In the title compound, proton transfer from oxalic acid to the N atom of the heterocycle has occurred to form a 2:1 molecular salt. In the extended structure, N—H⋯O hydrogen bonds link the components into [100] chains, which feature R 2 2(8) and R 4 4(14) loops.
Keywords: crystal structure, 2-aminobenzoxazole, molecular structure, co-crystal, hydrogen bonds
Abstract
In the title compound, 2C7H7N2O+·C2O4
2−, proton transfer from oxalic acid to the N atom of the heterocycle has occurred to form a 2:1 molecular salt. In the extended structure, N—H⋯O hydrogen bonds link the components into [100] chains, which feature R
2
2(8) and R
4
4(14) loops.
Structure description
2-Aminobenzoxazole has gained significant attention in the field of organic chemistry due to its diverse range of applications and properties. This heterocyclic compound exhibits intriguing structural features and has demonstrated potential utility in the development of pharmaceuticals and agrochemicals and in materials science (Hwang et al., 2006 ▸; Potashman et al., 2007 ▸). With its aromatic and nitrogen-containing structural motifs, 2-aminobenzoxazole has emerged as a key scaffold for the synthesis of biologically active molecules and advanced materials. Herein, we report on the crystal structure analysis of a new 2-aminobenzoxazole–oxalic acid molecular salt.
The title organic salt crystallizes in the monoclinic space group P21/n. The molecular structure of the organic salt is shown in Fig. 1 ▸. The geometric parameters of the arene and oxazole rings are similar to standard values and to those in other related structures (Ashurov et al., 2011 ▸, 2015 ▸; Wang et al., 2016 ▸). In the oxalate (OXL) part of the organic salt, two hydrogen atoms are transferred to the nitrogen of the oxazole fragments, as in other 2-aminobenzoxazole (2ABO) structures (Nandy et al., 2016 ▸; Razzoqova et al., 2022 ▸, 2023 ▸). As a result, the 2ABO and OXL ions form two closed eight-membered rings with an
(8) graph-set notation (Etter et al., 1990 ▸). This represents a 1:2 acid-base association (Calva et al., 2011 ▸), with the first ring formed by N1—H1⋯O4 and N2—H2B⋯O3 hydrogen bonds and the second by N4—H4B⋯O6 and N3—H3A⋯O5 hydrogen bonds (Table 1 ▸). N2—H2A⋯O4 and N4—H4A⋯O5 hydrogen bonds further link the components into [100] chains, thereby forming a 14-membered ring with an
(14) graph-set motif (Fig. 2 ▸) (Etter et al., 1990 ▸). The chains are shown in Fig. 3 ▸.
Figure 1.
The organic salt structure of 2ABO and OXL. Displacement ellipsoids are drawn at the 50% probability level and N—H⋯O hydrogen bonds are shown as dashed lines.
Table 1. Hydrogen-bond geometry (Å, °).
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| N1—H1⋯O4 | 0.88 (1) | 1.78 (1) | 2.650 (2) | 176 (3) |
| N2—H2A⋯O4i | 0.87 (1) | 2.00 (1) | 2.863 (2) | 174 (3) |
| N2—H2B⋯O3 | 0.86 (1) | 1.94 (1) | 2.770 (2) | 164 (2) |
| C2—H2⋯O1ii | 0.93 | 2.65 | 3.522 (2) | 157 |
| N3—H3A⋯O5 | 0.88 (1) | 1.71 (1) | 2.577 (2) | 173 (3) |
| N4—H4A⋯O5ii | 0.87 (1) | 2.06 (1) | 2.918 (2) | 172 (2) |
| N4—H4B⋯O6 | 0.86 (1) | 2.02 (1) | 2.851 (2) | 163 (2) |
Symmetry codes: (i)
; (ii)
.
Figure 2.
The crystal structure of the organic salt structure of 2ABO and OXL viewed along the c axis.
Figure 3.
A fragment of a [100] chain in the extended structure of the title compound with hydrogen bonds shown as dashed lines.
The identification of the co-crystal as a salt is based on the successful refinement of the relevant H atoms using X-ray data. The proton transfer is further supported by the C—O distances [O4—C15 = 1.266 (2) Å, O3—C15 = 1.234 (2) Å, O5—C16 = 1.272 (2) Å and O6—C16 = 1.222 (2) Å] with differences between the bond lengths within each group of 0.032 and 0.050 Å; these differences differ from those for O—C distances in deprotonated carboxyl groups. In non-deprotonated oxalic acid, these differences are greater (Sasaki et al., 2020 ▸). The mean planes of the carboxylic fragments in the OXL ion are turned by 10.13 (4)° from each other. In the crystal, the 2BAO and OXL ions are not coplanar, the 2ABO ions being inclined to the OXL ions by 18.81 (3) and 16.00 (5)°. The dihedral angle between the 2ABO ions is 37.52 (2)°.
Synthesis and crystallization
A 2:1 stoichiometric ratio of 2-aminobenzoxazole (0.268 g, 2.0 mmol) and oxalic acid (0.090 g, 1.0 mmol) was dissolved and mixed well in distilled water (5 ml). The mixture was stirred at room temperature for 30 minutes. The solution was then transferred to a vial with small holes in the cover to allow for evaporation. After about 3 weeks, cube-like single crystals of the title salt suitable for data collection were obtained.
Refinement
Crystal data, data collection and structure refinement details are summarized in Table 2 ▸.
Table 2. Experimental details.
| Crystal data | |
| Chemical formula | 2C7H7N2O+·C2O4 2− |
| M r | 358.31 |
| Crystal system, space group | Monoclinic, P21/n |
| Temperature (K) | 293 |
| a, b, c (Å) | 6.5080 (2), 17.6943 (7), 13.6264 (5) |
| β (°) | 100.200 (4) |
| V (Å3) | 1544.34 (10) |
| Z | 4 |
| Radiation type | Cu Kα |
| μ (mm−1) | 1.03 |
| Crystal size (mm) | 0.17 × 0.14 × 0.12 |
| Data collection | |
| Diffractometer | XtaLAB Synergy, Single source at home/near, HyPix3000 |
| Absorption correction | Multi-scan (CrysAlis PRO; Rigaku OD, 2020 ▸) |
| T min, T max | 0.157, 1.000 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 2960, 2960, 2288 |
| R int | 0.031 |
| (sin θ/λ)max (Å−1) | 0.615 |
| Refinement | |
| R[F 2 > 2σ(F 2)], wR(F 2), S | 0.045, 0.132, 1.04 |
| No. of reflections | 2960 |
| No. of parameters | 259 |
| No. of restraints | 6 |
| H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
| Δρmax, Δρmin (e Å−3) | 0.23, −0.20 |
Supplementary Material
Crystal structure: contains datablock(s) I. DOI: 10.1107/S2414314624000336/bv4051sup1.cif
Supporting information file. DOI: 10.1107/S2414314624000336/bv4051Isup2.cml
CCDC reference: 2324364
Additional supporting information: crystallographic information; 3D view; checkCIF report
full crystallographic data
Crystal data
| 2C7H7N2O+·C2O42− | F(000) = 744 |
| Mr = 358.31 | Dx = 1.541 Mg m−3 |
| Monoclinic, P21/n | Cu Kα radiation, λ = 1.54184 Å |
| a = 6.5080 (2) Å | Cell parameters from 2449 reflections |
| b = 17.6943 (7) Å | θ = 4.1–70.3° |
| c = 13.6264 (5) Å | µ = 1.03 mm−1 |
| β = 100.200 (4)° | T = 293 K |
| V = 1544.34 (10) Å3 | Needle, light yellow |
| Z = 4 | 0.17 × 0.14 × 0.12 mm |
Data collection
| XtaLAB Synergy, Single source at home/near, HyPix3000 diffractometer | 2960 independent reflections |
| Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source | 2288 reflections with I > 2σ(I) |
| Mirror monochromator | Rint = 0.031 |
| Detector resolution: 10.0000 pixels mm-1 | θmax = 71.4°, θmin = 4.1° |
| ω scans | h = −8→7 |
| Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2020) | k = −20→21 |
| Tmin = 0.157, Tmax = 1.000 | l = −13→16 |
| 2960 measured reflections |
Refinement
| Refinement on F2 | Primary atom site location: dual |
| Least-squares matrix: full | Hydrogen site location: mixed |
| R[F2 > 2σ(F2)] = 0.045 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.132 | w = 1/[σ2(Fo2) + (0.0724P)2 + 0.1538P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.03 | (Δ/σ)max < 0.001 |
| 2960 reflections | Δρmax = 0.23 e Å−3 |
| 259 parameters | Δρmin = −0.20 e Å−3 |
| 6 restraints |
Special details
| Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
| Refinement. The hydrogen atoms of amino groups and protonated nitrogen atoms of oxzole groups were located in difference - Fourier maps and refined with restrained distances of 0.85±(1) Å. The H atoms of the benzene ring were calculated geometrically with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| O1 | 0.1212 (2) | 0.44529 (8) | 0.33805 (10) | 0.0428 (3) | |
| N1 | 0.4453 (2) | 0.48755 (9) | 0.38019 (11) | 0.0381 (4) | |
| H1 | 0.545 (3) | 0.5203 (13) | 0.3995 (19) | 0.082 (9)* | |
| C1 | 0.4597 (3) | 0.41299 (11) | 0.34764 (13) | 0.0366 (4) | |
| O2 | 1.3397 (2) | 0.94256 (8) | 0.42539 (10) | 0.0410 (3) | |
| N2 | 0.1639 (3) | 0.56637 (11) | 0.39934 (16) | 0.0521 (5) | |
| H2A | 0.0351 (19) | 0.5701 (15) | 0.4069 (18) | 0.069 (8)* | |
| H2B | 0.252 (3) | 0.6021 (11) | 0.4168 (18) | 0.069 (8)* | |
| C2 | 0.6255 (3) | 0.36637 (12) | 0.34088 (15) | 0.0439 (5) | |
| H2 | 0.762934 | 0.382283 | 0.360114 | 0.053* | |
| O3 | 0.4839 (2) | 0.67161 (8) | 0.42640 (12) | 0.0540 (4) | |
| N3 | 1.0284 (2) | 0.88951 (9) | 0.42134 (12) | 0.0381 (4) | |
| H3A | 0.927 (3) | 0.8578 (14) | 0.427 (2) | 0.090 (10)* | |
| C3 | 0.5769 (4) | 0.29442 (12) | 0.30389 (16) | 0.0518 (5) | |
| H3 | 0.685094 | 0.261048 | 0.299092 | 0.062* | |
| O4 | 0.7441 (2) | 0.58949 (7) | 0.42948 (10) | 0.0432 (3) | |
| N4 | 1.3345 (3) | 0.81860 (10) | 0.47545 (14) | 0.0470 (4) | |
| H4A | 1.4629 (19) | 0.8123 (15) | 0.4680 (17) | 0.061 (7)* | |
| H4B | 1.258 (3) | 0.7797 (10) | 0.4805 (18) | 0.064 (8)* | |
| C4 | 0.3719 (4) | 0.27030 (13) | 0.27364 (17) | 0.0533 (6) | |
| H4 | 0.346243 | 0.222044 | 0.247253 | 0.064* | |
| O5 | 0.7522 (2) | 0.78759 (8) | 0.43539 (12) | 0.0517 (4) | |
| C5 | 0.2049 (3) | 0.31731 (12) | 0.28231 (16) | 0.0497 (5) | |
| H5 | 0.066961 | 0.301904 | 0.263314 | 0.060* | |
| O6 | 1.0164 (2) | 0.70685 (9) | 0.46759 (14) | 0.0624 (5) | |
| C6 | 0.2561 (3) | 0.38746 (11) | 0.32045 (13) | 0.0394 (4) | |
| C7 | 0.2444 (3) | 0.50366 (11) | 0.37490 (13) | 0.0383 (4) | |
| C8 | 0.9941 (3) | 0.96341 (10) | 0.38748 (13) | 0.0350 (4) | |
| C9 | 0.8136 (3) | 1.00364 (12) | 0.35338 (13) | 0.0420 (4) | |
| H9 | 0.682079 | 0.982192 | 0.350086 | 0.050* | |
| C10 | 0.8389 (3) | 1.07772 (13) | 0.32431 (15) | 0.0490 (5) | |
| H10 | 0.720945 | 1.106402 | 0.300336 | 0.059* | |
| C11 | 1.0345 (4) | 1.11046 (13) | 0.32983 (16) | 0.0531 (5) | |
| H11 | 1.044476 | 1.160508 | 0.310364 | 0.064* | |
| C12 | 1.2147 (3) | 1.06995 (12) | 0.36377 (16) | 0.0483 (5) | |
| H12 | 1.346707 | 1.091225 | 0.368116 | 0.058* | |
| C13 | 1.1870 (3) | 0.99662 (11) | 0.39057 (13) | 0.0377 (4) | |
| C14 | 1.2326 (3) | 0.87935 (11) | 0.44171 (13) | 0.0372 (4) | |
| C15 | 0.6703 (3) | 0.65540 (10) | 0.43310 (13) | 0.0354 (4) | |
| C16 | 0.8301 (3) | 0.72137 (11) | 0.44698 (14) | 0.0379 (4) |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0305 (7) | 0.0392 (7) | 0.0574 (8) | −0.0051 (5) | 0.0037 (5) | −0.0028 (6) |
| N1 | 0.0284 (8) | 0.0363 (9) | 0.0492 (8) | −0.0048 (6) | 0.0058 (6) | −0.0030 (7) |
| C1 | 0.0356 (10) | 0.0348 (10) | 0.0396 (9) | −0.0046 (8) | 0.0071 (7) | 0.0037 (7) |
| O2 | 0.0322 (7) | 0.0382 (7) | 0.0536 (8) | −0.0047 (5) | 0.0098 (5) | 0.0007 (6) |
| N2 | 0.0331 (9) | 0.0404 (10) | 0.0844 (13) | −0.0023 (8) | 0.0144 (9) | −0.0085 (9) |
| C2 | 0.0377 (11) | 0.0428 (11) | 0.0523 (11) | 0.0007 (8) | 0.0110 (8) | 0.0039 (9) |
| O3 | 0.0292 (7) | 0.0391 (8) | 0.0945 (11) | −0.0031 (6) | 0.0131 (7) | −0.0047 (8) |
| N3 | 0.0298 (8) | 0.0342 (9) | 0.0515 (9) | −0.0049 (7) | 0.0101 (6) | −0.0018 (7) |
| C3 | 0.0567 (14) | 0.0396 (11) | 0.0626 (13) | 0.0058 (10) | 0.0202 (10) | 0.0046 (10) |
| O4 | 0.0327 (7) | 0.0323 (7) | 0.0645 (8) | −0.0021 (5) | 0.0086 (6) | −0.0027 (6) |
| N4 | 0.0360 (10) | 0.0392 (10) | 0.0663 (11) | 0.0014 (8) | 0.0102 (8) | 0.0037 (8) |
| C4 | 0.0648 (15) | 0.0344 (11) | 0.0637 (13) | −0.0072 (10) | 0.0199 (11) | −0.0045 (10) |
| O5 | 0.0324 (7) | 0.0332 (7) | 0.0900 (11) | −0.0013 (6) | 0.0120 (7) | 0.0054 (7) |
| C5 | 0.0486 (12) | 0.0430 (12) | 0.0579 (12) | −0.0135 (9) | 0.0105 (9) | −0.0027 (9) |
| O6 | 0.0291 (8) | 0.0397 (9) | 0.1155 (14) | −0.0015 (6) | 0.0047 (8) | 0.0032 (8) |
| C6 | 0.0351 (10) | 0.0378 (10) | 0.0451 (10) | −0.0019 (8) | 0.0063 (7) | 0.0037 (8) |
| C7 | 0.0328 (9) | 0.0344 (10) | 0.0477 (10) | −0.0039 (7) | 0.0066 (7) | 0.0009 (8) |
| C8 | 0.0355 (10) | 0.0337 (10) | 0.0367 (8) | −0.0029 (7) | 0.0093 (7) | −0.0032 (7) |
| C9 | 0.0353 (10) | 0.0433 (11) | 0.0476 (10) | 0.0004 (8) | 0.0082 (8) | −0.0014 (9) |
| C10 | 0.0491 (12) | 0.0459 (12) | 0.0525 (11) | 0.0074 (9) | 0.0102 (9) | 0.0043 (9) |
| C11 | 0.0620 (14) | 0.0383 (12) | 0.0616 (13) | −0.0022 (10) | 0.0180 (10) | 0.0085 (10) |
| C12 | 0.0476 (12) | 0.0418 (12) | 0.0576 (12) | −0.0100 (9) | 0.0154 (9) | 0.0013 (9) |
| C13 | 0.0361 (10) | 0.0357 (10) | 0.0423 (9) | −0.0014 (8) | 0.0098 (7) | −0.0029 (8) |
| C14 | 0.0330 (10) | 0.0340 (10) | 0.0453 (9) | −0.0050 (7) | 0.0090 (7) | −0.0041 (8) |
| C15 | 0.0304 (9) | 0.0343 (10) | 0.0420 (9) | −0.0025 (7) | 0.0079 (7) | 0.0009 (8) |
| C16 | 0.0305 (9) | 0.0336 (10) | 0.0498 (10) | −0.0033 (7) | 0.0077 (7) | 0.0007 (8) |
Geometric parameters (Å, º)
| O1—C6 | 1.397 (2) | N4—H4A | 0.866 (10) |
| O1—C7 | 1.349 (2) | N4—H4B | 0.858 (10) |
| N1—H1 | 0.876 (10) | N4—C14 | 1.303 (3) |
| N1—C1 | 1.400 (3) | C4—H4 | 0.9300 |
| N1—C7 | 1.328 (2) | C4—C5 | 1.390 (3) |
| C1—C2 | 1.374 (3) | O5—C16 | 1.276 (2) |
| C1—C6 | 1.386 (3) | C5—H5 | 0.9300 |
| O2—C13 | 1.400 (2) | C5—C6 | 1.364 (3) |
| O2—C14 | 1.357 (2) | O6—C16 | 1.222 (2) |
| N2—H2A | 0.865 (10) | C8—C9 | 1.382 (3) |
| N2—H2B | 0.857 (10) | C8—C13 | 1.380 (3) |
| N2—C7 | 1.296 (3) | C9—H9 | 0.9300 |
| C2—H2 | 0.9300 | C9—C10 | 1.388 (3) |
| C2—C3 | 1.385 (3) | C10—H10 | 0.9300 |
| O3—C15 | 1.234 (2) | C10—C11 | 1.388 (3) |
| N3—H3A | 0.877 (10) | C11—H11 | 0.9300 |
| N3—C8 | 1.391 (2) | C11—C12 | 1.382 (3) |
| N3—C14 | 1.321 (2) | C12—H12 | 0.9300 |
| C3—H3 | 0.9300 | C12—C13 | 1.369 (3) |
| C3—C4 | 1.392 (3) | C15—C16 | 1.553 (3) |
| O4—C15 | 1.266 (2) | ||
| C7—O1—C6 | 105.93 (14) | C5—C6—C1 | 123.77 (19) |
| C1—N1—H1 | 129 (2) | N1—C7—O1 | 111.77 (16) |
| C7—N1—H1 | 123 (2) | N2—C7—O1 | 120.69 (17) |
| C7—N1—C1 | 107.77 (15) | N2—C7—N1 | 127.53 (18) |
| C2—C1—N1 | 133.15 (18) | C9—C8—N3 | 132.26 (18) |
| C2—C1—C6 | 120.73 (18) | C13—C8—N3 | 107.36 (16) |
| C6—C1—N1 | 106.12 (16) | C13—C8—C9 | 120.37 (18) |
| C14—O2—C13 | 105.31 (14) | C8—C9—H9 | 121.8 |
| H2A—N2—H2B | 122 (3) | C8—C9—C10 | 116.46 (19) |
| C7—N2—H2A | 122.7 (18) | C10—C9—H9 | 121.8 |
| C7—N2—H2B | 115.0 (19) | C9—C10—H10 | 118.9 |
| C1—C2—H2 | 121.8 | C9—C10—C11 | 122.2 (2) |
| C1—C2—C3 | 116.40 (19) | C11—C10—H10 | 118.9 |
| C3—C2—H2 | 121.8 | C10—C11—H11 | 119.4 |
| C8—N3—H3A | 123 (2) | C12—C11—C10 | 121.1 (2) |
| C14—N3—H3A | 129 (2) | C12—C11—H11 | 119.4 |
| C14—N3—C8 | 107.10 (15) | C11—C12—H12 | 122.1 |
| C2—C3—H3 | 118.8 | C13—C12—C11 | 115.9 (2) |
| C2—C3—C4 | 122.3 (2) | C13—C12—H12 | 122.1 |
| C4—C3—H3 | 118.8 | C8—C13—O2 | 107.87 (16) |
| H4A—N4—H4B | 119 (2) | C12—C13—O2 | 128.21 (18) |
| C14—N4—H4A | 120.4 (17) | C12—C13—C8 | 123.92 (19) |
| C14—N4—H4B | 115.1 (18) | N3—C14—O2 | 112.34 (16) |
| C3—C4—H4 | 119.5 | N4—C14—O2 | 119.57 (17) |
| C5—C4—C3 | 120.9 (2) | N4—C14—N3 | 128.08 (18) |
| C5—C4—H4 | 119.5 | O3—C15—O4 | 125.89 (17) |
| C4—C5—H5 | 122.1 | O3—C15—C16 | 117.56 (16) |
| C6—C5—C4 | 115.8 (2) | O4—C15—C16 | 116.55 (16) |
| C6—C5—H5 | 122.1 | O5—C16—C15 | 115.62 (16) |
| C1—C6—O1 | 108.39 (16) | O6—C16—O5 | 125.33 (18) |
| C5—C6—O1 | 127.84 (18) | O6—C16—C15 | 119.06 (17) |
| N1—C1—C2—C3 | −179.9 (2) | C6—C1—C2—C3 | 1.4 (3) |
| N1—C1—C6—O1 | −1.0 (2) | C7—O1—C6—C1 | 0.03 (19) |
| N1—C1—C6—C5 | 178.36 (18) | C7—O1—C6—C5 | −179.3 (2) |
| C1—N1—C7—O1 | −1.8 (2) | C7—N1—C1—C2 | −177.2 (2) |
| C1—N1—C7—N2 | 179.0 (2) | C7—N1—C1—C6 | 1.7 (2) |
| C1—C2—C3—C4 | 0.9 (3) | C8—N3—C14—O2 | 1.1 (2) |
| C2—C1—C6—O1 | 178.00 (16) | C8—N3—C14—N4 | 179.93 (19) |
| C2—C1—C6—C5 | −2.6 (3) | C8—C9—C10—C11 | −0.6 (3) |
| C2—C3—C4—C5 | −2.0 (3) | C9—C8—C13—O2 | −178.45 (16) |
| O3—C15—C16—O5 | −10.1 (3) | C9—C8—C13—C12 | 1.8 (3) |
| O3—C15—C16—O6 | 169.97 (19) | C9—C10—C11—C12 | 0.8 (3) |
| N3—C8—C9—C10 | −179.46 (19) | C10—C11—C12—C13 | 0.3 (3) |
| N3—C8—C13—O2 | 0.65 (19) | C11—C12—C13—O2 | 178.73 (18) |
| N3—C8—C13—C12 | −179.10 (18) | C11—C12—C13—C8 | −1.6 (3) |
| C3—C4—C5—C6 | 0.9 (3) | C13—O2—C14—N3 | −0.71 (19) |
| O4—C15—C16—O5 | 169.79 (17) | C13—O2—C14—N4 | −179.63 (17) |
| O4—C15—C16—O6 | −10.2 (3) | C13—C8—C9—C10 | −0.6 (3) |
| C4—C5—C6—O1 | −179.32 (18) | C14—O2—C13—C8 | 0.00 (18) |
| C4—C5—C6—C1 | 1.4 (3) | C14—O2—C13—C12 | 179.74 (19) |
| C6—O1—C7—N1 | 1.1 (2) | C14—N3—C8—C9 | 177.88 (19) |
| C6—O1—C7—N2 | −179.66 (18) | C14—N3—C8—C13 | −1.07 (19) |
Hydrogen-bond geometry (Å, º)
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1···O4 | 0.88 (1) | 1.78 (1) | 2.650 (2) | 176 (3) |
| N2—H2A···O4i | 0.87 (1) | 2.00 (1) | 2.863 (2) | 174 (3) |
| N2—H2B···O3 | 0.86 (1) | 1.94 (1) | 2.770 (2) | 164 (2) |
| C2—H2···O1ii | 0.93 | 2.65 | 3.522 (2) | 157 |
| N3—H3A···O5 | 0.88 (1) | 1.71 (1) | 2.577 (2) | 173 (3) |
| N4—H4A···O5ii | 0.87 (1) | 2.06 (1) | 2.918 (2) | 172 (2) |
| N4—H4B···O6 | 0.86 (1) | 2.02 (1) | 2.851 (2) | 163 (2) |
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z.
Funding Statement
Funding for this research was provided by: Ministry of Higher Education, Science and Innovation of the Republic of Uzbekistan.
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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/S2414314624000336/bv4051sup1.cif
Supporting information file. DOI: 10.1107/S2414314624000336/bv4051Isup2.cml
CCDC reference: 2324364
Additional supporting information: crystallographic information; 3D view; checkCIF report