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

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ISSN: 2056-9890

A trinuclear cobalt–cerium complex: bis­­(2,2′-bi­pyridine)-1κ2N,N′;3κ2N,N′-hexa-μ-methacrylato-1:2κ6O:O′;2:3κ6O:O′-nitrato-2κ2O,O′-2-cerium(III)-1,3-dicobalt(II)

aDepartment of Applied Chemistry, Zhejiang Sci-Tech University, Hangzhou 310018, People's Republic of China
*Correspondence e-mail: chemdpwu@yahoo.com.cn

(Received 4 March 2010; accepted 18 March 2010; online 27 March 2010)

In the title trinuclear cobalt-cerium complex, [CeCo2(C4H5O2)6(NO3)(C10H8N2)2], the CeIII and each of the two CoII ions are bridged by three bidentate methacrylate ligands. The CeIII center is coordinated by six O atoms from six methacrylate ligands and two O atoms from the nitrate anion in a distorted square-anti­prismatic geometry. Each CoII ion is coordinated by three O atoms from three methacrylate ligands and two N atoms from a 2,2′-bipyridine ligand in a distorted trigonal-pyramidal geometry. In the crystal structure, ππ inter­actions between the aromatic rings [centroid–centroid distances of 3.816 (8) and 3.756 (8) Å] link the mol­ecules into chains propagated in [01[\overline{1}]]. Weak inter­molecular C—H⋯O hydrogen bonds further stabilize the crystal packing.

Related literature

For the crystal structures of analogous complexes, see: Wu & Guo (2004[Wu, B. & Guo, Y. (2004). Acta Cryst. E60, m1356-m1358.]); Zhu et al. (2004a[Zhu, Y., Lu, W.-M. & Chen, F. (2004a). Acta Cryst. E60, m963-m965.],b[Zhu, Y., Lu, W. & Chen, F. (2004b). Acta Cryst. E60, m1459-m1461.]; 2005[Zhu, Y., Lu, W.-M., Ma, M. & Chen, F. (2005). Acta Cryst. E61, m1610-m1612.]). For the preparation of CeL3·2H2O (HL = CH2C(CH3)COOH), see: Lu et al. (1995[Lu, W.-M., Wu, J.-B., Dong, N., Chun, W.-G., Gu, J.-M. & Liang, K.-L. (1995). Acta Cryst. C51, 1568-1570.]).

[Scheme 1]

Experimental

Crystal data
  • [CeCo2(C4H5O2)6(NO3)(C10H8N2)2]

  • Mr = 1142.84

  • Triclinic, [P \overline 1]

  • a = 11.4445 (8) Å

  • b = 13.6484 (9) Å

  • c = 16.5051 (10) Å

  • α = 104.108 (9)°

  • β = 99.937 (8)°

  • γ = 100.115 (7)°

  • V = 2398.0 (3) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 1.69 mm−1

  • T = 292 K

  • 0.35 × 0.30 × 0.28 mm

Data collection
  • Rigaku R-AXIS RAPID diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.559, Tmax = 0.623

  • 17512 measured reflections

  • 8121 independent reflections

  • 7037 reflections with I > 2σ(I)

  • Rint = 0.020

Refinement
  • R[F2 > 2σ(F2)] = 0.023

  • wR(F2) = 0.054

  • S = 1.03

  • 8121 reflections

  • 610 parameters

  • H-atom parameters constrained

  • Δρmax = 0.27 e Å−3

  • Δρmin = −0.36 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C2—H2⋯O7i 0.93 2.59 3.322 (4) 136
C3—H3⋯O9i 0.93 2.45 3.307 (5) 154
C7—H7⋯O3ii 0.93 2.58 3.452 (4) 156
C37—H37⋯O9iii 0.93 2.51 3.364 (4) 152
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+2, -y+1, -z+1; (iii) -x+1, -y+2, -z.

Data collection: RAPID-AUTO (Rigaku, 1998[Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002[Rigaku/MSC (2002). CrystalStructure. Rigaku and Rigaku/MSC, The Woodlands Texas, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

As a contribution to a structural study of heterometallic complexes containing d-transition metal and rare-earth(III) cations (Wu & Guo, 2004; Zhu et al., 2004a,b; Zhu et al., 2005), herewith we report the synthesis and crystal structure of the title compound.

The crystal structure of the title Co—Ce—Co trinuclear complex is similar to the known crystal structures of the Zn—Nd—Zn, Zn—Pr—Zn, Zn—La—Zn and Zn—Ce—Zn complexes (Wu & Guo, 2004; Zhu et al., 2004a,b; Zhu et al., 2005). The CeIII center is coordinated by six O atoms from six methacrylato ligands and two O atoms from nitrate anion in a distorted square-antiprismatic geometry. Each CoII ion is coordinated by three O atoms from three methacrylato ligands and two N atoms from 2,2'-bipyridine ligand in a distorted pyramidal geometry. The CeIII and each of two CoII ions are bridged by three bidentate methacrylato ligands. Two Ce···Co separations are almost equal being 3.944 (1) and 3.993 (1) Å, respectively.

In the crystal structure, π-π interactions between the aromatic rings (Table 1) link molecules into chains propagated in direction [01-1]. Weak intermolecular C—H···O hydrogen bonds (Table 2) stabilize further the crystal packing.

Related literature top

For the crystal structures of analogous complexes, see: Wu & Guo (2004); Zhu et al. (2004a,b; 2005). For the preparation of CeL3.2H2O (HL = CH2C(CH3)COOH), see: Lu et al. (1995).

Experimental top

CeL3.2H2O (870 mg, 2.0 mmol; HL = CH2C(CH3)COOH ) prepared in accordance with Lu et al. (1995) and Co(NO3)2.6H2O (435 mg, 1.5 mmol) were dissolved in 15 ml H2O, and the pH adjusted to 4.0 using HL. Three mililiters of ethanol solution 2,2'-bipyridine (234 mg, 1.5 mmol) were added into the mixed solution with stirring. After filtration, the filtrate was allowed to stand at room temperature and single crystals suitable for X-ray work were obtained after two weeks.

Refinement top

All H-atoms were placed in idealized locations with C–H distances 0.93 - 0.96 Å and refined as riding with Uiso(H) = 1.2 or 1.5 Uiso(C).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. View of the title molecule showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. All H atoms have been omitted for clarity.
bis(2,2'-bipyridine)-1κ2N,N';3κ2N,N'- hexa-µ-methacrylato-1:2κ6O:O';2:3κ6O:O'- nitrato-2κ2O,O'-2-cerium(III)-1,3-dicobalt(II) top
Crystal data top
[CeCo2(C4H5O2)6(NO3)(C10H8N2)2]Z = 2
Mr = 1142.84F(000) = 1154
Triclinic, P1Dx = 1.583 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71069 Å
a = 11.4445 (8) ÅCell parameters from 7585 reflections
b = 13.6484 (9) Åθ = 2.3–27.4°
c = 16.5051 (10) ŵ = 1.69 mm1
α = 104.108 (9)°T = 292 K
β = 99.937 (8)°Prism, brown
γ = 100.115 (7)°0.35 × 0.30 × 0.28 mm
V = 2398.0 (3) Å3
Data collection top
Rigaku R-AXIS RAPID
diffractometer
8121 independent reflections
Radiation source: fine-focus sealed tube7037 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
Detector resolution: 10.00 pixels mm-1θmax = 25.1°, θmin = 1.3°
ω scansh = 1313
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
k = 1616
Tmin = 0.559, Tmax = 0.623l = 1919
17512 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)] = 0.023Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.054H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0302P)2 + 0.5473P]
where P = (Fo2 + 2Fc2)/3
8121 reflections(Δ/σ)max = 0.002
610 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = 0.36 e Å3
Crystal data top
[CeCo2(C4H5O2)6(NO3)(C10H8N2)2]γ = 100.115 (7)°
Mr = 1142.84V = 2398.0 (3) Å3
Triclinic, P1Z = 2
a = 11.4445 (8) ÅMo Kα radiation
b = 13.6484 (9) ŵ = 1.69 mm1
c = 16.5051 (10) ÅT = 292 K
α = 104.108 (9)°0.35 × 0.30 × 0.28 mm
β = 99.937 (8)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer
8121 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
7037 reflections with I > 2σ(I)
Tmin = 0.559, Tmax = 0.623Rint = 0.020
17512 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0230 restraints
wR(F2) = 0.054H-atom parameters constrained
S = 1.03Δρmax = 0.27 e Å3
8121 reflectionsΔρmin = 0.36 e Å3
610 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
Ce0.646568 (11)0.762318 (11)0.257303 (8)0.03641 (5)
Co10.71543 (3)0.57517 (3)0.39854 (2)0.04127 (8)
Co20.71375 (3)0.90602 (2)0.080876 (19)0.03731 (8)
O10.56474 (17)0.46603 (15)0.31540 (12)0.0602 (5)
O20.62793 (16)0.57970 (14)0.25067 (13)0.0581 (5)
O30.86748 (15)0.69345 (14)0.44496 (12)0.0544 (4)
O40.84746 (16)0.75916 (17)0.33430 (12)0.0640 (5)
O50.62048 (16)0.66522 (16)0.46295 (12)0.0569 (5)
O60.64355 (18)0.79847 (17)0.40766 (11)0.0642 (5)
O70.42302 (17)0.68799 (17)0.26372 (13)0.0634 (5)
O80.46456 (18)0.85157 (17)0.27586 (14)0.0652 (5)
O90.2814 (2)0.7743 (2)0.27262 (18)0.1017 (10)
O100.71556 (17)0.94278 (15)0.27044 (15)0.0679 (6)
O110.66255 (16)1.01476 (15)0.16728 (12)0.0561 (5)
O120.52216 (16)0.73813 (17)0.11668 (12)0.0634 (5)
O130.54427 (14)0.82487 (14)0.02171 (11)0.0489 (4)
O140.78294 (19)0.7574 (2)0.15643 (13)0.0843 (7)
O150.80120 (15)0.79025 (14)0.03581 (12)0.0525 (4)
N10.73679 (17)0.49011 (16)0.48701 (13)0.0459 (5)
N20.83532 (18)0.48188 (17)0.35382 (13)0.0484 (5)
N30.3877 (2)0.7720 (2)0.27117 (16)0.0640 (7)
N40.73331 (16)0.98929 (15)0.00789 (12)0.0397 (4)
N50.89352 (17)1.00305 (16)0.13205 (12)0.0414 (5)
C10.6747 (2)0.4913 (2)0.54883 (18)0.0581 (7)
H10.61990.53400.55440.070*
C20.6889 (3)0.4319 (3)0.6042 (2)0.0711 (9)
H20.64370.43380.64610.085*
C30.7705 (3)0.3699 (3)0.5972 (2)0.0785 (10)
H30.78290.33020.63500.094*
C40.8341 (3)0.3668 (2)0.5334 (2)0.0663 (8)
H40.88930.32440.52720.080*
C50.8149 (2)0.4277 (2)0.47851 (16)0.0470 (6)
C60.8746 (2)0.42659 (19)0.40572 (16)0.0459 (6)
C70.9639 (3)0.3721 (2)0.3901 (2)0.0651 (8)
H70.99160.33530.42710.078*
C81.0106 (3)0.3733 (3)0.3193 (2)0.0779 (10)
H81.07000.33690.30760.093*
C90.9693 (3)0.4285 (3)0.2660 (2)0.0771 (10)
H90.99950.42930.21730.092*
C100.8826 (3)0.4828 (3)0.28554 (19)0.0637 (8)
H100.85600.52150.24990.076*
C110.5575 (2)0.4969 (2)0.24968 (17)0.0456 (6)
C120.4677 (2)0.4326 (2)0.16978 (16)0.0487 (6)
C130.3860 (3)0.3415 (3)0.1760 (2)0.0865 (11)
H13A0.33620.36270.21520.130*
H13B0.43310.29710.19650.130*
H13C0.33500.30450.12050.130*
C140.4674 (3)0.4585 (3)0.09614 (19)0.0747 (9)
H14A0.41310.41720.04580.090*
H14B0.52150.51760.09560.090*
C150.8992 (2)0.7601 (2)0.40809 (16)0.0453 (6)
C161.0064 (2)0.8472 (2)0.4549 (2)0.0555 (7)
C171.0254 (3)0.8825 (3)0.5413 (2)0.0812 (10)
H17A1.08990.93830.57170.097*
H17B0.97400.85110.57010.097*
C181.0817 (3)0.8911 (3)0.4038 (3)0.0993 (13)
H18A1.14060.95170.44000.149*
H18B1.03100.90960.35990.149*
H18C1.12300.84070.37770.149*
C190.6267 (2)0.7587 (2)0.46692 (16)0.0463 (6)
C200.6162 (2)0.8285 (2)0.54997 (16)0.0523 (7)
C210.6097 (3)0.7816 (3)0.62045 (19)0.0818 (10)
H21A0.60890.83380.67120.123*
H21B0.67930.75250.63120.123*
H21C0.53670.72790.60520.123*
C220.6135 (3)0.9272 (3)0.5566 (2)0.0879 (11)
H22A0.60730.97030.60800.106*
H22B0.61790.95300.50970.106*
C230.6811 (2)1.0143 (2)0.24425 (18)0.0467 (6)
C240.6657 (2)1.1069 (2)0.30774 (16)0.0482 (6)
C250.6632 (3)1.1034 (3)0.3872 (2)0.0760 (9)
H25A0.65221.16050.42680.091*
H25B0.67251.04390.40310.091*
C260.6518 (3)1.1977 (2)0.2777 (2)0.0721 (8)
H26A0.64501.25260.32440.108*
H26B0.57971.17960.23260.108*
H26C0.72161.22050.25630.108*
C270.4831 (2)0.76085 (19)0.05019 (15)0.0411 (5)
C280.3557 (2)0.7090 (2)0.00004 (17)0.0517 (6)
C290.2859 (3)0.6420 (3)0.0310 (3)0.0886 (12)
H29A0.20590.61050.00190.106*
H29B0.31820.62780.08150.106*
C300.3137 (3)0.7356 (3)0.0770 (2)0.0765 (9)
H30A0.35270.70500.12060.115*
H30B0.33330.80970.06590.115*
H30C0.22710.71000.09600.115*
C310.8207 (2)0.7411 (2)0.08925 (16)0.0455 (6)
C320.8997 (3)0.6651 (2)0.0737 (2)0.0587 (7)
C330.9661 (4)0.6462 (4)0.1427 (3)0.1169 (16)
H33A1.01900.60200.13480.140*
H33B0.95860.67760.19770.140*
C340.9059 (3)0.6198 (2)0.0135 (2)0.0739 (9)
H34A0.95460.56910.01480.111*
H34B0.94210.67310.03620.111*
H34C0.82530.58700.04750.111*
C350.6458 (2)0.9808 (2)0.07628 (17)0.0500 (6)
H350.57070.93590.08460.060*
C360.6625 (3)1.0360 (2)0.13475 (18)0.0587 (7)
H360.59991.02900.18140.070*
C370.7738 (3)1.1013 (2)0.12245 (19)0.0616 (8)
H370.78811.13880.16130.074*
C380.8641 (2)1.1111 (2)0.05225 (17)0.0512 (6)
H380.94001.15500.04340.061*
C390.8415 (2)1.05532 (18)0.00512 (15)0.0390 (5)
C400.9312 (2)1.06372 (18)0.08404 (15)0.0392 (5)
C411.0465 (2)1.1292 (2)0.10949 (17)0.0508 (6)
H411.07281.16960.07530.061*
C421.1214 (2)1.1339 (2)0.18549 (18)0.0585 (7)
H421.19831.17830.20350.070*
C431.0824 (2)1.0729 (2)0.23502 (18)0.0584 (7)
H431.13171.07520.28690.070*
C440.9683 (2)1.0083 (2)0.20546 (16)0.0520 (6)
H440.94180.96600.23820.062*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ce0.03874 (8)0.04090 (9)0.03799 (8)0.01186 (5)0.01074 (5)0.02308 (6)
Co10.04147 (17)0.0443 (2)0.04137 (19)0.01198 (14)0.00418 (14)0.02014 (15)
Co20.03676 (16)0.03833 (19)0.03931 (18)0.00528 (13)0.00993 (13)0.01688 (14)
O10.0639 (11)0.0597 (13)0.0508 (11)0.0093 (9)0.0065 (9)0.0215 (10)
O20.0504 (10)0.0411 (11)0.0814 (14)0.0080 (8)0.0158 (9)0.0157 (10)
O30.0470 (10)0.0486 (11)0.0671 (12)0.0086 (8)0.0019 (9)0.0250 (10)
O40.0488 (10)0.0902 (16)0.0533 (12)0.0172 (10)0.0020 (9)0.0263 (11)
O50.0580 (11)0.0572 (13)0.0633 (12)0.0199 (9)0.0213 (9)0.0213 (10)
O60.0829 (14)0.0824 (15)0.0441 (11)0.0366 (11)0.0239 (10)0.0291 (10)
O70.0554 (11)0.0738 (15)0.0812 (14)0.0163 (10)0.0258 (10)0.0505 (12)
O80.0638 (12)0.0733 (15)0.0840 (15)0.0334 (11)0.0304 (11)0.0468 (12)
O90.0588 (14)0.170 (3)0.139 (2)0.0587 (15)0.0532 (14)0.112 (2)
O100.0612 (12)0.0474 (12)0.1085 (17)0.0146 (9)0.0286 (11)0.0381 (12)
O110.0548 (11)0.0583 (13)0.0511 (12)0.0120 (9)0.0141 (9)0.0072 (9)
O120.0534 (11)0.0855 (15)0.0514 (12)0.0028 (10)0.0014 (9)0.0359 (11)
O130.0425 (9)0.0517 (11)0.0494 (10)0.0020 (8)0.0051 (8)0.0212 (9)
O140.0600 (12)0.145 (2)0.0551 (12)0.0286 (13)0.0293 (10)0.0264 (13)
O150.0555 (10)0.0451 (11)0.0603 (12)0.0157 (8)0.0117 (9)0.0189 (9)
N10.0424 (11)0.0491 (13)0.0478 (12)0.0083 (9)0.0031 (9)0.0233 (10)
N20.0480 (12)0.0488 (14)0.0487 (13)0.0124 (10)0.0083 (10)0.0154 (10)
N30.0511 (14)0.102 (2)0.0688 (16)0.0322 (14)0.0265 (12)0.0587 (15)
N40.0409 (10)0.0391 (12)0.0434 (11)0.0092 (8)0.0101 (9)0.0190 (9)
N50.0404 (10)0.0446 (12)0.0391 (11)0.0048 (9)0.0079 (9)0.0163 (9)
C10.0508 (15)0.070 (2)0.0617 (18)0.0106 (13)0.0121 (13)0.0353 (15)
C20.0696 (19)0.084 (2)0.071 (2)0.0069 (17)0.0211 (16)0.0457 (18)
C30.094 (2)0.076 (2)0.080 (2)0.0159 (19)0.0125 (19)0.056 (2)
C40.0725 (19)0.0546 (19)0.078 (2)0.0197 (15)0.0030 (16)0.0367 (16)
C50.0446 (13)0.0418 (15)0.0509 (15)0.0050 (11)0.0038 (11)0.0199 (12)
C60.0429 (13)0.0375 (15)0.0512 (15)0.0086 (10)0.0028 (11)0.0112 (12)
C70.0617 (18)0.056 (2)0.074 (2)0.0209 (14)0.0040 (15)0.0143 (16)
C80.067 (2)0.077 (2)0.087 (2)0.0355 (18)0.0144 (18)0.0062 (19)
C90.072 (2)0.092 (3)0.067 (2)0.0245 (19)0.0255 (17)0.0105 (19)
C100.0638 (18)0.075 (2)0.0558 (18)0.0204 (15)0.0142 (14)0.0212 (16)
C110.0394 (13)0.0395 (15)0.0571 (16)0.0132 (11)0.0066 (11)0.0122 (12)
C120.0505 (14)0.0485 (16)0.0451 (15)0.0105 (12)0.0033 (11)0.0152 (12)
C130.087 (2)0.075 (2)0.072 (2)0.0207 (18)0.0090 (18)0.0188 (19)
C140.100 (2)0.068 (2)0.0512 (18)0.0160 (18)0.0092 (17)0.0162 (16)
C150.0376 (12)0.0501 (16)0.0510 (16)0.0179 (11)0.0052 (11)0.0171 (12)
C160.0454 (14)0.0471 (17)0.074 (2)0.0128 (12)0.0026 (13)0.0238 (15)
C170.086 (2)0.057 (2)0.079 (2)0.0123 (17)0.0157 (18)0.0064 (17)
C180.073 (2)0.092 (3)0.139 (4)0.003 (2)0.026 (2)0.051 (3)
C190.0375 (13)0.064 (2)0.0428 (14)0.0189 (12)0.0092 (10)0.0197 (13)
C200.0494 (15)0.065 (2)0.0438 (15)0.0121 (13)0.0142 (11)0.0150 (13)
C210.094 (2)0.110 (3)0.0468 (18)0.028 (2)0.0213 (17)0.0252 (18)
C220.112 (3)0.066 (2)0.093 (3)0.017 (2)0.056 (2)0.014 (2)
C230.0335 (12)0.0405 (15)0.0653 (18)0.0013 (10)0.0158 (11)0.0151 (13)
C240.0419 (13)0.0495 (17)0.0496 (15)0.0049 (11)0.0078 (11)0.0132 (12)
C250.074 (2)0.096 (3)0.059 (2)0.0237 (18)0.0168 (16)0.0200 (18)
C260.081 (2)0.0507 (19)0.078 (2)0.0134 (16)0.0142 (17)0.0112 (16)
C270.0356 (12)0.0456 (15)0.0399 (13)0.0048 (10)0.0069 (10)0.0122 (11)
C280.0376 (13)0.0506 (17)0.0583 (17)0.0032 (11)0.0034 (11)0.0096 (13)
C290.0515 (18)0.090 (3)0.123 (3)0.0099 (17)0.0061 (18)0.055 (2)
C300.0545 (17)0.102 (3)0.063 (2)0.0082 (17)0.0100 (14)0.0282 (19)
C310.0364 (12)0.0514 (16)0.0473 (15)0.0054 (11)0.0117 (11)0.0130 (12)
C320.0608 (17)0.0503 (18)0.082 (2)0.0198 (13)0.0306 (15)0.0353 (15)
C330.136 (4)0.147 (4)0.112 (3)0.088 (3)0.034 (3)0.074 (3)
C340.086 (2)0.0485 (19)0.099 (3)0.0232 (16)0.044 (2)0.0212 (17)
C350.0458 (14)0.0542 (17)0.0558 (16)0.0125 (12)0.0093 (12)0.0268 (13)
C360.0621 (17)0.068 (2)0.0588 (18)0.0252 (15)0.0103 (14)0.0356 (15)
C370.078 (2)0.062 (2)0.0641 (19)0.0239 (15)0.0253 (16)0.0417 (16)
C380.0586 (16)0.0459 (16)0.0586 (17)0.0112 (12)0.0197 (13)0.0278 (13)
C390.0440 (13)0.0320 (13)0.0468 (14)0.0114 (10)0.0157 (10)0.0161 (11)
C400.0407 (12)0.0327 (13)0.0465 (14)0.0084 (10)0.0152 (10)0.0119 (11)
C410.0480 (14)0.0439 (16)0.0611 (17)0.0027 (11)0.0158 (13)0.0187 (13)
C420.0419 (14)0.0586 (19)0.0641 (18)0.0048 (12)0.0083 (13)0.0116 (14)
C430.0462 (15)0.073 (2)0.0483 (16)0.0022 (13)0.0031 (12)0.0159 (14)
C440.0429 (14)0.0661 (19)0.0472 (15)0.0032 (12)0.0084 (11)0.0243 (13)
Geometric parameters (Å, º) top
Ce—O102.3947 (19)C13—H13B0.9600
Ce—O62.4169 (17)C13—H13C0.9600
Ce—O122.4174 (18)C14—H14A0.9300
Ce—O22.4376 (18)C14—H14B0.9300
Ce—O42.4404 (18)C15—C161.493 (4)
Ce—O142.4681 (18)C16—C171.353 (4)
Ce—O72.6115 (18)C16—C181.460 (4)
Ce—O82.6165 (18)C17—H17A0.9300
Co1—O52.0130 (18)C17—H17B0.9300
Co1—O32.0424 (18)C18—H18A0.9600
Co1—N12.084 (2)C18—H18B0.9600
Co1—O12.0881 (19)C18—H18C0.9600
Co1—N22.134 (2)C19—C201.504 (4)
Co2—O132.0017 (16)C20—C221.331 (4)
Co2—O112.0352 (18)C20—C211.464 (4)
Co2—O152.0715 (17)C21—H21A0.9600
Co2—N42.0793 (18)C21—H21B0.9600
Co2—N52.1443 (19)C21—H21C0.9600
O1—C111.251 (3)C22—H22A0.9300
O2—C111.262 (3)C22—H22B0.9300
O3—C151.249 (3)C23—C241.490 (4)
O4—C151.255 (3)C24—C251.328 (4)
O5—C191.251 (3)C24—C261.467 (4)
O6—C191.255 (3)C25—H25A0.9300
O7—N31.267 (3)C25—H25B0.9300
O8—N31.248 (3)C26—H26A0.9600
O9—N31.226 (3)C26—H26B0.9600
O10—C231.256 (3)C26—H26C0.9600
O11—C231.253 (3)C27—C281.499 (3)
O12—C271.243 (3)C28—C291.359 (4)
O13—C271.254 (3)C28—C301.433 (4)
O14—C311.243 (3)C29—H29A0.9300
O15—C311.245 (3)C29—H29B0.9300
N1—C11.339 (3)C30—H30A0.9600
N1—C51.341 (3)C30—H30B0.9600
N2—C101.334 (3)C30—H30C0.9600
N2—C61.344 (3)C31—C321.497 (4)
N4—C351.340 (3)C32—C331.361 (5)
N4—C391.347 (3)C32—C341.441 (4)
N5—C441.336 (3)C33—H33A0.9300
N5—C401.346 (3)C33—H33B0.9300
C1—C21.369 (4)C34—H34A0.9600
C1—H10.9300C34—H34B0.9600
C2—C31.367 (5)C34—H34C0.9600
C2—H20.9300C35—C361.379 (4)
C3—C41.376 (4)C35—H350.9300
C3—H30.9300C36—C371.373 (4)
C4—C51.387 (4)C36—H360.9300
C4—H40.9300C37—C381.375 (4)
C5—C61.479 (4)C37—H370.9300
C6—C71.390 (4)C38—C391.382 (3)
C7—C81.367 (4)C38—H380.9300
C7—H70.9300C39—C401.479 (3)
C8—C91.367 (5)C40—C411.389 (3)
C8—H80.9300C41—C421.372 (4)
C9—C101.375 (4)C41—H410.9300
C9—H90.9300C42—C431.374 (4)
C10—H100.9300C42—H420.9300
C11—C121.490 (4)C43—C441.373 (4)
C12—C141.346 (4)C43—H430.9300
C12—C131.455 (4)C44—H440.9300
C13—H13A0.9600
Cg1···Cg1i3.816 (8)Cg2···Cg2ii3.756 (8)
O10—Ce—O691.79 (8)C12—C13—H13B109.5
O10—Ce—O1289.98 (7)H13A—C13—H13B109.5
O6—Ce—O12143.18 (7)C12—C13—H13C109.5
O10—Ce—O2166.37 (6)H13A—C13—H13C109.5
O6—Ce—O288.83 (7)H13B—C13—H13C109.5
O12—Ce—O297.67 (7)C12—C14—H14A120.0
O10—Ce—O490.23 (7)C12—C14—H14B120.0
O6—Ce—O472.74 (6)H14A—C14—H14B120.0
O12—Ce—O4144.04 (7)O3—C15—O4124.7 (2)
O2—Ce—O476.95 (7)O3—C15—C16117.8 (2)
O10—Ce—O1478.17 (8)O4—C15—C16117.5 (2)
O6—Ce—O14143.45 (7)C17—C16—C18124.2 (3)
O12—Ce—O1472.62 (7)C17—C16—C15118.3 (3)
O2—Ce—O1493.31 (8)C18—C16—C15117.4 (3)
O4—Ce—O1472.25 (7)C16—C17—H17A120.0
O10—Ce—O7120.53 (7)C16—C17—H17B120.0
O6—Ce—O773.78 (7)H17A—C17—H17B120.0
O12—Ce—O773.76 (6)C16—C18—H18A109.5
O2—Ce—O772.66 (6)C16—C18—H18B109.5
O4—Ce—O7134.65 (6)H18A—C18—H18B109.5
O14—Ce—O7141.25 (7)C16—C18—H18C109.5
O10—Ce—O871.94 (7)H18A—C18—H18C109.5
O6—Ce—O874.02 (6)H18B—C18—H18C109.5
O12—Ce—O871.65 (7)O5—C19—O6124.9 (2)
O2—Ce—O8121.17 (6)O5—C19—C20117.0 (2)
O4—Ce—O8141.52 (7)O6—C19—C20118.1 (3)
O14—Ce—O8132.74 (7)C22—C20—C21123.5 (3)
O7—Ce—O848.59 (7)C22—C20—C19120.1 (3)
O5—Co1—O389.76 (8)C21—C20—C19116.4 (3)
O5—Co1—N194.40 (8)C20—C21—H21A109.5
O3—Co1—N1101.83 (8)C20—C21—H21B109.5
O5—Co1—O196.44 (8)H21A—C21—H21B109.5
O3—Co1—O1161.94 (8)C20—C21—H21C109.5
N1—Co1—O194.60 (8)H21A—C21—H21C109.5
O5—Co1—N2169.14 (8)H21B—C21—H21C109.5
O3—Co1—N285.59 (8)C20—C22—H22A120.0
N1—Co1—N277.00 (8)C20—C22—H22B120.0
O1—Co1—N290.93 (8)H22A—C22—H22B120.0
O13—Co2—O1195.51 (7)O11—C23—O10123.8 (3)
O13—Co2—O1596.45 (7)O11—C23—C24117.1 (2)
O11—Co2—O15158.37 (8)O10—C23—C24119.1 (3)
O13—Co2—N495.64 (7)C25—C24—C26123.3 (3)
O11—Co2—N497.37 (8)C25—C24—C23119.6 (3)
O15—Co2—N499.30 (7)C26—C24—C23117.2 (2)
O13—Co2—N5172.77 (7)C24—C25—H25A120.0
O11—Co2—N585.03 (7)C24—C25—H25B120.0
O15—Co2—N585.35 (7)H25A—C25—H25B120.0
N4—Co2—N577.15 (7)C24—C26—H26A109.5
C11—O1—Co1101.33 (16)C24—C26—H26B109.5
C11—O2—Ce145.62 (16)H26A—C26—H26B109.5
C15—O3—Co1124.83 (16)C24—C26—H26C109.5
C15—O4—Ce138.76 (16)H26A—C26—H26C109.5
C19—O5—Co1124.84 (16)H26B—C26—H26C109.5
C19—O6—Ce144.81 (19)O12—C27—O13123.9 (2)
N3—O7—Ce96.76 (15)O12—C27—C28118.8 (2)
N3—O8—Ce97.03 (15)O13—C27—C28117.3 (2)
C23—O10—Ce140.38 (18)C29—C28—C30123.9 (3)
C23—O11—Co2119.12 (17)C29—C28—C27118.5 (3)
C27—O12—Ce157.24 (18)C30—C28—C27117.6 (2)
C27—O13—Co2123.64 (15)C28—C29—H29A120.0
C31—O14—Ce161.91 (19)C28—C29—H29B120.0
C31—O15—Co2110.43 (16)H29A—C29—H29B120.0
C1—N1—C5118.7 (2)C28—C30—H30A109.5
C1—N1—Co1124.28 (17)C28—C30—H30B109.5
C5—N1—Co1116.93 (16)H30A—C30—H30B109.5
C10—N2—C6118.8 (2)C28—C30—H30C109.5
C10—N2—Co1125.82 (19)H30A—C30—H30C109.5
C6—N2—Co1115.00 (16)H30B—C30—H30C109.5
O9—N3—O8121.6 (3)O14—C31—O15122.4 (3)
O9—N3—O7120.8 (3)O14—C31—C32119.5 (3)
O8—N3—O7117.5 (2)O15—C31—C32117.9 (2)
C35—N4—C39118.9 (2)C33—C32—C34123.5 (3)
C35—N4—Co2124.13 (16)C33—C32—C31118.4 (3)
C39—N4—Co2117.00 (15)C34—C32—C31118.0 (3)
C44—N5—C40118.8 (2)C32—C33—H33A120.0
C44—N5—Co2126.25 (16)C32—C33—H33B120.0
C40—N5—Co2114.96 (15)H33A—C33—H33B120.0
N1—C1—C2122.5 (3)C32—C34—H34A109.5
N1—C1—H1118.8C32—C34—H34B109.5
C2—C1—H1118.8H34A—C34—H34B109.5
C3—C2—C1119.1 (3)C32—C34—H34C109.5
C3—C2—H2120.5H34A—C34—H34C109.5
C1—C2—H2120.5H34B—C34—H34C109.5
C2—C3—C4119.3 (3)N4—C35—C36122.6 (2)
C2—C3—H3120.4N4—C35—H35118.7
C4—C3—H3120.4C36—C35—H35118.7
C3—C4—C5119.1 (3)C37—C36—C35118.4 (3)
C3—C4—H4120.5C37—C36—H36120.8
C5—C4—H4120.5C35—C36—H36120.8
N1—C5—C4121.3 (3)C36—C37—C38119.5 (2)
N1—C5—C6115.3 (2)C36—C37—H37120.3
C4—C5—C6123.3 (2)C38—C37—H37120.3
N2—C6—C7121.3 (3)C37—C38—C39119.6 (2)
N2—C6—C5115.1 (2)C37—C38—H38120.2
C7—C6—C5123.5 (2)C39—C38—H38120.2
C8—C7—C6119.0 (3)N4—C39—C38121.0 (2)
C8—C7—H7120.5N4—C39—C40115.50 (19)
C6—C7—H7120.5C38—C39—C40123.5 (2)
C9—C8—C7119.6 (3)N5—C40—C41120.7 (2)
C9—C8—H8120.2N5—C40—C39115.3 (2)
C7—C8—H8120.2C41—C40—C39124.0 (2)
C8—C9—C10119.0 (3)C42—C41—C40119.5 (2)
C8—C9—H9120.5C42—C41—H41120.3
C10—C9—H9120.5C40—C41—H41120.3
N2—C10—C9122.3 (3)C41—C42—C43119.9 (2)
N2—C10—H10118.8C41—C42—H42120.1
C9—C10—H10118.8C43—C42—H42120.1
O1—C11—O2120.3 (2)C42—C43—C44117.8 (3)
O1—C11—C12118.9 (2)C42—C43—H43121.1
O2—C11—C12120.8 (2)C44—C43—H43121.1
C14—C12—C13123.4 (3)N5—C44—C43123.4 (2)
C14—C12—C11119.8 (3)N5—C44—H44118.3
C13—C12—C11116.8 (2)C43—C44—H44118.3
C12—C13—H13A109.5
Symmetry codes: (i) x+2, y+1, z+1; (ii) x+2, y+2, z.
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the N1/N2/C1–C10 and N4/N5/C35–C40 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C2—H2···O7iii0.932.593.322 (4)136
C3—H3···O9iii0.932.453.307 (5)154
C7—H7···O3i0.932.583.452 (4)156
C29—H29B···O120.932.432.750 (4)100
C37—H37···O9iv0.932.513.364 (4)152
Symmetry codes: (i) x+2, y+1, z+1; (iii) x+1, y+1, z+1; (iv) x+1, y+2, z.

Experimental details

Crystal data
Chemical formula[CeCo2(C4H5O2)6(NO3)(C10H8N2)2]
Mr1142.84
Crystal system, space groupTriclinic, P1
Temperature (K)292
a, b, c (Å)11.4445 (8), 13.6484 (9), 16.5051 (10)
α, β, γ (°)104.108 (9), 99.937 (8), 100.115 (7)
V3)2398.0 (3)
Z2
Radiation typeMo Kα
µ (mm1)1.69
Crystal size (mm)0.35 × 0.30 × 0.28
Data collection
DiffractometerRigaku R-AXIS RAPID
diffractometer
Absorption correctionMulti-scan
(ABSCOR; Higashi, 1995)
Tmin, Tmax0.559, 0.623
No. of measured, independent and
observed [I > 2σ(I)] reflections
17512, 8121, 7037
Rint0.020
(sin θ/λ)max1)0.597
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.023, 0.054, 1.03
No. of reflections8121
No. of parameters610
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.27, 0.36

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the N1/N2/C1–C10 and N4/N5/C35–C40 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C2—H2···O7i0.932.593.322 (4)136
C3—H3···O9i0.932.453.307 (5)154
C7—H7···O3ii0.932.583.452 (4)156
C37—H37···O9iii0.932.513.364 (4)152
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+2, y+1, z+1; (iii) x+1, y+2, z.
 

Acknowledgements

This work was supported by the Natural Science Foundation of Zhejiang Province (M203105).

References

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First citationRigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationRigaku/MSC (2002). CrystalStructure. Rigaku and Rigaku/MSC, The Woodlands Texas, USA.  Google Scholar
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First citationZhu, Y., Lu, W.-M. & Chen, F. (2004a). Acta Cryst. E60, m963–m965.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationZhu, Y., Lu, W. & Chen, F. (2004b). Acta Cryst. E60, m1459–m1461.  Web of Science CSD CrossRef IUCr Journals Google Scholar
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