The title Schiff base compound, consisting of a cyclohexane and a 2-hydroxy-3-methylbenzylidene ring bridged by a hydrazinecarbothioamine moiety, crystallizes with two independent molecules in the asymmetric unit. In the crystal, the molecules are linked by N—H⋯S hydrogen bonds and C—H⋯π interactions, forming ribbons along the [010] direction.
Keywords: crystal structure, hydrazinecarbothioamide, Schiff base, intermolecular interactions
Abstract
The asymmetric unit of the title compound, C15H21N3OS, comprises of two crystallographically independent molecules (A and B). Each molecule consists of a cyclohexane ring and a 2-hydroxy-3-methylbenzylidene ring bridged by a hydrazinecarbothioamine unit. Both molecules exhibit an E configuration with respect to the azomethine C=N bond. There is an intramolecular O—H⋯N hydrogen bond in each molecule forming an S(6) ring motif. The cyclohexane ring in each molecule has a chair conformation. The benzene ring is inclined to the mean plane of the cyclohexane ring by 47.75 (9)° in molecule A and 66.99 (9)° in molecule B. The mean plane of the cyclohexane ring is inclined to the mean plane of the thiourea moiety [N—C(=S)—N] by 55.69 (9) and 58.50 (8)° in molecules A and B, respectively. In the crystal, the A and B molecules are linked by N—H⋯S hydrogen bonds, forming ‘dimers’. The A molecules are further linked by a C—H⋯π interaction, hence linking the A–B units to form ribbons propagating along the b-axis direction. The conformation of a number of related cyclohexanehydrazinecarbothioamides are compared to that of the title compound.
Chemical context
Schiff bases are significant agents in both organic and inorganic chemistry, and are widely used in biological applications, particularly for anticancer screening (Ziessel, 2001 ▸; Salam et al., 2012a ▸; Arafath et al., 2017b ▸). They have attracted a great deal of attention because of the presence of hard and soft atoms together in one molecule. Thiosemicarbazone Schiff base compounds have soft sulfur and hard nitrogen as well hard oxygen atoms (Mohamed et al., 2009 ▸). These Schiff base compounds are of special interest because of their diversity in coordinating to hard and soft metals using the hard and soft coordinating sites such as NSO (Arion et al., 2001 ▸; Leovac & Češljević, 2002 ▸; Chandra & Sangeetika, 2004 ▸; Singh et al., 2000 ▸; Gerbeleu et al., 2008 ▸; Mohamed et al., 2009 ▸). Many Schiff base compounds and their complexes with transition metals have wide biological and pharmaceutical applications (Padhyé & Kauffman, 1985 ▸; Salam et al., 2012b ▸). Thiosemicarbazones having ONS-coordinating sites are important for coordination chemistry because of their strong bonding ability with transition metals (Rayati et al., 2007 ▸; Alomar et al., 2009 ▸; Vieites et al., 2009 ▸; Siddiki et al., 2012 ▸).
Structural commentary
The asymmetric unit of the title compound consists of two crystallographic independent molecules (A and B), as illustrated in Fig. 1 ▸. In each molecule a cyclohexane ring and a 2-hydroxy-3-methylbenzylidene ring are interconnected by a hydrazinecarbothioamine bridge. Both molecules exhibit an E configuration with respect to the azomethine C7=N1 bond, and in each molecule there is an intramolecular O—H⋯N hydrogen bond forming an S(6) ring motif (Table 1 ▸and Fig. 1 ▸). The best AutoMolFit (PLATON; Spek, 2009 ▸) image of the two molecules, viz. inverted molecule B (red) on molecule A (black), which has an r.m.s. deviation of 0.654 Å, is shown in Fig. 2 ▸.
Figure 1.
A view of the molecular structure of the two independent molecules (A and B) of the title compound, with the atom labelling. Displacement ellipsoids are drawn at the 50% probability level. The intramolecular O—H⋯N hydrogen bonds (Table 1 ▸) are shown as dashed cyan lines.
Table 1. Hydrogen-bond geometry (Å, °).
Cg1 is the centroid of benzene ring C1A–C6A.
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| O1A—H1O1⋯N1A | 0.80 (2) | 1.98 (2) | 2.6844 (19) | 146 (2) |
| O1B—H1O2⋯N1B | 0.84 (2) | 1.91 (2) | 2.664 (2) | 148 (2) |
| N2A—H1N2⋯S1B i | 0.85 (2) | 2.60 (2) | 3.4414 (16) | 170 (2) |
| N2B—H2N2⋯S1A i | 0.85 (2) | 2.53 (2) | 3.3568 (15) | 164 (2) |
| C11A—H11B⋯Cg1ii | 0.99 | 2.93 | 3.801 (2) | 148 |
Symmetry codes: (i) 
; (ii) 
.
Figure 2.
An AutoMolFit figure (PLATON; Spek, 2009 ▸) of inverted molecule B (red) on molecule A (black).
The cyclohexane ring (C9–C14) in each molecule has a chair conformation. The mean plane of the four central C atoms (C10/C11/C13/C14) is inclined to the mean plane of the thiourea moiety [N2—C8(=S1)—N3] by 54.83 (11) and 55.64 (10)° in molecules A and B, respectively, and by 50.33 (10) and 65.30 (10)° to the benzene rings (C1–C6) in molecules A and B, respectively. The benzene ring is inclined to the mean plane of the thiourea moiety by 10.95 (8)° in molecule A and 9.80 (8)° in molecule B.
The unique molecular conformations of the two molecules can be characterized by five torsion angles, i.e. τ 1 (C1—C6—C7—N1), τ 2 (C7—N1—N2—C8), τ 3 (N1—N2—C8—N3), τ 4 (N2—C8—N3—C9) and τ 5 (C8—N3—C9—C10), as illustrated in Fig. 3 ▸. The torsion angle τ 1 between the benzylidine ring and the azomethine double bond for both molecules are approximately 0° [3.0 (2)° in molecule A and 1.9 (2)° in molecule B], signifying the coplanarity between benzylidine ring and the azomethine double bond (C7=N1). In molecule B, the azomethine double bond is close to planar with the hydrazine moiety [τ 2 = 177.23 (14)°], whereas τ 2 in molecule A is slightly twisted [τ 2 = 171.68 (14)°]. In both molecules, the torsion angle between the hydrazine moiety and the carbothio group are also slight twisted with τ 3 values in molecules A and B of 7.4 (2) and −10.2 (2)°, respectively. Similarly to τ 1, the carbothio group is almost coplanar with the thioamide group for both molecules, as implied by torsion angle τ 4 [178.07 (14)° in molecule A and 175.59 (14)° in molecule B], which are approximately 180°. The thioamide group and the cyclohexane ring are almost perpendicular to each other with τ 5 torsion angles of 85.3 (2) and −81.6 (2)° in molecules A and B, respectively. This may arise from the steric repulsion between the cyclohexane ring and adjacent sulfur atom.
Figure 3.
General chemical diagram showing torsion angles, τ 1, τ 2, τ 3, τ 4 and τ 5 in the title compound.
Supramolecular features
In the crystal, the A and B molecules are connected into ‘dimers’ with an 
(8) ring motif, via N2A—H1N2⋯S1B
i and N2B—H2N2⋯S1A
i hydrogen bonds (Fig. 4 ▸ and Table 1 ▸). The A molecules are further linked by a C—H⋯π interaction, so linking the A–B units to form ribbons propagating along the b-axis direction, as illustrated in Fig. 4 ▸.
Figure 4.
A partial view, normal to the ac plane, of the crystal packing of the title compound. The N—H⋯S hydrogen bonds are shown as cyan dotted lines, and the C—H⋯ π interactions as green dotted lines (see Table 1 ▸ for details). For clarity, only the hydrogen atoms involved in these interactions have been included.
Database survey
A search of the Cambridge Structural Database (CSD version 5.40, last update February 2019; Groom et al., 2016 ▸) using (E)-2-benzylidene-N-cyclohexylhydrazine-1-carbothioamide as the reference moiety resulted in nine structures containing a cyclohexylhydrazinecarbothioamide moiety with different substituents (R). The different substituents (R) together with the torsion angles of the hydrazinecarbothioamide connecting bridge are compiled in Table 2 ▸ (cf. Fig. 3 ▸). In these structures, including the title compound, the hydrazinecarbothioamide connecting bridge is nearly planar as τ 2, τ 3 and τ 4 are in, respectively, anti-periplanar (153.5 to 179.3°), syn-periplanar (0.8 to 14.7°) and anti-periplanar (from 171.8 to 180.0°) conformations. The attached cyclohexane ring is always close to perpendicular to the thioamide group and with a syn/anti-clinal (τ 5 = 78.3 to 94.5°) conformation. Furthermore, torsion angle τ 1 for most of these structures exists in a syn-periplanar conformation, ranging from 0 to 25.8°, but there is one outlier (molecule B in NALKOD; Basheer et al., 2016b ▸) where torsion angle τ 1 is in a syn-clinal (36.2°) conformation. The cyclohexylhydrazinecarbothioamide moiety of this structure is substituted with an anthracen-9-ylmethylene ring system.
Table 2. Torsion angles τ1, τ2, τ3, τ4 and τ5 (°).
| Compound | R | τ1 | τ2 | τ3 | τ4 | τ5 |
|---|---|---|---|---|---|---|
| Title compound | 2-hydroxy-3-methylbenzylidene | 3.2, 1.9 | 171.7, 177.2 | 7.4, 10.2 | 178.1, 175.6 | 85.3, 81.6 |
| ABUHEN (Basheer et al., 2017 ▸) | pyren-1-ylmethylene | 10.1 | 174.9 | 1.2 | 180.0 | 81.6 |
| BEFZIY (Basheer et al., 2016a ▸) | 2-hydroxy-1-naphthyl)methylene | 0.9 | 179.3 | 6.8 | 176.6 | 83.4 |
| BEVNAR (Koo et al., 1981 ▸) | 4-aminobenzylidene | 14.3 | 175.0 | 7.4 | 178.5 | 94.5 |
| LAQCIR (Jacob & Kurup, 2012 ▸) | 5-bromo-2-hydroxy-3-methoxybenzylidene | 10.1 | 176.8 | 4.1 | 179.5 | 86.2 |
| LEPFIW (Seena et al., 2006 ▸) | 1-(2-hydroxyphenyl)ethylidene | 3.9, 6.6 | 155.0, 153.5 | 14.0, 14.7 | 175.7, 171.8 | 91.9, 81.6 |
| NALKOD (Basheer et al., 2016b ▸) | anthracen-9-ylmethylene | 25.8, 36.2 | 171.6, 178.6 | 0.8, 1.4 | 172.9, 176.2 | 79.0, 79.2 |
| OBOLOJ (Arafath, 2017a ▸) | 5-chloro-2-hydroxybenzylidene | 4.7 | 176.0 | 5.5 | 176.7 | 83.7 |
| XOYKAZ (Bhat et al., 2015 ▸) | 4-ethoxybenzylidene | 0.5 | 169.3 | 11.6 | 176.2 | 85.8 |
| YUXJOS (Arafath et al., 2018 ▸) | 3-t-butyl-2-hydroxyphenyl)methylidene | 11.8 | 170.1 | 12.5 | 176.2 | 78.3 |
Note: The title compound and compounds LEPFIW and NALKOD crystallize with two independent molecules in the asymmetric unit.
Synthesis and crystallization
The reaction scheme for the synthesis of the title Schiff base compound is given in Fig. 5 ▸.
Figure 5.
Reaction scheme for the synthesis of the title compound.
2-Hydroxy-3-methylbenzaldehyde (0.68 g, 5.00 mmol) was dissolved in 20 ml of methanol. Glacial acetic acid (0.20 ml) was added and the mixture was refluxed for 30 min. A solution of N-cyclohexylhydrazine carbothioamide (0.87 g, 5 mmol) in 20 ml methanol was added dropwise with stirring to the aldehyde solution. The resulting colourless solution was refluxed for 4 h with stirring. A colourless precipitate was obtained on evaporation of the solvent. The crude product was washed with n-hexane (5 ml). The recovered product was dissolved in acetonitrile and purified by recrystallization. Colourless block-like crystals suitable for X-ray diffraction analysis were obtained on slow evaporation of the acetonitrile solvent (m.p. 513–514 K, yield 93%).
Spectroscopic and analytical data: 1H NMR (500 MHz, DMSO-d 6, Me4Si ppm): δ 11.27 (s, N—NH), δ 9.51 (s, OH), δ 8.34 (s, HC=N), δ 8.05 (d, J = 8.35 Hz, CS=NH), δ 7.39–6.81 (multiplet, aromatic-H), δ 2.20 (s, Ph—CH3), δ 1.87–1.14 (multiplet, cyclohexyl-H) ppm. 13C NMR (DMSO-d 6, Me4Si ppm): δ 175.79 (C=S), δ 154.29 (C=N), δ 143.76-119.17 (C-aromatic), δ 15.93 (CH3), δ 52.87–24.90 (C-cyclohexyl) ppm. IR (KBr pellets, cm−1): 3364 (NH), 3148 (OH), 2989(CH3), 2931 and 2854 (CH, cyclohexyl), 1620 (C=N), 1540 (C=C, aromatic), 1268 (C=S), 1218 (CH, bend., aromatic), 1122 (C—O). 1075 (C—N). Elemental analysis calculated for C15H21N3OS (M r = 291.41 g mol−1); C, 61.77; H, 7.21; N, 14.42%; found: C, 61.81; H, 7.19; N, 14.42%.
Refinement
Crystal data, data collection and structure refinement details are summarized in Table 3 ▸. The O and N-bound H atoms were located in a difference-Fourier map and freely refined. The C-bound H atoms were positioned geometrically and refined using a riding model: C—H = 0.95–1.00 Å with U iso(H) = 1.5U eq(C-methyl) and 1.2U eq(C) for other H atoms.
Table 3. Experimental details.
| Crystal data | |
| Chemical formula | C15H21N3OS |
| M r | 291.41 |
| Crystal system, space group | Triclinic, P
|
| Temperature (K) | 100 |
| a, b, c (Å) | 10.7799 (11), 10.9481 (11), 14.1895 (15) |
| α, β, γ (°) | 74.526 (2), 68.246 (1), 80.207 (2) |
| V (Å3) | 1494.2 (3) |
| Z | 4 |
| Radiation type | Mo Kα |
| μ (mm−1) | 0.22 |
| Crystal size (mm) | 0.34 × 0.14 × 0.10 |
| Data collection | |
| Diffractometer | Bruker APEXII CCD |
| Absorption correction | Multi-scan (SADABS; Bruker, 2012 ▸) |
| T min, T max | 0.873, 0.935 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 50505, 8135, 5805 |
| R int | 0.069 |
| (sin θ/λ)max (Å−1) | 0.690 |
| Refinement | |
| R[F 2 > 2σ(F 2)], wR(F 2), S | 0.049, 0.119, 1.04 |
| No. of reflections | 8135 |
| No. of parameters | 387 |
| H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
| Δρmax, Δρmin (e Å−3) | 0.42, −0.36 |
Supplementary Material
Crystal structure: contains datablock(s) I, Global. DOI: 10.1107/S2056989019008946/su5501sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989019008946/su5501Isup2.hkl
CCDC reference: 1480651
Additional supporting information: crystallographic information; 3D view; checkCIF report
supplementary crystallographic information
Crystal data
| C15H21N3OS | Z = 4 |
| Mr = 291.41 | F(000) = 624 |
| Triclinic, P1 | Dx = 1.295 Mg m−3 |
| a = 10.7799 (11) Å | Mo Kα radiation, λ = 0.71073 Å |
| b = 10.9481 (11) Å | Cell parameters from 6929 reflections |
| c = 14.1895 (15) Å | θ = 2.2–29.3° |
| α = 74.526 (2)° | µ = 0.22 mm−1 |
| β = 68.246 (1)° | T = 100 K |
| γ = 80.207 (2)° | Block, colourless |
| V = 1494.2 (3) Å3 | 0.34 × 0.14 × 0.10 mm |
Data collection
| Bruker APEXII CCD diffractometer | 5805 reflections with I > 2σ(I) |
| φ and ω scans | Rint = 0.069 |
| Absorption correction: multi-scan (SADABS; Bruker, 2012) | θmax = 29.4°, θmin = 1.6° |
| Tmin = 0.873, Tmax = 0.935 | h = −14→14 |
| 50505 measured reflections | k = −15→15 |
| 8135 independent reflections | l = −19→19 |
Refinement
| 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)] = 0.049 | Hydrogen site location: mixed |
| wR(F2) = 0.119 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.03 | w = 1/[σ2(Fo2) + (0.0524P)2 + 0.3685P] where P = (Fo2 + 2Fc2)/3 |
| 8135 reflections | (Δ/σ)max = 0.001 |
| 387 parameters | Δρmax = 0.42 e Å−3 |
| 0 restraints | Δρmin = −0.36 e Å−3 |
Special details
| 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| S1A | 0.69733 (4) | 0.60902 (4) | 0.10987 (3) | 0.01869 (11) | |
| O1A | 0.20574 (12) | 0.29193 (12) | 0.27567 (9) | 0.0204 (3) | |
| H1O1 | 0.264 (2) | 0.340 (2) | 0.2474 (19) | 0.047 (7)* | |
| N1A | 0.44459 (13) | 0.36989 (12) | 0.14267 (10) | 0.0157 (3) | |
| N2A | 0.54998 (14) | 0.44583 (13) | 0.10122 (11) | 0.0168 (3) | |
| H1N2 | 0.617 (2) | 0.4267 (19) | 0.0507 (16) | 0.032 (6)* | |
| N3A | 0.45512 (13) | 0.54155 (13) | 0.23929 (11) | 0.0180 (3) | |
| H1N3 | 0.387 (2) | 0.5075 (19) | 0.2500 (16) | 0.031 (6)* | |
| C1A | 0.23068 (15) | 0.20058 (15) | 0.22090 (12) | 0.0166 (3) | |
| C2A | 0.13421 (16) | 0.11183 (15) | 0.25585 (13) | 0.0180 (3) | |
| C3A | 0.15680 (17) | 0.01785 (16) | 0.20070 (13) | 0.0212 (4) | |
| H3AA | 0.0925 | −0.0427 | 0.2231 | 0.025* | |
| C4A | 0.27061 (17) | 0.00986 (16) | 0.11389 (14) | 0.0219 (4) | |
| H4AA | 0.2840 | −0.0557 | 0.0779 | 0.026* | |
| C5A | 0.36387 (17) | 0.09792 (16) | 0.08048 (13) | 0.0204 (3) | |
| H5AA | 0.4412 | 0.0933 | 0.0206 | 0.024* | |
| C6A | 0.34648 (16) | 0.19418 (15) | 0.13340 (12) | 0.0163 (3) | |
| C7A | 0.45032 (16) | 0.28267 (15) | 0.09523 (13) | 0.0173 (3) | |
| H7AA | 0.5243 | 0.2759 | 0.0337 | 0.021* | |
| C8A | 0.55885 (15) | 0.52858 (15) | 0.15423 (12) | 0.0154 (3) | |
| C9A | 0.44553 (15) | 0.62215 (16) | 0.30920 (12) | 0.0175 (3) | |
| H9AA | 0.5368 | 0.6226 | 0.3119 | 0.021* | |
| C10A | 0.39567 (17) | 0.75839 (16) | 0.27188 (14) | 0.0223 (4) | |
| H10A | 0.3072 | 0.7594 | 0.2653 | 0.027* | |
| H10B | 0.4588 | 0.7950 | 0.2024 | 0.027* | |
| C11A | 0.38338 (17) | 0.83900 (17) | 0.34832 (14) | 0.0249 (4) | |
| H11A | 0.4734 | 0.8448 | 0.3495 | 0.030* | |
| H11B | 0.3465 | 0.9261 | 0.3246 | 0.030* | |
| C12A | 0.29295 (17) | 0.78223 (19) | 0.45741 (15) | 0.0300 (4) | |
| H12A | 0.2924 | 0.8328 | 0.5059 | 0.036* | |
| H12B | 0.2002 | 0.7864 | 0.4580 | 0.036* | |
| C13A | 0.3395 (2) | 0.64536 (19) | 0.49414 (14) | 0.0334 (5) | |
| H13A | 0.2742 | 0.6092 | 0.5627 | 0.040* | |
| H13B | 0.4269 | 0.6425 | 0.5031 | 0.040* | |
| C14A | 0.35411 (18) | 0.56458 (17) | 0.41752 (13) | 0.0253 (4) | |
| H14A | 0.3914 | 0.4777 | 0.4415 | 0.030* | |
| H14B | 0.2648 | 0.5581 | 0.4153 | 0.030* | |
| C15A | 0.01137 (16) | 0.12174 (18) | 0.34918 (14) | 0.0246 (4) | |
| H15A | −0.0495 | 0.0589 | 0.3588 | 0.037* | |
| H15B | −0.0337 | 0.2073 | 0.3387 | 0.037* | |
| H15C | 0.0371 | 0.1055 | 0.4111 | 0.037* | |
| S1B | 1.20980 (4) | 0.63000 (4) | 0.11943 (3) | 0.01957 (11) | |
| O1B | 0.72600 (12) | 0.31105 (11) | 0.27336 (9) | 0.0204 (3) | |
| H1O2 | 0.790 (2) | 0.358 (2) | 0.2455 (18) | 0.042 (7)* | |
| N1B | 0.96393 (13) | 0.38885 (13) | 0.14385 (10) | 0.0165 (3) | |
| N2B | 1.07086 (14) | 0.46229 (13) | 0.10739 (11) | 0.0183 (3) | |
| H2N2 | 1.141 (2) | 0.4453 (19) | 0.0585 (17) | 0.035 (6)* | |
| N3B | 0.95163 (13) | 0.58802 (14) | 0.22201 (11) | 0.0191 (3) | |
| H2N3 | 0.8858 (19) | 0.5517 (18) | 0.2277 (14) | 0.023 (5)* | |
| C1B | 0.74994 (15) | 0.22243 (15) | 0.21634 (12) | 0.0160 (3) | |
| C2B | 0.64909 (16) | 0.14034 (16) | 0.24528 (13) | 0.0182 (3) | |
| C3B | 0.67030 (16) | 0.04933 (16) | 0.18792 (13) | 0.0212 (4) | |
| H3BA | 0.6019 | −0.0055 | 0.2052 | 0.025* | |
| C4B | 0.78870 (17) | 0.03605 (16) | 0.10606 (14) | 0.0221 (4) | |
| H4BA | 0.8018 | −0.0285 | 0.0692 | 0.027* | |
| C5B | 0.88741 (16) | 0.11750 (16) | 0.07866 (13) | 0.0198 (3) | |
| H5BA | 0.9683 | 0.1087 | 0.0224 | 0.024* | |
| C6B | 0.87008 (15) | 0.21254 (15) | 0.13242 (12) | 0.0168 (3) | |
| C7B | 0.97581 (16) | 0.29730 (15) | 0.09955 (13) | 0.0178 (3) | |
| H7BA | 1.0559 | 0.2846 | 0.0438 | 0.021* | |
| C8B | 1.06817 (16) | 0.55741 (15) | 0.15303 (12) | 0.0165 (3) | |
| C9B | 0.93058 (15) | 0.68143 (15) | 0.28450 (12) | 0.0171 (3) | |
| H9BA | 0.9867 | 0.7537 | 0.2406 | 0.021* | |
| C10B | 0.97252 (16) | 0.62377 (16) | 0.37971 (13) | 0.0200 (3) | |
| H10C | 1.0684 | 0.5927 | 0.3570 | 0.024* | |
| H10D | 0.9197 | 0.5504 | 0.4230 | 0.024* | |
| C11B | 0.95005 (16) | 0.72239 (16) | 0.44436 (13) | 0.0214 (4) | |
| H11C | 0.9730 | 0.6819 | 0.5077 | 0.026* | |
| H11D | 1.0100 | 0.7914 | 0.4034 | 0.026* | |
| C12B | 0.80487 (16) | 0.77855 (17) | 0.47574 (13) | 0.0219 (4) | |
| H12C | 0.7460 | 0.7118 | 0.5248 | 0.026* | |
| H12D | 0.7953 | 0.8471 | 0.5120 | 0.026* | |
| C13B | 0.76067 (17) | 0.83197 (17) | 0.38142 (14) | 0.0224 (4) | |
| H13C | 0.8111 | 0.9065 | 0.3372 | 0.027* | |
| H13D | 0.6642 | 0.8610 | 0.4051 | 0.027* | |
| C14B | 0.78417 (15) | 0.73274 (16) | 0.31723 (13) | 0.0201 (4) | |
| H14C | 0.7268 | 0.6620 | 0.3590 | 0.024* | |
| H14D | 0.7592 | 0.7717 | 0.2546 | 0.024* | |
| C15B | 0.52399 (16) | 0.15270 (17) | 0.33654 (14) | 0.0237 (4) | |
| H15D | 0.4569 | 0.1011 | 0.3383 | 0.036* | |
| H15E | 0.4886 | 0.2420 | 0.3299 | 0.036* | |
| H15F | 0.5447 | 0.1231 | 0.4010 | 0.036* |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| S1A | 0.01576 (19) | 0.0224 (2) | 0.0179 (2) | −0.00439 (16) | −0.00298 (16) | −0.00655 (17) |
| O1A | 0.0200 (6) | 0.0223 (7) | 0.0185 (6) | −0.0050 (5) | −0.0019 (5) | −0.0086 (5) |
| N1A | 0.0150 (6) | 0.0159 (7) | 0.0166 (7) | −0.0018 (5) | −0.0052 (5) | −0.0041 (5) |
| N2A | 0.0155 (6) | 0.0188 (7) | 0.0155 (7) | −0.0032 (5) | −0.0014 (6) | −0.0072 (6) |
| N3A | 0.0142 (6) | 0.0223 (8) | 0.0187 (7) | −0.0050 (6) | −0.0020 (6) | −0.0095 (6) |
| C1A | 0.0199 (8) | 0.0162 (8) | 0.0153 (8) | −0.0006 (6) | −0.0079 (6) | −0.0036 (6) |
| C2A | 0.0177 (7) | 0.0191 (8) | 0.0173 (8) | −0.0022 (6) | −0.0080 (6) | −0.0012 (7) |
| C3A | 0.0238 (8) | 0.0177 (9) | 0.0244 (9) | −0.0054 (7) | −0.0118 (7) | −0.0013 (7) |
| C4A | 0.0291 (9) | 0.0168 (9) | 0.0238 (9) | −0.0012 (7) | −0.0122 (7) | −0.0070 (7) |
| C5A | 0.0238 (8) | 0.0177 (9) | 0.0187 (9) | 0.0002 (7) | −0.0056 (7) | −0.0061 (7) |
| C6A | 0.0197 (8) | 0.0146 (8) | 0.0151 (8) | −0.0009 (6) | −0.0074 (6) | −0.0025 (6) |
| C7A | 0.0180 (7) | 0.0175 (8) | 0.0146 (8) | −0.0015 (6) | −0.0032 (6) | −0.0043 (6) |
| C8A | 0.0158 (7) | 0.0158 (8) | 0.0153 (8) | −0.0003 (6) | −0.0072 (6) | −0.0024 (6) |
| C9A | 0.0162 (7) | 0.0223 (9) | 0.0159 (8) | −0.0045 (6) | −0.0036 (6) | −0.0081 (7) |
| C10A | 0.0248 (8) | 0.0215 (9) | 0.0225 (9) | −0.0012 (7) | −0.0091 (7) | −0.0072 (7) |
| C11A | 0.0223 (8) | 0.0248 (10) | 0.0327 (10) | 0.0003 (7) | −0.0109 (8) | −0.0142 (8) |
| C12A | 0.0206 (8) | 0.0435 (12) | 0.0320 (11) | −0.0055 (8) | −0.0022 (8) | −0.0262 (9) |
| C13A | 0.0415 (11) | 0.0405 (12) | 0.0187 (10) | −0.0133 (9) | −0.0027 (8) | −0.0120 (8) |
| C14A | 0.0295 (9) | 0.0272 (10) | 0.0180 (9) | −0.0086 (8) | −0.0031 (7) | −0.0066 (7) |
| C15A | 0.0198 (8) | 0.0282 (10) | 0.0244 (9) | −0.0067 (7) | −0.0040 (7) | −0.0056 (8) |
| S1B | 0.01561 (19) | 0.0223 (2) | 0.0206 (2) | −0.00340 (16) | −0.00332 (16) | −0.00756 (17) |
| O1B | 0.0204 (6) | 0.0208 (6) | 0.0198 (6) | −0.0032 (5) | −0.0019 (5) | −0.0106 (5) |
| N1B | 0.0154 (6) | 0.0169 (7) | 0.0173 (7) | −0.0020 (5) | −0.0052 (5) | −0.0042 (6) |
| N2B | 0.0155 (7) | 0.0203 (8) | 0.0177 (7) | −0.0029 (6) | −0.0013 (6) | −0.0074 (6) |
| N3B | 0.0148 (6) | 0.0217 (8) | 0.0227 (8) | −0.0024 (6) | −0.0035 (6) | −0.0117 (6) |
| C1B | 0.0185 (7) | 0.0145 (8) | 0.0151 (8) | 0.0014 (6) | −0.0067 (6) | −0.0039 (6) |
| C2B | 0.0179 (7) | 0.0185 (8) | 0.0176 (8) | −0.0002 (6) | −0.0072 (6) | −0.0022 (7) |
| C3B | 0.0217 (8) | 0.0200 (9) | 0.0244 (9) | −0.0034 (7) | −0.0103 (7) | −0.0047 (7) |
| C4B | 0.0275 (9) | 0.0198 (9) | 0.0246 (9) | −0.0003 (7) | −0.0117 (7) | −0.0109 (7) |
| C5B | 0.0208 (8) | 0.0211 (9) | 0.0176 (8) | 0.0000 (7) | −0.0041 (7) | −0.0095 (7) |
| C6B | 0.0179 (7) | 0.0171 (8) | 0.0163 (8) | −0.0011 (6) | −0.0066 (6) | −0.0042 (6) |
| C7B | 0.0175 (7) | 0.0186 (8) | 0.0158 (8) | 0.0003 (6) | −0.0042 (6) | −0.0049 (7) |
| C8B | 0.0186 (7) | 0.0160 (8) | 0.0142 (8) | −0.0011 (6) | −0.0059 (6) | −0.0021 (6) |
| C9B | 0.0178 (7) | 0.0179 (8) | 0.0167 (8) | −0.0032 (6) | −0.0035 (6) | −0.0079 (7) |
| C10B | 0.0183 (8) | 0.0215 (9) | 0.0199 (9) | 0.0017 (6) | −0.0066 (7) | −0.0063 (7) |
| C11B | 0.0228 (8) | 0.0252 (9) | 0.0188 (9) | −0.0011 (7) | −0.0096 (7) | −0.0063 (7) |
| C12B | 0.0225 (8) | 0.0247 (9) | 0.0196 (9) | −0.0005 (7) | −0.0062 (7) | −0.0092 (7) |
| C13B | 0.0207 (8) | 0.0245 (9) | 0.0262 (10) | 0.0035 (7) | −0.0107 (7) | −0.0121 (8) |
| C14B | 0.0179 (8) | 0.0236 (9) | 0.0218 (9) | −0.0006 (7) | −0.0081 (7) | −0.0087 (7) |
| C15B | 0.0199 (8) | 0.0253 (9) | 0.0231 (9) | −0.0036 (7) | −0.0036 (7) | −0.0048 (7) |
Geometric parameters (Å, º)
| S1A—C8A | 1.6897 (15) | S1B—C8B | 1.6914 (16) |
| O1A—C1A | 1.3583 (19) | O1B—C1B | 1.3569 (19) |
| O1A—H1O1 | 0.80 (2) | O1B—H1O2 | 0.83 (2) |
| N1A—C7A | 1.289 (2) | N1B—C7B | 1.284 (2) |
| N1A—N2A | 1.3758 (18) | N1B—N2B | 1.3762 (18) |
| N2A—C8A | 1.357 (2) | N2B—C8B | 1.357 (2) |
| N2A—H1N2 | 0.85 (2) | N2B—H2N2 | 0.85 (2) |
| N3A—C8A | 1.328 (2) | N3B—C8B | 1.330 (2) |
| N3A—C9A | 1.461 (2) | N3B—C9B | 1.463 (2) |
| N3A—H1N3 | 0.82 (2) | N3B—H2N3 | 0.840 (19) |
| C1A—C6A | 1.404 (2) | C1B—C2B | 1.401 (2) |
| C1A—C2A | 1.406 (2) | C1B—C6B | 1.409 (2) |
| C2A—C3A | 1.390 (2) | C2B—C3B | 1.387 (2) |
| C2A—C15A | 1.499 (2) | C2B—C15B | 1.500 (2) |
| C3A—C4A | 1.390 (2) | C3B—C4B | 1.388 (2) |
| C3A—H3AA | 0.9500 | C3B—H3BA | 0.9500 |
| C4A—C5A | 1.378 (2) | C4B—C5B | 1.382 (2) |
| C4A—H4AA | 0.9500 | C4B—H4BA | 0.9500 |
| C5A—C6A | 1.400 (2) | C5B—C6B | 1.397 (2) |
| C5A—H5AA | 0.9500 | C5B—H5BA | 0.9500 |
| C6A—C7A | 1.458 (2) | C6B—C7B | 1.453 (2) |
| C7A—H7AA | 0.9500 | C7B—H7BA | 0.9500 |
| C9A—C14A | 1.517 (2) | C9B—C14B | 1.522 (2) |
| C9A—C10A | 1.520 (2) | C9B—C10B | 1.526 (2) |
| C9A—H9AA | 1.0000 | C9B—H9BA | 1.0000 |
| C10A—C11A | 1.529 (2) | C10B—C11B | 1.530 (2) |
| C10A—H10A | 0.9900 | C10B—H10C | 0.9900 |
| C10A—H10B | 0.9900 | C10B—H10D | 0.9900 |
| C11A—C12A | 1.519 (3) | C11B—C12B | 1.526 (2) |
| C11A—H11A | 0.9900 | C11B—H11C | 0.9900 |
| C11A—H11B | 0.9900 | C11B—H11D | 0.9900 |
| C12A—C13A | 1.513 (3) | C12B—C13B | 1.523 (2) |
| C12A—H12A | 0.9900 | C12B—H12C | 0.9900 |
| C12A—H12B | 0.9900 | C12B—H12D | 0.9900 |
| C13A—C14A | 1.526 (2) | C13B—C14B | 1.529 (2) |
| C13A—H13A | 0.9900 | C13B—H13C | 0.9900 |
| C13A—H13B | 0.9900 | C13B—H13D | 0.9900 |
| C14A—H14A | 0.9900 | C14B—H14C | 0.9900 |
| C14A—H14B | 0.9900 | C14B—H14D | 0.9900 |
| C15A—H15A | 0.9800 | C15B—H15D | 0.9800 |
| C15A—H15B | 0.9800 | C15B—H15E | 0.9800 |
| C15A—H15C | 0.9800 | C15B—H15F | 0.9800 |
| C1A—O1A—H1O1 | 108.6 (17) | C1B—O1B—H1O2 | 107.4 (15) |
| C7A—N1A—N2A | 116.82 (13) | C7B—N1B—N2B | 116.97 (14) |
| C8A—N2A—N1A | 119.82 (13) | C8B—N2B—N1B | 120.46 (14) |
| C8A—N2A—H1N2 | 120.7 (13) | C8B—N2B—H2N2 | 119.4 (14) |
| N1A—N2A—H1N2 | 117.8 (14) | N1B—N2B—H2N2 | 120.0 (14) |
| C8A—N3A—C9A | 125.71 (13) | C8B—N3B—C9B | 124.99 (13) |
| C8A—N3A—H1N3 | 117.1 (14) | C8B—N3B—H2N3 | 116.0 (13) |
| C9A—N3A—H1N3 | 116.9 (14) | C9B—N3B—H2N3 | 118.9 (13) |
| O1A—C1A—C6A | 122.24 (14) | O1B—C1B—C2B | 116.63 (14) |
| O1A—C1A—C2A | 116.68 (14) | O1B—C1B—C6B | 122.02 (14) |
| C6A—C1A—C2A | 121.08 (15) | C2B—C1B—C6B | 121.35 (15) |
| C3A—C2A—C1A | 117.85 (15) | C3B—C2B—C1B | 117.95 (15) |
| C3A—C2A—C15A | 122.40 (14) | C3B—C2B—C15B | 122.57 (15) |
| C1A—C2A—C15A | 119.74 (15) | C1B—C2B—C15B | 119.48 (15) |
| C4A—C3A—C2A | 122.00 (15) | C2B—C3B—C4B | 121.87 (15) |
| C4A—C3A—H3AA | 119.0 | C2B—C3B—H3BA | 119.1 |
| C2A—C3A—H3AA | 119.0 | C4B—C3B—H3BA | 119.1 |
| C5A—C4A—C3A | 119.37 (16) | C5B—C4B—C3B | 119.48 (15) |
| C5A—C4A—H4AA | 120.3 | C5B—C4B—H4BA | 120.3 |
| C3A—C4A—H4AA | 120.3 | C3B—C4B—H4BA | 120.3 |
| C4A—C5A—C6A | 121.01 (16) | C4B—C5B—C6B | 120.98 (16) |
| C4A—C5A—H5AA | 119.5 | C4B—C5B—H5BA | 119.5 |
| C6A—C5A—H5AA | 119.5 | C6B—C5B—H5BA | 119.5 |
| C5A—C6A—C1A | 118.68 (14) | C5B—C6B—C1B | 118.35 (14) |
| C5A—C6A—C7A | 118.22 (15) | C5B—C6B—C7B | 118.96 (15) |
| C1A—C6A—C7A | 123.09 (14) | C1B—C6B—C7B | 122.70 (14) |
| N1A—C7A—C6A | 121.83 (15) | N1B—C7B—C6B | 121.80 (15) |
| N1A—C7A—H7AA | 119.1 | N1B—C7B—H7BA | 119.1 |
| C6A—C7A—H7AA | 119.1 | C6B—C7B—H7BA | 119.1 |
| N3A—C8A—N2A | 116.73 (14) | N3B—C8B—N2B | 116.78 (14) |
| N3A—C8A—S1A | 123.76 (12) | N3B—C8B—S1B | 124.07 (12) |
| N2A—C8A—S1A | 119.51 (12) | N2B—C8B—S1B | 119.15 (12) |
| N3A—C9A—C14A | 108.61 (13) | N3B—C9B—C14B | 109.69 (12) |
| N3A—C9A—C10A | 112.01 (13) | N3B—C9B—C10B | 111.20 (13) |
| C14A—C9A—C10A | 111.06 (14) | C14B—C9B—C10B | 110.58 (13) |
| N3A—C9A—H9AA | 108.4 | N3B—C9B—H9BA | 108.4 |
| C14A—C9A—H9AA | 108.4 | C14B—C9B—H9BA | 108.4 |
| C10A—C9A—H9AA | 108.4 | C10B—C9B—H9BA | 108.4 |
| C9A—C10A—C11A | 110.55 (14) | C9B—C10B—C11B | 110.68 (13) |
| C9A—C10A—H10A | 109.5 | C9B—C10B—H10C | 109.5 |
| C11A—C10A—H10A | 109.5 | C11B—C10B—H10C | 109.5 |
| C9A—C10A—H10B | 109.5 | C9B—C10B—H10D | 109.5 |
| C11A—C10A—H10B | 109.5 | C11B—C10B—H10D | 109.5 |
| H10A—C10A—H10B | 108.1 | H10C—C10B—H10D | 108.1 |
| C12A—C11A—C10A | 111.31 (14) | C12B—C11B—C10B | 111.23 (13) |
| C12A—C11A—H11A | 109.4 | C12B—C11B—H11C | 109.4 |
| C10A—C11A—H11A | 109.4 | C10B—C11B—H11C | 109.4 |
| C12A—C11A—H11B | 109.4 | C12B—C11B—H11D | 109.4 |
| C10A—C11A—H11B | 109.4 | C10B—C11B—H11D | 109.4 |
| H11A—C11A—H11B | 108.0 | H11C—C11B—H11D | 108.0 |
| C13A—C12A—C11A | 111.40 (15) | C13B—C12B—C11B | 111.49 (14) |
| C13A—C12A—H12A | 109.3 | C13B—C12B—H12C | 109.3 |
| C11A—C12A—H12A | 109.3 | C11B—C12B—H12C | 109.3 |
| C13A—C12A—H12B | 109.3 | C13B—C12B—H12D | 109.3 |
| C11A—C12A—H12B | 109.3 | C11B—C12B—H12D | 109.3 |
| H12A—C12A—H12B | 108.0 | H12C—C12B—H12D | 108.0 |
| C12A—C13A—C14A | 111.91 (16) | C12B—C13B—C14B | 111.59 (14) |
| C12A—C13A—H13A | 109.2 | C12B—C13B—H13C | 109.3 |
| C14A—C13A—H13A | 109.2 | C14B—C13B—H13C | 109.3 |
| C12A—C13A—H13B | 109.2 | C12B—C13B—H13D | 109.3 |
| C14A—C13A—H13B | 109.2 | C14B—C13B—H13D | 109.3 |
| H13A—C13A—H13B | 107.9 | H13C—C13B—H13D | 108.0 |
| C9A—C14A—C13A | 111.02 (14) | C9B—C14B—C13B | 110.42 (13) |
| C9A—C14A—H14A | 109.4 | C9B—C14B—H14C | 109.6 |
| C13A—C14A—H14A | 109.4 | C13B—C14B—H14C | 109.6 |
| C9A—C14A—H14B | 109.4 | C9B—C14B—H14D | 109.6 |
| C13A—C14A—H14B | 109.4 | C13B—C14B—H14D | 109.6 |
| H14A—C14A—H14B | 108.0 | H14C—C14B—H14D | 108.1 |
| C2A—C15A—H15A | 109.5 | C2B—C15B—H15D | 109.5 |
| C2A—C15A—H15B | 109.5 | C2B—C15B—H15E | 109.5 |
| H15A—C15A—H15B | 109.5 | H15D—C15B—H15E | 109.5 |
| C2A—C15A—H15C | 109.5 | C2B—C15B—H15F | 109.5 |
| H15A—C15A—H15C | 109.5 | H15D—C15B—H15F | 109.5 |
| H15B—C15A—H15C | 109.5 | H15E—C15B—H15F | 109.5 |
| C7A—N1A—N2A—C8A | −171.68 (14) | C7B—N1B—N2B—C8B | −177.23 (14) |
| O1A—C1A—C2A—C3A | 179.53 (14) | O1B—C1B—C2B—C3B | 179.53 (14) |
| C6A—C1A—C2A—C3A | −0.3 (2) | C6B—C1B—C2B—C3B | −0.7 (2) |
| O1A—C1A—C2A—C15A | 0.2 (2) | O1B—C1B—C2B—C15B | −1.0 (2) |
| C6A—C1A—C2A—C15A | −179.68 (15) | C6B—C1B—C2B—C15B | 178.77 (15) |
| C1A—C2A—C3A—C4A | 0.3 (2) | C1B—C2B—C3B—C4B | 1.9 (2) |
| C15A—C2A—C3A—C4A | 179.61 (16) | C15B—C2B—C3B—C4B | −177.57 (16) |
| C2A—C3A—C4A—C5A | −0.5 (3) | C2B—C3B—C4B—C5B | −1.7 (3) |
| C3A—C4A—C5A—C6A | 0.8 (3) | C3B—C4B—C5B—C6B | 0.3 (3) |
| C4A—C5A—C6A—C1A | −0.9 (2) | C4B—C5B—C6B—C1B | 0.8 (2) |
| C4A—C5A—C6A—C7A | 178.73 (15) | C4B—C5B—C6B—C7B | −178.94 (15) |
| O1A—C1A—C6A—C5A | −179.23 (14) | O1B—C1B—C6B—C5B | 179.16 (14) |
| C2A—C1A—C6A—C5A | 0.6 (2) | C2B—C1B—C6B—C5B | −0.6 (2) |
| O1A—C1A—C6A—C7A | 1.2 (2) | O1B—C1B—C6B—C7B | −1.1 (2) |
| C2A—C1A—C6A—C7A | −178.96 (14) | C2B—C1B—C6B—C7B | 179.12 (15) |
| N2A—N1A—C7A—C6A | 178.28 (13) | N2B—N1B—C7B—C6B | 179.20 (14) |
| C5A—C6A—C7A—N1A | −176.61 (15) | C5B—C6B—C7B—N1B | 177.83 (15) |
| C1A—C6A—C7A—N1A | 3.0 (2) | C1B—C6B—C7B—N1B | −1.9 (2) |
| C9A—N3A—C8A—N2A | 178.07 (14) | C9B—N3B—C8B—N2B | 175.59 (14) |
| C9A—N3A—C8A—S1A | −2.3 (2) | C9B—N3B—C8B—S1B | −4.8 (2) |
| N1A—N2A—C8A—N3A | −7.4 (2) | N1B—N2B—C8B—N3B | −10.2 (2) |
| N1A—N2A—C8A—S1A | 172.92 (11) | N1B—N2B—C8B—S1B | 170.21 (11) |
| C8A—N3A—C9A—C14A | −151.70 (16) | C8B—N3B—C9B—C14B | 155.77 (15) |
| C8A—N3A—C9A—C10A | 85.26 (19) | C8B—N3B—C9B—C10B | −81.60 (19) |
| N3A—C9A—C10A—C11A | 178.51 (13) | N3B—C9B—C10B—C11B | 179.99 (13) |
| C14A—C9A—C10A—C11A | 56.87 (18) | C14B—C9B—C10B—C11B | −57.90 (17) |
| C9A—C10A—C11A—C12A | −56.18 (19) | C9B—C10B—C11B—C12B | 55.88 (18) |
| C10A—C11A—C12A—C13A | 54.83 (19) | C10B—C11B—C12B—C13B | −54.08 (19) |
| C11A—C12A—C13A—C14A | −54.1 (2) | C11B—C12B—C13B—C14B | 54.32 (19) |
| N3A—C9A—C14A—C13A | −179.67 (15) | N3B—C9B—C14B—C13B | −179.21 (14) |
| C10A—C9A—C14A—C13A | −56.06 (19) | C10B—C9B—C14B—C13B | 57.79 (18) |
| C12A—C13A—C14A—C9A | 54.7 (2) | C12B—C13B—C14B—C9B | −56.10 (19) |
Hydrogen-bond geometry (Å, º)
Cg1 is the centroid of benzene ring C1A–C6A.
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1A—H1O1···N1A | 0.80 (2) | 1.98 (2) | 2.6844 (19) | 146 (2) |
| O1B—H1O2···N1B | 0.84 (2) | 1.91 (2) | 2.664 (2) | 148 (2) |
| N2A—H1N2···S1Bi | 0.85 (2) | 2.60 (2) | 3.4414 (16) | 170 (2) |
| N2B—H2N2···S1Ai | 0.85 (2) | 2.53 (2) | 3.3568 (15) | 164 (2) |
| C11A—H11B···Cg1ii | 0.99 | 2.93 | 3.801 (2) | 148 |
Symmetry codes: (i) −x+2, −y+1, −z; (ii) x, y+1, z.
Funding Statement
This work was funded by Universiti Sains Malaysia grant 1001/PKIMIA/811269. The World Academy of Sciences grant . Shahjalal University of Science and Technology grant PS/2018/1/04, 2018–2019 to Md. A. Arafath. Malaysian Government grant MyBrain15 to H. C. Kwong.
References
- Alomar, K., Khan, M. A., Allain, M. & Bouet, G. (2009). Polyhedron, 28, 1273–1280.
- Arafath, M. A., Adam, F. & Razali, M. R. (2017a). IUCrData, 2, x161997.
- Arafath, M. A., Adam, F., Razali, M. R., Hassan, L. E. A., Ahamed, M. B. K. & Majid, A. M. S. (2017b). J. Mol. Struct. 1130, 791–798.
- Arafath, M. A., Kwong, H. C., Adam, F. & Razali, M. R. (2018). Acta Cryst. E74, 1460–1462. [DOI] [PMC free article] [PubMed]
- Arion, V., Revenco, M., Gradinaru, J., Simonov, Y., Kravtsov, V., Gerbeleu, N., Saint-Aman, E. & Adams, F. (2001). Rev. Inorg. Chem. 21, 1–42.
- Basheer, S. M., Bhuvanesh, N. S. P. & Sreekanth, A. (2016a). J. Fluor. Chem. 191, 129–142.
- Basheer, S. M., Willis, A. C., Pace, R. J. & Sreekanth, A. (2016b). Polyhedron, 109, 7–18.
- Basheer, S. M., Willis, A. C. & Sreekanth, A. (2017). J. Lumin. 183, 266–280.
- Bhat, M. A., Al-Dhfyan, A., Khan, A. A., Al-Harbi, N., Manogaran, P. S., Alanazi, A. M., Fun, H.-K. & Al-Omar, M. A. (2015). Bioorg. Med. Chem. Lett. 25, 83–87. [DOI] [PubMed]
- Bruker (2012). Bruker AXS Inc., Madison. Wisconsin, USA.
- Chandra, S. & Sangeetika, X. (2004). Spectrochim. Acta A, 60, 147–153. [DOI] [PubMed]
- Gerbeleu, N. V., Arion, V. B. & Burgess, J. P. (2008). Template Synthesis of Macrocyclic Compounds. John Wiley & Sons.
- Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. [DOI] [PMC free article] [PubMed]
- Jacob, J. M. & Kurup, M. R. P. (2012). Acta Cryst. E68, o836–o837. [DOI] [PMC free article] [PubMed]
- Koo, C. H., Kim, C. H. & Park, Y. J. (1981). J. Korean Chem. Soc. 25, 343–350.
- Leovac, V. & Češljević, V. (2002). Coordination Chemistry of Isothiosemicarbazide and Its Derivatives. Faculty of Science, University of Novi Sad, Serbia.
- Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470.
- Mohamed, G. G., Omar, M. & Ibrahim, A. A. (2009). Eur. J. Med. Chem. 44, 4801–4812. [DOI] [PubMed]
- Padhyé, S. & Kauffman, G. B. (1985). Coord. Chem. Rev. 63, 127–160.
- Rayati, S., Sadeghzadeh, N. & Khavasi, H. R. (2007). Inorg. Chem. Commun. 10, 1545–1548.
- Salam, M., Affan, M., Ahmad, F. B. & Arafath, M. A. (2012a). J. Coord. Chem. 65, 1999–2007.
- Salam, M., Affan, M., Ahmad, F. B., Arafath, M. A., Tahir, M. I. M. & Shamsuddin, M. B. (2012b). J. Coord. Chem. 65, 3174–3187.
- Seena, E. B., Bessy Raj, B. N., Prathapachandra Kurup, M. R. & Suresh, E. (2006). J. Chem. Crystallogr. 36, 189–193.
- Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
- Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8.
- Siddiki, A. N. A., Rahman, M. S., Rahman, M. A., Salam, M. A., Yousuf, M. A., Islam, M. F. & Arafat, M. A. (2012). Bangladesh Pharmaceutical Journal, 15, 83–87.
- Singh, N. K., Srivastava, A., Sodhi, A. & Ranjan, P. (2000). Transit. Met. Chem. 25, 133–140.
- Spek, A. L. (2009). Acta Cryst. D65, 148–155. [DOI] [PMC free article] [PubMed]
- Vieites, M., Otero, L., Santos, D., Olea-Azar, C., Norambuena, E., Aguirre, G., Cerecetto, H., González, M., Kemmerling, U., Morello, A., Diego Maya, J. & Gambino, D. (2009). J. Inorg. Biochem. 103, 411–418. [DOI] [PubMed]
- Ziessel, R. (2001). Coord. Chem. Rev. 216–217, 195–223.
Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) I, Global. DOI: 10.1107/S2056989019008946/su5501sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989019008946/su5501Isup2.hkl
CCDC reference: 1480651
Additional supporting information: crystallographic information; 3D view; checkCIF report