4′-(2-Meth­oxy­phen­yl)-2,2′:6′,2′′-terpyridine

Njogu, E.M.; Juma, D.O.; Zamisa, S.J.; Omondi, B.; Nyamori, V.O.

doi:10.1107/S241431462401143X

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 9| Part 11| November 2024| x241143

https://doi.org/10.1107/S241431462401143X

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4′-(2-Methoxyphenyl)-2,2′:6′,2′′-terpyridine

Eric M. Njogu,^a David O. Juma,^b ^* Sizwe J. Zamisa,^b Bernard Omondi ^b and Vincent O. Nyamori ^b

^aMultimedia University of Kenya, PO Box 15653-00503, Nairobi, Kenya, and ^bSchool of Chemistry and Physics, University of KwaZulu Natal, Private Bag X54001, Westville, Durban, 4000, South Africa
^*Correspondence e-mail: 224098093@stu.ukzn.ac.za

Edited by W. T. A. Harrison, University of Aberdeen, United Kingdom (Received 21 November 2024; accepted 25 November 2024; online 28 November 2024)

In the title compound, C₂₂H₁₇N₃O, the N atoms of the pyridine rings exhibit a typical trans–trans arrangement: the dihedral angles between the central pyridine ring and the peripheral rings are 22.24 (4) and 2.38 (4)°. In the crystal, pairwise C—H⋯N hydrogen bonds form inversion dimers described by an R²₂(6) graph set descriptor, which further interact through C—H⋯π and π–π interactions, creating a two-dimensional supramolecular network propagating in the bc plane.

Keywords: crystal structure; terpyridine.

CCDC reference: 2405021

Structure description

Terpyridines are N,N,N-type pincer ligands that provide tight chelation with various metal cations in a nearly planar cis–cis geometry of their pyridine N atoms (Wei et al., 2019 ). This conformation allows for a good conjugation between the aromatic rings and the metal cation making terpyridine a ‘non-innocent’ ligand, capable of stabilizing low-valency metal ions (García–Domínguez et al., 2017 ). The ligand exhibits two possible coordination modes: mono-terpyridine pincer complexes and bis-terpyridine complexes depending on the number of coordinating terpyridine ligands (Taniya et al., 2021 ). The transition-metal complexes of 4′-aryl-substituted-2,2′:6′,2"-terpyridines possess rich supramolecular chemistry (Wei et al., 2019) as well as biological, DNA binding, and electrochemical properties, which render them as useful candidates for applications in the ﬁelds of medicine and molecular biology (Lazić et al., 2016 ). The substituent groups on the ligands may be used to tailor the properties of the resulting coordination complexes (Shi et al., 2006 ).

The title compound, C₂₂H₁₇N₃O (I), is a terpyridine derivative with a 2-methoxyphenyl substituent at the third carbon atom of the central pyridine ring. The crystal structure of the compound contains one molecule in the asymmetric unit in space group P2₁/c. As is typical for a non-coordinated terpyridine, the structure exhibits a trans–trans arrangement of the pyridine N atoms [N1—C3—C4—N2 = 158.59 (10)°; N3—C17—C16—N2 = −179.09 (10)°], as illustrated in Fig. 1. The peripheral pyridine rings subtend dihedral angles of 22.24 (4)° (N1 ring) and 2.38 (4)° (N3 ring) with the central pyridine ring. The methoxyphenyl ring is significantly twisted away from the central pyridine ring, with a dihedral angle of 48.93 (4)°. All other geometrical parameters for (I) are comparable with those of 4′-(2,4-dimethoxyphenyl)-2,2′:6′,2′′-terpyridine (Cambridge Structural Database refcode: JEYHED; Demircioğlu et al., 2018 ).

Figure 1
The molecular structure of (I) showing displacement ellipsoids drawn at the 50% probability level.

In the extended structure of (I), weak C—H⋯N hydrogen bonds connect the molecules (Fig. 2, Table 1). These interactions form hydrogen-bonded cyclic dimers, described by an R₂²(6) graph set descriptor. The hydrogen-bonded dimers interact through C—H⋯π interactions, where C8—H8 interacts with the centroid of one of the peripheral pyridine rings and C13—H13 interacts with the centroid of the methoxy-substituted ring. These interactions link neighbouring dimers along the b-axis direction forming a zigzag pattern, as shown in Fig. 3. The planarity of the molecules facilitates π–π interactions between the central pyridine ring and the other pyridine ring not involved in the C—H⋯π intermolecular interaction, with the shortest centroid–centroid separation being 3.5864 (6) Å. The C—H⋯π and π–π interactions combine to form a two-dimensional supramolecular arrangement extending over the crystallographic bc plane.

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg4 are the centroids of the N1/C1–3/C14/C15 and C7–C12 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C21—H21⋯N3ⁱ	0.95	2.66	3.4138 (16)	137
C8—H8⋯Cg1ⁱⁱ	0.95	2.68	3.5698 (12)	155
C13—H13⋯Cg4ⁱⁱⁱ	0.95	2.77	3.5182 (12)	136
Symmetry codes: (i) ; (ii) ; (iii) $[x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Figure 2
Illustration of intermolecular C—H⋯N interactions in the extended structure of (I) depicted as blue dotted lines and C—H⋯π and π–π interactions represented by red dashed lines.

Figure 3
Representation of zigzag propagation patterns of the hydrogen bonded dimers along the crystallographic b-axis direction.

Synthesis and crystallization

The title compound was synthesized using a method modified from Winter et al. (2006 ): 2-methoxybenzaldehyde (10 mmol) was dissolved in ethanol (30 ml), cooled to 0 °C, and treated with a 2-acetylpyridine/NaOH solution. After stirring for 2 h at 0 °C, 25% aqueous ammonia (30 ml) was added, and the reaction was stirred at room temperature for 18 h. The precipitate was filtered, washed with water and 1:1 water–ethanol, dried under vacuum, and recrystallized from methanol solution to yield X-ray-quality crystals.

Refinement

Crystallographic data and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₂H₁₇N₃O
M_r	339.38
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	7.7366 (3), 29.5787 (10), 7.3852 (3)
β (°)	91.962 (2)
V (Å³)	1689.03 (11)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.08
Crystal size (mm)	0.43 × 0.28 × 0.26

Data collection
Diffractometer	Bruker SMART APEX2 area detector
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.955, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	36956, 4227, 3728
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.670

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.119, 1.03
No. of reflections	4227
No. of parameters	236
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.24
Computer programs: APEX2 and SAINT (Bruker, 2010 ), SHELXS (Sheldrick, 2008 ), SHELXL2019/3 (Sheldrick, 2015 ) and OLEX2 (Dolomanov et al., 2009 ).

Structural data

CCDC reference: 2405021

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S241431462401143X/hb4497sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S241431462401143X/hb4497Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S241431462401143X/hb4497Isup3.cml

checkCIF report

Computing details top

4'-(2-Methoxyphenyl)-2,2':6',2''-terpyridine top

Crystal data top

C₂₂H₁₇N₃O	F(000) = 712
M_r = 339.38	D_x = 1.335 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.7366 (3) Å	Cell parameters from 9871 reflections
b = 29.5787 (10) Å	θ = 2.6–28.4°
c = 7.3852 (3) Å	µ = 0.08 mm⁻¹
β = 91.962 (2)°	T = 100 K
V = 1689.03 (11) Å³	Block, yellow
Z = 4	0.43 × 0.28 × 0.26 mm

Data collection top

Bruker SMART APEX2 area detector diffractometer	4227 independent reflections
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs	3728 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
Detector resolution: 7.9 pixels mm^-1	θ_max = 28.4°, θ_min = 2.6°
ω and φ scans	h = −10→10
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −39→39
T_min = 0.955, T_max = 0.988	l = −9→9
36956 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.041	H-atom parameters constrained
wR(F²) = 0.119	w = 1/[σ²(F_o²) + (0.0697P)² + 0.611P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
4227 reflections	Δρ_max = 0.37 e Å⁻³
236 parameters	Δρ_min = −0.24 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.

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

	x	y	z	U_iso*/U_eq
O1	0.47285 (11)	0.30543 (3)	1.08916 (12)	0.02170 (19)
N1	0.14529 (13)	0.35669 (3)	0.52813 (13)	0.0196 (2)
N2	0.41380 (12)	0.44519 (3)	0.71159 (13)	0.01598 (19)
N3	0.78678 (13)	0.50369 (3)	0.89892 (14)	0.0217 (2)
C1	−0.12572 (16)	0.38731 (5)	0.41546 (18)	0.0264 (3)
H1	−0.231198	0.382780	0.348239	0.032*
C2	−0.00699 (16)	0.35250 (4)	0.43771 (17)	0.0235 (2)
H2	−0.035260	0.323951	0.385741	0.028*
C3	0.18315 (14)	0.39749 (4)	0.59943 (15)	0.0167 (2)
C4	0.35441 (14)	0.40258 (3)	0.69551 (14)	0.0158 (2)
C5	0.44371 (14)	0.36519 (3)	0.76556 (15)	0.0166 (2)
H5	0.397404	0.335618	0.750921	0.020*
C6	0.60216 (14)	0.37190 (3)	0.85748 (14)	0.0156 (2)
C7	0.70993 (14)	0.33454 (3)	0.93456 (14)	0.0158 (2)
C8	0.88534 (14)	0.33331 (4)	0.89734 (15)	0.0181 (2)
H8	0.932059	0.356180	0.823112	0.022*
C9	0.99367 (15)	0.29944 (4)	0.96611 (16)	0.0196 (2)
H9	1.112894	0.299176	0.939317	0.024*
C10	0.92535 (15)	0.26616 (4)	1.07407 (16)	0.0199 (2)
H10	0.997718	0.242459	1.119075	0.024*
C11	0.41225 (17)	0.27917 (5)	1.23632 (19)	0.0307 (3)
H11A	0.407983	0.247215	1.201421	0.046*
H11B	0.296187	0.289352	1.266515	0.046*
H11C	0.490993	0.282929	1.342035	0.046*
C12	0.64395 (14)	0.30124 (3)	1.04914 (15)	0.0169 (2)
C13	0.75168 (15)	0.26701 (4)	1.11749 (15)	0.0188 (2)
H13	0.706583	0.244292	1.193593	0.023*
C14	−0.08713 (16)	0.42885 (4)	0.49347 (18)	0.0252 (3)
H14	−0.166839	0.453225	0.483221	0.030*
C15	0.07000 (15)	0.43416 (4)	0.58670 (16)	0.0206 (2)
H15	0.100200	0.462304	0.641067	0.025*
C16	0.56678 (14)	0.45144 (3)	0.79773 (14)	0.0153 (2)
C17	0.63187 (14)	0.49871 (3)	0.81402 (14)	0.0155 (2)
C18	0.53607 (15)	0.53500 (4)	0.74648 (16)	0.0196 (2)
H18	0.427971	0.530273	0.684452	0.024*
C19	0.60155 (15)	0.57845 (4)	0.77145 (17)	0.0209 (2)
H19	0.538544	0.603934	0.727027	0.025*
C20	0.75910 (15)	0.58400 (4)	0.86153 (16)	0.0199 (2)
H20	0.805831	0.613325	0.882233	0.024*
C21	0.84764 (16)	0.54583 (4)	0.92113 (18)	0.0238 (3)
H21	0.957322	0.549703	0.980925	0.029*
C22	0.66411 (14)	0.41587 (4)	0.87251 (15)	0.0164 (2)
H22	0.772010	0.421713	0.933282	0.020*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0192 (4)	0.0219 (4)	0.0242 (4)	0.0007 (3)	0.0036 (3)	0.0082 (3)
N1	0.0222 (5)	0.0204 (5)	0.0163 (5)	−0.0044 (3)	0.0005 (4)	−0.0007 (3)
N2	0.0178 (4)	0.0157 (4)	0.0146 (4)	−0.0014 (3)	0.0013 (3)	0.0004 (3)
N3	0.0207 (5)	0.0164 (4)	0.0276 (5)	−0.0017 (3)	−0.0043 (4)	0.0011 (4)
C1	0.0196 (6)	0.0363 (7)	0.0230 (6)	−0.0054 (5)	−0.0042 (4)	0.0016 (5)
C2	0.0249 (6)	0.0264 (6)	0.0193 (6)	−0.0081 (4)	−0.0002 (4)	−0.0026 (4)
C3	0.0179 (5)	0.0180 (5)	0.0140 (5)	−0.0023 (4)	0.0008 (4)	0.0019 (4)
C4	0.0182 (5)	0.0156 (5)	0.0139 (5)	−0.0010 (4)	0.0015 (4)	−0.0004 (4)
C5	0.0196 (5)	0.0138 (5)	0.0163 (5)	−0.0016 (4)	0.0010 (4)	−0.0003 (4)
C6	0.0183 (5)	0.0144 (5)	0.0144 (5)	0.0012 (4)	0.0023 (4)	0.0008 (4)
C7	0.0195 (5)	0.0131 (4)	0.0147 (5)	0.0001 (4)	−0.0011 (4)	−0.0008 (4)
C8	0.0207 (5)	0.0169 (5)	0.0168 (5)	−0.0014 (4)	0.0008 (4)	−0.0001 (4)
C9	0.0185 (5)	0.0217 (5)	0.0186 (5)	0.0017 (4)	−0.0011 (4)	−0.0029 (4)
C10	0.0240 (5)	0.0178 (5)	0.0176 (5)	0.0041 (4)	−0.0035 (4)	−0.0014 (4)
C11	0.0263 (6)	0.0348 (7)	0.0315 (7)	0.0028 (5)	0.0078 (5)	0.0155 (5)
C12	0.0186 (5)	0.0162 (5)	0.0158 (5)	−0.0009 (4)	−0.0003 (4)	−0.0011 (4)
C13	0.0249 (5)	0.0157 (5)	0.0156 (5)	−0.0002 (4)	−0.0015 (4)	0.0021 (4)
C14	0.0200 (6)	0.0298 (6)	0.0255 (6)	0.0028 (4)	−0.0014 (5)	0.0035 (5)
C15	0.0205 (5)	0.0207 (5)	0.0205 (6)	−0.0007 (4)	−0.0007 (4)	0.0009 (4)
C16	0.0176 (5)	0.0139 (5)	0.0144 (5)	−0.0008 (4)	0.0020 (4)	0.0007 (4)
C17	0.0173 (5)	0.0148 (5)	0.0144 (5)	−0.0007 (4)	0.0018 (4)	0.0006 (4)
C18	0.0185 (5)	0.0169 (5)	0.0232 (6)	−0.0007 (4)	−0.0020 (4)	0.0029 (4)
C19	0.0231 (6)	0.0153 (5)	0.0246 (6)	0.0013 (4)	0.0020 (4)	0.0035 (4)
C20	0.0255 (6)	0.0147 (5)	0.0199 (6)	−0.0046 (4)	0.0043 (4)	−0.0008 (4)
C21	0.0226 (6)	0.0207 (6)	0.0277 (6)	−0.0043 (4)	−0.0054 (5)	0.0004 (4)
C22	0.0165 (5)	0.0161 (5)	0.0167 (5)	−0.0009 (4)	−0.0002 (4)	0.0010 (4)

Geometric parameters (Å, º) top

O1—C11	1.4279 (14)	C9—H9	0.9500
O1—C12	1.3718 (14)	C9—C10	1.3832 (17)
N1—C2	1.3400 (15)	C10—H10	0.9500
N1—C3	1.3449 (14)	C10—C13	1.3922 (16)
N2—C4	1.3454 (13)	C11—H11A	0.9800
N2—C16	1.3372 (14)	C11—H11B	0.9800
N3—C17	1.3415 (14)	C11—H11C	0.9800
N3—C21	1.3403 (14)	C12—C13	1.3949 (15)
C1—H1	0.9500	C13—H13	0.9500
C1—C2	1.3858 (18)	C14—H14	0.9500
C1—C14	1.3855 (18)	C14—C15	1.3854 (16)
C2—H2	0.9500	C15—H15	0.9500
C3—C4	1.4891 (15)	C16—C17	1.4896 (14)
C3—C15	1.3949 (15)	C16—C22	1.3965 (14)
C4—C5	1.3942 (15)	C17—C18	1.3874 (15)
C5—H5	0.9500	C18—H18	0.9500
C5—C6	1.3950 (15)	C18—C19	1.3915 (15)
C6—C7	1.4858 (14)	C19—H19	0.9500
C6—C22	1.3893 (14)	C19—C20	1.3783 (16)
C7—C8	1.3943 (15)	C20—H20	0.9500
C7—C12	1.4060 (15)	C20—C21	1.3848 (16)
C8—H8	0.9500	C21—H21	0.9500
C8—C9	1.3909 (15)	C22—H22	0.9500

C12—O1—C11	117.34 (9)	H11A—C11—H11B	109.5
C2—N1—C3	117.01 (10)	H11A—C11—H11C	109.5
C16—N2—C4	117.74 (9)	H11B—C11—H11C	109.5
C21—N3—C17	117.64 (10)	O1—C12—C7	116.06 (9)
C2—C1—H1	120.8	O1—C12—C13	123.82 (10)
C14—C1—H1	120.8	C13—C12—C7	120.11 (10)
C14—C1—C2	118.50 (11)	C10—C13—C12	119.95 (10)
N1—C2—C1	123.94 (11)	C10—C13—H13	120.0
N1—C2—H2	118.0	C12—C13—H13	120.0
C1—C2—H2	118.0	C1—C14—H14	120.7
N1—C3—C4	117.10 (9)	C15—C14—C1	118.69 (11)
N1—C3—C15	122.92 (10)	C15—C14—H14	120.7
C15—C3—C4	119.97 (10)	C3—C15—H15	120.5
N2—C4—C3	115.62 (9)	C14—C15—C3	118.91 (11)
N2—C4—C5	123.16 (10)	C14—C15—H15	120.5
C5—C4—C3	121.21 (9)	N2—C16—C17	117.35 (9)
C4—C5—H5	120.5	N2—C16—C22	122.72 (9)
C4—C5—C6	118.93 (9)	C22—C16—C17	119.93 (10)
C6—C5—H5	120.5	N3—C17—C16	115.79 (9)
C5—C6—C7	123.57 (9)	N3—C17—C18	122.73 (10)
C22—C6—C5	117.84 (9)	C18—C17—C16	121.48 (10)
C22—C6—C7	118.56 (9)	C17—C18—H18	120.7
C8—C7—C6	118.76 (9)	C17—C18—C19	118.64 (10)
C8—C7—C12	118.43 (10)	C19—C18—H18	120.7
C12—C7—C6	122.76 (10)	C18—C19—H19	120.5
C7—C8—H8	119.2	C20—C19—C18	119.08 (10)
C9—C8—C7	121.69 (10)	C20—C19—H19	120.5
C9—C8—H8	119.2	C19—C20—H20	120.8
C8—C9—H9	120.5	C19—C20—C21	118.42 (10)
C10—C9—C8	119.06 (11)	C21—C20—H20	120.8
C10—C9—H9	120.5	N3—C21—C20	123.46 (11)
C9—C10—H10	119.6	N3—C21—H21	118.3
C9—C10—C13	120.71 (10)	C20—C21—H21	118.3
C13—C10—H10	119.6	C6—C22—C16	119.59 (10)
O1—C11—H11A	109.5	C6—C22—H22	120.2
O1—C11—H11B	109.5	C16—C22—H22	120.2
O1—C11—H11C	109.5

O1—C12—C13—C10	−178.02 (10)	C7—C8—C9—C10	0.04 (17)
N1—C3—C4—N2	158.59 (10)	C7—C12—C13—C10	0.84 (16)
N1—C3—C4—C5	−22.36 (15)	C8—C7—C12—O1	176.60 (9)
N1—C3—C15—C14	−1.38 (17)	C8—C7—C12—C13	−2.34 (16)
N2—C4—C5—C6	0.20 (17)	C8—C9—C10—C13	−1.61 (17)
N2—C16—C17—N3	−179.09 (10)	C9—C10—C13—C12	1.18 (17)
N2—C16—C17—C18	1.50 (16)	C11—O1—C12—C7	−165.58 (11)
N2—C16—C22—C6	0.33 (16)	C11—O1—C12—C13	13.32 (16)
N3—C17—C18—C19	−1.50 (18)	C12—C7—C8—C9	1.92 (16)
C1—C14—C15—C3	−0.31 (18)	C14—C1—C2—N1	−1.13 (19)
C2—N1—C3—C4	−178.33 (10)	C15—C3—C4—N2	−21.48 (15)
C2—N1—C3—C15	1.75 (16)	C15—C3—C4—C5	157.57 (11)
C2—C1—C14—C15	1.48 (18)	C16—N2—C4—C3	179.67 (9)
C3—N1—C2—C1	−0.47 (17)	C16—N2—C4—C5	0.65 (16)
C3—C4—C5—C6	−178.77 (10)	C16—C17—C18—C19	177.86 (10)
C4—N2—C16—C17	179.69 (9)	C17—N3—C21—C20	0.10 (19)
C4—N2—C16—C22	−0.92 (16)	C17—C16—C22—C6	179.71 (10)
C4—C3—C15—C14	178.70 (10)	C17—C18—C19—C20	0.23 (17)
C4—C5—C6—C7	−178.80 (10)	C18—C19—C20—C21	1.09 (17)
C4—C5—C6—C22	−0.78 (16)	C19—C20—C21—N3	−1.31 (19)
C5—C6—C7—C8	131.01 (11)	C21—N3—C17—C16	−178.07 (10)
C5—C6—C7—C12	−51.41 (16)	C21—N3—C17—C18	1.33 (17)
C5—C6—C22—C16	0.53 (16)	C22—C6—C7—C8	−46.99 (14)
C6—C7—C8—C9	179.61 (10)	C22—C6—C7—C12	130.59 (11)
C6—C7—C12—O1	−0.99 (15)	C22—C16—C17—N3	1.50 (15)
C6—C7—C12—C13	−179.93 (10)	C22—C16—C17—C18	−177.91 (10)
C7—C6—C22—C16	178.65 (10)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg4 are the centroids of the N1/C1–3/C14/C15 and C7–C12 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21···N3ⁱ	0.95	2.66	3.4138 (16)	137
C8—H8···Cg1ⁱⁱ	0.95	2.68	3.5698 (12)	155
C13—H13···Cg4ⁱⁱⁱ	0.95	2.77	3.5182 (12)	136

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

Acknowledgements

The authors thank the University of KwaZulu Natal for provision of research facilities.

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