[F2 > 2σ(F2)] = 0.056

  • wR(F2) = 0.128

  • S = 1.02

  • 10613 reflections

  • 598 parameters

  • 2 restraints

  • H-atom parameters constrained

  • Δρmax = 2.91 e Å−3

  • Δρmin = −0.96 e Å−3

Table 1
Selected bond lengths (Å)

Sm1—O2 2.302 (4)
Sm1—O3 2.321 (4)
Sm1—O1 2.346 (3)
Sm1—O4 2.432 (3)
Sm1—N2 2.556 (4)
Sm1—N3 2.605 (5)
Sm1—N4 2.671 (5)
Sm1—N1 2.753 (5)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O4—H4OA⋯O1i 0.93 1.76 2.624 (5) 153
O4—H4OB⋯O3i 0.83 2.00 2.761 (5) 153
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: COLLECT (Nonius, 2002[Nonius (2002). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO-SMN; program(s) used to solve structure: SIR92 (Altomare et al., 1994[Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.]); program(s) used to refine structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

The wide spread application of azo compounds and their metal complexes have attracted the interest of many investigators. In this work the synthesis and X-ray crystal structure of the samarium complex containing azo Schiff base ligand was reported. In the resulting complex the central Sm atom is eight-coordinate. The average of Sm–Nimine bond lengths [2.61 (5)Å] is shorter than Sm–Ntert bond length [2.75 (5)Å], also the average of Sm–Ophenolic bond length [2.32 (4)Å] is shorter than Sm–OH2O bond length [2.43 (3)Å]. The angles N2–Sm–N4, N2–Sm–N3 and N3–Sm–N4 have values of 85.17 (14), 83.96 (14) and 130.23 (15)°, respectively.

Related literature top

For related samarium complexes, see: Salehzadeh et al. (2005); Kanesato et al. (2004). For azo compounds, see: Khandar et al. (2000). For the synthesis of the ligand, see: Salehzadeh et al. (2011).

Experimental top

Azo Schiff base ligand H3L1(tris({[5-(4-methylphenylazo)salicylidene]amino}ethyl)amine) was synthesized according to the literature procedure (Salehzadeh et al., 2011). Then to a solution of ligand H3L1 (1 mmol) in methanol:choloform (1:1.5) (40 ml) was added Sm(NO3)3.6H2O, (1 mmol) in methanol (10 ml). Then triethylamine (3 mmol) was added to the mixture and was refluxed for 24 h. The resulting precipitate was filtered, washed with diethyl ether, and dried in vacuum. Orange needles were obtained by slow evaporationfrom an acetonitrile solution at room temperature after 10 h.

Refinement top

All H atoms bonded to C atoms were positioned geometrically [C–H = 0.95 to 0.99 Å] and were refined using a riding-model approximation, with Uiso(H) = 1.2 Ueq (C) or 1.5 Ueq (Cmethyl) The H atoms bonded to O atoms were located in a difference Fourier map and then included in their 'as found' positions and refined as riding with Uiso(H) = 1.5 Ueq (O).

Computing details top

Data collection: COLLECT (Nonius, 2002); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A view of the structure of the title complex, with displacement ellipsoids drawn at the 50% probability level.
Aqua[tris(2-{5-[(4-methylphenyl)diazenyl]-2- oxidobenzylideneamino}ethyl)amine]samarium(III) acetonitrile monosolvate top
Crystal data top
[Sm(C48H45N10O3)(H2O)]·C2H3NF(000) = 2084
Mr = 1019.36Dx = 1.449 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 32101 reflections
a = 19.9785 (5) Åθ = 2.7–27.5°
b = 20.4849 (4) ŵ = 1.31 mm1
c = 11.4683 (8) ÅT = 150 K
β = 95.3750 (14)°Needle, orange
V = 4672.9 (4) Å30.35 × 0.11 × 0.08 mm
Z = 4
Data collection top
Nonius KappaCCD
diffractometer
10613 independent reflections
Radiation source: fine-focus sealed tube5694 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.105
Detector resolution: 9 pixels mm-1θmax = 27.5°, θmin = 2.7°
ϕ scans and ω scans with κ offsetsh = 2525
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
k = 2621
Tmin = 0.727, Tmax = 0.907l = 1414
32101 measured reflections
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)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0418P)2 + 3.712P]
where P = (Fo2 + 2Fc2)/3
10613 reflections(Δ/σ)max = 0.002
598 parametersΔρmax = 2.91 e Å3
2 restraintsΔρmin = 0.96 e Å3
Crystal data top
[Sm(C48H45N10O3)(H2O)]·C2H3NV = 4672.9 (4) Å3
Mr = 1019.36Z = 4
Monoclinic, P21/cMo Kα radiation
a = 19.9785 (5) ŵ = 1.31 mm1
b = 20.4849 (4) ÅT = 150 K
c = 11.4683 (8) Å0.35 × 0.11 × 0.08 mm
β = 95.3750 (14)°
Data collection top
Nonius KappaCCD
diffractometer
10613 independent reflections
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
5694 reflections with I > 2σ(I)
Tmin = 0.727, Tmax = 0.907Rint = 0.105
32101 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0562 restraints
wR(F2) = 0.128H-atom parameters constrained
S = 1.02Δρmax = 2.91 e Å3
10613 reflectionsΔρmin = 0.96 e Å3
598 parameters
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
Sm10.536045 (15)0.623474 (13)0.44296 (3)0.02530 (10)
O10.60176 (19)0.53292 (16)0.5056 (3)0.0277 (9)
O20.6177 (2)0.66748 (17)0.5748 (3)0.0327 (10)
O30.48049 (19)0.59716 (17)0.6055 (3)0.0303 (9)
O40.47508 (18)0.52949 (16)0.3581 (3)0.0277 (9)
H4OA0.43860.51770.39850.042*
H4OB0.49930.49670.35990.042*
N10.4901 (2)0.6597 (2)0.2184 (4)0.0281 (11)
N20.5619 (2)0.7406 (2)0.3845 (4)0.0289 (11)
N30.6185 (2)0.5925 (2)0.2888 (4)0.0302 (12)
N40.4074 (2)0.6606 (2)0.4136 (4)0.0279 (11)
N50.8661 (2)0.4506 (2)0.4962 (5)0.0354 (13)
N60.8946 (2)0.4311 (2)0.5927 (4)0.0342 (12)
N70.8549 (3)0.8034 (2)0.5355 (5)0.0382 (13)
N80.8538 (3)0.8422 (3)0.4506 (5)0.0455 (14)
N90.2698 (3)0.6663 (2)0.8586 (5)0.0358 (13)
N100.2712 (2)0.6490 (2)0.9652 (5)0.0345 (12)
C10.5013 (3)0.7298 (3)0.1921 (5)0.0338 (15)
H1A0.46190.74660.14220.041*
H1B0.54110.73370.14740.041*
C20.5120 (3)0.7715 (3)0.3021 (5)0.0377 (16)
H2A0.52760.81550.28170.045*
H2B0.46910.77610.33800.045*
C30.5274 (3)0.6194 (3)0.1397 (5)0.0328 (14)
H3A0.51770.63520.05830.039*
H3B0.51170.57360.14270.039*
C40.6018 (3)0.6214 (3)0.1721 (5)0.0387 (15)
H4A0.62500.59690.11330.046*
H4B0.61760.66720.17220.046*
C50.4181 (3)0.6437 (3)0.2033 (5)0.0326 (15)
H5A0.41250.59590.21080.039*
H5B0.39960.65660.12360.039*
C60.3791 (3)0.6777 (3)0.2921 (5)0.0342 (15)
H6A0.38140.72560.28080.041*
H6B0.33130.66440.28050.041*
C70.6715 (3)0.5564 (3)0.3002 (5)0.0328 (14)
H7A0.69450.55080.23200.039*
C80.7001 (3)0.5235 (3)0.4044 (5)0.0313 (14)
C90.7654 (3)0.4989 (3)0.4052 (5)0.0331 (15)
H9A0.78760.50150.33560.040*
C100.7990 (3)0.4709 (3)0.5041 (6)0.0337 (15)
C110.7647 (3)0.4655 (3)0.6047 (5)0.0359 (15)
H11A0.78690.44670.67350.043*
C120.7002 (3)0.4866 (3)0.6057 (5)0.0360 (15)
H12A0.67830.48190.67520.043*
C130.6645 (3)0.5159 (3)0.5048 (5)0.0301 (14)
C140.9629 (3)0.4108 (3)0.5910 (5)0.0310 (15)
C151.0002 (3)0.4126 (3)0.4959 (6)0.0389 (16)
H15A0.98020.42760.42230.047*
C161.0671 (3)0.3925 (3)0.5074 (6)0.0457 (17)
H16A1.09240.39420.44150.055*
C171.0973 (3)0.3700 (3)0.6141 (6)0.0361 (15)
C181.0590 (3)0.3679 (3)0.7083 (6)0.0412 (16)
H18A1.07860.35240.78180.049*
C190.9926 (3)0.3881 (3)0.6976 (6)0.0436 (17)
H19A0.96720.38640.76350.052*
C201.1696 (3)0.3481 (3)0.6284 (6)0.0492 (19)
H20A1.19290.36460.56300.074*
H20B1.17140.30030.62940.074*
H20C1.19150.36520.70230.074*
C210.6170 (3)0.7718 (3)0.4055 (5)0.0316 (14)
H21A0.62100.81170.36460.038*
C220.6739 (3)0.7526 (3)0.4846 (5)0.0296 (14)
C230.7329 (3)0.7882 (3)0.4776 (5)0.0330 (15)
H23A0.73310.82290.42270.040*
C240.7910 (3)0.7745 (3)0.5477 (5)0.0360 (16)
C250.7889 (3)0.7256 (3)0.6328 (6)0.0425 (17)
H25A0.82800.71630.68370.051*
C260.7309 (3)0.6910 (3)0.6435 (5)0.0369 (16)
H26A0.73060.65900.70330.044*
C270.6719 (3)0.7014 (3)0.5689 (5)0.0315 (14)
C280.9173 (3)0.8707 (3)0.4305 (5)0.0380 (15)
C290.9156 (4)0.9195 (3)0.3476 (6)0.0535 (19)
H29A0.87390.93250.30790.064*
C300.9742 (4)0.9497 (3)0.3219 (6)0.055 (2)
H30A0.97230.98280.26370.066*
C311.0354 (3)0.9327 (3)0.3795 (6)0.0427 (17)
C321.0367 (3)0.8825 (3)0.4607 (6)0.0422 (16)
H32A1.07860.86900.49930.051*
C330.9785 (3)0.8517 (3)0.4868 (6)0.0407 (16)
H33A0.98040.81770.54330.049*
C341.1002 (3)0.9653 (3)0.3524 (7)0.061 (2)
H34A1.09770.97620.26890.091*
H34B1.13800.93550.37200.091*
H34C1.10691.00530.39890.091*
C350.3633 (3)0.6618 (2)0.4880 (5)0.0268 (14)
H35A0.31970.67650.45950.032*
C360.3723 (3)0.6432 (3)0.6117 (5)0.0291 (14)
C370.3202 (3)0.6589 (3)0.6804 (5)0.0313 (14)
H37A0.28270.68300.64610.038*
C380.3215 (3)0.6406 (3)0.7962 (5)0.0330 (15)
C390.3762 (3)0.6022 (3)0.8448 (5)0.0312 (14)
H39A0.37700.58730.92340.037*
C400.4274 (3)0.5865 (2)0.7797 (5)0.0265 (13)
H40A0.46350.56010.81260.032*
C410.4271 (3)0.6092 (2)0.6628 (5)0.0302 (14)
C420.2206 (3)0.6816 (3)1.0250 (5)0.0303 (14)
C430.1884 (3)0.7385 (3)0.9839 (5)0.0336 (15)
H43A0.19860.75760.91210.040*
C440.1414 (3)0.7670 (3)1.0491 (6)0.0382 (16)
H44A0.11870.80521.02010.046*
C450.1265 (3)0.7413 (3)1.1555 (5)0.0373 (16)
C460.1601 (3)0.6850 (3)1.1949 (5)0.0343 (15)
H46A0.15030.66601.26680.041*
C470.2075 (3)0.6564 (3)1.1316 (5)0.0313 (14)
H47A0.23130.61901.16180.038*
C480.0761 (3)0.7749 (3)1.2262 (6)0.0497 (18)
H48A0.06180.74471.28530.075*
H48B0.03680.78831.17390.075*
H48C0.09690.81351.26500.075*
N1S0.6088 (5)0.5337 (4)0.9036 (8)0.100 (3)
C1S0.6652 (6)0.5289 (4)0.9230 (9)0.076 (3)
C2S0.7374 (5)0.5226 (4)0.9526 (9)0.088 (3)
H2S10.75230.55511.01220.132*
H2S20.76080.52980.88240.132*
H2S30.74760.47870.98320.132*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sm10.02771 (17)0.02548 (16)0.02267 (17)0.00037 (14)0.00209 (12)0.00194 (15)
O10.026 (2)0.026 (2)0.032 (3)0.0015 (16)0.0031 (19)0.0061 (17)
O20.034 (3)0.037 (2)0.027 (2)0.0067 (19)0.0024 (19)0.0014 (18)
O30.032 (2)0.033 (2)0.026 (2)0.0010 (17)0.0027 (18)0.0015 (17)
O40.030 (2)0.026 (2)0.027 (2)0.0019 (16)0.0020 (18)0.0005 (17)
N10.027 (3)0.033 (3)0.025 (3)0.004 (2)0.003 (2)0.004 (2)
N20.030 (3)0.028 (3)0.028 (3)0.002 (2)0.001 (2)0.002 (2)
N30.033 (3)0.031 (3)0.025 (3)0.005 (2)0.000 (2)0.005 (2)
N40.033 (3)0.024 (3)0.026 (3)0.002 (2)0.001 (2)0.003 (2)
N50.028 (3)0.041 (3)0.036 (3)0.006 (2)0.000 (3)0.001 (2)
N60.030 (3)0.038 (3)0.034 (3)0.001 (2)0.001 (3)0.001 (2)
N70.036 (3)0.048 (3)0.029 (3)0.010 (2)0.005 (3)0.001 (3)
N80.041 (4)0.059 (4)0.037 (4)0.009 (3)0.002 (3)0.011 (3)
N90.041 (3)0.039 (3)0.028 (3)0.000 (2)0.007 (3)0.001 (2)
N100.035 (3)0.038 (3)0.031 (3)0.001 (2)0.003 (3)0.002 (2)
C10.030 (4)0.032 (3)0.038 (4)0.002 (3)0.005 (3)0.017 (3)
C20.039 (4)0.031 (3)0.042 (4)0.000 (3)0.002 (3)0.006 (3)
C30.040 (4)0.041 (3)0.017 (3)0.007 (3)0.001 (3)0.007 (3)
C40.041 (4)0.054 (4)0.022 (3)0.017 (3)0.008 (3)0.012 (3)
C50.035 (4)0.037 (3)0.025 (4)0.000 (3)0.000 (3)0.007 (3)
C60.024 (3)0.045 (4)0.033 (4)0.004 (3)0.002 (3)0.011 (3)
C70.030 (4)0.043 (4)0.027 (4)0.002 (3)0.008 (3)0.000 (3)
C80.029 (4)0.032 (3)0.032 (4)0.003 (3)0.001 (3)0.000 (3)
C90.045 (4)0.031 (3)0.023 (4)0.006 (3)0.008 (3)0.004 (3)
C100.030 (4)0.036 (3)0.036 (4)0.005 (3)0.005 (3)0.006 (3)
C110.036 (4)0.039 (4)0.031 (4)0.009 (3)0.006 (3)0.009 (3)
C120.036 (4)0.043 (4)0.030 (4)0.002 (3)0.004 (3)0.011 (3)
C130.033 (4)0.028 (3)0.029 (4)0.007 (3)0.000 (3)0.003 (3)
C140.029 (4)0.030 (3)0.035 (4)0.001 (3)0.006 (3)0.004 (3)
C150.036 (4)0.049 (4)0.031 (4)0.007 (3)0.002 (3)0.003 (3)
C160.042 (4)0.056 (4)0.039 (4)0.004 (3)0.007 (3)0.002 (3)
C170.027 (3)0.031 (3)0.049 (4)0.001 (3)0.002 (3)0.006 (3)
C180.031 (4)0.055 (4)0.036 (4)0.007 (3)0.004 (3)0.003 (3)
C190.037 (4)0.059 (4)0.035 (4)0.007 (3)0.003 (3)0.010 (3)
C200.035 (4)0.049 (4)0.063 (5)0.008 (3)0.002 (4)0.002 (4)
C210.038 (4)0.032 (3)0.025 (4)0.004 (3)0.003 (3)0.004 (3)
C220.024 (3)0.030 (3)0.035 (4)0.000 (2)0.002 (3)0.004 (3)
C230.035 (4)0.032 (3)0.033 (4)0.003 (3)0.005 (3)0.003 (3)
C240.040 (4)0.036 (4)0.031 (4)0.009 (3)0.005 (3)0.002 (3)
C250.042 (4)0.047 (4)0.037 (4)0.009 (3)0.003 (3)0.001 (3)
C260.044 (4)0.043 (4)0.023 (4)0.008 (3)0.002 (3)0.004 (3)
C270.036 (4)0.033 (3)0.025 (4)0.004 (3)0.004 (3)0.008 (3)
C280.035 (4)0.047 (4)0.032 (4)0.009 (3)0.000 (3)0.002 (3)
C290.043 (5)0.068 (5)0.048 (5)0.005 (4)0.003 (4)0.016 (4)
C300.049 (5)0.062 (5)0.054 (5)0.010 (4)0.002 (4)0.018 (4)
C310.041 (4)0.050 (4)0.038 (4)0.009 (3)0.012 (3)0.007 (3)
C320.025 (3)0.060 (4)0.043 (4)0.008 (3)0.005 (3)0.002 (4)
C330.042 (4)0.049 (4)0.031 (4)0.004 (3)0.003 (3)0.006 (3)
C340.044 (5)0.069 (5)0.071 (6)0.008 (4)0.013 (4)0.006 (4)
C350.028 (4)0.024 (3)0.027 (4)0.003 (2)0.003 (3)0.004 (3)
C360.027 (3)0.032 (3)0.030 (4)0.015 (2)0.012 (3)0.011 (3)
C370.027 (4)0.031 (3)0.036 (4)0.001 (3)0.000 (3)0.000 (3)
C380.030 (4)0.043 (4)0.027 (4)0.001 (3)0.008 (3)0.001 (3)
C390.033 (4)0.033 (3)0.027 (4)0.001 (3)0.004 (3)0.002 (3)
C400.025 (3)0.027 (3)0.028 (4)0.002 (2)0.005 (3)0.003 (3)
C410.045 (4)0.026 (3)0.019 (3)0.017 (3)0.001 (3)0.003 (2)
C420.029 (4)0.032 (3)0.030 (4)0.001 (3)0.001 (3)0.004 (3)
C430.042 (4)0.038 (4)0.021 (4)0.000 (3)0.008 (3)0.005 (3)
C440.039 (4)0.036 (4)0.039 (4)0.005 (3)0.003 (3)0.002 (3)
C450.036 (4)0.046 (4)0.029 (4)0.005 (3)0.000 (3)0.007 (3)
C460.036 (4)0.045 (4)0.023 (4)0.002 (3)0.006 (3)0.000 (3)
C470.032 (4)0.036 (3)0.025 (4)0.008 (3)0.001 (3)0.001 (3)
C480.055 (5)0.060 (4)0.035 (4)0.018 (4)0.010 (4)0.003 (3)
N1S0.117 (8)0.105 (6)0.075 (6)0.003 (6)0.008 (6)0.030 (5)
C1S0.115 (9)0.053 (5)0.062 (7)0.009 (6)0.015 (7)0.017 (4)
C2S0.090 (8)0.065 (6)0.112 (9)0.011 (5)0.025 (7)0.011 (5)
Geometric parameters (Å, º) top
Sm1—O22.302 (4)C17—C181.382 (9)
Sm1—O32.321 (4)C17—C201.507 (8)
Sm1—O12.346 (3)C18—C191.384 (8)
Sm1—O42.432 (3)C18—H18A0.9500
Sm1—N22.556 (4)C19—H19A0.9500
Sm1—N32.605 (5)C20—H20A0.9800
Sm1—N42.671 (5)C20—H20B0.9800
Sm1—N12.753 (5)C20—H20C0.9800
O1—C131.301 (6)C21—C221.440 (8)
O2—C271.293 (6)C21—H21A0.9500
O3—C411.326 (7)C22—C231.395 (7)
O4—H4OA0.9306C22—C271.430 (8)
O4—H4OB0.8259C23—C241.376 (8)
N1—C51.469 (7)C23—H23A0.9500
N1—C31.476 (7)C24—C251.402 (8)
N1—C11.488 (7)C25—C261.373 (8)
N2—C211.277 (7)C25—H25A0.9500
N2—C21.454 (7)C26—C271.406 (8)
N3—C71.288 (7)C26—H26A0.9500
N3—C41.473 (7)C28—C291.379 (8)
N4—C351.283 (7)C28—C331.384 (8)
N4—C61.495 (7)C29—C301.379 (9)
N5—N61.261 (6)C29—H29A0.9500
N5—C101.416 (7)C30—C311.380 (9)
N6—C141.429 (7)C30—H30A0.9500
N7—N81.255 (7)C31—C321.386 (8)
N7—C241.426 (7)C31—C341.514 (9)
N8—C281.435 (7)C32—C331.380 (8)
N9—N101.270 (6)C32—H32A0.9500
N9—C381.413 (7)C33—H33A0.9500
N10—C421.438 (7)C34—H34A0.9800
C1—C21.521 (8)C34—H34B0.9800
C1—H1A0.9900C34—H34C0.9800
C1—H1B0.9900C35—C361.463 (8)
C2—H2A0.9900C35—H35A0.9500
C2—H2B0.9900C36—C411.381 (8)
C3—C41.498 (8)C36—C371.401 (8)
C3—H3A0.9900C37—C381.377 (8)
C3—H3B0.9900C37—H37A0.9500
C4—H4A0.9900C38—C391.417 (8)
C4—H4B0.9900C39—C401.362 (8)
C5—C61.509 (8)C39—H39A0.9500
C5—H5A0.9900C40—C411.419 (8)
C5—H5B0.9900C40—H40A0.9500
C6—H6A0.9900C42—C471.375 (8)
C6—H6B0.9900C42—C431.393 (7)
C7—C81.443 (8)C43—C441.382 (8)
C7—H7A0.9500C43—H43A0.9500
C8—C91.397 (8)C44—C451.387 (8)
C8—C131.418 (8)C44—H44A0.9500
C9—C101.386 (8)C45—C461.388 (8)
C9—H9A0.9500C45—C481.517 (8)
C10—C111.400 (8)C46—C471.376 (8)
C11—C121.360 (8)C46—H46A0.9500
C11—H11A0.9500C47—H47A0.9500
C12—C131.433 (8)C48—H48A0.9800
C12—H12A0.9500C48—H48B0.9800
C14—C151.378 (8)C48—H48C0.9800
C14—C191.387 (8)N1S—C1S1.132 (11)
C15—C161.393 (8)C1S—C2S1.456 (12)
C15—H15A0.9500C2S—H2S10.9800
C16—C171.391 (9)C2S—H2S20.9800
C16—H16A0.9500C2S—H2S30.9800
O2—Sm1—O385.77 (14)C16—C15—H15A120.0
O2—Sm1—O176.50 (13)C17—C16—C15121.0 (6)
O3—Sm1—O182.33 (13)C17—C16—H16A119.5
O2—Sm1—O4150.50 (12)C15—C16—H16A119.5
O3—Sm1—O483.01 (13)C18—C17—C16118.1 (6)
O1—Sm1—O475.01 (12)C18—C17—C20120.1 (6)
O2—Sm1—N269.91 (14)C16—C17—C20121.8 (6)
O3—Sm1—N2123.51 (14)C17—C18—C19121.1 (6)
O1—Sm1—N2134.52 (14)C17—C18—H18A119.4
O4—Sm1—N2138.06 (13)C19—C18—H18A119.4
O2—Sm1—N394.97 (14)C18—C19—C14120.4 (6)
O3—Sm1—N3150.32 (13)C18—C19—H19A119.8
O1—Sm1—N369.11 (13)C14—C19—H19A119.8
O4—Sm1—N381.97 (13)C17—C20—H20A109.5
N2—Sm1—N383.96 (14)C17—C20—H20B109.5
O2—Sm1—N4125.88 (14)H20A—C20—H20B109.5
O3—Sm1—N468.93 (14)C17—C20—H20C109.5
O1—Sm1—N4140.16 (13)H20A—C20—H20C109.5
O4—Sm1—N474.62 (12)H20B—C20—H20C109.5
N2—Sm1—N485.17 (14)N2—C21—C22126.7 (5)
N3—Sm1—N4130.23 (15)N2—C21—H21A116.7
O2—Sm1—N1131.48 (13)C22—C21—H21A116.7
O3—Sm1—N1132.17 (13)C23—C22—C27119.9 (5)
O1—Sm1—N1128.85 (13)C23—C22—C21116.3 (5)
O4—Sm1—N174.26 (12)C27—C22—C21123.7 (5)
N2—Sm1—N163.88 (14)C24—C23—C22122.1 (6)
N3—Sm1—N166.91 (14)C24—C23—H23A118.9
N4—Sm1—N164.71 (14)C22—C23—H23A118.9
C13—O1—Sm1136.2 (3)C23—C24—C25118.2 (6)
C27—O2—Sm1136.1 (4)C23—C24—N7124.9 (6)
C41—O3—Sm1145.2 (3)C25—C24—N7116.7 (6)
Sm1—O4—H4OA113.0C26—C25—C24120.7 (6)
Sm1—O4—H4OB111.3C26—C25—H25A119.6
H4OA—O4—H4OB105.1C24—C25—H25A119.6
C5—N1—C3110.3 (4)C25—C26—C27122.3 (6)
C5—N1—C1110.8 (4)C25—C26—H26A118.9
C3—N1—C1108.8 (4)C27—C26—H26A118.9
C5—N1—Sm1106.7 (3)O2—C27—C26123.0 (5)
C3—N1—Sm1106.1 (3)O2—C27—C22120.5 (5)
C1—N1—Sm1114.0 (3)C26—C27—C22116.6 (5)
C21—N2—C2115.5 (5)C29—C28—C33119.2 (6)
C21—N2—Sm1127.8 (4)C29—C28—N8116.2 (6)
C2—N2—Sm1115.9 (3)C33—C28—N8124.5 (6)
C7—N3—C4115.9 (5)C28—C29—C30120.5 (7)
C7—N3—Sm1129.6 (4)C28—C29—H29A119.8
C4—N3—Sm1114.5 (3)C30—C29—H29A119.8
C35—N4—C6113.1 (5)C29—C30—C31121.1 (7)
C35—N4—Sm1129.3 (4)C29—C30—H30A119.5
C6—N4—Sm1117.4 (3)C31—C30—H30A119.5
N6—N5—C10112.9 (5)C30—C31—C32118.0 (6)
N5—N6—C14115.7 (5)C30—C31—C34121.8 (6)
N8—N7—C24112.8 (5)C32—C31—C34120.2 (6)
N7—N8—C28115.5 (5)C33—C32—C31121.5 (6)
N10—N9—C38115.6 (5)C33—C32—H32A119.3
N9—N10—C42112.1 (5)C31—C32—H32A119.3
N1—C1—C2112.7 (5)C32—C33—C28119.7 (6)
N1—C1—H1A109.1C32—C33—H33A120.1
C2—C1—H1A109.1C28—C33—H33A120.1
N1—C1—H1B109.1C31—C34—H34A109.5
C2—C1—H1B109.1C31—C34—H34B109.5
H1A—C1—H1B107.8H34A—C34—H34B109.5
N2—C2—C1109.2 (5)C31—C34—H34C109.5
N2—C2—H2A109.8H34A—C34—H34C109.5
C1—C2—H2A109.8H34B—C34—H34C109.5
N2—C2—H2B109.8N4—C35—C36127.6 (5)
C1—C2—H2B109.8N4—C35—H35A116.2
H2A—C2—H2B108.3C36—C35—H35A116.2
N1—C3—C4112.3 (5)C41—C36—C37118.6 (6)
N1—C3—H3A109.1C41—C36—C35124.3 (5)
C4—C3—H3A109.1C37—C36—C35117.1 (6)
N1—C3—H3B109.1C38—C37—C36122.1 (6)
C4—C3—H3B109.1C38—C37—H37A118.9
H3A—C3—H3B107.9C36—C37—H37A118.9
N3—C4—C3110.4 (5)C37—C38—N9116.0 (5)
N3—C4—H4A109.6C37—C38—C39118.4 (5)
C3—C4—H4A109.6N9—C38—C39125.5 (5)
N3—C4—H4B109.6C40—C39—C38120.4 (6)
C3—C4—H4B109.6C40—C39—H39A119.8
H4A—C4—H4B108.1C38—C39—H39A119.8
N1—C5—C6112.3 (5)C39—C40—C41120.3 (5)
N1—C5—H5A109.1C39—C40—H40A119.9
C6—C5—H5A109.1C41—C40—H40A119.9
N1—C5—H5B109.1O3—C41—C36121.7 (5)
C6—C5—H5B109.1O3—C41—C40118.3 (5)
H5A—C5—H5B107.9C36—C41—C40119.9 (6)
N4—C6—C5110.2 (4)C47—C42—C43119.7 (6)
N4—C6—H6A109.6C47—C42—N10116.8 (5)
C5—C6—H6A109.6C43—C42—N10123.4 (5)
N4—C6—H6B109.6C44—C43—C42119.1 (6)
C5—C6—H6B109.6C44—C43—H43A120.5
H6A—C6—H6B108.1C42—C43—H43A120.5
N3—C7—C8127.6 (6)C43—C44—C45121.9 (6)
N3—C7—H7A116.2C43—C44—H44A119.1
C8—C7—H7A116.2C45—C44—H44A119.1
C9—C8—C13119.7 (5)C44—C45—C46117.7 (6)
C9—C8—C7118.1 (6)C44—C45—C48120.4 (6)
C13—C8—C7122.2 (5)C46—C45—C48121.9 (6)
C10—C9—C8122.3 (6)C47—C46—C45121.2 (6)
C10—C9—H9A118.9C47—C46—H46A119.4
C8—C9—H9A118.9C45—C46—H46A119.4
C9—C10—C11118.1 (5)C42—C47—C46120.4 (5)
C9—C10—N5117.3 (6)C42—C47—H47A119.8
C11—C10—N5124.7 (6)C46—C47—H47A119.8
C12—C11—C10121.2 (6)C45—C48—H48A109.5
C12—C11—H11A119.4C45—C48—H48B109.5
C10—C11—H11A119.4H48A—C48—H48B109.5
C11—C12—C13121.8 (6)C45—C48—H48C109.5
C11—C12—H12A119.1H48A—C48—H48C109.5
C13—C12—H12A119.1H48B—C48—H48C109.5
O1—C13—C8122.3 (5)N1S—C1S—C2S177.8 (12)
O1—C13—C12120.9 (5)C1S—C2S—H2S1109.5
C8—C13—C12116.8 (5)C1S—C2S—H2S2109.5
C15—C14—C19119.2 (6)H2S1—C2S—H2S2109.5
C15—C14—N6126.2 (6)C1S—C2S—H2S3109.5
C19—C14—N6114.6 (5)H2S1—C2S—H2S3109.5
C14—C15—C16120.1 (6)H2S2—C2S—H2S3109.5
C14—C15—H15A120.0
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4OA···O1i0.931.762.624 (5)153
O4—H4OB···O3i0.832.002.761 (5)153
Symmetry code: (i) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formula[Sm(C48H45N10O3)(H2O)]·C2H3N
Mr1019.36
Crystal system, space groupMonoclinic, P21/c
Temperature (K)150
a, b, c (Å)19.9785 (5), 20.4849 (4), 11.4683 (8)
β (°) 95.3750 (14)
V3)4672.9 (4)
Z4
Radiation typeMo Kα
µ (mm1)1.31
Crystal size (mm)0.35 × 0.11 × 0.08
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correctionMulti-scan
(SORTAV; Blessing, 1995)
Tmin, Tmax0.727, 0.907
No. of measured, independent and
observed [I > 2σ(I)] reflections
32101, 10613, 5694
Rint0.105
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.128, 1.02
No. of reflections10613
No. of parameters598
No. of restraints2
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)2.91, 0.96

Computer programs: COLLECT (Nonius, 2002), DENZO-SMN (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1994), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009).

Selected bond lengths (Å) top
Sm1—O22.302 (4)Sm1—N22.556 (4)
Sm1—O32.321 (4)Sm1—N32.605 (5)
Sm1—O12.346 (3)Sm1—N42.671 (5)
Sm1—O42.432 (3)Sm1—N12.753 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4OA···O1i0.931.762.624 (5)153
O4—H4OB···O3i0.832.002.761 (5)153
Symmetry code: (i) x+1, y+1, z+1.
 

Acknowledgements

We are grateful to Bu-Ali Sina University for financial support.

References

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First citationOtwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.  Google Scholar
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