Di­aqua­bis­[4-(di­methyl­amino)pyridine-κN1]bis­[2-(1,3-dioxo-2,3-di­hydro-1H-isoindol-2-yl)acetato-κO1]cobalt(II)

Makouf, N.; Chouiter, A.; Bouzidi Mousser, H.; Djedouani, A.; Fleutot, S.; François, M.

doi:10.1107/S2414314619001433

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 4| Part 1| January 2019| x190143

https://doi.org/10.1107/S2414314619001433

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Diaquabis[4-(dimethylamino)pyridine-κN¹]bis[2-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)acetato-κO¹]cobalt(II)

Naouel Makouf,^a Aziza Chouiter,^a Henia Bouzidi Mousser,^a,^b ^* Amel Djedouani,^a,^b Solenne Fleutot ^c and Michel François ^c

^aLaboratoire de Physicochimie Analytique et Cristallochimie de Matériaux, Organométalliques et Biomoléculaires, Université des Frères Mentouri Constantine 1, 25000 Constantine, Algeria, ^bEcole Normale Supérieure de Constantine Assia Djebar, Ville Universitaire Ali Mendjeli, Constantine, Algeria, and ^cInstitut Jean Lamour, Campus Artem, 2 allée André Guinier, BP 50840, 54011, Nancy Cedex, France
^*Correspondence e-mail: bouzidi_henia@yahoo.fr

Edited by D.-J. Xu, Zhejiang University (Yuquan Campus), China (Received 7 January 2019; accepted 25 January 2019; online 31 January 2019)

In the mononuclear title complex, [Co(C₁₀H₆NO₄)₂(C₇H₁₀N₂)₂(H₂O)₂], the Co^II ion is located on an inversion centre and has a distorted octahedral coordination geometry of type CoN₂O₄ by two N atoms from the two 4-(dimethylamino)pyridine (DMAP) ligands, two carboxylate O atoms from the two deprotonated N-phthaloylglycine (Nphgly) ligands [systematic name: 2-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)acetate] and two coordination water molecules. In the crystal, O—H⋯O, C—H⋯O hydrogen bonds and π–π stacking interactions link the molecules into the supramolecular structure.

Keywords: crystal structure; phthaloglycine; cobalt(II) complex.

CCDC reference: 1893566

Structure description

Paramagnetic materials and extended structures based on transition metals have found wide applications in molecular magnetism (Pavlishchuk et al., 2010 , 2011 ; Moroz et al., 2012 ). The Lewis base 4-dimethylaminopyridine (DMAP), a derivative of pyridine, finds use as a homogeneous catalyst in cellulose acylation for the synthesis of biodegradable plastics (Satgé et al., 2004 ). DMAP is also known to form transition-metal complexes which exhibit luminescence properties (Araki et al., 2005 ; Liu et al., 2015 ). The possibility of combining the DMAP ligand with a wide variety of co-ligands leads to an extensive variety of coordination modes. We report here the synthesis and crystal structure of a cobalt(II) complex with 4-(dimethylamino)pyridine and N-phthaloylglycine.

In the title complex, the cobalt(II) ion is located on an inversion center. The complex comprises two deprotonated N-phthaloylglycine ligands in a monodentate coordination mode and two 4-(dimethylamino)pyridine ligands. The slightly distorted coordination sphere CoN₂O₄ coordination sphere is completed by two aqua ligands (Fig. 1). The four oxygen atoms occupy the equatorial plane of the complex in a trans configuration and the DMAP ligands are coordinated through their N atoms in the axial positions. The Co—N bond length of 2.1293 (16) Å is in agreement with those retrieved from literature (Guenifa et al., 2013 ). The DMAP ligands are planar. The Co—O bond length of the Nphgly ligand is 2.0984 (13) Å and is shorter than that of the terminal aqua ligand of 2.1533 (14) Å. This is expected and is in agreement with bond lengths reported in the related structure of [Co(C₅HF₆O₂)₂(H₂O)₂]·2H₂O (Tominaga & Mochida, 2017 ). The dihedral angles formed between the mean planes through the four O atoms and the DMAP ring is 89.79 (1)°. Intramolecular O—H⋯O hydrogen bonding is observed between the carboxylate oxygen atoms and the coordinating water molecules, generating an S(6) ring motif.

Figure 1
The molecular structure of the title compound with displacement spheres drawn at the 30% probability level. H atoms are shown as spheres of arbitrary radius.

The complex cations are connected via C—H⋯O and O—H⋯O hydrogen bonds into infinite chains parallel to [100] (Fig. 2, Table 1). The O—H⋯O hydrogen bonds generate R₂²(18) motifs (Fig. 2). There are face-to-face π–π interactions between the benzene ring of the Nphgly ligand and the pyridine ring [Cg3⋯Cg2(−1 + x, y, z) = 3.735 (7) Å; Cg2 and Cg3 are the centroids of the NA1/CA11–CA15 and C4A–CA9 rings, respectively] (Fig. 3). This combination of hydrogen bonds and stacking interactions builds a three-dimensional network structure.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H11W⋯O2A	0.86 (1)	1.83 (1)	2.648 (2)	158 (2)
O1W—H21W⋯O3Aⁱ	0.85 (1)	2.02 (1)	2.853 (2)	168 (2)
C14A—H14A⋯O2Aⁱⁱ	0.93	2.40	3.160 (3)	139
Symmetry codes: (i) -x, -y+2, -z+2; (ii) x+1, y, z.

Figure 2
Partial view of the crystal structure of the title compound showing the formation of R₂²(18) rings. The C—H⋯O and O—H⋯O hydrogen bonds are shown as dashed lines.

Figure 3
π–π interactions (dashed lines) between the 4-(dimethylamino)pyridine and benzene rings of N-phthaloylglycine in the title compound [symmetry codes: (i) = −1 + x, y, z; (ii) = 1 + x, y, z].

Synthesis and crystallization

CoCl₂·6H₂O (0.237 g, 1 mmol) was dissolved in an ethanol solution (20 ml). 4-(Dimethylamino)-pyridine (0.122 g, 1 mmol) was added to this solution and the mixture was stirred for 15 min to obtain a blue solution. Then N-phthaloylglycine (0.205 g, 1 mmol) was added and the mixture was stirred for additional 20 min. Single crystals suitable for X-ray diffraction were obtained from a methanol solution of the title complex by slow evaporation.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	[Co(C₁₀H₆NO₄)₂(C₇H₁₀N₂)₂(H₂O)₂]
M_r	747.62
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	293
a, b, c (Å)	8.6830 (9), 10.2560 (11), 11.2980 (12)
α, β, γ (°)	83.547 (3), 72.194 (3), 68.901 (3)
V (Å³)	893.70 (17)
Z	1
Radiation type	Mo Kα
μ (mm⁻¹)	0.54
Crystal size (mm)	0.10 × 0.09 × 0.08

Data collection
Diffractometer	Bruker APEXII QUAZAR CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2004 )
T_min, T_max	0.950, 0.970
No. of measured, independent and observed [I > 2σ(I)] reflections	22559, 4629, 3658
R_int	0.060
(sin θ/λ)_max (Å⁻¹)	0.677

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.114, 1.05
No. of reflections	4629
No. of parameters	238
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.23
Computer programs: APEX2 and SAINT (Bruker, 2004), SHELXS97 and SHELXL97 (Sheldrick, 2008 ), ORTEP-3 for Windows and WinGX (Farrugia, 2012 ), Mercury (Macrae et al., 2008 ) and POVRay (Persistence of Vision Team, 2004 ).

Structural data

CCDC reference: 1893566

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314619001433/xu4038sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314619001433/xu4038Isup2.hkl

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012), Mercury (Macrae et al., 2008) and POVRay (Persistence of Vision Team, 2004).

\ Diaquabis[4-(dimethylamino)pyridine-κN¹]bis[2-(1,3-dioxo-2,3-\ dihydro-1H-isoindol-2-yl)acetato-κO¹]cobalt(II) top

Crystal data top

[Co(C₁₀H₆NO₄)₂(C₇H₁₀N₂)₂(H₂O)₂]	Z = 1
M_r = 747.62	F(000) = 389
Triclinic, P1	D_x = 1.389 Mg m⁻³
a = 8.6830 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.2560 (11) Å	Cell parameters from 2690 reflections
c = 11.2980 (12) Å	θ = 1.9–28.8°
α = 83.547 (3)°	µ = 0.54 mm⁻¹
β = 72.194 (3)°	T = 293 K
γ = 68.901 (3)°	Prism, blue
V = 893.70 (17) Å³	0.1 × 0.09 × 0.08 mm

Data collection top

Bruker APEXII QUAZAR CCD diffractometer	3658 reflections with I > 2σ(I)
Radiation source: ImuS	R_int = 0.060
f\ and ω scans	θ_max = 28.8°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −11→11
T_min = 0.950, T_max = 0.970	k = −13→13
22559 measured reflections	l = −15→15
4629 independent reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0463P)² + 0.3707P] where P = (F_o² + 2F_c²)/3
4629 reflections	(Δ/σ)_max < 0.001
238 parameters	Δρ_max = 0.32 e Å⁻³
3 restraints	Δρ_min = −0.23 e Å⁻³

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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Co1	0.5000	1.0000	1.0000	0.03061 (12)
O1A	0.45480 (17)	0.99688 (14)	0.82838 (12)	0.0374 (3)
O1W	0.24026 (17)	1.13925 (15)	1.07614 (13)	0.0390 (3)
H11W	0.195 (3)	1.152 (3)	1.0160 (14)	0.059*
H21W	0.176 (3)	1.113 (3)	1.1393 (13)	0.059*
N1A	0.5758 (2)	1.17785 (17)	0.93996 (15)	0.0369 (4)
N3A	0.1690 (2)	1.0721 (2)	0.63725 (15)	0.0414 (4)
O2A	0.1816 (2)	1.1375 (2)	0.85983 (15)	0.0614 (5)
C3A	0.0278 (3)	1.0292 (2)	0.66807 (18)	0.0392 (4)
O3A	0.0192 (2)	0.92469 (18)	0.72650 (16)	0.0568 (4)
C4A	−0.1014 (2)	1.1350 (2)	0.61425 (18)	0.0382 (4)
C9A	−0.0343 (3)	1.2380 (2)	0.55858 (19)	0.0413 (5)
O4A	0.2396 (2)	1.2623 (2)	0.54431 (19)	0.0698 (5)
C15A	0.7243 (3)	1.1837 (2)	0.9467 (2)	0.0398 (4)
H15A	0.7944	1.1068	0.9803	0.048*
C1A	0.3167 (2)	1.0511 (2)	0.79943 (17)	0.0360 (4)
C10A	0.1395 (3)	1.2001 (2)	0.57571 (19)	0.0445 (5)
C13A	0.6808 (3)	1.4125 (2)	0.85706 (19)	0.0446 (5)
C5A	−0.2617 (3)	1.1408 (3)	0.6127 (2)	0.0505 (6)
H5A	−0.3076	1.0725	0.6510	0.061*
C2A	0.3226 (3)	1.0008 (3)	0.6763 (2)	0.0486 (5)
H2A1	0.4207	1.0130	0.6126	0.058*
H2A2	0.3406	0.9016	0.6828	0.058*
C11A	0.4790 (3)	1.2922 (2)	0.8915 (2)	0.0422 (5)
H11A	0.3746	1.2926	0.8852	0.051*
C6A	−0.3516 (3)	1.2532 (3)	0.5512 (3)	0.0628 (7)
H6A	−0.4598	1.2600	0.5476	0.075*
C14A	0.7810 (3)	1.2935 (2)	0.9083 (2)	0.0462 (5)
H14A	0.8862	1.2895	0.9161	0.055*
N2A	0.7346 (3)	1.5225 (2)	0.8160 (2)	0.0621 (6)
C12A	0.5239 (3)	1.4080 (2)	0.8508 (2)	0.0473 (5)
H12A	0.4501	1.4839	0.8189	0.057*
C8A	−0.1236 (3)	1.3495 (3)	0.4985 (2)	0.0576 (6)
H8A	−0.0784	1.4187	0.4614	0.069*
C7A	−0.2841 (3)	1.3549 (3)	0.4955 (3)	0.0665 (7)
H7A	−0.3476	1.4288	0.4549	0.080*
C17A	0.8965 (4)	1.5217 (3)	0.8262 (3)	0.0851 (10)
H17A	0.9144	1.6070	0.7923	0.128*
H17B	0.9885	1.4437	0.7809	0.128*
H17C	0.8944	1.5138	0.9121	0.128*
C16A	0.6279 (5)	1.6452 (3)	0.7642 (3)	0.0781 (9)
H16A	0.6856	1.7122	0.7397	0.117*
H16B	0.5198	1.6858	0.8257	0.117*
H16C	0.6076	1.6186	0.6931	0.117*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.03132 (19)	0.03084 (19)	0.02919 (19)	−0.00865 (14)	−0.01154 (14)	0.00303 (13)
O1A	0.0352 (7)	0.0442 (8)	0.0327 (7)	−0.0094 (6)	−0.0153 (6)	0.0023 (6)
O1W	0.0374 (7)	0.0412 (8)	0.0356 (7)	−0.0113 (6)	−0.0099 (6)	0.0015 (6)
N1A	0.0391 (9)	0.0342 (8)	0.0355 (9)	−0.0106 (7)	−0.0113 (7)	0.0027 (7)
N3A	0.0377 (9)	0.0592 (11)	0.0321 (9)	−0.0177 (8)	−0.0166 (7)	0.0031 (8)
O2A	0.0413 (9)	0.0829 (12)	0.0446 (9)	0.0075 (8)	−0.0197 (7)	−0.0162 (8)
C3A	0.0415 (10)	0.0486 (11)	0.0269 (9)	−0.0165 (9)	−0.0067 (8)	−0.0030 (8)
O3A	0.0597 (10)	0.0536 (10)	0.0508 (10)	−0.0212 (8)	−0.0081 (8)	0.0090 (8)
C4A	0.0353 (10)	0.0508 (12)	0.0287 (9)	−0.0143 (9)	−0.0077 (8)	−0.0069 (8)
C9A	0.0408 (11)	0.0518 (12)	0.0333 (10)	−0.0160 (9)	−0.0137 (8)	0.0004 (9)
O4A	0.0642 (11)	0.0924 (14)	0.0743 (13)	−0.0521 (11)	−0.0290 (10)	0.0267 (11)
C15A	0.0382 (10)	0.0334 (10)	0.0438 (11)	−0.0092 (8)	−0.0105 (9)	0.0008 (8)
C1A	0.0334 (9)	0.0418 (10)	0.0308 (10)	−0.0093 (8)	−0.0117 (8)	0.0026 (8)
C10A	0.0456 (12)	0.0620 (14)	0.0334 (10)	−0.0264 (10)	−0.0149 (9)	0.0069 (9)
C13A	0.0542 (13)	0.0338 (10)	0.0352 (11)	−0.0148 (9)	0.0036 (9)	−0.0065 (8)
C5A	0.0376 (11)	0.0687 (15)	0.0472 (13)	−0.0214 (10)	−0.0056 (9)	−0.0155 (11)
C2A	0.0405 (11)	0.0639 (14)	0.0393 (11)	−0.0081 (10)	−0.0187 (9)	−0.0050 (10)
C11A	0.0429 (11)	0.0392 (10)	0.0413 (11)	−0.0100 (9)	−0.0138 (9)	0.0039 (8)
C6A	0.0345 (12)	0.090 (2)	0.0603 (16)	−0.0078 (12)	−0.0171 (11)	−0.0200 (14)
C14A	0.0395 (11)	0.0405 (11)	0.0548 (13)	−0.0141 (9)	−0.0059 (10)	−0.0063 (9)
N2A	0.0835 (16)	0.0378 (10)	0.0592 (13)	−0.0285 (10)	−0.0027 (11)	−0.0004 (9)
C12A	0.0577 (13)	0.0324 (10)	0.0412 (12)	−0.0062 (9)	−0.0120 (10)	0.0037 (8)
C8A	0.0572 (14)	0.0620 (15)	0.0525 (14)	−0.0174 (12)	−0.0219 (12)	0.0113 (11)
C7A	0.0504 (14)	0.0755 (18)	0.0601 (16)	0.0012 (13)	−0.0250 (12)	0.0009 (14)
C17A	0.086 (2)	0.0629 (18)	0.104 (3)	−0.0485 (17)	0.0064 (19)	−0.0085 (17)
C16A	0.120 (3)	0.0393 (13)	0.0609 (17)	−0.0300 (15)	−0.0058 (17)	0.0068 (12)

Geometric parameters (Å, º) top

Co1—O1A	2.0984 (13)	C13A—N2A	1.354 (3)
Co1—O1Aⁱ	2.0984 (13)	C13A—C14A	1.402 (3)
Co1—N1A	2.1293 (16)	C13A—C12A	1.404 (3)
Co1—N1Aⁱ	2.1293 (16)	C5A—C6A	1.387 (4)
Co1—O1Wⁱ	2.1533 (14)	C5A—H5A	0.9300
Co1—O1W	2.1533 (14)	C2A—H2A1	0.9700
O1A—C1A	1.254 (2)	C2A—H2A2	0.9700
O1W—H11W	0.859 (9)	C11A—C12A	1.369 (3)
O1W—H21W	0.848 (9)	C11A—H11A	0.9300
N1A—C15A	1.337 (3)	C6A—C7A	1.376 (4)
N1A—C11A	1.345 (2)	C6A—H6A	0.9300
N3A—C3A	1.383 (3)	C14A—H14A	0.9300
N3A—C10A	1.391 (3)	N2A—C17A	1.442 (4)
N3A—C2A	1.447 (3)	N2A—C16A	1.452 (4)
O2A—C1A	1.235 (2)	C12A—H12A	0.9300
C3A—O3A	1.208 (3)	C8A—C7A	1.385 (4)
C3A—C4A	1.482 (3)	C8A—H8A	0.9300
C4A—C5A	1.377 (3)	C7A—H7A	0.9300
C4A—C9A	1.386 (3)	C17A—H17A	0.9600
C9A—C8A	1.371 (3)	C17A—H17B	0.9600
C9A—C10A	1.485 (3)	C17A—H17C	0.9600
O4A—C10A	1.203 (3)	C16A—H16A	0.9600
C15A—C14A	1.363 (3)	C16A—H16B	0.9600
C15A—H15A	0.9300	C16A—H16C	0.9600
C1A—C2A	1.518 (3)

O1A—Co1—O1Aⁱ	180.0	N2A—C13A—C12A	123.2 (2)
O1A—Co1—N1A	89.62 (6)	C14A—C13A—C12A	115.20 (19)
O1Aⁱ—Co1—N1A	90.38 (6)	C4A—C5A—C6A	117.0 (2)
O1A—Co1—N1Aⁱ	90.38 (6)	C4A—C5A—H5A	121.5
O1Aⁱ—Co1—N1Aⁱ	89.62 (6)	C6A—C5A—H5A	121.5
N1A—Co1—N1Aⁱ	180.0	N3A—C2A—C1A	114.20 (18)
O1A—Co1—O1Wⁱ	88.93 (5)	N3A—C2A—H2A1	108.7
O1Aⁱ—Co1—O1Wⁱ	91.07 (5)	C1A—C2A—H2A1	108.7
N1A—Co1—O1Wⁱ	91.28 (6)	N3A—C2A—H2A2	108.7
N1Aⁱ—Co1—O1Wⁱ	88.72 (6)	C1A—C2A—H2A2	108.7
O1A—Co1—O1W	91.07 (5)	H2A1—C2A—H2A2	107.6
O1Aⁱ—Co1—O1W	88.93 (5)	N1A—C11A—C12A	124.4 (2)
N1A—Co1—O1W	88.72 (6)	N1A—C11A—H11A	117.8
N1Aⁱ—Co1—O1W	91.28 (6)	C12A—C11A—H11A	117.8
O1Wⁱ—Co1—O1W	180.0	C7A—C6A—C5A	121.4 (2)
C1A—O1A—Co1	128.90 (13)	C7A—C6A—H6A	119.3
Co1—O1W—H11W	104.0 (17)	C5A—C6A—H6A	119.3
Co1—O1W—H21W	118.6 (17)	C15A—C14A—C13A	120.1 (2)
H11W—O1W—H21W	108.2 (14)	C15A—C14A—H14A	120.0
C15A—N1A—C11A	114.92 (18)	C13A—C14A—H14A	120.0
C15A—N1A—Co1	122.42 (13)	C13A—N2A—C17A	120.6 (2)
C11A—N1A—Co1	122.66 (14)	C13A—N2A—C16A	120.6 (3)
C3A—N3A—C10A	112.13 (17)	C17A—N2A—C16A	118.8 (2)
C3A—N3A—C2A	124.14 (19)	C11A—C12A—C13A	120.2 (2)
C10A—N3A—C2A	123.40 (19)	C11A—C12A—H12A	119.9
O3A—C3A—N3A	124.6 (2)	C13A—C12A—H12A	119.9
O3A—C3A—C4A	129.3 (2)	C9A—C8A—C7A	117.1 (3)
N3A—C3A—C4A	106.07 (17)	C9A—C8A—H8A	121.5
C5A—C4A—C9A	121.4 (2)	C7A—C8A—H8A	121.5
C5A—C4A—C3A	130.6 (2)	C6A—C7A—C8A	121.5 (2)
C9A—C4A—C3A	107.97 (17)	C6A—C7A—H7A	119.2
C8A—C9A—C4A	121.6 (2)	C8A—C7A—H7A	119.2
C8A—C9A—C10A	130.4 (2)	N2A—C17A—H17A	109.5
C4A—C9A—C10A	107.96 (18)	N2A—C17A—H17B	109.5
N1A—C15A—C14A	125.17 (19)	H17A—C17A—H17B	109.5
N1A—C15A—H15A	117.4	N2A—C17A—H17C	109.5
C14A—C15A—H15A	117.4	H17A—C17A—H17C	109.5
O2A—C1A—O1A	127.18 (18)	H17B—C17A—H17C	109.5
O2A—C1A—C2A	118.74 (17)	N2A—C16A—H16A	109.5
O1A—C1A—C2A	114.08 (17)	N2A—C16A—H16B	109.5
O4A—C10A—N3A	124.7 (2)	H16A—C16A—H16B	109.5
O4A—C10A—C9A	129.6 (2)	N2A—C16A—H16C	109.5
N3A—C10A—C9A	105.73 (17)	H16A—C16A—H16C	109.5
N2A—C13A—C14A	121.6 (2)	H16B—C16A—H16C	109.5

Symmetry code: (i) −x+1, −y+2, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H11W···O2A	0.86 (1)	1.83 (1)	2.648 (2)	158 (2)
O1W—H21W···O3Aⁱⁱ	0.85 (1)	2.02 (1)	2.853 (2)	168 (2)
C14A—H14A···O2Aⁱⁱⁱ	0.93	2.40	3.160 (3)	139

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

Acknowledgements

The authors acknowledge the Algerian Ministry of Higher Education and Scientific Research, the Algerian Directorate General for Scientific Research and Technological Development for support of this work and thank Professor Hebbachi Rabihe (Constantine 1 University) for providing the initial ligands.

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