The title Schiff base compound, [Co(C
16H
24N
2O)
2(NCS)
2], is centrosymmetric with the octahedrally coordinated Co
II atom lying on an inversion center. The Co atom is coordinated by two N atoms and two O atoms from two 2-[(3-cyclohexylaminopropylimino)methyl]phenolate Schiff base ligands and another two N atoms from two thiocyanate anions. In the crystal structure, the molecules are linked by N—H
S intermolecular hydrogen bonds, forming a polymer extending in the
b-axis direction.
Supporting information
CCDC reference: 270555
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.010 Å
- R factor = 0.061
- wR factor = 0.192
- Data-to-parameter ratio = 14.5
checkCIF/PLATON results
No syntax errors found
Alert level C
RINTA01_ALERT_3_C The value of Rint is greater than 0.10
Rint given 0.101
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.10
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 45 Perc.
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.96
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for N3
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C13
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C11
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C17
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 10
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
9 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
4 ALERT type 2 Indicator that the structure model may be wrong or deficient
5 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1997); software used to prepare material for publication: SHELXTL.
Bis{2-[3-(cyclohexylammonio)propyliminomethyl]phenolato}dithiocyanatocobalt(II)
top
Crystal data top
[Co(C16H24N2O)2(NCS)2] | F(000) = 738 |
Mr = 695.83 | Dx = 1.317 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 755 reflections |
a = 10.912 (7) Å | θ = 2.8–23.4° |
b = 7.797 (5) Å | µ = 0.65 mm−1 |
c = 20.777 (13) Å | T = 298 K |
β = 96.899 (13)° | Block, brown |
V = 1754.9 (19) Å3 | 0.29 × 0.17 × 0.11 mm |
Z = 2 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 2975 independent reflections |
Radiation source: fine-focus sealed tube | 1337 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.101 |
ω scans | θmax = 25.0°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→12 |
Tmin = 0.835, Tmax = 0.932 | k = −9→7 |
7131 measured reflections | l = −12→24 |
Refinement top
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)] = 0.061 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.192 | H-atom parameters constrained |
S = 0.84 | w = 1/[σ2(Fo2) + (0.0889P)2] where P = (Fo2 + 2Fc2)/3 |
2975 reflections | (Δ/σ)max < 0.001 |
205 parameters | Δρmax = 0.54 e Å−3 |
0 restraints | Δρmin = −0.55 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
Co1 | 0.0000 | 0.5000 | 0.0000 | 0.0459 (4) | |
N1 | 0.0966 (4) | 0.6469 (7) | 0.0733 (3) | 0.0546 (14) | |
N2 | 0.2901 (4) | 0.7563 (6) | −0.0521 (2) | 0.0529 (13) | |
H2A | 0.2918 | 0.8703 | −0.0586 | 0.064* | |
H2B | 0.2110 | 0.7221 | −0.0604 | 0.064* | |
N3 | −0.1559 (5) | 0.6567 (7) | 0.0106 (3) | 0.0657 (16) | |
O1 | −0.0528 (3) | 0.3418 (5) | 0.0693 (2) | 0.0579 (11) | |
S1 | −0.32274 (16) | 0.8260 (2) | 0.08022 (9) | 0.0703 (6) | |
C1 | 0.1229 (5) | 0.5931 (10) | 0.1323 (4) | 0.0616 (19) | |
H1 | 0.1623 | 0.6711 | 0.1617 | 0.074* | |
C2 | 0.0982 (5) | 0.4268 (9) | 0.1576 (3) | 0.0556 (17) | |
C3 | 0.0146 (5) | 0.3074 (9) | 0.1256 (3) | 0.0553 (17) | |
C4 | 0.0014 (5) | 0.1506 (9) | 0.1567 (3) | 0.0600 (18) | |
H4 | −0.0517 | 0.0684 | 0.1365 | 0.072* | |
C5 | 0.0638 (6) | 0.1150 (11) | 0.2158 (4) | 0.071 (2) | |
H5 | 0.0530 | 0.0094 | 0.2351 | 0.085* | |
C6 | 0.1439 (7) | 0.2353 (12) | 0.2477 (4) | 0.078 (2) | |
H6 | 0.1859 | 0.2115 | 0.2883 | 0.094* | |
C7 | 0.1591 (6) | 0.3860 (11) | 0.2186 (3) | 0.0664 (19) | |
H7 | 0.2124 | 0.4665 | 0.2398 | 0.080* | |
C8 | 0.1342 (6) | 0.8239 (9) | 0.0603 (3) | 0.0641 (19) | |
H8A | 0.1063 | 0.8997 | 0.0926 | 0.077* | |
H8B | 0.0944 | 0.8593 | 0.0182 | 0.077* | |
C9 | 0.2738 (6) | 0.8425 (9) | 0.0616 (3) | 0.070 (2) | |
H9A | 0.2918 | 0.9594 | 0.0497 | 0.084* | |
H9B | 0.3120 | 0.8242 | 0.1056 | 0.084* | |
C10 | 0.3332 (6) | 0.7214 (9) | 0.0171 (3) | 0.0651 (19) | |
H10A | 0.4222 | 0.7342 | 0.0246 | 0.078* | |
H10B | 0.3133 | 0.6040 | 0.0273 | 0.078* | |
C11 | 0.3644 (5) | 0.6697 (8) | −0.1003 (3) | 0.0542 (16) | |
H11 | 0.3746 | 0.5484 | −0.0884 | 0.065* | |
C12 | 0.4911 (6) | 0.7513 (11) | −0.0965 (4) | 0.091 (3) | |
H12A | 0.5349 | 0.7346 | −0.0536 | 0.110* | |
H12B | 0.4826 | 0.8736 | −0.1043 | 0.110* | |
C13 | 0.5644 (7) | 0.6704 (13) | −0.1472 (4) | 0.107 (3) | |
H13A | 0.6432 | 0.7284 | −0.1463 | 0.128* | |
H13B | 0.5805 | 0.5510 | −0.1363 | 0.128* | |
C14 | 0.4983 (7) | 0.6813 (10) | −0.2128 (4) | 0.089 (2) | |
H14A | 0.5455 | 0.6227 | −0.2429 | 0.107* | |
H14B | 0.4905 | 0.8007 | −0.2258 | 0.107* | |
C15 | 0.3729 (7) | 0.6029 (12) | −0.2162 (4) | 0.094 (3) | |
H15A | 0.3811 | 0.4803 | −0.2088 | 0.113* | |
H15B | 0.3294 | 0.6201 | −0.2592 | 0.113* | |
C16 | 0.2984 (6) | 0.6803 (11) | −0.1664 (3) | 0.080 (2) | |
H16A | 0.2810 | 0.7996 | −0.1772 | 0.096* | |
H16B | 0.2202 | 0.6204 | −0.1678 | 0.096* | |
C17 | −0.2235 (6) | 0.7286 (8) | 0.0390 (3) | 0.0512 (16) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Co1 | 0.0364 (7) | 0.0519 (8) | 0.0518 (7) | −0.0032 (5) | 0.0147 (5) | −0.0059 (6) |
N1 | 0.042 (3) | 0.060 (4) | 0.065 (4) | −0.004 (2) | 0.020 (3) | −0.013 (3) |
N2 | 0.043 (3) | 0.050 (3) | 0.066 (4) | −0.005 (2) | 0.009 (3) | −0.007 (3) |
N3 | 0.051 (4) | 0.066 (4) | 0.081 (4) | 0.006 (3) | 0.012 (3) | −0.011 (3) |
O1 | 0.049 (3) | 0.065 (3) | 0.060 (3) | −0.014 (2) | 0.009 (2) | −0.002 (2) |
S1 | 0.0655 (12) | 0.0556 (12) | 0.0944 (14) | 0.0041 (8) | 0.0283 (10) | −0.0034 (10) |
C1 | 0.046 (4) | 0.083 (6) | 0.057 (5) | −0.001 (4) | 0.009 (3) | −0.028 (4) |
C2 | 0.042 (4) | 0.066 (5) | 0.062 (5) | −0.005 (3) | 0.017 (3) | −0.014 (4) |
C3 | 0.035 (4) | 0.072 (5) | 0.063 (4) | 0.009 (3) | 0.022 (3) | −0.010 (4) |
C4 | 0.046 (4) | 0.060 (5) | 0.076 (5) | 0.006 (3) | 0.020 (4) | 0.003 (4) |
C5 | 0.059 (5) | 0.083 (6) | 0.073 (5) | 0.015 (4) | 0.023 (4) | 0.018 (4) |
C6 | 0.067 (5) | 0.098 (7) | 0.071 (5) | 0.018 (5) | 0.014 (4) | 0.005 (5) |
C7 | 0.047 (4) | 0.093 (6) | 0.059 (5) | 0.005 (4) | 0.006 (3) | −0.012 (4) |
C8 | 0.071 (5) | 0.056 (5) | 0.069 (5) | −0.002 (3) | 0.024 (4) | −0.016 (4) |
C9 | 0.075 (5) | 0.064 (5) | 0.074 (5) | −0.023 (4) | 0.020 (4) | −0.008 (4) |
C10 | 0.050 (4) | 0.080 (5) | 0.065 (5) | −0.009 (3) | 0.007 (3) | −0.001 (4) |
C11 | 0.047 (4) | 0.046 (4) | 0.073 (5) | 0.003 (3) | 0.022 (3) | −0.001 (3) |
C12 | 0.043 (4) | 0.136 (8) | 0.097 (6) | −0.007 (4) | 0.018 (4) | −0.031 (5) |
C13 | 0.052 (5) | 0.158 (9) | 0.116 (7) | −0.012 (5) | 0.032 (5) | −0.042 (7) |
C14 | 0.082 (6) | 0.080 (6) | 0.113 (7) | −0.011 (4) | 0.046 (5) | −0.005 (5) |
C15 | 0.069 (5) | 0.132 (8) | 0.084 (6) | 0.006 (5) | 0.021 (4) | −0.027 (5) |
C16 | 0.058 (5) | 0.115 (7) | 0.071 (5) | 0.010 (4) | 0.021 (4) | −0.013 (5) |
C17 | 0.058 (4) | 0.038 (4) | 0.058 (4) | −0.003 (3) | 0.004 (3) | 0.000 (3) |
Geometric parameters (Å, º) top
Co1—O1 | 2.031 (4) | C7—H7 | 0.9300 |
Co1—O1i | 2.031 (4) | C8—C9 | 1.527 (9) |
Co1—N1i | 2.087 (5) | C8—H8A | 0.9700 |
Co1—N1 | 2.087 (5) | C8—H8B | 0.9700 |
Co1—N3i | 2.127 (6) | C9—C10 | 1.519 (9) |
Co1—N3 | 2.127 (6) | C9—H9A | 0.9700 |
N1—C1 | 1.296 (8) | C9—H9B | 0.9700 |
N1—C8 | 1.474 (8) | C10—H10A | 0.9700 |
N2—C10 | 1.485 (7) | C10—H10B | 0.9700 |
N2—C11 | 1.519 (7) | C11—C16 | 1.475 (8) |
N2—H2A | 0.9000 | C11—C12 | 1.515 (8) |
N2—H2B | 0.9000 | C11—H11 | 0.9800 |
N3—C17 | 1.144 (7) | C12—C13 | 1.533 (10) |
O1—C3 | 1.331 (7) | C12—H12A | 0.9700 |
S1—C17 | 1.645 (7) | C12—H12B | 0.9700 |
C1—C2 | 1.437 (9) | C13—C14 | 1.466 (10) |
C1—H1 | 0.9300 | C13—H13A | 0.9700 |
C2—C7 | 1.395 (9) | C13—H13B | 0.9700 |
C2—C3 | 1.413 (8) | C14—C15 | 1.492 (9) |
C3—C4 | 1.400 (9) | C14—H14A | 0.9700 |
C4—C5 | 1.359 (9) | C14—H14B | 0.9700 |
C4—H4 | 0.9300 | C15—C16 | 1.516 (9) |
C5—C6 | 1.394 (10) | C15—H15A | 0.9700 |
C5—H5 | 0.9300 | C15—H15B | 0.9700 |
C6—C7 | 1.341 (9) | C16—H16A | 0.9700 |
C6—H6 | 0.9300 | C16—H16B | 0.9700 |
| | | |
O1—Co1—O1i | 180.0 (2) | C9—C8—H8B | 109.1 |
O1—Co1—N1i | 91.3 (2) | H8A—C8—H8B | 107.8 |
O1i—Co1—N1i | 88.7 (2) | C10—C9—C8 | 115.4 (5) |
O1—Co1—N1 | 88.7 (2) | C10—C9—H9A | 108.4 |
O1i—Co1—N1 | 91.3 (2) | C8—C9—H9A | 108.4 |
N1i—Co1—N1 | 180.0 (2) | C10—C9—H9B | 108.4 |
O1—Co1—N3i | 91.3 (2) | C8—C9—H9B | 108.4 |
O1i—Co1—N3i | 88.7 (2) | H9A—C9—H9B | 107.5 |
N1i—Co1—N3i | 87.1 (2) | N2—C10—C9 | 111.5 (6) |
N1—Co1—N3i | 92.9 (2) | N2—C10—H10A | 109.3 |
O1—Co1—N3 | 88.7 (2) | C9—C10—H10A | 109.3 |
O1i—Co1—N3 | 91.3 (2) | N2—C10—H10B | 109.3 |
N1i—Co1—N3 | 92.9 (2) | C9—C10—H10B | 109.3 |
N1—Co1—N3 | 87.1 (2) | H10A—C10—H10B | 108.0 |
N3i—Co1—N3 | 180.0 (3) | C16—C11—C12 | 111.4 (6) |
C1—N1—C8 | 116.2 (6) | C16—C11—N2 | 110.4 (5) |
C1—N1—Co1 | 123.2 (5) | C12—C11—N2 | 109.6 (5) |
C8—N1—Co1 | 120.5 (4) | C16—C11—H11 | 108.5 |
C10—N2—C11 | 115.1 (5) | C12—C11—H11 | 108.5 |
C10—N2—H2A | 108.5 | N2—C11—H11 | 108.5 |
C11—N2—H2A | 108.5 | C11—C12—C13 | 109.9 (6) |
C10—N2—H2B | 108.5 | C11—C12—H12A | 109.7 |
C11—N2—H2B | 108.5 | C13—C12—H12A | 109.7 |
H2A—N2—H2B | 107.5 | C11—C12—H12B | 109.7 |
C17—N3—Co1 | 155.2 (5) | C13—C12—H12B | 109.7 |
C3—O1—Co1 | 124.8 (4) | H12A—C12—H12B | 108.2 |
N1—C1—C2 | 127.5 (6) | C14—C13—C12 | 112.1 (7) |
N1—C1—H1 | 116.3 | C14—C13—H13A | 109.2 |
C2—C1—H1 | 116.3 | C12—C13—H13A | 109.2 |
C7—C2—C3 | 119.2 (7) | C14—C13—H13B | 109.2 |
C7—C2—C1 | 116.6 (6) | C12—C13—H13B | 109.2 |
C3—C2—C1 | 124.1 (6) | H13A—C13—H13B | 107.9 |
O1—C3—C4 | 120.4 (6) | C13—C14—C15 | 111.4 (7) |
O1—C3—C2 | 122.6 (7) | C13—C14—H14A | 109.3 |
C4—C3—C2 | 117.0 (6) | C15—C14—H14A | 109.3 |
C5—C4—C3 | 121.9 (7) | C13—C14—H14B | 109.3 |
C5—C4—H4 | 119.1 | C15—C14—H14B | 109.3 |
C3—C4—H4 | 119.1 | H14A—C14—H14B | 108.0 |
C4—C5—C6 | 120.6 (7) | C14—C15—C16 | 111.6 (6) |
C4—C5—H5 | 119.7 | C14—C15—H15A | 109.3 |
C6—C5—H5 | 119.7 | C16—C15—H15A | 109.3 |
C7—C6—C5 | 118.7 (7) | C14—C15—H15B | 109.3 |
C7—C6—H6 | 120.7 | C16—C15—H15B | 109.3 |
C5—C6—H6 | 120.7 | H15A—C15—H15B | 108.0 |
C6—C7—C2 | 122.5 (7) | C11—C16—C15 | 111.8 (6) |
C6—C7—H7 | 118.7 | C11—C16—H16A | 109.3 |
C2—C7—H7 | 118.7 | C15—C16—H16A | 109.3 |
N1—C8—C9 | 112.6 (5) | C11—C16—H16B | 109.3 |
N1—C8—H8A | 109.1 | C15—C16—H16B | 109.3 |
C9—C8—H8A | 109.1 | H16A—C16—H16B | 107.9 |
N1—C8—H8B | 109.1 | N3—C17—S1 | 178.1 (6) |
Symmetry code: (i) −x, −y+1, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2B···O1i | 0.90 | 1.78 | 2.682 (6) | 175 |
N2—H2A···S1ii | 0.90 | 2.44 | 3.336 (6) | 173 |
Symmetry codes: (i) −x, −y+1, −z; (ii) −x, −y+2, −z. |