organic compounds
4-(4-Bromophenyl)-2-(3-(4-bromophenyl)-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
In the title compound, C37H28Br2N8S, the dihedral angles between the planes of tolyl–triazolyl–pyrazolyl–phenyl rings are 47.5 (1), 11.4 (2) and 22.4 (2)°, respectively, and the angles between the bromophenyl–thiazolyl–dihydropyrazolyl–bromophenyl rings are 16.0 (2), 5.1 (2) and 0.8 (2)°, respectively. The dihedral angle between the planes of the pyrazolyl and dihydropyrazolyl rings is 67.7 (1)°. In the crystal, weak C—H⋯Br interactions form chains of molecules propagating in the [010] direction.
Keywords: crystal structure; thiazole; pyrazole; 1,2,3-triazole.
CCDC reference: 1830522
Structure description
Several synthetic procedures have been reported for the synthesis of pyrazole, thiazole and triazole-containing heterocycles (Assarzadeh et al., 2014; Hassan et al., 2014; Sarigol et al., 2015). Compounds with pyrazolylthiazole and pyrazolyltriazole ring systems show a variety of biological activities (Dawood et al., 2013; Dayakar et al., 2017; Gomha et al., 2016). The X-ray for a related compound has been recently published (Abu El-Enin et al., 2017).
The 37H28Br2N8S (Fig. 1). The molecule can be considered as two sets of rings linked by the C10—C19 bond. The dihedral angles between the planes of tolyl–triazolyl–pyrazolyl–phenyl rings are 47.5 (1), 11.4 (2) and 22.4 (2)°, respectively, in the first set. In the second set, the dihedral angles between the bromophenyl–thiazolyl–dihydropyrazolyl–bromophenyl rings are 16.0 (2), 5.1 (2) and 0.8 (2)°, respectively. The dihedral angle between the planes of the pyrazolyl and dihydropyrazolyl rings is 67.7 (1)°. In the crystal, weak C—H⋯Br interactions form chains of molecules parallel to the b-axis direction (Table 1, Fig. 2) with adjacent molecules in the chain related by the 21 screw axis.
comprises one molecule of CSynthesis and crystallization
The title compound was synthesized using a literature procedure (Abdel-Wahab et al., 2017) and colourless needles were recrystallized from dimethylformamide solution.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1830522
https://doi.org/10.1107/S2414314618004492/hb4219sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314618004492/hb4219Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314618004492/hb4219Isup3.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: SHELXL (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).C37H28Br2N8S | F(000) = 1568 |
Mr = 776.55 | Dx = 1.534 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54184 Å |
a = 10.3624 (2) Å | Cell parameters from 7424 reflections |
b = 13.5082 (3) Å | θ = 3.6–74.1° |
c = 24.0262 (6) Å | µ = 3.96 mm−1 |
β = 90.457 (2)° | T = 293 K |
V = 3363.02 (13) Å3 | Needle, colourless |
Z = 4 | 0.24 × 0.09 × 0.05 mm |
Rigaku Oxford Diffraction SuperNova, Dual, Cu at zero, Atlas diffractometer | 5247 reflections with I > 2σ(I) |
ω scans | Rint = 0.037 |
Absorption correction: gaussian (CrysAlisPro; Rigaku OD, 2015) | θmax = 74.4°, θmin = 3.7° |
Tmin = 0.971, Tmax = 0.995 | h = −11→12 |
24126 measured reflections | k = −16→16 |
6772 independent reflections | l = −29→26 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.052 | H-atom parameters constrained |
wR(F2) = 0.162 | w = 1/[σ2(Fo2) + (0.0831P)2 + 2.1716P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
6772 reflections | Δρmax = 1.06 e Å−3 |
435 parameters | Δρmin = −1.26 e Å−3 |
0 restraints |
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. All hydrogen atoms were placed in calculated positions and refined using a riding model. Aromatic C—H distances were set to 0.93 Å and their U(iso) set to 1.2 times the Ueq for the atoms to which they are bonded. Methine C—H distances were set to 0.98 Å and their U(iso) set to 1.2 times the Ueq for the atoms to which they are bonded. Methylene C—H distances were set to 0.97 Å and their U(iso) set to 1.2 times the Ueq for the atoms to which they are bonded. Methyl groups were allowed to rotate about the C—C bond and C—H distances were set to 0.96 Å with U(iso) set to 1.5 times the Ueq for the C atoms to which they are bonded. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.6973 (4) | 0.3731 (3) | 0.28057 (17) | 0.0651 (9) | |
C2 | 0.6176 (4) | 0.3335 (3) | 0.31946 (17) | 0.0641 (9) | |
H2 | 0.625004 | 0.267133 | 0.329169 | 0.077* | |
C3 | 0.5256 (3) | 0.3922 (2) | 0.34446 (16) | 0.0603 (8) | |
H3 | 0.471807 | 0.365079 | 0.371241 | 0.072* | |
C4 | 0.5127 (3) | 0.4917 (2) | 0.32994 (14) | 0.0508 (7) | |
C5 | 0.5965 (4) | 0.5294 (3) | 0.29070 (16) | 0.0637 (9) | |
H5 | 0.589857 | 0.595704 | 0.280653 | 0.076* | |
C6 | 0.6894 (4) | 0.4714 (3) | 0.26610 (18) | 0.0719 (10) | |
H6 | 0.745692 | 0.498252 | 0.240208 | 0.086* | |
C7 | 0.4122 (3) | 0.5552 (2) | 0.35431 (13) | 0.0506 (7) | |
C8 | 0.3420 (3) | 0.5346 (3) | 0.40002 (15) | 0.0610 (8) | |
H8 | 0.350841 | 0.477459 | 0.421294 | 0.073* | |
C9 | 0.2914 (3) | 0.6884 (2) | 0.35436 (13) | 0.0508 (7) | |
C10 | 0.2794 (3) | 0.8355 (2) | 0.28957 (12) | 0.0511 (7) | |
H10 | 0.371431 | 0.850916 | 0.293508 | 0.061* | |
C11 | 0.1968 (4) | 0.9295 (2) | 0.29769 (14) | 0.0572 (8) | |
H11A | 0.250633 | 0.987460 | 0.303169 | 0.069* | |
H11B | 0.139881 | 0.940552 | 0.266035 | 0.069* | |
C12 | 0.1214 (3) | 0.9060 (2) | 0.34918 (13) | 0.0494 (7) | |
C13 | 0.0284 (3) | 0.9733 (2) | 0.37463 (13) | 0.0511 (7) | |
C14 | 0.0054 (4) | 1.0665 (3) | 0.35213 (15) | 0.0623 (8) | |
H14 | 0.049303 | 1.085800 | 0.320319 | 0.075* | |
C15 | −0.0819 (4) | 1.1312 (3) | 0.37621 (17) | 0.0666 (9) | |
H15 | −0.097030 | 1.193332 | 0.360759 | 0.080* | |
C16 | −0.1455 (4) | 1.1017 (3) | 0.42334 (17) | 0.0640 (9) | |
C17 | −0.1242 (4) | 1.0100 (3) | 0.44684 (19) | 0.0750 (11) | |
H17 | −0.168056 | 0.991438 | 0.478790 | 0.090* | |
C18 | −0.0376 (4) | 0.9463 (3) | 0.42278 (18) | 0.0697 (10) | |
H18 | −0.022776 | 0.884545 | 0.438717 | 0.084* | |
C19 | 0.2525 (3) | 0.7858 (2) | 0.23482 (12) | 0.0464 (6) | |
C20 | 0.1731 (3) | 0.7073 (2) | 0.22478 (13) | 0.0489 (7) | |
H20 | 0.127363 | 0.671684 | 0.251249 | 0.059* | |
C21 | 0.2988 (3) | 0.8134 (2) | 0.18174 (13) | 0.0467 (6) | |
C22 | 0.1075 (3) | 0.6137 (2) | 0.13990 (13) | 0.0499 (7) | |
C23 | 0.0020 (4) | 0.5679 (3) | 0.16363 (14) | 0.0592 (8) | |
H23 | −0.029384 | 0.589652 | 0.197666 | 0.071* | |
C24 | −0.0560 (4) | 0.4900 (3) | 0.13649 (18) | 0.0737 (10) | |
H24 | −0.126517 | 0.458539 | 0.152406 | 0.088* | |
C25 | −0.0108 (5) | 0.4585 (3) | 0.0863 (2) | 0.0858 (13) | |
H25 | −0.050553 | 0.405750 | 0.068145 | 0.103* | |
C26 | 0.0935 (5) | 0.5048 (4) | 0.06260 (18) | 0.0814 (12) | |
H26 | 0.123955 | 0.483029 | 0.028413 | 0.098* | |
C27 | 0.1535 (4) | 0.5832 (3) | 0.08898 (15) | 0.0629 (8) | |
H27 | 0.223532 | 0.614806 | 0.072782 | 0.075* | |
C28 | 0.3889 (3) | 0.8933 (2) | 0.16866 (13) | 0.0484 (6) | |
C29 | 0.4572 (3) | 0.9133 (2) | 0.12084 (13) | 0.0478 (6) | |
C30 | 0.4513 (4) | 0.8675 (3) | 0.06460 (14) | 0.0604 (8) | |
H30A | 0.450006 | 0.918545 | 0.036809 | 0.091* | |
H30B | 0.374530 | 0.828110 | 0.061299 | 0.091* | |
H30C | 0.525694 | 0.826229 | 0.059384 | 0.091* | |
C31 | 0.6254 (3) | 1.0440 (2) | 0.10339 (13) | 0.0491 (7) | |
C32 | 0.6289 (4) | 1.1467 (3) | 0.10291 (18) | 0.0670 (9) | |
H32 | 0.566534 | 1.183148 | 0.121488 | 0.080* | |
C33 | 0.7265 (4) | 1.1939 (3) | 0.07445 (19) | 0.0688 (10) | |
H33 | 0.729841 | 1.262673 | 0.074715 | 0.083* | |
C34 | 0.8197 (3) | 1.1416 (3) | 0.04547 (15) | 0.0561 (7) | |
C35 | 0.8135 (3) | 1.0398 (3) | 0.04709 (14) | 0.0549 (7) | |
H35 | 0.875406 | 1.003122 | 0.028335 | 0.066* | |
C36 | 0.7179 (3) | 0.9905 (2) | 0.07575 (14) | 0.0535 (7) | |
H36 | 0.716152 | 0.921723 | 0.076350 | 0.064* | |
C37 | 0.9254 (4) | 1.1942 (3) | 0.0147 (2) | 0.0761 (11) | |
H37A | 0.959317 | 1.151361 | −0.013472 | 0.114* | |
H37B | 0.993050 | 1.211934 | 0.040364 | 0.114* | |
H37C | 0.891225 | 1.253011 | −0.002358 | 0.114* | |
N1 | 0.3837 (3) | 0.6446 (2) | 0.32804 (11) | 0.0524 (6) | |
N2 | 0.2349 (3) | 0.7741 (2) | 0.33681 (11) | 0.0565 (6) | |
N3 | 0.1453 (3) | 0.8199 (2) | 0.36979 (11) | 0.0523 (6) | |
N4 | 0.1729 (3) | 0.69057 (18) | 0.16912 (11) | 0.0493 (6) | |
N5 | 0.2502 (3) | 0.75534 (19) | 0.14154 (10) | 0.0494 (6) | |
N6 | 0.4192 (3) | 0.9628 (2) | 0.20785 (12) | 0.0593 (7) | |
N7 | 0.5043 (3) | 1.0237 (2) | 0.18751 (12) | 0.0601 (7) | |
N8 | 0.5289 (3) | 0.9938 (2) | 0.13477 (11) | 0.0512 (6) | |
S1 | 0.23386 (9) | 0.62837 (7) | 0.41369 (4) | 0.0613 (2) | |
Br1 | 0.82136 (6) | 0.29156 (4) | 0.24450 (3) | 0.1019 (2) | |
Br2 | −0.26346 (5) | 1.19038 (3) | 0.45748 (3) | 0.0937 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.071 (2) | 0.0499 (18) | 0.074 (2) | 0.0077 (16) | 0.0066 (18) | −0.0076 (16) |
C2 | 0.072 (2) | 0.0374 (15) | 0.083 (2) | −0.0004 (15) | 0.0010 (18) | 0.0030 (16) |
C3 | 0.0609 (19) | 0.0454 (17) | 0.075 (2) | −0.0050 (14) | 0.0041 (16) | 0.0091 (15) |
C4 | 0.0540 (16) | 0.0436 (15) | 0.0548 (17) | −0.0027 (13) | −0.0007 (13) | −0.0002 (13) |
C5 | 0.074 (2) | 0.0402 (16) | 0.077 (2) | 0.0030 (15) | 0.0170 (18) | 0.0095 (15) |
C6 | 0.079 (2) | 0.054 (2) | 0.083 (3) | 0.0086 (17) | 0.025 (2) | 0.0130 (18) |
C7 | 0.0528 (16) | 0.0455 (15) | 0.0534 (16) | −0.0032 (13) | −0.0014 (13) | 0.0021 (13) |
C8 | 0.0598 (19) | 0.059 (2) | 0.064 (2) | 0.0047 (15) | 0.0045 (15) | 0.0129 (16) |
C9 | 0.0573 (17) | 0.0481 (16) | 0.0471 (16) | −0.0010 (13) | 0.0006 (13) | 0.0000 (13) |
C10 | 0.0636 (18) | 0.0440 (15) | 0.0458 (15) | −0.0014 (13) | 0.0064 (13) | −0.0039 (12) |
C11 | 0.072 (2) | 0.0435 (16) | 0.0559 (18) | 0.0006 (14) | 0.0141 (15) | −0.0061 (13) |
C12 | 0.0506 (15) | 0.0467 (16) | 0.0511 (16) | −0.0027 (13) | 0.0030 (12) | −0.0041 (13) |
C13 | 0.0513 (16) | 0.0478 (16) | 0.0543 (16) | −0.0018 (13) | 0.0050 (13) | −0.0036 (13) |
C14 | 0.079 (2) | 0.0512 (18) | 0.0568 (18) | 0.0013 (16) | 0.0120 (16) | −0.0010 (15) |
C15 | 0.083 (2) | 0.0461 (18) | 0.071 (2) | 0.0080 (16) | 0.0106 (19) | 0.0006 (16) |
C16 | 0.062 (2) | 0.0521 (18) | 0.078 (2) | 0.0020 (15) | 0.0119 (17) | −0.0082 (17) |
C17 | 0.073 (2) | 0.067 (2) | 0.085 (3) | 0.0066 (19) | 0.033 (2) | 0.009 (2) |
C18 | 0.071 (2) | 0.056 (2) | 0.083 (2) | 0.0093 (17) | 0.0233 (19) | 0.0087 (18) |
C19 | 0.0507 (15) | 0.0411 (14) | 0.0474 (15) | 0.0025 (12) | 0.0070 (12) | −0.0024 (12) |
C20 | 0.0580 (17) | 0.0432 (15) | 0.0456 (15) | −0.0022 (12) | 0.0091 (12) | 0.0002 (12) |
C21 | 0.0478 (15) | 0.0416 (15) | 0.0508 (15) | 0.0018 (11) | 0.0078 (12) | −0.0006 (12) |
C22 | 0.0572 (17) | 0.0418 (15) | 0.0508 (16) | −0.0011 (12) | −0.0001 (13) | −0.0023 (12) |
C23 | 0.072 (2) | 0.0521 (18) | 0.0542 (18) | −0.0113 (15) | 0.0042 (15) | −0.0009 (14) |
C24 | 0.086 (3) | 0.061 (2) | 0.075 (2) | −0.0232 (19) | 0.004 (2) | 0.0020 (18) |
C25 | 0.101 (3) | 0.069 (3) | 0.087 (3) | −0.024 (2) | 0.000 (2) | −0.026 (2) |
C26 | 0.092 (3) | 0.083 (3) | 0.069 (2) | −0.009 (2) | 0.011 (2) | −0.031 (2) |
C27 | 0.064 (2) | 0.066 (2) | 0.0593 (19) | −0.0034 (16) | 0.0058 (15) | −0.0120 (16) |
C28 | 0.0496 (15) | 0.0463 (15) | 0.0494 (15) | −0.0028 (12) | 0.0071 (12) | −0.0029 (12) |
C29 | 0.0485 (15) | 0.0430 (15) | 0.0521 (16) | −0.0023 (12) | 0.0059 (12) | −0.0021 (12) |
C30 | 0.067 (2) | 0.062 (2) | 0.0517 (17) | −0.0124 (16) | 0.0086 (15) | −0.0056 (15) |
C31 | 0.0498 (15) | 0.0452 (15) | 0.0525 (16) | −0.0047 (12) | 0.0049 (12) | −0.0005 (13) |
C32 | 0.062 (2) | 0.0477 (18) | 0.092 (3) | −0.0034 (15) | 0.0217 (18) | −0.0099 (17) |
C33 | 0.068 (2) | 0.0410 (17) | 0.098 (3) | −0.0050 (15) | 0.017 (2) | −0.0012 (17) |
C34 | 0.0547 (17) | 0.0520 (18) | 0.0618 (19) | −0.0070 (14) | 0.0046 (14) | 0.0020 (14) |
C35 | 0.0553 (17) | 0.0521 (17) | 0.0575 (18) | 0.0020 (14) | 0.0112 (14) | 0.0009 (14) |
C36 | 0.0575 (17) | 0.0427 (15) | 0.0603 (18) | 0.0027 (13) | 0.0053 (14) | 0.0034 (13) |
C37 | 0.071 (2) | 0.059 (2) | 0.099 (3) | −0.0102 (17) | 0.023 (2) | 0.009 (2) |
N1 | 0.0606 (15) | 0.0463 (14) | 0.0505 (14) | 0.0031 (11) | 0.0052 (11) | 0.0009 (11) |
N2 | 0.0691 (16) | 0.0521 (15) | 0.0485 (14) | 0.0103 (13) | 0.0123 (12) | 0.0019 (12) |
N3 | 0.0565 (14) | 0.0516 (14) | 0.0490 (13) | 0.0035 (11) | 0.0101 (11) | −0.0008 (11) |
N4 | 0.0582 (14) | 0.0416 (13) | 0.0480 (13) | −0.0037 (10) | 0.0057 (11) | −0.0017 (10) |
N5 | 0.0551 (14) | 0.0455 (13) | 0.0478 (13) | −0.0040 (11) | 0.0101 (11) | −0.0017 (11) |
N6 | 0.0642 (16) | 0.0563 (16) | 0.0576 (15) | −0.0105 (13) | 0.0155 (13) | −0.0111 (13) |
N7 | 0.0653 (16) | 0.0559 (16) | 0.0593 (16) | −0.0120 (13) | 0.0146 (13) | −0.0115 (13) |
N8 | 0.0531 (14) | 0.0477 (14) | 0.0529 (14) | −0.0059 (11) | 0.0082 (11) | −0.0039 (11) |
S1 | 0.0628 (5) | 0.0643 (5) | 0.0571 (5) | 0.0053 (4) | 0.0110 (4) | 0.0088 (4) |
Br1 | 0.1222 (5) | 0.0676 (3) | 0.1165 (4) | 0.0333 (3) | 0.0368 (3) | 0.0011 (3) |
Br2 | 0.1003 (4) | 0.0578 (3) | 0.1239 (4) | 0.0151 (2) | 0.0496 (3) | −0.0028 (2) |
C1—C2 | 1.361 (6) | C20—H20 | 0.9300 |
C1—C6 | 1.376 (5) | C21—N5 | 1.339 (4) |
C1—Br1 | 1.906 (4) | C21—C28 | 1.463 (4) |
C2—C3 | 1.380 (5) | C22—C27 | 1.380 (5) |
C2—H2 | 0.9300 | C22—C23 | 1.383 (5) |
C3—C4 | 1.395 (5) | C22—N4 | 1.422 (4) |
C3—H3 | 0.9300 | C23—C24 | 1.374 (5) |
C4—C5 | 1.384 (5) | C23—H23 | 0.9300 |
C4—C7 | 1.474 (5) | C24—C25 | 1.365 (6) |
C5—C6 | 1.378 (5) | C24—H24 | 0.9300 |
C5—H5 | 0.9300 | C25—C26 | 1.377 (6) |
C6—H6 | 0.9300 | C25—H25 | 0.9300 |
C7—C8 | 1.351 (5) | C26—C27 | 1.379 (5) |
C7—N1 | 1.394 (4) | C26—H26 | 0.9300 |
C8—S1 | 1.725 (4) | C27—H27 | 0.9300 |
C8—H8 | 0.9300 | C28—N6 | 1.365 (4) |
C9—N1 | 1.294 (4) | C28—C29 | 1.381 (4) |
C9—N2 | 1.362 (4) | C29—N8 | 1.358 (4) |
C9—S1 | 1.749 (3) | C29—C30 | 1.487 (4) |
C10—N2 | 1.482 (4) | C30—H30A | 0.9600 |
C10—C19 | 1.501 (4) | C30—H30B | 0.9600 |
C10—C11 | 1.545 (4) | C30—H30C | 0.9600 |
C10—H10 | 0.9800 | C31—C36 | 1.376 (4) |
C11—C12 | 1.503 (4) | C31—C32 | 1.387 (5) |
C11—H11A | 0.9700 | C31—N8 | 1.428 (4) |
C11—H11B | 0.9700 | C32—C33 | 1.381 (5) |
C12—N3 | 1.286 (4) | C32—H32 | 0.9300 |
C12—C13 | 1.462 (4) | C33—C34 | 1.388 (5) |
C13—C14 | 1.390 (5) | C33—H33 | 0.9300 |
C13—C18 | 1.397 (5) | C34—C35 | 1.377 (5) |
C14—C15 | 1.388 (5) | C34—C37 | 1.505 (5) |
C14—H14 | 0.9300 | C35—C36 | 1.381 (5) |
C15—C16 | 1.374 (5) | C35—H35 | 0.9300 |
C15—H15 | 0.9300 | C36—H36 | 0.9300 |
C16—C17 | 1.378 (6) | C37—H37A | 0.9600 |
C16—Br2 | 1.902 (4) | C37—H37B | 0.9600 |
C17—C18 | 1.374 (5) | C37—H37C | 0.9600 |
C17—H17 | 0.9300 | N2—N3 | 1.373 (4) |
C18—H18 | 0.9300 | N4—N5 | 1.362 (4) |
C19—C20 | 1.363 (4) | N6—N7 | 1.304 (4) |
C19—C21 | 1.416 (4) | N7—N8 | 1.356 (4) |
C20—N4 | 1.356 (4) | ||
C2—C1—C6 | 121.1 (3) | C27—C22—C23 | 120.8 (3) |
C2—C1—Br1 | 120.1 (3) | C27—C22—N4 | 119.3 (3) |
C6—C1—Br1 | 118.8 (3) | C23—C22—N4 | 119.9 (3) |
C1—C2—C3 | 119.9 (3) | C24—C23—C22 | 119.4 (3) |
C1—C2—H2 | 120.0 | C24—C23—H23 | 120.3 |
C3—C2—H2 | 120.0 | C22—C23—H23 | 120.3 |
C2—C3—C4 | 120.6 (3) | C25—C24—C23 | 120.4 (4) |
C2—C3—H3 | 119.7 | C25—C24—H24 | 119.8 |
C4—C3—H3 | 119.7 | C23—C24—H24 | 119.8 |
C5—C4—C3 | 117.8 (3) | C24—C25—C26 | 120.0 (4) |
C5—C4—C7 | 120.3 (3) | C24—C25—H25 | 120.0 |
C3—C4—C7 | 121.9 (3) | C26—C25—H25 | 120.0 |
C6—C5—C4 | 121.8 (3) | C25—C26—C27 | 120.7 (4) |
C6—C5—H5 | 119.1 | C25—C26—H26 | 119.6 |
C4—C5—H5 | 119.1 | C27—C26—H26 | 119.6 |
C1—C6—C5 | 118.8 (4) | C26—C27—C22 | 118.6 (4) |
C1—C6—H6 | 120.6 | C26—C27—H27 | 120.7 |
C5—C6—H6 | 120.6 | C22—C27—H27 | 120.7 |
C8—C7—N1 | 115.6 (3) | N6—C28—C29 | 108.8 (3) |
C8—C7—C4 | 126.1 (3) | N6—C28—C21 | 120.2 (3) |
N1—C7—C4 | 118.2 (3) | C29—C28—C21 | 130.9 (3) |
C7—C8—S1 | 111.0 (3) | N8—C29—C28 | 103.6 (3) |
C7—C8—H8 | 124.5 | N8—C29—C30 | 125.1 (3) |
S1—C8—H8 | 124.5 | C28—C29—C30 | 131.1 (3) |
N1—C9—N2 | 123.7 (3) | C29—C30—H30A | 109.5 |
N1—C9—S1 | 116.4 (2) | C29—C30—H30B | 109.5 |
N2—C9—S1 | 119.9 (2) | H30A—C30—H30B | 109.5 |
N2—C10—C19 | 111.3 (3) | C29—C30—H30C | 109.5 |
N2—C10—C11 | 100.8 (2) | H30A—C30—H30C | 109.5 |
C19—C10—C11 | 112.3 (3) | H30B—C30—H30C | 109.5 |
N2—C10—H10 | 110.7 | C36—C31—C32 | 120.1 (3) |
C19—C10—H10 | 110.7 | C36—C31—N8 | 120.0 (3) |
C11—C10—H10 | 110.7 | C32—C31—N8 | 119.8 (3) |
C12—C11—C10 | 102.8 (3) | C33—C32—C31 | 119.0 (3) |
C12—C11—H11A | 111.2 | C33—C32—H32 | 120.5 |
C10—C11—H11A | 111.2 | C31—C32—H32 | 120.5 |
C12—C11—H11B | 111.2 | C32—C33—C34 | 121.9 (3) |
C10—C11—H11B | 111.2 | C32—C33—H33 | 119.1 |
H11A—C11—H11B | 109.1 | C34—C33—H33 | 119.1 |
N3—C12—C13 | 121.8 (3) | C35—C34—C33 | 117.4 (3) |
N3—C12—C11 | 114.1 (3) | C35—C34—C37 | 121.3 (3) |
C13—C12—C11 | 124.1 (3) | C33—C34—C37 | 121.2 (3) |
C14—C13—C18 | 118.4 (3) | C34—C35—C36 | 121.9 (3) |
C14—C13—C12 | 120.8 (3) | C34—C35—H35 | 119.0 |
C18—C13—C12 | 120.8 (3) | C36—C35—H35 | 119.0 |
C15—C14—C13 | 121.3 (3) | C31—C36—C35 | 119.6 (3) |
C15—C14—H14 | 119.4 | C31—C36—H36 | 120.2 |
C13—C14—H14 | 119.4 | C35—C36—H36 | 120.2 |
C16—C15—C14 | 118.6 (3) | C34—C37—H37A | 109.5 |
C16—C15—H15 | 120.7 | C34—C37—H37B | 109.5 |
C14—C15—H15 | 120.7 | H37A—C37—H37B | 109.5 |
C15—C16—C17 | 121.5 (3) | C34—C37—H37C | 109.5 |
C15—C16—Br2 | 119.1 (3) | H37A—C37—H37C | 109.5 |
C17—C16—Br2 | 119.4 (3) | H37B—C37—H37C | 109.5 |
C18—C17—C16 | 119.6 (4) | C9—N1—C7 | 109.3 (3) |
C18—C17—H17 | 120.2 | C9—N2—N3 | 119.7 (3) |
C16—C17—H17 | 120.2 | C9—N2—C10 | 125.2 (3) |
C17—C18—C13 | 120.7 (4) | N3—N2—C10 | 113.9 (3) |
C17—C18—H18 | 119.7 | C12—N3—N2 | 108.3 (3) |
C13—C18—H18 | 119.7 | C20—N4—N5 | 112.1 (2) |
C20—C19—C21 | 104.7 (3) | C20—N4—C22 | 127.2 (3) |
C20—C19—C10 | 127.6 (3) | N5—N4—C22 | 120.6 (3) |
C21—C19—C10 | 127.6 (3) | C21—N5—N4 | 104.1 (2) |
N4—C20—C19 | 107.5 (3) | N7—N6—C28 | 109.2 (3) |
N4—C20—H20 | 126.3 | N6—N7—N8 | 107.1 (3) |
C19—C20—H20 | 126.3 | N7—N8—C29 | 111.3 (3) |
N5—C21—C19 | 111.5 (3) | N7—N8—C31 | 119.3 (3) |
N5—C21—C28 | 120.9 (3) | C29—N8—C31 | 129.4 (3) |
C19—C21—C28 | 127.5 (3) | C8—S1—C9 | 87.66 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···Br1i | 0.93 | 2.87 | 3.741 (3) | 157 |
Symmetry code: (i) −x+3/2, 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.
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