research papers\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoSTRUCTURAL
CHEMISTRY
ISSN: 2053-2296

Conversion of 3-amino-4-aryl­amino-1H-iso­chromen-1-ones to 1-aryl­iso­chromeno[3,4-d][1,2,3]triazol-5(1H)-ones: synthesis, spectroscopic characterization and the structures of four products and one ring-opened derivative

aFacultad de Ciencias, Universidad de Ciencias Aplicadas y Ambientales, Calle 222, No. 55-37, Bogotá, Colombia, bDepartamento de Química, Universidad Nacional de Colombia, Cuidad Universitaria, Carrera 30, No. 45-03, Edificio 451, Bogotá, Colombia, cDepartamento de Química Inorgánica y Orgánica, Universidad de Jaén, 23071 Jaén, Spain, and dSchool of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland
*Correspondence e-mail: cg@st-andrews.ac.uk

Edited by A. L. Spek, Utrecht University, The Netherlands (Received 12 March 2020; accepted 13 March 2020; online 20 April 2020)

An efficient synthesis of 1-aryl­isochromeno[3,4-d][1,2,3]triazol-5(1H)-ones, involving the diazo­tization of 3-amino-4-aryl­amino-1H-isochromen-1-ones in weakly acidic solution, has been developed and the spectroscopic characterization and crystal structures of four examples are reported. The mol­ecules of 1-phenyl­isochromeno[3,4-d][1,2,3]triazol-5(1H)-one, C15H9N3O2, (I), are linked into sheets by a combination of C—H⋯N and C—H⋯O hydrogen bonds, while the structures of 1-(2-methyl­phen­yl)isochromeno[3,4-d][1,2,3]triazol-5(1H)-one, C16H11N3O2, (II), and 1-(3-chloro­phen­yl)isochromeno[3,4-d][1,2,3]triazol-5(1H)-one, C15H8ClN3O2, (III), each contain just one hydrogen bond which links the mol­ecules into simple chains, which are further linked into sheets by π-stacking inter­actions in (II) but not in (III). In the structure of 1-(4-chloro­phen­yl)isochromeno[3,4-d][1,2,3]triazol-5(1H)-one, (IV), isomeric with (III), a combination of C—H⋯O and C—H⋯π(arene) hydrogen bonds links the mol­ecules into sheets. When com­pound (II) was exposed to a strong acid in methanol, qu­anti­tative conversion occurred to give the ring-opened transesterification product methyl 2-[4-hy­droxy-1-(2-methyl­phen­yl)-1H-1,2,3-triazol-5-yl]benzoate, C17H15N3O3, (V), where the mol­ecules are linked by paired O—H⋯O hydrogen bonds to form centrosymmetric dimers.

1. Introduction

Isocoumarins are an important building block in synthetic medicinal chemistry because they have shown inter­esting bio­activities, for example, as anti­coagulants (Oweida et al., 1990[Oweida, S. W., Ku, D. N., Lumsden, A. B., Kam, C. M. & Powers, J. C. (1990). Thromb. Res. 58, 191-197.]), as herbicides (Zhang et al., 2016[Zhang, Z., Huo, J. Q., Dong, H. J., Shi, J. M. & Zhang, J. L. (2016). Asian J. Chem. 28, 666-668.]) and as insecticides (Qadeer et al., 2007[Qadeer, G., Rama, N. H., Fan, Z. J., Liu, B. & Liu, X. F. (2007). J. Braz. Chem. Soc. 18, 1176-1182.]). In order to gain access to com­pounds of this type in a straightforward way, a synthetic route has been developed using reactions between 2-formyl­benzoic acid, hydrogen cyanide and anilines to yield N-aryldi­amino­isocoumarins (Opatz & Ferenc, 2005[Opatz, T. & Ferenc, D. (2005). Eur. J. Org. Chem. 2005, 817-821.]). We have reported the structures of several com­pounds of this type (Vicentes et al., 2013[Vicentes, D. E., Rodríguez, R., Cobo, J. & Glidewell, C. (2013). Acta Cryst. C69, 770-773.]) and, more recently using such com­pounds as precursors, we have developed the synthesis of a new heterocyclic system, namely fused imidazolo­isocoumarins, as part of an exploration of possible synergies between the imidazole and isocoumarin pharmacophores (Rodríguez et al., 2017[Rodríguez, R., Vicentes, D. E., Cobo, J. & Nogueras, M. (2017). Tetrahedron Lett. 58, 1487-1489.]).

The bioactivity of hybrid systems containing the 1,2,3-triazole unit has been reviewed recently (Xu et al., 2019[Xu, Z., Zhao, S. J. & Liu, Y. (2019). Eur. J. Med. Chem. 183, 111700.]) and, with this in mind, we have now developed an efficient synthesis of 1-aryl­isochromeno[3,4-d][1,2,3]triazol-5(1H)-ones starting from the same N-aryldi­amino­isocoumarins as were used in the synthesis of imidazolo­isocoumarins (Rodríguez et al., 2017[Rodríguez, R., Vicentes, D. E., Cobo, J. & Nogueras, M. (2017). Tetrahedron Lett. 58, 1487-1489.]). Thus, we now report the synthesis and spectroscopic characterization, and the mol­ecular and supra­molecular structures of four representative examples, namely, 1-phenyl­iso­chro­meno[3,4-d][1,2,3]triazol-5(1H)-one, (I), 1-(2-methyl­phen­yl)isochromeno[3,4-d][1,2,3]triazol-5(1H)-one, (II), 1-(3-chloro­phen­yl)isochromeno[3,4-d][1,2,3]triazol-5(1H)-one, (III), and 1-(4-chloro­phen­yl)isochromeno[3,4-d][1,2,3]triazol-5(1H)-one, (IV), carrying substituents at different positions in the pendent aryl group, along with those of a transesterification product, namely, methyl 2-[4-hy­droxy-1-(2-methyl­phen­yl)-1H-1,2,3-tri­azol-5-yl]benzoate, (V)[link]. Compounds (I)–(IV) were prepared by reaction of sodium nitrite in acetic acid with the corresponding 3-amino-4-aryl­amino-1H-isochromen-1-ones (A) (see Scheme 1); the precursors of type (A) having aryl = phenyl, 2-methyl­phenyl or 4-chloro­phenyl were prepared (Scheme 1) as reported previously (Rodríguez et al., 2017[Rodríguez, R., Vicentes, D. E., Cobo, J. & Nogueras, M. (2017). Tetrahedron Lett. 58, 1487-1489.]), and the new analogue having aryl = 3-chloro­phenyl was prepared in the same way. The conversion of the precursors of type (A) to the products (I)–(IV) proceeds via the diazo­nium inter­mediate (B) (Scheme 1), which itself undergoes an intra­molecular cyclization to form the triazolo ring. It is important to stress here the necessity of using a weak acid, here acetic acid, in the diazo­tization of (A) to form (B), as isocoumarins often readily undergo ring opening in the presence of strong acids. To confirm this, a sample of com­pound (II)[link] was stirred in methanol in the presence of aqueous hydro­chloric acid, resulting in a qu­anti­tative conversion of (II)[link] to ester (V)[link].

2. Experimental

2.1. Synthesis and crystallization

The known precursors of type (A) (see Scheme 1) having Ar = C6H5, 2-CH3C6H4 and 4-ClC6H4 were prepared as described previously (Rodríguez et al., 2017[Rodríguez, R., Vicentes, D. E., Cobo, J. & Nogueras, M. (2017). Tetrahedron Lett. 58, 1487-1489.]); the new ana­logue having Ar = 3-ClC6H4 was prepared following the same procedure. Analytical data for 3-amino-4-(3-chloro­anilino)-1H-iso­chro­men-1-one: yellow solid, yield 71%, m.p. 451–452 K; IR (ATR, cm−1): 3456, 3319, 2922, 1701, 1592, 1474, 1306, 1089, 767, 679; NMR [CDCl3, the numbering of the chloro­phenyl ring follows that for com­pound (III)]: δ(1H) 8.15 (dd, J = 8.0, 0.7 Hz, 1H, H8), 7.53 (t, J = 7.6 Hz, 1H, H6), 7.20 (t, J = 7.6 Hz, 1H, H7), 7.16 (d, J = 8.1 Hz, 1H, H5), 7.10 (t, J = 8.0 Hz, 1H, H15), 6.76 (dd, J = 7.9, 1.1 Hz, 1H, H14), 6.65 (t, J = 2.0 Hz, 1H, H12), 6.56 (dd, J = 8.2, 1.6 Hz, 1H, H16), 4.85 (s, 1H, NH), 4.57 (s, 2H, NH2); δ(13C) 160.64 (CO), 154.78 (C3), 147.59 (C11), 140.40 (C4A), 135.65 (C13), 135.52 (C6), 130.86 (C15), 130.56 (C8), 124.23 (C7), 119.74 (C5), 119.29 (C14), 116.15 (C8A), 113.24 (C12), 111.59 (C16), 92.19 (C4); MS (EI, 70 eV): m/z (%) 285.9 (12) [M]+, 259.94 (31), 257.93 (100), 177.97 (16), 148.92 (20), 129.93 (21), 110.89 (17), 103.92 (17); HRMS (ESI–QTOF) found 287.0582, C15H1135ClN2O2 requires for [M + H]+ 287.0578.

For the synthesis of com­pounds (I)–(IV), sodium nitrite (153 mg, 2.22 mmol) was added to a suspension of the appropriate precursor (A) [1.09 mmol; 275 mg for (I)[link], 290 mg for (II)[link] and 313 mg for each of (III)[link] and (IV)] in acetic acid (1.0 ml) and the resulting mixture was then stirred at ambient temperature for 5 min. The resulting solid precipitate was collected by filtration and washed with an aqueous solution of sodium hydrogen carbonate (10% w/v) and then with water. The crude solid products were purified by column chromatography on silica gel 60 (0.040–0.063 mm) using di­chloro­methane as eluent.

[Scheme 1]

Analytical data for compound (I)[link], colourless solid, yield 77%, m.p. 433–434 K; IR (ATR, cm−1): 3065, 1736, 1622, 1493, 1208, 1019, 763, 715; NMR (CDCl3): δ(1H) 8.46 (dd, J = 7.5, 1.6 Hz, 1H, H6), 7.72–7.55 (m, 7H, H7, H8, H12, H13, H14, H15, H16), 7.29 (dd, J = 7.8, 1.0 Hz, 1H, H9); δ(13C) 160.18 (CO), 154.65 (C3A), 136.89 (C11), 135.41 (C8), 132.84 (C6), 131.24 (C14), 130.23 (C13, C15), 129.79 (C7), 126.27 (C9A), 126.11 (C12, C16), 121.25 (C9), 120.57 (C9B), 115.26 (C5A); MS (EI, 70 eV): m/z (%) 262.98 (2) [M]+, 223.99 (35), 178.98 (100), 178.00 (29), 148.93 (36), 104.94 (23), 76.95 (35); HRMS (ESI–QTOF) found 264.0768, C15H9N3O3 requires for [M + H]+ 264.0768.

Analytical data for compound (II)[link], colourless solid, yield 74%, m.p. 439–440 K; IR (ATR, cm−1): 1745, 1622, 1012, 987, 764, 680; NMR (CDCl3): δ(1H) 8.45 (dd, J = 7.1, 2.2 Hz, 1H, H8), 7.66–7.57 (m, 3H, H6, H7, H13), 7.55–7.48 (m, 2H, H14, H15), 7.46 (dd, J = 7.8, 1.6 Hz, 1H, H16), 6.92 (dd, J = 7.0, 2.1 Hz, 1H, H5), 2.10 (s, 3H, CH3); δ(13C) 160.22 (CO), 154.34 (C3A), 135.85 (C11), 135.69 (C8), 132.67 (C6), 131.89 (C14), 131.66 (C13), 129.78 (C7), 127.73 (C16), 127.38 (C15), 126.19 (C9A), 120.63 (C9), 120.46 (C9B), 115.62 (C5A), 17.32 (CH3); MS (EI, 70 eV): m/z (%) 276,97 (2) [M]+, 220.99 (16), 194.02 (15), 193.00 (100), 192.02 (21), 164.97 (22), 88.94 (22); HRMS (ESI–QTOF) found 278.0923, C16H11N3O2 requires for [M + H]+ 278.0924.

Analytical data for compound (III)[link], yellow solid, yield 75%, m.p. 448–449 K; IR (ATR, cm−1): 3072, 2919, 2850, 1748, 1617, 1587, 1010, 885, 867, 783; NMR (CDCl3): δ(1H) 8.46 (dd, J = 7.9, 1.4 Hz, 1H, H6), 7.75–7.60 (m, 5H, H7, H8, H12, H14, H15), 7.56 (ddd, J = 7.7, 1.9, 1.4 Hz, 1H, H16), 7.34 (dd, J = 7.9, 0.6 Hz, 1H, H9); δ(13C) 159.94 (CO), 154.65 (C3A), 137.75 (C11), 136.03 (C13), 135.57 (C8), 132.95 (C6), 131.47 (C15), 131.22 (C14), 130.04 (C7), 126.46 (C12), 125.92 (C9A), 124.23 (C16), 121.20 (C9), 120.57 (C9B), 115.22 (C5A); MS (EI, 70 eV): m/z (%) 296.95 (2) [M]+, 214.96 (29), 213.98 (15), 212.01 (100), 177.98 (47), 150.97 (15), 74.94 (27); HRMS (ESI–QTOF) found 298.0380, C15H835ClN3O2 requires for [M + H]+ 298.0378.

Analytical data for compound (IV)[link], pink solid, yield 62%,, m.p. 490–492 K; IR (ATR, cm−1): 3087, 3066, 1740, 1620, 1457, 1217, 1013, 832, 764; NMR (CDCl3) δ(1H) 8.46 (ddd, J = 7.8, 1.5, 0.6 Hz, 1H, H6), 7.72–7.58 (m, 6H, H7, H8, H12, H13, H15, H16), 7.32 (ddd, J = 7.9, 1.3, 0.5 Hz, 1H, H9); δ(13C) 159.98 (CO), 154.69 (C3A), 137.45 (C11), 135.51 (C8), 135.30 (C14), 132.96 (C6), 130.53 (C13, C15), 130.00 (C7), 127.39 (C12, C16), 126.02 (C9A), 121.14 (C9), 120.59 (C9B), 115.25 (C5A); MS (EI, 70 eV): m/z (%) 296.93 (1.4) [M]+, 214.95 (31), 213.96 (15), 212.90 (100), 177.97 (39), 150.96 (14), 110.91 (13), 74.93 (25); HRMS (ESI–QTOF) found 298.0379, C15H835ClN3O2 requires for [M + H]+ 298.0378.

For the conversion of com­pound (II)[link] into com­pound (V)[link], a sample of (II)[link] (2.00 g, 7.22 mmol) and aqueous hydro­chloric acid (1 mol dm−3, 1 ml) were added to methanol (9 ml) and the resulting mixture was then stirred for 24 h at ambient temperature. The solvent was removed under reduced pressure and the resulting solid product was washed with an aqueous solution of sodium hydrogen carbonate (10% w/v) and then with water and finally dried in air to provide (V)[link] as a colourless solid in qu­anti­tative yield (m.p. 463–464 K). Ana­lytical data: IR (ATR, cm−1): 2982, 2948, 1722, 1623, 1512, 1259, 764, 713; NMR (CDCl3): δ(1H) 10.48 (s, 1H, OH), 7.76 (d, J = 7.7 Hz, 1H, H3), 7.51 (td, J = 7.5, 1.2 Hz, 1H, H5), 7.44 (t, J = 7.2 Hz, 1H, H4), 7.40–7.29 (m, 2H, H213, H214), 7.26 (td, J = 7.7, 1.1 Hz, 1H, H215), 7.23–7.16 (m, 2H, H6, H216), 3.67 (s, 3H, OCH3), 2.02 (s, 3H, CH3); δ(13C) 166.53 (CO), 155.36 (C24), 135.61 (C211), 134.49 (C214), 131.80 (C5), 131.38 (C6), 131.09 (C213), 130.85 (C25), 129.94 (C3), 129.70 (C214), 128.85 (C4), 127.39 (C216), 126.52 (C215), 126.40 (C1), 119.03 (C2), 52.12 (OCH3), 17.07 (CH3); MS (EI, 70 eV): m/z (%) 309.00 (2) [M]+, 239.01 (16), 237.98 (100), 219.99 (21), 193.00 (70), 164.97 (23), 90.96 (30); HRMS (ESI–QTOF) found 310.1186, C17H15N3O2 requires for [M + H]+ 310.1186.

Crystals of com­pounds (I)–(V) suitable for single-crystal X-ray diffraction were grown by slow evaporation, at ambient temperature and in the presence of air, of solutions in chloro­form.

2.2. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1[link]. All H atoms were located in difference maps. H atoms bonded to C atoms were subsequently treated as riding atoms in geometrically idealized positions, with C—H = 0.95 (alkenyl and aromatic) or 0.98 Å (CH3) and with Uiso(H) = kUeq(C), where k = 1.5 for the methyl groups, which were allowed to rotate but not to tilt, and 1.2 for all other H atoms bonded to C atoms. For the H atom bonded to an O atom in com­pound (V)[link], the atomic coordinates were refined with Uiso(H) = 1.5Ueq(O), giving an O—H distance of 0.90 (2) Å. Several low-angle reflections which had been attenuated by the beam stop were omitted, i.e. [\overline{1}]01 for (II)[link] and [\overline{1}]02 for (IV)[link]; in addition, one bad outlier reflection, i.e. [\overline{6}]06, was omitted from the data set for (II)[link] before the final refinements. For several of the refinements, the final analyses of variance showed unexpected values of K = [mean(Fo2)/mean(Fc2)] for the groups of the very weakest reflections. Thus, for (III)[link] and (IV)[link], respectively, −0.035 and −0.125 for 312 and 289 reflections in the Fc/Fc(max) ranges 0.000–0.008 and 0.000–0.010, and for (V)[link], 3.550 for 339 reflections in the Fc/Fc(max) range 0.000–0.009; these values are probably statistical artefacts.

Table 1
Experimental details

For all structures: Z = 4. Experiments were carried out at 100 K with Mo Kα radiation using a Bruker D8 Venture diffractometer. Absorption was corrected for by multi-scan methods (SADABS; Bruker, 2016[Bruker (2016). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]).

  (I) (II) (III)
Crystal data
Chemical formula C15H9N3O2 C16H11N3O2 C15H8ClN3O2
Mr 263.25 277.28 297.69
Crystal system, space group Monoclinic, P21/n Monoclinic, P21/n Monoclinic, P21/c
a, b, c (Å) 11.6814 (5), 6.4310 (3), 16.0589 (8) 7.5676 (5), 20.2663 (14), 9.2503 (7) 11.0993 (8), 12.8996 (9), 9.2234 (6)
β (°) 100.687 (2) 112.957 (3) 106.675 (2)
V3) 1185.47 (10) 1306.33 (16) 1265.04 (15)
μ (mm−1) 0.10 0.10 0.31
Crystal size (mm) 0.20 × 0.12 × 0.06 0.28 × 0.17 × 0.16 0.20 × 0.12 × 0.05
 
Data collection
Tmin, Tmax 0.936, 0.994 0.941, 0.985 0.895, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections 26237, 2747, 2400 36209, 3242, 2915 28194, 2905, 2495
Rint 0.037 0.034 0.044
(sin θ/λ)max−1) 0.652 0.668 0.650
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.103, 1.04 0.036, 0.098, 1.05 0.032, 0.089, 1.08
No. of reflections 2747 3242 2905
No. of parameters 181 191 190
H-atom treatment H-atom parameters constrained H-atom parameters constrained H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.31, −0.21 0.31, −0.25 0.32, −0.36
  (IV) (V)
Crystal data
Chemical formula C15H8ClN3O2 C17H15N3O3
Mr 297.69 309.32
Crystal system, space group Monoclinic, P21/c Monoclinic, P21/c
a, b, c (Å) 16.7331 (12), 5.9676 (4), 13.681 (1) 11.1518 (5), 9.3143 (4), 14.2417 (6)
β (°) 112.820 (3) 98.655 (2)
V3) 1259.21 (16) 1462.46 (11)
μ (mm−1) 0.31 0.10
Crystal size (mm) 0.25 × 0.14 × 0.11 0.19 × 0.11 × 0.07
 
Data collection
Tmin, Tmax 0.880, 0.967 0.960, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections 34775, 2891, 2413 33834, 3360, 3084
Rint 0.056 0.036
(sin θ/λ)max−1) 0.650 0.650
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.087, 1.12 0.042, 0.098, 1.07
No. of reflections 2891 3360
No. of parameters 190 213
H-atom treatment H-atom parameters constrained H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 0.37, −0.26 0.34, −0.22
Computer programs: APEX3 (Bruker, 2018[Bruker (2018). APEX3 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]), SAINT (Bruker, 2018[Bruker (2018). APEX3 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXT2014 (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL2014 (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]) and PLATON (Spek, 2020[Spek, A. L. (2020). Acta Cryst. E76, 1-11.]).

3. Results and discussion

The constitutions of com­pounds (I)–(V) were all fully established by a combination of high-resolution mass spectrometry (HRMS), IR spectrosopy and 1H and 13C NMR spectroscopy, further confirmed by the structure analyses reported here (Figs. 1[link]–5[link][link][link][link]). The HRMS data for (I)–(IV) demonstrate the incorporation of an additional H atom, the IR data show the absence of an NH2 absorption around 3400 cm−1 and the 1H NMR spectra show the absence of signals around δ 4.5–5.0 arising from an amino group; these observations taken together confirm the conversion of the di­amino precursors of type (A) (Scheme 1[link]) into the triazolo products (I)–(IV), whose constitutions were fully confirmed by the detailed assignments of the 1H and 13C NMR spectra (see §2.1[link]). Hence, the constitutions of (I)–(IV) show clearly that the anti­cipated triazolo ring formation has occurred, with the additional N atom arising from the diazo­tization process; similarly, the con­stitution of (V)[link] confirms the occurrence of a ring-opening transesterification process.

[Figure 1]
Figure 1
The mol­ecular structure of com­pound (I)[link], showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2]
Figure 2
The mol­ecular structure of com­pound (II)[link], showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 3]
Figure 3
The mol­ecular structure of com­pound (III)[link], showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 4]
Figure 4
The mol­ecular structure of com­pound (IV)[link], showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 5]
Figure 5
The mol­ecular structure of com­pound (V)[link], showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.

Aside from the orientation of the 2-methyl and 3-chloro substituents in com­pounds (II)[link] and (III)[link], respectively, the conformations of com­pounds (I)–(IV) are fairly similar; the dihedral angles between the triazolo ring and the pendent ring (C11–C16) are 65.32 (5), 64.59 (4), 45.48 (8) and 52.32 (9)° in (I)–(IV), respectively. The mol­ecules thus exhibit no inter­nal symmetry and so are conformationally chiral in the crystalline state; the centrosymmetric space groups (Table 1[link]) confirm that (I)–(IV) have all crystallized as conformational racemates. For all of (I)–(IV), the reference mol­ecules were selected to have the same sign for the torsion angle N2—N1—C11—C12, or N2—N1—C11—C16 in the case of (III)[link]. A comparison of the conformation of ester (V)[link] with that of its precursor (II)[link] (Figs. 2[link] and 5[link]) indicates that, in the crystalline state, there appear to have been rotations about both the bonds exocyclic to the triazolo ring in (V)[link], along with a rotation about the bond linking the ester unit to the adjacent aryl ring. The significance of these differences is unclear. The bond lengths in (I)–(V) show no unusual features.

The supra­molecular assembly in com­pounds (I)–(IV) is dominated by contacts of C—H⋯N, C—H⋯O and C—H⋯π(arene) types (Table 2[link]) and it is therefore worthwhile to specify the criteria under which such inter­actions are regarded here is structurally significant, or otherwise. Firstly, we discount all C—H⋯N and C—H⋯O contacts in which the D—H⋯A angle is less than 140°, as the inter­action energies associated with such contacts are likely to be extremely small (Wood et al., 2009[Wood, P. A., Allen, F. H. & Pidcock, E. (2009). CrystEngComm, 11, 1563-1571.]). Secondly, we discount all contacts involving methyl C—H bonds; these are not only of low acidity, but methyl groups CH3E are generally undergoing very fast rotation about the C—E bonds, even in the solid state (Riddell & Rogerson, 1996[Riddell, F. G. & Rogerson, M. (1996). J. Chem. Soc. Perkin Trans. 2, pp. 493-504.], 1997[Riddell, F. G. & Rogerson, M. (1997). J. Chem. Soc. Perkin Trans. 2, pp. 249-256.]). In particular, for methyl groups bonded to aryl rings, as found in (II)[link] and (V)[link], the rotation of the methyl group relative to the ring is subject to a sixfold rotation barrier, known to be in general extremely low, typically just a few J mol−1 rather than the more typical magnitude of a few kJ mol−1 (Tannenbaum et al., 1956[Tannenbaum, E., Myers, R. J. & Gwinn, W. D. (1956). J. Chem. Phys. 25, 42-47.]; Naylor & Wilson, 1957[Naylor, R. E. & Wilson, E. B. (1957). J. Chem. Phys. 26, 1057-1060.]). Hence, there is just one significant inter­molecular C—H⋯X inter­action in each of (II)[link], (III)[link] and (V)[link], involving atoms C13, C16 and O24, respectively, as the donors, and two each in (I)[link] and (IV)[link], involving as the donors C8 and C12 in (I)[link], and C7 and C8 in (IV)[link].

Table 2
Hydrogen bonds and short inter­molecular contacts (Å, °) for com­pounds (I)–(V)

Cg1 and Cg2 represent the centroids of the C5A/C6–C9/C9A and C1–C6 rings, respectively.

Compound D—H⋯A D—H H⋯A DA D—H⋯A
(I) C8—H8⋯N3i 0.95 2.52 3.4641 (16) 173
  C12—H12⋯O5ii 0.95 2.50 3.4136 (16) 161
(II) C7—H7⋯N3iii 0.95 2.55 3.2770 (15) 133
  C13—H13⋯O5iv 0.95 2.54 3.4083 (16) 151
  C15—H15⋯O5v 0.95 2.48 3.2482 (16) 138
(III) C8—H8⋯N3vi 0.95 2.58 3.2465 (19) 127
  C16—H16⋯N2vii 0.95 2.56 3.500 (2) 169
(IV) C6—H6⋯O5viii 0.95 2.53 3.287 (3) 137
  C8—H8⋯O5ix 0.95 2.57 3.578 (2) 161
  C15—H15⋯N3x 0.95 2.52 3.271 (2) 136
  C7—H7⋯Cg1xi 0.95 2.69 3.517 (2) 146
(V) O24—H24⋯N23xii 0.90 (2) 1.77 (2) 2.6721 (15) 177.5 (19)
  C8—H8ACg2xiii 0.98 2.90 3.6605 (16) 135
  C8—H8BCg2viii 0.98 2.90 3.5007 (16) 120
  C8—H8C⋯O24viii 0.98 2.59 3.4004 (19) 140
  C215—H215⋯O24xiv 0.95 2.57 3.2972 (19) 134
Symmetry codes: (i) x + [{1\over 2}], −y + [{1\over 2}], z + [{1\over 2}]; (ii) −x + [{1\over 2}], y + [{1\over 2}], −z + [{1\over 2}]; (iii) x − 1, y, z − 1; (iv) −x + [{1\over 2}], y − [{1\over 2}], −z + [{3\over 2}]; (v) −x + [{3\over 2}], y − [{1\over 2}], −z + [{3\over 2}]; (vi) x, y, z + 1; (vii) x, −y + [{1\over 2}], z + [{1\over 2}]; (viii) −x, −y + 1, −z + 1; (ix) x, −y + [{1\over 2}], z − [{1\over 2}]; (x) x, −y + [{5\over 2}], z − [{1\over 2}]; (xi) −x, y − [{1\over 2}], −z + [{1\over 2}]; (xii) −x + 1, −y + 1, −z + 1; (xiii) −x, y − [{1\over 2}], −z + [{3\over 2}]; (xiv) x, −y + [{3\over 2}], z + [{1\over 2}].

The supra­molecular assembly in com­pound (I)[link] is mediated by two hydrogen bonds, one each of the C—H⋯N and C—H⋯O types (Table 2[link]). Mol­ecules which are related by an n-glide plane are linked by the C—H⋯N hydrogen bond to form a C(7) (Etter, 1990[Etter, M. C. (1990). Acc. Chem. Res. 23, 120-126.]; Etter et al., 1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]; Bernstein et al., 1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]) chain running parallel to the [101] direction, while mol­ecules which are related by a 21 screw axis are linked by a C—H⋯O hydrogen bond to form a C(9) chain running parallel to the [010] direction. The combination of these two chain motifs generates a sheet lying parallel to (10[\overline{1}]) and built of R44(28) rings (Fig. 6[link]).

[Figure 6]
Figure 6
Part of the crystal structure of com­pound (I)[link], showing the formation of a hydrogen-bonded sheet of R44(28) rings parallel to (10[\overline{1}]). Hydrogen bonds are drawn as dashed lines and, for the sake of clarity, H atoms not involved in the motifs shown have been omitted.

For com­pound (II)[link], a single C—H⋯O hydrogen bond links mol­ecules which are related by a 21 screw axis to form a C(10) chain running parallel to the [010] direction (Fig. 7[link]), and chains of this type are linked by two ππ stacking inter­actions, both involving the fused carbocyclic ring, which together generate a π-stacked chain running parallel to [100] (Fig. 8[link]). The combination of these two motifs generates a sheet lying parallel to (001). There is again just one hydrogen bond in the structure of com­pound (III)[link], this time of the C—H⋯N type, linking mol­ecules which are related by a c-glide plane to form a C(5) chain running parallel to the [001] direction (Fig. 9[link]), but here there are no direction-specific inter­actions between adjacent chains.

[Figure 7]
Figure 7
Part of the crystal structure of com­pound (II)[link], showing the formation of a hydrogen-bonded C(10) chain parallel to [010]. Hydrogen bonds are drawn as dashed lines and, for the sake of clarity, H atoms not involved in the motifs shown have been omitted.
[Figure 8]
Figure 8
Part of the crystal structure of com­pound (II)[link], showing the formation of a π-stacked chain parallel to [100]. For the sake of clarity, H atoms have all been omitted. O atoms marked with an asterisk (*), a hash (#), a dollar sign ($) or an ampersand (&) are at the symmetry positions (−x + 1, −y + 1, −z + 1), (−x, −y + 1, −z + 1), (x + 1, y, z) and (x − 1, y, z), respectively.
[Figure 9]
Figure 9
Part of the crystal structure of com­pound (III)[link], showing the formation of a hydrogen-bonded C(5) chain parallel to [001]. Hydrogen bonds are drawn as dashed lines and, for the sake of clarity, H atoms not involved in the motif shown have been omitted.

The assembly in com­pound (IV)[link] is built from a combination of C—H⋯O and C—H⋯π(arene) hydrogen bonds (Table 2[link]). The C—H⋯O hydrogen bond links mol­ecules which are related by a c-glide plane to form a C(7) chain running parallel to the [001] direction (Fig. 10[link]). By contrast, mol­ecules which are related by a 21 screw axis are linked by the C—H⋯π(arene) hydrogen bond to form a chain running parallel to the [010] direction (Fig. 11[link]), and the combination of these two chain motifs generates a sheet lying parallel to (100).

[Figure 10]
Figure 10
Part of the crystal structure of com­pound (IV)[link], showing the formation of a hydrogen-bonded C(7) chain parallel to [001]. Hydrogen bonds are drawn as dashed lines and, for the sake of clarity, H atoms not involved in the motif shown have been omitted.
[Figure 11]
Figure 11
Part of the crystal structure of com­pound (IV)[link], showing the formation of a hydrogen-bonded chain parallel to [010]. Hydrogen bonds are drawn as dashed lines and, for the sake of clarity, H atoms not involved in the motif shown have been omitted.

Paired O—H⋯O hydrogen bonds link inversion-related pairs of mol­ecules of (V)[link] to form a cyclic centrosymmetric R22(8) dimer (Fig. 12[link]), but there are no direction-specific inter­actions between adjacent dimer units.

[Figure 12]
Figure 12
Part of the crystal structure of com­pound (V)[link], showing the formation of a centrosymmetric R22(8) dimer. Hydrogen bonds are drawn as dashed lines and, for the sake of clarity, H atoms bonded to C atoms have all been omitted. Atoms marked with an asterisk (*) are at the symmetry position (−x + 1, −y + 1, −z + 1).

Thus, minor variations in the substituent on the pendent aryl ring in com­pounds (I)–(IV) are associated with significant changes in the pattern of supra­molecular assembly. Whereas for the unsubstituted parent com­pound (I)[link], the mol­ecules are linked into hydrogen-bonded sheets by a combination of C—H⋯N and C—H⋯O hydrogen bonds, the sheet formation in 4-chloro derivative (IV)[link] is based on a combination of C—H⋯O and C—H⋯π(arene) hydrogen bonds. In each of the methyl com­pound (II)[link] and the 3-chloro com­pound (III)[link], a single hydrogen bond, of the C—H⋯O and C—H⋯N types, respectively, links the mol­ecules into simple chains; these chains form π-stacked sheets in (II)[link], but not in (III)[link].

In summary, therefore, we have developed a simple and efficient route to new 1-aryl­isochromeno[3,4-d][1,2,3]triazol-5(1H)-ones, with full spectroscopic and structural characterization of four examples, which show that small changes in substituents are associated with substantial changes in the patterns of supra­molecular aggregation, and we have demonstrated the necessity of using only a weak acid in the synthesis, along with the spectroscopic and structural characterization of a ring-opened derivative.

Supporting information


Computing details top

For all structures, data collection: APEX3 (Bruker, 2018); cell refinement: APEX3 (Bruker, 2018); data reduction: APEX3 (Bruker, 2018); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2020); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b) and PLATON (Spek, 2020).

1-Phenylisochromeno[3,4-d][1,2,3]triazol-5(1H)-one (I) top
Crystal data top
C15H9N3O2F(000) = 544
Mr = 263.25Dx = 1.475 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 11.6814 (5) ÅCell parameters from 2747 reflections
b = 6.4310 (3) Åθ = 2.6–27.6°
c = 16.0589 (8) ŵ = 0.10 mm1
β = 100.687 (2)°T = 100 K
V = 1185.47 (10) Å3Plate, colourless
Z = 40.20 × 0.12 × 0.06 mm
Data collection top
Bruker D8 Venture
diffractometer
2747 independent reflections
Radiation source: INCOATEC high brilliance microfocus sealed tube2400 reflections with I > 2σ(I)
Multilayer mirror monochromatorRint = 0.037
φ and ω scansθmax = 27.6°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
h = 1515
Tmin = 0.936, Tmax = 0.994k = 88
26237 measured reflectionsl = 2020
Refinement top
Refinement on F2Primary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036H-atom parameters constrained
wR(F2) = 0.103 w = 1/[σ2(Fo2) + (0.0472P)2 + 0.6009P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
2747 reflectionsΔρmax = 0.31 e Å3
181 parametersΔρmin = 0.21 e Å3
0 restraints
Special details top

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 (Å2) top
xyzUiso*/Ueq
N10.42457 (8)0.29285 (15)0.11368 (6)0.0179 (2)
N20.35944 (9)0.28467 (17)0.03458 (6)0.0220 (2)
N30.24822 (9)0.28866 (16)0.04153 (7)0.0215 (2)
C3A0.24551 (10)0.29942 (17)0.12447 (8)0.0173 (2)
O40.14429 (7)0.30258 (13)0.15478 (5)0.0192 (2)
C50.15189 (10)0.30615 (17)0.24186 (8)0.0181 (2)
O50.06155 (7)0.31098 (14)0.26774 (6)0.0235 (2)
C5A0.26924 (10)0.30227 (17)0.29667 (7)0.0164 (2)
C60.27436 (10)0.29619 (18)0.38439 (8)0.0195 (2)
H60.20460.29870.40680.023*
C70.38124 (11)0.28646 (19)0.43835 (8)0.0216 (3)
H70.38470.28090.49790.026*
C80.48402 (10)0.28471 (19)0.40587 (7)0.0205 (3)
H80.55700.27750.44350.025*
C90.48066 (10)0.29343 (17)0.31931 (7)0.0178 (2)
H90.55110.29390.29770.021*
C9A0.37320 (10)0.30147 (16)0.26375 (7)0.0153 (2)
C9B0.35513 (9)0.30231 (17)0.17263 (7)0.0159 (2)
C110.54952 (10)0.28664 (19)0.12449 (7)0.0189 (2)
C120.61353 (11)0.4585 (2)0.15790 (8)0.0247 (3)
H120.57580.58030.17260.030*
C130.73450 (11)0.4484 (2)0.16938 (8)0.0282 (3)
H130.78010.56360.19310.034*
C140.78884 (11)0.2714 (2)0.14647 (8)0.0284 (3)
H140.87140.26580.15440.034*
C150.72280 (11)0.1026 (2)0.11200 (8)0.0275 (3)
H150.76040.01760.09560.033*
C160.60190 (10)0.1080 (2)0.10133 (7)0.0224 (3)
H160.55630.00820.07870.027*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0164 (5)0.0208 (5)0.0157 (5)0.0001 (4)0.0010 (4)0.0015 (4)
N20.0204 (5)0.0266 (5)0.0173 (5)0.0001 (4)0.0013 (4)0.0024 (4)
N30.0191 (5)0.0229 (5)0.0206 (5)0.0002 (4)0.0010 (4)0.0012 (4)
C3A0.0147 (5)0.0141 (5)0.0220 (6)0.0002 (4)0.0002 (4)0.0006 (4)
O40.0124 (4)0.0196 (4)0.0243 (4)0.0004 (3)0.0002 (3)0.0002 (3)
C50.0154 (5)0.0121 (5)0.0262 (6)0.0008 (4)0.0026 (4)0.0001 (4)
O50.0146 (4)0.0224 (4)0.0341 (5)0.0003 (3)0.0064 (3)0.0015 (4)
C5A0.0147 (5)0.0124 (5)0.0219 (6)0.0005 (4)0.0025 (4)0.0004 (4)
C60.0193 (5)0.0164 (5)0.0239 (6)0.0006 (4)0.0070 (4)0.0006 (4)
C70.0255 (6)0.0212 (6)0.0181 (5)0.0013 (5)0.0044 (5)0.0007 (4)
C80.0180 (5)0.0218 (6)0.0198 (6)0.0008 (4)0.0014 (4)0.0014 (4)
C90.0142 (5)0.0181 (5)0.0205 (6)0.0000 (4)0.0019 (4)0.0006 (4)
C9A0.0148 (5)0.0118 (5)0.0186 (5)0.0000 (4)0.0016 (4)0.0009 (4)
C9B0.0141 (5)0.0135 (5)0.0195 (6)0.0002 (4)0.0017 (4)0.0006 (4)
C110.0155 (5)0.0265 (6)0.0148 (5)0.0001 (4)0.0030 (4)0.0008 (4)
C120.0228 (6)0.0272 (6)0.0254 (6)0.0039 (5)0.0077 (5)0.0034 (5)
C130.0227 (6)0.0389 (7)0.0241 (6)0.0102 (5)0.0066 (5)0.0043 (5)
C140.0168 (6)0.0504 (8)0.0182 (6)0.0018 (5)0.0042 (4)0.0009 (5)
C150.0215 (6)0.0400 (8)0.0208 (6)0.0069 (5)0.0035 (5)0.0037 (5)
C160.0202 (6)0.0285 (6)0.0177 (5)0.0017 (5)0.0013 (4)0.0028 (5)
Geometric parameters (Å, º) top
N1—N21.3552 (14)C8—C91.3845 (16)
N1—C9B1.3574 (15)C8—H80.9500
N1—C111.4381 (14)C9—C9A1.3997 (15)
N2—N31.3247 (15)C9—H90.9500
N3—C3A1.3398 (15)C9A—C9B1.4392 (15)
C3A—O41.3598 (14)C11—C161.3844 (17)
C3A—C9B1.3678 (15)C11—C121.3855 (17)
O4—C51.3848 (15)C12—C131.3923 (17)
C5—O51.2042 (14)C12—H120.9500
C5—C5A1.4856 (15)C13—C141.386 (2)
C5A—C61.3993 (16)C13—H130.9500
C5A—C9A1.4116 (15)C14—C151.387 (2)
C6—C71.3829 (17)C14—H140.9500
C6—H60.9500C15—C161.3912 (16)
C7—C81.3949 (17)C15—H150.9500
C7—H70.9500C16—H160.9500
N2—N1—C9B110.56 (9)C9A—C9—H9120.1
N2—N1—C11119.53 (10)C9—C9A—C5A119.57 (11)
C9B—N1—C11129.89 (10)C9—C9A—C9B126.40 (10)
N3—N2—N1108.01 (9)C5A—C9A—C9B114.00 (10)
N2—N3—C3A106.80 (10)N1—C9B—C3A102.88 (10)
N3—C3A—O4122.62 (10)N1—C9B—C9A135.65 (10)
N3—C3A—C9B111.75 (10)C3A—C9B—C9A121.35 (10)
O4—C3A—C9B125.62 (11)C16—C11—C12122.15 (11)
C3A—O4—C5117.69 (9)C16—C11—N1118.68 (11)
O5—C5—O4116.93 (10)C12—C11—N1119.17 (11)
O5—C5—C5A124.56 (11)C11—C12—C13118.40 (12)
O4—C5—C5A118.51 (10)C11—C12—H12120.8
C6—C5A—C9A119.85 (10)C13—C12—H12120.8
C6—C5A—C5117.35 (10)C14—C13—C12120.46 (12)
C9A—C5A—C5122.79 (11)C14—C13—H13119.8
C7—C6—C5A119.81 (11)C12—C13—H13119.8
C7—C6—H6120.1C13—C14—C15120.06 (12)
C5A—C6—H6120.1C13—C14—H14120.0
C6—C7—C8120.38 (11)C15—C14—H14120.0
C6—C7—H7119.8C14—C15—C16120.42 (12)
C8—C7—H7119.8C14—C15—H15119.8
C9—C8—C7120.60 (11)C16—C15—H15119.8
C9—C8—H8119.7C11—C16—C15118.50 (12)
C7—C8—H8119.7C11—C16—H16120.8
C8—C9—C9A119.78 (11)C15—C16—H16120.8
C8—C9—H9120.1
C9B—N1—N2—N30.02 (13)N2—N1—C9B—C3A0.02 (12)
C11—N1—N2—N3178.80 (10)C11—N1—C9B—C3A178.69 (11)
N1—N2—N3—C3A0.06 (13)N2—N1—C9B—C9A175.65 (12)
N2—N3—C3A—O4178.86 (10)C11—N1—C9B—C9A3.0 (2)
N2—N3—C3A—C9B0.08 (13)N3—C3A—C9B—N10.06 (13)
N3—C3A—O4—C5177.66 (10)O4—C3A—C9B—N1178.80 (10)
C9B—C3A—O4—C50.95 (16)N3—C3A—C9B—C9A176.40 (10)
C3A—O4—C5—O5179.30 (10)O4—C3A—C9B—C9A2.34 (17)
C3A—O4—C5—C5A1.14 (14)C9—C9A—C9B—N11.4 (2)
O5—C5—C5A—C62.43 (17)C5A—C9A—C9B—N1176.43 (12)
O4—C5—C5A—C6177.09 (10)C9—C9A—C9B—C3A176.48 (11)
O5—C5—C5A—C9A178.50 (11)C5A—C9A—C9B—C3A1.36 (15)
O4—C5—C5A—C9A1.98 (15)N2—N1—C11—C1665.11 (15)
C9A—C5A—C6—C70.91 (16)C9B—N1—C11—C16113.45 (13)
C5—C5A—C6—C7178.19 (10)N2—N1—C11—C12115.11 (13)
C5A—C6—C7—C80.62 (17)C9B—N1—C11—C1266.33 (16)
C6—C7—C8—C90.24 (18)C16—C11—C12—C130.94 (18)
C7—C8—C9—C9A0.80 (17)N1—C11—C12—C13178.83 (11)
C8—C9—C9A—C5A0.50 (16)C11—C12—C13—C141.08 (19)
C8—C9—C9A—C9B177.24 (11)C12—C13—C14—C150.2 (2)
C6—C5A—C9A—C90.35 (16)C13—C14—C15—C161.0 (2)
C5—C5A—C9A—C9178.69 (10)C12—C11—C16—C150.15 (18)
C6—C5A—C9A—C9B178.36 (10)N1—C11—C16—C15179.92 (11)
C5—C5A—C9A—C9B0.69 (15)C14—C15—C16—C111.11 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8···N3i0.952.523.4641 (16)173
C12—H12···O5ii0.952.503.4136 (16)161
Symmetry codes: (i) x+1/2, y+1/2, z+1/2; (ii) x+1/2, y+1/2, z+1/2.
1-(2-Methylphenyl)isochromeno[3,4-d][1,2,3]triazol-5(1H)-one (II) top
Crystal data top
C16H11N3O2F(000) = 576
Mr = 277.28Dx = 1.410 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 7.5676 (5) ÅCell parameters from 3244 reflections
b = 20.2663 (14) Åθ = 2.6–28.3°
c = 9.2503 (7) ŵ = 0.10 mm1
β = 112.957 (3)°T = 100 K
V = 1306.33 (16) Å3Block, colourless
Z = 40.28 × 0.17 × 0.16 mm
Data collection top
Bruker D8 Venture
diffractometer
3242 independent reflections
Radiation source: INCOATEC high brilliance microfocus sealed tube2915 reflections with I > 2σ(I)
Multilayer mirror monochromatorRint = 0.034
φ and ω scansθmax = 28.3°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
h = 910
Tmin = 0.941, Tmax = 0.985k = 2627
36209 measured reflectionsl = 1212
Refinement top
Refinement on F2Primary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036H-atom parameters constrained
wR(F2) = 0.098 w = 1/[σ2(Fo2) + (0.0447P)2 + 0.6412P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
3242 reflectionsΔρmax = 0.31 e Å3
191 parametersΔρmin = 0.25 e Å3
0 restraints
Special details top

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 (Å2) top
xyzUiso*/Ueq
N10.64617 (13)0.39965 (4)0.84757 (10)0.01530 (19)
N20.78444 (13)0.41415 (5)0.99005 (11)0.0188 (2)
N30.77052 (14)0.47755 (5)1.01796 (11)0.0193 (2)
C3A0.62518 (15)0.50189 (5)0.89301 (12)0.0159 (2)
O40.57303 (11)0.56642 (4)0.88252 (9)0.01773 (17)
C50.41921 (15)0.58629 (5)0.74851 (12)0.0162 (2)
O50.37021 (12)0.64284 (4)0.74350 (10)0.02200 (19)
C5A0.33179 (15)0.53730 (5)0.62166 (12)0.0149 (2)
C60.18714 (15)0.56044 (5)0.48412 (13)0.0175 (2)
H60.14720.60520.47690.021*
C70.10215 (16)0.51836 (6)0.35852 (13)0.0190 (2)
H70.00440.53420.26480.023*
C80.15996 (15)0.45252 (6)0.36942 (12)0.0183 (2)
H80.10040.42380.28280.022*
C90.30339 (15)0.42840 (5)0.50514 (12)0.0165 (2)
H90.34220.38360.51100.020*
C9A0.39036 (14)0.47069 (5)0.63331 (12)0.0141 (2)
C9B0.54239 (14)0.45455 (5)0.78150 (12)0.0141 (2)
C110.63623 (15)0.33424 (5)0.78533 (12)0.0157 (2)
C120.47496 (16)0.29469 (5)0.75875 (13)0.0181 (2)
C130.47388 (17)0.23249 (6)0.69298 (14)0.0215 (2)
H130.36600.20440.67140.026*
C140.62740 (18)0.21092 (6)0.65863 (14)0.0227 (2)
H140.62190.16880.61190.027*
C150.78913 (17)0.25035 (6)0.69194 (14)0.0215 (2)
H150.89540.23490.67130.026*
C160.79318 (15)0.31249 (5)0.75567 (13)0.0181 (2)
H160.90240.34000.77890.022*
C170.30969 (17)0.31669 (6)0.79939 (15)0.0243 (2)
H17A0.24310.27790.81670.036*
H17B0.22010.34290.71280.036*
H17C0.35840.34350.89510.036*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0137 (4)0.0163 (4)0.0143 (4)0.0003 (3)0.0038 (3)0.0002 (3)
N20.0166 (4)0.0208 (5)0.0156 (4)0.0009 (3)0.0025 (3)0.0004 (3)
N30.0184 (4)0.0203 (5)0.0162 (4)0.0009 (3)0.0035 (4)0.0010 (3)
C3A0.0154 (5)0.0170 (5)0.0151 (5)0.0016 (4)0.0059 (4)0.0013 (4)
O40.0192 (4)0.0152 (4)0.0164 (4)0.0013 (3)0.0042 (3)0.0028 (3)
C50.0160 (5)0.0168 (5)0.0169 (5)0.0017 (4)0.0076 (4)0.0005 (4)
O50.0246 (4)0.0157 (4)0.0257 (4)0.0003 (3)0.0099 (3)0.0012 (3)
C5A0.0140 (5)0.0165 (5)0.0149 (5)0.0019 (4)0.0066 (4)0.0002 (4)
C60.0167 (5)0.0179 (5)0.0177 (5)0.0002 (4)0.0064 (4)0.0031 (4)
C70.0157 (5)0.0241 (5)0.0155 (5)0.0011 (4)0.0043 (4)0.0032 (4)
C80.0171 (5)0.0228 (5)0.0143 (5)0.0046 (4)0.0053 (4)0.0025 (4)
C90.0164 (5)0.0172 (5)0.0160 (5)0.0017 (4)0.0064 (4)0.0016 (4)
C9A0.0125 (4)0.0166 (5)0.0138 (5)0.0017 (4)0.0059 (4)0.0001 (4)
C9B0.0134 (5)0.0149 (4)0.0143 (5)0.0009 (4)0.0056 (4)0.0003 (4)
C110.0172 (5)0.0140 (5)0.0144 (5)0.0005 (4)0.0045 (4)0.0012 (4)
C120.0185 (5)0.0179 (5)0.0182 (5)0.0010 (4)0.0075 (4)0.0007 (4)
C130.0231 (5)0.0179 (5)0.0232 (5)0.0043 (4)0.0087 (4)0.0011 (4)
C140.0290 (6)0.0157 (5)0.0229 (5)0.0013 (4)0.0098 (5)0.0007 (4)
C150.0216 (5)0.0205 (5)0.0234 (5)0.0045 (4)0.0099 (4)0.0016 (4)
C160.0160 (5)0.0185 (5)0.0186 (5)0.0009 (4)0.0055 (4)0.0025 (4)
C170.0224 (6)0.0235 (6)0.0318 (6)0.0046 (4)0.0157 (5)0.0039 (5)
Geometric parameters (Å, º) top
N1—N21.3574 (12)C9—C9A1.4016 (14)
N1—C9B1.3616 (13)C9—H90.9500
N1—C111.4353 (13)C9A—C9B1.4421 (14)
N2—N31.3229 (13)C11—C161.3909 (15)
N3—C3A1.3406 (14)C11—C121.3994 (15)
C3A—O41.3586 (13)C12—C131.3982 (15)
C3A—C9B1.3686 (14)C12—C171.5071 (16)
O4—C51.3886 (13)C13—C141.3892 (17)
C5—O51.2000 (13)C13—H130.9500
C5—C5A1.4815 (14)C14—C151.3919 (17)
C5A—C61.3966 (14)C14—H140.9500
C5A—C9A1.4118 (14)C15—C161.3857 (16)
C6—C71.3813 (15)C15—H150.9500
C6—H60.9500C16—H160.9500
C7—C81.3955 (16)C17—H17A0.9800
C7—H70.9500C17—H17B0.9800
C8—C91.3894 (15)C17—H17C0.9800
C8—H80.9500
N2—N1—C9B110.50 (9)C5A—C9A—C9B113.56 (9)
N2—N1—C11119.30 (9)N1—C9B—C3A102.72 (9)
C9B—N1—C11130.07 (9)N1—C9B—C9A135.95 (10)
N3—N2—N1108.05 (9)C3A—C9B—C9A121.23 (10)
N2—N3—C3A106.87 (9)C16—C11—C12122.48 (10)
N3—C3A—O4122.25 (9)C16—C11—N1117.17 (9)
N3—C3A—C9B111.86 (10)C12—C11—N1120.34 (9)
O4—C3A—C9B125.89 (10)C13—C12—C11116.72 (10)
C3A—O4—C5117.51 (8)C13—C12—C17120.71 (10)
O5—C5—O4116.76 (10)C11—C12—C17122.57 (10)
O5—C5—C5A125.01 (10)C14—C13—C12121.31 (11)
O4—C5—C5A118.20 (9)C14—C13—H13119.3
C6—C5A—C9A120.12 (10)C12—C13—H13119.3
C6—C5A—C5116.46 (9)C13—C14—C15120.69 (11)
C9A—C5A—C5123.40 (9)C13—C14—H14119.7
C7—C6—C5A120.08 (10)C15—C14—H14119.7
C7—C6—H6120.0C16—C15—C14119.18 (10)
C5A—C6—H6120.0C16—C15—H15120.4
C6—C7—C8119.97 (10)C14—C15—H15120.4
C6—C7—H7120.0C15—C16—C11119.55 (10)
C8—C7—H7120.0C15—C16—H16120.2
C9—C8—C7120.94 (10)C11—C16—H16120.2
C9—C8—H8119.5C12—C17—H17A109.5
C7—C8—H8119.5C12—C17—H17B109.5
C8—C9—C9A119.53 (10)H17A—C17—H17B109.5
C8—C9—H9120.2C12—C17—H17C109.5
C9A—C9—H9120.2H17A—C17—H17C109.5
C9—C9A—C5A119.35 (10)H17B—C17—H17C109.5
C9—C9A—C9B127.07 (10)
C9B—N1—N2—N30.61 (12)N2—N1—C9B—C9A175.50 (11)
C11—N1—N2—N3176.84 (9)C11—N1—C9B—C9A0.2 (2)
N1—N2—N3—C3A0.29 (12)N3—C3A—C9B—N10.46 (12)
N2—N3—C3A—O4179.29 (9)O4—C3A—C9B—N1179.60 (10)
N2—N3—C3A—C9B0.12 (13)N3—C3A—C9B—C9A176.40 (9)
N3—C3A—O4—C5179.41 (9)O4—C3A—C9B—C9A2.74 (16)
C9B—C3A—O4—C51.54 (15)C9—C9A—C9B—N10.72 (19)
C3A—O4—C5—O5177.28 (9)C5A—C9A—C9B—N1179.19 (11)
C3A—O4—C5—C5A4.34 (13)C9—C9A—C9B—C3A174.88 (10)
O5—C5—C5A—C62.91 (16)C5A—C9A—C9B—C3A3.59 (14)
O4—C5—C5A—C6175.32 (9)N2—N1—C11—C1662.57 (13)
O5—C5—C5A—C9A178.43 (10)C9B—N1—C11—C16112.81 (12)
O4—C5—C5A—C9A3.34 (15)N2—N1—C11—C12116.56 (11)
C9A—C5A—C6—C70.59 (16)C9B—N1—C11—C1268.06 (15)
C5—C5A—C6—C7178.11 (9)C16—C11—C12—C133.01 (16)
C5A—C6—C7—C80.43 (16)N1—C11—C12—C13177.90 (10)
C6—C7—C8—C90.35 (16)C16—C11—C12—C17176.43 (11)
C7—C8—C9—C9A0.43 (16)N1—C11—C12—C172.66 (16)
C8—C9—C9A—C5A0.58 (15)C11—C12—C13—C141.10 (17)
C8—C9—C9A—C9B178.97 (10)C17—C12—C13—C14178.35 (11)
C6—C5A—C9A—C90.67 (15)C12—C13—C14—C151.34 (18)
C5—C5A—C9A—C9177.95 (9)C13—C14—C15—C161.95 (17)
C6—C5A—C9A—C9B179.27 (9)C14—C15—C16—C110.10 (16)
C5—C5A—C9A—C9B0.65 (14)C12—C11—C16—C152.46 (16)
N2—N1—C9B—C3A0.64 (11)N1—C11—C16—C15178.43 (9)
C11—N1—C9B—C3A176.34 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7···N3i0.952.553.2770 (15)133
C13—H13···O5ii0.952.543.4083 (16)151
C15—H15···O5iii0.952.483.2482 (16)138
Symmetry codes: (i) x1, y, z1; (ii) x+1/2, y1/2, z+3/2; (iii) x+3/2, y1/2, z+3/2.
1-(3-Chlorophenyl)isochromeno[3,4-d][1,2,3]triazol-5(1H)-one (III) top
Crystal data top
C15H8ClN3O2F(000) = 608
Mr = 297.69Dx = 1.563 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 11.0993 (8) ÅCell parameters from 2905 reflections
b = 12.8996 (9) Åθ = 2.5–27.5°
c = 9.2234 (6) ŵ = 0.31 mm1
β = 106.675 (2)°T = 100 K
V = 1265.04 (15) Å3Plate, yellow
Z = 40.20 × 0.12 × 0.05 mm
Data collection top
Bruker D8 Venture
diffractometer
2905 independent reflections
Radiation source: INCOATEC high brilliance microfocus sealed tube2495 reflections with I > 2σ(I)
Multilayer mirror monochromatorRint = 0.044
φ and ω scansθmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
h = 1414
Tmin = 0.895, Tmax = 0.985k = 1616
28194 measured reflectionsl = 1111
Refinement top
Refinement on F2Primary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032H-atom parameters constrained
wR(F2) = 0.089 w = 1/[σ2(Fo2) + (0.0355P)2 + 0.8531P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max < 0.001
2905 reflectionsΔρmax = 0.32 e Å3
190 parametersΔρmin = 0.36 e Å3
0 restraints
Special details top

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 (Å2) top
xyzUiso*/Ueq
N10.31229 (11)0.37182 (9)0.35005 (13)0.0154 (2)
N20.33212 (12)0.37226 (9)0.21107 (13)0.0178 (3)
N30.45443 (12)0.37148 (9)0.23045 (13)0.0178 (3)
C3A0.50995 (13)0.37008 (10)0.38001 (15)0.0150 (3)
O40.63690 (9)0.36761 (8)0.43901 (11)0.0173 (2)
C50.68473 (13)0.35314 (11)0.59491 (16)0.0169 (3)
O50.79506 (10)0.33562 (9)0.64252 (12)0.0235 (2)
C5A0.59649 (13)0.36403 (10)0.68762 (15)0.0152 (3)
C60.64946 (14)0.36544 (11)0.84469 (16)0.0172 (3)
H60.73770.35780.88680.021*
C70.57345 (14)0.37794 (11)0.93857 (16)0.0184 (3)
H70.60920.37841.04530.022*
C80.44389 (14)0.38985 (11)0.87597 (16)0.0178 (3)
H80.39220.39910.94110.021*
C90.38931 (13)0.38851 (11)0.72091 (16)0.0168 (3)
H90.30100.39710.68020.020*
C9A0.46493 (13)0.37448 (10)0.62463 (15)0.0145 (3)
C9B0.42430 (13)0.37109 (10)0.46111 (15)0.0146 (3)
C110.18482 (13)0.37130 (11)0.35641 (15)0.0165 (3)
C120.10125 (13)0.43927 (11)0.26168 (16)0.0183 (3)
H120.12800.48480.19610.022*
C130.02249 (14)0.43847 (12)0.26588 (17)0.0217 (3)
Cl130.12819 (4)0.52194 (3)0.14523 (5)0.03006 (12)
C140.06264 (15)0.37398 (14)0.36282 (18)0.0266 (3)
H140.14740.37580.36590.032*
C150.02333 (15)0.30666 (14)0.45542 (19)0.0278 (4)
H150.00310.26230.52260.033*
C160.14708 (14)0.30312 (12)0.45149 (17)0.0217 (3)
H160.20480.25520.51240.026*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0152 (6)0.0181 (6)0.0128 (5)0.0003 (4)0.0039 (4)0.0002 (4)
N20.0201 (6)0.0196 (6)0.0146 (6)0.0005 (5)0.0062 (5)0.0001 (4)
N30.0191 (6)0.0184 (6)0.0163 (6)0.0005 (5)0.0055 (5)0.0004 (4)
C3A0.0161 (7)0.0142 (6)0.0151 (6)0.0002 (5)0.0052 (5)0.0001 (5)
O40.0145 (5)0.0217 (5)0.0165 (5)0.0004 (4)0.0057 (4)0.0001 (4)
C50.0172 (7)0.0161 (6)0.0173 (7)0.0017 (5)0.0047 (5)0.0009 (5)
O50.0152 (5)0.0317 (6)0.0236 (5)0.0013 (4)0.0058 (4)0.0006 (4)
C5A0.0163 (7)0.0134 (6)0.0161 (7)0.0009 (5)0.0049 (5)0.0002 (5)
C60.0155 (7)0.0161 (6)0.0183 (7)0.0011 (5)0.0020 (5)0.0004 (5)
C70.0221 (7)0.0182 (7)0.0138 (6)0.0010 (5)0.0036 (5)0.0005 (5)
C80.0218 (7)0.0171 (7)0.0159 (6)0.0001 (5)0.0078 (5)0.0001 (5)
C90.0153 (7)0.0177 (7)0.0179 (7)0.0005 (5)0.0056 (5)0.0002 (5)
C9A0.0168 (7)0.0133 (6)0.0134 (6)0.0006 (5)0.0044 (5)0.0003 (5)
C9B0.0152 (6)0.0136 (6)0.0150 (6)0.0008 (5)0.0042 (5)0.0002 (5)
C110.0141 (7)0.0197 (7)0.0150 (6)0.0016 (5)0.0032 (5)0.0029 (5)
C120.0181 (7)0.0203 (7)0.0162 (6)0.0007 (5)0.0046 (5)0.0015 (5)
C130.0174 (7)0.0274 (8)0.0182 (7)0.0024 (6)0.0018 (5)0.0002 (6)
Cl130.0192 (2)0.0406 (2)0.0283 (2)0.00990 (16)0.00339 (15)0.00611 (16)
C140.0167 (7)0.0377 (9)0.0255 (8)0.0022 (6)0.0065 (6)0.0008 (7)
C150.0230 (8)0.0359 (9)0.0250 (8)0.0059 (7)0.0077 (6)0.0058 (7)
C160.0201 (7)0.0238 (7)0.0196 (7)0.0024 (6)0.0033 (6)0.0031 (6)
Geometric parameters (Å, º) top
N1—N21.3614 (16)C8—C91.3841 (19)
N1—C9B1.3654 (18)C8—H80.9500
N1—C111.4328 (18)C9—C9A1.3977 (19)
N2—N31.3175 (17)C9—H90.9500
N3—C3A1.3399 (18)C9A—C9B1.4455 (18)
C3A—O41.3574 (17)C11—C121.388 (2)
C3A—C9B1.3680 (19)C11—C161.389 (2)
O4—C51.3950 (17)C12—C131.385 (2)
C5—O51.1979 (18)C12—H120.9500
C5—C5A1.4801 (19)C13—C141.385 (2)
C5A—C61.3986 (19)C13—Cl131.7392 (15)
C5A—C9A1.4146 (19)C14—C151.388 (2)
C6—C71.381 (2)C14—H140.9500
C6—H60.9500C15—C161.385 (2)
C7—C81.396 (2)C15—H150.9500
C7—H70.9500C16—H160.9500
N2—N1—C9B110.37 (11)C9A—C9—H9120.2
N2—N1—C11117.83 (11)C9—C9A—C5A119.26 (13)
C9B—N1—C11131.80 (12)C9—C9A—C9B127.04 (13)
N3—N2—N1108.11 (11)C5A—C9A—C9B113.69 (12)
N2—N3—C3A106.94 (12)N1—C9B—C3A102.46 (12)
N3—C3A—O4122.07 (12)N1—C9B—C9A136.62 (13)
N3—C3A—C9B112.11 (13)C3A—C9B—C9A120.87 (13)
O4—C3A—C9B125.82 (12)C12—C11—C16121.95 (14)
C3A—O4—C5117.43 (11)C12—C11—N1117.43 (12)
O5—C5—O4116.73 (12)C16—C11—N1120.60 (13)
O5—C5—C5A125.62 (13)C13—C12—C11117.81 (14)
O4—C5—C5A117.62 (12)C13—C12—H12121.1
C6—C5A—C9A120.11 (13)C11—C12—H12121.1
C6—C5A—C5116.65 (12)C12—C13—C14121.86 (14)
C9A—C5A—C5123.23 (12)C12—C13—Cl13118.02 (12)
C7—C6—C5A120.01 (13)C14—C13—Cl13120.12 (12)
C7—C6—H6120.0C13—C14—C15118.77 (15)
C5A—C6—H6120.0C13—C14—H14120.6
C6—C7—C8119.72 (13)C15—C14—H14120.6
C6—C7—H7120.1C16—C15—C14121.09 (15)
C8—C7—H7120.1C16—C15—H15119.5
C9—C8—C7121.31 (13)C14—C15—H15119.5
C9—C8—H8119.3C15—C16—C11118.47 (14)
C7—C8—H8119.3C15—C16—H16120.8
C8—C9—C9A119.57 (13)C11—C16—H16120.8
C8—C9—H9120.2
C9B—N1—N2—N30.20 (15)C11—N1—C9B—C3A178.81 (14)
C11—N1—N2—N3179.28 (11)N2—N1—C9B—C9A176.95 (15)
N1—N2—N3—C3A0.28 (14)C11—N1—C9B—C9A3.7 (3)
N2—N3—C3A—O4179.12 (12)N3—C3A—C9B—N10.77 (15)
N2—N3—C3A—C9B0.68 (16)O4—C3A—C9B—N1179.02 (13)
N3—C3A—O4—C5172.11 (12)N3—C3A—C9B—C9A177.25 (12)
C9B—C3A—O4—C57.7 (2)O4—C3A—C9B—C9A3.0 (2)
C3A—O4—C5—O5169.17 (13)C9—C9A—C9B—N15.6 (3)
C3A—O4—C5—C5A12.78 (17)C5A—C9A—C9B—N1175.67 (15)
O5—C5—C5A—C67.6 (2)C9—C9A—C9B—C3A171.59 (14)
O4—C5—C5A—C6170.28 (12)C5A—C9A—C9B—C3A7.14 (19)
O5—C5—C5A—C9A173.50 (14)N2—N1—C11—C1245.43 (17)
O4—C5—C5A—C9A8.6 (2)C9B—N1—C11—C12135.22 (15)
C9A—C5A—C6—C70.6 (2)N2—N1—C11—C16132.99 (14)
C5—C5A—C6—C7178.40 (13)C9B—N1—C11—C1646.4 (2)
C5A—C6—C7—C80.4 (2)C16—C11—C12—C130.9 (2)
C6—C7—C8—C90.6 (2)N1—C11—C12—C13179.30 (13)
C7—C8—C9—C9A0.3 (2)C11—C12—C13—C141.3 (2)
C8—C9—C9A—C5A1.3 (2)C11—C12—C13—Cl13178.97 (11)
C8—C9—C9A—C9B179.96 (13)C12—C13—C14—C151.6 (2)
C6—C5A—C9A—C91.4 (2)Cl13—C13—C14—C15178.64 (13)
C5—C5A—C9A—C9177.46 (13)C13—C14—C15—C160.2 (3)
C6—C5A—C9A—C9B179.74 (12)C14—C15—C16—C112.3 (2)
C5—C5A—C9A—C9B1.38 (19)C12—C11—C16—C152.6 (2)
N2—N1—C9B—C3A0.58 (15)N1—C11—C16—C15179.00 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8···N3i0.952.583.2465 (19)127
C16—H16···N2ii0.952.563.500 (2)169
Symmetry codes: (i) x, y, z+1; (ii) x, y+1/2, z+1/2.
1-(4-Chlorophenyl)isochromeno[3,4-d][1,2,3]triazol-5(1H)-one (IV) top
Crystal data top
C15H8ClN3O2F(000) = 608
Mr = 297.69Dx = 1.570 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 16.7331 (12) ÅCell parameters from 2892 reflections
b = 5.9676 (4) Åθ = 2.6–27.5°
c = 13.681 (1) ŵ = 0.31 mm1
β = 112.820 (3)°T = 100 K
V = 1259.21 (16) Å3Block, pink
Z = 40.25 × 0.14 × 0.11 mm
Data collection top
Bruker D8 Venture
diffractometer
2891 independent reflections
Radiation source: INCOATEC high brilliance microfocus sealed tube2413 reflections with I > 2σ(I)
Multilayer mirror monochromatorRint = 0.056
φ and ω scansθmax = 27.5°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
h = 2121
Tmin = 0.880, Tmax = 0.967k = 77
34775 measured reflectionsl = 1717
Refinement top
Refinement on F2Primary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034H-atom parameters constrained
wR(F2) = 0.087 w = 1/[σ2(Fo2) + (0.0251P)2 + 1.2186P]
where P = (Fo2 + 2Fc2)/3
S = 1.12(Δ/σ)max < 0.001
2891 reflectionsΔρmax = 0.37 e Å3
190 parametersΔρmin = 0.26 e Å3
0 restraints
Special details top

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 (Å2) top
xyzUiso*/Ueq
N10.28243 (8)0.9201 (2)0.34381 (11)0.0144 (3)
N20.31078 (9)1.1119 (2)0.40077 (11)0.0171 (3)
N30.27667 (9)1.1220 (2)0.47311 (11)0.0167 (3)
C3A0.22867 (10)0.9365 (3)0.46143 (12)0.0148 (3)
O40.18490 (7)0.89279 (19)0.52497 (9)0.0165 (2)
C50.13882 (10)0.6934 (3)0.50868 (13)0.0164 (3)
O50.10574 (8)0.6503 (2)0.57022 (10)0.0229 (3)
C5A0.13207 (10)0.5537 (3)0.41602 (12)0.0144 (3)
C60.07782 (10)0.3663 (3)0.39504 (13)0.0167 (3)
H60.04830.33160.44010.020*
C70.06720 (11)0.2317 (3)0.30858 (13)0.0179 (3)
H70.03090.10330.29480.021*
C80.10969 (10)0.2841 (3)0.24148 (13)0.0165 (3)
H80.10130.19210.18160.020*
C90.16389 (10)0.4687 (3)0.26127 (13)0.0149 (3)
H90.19260.50280.21520.018*
C9A0.17630 (10)0.6048 (3)0.34916 (12)0.0136 (3)
C9B0.22950 (10)0.8037 (3)0.38052 (12)0.0138 (3)
C110.32143 (10)0.8577 (3)0.27144 (13)0.0140 (3)
C120.36182 (10)0.6505 (3)0.28242 (13)0.0162 (3)
H120.35940.54570.33350.019*
C130.40594 (10)0.5987 (3)0.21758 (13)0.0162 (3)
H130.43290.45660.22270.019*
C140.41012 (10)0.7567 (3)0.14533 (13)0.0158 (3)
Cl140.47074 (3)0.69834 (7)0.07027 (3)0.02089 (12)
C150.36852 (11)0.9621 (3)0.13295 (13)0.0170 (3)
H150.37091.06670.08180.020*
C160.32319 (10)1.0128 (3)0.19655 (13)0.0160 (3)
H160.29381.15200.18890.019*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0145 (6)0.0119 (6)0.0174 (7)0.0002 (5)0.0067 (5)0.0001 (5)
N20.0175 (7)0.0139 (7)0.0189 (7)0.0001 (5)0.0059 (6)0.0025 (5)
N30.0168 (7)0.0155 (7)0.0167 (7)0.0012 (5)0.0054 (5)0.0016 (5)
C3A0.0142 (7)0.0152 (7)0.0147 (7)0.0019 (6)0.0051 (6)0.0007 (6)
O40.0200 (6)0.0170 (6)0.0151 (5)0.0010 (5)0.0097 (5)0.0023 (4)
C50.0146 (8)0.0176 (8)0.0169 (8)0.0023 (6)0.0059 (6)0.0010 (6)
O50.0248 (7)0.0287 (7)0.0201 (6)0.0039 (5)0.0141 (5)0.0030 (5)
C5A0.0134 (7)0.0155 (8)0.0139 (7)0.0023 (6)0.0049 (6)0.0015 (6)
C60.0149 (8)0.0170 (8)0.0182 (8)0.0006 (6)0.0065 (6)0.0028 (6)
C70.0157 (8)0.0150 (8)0.0203 (8)0.0011 (6)0.0040 (7)0.0018 (6)
C80.0162 (8)0.0142 (7)0.0159 (8)0.0017 (6)0.0029 (6)0.0021 (6)
C90.0153 (8)0.0141 (7)0.0150 (7)0.0012 (6)0.0057 (6)0.0008 (6)
C9A0.0128 (7)0.0125 (7)0.0142 (7)0.0023 (6)0.0039 (6)0.0020 (6)
C9B0.0135 (7)0.0139 (7)0.0146 (7)0.0013 (6)0.0060 (6)0.0004 (6)
C110.0108 (7)0.0153 (7)0.0163 (7)0.0024 (6)0.0056 (6)0.0015 (6)
C120.0151 (8)0.0160 (8)0.0165 (8)0.0008 (6)0.0050 (6)0.0016 (6)
C130.0142 (7)0.0139 (7)0.0191 (8)0.0021 (6)0.0051 (6)0.0004 (6)
C140.0126 (7)0.0199 (8)0.0150 (8)0.0027 (6)0.0053 (6)0.0031 (6)
Cl140.0205 (2)0.0249 (2)0.0211 (2)0.00127 (16)0.01233 (16)0.00372 (16)
C150.0183 (8)0.0170 (8)0.0153 (8)0.0017 (6)0.0062 (6)0.0019 (6)
C160.0155 (8)0.0132 (7)0.0185 (8)0.0016 (6)0.0056 (6)0.0018 (6)
Geometric parameters (Å, º) top
N1—N21.3625 (19)C8—C91.386 (2)
N1—C9B1.365 (2)C8—H80.9500
N1—C111.430 (2)C9—C9A1.398 (2)
N2—N31.3217 (19)C9—H90.9500
N3—C3A1.341 (2)C9A—C9B1.445 (2)
C3A—O41.3615 (19)C11—C121.389 (2)
C3A—C9B1.366 (2)C11—C161.390 (2)
O4—C51.388 (2)C12—C131.391 (2)
C5—O51.201 (2)C12—H120.9500
C5—C5A1.485 (2)C13—C141.387 (2)
C5A—C61.398 (2)C13—H130.9500
C5A—C9A1.415 (2)C14—C151.387 (2)
C6—C71.383 (2)C14—Cl141.7358 (16)
C6—H60.9500C15—C161.391 (2)
C7—C81.397 (2)C15—H150.9500
C7—H70.9500C16—H160.9500
N2—N1—C9B110.42 (13)C9A—C9—H9120.1
N2—N1—C11117.62 (13)C9—C9A—C5A119.34 (14)
C9B—N1—C11131.09 (13)C9—C9A—C9B126.95 (14)
N3—N2—N1108.11 (13)C5A—C9A—C9B113.69 (14)
N2—N3—C3A106.61 (13)N1—C9B—C3A102.40 (14)
N3—C3A—O4121.86 (14)N1—C9B—C9A136.18 (14)
N3—C3A—C9B112.45 (14)C3A—C9B—C9A121.21 (14)
O4—C3A—C9B125.69 (15)C12—C11—C16121.61 (15)
C3A—O4—C5117.68 (12)C12—C11—N1119.38 (14)
O5—C5—O4116.70 (15)C16—C11—N1118.85 (14)
O5—C5—C5A125.10 (15)C11—C12—C13119.03 (15)
O4—C5—C5A118.18 (13)C11—C12—H12120.5
C6—C5A—C9A120.04 (15)C13—C12—H12120.5
C6—C5A—C5116.93 (14)C14—C13—C12119.27 (15)
C9A—C5A—C5123.02 (14)C14—C13—H13120.4
C7—C6—C5A119.86 (15)C12—C13—H13120.4
C7—C6—H6120.1C15—C14—C13121.75 (15)
C5A—C6—H6120.1C15—C14—Cl14119.07 (13)
C6—C7—C8120.19 (15)C13—C14—Cl14119.17 (13)
C6—C7—H7119.9C14—C15—C16119.03 (15)
C8—C7—H7119.9C14—C15—H15120.5
C9—C8—C7120.71 (15)C16—C15—H15120.5
C9—C8—H8119.6C11—C16—C15119.26 (15)
C7—C8—H8119.6C11—C16—H16120.4
C8—C9—C9A119.85 (15)C15—C16—H16120.4
C8—C9—H9120.1
C9B—N1—N2—N30.38 (17)C11—N1—C9B—C3A168.64 (15)
C11—N1—N2—N3170.86 (13)N2—N1—C9B—C9A174.36 (17)
N1—N2—N3—C3A0.74 (17)C11—N1—C9B—C9A16.8 (3)
N2—N3—C3A—O4179.27 (13)N3—C3A—C9B—N10.63 (18)
N2—N3—C3A—C9B0.88 (18)O4—C3A—C9B—N1179.53 (14)
N3—C3A—O4—C5178.29 (14)N3—C3A—C9B—C9A174.93 (14)
C9B—C3A—O4—C51.9 (2)O4—C3A—C9B—C9A4.9 (2)
C3A—O4—C5—O5174.88 (14)C9—C9A—C9B—N11.2 (3)
C3A—O4—C5—C5A6.7 (2)C5A—C9A—C9B—N1179.60 (17)
O5—C5—C5A—C64.8 (2)C9—C9A—C9B—C3A172.55 (16)
O4—C5—C5A—C6173.41 (14)C5A—C9A—C9B—C3A5.9 (2)
O5—C5—C5A—C9A176.28 (16)N2—N1—C11—C12122.23 (16)
O4—C5—C5A—C9A5.5 (2)C9B—N1—C11—C1245.9 (2)
C9A—C5A—C6—C70.3 (2)N2—N1—C11—C1653.3 (2)
C5—C5A—C6—C7178.64 (15)C9B—N1—C11—C16138.61 (17)
C5A—C6—C7—C80.8 (2)C16—C11—C12—C130.8 (2)
C6—C7—C8—C91.0 (2)N1—C11—C12—C13174.59 (14)
C7—C8—C9—C9A0.1 (2)C11—C12—C13—C141.4 (2)
C8—C9—C9A—C5A1.0 (2)C12—C13—C14—C152.6 (2)
C8—C9—C9A—C9B179.30 (15)C12—C13—C14—Cl14176.09 (12)
C6—C5A—C9A—C91.1 (2)C13—C14—C15—C161.6 (2)
C5—C5A—C9A—C9177.70 (14)Cl14—C14—C15—C16177.12 (12)
C6—C5A—C9A—C9B179.70 (14)C12—C11—C16—C151.8 (2)
C5—C5A—C9A—C9B0.9 (2)N1—C11—C16—C15173.59 (14)
N2—N1—C9B—C3A0.14 (17)C14—C15—C16—C110.6 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O5i0.952.533.287 (2)137
C8—H8···O5ii0.952.573.478 (2)161
C15—H15···N3iii0.952.523.271 (2)136
C7—H7···Cg1iv0.952.693.517 (2)146
Symmetry codes: (i) x, y+1, z+1; (ii) x, y+1/2, z1/2; (iii) x, y+5/2, z1/2; (iv) x, y1/2, z+1/2.
Methyl 2-[4-hydroxy-1-(2-methylphenyl)-1H-1,2,3-triazol-5-yl]benzoate (V) top
Crystal data top
C17H15N3O3F(000) = 648
Mr = 309.32Dx = 1.405 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 11.1518 (5) ÅCell parameters from 3361 reflections
b = 9.3143 (4) Åθ = 2.6–27.5°
c = 14.2417 (6) ŵ = 0.10 mm1
β = 98.655 (2)°T = 100 K
V = 1462.46 (11) Å3Block, colourless
Z = 40.19 × 0.11 × 0.07 mm
Data collection top
Bruker D8 Venture
diffractometer
3360 independent reflections
Radiation source: INCOATEC high brilliance microfocus sealed tube3084 reflections with I > 2σ(I)
Multilayer mirror monochromatorRint = 0.036
φ and ω scansθmax = 27.5°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
h = 1414
Tmin = 0.960, Tmax = 0.993k = 1212
33834 measured reflectionsl = 1818
Refinement top
Refinement on F2Primary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.042H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.098 w = 1/[σ2(Fo2) + (0.0333P)2 + 1.1492P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
3360 reflectionsΔρmax = 0.34 e Å3
213 parametersΔρmin = 0.22 e Å3
0 restraints
Special details top

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 (Å2) top
xyzUiso*/Ueq
C10.09089 (12)0.58783 (14)0.64445 (9)0.0143 (3)
C20.20897 (12)0.64468 (14)0.66637 (9)0.0140 (3)
C30.22319 (12)0.79047 (15)0.68731 (9)0.0171 (3)
H30.30240.82950.70270.021*
C40.12250 (13)0.87957 (15)0.68594 (10)0.0194 (3)
H40.13330.97890.69980.023*
C50.00649 (13)0.82309 (16)0.66441 (10)0.0194 (3)
H50.06220.88370.66330.023*
C60.00894 (12)0.67859 (15)0.64454 (9)0.0176 (3)
H60.08860.64030.63070.021*
C70.07137 (12)0.43259 (15)0.61927 (9)0.0158 (3)
O10.15037 (9)0.34535 (11)0.61744 (8)0.0255 (2)
O20.04681 (9)0.40148 (11)0.59904 (7)0.0205 (2)
C80.07555 (14)0.25126 (16)0.58262 (11)0.0227 (3)
H8A0.05540.19800.64230.034*
H8B0.02840.21310.53550.034*
H8C0.16230.24100.55900.034*
N210.38126 (10)0.47254 (12)0.72720 (8)0.0142 (2)
N220.47490 (10)0.40735 (12)0.69580 (8)0.0160 (2)
N230.47309 (10)0.45003 (12)0.60673 (8)0.0157 (2)
C240.38003 (11)0.54203 (14)0.58314 (9)0.0152 (3)
C250.31891 (11)0.55871 (14)0.65953 (9)0.0140 (3)
C2110.35990 (11)0.44834 (15)0.82315 (9)0.0155 (3)
C2120.33495 (12)0.30970 (15)0.85228 (9)0.0171 (3)
C2130.31541 (12)0.29355 (16)0.94627 (10)0.0210 (3)
H2130.29810.20090.96880.025*
C2140.32075 (13)0.40992 (18)1.00731 (10)0.0241 (3)
H2140.30620.39621.07070.029*
C2150.34696 (14)0.54549 (17)0.97710 (10)0.0235 (3)
H2150.35130.62461.01960.028*
C2160.36705 (12)0.56555 (15)0.88384 (10)0.0191 (3)
H2160.38540.65820.86210.023*
C2170.32682 (14)0.18273 (15)0.78655 (10)0.0226 (3)
H27A0.30300.09750.81960.034*
H27B0.40600.16610.76650.034*
H27C0.26620.20180.73060.034*
O240.35119 (9)0.60183 (12)0.49726 (7)0.0208 (2)
H240.4112 (18)0.587 (2)0.4622 (14)0.031*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0154 (6)0.0175 (6)0.0104 (6)0.0008 (5)0.0028 (4)0.0018 (5)
C20.0145 (6)0.0172 (6)0.0109 (5)0.0013 (5)0.0035 (4)0.0013 (5)
C30.0158 (6)0.0192 (7)0.0161 (6)0.0011 (5)0.0016 (5)0.0004 (5)
C40.0225 (7)0.0169 (6)0.0188 (6)0.0017 (5)0.0036 (5)0.0024 (5)
C50.0178 (6)0.0228 (7)0.0179 (6)0.0056 (5)0.0034 (5)0.0006 (5)
C60.0139 (6)0.0229 (7)0.0160 (6)0.0010 (5)0.0022 (5)0.0012 (5)
C70.0162 (6)0.0190 (6)0.0119 (6)0.0011 (5)0.0009 (5)0.0021 (5)
O10.0179 (5)0.0191 (5)0.0386 (6)0.0015 (4)0.0014 (4)0.0051 (4)
O20.0152 (5)0.0189 (5)0.0268 (5)0.0028 (4)0.0010 (4)0.0002 (4)
C80.0231 (7)0.0196 (7)0.0248 (7)0.0066 (5)0.0013 (6)0.0001 (6)
N210.0122 (5)0.0158 (5)0.0148 (5)0.0015 (4)0.0031 (4)0.0013 (4)
N220.0139 (5)0.0187 (5)0.0164 (5)0.0022 (4)0.0049 (4)0.0011 (4)
N230.0148 (5)0.0186 (6)0.0141 (5)0.0011 (4)0.0036 (4)0.0010 (4)
C240.0134 (6)0.0169 (6)0.0155 (6)0.0004 (5)0.0027 (5)0.0002 (5)
C250.0125 (6)0.0149 (6)0.0142 (6)0.0007 (5)0.0011 (4)0.0003 (5)
C2110.0113 (6)0.0216 (7)0.0137 (6)0.0027 (5)0.0022 (4)0.0029 (5)
C2120.0121 (6)0.0207 (7)0.0179 (6)0.0018 (5)0.0004 (5)0.0033 (5)
C2130.0166 (6)0.0250 (7)0.0210 (7)0.0014 (5)0.0012 (5)0.0085 (6)
C2140.0234 (7)0.0343 (8)0.0151 (6)0.0065 (6)0.0046 (5)0.0059 (6)
C2150.0257 (7)0.0279 (8)0.0165 (7)0.0072 (6)0.0019 (5)0.0016 (6)
C2160.0191 (6)0.0194 (7)0.0184 (6)0.0037 (5)0.0015 (5)0.0020 (5)
C2170.0264 (7)0.0180 (7)0.0231 (7)0.0005 (6)0.0023 (6)0.0024 (6)
O240.0199 (5)0.0299 (6)0.0138 (5)0.0093 (4)0.0068 (4)0.0063 (4)
Geometric parameters (Å, º) top
C1—C61.3981 (18)N21—C2111.4396 (16)
C1—C21.4100 (18)N22—N231.3265 (15)
C1—C71.4977 (19)N23—C241.3489 (17)
C2—C31.3941 (19)C24—O241.3383 (16)
C2—C251.4798 (17)C24—C251.3768 (17)
C3—C41.3941 (19)C211—C2161.3873 (19)
C3—H30.9500C211—C2121.3971 (19)
C4—C51.387 (2)C212—C2131.3963 (19)
C4—H40.9500C212—C2171.503 (2)
C5—C61.381 (2)C213—C2141.385 (2)
C5—H50.9500C213—H2130.9500
C6—H60.9500C214—C2151.379 (2)
C7—O11.2017 (17)C214—H2140.9500
C7—O21.3378 (16)C215—C2161.3924 (19)
O2—C81.4466 (17)C215—H2150.9500
C8—H8A0.9800C216—H2160.9500
C8—H8B0.9800C217—H27A0.9800
C8—H8C0.9800C217—H27B0.9800
N21—N221.3415 (15)C217—H27C0.9800
N21—C251.3619 (16)O24—H240.90 (2)
C6—C1—C2119.34 (12)N22—N23—C24109.21 (10)
C6—C1—C7119.80 (12)O24—C24—N23124.20 (12)
C2—C1—C7120.85 (12)O24—C24—C25126.57 (12)
C3—C2—C1119.05 (12)N23—C24—C25109.19 (11)
C3—C2—C25118.19 (12)N21—C25—C24103.41 (11)
C1—C2—C25122.52 (12)N21—C25—C2127.75 (11)
C4—C3—C2120.76 (13)C24—C25—C2128.80 (12)
C4—C3—H3119.6C216—C211—C212122.52 (12)
C2—C3—H3119.6C216—C211—N21117.77 (12)
C5—C4—C3119.98 (13)C212—C211—N21119.70 (12)
C5—C4—H4120.0C213—C212—C211116.82 (13)
C3—C4—H4120.0C213—C212—C217120.60 (13)
C6—C5—C4119.88 (13)C211—C212—C217122.58 (12)
C6—C5—H5120.1C214—C213—C212121.27 (14)
C4—C5—H5120.1C214—C213—H213119.4
C5—C6—C1120.99 (13)C212—C213—H213119.4
C5—C6—H6119.5C215—C214—C213120.78 (13)
C1—C6—H6119.5C215—C214—H214119.6
O1—C7—O2123.40 (13)C213—C214—H214119.6
O1—C7—C1125.27 (12)C214—C215—C216119.50 (14)
O2—C7—C1111.32 (11)C214—C215—H215120.3
C7—O2—C8115.56 (11)C216—C215—H215120.3
O2—C8—H8A109.5C211—C216—C215119.10 (13)
O2—C8—H8B109.5C211—C216—H216120.5
H8A—C8—H8B109.5C215—C216—H216120.5
O2—C8—H8C109.5C212—C217—H27A109.5
H8A—C8—H8C109.5C212—C217—H27B109.5
H8B—C8—H8C109.5H27A—C217—H27B109.5
N22—N21—C25111.77 (10)C212—C217—H27C109.5
N22—N21—C211119.60 (10)H27A—C217—H27C109.5
C25—N21—C211128.62 (11)H27B—C217—H27C109.5
N23—N22—N21106.42 (10)C24—O24—H24110.1 (12)
C6—C1—C2—C30.23 (18)C211—N21—C25—C23.2 (2)
C7—C1—C2—C3178.54 (12)O24—C24—C25—N21177.72 (13)
C6—C1—C2—C25174.48 (12)N23—C24—C25—N210.04 (14)
C7—C1—C2—C254.29 (18)O24—C24—C25—C20.1 (2)
C1—C2—C3—C40.53 (19)N23—C24—C25—C2177.80 (13)
C25—C2—C3—C4173.97 (12)C3—C2—C25—N2198.58 (16)
C2—C3—C4—C50.6 (2)C1—C2—C25—N2187.12 (17)
C3—C4—C5—C60.1 (2)C3—C2—C25—C2484.07 (18)
C4—C5—C6—C10.9 (2)C1—C2—C25—C2490.23 (18)
C2—C1—C6—C50.94 (19)N22—N21—C211—C216117.83 (14)
C7—C1—C6—C5177.84 (12)C25—N21—C211—C21660.69 (18)
C6—C1—C7—O1179.60 (13)N22—N21—C211—C21261.17 (16)
C2—C1—C7—O11.6 (2)C25—N21—C211—C212120.30 (15)
C6—C1—C7—O20.11 (17)C216—C211—C212—C2130.88 (19)
C2—C1—C7—O2178.66 (11)N21—C211—C212—C213179.84 (11)
O1—C7—O2—C85.37 (19)C216—C211—C212—C217179.82 (13)
C1—C7—O2—C8174.35 (11)N21—C211—C212—C2171.23 (19)
C25—N21—N22—N230.60 (14)C211—C212—C213—C2140.0 (2)
C211—N21—N22—N23179.36 (11)C217—C212—C213—C214179.00 (13)
N21—N22—N23—C240.61 (14)C212—C213—C214—C2150.7 (2)
N22—N23—C24—O24178.16 (12)C213—C214—C215—C2160.7 (2)
N22—N23—C24—C250.41 (15)C212—C211—C216—C2151.0 (2)
N22—N21—C25—C240.34 (14)N21—C211—C216—C215179.93 (12)
C211—N21—C25—C24178.96 (12)C214—C215—C216—C2110.2 (2)
N22—N21—C25—C2178.22 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O24—H24···N23i0.90 (2)1.77 (2)2.6721 (15)177.5 (19)
C8—H8A···Cg2ii0.982.903.6605 (16)135
C8—H8B···Cg2iii0.982.903.5007 (16)120
C8—H8C···O24iii0.982.593.4004 (19)140
C215—H215···O24iv0.952.573.2972 (19)134
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y1/2, z+3/2; (iii) x, y+1, z+1; (iv) x, y+3/2, z+1/2.
Hydrogen bonds and short intermolecular contacts (Å, °) for compounds (I)-(V) top
CompoundD—H···AD—HH···AD···AD—H···A
(I)C8—H8···N3i0.952.523.4641 (16)173
C12—H12···O5ii0.952.503.4136 (16)161
(II)C7—H7···N3iii0.952.553.2770 (15)133
C13—H13···O5iv0.952.543.4083 (16)151
C15—H15···O5v0.952.483.2482 (16)138
(III)C8—H8···N3vi0.952.583.2465 (19)127
C16—H16···N2vii0.952.563.500 (2)169
(IV)C6—H6···O5viii0.952.533.287 (3)137
C8—H8···O5ix0.952.573.578 (2)161
C15—H15···N3x0.952.523.271 (2)136
C7—H7···Cg1xi0.952.693.517 (2)146
(V)O24—H24···N23xii0.90 (2)1.77 (2)2.6721 (15)177.5 (19)
C8—H8A···Cg2xiii0.982.903.6605 (16)135
C8—H8B···Cg2viii0.982.903.5007 (16)120
C8—H8C···O24viii0.982.593.4004 (19)140
C215—H215···O24xiv0.952.573.2972 (19)134
Cg1 and Cg2 represent the centroids of the rings C5A/C6–C9/C9A and C1–C6, respectively.

Symmetry codes: (i) x+1/2, -y+1/2, z+1/2; (ii) -x+1/2, y+1/2, -z+1/2; (iii) x-1, y, z-1; (iv) -x+1/2, y-1/2, -z+3/2; (v) -x+3/2, y-1/2, -z+3/2; (vi) x, y, z+1; (vii) x, -y+1/2, z+1/2; (viii) -x, -y+1, -z+1; (ix) x, -y+1/2, z-1/2; (x) x, -y+5/2, z-1/2; (xi) -x, y-1/2, -z+1/2; (xii) -x+1, -y+1, -z+1; (xiii) -x, y-1/2, -z+3/2; (xiv) x, -y+3/2, z+1/2.
 

Acknowledgements

The authors thank `Centro de Instrumentación Científico-Técnica of Universidad de Jaén' for data collection. The authors thank Universidad de Ciencias Aplicadas y Ambientales (UDCA), Universidad Nacional de Colombia, the Consejería de Innovación, Ciencia y Empresa (Junta de Andalucía, Spain) and the Universidad de Jaén for financial support.

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