Managing negative linear compressibility and thermal expansion through steric hindrance: a case study of 1,2-bis­­(4′-pyridyl)­ethane cocrystals

Multicomponent crystals have great scientific potential because of their amenability to crystal engineering in terms of composition and structure, and hence their properties can be easily modified. More and more research areas are employing the design of multicomponent materials to improve the known or induce novel physicochemical properties of crystals, and recently they have been explored as materials with abnormal pressure behaviour. The cocrystal of 1,2-bis­(4′-pyridyl)­ethane and fumaric acid (ETYFUM) exhibits a negative linear compressibility behaviour comparable to that of framework and metal-containing materials, but overcomes many of their deficiencies restricting their use. Herein ETYFUM was investigated at low temperature to reveal negative thermal expansion behaviour. Additionally, a cocrystal isostructural with ETYFUM, based on 1,2-bis­(4′-pyridyl)­ethane and succinic acid (ETYSUC), was exposed to high pressure and low temperature, showing that its behaviour is similar in nature to that of ETYFUM, but significantly differs in the magnitude of both effects. It was revealed that the minor structural difference between the acid molecules does not significantly affect the packing under ambient conditions, but has far-reaching consequences when it comes to the deformation of the structure when exposed to external stimuli.

1. Introduction

Multicomponent organic crystals have attracted a lot of interest as their composition, molecular aggregation and intermolecular interactions can be tuned and their synthesis is cost efficient (Ding et al., 2024). They can exhibit fluorescence (Li et al., 2016; Dai et al., 2024), phospho­rescence (Zhou et al., 2020; Qu et al., 2023), light-induced dynamic movement (Li et al., 2020), static photonic properties (Li et al., 2020) and temperature- and pressure-induced proton transfer (Bhunia et al., 2010; Jones et al., 2014; Patyk-Kaźmierczak et al., 2024), or can be means to improve physicochemical properties of active pharmaceutical ingredients (Duggirala et al., 2015; Bolla et al., 2022). Recently, a molecular cocrystal was discovered to exhibit significant negative linear compressibility (NLC) behaviour of a magnitude previously associated with framework materials. This 1:1 cocrystal composed of 1,2-bis­(4′-pyridyl)­ethane (ETY) and fumaric acid (FUM), herein referred to as ETYFUM (Patyk-Kaźmierczak & Kaźmierczak, 2024), has a median compressibility of −24 (1) TPa⁻¹ in the NLC direction and a compressibility capacity (Cairns & Goodwin, 2015), χ_K, equal to 6.8% (for the 0.1 MPa to 3.58 GPa pressure range). Its main advantage is its facile and environmentally friendly synthesis and the recyclability of the building blocks.

Negative compressibility behaviour is unusual, as it is expected that a crystal will respond to an increase in pressure by decreasing its dimensions. However, in rare cases, abnormal behaviour can be observed when a material expands along one (NLC) or two (negative area compressibility, NAC) principal axes (Baughman et al., 1998; Cairns & Goodwin, 2015). However, to make such a process thermodynamically possible, sufficient compression must take place along the remaining principal axes/axis to achieve overall volume reduction (Baughman et al., 1998; Cairns & Goodwin, 2015). On the other hand, there is no such limitation when it comes to negative thermal expansion (NTE), where linear or volumetric contraction can occur on heating (Miller et al., 2009). Materials exhibiting any of the above-mentioned behaviours have many possible applications. The ability to expand under pressure makes NLC and NAC materials applicable as optical sensors or in telecommunication systems required to function under high pressure (Baughman et al., 1998). Meanwhile, NTE materials can be used to compensate for the positive thermal expansion (PTE) of other materials (Takenaka, 2012).

NTE materials have been intensively studied since the mid 1990s, when the NTE behaviour of a variety of materials was explained in relation to their crystal structures (Korthuis et al., 1995; Sleight, 1995; Mary et al., 1996; Evans et al., 1997; Lind, 2012). There are many reports of inorganic and inorganic–organic hybrid materials exhibiting NTE along one or more principal axes; however, the literature on organic NTE crystals is comparably scarce. A study of the Cambridge Structural Database from 2021 (Lee & Dumitrescu, 2021) has revealed that 37% of the deposited structures investigated at various temperatures exhibit NTE (34% axial NTE and 3% volumetric NTE), which is more than was believed. The largest NTE values found in the study reached ca −350 and −200 MK⁻¹, but such cases can be considered outliers. More commonly, uniaxial NTE is in the range of −100 MK⁻¹ (Lee & Dumitrescu, 2021).

When it comes to NLC materials, reports of significant NLC are scarce, with the most negative median compressibility usually associated with framework materials. The most impressive cases are as follows: Ag₃[Co(CN)₆] Phase I [K_NLC = −76 (9) TPa⁻¹; Δp = 0–0.19 GPa (Goodwin et al., 2008)], InH(BCD)₂ [K_NLC = −62.4 TPa⁻¹; Δp = 0–0.53 GPa (Zeng et al., 2017)] and Zn[Au(CN)₂]₂ Phase I [K_NLC = −42 (5) TPa⁻¹; Δp = 0–1.8 GPa (Cairns et al., 2013)]. Recently, density functional theory was used to uncover a massive NLC for the 3D covalent organic framework NPN-3 [K_NLC = −42.04 TPa⁻¹; Δp = 0–0.9 GPa (Erkartal, 2024)].

It has been shown that some topological motifs show clear predisposition to exhibit NLC (Cairns & Goodwin, 2015). Hence, a search of novel NLC materials often focuses on crystals with structures utilizing such motifs, one of which is the wine rack. There are a number of NLC crystals of wine-rack structures reported in the literature, with some of the most recent and interesting cases including the already discussed ETYFUM (Patyk-Kaźmierczak & Kaźmierczak, 2024), MCF-34 (Zeng et al., 2020), Eu[Ag(CN)₂]₃·3H₂O (Liu et al., 2024) and [C(NH₂)₃]Er(HCO₂)₂(C₂O₄) (Hitchings et al., 2024). MCF-34 is a metal–organic framework with two distinctive wine-rack units oriented in four ways in the crystal structure, and is the first case of a multitype wine-rack material investigated in the context of NLC. Its NLC is also significant, with K_NLC = −47.3 (2) TPa⁻¹ in the 0–0.53 GPa range. Meanwhile, Eu[Ag(CN)₂]₃·3H₂O is a framework material that exhibits NLC over a very wide pressure range, 0–8.2 GPa [K_NLC = −4.2 (1) TPa⁻¹]. Lastly, [C(NH₂)₃]Er(HCO₂)₂(C₂O₄) is the first reported case of a hybrid perovskite that exhibits NLC even from ambient pressure [K_NLC = −10.1 (7) TPa⁻¹ for the 0–2.63 (10) GPa range].

The NAC, NLC and NTE associated with changes along the orthogonal principal axes are easily monitored for materials of orthogonal crystal systems (orthorhombic, tetragonal and cubic). In the case of the remaining crystal systems, NLC, NAC and NTE can still be observed in the abnormal changes of the unit-cell parameters; however, to determine the magnitude and direction of each effect, a calculation of the strain along the principal axes is necessary. For instance, in the case of ETYFUM of a monoclinic system, two unit-cell parameters increase on compression although negative compressibility occurs only along one principal axis (Patyk-Kaźmierczak & Kaźmierczak, 2024).

In this work, we present the case of a cocrystal (ETYSUC) of 1,2-bis­(4′-pyridyl)­ethane (ETY) and succinic acid (SUC), the NLC behaviour of which is masked by the decrease of all three unit-cell parameters. Under ambient conditions ETYSUC is isostructural with ETYFUM, however, its response to compression is remarkably different. Finally, the NTEs of ETYSUC and ETYFUM are investigated and compared. The difference in temperature and pressure behaviour of ETYSUC and ETYFUM is rationalized in terms of the subtle structural dissimilarities between SUC and FUM molecules.

2. Experimental

2.1. Cocrystal synthesis

ETYSUC and ETYFUM were synthesized by dissolving 1,2-bis­(4′-pyridyl)­ethane (ETY) and the respective acid (succinic acid – SUC, or fumaric acid – FUM) in a 1:1 molar ratio in hot methanol and leaving the solutions for slow evaporation at room temperature or by solvent-assisted ball milling (see the supporting information for additional details).

2.2. X-ray diffraction experiments

Single-crystal X-ray diffraction experiments were performed using a four-circle X-ray diffractometer equipped with a copper or molybdenum X-ray tube. In all cases, CrysAlisPro (Rigaku Oxford Diffraction, 2020, 2022) was used for data collection, UB-matrix determination, data reduction and absorption correction. High-pressure conditions were provided by mounting the sample crystal in a Merrill–Bassett (Merrill & Bassett, 1974) diamond anvil cell (Fig. S1 of the supporting information). For low-temperature experiments (Figs. S2–S5), a nitrogen-flow attachment from Oxford Cryosystems was used. Crystal structure determination was performed using ShelXS or ShelXT (Sheldrick, 2008, 2015b), while refinement was performed using ShelXL (Sheldrick, 2015a), with the three programs implemented in Olex2 (Dolomanov et al., 2009) as an interface. The crystallographic details for all structures are listed in Tables S1–S16 of the supporting information. Powder X-ray diffraction experiments were performed for ETYSUC crystals obtained from ball-milling synthesis, using the Bruker D8 Advance diffractometer (equipped with a copper X-ray tube). Details on X-ray diffraction experiments and data treatment are provided in the supporting information.

2.3. Principal axis strain and linear coefficient of thermal expansion calculations

The principal axis strain and the linear coefficients of thermal expansion were calculated using the PASCal program (Cliffe & Goodwin, 2012; Lertkiattrakul et al., 2023) available at https://www.pascalapp.co.uk/. For details, see the supporting information.

3. Results and discussion

ETYSUC crystallizes in the monoclinic crystal system, space group I2/a [originally reported in space group C2/c (Braga et al., 2010) but here a non-standard setting was selected to ensure a β angle value closer to 90°]. As mentioned previously, under ambient conditions, it is isostructural with ETYFUM. The only difference between the two structures lies in the structure of the acid molecules because FUM is an unsaturated analogue of SUC. Therefore, it is evident that the difference in the hybridization of α-carbon atoms and the presence of two additional hydrogen atoms in the SUC molecule does not significantly affect the preference for the aggregation of the coformers in the cocrystal. However, this seemingly insignificant difference in molecular structures is behind the drastically different pressure and temperature behaviour of ETYFUM and ETYSUC.

3.1. Pressure-induced phase transition in ETYSUC

Compression of the ETYSUC crystal up to 2.9 GPa results in a decrease in all three unit-cell parameters, and an increase in the β angle from 108.512 (3) to 113.81 (4)° (Fig. 1). Above 2.9 GPa the trend in the pressure dependence of the unit-cell parameters changes, with the a parameter starting to increase on compression between 2.97 and 3.73 GPa, and the slope for the parameters c and b is altered (Fig. 1). Based on this observation, it was established that above 2.9 GPa ETYSUC undergoes a phase transition to Phase I′, without alteration of the crystal symmetry nor a noticeable change in unit-cell parameters. The novel phase is structurally closely related to Phase I and differs only in its response to compression. In comparison, on compression of the ETYFUM crystal up to 3.6 GPa, only monotonic changes are observed and an increase in the length of the a and c lattice parameters and β angle accompanied by a significant decrease of b unit-cell parameter takes place (Fig. 1).

Figure 1 Pressure dependence of the (a) unit-cell volume, (b) β angle and (c) unit-cell parameters for ETYFUM (solid lines) and ETYSUC (dashed and dotted lines). For ETYFUM, various symbols mark different sample crystals investigated under pressure as done in the original work (Patyk-Kaźmierczak & Kaźmierczak, 2024). For ETYSUC, the full symbols and dashed lines are for Phase I, and the empty symbols and dotted lines are for Phase I′. The lower subscripts EF, ES-I and ES-I′ stand for ETYFUM, ETYSUC I and ETYSUC I′, respectively. The vertical dashed–dotted line marks the transition pressure (pc) for the crystal of ETYSUC. Solid and dashed lines in (b) and (c) are to guide the eye only, while in (a) they represent Birch–Murnaghan equations of states (Tables S17, S19 and S22). Insets in (a) show indicatrix plots representing compressibility tensors (with PLC and NLC marked in red and blue, respectively) calculated using PASCal (Cliffe & Goodwin, 2012; Lertkiattrakul et al., 2023) for all data points of ETYFUM, and separately for data points of Phase I and Phase I′ of ETYSUC. The axes in the indicatrix plots show the a, b and c axes of the lattice.

3.2. Negative linear compressibility

It was revealed that ETYSUC exhibits NLC behaviour along a similar, but quite not the same, direction (0.80a − 0.60c, Tables S17 and S18) as ETYFUM (0.73a − 0.68c, Tables S22 and S23), and of a much smaller magnitude. For the 0.1 MPa–2.9 GPa range, the median compressibility, K_NLC, is equal to −5.4 (2) TPa⁻¹ and the compressibility capacity (Cairns & Goodwin, 2015), χ_K, is equal to 1.9% (Table S17, Fig. S14). Such parameters make ETYSUC a material with moderate NLC. The significantly lower magnitude is behind the observed decrease in all three unit-cell parameters, in contrast to two ETYFUM parameters that increase with compression. As the NLC strain axis is to some degree aligned with the diagonal [10−1], its elongation should affect the a and c axes in a similar manner (i.e. leading to an increase in the a and c unit-cell parameters). However, it can be compensated for by an increase of the β angle. The change in β angle for both cocrystals can be considered similar, and in the case of ETYSUC, where the effect of NLC is small, it is sufficient to balance the elongation along the 0.80a − 0.60c direction. Meanwhile, it is insufficient for ETYFUM. After the phase transition, when the direction of the NLC of ETYSUC slightly changes (to 0.81a − 0.59c; Table S19 and Fig. S8) and becomes aligned closer to the a axis, we start to observe a slight increase of the a parameter on compression (Fig. 1). However, for ETYSUC I′, the low number of experimental points and their inconsistency (probably caused by the crystal strain resulting from several compression/decompression runs) affect the calculated compressibility values and their estimated standard deviations (ESDs; Table S19).

As the structure of ETYSUC does not differ significantly between Phases I and I′, the strain along the principal axes was also calculated for the data of Phases I and I′ joined (Tables S20 and S21, Fig. S9). For the combined data, the NLC direction is 0.78a − 0.63c, and the median compressibility in the NLC direction shifts to −4.2 (4) TPa⁻¹, which is unsurprising, as the pressure range is now wider (0.1 MPa–3.73 GPa). At the same time, compressibility values calculated for experimental points of ETYSUC I do not notably differ from the results received when ETYSUC I data were considered separately. Meanwhile, the K_NLC values obtained for Phase I′ became much more reasonable (Tables S20 and S21), supporting the observation of NLC made for Phase I′ on a limited number of data points.

3.2.1. NLC mechanism

The mechanism behind NLC in ETYSUC is the same as in ETYFUM, i.e. originates from the deformation of the wine-rack motif formed by O—H⋯N bonded chains of the ETY and SUC molecules (Fig. 2). Similarly to ETYFUM, there are no classic hinges in the form of metal centres, but the same hinge point can be assigned: an oxygen atom of the carb­oxy­lic group interlocked between two hydrogen atoms of the pyridine ring of ETY (Figs. 2 and S10). To track the changes in the geometry of the wine rack on compression it is sufficient to analyse changes occurring in its fragment. In the case of ETYFUM, a triangle was constructed on three adjacent centroids calculated for triads of atoms O1, C4 and C5, each representing a hinge point [Figs. 2(d), 3 and S10]. The height of the triangle is approximately aligned with the direction of NLC in ETYFUM (0.73a − 0.68c), and is related to the parameter d₁ (side) and the φ angle of the triangle according to equation (1):

When pressure is applied, the wine rack deforms, becoming flatter, resulting in a decrease in the base of the triangle (parameter d₂) and φ angle, while the side of the triangle (d₁) remains almost constant (Fig. 3). Therefore, as compression progresses, the height of the triangle will increase, and as we have reported previously for ETYFUM (Patyk-Kaźmierczak & Kaźmierczak, 2024), this change matches the increase in NLC axis X₃ calculated with PASCal, confirming the deformation of wine rack is the cause standing behind the NLC behaviour.

Figure 2 Fragment of the ETYSUC I structure at (a) 0.1 MPa and 298 K, and (b) 2.90 GPa and 298 K, showing a wine-rack motif formed by the ETY⋯SUC chains. (c) Superposition of the motif at 0.1 MPa (blue) and 2.90 GPa (red) with the indicatrix plot calculated using PASCal for the 0.1 MPa–2.90 GPa range, mapped in the same orientation as the structure (NLC marked in blue, PLC marked in red); black arrows show direction of the chains movement on compression, blue arrows the direction of NLC and red arrows the direction of PLC. (d) Magnification of the fragment of the ETYSUC structure showing three adjacent hinge points (red centroids) with the parameters of the triangle formed by them marked: d1 – side, red dashed lines; d2 – base, green dashed line; h – height, blue dashed line; φ – purple highlight.

Figure 3 Change rate (green axis) for parameters d1, h and φ as a function of pressure (right) and temperature (left). For clarity, magnification of temperature data is given as an insert on the left side of the graph. In the pressure graph/magnification of the temperature graph the change in the length of the NLC axis (X3/X1) for ETYFUM and ETYSUC I, calculated using PASCal, is also included (pink and green open diamond symbols and dashed lines). The rate of change for the parameters d1, h and φ was obtained for the values calculated based on functions fitted to the experimental data (Fig. S14 and S20; Tables S33 and S35).

In the case of ETYSUC I, when we analyse the same motif as in ETYFUM, the φ angle changes by only 9% between 0.1 MPa and 2.9 GPa (compared with a decrease of more than 22% observed for ETYFUM for the 0.1 MPa–3.58 GPa range and 20% for the 0.1 MPa–2.9 GPa range). The smaller change in the φ angle translates into a weaker NLC effect. However, it should be noted that the direction of NLC in ETYSUC is different compared with ETYFUM and is not as closely aligned with the height of the triangle, which can explain the difference in the change rate of h and NLC axis X₃ (Fig. 3). The fact that the NLC behaviour is observed and its mechanism is so strongly related to that observed in ETYFUM confirms that the latter can be used as a blueprint for NLC materials, and also shows the magnitude of the effect can be controlled.

3.2.2. Managing NLC magnitude via steric hindrance

It appears that NLC damping in ETYSUC is mainly caused by a steric hindrance in the form of hydrogen atoms at the α-carbon (C2A), see Fig. S11. For ETYFUM, the pivoting of the chains can take place more freely as the hydrogen atom at the α-carbon (C8, which is an equivalent of the C2A atom in ETYSUC) is placed between the hydrogen atoms of the pyridine rings (Fig. S11). Meanwhile, atoms H5 and H6 of the pyridine ring are facing two hydrogen atoms at C2A in ETYSUC. Interestingly, when the evolution of the distance between the hydrogen atoms of the pyridine ring of ETY and the hydrogen atoms of FUM and SUC with pressure is considered (Fig. S15), we observe that it is quite similar. However, the rapprochement of the hydrogen atoms of ETY and SUC/FUM takes place not only as a result of direct compression of the crystal but also due to the pivoting of the ETY⋯SUC and ETY⋯FUM chains. Therefore, the same rapprochement of hydrogen atoms is achieved in both structures, but in ETYFUM it is associated with a decrease in the φ angle of 22% while in ETYSUC it is only by 9% (Fig. 3). It is hence clear that the distance between the hydrogen atoms of ETY and the respective acid is the limiting factor halting the pivoting of chains and hence controlling the NLC magnitude.

Interestingly, when the transition to ETYSUC I′ occurs, the strain in the form of close proximity between atoms H6 and H2ab at the symmetry-equivalent position at 1/2 + x, −y, z is partially released as the intermolecular distance between the two atoms increases (Fig. S12). It appears that when the distance limit between hydrogen atoms of ETY and SUC was achieved at 2.9 GPa, the structure adapted by changing the direction of NLC, allowing for further non-destructive compression of the crystal and separation of one pair of closely squeezed ETY and SUC hydrogen atoms.

Steric hindrance can also explain the difference in the direction of NLC between ETYFUM and ETYSUC. A slight rotation of the SUC molecule with respect to ETY (considering the ETY/SUC pair bonded by a C—H⋯O1 bond) helps to keep the hydrogen atoms at the α-carbon further away from the H5 and H6 atoms of ETY. As a result, the O—H⋯N bonded chains move with respect to one another in two planes instead of one, like in ETYFUM (Fig. 4). Hence, the deformation of the wine rack is accompanied by slight rotation of ETY⋯SUC chains, making the resultant NLC direction different to ETYFUM, and no longer aligned with the height of the triangle constructed on the centroids calculated for hinge points.

Figure 4 Fragments of the ETYSUC and ETYFUM structures shown along the [010] direction in the pressure ranges 0.1 MPa–3.73 GPa and 0.1 MPa–3.58 GPa, respectively. For each cocrystal, one molecule of ETY was superimposed to constitute a reference point for each structure. Structures at different pressure are marked in varied colours (see the colour scale next to each structure). Red arrows mark the direction of movement of the ETY⋯SUC/FUM chains with respect to the reference ETY molecule on compression.

Lastly, some analogies between steric-hindrance control over NLC magnitude observed by us and previously reported on two hybrid perovskites {of the general formula [A]Er(HCO₂)₂(C₂O₄), where A = [(NH₂)₃C] or [(CH₃)₂NH₂] (Hitchings et al., 2024)} can be drawn. In the work by Hitchings et. al. (2024), only [(NH₂)₃C]Er(HCO₂)₂(C₂O₄) exhibits NLC, despite the wine-rack motif being present in both materials. The reasons behind this include differences in host–guest interactions, resulting from different guest molecules being present in the cavities of the framework. It appears that the presence of (CH₃)₂NH₂ in the openings of the wine rack in [(CH₃)₂NH₂]Er(HCO₂)₂(C₂O₄) caused steric hindrance that prevented hinging and NLC. It shows that ensuring the presence of the structural motifs predisposed to NLC might not be enough to successfully design materials of negative compressibility and additional factors such as steric hindrance need to be considered. On the other hand, it opens the possibilities to modify or avoid NLC in the wine-rack framework materials simply by exchanging guest molecules. Of course, the guest-exchange approach is not applicable to non-framework materials, such as ETYFUM or ETYSUC. In this case, the only possibility to introduce steric hindrance is to modify the wine rack by replacing molecules that form it with more bulky analogues. In the case of ETYFUM and ETYSUC, the difference in FUM and SUC molecules is extremely small, yet sufficient to significantly modify the NLC behaviour of the two materials. We believe that further exploration of the effect of larger substituents at α-carbon atoms on NLC would offer more insight into this matter. Nevertheless, our data and results reported by Hitchings et al. (2024) sufficiently show how the introduction of steric hindrance (either in the form of a guest molecule or structural modification of molecules forming the wine rack) can be employed to control the NLC behaviour of the material with structures utilizing the wine-rack motif, leading to either significant damping of NLC or its annihilation.

3.3. Negative thermal expansion

It has been previously shown that the same effects observed on crystal compression can be achieved by exposing the crystal to low temperature. However, the temperature range that can be applied is limited (with temperatures close to absolute zero being very difficult to achieve experimentally). This affects the magnitude of changes that can be induced by cooling. According to the pressure–temperature correspondence rule, usually the same effects can be achieved on compression to approximately 0.2–0.5 GPa as when the temperature is lowered from 300 to 100 K (Kaźmierczak et al., 2021). Therefore, NLCs of ETYFUM and ETYSUC can be a predictor of the abnormal thermal behaviour of the two cocrystals. We have established that indeed they both exhibit NTE along one principal axis, but some differences in their behaviour can be noted.

In the case of ETYFUM, the direction of NTE (0.72a − 0.69c) is almost exactly the same as for NLC (0.73a − 0.68c); however, it is not observed over the entire investigated temperature range (100–300 K), as PTE was recorded between 100 and 150 K along all three primary axes (Tables S28–S30). Interestingly, when the crystal is gradually cooled (with 5 K steps), the NTE behaviour was observed in the 140–300 K range (Tables S28 and S29, Fig. S18). Still, there is no significant difference in the crystal structure or lattice constants of ETYFUM measured in the 140–300 K and 100–150 K ranges, and the symmetry of the crystal (the crystal system and space group) is preserved. Hence, the ETYFUM form that exists between 100 and 150 K is referenced as ETYFUM-lt (as, similarly to compressed ETYSUC, it is only the response to cooling that changes below 150 K). At the same time, NTE in ETYSUC is observed in the whole 100–300 K temperature range (Tables S24 and S25), regardless of the rate of change of temperature, and the direction of NTE in ETYSUC (0.79a − 0.61c) is also close to the direction of NLC (0.80a − 0.60c).

Similar to NLC, NTE is more significant in ETYFUM than in ETYSUC [with linear coefficients of thermal expansion equal to −39.7 (8) MK⁻¹ and −16.5 (7) MK⁻¹, respectively]. In addition, an increase in the unit-cell parameters on cooling is only observed in the case of ETYFUM, but, unlike NLC, it is recorded for the c unit-cell parameter only, and exclusively in the 300–200 K temperature range (Fig. 5).

Figure 5 Temperature dependence of the (a) unit-cell volume, (b) β angle and (c) unit-cell parameters for ETYFUM sample crystal A (solid and dotted lines) and ETYSUC I sample crystal A (dashed lines). The lower subscripts EF, EF-lt and ES-I stand for ETYFUM, ETYFUM low temperature and ETYSUC Phase I, respectively. The insets in (a) show indicatrix plots representing thermal expansion tensors (PTE and NTE marked in red and blue, respectively) calculated using PASCal (Cliffe & Goodwin, 2012; Lertkiattrakul et al., 2023). The axes in the indicatrix plots show the a, b and c axes of the lattice.

3.3.1. NTE mechanism and magnitude control

The mechanism behind NTE can be linked to the wine-rack motif in a manner similar to that for NLC. In general, on cooling of the ETYFUM and ETYSUC crystals, the φ angle decreases (Fig. 3, S16) while the d₁ parameter remains almost constant, causing the height of the triangle to increase [according to equation (1)], which results in elongation of the crystal along one principal axis (i.e. NTE). Interestingly, the geometry of the wine rack changes in a similar manner on cooling ETYFUM from 150 to 100 K when the crystal exhibits PTE. However, the rate of changes of the φ angle becomes milder while the d₁ parameter starts to decrease more rapidly compared with what is observed when cooling ETYFUM from 300 to 140 K and ETYSUC from 300 to 100 K. As a result, when the ETYFUM crystal is cooled from 150 to 100 K, the height of the triangle starts to decrease, which results in PTE. Moreover, in the case of ETYFUM, the increase in h on cooling (in the 300–140 K range) closely matches the change in the NTE axis (X₁) calculated using PASCal (Fig. 3) which allows us to correlate NTE behaviour with deformation of the wine rack.

Similarly, as observed in the compression experiments, the height of the triangle is not aligned with the NTE axis as closely in ETYSUC as in ETYFUM. In fact, the effect of the temperature on h is similar for both cocrystals, but the increase of h in ETYSUC differs significantly from the change observed for the NTE axis X₃ (see Fig. 3). Hence it appears that the final NTE magnitude might again be affected by displacement of the SUC molecules with respect to ETY, similar to that described for the compressed ETYSUC crystal. Although structural changes on cooling from 300 to 100 K are less noticeable and harder to observe visually, the temperature dependence of C—H⋯O bonds (calculated for the C—H bonds normalized to 1.089 Å to avoid bias caused by refinement of the positions of the hydrogen atoms and the lengths of the C—H bonds varying between structural models) shows that the rotation of SUC molecules with respect to ETY takes place in a manner similar to that observed for the compressed crystal of ETYSUC (Fig. S21). Although the length of both C—H⋯O bonds in ETYFUM decreases at a similar rate, in ETYSUC the length of the C5—H5⋯O1A bond decreases faster than for C6—H6⋯O1A, suggesting that the distance between atoms is affected inconsistently and is not a result of linear contraction, but rather additional rotation of molecules has to take place. As a result, the direction of NTE is affected and deformation of the triangle constructed on centroids calculated for O1, C5 and C6 atoms cannot be directly translated into the magnitude of NTE. It is therefore plausible that the effect coming from the deformation of the wine rack is damped by additional movement of SUC and ETY molecules with respect to one another.

3.4. Effect of pressure and temperature on torsion angles of SUC and FUM

Lastly, we would like to comment on the conformational preference of SUC molecules in ETYSUC crystals. Understandably, the order of the bond between α-carbon atoms affects the flexibility of SUC and FUM molecules. In particular, the double bond in FUM forms a conjugated system with two double carbon–oxygen bonds of carb­oxy­lic groups. As a result, there is tendency for the molecule to be planar, or nearly planar (Pauling, 1960), and it introduces a level of rigidity in the FUM molecules. In SUC the order of all carbon–carbon bonds is one and such restrictions do not apply. Nevertheless, the SUC molecules still take almost completely flat conformation [with an O1a–C1a–C2a–C2a torsion angle of about 6.2 (2)° under ambient conditions]. Despite the ability of SUC molecules to change conformation more freely, it remains resistant to changes in pressure and temperature, and on cooling to 100 K, the torsion angle oscillates in the 6.4 (4)–7.3 (5)° range (Fig. S22). The variation in torsion angle with pressure is more significant (in the 0–12° range, Fig. S22); however, as the quality of structural models is low, these values are accompanied by large ESDs and it is hard to evaluate actual changes in conformation induced by pressure. Meanwhile, the analogous torsion angle of FUM (O1–C7–C8–C8) in ETYFUM is closer to 0° [−3.2 (2)° under ambient conditions] and its response to cooling is even smaller [oscillating between −3.1 (3) and −2.7 (2)° in the 100–300 K range, see Fig. S22]. Similarly to ETYSUC, for high-pressure structural models of ETYFUM, the O1–C7–C8–C8 torsion angle of FUM shows larger variation, with values accompanied by large ESDs, which hinders reliable evaluation of the effect of pressure.

4. Conclusions

Abnormal pressure and temperature behaviour of the organic cocrystal ETYSUC was detected and analysed in the context of the previously reported metal-free NLC material, ETYFUM, which is isostructural to ETYSUC. Interestingly, the NLC and NTE of ETYSUC are completely concealed by the decrease in the unit-cell parameters a, b and c with compression and temperature reduction. Only above 2.9 GPa can an increase of the unit-cell parameter a be observed, and the response of the crystal to pressure changes. Hence, 2.9 GPa is considered a phase transition pressure; however, since there is no drastic change in the crystal structure, the high-pressure phase was labelled ETYSUC I′. Despite the similar molecular aggregation of ETYSUC and ETYFUM, the former exhibits NLC and NTE of significantly smaller magnitude. This can be linked to steric hindrance caused by the close positioning of hydrogen atoms at the α-carbon of SUC to hydrogen atoms H5 and H6 of the pyridine ring of ETY, and the different manner in which the O—H⋯N-bonded chains change their respective positions on compression and cooling in ETYSUC compared with ETYFUM. Despite the lower magnitude of NLC, ETYSUC can still be used as an example, confirming that ETYFUM can be used as a blueprint for the design of metal-free NLC materials. At the same time, it provides additional input to the concept by showing how steric hindrance can dampen the NLC and NTE effects and how the molecular structure needs to be considered when coformers are selected, exemplifying the macroscopic behaviour affected by microscopic modifications.

5. Related literature

The following references are cited in the supporting information: Budzianowski & Katrusiak (2004); Bull et al. (2019); Cai & Katrusiak (2014); Harty et al. (2015); Jiang et al. (2022); Knížek (2021); Macrae et al. (2020); Piermarini et al. (1975); Shephard et al. (2022, 2012); Szafrański (2020); Woodall et al. (2013); Yeung et al. (2017); Zhao et al. (2020).

Supporting information

Computing details

1,2-bis(4-Pyridyl)ethane fumaric acid (etyfum_100k)

Crystal data

C12H12N2·C4H4O4	F(000) = 632
Mr = 300.31	Dx = 1.372 Mg m^−3
Monoclinic, I2/a	Cu Kα radiation, λ = 1.54184 Å
a = 16.6633 (6) Å	Cell parameters from 1744 reflections
b = 4.7294 (2) Å	θ = 4.8–71.9°
c = 19.6488 (7) Å	µ = 0.83 mm^−1
β = 110.091 (4)°	T = 100 K
V = 1454.24 (10) Å^3	Plate, colourless
Z = 4	0.25 × 0.15 × 0.04 mm

Data collection

SuperNova, Single source at offset/far, Atlas diffractometer	1405 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source	1210 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.021
Detector resolution: 10.5384 pixels mm^-1	θmax = 72.5°, θmin = 4.8°
ω scans	h = −19→20
Absorption correction: gaussian CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −5→5
Tmin = 0.699, Tmax = 1.000	l = −23→20
2766 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.032	All H-atom parameters refined
wR(F^2) = 0.087	w = 1/[σ^2(Fo^2) + (0.0434P)^2 + 0.7718P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
1405 reflections	Δρmax = 0.19 e Å^−3
132 parameters	Δρmin = −0.20 e Å^−3
1 restraint

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
C1	0.15976 (8)	0.3997 (3)	0.41402 (7)	0.0213 (3)
H1	0.2201 (10)	0.463 (3)	0.4307 (8)	0.025 (4)*
C2	0.13130 (8)	0.2004 (3)	0.45205 (6)	0.0212 (3)
H2	0.1711 (9)	0.111 (3)	0.4949 (8)	0.025 (4)*
C3	0.04530 (8)	0.1264 (3)	0.42803 (6)	0.0186 (3)
C4	−0.00877 (8)	0.2575 (3)	0.36580 (6)	0.0204 (3)
H4	−0.0706 (9)	0.215 (3)	0.3462 (8)	0.027 (4)*
C5	0.02444 (8)	0.4538 (3)	0.33045 (7)	0.0202 (3)
H5	−0.0126 (9)	0.547 (3)	0.2862 (8)	0.024 (4)*
C6	0.01141 (8)	−0.0783 (3)	0.47017 (7)	0.0208 (3)
H6A	−0.0407 (10)	−0.175 (3)	0.4374 (8)	0.025 (4)*
H6B	0.0565 (9)	−0.221 (4)	0.4942 (8)	0.027 (4)*
N1	0.10748 (6)	0.5249 (2)	0.35404 (5)	0.0198 (3)
C7	0.24227 (7)	0.9748 (3)	0.32059 (6)	0.0192 (3)
C8	0.27288 (8)	1.1997 (3)	0.28212 (7)	0.0200 (3)
H8	0.3295 (10)	1.270 (4)	0.3075 (8)	0.030 (4)*
O1	0.16360 (5)	0.89259 (19)	0.28604 (5)	0.0224 (2)
H1A	0.1446 (13)	0.747 (4)	0.3166 (10)	0.070 (7)*
O2	0.28847 (5)	0.8816 (2)	0.37897 (4)	0.0244 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0174 (6)	0.0225 (7)	0.0237 (6)	−0.0011 (5)	0.0066 (5)	−0.0001 (5)
C2	0.0212 (6)	0.0210 (7)	0.0203 (6)	0.0006 (5)	0.0057 (5)	0.0018 (5)
C3	0.0219 (6)	0.0158 (6)	0.0198 (6)	−0.0011 (5)	0.0094 (5)	−0.0027 (5)
C4	0.0184 (6)	0.0199 (6)	0.0233 (6)	−0.0015 (5)	0.0077 (5)	−0.0018 (5)
C5	0.0199 (6)	0.0191 (6)	0.0205 (6)	0.0001 (5)	0.0056 (5)	0.0009 (5)
C6	0.0231 (6)	0.0177 (6)	0.0229 (6)	−0.0016 (5)	0.0097 (5)	0.0001 (5)
N1	0.0194 (5)	0.0188 (5)	0.0219 (5)	−0.0019 (4)	0.0079 (4)	−0.0002 (4)
C7	0.0180 (6)	0.0185 (6)	0.0214 (6)	0.0001 (5)	0.0071 (5)	−0.0004 (5)
C8	0.0169 (6)	0.0194 (6)	0.0240 (6)	−0.0023 (5)	0.0072 (5)	−0.0006 (5)
O1	0.0178 (4)	0.0232 (5)	0.0238 (4)	−0.0049 (4)	0.0041 (3)	0.0054 (4)
O2	0.0212 (5)	0.0267 (5)	0.0226 (5)	−0.0016 (4)	0.0040 (4)	0.0046 (4)

Geometric parameters (Å, º)

C1—H1	0.991 (15)	C5—N1	1.3424 (15)
C1—C2	1.3837 (18)	C6—C6^i	1.541 (2)
C1—N1	1.3390 (16)	C6—H6A	0.997 (16)
C2—H2	0.973 (15)	C6—H6B	0.998 (16)
C2—C3	1.3906 (17)	C7—C8	1.4925 (18)
C3—C4	1.3907 (17)	C7—O1	1.3111 (14)
C3—C6	1.5046 (17)	C7—O2	1.2231 (15)
C4—H4	0.989 (15)	C8—C8^ii	1.319 (2)
C4—C5	1.3835 (18)	C8—H8	0.963 (16)
C5—H5	0.981 (15)	O1—H1A	1.031 (16)
C2—C1—H1	121.5 (9)	C3—C6—C6^i	110.28 (13)
N1—C1—H1	116.0 (9)	C3—C6—H6A	110.4 (9)
N1—C1—C2	122.43 (11)	C3—C6—H6B	109.3 (9)
C1—C2—H2	120.4 (9)	C6^i—C6—H6A	108.9 (9)
C1—C2—C3	119.50 (11)	C6^i—C6—H6B	107.8 (9)
C3—C2—H2	120.1 (9)	H6A—C6—H6B	110.1 (13)
C2—C3—C6	120.86 (11)	C1—N1—C5	118.36 (11)
C4—C3—C2	117.85 (11)	O1—C7—C8	113.82 (10)
C4—C3—C6	121.23 (11)	O2—C7—C8	121.14 (11)
C3—C4—H4	121.8 (9)	O2—C7—O1	125.03 (11)
C5—C4—C3	119.36 (11)	C7—C8—H8	115.4 (9)
C5—C4—H4	118.8 (9)	C8^ii—C8—C7	123.78 (15)
C4—C5—H5	120.5 (9)	C8^ii—C8—H8	120.8 (10)
N1—C5—C4	122.50 (11)	C7—O1—H1A	110.4 (11)
N1—C5—H5	117.0 (9)
C1—C2—C3—C4	0.24 (18)	C4—C3—C6—C6^i	−91.45 (16)
C1—C2—C3—C6	−176.88 (11)	C4—C5—N1—C1	0.15 (18)
C2—C1—N1—C5	0.19 (19)	C6—C3—C4—C5	177.18 (11)
C2—C3—C4—C5	0.08 (18)	N1—C1—C2—C3	−0.4 (2)
C2—C3—C6—C6^i	85.57 (17)	O1—C7—C8—C8^ii	−2.7 (2)
C3—C4—C5—N1	−0.28 (19)	O2—C7—C8—C8^ii	177.32 (15)

Symmetry codes: (i) −x, −y, −z+1; (ii) −x+1/2, −y+5/2, −z+1/2.

1,2-bis(4-Pyridyl)ethane fumaric acid (etyfum_130k)

Crystal data

C12H12N2·C4H4O4	F(000) = 632
Mr = 300.31	Dx = 1.366 Mg m^−3
Monoclinic, I2/a	Cu Kα radiation, λ = 1.54184 Å
a = 16.6728 (5) Å	Cell parameters from 1742 reflections
b = 4.7388 (1) Å	θ = 4.8–72.3°
c = 19.6680 (6) Å	µ = 0.83 mm^−1
β = 110.024 (3)°	T = 130 K
V = 1460.01 (7) Å^3	Plate, colourless
Z = 4	0.25 × 0.15 × 0.04 mm

Data collection

SuperNova, Single source at offset/far, Atlas diffractometer	1415 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source	1211 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.022
Detector resolution: 10.5384 pixels mm^-1	θmax = 72.4°, θmin = 4.8°
ω scans	h = −19→20
Absorption correction: gaussian CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −5→5
Tmin = 0.699, Tmax = 1.000	l = −23→21
2783 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.035	All H-atom parameters refined
wR(F^2) = 0.097	w = 1/[σ^2(Fo^2) + (0.0535P)^2 + 0.6041P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
1415 reflections	Δρmax = 0.17 e Å^−3
132 parameters	Δρmin = −0.24 e Å^−3
0 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
C1	0.15940 (8)	0.4021 (3)	0.41404 (7)	0.0246 (3)
H1	0.2200 (10)	0.458 (3)	0.4299 (8)	0.027 (4)*
C2	0.13110 (8)	0.2029 (3)	0.45222 (7)	0.0248 (3)
H2	0.1719 (10)	0.115 (3)	0.4955 (8)	0.027 (4)*
C3	0.04532 (8)	0.1273 (3)	0.42815 (6)	0.0211 (3)
C4	−0.00858 (8)	0.2573 (3)	0.36589 (7)	0.0234 (3)
H4	−0.0695 (10)	0.216 (4)	0.3474 (8)	0.028 (4)*
C5	0.02448 (8)	0.4536 (3)	0.33049 (7)	0.0230 (3)
H5	−0.0129 (9)	0.545 (3)	0.2863 (8)	0.023 (4)*
C6	0.01167 (9)	−0.0770 (3)	0.47037 (7)	0.0240 (3)
H6A	−0.0405 (10)	−0.170 (4)	0.4375 (8)	0.028 (4)*
H6B	0.0566 (11)	−0.218 (4)	0.4942 (9)	0.036 (4)*
N1	0.10727 (7)	0.5256 (2)	0.35408 (6)	0.0224 (3)
C7	0.24201 (8)	0.9757 (3)	0.32043 (7)	0.0218 (3)
C8	0.27274 (8)	1.1999 (3)	0.28204 (7)	0.0233 (3)
H8	0.3293 (11)	1.270 (4)	0.3076 (9)	0.034 (4)*
O1	0.16362 (5)	0.8931 (2)	0.28613 (5)	0.0264 (3)
H1A	0.1425 (12)	0.741 (5)	0.3167 (11)	0.062 (6)*
O2	0.28801 (6)	0.8831 (2)	0.37871 (5)	0.0287 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0186 (6)	0.0277 (7)	0.0268 (6)	−0.0023 (5)	0.0069 (5)	0.0014 (5)
C2	0.0240 (6)	0.0262 (7)	0.0232 (6)	0.0001 (5)	0.0067 (5)	0.0029 (5)
C3	0.0249 (6)	0.0188 (6)	0.0224 (6)	−0.0014 (5)	0.0118 (5)	−0.0020 (5)
C4	0.0200 (6)	0.0237 (7)	0.0265 (6)	−0.0025 (5)	0.0082 (5)	−0.0012 (5)
C5	0.0218 (6)	0.0236 (7)	0.0228 (6)	−0.0011 (5)	0.0067 (5)	0.0017 (5)
C6	0.0268 (7)	0.0204 (7)	0.0270 (7)	−0.0021 (5)	0.0122 (5)	0.0005 (5)
N1	0.0219 (5)	0.0224 (6)	0.0238 (5)	−0.0023 (4)	0.0091 (4)	0.0003 (4)
C7	0.0198 (6)	0.0224 (7)	0.0231 (6)	−0.0007 (5)	0.0073 (5)	0.0001 (5)
C8	0.0190 (6)	0.0235 (7)	0.0267 (6)	−0.0037 (5)	0.0069 (5)	0.0000 (5)
O1	0.0205 (5)	0.0292 (5)	0.0269 (5)	−0.0058 (4)	0.0048 (4)	0.0071 (4)
O2	0.0241 (5)	0.0330 (6)	0.0256 (5)	−0.0022 (4)	0.0042 (4)	0.0067 (4)

Geometric parameters (Å, º)

C1—H1	0.987 (16)	C6—C6^i	1.534 (3)
C1—C2	1.3859 (19)	C6—H6A	0.992 (16)
C1—N1	1.3366 (17)	C6—H6B	0.993 (18)
C2—H2	0.982 (16)	N1—H1A	1.49 (2)
C2—C3	1.3908 (18)	C7—C8	1.4919 (19)
C3—C4	1.3904 (18)	C7—O1	1.3086 (15)
C3—C6	1.5036 (18)	C7—O2	1.2218 (16)
C4—H4	0.974 (15)	C8—C8^ii	1.317 (3)
C4—C5	1.3843 (18)	C8—H8	0.964 (17)
C5—H5	0.981 (15)	O1—H1A	1.07 (2)
C5—N1	1.3410 (16)
C2—C1—H1	121.0 (9)	C3—C6—H6A	109.7 (9)
N1—C1—H1	116.6 (9)	C3—C6—H6B	109.3 (10)
N1—C1—C2	122.48 (12)	C6^i—C6—H6A	108.2 (9)
C1—C2—H2	119.7 (9)	C6^i—C6—H6B	107.9 (10)
C1—C2—C3	119.49 (12)	H6A—C6—H6B	111.1 (14)
C3—C2—H2	120.8 (9)	C1—N1—C5	118.38 (11)
C2—C3—C6	120.83 (12)	C1—N1—H1A	119.2 (7)
C4—C3—C2	117.70 (12)	C5—N1—H1A	122.4 (7)
C4—C3—C6	121.39 (11)	O1—C7—C8	114.05 (11)
C3—C4—H4	121.2 (9)	O2—C7—C8	121.09 (11)
C5—C4—C3	119.48 (12)	O2—C7—O1	124.86 (12)
C5—C4—H4	119.3 (9)	C7—C8—H8	115.3 (10)
C4—C5—H5	120.1 (9)	C8^ii—C8—C7	123.79 (15)
N1—C5—C4	122.47 (12)	C8^ii—C8—H8	120.9 (10)
N1—C5—H5	117.4 (9)	C7—O1—H1A	112.0 (10)
C3—C6—C6^i	110.66 (14)
C1—C2—C3—C4	0.10 (19)	C4—C3—C6—C6^i	−91.34 (17)
C1—C2—C3—C6	−176.85 (12)	C4—C5—N1—C1	0.03 (19)
C2—C1—N1—C5	0.3 (2)	C6—C3—C4—C5	177.12 (12)
C2—C3—C4—C5	0.19 (19)	N1—C1—C2—C3	−0.4 (2)
C2—C3—C6—C6^i	85.49 (18)	O1—C7—C8—C8^ii	−2.7 (2)
C3—C4—C5—N1	−0.3 (2)	O2—C7—C8—C8^ii	177.36 (17)

Symmetry codes: (i) −x, −y, −z+1; (ii) −x+1/2, −y+5/2, −z+1/2.

1,2-bis(4-Pyridyl)ethane fumaric acid (etyfum_140k_b)

Crystal data

C12H12N2·C4H4O4	F(000) = 632
Mr = 300.31	Dx = 1.366 Mg m^−3
Monoclinic, I2/a	Cu Kα radiation, λ = 1.54184 Å
a = 16.6842 (6) Å	Cell parameters from 2289 reflections
b = 4.7293 (1) Å	θ = 4.3–71.2°
c = 19.6920 (7) Å	µ = 0.83 mm^−1
β = 110.036 (4)°	T = 140 K
V = 1459.75 (9) Å^3	Block, colourless
Z = 4	0.41 × 0.29 × 0.16 mm

Data collection

New Xcalibur, EosS2 diffractometer	1385 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Cu) X-ray Source	1257 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
Detector resolution: 8.0294 pixels mm^-1	θmax = 71.6°, θmin = 4.8°
ω scans	h = −20→19
Absorption correction: gaussian CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −5→3
Tmin = 0.788, Tmax = 0.899	l = −23→24
4110 measured reflections

Refinement

Refinement on F^2	1 restraint
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.040	All H-atom parameters refined
wR(F^2) = 0.115	w = 1/[σ^2(Fo^2) + (0.083P)^2 + 0.1471P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
1385 reflections	Δρmax = 0.20 e Å^−3
132 parameters	Δρmin = −0.23 e Å^−3

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
C1	0.15924 (7)	0.4026 (3)	0.41421 (7)	0.0257 (3)
H1	0.2195 (9)	0.461 (3)	0.4295 (7)	0.024 (3)*
C2	0.13120 (7)	0.2037 (3)	0.45233 (6)	0.0257 (3)
H2	0.1704 (10)	0.115 (3)	0.4947 (7)	0.028 (4)*
C3	0.04530 (7)	0.1279 (2)	0.42825 (6)	0.0223 (3)
C4	−0.00863 (7)	0.2575 (3)	0.36593 (6)	0.0243 (3)
H4	−0.0686 (8)	0.215 (3)	0.3464 (7)	0.024 (3)*
C5	0.02460 (7)	0.4525 (3)	0.33072 (6)	0.0241 (3)
H5	−0.0121 (9)	0.548 (3)	0.2874 (7)	0.022 (3)*
C6	0.01158 (8)	−0.0771 (3)	0.47021 (6)	0.0252 (3)
H6A	−0.0407 (11)	−0.171 (3)	0.4383 (9)	0.034 (4)*
H6B	0.0552 (10)	−0.220 (4)	0.4940 (8)	0.033 (4)*
N1	0.10716 (6)	0.5255 (2)	0.35427 (5)	0.0235 (3)
C7	0.24203 (7)	0.9762 (2)	0.32039 (6)	0.0228 (3)
C8	0.27258 (7)	1.2002 (3)	0.28217 (6)	0.0246 (3)
H8	0.3259 (10)	1.268 (4)	0.3066 (8)	0.037 (4)*
O1	0.16362 (5)	0.89356 (18)	0.28620 (4)	0.0276 (3)
H1A	0.1479 (14)	0.748 (4)	0.3179 (9)	0.071 (6)*
O2	0.28778 (5)	0.88381 (19)	0.37861 (5)	0.0298 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0212 (6)	0.0295 (7)	0.0275 (6)	−0.0015 (5)	0.0096 (5)	0.0017 (5)
C2	0.0244 (6)	0.0289 (6)	0.0238 (6)	0.0010 (5)	0.0084 (5)	0.0028 (5)
C3	0.0272 (6)	0.0205 (6)	0.0231 (6)	−0.0009 (4)	0.0134 (5)	−0.0029 (4)
C4	0.0222 (6)	0.0254 (6)	0.0267 (6)	−0.0030 (5)	0.0101 (5)	−0.0013 (5)
C5	0.0247 (6)	0.0249 (6)	0.0224 (6)	−0.0008 (5)	0.0079 (5)	0.0015 (5)
C6	0.0308 (6)	0.0221 (6)	0.0265 (6)	−0.0021 (5)	0.0145 (5)	0.0005 (5)
N1	0.0254 (5)	0.0240 (6)	0.0235 (5)	−0.0020 (4)	0.0116 (4)	0.0011 (4)
C7	0.0231 (6)	0.0237 (6)	0.0229 (6)	−0.0007 (5)	0.0096 (4)	−0.0009 (5)
C8	0.0212 (6)	0.0252 (6)	0.0281 (6)	−0.0038 (5)	0.0094 (5)	0.0002 (5)
O1	0.0233 (5)	0.0311 (5)	0.0266 (5)	−0.0059 (3)	0.0063 (4)	0.0075 (3)
O2	0.0260 (5)	0.0349 (5)	0.0260 (5)	−0.0026 (4)	0.0059 (4)	0.0073 (3)

Geometric parameters (Å, º)

C1—H1	0.985 (14)	C5—N1	1.3393 (15)
C1—C2	1.3812 (17)	C6—C6^i	1.539 (2)
C1—N1	1.3353 (16)	C6—H6A	0.987 (17)
C2—H2	0.962 (15)	C6—H6B	0.987 (16)
C2—C3	1.3936 (16)	C7—C8	1.4871 (17)
C3—C4	1.3910 (16)	C7—O1	1.3092 (13)
C3—C6	1.5025 (16)	C7—O2	1.2201 (14)
C4—H4	0.963 (13)	C8—C8^ii	1.319 (2)
C4—C5	1.3791 (17)	C8—H8	0.912 (16)
C5—H5	0.973 (13)	O1—H1A	1.022 (16)
C2—C1—H1	121.7 (8)	C3—C6—C6^i	110.65 (12)
N1—C1—H1	115.8 (8)	C3—C6—H6A	110.8 (9)
N1—C1—C2	122.54 (11)	C3—C6—H6B	110.5 (9)
C1—C2—H2	120.8 (9)	C6^i—C6—H6A	107.4 (9)
C1—C2—C3	119.39 (11)	C6^i—C6—H6B	107.5 (9)
C3—C2—H2	119.8 (9)	H6A—C6—H6B	109.9 (12)
C2—C3—C6	120.94 (11)	C1—N1—C5	118.32 (10)
C4—C3—C2	117.75 (11)	O1—C7—C8	114.07 (10)
C4—C3—C6	121.24 (11)	O2—C7—C8	121.21 (10)
C3—C4—H4	121.9 (8)	O2—C7—O1	124.72 (11)
C5—C4—C3	119.23 (11)	C7—C8—H8	115.2 (10)
C5—C4—H4	118.9 (8)	C8^ii—C8—C7	123.94 (14)
C4—C5—H5	120.6 (8)	C8^ii—C8—H8	120.9 (10)
N1—C5—C4	122.77 (11)	C7—O1—H1A	107.9 (12)
N1—C5—H5	116.7 (8)
C1—C2—C3—C4	0.23 (17)	C4—C3—C6—C6^i	−91.82 (16)
C1—C2—C3—C6	−177.03 (11)	C4—C5—N1—C1	0.31 (18)
C2—C1—N1—C5	0.22 (19)	C6—C3—C4—C5	177.51 (10)
C2—C3—C4—C5	0.26 (17)	N1—C1—C2—C3	−0.49 (19)
C2—C3—C6—C6^i	85.34 (16)	O1—C7—C8—C8^ii	−3.3 (2)
C3—C4—C5—N1	−0.55 (19)	O2—C7—C8—C8^ii	177.06 (15)

Symmetry codes: (i) −x, −y, −z+1; (ii) −x+1/2, −y+5/2, −z+1/2.

1,2-bis(4-Pyridyl)ethane fumaric acid (etyfum_145k_b)

Crystal data

C12H12N2·C4H4O4	F(000) = 632
Mr = 300.31	Dx = 1.365 Mg m^−3
Monoclinic, I2/a	Cu Kα radiation, λ = 1.54184 Å
a = 16.6876 (7) Å	Cell parameters from 2278 reflections
b = 4.7329 (2) Å	θ = 4.3–71.2°
c = 19.6859 (9) Å	µ = 0.82 mm^−1
β = 110.002 (5)°	T = 145 K
V = 1461.02 (12) Å^3	Block, colourless
Z = 4	0.41 × 0.29 × 0.16 mm

Data collection

New Xcalibur, EosS2 diffractometer	1394 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Cu) X-ray Source	1262 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
Detector resolution: 8.0294 pixels mm^-1	θmax = 71.6°, θmin = 4.8°
ω scans	h = −20→19
Absorption correction: gaussian CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −5→3
Tmin = 0.849, Tmax = 0.930	l = −23→24
4130 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	All H-atom parameters refined
wR(F^2) = 0.118	w = 1/[σ^2(Fo^2) + (0.079P)^2 + 0.3412P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
1394 reflections	Δρmax = 0.19 e Å^−3
132 parameters	Δρmin = −0.22 e Å^−3
1 restraint

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
C1	0.15925 (8)	0.4027 (3)	0.41426 (7)	0.0267 (3)
C2	0.13110 (8)	0.2044 (3)	0.45239 (7)	0.0268 (3)
C3	0.04539 (8)	0.1282 (3)	0.42826 (6)	0.0233 (3)
C4	−0.00851 (8)	0.2575 (3)	0.36592 (7)	0.0251 (3)
C5	0.02465 (8)	0.4528 (3)	0.33077 (7)	0.0251 (3)
C6	0.01164 (8)	−0.0771 (3)	0.47028 (7)	0.0261 (3)
N1	0.10719 (7)	0.5258 (2)	0.35427 (5)	0.0243 (3)
C7	0.24189 (7)	0.9764 (3)	0.32046 (6)	0.0237 (3)
C8	0.27263 (8)	1.2002 (3)	0.28214 (7)	0.0254 (3)
O1	0.16369 (5)	0.89356 (19)	0.28625 (5)	0.0286 (3)
O2	0.28776 (6)	0.8840 (2)	0.37861 (5)	0.0310 (3)
H5	−0.0132 (9)	0.546 (3)	0.2874 (8)	0.025 (4)*
H2	0.1721 (10)	0.117 (3)	0.4957 (8)	0.030 (4)*
H6A	−0.0399 (10)	−0.169 (3)	0.4388 (9)	0.030 (4)*
H8	0.3266 (10)	1.269 (4)	0.3065 (8)	0.033 (4)*
H6B	0.0553 (10)	−0.219 (4)	0.4942 (8)	0.037 (4)*
H1	0.2198 (9)	0.459 (3)	0.4301 (8)	0.026 (4)*
H4	−0.0701 (9)	0.215 (3)	0.3460 (7)	0.027 (4)*
H1A	0.1455 (13)	0.752 (4)	0.3175 (10)	0.073 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0220 (6)	0.0303 (7)	0.0286 (6)	−0.0014 (5)	0.0098 (5)	0.0024 (5)
C2	0.0258 (6)	0.0298 (7)	0.0250 (6)	0.0014 (5)	0.0088 (5)	0.0035 (5)
C3	0.0289 (6)	0.0212 (6)	0.0240 (6)	−0.0008 (5)	0.0144 (5)	−0.0026 (4)
C4	0.0228 (6)	0.0258 (7)	0.0280 (6)	−0.0022 (5)	0.0105 (5)	−0.0006 (5)
C5	0.0258 (6)	0.0263 (6)	0.0233 (6)	−0.0004 (5)	0.0086 (5)	0.0017 (5)
C6	0.0313 (7)	0.0230 (6)	0.0278 (7)	−0.0033 (5)	0.0150 (5)	−0.0001 (5)
N1	0.0264 (6)	0.0244 (6)	0.0244 (5)	−0.0020 (4)	0.0117 (4)	0.0015 (4)
C7	0.0239 (6)	0.0247 (6)	0.0239 (6)	−0.0007 (5)	0.0098 (5)	−0.0010 (5)
C8	0.0221 (6)	0.0258 (6)	0.0287 (6)	−0.0039 (5)	0.0093 (5)	−0.0002 (5)
O1	0.0245 (5)	0.0315 (5)	0.0278 (5)	−0.0063 (4)	0.0065 (4)	0.0077 (4)
O2	0.0274 (5)	0.0363 (6)	0.0270 (5)	−0.0029 (4)	0.0063 (4)	0.0069 (4)

Geometric parameters (Å, º)

C1—C2	1.3806 (18)	C5—H5	0.978 (15)
C1—N1	1.3367 (16)	C6—C6^i	1.538 (2)
C1—H1	0.987 (15)	C6—H6A	0.974 (16)
C2—C3	1.3916 (17)	C6—H6B	0.984 (18)
C2—H2	0.983 (15)	C7—C8	1.4895 (18)
C3—C4	1.3909 (17)	C7—O1	1.3073 (14)
C3—C6	1.5049 (17)	C7—O2	1.2200 (15)
C4—C5	1.3789 (18)	C8—C8^ii	1.319 (3)
C4—H4	0.987 (14)	C8—H8	0.923 (16)
C5—N1	1.3396 (15)	O1—H1A	1.023 (16)
C2—C1—H1	120.9 (9)	C3—C6—C6^i	110.56 (13)
N1—C1—C2	122.51 (11)	C3—C6—H6A	110.7 (9)
N1—C1—H1	116.6 (9)	C3—C6—H6B	110.4 (10)
C1—C2—C3	119.45 (11)	C6^i—C6—H6A	107.4 (9)
C1—C2—H2	119.5 (9)	C6^i—C6—H6B	107.4 (9)
C3—C2—H2	121.1 (9)	H6A—C6—H6B	110.3 (13)
C2—C3—C6	120.93 (11)	C1—N1—C5	118.26 (11)
C4—C3—C2	117.78 (11)	O1—C7—C8	114.11 (11)
C4—C3—C6	121.23 (11)	O2—C7—C8	121.07 (11)
C3—C4—H4	122.2 (9)	O2—C7—O1	124.82 (11)
C5—C4—C3	119.22 (12)	C7—C8—H8	115.5 (10)
C5—C4—H4	118.6 (9)	C8^ii—C8—C7	123.82 (15)
C4—C5—H5	119.4 (9)	C8^ii—C8—H8	120.7 (10)
N1—C5—C4	122.77 (11)	C7—O1—H1A	109.6 (12)
N1—C5—H5	117.8 (9)
C1—C2—C3—C4	0.06 (19)	C4—C3—C6—C6^i	−91.81 (17)
C1—C2—C3—C6	−177.17 (11)	C4—C5—N1—C1	0.14 (19)
C2—C1—N1—C5	0.1 (2)	C6—C3—C4—C5	177.41 (11)
C2—C3—C4—C5	0.19 (18)	N1—C1—C2—C3	−0.2 (2)
C2—C3—C6—C6^i	85.33 (17)	O1—C7—C8—C8^ii	−2.9 (2)
C3—C4—C5—N1	−0.3 (2)	O2—C7—C8—C8^ii	177.02 (16)

Symmetry codes: (i) −x, −y, −z+1; (ii) −x+1/2, −y+5/2, −z+1/2.

1,2-bis(4-Pyridyl)ethane fumaric acid (etyfum_150k_b)

Crystal data

C12H12N2·C4H4O4	F(000) = 632
Mr = 300.31	Dx = 1.364 Mg m^−3
Monoclinic, I2/a	Cu Kα radiation, λ = 1.54184 Å
a = 16.6834 (8) Å	Cell parameters from 2251 reflections
b = 4.7362 (2) Å	θ = 4.3–71.2°
c = 19.6927 (10) Å	µ = 0.82 mm^−1
β = 109.981 (6)°	T = 150 K
V = 1462.37 (13) Å^3	Block, colourless
Z = 4	0.41 × 0.29 × 0.16 mm

Data collection

New Xcalibur, EosS2 diffractometer	1396 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Cu) X-ray Source	1277 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
Detector resolution: 8.0294 pixels mm^-1	θmax = 71.5°, θmin = 4.8°
ω scans	h = −20→19
Absorption correction: gaussian CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −5→3
Tmin = 0.787, Tmax = 0.899	l = −23→24
4133 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	All H-atom parameters refined
wR(F^2) = 0.118	w = 1/[σ^2(Fo^2) + (0.0796P)^2 + 0.3683P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
1396 reflections	Δρmax = 0.20 e Å^−3
132 parameters	Δρmin = −0.23 e Å^−3
1 restraint

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
C1	0.15914 (8)	0.4031 (3)	0.41428 (7)	0.0267 (3)
H1	0.2190 (9)	0.462 (3)	0.4305 (8)	0.025 (4)*
C2	0.13113 (8)	0.2048 (3)	0.45243 (7)	0.0267 (3)
H2	0.1725 (10)	0.115 (3)	0.4958 (8)	0.030 (4)*
C3	0.04531 (8)	0.1282 (3)	0.42827 (6)	0.0227 (3)
C4	−0.00846 (8)	0.2576 (3)	0.36597 (7)	0.0250 (3)
H4	−0.0697 (9)	0.214 (4)	0.3465 (7)	0.029 (4)*
C5	0.02469 (8)	0.4526 (3)	0.33073 (7)	0.0252 (3)
H5	−0.0130 (10)	0.548 (3)	0.2867 (8)	0.029 (4)*
C6	0.01172 (8)	−0.0769 (3)	0.47035 (7)	0.0260 (3)
H6A	−0.0403 (10)	−0.168 (3)	0.4388 (9)	0.027 (4)*
H6B	0.0553 (11)	−0.219 (4)	0.4943 (8)	0.036 (4)*
N1	0.10713 (6)	0.5258 (2)	0.35428 (5)	0.0240 (3)
C7	0.24189 (7)	0.9766 (3)	0.32046 (6)	0.0233 (3)
C8	0.27255 (8)	1.1999 (3)	0.28208 (7)	0.0250 (3)
H8	0.3266 (10)	1.270 (4)	0.3069 (8)	0.035 (4)*
O1	0.16365 (5)	0.8935 (2)	0.28623 (5)	0.0288 (3)
H1A	0.1460 (13)	0.749 (4)	0.3170 (10)	0.073 (6)*
O2	0.28764 (6)	0.8841 (2)	0.37852 (5)	0.0314 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0223 (6)	0.0296 (7)	0.0291 (6)	−0.0023 (5)	0.0101 (5)	0.0018 (5)
C2	0.0260 (6)	0.0296 (7)	0.0248 (6)	0.0010 (5)	0.0092 (5)	0.0038 (5)
C3	0.0278 (6)	0.0210 (6)	0.0232 (6)	−0.0016 (5)	0.0136 (5)	−0.0028 (4)
C4	0.0231 (6)	0.0259 (7)	0.0275 (6)	−0.0027 (5)	0.0105 (5)	−0.0007 (5)
C5	0.0255 (6)	0.0268 (6)	0.0231 (6)	−0.0016 (5)	0.0081 (5)	0.0013 (5)
C6	0.0317 (7)	0.0229 (6)	0.0276 (7)	−0.0027 (5)	0.0157 (6)	0.0003 (5)
N1	0.0257 (6)	0.0244 (6)	0.0240 (5)	−0.0020 (4)	0.0113 (4)	0.0012 (4)
C7	0.0236 (6)	0.0242 (6)	0.0236 (6)	−0.0005 (5)	0.0099 (5)	−0.0012 (5)
C8	0.0220 (6)	0.0262 (6)	0.0276 (6)	−0.0034 (5)	0.0097 (5)	0.0006 (5)
O1	0.0247 (5)	0.0323 (6)	0.0275 (5)	−0.0066 (4)	0.0066 (4)	0.0078 (4)
O2	0.0281 (5)	0.0369 (6)	0.0266 (5)	−0.0030 (4)	0.0062 (4)	0.0079 (4)

Geometric parameters (Å, º)

C1—H1	0.979 (15)	C5—N1	1.3383 (16)
C1—C2	1.3801 (18)	C6—C6^i	1.536 (2)
C1—N1	1.3366 (16)	C6—H6A	0.978 (16)
C2—H2	0.991 (15)	C6—H6B	0.986 (18)
C2—C3	1.3936 (17)	C7—C8	1.4884 (18)
C3—C4	1.3904 (17)	C7—O1	1.3084 (14)
C3—C6	1.5039 (17)	C7—O2	1.2188 (15)
C4—H4	0.982 (15)	C8—C8^ii	1.318 (2)
C4—C5	1.3796 (18)	C8—H8	0.927 (16)
C5—H5	0.989 (15)	O1—H1A	1.024 (16)
C2—C1—H1	120.9 (9)	C3—C6—C6^i	110.63 (13)
N1—C1—H1	116.4 (9)	C3—C6—H6A	110.6 (9)
N1—C1—C2	122.62 (11)	C3—C6—H6B	110.7 (10)
C1—C2—H2	119.7 (9)	C6^i—C6—H6A	106.9 (9)
C1—C2—C3	119.39 (11)	C6^i—C6—H6B	107.4 (9)
C3—C2—H2	120.9 (9)	H6A—C6—H6B	110.5 (13)
C2—C3—C6	120.85 (11)	C1—N1—C5	118.25 (11)
C4—C3—C2	117.67 (11)	O1—C7—C8	114.05 (10)
C4—C3—C6	121.42 (11)	O2—C7—C8	121.21 (11)
C3—C4—H4	121.5 (9)	O2—C7—O1	124.74 (11)
C5—C4—C3	119.36 (11)	C7—C8—H8	115.3 (10)
C5—C4—H4	119.1 (9)	C8^ii—C8—C7	124.04 (15)
C4—C5—H5	120.2 (9)	C8^ii—C8—H8	120.6 (10)
N1—C5—C4	122.71 (12)	C7—O1—H1A	109.6 (12)
N1—C5—H5	117.1 (9)
C1—C2—C3—C4	0.03 (19)	C4—C3—C6—C6^i	−91.67 (17)
C1—C2—C3—C6	−177.11 (11)	C4—C5—N1—C1	0.3 (2)
C2—C1—N1—C5	0.1 (2)	C6—C3—C4—C5	177.47 (11)
C2—C3—C4—C5	0.34 (18)	N1—C1—C2—C3	−0.3 (2)
C2—C3—C6—C6^i	85.37 (17)	O1—C7—C8—C8^ii	−2.7 (2)
C3—C4—C5—N1	−0.5 (2)	O2—C7—C8—C8^ii	177.11 (16)

Symmetry codes: (i) −x, −y, −z+1; (ii) −x+1/2, −y+5/2, −z+1/2.

1,2-bis(4-Pyridyl)ethane fumaric acid (etyfum_150k)

Crystal data

C12H12N2·C4H4O4	F(000) = 632
Mr = 300.31	Dx = 1.362 Mg m^−3
Monoclinic, I2/a	Cu Kα radiation, λ = 1.54184 Å
a = 16.6852 (7) Å	Cell parameters from 1712 reflections
b = 4.7457 (2) Å	θ = 3.0–72.2°
c = 19.6763 (7) Å	µ = 0.82 mm^−1
β = 109.949 (4)°	T = 150 K
V = 1464.54 (11) Å^3	Plate, colourless
Z = 4	0.25 × 0.14 × 0.04 mm

Data collection

SuperNova, Single source at offset/far, Atlas diffractometer	1418 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source	1195 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.022
Detector resolution: 10.5384 pixels mm^-1	θmax = 72.3°, θmin = 4.8°
ω scans	h = −19→20
Absorption correction: gaussian CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −5→5
Tmin = 0.697, Tmax = 1.000	l = −23→21
2787 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.035	All H-atom parameters refined
wR(F^2) = 0.100	w = 1/[σ^2(Fo^2) + (0.0561P)^2 + 0.4337P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
1418 reflections	Δρmax = 0.14 e Å^−3
132 parameters	Δρmin = −0.25 e Å^−3
0 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
C1	0.15923 (8)	0.4036 (3)	0.41420 (7)	0.0267 (3)
H1	0.2200 (10)	0.465 (3)	0.4303 (8)	0.028 (4)*
C2	0.13099 (8)	0.2043 (3)	0.45227 (7)	0.0267 (3)
H2	0.1724 (10)	0.118 (4)	0.4959 (9)	0.035 (4)*
C3	0.04536 (8)	0.1284 (3)	0.42826 (7)	0.0227 (3)
C4	−0.00846 (8)	0.2573 (3)	0.36597 (7)	0.0252 (3)
H4	−0.0696 (10)	0.213 (4)	0.3465 (8)	0.031 (4)*
C5	0.02471 (8)	0.4534 (3)	0.33064 (7)	0.0252 (3)
H5	−0.0131 (10)	0.545 (3)	0.2860 (8)	0.027 (4)*
C6	0.01161 (9)	−0.0765 (3)	0.47027 (7)	0.0262 (3)
H6A	−0.0404 (11)	−0.175 (4)	0.4376 (9)	0.034 (4)*
H6B	0.0561 (10)	−0.217 (4)	0.4938 (8)	0.031 (4)*
N1	0.10719 (7)	0.5262 (2)	0.35421 (6)	0.0243 (3)
C7	0.24181 (8)	0.9763 (3)	0.32043 (7)	0.0235 (3)
C8	0.27255 (8)	1.2004 (3)	0.28200 (7)	0.0249 (3)
H8	0.3282 (11)	1.271 (4)	0.3067 (9)	0.035 (4)*
O1	0.16365 (6)	0.8934 (2)	0.28618 (5)	0.0285 (3)
H1A	0.1432 (14)	0.747 (5)	0.3169 (12)	0.076 (7)*
O2	0.28780 (6)	0.8842 (2)	0.37865 (5)	0.0316 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0204 (6)	0.0303 (8)	0.0288 (7)	−0.0023 (5)	0.0077 (5)	0.0016 (5)
C2	0.0253 (7)	0.0288 (7)	0.0255 (6)	0.0001 (5)	0.0079 (5)	0.0037 (5)
C3	0.0262 (6)	0.0209 (7)	0.0238 (6)	−0.0013 (5)	0.0123 (5)	−0.0022 (5)
C4	0.0219 (6)	0.0265 (7)	0.0274 (6)	−0.0027 (5)	0.0086 (5)	−0.0009 (5)
C5	0.0248 (7)	0.0258 (7)	0.0243 (6)	−0.0017 (5)	0.0074 (5)	0.0024 (5)
C6	0.0301 (7)	0.0223 (7)	0.0292 (7)	−0.0027 (5)	0.0138 (6)	0.0006 (5)
N1	0.0246 (6)	0.0240 (6)	0.0256 (5)	−0.0027 (4)	0.0101 (4)	0.0012 (4)
C7	0.0215 (6)	0.0241 (7)	0.0248 (6)	−0.0006 (5)	0.0079 (5)	0.0004 (5)
C8	0.0205 (6)	0.0255 (7)	0.0282 (6)	−0.0035 (5)	0.0077 (5)	0.0010 (5)
O1	0.0224 (5)	0.0319 (6)	0.0281 (5)	−0.0067 (4)	0.0045 (4)	0.0077 (4)
O2	0.0265 (5)	0.0371 (6)	0.0276 (5)	−0.0028 (4)	0.0046 (4)	0.0075 (4)

Geometric parameters (Å, º)

C1—H1	0.998 (16)	C6—C6^i	1.535 (3)
C1—C2	1.3850 (19)	C6—H6A	1.002 (17)
C1—N1	1.3366 (17)	C6—H6B	0.987 (17)
C2—H2	0.989 (17)	N1—H1A	1.52 (2)
C2—C3	1.3906 (18)	C7—C8	1.4936 (19)
C3—C4	1.3900 (18)	C7—O1	1.3076 (15)
C3—C6	1.5045 (18)	C7—O2	1.2216 (16)
C4—H4	0.982 (15)	C8—C8^ii	1.314 (3)
C4—C5	1.3849 (19)	C8—H8	0.951 (17)
C5—H5	0.991 (15)	O1—H1A	1.05 (2)
C5—N1	1.3389 (17)
C2—C1—H1	121.7 (9)	C3—C6—H6A	110.8 (10)
N1—C1—H1	115.8 (9)	C3—C6—H6B	109.3 (9)
N1—C1—C2	122.45 (12)	C6^i—C6—H6A	108.7 (10)
C1—C2—H2	119.2 (10)	C6^i—C6—H6B	107.9 (9)
C1—C2—C3	119.52 (12)	H6A—C6—H6B	109.5 (14)
C3—C2—H2	121.2 (10)	C1—N1—C5	118.34 (11)
C2—C3—C6	120.97 (12)	C1—N1—H1A	118.9 (8)
C4—C3—C2	117.73 (12)	C5—N1—H1A	122.7 (8)
C4—C3—C6	121.25 (12)	O1—C7—C8	114.05 (11)
C3—C4—H4	121.5 (10)	O2—C7—C8	121.02 (12)
C5—C4—C3	119.33 (12)	O2—C7—O1	124.93 (12)
C5—C4—H4	119.2 (9)	C7—C8—H8	115.9 (10)
C4—C5—H5	119.9 (9)	C8^ii—C8—C7	123.84 (15)
N1—C5—C4	122.62 (12)	C8^ii—C8—H8	120.2 (10)
N1—C5—H5	117.4 (9)	C7—O1—H1A	111.4 (12)
C3—C6—C6^i	110.61 (14)
C1—C2—C3—C4	0.3 (2)	C4—C3—C6—C6^i	−91.86 (17)
C1—C2—C3—C6	−176.93 (12)	C4—C5—N1—C1	0.1 (2)
C2—C1—N1—C5	0.3 (2)	C6—C3—C4—C5	177.34 (12)
C2—C3—C4—C5	0.07 (19)	N1—C1—C2—C3	−0.6 (2)
C2—C3—C6—C6^i	85.33 (18)	O1—C7—C8—C8^ii	−2.8 (2)
C3—C4—C5—N1	−0.3 (2)	O2—C7—C8—C8^ii	177.09 (17)

Symmetry codes: (i) −x, −y, −z+1; (ii) −x+1/2, −y+5/2, −z+1/2.

1,2-bis(4-Pyridyl)ethane fumaric acid (etyfum_155k_b)

Crystal data

C12H12N2·C4H4O4	F(000) = 632
Mr = 300.31	Dx = 1.364 Mg m^−3
Monoclinic, I2/a	Cu Kα radiation, λ = 1.54184 Å
a = 16.6821 (8) Å	Cell parameters from 2236 reflections
b = 4.7392 (2) Å	θ = 4.3–71.2°
c = 19.6849 (9) Å	µ = 0.82 mm^−1
β = 109.948 (5)°	T = 155 K
V = 1462.91 (12) Å^3	Block, colourless
Z = 4	0.41 × 0.29 × 0.16 mm

Data collection

New Xcalibur, EosS2 diffractometer	1397 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Cu) X-ray Source	1272 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
Detector resolution: 8.0294 pixels mm^-1	θmax = 71.5°, θmin = 4.8°
ω scans	h = −20→19
Absorption correction: gaussian CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −5→3
Tmin = 0.787, Tmax = 0.899	l = −23→24
4149 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.042	All H-atom parameters refined
wR(F^2) = 0.122	w = 1/[σ^2(Fo^2) + (0.0828P)^2 + 0.2849P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
1397 reflections	Δρmax = 0.18 e Å^−3
132 parameters	Δρmin = −0.24 e Å^−3
0 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
C1	0.15908 (8)	0.4036 (3)	0.41427 (7)	0.0277 (3)
H1	0.2197 (10)	0.461 (3)	0.4296 (8)	0.028 (4)*
C2	0.13106 (8)	0.2050 (3)	0.45238 (7)	0.0279 (3)
H2	0.1720 (10)	0.116 (3)	0.4959 (8)	0.032 (4)*
C3	0.04536 (8)	0.1285 (3)	0.42826 (6)	0.0236 (3)
C4	−0.00836 (8)	0.2576 (3)	0.36596 (7)	0.0258 (3)
H4	−0.0699 (9)	0.215 (4)	0.3461 (7)	0.032 (4)*
C5	0.02476 (8)	0.4529 (3)	0.33076 (7)	0.0261 (3)
H5	−0.0116 (10)	0.548 (3)	0.2874 (8)	0.031 (4)*
C6	0.01167 (9)	−0.0767 (3)	0.47024 (7)	0.0269 (3)
H6A	−0.0394 (11)	−0.170 (3)	0.4391 (9)	0.032 (4)*
H6B	0.0554 (11)	−0.218 (4)	0.4944 (9)	0.039 (4)*
N1	0.10716 (6)	0.5263 (2)	0.35434 (5)	0.0249 (3)
C7	0.24191 (7)	0.9767 (3)	0.32042 (6)	0.0242 (3)
C8	0.27259 (8)	1.2003 (3)	0.28207 (7)	0.0262 (3)
H8	0.3266 (10)	1.265 (4)	0.3068 (8)	0.033 (4)*
O1	0.16368 (5)	0.8937 (2)	0.28625 (5)	0.0298 (3)
H1A	0.1463 (14)	0.744 (5)	0.3176 (11)	0.073 (6)*
O2	0.28758 (6)	0.8844 (2)	0.37851 (5)	0.0324 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0232 (6)	0.0311 (7)	0.0295 (6)	−0.0021 (5)	0.0100 (5)	0.0023 (5)
C2	0.0274 (6)	0.0305 (7)	0.0259 (6)	0.0008 (5)	0.0091 (5)	0.0037 (5)
C3	0.0295 (6)	0.0211 (6)	0.0240 (6)	−0.0009 (5)	0.0143 (5)	−0.0021 (4)
C4	0.0238 (6)	0.0267 (7)	0.0281 (6)	−0.0031 (5)	0.0103 (5)	−0.0009 (5)
C5	0.0267 (6)	0.0275 (6)	0.0237 (6)	−0.0012 (5)	0.0081 (5)	0.0019 (5)
C6	0.0327 (7)	0.0238 (6)	0.0283 (7)	−0.0022 (5)	0.0158 (6)	0.0007 (5)
N1	0.0268 (6)	0.0253 (6)	0.0247 (5)	−0.0022 (4)	0.0115 (4)	0.0018 (4)
C7	0.0244 (6)	0.0244 (6)	0.0246 (6)	−0.0007 (5)	0.0096 (5)	−0.0005 (5)
C8	0.0230 (6)	0.0271 (6)	0.0291 (6)	−0.0039 (5)	0.0097 (5)	0.0004 (5)
O1	0.0249 (5)	0.0333 (6)	0.0289 (5)	−0.0071 (4)	0.0064 (4)	0.0079 (4)
O2	0.0289 (5)	0.0379 (6)	0.0277 (5)	−0.0028 (4)	0.0062 (4)	0.0077 (4)

Geometric parameters (Å, º)

C1—H1	0.990 (15)	C5—N1	1.3383 (16)
C1—C2	1.3809 (18)	C6—C6^i	1.537 (2)
C1—N1	1.3352 (17)	C6—H6A	0.969 (17)
C2—H2	0.989 (15)	C6—H6B	0.986 (18)
C2—C3	1.3919 (18)	C7—C8	1.4896 (18)
C3—C4	1.3897 (18)	C7—O1	1.3081 (14)
C3—C6	1.5038 (17)	C7—O2	1.2185 (15)
C4—H4	0.986 (15)	C8—C8^ii	1.317 (3)
C4—C5	1.3796 (18)	C8—H8	0.919 (16)
C5—H5	0.972 (16)	O1—H1A	1.04 (2)
C2—C1—H1	121.5 (9)	C3—C6—C6^i	110.64 (13)
N1—C1—H1	115.8 (9)	C3—C6—H6A	111.0 (10)
N1—C1—C2	122.62 (11)	C3—C6—H6B	110.6 (10)
C1—C2—H2	119.9 (9)	C6^i—C6—H6A	107.5 (10)
C1—C2—C3	119.40 (11)	C6^i—C6—H6B	107.0 (10)
C3—C2—H2	120.7 (9)	H6A—C6—H6B	110.0 (14)
C2—C3—C6	120.92 (11)	C1—N1—C5	118.24 (11)
C4—C3—C2	117.68 (11)	O1—C7—C8	114.10 (11)
C4—C3—C6	121.34 (11)	O2—C7—C8	121.20 (11)
C3—C4—H4	122.1 (9)	O2—C7—O1	124.70 (11)
C5—C4—C3	119.36 (12)	C7—C8—H8	114.5 (10)
C5—C4—H4	118.5 (9)	C8^ii—C8—C7	123.86 (15)
C4—C5—H5	120.9 (9)	C8^ii—C8—H8	121.6 (10)
N1—C5—C4	122.70 (12)	C7—O1—H1A	109.3 (11)
N1—C5—H5	116.4 (9)
C1—C2—C3—C4	0.20 (19)	C4—C3—C6—C6^i	−91.90 (17)
C1—C2—C3—C6	−177.07 (11)	C4—C5—N1—C1	0.3 (2)
C2—C1—N1—C5	0.1 (2)	C6—C3—C4—C5	177.45 (11)
C2—C3—C4—C5	0.19 (19)	N1—C1—C2—C3	−0.4 (2)
C2—C3—C6—C6^i	85.27 (17)	O1—C7—C8—C8^ii	−2.9 (2)
C3—C4—C5—N1	−0.5 (2)	O2—C7—C8—C8^ii	177.10 (16)

Symmetry codes: (i) −x, −y, −z+1; (ii) −x+1/2, −y+5/2, −z+1/2.

1,2-bis(4-Pyridyl)ethane fumaric acid (etyfum_160k_b)

Crystal data

C12H12N2·C4H4O4	F(000) = 632
Mr = 300.31	Dx = 1.362 Mg m^−3
Monoclinic, I2/a	Cu Kα radiation, λ = 1.54184 Å
a = 16.6868 (6) Å	Cell parameters from 2266 reflections
b = 4.7394 (1) Å	θ = 4.3–71.4°
c = 19.6945 (7) Å	µ = 0.82 mm^−1
β = 109.936 (4)°	T = 160 K
V = 1464.21 (9) Å^3	Block, colourless
Z = 4	0.41 × 0.29 × 0.16 mm

Data collection

New Xcalibur, EosS2 diffractometer	1397 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Cu) X-ray Source	1271 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
Detector resolution: 8.0294 pixels mm^-1	θmax = 71.5°, θmin = 4.8°
ω scans	h = −20→19
Absorption correction: gaussian CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −5→3
Tmin = 0.787, Tmax = 0.900	l = −23→24
4147 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	All H-atom parameters refined
wR(F^2) = 0.117	w = 1/[σ^2(Fo^2) + (0.0767P)^2 + 0.3236P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
1397 reflections	Δρmax = 0.20 e Å^−3
132 parameters	Δρmin = −0.22 e Å^−3
1 restraint

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
C1	0.15905 (8)	0.4038 (3)	0.41424 (7)	0.0284 (3)
H1	0.2198 (10)	0.462 (3)	0.4310 (8)	0.031 (4)*
C2	0.13103 (8)	0.2053 (3)	0.45230 (7)	0.0287 (3)
H2	0.1719 (10)	0.117 (3)	0.4957 (8)	0.032 (4)*
C3	0.04543 (8)	0.1288 (3)	0.42832 (6)	0.0242 (3)
C4	−0.00837 (8)	0.2577 (3)	0.36606 (7)	0.0269 (3)
H4	−0.0696 (9)	0.215 (4)	0.3458 (7)	0.032 (4)*
C5	0.02473 (8)	0.4529 (3)	0.33079 (7)	0.0266 (3)
H5	−0.0125 (9)	0.547 (3)	0.2877 (8)	0.028 (4)*
C6	0.01170 (9)	−0.0764 (3)	0.47029 (7)	0.0279 (3)
H6A	−0.0384 (11)	−0.170 (3)	0.4396 (9)	0.032 (4)*
H6B	0.0553 (11)	−0.220 (4)	0.4940 (9)	0.042 (4)*
N1	0.10711 (6)	0.5264 (2)	0.35434 (5)	0.0254 (3)
C7	0.24193 (7)	0.9766 (3)	0.32042 (6)	0.0249 (3)
C8	0.27257 (8)	1.2001 (3)	0.28213 (7)	0.0267 (3)
H8	0.3276 (10)	1.268 (4)	0.3064 (8)	0.037 (4)*
O1	0.16370 (5)	0.8939 (2)	0.28625 (5)	0.0305 (3)
H1A	0.1458 (13)	0.750 (4)	0.3174 (10)	0.072 (6)*
O2	0.28751 (6)	0.8847 (2)	0.37845 (5)	0.0332 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0231 (6)	0.0327 (7)	0.0303 (6)	−0.0025 (5)	0.0102 (5)	0.0023 (5)
C2	0.0278 (6)	0.0314 (7)	0.0266 (6)	0.0007 (5)	0.0090 (5)	0.0045 (5)
C3	0.0296 (6)	0.0218 (6)	0.0251 (6)	−0.0006 (5)	0.0145 (5)	−0.0022 (5)
C4	0.0248 (6)	0.0281 (7)	0.0288 (6)	−0.0031 (5)	0.0102 (5)	−0.0007 (5)
C5	0.0267 (6)	0.0283 (6)	0.0244 (6)	−0.0015 (5)	0.0083 (5)	0.0019 (5)
C6	0.0335 (7)	0.0242 (6)	0.0298 (7)	−0.0030 (5)	0.0159 (6)	0.0001 (5)
N1	0.0272 (6)	0.0258 (6)	0.0255 (5)	−0.0021 (4)	0.0119 (4)	0.0019 (4)
C7	0.0246 (6)	0.0256 (6)	0.0255 (6)	−0.0006 (5)	0.0099 (5)	−0.0004 (5)
C8	0.0229 (6)	0.0275 (7)	0.0304 (6)	−0.0042 (5)	0.0100 (5)	0.0003 (5)
O1	0.0255 (5)	0.0345 (6)	0.0295 (5)	−0.0069 (4)	0.0066 (4)	0.0081 (4)
O2	0.0287 (5)	0.0394 (6)	0.0286 (5)	−0.0033 (4)	0.0062 (4)	0.0082 (4)

Geometric parameters (Å, º)

C1—H1	0.992 (15)	C5—N1	1.3384 (16)
C1—C2	1.3801 (18)	C6—C6^i	1.535 (2)
C1—N1	1.3353 (16)	C6—H6A	0.956 (17)
C2—H2	0.987 (15)	C6—H6B	0.990 (18)
C2—C3	1.3910 (17)	C7—C8	1.4884 (18)
C3—C4	1.3900 (18)	C7—O1	1.3082 (14)
C3—C6	1.5041 (17)	C7—O2	1.2172 (15)
C4—H4	0.984 (15)	C8—C8^ii	1.320 (3)
C4—C5	1.3802 (18)	C8—H8	0.935 (16)
C5—H5	0.972 (15)	O1—H1A	1.028 (16)
C2—C1—H1	120.4 (9)	C3—C6—C6^i	110.74 (13)
N1—C1—H1	117.0 (9)	C3—C6—H6A	111.1 (10)
N1—C1—C2	122.57 (11)	C3—C6—H6B	110.5 (10)
C1—C2—H2	119.8 (9)	C6^i—C6—H6A	107.8 (10)
C1—C2—C3	119.50 (11)	C6^i—C6—H6B	107.6 (10)
C3—C2—H2	120.7 (9)	H6A—C6—H6B	108.9 (13)
C2—C3—C6	121.03 (11)	C1—N1—C5	118.26 (11)
C4—C3—C2	117.67 (11)	O1—C7—C8	114.05 (10)
C4—C3—C6	121.25 (12)	O2—C7—C8	121.18 (11)
C3—C4—H4	122.4 (9)	O2—C7—O1	124.77 (11)
C5—C4—C3	119.32 (12)	C7—C8—H8	115.6 (10)
C5—C4—H4	118.3 (9)	C8^ii—C8—C7	123.94 (15)
C4—C5—H5	120.0 (9)	C8^ii—C8—H8	120.5 (10)
N1—C5—C4	122.69 (12)	C7—O1—H1A	109.5 (11)
N1—C5—H5	117.3 (9)
C1—C2—C3—C4	0.21 (19)	C4—C3—C6—C6^i	−91.85 (17)
C1—C2—C3—C6	−177.04 (12)	C4—C5—N1—C1	0.4 (2)
C2—C1—N1—C5	0.1 (2)	C6—C3—C4—C5	177.48 (11)
C2—C3—C4—C5	0.24 (18)	N1—C1—C2—C3	−0.4 (2)
C2—C3—C6—C6^i	85.30 (17)	O1—C7—C8—C8^ii	−3.0 (2)
C3—C4—C5—N1	−0.5 (2)	O2—C7—C8—C8^ii	177.19 (16)

Symmetry codes: (i) −x, −y, −z+1; (ii) −x+1/2, −y+5/2, −z+1/2.

1,2-bis(4-Pyridyl)ethane fumaric acid (etyfum_165k_b)

Crystal data

C12H12N2·C4H4O4	F(000) = 632
Mr = 300.31	Dx = 1.362 Mg m^−3
Monoclinic, I2/a	Cu Kα radiation, λ = 1.54184 Å
a = 16.6819 (6) Å	Cell parameters from 2250 reflections
b = 4.7422 (2) Å	θ = 4.3–71.3°
c = 19.6945 (8) Å	µ = 0.82 mm^−1
β = 109.915 (4)°	T = 165 K
V = 1464.84 (11) Å^3	Block, colourless
Z = 4	0.41 × 0.29 × 0.16 mm

Data collection

New Xcalibur, EosS2 diffractometer	1399 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Cu) X-ray Source	1263 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
Detector resolution: 8.0294 pixels mm^-1	θmax = 71.6°, θmin = 4.8°
ω scans	h = −20→19
Absorption correction: gaussian CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −5→3
Tmin = 0.787, Tmax = 0.900	l = −23→24
4144 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.040	All H-atom parameters refined
wR(F^2) = 0.116	w = 1/[σ^2(Fo^2) + (0.0769P)^2 + 0.3081P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
1399 reflections	Δρmax = 0.18 e Å^−3
132 parameters	Δρmin = −0.24 e Å^−3
0 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
C1	0.15893 (8)	0.4041 (3)	0.41434 (7)	0.0286 (3)
H1	0.2189 (9)	0.465 (3)	0.4303 (8)	0.029 (4)*
C2	0.13091 (8)	0.2059 (3)	0.45237 (7)	0.0287 (3)
H2	0.1722 (10)	0.120 (3)	0.4953 (8)	0.033 (4)*
C3	0.04537 (8)	0.1290 (3)	0.42829 (6)	0.0248 (3)
C4	−0.00834 (8)	0.2577 (3)	0.36604 (7)	0.0271 (3)
H4	−0.0696 (9)	0.217 (4)	0.3458 (7)	0.032 (4)*
C5	0.02475 (8)	0.4527 (3)	0.33078 (7)	0.0272 (3)
H5	−0.0128 (10)	0.545 (3)	0.2873 (8)	0.030 (4)*
C6	0.01169 (9)	−0.0763 (3)	0.47026 (7)	0.0281 (3)
H6A	−0.0402 (11)	−0.169 (3)	0.4380 (9)	0.036 (4)*
H6B	0.0553 (10)	−0.218 (4)	0.4934 (8)	0.039 (4)*
N1	0.10706 (7)	0.5265 (2)	0.35431 (5)	0.0258 (3)
C7	0.24177 (7)	0.9770 (3)	0.32042 (6)	0.0251 (3)
C8	0.27247 (8)	1.2001 (3)	0.28206 (7)	0.0270 (3)
H8	0.3274 (10)	1.268 (4)	0.3076 (8)	0.033 (4)*
O1	0.16369 (5)	0.8942 (2)	0.28624 (5)	0.0309 (3)
H1A	0.1453 (13)	0.746 (5)	0.3176 (11)	0.069 (6)*
O2	0.28746 (6)	0.8849 (2)	0.37845 (5)	0.0340 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0233 (6)	0.0326 (7)	0.0304 (6)	−0.0022 (5)	0.0098 (5)	0.0023 (5)
C2	0.0280 (6)	0.0315 (7)	0.0267 (6)	0.0010 (5)	0.0092 (5)	0.0046 (5)
C3	0.0304 (6)	0.0225 (6)	0.0257 (6)	−0.0009 (5)	0.0150 (5)	−0.0018 (5)
C4	0.0247 (6)	0.0287 (7)	0.0293 (6)	−0.0038 (5)	0.0108 (5)	−0.0009 (5)
C5	0.0281 (6)	0.0283 (6)	0.0246 (6)	−0.0016 (5)	0.0083 (5)	0.0021 (5)
C6	0.0347 (7)	0.0241 (6)	0.0297 (7)	−0.0030 (5)	0.0163 (6)	0.0007 (5)
N1	0.0277 (5)	0.0264 (6)	0.0253 (5)	−0.0019 (4)	0.0118 (4)	0.0023 (4)
C7	0.0246 (6)	0.0262 (6)	0.0255 (6)	−0.0005 (5)	0.0096 (5)	−0.0003 (5)
C8	0.0235 (6)	0.0278 (7)	0.0299 (6)	−0.0041 (5)	0.0093 (5)	0.0006 (5)
O1	0.0259 (5)	0.0350 (6)	0.0298 (5)	−0.0073 (4)	0.0067 (4)	0.0085 (4)
O2	0.0295 (5)	0.0401 (6)	0.0292 (5)	−0.0034 (4)	0.0058 (4)	0.0084 (4)

Geometric parameters (Å, º)

C1—H1	0.986 (15)	C5—N1	1.3375 (16)
C1—C2	1.3790 (18)	C6—C6^i	1.536 (2)
C1—N1	1.3366 (16)	C6—H6A	0.986 (17)
C2—H2	0.980 (16)	C6—H6B	0.981 (17)
C2—C3	1.3903 (18)	C7—C8	1.4886 (18)
C3—C4	1.3890 (18)	C7—O1	1.3064 (14)
C3—C6	1.5045 (17)	C7—O2	1.2182 (15)
C4—H4	0.981 (15)	C8—C8^ii	1.318 (3)
C4—C5	1.3798 (18)	C8—H8	0.939 (15)
C5—H5	0.976 (15)	O1—H1A	1.05 (2)
C2—C1—H1	121.5 (9)	C3—C6—C6^i	110.69 (13)
N1—C1—H1	115.8 (9)	C3—C6—H6A	110.3 (10)
N1—C1—C2	122.64 (11)	C3—C6—H6B	110.1 (10)
C1—C2—H2	119.0 (9)	C6^i—C6—H6A	107.8 (10)
C1—C2—C3	119.46 (11)	C6^i—C6—H6B	108.0 (9)
C3—C2—H2	121.5 (9)	H6A—C6—H6B	109.9 (13)
C2—C3—C6	120.94 (11)	C1—N1—C5	118.14 (11)
C4—C3—C2	117.68 (11)	O1—C7—C8	114.02 (11)
C4—C3—C6	121.32 (12)	O2—C7—C8	121.14 (11)
C3—C4—H4	122.8 (9)	O2—C7—O1	124.83 (11)
C5—C4—C3	119.35 (12)	C7—C8—H8	114.5 (9)
C5—C4—H4	117.8 (9)	C8^ii—C8—C7	124.06 (15)
C4—C5—H5	119.7 (9)	C8^ii—C8—H8	121.4 (10)
N1—C5—C4	122.72 (12)	C7—O1—H1A	109.8 (11)
N1—C5—H5	117.6 (9)
C1—C2—C3—C4	0.12 (19)	C4—C3—C6—C6^i	−91.97 (17)
C1—C2—C3—C6	−177.12 (12)	C4—C5—N1—C1	0.3 (2)
C2—C1—N1—C5	0.2 (2)	C6—C3—C4—C5	177.55 (11)
C2—C3—C4—C5	0.33 (19)	N1—C1—C2—C3	−0.4 (2)
C2—C3—C6—C6^i	85.17 (17)	O1—C7—C8—C8^ii	−2.8 (2)
C3—C4—C5—N1	−0.5 (2)	O2—C7—C8—C8^ii	177.08 (16)

Symmetry codes: (i) −x, −y, −z+1; (ii) −x+1/2, −y+5/2, −z+1/2.

1,2-bis(4-Pyridyl)ethane fumaric acid (etyfum_170k_b)

Crystal data

C12H12N2·C4H4O4	F(000) = 632
Mr = 300.31	Dx = 1.360 Mg m^−3
Monoclinic, I2/a	Cu Kα radiation, λ = 1.54184 Å
a = 16.6847 (7) Å	Cell parameters from 2260 reflections
b = 4.7475 (2) Å	θ = 4.3–71.3°
c = 19.6847 (9) Å	µ = 0.82 mm^−1
β = 109.844 (5)°	T = 170 K
V = 1466.65 (12) Å^3	Block, colourless
Z = 4	0.41 × 0.29 × 0.16 mm

Data collection

New Xcalibur, EosS2 diffractometer	1403 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Cu) X-ray Source	1260 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
Detector resolution: 8.0294 pixels mm^-1	θmax = 71.4°, θmin = 4.8°
ω scans	h = −20→19
Absorption correction: gaussian CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −5→3
Tmin = 0.787, Tmax = 0.900	l = −23→24
4135 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	All H-atom parameters refined
wR(F^2) = 0.120	w = 1/[σ^2(Fo^2) + (0.0787P)^2 + 0.2755P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
1403 reflections	Δρmax = 0.18 e Å^−3
132 parameters	Δρmin = −0.22 e Å^−3
1 restraint

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
C1	0.15896 (8)	0.4045 (3)	0.41436 (7)	0.0294 (3)
H1	0.2187 (10)	0.465 (3)	0.4305 (8)	0.030 (4)*
C2	0.13094 (8)	0.2065 (3)	0.45236 (7)	0.0294 (3)
H2	0.1717 (10)	0.120 (3)	0.4963 (8)	0.031 (4)*
C3	0.04540 (8)	0.1294 (3)	0.42830 (6)	0.0251 (3)
C4	−0.00834 (8)	0.2573 (3)	0.36604 (7)	0.0278 (3)
H4	−0.0705 (10)	0.214 (4)	0.3457 (8)	0.035 (4)*
C5	0.02481 (8)	0.4529 (3)	0.33085 (7)	0.0279 (3)
H5	−0.0136 (10)	0.544 (3)	0.2873 (8)	0.033 (4)*
C6	0.01177 (9)	−0.0757 (3)	0.47028 (7)	0.0287 (3)
H6A	−0.0391 (11)	−0.168 (3)	0.4382 (9)	0.035 (4)*
H6B	0.0557 (11)	−0.219 (4)	0.4937 (9)	0.041 (4)*
N1	0.10706 (7)	0.5264 (2)	0.35429 (6)	0.0267 (3)
C7	0.24186 (8)	0.9770 (3)	0.32042 (6)	0.0258 (3)
C8	0.27243 (8)	1.2002 (3)	0.28203 (7)	0.0278 (3)
H8	0.3275 (10)	1.269 (4)	0.3068 (8)	0.040 (4)*
O1	0.16374 (6)	0.8939 (2)	0.28628 (5)	0.0319 (3)
H1A	0.1459 (13)	0.750 (4)	0.3175 (10)	0.077 (7)*
O2	0.28740 (6)	0.8853 (2)	0.37846 (5)	0.0348 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0240 (6)	0.0338 (7)	0.0307 (6)	−0.0027 (5)	0.0099 (5)	0.0030 (5)
C2	0.0281 (6)	0.0328 (7)	0.0271 (6)	0.0005 (5)	0.0089 (5)	0.0047 (5)
C3	0.0311 (6)	0.0232 (6)	0.0249 (6)	−0.0020 (5)	0.0145 (5)	−0.0021 (5)
C4	0.0259 (6)	0.0296 (7)	0.0292 (7)	−0.0035 (5)	0.0111 (5)	−0.0009 (5)
C5	0.0284 (6)	0.0294 (7)	0.0253 (6)	−0.0018 (5)	0.0084 (5)	0.0025 (5)
C6	0.0357 (7)	0.0248 (7)	0.0300 (7)	−0.0031 (5)	0.0170 (6)	0.0006 (5)
N1	0.0288 (6)	0.0272 (6)	0.0266 (5)	−0.0025 (4)	0.0126 (4)	0.0016 (4)
C7	0.0257 (6)	0.0272 (7)	0.0256 (6)	−0.0013 (5)	0.0101 (5)	−0.0005 (5)
C8	0.0239 (6)	0.0289 (7)	0.0311 (7)	−0.0043 (5)	0.0099 (5)	0.0010 (5)
O1	0.0273 (5)	0.0358 (6)	0.0302 (5)	−0.0072 (4)	0.0066 (4)	0.0088 (4)
O2	0.0303 (5)	0.0414 (6)	0.0295 (5)	−0.0036 (4)	0.0058 (4)	0.0089 (4)

Geometric parameters (Å, º)

C1—H1	0.981 (15)	C5—N1	1.3373 (16)
C1—C2	1.3784 (19)	C6—C6^i	1.534 (3)
C1—N1	1.3370 (17)	C6—H6A	0.974 (17)
C2—H2	0.989 (15)	C6—H6B	0.992 (18)
C2—C3	1.3915 (18)	C7—C8	1.4887 (18)
C3—C4	1.3888 (18)	C7—O1	1.3082 (15)
C3—C6	1.5036 (17)	C7—O2	1.2179 (15)
C4—H4	0.999 (15)	C8—C8^ii	1.316 (3)
C4—C5	1.3812 (18)	C8—H8	0.940 (17)
C5—H5	0.980 (16)	O1—H1A	1.028 (16)
C2—C1—H1	121.2 (9)	C3—C6—C6^i	110.83 (13)
N1—C1—H1	116.3 (9)	C3—C6—H6A	109.9 (10)
N1—C1—C2	122.55 (12)	C3—C6—H6B	110.2 (10)
C1—C2—H2	119.8 (9)	C6^i—C6—H6A	108.3 (10)
C1—C2—C3	119.49 (12)	C6^i—C6—H6B	107.9 (10)
C3—C2—H2	120.7 (9)	H6A—C6—H6B	109.6 (13)
C2—C3—C6	120.94 (12)	C1—N1—C5	118.22 (11)
C4—C3—C2	117.76 (11)	O1—C7—C8	114.03 (11)
C4—C3—C6	121.24 (12)	O2—C7—C8	121.25 (11)
C3—C4—H4	122.3 (9)	O2—C7—O1	124.72 (12)
C5—C4—C3	119.21 (12)	C7—C8—H8	115.2 (10)
C5—C4—H4	118.5 (9)	C8^ii—C8—C7	124.09 (15)
C4—C5—H5	118.8 (9)	C8^ii—C8—H8	120.7 (10)
N1—C5—C4	122.77 (12)	C7—O1—H1A	109.5 (12)
N1—C5—H5	118.4 (9)
C1—C2—C3—C4	0.22 (19)	C4—C3—C6—C6^i	−92.02 (17)
C1—C2—C3—C6	−177.10 (12)	C4—C5—N1—C1	0.0 (2)
C2—C1—N1—C5	0.3 (2)	C6—C3—C4—C5	177.43 (11)
C2—C3—C4—C5	0.12 (19)	N1—C1—C2—C3	−0.5 (2)
C2—C3—C6—C6^i	85.21 (18)	O1—C7—C8—C8^ii	−2.9 (2)
C3—C4—C5—N1	−0.2 (2)	O2—C7—C8—C8^ii	177.15 (17)

Symmetry codes: (i) −x, −y, −z+1; (ii) −x+1/2, −y+5/2, −z+1/2.

1,2-bis(4-Pyridyl)ethane fumaric acid (etyfum_175k_b)

Crystal data

C12H12N2·C4H4O4	F(000) = 632
Mr = 300.31	Dx = 1.359 Mg m^−3
Monoclinic, I2/a	Cu Kα radiation, λ = 1.54184 Å
a = 16.6837 (7) Å	Cell parameters from 2265 reflections
b = 4.7500 (2) Å	θ = 4.3–71.3°
c = 19.6845 (8) Å	µ = 0.82 mm^−1
β = 109.814 (5)°	T = 175 K
V = 1467.60 (11) Å^3	Block, colourless
Z = 4	0.41 × 0.29 × 0.16 mm

Data collection

New Xcalibur, EosS2 diffractometer	1406 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Cu) X-ray Source	1267 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
Detector resolution: 8.0294 pixels mm^-1	θmax = 71.5°, θmin = 4.8°
ω scans	h = −20→19
Absorption correction: gaussian CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −5→3
Tmin = 0.787, Tmax = 0.900	l = −23→24
4152 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	All H-atom parameters refined
wR(F^2) = 0.119	w = 1/[σ^2(Fo^2) + (0.0778P)^2 + 0.2792P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
1406 reflections	Δρmax = 0.19 e Å^−3
132 parameters	Δρmin = −0.23 e Å^−3
0 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
C1	0.15881 (8)	0.4051 (3)	0.41431 (7)	0.0297 (3)
H1	0.2193 (9)	0.464 (3)	0.4304 (8)	0.029 (4)*
C2	0.13099 (8)	0.2068 (3)	0.45241 (7)	0.0299 (3)
H2	0.1719 (10)	0.120 (3)	0.4958 (8)	0.036 (4)*
C3	0.04542 (8)	0.1298 (3)	0.42833 (6)	0.0255 (3)
C4	−0.00821 (8)	0.2575 (3)	0.36612 (7)	0.0280 (3)
H4	−0.0694 (9)	0.214 (4)	0.3460 (7)	0.033 (4)*
C5	0.02472 (8)	0.4529 (3)	0.33084 (7)	0.0281 (3)
H5	−0.0117 (10)	0.544 (4)	0.2872 (9)	0.038 (4)*
C6	0.01174 (9)	−0.0756 (3)	0.47028 (7)	0.0291 (3)
H6A	−0.0392 (11)	−0.167 (3)	0.4388 (9)	0.033 (4)*
H6B	0.0560 (11)	−0.216 (4)	0.4931 (9)	0.043 (4)*
N1	0.10703 (7)	0.5268 (2)	0.35432 (5)	0.0270 (3)
C7	0.24182 (8)	0.9773 (3)	0.32037 (6)	0.0263 (3)
C8	0.27237 (8)	1.2002 (3)	0.28200 (7)	0.0282 (3)
H8	0.3257 (10)	1.268 (4)	0.3066 (8)	0.039 (4)*
O1	0.16374 (6)	0.8941 (2)	0.28627 (5)	0.0323 (3)
H1A	0.1466 (13)	0.747 (5)	0.3174 (11)	0.073 (6)*
O2	0.28733 (6)	0.8856 (2)	0.37839 (5)	0.0354 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0244 (6)	0.0346 (7)	0.0307 (6)	−0.0020 (5)	0.0100 (5)	0.0030 (5)
C2	0.0292 (6)	0.0328 (7)	0.0274 (6)	0.0004 (5)	0.0093 (5)	0.0045 (5)
C3	0.0311 (6)	0.0240 (6)	0.0251 (6)	−0.0012 (5)	0.0144 (5)	−0.0024 (5)
C4	0.0263 (6)	0.0296 (7)	0.0295 (6)	−0.0031 (5)	0.0114 (5)	−0.0003 (5)
C5	0.0291 (6)	0.0302 (7)	0.0247 (6)	−0.0016 (5)	0.0087 (5)	0.0026 (5)
C6	0.0361 (7)	0.0254 (7)	0.0304 (7)	−0.0032 (5)	0.0173 (6)	0.0009 (5)
N1	0.0280 (6)	0.0285 (6)	0.0267 (5)	−0.0030 (4)	0.0121 (4)	0.0019 (4)
C7	0.0263 (6)	0.0275 (6)	0.0257 (6)	−0.0009 (5)	0.0097 (5)	−0.0006 (5)
C8	0.0249 (6)	0.0288 (7)	0.0310 (6)	−0.0043 (5)	0.0095 (5)	0.0008 (5)
O1	0.0276 (5)	0.0363 (6)	0.0309 (5)	−0.0075 (4)	0.0070 (4)	0.0089 (4)
O2	0.0308 (5)	0.0423 (6)	0.0296 (5)	−0.0032 (4)	0.0058 (4)	0.0095 (4)

Geometric parameters (Å, º)

C1—H1	0.991 (15)	C5—N1	1.3388 (16)
C1—C2	1.3789 (19)	C6—C6^i	1.533 (2)
C1—N1	1.3357 (17)	C6—H6A	0.970 (17)
C2—H2	0.986 (16)	C6—H6B	0.982 (18)
C2—C3	1.3919 (18)	C7—C8	1.4874 (18)
C3—C4	1.3876 (18)	C7—O1	1.3080 (15)
C3—C6	1.5047 (17)	C7—O2	1.2177 (15)
C4—H4	0.983 (15)	C8—C8^ii	1.315 (3)
C4—C5	1.3798 (18)	C8—H8	0.916 (16)
C5—H5	0.969 (16)	O1—H1A	1.03 (2)
C2—C1—H1	121.0 (9)	C3—C6—C6^i	110.78 (13)
N1—C1—H1	116.3 (9)	C3—C6—H6A	110.6 (9)
N1—C1—C2	122.73 (12)	C3—C6—H6B	109.1 (10)
C1—C2—H2	119.7 (9)	C6^i—C6—H6A	107.6 (10)
C1—C2—C3	119.32 (12)	C6^i—C6—H6B	108.4 (10)
C3—C2—H2	121.0 (9)	H6A—C6—H6B	110.4 (13)
C2—C3—C6	120.93 (12)	C1—N1—C5	118.16 (11)
C4—C3—C2	117.77 (11)	O1—C7—C8	114.05 (11)
C4—C3—C6	121.25 (12)	O2—C7—C8	121.26 (11)
C3—C4—H4	122.3 (9)	O2—C7—O1	124.69 (12)
C5—C4—C3	119.37 (12)	C7—C8—H8	114.9 (10)
C5—C4—H4	118.3 (9)	C8^ii—C8—C7	124.15 (15)
C4—C5—H5	120.5 (10)	C8^ii—C8—H8	121.0 (10)
N1—C5—C4	122.65 (12)	C7—O1—H1A	109.2 (11)
N1—C5—H5	116.8 (10)
C1—C2—C3—C4	0.29 (19)	C4—C3—C6—C6^i	−92.12 (17)
C1—C2—C3—C6	−177.11 (12)	C4—C5—N1—C1	0.1 (2)
C2—C1—N1—C5	0.3 (2)	C6—C3—C4—C5	177.49 (11)
C2—C3—C4—C5	0.10 (19)	N1—C1—C2—C3	−0.5 (2)
C2—C3—C6—C6^i	85.19 (18)	O1—C7—C8—C8^ii	−2.9 (2)
C3—C4—C5—N1	−0.3 (2)	O2—C7—C8—C8^ii	177.16 (17)

Symmetry codes: (i) −x, −y, −z+1; (ii) −x+1/2, −y+5/2, −z+1/2.

1,2-bis(4-Pyridyl)ethane fumaric acid (etyfum_180k_b)

Crystal data

C12H12N2·C4H4O4	F(000) = 632
Mr = 300.31	Dx = 1.359 Mg m^−3
Monoclinic, I2/a	Cu Kα radiation, λ = 1.54184 Å
a = 16.6837 (6) Å	Cell parameters from 2245 reflections
b = 4.7513 (2) Å	θ = 4.3–71.3°
c = 19.6812 (8) Å	µ = 0.82 mm^−1
β = 109.784 (4)°	T = 180 K
V = 1468.03 (11) Å^3	Block, colourless
Z = 4	0.41 × 0.29 × 0.16 mm

Data collection

New Xcalibur, EosS2 diffractometer	1408 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Cu) X-ray Source	1279 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
Detector resolution: 8.0294 pixels mm^-1	θmax = 71.5°, θmin = 4.8°
ω scans	h = −20→19
Absorption correction: gaussian CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −5→3
Tmin = 0.786, Tmax = 0.900	l = −23→24
4151 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	All H-atom parameters refined
wR(F^2) = 0.118	w = 1/[σ^2(Fo^2) + (0.0771P)^2 + 0.3806P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
1408 reflections	Δρmax = 0.20 e Å^−3
132 parameters	Δρmin = −0.23 e Å^−3
0 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
C1	0.15874 (8)	0.4054 (3)	0.41436 (7)	0.0306 (3)
H1	0.2193 (10)	0.464 (3)	0.4307 (8)	0.033 (4)*
C2	0.13089 (8)	0.2072 (3)	0.45238 (7)	0.0306 (3)
H2	0.1714 (10)	0.123 (3)	0.4952 (8)	0.032 (4)*
C3	0.04541 (8)	0.1297 (3)	0.42839 (6)	0.0259 (3)
C4	−0.00821 (8)	0.2575 (3)	0.36614 (7)	0.0285 (3)
H4	−0.0697 (9)	0.216 (3)	0.3455 (7)	0.031 (4)*
C5	0.02488 (8)	0.4529 (3)	0.33088 (7)	0.0286 (3)
H5	−0.0120 (10)	0.545 (4)	0.2877 (8)	0.034 (4)*
C6	0.01184 (9)	−0.0753 (3)	0.47031 (7)	0.0294 (3)
H6A	−0.0394 (11)	−0.168 (3)	0.4385 (9)	0.038 (4)*
H6B	0.0553 (11)	−0.218 (4)	0.4937 (9)	0.047 (5)*
N1	0.10707 (7)	0.5270 (2)	0.35437 (6)	0.0273 (3)
C7	0.24177 (8)	0.9774 (3)	0.32038 (6)	0.0264 (3)
C8	0.27240 (8)	1.2003 (3)	0.28201 (7)	0.0285 (3)
H8	0.3264 (10)	1.269 (4)	0.3077 (8)	0.039 (4)*
O1	0.16374 (6)	0.8944 (2)	0.28628 (5)	0.0330 (3)
H1A	0.1458 (14)	0.744 (5)	0.3176 (11)	0.080 (7)*
O2	0.28727 (6)	0.8861 (2)	0.37837 (5)	0.0362 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0254 (6)	0.0345 (7)	0.0322 (7)	−0.0021 (5)	0.0103 (5)	0.0034 (5)
C2	0.0284 (6)	0.0344 (7)	0.0283 (6)	0.0010 (5)	0.0088 (5)	0.0054 (5)
C3	0.0316 (6)	0.0241 (6)	0.0261 (6)	−0.0014 (5)	0.0152 (5)	−0.0018 (5)
C4	0.0254 (6)	0.0310 (7)	0.0298 (6)	−0.0037 (5)	0.0104 (5)	−0.0007 (5)
C5	0.0287 (6)	0.0307 (7)	0.0258 (6)	−0.0015 (5)	0.0083 (5)	0.0027 (5)
C6	0.0361 (7)	0.0250 (6)	0.0314 (7)	−0.0033 (5)	0.0170 (6)	0.0008 (5)
N1	0.0288 (6)	0.0282 (6)	0.0272 (5)	−0.0027 (4)	0.0122 (4)	0.0021 (4)
C7	0.0259 (6)	0.0278 (6)	0.0260 (6)	−0.0009 (5)	0.0094 (5)	−0.0004 (5)
C8	0.0243 (6)	0.0297 (7)	0.0314 (6)	−0.0042 (5)	0.0092 (5)	0.0005 (5)
O1	0.0276 (5)	0.0372 (6)	0.0315 (5)	−0.0076 (4)	0.0064 (4)	0.0091 (4)
O2	0.0316 (5)	0.0431 (6)	0.0304 (5)	−0.0040 (4)	0.0059 (4)	0.0091 (4)

Geometric parameters (Å, º)

C1—H1	0.990 (15)	C5—N1	1.3374 (16)
C1—C2	1.3775 (19)	C6—C6^i	1.532 (2)
C1—N1	1.3348 (17)	C6—H6A	0.977 (17)
C2—H2	0.971 (15)	C6—H6B	0.985 (19)
C2—C3	1.3917 (17)	C7—C8	1.4881 (18)
C3—C4	1.3886 (18)	C7—O1	1.3073 (15)
C3—C6	1.5019 (17)	C7—O2	1.2168 (15)
C4—H4	0.987 (14)	C8—C8^ii	1.316 (3)
C4—C5	1.3813 (18)	C8—H8	0.931 (16)
C5—H5	0.968 (16)	O1—H1A	1.05 (2)
C2—C1—H1	120.6 (9)	C3—C6—C6^i	110.90 (13)
N1—C1—H1	116.6 (9)	C3—C6—H6A	110.3 (10)
N1—C1—C2	122.73 (12)	C3—C6—H6B	110.5 (10)
C1—C2—H2	119.4 (9)	C6^i—C6—H6A	107.7 (10)
C1—C2—C3	119.47 (12)	C6^i—C6—H6B	107.7 (10)
C3—C2—H2	121.1 (9)	H6A—C6—H6B	109.6 (14)
C2—C3—C6	121.01 (12)	C1—N1—C5	118.13 (11)
C4—C3—C2	117.63 (11)	O1—C7—C8	114.05 (11)
C4—C3—C6	121.30 (12)	O2—C7—C8	121.15 (11)
C3—C4—H4	123.0 (9)	O2—C7—O1	124.79 (12)
C5—C4—C3	119.31 (11)	C7—C8—H8	114.2 (10)
C5—C4—H4	117.7 (9)	C8^ii—C8—C7	124.05 (15)
C4—C5—H5	120.0 (10)	C8^ii—C8—H8	121.7 (10)
N1—C5—C4	122.73 (12)	C7—O1—H1A	109.6 (11)
N1—C5—H5	117.2 (10)
C1—C2—C3—C4	0.28 (19)	C4—C3—C6—C6^i	−92.02 (17)
C1—C2—C3—C6	−177.06 (12)	C4—C5—N1—C1	0.1 (2)
C2—C1—N1—C5	0.4 (2)	C6—C3—C4—C5	177.49 (11)
C2—C3—C4—C5	0.17 (19)	N1—C1—C2—C3	−0.6 (2)
C2—C3—C6—C6^i	85.22 (18)	O1—C7—C8—C8^ii	−2.9 (2)
C3—C4—C5—N1	−0.4 (2)	O2—C7—C8—C8^ii	177.21 (16)

Symmetry codes: (i) −x, −y, −z+1; (ii) −x+1/2, −y+5/2, −z+1/2.

1,2-bis(4-Pyridyl)ethane fumaric acid (etyfum_185k_b)

Crystal data

C12H12N2·C4H4O4	F(000) = 632
Mr = 300.31	Dx = 1.358 Mg m^−3
Monoclinic, I2/a	Cu Kα radiation, λ = 1.54184 Å
a = 16.6800 (7) Å	Cell parameters from 2247 reflections
b = 4.7547 (2) Å	θ = 4.3–71.3°
c = 19.6846 (8) Å	µ = 0.82 mm^−1
β = 109.773 (5)°	T = 185 K
V = 1469.11 (11) Å^3	Block, colourless
Z = 4	0.41 × 0.29 × 0.16 mm

Data collection

New Xcalibur, EosS2 diffractometer	1408 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Cu) X-ray Source	1260 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
Detector resolution: 8.0294 pixels mm^-1	θmax = 71.5°, θmin = 4.8°
ω scans	h = −20→19
Absorption correction: gaussian CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −5→3
Tmin = 0.787, Tmax = 0.900	l = −23→24
4157 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.042	All H-atom parameters refined
wR(F^2) = 0.121	w = 1/[σ^2(Fo^2) + (0.079P)^2 + 0.3217P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
1408 reflections	Δρmax = 0.18 e Å^−3
132 parameters	Δρmin = −0.24 e Å^−3
0 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
C1	0.15868 (8)	0.4060 (3)	0.41429 (7)	0.0315 (3)
H1	0.2190 (10)	0.464 (4)	0.4305 (8)	0.036 (4)*
C2	0.13079 (8)	0.2078 (3)	0.45238 (7)	0.0316 (3)
H2	0.1730 (10)	0.123 (3)	0.4966 (8)	0.034 (4)*
C3	0.04539 (8)	0.1298 (3)	0.42840 (7)	0.0269 (3)
C4	−0.00815 (8)	0.2575 (3)	0.36611 (7)	0.0299 (3)
H4	−0.0692 (10)	0.212 (4)	0.3455 (8)	0.037 (4)*
C5	0.02494 (8)	0.4526 (3)	0.33090 (7)	0.0297 (3)
H5	−0.0124 (10)	0.546 (3)	0.2881 (8)	0.033 (4)*
C6	0.01182 (9)	−0.0753 (3)	0.47025 (7)	0.0307 (3)
H6A	−0.0382 (11)	−0.168 (4)	0.4392 (9)	0.040 (4)*
H6B	0.0559 (11)	−0.217 (4)	0.4939 (9)	0.045 (5)*
N1	0.10699 (7)	0.5272 (2)	0.35442 (6)	0.0286 (3)
C7	0.24167 (8)	0.9776 (3)	0.32035 (6)	0.0275 (3)
C8	0.27239 (8)	1.2005 (3)	0.28204 (7)	0.0296 (3)
H8	0.3267 (10)	1.272 (4)	0.3074 (9)	0.041 (4)*
O1	0.16376 (6)	0.8946 (2)	0.28629 (5)	0.0341 (3)
H1A	0.1449 (14)	0.748 (5)	0.3182 (11)	0.079 (7)*
O2	0.28721 (6)	0.8862 (2)	0.37838 (5)	0.0375 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0258 (6)	0.0358 (7)	0.0335 (7)	−0.0024 (5)	0.0106 (5)	0.0034 (5)
C2	0.0308 (7)	0.0352 (7)	0.0287 (7)	0.0009 (6)	0.0099 (5)	0.0055 (5)
C3	0.0339 (7)	0.0247 (7)	0.0266 (6)	−0.0012 (5)	0.0163 (5)	−0.0019 (5)
C4	0.0273 (6)	0.0317 (7)	0.0314 (7)	−0.0041 (5)	0.0110 (5)	−0.0006 (5)
C5	0.0300 (7)	0.0318 (7)	0.0264 (6)	−0.0017 (5)	0.0085 (5)	0.0031 (5)
C6	0.0383 (7)	0.0262 (7)	0.0324 (7)	−0.0036 (6)	0.0181 (6)	0.0011 (5)
N1	0.0302 (6)	0.0296 (6)	0.0283 (6)	−0.0029 (5)	0.0130 (4)	0.0022 (4)
C7	0.0271 (6)	0.0290 (7)	0.0273 (6)	−0.0012 (5)	0.0101 (5)	−0.0002 (5)
C8	0.0260 (6)	0.0306 (7)	0.0325 (7)	−0.0047 (5)	0.0103 (5)	0.0006 (5)
O1	0.0289 (5)	0.0387 (6)	0.0320 (5)	−0.0083 (4)	0.0067 (4)	0.0094 (4)
O2	0.0328 (5)	0.0449 (6)	0.0311 (5)	−0.0039 (4)	0.0062 (4)	0.0097 (4)

Geometric parameters (Å, º)

C1—H1	0.986 (16)	C5—N1	1.3358 (16)
C1—C2	1.3793 (19)	C6—C6^i	1.534 (3)
C1—N1	1.3330 (17)	C6—H6A	0.959 (18)
C2—H2	1.001 (15)	C6—H6B	0.990 (19)
C2—C3	1.3908 (18)	C7—C8	1.4887 (18)
C3—C4	1.3889 (18)	C7—O1	1.3056 (15)
C3—C6	1.5018 (17)	C7—O2	1.2179 (15)
C4—H4	0.984 (15)	C8—C8^ii	1.316 (3)
C4—C5	1.3798 (19)	C8—H8	0.937 (17)
C5—H5	0.970 (16)	O1—H1A	1.05 (2)
C2—C1—H1	120.6 (10)	C3—C6—C6^i	110.81 (14)
N1—C1—H1	116.7 (10)	C3—C6—H6A	110.7 (10)
N1—C1—C2	122.66 (12)	C3—C6—H6B	110.2 (10)
C1—C2—H2	118.8 (9)	C6^i—C6—H6A	108.0 (11)
C1—C2—C3	119.52 (12)	C6^i—C6—H6B	107.5 (10)
C3—C2—H2	121.7 (9)	H6A—C6—H6B	109.5 (14)
C2—C3—C6	121.07 (12)	C1—N1—C5	118.17 (11)
C4—C3—C2	117.51 (12)	O1—C7—C8	114.11 (11)
C4—C3—C6	121.36 (12)	O2—C7—C8	121.11 (12)
C3—C4—H4	122.2 (10)	O2—C7—O1	124.78 (12)
C5—C4—C3	119.36 (12)	C7—C8—H8	115.1 (10)
C5—C4—H4	118.4 (10)	C8^ii—C8—C7	123.99 (15)
C4—C5—H5	119.8 (9)	C8^ii—C8—H8	120.9 (10)
N1—C5—C4	122.78 (12)	C7—O1—H1A	109.8 (11)
N1—C5—H5	117.4 (9)
C1—C2—C3—C4	0.2 (2)	C4—C3—C6—C6^i	−92.19 (18)
C1—C2—C3—C6	−177.18 (12)	C4—C5—N1—C1	0.3 (2)
C2—C1—N1—C5	0.1 (2)	C6—C3—C4—C5	177.60 (12)
C2—C3—C4—C5	0.22 (19)	N1—C1—C2—C3	−0.4 (2)
C2—C3—C6—C6^i	85.09 (18)	O1—C7—C8—C8^ii	−3.0 (2)
C3—C4—C5—N1	−0.5 (2)	O2—C7—C8—C8^ii	177.09 (17)

Symmetry codes: (i) −x, −y, −z+1; (ii) −x+1/2, −y+5/2, −z+1/2.

1,2-bis(4-Pyridyl)ethane fumaric acid (etyfum_190k_b)

Crystal data

C12H12N2·C4H4O4	F(000) = 632
Mr = 300.31	Dx = 1.357 Mg m^−3
Monoclinic, I2/a	Cu Kα radiation, λ = 1.54184 Å
a = 16.6841 (7) Å	Cell parameters from 2220 reflections
b = 4.7564 (2) Å	θ = 4.3–71.3°
c = 19.6818 (8) Å	µ = 0.82 mm^−1
β = 109.740 (5)°	T = 190 K
V = 1470.09 (11) Å^3	Block, colourless
Z = 4	0.41 × 0.29 × 0.16 mm

Data collection

New Xcalibur, EosS2 diffractometer	1407 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Cu) X-ray Source	1255 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
Detector resolution: 8.0294 pixels mm^-1	θmax = 71.5°, θmin = 4.8°
ω scans	h = −20→19
Absorption correction: gaussian CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −5→3
Tmin = 0.787, Tmax = 0.900	l = −23→24
4152 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	All H-atom parameters refined
wR(F^2) = 0.118	w = 1/[σ^2(Fo^2) + (0.0769P)^2 + 0.3563P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
1407 reflections	Δρmax = 0.18 e Å^−3
132 parameters	Δρmin = −0.21 e Å^−3
0 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
C1	0.15868 (8)	0.4062 (3)	0.41435 (7)	0.0317 (3)
H1	0.2186 (10)	0.465 (3)	0.4298 (8)	0.036 (4)*
C2	0.13081 (8)	0.2080 (3)	0.45245 (7)	0.0319 (3)
H2	0.1716 (10)	0.123 (3)	0.4955 (8)	0.032 (4)*
C3	0.04552 (8)	0.1304 (3)	0.42841 (6)	0.0271 (3)
C4	−0.00818 (8)	0.2574 (3)	0.36617 (7)	0.0296 (3)
H4	−0.0687 (10)	0.214 (4)	0.3461 (8)	0.036 (4)*
C5	0.02501 (8)	0.4527 (3)	0.33098 (7)	0.0302 (3)
H5	−0.0125 (10)	0.548 (3)	0.2882 (8)	0.033 (4)*
C6	0.01192 (9)	−0.0750 (3)	0.47028 (7)	0.0311 (3)
H6A	−0.0395 (11)	−0.166 (3)	0.4382 (9)	0.037 (4)*
H6B	0.0552 (11)	−0.214 (4)	0.4936 (9)	0.043 (4)*
N1	0.10696 (7)	0.5274 (2)	0.35440 (6)	0.0285 (3)
C7	0.24164 (8)	0.9776 (3)	0.32032 (6)	0.0277 (3)
C8	0.27239 (8)	1.2007 (3)	0.28202 (7)	0.0299 (3)
H8	0.3258 (11)	1.267 (4)	0.3066 (9)	0.044 (5)*
O1	0.16379 (6)	0.8944 (2)	0.28626 (5)	0.0345 (3)
H1A	0.1460 (13)	0.749 (5)	0.3180 (11)	0.075 (7)*
O2	0.28715 (6)	0.8864 (2)	0.37829 (5)	0.0381 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0255 (6)	0.0363 (8)	0.0335 (7)	−0.0028 (5)	0.0103 (5)	0.0038 (5)
C2	0.0306 (7)	0.0354 (7)	0.0294 (7)	0.0003 (6)	0.0097 (5)	0.0061 (5)
C3	0.0334 (7)	0.0248 (7)	0.0272 (6)	−0.0020 (5)	0.0156 (5)	−0.0024 (5)
C4	0.0267 (6)	0.0314 (7)	0.0314 (7)	−0.0043 (5)	0.0110 (5)	−0.0002 (5)
C5	0.0309 (7)	0.0321 (7)	0.0269 (6)	−0.0019 (6)	0.0090 (5)	0.0029 (5)
C6	0.0387 (7)	0.0267 (7)	0.0326 (7)	−0.0033 (6)	0.0185 (6)	0.0009 (5)
N1	0.0303 (6)	0.0288 (6)	0.0285 (6)	−0.0032 (4)	0.0126 (4)	0.0021 (4)
C7	0.0277 (6)	0.0286 (7)	0.0276 (6)	−0.0011 (5)	0.0105 (5)	0.0007 (5)
C8	0.0261 (6)	0.0309 (7)	0.0331 (7)	−0.0051 (5)	0.0104 (5)	0.0014 (5)
O1	0.0290 (5)	0.0392 (6)	0.0325 (5)	−0.0084 (4)	0.0066 (4)	0.0099 (4)
O2	0.0328 (5)	0.0456 (6)	0.0319 (5)	−0.0043 (4)	0.0057 (4)	0.0103 (4)

Geometric parameters (Å, º)

C1—H1	0.982 (16)	C5—N1	1.3351 (16)
C1—C2	1.3795 (19)	C6—C6^i	1.533 (3)
C1—N1	1.3347 (17)	C6—H6A	0.976 (17)
C2—H2	0.978 (15)	C6—H6B	0.973 (18)
C2—C3	1.3893 (18)	C7—C8	1.4897 (18)
C3—C4	1.3882 (18)	C7—O1	1.3058 (15)
C3—C6	1.5032 (17)	C7—O2	1.2170 (16)
C4—H4	0.974 (15)	C8—C8^ii	1.316 (3)
C4—C5	1.3815 (18)	C8—H8	0.915 (17)
C5—H5	0.976 (16)	O1—H1A	1.04 (2)
C2—C1—H1	121.5 (10)	C3—C6—C6^i	110.91 (14)
N1—C1—H1	115.8 (10)	C3—C6—H6A	110.0 (10)
N1—C1—C2	122.67 (12)	C3—C6—H6B	110.2 (10)
C1—C2—H2	119.3 (9)	C6^i—C6—H6A	107.5 (10)
C1—C2—C3	119.41 (12)	C6^i—C6—H6B	107.5 (10)
C3—C2—H2	121.3 (9)	H6A—C6—H6B	110.7 (14)
C2—C3—C6	120.98 (12)	C1—N1—C5	118.11 (11)
C4—C3—C2	117.80 (12)	O1—C7—C8	114.15 (11)
C4—C3—C6	121.16 (12)	O2—C7—C8	121.05 (12)
C3—C4—H4	122.4 (10)	O2—C7—O1	124.81 (12)
C5—C4—C3	119.12 (12)	C7—C8—H8	114.8 (11)
C5—C4—H4	118.4 (9)	C8^ii—C8—C7	123.87 (15)
C4—C5—H5	119.8 (9)	C8^ii—C8—H8	121.4 (11)
N1—C5—C4	122.89 (12)	C7—O1—H1A	109.2 (11)
N1—C5—H5	117.2 (9)
C1—C2—C3—C4	0.2 (2)	C4—C3—C6—C6^i	−92.13 (18)
C1—C2—C3—C6	−177.17 (12)	C4—C5—N1—C1	0.2 (2)
C2—C1—N1—C5	0.2 (2)	C6—C3—C4—C5	177.57 (12)
C2—C3—C4—C5	0.18 (19)	N1—C1—C2—C3	−0.4 (2)
C2—C3—C6—C6^i	85.18 (18)	O1—C7—C8—C8^ii	−3.0 (2)
C3—C4—C5—N1	−0.4 (2)	O2—C7—C8—C8^ii	177.05 (17)

Symmetry codes: (i) −x, −y, −z+1; (ii) −x+1/2, −y+5/2, −z+1/2.

1,2-bis(4-Pyridyl)ethane fumaric acid (etyfum_200k_b)

Crystal data

C12H12N2·C4H4O4	F(000) = 632
Mr = 300.31	Dx = 1.355 Mg m^−3
Monoclinic, I2/a	Cu Kα radiation, λ = 1.54184 Å
a = 16.6798 (5) Å	Cell parameters from 2183 reflections
b = 4.7618 (1) Å	θ = 4.3–71.1°
c = 19.6808 (7) Å	µ = 0.82 mm^−1
β = 109.657 (4)°	T = 200 K
V = 1472.07 (8) Å^3	Block, colourless
Z = 4	0.41 × 0.29 × 0.16 mm

Data collection

New Xcalibur, EosS2 diffractometer	1412 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Cu) X-ray Source	1264 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
Detector resolution: 8.0294 pixels mm^-1	θmax = 71.5°, θmin = 4.8°
ω scans	h = −20→19
Absorption correction: gaussian CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −5→3
Tmin = 0.788, Tmax = 0.900	l = −23→24
4148 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	All H-atom parameters refined
wR(F^2) = 0.117	w = 1/[σ^2(Fo^2) + (0.0765P)^2 + 0.3152P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
1412 reflections	Δρmax = 0.17 e Å^−3
132 parameters	Δρmin = −0.24 e Å^−3
0 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
C1	0.15863 (8)	0.4070 (3)	0.41435 (7)	0.0330 (3)
H1	0.2186 (10)	0.469 (3)	0.4302 (8)	0.034 (4)*
C2	0.13071 (8)	0.2093 (3)	0.45247 (7)	0.0332 (3)
H2	0.1720 (10)	0.121 (3)	0.4956 (8)	0.037 (4)*
C3	0.04550 (8)	0.1308 (3)	0.42842 (6)	0.0280 (3)
C4	−0.00800 (8)	0.2574 (3)	0.36621 (7)	0.0309 (3)
H4	−0.0689 (9)	0.214 (3)	0.3466 (7)	0.034 (4)*
C5	0.02504 (8)	0.4530 (3)	0.33100 (7)	0.0311 (3)
H5	−0.0127 (10)	0.544 (3)	0.2884 (8)	0.034 (4)*
C6	0.01197 (9)	−0.0745 (3)	0.47034 (7)	0.0320 (3)
H6A	−0.0384 (11)	−0.170 (3)	0.4387 (9)	0.040 (4)*
H6B	0.0554 (11)	−0.214 (4)	0.4939 (9)	0.045 (4)*
N1	0.10696 (7)	0.5276 (2)	0.35442 (6)	0.0298 (3)
C7	0.24169 (8)	0.9780 (3)	0.32037 (6)	0.0290 (3)
C8	0.27220 (8)	1.2005 (3)	0.28194 (7)	0.0311 (3)
H8	0.3260 (10)	1.269 (4)	0.3071 (8)	0.043 (4)*
O1	0.16376 (6)	0.8947 (2)	0.28628 (5)	0.0360 (3)
H1A	0.1457 (13)	0.748 (5)	0.3175 (11)	0.074 (6)*
O2	0.28700 (6)	0.8868 (2)	0.37827 (5)	0.0398 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0266 (6)	0.0389 (7)	0.0339 (7)	−0.0030 (5)	0.0107 (5)	0.0043 (5)
C2	0.0318 (6)	0.0371 (7)	0.0301 (6)	0.0005 (6)	0.0096 (5)	0.0062 (6)
C3	0.0351 (6)	0.0258 (6)	0.0278 (6)	−0.0024 (5)	0.0167 (5)	−0.0022 (5)
C4	0.0280 (6)	0.0333 (7)	0.0326 (7)	−0.0043 (5)	0.0117 (5)	−0.0002 (5)
C5	0.0323 (7)	0.0333 (7)	0.0272 (6)	−0.0012 (5)	0.0091 (5)	0.0037 (5)
C6	0.0400 (7)	0.0275 (7)	0.0332 (7)	−0.0037 (6)	0.0183 (6)	0.0009 (5)
N1	0.0318 (6)	0.0306 (6)	0.0294 (5)	−0.0029 (4)	0.0132 (4)	0.0026 (4)
C7	0.0288 (6)	0.0305 (7)	0.0282 (6)	−0.0009 (5)	0.0101 (5)	0.0006 (5)
C8	0.0273 (6)	0.0330 (7)	0.0333 (6)	−0.0052 (5)	0.0106 (5)	0.0014 (5)
O1	0.0302 (5)	0.0407 (6)	0.0343 (5)	−0.0089 (4)	0.0073 (4)	0.0102 (4)
O2	0.0350 (5)	0.0475 (6)	0.0330 (5)	−0.0043 (4)	0.0063 (4)	0.0108 (4)

Geometric parameters (Å, º)

C1—H1	0.988 (15)	C5—N1	1.3349 (16)
C1—C2	1.3790 (19)	C6—C6^i	1.530 (3)
C1—N1	1.3340 (17)	C6—H6A	0.974 (17)
C2—H2	0.989 (16)	C6—H6B	0.978 (18)
C2—C3	1.3896 (18)	C7—C8	1.4872 (18)
C3—C4	1.3870 (18)	C7—O1	1.3078 (15)
C3—C6	1.5032 (17)	C7—O2	1.2160 (15)
C4—H4	0.979 (14)	C8—C8^ii	1.313 (3)
C4—C5	1.3815 (18)	C8—H8	0.926 (16)
C5—H5	0.966 (15)	O1—H1A	1.04 (2)
C2—C1—H1	121.7 (9)	C3—C6—C6^i	110.97 (13)
N1—C1—H1	115.7 (9)	C3—C6—H6A	110.6 (10)
N1—C1—C2	122.61 (12)	C3—C6—H6B	110.5 (10)
C1—C2—H2	119.4 (9)	C6^i—C6—H6A	108.3 (10)
C1—C2—C3	119.49 (12)	C6^i—C6—H6B	107.2 (10)
C3—C2—H2	121.1 (9)	H6A—C6—H6B	109.1 (14)
C2—C3—C6	120.98 (12)	C1—N1—C5	118.20 (11)
C4—C3—C2	117.67 (11)	O1—C7—C8	113.96 (11)
C4—C3—C6	121.30 (12)	O2—C7—C8	121.32 (12)
C3—C4—H4	122.1 (9)	O2—C7—O1	124.73 (12)
C5—C4—C3	119.28 (12)	C7—C8—H8	114.6 (10)
C5—C4—H4	118.7 (9)	C8^ii—C8—C7	124.29 (15)
C4—C5—H5	119.1 (9)	C8^ii—C8—H8	121.1 (10)
N1—C5—C4	122.75 (12)	C7—O1—H1A	109.6 (11)
N1—C5—H5	118.1 (9)
C1—C2—C3—C4	0.05 (19)	C4—C3—C6—C6^i	−92.20 (18)
C1—C2—C3—C6	−177.28 (12)	C4—C5—N1—C1	0.1 (2)
C2—C1—N1—C5	0.2 (2)	C6—C3—C4—C5	177.51 (11)
C2—C3—C4—C5	0.18 (19)	N1—C1—C2—C3	−0.2 (2)
C2—C3—C6—C6^i	85.04 (18)	O1—C7—C8—C8^ii	−2.9 (2)
C3—C4—C5—N1	−0.2 (2)	O2—C7—C8—C8^ii	177.09 (17)

Symmetry codes: (i) −x, −y, −z+1; (ii) −x+1/2, −y+5/2, −z+1/2.

1,2-bis(4-Pyridyl)ethane fumaric acid (etyfum_200k)

Crystal data

C12H12N2·C4H4O4	F(000) = 632
Mr = 300.31	Dx = 1.353 Mg m^−3
Monoclinic, I2/a	Cu Kα radiation, λ = 1.54184 Å
a = 16.6840 (7) Å	Cell parameters from 1612 reflections
b = 4.7634 (2) Å	θ = 3.0–72.2°
c = 19.6972 (7) Å	µ = 0.82 mm^−1
β = 109.674 (4)°	T = 200 K
V = 1474.00 (11) Å^3	Plate, colourless
Z = 4	0.25 × 0.14 × 0.04 mm

Data collection

SuperNova, Single source at offset/far, Atlas diffractometer	1426 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source	1187 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.024
Detector resolution: 10.5384 pixels mm^-1	θmax = 72.5°, θmin = 4.8°
ω scans	h = −19→20
Absorption correction: gaussian CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −5→5
Tmin = 0.705, Tmax = 1.000	l = −23→21
2815 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.034	w = 1/[σ^2(Fo^2) + (0.0463P)^2 + 0.3901P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.093	(Δ/σ)max < 0.001
S = 1.05	Δρmax = 0.19 e Å^−3
1426 reflections	Δρmin = −0.15 e Å^−3
133 parameters	Extinction correction: SHELXL-2014/7 (Sheldrick 2014, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0013 (2)
Primary atom site location: dual

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
C1	0.15859 (8)	0.4073 (3)	0.41442 (7)	0.0332 (3)
H1	0.2187 (10)	0.470 (3)	0.4303 (8)	0.034 (4)*
C2	0.13053 (8)	0.2088 (3)	0.45239 (7)	0.0333 (3)
H2	0.1710 (10)	0.121 (4)	0.4959 (9)	0.044 (4)*
C3	0.04550 (8)	0.1304 (3)	0.42840 (7)	0.0279 (3)
C4	−0.00802 (8)	0.2572 (3)	0.36623 (7)	0.0311 (3)
H4	−0.0689 (9)	0.214 (3)	0.3464 (8)	0.036 (4)*
C5	0.02488 (8)	0.4529 (3)	0.33091 (7)	0.0311 (3)
H5	−0.0120 (10)	0.544 (3)	0.2871 (8)	0.040 (4)*
C6	0.01204 (9)	−0.0753 (3)	0.47039 (7)	0.0328 (3)
H6A	−0.0393 (11)	−0.172 (4)	0.4376 (9)	0.046 (5)*
H6B	0.0567 (10)	−0.215 (4)	0.4937 (9)	0.045 (5)*
N1	0.10697 (7)	0.5281 (2)	0.35440 (6)	0.0302 (3)
C7	0.24173 (8)	0.9781 (3)	0.32046 (7)	0.0292 (3)
C8	0.27219 (8)	1.2010 (3)	0.28179 (7)	0.0312 (3)
H8	0.3285 (11)	1.267 (4)	0.3064 (9)	0.047 (5)*
O1	0.16373 (6)	0.8949 (2)	0.28625 (5)	0.0359 (3)
H1A	0.1437 (13)	0.744 (5)	0.3171 (11)	0.081 (7)*
O2	0.28710 (6)	0.8865 (2)	0.37835 (5)	0.0404 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0249 (7)	0.0386 (8)	0.0356 (7)	−0.0033 (6)	0.0095 (5)	0.0041 (6)
C2	0.0304 (7)	0.0375 (8)	0.0307 (6)	−0.0001 (6)	0.0086 (5)	0.0065 (6)
C3	0.0328 (7)	0.0260 (7)	0.0294 (6)	−0.0022 (5)	0.0165 (5)	−0.0019 (5)
C4	0.0276 (7)	0.0332 (8)	0.0328 (7)	−0.0043 (5)	0.0106 (5)	−0.0001 (6)
C5	0.0304 (7)	0.0326 (7)	0.0294 (6)	−0.0026 (5)	0.0089 (5)	0.0033 (5)
C6	0.0391 (8)	0.0289 (8)	0.0356 (7)	−0.0035 (6)	0.0191 (6)	0.0012 (6)
N1	0.0291 (6)	0.0315 (6)	0.0320 (6)	−0.0034 (5)	0.0127 (4)	0.0022 (5)
C7	0.0273 (6)	0.0310 (7)	0.0297 (6)	−0.0013 (5)	0.0099 (5)	0.0013 (5)
C8	0.0265 (6)	0.0333 (8)	0.0337 (6)	−0.0052 (5)	0.0100 (5)	0.0016 (5)
O1	0.0282 (5)	0.0410 (6)	0.0351 (5)	−0.0091 (4)	0.0062 (4)	0.0101 (4)
O2	0.0342 (5)	0.0485 (7)	0.0339 (5)	−0.0050 (5)	0.0053 (4)	0.0109 (5)

Geometric parameters (Å, º)

C1—H1	0.991 (15)	C6—C6^i	1.533 (3)
C1—C2	1.381 (2)	C6—H6A	0.995 (18)
C1—N1	1.3360 (17)	C6—H6B	0.988 (18)
C2—H2	0.988 (17)	N1—H1A	1.51 (2)
C2—C3	1.3870 (18)	C7—C8	1.4924 (19)
C3—C4	1.3875 (18)	C7—O1	1.3091 (15)
C3—C6	1.5054 (18)	C7—O2	1.2174 (16)
C4—H4	0.979 (15)	C8—C8^ii	1.308 (3)
C4—C5	1.3826 (19)	C8—H8	0.953 (17)
C5—H5	0.978 (16)	O1—H1A	1.07 (2)
C5—N1	1.3384 (17)
C2—C1—H1	121.8 (9)	C3—C6—H6A	109.9 (10)
N1—C1—H1	115.6 (9)	C3—C6—H6B	109.4 (10)
N1—C1—C2	122.61 (12)	C6^i—C6—H6A	108.7 (10)
C1—C2—H2	120.2 (10)	C6^i—C6—H6B	108.1 (10)
C1—C2—C3	119.61 (12)	H6A—C6—H6B	110.0 (14)
C3—C2—H2	120.2 (10)	C1—N1—C5	118.06 (11)
C2—C3—C4	117.64 (12)	C1—N1—H1A	118.6 (8)
C2—C3—C6	120.93 (12)	C5—N1—H1A	123.4 (8)
C4—C3—C6	121.37 (12)	O1—C7—C8	113.75 (11)
C3—C4—H4	122.2 (9)	O2—C7—C8	121.45 (12)
C5—C4—C3	119.41 (12)	O2—C7—O1	124.80 (12)
C5—C4—H4	118.4 (9)	C7—C8—H8	114.9 (10)
C4—C5—H5	120.4 (9)	C8^ii—C8—C7	124.22 (16)
N1—C5—C4	122.68 (12)	C8^ii—C8—H8	120.9 (10)
N1—C5—H5	116.9 (9)	C7—O1—H1A	111.0 (11)
C3—C6—C6^i	110.75 (14)
C1—C2—C3—C4	0.1 (2)	C4—C3—C6—C6^i	−92.00 (18)
C1—C2—C3—C6	−177.14 (13)	C4—C5—N1—C1	0.1 (2)
C2—C1—N1—C5	0.3 (2)	C6—C3—C4—C5	177.52 (12)
C2—C3—C4—C5	0.3 (2)	N1—C1—C2—C3	−0.4 (2)
C2—C3—C6—C6^i	85.18 (19)	O1—C7—C8—C8^ii	−2.9 (3)
C3—C4—C5—N1	−0.4 (2)	O2—C7—C8—C8^ii	176.94 (18)

Symmetry codes: (i) −x, −y, −z+1; (ii) −x+1/2, −y+5/2, −z+1/2.

1,2-bis(4-Pyridyl)ethane fumaric acid (ETYFUM_250K)

Crystal data

C12H12N2·C4H4O4	F(000) = 632
Mr = 300.31	Dx = 1.344 Mg m^−3
Monoclinic, I2/a	Cu Kα radiation, λ = 1.54184 Å
a = 16.6906 (9) Å	Cell parameters from 1500 reflections
b = 4.7903 (2) Å	θ = 4.7–71.7°
c = 19.6824 (9) Å	µ = 0.81 mm^−1
β = 109.367 (5)°	T = 250 K
V = 1484.62 (13) Å^3	Plate, colourless
Z = 4	0.26 × 0.14 × 0.05 mm

Data collection

SuperNova, Single source at offset/far, Atlas diffractometer	1432 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source	1131 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.025
Detector resolution: 10.5384 pixels mm^-1	θmax = 72.1°, θmin = 4.8°
ω scans	h = −20→19
Absorption correction: gaussian CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −5→5
Tmin = 0.599, Tmax = 1.000	l = −21→23
2821 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.035	w = 1/[σ^2(Fo^2) + (0.0476P)^2 + 0.2145P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.099	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.15 e Å^−3
1432 reflections	Δρmin = −0.13 e Å^−3
133 parameters	Extinction correction: SHELXL-2014/7 (Sheldrick 2014, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0014 (2)
Primary atom site location: dual

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
C1	0.15817 (9)	0.4111 (4)	0.41454 (8)	0.0401 (4)
H1	0.2195 (10)	0.472 (4)	0.4317 (9)	0.042 (4)*
C2	0.13020 (9)	0.2131 (4)	0.45264 (8)	0.0400 (4)
H2	0.1711 (11)	0.128 (4)	0.4964 (10)	0.051 (5)*
C3	0.04563 (9)	0.1329 (3)	0.42853 (7)	0.0329 (3)
C4	−0.00744 (9)	0.2575 (3)	0.36650 (8)	0.0378 (4)
H4	−0.0672 (11)	0.214 (4)	0.3463 (9)	0.050 (5)*
C5	0.02510 (9)	0.4530 (3)	0.33104 (8)	0.0376 (4)
H5	−0.0123 (11)	0.546 (4)	0.2865 (9)	0.050 (5)*
C6	0.01241 (11)	−0.0733 (3)	0.47042 (8)	0.0393 (4)
H6A	−0.0390 (11)	−0.170 (4)	0.4374 (9)	0.049 (5)*
H6B	0.0564 (11)	−0.212 (4)	0.4946 (9)	0.055 (5)*
N1	0.10664 (7)	0.5296 (3)	0.35458 (6)	0.0358 (3)
C7	0.24153 (9)	0.9795 (3)	0.32030 (7)	0.0352 (3)
C8	0.27201 (9)	1.2015 (3)	0.28178 (8)	0.0369 (4)
H8	0.3274 (11)	1.265 (4)	0.3061 (9)	0.054 (5)*
O1	0.16389 (6)	0.8960 (2)	0.28633 (6)	0.0432 (3)
H1A	0.1454 (13)	0.754 (5)	0.3165 (12)	0.091 (8)*
O2	0.28637 (7)	0.8895 (3)	0.37803 (6)	0.0492 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0304 (7)	0.0460 (10)	0.0432 (8)	−0.0043 (7)	0.0113 (6)	0.0066 (7)
C2	0.0369 (8)	0.0443 (9)	0.0382 (7)	−0.0003 (7)	0.0116 (6)	0.0086 (7)
C3	0.0382 (8)	0.0313 (8)	0.0338 (7)	−0.0029 (6)	0.0181 (6)	−0.0014 (6)
C4	0.0321 (7)	0.0429 (9)	0.0387 (7)	−0.0067 (6)	0.0122 (6)	0.0000 (7)
C5	0.0366 (8)	0.0409 (9)	0.0343 (7)	−0.0034 (6)	0.0104 (6)	0.0042 (6)
C6	0.0482 (9)	0.0337 (9)	0.0418 (8)	−0.0060 (7)	0.0225 (7)	0.0009 (7)
N1	0.0352 (6)	0.0372 (7)	0.0373 (6)	−0.0046 (5)	0.0150 (5)	0.0037 (5)
C7	0.0322 (7)	0.0384 (8)	0.0357 (7)	−0.0020 (6)	0.0123 (6)	0.0021 (6)
C8	0.0306 (7)	0.0396 (9)	0.0402 (7)	−0.0072 (6)	0.0114 (6)	0.0033 (6)
O1	0.0345 (6)	0.0496 (7)	0.0416 (6)	−0.0116 (5)	0.0073 (4)	0.0127 (5)
O2	0.0410 (6)	0.0601 (8)	0.0403 (6)	−0.0064 (5)	0.0053 (5)	0.0142 (5)

Geometric parameters (Å, º)

C1—H1	1.009 (16)	C5—N1	1.3354 (18)
C1—C2	1.383 (2)	C6—C6^i	1.530 (3)
C1—N1	1.3348 (19)	C6—H6A	1.003 (18)
C2—H2	0.992 (18)	C6—H6B	0.99 (2)
C2—C3	1.386 (2)	C7—C8	1.490 (2)
C3—C4	1.384 (2)	C7—O1	1.3083 (17)
C3—C6	1.505 (2)	C7—O2	1.2136 (17)
C4—H4	0.967 (17)	C8—C8^ii	1.308 (3)
C4—C5	1.382 (2)	C8—H8	0.940 (18)
C5—H5	0.997 (17)	O1—H1A	1.02 (2)
C2—C1—H1	120.3 (9)	C3—C6—C6^i	110.93 (16)
N1—C1—H1	117.2 (10)	C3—C6—H6A	110.0 (10)
N1—C1—C2	122.47 (14)	C3—C6—H6B	110.9 (11)
C1—C2—H2	119.5 (10)	C6^i—C6—H6A	108.4 (10)
C1—C2—C3	119.54 (14)	C6^i—C6—H6B	106.7 (11)
C3—C2—H2	120.9 (10)	H6A—C6—H6B	109.8 (15)
C2—C3—C6	120.84 (14)	C1—N1—C5	118.26 (12)
C4—C3—C2	117.64 (13)	O1—C7—C8	113.93 (12)
C4—C3—C6	121.48 (13)	O2—C7—C8	121.42 (13)
C3—C4—H4	122.7 (11)	O2—C7—O1	124.65 (13)
C5—C4—C3	119.61 (13)	C7—C8—H8	114.6 (11)
C5—C4—H4	117.7 (11)	C8^ii—C8—C7	124.17 (17)
C4—C5—H5	120.7 (10)	C8^ii—C8—H8	121.2 (11)
N1—C5—C4	122.48 (13)	C7—O1—H1A	110.4 (12)
N1—C5—H5	116.8 (10)
C1—C2—C3—C4	−0.1 (2)	C4—C3—C6—C6^i	−92.2 (2)
C1—C2—C3—C6	−177.48 (14)	C4—C5—N1—C1	0.2 (2)
C2—C1—N1—C5	0.1 (2)	C6—C3—C4—C5	177.77 (14)
C2—C3—C4—C5	0.4 (2)	N1—C1—C2—C3	−0.2 (2)
C2—C3—C6—C6^i	85.1 (2)	O1—C7—C8—C8^ii	−3.1 (3)
C3—C4—C5—N1	−0.5 (2)	O2—C7—C8—C8^ii	177.1 (2)

Symmetry codes: (i) −x, −y, −z+1; (ii) −x+1/2, −y+5/2, −z+1/2.

1,2-bis(4-Pyridyl)ethane fumaric acid (etyfum_300k_b)

Crystal data

C12H12N2·C4H4O4	F(000) = 632
Mr = 300.31	Dx = 1.335 Mg m^−3
Monoclinic, I2/a	Cu Kα radiation, λ = 1.54184 Å
a = 16.6920 (4) Å	Cell parameters from 1867 reflections
b = 4.8145 (1) Å	θ = 4.2–71.3°
c = 19.6756 (5) Å	µ = 0.81 mm^−1
β = 109.059 (3)°	T = 300 K
V = 1494.53 (7) Å^3	Block, colourless
Z = 4	0.41 × 0.29 × 0.16 mm

Data collection

New Xcalibur, EosS2 diffractometer	1428 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Cu) X-ray Source	1219 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
Detector resolution: 8.0294 pixels mm^-1	θmax = 71.4°, θmin = 4.8°
ω scans	h = −19→20
Absorption correction: gaussian CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −5→3
Tmin = 0.791, Tmax = 0.901	l = −24→23
4197 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.043	All H-atom parameters refined
wR(F^2) = 0.128	w = 1/[σ^2(Fo^2) + (0.0786P)^2 + 0.1853P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
1428 reflections	Δρmax = 0.17 e Å^−3
132 parameters	Δρmin = −0.19 e Å^−3
0 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
C1	0.15749 (9)	0.4151 (3)	0.41473 (8)	0.0471 (4)
H1	0.2171 (10)	0.471 (4)	0.4319 (9)	0.049 (4)*
C2	0.12995 (9)	0.2177 (3)	0.45262 (8)	0.0471 (4)
H2	0.1719 (10)	0.140 (4)	0.4963 (8)	0.049 (4)*
C3	0.04581 (9)	0.1356 (3)	0.42886 (7)	0.0386 (4)
C4	−0.00703 (9)	0.2581 (3)	0.36669 (8)	0.0431 (4)
H4	−0.0675 (10)	0.211 (4)	0.3462 (8)	0.050 (4)*
C5	0.02554 (9)	0.4526 (3)	0.33146 (8)	0.0439 (4)
H5	−0.0122 (12)	0.537 (4)	0.2877 (10)	0.060 (5)*
C6	0.01246 (11)	−0.0710 (3)	0.47028 (8)	0.0454 (4)
H6A	−0.0383 (12)	−0.171 (4)	0.4382 (10)	0.057 (5)*
H6B	0.0563 (12)	−0.204 (4)	0.4935 (10)	0.067 (6)*
N1	0.10645 (7)	0.5310 (3)	0.35470 (6)	0.0414 (3)
C7	0.24108 (9)	0.9810 (3)	0.32007 (7)	0.0406 (4)
C8	0.27153 (9)	1.2013 (3)	0.28176 (8)	0.0434 (4)
H8	0.3258 (11)	1.269 (4)	0.3071 (9)	0.061 (5)*
O1	0.16399 (6)	0.8974 (2)	0.28640 (6)	0.0504 (3)
H1A	0.1481 (13)	0.758 (5)	0.3167 (11)	0.087 (7)*
O2	0.28561 (7)	0.8922 (3)	0.37772 (6)	0.0575 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0360 (7)	0.0556 (9)	0.0493 (8)	−0.0051 (6)	0.0136 (6)	0.0085 (7)
C2	0.0431 (7)	0.0547 (9)	0.0429 (8)	0.0001 (7)	0.0130 (6)	0.0130 (7)
C3	0.0473 (8)	0.0368 (7)	0.0381 (7)	−0.0028 (6)	0.0228 (6)	−0.0012 (5)
C4	0.0386 (7)	0.0468 (8)	0.0440 (7)	−0.0086 (6)	0.0139 (6)	0.0013 (6)
C5	0.0435 (8)	0.0493 (8)	0.0373 (7)	−0.0035 (6)	0.0112 (6)	0.0065 (6)
C6	0.0594 (9)	0.0377 (8)	0.0476 (8)	−0.0061 (7)	0.0291 (7)	0.0018 (6)
N1	0.0429 (7)	0.0435 (7)	0.0407 (6)	−0.0054 (5)	0.0178 (5)	0.0043 (5)
C7	0.0396 (7)	0.0439 (8)	0.0381 (7)	−0.0029 (6)	0.0125 (6)	0.0026 (6)
C8	0.0371 (7)	0.0463 (8)	0.0464 (8)	−0.0082 (6)	0.0134 (6)	0.0035 (6)
O1	0.0427 (6)	0.0572 (7)	0.0471 (6)	−0.0131 (5)	0.0089 (5)	0.0158 (5)
O2	0.0491 (6)	0.0698 (8)	0.0466 (6)	−0.0090 (5)	0.0061 (5)	0.0175 (5)

Geometric parameters (Å, º)

C1—H1	0.979 (16)	C5—N1	1.3312 (18)
C1—C2	1.376 (2)	C6—C6^i	1.525 (3)
C1—N1	1.3324 (19)	C6—H6A	1.00 (2)
C2—H2	0.988 (16)	C6—H6B	0.97 (2)
C2—C3	1.385 (2)	C7—C8	1.484 (2)
C3—C4	1.385 (2)	C7—O1	1.3039 (16)
C3—C6	1.5033 (19)	C7—O2	1.2130 (17)
C4—H4	0.984 (16)	C8—C8^ii	1.308 (3)
C4—C5	1.378 (2)	C8—H8	0.938 (18)
C5—H5	0.973 (18)	O1—H1A	0.99 (2)
C2—C1—H1	119.0 (10)	C3—C6—C6^i	111.15 (15)
N1—C1—H1	118.4 (10)	C3—C6—H6A	111.4 (11)
N1—C1—C2	122.64 (13)	C3—C6—H6B	109.7 (12)
C1—C2—H2	117.7 (10)	C6^i—C6—H6A	108.2 (11)
C1—C2—C3	119.71 (13)	C6^i—C6—H6B	106.7 (11)
C3—C2—H2	122.6 (10)	H6A—C6—H6B	109.5 (15)
C2—C3—C6	121.34 (13)	C5—N1—C1	117.98 (12)
C4—C3—C2	117.36 (13)	O1—C7—C8	114.05 (12)
C4—C3—C6	121.27 (13)	O2—C7—C8	121.34 (13)
C3—C4—H4	122.4 (10)	O2—C7—O1	124.61 (13)
C5—C4—C3	119.46 (13)	C7—C8—H8	114.2 (11)
C5—C4—H4	118.1 (10)	C8^ii—C8—C7	124.69 (17)
C4—C5—H5	118.7 (11)	C8^ii—C8—H8	121.1 (11)
N1—C5—C4	122.85 (13)	C7—O1—H1A	108.5 (12)
N1—C5—H5	118.4 (11)
C1—C2—C3—C4	0.4 (2)	C4—C3—C6—C6^i	−93.2 (2)
C1—C2—C3—C6	−177.57 (14)	C4—C5—N1—C1	−0.1 (2)
C2—C1—N1—C5	0.7 (2)	C6—C3—C4—C5	178.11 (13)
C2—C3—C4—C5	0.2 (2)	N1—C1—C2—C3	−0.8 (3)
C2—C3—C6—C6^i	84.7 (2)	O1—C7—C8—C8^ii	−3.2 (3)
C3—C4—C5—N1	−0.3 (2)	O2—C7—C8—C8^ii	177.0 (2)

Symmetry codes: (i) −x, −y, −z+1; (ii) −x+1/2, −y+5/2, −z+1/2.

1,2-bis(4-Pyridyl)ethane fumaric acid (etyfum_300k)

Crystal data

C12H12N2·C4H4O4	F(000) = 632
Mr = 300.31	Dx = 1.335 Mg m^−3
Monoclinic, I2/a	Cu Kα radiation, λ = 1.54184 Å
a = 16.6911 (10) Å	Cell parameters from 1379 reflections
b = 4.8164 (3) Å	θ = 3.1–72.4°
c = 19.6669 (10) Å	µ = 0.81 mm^−1
β = 109.032 (6)°	T = 300 K
V = 1494.62 (16) Å^3	Plate, colourless
Z = 4	0.23 × 0.14 × 0.04 mm

Data collection

SuperNova, Single source at offset/far, Atlas diffractometer	1440 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source	1119 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.024
Detector resolution: 10.5384 pixels mm^-1	θmax = 72.6°, θmin = 4.8°
ω scans	h = −20→19
Absorption correction: gaussian CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −5→5
Tmin = 0.718, Tmax = 1.000	l = −21→23
2839 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.037	w = 1/[σ^2(Fo^2) + (0.0544P)^2 + 0.4091P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.108	(Δ/σ)max < 0.001
S = 1.02	Δρmax = 0.12 e Å^−3
1440 reflections	Δρmin = −0.15 e Å^−3
133 parameters	Extinction correction: SHELXL-2014/7 (Sheldrick 2014, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0016 (3)
Primary atom site location: dual

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
C1	0.15740 (10)	0.4149 (4)	0.41466 (9)	0.0479 (4)
H1	0.2173 (12)	0.478 (4)	0.4312 (10)	0.061 (5)*
C2	0.12963 (10)	0.2174 (4)	0.45261 (9)	0.0476 (4)
H2	0.1707 (12)	0.136 (4)	0.4964 (10)	0.059 (5)*
C3	0.04574 (10)	0.1351 (3)	0.42878 (8)	0.0391 (4)
C4	−0.00688 (10)	0.2576 (4)	0.36668 (8)	0.0444 (4)
H4	−0.0669 (12)	0.216 (4)	0.3473 (10)	0.060 (5)*
C5	0.02545 (10)	0.4526 (4)	0.33139 (8)	0.0450 (4)
H5	−0.0118 (12)	0.538 (4)	0.2874 (10)	0.062 (5)*
C6	0.01267 (12)	−0.0712 (4)	0.47038 (9)	0.0465 (4)
H6A	−0.0388 (13)	−0.171 (4)	0.4372 (11)	0.066 (6)*
H6B	0.0572 (13)	−0.209 (5)	0.4948 (11)	0.072 (6)*
N1	0.10668 (8)	0.5310 (3)	0.35474 (7)	0.0424 (4)
C7	0.24122 (9)	0.9811 (4)	0.32014 (8)	0.0411 (4)
C8	0.27168 (10)	1.2013 (4)	0.28170 (8)	0.0441 (4)
H8	0.3260 (12)	1.273 (4)	0.3063 (10)	0.058 (5)*
O1	0.16399 (7)	0.8972 (3)	0.28643 (6)	0.0510 (4)
H1A	0.1443 (14)	0.756 (5)	0.3172 (12)	0.092 (8)*
O2	0.28563 (7)	0.8919 (3)	0.37767 (6)	0.0589 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0361 (8)	0.0567 (11)	0.0505 (9)	−0.0060 (8)	0.0136 (7)	0.0079 (8)
C2	0.0431 (9)	0.0544 (11)	0.0443 (8)	−0.0005 (8)	0.0128 (7)	0.0108 (8)
C3	0.0464 (8)	0.0361 (9)	0.0409 (7)	−0.0037 (7)	0.0225 (6)	−0.0009 (6)
C4	0.0390 (8)	0.0486 (10)	0.0464 (8)	−0.0087 (7)	0.0151 (7)	0.0018 (7)
C5	0.0437 (9)	0.0494 (10)	0.0405 (8)	−0.0044 (7)	0.0117 (7)	0.0069 (7)
C6	0.0592 (11)	0.0388 (10)	0.0497 (9)	−0.0072 (8)	0.0293 (8)	0.0007 (7)
N1	0.0419 (7)	0.0448 (8)	0.0431 (7)	−0.0051 (6)	0.0176 (5)	0.0053 (6)
C7	0.0389 (8)	0.0445 (9)	0.0411 (8)	−0.0037 (7)	0.0145 (6)	0.0030 (7)
C8	0.0378 (8)	0.0472 (10)	0.0470 (8)	−0.0083 (7)	0.0135 (6)	0.0040 (7)
O1	0.0415 (6)	0.0588 (8)	0.0488 (6)	−0.0133 (5)	0.0094 (5)	0.0157 (6)
O2	0.0492 (7)	0.0725 (9)	0.0480 (7)	−0.0093 (6)	0.0064 (5)	0.0173 (6)

Geometric parameters (Å, º)

C1—H1	0.99 (2)	C5—N1	1.336 (2)
C1—C2	1.379 (2)	C6—C6^i	1.526 (3)
C1—N1	1.329 (2)	C6—H6A	1.01 (2)
C2—H2	0.990 (19)	C6—H6B	0.99 (2)
C2—C3	1.382 (2)	C7—C8	1.485 (2)
C3—C4	1.383 (2)	C7—O1	1.3066 (18)
C3—C6	1.502 (2)	C7—O2	1.2114 (18)
C4—H4	0.969 (18)	C8—C8^ii	1.308 (3)
C4—C5	1.378 (2)	C8—H8	0.943 (19)
C5—H5	0.976 (19)	O1—H1A	1.03 (3)
C2—C1—H1	120.8 (12)	C3—C6—C6^i	111.16 (17)
N1—C1—H1	116.4 (12)	C3—C6—H6A	110.3 (12)
N1—C1—C2	122.72 (15)	C3—C6—H6B	110.7 (12)
C1—C2—H2	119.0 (11)	C6^i—C6—H6A	108.5 (12)
C1—C2—C3	119.77 (15)	C6^i—C6—H6B	106.3 (12)
C3—C2—H2	121.3 (11)	H6A—C6—H6B	109.8 (17)
C2—C3—C4	117.30 (14)	C1—N1—C5	117.85 (14)
C2—C3—C6	121.12 (15)	O1—C7—C8	114.05 (13)
C4—C3—C6	121.54 (15)	O2—C7—C8	121.47 (14)
C3—C4—H4	122.5 (11)	O2—C7—O1	124.48 (15)
C5—C4—C3	119.70 (15)	C7—C8—H8	115.6 (11)
C5—C4—H4	117.8 (11)	C8^ii—C8—C7	124.52 (19)
C4—C5—H5	119.5 (12)	C8^ii—C8—H8	119.9 (12)
N1—C5—C4	122.66 (15)	C7—O1—H1A	110.9 (12)
N1—C5—H5	117.9 (12)
C1—C2—C3—C4	0.2 (3)	C4—C3—C6—C6^i	−92.8 (2)
C1—C2—C3—C6	−177.60 (16)	C4—C5—N1—C1	−0.3 (3)
C2—C1—N1—C5	0.6 (3)	C6—C3—C4—C5	177.91 (15)
C2—C3—C4—C5	0.2 (2)	N1—C1—C2—C3	−0.6 (3)
C2—C3—C6—C6^i	84.8 (2)	O1—C7—C8—C8^ii	−2.9 (3)
C3—C4—C5—N1	−0.1 (3)	O2—C7—C8—C8^ii	177.1 (2)

Symmetry codes: (i) −x, −y, −z+1; (ii) −x+1/2, −y+5/2, −z+1/2.

4,4'-Ethane-1,2-diyldipyridine succinic acid (ETYSUC_064)

Crystal data

C12H12N2·C4H6O4	F(000) = 640
Mr = 302.32	Dx = 1.405 Mg m^−3
Monoclinic, I2/a	Mo Kα radiation, λ = 0.71073 Å
a = 16.60 (4) Å	Cell parameters from 682 reflections
b = 4.7781 (4) Å	θ = 4.3–19.7°
c = 19.218 (9) Å	µ = 0.10 mm^−1
β = 110.32 (13)°	T = 295 K
V = 1429 (4) Å^3	Plate, colourless
Z = 4	0.35 × 0.16 × 0.03 mm

Data collection

Xcalibur, Eos diffractometer	283 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	167 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.089
Detector resolution: 16.1544 pixels mm^-1	θmax = 25.8°, θmin = 4.4°
ω scans	h = −7→7
Absorption correction: gaussian CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022) Numerical absorption correction based on gaussian integration over a multifaceted crystal model (Absorb Angel (2004) J. Appl. Cryst. 37:486-492)	k = −5→5
Tmin = 0.996, Tmax = 0.997	l = −23→23
1787 measured reflections

Refinement

Refinement on F^2	Primary atom site location: iterative
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.080	H-atom parameters constrained
wR(F^2) = 0.227	w = 1/[σ^2(Fo^2) + (0.1079P)^2 + 4.6707P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
283 reflections	Δρmax = 0.17 e Å^−3
46 parameters	Δρmin = −0.21 e Å^−3
5 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
N1	0.3938 (16)	0.4584 (18)	0.1458 (6)	0.030 (3)*
C2	0.3417 (18)	0.593 (2)	0.0856 (6)	0.050 (4)*
H2	0.2836	0.5477	0.0679	0.060*
C3	0.3715 (18)	0.797 (2)	0.0486 (7)	0.037 (4)*
H3	0.3332	0.8858	0.0073	0.044*
C4	0.4580 (18)	0.867 (2)	0.0733 (7)	0.027 (4)*
C5	0.509 (2)	0.7278 (19)	0.1338 (7)	0.039 (3)*
H5	0.5679	0.7650	0.1519	0.047*
C6	0.4762 (17)	0.533 (3)	0.1687 (8)	0.040 (4)*
H6	0.5136	0.4477	0.2111	0.048*
C1A	0.2571 (17)	0.023 (2)	0.1771 (8)	0.026 (3)*
O1A	0.3340 (16)	0.0941 (16)	0.2114 (6)	0.048 (3)*
H1A	0.3453	0.2345	0.1920	0.072*
C2A	0.2168 (19)	−0.2037 (18)	0.2117 (6)	0.031 (3)*
H2AA	0.2003	−0.3638	0.1787	0.037*
H2AB	0.1656	−0.1304	0.2186	0.037*
O2A	0.2106 (18)	0.1355 (14)	0.1189 (6)	0.049 (3)*
C7	0.490 (2)	1.0714 (18)	0.0311 (7)	0.033 (3)*
H7A	0.5421	1.1598	0.0642	0.039*
H7B	0.4476	1.2160	0.0109	0.039*

Geometric parameters (Å, º)

N1—C2	1.343 (17)	C1A—O1A	1.26 (2)
N1—C6	1.33 (2)	C1A—C2A	1.54 (2)
C2—H2	0.9300	C1A—O2A	1.24 (2)
C2—C3	1.395 (15)	O1A—H1A	0.8200
C3—H3	0.9300	C2A—C2A^i	1.57 (4)
C3—C4	1.39 (2)	C2A—H2AA	0.9700
C4—C5	1.35 (3)	C2A—H2AB	0.9700
C4—C7	1.48 (2)	C7—C7^ii	1.50 (2)
C5—H5	0.9300	C7—H7A	0.9700
C5—C6	1.37 (2)	C7—H7B	0.9700
C6—H6	0.9300
C6—N1—C2	115.9 (15)	O1A—C1A—C2A	118.4 (15)
N1—C2—H2	118.8	O2A—C1A—O1A	123.6 (16)
N1—C2—C3	122 (2)	O2A—C1A—C2A	118 (2)
C3—C2—H2	118.8	C1A—O1A—H1A	109.5
C2—C3—H3	119.9	C1A—C2A—C2A^i	110 (3)
C4—C3—C2	120.2 (16)	C1A—C2A—H2AA	109.8
C4—C3—H3	119.9	C1A—C2A—H2AB	109.8
C3—C4—C7	120.0 (16)	C2A^i—C2A—H2AA	109.8
C5—C4—C3	116.2 (19)	C2A^i—C2A—H2AB	109.8
C5—C4—C7	124 (3)	H2AA—C2A—H2AB	108.2
C4—C5—H5	119.5	C4—C7—C7^ii	110.6 (11)
C4—C5—C6	121 (3)	C4—C7—H7A	109.5
C6—C5—H5	119.5	C4—C7—H7B	109.5
N1—C6—C5	124.1 (19)	C7^ii—C7—H7A	109.5
N1—C6—H6	117.9	C7^ii—C7—H7B	109.5
C5—C6—H6	117.9	H7A—C7—H7B	108.1
N1—C2—C3—C4	0.5 (18)	C4—C5—C6—N1	2.2 (19)
C2—N1—C6—C5	−1.8 (19)	C5—C4—C7—C7^ii	91 (3)
C2—C3—C4—C5	−0.1 (19)	C6—N1—C2—C3	0.4 (16)
C2—C3—C4—C7	176.3 (8)	O1A—C1A—C2A—C2A^i	2 (2)
C3—C4—C5—C6	−1.2 (17)	O2A—C1A—C2A—C2A^i	−174.3 (13)
C3—C4—C7—C7^ii	−85 (3)	C7—C4—C5—C6	−177.4 (10)

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

4,4'-Ethane-1,2-diyldipyridine succinic acid (ETYSUC_094)

Crystal data

C12H12N2·C4H6O4	F(000) = 640
Mr = 302.32	Dx = 1.433 Mg m^−3
Monoclinic, I2/a	Mo Kα radiation, λ = 0.71073 Å
a = 16.56 (3) Å	Cell parameters from 763 reflections
b = 4.7226 (3) Å	θ = 4.3–21.9°
c = 19.187 (7) Å	µ = 0.10 mm^−1
β = 110.99 (11)°	T = 295 K
V = 1401 (3) Å^3	Plate, colourless
Z = 4	0.35 × 0.16 × 0.03 mm

Data collection

Xcalibur, Eos diffractometer	307 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	165 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.099
Detector resolution: 16.1544 pixels mm^-1	θmax = 26.2°, θmin = 4.4°
ω scans	h = −7→7
Absorption correction: gaussian CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022) Numerical absorption correction based on gaussian integration over a multifaceted crystal model (Absorb Angel (2004) J. Appl. Cryst. 37:486-492)	k = −5→5
Tmin = 0.996, Tmax = 0.997	l = −23→22
2114 measured reflections

Refinement

Refinement on F^2	Primary atom site location: iterative
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.087	H-atom parameters constrained
wR(F^2) = 0.265	w = 1/[σ^2(Fo^2) + (0.1368P)^2 + 1.254P] where P = (Fo^2 + 2Fc^2)/3
S = 1.12	(Δ/σ)max < 0.001
307 reflections	Δρmax = 0.19 e Å^−3
46 parameters	Δρmin = −0.28 e Å^−3
6 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
N1	0.3930 (17)	0.463 (2)	0.1454 (6)	0.038 (4)*
C2	0.3402 (19)	0.601 (2)	0.0865 (7)	0.052 (4)*
H2	0.2815	0.5583	0.0697	0.062*
C3	0.369 (3)	0.806 (3)	0.0487 (8)	0.041 (5)*
H3	0.3297	0.9028	0.0084	0.050*
C4	0.462 (3)	0.866 (2)	0.0742 (9)	0.025 (4)*
C5	0.512 (2)	0.7280 (19)	0.1345 (8)	0.044 (3)*
H5	0.5706	0.7642	0.1538	0.052*
C6	0.4770 (17)	0.529 (2)	0.1698 (8)	0.039 (5)*
H6	0.5142	0.4392	0.2123	0.047*
C1A	0.2565 (17)	0.021 (2)	0.1764 (8)	0.029 (4)*
O1A	0.3338 (16)	0.0969 (16)	0.2116 (6)	0.047 (3)*
H1A	0.3483	0.2142	0.1868	0.071*
C2A	0.219 (2)	−0.2040 (17)	0.2123 (7)	0.035 (3)*
H2AA	0.1670	−0.1321	0.2173	0.042*
H2AB	0.2040	−0.3676	0.1796	0.042*
O2A	0.2101 (18)	0.1399 (13)	0.1177 (6)	0.049 (3)*
C7	0.493 (2)	1.0741 (18)	0.0314 (7)	0.035 (3)*
H7A	0.5465	1.1600	0.0637	0.042*
H7B	0.4502	1.2226	0.0124	0.042*

Geometric parameters (Å, º)

N1—C2	1.326 (17)	C1A—O1A	1.27 (2)
N1—C6	1.34 (2)	C1A—C2A	1.51 (2)
C2—H2	0.9300	C1A—O2A	1.25 (2)
C2—C3	1.390 (16)	O1A—H1A	0.8200
C3—H3	0.9300	C2A—C2A^i	1.50 (4)
C3—C4	1.48 (6)	C2A—H2AA	0.9700
C4—C5	1.32 (3)	C2A—H2AB	0.9700
C4—C7	1.479 (16)	C7—C7^ii	1.48 (2)
C5—H5	0.9300	C7—H7A	0.9700
C5—C6	1.393 (16)	C7—H7B	0.9700
C6—H6	0.9300
C2—N1—C6	117.9 (15)	O1A—C1A—C2A	117.0 (15)
N1—C2—H2	118.5	O2A—C1A—O1A	122.2 (16)
N1—C2—C3	123 (2)	O2A—C1A—C2A	121 (2)
C3—C2—H2	118.5	C1A—O1A—H1A	109.5
C2—C3—H3	120.9	C1A—C2A—H2AA	108.9
C2—C3—C4	118 (2)	C1A—C2A—H2AB	108.9
C4—C3—H3	120.9	C2A^i—C2A—C1A	114 (3)
C3—C4—C7	118 (2)	C2A^i—C2A—H2AA	108.9
C5—C4—C3	115.9 (17)	C2A^i—C2A—H2AB	108.9
C5—C4—C7	126 (3)	H2AA—C2A—H2AB	107.7
C4—C5—H5	119.1	C4—C7—C7^ii	108.8 (11)
C4—C5—C6	122 (3)	C4—C7—H7A	109.9
C6—C5—H5	119.1	C4—C7—H7B	109.9
N1—C6—C5	123.0 (18)	C7^ii—C7—H7A	109.9
N1—C6—H6	118.5	C7^ii—C7—H7B	109.9
C5—C6—H6	118.5	H7A—C7—H7B	108.3
N1—C2—C3—C4	2 (2)	C4—C5—C6—N1	0.6 (19)
C2—N1—C6—C5	−2 (2)	C5—C4—C7—C7^ii	95 (3)
C2—C3—C4—C5	−4 (2)	C6—N1—C2—C3	1.1 (18)
C2—C3—C4—C7	176.9 (8)	O1A—C1A—C2A—C2A^i	3 (2)
C3—C4—C5—C6	2 (2)	O2A—C1A—C2A—C2A^i	−172.1 (15)
C3—C4—C7—C7^ii	−86 (3)	C7—C4—C5—C6	−178.1 (11)

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

4,4'-Ethane-1,2-diyldipyridine succinic acid (etysuc_100K)

Crystal data

C12H12N2·C4H6O4	F(000) = 640
Mr = 302.32	Dx = 1.369 Mg m^−3
Monoclinic, I2/a	Cu Kα radiation, λ = 1.54184 Å
a = 16.6147 (11) Å	Cell parameters from 991 reflections
b = 4.8463 (4) Å	θ = 5.6–71.8°
c = 19.3274 (11) Å	µ = 0.82 mm^−1
β = 109.551 (7)°	T = 100 K
V = 1466.51 (19) Å^3	Plate, colourless
Z = 4	0.14 × 0.09 × 0.04 mm

Data collection

SuperNova, Single source at offset/far, Atlas diffractometer	1405 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source	997 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.054
Detector resolution: 10.5384 pixels mm^-1	θmax = 71.9°, θmin = 5.7°
ω scans	h = −20→19
Absorption correction: gaussian CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −5→5
Tmin = 0.898, Tmax = 1.000	l = −17→23
2776 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.065	w = 1/[σ^2(Fo^2) + (0.1064P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.187	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.35 e Å^−3
1405 reflections	Δρmin = −0.31 e Å^−3
137 parameters	Extinction correction: SHELXL-2014/7 (Sheldrick 2014, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0021 (6)

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
N1	0.39213 (14)	0.4635 (5)	0.14561 (10)	0.0303 (6)
C2	0.34035 (18)	0.5944 (7)	0.08632 (13)	0.0322 (7)
C3	0.36893 (18)	0.7944 (7)	0.04871 (14)	0.0324 (7)
C4	0.45523 (17)	0.8634 (6)	0.07289 (12)	0.0288 (7)
C5	0.50902 (17)	0.7271 (6)	0.13411 (13)	0.0304 (7)
C6	0.47548 (17)	0.5314 (6)	0.16897 (13)	0.0309 (7)
C1A	0.25373 (17)	0.0232 (6)	0.17679 (12)	0.0284 (6)
O1A	0.33311 (12)	0.0961 (4)	0.21234 (9)	0.0332 (6)
C2A	0.22030 (17)	−0.2066 (6)	0.21238 (13)	0.0288 (7)
O2A	0.20946 (12)	0.1301 (4)	0.11904 (9)	0.0348 (6)
C7	0.48946 (18)	1.0716 (6)	0.03140 (13)	0.0316 (7)
H2	0.2762 (19)	0.532 (6)	0.0677 (14)	0.028 (7)*
H1A	0.353 (3)	0.232 (9)	0.182 (2)	0.071 (12)*
H2AA	0.208 (2)	−0.369 (8)	0.1766 (18)	0.048 (9)*
H2AB	0.166 (2)	−0.148 (8)	0.2147 (18)	0.050 (10)*
H7A	0.545 (2)	1.166 (7)	0.0671 (16)	0.030 (7)*
H6	0.515 (2)	0.428 (7)	0.2157 (16)	0.036 (8)*
H3	0.328 (2)	0.898 (8)	0.0045 (17)	0.048 (9)*
H7B	0.443 (2)	1.223 (8)	0.0088 (18)	0.047 (9)*
H5	0.570 (2)	0.757 (7)	0.1541 (15)	0.036 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0359 (12)	0.0365 (15)	0.0240 (10)	0.0004 (10)	0.0176 (9)	0.0012 (9)
C2	0.0347 (13)	0.0410 (19)	0.0269 (11)	0.0003 (13)	0.0182 (11)	0.0019 (11)
C3	0.0360 (14)	0.0405 (19)	0.0271 (12)	0.0003 (13)	0.0188 (11)	0.0039 (11)
C4	0.0373 (14)	0.0340 (17)	0.0225 (11)	0.0002 (12)	0.0198 (10)	−0.0016 (10)
C5	0.0346 (14)	0.0363 (17)	0.0261 (12)	−0.0007 (13)	0.0178 (11)	−0.0006 (11)
C6	0.0366 (14)	0.0361 (17)	0.0244 (11)	−0.0010 (12)	0.0161 (11)	0.0016 (11)
C1A	0.0345 (13)	0.0319 (17)	0.0241 (11)	0.0010 (12)	0.0170 (10)	−0.0005 (10)
O1A	0.0339 (10)	0.0404 (13)	0.0275 (9)	−0.0063 (9)	0.0132 (8)	0.0051 (8)
C2A	0.0313 (13)	0.0319 (17)	0.0274 (12)	−0.0014 (11)	0.0154 (11)	0.0027 (11)
O2A	0.0370 (10)	0.0426 (13)	0.0283 (9)	−0.0016 (9)	0.0157 (8)	0.0048 (9)
C7	0.0384 (14)	0.0350 (18)	0.0285 (12)	−0.0016 (12)	0.0205 (11)	0.0005 (11)

Geometric parameters (Å, º)

N1—C2	1.340 (4)	C1A—O1A	1.315 (3)
N1—C6	1.346 (3)	C1A—C2A	1.509 (4)
C2—C3	1.387 (4)	C1A—O2A	1.227 (3)
C2—H2	1.05 (3)	O1A—H1A	1.00 (4)
C3—C4	1.392 (4)	C2A—C2A^i	1.518 (5)
C3—H3	1.03 (4)	C2A—H2AA	1.02 (4)
C4—C5	1.388 (4)	C2A—H2AB	0.97 (4)
C4—C7	1.513 (4)	C7—C7^ii	1.537 (5)
C5—C6	1.384 (4)	C7—H7A	1.05 (3)
C5—H5	0.97 (3)	C7—H7B	1.05 (4)
C6—H6	1.05 (3)
C2—N1—C6	117.7 (2)	O1A—C1A—C2A	114.7 (2)
N1—C2—C3	123.0 (3)	O2A—C1A—O1A	123.6 (3)
N1—C2—H2	116.3 (16)	O2A—C1A—C2A	121.7 (2)
C3—C2—H2	120.6 (16)	C1A—O1A—H1A	110 (2)
C2—C3—C4	119.1 (3)	C1A—C2A—C2A^i	114.9 (3)
C2—C3—H3	122 (2)	C1A—C2A—H2AA	106.3 (19)
C4—C3—H3	119 (2)	C1A—C2A—H2AB	107 (2)
C3—C4—C7	120.7 (2)	C2A^i—C2A—H2AA	111 (2)
C5—C4—C3	118.0 (2)	C2A^i—C2A—H2AB	111 (2)
C5—C4—C7	121.3 (2)	H2AA—C2A—H2AB	106 (3)
C4—C5—H5	124.0 (19)	C4—C7—C7^ii	110.0 (3)
C6—C5—C4	119.4 (2)	C4—C7—H7A	110.0 (16)
C6—C5—H5	116.5 (19)	C4—C7—H7B	109.2 (19)
N1—C6—C5	122.7 (2)	C7^ii—C7—H7A	109.7 (16)
N1—C6—H6	116.9 (17)	C7^ii—C7—H7B	108.6 (18)
C5—C6—H6	120.3 (17)	H7A—C7—H7B	109 (3)
N1—C2—C3—C4	0.3 (4)	C4—C5—C6—N1	0.7 (4)
C2—N1—C6—C5	−0.5 (4)	C5—C4—C7—C7^ii	92.0 (3)
C2—C3—C4—C5	0.0 (4)	C6—N1—C2—C3	−0.1 (4)
C2—C3—C4—C7	177.4 (2)	O1A—C1A—C2A—C2A^i	6.8 (4)
C3—C4—C5—C6	−0.5 (4)	O2A—C1A—C2A—C2A^i	−173.5 (3)
C3—C4—C7—C7^ii	−85.3 (4)	C7—C4—C5—C6	−177.8 (2)

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

1,2-bis(4,4'-pyridyl)ethane succinic acid (ETYSUC_140K_B)

Crystal data

C12H12N2·C4H6O4	F(000) = 640
Mr = 302.32	Dx = 1.363 Mg m^−3
Monoclinic, I2/a	Cu Kα radiation, λ = 1.54184 Å
a = 16.6128 (4) Å	Cell parameters from 2580 reflections
b = 4.8607 (1) Å	θ = 4.3–71.4°
c = 19.3367 (5) Å	µ = 0.82 mm^−1
β = 109.370 (3)°	T = 140 K
V = 1473.05 (7) Å^3	Plate, colourless
Z = 4	0.45 × 0.41 × 0.14 mm

Data collection

New Xcalibur, EosS2 diffractometer	1405 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Cu) X-ray Source	1293 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
Detector resolution: 8.0294 pixels mm^-1	θmax = 71.4°, θmin = 4.9°
ω scans	h = −19→20
Absorption correction: gaussian CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −5→5
Tmin = 0.768, Tmax = 0.923	l = −23→23
4200 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	All H-atom parameters refined
wR(F^2) = 0.113	w = 1/[σ^2(Fo^2) + (0.0768P)^2 + 0.5548P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
1405 reflections	Δρmax = 0.21 e Å^−3
136 parameters	Δρmin = −0.28 e Å^−3

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
N1	0.39249 (6)	0.4633 (2)	0.14537 (5)	0.0209 (3)
C2	0.34083 (7)	0.5912 (3)	0.08599 (7)	0.0232 (3)
C3	0.36929 (8)	0.7906 (3)	0.04867 (7)	0.0228 (3)
C4	0.45529 (8)	0.8616 (2)	0.07264 (6)	0.0195 (3)
C5	0.50888 (7)	0.7268 (3)	0.13387 (7)	0.0214 (3)
C6	0.47531 (8)	0.5314 (3)	0.16862 (7)	0.0217 (3)
C1A	0.25381 (7)	0.0232 (2)	0.17648 (6)	0.0191 (3)
O1A	0.33304 (5)	0.09416 (19)	0.21198 (5)	0.0261 (3)
C2A	0.22052 (7)	−0.2066 (3)	0.21244 (6)	0.0213 (3)
O2A	0.21009 (5)	0.12863 (19)	0.11954 (5)	0.0265 (3)
C7	0.48918 (8)	1.0697 (3)	0.03154 (7)	0.0221 (3)
H2AA	0.2098 (10)	−0.361 (4)	0.1792 (9)	0.032 (4)*
H2AB	0.1637 (10)	−0.143 (3)	0.2131 (9)	0.030 (4)*
H6	0.5115 (9)	0.433 (3)	0.2105 (8)	0.027 (4)*
H2	0.2804 (9)	0.536 (3)	0.0694 (8)	0.024 (4)*
H3	0.3304 (9)	0.881 (3)	0.0082 (8)	0.022 (4)*
H7A	0.5416 (10)	1.151 (3)	0.0645 (9)	0.027 (4)*
H5	0.5699 (9)	0.763 (3)	0.1523 (8)	0.024 (4)*
H7B	0.4465 (11)	1.214 (4)	0.0116 (9)	0.036 (4)*
H1A	0.3537 (13)	0.241 (5)	0.1825 (12)	0.068 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0223 (5)	0.0215 (6)	0.0204 (5)	−0.0028 (4)	0.0091 (4)	0.0014 (4)
C2	0.0178 (6)	0.0276 (7)	0.0245 (6)	−0.0018 (5)	0.0075 (5)	0.0020 (5)
C3	0.0204 (6)	0.0265 (7)	0.0207 (6)	0.0008 (5)	0.0057 (5)	0.0040 (5)
C4	0.0238 (6)	0.0180 (6)	0.0199 (6)	−0.0020 (4)	0.0114 (5)	−0.0021 (4)
C5	0.0191 (6)	0.0225 (6)	0.0228 (6)	−0.0031 (5)	0.0071 (5)	−0.0017 (5)
C6	0.0222 (6)	0.0222 (6)	0.0191 (6)	−0.0005 (5)	0.0047 (5)	0.0020 (5)
C1A	0.0196 (6)	0.0186 (6)	0.0197 (6)	−0.0004 (5)	0.0071 (5)	−0.0010 (4)
O1A	0.0211 (5)	0.0301 (5)	0.0240 (5)	−0.0079 (4)	0.0034 (4)	0.0081 (4)
C2A	0.0185 (6)	0.0205 (6)	0.0239 (7)	−0.0031 (5)	0.0059 (5)	0.0019 (5)
O2A	0.0231 (5)	0.0287 (5)	0.0247 (5)	−0.0013 (3)	0.0039 (4)	0.0080 (4)
C7	0.0262 (6)	0.0187 (6)	0.0242 (6)	−0.0028 (5)	0.0119 (5)	0.0006 (5)

Geometric parameters (Å, º)

N1—C2	1.3370 (16)	C1A—O1A	1.3128 (14)
N1—C6	1.3396 (15)	C1A—C2A	1.5139 (16)
C2—C3	1.3820 (17)	C1A—O2A	1.2133 (15)
C2—H2	0.985 (15)	O1A—H1A	1.04 (2)
C3—C4	1.3913 (17)	C2A—C2A^i	1.518 (2)
C3—H3	0.942 (15)	C2A—H2AA	0.964 (18)
C4—C5	1.3872 (17)	C2A—H2AB	0.997 (16)
C4—C7	1.5060 (16)	C7—C7^ii	1.538 (2)
C5—C6	1.3833 (17)	C7—H7A	0.977 (16)
C5—H5	0.972 (14)	C7—H7B	0.981 (18)
C6—H6	0.960 (16)
C2—N1—C6	117.94 (10)	O1A—C1A—C2A	114.17 (10)
N1—C2—C3	122.76 (11)	O2A—C1A—O1A	123.93 (11)
N1—C2—H2	116.6 (9)	O2A—C1A—C2A	121.90 (10)
C3—C2—H2	120.7 (9)	C1A—O1A—H1A	110.5 (12)
C2—C3—C4	119.43 (11)	C1A—C2A—C2A^i	115.25 (12)
C2—C3—H3	120.1 (9)	C1A—C2A—H2AA	106.3 (10)
C4—C3—H3	120.4 (9)	C1A—C2A—H2AB	105.6 (9)
C3—C4—C7	120.87 (11)	C2A^i—C2A—H2AA	109.9 (10)
C5—C4—C3	117.69 (11)	C2A^i—C2A—H2AB	112.7 (9)
C5—C4—C7	121.40 (11)	H2AA—C2A—H2AB	106.4 (13)
C4—C5—H5	121.7 (9)	C4—C7—C7^ii	110.45 (12)
C6—C5—C4	119.39 (11)	C4—C7—H7A	109.7 (10)
C6—C5—H5	118.9 (9)	C4—C7—H7B	109.9 (10)
N1—C6—C5	122.78 (11)	C7^ii—C7—H7A	107.7 (10)
N1—C6—H6	116.5 (9)	C7^ii—C7—H7B	109.4 (10)
C5—C6—H6	120.7 (9)	H7A—C7—H7B	109.6 (13)
N1—C2—C3—C4	0.74 (19)	C4—C5—C6—N1	0.56 (19)
C2—N1—C6—C5	0.02 (18)	C5—C4—C7—C7^ii	92.45 (16)
C2—C3—C4—C5	−0.14 (18)	C6—N1—C2—C3	−0.67 (19)
C2—C3—C4—C7	177.52 (11)	O1A—C1A—C2A—C2A^i	7.09 (19)
C3—C4—C5—C6	−0.47 (18)	O2A—C1A—C2A—C2A^i	−173.30 (13)
C3—C4—C7—C7^ii	−85.12 (16)	C7—C4—C5—C6	−178.12 (11)

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

4,4'-Ethane-1,2-diyldipyridine succinic acid (ETYSUC_141)

Crystal data

C12H12N2·C4H6O4	F(000) = 640
Mr = 302.32	Dx = 1.481 Mg m^−3
Monoclinic, I2/a	Mo Kα radiation, λ = 0.71073 Å
a = 16.55 (3) Å	Cell parameters from 771 reflections
b = 4.6266 (3) Å	θ = 4.4–22.1°
c = 19.089 (6) Å	µ = 0.11 mm^−1
β = 111.96 (9)°	T = 295 K
V = 1356 (2) Å^3	Plank, colourless
Z = 4	0.37 × 0.16 × 0.03 mm

Data collection

Xcalibur, Eos diffractometer	282 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	177 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.099
Detector resolution: 16.1544 pixels mm^-1	θmax = 26.3°, θmin = 2.3°
ω scans	h = −6→6
Absorption correction: gaussian CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022) Numerical absorption correction based on gaussian integration over a multifaceted crystal model (Absorb Angel (2004) J. Appl. Cryst. 37:486-492)	k = −5→5
Tmin = 0.996, Tmax = 0.996	l = −23→21
1943 measured reflections

Refinement

Refinement on F^2	9 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.091	H-atom parameters constrained
wR(F^2) = 0.274	w = 1/[σ^2(Fo^2) + (0.1778P)^2 + 0.1765P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max < 0.001
282 reflections	Δρmax = 0.22 e Å^−3
46 parameters	Δρmin = −0.29 e Å^−3

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
N1	0.3945 (17)	0.4679 (19)	0.1472 (6)	0.036 (4)*
C2	0.3397 (17)	0.6075 (18)	0.0866 (6)	0.042 (3)*
H2	0.2805	0.5660	0.0696	0.051*
C3	0.3690 (16)	0.813 (2)	0.0486 (7)	0.041 (4)*
H3	0.3299	0.9083	0.0069	0.049*
C4	0.4572 (14)	0.873 (2)	0.0737 (6)	0.021 (3)*
C5	0.5135 (16)	0.7284 (19)	0.1349 (5)	0.040 (3)*
H5	0.5731	0.7633	0.1523	0.048*
C6	0.4792 (18)	0.528 (2)	0.1702 (8)	0.043 (5)*
H6	0.5173	0.4311	0.2121	0.051*
C1A	0.2570 (15)	0.028 (2)	0.1769 (6)	0.022 (3)*
O1A	0.3358 (15)	0.1010 (15)	0.2125 (6)	0.052 (3)*
H1A	0.3539	0.1883	0.1839	0.077*
C2A	0.2193 (19)	−0.2023 (19)	0.2116 (6)	0.037 (3)*
H2AA	0.1664	−0.1288	0.2159	0.045*
H2AB	0.2036	−0.3685	0.1783	0.045*
O2A	0.2072 (14)	0.1469 (12)	0.1168 (4)	0.044 (2)*
C7	0.489 (2)	1.0781 (19)	0.0303 (7)	0.035 (3)*
H7A	0.5400	1.1775	0.0643	0.042*
H7B	0.4441	1.2216	0.0067	0.042*

Geometric parameters (Å, º)

N1—C2	1.338 (16)	C1A—O1A	1.270 (19)
N1—C6	1.33 (2)	C1A—C2A	1.51 (2)
C2—H2	0.9300	C1A—O2A	1.262 (15)
C2—C3	1.387 (15)	O1A—H1A	0.8200
C3—H3	0.9300	C2A—C2A^i	1.50 (3)
C3—C4	1.38 (2)	C2A—H2AA	0.9700
C4—C5	1.365 (16)	C2A—H2AB	0.9700
C4—C7	1.479 (15)	C7—C7^ii	1.52 (3)
C5—H5	0.9300	C7—H7A	0.9700
C5—C6	1.385 (16)	C7—H7B	0.9700
C6—H6	0.9300
C6—N1—C2	118.2 (16)	O1A—C1A—C2A	117.7 (12)
N1—C2—H2	119.2	O2A—C1A—O1A	124.1 (14)
N1—C2—C3	122 (2)	O2A—C1A—C2A	118.0 (18)
C3—C2—H2	119.2	C1A—O1A—H1A	109.5
C2—C3—H3	120.4	C1A—C2A—H2AA	108.9
C4—C3—C2	119.1 (16)	C1A—C2A—H2AB	108.9
C4—C3—H3	120.4	C2A^i—C2A—C1A	113 (3)
C3—C4—C7	118.9 (14)	C2A^i—C2A—H2AA	108.9
C5—C4—C3	119.5 (14)	C2A^i—C2A—H2AB	108.9
C5—C4—C7	121.5 (18)	H2AA—C2A—H2AB	107.7
C4—C5—H5	121.0	C4—C7—C7^ii	111.1 (9)
C4—C5—C6	118.0 (18)	C4—C7—H7A	109.4
C6—C5—H5	121.0	C4—C7—H7B	109.4
N1—C6—C5	123.5 (16)	C7^ii—C7—H7A	109.4
N1—C6—H6	118.2	C7^ii—C7—H7B	109.4
C5—C6—H6	118.2	H7A—C7—H7B	108.0
N1—C2—C3—C4	0.4 (17)	C4—C5—C6—N1	0.7 (18)
C2—N1—C6—C5	0 (2)	C5—C4—C7—C7^ii	86 (3)
C2—C3—C4—C5	0.4 (18)	C6—N1—C2—C3	−0.7 (17)
C2—C3—C4—C7	176.2 (8)	O1A—C1A—C2A—C2A^i	4 (2)
C3—C4—C5—C6	−0.9 (16)	O2A—C1A—C2A—C2A^i	−171.7 (15)
C3—C4—C7—C7^ii	−90 (3)	C7—C4—C5—C6	−176.6 (9)

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

1,2-bis(4,4'-pyridyl)ethane succinic acid (ETYSUC_145K_B)

Crystal data

C12H12N2·C4H6O4	F(000) = 640
Mr = 302.32	Dx = 1.362 Mg m^−3
Monoclinic, I2/a	Cu Kα radiation, λ = 1.54184 Å
a = 16.6153 (5) Å	Cell parameters from 2569 reflections
b = 4.8619 (1) Å	θ = 4.3–71.4°
c = 19.3400 (5) Å	µ = 0.82 mm^−1
β = 109.350 (3)°	T = 145 K
V = 1474.07 (7) Å^3	Plate, colourless
Z = 4	0.45 × 0.41 × 0.14 mm

Data collection

New Xcalibur, EosS2 diffractometer	1405 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Cu) X-ray Source	1300 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
Detector resolution: 8.0294 pixels mm^-1	θmax = 71.4°, θmin = 4.9°
ω scans	h = −19→20
Absorption correction: gaussian CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −5→5
Tmin = 0.769, Tmax = 0.923	l = −23→23
4199 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	All H-atom parameters refined
wR(F^2) = 0.114	w = 1/[σ^2(Fo^2) + (0.0775P)^2 + 0.5583P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
1405 reflections	Δρmax = 0.20 e Å^−3
136 parameters	Δρmin = −0.28 e Å^−3

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
N1	0.39247 (6)	0.4632 (2)	0.14530 (5)	0.0217 (3)
C2	0.34088 (8)	0.5908 (3)	0.08600 (7)	0.0239 (3)
C3	0.36930 (8)	0.7901 (3)	0.04859 (7)	0.0236 (3)
C4	0.45529 (8)	0.8615 (2)	0.07261 (6)	0.0200 (3)
C5	0.50885 (7)	0.7265 (3)	0.13389 (7)	0.0220 (3)
C6	0.47532 (8)	0.5314 (3)	0.16861 (7)	0.0223 (3)
C1A	0.25379 (7)	0.0232 (2)	0.17647 (6)	0.0194 (3)
O1A	0.33310 (5)	0.09372 (19)	0.21193 (5)	0.0267 (3)
C2A	0.22053 (7)	−0.2066 (3)	0.21248 (7)	0.0220 (3)
O2A	0.21016 (5)	0.12828 (19)	0.11956 (5)	0.0274 (3)
C7	0.48914 (8)	1.0694 (3)	0.03150 (7)	0.0225 (3)
H2AA	0.2096 (10)	−0.361 (4)	0.1785 (9)	0.034 (4)*
H3	0.3300 (9)	0.883 (3)	0.0077 (8)	0.021 (3)*
H6	0.5109 (9)	0.435 (3)	0.2106 (8)	0.023 (4)*
H2AB	0.1643 (10)	−0.144 (3)	0.2139 (9)	0.030 (4)*
H2	0.2803 (9)	0.534 (3)	0.0698 (8)	0.024 (4)*
H7A	0.5415 (10)	1.152 (3)	0.0651 (9)	0.030 (4)*
H5	0.5703 (9)	0.760 (3)	0.1518 (8)	0.023 (4)*
H7B	0.4463 (10)	1.214 (4)	0.0111 (9)	0.032 (4)*
H1A	0.3544 (13)	0.242 (5)	0.1825 (12)	0.070 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0227 (5)	0.0220 (6)	0.0217 (5)	−0.0028 (4)	0.0092 (4)	0.0015 (4)
C2	0.0187 (6)	0.0274 (7)	0.0257 (6)	−0.0020 (5)	0.0076 (5)	0.0018 (5)
C3	0.0215 (6)	0.0268 (7)	0.0217 (6)	0.0014 (5)	0.0062 (5)	0.0044 (5)
C4	0.0243 (6)	0.0182 (6)	0.0204 (6)	−0.0015 (4)	0.0115 (5)	−0.0019 (4)
C5	0.0198 (6)	0.0231 (6)	0.0231 (6)	−0.0032 (5)	0.0071 (5)	−0.0015 (5)
C6	0.0228 (6)	0.0230 (6)	0.0193 (6)	−0.0010 (5)	0.0048 (5)	0.0022 (5)
C1A	0.0197 (6)	0.0185 (6)	0.0206 (6)	−0.0005 (5)	0.0073 (5)	−0.0009 (5)
O1A	0.0215 (5)	0.0303 (5)	0.0251 (5)	−0.0082 (4)	0.0034 (4)	0.0083 (4)
C2A	0.0189 (6)	0.0214 (7)	0.0248 (7)	−0.0030 (5)	0.0061 (5)	0.0027 (5)
O2A	0.0238 (5)	0.0297 (5)	0.0253 (5)	−0.0018 (3)	0.0038 (4)	0.0084 (4)
C7	0.0266 (6)	0.0192 (6)	0.0241 (6)	−0.0032 (5)	0.0117 (5)	0.0007 (5)

Geometric parameters (Å, º)

N1—C2	1.3354 (16)	C1A—O1A	1.3136 (14)
N1—C6	1.3405 (15)	C1A—C2A	1.5145 (16)
C2—C3	1.3829 (17)	C1A—O2A	1.2120 (15)
C2—H2	0.989 (14)	O1A—H1A	1.05 (2)
C3—C4	1.3920 (17)	C2A—C2A^i	1.517 (2)
C3—H3	0.955 (15)	C2A—H2AA	0.973 (18)
C4—C5	1.3886 (17)	C2A—H2AB	0.991 (16)
C4—C7	1.5054 (16)	C7—C7^ii	1.537 (2)
C5—C6	1.3819 (17)	C7—H7A	0.982 (17)
C5—H5	0.977 (14)	C7—H7B	0.985 (17)
C6—H6	0.953 (15)
C2—N1—C6	117.99 (10)	O1A—C1A—C2A	114.09 (10)
N1—C2—C3	122.80 (11)	O2A—C1A—O1A	123.98 (11)
N1—C2—H2	116.0 (9)	O2A—C1A—C2A	121.93 (10)
C3—C2—H2	121.2 (9)	C1A—O1A—H1A	110.9 (12)
C2—C3—C4	119.39 (11)	C1A—C2A—C2A^i	115.28 (12)
C2—C3—H3	120.3 (9)	C1A—C2A—H2AA	105.8 (10)
C4—C3—H3	120.2 (9)	C1A—C2A—H2AB	106.2 (10)
C3—C4—C7	120.86 (11)	C2A^i—C2A—H2AA	110.4 (10)
C5—C4—C3	117.63 (11)	C2A^i—C2A—H2AB	111.9 (9)
C5—C4—C7	121.47 (11)	H2AA—C2A—H2AB	106.7 (13)
C4—C5—H5	121.5 (9)	C4—C7—C7^ii	110.55 (12)
C6—C5—C4	119.45 (11)	C4—C7—H7A	109.1 (10)
C6—C5—H5	119.0 (9)	C4—C7—H7B	110.1 (9)
N1—C6—C5	122.75 (11)	C7^ii—C7—H7A	108.3 (10)
N1—C6—H6	116.3 (9)	C7^ii—C7—H7B	109.0 (10)
C5—C6—H6	120.9 (9)	H7A—C7—H7B	109.8 (13)
N1—C2—C3—C4	0.63 (19)	C4—C5—C6—N1	0.59 (19)
C2—N1—C6—C5	−0.02 (18)	C5—C4—C7—C7^ii	92.42 (16)
C2—C3—C4—C5	−0.03 (18)	C6—N1—C2—C3	−0.60 (19)
C2—C3—C4—C7	177.54 (11)	O1A—C1A—C2A—C2A^i	7.19 (19)
C3—C4—C5—C6	−0.54 (18)	O2A—C1A—C2A—C2A^i	−173.42 (13)
C3—C4—C7—C7^ii	−85.06 (16)	C7—C4—C5—C6	−178.10 (11)

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

1,2-bis(4,4'-pyridyl)ethane succinic acid (ETYSUC_150K_B)

Crystal data

C12H12N2·C4H6O4	F(000) = 640
Mr = 302.32	Dx = 1.361 Mg m^−3
Monoclinic, I2/a	Cu Kα radiation, λ = 1.54184 Å
a = 16.6155 (4) Å	Cell parameters from 2565 reflections
b = 4.8646 (1) Å	θ = 4.3–71.3°
c = 19.3384 (5) Å	µ = 0.82 mm^−1
β = 109.321 (3)°	T = 150 K
V = 1475.05 (7) Å^3	Plate, colourless
Z = 4	0.45 × 0.41 × 0.14 mm

Data collection

New Xcalibur, EosS2 diffractometer	1406 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Cu) X-ray Source	1302 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
Detector resolution: 8.0294 pixels mm^-1	θmax = 71.4°, θmin = 4.9°
ω scans	h = −19→20
Absorption correction: gaussian CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −5→5
Tmin = 0.769, Tmax = 0.923	l = −23→23
4196 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.042	All H-atom parameters refined
wR(F^2) = 0.117	w = 1/[σ^2(Fo^2) + (0.0789P)^2 + 0.4183P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
1406 reflections	Δρmax = 0.20 e Å^−3
136 parameters	Δρmin = −0.26 e Å^−3

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
N1	0.39248 (6)	0.4630 (2)	0.14532 (5)	0.0222 (3)
C2	0.34094 (7)	0.5903 (3)	0.08596 (7)	0.0246 (3)
C3	0.36932 (7)	0.7898 (3)	0.04861 (7)	0.0241 (3)
C4	0.45529 (8)	0.8613 (2)	0.07261 (6)	0.0206 (3)
C5	0.50881 (7)	0.7265 (3)	0.13383 (7)	0.0227 (3)
C6	0.47532 (8)	0.5312 (3)	0.16858 (7)	0.0229 (3)
C1A	0.25392 (7)	0.0230 (2)	0.17656 (6)	0.0201 (3)
O1A	0.33313 (5)	0.09365 (19)	0.21189 (5)	0.0276 (3)
C2A	0.22049 (7)	−0.2064 (3)	0.21251 (7)	0.0224 (3)
O2A	0.21024 (5)	0.1282 (2)	0.11962 (5)	0.0284 (3)
C7	0.48914 (8)	1.0693 (3)	0.03159 (7)	0.0231 (3)
H2AA	0.2102 (10)	−0.358 (4)	0.1788 (9)	0.032 (4)*
H2AB	0.1634 (10)	−0.144 (3)	0.2130 (8)	0.029 (4)*
H6	0.5107 (9)	0.435 (3)	0.2107 (8)	0.025 (4)*
H2	0.2800 (10)	0.535 (3)	0.0686 (9)	0.028 (4)*
H3	0.3301 (9)	0.881 (3)	0.0081 (8)	0.023 (4)*
H7A	0.5419 (10)	1.150 (3)	0.0648 (9)	0.031 (4)*
H5	0.5700 (9)	0.761 (3)	0.1518 (8)	0.023 (4)*
H7B	0.4456 (11)	1.212 (4)	0.0109 (9)	0.038 (4)*
H1A	0.3543 (13)	0.237 (5)	0.1823 (12)	0.066 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0229 (5)	0.0229 (6)	0.0220 (5)	−0.0029 (4)	0.0090 (4)	0.0015 (4)
C2	0.0194 (6)	0.0285 (7)	0.0260 (6)	−0.0024 (5)	0.0078 (5)	0.0025 (5)
C3	0.0210 (6)	0.0281 (7)	0.0219 (6)	0.0008 (5)	0.0055 (5)	0.0046 (5)
C4	0.0247 (6)	0.0187 (6)	0.0214 (6)	−0.0016 (4)	0.0119 (5)	−0.0020 (4)
C5	0.0193 (6)	0.0240 (7)	0.0246 (6)	−0.0033 (5)	0.0069 (5)	−0.0016 (5)
C6	0.0227 (6)	0.0237 (6)	0.0208 (6)	−0.0004 (5)	0.0052 (5)	0.0026 (5)
C1A	0.0204 (6)	0.0196 (6)	0.0210 (6)	−0.0006 (5)	0.0076 (5)	−0.0009 (5)
O1A	0.0221 (5)	0.0316 (6)	0.0258 (5)	−0.0087 (4)	0.0033 (4)	0.0084 (4)
C2A	0.0194 (6)	0.0219 (7)	0.0249 (7)	−0.0038 (5)	0.0059 (5)	0.0023 (5)
O2A	0.0248 (5)	0.0306 (5)	0.0265 (5)	−0.0014 (4)	0.0041 (4)	0.0091 (4)
C7	0.0271 (6)	0.0200 (6)	0.0247 (6)	−0.0027 (5)	0.0121 (5)	0.0009 (5)

Geometric parameters (Å, º)

N1—C2	1.3358 (16)	C1A—O1A	1.3123 (14)
N1—C6	1.3408 (15)	C1A—C2A	1.5141 (16)
C2—C3	1.3823 (17)	C1A—O2A	1.2133 (15)
C2—H2	0.992 (15)	O1A—H1A	1.04 (2)
C3—C4	1.3921 (17)	C2A—C2A^i	1.518 (2)
C3—H3	0.947 (15)	C2A—H2AA	0.962 (18)
C4—C5	1.3875 (17)	C2A—H2AB	0.999 (15)
C4—C7	1.5050 (16)	C7—C7^ii	1.539 (2)
C5—C6	1.3824 (17)	C7—H7A	0.982 (17)
C5—H5	0.974 (13)	C7—H7B	0.986 (18)
C6—H6	0.954 (15)
C2—N1—C6	117.94 (10)	O1A—C1A—C2A	114.26 (10)
N1—C2—C3	122.82 (11)	O2A—C1A—O1A	123.91 (11)
N1—C2—H2	117.2 (9)	O2A—C1A—C2A	121.82 (10)
C3—C2—H2	119.9 (9)	C1A—O1A—H1A	110.7 (11)
C2—C3—C4	119.40 (11)	C1A—C2A—C2A^i	115.20 (12)
C2—C3—H3	120.0 (9)	C1A—C2A—H2AA	105.3 (10)
C4—C3—H3	120.6 (9)	C1A—C2A—H2AB	106.0 (9)
C3—C4—C7	120.89 (11)	C2A^i—C2A—H2AA	110.3 (10)
C5—C4—C3	117.62 (11)	C2A^i—C2A—H2AB	113.0 (9)
C5—C4—C7	121.44 (11)	H2AA—C2A—H2AB	106.3 (13)
C4—C5—H5	121.5 (9)	C4—C7—C7^ii	110.52 (12)
C6—C5—C4	119.47 (11)	C4—C7—H7A	109.5 (10)
C6—C5—H5	119.0 (9)	C4—C7—H7B	109.5 (10)
N1—C6—C5	122.73 (11)	C7^ii—C7—H7A	107.5 (10)
N1—C6—H6	116.1 (9)	C7^ii—C7—H7B	108.6 (10)
C5—C6—H6	121.2 (9)	H7A—C7—H7B	111.2 (14)
N1—C2—C3—C4	0.8 (2)	C4—C5—C6—N1	0.56 (19)
C2—N1—C6—C5	0.11 (18)	C5—C4—C7—C7^ii	92.51 (16)
C2—C3—C4—C5	−0.07 (18)	C6—N1—C2—C3	−0.78 (19)
C2—C3—C4—C7	177.54 (11)	O1A—C1A—C2A—C2A^i	7.00 (19)
C3—C4—C5—C6	−0.55 (18)	O2A—C1A—C2A—C2A^i	−173.52 (13)
C3—C4—C7—C7^ii	−85.01 (17)	C7—C4—C5—C6	−178.16 (11)

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

4,4'-Ethane-1,2-diyldipyridine succinic acid (etysuc_150K)

Crystal data

C12H12N2·C4H6O4	F(000) = 640
Mr = 302.32	Dx = 1.360 Mg m^−3
Monoclinic, I2/a	Cu Kα radiation, λ = 1.54184 Å
a = 16.6252 (13) Å	Cell parameters from 1036 reflections
b = 4.8647 (4) Å	θ = 4.9–71.0°
c = 19.3379 (11) Å	µ = 0.82 mm^−1
β = 109.278 (8)°	T = 150 K
V = 1476.3 (2) Å^3	Plate, colourless
Z = 4	0.14 × 0.09 × 0.04 mm

Data collection

SuperNova, Single source at offset/far, Atlas diffractometer	1416 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source	954 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.037
Detector resolution: 10.5384 pixels mm^-1	θmax = 71.9°, θmin = 4.9°
ω scans	h = −20→19
Absorption correction: gaussian CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −5→5
Tmin = 0.903, Tmax = 1.000	l = −17→23
2791 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.060	w = 1/[σ^2(Fo^2) + (0.1111P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.190	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.25 e Å^−3
1416 reflections	Δρmin = −0.25 e Å^−3
137 parameters	Extinction correction: SHELXL-2014/7 (Sheldrick 2014, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0029 (7)

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
N1	0.39256 (15)	0.4616 (5)	0.14538 (11)	0.0380 (6)
C2	0.34048 (18)	0.5894 (7)	0.08568 (14)	0.0392 (7)
C3	0.36912 (19)	0.7911 (7)	0.04844 (15)	0.0400 (8)
C4	0.45518 (18)	0.8607 (6)	0.07254 (13)	0.0354 (7)
C5	0.50865 (18)	0.7270 (7)	0.13396 (14)	0.0376 (7)
C6	0.47557 (19)	0.5309 (7)	0.16895 (14)	0.0395 (7)
C1A	0.25352 (17)	0.0224 (6)	0.17656 (13)	0.0351 (7)
O1A	0.33312 (13)	0.0934 (5)	0.21189 (10)	0.0434 (6)
C2A	0.22084 (18)	−0.2054 (7)	0.21293 (15)	0.0379 (7)
O2A	0.21002 (13)	0.1287 (5)	0.11946 (9)	0.0450 (6)
C7	0.4890 (2)	1.0700 (6)	0.03152 (14)	0.0391 (7)
H2	0.276 (2)	0.529 (6)	0.0682 (15)	0.038 (8)*
H1A	0.357 (3)	0.230 (9)	0.181 (2)	0.087 (14)*
H2AA	0.209 (3)	−0.367 (9)	0.179 (2)	0.071 (11)*
H2AB	0.164 (2)	−0.159 (7)	0.2148 (16)	0.045 (8)*
H7A	0.546 (2)	1.165 (8)	0.0676 (19)	0.056 (9)*
H6	0.515 (2)	0.431 (6)	0.2177 (16)	0.042 (8)*
H3	0.329 (2)	0.891 (7)	0.0009 (17)	0.054 (9)*
H7B	0.442 (2)	1.214 (8)	0.0068 (18)	0.053 (9)*
H5	0.571 (2)	0.751 (7)	0.1524 (15)	0.045 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0416 (13)	0.0440 (15)	0.0354 (11)	−0.0011 (11)	0.0220 (10)	0.0017 (10)
C2	0.0382 (15)	0.0495 (19)	0.0352 (12)	−0.0008 (14)	0.0191 (12)	0.0051 (12)
C3	0.0414 (15)	0.0485 (19)	0.0359 (13)	−0.0010 (14)	0.0205 (12)	0.0042 (13)
C4	0.0409 (15)	0.0408 (17)	0.0326 (12)	−0.0009 (13)	0.0229 (11)	−0.0007 (12)
C5	0.0393 (16)	0.0445 (18)	0.0346 (13)	−0.0017 (14)	0.0198 (12)	0.0016 (12)
C6	0.0429 (16)	0.0454 (18)	0.0344 (12)	−0.0003 (14)	0.0186 (12)	0.0018 (12)
C1A	0.0362 (14)	0.0428 (17)	0.0301 (11)	−0.0004 (13)	0.0160 (11)	0.0002 (12)
O1A	0.0411 (12)	0.0534 (14)	0.0362 (9)	−0.0079 (10)	0.0135 (9)	0.0081 (9)
C2A	0.0375 (15)	0.0427 (18)	0.0390 (13)	−0.0025 (13)	0.0199 (12)	0.0038 (13)
O2A	0.0432 (12)	0.0554 (15)	0.0386 (10)	−0.0012 (10)	0.0162 (9)	0.0084 (10)
C7	0.0481 (17)	0.0400 (18)	0.0379 (13)	−0.0016 (14)	0.0260 (13)	0.0018 (12)

Geometric parameters (Å, º)

N1—C2	1.345 (4)	C1A—O1A	1.319 (3)
N1—C6	1.346 (4)	C1A—C2A	1.507 (4)
C2—C3	1.391 (4)	C1A—O2A	1.218 (3)
C2—H2	1.05 (3)	O1A—H1A	1.05 (5)
C3—C4	1.392 (4)	C2A—C2A^i	1.505 (6)
C3—H3	1.06 (3)	C2A—H2AA	1.00 (4)
C4—C5	1.388 (4)	C2A—H2AB	0.99 (3)
C4—C7	1.508 (4)	C7—C7^ii	1.542 (5)
C5—C6	1.384 (4)	C7—H7A	1.08 (4)
C5—H5	0.99 (3)	C7—H7B	1.04 (4)
C6—H6	1.07 (3)
C2—N1—C6	118.2 (2)	O1A—C1A—C2A	113.9 (2)
N1—C2—C3	122.5 (3)	O2A—C1A—O1A	123.5 (3)
N1—C2—H2	116.4 (16)	O2A—C1A—C2A	122.5 (3)
C3—C2—H2	121.1 (16)	C1A—O1A—H1A	112 (2)
C2—C3—C4	119.2 (3)	C1A—C2A—H2AA	108 (2)
C2—C3—H3	123 (2)	C1A—C2A—H2AB	110.4 (19)
C4—C3—H3	117.5 (19)	C2A^i—C2A—C1A	116.0 (3)
C3—C4—C7	120.5 (3)	C2A^i—C2A—H2AA	109 (2)
C5—C4—C3	118.0 (2)	C2A^i—C2A—H2AB	110.9 (17)
C5—C4—C7	121.5 (3)	H2AA—C2A—H2AB	102 (3)
C4—C5—H5	123.5 (18)	C4—C7—C7^ii	110.2 (3)
C6—C5—C4	119.7 (3)	C4—C7—H7A	110.4 (18)
C6—C5—H5	116.5 (18)	C4—C7—H7B	110.0 (18)
N1—C6—C5	122.4 (3)	C7^ii—C7—H7A	108.2 (19)
N1—C6—H6	116.6 (16)	C7^ii—C7—H7B	105.8 (18)
C5—C6—H6	121.0 (17)	H7A—C7—H7B	112 (3)
N1—C2—C3—C4	1.4 (4)	C4—C5—C6—N1	0.5 (4)
C2—N1—C6—C5	−0.1 (4)	C5—C4—C7—C7^ii	92.7 (4)
C2—C3—C4—C5	−1.0 (4)	C6—N1—C2—C3	−0.8 (4)
C2—C3—C4—C7	177.4 (3)	O1A—C1A—C2A—C2A^i	6.6 (4)
C3—C4—C5—C6	0.1 (4)	O2A—C1A—C2A—C2A^i	−173.8 (3)
C3—C4—C7—C7^ii	−85.7 (4)	C7—C4—C5—C6	−178.3 (3)

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

1,2-bis(4,4'-pyridyl)ethane succinic acid (ETYSUC_155K_B)

Crystal data

C12H12N2·C4H6O4	F(000) = 640
Mr = 302.32	Dx = 1.360 Mg m^−3
Monoclinic, I2/a	Cu Kα radiation, λ = 1.54184 Å
a = 16.6176 (4) Å	Cell parameters from 2558 reflections
b = 4.8671 (1) Å	θ = 4.3–71.3°
c = 19.3394 (5) Å	µ = 0.82 mm^−1
β = 109.301 (3)°	T = 155 K
V = 1476.25 (7) Å^3	Plate, colourless
Z = 4	0.45 × 0.4 × 0.14 mm

Data collection

New Xcalibur, EosS2 diffractometer	1408 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Cu) X-ray Source	1286 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
Detector resolution: 8.0294 pixels mm^-1	θmax = 71.4°, θmin = 4.9°
ω scans	h = −19→20
Absorption correction: gaussian CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −5→5
Tmin = 0.769, Tmax = 0.923	l = −23→23
4200 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.042	All H-atom parameters refined
wR(F^2) = 0.118	w = 1/[σ^2(Fo^2) + (0.0807P)^2 + 0.4039P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max < 0.001
1408 reflections	Δρmax = 0.21 e Å^−3
136 parameters	Δρmin = −0.28 e Å^−3

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
N1	0.39255 (6)	0.4628 (2)	0.14530 (6)	0.0226 (3)
C2	0.34103 (7)	0.5899 (3)	0.08596 (7)	0.0250 (3)
C3	0.36934 (8)	0.7896 (3)	0.04856 (7)	0.0248 (3)
C4	0.45527 (8)	0.8610 (2)	0.07256 (6)	0.0208 (3)
C5	0.50879 (7)	0.7266 (3)	0.13383 (7)	0.0229 (3)
C6	0.47526 (8)	0.5314 (3)	0.16854 (7)	0.0233 (3)
C1A	0.25392 (7)	0.0231 (2)	0.17650 (6)	0.0202 (3)
O1A	0.33315 (5)	0.09332 (19)	0.21185 (5)	0.0282 (3)
C2A	0.22058 (7)	−0.2063 (3)	0.21252 (7)	0.0230 (3)
O2A	0.21031 (5)	0.1279 (2)	0.11965 (5)	0.0289 (3)
C7	0.48911 (8)	1.0692 (3)	0.03156 (7)	0.0235 (3)
H2AA	0.2094 (10)	−0.359 (4)	0.1793 (10)	0.037 (4)*
H6	0.5112 (9)	0.435 (3)	0.2105 (8)	0.027 (4)*
H3	0.3299 (9)	0.882 (3)	0.0075 (8)	0.025 (4)*
H2AB	0.1637 (11)	−0.141 (4)	0.2128 (9)	0.036 (4)*
H2	0.2800 (10)	0.534 (3)	0.0692 (9)	0.029 (4)*
H7A	0.5419 (11)	1.148 (3)	0.0654 (10)	0.032 (4)*
H5	0.5702 (9)	0.761 (3)	0.1517 (8)	0.025 (4)*
H7B	0.4465 (11)	1.211 (4)	0.0107 (9)	0.038 (4)*
H1A	0.3540 (14)	0.239 (5)	0.1817 (12)	0.073 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0238 (5)	0.0233 (6)	0.0222 (5)	−0.0032 (4)	0.0096 (4)	0.0015 (4)
C2	0.0191 (6)	0.0296 (7)	0.0261 (6)	−0.0022 (5)	0.0073 (5)	0.0031 (5)
C3	0.0222 (6)	0.0286 (7)	0.0227 (6)	0.0008 (5)	0.0063 (5)	0.0051 (5)
C4	0.0254 (6)	0.0191 (6)	0.0212 (6)	−0.0020 (4)	0.0121 (5)	−0.0019 (4)
C5	0.0198 (6)	0.0242 (7)	0.0245 (6)	−0.0033 (5)	0.0073 (5)	−0.0016 (5)
C6	0.0235 (6)	0.0242 (6)	0.0209 (6)	−0.0012 (5)	0.0056 (5)	0.0019 (5)
C1A	0.0202 (6)	0.0199 (6)	0.0210 (6)	−0.0007 (5)	0.0073 (5)	−0.0009 (5)
O1A	0.0227 (5)	0.0324 (6)	0.0259 (5)	−0.0086 (4)	0.0033 (4)	0.0087 (4)
C2A	0.0199 (6)	0.0223 (7)	0.0259 (7)	−0.0037 (5)	0.0063 (5)	0.0023 (5)
O2A	0.0254 (5)	0.0314 (5)	0.0264 (5)	−0.0017 (4)	0.0040 (4)	0.0090 (4)
C7	0.0277 (6)	0.0203 (6)	0.0252 (7)	−0.0036 (5)	0.0123 (5)	0.0005 (5)

Geometric parameters (Å, º)

N1—C2	1.3355 (16)	C1A—O1A	1.3125 (14)
N1—C6	1.3395 (16)	C1A—C2A	1.5143 (16)
C2—C3	1.3832 (18)	C1A—O2A	1.2116 (15)
C2—H2	0.994 (15)	O1A—H1A	1.05 (3)
C3—C4	1.3918 (17)	C2A—C2A^i	1.517 (2)
C3—H3	0.958 (16)	C2A—H2AA	0.958 (19)
C4—C5	1.3880 (17)	C2A—H2AB	0.999 (17)
C4—C7	1.5056 (16)	C7—C7^ii	1.539 (2)
C5—C6	1.3823 (17)	C7—H7A	0.983 (17)
C5—H5	0.978 (14)	C7—H7B	0.977 (19)
C6—H6	0.957 (15)
C2—N1—C6	117.90 (11)	O1A—C1A—C2A	114.15 (10)
N1—C2—C3	122.86 (11)	O2A—C1A—O1A	123.99 (11)
N1—C2—H2	116.7 (10)	O2A—C1A—C2A	121.86 (10)
C3—C2—H2	120.4 (9)	C1A—O1A—H1A	110.3 (12)
C2—C3—C4	119.33 (11)	C1A—C2A—C2A^i	115.34 (12)
C2—C3—H3	120.3 (9)	C1A—C2A—H2AA	106.4 (10)
C4—C3—H3	120.3 (9)	C1A—C2A—H2AB	105.1 (10)
C3—C4—C7	120.88 (11)	C2A^i—C2A—H2AA	110.1 (10)
C5—C4—C3	117.66 (11)	C2A^i—C2A—H2AB	113.3 (10)
C5—C4—C7	121.42 (11)	H2AA—C2A—H2AB	106.0 (14)
C4—C5—H5	121.3 (9)	C4—C7—C7^ii	110.47 (12)
C6—C5—C4	119.41 (11)	C4—C7—H7A	108.6 (10)
C6—C5—H5	119.2 (9)	C4—C7—H7B	110.4 (10)
N1—C6—C5	122.82 (11)	C7^ii—C7—H7A	107.9 (10)
N1—C6—H6	116.5 (9)	C7^ii—C7—H7B	108.1 (10)
C5—C6—H6	120.7 (9)	H7A—C7—H7B	111.3 (14)
N1—C2—C3—C4	0.8 (2)	C4—C5—C6—N1	0.57 (19)
C2—N1—C6—C5	0.03 (19)	C5—C4—C7—C7^ii	92.60 (16)
C2—C3—C4—C5	−0.19 (18)	C6—N1—C2—C3	−0.75 (19)
C2—C3—C4—C7	177.57 (11)	O1A—C1A—C2A—C2A^i	7.09 (19)
C3—C4—C5—C6	−0.47 (18)	O2A—C1A—C2A—C2A^i	−173.51 (14)
C3—C4—C7—C7^ii	−85.08 (17)	C7—C4—C5—C6	−178.22 (11)

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

1,2-bis(4,4'-pyridyl)ethane succinic acid (ETYSUC_160K_B)

Crystal data

C12H12N2·C4H6O4	F(000) = 640
Mr = 302.32	Dx = 1.359 Mg m^−3
Monoclinic, I2/a	Cu Kα radiation, λ = 1.54184 Å
a = 16.6174 (3) Å	Cell parameters from 2560 reflections
b = 4.8695 (1) Å	θ = 4.3–71.2°
c = 19.3375 (4) Å	µ = 0.82 mm^−1
β = 109.268 (2)°	T = 160 K
V = 1477.11 (5) Å^3	Plate, colourless
Z = 4	0.45 × 0.4 × 0.14 mm

Data collection

New Xcalibur, EosS2 diffractometer	1407 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Cu) X-ray Source	1279 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
Detector resolution: 8.0294 pixels mm^-1	θmax = 71.5°, θmin = 4.9°
ω scans	h = −19→20
Absorption correction: gaussian CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −5→5
Tmin = 0.770, Tmax = 0.923	l = −23→23
4202 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	All H-atom parameters refined
wR(F^2) = 0.118	w = 1/[σ^2(Fo^2) + (0.0795P)^2 + 0.4169P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
1407 reflections	Δρmax = 0.19 e Å^−3
136 parameters	Δρmin = −0.27 e Å^−3

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
N1	0.39257 (6)	0.4625 (2)	0.14527 (6)	0.0233 (3)
C2	0.34112 (8)	0.5896 (3)	0.08592 (7)	0.0255 (3)
C3	0.36942 (8)	0.7891 (3)	0.04857 (7)	0.0253 (3)
C4	0.45526 (8)	0.8606 (2)	0.07255 (6)	0.0213 (3)
C5	0.50880 (8)	0.7266 (3)	0.13382 (7)	0.0237 (3)
C6	0.47525 (8)	0.5315 (3)	0.16856 (7)	0.0240 (3)
C1A	0.25394 (7)	0.0226 (2)	0.17650 (6)	0.0210 (3)
O1A	0.33317 (5)	0.0932 (2)	0.21183 (5)	0.0289 (3)
C2A	0.22055 (7)	−0.2064 (3)	0.21259 (7)	0.0235 (3)
O2A	0.21036 (5)	0.1279 (2)	0.11967 (5)	0.0298 (3)
C7	0.48913 (8)	1.0692 (3)	0.03152 (7)	0.0242 (3)
H2AA	0.2096 (10)	−0.357 (4)	0.1788 (10)	0.039 (4)*
H6	0.5112 (9)	0.435 (3)	0.2108 (8)	0.023 (3)*
H2	0.2804 (9)	0.531 (3)	0.0684 (8)	0.026 (4)*
H3	0.3298 (10)	0.879 (3)	0.0078 (9)	0.029 (4)*
H7A	0.5425 (10)	1.150 (3)	0.0656 (9)	0.030 (4)*
H2AB	0.1636 (10)	−0.148 (4)	0.2130 (9)	0.036 (4)*
H5	0.5699 (9)	0.764 (3)	0.1519 (8)	0.026 (4)*
H7B	0.4454 (11)	1.210 (4)	0.0103 (9)	0.038 (4)*
H1A	0.3544 (14)	0.237 (5)	0.1819 (12)	0.077 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0238 (5)	0.0241 (6)	0.0231 (5)	−0.0031 (4)	0.0095 (4)	0.0019 (4)
C2	0.0198 (6)	0.0299 (7)	0.0273 (6)	−0.0023 (5)	0.0081 (5)	0.0028 (5)
C3	0.0225 (6)	0.0297 (7)	0.0232 (6)	0.0005 (5)	0.0067 (5)	0.0050 (5)
C4	0.0254 (6)	0.0199 (6)	0.0219 (6)	−0.0022 (4)	0.0123 (5)	−0.0019 (4)
C5	0.0207 (6)	0.0255 (7)	0.0248 (6)	−0.0041 (5)	0.0075 (5)	−0.0016 (5)
C6	0.0239 (6)	0.0252 (7)	0.0215 (6)	−0.0016 (5)	0.0055 (5)	0.0026 (5)
C1A	0.0210 (6)	0.0205 (6)	0.0220 (6)	−0.0006 (5)	0.0078 (5)	−0.0008 (5)
O1A	0.0230 (5)	0.0334 (6)	0.0269 (5)	−0.0090 (4)	0.0034 (4)	0.0090 (4)
C2A	0.0201 (6)	0.0234 (7)	0.0260 (7)	−0.0038 (5)	0.0063 (5)	0.0027 (5)
O2A	0.0257 (5)	0.0325 (6)	0.0277 (5)	−0.0019 (4)	0.0040 (4)	0.0094 (4)
C7	0.0284 (6)	0.0210 (7)	0.0264 (7)	−0.0035 (5)	0.0133 (5)	0.0004 (5)

Geometric parameters (Å, º)

N1—C2	1.3355 (16)	C1A—O1A	1.3133 (14)
N1—C6	1.3398 (16)	C1A—C2A	1.5145 (16)
C2—C3	1.3823 (18)	C1A—O2A	1.2122 (15)
C2—H2	0.995 (15)	O1A—H1A	1.04 (3)
C3—C4	1.3909 (17)	C2A—C2A^i	1.516 (2)
C3—H3	0.949 (16)	C2A—H2AA	0.959 (19)
C4—C5	1.3876 (17)	C2A—H2AB	0.991 (16)
C4—C7	1.5074 (16)	C7—C7^ii	1.537 (2)
C5—C6	1.3827 (17)	C7—H7A	0.995 (16)
C5—H5	0.975 (14)	C7—H7B	0.985 (18)
C6—H6	0.960 (15)
C2—N1—C6	117.86 (11)	O1A—C1A—C2A	114.18 (10)
N1—C2—C3	122.89 (11)	O2A—C1A—O1A	123.89 (11)
N1—C2—H2	116.7 (9)	O2A—C1A—C2A	121.93 (10)
C3—C2—H2	120.4 (9)	C1A—O1A—H1A	110.6 (12)
C2—C3—C4	119.34 (11)	C1A—C2A—C2A^i	115.28 (12)
C2—C3—H3	119.6 (9)	C1A—C2A—H2AA	105.5 (10)
C4—C3—H3	121.1 (9)	C1A—C2A—H2AB	106.7 (10)
C3—C4—C7	120.87 (11)	C2A^i—C2A—H2AA	110.7 (10)
C5—C4—C3	117.71 (11)	C2A^i—C2A—H2AB	113.0 (10)
C5—C4—C7	121.38 (11)	H2AA—C2A—H2AB	105.0 (14)
C4—C5—H5	121.2 (9)	C4—C7—C7^ii	110.39 (13)
C6—C5—C4	119.36 (11)	C4—C7—H7A	108.9 (10)
C6—C5—H5	119.4 (9)	C4—C7—H7B	109.7 (10)
N1—C6—C5	122.83 (11)	C7^ii—C7—H7A	107.9 (10)
N1—C6—H6	116.4 (8)	C7^ii—C7—H7B	108.0 (10)
C5—C6—H6	120.7 (8)	H7A—C7—H7B	112.0 (14)
N1—C2—C3—C4	0.9 (2)	C4—C5—C6—N1	0.66 (19)
C2—N1—C6—C5	−0.07 (19)	C5—C4—C7—C7^ii	92.68 (16)
C2—C3—C4—C5	−0.23 (18)	C6—N1—C2—C3	−0.70 (19)
C2—C3—C4—C7	177.59 (11)	O1A—C1A—C2A—C2A^i	6.90 (19)
C3—C4—C5—C6	−0.48 (18)	O2A—C1A—C2A—C2A^i	−173.49 (14)
C3—C4—C7—C7^ii	−85.06 (17)	C7—C4—C5—C6	−178.29 (11)

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

1,2-bis(4,4'-pyridyl)ethane succinic acid (ETYSUC_165K_B)

Crystal data

C12H12N2·C4H6O4	F(000) = 640
Mr = 302.32	Dx = 1.358 Mg m^−3
Monoclinic, I2/a	Cu Kα radiation, λ = 1.54184 Å
a = 16.6187 (3) Å	Cell parameters from 2530 reflections
b = 4.8720 (1) Å	θ = 4.3–71.2°
c = 19.3377 (4) Å	µ = 0.82 mm^−1
β = 109.242 (2)°	T = 165 K
V = 1478.23 (5) Å^3	Plate, colourless
Z = 4	0.47 × 0.41 × 0.12 mm

Data collection

New Xcalibur, EosS2 diffractometer	1408 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Cu) X-ray Source	1285 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
Detector resolution: 8.0294 pixels mm^-1	θmax = 71.4°, θmin = 4.8°
ω scans	h = −19→20
Absorption correction: gaussian CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −5→5
Tmin = 0.764, Tmax = 0.922	l = −23→23
4208 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.042	All H-atom parameters refined
wR(F^2) = 0.119	w = 1/[σ^2(Fo^2) + (0.0803P)^2 + 0.5292P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
1408 reflections	Δρmax = 0.20 e Å^−3
136 parameters	Δρmin = −0.29 e Å^−3

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
N1	0.39267 (7)	0.4622 (2)	0.14520 (6)	0.0234 (3)
C2	0.34117 (8)	0.5892 (3)	0.08589 (7)	0.0258 (3)
C3	0.36949 (8)	0.7885 (3)	0.04849 (7)	0.0258 (3)
C4	0.45516 (8)	0.8604 (3)	0.07246 (7)	0.0216 (3)
C5	0.50870 (8)	0.7267 (3)	0.13383 (7)	0.0241 (3)
C6	0.47521 (8)	0.5315 (3)	0.16847 (7)	0.0241 (3)
C1A	0.25400 (7)	0.0224 (3)	0.17653 (7)	0.0213 (3)
O1A	0.33311 (6)	0.0928 (2)	0.21179 (5)	0.0293 (3)
C2A	0.22058 (8)	−0.2064 (3)	0.21254 (7)	0.0242 (3)
O2A	0.21041 (6)	0.1278 (2)	0.11974 (5)	0.0303 (3)
C7	0.48907 (9)	1.0690 (3)	0.03141 (7)	0.0245 (3)
H2AA	0.2089 (11)	−0.358 (4)	0.1786 (10)	0.039 (5)*
H2AB	0.1644 (10)	−0.145 (4)	0.2137 (9)	0.033 (4)*
H6	0.5114 (10)	0.436 (3)	0.2103 (8)	0.027 (4)*
H2	0.2806 (10)	0.532 (3)	0.0699 (9)	0.026 (4)*
H3	0.3297 (10)	0.880 (3)	0.0079 (9)	0.028 (4)*
H7A	0.5413 (11)	1.152 (4)	0.0650 (10)	0.032 (4)*
H5	0.5700 (9)	0.760 (3)	0.1517 (8)	0.027 (4)*
H7B	0.4453 (11)	1.212 (4)	0.0108 (10)	0.038 (4)*
H1A	0.3549 (14)	0.237 (5)	0.1833 (12)	0.068 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0242 (6)	0.0243 (6)	0.0228 (6)	−0.0032 (4)	0.0093 (4)	0.0017 (4)
C2	0.0195 (6)	0.0307 (7)	0.0272 (7)	−0.0031 (5)	0.0078 (5)	0.0033 (5)
C3	0.0230 (6)	0.0300 (7)	0.0235 (7)	0.0010 (5)	0.0062 (5)	0.0054 (5)
C4	0.0261 (6)	0.0202 (6)	0.0221 (6)	−0.0022 (5)	0.0128 (5)	−0.0017 (5)
C5	0.0209 (6)	0.0258 (7)	0.0253 (7)	−0.0034 (5)	0.0074 (5)	−0.0009 (5)
C6	0.0242 (6)	0.0254 (7)	0.0209 (6)	−0.0012 (5)	0.0051 (5)	0.0025 (5)
C1A	0.0214 (6)	0.0205 (6)	0.0225 (6)	−0.0005 (5)	0.0078 (5)	−0.0007 (5)
O1A	0.0232 (5)	0.0339 (6)	0.0271 (5)	−0.0097 (4)	0.0033 (4)	0.0094 (4)
C2A	0.0208 (6)	0.0237 (7)	0.0268 (7)	−0.0038 (5)	0.0061 (5)	0.0030 (5)
O2A	0.0260 (5)	0.0330 (6)	0.0284 (5)	−0.0019 (4)	0.0040 (4)	0.0102 (4)
C7	0.0290 (7)	0.0206 (7)	0.0268 (7)	−0.0038 (5)	0.0134 (6)	0.0007 (5)

Geometric parameters (Å, º)

N1—C2	1.3355 (17)	C1A—O1A	1.3116 (15)
N1—C6	1.3385 (16)	C1A—C2A	1.5135 (17)
C2—C3	1.3828 (18)	C1A—O2A	1.2125 (16)
C2—H2	0.991 (15)	O1A—H1A	1.03 (2)
C3—C4	1.3892 (18)	C2A—C2A^i	1.517 (2)
C3—H3	0.955 (16)	C2A—H2AA	0.965 (19)
C4—C5	1.3886 (18)	C2A—H2AB	0.987 (16)
C4—C7	1.5086 (17)	C7—C7^ii	1.533 (2)
C5—C6	1.3815 (18)	C7—H7A	0.983 (18)
C5—H5	0.976 (14)	C7—H7B	0.992 (19)
C6—H6	0.955 (16)
C2—N1—C6	117.88 (11)	O1A—C1A—C2A	114.23 (11)
N1—C2—C3	122.83 (11)	O2A—C1A—O1A	123.87 (11)
N1—C2—H2	115.7 (9)	O2A—C1A—C2A	121.90 (11)
C3—C2—H2	121.4 (9)	C1A—O1A—H1A	111.7 (12)
C2—C3—C4	119.38 (12)	C1A—C2A—C2A^i	115.26 (13)
C2—C3—H3	119.8 (9)	C1A—C2A—H2AA	105.9 (11)
C4—C3—H3	120.8 (9)	C1A—C2A—H2AB	106.3 (10)
C3—C4—C7	120.92 (12)	C2A^i—C2A—H2AA	110.9 (11)
C5—C4—C3	117.68 (11)	C2A^i—C2A—H2AB	112.3 (10)
C5—C4—C7	121.37 (11)	H2AA—C2A—H2AB	105.5 (14)
C4—C5—H5	121.5 (9)	C4—C7—C7^ii	110.39 (13)
C6—C5—C4	119.35 (11)	C4—C7—H7A	109.2 (10)
C6—C5—H5	119.0 (9)	C4—C7—H7B	109.5 (10)
N1—C6—C5	122.87 (12)	C7^ii—C7—H7A	108.4 (10)
N1—C6—H6	116.8 (9)	C7^ii—C7—H7B	108.9 (10)
C5—C6—H6	120.3 (9)	H7A—C7—H7B	110.4 (14)
N1—C2—C3—C4	0.6 (2)	C4—C5—C6—N1	0.5 (2)
C2—N1—C6—C5	−0.08 (19)	C5—C4—C7—C7^ii	92.68 (17)
C2—C3—C4—C5	−0.17 (19)	C6—N1—C2—C3	−0.5 (2)
C2—C3—C4—C7	177.64 (12)	O1A—C1A—C2A—C2A^i	7.0 (2)
C3—C4—C5—C6	−0.39 (19)	O2A—C1A—C2A—C2A^i	−173.33 (14)
C3—C4—C7—C7^ii	−85.04 (18)	C7—C4—C5—C6	−178.18 (11)

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

1,2-bis(4,4'-pyridyl)ethane succinic acid (ETYSUC_170K_B)

Crystal data

C12H12N2·C4H6O4	F(000) = 640
Mr = 302.32	Dx = 1.357 Mg m^−3
Monoclinic, I2/a	Cu Kα radiation, λ = 1.54184 Å
a = 16.6197 (3) Å	Cell parameters from 2535 reflections
b = 4.8747 (1) Å	θ = 4.3–71.1°
c = 19.3362 (4) Å	µ = 0.82 mm^−1
β = 109.217 (2)°	T = 170 K
V = 1479.25 (5) Å^3	Plate, colourless
Z = 4	0.47 × 0.41 × 0.12 mm

Data collection

New Xcalibur, EosS2 diffractometer	1410 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Cu) X-ray Source	1291 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
Detector resolution: 8.0294 pixels mm^-1	θmax = 71.4°, θmin = 4.8°
ω scans	h = −19→20
Absorption correction: gaussian CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −5→5
Tmin = 0.764, Tmax = 0.922	l = −23→23
4216 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.042	All H-atom parameters refined
wR(F^2) = 0.120	w = 1/[σ^2(Fo^2) + (0.0803P)^2 + 0.5464P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
1410 reflections	Δρmax = 0.19 e Å^−3
136 parameters	Δρmin = −0.28 e Å^−3

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
N1	0.39265 (7)	0.4621 (2)	0.14520 (6)	0.0241 (3)
C2	0.34123 (8)	0.5886 (3)	0.08586 (7)	0.0267 (3)
C3	0.36946 (8)	0.7881 (3)	0.04850 (7)	0.0260 (3)
C4	0.45527 (8)	0.8604 (3)	0.07250 (7)	0.0220 (3)
C5	0.50868 (8)	0.7265 (3)	0.13380 (7)	0.0244 (3)
C6	0.47521 (8)	0.5314 (3)	0.16842 (7)	0.0248 (3)
C1A	0.25406 (7)	0.0224 (3)	0.17653 (7)	0.0216 (3)
O1A	0.33317 (6)	0.0926 (2)	0.21175 (5)	0.0302 (3)
C2A	0.22059 (8)	−0.2063 (3)	0.21254 (7)	0.0246 (3)
O2A	0.21047 (6)	0.1276 (2)	0.11974 (5)	0.0312 (3)
C7	0.48902 (9)	1.0686 (3)	0.03146 (7)	0.0253 (3)
H2AA	0.2091 (11)	−0.358 (4)	0.1789 (10)	0.038 (4)*
H2AB	0.1640 (11)	−0.145 (4)	0.2137 (9)	0.036 (4)*
H6	0.5102 (10)	0.434 (3)	0.2102 (8)	0.027 (4)*
H2	0.2805 (10)	0.528 (3)	0.0686 (9)	0.030 (4)*
H3	0.3306 (10)	0.879 (3)	0.0075 (9)	0.029 (4)*
H7A	0.5423 (11)	1.149 (4)	0.0654 (10)	0.034 (4)*
H5	0.5699 (9)	0.763 (3)	0.1521 (8)	0.028 (4)*
H7B	0.4454 (11)	1.210 (4)	0.0101 (10)	0.039 (4)*
H1A	0.3541 (14)	0.238 (5)	0.1833 (13)	0.073 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0251 (6)	0.0247 (6)	0.0238 (6)	−0.0035 (4)	0.0099 (4)	0.0018 (4)
C2	0.0207 (6)	0.0316 (8)	0.0282 (7)	−0.0027 (5)	0.0083 (5)	0.0032 (5)
C3	0.0231 (6)	0.0303 (7)	0.0236 (7)	0.0011 (5)	0.0064 (5)	0.0059 (5)
C4	0.0263 (6)	0.0207 (7)	0.0223 (6)	−0.0022 (5)	0.0124 (5)	−0.0017 (5)
C5	0.0211 (6)	0.0263 (7)	0.0259 (7)	−0.0042 (5)	0.0077 (5)	−0.0017 (5)
C6	0.0246 (6)	0.0263 (7)	0.0217 (6)	−0.0013 (5)	0.0054 (5)	0.0027 (5)
C1A	0.0217 (6)	0.0208 (6)	0.0227 (6)	−0.0007 (5)	0.0079 (5)	−0.0004 (5)
O1A	0.0240 (5)	0.0350 (6)	0.0279 (5)	−0.0095 (4)	0.0035 (4)	0.0094 (4)
C2A	0.0211 (6)	0.0240 (7)	0.0275 (7)	−0.0038 (5)	0.0066 (5)	0.0030 (5)
O2A	0.0269 (5)	0.0343 (6)	0.0286 (5)	−0.0023 (4)	0.0039 (4)	0.0102 (4)
C7	0.0297 (7)	0.0215 (7)	0.0278 (7)	−0.0036 (5)	0.0138 (6)	0.0005 (5)

Geometric parameters (Å, º)

N1—C2	1.3348 (17)	C1A—O1A	1.3116 (15)
N1—C6	1.3390 (16)	C1A—C2A	1.5140 (17)
C2—C3	1.3824 (18)	C1A—O2A	1.2125 (16)
C2—H2	0.998 (16)	O1A—H1A	1.03 (3)
C3—C4	1.3921 (18)	C2A—C2A^i	1.518 (2)
C3—H3	0.951 (16)	C2A—H2AA	0.961 (19)
C4—C5	1.3880 (18)	C2A—H2AB	0.994 (17)
C4—C7	1.5059 (17)	C7—C7^ii	1.534 (2)
C5—C6	1.3809 (18)	C7—H7A	0.992 (18)
C5—H5	0.978 (15)	C7—H7B	0.987 (19)
C6—H6	0.953 (16)
C2—N1—C6	117.85 (11)	O1A—C1A—C2A	114.24 (11)
N1—C2—C3	122.88 (12)	O2A—C1A—O1A	123.90 (11)
N1—C2—H2	116.3 (10)	O2A—C1A—C2A	121.85 (11)
C3—C2—H2	120.8 (10)	C1A—O1A—H1A	111.2 (12)
C2—C3—C4	119.38 (12)	C1A—C2A—C2A^i	115.26 (13)
C2—C3—H3	120.6 (9)	C1A—C2A—H2AA	106.0 (11)
C4—C3—H3	120.0 (9)	C1A—C2A—H2AB	106.4 (10)
C3—C4—C7	120.89 (12)	C2A^i—C2A—H2AA	110.6 (11)
C5—C4—C3	117.56 (11)	C2A^i—C2A—H2AB	112.3 (10)
C5—C4—C7	121.51 (11)	H2AA—C2A—H2AB	105.6 (14)
C4—C5—H5	121.3 (9)	C4—C7—C7^ii	110.55 (13)
C6—C5—C4	119.44 (11)	C4—C7—H7A	108.9 (10)
C6—C5—H5	119.3 (9)	C4—C7—H7B	110.0 (10)
N1—C6—C5	122.89 (12)	C7^ii—C7—H7A	107.6 (10)
N1—C6—H6	115.5 (9)	C7^ii—C7—H7B	107.9 (10)
C5—C6—H6	121.6 (9)	H7A—C7—H7B	111.9 (14)
N1—C2—C3—C4	0.8 (2)	C4—C5—C6—N1	0.5 (2)
C2—N1—C6—C5	0.09 (19)	C5—C4—C7—C7^ii	92.62 (17)
C2—C3—C4—C5	−0.18 (19)	C6—N1—C2—C3	−0.8 (2)
C2—C3—C4—C7	177.53 (12)	O1A—C1A—C2A—C2A^i	7.0 (2)
C3—C4—C5—C6	−0.46 (19)	O2A—C1A—C2A—C2A^i	−173.39 (14)
C3—C4—C7—C7^ii	−85.01 (18)	C7—C4—C5—C6	−178.16 (11)

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

1,2-bis(4,4'-pyridyl)ethane succinic acid (ETYSUC_175K_B)

Crystal data

C12H12N2·C4H6O4	F(000) = 640
Mr = 302.32	Dx = 1.356 Mg m^−3
Monoclinic, I2/a	Cu Kα radiation, λ = 1.54184 Å
a = 16.6216 (4) Å	Cell parameters from 2515 reflections
b = 4.8770 (1) Å	θ = 4.3–71.1°
c = 19.3388 (4) Å	µ = 0.81 mm^−1
β = 109.193 (2)°	T = 175 K
V = 1480.53 (6) Å^3	Plate, colourless
Z = 4	0.47 × 0.41 × 0.12 mm

Data collection

New Xcalibur, EosS2 diffractometer	1411 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Cu) X-ray Source	1288 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
Detector resolution: 8.0294 pixels mm^-1	θmax = 71.4°, θmin = 4.8°
ω scans	h = −19→20
Absorption correction: gaussian CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −5→5
Tmin = 0.764, Tmax = 0.922	l = −23→23
4215 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.043	All H-atom parameters refined
wR(F^2) = 0.122	w = 1/[σ^2(Fo^2) + (0.0833P)^2 + 0.4278P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
1411 reflections	Δρmax = 0.21 e Å^−3
136 parameters	Δρmin = −0.29 e Å^−3

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
N1	0.39271 (7)	0.4620 (2)	0.14514 (6)	0.0251 (3)
C2	0.34133 (8)	0.5882 (3)	0.08582 (7)	0.0276 (3)
C3	0.36955 (8)	0.7876 (3)	0.04847 (7)	0.0276 (3)
C4	0.45519 (8)	0.8602 (3)	0.07244 (7)	0.0230 (3)
C5	0.50859 (8)	0.7267 (3)	0.13375 (7)	0.0254 (3)
C6	0.47515 (8)	0.5313 (3)	0.16840 (7)	0.0257 (3)
C1A	0.25413 (7)	0.0223 (3)	0.17660 (7)	0.0227 (3)
O1A	0.33319 (6)	0.0923 (2)	0.21169 (5)	0.0315 (3)
C2A	0.22060 (8)	−0.2062 (3)	0.21258 (7)	0.0255 (3)
O2A	0.21058 (6)	0.1272 (2)	0.11980 (5)	0.0324 (3)
C7	0.48896 (9)	1.0686 (3)	0.03151 (7)	0.0263 (3)
H2AA	0.2086 (11)	−0.355 (4)	0.1785 (10)	0.039 (4)*
H6	0.5110 (10)	0.432 (3)	0.2105 (9)	0.028 (4)*
H2AB	0.1643 (11)	−0.145 (4)	0.2142 (9)	0.038 (4)*
H2	0.2810 (10)	0.532 (3)	0.0692 (9)	0.027 (4)*
H3	0.3308 (10)	0.878 (3)	0.0079 (9)	0.030 (4)*
H7A	0.5416 (11)	1.149 (4)	0.0654 (10)	0.035 (4)*
H5	0.5692 (9)	0.763 (3)	0.1516 (8)	0.029 (4)*
H7B	0.4458 (11)	1.210 (4)	0.0104 (9)	0.038 (4)*
H1A	0.3542 (14)	0.236 (5)	0.1830 (13)	0.074 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0260 (6)	0.0261 (6)	0.0247 (6)	−0.0036 (4)	0.0102 (4)	0.0021 (4)
C2	0.0211 (6)	0.0329 (7)	0.0289 (7)	−0.0024 (5)	0.0083 (5)	0.0033 (5)
C3	0.0239 (6)	0.0323 (7)	0.0252 (7)	0.0012 (5)	0.0063 (5)	0.0058 (5)
C4	0.0273 (6)	0.0217 (6)	0.0234 (6)	−0.0024 (5)	0.0130 (5)	−0.0018 (5)
C5	0.0218 (6)	0.0275 (7)	0.0270 (7)	−0.0040 (5)	0.0079 (5)	−0.0016 (5)
C6	0.0255 (6)	0.0270 (7)	0.0232 (6)	−0.0016 (5)	0.0061 (5)	0.0030 (5)
C1A	0.0229 (6)	0.0222 (6)	0.0236 (6)	−0.0009 (5)	0.0082 (5)	−0.0005 (5)
O1A	0.0248 (5)	0.0368 (6)	0.0289 (5)	−0.0103 (4)	0.0032 (4)	0.0100 (4)
C2A	0.0216 (6)	0.0258 (7)	0.0278 (7)	−0.0041 (5)	0.0063 (5)	0.0033 (5)
O2A	0.0276 (5)	0.0356 (6)	0.0300 (5)	−0.0023 (4)	0.0039 (4)	0.0106 (4)
C7	0.0307 (7)	0.0227 (7)	0.0286 (7)	−0.0039 (5)	0.0140 (6)	0.0007 (5)

Geometric parameters (Å, º)

N1—C2	1.3342 (17)	C1A—O1A	1.3106 (15)
N1—C6	1.3375 (16)	C1A—C2A	1.5136 (17)
C2—C3	1.3821 (18)	C1A—O2A	1.2123 (16)
C2—H2	0.985 (15)	O1A—H1A	1.02 (3)
C3—C4	1.3902 (18)	C2A—C2A^i	1.518 (2)
C3—H3	0.946 (17)	C2A—H2AA	0.957 (19)
C4—C5	1.3876 (18)	C2A—H2AB	0.992 (17)
C4—C7	1.5055 (17)	C7—C7^ii	1.537 (2)
C5—C6	1.3824 (18)	C7—H7A	0.985 (18)
C5—H5	0.968 (15)	C7—H7B	0.981 (18)
C6—H6	0.966 (16)
C2—N1—C6	117.90 (11)	O1A—C1A—C2A	114.32 (11)
N1—C2—C3	122.86 (11)	O2A—C1A—O1A	123.88 (11)
N1—C2—H2	116.6 (10)	O2A—C1A—C2A	121.79 (11)
C3—C2—H2	120.6 (9)	C1A—O1A—H1A	111.1 (12)
C2—C3—C4	119.43 (12)	C1A—C2A—C2A^i	115.27 (13)
C2—C3—H3	120.5 (9)	C1A—C2A—H2AA	105.6 (11)
C4—C3—H3	120.1 (9)	C1A—C2A—H2AB	106.7 (10)
C3—C4—C7	120.97 (12)	C2A^i—C2A—H2AA	111.4 (11)
C5—C4—C3	117.55 (11)	C2A^i—C2A—H2AB	111.9 (10)
C5—C4—C7	121.44 (11)	H2AA—C2A—H2AB	105.4 (14)
C4—C5—H5	121.1 (10)	C4—C7—C7^ii	110.52 (13)
C6—C5—C4	119.44 (11)	C4—C7—H7A	108.7 (10)
C6—C5—H5	119.4 (9)	C4—C7—H7B	110.1 (10)
N1—C6—C5	122.82 (12)	C7^ii—C7—H7A	108.0 (10)
N1—C6—H6	116.0 (9)	C7^ii—C7—H7B	108.0 (10)
C5—C6—H6	121.2 (9)	H7A—C7—H7B	111.5 (14)
N1—C2—C3—C4	0.8 (2)	C4—C5—C6—N1	0.5 (2)
C2—N1—C6—C5	0.11 (19)	C5—C4—C7—C7^ii	92.74 (17)
C2—C3—C4—C5	−0.16 (19)	C6—N1—C2—C3	−0.7 (2)
C2—C3—C4—C7	177.63 (12)	O1A—C1A—C2A—C2A^i	7.0 (2)
C3—C4—C5—C6	−0.43 (19)	O2A—C1A—C2A—C2A^i	−173.53 (14)
C3—C4—C7—C7^ii	−84.96 (18)	C7—C4—C5—C6	−178.20 (11)

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

1,2-bis(4,4'-pyridyl)ethane succinic acid (ETYSUC_180K_B)

Crystal data

C12H12N2·C4H6O4	F(000) = 640
Mr = 302.32	Dx = 1.355 Mg m^−3
Monoclinic, I2/a	Cu Kα radiation, λ = 1.54184 Å
a = 16.6256 (3) Å	Cell parameters from 2502 reflections
b = 4.8792 (1) Å	θ = 4.3–71.4°
c = 19.3393 (4) Å	µ = 0.81 mm^−1
β = 109.164 (2)°	T = 180 K
V = 1481.86 (5) Å^3	Plate, colourless
Z = 4	0.47 × 0.41 × 0.12 mm

Data collection

New Xcalibur, EosS2 diffractometer	1413 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Cu) X-ray Source	1286 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
Detector resolution: 8.0294 pixels mm^-1	θmax = 71.3°, θmin = 4.8°
ω scans	h = −19→20
Absorption correction: gaussian CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −5→5
Tmin = 0.764, Tmax = 0.922	l = −23→23
4217 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.044	All H-atom parameters refined
wR(F^2) = 0.123	w = 1/[σ^2(Fo^2) + (0.0835P)^2 + 0.4509P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
1413 reflections	Δρmax = 0.19 e Å^−3
136 parameters	Δρmin = −0.30 e Å^−3

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
N1	0.39267 (7)	0.4615 (2)	0.14508 (6)	0.0254 (3)
C2	0.34137 (8)	0.5878 (3)	0.08577 (7)	0.0281 (3)
C3	0.36959 (8)	0.7871 (3)	0.04852 (7)	0.0280 (3)
C4	0.45525 (8)	0.8601 (3)	0.07246 (7)	0.0232 (3)
C5	0.50855 (8)	0.7267 (3)	0.13374 (7)	0.0260 (3)
C6	0.47519 (8)	0.5315 (3)	0.16837 (7)	0.0261 (3)
C1A	0.25405 (7)	0.0221 (3)	0.17654 (7)	0.0230 (3)
O1A	0.33328 (6)	0.0920 (2)	0.21165 (5)	0.0319 (3)
C2A	0.22071 (8)	−0.2063 (3)	0.21262 (7)	0.0260 (3)
O2A	0.21061 (6)	0.1272 (2)	0.11985 (5)	0.0330 (3)
C7	0.48890 (9)	1.0683 (3)	0.03147 (7)	0.0267 (3)
H2AA	0.2094 (11)	−0.357 (4)	0.1793 (10)	0.041 (5)*
H6	0.5106 (10)	0.437 (3)	0.2100 (8)	0.028 (4)*
H2	0.2807 (10)	0.528 (4)	0.0683 (9)	0.033 (4)*
H2AB	0.1643 (11)	−0.142 (4)	0.2146 (9)	0.039 (4)*
H3	0.3301 (10)	0.878 (3)	0.0079 (9)	0.031 (4)*
H7A	0.5414 (11)	1.149 (3)	0.0650 (10)	0.032 (4)*
H5	0.5697 (9)	0.763 (3)	0.1521 (8)	0.029 (4)*
H7B	0.4463 (11)	1.211 (4)	0.0112 (9)	0.039 (4)*
H1A	0.3547 (14)	0.236 (5)	0.1830 (12)	0.072 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0256 (6)	0.0267 (6)	0.0249 (6)	−0.0034 (4)	0.0098 (4)	0.0023 (4)
C2	0.0212 (6)	0.0332 (8)	0.0300 (7)	−0.0026 (5)	0.0086 (5)	0.0037 (5)
C3	0.0241 (6)	0.0333 (7)	0.0255 (7)	0.0007 (5)	0.0068 (5)	0.0062 (5)
C4	0.0271 (6)	0.0218 (7)	0.0240 (6)	−0.0018 (5)	0.0127 (5)	−0.0015 (5)
C5	0.0226 (6)	0.0278 (7)	0.0275 (7)	−0.0041 (5)	0.0081 (5)	−0.0008 (5)
C6	0.0254 (6)	0.0275 (7)	0.0233 (6)	−0.0019 (5)	0.0051 (5)	0.0032 (5)
C1A	0.0231 (6)	0.0225 (6)	0.0238 (6)	−0.0012 (5)	0.0082 (5)	0.0000 (5)
O1A	0.0253 (5)	0.0370 (6)	0.0292 (5)	−0.0105 (4)	0.0033 (4)	0.0103 (4)
C2A	0.0225 (6)	0.0256 (7)	0.0288 (7)	−0.0044 (5)	0.0067 (5)	0.0036 (5)
O2A	0.0277 (5)	0.0364 (6)	0.0308 (6)	−0.0029 (4)	0.0040 (4)	0.0111 (4)
C7	0.0317 (7)	0.0228 (7)	0.0289 (7)	−0.0039 (5)	0.0145 (6)	0.0009 (5)

Geometric parameters (Å, º)

N1—C2	1.3345 (17)	C1A—O1A	1.3134 (15)
N1—C6	1.3401 (16)	C1A—C2A	1.5132 (17)
C2—C3	1.3807 (18)	C1A—O2A	1.2112 (16)
C2—H2	0.997 (16)	O1A—H1A	1.03 (3)
C3—C4	1.3915 (18)	C2A—C2A^i	1.515 (2)
C3—H3	0.951 (17)	C2A—H2AA	0.955 (19)
C4—C5	1.3869 (18)	C2A—H2AB	1.001 (17)
C4—C7	1.5050 (17)	C7—C7^ii	1.535 (3)
C5—C6	1.3811 (18)	C7—H7A	0.983 (17)
C5—H5	0.977 (15)	C7—H7B	0.979 (19)
C6—H6	0.945 (16)
C2—N1—C6	117.78 (11)	O1A—C1A—C2A	114.19 (11)
N1—C2—C3	122.88 (11)	O2A—C1A—O1A	123.84 (11)
N1—C2—H2	116.6 (10)	O2A—C1A—C2A	121.97 (11)
C3—C2—H2	120.5 (10)	C1A—O1A—H1A	111.4 (12)
C2—C3—C4	119.50 (12)	C1A—C2A—C2A^i	115.42 (13)
C2—C3—H3	119.8 (9)	C1A—C2A—H2AA	106.1 (11)
C4—C3—H3	120.6 (10)	C1A—C2A—H2AB	106.0 (10)
C3—C4—C7	120.94 (12)	C2A^i—C2A—H2AA	110.4 (11)
C5—C4—C3	117.48 (11)	C2A^i—C2A—H2AB	111.7 (10)
C5—C4—C7	121.54 (11)	H2AA—C2A—H2AB	106.7 (14)
C4—C5—H5	121.5 (9)	C4—C7—C7^ii	110.62 (13)
C6—C5—C4	119.49 (11)	C4—C7—H7A	109.0 (10)
C6—C5—H5	119.0 (9)	C4—C7—H7B	110.3 (10)
N1—C6—C5	122.86 (12)	C7^ii—C7—H7A	107.8 (10)
N1—C6—H6	116.4 (9)	C7^ii—C7—H7B	108.8 (10)
C5—C6—H6	120.7 (9)	H7A—C7—H7B	110.2 (14)
N1—C2—C3—C4	0.8 (2)	C4—C5—C6—N1	0.5 (2)
C2—N1—C6—C5	0.01 (19)	C5—C4—C7—C7^ii	92.66 (17)
C2—C3—C4—C5	−0.20 (19)	C6—N1—C2—C3	−0.7 (2)
C2—C3—C4—C7	177.56 (12)	O1A—C1A—C2A—C2A^i	7.2 (2)
C3—C4—C5—C6	−0.42 (19)	O2A—C1A—C2A—C2A^i	−173.40 (14)
C3—C4—C7—C7^ii	−85.01 (18)	C7—C4—C5—C6	−178.17 (11)

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

1,2-bis(4,4'-pyridyl)ethane succinic acid (ETYSUC_185K_B)

Crystal data

C12H12N2·C4H6O4	F(000) = 640
Mr = 302.32	Dx = 1.354 Mg m^−3
Monoclinic, I2/a	Cu Kα radiation, λ = 1.54184 Å
a = 16.6268 (3) Å	Cell parameters from 2486 reflections
b = 4.8810 (1) Å	θ = 4.3–71.3°
c = 19.3397 (4) Å	µ = 0.81 mm^−1
β = 109.141 (2)°	T = 185 K
V = 1482.75 (5) Å^3	Plate, colourless
Z = 4	0.47 × 0.41 × 0.12 mm

Data collection

New Xcalibur, EosS2 diffractometer	1414 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Cu) X-ray Source	1300 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
Detector resolution: 8.0294 pixels mm^-1	θmax = 71.4°, θmin = 4.8°
ω scans	h = −19→20
Absorption correction: gaussian CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −5→5
Tmin = 0.764, Tmax = 0.922	l = −23→23
4221 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.043	All H-atom parameters refined
wR(F^2) = 0.121	w = 1/[σ^2(Fo^2) + (0.0816P)^2 + 0.4553P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
1414 reflections	Δρmax = 0.19 e Å^−3
136 parameters	Δρmin = −0.29 e Å^−3

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
N1	0.39275 (7)	0.4616 (2)	0.14508 (6)	0.0261 (3)
C2	0.34140 (8)	0.5875 (3)	0.08572 (7)	0.0290 (3)
C3	0.36958 (8)	0.7870 (3)	0.04841 (7)	0.0288 (3)
C4	0.45518 (8)	0.8597 (3)	0.07240 (6)	0.0240 (3)
C5	0.50858 (8)	0.7268 (3)	0.13374 (7)	0.0265 (3)
C6	0.47516 (8)	0.5313 (3)	0.16839 (7)	0.0267 (3)
C1A	0.25411 (7)	0.0223 (2)	0.17656 (7)	0.0237 (3)
O1A	0.33320 (6)	0.0916 (2)	0.21161 (5)	0.0328 (3)
C2A	0.22064 (8)	−0.2062 (3)	0.21264 (7)	0.0269 (3)
O2A	0.21071 (6)	0.1270 (2)	0.11987 (5)	0.0341 (3)
C7	0.48894 (9)	1.0682 (3)	0.03150 (7)	0.0274 (3)
H2AA	0.2088 (11)	−0.356 (4)	0.1794 (10)	0.041 (4)*
H2AB	0.1655 (11)	−0.141 (4)	0.2152 (9)	0.042 (5)*
H3	0.3298 (10)	0.876 (3)	0.0071 (9)	0.032 (4)*
H6	0.5118 (10)	0.437 (4)	0.2113 (9)	0.036 (4)*
H2	0.2809 (10)	0.529 (3)	0.0689 (9)	0.031 (4)*
H7A	0.5408 (11)	1.147 (4)	0.0646 (10)	0.037 (4)*
H5	0.5694 (9)	0.761 (3)	0.1521 (8)	0.030 (4)*
H7B	0.4465 (11)	1.210 (4)	0.0107 (10)	0.043 (4)*
H1A	0.3539 (14)	0.233 (5)	0.1818 (12)	0.070 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0265 (6)	0.0277 (6)	0.0253 (6)	−0.0040 (4)	0.0103 (4)	0.0019 (4)
C2	0.0223 (6)	0.0347 (8)	0.0301 (7)	−0.0026 (5)	0.0087 (5)	0.0043 (5)
C3	0.0250 (6)	0.0339 (7)	0.0265 (7)	0.0010 (5)	0.0072 (5)	0.0065 (5)
C4	0.0285 (6)	0.0229 (6)	0.0237 (6)	−0.0026 (5)	0.0130 (5)	−0.0024 (5)
C5	0.0230 (6)	0.0286 (7)	0.0277 (7)	−0.0045 (5)	0.0080 (5)	−0.0016 (5)
C6	0.0264 (6)	0.0281 (7)	0.0237 (6)	−0.0022 (5)	0.0057 (5)	0.0026 (5)
C1A	0.0238 (6)	0.0235 (6)	0.0240 (6)	−0.0008 (5)	0.0079 (5)	−0.0004 (5)
O1A	0.0261 (5)	0.0384 (6)	0.0296 (5)	−0.0105 (4)	0.0033 (4)	0.0105 (4)
C2A	0.0231 (6)	0.0267 (7)	0.0294 (7)	−0.0044 (5)	0.0068 (5)	0.0033 (5)
O2A	0.0292 (5)	0.0378 (6)	0.0312 (6)	−0.0027 (4)	0.0042 (4)	0.0114 (4)
C7	0.0325 (7)	0.0238 (7)	0.0291 (7)	−0.0040 (5)	0.0145 (6)	0.0005 (5)

Geometric parameters (Å, º)

N1—C2	1.3349 (17)	C1A—O1A	1.3110 (15)
N1—C6	1.3385 (16)	C1A—C2A	1.5146 (17)
C2—C3	1.3820 (18)	C1A—O2A	1.2106 (15)
C2—H2	0.993 (15)	O1A—H1A	1.03 (2)
C3—C4	1.3907 (18)	C2A—C2A^i	1.516 (2)
C3—H3	0.957 (17)	C2A—H2AA	0.952 (19)
C4—C5	1.3878 (18)	C2A—H2AB	0.986 (17)
C4—C7	1.5058 (17)	C7—C7^ii	1.535 (3)
C5—C6	1.3829 (18)	C7—H7A	0.969 (18)
C5—H5	0.970 (14)	C7—H7B	0.978 (19)
C6—H6	0.970 (17)
C2—N1—C6	117.90 (11)	O1A—C1A—C2A	114.19 (11)
N1—C2—C3	122.87 (11)	O2A—C1A—O1A	123.92 (11)
N1—C2—H2	116.3 (10)	O2A—C1A—C2A	121.89 (11)
C3—C2—H2	120.8 (10)	C1A—O1A—H1A	110.3 (12)
C2—C3—C4	119.39 (12)	C1A—C2A—C2A^i	115.32 (13)
C2—C3—H3	119.7 (9)	C1A—C2A—H2AA	106.4 (11)
C4—C3—H3	120.9 (9)	C1A—C2A—H2AB	105.9 (11)
C3—C4—C7	120.95 (12)	C2A^i—C2A—H2AA	110.6 (11)
C5—C4—C3	117.62 (11)	C2A^i—C2A—H2AB	111.2 (10)
C5—C4—C7	121.39 (11)	H2AA—C2A—H2AB	106.9 (14)
C4—C5—H5	122.0 (9)	C4—C7—C7^ii	110.56 (13)
C6—C5—C4	119.39 (11)	C4—C7—H7A	109.0 (10)
C6—C5—H5	118.5 (9)	C4—C7—H7B	110.6 (10)
N1—C6—C5	122.81 (12)	C7^ii—C7—H7A	107.7 (10)
N1—C6—H6	117.0 (10)	C7^ii—C7—H7B	108.1 (11)
C5—C6—H6	120.2 (10)	H7A—C7—H7B	110.8 (14)
N1—C2—C3—C4	0.9 (2)	C4—C5—C6—N1	0.4 (2)
C2—N1—C6—C5	0.10 (19)	C5—C4—C7—C7^ii	92.87 (17)
C2—C3—C4—C5	−0.27 (19)	C6—N1—C2—C3	−0.8 (2)
C2—C3—C4—C7	177.62 (12)	O1A—C1A—C2A—C2A^i	7.1 (2)
C3—C4—C5—C6	−0.34 (19)	O2A—C1A—C2A—C2A^i	−173.59 (14)
C3—C4—C7—C7^ii	−84.94 (18)	C7—C4—C5—C6	−178.22 (11)

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

1,2-bis(4,4'-pyridyl)ethane succinic acid (ETYSUC_190K_B)

Crystal data

C12H12N2·C4H6O4	F(000) = 640
Mr = 302.32	Dx = 1.353 Mg m^−3
Monoclinic, I2/a	Cu Kα radiation, λ = 1.54184 Å
a = 16.6279 (3) Å	Cell parameters from 2456 reflections
b = 4.8825 (1) Å	θ = 4.3–71.4°
c = 19.3411 (4) Å	µ = 0.81 mm^−1
β = 109.105 (2)°	T = 190 K
V = 1483.73 (5) Å^3	Plate, colourless
Z = 4	0.44 × 0.42 × 0.15 mm

Data collection

New Xcalibur, EosS2 diffractometer	1415 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Cu) X-ray Source	1295 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
Detector resolution: 8.0294 pixels mm^-1	θmax = 71.4°, θmin = 4.8°
ω scans	h = −19→20
Absorption correction: gaussian CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −5→5
Tmin = 0.764, Tmax = 0.904	l = −23→23
4224 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.044	All H-atom parameters refined
wR(F^2) = 0.124	w = 1/[σ^2(Fo^2) + (0.0847P)^2 + 0.3322P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
1415 reflections	Δρmax = 0.18 e Å^−3
136 parameters	Δρmin = −0.29 e Å^−3

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
N1	0.39280 (7)	0.4613 (2)	0.14505 (6)	0.0269 (3)
C2	0.34156 (8)	0.5870 (3)	0.08574 (7)	0.0294 (3)
C3	0.36960 (8)	0.7862 (3)	0.04838 (7)	0.0293 (3)
C4	0.45525 (8)	0.8595 (3)	0.07243 (6)	0.0245 (3)
C5	0.50855 (8)	0.7268 (3)	0.13368 (7)	0.0272 (3)
C6	0.47514 (8)	0.5314 (3)	0.16839 (7)	0.0274 (3)
C1A	0.25426 (7)	0.0221 (2)	0.17664 (6)	0.0241 (3)
O1A	0.33328 (6)	0.0914 (2)	0.21161 (5)	0.0333 (3)
C2A	0.22072 (8)	−0.2061 (3)	0.21271 (7)	0.0272 (3)
O2A	0.21078 (6)	0.1270 (2)	0.11995 (5)	0.0347 (3)
C7	0.48893 (9)	1.0681 (3)	0.03147 (7)	0.0277 (3)
H6	0.5114 (10)	0.438 (3)	0.2106 (9)	0.033 (4)*
H3	0.3297 (10)	0.875 (3)	0.0070 (9)	0.035 (4)*
H2	0.2809 (10)	0.529 (3)	0.0682 (9)	0.032 (4)*
H2AA	0.2099 (11)	−0.358 (4)	0.1791 (10)	0.044 (5)*
H2AB	0.1653 (10)	−0.147 (4)	0.2141 (9)	0.039 (4)*
H7A	0.5414 (10)	1.151 (3)	0.0651 (9)	0.035 (4)*
H5	0.5698 (9)	0.763 (3)	0.1523 (8)	0.031 (4)*
H7B	0.4466 (12)	1.209 (4)	0.0112 (10)	0.047 (5)*
H1A	0.3527 (14)	0.235 (5)	0.1821 (12)	0.078 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0273 (6)	0.0284 (6)	0.0264 (6)	−0.0039 (4)	0.0108 (4)	0.0024 (4)
C2	0.0220 (6)	0.0349 (8)	0.0315 (7)	−0.0028 (5)	0.0091 (5)	0.0041 (5)
C3	0.0250 (6)	0.0348 (7)	0.0271 (7)	0.0011 (5)	0.0072 (5)	0.0065 (5)
C4	0.0287 (6)	0.0237 (6)	0.0246 (6)	−0.0025 (5)	0.0137 (5)	−0.0018 (5)
C5	0.0236 (6)	0.0297 (7)	0.0284 (7)	−0.0047 (5)	0.0085 (5)	−0.0010 (5)
C6	0.0270 (6)	0.0292 (7)	0.0241 (6)	−0.0017 (5)	0.0061 (5)	0.0034 (5)
C1A	0.0242 (6)	0.0242 (6)	0.0241 (6)	−0.0008 (5)	0.0082 (5)	0.0001 (5)
O1A	0.0265 (5)	0.0388 (6)	0.0303 (5)	−0.0109 (4)	0.0035 (4)	0.0107 (4)
C2A	0.0234 (6)	0.0272 (7)	0.0302 (7)	−0.0041 (5)	0.0076 (5)	0.0033 (5)
O2A	0.0291 (5)	0.0384 (6)	0.0321 (6)	−0.0024 (4)	0.0040 (4)	0.0119 (4)
C7	0.0333 (7)	0.0235 (7)	0.0298 (7)	−0.0042 (5)	0.0152 (6)	0.0006 (5)

Geometric parameters (Å, º)

N1—C2	1.3337 (17)	C1A—O1A	1.3103 (15)
N1—C6	1.3383 (16)	C1A—C2A	1.5146 (17)
C2—C3	1.3807 (18)	C1A—O2A	1.2117 (15)
C2—H2	0.995 (15)	O1A—H1A	1.02 (3)
C3—C4	1.3925 (17)	C2A—C2A^i	1.514 (2)
C3—H3	0.960 (17)	C2A—H2AA	0.965 (19)
C4—C5	1.3860 (18)	C2A—H2AB	0.974 (17)
C4—C7	1.5065 (16)	C7—C7^ii	1.534 (2)
C5—C6	1.3834 (18)	C7—H7A	0.987 (17)
C5—H5	0.978 (14)	C7—H7B	0.97 (2)
C6—H6	0.957 (16)
C2—N1—C6	117.86 (11)	O1A—C1A—C2A	114.23 (10)
N1—C2—C3	122.98 (11)	O2A—C1A—O1A	123.94 (11)
N1—C2—H2	117.0 (10)	O2A—C1A—C2A	121.82 (11)
C3—C2—H2	120.0 (10)	C1A—O1A—H1A	109.7 (12)
C2—C3—C4	119.32 (12)	C1A—C2A—H2AA	105.8 (11)
C2—C3—H3	119.7 (10)	C1A—C2A—H2AB	106.7 (10)
C4—C3—H3	120.9 (10)	C2A^i—C2A—C1A	115.34 (13)
C3—C4—C7	120.90 (11)	C2A^i—C2A—H2AA	110.1 (11)
C5—C4—C3	117.61 (11)	C2A^i—C2A—H2AB	112.2 (10)
C5—C4—C7	121.45 (11)	H2AA—C2A—H2AB	106.1 (14)
C4—C5—H5	121.9 (9)	C4—C7—C7^ii	110.56 (13)
C6—C5—C4	119.41 (11)	C4—C7—H7A	109.3 (10)
C6—C5—H5	118.7 (9)	C4—C7—H7B	110.3 (11)
N1—C6—C5	122.81 (12)	C7^ii—C7—H7A	108.1 (10)
N1—C6—H6	117.1 (9)	C7^ii—C7—H7B	108.5 (11)
C5—C6—H6	120.1 (9)	H7A—C7—H7B	110.1 (14)
N1—C2—C3—C4	0.8 (2)	C4—C5—C6—N1	0.6 (2)
C2—N1—C6—C5	−0.01 (19)	C5—C4—C7—C7^ii	92.87 (17)
C2—C3—C4—C5	−0.19 (19)	C6—N1—C2—C3	−0.7 (2)
C2—C3—C4—C7	177.63 (12)	O1A—C1A—C2A—C2A^i	7.0 (2)
C3—C4—C5—C6	−0.47 (19)	O2A—C1A—C2A—C2A^i	−173.53 (14)
C3—C4—C7—C7^ii	−84.87 (18)	C7—C4—C5—C6	−178.28 (11)

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

4,4'-Ethane-1,2-diyldipyridine succinic acid (ETYSUC_193)

Crystal data

C12H12N2·C4H6O4	F(000) = 640
Mr = 302.32	Dx = 1.513 Mg m^−3
Monoclinic, I2/a	Mo Kα radiation, λ = 0.71073 Å
a = 16.53 (2) Å	Cell parameters from 735 reflections
b = 4.5612 (3) Å	θ = 4.4–22.2°
c = 19.065 (7) Å	µ = 0.11 mm^−1
β = 112.63 (10)°	T = 295 K
V = 1327 (2) Å^3	Plate, colourless
Z = 4	0.35 × 0.16 × 0.03 mm

Data collection

Xcalibur, Eos diffractometer	292 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	159 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.087
Detector resolution: 16.1544 pixels mm^-1	θmax = 26.1°, θmin = 4.4°
ω scans	h = −6→6
Absorption correction: gaussian CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022) Numerical absorption correction based on gaussian integration over a multifaceted crystal model (Absorb Angel (2004) J. Appl. Cryst. 37:486-492)	k = −5→5
Tmin = 0.996, Tmax = 0.996	l = −21→22
1144 measured reflections

Refinement

Refinement on F^2	Primary atom site location: iterative
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.089	H-atom parameters constrained
wR(F^2) = 0.291	w = 1/[σ^2(Fo^2) + (0.1697P)^2 + 2.2082P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
292 reflections	Δρmax = 0.26 e Å^−3
46 parameters	Δρmin = −0.27 e Å^−3
8 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
N1	0.3929 (18)	0.470 (2)	0.1460 (7)	0.037 (4)*
C2	0.3382 (18)	0.617 (2)	0.0870 (7)	0.042 (4)*
H2	0.2783	0.5816	0.0707	0.050*
C3	0.3685 (18)	0.825 (2)	0.0486 (9)	0.037 (5)*
H3	0.3293	0.9254	0.0069	0.044*
C4	0.4586 (17)	0.879 (2)	0.0740 (7)	0.022 (4)*
C5	0.5141 (17)	0.727 (2)	0.1351 (6)	0.035 (4)*
H5	0.5742	0.7572	0.1528	0.042*
C6	0.4793 (19)	0.524 (2)	0.1708 (9)	0.029 (4)*
H6	0.5172	0.4238	0.2131	0.035*
C1A	0.2532 (16)	0.032 (2)	0.1765 (7)	0.023 (4)*
O1A	0.3355 (16)	0.0994 (18)	0.2119 (6)	0.048 (3)*
H1A	0.3505	0.2131	0.1858	0.073*
C2A	0.217 (2)	−0.201 (2)	0.2116 (7)	0.033 (3)*
H2AA	0.2004	−0.3693	0.1778	0.040*
H2AB	0.1651	−0.1282	0.2173	0.040*
O2A	0.2068 (16)	0.1499 (14)	0.1155 (5)	0.040 (3)*
C7	0.491 (2)	1.084 (2)	0.0307 (8)	0.033 (3)*
H7A	0.5437	1.1789	0.0647	0.040*
H7B	0.4469	1.2339	0.0075	0.040*

Geometric parameters (Å, º)

N1—C2	1.323 (17)	C1A—O1A	1.30 (2)
N1—C6	1.34 (2)	C1A—C2A	1.50 (2)
C2—H2	0.9300	C1A—O2A	1.243 (15)
C2—C3	1.405 (16)	O1A—H1A	0.8200
C3—H3	0.9300	C2A—C2A^i	1.51 (4)
C3—C4	1.40 (2)	C2A—H2AA	0.9700
C4—C5	1.364 (17)	C2A—H2AB	0.9700
C4—C7	1.47 (2)	C7—C7^ii	1.53 (3)
C5—H5	0.9300	C7—H7A	0.9700
C5—C6	1.394 (16)	C7—H7B	0.9700
C6—H6	0.9300
C2—N1—C6	119.5 (17)	O1A—C1A—C2A	116.8 (15)
N1—C2—H2	119.3	O2A—C1A—O1A	122.0 (17)
N1—C2—C3	121 (2)	O2A—C1A—C2A	121 (2)
C3—C2—H2	119.3	C1A—O1A—H1A	109.5
C2—C3—H3	120.5	C1A—C2A—C2A^i	112 (3)
C4—C3—C2	118.9 (18)	C1A—C2A—H2AA	109.1
C4—C3—H3	120.5	C1A—C2A—H2AB	109.1
C3—C4—C7	118.8 (16)	C2A^i—C2A—H2AA	109.1
C5—C4—C3	118.9 (17)	C2A^i—C2A—H2AB	109.1
C5—C4—C7	122 (2)	H2AA—C2A—H2AB	107.9
C4—C5—H5	120.5	C4—C7—C7^ii	109.7 (11)
C4—C5—C6	119 (2)	C4—C7—H7A	109.7
C6—C5—H5	120.5	C4—C7—H7B	109.7
N1—C6—C5	122.2 (17)	C7^ii—C7—H7A	109.7
N1—C6—H6	118.9	C7^ii—C7—H7B	109.7
C5—C6—H6	118.9	H7A—C7—H7B	108.2
N1—C2—C3—C4	−0.7 (19)	C4—C5—C6—N1	1.4 (19)
C2—N1—C6—C5	−2 (2)	C5—C4—C7—C7^ii	87 (3)
C2—C3—C4—C5	0 (2)	C6—N1—C2—C3	1 (2)
C2—C3—C4—C7	176.2 (9)	O1A—C1A—C2A—C2A^i	6 (2)
C3—C4—C5—C6	−0.7 (18)	O2A—C1A—C2A—C2A^i	−175.9 (16)
C3—C4—C7—C7^ii	−89 (3)	C7—C4—C5—C6	−176.4 (10)

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

1,2-bis(4,4'-pyridyl)ethane succinic acid (ETYSUC_200K_B)

Crystal data

C12H12N2·C4H6O4	F(000) = 640
Mr = 302.32	Dx = 1.351 Mg m^−3
Monoclinic, I2/a	Cu Kα radiation, λ = 1.54184 Å
a = 16.6313 (5) Å	Cell parameters from 2436 reflections
b = 4.8871 (1) Å	θ = 4.3–71.2°
c = 19.3441 (6) Å	µ = 0.81 mm^−1
β = 109.050 (3)°	T = 200 K
V = 1486.16 (8) Å^3	Plate, colourless
Z = 4	0.47 × 0.41 × 0.12 mm

Data collection

New Xcalibur, EosS2 diffractometer	1415 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Cu) X-ray Source	1283 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
Detector resolution: 8.0294 pixels mm^-1	θmax = 71.4°, θmin = 4.8°
ω scans	h = −19→20
Absorption correction: gaussian CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −5→5
Tmin = 0.765, Tmax = 0.923	l = −23→23
4155 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.044	All H-atom parameters refined
wR(F^2) = 0.125	w = 1/[σ^2(Fo^2) + (0.0832P)^2 + 0.3962P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
1415 reflections	Δρmax = 0.19 e Å^−3
136 parameters	Δρmin = −0.27 e Å^−3

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
N1	0.39283 (7)	0.4609 (2)	0.14504 (6)	0.0277 (3)
C2	0.34173 (8)	0.5861 (3)	0.08575 (7)	0.0309 (3)
C3	0.36980 (8)	0.7854 (3)	0.04834 (7)	0.0301 (3)
C4	0.45519 (8)	0.8592 (3)	0.07240 (7)	0.0251 (3)
C5	0.50841 (8)	0.7268 (3)	0.13365 (7)	0.0280 (3)
C6	0.47520 (8)	0.5314 (3)	0.16830 (7)	0.0282 (3)
C1A	0.25425 (8)	0.0218 (3)	0.17665 (7)	0.0248 (3)
O1A	0.33335 (6)	0.0907 (2)	0.21154 (5)	0.0347 (3)
C2A	0.22084 (8)	−0.2064 (3)	0.21272 (7)	0.0284 (3)
O2A	0.21097 (6)	0.1266 (2)	0.11999 (5)	0.0361 (3)
C7	0.48890 (9)	1.0677 (3)	0.03143 (7)	0.0287 (3)
H2AA	0.2094 (12)	−0.358 (4)	0.1793 (10)	0.049 (5)*
H3	0.3306 (10)	0.874 (4)	0.0080 (9)	0.035 (4)*
H6	0.5103 (10)	0.439 (3)	0.2107 (9)	0.031 (4)*
H2AB	0.1652 (11)	−0.144 (4)	0.2146 (9)	0.045 (5)*
H2	0.2804 (10)	0.528 (4)	0.0686 (9)	0.035 (4)*
H5	0.5689 (10)	0.761 (4)	0.1519 (8)	0.034 (4)*
H7A	0.5397 (11)	1.152 (4)	0.0648 (10)	0.040 (4)*
H7B	0.4454 (12)	1.208 (4)	0.0105 (10)	0.047 (5)*
H1A	0.3525 (15)	0.231 (6)	0.1816 (13)	0.082 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0281 (6)	0.0292 (6)	0.0271 (6)	−0.0042 (4)	0.0109 (5)	0.0024 (4)
C2	0.0233 (6)	0.0365 (8)	0.0325 (7)	−0.0031 (5)	0.0086 (5)	0.0047 (5)
C3	0.0262 (6)	0.0351 (8)	0.0279 (7)	0.0012 (5)	0.0075 (5)	0.0071 (5)
C4	0.0301 (6)	0.0238 (7)	0.0251 (6)	−0.0029 (5)	0.0139 (5)	−0.0016 (5)
C5	0.0237 (6)	0.0304 (7)	0.0296 (7)	−0.0051 (5)	0.0083 (5)	−0.0012 (5)
C6	0.0271 (7)	0.0301 (7)	0.0249 (6)	−0.0013 (5)	0.0053 (5)	0.0041 (5)
C1A	0.0248 (6)	0.0241 (7)	0.0255 (6)	−0.0009 (5)	0.0081 (5)	−0.0003 (5)
O1A	0.0273 (5)	0.0408 (6)	0.0315 (5)	−0.0110 (4)	0.0033 (4)	0.0116 (4)
C2A	0.0243 (6)	0.0281 (7)	0.0315 (7)	−0.0049 (5)	0.0073 (6)	0.0036 (5)
O2A	0.0303 (5)	0.0400 (6)	0.0333 (6)	−0.0032 (4)	0.0042 (4)	0.0130 (4)
C7	0.0347 (7)	0.0237 (7)	0.0313 (7)	−0.0044 (5)	0.0157 (6)	0.0004 (5)

Geometric parameters (Å, º)

N1—C2	1.3325 (17)	C1A—O1A	1.3115 (15)
N1—C6	1.3400 (16)	C1A—C2A	1.5140 (17)
C2—C3	1.3822 (19)	C1A—O2A	1.2113 (16)
C2—H2	1.005 (16)	O1A—H1A	1.01 (3)
C3—C4	1.3899 (18)	C2A—C2A^i	1.513 (2)
C3—H3	0.943 (17)	C2A—H2AA	0.96 (2)
C4—C5	1.3861 (18)	C2A—H2AB	0.986 (18)
C4—C7	1.5068 (17)	C7—C7^ii	1.532 (3)
C5—C6	1.3813 (18)	C7—H7A	0.972 (19)
C5—H5	0.966 (15)	C7—H7B	0.98 (2)
C6—H6	0.952 (16)
C2—N1—C6	117.76 (11)	O1A—C1A—C2A	114.18 (11)
N1—C2—C3	123.00 (12)	O2A—C1A—O1A	123.84 (11)
N1—C2—H2	116.6 (10)	O2A—C1A—C2A	121.97 (11)
C3—C2—H2	120.4 (10)	C1A—O1A—H1A	109.3 (13)
C2—C3—C4	119.36 (12)	C1A—C2A—H2AA	106.3 (11)
C2—C3—H3	119.7 (10)	C1A—C2A—H2AB	106.2 (11)
C4—C3—H3	120.9 (10)	C2A^i—C2A—C1A	115.41 (13)
C3—C4—C7	120.95 (12)	C2A^i—C2A—H2AA	110.4 (11)
C5—C4—C3	117.56 (12)	C2A^i—C2A—H2AB	111.7 (10)
C5—C4—C7	121.45 (12)	H2AA—C2A—H2AB	106.3 (15)
C4—C5—H5	122.1 (10)	C4—C7—C7^ii	110.67 (13)
C6—C5—C4	119.50 (12)	C4—C7—H7A	109.3 (11)
C6—C5—H5	118.3 (10)	C4—C7—H7B	109.8 (11)
N1—C6—C5	122.80 (12)	C7^ii—C7—H7A	109.1 (11)
N1—C6—H6	116.0 (9)	C7^ii—C7—H7B	108.0 (11)
C5—C6—H6	121.1 (9)	H7A—C7—H7B	110.0 (15)
N1—C2—C3—C4	0.7 (2)	C4—C5—C6—N1	0.4 (2)
C2—N1—C6—C5	0.2 (2)	C5—C4—C7—C7^ii	92.94 (18)
C2—C3—C4—C5	−0.1 (2)	C6—N1—C2—C3	−0.8 (2)
C2—C3—C4—C7	177.63 (12)	O1A—C1A—C2A—C2A^i	7.4 (2)
C3—C4—C5—C6	−0.49 (19)	O2A—C1A—C2A—C2A^i	−173.46 (15)
C3—C4—C7—C7^ii	−84.66 (18)	C7—C4—C5—C6	−178.17 (11)

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

4,4'-Ethane-1,2-diyldipyridine succinic acid (etysuc_200K)

Crystal data

C12H12N2·C4H6O4	F(000) = 640
Mr = 302.32	Dx = 1.350 Mg m^−3
Monoclinic, I2/a	Cu Kα radiation, λ = 1.54184 Å
a = 16.6408 (10) Å	Cell parameters from 966 reflections
b = 4.8878 (3) Å	θ = 4.8–71.1°
c = 19.3501 (10) Å	µ = 0.81 mm^−1
β = 109.048 (6)°	T = 200 K
V = 1487.70 (16) Å^3	Plate, colourless
Z = 4	0.14 × 0.09 × 0.04 mm

Data collection

SuperNova, Single source at offset/far, Atlas diffractometer	1422 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source	953 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.041
Detector resolution: 10.5384 pixels mm^-1	θmax = 72.3°, θmin = 4.8°
ω scans	h = −20→19
Absorption correction: gaussian CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −5→5
Tmin = 0.903, Tmax = 1.000	l = −17→23
2799 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.059	All H-atom parameters refined
wR(F^2) = 0.188	w = 1/[σ^2(Fo^2) + (0.0957P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
1422 reflections	Δρmax = 0.19 e Å^−3
136 parameters	Δρmin = −0.29 e Å^−3

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
N1	0.39276 (14)	0.4598 (5)	0.14495 (11)	0.0422 (6)
C2	0.34167 (19)	0.5868 (7)	0.08572 (15)	0.0468 (7)
C3	0.37015 (19)	0.7855 (7)	0.04835 (14)	0.0455 (8)
C4	0.45518 (18)	0.8590 (6)	0.07235 (13)	0.0398 (7)
C5	0.50852 (19)	0.7266 (7)	0.13358 (14)	0.0438 (7)
C6	0.47532 (19)	0.5308 (7)	0.16831 (14)	0.0455 (7)
C1A	0.25420 (18)	0.0211 (6)	0.17683 (13)	0.0419 (7)
O1A	0.33338 (12)	0.0906 (5)	0.21152 (10)	0.0503 (6)
C2A	0.22086 (18)	−0.2068 (7)	0.21296 (15)	0.0422 (7)
O2A	0.21082 (13)	0.1269 (5)	0.11979 (10)	0.0528 (6)
C7	0.4884 (2)	1.0678 (7)	0.03120 (15)	0.0449 (7)
H1A	0.353 (3)	0.229 (9)	0.184 (2)	0.089 (13)*
H6	0.5077 (18)	0.440 (6)	0.2108 (15)	0.036 (7)*
H2	0.281 (2)	0.522 (6)	0.0666 (15)	0.044 (8)*
H2AA	0.207 (2)	−0.365 (7)	0.1786 (18)	0.057 (9)*
H2AB	0.167 (2)	−0.151 (7)	0.2130 (17)	0.056 (9)*
H3	0.328 (2)	0.886 (7)	0.0045 (18)	0.060 (9)*
H7A	0.541 (2)	1.169 (7)	0.0647 (16)	0.046 (8)*
H5	0.5651 (19)	0.765 (7)	0.1507 (15)	0.047 (8)*
H7B	0.443 (2)	1.210 (9)	0.008 (2)	0.074 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0443 (12)	0.0512 (16)	0.0364 (10)	−0.0029 (11)	0.0205 (9)	0.0038 (11)
C2	0.0447 (15)	0.056 (2)	0.0430 (13)	−0.0053 (15)	0.0191 (12)	0.0029 (13)
C3	0.0470 (15)	0.055 (2)	0.0393 (13)	−0.0023 (14)	0.0205 (12)	0.0054 (13)
C4	0.0505 (15)	0.0411 (17)	0.0366 (12)	−0.0007 (13)	0.0262 (11)	0.0005 (11)
C5	0.0444 (15)	0.0514 (19)	0.0405 (13)	−0.0021 (14)	0.0206 (12)	0.0018 (13)
C6	0.0530 (16)	0.0497 (19)	0.0363 (13)	−0.0036 (14)	0.0181 (12)	0.0056 (13)
C1A	0.0489 (15)	0.0458 (18)	0.0364 (12)	−0.0017 (14)	0.0211 (12)	0.0005 (12)
O1A	0.0457 (11)	0.0616 (15)	0.0435 (10)	−0.0127 (10)	0.0142 (9)	0.0112 (10)
C2A	0.0416 (14)	0.0458 (18)	0.0430 (13)	−0.0039 (13)	0.0187 (12)	0.0035 (13)
O2A	0.0480 (11)	0.0654 (16)	0.0447 (11)	−0.0020 (11)	0.0146 (9)	0.0134 (10)
C7	0.0557 (17)	0.0453 (18)	0.0419 (13)	−0.0060 (15)	0.0273 (13)	0.0021 (13)

Geometric parameters (Å, º)

N1—C2	1.336 (4)	C1A—O1A	1.313 (3)
N1—C6	1.344 (4)	C1A—C2A	1.513 (4)
C2—C3	1.384 (4)	C1A—O2A	1.219 (3)
C2—H2	1.00 (3)	O1A—H1A	0.98 (5)
C3—C4	1.385 (4)	C2A—C2A^i	1.506 (6)
C3—H3	1.03 (3)	C2A—H2AA	1.00 (4)
C4—C5	1.387 (4)	C2A—H2AB	0.94 (3)
C4—C7	1.506 (4)	C7—C7^ii	1.534 (5)
C5—C6	1.384 (4)	C7—H7A	1.03 (3)
C5—H5	0.91 (3)	C7—H7B	1.02 (4)
C6—H6	0.93 (3)
C2—N1—C6	117.6 (2)	O1A—C1A—C2A	114.3 (2)
N1—C2—C3	122.9 (3)	O2A—C1A—O1A	123.5 (3)
N1—C2—H2	116.8 (17)	O2A—C1A—C2A	122.2 (3)
C3—C2—H2	120.1 (17)	C1A—O1A—H1A	111 (2)
C2—C3—C4	119.6 (3)	C1A—C2A—H2AA	107.7 (18)
C2—C3—H3	120.7 (19)	C1A—C2A—H2AB	106 (2)
C4—C3—H3	119.6 (19)	C2A^i—C2A—C1A	115.3 (3)
C3—C4—C5	117.7 (3)	C2A^i—C2A—H2AA	111 (2)
C3—C4—C7	120.6 (3)	C2A^i—C2A—H2AB	113.6 (19)
C5—C4—C7	121.7 (3)	H2AA—C2A—H2AB	102 (3)
C4—C5—H5	120.8 (19)	C4—C7—C7^ii	110.7 (3)
C6—C5—C4	119.5 (3)	C4—C7—H7A	112.1 (17)
C6—C5—H5	120 (2)	C4—C7—H7B	111 (2)
N1—C6—C5	122.8 (3)	C7^ii—C7—H7A	108.9 (17)
N1—C6—H6	114.0 (17)	C7^ii—C7—H7B	107 (2)
C5—C6—H6	123.2 (17)	H7A—C7—H7B	108 (3)
N1—C2—C3—C4	0.1 (5)	C4—C5—C6—N1	0.6 (5)
C2—N1—C6—C5	−0.2 (4)	C5—C4—C7—C7^ii	92.1 (4)
C2—C3—C4—C5	0.2 (4)	C6—N1—C2—C3	−0.1 (4)
C2—C3—C4—C7	177.9 (3)	O1A—C1A—C2A—C2A^i	7.3 (5)
C3—C4—C5—C6	−0.6 (4)	O2A—C1A—C2A—C2A^i	−173.6 (3)
C3—C4—C7—C7^ii	−85.5 (4)	C7—C4—C5—C6	−178.2 (3)

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

4,4'-Ethane-1,2-diyldipyridine succinic acid (ETYSUC_246)

Crystal data

C12H12N2·C4H6O4	F(000) = 640
Mr = 302.32	Dx = 1.537 Mg m^−3
Monoclinic, I2/a	Mo Kα radiation, λ = 0.71073 Å
a = 16.48 (4) Å	Cell parameters from 521 reflections
b = 4.5205 (4) Å	θ = 4.3–22.2°
c = 19.083 (12) Å	µ = 0.11 mm^−1
β = 113.24 (16)°	T = 295 K
V = 1307 (4) Å^3	Plate, colourless
Z = 4	0.35 × 0.16 × 0.03 mm

Data collection

Xcalibur, Eos diffractometer	259 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	163 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.076
Detector resolution: 16.1544 pixels mm^-1	θmax = 26.3°, θmin = 2.3°
ω scans	h = −6→6
Absorption correction: gaussian CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022) Numerical absorption correction based on gaussian integration over a multifaceted crystal model (Absorb Angel (2004) J. Appl. Cryst. 37:486-492)	k = −5→5
Tmin = 0.996, Tmax = 0.996	l = −22→23
1924 measured reflections

Refinement

Refinement on F^2	Primary atom site location: iterative
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.058	H-atom parameters constrained
wR(F^2) = 0.187	w = 1/[σ^2(Fo^2) + (0.0939P)^2 + 3.0865P] where P = (Fo^2 + 2Fc^2)/3
S = 1.11	(Δ/σ)max < 0.001
259 reflections	Δρmax = 0.14 e Å^−3
46 parameters	Δρmin = −0.17 e Å^−3
9 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
N1	0.3908 (15)	0.4702 (19)	0.1462 (6)	0.037 (4)*
C2	0.3356 (17)	0.6243 (17)	0.0868 (6)	0.036 (3)*
H2	0.2751	0.5922	0.0694	0.043*
C3	0.3682 (16)	0.833 (2)	0.0507 (7)	0.035 (4)*
H3	0.3289	0.9422	0.0103	0.042*
C4	0.4582 (16)	0.880 (2)	0.0741 (7)	0.027 (4)*
C5	0.5149 (18)	0.7226 (17)	0.1357 (6)	0.029 (3)*
H5	0.5757	0.7486	0.1536	0.035*
C6	0.4776 (15)	0.522 (2)	0.1704 (8)	0.028 (4)*
H6	0.5154	0.4179	0.2128	0.034*
C1A	0.2531 (14)	0.0297 (19)	0.1759 (6)	0.022 (3)*
O1A	0.3353 (14)	0.1014 (14)	0.2122 (5)	0.040 (3)*
H1A	0.3437	0.2676	0.1991	0.060*
C2A	0.2174 (18)	−0.2041 (16)	0.2109 (6)	0.028 (2)*
H2AA	0.2017	−0.3759	0.1777	0.033*
H2AB	0.1641	−0.1315	0.2149	0.033*
O2A	0.2083 (14)	0.1553 (11)	0.1161 (5)	0.038 (2)*
C7	0.4925 (17)	1.0856 (16)	0.0302 (6)	0.028 (2)*
H7A	0.4501	1.2424	0.0073	0.034*
H7B	0.5474	1.1750	0.0643	0.034*

Geometric parameters (Å, º)

N1—C2	1.336 (16)	C1A—O1A	1.30 (2)
N1—C6	1.34 (2)	C1A—C2A	1.489 (18)
C2—H2	0.9300	C1A—O2A	1.228 (12)
C2—C3	1.394 (15)	O1A—H1A	0.8200
C3—H3	0.9300	C2A—C2A^i	1.51 (3)
C3—C4	1.39 (2)	C2A—H2AA	0.9700
C4—C5	1.38 (2)	C2A—H2AB	0.9700
C4—C7	1.503 (14)	C7—C7^ii	1.488 (18)
C5—H5	0.9300	C7—H7A	0.9700
C5—C6	1.400 (15)	C7—H7B	0.9700
C6—H6	0.9300
C2—N1—C6	118.6 (14)	O1A—C1A—C2A	117.0 (12)
N1—C2—H2	119.8	O2A—C1A—O1A	120.0 (13)
N1—C2—C3	120.4 (19)	O2A—C1A—C2A	123.1 (18)
C3—C2—H2	119.8	C1A—O1A—H1A	109.5
C2—C3—H3	119.4	C1A—C2A—C2A^i	113 (2)
C4—C3—C2	121.1 (15)	C1A—C2A—H2AA	109.1
C4—C3—H3	119.4	C1A—C2A—H2AB	109.1
C3—C4—C7	120.4 (15)	C2A^i—C2A—H2AA	109.1
C5—C4—C3	118.3 (14)	C2A^i—C2A—H2AB	109.1
C5—C4—C7	121 (2)	H2AA—C2A—H2AB	107.8
C4—C5—H5	121.2	C4—C7—H7A	109.9
C4—C5—C6	118 (2)	C4—C7—H7B	109.9
C6—C5—H5	121.2	C7^ii—C7—C4	108.9 (10)
N1—C6—C5	124.0 (16)	C7^ii—C7—H7A	109.9
N1—C6—H6	118.0	C7^ii—C7—H7B	109.9
C5—C6—H6	118.0	H7A—C7—H7B	108.3
N1—C2—C3—C4	1.7 (16)	C4—C5—C6—N1	1.4 (15)
C2—N1—C6—C5	−1.9 (18)	C5—C4—C7—C7^ii	87 (2)
C2—C3—C4—C5	−2.2 (18)	C6—N1—C2—C3	0.3 (15)
C2—C3—C4—C7	174.5 (7)	O1A—C1A—C2A—C2A^i	6.4 (19)
C3—C4—C5—C6	0.6 (14)	O2A—C1A—C2A—C2A^i	−172.8 (13)
C3—C4—C7—C7^ii	−89 (2)	C7—C4—C5—C6	−176.0 (8)

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

4,4'-Ethane-1,2-diyldipyridine succinic acid (etysuc_250K)

Crystal data

C12H12N2·C4H6O4	F(000) = 640
Mr = 302.32	Dx = 1.341 Mg m^−3
Monoclinic, I2/a	Cu Kα radiation, λ = 1.54184 Å
a = 16.6494 (14) Å	Cell parameters from 976 reflections
b = 4.9069 (4) Å	θ = 4.8–71.8°
c = 19.3575 (13) Å	µ = 0.81 mm^−1
β = 108.812 (9)°	T = 250 K
V = 1497.0 (2) Å^3	Plate, colourless
Z = 4	0.14 × 0.09 × 0.04 mm

Data collection

SuperNova, Single source at offset/far, Atlas diffractometer	1432 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source	961 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.036
Detector resolution: 10.5384 pixels mm^-1	θmax = 72.3°, θmin = 4.8°
ω scans	h = −20→19
Absorption correction: gaussian CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −5→5
Tmin = 0.904, Tmax = 1.000	l = −17→23
2831 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.053	All H-atom parameters refined
wR(F^2) = 0.165	w = 1/[σ^2(Fo^2) + (0.0878P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
1432 reflections	Δρmax = 0.17 e Å^−3
136 parameters	Δρmin = −0.18 e Å^−3

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
N1	0.39345 (13)	0.4590 (5)	0.14466 (10)	0.0468 (6)
C2	0.34218 (17)	0.5824 (6)	0.08521 (13)	0.0517 (7)
C3	0.37049 (17)	0.7810 (6)	0.04821 (13)	0.0509 (7)
C4	0.45496 (15)	0.8564 (5)	0.07198 (12)	0.0434 (6)
C5	0.50795 (16)	0.7272 (6)	0.13321 (13)	0.0487 (6)
C6	0.47496 (16)	0.5312 (6)	0.16822 (13)	0.0485 (6)
C1A	0.25454 (15)	0.0195 (5)	0.17687 (12)	0.0453 (6)
O1A	0.33347 (11)	0.0883 (4)	0.21111 (9)	0.0553 (5)
C2A	0.22099 (17)	−0.2062 (6)	0.21302 (14)	0.0480 (6)
O2A	0.21144 (12)	0.1247 (4)	0.12033 (9)	0.0596 (6)
C7	0.48817 (19)	1.0654 (6)	0.03107 (14)	0.0493 (7)
H2	0.2823 (18)	0.525 (6)	0.0684 (14)	0.053 (7)*
H1A	0.351 (2)	0.230 (8)	0.181 (2)	0.101 (13)*
H2AA	0.2075 (19)	−0.360 (7)	0.1791 (16)	0.061 (8)*
H2AB	0.171 (2)	−0.135 (7)	0.2174 (16)	0.068 (9)*
H7A	0.541 (2)	1.148 (7)	0.0642 (16)	0.064 (8)*
H6	0.511 (2)	0.443 (7)	0.2117 (16)	0.068 (9)*
H3	0.3290 (19)	0.864 (6)	0.0038 (16)	0.066 (8)*
H7B	0.441 (2)	1.203 (7)	0.0066 (17)	0.071 (9)*
H5	0.5648 (17)	0.767 (6)	0.1513 (13)	0.048 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0494 (11)	0.0542 (13)	0.0431 (10)	−0.0057 (10)	0.0238 (9)	0.0034 (9)
C2	0.0460 (14)	0.0669 (19)	0.0466 (12)	−0.0044 (13)	0.0212 (11)	0.0070 (12)
C3	0.0525 (14)	0.0600 (18)	0.0449 (12)	−0.0011 (13)	0.0221 (11)	0.0103 (12)
C4	0.0526 (14)	0.0460 (14)	0.0398 (11)	−0.0021 (11)	0.0263 (10)	0.0006 (10)
C5	0.0453 (14)	0.0585 (17)	0.0461 (12)	−0.0067 (12)	0.0199 (11)	0.0001 (12)
C6	0.0520 (14)	0.0531 (16)	0.0437 (12)	−0.0025 (12)	0.0199 (11)	0.0059 (11)
C1A	0.0497 (13)	0.0507 (15)	0.0407 (11)	0.0003 (12)	0.0218 (11)	0.0010 (11)
O1A	0.0496 (10)	0.0673 (14)	0.0479 (9)	−0.0127 (9)	0.0141 (8)	0.0134 (9)
C2A	0.0459 (13)	0.0525 (16)	0.0486 (13)	−0.0041 (12)	0.0195 (11)	0.0068 (12)
O2A	0.0544 (11)	0.0703 (14)	0.0528 (10)	−0.0033 (10)	0.0154 (8)	0.0173 (10)
C7	0.0599 (16)	0.0493 (16)	0.0481 (12)	−0.0070 (13)	0.0305 (12)	0.0011 (12)

Geometric parameters (Å, º)

N1—C2	1.337 (3)	C1A—O1A	1.311 (3)
N1—C6	1.333 (3)	C1A—C2A	1.510 (4)
C2—C3	1.379 (4)	C1A—O2A	1.213 (3)
C2—H2	0.99 (3)	O1A—H1A	1.01 (4)
C3—C4	1.382 (4)	C2A—C2A^i	1.509 (5)
C3—H3	1.00 (3)	C2A—H2AA	0.98 (3)
C4—C5	1.382 (4)	C2A—H2AB	0.93 (3)
C4—C7	1.506 (3)	C7—C7^ii	1.523 (5)
C5—C6	1.388 (4)	C7—H7A	0.99 (3)
C5—H5	0.92 (3)	C7—H7B	1.03 (3)
C6—H6	0.96 (3)
C6—N1—C2	118.1 (2)	O1A—C1A—C2A	114.5 (2)
N1—C2—C3	122.5 (3)	O2A—C1A—O1A	123.5 (2)
N1—C2—H2	116.9 (16)	O2A—C1A—C2A	122.0 (2)
C3—C2—H2	120.7 (16)	C1A—O1A—H1A	109 (2)
C2—C3—C4	119.9 (2)	C1A—C2A—H2AA	107.1 (17)
C2—C3—H3	118.6 (18)	C1A—C2A—H2AB	104 (2)
C4—C3—H3	121.6 (18)	C2A^i—C2A—C1A	115.4 (3)
C3—C4—C5	117.5 (2)	C2A^i—C2A—H2AA	110.9 (18)
C3—C4—C7	120.9 (2)	C2A^i—C2A—H2AB	109.8 (19)
C5—C4—C7	121.5 (2)	H2AA—C2A—H2AB	109 (3)
C4—C5—C6	119.5 (2)	C4—C7—C7^ii	111.1 (3)
C4—C5—H5	121.5 (16)	C4—C7—H7A	109.6 (18)
C6—C5—H5	119.0 (16)	C4—C7—H7B	109.3 (17)
N1—C6—C5	122.5 (2)	C7^ii—C7—H7A	106.4 (18)
N1—C6—H6	117.1 (18)	C7^ii—C7—H7B	105.6 (17)
C5—C6—H6	120.4 (18)	H7A—C7—H7B	115 (3)
N1—C2—C3—C4	0.8 (4)	C4—C5—C6—N1	0.7 (4)
C2—N1—C6—C5	−0.3 (4)	C5—C4—C7—C7^ii	92.8 (4)
C2—C3—C4—C5	−0.3 (4)	C6—N1—C2—C3	−0.4 (4)
C2—C3—C4—C7	177.8 (2)	O1A—C1A—C2A—C2A^i	7.1 (4)
C3—C4—C5—C6	−0.4 (4)	O2A—C1A—C2A—C2A^i	−173.6 (3)
C3—C4—C7—C7^ii	−85.2 (4)	C7—C4—C5—C6	−178.5 (2)

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

4,4'-Ethane-1,2-diyldipyridine succinic acid (ETYSUC_276)

Crystal data

C12H12N2·C4H6O4	F(000) = 640
Mr = 302.32	Dx = 1.558 Mg m^−3
Monoclinic, I2/a	Mo Kα radiation, λ = 0.71073 Å
a = 16.469 (14) Å	Cell parameters from 1908 reflections
b = 4.4857 (2) Å	θ = 4.7–26.6°
c = 19.042 (4) Å	µ = 0.11 mm^−1
β = 113.63 (5)°	T = 295 K
V = 1288.7 (12) Å^3	Plate, colourless
Z = 4	0.31 × 0.15 × 0.03 mm

Data collection

Xcalibur, Eos diffractometer	361 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	229 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.081
Detector resolution: 16.1544 pixels mm^-1	θmax = 26.8°, θmin = 4.7°
ω scans	h = −6→6
Absorption correction: gaussian CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022) Numerical absorption correction based on gaussian integration over a multifaceted crystal model (Absorb Angel (2004) J. Appl. Cryst. 37:486-492)	k = −5→5
Tmin = 0.995, Tmax = 0.996	l = −23→23
4834 measured reflections

Refinement

Refinement on F^2	5 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.088	H-atom parameters constrained
wR(F^2) = 0.281	w = 1/[σ^2(Fo^2) + (0.1571P)^2 + 5.0593P] where P = (Fo^2 + 2Fc^2)/3
S = 1.13	(Δ/σ)max < 0.001
361 reflections	Δρmax = 0.22 e Å^−3
46 parameters	Δρmin = −0.30 e Å^−3

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
N1	0.3930 (13)	0.4763 (14)	0.1477 (5)	0.035 (2)*
C2	0.3371 (15)	0.6263 (16)	0.0870 (5)	0.043 (2)*
H2	0.2764	0.5931	0.0695	0.051*
C3	0.370 (2)	0.834 (2)	0.0496 (6)	0.039 (3)*
H3	0.3298	0.9340	0.0069	0.047*
C4	0.4538 (19)	0.8894 (18)	0.0732 (5)	0.032 (3)*
C5	0.5124 (15)	0.7271 (16)	0.1358 (5)	0.036 (2)*
H5	0.5732	0.7573	0.1532	0.043*
C6	0.4799 (15)	0.5268 (19)	0.1705 (6)	0.042 (3)*
H6	0.5194	0.4193	0.2118	0.050*
C1A	0.2536 (12)	0.0328 (15)	0.1754 (5)	0.029 (2)*
O1A	0.3341 (11)	0.1019 (12)	0.2122 (4)	0.050 (2)*
H1A	0.3463	0.2468	0.1920	0.074*
C2A	0.2141 (16)	−0.1989 (15)	0.2110 (5)	0.035 (2)*
H2AA	0.1930	−0.3687	0.1770	0.042*
H2AB	0.1641	−0.1138	0.2188	0.042*
O2A	0.2066 (11)	0.1581 (11)	0.1150 (3)	0.0424 (19)*
C7	0.4897 (15)	1.0882 (15)	0.0304 (5)	0.033 (2)*
H7A	0.5434	1.1827	0.0659	0.039*
H7B	0.4469	1.2436	0.0053	0.039*

Geometric parameters (Å, º)

N1—C2	1.335 (14)	C1A—O1A	1.265 (17)
N1—C6	1.338 (19)	C1A—C2A	1.523 (19)
C2—H2	0.9300	C1A—O2A	1.234 (10)
C2—C3	1.40 (2)	O1A—H1A	0.8200
C3—H3	0.9300	C2A—C2A^i	1.55 (3)
C3—C4	1.30 (5)	C2A—H2AA	0.9700
C4—C5	1.40 (2)	C2A—H2AB	0.9700
C4—C7	1.48 (2)	C7—C7^ii	1.55 (2)
C5—H5	0.9300	C7—H7A	0.9700
C5—C6	1.347 (19)	C7—H7B	0.9700
C6—H6	0.9300
C2—N1—C6	118.2 (13)	O1A—C1A—C2A	117.4 (10)
N1—C2—H2	119.9	O2A—C1A—O1A	122.1 (11)
N1—C2—C3	120.2 (19)	O2A—C1A—C2A	120.4 (15)
C3—C2—H2	119.9	C1A—O1A—H1A	109.5
C2—C3—H3	119.2	C1A—C2A—C2A^i	109 (2)
C4—C3—C2	121.6 (15)	C1A—C2A—H2AA	109.8
C4—C3—H3	119.2	C1A—C2A—H2AB	109.8
C3—C4—C5	118.1 (14)	C2A^i—C2A—H2AA	109.8
C3—C4—C7	122.1 (13)	C2A^i—C2A—H2AB	109.8
C5—C4—C7	119 (2)	H2AA—C2A—H2AB	108.3
C4—C5—H5	120.3	C4—C7—C7^ii	111.0 (9)
C6—C5—C4	119 (2)	C4—C7—H7A	109.4
C6—C5—H5	120.3	C4—C7—H7B	109.4
N1—C6—C5	122.5 (13)	C7^ii—C7—H7A	109.4
N1—C6—H6	118.7	C7^ii—C7—H7B	109.4
C5—C6—H6	118.7	H7A—C7—H7B	108.0
N1—C2—C3—C4	−1 (2)	C4—C5—C6—N1	−0.3 (15)
C2—N1—C6—C5	1.7 (15)	C5—C4—C7—C7^ii	83.7 (19)
C2—C3—C4—C5	2 (2)	C6—N1—C2—C3	−1.0 (14)
C2—C3—C4—C7	174.6 (8)	O1A—C1A—C2A—C2A^i	0.2 (17)
C3—C4—C5—C6	−1.8 (19)	O2A—C1A—C2A—C2A^i	−175.8 (12)
C3—C4—C7—C7^ii	−88 (3)	C7—C4—C5—C6	−174.2 (8)

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

4,4'-Ethane-1,2-diyldipyridine succinic acid (ETYSUC_287)

Crystal data

C12H12N2·C4H6O4	F(000) = 640
Mr = 302.32	Dx = 1.560 Mg m^−3
Monoclinic, I2/a	Mo Kα radiation, λ = 0.71073 Å
a = 16.462 (12) Å	Cell parameters from 1891 reflections
b = 4.4828 (2) Å	θ = 4.3–24.7°
c = 19.038 (3) Å	µ = 0.11 mm^−1
β = 113.66 (5)°	T = 295 K
V = 1286.9 (10) Å^3	Plate, colourless
Z = 4	0.31 × 0.15 × 0.03 mm

Data collection

Xcalibur, Eos diffractometer	366 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	215 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.086
Detector resolution: 16.1544 pixels mm^-1	θmax = 26.6°, θmin = 2.3°
ω scans	h = −6→6
Absorption correction: gaussian CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022) Numerical absorption correction based on gaussian integration over a multifaceted crystal model (Absorb Angel (2004) J. Appl. Cryst. 37:486-492)	k = −5→5
Tmin = 0.995, Tmax = 0.996	l = −22→22
3855 measured reflections

Refinement

Refinement on F^2	5 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.086	H-atom parameters constrained
wR(F^2) = 0.270	w = 1/[σ^2(Fo^2) + (0.1902P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
366 reflections	Δρmax = 0.19 e Å^−3
46 parameters	Δρmin = −0.25 e Å^−3

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
N1	0.3937 (9)	0.4757 (11)	0.1473 (4)	0.041 (2)*
C2	0.3349 (11)	0.6280 (11)	0.0866 (4)	0.046 (2)*
H2	0.2740	0.6002	0.0699	0.056*
C3	0.3721 (16)	0.8371 (14)	0.0490 (4)	0.039 (2)*
H3	0.3339	0.9368	0.0054	0.046*
C4	0.4549 (14)	0.8887 (13)	0.0734 (4)	0.033 (2)*
C5	0.5141 (10)	0.7263 (13)	0.1363 (4)	0.043 (2)*
H5	0.5749	0.7581	0.1539	0.052*
C6	0.4822 (12)	0.5255 (15)	0.1707 (4)	0.044 (2)*
H6	0.5217	0.4169	0.2118	0.053*
C1A	0.2532 (9)	0.0357 (12)	0.1742 (4)	0.0325 (18)*
O1A	0.3335 (8)	0.1023 (9)	0.2116 (3)	0.0503 (17)*
H1A	0.3419	0.2761	0.2028	0.075*
C2A	0.2139 (11)	−0.1979 (12)	0.2110 (4)	0.0392 (19)*
H2AA	0.1922	−0.3676	0.1769	0.047*
H2AB	0.1643	−0.1119	0.2192	0.047*
O2A	0.2059 (9)	0.1615 (8)	0.1149 (2)	0.0470 (16)*
C7	0.4898 (11)	1.0905 (12)	0.0300 (4)	0.0399 (19)*
H7A	0.5435	1.1873	0.0651	0.048*
H7B	0.4464	1.2439	0.0045	0.048*

Geometric parameters (Å, º)

N1—C2	1.357 (12)	C1A—O1A	1.261 (14)
N1—C6	1.359 (17)	C1A—C2A	1.539 (15)
C2—H2	0.9300	C1A—O2A	1.222 (9)
C2—C3	1.456 (19)	O1A—H1A	0.8200
C3—H3	0.9300	C2A—C2A^i	1.56 (2)
C3—C4	1.27 (3)	C2A—H2AA	0.9700
C4—C5	1.406 (15)	C2A—H2AB	0.9700
C4—C7	1.488 (16)	C7—C7^ii	1.544 (17)
C5—H5	0.9300	C7—H7A	0.9700
C5—C6	1.338 (15)	C7—H7B	0.9700
C6—H6	0.9300
C2—N1—C6	120.1 (9)	O1A—C1A—C2A	116.2 (7)
N1—C2—H2	121.8	O2A—C1A—O1A	123.1 (9)
N1—C2—C3	116.4 (15)	O2A—C1A—C2A	120.4 (12)
C3—C2—H2	121.8	C1A—O1A—H1A	109.5
C2—C3—H3	118.7	C1A—C2A—C2A^i	109.8 (15)
C4—C3—C2	122.5 (11)	C1A—C2A—H2AA	109.7
C4—C3—H3	118.7	C1A—C2A—H2AB	109.7
C3—C4—C5	119.5 (11)	C2A^i—C2A—H2AA	109.7
C3—C4—C7	120.2 (9)	C2A^i—C2A—H2AB	109.7
C5—C4—C7	119.8 (16)	H2AA—C2A—H2AB	108.2
C4—C5—H5	120.3	C4—C7—C7^ii	109.8 (7)
C6—C5—C4	119.4 (15)	C4—C7—H7A	109.7
C6—C5—H5	120.3	C4—C7—H7B	109.7
N1—C6—H6	119.0	C7^ii—C7—H7A	109.7
C5—C6—N1	122.0 (10)	C7^ii—C7—H7B	109.7
C5—C6—H6	119.0	H7A—C7—H7B	108.2
N1—C2—C3—C4	−3.7 (15)	C4—C5—C6—N1	−0.8 (12)
C2—N1—C6—C5	1.1 (12)	C5—C4—C7—C7^ii	83.5 (14)
C2—C3—C4—C5	4.0 (18)	C6—N1—C2—C3	1.0 (10)
C2—C3—C4—C7	176.2 (6)	O1A—C1A—C2A—C2A^i	−0.3 (12)
C3—C4—C5—C6	−1.8 (15)	O2A—C1A—C2A—C2A^i	−175.2 (9)
C3—C4—C7—C7^ii	−88.7 (18)	C7—C4—C5—C6	−174.0 (6)

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

4,4'-Ethane-1,2-diyldipyridine succinic acid (ETYSUC_290)

Crystal data

C12H12N2·C4H6O4	F(000) = 640
Mr = 302.32	Dx = 1.569 Mg m^−3
Monoclinic, I2/a	Mo Kα radiation, λ = 0.71073 Å
a = 16.446 (10) Å	Cell parameters from 1681 reflections
b = 4.46879 (18) Å	θ = 4.7–23.7°
c = 19.038 (3) Å	µ = 0.11 mm^−1
β = 113.81 (4)°	T = 295 K
V = 1280.2 (9) Å^3	Plate, colourless
Z = 4	0.31 × 0.15 × 0.03 mm

Data collection

Xcalibur, Eos diffractometer	211 reflections with I > 2σ(I)
Detector resolution: 16.1544 pixels mm^-1	Rint = 0.076
phi and ω scans	θmax = 26.6°, θmin = 2.3°
Absorption correction: gaussian CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022) Numerical absorption correction based on gaussian integration over a multifaceted crystal model (Absorb Angel (2004) J. Appl. Cryst. 37:486-492)	h = −6→6
Tmin = 0.995, Tmax = 0.996	k = −5→5
2572 measured reflections	l = −22→22
314 independent reflections

Refinement

Refinement on F^2	5 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.060	H-atom parameters constrained
wR(F^2) = 0.174	w = 1/[σ^2(Fo^2) + (0.115P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
314 reflections	Δρmax = 0.15 e Å^−3
46 parameters	Δρmin = −0.21 e Å^−3

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
N1	0.3917 (9)	0.4737 (10)	0.1475 (3)	0.0314 (19)*
C2	0.3356 (10)	0.6271 (11)	0.0870 (3)	0.0317 (19)*
H2	0.2748	0.5928	0.0694	0.038*
C3	0.3673 (15)	0.8396 (13)	0.0496 (4)	0.030 (2)*
H3	0.3276	0.9478	0.0083	0.036*
C4	0.4573 (12)	0.8866 (12)	0.0744 (4)	0.0220 (19)*
C5	0.5129 (9)	0.7243 (11)	0.1357 (3)	0.0260 (17)*
H5	0.5740	0.7518	0.1539	0.031*
C6	0.4795 (11)	0.5249 (14)	0.1698 (4)	0.030 (2)*
H6	0.5191	0.4161	0.2111	0.036*
C1A	0.2533 (9)	0.0369 (12)	0.1756 (3)	0.0254 (17)*
O1A	0.3356 (8)	0.1007 (9)	0.2122 (3)	0.0430 (15)*
H1A	0.3500	0.2302	0.1889	0.065*
C2A	0.2145 (11)	−0.2005 (11)	0.2110 (3)	0.0316 (18)*
H2AA	0.1949	−0.3715	0.1769	0.038*
H2AB	0.1635	−0.1192	0.2179	0.038*
O2A	0.2053 (8)	0.1593 (7)	0.1145 (2)	0.0341 (14)*
C7	0.4898 (10)	1.0890 (12)	0.0305 (3)	0.0273 (16)*
H7A	0.5432	1.1894	0.0651	0.033*
H7B	0.4452	1.2403	0.0052	0.033*

Geometric parameters (Å, º)

N1—C2	1.339 (11)	C1A—O1A	1.280 (14)
N1—C6	1.350 (16)	C1A—C2A	1.528 (13)
C2—H2	0.9300	C1A—O2A	1.238 (8)
C2—C3	1.407 (14)	O1A—H1A	0.8200
C3—H3	0.9300	C2A—C2A^i	1.54 (2)
C3—C4	1.38 (3)	C2A—H2AA	0.9700
C4—C5	1.365 (13)	C2A—H2AB	0.9700
C4—C7	1.472 (14)	C7—C7^ii	1.552 (16)
C5—H5	0.9300	C7—H7A	0.9700
C5—C6	1.343 (13)	C7—H7B	0.9700
C6—H6	0.9300
C2—N1—C6	117.6 (8)	O1A—C1A—C2A	116.9 (7)
N1—C2—H2	119.6	O2A—C1A—O1A	123.2 (8)
N1—C2—C3	120.9 (13)	O2A—C1A—C2A	119.9 (11)
C3—C2—H2	119.6	C1A—O1A—H1A	109.5
C2—C3—H3	120.1	C1A—C2A—C2A^i	109.7 (15)
C4—C3—C2	119.8 (9)	C1A—C2A—H2AA	109.7
C4—C3—H3	120.1	C1A—C2A—H2AB	109.7
C3—C4—C7	119.1 (9)	C2A^i—C2A—H2AA	109.7
C5—C4—C3	118.0 (10)	C2A^i—C2A—H2AB	109.7
C5—C4—C7	122.7 (16)	H2AA—C2A—H2AB	108.2
C4—C5—H5	119.9	C4—C7—C7^ii	110.4 (6)
C6—C5—C4	120.1 (14)	C4—C7—H7A	109.6
C6—C5—H5	119.9	C4—C7—H7B	109.6
N1—C6—H6	118.2	C7^ii—C7—H7A	109.6
C5—C6—N1	123.6 (9)	C7^ii—C7—H7B	109.6
C5—C6—H6	118.2	H7A—C7—H7B	108.1
N1—C2—C3—C4	1.4 (12)	C4—C5—C6—N1	−0.7 (10)
C2—N1—C6—C5	1.4 (11)	C5—C4—C7—C7^ii	83.1 (13)
C2—C3—C4—C5	−0.6 (14)	C6—N1—C2—C3	−1.7 (10)
C2—C3—C4—C7	174.4 (5)	O1A—C1A—C2A—C2A^i	3.6 (12)
C3—C4—C5—C6	0.2 (12)	O2A—C1A—C2A—C2A^i	−175.8 (9)
C3—C4—C7—C7^ii	−91.6 (16)	C7—C4—C5—C6	−174.6 (5)

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

4,4'-Ethane-1,2-diyldipyridine succinic acid (ETYSUC_297)

Crystal data

C12H12N2·C4H6O4	F(000) = 640
Mr = 302.32	Dx = 1.569 Mg m^−3
Monoclinic, I2/a	Mo Kα radiation, λ = 0.71073 Å
a = 16.33 (7) Å	Cell parameters from 570 reflections
b = 4.4824 (9) Å	θ = 2.3–25.8°
c = 19.06 (2) Å	µ = 0.11 mm^−1
β = 113.4 (3)°	T = 295 K
V = 1280 (7) Å^3	Plate, colourless
Z = 4	0.19 × 0.09 × 0.02 mm

Data collection

New Xcalibur, EosS2 diffractometer	252 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	164 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.097
Detector resolution: 8.0169 pixels mm^-1	θmax = 25.9°, θmin = 2.3°
ω scans	h = −6→7
Absorption correction: gaussian CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022) Numerical absorption correction based on gaussian integration over a multifaceted crystal model (Absorb Angel (2004) J. Appl. Cryst. 37:486-492)	k = −5→5
Tmin = 0.997, Tmax = 0.998	l = −23→20
1082 measured reflections

Refinement

Refinement on F^2	4 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.073	H-atom parameters constrained
wR(F^2) = 0.227	w = 1/[σ^2(Fo^2) + (0.1503P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
252 reflections	Δρmax = 0.23 e Å^−3
46 parameters	Δρmin = −0.28 e Å^−3

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
N1	0.3904 (15)	0.4735 (19)	0.1463 (6)	0.027 (4)*
C2	0.3339 (18)	0.6262 (18)	0.0869 (7)	0.037 (3)*
H2	0.2728	0.5937	0.0701	0.045*
C3	0.367 (3)	0.839 (2)	0.0488 (8)	0.018 (3)*
H3	0.3270	0.9443	0.0070	0.022*
C4	0.461 (3)	0.890 (2)	0.0754 (9)	0.023 (4)*
C5	0.513 (2)	0.7255 (17)	0.1344 (7)	0.030 (3)*
H5	0.5750	0.7467	0.1521	0.036*
C6	0.4783 (17)	0.523 (2)	0.1703 (8)	0.021 (4)*
H6	0.5172	0.4174	0.2124	0.025*
C1A	0.2543 (15)	0.0376 (19)	0.1760 (7)	0.017 (3)*
O1A	0.3373 (15)	0.1017 (14)	0.2131 (6)	0.042 (3)*
H1A	0.3519	0.2323	0.1902	0.063*
C2A	0.214 (2)	−0.2038 (17)	0.2101 (7)	0.026 (3)*
H2AA	0.1964	−0.3757	0.1764	0.031*
H2AB	0.1614	−0.1268	0.2158	0.031*
O2A	0.2057 (14)	0.1568 (11)	0.1147 (5)	0.029 (2)*
C7	0.4883 (19)	1.0932 (15)	0.0298 (7)	0.019 (2)*
H7A	0.5401	1.2065	0.0624	0.022*
H7B	0.4404	1.2320	0.0033	0.022*

Geometric parameters (Å, º)

N1—C2	1.331 (17)	C1A—O1A	1.29 (2)
N1—C6	1.34 (2)	C1A—C2A	1.54 (2)
C2—H2	0.9300	C1A—O2A	1.242 (15)
C2—C3	1.42 (2)	O1A—H1A	0.8200
C3—H3	0.9300	C2A—C2A^i	1.56 (4)
C3—C4	1.44 (6)	C2A—H2AA	0.9700
C4—C5	1.33 (3)	C2A—H2AB	0.9700
C4—C7	1.445 (19)	C7—C7^ii	1.57 (2)
C5—H5	0.9300	C7—H7A	0.9700
C5—C6	1.39 (2)	C7—H7B	0.9700
C6—H6	0.9300
C2—N1—C6	119.4 (14)	O1A—C1A—C2A	117.4 (13)
N1—C2—H2	119.8	O2A—C1A—O1A	124.0 (14)
N1—C2—C3	120 (2)	O2A—C1A—C2A	118.6 (19)
C3—C2—H2	119.8	C1A—O1A—H1A	109.5
C2—C3—H3	120.2	C1A—C2A—C2A^i	108 (3)
C2—C3—C4	119.6 (19)	C1A—C2A—H2AA	110.0
C4—C3—H3	120.2	C1A—C2A—H2AB	110.0
C3—C4—C7	115.5 (19)	C2A^i—C2A—H2AA	110.0
C5—C4—C3	116 (2)	C2A^i—C2A—H2AB	110.0
C5—C4—C7	128 (3)	H2AA—C2A—H2AB	108.4
C4—C5—H5	119.1	C4—C7—C7^ii	108.7 (10)
C4—C5—C6	122 (3)	C4—C7—H7A	110.0
C6—C5—H5	119.1	C4—C7—H7B	110.0
N1—C6—C5	122.3 (16)	C7^ii—C7—H7A	110.0
N1—C6—H6	118.9	C7^ii—C7—H7B	110.0
C5—C6—H6	118.9	H7A—C7—H7B	108.3
N1—C2—C3—C4	−0.5 (19)	C4—C5—C6—N1	2.2 (16)
C2—N1—C6—C5	−1.1 (18)	C5—C4—C7—C7^ii	79 (2)
C2—C3—C4—C5	1 (2)	C6—N1—C2—C3	0.3 (16)
C2—C3—C4—C7	175.6 (7)	O1A—C1A—C2A—C2A^i	5.4 (19)
C3—C4—C5—C6	−2.3 (18)	O2A—C1A—C2A—C2A^i	−175.2 (13)
C3—C4—C7—C7^ii	−94 (3)	C7—C4—C5—C6	−175.5 (9)

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

1,2-bis(4,4'-pyridyl)ethane succinic acid (ETYSUC_300K_B)

Crystal data

C12H12N2·C4H6O4	F(000) = 640
Mr = 302.32	Dx = 1.331 Mg m^−3
Monoclinic, I2/a	Cu Kα radiation, λ = 1.54184 Å
a = 16.6688 (5) Å	Cell parameters from 2102 reflections
b = 4.9269 (1) Å	θ = 4.2–71.3°
c = 19.3733 (6) Å	µ = 0.80 mm^−1
β = 108.522 (3)°	T = 300 K
V = 1508.63 (8) Å^3	Plate, colourless
Z = 4	0.47 × 0.41 × 0.12 mm

Data collection

New Xcalibur, EosS2 diffractometer	1432 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Cu) X-ray Source	1276 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
Detector resolution: 8.0294 pixels mm^-1	θmax = 71.4°, θmin = 4.8°
ω scans	h = −20→19
Absorption correction: gaussian CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −5→5
Tmin = 0.767, Tmax = 0.923	l = −23→23
4278 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.048	All H-atom parameters refined
wR(F^2) = 0.142	w = 1/[σ^2(Fo^2) + (0.0941P)^2 + 0.2773P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
1432 reflections	Δρmax = 0.18 e Å^−3
136 parameters	Δρmin = −0.32 e Å^−3

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
N1	0.39371 (7)	0.4567 (3)	0.14447 (6)	0.0392 (4)
C2	0.34303 (9)	0.5779 (3)	0.08497 (8)	0.0445 (4)
C3	0.37067 (9)	0.7760 (3)	0.04769 (8)	0.0439 (4)
C4	0.45497 (9)	0.8548 (3)	0.07190 (7)	0.0359 (4)
C5	0.50763 (9)	0.7268 (3)	0.13309 (8)	0.0406 (4)
C6	0.47474 (9)	0.5319 (3)	0.16770 (8)	0.0410 (4)
C1A	0.25508 (8)	0.0185 (3)	0.17694 (7)	0.0358 (4)
O1A	0.33364 (6)	0.0854 (2)	0.21075 (6)	0.0502 (4)
C2A	0.22127 (9)	−0.2053 (3)	0.21334 (8)	0.0416 (4)
O2A	0.21238 (7)	0.1226 (3)	0.12090 (6)	0.0552 (4)
C7	0.48799 (11)	1.0641 (3)	0.03117 (8)	0.0421 (4)
H2AA	0.2064 (14)	−0.349 (5)	0.1773 (13)	0.081 (7)*
H6	0.5105 (12)	0.444 (4)	0.2103 (11)	0.055 (5)*
H2	0.2836 (11)	0.516 (4)	0.0690 (10)	0.047 (4)*
H3	0.3293 (11)	0.862 (4)	0.0057 (10)	0.051 (5)*
H5	0.5675 (11)	0.771 (4)	0.1524 (9)	0.050 (5)*
H2AB	0.1681 (13)	−0.140 (4)	0.2154 (10)	0.064 (6)*
H7A	0.5394 (13)	1.152 (4)	0.0645 (12)	0.061 (5)*
H7B	0.4450 (13)	1.199 (4)	0.0110 (10)	0.061 (5)*
H1A	0.3514 (14)	0.220 (5)	0.1823 (12)	0.082 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0402 (7)	0.0403 (7)	0.0395 (7)	−0.0069 (5)	0.0158 (5)	0.0052 (5)
C2	0.0326 (7)	0.0538 (9)	0.0471 (8)	−0.0066 (6)	0.0124 (6)	0.0093 (7)
C3	0.0379 (7)	0.0502 (9)	0.0427 (8)	0.0000 (6)	0.0116 (6)	0.0127 (6)
C4	0.0429 (7)	0.0331 (7)	0.0375 (7)	−0.0048 (5)	0.0209 (6)	−0.0016 (5)
C5	0.0362 (7)	0.0437 (8)	0.0414 (8)	−0.0083 (6)	0.0117 (6)	0.0003 (6)
C6	0.0400 (8)	0.0438 (8)	0.0365 (7)	−0.0051 (6)	0.0085 (6)	0.0068 (6)
C1A	0.0355 (7)	0.0350 (7)	0.0368 (7)	−0.0029 (5)	0.0116 (6)	0.0024 (5)
O1A	0.0402 (6)	0.0577 (7)	0.0470 (7)	−0.0166 (5)	0.0057 (5)	0.0178 (5)
C2A	0.0358 (7)	0.0417 (8)	0.0456 (9)	−0.0075 (6)	0.0104 (6)	0.0080 (6)
O2A	0.0455 (6)	0.0614 (8)	0.0520 (7)	−0.0058 (5)	0.0062 (5)	0.0223 (5)
C7	0.0530 (9)	0.0340 (8)	0.0461 (8)	−0.0062 (6)	0.0254 (7)	0.0016 (6)

Geometric parameters (Å, º)

N1—C2	1.3341 (19)	C1A—O1A	1.3067 (17)
N1—C6	1.3334 (18)	C1A—C2A	1.5110 (19)
C2—C3	1.378 (2)	C1A—O2A	1.2071 (17)
C2—H2	0.986 (17)	O1A—H1A	0.97 (3)
C3—C4	1.388 (2)	C2A—C2A^i	1.505 (3)
C3—H3	0.979 (19)	C2A—H2AA	0.97 (3)
C4—C5	1.383 (2)	C2A—H2AB	0.95 (2)
C4—C7	1.5049 (18)	C7—C7^ii	1.525 (3)
C5—C6	1.381 (2)	C7—H7A	0.99 (2)
C5—H5	0.973 (17)	C7—H7B	0.96 (2)
C6—H6	0.953 (19)
C6—N1—C2	117.58 (12)	O1A—C1A—C2A	114.39 (12)
N1—C2—C3	122.99 (13)	O2A—C1A—O1A	123.67 (13)
N1—C2—H2	115.5 (11)	O2A—C1A—C2A	121.93 (12)
C3—C2—H2	121.5 (11)	C1A—O1A—H1A	109.1 (13)
C2—C3—C4	119.50 (13)	C1A—C2A—H2AA	104.2 (14)
C2—C3—H3	118.5 (10)	C1A—C2A—H2AB	105.3 (13)
C4—C3—H3	122.0 (10)	C2A^i—C2A—C1A	115.74 (15)
C3—C4—C7	120.94 (13)	C2A^i—C2A—H2AA	113.9 (14)
C5—C4—C3	117.44 (12)	C2A^i—C2A—H2AB	112.3 (12)
C5—C4—C7	121.58 (13)	H2AA—C2A—H2AB	104.3 (17)
C4—C5—H5	121.4 (11)	C4—C7—C7^ii	111.32 (15)
C6—C5—C4	119.45 (13)	C4—C7—H7A	110.0 (12)
C6—C5—H5	119.1 (11)	C4—C7—H7B	109.6 (12)
N1—C6—C5	123.03 (13)	C7^ii—C7—H7A	107.8 (12)
N1—C6—H6	117.0 (11)	C7^ii—C7—H7B	108.2 (12)
C5—C6—H6	119.9 (11)	H7A—C7—H7B	109.9 (16)
N1—C2—C3—C4	0.5 (3)	C4—C5—C6—N1	0.8 (2)
C2—N1—C6—C5	0.0 (2)	C5—C4—C7—C7^ii	93.3 (2)
C2—C3—C4—C5	0.3 (2)	C6—N1—C2—C3	−0.6 (2)
C2—C3—C4—C7	178.01 (14)	O1A—C1A—C2A—C2A^i	6.8 (2)
C3—C4—C5—C6	−0.9 (2)	O2A—C1A—C2A—C2A^i	−173.94 (18)
C3—C4—C7—C7^ii	−84.4 (2)	C7—C4—C5—C6	−178.58 (13)

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

4,4'-Ethane-1,2-diyldipyridine succinic acid (etysuc_300K)

Crystal data

C12H12N2·C4H6O4	F(000) = 640
Mr = 302.32	Dx = 1.331 Mg m^−3
Monoclinic, I2/a	Cu Kα radiation, λ = 1.54184 Å
a = 16.6610 (13) Å	Cell parameters from 927 reflections
b = 4.9284 (4) Å	θ = 4.8–71.2°
c = 19.3767 (13) Å	µ = 0.80 mm^−1
β = 108.520 (8)°	T = 300 K
V = 1508.7 (2) Å^3	Plate, colourless
Z = 4	0.14 × 0.09 × 0.04 mm

Data collection

SuperNova, Single source at offset/far, Atlas diffractometer	1444 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source	914 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.034
Detector resolution: 10.5384 pixels mm^-1	θmax = 72.4°, θmin = 4.8°
ω scans	h = −20→19
Absorption correction: gaussian CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −5→5
Tmin = 0.907, Tmax = 1.000	l = −17→23
2850 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.052	All H-atom parameters refined
wR(F^2) = 0.154	w = 1/[σ^2(Fo^2) + (0.0756P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max < 0.001
1444 reflections	Δρmax = 0.15 e Å^−3
136 parameters	Δρmin = −0.19 e Å^−3

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
N1	0.39363 (13)	0.4555 (4)	0.14440 (10)	0.0534 (6)
C2	0.34321 (17)	0.5778 (6)	0.08502 (14)	0.0585 (7)
C3	0.37098 (17)	0.7766 (6)	0.04758 (14)	0.0585 (7)
C4	0.45509 (15)	0.8547 (5)	0.07181 (12)	0.0484 (6)
C5	0.50740 (16)	0.7267 (6)	0.13288 (13)	0.0556 (7)
C6	0.47485 (16)	0.5319 (6)	0.16778 (13)	0.0554 (7)
C1A	0.25494 (15)	0.0190 (5)	0.17705 (12)	0.0518 (6)
O1A	0.33364 (11)	0.0860 (4)	0.21075 (9)	0.0644 (6)
C2A	0.22126 (17)	−0.2046 (6)	0.21356 (14)	0.0551 (6)
O2A	0.21224 (12)	0.1221 (4)	0.12072 (10)	0.0698 (6)
C7	0.4876 (2)	1.0643 (6)	0.03101 (15)	0.0572 (7)
H2AA	0.1660 (18)	−0.137 (6)	0.2160 (15)	0.071 (8)*
H6	0.5124 (18)	0.432 (6)	0.2115 (15)	0.070 (8)*
H2	0.2858 (16)	0.512 (5)	0.0684 (12)	0.051 (7)*
H1A	0.357 (2)	0.231 (7)	0.1813 (18)	0.106 (12)*
H3	0.3295 (19)	0.862 (6)	0.0031 (16)	0.077 (9)*
H7A	0.441 (2)	1.200 (7)	0.0057 (18)	0.090 (11)*
H7B	0.537 (2)	1.154 (7)	0.0634 (17)	0.084 (10)*
H2AB	0.212 (2)	−0.365 (7)	0.1817 (18)	0.092 (11)*
H5	0.5674 (17)	0.759 (5)	0.1504 (13)	0.062 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0559 (12)	0.0606 (13)	0.0497 (11)	−0.0061 (10)	0.0253 (9)	0.0059 (10)
C2	0.0491 (14)	0.0748 (19)	0.0553 (14)	−0.0081 (13)	0.0221 (11)	0.0071 (13)
C3	0.0570 (15)	0.0690 (18)	0.0536 (13)	0.0005 (13)	0.0233 (11)	0.0128 (13)
C4	0.0579 (14)	0.0494 (13)	0.0473 (12)	−0.0041 (11)	0.0302 (11)	0.0015 (11)
C5	0.0530 (15)	0.0643 (17)	0.0537 (13)	−0.0099 (13)	0.0230 (11)	−0.0019 (12)
C6	0.0581 (15)	0.0601 (16)	0.0500 (13)	−0.0062 (13)	0.0200 (11)	0.0057 (12)
C1A	0.0553 (14)	0.0593 (16)	0.0465 (12)	−0.0015 (12)	0.0243 (11)	0.0028 (12)
O1A	0.0552 (11)	0.0797 (14)	0.0566 (10)	−0.0167 (9)	0.0155 (8)	0.0164 (10)
C2A	0.0523 (14)	0.0589 (17)	0.0572 (13)	−0.0053 (13)	0.0216 (11)	0.0094 (13)
O2A	0.0620 (11)	0.0829 (14)	0.0621 (11)	−0.0070 (10)	0.0162 (9)	0.0210 (10)
C7	0.0719 (17)	0.0545 (16)	0.0567 (14)	−0.0088 (14)	0.0366 (13)	0.0024 (13)

Geometric parameters (Å, º)

N1—C2	1.334 (3)	C1A—O1A	1.308 (3)
N1—C6	1.337 (3)	C1A—C2A	1.511 (3)
C2—C3	1.383 (4)	C1A—O2A	1.209 (3)
C2—H2	0.96 (3)	O1A—H1A	1.06 (4)
C3—C4	1.384 (4)	C2A—C2A^i	1.501 (5)
C3—H3	1.01 (3)	C2A—H2AA	0.99 (3)
C4—C5	1.379 (4)	C2A—H2AB	0.98 (4)
C4—C7	1.502 (3)	C7—C7^ii	1.527 (5)
C5—C6	1.381 (4)	C7—H7A	1.02 (3)
C5—H5	0.96 (3)	C7—H7B	0.97 (3)
C6—H6	1.01 (3)
C2—N1—C6	117.2 (2)	O1A—C1A—C2A	114.4 (2)
N1—C2—C3	123.3 (3)	O2A—C1A—O1A	123.6 (2)
N1—C2—H2	114.9 (15)	O2A—C1A—C2A	122.0 (2)
C3—C2—H2	121.8 (15)	C1A—O1A—H1A	112.2 (18)
C2—C3—C4	119.4 (2)	C1A—C2A—H2AA	105.4 (17)
C2—C3—H3	119.4 (18)	C1A—C2A—H2AB	107.5 (19)
C4—C3—H3	121.2 (18)	C2A^i—C2A—C1A	115.9 (3)
C3—C4—C7	120.6 (2)	C2A^i—C2A—H2AA	112.2 (16)
C5—C4—C3	117.4 (2)	C2A^i—C2A—H2AB	106 (2)
C5—C4—C7	122.0 (2)	H2AA—C2A—H2AB	110 (3)
C4—C5—C6	119.9 (2)	C4—C7—C7^ii	111.2 (3)
C4—C5—H5	122.0 (16)	C4—C7—H7A	110.9 (19)
C6—C5—H5	117.9 (16)	C4—C7—H7B	110.5 (19)
N1—C6—C5	122.9 (2)	C7^ii—C7—H7A	104.3 (19)
N1—C6—H6	116.1 (16)	C7^ii—C7—H7B	108.1 (19)
C5—C6—H6	121.0 (16)	H7A—C7—H7B	112 (3)
N1—C2—C3—C4	0.3 (4)	C4—C5—C6—N1	1.1 (4)
C2—N1—C6—C5	−0.6 (4)	C5—C4—C7—C7^ii	92.8 (4)
C2—C3—C4—C5	0.3 (4)	C6—N1—C2—C3	−0.1 (4)
C2—C3—C4—C7	178.2 (2)	O1A—C1A—C2A—C2A^i	6.4 (4)
C3—C4—C5—C6	−0.9 (4)	O2A—C1A—C2A—C2A^i	−174.7 (3)
C3—C4—C7—C7^ii	−85.1 (4)	C7—C4—C5—C6	−178.8 (2)

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

4,4'-Ethane-1,2-diyldipyridine succinic acid (ETYSUC_329)

Crystal data

C12H12N2·C4H6O4	F(000) = 640
Mr = 302.32	Dx = 1.595 Mg m^−3
Monoclinic, I2/a	Mo Kα radiation, λ = 0.71073 Å
a = 16.429 (12) Å	Cell parameters from 1430 reflections
b = 4.4214 (3) Å	θ = 4.7–24.4°
c = 19.020 (4) Å	µ = 0.12 mm^−1
β = 114.32 (5)°	T = 295 K
V = 1258.9 (11) Å^3	Plate, colourless
Z = 4	0.31 × 0.15 × 0.03 mm

Data collection

Xcalibur, Eos diffractometer	353 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	241 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.082
Detector resolution: 16.1544 pixels mm^-1	θmax = 26.8°, θmin = 2.4°
ω scans	h = −6→6
Absorption correction: gaussian CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022) Numerical absorption correction based on gaussian integration over a multifaceted crystal model (Absorb Angel (2004) J. Appl. Cryst. 37:486-492)	k = −5→5
Tmin = 0.995, Tmax = 0.997	l = −23→23
4135 measured reflections

Refinement

Refinement on F^2	4 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.062	H-atom parameters constrained
wR(F^2) = 0.162	w = 1/[σ^2(Fo^2) + (0.0646P)^2 + 5.1287P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
353 reflections	Δρmax = 0.18 e Å^−3
46 parameters	Δρmin = −0.23 e Å^−3

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
N1	0.3927 (10)	0.4769 (11)	0.1481 (4)	0.0318 (18)*
C2	0.3342 (11)	0.6335 (12)	0.0879 (4)	0.0347 (18)*
H2	0.2731	0.6012	0.0713	0.042*
C3	0.3657 (15)	0.8452 (14)	0.0504 (4)	0.030 (2)*
H3	0.3250	0.9565	0.0096	0.035*
C4	0.4568 (13)	0.8925 (13)	0.0732 (4)	0.0229 (18)*
C5	0.5153 (12)	0.7247 (12)	0.1358 (3)	0.0289 (17)*
H5	0.5768	0.7483	0.1537	0.035*
C6	0.4790 (11)	0.5230 (14)	0.1704 (4)	0.029 (2)*
H6	0.5182	0.4121	0.2122	0.035*
C1A	0.2529 (10)	0.0385 (12)	0.1755 (4)	0.0229 (16)*
O1A	0.3345 (8)	0.1029 (9)	0.2123 (3)	0.0407 (14)*
H1A	0.3466	0.2529	0.1932	0.061*
C2A	0.2174 (12)	−0.1999 (12)	0.2109 (4)	0.0311 (16)*
H2AA	0.2000	−0.3740	0.1769	0.037*
H2AB	0.1643	−0.1233	0.2151	0.037*
O2A	0.2040 (8)	0.1621 (8)	0.1137 (2)	0.0348 (13)*
C7	0.4911 (11)	1.0957 (12)	0.0302 (3)	0.0253 (15)*
H7A	0.5460	1.1915	0.0653	0.030*
H7B	0.4477	1.2526	0.0046	0.030*

Geometric parameters (Å, º)

N1—C2	1.345 (12)	C1A—O1A	1.262 (15)
N1—C6	1.318 (17)	C1A—C2A	1.492 (14)
C2—H2	0.9300	C1A—O2A	1.245 (9)
C2—C3	1.398 (16)	O1A—H1A	0.8200
C3—H3	0.9300	C2A—C2A^i	1.497 (19)
C3—C4	1.39 (3)	C2A—H2AA	0.9700
C4—C5	1.396 (14)	C2A—H2AB	0.9700
C4—C7	1.474 (16)	C7—C7^ii	1.548 (18)
C5—H5	0.9300	C7—H7A	0.9700
C5—C6	1.380 (16)	C7—H7B	0.9700
C6—H6	0.9300
C6—N1—C2	119.4 (10)	O1A—C1A—C2A	115.6 (8)
N1—C2—H2	120.2	O2A—C1A—O1A	123.3 (9)
N1—C2—C3	119.6 (14)	O2A—C1A—C2A	121.1 (12)
C3—C2—H2	120.2	C1A—O1A—H1A	109.5
C2—C3—H3	119.4	C1A—C2A—C2A^i	113.9 (16)
C4—C3—C2	121.2 (10)	C1A—C2A—H2AA	108.8
C4—C3—H3	119.4	C1A—C2A—H2AB	108.8
C3—C4—C5	117.3 (11)	C2A^i—C2A—H2AA	108.8
C3—C4—C7	121.8 (10)	C2A^i—C2A—H2AB	108.8
C5—C4—C7	120.8 (17)	H2AA—C2A—H2AB	107.7
C4—C5—H5	121.0	C4—C7—C7^ii	108.1 (7)
C6—C5—C4	118.0 (16)	C4—C7—H7A	110.1
C6—C5—H5	121.0	C4—C7—H7B	110.1
N1—C6—C5	124.4 (10)	C7^ii—C7—H7A	110.1
N1—C6—H6	117.8	C7^ii—C7—H7B	110.1
C5—C6—H6	117.8	H7A—C7—H7B	108.4
N1—C2—C3—C4	1.5 (12)	C4—C5—C6—N1	0.2 (11)
C2—N1—C6—C5	0.0 (12)	C5—C4—C7—C7^ii	83.7 (14)
C2—C3—C4—C5	−1.3 (14)	C6—N1—C2—C3	−0.8 (11)
C2—C3—C4—C7	174.7 (5)	O1A—C1A—C2A—C2A^i	6.3 (15)
C3—C4—C5—C6	0.5 (12)	O2A—C1A—C2A—C2A^i	−173.9 (11)
C3—C4—C7—C7^ii	−92.2 (17)	C7—C4—C5—C6	−175.6 (6)

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

4,4'-Ethane-1,2-diyldipyridine succinic acid (ETYSUC_347)

Crystal data

C12H12N2·C4H6O4	F(000) = 640
Mr = 302.32	Dx = 1.598 Mg m^−3
Monoclinic, I2/a	Mo Kα radiation, λ = 0.71073 Å
a = 16.44 (9) Å	Cell parameters from 540 reflections
b = 4.4104 (11) Å	θ = 2.3–23.9°
c = 18.97 (3) Å	µ = 0.12 mm^−1
β = 114.0 (4)°	T = 295 K
V = 1256 (8) Å^3	Plate, colourless
Z = 4	0.19 × 0.09 × 0.02 mm

Data collection

New Xcalibur, EosS2 diffractometer	289 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	181 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.095
Detector resolution: 8.0169 pixels mm^-1	θmax = 26.3°, θmin = 2.4°
ω scans	h = −7→7
Absorption correction: gaussian CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022) Numerical absorption correction based on gaussian integration over a multifaceted crystal model (Absorb Angel (2004) J. Appl. Cryst. 37:486-492)	k = −5→5
Tmin = 0.998, Tmax = 0.998	l = −23→23
1431 measured reflections

Refinement

Refinement on F^2	4 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.066	H-atom parameters constrained
wR(F^2) = 0.187	w = 1/[σ^2(Fo^2) + (0.0916P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.11	(Δ/σ)max < 0.001
289 reflections	Δρmax = 0.16 e Å^−3
46 parameters	Δρmin = −0.32 e Å^−3

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
N1	0.3902 (14)	0.4749 (15)	0.1471 (6)	0.036 (3)*
C2	0.3362 (15)	0.6336 (15)	0.0878 (6)	0.035 (3)*
H2	0.2753	0.5997	0.0703	0.042*
C3	0.365 (2)	0.8463 (19)	0.0503 (7)	0.030 (4)*
H3	0.3242	0.9611	0.0104	0.036*
C4	0.459 (2)	0.8884 (18)	0.0740 (8)	0.023 (3)*
C5	0.5172 (17)	0.7238 (15)	0.1366 (6)	0.031 (3)*
H5	0.5786	0.7458	0.1549	0.038*
C6	0.4772 (15)	0.5198 (17)	0.1710 (7)	0.020 (3)*
H6	0.5148	0.4093	0.2136	0.023*
C1A	0.2514 (13)	0.0398 (18)	0.1737 (7)	0.025 (3)*
O1A	0.3342 (13)	0.0998 (13)	0.2125 (5)	0.038 (2)*
H1A	0.3486	0.2441	0.1928	0.057*
C2A	0.2161 (16)	−0.2007 (13)	0.2103 (6)	0.024 (2)*
H2AA	0.1984	−0.3762	0.1766	0.029*
H2AB	0.1634	−0.1236	0.2154	0.029*
O2A	0.2051 (12)	0.1628 (10)	0.1143 (4)	0.0365 (19)*
C7	0.4921 (16)	1.0933 (15)	0.0296 (6)	0.024 (2)*
H7A	0.5470	1.1897	0.0639	0.029*
H7B	0.4485	1.2502	0.0046	0.029*

Geometric parameters (Å, º)

N1—C2	1.315 (16)	C1A—O1A	1.28 (2)
N1—C6	1.33 (2)	C1A—C2A	1.508 (16)
C2—H2	0.9300	C1A—O2A	1.202 (14)
C2—C3	1.37 (2)	O1A—H1A	0.8200
C3—H3	0.9300	C2A—C2A^i	1.53 (3)
C3—C4	1.44 (5)	C2A—H2AA	0.9700
C4—C5	1.39 (3)	C2A—H2AB	0.9700
C4—C7	1.482 (18)	C7—C7^ii	1.499 (16)
C5—H5	0.9300	C7—H7A	0.9700
C5—C6	1.420 (19)	C7—H7B	0.9700
C6—H6	0.9300
C2—N1—C6	118.1 (13)	O1A—C1A—C2A	113.4 (12)
N1—C2—H2	118.2	O2A—C1A—O1A	124.3 (13)
N1—C2—C3	124 (2)	O2A—C1A—C2A	122.3 (17)
C3—C2—H2	118.2	C1A—O1A—H1A	109.5
C2—C3—H3	120.7	C1A—C2A—C2A^i	113 (2)
C2—C3—C4	118.7 (19)	C1A—C2A—H2AA	109.0
C4—C3—H3	120.7	C1A—C2A—H2AB	109.0
C3—C4—C7	119.9 (18)	C2A^i—C2A—H2AA	109.0
C5—C4—C3	118.6 (15)	C2A^i—C2A—H2AB	109.0
C5—C4—C7	121 (3)	H2AA—C2A—H2AB	107.8
C4—C5—H5	122.0	C4—C7—C7^ii	107.9 (9)
C4—C5—C6	116 (2)	C4—C7—H7A	110.1
C6—C5—H5	122.0	C4—C7—H7B	110.1
N1—C6—C5	125.0 (14)	C7^ii—C7—H7A	110.1
N1—C6—H6	117.5	C7^ii—C7—H7B	110.1
C5—C6—H6	117.5	H7A—C7—H7B	108.4
N1—C2—C3—C4	3.5 (15)	C4—C5—C6—N1	1.0 (13)
C2—N1—C6—C5	−1.2 (15)	C5—C4—C7—C7^ii	85 (2)
C2—C3—C4—C5	−3.5 (17)	C6—N1—C2—C3	−1.2 (14)
C2—C3—C4—C7	173.7 (6)	O1A—C1A—C2A—C2A^i	5.6 (16)
C3—C4—C5—C6	1.4 (13)	O2A—C1A—C2A—C2A^i	−173.7 (11)
C3—C4—C7—C7^ii	−92 (2)	C7—C4—C5—C6	−175.8 (6)

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

4,4'-Ethane-1,2-diyldipyridine succinic acid (ETYSUC_373)

Crystal data

C12H12N2·C4H6O4	F(000) = 640
Mr = 302.32	Dx = 1.612 Mg m^−3
Monoclinic, I2/a	Mo Kα radiation, λ = 0.71073 Å
a = 16.46 (6) Å	Cell parameters from 521 reflections
b = 4.3839 (7) Å	θ = 2.3–24.1°
c = 18.94 (2) Å	µ = 0.12 mm^−1
β = 114.3 (3)°	T = 295 K
V = 1246 (6) Å^3	Plate, colourless
Z = 4	0.19 × 0.09 × 0.02 mm

Data collection

New Xcalibur, EosS2 diffractometer	253 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	159 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.095
Detector resolution: 8.0169 pixels mm^-1	θmax = 26.2°, θmin = 2.4°
ω scans	h = −7→7
Absorption correction: gaussian CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022) Numerical absorption correction based on gaussian integration over a multifaceted crystal model (Absorb Angel (2004) J. Appl. Cryst. 37:486-492)	k = −4→5
Tmin = 0.997, Tmax = 0.998	l = −23→22
1000 measured reflections

Refinement

Refinement on F^2	4 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.090	H-atom parameters constrained
wR(F^2) = 0.271	w = 1/[σ^2(Fo^2) + (0.1895P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
253 reflections	Δρmax = 0.24 e Å^−3
46 parameters	Δρmin = −0.34 e Å^−3

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
N1	0.3896 (17)	0.474 (2)	0.1471 (8)	0.036 (4)*
C2	0.3342 (19)	0.636 (2)	0.0873 (7)	0.033 (3)*
H2	0.2733	0.6007	0.0700	0.039*
C3	0.362 (3)	0.852 (2)	0.0502 (9)	0.030 (5)*
H3	0.3210	0.9726	0.0115	0.036*
C4	0.462 (3)	0.888 (2)	0.0743 (9)	0.017 (4)*
C5	0.518 (2)	0.720 (2)	0.1365 (8)	0.035 (4)*
H5	0.5795	0.7361	0.1551	0.042*
C6	0.4771 (18)	0.522 (2)	0.1704 (9)	0.019 (4)*
H6	0.5148	0.4128	0.2136	0.023*
C1A	0.2523 (17)	0.041 (3)	0.1763 (9)	0.028 (4)*
O1A	0.3362 (17)	0.1000 (19)	0.2124 (7)	0.046 (4)*
H1A	0.3490	0.2457	0.1918	0.069*
C2A	0.221 (2)	−0.2004 (19)	0.2121 (8)	0.028 (3)*
H2AA	0.1660	−0.1317	0.2140	0.033*
H2AB	0.2068	−0.3765	0.1782	0.033*
O2A	0.2064 (16)	0.1624 (15)	0.1152 (6)	0.036 (3)*
C7	0.492 (2)	1.093 (2)	0.0303 (8)	0.027 (3)*
H7A	0.5467	1.1934	0.0642	0.033*
H7B	0.4472	1.2479	0.0054	0.033*

Geometric parameters (Å, º)

N1—C2	1.331 (18)	C1A—O1A	1.29 (2)
N1—C6	1.34 (2)	C1A—C2A	1.46 (2)
C2—H2	0.9300	C1A—O2A	1.215 (16)
C2—C3	1.36 (3)	O1A—H1A	0.8200
C3—H3	0.9300	C2A—C2A^i	1.42 (4)
C3—C4	1.53 (6)	C2A—H2AA	0.9700
C4—C5	1.37 (3)	C2A—H2AB	0.9700
C4—C7	1.44 (2)	C7—C7^ii	1.51 (2)
C5—H5	0.9300	C7—H7A	0.9700
C5—C6	1.40 (3)	C7—H7B	0.9700
C6—H6	0.9300
C2—N1—C6	117.7 (15)	O1A—C1A—C2A	113.8 (15)
N1—C2—H2	118.2	O2A—C1A—O1A	121.7 (17)
N1—C2—C3	124 (3)	O2A—C1A—C2A	124 (2)
C3—C2—H2	118.2	C1A—O1A—H1A	109.5
C2—C3—H3	121.1	C1A—C2A—H2AA	107.7
C2—C3—C4	118 (2)	C1A—C2A—H2AB	107.7
C4—C3—H3	121.1	C2A^i—C2A—C1A	118 (3)
C5—C4—C3	117 (2)	C2A^i—C2A—H2AA	107.7
C5—C4—C7	124 (3)	C2A^i—C2A—H2AB	107.7
C7—C4—C3	118 (2)	H2AA—C2A—H2AB	107.1
C4—C5—H5	121.7	C4—C7—C7^ii	108.1 (11)
C4—C5—C6	117 (3)	C4—C7—H7A	110.1
C6—C5—H5	121.7	C4—C7—H7B	110.1
N1—C6—C5	126.8 (17)	C7^ii—C7—H7A	110.1
N1—C6—H6	116.6	C7^ii—C7—H7B	110.1
C5—C6—H6	116.6	H7A—C7—H7B	108.4
N1—C2—C3—C4	5.4 (18)	C4—C5—C6—N1	2.1 (17)
C2—N1—C6—C5	−3 (2)	C5—C4—C7—C7^ii	84 (3)
C2—C3—C4—C5	−5.6 (19)	C6—N1—C2—C3	−1.5 (19)
C2—C3—C4—C7	173.7 (8)	O1A—C1A—C2A—C2A^i	12 (3)
C3—C4—C5—C6	2.0 (15)	O2A—C1A—C2A—C2A^i	−173.1 (18)
C3—C4—C7—C7^ii	−95 (3)	C7—C4—C5—C6	−177.2 (9)

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

4,4'-Ethane-1,2-diyldipyridine succinic acid (etysuc)

Crystal data

C12H12N2·C4H6O4	F(000) = 640
Mr = 302.32	Dx = 1.331 Mg m^−3
Monoclinic, I2/a	Cu Kα radiation, λ = 1.54184 Å
a = 16.6711 (3) Å	Cell parameters from 6372 reflections
b = 4.9272 (1) Å	θ = 4.2–76.1°
c = 19.3744 (4) Å	µ = 0.80 mm^−1
β = 108.512 (2)°	T = 295 K
V = 1509.10 (5) Å^3	Block, colourless
Z = 4	0.2 × 0.1 × 0.04 mm

Data collection

SuperNova, Single source at offset/far, Atlas diffractometer	1554 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source	1318 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.027
Detector resolution: 10.5384 pixels mm^-1	θmax = 76.2°, θmin = 4.8°
ω scans	h = −21→20
Absorption correction: gaussian CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −5→5
Tmin = 0.813, Tmax = 1.000	l = −24→23
12238 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.037	w = 1/[σ^2(Fo^2) + (0.0553P)^2 + 0.6357P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.105	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.17 e Å^−3
1554 reflections	Δρmin = −0.16 e Å^−3
137 parameters	Extinction correction: SHELXL-2014/7 (Sheldrick 2014, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0011 (2)
Primary atom site location: dual

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
N1	0.39365 (7)	0.4565 (2)	0.14452 (6)	0.0400 (3)
C2	0.34297 (8)	0.5776 (3)	0.08506 (7)	0.0454 (4)
C3	0.37070 (8)	0.7758 (3)	0.04771 (7)	0.0449 (4)
C4	0.45499 (8)	0.8545 (3)	0.07183 (6)	0.0367 (3)
C5	0.50755 (8)	0.7272 (3)	0.13315 (7)	0.0411 (3)
C6	0.47475 (8)	0.5319 (3)	0.16781 (7)	0.0418 (3)
C1A	0.25506 (8)	0.0182 (3)	0.17701 (6)	0.0371 (3)
O1A	0.33368 (6)	0.0856 (2)	0.21085 (5)	0.0512 (3)
C2A	0.22111 (8)	−0.2052 (3)	0.21334 (7)	0.0426 (3)
O2A	0.21229 (6)	0.1228 (2)	0.12076 (5)	0.0560 (3)
C7	0.48802 (10)	1.0641 (3)	0.03119 (8)	0.0431 (3)
H2	0.2839 (10)	0.511 (4)	0.0670 (9)	0.053 (4)*
H2AA	0.1674 (12)	−0.142 (4)	0.2166 (9)	0.066 (5)*
H5	0.5678 (10)	0.770 (4)	0.1524 (9)	0.058 (5)*
H2AB	0.2082 (12)	−0.356 (4)	0.1782 (11)	0.074 (6)*
H7A	0.4435 (11)	1.197 (4)	0.0092 (9)	0.064 (5)*
H6	0.5103 (10)	0.443 (4)	0.2112 (9)	0.055 (5)*
H7B	0.5407 (12)	1.157 (4)	0.0658 (10)	0.064 (5)*
H3	0.3296 (11)	0.862 (4)	0.0042 (9)	0.060 (5)*
H1A	0.3537 (12)	0.227 (5)	0.1830 (11)	0.085 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0415 (6)	0.0421 (7)	0.0389 (5)	−0.0071 (5)	0.0162 (4)	0.0052 (5)
C2	0.0350 (6)	0.0563 (9)	0.0453 (7)	−0.0069 (6)	0.0131 (5)	0.0093 (6)
C3	0.0404 (7)	0.0524 (9)	0.0418 (7)	−0.0016 (6)	0.0130 (5)	0.0121 (6)
C4	0.0442 (6)	0.0348 (7)	0.0373 (6)	−0.0040 (5)	0.0219 (5)	−0.0001 (5)
C5	0.0367 (6)	0.0454 (8)	0.0415 (6)	−0.0090 (5)	0.0129 (5)	0.0008 (6)
C6	0.0416 (7)	0.0458 (8)	0.0363 (6)	−0.0053 (6)	0.0101 (5)	0.0062 (5)
C1A	0.0373 (6)	0.0380 (7)	0.0369 (6)	−0.0028 (5)	0.0128 (5)	0.0026 (5)
O1A	0.0422 (5)	0.0595 (7)	0.0467 (5)	−0.0165 (5)	0.0068 (4)	0.0180 (5)
C2A	0.0374 (6)	0.0435 (8)	0.0454 (7)	−0.0080 (6)	0.0111 (5)	0.0086 (6)
O2A	0.0461 (5)	0.0645 (7)	0.0513 (6)	−0.0060 (5)	0.0065 (4)	0.0219 (5)
C7	0.0558 (8)	0.0362 (8)	0.0454 (7)	−0.0067 (6)	0.0275 (6)	0.0022 (6)

Geometric parameters (Å, º)

N1—C2	1.3339 (17)	C1A—O1A	1.3086 (15)
N1—C6	1.3350 (16)	C1A—C2A	1.5101 (18)
C2—C3	1.3793 (19)	C1A—O2A	1.2118 (15)
C2—H2	0.991 (16)	O1A—H1A	1.00 (2)
C3—C4	1.3880 (18)	C2A—C2A^i	1.507 (3)
C3—H3	0.998 (18)	C2A—H2AA	0.967 (19)
C4—C5	1.3827 (18)	C2A—H2AB	0.98 (2)
C4—C7	1.5050 (17)	C7—C7^ii	1.525 (3)
C5—C6	1.3816 (18)	C7—H7A	0.982 (19)
C5—H5	0.977 (16)	C7—H7B	1.027 (19)
C6—H6	0.966 (17)
C2—N1—C6	117.59 (11)	O1A—C1A—C2A	114.56 (11)
N1—C2—C3	122.95 (12)	O2A—C1A—O1A	123.52 (12)
N1—C2—H2	116.2 (10)	O2A—C1A—C2A	121.92 (11)
C3—C2—H2	120.8 (10)	C1A—O1A—H1A	111.1 (11)
C2—C3—C4	119.56 (12)	C1A—C2A—H2AA	106.8 (11)
C2—C3—H3	119.4 (10)	C1A—C2A—H2AB	105.0 (11)
C4—C3—H3	121.0 (10)	C2A^i—C2A—C1A	115.51 (14)
C3—C4—C7	121.01 (12)	C2A^i—C2A—H2AA	111.1 (11)
C5—C4—C3	117.39 (11)	C2A^i—C2A—H2AB	111.4 (11)
C5—C4—C7	121.57 (12)	H2AA—C2A—H2AB	106.5 (15)
C4—C5—H5	121.6 (10)	C4—C7—C7^ii	111.22 (14)
C6—C5—C4	119.54 (12)	C4—C7—H7A	109.5 (10)
C6—C5—H5	118.9 (10)	C4—C7—H7B	110.0 (10)
N1—C6—C5	122.97 (12)	C7^ii—C7—H7A	106.6 (11)
N1—C6—H6	116.3 (10)	C7^ii—C7—H7B	108.5 (10)
C5—C6—H6	120.7 (10)	H7A—C7—H7B	111.0 (15)
N1—C2—C3—C4	0.4 (2)	C4—C5—C6—N1	0.5 (2)
C2—N1—C6—C5	−0.1 (2)	C5—C4—C7—C7^ii	93.58 (19)
C2—C3—C4—C5	0.1 (2)	C6—N1—C2—C3	−0.4 (2)
C2—C3—C4—C7	178.18 (13)	O1A—C1A—C2A—C2A^i	6.5 (2)
C3—C4—C5—C6	−0.5 (2)	O2A—C1A—C2A—C2A^i	−174.09 (16)
C3—C4—C7—C7^ii	−84.5 (2)	C7—C4—C5—C6	−178.63 (12)

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