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In the title compound, [Co(C4H4O5)(C3H4N2)3], the cobalt(II) cation is located at the center of a distorted octahedron, being coordinated by three N atoms from three imidazole ligands and three O atoms from a malate ion. In the crystal structure, enantiomers are linked by pairs of bifurcated N—H...O hydrogen bonds to form racemic dimers.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803023407/na6259sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803023407/na6259Isup2.hkl
Contains datablock I

CCDC reference: 187384

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.036
  • wR factor = 0.095
  • Data-to-parameter ratio = 12.6

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for O3 - C3 = 10.35 su
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Co - O3 = 6.43 su PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C8 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... N3 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C1 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 3 N1 -CO -O1 -C1 -33.00 1.10 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 14 N5 -CO -O4 -C4 0.10 0.60 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 20 O1 -CO -N1 -C7 16.60 1.10 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 25 O1 -CO -N1 -C5 -167.00 0.90 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 37 O4 -CO -N5 -C13 37.10 0.70 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 42 O4 -CO -N5 -C11 -145.40 0.50 1.555 1.555 1.555 1.555 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C13 H16 Co N6 O5
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 12 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 7 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: SHELXTL (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Tris(1H-imidazole-κN3)(dl-malate-κ3O,O',O'')cobalt(II) top
Crystal data top
[Co(C4H4O5)(C3H4N2)3]F(000) = 812
Mr = 395.25Dx = 1.601 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 29 reflections
a = 8.482 (1) Åθ = 3.0–15.7°
b = 8.597 (1) ŵ = 1.09 mm1
c = 22.489 (4) ÅT = 296 K
β = 90.71 (1)°Prism, pink
V = 1639.8 (4) Å30.52 × 0.52 × 0.44 mm
Z = 4
Data collection top
Siemens P4
diffractometer
2392 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tubeRint = 0.012
Graphite monochromatorθmax = 25.0°, θmin = 1.8°
ω scansh = 010
Absorption correction: empirical (using intensity measurements)
(North et al., 1968)
k = 010
Tmin = 0.575, Tmax = 0.620l = 2626
3099 measured reflections3 standard reflections every 97 reflections
2890 independent reflections intensity decay: 1.4%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.095 w = 1/[σ2(Fo2) + (0.044P)2 + 1.2283P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max < 0.001
2890 reflectionsΔρmax = 0.51 e Å3
230 parametersΔρmin = 0.31 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0066 (7)
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
Co0.32679 (4)0.26070 (4)0.374365 (15)0.02972 (15)
O10.4083 (2)0.4938 (2)0.36153 (8)0.0364 (5)
O20.5402 (4)0.6662 (4)0.31193 (11)0.0749 (9)
O30.3090 (3)0.2573 (3)0.28027 (9)0.0466 (6)
O40.1014 (2)0.3521 (2)0.35443 (9)0.0389 (5)
O50.0058 (3)0.5411 (3)0.29756 (11)0.0570 (7)
N10.2348 (3)0.0327 (3)0.37980 (11)0.0386 (6)
N20.1311 (3)0.1897 (3)0.35282 (14)0.0506 (7)
H2'0.08690.25970.33100.061*
N30.3062 (3)0.3045 (3)0.46586 (10)0.0367 (6)
N40.3671 (4)0.3573 (4)0.55806 (13)0.0670 (10)
H4'0.42340.37150.58960.080*
N50.5661 (3)0.1887 (3)0.38167 (10)0.0350 (6)
N60.8238 (3)0.2014 (4)0.38020 (12)0.0463 (7)
H6'0.91720.23790.37530.056*
C10.4363 (3)0.5630 (4)0.31380 (13)0.0361 (7)
C20.3474 (4)0.5249 (5)0.25758 (14)0.0505 (9)
H2A0.29460.61830.24370.061*
H2B0.42290.49520.22760.061*
C30.2283 (4)0.3990 (4)0.26248 (13)0.0448 (8)
H30.17840.38270.22340.054*
C40.0994 (3)0.4358 (4)0.30816 (13)0.0369 (7)
C50.2366 (4)0.0666 (4)0.42733 (15)0.0468 (8)
H50.27460.04260.46520.056*
C60.1741 (4)0.2057 (4)0.41069 (17)0.0542 (9)
H60.16300.29380.43420.065*
C70.1696 (4)0.0455 (4)0.33554 (15)0.0439 (8)
H70.15260.00610.29750.053*
C80.1731 (4)0.3384 (6)0.49678 (16)0.0737 (13)
H80.07150.33950.48080.088*
C90.2109 (5)0.3701 (5)0.55384 (16)0.0718 (13)
H90.14190.39570.58410.086*
C100.4202 (4)0.3187 (4)0.50478 (15)0.0535 (9)
H100.52610.30350.49630.064*
C110.6281 (4)0.0517 (4)0.40156 (15)0.0472 (8)
H110.56930.03350.41380.057*
C120.7875 (4)0.0577 (5)0.40085 (15)0.0525 (9)
H120.85760.02040.41220.063*
C130.6895 (3)0.2756 (4)0.36887 (13)0.0414 (8)
H130.68310.37620.35380.050*
H3O0.407 (5)0.288 (5)0.2750 (19)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Co0.0284 (2)0.0353 (2)0.0254 (2)0.00135 (17)0.00314 (14)0.00104 (16)
O10.0417 (12)0.0396 (11)0.0279 (10)0.0082 (9)0.0007 (9)0.0021 (9)
O20.093 (2)0.083 (2)0.0492 (15)0.0511 (17)0.0059 (14)0.0030 (14)
O30.0597 (14)0.0461 (13)0.0337 (11)0.0125 (12)0.0030 (10)0.0008 (10)
O40.0294 (10)0.0490 (13)0.0381 (12)0.0014 (9)0.0042 (9)0.0039 (10)
O50.0552 (15)0.0479 (14)0.0673 (16)0.0080 (12)0.0240 (12)0.0017 (12)
N10.0344 (13)0.0393 (14)0.0419 (15)0.0033 (11)0.0066 (11)0.0005 (12)
N20.0445 (16)0.0390 (15)0.068 (2)0.0057 (13)0.0051 (14)0.0083 (14)
N30.0407 (14)0.0412 (14)0.0280 (12)0.0088 (11)0.0034 (10)0.0003 (11)
N40.093 (3)0.069 (2)0.0389 (17)0.0145 (19)0.0282 (16)0.0185 (15)
N50.0295 (13)0.0409 (14)0.0346 (13)0.0011 (11)0.0008 (10)0.0006 (11)
N60.0281 (13)0.0636 (18)0.0471 (15)0.0031 (13)0.0009 (11)0.0055 (14)
C10.0348 (16)0.0378 (16)0.0358 (16)0.0038 (13)0.0039 (12)0.0008 (13)
C20.0489 (19)0.071 (2)0.0310 (16)0.0059 (18)0.0002 (14)0.0050 (16)
C30.0483 (19)0.058 (2)0.0283 (15)0.0076 (16)0.0045 (13)0.0049 (14)
C40.0329 (15)0.0413 (17)0.0361 (16)0.0075 (14)0.0109 (12)0.0065 (14)
C50.0462 (19)0.050 (2)0.0440 (19)0.0037 (16)0.0064 (15)0.0079 (15)
C60.050 (2)0.043 (2)0.070 (2)0.0044 (16)0.0021 (18)0.0124 (17)
C70.0442 (18)0.0390 (18)0.0483 (19)0.0016 (14)0.0067 (15)0.0037 (14)
C80.043 (2)0.134 (4)0.045 (2)0.026 (2)0.0060 (16)0.030 (2)
C90.083 (3)0.096 (3)0.037 (2)0.031 (3)0.0153 (19)0.020 (2)
C100.057 (2)0.058 (2)0.0449 (19)0.0126 (18)0.0190 (16)0.0177 (17)
C110.0378 (17)0.053 (2)0.051 (2)0.0025 (15)0.0042 (15)0.0162 (16)
C120.0379 (18)0.066 (2)0.053 (2)0.0123 (17)0.0012 (15)0.0133 (18)
C130.0361 (17)0.0460 (19)0.0420 (17)0.0028 (14)0.0004 (13)0.0042 (14)
Geometric parameters (Å, º) top
Co—N32.101 (2)N5—C111.363 (4)
Co—O42.110 (2)N6—C131.327 (4)
Co—N12.114 (3)N6—C121.357 (5)
Co—O32.120 (2)N6—H6'0.8600
Co—N52.127 (2)C1—C21.500 (4)
Co—O12.141 (2)C2—C31.485 (5)
O1—C11.252 (3)C2—H2A0.9700
O2—C11.252 (4)C2—H2B0.9700
O3—C31.451 (4)C3—C41.543 (4)
O3—H3O0.88 (4)C3—H30.9800
O4—C41.265 (4)C5—C61.358 (5)
O5—C41.225 (4)C5—H50.9300
N1—C71.317 (4)C6—H60.9300
N1—C51.368 (4)C7—H70.9300
N2—C71.340 (4)C8—C91.346 (5)
N2—C61.354 (5)C8—H80.9300
N2—H2'0.8600C9—H90.9300
N3—C101.302 (4)C10—H100.9300
N3—C81.365 (4)C11—C121.354 (5)
N4—C101.327 (5)C11—H110.9300
N4—C91.332 (5)C12—H120.9300
N4—H4'0.8600C13—H130.9300
N5—C131.321 (4)
N3—Co—O493.18 (9)C3—C2—H2A108.4
N3—Co—N194.26 (10)C1—C2—H2A108.4
O4—Co—N191.33 (9)C3—C2—H2B108.4
N3—Co—O3166.98 (9)C1—C2—H2B108.4
O4—Co—O374.92 (9)H2A—C2—H2B107.4
N1—Co—O391.33 (9)O3—C3—C2108.2 (3)
N3—Co—N593.85 (9)O3—C3—C4108.9 (2)
O4—Co—N5170.50 (9)C2—C3—C4112.9 (3)
N1—Co—N594.50 (10)O3—C3—H3108.9
O3—Co—N597.43 (9)C2—C3—H3108.9
N3—Co—O189.73 (8)C4—C3—H3108.9
O4—Co—O185.21 (8)O5—C4—O4125.6 (3)
N1—Co—O1174.87 (8)O5—C4—C3119.0 (3)
O3—Co—O184.11 (8)O4—C4—C3115.4 (3)
N5—Co—O188.45 (9)C6—C5—N1109.5 (3)
C1—O1—Co128.69 (19)C6—C5—H5125.3
C3—O3—Co106.93 (17)N1—C5—H5125.3
C3—O3—H3O99 (3)N2—C6—C5106.0 (3)
Co—O3—H3O94 (3)N2—C6—H6127.0
C4—O4—Co112.92 (18)C5—C6—H6127.0
C7—N1—C5105.8 (3)N1—C7—N2110.8 (3)
C7—N1—Co125.6 (2)N1—C7—H7124.6
C5—N1—Co128.6 (2)N2—C7—H7124.6
C7—N2—C6108.0 (3)C9—C8—N3109.9 (3)
C7—N2—H2'126.0C9—C8—H8125.1
C6—N2—H2'126.0N3—C8—H8125.1
C10—N3—C8104.4 (3)N4—C9—C8106.0 (3)
C10—N3—Co127.3 (2)N4—C9—H9127.0
C8—N3—Co128.1 (2)C8—C9—H9127.0
C10—N4—C9107.7 (3)N3—C10—N4111.9 (3)
C10—N4—H4'126.1N3—C10—H10124.0
C9—N4—H4'126.1N4—C10—H10124.0
C13—N5—C11104.9 (3)C12—C11—N5110.1 (3)
C13—N5—Co125.2 (2)C12—C11—H11124.9
C11—N5—Co129.8 (2)N5—C11—H11124.9
C13—N6—C12107.8 (3)C11—C12—N6105.7 (3)
C13—N6—H6'126.1C11—C12—H12127.2
C12—N6—H6'126.1N6—C12—H12127.2
O2—C1—O1120.4 (3)N5—C13—N6111.5 (3)
O2—C1—C2118.3 (3)N5—C13—H13124.2
O1—C1—C2121.3 (3)N6—C13—H13124.2
C3—C2—C1115.6 (3)
N3—Co—O1—C1173.9 (2)N3—Co—N5—C1176.9 (3)
O4—Co—O1—C180.7 (2)O4—Co—N5—C11145.4 (5)
N1—Co—O1—C133.0 (11)N1—Co—N5—C1117.6 (3)
O3—Co—O1—C15.4 (2)O3—Co—N5—C11109.6 (3)
N5—Co—O1—C192.3 (2)O1—Co—N5—C11166.6 (3)
N3—Co—O3—C314.5 (5)Co—O1—C1—O2149.6 (3)
O4—Co—O3—C338.95 (18)Co—O1—C1—C230.2 (4)
N1—Co—O3—C3129.97 (19)O2—C1—C2—C3178.7 (3)
N5—Co—O3—C3135.31 (19)O1—C1—C2—C31.1 (5)
O1—Co—O3—C347.65 (19)Co—O3—C3—C285.8 (2)
N3—Co—O4—C4137.8 (2)Co—O3—C3—C437.3 (3)
N1—Co—O4—C4127.9 (2)C1—C2—C3—O361.1 (4)
O3—Co—O4—C436.8 (2)C1—C2—C3—C459.6 (4)
N5—Co—O4—C40.1 (6)Co—O4—C4—O5153.9 (2)
O1—Co—O4—C448.3 (2)Co—O4—C4—C325.7 (3)
N3—Co—N1—C7157.4 (3)O3—C3—C4—O5171.7 (3)
O4—Co—N1—C764.1 (3)C2—C3—C4—O568.0 (4)
O3—Co—N1—C710.8 (3)O3—C3—C4—O48.6 (3)
N5—Co—N1—C7108.4 (3)C2—C3—C4—O4111.6 (3)
O1—Co—N1—C716.6 (11)C7—N1—C5—C61.0 (4)
N3—Co—N1—C526.2 (3)Co—N1—C5—C6175.9 (2)
O4—Co—N1—C5119.5 (3)C7—N2—C6—C50.9 (4)
O3—Co—N1—C5165.5 (3)N1—C5—C6—N21.2 (4)
N5—Co—N1—C568.0 (3)C5—N1—C7—N20.4 (4)
O1—Co—N1—C5167.0 (9)Co—N1—C7—N2176.7 (2)
O4—Co—N3—C10158.2 (3)C6—N2—C7—N10.3 (4)
N1—Co—N3—C10110.2 (3)C10—N3—C8—C90.8 (5)
O3—Co—N3—C10134.6 (4)Co—N3—C8—C9175.4 (3)
N5—Co—N3—C1015.4 (3)C10—N4—C9—C80.1 (5)
O1—Co—N3—C1073.0 (3)N3—C8—C9—N40.6 (6)
O4—Co—N3—C815.2 (3)C8—N3—C10—N40.8 (4)
N1—Co—N3—C876.3 (3)Co—N3—C10—N4175.4 (2)
O3—Co—N3—C838.8 (6)C9—N4—C10—N30.4 (5)
N5—Co—N3—C8171.2 (3)C13—N5—C11—C120.3 (4)
O1—Co—N3—C8100.4 (3)Co—N5—C11—C12177.5 (2)
N3—Co—N5—C13100.5 (2)N5—C11—C12—N60.1 (4)
O4—Co—N5—C1337.1 (7)C13—N6—C12—C110.5 (4)
N1—Co—N5—C13164.9 (2)C11—N5—C13—N60.7 (3)
O3—Co—N5—C1372.9 (2)Co—N5—C13—N6177.34 (19)
O1—Co—N5—C1310.9 (2)C12—N6—C13—N50.7 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2A···O50.972.823.047 (4)94
C5—H5···N30.933.003.356 (4)105
C7—H7···O30.932.663.124 (4)112
C8—H8···O40.932.863.253 (4)107
C10—H10···N50.932.783.245 (4)112
C11—H11···N10.932.983.369 (4)107
C13—H13···O10.932.553.037 (4)113
C13—H13···O20.932.923.805 (5)159
N2—H2···O5i0.861.992.828 (4)165
N4—H4···O1ii0.862.132.907 (4)150
N4—H4···O2ii0.862.253.025 (4)149
N6—H6···O4iii0.861.912.755 (3)168
C2—H2B···O2iv0.972.983.591 (5)122
O3—H3O···O2iv0.88 (4)2.27 (4)2.572 (3)100 (3)
C2—H2B···N5v0.972.973.519 (4)117
C7—H7···O5vi0.932.543.409 (4)155
C11—H11···N4vii0.932.903.631 (5)136
Symmetry codes: (i) x, y1, z; (ii) x1, y+1, z1; (iii) x1, y, z; (iv) x1, y1/2, z1/2; (v) x1, y+1/2, z1/2; (vi) x, y1/2, z1/2; (vii) x1, y, z1.
 

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