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In the title compound, the coordination geometry of the CoIII atom is only slightly distorted from regular octahedral, and the racemic nature of the material was confirmed by X-ray structure analysis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100000561/qa0203sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100000561/qa0203Isup2.hkl
Contains datablock I

CCDC reference: 142934

Comment top

Studies of electron-transfer reactions between two metal centres, where 2,2'-bipyrimidine (bpm) or its ring-substituted analogues would serve as a chelating bridging ligand, included a preparation of [Co(en)2(bpm)](CF3SO3)3 complex (en = ethylenediamine) (Dixon et al., 1981) and its chloride analogue. Hovewer, under unpredictable circumstances we ended up with the title compound. Most likely, the relatively high impurity of the bpm batch (Lancaster Syntheses Ltd) used for the preparation without purification is responsible for such a result. In order to understand unusual `reaction path', the products obtained were characterized by X-ray structure analysis. The analysis revealed bis(ethylenediamine)(pyrimidin-2-ylcarboxylato)cobalt(III) bis(trifluoromethanesulfonate) dihydrate, (I), and its chloride analogue. As 2,2'-bipyrimidine was not coordinated to the metal atom, the analysis of the commercial chemical was undertaken. It revealed the presence of pyrimidine-2-carboxylic acid which has been of higher preference to be coordinated via mixed O,N-donated ligands than N,N of bpm. Due to the low quality of the data collected for bis(ethylenediamine)(pyrimidine-2-carboxylato)cobalt(III) chloride 1.5-hydrate, (II), the detailed description of crystal and molecular structure will be given only for bis(ethylenediamine)(pyrimidin-2-ylcarboxylato)cobalt(III) bis(trifluoromethanesulfonate) dihydrate, (I).

The solved structures revealed the same cation structure with ethylenediamine as a bidentate ligands. Cobalt is in a 3+ oxidation state and two ethylenediamine ligands and pyrimidinyl-2-carboxylato ligand (which was supposed to be bpm) built an octahedral environment. Tris-bidentate ligands in the complexes might introduce certain degree of octahedral distortion. However, the title complex reveals minor octahedral distortion. In the structures with different ligands electron-donating ability of nitrogen varies, thus Co—N bond lengths might be different. Here, five Co—N bonds with mean value 1.952 (2) Å are all nearly equal. The bite angle values range from 83.84 (7) to 86.60 (8)°. Other bonding angles do not deviate significantly from 90° (<2°). In the synthesis of (II), optically pure, Δ absolute configuration was obtained whereas in (I), the racemate appeared. Chirality of these complexes can be deduced from the space-group symmetry. Three-dimensional hydrogen-bond network involves: (a) N—H···O between ethylenediamine ligands and trifluoromethanesulfonates in the [111] direction; (b) N—H···N between ethylenediamine ligands and N atoms of pyrimidine-2-carboxylato ligand; (c) O—H···O between crystalline water molecules and crystalline water molecules towards trifluoromethanesulfonate anions.

Experimental top

Crystals of both compounds were grown by slow evaporation from ethanol and acetone mixtures affording acceptable crystallographic samples. The crystals obtained were used for intensity data collection. In order to minimize crystal decay, the data for (I) were collected at low temperature (100 K), while the data for (II) were collected at room temperature.

Refinement top

H atoms were located from a different synthesis and refined isotropically.

Computing details top

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: HELENA (Spek, 1997b); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997b); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997b).

bis(ethylenediamine)pyrimidinyl-2-carboxylato Co(3+) trifluoromethanesulfonate dihydrate top
Crystal data top
[Co(C5H3N2O2)(C2H8N2)2](CF3O3S)2·2H2OZ = 2
Mr = 636.42F(000) = 648
Triclinic, P1Dx = 1.881 Mg m3
a = 6.4976 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.729 (1) ÅCell parameters from 25 reflections
c = 14.741 (1) Åθ = 20–24°
α = 73.40 (1)°µ = 1.06 mm1
β = 81.98 (1)°T = 100 K
γ = 74.61 (1)°Prismatic, orange
V = 1123.8 (2) Å30.28 × 0.28 × 0.10 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
4867 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.030
Graphite monochromatorθmax = 30.4°, θmin = 2.5°
ω/2θ scansh = 09
Absorption correction: ψ scan
(PLATON97; Spek, 1997a)
k = 1718
Tmin = 0.817, Tmax = 0.899l = 2020
7328 measured reflections3 standard reflections every 87 reflections
6780 independent reflections intensity decay: 0.7%
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)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099All H-atom parameters refined
S = 0.95Calculated w = 1/[σ2(Fo2) + (0.045P)2 + 1.1493P]
where P = (Fo2 + 2Fc2)/3
6780 reflections(Δ/σ)max = 0.014
417 parametersΔρmax = 0.63 e Å3
0 restraintsΔρmin = 0.48 e Å3
Crystal data top
[Co(C5H3N2O2)(C2H8N2)2](CF3O3S)2·2H2Oγ = 74.61 (1)°
Mr = 636.42V = 1123.8 (2) Å3
Triclinic, P1Z = 2
a = 6.4976 (4) ÅMo Kα radiation
b = 12.729 (1) ŵ = 1.06 mm1
c = 14.741 (1) ÅT = 100 K
α = 73.40 (1)°0.28 × 0.28 × 0.10 mm
β = 81.98 (1)°
Data collection top
Enraf-Nonius CAD-4
diffractometer
4867 reflections with I > 2σ(I)
Absorption correction: ψ scan
(PLATON97; Spek, 1997a)
Rint = 0.030
Tmin = 0.817, Tmax = 0.8993 standard reflections every 87 reflections
7328 measured reflections intensity decay: 0.7%
6780 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0370 restraints
wR(F2) = 0.099All H-atom parameters refined
S = 0.95Δρmax = 0.63 e Å3
6780 reflectionsΔρmin = 0.48 e Å3
417 parameters
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
Co10.27444 (5)0.03937 (3)0.77233 (2)0.00817 (8)
N10.1381 (3)0.15845 (18)0.66682 (14)0.0127 (4)
H11N0.022 (5)0.194 (3)0.689 (2)0.017 (8)*
H12N0.115 (5)0.129 (3)0.625 (2)0.014 (7)*
C10.2849 (4)0.2345 (2)0.62385 (17)0.0134 (4)
H110.247 (4)0.277 (2)0.563 (2)0.009 (7)*
H120.278 (4)0.282 (2)0.6652 (19)0.009 (7)*
C20.5065 (4)0.1593 (2)0.61894 (16)0.0137 (4)
H210.618 (4)0.206 (2)0.5974 (19)0.008 (6)*
H220.512 (5)0.114 (2)0.574 (2)0.015 (7)*
N20.5417 (3)0.08153 (17)0.71597 (14)0.0110 (4)
H21N0.589 (4)0.117 (2)0.7491 (19)0.007 (6)*
H22N0.650 (5)0.018 (3)0.711 (2)0.023 (8)*
N30.4234 (3)0.07992 (17)0.87463 (14)0.0107 (4)
H31N0.328 (5)0.099 (3)0.921 (2)0.022 (8)*
H32N0.507 (5)0.052 (2)0.894 (2)0.014 (7)*
C30.5282 (4)0.1810 (2)0.83923 (18)0.0145 (4)
H310.663 (4)0.168 (2)0.8079 (18)0.004 (6)*
H320.552 (5)0.247 (3)0.890 (2)0.021 (8)*
C40.3802 (4)0.1881 (2)0.77187 (18)0.0148 (4)
H410.452 (5)0.244 (2)0.739 (2)0.013 (7)*
H420.247 (5)0.205 (2)0.805 (2)0.017 (7)*
N40.3223 (3)0.07507 (17)0.70356 (14)0.0119 (4)
H41N0.425 (5)0.068 (3)0.657 (2)0.024 (8)*
H42N0.193 (6)0.066 (3)0.684 (3)0.036 (10)*
N50.1903 (3)0.13991 (16)0.85708 (13)0.0091 (3)
C50.2895 (4)0.2116 (2)0.87482 (16)0.0119 (4)
H50.417 (5)0.223 (2)0.841 (2)0.018 (8)*
C60.2029 (4)0.2689 (2)0.94357 (17)0.0133 (4)
H60.276 (5)0.321 (2)0.954 (2)0.013 (7)*
C70.0151 (4)0.2490 (2)0.99339 (17)0.0140 (4)
H70.055 (5)0.288 (2)1.041 (2)0.012 (7)*
N60.0873 (3)0.17898 (16)0.97499 (13)0.0113 (4)
C80.0042 (3)0.12876 (18)0.90764 (15)0.0092 (4)
C90.1016 (3)0.04899 (18)0.88281 (15)0.0092 (4)
O70.0062 (2)0.00158 (14)0.81920 (11)0.0110 (3)
O80.2755 (3)0.03443 (14)0.92236 (11)0.0123 (3)
S10.10777 (9)0.14576 (5)0.41580 (4)0.01303 (12)
O10.0886 (3)0.09320 (15)0.34281 (12)0.0165 (4)
O20.3267 (3)0.13434 (16)0.43357 (12)0.0175 (4)
O30.0354 (3)0.12652 (17)0.49948 (13)0.0221 (4)
C100.0103 (4)0.2962 (2)0.35977 (18)0.0169 (5)
F10.0049 (3)0.35803 (13)0.41964 (11)0.0229 (3)
F20.1345 (3)0.33033 (13)0.28278 (11)0.0245 (3)
F30.1878 (3)0.31634 (15)0.33318 (13)0.0298 (4)
S20.28482 (9)0.61881 (5)0.24925 (4)0.01280 (12)
O40.0746 (3)0.60365 (16)0.24621 (15)0.0248 (4)
O50.4458 (3)0.57489 (17)0.18328 (14)0.0267 (4)
O60.2864 (3)0.73205 (14)0.25284 (12)0.0151 (3)
C110.3704 (4)0.5329 (2)0.36573 (19)0.0209 (5)
F40.3916 (3)0.42384 (13)0.37522 (13)0.0277 (4)
F50.5591 (3)0.54570 (16)0.37952 (15)0.0398 (5)
F60.2283 (4)0.56298 (18)0.43291 (13)0.0500 (6)
O90.2497 (4)0.45926 (18)0.07490 (15)0.0279 (5)
H910.304 (7)0.498 (4)0.105 (3)0.060 (13)*
H920.119 (7)0.457 (3)0.094 (3)0.049 (13)*
O100.8285 (4)0.43453 (18)0.11212 (16)0.0265 (4)
H1010.740 (7)0.461 (4)0.153 (3)0.056 (13)*
H1020.779 (8)0.461 (4)0.061 (4)0.062 (15)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Co10.0054 (1)0.0120 (2)0.0081 (1)0.0016 (1)0.0011 (1)0.0053 (1)
N10.0081 (9)0.0184 (10)0.0118 (9)0.0023 (8)0.0025 (7)0.0066 (8)
C10.0121 (11)0.0160 (11)0.0111 (10)0.0033 (9)0.0007 (8)0.0025 (9)
C20.0121 (10)0.0186 (11)0.0098 (10)0.0039 (9)0.0017 (8)0.0036 (9)
N20.0093 (9)0.0134 (9)0.0120 (9)0.0036 (7)0.0007 (7)0.0058 (7)
N30.0085 (9)0.0143 (9)0.0110 (9)0.0031 (7)0.0002 (7)0.0058 (7)
C30.0138 (11)0.0119 (11)0.0172 (11)0.0005 (9)0.0006 (9)0.0063 (9)
C40.0153 (11)0.0128 (11)0.0177 (11)0.0037 (9)0.0015 (9)0.0070 (9)
N40.0076 (9)0.0167 (10)0.0137 (9)0.0036 (7)0.0013 (7)0.0078 (8)
N50.0061 (8)0.0117 (9)0.0097 (8)0.0015 (7)0.0001 (6)0.0042 (7)
C50.0102 (10)0.0137 (10)0.0125 (10)0.0041 (8)0.0006 (8)0.0035 (8)
C60.0149 (11)0.0117 (10)0.0142 (10)0.0028 (9)0.0003 (8)0.0053 (8)
C70.0161 (11)0.0131 (11)0.0132 (10)0.0011 (9)0.0001 (9)0.0069 (8)
N60.0106 (9)0.0124 (9)0.0104 (9)0.0009 (7)0.0019 (7)0.0052 (7)
C80.0067 (9)0.0096 (9)0.0102 (9)0.0004 (7)0.0006 (7)0.0031 (8)
C90.0080 (9)0.0093 (9)0.0094 (9)0.0004 (8)0.0016 (7)0.0021 (8)
O70.0075 (7)0.0156 (8)0.0120 (7)0.0035 (6)0.0012 (6)0.0072 (6)
O80.0070 (7)0.0161 (8)0.0137 (8)0.0025 (6)0.0024 (6)0.0056 (6)
S10.0098 (2)0.0187 (3)0.0128 (3)0.0030 (2)0.0023 (2)0.0093 (2)
O10.0140 (8)0.0219 (9)0.0173 (8)0.0023 (7)0.0000 (7)0.0132 (7)
O20.0102 (8)0.0262 (10)0.0174 (8)0.0008 (7)0.0028 (6)0.0103 (7)
O30.0214 (10)0.0296 (10)0.0187 (9)0.0110 (8)0.0110 (7)0.0129 (8)
C100.0126 (11)0.0210 (12)0.0194 (12)0.0003 (9)0.0018 (9)0.0119 (10)
F10.0240 (8)0.0240 (8)0.0255 (8)0.0039 (7)0.0009 (6)0.0166 (7)
F20.0300 (9)0.0220 (8)0.0178 (7)0.0032 (7)0.0034 (6)0.0044 (6)
F30.0163 (8)0.0333 (9)0.0431 (10)0.0046 (7)0.0124 (7)0.0196 (8)
S20.0121 (3)0.0131 (3)0.0129 (3)0.0014 (2)0.0004 (2)0.0049 (2)
O40.0169 (9)0.0224 (10)0.0366 (11)0.0053 (8)0.0092 (8)0.0060 (8)
O50.0282 (11)0.0274 (10)0.0221 (10)0.0007 (8)0.0090 (8)0.0130 (8)
O60.0144 (8)0.0136 (8)0.0165 (8)0.0019 (6)0.0019 (6)0.0052 (6)
C110.0206 (13)0.0195 (12)0.0202 (12)0.0019 (10)0.0026 (10)0.0032 (10)
F40.0228 (8)0.0154 (8)0.0391 (10)0.0035 (6)0.0059 (7)0.0029 (7)
F50.0391 (11)0.0298 (10)0.0528 (12)0.0135 (8)0.0319 (10)0.0044 (9)
F60.0664 (15)0.0469 (12)0.0158 (8)0.0123 (11)0.0095 (9)0.0049 (8)
O90.0352 (13)0.0251 (11)0.0250 (11)0.0044 (9)0.0046 (9)0.0103 (8)
O100.0327 (12)0.0240 (10)0.0199 (10)0.0020 (9)0.0010 (9)0.0104 (8)
Geometric parameters (Å, º) top
Co1—O71.915 (2)C8—C91.514 (3)
Co1—N41.940 (2)C9—O81.232 (3)
Co1—N11.956 (2)C9—O71.284 (3)
Co1—N21.957 (2)S1—O31.441 (2)
Co1—N31.959 (2)S1—O21.444 (2)
Co1—N51.962 (2)S1—O11.454 (2)
N1—C11.490 (3)S1—C101.830 (3)
C1—C21.508 (3)C10—F11.332 (3)
C2—N21.497 (3)C10—F21.333 (3)
N3—C31.487 (3)C10—F31.336 (3)
C3—C41.511 (3)S2—O51.439 (2)
C4—N41.489 (3)S2—O41.438 (2)
N5—C81.348 (3)S2—O61.460 (2)
N5—C51.346 (3)S2—C111.823 (3)
C5—C61.386 (3)C11—F61.324 (3)
C6—C71.379 (3)C11—F51.329 (3)
C7—N61.346 (3)C11—F41.326 (3)
N6—C81.321 (3)
O7—Co1—N486.59 (8)N6—C8—C9119.36 (19)
O7—Co1—N190.64 (8)N5—C8—C9114.41 (18)
N4—Co1—N192.61 (9)O8—C9—O7125.8 (2)
O7—Co1—N2176.19 (8)O8—C9—C8120.35 (19)
N4—Co1—N291.78 (9)O7—C9—C8113.84 (19)
N1—Co1—N285.99 (8)C9—O7—Co1116.12 (14)
O7—Co1—N391.79 (8)O3—S1—O2115.01 (11)
N4—Co1—N386.60 (8)O3—S1—O1115.96 (11)
N1—Co1—N3177.40 (9)O2—S1—O1113.37 (10)
N2—Co1—N391.55 (9)O3—S1—C10103.14 (12)
O7—Co1—N583.84 (7)O2—S1—C10104.42 (11)
N4—Co1—N5169.61 (8)O1—S1—C10102.72 (11)
N1—Co1—N591.54 (8)F1—C10—F2108.5 (2)
N2—Co1—N598.01 (8)F1—C10—F3108.04 (19)
N3—Co1—N589.65 (8)F2—C10—F3107.9 (2)
C1—N1—Co1108.62 (15)F1—C10—S1111.00 (17)
N1—C1—C2106.43 (19)F2—C10—S1111.12 (16)
N2—C2—C1106.77 (18)F3—C10—S1110.11 (18)
C2—N2—Co1109.38 (14)O5—S2—O4115.46 (13)
C3—N3—Co1109.36 (14)O5—S2—O6113.88 (11)
N3—C3—C4106.73 (19)O4—S2—O6113.86 (11)
N4—C4—C3107.56 (19)O5—S2—C11104.53 (12)
C4—N4—Co1108.50 (15)O4—S2—C11104.78 (13)
C8—N5—C5117.03 (19)O6—S2—C11102.44 (11)
C8—N5—Co1111.64 (15)F6—C11—F5109.0 (3)
C5—N5—Co1131.26 (16)F6—C11—F4108.0 (2)
N5—C5—C6120.4 (2)F5—C11—F4107.2 (2)
C7—C6—C5118.0 (2)F6—C11—S2110.02 (18)
N6—C7—C6122.0 (2)F5—C11—S2110.44 (19)
C8—N6—C7116.3 (2)F4—C11—S2112.11 (19)
N6—C8—N5126.2 (2)
N1—Co1—O7—C994.09O3—S1—C10—F364.09
N3—Co1—O7—C986.85O3—S1—C10—F2176.38
N4—Co1—O7—C9173.33O4—S2—C11—F655.70
N5—Co1—O7—C92.61O5—S2—C11—F6177.55
O7—Co1—N1—C1164.22O6—S2—C11—F663.42
N2—Co1—N1—C117.56O5—S2—C11—F457.32
N4—Co1—N1—C1109.16O6—S2—C11—F4176.36
N5—Co1—N1—C180.36O4—S2—C11—F464.52
N1—Co1—N2—C211.24O5—S2—C11—F562.14
N3—Co1—N2—C2167.91O6—S2—C11—F556.90
N4—Co1—N2—C281.26O4—S2—C11—F5176.01
N5—Co1—N2—C2102.23Co1—O7—C9—O8178.99
O7—Co1—N3—C398.13Co1—O7—C9—C81.10
N2—Co1—N3—C380.04Co1—N1—C1—C242.20
N4—Co1—N3—C311.65Co1—N2—C2—C137.17
N5—Co1—N3—C3178.04Co1—N3—C3—C436.32
O7—Co1—N4—C475.75Co1—N4—C4—C340.43
N1—Co1—N4—C4166.23Co1—N5—C5—C6175.62
N2—Co1—N4—C4107.70Co1—N5—C8—N6175.24
N3—Co1—N4—C416.25C5—N5—C8—N62.09
O7—Co1—N5—C5179.56Co1—N5—C8—C93.94
N1—Co1—N5—C589.09C5—N5—C8—C9178.73
N2—Co1—N5—C52.91C8—N5—C5—C61.08
N3—Co1—N5—C588.60C7—N6—C8—C9179.90
O7—Co1—N5—C83.60C8—N6—C7—C61.19
N1—Co1—N5—C894.07C7—N6—C8—N50.95
N2—Co1—N5—C8179.75N1—C1—C2—N251.48
N3—Co1—N5—C888.23N3—C3—C4—N450.02
O1—S1—C10—F262.72N5—C5—C6—C70.83
O1—S1—C10—F356.81C5—C6—C7—N62.04
O2—S1—C10—F3175.36N6—C8—C9—O82.85
O1—S1—C10—F1176.40N5—C8—C9—O8177.91
O2—S1—C10—F165.05N6—C8—C9—O7177.24
O3—S1—C10—F155.50N5—C8—C9—O72.01
O2—S1—C10—F255.82
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H11N···O6i0.852.152.991 (3)174 (3)
N1—H12N···O30.862.223.019 (2)155 (3)
N2—H21N···O6ii0.882.273.044 (3)147 (2)
N2—H22N···O1iii0.942.123.025 (3)162 (3)
N3—H31N···N6iv0.882.263.129 (3)167 (3)
N3—H32N···O8v0.842.152.987 (3)172 (3)
N4—H41N···O2iii0.892.102.921 (3)152 (3)
N4—H42N···O1vi0.892.062.928 (3)164 (4)
O9—H91···O50.912.133.042 (3)175 (4)
O9—H92···O10vii0.861.962.798 (4)166 (4)
O10—H101···O50.852.152.908 (3)149 (4)
O10—H102···O9viii0.811.982.754 (2)161 (5)
Symmetry codes: (i) x, y+1, z+1; (ii) x+1, y+1, z+1; (iii) x+1, y, z+1; (iv) x, y, z+2; (v) x+1, y, z; (vi) x, y, z+1; (vii) x1, y, z; (viii) x+1, y+1, z.

Experimental details

Crystal data
Chemical formula[Co(C5H3N2O2)(C2H8N2)2](CF3O3S)2·2H2O
Mr636.42
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)6.4976 (4), 12.729 (1), 14.741 (1)
α, β, γ (°)73.40 (1), 81.98 (1), 74.61 (1)
V3)1123.8 (2)
Z2
Radiation typeMo Kα
µ (mm1)1.06
Crystal size (mm)0.28 × 0.28 × 0.10
Data collection
DiffractometerEnraf-Nonius CAD-4
diffractometer
Absorption correctionψ scan
(PLATON97; Spek, 1997a)
Tmin, Tmax0.817, 0.899
No. of measured, independent and
observed [I > 2σ(I)] reflections
7328, 6780, 4867
Rint0.030
(sin θ/λ)max1)0.712
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.099, 0.95
No. of reflections6780
No. of parameters417
H-atom treatmentAll H-atom parameters refined
Δρmax, Δρmin (e Å3)0.63, 0.48

Computer programs: CAD-4 Software (Enraf-Nonius, 1989), CAD-4 Software, HELENA (Spek, 1997b), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997b).

Selected geometric parameters (Å, º) top
Co1—O71.915 (2)C8—C91.514 (3)
Co1—N41.940 (2)C9—O81.232 (3)
Co1—N11.956 (2)C9—O71.284 (3)
Co1—N21.957 (2)S1—O31.441 (2)
Co1—N31.959 (2)S1—O21.444 (2)
Co1—N51.962 (2)S1—O11.454 (2)
N1—C11.490 (3)S1—C101.830 (3)
C1—C21.508 (3)C10—F11.332 (3)
C2—N21.497 (3)C10—F21.333 (3)
N3—C31.487 (3)C10—F31.336 (3)
C3—C41.511 (3)S2—O51.439 (2)
C4—N41.489 (3)S2—O41.438 (2)
N5—C81.348 (3)S2—O61.460 (2)
N5—C51.346 (3)S2—C111.823 (3)
C5—C61.386 (3)C11—F61.324 (3)
C6—C71.379 (3)C11—F51.329 (3)
C7—N61.346 (3)C11—F41.326 (3)
N6—C81.321 (3)
O7—Co1—N486.59 (8)N6—C8—C9119.36 (19)
O7—Co1—N190.64 (8)N5—C8—C9114.41 (18)
N4—Co1—N192.61 (9)O8—C9—O7125.8 (2)
O7—Co1—N2176.19 (8)O8—C9—C8120.35 (19)
N4—Co1—N291.78 (9)O7—C9—C8113.84 (19)
N1—Co1—N285.99 (8)C9—O7—Co1116.12 (14)
O7—Co1—N391.79 (8)O3—S1—O2115.01 (11)
N4—Co1—N386.60 (8)O3—S1—O1115.96 (11)
N1—Co1—N3177.40 (9)O2—S1—O1113.37 (10)
N2—Co1—N391.55 (9)O3—S1—C10103.14 (12)
O7—Co1—N583.84 (7)O2—S1—C10104.42 (11)
N4—Co1—N5169.61 (8)O1—S1—C10102.72 (11)
N1—Co1—N591.54 (8)F1—C10—F2108.5 (2)
N2—Co1—N598.01 (8)F1—C10—F3108.04 (19)
N3—Co1—N589.65 (8)F2—C10—F3107.9 (2)
C1—N1—Co1108.62 (15)F1—C10—S1111.00 (17)
N1—C1—C2106.43 (19)F2—C10—S1111.12 (16)
N2—C2—C1106.77 (18)F3—C10—S1110.11 (18)
C2—N2—Co1109.38 (14)O5—S2—O4115.46 (13)
C3—N3—Co1109.36 (14)O5—S2—O6113.88 (11)
N3—C3—C4106.73 (19)O4—S2—O6113.86 (11)
N4—C4—C3107.56 (19)O5—S2—C11104.53 (12)
C4—N4—Co1108.50 (15)O4—S2—C11104.78 (13)
C8—N5—C5117.03 (19)O6—S2—C11102.44 (11)
C8—N5—Co1111.64 (15)F6—C11—F5109.0 (3)
C5—N5—Co1131.26 (16)F6—C11—F4108.0 (2)
N5—C5—C6120.4 (2)F5—C11—F4107.2 (2)
C7—C6—C5118.0 (2)F6—C11—S2110.02 (18)
N6—C7—C6122.0 (2)F5—C11—S2110.44 (19)
C8—N6—C7116.3 (2)F4—C11—S2112.11 (19)
N6—C8—N5126.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H11N···O6i0.852.152.991 (3)174 (3)
N1—H12N···O30.862.223.019 (2)155 (3)
N2—H21N···O6ii0.882.273.044 (3)147 (2)
N2—H22N···O1iii0.942.123.025 (3)162 (3)
N3—H31N···N6iv0.882.263.129 (3)167 (3)
N3—H32N···O8v0.842.152.987 (3)172 (3)
N4—H41N···O2iii0.892.102.921 (3)152 (3)
N4—H42N···O1vi0.892.062.928 (3)164 (4)
O9—H91···O50.912.133.042 (3)175 (4)
O9—H92···O10vii0.861.962.798 (4)166 (4)
O10—H101···O50.852.152.908 (3)149 (4)
O10—H102···O9viii0.811.982.754 (2)161 (5)
Symmetry codes: (i) x, y+1, z+1; (ii) x+1, y+1, z+1; (iii) x+1, y, z+1; (iv) x, y, z+2; (v) x+1, y, z; (vi) x, y, z+1; (vii) x1, y, z; (viii) x+1, y+1, z.
 

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