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In the title compound, [Co(C4H7N2O2)2Cl(C10H10N2)], the CoIII atom has a distorted octa­hedral geometry defined by five N atoms from two dimethyl­glyoximate ligands and one 1-benzyl­imidazole group, and one chloro anion. The two dimethyl­glyoximate ligands lie trans to each other.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805011359/ng6128sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805011359/ng6128Isup2.hkl
Contains datablock I

CCDC reference: 272048

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.045
  • wR factor = 0.112
  • Data-to-parameter ratio = 15.6

checkCIF/PLATON results

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Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.33 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C15 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C13 PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2002); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

(1-Benzylimidazole)(chloro)bis(dimethylglyoximato)cobalt(III) top
Crystal data top
[Co(C4H7N2O2)2(C10H10N2)Cl]F(000) = 1000
Mr = 482.81Dx = 1.451 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2951 reflections
a = 8.1038 (7) Åθ = 1.9–28.4°
b = 21.675 (1) ŵ = 0.93 mm1
c = 12.6164 (9) ÅT = 295 K
β = 94.126 (6)°Prism, dark red
V = 2210.3 (3) Å30.37 × 0.24 × 0.15 mm
Z = 4
Data collection top
Bruker APEX area-detector
diffractometer
4332 independent reflections
Radiation source: fine-focus sealed tube2676 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.078
φ and ω scanθmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 99
Tmin = 0.753, Tmax = 0.871k = 2618
13220 measured reflectionsl = 1514
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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112H atoms treated by a mixture of independent and constrained refinement
S = 0.92 w = 1/[σ2(Fo2) + (0.0489P)2]
where P = (Fo2 + 2Fc2)/3
4332 reflections(Δ/σ)max = 0.001
277 parametersΔρmax = 0.37 e Å3
2 restraintsΔρmin = 0.30 e Å3
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
Co10.86392 (5)0.663673 (19)0.44904 (3)0.02641 (15)
Cl10.72011 (11)0.67389 (4)0.29190 (6)0.0410 (2)
O10.9728 (3)0.54541 (12)0.3838 (2)0.0497 (7)
H10.875 (2)0.545 (2)0.407 (3)0.080*
O21.0148 (3)0.78126 (11)0.42045 (19)0.0521 (7)
O30.7533 (3)0.78263 (12)0.5115 (2)0.0473 (7)
H30.849 (3)0.785 (2)0.485 (3)0.080*
O40.7084 (3)0.54649 (11)0.47617 (19)0.0497 (7)
C11.1375 (5)0.62818 (18)0.3505 (3)0.0395 (9)
C21.1491 (4)0.69586 (18)0.3601 (3)0.0397 (9)
C31.2652 (5)0.5897 (2)0.3001 (3)0.0714 (14)
H3A1.23680.54680.30510.080*
H3B1.37180.59670.33640.080*
H3C1.26840.60100.22670.080*
C41.2870 (5)0.7329 (2)0.3196 (3)0.0649 (13)
H4A1.26780.77600.33190.080*
H4B1.29180.72580.24480.080*
H4C1.38990.72080.35620.080*
C50.5941 (4)0.70013 (17)0.5521 (2)0.0340 (8)
C60.5817 (4)0.63223 (17)0.5427 (2)0.0352 (9)
C70.4687 (5)0.7385 (2)0.6037 (3)0.0583 (12)
H7A0.49930.78130.60060.080*
H7B0.46460.72630.67660.080*
H7C0.36200.73270.56700.080*
C80.4474 (5)0.5954 (2)0.5878 (3)0.0615 (12)
H8A0.46470.55240.57460.080*
H8B0.34220.60780.55470.080*
H8C0.44890.60250.66300.080*
C91.0521 (4)0.69834 (15)0.6529 (3)0.0343 (8)
H91.05900.74000.63640.080*
C101.1072 (4)0.67170 (17)0.7461 (3)0.0406 (9)
H101.15780.69160.80510.080*
C110.9989 (4)0.59974 (16)0.6392 (2)0.0357 (8)
H110.96330.56150.61300.080*
C121.0934 (5)0.56391 (18)0.8224 (3)0.0530 (11)
H12A1.19910.56980.86230.080*
H12B1.09220.52280.79180.080*
C130.9564 (6)0.56967 (18)0.8957 (3)0.0528 (11)
C140.7959 (8)0.5605 (3)0.8611 (4)0.0851 (16)
H140.77000.55060.79010.080*
C150.6688 (8)0.5656 (3)0.9294 (6)0.113 (2)
H150.55950.55920.90410.080*
C160.7063 (11)0.5802 (3)1.0344 (6)0.110 (2)
H160.62300.58361.08110.080*
C170.8663 (10)0.5897 (3)1.0688 (4)0.100 (2)
H170.89210.59981.13970.080*
C180.9918 (7)0.5846 (2)1.0014 (3)0.0741 (15)
H181.10080.59131.02700.080*
N11.0062 (4)0.60607 (13)0.38785 (19)0.0326 (7)
N21.0259 (4)0.71957 (13)0.4061 (2)0.0351 (7)
N30.7223 (3)0.72184 (12)0.51051 (19)0.0303 (6)
N40.7007 (3)0.60808 (12)0.49238 (19)0.0314 (7)
N50.9838 (3)0.65284 (11)0.58642 (18)0.0259 (6)
N61.0740 (4)0.61006 (13)0.7368 (2)0.0379 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Co10.0276 (3)0.0236 (3)0.0281 (2)0.0006 (2)0.00246 (18)0.00020 (18)
Cl10.0404 (5)0.0504 (6)0.0315 (5)0.0073 (4)0.0027 (4)0.0029 (4)
O10.0579 (19)0.0320 (15)0.0600 (17)0.0092 (14)0.0091 (14)0.0104 (12)
O20.0580 (19)0.0284 (15)0.0701 (18)0.0104 (13)0.0065 (14)0.0089 (13)
O30.0492 (18)0.0281 (15)0.0649 (18)0.0034 (13)0.0059 (14)0.0050 (12)
O40.0620 (19)0.0240 (14)0.0633 (17)0.0124 (13)0.0053 (14)0.0036 (12)
C10.034 (2)0.056 (3)0.0295 (19)0.0082 (19)0.0040 (17)0.0001 (17)
C20.026 (2)0.061 (3)0.032 (2)0.0024 (19)0.0023 (16)0.0140 (17)
C30.051 (3)0.099 (4)0.066 (3)0.020 (3)0.017 (2)0.014 (3)
C40.040 (3)0.090 (4)0.065 (3)0.011 (2)0.007 (2)0.027 (2)
C50.026 (2)0.045 (2)0.0310 (19)0.0025 (16)0.0035 (16)0.0077 (15)
C60.028 (2)0.047 (2)0.0309 (19)0.0064 (17)0.0014 (16)0.0003 (15)
C70.040 (3)0.068 (3)0.067 (3)0.008 (2)0.012 (2)0.019 (2)
C80.049 (3)0.069 (3)0.068 (3)0.019 (2)0.019 (2)0.001 (2)
C90.035 (2)0.030 (2)0.038 (2)0.0000 (16)0.0027 (16)0.0040 (15)
C100.039 (2)0.042 (2)0.040 (2)0.0030 (18)0.0018 (17)0.0089 (17)
C110.040 (2)0.033 (2)0.0333 (19)0.0036 (17)0.0004 (16)0.0026 (15)
C120.072 (3)0.051 (3)0.035 (2)0.016 (2)0.007 (2)0.0113 (18)
C130.081 (3)0.039 (2)0.037 (2)0.004 (2)0.000 (2)0.0072 (17)
C140.092 (4)0.104 (5)0.060 (3)0.001 (3)0.011 (3)0.001 (3)
C150.082 (5)0.139 (6)0.120 (5)0.006 (4)0.020 (4)0.017 (4)
C160.147 (7)0.095 (5)0.098 (5)0.023 (5)0.073 (5)0.019 (4)
C170.174 (7)0.075 (4)0.055 (3)0.011 (5)0.033 (4)0.002 (3)
C180.123 (5)0.058 (3)0.042 (3)0.001 (3)0.014 (3)0.001 (2)
N10.0387 (19)0.0298 (17)0.0293 (15)0.0051 (14)0.0027 (13)0.0001 (12)
N20.0349 (18)0.0360 (18)0.0345 (16)0.0013 (14)0.0025 (13)0.0076 (13)
N30.0326 (17)0.0242 (16)0.0338 (15)0.0008 (13)0.0009 (13)0.0014 (12)
N40.0335 (17)0.0284 (17)0.0319 (15)0.0040 (13)0.0007 (13)0.0005 (12)
N50.0289 (16)0.0246 (15)0.0245 (14)0.0014 (12)0.0037 (12)0.0016 (11)
N60.047 (2)0.0378 (19)0.0283 (16)0.0036 (15)0.0035 (14)0.0009 (13)
Geometric parameters (Å, º) top
Co1—Cl12.2373 (9)C7—H7B0.9600
Co1—N11.901 (3)C7—H7C0.9600
Co1—N21.894 (3)C8—H8A0.9600
Co1—N31.907 (3)C8—H8B0.9600
Co1—N41.899 (3)C8—H8C0.9600
Co1—N51.939 (2)C9—C101.357 (4)
O1—N11.343 (4)C9—N51.384 (4)
O1—H10.863 (10)C9—H90.9300
O2—N21.353 (3)C10—N61.366 (4)
O3—N31.341 (3)C10—H100.9300
O3—H30.87 (3)C11—N51.331 (4)
O4—N41.353 (3)C11—N61.353 (4)
C1—C21.474 (5)C11—H110.9300
C1—C31.505 (5)C12—C131.500 (5)
C1—N11.286 (4)C12—N61.472 (4)
C2—N21.297 (4)C12—H12A0.9700
C2—C41.496 (5)C12—H12B0.9700
C3—H3A0.9600C13—C141.356 (6)
C3—H3B0.9600C13—C181.383 (5)
C3—H3C0.9600C14—C151.394 (7)
C4—H4A0.9600C14—H140.9300
C4—H4B0.9600C15—C161.375 (8)
C4—H4C0.9600C15—H150.9300
C5—C61.479 (5)C16—C171.353 (8)
C5—C71.498 (5)C16—H160.9300
C5—N31.286 (4)C17—C181.376 (7)
C6—C81.494 (5)C17—H170.9300
C6—N41.302 (4)C18—H180.9300
C7—H7A0.9600
N1—Co1—N3179.63 (13)C14—C13—C18118.2 (5)
N1—Co1—N590.22 (11)C14—C13—C12121.7 (4)
N1—Co1—Cl189.87 (8)C14—C15—H15120.3
N2—Co1—N181.43 (13)C15—C14—H14119.2
N2—Co1—N398.22 (12)C16—C15—C14119.5 (6)
N2—Co1—N4179.61 (13)C16—C15—H15120.3
N2—Co1—N591.15 (11)C17—C16—C15119.0 (6)
N2—Co1—Cl190.63 (8)C17—C16—H16120.5
N3—Co1—N589.66 (10)C15—C16—H16120.5
N3—Co1—Cl190.26 (8)C16—C17—C18121.6 (6)
N4—Co1—N198.96 (12)C16—C17—H17119.2
N4—Co1—N381.39 (12)C18—C17—H17119.2
N4—Co1—N588.88 (11)C18—C13—C12120.2 (4)
N4—Co1—Cl189.35 (8)C17—C18—C13120.3 (5)
N5—Co1—Cl1178.22 (8)C17—C18—H18119.9
C1—C2—C4123.5 (4)O1—N1—Co1122.2 (2)
C1—C3—H3A109.5O2—N2—Co1122.7 (2)
C1—C3—H3B109.5O3—N3—Co1122.4 (2)
C1—C3—H3C109.5O4—N4—Co1122.8 (2)
C1—N1—O1121.4 (3)C5—N3—O3120.8 (3)
C1—N1—Co1116.5 (2)C5—N3—Co1116.8 (2)
C2—C1—C3123.0 (4)N1—C1—C2113.0 (3)
C2—C4—H4A109.5N1—C1—C3124.0 (4)
C2—C4—H4B109.5N1—O1—H1101 (3)
C2—C4—H4C109.5N2—C2—C1112.6 (3)
C2—N2—O2120.8 (3)N2—C2—C4123.9 (4)
C2—N2—Co1116.5 (3)N3—C5—C6112.5 (3)
C5—C6—C8123.2 (3)N3—C5—C7124.5 (3)
C5—C7—H7A109.5N3—O3—H3104 (3)
C5—C7—H7B109.5N4—C6—C5113.0 (3)
C5—C7—H7C109.5N4—C6—C8123.8 (3)
C6—C5—C7122.9 (3)N5—C9—H9125.8
C6—C8—H8A109.5N5—C11—N6109.4 (3)
C6—C8—H8B109.5N5—C11—H11125.3
C6—C8—H8C109.5N6—C10—H10126.5
C6—N4—O4121.0 (3)N6—C11—H11125.3
C6—N4—Co1116.2 (2)N6—C12—C13110.5 (3)
C9—C10—N6106.9 (3)N6—C12—H12A109.5
C9—C10—H10126.5N6—C12—H12B109.5
C9—N5—Co1127.4 (2)H3A—C3—H3B109.5
C10—C9—N5108.3 (3)H3A—C3—H3C109.5
C10—C9—H9125.8H3B—C3—H3C109.5
C10—N6—C12126.3 (3)H4A—C4—H4B109.5
C11—N5—C9107.2 (3)H4A—C4—H4C109.5
C11—N5—Co1125.0 (2)H4B—C4—H4C109.5
C11—N6—C10108.2 (3)H7A—C7—H7B109.5
C11—N6—C12125.0 (3)H7A—C7—H7C109.5
C13—C12—H12A109.5H7B—C7—H7C109.5
C13—C12—H12B109.5H8A—C8—H8B109.5
C13—C14—C15121.6 (5)H8A—C8—H8C109.5
C13—C14—H14119.2H8B—C8—H8C109.5
C13—C18—H18119.9H12A—C12—H12B108.1
C1—C2—N2—O2179.1 (2)N2—Co1—N1—O1178.9 (2)
C1—C2—N2—Co10.0 (4)N2—Co1—N3—C5178.6 (2)
C2—C1—N1—O1178.5 (3)N2—Co1—N3—O31.1 (2)
C2—C1—N1—Co11.7 (4)N2—Co1—N5—C11141.9 (3)
C3—C1—N1—O10.4 (5)N2—Co1—N5—C946.1 (3)
C3—C1—N1—Co1179.4 (3)N3—C5—C6—N41.3 (4)
C3—C1—C2—N2180.0 (3)N3—C5—C6—C8177.9 (3)
C3—C1—C2—C40.9 (5)N3—Co1—N2—C2179.2 (2)
C4—C2—N2—O20.1 (5)N3—Co1—N2—O21.8 (2)
C4—C2—N2—Co1179.1 (3)N3—Co1—N4—C62.2 (2)
C5—C6—N4—O4179.8 (2)N3—Co1—N4—O4179.9 (2)
C5—C6—N4—Co12.5 (3)N3—Co1—N5—C11119.9 (3)
C6—C5—N3—O3179.9 (3)N3—Co1—N5—C952.1 (3)
C6—C5—N3—Co10.5 (3)N4—Co1—N1—C1178.7 (2)
C7—C5—C6—N4178.0 (3)N4—Co1—N1—O11.1 (2)
C7—C5—C6—C82.8 (5)N4—Co1—N3—C51.4 (2)
C7—C5—N3—O30.5 (5)N4—Co1—N3—O3178.9 (2)
C7—C5—N3—Co1179.8 (3)N4—Co1—N5—C1138.5 (3)
C8—C6—N4—Co1176.7 (3)N4—Co1—N5—C9133.5 (3)
C8—C6—N4—O41.0 (5)N5—C9—C10—N60.4 (4)
C9—C10—N6—C110.3 (4)N5—Co1—N1—C189.8 (2)
C9—C10—N6—C12172.1 (3)N5—Co1—N1—O190.0 (2)
C10—C9—N5—C110.3 (4)N5—Co1—N2—C289.4 (2)
C10—C9—N5—Co1172.8 (2)N5—Co1—N2—O291.6 (2)
C12—C13—C14—C15179.7 (5)N5—Co1—N3—C587.5 (2)
C12—C13—C18—C17179.7 (4)N5—Co1—N3—O392.2 (2)
C13—C14—C15—C160.1 (10)N5—Co1—N4—C687.6 (2)
C13—C12—N6—C1195.2 (4)N5—Co1—N4—O490.0 (2)
C13—C12—N6—C1075.3 (5)N5—C11—N6—C100.1 (4)
C14—C15—C16—C170.4 (10)N5—C11—N6—C12172.0 (3)
C14—C13—C18—C170.3 (7)N6—C12—C13—C1462.4 (5)
C15—C16—C17—C180.3 (10)N6—C12—C13—C18117.7 (4)
C16—C17—C18—C130.0 (9)N6—C11—N5—C90.1 (4)
C18—C13—C14—C150.3 (8)N6—C11—N5—Co1173.2 (2)
N1—C1—C2—N21.1 (4)Cl1—Co1—N1—C192.0 (2)
N1—C1—C2—C4178.0 (3)Cl1—Co1—N1—O188.2 (2)
N1—Co1—N2—C20.6 (2)Cl1—Co1—N2—C290.4 (2)
N1—Co1—N2—O2178.4 (2)Cl1—Co1—N2—O288.6 (2)
N1—Co1—N4—C6177.6 (2)Cl1—Co1—N3—C590.7 (2)
N1—Co1—N4—O40.0 (2)Cl1—Co1—N3—O389.6 (2)
N1—Co1—N5—C1160.5 (3)Cl1—Co1—N4—C692.6 (2)
N1—Co1—N5—C9127.6 (3)Cl1—Co1—N4—O489.8 (2)
N2—Co1—N1—C11.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O40.86 (1)1.66 (1)2.512 (4)168 (4)
O1—H1···N40.86 (1)2.29 (3)3.004 (4)140 (4)
O3—H3···O20.87 (3)1.62 (3)2.482 (4)170 (5)
O3—H3···N20.87 (3)2.30 (3)2.989 (4)137 (4)
 

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