In the title compound, the dihedral angle between the fused pyrazole and pyridine rings is 3.81 (9)°. The benzene ring forms dihedral angles of 35.08 (10) and 36.26 (9)° with the pyrazole and pyridine rings, respectively. In the crystal, weak C—H⋯O hydrogen bonds connect molecules along [100].
Keywords: crystal structure, pyrazolopyridine, biological activity
Abstract
In the title compound, C18H18ClN3O2S, the dihedral angle between the fused pyrazole and pyridine rings is 3.81 (9)°. The benzene ring forms dihedral angles of 35.08 (10) and 36.26 (9)° with the pyrazole and pyridine rings, respectively. In the crystal, weak C—H⋯O hydrogen bonds connect molecules along [100].
Chemical context
The nitrogen-containing heterocyclic motif is a component in many medicinally important drugs. Molecules built around the pyrazolopyridine core structure exhibit diverse medicinal properties that include anti-microbial, anti-viral, anti-fungal, anti-hypertensive, analgesic, anti-cancer, anti-inflammatory, anti-Alzheimer’s, anti-diabetic, anti-nociceptive, anti-tuberculosis, and anti-leishmanial activities (Hardy, 1984 ▸; Hawas et al. 2019 ▸; de Mello et al. 2004 ▸; Panchal et al. 2019 ▸; El-Gohary et al. 2019 ▸). In addition, some pyrazolopyridines have found uses for the treatment of hemorrhagic stress, infertility, and drug addiction (Parmar et al. 1974 ▸). Specifically, they act as inhibitors of enzymes such as glycogen synthase kinase-3 (Witherington et al. 2003 ▸) and as inhibitors for adenosine receptors (Timóteo et al. 2008 ▸). Furthermore, they have been identified as promising inhibitors of cycline dependent kinase, xanthine oxidase, interleukin-6 (IL-6), tumor necrosis factor alpha (TNF-α), phosphodiesterase-4, NAD(P)H oxidases and cholesterol formation (Gökhan-Kelekçi et al. 2007 ▸; Panchal et al. 2019 ▸; Fathy et al. 2015 ▸). Considering the aforementioned importance of derivatives of pyrazolopyridine, we have carried out a single-crystal X-ray diffraction study on the title compound and have analyzed the structure in terms of geometrical parameters, conformation, and intermolecular hydrogen-bonding interactions.
Structural commentary
The title compound has pyrazole[3,4-b]pyridine motif that is decorated by several substituents shown in Fig. 1 ▸. The chlorophenyl (C6H4Cl) group attached to the pyrazolopyridine moiety exhibits an (−)anticlinal conformation [N3—C7—C6—C3 = −141.96 (19)°], as does the methylthio (SCH3) group attached to the pyrazolopyridine unit [C11—S1—C12—C13 = −128.93 (15) °] while the –COOC2H5 group attached to the pyrazolopyridine moiety has an (+)anti-periplanar conformation [N1—C14—C13—C16 = 177.00 (15)°, as do the methyl group attached to the pyridine sub-structure [C9—N1—C14—C15 = −176.20 (16)°] and the methyl group attached to the pyrazole ring (NCH3) [C10—N2—C9—C8: −178.42 (19)°]. The fused pyrazole and pyridine rings are not exactly planar, subtending a dihedral angle of 3.81 (9)°. The dihedral angle between the planes of the benzene and pyrazole rings is 35.08 (10)° and that between the benzene and pyridine rings is 36.26 (9)°.
Figure 1.
The molecular structure of the title compound with the atom-numbering scheme and displacement ellipsoids drawn at the 50% probability level
Supramolecular features
In the crystal, weak C—H⋯O hydrogen bonds link molecules into chains along [100] (Table 1 ▸ and Fig. 2 ▸).
Table 1. Hydrogen-bond geometry (Å, °).
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| C2—H2⋯O1i | 0.93 | 2.59 | 3.513 (2) | 170 |
Symmetry code: (i) 
.
Figure 2.
The crystal packing of title compound, viewed along the c axis, showing the weak intermolecular C—H⋯O hydrogen bonds as dotted lines
Database survey
A search for the pyrazolopyridine scaffold in the Cambridge Structural Database (CSD, Version 5.40; Groom et al., 2016 ▸) gave 236 hits. Of these, the structures most closely related to the title compound are FIZLEI (ethyl 2,7-diamino-3,4-dicyano-5-phenylpyrazolo[1,5-a]pyridine-6-carboxylate; Naik et al. 2019 ▸), ALAFID (Wu et al. 2016 ▸), DAWKAQ {[2-(4-chlorophenyl)pyrazolo[1,5-a]pyridin-3-yl(phenyl)methanone; Ravi et al. 2017 ▸}, NADPIU [3-(4-chlorophenyl)pyrazolo[1,5-a]pyridine; Wu et al. 2016 ▸] and ZOJWAW (Barrett et al. 1996 ▸). The geometrical parameters of the –COOCH2CH3 substituent in the title compound are comparable with those reported for FIZLEI. Similarly, the geometrical parameters of the –C6H4Cl unit in the title compound are comparable with those for in DAWKAQ and NADPIU. The bond lengths of the pyrazolo[3,4-b]pyridine scaffold of the title compound are closer to those in NADPIU. The pyrazolopyridine moiety (N1–N3/C7–C9/C12–C14) of the title compound is approximately plan, as is also observed for FIZLEI, ALAFID, DAWKAQ, NADPIU and ZOJWAW. Apart from the CSD database, two other important databases, namely Drug Bank (database for FDA-approved drugs, drugs under investigation or in clinical trials, etc; Law et al. 2013 ▸) and ZINC (database for commercially available compounds; Irwin et al. 2005 ▸) were also surveyed. The former database is used for drug repurposing or drug re-profiling studies, and latter for high-throughput virtual screening against the binding site of drug target proteins to identify promising and putative inhibitors. In the Drug Bank database, there were 31 hits, based on a 0.5 similarity threshold, whereas the ZINC search gave only three hits (ZINCIDs: ZINC45166781, ZINC3852638 and ZINC39053824). Out of 31 molecules identified in the Drug Bank database, two molecules were in the approved drug category namely riciguat (accession No: DB08931, similarity score: 0.55) and teletristat ethyl (accession No: DB12095, similarity score: 0.511). The remaining 29 molecules belong to the experimental, investigational or other categories.
Synthesis and crystallization:
To a solution of 3-(4-chlorophenyl)-1-methyl-1H-pyrazol-5-amine (125 mg, 0.65 mmol) and ethyl 2-(bis(methylthio)methylene)-3-oxobutanoate (145 mg, 0.65 mmol) in toluene (5 ml) under a blanket of dry N2, a catalytic amount of trifluoroacetic acid (TFA; 30 mol%) was added. The resulting mixture was refluxed for 12 h, while monitoring progress by TLC (hexane:ethyl acetate, 99:1). After completion of the reaction, the resulting mixture was subjected to purification by column chromatography to furnish 182 mg of the title compound in 75% yield as a colourless solid, m.p. 415.85 K, R f = 0.3 (hexane:ethyl acetate 99:01). A sample suitable for single-crystal X-ray analysis was obtained by recrystallization from dry methanol.
Refinement
Crystal data, data collection and structure refinement details are summarized in Table 2 ▸. Hydrogen atoms were placed in calculated positions, with C—H = 0.93–0.97 Å and refined using a riding model with U iso(H) = 1.2 U eq(C) or 1.5 U eq(C-methyl).
Table 2. Experimental details.
| Crystal data | |
| Chemical formula | C18H18ClN3O2S |
| M r | 375.86 |
| Crystal system, space group | Monoclinic, P21/a |
| Temperature (K) | 298 |
| a, b, c (Å) | 8.9995 (5), 16.7778 (11), 12.3595 (8) |
| β (°) | 98.892 (6) |
| V (Å3) | 1843.8 (2) |
| Z | 4 |
| Radiation type | Mo Kα |
| μ (mm−1) | 0.34 |
| Crystal size (mm) | 0.65 × 0.6 × 0.24 |
| Data collection | |
| Diffractometer | Agilent Xcalibur Eos |
| Absorption correction | Multi-scan (CrysAlis PRO; Agilent, 2014 ▸) |
| T min, T max | 0.857, 1.000 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 13882, 4340, 3323 |
| R int | 0.027 |
| (sin θ/λ)max (Å−1) | 0.682 |
| Refinement | |
| R[F 2 > 2σ(F 2)], wR(F 2), S | 0.049, 0.161, 1.10 |
| No. of reflections | 4340 |
| No. of parameters | 230 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.30, −0.41 |
Supplementary Material
Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989020002479/lh5946sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989020002479/lh5946Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989020002479/lh5946Isup3.cml
CCDC reference: 1977404
Additional supporting information: crystallographic information; 3D view; checkCIF report
Acknowledgments
The authors thank the DST–FIST Single Crystal XRD facility at the Department of Chemistry, Pondicherry University, for the diffraction data and Dr Clara Gomes (FCT–UNL, Portugal) for the CSD database survey. RG thanks the Department of Chemistry for facilities, and the UGC and CSIR for a fellowship. JM thanks Dr Amit Kumar Singh (Sharda University, India) for support.
supplementary crystallographic information
Crystal data
| C18H18ClN3O2S | F(000) = 784 |
| Mr = 375.86 | Dx = 1.354 Mg m−3 |
| Monoclinic, P21/a | Mo Kα radiation, λ = 0.71073 Å |
| a = 8.9995 (5) Å | Cell parameters from 4472 reflections |
| b = 16.7778 (11) Å | θ = 3.9–29.0° |
| c = 12.3595 (8) Å | µ = 0.34 mm−1 |
| β = 98.892 (6)° | T = 298 K |
| V = 1843.8 (2) Å3 | Block, colourless |
| Z = 4 | 0.65 × 0.6 × 0.24 mm |
Data collection
| Agilent Xcalibur Eos diffractometer | 4340 independent reflections |
| Radiation source: Enhance (Mo) X-ray Source | 3323 reflections with I > 2σ(I) |
| Detector resolution: 15.9821 pixels mm-1 | Rint = 0.027 |
| ω scans | θmax = 29.0°, θmin = 3.9° |
| Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | h = −11→12 |
| Tmin = 0.857, Tmax = 1.000 | k = −22→22 |
| 13882 measured reflections | l = −15→16 |
Refinement
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.161 | H-atom parameters constrained |
| S = 1.10 | w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3 |
| 4340 reflections | (Δ/σ)max = 0.006 |
| 230 parameters | Δρmax = 0.30 e Å−3 |
| 0 restraints | Δρmin = −0.41 e Å−3 |
Special details
| Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| S1 | 0.38706 (5) | −0.06089 (3) | 0.65888 (4) | 0.04572 (19) | |
| Cl1 | −0.26383 (7) | 0.13979 (4) | 0.63284 (7) | 0.0751 (3) | |
| O1 | 0.77428 (16) | −0.12709 (8) | 0.67467 (12) | 0.0460 (4) | |
| N1 | 0.73909 (16) | 0.02099 (9) | 0.95211 (12) | 0.0363 (4) | |
| N2 | 0.57052 (18) | 0.12776 (9) | 0.97183 (14) | 0.0404 (4) | |
| O2 | 0.62392 (19) | −0.20707 (9) | 0.75585 (14) | 0.0599 (4) | |
| N3 | 0.42863 (18) | 0.15124 (10) | 0.92994 (14) | 0.0409 (4) | |
| C9 | 0.6093 (2) | 0.06010 (10) | 0.92252 (14) | 0.0335 (4) | |
| C7 | 0.37469 (19) | 0.09887 (11) | 0.85219 (15) | 0.0347 (4) | |
| C14 | 0.75435 (19) | −0.04529 (11) | 0.89531 (15) | 0.0340 (4) | |
| C3 | 0.1239 (2) | 0.04255 (12) | 0.77078 (17) | 0.0421 (5) | |
| H3 | 0.161730 | −0.008533 | 0.785668 | 0.051* | |
| C8 | 0.48642 (19) | 0.03902 (11) | 0.84112 (14) | 0.0323 (4) | |
| C15 | 0.8936 (2) | −0.09402 (12) | 0.93020 (17) | 0.0430 (5) | |
| H15A | 0.968939 | −0.061386 | 0.972304 | 0.064* | |
| H15B | 0.930807 | −0.113697 | 0.866557 | 0.064* | |
| H15C | 0.869892 | −0.138103 | 0.974026 | 0.064* | |
| C6 | 0.21737 (19) | 0.10825 (11) | 0.79948 (15) | 0.0345 (4) | |
| C12 | 0.51150 (19) | −0.02733 (11) | 0.77555 (14) | 0.0329 (4) | |
| C2 | −0.0231 (2) | 0.05183 (12) | 0.72086 (17) | 0.0435 (5) | |
| H2 | −0.083292 | 0.007504 | 0.701057 | 0.052* | |
| C5 | 0.0072 (2) | 0.19448 (12) | 0.73163 (18) | 0.0463 (5) | |
| H5 | −0.032853 | 0.245383 | 0.719599 | 0.056* | |
| C13 | 0.64421 (19) | −0.06941 (10) | 0.80566 (14) | 0.0322 (4) | |
| C4 | 0.1552 (2) | 0.18420 (12) | 0.78090 (17) | 0.0410 (4) | |
| H4 | 0.214097 | 0.228738 | 0.801982 | 0.049* | |
| C10 | 0.6609 (3) | 0.17282 (13) | 1.05805 (19) | 0.0525 (5) | |
| H10A | 0.723443 | 0.137017 | 1.105641 | 0.079* | |
| H10B | 0.596079 | 0.201357 | 1.099350 | 0.079* | |
| H10C | 0.722908 | 0.209945 | 1.026288 | 0.079* | |
| C16 | 0.6758 (2) | −0.14269 (11) | 0.74373 (15) | 0.0372 (4) | |
| C1 | −0.0800 (2) | 0.12802 (13) | 0.70063 (17) | 0.0439 (5) | |
| C11 | 0.3529 (3) | 0.02945 (16) | 0.57990 (18) | 0.0586 (6) | |
| H11A | 0.303494 | 0.067547 | 0.620089 | 0.088* | |
| H11B | 0.290191 | 0.017846 | 0.511611 | 0.088* | |
| H11C | 0.446915 | 0.051040 | 0.565940 | 0.088* | |
| C17 | 0.8220 (3) | −0.19386 (15) | 0.6139 (2) | 0.0620 (7) | |
| H17A | 0.741429 | −0.209688 | 0.556464 | 0.074* | |
| H17B | 0.847277 | −0.238963 | 0.662333 | 0.074* | |
| C18 | 0.9549 (3) | −0.16898 (19) | 0.5657 (2) | 0.0784 (9) | |
| H18A | 0.928634 | −0.124659 | 0.517341 | 0.118* | |
| H18B | 0.988342 | −0.212571 | 0.525243 | 0.118* | |
| H18C | 1.034070 | −0.153518 | 0.623018 | 0.118* |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| S1 | 0.0408 (3) | 0.0500 (3) | 0.0424 (3) | 0.0014 (2) | −0.0061 (2) | −0.0113 (2) |
| Cl1 | 0.0410 (3) | 0.0734 (5) | 0.1034 (6) | 0.0093 (3) | −0.0123 (3) | −0.0214 (4) |
| O1 | 0.0491 (8) | 0.0400 (8) | 0.0522 (8) | 0.0015 (6) | 0.0179 (7) | −0.0078 (6) |
| N1 | 0.0350 (8) | 0.0336 (8) | 0.0387 (8) | −0.0032 (6) | 0.0005 (6) | −0.0019 (7) |
| N2 | 0.0426 (9) | 0.0337 (9) | 0.0426 (9) | −0.0007 (6) | −0.0009 (7) | −0.0074 (7) |
| O2 | 0.0696 (10) | 0.0392 (9) | 0.0749 (11) | −0.0140 (7) | 0.0236 (8) | −0.0115 (8) |
| N3 | 0.0411 (9) | 0.0371 (9) | 0.0436 (9) | 0.0035 (7) | 0.0040 (7) | −0.0016 (7) |
| C9 | 0.0356 (9) | 0.0319 (9) | 0.0327 (9) | −0.0041 (7) | 0.0042 (7) | −0.0007 (7) |
| C7 | 0.0375 (9) | 0.0305 (9) | 0.0368 (9) | 0.0014 (7) | 0.0084 (7) | 0.0017 (7) |
| C14 | 0.0308 (8) | 0.0332 (9) | 0.0370 (9) | −0.0045 (7) | 0.0027 (7) | 0.0027 (8) |
| C3 | 0.0426 (10) | 0.0332 (10) | 0.0522 (12) | 0.0002 (8) | 0.0122 (9) | 0.0019 (9) |
| C8 | 0.0312 (8) | 0.0317 (9) | 0.0339 (9) | −0.0015 (7) | 0.0048 (7) | 0.0008 (7) |
| C15 | 0.0360 (9) | 0.0422 (11) | 0.0476 (11) | 0.0032 (8) | −0.0030 (8) | −0.0006 (9) |
| C6 | 0.0323 (8) | 0.0373 (10) | 0.0357 (9) | 0.0010 (7) | 0.0105 (7) | 0.0015 (8) |
| C12 | 0.0306 (8) | 0.0361 (9) | 0.0319 (9) | −0.0044 (7) | 0.0049 (7) | 0.0006 (7) |
| C2 | 0.0375 (10) | 0.0416 (11) | 0.0531 (12) | −0.0053 (8) | 0.0122 (8) | −0.0061 (9) |
| C5 | 0.0408 (10) | 0.0391 (11) | 0.0590 (13) | 0.0088 (8) | 0.0075 (9) | −0.0040 (10) |
| C13 | 0.0320 (8) | 0.0312 (9) | 0.0334 (9) | −0.0030 (7) | 0.0050 (7) | −0.0004 (7) |
| C4 | 0.0376 (9) | 0.0355 (10) | 0.0511 (11) | −0.0009 (8) | 0.0101 (8) | −0.0049 (9) |
| C10 | 0.0624 (13) | 0.0420 (12) | 0.0490 (12) | −0.0044 (10) | −0.0044 (10) | −0.0149 (10) |
| C16 | 0.0333 (9) | 0.0364 (10) | 0.0405 (10) | 0.0003 (7) | 0.0015 (7) | −0.0031 (8) |
| C1 | 0.0349 (10) | 0.0494 (12) | 0.0487 (11) | 0.0037 (8) | 0.0098 (8) | −0.0067 (9) |
| C11 | 0.0595 (13) | 0.0778 (17) | 0.0367 (10) | 0.0189 (12) | 0.0022 (9) | 0.0032 (11) |
| C17 | 0.0615 (14) | 0.0577 (15) | 0.0692 (15) | 0.0088 (11) | 0.0179 (12) | −0.0218 (12) |
| C18 | 0.0790 (19) | 0.092 (2) | 0.0719 (17) | 0.0399 (16) | 0.0366 (15) | 0.0135 (16) |
Geometric parameters (Å, º)
| S1—C12 | 1.7752 (18) | C15—H15C | 0.9600 |
| S1—C11 | 1.803 (3) | C6—C4 | 1.396 (3) |
| Cl1—C1 | 1.746 (2) | C12—C13 | 1.388 (2) |
| O1—C16 | 1.347 (2) | C2—C1 | 1.385 (3) |
| O1—C17 | 1.450 (2) | C2—H2 | 0.9300 |
| N1—C14 | 1.333 (2) | C5—C1 | 1.383 (3) |
| N1—C9 | 1.340 (2) | C5—C4 | 1.387 (3) |
| N2—C9 | 1.359 (2) | C5—H5 | 0.9300 |
| N2—N3 | 1.360 (2) | C13—C16 | 1.499 (2) |
| N2—C10 | 1.449 (2) | C4—H4 | 0.9300 |
| O2—C16 | 1.195 (2) | C10—H10A | 0.9600 |
| N3—C7 | 1.337 (2) | C10—H10B | 0.9600 |
| C9—C8 | 1.420 (2) | C10—H10C | 0.9600 |
| C7—C8 | 1.442 (2) | C11—H11A | 0.9600 |
| C7—C6 | 1.473 (2) | C11—H11B | 0.9600 |
| C14—C13 | 1.426 (2) | C11—H11C | 0.9600 |
| C14—C15 | 1.502 (3) | C17—C18 | 1.476 (3) |
| C3—C2 | 1.380 (3) | C17—H17A | 0.9700 |
| C3—C6 | 1.399 (3) | C17—H17B | 0.9700 |
| C3—H3 | 0.9300 | C18—H18A | 0.9600 |
| C8—C12 | 1.415 (2) | C18—H18B | 0.9600 |
| C15—H15A | 0.9600 | C18—H18C | 0.9600 |
| C15—H15B | 0.9600 | ||
| C12—S1—C11 | 101.91 (10) | C1—C5—H5 | 120.4 |
| C16—O1—C17 | 117.03 (16) | C4—C5—H5 | 120.4 |
| C14—N1—C9 | 114.90 (15) | C12—C13—C14 | 122.00 (17) |
| C9—N2—N3 | 111.25 (15) | C12—C13—C16 | 120.27 (16) |
| C9—N2—C10 | 127.70 (17) | C14—C13—C16 | 117.74 (16) |
| N3—N2—C10 | 121.05 (16) | C5—C4—C6 | 121.27 (18) |
| C7—N3—N2 | 107.38 (15) | C5—C4—H4 | 119.4 |
| N1—C9—N2 | 124.05 (17) | C6—C4—H4 | 119.4 |
| N1—C9—C8 | 128.45 (16) | N2—C10—H10A | 109.5 |
| N2—C9—C8 | 107.43 (16) | N2—C10—H10B | 109.5 |
| N3—C7—C8 | 110.17 (16) | H10A—C10—H10B | 109.5 |
| N3—C7—C6 | 117.73 (15) | N2—C10—H10C | 109.5 |
| C8—C7—C6 | 131.99 (16) | H10A—C10—H10C | 109.5 |
| N1—C14—C13 | 121.99 (16) | H10B—C10—H10C | 109.5 |
| N1—C14—C15 | 116.87 (16) | O2—C16—O1 | 124.26 (18) |
| C13—C14—C15 | 121.14 (17) | O2—C16—C13 | 124.64 (17) |
| C2—C3—C6 | 121.48 (19) | O1—C16—C13 | 111.07 (15) |
| C2—C3—H3 | 119.3 | C5—C1—C2 | 121.04 (19) |
| C6—C3—H3 | 119.3 | C5—C1—Cl1 | 119.79 (16) |
| C12—C8—C9 | 115.20 (15) | C2—C1—Cl1 | 119.16 (16) |
| C12—C8—C7 | 140.99 (16) | S1—C11—H11A | 109.5 |
| C9—C8—C7 | 103.74 (15) | S1—C11—H11B | 109.5 |
| C14—C15—H15A | 109.5 | H11A—C11—H11B | 109.5 |
| C14—C15—H15B | 109.5 | S1—C11—H11C | 109.5 |
| H15A—C15—H15B | 109.5 | H11A—C11—H11C | 109.5 |
| C14—C15—H15C | 109.5 | H11B—C11—H11C | 109.5 |
| H15A—C15—H15C | 109.5 | O1—C17—C18 | 108.3 (2) |
| H15B—C15—H15C | 109.5 | O1—C17—H17A | 110.0 |
| C4—C6—C3 | 117.87 (17) | C18—C17—H17A | 110.0 |
| C4—C6—C7 | 120.25 (17) | O1—C17—H17B | 110.0 |
| C3—C6—C7 | 121.83 (17) | C18—C17—H17B | 110.0 |
| C13—C12—C8 | 116.96 (16) | H17A—C17—H17B | 108.4 |
| C13—C12—S1 | 117.71 (14) | C17—C18—H18A | 109.5 |
| C8—C12—S1 | 125.32 (13) | C17—C18—H18B | 109.5 |
| C3—C2—C1 | 119.14 (19) | H18A—C18—H18B | 109.5 |
| C3—C2—H2 | 120.4 | C17—C18—H18C | 109.5 |
| C1—C2—H2 | 120.4 | H18A—C18—H18C | 109.5 |
| C1—C5—C4 | 119.13 (19) | H18B—C18—H18C | 109.5 |
| C9—N2—N3—C7 | −0.4 (2) | C9—C8—C12—S1 | −173.01 (13) |
| C10—N2—N3—C7 | 179.58 (18) | C7—C8—C12—S1 | 3.2 (3) |
| C14—N1—C9—N2 | 178.40 (16) | C11—S1—C12—C13 | −128.93 (15) |
| C14—N1—C9—C8 | 1.6 (3) | C11—S1—C12—C8 | 51.29 (17) |
| N3—N2—C9—N1 | −175.78 (16) | C6—C3—C2—C1 | −1.2 (3) |
| C10—N2—C9—N1 | 4.2 (3) | C8—C12—C13—C14 | −2.9 (3) |
| N3—N2—C9—C8 | 1.6 (2) | S1—C12—C13—C14 | 177.35 (13) |
| C10—N2—C9—C8 | −178.42 (19) | C8—C12—C13—C16 | 177.08 (15) |
| N2—N3—C7—C8 | −0.9 (2) | S1—C12—C13—C16 | −2.7 (2) |
| N2—N3—C7—C6 | 175.72 (15) | N1—C14—C13—C12 | −3.1 (3) |
| C9—N1—C14—C13 | 3.7 (2) | C15—C14—C13—C12 | 176.81 (16) |
| C9—N1—C14—C15 | −176.20 (16) | N1—C14—C13—C16 | 177.00 (15) |
| N1—C9—C8—C12 | −7.2 (3) | C15—C14—C13—C16 | −3.1 (3) |
| N2—C9—C8—C12 | 175.55 (15) | C1—C5—C4—C6 | 0.1 (3) |
| N1—C9—C8—C7 | 175.22 (17) | C3—C6—C4—C5 | −2.5 (3) |
| N2—C9—C8—C7 | −2.00 (19) | C7—C6—C4—C5 | −179.85 (17) |
| N3—C7—C8—C12 | −174.7 (2) | C17—O1—C16—O2 | −1.7 (3) |
| C6—C7—C8—C12 | 9.4 (4) | C17—O1—C16—C13 | 176.52 (18) |
| N3—C7—C8—C9 | 1.81 (19) | C12—C13—C16—O2 | −79.4 (3) |
| C6—C7—C8—C9 | −174.18 (18) | C14—C13—C16—O2 | 100.5 (2) |
| C2—C3—C6—C4 | 3.1 (3) | C12—C13—C16—O1 | 102.39 (19) |
| C2—C3—C6—C7 | −179.64 (17) | C14—C13—C16—O1 | −77.7 (2) |
| N3—C7—C6—C4 | 35.3 (2) | C4—C5—C1—C2 | 1.8 (3) |
| C8—C7—C6—C4 | −148.98 (19) | C4—C5—C1—Cl1 | −177.07 (15) |
| N3—C7—C6—C3 | −141.96 (19) | C3—C2—C1—C5 | −1.3 (3) |
| C8—C7—C6—C3 | 33.8 (3) | C3—C2—C1—Cl1 | 177.61 (15) |
| C9—C8—C12—C13 | 7.2 (2) | C16—O1—C17—C18 | −166.05 (19) |
| C7—C8—C12—C13 | −176.6 (2) |
Hydrogen-bond geometry (Å, º)
| D—H···A | D—H | H···A | D···A | D—H···A |
| C2—H2···O1i | 0.93 | 2.59 | 3.513 (2) | 170 |
Symmetry code: (i) x−1, 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/S2056989020002479/lh5946sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989020002479/lh5946Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989020002479/lh5946Isup3.cml
CCDC reference: 1977404
Additional supporting information: crystallographic information; 3D view; checkCIF report