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The structure of the title compound, [Co(C2N3)2(C4H7NO)2]n, which was reported in space group Cm [Sun et al. (2001). Inorg. Chem. Commun. 4, 72–75], was rerefined in the centrosymmetric space group C2/m to reveal a close analogy with the structure of the Co–dicyan­amide complex with N,N-di­methyl­form­amide. The Co atom and the dicyan­amide bridging ligand occupy special positions of symmetry 2/m and m, respectively.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680301362X/ya6167sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680301362X/ya6167Isup2.hkl
Contains datablock I

CCDC reference: 196403

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.030
  • wR factor = 0.082
  • Data-to-parameter ratio = 14.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
PLAT_710 Alert C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 18 CO1 -N2 -C5 -N3 -135.00 2.00 1.555 1.555 1.555 1.555
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Comment top

The structure of the title compound, (I), which was reported in the Cm space group (Sun et al., 2001), was rerefined in the centrosymmetric C2/m space group to reveal a close analogy with the structure of the Co–dicyanamide complex with N,N-dimethylformamide (Tong et al., 2003). A pair of L-shaped dicyanamido anions link the bis(2-pyrrolidone)cobalt(II) units into a linear chain running along the b axis of the crystal (Fig. 1) The Co atom and the dicyanamide bridging ligand occupy special positions of symmetry 2/m and m, respectively. Adjacent chains are linked by an N—H···N hydrogen bond [3.072 (3) Å], giving rise to layers parallel to the ab plane of the crystal (Fig. 2). The same paper by Sun et al. (2001) also mentions (but does not provide full structural details for) the isostructural Mn complex. It is likely that this complex should also be rerefined in the C2/m space group.

Experimental top

PLEASE PROVIDE SOME PREPARATION DETAILS OR A REFERENCE TO THE SYNTHESIS

Refinement top

The diffraction measurements were those used in the original refinement (Sun et al., 2001). The aliphatic H atoms were generated geometrically (C—H = 0.97 Å) and were allowed to ride on their parent C atoms in the riding-model approximation; their displacement parameters were set to 1.2 times those of the C atoms. The amide H atom was located and refined [N1—H1 = 0.83 (3) Å].

Computing details top

Data collection: KappaCCD Software (Nonius, 1998); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. ORTEPII (Johnson, 1976) plot depicting a fragment of the structure. Displacement ellipsoids are plotted at the 50% probability level; H atoms are shown as small spheres of arbitrary radii. [Symmetry codes: (i) 1 − x, 1 − y, 1 − z; (ii) x, 1 − y, z; (iii) 1 − x, y, 1 − z.]
[Figure 2] Fig. 2. ORTEPII (Johnson, 1976) plot of the hydrogen-bonded layer structure.
catena-poly[[bis(2-pyrrolidone-κO)cobalt(II)]-di-µ-1,5-dicyanamido- κ4N1:N5] top
Crystal data top
[Co(C2N3)2(C4H7NO)2]F(000) = 370
Mr = 361.24Dx = 1.684 Mg m3
Monoclinic, C2/mMo Kα radiation, λ = 0.71073 Å
a = 15.420 (3) ÅCell parameters from 6994 reflections
b = 7.220 (1) Åθ = 4.1–28.5°
c = 6.950 (1) ŵ = 1.23 mm1
β = 112.94 (3)°T = 298 K
V = 712.6 (2) Å3Block, pink
Z = 20.25 × 0.23 × 0.23 mm
Data collection top
Nonius KappaCCD
diffractometer
949 independent reflections
Radiation source: fine-focus sealed tube903 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
Detector resolution: 0.76 pixels mm-1θmax = 28.5°, θmin = 4.1°
ϕ scansh = 2020
Absorption correction: multi-scan
(Blessing, 1995)
k = 99
Tmin = 0.712, Tmax = 0.754l = 99
6996 measured reflections
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)] = 0.030Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0546P)2 + 0.4762P]
where P = (Fo2 + 2Fc2)/3
949 reflections(Δ/σ)max = 0.001
68 parametersΔρmax = 0.43 e Å3
0 restraintsΔρmin = 0.41 e Å3
Crystal data top
[Co(C2N3)2(C4H7NO)2]V = 712.6 (2) Å3
Mr = 361.24Z = 2
Monoclinic, C2/mMo Kα radiation
a = 15.420 (3) ŵ = 1.23 mm1
b = 7.220 (1) ÅT = 298 K
c = 6.950 (1) Å0.25 × 0.23 × 0.23 mm
β = 112.94 (3)°
Data collection top
Nonius KappaCCD
diffractometer
949 independent reflections
Absorption correction: multi-scan
(Blessing, 1995)
903 reflections with I > 2σ(I)
Tmin = 0.712, Tmax = 0.754Rint = 0.033
6996 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0300 restraints
wR(F2) = 0.082H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.43 e Å3
949 reflectionsΔρmin = 0.41 e Å3
68 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Co10.50000.50000.50000.0242 (2)
O10.6426 (1)0.50000.6958 (3)0.034 (1)
N10.7781 (1)0.50000.9799 (3)0.035 (1)
N20.5315 (1)0.2911 (2)0.3290 (2)0.033 (1)
N30.5844 (2)0.00000.2424 (4)0.035 (1)
C10.6859 (2)0.50000.8873 (4)0.029 (1)
C20.6462 (2)0.50001.0505 (4)0.045 (1)
C30.7281 (2)0.50001.2534 (5)0.075 (1)
C40.8145 (2)0.50001.2060 (4)0.039 (1)
C50.5545 (1)0.1516 (2)0.2916 (2)0.026 (1)
H10.812 (2)0.50000.912 (5)0.033 (7)*
H2a0.60770.60921.03780.054*0.50
H2b0.60770.39081.03780.054*0.50
H3a0.72680.39091.33380.090*0.50
H3b0.72680.60911.33380.090*0.50
H4a0.85240.60941.26270.047*0.50
H4b0.85240.39061.26270.047*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Co10.0282 (2)0.0182 (2)0.0287 (2)0.0000.0138 (2)0.000
O10.030 (1)0.043 (1)0.030 (1)0.0000.012 (1)0.000
N10.026 (1)0.045 (1)0.036 (1)0.0000.016 (1)0.000
N20.042 (1)0.025 (1)0.039 (1)0.000 (1)0.023 (1)0.002 (1)
N30.047 (1)0.023 (1)0.049 (1)0.0000.034 (1)0.000
C10.028 (1)0.027 (1)0.033 (1)0.0000.014 (1)0.000
C20.031 (1)0.077 (2)0.032 (1)0.0000.017 (1)0.000
C30.036 (2)0.156 (4)0.033 (1)0.0000.015 (1)0.000
C40.031 (1)0.046 (1)0.035 (1)0.0000.008 (1)0.000
C50.029 (1)0.025 (1)0.027 (1)0.003 (1)0.015 (1)0.002 (1)
Geometric parameters (Å, º) top
Co1—O12.087 (2)N3—C5iv1.284 (2)
Co1—O1i2.087 (2)C1—C21.484 (3)
Co1—N22.091 (1)C2—C31.482 (4)
Co1—N2ii2.091 (1)C3—C41.493 (4)
Co1—N2i2.091 (1)N1—H10.83 (3)
Co1—N2iii2.091 (1)C2—H2a0.97
O1—C11.235 (3)C2—H2b0.97
N1—C11.312 (3)C3—H3a0.97
N1—C41.448 (3)C3—H3b0.97
N2—C51.131 (2)C4—H4a0.97
N3—C51.284 (2)C4—H4b0.97
O1—Co1—O1i180.0C3—C2—C1105.9 (2)
O1—Co1—N287.2 (1)C2—C3—C4107.0 (2)
O1—Co1—N2ii87.2 (1)N1—C4—C3103.8 (2)
O1—Co1—N2i92.8 (1)N2—C5—N3175.5 (2)
O1—Co1—N2iii92.8 (1)C1—N1—H1122 (2)
O1i—Co1—N292.8 (1)C4—N1—H1123 (2)
O1i—Co1—N2ii92.8 (1)C3—C2—H2a110.5
O1i—Co1—N2i87.2 (1)C1—C2—H2a110.5
O1i—Co1—N2iii87.2 (1)C3—C2—H2b110.5
N2—Co1—N2ii92.3 (1)C1—C2—H2b110.5
N2—Co1—N2i180.0H2a—C2—H2b108.7
N2—Co1—N2iii87.7 (1)C2—C3—H3a110.3
N2ii—Co1—N2i87.7 (1)C4—C3—H3a110.3
N2ii—Co1—N2iii180.0 (1)C2—C3—H3b110.3
N2i—Co1—N2iii92.3 (1)C4—C3—H3b110.3
C1—O1—Co1133.9 (2)H3a—C3—H3b108.6
C1—N1—C4114.8 (2)N1—C4—H4a111.0
C5—N2—Co1159.4 (1)C3—C4—H4a111.0
C5iv—N3—C5116.9 (2)N1—C4—H4b111.0
O1—C1—N1123.8 (2)C3—C4—H4b111.0
O1—C1—C2127.8 (2)H4a—C4—H4b109.0
N1—C1—C2108.5 (2)
N2i—Co1—O1—C146.2 (1)Co1—O1—C1—C20.0
N2—Co1—O1—C1133.8 (1)C4—N1—C1—O1180.0
N2ii—Co1—O1—C1133.8 (1)C4—N1—C1—C20.0
N2iii—Co1—O1—C146.2 (1)O1—C1—C2—C3180.0
O1i—Co1—N2—C5115.1 (4)N1—C1—C2—C30.0
O1—Co1—N2—C564.9 (4)C1—C2—C3—C40.0
N2ii—Co1—N2—C5152.0 (3)C1—N1—C4—C30.0
N2iii—Co1—N2—C528.0 (3)C2—C3—C4—N10.0
Co1—O1—C1—N1180.0Co1—N2—C5—N3135 (2)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y+1, z; (iii) x+1, y, z+1; (iv) x, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N3v0.83 (3)2.24 (3)3.072 (3)175 (3)
Symmetry code: (v) x+3/2, y+1/2, z+1.

Experimental details

Crystal data
Chemical formula[Co(C2N3)2(C4H7NO)2]
Mr361.24
Crystal system, space groupMonoclinic, C2/m
Temperature (K)298
a, b, c (Å)15.420 (3), 7.220 (1), 6.950 (1)
β (°) 112.94 (3)
V3)712.6 (2)
Z2
Radiation typeMo Kα
µ (mm1)1.23
Crystal size (mm)0.25 × 0.23 × 0.23
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correctionMulti-scan
(Blessing, 1995)
Tmin, Tmax0.712, 0.754
No. of measured, independent and
observed [I > 2σ(I)] reflections
6996, 949, 903
Rint0.033
(sin θ/λ)max1)0.671
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.030, 0.082, 1.03
No. of reflections949
No. of parameters68
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.43, 0.41

Computer programs: KappaCCD Software (Nonius, 1998), HKL SCALEPACK (Otwinowski & Minor, 1997), DENZO SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976), SHELXL97.

 

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