The title molecule adopts an angular conformation. In the crystal, N—H⋯O and N—H⋯N hydrogen bonds together with C—H⋯π(ring) interactions form chains extending along the a-axis direction. Additional N—H⋯O hydrogen bonds link the chains into layers parallel to (100).
Keywords: crystal structure, pyrazolylacetamide, hydrogen bond
Abstract
The title molecule, C13H16N4O, adopts an angular conformation. In the crystal a layer structure is generated by N—H⋯O and N—H⋯N hydrogen bonds together with C—H⋯π(ring) interactions. Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H⋯H (53.8%), H⋯C/C⋯H (21.7%), H⋯N/N⋯H (13.6%), and H⋯O/O⋯H (10.8%) interactions. The optimized structure calculated using density functional theory (DFT) at the B3LYP/ 6–311 G(d,p) level is compared with the experimentally determined structure in the solid state. The calculated HOMO–LUMO energy gap is 5.0452 eV.
Chemical context
Nitrogen-based structures have attracted more attention in recent years because of their interesting properties in structural and inorganic chemistry (Lahmidi et al., 2018 ▸; Chkirate et al., 2020a ▸; Taia et al., 2020 ▸; Al Ati et al., 2021 ▸). The pyrazolyl-acetamide family is important in medicinal chemistry because of the wide range of pharmacological applications (Deprez-Poulain et al., 2011 ▸) such as anti-inflammatory (Sunder et al., 2013 ▸), antimicrobial and anticancer (Jitender Dev et al., 2017 ▸) and as an anti-amoebic agent (Shukla et al., 2020 ▸). They also have antioxidant activity (Chkirate et al., 2019a ▸) and have been biologically evaluated (Yan et al., 2021 ▸). Given the wide range of therapeutic applications for such compounds, and in a continuation of the work already carried out for the synthesis of compounds resulting from 1,5-benzodiazepine (Chkirate et al., 2001 ▸, 2018 ▸, 2019b ▸, 2020b ▸, 2021 ▸; Idrissi et al., 2021 ▸) a similar approach gave the title compound, N-(2-amino-5-methylphenyl)-2-(5-methyl-1H-pyrazol-3-yl)acetamide, (I). Besides the synthesis, we also report the molecular and crystal structures along with a Hirshfeld surface analysis and a density functional theory computational calculation carried out at the B3LYP/6–311 G(d,p) level.
Structural commentary
The N2/C8/C9/O1 portion of the title molecule is planar (r.m.s. deviation = 0.0013 Å) with the mean planes of the C1–C6 and N3/N4/C10–C12 rings inclined to the above plane by 86.56 (6) and 72.84 (7)°, respectively, giving the molecule an angular shape (Fig. 1 ▸). Bond distances and angles are as expected for the given formulation.
Figure 1.
Molecular structure of the title compound with the labelling scheme. The ellipsoids are drawn at the 50% probability level.
Supramolecular features
In the crystal, inversion-related pairs of N1—H1B⋯O1, and N2—H2A⋯N1 hydrogen bonds, together with C11—H11⋯Cg2 interactions (Table 1 ▸) form chains of molecules extending along the a-axis direction (Fig. 2 ▸). The chains are connected into layers parallel to (100) by N4—H4⋯O1 hydrogen bonds (Table 1 ▸ and Fig. 3 ▸). Intermolecular interactions viewed down the c axis are shown in Fig. 3 ▸.
Table 1. Hydrogen-bond geometry (Å, °).
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| N1—H1B⋯O1i | 0.91 | 2.13 | 3.0284 (19) | 171 |
| N2—H2A⋯N1ii | 0.91 | 2.14 | 3.0354 (17) | 170 |
| C2—H2⋯O1i | 0.95 | 2.62 | 3.334 (2) | 132 |
| N4—H4⋯O1iii | 0.91 (1) | 1.99 (1) | 2.8625 (17) | 163 (2) |
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+2, -y+1, -z+1; (iii) -x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}.
Figure 2.
A portion of one chain projected onto (011) with N—H⋯O and N—H⋯N hydrogen bonds depicted, respectively, by light-purple and light-blue dashed lines. The C—H⋯π(ring) interactions are depicted by green dashed lines. Hydrogen atoms not involved in interactions have been omitted for clarity.
Figure 3.
Packing arrangement viewed along the c-axis direction of the main isomer with intermolecular interactions shown as in Fig. 2 ▸.
Hirshfeld surface analysis
The CrystalExplorer program (Turner et al., 2017 ▸) was used to investigate and visualize further the intermolecular interactions of (I). The Hirshfeld surface plotted over d norm in the range −0.6149 to 1.3177 a.u. is shown in Fig. 4 ▸ a. The electrostatic potential calculated using the STO-3G basis set at the Hartree–Fock level of theory and mapped on the Hirshfeld surface over the range ±0.05 a.u. clearly shows the positions of close intermolecular contacts in the compound (Fig. 4 ▸ b). The positive electrostatic potential (blue region) over the surface indicates hydrogen-donor potential, whereas the hydrogen-bond acceptors are represented by negative electrostatic potential (red region). The shape-index (Fig. 5 ▸) generated in the range −1 to 1 Å reveals that there are no significant π–π interactions, normally indicated by adjacent red and blue triangles.
Figure 4.
(a) View of the three-dimensional Hirshfeld surface of the title compound, plotted over d norm in the range of −0.6149 to 1.3177 a.u. (b) View of the three-dimensional Hirshfeld surface of the title compound plotted over the electrostatic potential energy in the range −0.0500 to 0.0500 a.u. using the STO-3 G basis set at the Hartree–Fock level of theory.
Figure 5.
Hirshfeld surface of the title compound plotted over shape-index.
The overall two-dimensional fingerprint plot (McKinnon et al., 2007 ▸) is shown in Fig. 6 ▸ a, while those delineated into H⋯H, H⋯C/C⋯H, H⋯N/N⋯H and H⋯O/O⋯H contacts are illustrated in Fig. 6 ▸ b–e, respectively, together with their relative contributions to the Hirshfeld surface (HS). The most important interaction is H⋯H, contributing 53.8% to the overall crystal packing, which is reflected in Fig. 6 ▸ b as widely scattered points of high density due to the large hydrogen content of the molecule, with the tip at d e = d i = 1.18 Å. In the presence of C—H interactions, the pair of characteristic wings in the fingerprint plot delineated into H⋯C/C⋯H contacts (21.7% contribution to the HS), Fig. 6 ▸ c, has the tips at d e + d i = 2.76 Å. The pair of scattered points of spikes in the fingerprint plot delineated into H⋯N/N⋯H, Fig. 6 ▸ d (13.6%), have the tips at d e + d i = 2.01 Å. Finally, the H⋯O/O⋯H contacts, Fig. 6 ▸ e, make only a 10.8% contribution to the HS and have a low-density distribution of points.
Figure 6.
The full two-dimensional fingerprint plots for the title compound, showing (a) all interactions, and those delineated into (b) H⋯H, (c) H⋯C/C⋯H, (d) H⋯N/N⋯H and (e) H⋯O/O⋯H interactions. The d i and d e values are the closest internal and external distances (in Å) from given points on the Hirshfeld surface.
Density functional theory calculations
The structure in the gas phase of the title compound was optimized by means of density functional theory. The density functional theory calculation was performed by the hybrid B3LYP method and the 6–311 G(d,p) basis-set, which is based on Becke’s model (Becke, 1993 ▸) and considers a mixture of the exact (Hartree–Fock) and density functional theory exchange utilizing the B3 functional, together with the LYP correlation functional (Lee et al., 1988 ▸). After obtaining the converged geometry, the harmonic vibrational frequencies were calculated at the same theoretical level to confirm that the number of imaginary frequencies is zero for the stationary point. Both the geometry optimization and harmonic vibrational frequency analysis of the title compound were done with the Gaussian 09 program (Frisch et al., 2009 ▸). Theoretical and experimental results related to bond lengths and angles are in good agreement and are summarized in Table 2 ▸. Calculated numerical values for the title compound including electronegativity (χ), hardness (η), ionization potential (I), dipole moment (μ), electron affinity (A), electrophilicity (ω) and softness (σ) are collated in Table 3 ▸. The electron transition from the highest occupied molecular orbital (HOMO) to the lowest unoccupied molecular orbital (LUMO) energy level is shown in Fig. 7 ▸. The HOMO and LUMO are localized in the plane extending over the whole N-(2-amino-5-methylphenyl)-2-(5-methyl-1H-pyrazol-3-yl)acetamide system. The energy band gap [ΔE = ELUMO − EHOMO] of the molecule is 5.0452 eV, and the frontier molecular orbital energies, EHOMO and ELUMO, are −5.3130 and −0.2678 eV, respectively.
Table 2. Comparison of selected (X-ray and density functional theory) bond lengths and angles (Å, °).
| X-ray | B3LYP/6–311G(d,p) | |
|---|---|---|
| N1—C1 | 1.4112 (17) | 1.4114 |
| N2—C6 | 1.4347 (17) | 1.4139 |
| N2—C8 | 1.3471 (17) | 1.3692 |
| O1—C8 | 1.2376 (16) | 1.2179 |
| N3—C10 | 1.3425 (18) | 1.3316 |
| N3—N4 | 1.3635 (19) | 1.3524 |
| N4—C12 | 1.3534 (19) | 1.3598 |
| C8—C9 | 1.5119 (18) | 1.5409 |
| C9—C10 | 1.496 (2) | 1.5007 |
| C2—C1—N1 | 121.12 (12) | 122.0542 |
| C6—C1—N1 | 120.68 (12) | 119.3119 |
| C1—C6—N2 | 119.89 (11) | 116.726 |
| C5—C6—N2 | 119.46 (12) | 123.4969 |
| O1—C8—N2 | 122.20 (12) | 125.0222 |
| N2—C8—C9 | 116.22 (11) | 114.6561 |
| O1—C8—C9 | 121.58 (12) | 120.2798 |
| N3—C10—C9 | 119.95 (13) | 120.7841 |
| N3—C10—C11 | 111.17 (12) | 110.8968 |
| C10—N3—N4 | 104.22 (12) | 104.754 |
| C12—N4—N3 | 112.76 (12) | 113.2928 |
| N4—C12—C11 | 106.48 (13) | 105.3557 |
| N4—C12—C13 | 122.33 (14) | 122.8603 |
Table 3. Calculated energies.
| Molecular Energy | Compound (I) |
|---|---|
| Total Energy TE (eV) | −21754.8403 |
| E HOMO (eV) | −5.3130 |
| E LUMO (eV) | −0.2678 |
| Gap, ΔE (eV) | 5.0452 |
| Dipole moment, μ (Debye) | 6.7706 |
| Ionization potential, I (eV) | 5.3130 |
| Electron affinity, A | 0.2678 |
| Electronegativity, χ | 2.7904 |
| Hardness, η | 2.5226 |
| Electrophilicity, index ω | 1.5433 |
| Softness, σ | 0.3964 |
| Fraction of electron transferred, ΔN | 0.8344 |
Figure 7.
The energy band gap of N-(2-amino-5-methylphenyl)-2-(5-methyl-1H-pyrazol-3-yl)acetamide.
Database survey
A search of the Cambridge Structural Database (CSD version 5.40, updated March 2020; Groom et al., 2016 ▸) with the 2-(5-methyl-1H-pyrazol-3-yl)acetamide fragment yielded multiple matches. Of these, two had an N-(2-aminophenyl) substituent comparable to (I) and they are shown in Fig. 8 ▸. The first compound (II) (refcode XITFUE; Chkirate et al., 2019c ▸) carries N-(2-{[(4-methylphenyl)methylidene]amino}phenyl) on nitrogen 2. The second one (III) (refcode YODZEZ; Chkirate et al., 2019a ▸) carries N-(2-aminophenyl) on nitrogen 2. The pyrazole ring (N3/N4/C10–C12) in XITFUE is inclined to the C1–C6 benzene ring by 70.83 (8)°. In YODZEZ, the dihedral angle between the mean planes of the 2-aminophenyl and pyrazolyl rings is 65.63 (8)°. In (I), the N2/C8/C9/O1 fragment is planar (r.m.s. deviation = 0.0013 Å) with the mean planes of the C1–C6 and N3/N4/C10–C12 rings inclined to the above plane by 86.56 (6) and 72.84 (7)°, respectively, which is approximately the same as in XITFUE, but less tilted than in YODZEZ.
Figure 8.
Structures similar to (I): (II) (CSD refcode XITFUE) and (III) (CSD refcode YODZEZ) obtained in the database search. The search fragment is indicated in blue.
Synthesis and crystallization
2 g (9.3 mmol) of (Z)-4-(2-oxopropylidene)-1,5-benzodiazepin-2-one and a stoichiometric amount of hydrazine were refluxed in ethanol (40 mL) for 2 h. After concentration of the solvent volume to 20 mL, the solution was allowed to stand; the precipitate formed was filtered off and then recrystallized in ethanol. Single crystals were obtained after recrystallization from methanol in the presence of MnCl2·4H2O, which was left at room temperature for 72 h. Yield: 70%.
Refinement
Crystal data, data collection and structure refinement details are summarized in Table 4 ▸. H atoms were included as riding contributions in idealized positions (N—H = 0.88–0.91 Å, C—H = 0.95–0.99 Å) with isotropic displacement parameters 1.2–1.5 times those of the attached atoms. Residual density observed after the initial refinement converged was identified as an isomer of the primary molecule having the C7 methyl group attached to C3 instead of to C4 and with a refined occupancy of 5%. The final model was generated with a combination of rigid group and restrained refinement to make the minor component have a comparable geometry to that of the major component.
Table 4. Experimental details.
| Crystal data | |
| Chemical formula | C13H16N4O |
| M r | 244.30 |
| Crystal system, space group | Monoclinic, P21/c |
| Temperature (K) | 150 |
| a, b, c (Å) | 7.1271 (3), 8.9295 (3), 19.2508 (7) |
| β (°) | 94.683 (1) |
| V (Å3) | 1221.06 (8) |
| Z | 4 |
| Radiation type | Mo Kα |
| μ (mm−1) | 0.09 |
| Crystal size (mm) | 0.37 × 0.26 × 0.16 |
| Data collection | |
| Diffractometer | Bruker D8 QUEST PHOTON 3 diffractometer |
| Absorption correction | Numerical (SADABS; Krause et al., 2015 ▸) |
| T min, T max | 0.93, 0.99 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 66426, 5120, 4794 |
| R int | 0.028 |
| (sin θ/λ)max (Å−1) | 0.794 |
| Refinement | |
| R[F 2 > 2σ(F 2)], wR(F 2), S | 0.067, 0.164, 1.23 |
| No. of reflections | 5120 |
| No. of parameters | 212 |
| No. of restraints | 32 |
| H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
| Δρmax, Δρmin (e Å−3) | 0.44, −0.33 |
Supplementary Material
Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S205698902100503X/dj2025sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S205698902100503X/dj2025Isup5.hkl
Supporting information file. DOI: 10.1107/S205698902100503X/dj2025Isup3.cml
CCDC reference: 2083102
Additional supporting information: crystallographic information; 3D view; checkCIF report
Acknowledgments
JTM thanks Tulane University for support of the Tulane Crystallography Laboratory. Author contribution are as follows. Conceptualization, GAA and KC; methodology, GAA; investigation, KC and NA; theoretical calculations, KC; writing (original draft) KC; writing (review and editing of the manuscript) NA; supervision, KC, EME and RA; crystal-structure determination and validation, JTM.
supplementary crystallographic information
Crystal data
| C13H16N4O | F(000) = 520 |
| Mr = 244.30 | Dx = 1.329 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| a = 7.1271 (3) Å | Cell parameters from 9878 reflections |
| b = 8.9295 (3) Å | θ = 2.5–34.4° |
| c = 19.2508 (7) Å | µ = 0.09 mm−1 |
| β = 94.683 (1)° | T = 150 K |
| V = 1221.06 (8) Å3 | Parallelepiped, colourless |
| Z = 4 | 0.37 × 0.26 × 0.16 mm |
Data collection
| Bruker D8 QUEST PHOTON 3 diffractometer | 5120 independent reflections |
| Radiation source: fine-focus sealed tube | 4794 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.028 |
| Detector resolution: 7.3910 pixels mm-1 | θmax = 34.4°, θmin = 2.5° |
| φ and ω scans | h = −11→11 |
| Absorption correction: numerical (SADABS; Krause et al., 2015) | k = −14→14 |
| Tmin = 0.93, Tmax = 0.99 | l = −30→30 |
| 66426 measured reflections |
Refinement
| Refinement on F2 | Primary atom site location: dual |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.067 | Hydrogen site location: mixed |
| wR(F2) = 0.164 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.23 | w = 1/[σ2(Fo2) + (0.0465P)2 + 0.8885P] where P = (Fo2 + 2Fc2)/3 |
| 5120 reflections | (Δ/σ)max = 0.007 |
| 212 parameters | Δρmax = 0.44 e Å−3 |
| 32 restraints | Δρmin = −0.33 e Å−3 |
Special details
| Experimental. The diffraction data were obtained from 9 sets of frames, each of width 0.5° in ω or φ, collected with scan parameters determined by the "strategy" routine in APEX3. The scan time was 15 sec/frame. |
| Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
| Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. H-atoms were included as riding contributions in idealized positions with isotropic displacement parameters 1.2 - 1.5 times those of the attached atoms. Residual density observed after the initial refinement converged was identified as an isomer of the primary molecule having the C7 methyl group attached to C3 instead of to C4 and with a refined occupancy of 5%. The final model was generated with a combination of rigid group and restrained refinement to make the minor component have a comparable geometry to that of the major component. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | Occ. (<1) | |
| O1 | 0.59624 (16) | 0.37274 (17) | 0.37033 (6) | 0.0232 (2) | 0.9480 (17) |
| N1 | 0.71759 (18) | 0.54183 (13) | 0.54033 (7) | 0.0217 (2) | 0.9480 (17) |
| H1A | 0.705685 | 0.575800 | 0.495619 | 0.032* | 0.9480 (17) |
| H1B | 0.625376 | 0.578103 | 0.565705 | 0.032* | 0.9480 (17) |
| N2 | 0.87261 (16) | 0.36438 (14) | 0.43708 (6) | 0.0194 (2) | 0.9480 (17) |
| H2A | 0.997675 | 0.386010 | 0.438829 | 0.029* | 0.9480 (17) |
| O1A | 0.611 (2) | 0.392 (4) | 0.3551 (15) | 0.0232 (2) | 0.0520 (17) |
| N1A | 0.726 (2) | 0.5270 (12) | 0.5246 (10) | 0.0217 (2) | 0.0520 (17) |
| H1C | 0.714407 | 0.560992 | 0.479901 | 0.032* | 0.0520 (17) |
| H1D | 0.634098 | 0.563294 | 0.549991 | 0.032* | 0.0520 (17) |
| N2A | 0.892 (3) | 0.379 (3) | 0.4164 (9) | 0.0194 (2) | 0.0520 (17) |
| H2C | 1.010632 | 0.408561 | 0.419618 | 0.023* | 0.0520 (17) |
| C1 | 0.71306 (17) | 0.38417 (14) | 0.54490 (7) | 0.0183 (2) | 0.9480 (17) |
| C2 | 0.63639 (19) | 0.31229 (16) | 0.60084 (8) | 0.0211 (2) | 0.9480 (17) |
| H2 | 0.581442 | 0.370326 | 0.635231 | 0.025* | 0.9480 (17) |
| C3 | 0.63985 (19) | 0.15736 (16) | 0.60656 (8) | 0.0217 (2) | 0.9480 (17) |
| H3 | 0.588038 | 0.111015 | 0.645085 | 0.026* | 0.9480 (17) |
| C4 | 0.71811 (19) | 0.06826 (15) | 0.55670 (7) | 0.0201 (2) | 0.9480 (17) |
| C5 | 0.79467 (18) | 0.13954 (15) | 0.50122 (7) | 0.0190 (2) | 0.9480 (17) |
| H5 | 0.848761 | 0.081079 | 0.466773 | 0.023* | 0.9480 (17) |
| C6 | 0.79337 (17) | 0.29531 (14) | 0.49529 (7) | 0.0173 (2) | 0.9480 (17) |
| C7 | 0.7163 (2) | −0.10021 (16) | 0.56184 (9) | 0.0267 (3) | 0.9480 (17) |
| H7A | 0.762818 | −0.143428 | 0.519718 | 0.040* | 0.9480 (17) |
| H7B | 0.587355 | −0.134775 | 0.566403 | 0.040* | 0.9480 (17) |
| H7C | 0.797458 | −0.131927 | 0.602734 | 0.040* | 0.9480 (17) |
| C8 | 0.76818 (18) | 0.39484 (15) | 0.37725 (7) | 0.0181 (2) | 0.9480 (17) |
| C9 | 0.87268 (19) | 0.45874 (17) | 0.31874 (7) | 0.0233 (3) | 0.9480 (17) |
| H9A | 1.009431 | 0.458403 | 0.332792 | 0.028* | 0.9480 (17) |
| H9B | 0.850612 | 0.394239 | 0.277043 | 0.028* | 0.9480 (17) |
| C1A | 0.7392 (15) | 0.3693 (12) | 0.5253 (6) | 0.0183 (2) | 0.0520 (17) |
| C2A | 0.664 (2) | 0.2879 (16) | 0.5780 (7) | 0.0211 (2) | 0.0520 (17) |
| H2B | 0.604271 | 0.338398 | 0.613539 | 0.025* | 0.0520 (17) |
| C3A | 0.677 (2) | 0.1325 (16) | 0.5786 (8) | 0.0217 (2) | 0.0520 (17) |
| C4A | 0.764 (2) | 0.0586 (12) | 0.5266 (9) | 0.0201 (2) | 0.0520 (17) |
| H4A | 0.773122 | −0.047555 | 0.527024 | 0.024* | 0.0520 (17) |
| C5A | 0.839 (2) | 0.1400 (14) | 0.4739 (8) | 0.0190 (2) | 0.0520 (17) |
| H5A | 0.899373 | 0.089494 | 0.438300 | 0.023* | 0.0520 (17) |
| C6A | 0.827 (2) | 0.2954 (14) | 0.4732 (7) | 0.0173 (2) | 0.0520 (17) |
| C7A | 0.603 (4) | 0.043 (3) | 0.6369 (11) | 0.0267 (3) | 0.0520 (17) |
| H7D | 0.545542 | 0.110860 | 0.669177 | 0.040* | 0.0520 (17) |
| H7E | 0.508277 | −0.028421 | 0.617575 | 0.040* | 0.0520 (17) |
| H7F | 0.706943 | −0.011442 | 0.661987 | 0.040* | 0.0520 (17) |
| C8A | 0.783 (2) | 0.415 (3) | 0.3584 (9) | 0.0181 (2) | 0.0520 (17) |
| C9A | 0.890 (3) | 0.487 (2) | 0.3025 (7) | 0.0233 (3) | 0.0520 (17) |
| H9C | 1.025101 | 0.495079 | 0.318091 | 0.028* | 0.0520 (17) |
| H9D | 0.876172 | 0.427022 | 0.259173 | 0.028* | 0.0520 (17) |
| N3 | 0.67894 (16) | 0.63909 (15) | 0.24804 (6) | 0.0255 (3) | 0.9480 (17) |
| N4 | 0.65868 (16) | 0.79091 (15) | 0.24611 (6) | 0.0252 (3) | 0.9480 (17) |
| H4 | 0.574 (3) | 0.834 (3) | 0.2145 (10) | 0.036 (6)* | 0.9480 (17) |
| C10 | 0.81137 (15) | 0.61509 (16) | 0.30054 (6) | 0.0208 (2) | 0.9480 (17) |
| C11 | 0.87425 (16) | 0.75120 (17) | 0.33163 (7) | 0.0218 (2) | 0.9480 (17) |
| H11 | 0.966736 | 0.764031 | 0.369572 | 0.026* | 0.9480 (17) |
| C12 | 0.77310 (17) | 0.86140 (17) | 0.29529 (6) | 0.0219 (3) | 0.9480 (17) |
| C13 | 0.7758 (2) | 1.0282 (2) | 0.30308 (9) | 0.0301 (3) | 0.9480 (17) |
| H13A | 0.898183 | 1.059745 | 0.325150 | 0.045* | 0.9480 (17) |
| H13B | 0.675980 | 1.059071 | 0.332152 | 0.045* | 0.9480 (17) |
| H13C | 0.754972 | 1.074905 | 0.257033 | 0.045* | 0.9480 (17) |
| N3A | 0.6378 (14) | 0.668 (2) | 0.2606 (3) | 0.0255 (3) | 0.0520 (17) |
| N4A | 0.6309 (16) | 0.819 (2) | 0.2618 (3) | 0.0252 (3) | 0.0520 (17) |
| H4B | 0.530526 | 0.868604 | 0.244696 | 0.036 (6)* | 0.0520 (17) |
| C10A | 0.8062 (14) | 0.639 (2) | 0.2901 (3) | 0.0208 (2) | 0.0520 (17) |
| C11A | 0.900 (2) | 0.773 (2) | 0.3088 (5) | 0.0218 (2) | 0.0520 (17) |
| H11B | 1.023731 | 0.780410 | 0.330902 | 0.026* | 0.0520 (17) |
| C12A | 0.783 (3) | 0.891 (2) | 0.2898 (6) | 0.0219 (3) | 0.0520 (17) |
| C13A | 0.809 (4) | 1.053 (3) | 0.2971 (9) | 0.0301 (3) | 0.0520 (17) |
| H13D | 0.934950 | 1.073535 | 0.319707 | 0.045* | 0.0520 (17) |
| H13E | 0.797247 | 1.099750 | 0.250883 | 0.045* | 0.0520 (17) |
| H13F | 0.713733 | 1.094159 | 0.325523 | 0.045* | 0.0520 (17) |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0175 (4) | 0.0273 (6) | 0.0240 (6) | −0.0023 (4) | −0.0030 (4) | 0.0038 (5) |
| N1 | 0.0196 (5) | 0.0157 (5) | 0.0292 (6) | 0.0003 (4) | −0.0008 (4) | 0.0004 (4) |
| N2 | 0.0152 (4) | 0.0210 (5) | 0.0216 (5) | −0.0027 (4) | −0.0012 (4) | 0.0056 (4) |
| O1A | 0.0175 (4) | 0.0273 (6) | 0.0240 (6) | −0.0023 (4) | −0.0030 (4) | 0.0038 (5) |
| N1A | 0.0196 (5) | 0.0157 (5) | 0.0292 (6) | 0.0003 (4) | −0.0008 (4) | 0.0004 (4) |
| N2A | 0.0152 (4) | 0.0210 (5) | 0.0216 (5) | −0.0027 (4) | −0.0012 (4) | 0.0056 (4) |
| C1 | 0.0140 (5) | 0.0165 (5) | 0.0237 (6) | −0.0001 (4) | −0.0026 (4) | 0.0018 (4) |
| C2 | 0.0183 (5) | 0.0204 (6) | 0.0245 (6) | 0.0016 (4) | 0.0020 (4) | 0.0013 (5) |
| C3 | 0.0192 (5) | 0.0217 (6) | 0.0244 (6) | −0.0005 (4) | 0.0029 (4) | 0.0049 (5) |
| C4 | 0.0185 (5) | 0.0165 (5) | 0.0250 (6) | −0.0017 (4) | −0.0003 (4) | 0.0042 (4) |
| C5 | 0.0184 (5) | 0.0170 (5) | 0.0211 (5) | −0.0004 (4) | −0.0003 (4) | 0.0012 (4) |
| C6 | 0.0153 (5) | 0.0163 (5) | 0.0200 (5) | −0.0016 (4) | −0.0012 (4) | 0.0032 (4) |
| C7 | 0.0276 (6) | 0.0175 (6) | 0.0350 (7) | −0.0023 (5) | 0.0027 (5) | 0.0061 (5) |
| C8 | 0.0183 (5) | 0.0153 (5) | 0.0204 (6) | 0.0008 (4) | 0.0000 (4) | 0.0021 (4) |
| C9 | 0.0233 (6) | 0.0237 (6) | 0.0233 (6) | 0.0026 (5) | 0.0052 (5) | 0.0059 (5) |
| C1A | 0.0140 (5) | 0.0165 (5) | 0.0237 (6) | −0.0001 (4) | −0.0026 (4) | 0.0018 (4) |
| C2A | 0.0183 (5) | 0.0204 (6) | 0.0245 (6) | 0.0016 (4) | 0.0020 (4) | 0.0013 (5) |
| C3A | 0.0192 (5) | 0.0217 (6) | 0.0244 (6) | −0.0005 (4) | 0.0029 (4) | 0.0049 (5) |
| C4A | 0.0185 (5) | 0.0165 (5) | 0.0250 (6) | −0.0017 (4) | −0.0003 (4) | 0.0042 (4) |
| C5A | 0.0184 (5) | 0.0170 (5) | 0.0211 (5) | −0.0004 (4) | −0.0003 (4) | 0.0012 (4) |
| C6A | 0.0153 (5) | 0.0163 (5) | 0.0200 (5) | −0.0016 (4) | −0.0012 (4) | 0.0032 (4) |
| C7A | 0.0276 (6) | 0.0175 (6) | 0.0350 (7) | −0.0023 (5) | 0.0027 (5) | 0.0061 (5) |
| C8A | 0.0183 (5) | 0.0153 (5) | 0.0204 (6) | 0.0008 (4) | 0.0000 (4) | 0.0021 (4) |
| C9A | 0.0233 (6) | 0.0237 (6) | 0.0233 (6) | 0.0026 (5) | 0.0052 (5) | 0.0059 (5) |
| N3 | 0.0249 (6) | 0.0251 (6) | 0.0254 (5) | 0.0008 (4) | −0.0042 (4) | 0.0001 (4) |
| N4 | 0.0234 (5) | 0.0266 (6) | 0.0244 (6) | 0.0024 (4) | −0.0054 (4) | 0.0024 (5) |
| C10 | 0.0180 (5) | 0.0231 (6) | 0.0210 (5) | 0.0005 (4) | 0.0003 (4) | 0.0049 (4) |
| C11 | 0.0175 (5) | 0.0257 (6) | 0.0213 (6) | 0.0004 (4) | −0.0027 (4) | 0.0026 (5) |
| C12 | 0.0179 (5) | 0.0232 (7) | 0.0243 (6) | 0.0012 (5) | 0.0005 (4) | 0.0033 (5) |
| C13 | 0.0283 (8) | 0.0251 (7) | 0.0368 (8) | 0.0005 (6) | 0.0012 (6) | 0.0012 (6) |
| N3A | 0.0249 (6) | 0.0251 (6) | 0.0254 (5) | 0.0008 (4) | −0.0042 (4) | 0.0001 (4) |
| N4A | 0.0234 (5) | 0.0266 (6) | 0.0244 (6) | 0.0024 (4) | −0.0054 (4) | 0.0024 (5) |
| C10A | 0.0180 (5) | 0.0231 (6) | 0.0210 (5) | 0.0005 (4) | 0.0003 (4) | 0.0049 (4) |
| C11A | 0.0175 (5) | 0.0257 (6) | 0.0213 (6) | 0.0004 (4) | −0.0027 (4) | 0.0026 (5) |
| C12A | 0.0179 (5) | 0.0232 (7) | 0.0243 (6) | 0.0012 (5) | 0.0005 (4) | 0.0033 (5) |
| C13A | 0.0283 (8) | 0.0251 (7) | 0.0368 (8) | 0.0005 (6) | 0.0012 (6) | 0.0012 (6) |
Geometric parameters (Å, º)
| O1—C8 | 1.2376 (16) | C3A—C4A | 1.3900 |
| N1—C1 | 1.4112 (17) | C3A—C7A | 1.508 (3) |
| N1—H1A | 0.9099 | C4A—C5A | 1.3900 |
| N1—H1B | 0.9099 | C4A—H4A | 0.9500 |
| N2—C8 | 1.3471 (17) | C5A—C6A | 1.3900 |
| N2—C6 | 1.4347 (17) | C5A—H5A | 0.9500 |
| N2—H2A | 0.9100 | C7A—H7D | 0.9800 |
| O1A—C8A | 1.238 (3) | C7A—H7E | 0.9800 |
| N1A—C1A | 1.412 (3) | C7A—H7F | 0.9800 |
| N1A—H1C | 0.9099 | C8A—C9A | 1.511 (3) |
| N1A—H1D | 0.9100 | C9A—C10A | 1.496 (3) |
| N2A—C8A | 1.347 (3) | C9A—H9C | 0.9900 |
| N2A—C6A | 1.434 (3) | C9A—H9D | 0.9900 |
| N2A—H2C | 0.8800 | N3—C10 | 1.3425 (18) |
| C1—C6 | 1.3995 (19) | N3—N4 | 1.3635 (19) |
| C1—C2 | 1.4022 (19) | N4—C12 | 1.3534 (19) |
| C2—C3 | 1.388 (2) | N4—H4 | 0.907 (9) |
| C2—H2 | 0.9500 | C10—C11 | 1.412 (2) |
| C3—C4 | 1.397 (2) | C11—C12 | 1.3766 (19) |
| C3—H3 | 0.9500 | C11—H11 | 0.9500 |
| C4—C5 | 1.3925 (18) | C12—C13 | 1.497 (2) |
| C4—C7 | 1.5077 (19) | C13—H13A | 0.9800 |
| C5—C6 | 1.3956 (18) | C13—H13B | 0.9800 |
| C5—H5 | 0.9500 | C13—H13C | 0.9800 |
| C7—H7A | 0.9800 | N3A—C10A | 1.311 (12) |
| C7—H7B | 0.9800 | N3A—N4A | 1.351 (17) |
| C7—H7C | 0.9800 | N4A—C12A | 1.331 (16) |
| C8—C9 | 1.5119 (18) | N4A—H4B | 0.8800 |
| C9—C10 | 1.496 (2) | C10A—C11A | 1.397 (16) |
| C9—H9A | 0.9900 | C11A—C12A | 1.375 (17) |
| C9—H9B | 0.9900 | C11A—H11B | 0.9500 |
| C1A—C2A | 1.3900 | C12A—C13A | 1.468 (17) |
| C1A—C6A | 1.3900 | C13A—H13D | 0.9800 |
| C2A—C3A | 1.3900 | C13A—H13E | 0.9800 |
| C2A—H2B | 0.9500 | C13A—H13F | 0.9800 |
| C1—N1—H1A | 113.0 | C6A—C5A—H5A | 120.0 |
| C1—N1—H1B | 107.5 | C4A—C5A—H5A | 120.0 |
| H1A—N1—H1B | 111.9 | C5A—C6A—C1A | 120.0 |
| C8—N2—C6 | 121.97 (11) | C5A—C6A—N2A | 120.1 (13) |
| C8—N2—H2A | 117.4 | C1A—C6A—N2A | 119.7 (13) |
| C6—N2—H2A | 120.6 | C3A—C7A—H7D | 109.5 |
| C1A—N1A—H1C | 110.0 | C3A—C7A—H7E | 109.5 |
| C1A—N1A—H1D | 113.5 | H7D—C7A—H7E | 109.5 |
| H1C—N1A—H1D | 111.9 | C3A—C7A—H7F | 109.5 |
| C8A—N2A—C6A | 123.6 (15) | H7D—C7A—H7F | 109.5 |
| C8A—N2A—H2C | 118.2 | H7E—C7A—H7F | 109.5 |
| C6A—N2A—H2C | 118.2 | O1A—C8A—N2A | 120.4 (18) |
| C6—C1—C2 | 118.12 (12) | O1A—C8A—C9A | 126 (2) |
| C6—C1—N1 | 120.68 (12) | N2A—C8A—C9A | 113.7 (11) |
| C2—C1—N1 | 121.12 (12) | C10A—C9A—C8A | 106.6 (14) |
| C3—C2—C1 | 120.77 (13) | C10A—C9A—H9C | 110.4 |
| C3—C2—H2 | 119.6 | C8A—C9A—H9C | 110.4 |
| C1—C2—H2 | 119.6 | C10A—C9A—H9D | 110.4 |
| C2—C3—C4 | 121.24 (13) | C8A—C9A—H9D | 110.4 |
| C2—C3—H3 | 119.4 | H9C—C9A—H9D | 108.6 |
| C4—C3—H3 | 119.4 | C10—N3—N4 | 104.22 (12) |
| C5—C4—C3 | 118.03 (12) | C12—N4—N3 | 112.76 (12) |
| C5—C4—C7 | 120.82 (13) | C12—N4—H4 | 126.7 (16) |
| C3—C4—C7 | 121.13 (13) | N3—N4—H4 | 120.5 (16) |
| C4—C5—C6 | 121.19 (12) | N3—C10—C11 | 111.17 (12) |
| C4—C5—H5 | 119.4 | N3—C10—C9 | 119.95 (13) |
| C6—C5—H5 | 119.4 | C11—C10—C9 | 128.88 (12) |
| C5—C6—C1 | 120.64 (12) | C12—C11—C10 | 105.37 (12) |
| C5—C6—N2 | 119.46 (12) | C12—C11—H11 | 127.3 |
| C1—C6—N2 | 119.89 (11) | C10—C11—H11 | 127.3 |
| C4—C7—H7A | 109.5 | N4—C12—C11 | 106.48 (13) |
| C4—C7—H7B | 109.5 | N4—C12—C13 | 122.33 (14) |
| H7A—C7—H7B | 109.5 | C11—C12—C13 | 131.18 (14) |
| C4—C7—H7C | 109.5 | C12—C13—H13A | 109.5 |
| H7A—C7—H7C | 109.5 | C12—C13—H13B | 109.5 |
| H7B—C7—H7C | 109.5 | H13A—C13—H13B | 109.5 |
| O1—C8—N2 | 122.20 (12) | C12—C13—H13C | 109.5 |
| O1—C8—C9 | 121.58 (12) | H13A—C13—H13C | 109.5 |
| N2—C8—C9 | 116.22 (11) | H13B—C13—H13C | 109.5 |
| C10—C9—C8 | 111.99 (9) | C10A—N3A—N4A | 102.8 (12) |
| C10—C9—H9A | 109.2 | C12A—N4A—N3A | 117.0 (13) |
| C8—C9—H9A | 109.2 | C12A—N4A—H4B | 121.5 |
| C10—C9—H9B | 109.2 | N3A—N4A—H4B | 121.5 |
| C8—C9—H9B | 109.2 | N3A—C10A—C11A | 110.3 (14) |
| H9A—C9—H9B | 107.9 | N3A—C10A—C9A | 125.8 (16) |
| C2A—C1A—C6A | 120.0 | C11A—C10A—C9A | 123.9 (14) |
| C2A—C1A—N1A | 119.99 (8) | C12A—C11A—C10A | 108.4 (13) |
| C6A—C1A—N1A | 120.01 (8) | C12A—C11A—H11B | 125.8 |
| C1A—C2A—C3A | 120.0 | C10A—C11A—H11B | 125.8 |
| C1A—C2A—H2B | 120.0 | N4A—C12A—C11A | 101.4 (13) |
| C3A—C2A—H2B | 120.0 | N4A—C12A—C13A | 127.2 (19) |
| C4A—C3A—C2A | 120.0 | C11A—C12A—C13A | 131.3 (18) |
| C4A—C3A—C7A | 119.3 (14) | C12A—C13A—H13D | 109.5 |
| C2A—C3A—C7A | 120.6 (14) | C12A—C13A—H13E | 109.5 |
| C3A—C4A—C5A | 120.0 | H13D—C13A—H13E | 109.5 |
| C3A—C4A—H4A | 120.0 | C12A—C13A—H13F | 109.5 |
| C5A—C4A—H4A | 120.0 | H13D—C13A—H13F | 109.5 |
| C6A—C5A—C4A | 120.0 | H13E—C13A—H13F | 109.5 |
| C6—C1—C2—C3 | −0.18 (19) | C2A—C1A—C6A—N2A | 175.7 (15) |
| N1—C1—C2—C3 | −177.18 (12) | N1A—C1A—C6A—N2A | −4.3 (15) |
| C1—C2—C3—C4 | −0.5 (2) | C8A—N2A—C6A—C5A | 90 (3) |
| C2—C3—C4—C5 | 0.6 (2) | C8A—N2A—C6A—C1A | −86 (3) |
| C2—C3—C4—C7 | −178.08 (13) | C6A—N2A—C8A—O1A | 9 (5) |
| C3—C4—C5—C6 | −0.09 (19) | C6A—N2A—C8A—C9A | −173 (2) |
| C7—C4—C5—C6 | 178.64 (13) | O1A—C8A—C9A—C10A | 59 (4) |
| C4—C5—C6—C1 | −0.60 (19) | N2A—C8A—C9A—C10A | −119 (2) |
| C4—C5—C6—N2 | −179.60 (11) | C10—N3—N4—C12 | −0.05 (3) |
| C2—C1—C6—C5 | 0.73 (18) | N4—N3—C10—C11 | 0.05 (2) |
| N1—C1—C6—C5 | 177.74 (12) | N4—N3—C10—C9 | −179.92 (3) |
| C2—C1—C6—N2 | 179.72 (11) | C8—C9—C10—N3 | −95.38 (12) |
| N1—C1—C6—N2 | −3.27 (18) | C8—C9—C10—C11 | 84.65 (12) |
| C8—N2—C6—C5 | 90.79 (16) | N3—C10—C11—C12 | −0.04 (4) |
| C8—N2—C6—C1 | −88.21 (16) | C9—C10—C11—C12 | 179.93 (5) |
| C6—N2—C8—O1 | 4.1 (2) | N3—N4—C12—C11 | 0.02 (5) |
| C6—N2—C8—C9 | −176.27 (12) | N3—N4—C12—C13 | 179.89 (4) |
| O1—C8—C9—C10 | 64.49 (19) | C10—C11—C12—N4 | 0.01 (5) |
| N2—C8—C9—C10 | −115.16 (14) | C10—C11—C12—C13 | −179.84 (5) |
| C6A—C1A—C2A—C3A | 0.0 | C10A—N3A—N4A—C12A | 0.00 (3) |
| N1A—C1A—C2A—C3A | 180.0 | N4A—N3A—C10A—C11A | 0.00 (3) |
| C1A—C2A—C3A—C4A | 0.0 | N4A—N3A—C10A—C9A | 180.00 (4) |
| C1A—C2A—C3A—C7A | 177.6 (19) | C8A—C9A—C10A—N3A | −69.6 (15) |
| C2A—C3A—C4A—C5A | 0.0 | C8A—C9A—C10A—C11A | 110.4 (15) |
| C7A—C3A—C4A—C5A | −177.6 (18) | N3A—C10A—C11A—C12A | 0.00 (5) |
| C3A—C4A—C5A—C6A | 0.0 | C9A—C10A—C11A—C12A | 179.99 (6) |
| C4A—C5A—C6A—C1A | 0.0 | N3A—N4A—C12A—C11A | 0.00 (5) |
| C4A—C5A—C6A—N2A | −175.7 (15) | N3A—N4A—C12A—C13A | 180.00 (5) |
| C2A—C1A—C6A—C5A | 0.0 | C10A—C11A—C12A—N4A | 0.00 (6) |
| N1A—C1A—C6A—C5A | 180.0 | C10A—C11A—C12A—C13A | 180.00 (6) |
Hydrogen-bond geometry (Å, º)
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1B···O1i | 0.91 | 2.13 | 3.0284 (19) | 171 |
| N2—H2A···N1ii | 0.91 | 2.14 | 3.0354 (17) | 170 |
| C2—H2···O1i | 0.95 | 2.62 | 3.334 (2) | 132 |
| N4—H4···O1iii | 0.91 (1) | 1.99 (1) | 2.8625 (17) | 163 (2) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, −y+1, −z+1; (iii) −x+1, y+1/2, −z+1/2.
References
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S205698902100503X/dj2025sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S205698902100503X/dj2025Isup5.hkl
Supporting information file. DOI: 10.1107/S205698902100503X/dj2025Isup3.cml
CCDC reference: 2083102
Additional supporting information: crystallographic information; 3D view; checkCIF report