Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807032722/lh2445sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807032722/lh2445Isup2.hkl |
CCDC reference: 657544
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.005 Å
- R factor = 0.045
- wR factor = 0.122
- Data-to-parameter ratio = 15.6
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for S1 - C1 .. 6.57 su PLAT230_ALERT_2_C Hirshfeld Test Diff for O4 - N3 .. 6.01 su PLAT230_ALERT_2_C Hirshfeld Test Diff for N3 - C15 .. 6.26 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C12 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C14 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C16
Alert level G PLAT794_ALERT_5_G Check Predicted Bond Valency for Co1 (2) 1.96 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 3
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 7 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
For related crystal structures, see: Desiderato et al. (1971), Shi et al. (2006).
15 ml H2O solution containing Co(ClO4)2.6H2O (0.1578 g, 0.431 mmol) and NaSCN (0.0702 g, 0.866 mmol) was added into 20 ml 8-hydroxyquinoline N-oxide (0.1321 g, 0.820 mmol) ethanol solution, and stirred for a few minutes. The red single crystals were obtained after the mixed solution had been allowed to stand at room temperature for four weeks. The strong and sharp IR peaks at 1399 cm-1 may be attributed to the stretching vibrations of the C=C and C=N bonds, whereas peak at 2088 cm-1 is assigned to the stretching vibration of thiocyanate group.
H atoms of water molecule were located in a difference Fourier map and refined as riding in their as-found positions, with O—H = 0.841–0.846 Å, Uiso(H) = 1.5 Ueq(O). Other H atoms were placed in calculated positions, and refined as riding, with C—H = 0.93 Å, Uiso(H) = 1.2eq(C); O—H = 0.82 Å, Uiso(H) = 1.5 Ueq(O) for hydroxyl groups.
The thiocyanate anion is a versatile ligand and a large number of complexes have been synthisized with it as a termianl or as a bridging ligand (e.g. Shi et al., 2006). Our interest in complexes containing the thiocyanate ligand resulted in us obtaining the title adduct. Here we report its cystal structure. The crystal structure of 8-hydroxyquinoline N-oxide has previously been reported (Desiderato et al., 1971).
Figure 1 shows a symmetry complete complex molecule and a symmetry unique 8-hydroxyquinoline molecule. Atom Co1 is in a slightly distorted octahedral CoN2O4 coordination geometry. In the crystal structure both the uncoordinated and coordinated 8-hydroxyquinoline molecules contain intramolecular O—H···O and O—H···N hydrogen bonds. Intermolecular O—H···O and C—H···S hydrogen bonds are observed between uncoordinated 8-hydroxyquinoline molecules and complex molecules (Fig. 2). In addition, there is a weak π-π stacking interaction between adjacent C11—C16 and N2/C6—C10 rings, with Cg1···Cg2 = 3.7554 (18) Å and Cg1···Cg2perp = 3.471 Å [Cg1···Cg2 is the distance between the two ring centroids, and Cg1···Cg2perp is the perpendicular distance of the two rings]. The dihedral anagle of the planes of the two rings is 14.6°. The overall result of the hydrogen bonding and π···π stacking interactions leads to the formation of a super-molecular three-dimensional structure.
For related crystal structures, see: Desiderato et al. (1971), Shi et al. (2006).
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
[Co(NCS)2(C9H7NO2)2(H2O)2].2C9H7NO2 | F(000) = 882 |
Mr = 855.75 | Dx = 1.518 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 3119 reflections |
a = 8.6381 (13) Å | θ = 2.4–24.1° |
b = 17.133 (3) Å | µ = 0.64 mm−1 |
c = 12.6809 (19) Å | T = 298 K |
β = 93.967 (2)° | Block, red |
V = 1872.2 (5) Å3 | 0.46 × 0.38 × 0.21 mm |
Z = 2 |
Bruker SMART APEX CCD diffractometer | 4049 independent reflections |
Radiation source: fine-focus sealed tube | 2959 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
φ and ω scans | θmax = 27.0°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→11 |
Tmin = 0.758, Tmax = 0.878 | k = −20→21 |
10783 measured reflections | l = −11→16 |
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 = 0.99 | w = 1/[σ2(Fo2) + (0.0713P)2 + 0.0781P] where P = (Fo2 + 2Fc2)/3 |
4049 reflections | (Δ/σ)max = 0.002 |
259 parameters | Δρmax = 0.33 e Å−3 |
3 restraints | Δρmin = −0.22 e Å−3 |
[Co(NCS)2(C9H7NO2)2(H2O)2].2C9H7NO2 | V = 1872.2 (5) Å3 |
Mr = 855.75 | Z = 2 |
Monoclinic, P21/n | Mo Kα radiation |
a = 8.6381 (13) Å | µ = 0.64 mm−1 |
b = 17.133 (3) Å | T = 298 K |
c = 12.6809 (19) Å | 0.46 × 0.38 × 0.21 mm |
β = 93.967 (2)° |
Bruker SMART APEX CCD diffractometer | 4049 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2959 reflections with I > 2σ(I) |
Tmin = 0.758, Tmax = 0.878 | Rint = 0.026 |
10783 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 3 restraints |
wR(F2) = 0.122 | H-atom parameters constrained |
S = 0.99 | Δρmax = 0.33 e Å−3 |
4049 reflections | Δρmin = −0.22 e Å−3 |
259 parameters |
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 | ||
O1 | 0.30709 (16) | 0.07591 (9) | 0.46163 (12) | 0.0570 (4) | |
H6 | 0.2606 | 0.0565 | 0.4069 | 0.085* | |
H7 | 0.2497 | 0.0762 | 0.5126 | 0.085* | |
Co1 | 0.5000 | 0.0000 | 0.5000 | 0.04581 (15) | |
O2 | 0.63297 (17) | 0.09338 (8) | 0.56295 (12) | 0.0520 (4) | |
N2 | 0.69243 (19) | 0.15070 (10) | 0.50537 (13) | 0.0479 (4) | |
O5 | 1.0743 (2) | 0.07773 (12) | 0.61024 (16) | 0.0881 (6) | |
H2 | 1.0359 | 0.0360 | 0.6264 | 0.132* | |
C7 | 0.6420 (2) | 0.22599 (13) | 0.51917 (16) | 0.0497 (5) | |
C15 | 0.9009 (2) | 0.11953 (14) | 0.73717 (18) | 0.0545 (5) | |
O3 | 0.4624 (2) | 0.19045 (10) | 0.65009 (14) | 0.0710 (5) | |
H1 | 0.4987 | 0.1473 | 0.6384 | 0.107* | |
N1 | 0.5638 (2) | 0.01197 (11) | 0.34865 (16) | 0.0576 (5) | |
N3 | 0.8489 (2) | 0.04347 (14) | 0.75126 (17) | 0.0678 (6) | |
C8 | 0.8003 (3) | 0.13268 (18) | 0.4404 (2) | 0.0678 (7) | |
H8 | 0.8319 | 0.0811 | 0.4343 | 0.081* | |
C1 | 0.6113 (3) | 0.02121 (12) | 0.26736 (18) | 0.0494 (5) | |
C16 | 0.8379 (3) | 0.18037 (19) | 0.7958 (2) | 0.0733 (8) | |
C9 | 0.8669 (3) | 0.1907 (3) | 0.3808 (2) | 0.0929 (11) | |
H9 | 0.9425 | 0.1781 | 0.3348 | 0.111* | |
C6 | 0.7082 (3) | 0.28558 (17) | 0.4597 (2) | 0.0728 (8) | |
C2 | 0.5277 (3) | 0.24412 (14) | 0.59013 (18) | 0.0566 (6) | |
C14 | 1.0138 (3) | 0.13580 (16) | 0.66616 (19) | 0.0606 (6) | |
C4 | 0.5457 (5) | 0.37788 (19) | 0.5420 (3) | 0.1031 (12) | |
H4 | 0.5125 | 0.4290 | 0.5506 | 0.124* | |
O4 | 0.9025 (2) | −0.01479 (11) | 0.69366 (18) | 0.0851 (6) | |
C3 | 0.4817 (3) | 0.31982 (17) | 0.5988 (2) | 0.0793 (8) | |
H3 | 0.4053 | 0.3322 | 0.6443 | 0.095* | |
C13 | 1.0592 (3) | 0.2099 (2) | 0.6527 (3) | 0.0868 (9) | |
H13 | 1.1338 | 0.2209 | 0.6053 | 0.104* | |
C18 | 0.6822 (4) | 0.0881 (3) | 0.8789 (3) | 0.1141 (15) | |
H18 | 0.6098 | 0.0767 | 0.9276 | 0.137* | |
C19 | 0.7415 (3) | 0.0290 (2) | 0.8207 (3) | 0.0929 (10) | |
H19 | 0.7069 | −0.0219 | 0.8294 | 0.111* | |
C10 | 0.8200 (4) | 0.2656 (3) | 0.3908 (2) | 0.0954 (11) | |
H10 | 0.8634 | 0.3043 | 0.3508 | 0.114* | |
C12 | 0.9966 (5) | 0.2699 (2) | 0.7082 (4) | 0.1114 (13) | |
H12 | 1.0298 | 0.3208 | 0.6972 | 0.134* | |
C11 | 0.8899 (5) | 0.2572 (2) | 0.7773 (3) | 0.1041 (12) | |
H11 | 0.8494 | 0.2989 | 0.8134 | 0.125* | |
C5 | 0.6557 (5) | 0.36344 (18) | 0.4736 (3) | 0.0981 (11) | |
H5 | 0.6968 | 0.4041 | 0.4359 | 0.118* | |
C17 | 0.7273 (4) | 0.1617 (3) | 0.8661 (3) | 0.1088 (14) | |
H17 | 0.6840 | 0.2012 | 0.9049 | 0.131* | |
S1 | 0.67766 (10) | 0.03564 (5) | 0.15248 (6) | 0.0848 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0554 (9) | 0.0602 (9) | 0.0560 (9) | 0.0069 (7) | 0.0085 (7) | −0.0016 (7) |
Co1 | 0.0487 (2) | 0.0473 (2) | 0.0425 (2) | 0.00069 (17) | 0.01068 (17) | 0.00210 (17) |
O2 | 0.0607 (9) | 0.0485 (8) | 0.0474 (8) | −0.0054 (7) | 0.0081 (7) | 0.0023 (7) |
N2 | 0.0430 (9) | 0.0597 (11) | 0.0413 (9) | −0.0064 (8) | 0.0058 (7) | −0.0031 (8) |
O5 | 0.0686 (11) | 0.1132 (15) | 0.0857 (14) | 0.0141 (11) | 0.0285 (10) | −0.0130 (12) |
C7 | 0.0521 (12) | 0.0533 (12) | 0.0427 (11) | −0.0106 (10) | −0.0037 (9) | 0.0011 (10) |
C15 | 0.0407 (11) | 0.0715 (15) | 0.0501 (13) | 0.0027 (10) | −0.0042 (9) | −0.0024 (11) |
O3 | 0.0749 (11) | 0.0797 (12) | 0.0614 (11) | 0.0046 (9) | 0.0259 (9) | −0.0049 (9) |
N1 | 0.0611 (12) | 0.0670 (12) | 0.0460 (10) | −0.0026 (9) | 0.0128 (9) | 0.0020 (9) |
N3 | 0.0524 (11) | 0.0882 (16) | 0.0613 (13) | 0.0012 (11) | −0.0069 (10) | 0.0103 (12) |
C8 | 0.0476 (13) | 0.0967 (19) | 0.0603 (15) | −0.0067 (12) | 0.0124 (11) | −0.0184 (14) |
C1 | 0.0536 (12) | 0.0451 (11) | 0.0505 (13) | 0.0002 (9) | 0.0097 (10) | −0.0021 (9) |
C16 | 0.0552 (14) | 0.102 (2) | 0.0603 (16) | 0.0173 (14) | −0.0110 (12) | −0.0229 (15) |
C9 | 0.0602 (17) | 0.162 (3) | 0.0589 (18) | −0.041 (2) | 0.0204 (14) | −0.014 (2) |
C6 | 0.0731 (17) | 0.0812 (18) | 0.0616 (16) | −0.0341 (14) | −0.0132 (14) | 0.0175 (14) |
C2 | 0.0580 (13) | 0.0606 (14) | 0.0500 (13) | 0.0034 (11) | −0.0061 (11) | −0.0113 (11) |
C14 | 0.0453 (12) | 0.0802 (17) | 0.0562 (14) | 0.0019 (12) | 0.0026 (10) | 0.0001 (12) |
C4 | 0.122 (3) | 0.0600 (18) | 0.121 (3) | 0.002 (2) | −0.039 (3) | −0.007 (2) |
O4 | 0.0760 (13) | 0.0685 (12) | 0.1083 (17) | 0.0125 (9) | −0.0125 (12) | −0.0076 (11) |
C3 | 0.0859 (19) | 0.0710 (18) | 0.078 (2) | 0.0145 (15) | −0.0143 (16) | −0.0179 (15) |
C13 | 0.0696 (18) | 0.105 (2) | 0.085 (2) | −0.0220 (17) | −0.0049 (16) | 0.0168 (19) |
C18 | 0.063 (2) | 0.229 (5) | 0.0507 (18) | 0.002 (3) | 0.0101 (15) | 0.012 (3) |
C19 | 0.0594 (16) | 0.140 (3) | 0.077 (2) | −0.0225 (18) | −0.0114 (16) | 0.042 (2) |
C10 | 0.083 (2) | 0.138 (3) | 0.0649 (19) | −0.063 (2) | 0.0007 (16) | 0.023 (2) |
C12 | 0.107 (3) | 0.078 (2) | 0.142 (4) | −0.015 (2) | −0.043 (3) | −0.005 (2) |
C11 | 0.097 (2) | 0.091 (3) | 0.118 (3) | 0.024 (2) | −0.038 (2) | −0.044 (2) |
C5 | 0.120 (3) | 0.0609 (18) | 0.107 (3) | −0.0371 (19) | −0.035 (2) | 0.0288 (17) |
C17 | 0.0613 (19) | 0.203 (4) | 0.062 (2) | 0.029 (2) | 0.0004 (15) | −0.039 (3) |
S1 | 0.1174 (6) | 0.0820 (5) | 0.0604 (4) | −0.0090 (4) | 0.0450 (4) | −0.0001 (4) |
O1—Co1 | 2.1431 (14) | C1—S1 | 1.621 (2) |
O1—H6 | 0.8463 | C16—C17 | 1.389 (5) |
O1—H7 | 0.8407 | C16—C11 | 1.416 (5) |
Co1—N1i | 2.044 (2) | C9—C10 | 1.354 (5) |
Co1—N1 | 2.044 (2) | C9—H9 | 0.9300 |
Co1—O2 | 2.0951 (14) | C6—C10 | 1.390 (4) |
Co1—O2i | 2.0951 (14) | C6—C5 | 1.424 (4) |
Co1—O1i | 2.1431 (14) | C2—C3 | 1.363 (3) |
O2—N2 | 1.346 (2) | C14—C13 | 1.344 (4) |
N2—C8 | 1.322 (3) | C4—C5 | 1.353 (5) |
N2—C7 | 1.376 (3) | C4—C3 | 1.367 (4) |
O5—C14 | 1.348 (3) | C4—H4 | 0.9300 |
O5—H2 | 0.8200 | C3—H3 | 0.9300 |
C7—C6 | 1.413 (3) | C13—C12 | 1.377 (5) |
C7—C2 | 1.416 (3) | C13—H13 | 0.9300 |
C15—N3 | 1.394 (3) | C18—C17 | 1.333 (5) |
C15—C14 | 1.401 (3) | C18—C19 | 1.373 (5) |
C15—C16 | 1.411 (3) | C18—H18 | 0.9300 |
O3—C2 | 1.342 (3) | C19—H19 | 0.9300 |
O3—H1 | 0.8200 | C10—H10 | 0.9300 |
N1—C1 | 1.146 (3) | C12—C11 | 1.333 (5) |
N3—O4 | 1.338 (3) | C12—H12 | 0.9300 |
N3—C19 | 1.345 (4) | C11—H11 | 0.9300 |
C8—C9 | 1.397 (4) | C5—H5 | 0.9300 |
C8—H8 | 0.9300 | C17—H17 | 0.9300 |
Co1—O1—H6 | 105.4 | C10—C9—H9 | 120.5 |
Co1—O1—H7 | 108.6 | C8—C9—H9 | 120.5 |
H6—O1—H7 | 111.2 | C10—C6—C7 | 118.8 (3) |
N1i—Co1—N1 | 180.0 | C10—C6—C5 | 123.4 (3) |
N1i—Co1—O2 | 83.99 (7) | C7—C6—C5 | 117.8 (3) |
N1—Co1—O2 | 96.01 (7) | O3—C2—C3 | 118.0 (2) |
N1i—Co1—O2i | 96.01 (7) | O3—C2—C7 | 123.3 (2) |
N1—Co1—O2i | 83.99 (7) | C3—C2—C7 | 118.7 (2) |
O2—Co1—O2i | 180.00 (5) | C13—C14—O5 | 120.3 (3) |
N1i—Co1—O1 | 91.03 (7) | C13—C14—C15 | 119.5 (3) |
N1—Co1—O1 | 88.97 (7) | O5—C14—C15 | 120.3 (2) |
O2—Co1—O1 | 91.16 (6) | C5—C4—C3 | 122.2 (3) |
O2i—Co1—O1 | 88.84 (6) | C5—C4—H4 | 118.9 |
N1i—Co1—O1i | 88.97 (7) | C3—C4—H4 | 118.9 |
N1—Co1—O1i | 91.03 (7) | C2—C3—C4 | 121.2 (3) |
O2—Co1—O1i | 88.84 (6) | C2—C3—H3 | 119.4 |
O2i—Co1—O1i | 91.16 (6) | C4—C3—H3 | 119.4 |
O1—Co1—O1i | 180.00 (8) | C14—C13—C12 | 120.8 (3) |
N2—O2—Co1 | 124.75 (12) | C14—C13—H13 | 119.6 |
C8—N2—O2 | 118.6 (2) | C12—C13—H13 | 119.6 |
C8—N2—C7 | 122.7 (2) | C17—C18—C19 | 120.7 (3) |
O2—N2—C7 | 118.60 (16) | C17—C18—H18 | 119.7 |
C14—O5—H2 | 109.5 | C19—C18—H18 | 119.7 |
N2—C7—C6 | 117.8 (2) | N3—C19—C18 | 121.0 (3) |
N2—C7—C2 | 121.80 (19) | N3—C19—H19 | 119.5 |
C6—C7—C2 | 120.4 (2) | C18—C19—H19 | 119.5 |
N3—C15—C14 | 120.9 (2) | C9—C10—C6 | 121.2 (3) |
N3—C15—C16 | 118.9 (2) | C9—C10—H10 | 119.4 |
C14—C15—C16 | 120.2 (2) | C6—C10—H10 | 119.4 |
C2—O3—H1 | 109.5 | C11—C12—C13 | 121.8 (4) |
C1—N1—Co1 | 174.2 (2) | C11—C12—H12 | 119.1 |
O4—N3—C19 | 120.0 (3) | C13—C12—H12 | 119.1 |
O4—N3—C15 | 120.0 (2) | C12—C11—C16 | 120.2 (3) |
C19—N3—C15 | 120.0 (3) | C12—C11—H11 | 119.9 |
N2—C8—C9 | 120.4 (3) | C16—C11—H11 | 119.9 |
N2—C8—H8 | 119.8 | C4—C5—C6 | 119.6 (3) |
C9—C8—H8 | 119.8 | C4—C5—H5 | 120.2 |
N1—C1—S1 | 179.1 (2) | C6—C5—H5 | 120.2 |
C17—C16—C15 | 118.4 (3) | C18—C17—C16 | 121.0 (4) |
C17—C16—C11 | 124.1 (3) | C18—C17—H17 | 119.5 |
C15—C16—C11 | 117.5 (3) | C16—C17—H17 | 119.5 |
C10—C9—C8 | 119.1 (3) | ||
N1i—Co1—O2—N2 | −162.65 (15) | N2—C7—C2—C3 | −179.1 (2) |
N1—Co1—O2—N2 | 17.35 (15) | C6—C7—C2—C3 | 0.8 (3) |
O1—Co1—O2—N2 | −71.73 (14) | N3—C15—C14—C13 | 178.6 (2) |
O1i—Co1—O2—N2 | 108.27 (14) | C16—C15—C14—C13 | −1.4 (4) |
Co1—O2—N2—C8 | −65.6 (2) | N3—C15—C14—O5 | −0.1 (3) |
Co1—O2—N2—C7 | 116.45 (17) | C16—C15—C14—O5 | 179.9 (2) |
C8—N2—C7—C6 | 0.8 (3) | O3—C2—C3—C4 | 178.5 (3) |
O2—N2—C7—C6 | 178.66 (18) | C7—C2—C3—C4 | −1.2 (4) |
C8—N2—C7—C2 | −179.2 (2) | C5—C4—C3—C2 | 0.9 (5) |
O2—N2—C7—C2 | −1.4 (3) | O5—C14—C13—C12 | 179.0 (3) |
C14—C15—N3—O4 | −2.6 (3) | C15—C14—C13—C12 | 0.3 (4) |
C16—C15—N3—O4 | 177.5 (2) | O4—N3—C19—C18 | −178.5 (3) |
C14—C15—N3—C19 | 179.3 (2) | C15—N3—C19—C18 | −0.4 (4) |
C16—C15—N3—C19 | −0.7 (3) | C17—C18—C19—N3 | 1.5 (5) |
O2—N2—C8—C9 | −178.8 (2) | C8—C9—C10—C6 | 0.6 (5) |
C7—N2—C8—C9 | −1.0 (4) | C7—C6—C10—C9 | −0.7 (4) |
N3—C15—C16—C17 | 0.6 (4) | C5—C6—C10—C9 | 179.6 (3) |
C14—C15—C16—C17 | −179.4 (2) | C14—C13—C12—C11 | 0.3 (5) |
N3—C15—C16—C11 | −178.2 (2) | C13—C12—C11—C16 | 0.2 (5) |
C14—C15—C16—C11 | 1.9 (4) | C17—C16—C11—C12 | −180.0 (3) |
N2—C8—C9—C10 | 0.2 (4) | C15—C16—C11—C12 | −1.3 (4) |
N2—C7—C6—C10 | 0.0 (3) | C3—C4—C5—C6 | −0.2 (5) |
C2—C7—C6—C10 | −179.9 (2) | C10—C6—C5—C4 | 179.6 (3) |
N2—C7—C6—C5 | 179.8 (2) | C7—C6—C5—C4 | −0.1 (4) |
C2—C7—C6—C5 | −0.2 (4) | C19—C18—C17—C16 | −1.6 (6) |
N2—C7—C2—O3 | 1.2 (3) | C15—C16—C17—C18 | 0.6 (5) |
C6—C7—C2—O3 | −178.8 (2) | C11—C16—C17—C18 | 179.2 (3) |
Symmetry code: (i) −x+1, −y, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H7···O5ii | 0.84 | 2.02 | 2.849 (2) | 168 |
O1—H6···O4i | 0.85 | 1.97 | 2.786 (3) | 162 |
C5—H5···S1iii | 0.93 | 2.77 | 3.695 (4) | 173 |
C12—H12···S1iv | 0.93 | 2.85 | 3.768 (4) | 170 |
O3—H1···O2 | 0.82 | 1.81 | 2.527 (2) | 145 |
O3—H1···N2 | 0.82 | 2.46 | 2.878 (2) | 113 |
O5—H2···O4 | 0.82 | 1.72 | 2.460 (3) | 150 |
O5—H2···N3 | 0.82 | 2.34 | 2.796 (3) | 116 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) x−1, y, z; (iii) −x+3/2, y+1/2, −z+1/2; (iv) x+1/2, −y+1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [Co(NCS)2(C9H7NO2)2(H2O)2].2C9H7NO2 |
Mr | 855.75 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 298 |
a, b, c (Å) | 8.6381 (13), 17.133 (3), 12.6809 (19) |
β (°) | 93.967 (2) |
V (Å3) | 1872.2 (5) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.64 |
Crystal size (mm) | 0.46 × 0.38 × 0.21 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.758, 0.878 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10783, 4049, 2959 |
Rint | 0.026 |
(sin θ/λ)max (Å−1) | 0.639 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.122, 0.99 |
No. of reflections | 4049 |
No. of parameters | 259 |
No. of restraints | 3 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.33, −0.22 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SAINT, SHELXTL (Bruker, 2001), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H7···O5i | 0.84 | 2.02 | 2.849 (2) | 168 |
O1—H6···O4ii | 0.85 | 1.97 | 2.786 (3) | 162 |
C5—H5···S1iii | 0.93 | 2.77 | 3.695 (4) | 173 |
C12—H12···S1iv | 0.93 | 2.85 | 3.768 (4) | 170 |
O3—H1···O2 | 0.82 | 1.81 | 2.527 (2) | 145 |
O3—H1···N2 | 0.82 | 2.46 | 2.878 (2) | 113 |
O5—H2···O4 | 0.82 | 1.72 | 2.460 (3) | 150 |
O5—H2···N3 | 0.82 | 2.34 | 2.796 (3) | 116 |
Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y, −z+1; (iii) −x+3/2, y+1/2, −z+1/2; (iv) x+1/2, −y+1/2, z+1/2. |
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The thiocyanate anion is a versatile ligand and a large number of complexes have been synthisized with it as a termianl or as a bridging ligand (e.g. Shi et al., 2006). Our interest in complexes containing the thiocyanate ligand resulted in us obtaining the title adduct. Here we report its cystal structure. The crystal structure of 8-hydroxyquinoline N-oxide has previously been reported (Desiderato et al., 1971).
Figure 1 shows a symmetry complete complex molecule and a symmetry unique 8-hydroxyquinoline molecule. Atom Co1 is in a slightly distorted octahedral CoN2O4 coordination geometry. In the crystal structure both the uncoordinated and coordinated 8-hydroxyquinoline molecules contain intramolecular O—H···O and O—H···N hydrogen bonds. Intermolecular O—H···O and C—H···S hydrogen bonds are observed between uncoordinated 8-hydroxyquinoline molecules and complex molecules (Fig. 2). In addition, there is a weak π-π stacking interaction between adjacent C11—C16 and N2/C6—C10 rings, with Cg1···Cg2 = 3.7554 (18) Å and Cg1···Cg2perp = 3.471 Å [Cg1···Cg2 is the distance between the two ring centroids, and Cg1···Cg2perp is the perpendicular distance of the two rings]. The dihedral anagle of the planes of the two rings is 14.6°. The overall result of the hydrogen bonding and π···π stacking interactions leads to the formation of a super-molecular three-dimensional structure.