In the complex [Ag(2AB)2]NO3·(2AB)2 (2AB: 2-aminobenzoxazole), the central silver atom is coordinated monodentately by two 2AB ligands forming a linear geometry. The extended structure features N—H⋯N, N—H⋯π and π–π interactions.
Keywords: crystal structure, cadmium complex, 2-aminobenzoxazole, linear geometry
Abstract
The coordination complex of 2-aminobenzaxole (2AB) with silver(I), namely, bis(2-aminobenzoxazole-κN)silver(I) nitrate–bis(2-aminobenzoxazole (1/2), [Ag(C7H6N2O)2]NO3·2C7H6N2O or [Ag(2AB)2]NO3·(2AB)2, was synthesized from ethanol solutions of AgNO3 and 2AB. The asymmetric unit contains one molecule of [Ag(2AB)2]NO3·(2AB)2, The central silver(I) atom is coordinated by two nitrogen donor atoms from 2-aminobenzaxazole ligands in an N2 coordination set while another two 2-aminobenzaxazole ligands and one nitrate anion remain uncoordinated. The crystal structure features several intramolecular N—H⋯O and N—H⋯N hydrogen-bonding interactions as well as C—H⋯π, Ag⋯π and π–π interactions between adjacent AB ligands. Hirshfeld surface analysis and two-dimensional fingerprint plots were used to investigate the intermolecular interactions.
1. Chemical context
The benzoxazole framework has been explored for its antitubercular potential since the early 19th century (Wagner & Vonderbank, 1949 ▸; Šlachtová & Brulíková, 2018 ▸). In recent decades, 2-aminobenzoxazole (2AB) has attracted considerable attention due to its structural versatility and broad spectrum of applications in pharmaceuticals because of its antibacterial (Paramashivappa et al., 2003 ▸), anti-inflammatory (Parlapalli & Manda, 2017 ▸), antitumour (Imaizumi et al., 2020 ▸), antimicrobial (Erol et al., 2022 ▸;), analgesic (Ali et al., 2022 ▸; Sattar et al., 2020 ▸) and fungicidal activities (Fan et al., 2022 ▸), as well as in agrochemicals and materials science (Potashman et al., 2007 ▸). Substituents at the 2- and 5-positions of the benzene ring have been found to significantly enhance biological activity, particularly antitubercular effects (Manna & Agrawal, 2010 ▸; Sharma et al., 2011 ▸; Shaharyar et al., 2006 ▸). Moreover, 2AB has emerged as a promising candidate in antiviral drug development, as it acts as a ligand for the internal ribosome entry site (IRES) RNA of the hepatitis C virus (Rynearson et al., 2014 ▸). In this study, we present the synthesis of a silver(I) coordination complex with 2AB, along with its crystal structure, supramolecular characteristics, and Hirshfeld surface analysis.
2. Structural commentary
The asymmetric unit of the synthesized complex consists of a single [Ag(2AB)2]NO3·(2AB)2 molecule. The central silver(I) atom is coordinated by two nitrogen donor atoms from 2-aminobenzoxazole ligands, forming an N2 coordination set in a linear geometry while another two 2-aminobenzaxazole ligands and one nitrate anion remain uncoordinated (see Fig. 1 ▸). Each 2AB ligand binds in a monodentate fashion via its neutral nitrogen atom, exhibiting Ag—N bond lengths of 2.110 (5) and 2.116 (5) Å. The dihedral angle between the two oppositely coordinated 2-aminobenzoxazole ligands is 2.55 (7)°.
Figure 1.
[Ag(2AB)2]NO3·(2AB)2 with displacement ellipsoids drawn at the 30% ellipsoid probability level showing the atom labelling. Hydrogen atoms are represented as small spheres with arbitrary radii and hydrogen bonds are indicated by dashed lines.
3. Supramolecular features
Hydrogen-bonding interactions occur between the components of the title complex. In particular, the amino groups of the two coordinated 2-aminobenzoxazole ligands interact with an oxygen and nitrogen atom of the nitrate anion through N—H⋯O and N—H⋯N interactions, while both of the uncoordinated 2-aminobenzoxazole ligands also form an N—H⋯O hydrogen bond with the nitrate anion (Table 1 ▸). Several N—H⋯N hydrogen bonds also occur. There is also an N—H⋯π interaction between the amino group and the six-membered aromatic ring of the 2-aminobenzoxazole ligand, N4—H4B⋯Cg11 (Fig. 2 ▸, Table 1 ▸). In addition both of the coordinated 2AB ligands participate in π–π interactions [Cg1⋯Cg7iv = 3.584 (4) Å, dihedral angle = 6.7 (4)°; Cg2⋯Cg4v = 3.609 (4) Å, dihedral angle = 2.5 (4)°; Cg4⋯Cg7iv = 3.953 (4) Å, dihedral angle = 6.4 (4)°; where Cg1, Cg2, Cg4 andCg7 are the centroids of the O1/C13/C8/N1/C14, O2/C6/C1/N3/C7, C8–13 and O3/C20/C15/N6/C21 rings, respectively; symmetry codes: (iv) x, y − 1, z; (v) 1 − x, −y, −z]. η2 Ag⋯π interactions are also observed involving adjacent carbon atoms of two phenyl rings. In the first ring, the Ag1⋯C8 and Ag1⋯C9 distances are 3.411 (6) and 3.186 (7) Å, respectively, while in the second ring, the Ag1⋯C16 and Ag1⋯C17 distances are 3.418 (9) and 3.345 (9) Å, respectively.
Table 1. Hydrogen-bond geometry (Å, °).
Cg11 is the centroid of the C22–C27 ring.
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| N2—H2A⋯N6i | 0.84 (2) | 2.15 (5) | 2.915 (8) | 151 (7) |
| N2—H2B⋯O5 | 0.83 (2) | 2.15 (3) | 2.937 (10) | 158 (8) |
| N2—H2B⋯O7 | 0.83 (2) | 2.65 (7) | 3.271 (10) | 133 (8) |
| N4—H4A⋯O5 | 0.85 (2) | 2.14 (4) | 2.937 (9) | 157 (9) |
| N4—H4A⋯O6 | 0.85 (2) | 2.46 (6) | 3.084 (8) | 131 (6) |
| N4—H4A⋯N5 | 0.85 (2) | 2.64 (4) | 3.434 (8) | 156 (7) |
| N7—H7A⋯O7i | 0.84 (2) | 2.17 (2) | 3.012 (9) | 175 (7) |
| N7—H7B⋯O6 | 0.85 (2) | 2.24 (3) | 3.069 (8) | 165 (8) |
| N9—H9A⋯N8ii | 0.85 (2) | 2.18 (3) | 2.997 (9) | 161 (9) |
| N9—H9B⋯O6 | 0.85 (2) | 2.28 (5) | 3.041 (10) | 149 (9) |
| N4—H4B⋯Cg11iii | 0.85 (4) | 2.58 (5) | 3.403 (7) | 162 (7) |
Symmetry codes: (i) 
; (ii) 
; (iii) 
.
Figure 2.
The packing of [Ag(2AB)2]NO3·(2AB)2 showing N—H⋯O, N—H⋯N, N—H⋯π, Ag⋯π, and π–π interactions.
4. Hirshfeld Surface Analysis
A Hirshfeld surface (HS) analysis (Spackman & Jayatilaka, 2009 ▸) was performed and the two-dimensional fingerprint plots (Spackman & McKinnon, 2002 ▸) were generated using CrystalExplorer (Spackman et al., 2021 ▸) to quantify the intermolecular interactions (Fig. 3 ▸). The red spots on the HS indicate the presence of close intermolecular N—H⋯O and N—H⋯N interactions. The fingerprint plots shows that H⋯H (31.50%), C⋯H/H⋯C (19.60%), O⋯H/H⋯O (17.2%), N⋯H/H⋯N (9.60%), C⋯C (5.30%), C⋯N/N⋯C (4.40%), C⋯O/O⋯C (3.90%), and Ag⋯C/C⋯Ag (4.20%) are the major interactions contributing ∼95.7% to the HS with minor interactions contributing less than 5%.
Figure 3.
The Hirshfeld surface and corresponding two-dimensional fingerprint plots illustrating the contributions of different intermolecular contacts.
5. Database survey
A survey of the Cambridge Structural Database (CSD, Version 5.46, November 2024; Groom et al., 2016 ▸) identified 18 crystal structures of 2-aminobenzoxazole (2AB) derivatives. Among them, only three structures (DIWPIM; Razzoqova et al., 2023 ▸, MUYZEP; Razzoqova et al., 2025 ▸, QALXIL; Decken & Gossage, 2005 ▸) were found for the 2-aminobenzoxazole moiety. Among these, one structure involves a zinc coordination complex (QALXIL), and two structures involve cadmium complexes (DIWPIM, MUYZEP). In the zinc complex QALXIL, the ZnII centre adopts a distorted tetrahedral geometry, coordinating two 2AB ligands via their aromatic nitrogen atoms, along with two chloride ligands. The cadmium complex [Cd(2AB)2(CH3COO)2] (DIWPIM) features a CdII ion coordinated by two 2AB ligands and two acetate ligands, binding in both monodentate and bidentate modes, resulting in a distorted octahedral coordination environment with an N2O4 donor set. In the complex [Cd(2AB)2(NO3)2] (MUYZEP), the cadmium(II) ion is coordinated by four 2AB ligands and two nitrate ions, forming a distorted octahedral geometry with an N4O2 coordination sphere.
6. Synthesis and crystallization
AgNO3 (0.170 g, 1 mmol) and 2AB (0.268 g, 2 mmol) were dissolved separately in ethanol (5 ml), mixed together and stirred for 2 h. The obtained colourless solution was filtered and left for crystallization. Single crystals of the complex [Ag(AB)2](NO3)(AB)2 suitable for X-ray analysis were obtained by slow evaporation of the solution over a period of 15d.
7. Refinement
Crystal data, data collection, and structure refinement details are summarized in Table 2 ▸. All hydrogen atoms were located from difference-Fourier maps and refined isotropically; DFIX restraints were applied to the N—H bond lengths.
Table 2. Experimental details.
| Crystal data | |
| Chemical formula | [Ag(C7H6N2O)2]NO3·2C7H6N2O |
| M r | 706.43 |
| Crystal system, space group | Triclinic, P
|
| Temperature (K) | 293 |
| a, b, c (Å) | 10.6356 (3), 11.2202 (5), 12.3475 (3) |
| α, β, γ (°) | 92.459 (3), 94.903 (2), 98.682 (3) |
| V (Å3) | 1448.91 (8) |
| Z | 2 |
| Radiation type | Cu Kα |
| μ (mm−1) | 6.13 |
| Crystal size (mm) | 0.11 × 0.09 × 0.08 |
| Data collection | |
| Diffractometer | XtaLAB Synergy, Single source at home/near, H |
| Absorption correction | Multi-scan (CrysAlis PRO ; Rigaku OD, 2020 ▸) |
| Tmin, Tmax | 0.332, 0.642 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 14506, 5559, 4536 |
| R int | 0.074 |
| (sin θ/λ)max (Å−1) | 0.615 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.070, 0.235, 1.12 |
| No. of reflections | 5559 |
| No. of parameters | 430 |
| No. of restraints | 12 |
| H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
| Δρmax, Δρmin (e Å−3) | 1.62, −1.69 |
Supplementary Material
Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989025010254/oo2013sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989025010254/oo2013Isup2.hkl
CCDC reference: 2502918
Additional supporting information: crystallographic information; 3D view; checkCIF report
Acknowledgments
BT would like to acknowledge TWAS–CSIR Postdoctoral Fellowship Programme and also to the Frank H. Allen International Research and Education (FAIRE) programme, provided by the Cambridge Crystallographic Data Centre (CCDC), for the opportunity to use the Cambridge Structural Database (CSD).
supplementary crystallographic information
Bis(2-aminobenzoxazole-κN)silver(I) nitrate–bis(2-aminobenzoxazole (1/2) . Crystal data
| [Ag(C7H6N2O)2]NO3·2C7H6N2O | Z = 2 |
| Mr = 706.43 | F(000) = 716 |
| Triclinic, P1 | Dx = 1.619 Mg m−3 |
| a = 10.6356 (3) Å | Cu Kα radiation, λ = 1.54184 Å |
| b = 11.2202 (5) Å | Cell parameters from 5786 reflections |
| c = 12.3475 (3) Å | θ = 3.6–71.3° |
| α = 92.459 (3)° | µ = 6.13 mm−1 |
| β = 94.903 (2)° | T = 293 K |
| γ = 98.682 (3)° | Block, colourless |
| V = 1448.91 (8) Å3 | 0.11 × 0.09 × 0.08 mm |
Bis(2-aminobenzoxazole-κN)silver(I) nitrate–bis(2-aminobenzoxazole (1/2) . Data collection
| XtaLAB Synergy, Single source at home/near, H diffractometer | 5559 independent reflections |
| Radiation source: micro-focus sealed X-ray tube | 4536 reflections with I > 2σ(I) |
| Detector resolution: 10.0000 pixels mm-1 | Rint = 0.074 |
| ω scans | θmax = 71.6°, θmin = 3.6° |
| Absorption correction: multi-scan (CrysAlisPro ; Rigaku OD, 2020) | h = −13→10 |
| Tmin = 0.332, Tmax = 0.642 | k = −13→13 |
| 14506 measured reflections | l = −15→15 |
Bis(2-aminobenzoxazole-κN)silver(I) nitrate–bis(2-aminobenzoxazole (1/2) . Refinement
| Refinement on F2 | Primary atom site location: dual |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.070 | Hydrogen site location: mixed |
| wR(F2) = 0.235 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.12 | w = 1/[σ2(Fo2) + (0.1293P)2 + 1.0923P] where P = (Fo2 + 2Fc2)/3 |
| 5559 reflections | (Δ/σ)max < 0.001 |
| 430 parameters | Δρmax = 1.62 e Å−3 |
| 12 restraints | Δρmin = −1.69 e Å−3 |
Bis(2-aminobenzoxazole-κN)silver(I) nitrate–bis(2-aminobenzoxazole (1/2) . 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. |
Bis(2-aminobenzoxazole-κN)silver(I) nitrate–bis(2-aminobenzoxazole (1/2) . Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| Ag1 | 0.42768 (4) | 0.08778 (4) | 0.14010 (4) | 0.0590 (2) | |
| O1 | 0.1314 (4) | −0.0952 (4) | −0.0925 (4) | 0.0592 (11) | |
| O2 | 0.6801 (5) | 0.3272 (4) | 0.3700 (4) | 0.0638 (12) | |
| N1 | 0.3036 (5) | −0.0216 (5) | 0.0205 (4) | 0.0484 (11) | |
| N2 | 0.1515 (7) | 0.1029 (6) | −0.0354 (7) | 0.0746 (17) | |
| H2A | 0.089 (6) | 0.090 (7) | −0.083 (6) | 0.090* | |
| H2B | 0.193 (7) | 0.170 (4) | −0.016 (7) | 0.090* | |
| N3 | 0.5661 (5) | 0.1799 (5) | 0.2604 (4) | 0.0512 (11) | |
| N4 | 0.4995 (7) | 0.3708 (6) | 0.2761 (6) | 0.0752 (18) | |
| H4A | 0.429 (5) | 0.350 (6) | 0.238 (7) | 0.090* | |
| H4B | 0.523 (7) | 0.445 (3) | 0.297 (7) | 0.090* | |
| C1 | 0.6719 (6) | 0.1359 (6) | 0.3110 (5) | 0.0521 (13) | |
| C2 | 0.7103 (7) | 0.0237 (6) | 0.3025 (6) | 0.0627 (16) | |
| H2 | 0.662384 | −0.040164 | 0.259658 | 0.075* | |
| C3 | 0.8249 (8) | 0.0118 (7) | 0.3617 (7) | 0.075 (2) | |
| H3 | 0.854698 | −0.061943 | 0.358073 | 0.090* | |
| C4 | 0.8953 (7) | 0.1069 (8) | 0.4257 (7) | 0.076 (2) | |
| H4 | 0.972577 | 0.096078 | 0.462218 | 0.092* | |
| C5 | 0.8547 (7) | 0.2175 (7) | 0.4370 (6) | 0.0670 (17) | |
| H5 | 0.900920 | 0.281153 | 0.481321 | 0.080* | |
| C6 | 0.7402 (6) | 0.2273 (6) | 0.3778 (5) | 0.0549 (14) | |
| C7 | 0.5768 (6) | 0.2919 (6) | 0.2976 (5) | 0.0543 (14) | |
| C8 | 0.3061 (6) | −0.1432 (6) | −0.0033 (5) | 0.0531 (14) | |
| C9 | 0.3949 (7) | −0.2174 (6) | 0.0292 (6) | 0.0612 (16) | |
| H9 | 0.467054 | −0.188776 | 0.076390 | 0.073* | |
| C10 | 0.3695 (9) | −0.3366 (7) | −0.0128 (7) | 0.078 (2) | |
| H10 | 0.425922 | −0.389097 | 0.007756 | 0.093* | |
| C11 | 0.2646 (10) | −0.3792 (7) | −0.0833 (8) | 0.083 (2) | |
| H11 | 0.251777 | −0.459468 | −0.109480 | 0.099* | |
| C12 | 0.1768 (8) | −0.3055 (7) | −0.1166 (6) | 0.0702 (19) | |
| H12 | 0.105417 | −0.333766 | −0.164773 | 0.084* | |
| C13 | 0.2017 (6) | −0.1878 (6) | −0.0740 (5) | 0.0574 (14) | |
| C14 | 0.1975 (6) | 0.0008 (6) | −0.0326 (5) | 0.0535 (14) | |
| O3 | 0.2193 (5) | 0.7580 (5) | 0.2610 (4) | 0.0659 (12) | |
| N6 | 0.0707 (5) | 0.8530 (5) | 0.1741 (5) | 0.0586 (13) | |
| N7 | 0.0691 (7) | 0.6442 (6) | 0.1405 (5) | 0.0709 (16) | |
| H7A | 0.013 (6) | 0.643 (7) | 0.088 (5) | 0.085* | |
| H7B | 0.125 (6) | 0.598 (6) | 0.140 (6) | 0.085* | |
| C15 | 0.1506 (7) | 0.9375 (7) | 0.2480 (5) | 0.0607 (16) | |
| C16 | 0.1538 (8) | 1.0573 (8) | 0.2688 (7) | 0.076 (2) | |
| H16 | 0.095172 | 1.098802 | 0.232582 | 0.091* | |
| C17 | 0.2475 (9) | 1.1161 (9) | 0.3460 (8) | 0.083 (2) | |
| H17 | 0.251395 | 1.198372 | 0.362370 | 0.100* | |
| C18 | 0.3339 (9) | 1.0549 (11) | 0.3983 (7) | 0.090 (3) | |
| H18 | 0.394775 | 1.096878 | 0.450410 | 0.108* | |
| C19 | 0.3348 (8) | 0.9332 (10) | 0.3771 (7) | 0.085 (2) | |
| H19 | 0.394560 | 0.892073 | 0.412464 | 0.101* | |
| C20 | 0.2420 (7) | 0.8774 (7) | 0.3007 (6) | 0.0622 (16) | |
| C21 | 0.1159 (6) | 0.7536 (6) | 0.1864 (5) | 0.0552 (14) | |
| O4 | 0.2916 (4) | 0.4227 (4) | 0.4621 (4) | 0.0620 (11) | |
| N8 | 0.1235 (5) | 0.4191 (5) | 0.5619 (4) | 0.0558 (12) | |
| N9 | 0.1122 (7) | 0.4853 (8) | 0.3811 (6) | 0.0777 (19) | |
| H9A | 0.040 (4) | 0.509 (8) | 0.382 (7) | 0.093* | |
| H9B | 0.160 (6) | 0.509 (8) | 0.332 (6) | 0.093* | |
| C22 | 0.2243 (6) | 0.3788 (5) | 0.6238 (5) | 0.0532 (13) | |
| C23 | 0.2349 (7) | 0.3414 (6) | 0.7274 (6) | 0.0624 (16) | |
| H23 | 0.166796 | 0.337238 | 0.770247 | 0.075* | |
| C24 | 0.3519 (7) | 0.3095 (7) | 0.7669 (6) | 0.0674 (18) | |
| H24 | 0.361718 | 0.285213 | 0.837797 | 0.081* | |
| C25 | 0.4530 (7) | 0.3132 (7) | 0.7036 (6) | 0.0672 (18) | |
| H25 | 0.529411 | 0.291607 | 0.732625 | 0.081* | |
| C26 | 0.4424 (7) | 0.3483 (7) | 0.5981 (7) | 0.0649 (17) | |
| H26 | 0.509288 | 0.350226 | 0.554071 | 0.078* | |
| C27 | 0.3262 (6) | 0.3804 (6) | 0.5617 (6) | 0.0566 (14) | |
| C28 | 0.1690 (6) | 0.4432 (6) | 0.4704 (6) | 0.0589 (15) | |
| O5 | 0.3017 (6) | 0.3107 (6) | 0.0929 (6) | 0.093 (2) | |
| O6 | 0.2585 (6) | 0.4664 (5) | 0.1816 (5) | 0.0798 (15) | |
| O7 | 0.1249 (6) | 0.3756 (7) | 0.0546 (7) | 0.109 (2) | |
| N5 | 0.2266 (6) | 0.3839 (6) | 0.1100 (5) | 0.0657 (15) |
Bis(2-aminobenzoxazole-κN)silver(I) nitrate–bis(2-aminobenzoxazole (1/2) . Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Ag1 | 0.0569 (4) | 0.0592 (3) | 0.0571 (3) | 0.0089 (2) | −0.0119 (2) | −0.0049 (2) |
| O1 | 0.053 (2) | 0.066 (3) | 0.056 (2) | 0.011 (2) | −0.0104 (19) | −0.004 (2) |
| O2 | 0.060 (3) | 0.054 (2) | 0.072 (3) | 0.010 (2) | −0.019 (2) | −0.010 (2) |
| N1 | 0.046 (3) | 0.051 (3) | 0.047 (3) | 0.011 (2) | −0.010 (2) | −0.004 (2) |
| N2 | 0.073 (4) | 0.058 (3) | 0.092 (5) | 0.024 (3) | −0.012 (3) | 0.000 (3) |
| N3 | 0.048 (3) | 0.049 (3) | 0.053 (3) | 0.004 (2) | −0.011 (2) | −0.004 (2) |
| N4 | 0.069 (4) | 0.065 (4) | 0.091 (5) | 0.026 (3) | −0.015 (3) | −0.015 (3) |
| C1 | 0.045 (3) | 0.055 (3) | 0.054 (3) | 0.007 (2) | −0.006 (2) | 0.006 (3) |
| C2 | 0.070 (4) | 0.055 (4) | 0.062 (4) | 0.012 (3) | −0.008 (3) | 0.003 (3) |
| C3 | 0.081 (5) | 0.067 (4) | 0.083 (5) | 0.032 (4) | 0.003 (4) | 0.015 (4) |
| C4 | 0.060 (4) | 0.089 (6) | 0.081 (5) | 0.023 (4) | −0.012 (4) | 0.017 (4) |
| C5 | 0.059 (4) | 0.068 (4) | 0.070 (4) | 0.008 (3) | −0.012 (3) | 0.002 (3) |
| C6 | 0.055 (3) | 0.057 (4) | 0.051 (3) | 0.009 (3) | −0.003 (3) | 0.005 (3) |
| C7 | 0.051 (3) | 0.052 (3) | 0.058 (3) | 0.008 (3) | −0.005 (3) | −0.001 (3) |
| C8 | 0.059 (4) | 0.051 (3) | 0.048 (3) | 0.010 (3) | 0.002 (3) | −0.001 (2) |
| C9 | 0.066 (4) | 0.060 (4) | 0.060 (4) | 0.022 (3) | 0.001 (3) | 0.002 (3) |
| C10 | 0.091 (6) | 0.065 (5) | 0.086 (5) | 0.032 (4) | 0.016 (5) | 0.016 (4) |
| C11 | 0.114 (7) | 0.051 (4) | 0.085 (6) | 0.012 (4) | 0.018 (5) | −0.009 (4) |
| C12 | 0.077 (5) | 0.070 (5) | 0.060 (4) | 0.000 (4) | 0.011 (3) | −0.010 (3) |
| C13 | 0.058 (4) | 0.060 (4) | 0.052 (3) | 0.007 (3) | −0.001 (3) | 0.000 (3) |
| C14 | 0.048 (3) | 0.058 (3) | 0.051 (3) | 0.006 (3) | −0.010 (2) | −0.003 (3) |
| O3 | 0.062 (3) | 0.081 (3) | 0.059 (3) | 0.030 (2) | −0.003 (2) | 0.012 (2) |
| N6 | 0.053 (3) | 0.067 (3) | 0.058 (3) | 0.022 (3) | −0.009 (2) | −0.004 (2) |
| N7 | 0.078 (4) | 0.067 (4) | 0.071 (4) | 0.027 (3) | −0.003 (3) | 0.005 (3) |
| C15 | 0.063 (4) | 0.072 (4) | 0.051 (3) | 0.024 (3) | 0.004 (3) | 0.002 (3) |
| C16 | 0.076 (5) | 0.078 (5) | 0.074 (5) | 0.023 (4) | 0.001 (4) | −0.009 (4) |
| C17 | 0.083 (6) | 0.077 (5) | 0.084 (6) | 0.002 (4) | 0.006 (4) | −0.014 (4) |
| C18 | 0.068 (5) | 0.120 (8) | 0.072 (5) | −0.009 (5) | 0.001 (4) | −0.021 (5) |
| C19 | 0.064 (5) | 0.119 (8) | 0.066 (5) | 0.008 (5) | −0.009 (4) | 0.016 (5) |
| C20 | 0.058 (4) | 0.079 (5) | 0.051 (3) | 0.020 (3) | −0.002 (3) | 0.006 (3) |
| C21 | 0.050 (3) | 0.067 (4) | 0.052 (3) | 0.021 (3) | 0.002 (3) | 0.004 (3) |
| O4 | 0.060 (3) | 0.073 (3) | 0.057 (2) | 0.023 (2) | 0.006 (2) | 0.003 (2) |
| N8 | 0.047 (3) | 0.063 (3) | 0.056 (3) | 0.013 (2) | −0.007 (2) | 0.000 (2) |
| N9 | 0.075 (4) | 0.103 (5) | 0.060 (4) | 0.031 (4) | −0.002 (3) | 0.018 (3) |
| C22 | 0.049 (3) | 0.050 (3) | 0.060 (3) | 0.012 (2) | −0.004 (3) | 0.001 (3) |
| C23 | 0.056 (4) | 0.064 (4) | 0.065 (4) | 0.008 (3) | −0.001 (3) | 0.001 (3) |
| C24 | 0.074 (4) | 0.064 (4) | 0.064 (4) | 0.018 (3) | −0.011 (3) | 0.007 (3) |
| C25 | 0.067 (4) | 0.066 (4) | 0.071 (4) | 0.028 (3) | −0.010 (3) | 0.000 (3) |
| C26 | 0.054 (4) | 0.067 (4) | 0.078 (5) | 0.023 (3) | 0.009 (3) | 0.000 (3) |
| C27 | 0.057 (4) | 0.052 (3) | 0.062 (4) | 0.016 (3) | −0.004 (3) | 0.003 (3) |
| C28 | 0.058 (4) | 0.058 (4) | 0.061 (4) | 0.017 (3) | −0.009 (3) | 0.003 (3) |
| O5 | 0.080 (4) | 0.077 (4) | 0.123 (5) | 0.039 (3) | −0.028 (3) | −0.023 (3) |
| O6 | 0.089 (4) | 0.080 (4) | 0.074 (3) | 0.033 (3) | −0.005 (3) | −0.005 (3) |
| O7 | 0.077 (4) | 0.098 (5) | 0.145 (6) | 0.023 (3) | −0.045 (4) | −0.002 (4) |
| N5 | 0.060 (3) | 0.066 (4) | 0.072 (4) | 0.020 (3) | −0.006 (3) | 0.010 (3) |
Bis(2-aminobenzoxazole-κN)silver(I) nitrate–bis(2-aminobenzoxazole (1/2) . Geometric parameters (Å, º)
| Ag1—N1 | 2.110 (5) | O3—C20 | 1.386 (10) |
| Ag1—N3 | 2.116 (5) | N6—C21 | 1.289 (8) |
| O1—C14 | 1.347 (8) | N6—C15 | 1.415 (9) |
| O1—C13 | 1.384 (8) | N7—C21 | 1.335 (10) |
| O2—C7 | 1.353 (8) | N7—H7A | 0.84 (2) |
| O2—C6 | 1.375 (8) | N7—H7B | 0.85 (2) |
| N1—C14 | 1.319 (8) | C15—C16 | 1.352 (11) |
| N1—C8 | 1.388 (8) | C15—C20 | 1.397 (9) |
| N2—C14 | 1.313 (9) | C16—C17 | 1.386 (12) |
| N2—H2A | 0.84 (2) | C16—H16 | 0.9300 |
| N2—H2B | 0.83 (2) | C17—C18 | 1.365 (14) |
| N3—C7 | 1.305 (8) | C17—H17 | 0.9300 |
| N3—C1 | 1.406 (8) | C18—C19 | 1.382 (15) |
| N4—C7 | 1.316 (9) | C18—H18 | 0.9300 |
| N4—H4A | 0.85 (2) | C19—C20 | 1.363 (11) |
| N4—H4B | 0.86 (2) | C19—H19 | 0.9300 |
| C1—C6 | 1.363 (9) | O4—C28 | 1.370 (8) |
| C1—C2 | 1.383 (10) | O4—C27 | 1.378 (8) |
| C2—C3 | 1.394 (10) | N8—C28 | 1.289 (9) |
| C2—H2 | 0.9300 | N8—C22 | 1.405 (7) |
| C3—C4 | 1.382 (12) | N9—C28 | 1.349 (9) |
| C3—H3 | 0.9300 | N9—H9A | 0.85 (2) |
| C4—C5 | 1.380 (11) | N9—H9B | 0.85 (2) |
| C4—H4 | 0.9300 | C22—C23 | 1.364 (9) |
| C5—C6 | 1.388 (9) | C22—C27 | 1.379 (9) |
| C5—H5 | 0.9300 | C23—C24 | 1.400 (10) |
| C8—C13 | 1.369 (10) | C23—H23 | 0.9300 |
| C8—C9 | 1.395 (9) | C24—C25 | 1.378 (11) |
| C9—C10 | 1.393 (11) | C24—H24 | 0.9300 |
| C9—H9 | 0.9300 | C25—C26 | 1.378 (11) |
| C10—C11 | 1.367 (13) | C25—H25 | 0.9300 |
| C10—H10 | 0.9300 | C26—C27 | 1.383 (9) |
| C11—C12 | 1.385 (13) | C26—H26 | 0.9300 |
| C11—H11 | 0.9300 | O5—N5 | 1.253 (8) |
| C12—C13 | 1.380 (10) | O6—N5 | 1.240 (8) |
| C12—H12 | 0.9300 | O7—N5 | 1.218 (8) |
| O3—C21 | 1.367 (8) | ||
| N1—Ag1—N3 | 172.85 (18) | N1—C14—O1 | 113.8 (5) |
| C14—O1—C13 | 104.7 (5) | C21—O3—C20 | 103.4 (5) |
| C7—O2—C6 | 104.8 (5) | C21—N6—C15 | 104.2 (5) |
| C14—N1—C8 | 105.1 (5) | C21—N7—H7A | 115 (6) |
| C14—N1—Ag1 | 129.1 (4) | C21—N7—H7B | 112 (6) |
| C8—N1—Ag1 | 124.9 (4) | H7A—N7—H7B | 121 (4) |
| C14—N2—H2A | 105 (6) | C16—C15—C20 | 120.3 (7) |
| C14—N2—H2B | 125 (6) | C16—C15—N6 | 131.9 (7) |
| H2A—N2—H2B | 125 (4) | C20—C15—N6 | 107.8 (6) |
| C7—N3—C1 | 105.3 (5) | C15—C16—C17 | 117.8 (8) |
| C7—N3—Ag1 | 127.5 (4) | C15—C16—H16 | 121.1 |
| C1—N3—Ag1 | 127.0 (4) | C17—C16—H16 | 121.1 |
| C7—N4—H4A | 121 (5) | C18—C17—C16 | 120.8 (9) |
| C7—N4—H4B | 120 (5) | C18—C17—H17 | 119.6 |
| H4A—N4—H4B | 119 (4) | C16—C17—H17 | 119.6 |
| C6—C1—C2 | 121.3 (6) | C17—C18—C19 | 122.7 (8) |
| C6—C1—N3 | 107.6 (5) | C17—C18—H18 | 118.6 |
| C2—C1—N3 | 131.2 (6) | C19—C18—H18 | 118.6 |
| C1—C2—C3 | 116.3 (7) | C20—C19—C18 | 115.3 (8) |
| C1—C2—H2 | 121.9 | C20—C19—H19 | 122.3 |
| C3—C2—H2 | 121.9 | C18—C19—H19 | 122.3 |
| C4—C3—C2 | 121.5 (7) | C19—C20—O3 | 129.0 (7) |
| C4—C3—H3 | 119.2 | C19—C20—C15 | 123.0 (8) |
| C2—C3—H3 | 119.2 | O3—C20—C15 | 108.0 (6) |
| C5—C4—C3 | 122.1 (7) | N6—C21—N7 | 128.0 (6) |
| C5—C4—H4 | 118.9 | N6—C21—O3 | 116.5 (6) |
| C3—C4—H4 | 118.9 | N7—C21—O3 | 115.3 (6) |
| C4—C5—C6 | 115.4 (7) | C28—O4—C27 | 103.6 (5) |
| C4—C5—H5 | 122.3 | C28—N8—C22 | 104.0 (5) |
| C6—C5—H5 | 122.3 | C28—N9—H9A | 122 (6) |
| C1—C6—O2 | 108.6 (5) | C28—N9—H9B | 117 (6) |
| C1—C6—C5 | 123.3 (6) | H9A—N9—H9B | 118 (4) |
| O2—C6—C5 | 128.0 (6) | C23—C22—C27 | 119.4 (6) |
| N3—C7—N4 | 128.5 (6) | C23—C22—N8 | 131.8 (6) |
| N3—C7—O2 | 113.7 (5) | C27—C22—N8 | 108.7 (5) |
| N4—C7—O2 | 117.8 (6) | C22—C23—C24 | 117.7 (7) |
| C13—C8—N1 | 108.4 (6) | C22—C23—H23 | 121.2 |
| C13—C8—C9 | 120.3 (6) | C24—C23—H23 | 121.2 |
| N1—C8—C9 | 131.3 (6) | C25—C24—C23 | 121.8 (7) |
| C10—C9—C8 | 116.4 (7) | C25—C24—H24 | 119.1 |
| C10—C9—H9 | 121.8 | C23—C24—H24 | 119.1 |
| C8—C9—H9 | 121.8 | C26—C25—C24 | 121.0 (6) |
| C11—C10—C9 | 122.3 (7) | C26—C25—H25 | 119.5 |
| C11—C10—H10 | 118.9 | C24—C25—H25 | 119.5 |
| C9—C10—H10 | 118.9 | C25—C26—C27 | 115.9 (7) |
| C10—C11—C12 | 121.5 (7) | C25—C26—H26 | 122.0 |
| C10—C11—H11 | 119.2 | C27—C26—H26 | 122.0 |
| C12—C11—H11 | 119.2 | O4—C27—C22 | 107.9 (5) |
| C13—C12—C11 | 116.0 (8) | O4—C27—C26 | 127.9 (6) |
| C13—C12—H12 | 122.0 | C22—C27—C26 | 124.2 (6) |
| C11—C12—H12 | 122.0 | N8—C28—N9 | 129.0 (6) |
| C8—C13—C12 | 123.5 (7) | N8—C28—O4 | 115.8 (5) |
| C8—C13—O1 | 108.0 (6) | N9—C28—O4 | 115.2 (6) |
| C12—C13—O1 | 128.5 (7) | O7—N5—O6 | 120.7 (7) |
| N2—C14—N1 | 128.5 (6) | O7—N5—O5 | 120.0 (7) |
| N2—C14—O1 | 117.7 (6) | O6—N5—O5 | 119.3 (6) |
| C7—N3—C1—C6 | 0.5 (7) | C8—N1—C14—O1 | −2.1 (7) |
| Ag1—N3—C1—C6 | 176.1 (4) | Ag1—N1—C14—O1 | −171.0 (4) |
| C7—N3—C1—C2 | −179.8 (7) | C13—O1—C14—N2 | 179.8 (7) |
| Ag1—N3—C1—C2 | −4.2 (11) | C13—O1—C14—N1 | 1.0 (7) |
| C6—C1—C2—C3 | −2.9 (11) | C21—N6—C15—C16 | 177.0 (8) |
| N3—C1—C2—C3 | 177.4 (7) | C21—N6—C15—C20 | 0.1 (7) |
| C1—C2—C3—C4 | 0.4 (12) | C20—C15—C16—C17 | −2.1 (12) |
| C2—C3—C4—C5 | 1.9 (13) | N6—C15—C16—C17 | −178.6 (7) |
| C3—C4—C5—C6 | −1.5 (12) | C15—C16—C17—C18 | 0.5 (13) |
| C2—C1—C6—O2 | −179.9 (6) | C16—C17—C18—C19 | 0.9 (14) |
| N3—C1—C6—O2 | −0.2 (7) | C17—C18—C19—C20 | −0.7 (13) |
| C2—C1—C6—C5 | 3.4 (11) | C18—C19—C20—O3 | 179.0 (8) |
| N3—C1—C6—C5 | −176.9 (7) | C18—C19—C20—C15 | −0.9 (12) |
| C7—O2—C6—C1 | −0.2 (7) | C21—O3—C20—C19 | −179.6 (7) |
| C7—O2—C6—C5 | 176.3 (7) | C21—O3—C20—C15 | 0.3 (7) |
| C4—C5—C6—C1 | −1.1 (11) | C16—C15—C20—C19 | 2.3 (12) |
| C4—C5—C6—O2 | −177.1 (7) | N6—C15—C20—C19 | 179.6 (7) |
| C1—N3—C7—N4 | −178.6 (8) | C16—C15—C20—O3 | −177.6 (7) |
| Ag1—N3—C7—N4 | 5.9 (11) | N6—C15—C20—O3 | −0.3 (8) |
| C1—N3—C7—O2 | −0.7 (8) | C15—N6—C21—N7 | 175.1 (7) |
| Ag1—N3—C7—O2 | −176.2 (4) | C15—N6—C21—O3 | 0.1 (8) |
| C6—O2—C7—N3 | 0.6 (8) | C20—O3—C21—N6 | −0.2 (8) |
| C6—O2—C7—N4 | 178.7 (7) | C20—O3—C21—N7 | −175.9 (6) |
| C14—N1—C8—C13 | 2.2 (7) | C28—N8—C22—C23 | 179.3 (7) |
| Ag1—N1—C8—C13 | 171.8 (4) | C28—N8—C22—C27 | −0.7 (7) |
| C14—N1—C8—C9 | 179.7 (7) | C27—C22—C23—C24 | 1.8 (10) |
| Ag1—N1—C8—C9 | −10.7 (10) | N8—C22—C23—C24 | −178.2 (7) |
| C13—C8—C9—C10 | −0.9 (10) | C22—C23—C24—C25 | −1.2 (11) |
| N1—C8—C9—C10 | −178.1 (7) | C23—C24—C25—C26 | −0.2 (12) |
| C8—C9—C10—C11 | 0.9 (12) | C24—C25—C26—C27 | 0.8 (11) |
| C9—C10—C11—C12 | −0.3 (14) | C28—O4—C27—C22 | −0.5 (7) |
| C10—C11—C12—C13 | −0.3 (12) | C28—O4—C27—C26 | −178.4 (7) |
| N1—C8—C13—C12 | 178.2 (7) | C23—C22—C27—O4 | −179.3 (6) |
| C9—C8—C13—C12 | 0.3 (11) | N8—C22—C27—O4 | 0.8 (7) |
| N1—C8—C13—O1 | −1.7 (7) | C23—C22—C27—C26 | −1.3 (10) |
| C9—C8—C13—O1 | −179.5 (6) | N8—C22—C27—C26 | 178.8 (6) |
| C11—C12—C13—C8 | 0.3 (11) | C25—C26—C27—O4 | 177.5 (7) |
| C11—C12—C13—O1 | −179.9 (7) | C25—C26—C27—C22 | −0.1 (11) |
| C14—O1—C13—C8 | 0.4 (7) | C22—N8—C28—N9 | −180.0 (8) |
| C14—O1—C13—C12 | −179.4 (7) | C22—N8—C28—O4 | 0.5 (8) |
| C8—N1—C14—N2 | 179.3 (8) | C27—O4—C28—N8 | 0.0 (8) |
| Ag1—N1—C14—N2 | 10.4 (11) | C27—O4—C28—N9 | −179.6 (7) |
Bis(2-aminobenzoxazole-κN)silver(I) nitrate–bis(2-aminobenzoxazole (1/2) . Hydrogen-bond geometry (Å, º)
Cg11 is the centroid of the C22–C27 ring.
| D—H···A | D—H | H···A | D···A | D—H···A |
| N2—H2A···N6i | 0.84 (2) | 2.15 (5) | 2.915 (8) | 151 (7) |
| N2—H2B···O5 | 0.83 (2) | 2.15 (3) | 2.937 (10) | 158 (8) |
| N2—H2B···O7 | 0.83 (2) | 2.65 (7) | 3.271 (10) | 133 (8) |
| N4—H4A···O5 | 0.85 (2) | 2.14 (4) | 2.937 (9) | 157 (9) |
| N4—H4A···O6 | 0.85 (2) | 2.46 (6) | 3.084 (8) | 131 (6) |
| N4—H4A···N5 | 0.85 (2) | 2.64 (4) | 3.434 (8) | 156 (7) |
| N7—H7A···O7i | 0.84 (2) | 2.17 (2) | 3.012 (9) | 175 (7) |
| N7—H7B···O6 | 0.85 (2) | 2.24 (3) | 3.069 (8) | 165 (8) |
| N9—H9A···N8ii | 0.85 (2) | 2.18 (3) | 2.997 (9) | 161 (9) |
| N9—H9B···O6 | 0.85 (2) | 2.28 (5) | 3.041 (10) | 149 (9) |
| N4—H4B···Cg11iii | 0.85 (4) | 2.58 (5) | 3.403 (7) | 162 (7) |
Symmetry codes: (i) −x, −y+1, −z; (ii) −x, −y+1, −z+1; (iii) −x+1, −y+1, −z+1.
pi-pi interactions
| Cg(i) | Cg(j) | distance (Å) | dihedra anglel (°) |
| 1 | 7iv | 3.584 (4) | 6.7 (4) |
| 2 | 4v | 3.609 (4) | 2.5 (4) |
| 4 | 7iv | 3.953 (4) | 6.4 (4) |
Cg1 = O1-C13-C8-N1-C14; Cg2 = O2-C6-C1-N3-C7; Cg3 = C1-C6; Cg4 = C8-13; Cg7 = O3-C20-C15-N6-C21; Cg8 = C15-C20; Cg10 = O4-C27-C22-N8-C28; Cg11 = C22 -C27;Symmetry codes: (iv) x, y-1, z; (v) 1-x, -y, -z.
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989025010254/oo2013sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989025010254/oo2013Isup2.hkl
CCDC reference: 2502918
Additional supporting information: crystallographic information; 3D view; checkCIF report