Crystal structure and Hirshfeld surface analysis of the coordination compound di­aqua­[5,10,15,20-tetra­kis­(4-chloro­phen­yl)porphyrinato-κ4N]magnesium(II)

Alamri, M.A.

doi:10.1107/S2056989026000836

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ISSN: 2056-9890

Volume 82| Part 3| March 2026| Pages 249-253

https://doi.org/10.1107/S2056989026000836

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Crystal structure and Hirshfeld surface analysis of the coordination compound diaqua[5,10,15,20-tetrakis(4-chlorophenyl)porphyrinato-κ⁴N]magnesium(II)

Mona A. Alamri ^a ^*

^aDepartment of Chemistry, College of Science, Qassim University, Buraidah 52571, Saudi Arabia
^*Correspondence e-mail: [email protected]

Edited by B. Therrien, University of Neuchâtel, Switzerland (Received 5 January 2026; accepted 27 January 2026; online 5 February 2026)

During the synthesis of the (oxalato)[5,10,15,20-tetrakis(4-chlorophenyl)porphyrinato]magnesium(II) ([Mg(TClPP)(ox)]) complex [TClPP = 5,10,15,20-tetrakis(4-chlorophenyl)porphyrinate and ox = oxalate], the title compound, [Mg(C₄₄H₂₄ClMgN₄O₂)(H₂O)₂] ([Mg(TClPP)(H₂O)₂]), was obtained as a by-product. The diaqua–Mg^II porphyrin complex crystallizes in the I4/m space group. In the asymmetric unit, except for two carbon atoms of the phenyl ring, all atoms lie on special positions. In the crystal, the [Mg(TClPP)(H₂O)₂] molecules form layers parallel to the a axis. The crystal packing features C—H⋯π interactions involving the pyrrole rings and non-conventional O—H⋯Cl hydrogen bonds between the oxygen atom of the water axial ligands and the chloride of neighboring phenyl groups. Hirshfeld surface analysis indicates that intermolecular contacts are dominated by H⋯H (50.2%), followed by H⋯Cl (21.6%) and H⋯C (21.2%) interactions, then by less chemically meaningful C⋯Cl (6.0%) contacts.

Keywords: crystal structure; magnesium(II) porphyrin; diaqua complex; intermolecular interactions; Hirshfeld analysis.

CCDC reference: 2526366

1. Chemical context

Magnesium, the eighth most abundant element in the Earth's crust and an essential nutrient for all living organisms, plays a central role in biological processes, most notably as the coordinating metal ion in chlorophyll, the photosynthetic pigment that sustains life on Earth (Barker & Pilbeam, 2015 ). The coordination chemistry of magnesium(II), particularly within porphyrin frameworks, has thus attracted sustained scientific interest due to its fundamental relevance to photosynthesis and its potential in bioinspired technologies (Borah & Bhuyan, 2017 ).

The foundation of magnesium(II) metalloporphyrin chemistry was laid in the early to mid-20th century. One of the pioneering contributions came from Hans Fischer, whose extensive work on porphyrin synthesis and metal insertion in the 1930s and 1940s provided the first systematic routes to metalloporphyrins, although Mg^II complexes were often challenging to isolate due to their lability in protic media (Fischer et al., 1937 ). Later, the structural elucidation of chlorophyll by Robert Burns Woodward and colleagues in the 1960s, culminating in the total synthesis of chlorophyll a offered profound insight into the unique coordination environment of Mg^II in natural porphyrinoids, notably the presence of a fifth and sixth axial ligands and the susceptibility of the Mg—N bonds to hydrolysis (Woodward et al., 1960 ).

Unlike transition metals that form robust metalloporphyrins, Mg^II porphyrins are diamagnetic, d⁰ complexes with labile axial coordination sites, which imparts distinctive photophysical properties, but also presents synthetic challenges. Nevertheless, these attributes make Mg^II porphyrins particularly attractive for applications that require efficient light harvesting, energy transfer, and reversible ligand binding, all hallmarks of natural photosynthetic systems.

In recent years, synthetic Mg^II porphyrins have found utility beyond biology. They serve as key components in artificial photosynthetic devices, where they act as light absorbers and electron donors in photoinduced charge-separation systems (Gust et al., 2001 ). For instance, several reported investigations have engineered tailored Mg porphyrins for integration into molecular triads and tetrads that mimic the primary events of photosynthesis, achieving long-lived charge-separated states relevant to solar energy conversion (Borah et al., 2017 ). Additionally, Mg^II porphyrins have been employed as sensors (Gutiérrez et al., 2014 ). More recently, they have been explored in photocatalysts for the transformation of CO₂ to cyclic carbonates and oxazolidinones (Meher et al., 2024 ).

Accordingly, the controlled synthesis, stabilization, and functionalization of Mg^II porphyrins remain active areas of research, driven by both fundamental curiosity and the pursuit of sustainable technologies inspired by nature's design. Herein we report the synthesis, the single crystal X-ray molecular structure and the Hirshfeld surfaces analysis of the title diaqua[{5,10,15,20-tetrakis(4-chlorophenyl)}porphyrinato-κ⁴N]magnesium(II) coordination compound.

2. Structural commentary

The title compound crystallizes in the tetragonal space group I4/m (Fig. 1). The asymmetric unit comprises one quarter of the [Mg(TClPP)(H₂O)₂] molecule leading to the formula [Mg(C₄₄H₂₄ClMgN₄O₂)(H₂O)₂]. The central Mg^II ion is coordinated to nitrogen atoms of the porphyrin core, and to oxygen atoms of the water molecules, thus showing an octahedral geometry.

Figure 1
[Mg(TClPP)(H₂O)₂] showing the atom labelling scheme. Displacement ellipsoids are drawn at the 40% probability level. All possible positions of the disordered H atoms of the water molecules are shown.

The Mg—O(H₂O) distance of the [Mg(TClPP)(H₂O)₂] complex is 2.248 (3) Å, which is in the normal range of bis(aqua)–porphyrin complexes, e.g., for the related [Mg(TBrPP)(H₂O)₂] (TBrP = 5,10,15,20-tetrakis(4-bromophenyl)porphyrinate), the Mg—O(H₂O) bond length is 2.221 (4) Å (Amiri et al., 2015 ). Notably, the [Mg(TBrPP)(H₂O)₂] related species is isotypic to our TClPP–magnesium-diaqua complex. In 2022, the structure of the [Mg(TClPP)(pyz)][Mg(TClPP)(H₂O)₂] (pyz = pyrazine) complex was reported, for which [Mg(TClPP)(pyz)] and [Mg(TClPP)(H₂O)₂] are present in the same asymmetric unit (PELVUB; Singh et al., 2022 ). For this [Mg(TClPP)(H₂O)₂] coordination compound, the Mg—O(H₂O) distance is 2.267 (5) Å, which is slightly longer than that of the title compound.

For the pentacoordinated monaqua–Mg^II–porphyrin complex [Mg(Porph)(H₂O)] (Porph = meso-arylporphyrinate), the Mg—O(H₂O) bond length is shorter than those of the bisaqua magnesium(II) porphyrins such as the [Mg(TPP)(H₂O)₂] complex, for which Mg—O(H₂O) is 2.053 (5) Å (McKee & Rodley, 1988 ). The distance between the central Mg²⁺ ion and the N1 atom of the TClPP porphyrinate of [Mg(TClPP)(H₂O)₂] (Mg—N_p) is 2.0646 (17) Å. For the related complexes [Mg(TBrPP)(H₂O)₂] (Amiri et al., 2015) and [Mg(TClPP)(H₂O)₂] (Singh et al., 2022), the average distances between the central Mg²⁺ ion and the four nitrogen atoms of the pyrrole rings of the porphyrin macrocycle (Mg—Np) are 2.069 and 2.082 Å, respectively. All these Mg—Np values are typical of magnesium(II) metalloporphyrins (Jabli et al., 2022 ).

3. Supramolecular features

In the crystal, the [Mg(TClPP)(H₂O)₂] complex molecules form layers parallel to the [100] direction (Fig. 2). As shown in Fig. 3, each oxygen atom of the two trans axial aqua ligands and the four symmetry-related atoms are involved in hydrogen bonds with the chlorine atom of a neighboring TClPP porphyrinate molecule with a distance of 3.691 (2) Å (Table 1). The crystal of the new Mg^II–diaqua–TClPP metalloporphyrin is further consolidated by C—H⋯π interactions between the carbon C7 of a phenyl of a TClPP porphyrinate and the centroid of the pyrrole rings of the porphyrin core with a C7⋯centroid distance of 3.608 (2) Å (Fig. 3., Table 1).

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the N1,C1,C2,C9′′,C5′′ and C5,C9,C2′,C1′,N1′ rings, respectively. Symmetry codes: (′) −y, −1 + x, z; (′′) 1 + y, −x, z.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯Cg1ⁱ	0.95	2.75	3.608 (2)	150
C7—H7⋯Cg2ⁱⁱ	0.95	2.75	3.608 (2)	150
O1—H10⋯Cl1ⁱⁱⁱ	1.01	2.92	3.691 (2)	128
Symmetry codes: (i) $[y+{\script{1\over 2}}, -x+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, -y-{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, y-{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Figure 2
Packing viewed along the [100] direction showing the layers made by [Mg(TClPP)(H₂O)₂] complex molecules.

Figure 3
View showing the C—H⋯Cl and the C—H⋯Cg (Cg is the centroid of a pyrrol ring) intermolecular interactions.

4. Database survey

A survey of the Cambridge Structural Database (CSD, version 6.00, update April 2025; Groom et al., 2016 ) revealed 11 structures of aqua magnesium(II) porphyrin complexes. Among these porphyrinic coordination complexes, four are hexacoordinated diaqua complexes and seven are pentacoordinated monoaqua metalloporphyrins. The four reported diaqua–Mg^II–porphyrin complexes are: [Mg(T3,5-OMePP)(H₂O)₂] (T3,5-OMePP = 5,10,15,20-tetrakis(3,5-dimethoxyphenyl)porphyrinate) (GOJGEV; Borah et al., 2024 ), [Mg(TBPP)(H₂O)₂] (TPBPP = 5,10,15,20-tetrakis(4-(benzoyloxy)phenyl)porphyrinate) (CUCZAD; Amiri et al., 2015), [Mg(TPP)(H₂O)₂](18-C-6) (TPP = 5,10,15,20-tetraphenylporphyrinate and 18-C-6 = 18-crown-6) (LERTAF; Ezzayani et al., 2013 ) and [MgTClPP(pyz)₂][MgTClPP(H₂O)₂] (pyz = pyrazine) (PELVUB; Singh et al., 2022). In this latter example, one half [Mg(TClPP)(pyz)₂] molecule and one half [Mg(TClPP)(H₂O)₂] molecule are both present in the asymmetric unit. The seven reported monoaqua Mg^II metalloporphyrins are: [Mg(TPP)(H₂O)]·2(C₆H₇N) (C₆H₇N = picoline) (DUJKUO; Ong et al., 1986 ), [Mg(TPP)(H₂O)]·C₃H₆O (GEPBUY; McKee & Rodley, 1988), [Mg(T3,5-OMePP)(H₂O)] (GUHXAL; Borah et al., 2017), [Mg(TPBP)(H₂O)] (TPBP = 5,10,15,20-tetrakis(4-(benzoyloxy)phenyl)porphyrinate (HALDOR; Amiri et al., 2022 ), [Mg(TMPP)(H₂O)] (TMPP = 5,10,15,20-tetrakis(4-methoxyphenyl)porphyrinate) (JONKAY; Yang et al., 1991 ), [Mg(TPP)(H₂O)] (MGPPOR; Timkovich et al., 1969 ), and [Mg(TTP)(H₂O)] (TTP = 5,10,15,20-tetrakis(4-methylphenyl)porphyrinate) (YONYAF; Meher et al., 2024).

5. Hirshfeld surface analysis

The intermolecular interactions responsible for the crystal cohesion of [Mg(TClPP)(H₂O)₂] were also investigated using Hirshfeld surface analysis and two-dimensional fingerprint plots (Turner et al., 2017 ). The Hirshfeld surfaces were obtained using a standard high surface resolution, mapped over d_norm (Fig. 4). As shown in Fig. 4, the red spots correspond to the non-conventional O—H⋯Cl interactions between the water oxygen atom and the chlorine atoms in the para-positions of the four TClPP phenyl rings of neighboring [Mg(TClPP)(H₂O)₂] molecules. Similarly, the C7—H7⋯π interactions (Table 1) are represented as red dots. The d_i versus d_e plots shown in Fig. 5 illustrate the distribution of individual intermolecular interactions on the basis of fingerprint maps. The crystal structure is dominated by H⋯H (50.2%) interactions, followed by H⋯Cl/Cl⋯H (21.6%), H⋯C/C⋯H (21.2%) and C⋯Cl/Cl⋯C (6.0) contacts.

Figure 4
Hirshfeld surface plotted over d_norm for the title compound.

Figure 5
Two-dimensional fingerprint plots showing the distribution of intermolecular interactions responsible for the cohesion of the title complex.

6. Synthesis and crystallization of the title complex

In order to prepare the [Mg(TClPP)(ox)] complex (ox = oxalato C₂O₄²⁻), a solution of [Mg(TClPP)] (100 mg, 0.128 mmol) in dichloromethane (40 mL) was added an excess of 18-crown-6 ether (250 mg, 0.946 mmol) and a large excess of K₂C₂O₄·H₂O (potassium oxalate monohydrate) (30 mg, 0.163 mol). The reaction mixture was stirred at room temperature for three h and at the end of the reaction, the color of the solution gradually changed from purple to blue. The resulting material was crystallized by diffusion of n-hexane through the dichloromethane solution. Single-crystal X-ray diffraction revealed that the crystals obtained correspond to the diaqua–magnesium(II)-TClPP coordination compound. Elemental analysis calculated (%) for C₄₄H₂₈ClMgN₄O₂ (M_W = 810.83), C 65.18, H 3.48, N 6.91; found: C 65.49, H 3.61, N 7.12.

7. Refinement

Crystal data, data collection and structure refinement details are given in Table 2. The H-atom position of the axially bonded aqua ligand was found in difference maps and then refined with U_iso(H) = 1.5U_eq(O). The molecular symmetry of the water molecule is not compatible with the fourfold axis; hence, the occupancy of this H atom was fixed to 0.5. The H atoms attached to C atoms were fixed geometrically and treated as riding with C—H = 0.95 Å and U_iso(H) = 1.5U_eq(C).

Table 2
Experimental details

Crystal data
Chemical formula	[Mg(C₄₄H₂₄Cl₄N₄)(H₂O)₂]
M_r	810.81
Crystal system, space group	Tetragonal, I4/m
Temperature (K)	200
a, c (Å)	14.605 (2), 9.4397 (19)
V (Å³)	2013.5 (7)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.35
Crystal size (mm)	0.30 × 0.30 × 0.30

Data collection
Diffractometer	Bruker AXS Enraf–Nonius Kappa APEXII
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.711, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	8146, 1216, 1078
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.115, 1.07
No. of reflections	1216
No. of parameters	78
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.41
Computer programs: APEX2 and SAINT (Bruker, 2014 ), SIR2004 (Burla et al., 2005 ) and SHELXL2015 (Sheldrick, 2015 ).

Supporting information

CCDC reference: 2526366

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989026000836/tx2107sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989026000836/tx2107Isup3.hkl

checkCIF report

Computing details top

Diaqua[5,10,15,20-tetrakis(4-chlorophenyl)porphyrinato-κ⁴N]magnesium(II) top

Crystal data top

[Mg(C₄₄H₂₄Cl₄N₄)(H₂O)₂]	D_x = 1.337 Mg m⁻³
M_r = 810.81	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I4/m	Cell parameters from 8167 reflections
a = 14.605 (2) Å	θ = 2.6–27.5°
c = 9.4397 (19) Å	µ = 0.35 mm⁻¹
V = 2013.5 (7) Å³	T = 200 K
Z = 2	Block, blue
F(000) = 832	0.30 × 0.30 × 0.30 mm

Data collection top

Bruker AXS Enraf–Nonius Kappa APEXII diffractometer	1078 reflections with I > 2σ(I)
Radiation source: Incoatec ISG250	R_int = 0.032
φ and ω scans	θ_max = 27.5°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −18→18
T_min = 0.711, T_max = 1	k = −17→18
8146 measured reflections	l = −9→12
1216 independent reflections

Refinement top

Refinement on F²	1 restraint
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.041	H-atom parameters constrained
wR(F²) = 0.115	w = 1/[σ²(F_o²) + (0.056P)² + 1.969P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
1216 reflections	Δρ_max = 0.32 e Å⁻³
78 parameters	Δρ_min = −0.41 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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Mg1	0.5000	−0.5000	0.0000	0.0360 (4)
N1	0.53951 (11)	−0.36427 (11)	0.0000	0.0283 (4)
C4	0.33650 (13)	−0.20277 (14)	0.0000	0.0290 (4)
C1	0.48278 (14)	−0.28960 (13)	0.0000	0.0278 (4)
C5	0.33189 (14)	−0.37233 (14)	0.0000	0.0286 (4)
C3	0.38633 (13)	−0.29286 (13)	0.0000	0.0275 (4)
C8	0.24114 (15)	−0.03956 (14)	0.0000	0.0370 (5)
C6	0.31214 (13)	−0.16133 (12)	0.1253 (2)	0.0463 (5)
H6	0.3285	−0.1893	0.2126	0.056*
O1	0.5000	−0.5000	0.2381 (3)	0.0583 (7)
H10	0.5516	−0.5286	0.2938	0.070*	0.5
C7	0.26386 (14)	−0.07894 (12)	0.1262 (2)	0.0503 (5)
H7	0.2471	−0.0508	0.2131	0.060*
Cl1	0.17689 (4)	0.06145 (4)	0.0000	0.0588 (3)
C2	0.53683 (15)	−0.20673 (14)	0.0000	0.0320 (5)
H2	0.5142	−0.1457	0.0000	0.038*
C9	0.23260 (14)	−0.37383 (14)	0.0000	0.0311 (4)
H9	0.1931	−0.3221	0.0000	0.037*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mg1	0.0233 (4)	0.0233 (4)	0.0615 (10)	0.000	0.000	0.000
N1	0.0240 (8)	0.0228 (8)	0.0381 (10)	−0.0006 (6)	0.000	0.000
C4	0.0270 (9)	0.0245 (9)	0.0354 (11)	0.0016 (7)	0.000	0.000
C1	0.0295 (10)	0.0232 (9)	0.0307 (10)	0.0003 (7)	0.000	0.000
C5	0.0262 (9)	0.0271 (9)	0.0326 (10)	0.0032 (7)	0.000	0.000
C3	0.0277 (9)	0.0246 (9)	0.0303 (10)	0.0036 (7)	0.000	0.000
C8	0.0268 (10)	0.0232 (9)	0.0609 (15)	0.0026 (8)	0.000	0.000
C6	0.0605 (11)	0.0423 (9)	0.0361 (9)	0.0202 (8)	−0.0061 (8)	−0.0041 (7)
O1	0.0619 (10)	0.0619 (10)	0.0510 (16)	0.000	0.000	0.000
C7	0.0599 (11)	0.0429 (9)	0.0481 (11)	0.0190 (8)	−0.0033 (9)	−0.0148 (8)
Cl1	0.0414 (4)	0.0271 (3)	0.1078 (7)	0.0095 (2)	0.000	0.000
C2	0.0349 (10)	0.0218 (9)	0.0393 (11)	−0.0021 (8)	0.000	0.000
C9	0.0246 (9)	0.0310 (10)	0.0377 (11)	0.0050 (8)	0.000	0.000

Geometric parameters (Å, º) top

Mg1—N1ⁱ	2.0646 (17)	C5—C3	1.407 (3)
Mg1—N1ⁱⁱ	2.0646 (17)	C5—C9	1.450 (3)
Mg1—N1ⁱⁱⁱ	2.0646 (17)	C8—C7	1.364 (2)
Mg1—N1	2.0646 (17)	C8—C7^iv	1.364 (2)
Mg1—O1ⁱ	2.248 (3)	C8—Cl1	1.748 (2)
Mg1—O1	2.248 (3)	C6—C7	1.395 (2)
N1—C1	1.370 (3)	C6—H6	0.9500
N1—C5ⁱⁱ	1.372 (3)	O1—H10	1.0100
C4—C6^iv	1.376 (2)	C7—H7	0.9500
C4—C6	1.376 (2)	C2—C9ⁱⁱ	1.358 (3)
C4—C3	1.504 (3)	C2—H2	0.9500
C1—C3	1.409 (3)	C9—C2ⁱⁱⁱ	1.358 (3)
C1—C2	1.445 (3)	C9—H9	0.9500
C5—N1ⁱⁱⁱ	1.372 (3)

N1ⁱ—Mg1—N1ⁱⁱ	90.0	C3—C1—C2	125.05 (19)
N1ⁱ—Mg1—N1ⁱⁱⁱ	90.0	N1ⁱⁱⁱ—C5—C3	125.41 (18)
N1ⁱⁱ—Mg1—N1ⁱⁱⁱ	180.00 (9)	N1ⁱⁱⁱ—C5—C9	109.30 (17)
N1ⁱ—Mg1—N1	180.0	C3—C5—C9	125.28 (18)
N1ⁱⁱ—Mg1—N1	89.999 (1)	C5—C3—C1	126.35 (18)
N1ⁱⁱⁱ—Mg1—N1	90.001 (1)	C5—C3—C4	116.63 (17)
N1ⁱ—Mg1—O1ⁱ	90.0	C1—C3—C4	117.01 (17)
N1ⁱⁱ—Mg1—O1ⁱ	90.0	C7—C8—C7^iv	121.7 (2)
N1ⁱⁱⁱ—Mg1—O1ⁱ	90.0	C7—C8—Cl1	119.11 (10)
N1—Mg1—O1ⁱ	90.0	C7^iv—C8—Cl1	119.11 (10)
N1ⁱ—Mg1—O1	90.0	C4—C6—C7	121.01 (17)
N1ⁱⁱ—Mg1—O1	90.0	C4—C6—H6	119.5
N1ⁱⁱⁱ—Mg1—O1	90.0	C7—C6—H6	119.5
N1—Mg1—O1	90.0	Mg1—O1—H10	121.4
O1ⁱ—Mg1—O1	180.0	C8—C7—C6	118.81 (17)
C1—N1—C5ⁱⁱ	107.05 (16)	C8—C7—H7	120.6
C1—N1—Mg1	126.55 (13)	C6—C7—H7	120.6
C5ⁱⁱ—N1—Mg1	126.40 (14)	C9ⁱⁱ—C2—C1	106.96 (18)
C6^iv—C4—C6	118.6 (2)	C9ⁱⁱ—C2—H2	126.5
C6^iv—C4—C3	120.67 (10)	C1—C2—H2	126.5
C6—C4—C3	120.67 (10)	C2ⁱⁱⁱ—C9—C5	107.02 (18)
N1—C1—C3	125.28 (18)	C2ⁱⁱⁱ—C9—H9	126.5
N1—C1—C2	109.67 (18)	C5—C9—H9	126.5

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

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the N1,C1,C2,C9'',C5'' and C5,C9,C2',C1',N1' rings, respectively. Symmetry codes: (') -y, -1 + x, z; ('') 1 + y, -x, z.

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···Cg1^v	0.95	2.75	3.608 (2)	150
C7—H7···Cg2^vi	0.95	2.75	3.608 (2)	150
O1—H10···Cl1^vii	1.01	2.92	3.691 (2)	128

Symmetry codes: (v) y+1/2, −x+1/2, z+1/2; (vi) −x+1/2, −y−1/2, z+1/2; (vii) x+1/2, y−1/2, z+1/2.

Acknowledgements

The researcher would like to thank the Deanship of Graduate Studies and Scientific Research at Qassim University for financial support (QU-APC-2026).

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