fac-Tri­aqua­(1,10-phenanthroline-κ2N,N′)(sulfato-κO)cobalt(II): crystal structure, Hirshfeld surface analysis and computational study

Setifi, Z.; Kwong, H.C.; Tiekink, E.R.T.; Maris, T.; Setifi, F.

doi:10.1107/S2056989020006271

research communications

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ISSN: 2056-9890

Volume 76| Part 6| June 2020| Pages 835-840

https://doi.org/10.1107/S2056989020006271

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fac-Triaqua(1,10-phenanthroline-κ²N,N′)(sulfato-κO)cobalt(II): crystal structure, Hirshfeld surface analysis and computational study

Zouaoui Setifi,^a,^b ‡ Huey Chong Kwong,^c Edward R. T. Tiekink,^c ^* Thierry Maris ^d and Fatima Setifi ^b

^aDépartement de Technologie, Faculté de Technologie, Université 20 Août 1955-Skikda, BP 26, Route d'El-Hadaiek, Skikda 21000, Algeria, ^bLaboratoire de Chimie, Ingénierie Moléculaire et Nanostructures (LCIMN), Université Ferhat Abbas Sétif 1, Sétif 19000, Algeria, ^cResearch Centre for Crystalline Materials, School of Science and Technology, Sunway University, 47500 Bandar Sunway, Selangor Darul Ehsan, Malaysia, and ^dDepartment of Chemistry, Université de Montréal, 2900 Edouard-Montpetit Blvd, Montreal, Quebec, H3T1J4, Canada
^*Correspondence e-mail: edwardt@sunway.edu.my

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 6 May 2020; accepted 8 May 2020; online 15 May 2020)

The Co^II atom in the title complex, [Co(SO₄)(C₁₂H₈N₂)(H₂O)₃] (or C₁₂H₁₄CoN₂O₇S), is octahedrally coordinated within a cis-N₂O₄ donor set defined by the chelating N-donors of the 1,10-phenanthroline ligand, sulfate-O and three aqua-O atoms, the latter occupying an octahedral face. In the crystal, supramolecular layers lying parallel to (110) are sustained by aqua-O—H⋯O(sulfate) hydrogen bonding. The layers stack along the c-axis direction with the closest directional interaction between them being a weak phenanthroline-C—H⋯O(sulfate) contact. There are four significant types of contact contributing to the calculated Hirshfeld surface: at 44.5%, the major contribution comes from O—H⋯O contacts followed by H⋯H (28.6%), H⋯C/C⋯H (19.5%) and C⋯C (5.7%) contacts. The dominance of the electrostatic potential force in the molecular packing is also evident in the calculated energy frameworks. The title complex is isostructural with its manganese, zinc and cadmium containing analogues and isomeric with its mer-triaqua analogue.

Keywords: crystal structure; cobalt(II); hydrogen bonding; Hirshfeld surface analysis.

CCDC reference: 2002737

1. Chemical context

As a consequence of their ability to link metal ions in a variety of different ways, polynitrile anions, either functioning alone or in combination with neutral co-ligands, provide opportunities for the generation of molecular architectures with varying dimensions and topologies (Benmansour et al., 2012 ). The presence of other potential donor groups such as those derived from –OH, –SH or –NH₂, together with their rigidity and electronic delocalization, mean that polynitrile anions can also lead to new magnetic and luminescent coordination polymers based on transition-metal ions (Benmansour et al., 2010 ; Kayukov et al., 2017 ; Lehchili et al., 2017 ; Setifi et al., 2017 ). Furthermore, the use of polynitrile anions for the synthesis of interesting discrete and polymeric bistable materials has been described (Setifi et al., 2014 ; Milin et al., 2016 ; Pittala et al., 2017 ). In view of this coordinating ability, these ligands have also been explored for their utility in developing materials capable of magnetic exchange coupling (Addala et al., 2015 ; Déniel et al., 2017 ). It was during the course of attempts to prepare such complexes with 1,10-phenanthroline as a co-ligand that the title complex, (I), was unexpectedly obtained. Herein, the crystal and molecular structures of (I) are described, a study complemented by an analysis of the molecular packing by calculating the Hirshfeld surfaces as well as a computational chemistry study.

2. Structural commentary

The molecule of (I) is shown in Fig. 1 and selected geometric parameters are collated in Table 1. The Co^II complex features a chelating 1,10-phenanthroline ligand, a monodentate sulfate di-anion and three coordinated water molecules. The resulting N₂O₄ donor set defines a distorted octahedral coordination geometry for the Co^II atom, with the water molecules occupying one octahedral face. The greatest deviations from a regular geometry is seen in the restricted bite angle subtended by the 1,10-phenanthroline ligand, i.e. N1—Co1—N2 = 78.21 (6)°, and in the trans O2W—Co—N2 angle of 166.55 (6)°. The Co—N bond lengths are equal within experimental error but the Co—O(aqua) bonds span an experimentally distinct range, Table 1. The observation that the shortest and longest Co—O(aqua) bonds have each aqua-O atom trans to a nitrogen atom suggests the differences in bond lengths are due to the considerable hydrogen bonding operating in the crystal. Indeed, there is an intramolecular aqua-O1W—H⋯O3(sulfate) hydrogen bond, Table 2. The coordinated sulfate-O1 atom forms the longer of the four sulfate-S—O bonds, Table 1. The S—O bond lengths formed by the non-coordinating sulfate-oxygen atoms spans an experimentally distinct range of 1.4616 (14) Å for S1—O2, to 1.4813 (14) Å for S1—O3. As discussed below, the sulfate-O1–O4 oxygen atoms form, respectively, one, one, two and two hydrogen bonds with the water molecules, which is consistent with the S1—O2 bond length being the shortest of the four bonds. The above notwithstanding, it is likely that the formal negative charge on the SO₃ residue is delocalized over the three non-coordinating S—O bonds.

Table 1
Selected bond lengths (Å)

Co—O1	2.1386 (13)	Co—N2	2.1453 (16)
Co—O1W	2.1110 (14)	S1—O1	1.4997 (13)
Co—O2W	2.0782 (15)	S1—O2	1.4616 (14)
Co—O3W	2.1024 (14)	S1—O3	1.4813 (14)
Co—N1	2.1356 (15)	S1—O4	1.4784 (14)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W⋯O3	0.84 (2)	1.89 (2)	2.680 (2)	158 (2)
O1W—H2W⋯O1ⁱ	0.83 (1)	1.95 (1)	2.7818 (19)	172 (2)
O2W—H3W⋯O3ⁱⁱ	0.84 (2)	1.91 (2)	2.744 (2)	175 (3)
O2W—H4W⋯O4ⁱⁱⁱ	0.85 (1)	1.93 (1)	2.770 (2)	167 (3)
O3W—H5W⋯O4ⁱ	0.82 (2)	1.95 (2)	2.7548 (19)	168 (3)
O3W—H6W⋯O2ⁱⁱⁱ	0.82 (2)	1.84 (2)	2.6560 (19)	178 (3)
C3—H3⋯O2^iv	0.95	2.45	3.252 (3)	142
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) x+1, y, z; (iv) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ .

Figure 1
The molecular structure of (I)

showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.

3. Supramolecular features

Each of the aqua ligands donates two hydrogen bonds to different sulfate-O atoms, one of these hydrogen bonds is intramolecular while the remaining are intermolecular, Table 2. The result of the hydrogen bonding is the formation of a supramolecular layer lying parallel to (110). A simplified view of the hydrogen bonding scheme is shown in Fig. 2(a). The aqua molecule forming the intramolecular O1W—H⋯O3 hydrogen bond forms a second hydrogen bond to the coordinated O1 atom of a symmetry-related molecule, and the O2W aqua ligand of this molecule connects to the O3 atom of the original molecule, leading to the formation of a non-symmetric eight-membered {⋯HOH⋯O⋯HOCoO} synthon. The second hydrogen atom of the O2W ligand forms a connection to a sulfate-O4 atom, which is also hydrogen bonded to an O3W molecule, which forms an additional link to a symmetry related sulfate-O2 atom with the result a {⋯HOH⋯OSO⋯HOH⋯O} non-symmetric ten-membered synthon is formed. Two additional eight-membered synthons, {HOCoOH⋯OSO}, are formed as a result of the hydrogen-bonding scheme as adjacent pairs of aqua molecules effectively bridge two sulfoxide residues. As seen from Fig. 2(b), the 1,10-phenanthroline molecules project to either side of the supramolecular layer. The layers inter-digitate along [001], Fig. 2(c), with the closest connections between layers being phenanthroline-C—H⋯O2(sulfate) interactions, Table 2. A deeper analysis of the molecular packing is found in the next two sections of this paper.

Figure 2
Molecular packing in the crystal of (I)

: (a) supramolecular layer sustained by aqua-O—H⋯O(sulfate) hydrogen bonding shown as orange dashed lines, only the five-membered chelate rings are shown for reasons of clarity, (b) a side-on view of the layer shown in (a) and (c) a view of the unit-cell contents down the b axis showing the stacking of layers along the c-axis direction, with the phenanthroline-C—H⋯O(sulfate) interactions between layers shown as blue dashed lines.

4. Hirshfeld surface analysis

In order to understand further the interactions operating in the crystal of (I), the Hirshfeld surfaces and two-dimensional fingerprint plots were calculated employing the program Crystal Explorer 17 (Turner et al., 2017 ) and literature procedures (Tan et al., 2019 ). The intermolecular O—H⋯O hydrogen bonds in (I), Table 2, are characterized as pairs of bright-red spots near the aqua-O and sulfate-O atoms on the Hirshfeld surface mapped over d_norm shown in Fig. 3. The faint-red spots near the phenanthroline-C—H (H1, H3 H6 and H10) atoms on the d_norm-mapped Hirshfeld surface in the two views of Fig. 4 represent the influence of the weak C3—H3⋯O2 and C10—H10⋯O1 interactions as well as H1⋯O3, H6⋯O3W short contacts, Table 3. The donors and acceptors of the weak C—H⋯O interaction are viewed as blue and red regions on the Hirshfeld surface mapped over the calculated electrostatic potential in Fig. 5, and which correspond to positive and negative electrostatic potentials.

Table 3
A summary of short interatomic contacts (Å) in (I)^a

Contact	Distance	Symmetry operation
H2W⋯O1^b	1.81	−x + 1, y − $[{1\over 2}]$ , −z + $[{1\over 2}]$
H3W⋯O3^b	1.76	−x + 1, y + $[{1\over 2}]$ , −z + $[{1\over 2}]$
H4W⋯O4^b	1.81	x + 1, y, z
H5W⋯O4^b	1.79	−x + 1, y − $[{1\over 2}]$ , −z + $[{1\over 2}]$
H6W⋯O2^b	1.67	x + 1, y, z
H1⋯O3	2.33	−x + 1, y + $[{1\over 2}]$ , −z + $[{1\over 2}]$
H3⋯O2	2.35	x + $[{1\over 2}]$ , −y + $[{3\over 2}]$ , − z + 1
H6⋯O3W	2.51	x − $[{1\over 2}]$ , −y + $[{1\over 2}]$ , − z + 1
H10⋯O1	2.40	−x + 1, y − $[{1\over 2}]$ , − z + $[{1\over 2}]$
Notes: (a) The interatomic distances are calculated in Crystal Explorer 17 (Turner et al., 2017) whereby the X—H bond lengths are adjusted to their neutron values; (b) these interactions correspond to conventional hydrogen bonds.

Figure 3
A view of the Hirshfeld surface mapped over d_norm for (I)

in the range of −0.729 to +1.105 arbitrary units, highlighting O—H⋯O interactions.

Figure 4
Two views of the Hirshfeld surface mapped over d_norm for (I)

in the range of −0.729 to +1.105 arbitrary units, highlighting weak C—H⋯O interactions and short contacts.

Figure 5
A view of the Hirshfeld surface mapped over the calculated electrostatic potential for (I)

. The potentials were calculated using the STO-3G basis set at Hartree–Fock level of theory over a range of −4.381 to 4.109 atomic units. The red and blue regions represent negative and positive electrostatic potentials, respectively.

The overall two-dimensional fingerprint plot of (I) is shown in Fig. 6(a). The overall contacts are also delineated into H⋯H, H⋯O/O⋯H, H⋯C/C⋯H and C⋯C contacts, as displayed in Fig. 6(b)–(e), respectively. The short interatomic H⋯H contacts are characterized as the pair of beak-shaped tips at d_e + d_i ∼2.3 Å, Fig. 6(b), and contribute 28.6% to the overall surface contacts. The significant O—H⋯O contacts between the aqua- and sulfate-O atoms make the major contribution to the overall contacts (44.5%), and these are represented as pairs of well-defined spikes at d_e + d_i ∼1.7 Å in Fig. 6(c). The short interatomic H⋯C/C⋯H (19.5%) and C⋯C (5.7%) contacts are, respectively, characterized as pairs of broad symmetrical wings at d_e + d_i ∼2.9 Å in Fig. 6(d), and the vase-shaped distribution of points at d_e + d_i ∼3.5 Å in Fig. 6(e). The accumulated contribution of the remaining interatomic contacts is less than 2% and has a negligible effect on the packing.

Figure 6
(a) The overall two-dimensional fingerprint plots for (I)

, and those delineated into (b) H⋯H, (c) O⋯H/H⋯O, (d) C⋯H/H⋯C and (e) C⋯C contacts.

5. Computational chemistry

In the present analysis, the pairwise interaction energies between the molecules in the crystal were calculated by summing up four different energy components, i.e. the electrostatic (E_ele), polarization (E_pol), dispersion (E_dis) and exchange-repulsion (E_rep) energy terms, after Turner et al. (2017). These energies were obtained by applying the wave functions calculated at the B3LYP/6-31G(d,p) level of theory. The benchmarked energies were scaled according to Mackenzie et al. (2017 ) while E_ele, E_pol, E_dis and E_rep were scaled as 1.057, 0.740, 0.871 and 0.618, respectively (Edwards et al., 2017 ). The intermolecular interaction energies are collated in Table 4. Consistent with the presence of strong O—H⋯O hydrogen-bonding interactions in the crystal, the electrostatic energy component has a major influence in the formation of supramolecular architecture of (I), Table 4. The energy associated with the C—H⋯O interactions involving the sulfate-O atoms (−66.8 and −55.7 kJ mol⁻¹) are greater than for the C—H⋯O interaction involving the aqua-O atoms (−30.6 kJ mol⁻¹). The energy frameworks were also computed and illustrate the above conclusions, Fig. 7. These clearly demonstrate the dominance of the electrostatic potential energy in the molecular packing.

Table 4
A summary of interaction energies (kJ mol⁻¹) calculated for (I)

Contact	R (Å)	E_ele	E_pol	E_dis	E_rep	E_tot
O1W—H2W⋯O1ⁱ +	6.78	−330.8	−116.8	−49.6	180.1	−368.1
O3W—H5W⋯O4ⁱ +
O2W—H3W⋯O3ⁱⁱ +
C10—H10⋯O1ⁱ
O3W—H6W⋯O2ⁱⁱⁱ +	7.97	−198.3	−63.8	−16.4	121.0	−196.4
O2W—H4W⋯O4ⁱⁱⁱ
C5—H5⋯O3^v +	10.47	−46.2	−19.3	−9.8	7.8	−66.8
C6—H6⋯O4^v
C3—H3⋯O2^iv	7.64	−17.3	−30.2	−42.3	35.3	−55.7
C6—H6⋯O3W^vi	8.03	−2.3	−13.7	−37.7	24.0	−30.6
Symmetry operations: (i) −x + 1, y − $[{1\over 2}]$ , −z + $[{1\over 2}]$ ; (ii) − x + 1, y + $[{1\over 2}]$ , − z + $[{1\over 2}]$ ; (iii) x + 1, y, z; (iv) x + $[{1\over 2}]$ , −y + $[{3\over 2}]$ , −z + 1; (v) −x + $[{1\over 2}]$ , − y + 1, z + $[{1\over 2}]$ ; (vi) x – 1/2, −y + $[{1\over 2}]$ , −z + 1.

Figure 7
Perspective views of the energy frameworks calculated for (I)

, showing the (a) electrostatic potential force, (b) dispersion force and (c) total energy, each plotted down the b axis. The radii of the cylinders are proportional to the relative magnitudes of the corresponding energies and were adjusted to the same scale factor of 20 with a cut-off value of 5 kJ mol⁻¹ within 2 × 2 × 2 unit cells.

6. Database survey

There are several literature analogues of (I), i.e. molecules conforming to the general formula fac-M(1,10-phenanthroline)(OH₂)₃OSO₃. These include M = Mn (XATNAH; Zheng et al., 2000 ), M = Zn (IJOQAA; Liu et al., 2011 ) and M = Cd (RACWUO; Li et al., 2003 ). The three literature structures are isostructural with (I). Literature analogues are also available for the isomeric mer-M(1,10-phenanthroline)(OH₂)₃OSO₃ species, i.e. M = Mn (UGOJUV; Zheng et al., 2002 ), M = Fe (MIKJAS; Li et al., 2007 ), M = Co (FICNOU; Li & Zhou, 1987 ) and M = Ni (ESUZOH; He et al., 2003 ). The four mer-isomers are also isostructural, crystallizing in the monoclinic space group P2₁/c. There are two pairs of structures (containing Mn and Co) crystallizing in both forms. For the Mn complexes, the authors reporting the structure of the mer-isomer indicated that both forms were formed concomitantly from the slow evaporation of a methanol solution of the complex (Zheng et al., 2002). To a first approximation, the molecular packing in the mer form resembles that for the fac-isomer in that supramolecular layers are formed by hydrogen bonding whereby each aqua ligand hydrogen bonds to two different sulfate-O atoms, i.e. as for (I).

The key difference in the packing between the two isomers arises as one sulfate-O atom in the mer-isomer participates in three hydrogen bonds at the expense of the hydrogen bond involving the coordinated sulfate-O1 atom. The presence of inter-layer phenanthroline-C—H⋯O(sulfate) interactions persist as for the fac-isomer with the crucial difference that π–π stacking interactions are evident in the inter-layer region of the mer-form with the shortest separation being 3.76 Å.

The different packing arrangements result in different densities with that for (I) of 1.776 g cm⁻³ being greater than 1.723 g cm⁻³ for the mer-isomer (FICNOU; Li & Zhou, 1987). The calculated packing efficiencies follow this trend being 72.8 and 66.5%, respectively. Similar results are noted for the pair of Mn structures, i.e. 1.690 g cm⁻³ and 71.1% for the fac-isomer (Zheng et al., 2000) c.f. 1.643 g cm⁻³ and 68.7% for the mer-isomer (Zheng et al., 2000). The consistency of these parameters may suggest that the fac-isomer in these M(1,10-phenanthroline)(OH₂)₃OSO₃ complexes is the thermodynamically more stable form.

Given the isostructural relationship in the series (I), IJOQAA, RACWUO and XATNAH, it was thought of interest to compare the percentage contributions of the difference intermolecular contacts to the calculated Hirshfeld surfaces. Thus, these were calculated for the three literature structures as were the overall and delineated two-dimensional fingerprint plots. Qualitatively, the fingerprint plots had the same general appearance in accord with expectation (Jotani et al., 2019 ). The calculated percentage contributions to the Hirshfeld surfaces for the four complexes are collated in Table 5. Clearly and as would be expected, the data in Table 5 reveal a high degree of concordance in the percentage contributions to the Hirshfeld surfaces between the four isostructural complexes.

Table 5
Percentage contributions to intermolecular contacts on the Hirshfeld surface calculated for (I)

Contact		Percentage contribution
	(I), M = Co	IJOQAA, M = Zn	RACWUO, M = Cd	XATNAH, M = Mn
H⋯H	28.6	30.1	27.6	27.2
H⋯O/O⋯H	44.5	43.3	45.8	45.9
H⋯C/C⋯H	19.5	19.1	19.2	19.1
C⋯C	5.7	5.7	5.2	5.6
Others	1.7	1.8	2.2	2.2

7. Synthesis and crystallization

The title compound was synthesized solvothermally under autogenous pressure from a mixture of CoSO₄·7H₂O (28 mg, 0.1 mmol), 1,10-phenanthroline (18 mg, 0.1 mmol) and K(tcnoet) (45 mg, 0.2 mmol) in water–methanol (4:1v/v, 25 ml); where tcnoet is 1,1,3,3-tetracyano-2-ethoxypropenide. The mixture was sealed in a Teflon-lined autoclave and held at 403 K for 2 days, and then cooled to room temperature at a rate of 10 K h⁻¹; yield: 35%. Light-pink blocks of the title complex suitable for single-crystal X-ray diffraction were selected directly from the synthesized product.

8. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 6. The carbon-bound H atoms were placed in calculated positions (C—H = 0.95 Å) and were included in the refinement in the riding-model approximation, with U_iso(H) set to 1.2U_eq(C). The oxygen-bound H atoms were located from a difference-Fourier map and refined with O—H = 0.84±0.01 Å, and with U_iso(H) set to 1.5U_eq(O). Owing to poor agreement, four reflections, i.e. (0 1 4), (0 0 2), (0 1 2) and (0 0 4), were omitted from the final cycles of refinement. The absolute structure was determined based on differences in Friedel pairs included in the data set.

Table 6
Experimental details

Crystal data
Chemical formula	[Co(SO₄)(C₁₂H₈N₂)(H₂O)₃]
M_r	389.24
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	150
a, b, c (Å)	7.9732 (4), 9.5589 (4), 19.0955 (9)
V (Å³)	1455.36 (12)
Z	4
Radiation type	Ga Kα, λ = 1.34139 Å
μ (mm⁻¹)	7.61
Crystal size (mm)	0.08 × 0.08 × 0.05

Data collection
Diffractometer	Bruker Venture Metaljet
Absorption correction	Multi-scan (SADABS; Bruker, 2016 )
T_min, T_max	0.064, 0.155
No. of measured, independent and observed [I > 2σ(I)] reflections	25223, 3202, 3126
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.017, 0.046, 0.99
No. of reflections	3202
No. of parameters	227
No. of restraints	6
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.58
Absolute structure	Flack x determined using 1194 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 ).
Absolute structure parameter	0.0101 (17)
Computer programs: APEX2 and SAINT (Bruker, 2013 ), SHELXS (Sheldrick, 2015a ), SHELXL2018/3 (Sheldrick, 2015b ), ORTEP-3 for Windows (Farrugia, 2012 ), DIAMOND (Brandenburg, 2006 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 2002737

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2056989020006271/hb7911sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989020006271/hb7911Isup2.hkl

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012), DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

fac-Triaqua(1,10-phenanthroline-κ²N,N')(sulfato-κO)cobalt(II) top

Crystal data top

[Co(SO₄)(C₁₂H₈N₂)(H₂O)₃]	D_x = 1.776 Mg m⁻³
M_r = 389.24	Ga Kα radiation, λ = 1.34139 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 9840 reflections
a = 7.9732 (4) Å	θ = 4.0–60.7°
b = 9.5589 (4) Å	µ = 7.61 mm⁻¹
c = 19.0955 (9) Å	T = 150 K
V = 1455.36 (12) Å³	Prism, light-pink
Z = 4	0.08 × 0.08 × 0.05 mm
F(000) = 796

Data collection top

Bruker Venture Metaljet diffractometer	3202 independent reflections
Radiation source: Metal Jet, Gallium Liquid Metal Jet Source	3126 reflections with I > 2σ(I)
Helios MX Mirror Optics monochromator	R_int = 0.033
Detector resolution: 10.24 pixels mm^-1	θ_max = 60.6°, θ_min = 4.5°
ω and φ scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −12→12
T_min = 0.064, T_max = 0.155	l = −24→24
25223 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.017	w = 1/[σ²(F_o²) + (0.0202P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.046	(Δ/σ)_max = 0.001
S = 0.99	Δρ_max = 0.51 e Å⁻³
3202 reflections	Δρ_min = −0.58 e Å⁻³
227 parameters	Extinction correction: SHELXL-2018/3 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
6 restraints	Extinction coefficient: 0.0057 (5)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack x determined using 1194 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013).
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.0101 (17)

Special details top

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) top

	x	y	z	U_iso*/U_eq
Co	0.63811 (3)	0.53373 (3)	0.31720 (2)	0.02111 (9)
S1	0.24258 (5)	0.56910 (4)	0.27630 (2)	0.02212 (11)
O1	0.40704 (16)	0.63702 (14)	0.29351 (7)	0.0239 (3)
O2	0.17822 (17)	0.49545 (15)	0.33775 (7)	0.0291 (3)
O3	0.26932 (17)	0.46986 (15)	0.21777 (7)	0.0289 (3)
O4	0.12543 (18)	0.68089 (14)	0.25463 (7)	0.0290 (3)
O1W	0.60122 (18)	0.42633 (14)	0.22184 (7)	0.0267 (3)
H1W	0.5005 (18)	0.431 (3)	0.2097 (13)	0.040*
H2W	0.607 (3)	0.3405 (14)	0.2144 (14)	0.040*
O2W	0.77952 (18)	0.68717 (15)	0.26762 (8)	0.0296 (3)
H3W	0.768 (4)	0.7735 (15)	0.2743 (14)	0.044*
H4W	0.8839 (17)	0.673 (3)	0.2607 (15)	0.044*
O3W	0.85965 (17)	0.41650 (15)	0.32821 (7)	0.0281 (3)
H5W	0.874 (4)	0.353 (2)	0.2999 (12)	0.042*
H6W	0.9583 (19)	0.440 (3)	0.3324 (14)	0.042*
N1	0.6414 (2)	0.64091 (16)	0.41532 (8)	0.0252 (3)
N2	0.5377 (2)	0.37822 (16)	0.38651 (8)	0.0240 (3)
C1	0.6826 (3)	0.7733 (2)	0.42840 (11)	0.0307 (4)
H1	0.716162	0.831005	0.390391	0.037*
C2	0.6788 (3)	0.8312 (2)	0.49569 (12)	0.0349 (5)
H2	0.706310	0.926898	0.502638	0.042*
C3	0.6351 (3)	0.7487 (2)	0.55149 (12)	0.0357 (5)
H3	0.634774	0.786001	0.597609	0.043*
C4	0.5906 (3)	0.6081 (2)	0.53970 (11)	0.0311 (4)
C5	0.5383 (3)	0.5154 (3)	0.59456 (11)	0.0374 (5)
H5	0.537335	0.547683	0.641615	0.045*
C6	0.4904 (3)	0.3828 (3)	0.58034 (11)	0.0394 (5)
H6	0.456658	0.323326	0.617613	0.047*
C7	0.4897 (3)	0.3302 (2)	0.50992 (11)	0.0315 (4)
C8	0.4422 (3)	0.1926 (2)	0.49259 (12)	0.0358 (5)
H8	0.410012	0.128509	0.528178	0.043*
C9	0.4430 (3)	0.1523 (2)	0.42371 (12)	0.0350 (5)
H9	0.411464	0.059775	0.411121	0.042*
C10	0.4904 (3)	0.2480 (2)	0.37212 (11)	0.0290 (4)
H10	0.488688	0.218795	0.324580	0.035*
C11	0.5388 (2)	0.4191 (2)	0.45479 (10)	0.0251 (4)
C12	0.5919 (2)	0.5600 (2)	0.46986 (10)	0.0258 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co	0.02084 (13)	0.02088 (13)	0.02160 (13)	−0.00016 (10)	0.00033 (10)	0.00127 (10)
S1	0.0203 (2)	0.0203 (2)	0.0258 (2)	−0.00016 (15)	−0.00058 (17)	−0.00105 (15)
O1	0.0203 (6)	0.0225 (6)	0.0291 (6)	−0.0006 (5)	−0.0005 (5)	−0.0017 (5)
O2	0.0262 (6)	0.0301 (7)	0.0311 (7)	−0.0029 (6)	0.0008 (5)	0.0037 (5)
O3	0.0282 (6)	0.0279 (6)	0.0306 (7)	−0.0006 (6)	−0.0015 (6)	−0.0074 (6)
O4	0.0235 (6)	0.0256 (6)	0.0378 (7)	0.0016 (6)	−0.0023 (6)	0.0027 (5)
O1W	0.0273 (7)	0.0240 (6)	0.0287 (7)	0.0042 (5)	−0.0013 (6)	−0.0016 (5)
O2W	0.0244 (7)	0.0244 (6)	0.0399 (8)	0.0008 (6)	0.0046 (6)	0.0047 (6)
O3W	0.0221 (6)	0.0250 (6)	0.0371 (7)	0.0012 (6)	−0.0018 (6)	−0.0011 (5)
N1	0.0242 (7)	0.0253 (7)	0.0259 (7)	0.0006 (7)	−0.0010 (7)	0.0000 (6)
N2	0.0225 (7)	0.0251 (8)	0.0242 (7)	−0.0003 (6)	0.0009 (6)	0.0010 (6)
C1	0.0318 (11)	0.0275 (9)	0.0329 (10)	−0.0025 (8)	−0.0020 (8)	−0.0001 (8)
C2	0.0354 (11)	0.0292 (10)	0.0402 (11)	−0.0022 (9)	−0.0043 (9)	−0.0074 (8)
C3	0.0365 (11)	0.0404 (11)	0.0302 (10)	−0.0001 (10)	−0.0014 (10)	−0.0109 (8)
C4	0.0296 (10)	0.0363 (10)	0.0273 (9)	0.0006 (8)	−0.0011 (8)	−0.0032 (8)
C5	0.0423 (12)	0.0468 (12)	0.0231 (9)	−0.0016 (10)	0.0031 (8)	−0.0016 (9)
C6	0.0461 (13)	0.0474 (13)	0.0247 (10)	−0.0035 (11)	0.0058 (10)	0.0064 (9)
C7	0.0314 (10)	0.0347 (10)	0.0286 (9)	−0.0023 (9)	0.0038 (8)	0.0045 (8)
C8	0.0386 (12)	0.0341 (11)	0.0348 (11)	−0.0053 (10)	0.0064 (9)	0.0084 (9)
C9	0.0381 (11)	0.0270 (9)	0.0400 (11)	−0.0056 (9)	0.0029 (9)	0.0024 (9)
C10	0.0289 (10)	0.0288 (9)	0.0293 (10)	−0.0023 (8)	0.0015 (8)	−0.0021 (8)
C11	0.0234 (8)	0.0277 (9)	0.0244 (8)	0.0003 (7)	0.0011 (7)	0.0008 (7)
C12	0.0236 (8)	0.0285 (9)	0.0253 (9)	0.0011 (7)	−0.0005 (7)	−0.0006 (7)

Geometric parameters (Å, º) top

Co—O1	2.1386 (13)	C1—C2	1.399 (3)
Co—O1W	2.1110 (14)	C1—H1	0.9500
Co—O2W	2.0782 (15)	C2—C3	1.371 (3)
Co—O3W	2.1024 (14)	C2—H2	0.9500
Co—N1	2.1356 (15)	C3—C4	1.408 (3)
Co—N2	2.1453 (16)	C3—H3	0.9500
S1—O1	1.4997 (13)	C4—C12	1.411 (3)
S1—O2	1.4616 (14)	C4—C5	1.434 (3)
S1—O3	1.4813 (14)	C5—C6	1.351 (4)
S1—O4	1.4784 (14)	C5—H5	0.9500
O1W—H1W	0.837 (12)	C6—C7	1.436 (3)
O1W—H2W	0.834 (13)	C6—H6	0.9500
O2W—H3W	0.840 (13)	C7—C11	1.409 (3)
O2W—H4W	0.853 (12)	C7—C8	1.408 (3)
O3W—H5W	0.822 (12)	C8—C9	1.371 (3)
O3W—H6W	0.822 (13)	C8—H8	0.9500
N1—C1	1.331 (3)	C9—C10	1.397 (3)
N1—C12	1.356 (2)	C9—H9	0.9500
N2—C10	1.329 (3)	C10—H10	0.9500
N2—C11	1.361 (2)	C11—C12	1.441 (3)

O2W—Co—O3W	88.05 (6)	N1—C1—C2	122.9 (2)
O2W—Co—O1W	91.48 (6)	N1—C1—H1	118.6
O3W—Co—O1W	86.80 (6)	C2—C1—H1	118.6
O2W—Co—N1	93.13 (6)	C3—C2—C1	119.5 (2)
O3W—Co—N1	99.08 (6)	C3—C2—H2	120.3
O2W—Co—O1	92.59 (6)	C1—C2—H2	120.3
O1—Co—O3W	172.31 (5)	C2—C3—C4	119.26 (19)
O1W—Co—O1	85.53 (5)	C2—C3—H3	120.4
N1—Co—O1	88.54 (6)	C4—C3—H3	120.4
O1W—Co—N1	172.65 (6)	C3—C4—C12	117.42 (19)
O2W—Co—N2	166.55 (6)	C3—C4—C5	123.1 (2)
O3W—Co—N2	83.25 (6)	C12—C4—C5	119.4 (2)
O1W—Co—N2	98.23 (6)	C6—C5—C4	121.0 (2)
N1—Co—N2	78.21 (6)	C6—C5—H5	119.5
O1—Co—N2	97.41 (6)	C4—C5—H5	119.5
O2—S1—O4	110.56 (8)	C5—C6—C7	121.2 (2)
O2—S1—O3	110.35 (8)	C5—C6—H6	119.4
O4—S1—O3	110.04 (8)	C7—C6—H6	119.4
O2—S1—O1	109.85 (8)	C11—C7—C8	117.58 (19)
O4—S1—O1	107.51 (8)	C11—C7—C6	119.2 (2)
O3—S1—O1	108.47 (8)	C8—C7—C6	123.3 (2)
S1—O1—Co	126.85 (8)	C9—C8—C7	119.13 (19)
Co—O1W—H1W	110.3 (18)	C9—C8—H8	120.4
Co—O1W—H2W	128.2 (19)	C7—C8—H8	120.4
H1W—O1W—H2W	93 (3)	C8—C9—C10	119.6 (2)
Co—O2W—H3W	125 (2)	C8—C9—H9	120.2
Co—O2W—H4W	119 (2)	C10—C9—H9	120.2
H3W—O2W—H4W	106 (3)	N2—C10—C9	123.01 (19)
Co—O3W—H5W	117 (2)	N2—C10—H10	118.5
Co—O3W—H6W	132 (2)	C9—C10—H10	118.5
H5W—O3W—H6W	97 (3)	N2—C11—C7	122.72 (18)
C1—N1—C12	118.04 (17)	N2—C11—C12	117.50 (16)
C1—N1—Co	128.58 (14)	C7—C11—C12	119.78 (18)
C12—N1—Co	113.38 (12)	N1—C12—C4	122.85 (18)
C10—N2—C11	117.96 (16)	N1—C12—C11	117.73 (16)
C10—N2—Co	128.85 (14)	C4—C12—C11	119.43 (18)
C11—N2—Co	112.92 (12)

O2—S1—O1—Co	67.05 (11)	C10—N2—C11—C7	−1.0 (3)
O4—S1—O1—Co	−172.59 (9)	Co—N2—C11—C7	−175.48 (16)
O3—S1—O1—Co	−53.64 (11)	C10—N2—C11—C12	179.40 (17)
C12—N1—C1—C2	0.7 (3)	Co—N2—C11—C12	4.9 (2)
Co—N1—C1—C2	179.75 (16)	C8—C7—C11—N2	1.7 (3)
N1—C1—C2—C3	1.7 (3)	C6—C7—C11—N2	−178.4 (2)
C1—C2—C3—C4	−1.6 (3)	C8—C7—C11—C12	−178.70 (19)
C2—C3—C4—C12	−0.7 (3)	C6—C7—C11—C12	1.2 (3)
C2—C3—C4—C5	−178.1 (2)	C1—N1—C12—C4	−3.3 (3)
C3—C4—C5—C6	177.4 (2)	Co—N1—C12—C4	177.58 (15)
C12—C4—C5—C6	0.0 (4)	C1—N1—C12—C11	176.72 (17)
C4—C5—C6—C7	−0.2 (4)	Co—N1—C12—C11	−2.4 (2)
C5—C6—C7—C11	−0.4 (4)	C3—C4—C12—N1	3.2 (3)
C5—C6—C7—C8	179.5 (2)	C5—C4—C12—N1	−179.3 (2)
C11—C7—C8—C9	−1.1 (3)	C3—C4—C12—C11	−176.74 (19)
C6—C7—C8—C9	179.0 (2)	C5—C4—C12—C11	0.8 (3)
C7—C8—C9—C10	−0.1 (4)	N2—C11—C12—N1	−1.7 (3)
C11—N2—C10—C9	−0.3 (3)	C7—C11—C12—N1	178.67 (18)
Co—N2—C10—C9	173.15 (16)	N2—C11—C12—C4	178.26 (17)
C8—C9—C10—N2	0.9 (4)	C7—C11—C12—C4	−1.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O3	0.84 (2)	1.89 (2)	2.680 (2)	158 (2)
O1W—H2W···O1ⁱ	0.83 (1)	1.95 (1)	2.7818 (19)	172 (2)
O2W—H3W···O3ⁱⁱ	0.84 (2)	1.91 (2)	2.744 (2)	175 (3)
O2W—H4W···O4ⁱⁱⁱ	0.85 (1)	1.93 (1)	2.770 (2)	167 (3)
O3W—H5W···O4ⁱ	0.82 (2)	1.95 (2)	2.7548 (19)	168 (3)
O3W—H6W···O2ⁱⁱⁱ	0.82 (2)	1.84 (2)	2.6560 (19)	178 (3)
C3—H3···O2^iv	0.95	2.45	3.252 (3)	142

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, y+1/2, −z+1/2; (iii) x+1, y, z; (iv) x+1/2, −y+3/2, −z+1.

A summary of short interatomic contacts (Å) in (I)^a top

Contact	Distance	Symmetry operation
H2W···O1^b	1.81	-x + 1, y - 1/2, -z + 1/2
H3W···O3^b	1.76	-x + 1, y + 1/2, -z + 1/2
H4W···O4^b	1.81	x + 1, y, z
H5W···O4^b	1.79	-x + 1, y - 1/2, -z + 1/2
H6W···O2^b	1.67	x + 1, y, z
H1···O3	2.33	-x + 1, y + 1/2, -z + 1/2
H3···O2	2.35	x + 1/2, -y + 3/2, - z + 1
H6···O3W	2.51	x - 1/2, -y + 1/2, - z + 1
H10···O1	2.40	-x + 1, y - 1/2, - z + 1/2

Notes: (a) The interatomic distances are calculated in Crystal Explorer 17 (Turner et al., 2017) whereby the X—H bond lengths are adjusted to their neutron values; (b) these interactions correspond to conventional hydrogen bonds.

A summary of interaction energies (kJ mol^-1) calculated for (I) top

Contact	R (Å)	E_ele	E_pol	E_dis	E_rep	E_tot
O1W—H2W···O1ⁱ +	6.78	-330.8	-116.8	-49.6	180.1	-368.1
O3W—H5W···O4ⁱ +
O2W—H3W···O3ⁱⁱ +
C10—H10···O1ⁱ
O3W—H6W···O2ⁱⁱⁱ +	7.97	-198.3	-63.8	-16.4	121.0	-196.4
O2W—H4W···O4ⁱⁱⁱ
C5—H5···O3^v +	10.47	-46.2	-19.3	-9.8	7.8	-66.8
C6—H6···O4^v
C3—H3···O2^iv	7.64	-17.3	-30.2	-42.3	35.3	-55.7
C6—H6···O3W^vi	8.03	-2.3	-13.7	-37.7	24.0	-30.6

Symmetry operations: (i) -x + 1, y - 1/2, -z + 1/2; (ii) - x + 1, y + 1/2, - z + 1/2; (iii) x + 1, y, z; (iv) x + 1/2, -y + 3/2, -z + 1; (v) -x + 1/2, - y + 1, z + 1/2; (vi) x – 1/2, -y + 1/2, -z + 1.

Percentage contributions to intermolecular contacts on the Hirshfeld surface calculated for (I) top

Contact		Percentage contribution
	(I), M = Co	IJOQAA, M = Zn	RACWUO, M = Cd	XATNAH, M = Mn
H···H	28.6	30.1	27.6	27.2
H···O/O···H	44.5	43.3	45.8	45.9
H···C/C···H	19.5	19.1	19.2	19.1
C···C	5.7	5.7	5.2	5.6
Others	1.7	1.8	2.2	2.2

Footnotes

‡Additional correspondence author, e-mail: setifi_zouaoui@yahoo.fr.

Funding information

FS gratefully acknowledges the Algerian Ministère de l'Enseignement Supérieur et de la Recherche Scientifique (MESRS), the Direction Générale de la Recherche Scientifique et du Développement Technologique (DG–RSDT) as well as the Université Ferhat Abbas Sétif 1 for financial support. The Canadian Foundation for Innovation is thanked for the support of the Metaljet instrument. Crystallographic research at Sunway University is supported by Sunway University Sdn Bhd (Grant no. STR-RCTR-RCCM-001-2019).

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