Determination of the structure of benzene-1,2,4,5-tetrol
Keywords: benzene-1,2,4,5-tetrol; crystal structure; hydrogen bonds; covalent organic framework; hydroxyl
Abstract
The crystal structure of the title compound was determined at 120 K. It crystallizes in the triclinic space group P
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.
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 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. 2 ▸b). 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 
(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.
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. (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.
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⋯O5Civ | 0.85 (2) | 2.03 (2) | 2.8796 (19) | 175 (2) |
Symmetry codes: (i) 
; (ii) 
; (iii) 
; (iv) 
.
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) νmax /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
|
| 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 ▸) |
| Tmin, Tmax | 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 |
| Δρmax, Δρmin (e Å−3) | 0.28, −0.34 |
Supplementary Material
Crystal structure: contains datablock(s) I. DOI: 10.1107/S2414314624006126/bx4030sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2414314624006126/bx4030Isup2.hkl
Supporting information file. DOI: 10.1107/S2414314624006126/bx4030Isup3.cml
CCDC reference: 2357698
Additional supporting information: crystallographic information; 3D view; checkCIF report
Acknowledgments
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.
full crystallographic data
Benzene-1,2,4,5-tetrol. Crystal data
| C6H6O4 | Z = 4 |
| Mr = 142.11 | F(000) = 296 |
| Triclinic, P1 | Dx = 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 |
Benzene-1,2,4,5-tetrol. Data collection
| 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 | Rint = 0.063 |
| Detector resolution: 5.8140 pixels mm-1 | θmax = 76.2°, θmin = 3.5° |
| ω scans | h = −4→4 |
| Absorption correction: gaussian (CrysAlisPro; Rigaku OD, 2023) | k = −14→14 |
| Tmin = 0.927, Tmax = 1.000 | l = −17→17 |
| 8096 measured reflections |
Benzene-1,2,4,5-tetrol. Refinement
| 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(Fo2) + (0.0799P)2 + 0.1541P] where P = (Fo2 + 2Fc2)/3 |
| 2185 reflections | (Δ/σ)max < 0.001 |
| 205 parameters | Δρmax = 0.28 e Å−3 |
| 8 restraints | Δρmin = −0.33 e Å−3 |
Benzene-1,2,4,5-tetrol. Special details
| 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. |
Benzene-1,2,4,5-tetrol. Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| 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* |
Benzene-1,2,4,5-tetrol. Atomic displacement parameters (Å2)
| 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) |
Benzene-1,2,4,5-tetrol. Geometric parameters (Å, º)
| 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—C3Div | 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) | C3Div—C1D—H1D | 119.7 |
| C3Bii—C1B—H1B | 119.9 | C3Div—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) | C1Div—C3D—C2D | 120.22 (15) |
| O5B—C3B—C1Bii | 121.84 (18) | C1Div—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—C1Div | −0.4 (3) |
| C1B—C2B—C3B—O5B | −178.19 (14) | C1D—C2D—C3D—O5D | 178.51 (15) |
| C3Bii—C1B—C2B—C3B | 0.5 (3) | C3Div—C1D—C2D—C3D | 0.4 (3) |
| C3Bii—C1B—C2B—O4B | −179.07 (15) | C3Div—C1D—C2D—O4D | −178.16 (16) |
| O4B—C2B—C3B—C1Bii | 179.06 (15) | O4D—C2D—C3D—C1Div | 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.
Benzene-1,2,4,5-tetrol. Hydrogen-bond geometry (Å, º)
| D—H···A | D—H | H···A | D···A | D—H···A |
| O4A—H4A···O4Cv | 0.85 (2) | 1.89 (2) | 2.715 (2) | 163 (2) |
| O4B—H4B···O4Dvi | 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···O5Dvi | 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···O4Avii | 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···O5Cviii | 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.
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) I. DOI: 10.1107/S2414314624006126/bx4030sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2414314624006126/bx4030Isup2.hkl
Supporting information file. DOI: 10.1107/S2414314624006126/bx4030Isup3.cml
CCDC reference: 2357698
Additional supporting information: crystallographic information; 3D view; checkCIF report