Tris(1H-imidazole-κN³)(DL-malato-κ³O,O′,O′′)­cobalt(II)

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.

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

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Computing details

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)

Crystal data

[Co(C4H4O5)(C3H4N2)3]	F(000) = 812
Mr = 395.25	Dx = 1.601 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 29 reflections
a = 8.482 (1) Å	θ = 3.0–15.7°
b = 8.597 (1) Å	µ = 1.09 mm^−1
c = 22.489 (4) Å	T = 296 K
β = 90.71 (1)°	Prism, pink
V = 1639.8 (4) Å^3	0.52 × 0.52 × 0.44 mm
Z = 4

Data collection

Siemens P4 diffractometer	2392 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tube	Rint = 0.012
Graphite monochromator	θmax = 25.0°, θmin = 1.8°
ω scans	h = 0→10
Absorption correction: empirical (using intensity measurements) (North et al., 1968)	k = 0→10
Tmin = 0.575, Tmax = 0.620	l = −26→26
3099 measured reflections	3 standard reflections every 97 reflections
2890 independent reflections	intensity decay: 1.4%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.095	w = 1/[σ^2(Fo^2) + (0.044P)^2 + 1.2283P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max < 0.001
2890 reflections	Δρmax = 0.51 e Å^−3
230 parameters	Δρmin = −0.31 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0066 (7)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Co	−0.32679 (4)	0.26070 (4)	−0.374365 (15)	0.02972 (15)
O1	−0.4083 (2)	0.4938 (2)	−0.36153 (8)	0.0364 (5)
O2	−0.5402 (4)	0.6662 (4)	−0.31193 (11)	0.0749 (9)
O3	−0.3090 (3)	0.2573 (3)	−0.28027 (9)	0.0466 (6)
O4	−0.1014 (2)	0.3521 (2)	−0.35443 (9)	0.0389 (5)
O5	−0.0058 (3)	0.5411 (3)	−0.29756 (11)	0.0570 (7)
N1	−0.2348 (3)	0.0327 (3)	−0.37980 (11)	0.0386 (6)
N2	−0.1311 (3)	−0.1897 (3)	−0.35282 (14)	0.0506 (7)
H2'	−0.0869	−0.2597	−0.3310	0.061*
N3	−0.3062 (3)	0.3045 (3)	−0.46586 (10)	0.0367 (6)
N4	−0.3671 (4)	0.3573 (4)	−0.55806 (13)	0.0670 (10)
H4'	−0.4234	0.3715	−0.5896	0.080*
N5	−0.5661 (3)	0.1887 (3)	−0.38167 (10)	0.0350 (6)
N6	−0.8238 (3)	0.2014 (4)	−0.38020 (12)	0.0463 (7)
H6'	−0.9172	0.2379	−0.3753	0.056*
C1	−0.4363 (3)	0.5630 (4)	−0.31380 (13)	0.0361 (7)
C2	−0.3474 (4)	0.5249 (5)	−0.25758 (14)	0.0505 (9)
H2A	−0.2946	0.6183	−0.2437	0.061*
H2B	−0.4229	0.4952	−0.2276	0.061*
C3	−0.2283 (4)	0.3990 (4)	−0.26248 (13)	0.0448 (8)
H3	−0.1784	0.3827	−0.2234	0.054*
C4	−0.0994 (3)	0.4358 (4)	−0.30816 (13)	0.0369 (7)
C5	−0.2366 (4)	−0.0666 (4)	−0.42733 (15)	0.0468 (8)
H5	−0.2746	−0.0426	−0.4652	0.056*
C6	−0.1741 (4)	−0.2057 (4)	−0.41069 (17)	0.0542 (9)
H6	−0.1630	−0.2938	−0.4342	0.065*
C7	−0.1696 (4)	−0.0455 (4)	−0.33554 (15)	0.0439 (8)
H7	−0.1526	−0.0061	−0.2975	0.053*
C8	−0.1731 (4)	0.3384 (6)	−0.49678 (16)	0.0737 (13)
H8	−0.0715	0.3395	−0.4808	0.088*
C9	−0.2109 (5)	0.3701 (5)	−0.55384 (16)	0.0718 (13)
H9	−0.1419	0.3957	−0.5841	0.086*
C10	−0.4202 (4)	0.3187 (4)	−0.50478 (15)	0.0535 (9)
H10	−0.5261	0.3035	−0.4963	0.064*
C11	−0.6281 (4)	0.0517 (4)	−0.40156 (15)	0.0472 (8)
H11	−0.5693	−0.0335	−0.4138	0.057*
C12	−0.7875 (4)	0.0577 (5)	−0.40085 (15)	0.0525 (9)
H12	−0.8576	−0.0204	−0.4122	0.063*
C13	−0.6895 (3)	0.2756 (4)	−0.36887 (13)	0.0414 (8)
H13	−0.6831	0.3762	−0.3538	0.050*
H3O	−0.407 (5)	0.288 (5)	−0.2750 (19)	0.080*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co	0.0284 (2)	0.0353 (2)	0.0254 (2)	0.00135 (17)	−0.00314 (14)	−0.00104 (16)
O1	0.0417 (12)	0.0396 (11)	0.0279 (10)	0.0082 (9)	−0.0007 (9)	−0.0021 (9)
O2	0.093 (2)	0.083 (2)	0.0492 (15)	0.0511 (17)	0.0059 (14)	−0.0030 (14)
O3	0.0597 (14)	0.0461 (13)	0.0337 (11)	−0.0125 (12)	−0.0030 (10)	0.0008 (10)
O4	0.0294 (10)	0.0490 (13)	0.0381 (12)	0.0014 (9)	−0.0042 (9)	−0.0039 (10)
O5	0.0552 (15)	0.0479 (14)	0.0673 (16)	−0.0080 (12)	−0.0240 (12)	0.0017 (12)
N1	0.0344 (13)	0.0393 (14)	0.0419 (15)	0.0033 (11)	−0.0066 (11)	−0.0005 (12)
N2	0.0445 (16)	0.0390 (15)	0.068 (2)	0.0057 (13)	−0.0051 (14)	0.0083 (14)
N3	0.0407 (14)	0.0412 (14)	0.0280 (12)	0.0088 (11)	−0.0034 (10)	0.0003 (11)
N4	0.093 (3)	0.069 (2)	0.0389 (17)	−0.0145 (19)	−0.0282 (16)	0.0185 (15)
N5	0.0295 (13)	0.0409 (14)	0.0346 (13)	0.0011 (11)	−0.0008 (10)	−0.0006 (11)
N6	0.0281 (13)	0.0636 (18)	0.0471 (15)	0.0031 (13)	0.0009 (11)	0.0055 (14)
C1	0.0348 (16)	0.0378 (16)	0.0358 (16)	0.0038 (13)	0.0039 (12)	−0.0008 (13)
C2	0.0489 (19)	0.071 (2)	0.0310 (16)	0.0059 (18)	−0.0002 (14)	−0.0050 (16)
C3	0.0483 (19)	0.058 (2)	0.0283 (15)	0.0076 (16)	−0.0045 (13)	0.0049 (14)
C4	0.0329 (15)	0.0413 (17)	0.0361 (16)	0.0075 (14)	−0.0109 (12)	0.0065 (14)
C5	0.0462 (19)	0.050 (2)	0.0440 (19)	0.0037 (16)	−0.0064 (15)	−0.0079 (15)
C6	0.050 (2)	0.043 (2)	0.070 (2)	0.0044 (16)	−0.0021 (18)	−0.0124 (17)
C7	0.0442 (18)	0.0390 (18)	0.0483 (19)	0.0016 (14)	−0.0067 (15)	0.0037 (14)
C8	0.043 (2)	0.134 (4)	0.045 (2)	0.026 (2)	0.0060 (16)	0.030 (2)
C9	0.083 (3)	0.096 (3)	0.037 (2)	0.031 (3)	0.0153 (19)	0.020 (2)
C10	0.057 (2)	0.058 (2)	0.0449 (19)	−0.0126 (18)	−0.0190 (16)	0.0177 (17)
C11	0.0378 (17)	0.053 (2)	0.051 (2)	−0.0025 (15)	0.0042 (15)	−0.0162 (16)
C12	0.0379 (18)	0.066 (2)	0.053 (2)	−0.0123 (17)	−0.0012 (15)	−0.0133 (18)
C13	0.0361 (17)	0.0460 (19)	0.0420 (17)	0.0028 (14)	−0.0004 (13)	0.0042 (14)

Geometric parameters (Å, º)

Co—N3	2.101 (2)	N5—C11	1.363 (4)
Co—O4	2.110 (2)	N6—C13	1.327 (4)
Co—N1	2.114 (3)	N6—C12	1.357 (5)
Co—O3	2.120 (2)	N6—H6'	0.8600
Co—N5	2.127 (2)	C1—C2	1.500 (4)
Co—O1	2.141 (2)	C2—C3	1.485 (5)
O1—C1	1.252 (3)	C2—H2A	0.9700
O2—C1	1.252 (4)	C2—H2B	0.9700
O3—C3	1.451 (4)	C3—C4	1.543 (4)
O3—H3O	0.88 (4)	C3—H3	0.9800
O4—C4	1.265 (4)	C5—C6	1.358 (5)
O5—C4	1.225 (4)	C5—H5	0.9300
N1—C7	1.317 (4)	C6—H6	0.9300
N1—C5	1.368 (4)	C7—H7	0.9300
N2—C7	1.340 (4)	C8—C9	1.346 (5)
N2—C6	1.354 (5)	C8—H8	0.9300
N2—H2'	0.8600	C9—H9	0.9300
N3—C10	1.302 (4)	C10—H10	0.9300
N3—C8	1.365 (4)	C11—C12	1.354 (5)
N4—C10	1.327 (5)	C11—H11	0.9300
N4—C9	1.332 (5)	C12—H12	0.9300
N4—H4'	0.8600	C13—H13	0.9300
N5—C13	1.321 (4)
N3—Co—O4	93.18 (9)	C3—C2—H2A	108.4
N3—Co—N1	94.26 (10)	C1—C2—H2A	108.4
O4—Co—N1	91.33 (9)	C3—C2—H2B	108.4
N3—Co—O3	166.98 (9)	C1—C2—H2B	108.4
O4—Co—O3	74.92 (9)	H2A—C2—H2B	107.4
N1—Co—O3	91.33 (9)	O3—C3—C2	108.2 (3)
N3—Co—N5	93.85 (9)	O3—C3—C4	108.9 (2)
O4—Co—N5	170.50 (9)	C2—C3—C4	112.9 (3)
N1—Co—N5	94.50 (10)	O3—C3—H3	108.9
O3—Co—N5	97.43 (9)	C2—C3—H3	108.9
N3—Co—O1	89.73 (8)	C4—C3—H3	108.9
O4—Co—O1	85.21 (8)	O5—C4—O4	125.6 (3)
N1—Co—O1	174.87 (8)	O5—C4—C3	119.0 (3)
O3—Co—O1	84.11 (8)	O4—C4—C3	115.4 (3)
N5—Co—O1	88.45 (9)	C6—C5—N1	109.5 (3)
C1—O1—Co	128.69 (19)	C6—C5—H5	125.3
C3—O3—Co	106.93 (17)	N1—C5—H5	125.3
C3—O3—H3O	99 (3)	N2—C6—C5	106.0 (3)
Co—O3—H3O	94 (3)	N2—C6—H6	127.0
C4—O4—Co	112.92 (18)	C5—C6—H6	127.0
C7—N1—C5	105.8 (3)	N1—C7—N2	110.8 (3)
C7—N1—Co	125.6 (2)	N1—C7—H7	124.6
C5—N1—Co	128.6 (2)	N2—C7—H7	124.6
C7—N2—C6	108.0 (3)	C9—C8—N3	109.9 (3)
C7—N2—H2'	126.0	C9—C8—H8	125.1
C6—N2—H2'	126.0	N3—C8—H8	125.1
C10—N3—C8	104.4 (3)	N4—C9—C8	106.0 (3)
C10—N3—Co	127.3 (2)	N4—C9—H9	127.0
C8—N3—Co	128.1 (2)	C8—C9—H9	127.0
C10—N4—C9	107.7 (3)	N3—C10—N4	111.9 (3)
C10—N4—H4'	126.1	N3—C10—H10	124.0
C9—N4—H4'	126.1	N4—C10—H10	124.0
C13—N5—C11	104.9 (3)	C12—C11—N5	110.1 (3)
C13—N5—Co	125.2 (2)	C12—C11—H11	124.9
C11—N5—Co	129.8 (2)	N5—C11—H11	124.9
C13—N6—C12	107.8 (3)	C11—C12—N6	105.7 (3)
C13—N6—H6'	126.1	C11—C12—H12	127.2
C12—N6—H6'	126.1	N6—C12—H12	127.2
O2—C1—O1	120.4 (3)	N5—C13—N6	111.5 (3)
O2—C1—C2	118.3 (3)	N5—C13—H13	124.2
O1—C1—C2	121.3 (3)	N6—C13—H13	124.2
C3—C2—C1	115.6 (3)
N3—Co—O1—C1	−173.9 (2)	N3—Co—N5—C11	76.9 (3)
O4—Co—O1—C1	−80.7 (2)	O4—Co—N5—C11	−145.4 (5)
N1—Co—O1—C1	−33.0 (11)	N1—Co—N5—C11	−17.6 (3)
O3—Co—O1—C1	−5.4 (2)	O3—Co—N5—C11	−109.6 (3)
N5—Co—O1—C1	92.3 (2)	O1—Co—N5—C11	166.6 (3)
N3—Co—O3—C3	14.5 (5)	Co—O1—C1—O2	−149.6 (3)
O4—Co—O3—C3	38.95 (18)	Co—O1—C1—C2	30.2 (4)
N1—Co—O3—C3	129.97 (19)	O2—C1—C2—C3	178.7 (3)
N5—Co—O3—C3	−135.31 (19)	O1—C1—C2—C3	−1.1 (5)
O1—Co—O3—C3	−47.65 (19)	Co—O3—C3—C2	85.8 (2)
N3—Co—O4—C4	137.8 (2)	Co—O3—C3—C4	−37.3 (3)
N1—Co—O4—C4	−127.9 (2)	C1—C2—C3—O3	−61.1 (4)
O3—Co—O4—C4	−36.8 (2)	C1—C2—C3—C4	59.6 (4)
N5—Co—O4—C4	0.1 (6)	Co—O4—C4—O5	−153.9 (2)
O1—Co—O4—C4	48.3 (2)	Co—O4—C4—C3	25.7 (3)
N3—Co—N1—C7	157.4 (3)	O3—C3—C4—O5	−171.7 (3)
O4—Co—N1—C7	64.1 (3)	C2—C3—C4—O5	68.0 (4)
O3—Co—N1—C7	−10.8 (3)	O3—C3—C4—O4	8.6 (3)
N5—Co—N1—C7	−108.4 (3)	C2—C3—C4—O4	−111.6 (3)
O1—Co—N1—C7	16.6 (11)	C7—N1—C5—C6	1.0 (4)
N3—Co—N1—C5	−26.2 (3)	Co—N1—C5—C6	−175.9 (2)
O4—Co—N1—C5	−119.5 (3)	C7—N2—C6—C5	0.9 (4)
O3—Co—N1—C5	165.5 (3)	N1—C5—C6—N2	−1.2 (4)
N5—Co—N1—C5	68.0 (3)	C5—N1—C7—N2	−0.4 (4)
O1—Co—N1—C5	−167.0 (9)	Co—N1—C7—N2	176.7 (2)
O4—Co—N3—C10	−158.2 (3)	C6—N2—C7—N1	−0.3 (4)
N1—Co—N3—C10	110.2 (3)	C10—N3—C8—C9	−0.8 (5)
O3—Co—N3—C10	−134.6 (4)	Co—N3—C8—C9	−175.4 (3)
N5—Co—N3—C10	15.4 (3)	C10—N4—C9—C8	−0.1 (5)
O1—Co—N3—C10	−73.0 (3)	N3—C8—C9—N4	0.6 (6)
O4—Co—N3—C8	15.2 (3)	C8—N3—C10—N4	0.8 (4)
N1—Co—N3—C8	−76.3 (3)	Co—N3—C10—N4	175.4 (2)
O3—Co—N3—C8	38.8 (6)	C9—N4—C10—N3	−0.4 (5)
N5—Co—N3—C8	−171.2 (3)	C13—N5—C11—C12	0.3 (4)
O1—Co—N3—C8	100.4 (3)	Co—N5—C11—C12	−177.5 (2)
N3—Co—N5—C13	−100.5 (2)	N5—C11—C12—N6	0.1 (4)
O4—Co—N5—C13	37.1 (7)	C13—N6—C12—C11	−0.5 (4)
N1—Co—N5—C13	164.9 (2)	C11—N5—C13—N6	−0.7 (3)
O3—Co—N5—C13	72.9 (2)	Co—N5—C13—N6	177.34 (19)
O1—Co—N5—C13	−10.9 (2)	C12—N6—C13—N5	0.7 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O5	0.97	2.82	3.047 (4)	94
C5—H5···N3	0.93	3.00	3.356 (4)	105
C7—H7···O3	0.93	2.66	3.124 (4)	112
C8—H8···O4	0.93	2.86	3.253 (4)	107
C10—H10···N5	0.93	2.78	3.245 (4)	112
C11—H11···N1	0.93	2.98	3.369 (4)	107
C13—H13···O1	0.93	2.55	3.037 (4)	113
C13—H13···O2	0.93	2.92	3.805 (5)	159
N2—H2′···O5^i	0.86	1.99	2.828 (4)	165
N4—H4′···O1^ii	0.86	2.13	2.907 (4)	150
N4—H4′···O2^ii	0.86	2.25	3.025 (4)	149
N6—H6′···O4^iii	0.86	1.91	2.755 (3)	168
C2—H2B···O2^iv	0.97	2.98	3.591 (5)	122
O3—H3O···O2^iv	0.88 (4)	2.27 (4)	2.572 (3)	100 (3)
C2—H2B···N5^v	0.97	2.97	3.519 (4)	117
C7—H7···O5^vi	0.93	2.54	3.409 (4)	155
C11—H11···N4^vii	0.93	2.90	3.631 (5)	136

Symmetry codes: (i) x, y−1, z; (ii) −x−1, −y+1, −z−1; (iii) x−1, y, z; (iv) −x−1, y−1/2, −z−1/2; (v) −x−1, y+1/2, −z−1/2; (vi) −x, y−1/2, −z−1/2; (vii) −x−1, −y, −z−1.