[2-(N,N-Dimethylcarbamoyl)ethyl]bis(dimethylglyoximato)[(R)-1-phenylethylamine]cobalt(III)
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801001088/cf6035sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801001088/cf6035Isup2.hkl |
CCDC reference: 159705
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.010 Å
- R factor = 0.045
- wR factor = 0.122
- Data-to-parameter ratio = 9.9
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
WEIGH_01 Alert C Extra text has been found in the _refine_ls_weighting_scheme field. This should be in the _refine_ls_weighting_details field. Weighting scheme given as calc w = 1/[\s^2^(Fo^2^)+(0.0846P)^2^] wher Weighting scheme identified as calc PLAT_420 Alert C D-H without acceptor N6 - H06A ? General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 27.50 From the CIF: _reflns_number_total 3061 Count of symmetry unique reflns 3061 Completeness (_total/calc) 100.00% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present yes WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check
The preparation of (I) were carried out according to literature methods with minor changes (Ohgo et al., 1996). Crystals were obtained by recrystallization from ethanol/hexane.
The H atoms were refined using a riding model. The positional parameters of the H atoms were constrained to have C—H distances of 0.96 Å for primary, 0.97 Å for secondary, and 0.93 Å for aromatic. H-atom U values were constrained to 1.2 times the Ueq of the atoms to which they are attached (1.5 for methyl groups). The absolute configuration of (I) was set by reference to the known absolute configurations of the chiral amino ligands. There were no Friedel pairs in the measured data.
Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1992a); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1992b); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP (Johnson, 1965); software used to prepare material for publication: SHELXL97.
[Co(C4H7N2O2)2(C5H10NO)(C8H11N)] | F(000) = 540 |
Mr = 510.48 | Dx = 1.325 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.8987 (13) Å | Cell parameters from 25 reflections |
b = 14.3050 (16) Å | θ = 12.5–15.0° |
c = 10.1286 (11) Å | µ = 0.71 mm−1 |
β = 97.096 (9)° | T = 298 K |
V = 1279.5 (3) Å3 | Prismatic, red |
Z = 2 | 0.20 × 0.10 × 0.05 mm |
Rigaku AFC5 diffractometer | 2589 reflections with I > 2σ(I) |
Radiation source: rotating anode | Rint = 0.000 |
Graphite monochromator | θmax = 27.5°, θmin = 2.0° |
ω/2θ scans | h = 0→11 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→18 |
Tmin = 0.871, Tmax = 0.965 | l = −13→13 |
3061 measured reflections | 3 standard reflections every 100 reflections |
3061 independent reflections | intensity decay: none |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.122 | H-atom parameters constrained |
S = 1.02 | Calculated w = 1/[σ2(Fo2) + (0.0846P)2] where P = (Fo2 + 2Fc2)/3 |
3061 reflections | (Δ/σ)max < 0.001 |
309 parameters | Δρmax = 0.83 e Å−3 |
0 restraints | Δρmin = −0.48 e Å−3 |
[Co(C4H7N2O2)2(C5H10NO)(C8H11N)] | V = 1279.5 (3) Å3 |
Mr = 510.48 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 8.8987 (13) Å | µ = 0.71 mm−1 |
b = 14.3050 (16) Å | T = 298 K |
c = 10.1286 (11) Å | 0.20 × 0.10 × 0.05 mm |
β = 97.096 (9)° |
Rigaku AFC5 diffractometer | 2589 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.000 |
Tmin = 0.871, Tmax = 0.965 | 3 standard reflections every 100 reflections |
3061 measured reflections | intensity decay: none |
3061 independent reflections |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.122 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.83 e Å−3 |
3061 reflections | Δρmin = −0.48 e Å−3 |
309 parameters |
Experimental. Bis(dimethylglyoximato)[2,2-(dimethylcarbamoyl)ethyl] [(R)-1-phenylethylamine]cobalt(III) The preparation of the series of N-substituted cobaloxime complexes was basically carried out according to the literature methods with minor change·(Ohgo et al., 1996) The crystal were obtained by slow evaporation from ethanol/hexane. |
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. |
x | y | z | Uiso*/Ueq | ||
Co1 | 0.23975 (5) | −0.0004 (5) | 0.06825 (5) | 0.03753 (15) | |
O1 | 0.3063 (4) | −0.1065 (3) | −0.1544 (4) | 0.0684 (11) | |
H01 | 0.3884 | −0.0616 | −0.1158 | 0.082* | |
O2 | −0.0314 (4) | 0.0012 (5) | 0.1904 (3) | 0.0693 (9) | |
O3 | 0.1719 (4) | 0.1073 (3) | 0.2890 (3) | 0.0686 (10) | |
H03 | 0.0896 | 0.0644 | 0.2492 | 0.082* | |
O4 | 0.5067 (3) | 0.0033 (5) | −0.0605 (3) | 0.0662 (8) | |
O5 | −0.1023 (6) | 0.2371 (4) | −0.2033 (5) | 0.0918 (15) | |
N1 | 0.2041 (5) | −0.0878 (3) | −0.0702 (5) | 0.0447 (10) | |
N2 | 0.0420 (4) | −0.0343 (3) | 0.0925 (4) | 0.0490 (9) | |
N3 | 0.2743 (6) | 0.0895 (4) | 0.2055 (5) | 0.0509 (11) | |
N4 | 0.4345 (4) | 0.0381 (3) | 0.0387 (4) | 0.0494 (9) | |
N5 | 0.0416 (6) | 0.1771 (5) | −0.3478 (5) | 0.0812 (16) | |
N6 | 0.3110 (6) | −0.1056 (4) | 0.2008 (6) | 0.0629 (15) | |
H06A | 0.2679 | −0.0942 | 0.2750 | 0.076* | |
H06B | 0.2690 | −0.1588 | 0.1660 | 0.076* | |
C1 | 0.0733 (6) | −0.1273 (4) | −0.0864 (6) | 0.0520 (11) | |
C2 | −0.0239 (5) | −0.0962 (4) | 0.0119 (5) | 0.0516 (11) | |
C3 | 0.4012 (7) | 0.1340 (4) | 0.2141 (6) | 0.0583 (13) | |
C4 | 0.4968 (6) | 0.1047 (4) | 0.1148 (6) | 0.0565 (12) | |
C5 | 0.0235 (8) | −0.1939 (5) | −0.1949 (7) | 0.082 (2) | |
H5A | −0.0557 | −0.1661 | −0.2551 | 0.123* | |
H5B | −0.0137 | −0.2499 | −0.1579 | 0.123* | |
H5C | 0.1075 | −0.2090 | −0.2420 | 0.123* | |
C6 | −0.1826 (6) | −0.1312 (5) | 0.0181 (8) | 0.083 (2) | |
H6A | −0.2194 | −0.1611 | −0.0644 | 0.125* | |
H6B | −0.2472 | −0.0795 | 0.0329 | 0.125* | |
H6C | −0.1822 | −0.1752 | 0.0896 | 0.125* | |
C7 | 0.4475 (10) | 0.2073 (6) | 0.3181 (8) | 0.095 (2) | |
H7A | 0.4641 | 0.2656 | 0.2754 | 0.142* | |
H7B | 0.5392 | 0.1881 | 0.3713 | 0.142* | |
H7C | 0.3687 | 0.2148 | 0.3740 | 0.142* | |
C8 | 0.6471 (7) | 0.1470 (5) | 0.0981 (8) | 0.084 (2) | |
H8A | 0.7264 | 0.1102 | 0.1454 | 0.126* | |
H8B | 0.6516 | 0.2095 | 0.1328 | 0.126* | |
H8C | 0.6597 | 0.1485 | 0.0053 | 0.126* | |
C9 | 0.1624 (7) | 0.1007 (4) | −0.0599 (6) | 0.0531 (14) | |
H9A | 0.1617 | 0.1582 | −0.0092 | 0.064* | |
H9B | 0.2369 | 0.1088 | −0.1213 | 0.064* | |
C10 | 0.0104 (6) | 0.0930 (4) | −0.1423 (6) | 0.0581 (12) | |
H10A | −0.0678 | 0.0898 | −0.0837 | 0.070* | |
H10B | 0.0067 | 0.0356 | −0.1936 | 0.070* | |
C11 | −0.0212 (6) | 0.1745 (4) | −0.2355 (5) | 0.0563 (13) | |
C12 | 0.0138 (12) | 0.2548 (9) | −0.4355 (9) | 0.157 (5) | |
H12A | −0.0765 | 0.2437 | −0.4956 | 0.235* | |
H12B | 0.0980 | 0.2628 | −0.4852 | 0.235* | |
H12C | 0.0012 | 0.3103 | −0.3846 | 0.235* | |
C13 | 0.1366 (10) | 0.1020 (9) | −0.3919 (7) | 0.114 (3) | |
H13A | 0.2342 | 0.1268 | −0.4041 | 0.171* | |
H13B | 0.0893 | 0.0767 | −0.4745 | 0.171* | |
H13C | 0.1483 | 0.0536 | −0.3259 | 0.171* | |
C20 | 0.4746 (6) | −0.1275 (4) | 0.2457 (6) | 0.0559 (13) | |
H20 | 0.5341 | −0.1088 | 0.1748 | 0.067* | |
C21 | 0.5321 (5) | −0.0738 (4) | 0.3693 (4) | 0.0492 (10) | |
C22 | 0.6699 (7) | −0.0306 (5) | 0.3788 (8) | 0.087 (2) | |
H22 | 0.7252 | −0.0324 | 0.3067 | 0.105* | |
C23 | 0.7297 (10) | 0.0166 (8) | 0.4953 (13) | 0.128 (4) | |
H23 | 0.8234 | 0.0460 | 0.4993 | 0.154* | |
C24 | 0.6527 (14) | 0.0194 (10) | 0.6001 (11) | 0.144 (5) | |
H24 | 0.6934 | 0.0500 | 0.6773 | 0.173* | |
C25 | 0.5185 (12) | −0.0212 (8) | 0.5945 (7) | 0.112 (4) | |
H25 | 0.4649 | −0.0178 | 0.6676 | 0.135* | |
C26 | 0.4553 (7) | −0.0696 (6) | 0.4800 (6) | 0.083 (2) | |
H26 | 0.3617 | −0.0988 | 0.4787 | 0.100* | |
C27 | 0.4963 (12) | −0.2332 (5) | 0.2690 (9) | 0.113 (3) | |
H27A | 0.6021 | −0.2467 | 0.2907 | 0.170* | |
H27B | 0.4574 | −0.2664 | 0.1897 | 0.170* | |
H27C | 0.4427 | −0.2524 | 0.3411 | 0.170* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Co1 | 0.0378 (2) | 0.0401 (2) | 0.0339 (2) | 0.0007 (3) | 0.00110 (15) | 0.0006 (3) |
O1 | 0.073 (2) | 0.068 (3) | 0.068 (3) | 0.0005 (19) | 0.0250 (19) | −0.023 (2) |
O2 | 0.0573 (17) | 0.085 (2) | 0.071 (2) | 0.000 (3) | 0.0286 (15) | −0.004 (4) |
O3 | 0.083 (2) | 0.079 (3) | 0.0441 (19) | 0.008 (2) | 0.0120 (17) | −0.0153 (19) |
O4 | 0.0540 (16) | 0.073 (2) | 0.077 (2) | 0.005 (3) | 0.0276 (15) | −0.003 (3) |
O5 | 0.098 (3) | 0.076 (3) | 0.097 (3) | 0.041 (3) | −0.005 (3) | −0.002 (3) |
N1 | 0.045 (2) | 0.045 (2) | 0.044 (2) | 0.0074 (18) | 0.0025 (17) | −0.0048 (17) |
N2 | 0.0421 (18) | 0.058 (2) | 0.048 (2) | 0.0009 (16) | 0.0082 (16) | 0.0021 (17) |
N3 | 0.063 (3) | 0.052 (2) | 0.036 (2) | 0.003 (2) | 0.0026 (19) | 0.0016 (19) |
N4 | 0.0427 (18) | 0.052 (2) | 0.053 (2) | 0.0022 (16) | 0.0055 (16) | 0.0074 (18) |
N5 | 0.081 (3) | 0.117 (5) | 0.044 (2) | 0.009 (3) | 0.005 (2) | 0.018 (3) |
N6 | 0.058 (3) | 0.057 (3) | 0.068 (3) | −0.013 (2) | −0.015 (2) | 0.026 (3) |
C1 | 0.051 (3) | 0.040 (2) | 0.061 (3) | 0.003 (2) | −0.007 (2) | −0.002 (2) |
C2 | 0.043 (2) | 0.046 (2) | 0.063 (3) | −0.0010 (19) | −0.003 (2) | 0.007 (2) |
C3 | 0.071 (4) | 0.047 (3) | 0.051 (3) | −0.003 (3) | −0.015 (3) | −0.003 (2) |
C4 | 0.052 (2) | 0.046 (3) | 0.068 (3) | −0.010 (2) | −0.006 (2) | 0.006 (2) |
C5 | 0.080 (4) | 0.065 (4) | 0.094 (5) | −0.004 (3) | −0.017 (4) | −0.036 (4) |
C6 | 0.041 (3) | 0.077 (4) | 0.130 (6) | −0.009 (3) | 0.003 (3) | −0.004 (4) |
C7 | 0.116 (6) | 0.077 (5) | 0.084 (5) | −0.017 (4) | −0.017 (4) | −0.033 (4) |
C8 | 0.058 (3) | 0.074 (4) | 0.117 (6) | −0.024 (3) | 0.001 (3) | 0.007 (4) |
C9 | 0.060 (3) | 0.046 (3) | 0.050 (3) | 0.000 (2) | −0.007 (2) | 0.004 (2) |
C10 | 0.051 (2) | 0.064 (3) | 0.058 (3) | 0.012 (2) | 0.002 (2) | 0.014 (3) |
C11 | 0.055 (3) | 0.059 (3) | 0.052 (3) | 0.010 (2) | −0.009 (2) | 0.001 (2) |
C12 | 0.149 (9) | 0.198 (12) | 0.113 (7) | −0.039 (9) | −0.029 (6) | 0.103 (8) |
C13 | 0.111 (6) | 0.172 (10) | 0.061 (4) | 0.018 (6) | 0.015 (4) | −0.027 (5) |
C20 | 0.059 (3) | 0.053 (3) | 0.053 (3) | 0.008 (2) | −0.007 (2) | 0.002 (2) |
C21 | 0.050 (2) | 0.052 (2) | 0.044 (2) | 0.009 (2) | −0.0034 (18) | 0.006 (2) |
C22 | 0.056 (3) | 0.103 (6) | 0.099 (5) | −0.008 (3) | −0.005 (3) | −0.004 (4) |
C23 | 0.092 (5) | 0.117 (9) | 0.160 (9) | −0.015 (6) | −0.052 (6) | −0.021 (8) |
C24 | 0.140 (9) | 0.171 (13) | 0.105 (7) | 0.039 (9) | −0.049 (6) | −0.053 (9) |
C25 | 0.144 (8) | 0.140 (10) | 0.051 (3) | 0.044 (7) | 0.004 (4) | −0.009 (4) |
C26 | 0.076 (4) | 0.116 (6) | 0.059 (3) | 0.004 (4) | 0.017 (3) | 0.008 (4) |
C27 | 0.141 (8) | 0.059 (4) | 0.122 (7) | 0.017 (4) | −0.055 (6) | −0.018 (5) |
Co1—N2 | 1.871 (4) | C6—H6C | 0.960 |
Co1—N1 | 1.876 (5) | C7—H7A | 0.960 |
Co1—N4 | 1.878 (4) | C7—H7B | 0.960 |
Co1—N3 | 1.891 (5) | C7—H7C | 0.960 |
Co1—C9 | 2.008 (6) | C8—H8A | 0.960 |
Co1—N6 | 2.065 (5) | C8—H8B | 0.960 |
O1—N1 | 1.348 (6) | C8—H8C | 0.960 |
O1—H01 | 1.014 | C9—C10 | 1.503 (7) |
O2—N2 | 1.352 (5) | C9—H9A | 0.970 |
O2—H03 | 1.474 | C9—H9B | 0.970 |
O3—N3 | 1.342 (6) | C10—C11 | 1.505 (8) |
O3—H03 | 1.001 | C10—H10A | 0.970 |
O4—N4 | 1.352 (5) | C10—H10B | 0.970 |
O4—H01 | 1.462 | C12—H12A | 0.960 |
O5—C11 | 1.220 (7) | C12—H12B | 0.960 |
N1—C1 | 1.286 (7) | C12—H12C | 0.960 |
N2—C2 | 1.295 (6) | C13—H13A | 0.960 |
N3—C3 | 1.290 (8) | C13—H13B | 0.960 |
N4—C4 | 1.305 (7) | C13—H13C | 0.960 |
N5—C11 | 1.328 (8) | C20—C21 | 1.503 (7) |
N5—C12 | 1.425 (11) | C20—C27 | 1.539 (9) |
N5—C13 | 1.470 (11) | C20—H20 | 0.980 |
N6—C20 | 1.504 (7) | C21—C22 | 1.366 (8) |
N6—H06A | 0.900 | C21—C26 | 1.385 (8) |
N6—H06B | 0.900 | C22—C23 | 1.406 (13) |
C1—C2 | 1.467 (8) | C22—H22 | 0.930 |
C1—C5 | 1.481 (8) | C23—C24 | 1.333 (15) |
C2—C6 | 1.506 (7) | C23—H23 | 0.930 |
C3—C4 | 1.456 (9) | C24—C25 | 1.323 (15) |
C3—C7 | 1.507 (8) | C24—H24 | 0.930 |
C4—C8 | 1.497 (7) | C25—C26 | 1.407 (11) |
C5—H5A | 0.960 | C25—H25 | 0.930 |
C5—H5B | 0.960 | C26—H26 | 0.930 |
C5—H5C | 0.960 | C27—H27A | 0.960 |
C6—H6A | 0.960 | C27—H27B | 0.960 |
C6—H6B | 0.960 | C27—H27C | 0.960 |
N2—Co1—N1 | 81.4 (2) | C3—C7—H7C | 109.5 |
N2—Co1—N4 | 177.3 (2) | H7A—C7—H7C | 109.5 |
N1—Co1—N4 | 98.7 (2) | H7B—C7—H7C | 109.5 |
N2—Co1—N3 | 98.6 (2) | C4—C8—H8A | 109.5 |
N1—Co1—N3 | 178.9 (2) | C4—C8—H8B | 109.5 |
N4—Co1—N3 | 81.3 (2) | H8A—C8—H8B | 109.5 |
N2—Co1—C9 | 91.1 (2) | C4—C8—H8C | 109.5 |
N1—Co1—C9 | 89.1 (2) | H8A—C8—H8C | 109.5 |
N4—Co1—C9 | 86.3 (2) | H8B—C8—H8C | 109.5 |
N3—Co1—C9 | 89.8 (3) | C10—C9—Co1 | 121.3 (4) |
N2—Co1—N6 | 86.8 (2) | C10—C9—H9A | 107.0 |
N1—Co1—N6 | 90.6 (2) | Co1—C9—H9A | 107.0 |
N4—Co1—N6 | 95.9 (2) | C10—C9—H9B | 107.0 |
N3—Co1—N6 | 90.5 (2) | Co1—C9—H9B | 107.0 |
C9—Co1—N6 | 177.8 (3) | H9A—C9—H9B | 106.7 |
N1—O1—H01 | 98.1 | C9—C10—C11 | 112.1 (5) |
N2—O2—H03 | 97.6 | C9—C10—H10A | 109.2 |
N3—O3—H03 | 98.6 | C11—C10—H10A | 109.2 |
N4—O4—H01 | 97.6 | C9—C10—H10B | 109.2 |
C1—N1—O1 | 120.2 (5) | C11—C10—H10B | 109.2 |
C1—N1—Co1 | 117.1 (4) | H10A—C10—H10B | 107.9 |
O1—N1—Co1 | 122.7 (4) | O5—C11—N5 | 122.3 (6) |
C2—N2—O2 | 119.8 (4) | O5—C11—C10 | 118.1 (5) |
C2—N2—Co1 | 117.1 (3) | N5—C11—C10 | 119.6 (5) |
O2—N2—Co1 | 123.1 (3) | N5—C12—H12A | 109.5 |
C3—N3—O3 | 121.4 (5) | N5—C12—H12B | 109.5 |
C3—N3—Co1 | 116.5 (4) | H12A—C12—H12B | 109.5 |
O3—N3—Co1 | 122.1 (4) | N5—C12—H12C | 109.5 |
C4—N4—O4 | 120.1 (4) | H12A—C12—H12C | 109.5 |
C4—N4—Co1 | 116.9 (4) | H12B—C12—H12C | 109.5 |
O4—N4—Co1 | 122.9 (3) | N5—C13—H13A | 109.5 |
C11—N5—C12 | 119.7 (8) | N5—C13—H13B | 109.5 |
C11—N5—C13 | 123.9 (7) | H13A—C13—H13B | 109.5 |
C12—N5—C13 | 116.3 (7) | N5—C13—H13C | 109.5 |
C20—N6—Co1 | 123.8 (4) | H13A—C13—H13C | 109.5 |
C20—N6—H06A | 106.4 | H13B—C13—H13C | 109.5 |
Co1—N6—H06A | 106.4 | C21—C20—N6 | 111.3 (5) |
C20—N6—H06B | 106.4 | C21—C20—C27 | 110.5 (5) |
Co1—N6—H06B | 106.4 | N6—C20—C27 | 110.4 (6) |
H06A—N6—H06B | 106.5 | C21—C20—H20 | 108.2 |
N1—C1—C2 | 112.4 (5) | N6—C20—H20 | 108.2 |
N1—C1—C5 | 124.1 (6) | C27—C20—H20 | 108.2 |
C2—C1—C5 | 123.4 (5) | C22—C21—C26 | 116.9 (6) |
N2—C2—C1 | 112.1 (4) | C22—C21—C20 | 120.0 (5) |
N2—C2—C6 | 123.7 (5) | C26—C21—C20 | 123.1 (5) |
C1—C2—C6 | 124.2 (5) | C21—C22—C23 | 121.3 (8) |
N3—C3—C4 | 113.1 (5) | C21—C22—H22 | 119.3 |
N3—C3—C7 | 123.5 (6) | C23—C22—H22 | 119.3 |
C4—C3—C7 | 123.4 (6) | C24—C23—C22 | 120.2 (9) |
N4—C4—C3 | 112.1 (4) | C24—C23—H23 | 119.9 |
N4—C4—C8 | 123.3 (6) | C22—C23—H23 | 119.9 |
C3—C4—C8 | 124.6 (5) | C25—C24—C23 | 120.2 (9) |
C1—C5—H5A | 109.5 | C25—C24—H24 | 119.9 |
C1—C5—H5B | 109.5 | C23—C24—H24 | 119.9 |
H5A—C5—H5B | 109.5 | C24—C25—C26 | 121.2 (8) |
C1—C5—H5C | 109.5 | C24—C25—H25 | 119.4 |
H5A—C5—H5C | 109.5 | C26—C25—H25 | 119.4 |
H5B—C5—H5C | 109.5 | C21—C26—C25 | 120.1 (7) |
C2—C6—H6A | 109.5 | C21—C26—H26 | 119.9 |
C2—C6—H6B | 109.5 | C25—C26—H26 | 119.9 |
H6A—C6—H6B | 109.5 | C20—C27—H27A | 109.5 |
C2—C6—H6C | 109.5 | C20—C27—H27B | 109.5 |
H6A—C6—H6C | 109.5 | H27A—C27—H27B | 109.5 |
H6B—C6—H6C | 109.5 | C20—C27—H27C | 109.5 |
C3—C7—H7A | 109.5 | H27A—C27—H27C | 109.5 |
C3—C7—H7B | 109.5 | H27B—C27—H27C | 109.5 |
H7A—C7—H7B | 109.5 | ||
N2—Co1—N1—C1 | 0.6 (4) | Co1—N2—C2—C6 | 179.9 (5) |
N4—Co1—N1—C1 | −176.7 (4) | N1—C1—C2—N2 | 1.2 (7) |
C9—Co1—N1—C1 | −90.6 (5) | C5—C1—C2—N2 | −176.6 (5) |
N6—Co1—N1—C1 | 87.3 (4) | N1—C1—C2—C6 | −179.5 (5) |
N2—Co1—N1—O1 | 177.6 (4) | C5—C1—C2—C6 | 2.7 (9) |
N4—Co1—N1—O1 | 0.3 (4) | Co1—N3—C3—C4 | −0.8 (6) |
C9—Co1—N1—O1 | 86.4 (4) | O3—N3—C3—C7 | 1.2 (9) |
N6—Co1—N1—O1 | −95.7 (4) | Co1—N3—C3—C7 | −179.5 (5) |
N1—Co1—N2—C2 | 0.1 (4) | O4—N4—C4—C3 | 179.0 (4) |
N3—Co1—N2—C2 | 179.0 (4) | Co1—N4—C4—C3 | 2.3 (6) |
C9—Co1—N2—C2 | 89.0 (4) | O4—N4—C4—C8 | 0.7 (8) |
N6—Co1—N2—C2 | −91.0 (4) | Co1—N4—C4—C8 | −176.1 (4) |
N1—Co1—N2—O2 | 178.7 (5) | N3—C3—C4—N4 | −0.9 (7) |
N3—Co1—N2—O2 | −2.4 (5) | C7—C3—C4—N4 | 177.8 (5) |
C9—Co1—N2—O2 | −92.4 (5) | N3—C3—C4—C8 | 177.4 (5) |
N6—Co1—N2—O2 | 87.6 (5) | C7—C3—C4—C8 | −3.9 (9) |
N2—Co1—N3—C3 | −175.7 (4) | N2—Co1—C9—C10 | −28.3 (5) |
N4—Co1—N3—C3 | 1.6 (4) | N1—Co1—C9—C10 | 53.1 (5) |
C9—Co1—N3—C3 | −84.7 (4) | N4—Co1—C9—C10 | 151.8 (5) |
N6—Co1—N3—C3 | 97.4 (5) | N3—Co1—C9—C10 | −126.9 (5) |
N2—Co1—N3—O3 | 3.5 (4) | Co1—C9—C10—C11 | −177.4 (4) |
N4—Co1—N3—O3 | −179.2 (4) | C12—N5—C11—O5 | −0.4 (10) |
C9—Co1—N3—O3 | 94.6 (5) | C13—N5—C11—O5 | −178.3 (7) |
N6—Co1—N3—O3 | −83.3 (4) | C12—N5—C11—C10 | −179.1 (6) |
N1—Co1—N4—C4 | 176.7 (4) | C13—N5—C11—C10 | 3.0 (10) |
N3—Co1—N4—C4 | −2.2 (4) | C9—C10—C11—O5 | −100.0 (7) |
C9—Co1—N4—C4 | 88.2 (4) | C9—C10—C11—N5 | 78.8 (7) |
N6—Co1—N4—C4 | −91.8 (4) | Co1—N6—C20—C21 | 91.0 (6) |
N1—Co1—N4—O4 | 0.1 (4) | Co1—N6—C20—C27 | −145.9 (6) |
N3—Co1—N4—O4 | −178.8 (4) | N6—C20—C21—C22 | −135.3 (6) |
C9—Co1—N4—O4 | −88.4 (4) | C27—C20—C21—C22 | 101.7 (8) |
N6—Co1—N4—O4 | 91.6 (4) | N6—C20—C21—C26 | 48.4 (7) |
N2—Co1—N6—C20 | −178.3 (5) | C27—C20—C21—C26 | −74.7 (8) |
N1—Co1—N6—C20 | 100.4 (5) | C26—C21—C22—C23 | −0.6 (11) |
N4—Co1—N6—C20 | 1.6 (5) | C20—C21—C22—C23 | −177.2 (7) |
N3—Co1—N6—C20 | −79.6 (5) | C21—C22—C23—C24 | 0.6 (16) |
O1—N1—C1—C2 | −178.2 (4) | C22—C23—C24—C25 | −1 (2) |
Co1—N1—C1—C2 | −1.2 (6) | C23—C24—C25—C26 | 1.3 (19) |
O1—N1—C1—C5 | −0.4 (8) | C22—C21—C26—C25 | 0.9 (10) |
Co1—N1—C1—C5 | 176.6 (5) | C20—C21—C26—C25 | 177.4 (6) |
O2—N2—C2—C1 | −179.3 (5) | C24—C25—C26—C21 | −1.3 (14) |
Co1—N2—C2—C1 | −0.7 (5) | C9—C10—C11—N5 | 78.8 (7) |
O2—N2—C2—C6 | 1.3 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H01···O4 | 1.01 | 1.46 | 2.476 (6) | 180 |
O3—H03···O2 | 1.00 | 1.47 | 2.475 (7) | 180 |
N6—H06B···O5i | 0.90 | 2.17 | 2.919 (7) | 141 |
Symmetry code: (i) −x, y−1/2, −z. |
Experimental details
Crystal data | |
Chemical formula | [Co(C4H7N2O2)2(C5H10NO)(C8H11N)] |
Mr | 510.48 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 298 |
a, b, c (Å) | 8.8987 (13), 14.3050 (16), 10.1286 (11) |
β (°) | 97.096 (9) |
V (Å3) | 1279.5 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.71 |
Crystal size (mm) | 0.20 × 0.10 × 0.05 |
Data collection | |
Diffractometer | Rigaku AFC5 diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.871, 0.965 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3061, 3061, 2589 |
Rint | 0.000 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.122, 1.02 |
No. of reflections | 3061 |
No. of parameters | 309 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.83, −0.48 |
Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1992a), MSC/AFC Diffractometer Control Software, TEXSAN (Molecular Structure Corporation, 1992b), SAPI91 (Fan, 1991), SHELXL97 (Sheldrick, 1997), ORTEP (Johnson, 1965), SHELXL97.
Co1—N2 | 1.871 (4) | Co1—N3 | 1.891 (5) |
Co1—N1 | 1.876 (5) | Co1—C9 | 2.008 (6) |
Co1—N4 | 1.878 (4) | Co1—N6 | 2.065 (5) |
Co1—C9—C10—C11 | −177.4 (4) | C9—C10—C11—N5 | 78.8 (7) |
C9—C10—C11—O5 | −100.0 (7) | C9—C10—C11—N5 | 78.8 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H01···O4 | 1.01 | 1.46 | 2.476 (6) | 180 |
O3—H03···O2 | 1.00 | 1.47 | 2.475 (7) | 180 |
N6—H06B···O5i | 0.90 | 2.17 | 2.919 (7) | 141 |
Symmetry code: (i) −x, y−1/2, −z. |
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A series of cobaloxime complexes containing the 2-(N-substituted-carbamoyl)ethyl group were synthesized to analyze the relationship between the void space and the intermolecular hydrogen bond (Ohgo et al., 1996, 2001), since the 2-carbamoylethyl group has both the hydrogen-donor (NH) and acceptor (C═O) atoms. In the course of the studies on photoracemization and (β–α) photoisomerization in a series of cobaloxime complexes, the 2-substituted-carbamoylethyl groups in some cobaloxime complexes were found to be isomerized to the 1-substituted-carbamoylethyl groups. Futhermore, asymmetric induction up to 69% ee was observed in the photoreaction of the above complexes. In terms of this asymmetric induction, the hydrogen bonds of the reactive groups may play a role. The title compound, (I), was synthesized to make clear the role of hydrogen bonds in the solid-state photoreaction, systematically.
The crystal structures of (I) viewed along the a axis is shown in Fig. 1 and Fig. 2 shows the molecule of (I) with the numbering of the atoms. The trans conformations around Co—C9—C10—N5 and C10—C11—N5—C12 indicate that the 2-(N,N-dimethylcarbamoyl)ethyl group lies perpendicular to the cobaloxime plane·The torsion angle C9—C10—C11—N5, 78.8°, is almost the same angle as that in bis(dimethylglyoximato)[2-(methylcarbamoyl)ethyl][methyl (S)-phenylalaninate]cobalt(III), 75.0° (Ohgo et al., 2000). The hydrogen bonds in (I) are given in Table 2. The N6 atom of the (R)-1-phenylethylamine moiety is hydrogen bonded to the O5 atom of the 2-(N,N-dimethylcarbamoyl)ethyl moiety of the neighboring molecule at (-x, y - 1/2, -z). Further investigation on the correlation between the structure and the reactivity is in progress.