Benzene-1,2,4,5-tetrol

Weare, B.L.; Hoggett, S.; Cull, W.J.; Argent, S.P.; Khlobystov, A.N.; Brown, P.D.

doi:10.1107/S2414314624006126

organic compounds

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ISSN: 2414-3146

Volume 9| Part 6| June 2024| x240612

https://doi.org/10.1107/S2414314624006126

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Benzene-1,2,4,5-tetrol

Benjamin L. Weare,^a ^* Sean Hoggett,^b William J. Cull,^b Stephen P. Argent,^b Andrei N. Khlobystov ^b and Paul D. Brown ^c

^aNanoscale and Microscale Research Centre, University of Nottingham, Nottingham, NG7 2RD, United Kingdom, ^bSchool of Chemistry, University of Nottingham, Nottingham, NG7 2RD, United Kingdom, and ^cDepartment of Mechanical, Materials, & Manufacturing Engineering, Faculty of Engineering, University of Nottingham, Nottingham, NG7 2RD, United Kingdom
^*Correspondence e-mail: benjamin.weare1@nottingham.ac.uk

Edited by I. Brito, University of Antofagasta, Chile (Received 4 June 2024; accepted 24 June 2024; online 28 June 2024)

The crystal structure of the title compound was determined at 120 K. It crystallizes in the triclinic space group P $[\overline{1}]$ with four independent molecules in the asymmetric unit. In the crystal, each symmetry-unique molecule forms π–π stacks on itself, giving four unique π–π stacking interactions. Intermolecular hydrogen bonding is observed between each pair of independent molecules, where each hydroxy group can act as a hydrogen-bond donor and acceptor.

Keywords: benzene-1,2,4,5-tetrol; crystal structure; hydrogen bonds; covalent organic framework; hydroxyl.

CCDC reference: 2357698

Structure description

Benzene-1,2,4,5-tetrol, a derivative of 2,5-dihydroxy-1,4-benzoquinone, has seen extensive use as a precursor to functionalized benzenes as well as more complex molecules and ligands. It has been used to access a number of more complex organic structures, such as phosphorous-containing ligands for transition-metal complexes (Pandey et al., 2019 ) or to bridge metal centres in complexes (Wellala et al., 2018 ). In recent years benzene-1,2,4,5-tetrol has found a niche as a monomer for the synthesis of polymers, coordination polymers, covalent organic frameworks, and a variety of other supramolecular structures. It has seen extensive use in the synthesis of framework polymers where it acts as a linear monomer linking other structural units. Recent examples include combining benzene-1,2,4,5-tetrol with a boronic acid-containing porphyrin, a two-dimensional square-pored boronate ester covalent organic framework (COF), creating a thin film that could be integrated into a field-effect transistor (Park et al., 2020 ), as well as the creation of hafnium- and zirconium-containing coordination polymers with water sorption properties, using benzene-1,2,4,5-tetrol as a linker (Poschmann et al., 2021 ). Benzene-1,2,4,5-tetrol has also been used in the synthesis of a variety of other COFs (Rondelli et al., 2023 ; Dalapati et al., 2015 ; Ma et al., 2013 ; Lanni et al., 2011 ), coordination polymers (Abrahams et al., 2016 ), supramolecular structures (Jia et al., 2015 ; Niu et al., 2006 ; Nakabayashi & Ohkoshi, 2009 ; Yuan et al., 2012 ), and polymers (Christinat et al., 2007 ; Rambo & Lavigne, 2007 ; Nishiyabu et al., 2012 ).

Despite of the ongoing interest in benzene-1,2,4,5-tetrol as a reagent, which stretches back at least a century (Mukerji, 1922 ), the crystal structure has only been solved as a water solvate and a co-crystal with 2,5-dihydroxy-1,4-benzoquinone (Jene et al., 2001 ). A search of the Cambridge Structure Database (WebCSD, December 2023) for the molecular structure of 1,2,4,5-benzenetetrol gave three results: 1,2,4,5-tetrahydroxybenzene monohydrate (QOGMAA; Jene et al., 2001); and 1,2,4,5-tetrahydroxybenzene 2,5-dihydroxy-1,4-benzoquinone (QOGMII, QOGMII01; Jene et al., 2001). Here we present the crystal structure of benzene-1,2,4,5-tetrol for the first time, which we anticipate will be of use for the synthetic chemical community in future endeavours.

At 120 K the structure was found to crystallize in the triclinic space group P $[\overline{1}]$ with the asymmetric unit containing four independent molecules of benzene-1,2,4,5-tetrol labelled A, B, C and D (Figs. 1, 2a). Each symmetry unique molecule forms π–π stacks on itself, i.e. molecule A forms a stack consisting entirely of molecule A (Fig. 2b). This gives four unique π–π stacking interactions with centroid-to-distances of 3.7474 (11) Å, while the perpendicular centroid-to-plane distances are 3.4457 (7) Å (molecule A), 3.5166 (8) Å (molecule B), 3.5653 (8) Å (molecule C), and 3.5653 (8) Å (molecule D). Intermolecular hydrogen bonding is observed between each pair of molecules, where each hydroxy group can act as a hydrogen-bond donor and acceptor (Table 1). This creates an extended hydrogen-bond network, which can be described as a series of rings consisting of three molecules – the edges of two molecules make up the perimeter of the ring, and a single hydroxy group of a third molecule links the first two molecules into a continuous ring. There are two unique rings comprised of molecules A, B, and C, and of molecules C, B, and D, both of which exhibit an R₂²(14) graph-set motif, and the remaining hydrogen-bonded rings are symmetry-related. All of the hydrogen bonds in the structure can thus be accounted for.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4A—H4A⋯O4Cⁱ	0.85 (2)	1.89 (2)	2.715 (2)	163 (2)
O4B—H4B⋯O4Dⁱⁱ	0.86 (2)	1.88 (2)	2.708 (2)	163 (3)
O4B—H4B⋯O5B	0.86 (2)	2.45 (2)	2.764 (2)	102 (2)
O4C—H4C⋯O4B	0.86 (2)	1.85 (2)	2.702 (2)	167 (2)
O4D—H4D⋯O5B	0.86 (2)	1.85 (2)	2.6425 (19)	154 (2)
O4D—H4D⋯O5D	0.86 (2)	2.34 (2)	2.789 (2)	113 (2)
O5A—H5A⋯O4A	0.83 (2)	2.40 (2)	2.711 (2)	103 (2)
O5A—H5A⋯O5Dⁱⁱ	0.83 (2)	1.95 (2)	2.7562 (18)	162 (2)
O5B—H5B⋯O5A	0.84 (2)	1.80 (2)	2.633 (2)	169 (2)
O5C—H5C⋯O4Aⁱⁱⁱ	0.83 (2)	2.04 (2)	2.8376 (16)	161 (2)
O5C—H5C⋯O4C	0.83 (2)	2.38 (2)	2.734 (2)	107 (2)
O5D—H5D⋯O5C^iv	0.85 (2)	2.03 (2)	2.8796 (19)	175 (2)
Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .

Figure 1
The asymmetric unit of the title compound showing the atom labelling with 50% probability displacement ellipsoids. Unlabelled atoms are related to labelled atoms by the symmetry operations −x, −y + 2, −z for molecule A, −x + 1, −y + 1, −z for molecule B, −x + 1, −y, −z + 1 for molecule C and −x + 2, −y + 1, −z + 1 for molecule D.

Figure 2
(a) View of unit cell along the crystallographic a-axis. Dashed lines represent hydrogen bonding between molecules. R₂²(14) rings are indicated with purple and green polygons; hydrogen bonds not lying on the indicated rings form the same class of ring with molecules not rendered in this diagram. (b) View approximately along the (001) axis, showing how molecules form π–π stacks. Some molecules have been removed for clarity.

Synthesis and crystallization

Following a literature procedure (Weider et al., 1985 ), 2,5-dihydroxy-1,4-benzoquinone (2.428 g, 17.3 mmol) was mixed with conc. hydrochloric acid (54 ml) under an inert atmosphere and stirred for 30 min to form a gold-coloured suspension. Addition of tin metal powder (2.1885 g, 18.4 mmol) caused vigorous effervescence and a grey suspension. The mixture was stirred for 10 min until cessation of bubbling then heated to 100° C for 1 h, during which time the mixture became dark and bubbled vigorously. The mixture was allowed to cool briefly, then hot filtered under reduced pressure to give a yellow filtrate. The filtrate was cooled on ice for 30 min to give white crystals of benzene-1,2,4,5-tetrol (0.786 g, 5.54 mmol, 32%). The crude product was dissolved in a minimum of hot tetrahydrofuran, filtered, then cooled on ice. The resulting white crystals were collected via filtration then washed with ice-cold THF and dried in a vacuum to give benzene-1,2,4,5-tetrol (0.735 g, 5.17 mmol, 30%). IR (ATR) ν_max /cm⁻¹: 3146.01 br (OH), 1551.54 s (Ar C—C), 1155.90 w (C—O) MS (ESI) m/z: 165.02 (M+Na). ¹H NMR (400 MHz, DMSO-d₆, p.p.m., δ): 9.66 (s, 4H, OH), 5.94 (s, 2H, Ar H); ¹³C NMR (400 MHz, DMSO-d₆, p.p.m., δ): 138.46, 104.81. CNH analysis found: C, 50.6; H, 4.1; N, 0. Calculated for C₆H₆O₄: C, 50.7; H, 4.3; N, 0%.

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	C₆H₆O₄
M_r	142.11
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	120
a, b, c (Å)	3.7474 (2), 11.6254 (6), 13.7771 (8)
α, β, γ (°)	68.407 (5), 85.779 (4), 89.843 (4)
V (Å³)	556.37 (6)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	1.27
Crystal size (mm)	0.07 × 0.05 × 0.02

Data collection
Diffractometer	XtalLAB PRO MM007, PILATUS3 R 200K
Absorption correction	Gaussian (CrysAlis PRO; Rigaku OD, 2023 $[Rigaku OD (2023). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ )
T_min, T_max	0.927, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	8096, 2185, 1842
R_int	0.063
(sin θ/λ)_max (Å⁻¹)	0.630

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.133, 1.09
No. of reflections	2185
No. of parameters	205
No. of restraints	8
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.34
Computer programs: CrysAlis PRO (Rigaku OD, 2023 $[Rigaku OD (2023). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ ), SHELXT2018/2 (Sheldrick, 2015a ), SHELXL2018/3 (Sheldrick, 2015b ) and OLEX2 (Dolomanov et al., 2009 ).

Structural data

CCDC reference: 2357698

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314624006126/bx4030sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314624006126/bx4030Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314624006126/bx4030Isup3.cml

checkCIF report

Computing details top

Benzene-1,2,4,5-tetrol top

Crystal data top

C₆H₆O₄	Z = 4
M_r = 142.11	F(000) = 296
Triclinic, P1	D_x = 1.697 Mg m⁻³
a = 3.7474 (2) Å	Cu Kα radiation, λ = 1.54184 Å
b = 11.6254 (6) Å	Cell parameters from 4683 reflections
c = 13.7771 (8) Å	θ = 3.4–75.6°
α = 68.407 (5)°	µ = 1.26 mm⁻¹
β = 85.779 (4)°	T = 120 K
γ = 89.843 (4)°	Block, colourless
V = 556.37 (6) Å³	0.07 × 0.05 × 0.02 mm

Data collection top

XtalLAB PRO MM007, PILATUS3 R 200K diffractometer	2185 independent reflections
Radiation source: rotating anode, MicroMax 007 HF	1842 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.063
Detector resolution: 5.8140 pixels mm^-1	θ_max = 76.2°, θ_min = 3.5°
ω scans	h = −4→4
Absorption correction: gaussian (CrysAlisPro; Rigaku OD, 2023)	k = −14→14
T_min = 0.927, T_max = 1.000	l = −17→17
8096 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)] = 0.045	Hydrogen site location: mixed
wR(F²) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ²(F_o²) + (0.0799P)² + 0.1541P] where P = (F_o² + 2F_c²)/3
2185 reflections	(Δ/σ)_max < 0.001
205 parameters	Δρ_max = 0.28 e Å⁻³
8 restraints	Δρ_min = −0.33 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. All hydrogen atoms were observed in the electron difference map. All hydroxy hydrogen atoms were refined with their O-H distances restrained to a target distance of 0.84 %A (DFIX). All other hydrogen atoms were geometrically placed and refined with a riding model.

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

	x	y	z	U_iso*/U_eq
C1A	−0.1468 (5)	1.09568 (17)	0.02598 (13)	0.0161 (4)
H1A	−0.249116	1.160936	0.043654	0.019*
C2A	−0.0561 (4)	0.98695 (17)	0.10428 (13)	0.0161 (4)
C3A	0.0876 (5)	0.89114 (17)	0.07847 (13)	0.0159 (4)
O4A	−0.1011 (3)	0.96812 (13)	0.20910 (9)	0.0204 (3)
H4A	−0.224 (6)	1.024 (2)	0.2205 (19)	0.031*
O5A	0.1865 (4)	0.78369 (12)	0.15524 (10)	0.0223 (3)
H5A	0.055 (6)	0.767 (2)	0.2104 (15)	0.033*
C1B	0.3702 (5)	0.38074 (17)	0.02176 (14)	0.0176 (4)
H1B	0.280395	0.299234	0.036481	0.021*
C2B	0.3851 (5)	0.42502 (17)	0.10209 (13)	0.0164 (4)
C3B	0.5136 (5)	0.54465 (17)	0.08035 (14)	0.0167 (4)
O4B	0.2720 (4)	0.34746 (13)	0.20260 (10)	0.0231 (3)
H4B	0.192 (7)	0.388 (2)	0.2403 (18)	0.035*
O5B	0.5337 (4)	0.58394 (13)	0.16233 (10)	0.0225 (3)
H5B	0.434 (7)	0.6521 (18)	0.1517 (19)	0.034*
C1C	0.5825 (5)	0.12616 (17)	0.45145 (13)	0.0168 (4)
H1C	0.639580	0.212043	0.418210	0.020*
C2C	0.4847 (5)	0.05791 (17)	0.39276 (13)	0.0167 (4)
C3C	0.4038 (5)	−0.06764 (17)	0.44063 (13)	0.0161 (4)
O4C	0.4713 (4)	0.10954 (12)	0.28510 (9)	0.0195 (3)
H4C	0.421 (6)	0.1868 (16)	0.2668 (18)	0.029*
O5C	0.3112 (3)	−0.13754 (12)	0.38383 (9)	0.0185 (3)
H5C	0.226 (6)	−0.093 (2)	0.3286 (14)	0.028*
C1D	1.0908 (4)	0.38787 (17)	0.49271 (13)	0.0159 (4)
H1D	1.153969	0.310947	0.487689	0.019*
C2D	0.9455 (4)	0.47869 (17)	0.40886 (13)	0.0149 (4)
C3D	0.8562 (4)	0.59139 (17)	0.41683 (13)	0.0151 (4)
O4D	0.8906 (4)	0.45066 (13)	0.32286 (9)	0.0202 (3)
H4D	0.773 (6)	0.509 (2)	0.2812 (17)	0.030*
O5D	0.7198 (3)	0.68082 (12)	0.33076 (9)	0.0180 (3)
H5D	0.611 (6)	0.7358 (19)	0.3477 (18)	0.027*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1A	0.0121 (8)	0.0164 (9)	0.0193 (9)	0.0051 (7)	−0.0046 (7)	−0.0052 (7)
C2A	0.0106 (8)	0.0201 (10)	0.0156 (8)	0.0037 (7)	−0.0036 (6)	−0.0039 (7)
C3A	0.0126 (8)	0.0159 (9)	0.0153 (8)	0.0037 (7)	−0.0049 (6)	−0.0003 (7)
O4A	0.0238 (7)	0.0217 (7)	0.0146 (6)	0.0096 (6)	−0.0051 (5)	−0.0046 (5)
O5A	0.0267 (7)	0.0185 (7)	0.0153 (6)	0.0120 (6)	−0.0023 (5)	0.0012 (5)
C1B	0.0142 (8)	0.0154 (9)	0.0215 (9)	0.0067 (7)	−0.0072 (7)	−0.0036 (7)
C2B	0.0128 (8)	0.0166 (9)	0.0162 (8)	0.0056 (7)	−0.0055 (7)	−0.0009 (7)
C3B	0.0136 (8)	0.0191 (9)	0.0183 (8)	0.0092 (7)	−0.0096 (7)	−0.0065 (7)
O4B	0.0302 (8)	0.0182 (7)	0.0171 (6)	0.0073 (6)	−0.0010 (5)	−0.0022 (5)
O5B	0.0309 (8)	0.0196 (7)	0.0195 (7)	0.0136 (6)	−0.0128 (6)	−0.0083 (6)
C1C	0.0143 (8)	0.0162 (9)	0.0172 (8)	0.0063 (7)	−0.0036 (7)	−0.0024 (7)
C2C	0.0130 (8)	0.0194 (10)	0.0133 (8)	0.0072 (7)	−0.0039 (6)	−0.0005 (7)
C3C	0.0119 (8)	0.0176 (9)	0.0171 (8)	0.0058 (7)	−0.0040 (6)	−0.0041 (7)
O4C	0.0264 (7)	0.0157 (7)	0.0138 (6)	0.0074 (6)	−0.0068 (5)	−0.0013 (5)
O5C	0.0210 (7)	0.0175 (7)	0.0154 (6)	0.0051 (6)	−0.0080 (5)	−0.0032 (5)
C1D	0.0123 (8)	0.0145 (9)	0.0183 (8)	0.0043 (7)	−0.0036 (7)	−0.0026 (7)
C2D	0.0103 (8)	0.0180 (9)	0.0148 (8)	0.0026 (7)	−0.0033 (6)	−0.0037 (7)
C3D	0.0120 (8)	0.0144 (9)	0.0150 (8)	0.0041 (7)	−0.0045 (6)	0.0000 (7)
O4D	0.0237 (7)	0.0210 (7)	0.0164 (6)	0.0107 (6)	−0.0094 (5)	−0.0062 (5)
O5D	0.0194 (6)	0.0171 (7)	0.0148 (6)	0.0092 (5)	−0.0075 (5)	−0.0015 (5)

Geometric parameters (Å, º) top

C1A—H1A	0.9500	C1C—H1C	0.9500
C1A—C2A	1.388 (2)	C1C—C2C	1.391 (3)
C1A—C3Aⁱ	1.391 (2)	C1C—C3Cⁱⁱⁱ	1.394 (2)
C2A—C3A	1.385 (3)	C2C—C3C	1.386 (3)
C2A—O4A	1.376 (2)	C2C—O4C	1.385 (2)
C3A—O5A	1.378 (2)	C3C—O5C	1.379 (2)
O4A—H4A	0.852 (17)	O4C—H4C	0.863 (17)
O5A—H5A	0.835 (17)	O5C—H5C	0.832 (16)
C1B—H1B	0.9500	C1D—H1D	0.9500
C1B—C2B	1.386 (2)	C1D—C2D	1.392 (2)
C1B—C3Bⁱⁱ	1.391 (3)	C1D—C3D^iv	1.382 (2)
C2B—C3B	1.390 (3)	C2D—C3D	1.392 (3)
C2B—O4B	1.381 (2)	C2D—O4D	1.368 (2)
C3B—O5B	1.372 (2)	C3D—O5D	1.3881 (19)
O4B—H4B	0.861 (16)	O4D—H4D	0.858 (16)
O5B—H5B	0.843 (17)	O5D—H5D	0.851 (16)

C2A—C1A—H1A	120.1	C2C—C1C—H1C	120.2
C2A—C1A—C3Aⁱ	119.82 (17)	C2C—C1C—C3Cⁱⁱⁱ	119.53 (18)
C3Aⁱ—C1A—H1A	120.1	C3Cⁱⁱⁱ—C1C—H1C	120.2
C3A—C2A—C1A	120.03 (16)	C3C—C2C—C1C	120.55 (16)
O4A—C2A—C1A	123.07 (16)	O4C—C2C—C1C	122.61 (17)
O4A—C2A—C3A	116.90 (15)	O4C—C2C—C3C	116.82 (16)
C2A—C3A—C1Aⁱ	120.14 (16)	C2C—C3C—C1Cⁱⁱⁱ	119.92 (17)
O5A—C3A—C1Aⁱ	119.11 (16)	O5C—C3C—C1Cⁱⁱⁱ	118.51 (17)
O5A—C3A—C2A	120.70 (15)	O5C—C3C—C2C	121.57 (15)
C2A—O4A—H4A	112.3 (16)	C2C—O4C—H4C	109.5 (15)
C3A—O5A—H5A	111.3 (17)	C3C—O5C—H5C	110.6 (17)
C2B—C1B—H1B	119.9	C2D—C1D—H1D	119.7
C2B—C1B—C3Bⁱⁱ	120.17 (18)	C3D^iv—C1D—H1D	119.7
C3Bⁱⁱ—C1B—H1B	119.9	C3D^iv—C1D—C2D	120.58 (17)
C1B—C2B—C3B	119.88 (17)	C1D—C2D—C3D	119.20 (16)
O4B—C2B—C1B	118.40 (17)	O4D—C2D—C1D	117.50 (16)
O4B—C2B—C3B	121.71 (16)	O4D—C2D—C3D	123.28 (15)
C2B—C3B—C1Bⁱⁱ	119.95 (17)	C1D^iv—C3D—C2D	120.22 (15)
O5B—C3B—C1Bⁱⁱ	121.84 (18)	C1D^iv—C3D—O5D	122.17 (16)
O5B—C3B—C2B	118.17 (16)	O5D—C3D—C2D	117.60 (15)
C2B—O4B—H4B	111.8 (18)	C2D—O4D—H4D	108.3 (17)
C3B—O5B—H5B	112.5 (16)	C3D—O5D—H5D	111.5 (16)

C1A—C2A—C3A—C1Aⁱ	1.1 (3)	C1C—C2C—C3C—C1Cⁱⁱⁱ	0.5 (3)
C1A—C2A—C3A—O5A	178.53 (16)	C1C—C2C—C3C—O5C	−179.04 (15)
C3Aⁱ—C1A—C2A—C3A	−1.0 (3)	C3Cⁱⁱⁱ—C1C—C2C—C3C	−0.5 (3)
C3Aⁱ—C1A—C2A—O4A	178.86 (16)	C3Cⁱⁱⁱ—C1C—C2C—O4C	−178.89 (15)
O4A—C2A—C3A—C1Aⁱ	−178.86 (16)	O4C—C2C—C3C—C1Cⁱⁱⁱ	178.98 (15)
O4A—C2A—C3A—O5A	−1.4 (3)	O4C—C2C—C3C—O5C	−0.6 (2)
C1B—C2B—C3B—C1Bⁱⁱ	−0.5 (3)	C1D—C2D—C3D—C1D^iv	−0.4 (3)
C1B—C2B—C3B—O5B	−178.19 (14)	C1D—C2D—C3D—O5D	178.51 (15)
C3Bⁱⁱ—C1B—C2B—C3B	0.5 (3)	C3D^iv—C1D—C2D—C3D	0.4 (3)
C3Bⁱⁱ—C1B—C2B—O4B	−179.07 (15)	C3D^iv—C1D—C2D—O4D	−178.16 (16)
O4B—C2B—C3B—C1Bⁱⁱ	179.06 (15)	O4D—C2D—C3D—C1D^iv	178.07 (17)
O4B—C2B—C3B—O5B	1.4 (2)	O4D—C2D—C3D—O5D	−3.0 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4A—H4A···O4C^v	0.85 (2)	1.89 (2)	2.715 (2)	163 (2)
O4B—H4B···O4D^vi	0.86 (2)	1.88 (2)	2.708 (2)	163 (3)
O4B—H4B···O5B	0.86 (2)	2.45 (2)	2.764 (2)	102 (2)
O4C—H4C···O4B	0.86 (2)	1.85 (2)	2.702 (2)	167 (2)
O4D—H4D···O5B	0.86 (2)	1.85 (2)	2.6425 (19)	154 (2)
O4D—H4D···O5D	0.86 (2)	2.34 (2)	2.789 (2)	113 (2)
O5A—H5A···O4A	0.83 (2)	2.40 (2)	2.711 (2)	103 (2)
O5A—H5A···O5D^vi	0.83 (2)	1.95 (2)	2.7562 (18)	162 (2)
O5B—H5B···O5A	0.84 (2)	1.80 (2)	2.633 (2)	169 (2)
O5C—H5C···O4A^vii	0.83 (2)	2.04 (2)	2.8376 (16)	161 (2)
O5C—H5C···O4C	0.83 (2)	2.38 (2)	2.734 (2)	107 (2)
O5D—H5D···O5C^viii	0.85 (2)	2.03 (2)	2.8796 (19)	175 (2)

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

Acknowledgements

The authors would like to thank T. Liu at the Analytical Services in the University of Nottingham School of Chemistry for performing thre CHN analysis. Author contributions are as follows: conceptualization, BLW; investigation, BLW, SH, WJC, SA; validation, BLW, SA; writing (original draft), BLW; writing (review and editing), BLW, SA, WJC, PDB, ANK; visualization, BLW; supervision, ANK, PDB; funding acquisition, ANK, PDB.

Funding information

Funding for this research was provided by: Engineering and Physical Sciences Research Council (grant No. EP/W006413/1); Leverhulme Trust (grant No. RPG-2022-300).

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Volume 9| Part 6| June 2024| x240612

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Benzene-1,2,4,5-tetrol

Structure description

Synthesis and crystallization

Refinement

Structural data

Acknowledgements

Funding information

References

organic compounds