5-Methyl-1-(4-methyl­phen­yl)-N′-[1-(1H-pyrrol-2-yl)ethyl­idene]-1H-1,2,3-triazole-4-carbohydrazide monohydrate

El-Hiti, G.A.; Abdel-Wahab, B.F.; Alotaibi, M.H.; Yousif, E.; Hegazy, A.S.; Kariuki, B.M.

doi:10.1107/S2414314618011628

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 3| Part 8| August 2018| x181162

https://doi.org/10.1107/S2414314618011628

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5-Methyl-1-(4-methylphenyl)-N′-[1-(1H-pyrrol-2-yl)ethylidene]-1H-1,2,3-triazole-4-carbohydrazide monohydrate

Gamal A. El-Hiti,^a ^* Bakr F. Abdel-Wahab,^b,^c Mohammad Hayal Alotaibi,^d Emad Yousif,^e Amany S. Hegazy ^f and Benson M. Kariuki ^f ‡

^aDepartment of Optometry, College of Applied Medical Sciences, King Saud University, PO Box 10219, Riyadh 11433, Saudi Arabia, ^bDepartment of Chemistry, College of Science and Humanities, Shaqra University, Duwadimi, Saudi Arabia, ^cApplied Organic Chemistry Department, National Research Centre, Dokki, Giza, Egypt, ^dNational Center for Petrochemicals Technology, King Abdulaziz City for Science and Technology, PO Box 6086, Riyadh 11442, Saudi Arabia, ^eDepartment of Chemistry, College of Science, Al-Nahrain University, Baghdad 64021, Iraq, and ^fSchool of Chemistry, Cardiff University, Main Building, Park Place, Cardiff CF10 3AT, UK
^*Correspondence e-mail: gelhiti@ksu.edu.sa

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 6 August 2018; accepted 16 August 2018; online 21 August 2018)

In the title hydrate, C₁₇H₁₈N₆O·H₂O, the twist angles between the least-squares planes of the pyrolyl/methyltriazolyl/tolyl groups are 11.4 (2) and 7.9 (1)°, respectively. In the crystal, centrosymmetric tetramers (two organic molecules and two water molecules) are linked by N—H⋯O and O—H⋯O hydrogen bonds. Weak aromatic π–π stacking interactions between the triazolyl rings [centroid–centroid separation = 3.6422 (10) Å] link the tetramers.

Keywords: crystal structure; pyrrole; carbohydrazide.

CCDC reference: 1862395

Structure description

Arylidene carbohydrazides have various biological activities (Almasirad et al., 2005 ; Bonacorso et al., 2012 ; Hernández-Vázquez et al., 2016 ; Leite et al., 1999 ; Lima et al., 2000 ). As part of our studies in this area, we now describe the synthesis and structure of the title hydrate.

The asymmetric unit consists of a 1,2,3-triazole-4-carbohydrazide molecule and a water molecule (Fig. 1). The twist angles between the least-squares planes of the pyrolyl/methyltriazolyl/tolyl groups are 11.4 (2) and 7.9 (1)°, respectively. In the crystal, the pyrolyl group donates an N—H⋯O hydrogen bond to the water molecule, which in turn donates O—H hydrogen bonds to two neighbouring molecules, thereby linking them (Table 1, Fig. 2) into a centrosymmetric tetramer. Organic molecules related by inversion symmetry are arranged in pairs with the centroids of their triazolyl rings 3.6422 (10) Å apart. The pairs are stacked such that the closest distance between the centroids of triazolyl groups of neighbouring pairs is 3.967 (2) Å.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2ⁱ	0.86	1.98	2.838 (2)	176
O2—H1O⋯O1ⁱⁱ	0.87 (4)	1.96 (4)	2.822 (2)	174 (3)
O2—H2O⋯N2ⁱ	0.79 (4)	2.43 (4)	2.966 (3)	126 (3)
O2—H2O⋯O1ⁱ	0.79 (4)	2.20 (4)	2.961 (2)	162 (3)
Symmetry codes: (i) -x+1, -y+1, -z; (ii) x-1, y, z.

Figure 1
The molecular structure, showing 50% probability displacement ellipsoids.

Figure 2
A segment of the crystal structure, showing N—H⋯O and O—H⋯O hydrogen bonds and centroid–centroid contacts as dashed lines. Some H atoms have been omitted for clarity.

Synthesis and crystallization

The title compound (yield 85%) was synthesized from reaction of a mixture of 5-methyl-1-(4-methylphenyl)-1H-1,2,3-triazole-4-carbohydrazide and 1-(1H-pyrrol-2-yl)ethanone in boiling ethanol containing a few drops of acetic acid for 4 h. The crude product obtained was recrystallized from dimethylformamide solution to give colourless crystals. The water molecule of crystallization was presumably absorbed from the atmosphere.

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	C₁₇H₁₈N₆O·H₂O
M_r	340.39
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	296
a, b, c (Å)	7.3968 (8), 10.6475 (9), 12.7769 (13)
α, β, γ (°)	106.577 (9), 100.809 (9), 108.208 (9)
V (Å³)	872.83 (16)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.09
Crystal size (mm)	0.26 × 0.18 × 0.15

Data collection
Diffractometer	Rigaku Oxford Diffraction SuperNova, Dual, Cu at zero, Atlas
Absorption correction	Gaussian (CrysAlis PRO; Rigaku OD, 2015 $[Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ )
T_min, T_max	0.497, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	7305, 4129, 2871
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.699

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.155, 1.05
No. of reflections	4129
No. of parameters	237
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.27
Computer programs: CrysAlis PRO (Rigaku OD, 2015 $[Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ ), SHELXS97 (Sheldrick, 2008 ), SHELXL2018 (Sheldrick, 2015 ), ORTEP-3 for Windows and WinGX (Farrugia, 2012 ) and CHEMDRAW Ultra (Cambridge Soft, 2001 ).

Structural data

CCDC reference: 1862395

Crystal structure: contains datablocks I, bmk1745. DOI: https://doi.org/10.1107/S2414314618011628/hb4251sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314618011628/hb4251Isup2.hkl

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows and WinGX (Farrugia, 2012); software used to prepare material for publication: ORTEP-3 for Windows and WinGX (Farrugia, 2012), and CHEMDRAW Ultra (Cambridge Soft, 2001).

5-Methyl-1-(4-methylphenyl)-N'-[1-(1H-pyrrol-2-yl)ethylidene]-1H-1,2,3-triazole-4-carbohydrazide monohydrate top

Crystal data top

C₁₇H₁₈N₆O·H₂O	Z = 2
M_r = 340.39	F(000) = 360
Triclinic, P1	D_x = 1.295 Mg m⁻³
a = 7.3968 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.6475 (9) Å	Cell parameters from 2273 reflections
c = 12.7769 (13) Å	θ = 3.4–28.7°
α = 106.577 (9)°	µ = 0.09 mm⁻¹
β = 100.809 (9)°	T = 296 K
γ = 108.208 (9)°	Block, colourless
V = 872.83 (16) Å³	0.26 × 0.18 × 0.15 mm

Data collection top

Rigaku Oxford Diffraction SuperNova, Dual, Cu at zero, Atlas diffractometer	2871 reflections with I > 2σ(I)
ω scans	R_int = 0.022
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2015)	θ_max = 29.8°, θ_min = 3.0°
T_min = 0.497, T_max = 1.000	h = −9→9
7305 measured reflections	k = −14→13
4129 independent reflections	l = −16→14

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.057	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.155	w = 1/[σ²(F_o²) + (0.0585P)² + 0.2675P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
4129 reflections	Δρ_max = 0.21 e Å⁻³
237 parameters	Δρ_min = −0.27 e Å⁻³
0 restraints

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. Water H atoms were located on the difference Fourier map and refined freely. The rest of the H atoms were placed in calculated positions and refined using a riding model. Methyl C—H bonds were fixed at 0.96 Å, with displacement parameters 1.5 times U_eq(C), and were allowed to spin about the C—C bond. N—H bonds were fixed at 0.86 Å and aromatic C—H distances were set at 0.93 Å and their U_iso values set at 1.2 times the U_eq for the atoms to which they are bonded.

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

	x	y	z	U_iso*/U_eq
C1	0.4498 (4)	0.5591 (2)	−0.34752 (19)	0.0624 (6)
H1	0.552068	0.614290	−0.367621	0.075*
C2	0.2509 (4)	0.5212 (3)	−0.3952 (2)	0.0674 (7)
H2	0.192987	0.545682	−0.453369	0.081*
C3	0.1493 (3)	0.4384 (2)	−0.34062 (18)	0.0582 (6)
H3	0.011555	0.397898	−0.355871	0.070*
C4	0.2908 (3)	0.4282 (2)	−0.26023 (15)	0.0449 (4)
C5	0.2718 (3)	0.3527 (2)	−0.18161 (15)	0.0435 (4)
C6	0.0678 (3)	0.2643 (3)	−0.1852 (2)	0.0661 (6)
H6A	0.050998	0.166304	−0.208278	0.099*
H6B	−0.030420	0.274780	−0.239134	0.099*
H6C	0.051649	0.295101	−0.110493	0.099*
C7	0.5842 (3)	0.28246 (19)	0.01528 (15)	0.0427 (4)
C8	0.5431 (3)	0.19870 (19)	0.08797 (15)	0.0437 (4)
C9	0.6700 (3)	0.1633 (2)	0.15650 (15)	0.0447 (4)
C10	0.8839 (3)	0.1866 (3)	0.1746 (2)	0.0644 (6)
H10A	0.965436	0.277622	0.233966	0.097*
H10B	0.915867	0.184061	0.104786	0.097*
H10C	0.908864	0.113237	0.196794	0.097*
C11	0.5936 (3)	0.02833 (19)	0.28757 (15)	0.0423 (4)
C12	0.4664 (3)	−0.1064 (2)	0.27027 (16)	0.0473 (5)
H12	0.357886	−0.158025	0.204142	0.057*
C13	0.5012 (3)	−0.1642 (2)	0.35192 (17)	0.0510 (5)
H13	0.414885	−0.255287	0.340156	0.061*
C14	0.6612 (3)	−0.0901 (2)	0.45079 (17)	0.0493 (5)
C15	0.7877 (3)	0.0454 (2)	0.46619 (17)	0.0537 (5)
H15	0.897338	0.096469	0.531771	0.064*
C16	0.7543 (3)	0.1060 (2)	0.38601 (17)	0.0514 (5)
H16	0.838664	0.197805	0.398139	0.062*
C17	0.6964 (4)	−0.1568 (3)	0.5383 (2)	0.0680 (6)
H17A	0.574689	−0.194456	0.555808	0.102*
H17B	0.797874	−0.086174	0.606917	0.102*
H17C	0.738952	−0.232303	0.507897	0.102*
N1	0.4733 (3)	0.50299 (17)	−0.26600 (14)	0.0512 (4)
H1A	0.586128	0.512927	−0.224096	0.061*
N2	0.4359 (2)	0.36382 (16)	−0.11682 (13)	0.0447 (4)
N3	0.4194 (2)	0.28847 (17)	−0.04530 (13)	0.0463 (4)
H3A	0.304451	0.245452	−0.039329	0.056*
N4	0.3558 (2)	0.14459 (19)	0.09563 (14)	0.0528 (4)
N5	0.3573 (2)	0.07814 (19)	0.16659 (15)	0.0539 (4)
N6	0.5496 (2)	0.08967 (17)	0.20462 (13)	0.0455 (4)
O1	0.75210 (19)	0.33899 (15)	0.00833 (11)	0.0534 (4)
O2	0.1638 (3)	0.4799 (3)	0.1289 (2)	0.1062 (9)
H1O	0.036 (6)	0.435 (4)	0.097 (3)	0.130 (13)*
H2O	0.211 (5)	0.529 (4)	0.097 (3)	0.109 (11)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0743 (16)	0.0615 (13)	0.0618 (13)	0.0252 (12)	0.0203 (11)	0.0391 (11)
C2	0.0841 (18)	0.0699 (15)	0.0594 (13)	0.0369 (13)	0.0114 (12)	0.0388 (12)
C3	0.0546 (13)	0.0656 (14)	0.0585 (12)	0.0275 (11)	0.0077 (10)	0.0301 (11)
C4	0.0470 (11)	0.0474 (11)	0.0436 (10)	0.0207 (9)	0.0111 (8)	0.0205 (8)
C5	0.0409 (10)	0.0469 (10)	0.0433 (9)	0.0165 (8)	0.0106 (8)	0.0196 (8)
C6	0.0405 (12)	0.0849 (16)	0.0720 (14)	0.0128 (11)	0.0108 (10)	0.0445 (13)
C7	0.0401 (10)	0.0453 (10)	0.0398 (9)	0.0114 (8)	0.0089 (7)	0.0192 (8)
C8	0.0391 (10)	0.0479 (11)	0.0435 (9)	0.0120 (8)	0.0099 (7)	0.0233 (8)
C9	0.0410 (10)	0.0489 (11)	0.0462 (10)	0.0129 (8)	0.0121 (8)	0.0262 (8)
C10	0.0452 (12)	0.0883 (17)	0.0806 (15)	0.0278 (11)	0.0224 (11)	0.0565 (14)
C11	0.0425 (10)	0.0481 (10)	0.0459 (10)	0.0197 (8)	0.0165 (8)	0.0268 (8)
C12	0.0466 (11)	0.0469 (11)	0.0493 (10)	0.0147 (9)	0.0176 (8)	0.0212 (9)
C13	0.0554 (12)	0.0463 (11)	0.0635 (12)	0.0203 (9)	0.0286 (10)	0.0302 (10)
C14	0.0599 (12)	0.0588 (12)	0.0545 (11)	0.0358 (10)	0.0305 (10)	0.0342 (10)
C15	0.0567 (12)	0.0567 (12)	0.0508 (11)	0.0242 (10)	0.0111 (9)	0.0252 (10)
C16	0.0511 (12)	0.0452 (11)	0.0563 (11)	0.0137 (9)	0.0104 (9)	0.0256 (9)
C17	0.0860 (17)	0.0842 (17)	0.0734 (15)	0.0506 (14)	0.0406 (13)	0.0550 (13)
N1	0.0508 (10)	0.0571 (10)	0.0542 (9)	0.0212 (8)	0.0144 (7)	0.0332 (8)
N2	0.0423 (9)	0.0525 (9)	0.0456 (8)	0.0172 (7)	0.0126 (7)	0.0287 (7)
N3	0.0361 (8)	0.0582 (10)	0.0503 (9)	0.0141 (7)	0.0125 (7)	0.0333 (8)
N4	0.0420 (9)	0.0660 (11)	0.0572 (10)	0.0171 (8)	0.0131 (7)	0.0382 (9)
N5	0.0401 (9)	0.0675 (11)	0.0618 (10)	0.0165 (8)	0.0142 (7)	0.0405 (9)
N6	0.0388 (9)	0.0521 (9)	0.0504 (9)	0.0147 (7)	0.0123 (7)	0.0298 (7)
O1	0.0375 (7)	0.0699 (9)	0.0561 (8)	0.0135 (7)	0.0118 (6)	0.0375 (7)
O2	0.0396 (10)	0.147 (2)	0.1405 (19)	0.0047 (11)	0.0041 (11)	0.1141 (18)

Geometric parameters (Å, º) top

C1—N1	1.351 (2)	C10—H10C	0.9600
C1—C2	1.360 (3)	C11—C12	1.375 (3)
C1—H1	0.9300	C11—C16	1.382 (3)
C2—C3	1.400 (3)	C11—N6	1.433 (2)
C2—H2	0.9300	C12—C13	1.377 (3)
C3—C4	1.377 (3)	C12—H12	0.9300
C3—H3	0.9300	C13—C14	1.380 (3)
C4—N1	1.364 (3)	C13—H13	0.9300
C4—C5	1.455 (2)	C14—C15	1.386 (3)
C5—N2	1.285 (2)	C14—C17	1.511 (3)
C5—C6	1.492 (3)	C15—C16	1.382 (3)
C6—H6A	0.9600	C15—H15	0.9300
C6—H6B	0.9600	C16—H16	0.9300
C6—H6C	0.9600	C17—H17A	0.9600
C7—O1	1.232 (2)	C17—H17B	0.9600
C7—N3	1.346 (2)	C17—H17C	0.9600
C7—C8	1.470 (2)	N1—H1A	0.8600
C8—N4	1.359 (2)	N2—N3	1.376 (2)
C8—C9	1.375 (2)	N3—H3A	0.8600
C9—N6	1.353 (2)	N4—N5	1.300 (2)
C9—C10	1.484 (3)	N5—N6	1.368 (2)
C10—H10A	0.9600	O2—H1O	0.87 (4)
C10—H10B	0.9600	O2—H2O	0.79 (4)

N1—C1—C2	108.3 (2)	C12—C11—N6	118.61 (16)
N1—C1—H1	125.8	C16—C11—N6	120.64 (16)
C2—C1—H1	125.8	C11—C12—C13	119.31 (18)
C1—C2—C3	107.43 (18)	C11—C12—H12	120.3
C1—C2—H2	126.3	C13—C12—H12	120.3
C3—C2—H2	126.3	C12—C13—C14	121.59 (18)
C4—C3—C2	107.4 (2)	C12—C13—H13	119.2
C4—C3—H3	126.3	C14—C13—H13	119.2
C2—C3—H3	126.3	C13—C14—C15	118.07 (17)
N1—C4—C3	107.16 (17)	C13—C14—C17	120.34 (19)
N1—C4—C5	121.31 (16)	C15—C14—C17	121.6 (2)
C3—C4—C5	131.50 (19)	C16—C15—C14	121.31 (19)
N2—C5—C4	116.18 (17)	C16—C15—H15	119.3
N2—C5—C6	125.02 (17)	C14—C15—H15	119.3
C4—C5—C6	118.75 (16)	C11—C16—C15	119.06 (18)
C5—C6—H6A	109.5	C11—C16—H16	120.5
C5—C6—H6B	109.5	C15—C16—H16	120.5
H6A—C6—H6B	109.5	C14—C17—H17A	109.5
C5—C6—H6C	109.5	C14—C17—H17B	109.5
H6A—C6—H6C	109.5	H17A—C17—H17B	109.5
H6B—C6—H6C	109.5	C14—C17—H17C	109.5
O1—C7—N3	123.18 (16)	H17A—C17—H17C	109.5
O1—C7—C8	123.42 (16)	H17B—C17—H17C	109.5
N3—C7—C8	113.38 (16)	C1—N1—C4	109.67 (17)
N4—C8—C9	109.63 (15)	C1—N1—H1A	125.2
N4—C8—C7	120.37 (16)	C4—N1—H1A	125.2
C9—C8—C7	129.99 (17)	C5—N2—N3	116.60 (16)
N6—C9—C8	103.14 (16)	C7—N3—N2	119.63 (15)
N6—C9—C10	124.59 (16)	C7—N3—H3A	120.2
C8—C9—C10	132.18 (17)	N2—N3—H3A	120.2
C9—C10—H10A	109.5	N5—N4—C8	109.18 (15)
C9—C10—H10B	109.5	N4—N5—N6	106.59 (15)
H10A—C10—H10B	109.5	C9—N6—N5	111.46 (14)
C9—C10—H10C	109.5	C9—N6—C11	130.64 (16)
H10A—C10—H10C	109.5	N5—N6—C11	117.88 (14)
H10B—C10—H10C	109.5	H1O—O2—H2O	111 (3)
C12—C11—C16	120.66 (16)

N1—C1—C2—C3	−0.1 (3)	N6—C11—C16—C15	177.54 (18)
C1—C2—C3—C4	0.0 (3)	C14—C15—C16—C11	−1.4 (3)
C2—C3—C4—N1	0.1 (2)	C2—C1—N1—C4	0.2 (3)
C2—C3—C4—C5	−178.0 (2)	C3—C4—N1—C1	−0.2 (2)
N1—C4—C5—N2	1.6 (3)	C5—C4—N1—C1	178.16 (18)
C3—C4—C5—N2	179.5 (2)	C4—C5—N2—N3	−177.59 (16)
N1—C4—C5—C6	−175.7 (2)	C6—C5—N2—N3	−0.5 (3)
C3—C4—C5—C6	2.2 (3)	O1—C7—N3—N2	−1.8 (3)
O1—C7—C8—N4	177.01 (19)	C8—C7—N3—N2	179.80 (15)
N3—C7—C8—N4	−4.5 (3)	C5—N2—N3—C7	172.56 (17)
O1—C7—C8—C9	−2.0 (3)	C9—C8—N4—N5	0.8 (2)
N3—C7—C8—C9	176.40 (19)	C7—C8—N4—N5	−178.43 (17)
N4—C8—C9—N6	−1.0 (2)	C8—N4—N5—N6	−0.2 (2)
C7—C8—C9—N6	178.14 (19)	C8—C9—N6—N5	0.9 (2)
N4—C8—C9—C10	175.6 (2)	C10—C9—N6—N5	−176.1 (2)
C7—C8—C9—C10	−5.2 (4)	C8—C9—N6—C11	−177.44 (18)
C16—C11—C12—C13	−0.5 (3)	C10—C9—N6—C11	5.6 (3)
N6—C11—C12—C13	−176.89 (17)	N4—N5—N6—C9	−0.4 (2)
C11—C12—C13—C14	−0.1 (3)	N4—N5—N6—C11	178.13 (16)
C12—C13—C14—C15	−0.1 (3)	C12—C11—N6—C9	−136.0 (2)
C12—C13—C14—C17	−179.51 (19)	C16—C11—N6—C9	47.6 (3)
C13—C14—C15—C16	0.8 (3)	C12—C11—N6—N5	45.8 (2)
C17—C14—C15—C16	−179.7 (2)	C16—C11—N6—N5	−130.6 (2)
C12—C11—C16—C15	1.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2ⁱ	0.86	1.98	2.838 (2)	176
O2—H1O···O1ⁱⁱ	0.87 (4)	1.96 (4)	2.822 (2)	174 (3)
O2—H2O···N2ⁱ	0.79 (4)	2.43 (4)	2.966 (3)	126 (3)
O2—H2O···O1ⁱ	0.79 (4)	2.20 (4)	2.961 (2)	162 (3)

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

Footnotes

‡Additional corresponding author, e-mail: kariukib@cardiff.ac.uk.

Funding information

MHA thanks King Abdulaziz City for Science and Technology (KACST), Saudi Arabia for financial support (award No. 020-0180).

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