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The title complex, (nBu4N)+[(HCPz3)Ce(NO3)4] or (C16H36N)[Ce(NO3)4(C10H10N6)], which is the first lanthan­ide(III) complex of tris­(pyrazolyl)­methane (HCPz3), is 11-coordinate. The Ce—O and Ce—N bond lengths are in the ranges 2.514 (3)–2.685 (3) and 2.686 (4)–2.761 (4) Å, respectively.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802021177/ob6192sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802021177/ob6192Isup2.hkl
Contains datablock I

CCDC reference: 202302

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.009 Å
  • R factor = 0.043
  • wR factor = 0.092
  • Data-to-parameter ratio = 15.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Comment top

The coordination chemistry of the neutral isoelectronic carbon-centred analogue tris(pyrazolyl)methane (HCPz3) is relatively underdeveloped, even though it was introduced by Trofimenko as early as 1986 (Trofimenko, 1986). So far, many transition metal complexes with HCPz3 have been prepared (Astley et al., 1993; Bhambri et al., 1997; Reger et al., 1996) and main group element complexes have also appeared (Pettinari et al., 1999; Reger et al., 1997). However, no rare earth complexes with this remarkable tridentate ligand has been reported. Herein we report the title CeIII complex, (I).

The crystal structure of (I) consists of discrete [(HCPz3)Ce(NO3)4] and nBu4N+ ions. The structure of the anion is shown in Fig. 1. The cerium(III) ion is surrounded by three N atoms from the tridentate HCPz3 ligand and eight O atoms belonging to four bidentate chelating nitrate ligands. This structure is similar to the 11–coordinate Ce-nitrate complexes CeIII(NO3)4(R3TPTZ) [R is (CH3)3C and TPTZ is 2,4,6-tris(2-pyridyl)-1,3,5-triazine; Gabriel et al., 1996] and (Hpy)[CeIV(NO3)4(terpy)].py (terpy is terpyridine; Grigoriev et al., 2001). The Ce—O bond distances are in the range 2.514 (3)–2.685 (3) Å, and the shortest and longest Ce—O distances are slightly shorter than those in CeIII(NO3)4(R3TPTZ) [Ce—O 2.522 (7)–2.699 (9) Å] and (Hpy)[CeIV(NO3)4(terpy)].py [Ce—O 2.570 (2)–2.709 (2)°]. They are also comparable to those in ten-coordinate CeIII complexes, for example [(C6H5)3C2H5P]2Ce(NO3)5 [mean 2.57 (3) Å; Al-Karaghouli et al., 1973] and [Ce(ntb)(NO3)3]·H2O [ntb is tris(benzimidazol-2-ylmethyl)amine; mean 2.597 (2) Å; Su et al., 1998]. The nitrate ligands are coordinated to the cerium(III) ion in a slightly asymmetrical manner, with differences in the Ce···O distancess of 0.176 (2), 0.022 (2), 0.065 (2) and 0.065 (2) Å for the individual nitrate groups. CeIII is approximately coplanar with the nitrate ligands. The average dihedral angle of the chelating nitrate ligands is 48°. The CeIII—N distances are in the range 2.686 (4)–2.761 (4) Å; however, the shortest and longest Ce—N distances are slightly longer than those in CeIII(NO3)4(R3TPTZ) [Ce—N 2.673 (7)–2.734 (7) Å] and (Hpy)[CeIV(NO3)4(terpy)].py [Ce—N 2.624 (2)–2.706 (2) Å]. The three dihedral angles of the tridentate ligand are in the range 63.53 (13)–70.10 (13)°, and are larger than those of CeIII(NO3)4(R3TPTZ) [dihedral angle 59.4 (2)–62.4 (2)°] and (Hpy)[CeIV(NO3)4(terpy)].py [dihedral angle 57.68 (7)–61.37 (7)°]. There are intermolecular C—H···O close contacts leading to a three-dimensional polymeric network (Fig. 2 and Table 2).

Experimental top

All the chemicals used are commercially available, except for HCPz3, which was prepared according to the literature method of Reger (2000). Elemental analyses were carried on a Perkin-Elmer 240 C elemental analyzer. To an ethanol (25 ml) solution containing Ce(NO3)3·6H2O (0.5 mmol) was added stepwise HCPz3 (0.5 mmol) and nBu4NBr (0.5 mmol), and the reaction mixture refluxed for 30 min with stirring and then filtered. The filtrate was allowed to stand in air for several days, producing colorless rod-like crystals of (I) (yield ca 70%). Analysis calculated: C 36.96, H 5.49, N 18.24%; found: C 36.91, H 5.55, N 18.28%. 1H NMR (500 MHz, DMSO): δ (p.p.m.) 7.89 and 7.66 (d, d, 3H, 3H, 3-H and 5-H on Pz), 6.42 (t, 3H, 4-H on Pz), 8.97 (s, 1H on HCPz3), 3.16 and 0.93 (t, t, 8H, 8H, CH2 and CH3 on nBu4N), 1.56 and 1.30 (m, m, 8H, 8H, CH2 and CH2 on nBu4N).

Refinement top

The H atoms were generated geometrically.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. View of the [(HCPz3)Ce(NO3)4] anion, with displacement ellipsoids at the 20% probability level.
[Figure 2] Fig. 2. The crystal packing of compound (I), showing C—H···O short contacts along the c axis.
Tetrabutylammonium tetrakis(nitrato-κ2O,O')[1,3,5-tris(pyrazolyl)methane-κ3N]cerate(III) top
Crystal data top
(C16H36N)[Ce(NO3)4(C10H10N6)]F(000) = 1732
Mr = 844.86Dx = 1.507 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4597 reflections
a = 12.484 (1) Åθ = 2.2–23.8°
b = 16.742 (1) ŵ = 1.29 mm1
c = 18.267 (1) ÅT = 293 K
β = 102.82 (1)°Rod-like, colorless
V = 3722.8 (4) Å30.3 × 0.2 × 0.2 mm
Z = 4
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
6546 independent reflections
Radiation source: fine-focus sealed tube4018 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
ϕ and ω scansθmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan
(Sheldrick, 1990)
h = 1414
Tmin = 0.740, Tmax = 0.771k = 019
18988 measured reflectionsl = 021
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.03P)2 + 1.99P]
where P = (Fo2 + 2Fc2)/3
6546 reflections(Δ/σ)max < 0.001
431 parametersΔρmax = 0.67 e Å3
0 restraintsΔρmin = 0.59 e Å3
Crystal data top
(C16H36N)[Ce(NO3)4(C10H10N6)]V = 3722.8 (4) Å3
Mr = 844.86Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.484 (1) ŵ = 1.29 mm1
b = 16.742 (1) ÅT = 293 K
c = 18.267 (1) Å0.3 × 0.2 × 0.2 mm
β = 102.82 (1)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
6546 independent reflections
Absorption correction: multi-scan
(Sheldrick, 1990)
4018 reflections with I > 2σ(I)
Tmin = 0.740, Tmax = 0.771Rint = 0.037
18988 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.092H-atom parameters constrained
S = 1.02Δρmax = 0.67 e Å3
6546 reflectionsΔρmin = 0.59 e Å3
431 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. The structure was solved by direct method and refined by full-matrix least-square calculation on F2 using SHELXTL. All non-hydrogen atoms were refined anisotropically. 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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

3.8608 (0.0180) x + 15.3608 (0.0140) y − 5.7084 (0.0323) z = 11.5998 (0.0121)

* −0.0531 (0.0016) Ce1 * 0.0667 (0.0019) O1 * 0.0574 (0.0018) O2 * −0.0658 (0.0027) O3 * −0.0052 (0.0037) N7

Rms deviation of fitted atoms = 0.0546

3.9089 (0.0218) x − 1.9296 (0.0176) y + 15.5218 (0.0190) z = 2.5577 (0.0116)

Angle to previous plane (with approximate e.s.d.) = 75.84 (13)

* 0.0153 (0.0014) Ce1 * −0.0085 (0.0017) O4 * −0.0084 (0.0018) O5 * 0.0289 (0.0024) O6 * −0.0272 (0.0036) N8

Rms deviation of fitted atoms = 0.0198

4.9515 (0.0149) x + 15.1257 (0.0063) y − 4.5045 (0.0344) z = 11.9365 (0.0097)

Angle to previous plane (with approximate e.s.d.) = 82.34 (13)

* −0.0347 (0.0015) Ce1 * 0.0375 (0.0019) O7 * 0.0386 (0.0019) O8 * −0.0462 (0.0025) O9 * 0.0047 (0.0039) N9

Rms deviation of fitted atoms = 0.0354

4.9620 (0.0225) x + 3.5227 (0.0182) y + 14.2977 (0.0192) z = 6.7222 (0.0125)

Angle to previous plane (with approximate e.s.d.) = 78.32 (13)

* 0.0124 (0.0014) Ce1 * −0.0068 (0.0017) O10 * −0.0079 (0.0017) O11 * 0.0229 (0.0024) O12 * −0.0207 (0.0036) N10

Rms deviation of fitted atoms = 0.0156

3.8608 (0.0180) x + 15.3608 (0.0140) y − 5.7084 (0.0323) z = 11.5998 (0.0121)

Angle to previous plane (with approximate e.s.d.) = 84.69 (12)

* −0.0531 (0.0016) Ce1 * 0.0667 (0.0019) O1 * 0.0574 (0.0018) O2 * −0.0658 (0.0027) O3 * −0.0052 (0.0037) N7

Rms deviation of fitted atoms = 0.0546

4.9515 (0.0149) x + 15.1257 (0.0063) y − 4.5045 (0.0344) z = 11.9365 (0.0097)

Angle to previous plane (with approximate e.s.d.) = 7.13 (16)

* −0.0347 (0.0015) Ce1 * 0.0375 (0.0019) O7 * 0.0386 (0.0019) O8 * −0.0462 (0.0025) O9 * 0.0047 (0.0039) N9

Rms deviation of fitted atoms = 0.0354

3.9089 (0.0218) x − 1.9296 (0.0176) y + 15.5218 (0.0190) z = 2.5577 (0.0116)

Angle to previous plane (with approximate e.s.d.) = 82.34 (13)

* 0.0153 (0.0014) Ce1 * −0.0085 (0.0017) O4 * −0.0084 (0.0018) O5 * 0.0289 (0.0024) O6 * −0.0272 (0.0036) N8

Rms deviation of fitted atoms = 0.0198

4.9620 (0.0225) x + 3.5227 (0.0182) y + 14.2977 (0.0192) z = 6.7222 (0.0125)

Angle to previous plane (with approximate e.s.d.) = 19.58 (19)

* 0.0124 (0.0014) Ce1 * −0.0068 (0.0017) O10 * −0.0079 (0.0017) O11 * 0.0229 (0.0024) O12 * −0.0207 (0.0036) N10

Rms deviation of fitted atoms = 0.0156

4.0705 (0.0228) x + 15.8142 (0.0113) y − 2.0003 (0.0435) z = 13.0596 (0.0189)

Angle to previous plane (with approximate e.s.d.) = 72.88 (16)

* −0.0404 (0.0032) N1 * −0.0539 (0.0039) N2 * 0.0404 (0.0034) C17 * 0.0265 (0.0036) C18 * −0.0293 (0.0035) C19 * 0.0567 (0.0027) C26

Rms deviation of fitted atoms = 0.0427

− 8.7565 (0.0166) x + 11.1267 (0.0271) y − 1.7441 (0.0446) z = 5.1909 (0.0371)

Angle to previous plane (with approximate e.s.d.) = 65.87 (14)

* −0.0034 (0.0034) N3 * −0.0048 (0.0041) N4 * 0.0000 (0.0037) C20 * 0.0104 (0.0040) C21 * −0.0098 (0.0039) C22 * 0.0077 (0.0027) C26

Rms deviation of fitted atoms = 0.0070

11.8325 (0.0074) x + 5.3375 (0.0285) y − 3.8004 (0.0447) z = 6.6262 (0.0235)

Angle to previous plane (with approximate e.s.d.) = 63.03 (12)

* −0.0302 (0.0032) N5 * −0.0495 (0.0039) N6 * 0.0236 (0.0035) C23 * 0.0426 (0.0037) C24 * −0.0417 (0.0036) C25 * 0.0553 (0.0027) C26

Rms deviation of fitted atoms = 0.0419

4.0705 (0.0228) x + 15.8142 (0.0113) y − 2.0003 (0.0435) z = 13.0596 (0.0189)

Angle to previous plane (with approximate e.s.d.) = 52.40 (17)

* −0.0404 (0.0032) N1 * −0.0539 (0.0039) N2 * 0.0404 (0.0034) C17 * 0.0265 (0.0036) C18 * −0.0293 (0.0035) C19 * 0.0567 (0.0027) C26

Rms deviation of fitted atoms = 0.0427

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ce10.27896 (2)0.751820 (18)0.188978 (13)0.04547 (10)
C170.0804 (4)0.8436 (3)0.2842 (3)0.0556 (13)
H170.03270.85370.23830.067*
C180.0574 (5)0.8576 (3)0.3545 (3)0.0583 (14)
H180.00820.87720.36350.070*
C190.1450 (4)0.8379 (3)0.4056 (3)0.0573 (14)
H190.15310.84120.45730.069*
C200.4892 (4)0.8975 (3)0.2935 (3)0.0656 (15)
H200.51300.90900.24980.079*
C210.5249 (5)0.9368 (3)0.3594 (3)0.0694 (16)
H210.57450.97900.36880.083*
C220.4732 (5)0.9020 (3)0.4081 (3)0.0669 (16)
H220.48110.91480.45850.080*
C230.3969 (4)0.6060 (3)0.3372 (3)0.0578 (14)
H230.40380.56900.30060.069*
C240.4292 (4)0.5921 (3)0.4132 (3)0.0602 (14)
H240.46240.54650.43700.072*
C250.4024 (4)0.6588 (3)0.4456 (3)0.0591 (14)
H250.41110.66750.49680.071*
C260.3352 (4)0.7938 (3)0.4003 (3)0.0569 (13)
H260.34830.80400.45440.068*
N10.1811 (3)0.8137 (2)0.2931 (2)0.0526 (11)
N20.2214 (4)0.8120 (2)0.3686 (2)0.0544 (11)
N30.4163 (3)0.8406 (3)0.2984 (2)0.0604 (12)
N40.4086 (4)0.8457 (3)0.3702 (2)0.0605 (12)
N50.3549 (3)0.6787 (3)0.3225 (2)0.0550 (11)
N60.3607 (3)0.7108 (3)0.3907 (2)0.0554 (11)
N70.0659 (3)0.7650 (2)0.0718 (2)0.0550 (11)
N80.1809 (4)0.5866 (3)0.1904 (2)0.0585 (11)
N90.4582 (4)0.6755 (3)0.1210 (3)0.0585 (12)
N100.3256 (3)0.9148 (3)0.1303 (2)0.0574 (11)
O10.1584 (2)0.74174 (18)0.05932 (15)0.04547 (10)
O20.0681 (2)0.79130 (19)0.13329 (16)0.04547 (10)
O30.0148 (3)0.7626 (3)0.0214 (2)0.1093 (17)
O40.2709 (3)0.5962 (2)0.17014 (18)0.0587 (9)
O50.1366 (2)0.64561 (19)0.21009 (16)0.04547 (10)
O60.1454 (3)0.5187 (2)0.1945 (2)0.0854 (12)
O70.3677 (3)0.6951 (2)0.07995 (17)0.0563 (9)
O80.4732 (3)0.6932 (2)0.18926 (19)0.0576 (9)
O90.5279 (3)0.6416 (2)0.0950 (2)0.0752 (11)
O100.2484 (2)0.90512 (18)0.16047 (15)0.04547 (10)
O110.3836 (3)0.8539 (2)0.12609 (18)0.0578 (9)
O120.3508 (3)0.9800 (2)0.1086 (2)0.0870 (13)
N110.1736 (4)0.1421 (3)0.2403 (3)0.0833 (15)
C10.1556 (5)0.0313 (4)0.4948 (3)0.096 (2)
H1A0.13070.08310.50650.144*
H1B0.20290.00910.53870.144*
H1C0.09340.00310.47840.144*
C20.2181 (5)0.0392 (4)0.4330 (3)0.0864 (19)
H2A0.28480.06960.45170.104*
H2B0.23920.01350.41930.104*
C30.1522 (5)0.0796 (4)0.3645 (3)0.0833 (18)
H3A0.08560.04940.34520.100*
H3B0.13120.13260.37760.100*
C40.2174 (5)0.0858 (4)0.3058 (3)0.0816 (18)
H4A0.22340.03280.28560.098*
H4B0.29110.10300.32970.098*
C50.2568 (5)0.1428 (4)0.1911 (3)0.0847 (19)
H5A0.32830.15510.22250.102*
H5B0.26080.08940.17130.102*
C60.2348 (5)0.2002 (4)0.1266 (4)0.091 (2)
H6A0.16730.18510.09170.109*
H6B0.22510.25340.14500.109*
C70.3263 (5)0.2012 (4)0.0865 (4)0.094 (2)
H7A0.39510.21170.12190.113*
H7B0.33190.14940.06370.113*
C80.3068 (6)0.2622 (4)0.0290 (4)0.104 (2)
H8A0.23320.25730.00050.156*
H8B0.35800.25590.00280.156*
H8C0.31630.31390.05220.156*
C90.3220 (6)0.3919 (4)0.3758 (4)0.109 (2)
H9A0.35750.36140.41880.163*
H9B0.29760.44200.39200.163*
H9C0.37290.40170.34440.163*
C100.2285 (5)0.3479 (4)0.3339 (4)0.097 (2)
H10A0.19580.37760.28880.116*
H10B0.17390.34330.36400.116*
C110.2581 (5)0.2674 (4)0.3124 (4)0.091 (2)
H11A0.28970.23680.35710.109*
H11B0.31260.27140.28210.109*
C120.1566 (5)0.2253 (4)0.2683 (4)0.087 (2)
H12A0.10360.22190.29980.105*
H12B0.12440.25820.22540.105*
C130.0590 (5)0.1200 (4)0.1958 (4)0.093 (2)
H13A0.00960.11820.23000.111*
H13B0.03310.16170.15930.111*
C140.0530 (5)0.0413 (5)0.1552 (4)0.102 (2)
H14A0.08350.00030.19070.123*
H14B0.09710.04410.11780.123*
C150.0646 (6)0.0198 (5)0.1173 (4)0.110 (2)
H15A0.06500.03470.09930.132*
H15B0.10830.02090.15500.132*
C160.1203 (6)0.0711 (5)0.0532 (4)0.132 (3)
H16A0.12930.12400.07110.158*
H16B0.19110.04900.03110.158*
H16C0.07650.07320.01620.158*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ce10.03753 (15)0.06274 (18)0.03704 (15)0.00008 (15)0.01023 (10)0.00146 (16)
C170.056 (3)0.066 (4)0.048 (3)0.003 (3)0.019 (3)0.005 (3)
C180.060 (4)0.068 (4)0.050 (3)0.002 (3)0.020 (3)0.007 (3)
C190.063 (4)0.066 (4)0.047 (3)0.000 (3)0.020 (3)0.004 (3)
C200.061 (4)0.073 (4)0.058 (3)0.015 (3)0.003 (3)0.002 (3)
C210.065 (4)0.074 (4)0.063 (4)0.015 (3)0.000 (3)0.006 (3)
C220.065 (4)0.072 (4)0.058 (4)0.011 (3)0.001 (3)0.008 (3)
C230.063 (4)0.062 (4)0.047 (3)0.003 (3)0.007 (3)0.002 (3)
C240.066 (4)0.063 (4)0.048 (3)0.002 (3)0.006 (3)0.004 (3)
C250.065 (4)0.065 (4)0.044 (3)0.001 (3)0.006 (3)0.004 (3)
C260.061 (4)0.063 (4)0.045 (3)0.001 (3)0.009 (3)0.002 (3)
N10.056 (3)0.063 (3)0.042 (2)0.002 (2)0.017 (2)0.002 (2)
N20.060 (3)0.063 (3)0.043 (2)0.001 (2)0.017 (2)0.003 (2)
N30.056 (3)0.070 (3)0.051 (3)0.011 (2)0.002 (2)0.001 (2)
N40.060 (3)0.067 (3)0.051 (3)0.009 (2)0.004 (2)0.005 (2)
N50.057 (3)0.063 (3)0.043 (3)0.003 (2)0.007 (2)0.001 (2)
N60.061 (3)0.063 (3)0.041 (3)0.002 (2)0.008 (2)0.002 (2)
N70.043 (2)0.077 (3)0.043 (2)0.006 (2)0.004 (2)0.008 (2)
N80.053 (3)0.062 (3)0.062 (3)0.002 (2)0.015 (2)0.006 (2)
N90.043 (3)0.081 (3)0.054 (3)0.009 (2)0.017 (2)0.000 (2)
N100.050 (3)0.069 (3)0.057 (3)0.002 (2)0.020 (2)0.006 (2)
O10.03753 (15)0.06274 (18)0.03704 (15)0.00008 (15)0.01023 (10)0.00146 (16)
O20.03753 (15)0.06274 (18)0.03704 (15)0.00008 (15)0.01023 (10)0.00146 (16)
O30.058 (3)0.181 (5)0.071 (3)0.020 (3)0.024 (2)0.024 (3)
O40.053 (2)0.062 (2)0.063 (2)0.0034 (18)0.0185 (19)0.0075 (18)
O50.03753 (15)0.06274 (18)0.03704 (15)0.00008 (15)0.01023 (10)0.00146 (16)
O60.086 (3)0.067 (3)0.102 (3)0.021 (2)0.019 (2)0.003 (2)
O70.045 (2)0.078 (3)0.049 (2)0.0098 (19)0.0169 (17)0.0004 (18)
O80.040 (2)0.080 (3)0.053 (2)0.0077 (18)0.0122 (17)0.005 (2)
O90.053 (2)0.100 (3)0.076 (3)0.017 (2)0.022 (2)0.011 (2)
O100.03753 (15)0.06274 (18)0.03704 (15)0.00008 (15)0.01023 (10)0.00146 (16)
O110.047 (2)0.072 (2)0.060 (2)0.0013 (19)0.0231 (18)0.0039 (19)
O120.087 (3)0.076 (3)0.102 (3)0.009 (2)0.030 (3)0.025 (2)
N110.057 (3)0.106 (4)0.093 (4)0.003 (3)0.030 (3)0.005 (3)
C10.081 (5)0.116 (6)0.097 (5)0.014 (4)0.034 (4)0.014 (4)
C20.067 (4)0.104 (5)0.094 (5)0.006 (4)0.029 (4)0.008 (4)
C30.062 (4)0.102 (5)0.092 (5)0.003 (4)0.031 (4)0.006 (4)
C40.058 (4)0.101 (5)0.092 (5)0.001 (4)0.031 (4)0.004 (4)
C50.059 (4)0.109 (5)0.092 (5)0.005 (4)0.030 (4)0.009 (4)
C60.065 (4)0.116 (5)0.096 (5)0.003 (4)0.029 (4)0.015 (4)
C70.068 (4)0.120 (6)0.099 (5)0.001 (4)0.030 (4)0.020 (5)
C80.080 (5)0.127 (6)0.107 (5)0.008 (4)0.027 (4)0.028 (5)
C90.084 (5)0.104 (6)0.136 (6)0.006 (4)0.018 (5)0.006 (5)
C100.072 (5)0.101 (6)0.116 (6)0.013 (4)0.020 (4)0.000 (4)
C110.067 (4)0.101 (6)0.107 (5)0.012 (4)0.023 (4)0.000 (4)
C120.062 (4)0.104 (6)0.099 (5)0.009 (4)0.027 (4)0.004 (4)
C130.060 (4)0.119 (6)0.102 (5)0.003 (4)0.027 (4)0.002 (5)
C140.070 (5)0.127 (6)0.112 (6)0.009 (4)0.023 (4)0.003 (5)
C150.075 (5)0.136 (7)0.118 (6)0.014 (5)0.018 (5)0.002 (5)
C160.091 (6)0.157 (8)0.137 (7)0.008 (5)0.003 (5)0.007 (6)
Geometric parameters (Å, º) top
Ce1—O12.514 (3)N11—C121.515 (7)
Ce1—O112.572 (3)N11—C41.526 (7)
Ce1—O52.602 (3)N11—C131.527 (7)
Ce1—O82.615 (3)C1—C21.515 (7)
Ce1—O42.626 (3)C1—H1A0.9600
Ce1—O102.630 (3)C1—H1B0.9600
Ce1—O72.660 (3)C1—H1C0.9600
Ce1—O22.685 (3)C2—C31.498 (7)
Ce1—N12.686 (4)C2—H2A0.9700
Ce1—N52.705 (4)C2—H2B0.9700
Ce1—N32.761 (4)C3—C41.488 (7)
C17—N11.329 (6)C3—H3A0.9700
C17—C181.397 (6)C3—H3B0.9700
C17—H170.9300C4—H4A0.9700
C18—C191.312 (6)C4—H4B0.9700
C18—H180.9300C5—C61.498 (8)
C19—N21.357 (6)C5—H5A0.9700
C19—H190.9300C5—H5B0.9700
C20—N31.335 (6)C6—C71.487 (7)
C20—C211.357 (7)C6—H6A0.9700
C20—H200.9300C6—H6B0.9700
C21—C221.342 (7)C7—C81.446 (8)
C21—H210.9300C7—H7A0.9700
C22—N41.331 (6)C7—H7B0.9700
C22—H220.9300C8—H8A0.9600
C23—N51.329 (6)C8—H8B0.9600
C23—C241.377 (6)C8—H8C0.9600
C23—H230.9300C9—C101.447 (8)
C24—C251.339 (6)C9—H9A0.9600
C24—H240.9300C9—H9B0.9600
C25—N61.342 (6)C9—H9C0.9600
C25—H250.9300C10—C111.475 (8)
C26—N21.443 (6)C10—H10A0.9700
C26—N61.444 (6)C10—H10B0.9700
C26—N41.456 (6)C11—C121.516 (8)
C26—H260.9800C11—H11A0.9700
N1—N21.359 (5)C11—H11B0.9700
N3—N41.341 (5)C12—H12A0.9700
N5—N61.345 (5)C12—H12B0.9700
N7—O21.201 (4)C13—C141.505 (8)
N7—O31.205 (5)C13—H13A0.9700
N7—O11.286 (5)C13—H13B0.9700
N8—O51.224 (5)C14—C151.521 (8)
N8—O61.228 (5)C14—H14A0.9700
N8—O41.269 (5)C14—H14B0.9700
N9—O91.220 (5)C15—C161.493 (9)
N9—O71.253 (5)C15—H15A0.9700
N9—O81.255 (5)C15—H15B0.9700
N10—O101.222 (4)C16—H16A0.9600
N10—O121.226 (5)C16—H16B0.9600
N10—O111.262 (5)C16—H16C0.9600
N11—C51.515 (6)
O1—Ce1—O1183.17 (10)O5—N8—O6122.4 (5)
O1—Ce1—O578.93 (9)O5—N8—O4118.0 (4)
O11—Ce1—O5162.09 (10)O6—N8—O4119.3 (5)
O1—Ce1—O8109.74 (10)O5—N8—Ce158.3 (2)
O11—Ce1—O871.81 (11)O6—N8—Ce1176.5 (4)
O5—Ce1—O8113.98 (10)O4—N8—Ce159.7 (2)
O1—Ce1—O479.19 (10)O9—N9—O7121.1 (4)
O11—Ce1—O4127.54 (11)O9—N9—O8122.3 (4)
O5—Ce1—O448.25 (10)O7—N9—O8116.6 (4)
O8—Ce1—O468.69 (11)O10—N10—O12123.3 (5)
O1—Ce1—O1081.30 (9)O10—N10—O11116.1 (4)
O11—Ce1—O1047.81 (10)O12—N10—O11120.5 (4)
O5—Ce1—O10128.50 (10)N7—O1—Ce1100.7 (2)
O8—Ce1—O10117.42 (10)N7—O2—Ce194.7 (3)
O4—Ce1—O10160.44 (10)N8—O4—Ce195.6 (3)
O1—Ce1—O762.13 (10)N8—O5—Ce198.1 (3)
O11—Ce1—O764.27 (11)N9—O7—Ce196.7 (3)
O5—Ce1—O7106.17 (10)N9—O8—Ce198.8 (3)
O8—Ce1—O747.72 (10)N10—O10—Ce197.2 (3)
O4—Ce1—O763.77 (10)N10—O11—Ce198.9 (3)
O10—Ce1—O7105.46 (10)C5—N11—C12111.1 (5)
O1—Ce1—O247.78 (9)C5—N11—C4107.2 (4)
O11—Ce1—O2102.67 (10)C12—N11—C4110.8 (5)
O5—Ce1—O265.18 (9)C5—N11—C13111.8 (5)
O8—Ce1—O2157.46 (10)C12—N11—C13102.5 (5)
O4—Ce1—O2100.87 (10)C4—N11—C13113.4 (5)
O10—Ce1—O266.29 (9)C2—C1—H1A109.5
O7—Ce1—O2109.90 (10)C2—C1—H1B109.5
O1—Ce1—N1114.94 (11)H1A—C1—H1B109.5
O11—Ce1—N1114.56 (12)C2—C1—H1C109.5
O5—Ce1—N174.10 (11)H1A—C1—H1C109.5
O8—Ce1—N1135.28 (12)H1B—C1—H1C109.5
O4—Ce1—N1117.72 (11)C3—C2—C1112.6 (5)
O10—Ce1—N172.24 (11)C3—C2—H2A109.1
O7—Ce1—N1176.74 (11)C1—C2—H2A109.1
O2—Ce1—N167.16 (11)C3—C2—H2B109.1
O1—Ce1—N5146.67 (11)C1—C2—H2B109.1
O11—Ce1—N5126.33 (11)H2A—C2—H2B107.8
O5—Ce1—N570.81 (11)C4—C3—C2110.3 (5)
O8—Ce1—N571.88 (12)C4—C3—H3A109.6
O4—Ce1—N570.42 (11)C2—C3—H3A109.6
O10—Ce1—N5128.80 (11)C4—C3—H3B109.6
O7—Ce1—N5113.11 (12)C2—C3—H3B109.6
O2—Ce1—N5124.81 (11)H3A—C3—H3B108.1
N1—Ce1—N570.10 (13)C3—C4—N11116.8 (5)
O1—Ce1—N3149.74 (11)C3—C4—H4A108.1
O11—Ce1—N370.72 (12)N11—C4—H4A108.1
O5—Ce1—N3126.55 (11)C3—C4—H4B108.1
O8—Ce1—N376.94 (12)N11—C4—H4B108.1
O4—Ce1—N3128.94 (11)H4A—C4—H4B107.3
O10—Ce1—N369.96 (11)C6—C5—N11116.2 (5)
O7—Ce1—N3116.05 (12)C6—C5—H5A108.2
O2—Ce1—N3122.74 (11)N11—C5—H5A108.2
N1—Ce1—N365.59 (13)C6—C5—H5B108.2
N5—Ce1—N363.53 (13)N11—C5—H5B108.2
O1—Ce1—N877.76 (10)H5A—C5—H5B107.4
O11—Ce1—N8149.06 (11)C7—C6—C5111.7 (5)
O5—Ce1—N823.59 (9)C7—C6—H6A109.3
O8—Ce1—N891.93 (11)C5—C6—H6A109.3
O4—Ce1—N824.65 (10)C7—C6—H6B109.3
O10—Ce1—N8148.45 (11)C5—C6—H6B109.3
O7—Ce1—N885.22 (11)H6A—C6—H6B108.0
O2—Ce1—N882.17 (11)C8—C7—C6110.0 (6)
N1—Ce1—N895.63 (12)C8—C7—H7A109.7
N5—Ce1—N868.91 (12)C6—C7—H7A109.7
N3—Ce1—N8132.32 (12)C8—C7—H7B109.7
N1—C17—C18109.4 (5)C6—C7—H7B109.7
N1—C17—H17125.3H7A—C7—H7B108.2
C18—C17—H17125.3C7—C8—H8A109.5
C19—C18—C17107.6 (5)C7—C8—H8B109.5
C19—C18—H18126.2H8A—C8—H8B109.5
C17—C18—H18126.2C7—C8—H8C109.5
C18—C19—N2107.0 (5)H8A—C8—H8C109.5
C18—C19—H19126.5H8B—C8—H8C109.5
N2—C19—H19126.5C10—C9—H9A109.5
N3—C20—C21112.4 (5)C10—C9—H9B109.5
N3—C20—H20123.8H9A—C9—H9B109.5
C21—C20—H20123.8C10—C9—H9C109.5
C22—C21—C20105.5 (5)H9A—C9—H9C109.5
C22—C21—H21127.3H9B—C9—H9C109.5
C20—C21—H21127.3C9—C10—C11112.7 (6)
N4—C22—C21106.8 (5)C9—C10—H10A109.1
N4—C22—H22126.6C11—C10—H10A109.1
C21—C22—H22126.6C9—C10—H10B109.1
N5—C23—C24111.9 (5)C11—C10—H10B109.1
N5—C23—H23124.0H10A—C10—H10B107.8
C24—C23—H23124.0C10—C11—C12109.7 (6)
C25—C24—C23105.0 (5)C10—C11—H11A109.7
C25—C24—H24127.5C12—C11—H11A109.7
C23—C24—H24127.5C10—C11—H11B109.7
C24—C25—N6107.7 (5)C12—C11—H11B109.7
C24—C25—H25126.1H11A—C11—H11B108.2
N6—C25—H25126.1N11—C12—C11116.3 (5)
N2—C26—N6112.3 (4)N11—C12—H12A108.2
N2—C26—N4111.6 (4)C11—C12—H12A108.2
N6—C26—N4110.7 (4)N11—C12—H12B108.2
N2—C26—H26107.3C11—C12—H12B108.2
N6—C26—H26107.3H12A—C12—H12B107.4
N4—C26—H26107.3C14—C13—N11114.3 (5)
C17—N1—N2105.0 (4)C14—C13—H13A108.7
C17—N1—Ce1128.7 (3)N11—C13—H13A108.7
N2—N1—Ce1125.9 (3)C14—C13—H13B108.7
C19—N2—N1110.9 (4)N11—C13—H13B108.7
C19—N2—C26127.3 (4)H13A—C13—H13B107.6
N1—N2—C26121.4 (4)C13—C14—C15111.6 (6)
C20—N3—N4102.7 (4)C13—C14—H14A109.3
C20—N3—Ce1131.3 (4)C15—C14—H14A109.3
N4—N3—Ce1125.1 (3)C13—C14—H14B109.3
C22—N4—N3112.7 (5)C15—C14—H14B109.3
C22—N4—C26125.9 (5)H14A—C14—H14B108.0
N3—N4—C26121.4 (4)C16—C15—C14117.2 (7)
C23—N5—N6103.9 (4)C16—C15—H15A108.0
C23—N5—Ce1129.9 (3)C14—C15—H15A108.0
N6—N5—Ce1126.2 (3)C16—C15—H15B108.0
C25—N6—N5111.4 (4)C14—C15—H15B108.0
C25—N6—C26126.3 (5)H15A—C15—H15B107.2
N5—N6—C26121.9 (4)C15—C16—H16A109.5
O2—N7—O3124.7 (4)C15—C16—H16B109.5
O2—N7—O1116.2 (4)H16A—C16—H16B109.5
O3—N7—O1119.0 (4)C15—C16—H16C109.5
O2—N7—Ce162.0 (2)H16A—C16—H16C109.5
O3—N7—Ce1172.4 (3)H16B—C16—H16C109.5
O1—N7—Ce154.63 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4B···O9i0.972.463.421 (7)173
C5—H5B···O12ii0.972.553.445 (8)153
C13—H13A···O5iii0.972.373.311 (7)163
C19—H19···O1iv0.932.313.080 (6)140
C25—H25···O11iv0.932.493.365 (6)158
C26—H26···O7iv0.982.253.221 (6)170
Symmetry codes: (i) x+1, y1/2, z+1/2; (ii) x, y1, z; (iii) x, y1/2, z+1/2; (iv) x, y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula(C16H36N)[Ce(NO3)4(C10H10N6)]
Mr844.86
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)12.484 (1), 16.742 (1), 18.267 (1)
β (°) 102.82 (1)
V3)3722.8 (4)
Z4
Radiation typeMo Kα
µ (mm1)1.29
Crystal size (mm)0.3 × 0.2 × 0.2
Data collection
DiffractometerBruker SMART APEX CCD area-detector
diffractometer
Absorption correctionMulti-scan
(Sheldrick, 1990)
Tmin, Tmax0.740, 0.771
No. of measured, independent and
observed [I > 2σ(I)] reflections
18988, 6546, 4018
Rint0.037
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.092, 1.02
No. of reflections6546
No. of parameters431
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.67, 0.59

Computer programs: SMART (Bruker, 2000), SMART, SAINT (Bruker, 2000), SHELXTL (Bruker, 2000), SHELXTL.

Selected bond lengths (Å) top
Ce1—O12.514 (3)Ce1—O72.660 (3)
Ce1—O112.572 (3)Ce1—O22.685 (3)
Ce1—O52.602 (3)Ce1—N12.686 (4)
Ce1—O82.615 (3)Ce1—N52.705 (4)
Ce1—O42.626 (3)Ce1—N32.761 (4)
Ce1—O102.630 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4B···O9i0.972.463.421 (7)173
C5—H5B···O12ii0.972.553.445 (8)153
C13—H13A···O5iii0.972.373.311 (7)163
C19—H19···O1iv0.932.313.080 (6)140
C25—H25···O11iv0.932.493.365 (6)158
C26—H26···O7iv0.982.253.221 (6)170
Symmetry codes: (i) x+1, y1/2, z+1/2; (ii) x, y1, z; (iii) x, y1/2, z+1/2; (iv) x, y+3/2, z+1/2.
 

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