organic compounds
4-(4-Bromophenyl)-2-(3-(4-chlorophenyl)-5-{3-[5-methyl-1-(4-methylphenyl)-1H-1,2,3-triazol-4-yl]-1-phenyl-1H-pyrazol-4-yl}-4,5-dihydro-1H-pyrazol-1-yl)-1,3-thiazole
aCornea Research Chair, Department of Optometry, College of Applied Medical Sciences, King Saud University, PO Box 10219, Riyadh 11433, Saudi Arabia, bDepartment of Chemistry, College of Science and Humanities, Shaqra University, Duwadimi, Saudi Arabia, cApplied Organic Chemistry Department, National Research Centre, Dokki 12622, Giza, Egypt, dChemistry Department, Faculty of Science, Jazan University, Jazan 2079, Saudi Arabia, eChemical Industries Division, National Research Centre, Dokki 12622, Giza, Egypt, fChemistry Department, Faculty of Science, Damietta University, Egypt, and gSchool of Chemistry, Cardiff University, Main Building, Park Place, Cardiff CF10 3AT, UK
*Correspondence e-mail: gelhiti@ksu.edu.sa
The 37H28BrClN8S, comprises one molecule. The molecule consists of two ring systems joined by a C—C bond between the dihydropyrazolyl and pyrazolyl rings of the two extended ring systems. The angles between adjacent ring planes of the tolyl–triazolyl–pyrazolyl–phenyl ring system are 48.2 (1), 12.3 (2) and 22.2 (2)°, respectively, with angles of 19.7 (1), 5.6 (2) and 0.9 (2)° between the rings of the chlorophenyl–thiazolyl–dihydropyrazolyl–bromophenyl set. The pyrazolyl and dihydropyrazolyl rings are inclined at 68.3 (1)° to one another. In the crystal, C—H⋯Cl interactions form chains of molecules parallel to the b-axis direction.
of the title compound, CKeywords: crystal structure; thiazole; pyrazole; 2.2.3-triazole.
CCDC reference: 1830297
Structure description
Various efficient procedures have been reported for the synthesis of pyrazole (Panda & Jena, 2012; Wu et al., 2012) and triazine ring systems (Oudir et al., 2006; Shie & Fang, 2007). Heterocycles containing such moieties show biological activities (Abd El-All et al., 2015; Ansari et al., 2017; El-Barbary et al., 2005). The X-ray of a related compound, (E)-1-[5-methyl-1-(p-tolyl)-1H-1,2,3-triazol-4-yl]-3-{3-[5-methyl-1-(p-tolyl)-1H-1,2,3-triazol-4-yl]-1-phenyl-1H-pyrazol-4-yl}prop-2-en-1-one has been published recently (Abu El-Enin et al., 2017).
The 37H28BrClN8S (Fig. 1). The molecule consists of two ring systems joined by the C12—C19 bond. The angles between the planes of the tolyl–triazolyl–pyrazolyl–phenyl rings are 48.2 (1), 12.3 (2) and 22.2 (2)°, while those between the planes of the chlorophenyl–thiazolyl–dihydropyrazolyl–bromophenyl rings are 19.7 (1), 5.6 (2) and 0.9 (2)°, respectively. The planes of the pyrazolyl and dihydropyrazolyl rings are inclined at 68.3 (1)°. In the crystal, C5—H5⋯Cl1 hydrogen bonds form zigzag chains of molecules parallel to the b-axis direction (Fig. 2, Table 1).
comprises one molecule of CSynthesis and crystallization
The title compound was synthesized based on a literature procedure (Abdel-Wahab et al., 2017) by the reaction of a mixture of equimolar quantities of 3-(4-chlorophenyl)-5-(3-(5-methyl-1-(4-methylphenyl)-1H-1,2,3-triazol-4-yl)-1-phenyl-1H-pyrazol-4-yl)-4,5-dihydro-1H-pyrazole-1-carbothioamide and 2-bromo-1-phenylethanone in refluxing dry ethanol for 2 h. The solid obtained on cooling was collected by filtration, washed with ethanol, dried and recrystallized from dimethylformamide to give yellow crystals (83%), m.p. 279–281°C (lit. m.p. 279–281°C; Abdel-Wahab et al., 2017). The spectroscopic data for the title compound are consistent with those reported (Abdel-Wahab et al., 2017).
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1830297
https://doi.org/10.1107/S2414314618004431/sj4169sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314618004431/sj4169Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314618004431/sj4169Isup3.cml
Data collection: CrysAlis PRO (Rigaku OD, 2015); cell
CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and CHEMDRAW Ultra (Cambridge Soft, 2001).C37H28BrClN8S | F(000) = 1496 |
Mr = 732.09 | Dx = 1.454 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54184 Å |
a = 10.4422 (3) Å | Cell parameters from 9285 reflections |
b = 13.3065 (3) Å | θ = 3.7–74.2° |
c = 24.0683 (8) Å | µ = 3.32 mm−1 |
β = 90.181 (3)° | T = 296 K |
V = 3344.25 (17) Å3 | Needle, yellow |
Z = 4 | 0.49 × 0.09 × 0.05 mm |
Rigaku Oxford Diffraction SuperNova, Dual, Cu at zero, Atlas diffractometer | 5579 reflections with I > 2σ(I) |
ω scans | Rint = 0.034 |
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2015) | θmax = 74.3°, θmin = 3.7° |
Tmin = 0.949, Tmax = 0.992 | h = −9→13 |
23807 measured reflections | k = −16→16 |
6739 independent reflections | l = −29→28 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.047 | H-atom parameters constrained |
wR(F2) = 0.138 | w = 1/[σ2(Fo2) + (0.065P)2 + 1.9503P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
6739 reflections | Δρmax = 0.77 e Å−3 |
435 parameters | Δρmin = −1.04 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.2922 (3) | 1.1211 (2) | 0.21922 (13) | 0.0619 (7) | |
C2 | 0.3757 (3) | 1.1642 (2) | 0.18276 (14) | 0.0612 (7) | |
H2 | 0.369306 | 1.232184 | 0.174323 | 0.073* | |
C3 | 0.4700 (3) | 1.1059 (2) | 0.15841 (13) | 0.0558 (6) | |
H3 | 0.526327 | 1.134866 | 0.133223 | 0.067* | |
C4 | 0.4811 (2) | 1.00435 (19) | 0.17131 (10) | 0.0464 (5) | |
C5 | 0.3936 (3) | 0.9633 (2) | 0.20794 (12) | 0.0567 (6) | |
H5 | 0.399123 | 0.895383 | 0.216661 | 0.068* | |
C6 | 0.2986 (3) | 1.0204 (2) | 0.23182 (14) | 0.0660 (8) | |
H6 | 0.239932 | 0.991458 | 0.256005 | 0.079* | |
C7 | 0.5829 (2) | 0.94164 (18) | 0.14708 (10) | 0.0458 (5) | |
C8 | 0.6520 (3) | 0.9630 (2) | 0.10122 (11) | 0.0552 (6) | |
H8 | 0.641481 | 1.020598 | 0.079785 | 0.066* | |
C9 | 0.7074 (2) | 0.80843 (18) | 0.14708 (10) | 0.0453 (5) | |
C10 | 0.8801 (2) | 0.58992 (18) | 0.15202 (10) | 0.0438 (5) | |
C11 | 0.8067 (3) | 0.56615 (19) | 0.20398 (11) | 0.0515 (6) | |
H11A | 0.863850 | 0.556163 | 0.235335 | 0.062* | |
H11B | 0.754168 | 0.506626 | 0.199149 | 0.062* | |
C12 | 0.7233 (2) | 0.66059 (18) | 0.21193 (9) | 0.0450 (5) | |
H12 | 0.632306 | 0.643696 | 0.208392 | 0.054* | |
C13 | 0.9737 (2) | 0.52266 (19) | 0.12667 (10) | 0.0465 (5) | |
C14 | 1.0370 (3) | 0.5501 (2) | 0.07788 (13) | 0.0626 (7) | |
H14 | 1.020128 | 0.612167 | 0.061638 | 0.075* | |
C15 | 1.1241 (3) | 0.4862 (2) | 0.05370 (14) | 0.0696 (8) | |
H15 | 1.165783 | 0.504754 | 0.021184 | 0.084* | |
C16 | 1.1491 (3) | 0.3944 (2) | 0.07801 (13) | 0.0590 (7) | |
C17 | 1.0884 (3) | 0.3645 (2) | 0.12567 (13) | 0.0615 (7) | |
H17 | 1.105771 | 0.302244 | 0.141528 | 0.074* | |
C18 | 1.0001 (3) | 0.4295 (2) | 0.14975 (11) | 0.0556 (6) | |
H18 | 0.957969 | 0.410073 | 0.181989 | 0.067* | |
C19 | 0.7488 (2) | 0.71190 (17) | 0.26631 (9) | 0.0410 (5) | |
C20 | 0.8273 (2) | 0.79145 (17) | 0.27590 (9) | 0.0427 (5) | |
H20 | 0.872623 | 0.827373 | 0.249274 | 0.051* | |
C21 | 0.7027 (2) | 0.68410 (17) | 0.31975 (10) | 0.0416 (5) | |
C22 | 0.8922 (2) | 0.88705 (18) | 0.36012 (10) | 0.0445 (5) | |
C23 | 0.9970 (3) | 0.9333 (2) | 0.33606 (11) | 0.0555 (6) | |
H23 | 1.027775 | 0.911261 | 0.301957 | 0.067* | |
C24 | 1.0554 (3) | 1.0124 (2) | 0.36307 (14) | 0.0705 (8) | |
H24 | 1.125462 | 1.044056 | 0.346990 | 0.085* | |
C25 | 1.0108 (4) | 1.0445 (3) | 0.41342 (16) | 0.0832 (10) | |
H25 | 1.050677 | 1.097814 | 0.431482 | 0.100* | |
C26 | 0.9069 (4) | 0.9979 (3) | 0.43743 (15) | 0.0786 (10) | |
H26 | 0.876911 | 1.020124 | 0.471628 | 0.094* | |
C27 | 0.8470 (3) | 0.9186 (2) | 0.41125 (12) | 0.0589 (7) | |
H27 | 0.777388 | 0.886771 | 0.427646 | 0.071* | |
C28 | 0.6135 (2) | 0.60317 (18) | 0.33277 (10) | 0.0435 (5) | |
C29 | 0.5439 (2) | 0.58454 (17) | 0.38029 (10) | 0.0425 (5) | |
C30 | 0.5483 (3) | 0.6320 (2) | 0.43635 (10) | 0.0547 (6) | |
H30A | 0.475266 | 0.674961 | 0.440903 | 0.082* | |
H30B | 0.625283 | 0.670933 | 0.439922 | 0.082* | |
H30C | 0.547254 | 0.580589 | 0.464343 | 0.082* | |
C31 | 0.3757 (2) | 0.45259 (18) | 0.39841 (10) | 0.0441 (5) | |
C32 | 0.2830 (2) | 0.50835 (18) | 0.42458 (10) | 0.0474 (5) | |
H32 | 0.284781 | 0.578157 | 0.422796 | 0.057* | |
C33 | 0.1872 (2) | 0.4598 (2) | 0.45361 (11) | 0.0493 (5) | |
H33 | 0.125172 | 0.497936 | 0.471547 | 0.059* | |
C34 | 0.1808 (2) | 0.3566 (2) | 0.45674 (11) | 0.0500 (6) | |
C35 | 0.2747 (3) | 0.3022 (2) | 0.42921 (14) | 0.0627 (7) | |
H35 | 0.271692 | 0.232421 | 0.430176 | 0.075* | |
C36 | 0.3726 (3) | 0.3487 (2) | 0.40040 (14) | 0.0604 (7) | |
H36 | 0.435162 | 0.310790 | 0.382691 | 0.072* | |
C37 | 0.0747 (3) | 0.3056 (2) | 0.48799 (15) | 0.0703 (8) | |
H37A | 0.007207 | 0.287989 | 0.462655 | 0.105* | |
H37B | 0.042087 | 0.350380 | 0.515841 | 0.105* | |
H37C | 0.107183 | 0.245922 | 0.505456 | 0.105* | |
N1 | 0.6142 (2) | 0.85150 (15) | 0.17330 (8) | 0.0461 (4) | |
N2 | 0.7650 (2) | 0.72265 (16) | 0.16456 (9) | 0.0504 (5) | |
N3 | 0.8545 (2) | 0.67696 (16) | 0.13134 (8) | 0.0468 (4) | |
N4 | 0.8275 (2) | 0.80893 (14) | 0.33154 (8) | 0.0433 (4) | |
N5 | 0.75076 (19) | 0.74371 (15) | 0.35922 (8) | 0.0443 (4) | |
N6 | 0.5845 (2) | 0.53162 (17) | 0.29427 (9) | 0.0522 (5) | |
N7 | 0.4991 (2) | 0.47018 (17) | 0.31457 (9) | 0.0536 (5) | |
N8 | 0.47323 (19) | 0.50237 (15) | 0.36707 (8) | 0.0453 (4) | |
Cl1 | 0.17330 (11) | 1.19476 (7) | 0.25039 (5) | 0.0961 (3) | |
S1 | 0.76202 (6) | 0.86975 (5) | 0.08757 (3) | 0.05486 (18) | |
Br1 | 1.26903 (4) | 0.30625 (3) | 0.04415 (2) | 0.08860 (17) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0619 (16) | 0.0500 (15) | 0.0737 (18) | 0.0087 (12) | 0.0066 (14) | −0.0036 (13) |
C2 | 0.0657 (17) | 0.0354 (12) | 0.083 (2) | 0.0016 (12) | 0.0036 (14) | 0.0015 (12) |
C3 | 0.0552 (14) | 0.0433 (13) | 0.0691 (17) | −0.0054 (11) | 0.0038 (12) | 0.0064 (12) |
C4 | 0.0452 (12) | 0.0429 (12) | 0.0510 (13) | −0.0020 (10) | −0.0021 (10) | 0.0009 (10) |
C5 | 0.0623 (15) | 0.0407 (13) | 0.0672 (16) | 0.0030 (11) | 0.0114 (13) | 0.0078 (12) |
C6 | 0.0705 (18) | 0.0552 (16) | 0.0724 (18) | 0.0061 (14) | 0.0232 (15) | 0.0111 (14) |
C7 | 0.0467 (12) | 0.0412 (12) | 0.0494 (12) | −0.0016 (10) | −0.0015 (10) | 0.0012 (10) |
C8 | 0.0568 (14) | 0.0532 (15) | 0.0556 (14) | 0.0047 (12) | 0.0062 (11) | 0.0125 (12) |
C9 | 0.0513 (13) | 0.0435 (12) | 0.0412 (11) | −0.0003 (10) | 0.0021 (10) | −0.0023 (9) |
C10 | 0.0475 (12) | 0.0399 (12) | 0.0440 (12) | −0.0023 (9) | 0.0046 (9) | −0.0036 (9) |
C11 | 0.0688 (16) | 0.0384 (12) | 0.0475 (13) | 0.0005 (11) | 0.0139 (11) | −0.0035 (10) |
C12 | 0.0523 (13) | 0.0412 (12) | 0.0416 (12) | −0.0014 (10) | 0.0083 (10) | −0.0024 (9) |
C13 | 0.0464 (12) | 0.0433 (12) | 0.0498 (13) | −0.0011 (10) | 0.0064 (10) | −0.0044 (10) |
C14 | 0.0671 (17) | 0.0491 (15) | 0.0716 (18) | 0.0078 (13) | 0.0241 (14) | 0.0082 (13) |
C15 | 0.0724 (19) | 0.0587 (17) | 0.078 (2) | 0.0071 (14) | 0.0353 (16) | 0.0085 (15) |
C16 | 0.0582 (15) | 0.0461 (14) | 0.0728 (18) | 0.0045 (12) | 0.0136 (13) | −0.0061 (12) |
C17 | 0.0785 (19) | 0.0419 (13) | 0.0642 (17) | 0.0072 (13) | 0.0113 (14) | 0.0009 (12) |
C18 | 0.0691 (16) | 0.0445 (13) | 0.0533 (14) | 0.0013 (12) | 0.0131 (12) | 0.0009 (11) |
C19 | 0.0461 (11) | 0.0360 (11) | 0.0411 (11) | 0.0010 (9) | 0.0078 (9) | −0.0024 (9) |
C20 | 0.0514 (12) | 0.0387 (11) | 0.0381 (11) | −0.0014 (9) | 0.0085 (9) | 0.0003 (9) |
C21 | 0.0447 (11) | 0.0369 (11) | 0.0433 (11) | 0.0009 (9) | 0.0101 (9) | −0.0012 (9) |
C22 | 0.0520 (13) | 0.0375 (11) | 0.0440 (12) | 0.0015 (10) | 0.0004 (10) | −0.0030 (9) |
C23 | 0.0664 (16) | 0.0481 (14) | 0.0520 (14) | −0.0115 (12) | 0.0054 (12) | −0.0008 (11) |
C24 | 0.081 (2) | 0.0608 (18) | 0.0693 (19) | −0.0235 (16) | 0.0040 (15) | −0.0008 (14) |
C25 | 0.094 (2) | 0.068 (2) | 0.087 (2) | −0.0258 (19) | −0.0005 (19) | −0.0274 (18) |
C26 | 0.083 (2) | 0.085 (2) | 0.0681 (19) | −0.0104 (18) | 0.0112 (16) | −0.0351 (17) |
C27 | 0.0592 (15) | 0.0628 (17) | 0.0547 (15) | −0.0047 (13) | 0.0075 (12) | −0.0134 (13) |
C28 | 0.0459 (12) | 0.0405 (11) | 0.0440 (12) | −0.0009 (9) | 0.0082 (9) | −0.0023 (9) |
C29 | 0.0428 (11) | 0.0400 (11) | 0.0449 (12) | −0.0015 (9) | 0.0069 (9) | 0.0000 (9) |
C30 | 0.0606 (15) | 0.0587 (15) | 0.0450 (13) | −0.0109 (12) | 0.0078 (11) | −0.0034 (11) |
C31 | 0.0434 (12) | 0.0421 (12) | 0.0468 (12) | −0.0043 (9) | 0.0063 (9) | 0.0002 (10) |
C32 | 0.0517 (13) | 0.0373 (11) | 0.0531 (13) | 0.0000 (10) | 0.0082 (10) | 0.0036 (10) |
C33 | 0.0466 (12) | 0.0479 (13) | 0.0534 (13) | 0.0023 (10) | 0.0112 (10) | −0.0006 (10) |
C34 | 0.0469 (12) | 0.0463 (13) | 0.0567 (14) | −0.0050 (10) | 0.0055 (10) | 0.0023 (11) |
C35 | 0.0606 (16) | 0.0371 (13) | 0.091 (2) | −0.0047 (11) | 0.0197 (15) | −0.0009 (13) |
C36 | 0.0554 (15) | 0.0417 (13) | 0.084 (2) | −0.0008 (11) | 0.0233 (14) | −0.0084 (13) |
C37 | 0.0640 (18) | 0.0562 (17) | 0.091 (2) | −0.0112 (13) | 0.0252 (16) | 0.0063 (15) |
N1 | 0.0499 (11) | 0.0430 (10) | 0.0455 (10) | 0.0022 (9) | 0.0051 (8) | 0.0028 (8) |
N2 | 0.0616 (12) | 0.0456 (11) | 0.0441 (10) | 0.0101 (9) | 0.0126 (9) | 0.0028 (9) |
N3 | 0.0491 (11) | 0.0475 (11) | 0.0440 (10) | 0.0032 (9) | 0.0098 (8) | 0.0001 (8) |
N4 | 0.0515 (11) | 0.0358 (10) | 0.0426 (10) | −0.0034 (8) | 0.0086 (8) | −0.0019 (7) |
N5 | 0.0495 (10) | 0.0406 (10) | 0.0429 (10) | −0.0037 (8) | 0.0103 (8) | −0.0016 (8) |
N6 | 0.0566 (12) | 0.0490 (12) | 0.0512 (11) | −0.0091 (9) | 0.0163 (9) | −0.0078 (9) |
N7 | 0.0583 (12) | 0.0495 (12) | 0.0531 (12) | −0.0103 (10) | 0.0159 (10) | −0.0101 (9) |
N8 | 0.0462 (10) | 0.0427 (10) | 0.0471 (11) | −0.0057 (8) | 0.0100 (8) | −0.0026 (8) |
Cl1 | 0.1044 (7) | 0.0663 (5) | 0.1178 (8) | 0.0307 (5) | 0.0396 (6) | 0.0029 (5) |
S1 | 0.0563 (4) | 0.0581 (4) | 0.0502 (3) | 0.0051 (3) | 0.0110 (3) | 0.0087 (3) |
Br1 | 0.0960 (3) | 0.0521 (2) | 0.1181 (3) | 0.01555 (17) | 0.0517 (2) | −0.00092 (18) |
C1—C2 | 1.365 (4) | C20—H20 | 0.9300 |
C1—C6 | 1.376 (4) | C21—N5 | 1.334 (3) |
C1—Cl1 | 1.752 (3) | C21—C28 | 1.459 (3) |
C2—C3 | 1.385 (4) | C22—C27 | 1.384 (4) |
C2—H2 | 0.9300 | C22—C23 | 1.385 (4) |
C3—C4 | 1.391 (4) | C22—N4 | 1.417 (3) |
C3—H3 | 0.9300 | C23—C24 | 1.377 (4) |
C4—C5 | 1.384 (4) | C23—H23 | 0.9300 |
C4—C7 | 1.474 (3) | C24—C25 | 1.368 (5) |
C5—C6 | 1.376 (4) | C24—H24 | 0.9300 |
C5—H5 | 0.9300 | C25—C26 | 1.379 (5) |
C6—H6 | 0.9300 | C25—H25 | 0.9300 |
C7—C8 | 1.350 (4) | C26—C27 | 1.378 (4) |
C7—N1 | 1.394 (3) | C26—H26 | 0.9300 |
C8—S1 | 1.724 (3) | C27—H27 | 0.9300 |
C8—H8 | 0.9300 | C28—N6 | 1.362 (3) |
C9—N1 | 1.295 (3) | C28—C29 | 1.380 (3) |
C9—N2 | 1.357 (3) | C29—N8 | 1.356 (3) |
C9—S1 | 1.746 (2) | C29—C30 | 1.490 (3) |
C10—N3 | 1.288 (3) | C30—H30A | 0.9600 |
C10—C13 | 1.460 (3) | C30—H30B | 0.9600 |
C10—C11 | 1.503 (3) | C30—H30C | 0.9600 |
C11—C12 | 1.541 (3) | C31—C32 | 1.374 (3) |
C11—H11A | 0.9700 | C31—C36 | 1.384 (4) |
C11—H11B | 0.9700 | C31—N8 | 1.431 (3) |
C12—N2 | 1.475 (3) | C32—C33 | 1.383 (3) |
C12—C19 | 1.499 (3) | C32—H32 | 0.9300 |
C12—H12 | 0.9800 | C33—C34 | 1.376 (4) |
C13—C18 | 1.385 (4) | C33—H33 | 0.9300 |
C13—C14 | 1.398 (4) | C34—C35 | 1.389 (4) |
C14—C15 | 1.376 (4) | C34—C37 | 1.502 (4) |
C14—H14 | 0.9300 | C35—C36 | 1.383 (4) |
C15—C16 | 1.379 (4) | C35—H35 | 0.9300 |
C15—H15 | 0.9300 | C36—H36 | 0.9300 |
C16—C17 | 1.371 (4) | C37—H37A | 0.9600 |
C16—Br1 | 1.902 (3) | C37—H37B | 0.9600 |
C17—C18 | 1.392 (4) | C37—H37C | 0.9600 |
C17—H17 | 0.9300 | N2—N3 | 1.374 (3) |
C18—H18 | 0.9300 | N4—N5 | 1.357 (3) |
C19—C20 | 1.358 (3) | N6—N7 | 1.306 (3) |
C19—C21 | 1.424 (3) | N7—N8 | 1.362 (3) |
C20—N4 | 1.359 (3) | ||
C2—C1—C6 | 121.3 (3) | C27—C22—C23 | 120.6 (2) |
C2—C1—Cl1 | 119.7 (2) | C27—C22—N4 | 119.4 (2) |
C6—C1—Cl1 | 119.0 (2) | C23—C22—N4 | 120.0 (2) |
C1—C2—C3 | 119.6 (3) | C24—C23—C22 | 119.4 (3) |
C1—C2—H2 | 120.2 | C24—C23—H23 | 120.3 |
C3—C2—H2 | 120.2 | C22—C23—H23 | 120.3 |
C2—C3—C4 | 120.6 (3) | C25—C24—C23 | 120.3 (3) |
C2—C3—H3 | 119.7 | C25—C24—H24 | 119.8 |
C4—C3—H3 | 119.7 | C23—C24—H24 | 119.8 |
C5—C4—C3 | 118.1 (2) | C24—C25—C26 | 120.1 (3) |
C5—C4—C7 | 120.5 (2) | C24—C25—H25 | 120.0 |
C3—C4—C7 | 121.4 (2) | C26—C25—H25 | 120.0 |
C6—C5—C4 | 121.8 (3) | C27—C26—C25 | 120.6 (3) |
C6—C5—H5 | 119.1 | C27—C26—H26 | 119.7 |
C4—C5—H5 | 119.1 | C25—C26—H26 | 119.7 |
C1—C6—C5 | 118.7 (3) | C26—C27—C22 | 118.9 (3) |
C1—C6—H6 | 120.6 | C26—C27—H27 | 120.6 |
C5—C6—H6 | 120.6 | C22—C27—H27 | 120.6 |
C8—C7—N1 | 115.2 (2) | N6—C28—C29 | 108.8 (2) |
C8—C7—C4 | 126.3 (2) | N6—C28—C21 | 120.7 (2) |
N1—C7—C4 | 118.5 (2) | C29—C28—C21 | 130.5 (2) |
C7—C8—S1 | 111.2 (2) | N8—C29—C28 | 103.8 (2) |
C7—C8—H8 | 124.4 | N8—C29—C30 | 124.7 (2) |
S1—C8—H8 | 124.4 | C28—C29—C30 | 131.3 (2) |
N1—C9—N2 | 123.7 (2) | C29—C30—H30A | 109.5 |
N1—C9—S1 | 116.16 (18) | C29—C30—H30B | 109.5 |
N2—C9—S1 | 120.11 (19) | H30A—C30—H30B | 109.5 |
N3—C10—C13 | 121.8 (2) | C29—C30—H30C | 109.5 |
N3—C10—C11 | 113.9 (2) | H30A—C30—H30C | 109.5 |
C13—C10—C11 | 124.2 (2) | H30B—C30—H30C | 109.5 |
C10—C11—C12 | 102.8 (2) | C32—C31—C36 | 120.5 (2) |
C10—C11—H11A | 111.2 | C32—C31—N8 | 119.7 (2) |
C12—C11—H11A | 111.2 | C36—C31—N8 | 119.8 (2) |
C10—C11—H11B | 111.2 | C31—C32—C33 | 119.4 (2) |
C12—C11—H11B | 111.2 | C31—C32—H32 | 120.3 |
H11A—C11—H11B | 109.1 | C33—C32—H32 | 120.3 |
N2—C12—C19 | 111.6 (2) | C34—C33—C32 | 121.9 (2) |
N2—C12—C11 | 101.09 (18) | C34—C33—H33 | 119.0 |
C19—C12—C11 | 112.4 (2) | C32—C33—H33 | 119.0 |
N2—C12—H12 | 110.5 | C33—C34—C35 | 117.3 (2) |
C19—C12—H12 | 110.5 | C33—C34—C37 | 120.9 (2) |
C11—C12—H12 | 110.5 | C35—C34—C37 | 121.8 (2) |
C18—C13—C14 | 118.5 (2) | C36—C35—C34 | 122.1 (2) |
C18—C13—C10 | 120.9 (2) | C36—C35—H35 | 119.0 |
C14—C13—C10 | 120.6 (2) | C34—C35—H35 | 119.0 |
C15—C14—C13 | 120.6 (3) | C35—C36—C31 | 118.8 (2) |
C15—C14—H14 | 119.7 | C35—C36—H36 | 120.6 |
C13—C14—H14 | 119.7 | C31—C36—H36 | 120.6 |
C14—C15—C16 | 119.5 (3) | C34—C37—H37A | 109.5 |
C14—C15—H15 | 120.2 | C34—C37—H37B | 109.5 |
C16—C15—H15 | 120.2 | H37A—C37—H37B | 109.5 |
C17—C16—C15 | 121.6 (3) | C34—C37—H37C | 109.5 |
C17—C16—Br1 | 119.1 (2) | H37A—C37—H37C | 109.5 |
C15—C16—Br1 | 119.2 (2) | H37B—C37—H37C | 109.5 |
C16—C17—C18 | 118.4 (3) | C9—N1—C7 | 109.6 (2) |
C16—C17—H17 | 120.8 | C9—N2—N3 | 119.6 (2) |
C18—C17—H17 | 120.8 | C9—N2—C12 | 125.4 (2) |
C13—C18—C17 | 121.4 (3) | N3—N2—C12 | 113.92 (19) |
C13—C18—H18 | 119.3 | C10—N3—N2 | 108.3 (2) |
C17—C18—H18 | 119.3 | N5—N4—C20 | 112.04 (19) |
C20—C19—C21 | 104.8 (2) | N5—N4—C22 | 120.81 (19) |
C20—C19—C12 | 127.5 (2) | C20—N4—C22 | 127.1 (2) |
C21—C19—C12 | 127.6 (2) | C21—N5—N4 | 104.58 (18) |
C19—C20—N4 | 107.4 (2) | N7—N6—C28 | 109.5 (2) |
C19—C20—H20 | 126.3 | N6—N7—N8 | 106.73 (19) |
N4—C20—H20 | 126.3 | C29—N8—N7 | 111.21 (19) |
N5—C21—C19 | 111.2 (2) | C29—N8—C31 | 129.6 (2) |
N5—C21—C28 | 121.7 (2) | N7—N8—C31 | 119.12 (19) |
C19—C21—C28 | 127.2 (2) | C8—S1—C9 | 87.72 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···Cl1i | 0.93 | 2.89 | 3.778 (3) | 161 |
Symmetry code: (i) −x+1/2, y−1/2, −z+1/2. |
Footnotes
‡Additional corresponding author, e-mail: kariukib@cardiff.ac.uk.
Funding information
This project was supported by King Saud University, Deanship of Scientific Research, Research Chairs.
References
Abd El-All, A. S., Osman, S. A., Roaiah, H. M. F., Abdalla, M. M., Abd El Aty, A. A. & AbdEl-Hady, W. H. (2015). Med. Chem. Res. 24, 4093–4104. CAS Google Scholar
Abdel-Wahab, B. F., Khidre, R. E., Mohamed, H. A. & El-Hiti, G. A. (2017). Arab. J. Sci. Eng. 42, 2441–2448. CAS Google Scholar
Abu El-Enin, M. A. B., Abdel-Wahab, B. F., Baashen, M., Ghabbour, H. A. & El-Hiti, G. A. (2017). IUCrData, 2, x171729. Google Scholar
Ansari, A., Ali, A., Asif, M. & Shamsuzzaman, S. (2017). New J. Chem. 41, 16–41. Web of Science CrossRef CAS Google Scholar
Cambridge Soft (2001). CHEMDRAW Ultra. Cambridge Soft Corporation, Cambridge, Massachusetts, USA. Google Scholar
El-Barbary, A. A., Sakran, M. A., El-Madani, A. M. & Nielsen, C. (2005). J. Heterocycl. Chem. 42, 935–941. CAS Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Oudir, S., Rigo, B., Hénichart, J.-P. & Gautret, P. (2006). Synthesis, pp. 2845–2848. Google Scholar
Panda, N. & Jena, A. K. (2012). J. Org. Chem. 77, 9401–9406. CrossRef CAS Google Scholar
Rigaku OD (2015). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Shie, J.-J. & Fang, J.-M. (2007). J. Org. Chem. 72, 3141–3144. CrossRef CAS Google Scholar
Wu, L.-L., Ge, Y.-C., He, T., Zhang, L., Fu, X.-L., Fu, H.-Y., Chen, H. & Li, R.-X. (2012). Synthesis, 44, 1577–1583. CAS Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.