Structural insight into piezo-solvatochromism of Reichardt's dye

To date, accurate modelling of the solvation process is challenging, often over-simplifying the solvent–solute interactions. The interplay between the molecular arrangement associated with the solvation process and crystal nucleation has been investigated by analysis of the piezo-solvatochromic behaviour of Reichardt's dye, ET(1), in methanol, ethanol and acetone under high pressure. High-pressure single-crystal X-ray diffraction and UV–Vis spectroscopy reveal the impact of solute–solvent interactions on the optical properties of ET(1). The study underscores the intricate relationship between solvent properties, molecular conformation and crystal packing. The connection between liquid and solid phases emphasizes the capabilities of high-pressure methods for expanding the field of crystal engineering. The high-pressure environment allowed the determination of the crystal structures reported here that are built from organic molecules fourfold solvated with ethanol or methanol: ET(1)·4CH₃OH and ET(1)·4C₂H₅OH·H₂O. The observed piezo-solvatochromic effects highlight the potential of ET(1) in nonlinear optoelectronics and expand the application of solvatochromic chemical indicators to pressure sensors.

1. Introduction

Molecular interactions, especially those between solute and solvent molecules, have been the subject of intense scientific investigations for decades (Henkel et al., 2018; Buncel & Stairs, 2015; Walker et al., 1992; Mabesoone et al., 2020; Laurence et al., 1994). A particularly intriguing manifestation of these interactions is solvatochromism (Nigam & Rutan, 2001; Marini et al., 2010; Bamfield & Hutchings, 2018), i.e. the dependence of absorption of a dye solution on the liquid environment (Reichardt & Welton, 2010; Machado et al., 2014; Reichardt, 1994). This phenomenon, manifested as a colour change, not only provides a visual representation of dye–solvent interactions, but also offers a deep insight into the underlying forces (Plenert et al., 2021; Spange et al., 2022) such as hydrogen bonds, dipole–dipole and van der Waals interactions that play a pivotal role for the physicochemical properties of dye solutions (Reichardt, 2004). However, no structural information about the aggregation modes of the dye and solvent molecules, which could be directly connected with the solvatochromic effects, is available. For the first time, we have employed the techniques of high-pressure crystallization, in situ X-ray diffraction and UV–Vis spectroscopy to fill this gap in understanding solvatochromism. It is known that high pressure increases the preference for the formation of solvates, which are often unstable under atmospheric pressure (Bhardwaj et al., 2019; Boldyreva, 2007; Fabbiani et al., 2004, 2010; Fabbiani & Pulham, 2006; Katrusiak, 2019; Marciniak et al., 2016; Olejniczak et al., 2016; Oswald et al., 2009; Safari et al., 2020; Tomkowiak et al., 2013; Tumanov et al., 2010). Our results unveil the interesting interplay between solvent polarity and molecular interactions relevant to various fields of chemistry. The practical aspects of this knowledge involve designing new compounds, chemical synthesis as well as materials science and biochemistry (Reichardt & Welton, 2010; Buncel & Stairs, 2015), for example, for developing sensors and drugs (Reichardt, 2004; Lee et al., 2013; Klymchenko, 2017). The solvatochromic effects observed in organic compounds, attributed to their high molecular hyperpolarizability, have spurred interest in their potential applications in nonlinear optoelectronics (Mairesse et al., 2023; Nie, 1993; Zyss & Ledoux, 1994; Champagne & Bishop, 2003).

A group of pyridinium N-betaine organic dyes, often referred to as Reichardt's dyes, is particularly sensitive to changes in the solvent environment and thus used to probe solvent–solute interactions (Reichardt, 1994; Machado et al., 2014; Dimroth et al., 1963). The molecules of Reichardt's dyes comprise an extended conjugated and polarizable system, with a large permanent dipole moment (Budzák et al., 2017; Walker et al., 1992). Additionally, the oxygen atom on the phenolate moiety is highly basic and prone to form of hydrogen bonds with solvent molecules (Spange & Weiß, 2023; Spange et al., 2022; Plenert et al., 2021). The simplest representative among the N-betaine dyes is 4-(2,4,6-tri­phenyl-1-pyridinio)phenolate, herein referred to as ET(1), shown in Fig. 1.

Figure 1 Zwitterion of ET(1) and its atomic labels.

In order to explore the structure–property relationships of solvatochromic effects, we applied high-pressure in situ crystallization to obtain and stabilize the ET(1) methanol and ethanol solvates, which have been investigated by high-pressure single-crystal X-ray diffraction. Through this comprehensive investigation, we aspire to deepen our understanding of the solvation and solvatomorphism phenomena, as well as establish high-pressure crystallization combined with high-pressure spectroscopy as the stage for future research and applications in this captivating domain.

2. Experimental

The most common synthetic approach to produce pyridinium N-phenolates is the procedure established by Dimroth et al. (1963), involving the reaction of a pyrylium salt with an amino­phenol, followed by the reaction of the protonated dye with sodium methoxide or sodium (or potassium) hydroxide. This synthesis yields red single crystals of ET(1) (Dimroth et al., 1963). The crystals analysed in the high-pressure experiments here were used without any further purification. A graphical scheme of the experimental procedure for the investigation piezo-solvatomorphism is illustrated in Fig. 2.

Figure 2 Schematic overview of experimental procedures.

2.1. High-pressure X-ray diffraction

The in situ crystallization of all solvates was conducted using a modified Merrill–Bassett diamond anvil cell (DAC) (Merrill & Bassett, 1974). For the experiments, a 0.3 mm-thick steel gasket with a 0.45 mm diameter hole was used. The single crystals were grown under isochoric conditions according to the following procedure: (i) red single crystals of ET(1) and a chosen solvent were loaded into the DAC chamber and compressed; (ii) the DAC was heated with a hot-air gun until all but one grain of ET(1) melted; (iii) through the controlled cooling of the DAC to room temperature, a single crystal was grown (Katrusiak, 2019). The temperature was monitored using an infrared thermometer and the pressure was calibrated with the ruby-fluorescence method before and after each X-ray diffraction analysis with a photon control spectrometer, affording an accuracy of 0.02 GPa (Mao et al., 1986; Piermarini et al., 1975).

Data collection and reduction were performed using the CrysAlisPro software (Rigaku, 2014). The crystal structures were solved and refined using SHELX (Sheldrick, 2008, 2015) within the Olex2 software (Dolomanov et al., 2009). Crystallographic data and experimental details are compiled in Table 1 and Table S1 of the supporting information, and have been deposited in CIF format in the Cambridge Crystallographic Database Centre (CCDC numbers provided). Structural illustrations were generated using Mercury (Macrae et al., 2008).

Table 1
Selected crystallographic data for the ET(1) solvates grown under ambient and high-pressure conditions

	ET(1)·5.78H2O	ET(1)·6H2O	ET(1)·4CH3OH		ET(1)·4CH3OH·H2O
Pressure (GPa)	0.0001†	0.22	0.57	1.17	0.24	0.76
Space group	C2221	C2221	P21/n	P21/n	R3c	R3c
Unit-cell parameters
a (Å)	15.005 (9)	15.311 (4)	10.4704 (11)	10.425 (3)	24.062 (9)	23.645 (8)
b (Å)	24.356 (4)	23.948 (6)	19.80 (3)	19.26 (7)	24.062 (9)	23.645 (8)
c (Å)	7.5097 (9)	7.27 (2)	13.3135 (15)	13.112 (4)	31.259 (8)	30.91 (2)
β (°)	–	–	95.819 (9)	95.70 (3)	–	–
Volume (Å^3)	2744.5 (17)	2664 (7)	2746 (4)	2620 (10)	15673 (9)	14966 (12)
Z/Z′	4/0.5	4/0.5	4/1	4/1	18/1	18/1
Dx (g cm^−3)	1.219	1.275	1.276	1.337	1.134	1.187

†Structural information adapted from WUKYEG determined by Stadnicka et al. (2002).

2.2. High-pressure optical absorption

UV–Vis measurements at high pressure were conducted with a Merrill–Bassett DAC equipped with type IIa diamonds, with 0.8 mm-diameter diamond culets. The gaskets were made of 0.1 mm-thick foil with a sparked-eroded hole 0.45 mm in diameter. Solutions of ET(1) (1.1 mM concentration) were prepared at room temperature and pressure and loaded into the DAC along with a small ruby chip, without any additional pressure-transmitting medium. High-pressure UV–Vis spectra were recorded using a Jasco V-770 spectrophotometer, adapted for the DAC. Absorbance measurements were carried out at a scan rate of 200 nm min⁻¹ in the 250–800 nm wavelength range.

3. Discussion and results

Solvation is a complex process that can be considered from many perspectives (Reichardt & Welton, 2010). This phenomenon can be considered on the level of the direct interactions formed between solute and solvent, often referred to as microsolvation (Rahbar & Stein, 2023). On the other hand, solvation can be viewed from the global perspective, where the solute molecules are stabilized by the general properties of the solvent, then called macrosolvation (Plenert et al., 2021). Both these approaches describing the solvent–solute environment are closely related, although they fail when strong, direct intermolecular interactions, such as electrostatic, van der Waals forces and hydrogen bonds affect the solvent–cluster conformation in the bulk solvent, which strongly influence the long-range solvent polarization effects (Plenert et al., 2021).

One of the most common empirical indicators used for determining the magnitude of the solvent–solute interactions is the ET(30) scale, introduced by Reichardt (1994) based on the solvatochromic response of 2,6-di­phenyl-4-(2,4,6-tri­phenyl­pyridinio)phenolate, often referred to as ET(30). The ET(30) scale is frequently used for measuring the molar electronic transition energies of pyridinium N-phenolate betaine dye in various solvents (Cerón-Carrasco et al., 2014). Although it was recently postulated that the ET(30) scale does not reflect the solvent `polarity' but rather the global polarity of alcoholic solvents represented by the number of OH groups per volume, i.e. hydroxyl-group density (Spange et al., 2022; Spange & Weiß, 2023), it is still used by many theoretical and experimental approaches for investigating complicated and entwined solvent–solute interactions.

3.1. Solvatochromism of ET(1) at high-pressure

All pyridinium N-phenolates demonstrate a typical spectrum with an intense short-wavelength main band around 300 nm, which is hardly influenced by solvents, and a weaker highly solvent-sensitive solvatochromic band or bands between 350 and 800 nm, often referred to as the intramolecular charge-transfer (λ_CT) absorption band (Dimroth et al., 1963; Reichardt, 2004, 1994; Machado et al., 2014). The position of the main absorption band (λ_max) is also frequently associated with the absorbance of the N-substituted 2,4,6-tri­phenyl-pyridinium cation, as the band position is preserved even after the addition of an acid to the solution mixture, while the solvatochromic bands disappear completely (Reichardt et al., 2001). The solvatochromic effect in this group of compounds was postulated to originate from differences between solvation spheres formed around the dye's highly dipolar electronic ground state and its less dipolar excited state (Reichardt, 1994). With increasing solvent polarity, the dipolar electronic ground state is more stabilized by the interaction with solvent than the less polar, excited state π–π*. The charge-transfer (CT) band of ET(1), like for other Reichardt's dyes, is extremely sensitive to the presence of water, especially in nonpolar solvents, to the point that contamination by the crystallization water can significantly alter the position of the CT band (Stadnicka et al., 2002).

The influence of the external pressure on the solvation process and on the interactions between organic solvents, often used in high-pressure techniques as pressure-transmitting media, remains unsolved and is frequently suggested as a reason behind unexpected phenomena (Zakharov et al., 2016; Zakharov & Boldyreva, 2019; Sobczak & Katrusiak, 2019). The spectroscopic investigation on the solutions of a model ET(30) betaine and 4-(pyridinium-1-yl)phenolate at high-pressure carried out previously by Drickamer's (Hammack et al., 1989) and Kelm's groups (Jouanne et al., 1978) confirm the expected shift of the CT absorption band to a shorter wavelength (higher frequency) with increasing pressure. This hypsochromic shift called piezo-solvatochromism (Machado et al., 2014) was postulated as a result of the pressure-supported stabilization of the dye's zwitterionic ground state. Furthermore, the observed changes in λ_max and λ_CT have been shown to correlate well with the increase of the dielectric function (ɛ_r − 1)/(ɛ_r + 2) of the solvent on compression (Hammack et al., 1989). This indicates that nonspecific solute/solvent interactions primarily govern the piezo-solvatochromic behaviour (Machado et al., 2014; Reichardt, 1992), whereas the solvents that can be involved in the formation of strong hydrogen bonds appear to be less sensitive to pressure changes (Reichardt, 1992).

In light of these findings, in order to better understand the solvation process we investigated the UV–Vis spectra at high-pressure of ET(1) solutions in three different polar solvents: methanol, ethanol and acetone (Fig. 3). The three distinct colours of those mixtures strongly correlate with the hydrogen-bonding capabilities of the solvents; ET(1) dissolved in methanol is yellow, in the ethanol solution it is red and in the acetone solution it is blue, as shown in Fig. 3 (Dimroth et al., 1963; Stadnicka et al., 2002). These ET(1) solutions were loaded into a DAC and their spectra were measured as a function of high pressure.

Figure 3 UV–Vis absorption of the ET(1) solution in (a) methanol, (b) ethanol and (c) acetone as a function of pressure. The inset plots show the changes in the maximum peak position with pressure. The photographs of vials with 1.1 mM solutions loaded in the DAC illustrate their colour at ambient pressure.

The UV–Vis spectra of a methanol solution collected at 0.03 GPa show λ_max at 311 nm and λ_CT at 458 nm [Fig. 3(a)]. The results correlate with previously reported values at room temperature and pressure, where λ_max was localized at 306 nm and λ_CT at 452.8 nm, the small inconsistency in the position of the bands can be related to the large width of peaks and the method chosen for locating the peak centre (Dimroth et al., 1963; Stadnicka et al., 2002). When pressure is increased to 1.77 GPa, λ_max blue-shifts linearly to 321 nm at a rate of Δλ_max = 5.75 nm GPa⁻¹. At the same time, the rate of hypsochromic shift of the CT band is Δλ_CT = 8.6 nm GPa⁻¹. Further compression of the solution leads to the crystallization of the solution occurring at about 0.07 GPa above the crystallization pressure of pure methanol at p_c = 3.5 GPa according to Allan et al. (1998). Interestingly, on approaching methanol crystallization, there are anomalous changes in the pressure dependence of the absorbance spectra. While the constant increase of λ_max reflects the growing strain and increased potential energy (E_p) of the ET(1) molecule, the hypsochromic trend for λ_CT is reversed above 3 GPa, where it becomes bathochromic. This unprecedented bathochromic shift to 456 nm above 4.33 GPa corresponds to the solvatochromic band position at around 0.3 GPa. This U-turn shift clearly shows that, while the zwitterionic form of the ET(1) is stabilized in the solvation sphere, the interactions formed with the solvent molecules are significantly altered above the hydro­static limit of the solvent.

Both characteristic bands λ_max = 308.5 and λ_CT = 480 nm measured at 0.06 GPa for the red-orange ethanol solution coincide with that reported at room temperature and pressure of λ_max = 307 nm and λ_CT = 478 nm (Dimroth et al., 1963; Stadnicka et al., 2002). Note that, although the wide and asymmetric shape of the CT band significantly hindered the accurate determination of the λ_CT maximum peak, the trend is clear [Fig. 3(b)]. On compression to 2.07 GPa, the monotonic bathochromic shift of λ_max to 321.8 nm takes place. The shift rate Δλ_max = 6.75 nm GPa⁻¹ indicates that the potential energy of molecule ET(1) compressed in ethanol is more strongly affected than in methanol. At the same time, the λ_CT shift is intriguing. Up to 0.65 GPa, the pressure shifts the CT band towards shorter wavelengths (Δλ_CT = 4.07 nm GPa⁻¹), but at higher pressure the changes are fourfold more pronounced, and at 1.34 GPa the Δλ_CT reaches 17.8 nm GPa⁻¹. Interestingly, above 2 GPa the observed bathochromic trend is reversed and at 2.07 GPa the CT band splits into λ_CT1 at 426.7 nm and λ_CT2 at 475.5 nm [Fig. 3(b)]. These unexpected changes in absorbance spectra precede the solidification of the solution at 2.32 GPa, about 0.5 GPa above the freezing pressure of pure ethanol (p_c = 1.8 GPa) (Anderson et al., 1998). Both split CT bands are hardly affected; further compression to 5.45 GPa red-shifts λ_CT1 to 424 nm and λ_CT2 to 474 nm. The non-hydro­static compression of ET(1) dissolved in ethanol shifts λ_max at 5.45 GPa to 325 nm.

The dark blue colour of the acetone solution is distinct from those of the methanol and ethanol solutions [Fig. 3(c)]. At 0.22 GPa the ET(1) absorbance band has a wide, rounded shape, and thus we decided to deconvolute this signal into two peaks: λ_max1 at 265.2 and λ_max2 at 298.9 nm. At this pressure, λ_CT can be located at 517 nm, which is significantly lower than the λ_CT = 561 nm reported previously at 0.1 MPa. This difference exceeds the expected pressure effect, which can be due to the shape of the CT band and some water contamination, proven to shift the λ_CT position by 2000 cm⁻¹. The compression does not shift the absorption bands as strongly as the protic solvents and λ_CT at 1.28 GPa is 516 nm. Although the bathochromic change of λ_CT is visible, the rate of pressure-induced shift is low, with Δλ_CT = 0.92 nm GPa⁻¹. The compression to 1.28 GPa also changes the λ_max1 and λ_max2 positions: λ_max1 becomes blue-shifted to 264.4 nm while λ_max2 is red-shifted to 301 nm. These opposite effects suggest that only λ_max1 can be directly associated with the E_p increase of the ET(1) molecule, whereas for λ_max2 some contributions of the solvation sphere are apparent. Above 1.39 GPa, the strong changes in shape and peak position are visible, which precede the observed solidification of the mixture at 1.78 GPa, 0.28 GPa higher than pure acetone (Allan et al., 1999). The crystallization of acetone leads to extinction of the weak CT band, but is accompanied by the abrupt change in the λ_max2 position. At 1.39 GPa, λ_max1 = 266.8 nm while λ_max2 shifts about 27 nm and reaches λ_max2 = 328 nm. Compression to 1.93 GPa further shifts the bands to 269 and 330 nm for λ_max1 and λ_max2, respectively.

3.2. High-pressure solvates of ET(1)

The crystal structure of ET(1) at room temperature was first reported by Stadnicka et al. (2002), who revealed significant instability of the crystals. The quality of the red needle-like crystals of ET(1) depends on the temperature and humidity (Stadnicka et al., 2002). This degradation is manifested as a colour change from red to blue. The X-ray diffraction data, collected for the red crystals coated with silicone oil under ambient conditions, show that ET(1) zwitterions crystallize in the orthorhombic space group C222₁, forming a hydrate with a non-stoichiometric amount of water (5.78 molecules per structural unit). In this crystal structure, the torsion angle between the phenolate and the pyridinium ring is equal to 60.0 (2)° (Stadnicka et al., 2002). Such a conformation was also reported for protonated ET(1) in bi­phenyl-4-sulfonic and 4-amino­benzene­sulfonic salts (Wojtas et al., 2004).

Our attempts to obtain single crystals of ET(1) from different solvents at room temperature confirmed the previously reported challenges (Stadnicka et al., 2002), which we tackled by stabilizing the crystal phases under the strictly controlled thermodynamic conditions in the DAC. This prompted us to perform isochoric recrystallizations in a DAC (Katrusiak, 2008, 2019) aimed at the structural determination of ET(1) molecules in their solvation environment in the solid state, analogous to the solvatochromic effects observed in the solutions of methanol, ethanol and acetone for which we measured the absorption spectra under pressure.

The isochoric crystallization of the ET(1) in methanol at 0.57 GPa and 1.17 GPa yielded yellow single-crystal plates of the ET(1) tetra­methanol solvate, ET(1)·4CH₃OH. It is remarkable that these crystals and the ET(1) methanol solution are very similar in colour (Fig. 4), which can be an indication that the solvation spheres are very similar for the solution and the solvate. The ET(1)·4CH₃OH solvate crystallizes in the monoclinic system with the space group P2₁/n. One ET(1) molecule hydrogen bonded to four methanol (CH₃OH) molecules constitutes the asymmetric unit. At 0.57 GPa, the hydrogen bonds around the carbonyl oxygen O(1) can be represented by O(1)⋯H—O1m, O(1)⋯H—O4m, O(1)⋯H—O2m, in addition to the hydrogen bond between methanol molecules, O2m⋯H—O3m of 1.951 (18) Å. The solvate molecules are positioned on the (101) crystallographic plane, which separates the C—H⋯π bonded ET(1) molecules. There are two C—H⋯π aggregates present in ET(1)·4CH₃OH: (i) cyclomer of four ET(1) molecules with hydrogen bonds involving the lateral phenyl rings perpendicular to crystal direction [001]; and (ii) a chain of interlocking ET(1) molecules along the [101] direction linked by hydrogen bonds involving phenolate moieties and phenolate rings. The conformation of zwitterions of ET(1) is defined by the rotation of the N-phenolate ring, described by the torsion angles C1—N1—C14—C15′ (τ₁) and C1′—N1—C14—C15 (τ₁′). Additionally, the conformation of three phenyl substituents is described by the torsion angles C2—C3—C4—C5 (τ₂), C2′—C3—C4—C5′ (τ2′), C2—C1—C8—C13 (τ₃), N1—C1—C8—C9 (τ₃′), C2′—C1′—C8′—C13′ (τ₄) and N1—C1′—C8′—C9′ (τ₄′), as illustrated in Fig. 1 and detailed in Table 1

Figure 4 (a) Hydrogen bonds between ET(1) and four methanol molecules in the crystal structure of ET(1)·4CH3OH at 0.57 GPa. (b) Unit cell of ET(1)·4CH3OH viewed along crystal direction [100]. (c) Single crystal of ET(1)·4CH3OH grown in the DAC at 0.57 GPa.

At 1.17 GPa, the conformation of zwitterion ET(1) is retained except for minor changes in the torsion angles. The increased pressure tightens the voids around solvent molecules, particularly noticeable along the [010] direction which is ca 0.5 Å shorter compared with that at 0.57 GPa. The strong coupling between the pyridinium and phenolate ring in the methanol solvate is best represented by the short N(1)—C(14) and O(1)—C(17) bond distances. The N(1)—C(14) bond decreased from 1.437 (15) Å at 0.57 GPa to 1.41 (3) Å at 1.17 GPa, which is much shorter compared with other crystalline betaine dyes (Baran et al., 2001; Shekhovtsov et al., 2012; Schowner et al., 2018; Wojtas et al., 2006, 2004; Kurjatschij et al., 2010; Pike et al., 2018). At the same time, the C(17)—O(1) bonds of 1.306 (17) and 1.31 (3) Å at 0.57 and 1.17 GPa, respectively, are longer than those found in other solvates and shorter than the C(17)—O(1)H bond present in the salts of similar dyes. The conformation of ET(1) in this solvate confirms the delocalization of the negative charge at O(1), improving its hydrogen-acceptor capability. As presented in Table 2, the corresponding torsion angles τ₁ and τ₁′ are above 70° and become more open with higher pressure. The conjugation of the π-electrons in the betaine core is shown by the alignment of the apex p-phenyl substituent, with respect to the central N-phenolate ring, with τ₂ and τ₂′ of about 35°. The conformation of other phenyl substituents characterized by τ₃ and τ₃′ as well as τ₄ and τ₄′ values is strongly affected due to the presence of stacking aggregates and thus they assume a more twisted conformation with torsion angles above 50°.

Table 2
Conformation of the ET(1) zwitterions in different solvates under high pressure

	ET(1)·4CH3OH		ET(1)·4C2H5OH·H2O		ET(1)·6H2O
	0.57 GPa	1.17 GPa	0.24 GPa	0.76 GPa	0.22 GPa
τ1 (°)	75.9 (2)	72.5 (3)	65.6 (3)	48.3 (3)	57.1 (3)
τ1′ (°)	71.8 (2)	77.9 (3)	59.2 (3)	74.4 (4)	–
τ2 (°)	33.8 (2)	41.0 (2)	20.8 (2)	28.6 (4)	49.2 (3)
τ2′ (°)	35.4 (2)	32.6 (2)	34.3 (3)	36.4 (4)	–
τ3 (°)	45.8 (2)	48.7 (3)	51.6 (3)	36.4 (2)	40.2 (2)
τ3′ (°)	55.0 (2)	45.8 (2)	45.0 (2)	66.0 (3)	57.0 (3)
τ4 (°)	55.3 (1)	54.7 (3)	42.1 (2)	41.2 (2)	–
τ4′ (°)	58.4 (1)	60.0 (3)	53.1 (3)	53.2 (2)	–

The isochoric recrystallization of ET(1) at 0.24 GPa and 0.76 GPa from ethanol (C₂H₅OH) solution yielded red single crystals, again similar to the colour of the ET(1) solution in ethanol. The high-pressure X-ray diffraction experiments revealed that we obtained yet another solvate. This three-component compound ET(1)·4C₂H₅OH·H₂O crystallizes in the trigonal system with the space group R3c (Fig. 5). We emphasize that, owing to the limitations of the high-pressure technique and the complexity of the structure, the data collected did not allow us to unambiguously confirm the noncentrosymmetric nature of this solvate. However, with the aim of minimizing the deviation of the bond lengths and the size of the thermal vibration ellipsoids as well as the R₁ and R₂ parameters, we chose a symmetry without an inversion centre. The structure of ET(1)·4C₂H₅OH·H₂O is porous, resembling the solvates of ET(30), obtained from vapour diffusion crystallization of di­ethyl ether into solutions of chloro­form, di­chloro­methane, aceto­nitrile and 1-octanol (Pike et al., 2018). These solvates of ET(30) are also porous with disordered solvent molecules filling the channels extending along the [001] direction [see Fig. 5(a)]; however, all crystallize in the centrosymmetric space group R3c. The void analysis performed with the probing sphere radius of 1.40 Å (Olex2) of ET(1)·4C₂H₅OH·H₂O at 0.24 GPa shows that the channels have a minimum internal diameter of 4 Å and the largest spherical cavity of 7.2 Å across. In this solvate, the ET(1) molecules occupy only about 39.50% of the total crystal volume, which is unexpected as the high pressure usually favours a dense, close molecular packing. What is more, at 0.76 GPa the pores are still not eliminated with the void radius reduced only to 3.4 Å.

Figure 5 (a) Unit cell of ET(1)·4C2H5OH·H2O viewed along the [001] direction. (b) Asymmetric part of the unit cell in ET(1)·4C2H5OH·H2O with hydrogen bonds indicated. (c) Single crystal grown in the DAC at 0.24 GPa.

It is apparent that the packing arrangement in ET(1)·4C₂H₅OH·H₂O at high pressure originates from the strong hydrogen bonds with guest solvents and intermolecular edge-to-face C—H⋯π interactions formed between lateral phenyl rings, as well as the phenolate moiety and lateral phenyls. Although the ET(1) molecules do not form C—H⋯O bonds with aromatic protons, as was reported for ET(30) solvates (Pike et al., 2018), the stacking interactions similarly introduce a 120° angle between the C₂ central axis of the molecules, symmetrically related by a twofold rotation about its central core, producing a `trigonal node' and the hexagonal structure. Its framework is supported by hydrogen bonds between the carbonyl atom O(1) and solvent C₂H₅OH. The O1e—H⋯O2e—H⋯O(1)⋯H—O4e⋯H—O3e hydrogen bonds in the crystal structure are depicted in Fig. 5(b). The strongly disordered water molecules, located on special positions inside the cavities, do not form strong interactions with ET(1) and ethanol molecules.

In the ET(1)·4C₂H₅OH·H₂O solvate, the ET(1) molecule is more strongly conjugated than in the methanol solvate. This is shown by a flatter conformation of the ET(1) core, specifically connected to torsion angles τ₁ and τ₁′ both approximately 60°, and τ₂ and τ₂′ both around 30°, as detailed in Table 2. The flatter structure is more favourable for the π-electron delocalization within the ET(1) core. The conjugation between the rings can be further confirmed by the N(1)—C(14) bond length of 1.45 (2) Å which is not affected as the pressure changes from 0.24 to 0.76 GPa. In contrast, the O(1)—C(17) bond decreases from 1.323 (17) to 1.308 (6) Å, respectively. The alignment of the lateral phenyl substituents, indicated by the pairs of angles τ₃ and τ₃′, τ₄ and τ₄′, are all around 50°, showing that the ET(1) molecule adopts its conformation to its strong C—H⋯π bonds.

The successful high-pressure crystallization from the acetone solution at 0.22 GPa (see Fig. 6) yielded another solvate. The single crystal of hexahydrate ET(1)·6H₂O is isostructural to the previously determined hydrate ET(1)·5.78H₂O obtained at room temperature and pressure. Both these crystals are orthorhombic with the space group C222₁. The ET(1) molecule in ET(1)·6H₂O is located on a twofold axis along the C₂ axis of its core. The ET(1) molecules are stacked in a distinct antiparallel mode in columns along the crystal direction [001]. This stacking involves the central pyridinium ring and the core phenyl moiety of the neighbouring molecule related by the symmetry of twofold axis, but the mean planes of these rings are inclined by 24.8 (2)°. Nonetheless, the shortest contacts between atoms C(3) and C(5) of these rings are 3.06 (1) Å long and reassemble pancake bonds. These contacts affect the position of p-phenyls, twisting their conformation at 0.22 GPa compared with the ET(1)·5.78H₂O structure under normal conditions. The disordered water molecules are located along the channels in the [001] crystal direction between the π-stacked columns and do not form any short contacts with the ET(1) molecule. The solvent-accessible channels, including the largest spherical voids of 2.60 Å in radius, occupy 47.3% of the crystal volume. This allows the guest solvent molecules to be easily transported within the crystal, which is manifested by the non-stoichiometric number of guest molecules in the crystals exposed to the room environment. Thus, the higher water content at high pressure, confirmed by slightly larger unit-cell dimensions of the high-pressure hydrate, results from the confined environment inside the DAC, enforcing the guest molecules to remain in their most favoured positions in the crystal structure.

Figure 6 (a) ET(1)·6H2O crystal structure with water-filled pores along the [001] direction. (b) Single crystal of ET(1)·6H2O in the DAC at 0.22 GPa. (c) The conformation of ET(1) molecule in ET(1)·6H2O.

In ET(1)·6H₂O under high pressure, the molecular structure of ET(1) is more planar, with an enhanced π-electron delocalization across the molecule. This planarity is particularly reflected in torsion angles τ₁ = 57.1 (3)°, τ₂ = 49.2 (3)°, τ₃ = 40.2 (2)° and τ₄ = 57.0 (3)°, indicating a significantly narrower alignment of the phenyl rings with the central pyridinium ring, facilitating a strong conjugation within the ET(1) core. Similarly, the C(17)—O(1) and N(1)—C(14) bond lengths are 1.252 and 1.499 Å, respectively, which is much shorter than those observed under ambient conditions and in ET(1)·6H₂O.

Based on the crystallographic data, the ET(1) molecules adopt the most twisted conformation in methanol and are most planar in the water solvate. This result is consistent with the quantum mechanical calculations by Bartkowiak & Lipiński (1998), suggesting an increase in the molecular dipole moment as angle τ₁ increases towards 90°. Various possible contributions to the conformational changes include the strain from CH⋯π bonded aggregates, the formation of strong hydrogen-bonds and the intrusion of small solvate molecules into the interstitial spaces between phenyl rings. The close molecular packing in the ET(1)·4CH₃OH solvate can be attributed to the strong interaction formed between betaine and the solvent molecules, depicted in the interaction mapped in Fig. 7 (Macrae et al., 2008). The relationship between the conformational twist of ET(1) and its increasing polarity is corroborated by electrostatic potential calculations performed in CrystalExplorer (Spackman et al., 2021), which indicate the highest values in the methanol solvate. Another characteristic feature of the ET(1) zwitterions is the bending angle measured between the centroids of the core rings. It differs between 180° for the hydrate (where the core rings lie on a twofold axis), 179° for ET(1)·4C₂H₅OH·H₂O and 175.5° in ET(1)·4CH₃OH; the departure of this angle from 180° can be associated with different interactions on both sites of the molecules, which is confirmed by the increased departure for the high-pressure structures. This angular parameter illustrates the effect of the crystal packing and the surrounding interactions on the molecular dimensions.

Figure 7 Full interaction maps in ET(1)·4CH3OH, ET(1)·4C2H5OH·H2O and ET(1)·6H2O solvates and the electrostatic potential plots mapped onto electron density isosurfaces (0.008 e a.u.^−3) performed in CrystalExplorer calculated at the B3LYP/6-(d,p) level of theory.

4. Conclusions

In this study, we explored the solvatochromic behaviour of Reichardt's dye, ET(1), at high-pressure. Through complementary experimental methods involving high-pressure single-crystal X-ray diffraction and high-pressure UV–Vis spectroscopy, we elucidated the intricate connection between solvatochromism and solvatomorphism for the prototypic representative of these important dyes. The distinctive solvatochromic shifts observed for ET(1) in different solvent environments – methanol, ethanol and acetone – underpin the complex interplay between solvent polarity, hydrogen bonding, molecular conformation and crystal packing. The significant influence of the solvation process on the nucleation of the crystal phases highlights the role of the molecular structure and solute–solvent interactions. The observed piezo-solvatochromic effects contribute to a deeper understanding of molecular chemistry under constrained conditions, shedding light on the stabilization mechanisms of the ET(1) zwitterionic ground state. We have established that (1) Reichardt's dye, ET(1), favours crystallization in the form of solvates, which show crystal colours similar to their respective solutions; and (2) the intramolecular interactions include, aside from the hydrogen bonds O(1)⋯HO to the solvate molecules and CH⋯π to the neighbouring ET(1) molecules, also the van der Waals contacts to the solvent molecules that penetrate the hollows of the ET(1) molecular surface between the phenyl ring. This latter type of contact is the shortest for the smallest (water and methanol) molecules. It appears particularly important because it affects the inclinations of the phenyls to the core rings, which in turn affects the conjugation of the π electrons, structure and the absorption. The alcohol and water molecules occupy independent sites in the structure, so they interact differently with the ET(1) molecules: ethanol or methanol molecules interact directly with the solvatochromic centres, while the water molecules are weakly associated by dispersive forces, so their effect is marginal. The multiple solvation is not very common – our search of the Cambridge Structural Database (Version 5.45) revealed only 1949 and 475 fourfold methanol or ethanol structures, respectively. What is more, to date, ET(1)·4CH₃OH and ET(1)·4C₂H₅OH·H₂O are the first structures of organic molecules containing no metal atoms and are solvated by four alcohol molecules. It is remarkable that this multiple solvation occurs for the solvatochromic compounds, where the molecular surfaces form highly selective pockets that are preferential for the solvate molecules with hydro­philic (hydroxyl) and hydro­phobic (aliphatic) residues. These host–guest contacts can be associated with the electrostatic and hydrogen bonds to the zwitterionic sites on one hand, and with the dispersion forces and weak CH⋯C and CH⋯π bonds to the phenyl substituents on the other. The solvatochromic properties can be connected to such a preferential docking of specific solvates, which diminishes the interference of the moisture and the presence of water in the solution.

The implications of this study are far-reaching, particularly in the realm of materials science and nonlinear optoelectronics. The ability to tune the optical properties of Reichardt's dyes based on pressure opens new avenues for developing advanced photonic materials and pressure-sensitive molecular sensors. Additionally, the insights gained from the solvation mechanism of ET(1) provide basic information about its structure, conformation, interactions and solvation capabilities that are indispensable for the rational design and synthesis of novel molecular dyes with tailored solvatochromic properties for specific applications. The study of solvatochromic shifts under varying pressure conditions opens up new avenues for understanding solvent-mediated effects in molecular systems. The pressure-dependent solvatochromism not only provides a deeper insight into the solute–solvent dynamics, but also paves the way for exploring potential applications in pressure-sensitive molecular sensors and materials science, particularly in the development of advanced photonic materials.

Supporting information

Computing details

4-(2,4,6-triphenylpyridinium-1-yl)-phenolate hexahydrate (et1_acetone_0_22gpa)

Crystal data

C29H21NO·6(O)	Dx = 1.235 Mg m^−3
Mr = 495.47	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, C2221	Cell parameters from 524 reflections
a = 15.311 (4) Å	θ = 2.5–26.4°
b = 23.948 (6) Å	µ = 0.09 mm^−1
c = 7.27 (2) Å	T = 293 K
V = 2664 (9) Å^3	Block, clear red
Z = 4	0.22 × 0.14 × 0.1 mm
F(000) = 1032

Data collection

New Xcalibur, EosS2 diffractometer	242 reflections with I > 2σ(I)
ω scans	Rint = 0.210
Absorption correction: gaussian	θmax = 26.3°, θmin = 1.6°
Tmin = 0.965, Tmax = 0.981	h = −18→16
6172 measured reflections	k = −29→28
526 independent reflections	l = −1→1

Refinement

Refinement on F^2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.2P)^2] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.137	(Δ/σ)max < 0.001
wR(F^2) = 0.378	Δρmax = 0.21 e Å^−3
S = 1.28	Δρmin = −0.13 e Å^−3
526 reflections	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
149 parameters	Extinction coefficient: 0.18 (7)
501 restraints	Absolute structure: Flack x determined using 49 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
Hydrogen site location: inferred from neighbouring sites	Absolute structure parameter: 10.0 (10)

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C4	0.000000	−0.0205 (14)	0.750000	0.099 (17)
N1	0.000000	0.1555 (10)	0.750000	0.08 (2)
C1	0.0768 (10)	0.1284 (8)	0.717 (8)	0.073 (18)
C14	0.000000	0.2162 (13)	0.750000	0.07 (2)
C2	0.0770 (9)	0.0712 (8)	0.719 (8)	0.07 (2)
H2	0.129078	0.052205	0.699256	0.082*
C8	0.1632 (10)	0.1569 (9)	0.728 (8)	0.079 (18)
C13	0.1877 (12)	0.1959 (9)	0.860 (7)	0.11 (2)
H13	0.148808	0.206124	0.951996	0.126*
C12	0.2705 (13)	0.2197 (8)	0.854 (7)	0.10 (2)
H12	0.286952	0.245799	0.941701	0.118*
C11	0.3287 (10)	0.2044 (10)	0.716 (8)	0.12 (2)
H11	0.384073	0.220339	0.711419	0.145*
C10	0.3041 (11)	0.1654 (10)	0.584 (7)	0.09 (2)
H10	0.343051	0.155203	0.491430	0.106*
C9	0.2214 (12)	0.1416 (8)	0.590 (7)	0.10 (2)
H9	0.204907	0.115527	0.501722	0.118*
C3	0.000000	0.0407 (12)	0.750000	0.09 (2)
C17	0.000000	0.3359 (16)	0.750000	0.12 (3)
C5	−0.0610 (18)	−0.0515 (11)	0.648 (5)	0.112 (11)
H5	−0.102393	−0.032644	0.577638	0.134*
O1	0.000000	0.3885 (12)	0.750000	0.18 (4)
C6	−0.0613 (18)	−0.1098 (11)	0.648 (6)	0.128 (12)
H6	−0.102557	−0.129168	0.578765	0.153*
C7	0.000000	−0.1385 (16)	0.750000	0.131 (15)
H7	0.000000	−0.177331	0.750000	0.157*
O2W	0.309 (3)	0.0729 (17)	1.075 (16)	0.249 (18)*
O3W	0.292 (3)	0.037 (2)	0.72 (2)	0.126 (17)*	0.5
O4W	0.264 (3)	0.000 (2)	0.765 (18)	0.16 (2)*	0.5
O1W	0.4613 (19)	0.0562 (13)	0.611 (16)	0.202 (17)*
C16	0.0284 (14)	0.2462 (8)	0.597 (3)	0.07 (2)
H16	0.046778	0.227065	0.492080	0.087*
C15	0.0298 (17)	0.3052 (9)	0.598 (3)	0.09 (2)
H15	0.050896	0.324122	0.495526	0.112*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C4	0.11 (2)	0.077 (12)	0.11 (5)	0.000	0.00 (2)	0.000
N1	0.070 (10)	0.065 (11)	0.10 (6)	0.000	0.01 (2)	0.000
C1	0.074 (9)	0.070 (9)	0.08 (5)	0.011 (7)	0.002 (18)	0.003 (19)
C14	0.037 (17)	0.065 (11)	0.09 (6)	0.000	−0.01 (3)	0.000
C2	0.066 (11)	0.069 (9)	0.07 (6)	0.012 (8)	−0.01 (3)	0.00 (2)
C8	0.074 (10)	0.082 (14)	0.08 (5)	0.005 (9)	0.002 (18)	0.00 (2)
C13	0.083 (12)	0.13 (2)	0.10 (6)	−0.004 (12)	−0.01 (2)	−0.03 (3)
C12	0.072 (13)	0.131 (19)	0.09 (6)	0.004 (13)	−0.03 (2)	−0.02 (3)
C11	0.101 (19)	0.15 (3)	0.11 (6)	−0.014 (16)	0.01 (2)	−0.02 (3)
C10	0.070 (11)	0.100 (19)	0.10 (6)	0.021 (11)	0.00 (2)	0.00 (3)
C9	0.076 (12)	0.116 (18)	0.10 (6)	0.013 (12)	0.01 (2)	−0.02 (2)
C3	0.083 (14)	0.077 (11)	0.10 (6)	0.000	0.01 (3)	0.000
C17	0.19 (4)	0.065 (15)	0.09 (7)	0.000	−0.03 (4)	0.000
C5	0.119 (15)	0.105 (11)	0.11 (2)	−0.015 (9)	0.005 (14)	−0.007 (12)
O1	0.34 (4)	0.065 (14)	0.14 (11)	0.000	0.03 (6)	0.000
C6	0.147 (15)	0.111 (11)	0.126 (19)	−0.011 (10)	−0.011 (13)	−0.013 (12)
C7	0.138 (18)	0.124 (16)	0.13 (2)	0.000	0.002 (13)	0.000
C16	0.054 (15)	0.071 (11)	0.09 (6)	−0.015 (11)	−0.01 (2)	0.000 (14)
C15	0.11 (2)	0.072 (11)	0.10 (7)	0.002 (13)	−0.03 (3)	0.006 (15)

Geometric parameters (Å, º)

C4—C3	1.47 (4)	C11—H11	0.9300
C4—C5	1.406 (18)	C11—C10	1.3900
C4—C5^i	1.406 (18)	C10—H10	0.9300
N1—C1	1.36 (2)	C10—C9	1.3900
N1—C1^i	1.36 (2)	C9—H9	0.9300
N1—C14	1.46 (4)	C17—O1	1.26 (4)
C1—C2	1.368 (18)	C17—C15	1.403 (18)
C1—C8	1.49 (2)	C17—C15^i	1.403 (18)
C14—C16^i	1.395 (17)	C5—H5	0.9300
C14—C16	1.395 (17)	C5—C6	1.394 (19)
C2—H2	0.9300	C6—H6	0.9300
C2—C3	1.405 (18)	C6—C7	1.381 (19)
C8—C13	1.3900	C7—H7	0.9300
C8—C9	1.3900	O3W—O4W	1.02 (7)
C13—H13	0.9300	C16—H16	0.9300
C13—C12	1.3900	C16—C15	1.413 (19)
C12—H12	0.9300	C15—H15	0.9300
C12—C11	1.3900
C5—C4—C3	121.9 (13)	C11—C10—H10	120.0
C5^i—C4—C3	121.9 (13)	C11—C10—C9	120.0
C5—C4—C5^i	116 (3)	C9—C10—H10	120.0
C1^i—N1—C1	123 (2)	C8—C9—H9	120.0
C1—N1—C14	118.4 (12)	C10—C9—C8	120.0
C1^i—N1—C14	118.4 (12)	C10—C9—H9	120.0
N1—C1—C2	118.4 (14)	C2—C3—C4	121.4 (13)
N1—C1—C8	123 (2)	C2^i—C3—C4	121.4 (13)
C2—C1—C8	117.2 (13)	C2—C3—C2^i	117 (3)
C16^i—C14—N1	120.9 (13)	O1—C17—C15^i	121.6 (14)
C16—C14—N1	120.9 (13)	O1—C17—C15	121.6 (14)
C16^i—C14—C16	118 (3)	C15—C17—C15^i	117 (3)
C1—C2—H2	119.3	C4—C5—H5	119.0
C1—C2—C3	121.4 (15)	C6—C5—C4	122.0 (16)
C3—C2—H2	119.3	C6—C5—H5	119.0
C13—C8—C1	126 (3)	C5—C6—H6	120.1
C13—C8—C9	120.0	C7—C6—C5	119.7 (19)
C9—C8—C1	114 (3)	C7—C6—H6	120.1
C8—C13—H13	120.0	C6^i—C7—C6	120 (3)
C8—C13—C12	120.0	C6^i—C7—H7	119.9
C12—C13—H13	120.0	C6—C7—H7	119.9
C13—C12—H12	120.0	C14—C16—H16	119.6
C11—C12—C13	120.0	C14—C16—C15	120.8 (15)
C11—C12—H12	120.0	C15—C16—H16	119.6
C12—C11—H11	120.0	C17—C15—C16	121.7 (16)
C10—C11—C12	120.0	C17—C15—H15	119.2
C10—C11—H11	120.0	C16—C15—H15	119.2
C4—C5—C6—C7	0 (2)	C2—C1—C8—C9	57 (3)
N1—C1—C2—C3	1 (2)	C8—C1—C2—C3	166 (6)
N1—C1—C8—C13	40 (6)	C8—C13—C12—C11	0.0
N1—C1—C8—C9	−139 (4)	C13—C8—C9—C10	0.0
N1—C14—C16—C15	−178.9 (18)	C13—C12—C11—C10	0.0
C1^i—N1—C1—C2	−0.6 (11)	C12—C11—C10—C9	0.0
C1^i—N1—C1—C8	−164 (6)	C11—C10—C9—C8	0.0
C1—N1—C14—C16^i	−123 (3)	C9—C8—C13—C12	0.0
C1—N1—C14—C16	57 (3)	C3—C4—C5—C6	−179.9 (11)
C1^i—N1—C14—C16^i	57 (3)	C5^i—C4—C3—C2	49 (4)
C1^i—N1—C14—C16	−123 (3)	C5—C4—C3—C2^i	49 (4)
C1—C2—C3—C4	179.4 (12)	C5^i—C4—C3—C2^i	−131 (4)
C1—C2—C3—C2^i	−0.6 (12)	C5—C4—C3—C2	−131 (4)
C1—C8—C13—C12	−180 (3)	C5^i—C4—C5—C6	0.1 (11)
C1—C8—C9—C10	180 (3)	C5—C6—C7—C6^i	0.1 (11)
C14—N1—C1—C2	179.4 (11)	O1—C17—C15—C16	−178.9 (18)
C14—N1—C1—C8	16 (6)	C16^i—C14—C16—C15	1.1 (18)
C14—C16—C15—C17	−2 (4)	C15^i—C17—C15—C16	1.1 (18)
C2—C1—C8—C13	−123.5 (16)

Symmetry code: (i) −x, y, −z+3/2.

4-(2,4,6-triphenylpyridinium-1-yl)-phenolate tetramethanol solvate (et1_meoh_0_57gpa)

Crystal data

C29H21NO·4(CH4O)	F(000) = 1128
Mr = 527.63	Dx = 1.276 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.4704 (11) Å	Cell parameters from 3200 reflections
b = 19.80 (3) Å	θ = 2.2–25.1°
c = 13.3135 (15) Å	µ = 0.09 mm^−1
β = 95.819 (9)°	T = 293 K
V = 2746 (4) Å^3	Block, clear orangish yellow
Z = 4	0.39 × 0.12 × 0.10 mm

Data collection

New Xcalibur, EosS2 diffractometer	801 reflections with I > 2σ(I)
Detector resolution: 8.0169 pixels mm^-1	Rint = 0.142
ω scans	θmax = 26.4°, θmin = 4.6°
Absorption correction: analytical CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −14→14
Tmin = 0.999, Tmax = 0.999	k = −5→5
22964 measured reflections	l = −18→17
1643 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.086	w = 1/[σ^2(Fo^2) + (0.1734P)^2 + 1.5201P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.296	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.16 e Å^−3
1643 reflections	Δρmin = −0.17 e Å^−3
358 parameters	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
618 restraints

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.4112 (5)	0.3744 (10)	0.1763 (4)	0.079 (11)
C4	1.2172 (8)	0.1520 (10)	0.4160 (7)	0.041 (9)
N1	0.8507 (5)	0.2380 (9)	0.3197 (4)	0.052 (7)
C10'	0.7921 (8)	0.4173 (12)	0.5098 (7)	0.067 (9)
H10'	0.775817	0.460934	0.485869	0.080*
C9'	0.8328 (11)	0.3698 (10)	0.4452 (8)	0.056 (8)
H9'	0.842013	0.381787	0.378796	0.068*
C5'	1.3144 (7)	0.1917 (11)	0.4630 (5)	0.054 (10)
H5'	1.296750	0.236392	0.478346	0.065*
C6'	1.4364 (9)	0.1670 (11)	0.4878 (8)	0.056 (11)
H6'	1.500672	0.193766	0.520601	0.067*
C13'	0.8454 (8)	0.2881 (12)	0.5765 (6)	0.063 (10)
H13'	0.864053	0.244911	0.601393	0.076*
C16	0.5104 (7)	0.2931 (11)	0.2844 (6)	0.057 (12)
H16	0.432630	0.283962	0.309687	0.069*
C17	0.5147 (7)	0.3407 (11)	0.2082 (6)	0.060 (12)
C16'	0.6313 (6)	0.3512 (12)	0.1705 (6)	0.066 (10)
H16'	0.636070	0.382821	0.119353	0.079*
C15'	0.7405 (7)	0.3165 (10)	0.2060 (6)	0.051 (4)
H15'	0.817636	0.324081	0.178833	0.062*
C2M	0.8494 (18)	0.0571 (15)	0.4426 (12)	0.141 (11)
H2MA	0.799685	0.043865	0.381193	0.211*
H2MB	0.844372	0.022636	0.492672	0.211*
H2MC	0.937281	0.063383	0.430019	0.211*
C11'	0.7744 (13)	0.4030 (12)	0.6085 (9)	0.067 (10)
H11'	0.745938	0.434944	0.652420	0.080*
C14	0.7334 (6)	0.2710 (11)	0.2818 (5)	0.051 (7)
O1M	1.0539 (9)	−0.0002 (16)	0.2315 (7)	0.13 (3)
H1M	1.087951	−0.035586	0.251740	0.200*
C3	1.0891 (6)	0.1784 (10)	0.3857 (5)	0.042 (9)
C6	1.3665 (8)	0.0592 (12)	0.4148 (7)	0.066 (10)
H6	1.384803	0.014648	0.399652	0.079*
C5	1.2450 (9)	0.0862 (10)	0.3907 (7)	0.049 (9)
H5	1.181075	0.059656	0.356942	0.059*
C1	0.9005 (7)	0.1871 (10)	0.2649 (5)	0.047 (7)
C15	0.6184 (6)	0.2596 (12)	0.3226 (5)	0.057 (12)
H15	0.614993	0.229351	0.375733	0.069*
O4M	1.0025 (10)	0.4717 (17)	0.2932 (7)	0.19 (3)
H4M	1.049596	0.440925	0.278350	0.281*
O3M	1.1729 (10)	0.3815 (14)	0.2153 (10)	0.15 (2)
H3M	1.242220	0.379692	0.191722	0.221*
C13	0.8928 (9)	0.1551 (14)	0.0831 (5)	0.075 (5)
H13	0.977611	0.169366	0.084494	0.091*
C1'	0.9153 (6)	0.2547 (11)	0.4121 (5)	0.043 (8)
C9	0.7032 (8)	0.1405 (13)	0.1654 (7)	0.068 (14)
H9	0.659031	0.144866	0.222287	0.082*
C7	1.4593 (12)	0.1013 (11)	0.4621 (9)	0.061 (11)
H7	1.541652	0.084121	0.477291	0.073*
C2	1.0173 (6)	0.1593 (13)	0.2959 (5)	0.056 (10)
H2	1.050244	0.126501	0.255758	0.067*
C8	0.8294 (7)	0.1627 (12)	0.1679 (5)	0.059 (5)
C2'	1.0329 (6)	0.2265 (10)	0.4422 (5)	0.045 (9)
H2'	1.076420	0.240417	0.503079	0.054*
C11	0.7077 (11)	0.1042 (17)	−0.0048 (8)	0.107 (5)
H11	0.666672	0.083799	−0.062259	0.128*
C1M	0.9624 (14)	−0.013 (2)	0.1558 (9)	0.09 (3)
H1MA	0.994756	−0.045028	0.109940	0.137*
H1MB	0.938433	0.027691	0.120477	0.137*
H1MC	0.888720	−0.032260	0.182860	0.137*
C12	0.8324 (11)	0.1262 (15)	−0.0052 (7)	0.101 (5)
H12	0.875330	0.121960	−0.062712	0.121*
C3M	1.1367 (15)	0.3209 (14)	0.2369 (12)	0.12 (2)
H3MA	1.149625	0.291062	0.181992	0.182*
H3MB	1.047434	0.321407	0.247571	0.182*
H3MC	1.186425	0.305453	0.297078	0.182*
O2M	0.8040 (9)	0.1139 (13)	0.4752 (7)	0.125 (11)
H2M	0.812095	0.114136	0.537071	0.187*
C4M	0.9135 (15)	0.479 (2)	0.2245 (11)	0.12 (3)
H4MA	0.938911	0.460859	0.162671	0.179*
H4MB	0.894372	0.526195	0.215757	0.179*
H4MC	0.838565	0.455640	0.242083	0.179*
C10	0.6436 (10)	0.1118 (14)	0.0786 (7)	0.077 (16)
H10	0.558718	0.097604	0.076868	0.092*
C12'	0.8022 (13)	0.3376 (11)	0.6366 (9)	0.069 (11)
H12'	0.790725	0.325677	0.702688	0.083*
C8'	0.8604 (9)	0.3049 (10)	0.4763 (6)	0.045 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.052 (3)	0.09 (4)	0.090 (4)	0.003 (6)	0.003 (2)	−0.007 (7)
C4	0.050 (4)	0.02 (3)	0.054 (5)	−0.002 (7)	0.018 (3)	0.000 (9)
N1	0.051 (3)	0.06 (2)	0.051 (3)	−0.002 (6)	0.012 (2)	−0.014 (6)
C10'	0.080 (5)	0.03 (3)	0.085 (5)	0.009 (12)	0.006 (5)	−0.024 (10)
C9'	0.081 (7)	0.03 (2)	0.057 (5)	0.014 (11)	0.004 (5)	−0.006 (8)
C5'	0.057 (4)	0.04 (3)	0.068 (5)	−0.006 (8)	0.011 (3)	−0.018 (10)
C6'	0.053 (5)	0.05 (3)	0.065 (6)	−0.010 (9)	0.007 (4)	−0.007 (11)
C13'	0.087 (5)	0.05 (3)	0.057 (4)	0.033 (12)	0.022 (4)	−0.001 (8)
C16	0.047 (4)	0.05 (4)	0.075 (5)	−0.011 (8)	0.021 (3)	−0.008 (10)
C17	0.052 (4)	0.07 (4)	0.059 (4)	−0.015 (7)	0.007 (3)	−0.005 (9)
C16'	0.052 (4)	0.09 (3)	0.060 (4)	0.002 (7)	0.015 (3)	0.007 (9)
C15'	0.050 (3)	0.049 (12)	0.056 (4)	−0.007 (6)	0.015 (3)	−0.015 (6)
C2M	0.147 (12)	0.15 (3)	0.129 (11)	−0.006 (17)	0.039 (9)	0.025 (16)
C11'	0.069 (6)	0.05 (3)	0.085 (6)	0.013 (14)	0.013 (5)	−0.029 (11)
C14	0.049 (3)	0.06 (2)	0.047 (4)	−0.004 (7)	0.013 (3)	−0.015 (8)
O1M	0.153 (8)	0.06 (8)	0.177 (8)	−0.062 (15)	−0.057 (6)	0.047 (17)
C3	0.051 (3)	0.03 (3)	0.050 (4)	0.002 (7)	0.012 (3)	0.002 (7)
C6	0.065 (5)	0.04 (3)	0.099 (6)	0.012 (10)	0.012 (4)	−0.003 (12)
C5	0.063 (5)	0.02 (3)	0.062 (6)	0.004 (8)	0.013 (4)	−0.009 (10)
C1	0.053 (4)	0.04 (2)	0.048 (4)	−0.004 (7)	0.011 (3)	−0.002 (7)
C15	0.050 (4)	0.06 (4)	0.063 (4)	−0.009 (7)	0.012 (3)	−0.009 (9)
O4M	0.168 (9)	0.25 (9)	0.145 (8)	0.006 (17)	0.028 (5)	0.010 (15)
O3M	0.078 (6)	0.18 (6)	0.190 (10)	0.031 (14)	0.058 (5)	0.074 (17)
C13	0.094 (5)	0.075 (13)	0.057 (4)	0.010 (8)	0.006 (3)	0.003 (6)
C1'	0.048 (3)	0.03 (2)	0.057 (4)	−0.008 (7)	0.012 (3)	−0.011 (7)
C9	0.066 (4)	0.04 (4)	0.092 (6)	−0.001 (9)	−0.003 (4)	−0.019 (10)
C7	0.068 (6)	0.05 (3)	0.070 (7)	0.004 (10)	0.018 (4)	0.008 (12)
C2	0.045 (4)	0.06 (3)	0.066 (4)	0.004 (8)	0.009 (3)	−0.019 (9)
C8	0.063 (4)	0.056 (13)	0.058 (4)	0.003 (7)	0.002 (3)	−0.008 (6)
C2'	0.051 (4)	0.03 (3)	0.052 (4)	−0.005 (8)	0.005 (3)	−0.014 (8)
C11	0.124 (6)	0.099 (13)	0.090 (5)	0.004 (8)	−0.024 (5)	−0.014 (8)
C1M	0.133 (10)	0.03 (9)	0.107 (8)	0.005 (18)	−0.005 (6)	0.020 (16)
C12	0.131 (6)	0.097 (13)	0.073 (5)	0.004 (8)	0.007 (5)	−0.015 (8)
C3M	0.095 (10)	0.18 (6)	0.095 (8)	−0.01 (2)	0.025 (7)	0.010 (18)
O2M	0.096 (5)	0.17 (3)	0.107 (6)	0.009 (12)	−0.003 (5)	0.020 (11)
C4M	0.115 (10)	0.10 (10)	0.143 (12)	−0.018 (19)	0.017 (7)	0.08 (2)
C10	0.088 (6)	0.03 (5)	0.104 (6)	−0.005 (11)	−0.023 (4)	−0.010 (11)
C12'	0.087 (8)	0.05 (3)	0.071 (7)	0.019 (13)	0.036 (6)	−0.014 (9)
C8'	0.047 (4)	0.03 (2)	0.060 (5)	0.004 (9)	0.009 (4)	−0.005 (7)

Geometric parameters (Å, º)

O1—C17	1.306 (17)	C6—H6	0.9300
C4—C5'	1.384 (13)	C6—C5	1.387 (12)
C4—C3	1.458 (13)	C6—C7	1.381 (14)
C4—C5	1.384 (16)	C5—H5	0.9300
N1—C14	1.437 (15)	C1—C2	1.366 (13)
N1—C1	1.376 (16)	C1—C8	1.504 (12)
N1—C1'	1.383 (10)	C15—H15	0.9300
C10'—H10'	0.9300	O4M—H4M	0.8200
C10'—C9'	1.372 (14)	O4M—C4M	1.246 (12)
C10'—C11'	1.376 (12)	O3M—H3M	0.8200
C9'—H9'	0.9300	O3M—C3M	1.30 (2)
C9'—C8'	1.371 (15)	C13—H13	0.9300
C5'—H5'	0.9300	C13—C8	1.375 (10)
C5'—C6'	1.376 (12)	C13—C12	1.400 (13)
C6'—H6'	0.9300	C1'—C2'	1.374 (11)
C6'—C7	1.374 (16)	C1'—C8'	1.466 (17)
C13'—H13'	0.9300	C9—H9	0.9300
C13'—C12'	1.371 (14)	C9—C8	1.390 (12)
C13'—C8'	1.399 (11)	C9—C10	1.379 (12)
C16—H16	0.9300	C7—H7	0.9300
C16—C17	1.388 (14)	C2—H2	0.9300
C16—C15	1.365 (12)	C2'—H2'	0.9300
C17—C16'	1.381 (10)	C11—H11	0.9300
C16'—H16'	0.9300	C11—C12	1.377 (13)
C16'—C15'	1.376 (12)	C11—C10	1.363 (12)
C15'—H15'	0.9300	C1M—H1MA	0.9600
C15'—C14	1.361 (13)	C1M—H1MB	0.9600
C2M—H2MA	0.9600	C1M—H1MC	0.9600
C2M—H2MB	0.9600	C12—H12	0.9300
C2M—H2MC	0.9600	C3M—H3MA	0.9600
C2M—O2M	1.31 (2)	C3M—H3MB	0.9600
C11'—H11'	0.9300	C3M—H3MC	0.9600
C11'—C12'	1.372 (16)	O2M—H2M	0.8200
C14—C15	1.389 (9)	C4M—H4MA	0.9600
O1M—H1M	0.8200	C4M—H4MB	0.9600
O1M—C1M	1.344 (12)	C4M—H4MC	0.9600
C3—C2	1.398 (10)	C10—H10	0.9300
C3—C2'	1.382 (14)	C12'—H12'	0.9300
C5'—C4—C3	122.4 (14)	C16—C15—H15	120.2
C5'—C4—C5	118.8 (12)	C14—C15—H15	120.2
C5—C4—C3	118.7 (12)	C4M—O4M—H4M	109.5
C1—N1—C14	120.2 (8)	C3M—O3M—H3M	109.5
C1—N1—C1'	118.0 (9)	C8—C13—H13	119.4
C1'—N1—C14	121.8 (12)	C8—C13—C12	121.3 (11)
C9'—C10'—H10'	118.7	C12—C13—H13	119.4
C9'—C10'—C11'	122.5 (18)	N1—C1'—C8'	119.7 (9)
C11'—C10'—H10'	118.7	C2'—C1'—N1	120.4 (11)
C10'—C9'—H9'	119.2	C2'—C1'—C8'	119.9 (8)
C8'—C9'—C10'	121.5 (14)	C8—C9—H9	120.1
C8'—C9'—H9'	119.2	C10—C9—H9	120.1
C4—C5'—H5'	119.1	C10—C9—C8	119.9 (9)
C6'—C5'—C4	121.9 (16)	C6'—C7—C6	123.5 (16)
C6'—C5'—H5'	119.1	C6'—C7—H7	118.2
C5'—C6'—H6'	121.3	C6—C7—H7	118.2
C7—C6'—C5'	117.3 (16)	C3—C2—H2	118.8
C7—C6'—H6'	121.3	C1—C2—C3	122.5 (13)
C12'—C13'—H13'	121.3	C1—C2—H2	118.8
C12'—C13'—C8'	117.5 (16)	C13—C8—C1	120.1 (8)
C8'—C13'—H13'	121.3	C13—C8—C9	118.9 (10)
C17—C16—H16	119.5	C9—C8—C1	120.6 (7)
C15—C16—H16	119.5	C3—C2'—H2'	118.7
C15—C16—C17	121.0 (8)	C1'—C2'—C3	122.6 (8)
O1—C17—C16	119.8 (8)	C1'—C2'—H2'	118.7
O1—C17—C16'	122.7 (14)	C12—C11—H11	119.6
C16'—C17—C16	117.6 (11)	C10—C11—H11	119.6
C17—C16'—H16'	118.9	C10—C11—C12	120.9 (14)
C15'—C16'—C17	122.3 (13)	O1M—C1M—H1MA	109.5
C15'—C16'—H16'	118.9	O1M—C1M—H1MB	109.5
C16'—C15'—H15'	120.7	O1M—C1M—H1MC	109.5
C14—C15'—C16'	118.6 (8)	H1MA—C1M—H1MB	109.5
C14—C15'—H15'	120.7	H1MA—C1M—H1MC	109.5
H2MA—C2M—H2MB	109.5	H1MB—C1M—H1MC	109.5
H2MA—C2M—H2MC	109.5	C13—C12—H12	120.8
H2MB—C2M—H2MC	109.5	C11—C12—C13	118.3 (11)
O2M—C2M—H2MA	109.5	C11—C12—H12	120.8
O2M—C2M—H2MB	109.5	O3M—C3M—H3MA	109.5
O2M—C2M—H2MC	109.5	O3M—C3M—H3MB	109.5
C10'—C11'—H11'	122.9	O3M—C3M—H3MC	109.5
C12'—C11'—C10'	114.2 (19)	H3MA—C3M—H3MB	109.5
C12'—C11'—H11'	122.9	H3MA—C3M—H3MC	109.5
C15'—C14—N1	116.9 (7)	H3MB—C3M—H3MC	109.5
C15'—C14—C15	120.8 (11)	C2M—O2M—H2M	109.5
C15—C14—N1	122.2 (12)	O4M—C4M—H4MA	109.5
C1M—O1M—H1M	109.5	O4M—C4M—H4MB	109.5
C2—C3—C4	122.7 (11)	O4M—C4M—H4MC	109.5
C2'—C3—C4	121.8 (8)	H4MA—C4M—H4MB	109.5
C2'—C3—C2	115.5 (9)	H4MA—C4M—H4MC	109.5
C5—C6—H6	121.3	H4MB—C4M—H4MC	109.5
C7—C6—H6	121.3	C9—C10—H10	119.7
C7—C6—C5	117.4 (16)	C11—C10—C9	120.7 (12)
C4—C5—C6	121.1 (14)	C11—C10—H10	119.7
C4—C5—H5	119.5	C13'—C12'—C11'	126.1 (16)
C6—C5—H5	119.5	C13'—C12'—H12'	116.9
N1—C1—C8	120.6 (10)	C11'—C12'—H12'	116.9
C2—C1—N1	120.7 (9)	C9'—C8'—C13'	118.1 (15)
C2—C1—C8	118.7 (12)	C9'—C8'—C1'	122.8 (11)
C16—C15—C14	119.6 (12)	C13'—C8'—C1'	118.9 (15)
O1—C17—C16'—C15'	178.6 (15)	C5—C4—C3—C2	−33.8 (18)
C4—C5'—C6'—C7	1.3 (16)	C5—C4—C3—C2'	149.2 (12)
C4—C3—C2—C1	−176.1 (15)	C5—C6—C7—C6'	1.4 (18)
C4—C3—C2'—C1'	176.4 (15)	C1—N1—C14—C15'	−76.0 (17)
N1—C14—C15—C16	179.1 (14)	C1—N1—C14—C15	106.7 (16)
N1—C1—C2—C3	3 (2)	C1—N1—C1'—C2'	7.3 (18)
N1—C1—C8—C13	132 (2)	C1—N1—C1'—C8'	−175.3 (13)
N1—C1—C8—C9	−55 (2)	C15—C16—C17—O1	−176.8 (15)
N1—C1'—C2'—C3	−3 (2)	C15—C16—C17—C16'	2 (2)
N1—C1'—C8'—C9'	−58.4 (18)	C1'—N1—C14—C15'	105.6 (13)
N1—C1'—C8'—C13'	127.2 (13)	C1'—N1—C14—C15	−72 (2)
C10'—C9'—C8'—C13'	0.2 (18)	C1'—N1—C1—C2	−7.1 (18)
C10'—C9'—C8'—C1'	−174.2 (8)	C1'—N1—C1—C8	175.0 (14)
C10'—C11'—C12'—C13'	1 (2)	C7—C6—C5—C4	−2.0 (15)
C9'—C10'—C11'—C12'	1 (2)	C2—C3—C2'—C1'	−0.9 (18)
C5'—C4—C3—C2	141.7 (14)	C2—C1—C8—C13	−46 (3)
C5'—C4—C3—C2'	−35.4 (16)	C2—C1—C8—C9	127 (2)
C5'—C4—C5—C6	2.2 (15)	C8—C1—C2—C3	−179.1 (15)
C5'—C6'—C7—C6	−1.1 (19)	C8—C13—C12—C11	−1 (3)
C16—C17—C16'—C15'	0 (2)	C8—C9—C10—C11	1 (3)
C17—C16—C15—C14	−3 (2)	C2'—C3—C2—C1	1 (2)
C17—C16'—C15'—C14	−1 (2)	C2'—C1'—C8'—C9'	119.0 (15)
C16'—C15'—C14—N1	−177.4 (14)	C2'—C1'—C8'—C13'	−55.4 (16)
C16'—C15'—C14—C15	0.0 (19)	C12—C13—C8—C1	173.6 (19)
C15'—C14—C15—C16	2 (2)	C12—C13—C8—C9	1 (3)
C11'—C10'—C9'—C8'	−1.0 (19)	C12—C11—C10—C9	−2 (4)
C14—N1—C1—C2	174.4 (14)	C10—C9—C8—C1	−173.4 (18)
C14—N1—C1—C8	−3.5 (18)	C10—C9—C8—C13	−1 (3)
C14—N1—C1'—C2'	−174.2 (14)	C10—C11—C12—C13	2 (4)
C14—N1—C1'—C8'	3 (2)	C12'—C13'—C8'—C9'	0.9 (16)
C3—C4—C5'—C6'	−177.4 (9)	C12'—C13'—C8'—C1'	175.5 (10)
C3—C4—C5—C6	177.9 (8)	C8'—C13'—C12'—C11'	−1 (2)
C5—C4—C5'—C6'	−1.9 (14)	C8'—C1'—C2'—C3	179.2 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1M—H1M···O1^i	0.82	2.02	2.78 (4)	153

Symmetry code: (i) −x+3/2, y−1/2, −z+1/2.

4-(2,4,6-triphenylpyridinium-1-yl)-phenolate tetramethanol solvate (et1_meoh_1_17gpa)

Crystal data

C29H21NO·4(CH4O)	F(000) = 1128
Mr = 527.63	Dx = 1.276 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.425 (3) Å	Cell parameters from 1800 reflections
b = 19.26 (7) Å	θ = 2.4–25.0°
c = 13.112 (4) Å	µ = 0.09 mm^−1
β = 95.70 (3)°	T = 293 K
V = 2620 (9) Å^3	Block, clear orangish yellow
Z = 4	0.33 × 0.13 × 0.05 mm

Data collection

New Xcalibur, EosS2 diffractometer	380 reflections with I > 2σ(I)
ω scans	Rint = 0.163
Absorption correction: analytical CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	θmax = 26.8°, θmin = 2.2°
Tmin = 0.992, Tmax = 0.998	h = −11→12
3529 measured reflections	k = −5→5
1064 independent reflections	l = −16→16

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.080	w = 1/[σ^2(Fo^2) + (0.1342P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.280	(Δ/σ)max < 0.001
S = 1.02	Δρmax = 0.15 e Å^−3
1064 reflections	Δρmin = −0.12 e Å^−3
361 parameters	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
864 restraints

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.4100 (10)	0.3737 (17)	0.1680 (8)	0.065 (9)
C4	1.2221 (17)	0.1504 (15)	0.4108 (12)	0.052 (10)
N1	0.8525 (11)	0.2349 (14)	0.3166 (9)	0.057 (7)
C10'	0.7941 (14)	0.421 (2)	0.5059 (12)	0.055 (10)
H10'	0.776961	0.465918	0.482703	0.066*
C9'	0.834 (2)	0.3729 (17)	0.4386 (17)	0.062 (10)
H9'	0.845110	0.384816	0.371224	0.074*
C5'	1.3150 (12)	0.1923 (18)	0.4603 (9)	0.058 (11)
H5'	1.295584	0.237693	0.477572	0.069*
C6'	1.4365 (16)	0.1665 (17)	0.4838 (12)	0.059 (13)
H6'	1.499495	0.194983	0.516906	0.071*
C13'	0.8443 (14)	0.2884 (19)	0.5734 (11)	0.058 (12)
H13'	0.860923	0.243295	0.596306	0.069*
C16	0.5112 (15)	0.2917 (19)	0.2794 (11)	0.064 (12)
H16	0.434134	0.282745	0.307148	0.077*
C17	0.5157 (17)	0.3402 (19)	0.2026 (12)	0.069 (11)
C16'	0.6329 (13)	0.3535 (18)	0.1664 (10)	0.060 (10)
H16'	0.638113	0.386645	0.115407	0.072*
C15'	0.7409 (15)	0.3189 (15)	0.2039 (11)	0.050 (6)
H15'	0.818540	0.328812	0.177619	0.060*
C2M	0.864 (3)	0.046 (2)	0.440 (2)	0.15 (2)
H2MA	0.823814	0.028152	0.375858	0.227*
H2MB	0.855701	0.012937	0.493083	0.227*
H2MC	0.953186	0.055057	0.433572	0.227*
C11'	0.7781 (18)	0.4053 (19)	0.6066 (14)	0.054 (12)
H11'	0.750120	0.438537	0.650807	0.065*
C14	0.7389 (15)	0.2700 (17)	0.2792 (11)	0.055 (6)
O1M	1.0631 (12)	−0.014 (3)	0.2195 (11)	0.18 (5)
H1M	1.044648	−0.032706	0.272056	0.200*
C3	1.0869 (14)	0.1770 (15)	0.3817 (11)	0.048 (6)
C6	1.3711 (14)	0.0576 (19)	0.4157 (11)	0.068 (11)
H6	1.389099	0.011411	0.402287	0.081*
C5	1.2484 (18)	0.0820 (15)	0.3908 (14)	0.071 (10)
H5	1.184098	0.052827	0.360980	0.085*
C1	0.9036 (14)	0.1865 (16)	0.2583 (11)	0.057 (6)
C15	0.6218 (12)	0.257 (2)	0.3147 (11)	0.056 (11)
H15	0.617061	0.222658	0.364466	0.067*
O4M	0.995 (2)	0.458 (3)	0.2889 (15)	0.16 (4)
H4M	1.066716	0.458496	0.268945	0.243*
O3M	1.1697 (19)	0.388 (2)	0.206 (2)	0.14 (4)
H3M	1.246492	0.388386	0.197409	0.206*
C13	0.9026 (19)	0.151 (3)	0.0759 (11)	0.078 (12)
H13	0.988172	0.165281	0.078918	0.093*
C1'	0.9161 (15)	0.253 (2)	0.4080 (13)	0.058 (9)
C9	0.7082 (16)	0.138 (2)	0.1538 (15)	0.078 (13)
H9	0.661428	0.143573	0.210024	0.093*
C7	1.4684 (18)	0.0993 (17)	0.4599 (13)	0.063 (14)
H7	1.552315	0.082873	0.473114	0.076*
C2	1.0202 (12)	0.158 (2)	0.2917 (9)	0.056 (9)
H2	1.055447	0.125073	0.251256	0.067*
C8	0.8346 (13)	0.158 (2)	0.1601 (10)	0.055 (10)
C2'	1.0319 (14)	0.2245 (16)	0.4396 (11)	0.061 (9)
H2'	1.074336	0.237612	0.502403	0.073*
C11	0.7192 (18)	0.102 (2)	−0.0162 (15)	0.103 (8)
H11	0.679968	0.081229	−0.075617	0.123*
C1M	0.954 (2)	−0.008 (3)	0.1506 (18)	0.15 (5)
H1MA	0.977614	0.006576	0.085309	0.218*
H1MB	0.895405	0.024635	0.175566	0.218*
H1MC	0.912298	−0.052924	0.143260	0.218*
C12	0.8430 (17)	0.122 (2)	−0.0130 (14)	0.089 (7)
H12	0.888008	0.117359	−0.070331	0.107*
C3M	1.134 (2)	0.322 (2)	0.226 (2)	0.08 (4)
H3MA	1.180766	0.290030	0.187498	0.119*
H3MB	1.043427	0.316551	0.207809	0.119*
H3MC	1.153536	0.312582	0.298184	0.119*
O2M	0.8045 (15)	0.106 (2)	0.4623 (12)	0.086 (11)
H2M	0.825090	0.116267	0.522469	0.129*
C4M	0.9141 (19)	0.494 (3)	0.2243 (16)	0.15 (4)
H4MA	0.877461	0.463240	0.171021	0.221*
H4MB	0.959803	0.530472	0.194674	0.221*
H4MC	0.846486	0.512642	0.260367	0.221*
C10	0.6508 (19)	0.110 (2)	0.0655 (13)	0.094 (13)
H10	0.564732	0.096643	0.061340	0.113*
C12'	0.805 (2)	0.3385 (17)	0.6389 (19)	0.075 (14)
H12'	0.796690	0.326794	0.706707	0.090*
C8'	0.8582 (16)	0.3065 (17)	0.4740 (12)	0.045 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.055 (6)	0.06 (2)	0.081 (7)	−0.001 (11)	−0.001 (6)	−0.012 (12)
C4	0.048 (7)	0.07 (3)	0.045 (10)	0.016 (11)	0.012 (6)	−0.004 (15)
N1	0.043 (6)	0.070 (18)	0.057 (7)	0.010 (10)	−0.001 (5)	−0.008 (9)
C10'	0.057 (10)	0.04 (3)	0.065 (10)	0.003 (18)	−0.007 (9)	0.000 (16)
C9'	0.087 (14)	0.04 (3)	0.052 (11)	0.006 (17)	−0.013 (11)	−0.003 (14)
C5'	0.052 (8)	0.07 (3)	0.049 (10)	0.023 (13)	0.006 (8)	−0.018 (16)
C6'	0.051 (9)	0.08 (4)	0.043 (10)	0.019 (14)	0.004 (8)	0.010 (16)
C13'	0.091 (12)	0.04 (4)	0.044 (8)	0.02 (2)	0.002 (9)	−0.003 (14)
C16	0.052 (8)	0.09 (3)	0.055 (10)	0.021 (14)	0.013 (9)	−0.010 (16)
C17	0.063 (8)	0.09 (3)	0.053 (10)	0.015 (13)	−0.002 (8)	−0.011 (16)
C16'	0.060 (8)	0.08 (3)	0.042 (9)	0.013 (13)	−0.009 (7)	−0.005 (15)
C15'	0.046 (7)	0.050 (13)	0.052 (8)	−0.004 (8)	0.001 (6)	−0.006 (9)
C2M	0.19 (3)	0.09 (5)	0.18 (3)	−0.01 (4)	0.08 (2)	0.00 (5)
C11'	0.064 (11)	0.03 (4)	0.066 (11)	0.005 (19)	0.015 (10)	−0.006 (17)
C14	0.047 (6)	0.057 (12)	0.060 (8)	0.001 (8)	0.000 (6)	0.002 (9)
O1M	0.105 (11)	0.30 (15)	0.143 (13)	−0.04 (2)	−0.024 (8)	0.00 (3)
C3	0.055 (6)	0.046 (14)	0.041 (7)	0.010 (8)	0.003 (5)	−0.004 (9)
C6	0.059 (9)	0.08 (3)	0.064 (11)	0.035 (14)	0.007 (9)	−0.003 (17)
C5	0.068 (9)	0.07 (3)	0.070 (13)	0.029 (13)	−0.017 (10)	−0.011 (16)
C1	0.059 (7)	0.056 (13)	0.055 (7)	0.003 (8)	−0.004 (6)	−0.004 (8)
C15	0.048 (7)	0.07 (3)	0.052 (9)	0.004 (12)	0.006 (7)	−0.006 (15)
O4M	0.18 (2)	0.17 (12)	0.134 (14)	−0.01 (3)	0.023 (11)	0.06 (3)
O3M	0.088 (15)	0.15 (12)	0.177 (19)	−0.04 (3)	0.037 (13)	0.08 (3)
C13	0.128 (12)	0.06 (4)	0.044 (8)	0.023 (17)	−0.004 (8)	0.017 (14)
C1'	0.055 (9)	0.06 (3)	0.057 (8)	0.021 (12)	−0.002 (6)	−0.004 (11)
C9	0.073 (9)	0.06 (4)	0.094 (11)	0.012 (16)	−0.034 (8)	0.006 (17)
C7	0.035 (9)	0.09 (4)	0.071 (13)	0.028 (13)	0.022 (8)	0.013 (17)
C2	0.057 (8)	0.07 (3)	0.036 (7)	0.016 (12)	0.003 (6)	−0.016 (13)
C8	0.066 (8)	0.05 (3)	0.043 (7)	0.021 (14)	−0.024 (6)	0.013 (12)
C2'	0.068 (10)	0.07 (2)	0.038 (8)	0.034 (14)	−0.011 (7)	−0.014 (12)
C11	0.118 (10)	0.098 (15)	0.087 (9)	0.002 (10)	−0.019 (8)	0.010 (11)
C1M	0.093 (14)	0.25 (15)	0.089 (14)	0.03 (3)	−0.007 (9)	−0.07 (3)
C12	0.112 (9)	0.088 (15)	0.069 (8)	0.004 (10)	0.009 (7)	−0.008 (10)
C3M	0.051 (14)	0.09 (11)	0.094 (18)	−0.04 (3)	0.006 (13)	−0.05 (4)
O2M	0.084 (9)	0.08 (3)	0.086 (10)	−0.005 (16)	−0.013 (8)	0.043 (16)
C4M	0.080 (15)	0.23 (12)	0.125 (19)	−0.07 (3)	−0.025 (12)	0.05 (4)
C10	0.081 (11)	0.09 (4)	0.108 (12)	−0.015 (17)	−0.020 (8)	−0.008 (18)
C12'	0.130 (18)	0.04 (4)	0.055 (12)	0.02 (2)	0.019 (12)	−0.003 (15)
C8'	0.043 (9)	0.05 (3)	0.040 (8)	0.014 (14)	−0.009 (8)	0.002 (12)

Geometric parameters (Å, º)

O1—C17	1.32 (3)	C6—H6	0.9300
C4—C5'	1.374 (17)	C6—C5	1.371 (15)
C4—C3	1.51 (2)	C6—C7	1.376 (17)
C4—C5	1.377 (18)	C5—H5	0.9300
N1—C14	1.41 (2)	C1—C2	1.364 (17)
N1—C1	1.35 (2)	C1—C8	1.51 (2)
N1—C1'	1.357 (19)	C15—H15	0.9300
C10'—H10'	0.9300	O4M—H4M	0.8206
C10'—C9'	1.374 (18)	O4M—C4M	1.32 (3)
C10'—C11'	1.381 (15)	O3M—H3M	0.8200
C9'—H9'	0.9300	O3M—C3M	1.35 (3)
C9'—C8'	1.374 (19)	C13—H13	0.9300
C5'—H5'	0.9300	C13—C8	1.377 (14)
C5'—C6'	1.367 (16)	C13—C12	1.381 (16)
C6'—H6'	0.9300	C1'—C2'	1.356 (17)
C6'—C7	1.380 (18)	C1'—C8'	1.51 (3)
C13'—H13'	0.9300	C9—H9	0.9300
C13'—C12'	1.381 (18)	C9—C8	1.368 (15)
C13'—C8'	1.371 (15)	C9—C10	1.361 (16)
C16—H16	0.9300	C7—H7	0.9300
C16—C17	1.378 (17)	C2—H2	0.9300
C16—C15	1.376 (16)	C2'—H2'	0.9300
C17—C16'	1.378 (15)	C11—H11	0.9300
C16'—H16'	0.9300	C11—C12	1.348 (16)
C16'—C15'	1.358 (16)	C11—C10	1.354 (15)
C15'—H15'	0.9300	C1M—H1MA	0.9600
C15'—C14	1.367 (17)	C1M—H1MB	0.9600
C2M—H2MA	0.9600	C1M—H1MC	0.9600
C2M—H2MB	0.9600	C12—H12	0.9300
C2M—H2MC	0.9600	C3M—H3MA	0.9600
C2M—O2M	1.36 (3)	C3M—H3MB	0.9600
C11'—H11'	0.9300	C3M—H3MC	0.9600
C11'—C12'	1.374 (19)	O2M—H2M	0.8200
C14—C15	1.373 (14)	C4M—H4MA	0.9603
O1M—H1M	0.8200	C4M—H4MB	0.9604
O1M—C1M	1.387 (17)	C4M—H4MC	0.9604
C3—C2	1.357 (15)	C10—H10	0.9300
C3—C2'	1.353 (18)	C12'—H12'	0.9300
C5'—C4—C3	121.1 (16)	C14—C15—C16	123 (2)
C5'—C4—C5	121 (2)	C14—C15—H15	118.7
C5—C4—C3	118.3 (16)	C4M—O4M—H4M	109.4
C1—N1—C14	120.0 (12)	C3M—O3M—H3M	109.5
C1—N1—C1'	119.7 (18)	C8—C13—H13	120.3
C1'—N1—C14	120.1 (16)	C8—C13—C12	120 (2)
C9'—C10'—H10'	118.6	C12—C13—H13	120.2
C9'—C10'—C11'	123 (3)	N1—C1'—C8'	119.8 (15)
C11'—C10'—H10'	118.6	C2'—C1'—N1	120 (2)
C10'—C9'—H9'	121.1	C2'—C1'—C8'	119.9 (18)
C10'—C9'—C8'	118 (3)	C8—C9—H9	119.9
C8'—C9'—H9'	121.1	C10—C9—H9	119.9
C4—C5'—H5'	120.5	C10—C9—C8	120 (2)
C6'—C5'—C4	119 (2)	C6'—C7—H7	121.4
C6'—C5'—H5'	120.5	C6—C7—C6'	117 (2)
C5'—C6'—H6'	119.0	C6—C7—H7	121.4
C5'—C6'—C7	122 (3)	C3—C2—C1	122 (2)
C7—C6'—H6'	119.0	C3—C2—H2	118.7
C12'—C13'—H13'	120.7	C1—C2—H2	118.8
C8'—C13'—H13'	120.7	C13—C8—C1	118.7 (15)
C8'—C13'—C12'	119 (3)	C9—C8—C1	121.8 (15)
C17—C16—H16	120.3	C9—C8—C13	119.5 (18)
C15—C16—H16	120.3	C3—C2'—C1'	121.3 (19)
C15—C16—C17	119.3 (19)	C3—C2'—H2'	119.4
O1—C17—C16	119.7 (17)	C1'—C2'—H2'	119.4
O1—C17—C16'	122 (2)	C12—C11—H11	119.4
C16—C17—C16'	118 (2)	C12—C11—C10	121 (2)
C17—C16'—H16'	119.4	C10—C11—H11	119.4
C15'—C16'—C17	121 (2)	O1M—C1M—H1MA	109.4
C15'—C16'—H16'	119.5	O1M—C1M—H1MB	109.4
C16'—C15'—H15'	119.1	O1M—C1M—H1MC	109.6
C16'—C15'—C14	121.9 (18)	H1MA—C1M—H1MB	109.5
C14—C15'—H15'	119.1	H1MA—C1M—H1MC	109.5
H2MA—C2M—H2MB	109.5	H1MB—C1M—H1MC	109.5
H2MA—C2M—H2MC	109.5	C13—C12—H12	120.2
H2MB—C2M—H2MC	109.5	C11—C12—C13	120 (2)
O2M—C2M—H2MA	109.4	C11—C12—H12	120.2
O2M—C2M—H2MB	109.5	O3M—C3M—H3MA	109.4
O2M—C2M—H2MC	109.5	O3M—C3M—H3MB	109.5
C10'—C11'—H11'	121.4	O3M—C3M—H3MC	109.5
C12'—C11'—C10'	117 (3)	H3MA—C3M—H3MB	109.5
C12'—C11'—H11'	121.4	H3MA—C3M—H3MC	109.5
C15'—C14—N1	120.6 (12)	H3MB—C3M—H3MC	109.5
C15'—C14—C15	116.8 (19)	C2M—O2M—H2M	109.4
C15—C14—N1	122.5 (17)	O4M—C4M—H4MA	109.4
C1M—O1M—H1M	109.4	O4M—C4M—H4MB	109.7
C2—C3—C4	120.9 (14)	O4M—C4M—H4MC	109.5
C2'—C3—C4	121.6 (12)	H4MA—C4M—H4MB	109.4
C2'—C3—C2	117.3 (19)	H4MA—C4M—H4MC	109.4
C5—C6—H6	118.9	H4MB—C4M—H4MC	109.4
C5—C6—C7	122 (3)	C9—C10—H10	120.0
C7—C6—H6	118.9	C11—C10—C9	120 (2)
C4—C5—H5	120.6	C11—C10—H10	120.1
C6—C5—C4	119 (3)	C13'—C12'—H12'	119.1
C6—C5—H5	120.6	C11'—C12'—C13'	122 (3)
N1—C1—C2	118.9 (17)	C11'—C12'—H12'	119.1
N1—C1—C8	123.4 (16)	C9'—C8'—C1'	121 (2)
C2—C1—C8	117.7 (18)	C13'—C8'—C9'	122 (3)
C16—C15—H15	118.7	C13'—C8'—C1'	117 (2)
O1—C17—C16'—C15'	179 (3)	C5—C4—C3—C2	−41 (3)
C4—C5'—C6'—C7	−0.4 (18)	C5—C4—C3—C2'	144 (2)
C4—C3—C2—C1	−173.4 (19)	C5—C6—C7—C6'	3 (3)
C4—C3—C2'—C1'	173 (2)	C1—N1—C14—C15'	−73 (2)
N1—C14—C15—C16	178.9 (19)	C1—N1—C14—C15	106.6 (19)
N1—C1—C2—C3	0 (2)	C1—N1—C1'—C2'	2 (3)
N1—C1—C8—C13	136 (3)	C1—N1—C1'—C8'	−179 (2)
N1—C1—C8—C9	−46 (4)	C15—C16—C17—O1	180 (2)
N1—C1'—C2'—C3	0 (4)	C15—C16—C17—C16'	−2 (2)
N1—C1'—C8'—C9'	−61 (3)	C1'—N1—C14—C15'	103 (2)
N1—C1'—C8'—C13'	126 (2)	C1'—N1—C14—C15	−78 (2)
C10'—C9'—C8'—C13'	−1 (3)	C1'—N1—C1—C2	−1.6 (19)
C10'—C9'—C8'—C1'	−173.4 (16)	C1'—N1—C1—C8	175 (3)
C10'—C11'—C12'—C13'	−1 (3)	C7—C6—C5—C4	0 (3)
C9'—C10'—C11'—C12'	0 (3)	C2—C3—C2'—C1'	−1 (3)
C5'—C4—C3—C2	142 (2)	C2—C1—C8—C13	−48 (3)
C5'—C4—C3—C2'	−33 (3)	C2—C1—C8—C9	130 (3)
C5'—C4—C5—C6	−4 (3)	C8—C1—C2—C3	−176 (3)
C5'—C6'—C7—C6	−3 (2)	C8—C13—C12—C11	0 (2)
C16—C17—C16'—C15'	1.1 (19)	C8—C9—C10—C11	0 (3)
C17—C16—C15—C14	3 (3)	C2'—C3—C2—C1	1 (3)
C17—C16'—C15'—C14	0 (2)	C2'—C1'—C8'—C9'	119 (3)
C16'—C15'—C14—N1	179.9 (18)	C2'—C1'—C8'—C13'	−54 (3)
C16'—C15'—C14—C15	1 (3)	C12—C13—C8—C1	177 (3)
C15'—C14—C15—C16	−2 (3)	C12—C13—C8—C9	−1 (3)
C11'—C10'—C9'—C8'	1 (3)	C12—C11—C10—C9	−2 (4)
C14—N1—C1—C2	173.5 (18)	C10—C9—C8—C1	−177 (3)
C14—N1—C1—C8	−10 (3)	C10—C9—C8—C13	1 (3)
C14—N1—C1'—C2'	−174 (2)	C10—C11—C12—C13	2 (3)
C14—N1—C1'—C8'	6 (3)	C12'—C13'—C8'—C9'	0 (2)
C3—C4—C5'—C6'	−179.0 (13)	C12'—C13'—C8'—C1'	172.9 (18)
C3—C4—C5—C6	179.2 (13)	C8'—C13'—C12'—C11'	1 (2)
C5—C4—C5'—C6'	4 (2)	C8'—C1'—C2'—C3	−179 (2)

4-(2,4,6-triphenylpyridinium-1-yl)-phenolate ethanol solvate (et1_ethanol_0_24gpa)

Crystal data

C29H21NO·4(C2H6O)·O	Dx = 1.144 Mg m^−3
Mr = 599.74	Mo Kα radiation, λ = 0.71073 Å
Trigonal, R3c	Cell parameters from 979 reflections
a = 24.062 (9) Å	θ = 2.0–26.4°
c = 31.259 (8) Å	µ = 0.08 mm^−1
V = 15673 (12) Å^3	T = 293 K
Z = 18	Block, clear red
F(000) = 5796	0.56 × 0.11 × 0.1 mm

Data collection

New Xcalibur, EosS2 diffractometer	825 reflections with I > 2σ(I)
Detector resolution: 8.0169 pixels mm^-1	Rint = 0.201
ω scans	θmax = 26.4°, θmin = 4.6°
Absorption correction: analytical CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −27→27
Tmin = 0.958, Tmax = 0.972	k = −7→7
9812 measured reflections	l = −37→37
3310 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.121	w = 1/[σ^2(Fo^2) + (0.2P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.459	Δρmax = 0.29 e Å^−3
S = 0.97	Δρmin = −0.27 e Å^−3
3310 reflections	Absolute structure: Flack x determined using 189 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
360 parameters	Absolute structure parameter: −5.7 (10)
386 restraints

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C3	−0.001 (3)	0.3660 (17)	0.1246 (16)	0.079 (8)
C2	0.031 (2)	0.4121 (15)	0.0938 (16)	0.078 (11)
H2	0.055213	0.405321	0.073310	0.094*
C1	0.0285 (18)	0.4677 (14)	0.0925 (13)	0.085 (12)
N1	0.0020 (18)	0.4813 (13)	0.1266 (13)	0.077 (7)
C1'	−0.0292 (16)	0.4370 (14)	0.1579 (13)	0.071 (11)
C2'	−0.025 (2)	0.3830 (16)	0.1593 (15)	0.069 (10)
H2'	−0.037363	0.357479	0.183748	0.083*
C13'	−0.0536 (13)	0.4358 (14)	0.2343 (13)	0.077 (11)
H13'	−0.022874	0.424127	0.240054	0.093*
C8'	−0.0636 (13)	0.4487 (12)	0.1926 (12)	0.076 (11)
C9'	−0.1095 (14)	0.4661 (13)	0.1840 (12)	0.085 (11)
H9'	−0.116221	0.474713	0.156100	0.101*
C10'	−0.1454 (12)	0.4708 (13)	0.2173 (14)	0.096 (12)
H10'	−0.176093	0.482456	0.211546	0.116*
C11'	−0.1354 (14)	0.4579 (14)	0.2590 (13)	0.104 (13)
H11'	−0.159356	0.461034	0.281246	0.125*
C12'	−0.0895 (16)	0.4405 (16)	0.2676 (12)	0.111 (13)
H12'	−0.082748	0.431869	0.295501	0.133*
O1	−0.0039 (18)	0.7089 (12)	0.1263 (14)	0.116 (8)
C15'	−0.0300 (11)	0.5538 (9)	0.0934 (12)	0.080 (11)
H15'	−0.049953	0.524158	0.071574	0.096*
C16'	−0.0313 (12)	0.6109 (10)	0.0935 (12)	0.092 (12)
H16'	−0.052203	0.619433	0.071620	0.111*
C17	−0.0014 (14)	0.6552 (9)	0.1262 (13)	0.094 (9)
C16	0.0298 (12)	0.6425 (10)	0.1588 (12)	0.090 (12)
H16	0.049816	0.672142	0.180700	0.108*
C15	0.0312 (12)	0.5854 (11)	0.1588 (12)	0.079 (11)
H15	0.052067	0.576868	0.180655	0.095*
C14	0.0013 (13)	0.5411 (9)	0.1261 (13)	0.060 (6)
C8	0.0644 (12)	0.5153 (12)	0.0591 (12)	0.061 (10)
C13	0.0531 (12)	0.4909 (10)	0.0177 (13)	0.098 (14)
H13	0.022341	0.448315	0.012721	0.118*
C12	0.0879 (14)	0.5303 (14)	−0.0163 (12)	0.082 (12)
H12	0.080322	0.513997	−0.043995	0.098*
C11	0.1339 (13)	0.5940 (12)	−0.0089 (13)	0.092 (12)
H11	0.157109	0.620333	−0.031629	0.111*
C10	0.1451 (11)	0.6184 (10)	0.0325 (14)	0.085 (12)
H10	0.175915	0.660991	0.037454	0.102*
C9	0.1104 (13)	0.5790 (13)	0.0665 (12)	0.082 (13)
H9	0.117935	0.595309	0.094172	0.099*
C5	0.0517 (16)	0.3043 (10)	0.1056 (12)	0.086 (11)
H5	0.082506	0.341002	0.091634	0.104*
C4	0.001 (2)	0.3045 (11)	0.1264 (13)	0.084 (8)
C5'	−0.0453 (15)	0.2496 (16)	0.1472 (11)	0.091 (11)
H5'	−0.079332	0.249794	0.161086	0.109*
C6'	−0.0404 (15)	0.1945 (11)	0.1472 (11)	0.100 (11)
H6'	−0.071159	0.157721	0.161108	0.120*
C7	0.0106 (19)	0.1942 (11)	0.1264 (13)	0.099 (10)
H7	0.013846	0.157288	0.126393	0.119*
C6	0.0566 (15)	0.2491 (15)	0.1056 (12)	0.100 (11)
H6	0.090679	0.248928	0.091656	0.120*
O1E	−0.1271 (18)	0.4095 (18)	0.0728 (16)	0.22 (2)
H1E	−0.111063	0.402362	0.051885	0.330*
C1E	−0.214 (2)	0.429 (3)	0.077 (2)	0.20 (3)
H1EA	−0.181111	0.472554	0.072983	0.296*
H1EB	−0.226028	0.421976	0.106896	0.296*
H1EC	−0.250594	0.419301	0.060074	0.296*
C3E	−0.144 (2)	0.269 (2)	0.041 (2)	0.21 (3)
H3EA	−0.148733	0.267975	0.071662	0.247*
H3EB	−0.122884	0.243900	0.034517	0.247*
C2E	−0.1901 (19)	0.388 (2)	0.065 (2)	0.18 (2)
H2EA	−0.214912	0.347391	0.080326	0.222*
H2EB	−0.197964	0.378916	0.034983	0.222*
O2E	−0.1020 (17)	0.3310 (14)	0.02923 (2)	0.163 (15)
H2E	−0.089 (4)	0.324 (3)	0.0041 (14)	0.244*
C4E	−0.204 (2)	0.237 (2)	0.023 (2)	0.19 (2)
H4EA	−0.206230	0.262262	0.000348	0.291*
H4EB	−0.234889	0.230404	0.044711	0.291*
H4EC	−0.211865	0.196360	0.012309	0.291*
C6E	0.194 (2)	0.588 (2)	0.187 (2)	0.19 (3)
H6EA	0.228124	0.581490	0.176361	0.231*
H6EB	0.196019	0.587734	0.218075	0.231*
O3E	0.1376 (19)	0.5379 (17)	0.1748 (14)	0.167 (16)
H3E	0.135675	0.504472	0.182737	0.251*
C5E	0.208 (3)	0.650 (2)	0.175 (2)	0.23 (3)
H5EA	0.253467	0.678849	0.177233	0.343*
H5EB	0.185372	0.663897	0.192678	0.343*
H5EC	0.195290	0.648708	0.145445	0.343*
C8E	0.121 (2)	0.406 (2)	0.2085 (18)	0.15 (2)
H8EA	0.124340	0.414846	0.177988	0.183*
H8EB	0.088464	0.361710	0.212482	0.183*
C7E	0.180 (2)	0.413 (2)	0.2218 (19)	0.16 (2)
H7EA	0.179552	0.408146	0.252291	0.240*
H7EB	0.214239	0.454354	0.213732	0.240*
H7EC	0.185963	0.380234	0.208437	0.240*
O4E	0.1015 (18)	0.444 (2)	0.2279 (11)	0.21 (2)
H4E	0.087 (10)	0.436 (4)	0.255 (3)	0.319*
O2W	0.333333	0.666667	0.062 (2)	0.22 (3)*
O3W	0.333333	0.666667	0.288 (6)	0.39 (5)*
O1W	−0.302 (4)	0.363 (5)	0.175 (3)	0.16 (5)*	0.3333

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C3	0.09 (2)	0.08 (3)	0.085 (16)	0.05 (2)	−0.003 (13)	−0.015 (19)
C2	0.10 (3)	0.06 (3)	0.075 (19)	0.04 (2)	−0.006 (16)	−0.026 (18)
C1	0.11 (3)	0.08 (2)	0.08 (2)	0.06 (2)	−0.001 (19)	−0.01 (2)
N1	0.095 (19)	0.08 (2)	0.075 (13)	0.05 (2)	−0.012 (12)	−0.016 (19)
C1'	0.09 (3)	0.06 (3)	0.07 (2)	0.04 (2)	−0.01 (2)	−0.02 (2)
C2'	0.07 (3)	0.07 (3)	0.071 (18)	0.04 (2)	−0.013 (16)	−0.003 (19)
C13'	0.10 (3)	0.07 (2)	0.060 (16)	0.04 (2)	0.007 (17)	−0.032 (19)
C8'	0.10 (3)	0.04 (2)	0.076 (16)	0.026 (19)	0.004 (19)	0.002 (19)
C9'	0.08 (3)	0.08 (3)	0.073 (18)	0.03 (2)	−0.001 (17)	−0.024 (19)
C10'	0.10 (3)	0.08 (3)	0.09 (2)	0.02 (2)	0.01 (2)	−0.04 (2)
C11'	0.10 (3)	0.12 (3)	0.084 (17)	0.05 (2)	0.02 (2)	−0.03 (2)
C12'	0.10 (3)	0.15 (3)	0.084 (19)	0.06 (2)	0.028 (19)	−0.03 (2)
O1	0.20 (3)	0.12 (3)	0.091 (12)	0.14 (3)	−0.019 (13)	−0.02 (2)
C15'	0.09 (3)	0.08 (2)	0.08 (2)	0.04 (2)	−0.008 (16)	0.01 (2)
C16'	0.10 (3)	0.08 (3)	0.10 (2)	0.05 (2)	−0.026 (19)	0.01 (2)
C17	0.12 (3)	0.08 (3)	0.079 (16)	0.04 (3)	0.011 (14)	0.02 (2)
C16	0.10 (3)	0.07 (2)	0.070 (19)	0.02 (2)	0.001 (16)	0.01 (2)
C15	0.07 (2)	0.08 (3)	0.069 (19)	0.02 (2)	0.000 (16)	0.01 (2)
C14	0.053 (18)	0.08 (2)	0.061 (13)	0.05 (2)	0.015 (11)	0.01 (2)
C8	0.061 (15)	0.060 (14)	0.066 (13)	0.034 (10)	0.005 (11)	−0.006 (11)
C13	0.09 (3)	0.09 (3)	0.083 (19)	0.02 (2)	0.01 (2)	−0.021 (16)
C12	0.08 (3)	0.12 (3)	0.064 (16)	0.06 (2)	0.003 (17)	−0.001 (19)
C11	0.09 (3)	0.10 (3)	0.096 (19)	0.06 (2)	0.04 (2)	0.014 (19)
C10	0.07 (2)	0.07 (2)	0.13 (2)	0.035 (18)	0.04 (2)	−0.011 (16)
C9	0.07 (2)	0.07 (2)	0.09 (2)	0.025 (18)	0.035 (18)	−0.034 (16)
C5	0.13 (2)	0.08 (2)	0.06 (2)	0.06 (2)	0.002 (17)	0.00 (2)
C4	0.15 (2)	0.07 (2)	0.033 (12)	0.05 (2)	0.018 (13)	0.00 (2)
C5'	0.15 (3)	0.09 (3)	0.05 (2)	0.07 (2)	0.018 (17)	0.01 (2)
C6'	0.16 (3)	0.08 (2)	0.07 (2)	0.07 (2)	0.020 (18)	0.00 (2)
C7	0.18 (3)	0.08 (2)	0.058 (15)	0.08 (2)	0.021 (17)	−0.003 (19)
C6	0.14 (3)	0.11 (3)	0.08 (2)	0.08 (2)	0.007 (18)	0.02 (2)
O1E	0.10 (2)	0.14 (3)	0.40 (6)	0.04 (3)	−0.01 (3)	−0.09 (3)
C1E	0.13 (4)	0.13 (5)	0.33 (7)	0.07 (4)	0.02 (4)	−0.07 (5)
C3E	0.11 (4)	0.12 (3)	0.29 (6)	−0.01 (4)	−0.03 (4)	−0.02 (4)
C2E	0.07 (2)	0.07 (4)	0.37 (6)	0.00 (3)	0.04 (3)	−0.06 (4)
O2E	0.16 (4)	0.12 (3)	0.16 (3)	0.03 (3)	0.00 (3)	−0.01 (3)
C4E	0.15 (4)	0.16 (4)	0.26 (5)	0.07 (3)	−0.09 (4)	−0.10 (4)
C6E	0.17 (4)	0.19 (4)	0.22 (5)	0.09 (3)	−0.07 (4)	−0.07 (4)
O3E	0.15 (3)	0.17 (3)	0.19 (2)	0.083 (19)	−0.057 (19)	−0.02 (2)
C5E	0.27 (6)	0.18 (3)	0.15 (4)	0.05 (4)	−0.13 (4)	−0.06 (4)
C8E	0.15 (2)	0.15 (2)	0.14 (2)	0.063 (16)	−0.014 (13)	0.005 (13)
C7E	0.15 (3)	0.16 (3)	0.18 (3)	0.08 (2)	0.00 (2)	0.00 (2)
O4E	0.25 (5)	0.25 (4)	0.22 (3)	0.18 (4)	0.16 (4)	0.16 (3)

Geometric parameters (Å, º)

C3—C2	1.38 (2)	C5—H5	0.9300
C3—C2'	1.38 (2)	C5—C4	1.3900
C3—C4	1.50 (2)	C5—C6	1.3900
C2—H2	0.9300	C4—C5'	1.3900
C2—C1	1.37 (2)	C5'—H5'	0.9300
C1—N1	1.37 (2)	C5'—C6'	1.3900
C1—C8	1.47 (2)	C6'—H6'	0.9300
N1—C1'	1.36 (2)	C6'—C7	1.3900
N1—C14	1.45 (2)	C7—H7	0.9300
C1'—C2'	1.36 (2)	C7—C6	1.3900
C1'—C8'	1.47 (2)	C6—H6	0.9300
C2'—H2'	0.9300	O1E—H1E	0.8200
C13'—H13'	0.9300	O1E—C2E	1.36 (3)
C13'—C8'	1.3900	C1E—H1EA	0.9600
C13'—C12'	1.3900	C1E—H1EB	0.9600
C8'—C9'	1.3900	C1E—H1EC	0.9600
C9'—H9'	0.9300	C1E—C2E	1.41 (3)
C9'—C10'	1.3900	C3E—H3EA	0.9700
C10'—H10'	0.9300	C3E—H3EB	0.9700
C10'—C11'	1.3900	C3E—O2E	1.37 (3)
C11'—H11'	0.9300	C3E—C4E	1.37 (3)
C11'—C12'	1.3900	C2E—H2EA	0.9700
C12'—H12'	0.9300	C2E—H2EB	0.9700
O1—C17	1.322 (19)	O2E—H2E	0.8900 (16)
C15'—H15'	0.9300	C4E—H4EA	0.9606
C15'—C16'	1.3900	C4E—H4EB	0.9605
C15'—C14	1.3900	C4E—H4EC	0.9606
C16'—H16'	0.9300	C6E—H6EA	0.9700
C16'—C17	1.3900	C6E—H6EB	0.9700
C17—C16	1.3900	C6E—O3E	1.35 (3)
C16—H16	0.9300	C6E—C5E	1.40 (3)
C16—C15	1.3900	O3E—H3E	0.8200
C15—H15	0.9300	C5E—H5EA	0.9609
C15—C14	1.3900	C5E—H5EB	0.9608
C8—C13	1.3900	C5E—H5EC	0.9609
C8—C9	1.3900	C8E—H8EA	0.9700
C13—H13	0.9300	C8E—H8EB	0.9700
C13—C12	1.3900	C8E—C7E	1.40 (3)
C12—H12	0.9300	C8E—O4E	1.36 (3)
C12—C11	1.3900	C7E—H7EA	0.9674
C11—H11	0.9300	C7E—H7EB	0.9666
C11—C10	1.3900	C7E—H7EC	0.9668
C10—H10	0.9300	O4E—H4E	0.890 (4)
C10—C9	1.3900	O1W—O1W^i	1.27 (14)
C9—H9	0.9300	O1W—O1W^ii	1.27 (14)
C2—C3—C2'	117 (2)	C4—C5—H5	120.0
C2—C3—C4	123 (3)	C4—C5—C6	120.0
C2'—C3—C4	119 (3)	C6—C5—H5	120.0
C3—C2—H2	119.2	C5—C4—C3	116 (3)
C1—C2—C3	122 (3)	C5—C4—C5'	120.0
C1—C2—H2	118.9	C5'—C4—C3	124 (3)
C2—C1—C8	119 (3)	C4—C5'—H5'	120.0
N1—C1—C2	118 (3)	C6'—C5'—C4	120.0
N1—C1—C8	122 (2)	C6'—C5'—H5'	120.0
C1—N1—C14	118.0 (17)	C5'—C6'—H6'	120.0
C1'—N1—C1	121 (2)	C5'—C6'—C7	120.0
C1'—N1—C14	120.7 (18)	C7—C6'—H6'	120.0
N1—C1'—C8'	121 (2)	C6'—C7—H7	120.0
C2'—C1'—N1	120 (3)	C6—C7—C6'	120.0
C2'—C1'—C8'	119 (3)	C6—C7—H7	120.0
C3—C2'—H2'	119.8	C5—C6—H6	120.0
C1'—C2'—C3	120 (3)	C7—C6—C5	120.0
C1'—C2'—H2'	120.1	C7—C6—H6	120.0
C8'—C13'—H13'	120.1	C2E—O1E—H1E	109.6
C8'—C13'—C12'	120.0	H1EA—C1E—H1EB	109.4
C12'—C13'—H13'	119.8	H1EA—C1E—H1EC	109.5
C13'—C8'—C1'	118 (2)	H1EB—C1E—H1EC	109.5
C13'—C8'—C9'	120.0	C2E—C1E—H1EA	110.3
C9'—C8'—C1'	122 (2)	C2E—C1E—H1EB	108.7
C8'—C9'—H9'	120.0	C2E—C1E—H1EC	109.4
C8'—C9'—C10'	120.0	H3EA—C3E—H3EB	107.0
C10'—C9'—H9'	120.0	O2E—C3E—H3EA	107.6
C9'—C10'—H10'	120.0	O2E—C3E—H3EB	106.3
C11'—C10'—C9'	120.0	O2E—C3E—C4E	119 (3)
C11'—C10'—H10'	120.0	C4E—C3E—H3EA	108.3
C10'—C11'—H11'	120.0	C4E—C3E—H3EB	107.5
C12'—C11'—C10'	120.0	O1E—C2E—C1E	117 (3)
C12'—C11'—H11'	120.0	O1E—C2E—H2EA	107.5
C13'—C12'—H12'	120.0	O1E—C2E—H2EB	108.1
C11'—C12'—C13'	120.0	C1E—C2E—H2EA	109.0
C11'—C12'—H12'	120.0	C1E—C2E—H2EB	107.7
C16'—C15'—H15'	120.0	H2EA—C2E—H2EB	107.3
C16'—C15'—C14	120.0	C3E—O2E—H2E	100 (5)
C14—C15'—H15'	120.0	C3E—C4E—H4EA	110.4
C15'—C16'—H16'	120.0	C3E—C4E—H4EB	108.9
C15'—C16'—C17	120.0	C3E—C4E—H4EC	109.3
C17—C16'—H16'	120.0	H4EA—C4E—H4EB	109.4
O1—C17—C16'	119.5 (12)	H4EA—C4E—H4EC	109.4
O1—C17—C16	120.4 (12)	H4EB—C4E—H4EC	109.4
C16'—C17—C16	120.0	H6EA—C6E—H6EB	107.2
C17—C16—H16	120.0	O3E—C6E—H6EA	108.2
C15—C16—C17	120.0	O3E—C6E—H6EB	107.6
C15—C16—H16	120.0	O3E—C6E—C5E	118 (3)
C16—C15—H15	120.0	C5E—C6E—H6EA	106.8
C14—C15—C16	120.0	C5E—C6E—H6EB	108.3
C14—C15—H15	120.0	C6E—O3E—H3E	109.2
C15'—C14—N1	120 (2)	C6E—C5E—H5EA	110.2
C15—C14—N1	120 (2)	C6E—C5E—H5EB	108.6
C15—C14—C15'	120.0	C6E—C5E—H5EC	109.9
C13—C8—C1	115 (2)	H5EA—C5E—H5EB	109.5
C13—C8—C9	120.0	H5EA—C5E—H5EC	109.4
C9—C8—C1	125 (2)	H5EB—C5E—H5EC	109.3
C8—C13—H13	120.0	H8EA—C8E—H8EB	107.2
C8—C13—C12	120.0	C7E—C8E—H8EA	108.6
C12—C13—H13	120.0	C7E—C8E—H8EB	107.9
C13—C12—H12	120.0	O4E—C8E—H8EA	107.5
C13—C12—C11	120.0	O4E—C8E—H8EB	107.8
C11—C12—H12	120.0	O4E—C8E—C7E	117 (3)
C12—C11—H11	120.0	C8E—C7E—H7EA	110.9
C10—C11—C12	120.0	C8E—C7E—H7EB	109.8
C10—C11—H11	120.0	C8E—C7E—H7EC	110.0
C11—C10—H10	120.0	H7EA—C7E—H7EB	108.8
C11—C10—C9	120.0	H7EA—C7E—H7EC	108.6
C9—C10—H10	120.0	H7EB—C7E—H7EC	108.7
C8—C9—H9	120.0	C8E—O4E—H4E	121 (10)
C10—C9—C8	120.0	O1W^i—O1W—O1W^ii	60.00 (2)
C10—C9—H9	120.0
C3—C2—C1—N1	11 (7)	C9'—C10'—C11'—C12'	0.0
C3—C2—C1—C8	179 (4)	C10'—C11'—C12'—C13'	0.0
C3—C4—C5'—C6'	180 (3)	C12'—C13'—C8'—C1'	−174 (2)
C2—C3—C2'—C1'	15 (8)	C12'—C13'—C8'—C9'	0.0
C2—C3—C4—C5	21 (6)	O1—C17—C16—C15	179 (2)
C2—C3—C4—C5'	−159 (4)	C15'—C16'—C17—O1	−179 (2)
C2—C1—N1—C1'	−9 (7)	C15'—C16'—C17—C16	0.0
C2—C1—N1—C14	178 (4)	C16'—C15'—C14—N1	179 (2)
C2—C1—C8—C13	52 (4)	C16'—C15'—C14—C15	0.0
C2—C1—C8—C9	−123 (3)	C16'—C17—C16—C15	0.0
C1—N1—C1'—C2'	12 (7)	C17—C16—C15—C14	0.0
C1—N1—C1'—C8'	−174 (3)	C16—C15—C14—N1	−179 (2)
C1—N1—C14—C15'	59 (4)	C16—C15—C14—C15'	0.0
C1—N1—C14—C15	−122 (3)	C14—N1—C1'—C2'	−176 (3)
C1—C8—C13—C12	−175 (3)	C14—N1—C1'—C8'	−1 (6)
C1—C8—C9—C10	175 (3)	C14—C15'—C16'—C17	0.0
N1—C1—C8—C13	−140 (3)	C8—C1—N1—C1'	−178 (3)
N1—C1—C8—C9	45 (5)	C8—C1—N1—C14	9 (6)
N1—C1'—C2'—C3	−14 (6)	C8—C13—C12—C11	0.0
N1—C1'—C8'—C13'	−133 (3)	C13—C8—C9—C10	0.0
N1—C1'—C8'—C9'	53 (4)	C13—C12—C11—C10	0.0
C1'—N1—C14—C15'	−113 (3)	C12—C11—C10—C9	0.0
C1'—N1—C14—C15	66 (4)	C11—C10—C9—C8	0.0
C1'—C8'—C9'—C10'	174 (2)	C9—C8—C13—C12	0.0
C2'—C3—C2—C1	−13 (8)	C5—C4—C5'—C6'	0.0
C2'—C3—C4—C5	−146 (4)	C4—C3—C2—C1	179 (4)
C2'—C3—C4—C5'	34 (6)	C4—C3—C2'—C1'	−177 (4)
C2'—C1'—C8'—C13'	42 (4)	C4—C5—C6—C7	0.0
C2'—C1'—C8'—C9'	−132 (3)	C4—C5'—C6'—C7	0.0
C13'—C8'—C9'—C10'	0.0	C5'—C6'—C7—C6	0.0
C8'—C1'—C2'—C3	171 (4)	C6'—C7—C6—C5	0.0
C8'—C13'—C12'—C11'	0.0	C6—C5—C4—C3	−180 (3)
C8'—C9'—C10'—C11'	0.0	C6—C5—C4—C5'	0.0

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

4-(2,4,6-triphenylpyridinium-1-yl)-phenolate ethanol solvate (et1_ethanol_0_76gpa)

Crystal data

C29H21NO·4(C2H6O)·O	Dx = 1.198 Mg m^−3
Mr = 599.74	Mo Kα radiation, λ = 0.71073 Å
Trigonal, R3c	Cell parameters from 654 reflections
a = 23.645 (8) Å	θ = 2.5–26.4°
c = 30.91 (2) Å	µ = 0.08 mm^−1
V = 14968 (16) Å^3	T = 293 K
Z = 18	Block, clear red
F(000) = 5796	0.4 × 0.2 × 0.14 mm

Data collection

New Xcalibur, EosS2 diffractometer	504 reflections with I > 2σ(I)
ω scans	Rint = 0.230
Absorption correction: analytical CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	θmax = 26.4°, θmin = 3.3°
Tmin = 0.981, Tmax = 0.992	h = −28→29
5030 measured reflections	k = −20→23
2002 independent reflections	l = −22→23

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.125	w = 1/[σ^2(Fo^2) + (0.1651P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.404	Δρmax = 0.24 e Å^−3
S = 0.95	Δρmin = −0.22 e Å^−3
2002 reflections	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
361 parameters	Absolute structure: Flack x determined using 125 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
462 restraints	Absolute structure parameter: −5.4 (10)

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	−0.002 (2)	0.4780 (16)	0.1182 (13)	0.065 (9)
C1'	−0.024 (2)	0.4385 (15)	0.1546 (15)	0.058 (12)
C2'	−0.024 (3)	0.3807 (17)	0.1506 (17)	0.067 (13)
H2'	−0.042456	0.350714	0.173107	0.080*
C3	0.000 (3)	0.364 (2)	0.1155 (17)	0.083 (12)
C2	0.030 (2)	0.4076 (14)	0.0820 (18)	0.067 (14)
H2	0.045848	0.397287	0.057460	0.080*
C1	0.035 (2)	0.4681 (16)	0.0875 (15)	0.071 (15)
C13'	−0.0546 (15)	0.4388 (16)	0.2263 (15)	0.073 (13)
H13'	−0.022554	0.427889	0.231899	0.088*
C8'	−0.0637 (17)	0.4542 (16)	0.1845 (13)	0.066 (11)
C9'	−0.112 (2)	0.4705 (16)	0.1761 (13)	0.076 (15)
H9'	−0.117674	0.480854	0.148147	0.092*
C10'	−0.1504 (14)	0.4713 (16)	0.2097 (18)	0.092 (17)
H10'	−0.182392	0.482231	0.204079	0.111*
C11'	−0.1412 (17)	0.4559 (16)	0.2515 (16)	0.095 (17)
H11'	−0.167191	0.456438	0.273922	0.115*
C12'	−0.093 (2)	0.4396 (16)	0.2598 (12)	0.078 (14)
H12'	−0.087273	0.429266	0.287833	0.093*
O1	0.006 (3)	0.7163 (15)	0.119 (2)	0.111 (12)
C15'	−0.0284 (18)	0.5567 (12)	0.0870 (13)	0.08 (2)
H15'	−0.048425	0.527031	0.064529	0.101*
C16'	−0.0298 (17)	0.6148 (15)	0.0876 (13)	0.079 (17)
H16'	−0.050686	0.623992	0.065532	0.095*
C17	0.000 (2)	0.6590 (12)	0.1211 (14)	0.084 (14)
C16	0.0314 (17)	0.6452 (14)	0.1541 (13)	0.10 (2)
H16	0.051425	0.674874	0.176531	0.123*
C15	0.0328 (17)	0.5871 (18)	0.1535 (13)	0.055 (14)
H15	0.053687	0.577914	0.175529	0.066*
C14	0.003 (2)	0.5429 (13)	0.1199 (14)	0.064 (12)
C8	0.0623 (16)	0.5082 (15)	0.0476 (13)	0.059 (12)
C13	0.0508 (16)	0.4869 (14)	0.0049 (15)	0.10 (2)
H13	0.019347	0.444097	−0.001441	0.120*
C12	0.0864 (19)	0.530 (2)	−0.0283 (12)	0.13 (2)
H12	0.078710	0.515489	−0.056831	0.158*
C11	0.1334 (15)	0.5938 (19)	−0.0188 (15)	0.082 (19)
H11	0.157234	0.622370	−0.040960	0.098*
C10	0.1449 (13)	0.6150 (12)	0.0239 (17)	0.072 (18)
H10	0.176397	0.657860	0.030300	0.087*
C9	0.1094 (18)	0.5722 (18)	0.0571 (13)	0.070 (15)
H9	0.117034	0.586469	0.085690	0.084*
C5	0.0487 (17)	0.2933 (13)	0.0958 (15)	0.095 (16)
H5	0.083826	0.329442	0.083058	0.114*
C4	−0.001 (2)	0.2995 (13)	0.1157 (16)	0.078 (12)
C5'	−0.0531 (18)	0.2455 (18)	0.1347 (15)	0.095 (15)
H5'	−0.086081	0.249691	0.147976	0.114*
C6'	−0.0562 (17)	0.1852 (13)	0.1339 (15)	0.090 (15)
H6'	−0.091292	0.149086	0.146585	0.108*
C7	−0.007 (2)	0.1790 (13)	0.1140 (17)	0.086 (11)
H7	−0.008946	0.138658	0.113431	0.103*
C6	0.0456 (18)	0.2330 (18)	0.0950 (17)	0.107 (16)
H6	0.078613	0.228835	0.081667	0.128*
O1E	−0.1394 (18)	0.402 (2)	0.078 (2)	0.16 (2)
H1E	−0.115119	0.395675	0.062577	0.235*
C1E	−0.216 (3)	0.435 (4)	0.074 (3)	0.20 (4)
H1EA	−0.263081	0.410312	0.072696	0.307*
H1EB	−0.200642	0.475522	0.059087	0.307*
H1EC	−0.202126	0.442456	0.103351	0.307*
C3E	−0.134 (4)	0.283 (3)	0.043 (2)	0.22 (4)
H3EA	−0.104426	0.267777	0.053353	0.259*
H3EB	−0.152097	0.292239	0.068362	0.259*
C2E	−0.191 (3)	0.399 (3)	0.054 (2)	0.16 (3)
H2EA	−0.225655	0.353737	0.050341	0.191*
H2EB	−0.175507	0.416518	0.024902	0.191*
O2E	−0.098 (3)	0.340 (2)	0.018 (2)	0.20 (2)
H2E	−0.062 (8)	0.340 (17)	0.010 (4)	0.302*
C4E	−0.184 (3)	0.234 (3)	0.018 (3)	0.19 (3)
H4EA	−0.219554	0.205892	0.036508	0.279*
H4EB	−0.167516	0.208976	0.003709	0.279*
H4EC	−0.197948	0.253982	−0.002905	0.279*
C6E	0.196 (3)	0.584 (3)	0.170 (3)	0.16 (3)
H6EA	0.215887	0.573152	0.145703	0.196*
H6EB	0.218408	0.582682	0.196084	0.196*
O3E	0.129 (2)	0.537 (2)	0.173 (2)	0.18 (3)
H3E	0.120784	0.521399	0.197055	0.270*
C5E	0.205 (3)	0.646 (2)	0.164 (3)	0.19 (3)
H5EA	0.244654	0.677608	0.178015	0.291*
H5EB	0.168709	0.647753	0.176439	0.291*
H5EC	0.207673	0.655681	0.133692	0.291*
C8E	0.139 (3)	0.403 (3)	0.200 (3)	0.20 (3)
H8EA	0.136992	0.395322	0.169549	0.240*
H8EB	0.120265	0.361553	0.215264	0.240*
C7E	0.204 (3)	0.444 (4)	0.213 (4)	0.24 (3)
H7EA	0.205053	0.458165	0.242519	0.366*
H7EB	0.224879	0.480596	0.194484	0.366*
H7EC	0.226735	0.419379	0.212112	0.366*
O4E	0.103 (3)	0.436 (3)	0.2110 (19)	0.21 (3)
H4E	0.103 (11)	0.433 (11)	0.240 (2)	0.318*
O2W	0.333333	0.666667	0.055 (7)	0.27 (7)*
O3W	−0.333333	0.333333	−0.044 (11)	0.40 (5)*
O1W	−0.299 (4)	0.359 (4)	0.170 (6)	0.08 (4)*	0.3333

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.07 (2)	0.07 (2)	0.08 (2)	0.05 (2)	0.003 (16)	0.012 (19)
C1'	0.07 (3)	0.05 (2)	0.05 (2)	0.02 (2)	−0.03 (2)	−0.019 (17)
C2'	0.073 (19)	0.061 (15)	0.074 (19)	0.039 (14)	−0.009 (12)	0.006 (11)
C3	0.10 (3)	0.08 (3)	0.09 (3)	0.05 (3)	0.00 (2)	0.00 (2)
C2	0.07 (3)	0.06 (2)	0.08 (4)	0.03 (3)	−0.02 (3)	−0.01 (2)
C1	0.07 (3)	0.044 (19)	0.08 (3)	0.02 (2)	0.01 (2)	−0.010 (19)
C13'	0.080 (18)	0.067 (19)	0.068 (15)	0.033 (13)	0.004 (11)	0.003 (12)
C8'	0.066 (16)	0.055 (17)	0.067 (15)	0.022 (12)	−0.004 (11)	−0.003 (11)
C9'	0.09 (3)	0.05 (4)	0.09 (3)	0.04 (3)	0.01 (2)	0.01 (3)
C10'	0.09 (2)	0.09 (2)	0.09 (2)	0.042 (16)	0.006 (12)	−0.006 (13)
C11'	0.12 (4)	0.09 (4)	0.08 (3)	0.05 (4)	−0.01 (3)	−0.04 (3)
C12'	0.11 (4)	0.03 (3)	0.08 (2)	0.02 (3)	0.01 (2)	−0.01 (3)
O1	0.18 (3)	0.06 (2)	0.11 (4)	0.07 (3)	0.01 (2)	0.03 (3)
C15'	0.10 (4)	0.05 (3)	0.10 (4)	0.04 (3)	−0.03 (3)	0.00 (3)
C16'	0.09 (4)	0.04 (3)	0.10 (4)	0.03 (3)	0.01 (3)	0.02 (2)
C17	0.10 (3)	0.04 (3)	0.11 (4)	0.03 (3)	0.00 (2)	0.02 (3)
C16	0.14 (5)	0.09 (3)	0.10 (4)	0.08 (4)	−0.01 (3)	0.00 (3)
C15	0.06 (3)	0.07 (3)	0.04 (4)	0.04 (3)	0.04 (2)	0.02 (2)
C14	0.07 (3)	0.07 (2)	0.06 (3)	0.05 (2)	0.019 (18)	0.015 (19)
C8	0.07 (3)	0.045 (19)	0.08 (3)	0.04 (2)	0.01 (2)	−0.008 (17)
C13	0.13 (4)	0.08 (3)	0.08 (3)	0.04 (3)	0.02 (3)	−0.01 (2)
C12	0.12 (5)	0.12 (4)	0.08 (3)	0.00 (3)	0.00 (3)	0.00 (3)
C11	0.05 (3)	0.10 (3)	0.08 (4)	0.03 (3)	0.03 (3)	−0.01 (3)
C10	0.09 (3)	0.05 (2)	0.08 (4)	0.03 (2)	0.01 (3)	0.00 (2)
C9	0.10 (4)	0.04 (2)	0.08 (4)	0.04 (2)	0.02 (3)	0.00 (2)
C5	0.11 (3)	0.073 (19)	0.11 (4)	0.05 (2)	0.04 (2)	0.00 (2)
C4	0.07 (2)	0.07 (2)	0.10 (4)	0.04 (2)	0.013 (18)	0.01 (2)
C5'	0.09 (2)	0.07 (2)	0.13 (4)	0.04 (2)	0.03 (2)	0.02 (3)
C6'	0.10 (2)	0.076 (19)	0.10 (4)	0.053 (19)	0.01 (2)	0.02 (2)
C7	0.102 (16)	0.073 (14)	0.094 (19)	0.052 (12)	−0.005 (12)	0.000 (13)
C6	0.14 (3)	0.08 (2)	0.11 (4)	0.06 (2)	0.04 (2)	−0.01 (2)
O1E	0.09 (3)	0.16 (4)	0.24 (7)	0.08 (3)	0.02 (3)	0.00 (4)
C1E	0.08 (4)	0.28 (7)	0.29 (10)	0.12 (4)	−0.02 (5)	−0.08 (6)
C3E	0.20 (6)	0.21 (5)	0.18 (7)	0.06 (4)	0.00 (5)	−0.01 (4)
C2E	0.06 (4)	0.16 (5)	0.24 (7)	0.05 (3)	0.00 (4)	−0.04 (4)
O2E	0.21 (3)	0.17 (3)	0.18 (4)	0.07 (2)	0.01 (2)	−0.03 (2)
C4E	0.16 (6)	0.17 (4)	0.22 (9)	0.08 (3)	−0.01 (5)	−0.01 (5)
C6E	0.16 (3)	0.17 (3)	0.17 (3)	0.082 (17)	−0.001 (14)	−0.004 (14)
O3E	0.14 (3)	0.18 (3)	0.21 (7)	0.08 (2)	−0.06 (3)	0.00 (4)
C5E	0.21 (4)	0.18 (3)	0.19 (4)	0.10 (2)	0.01 (3)	0.01 (2)
C8E	0.19 (4)	0.22 (4)	0.20 (4)	0.10 (3)	0.02 (2)	0.01 (3)
C7E	0.22 (4)	0.26 (5)	0.25 (6)	0.11 (3)	−0.04 (4)	−0.01 (5)
O4E	0.23 (3)	0.22 (4)	0.20 (5)	0.13 (3)	0.09 (3)	0.07 (3)

Geometric parameters (Å, º)

N1—C1'	1.39 (3)	C5—H5	0.9300
N1—C1	1.39 (3)	C5—C4	1.3900
N1—C14	1.48 (3)	C5—C6	1.3900
C1'—C2'	1.37 (2)	C4—C5'	1.3900
C1'—C8'	1.49 (3)	C5'—H5'	0.9300
C2'—H2'	0.9300	C5'—C6'	1.3900
C2'—C3	1.39 (2)	C6'—H6'	0.9300
C3—C2	1.38 (2)	C6'—C7	1.3900
C3—C4	1.50 (3)	C7—H7	0.9300
C2—H2	0.9300	C7—C6	1.3900
C2—C1	1.39 (2)	C6—H6	0.9300
C1—C8	1.49 (3)	O1E—H1E	0.8242
C13'—H13'	0.9300	O1E—C2E	1.42 (4)
C13'—C8'	1.3900	C1E—H1EA	0.9631
C13'—C12'	1.3900	C1E—H1EB	0.9629
C8'—C9'	1.3900	C1E—H1EC	0.9629
C9'—H9'	0.9300	C1E—C2E	1.40 (4)
C9'—C10'	1.3900	C3E—H3EA	0.9700
C10'—H10'	0.9300	C3E—H3EB	0.9700
C10'—C11'	1.3900	C3E—O2E	1.42 (4)
C11'—H11'	0.9300	C3E—C4E	1.40 (4)
C11'—C12'	1.3900	C2E—H2EA	0.9700
C12'—H12'	0.9300	C2E—H2EB	0.9700
O1—C17	1.29 (2)	O2E—H2E	0.891 (13)
C15'—H15'	0.9300	C4E—H4EA	0.9602
C15'—C16'	1.3900	C4E—H4EB	0.9602
C15'—C14	1.3900	C4E—H4EC	0.9602
C16'—H16'	0.9300	C6E—H6EA	0.9700
C16'—C17	1.3900	C6E—H6EB	0.9700
C17—C16	1.3900	C6E—O3E	1.41 (3)
C16—H16	0.9300	C6E—C5E	1.40 (4)
C16—C15	1.3900	O3E—H3E	0.8200
C15—H15	0.9300	C5E—H5EA	0.9883
C15—C14	1.3900	C5E—H5EB	0.9909
C8—C13	1.3900	C5E—H5EC	0.9862
C8—C9	1.3900	C8E—H8EA	0.9700
C13—H13	0.9300	C8E—H8EB	0.9700
C13—C12	1.3900	C8E—C7E	1.40 (4)
C12—H12	0.9300	C8E—O4E	1.44 (3)
C12—C11	1.3900	C7E—H7EA	0.9604
C11—H11	0.9300	C7E—H7EB	0.9604
C11—C10	1.3900	C7E—H7EC	0.9604
C10—H10	0.9300	O4E—H4E	0.891 (11)
C10—C9	1.3900	O1W—O1W^i	1.25 (13)
C9—H9	0.9300	O1W—O1W^ii	1.25 (13)
C1'—N1—C14	119 (2)	C4—C5—H5	120.3
C1—N1—C1'	120 (3)	C4—C5—C6	120.0
C1—N1—C14	118 (2)	C6—C5—H5	119.7
N1—C1'—C2'	114 (4)	C5—C4—C3	121 (3)
N1—C1'—C8'	114 (3)	C5—C4—C5'	120.0
C2'—C1'—C8'	128 (4)	C5'—C4—C3	119 (3)
C1'—C2'—H2'	117.5	C4—C5'—H5'	120.0
C1'—C2'—C3	125 (4)	C6'—C5'—C4	120.0
C3—C2'—H2'	117.7	C6'—C5'—H5'	120.0
C2'—C3—C4	120 (2)	C5'—C6'—H6'	120.0
C2—C3—C2'	120 (3)	C7—C6'—C5'	120.0
C2—C3—C4	120 (2)	C7—C6'—H6'	120.0
C3—C2—H2	122.0	C6'—C7—H7	120.0
C3—C2—C1	116 (4)	C6'—C7—C6	120.0
C1—C2—H2	122.4	C6—C7—H7	120.0
N1—C1—C2	122 (4)	C5—C6—H6	120.0
N1—C1—C8	125 (3)	C7—C6—C5	120.0
C2—C1—C8	110 (4)	C7—C6—H6	120.0
C8'—C13'—H13'	120.0	C2E—O1E—H1E	109.7
C8'—C13'—C12'	120.0	H1EA—C1E—H1EB	109.2
C12'—C13'—H13'	120.0	H1EA—C1E—H1EC	109.1
C13'—C8'—C1'	108 (3)	H1EB—C1E—H1EC	109.1
C9'—C8'—C1'	131 (4)	C2E—C1E—H1EA	110.5
C9'—C8'—C13'	120.0	C2E—C1E—H1EB	108.9
C8'—C9'—H9'	120.0	C2E—C1E—H1EC	110.0
C10'—C9'—C8'	120.0	H3EA—C3E—H3EB	108.3
C10'—C9'—H9'	120.0	O2E—C3E—H3EA	109.9
C9'—C10'—H10'	120.0	O2E—C3E—H3EB	109.5
C9'—C10'—C11'	120.0	C4E—C3E—H3EA	109.9
C11'—C10'—H10'	120.0	C4E—C3E—H3EB	110.1
C10'—C11'—H11'	120.0	C4E—C3E—O2E	109 (4)
C10'—C11'—C12'	120.0	O1E—C2E—C1E	110 (4)
C12'—C11'—H11'	120.0	O1E—C2E—H2EA	109.8
C13'—C12'—H12'	120.0	O1E—C2E—H2EB	109.8
C11'—C12'—C13'	120.0	C1E—C2E—H2EA	108.8
C11'—C12'—H12'	120.0	C1E—C2E—H2EB	110.2
C16'—C15'—H15'	120.1	H2EA—C2E—H2EB	108.1
C16'—C15'—C14	120.0	C3E—O2E—H2E	105 (10)
C14—C15'—H15'	119.9	C3E—C4E—H4EA	109.1
C15'—C16'—H16'	120.0	C3E—C4E—H4EB	109.7
C15'—C16'—C17	120.0	C3E—C4E—H4EC	109.7
C17—C16'—H16'	120.0	H4EA—C4E—H4EB	109.4
O1—C17—C16'	120.0 (13)	H4EA—C4E—H4EC	109.5
O1—C17—C16	119.5 (13)	H4EB—C4E—H4EC	109.4
C16'—C17—C16	120.0	H6EA—C6E—H6EB	108.1
C17—C16—H16	120.0	O3E—C6E—H6EA	108.6
C15—C16—C17	120.0	O3E—C6E—H6EB	109.8
C15—C16—H16	120.0	O3E—C6E—C5E	110 (4)
C16—C15—H15	120.0	C5E—C6E—H6EA	110.0
C16—C15—C14	120.0	C5E—C6E—H6EB	110.0
C14—C15—H15	120.0	C6E—O3E—H3E	109.1
C15'—C14—N1	116 (3)	C6E—C5E—H5EA	112.5
C15—C14—N1	124 (3)	C6E—C5E—H5EB	113.5
C15—C14—C15'	120.0	C6E—C5E—H5EC	111.7
C13—C8—C1	128 (3)	H5EA—C5E—H5EB	105.9
C13—C8—C9	120.0	H5EA—C5E—H5EC	106.2
C9—C8—C1	112 (3)	H5EB—C5E—H5EC	106.5
C8—C13—H13	120.0	H8EA—C8E—H8EB	108.3
C8—C13—C12	120.0	C7E—C8E—H8EA	110.1
C12—C13—H13	120.0	C7E—C8E—H8EB	109.4
C13—C12—H12	120.0	O4E—C8E—H8EA	111.0
C13—C12—C11	120.0	O4E—C8E—H8EB	109.6
C11—C12—H12	120.0	O4E—C8E—C7E	108 (4)
C12—C11—H11	120.0	C8E—C7E—H7EA	109.7
C10—C11—C12	120.0	C8E—C7E—H7EB	109.0
C10—C11—H11	120.0	C8E—C7E—H7EC	109.9
C11—C10—H10	120.0	H7EA—C7E—H7EB	109.4
C11—C10—C9	120.0	H7EA—C7E—H7EC	109.4
C9—C10—H10	120.0	H7EB—C7E—H7EC	109.5
C8—C9—H9	120.0	C8E—O4E—H4E	99 (4)
C10—C9—C8	120.0	O1W^i—O1W—O1W^ii	60.00 (3)
C10—C9—H9	120.0
N1—C1'—C2'—C3	6 (9)	C8'—C9'—C10'—C11'	0.0
N1—C1'—C8'—C13'	−150 (4)	C9'—C10'—C11'—C12'	0.0
N1—C1'—C8'—C9'	41 (6)	C10'—C11'—C12'—C13'	0.0
N1—C1—C8—C13	−121 (5)	C12'—C13'—C8'—C1'	−170 (3)
N1—C1—C8—C9	66 (6)	C12'—C13'—C8'—C9'	0.0
C1'—N1—C1—C2	26 (10)	O1—C17—C16—C15	−172 (5)
C1'—N1—C1—C8	−178 (4)	C15'—C16'—C17—O1	172 (5)
C1'—N1—C14—C15'	−128 (4)	C15'—C16'—C17—C16	0.0
C1'—N1—C14—C15	48 (6)	C16'—C15'—C14—N1	176 (3)
C1'—C2'—C3—C2	2 (12)	C16'—C15'—C14—C15	0.0
C1'—C2'—C3—C4	178 (5)	C16'—C17—C16—C15	0.0
C1'—C8'—C9'—C10'	168 (4)	C17—C16—C15—C14	0.0
C2'—C1'—C8'—C13'	53 (6)	C16—C15—C14—N1	−175 (3)
C2'—C1'—C8'—C9'	−116 (5)	C16—C15—C14—C15'	0.0
C2'—C3—C2—C1	2 (11)	C14—N1—C1'—C2'	−177 (5)
C2'—C3—C4—C5	−147 (5)	C14—N1—C1'—C8'	23 (7)
C2'—C3—C4—C5'	36 (7)	C14—N1—C1—C2	−176 (5)
C3—C2—C1—N1	−16 (9)	C14—N1—C1—C8	−21 (8)
C3—C2—C1—C8	−175 (5)	C14—C15'—C16'—C17	0.0
C3—C4—C5'—C6'	178 (4)	C8—C13—C12—C11	0.0
C2—C3—C4—C5	29 (7)	C13—C8—C9—C10	0.0
C2—C3—C4—C5'	−149 (5)	C13—C12—C11—C10	0.0
C2—C1—C8—C13	37 (6)	C12—C11—C10—C9	0.0
C2—C1—C8—C9	−136 (4)	C11—C10—C9—C8	0.0
C1—N1—C1'—C2'	−19 (9)	C9—C8—C13—C12	0.0
C1—N1—C1'—C8'	−179 (4)	C5—C4—C5'—C6'	0.0
C1—N1—C14—C15'	74 (5)	C4—C3—C2—C1	−173 (5)
C1—N1—C14—C15	−110 (4)	C4—C5—C6—C7	0.0
C1—C8—C13—C12	−173 (4)	C4—C5'—C6'—C7	0.0
C1—C8—C9—C10	174 (3)	C5'—C6'—C7—C6	0.0
C13'—C8'—C9'—C10'	0.0	C6'—C7—C6—C5	0.0
C8'—C1'—C2'—C3	163 (6)	C6—C5—C4—C3	−178 (4)
C8'—C13'—C12'—C11'	0.0	C6—C5—C4—C5'	0.0

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