Chlorido­(2-{(2-hy­droxy­eth­yl)[tris­(hy­droxy­meth­yl)meth­yl]amino}­ethano­lato-κ5N,O,O′,O′′,O′′′)copper(II)

Fortis-Valera, M.; Arroyo-Carmona, R.E.; Pérez-Benítez, A.; Bernès, S.

doi:10.1107/S2414314624004395

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 9| Part 5| May 2024| x240439

https://doi.org/10.1107/S2414314624004395

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Chlorido(2-{(2-hydroxyethyl)[tris(hydroxymethyl)methyl]amino}ethanolato-κ⁵N,O,O′,O′′,O′′′)copper(II)

Monserrat Fortis-Valera,^a Rosa Elena Arroyo-Carmona,^a Aarón Pérez-Benítez ^a and Sylvain Bernès ^b ^*

^aFacultad de Ciencias Químicas, Benemérita Universidad Autónoma de Puebla, Ciudad Universitaria, 72570 Puebla, Pue., Mexico, and ^bInstituto de Física, Benemérita Universidad Autónoma de Puebla, Av. San Claudio y 18 Sur, 72570 Puebla, Pue., Mexico
^*Correspondence e-mail: sylvain_bernes@hotmail.com

Edited by M. Weil, Vienna University of Technology, Austria (Received 25 April 2024; accepted 10 May 2024; online 24 May 2024)

The title complex, [Cu(C₈H₁₈NO₅)Cl] or [Cu(H₄bis-tris)Cl], was obtained starting from the previously reported [Cu(H₅bis-tris)Cl]Cl compound. The deprotonation of the aminopolyol ligand H₅bis-tris {[bis(2-hydroxyethyl)amino]tris(hydroxymethyl)methane, C₈H₁₉NO₅} promotes the formation of a very strong O—H⋯O intermolecular hydrogen bond, characterized by an H⋯O separation of 1.553 (19) Å and an O—H⋯O angle of 178 (4)°. The remaining hydroxy groups are also engaged in hydrogen bonds, forming R₂²(8), R₄⁴(16), R₄⁴(20) and R₄⁴(22) ring motifs, which stabilize the triperiodic supramolecular network.

Keywords: crystal structure; coordination compound; bis-tris; supramolecular structure; very strong hydrogen bonds.

CCDC reference: 2355145

Structure description

Aminopolyol [bis(2-hydroxyethyl)amino]tris(hydroxymethyl)methane, generally abbreviated H₅bis-tris, is able to coordinate first-row late transition metals and lanthanides (Nicholson et al., 2001 ). This molecule behaves systematically as a chelating pentadentate ligand, through the tertiary N atom and four of the five alcohol arms. The metal coordination sphere is then completed with an ancillary ligand, frequently an aqua or a chlorido ligand. Furthermore, depending on the reaction conditions, H₅bis-tris can be deprotonated, affording chelating anions. While anions (H_5–nbis-tris)ⁿ⁻ with n = 2 to 4 have been determined by X-ray structure analysis in several compounds (e.g. Stamatatos et al., 2009 ), it seems that to date the anionic ligand with n = 1, (H₄bis-tris)⁻, has been observed only once: Kirillova et al. (2017 ) reported a crystal structure comprising [Cu(H₅bis-tris)(inic)]⁺ and [Cu(H₄bis-tris)(inic)] entities, where inic stands for the isonicotinate anion. We now report the structure of the second complex where (H₄bis-tris)⁻ acts as a ligand, namely [Cu(H₄bis-tris)Cl], which was obtained serendipitously from [Cu(H₅bis-tris)Cl]⁺Cl (Inomata et al., 2004 ).

The new Cu^II molecular complex displays the expected distorted octahedral shape (Fig. 1). Since all H atoms could be located from electron-difference maps, the deprotonated alcohol group was clearly identified as being O5. Moreover, the anion formula for (H₄bis-tris)⁻ is consistent with the charge balance in the complex. The tetragonal distortion resulting from the Jahn–Teller effect for Cu^II increases bond lengths Cu1—O3 and Cu1—O4 [2.361 (3) and 2.436 (2) Å] in comparison with bond lengths in the equatorial plane N1/O2/O5/Cl1 [1.943 (2) to 2.2812 (10) Å]. The shape of the neutral molecule [Cu(H₄bis-tris)Cl] is actually close to that observed for the cation [Cu(H₅bis-tris)Cl]⁺: a molecular overlay gives a root-mean-square (r.m.s.) deviation of 0.28 Å and a maximum deviation of 0.91 Å (Fig. 1, inset).

Figure 1
Molecular structure of the title compound, with displacement ellipsoids for non-H atoms at the 60% probability level. The inset is an overlay calculated with Mercury (Macrae et al., 2020

), comparing the shape of [Cu(H₅bis-tris)Cl]⁺ (blue) and the title complex [Cu(H₄bis-tris)Cl] (red). The crystal structure of [Cu(H₅bis-tris)Cl]Cl has been published (Inomata et al., 2004

; CCDC refcode FIPRAY); however, the authors did not deposit a CIF file at that time. A CSD communication for this compound was thus used for the fit (FIPRAY01; Fortis-Valera et al., 2018

The space group and the network of hydrogen bonds are however modified upon deprotonation of H₅bis-tris. In the new complex, all hydroxy groups are donors for hydrogen bonding, and the deprotonated hydroxy group, O5, is an acceptor (Table 1). The latter is engaged in the strongest interaction, O2—H2⋯O5, with a very short H2⋯O5 distance of 1.553 (19) Å and with an angle O2—H2⋯O5 = 178 (4)°. Indeed, only few shorter intermolecular H⋯O separations can be retrieved from the Cambridge Structural Database (CSD v. 5.45, updated March 2024; Groom et al., 2016 ) for CH₂—CH₂—O⋯H—O fragments (see, for example: Yilmaz et al., 2002 ). Together with contact O3—H3⋯O4, $[R_{2}^{2}]$ (8) ring motifs are formed in the crystal structure. Combined with another hydrogen bond involving the non-coordinating alcohol group, O1—H1⋯Cl1, a diperiodic framework is formed parallel to (101), based on $[R_{2}^{2}]$ (8) and $[R_{4}^{4}]$ (22) supramolecular motifs (Fig. 2). The last hydrogen bond, O4—H4⋯O1, expands the supramolecular network through the formation of centrosymmetric $[R_{4}^{4}]$ (16) and $[R_{4}^{4}]$ (20) rings (Fig. 3), affording a stable triperiodic crystal structure.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯Cl1ⁱ	0.83 (2)	2.24 (2)	3.068 (2)	174 (4)
O2—H2⋯O5ⁱⁱ	0.86 (2)	1.55 (2)	2.408 (3)	178 (4)
O3—H3⋯O4ⁱⁱⁱ	0.82 (2)	2.00 (2)	2.758 (3)	154 (4)
O4—H4⋯O1^iv	0.82 (2)	1.85 (2)	2.663 (3)	171 (4)
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iv) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Figure 2
The supramolecular framework based on intermolecular O—H⋯(O, Cl) hydrogen bonds (dashed blue lines) corresponding to entries 1–3 in Table 1

. The inset shows single crystals suitable for X-ray diffraction.

Figure 3
The supramolecular framework based on intermolecular O—H⋯O hydrogen bonds (dashed blue lines) corresponding to entries 2–4 in Table 1

Synthesis and crystallization

Single crystals of the title complex were unexpectedly obtained in an attempt to substitute the chlorido ligand in [Cu(H₅bis-tris)Cl]⁺ by a heterocyclic compound. Complex [Cu(H₅bis-tris)Cl]⁺Cl⁻ (1 mmol, 0.343 g) and fluconazole (1 mmol, 0.307 g) were dissolved in ethanol (70% v/v solution, 15 ml). The mixture was heated to 323 K under stirring for 20 min, and filtered to eliminate a blue precipitate. The resulting solution was evaporated over 3 days, affording a blue product. The crude product was recrystallized in methanol, giving sky-blue crystals used for the diffraction study (see Fig. 2, inset).

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	[Cu(C₈H₁₈NO₅)Cl]
M_r	307.22
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	109
a, b, c (Å)	7.2605 (9), 10.4221 (14), 14.668 (2)
β (°)	94.366 (12)
V (Å³)	1106.7 (3)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	2.22
Crystal size (mm)	0.17 × 0.06 × 0.04

Data collection
Diffractometer	Xcalibur, Atlas, Gemini
Absorption correction	Analytical (CrysAlis PRO; Rigaku OD, 2022 $[Rigaku OD (2022). CrysAlis PRO. Rigaku Oxford Diffraction Ltd, Yarnton, England.]$ )
T_min, T_max	0.848, 0.917
No. of measured, independent and observed [I > 2σ(I)] reflections	5523, 2582, 2002
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.694

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.130, 1.05
No. of reflections	2582
No. of parameters	157
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.18, −1.17
Computer programs: CrysAlis PRO (Rigaku OD, 2022 $[Rigaku OD (2022). CrysAlis PRO. Rigaku Oxford Diffraction Ltd, Yarnton, England.]$ ), SHELXT2018/2 (Sheldrick, 2015a ), SHELXL2018/3 (Sheldrick, 2015b ), XP in SHELXTL-Plus (Sheldrick, 2008 ), Mercury (Macrae et al., 2020 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 2355145

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314624004395/wm4213sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314624004395/wm4213Isup2.hkl

checkCIF report

Computing details top

Chlorido(2-{(2-hydroxyethyl)[tris(hydroxymethyl)methyl]amino}ethanolato-κ⁵N,O,O',O'',O''')copper(II) top

Crystal data top

[Cu(C₈H₁₈NO₅)Cl]	D_x = 1.844 Mg m⁻³
M_r = 307.22	Melting point: 435 K
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.2605 (9) Å	Cell parameters from 1395 reflections
b = 10.4221 (14) Å	θ = 3.4–29.6°
c = 14.668 (2) Å	µ = 2.22 mm⁻¹
β = 94.366 (12)°	T = 109 K
V = 1106.7 (3) Å³	Prism, blue
Z = 4	0.17 × 0.06 × 0.04 mm
F(000) = 636

Data collection top

Xcalibur, Atlas, Gemini diffractometer	2582 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2002 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.046
Detector resolution: 10.4685 pixels mm^-1	θ_max = 29.6°, θ_min = 3.4°
ω scans	h = −9→10
Absorption correction: analytical (CrysAlisPro; Rigaku OD, 2022)	k = −14→13
T_min = 0.848, T_max = 0.917	l = −18→18
5523 measured reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.048	Hydrogen site location: mixed
wR(F²) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0646P)²] where P = (F_o² + 2F_c²)/3
2582 reflections	(Δ/σ)_max = 0.001
157 parameters	Δρ_max = 1.18 e Å⁻³
4 restraints	Δρ_min = −1.17 e Å⁻³
0 constraints

Special details top

Refinement. Methylene H atoms were refined using a riding model (C—H: 0.99 Å); hydroxy H atoms (H1, H2, H3, H4) were located from electron-difference maps and were refined freely, with the O—H bond lengths restrained to 0.85 (2) Å.

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

	x	y	z	U_iso*/U_eq
Cu1	0.22842 (5)	0.75373 (4)	0.75931 (3)	0.00775 (16)
Cl1	0.31899 (12)	0.76196 (8)	0.61387 (6)	0.0145 (2)
O1	0.2269 (3)	0.8024 (2)	1.09572 (16)	0.0130 (5)
H1	0.116 (3)	0.790 (4)	1.103 (3)	0.019*
O2	0.3908 (3)	0.6168 (2)	0.80600 (16)	0.0096 (5)
H2	0.407 (5)	0.539 (2)	0.790 (3)	0.014*
O3	0.4592 (3)	0.8730 (2)	0.84389 (17)	0.0143 (5)
H3	0.462 (5)	0.9507 (19)	0.836 (3)	0.022*
O4	−0.0338 (3)	0.6104 (2)	0.72784 (16)	0.0104 (5)
H4	−0.113 (4)	0.641 (4)	0.692 (2)	0.016*
O5	0.0620 (3)	0.8995 (2)	0.74310 (16)	0.0111 (5)
N1	0.1319 (4)	0.7390 (2)	0.8869 (2)	0.0075 (6)
C1	0.3128 (5)	0.7294 (3)	0.9443 (2)	0.0080 (7)
C2	0.2964 (5)	0.6976 (3)	1.0446 (2)	0.0121 (7)
H2A	0.213089	0.622927	1.048817	0.015*
H2B	0.419525	0.672641	1.072706	0.015*
C3	0.4235 (4)	0.6194 (3)	0.9021 (2)	0.0109 (7)
H3A	0.557130	0.631837	0.918562	0.013*
H3B	0.386836	0.536144	0.927768	0.013*
C4	0.4244 (4)	0.8542 (3)	0.9372 (2)	0.0104 (7)
H4A	0.353726	0.927666	0.959330	0.012*
H4B	0.542532	0.847779	0.975361	0.012*
C5	0.0232 (4)	0.6181 (3)	0.8917 (2)	0.0096 (7)
H5A	−0.039617	0.617991	0.949336	0.012*
H5B	0.109414	0.544400	0.893907	0.012*
C6	−0.1206 (4)	0.5993 (3)	0.8123 (2)	0.0118 (7)
H6A	−0.178021	0.513531	0.816363	0.014*
H6B	−0.218735	0.664857	0.814672	0.014*
C7	0.0172 (4)	0.8544 (3)	0.9019 (2)	0.0094 (7)
H7A	0.095096	0.922177	0.932473	0.011*
H7B	−0.081487	0.832157	0.942142	0.011*
C8	−0.0692 (4)	0.9044 (3)	0.8101 (2)	0.0114 (7)
H8A	−0.177933	0.851406	0.789966	0.014*
H8B	−0.111298	0.993927	0.817219	0.014*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0099 (3)	0.0069 (2)	0.0065 (2)	0.00093 (15)	0.00096 (17)	0.00036 (15)
Cl1	0.0135 (4)	0.0219 (5)	0.0084 (4)	0.0024 (3)	0.0025 (3)	0.0011 (3)
O1	0.0108 (11)	0.0173 (13)	0.0108 (13)	−0.0005 (11)	0.0007 (9)	−0.0040 (11)
O2	0.0163 (11)	0.0046 (11)	0.0080 (12)	0.0047 (10)	0.0018 (9)	−0.0025 (10)
O3	0.0218 (12)	0.0108 (11)	0.0110 (13)	−0.0061 (11)	0.0049 (10)	0.0006 (11)
O4	0.0128 (11)	0.0111 (12)	0.0073 (12)	−0.0009 (10)	−0.0007 (9)	0.0000 (10)
O5	0.0154 (11)	0.0085 (11)	0.0100 (12)	0.0031 (10)	0.0037 (9)	0.0011 (10)
N1	0.0095 (13)	0.0039 (13)	0.0088 (14)	0.0006 (10)	−0.0011 (11)	−0.0011 (11)
C1	0.0085 (15)	0.0082 (15)	0.0070 (16)	−0.0009 (13)	−0.0022 (12)	−0.0015 (13)
C2	0.0128 (16)	0.0119 (16)	0.0114 (18)	0.0007 (14)	−0.0012 (13)	−0.0009 (15)
C3	0.0114 (15)	0.0090 (16)	0.0121 (18)	0.0007 (14)	−0.0011 (12)	0.0020 (14)
C4	0.0120 (15)	0.0078 (16)	0.0112 (18)	−0.0019 (14)	0.0001 (12)	−0.0028 (13)
C5	0.0119 (15)	0.0090 (15)	0.0075 (16)	−0.0004 (14)	−0.0013 (12)	0.0018 (14)
C6	0.0137 (15)	0.0113 (16)	0.0101 (17)	−0.0055 (14)	−0.0015 (12)	0.0021 (14)
C7	0.0102 (15)	0.0105 (16)	0.0076 (17)	0.0038 (13)	0.0010 (12)	0.0011 (13)
C8	0.0124 (15)	0.0115 (16)	0.0102 (17)	0.0004 (14)	0.0012 (12)	0.0014 (14)

Geometric parameters (Å, º) top

Cu1—O2	1.943 (2)	C1—C4	1.540 (4)
Cu1—O5	1.944 (2)	C1—C3	1.556 (5)
Cu1—N1	2.054 (3)	C2—H2A	0.9900
Cu1—Cl1	2.2812 (10)	C2—H2B	0.9900
Cu1—O3	2.361 (3)	C3—H3A	0.9900
Cu1—O4	2.436 (2)	C3—H3B	0.9900
O1—C2	1.438 (4)	C4—H4A	0.9900
O1—H1	0.833 (19)	C4—H4B	0.9900
O2—C3	1.412 (4)	C5—C6	1.516 (4)
O2—H2	0.856 (19)	C5—H5A	0.9900
O3—C4	1.425 (4)	C5—H5B	0.9900
O3—H3	0.818 (19)	C6—H6A	0.9900
O4—C6	1.437 (4)	C6—H6B	0.9900
O4—H4	0.819 (18)	C7—C8	1.534 (5)
O5—C8	1.420 (4)	C7—H7A	0.9900
N1—C7	1.489 (4)	C7—H7B	0.9900
N1—C5	1.491 (4)	C8—H8A	0.9900
N1—C1	1.509 (4)	C8—H8B	0.9900
C1—C2	1.522 (5)

O2—Cu1—O5	166.42 (10)	C1—C2—H2A	108.9
O2—Cu1—N1	82.17 (10)	O1—C2—H2B	108.9
O5—Cu1—N1	85.29 (10)	C1—C2—H2B	108.9
O2—Cu1—Cl1	98.45 (7)	H2A—C2—H2B	107.7
O5—Cu1—Cl1	94.41 (7)	O2—C3—C1	111.0 (3)
N1—Cu1—Cl1	176.13 (8)	O2—C3—H3A	109.4
O2—Cu1—O3	79.29 (9)	C1—C3—H3A	109.4
O5—Cu1—O3	93.57 (9)	O2—C3—H3B	109.4
N1—Cu1—O3	80.70 (10)	C1—C3—H3B	109.4
Cl1—Cu1—O3	103.18 (7)	H3A—C3—H3B	108.0
O2—Cu1—O4	93.48 (9)	O3—C4—C1	108.3 (3)
O5—Cu1—O4	89.25 (9)	O3—C4—H4A	110.0
N1—Cu1—O4	79.10 (10)	C1—C4—H4A	110.0
Cl1—Cu1—O4	97.04 (6)	O3—C4—H4B	110.0
O3—Cu1—O4	159.29 (9)	C1—C4—H4B	110.0
C2—O1—H1	110 (3)	H4A—C4—H4B	108.4
C3—O2—Cu1	112.91 (19)	N1—C5—C6	114.1 (3)
C3—O2—H2	106 (3)	N1—C5—H5A	108.7
Cu1—O2—H2	134 (3)	C6—C5—H5A	108.7
C4—O3—Cu1	105.16 (18)	N1—C5—H5B	108.7
C4—O3—H3	106 (3)	C6—C5—H5B	108.7
Cu1—O3—H3	118 (3)	H5A—C5—H5B	107.6
C6—O4—Cu1	105.88 (18)	O4—C6—C5	109.3 (3)
C6—O4—H4	105 (3)	O4—C6—H6A	109.8
Cu1—O4—H4	113 (3)	C5—C6—H6A	109.8
C8—O5—Cu1	112.74 (19)	O4—C6—H6B	109.8
C7—N1—C5	111.8 (3)	C5—C6—H6B	109.8
C7—N1—C1	116.3 (3)	H6A—C6—H6B	108.3
C5—N1—C1	111.1 (2)	N1—C7—C8	109.9 (3)
C7—N1—Cu1	107.9 (2)	N1—C7—H7A	109.7
C5—N1—Cu1	109.0 (2)	C8—C7—H7A	109.7
C1—N1—Cu1	99.8 (2)	N1—C7—H7B	109.7
N1—C1—C2	115.2 (3)	C8—C7—H7B	109.7
N1—C1—C4	110.3 (3)	H7A—C7—H7B	108.2
C2—C1—C4	109.3 (3)	O5—C8—C7	110.1 (3)
N1—C1—C3	106.3 (3)	O5—C8—H8A	109.6
C2—C1—C3	107.7 (3)	C7—C8—H8A	109.6
C4—C1—C3	107.8 (3)	O5—C8—H8B	109.6
O1—C2—C1	113.2 (3)	C7—C8—H8B	109.6
O1—C2—H2A	108.9	H8A—C8—H8B	108.1

C7—N1—C1—C2	72.7 (4)	C4—C1—C3—O2	−82.8 (3)
C5—N1—C1—C2	−56.7 (4)	Cu1—O3—C4—C1	22.4 (3)
Cu1—N1—C1—C2	−171.5 (2)	N1—C1—C4—O3	−60.1 (3)
C7—N1—C1—C4	−51.5 (4)	C2—C1—C4—O3	172.3 (3)
C5—N1—C1—C4	179.1 (3)	C3—C1—C4—O3	55.5 (3)
Cu1—N1—C1—C4	64.2 (3)	C7—N1—C5—C6	69.7 (4)
C7—N1—C1—C3	−168.1 (3)	C1—N1—C5—C6	−158.5 (3)
C5—N1—C1—C3	62.5 (3)	Cu1—N1—C5—C6	−49.5 (3)
Cu1—N1—C1—C3	−52.3 (3)	Cu1—O4—C6—C5	−28.5 (3)
N1—C1—C2—O1	−72.4 (3)	N1—C5—C6—O4	53.5 (4)
C4—C1—C2—O1	52.4 (4)	C5—N1—C7—C8	−91.3 (3)
C3—C1—C2—O1	169.2 (2)	C1—N1—C7—C8	139.7 (3)
Cu1—O2—C3—C1	2.2 (3)	Cu1—N1—C7—C8	28.6 (3)
N1—C1—C3—O2	35.5 (3)	Cu1—O5—C8—C7	34.4 (3)
C2—C1—C3—O2	159.4 (3)	N1—C7—C8—O5	−41.6 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···Cl1ⁱ	0.83 (2)	2.24 (2)	3.068 (2)	174 (4)
O2—H2···O5ⁱⁱ	0.86 (2)	1.55 (2)	2.408 (3)	178 (4)
O3—H3···O4ⁱⁱⁱ	0.82 (2)	2.00 (2)	2.758 (3)	154 (4)
O4—H4···O1^iv	0.82 (2)	1.85 (2)	2.663 (3)	171 (4)
C4—H4B···Cl1^v	0.99	2.97	3.906 (3)	157
C5—H5A···Cl1ⁱ	0.99	2.97	3.887 (4)	155
C7—H7B···Cl1ⁱ	0.99	2.85	3.727 (3)	148
C8—H8B···O1^vi	0.99	2.65	3.577 (4)	157

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

Acknowledgements

The authors thank Dr Marcos Flores Alamo (Facultad de Química, UNAM, Mexico) for the data collection.

Funding information

Funding for this research was provided by: Vicerrectoría de Investigación y Estudios de Posgrado, Benemérita Universidad Autónoma de Puebla (grant No. 00030 to Grupos de investigación interdisciplinaria 2023); Consejo Nacional de Ciencia y Tecnología (scholarship No. 1064640 to MF-V).

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