organic compounds
2-[5-(4-Fluorophenyl)-3-(4-methylphenyl)-4,5-dihydro-1H-pyrazol-1-yl]-4-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)thiazole
aDepartment 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, Giza, Egypt, dDepartment of Chemistry, College of Science, Al-Nahrain University, Baghdad, 64021, Iraq, eNational Center for Petrochemicals Technology, King Abdulaziz City for Science and Technology, PO Box 6086, Riyadh 11442, Saudi Arabia, and fSchool of Chemistry, Cardiff University, Main Building, Park Place, Cardiff CF10 3AT, UK
*Correspondence e-mail: gelhiti@ksu.edu.sa
The title compound, C28H23FN6S, comprises phenyl (A), triazolyl (B), thiazolyl (C), pyrazoyl (D), tolyl (E) and fluorophenyl (F) rings, with twist angles between neighbouring rings pairs A/B, B/C, C/D, D/E and D/F of 64.6 (1), 11.7 (2), 23.5 (2), 8.2 (2) and 73.3 (1)°, respectively. A short intramolecular C—H⋯N contact and a weak intermolecular C—H⋯π interaction occur. The crystal chosen for data collection was found to be an inversion twin.
Keywords: crystal structure; pyrazole; thiazole; 1,2,3-triazole.
CCDC reference: 1897508
Structure description
Triazoles act as antifungal drugs and plant protection fungicides (Bonandi et al., 2017). Thiazoles and pyrazoles are an essential core scaffold in many natural products and have various biological activities (Chhabria et al., 2016; Faria et al., 2017). As part of our studies in these areas, we now describe the synthesis and structure of the title compound.
The molecule of the title compound comprises phenyl (A), triazolyl (B), thiazolyl (C), pyrazoyl (D), tolyl (E) and fluorophenyl (F) rings (Fig. 1). The twist angles between the planes through neighbouring ring pairs A/B, B/C, C/D, D/E and D/F are 64.6 (1), 11.7 (2), 23.5 (2), 8.2 (2) and 73.3 (1)°, respectively. The packing is shown in Fig. 2. A short intramolecular C—H⋯N contact and a weak intermolecular C—H⋯π interaction occur (Table 1); the latter involves the phenyl ring bonded to the triazole ring as donor and the tolyl ring as acceptor.
Synthesis and crystallization
The title compound was synthesized from condensation of 5-(4-fluorophenyl)-3-p-tolyl-4,5-dihydro-1H-pyrazole-1-carbothioamide (0.63 g, 2.0 mmol) with 2-bromo-1-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)ethanone (0.56 g, 2.0 mmol) in anhydrous ethanol (20 ml) under reflux for 2 h. The crude product was recrystallized from dimethylformamide solution to give colourless crystals (74%), m.p. 241–242°C.
Refinement
Crystal data, data collection and structure . The crystal studied was refined as a two-component inversion twin.
details are summarized in Table 2Structural data
CCDC reference: 1897508
https://doi.org/10.1107/S2414314619002402/hb4287sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314619002402/hb4287Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314619002402/hb4287Isup3.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: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows and WinGX (Farrugia, 2012); software used to prepare material for publication: CHEMDRAW Ultra (Cambridge Soft, 2001).C28H23FN6S | Dx = 1.331 Mg m−3 |
Mr = 494.58 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 2536 reflections |
a = 6.4930 (7) Å | θ = 4.5–24.6° |
b = 13.8065 (10) Å | µ = 0.17 mm−1 |
c = 27.539 (2) Å | T = 298 K |
V = 2468.7 (4) Å3 | Block, colourless |
Z = 4 | 0.48 × 0.22 × 0.20 mm |
F(000) = 1032 |
Rigaku Oxford Diffraction SuperNova, Dual, Cu at zero, Atlas diffractometer | 3616 reflections with I > 2σ(I) |
ω scans | Rint = 0.030 |
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2015) | θmax = 29.9°, θmin = 3.5° |
Tmin = 0.989, Tmax = 0.995 | h = −8→6 |
10497 measured reflections | k = −18→18 |
5824 independent reflections | l = −37→37 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.054 | w = 1/[σ2(Fo2) + (0.0443P)2 + 0.4094P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.130 | (Δ/σ)max < 0.001 |
S = 1.02 | Δρmax = 0.19 e Å−3 |
5824 reflections | Δρmin = −0.16 e Å−3 |
328 parameters | Absolute structure: Refined as an inversion twin. |
0 restraints | Absolute structure parameter: 0.39 (13) |
Primary atom site location: structure-invariant direct methods |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refined as a twocomponent inversion twin. All hydrogen atoms were placed in calculated positions (C—H = 0.93–0.97 Å) and refined using a riding model. Their Uiso values were set to 1.2Ueq(C) or 1.5Ueq(methyl C). |
x | y | z | Uiso*/Ueq | ||
C1 | −0.4269 (7) | 1.1919 (3) | 1.07159 (13) | 0.0559 (10) | |
C2 | −0.6229 (7) | 1.1827 (3) | 1.08958 (15) | 0.0649 (11) | |
H2 | −0.678909 | 1.121876 | 1.095562 | 0.078* | |
C3 | −0.7347 (7) | 1.2650 (3) | 1.09859 (16) | 0.0717 (12) | |
H3 | −0.867316 | 1.260334 | 1.111120 | 0.086* | |
C4 | −0.6503 (9) | 1.3551 (3) | 1.08904 (16) | 0.0739 (13) | |
H4 | −0.725943 | 1.410783 | 1.095705 | 0.089* | |
C5 | −0.4596 (9) | 1.3629 (3) | 1.07019 (19) | 0.0849 (15) | |
H5 | −0.404979 | 1.423607 | 1.063286 | 0.102* | |
C6 | −0.3460 (8) | 1.2808 (3) | 1.06117 (18) | 0.0797 (13) | |
H6 | −0.214461 | 1.285781 | 1.048022 | 0.096* | |
C7 | −0.3245 (6) | 1.0401 (2) | 1.02673 (13) | 0.0511 (9) | |
C8 | −0.5093 (7) | 1.0342 (3) | 0.99548 (16) | 0.0691 (12) | |
H8A | −0.513388 | 1.089265 | 0.974237 | 0.104* | |
H8B | −0.630595 | 1.033504 | 1.015412 | 0.104* | |
H8C | −0.503877 | 0.975897 | 0.976504 | 0.104* | |
C9 | −0.1463 (6) | 0.9874 (2) | 1.02874 (13) | 0.0516 (9) | |
C10 | −0.0736 (6) | 0.9082 (3) | 0.99844 (14) | 0.0511 (9) | |
C11 | 0.0948 (7) | 0.8538 (3) | 1.00637 (14) | 0.0574 (10) | |
H11 | 0.182880 | 0.861305 | 1.032728 | 0.069* | |
C12 | −0.0915 (6) | 0.8150 (3) | 0.93398 (14) | 0.0544 (10) | |
C13 | −0.3802 (7) | 0.7884 (2) | 0.87594 (14) | 0.0567 (10) | |
H13 | −0.469753 | 0.783243 | 0.904477 | 0.068* | |
C14 | −0.4096 (7) | 0.6982 (3) | 0.84381 (16) | 0.0690 (12) | |
H14A | −0.524532 | 0.659290 | 0.855039 | 0.083* | |
H14B | −0.432842 | 0.716223 | 0.810208 | 0.083* | |
C15 | −0.2083 (7) | 0.6445 (3) | 0.84956 (15) | 0.0583 (11) | |
C16 | −0.4171 (7) | 0.8849 (3) | 0.85139 (13) | 0.0568 (10) | |
C17 | −0.6006 (8) | 0.9330 (3) | 0.85763 (17) | 0.0816 (14) | |
H17 | −0.701415 | 0.905584 | 0.877291 | 0.098* | |
C18 | −0.6390 (10) | 1.0206 (4) | 0.8355 (2) | 0.0978 (18) | |
H18 | −0.763844 | 1.052494 | 0.839867 | 0.117* | |
C19 | −0.4880 (11) | 1.0591 (3) | 0.80716 (18) | 0.0818 (16) | |
C20 | −0.3074 (10) | 1.0152 (3) | 0.79966 (17) | 0.0804 (15) | |
H20 | −0.208150 | 1.043064 | 0.779691 | 0.097* | |
C21 | −0.2713 (8) | 0.9269 (3) | 0.82245 (16) | 0.0694 (12) | |
H21 | −0.145671 | 0.895904 | 0.817918 | 0.083* | |
C22 | −0.1595 (8) | 0.5513 (3) | 0.82755 (15) | 0.0618 (11) | |
C23 | 0.0365 (8) | 0.5127 (3) | 0.83004 (18) | 0.0740 (13) | |
H23 | 0.140588 | 0.547775 | 0.845171 | 0.089* | |
C24 | 0.0807 (9) | 0.4226 (3) | 0.81034 (19) | 0.0843 (16) | |
H24 | 0.213884 | 0.398120 | 0.812360 | 0.101* | |
C25 | −0.0720 (10) | 0.3686 (3) | 0.78763 (17) | 0.0782 (15) | |
C26 | −0.2671 (9) | 0.4073 (3) | 0.78493 (17) | 0.0820 (15) | |
H26 | −0.371342 | 0.372581 | 0.769661 | 0.098* | |
C27 | −0.3102 (9) | 0.4974 (3) | 0.80466 (16) | 0.0767 (14) | |
H27 | −0.443203 | 0.521997 | 0.802457 | 0.092* | |
C28 | −0.0244 (10) | 0.2676 (4) | 0.7685 (2) | 0.111 (2) | |
H28A | −0.112090 | 0.253675 | 0.741325 | 0.166* | |
H28B | −0.048207 | 0.220881 | 0.793703 | 0.166* | |
H28C | 0.116980 | 0.264634 | 0.758453 | 0.166* | |
N1 | −0.3011 (5) | 1.1082 (2) | 1.06182 (12) | 0.0562 (8) | |
N2 | −0.1185 (6) | 1.0982 (3) | 1.08453 (13) | 0.0734 (10) | |
N3 | −0.0244 (6) | 1.0233 (3) | 1.06502 (14) | 0.0708 (10) | |
N4 | −0.1820 (5) | 0.8870 (2) | 0.95596 (11) | 0.0517 (8) | |
N5 | −0.1641 (5) | 0.7772 (2) | 0.89122 (12) | 0.0595 (8) | |
N6 | −0.0774 (6) | 0.6892 (2) | 0.87665 (12) | 0.0603 (9) | |
F1 | −0.5241 (6) | 1.1462 (2) | 0.78531 (12) | 0.1226 (13) | |
S1 | 0.12603 (17) | 0.76837 (7) | 0.96140 (4) | 0.0631 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.053 (3) | 0.058 (2) | 0.056 (2) | 0.002 (2) | −0.0014 (19) | −0.0004 (19) |
C2 | 0.055 (3) | 0.065 (2) | 0.075 (2) | −0.004 (2) | 0.000 (2) | 0.002 (2) |
C3 | 0.056 (3) | 0.082 (3) | 0.077 (3) | 0.008 (3) | 0.005 (2) | −0.008 (3) |
C4 | 0.086 (4) | 0.062 (3) | 0.074 (3) | 0.012 (3) | −0.005 (3) | −0.008 (2) |
C5 | 0.090 (4) | 0.058 (3) | 0.107 (4) | −0.001 (3) | 0.010 (3) | 0.006 (3) |
C6 | 0.072 (3) | 0.064 (2) | 0.103 (3) | −0.006 (3) | 0.017 (3) | 0.006 (3) |
C7 | 0.045 (2) | 0.0479 (18) | 0.060 (2) | −0.0055 (18) | −0.0047 (19) | 0.0081 (17) |
C8 | 0.056 (3) | 0.075 (3) | 0.077 (3) | 0.006 (2) | −0.013 (2) | −0.012 (2) |
C9 | 0.043 (2) | 0.0507 (18) | 0.061 (2) | −0.0044 (19) | −0.007 (2) | 0.0067 (17) |
C10 | 0.041 (2) | 0.0488 (18) | 0.064 (2) | −0.0031 (18) | −0.0037 (19) | 0.0109 (18) |
C11 | 0.053 (3) | 0.057 (2) | 0.062 (2) | 0.002 (2) | −0.004 (2) | 0.0069 (18) |
C12 | 0.046 (2) | 0.0502 (19) | 0.067 (2) | 0.0020 (19) | 0.002 (2) | 0.0155 (19) |
C13 | 0.049 (2) | 0.057 (2) | 0.064 (2) | 0.009 (2) | −0.004 (2) | 0.0047 (18) |
C14 | 0.065 (3) | 0.054 (2) | 0.088 (3) | 0.002 (2) | −0.007 (3) | −0.002 (2) |
C15 | 0.063 (3) | 0.049 (2) | 0.062 (2) | 0.000 (2) | 0.006 (2) | 0.0085 (19) |
C16 | 0.065 (3) | 0.053 (2) | 0.052 (2) | 0.005 (2) | −0.003 (2) | −0.0015 (18) |
C17 | 0.077 (4) | 0.087 (3) | 0.081 (3) | 0.026 (3) | 0.010 (3) | 0.020 (3) |
C18 | 0.105 (5) | 0.093 (4) | 0.096 (4) | 0.039 (4) | 0.001 (4) | 0.016 (3) |
C19 | 0.124 (5) | 0.057 (3) | 0.065 (3) | 0.014 (3) | −0.019 (3) | 0.003 (2) |
C20 | 0.109 (5) | 0.061 (3) | 0.071 (3) | −0.006 (3) | 0.002 (3) | 0.004 (2) |
C21 | 0.072 (3) | 0.059 (2) | 0.077 (3) | 0.003 (2) | 0.004 (3) | 0.001 (2) |
C22 | 0.070 (3) | 0.050 (2) | 0.065 (2) | 0.005 (2) | 0.006 (2) | 0.0065 (19) |
C23 | 0.074 (4) | 0.061 (3) | 0.088 (3) | −0.003 (2) | 0.016 (3) | −0.006 (2) |
C24 | 0.079 (4) | 0.068 (3) | 0.106 (4) | 0.010 (3) | 0.032 (3) | 0.002 (3) |
C25 | 0.099 (4) | 0.059 (3) | 0.077 (3) | −0.001 (3) | 0.023 (3) | 0.000 (2) |
C26 | 0.097 (4) | 0.068 (3) | 0.081 (3) | 0.000 (3) | −0.009 (3) | −0.005 (3) |
C27 | 0.087 (4) | 0.066 (3) | 0.077 (3) | 0.009 (3) | −0.008 (3) | −0.006 (2) |
C28 | 0.150 (6) | 0.062 (3) | 0.120 (4) | −0.002 (3) | 0.042 (4) | −0.017 (3) |
N1 | 0.048 (2) | 0.0557 (17) | 0.0654 (18) | −0.0025 (16) | −0.0046 (17) | −0.0033 (17) |
N2 | 0.056 (2) | 0.083 (2) | 0.081 (2) | 0.006 (2) | −0.019 (2) | −0.016 (2) |
N3 | 0.056 (2) | 0.074 (2) | 0.082 (2) | 0.0069 (19) | −0.019 (2) | −0.009 (2) |
N4 | 0.0483 (19) | 0.0456 (15) | 0.0613 (18) | 0.0026 (15) | −0.0022 (16) | 0.0077 (15) |
N5 | 0.056 (2) | 0.0556 (17) | 0.0673 (19) | 0.0098 (17) | −0.0044 (17) | −0.0025 (16) |
N6 | 0.062 (2) | 0.0547 (17) | 0.0644 (19) | 0.0076 (18) | 0.0068 (18) | 0.0029 (17) |
F1 | 0.179 (4) | 0.0690 (17) | 0.120 (2) | 0.023 (2) | −0.030 (2) | 0.0235 (17) |
S1 | 0.0522 (6) | 0.0618 (5) | 0.0754 (6) | 0.0127 (5) | −0.0014 (6) | 0.0094 (5) |
C1—C6 | 1.366 (5) | C14—H14A | 0.9700 |
C1—C2 | 1.372 (6) | C14—H14B | 0.9700 |
C1—N1 | 1.440 (5) | C15—N6 | 1.288 (5) |
C2—C3 | 1.371 (6) | C15—C22 | 1.458 (5) |
C2—H2 | 0.9300 | C16—C21 | 1.367 (6) |
C3—C4 | 1.385 (6) | C16—C17 | 1.374 (6) |
C3—H3 | 0.9300 | C17—C18 | 1.378 (6) |
C4—C5 | 1.347 (7) | C17—H17 | 0.9300 |
C4—H4 | 0.9300 | C18—C19 | 1.361 (8) |
C5—C6 | 1.375 (6) | C18—H18 | 0.9300 |
C5—H5 | 0.9300 | C19—C20 | 1.336 (8) |
C6—H6 | 0.9300 | C19—F1 | 1.366 (5) |
C7—N1 | 1.357 (4) | C20—C21 | 1.391 (6) |
C7—C9 | 1.368 (5) | C20—H20 | 0.9300 |
C7—C8 | 1.479 (6) | C21—H21 | 0.9300 |
C8—H8A | 0.9600 | C22—C23 | 1.381 (6) |
C8—H8B | 0.9600 | C22—C27 | 1.381 (6) |
C8—H8C | 0.9600 | C23—C24 | 1.387 (6) |
C9—N3 | 1.368 (5) | C23—H23 | 0.9300 |
C9—C10 | 1.454 (5) | C24—C25 | 1.389 (7) |
C10—C11 | 1.344 (5) | C24—H24 | 0.9300 |
C10—N4 | 1.396 (5) | C25—C26 | 1.377 (7) |
C11—S1 | 1.722 (4) | C25—C28 | 1.522 (6) |
C11—H11 | 0.9300 | C26—C27 | 1.385 (6) |
C12—N4 | 1.304 (5) | C26—H26 | 0.9300 |
C12—N5 | 1.371 (5) | C27—H27 | 0.9300 |
C12—S1 | 1.726 (4) | C28—H28A | 0.9600 |
C13—N5 | 1.473 (5) | C28—H28B | 0.9600 |
C13—C16 | 1.513 (5) | C28—H28C | 0.9600 |
C13—C14 | 1.540 (5) | N1—N2 | 1.348 (5) |
C13—H13 | 0.9800 | N2—N3 | 1.315 (5) |
C14—C15 | 1.511 (6) | N5—N6 | 1.398 (4) |
C6—C1—C2 | 121.1 (4) | C21—C16—C17 | 117.9 (4) |
C6—C1—N1 | 117.6 (4) | C21—C16—C13 | 121.7 (4) |
C2—C1—N1 | 121.3 (4) | C17—C16—C13 | 120.4 (4) |
C3—C2—C1 | 118.7 (4) | C16—C17—C18 | 121.7 (5) |
C3—C2—H2 | 120.7 | C16—C17—H17 | 119.1 |
C1—C2—H2 | 120.7 | C18—C17—H17 | 119.1 |
C2—C3—C4 | 120.1 (4) | C19—C18—C17 | 117.8 (5) |
C2—C3—H3 | 120.0 | C19—C18—H18 | 121.1 |
C4—C3—H3 | 120.0 | C17—C18—H18 | 121.1 |
C5—C4—C3 | 120.5 (4) | C20—C19—C18 | 123.0 (5) |
C5—C4—H4 | 119.7 | C20—C19—F1 | 118.8 (6) |
C3—C4—H4 | 119.7 | C18—C19—F1 | 118.2 (6) |
C4—C5—C6 | 119.8 (5) | C19—C20—C21 | 118.3 (5) |
C4—C5—H5 | 120.1 | C19—C20—H20 | 120.8 |
C6—C5—H5 | 120.1 | C21—C20—H20 | 120.8 |
C1—C6—C5 | 119.8 (5) | C16—C21—C20 | 121.3 (5) |
C1—C6—H6 | 120.1 | C16—C21—H21 | 119.4 |
C5—C6—H6 | 120.1 | C20—C21—H21 | 119.4 |
N1—C7—C9 | 104.2 (3) | C23—C22—C27 | 117.9 (4) |
N1—C7—C8 | 122.9 (4) | C23—C22—C15 | 121.3 (4) |
C9—C7—C8 | 132.9 (4) | C27—C22—C15 | 120.8 (4) |
C7—C8—H8A | 109.5 | C22—C23—C24 | 121.1 (5) |
C7—C8—H8B | 109.5 | C22—C23—H23 | 119.4 |
H8A—C8—H8B | 109.5 | C24—C23—H23 | 119.4 |
C7—C8—H8C | 109.5 | C23—C24—C25 | 120.6 (5) |
H8A—C8—H8C | 109.5 | C23—C24—H24 | 119.7 |
H8B—C8—H8C | 109.5 | C25—C24—H24 | 119.7 |
N3—C9—C7 | 109.1 (3) | C26—C25—C24 | 118.2 (4) |
N3—C9—C10 | 120.2 (4) | C26—C25—C28 | 121.6 (5) |
C7—C9—C10 | 130.6 (4) | C24—C25—C28 | 120.2 (6) |
C11—C10—N4 | 115.4 (3) | C25—C26—C27 | 120.9 (5) |
C11—C10—C9 | 126.2 (4) | C25—C26—H26 | 119.6 |
N4—C10—C9 | 118.4 (3) | C27—C26—H26 | 119.6 |
C10—C11—S1 | 111.2 (3) | C22—C27—C26 | 121.3 (5) |
C10—C11—H11 | 124.4 | C22—C27—H27 | 119.4 |
S1—C11—H11 | 124.4 | C26—C27—H27 | 119.4 |
N4—C12—N5 | 122.3 (4) | C25—C28—H28A | 109.5 |
N4—C12—S1 | 116.7 (3) | C25—C28—H28B | 109.5 |
N5—C12—S1 | 121.0 (3) | H28A—C28—H28B | 109.5 |
N5—C13—C16 | 111.8 (3) | C25—C28—H28C | 109.5 |
N5—C13—C14 | 101.4 (3) | H28A—C28—H28C | 109.5 |
C16—C13—C14 | 115.8 (3) | H28B—C28—H28C | 109.5 |
N5—C13—H13 | 109.2 | N2—N1—C7 | 110.9 (3) |
C16—C13—H13 | 109.2 | N2—N1—C1 | 119.7 (3) |
C14—C13—H13 | 109.2 | C7—N1—C1 | 128.7 (3) |
C15—C14—C13 | 103.3 (4) | N3—N2—N1 | 107.5 (3) |
C15—C14—H14A | 111.1 | N2—N3—C9 | 108.3 (3) |
C13—C14—H14A | 111.1 | C12—N4—C10 | 108.8 (3) |
C15—C14—H14B | 111.1 | C12—N5—N6 | 116.0 (3) |
C13—C14—H14B | 111.1 | C12—N5—C13 | 122.2 (3) |
H14A—C14—H14B | 109.1 | N6—N5—C13 | 113.1 (3) |
N6—C15—C22 | 121.4 (4) | C15—N6—N5 | 108.5 (3) |
N6—C15—C14 | 113.4 (3) | C11—S1—C12 | 87.9 (2) |
C22—C15—C14 | 125.3 (4) |
Cg6 is the centroid of the C22–C27 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8C···N4 | 0.96 | 2.49 | 3.135 (5) | 125 |
C2—H2···Cg6i | 0.93 | 2.93 | 3.451 (5) | 117 |
Symmetry code: (i) x−1/2, −y+3/2, −z+2. |
Footnotes
‡Additional correspondence author, e-mail: kariukib@cardiff.ac.uk.
Funding information
MHA thanks King Abdulaziz City for Science and Technology (KACST), Saudi Arabia for financial support (award No. 020–0180).
References
Bonandi, E., Christodoulou, M. S., Fumagalli, G., Perdicchia, D., Rastelli, G. & Passarella, D. (2017). Drug Discov. Today, 22, 1572–1581. Web of Science CrossRef CAS Google Scholar
Cambridge Soft (2001). CHEMDRAW Ultra. Cambridge Soft Corporation, Cambridge, Massachusetts, USA. Google Scholar
Chhabria, M. T., Patel, S., Modi, P. & Brahmkshatriya, P. S. (2016). Curr. Top. Med. Chem. 16, 2841–2862. CAS Google Scholar
Faria, J. V., Vegi, P. F., Miguita, A. G. C., Dos Santos, M. S., Boechat, N. & Bernardino, A. M. R. (2017). Bioorg. Med. Chem. 25, 5891–5903. CrossRef CAS Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, 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
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