Crystal design by CH⋯N and N⋯N interactions: high-pressure structures of high-nitrogen-content azido-triazolopyridazines compounds

High-nitro­gen-content compounds 6-azido-1,2,4-triazolo[4,3-b]pyridazine (C₅H₃N₇) and its 3-methyl derivative (C₆H₅N₇) have been in situ crystallized in a diamond-anvil cell and their structures determined by single-crystal X-ray diffraction. Under ambient and high-pressure conditions the crystallizations yield the same phases: the C₅H₃N₇ anhydrate and C₆H₅N₇ hydrated clathrate. In both the structures there are clearly distinguished regions of short CH⋯N and N⋯N intermolecular contacts, the latter involving exclusively the azide groups. High pressure initially increases the contents of water in the channel pores of the clathrate.

1. Introduction

Triazolopyridazine and azide groups are present in many high-nitro­gen content compounds, which are widely applied for various purposes, for example as energetic materials and active pharmaceutical ingredients (Katrusiak et al., 1996, 2005; Bałoniak & Katrusiak, 1994; Yang et al., 2015; Olejniczak et al., 2019). It is characteristic that such high-nitro­gen organic compounds have relatively high density, despite the absence of strong intermolecular contacts in their structures (Bernstein, 2002; Fabbiani & Pulham, 2006; Millar et al., 2010; Seryotkin et al., 2016; Zakharov et al., 2017; Gatta et al., 2018; Gaydamaka et al., 2019). The high density can be associated with a small content of H atoms, however, there is no systematic information about the aggregation types and intermolecular interactions. The CH groups are expected to engage in C—H⋯N hydrogen bonds, while the excess of other N atoms – potential H-atom acceptors – would either be redirected into separate regions of N⋯N contacts in the structure (Olejniczak et al., 2019) or would find H-atom donors by favoring the crystallization in the form of solvates or host–guest compounds. Varied thermodynamic conditions can significantly change the crystal structure and conformations of compounds, as well as their composition and reactivity (Fabbiani & Pulham, 2006; Boldyreva, 2008, 2014; Resnati et al., 2015). In order to provide new information about the aggregation of high-N-content molecules, we have investigated the structures of two azido-triazolopyridazine compounds: 6-azido-1,2,4-triazolo[4,3-b]pyridazine, C₅H₃N₇ (m.p. 438 K) and its methyl derivative, C₆H₅N₇ (m.p. 400 K). In the solid state both these compounds are present as the azide tautomers, although they can also transform into the tetrazole form (Fig. 1). In order to check the stability of the structures obtained under ambient conditions, we have recrystallized these two compounds under high pressure. Additionally, low temperature has been employed for comparing the effects of thermal expansion and compressibility on intermolecular contacts in C₆H₅N₇ clathrate.

Figure 1 Structural formula of 6-azido-1,2,4-triazolo[4,3-b]pyridazine (C5H3N7) and its 3-methyl derivative (C6H5N7) (left-hand view) and their tetrazole tautomer (right-hand view).

2. Experimental

High-pressure recrystallizations of compounds C₅H₃N₇ and C₆H₅N₇ were performed from the saturated acetone or aqueous solution in the diamond anvil cell (DAC) (Merrill & Bassett, 1974). Several small sample crystals were loaded to the DAC chamber, then filled with the saturated solution, because its concentration at room temperature was too low to obtain single crystals sufficiently large for X-ray diffraction measurements. After increasing the pressure all crystals were dissolved by heating the sample, so the concentration was considerably increased and then a single crystal was grown by slowly cooling the DAC.

6-Azido-1,2,4-triazolo[4,3-b]pyridazine (C₅H₃N₇): several solvents were tried for the recrystallization and the best results were obtained from acetone or aqueous solutions. Three series of experiments were performed. In the first series the acetone solution was used for growing a single crystal at 0.1 GPa and its X-ray diffraction data were collected. Then the pressure was increased in small steps under isothermal conditions and after each step the diffraction data were measured [Fig. 2(a)]. At 1.38 GPa the acetone crystallized, which hampered the further hydro­static compression. In the second series also the acetone solution was used [Fig. 2(b)], but the isochoric recrystallization was performed after each pressure increase. Above 1.20 GPa acetone crystallized. The last analogous series of experiments was carried out for the aqueous solution [Figs. 2(c)–2(d)].

Figure 2 Single crystals of C5H3N7 obtained from different high-pressure recrystallizations: (a) at 0.20 GPa (viewed in polarized light) and (b) at 0.85 GPa, both from the acetone solution; (c) at 0.14 GPa and (d) at 1.02 GPa, both from aqueous solution and viewed in polarized light.

6-Azido-3-methyl-1,2,4-triazolo[4,3-b]pyridazine (C₆H₅N₇): single crystals, large enough for X-ray diffraction, could be recrystallized only from the aqueous solution and only in the pressure range up to 0.75 GPa (Fig. 3). The methanol, acetone or ethanol solutions led to polycrystals or very small crystals. The main difficulty in obtaining a single crystal was due to persistent nucleation of other competing seeds. The crystals obtained at high pressure could be recovered after releasing the pressure (Fig. 3) and their structure was determined at ambient pressure as a function of temperature, too. The water occupancy in C₆H₅N₇·xH₂O hydrates refined to 0.3 at 0.1 MPa; to 0.4 at 0.1 MPa and from 275 K to 100 K; to 0.5 at 0.10 GPa/296 K and 0.58 GPa/296 K; and to 0.6 at 0.23 GPa/296 K.

Figure 3 Single crystals of C6H5N7·xH2O: (a) in situ crystallized from the aqueous solution at 0.10 GPa/296 K viewed in polarized light; (b) the sample recovered from the chamber after the compression to 0.74 GPa; (c) the single crystal grown at 0.23 GPa/296 K (in polarized light) and (d) the recovered sample stuck in a nylon loop.

Pressure in the DAC chamber was calibrated by the ruby-fluorescence method (Piermarini et al., 1975; Mao et al., 1985) with a Photon Control spectrometer affording an accuracy of 0.02 GPa; the calibration was performed before and after the diffraction measurements.

The crystal sample in the DAC was centered on the diffractometer by the gasket shadowing method (Budzianowski & Katrusiak, 2004). For the low-temperature measurements, an Oxford Cryosystems 700 Series attachment and SuperNova diffractometer using Cu Kα radiation and CCD plate Atlas detector were used. The high-pressure diffraction data were measured with a KUMA KM4-CCD diffractometer using Mo Kα radiation and CCD plate Eos detector. CrysAlisPro (version 171.39.46; Rigaku Oxford Diffraction, 2015) was used for recording reflections and preliminary data reduction. Reflection intensities were corrected for the DAC absorption, sample shadowing by the gasket, the sample absorption, and reflections overlapping with diamond reflections were eliminated (CrysAlisPro). OLEX2-1.2 (Dolomanov et al., 2009), SHELXL (Sheldrick, 2015a) and SHELXT (Sheldrick, 2015b) were used to solve the structures by direct methods, and to refine the models by full matrix least-squares. Anisotropic displacement factors were applied for non-hydrogen atoms. The H atoms were located from the molecular geometry, with the C—H distance equal to 0.93 Å in pyridazine and 0.97 Å in the methyl groups, and their U_iso factors constrained to 1.2 and 1.5 times U_eq of the carriers, respectively. The site occupancy factor (SOF) of the oxygen atoms of water molecules in C₆H₅N₇·xH₂O was freely refined and then fixed in the final cycles, in order to avoid the correlation between the SOF and the atomic displacement parameters. The crystal data and refinement details are summarized in Tables 1 and Tables S1–S3; the experimental and structural details have been deposited in the Cambridge Structural Database with CCDC numbers 2021837–2021846 for C₅H₃N₇ and 2021847–2021854 for C₆H₅N₇. Structural drawings have been prepared using the X-Seed interface of POV-Ray (Barbour, 2001; Persistence of Vision Raytracer, 2004) and Mercury (Macrae et al., 2020).

Table 1
Selected data of C₅H₃N₇ and C₆H₅N₇·xH₂O recrystallized from the aqueous solutions (see Tables S1–S3)

Compound	C5H3N7	C5H3N7	C6H5N7·0.3H2O	C6H5N7·0.5H2O
p (GPa)	0.14 (2)	1.40 (2)	0.0001	0.58 (2)
Space group	P21/c	P21/c	I41/a	I41/a
a (Å)	8.1016 (19)	7.7755 (16)	28.1674 (5)	27.972 (6)
b (Å)	18.473 (4)	18.017 (3)	28.1674 (5)	27.972 (6)
c (Å)	9.04 (2)	8.75 (3)	4.15209 (11)	3.9991 (8)
β (°)	95.91 (6)	93.53 (9)
Volume (Å^3)	1346 (3)	1224 (4)	3294.29 (14)	3129.1 (14)
Z, Z′	8, 2	8, 2	16, 1	16, 1
Dcalc (g cm^−3)	1.590	1.749	1.451	1.555
Final R1, wR2 (I > 2σ1)	0.0587, 0.0608	0.0775, 0.1640	0.0371, 0.1033	0.0843, 0.1658

3. Results and discussion

The crystal structures formed of molecules C₅H₃N₇ and C₆H₅N₇ are considerably different and they both are stable in all the temperature and pressure ranges investigated in this study. The C₅H₃N₇ crystal is monoclinic, with two symmetry-independent molecules (A and B). Compound C₆H₅N₇ crystallizes in the form of a tetragonal hydrated clathrate. Its structure consists of molecules CH⋯N bonded into the host framework with pores running down [z]. The pores contain strongly disordered water molecules. Different patterns of CH⋯N bonded molecules are present in the structures. It is also characteristic of the C₅H₃N₇ and C₆H₅N₇·xH₂O structures that the azide substituents group together; their shortest N⋯N intermolecular distances are 3.131 (4) Å and 3.202 (3) Å, respectively, under ambient conditions (Figs. 4 and 5).

Figure 4 The crystal structure of C5H3N7: (a) one hydrogen-bonded sheet extending along plane (10); and (b) two neighboring sheets projected along the diagonal direction [101]. The pattern of CH⋯N bonds is highlighted yellow and contacts N⋯N between the azide groups are highlighted blue. Letters A and B label independent molecules (cf. Fig. S3).

Figure 5 Structure of C6H5N7·0.5H2O at 0.58 GPa/296 K: (a) projected down [z] with the regions of CH⋯N bonds highlighted yellow, contacts N⋯N blue, and short OH⋯O, OH⋯N and CH⋯O light red (cf. Fig. S4); and (b) the [x] projection with the solvent accessible volume of the pores shown in orange, as calculated with probe radius equal 1.2 Å and grid spacing 0.1 Å.

The topology of the CH⋯N patterns is considerably different in C₅H₃N₇ and C₆H₅N₇. In C₅H₃N₇, the CH⋯N bonds link the molecules into wavy sheets with confined small regions of N⋯N contacts between azide groups, as illustrated in Fig. 4. The sheets run along crystallographic plane (10) and their `wavevector' points along [y]. Interestingly, the sheets display the crystallographic symmetry: translations [a+c] and [b], screw axis 2₁, parallel to [y]. Besides, there are pseudo-symmetries of inversion centers between molecules A and B, at the midpoints between the azide groups and at the center of the R₂²(8) ring (Etter et al., 1990) and a pseudo-glide plane n perpendicular to [y]. The most significant departure from the pseudo-inversion center is due to the inclination angle of 7.34 (9)° (at normal conditions) between molecules A located on the maxima/minima of corrugated sinusoidal sheets and molecules B located on their slopes (Fig. 4). The neighboring sheets are related by genuine inversion centers, and pairs of the sheets are related through glide planes c (cf. Fig. S1).

In C₆H₅N₇·xH₂O there are three distinct types of interaction regions (Fig. 5). The most prominent region consists of CH⋯N bonds linking the C₆H₅N₇ molecules into a three-dimensional framework. Two other regions, one consisting of contacts N⋯N and the other one potentially capable of forming bonds OH⋯O, OH⋯N and CH⋯O (the short contacts present in the structure involve disordered water molecules, for which we could not locate the H atoms in this study) are both in the form of helical columns running down 4₁ screw axes parallel to [z] in the CH⋯N bonded framework. The disordered water molecules are contained in the channel pores parallel to [z] (Fig. 5 and Fig. S2). The pores are quite wide and the water molecules can move along [z] and the crystal can change their contents, consistent with the results of high-pressure experiments described below. The voids occupy 6.5% of the crystal volume (assessed for the probing sphere of 1.2 Å in diameter) and they can accommodate spheres of maximum radius 1.66 Å; the translational parameter along these pores is quite short (a/4, see Table 1) and there are no narrow parts in the pores.

In both compounds the molecules are present in the form of azido-triazole tautomer. The shortest intermolecular contacts CH⋯N, N⋯N and CH⋯O (Fig. 6) may be associated with the main cohesion forces under ambient conditions. The Hirshfeld fingerprint plots (Fig. 6 and Fig. S5) confirm that the shortest contacts are those of CH⋯N hydrogen bonds (the spikes in the plots), while the N⋯N distances are less exposed in the central part of the fingerprints. These features are common for both independent molecules in C₅H₃N₇ and for the molecule of C₆H₅N₇·xH₂O. The N⋯N distances observed in C₅H₃N₇ and C₆H₅N₇·xH₂O are similar to those observed in both polymorphs of analogs compound 6-azido-1,2,3,4-tetrazolo[1,5-b]pyridazine (C₄H₂N₈) (Olejniczak et al., 2019), however, the topologies of CH⋯N and N⋯N regions in C₄H₂N₈ are different. In both polymorphs of C₄H₂N₈ clearly defined sheets of CH⋯N and N⋯N regions are present.

Figure 6 Hirshfeld surfaces decorated with the color scale depending on the normalized contact distances: (a) in C5H3N7 at 0.85 GPa/296 K, (b) in C6H5N7·0.6H2O at 0.23 GPa/296 K; (c) the fingerprint plots of independent C5H3N7 molecules A and B at 0.85 GPa/296 K and (d) the fingerprint plot of C6H5N7·0.6H2O molecule at 0.23 GPa/296 K (cf. Fig. S5). The surface regions forming intermolecular contacts equal to the sum of their van der Waals radii (Bondi, 1964) are white, shorter - red and longer - blue. The drawings include the neighboring molecules involved in short contacts.

The conformation of the azide groups is characteristic of the 6-substituted pyridazine rings, with the torsion angle N5—C6—N10—N11 of about 3 (3)° (molecule A) and 5 (3)° (molecule B) in C₅H₃N₇ and 4.5 (1.5)° in C₆H₅N₇·xH₂O. We have not noted any significant systematic changes in the N—N bond lengths in the azide groups, which in principle can transform between —N=N⁺=N⁻ and —N⁻—N⁺≡N configuration. Bond angle N10—N11—N12 is of about 170 (2)°, bent in the direction opposite to angle C6—N10—N11.

The intermolecular distances in C₅H₃N₇ are gradually compressed at a similar rate for CH⋯N and N⋯N contacts (Fig. S6). This result is consistent with the 2D pattern of CH⋯N bonds in the sheets, with `islands' of N⋯N interactions. The intermolecular distances CH⋯N in C₆H₅N₇·xH₂O initially increase at 0.1 GPa (Fig. S7), which is consistent with the increased volume due to the uptake of water molecules into pores.

The compression of C₅H₃N₇ is typical for a molecular crystal, monotonically reduced in size in all directions (Fig. 7 and Fig. S8). This crystal compared to C₄H₂N₈ (Olejniczak et al., 2019) is harder: compressibility β = −1/V·∂V/∂p at 0.40 GPa for phase α-C₄H₂N₈ is 0.102 GPa⁻¹ and at 0.49 GPa for phase β-C₄H₂N₈ is 0.085 GPa⁻¹ versus the compressibility of C₅H₃N₈ at 0.54 GPa equal to 0.072 GPa⁻¹. This difference can be attributed to a larger contribution of CH⋯N bonds to the cohesion forces in C₅H₃N₇ than in C₄H₂N₈.

Figure 7 Compression of the unit-cell dimensions (a) and molecular volume (b) of C5H3N7. Straight lines have been fitted to the lengths and polynomial function V = 170.20–14.31p+1.33p^2 to the volume (cf. Fig. S8). Where not indicated, the estimated standard deviations are smaller than the plotted symbols.

The compression of C₆H₅N₇·xH₂O and thermal expansion of this crystal is shown in Fig. 8 (cf. Fig. S9). The thermal expansion in all 300–100 K range is nearly linear and the volume contracts to about 97%, as expected for an average molecular crystal. The linear expansion plots along [x] and [y] are weakly convex (∂²a/∂T² is positive), while the expansion along [z] is weakly concave (∂²c/∂T² < 0). This feature corresponds to the strongly anisotropic structure, with pores parallel to [z] and perpendicular to [x] and [y].

Figure 8 Unit-cell dimensions (a) and molecular volume (b) of C6H5N7·xH2O as a function of temperature (open symbols) and pressure (full symbols). The dotted lines indicate the pressure region involving the H2O transport into the pores (cf. Fig. S9). Where not indicated, the estimated standard deviations are smaller than the plotted symbols.

The volume compressibility of C₆H₅N₇ is clearly anomalous in the 0.1 MPa to 0.1 GPa pressure region, the line fitted to the volume values measured between 0.1 and 0.58 GPa clearly points above the volume at 0.1 MPa, by about 2 ų per formula unit. This effect can be attributed to an intake of the molecules from the hydro­static medium into the pores. It is plausible that the pressure pushes additional molecules into the pores, which causes an initial increase of the crystal volume. This effect is also clearly seen in the linear compression along [x] and [y]. An average volume of one water molecule in hydrates is of about 22.8 ų (Glasser, 2019), so it can be estimated that the contents of water in C₆H₅N₇·xH₂O crystal increases by about 0.1 H₂O per formula unit. Hence the composition of the C₆H₅N₇·xH₂O crystal changes and therefore the measurements of the unit-cell dimensions as a function of pressure are not the one-compound crystal compression in the strictly physical sense. According to the X-ray diffraction data refinements in the 0.1 MPa–0.1 GPa range the x parameter in C₆H₅N₇·xH₂O changes from 0.3 to 0.6.

4. Conclusions

The increased number of H-atom donors in two high-nitro­gen-contents 6-azido-1,2,4-triazolo[4,3-b]pyridazine, (C₅H₃N₇), and its methyl derivative (C₆H₅N₇) drastically changed the topology of CH⋯N and N⋯N contacts, compared to the previously studied 6-azido-1,2,3,4-tetrazolo[1,5-b]pyridazine (C₄H₂N₈) polymorphs. The CH groups in C₅H₃N₇ and C₆H₅N₇ are effectively involved in CH⋯N bonds, binding the molecules into frameworks. It is characteristic that none of these CH⋯N bonds involve the azide groups, which form short contacts between themselves. All of these N⋯N contacts are longer than double the van der Waals radius of the nitro­gen atom. It appears that the contribution of azide groups to the cohesion forces is very weak. The strong contribution of hydrogen bonds CH⋯N to cohesion forces is supported by the formation of the porous framework in C₆H₅N₇ capable of the sorption of water under ambient and high-pressure conditions.

Supporting information

Computing details

Data collection: CrysAlis PRO 1.171.39.46 (Rigaku OD, 2018) for C5H3N7at0.14GPa, C5H3N7at0.65GPa, C5H3N7at0.85GPa, C5H3N7at1.02GPa, C5H3N7at1.40GPa, C6H5N7.H2Oat250K, C6H5N7.H2Oat200K, C6H5N7.H2Oat150K, C6H5N7.H2Oat0_10GPa, C6H5N7.H2Oat0_23GPa, C6H5N7.H2Oat0_58GPa; CrysAlis PRO, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) for C5H3N7at0.15GPa, C5H3N7at0.20GPa, C5H3N7at0.54GPa, C5H3N7at0.77GPa, C5H3N7at1.11GPa, C6H5N7.H2Oat296K, C6H5N7.H2Oat100K. Cell refinement: CrysAlis PRO 1.171.39.46 (Rigaku OD, 2018) for C5H3N7at0.14GPa, C5H3N7at0.65GPa, C5H3N7at0.85GPa, C5H3N7at1.02GPa, C5H3N7at1.40GPa, C6H5N7.H2Oat250K, C6H5N7.H2Oat200K, C6H5N7.H2Oat150K, C6H5N7.H2Oat0_10GPa, C6H5N7.H2Oat0_23GPa, C6H5N7.H2Oat0_58GPa; CrysAlis PRO, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) for C5H3N7at0.15GPa, C5H3N7at0.20GPa, C5H3N7at0.54GPa, C5H3N7at0.77GPa, C5H3N7at1.11GPa, C6H5N7.H2Oat296K, C6H5N7.H2Oat100K. Data reduction: CrysAlis PRO 1.171.39.46 (Rigaku OD, 2018) for C5H3N7at0.14GPa, C5H3N7at0.65GPa, C5H3N7at0.85GPa, C5H3N7at1.02GPa, C5H3N7at1.40GPa, C6H5N7.H2Oat250K, C6H5N7.H2Oat200K, C6H5N7.H2Oat150K, C6H5N7.H2Oat0_10GPa, C6H5N7.H2Oat0_23GPa, C6H5N7.H2Oat0_58GPa; CrysAlis PRO, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) for C5H3N7at0.15GPa, C5H3N7at0.20GPa, C5H3N7at0.54GPa, C5H3N7at0.77GPa, C5H3N7at1.11GPa, C6H5N7.H2Oat296K, C6H5N7.H2Oat100K. Program(s) used to solve structure: ShelXT (Sheldrick, 2015) for C5H3N7at0.14GPa, C5H3N7at0.77GPa, C5H3N7at0.85GPa, C5H3N7at1.02GPa, C5H3N7at1.11GPa, C5H3N7at1.40GPa, C6H5N7.H2Oat296K, C6H5N7.H2Oat250K, C6H5N7.H2Oat200K, C6H5N7.H2Oat150K, C6H5N7.H2Oat100K, C6H5N7.H2Oat0_10GPa, C6H5N7.H2Oat0_23GPa, C6H5N7.H2Oat0_58GPa; SHELXT (Sheldrick, 2015) for C5H3N7at0.15GPa, C5H3N7at0.20GPa, C5H3N7at0.54GPa; SHELXT(Sheldrick, 2015) for C5H3N7at0.65GPa. Program(s) used to refine structure: SHELXL (Sheldrick, 2015) for C5H3N7at0.14GPa, C5H3N7at0.77GPa, C5H3N7at0.85GPa, C5H3N7at1.02GPa, C5H3N7at1.11GPa, C5H3N7at1.40GPa, C6H5N7.H2Oat296K, C6H5N7.H2Oat250K, C6H5N7.H2Oat200K, C6H5N7.H2Oat150K, C6H5N7.H2Oat100K, C6H5N7.H2Oat0_10GPa, C6H5N7.H2Oat0_23GPa, C6H5N7.H2Oat0_58GPa; SHELXL 2018/3 (Sheldrick, 2015) for C5H3N7at0.15GPa, C5H3N7at0.20GPa, C5H3N7at0.54GPa, C5H3N7at0.65GPa. Molecular graphics: Olex2 (Dolomanov et al., 2009) for C5H3N7at0.14GPa, C5H3N7at0.77GPa, C5H3N7at0.85GPa, C5H3N7at1.02GPa, C5H3N7at1.11GPa, C5H3N7at1.40GPa, C6H5N7.H2Oat0_10GPa, C6H5N7.H2Oat0_23GPa, C6H5N7.H2Oat0_58GPa; Olex2 1.3 (Dolomanov et al., 2009) for C5H3N7at0.15GPa, C5H3N7at0.20GPa, C5H3N7at0.54GPa, C5H3N7at0.65GPa, C6H5N7.H2Oat296K, C6H5N7.H2Oat250K, C6H5N7.H2Oat200K, C6H5N7.H2Oat150K, C6H5N7.H2Oat100K. Software used to prepare material for publication: Olex2 (Dolomanov et al., 2009) for C5H3N7at0.14GPa, C5H3N7at0.77GPa, C5H3N7at0.85GPa, C5H3N7at1.02GPa, C5H3N7at1.11GPa, C5H3N7at1.40GPa, C6H5N7.H2Oat0_10GPa, C6H5N7.H2Oat0_23GPa, C6H5N7.H2Oat0_58GPa; Olex2 1.3 (Dolomanov et al., 2009) for C5H3N7at0.15GPa, C5H3N7at0.20GPa, C5H3N7at0.54GPa, C5H3N7at0.65GPa, C6H5N7.H2Oat296K, C6H5N7.H2Oat250K, C6H5N7.H2Oat200K, C6H5N7.H2Oat150K, C6H5N7.H2Oat100K.

6-azido-1,2,4-triazolo[4,3-b]pyridazine (C5H3N7at0.14GPa)

Crystal data

C5H3N7	F(000) = 656
Mr = 161.14	Dx = 1.590 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.1016 (19) Å	Cell parameters from 569 reflections
b = 18.473 (4) Å	θ = 4.6–18.5°
c = 9.04 (2) Å	µ = 0.12 mm^−1
β = 95.91 (6)°	T = 296 K
V = 1346 (3) Å^3	Plate, colorless
Z = 8	0.39 × 0.36 × 0.30 mm

Data collection

KM-4 CCD diffractometer	845 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	360 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.285
Detector resolution: 16.2413 pixels mm^-1	θmax = 27.2°, θmin = 4.6°
HP ω scans – for more details see: A. Budzianowski, A. Katrusiak in High–Pressure Crystallography (Eds.: A. Katrusiak, P. F. McMillan), Dordrecht: Kluwer Acad. Publ., 2004 pp.157–168	h = −10→10
Absorption correction: multi-scan CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −22→23
Tmin = 0.254, Tmax = 1.000	l = −2→2
7791 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.059	H-atom parameters constrained
wR(F^2) = 0.088	w = 1/[σ^2(Fo^2) + (0.0116P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
845 reflections	Δρmax = 0.08 e Å^−3
217 parameters	Δρmin = −0.08 e Å^−3
18 restraints

Special details

Experimental. Data were collected at room temperature and pressure of 0.14 (2) GPa (140000 kPa) with the crystal obtained by the in-situ high-pressure crystallization technique. Pressure was determined by monitoring the shift of the ruby R1-fluorescence line.

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
N24	0.6581 (7)	0.5006 (3)	0.3951 (18)	0.063 (15)
N25	0.5663 (7)	0.5557 (3)	0.326 (2)	0.052 (16)
C26	0.4604 (11)	0.5323 (4)	0.220 (3)	0.07 (3)
C27	0.4368 (9)	0.4588 (4)	0.177 (4)	0.11 (3)
H27	0.3549	0.4469	0.1009	0.131*
C28	0.5301 (10)	0.4074 (4)	0.243 (3)	0.08 (3)
H28	0.5200	0.3595	0.2118	0.098*
C29	0.6458 (10)	0.4279 (4)	0.363 (3)	0.05 (2)
N21	0.7558 (8)	0.3914 (3)	0.4515 (19)	0.085 (17)
N22	0.8372 (7)	0.4419 (4)	0.553 (2)	0.102 (19)
C23	0.7786 (9)	0.5065 (3)	0.506 (2)	0.091 (18)
H23	0.8174	0.5504	0.5464	0.109*
N210	0.3545 (7)	0.5819 (3)	0.138 (2)	0.11 (3)
N211	0.3722 (6)	0.6462 (4)	0.1818 (18)	0.077 (16)
N212	0.3721 (6)	0.7059 (3)	0.2096 (16)	0.091 (16)
N4	0.7969 (8)	0.7241 (3)	0.630 (2)	0.06 (2)
N5	0.8826 (8)	0.6702 (3)	0.707 (2)	0.047 (17)
C6	0.9942 (10)	0.6946 (4)	0.806 (3)	0.043 (14)
C7	1.0311 (7)	0.7696 (4)	0.838 (3)	0.08 (2)
H7	1.1141	0.7823	0.9127	0.098*
C8	0.9450 (10)	0.8200 (4)	0.761 (3)	0.10 (2)
H8	0.9645	0.8689	0.7803	0.115*
C9	0.8229 (11)	0.7976 (4)	0.648 (3)	0.041 (14)
N1	0.7205 (8)	0.8330 (3)	0.5524 (19)	0.089 (18)
N2	0.6263 (6)	0.7811 (3)	0.470 (3)	0.054 (14)
C3	0.6752 (9)	0.7173 (4)	0.525 (3)	0.08 (3)
H3	0.6289	0.6733	0.4920	0.093*
N10	1.0944 (7)	0.6461 (4)	0.8986 (18)	0.068 (15)
N11	1.0684 (6)	0.5809 (5)	0.864 (2)	0.110 (19)
N12	1.0629 (8)	0.5206 (3)	0.849 (2)	0.09 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N24	0.040 (4)	0.050 (4)	0.10 (5)	0.001 (3)	0.002 (8)	0.002 (7)
N25	0.051 (4)	0.046 (4)	0.05 (5)	0.004 (3)	−0.011 (7)	0.009 (7)
C26	0.049 (5)	0.058 (6)	0.09 (8)	−0.005 (4)	−0.004 (11)	0.003 (10)
C27	0.068 (5)	0.056 (6)	0.20 (8)	−0.010 (4)	−0.004 (11)	−0.011 (11)
C28	0.068 (5)	0.061 (5)	0.11 (8)	−0.006 (5)	−0.011 (14)	−0.011 (12)
C29	0.059 (6)	0.048 (5)	0.03 (8)	0.005 (4)	−0.019 (11)	0.000 (8)
N21	0.067 (4)	0.051 (3)	0.14 (5)	0.000 (3)	0.004 (10)	0.012 (8)
N22	0.064 (4)	0.065 (4)	0.17 (6)	0.004 (4)	0.001 (9)	0.017 (9)
C23	0.053 (5)	0.049 (5)	0.17 (6)	0.004 (4)	0.019 (11)	0.008 (9)
N210	0.074 (5)	0.049 (4)	0.20 (8)	−0.002 (4)	−0.029 (11)	0.010 (8)
N211	0.053 (4)	0.078 (5)	0.09 (5)	0.007 (4)	−0.017 (7)	0.015 (9)
N212	0.088 (4)	0.073 (5)	0.11 (5)	0.007 (3)	−0.006 (8)	0.005 (9)
N4	0.052 (4)	0.045 (4)	0.08 (6)	0.006 (3)	−0.013 (9)	−0.001 (7)
N5	0.051 (4)	0.059 (4)	0.03 (5)	0.002 (3)	−0.010 (9)	0.003 (8)
C6	0.049 (5)	0.064 (5)	0.02 (4)	0.002 (4)	−0.003 (11)	−0.015 (11)
C7	0.055 (5)	0.069 (5)	0.12 (7)	−0.010 (4)	0.001 (11)	−0.002 (11)
C8	0.058 (5)	0.064 (5)	0.16 (7)	−0.005 (4)	−0.023 (12)	−0.007 (12)
C9	0.067 (6)	0.041 (5)	0.01 (4)	0.001 (4)	−0.003 (12)	−0.002 (9)
N1	0.072 (4)	0.054 (4)	0.14 (6)	0.002 (3)	−0.006 (9)	0.004 (8)
N2	0.072 (4)	0.067 (4)	0.02 (4)	0.012 (3)	−0.007 (9)	−0.002 (9)
C3	0.055 (5)	0.053 (5)	0.12 (8)	0.001 (4)	−0.025 (13)	0.013 (10)
N10	0.071 (4)	0.067 (4)	0.06 (5)	0.006 (4)	−0.016 (8)	0.003 (9)
N11	0.064 (4)	0.083 (4)	0.17 (6)	0.008 (4)	−0.026 (8)	0.023 (11)
N12	0.127 (6)	0.081 (5)	0.06 (7)	0.009 (5)	−0.025 (12)	0.019 (10)

Geometric parameters (Å, º)

N24—N25	1.373 (12)	N4—N5	1.360 (13)
N24—C29	1.375 (9)	N4—C9	1.382 (8)
N24—C23	1.331 (18)	N4—C3	1.31 (2)
N25—C26	1.29 (2)	N5—C6	1.287 (17)
C26—C27	1.420 (14)	C6—C7	1.443 (10)
C26—N210	1.413 (17)	C6—N10	1.424 (17)
C27—H27	0.9300	C7—H7	0.9300
C27—C28	1.319 (17)	C7—C8	1.320 (19)
C28—H28	0.9300	C8—H8	0.9300
C28—C29	1.41 (2)	C8—C9	1.41 (2)
C29—N21	1.320 (15)	C9—N1	1.313 (17)
N21—N22	1.424 (16)	N1—N2	1.395 (14)
N22—C23	1.336 (10)	N2—C3	1.324 (10)
C23—H23	0.9300	C3—H3	0.9300
N210—N211	1.257 (10)	N10—N11	1.256 (9)
N211—N212	1.130 (9)	N11—N12	1.123 (8)
N25—N24—C29	127.2 (12)	N5—N4—C9	126.6 (10)
C23—N24—N25	127.1 (8)	C3—N4—N5	127.4 (7)
C23—N24—C29	105.7 (9)	C3—N4—C9	106.0 (8)
C26—N25—N24	112.1 (8)	C6—N5—N4	112.5 (8)
N25—C26—C27	125.8 (13)	N5—C6—C7	126.5 (10)
N25—C26—N210	119.6 (8)	N5—C6—N10	120.5 (7)
N210—C26—C27	114.6 (17)	N10—C6—C7	113.0 (12)
C26—C27—H27	119.7	C6—C7—H7	120.6
C28—C27—C26	120.6 (18)	C8—C7—C6	118.8 (15)
C28—C27—H27	119.7	C8—C7—H7	120.6
C27—C28—H28	121.3	C7—C8—H8	121.0
C27—C28—C29	117.4 (11)	C7—C8—C9	118.0 (9)
C29—C28—H28	121.3	C9—C8—H8	121.0
N24—C29—C28	116.9 (10)	N4—C9—C8	117.5 (10)
N21—C29—N24	109.9 (12)	N1—C9—N4	109.5 (10)
N21—C29—C28	133.1 (9)	N1—C9—C8	132.9 (8)
C29—N21—N22	107.2 (7)	C9—N1—N2	106.6 (8)
C23—N22—N21	104.7 (11)	C3—N2—N1	106.6 (10)
N24—C23—N22	112.1 (9)	N4—C3—N2	111.3 (8)
N24—C23—H23	124.0	N4—C3—H3	124.4
N22—C23—H23	124.0	N2—C3—H3	124.4
N211—N210—C26	113.8 (12)	N11—N10—C6	112.6 (11)
N212—N211—N210	171.8 (11)	N12—N11—N10	170.1 (14)

6-azido-1,2,4-triazolo[4,3-b]pyridazine (C5H3N7at0.15GPa)

Crystal data

C5H3N7	F(000) = 656
Mr = 161.14	Dx = 1.589 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.089 (7) Å	Cell parameters from 1039 reflections
b = 18.4614 (16) Å	θ = 4.0–20.8°
c = 9.074 (9) Å	µ = 0.12 mm^−1
β = 96.08 (11)°	T = 296 K
V = 1347.5 (19) Å^3	Plate, colorless
Z = 8	0.39 × 0.30 × 0.19 mm

Data collection

'KM-4 CCD diffractometer	506 independent reflections
Radiation source: Enhance (Mo) X-ray Source	306 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.108
Detector resolution: 16.2413 pixels mm^-1	θmax = 26.8°, θmin = 4.0°
HP ω scans – for more details see: A. Budzianowski, A. Katrusiak in High–Pressure Crystallography (Eds.: A. Katrusiak, P. F. McMillan), Dordrecht: Kluwer Acad. Publ., 2004 pp.157–168	h = −6→7
Absorption correction: multi-scan CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −22→22
Tmin = 0.663, Tmax = 1.000	l = −7→7
4953 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.073	w = 1/[σ^2(Fo^2) + (0.1573P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.234	(Δ/σ)max < 0.001
S = 1.10	Δρmax = 0.15 e Å^−3
506 reflections	Δρmin = −0.14 e Å^−3
98 parameters	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.019 (12)
Primary atom site location: structure-invariant direct methods

Special details

Experimental. Data were collected at room temperature and pressure of 0.15 (2) GPa (150000 kPa) with the crystal obtained by the in-situ high-pressure crystallization technique. Pressure was determined by monitoring the shift of the ruby R1-fluorescence line.

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
N24	0.6589 (18)	0.5008 (3)	0.3976 (19)	0.044 (2)*
N25	0.568 (2)	0.5563 (3)	0.326 (2)	0.049 (2)*
C26	0.462 (3)	0.5328 (4)	0.217 (3)	0.053 (3)*
C27	0.440 (3)	0.4591 (4)	0.173 (3)	0.061 (3)*
H27	0.363030	0.447380	0.092843	0.074*
C28	0.529 (3)	0.4071 (4)	0.244 (2)	0.060 (3)*
H28	0.518704	0.358945	0.214054	0.072*
C29	0.641 (4)	0.4287 (4)	0.369 (3)	0.052 (3)*
N21	0.754 (2)	0.3919 (3)	0.455 (2)	0.060 (2)*
N22	0.836 (2)	0.4409 (3)	0.545 (2)	0.059 (2)*
C23	0.780 (3)	0.5059 (4)	0.508 (3)	0.054 (2)*
H23	0.818722	0.548918	0.552510	0.064*
N210	0.358 (2)	0.5830 (3)	0.141 (2)	0.057 (2)*
N211	0.380 (3)	0.6470 (4)	0.177 (2)	0.062 (2)*
N212	0.382 (3)	0.7062 (4)	0.201 (3)	0.069 (3)*
N4	0.797 (2)	0.7237 (3)	0.630 (2)	0.047 (2)*
N5	0.885 (2)	0.6700 (3)	0.706 (2)	0.049 (2)*
C6	0.991 (3)	0.6946 (4)	0.811 (3)	0.052 (3)*
C7	1.033 (3)	0.7692 (4)	0.840 (3)	0.058 (3)*
H7	1.119046	0.781713	0.912041	0.070*
C8	0.945 (3)	0.8208 (4)	0.761 (3)	0.054 (3)*
H8	0.963400	0.869837	0.779930	0.064*
C9	0.824 (3)	0.7970 (4)	0.647 (3)	0.050 (3)*
N1	0.720 (2)	0.8327 (3)	0.550 (2)	0.060 (2)*
N2	0.631 (3)	0.7812 (3)	0.466 (3)	0.064 (3)*
C3	0.677 (3)	0.7176 (4)	0.518 (3)	0.050 (3)*
H3	0.632223	0.673902	0.482012	0.061*
N10	1.094 (2)	0.6449 (3)	0.895 (2)	0.054 (2)*
N11	1.072 (3)	0.5808 (3)	0.864 (3)	0.057 (2)*
N12	1.056 (3)	0.5211 (4)	0.854 (3)	0.072 (3)*

Geometric parameters (Å, º)

N24—N25	1.384 (8)	N4—N5	1.367 (8)
N24—C29	1.362 (10)	N4—C9	1.378 (9)
N24—C23	1.328 (10)	N4—C3	1.330 (10)
N25—C26	1.311 (10)	N5—C6	1.295 (10)
C26—C27	1.424 (12)	C6—C7	1.437 (11)
C26—N210	1.386 (11)	C6—N10	1.406 (9)
C27—H27	0.9300	C7—H7	0.9300
C27—C28	1.325 (10)	C7—C8	1.351 (10)
C28—H28	0.9300	C8—H8	0.9300
C28—C29	1.432 (13)	C8—C9	1.417 (10)
C29—N21	1.320 (11)	C9—N1	1.329 (9)
N21—N22	1.351 (8)	N1—N2	1.373 (10)
N22—C23	1.316 (10)	N2—C3	1.306 (9)
C23—H23	0.9300	C3—H3	0.9300
N210—N211	1.235 (8)	N10—N11	1.224 (8)
N211—N212	1.115 (9)	N11—N12	1.113 (8)
C29—N24—N25	126.5 (6)	N5—N4—C9	125.9 (6)
C23—N24—N25	128.0 (6)	C3—N4—N5	128.6 (6)
C23—N24—C29	105.6 (5)	C3—N4—C9	105.3 (6)
C26—N25—N24	112.4 (6)	C6—N5—N4	112.8 (6)
N25—C26—C27	125.5 (8)	N5—C6—C7	126.6 (8)
N25—C26—N210	117.9 (8)	N5—C6—N10	118.4 (7)
N210—C26—C27	116.5 (7)	N10—C6—C7	114.3 (7)
C26—C27—H27	119.7	C6—C7—H7	120.8
C28—C27—C26	120.6 (9)	C8—C7—C6	118.5 (8)
C28—C27—H27	119.7	C8—C7—H7	120.8
C27—C28—H28	121.6	C7—C8—H8	121.5
C27—C28—C29	116.7 (9)	C7—C8—C9	117.1 (7)
C29—C28—H28	121.6	C9—C8—H8	121.5
N24—C29—C28	118.0 (7)	N4—C9—C8	118.5 (7)
N21—C29—N24	109.7 (6)	N1—C9—N4	109.2 (6)
N21—C29—C28	131.6 (11)	N1—C9—C8	132.2 (7)
C29—N21—N22	106.4 (6)	C9—N1—N2	106.5 (6)
C23—N22—N21	108.5 (6)	C3—N2—N1	107.9 (7)
N24—C23—H23	125.1	N4—C3—H3	124.5
N22—C23—N24	109.7 (6)	N2—C3—N4	111.0 (6)
N22—C23—H23	125.1	N2—C3—H3	124.5
N211—N210—C26	116.2 (7)	N11—N10—C6	116.4 (6)
N212—N211—N210	171.5 (11)	N12—N11—N10	171.6 (19)
N24—N25—C26—C27	−1 (5)	N4—N5—C6—C7	−8 (5)
N24—N25—C26—N210	177 (2)	N4—N5—C6—N10	−178 (3)
N24—C29—N21—N22	4 (4)	N4—C9—N1—N2	−3 (3)
N25—N24—C29—C28	6 (5)	N5—N4—C9—C8	−6 (4)
N25—N24—C29—N21	177 (3)	N5—N4—C9—N1	177 (3)
N25—N24—C23—N22	−179 (3)	N5—N4—C3—N2	−175 (3)
N25—C26—C27—C28	1 (5)	N5—C6—C7—C8	7 (6)
N25—C26—N210—N211	3 (4)	N5—C6—N10—N11	−3 (4)
C26—C27—C28—C29	2 (5)	C6—C7—C8—C9	−4 (5)
C27—C26—N210—N211	−178 (3)	C7—C6—N10—N11	−174 (3)
C27—C28—C29—N24	−5 (5)	C7—C8—C9—N4	4 (4)
C27—C28—C29—N21	−174 (4)	C7—C8—C9—N1	−180 (3)
C28—C29—N21—N22	174 (4)	C8—C9—N1—N2	−180 (3)
C29—N24—N25—C26	−3 (4)	C9—N4—N5—C6	8 (4)
C29—N24—C23—N22	1 (4)	C9—N4—C3—N2	0 (3)
C29—N21—N22—C23	−3 (3)	C9—N1—N2—C3	3 (4)
N21—N22—C23—N24	2 (3)	N1—N2—C3—N4	−2 (4)
C23—N24—N25—C26	177 (3)	C3—N4—N5—C6	−178 (3)
C23—N24—C29—C28	−174 (3)	C3—N4—C9—C8	179 (3)
C23—N24—C29—N21	−3 (4)	C3—N4—C9—N1	2 (3)
N210—C26—C27—C28	−177 (3)	N10—C6—C7—C8	177 (3)

6-azido-1,2,4-triazolo[4,3-b]pyridazine (C5H3N7at0.20GPa)

Crystal data

C5H3N7	F(000) = 656
Mr = 161.14	Dx = 1.598 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.053 (16) Å	Cell parameters from 484 reflections
b = 18.470 (3) Å	θ = 4.0–26.3°
c = 9.044 (17) Å	µ = 0.12 mm^−1
β = 95.4 (2)°	T = 296 K
V = 1339 (4) Å^3	Plate, colorless
Z = 8	0.39 × 0.30 × 0.19 mm

Data collection

KM-4 CCD diffractometer	448 independent reflections
Radiation source: Enhance (Mo) X-ray Source	249 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.091
Detector resolution: 16.2413 pixels mm^-1	θmax = 26.5°, θmin = 4.0°
HP ω scans – for more details see: A. Budzianowski, A. Katrusiak in High–Pressure Crystallography (Eds.: A. Katrusiak, P. F. McMillan), Dordrecht: Kluwer Acad. Publ., 2004 pp.157–168	h = −6→6
Absorption correction: multi-scan CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −22→22
Tmin = 0.693, Tmax = 1.000	l = −7→7
2280 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.078	w = 1/[σ^2(Fo^2) + (0.155P)^2 + 0.5011P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.250	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.15 e Å^−3
448 reflections	Δρmin = −0.12 e Å^−3
98 parameters	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.02 (2)
Primary atom site location: structure-invariant direct methods

Special details

Experimental. Data were collected at room temperature and pressure of 0.20 (2) GPa (200000 kPa) with the crystal obtained by the in-situ high-pressure crystallization technique. Pressure was determined by monitoring the shift of the ruby R1-fluorescence line.

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
N24	0.656 (3)	0.5012 (4)	0.400 (3)	0.049 (3)*
N25	0.568 (3)	0.5566 (4)	0.329 (3)	0.049 (3)*
C26	0.461 (4)	0.5325 (5)	0.220 (4)	0.055 (4)*
C27	0.448 (4)	0.4596 (5)	0.167 (3)	0.061 (4)*
H27	0.380307	0.449137	0.080950	0.074*
C28	0.531 (4)	0.4071 (5)	0.240 (3)	0.061 (4)*
H28	0.514946	0.358817	0.213369	0.073*
C29	0.647 (6)	0.4282 (5)	0.363 (5)	0.054 (4)*
N21	0.750 (3)	0.3918 (4)	0.455 (3)	0.061 (3)*
N22	0.835 (3)	0.4405 (5)	0.547 (3)	0.066 (3)*
C23	0.783 (4)	0.5058 (5)	0.508 (3)	0.055 (3)*
H23	0.827280	0.548713	0.548254	0.066*
N210	0.358 (3)	0.5828 (4)	0.140 (3)	0.061 (3)*
N211	0.378 (3)	0.6468 (5)	0.177 (3)	0.063 (3)*
N212	0.387 (4)	0.7061 (5)	0.197 (4)	0.069 (4)*
N4	0.794 (3)	0.7243 (4)	0.632 (3)	0.049 (3)*
N5	0.885 (3)	0.6698 (4)	0.706 (3)	0.052 (3)*
C6	0.990 (4)	0.6951 (5)	0.810 (4)	0.058 (3)*
C7	1.034 (5)	0.7691 (5)	0.840 (4)	0.064 (4)*
H7	1.119160	0.781426	0.912124	0.077*
C8	0.948 (4)	0.8203 (5)	0.759 (4)	0.059 (4)*
H8	0.972389	0.869249	0.771812	0.071*
C9	0.817 (3)	0.7967 (4)	0.652 (3)	0.047 (3)*
N1	0.719 (4)	0.8331 (5)	0.550 (3)	0.067 (3)*
N2	0.632 (4)	0.7808 (4)	0.463 (4)	0.066 (4)*
C3	0.679 (4)	0.7172 (5)	0.517 (4)	0.053 (3)*
H3	0.637431	0.673172	0.480299	0.064*
N10	1.087 (3)	0.6451 (4)	0.903 (3)	0.064 (3)*
N11	1.064 (5)	0.5800 (5)	0.870 (4)	0.068 (4)*
N12	1.058 (4)	0.5203 (5)	0.851 (4)	0.077 (4)*

Geometric parameters (Å, º)

N24—N25	1.373 (11)	N4—N5	1.384 (11)
N24—C29	1.389 (16)	N4—C9	1.361 (10)
N24—C23	1.347 (13)	N4—C3	1.326 (14)
N25—C26	1.317 (13)	N5—C6	1.295 (13)
C26—C27	1.430 (18)	C6—C7	1.429 (15)
C26—N210	1.404 (14)	C6—N10	1.429 (13)
C27—H27	0.9300	C7—H7	0.9300
C27—C28	1.318 (12)	C7—C8	1.350 (14)
C28—H28	0.9300	C8—H8	0.9300
C28—C29	1.441 (16)	C8—C9	1.428 (13)
C29—N21	1.303 (12)	C9—N1	1.338 (12)
N21—N22	1.364 (11)	N1—N2	1.393 (14)
N22—C23	1.314 (13)	N2—C3	1.315 (12)
C23—H23	0.9300	C3—H3	0.9300
N210—N211	1.235 (11)	N10—N11	1.249 (11)
N211—N212	1.111 (10)	N11—N12	1.117 (13)
N25—N24—C29	126.8 (9)	C9—N4—N5	126.0 (8)
C23—N24—N25	128.2 (8)	C3—N4—N5	127.4 (8)
C23—N24—C29	104.6 (9)	C3—N4—C9	106.3 (8)
C26—N25—N24	111.8 (8)	C6—N5—N4	111.9 (8)
N25—C26—C27	126.1 (11)	N5—C6—C7	127.9 (10)
N25—C26—N210	118.4 (10)	N5—C6—N10	118.5 (8)
N210—C26—C27	115.3 (10)	C7—C6—N10	113.4 (9)
C26—C27—H27	119.7	C6—C7—H7	121.2
C28—C27—C26	120.5 (13)	C8—C7—C6	117.6 (11)
C28—C27—H27	119.7	C8—C7—H7	121.2
C27—C28—H28	121.6	C7—C8—H8	121.2
C27—C28—C29	116.7 (10)	C7—C8—C9	117.5 (9)
C29—C28—H28	121.6	C9—C8—H8	121.2
N24—C29—C28	117.5 (10)	N4—C9—C8	118.5 (8)
N21—C29—N24	109.6 (10)	N1—C9—N4	109.6 (8)
N21—C29—C28	132.9 (11)	N1—C9—C8	131.4 (10)
C29—N21—N22	107.4 (8)	C9—N1—N2	105.9 (8)
C23—N22—N21	108.3 (9)	C3—N2—N1	107.2 (9)
N24—C23—H23	125.1	N4—C3—H3	124.5
N22—C23—N24	109.7 (8)	N2—C3—N4	111.0 (8)
N22—C23—H23	125.1	N2—C3—H3	124.5
N211—N210—C26	115.9 (9)	N11—N10—C6	114.9 (9)
N212—N211—N210	173.2 (13)	N12—N11—N10	172.5 (14)
N24—N25—C26—C27	−7 (6)	N4—N5—C6—C7	−9 (6)
N24—N25—C26—N210	178 (4)	N4—N5—C6—N10	176 (3)
N24—C29—N21—N22	−4 (5)	N4—C9—N1—N2	0 (4)
N25—N24—C29—C28	−2 (7)	N5—N4—C9—C8	0 (5)
N25—N24—C29—N21	180 (4)	N5—N4—C9—N1	173 (3)
N25—N24—C23—N22	−180 (3)	N5—N4—C3—N2	−172 (3)
N25—C26—C27—C28	10 (7)	N5—C6—C7—C8	6 (7)
N25—C26—N210—N211	1 (5)	N5—C6—N10—N11	2 (6)
C26—C27—C28—C29	−7 (7)	C6—C7—C8—C9	1 (6)
C27—C26—N210—N211	−174 (3)	C7—C6—N10—N11	−173 (4)
C27—C28—C29—N24	3 (7)	C7—C8—C9—N4	−4 (5)
C27—C28—C29—N21	−178 (5)	C7—C8—C9—N1	−175 (4)
C28—C29—N21—N22	178 (6)	C8—C9—N1—N2	171 (4)
C29—N24—N25—C26	3 (5)	C9—N4—N5—C6	6 (5)
C29—N24—C23—N22	−7 (5)	C9—N4—C3—N2	1 (5)
C29—N21—N22—C23	−1 (5)	C9—N1—N2—C3	1 (5)
N21—N22—C23—N24	5 (5)	N1—N2—C3—N4	−1 (5)
C23—N24—N25—C26	175 (4)	C3—N4—N5—C6	178 (4)
C23—N24—C29—C28	−175 (5)	C3—N4—C9—C8	−173 (4)
C23—N24—C29—N21	7 (5)	C3—N4—C9—N1	−1 (4)
N210—C26—C27—C28	−176 (3)	N10—C6—C7—C8	−179 (4)

6-azido-1,2,4-triazolo[4,3-b]pyridazine (C5H3N7at0.54GPa)

Crystal data

C5H3N7	F(000) = 656
Mr = 161.14	Dx = 1.640 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.982 (2) Å	Cell parameters from 1140 reflections
b = 18.318 (3) Å	θ = 4.0–21.2°
c = 8.964 (2) Å	µ = 0.12 mm^−1
β = 95.08 (2)°	T = 296 K
V = 1305.6 (5) Å^3	Plate, colorless
Z = 8	0.38 × 0.30 × 0.19 mm

Data collection

KM-4 CCD diffractometer	450 independent reflections
Radiation source: Enhance (Mo) X-ray Source	286 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.100
Detector resolution: 16.2413 pixels mm^-1	θmax = 26.8°, θmin = 4.0°
HP ω scans – for more details see: A. Budzianowski, A. Katrusiak in High–Pressure Crystallography (Eds.: A. Katrusiak, P. F. McMillan), Dordrecht: Kluwer Acad. Publ., 2004 pp.157–168	h = −6→6
Absorption correction: multi-scan CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −23→22
Tmin = 0.753, Tmax = 1.000	l = −7→7
4780 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.079	w = 1/[σ^2(Fo^2) + (0.1599P)^2 + 1.8268P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.257	(Δ/σ)max < 0.001
S = 1.07	Δρmax = 0.19 e Å^−3
450 reflections	Δρmin = −0.17 e Å^−3
98 parameters	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.006 (10)
Primary atom site location: structure-invariant direct methods

Special details

Experimental. Data were collected at room temperature and pressure of 0.54 (2) GPa (540000 kPa) with the crystal obtained by the in-situ high-pressure crystallization technique. Pressure was determined by monitoring the shift of the ruby R1-fluorescence line.

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
N24	0.663 (3)	0.5007 (4)	0.393 (3)	0.039 (2)*
N25	0.562 (3)	0.5576 (4)	0.332 (3)	0.044 (3)*
C26	0.461 (4)	0.5331 (5)	0.218 (4)	0.051 (3)*
C27	0.441 (4)	0.4598 (5)	0.168 (4)	0.053 (3)*
H27	0.361372	0.448678	0.089473	0.064*
C28	0.536 (4)	0.4071 (5)	0.233 (4)	0.055 (3)*
H28	0.528823	0.359276	0.198691	0.066*
C29	0.651 (6)	0.4279 (5)	0.361 (5)	0.041 (3)*
N21	0.753 (3)	0.3908 (4)	0.453 (3)	0.058 (3)*
N22	0.837 (4)	0.4409 (4)	0.547 (3)	0.052 (3)*
C23	0.785 (4)	0.5060 (5)	0.506 (3)	0.048 (3)*
H23	0.825852	0.549546	0.548003	0.057*
N210	0.352 (3)	0.5844 (4)	0.144 (3)	0.053 (3)*
N211	0.373 (4)	0.6490 (5)	0.180 (3)	0.053 (3)*
N212	0.375 (4)	0.7084 (5)	0.204 (4)	0.066 (4)*
N4	0.789 (3)	0.7233 (4)	0.635 (3)	0.041 (2)*
N5	0.882 (3)	0.6687 (4)	0.710 (3)	0.043 (3)*
C6	0.985 (4)	0.6940 (5)	0.815 (4)	0.046 (3)*
C7	1.027 (4)	0.7690 (5)	0.846 (4)	0.049 (3)*
H7	1.109737	0.781455	0.921039	0.059*
C8	0.944 (4)	0.8214 (5)	0.761 (4)	0.052 (3)*
H8	0.967558	0.870749	0.775282	0.062*
C9	0.818 (4)	0.7969 (4)	0.649 (3)	0.042 (3)*
N1	0.717 (4)	0.8330 (4)	0.551 (3)	0.053 (3)*
N2	0.621 (4)	0.7806 (4)	0.469 (4)	0.054 (3)*
C3	0.681 (4)	0.7158 (5)	0.512 (3)	0.045 (3)*
H3	0.652776	0.671775	0.464247	0.054*
N10	1.092 (3)	0.6441 (4)	0.899 (3)	0.052 (3)*
N11	1.060 (5)	0.5789 (5)	0.874 (4)	0.055 (3)*
N12	1.055 (5)	0.5181 (5)	0.857 (4)	0.068 (4)*

Geometric parameters (Å, º)

N24—N25	1.402 (12)	N4—N5	1.381 (10)
N24—C29	1.366 (14)	N4—C9	1.372 (11)
N24—C23	1.342 (12)	N4—C3	1.346 (14)
N25—C26	1.318 (14)	N5—C6	1.286 (12)
C26—C27	1.420 (17)	C6—C7	1.434 (14)
C26—N210	1.408 (15)	C6—N10	1.417 (12)
C27—H27	0.9300	C7—H7	0.9300
C27—C28	1.329 (14)	C7—C8	1.361 (13)
C28—H28	0.9300	C8—H8	0.9300
C28—C29	1.454 (16)	C8—C9	1.428 (13)
C29—N21	1.302 (12)	C9—N1	1.318 (11)
N21—N22	1.377 (11)	N1—N2	1.398 (12)
N22—C23	1.307 (13)	N2—C3	1.325 (12)
C23—H23	0.9300	C3—H3	0.9300
N210—N211	1.235 (11)	N10—N11	1.236 (11)
N211—N212	1.109 (12)	N11—N12	1.124 (12)
C29—N24—N25	128.1 (8)	C9—N4—N5	126.1 (8)
C23—N24—N25	126.6 (10)	C3—N4—N5	126.9 (9)
C23—N24—C29	105.2 (8)	C3—N4—C9	105.5 (9)
C26—N25—N24	109.9 (11)	C6—N5—N4	112.1 (8)
N25—C26—C27	127.6 (10)	N5—C6—C7	127.6 (10)
N25—C26—N210	116.6 (12)	N5—C6—N10	118.1 (9)
N210—C26—C27	115.7 (9)	N10—C6—C7	113.5 (9)
C26—C27—H27	119.8	C6—C7—H7	120.8
C28—C27—C26	120.3 (10)	C8—C7—C6	118.4 (9)
C28—C27—H27	119.8	C8—C7—H7	120.8
C27—C28—H28	121.6	C7—C8—H8	121.7
C27—C28—C29	116.8 (12)	C7—C8—C9	116.6 (9)
C29—C28—H28	121.6	C9—C8—H8	121.7
N24—C29—C28	116.6 (8)	N4—C9—C8	118.5 (8)
N21—C29—N24	110.3 (9)	N1—C9—N4	110.2 (8)
N21—C29—C28	133.0 (11)	N1—C9—C8	131.4 (9)
C29—N21—N22	106.5 (8)	C9—N1—N2	106.3 (7)
C23—N22—N21	108.0 (8)	C3—N2—N1	107.2 (8)
N24—C23—H23	125.1	N4—C3—H3	125.2
N22—C23—N24	109.9 (8)	N2—C3—N4	109.6 (10)
N22—C23—H23	125.1	N2—C3—H3	125.2
N211—N210—C26	116.7 (8)	N11—N10—C6	115.2 (9)
N212—N211—N210	172.2 (14)	N12—N11—N10	170 (3)
N24—N25—C26—C27	5 (6)	N4—N5—C6—N10	−178 (3)
N24—N25—C26—N210	−179 (4)	N4—C9—N1—N2	−1 (4)
N24—C29—N21—N22	−1 (5)	N5—N4—C9—C8	−6 (6)
N25—N24—C29—C28	10 (7)	N5—N4—C9—N1	174 (3)
N25—N24—C29—N21	−172 (4)	N5—N4—C3—N2	−178 (4)
N25—N24—C23—N22	171 (4)	N5—C6—C7—C8	5 (8)
N25—C26—C27—C28	−3 (8)	N5—C6—N10—N11	−9 (6)
N25—C26—N210—N211	7 (6)	C6—C7—C8—C9	1 (6)
C26—C27—C28—C29	3 (7)	C6—N10—N11—N12	152 (24)
C27—C26—N210—N211	−176 (3)	C7—C6—N10—N11	−179 (4)
C27—C28—C29—N24	−6 (7)	C7—C8—C9—N4	0 (5)
C27—C28—C29—N21	176 (5)	C7—C8—C9—N1	−180 (4)
C28—C29—N21—N22	177 (6)	C8—C9—N1—N2	179 (4)
C29—N24—N25—C26	−9 (6)	C9—N4—N5—C6	11 (6)
C29—N24—C23—N22	−4 (5)	C9—N4—C3—N2	−11 (5)
C29—N21—N22—C23	−1 (4)	C9—N1—N2—C3	−6 (4)
N21—N22—C23—N24	3 (5)	N1—N2—C3—N4	11 (5)
C23—N24—N25—C26	177 (4)	C3—N4—N5—C6	174 (4)
C23—N24—C29—C28	−175 (5)	C3—N4—C9—C8	−173 (4)
C23—N24—C29—N21	3 (6)	C3—N4—C9—N1	7 (4)
N210—C26—C27—C28	−179 (3)	N10—C6—C7—C8	174 (3)
N4—N5—C6—C7	−10 (6)

6-azido-1,2,4-triazolo[4,3-b]pyridazine (C5H3N7at0.65GPa)

Crystal data

C5H3N7	F(000) = 656
Mr = 161.14	Dx = 1.655 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.965 (3) Å	Cell parameters from 884 reflections
b = 18.251 (2) Å	θ = 3.9–20.6°
c = 8.929 (7) Å	µ = 0.12 mm^−1
β = 94.85 (6)°	T = 296 K
V = 1293.3 (11) Å^3	Plate, colorless
Z = 8	0.29 × 0.12 × 0.10 mm

Data collection

KM-4 CCD diffractometer	1001 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	485 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.080
Detector resolution: 16.2413 pixels mm^-1	θmax = 27.3°, θmin = 4.0°
HP ω scans – for more details see: A. Budzianowski, A. Katrusiak in High–Pressure Crystallography (Eds.: A. Katrusiak, P. F. McMillan), Dordrecht: Kluwer Acad. Publ., 2004 pp.157–168	h = −9→9
Absorption correction: multi-scan CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −22→22
Tmin = 0.248, Tmax = 1.000	l = −7→7
6599 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.056	w = 1/[σ^2(Fo^2) + (0.0782P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.166	(Δ/σ)max < 0.001
S = 1.00	Δρmax = 0.13 e Å^−3
1001 reflections	Δρmin = −0.12 e Å^−3
218 parameters	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
6 restraints	Extinction coefficient: 0.0021 (14)
Primary atom site location: structure-invariant direct methods

Special details

Experimental. Data were collected at room temperature and pressure of 0.65 (2) GPa (650000 kPa) with the crystal obtained by the in-situ high-pressure crystallization technique. Pressure was determined by monitoring the shift of the ruby R1-fluorescence line.

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
N24	0.6584 (17)	0.5009 (5)	0.399 (3)	0.046 (13)
N25	0.5650 (16)	0.5567 (4)	0.3303 (19)	0.048 (10)
C26	0.454 (3)	0.5343 (7)	0.213 (3)	0.049 (12)
C27	0.4357 (15)	0.4605 (3)	0.1701 (18)	0.059 (10)
H27	0.358078	0.447538	0.090919	0.071*
C28	0.534 (3)	0.4064 (7)	0.246 (3)	0.093 (14)
H28	0.522512	0.357108	0.220472	0.111*
C29	0.645 (3)	0.4294 (5)	0.358 (4)	0.088 (16)
N21	0.7567 (15)	0.3909 (4)	0.4519 (17)	0.054 (8)
N22	0.8455 (16)	0.4407 (3)	0.551 (2)	0.061 (9)
C23	0.775 (2)	0.5074 (6)	0.506 (3)	0.071 (16)
H23	0.808302	0.551977	0.549682	0.085*
N210	0.3518 (11)	0.5842 (3)	0.1415 (13)	0.065 (8)
N211	0.3670 (9)	0.6490 (3)	0.1839 (12)	0.060 (7)
N212	0.3653 (10)	0.7097 (3)	0.2080 (12)	0.079 (8)
N4	0.7899 (15)	0.7229 (4)	0.630 (2)	0.043 (12)
N5	0.8785 (16)	0.6690 (5)	0.7084 (19)	0.047 (10)
C6	0.995 (2)	0.6936 (6)	0.813 (3)	0.041 (12)
C7	1.0250 (14)	0.7683 (4)	0.8437 (17)	0.063 (10)
H7	1.105735	0.781874	0.920027	0.076*
C8	0.939 (2)	0.8200 (6)	0.764 (3)	0.053 (12)
H8	0.960252	0.869507	0.782129	0.063*
C9	0.819 (3)	0.7976 (6)	0.655 (3)	0.047 (15)
N1	0.7122 (15)	0.8329 (3)	0.5505 (17)	0.067 (9)
N2	0.6224 (16)	0.7811 (3)	0.4697 (19)	0.061 (9)
C3	0.6682 (18)	0.7156 (6)	0.521 (3)	0.070 (15)
H3	0.622468	0.671374	0.485135	0.084*
N10	1.0921 (12)	0.6441 (3)	0.9007 (15)	0.082 (9)
N11	1.0677 (11)	0.5784 (3)	0.8674 (13)	0.078 (7)
N12	1.0645 (11)	0.5175 (3)	0.8508 (14)	0.099 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N24	0.054 (18)	0.045 (5)	0.04 (3)	−0.011 (7)	−0.02 (2)	−0.010 (7)
N25	0.052 (12)	0.036 (5)	0.06 (3)	0.013 (4)	0.000 (17)	0.008 (5)
C26	0.071 (17)	0.054 (7)	0.02 (3)	−0.017 (7)	−0.01 (2)	−0.007 (7)
C27	0.082 (14)	0.049 (5)	0.05 (3)	−0.008 (4)	−0.001 (17)	−0.004 (5)
C28	0.14 (2)	0.036 (6)	0.12 (3)	−0.022 (7)	0.07 (2)	−0.016 (7)
C29	0.10 (2)	0.022 (6)	0.15 (4)	0.010 (7)	0.06 (3)	0.012 (8)
N21	0.060 (11)	0.048 (4)	0.05 (2)	−0.008 (5)	−0.017 (15)	−0.011 (5)
N22	0.062 (11)	0.062 (5)	0.06 (2)	0.003 (4)	−0.013 (16)	0.016 (5)
C23	0.087 (19)	0.038 (5)	0.09 (4)	0.002 (7)	0.03 (3)	0.003 (7)
N210	0.087 (11)	0.044 (4)	0.06 (2)	−0.001 (4)	−0.006 (14)	0.005 (4)
N211	0.051 (9)	0.061 (4)	0.07 (2)	0.003 (3)	0.001 (13)	0.010 (4)
N212	0.092 (10)	0.060 (4)	0.09 (2)	0.002 (3)	0.015 (13)	0.003 (4)
N4	0.052 (16)	0.040 (5)	0.03 (3)	−0.002 (5)	−0.01 (2)	−0.003 (5)
N5	0.069 (14)	0.043 (5)	0.03 (2)	0.008 (5)	−0.001 (17)	0.011 (5)
C6	0.045 (17)	0.055 (7)	0.02 (3)	0.000 (6)	−0.02 (2)	−0.010 (7)
C7	0.082 (13)	0.056 (5)	0.05 (3)	0.005 (5)	0.013 (17)	0.009 (5)
C8	0.073 (16)	0.052 (5)	0.03 (3)	−0.017 (7)	0.00 (2)	−0.018 (7)
C9	0.06 (2)	0.035 (6)	0.04 (4)	0.005 (7)	0.00 (3)	0.004 (7)
N1	0.079 (13)	0.042 (4)	0.08 (2)	0.001 (5)	0.009 (16)	0.000 (6)
N2	0.080 (12)	0.048 (5)	0.05 (2)	0.017 (4)	−0.008 (15)	0.013 (4)
C3	0.064 (17)	0.049 (6)	0.10 (4)	−0.006 (7)	0.01 (2)	−0.006 (8)
N10	0.106 (12)	0.045 (4)	0.10 (2)	0.003 (4)	0.025 (16)	−0.007 (4)
N11	0.092 (9)	0.058 (3)	0.088 (18)	0.009 (3)	0.037 (12)	0.012 (4)
N12	0.130 (10)	0.054 (3)	0.12 (2)	0.003 (4)	0.029 (14)	0.015 (4)

Geometric parameters (Å, º)

N24—N25	1.37 (3)	N4—N5	1.37 (3)
N24—C29	1.356 (17)	N4—C9	1.397 (15)
N24—C23	1.28 (4)	N4—C3	1.33 (4)
N25—C26	1.38 (4)	N5—C6	1.34 (3)
C26—C27	1.402 (14)	C6—C7	1.408 (14)
C26—N210	1.34 (3)	C6—N10	1.39 (3)
C27—H27	0.9300	C7—H7	0.9300
C27—C28	1.40 (3)	C7—C8	1.33 (3)
C28—H28	0.9300	C8—H8	0.9300
C28—C29	1.35 (5)	C8—C9	1.37 (4)
C29—N21	1.36 (4)	C9—N1	1.37 (3)
N21—N22	1.41 (2)	N1—N2	1.36 (2)
N22—C23	1.38 (2)	N2—C3	1.32 (2)
C23—H23	0.9300	C3—H3	0.9300
N210—N211	1.244 (8)	N10—N11	1.245 (9)
N211—N212	1.128 (6)	N11—N12	1.121 (6)
C29—N24—N25	125 (2)	N5—N4—C9	123 (2)
C23—N24—N25	126.5 (13)	C3—N4—N5	128.2 (11)
C23—N24—C29	109 (2)	C3—N4—C9	109 (2)
N24—N25—C26	114.1 (10)	C6—N5—N4	114.4 (12)
N25—C26—C27	122 (2)	N5—C6—C7	124 (2)
N210—C26—N25	118.9 (11)	N5—C6—N10	119.8 (11)
N210—C26—C27	119 (2)	N10—C6—C7	117 (2)
C26—C27—H27	119.8	C6—C7—H7	119.6
C28—C27—C26	120 (2)	C8—C7—C6	120.8 (19)
C28—C27—H27	119.8	C8—C7—H7	119.6
C27—C28—H28	121.8	C7—C8—H8	121.2
C29—C28—C27	116.4 (12)	C7—C8—C9	117.6 (12)
C29—C28—H28	121.8	C9—C8—H8	121.2
N24—C29—N21	107 (3)	C8—C9—N4	120 (2)
C28—C29—N24	122 (3)	C8—C9—N1	134.5 (15)
C28—C29—N21	130.5 (13)	N1—C9—N4	105 (2)
C29—N21—N22	108.5 (10)	N2—N1—C9	107.7 (9)
C23—N22—N21	102.5 (18)	C3—N2—N1	109.3 (19)
N24—C23—N22	112.6 (13)	N4—C3—H3	125.5
N24—C23—H23	123.7	N2—C3—N4	109.1 (13)
N22—C23—H23	123.7	N2—C3—H3	125.5
N211—N210—C26	117.5 (12)	N11—N10—C6	115.1 (14)
N212—N211—N210	171.1 (10)	N12—N11—N10	170.5 (11)
N24—N25—C26—C27	1.6 (16)	N4—N5—C6—C7	0.4 (16)
N24—N25—C26—N210	177.6 (8)	N4—N5—C6—N10	179.5 (7)
N24—C29—N21—N22	−1.6 (11)	N4—C9—N1—N2	1.0 (10)
N25—N24—C29—C28	−1 (2)	N5—N4—C9—C8	−1.4 (18)
N25—N24—C29—N21	−179.8 (11)	N5—N4—C9—N1	176.9 (9)
N25—N24—C23—N22	180.0 (7)	N5—N4—C3—N2	−176.5 (7)
N25—C26—C27—C28	−0.9 (14)	N5—C6—C7—C8	−1.7 (15)
N25—C26—N210—N211	1.9 (13)	N5—C6—N10—N11	3.6 (12)
C26—C27—C28—C29	−0.8 (13)	C6—C7—C8—C9	1.4 (13)
C27—C26—N210—N211	178.1 (7)	C7—C6—N10—N11	−177.2 (6)
C27—C28—C29—N24	1.8 (19)	C7—C8—C9—N4	0.1 (16)
C27—C28—C29—N21	−179.9 (8)	C7—C8—C9—N1	−177.6 (9)
C28—C29—N21—N22	179.9 (12)	C8—C9—N1—N2	178.9 (12)
C29—N24—N25—C26	−0.6 (18)	C9—N4—N5—C6	1.1 (16)
C29—N24—C23—N22	−2 (3)	C9—N4—C3—N2	2 (2)
C29—N21—N22—C23	0.4 (11)	C9—N1—N2—C3	0.5 (10)
N21—N22—C23—N24	1 (2)	N1—N2—C3—N4	−1.8 (17)
C23—N24—N25—C26	177 (2)	C3—N4—N5—C6	179.8 (17)
C23—N24—C29—C28	−179.1 (16)	C3—N4—C9—C8	179.7 (13)
C23—N24—C29—N21	2 (2)	C3—N4—C9—N1	−2.0 (17)
N210—C26—C27—C28	−176.9 (8)	N10—C6—C7—C8	179.1 (7)

6-azido-1,2,4-triazolo[4,3-b]pyridazine (C5H3N7at0.77GPa)

Crystal data

C5H3N7	F(000) = 656
Mr = 161.14	Dx = 1.673 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.918 (15) Å	Cell parameters from 890 reflections
b = 18.223 (2) Å	θ = 4.1–21.3°
c = 8.897 (14) Å	µ = 0.12 mm^−1
β = 94.6 (2)°	T = 296 K
V = 1280 (3) Å^3	Plate, colorless
Z = 8	0.36 × 0.29 × 0.18 mm

Data collection

KM-4 CCD diffractometer	438 independent reflections
Radiation source: Enhance (Mo) X-ray Source	267 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.160
Detector resolution: 16.2413 pixels mm^-1	θmax = 26.9°, θmin = 4.1°
HP ω scans – for more details see: A. Budzianowski, A. Katrusiak in High–Pressure Crystallography (Eds.: A. Katrusiak, P. F. McMillan), Dordrecht: Kluwer Acad. Publ., 2004 pp.157–168	h = −6→6
Absorption correction: multi-scan CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −23→22
Tmin = 0.734, Tmax = 1.000	l = −7→8
4666 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.071	w = 1/[σ^2(Fo^2) + (0.155P)^2 + 0.2012P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.231	(Δ/σ)max < 0.001
S = 1.08	Δρmax = 0.13 e Å^−3
438 reflections	Δρmin = −0.14 e Å^−3
98 parameters	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.015 (11)
Primary atom site location: structure-invariant direct methods

Special details

Experimental. Data were collected at room temperature and pressure of 0.77 (2) GPa (770000 kPa) with the crystal obtained by the in-situ high-pressure crystallization technique. Pressure was determined by monitoring the shift of the ruby R1-fluorescence line.

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
N24	0.657 (3)	0.5011 (3)	0.400 (3)	0.040 (2)*
N25	0.563 (3)	0.5576 (3)	0.329 (3)	0.040 (2)*
C26	0.459 (4)	0.5350 (4)	0.218 (3)	0.046 (3)*
C27	0.442 (3)	0.4598 (4)	0.167 (3)	0.057 (3)*
H27	0.3692	0.4486	0.0828	0.069*
C28	0.530 (3)	0.4071 (4)	0.239 (3)	0.047 (3)*
H28	0.5170	0.3583	0.2095	0.057*
C29	0.645 (5)	0.4275 (4)	0.365 (4)	0.041 (3)*
N21	0.751 (3)	0.3901 (3)	0.457 (2)	0.049 (2)*
N22	0.840 (3)	0.4409 (4)	0.543 (3)	0.053 (3)*
C23	0.782 (3)	0.5059 (4)	0.512 (3)	0.044 (3)*
H23	0.8195	0.5490	0.5598	0.053*
N210	0.348 (3)	0.5851 (3)	0.143 (2)	0.048 (2)*
N211	0.369 (3)	0.6497 (4)	0.180 (3)	0.053 (3)*
N212	0.372 (4)	0.7103 (4)	0.207 (3)	0.057 (3)*
N4	0.788 (3)	0.7228 (3)	0.635 (3)	0.039 (2)*
N5	0.881 (3)	0.6676 (3)	0.709 (2)	0.041 (2)*
C6	0.990 (4)	0.6930 (5)	0.813 (3)	0.045 (3)*
C7	1.027 (4)	0.7688 (4)	0.848 (3)	0.053 (3)*
H7	1.1097	0.7815	0.9240	0.064*
C8	0.937 (4)	0.8212 (5)	0.767 (3)	0.047 (3)*
H8	0.9587	0.8709	0.7836	0.057*
C9	0.810 (3)	0.7972 (4)	0.657 (3)	0.036 (3)*
N1	0.716 (3)	0.8322 (4)	0.549 (3)	0.048 (2)*
N2	0.623 (3)	0.7801 (4)	0.466 (3)	0.056 (3)*
C3	0.672 (4)	0.7155 (4)	0.519 (3)	0.045 (3)*
H3	0.6318	0.6708	0.4806	0.054*
N10	1.095 (3)	0.6436 (4)	0.897 (2)	0.050 (2)*
N11	1.074 (5)	0.5774 (4)	0.862 (4)	0.055 (3)*
N12	1.057 (4)	0.5159 (4)	0.854 (3)	0.061 (3)*

Geometric parameters (Å, º)

N24—N25	1.390 (9)	N4—N5	1.381 (9)
N24—C29	1.378 (13)	N4—C9	1.380 (9)
N24—C23	1.354 (11)	N4—C3	1.331 (12)
N25—C26	1.300 (11)	N5—C6	1.301 (11)
C26—C27	1.446 (16)	C6—C7	1.441 (12)
C26—N210	1.398 (13)	C6—N10	1.400 (10)
C27—C28	1.322 (11)	C7—C8	1.363 (11)
C28—C29	1.434 (13)	C8—C9	1.417 (11)
C29—N21	1.314 (10)	C9—N1	1.333 (11)
N21—N22	1.366 (9)	N1—N2	1.375 (11)
N22—C23	1.294 (13)	N2—C3	1.317 (10)
N210—N211	1.231 (10)	N10—N11	1.253 (11)
N211—N212	1.131 (10)	N11—N12	1.130 (9)
C29—N24—N25	126.5 (7)	C9—N4—N5	126.3 (6)
C23—N24—N25	128.3 (7)	C3—N4—N5	127.1 (7)
C23—N24—C29	105.1 (7)	C3—N4—C9	106.1 (6)
C26—N25—N24	113.0 (8)	C6—N5—N4	112.2 (6)
N25—C26—C27	125.2 (9)	N5—C6—C7	127.4 (8)
N25—C26—N210	119.4 (10)	N5—C6—N10	118.9 (8)
N210—C26—C27	115.4 (7)	N10—C6—C7	113.6 (7)
C28—C27—C26	120.3 (9)	C8—C7—C6	118.0 (9)
C27—C28—C29	117.8 (9)	C7—C8—C9	117.5 (8)
N24—C29—C28	117.1 (7)	N4—C9—C8	118.4 (7)
N21—C29—N24	109.7 (8)	N1—C9—N4	108.2 (7)
N21—C29—C28	133.2 (10)	N1—C9—C8	132.8 (8)
C29—N21—N22	106.1 (6)	C9—N1—N2	107.5 (6)
C23—N22—N21	109.7 (7)	C3—N2—N1	107.2 (7)
N22—C23—N24	109.2 (8)	N2—C3—N4	110.8 (7)
N211—N210—C26	115.5 (7)	N11—N10—C6	115.1 (7)
N212—N211—N210	173.1 (14)	N12—N11—N10	169 (3)

6-azido-1,2,4-triazolo[4,3-b]pyridazine (C5H3N7at0.85GPa)

Crystal data

C5H3N7	F(000) = 656
Mr = 161.14	Dx = 1.688 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.897 (2) Å	Cell parameters from 843 reflections
b = 18.1579 (18) Å	θ = 4.0–24.2°
c = 8.874 (5) Å	µ = 0.12 mm^−1
β = 94.54 (5)°	T = 296 K
V = 1268.5 (8) Å^3	Plate, colorless
Z = 8	0.27 × 0.20 × 0.10 mm

Data collection

KM-4 CCD diffractometer	848 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	461 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.078
Detector resolution: 16.2413 pixels mm^-1	θmax = 27.4°, θmin = 4.0°
HP ω scans – for more details see: A. Budzianowski, A. Katrusiak in High–Pressure Crystallography (Eds.: A. Katrusiak, P. F. McMillan), Dordrecht: Kluwer Acad. Publ., 2004 pp.157–168	h = −9→8
Absorption correction: multi-scan CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −22→22
Tmin = 0.698, Tmax = 1.000	l = −7→7
5632 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.039	H-atom parameters constrained
wR(F^2) = 0.070	w = 1/[σ^2(Fo^2) + (0.0177P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.98	(Δ/σ)max < 0.001
848 reflections	Δρmax = 0.10 e Å^−3
217 parameters	Δρmin = −0.11 e Å^−3
0 restraints

Special details

Experimental. Data were collected at room temperature and pressure of 0.85 (2) GPa (850000 kPa) with the crystal obtained by the in-situ high-pressure crystallization technique. Pressure was determined by monitoring the shift of the ruby R1-fluorescence line.

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
N24	0.6609 (14)	0.5012 (4)	0.404 (3)	0.063 (13)
N25	0.5603 (17)	0.5588 (4)	0.325 (2)	0.071 (10)
C26	0.465 (3)	0.5338 (6)	0.227 (3)	0.070 (13)
C27	0.4330 (14)	0.4604 (3)	0.1679 (16)	0.063 (10)
H27	0.3549	0.4495	0.0870	0.076*
C28	0.536 (2)	0.4065 (6)	0.249 (3)	0.056 (11)
H28	0.5258	0.3568	0.2251	0.067*
C29	0.646 (3)	0.4287 (5)	0.358 (3)	0.073 (14)
N21	0.7543 (13)	0.3902 (3)	0.4456 (15)	0.077 (9)
N22	0.8440 (13)	0.4403 (2)	0.5499 (15)	0.069 (8)
C23	0.7791 (17)	0.5066 (7)	0.503 (3)	0.073 (15)
H23	0.8196	0.5514	0.5422	0.087*
N210	0.3506 (10)	0.5844 (2)	0.1416 (12)	0.050 (8)
N211	0.3653 (8)	0.6506 (2)	0.1851 (10)	0.045 (7)
N212	0.3628 (8)	0.71083 (19)	0.2108 (9)	0.053 (7)
N4	0.7880 (16)	0.7217 (4)	0.631 (2)	0.052 (12)
N5	0.8802 (15)	0.6678 (4)	0.7136 (17)	0.044 (9)
C6	0.991 (2)	0.6934 (6)	0.813 (3)	0.059 (13)
C7	1.0229 (13)	0.7687 (3)	0.8436 (16)	0.077 (10)
H7	1.1037	0.7823	0.9205	0.092*
C8	0.937 (2)	0.8205 (6)	0.762 (2)	0.059 (11)
H8	0.9602	0.8704	0.7760	0.071*
C9	0.817 (2)	0.7977 (5)	0.659 (3)	0.062 (14)
N1	0.7126 (15)	0.8326 (3)	0.5550 (17)	0.077 (9)
N2	0.6153 (14)	0.7807 (2)	0.4664 (16)	0.055 (8)
C3	0.6673 (17)	0.7152 (6)	0.524 (3)	0.067 (15)
H3	0.6221	0.6703	0.4903	0.080*
N10	1.0898 (10)	0.6431 (3)	0.9007 (12)	0.060 (9)
N11	1.0690 (8)	0.5768 (2)	0.8705 (10)	0.064 (7)
N12	1.0644 (8)	0.51574 (18)	0.8519 (9)	0.060 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N24	0.045 (17)	0.035 (5)	0.11 (3)	0.002 (6)	0.03 (2)	0.012 (7)
N25	0.086 (13)	0.024 (4)	0.11 (2)	0.004 (4)	0.044 (17)	0.010 (5)
C26	0.088 (18)	0.026 (6)	0.10 (3)	−0.010 (6)	0.05 (2)	−0.007 (6)
C27	0.068 (13)	0.047 (5)	0.08 (2)	0.000 (4)	0.014 (17)	0.012 (4)
C28	0.058 (15)	0.032 (5)	0.08 (3)	−0.012 (6)	0.016 (18)	−0.004 (7)
C29	0.10 (2)	0.013 (5)	0.12 (3)	−0.009 (7)	0.06 (3)	−0.012 (7)
N21	0.081 (11)	0.035 (3)	0.12 (2)	−0.001 (4)	0.038 (15)	−0.012 (5)
N22	0.073 (10)	0.047 (4)	0.09 (2)	0.000 (3)	0.013 (14)	−0.003 (4)
C23	0.056 (16)	0.043 (4)	0.12 (4)	0.000 (6)	0.03 (2)	0.007 (6)
N210	0.054 (11)	0.043 (4)	0.048 (19)	−0.004 (3)	−0.022 (13)	0.001 (3)
N211	0.041 (8)	0.058 (3)	0.036 (18)	0.007 (2)	−0.009 (12)	0.015 (3)
N212	0.053 (9)	0.056 (3)	0.045 (17)	0.012 (2)	−0.022 (12)	0.008 (3)
N4	0.050 (17)	0.042 (5)	0.07 (3)	0.003 (6)	0.02 (2)	0.004 (7)
N5	0.051 (12)	0.035 (4)	0.04 (2)	0.019 (4)	−0.002 (15)	0.018 (5)
C6	0.057 (18)	0.045 (6)	0.08 (3)	−0.013 (6)	0.02 (2)	−0.013 (7)
C7	0.089 (14)	0.041 (4)	0.11 (2)	0.002 (4)	0.052 (17)	0.003 (5)
C8	0.049 (15)	0.042 (5)	0.09 (3)	−0.015 (5)	0.016 (18)	−0.007 (6)
C9	0.06 (2)	0.020 (5)	0.11 (3)	0.007 (6)	0.04 (3)	0.005 (6)
N1	0.072 (12)	0.041 (3)	0.12 (2)	−0.004 (5)	0.034 (15)	−0.001 (6)
N2	0.052 (11)	0.053 (5)	0.06 (2)	0.010 (3)	−0.006 (14)	0.012 (4)
C3	0.053 (18)	0.043 (5)	0.11 (4)	0.004 (6)	0.01 (2)	0.007 (7)
N10	0.073 (12)	0.044 (3)	0.06 (2)	0.000 (3)	0.003 (15)	−0.010 (4)
N11	0.079 (9)	0.051 (3)	0.063 (16)	0.006 (3)	0.023 (12)	0.003 (3)
N12	0.080 (8)	0.049 (2)	0.049 (16)	0.005 (2)	−0.019 (11)	0.009 (3)

Geometric parameters (Å, º)

N24—N25	1.46 (3)	N4—N5	1.39 (3)
N24—C29	1.381 (15)	N4—C9	1.417 (14)
N24—C23	1.24 (4)	N4—C3	1.30 (4)
N25—C26	1.20 (4)	N5—C6	1.28 (3)
C26—C27	1.445 (14)	C6—C7	1.412 (12)
C26—N210	1.46 (3)	C6—N10	1.40 (3)
C27—H27	0.9300	C7—H7	0.9300
C27—C28	1.43 (3)	C7—C8	1.34 (2)
C28—H28	0.9300	C8—H8	0.9300
C28—C29	1.31 (5)	C8—C9	1.33 (4)
C29—N21	1.31 (4)	C9—N1	1.35 (3)
N21—N22	1.44 (2)	N1—N2	1.42 (2)
N22—C23	1.36 (2)	N2—C3	1.34 (2)
C23—H23	0.9300	C3—H3	0.9300
N210—N211	1.265 (7)	N10—N11	1.240 (6)
N211—N212	1.117 (4)	N11—N12	1.122 (4)
C29—N24—N25	121 (2)	N5—N4—C9	122 (2)
C23—N24—N25	129.6 (13)	C3—N4—N5	130.1 (12)
C23—N24—C29	109.2 (19)	C3—N4—C9	108.4 (18)
C26—N25—N24	111.5 (13)	C6—N5—N4	114.1 (11)
N25—C26—C27	134 (3)	N5—C6—C7	126 (2)
N25—C26—N210	117.9 (11)	N5—C6—N10	117.9 (11)
C27—C26—N210	108 (2)	N10—C6—C7	116 (2)
C26—C27—H27	124.0	C6—C7—H7	120.0
C28—C27—C26	111.9 (19)	C8—C7—C6	120.1 (18)
C28—C27—H27	124.0	C8—C7—H7	120.0
C27—C28—H28	120.7	C7—C8—H8	121.4
C29—C28—C27	118.6 (13)	C9—C8—C7	117.1 (11)
C29—C28—H28	120.7	C9—C8—H8	121.4
C28—C29—N24	123 (3)	C8—C9—N4	121 (2)
C28—C29—N21	129.5 (12)	C8—C9—N1	133.4 (14)
N21—C29—N24	107 (3)	N1—C9—N4	105 (2)
C29—N21—N22	108.0 (9)	C9—N1—N2	110.1 (8)
C23—N22—N21	102.0 (15)	C3—N2—N1	104.0 (16)
N24—C23—N22	113.0 (13)	N4—C3—N2	112.5 (12)
N24—C23—H23	123.5	N4—C3—H3	123.8
N22—C23—H23	123.5	N2—C3—H3	123.8
N211—N210—C26	113.8 (12)	N11—N10—C6	117.1 (12)
N212—N211—N210	171.7 (9)	N12—N11—N10	173.2 (9)

6-azido-1,2,4-triazolo[4,3-b]pyridazine (C5H3N7at1.02GPa)

Crystal data

C5H3N7	F(000) = 656
Mr = 161.14	Dx = 1.708 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.8356 (16) Å	Cell parameters from 384 reflections
b = 18.074 (3) Å	θ = 4.3–18.9°
c = 8.88 (3) Å	µ = 0.13 mm^−1
β = 94.24 (7)°	T = 296 K
V = 1253 (4) Å^3	Plate, colorless
Z = 8	0.35 × 0.28 × 0.17 mm

Data collection

KM-4 CCD diffractometer	544 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	269 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.238
Detector resolution: 16.2413 pixels mm^-1	θmax = 27.0°, θmin = 4.3°
HP ω scans – for more details see: A. Budzianowski, A. Katrusiak in High–Pressure Crystallography (Eds.: A. Katrusiak, P. F. McMillan), Dordrecht: Kluwer Acad. Publ., 2004 pp.157–168	h = −9→9
Absorption correction: multi-scan CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −22→22
Tmin = 0.692, Tmax = 1.000	l = −2→2
5110 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.076	H-atom parameters constrained
wR(F^2) = 0.198	w = 1/[σ^2(Fo^2) + (0.0821P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max < 0.001
544 reflections	Δρmax = 0.14 e Å^−3
97 parameters	Δρmin = −0.13 e Å^−3
0 restraints

Special details

Experimental. Data were collected at room temperature and pressure of 1.02 (2) GPa (1020000 kPa) with the crystal obtained by the in-situ high-pressure crystallization technique. Pressure was determined by monitoring the shift of the ruby R1-fluorescence line.

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
N24	0.6583 (10)	0.5011 (4)	0.398 (3)	0.040 (2)*
N25	0.5657 (10)	0.5583 (4)	0.326 (3)	0.044 (2)*
C26	0.4579 (14)	0.5347 (5)	0.214 (5)	0.051 (3)*
C27	0.4363 (14)	0.4604 (5)	0.169 (4)	0.056 (3)*
H27	0.3551	0.4483	0.0913	0.067*
C28	0.5305 (13)	0.4078 (5)	0.237 (4)	0.052 (3)*
H28	0.5194	0.3588	0.2058	0.062*
C29	0.6463 (12)	0.4277 (5)	0.356 (4)	0.040 (3)*
N21	0.7555 (10)	0.3899 (4)	0.451 (3)	0.047 (2)*
N22	0.8402 (10)	0.4400 (4)	0.553 (3)	0.057 (3)*
C23	0.7814 (13)	0.5062 (5)	0.506 (4)	0.048 (3)*
H23	0.8230	0.5509	0.5463	0.057*
N210	0.3490 (10)	0.5858 (4)	0.144 (3)	0.053 (3)*
N211	0.3635 (10)	0.6507 (5)	0.187 (3)	0.056 (3)*
N212	0.3624 (10)	0.7112 (5)	0.213 (3)	0.065 (3)*
N4	0.7879 (10)	0.7215 (4)	0.637 (3)	0.045 (2)*
N5	0.8756 (10)	0.6673 (4)	0.723 (4)	0.049 (3)*
C6	0.9919 (13)	0.6926 (5)	0.815 (5)	0.046 (3)*
C7	1.0235 (12)	0.7688 (5)	0.847 (4)	0.053 (3)*
H7	1.1082	0.7819	0.9215	0.064*
C8	0.9356 (13)	0.8201 (5)	0.775 (5)	0.046 (3)*
H8	0.9523	0.8699	0.7977	0.055*
C9	0.8136 (12)	0.7969 (4)	0.659 (4)	0.040 (3)*
N1	0.7108 (10)	0.8315 (4)	0.549 (3)	0.055 (3)*
N2	0.6163 (10)	0.7801 (4)	0.473 (4)	0.053 (3)*
C3	0.6634 (12)	0.7138 (5)	0.519 (5)	0.047 (3)*
H3	0.6206	0.6693	0.4796	0.057*
N10	1.0910 (11)	0.6431 (4)	0.899 (4)	0.057 (3)*
N11	1.0703 (11)	0.5772 (5)	0.867 (4)	0.064 (3)*
N12	1.0658 (11)	0.5155 (5)	0.844 (4)	0.075 (3)*

Geometric parameters (Å, º)

N24—N25	1.393 (16)	N4—N5	1.39 (2)
N24—C29	1.382 (14)	N4—C9	1.390 (11)
N24—C23	1.31 (3)	N4—C3	1.38 (4)
N25—C26	1.33 (3)	N5—C6	1.26 (2)
C26—C27	1.406 (18)	C6—C7	1.426 (14)
C26—N210	1.37 (2)	C6—N10	1.37 (3)
C27—C28	1.32 (2)	C7—C8	1.30 (2)
C28—C29	1.39 (3)	C8—C9	1.41 (4)
C29—N21	1.35 (2)	C9—N1	1.37 (3)
N21—N22	1.41 (2)	N1—N2	1.338 (18)
N22—C23	1.336 (15)	N2—C3	1.310 (13)
N210—N211	1.237 (15)	N10—N11	1.231 (12)
N211—N212	1.118 (12)	N11—N12	1.135 (13)
C29—N24—N25	124.2 (16)	C9—N4—N5	123.3 (15)
C23—N24—N25	128.1 (9)	C3—N4—N5	129.5 (10)
C23—N24—C29	107.4 (10)	C3—N4—C9	107.2 (10)
C26—N25—N24	113.0 (10)	C6—N5—N4	113.9 (10)
N25—C26—C27	125.1 (17)	N5—C6—C7	125.9 (13)
N25—C26—N210	117.5 (13)	N5—C6—N10	117.9 (10)
N210—C26—C27	117 (2)	N10—C6—C7	116.0 (18)
C28—C27—C26	120 (2)	C8—C7—C6	121 (2)
C27—C28—C29	118.2 (14)	C7—C8—C9	117.0 (13)
N24—C29—C28	118.9 (12)	N4—C9—C8	118.6 (12)
N21—C29—N24	106.7 (16)	N1—C9—N4	105.7 (14)
N21—C29—C28	134.3 (10)	N1—C9—C8	135.6 (9)
C29—N21—N22	108.9 (10)	N2—N1—C9	108.5 (11)
C23—N22—N21	104.1 (17)	C3—N2—N1	110.2 (13)
N24—C23—N22	112.4 (12)	N2—C3—N4	108.1 (10)
N211—N210—C26	117.2 (18)	N11—N10—C6	116.7 (18)
N212—N211—N210	171.9 (19)	N12—N11—N10	173.7 (13)

6-azido-1,2,4-triazolo[4,3-b]pyridazine (C5H3N7at1.11GPa)

Crystal data

C5H3N7	F(000) = 656
Mr = 161.14	Dx = 1.715 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.840 (12) Å	Cell parameters from 786 reflections
b = 18.094 (2) Å	θ = 4.1–20.6°
c = 8.820 (11) Å	µ = 0.13 mm^−1
β = 94.13 (16)°	T = 296 K
V = 1248 (2) Å^3	Plate, colorless
Z = 8	0.35 × 0.27 × 0.16 mm

Data collection

KM-4 CCD diffractometer	433 independent reflections
Radiation source: Enhance (Mo) X-ray Source	269 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.139
Detector resolution: 16.2413 pixels mm^-1	θmax = 26.9°, θmin = 4.1°
HP ω scans – for more details see: A. Budzianowski, A. Katrusiak in High–Pressure Crystallography (Eds.: A. Katrusiak, P. F. McMillan), Dordrecht: Kluwer Acad. Publ., 2004 pp.157–168	h = −6→6
Absorption correction: multi-scan CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −22→22
Tmin = 0.714, Tmax = 1.000	l = −8→7
4613 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.079	H-atom parameters constrained
wR(F^2) = 0.239	w = 1/[σ^2(Fo^2) + (0.1638P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max < 0.001
433 reflections	Δρmax = 0.14 e Å^−3
97 parameters	Δρmin = −0.16 e Å^−3
0 restraints

Special details

Experimental. Data were collected at room temperature and pressure of 1.11 (2) GPa (1110000 kPa) with the crystal obtained by the in-situ high-pressure crystallization technique. Pressure was determined by monitoring the shift of the ruby R1-fluorescence line.

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
N24	0.657 (3)	0.5019 (4)	0.398 (3)	0.035 (2)*
N25	0.563 (3)	0.5581 (3)	0.328 (3)	0.034 (2)*
C26	0.451 (4)	0.5358 (5)	0.223 (3)	0.040 (3)*
C27	0.439 (3)	0.4604 (5)	0.169 (3)	0.046 (3)*
H27	0.3698	0.4494	0.0817	0.055*
C28	0.524 (4)	0.4072 (5)	0.243 (3)	0.044 (3)*
H28	0.5133	0.3582	0.2117	0.053*
C29	0.635 (6)	0.4277 (4)	0.372 (5)	0.039 (3)*
N21	0.751 (3)	0.3902 (4)	0.455 (2)	0.048 (3)*
N22	0.843 (3)	0.4399 (4)	0.543 (3)	0.049 (3)*
C23	0.785 (4)	0.5064 (5)	0.509 (3)	0.039 (3)*
H23	0.8260	0.5500	0.5539	0.047*
N210	0.349 (3)	0.5859 (4)	0.141 (2)	0.044 (2)*
N211	0.367 (3)	0.6512 (4)	0.182 (3)	0.048 (3)*
N212	0.369 (4)	0.7114 (5)	0.206 (3)	0.059 (3)*
N4	0.785 (3)	0.7216 (3)	0.636 (3)	0.037 (2)*
N5	0.880 (3)	0.6670 (3)	0.711 (2)	0.036 (2)*
C6	0.990 (4)	0.6921 (5)	0.812 (3)	0.041 (3)*
C7	1.026 (4)	0.7687 (4)	0.848 (3)	0.051 (3)*
H7	1.1102	0.7816	0.9238	0.062*
C8	0.935 (4)	0.8208 (5)	0.769 (3)	0.048 (3)*
H8	0.9559	0.8708	0.7867	0.058*
C9	0.806 (3)	0.7976 (4)	0.659 (3)	0.035 (3)*
N1	0.708 (3)	0.8321 (4)	0.555 (3)	0.047 (3)*
N2	0.613 (4)	0.7797 (4)	0.473 (3)	0.045 (3)*
C3	0.667 (4)	0.7149 (4)	0.522 (3)	0.039 (3)*
H3	0.6268	0.6701	0.4815	0.046*
N10	1.088 (3)	0.6429 (4)	0.905 (3)	0.045 (2)*
N11	1.073 (5)	0.5759 (4)	0.864 (4)	0.048 (3)*
N12	1.065 (4)	0.5144 (5)	0.849 (3)	0.057 (3)*

Geometric parameters (Å, º)

N24—N25	1.379 (9)	N4—N5	1.376 (9)
N24—C29	1.371 (11)	N4—C9	1.399 (10)
N24—C23	1.348 (10)	N4—C3	1.328 (12)
N25—C26	1.295 (10)	N5—C6	1.281 (11)
C26—C27	1.446 (17)	C6—C7	1.446 (13)
C26—N210	1.377 (12)	C6—N10	1.401 (11)
C27—C28	1.318 (11)	C7—C8	1.350 (12)
C28—C29	1.432 (13)	C8—C9	1.410 (11)
C29—N21	1.313 (13)	C9—N1	1.315 (11)
N21—N22	1.361 (10)	N1—N2	1.379 (11)
N22—C23	1.313 (13)	N2—C3	1.308 (10)
N210—N211	1.242 (11)	N10—N11	1.268 (13)
N211—N212	1.110 (10)	N11—N12	1.122 (10)
C29—N24—N25	126.0 (7)	N5—N4—C9	125.5 (7)
C23—N24—N25	128.8 (7)	C3—N4—N5	128.6 (7)
C23—N24—C29	105.2 (6)	C3—N4—C9	105.7 (6)
C26—N25—N24	114.0 (7)	C6—N5—N4	113.2 (7)
N25—C26—C27	123.7 (10)	N5—C6—C7	127.3 (8)
N25—C26—N210	120.6 (8)	N5—C6—N10	119.7 (7)
N210—C26—C27	115.2 (8)	N10—C6—C7	112.9 (7)
C28—C27—C26	120.6 (10)	C8—C7—C6	117.8 (9)
C27—C28—C29	117.4 (9)	C7—C8—C9	118.3 (8)
N24—C29—C28	116.9 (8)	N4—C9—C8	117.7 (7)
N21—C29—N24	109.7 (8)	N1—C9—N4	107.8 (7)
N21—C29—C28	131.5 (16)	N1—C9—C8	133.9 (9)
C29—N21—N22	107.0 (7)	C9—N1—N2	108.0 (7)
C23—N22—N21	108.4 (7)	C3—N2—N1	107.2 (7)
N22—C23—N24	109.6 (7)	N2—C3—N4	111.0 (7)
N211—N210—C26	114.9 (8)	N11—N10—C6	113.9 (8)
N212—N211—N210	171.6 (9)	N12—N11—N10	170 (3)

6-azido-1,2,4-triazolo[4,3-b]pyridazine (C5H3N7at1.40GPa)

Crystal data

C5H3N7	F(000) = 656
Mr = 161.14	Dx = 1.749 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.7755 (16) Å	Cell parameters from 475 reflections
b = 18.017 (3) Å	θ = 4.3–20.6°
c = 8.75 (3) Å	µ = 0.13 mm^−1
β = 93.53 (9)°	T = 296 K
V = 1224 (4) Å^3	Plate, colorless
Z = 8	0.35 × 0.28 × 0.17 mm

Data collection

KM-4 CCD diffractometer	526 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	274 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.182
Detector resolution: 16.2413 pixels mm^-1	θmax = 27.0°, θmin = 4.3°
HP ω scans – for more details see: A. Budzianowski, A. Katrusiak in High–Pressure Crystallography (Eds.: A. Katrusiak, P. F. McMillan), Dordrecht: Kluwer Acad. Publ., 2004 pp.157–168	h = −9→9
Absorption correction: multi-scan CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −22→22
Tmin = 0.745, Tmax = 1.000	l = −2→2
4881 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.078	H-atom parameters constrained
wR(F^2) = 0.206	w = 1/[σ^2(Fo^2) + (0.0844P)^2 + 0.2618P] where P = (Fo^2 + 2Fc^2)/3
S = 1.12	(Δ/σ)max < 0.001
526 reflections	Δρmax = 0.13 e Å^−3
97 parameters	Δρmin = −0.17 e Å^−3
0 restraints

Special details

Experimental. Data were collected at room temperature and pressure of 1.40 (2) GPa (1400000 kPa) with the crystal obtained by the in-situ high-pressure crystallization technique. Pressure was determined by monitoring the shift of the ruby R1-fluorescence line.

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
N24	0.6603 (11)	0.5015 (4)	0.396 (3)	0.037 (2)*
N25	0.5641 (11)	0.5586 (4)	0.327 (3)	0.041 (2)*
C26	0.4549 (16)	0.5352 (5)	0.215 (5)	0.045 (3)*
C27	0.4338 (16)	0.4612 (5)	0.168 (4)	0.053 (3)*
H27	0.3539	0.4491	0.0890	0.064*
C28	0.5288 (15)	0.4079 (5)	0.239 (5)	0.051 (3)*
H28	0.5185	0.3588	0.2066	0.061*
C29	0.6458 (14)	0.4275 (5)	0.364 (4)	0.043 (3)*
N21	0.7563 (12)	0.3891 (4)	0.454 (4)	0.048 (3)*
N22	0.8395 (12)	0.4404 (4)	0.558 (4)	0.053 (3)*
C23	0.7848 (15)	0.5066 (5)	0.506 (4)	0.046 (3)*
H23	0.8294	0.5514	0.5428	0.055*
N210	0.3459 (13)	0.5870 (4)	0.140 (4)	0.046 (2)*
N211	0.3605 (11)	0.6523 (5)	0.184 (3)	0.052 (3)*
N212	0.3602 (11)	0.7131 (5)	0.209 (3)	0.061 (3)*
N4	0.7858 (10)	0.7216 (4)	0.638 (3)	0.040 (2)*
N5	0.8726 (12)	0.6666 (4)	0.722 (4)	0.047 (3)*
C6	0.9905 (14)	0.6920 (5)	0.813 (5)	0.043 (3)*
C7	1.0233 (13)	0.7692 (5)	0.847 (4)	0.054 (3)*
H7	1.1081	0.7823	0.9220	0.064*
C8	0.9337 (15)	0.8206 (5)	0.773 (5)	0.047 (3)*
H8	0.9492	0.8705	0.7974	0.056*
C9	0.8108 (15)	0.7978 (5)	0.654 (4)	0.042 (3)*
N1	0.7068 (12)	0.8324 (4)	0.549 (3)	0.055 (3)*
N2	0.6141 (10)	0.7790 (4)	0.474 (3)	0.050 (3)*
C3	0.6621 (14)	0.7136 (5)	0.523 (4)	0.046 (3)*
H3	0.6184	0.6687	0.4858	0.055*
N10	1.0923 (11)	0.6422 (4)	0.898 (3)	0.051 (3)*
N11	1.0709 (12)	0.5754 (4)	0.863 (4)	0.053 (3)*
N12	1.0659 (12)	0.5136 (5)	0.850 (4)	0.071 (3)*

Geometric parameters (Å, º)

N24—N25	1.389 (15)	N4—N5	1.39 (2)
N24—C29	1.366 (13)	N4—C9	1.392 (11)
N24—C23	1.33 (2)	N4—C3	1.35 (3)
N25—C26	1.33 (3)	N5—C6	1.26 (2)
C26—C27	1.400 (18)	C6—C7	1.441 (15)
C26—N210	1.40 (2)	C6—N10	1.38 (2)
C27—C28	1.34 (2)	C7—C8	1.31 (2)
C28—C29	1.43 (4)	C8—C9	1.43 (3)
C29—N21	1.32 (2)	C9—N1	1.34 (3)
N21—N22	1.42 (2)	N1—N2	1.348 (17)
N22—C23	1.336 (16)	N2—C3	1.301 (13)
N210—N211	1.240 (16)	N10—N11	1.251 (13)
N211—N212	1.118 (12)	N11—N12	1.120 (11)
C29—N24—N25	126.9 (16)	N5—N4—C9	126.3 (15)
C23—N24—N25	128.0 (10)	C3—N4—N5	128.2 (10)
C23—N24—C29	105.1 (12)	C3—N4—C9	105.5 (12)
C26—N25—N24	112.9 (10)	C6—N5—N4	112.7 (10)
N25—C26—C27	125.1 (16)	N5—C6—C7	126.4 (13)
N25—C26—N210	118.4 (12)	N5—C6—N10	118.2 (9)
N210—C26—C27	116 (2)	N10—C6—C7	115.2 (17)
C28—C27—C26	120 (2)	C8—C7—C6	119.9 (19)
C27—C28—C29	119.0 (15)	C7—C8—C9	118.0 (12)
N24—C29—C28	116.0 (14)	N4—C9—C8	116.0 (14)
N21—C29—N24	110.4 (17)	N1—C9—N4	108.4 (15)
N21—C29—C28	133.4 (12)	N1—C9—C8	135.6 (10)
C29—N21—N22	107.0 (10)	C9—N1—N2	106.6 (11)
C23—N22—N21	103.8 (17)	C3—N2—N1	110.5 (13)
N24—C23—N22	112.9 (12)	N2—C3—N4	109.0 (10)
N211—N210—C26	116.5 (18)	N11—N10—C6	115.3 (17)
N212—N211—N210	172 (2)	N12—N11—N10	170 (3)

3-methyl-6-azido-1,2,4-triazolo[4,3-b]pyridazine (C6H5N7.H2Oat296K)

Crystal data

C6H5N7·0.3(O)	Dx = 1.451 Mg m^−3
Mr = 179.97	Cu Kα radiation, λ = 1.54184 Å
Tetragonal, I41/a	Cell parameters from 5855 reflections
a = 28.1674 (5) Å	θ = 3.1–76.1°
c = 4.15209 (11) Å	µ = 0.90 mm^−1
V = 3294.29 (14) Å^3	T = 296 K
Z = 16	Plate, colorless
F(000) = 1478	0.39 × 0.29 × 0.12 mm

Data collection

SuperNova, Single source at offset, Atlas diffractometer	1725 independent reflections
Radiation source: sealed X-ray tube, SuperNova (Cu) X-ray Source	1533 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.019
Detector resolution: 10.5357 pixels mm^-1	θmax = 76.6°, θmin = 6.3°
ω scans	h = −34→35
Absorption correction: multi-scan CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −35→31
Tmin = 0.915, Tmax = 1.000	l = −3→5
11092 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.037	H-atom parameters constrained
wR(F^2) = 0.108	w = 1/[σ^2(Fo^2) + (0.060P)^2 + 0.5562P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
1725 reflections	Δρmax = 0.10 e Å^−3
128 parameters	Δρmin = −0.14 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	Occ. (<1)
N5	0.57725 (3)	0.61830 (3)	0.8460 (2)	0.0545 (3)
N4	0.58664 (3)	0.58068 (3)	1.0428 (2)	0.0549 (3)
N10	0.60929 (5)	0.67919 (4)	0.5377 (3)	0.0783 (4)
N11	0.56701 (5)	0.68658 (4)	0.4586 (3)	0.0739 (3)
N2	0.57674 (5)	0.51959 (4)	1.3535 (3)	0.0784 (4)
C3	0.55422 (5)	0.55222 (4)	1.1877 (3)	0.0607 (3)
N12	0.53108 (7)	0.69623 (6)	0.3698 (4)	0.0985 (5)
N1	0.62499 (5)	0.52655 (4)	1.3186 (4)	0.0871 (4)
C6	0.61525 (4)	0.63965 (4)	0.7458 (3)	0.0614 (3)
C8	0.67056 (5)	0.58905 (6)	1.0123 (5)	0.0841 (5)
H8	0.701250	0.579520	1.063672	0.101*
C9	0.63066 (5)	0.56386 (5)	1.1299 (4)	0.0695 (4)
C13	0.50257 (5)	0.55931 (5)	1.1626 (4)	0.0732 (4)
H13A	0.493146	0.557381	0.940790	0.110*
H13B	0.494397	0.589996	1.246614	0.110*
H13C	0.486473	0.535185	1.284052	0.110*
C7	0.66285 (5)	0.62712 (6)	0.8245 (4)	0.0781 (4)
H7	0.688164	0.644982	0.747108	0.094*
O1	0.7337 (12)	0.4877 (15)	0.324 (16)	0.209 (9)	0.3

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N5	0.0587 (5)	0.0457 (4)	0.0591 (5)	−0.0038 (4)	0.0040 (4)	0.0011 (4)
N4	0.0581 (5)	0.0469 (5)	0.0595 (5)	−0.0012 (4)	−0.0021 (4)	−0.0002 (4)
N10	0.0855 (8)	0.0645 (6)	0.0850 (8)	−0.0153 (6)	0.0212 (6)	0.0093 (6)
N11	0.0935 (9)	0.0561 (6)	0.0720 (7)	−0.0008 (6)	0.0161 (6)	0.0080 (5)
N2	0.0956 (9)	0.0575 (6)	0.0820 (8)	−0.0043 (5)	−0.0145 (7)	0.0132 (5)
C3	0.0723 (7)	0.0481 (5)	0.0618 (7)	−0.0069 (5)	−0.0027 (5)	0.0039 (5)
N12	0.1095 (12)	0.0862 (9)	0.0999 (11)	0.0196 (8)	0.0007 (9)	0.0187 (8)
N1	0.0930 (9)	0.0659 (7)	0.1023 (10)	0.0098 (6)	−0.0274 (8)	0.0070 (6)
C6	0.0633 (7)	0.0543 (6)	0.0667 (7)	−0.0091 (5)	0.0117 (5)	−0.0059 (5)
C8	0.0565 (7)	0.0839 (10)	0.1120 (12)	0.0067 (6)	−0.0088 (8)	−0.0175 (9)
C9	0.0643 (7)	0.0603 (7)	0.0839 (9)	0.0066 (5)	−0.0128 (6)	−0.0080 (6)
C13	0.0703 (8)	0.0667 (7)	0.0826 (9)	−0.0122 (6)	0.0069 (7)	0.0130 (6)
C7	0.0588 (7)	0.0783 (9)	0.0973 (11)	−0.0123 (6)	0.0124 (7)	−0.0143 (8)
O1	0.157 (13)	0.170 (12)	0.30 (3)	−0.026 (6)	−0.061 (17)	0.045 (12)

Geometric parameters (Å, º)

N5—N4	1.3642 (13)	C6—C7	1.424 (2)
N5—C6	1.2962 (15)	C8—H8	0.9300
N4—C3	1.3561 (16)	C8—C9	1.416 (2)
N4—C9	1.3757 (16)	C8—C7	1.343 (2)
N10—N11	1.2530 (19)	C13—H13A	0.9600
N10—C6	1.4195 (18)	C13—H13B	0.9600
N11—N12	1.111 (2)	C13—H13C	0.9600
N2—C3	1.3118 (18)	C7—H7	0.9300
N2—N1	1.381 (2)	O1—O1^i	1.319 (8)
C3—C13	1.472 (2)	O1—O1^ii	1.319 (8)
N1—C9	1.320 (2)
C6—N5—N4	113.10 (10)	C7—C8—H8	120.9
N5—N4—C9	126.86 (11)	C7—C8—C9	118.15 (13)
C3—N4—N5	126.47 (10)	N4—C9—C8	116.87 (13)
C3—N4—C9	106.67 (11)	N1—C9—N4	108.72 (13)
N11—N10—C6	113.73 (11)	N1—C9—C8	134.39 (14)
N12—N11—N10	173.56 (15)	C3—C13—H13A	109.5
C3—N2—N1	108.74 (12)	C3—C13—H13B	109.5
N4—C3—C13	123.64 (11)	C3—C13—H13C	109.5
N2—C3—N4	108.74 (12)	H13A—C13—H13B	109.5
N2—C3—C13	127.59 (12)	H13A—C13—H13C	109.5
C9—N1—N2	107.13 (12)	H13B—C13—H13C	109.5
N5—C6—N10	117.49 (12)	C6—C7—H7	120.6
N5—C6—C7	126.07 (13)	C8—C7—C6	118.89 (13)
N10—C6—C7	116.44 (12)	C8—C7—H7	120.6
C9—C8—H8	120.9	O1^i—O1—O1^ii	128.3 (6)
N5—N4—C3—N2	179.05 (11)	C3—N4—C9—N1	0.32 (15)
N5—N4—C3—C13	−2.6 (2)	C3—N4—C9—C8	−178.43 (13)
N5—N4—C9—N1	−178.99 (11)	C3—N2—N1—C9	0.09 (18)
N5—N4—C9—C8	2.3 (2)	N1—N2—C3—N4	0.11 (16)
N5—C6—C7—C8	2.0 (2)	N1—N2—C3—C13	−178.14 (14)
N4—N5—C6—N10	179.64 (10)	C6—N5—N4—C3	178.87 (11)
N4—N5—C6—C7	−0.22 (18)	C6—N5—N4—C9	−1.96 (17)
N10—C6—C7—C8	−177.90 (14)	C9—N4—C3—N2	−0.26 (15)
N11—N10—C6—N5	−4.60 (19)	C9—N4—C3—C13	178.08 (13)
N11—N10—C6—C7	175.28 (13)	C9—C8—C7—C6	−1.6 (2)
N2—N1—C9—N4	−0.25 (17)	C7—C8—C9—N4	−0.3 (2)
N2—N1—C9—C8	178.18 (17)	C7—C8—C9—N1	−178.65 (16)

Symmetry codes: (i) −y+5/4, x−1/4, z−1/4; (ii) y+1/4, −x+5/4, z+1/4.

3-methyl-6-azido-1,2,4-triazolo[4,3-b]pyridazine (C6H5N7.H2Oat250K)

Crystal data

C6H5N7·0.4(O)	Dx = 1.475 Mg m^−3
Mr = 181.57	Cu Kα radiation, λ = 1.54184 Å
Tetragonal, I41/a	Cell parameters from 2623 reflections
a = 28.1659 (3) Å	θ = 3.1–76.1°
c = 4.12335 (8) Å	µ = 0.92 mm^−1
V = 3271.13 (10) Å^3	T = 250 K
Z = 16	Plate, colorless
F(000) = 1491	0.39 × 0.29 × 0.12 mm

Data collection

SuperNova, Single source at offset/far, Atlas diffractometer	1693 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source	1533 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.011
Detector resolution: 10.5357 pixels mm^-1	θmax = 76.4°, θmin = 3.1°
ω scans	h = −33→33
Absorption correction: multi-scan CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −29→35
Tmin = 0.933, Tmax = 1.000	l = −2→5
3756 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.035	w = 1/[σ^2(Fo^2) + (0.0572P)^2 + 0.7353P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.101	(Δ/σ)max = 0.001
S = 1.04	Δρmax = 0.14 e Å^−3
1693 reflections	Δρmin = −0.16 e Å^−3
129 parameters	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.00058 (11)
Primary atom site location: structure-invariant direct methods

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
N5	0.57707 (3)	0.61845 (3)	0.8473 (2)	0.0445 (2)
N4	0.58651 (3)	0.58075 (3)	1.0452 (2)	0.0452 (2)
N10	0.60936 (4)	0.67964 (4)	0.5401 (3)	0.0639 (3)
N11	0.56712 (5)	0.68691 (4)	0.4595 (3)	0.0601 (3)
N2	0.57651 (5)	0.51952 (4)	1.3563 (3)	0.0659 (3)
C3	0.55399 (4)	0.55206 (4)	1.1885 (3)	0.0503 (3)
N12	0.53103 (6)	0.69645 (5)	0.3690 (4)	0.0805 (4)
N1	0.62492 (5)	0.52673 (4)	1.3238 (4)	0.0736 (4)
C6	0.61520 (4)	0.63998 (4)	0.7490 (3)	0.0500 (3)
C8	0.67055 (5)	0.58950 (5)	1.0197 (4)	0.0700 (4)
H8	0.701212	0.580131	1.073665	0.084*
C9	0.63051 (4)	0.56408 (4)	1.1347 (3)	0.0579 (3)
C13	0.50224 (5)	0.55895 (5)	1.1600 (4)	0.0607 (3)
H13A	0.493136	0.557021	0.935987	0.091*
H13B	0.493822	0.589586	1.244280	0.091*
H13C	0.486087	0.534730	1.281015	0.091*
C7	0.66286 (5)	0.62758 (5)	0.8301 (4)	0.0642 (4)
H7	0.688181	0.645526	0.753087	0.077*
O1	0.7283 (2)	0.4982 (9)	0.420 (7)	0.201 (5)	0.4

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N5	0.0488 (5)	0.0388 (4)	0.0459 (5)	−0.0029 (3)	0.0026 (4)	0.0011 (3)
N4	0.0491 (5)	0.0386 (4)	0.0477 (5)	−0.0004 (3)	−0.0031 (4)	−0.0005 (3)
N10	0.0683 (7)	0.0537 (6)	0.0697 (7)	−0.0122 (5)	0.0167 (5)	0.0077 (5)
N11	0.0770 (8)	0.0460 (5)	0.0575 (6)	−0.0002 (5)	0.0131 (5)	0.0067 (4)
N2	0.0844 (8)	0.0478 (5)	0.0657 (7)	−0.0037 (5)	−0.0139 (6)	0.0103 (5)
C3	0.0627 (7)	0.0403 (5)	0.0480 (6)	−0.0064 (4)	−0.0022 (5)	0.0028 (4)
N12	0.0917 (10)	0.0704 (8)	0.0794 (9)	0.0166 (7)	0.0010 (7)	0.0155 (6)
N1	0.0816 (8)	0.0548 (6)	0.0843 (8)	0.0091 (5)	−0.0260 (7)	0.0054 (6)
C6	0.0522 (6)	0.0446 (5)	0.0533 (6)	−0.0069 (4)	0.0090 (5)	−0.0061 (5)
C8	0.0481 (6)	0.0711 (8)	0.0908 (10)	0.0061 (6)	−0.0095 (7)	−0.0162 (8)
C9	0.0554 (7)	0.0504 (6)	0.0679 (8)	0.0066 (5)	−0.0131 (6)	−0.0079 (5)
C13	0.0604 (7)	0.0559 (7)	0.0660 (8)	−0.0102 (5)	0.0062 (6)	0.0103 (6)
C7	0.0475 (6)	0.0657 (8)	0.0793 (9)	−0.0093 (5)	0.0095 (6)	−0.0139 (7)
O1	0.113 (4)	0.178 (7)	0.311 (19)	0.004 (6)	−0.007 (9)	0.046 (8)

Geometric parameters (Å, º)

N5—N4	1.3651 (12)	C6—C7	1.4269 (18)
N5—C6	1.2982 (14)	C8—H8	0.9300
N4—C3	1.3570 (15)	C8—C9	1.418 (2)
N4—C9	1.3757 (15)	C8—C7	1.345 (2)
N10—N11	1.2521 (17)	C13—H13A	0.9600
N10—C6	1.4201 (16)	C13—H13B	0.9600
N11—N12	1.1157 (18)	C13—H13C	0.9600
N2—C3	1.3120 (17)	C7—H7	0.9300
N2—N1	1.3852 (19)	O1—O1^i	1.347 (5)
C3—C13	1.4750 (18)	O1—O1^ii	1.347 (5)
N1—C9	1.3188 (19)
C6—N5—N4	112.88 (9)	C7—C8—H8	121.0
N5—N4—C9	126.96 (10)	C7—C8—C9	117.98 (12)
C3—N4—N5	126.30 (9)	N4—C9—C8	117.03 (12)
C3—N4—C9	106.74 (10)	N1—C9—N4	108.88 (12)
N11—N10—C6	113.56 (10)	N1—C9—C8	134.07 (13)
N12—N11—N10	173.65 (14)	C3—C13—H13A	109.5
C3—N2—N1	108.81 (11)	C3—C13—H13B	109.5
N4—C3—C13	123.64 (10)	C3—C13—H13C	109.5
N2—C3—N4	108.62 (11)	H13A—C13—H13B	109.5
N2—C3—C13	127.72 (11)	H13A—C13—H13C	109.5
C9—N1—N2	106.95 (11)	H13B—C13—H13C	109.5
N5—C6—N10	117.46 (11)	C6—C7—H7	120.6
N5—C6—C7	126.21 (12)	C8—C7—C6	118.88 (12)
N10—C6—C7	116.33 (11)	C8—C7—H7	120.6
C9—C8—H8	121.0	O1^i—O1—O1^ii	125.8 (3)
N5—N4—C3—N2	179.14 (10)	C3—N4—C9—N1	0.19 (14)
N5—N4—C3—C13	−2.55 (18)	C3—N4—C9—C8	−178.38 (12)
N5—N4—C9—N1	−179.06 (11)	C3—N2—N1—C9	0.11 (16)
N5—N4—C9—C8	2.37 (18)	N1—N2—C3—N4	0.01 (15)
N5—C6—C7—C8	1.7 (2)	N1—N2—C3—C13	−178.21 (13)
N4—N5—C6—N10	179.69 (9)	C6—N5—N4—C3	178.93 (10)
N4—N5—C6—C7	−0.15 (17)	C6—N5—N4—C9	−1.95 (15)
N10—C6—C7—C8	−178.15 (13)	C9—N4—C3—N2	−0.12 (13)
N11—N10—C6—N5	−4.47 (17)	C9—N4—C3—C13	178.19 (12)
N11—N10—C6—C7	175.39 (11)	C9—C8—C7—C6	−1.2 (2)
N2—N1—C9—N4	−0.18 (15)	C7—C8—C9—N4	−0.6 (2)
N2—N1—C9—C8	178.04 (15)	C7—C8—C9—N1	−178.70 (15)

Symmetry codes: (i) −y+5/4, x−1/4, z−1/4; (ii) y+1/4, −x+5/4, z+1/4.

3-methyl-6-azido-1,2,4-triazolo[4,3-b]pyridazine (C6H5N7.H2Oat200K)

Crystal data

C6H5N7·0.4(O)	Dx = 1.489 Mg m^−3
Mr = 181.57	Cu Kα radiation, λ = 1.54184 Å
Tetragonal, I41/a	Cell parameters from 2678 reflections
a = 28.1314 (4) Å	θ = 2.2–76.0°
c = 4.09378 (10) Å	µ = 0.93 mm^−1
V = 3239.72 (12) Å^3	T = 200 K
Z = 16	Plate, colorless
F(000) = 1491	0.39 × 0.29 × 0.12 mm

Data collection

SuperNova, Single source at offset/far, Atlas diffractometer	1677 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source	1534 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.010
Detector resolution: 10.5357 pixels mm^-1	θmax = 76.2°, θmin = 3.1°
ω scans	h = −35→29
Absorption correction: multi-scan CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −33→33
Tmin = 0.909, Tmax = 1.000	l = −2→5
3689 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.035	H-atom parameters constrained
wR(F^2) = 0.101	w = 1/[σ^2(Fo^2) + (0.0578P)^2 + 1.0453P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
1677 reflections	Δρmax = 0.13 e Å^−3
128 parameters	Δρmin = −0.15 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	Occ. (<1)
N5	0.57699 (3)	0.61861 (3)	0.8484 (2)	0.0375 (2)
N4	0.58650 (3)	0.58080 (3)	1.0469 (2)	0.0381 (2)
N10	0.60946 (4)	0.68017 (4)	0.5426 (3)	0.0532 (3)
N11	0.56711 (4)	0.68727 (4)	0.4604 (3)	0.0499 (3)
N2	0.57657 (5)	0.51935 (4)	1.3587 (3)	0.0546 (3)
C3	0.55394 (4)	0.55188 (4)	1.1894 (3)	0.0423 (3)
N12	0.53092 (5)	0.69662 (5)	0.3684 (3)	0.0659 (4)
N1	0.62503 (5)	0.52681 (4)	1.3285 (3)	0.0615 (3)
C6	0.61520 (4)	0.64040 (4)	0.7514 (3)	0.0420 (3)
C8	0.67070 (5)	0.59002 (5)	1.0263 (4)	0.0583 (4)
H8	0.701375	0.580805	1.082536	0.070*
C9	0.63055 (4)	0.56431 (4)	1.1391 (3)	0.0484 (3)
C13	0.50207 (5)	0.55860 (5)	1.1580 (3)	0.0500 (3)
H13A	0.493245	0.556935	0.931737	0.075*
H13B	0.493405	0.589126	1.244321	0.075*
H13C	0.485848	0.534124	1.277410	0.075*
C7	0.66295 (5)	0.62818 (5)	0.8353 (4)	0.0535 (3)
H7	0.688279	0.646303	0.759237	0.064*
O1	0.72780 (18)	0.4990 (6)	0.426 (5)	0.180 (4)	0.4

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N5	0.0415 (5)	0.0327 (4)	0.0384 (5)	−0.0023 (3)	0.0018 (4)	0.0007 (4)
N4	0.0419 (5)	0.0327 (4)	0.0398 (5)	−0.0002 (3)	−0.0025 (4)	−0.0006 (3)
N10	0.0552 (6)	0.0458 (6)	0.0584 (7)	−0.0098 (5)	0.0129 (5)	0.0063 (5)
N11	0.0635 (7)	0.0377 (5)	0.0485 (6)	−0.0010 (5)	0.0109 (5)	0.0056 (4)
N2	0.0699 (7)	0.0396 (5)	0.0542 (6)	−0.0034 (5)	−0.0115 (5)	0.0081 (5)
C3	0.0528 (6)	0.0344 (5)	0.0397 (6)	−0.0052 (4)	−0.0016 (5)	0.0022 (4)
N12	0.0745 (9)	0.0583 (7)	0.0649 (8)	0.0126 (6)	0.0012 (7)	0.0129 (6)
N1	0.0676 (7)	0.0462 (6)	0.0708 (8)	0.0076 (5)	−0.0222 (6)	0.0038 (5)
C6	0.0442 (6)	0.0374 (5)	0.0442 (6)	−0.0053 (4)	0.0073 (5)	−0.0051 (5)
C8	0.0410 (6)	0.0585 (8)	0.0753 (9)	0.0055 (5)	−0.0093 (6)	−0.0135 (7)
C9	0.0464 (6)	0.0421 (6)	0.0568 (7)	0.0054 (5)	−0.0112 (5)	−0.0072 (5)
C13	0.0502 (7)	0.0456 (6)	0.0543 (7)	−0.0083 (5)	0.0049 (6)	0.0078 (5)
C7	0.0397 (6)	0.0546 (7)	0.0663 (8)	−0.0072 (5)	0.0070 (6)	−0.0123 (6)
O1	0.097 (3)	0.145 (5)	0.297 (15)	0.003 (5)	0.002 (7)	0.023 (6)

Geometric parameters (Å, º)

N5—N4	1.3651 (13)	C6—C7	1.4286 (18)
N5—C6	1.2995 (15)	C8—H8	0.9300
N4—C3	1.3569 (15)	C8—C9	1.418 (2)
N4—C9	1.3759 (15)	C8—C7	1.346 (2)
N10—N11	1.2541 (17)	C13—H13A	0.9600
N10—C6	1.4171 (16)	C13—H13B	0.9600
N11—N12	1.1168 (18)	C13—H13C	0.9600
N2—C3	1.3124 (16)	C7—H7	0.9300
N2—N1	1.3849 (18)	O1—O1^i	1.352 (5)
C3—C13	1.4771 (18)	O1—O1^ii	1.352 (5)
N1—C9	1.3184 (18)
C6—N5—N4	112.79 (9)	C7—C8—H8	121.1
N5—N4—C9	127.06 (10)	C7—C8—C9	117.83 (12)
C3—N4—N5	126.23 (10)	N4—C9—C8	117.12 (12)
C3—N4—C9	106.71 (10)	N1—C9—N4	108.97 (12)
N11—N10—C6	113.32 (10)	N1—C9—C8	133.88 (12)
N12—N11—N10	173.71 (13)	C3—C13—H13A	109.5
C3—N2—N1	108.94 (11)	C3—C13—H13B	109.5
N4—C3—C13	123.53 (10)	C3—C13—H13C	109.5
N2—C3—N4	108.53 (11)	H13A—C13—H13B	109.5
N2—C3—C13	127.91 (11)	H13A—C13—H13C	109.5
C9—N1—N2	106.83 (11)	H13B—C13—H13C	109.5
N5—C6—N10	117.55 (11)	C6—C7—H7	120.5
N5—C6—C7	126.20 (11)	C8—C7—C6	118.96 (12)
N10—C6—C7	116.25 (11)	C8—C7—H7	120.5
C9—C8—H8	121.1	O1^i—O1—O1^ii	124.9 (3)
N5—N4—C3—N2	179.27 (10)	C3—N4—C9—N1	0.27 (14)
N5—N4—C3—C13	−2.35 (18)	C3—N4—C9—C8	−178.21 (11)
N5—N4—C9—N1	−179.21 (11)	C3—N2—N1—C9	0.08 (16)
N5—N4—C9—C8	2.31 (18)	N1—N2—C3—N4	0.09 (15)
N5—C6—C7—C8	1.7 (2)	N1—N2—C3—C13	−178.20 (12)
N4—N5—C6—N10	179.75 (10)	C6—N5—N4—C3	178.87 (11)
N4—N5—C6—C7	−0.34 (17)	C6—N5—N4—C9	−1.74 (16)
N10—C6—C7—C8	−178.37 (12)	C9—N4—C3—N2	−0.22 (13)
N11—N10—C6—N5	−4.49 (17)	C9—N4—C3—C13	178.16 (11)
N11—N10—C6—C7	175.58 (11)	C9—C8—C7—C6	−1.1 (2)
N2—N1—C9—N4	−0.22 (15)	C7—C8—C9—N4	−0.72 (19)
N2—N1—C9—C8	177.91 (15)	C7—C8—C9—N1	−178.72 (15)

Symmetry codes: (i) y+1/4, −x+5/4, z+1/4; (ii) −y+5/4, x−1/4, z−1/4.

3-methyl-6-azido-1,2,4-triazolo[4,3-b]pyridazine (C6H5N7.H2Oat150K)

Crystal data

C6H5N7·0.4(O)	Dx = 1.501 Mg m^−3
Mr = 181.57	Cu Kα radiation, λ = 1.54184 Å
Tetragonal, I41/a	Cell parameters from 2415 reflections
a = 28.1081 (4) Å	θ = 3.1–76.0°
c = 4.06918 (11) Å	µ = 0.93 mm^−1
V = 3214.91 (13) Å^3	T = 150 K
Z = 16	Plate, colorless
F(000) = 1491	0.39 × 0.29 × 0.12 mm

Data collection

SuperNova, Single source at offset/far, Atlas diffractometer	1661 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source	1542 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.012
Detector resolution: 10.5357 pixels mm^-1	θmax = 76.2°, θmin = 3.1°
ω scans	h = −33→33
Absorption correction: multi-scan CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −35→29
Tmin = 0.895, Tmax = 1.000	l = −2→5
3636 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.035	H-atom parameters constrained
wR(F^2) = 0.097	w = 1/[σ^2(Fo^2) + (0.0528P)^2 + 1.5784P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
1661 reflections	Δρmax = 0.16 e Å^−3
128 parameters	Δρmin = −0.15 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	Occ. (<1)
N5	0.57692 (3)	0.61876 (3)	0.8490 (2)	0.0314 (2)
N4	0.58651 (3)	0.58087 (3)	1.0487 (2)	0.0319 (2)
N10	0.60950 (4)	0.68064 (4)	0.5440 (3)	0.0432 (3)
N11	0.56706 (4)	0.68757 (4)	0.4606 (3)	0.0406 (3)
N2	0.57661 (4)	0.51919 (4)	1.3610 (3)	0.0455 (3)
C3	0.55392 (4)	0.55167 (4)	1.1902 (3)	0.0354 (3)
N12	0.53066 (5)	0.69677 (4)	0.3676 (3)	0.0532 (3)
N1	0.62517 (5)	0.52685 (4)	1.3328 (3)	0.0515 (3)
C6	0.61521 (4)	0.64078 (4)	0.7534 (3)	0.0349 (3)
C8	0.67090 (5)	0.59042 (5)	1.0309 (4)	0.0487 (4)
H8	0.701593	0.581265	1.088176	0.058*
C9	0.63064 (4)	0.56451 (4)	1.1426 (3)	0.0410 (3)
C13	0.50194 (5)	0.55828 (4)	1.1564 (3)	0.0414 (3)
H13A	0.493310	0.556595	0.928468	0.062*
H13B	0.493118	0.588802	1.242996	0.062*
H13C	0.485665	0.533734	1.275882	0.062*
C7	0.66311 (4)	0.62868 (5)	0.8395 (4)	0.0443 (3)
H7	0.688431	0.646980	0.764262	0.053*
O1	0.72773 (16)	0.4988 (4)	0.434 (4)	0.162 (4)	0.4

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N5	0.0346 (5)	0.0273 (4)	0.0324 (5)	−0.0019 (3)	0.0010 (4)	0.0006 (4)
N4	0.0355 (5)	0.0271 (4)	0.0332 (5)	−0.0003 (3)	−0.0022 (4)	−0.0003 (4)
N10	0.0438 (6)	0.0374 (5)	0.0486 (6)	−0.0079 (4)	0.0097 (5)	0.0046 (5)
N11	0.0520 (7)	0.0307 (5)	0.0390 (6)	−0.0014 (4)	0.0088 (5)	0.0044 (4)
N2	0.0586 (7)	0.0327 (5)	0.0452 (6)	−0.0030 (4)	−0.0101 (5)	0.0057 (4)
C3	0.0447 (6)	0.0284 (5)	0.0332 (6)	−0.0046 (4)	−0.0016 (5)	0.0010 (4)
N12	0.0604 (8)	0.0466 (6)	0.0525 (7)	0.0097 (5)	0.0015 (6)	0.0094 (5)
N1	0.0561 (7)	0.0383 (6)	0.0600 (7)	0.0061 (5)	−0.0195 (6)	0.0027 (5)
C6	0.0369 (6)	0.0311 (5)	0.0367 (6)	−0.0041 (4)	0.0052 (5)	−0.0049 (5)
C8	0.0344 (6)	0.0481 (7)	0.0636 (9)	0.0043 (5)	−0.0081 (6)	−0.0120 (6)
C9	0.0396 (6)	0.0349 (6)	0.0486 (7)	0.0045 (5)	−0.0109 (5)	−0.0064 (5)
C13	0.0428 (6)	0.0375 (6)	0.0439 (7)	−0.0070 (5)	0.0043 (5)	0.0062 (5)
C7	0.0332 (6)	0.0442 (7)	0.0556 (8)	−0.0057 (5)	0.0049 (5)	−0.0104 (6)
O1	0.085 (3)	0.121 (4)	0.279 (13)	0.006 (4)	0.001 (7)	0.016 (5)

Geometric parameters (Å, º)

N5—N4	1.3664 (13)	C6—C7	1.4319 (17)
N5—C6	1.3011 (15)	C8—H8	0.9300
N4—C3	1.3581 (15)	C8—C9	1.420 (2)
N4—C9	1.3771 (15)	C8—C7	1.346 (2)
N10—N11	1.2555 (16)	C13—H13A	0.9600
N10—C6	1.4165 (16)	C13—H13B	0.9600
N11—N12	1.1210 (17)	C13—H13C	0.9600
N2—C3	1.3128 (16)	C7—H7	0.9300
N2—N1	1.3866 (18)	O1—O1^i	1.349 (4)
C3—C13	1.4792 (18)	O1—O1^ii	1.349 (4)
N1—C9	1.3202 (18)
C6—N5—N4	112.68 (10)	C7—C8—H8	121.1
N5—N4—C9	127.07 (10)	C7—C8—C9	117.73 (12)
C3—N4—N5	126.18 (10)	N4—C9—C8	117.24 (12)
C3—N4—C9	106.74 (10)	N1—C9—N4	108.99 (12)
N11—N10—C6	113.16 (10)	N1—C9—C8	133.75 (12)
N12—N11—N10	173.84 (13)	C3—C13—H13A	109.5
C3—N2—N1	109.04 (11)	C3—C13—H13B	109.5
N4—C3—C13	123.42 (10)	C3—C13—H13C	109.5
N2—C3—N4	108.49 (11)	H13A—C13—H13B	109.5
N2—C3—C13	128.06 (11)	H13A—C13—H13C	109.5
C9—N1—N2	106.73 (10)	H13B—C13—H13C	109.5
N5—C6—N10	117.53 (11)	C6—C7—H7	120.5
N5—C6—C7	126.27 (11)	C8—C7—C6	118.97 (12)
N10—C6—C7	116.20 (11)	C8—C7—H7	120.5
C9—C8—H8	121.1	O1^i—O1—O1^ii	124.6 (3)
N5—N4—C3—N2	179.26 (10)	C3—N4—C9—N1	0.14 (14)
N5—N4—C3—C13	−2.51 (19)	C3—N4—C9—C8	−178.33 (11)
N5—N4—C9—N1	−179.19 (11)	C3—N2—N1—C9	0.11 (15)
N5—N4—C9—C8	2.34 (18)	N1—N2—C3—N4	−0.02 (15)
N5—C6—C7—C8	1.7 (2)	N1—N2—C3—C13	−178.14 (12)
N4—N5—C6—N10	179.81 (10)	C6—N5—N4—C3	178.94 (11)
N4—N5—C6—C7	−0.24 (17)	C6—N5—N4—C9	−1.86 (16)
N10—C6—C7—C8	−178.32 (12)	C9—N4—C3—N2	−0.07 (14)
N11—N10—C6—N5	−4.36 (16)	C9—N4—C3—C13	178.16 (11)
N11—N10—C6—C7	175.68 (11)	C9—C8—C7—C6	−1.2 (2)
N2—N1—C9—N4	−0.15 (15)	C7—C8—C9—N4	−0.63 (19)
N2—N1—C9—C8	177.97 (15)	C7—C8—C9—N1	−178.63 (15)

Symmetry codes: (i) −y+5/4, x−1/4, z−1/4; (ii) y+1/4, −x+5/4, z+1/4.

3-methyl-6-azido-1,2,4-triazolo[4,3-b]pyridazine (C6H5N7.H2Oat100K)

Crystal data

C6H5N7·0.4(O)	Dx = 1.512 Mg m^−3
Mr = 181.57	Cu Kα radiation, λ = 1.54184 Å
Tetragonal, I41/a	Cell parameters from 2268 reflections
a = 28.0757 (5) Å	θ = 3.1–76.3°
c = 4.04859 (12) Å	µ = 0.94 mm^−1
V = 3191.28 (14) Å^3	T = 100 K
Z = 16	Plate, colorless
F(000) = 1491	0.39 × 0.29 × 0.12 mm

Data collection

SuperNova, Single source at offset, Atlas diffractometer	1644 independent reflections
Radiation source: sealed X-ray tube, SuperNova (Cu) X-ray Source	1545 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.013
Detector resolution: 10.5357 pixels mm^-1	θmax = 76.4°, θmin = 3.2°
ω scans	h = −35→29
Absorption correction: multi-scan CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −33→33
Tmin = 0.926, Tmax = 1.000	l = −2→5
3568 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.035	H-atom parameters constrained
wR(F^2) = 0.098	w = 1/[σ^2(Fo^2) + (0.053P)^2 + 1.9391P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
1644 reflections	Δρmax = 0.20 e Å^−3
128 parameters	Δρmin = −0.18 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	Occ. (<1)
N5	0.57692 (3)	0.61884 (3)	0.8496 (2)	0.0267 (2)
N4	0.58653 (3)	0.58087 (3)	1.0502 (3)	0.0274 (2)
N10	0.60949 (4)	0.68100 (4)	0.5448 (3)	0.0354 (3)
N11	0.56694 (4)	0.68777 (4)	0.4605 (3)	0.0330 (3)
N2	0.57660 (4)	0.51904 (4)	1.3632 (3)	0.0383 (3)
C3	0.55390 (5)	0.55156 (4)	1.1909 (3)	0.0302 (3)
N12	0.53040 (5)	0.69687 (4)	0.3670 (3)	0.0421 (3)
N1	0.62529 (5)	0.52685 (4)	1.3358 (3)	0.0438 (3)
C6	0.61520 (4)	0.64105 (4)	0.7546 (3)	0.0293 (3)
C8	0.67106 (5)	0.59068 (5)	1.0346 (4)	0.0414 (3)
H8	0.701782	0.581562	1.092672	0.050*
C9	0.63073 (5)	0.56466 (4)	1.1454 (3)	0.0349 (3)
C13	0.50179 (5)	0.55802 (4)	1.1552 (3)	0.0343 (3)
H13A	0.493372	0.556797	0.925509	0.051*
H13B	0.492724	0.588337	1.245006	0.051*
H13C	0.485493	0.533105	1.271854	0.051*
C7	0.66320 (4)	0.62911 (5)	0.8419 (4)	0.0371 (3)
H7	0.688522	0.647533	0.766999	0.045*
O1	0.72788 (17)	0.4980 (4)	0.437 (4)	0.151 (4)	0.4

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N5	0.0305 (5)	0.0230 (4)	0.0267 (5)	−0.0015 (4)	0.0004 (4)	0.0004 (4)
N4	0.0314 (5)	0.0229 (4)	0.0278 (5)	−0.0001 (4)	−0.0027 (4)	−0.0002 (4)
N10	0.0352 (6)	0.0318 (5)	0.0392 (6)	−0.0057 (4)	0.0071 (5)	0.0030 (5)
N11	0.0424 (6)	0.0251 (5)	0.0314 (5)	−0.0015 (4)	0.0072 (5)	0.0031 (4)
N2	0.0502 (7)	0.0275 (5)	0.0373 (6)	−0.0031 (4)	−0.0092 (5)	0.0041 (4)
C3	0.0390 (6)	0.0247 (5)	0.0269 (6)	−0.0043 (4)	−0.0015 (5)	0.0001 (4)
N12	0.0481 (7)	0.0369 (6)	0.0414 (7)	0.0072 (5)	0.0019 (5)	0.0069 (5)
N1	0.0490 (7)	0.0326 (6)	0.0496 (7)	0.0048 (5)	−0.0174 (6)	0.0015 (5)
C6	0.0318 (6)	0.0262 (5)	0.0300 (6)	−0.0032 (4)	0.0036 (5)	−0.0044 (5)
C8	0.0305 (6)	0.0402 (7)	0.0534 (9)	0.0040 (5)	−0.0083 (6)	−0.0105 (6)
C9	0.0349 (6)	0.0295 (6)	0.0402 (7)	0.0039 (5)	−0.0103 (5)	−0.0058 (5)
C13	0.0372 (6)	0.0309 (6)	0.0347 (7)	−0.0061 (5)	0.0031 (5)	0.0040 (5)
C7	0.0284 (6)	0.0368 (6)	0.0462 (8)	−0.0045 (5)	0.0029 (5)	−0.0091 (6)
O1	0.078 (3)	0.104 (4)	0.271 (13)	0.003 (4)	−0.007 (7)	0.015 (5)

Geometric parameters (Å, º)

N5—N4	1.3670 (14)	C6—C7	1.4331 (17)
N5—C6	1.3008 (15)	C8—H8	0.9300
N4—C3	1.3571 (16)	C8—C9	1.420 (2)
N4—C9	1.3769 (15)	C8—C7	1.350 (2)
N10—N11	1.2568 (16)	C13—H13A	0.9600
N10—C6	1.4161 (16)	C13—H13B	0.9600
N11—N12	1.1230 (17)	C13—H13C	0.9600
N2—C3	1.3138 (17)	C7—H7	0.9300
N2—N1	1.3887 (18)	O1—O1^i	1.342 (4)
C3—C13	1.4814 (18)	O1—O1^ii	1.343 (4)
N1—C9	1.3206 (18)
C6—N5—N4	112.72 (10)	C7—C8—H8	121.2
N5—N4—C9	127.03 (10)	C7—C8—C9	117.62 (12)
C3—N4—N5	126.09 (10)	N4—C9—C8	117.38 (12)
C3—N4—C9	106.88 (10)	N1—C9—N4	108.96 (12)
N11—N10—C6	112.97 (10)	N1—C9—C8	133.65 (12)
N12—N11—N10	173.88 (13)	C3—C13—H13A	109.5
C3—N2—N1	108.99 (11)	C3—C13—H13B	109.5
N4—C3—C13	123.47 (11)	C3—C13—H13C	109.5
N2—C3—N4	108.47 (11)	H13A—C13—H13B	109.5
N2—C3—C13	128.04 (11)	H13A—C13—H13C	109.5
C9—N1—N2	106.71 (11)	H13B—C13—H13C	109.5
N5—C6—N10	117.62 (11)	C6—C7—H7	120.5
N5—C6—C7	126.29 (12)	C8—C7—C6	118.91 (12)
N10—C6—C7	116.09 (11)	C8—C7—H7	120.5
C9—C8—H8	121.2	O1^i—O1—O1^ii	124.6 (3)
N5—N4—C3—N2	179.32 (11)	C3—N4—C9—N1	0.21 (14)
N5—N4—C3—C13	−2.43 (19)	C3—N4—C9—C8	−178.39 (12)
N5—N4—C9—N1	−179.15 (11)	C3—N2—N1—C9	0.26 (15)
N5—N4—C9—C8	2.25 (19)	N1—N2—C3—N4	−0.12 (15)
N5—C6—C7—C8	1.7 (2)	N1—N2—C3—C13	−178.28 (12)
N4—N5—C6—N10	179.85 (10)	C6—N5—N4—C3	178.94 (11)
N4—N5—C6—C7	−0.21 (17)	C6—N5—N4—C9	−1.82 (16)
N10—C6—C7—C8	−178.36 (12)	C9—N4—C3—N2	−0.05 (14)
N11—N10—C6—N5	−4.33 (16)	C9—N4—C3—C13	178.21 (11)
N11—N10—C6—C7	175.72 (11)	C9—C8—C7—C6	−1.2 (2)
N2—N1—C9—N4	−0.28 (15)	C7—C8—C9—N4	−0.55 (19)
N2—N1—C9—C8	178.00 (15)	C7—C8—C9—N1	−178.72 (15)

Symmetry codes: (i) y+1/4, −x+5/4, z+1/4; (ii) −y+5/4, x−1/4, z−1/4.

3-methyl-6-azido-1,2,4-triazolo[4,3-b]pyridazine (C6H5N7.H2Oat0_10GPa)

Crystal data

C6H5N7·0.5(O)	Dx = 1.480 Mg m^−3
Mr = 183.17	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I41/a	Cell parameters from 660 reflections
a = 28.275 (3) Å	θ = 4.1–17.9°
c = 4.1124 (12) Å	µ = 0.11 mm^−1
V = 3287.8 (12) Å^3	T = 296 K
Z = 16	Plate, colorless
F(000) = 1504	0.39 × 0.30 × 0.10 mm

Data collection

KM-4 CCD diffractometer	908 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	403 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.141
Detector resolution: 16.2413 pixels mm^-1	θmax = 26.7°, θmin = 4.3°
HP ω scans – for more details see: A. Budzianowski, A. Katrusiak in High–Pressure Crystallography (Eds.: A. Katrusiak, P. F. McMillan), Dordrecht: Kluwer Acad. Publ., 2004 pp.157–168	h = −35→35
Absorption correction: multi-scan CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −27→27
Tmin = 0.257, Tmax = 1.000	l = −3→3
6357 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
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) = 0.199	w = 1/[σ^2(Fo^2) + (0.0674P)^2 + 0.5043P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
908 reflections	Δρmax = 0.14 e Å^−3
128 parameters	Δρmin = −0.14 e Å^−3
0 restraints

Special details

Experimental. Data were collected at room temperature and pressure of 0.10 (2) GPa (100000 kPa) with the crystal obtained by the in-situ high-pressure crystallization technique. Pressure was determined by monitoring the shift of the ruby R1-fluorescence line.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
N5	0.57685 (17)	0.61849 (17)	0.8488 (15)	0.0575 (18)
N4	0.5863 (2)	0.58077 (19)	1.0439 (15)	0.0615 (18)
N10	0.6102 (2)	0.6793 (2)	0.5444 (17)	0.077 (2)
N11	0.5681 (3)	0.6874 (2)	0.4619 (17)	0.078 (2)
N2	0.5759 (3)	0.51952 (19)	1.3540 (16)	0.080 (2)
C3	0.5536 (3)	0.5525 (2)	1.1838 (19)	0.060 (2)
N12	0.5320 (3)	0.6970 (2)	0.371 (2)	0.099 (3)
N1	0.6244 (3)	0.5268 (2)	1.3218 (18)	0.091 (2)
C6	0.6149 (3)	0.6400 (2)	0.7522 (18)	0.061 (2)
C8	0.6703 (3)	0.5899 (3)	1.025 (2)	0.080 (3)
H8	0.7008	0.5807	1.0820	0.096*
C9	0.6302 (3)	0.5651 (3)	1.136 (2)	0.070 (2)
C13	0.5024 (2)	0.5595 (2)	1.1568 (19)	0.075 (2)
H13A	0.4925	0.5529	0.9380	0.113*
H13B	0.4947	0.5916	1.2111	0.113*
H13C	0.4865	0.5384	1.3036	0.113*
C7	0.6623 (2)	0.6278 (3)	0.832 (2)	0.076 (2)
H7	0.6874	0.6456	0.7524	0.092*
O1	0.7267 (7)	0.500 (2)	0.46 (2)	0.180 (10)	0.5

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N5	0.060 (4)	0.048 (3)	0.064 (6)	−0.004 (3)	0.003 (3)	−0.003 (3)
N4	0.070 (4)	0.050 (4)	0.064 (7)	−0.006 (3)	−0.006 (3)	0.000 (3)
N10	0.087 (5)	0.076 (5)	0.067 (7)	−0.011 (4)	0.015 (4)	0.010 (3)
N11	0.108 (6)	0.057 (4)	0.068 (8)	0.006 (5)	0.023 (5)	0.007 (3)
N2	0.117 (6)	0.066 (4)	0.055 (7)	0.009 (4)	−0.013 (4)	0.012 (3)
C3	0.088 (6)	0.050 (5)	0.042 (7)	−0.005 (5)	−0.004 (4)	−0.004 (3)
N12	0.127 (6)	0.102 (6)	0.069 (8)	0.021 (5)	0.005 (5)	0.012 (4)
N1	0.096 (6)	0.081 (5)	0.096 (8)	0.019 (4)	−0.024 (4)	−0.001 (4)
C6	0.063 (5)	0.062 (5)	0.058 (8)	−0.007 (4)	0.006 (4)	−0.004 (4)
C8	0.063 (5)	0.100 (6)	0.077 (9)	0.002 (5)	−0.018 (4)	−0.011 (5)
C9	0.075 (6)	0.075 (6)	0.059 (9)	0.001 (5)	−0.016 (5)	−0.013 (4)
C13	0.080 (5)	0.078 (5)	0.069 (9)	−0.010 (4)	0.015 (4)	0.008 (4)
C7	0.065 (5)	0.080 (6)	0.084 (9)	−0.008 (4)	0.006 (4)	−0.011 (4)
O1	0.131 (14)	0.156 (18)	0.25 (5)	0.01 (2)	−0.01 (3)	0.042 (16)

Geometric parameters (Å, º)

N5—N4	1.361 (6)	C6—C7	1.423 (8)
N5—C6	1.299 (7)	C8—H8	0.9300
N4—C3	1.351 (7)	C8—C9	1.410 (10)
N4—C9	1.371 (7)	C8—C7	1.352 (9)
N10—N11	1.258 (7)	C13—H13A	0.9600
N10—C6	1.408 (8)	C13—H13B	0.9600
N11—N12	1.122 (8)	C13—H13C	0.9600
N2—C3	1.325 (8)	C7—H7	0.9300
N2—N1	1.392 (7)	O1—O1^i	1.387 (18)
C3—C13	1.465 (8)	O1—O1^ii	1.387 (18)
N1—C9	1.334 (9)
C6—N5—N4	112.6 (5)	C7—C8—H8	121.6
N5—N4—C9	126.5 (6)	C7—C8—C9	116.8 (7)
C3—N4—N5	125.4 (6)	N4—C9—C8	118.5 (8)
C3—N4—C9	108.1 (6)	N1—C9—N4	108.0 (7)
N11—N10—C6	113.3 (6)	N1—C9—C8	133.5 (8)
N12—N11—N10	174.6 (8)	C3—C13—H13A	109.5
C3—N2—N1	108.3 (6)	C3—C13—H13B	109.5
N4—C3—C13	124.4 (6)	C3—C13—H13C	109.5
N2—C3—N4	108.4 (6)	H13A—C13—H13B	109.5
N2—C3—C13	127.2 (7)	H13A—C13—H13C	109.5
C9—N1—N2	107.2 (6)	H13B—C13—H13C	109.5
N5—C6—N10	118.5 (6)	C6—C7—H7	120.5
N5—C6—C7	126.6 (7)	C8—C7—C6	119.1 (7)
N10—C6—C7	114.9 (7)	C8—C7—H7	120.5
C9—C8—H8	121.6	O1^i—O1—O1^ii	123.3 (10)

Symmetry codes: (i) −y+5/4, x−1/4, z−1/4; (ii) y+1/4, −x+5/4, z+1/4.

3-methyl-6-azido-1,2,4-triazolo[4,3-b]pyridazine (C6H5N7.H2Oat0_23GPa)

Crystal data

C6H5N7·0.6(O)	Dx = 1.519 Mg m^−3
Mr = 184.77	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I41/a	Cell parameters from 419 reflections
a = 28.180 (6) Å	θ = 4.3–23.5°
c = 4.0701 (17) Å	µ = 0.11 mm^−1
V = 3232.2 (19) Å^3	T = 296 K
Z = 16	Plate, colorless
F(000) = 1517	0.39 × 0.29 × 0.12 mm

Data collection

KM-4 CCD diffractometer	614 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	296 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.236
Detector resolution: 16.2413 pixels mm^-1	θmax = 27.0°, θmin = 4.3°
HP ω scans – for more details see: A. Budzianowski, A. Katrusiak in High–Pressure Crystallography (Eds.: A. Katrusiak, P. F. McMillan), Dordrecht: Kluwer Acad. Publ., 2004 pp.157–168	h = −34→35
Absorption correction: multi-scan CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −6→6
Tmin = 0.585, Tmax = 1.000	l = −5→5
6161 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.083	H-atom parameters constrained
wR(F^2) = 0.234	w = 1/[σ^2(Fo^2) + (0.1072P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max < 0.001
614 reflections	Δρmax = 0.13 e Å^−3
128 parameters	Δρmin = −0.12 e Å^−3
0 restraints

Special details

Experimental. Data were collected at room temperature and pressure of 0.23 (2) GPa (230000 kPa) with the crystal obtained by the in-situ high-pressure crystallization technique. Pressure was determined by monitoring the shift of the ruby R1-fluorescence line.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
N5	0.5767 (4)	0.6193 (3)	0.8501 (16)	0.053 (3)
N4	0.5859 (4)	0.5810 (4)	1.0440 (19)	0.060 (3)
N10	0.6100 (4)	0.6801 (6)	0.548 (2)	0.078 (4)
N11	0.5676 (5)	0.6871 (6)	0.462 (3)	0.078 (4)
N2	0.5759 (5)	0.5204 (6)	1.359 (2)	0.078 (3)
C3	0.5528 (5)	0.5530 (6)	1.188 (2)	0.063 (4)
N12	0.5312 (5)	0.6972 (6)	0.366 (3)	0.099 (5)
N1	0.6243 (6)	0.5257 (6)	1.334 (2)	0.085 (4)
C6	0.6141 (5)	0.6409 (4)	0.748 (2)	0.055 (3)
C8	0.6706 (6)	0.5895 (5)	1.030 (3)	0.083 (4)
H8	0.701225	0.579733	1.082716	0.099*
C9	0.6298 (5)	0.5650 (6)	1.141 (3)	0.067 (5)
C13	0.5013 (4)	0.5591 (6)	1.159 (3)	0.082 (4)
H13A	0.491718	0.553426	0.936433	0.124*
H13B	0.492883	0.590905	1.220955	0.124*
H13C	0.485575	0.537013	1.301990	0.124*
C7	0.6621 (4)	0.6278 (6)	0.842 (3)	0.074 (4)
H7	0.687451	0.646372	0.771515	0.089*
O1	0.7265 (10)	0.5045 (15)	0.501 (13)	0.190 (10)	0.6

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N5	0.060 (6)	0.033 (5)	0.066 (4)	0.004 (11)	0.007 (6)	0.010 (4)
N4	0.059 (7)	0.047 (7)	0.073 (5)	−0.009 (13)	0.003 (6)	−0.004 (5)
N10	0.066 (7)	0.074 (10)	0.095 (6)	−0.011 (15)	0.021 (7)	0.000 (7)
N11	0.090 (8)	0.039 (8)	0.105 (8)	−0.003 (17)	0.016 (8)	0.014 (8)
N2	0.088 (8)	0.060 (8)	0.085 (6)	−0.012 (17)	−0.012 (6)	0.004 (6)
C3	0.085 (10)	0.046 (9)	0.057 (6)	−0.019 (18)	−0.003 (6)	0.007 (6)
N12	0.104 (9)	0.073 (10)	0.119 (8)	0.015 (15)	−0.003 (7)	0.015 (7)
N1	0.095 (10)	0.049 (8)	0.110 (7)	0.032 (18)	−0.023 (8)	0.002 (7)
C6	0.072 (9)	0.029 (7)	0.065 (6)	−0.017 (16)	0.015 (8)	0.007 (6)
C8	0.056 (8)	0.073 (11)	0.119 (8)	0.025 (17)	−0.038 (8)	−0.019 (9)
C9	0.041 (8)	0.059 (13)	0.099 (9)	−0.011 (17)	−0.011 (8)	−0.015 (9)
C13	0.061 (7)	0.074 (11)	0.112 (8)	−0.013 (16)	0.018 (6)	0.004 (8)
C7	0.036 (7)	0.069 (10)	0.117 (8)	0.028 (15)	0.002 (7)	−0.004 (8)
O1	0.15 (2)	0.20 (3)	0.22 (4)	0.06 (3)	0.02 (2)	−0.021 (18)

Geometric parameters (Å, º)

N5—N4	1.362 (12)	C6—C7	1.455 (18)
N5—C6	1.285 (15)	C8—H8	0.9300
N4—C3	1.355 (15)	C8—C9	1.416 (19)
N4—C9	1.374 (16)	C8—C7	1.344 (17)
N10—N11	1.260 (15)	C13—H13A	0.9600
N10—C6	1.376 (17)	C13—H13B	0.9600
N11—N12	1.137 (15)	C13—H13C	0.9600
N2—C3	1.33 (2)	C7—H7	0.9300
N2—N1	1.377 (16)	O1—O1^i	1.40 (3)
C3—C13	1.466 (18)	O1—O1^ii	1.40 (3)
N1—C9	1.37 (2)
C6—N5—N4	114.0 (11)	C7—C8—H8	122.3
N5—N4—C9	126.7 (13)	C7—C8—C9	115.3 (14)
C3—N4—N5	125.5 (12)	N4—C9—C8	118.7 (13)
C3—N4—C9	107.7 (11)	N1—C9—N4	109.3 (15)
N11—N10—C6	111.6 (16)	N1—C9—C8	132.0 (16)
N12—N11—N10	172.9 (17)	C3—C13—H13A	109.5
C3—N2—N1	111.8 (17)	C3—C13—H13B	109.5
N4—C3—C13	125.4 (15)	C3—C13—H13C	109.5
N2—C3—N4	107.0 (11)	H13A—C13—H13B	109.5
N2—C3—C13	127.5 (15)	H13A—C13—H13C	109.5
C9—N1—N2	104.1 (18)	H13B—C13—H13C	109.5
N5—C6—N10	120.2 (13)	C6—C7—H7	119.3
N5—C6—C7	123.9 (10)	C8—C7—C6	121.3 (16)
N10—C6—C7	115.9 (15)	C8—C7—H7	119.3
C9—C8—H8	122.3	O1^i—O1—O1^ii	122.1 (13)

Symmetry codes: (i) −y+5/4, x−1/4, z−1/4; (ii) y+1/4, −x+5/4, z+1/4.

3-methyl-6-azido-1,2,4-triazolo[4,3-b]pyridazine (C6H5N7.H2Oat0_58GPa)

Crystal data

C6H5N7·0.5(O)	Dx = 1.555 Mg m^−3
Mr = 183.17	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I41/a	Cell parameters from 601 reflections
a = 27.972 (6) Å	θ = 4.1–14.2°
c = 3.9991 (8) Å	µ = 0.12 mm^−1
V = 3129.1 (14) Å^3	T = 296 K
Z = 16	Plate, colorless
F(000) = 1504	0.38 × 0.28 × 0.10 mm

Data collection

KM-4 CCD diffractometer	1185 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	349 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.346
Detector resolution: 16.2413 pixels mm^-1	θmax = 27.2°, θmin = 4.1°
HP ω scans – for more details see: A. Budzianowski, A. Katrusiak in High–Pressure Crystallography (Eds.: A. Katrusiak, P. F. McMillan), Dordrecht: Kluwer Acad. Publ., 2004 pp.157–168	h = −33→32
Absorption correction: multi-scan CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −25→25
Tmin = 0.082, Tmax = 1.000	l = −4→4
8942 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.084	H-atom parameters constrained
wR(F^2) = 0.248	w = 1/[σ^2(Fo^2) + (0.0754P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.96	(Δ/σ)max < 0.001
1185 reflections	Δρmax = 0.22 e Å^−3
128 parameters	Δρmin = −0.18 e Å^−3
0 restraints

Special details

Experimental. Data were collected at room temperature and pressure of 0.58 (2) GPa (580000 kPa) with the crystal obtained by the in-situ high-pressure crystallization technique. Pressure was determined by monitoring the shift of the ruby R1-fluorescence line.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
N5	0.5760 (3)	0.6186 (3)	0.8505 (15)	0.051 (2)
N4	0.5862 (3)	0.5807 (3)	1.0491 (15)	0.055 (2)
N10	0.6093 (3)	0.6825 (3)	0.5467 (19)	0.073 (2)
N11	0.5666 (4)	0.6888 (3)	0.4573 (17)	0.069 (3)
N2	0.5774 (4)	0.5183 (3)	1.3655 (17)	0.073 (2)
C3	0.5538 (4)	0.5512 (4)	1.189 (2)	0.057 (3)
N12	0.5305 (4)	0.6979 (4)	0.360 (2)	0.097 (3)
N1	0.6257 (3)	0.5271 (3)	1.3321 (18)	0.078 (3)
C6	0.6145 (4)	0.6418 (4)	0.7554 (19)	0.057 (3)
C8	0.6705 (4)	0.5917 (4)	1.032 (2)	0.068 (3)
H8	0.7014	0.5829	1.0924	0.082*
C9	0.6304 (4)	0.5647 (4)	1.1405 (19)	0.064 (3)
C13	0.5011 (3)	0.5596 (3)	1.1561 (18)	0.073 (3)
H13A	0.4927	0.5605	0.9235	0.110*
H13B	0.4930	0.5895	1.2588	0.110*
H13C	0.4840	0.5342	1.2645	0.110*
C7	0.6629 (4)	0.6300 (4)	0.843 (2)	0.069 (3)
H7	0.6882	0.6486	0.7681	0.083*
O1	0.7252 (7)	0.496 (2)	0.44 (2)	0.169 (12)	0.5

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N5	0.054 (6)	0.051 (6)	0.048 (4)	−0.006 (4)	−0.003 (3)	−0.012 (3)
N4	0.068 (8)	0.044 (6)	0.055 (5)	0.010 (5)	−0.007 (4)	0.005 (4)
N10	0.084 (8)	0.054 (7)	0.081 (5)	0.000 (5)	0.008 (5)	0.020 (4)
N11	0.094 (10)	0.056 (7)	0.056 (5)	0.015 (7)	0.010 (6)	0.013 (4)
N2	0.104 (9)	0.047 (7)	0.068 (4)	0.005 (5)	−0.006 (5)	0.014 (4)
C3	0.059 (9)	0.057 (8)	0.055 (5)	−0.011 (6)	−0.001 (5)	−0.007 (5)
N12	0.101 (10)	0.101 (9)	0.090 (6)	0.027 (6)	0.003 (5)	0.011 (5)
N1	0.079 (8)	0.071 (8)	0.083 (5)	0.006 (5)	−0.017 (5)	0.009 (4)
C6	0.051 (8)	0.055 (8)	0.065 (6)	0.012 (6)	−0.012 (5)	−0.011 (5)
C8	0.046 (8)	0.077 (9)	0.082 (7)	−0.001 (6)	−0.004 (5)	−0.007 (6)
C9	0.088 (11)	0.053 (9)	0.053 (6)	−0.002 (7)	−0.016 (6)	0.001 (5)
C13	0.060 (9)	0.076 (8)	0.085 (6)	−0.012 (5)	0.016 (5)	−0.001 (5)
C7	0.068 (10)	0.061 (9)	0.078 (6)	−0.016 (6)	0.003 (5)	−0.007 (5)
O1	0.15 (2)	0.13 (2)	0.23 (4)	−0.01 (3)	−0.04 (4)	0.035 (18)

Geometric parameters (Å, º)

N5—N4	1.354 (9)	C6—C7	1.434 (11)
N5—C6	1.314 (10)	C8—H8	0.9300
N4—C3	1.349 (10)	C8—C9	1.419 (12)
N4—C9	1.366 (11)	C8—C7	1.329 (11)
N10—N11	1.260 (10)	C13—H13A	0.9600
N10—C6	1.421 (10)	C13—H13B	0.9600
N11—N12	1.112 (10)	C13—H13C	0.9600
N2—C3	1.334 (10)	C7—H7	0.9300
N2—N1	1.380 (8)	O1—O1^i	1.408 (15)
C3—C13	1.498 (10)	O1—O1^ii	1.408 (16)
N1—C9	1.310 (10)
C6—N5—N4	112.5 (7)	C7—C8—H8	120.8
N5—N4—C9	127.1 (9)	C7—C8—C9	118.4 (9)
C3—N4—N5	125.6 (9)	N4—C9—C8	117.4 (10)
C3—N4—C9	107.3 (9)	N1—C9—N4	109.2 (10)
N11—N10—C6	112.1 (8)	N1—C9—C8	133.4 (12)
N12—N11—N10	173.2 (12)	C3—C13—H13A	109.5
C3—N2—N1	108.1 (7)	C3—C13—H13B	109.5
N4—C3—C13	121.8 (10)	C3—C13—H13C	109.5
N2—C3—N4	108.0 (9)	H13A—C13—H13B	109.5
N2—C3—C13	130.0 (10)	H13A—C13—H13C	109.5
C9—N1—N2	107.4 (8)	H13B—C13—H13C	109.5
N5—C6—N10	118.8 (8)	C6—C7—H7	120.8
N5—C6—C7	126.1 (9)	C8—C7—C6	118.4 (8)
N10—C6—C7	115.1 (10)	C8—C7—H7	120.8
C9—C8—H8	120.8	O1^i—O1—O1^ii	120.3 (7)

Symmetry codes: (i) −y+5/4, x−1/4, z−1/4; (ii) y+1/4, −x+5/4, z+1/4.