Literature DB >> 22719390

Bis{2-[bis-(3,5-dimethyl-1H-pyrazol-1-yl-κN(2))meth-yl]pyridine-κN}cobalt(II) dinitrate.

Chao-Hu Xiao1, Xue-Yan Song, Zan Sun, Ping Cao, Ting Pang.   

Abstract

The central Co(II) ion in the title complex, [Co(C(16)H(19)N(5))(2)](NO(3))(2), is located on a twofold rotation axis and has a slightly distorted octa-hedral coordination sphere. It is bonded to six N atoms from two 2-[bis-(3,5-dimethyl-1H-pyrazol-1-yl)meth-yl]pyridine ligands. In the crystal, mol-ecules are linked by weak C-H⋯O inter-actions.

Entities:  

Year:  2012        PMID： 22719390      PMCID： PMC3379192          DOI： 10.1107/S1600536812021435

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For potential applications of similar rigid ligands in electrochemistry, see: Morin et al. (2011 ▶), in catalysis, see: Zhang et al. (2009 ▶), and for their fluxional behaviour, see: Otten et al. (2009 ▶); Arroyo et al. (2000 ▶). For N-heterocyclic rigid scorpion-type ligands, see: Reger et al. (2005 ▶); Liu et al. (2011 ▶).

Experimental

Crystal data

[Co(C16H19N5)2](NO3)2 M = 745.67 Monoclinic, a = 17.700 (14) Å b = 10.965 (9) Å c = 18.37 (2) Å β = 90.431 (6)° V = 3565 (6) Å3 Z = 4 Mo Kα radiation μ = 0.54 mm−1 T = 296 K 0.40 × 0.36 × 0.32 mm

Data collection

Bruker APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.805, T max = 0.841 8860 measured reflections 3297 independent reflections 2334 reflections with I > 2σ(I) R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.043 wR(F 2) = 0.131 S = 1.10 3297 reflections 235 parameters H-atom parameters constrained Δρmax = 0.46 e Å−3 Δρmin = −0.40 e Å−3 Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812021435/su2416sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812021435/su2416Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Co(C16H19N5)2](NO3)2F(000) = 1556
Mr = 745.67Dx = 1.389 Mg m−3
Monoclinic, I2/aMo Kα radiation, λ = 0.71073 Å
Hall symbol: -I 2yaCell parameters from 3198 reflections
a = 17.700 (14) Åθ = 3.1–25.0°
b = 10.965 (9) ŵ = 0.54 mm−1
c = 18.37 (2) ÅT = 296 K
β = 90.431 (6)°Block, yellow
V = 3565 (6) Å30.40 × 0.36 × 0.32 mm
Z = 4
Bruker APEXII CCD diffractometer3297 independent reflections
Radiation source: fine-focus sealed tube2334 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
φ and ω scansθmax = 25.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)h = −21→20
Tmin = 0.805, Tmax = 0.841k = −13→13
8860 measured reflectionsl = −22→14
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) = 0.131H-atom parameters constrained
S = 1.10w = 1/[σ2(Fo2) + (0.048P)2 + 5.1694P] where P = (Fo2 + 2Fc2)/3
3297 reflections(Δ/σ)max < 0.001
235 parametersΔρmax = 0.46 e Å−3
0 restraintsΔρmin = −0.40 e Å−3
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles
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.
xyzUiso*/Ueq
Co10.250000.48144 (5)0.500000.0385 (2)
N10.30500 (13)0.4768 (2)0.39615 (13)0.0435 (8)
N20.25949 (14)0.4837 (2)0.33569 (13)0.0437 (8)
N30.17509 (14)0.6129 (2)0.45372 (14)0.0471 (9)
N40.15529 (14)0.5976 (2)0.38206 (14)0.0440 (9)
N50.17558 (14)0.3508 (2)0.45023 (13)0.0408 (8)
C10.37561 (18)0.4765 (3)0.37070 (18)0.0493 (11)
C20.3744 (2)0.4835 (3)0.2951 (2)0.0619 (14)
C30.3009 (2)0.4882 (3)0.27378 (18)0.0570 (11)
C40.4428 (2)0.4700 (4)0.4198 (2)0.0730 (15)
C50.2655 (3)0.4970 (5)0.1993 (2)0.098 (2)
C60.14640 (19)0.7205 (3)0.4735 (2)0.0584 (14)
C70.1088 (2)0.7730 (3)0.4140 (3)0.0724 (16)
C80.11550 (19)0.6944 (3)0.3566 (2)0.0604 (14)
C90.1552 (3)0.7711 (4)0.5482 (2)0.0830 (17)
C100.0875 (3)0.7046 (4)0.2799 (3)0.096 (2)
C110.1499 (2)0.2504 (3)0.48366 (18)0.0521 (11)
C120.0989 (2)0.1722 (3)0.4522 (2)0.0626 (14)
C130.0733 (2)0.1950 (3)0.3826 (2)0.0647 (14)
C140.09957 (19)0.2970 (3)0.34717 (18)0.0532 (11)
C150.14991 (16)0.3725 (3)0.38241 (15)0.0378 (9)
C160.17815 (17)0.4864 (3)0.34485 (16)0.0411 (9)
O10.9501 (3)0.9744 (3)0.40558 (19)0.1213 (19)
O20.8920 (2)0.8352 (4)0.3465 (2)0.137 (2)
O30.9660 (2)0.9549 (3)0.29408 (17)0.1124 (15)
N60.93398 (18)0.9236 (3)0.34876 (17)0.0573 (11)
H20.416200.484700.264700.0740*
H4A0.428600.493400.468200.1090*
H4B0.481200.524300.402500.1090*
H4C0.462000.388100.420500.1090*
H5A0.236100.425100.189800.1460*
H5B0.304400.504000.163400.1460*
H5C0.233400.567500.197000.1460*
H70.083900.847600.413600.0870*
H9A0.169300.706900.581200.1250*
H9B0.108300.806400.563400.1250*
H9C0.193800.832600.548300.1250*
H10A0.129700.713000.247700.1430*
H10B0.055300.774700.275400.1430*
H10C0.059500.632600.267300.1430*
H110.167600.233200.530300.0630*
H120.081800.104400.477600.0750*
H130.039000.142800.360000.0770*
H140.083500.314600.300000.0640*
H160.155300.488200.296100.0490*
U11U22U33U12U13U23
Co10.0381 (3)0.0442 (3)0.0330 (3)0.0000−0.0040 (2)0.0000
N10.0362 (14)0.0570 (16)0.0372 (14)−0.0025 (11)−0.0030 (11)0.0051 (12)
N20.0422 (14)0.0556 (16)0.0332 (14)−0.0038 (12)−0.0014 (11)0.0093 (12)
N30.0456 (15)0.0466 (16)0.0491 (17)0.0057 (12)−0.0076 (12)−0.0009 (12)
N40.0404 (14)0.0433 (15)0.0480 (16)−0.0011 (11)−0.0096 (12)0.0079 (12)
N50.0487 (15)0.0442 (15)0.0296 (13)−0.0063 (11)−0.0017 (11)0.0055 (11)
C10.0429 (18)0.0565 (19)0.0487 (19)0.0004 (15)0.0063 (15)0.0060 (16)
C20.054 (2)0.080 (3)0.052 (2)0.0016 (18)0.0191 (17)0.0083 (18)
C30.065 (2)0.068 (2)0.0382 (18)−0.0038 (18)0.0082 (16)0.0114 (16)
C40.0379 (19)0.102 (3)0.079 (3)0.0016 (19)−0.0014 (18)0.005 (2)
C50.097 (3)0.159 (5)0.037 (2)0.004 (3)0.005 (2)0.020 (3)
C60.051 (2)0.047 (2)0.077 (3)0.0039 (16)−0.0050 (18)−0.0030 (18)
C70.054 (2)0.042 (2)0.121 (4)0.0073 (16)−0.016 (2)0.010 (2)
C80.050 (2)0.047 (2)0.084 (3)−0.0003 (16)−0.0178 (19)0.0205 (19)
C90.092 (3)0.063 (3)0.094 (3)0.020 (2)−0.003 (3)−0.023 (2)
C100.108 (4)0.077 (3)0.101 (4)0.005 (3)−0.052 (3)0.031 (3)
C110.071 (2)0.0503 (19)0.0351 (18)−0.0071 (17)0.0008 (16)0.0088 (15)
C120.081 (3)0.052 (2)0.055 (2)−0.0218 (19)0.0063 (19)0.0017 (17)
C130.076 (3)0.061 (2)0.057 (2)−0.0229 (19)−0.004 (2)−0.0063 (18)
C140.057 (2)0.060 (2)0.0425 (19)−0.0131 (17)−0.0052 (16)−0.0012 (16)
C150.0388 (16)0.0419 (16)0.0326 (16)−0.0018 (12)−0.0008 (13)0.0026 (13)
C160.0446 (17)0.0462 (17)0.0324 (15)−0.0060 (13)−0.0084 (13)0.0086 (13)
O10.212 (5)0.093 (2)0.059 (2)−0.021 (3)0.018 (2)−0.0085 (18)
O20.152 (4)0.151 (4)0.107 (3)−0.085 (3)0.006 (3)0.013 (3)
O30.151 (3)0.129 (3)0.0576 (19)−0.058 (3)0.021 (2)0.0059 (19)
N60.069 (2)0.0579 (18)0.0448 (19)0.0007 (16)−0.0044 (15)0.0120 (15)
Co1—N12.149 (3)C8—C101.494 (7)
Co1—N32.131 (3)C11—C121.370 (5)
Co1—N52.146 (3)C12—C131.376 (5)
Co1—N1i2.149 (3)C13—C141.377 (5)
Co1—N3i2.131 (3)C14—C151.375 (5)
Co1—N5i2.146 (3)C15—C161.514 (5)
O1—N61.215 (5)C2—H20.9300
O2—N61.222 (5)C4—H4A0.9600
O3—N61.207 (5)C4—H4B0.9600
N1—N21.369 (4)C4—H4C0.9600
N1—C11.338 (4)C5—H5C0.9600
N2—C31.359 (4)C5—H5A0.9600
N2—C161.451 (4)C5—H5B0.9600
N3—N41.370 (4)C7—H70.9300
N3—C61.336 (4)C9—H9A0.9600
N4—C161.457 (4)C9—H9B0.9600
N4—C81.355 (4)C9—H9C0.9600
N5—C111.342 (4)C10—H10A0.9600
N5—C151.344 (4)C10—H10B0.9600
C1—C21.391 (5)C10—H10C0.9600
C1—C41.489 (5)C11—H110.9300
C2—C31.357 (5)C12—H120.9300
C3—C51.504 (5)C13—H130.9300
C6—C71.399 (6)C14—H140.9300
C6—C91.487 (5)C16—H160.9800
C7—C81.368 (6)
N1—Co1—N386.93 (9)C11—C12—C13119.3 (3)
N1—Co1—N583.49 (9)C12—C13—C14118.5 (3)
N1—Co1—N1i177.29 (9)C13—C14—C15119.1 (3)
N1—Co1—N3i94.91 (9)C14—C15—C16119.8 (3)
N1—Co1—N5i94.69 (9)N5—C15—C16117.3 (3)
N3—Co1—N584.46 (9)N5—C15—C14122.9 (3)
N1i—Co1—N394.91 (9)N2—C16—N4110.5 (2)
N3—Co1—N3i94.88 (9)N2—C16—C15111.6 (2)
N3—Co1—N5i178.29 (9)N4—C16—C15112.5 (2)
N1i—Co1—N594.69 (9)C1—C2—H2126.00
N3i—Co1—N5178.29 (9)C3—C2—H2126.00
N5—Co1—N5i96.25 (9)C1—C4—H4C110.00
N1i—Co1—N3i86.93 (9)H4A—C4—H4C109.00
N1i—Co1—N5i83.49 (9)H4B—C4—H4C109.00
N3i—Co1—N5i84.46 (9)H4A—C4—H4B109.00
Co1—N1—N2116.82 (17)C1—C4—H4A110.00
Co1—N1—C1137.8 (2)C1—C4—H4B110.00
N2—N1—C1105.2 (2)H5A—C5—H5B109.00
N1—N2—C3111.3 (2)H5A—C5—H5C109.00
N1—N2—C16119.0 (2)H5B—C5—H5C109.00
C3—N2—C16129.7 (3)C3—C5—H5A110.00
Co1—N3—N4117.03 (17)C3—C5—H5B110.00
Co1—N3—C6136.5 (2)C3—C5—H5C110.00
N4—N3—C6105.9 (2)C6—C7—H7126.00
N3—N4—C8111.4 (2)C8—C7—H7126.00
N3—N4—C16118.9 (2)C6—C9—H9A109.00
C8—N4—C16129.7 (3)H9A—C9—H9C109.00
Co1—N5—C11124.2 (2)H9B—C9—H9C109.00
Co1—N5—C15118.61 (19)C6—C9—H9C109.00
C11—N5—C15117.1 (3)H9A—C9—H9B109.00
O1—N6—O2122.1 (4)C6—C9—H9B110.00
O1—N6—O3118.4 (4)C8—C10—H10A110.00
O2—N6—O3119.1 (3)C8—C10—H10B109.00
C2—C1—C4127.9 (3)H10B—C10—H10C109.00
N1—C1—C4122.2 (3)H10A—C10—H10C109.00
N1—C1—C2110.0 (3)C8—C10—H10C109.00
C1—C2—C3107.3 (3)H10A—C10—H10B110.00
C2—C3—C5131.1 (4)N5—C11—H11118.00
N2—C3—C5122.7 (3)C12—C11—H11119.00
N2—C3—C2106.2 (3)C11—C12—H12120.00
N3—C6—C7109.3 (3)C13—C12—H12120.00
N3—C6—C9122.9 (3)C12—C13—H13121.00
C7—C6—C9127.8 (3)C14—C13—H13121.00
C6—C7—C8107.4 (3)C15—C14—H14120.00
C7—C8—C10130.5 (3)C13—C14—H14120.00
N4—C8—C7106.0 (3)N2—C16—H16107.00
N4—C8—C10123.5 (3)N4—C16—H16107.00
N5—C11—C12123.0 (3)C15—C16—H16107.00
N3—Co1—N1—N2−38.51 (18)C6—N3—N4—C80.7 (3)
N3—Co1—N1—C1136.0 (3)N4—N3—C6—C7−0.3 (3)
N5—Co1—N1—N246.26 (18)Co1—N3—C6—C9−9.4 (5)
N5—Co1—N1—C1−139.3 (3)C6—N3—N4—C16−179.3 (3)
N3i—Co1—N1—N2−133.15 (18)Co1—N3—N4—C8−172.3 (2)
N3i—Co1—N1—C141.3 (3)Co1—N3—C6—C7170.7 (2)
N5i—Co1—N1—N2142.02 (18)Co1—N3—N4—C167.7 (3)
N5i—Co1—N1—C1−43.5 (3)N4—N3—C6—C9179.7 (3)
N1—Co1—N3—N436.26 (19)C8—N4—C16—C15−122.9 (3)
N1—Co1—N3—C6−133.9 (3)N3—N4—C8—C10178.8 (3)
N5—Co1—N3—N4−47.50 (19)N3—N4—C16—N2−68.3 (3)
N5—Co1—N3—C6142.3 (3)N3—N4—C8—C7−0.9 (4)
N1i—Co1—N3—N4−141.75 (19)C16—N4—C8—C7179.2 (3)
N1i—Co1—N3—C648.1 (3)N3—N4—C16—C1557.1 (3)
N3i—Co1—N3—N4130.92 (19)C8—N4—C16—N2111.6 (3)
N3i—Co1—N3—C6−39.3 (3)C16—N4—C8—C10−1.1 (5)
N1—Co1—N5—C11137.7 (3)C11—N5—C15—C16179.4 (3)
N1—Co1—N5—C15−45.4 (2)Co1—N5—C15—C162.3 (3)
N3—Co1—N5—C11−134.8 (3)C15—N5—C11—C12−0.9 (5)
N3—Co1—N5—C1542.1 (2)C11—N5—C15—C14−0.1 (4)
N1i—Co1—N5—C11−40.3 (3)Co1—N5—C15—C14−177.2 (2)
N1i—Co1—N5—C15136.6 (2)Co1—N5—C11—C12176.0 (3)
N5i—Co1—N5—C1143.7 (3)C4—C1—C2—C3−179.7 (4)
N5i—Co1—N5—C15−139.5 (2)N1—C1—C2—C30.0 (4)
Co1—N1—N2—C3175.87 (19)C1—C2—C3—N2−0.2 (4)
Co1—N1—N2—C16−3.6 (3)C1—C2—C3—C5179.7 (4)
C1—N1—N2—C3−0.3 (3)N3—C6—C7—C8−0.3 (4)
C1—N1—N2—C16−179.7 (3)C9—C6—C7—C8179.8 (4)
N2—N1—C1—C4179.9 (3)C6—C7—C8—C10−179.0 (4)
Co1—N1—C1—C2−174.7 (2)C6—C7—C8—N40.7 (4)
N2—N1—C1—C20.2 (3)N5—C11—C12—C131.3 (5)
Co1—N1—C1—C45.0 (5)C11—C12—C13—C14−0.6 (5)
C3—N2—C16—C15120.1 (3)C12—C13—C14—C15−0.3 (5)
N1—N2—C16—C15−60.6 (3)C13—C14—C15—C16−178.8 (3)
N1—N2—C3—C20.3 (3)C13—C14—C15—N50.7 (5)
C16—N2—C3—C5−0.2 (5)N5—C15—C16—N261.6 (3)
N1—N2—C3—C5−179.6 (3)C14—C15—C16—N2−119.0 (3)
C3—N2—C16—N4−113.9 (3)C14—C15—C16—N4116.2 (3)
C16—N2—C3—C2179.6 (3)N5—C15—C16—N4−63.3 (3)
N1—N2—C16—N465.4 (3)
D—H···AD—HH···AD···AD—H···A
C2—H2···O3ii0.932.453.345 (6)162
C5—H5A···O2iii0.962.563.405 (7)147
C10—H10B···O3iv0.962.563.498 (7)167
C10—H10C···O3iii0.962.293.197 (7)156
C12—H12···O1v0.932.393.193 (6)145
C13—H13···O1vi0.932.573.286 (7)134
C14—H14···O3iii0.932.473.322 (6)152
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C2—H2⋯O3i0.932.453.345 (6)162
C5—H5A⋯O2ii0.962.563.405 (7)147
C10—H10B⋯O3iii0.962.563.498 (7)167
C10—H10C⋯O3ii0.962.293.197 (7)156
C12—H12⋯O1iv0.932.393.193 (6)145
C13—H13⋯O1v0.932.573.286 (7)134
C14—H14⋯O3ii0.932.473.322 (6)152

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .

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5.  Bis{2-[bis-(3,5-dimethyl-1H-pyrazol-1-yl-κN)meth-yl]pyridine-κN}copper(II) dinitrate.

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