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)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, Giza, Egypt, dNational Center for Petrochemicals Technology, King Abdulaziz City for Science and Technology, PO Box 6086, Riyadh 11442, Saudi Arabia, and eSchool of Chemistry, Cardiff University, Main Building, Park Place, Cardiff CF10 3AT, Wales
*Correspondence e-mail: gelhiti@ksu.edu.sa
In the title compound, C37H28BrClN8O, the linked chlorophenyl, pyrazolyl and thiazolyl ringss are almost coplanar, with dihedral angles of 0.6 (3)° between the chlorophenyl and pyrazolyl rings and 5.4 (3)° between the pyrazolyl and thiazolyl rings. The dihedral angle between the thiazolyl and bromophenyl rings is 17.5 (2)°. The central pyrazolyl rings subtend a dihedral angle of 67.7 (1)°. In the crystal, π–π and C—H⋯Br interactions link the molecules to form columns parallel to [010]. The π–π interactions involve partially overlapping nonparallel bromophenyl and tolyl groups.
Keywords: crystal structure; π–π stacking; heterocycles.
CCDC reference: 1815108
Structure description
Various procedures have been reported for the synthesis of heterocycles containing the pyrazolinylthiazole moiety (Abdel-Wahab et al., 2009; Abid & Azam, 2006; Bonacorso et al., 2002). Both pyrazolyltriazoles and 1-thiazol-2-ylpyrazolines show various antimicrobial (Abdel-Wahab et al., 2012, 2017), antitumor and antimycobacterial activities (Kumar et al., 2003).
The 37H28BrClN8O (Fig. 1). Contact between neighbouring molecules includes π–π and C—H⋯Br interactions (Table 1, Fig. 2) to form columns parallel to [010]. The π–π interactions involve partially overlapping bromophenyl and tolyl groups with a centroid-to-centroid distance of 3.993 (2) Å. The planes of the two groups are not parallel, however, with an interplanar angle of ca 15°.
comprises a single molecule of CSynthesis and crystallization
4-(4-Bromophenyl)-2-(3-(4-chlorophenyl)-5-{3-[5-methyl-1-(4-tolyl)-1H-1,2,3-triazol-4-yl]-1-phenyl-1H-pyrazol-4-yl}-4,5-dihydro-1H-pyrazol-1-yl)thiazole was synthesized in 83% yield from reaction of 3-(4-chlorophenyl)-5-{3-[5-methyl-1-(4-tolyl)-1H-1,2,3-triazol-4-yl]-1-phenyl-1H-pyrazol-4-yl}-4,5-dihydro-1H-pyrazole-1-carbothioamide and 2-bromo-1-(4-bromophenyl)ethanone in ethanol under reflux for 2 h. Colourless crystals (m.p. 279–281°C, lit. 279–281°C; Abdel-Wahab et al., 2017) were obtained by recrystallization of the crude product obtained following work-up using dimethylformamide as the solvent.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1815108
https://doi.org/10.1107/S2414314618000366/xu4033sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314618000366/xu4033Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314618000366/xu4033Isup3.cml
Data collection: CrysAlis PRO (Agilent, 2014); cell
CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); 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 = 1.455 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 10.4220 (7) Å | Cell parameters from 2941 reflections |
b = 13.4232 (5) Å | θ = 3.5–23.9° |
c = 23.8943 (14) Å | µ = 1.41 mm−1 |
β = 90.198 (6)° | T = 296 K |
V = 3342.7 (3) Å3 | Needle, colourless |
Z = 4 | 0.42 × 0.10 × 0.04 mm |
Agilent SuperNova, Dual, Cu at zero, Atlas diffractometer | 3958 reflections with I > 2σ(I) |
ω scans | Rint = 0.039 |
Absorption correction: gaussian (CrysAlis PRO; Agilent, 2014) | θmax = 29.9°, θmin = 3.0° |
Tmin = 0.794, Tmax = 1.000 | h = −13→13 |
15250 measured reflections | k = −18→13 |
7792 independent reflections | l = −32→24 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.063 | H-atom parameters constrained |
wR(F2) = 0.183 | w = 1/[σ2(Fo2) + (0.0663P)2 + 2.0474P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
7792 reflections | Δρmax = 0.77 e Å−3 |
435 parameters | Δρmin = −0.95 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. |
Refinement. Non-hydrogen atoms were refined with anisotropic displacement parameters. All hydrogen atoms were placed in calculated positions and refined using a riding model. Methine C—H bonds were fixed at 0.98 Å, with displacement parameters 1.2 times Ueq(C). Ethyl C—H bonds were fixed at 0.97 Å, with displacement parameters 1.2 times Ueq(C). Methyl C—H bonds were fixed at 0.96 Å, with displacement parameters 1.5 times Ueq(C), and were allowed to spin about the C—C bond. Aromatic C—H distances were set to 0.93 Å and their Uiso(H) set to 1.2 times the Ueq(C). |
x | y | z | Uiso*/Ueq | ||
C1 | −0.0099 (4) | 0.4942 (3) | 0.33097 (16) | 0.0498 (9) | |
C2 | −0.0953 (4) | 0.5332 (3) | 0.29246 (18) | 0.0607 (11) | |
H2 | −0.0901 | 0.6003 | 0.2831 | 0.073* | |
C3 | −0.1882 (4) | 0.4747 (3) | 0.26767 (19) | 0.0688 (12) | |
H3 | −0.2451 | 0.5022 | 0.2419 | 0.083* | |
C4 | −0.1960 (4) | 0.3762 (3) | 0.28134 (19) | 0.0623 (11) | |
C5 | −0.1140 (4) | 0.3358 (3) | 0.3204 (2) | 0.0648 (12) | |
H5 | −0.1209 | 0.2689 | 0.3300 | 0.078* | |
C6 | −0.0220 (4) | 0.3943 (3) | 0.34518 (18) | 0.0581 (11) | |
H6 | 0.0328 | 0.3668 | 0.3718 | 0.070* | |
C7 | 0.0919 (4) | 0.5579 (3) | 0.35531 (16) | 0.0491 (9) | |
C8 | 0.1620 (4) | 0.5379 (3) | 0.40160 (18) | 0.0597 (11) | |
H8 | 0.1527 | 0.4810 | 0.4234 | 0.072* | |
C9 | 0.2136 (4) | 0.6910 (3) | 0.35524 (15) | 0.0482 (9) | |
C10 | 0.3825 (4) | 0.9098 (3) | 0.34920 (16) | 0.0474 (9) | |
C11 | 0.3075 (4) | 0.9318 (3) | 0.29734 (16) | 0.0568 (11) | |
H11A | 0.3638 | 0.9422 | 0.2657 | 0.068* | |
H11B | 0.2542 | 0.9903 | 0.3022 | 0.068* | |
C12 | 0.2252 (4) | 0.8382 (3) | 0.28926 (15) | 0.0487 (9) | |
H12 | 0.1340 | 0.8544 | 0.2931 | 0.058* | |
C13 | 0.4759 (4) | 0.9774 (3) | 0.37459 (16) | 0.0501 (9) | |
C14 | 0.5408 (4) | 0.9515 (3) | 0.4233 (2) | 0.0715 (13) | |
H14 | 0.5252 | 0.8899 | 0.4399 | 0.086* | |
C15 | 0.6282 (5) | 1.0159 (3) | 0.4476 (2) | 0.0831 (15) | |
H15 | 0.6713 | 0.9978 | 0.4802 | 0.100* | |
C16 | 0.6511 (4) | 1.1068 (3) | 0.4232 (2) | 0.0659 (12) | |
C17 | 0.5883 (5) | 1.1349 (3) | 0.37556 (19) | 0.0679 (12) | |
H17 | 0.6047 | 1.1966 | 0.3593 | 0.082* | |
C18 | 0.4996 (4) | 1.0703 (3) | 0.35153 (18) | 0.0611 (11) | |
H18 | 0.4555 | 1.0898 | 0.3195 | 0.073* | |
C19 | 0.2493 (4) | 0.7877 (2) | 0.23490 (15) | 0.0440 (8) | |
C20 | 0.3277 (4) | 0.7084 (2) | 0.22460 (15) | 0.0471 (9) | |
H20 | 0.3740 | 0.6728 | 0.2513 | 0.057* | |
C21 | 0.2008 (4) | 0.8139 (2) | 0.18121 (15) | 0.0449 (9) | |
C22 | 0.3920 (4) | 0.6132 (2) | 0.13991 (15) | 0.0469 (9) | |
C23 | 0.3448 (4) | 0.5813 (3) | 0.08881 (17) | 0.0611 (11) | |
H23 | 0.2739 | 0.6121 | 0.0726 | 0.073* | |
C24 | 0.4049 (5) | 0.5027 (4) | 0.0624 (2) | 0.0838 (15) | |
H24 | 0.3743 | 0.4800 | 0.0281 | 0.101* | |
C25 | 0.5106 (5) | 0.4577 (4) | 0.0869 (2) | 0.0829 (15) | |
H25 | 0.5501 | 0.4043 | 0.0691 | 0.099* | |
C26 | 0.5570 (5) | 0.4910 (3) | 0.1368 (2) | 0.0729 (13) | |
H26 | 0.6286 | 0.4609 | 0.1528 | 0.087* | |
C27 | 0.4981 (4) | 0.5691 (3) | 0.16364 (17) | 0.0568 (10) | |
H27 | 0.5299 | 0.5919 | 0.1977 | 0.068* | |
C28 | 0.1107 (4) | 0.8942 (3) | 0.16787 (15) | 0.0456 (9) | |
C29 | 0.0411 (4) | 0.9133 (3) | 0.12035 (15) | 0.0457 (9) | |
C30 | 0.0442 (4) | 0.8669 (3) | 0.06355 (16) | 0.0575 (10) | |
H30A | −0.0321 | 0.8280 | 0.0579 | 0.086* | |
H30B | 0.1182 | 0.8247 | 0.0606 | 0.086* | |
H30C | 0.0483 | 0.9183 | 0.0357 | 0.086* | |
C31 | −0.1280 (4) | 1.0448 (3) | 0.10234 (15) | 0.0468 (9) | |
C32 | −0.1308 (4) | 1.1480 (3) | 0.10141 (19) | 0.0610 (11) | |
H32 | −0.0677 | 1.1848 | 0.1197 | 0.073* | |
C33 | −0.2283 (4) | 1.1950 (3) | 0.0731 (2) | 0.0637 (12) | |
H33 | −0.2305 | 1.2642 | 0.0729 | 0.076* | |
C34 | −0.3234 (4) | 1.1431 (3) | 0.04488 (16) | 0.0522 (9) | |
C35 | −0.3173 (4) | 1.0401 (3) | 0.04686 (16) | 0.0509 (9) | |
H35 | −0.3799 | 1.0029 | 0.0285 | 0.061* | |
C36 | −0.2212 (4) | 0.9914 (3) | 0.07533 (16) | 0.0496 (9) | |
H36 | −0.2195 | 0.9222 | 0.0762 | 0.060* | |
C37 | −0.4290 (4) | 1.1953 (3) | 0.0139 (2) | 0.0728 (13) | |
H37A | −0.4940 | 1.2158 | 0.0398 | 0.109* | |
H37B | −0.4657 | 1.1509 | −0.0133 | 0.109* | |
H37C | −0.3949 | 1.2528 | −0.0048 | 0.109* | |
N1 | 0.1209 (3) | 0.6470 (2) | 0.32887 (13) | 0.0504 (8) | |
N2 | 0.2693 (3) | 0.7769 (2) | 0.33713 (13) | 0.0543 (8) | |
N3 | 0.3588 (3) | 0.8233 (2) | 0.37024 (13) | 0.0518 (8) | |
N4 | 0.3263 (3) | 0.6905 (2) | 0.16892 (12) | 0.0453 (7) | |
N5 | 0.2478 (3) | 0.7548 (2) | 0.14118 (12) | 0.0476 (7) | |
N7 | 0.0817 (3) | 0.9641 (2) | 0.20710 (13) | 0.0566 (8) | |
N8 | −0.0038 (3) | 1.0250 (2) | 0.18692 (14) | 0.0565 (8) | |
N9 | −0.0303 (3) | 0.9945 (2) | 0.13380 (13) | 0.0475 (7) | |
Cl1 | 0.76129 (15) | 1.18779 (9) | 0.45379 (7) | 0.1031 (5) | |
S1 | 0.27060 (11) | 0.63119 (8) | 0.41492 (5) | 0.0611 (3) | |
Br1 | −0.31987 (7) | 0.29441 (4) | 0.24515 (3) | 0.1046 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.053 (2) | 0.0446 (19) | 0.052 (2) | 0.0050 (17) | 0.0076 (19) | 0.0015 (17) |
C2 | 0.068 (3) | 0.044 (2) | 0.070 (3) | −0.0030 (19) | −0.008 (2) | 0.011 (2) |
C3 | 0.077 (3) | 0.053 (2) | 0.075 (3) | −0.008 (2) | −0.022 (3) | 0.011 (2) |
C4 | 0.069 (3) | 0.046 (2) | 0.072 (3) | −0.0075 (19) | 0.000 (2) | 0.000 (2) |
C5 | 0.070 (3) | 0.0405 (19) | 0.084 (3) | 0.000 (2) | 0.003 (3) | 0.003 (2) |
C6 | 0.056 (3) | 0.050 (2) | 0.069 (3) | 0.0066 (19) | 0.005 (2) | 0.010 (2) |
C7 | 0.049 (2) | 0.0468 (19) | 0.051 (2) | 0.0057 (17) | 0.0093 (19) | 0.0021 (17) |
C8 | 0.061 (3) | 0.061 (2) | 0.058 (3) | −0.004 (2) | −0.001 (2) | 0.016 (2) |
C9 | 0.053 (3) | 0.051 (2) | 0.041 (2) | 0.0031 (18) | 0.0031 (19) | −0.0026 (17) |
C10 | 0.048 (2) | 0.0457 (19) | 0.048 (2) | 0.0051 (17) | 0.0010 (18) | −0.0052 (17) |
C11 | 0.082 (3) | 0.0433 (19) | 0.045 (2) | 0.0012 (19) | −0.008 (2) | −0.0041 (17) |
C12 | 0.058 (2) | 0.0469 (19) | 0.041 (2) | 0.0005 (17) | −0.0014 (18) | −0.0009 (16) |
C13 | 0.053 (2) | 0.048 (2) | 0.049 (2) | 0.0027 (17) | 0.0001 (19) | −0.0025 (17) |
C14 | 0.072 (3) | 0.060 (2) | 0.083 (3) | −0.008 (2) | −0.023 (3) | 0.014 (2) |
C15 | 0.078 (4) | 0.075 (3) | 0.096 (4) | −0.007 (3) | −0.038 (3) | 0.011 (3) |
C16 | 0.058 (3) | 0.059 (2) | 0.081 (3) | −0.005 (2) | −0.013 (2) | −0.005 (2) |
C17 | 0.083 (3) | 0.049 (2) | 0.071 (3) | −0.006 (2) | −0.002 (3) | −0.002 (2) |
C18 | 0.076 (3) | 0.051 (2) | 0.056 (2) | −0.001 (2) | −0.008 (2) | −0.0019 (19) |
C19 | 0.050 (2) | 0.0399 (17) | 0.042 (2) | −0.0033 (16) | −0.0040 (17) | −0.0016 (15) |
C20 | 0.059 (3) | 0.0429 (19) | 0.039 (2) | −0.0002 (17) | −0.0070 (18) | −0.0001 (15) |
C21 | 0.046 (2) | 0.0449 (18) | 0.044 (2) | −0.0017 (16) | −0.0061 (17) | −0.0042 (16) |
C22 | 0.052 (2) | 0.0425 (18) | 0.046 (2) | 0.0005 (17) | 0.0034 (18) | −0.0008 (16) |
C23 | 0.061 (3) | 0.070 (3) | 0.052 (2) | 0.004 (2) | −0.006 (2) | −0.014 (2) |
C24 | 0.092 (4) | 0.097 (3) | 0.063 (3) | 0.013 (3) | −0.014 (3) | −0.035 (3) |
C25 | 0.096 (4) | 0.074 (3) | 0.079 (4) | 0.026 (3) | 0.003 (3) | −0.021 (3) |
C26 | 0.088 (4) | 0.067 (3) | 0.063 (3) | 0.025 (2) | −0.002 (3) | −0.006 (2) |
C27 | 0.066 (3) | 0.054 (2) | 0.050 (2) | 0.008 (2) | −0.006 (2) | −0.0020 (19) |
C28 | 0.046 (2) | 0.0460 (18) | 0.044 (2) | 0.0007 (16) | −0.0041 (17) | −0.0040 (16) |
C29 | 0.047 (2) | 0.0441 (18) | 0.046 (2) | 0.0012 (16) | −0.0046 (18) | −0.0011 (16) |
C30 | 0.067 (3) | 0.062 (2) | 0.044 (2) | 0.009 (2) | −0.004 (2) | −0.0053 (19) |
C31 | 0.048 (2) | 0.0485 (19) | 0.044 (2) | 0.0026 (17) | −0.0044 (18) | −0.0001 (17) |
C32 | 0.055 (3) | 0.049 (2) | 0.079 (3) | 0.0033 (19) | −0.019 (2) | −0.009 (2) |
C33 | 0.064 (3) | 0.041 (2) | 0.085 (3) | 0.0061 (19) | −0.009 (2) | −0.002 (2) |
C34 | 0.051 (2) | 0.052 (2) | 0.054 (2) | 0.0030 (18) | −0.0045 (19) | 0.0001 (18) |
C35 | 0.051 (2) | 0.051 (2) | 0.051 (2) | −0.0030 (18) | −0.0098 (19) | 0.0009 (18) |
C36 | 0.053 (2) | 0.0419 (18) | 0.054 (2) | −0.0043 (17) | −0.0038 (19) | 0.0031 (17) |
C37 | 0.068 (3) | 0.061 (3) | 0.089 (3) | 0.012 (2) | −0.022 (3) | 0.003 (2) |
N1 | 0.061 (2) | 0.0459 (16) | 0.0442 (18) | −0.0017 (15) | −0.0005 (16) | 0.0034 (14) |
N2 | 0.068 (2) | 0.0512 (17) | 0.0442 (18) | −0.0110 (16) | −0.0103 (17) | 0.0055 (15) |
N3 | 0.057 (2) | 0.0542 (18) | 0.0445 (18) | −0.0003 (15) | −0.0053 (16) | −0.0008 (15) |
N4 | 0.053 (2) | 0.0412 (15) | 0.0418 (17) | 0.0041 (13) | −0.0021 (15) | −0.0017 (13) |
N5 | 0.054 (2) | 0.0466 (16) | 0.0424 (17) | 0.0032 (14) | −0.0062 (15) | −0.0001 (14) |
N7 | 0.061 (2) | 0.0561 (18) | 0.053 (2) | 0.0097 (16) | −0.0135 (17) | −0.0093 (16) |
N8 | 0.060 (2) | 0.0588 (19) | 0.051 (2) | 0.0098 (16) | −0.0119 (16) | −0.0110 (16) |
N9 | 0.0463 (19) | 0.0486 (16) | 0.0476 (18) | 0.0028 (14) | −0.0072 (15) | −0.0050 (14) |
Cl1 | 0.1052 (12) | 0.0701 (7) | 0.1337 (13) | −0.0203 (7) | −0.0471 (10) | −0.0058 (8) |
S1 | 0.0605 (7) | 0.0698 (6) | 0.0529 (6) | −0.0044 (5) | −0.0073 (5) | 0.0115 (5) |
Br1 | 0.1295 (6) | 0.0716 (3) | 0.1125 (5) | −0.0373 (3) | −0.0330 (4) | 0.0029 (3) |
C1—C2 | 1.381 (5) | C20—H20 | 0.9300 |
C1—C6 | 1.389 (5) | C21—N5 | 1.336 (4) |
C1—C7 | 1.481 (5) | C21—C28 | 1.464 (5) |
C2—C3 | 1.378 (6) | C22—C27 | 1.375 (5) |
C2—H2 | 0.9300 | C22—C23 | 1.383 (5) |
C3—C4 | 1.365 (6) | C22—N4 | 1.424 (4) |
C3—H3 | 0.9300 | C23—C24 | 1.380 (6) |
C4—C5 | 1.375 (6) | C23—H23 | 0.9300 |
C4—Br1 | 1.900 (4) | C24—C25 | 1.384 (6) |
C5—C6 | 1.372 (6) | C24—H24 | 0.9300 |
C5—H5 | 0.9300 | C25—C26 | 1.361 (6) |
C6—H6 | 0.9300 | C25—H25 | 0.9300 |
C7—C8 | 1.351 (5) | C26—C27 | 1.374 (6) |
C7—N1 | 1.386 (5) | C26—H26 | 0.9300 |
C8—S1 | 1.717 (4) | C27—H27 | 0.9300 |
C8—H8 | 0.9300 | C28—N7 | 1.361 (4) |
C9—N1 | 1.295 (5) | C28—C29 | 1.370 (5) |
C9—N2 | 1.362 (5) | C29—N9 | 1.360 (4) |
C9—S1 | 1.739 (4) | C29—C30 | 1.493 (5) |
C10—N3 | 1.289 (5) | C30—H30A | 0.9600 |
C10—C13 | 1.461 (5) | C30—H30B | 0.9600 |
C10—C11 | 1.493 (5) | C30—H30C | 0.9600 |
C11—C12 | 1.532 (5) | C31—C36 | 1.367 (5) |
C11—H11A | 0.9700 | C31—C32 | 1.385 (5) |
C11—H11B | 0.9700 | C31—N9 | 1.433 (5) |
C12—N2 | 1.481 (5) | C32—C33 | 1.372 (6) |
C12—C19 | 1.487 (5) | C32—H32 | 0.9300 |
C12—H12 | 0.9800 | C33—C34 | 1.385 (6) |
C13—C18 | 1.387 (5) | C33—H33 | 0.9300 |
C13—C14 | 1.389 (6) | C34—C35 | 1.386 (5) |
C14—C15 | 1.382 (6) | C34—C37 | 1.499 (5) |
C14—H14 | 0.9300 | C35—C36 | 1.374 (5) |
C15—C16 | 1.373 (6) | C35—H35 | 0.9300 |
C15—H15 | 0.9300 | C36—H36 | 0.9300 |
C16—C17 | 1.365 (6) | C37—H37A | 0.9600 |
C16—Cl1 | 1.740 (4) | C37—H37B | 0.9600 |
C17—C18 | 1.390 (6) | C37—H37C | 0.9600 |
C17—H17 | 0.9300 | N2—N3 | 1.371 (4) |
C18—H18 | 0.9300 | N4—N5 | 1.361 (4) |
C19—C20 | 1.365 (5) | N7—N8 | 1.302 (4) |
C19—C21 | 1.421 (5) | N8—N9 | 1.361 (4) |
C20—N4 | 1.352 (4) | ||
C2—C1—C6 | 118.0 (4) | C27—C22—C23 | 120.9 (4) |
C2—C1—C7 | 120.1 (3) | C27—C22—N4 | 120.0 (3) |
C6—C1—C7 | 121.9 (4) | C23—C22—N4 | 119.0 (4) |
C3—C2—C1 | 121.4 (4) | C24—C23—C22 | 118.7 (4) |
C3—C2—H2 | 119.3 | C24—C23—H23 | 120.7 |
C1—C2—H2 | 119.3 | C22—C23—H23 | 120.7 |
C4—C3—C2 | 119.4 (4) | C23—C24—C25 | 120.1 (4) |
C4—C3—H3 | 120.3 | C23—C24—H24 | 119.9 |
C2—C3—H3 | 120.3 | C25—C24—H24 | 119.9 |
C3—C4—C5 | 120.4 (4) | C26—C25—C24 | 120.4 (4) |
C3—C4—Br1 | 119.5 (4) | C26—C25—H25 | 119.8 |
C5—C4—Br1 | 120.1 (3) | C24—C25—H25 | 119.8 |
C6—C5—C4 | 120.0 (4) | C25—C26—C27 | 120.1 (4) |
C6—C5—H5 | 120.0 | C25—C26—H26 | 119.9 |
C4—C5—H5 | 120.0 | C27—C26—H26 | 119.9 |
C5—C6—C1 | 120.7 (4) | C26—C27—C22 | 119.7 (4) |
C5—C6—H6 | 119.6 | C26—C27—H27 | 120.1 |
C1—C6—H6 | 119.6 | C22—C27—H27 | 120.1 |
C8—C7—N1 | 115.3 (4) | N7—C28—C29 | 108.9 (3) |
C8—C7—C1 | 126.2 (3) | N7—C28—C21 | 120.1 (3) |
N1—C7—C1 | 118.5 (3) | C29—C28—C21 | 131.0 (3) |
C7—C8—S1 | 111.1 (3) | N9—C29—C28 | 104.0 (3) |
C7—C8—H8 | 124.4 | N9—C29—C30 | 124.2 (3) |
S1—C8—H8 | 124.4 | C28—C29—C30 | 131.5 (3) |
N1—C9—N2 | 123.3 (3) | C29—C30—H30A | 109.5 |
N1—C9—S1 | 116.1 (3) | C29—C30—H30B | 109.5 |
N2—C9—S1 | 120.5 (3) | H30A—C30—H30B | 109.5 |
N3—C10—C13 | 121.7 (3) | C29—C30—H30C | 109.5 |
N3—C10—C11 | 113.7 (3) | H30A—C30—H30C | 109.5 |
C13—C10—C11 | 124.6 (3) | H30B—C30—H30C | 109.5 |
C10—C11—C12 | 103.5 (3) | C36—C31—C32 | 120.1 (4) |
C10—C11—H11A | 111.1 | C36—C31—N9 | 120.2 (3) |
C12—C11—H11A | 111.1 | C32—C31—N9 | 119.6 (3) |
C10—C11—H11B | 111.1 | C33—C32—C31 | 118.9 (4) |
C12—C11—H11B | 111.1 | C33—C32—H32 | 120.5 |
H11A—C11—H11B | 109.0 | C31—C32—H32 | 120.5 |
N2—C12—C19 | 111.6 (3) | C32—C33—C34 | 122.5 (4) |
N2—C12—C11 | 100.7 (3) | C32—C33—H33 | 118.8 |
C19—C12—C11 | 112.8 (3) | C34—C33—H33 | 118.8 |
N2—C12—H12 | 110.4 | C33—C34—C35 | 116.9 (4) |
C19—C12—H12 | 110.4 | C33—C34—C37 | 122.0 (4) |
C11—C12—H12 | 110.4 | C35—C34—C37 | 121.1 (4) |
C18—C13—C14 | 118.1 (4) | C36—C35—C34 | 121.6 (4) |
C18—C13—C10 | 120.9 (4) | C36—C35—H35 | 119.2 |
C14—C13—C10 | 120.9 (4) | C34—C35—H35 | 119.2 |
C15—C14—C13 | 120.9 (4) | C31—C36—C35 | 120.0 (3) |
C15—C14—H14 | 119.6 | C31—C36—H36 | 120.0 |
C13—C14—H14 | 119.6 | C35—C36—H36 | 120.0 |
C16—C15—C14 | 119.6 (4) | C34—C37—H37A | 109.5 |
C16—C15—H15 | 120.2 | C34—C37—H37B | 109.5 |
C14—C15—H15 | 120.2 | H37A—C37—H37B | 109.5 |
C17—C16—C15 | 121.1 (4) | C34—C37—H37C | 109.5 |
C17—C16—Cl1 | 119.4 (3) | H37A—C37—H37C | 109.5 |
C15—C16—Cl1 | 119.5 (4) | H37B—C37—H37C | 109.5 |
C16—C17—C18 | 119.2 (4) | C9—N1—C7 | 109.6 (3) |
C16—C17—H17 | 120.4 | C9—N2—N3 | 119.4 (3) |
C18—C17—H17 | 120.4 | C9—N2—C12 | 125.8 (3) |
C13—C18—C17 | 121.1 (4) | N3—N2—C12 | 113.7 (3) |
C13—C18—H18 | 119.5 | C10—N3—N2 | 108.3 (3) |
C17—C18—H18 | 119.5 | C20—N4—N5 | 111.8 (3) |
C20—C19—C21 | 104.0 (3) | C20—N4—C22 | 127.2 (3) |
C20—C19—C12 | 128.0 (3) | N5—N4—C22 | 121.0 (3) |
C21—C19—C12 | 128.0 (3) | C21—N5—N4 | 104.4 (3) |
N4—C20—C19 | 108.2 (3) | N8—N7—C28 | 109.4 (3) |
N4—C20—H20 | 125.9 | N7—N8—N9 | 107.0 (3) |
C19—C20—H20 | 125.9 | C29—N9—N8 | 110.7 (3) |
N5—C21—C19 | 111.7 (3) | C29—N9—C31 | 130.0 (3) |
N5—C21—C28 | 121.1 (3) | N8—N9—C31 | 119.3 (3) |
C19—C21—C28 | 127.2 (3) | C8—S1—C9 | 87.82 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···Br1i | 0.93 | 2.85 | 3.726 (4) | 157 |
Symmetry code: (i) −x−1/2, y+1/2, −z+1/2. |
Footnotes
‡Additional corresponding author, e-mail: kariukib@cardiff.ac.uk.
Funding information
The project was supported by King Saud University, Deanship of Scientific Research, Research Chairs.
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