research communications
κ2N1,S)nickel(II)
of bis(acetophenone 4-benzoylthiosemicarbazonato-aDepartment of Chemistry, Faculty of Science, Universiti Teknologi Malaysia, 81310 UTM Johor Bahru, Johor, Malaysia, bDepartment of Chemistry, School of Science, Faculty of Science & Education, University of Sulaimani, Kurdistan Region, Iraq, cCentre for Sustainable Nanomaterials, Universiti Teknologi Malaysia, 81310 UTM Johor Bahru, Johor, Malaysia, and dX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800, USM, Penang, Malaysia
*Correspondence e-mail: mustaqim@usm.my
In the 16H14N3OS)2], the nickel ion is tetracoordinated in a distorted square-planar geometry by two independent molecules of the ligand which act as mononegative bidentate N,S-donors and form two five-membered chelate rings. The ligands are in trans (E) conformations with respect to the C=N bonds. The close approach of hydrogen atoms to the Ni2+ atom suggests anagostic interactions (Ni⋯H—C) are present. The is built up by a network of two C—H⋯O interactions. One of the interactions forms inversion dimers and the other links the molecules into infinite chains parallel to [100]. In addition, a weak C—H⋯π interaction is also present.
of the title complex, [Ni(CKeywords: crystal structure; thiosemicarbazone; nickel(II); anagostic interactions; C—H⋯O interactions.
CCDC reference: 1476076
1. Chemical context
Thiosemicarbazones containing N and S donor atoms have been widely used in metal coordination chemistry due to their structural flexibility and versatility (Pelosi et al., 2010; Yousef et al., 2013; Jagadeesh et al., 2015). The chemistry of transition metal complexes of thiosemicarbazones has gained significant attention due to their potential medicinal applications (Pelosi et al., 2010; Li et al., 2012; Manikandan et al., 2014). The variable mode of binding of thiosemicarbazone towards nickel has encouraged us to explore its coordination chemistry further since nickel has the ability to take up different coordination environments. Nickel complexes are known to catalyse carbon–carbon cross-coupling and other reactions (Suganthy et al., 2013; Wang et al., 2014).
2. Structural commentary
The molecular structure of the title complex (I) with the numbering scheme is shown in Fig. 1. The nickel ion is tetra-coordinated in a square-planar geometry by two crystallographically independent molecules of the ligand which act as mononegative bidentate N,S-donors and form two five-membered chelate rings. The ligands are in trans (E) conformations with respect to the C7=N1 and C23=N4 bonds, as evidenced by the torsion angles N2—N1—C7—C6 = −171.0 (2) and N5—N4—C23—C22 = −171.8 (2)°, respectively. This is in close agreement with previously reported data (Sampath et al., 2013, Suganthy et al., 2013). A remarkable tetrahedrally distorted square-planar coordination geometry is shown by the nickel metal ion, with the two ligands displaying a less common cis N,S-chelation mode (de Oliveira et al., 2014). The Ni—S and Ni—N bond lengths (Table 1) and the N1—Ni1—S2 and N4—Ni1-S1 bond angle of 159.86 (7) and 159.67 (7)°, respectively, confirm the distortion from a typical coordination geometry.
|
Upon II ion, the ligands underwent deprotonation from the tautomeric thiolates and their negative charges are delocalized over atoms N1–N2–C9–S1 and N4–N5–C22–S2. Consequently, the bond lengths S1—C9 in one ligand and S2—C25 in the other ligand are 1.728 (3) and 1.735 (3) Å, respectively, which are consistent with single-bond character (Sankaraperumal et al., 2013). Furthermore, the Ni—N [1.922 (2) and 1.928 (2) Å] and Ni—S bond lengths [range 2.1489 (10) and 2.1518 (10) Å] are consistent with those in similar reported compounds. The S—C [1.728 and 1.735 (3)Å] and N—C [1.293 (3) and 1.294 (3) Å] bond lengths of the ligand are consistent with literature values (Sankaraperumal et al., 2013, de Oliveira et al., 2014).
to the NiNotably, two anagostic interactions in the trans-arrangement are observed in the title complex between the nickel(II) ion and the aromatic C—H groups (Fig. 2). The Ni1⋯H1A and Ni1⋯H17A distances are 2.616 and 2.527 Å, respectively, which are shorter than the van der Waals radii sum for Ni (1.63 Å; Bondi, 1964) and H (1.10 Å; Rowland & Taylor, 1996). In addition, the Ni1—H1A—C1 and Ni1—H17A—C17 bond angles are 109.6 and 112.7°, respectively. These observed values of contact distances and bond angles fall in the range for anagostic interactions reported by Brookhart et al. (2007). Similar observations have been reported recently by de Oliveira et al. (2014).
3. Supramolecular features
The contains a network of C—H⋯O interactions (Table 2). First the interaction C16—H16A⋯O1 links pairs of molecules to form inversion dimers enclosing centrosymmetric R22(10) ring motifs, as shown in Fig. 3. These dimers are further linked by C21—H21A⋯O2 interactions, resulting an infinite chains along [100] (Fig. 4). In addition, a C—H⋯π interaction is also present (Table 2).
of (I)4. Synthesis and crystallization
The title complex was prepared by adding a solution of acetophenone-4-benzoyl-3-thiosemicarbazone (75 mg; 0.25 mmol) in dichloromethane (10 mL) dropwise to a stirred solution of nickel(II) nitrate hexahydrate (47.5 mg; 0.26 mmol) in 2-propanol (10 mL) in a small beaker. The resulting mixture solution was stirred continuously for 1 h at 318–323 K. The resultant green precipitate was separated by vacuum filtration, washed with 2-propanol and then with ether, and dried in a vacuum desiccator over dry silica gel. Single crystals suitable for X-ray analysis were obtained after slow evaporation of a dichloromethane solution saturated with 2-propanol. Yield; 52.5 mg, 65%. Melting point: 521–523 K.
5. Refinement
Crystal data, data collection and structure . The H atoms attached to nitrogen were located in difference Fourier maps and freely refined. The remaining H atoms were positioned geometrically and refined using a riding model with C—H = 0.95–0.98 Å and Uiso(H) = 1.2Ueq(C) or 1.5Ueq(C-methyl). A rotating group model was applied to the methyl groups.
details are summarized in Table 3Supporting information
CCDC reference: 1476076
10.1107/S2056989016006873/pj2029sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2056989016006873/pj2029Isup2.hkl
Thiosemicarbazones containing N and S donor atoms have been widely used in metal coordination chemistry due to their structural flexibility and versatility (Pelosi et al. 2010; Yousef et al. 2013; Jagadeesh et al. 2015). The chemistry of transition metal complexes of thiosemicarbazones has gained significant attention due to their potential medicinal applications (Pelosi et al. 2010; Li et al. 2012; Manikandan et al. 2014). The variable mode of binding of thiosemicarbazone towards nickel has encouraged us to explore its coordination chemistry further since nickel has the ability to take up different coordination environments. Nickel complexes are known to catalyse carbon–carbon cross-coupling and other reactions (Suganthy et al. 2013; Wang et al. 2014).
The molecular structure of the title complex (I) with the numbering scheme is shown in Fig. 1. The nickel ion is tetra-coordinated in a square-planar geometry by two crystallographically independent molecules of the ligand which act as mononegative bidentate N,S-donors and form two five-membered chelate rings. The ligands are in trans (E) conformations with respect to the C7═N1 and C23═N4 bonds, as evidenced by the torsion angles N2—N1—C7—C6 = -171.0 (2) and N5—N4—C23—C22 = -171.8 (2)°, respectively. This is in close agreement with previously reported data (Sampath et al., 2013, Suganthy et al., 2013). A remarkable tetrahedrally distorted square-planar coordination geometry is shown by the nickel metal ion, with the two ligands displaying a less common cis N,S-chelation mode (de Oliveira et al., 2014). The Ni—S and Ni—N bond lengths (Table 1) and the N1—Ni1—S2 and N4—Ni1—S1 bond angle of 159.86 (7) and 159.67 (7)°, respectively, confirm the distortion from a typical coordination geometry.
Upon
to the NiII ion, the ligands underwent deprotonation from the tautomeric thiolates and their negative charges were delocalized over atoms N1–N2–C9–S1 and N4–N5–C22–S2. Consequently, the bond lengths S1—C9 in one ligand and S2—C25 in the other ligand are 1.728 (3) and 1.735 (3) Å, respectively, which are consistent with single-bond character (Sankaraperumal et al., 2013). Furthermore, the Ni—N [1.922 (2) and 1.928 (2) Å] and Ni—S bond lengths [range 2.1489 (10) and 2.1518 (10) Å] are consistent with those in similar reported compounds. The S—C [1.728 and 1.735 (3)Å] and N—C [1.293 (3) and 1.294 (3) Å] bond lengths of the ligand are consistent with literature values (Sankaraperumal et al., 2013, de Oliveira et al., 2014).Notably, two anagostic interactions in the trans-arrangement are observed in the title complex between the nickel(II) ion and the aromatic C—H groups (Fig. 2). The Ni1···H1A and Ni1···H17A distances are 2.616 and 2.527 Å, respectively, which are shorter than the van der Waals radii sum for Ni (1.63 Å; Bondi 1964) and H (1.10 Å; Rowland & Taylor, 1996). In addition, the Ni1—H1A—C1 and Ni1—H17A—C17 bond angles are 109.6 and 112.7°, respectively. These observed values of contact distances and bond angles fall in the range for anagostic interactions reported by Brookhart et al. (2007). Similar observations have been reported recently by de Oliveira et al. (2014).
The π interaction is also present (Table 2).
of (I) contains a network of C—H···O interactions (Table 2). First the interaction C16—H16A···O1 links pairs of molecules to form inversion dimers enclosing centrosymmetric R22(10) ring motifs, as shown in Fig. 3. These dimers are further linked by C21—H21A···O2 interactions, resulting an infinite chains along [100] (Fig. 4). In addition, a C—H···The title complex was prepared by adding a solution of acetophenone-4-benzoyl-3-thiosemicarbazone (75 mg; 0.25 mmol) in dichloromethane (10 mL) dropwise to a stirred solution of nickel(II) nitrate hexahydrate (47.5 mg; 0.26 mmol) in 2-propanol (10 mL) in a small beaker. The resulting mixture solution was stirred continuously for 1 h at 318–323 K. The resultant green precipitate was separated by vacuum filtration, washed with 2-propanol and then with ether, and dried in a vacuum desiccator over dry silica gel. Single crystals suitable for X-ray analysis were obtained after slow evaporation of a dichloromethane solution saturated with 2-propanol. Yield; 52.5 mg, 65%. Melting point: 521–523 K.
Crystal data, data collection and structure
details are summarized in Table 3. The H atoms attached to nitrogen were located in difference Fourier maps and freely refined. The remaining H atoms were positioned geometrically and refined using a riding model with C—H = 0.95–0.98 Å and Uiso(H) = 1.2Ueq(C) or 1.5Ueq(C-methyl). A rotating group model was applied to the methyl groups.Thiosemicarbazones containing N and S donor atoms have been widely used in metal coordination chemistry due to their structural flexibility and versatility (Pelosi et al. 2010; Yousef et al. 2013; Jagadeesh et al. 2015). The chemistry of transition metal complexes of thiosemicarbazones has gained significant attention due to their potential medicinal applications (Pelosi et al. 2010; Li et al. 2012; Manikandan et al. 2014). The variable mode of binding of thiosemicarbazone towards nickel has encouraged us to explore its coordination chemistry further since nickel has the ability to take up different coordination environments. Nickel complexes are known to catalyse carbon–carbon cross-coupling and other reactions (Suganthy et al. 2013; Wang et al. 2014).
The molecular structure of the title complex (I) with the numbering scheme is shown in Fig. 1. The nickel ion is tetra-coordinated in a square-planar geometry by two crystallographically independent molecules of the ligand which act as mononegative bidentate N,S-donors and form two five-membered chelate rings. The ligands are in trans (E) conformations with respect to the C7═N1 and C23═N4 bonds, as evidenced by the torsion angles N2—N1—C7—C6 = -171.0 (2) and N5—N4—C23—C22 = -171.8 (2)°, respectively. This is in close agreement with previously reported data (Sampath et al., 2013, Suganthy et al., 2013). A remarkable tetrahedrally distorted square-planar coordination geometry is shown by the nickel metal ion, with the two ligands displaying a less common cis N,S-chelation mode (de Oliveira et al., 2014). The Ni—S and Ni—N bond lengths (Table 1) and the N1—Ni1—S2 and N4—Ni1—S1 bond angle of 159.86 (7) and 159.67 (7)°, respectively, confirm the distortion from a typical coordination geometry.
Upon
to the NiII ion, the ligands underwent deprotonation from the tautomeric thiolates and their negative charges were delocalized over atoms N1–N2–C9–S1 and N4–N5–C22–S2. Consequently, the bond lengths S1—C9 in one ligand and S2—C25 in the other ligand are 1.728 (3) and 1.735 (3) Å, respectively, which are consistent with single-bond character (Sankaraperumal et al., 2013). Furthermore, the Ni—N [1.922 (2) and 1.928 (2) Å] and Ni—S bond lengths [range 2.1489 (10) and 2.1518 (10) Å] are consistent with those in similar reported compounds. The S—C [1.728 and 1.735 (3)Å] and N—C [1.293 (3) and 1.294 (3) Å] bond lengths of the ligand are consistent with literature values (Sankaraperumal et al., 2013, de Oliveira et al., 2014).Notably, two anagostic interactions in the trans-arrangement are observed in the title complex between the nickel(II) ion and the aromatic C—H groups (Fig. 2). The Ni1···H1A and Ni1···H17A distances are 2.616 and 2.527 Å, respectively, which are shorter than the van der Waals radii sum for Ni (1.63 Å; Bondi 1964) and H (1.10 Å; Rowland & Taylor, 1996). In addition, the Ni1—H1A—C1 and Ni1—H17A—C17 bond angles are 109.6 and 112.7°, respectively. These observed values of contact distances and bond angles fall in the range for anagostic interactions reported by Brookhart et al. (2007). Similar observations have been reported recently by de Oliveira et al. (2014).
The π interaction is also present (Table 2).
of (I) contains a network of C—H···O interactions (Table 2). First the interaction C16—H16A···O1 links pairs of molecules to form inversion dimers enclosing centrosymmetric R22(10) ring motifs, as shown in Fig. 3. These dimers are further linked by C21—H21A···O2 interactions, resulting an infinite chains along [100] (Fig. 4). In addition, a C—H···The title complex was prepared by adding a solution of acetophenone-4-benzoyl-3-thiosemicarbazone (75 mg; 0.25 mmol) in dichloromethane (10 mL) dropwise to a stirred solution of nickel(II) nitrate hexahydrate (47.5 mg; 0.26 mmol) in 2-propanol (10 mL) in a small beaker. The resulting mixture solution was stirred continuously for 1 h at 318–323 K. The resultant green precipitate was separated by vacuum filtration, washed with 2-propanol and then with ether, and dried in a vacuum desiccator over dry silica gel. Single crystals suitable for X-ray analysis were obtained after slow evaporation of a dichloromethane solution saturated with 2-propanol. Yield; 52.5 mg, 65%. Melting point: 521–523 K.
detailsCrystal data, data collection and structure
details are summarized in Table 3. The H atoms attached to nitrogen were located in difference Fourier maps and freely refined. The remaining H atoms were positioned geometrically and refined using a riding model with C—H = 0.95–0.98 Å and Uiso(H) = 1.2Ueq(C) or 1.5Ueq(C-methyl). A rotating group model was applied to the methyl groups.Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXL2014 (Sheldrick, 2015); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015), PLATON (Spek, 2009) and publCIF (Westrip, 2010).Fig. 1. The molecular structure of (I) showing 50% probability displacement ellipsoids. H atoms are shown as spheres of arbitrary radius. | |
Fig. 2. Two anagostic interactions (dashed lines) between the nickel(II) ion and the aromatic C—H groups. | |
Fig. 3. Inversion dimers found in complex (I), formed by C—H···O hydrogen bonds (dashed lines; see Table 2). | |
Fig. 4. A view along the c axis of the crystal packing of complex (I), showing the infinite chain [100] formed by C—H···O interaction (dashed lines; see Table 2). H atoms not involved in the hydrogen bonding have been omitted for clarity. |
[Ni(C16H14N3OS)2] | F(000) = 1352 |
Mr = 651.43 | Dx = 1.430 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 10.220 (3) Å | Cell parameters from 9846 reflections |
b = 15.468 (5) Å | θ = 2.2–30.1° |
c = 19.151 (6) Å | µ = 0.82 mm−1 |
β = 92.150 (5)° | T = 297 K |
V = 3025.1 (17) Å3 | Block, dark green |
Z = 4 | 0.19 × 0.18 × 0.09 mm |
Bruker APEX DUO CCD area-detector diffractometer | 4635 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.070 |
φ and ω scans | θmax = 26.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −12→12 |
k = −19→19 | |
43914 measured reflections | l = −23→23 |
5893 independent reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.048 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.100 | w = 1/[σ2(Fo2) + (0.0315P)2 + 3.0091P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
5893 reflections | Δρmax = 0.46 e Å−3 |
398 parameters | Δρmin = −0.38 e Å−3 |
[Ni(C16H14N3OS)2] | V = 3025.1 (17) Å3 |
Mr = 651.43 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 10.220 (3) Å | µ = 0.82 mm−1 |
b = 15.468 (5) Å | T = 297 K |
c = 19.151 (6) Å | 0.19 × 0.18 × 0.09 mm |
β = 92.150 (5)° |
Bruker APEX DUO CCD area-detector diffractometer | 5893 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 4635 reflections with I > 2σ(I) |
Rint = 0.070 | |
43914 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.100 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.46 e Å−3 |
5893 reflections | Δρmin = −0.38 e Å−3 |
398 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
Ni1 | 0.38656 (3) | 0.38363 (2) | 0.14831 (2) | 0.03092 (11) | |
S1 | 0.29568 (8) | 0.25816 (5) | 0.14900 (5) | 0.0468 (2) | |
S2 | 0.20856 (7) | 0.44818 (5) | 0.11538 (4) | 0.03977 (19) | |
O1 | 0.4015 (4) | 0.09249 (17) | 0.07102 (13) | 0.0989 (12) | |
O2 | 0.0116 (2) | 0.58787 (16) | 0.14021 (16) | 0.0740 (8) | |
N1 | 0.5206 (2) | 0.33342 (14) | 0.20917 (11) | 0.0313 (5) | |
N2 | 0.5355 (2) | 0.24301 (14) | 0.20848 (12) | 0.0359 (5) | |
N3 | 0.4341 (3) | 0.11462 (16) | 0.18572 (14) | 0.0417 (6) | |
N4 | 0.4758 (2) | 0.48357 (14) | 0.11409 (11) | 0.0323 (5) | |
N5 | 0.4058 (2) | 0.56192 (15) | 0.10985 (12) | 0.0363 (6) | |
N6 | 0.2077 (3) | 0.62374 (18) | 0.09826 (14) | 0.0437 (7) | |
C1 | 0.4607 (3) | 0.4993 (2) | 0.27376 (15) | 0.0421 (7) | |
H1A | 0.3864 | 0.4626 | 0.2691 | 0.051* | |
C2 | 0.4439 (4) | 0.5856 (2) | 0.28904 (18) | 0.0600 (10) | |
H2A | 0.3585 | 0.6081 | 0.2949 | 0.072* | |
C3 | 0.5504 (5) | 0.6388 (2) | 0.2958 (2) | 0.0709 (12) | |
H3A | 0.5388 | 0.6983 | 0.3061 | 0.085* | |
C4 | 0.6732 (5) | 0.6070 (2) | 0.2879 (2) | 0.0708 (12) | |
H4A | 0.7468 | 0.6444 | 0.2924 | 0.085* | |
C5 | 0.6910 (3) | 0.5205 (2) | 0.27322 (18) | 0.0532 (9) | |
H5A | 0.7770 | 0.4984 | 0.2687 | 0.064* | |
C6 | 0.5840 (3) | 0.46575 (18) | 0.26511 (14) | 0.0351 (6) | |
C7 | 0.6017 (3) | 0.37289 (18) | 0.25164 (14) | 0.0327 (6) | |
C8 | 0.7109 (3) | 0.3267 (2) | 0.28965 (17) | 0.0496 (8) | |
H8A | 0.7528 | 0.3657 | 0.3241 | 0.074* | |
H8B | 0.7755 | 0.3079 | 0.2563 | 0.074* | |
H8C | 0.6762 | 0.2761 | 0.3136 | 0.074* | |
C9 | 0.4336 (3) | 0.20575 (18) | 0.18243 (14) | 0.0362 (7) | |
C10 | 0.4225 (4) | 0.0628 (2) | 0.12850 (16) | 0.0483 (8) | |
C11 | 0.4392 (3) | −0.03163 (18) | 0.14117 (15) | 0.0383 (7) | |
C12 | 0.4104 (3) | −0.07032 (19) | 0.20340 (16) | 0.0422 (7) | |
H12A | 0.3823 | −0.0362 | 0.2412 | 0.051* | |
C13 | 0.4223 (3) | −0.1588 (2) | 0.21092 (19) | 0.0529 (9) | |
H13A | 0.4006 | −0.1854 | 0.2537 | 0.063* | |
C14 | 0.4651 (3) | −0.2085 (2) | 0.1574 (2) | 0.0537 (9) | |
H14A | 0.4727 | −0.2694 | 0.1629 | 0.064* | |
C15 | 0.4970 (4) | −0.1705 (2) | 0.09600 (18) | 0.0558 (9) | |
H15A | 0.5291 | −0.2047 | 0.0591 | 0.067* | |
C16 | 0.4826 (4) | −0.0828 (2) | 0.08766 (17) | 0.0568 (9) | |
H16A | 0.5028 | −0.0569 | 0.0444 | 0.068* | |
C17 | 0.6155 (3) | 0.3332 (2) | 0.06147 (14) | 0.0391 (7) | |
H17A | 0.5243 | 0.3319 | 0.0498 | 0.047* | |
C18 | 0.6894 (3) | 0.2592 (2) | 0.05372 (15) | 0.0445 (8) | |
H18A | 0.6488 | 0.2073 | 0.0375 | 0.053* | |
C19 | 0.8210 (3) | 0.2609 (2) | 0.06944 (16) | 0.0495 (8) | |
H19A | 0.8720 | 0.2101 | 0.0643 | 0.059* | |
C20 | 0.8790 (3) | 0.3359 (2) | 0.09259 (17) | 0.0522 (9) | |
H20A | 0.9706 | 0.3369 | 0.1032 | 0.063* | |
C21 | 0.8063 (3) | 0.4102 (2) | 0.10076 (16) | 0.0451 (8) | |
H21A | 0.8481 | 0.4619 | 0.1164 | 0.054* | |
C22 | 0.6723 (3) | 0.40955 (19) | 0.08613 (14) | 0.0344 (6) | |
C23 | 0.5946 (3) | 0.48889 (18) | 0.09338 (14) | 0.0344 (6) | |
C24 | 0.6553 (3) | 0.5734 (2) | 0.07503 (18) | 0.0488 (8) | |
H24A | 0.6976 | 0.5680 | 0.0301 | 0.073* | |
H24B | 0.7208 | 0.5895 | 0.1114 | 0.073* | |
H24C | 0.5874 | 0.6180 | 0.0715 | 0.073* | |
C25 | 0.2822 (3) | 0.54878 (18) | 0.10913 (14) | 0.0337 (6) | |
C26 | 0.0801 (3) | 0.6392 (2) | 0.11104 (17) | 0.0443 (8) | |
C27 | 0.0329 (3) | 0.7260 (2) | 0.08622 (15) | 0.0391 (7) | |
C28 | 0.1022 (3) | 0.8009 (2) | 0.10018 (17) | 0.0482 (8) | |
H28A | 0.1824 | 0.7984 | 0.1269 | 0.058* | |
C29 | 0.0558 (4) | 0.8797 (2) | 0.07568 (18) | 0.0590 (9) | |
H29A | 0.1040 | 0.9310 | 0.0859 | 0.071* | |
C30 | −0.0587 (4) | 0.8839 (3) | 0.0369 (2) | 0.0629 (10) | |
H30A | −0.0902 | 0.9381 | 0.0199 | 0.075* | |
C31 | −0.1284 (4) | 0.8099 (3) | 0.02259 (18) | 0.0610 (10) | |
H31A | −0.2082 | 0.8130 | −0.0044 | 0.073* | |
C32 | −0.0837 (3) | 0.7306 (2) | 0.04694 (17) | 0.0501 (8) | |
H32A | −0.1326 | 0.6796 | 0.0368 | 0.060* | |
H1N3 | 0.469 (3) | 0.094 (2) | 0.2191 (16) | 0.040 (9)* | |
H1N6 | 0.247 (3) | 0.662 (2) | 0.0807 (18) | 0.057 (11)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.0308 (2) | 0.02381 (19) | 0.0382 (2) | −0.00201 (15) | 0.00162 (14) | 0.00350 (15) |
S1 | 0.0369 (4) | 0.0279 (4) | 0.0755 (6) | −0.0047 (3) | −0.0012 (4) | 0.0022 (4) |
S2 | 0.0331 (4) | 0.0334 (4) | 0.0527 (4) | −0.0017 (3) | 0.0002 (3) | 0.0065 (3) |
O1 | 0.209 (4) | 0.0493 (16) | 0.0385 (13) | 0.043 (2) | 0.0135 (18) | 0.0059 (12) |
O2 | 0.0527 (16) | 0.0495 (15) | 0.122 (2) | 0.0062 (12) | 0.0323 (16) | 0.0261 (15) |
N1 | 0.0352 (13) | 0.0235 (12) | 0.0354 (12) | 0.0022 (10) | 0.0030 (10) | 0.0011 (9) |
N2 | 0.0444 (15) | 0.0225 (13) | 0.0408 (13) | 0.0024 (11) | 0.0020 (11) | 0.0013 (10) |
N3 | 0.0586 (18) | 0.0232 (13) | 0.0430 (15) | 0.0007 (12) | −0.0011 (13) | 0.0044 (12) |
N4 | 0.0314 (13) | 0.0277 (13) | 0.0378 (12) | 0.0001 (10) | 0.0020 (10) | 0.0028 (10) |
N5 | 0.0344 (14) | 0.0286 (13) | 0.0462 (14) | 0.0024 (11) | 0.0049 (11) | 0.0073 (10) |
N6 | 0.0382 (16) | 0.0345 (15) | 0.0592 (17) | 0.0043 (13) | 0.0111 (13) | 0.0155 (13) |
C1 | 0.0466 (19) | 0.0400 (18) | 0.0397 (16) | 0.0040 (15) | 0.0008 (14) | −0.0050 (13) |
C2 | 0.076 (3) | 0.048 (2) | 0.056 (2) | 0.021 (2) | −0.0094 (19) | −0.0111 (17) |
C3 | 0.108 (4) | 0.032 (2) | 0.070 (2) | 0.009 (2) | −0.031 (2) | −0.0107 (17) |
C4 | 0.086 (3) | 0.040 (2) | 0.083 (3) | −0.020 (2) | −0.026 (2) | 0.0003 (19) |
C5 | 0.050 (2) | 0.045 (2) | 0.064 (2) | −0.0099 (16) | −0.0082 (16) | −0.0020 (16) |
C6 | 0.0408 (17) | 0.0321 (16) | 0.0321 (14) | −0.0011 (13) | −0.0021 (12) | −0.0003 (12) |
C7 | 0.0335 (15) | 0.0321 (16) | 0.0326 (14) | 0.0006 (13) | 0.0046 (12) | 0.0008 (12) |
C8 | 0.0474 (19) | 0.045 (2) | 0.0550 (19) | 0.0114 (16) | −0.0114 (15) | −0.0040 (15) |
C9 | 0.0460 (18) | 0.0242 (15) | 0.0389 (15) | 0.0008 (13) | 0.0093 (13) | 0.0014 (12) |
C10 | 0.072 (2) | 0.0336 (18) | 0.0398 (17) | 0.0091 (16) | 0.0133 (16) | 0.0018 (14) |
C11 | 0.0477 (18) | 0.0260 (15) | 0.0411 (16) | 0.0049 (13) | 0.0005 (13) | −0.0012 (12) |
C12 | 0.0474 (19) | 0.0321 (17) | 0.0477 (17) | 0.0006 (14) | 0.0103 (14) | 0.0012 (13) |
C13 | 0.052 (2) | 0.0371 (19) | 0.070 (2) | −0.0007 (16) | 0.0124 (17) | 0.0146 (17) |
C14 | 0.051 (2) | 0.0260 (17) | 0.083 (3) | −0.0021 (15) | −0.0117 (18) | −0.0024 (17) |
C15 | 0.072 (2) | 0.040 (2) | 0.055 (2) | 0.0129 (17) | −0.0132 (18) | −0.0175 (16) |
C16 | 0.089 (3) | 0.043 (2) | 0.0389 (17) | 0.0126 (19) | −0.0001 (17) | −0.0044 (15) |
C17 | 0.0364 (16) | 0.0485 (19) | 0.0327 (14) | −0.0001 (14) | 0.0056 (12) | −0.0008 (13) |
C18 | 0.054 (2) | 0.0422 (19) | 0.0374 (16) | 0.0025 (16) | 0.0067 (14) | −0.0032 (13) |
C19 | 0.054 (2) | 0.051 (2) | 0.0435 (17) | 0.0151 (17) | 0.0088 (15) | 0.0042 (15) |
C20 | 0.0327 (17) | 0.067 (2) | 0.057 (2) | 0.0062 (17) | 0.0055 (15) | 0.0032 (18) |
C21 | 0.0358 (17) | 0.049 (2) | 0.0511 (18) | −0.0033 (15) | 0.0059 (14) | 0.0011 (15) |
C22 | 0.0340 (16) | 0.0389 (17) | 0.0309 (14) | −0.0002 (13) | 0.0074 (12) | 0.0039 (12) |
C23 | 0.0341 (16) | 0.0353 (16) | 0.0340 (14) | −0.0030 (13) | 0.0026 (12) | 0.0041 (12) |
C24 | 0.0421 (19) | 0.0419 (19) | 0.063 (2) | −0.0059 (15) | 0.0133 (16) | 0.0101 (16) |
C25 | 0.0370 (17) | 0.0304 (16) | 0.0341 (14) | 0.0039 (13) | 0.0068 (12) | 0.0065 (12) |
C26 | 0.0406 (18) | 0.0385 (18) | 0.0542 (19) | 0.0018 (14) | 0.0093 (15) | 0.0042 (14) |
C27 | 0.0345 (16) | 0.0404 (18) | 0.0431 (16) | 0.0049 (14) | 0.0101 (13) | 0.0025 (13) |
C28 | 0.049 (2) | 0.044 (2) | 0.0521 (18) | 0.0039 (16) | −0.0020 (15) | −0.0012 (15) |
C29 | 0.077 (3) | 0.038 (2) | 0.062 (2) | 0.0052 (19) | 0.006 (2) | −0.0033 (16) |
C30 | 0.075 (3) | 0.050 (2) | 0.064 (2) | 0.022 (2) | 0.009 (2) | 0.0128 (18) |
C31 | 0.047 (2) | 0.079 (3) | 0.057 (2) | 0.018 (2) | 0.0037 (17) | 0.0150 (19) |
C32 | 0.0397 (18) | 0.053 (2) | 0.058 (2) | −0.0003 (16) | 0.0060 (15) | 0.0043 (16) |
Ni1—N4 | 1.922 (2) | C11—C16 | 1.381 (4) |
Ni1—N1 | 1.928 (2) | C12—C13 | 1.381 (4) |
Ni1—S2 | 2.1489 (10) | C12—H12A | 0.9500 |
Ni1—S1 | 2.1518 (10) | C13—C14 | 1.366 (5) |
S1—C9 | 1.728 (3) | C13—H13A | 0.9500 |
S2—C25 | 1.735 (3) | C14—C15 | 1.365 (5) |
O1—C10 | 1.204 (4) | C14—H14A | 0.9500 |
O2—C26 | 1.210 (4) | C15—C16 | 1.374 (5) |
N1—C7 | 1.293 (3) | C15—H15A | 0.9500 |
N1—N2 | 1.407 (3) | C16—H16A | 0.9500 |
N2—C9 | 1.275 (4) | C17—C18 | 1.383 (4) |
N3—C10 | 1.359 (4) | C17—C22 | 1.391 (4) |
N3—C9 | 1.411 (4) | C17—H17A | 0.9500 |
N3—H1N3 | 0.78 (3) | C18—C19 | 1.367 (4) |
N4—C23 | 1.294 (3) | C18—H18A | 0.9500 |
N4—N5 | 1.408 (3) | C19—C20 | 1.369 (5) |
N5—C25 | 1.279 (4) | C19—H19A | 0.9500 |
N6—C26 | 1.356 (4) | C20—C21 | 1.381 (5) |
N6—C25 | 1.399 (4) | C20—H20A | 0.9500 |
N6—H1N6 | 0.80 (3) | C21—C22 | 1.387 (4) |
C1—C2 | 1.379 (5) | C21—H21A | 0.9500 |
C1—C6 | 1.379 (4) | C22—C23 | 1.471 (4) |
C1—H1A | 0.9500 | C23—C24 | 1.494 (4) |
C2—C3 | 1.366 (6) | C24—H24A | 0.9800 |
C2—H2A | 0.9500 | C24—H24B | 0.9800 |
C3—C4 | 1.361 (6) | C24—H24C | 0.9800 |
C3—H3A | 0.9500 | C26—C27 | 1.497 (4) |
C4—C5 | 1.380 (5) | C27—C28 | 1.380 (4) |
C4—H4A | 0.9500 | C27—C32 | 1.387 (4) |
C5—C6 | 1.388 (4) | C28—C29 | 1.383 (5) |
C5—H5A | 0.9500 | C28—H28A | 0.9500 |
C6—C7 | 1.472 (4) | C29—C30 | 1.364 (5) |
C7—C8 | 1.491 (4) | C29—H29A | 0.9500 |
C8—H8A | 0.9800 | C30—C31 | 1.371 (5) |
C8—H8B | 0.9800 | C30—H30A | 0.9500 |
C8—H8C | 0.9800 | C31—C32 | 1.383 (5) |
C10—C11 | 1.490 (4) | C31—H31A | 0.9500 |
C11—C12 | 1.375 (4) | C32—H32A | 0.9500 |
N4—Ni1—N1 | 101.23 (10) | C14—C13—H13A | 119.7 |
N4—Ni1—S2 | 86.18 (7) | C12—C13—H13A | 119.7 |
N1—Ni1—S2 | 159.86 (7) | C15—C14—C13 | 119.9 (3) |
N4—Ni1—S1 | 159.67 (7) | C15—C14—H14A | 120.1 |
N1—Ni1—S1 | 85.99 (7) | C13—C14—H14A | 120.1 |
S2—Ni1—S1 | 93.44 (4) | C14—C15—C16 | 119.8 (3) |
C9—S1—Ni1 | 94.53 (10) | C14—C15—H15A | 120.1 |
C25—S2—Ni1 | 94.14 (10) | C16—C15—H15A | 120.1 |
C7—N1—N2 | 114.1 (2) | C15—C16—C11 | 121.1 (3) |
C7—N1—Ni1 | 127.91 (19) | C15—C16—H16A | 119.5 |
N2—N1—Ni1 | 118.01 (17) | C11—C16—H16A | 119.5 |
C9—N2—N1 | 111.4 (2) | C18—C17—C22 | 121.1 (3) |
C10—N3—C9 | 123.6 (3) | C18—C17—H17A | 119.4 |
C10—N3—H1N3 | 116 (2) | C22—C17—H17A | 119.4 |
C9—N3—H1N3 | 116 (2) | C19—C18—C17 | 119.8 (3) |
C23—N4—N5 | 114.1 (2) | C19—C18—H18A | 120.1 |
C23—N4—Ni1 | 128.18 (19) | C17—C18—H18A | 120.1 |
N5—N4—Ni1 | 117.74 (17) | C18—C19—C20 | 119.9 (3) |
C25—N5—N4 | 111.3 (2) | C18—C19—H19A | 120.1 |
C26—N6—C25 | 129.9 (3) | C20—C19—H19A | 120.1 |
C26—N6—H1N6 | 117 (3) | C19—C20—C21 | 120.9 (3) |
C25—N6—H1N6 | 113 (3) | C19—C20—H20A | 119.5 |
C2—C1—C6 | 120.8 (3) | C21—C20—H20A | 119.5 |
C2—C1—H1A | 119.6 | C20—C21—C22 | 120.2 (3) |
C6—C1—H1A | 119.6 | C20—C21—H21A | 119.9 |
C3—C2—C1 | 119.8 (4) | C22—C21—H21A | 119.9 |
C3—C2—H2A | 120.1 | C21—C22—C17 | 118.1 (3) |
C1—C2—H2A | 120.1 | C21—C22—C23 | 120.5 (3) |
C4—C3—C2 | 120.5 (3) | C17—C22—C23 | 121.4 (3) |
C4—C3—H3A | 119.8 | N4—C23—C22 | 119.5 (2) |
C2—C3—H3A | 119.8 | N4—C23—C24 | 122.0 (3) |
C3—C4—C5 | 120.1 (4) | C22—C23—C24 | 118.5 (2) |
C3—C4—H4A | 119.9 | C23—C24—H24A | 109.5 |
C5—C4—H4A | 119.9 | C23—C24—H24B | 109.5 |
C4—C5—C6 | 120.3 (4) | H24A—C24—H24B | 109.5 |
C4—C5—H5A | 119.8 | C23—C24—H24C | 109.5 |
C6—C5—H5A | 119.8 | H24A—C24—H24C | 109.5 |
C1—C6—C5 | 118.5 (3) | H24B—C24—H24C | 109.5 |
C1—C6—C7 | 120.5 (3) | N5—C25—N6 | 113.7 (3) |
C5—C6—C7 | 120.9 (3) | N5—C25—S2 | 124.9 (2) |
N1—C7—C6 | 119.4 (2) | N6—C25—S2 | 121.2 (2) |
N1—C7—C8 | 122.1 (3) | O2—C26—N6 | 123.0 (3) |
C6—C7—C8 | 118.5 (2) | O2—C26—C27 | 123.4 (3) |
C7—C8—H8A | 109.5 | N6—C26—C27 | 113.7 (3) |
C7—C8—H8B | 109.5 | C28—C27—C32 | 119.1 (3) |
H8A—C8—H8B | 109.5 | C28—C27—C26 | 122.3 (3) |
C7—C8—H8C | 109.5 | C32—C27—C26 | 118.6 (3) |
H8A—C8—H8C | 109.5 | C27—C28—C29 | 120.5 (3) |
H8B—C8—H8C | 109.5 | C27—C28—H28A | 119.7 |
N2—C9—N3 | 115.7 (3) | C29—C28—H28A | 119.7 |
N2—C9—S1 | 125.1 (2) | C30—C29—C28 | 120.2 (4) |
N3—C9—S1 | 119.1 (2) | C30—C29—H29A | 119.9 |
O1—C10—N3 | 121.3 (3) | C28—C29—H29A | 119.9 |
O1—C10—C11 | 122.5 (3) | C29—C30—C31 | 119.8 (3) |
N3—C10—C11 | 116.2 (3) | C29—C30—H30A | 120.1 |
C12—C11—C16 | 118.6 (3) | C31—C30—H30A | 120.1 |
C12—C11—C10 | 122.7 (3) | C30—C31—C32 | 120.7 (3) |
C16—C11—C10 | 118.6 (3) | C30—C31—H31A | 119.7 |
C11—C12—C13 | 120.0 (3) | C32—C31—H31A | 119.7 |
C11—C12—H12A | 120.0 | C31—C32—C27 | 119.7 (3) |
C13—C12—H12A | 120.0 | C31—C32—H32A | 120.2 |
C14—C13—C12 | 120.6 (3) | C27—C32—H32A | 120.2 |
C7—N1—N2—C9 | 161.4 (2) | C12—C11—C16—C15 | 0.0 (5) |
Ni1—N1—N2—C9 | −19.0 (3) | C10—C11—C16—C15 | −178.6 (3) |
C23—N4—N5—C25 | 159.4 (2) | C22—C17—C18—C19 | −1.0 (4) |
Ni1—N4—N5—C25 | −20.2 (3) | C17—C18—C19—C20 | −0.2 (5) |
C6—C1—C2—C3 | 0.0 (5) | C18—C19—C20—C21 | 0.4 (5) |
C1—C2—C3—C4 | −0.3 (6) | C19—C20—C21—C22 | 0.6 (5) |
C2—C3—C4—C5 | −0.3 (6) | C20—C21—C22—C17 | −1.7 (4) |
C3—C4—C5—C6 | 1.2 (6) | C20—C21—C22—C23 | −178.8 (3) |
C2—C1—C6—C5 | 1.0 (4) | C18—C17—C22—C21 | 1.9 (4) |
C2—C1—C6—C7 | 177.5 (3) | C18—C17—C22—C23 | 179.0 (2) |
C4—C5—C6—C1 | −1.6 (5) | N5—N4—C23—C22 | −171.8 (2) |
C4—C5—C6—C7 | −178.1 (3) | Ni1—N4—C23—C22 | 7.8 (4) |
N2—N1—C7—C6 | −171.0 (2) | N5—N4—C23—C24 | 7.0 (4) |
Ni1—N1—C7—C6 | 9.4 (4) | Ni1—N4—C23—C24 | −173.5 (2) |
N2—N1—C7—C8 | 6.9 (4) | C21—C22—C23—N4 | −145.6 (3) |
Ni1—N1—C7—C8 | −172.7 (2) | C17—C22—C23—N4 | 37.4 (4) |
C1—C6—C7—N1 | 41.4 (4) | C21—C22—C23—C24 | 35.6 (4) |
C5—C6—C7—N1 | −142.2 (3) | C17—C22—C23—C24 | −141.4 (3) |
C1—C6—C7—C8 | −136.6 (3) | N4—N5—C25—N6 | −174.2 (2) |
C5—C6—C7—C8 | 39.8 (4) | N4—N5—C25—S2 | 1.9 (3) |
N1—N2—C9—N3 | −174.0 (2) | C26—N6—C25—N5 | −161.8 (3) |
N1—N2—C9—S1 | 2.2 (3) | C26—N6—C25—S2 | 21.9 (5) |
C10—N3—C9—N2 | −121.1 (3) | Ni1—S2—C25—N5 | 13.3 (3) |
C10—N3—C9—S1 | 62.5 (4) | Ni1—S2—C25—N6 | −170.8 (2) |
Ni1—S1—C9—N2 | 12.1 (3) | C25—N6—C26—O2 | 5.6 (6) |
Ni1—S1—C9—N3 | −171.8 (2) | C25—N6—C26—C27 | −174.9 (3) |
C9—N3—C10—O1 | −5.5 (6) | O2—C26—C27—C28 | 131.8 (4) |
C9—N3—C10—C11 | 173.7 (3) | N6—C26—C27—C28 | −47.7 (4) |
O1—C10—C11—C12 | −152.7 (4) | O2—C26—C27—C32 | −49.2 (5) |
N3—C10—C11—C12 | 28.1 (5) | N6—C26—C27—C32 | 131.3 (3) |
O1—C10—C11—C16 | 25.8 (6) | C32—C27—C28—C29 | 0.3 (5) |
N3—C10—C11—C16 | −153.4 (3) | C26—C27—C28—C29 | 179.3 (3) |
C16—C11—C12—C13 | −1.4 (5) | C27—C28—C29—C30 | −0.4 (5) |
C10—C11—C12—C13 | 177.1 (3) | C28—C29—C30—C31 | 0.3 (6) |
C11—C12—C13—C14 | 1.3 (5) | C29—C30—C31—C32 | −0.1 (6) |
C12—C13—C14—C15 | 0.3 (5) | C30—C31—C32—C27 | −0.1 (5) |
C13—C14—C15—C16 | −1.7 (5) | C28—C27—C32—C31 | 0.0 (5) |
C14—C15—C16—C11 | 1.6 (6) | C26—C27—C32—C31 | −179.1 (3) |
Cg1 is the centroid of the C27–C32 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C16—H16A···O1i | 0.95 | 2.51 | 3.306 (5) | 141 |
C21—H21A···O2ii | 0.95 | 2.60 | 3.522 (4) | 165 |
C19—H19A···Cg1iii | 0.95 | 2.86 | 3.400 (4) | 117 |
Symmetry codes: (i) −x+1, −y, −z; (ii) x+1, y, z; (iii) −x+1, −y+1, −z. |
Ni1—N4 | 1.922 (2) | S1—C9 | 1.728 (3) |
Ni1—N1 | 1.928 (2) | S2—C25 | 1.735 (3) |
Ni1—S2 | 2.1489 (10) | N1—C7 | 1.293 (3) |
Ni1—S1 | 2.1518 (10) | N4—C23 | 1.294 (3) |
N4—Ni1—N1 | 101.23 (10) | N4—Ni1—S1 | 159.67 (7) |
N4—Ni1—S2 | 86.18 (7) | N1—Ni1—S1 | 85.99 (7) |
N1—Ni1—S2 | 159.86 (7) | S2—Ni1—S1 | 93.44 (4) |
Cg1 is the centroid of the C27–C32 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C16—H16A···O1i | 0.9500 | 2.5100 | 3.306 (5) | 141.00 |
C21—H21A···O2ii | 0.9500 | 2.6000 | 3.522 (4) | 165.00 |
C19—H19A···Cg1iii | 0.9500 | 2.8600 | 3.400 (4) | 117.00 |
Symmetry codes: (i) −x+1, −y, −z; (ii) x+1, y, z; (iii) −x+1, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | [Ni(C16H14N3OS)2] |
Mr | 651.43 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 297 |
a, b, c (Å) | 10.220 (3), 15.468 (5), 19.151 (6) |
β (°) | 92.150 (5) |
V (Å3) | 3025.1 (17) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.82 |
Crystal size (mm) | 0.19 × 0.18 × 0.09 |
Data collection | |
Diffractometer | Bruker APEX DUO CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2009) |
No. of measured, independent and observed [I > 2σ(I)] reflections | 43914, 5893, 4635 |
Rint | 0.070 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.100, 1.05 |
No. of reflections | 5893 |
No. of parameters | 398 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.46, −0.38 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL2014 (Sheldrick, 2015), PLATON (Spek, 2009) and publCIF (Westrip, 2010).
Footnotes
‡Additional correspondence author, e-mail: mustaffa@kimia.fs.utm.my.
Acknowledgements
The authors thank the Universiti Teknologi Malaysia (UTM) for financial support through vote numbers 03H06 & 03H81 and the Kurdistan Regional Government–Human Capacity Development Program (KRG–HCDP) for the scholarship to FKK.
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