organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2414-3146

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

Edited by D.-J. Xu, Zhejiang University (Yuquan Campus), China (Received 23 December 2017; accepted 6 January 2018; online 12 January 2018)

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, ππ and C—H⋯Br inter­actions link the mol­ecules to form columns parallel to [010]. The ππ inter­actions involve partially overlapping nonparallel bromo­phenyl and tolyl groups.

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

Various procedures have been reported for the synthesis of heterocycles containing the pyrazolinyl­thia­zole moiety (Abdel-Wahab et al., 2009[Abdel-Wahab, B. F., Abdel-Aziz, H. A. & Ahmed, E. M. (2009). Eur. J. Med. Chem. 44, 2632-2635.]; Abid & Azam, 2006[Abid, M. & Azam, A. (2006). Bioorg. Med. Chem. Lett. 16, 2812-2816.]; Bonacorso et al., 2002[Bonacorso, H. G., Wastowski, A. D., Muniz, M. N., Zanatta, N. & Martins, A. P. (2002). Synthesis, pp. 1079-1083.]). Both pyrazolyltriazoles and 1-thia­zol-2-ylpyrazolines show various anti­microbial (Abdel-Wahab et al., 2012[Abdel-Wahab, B. F., Abdel-Latif, E., Mohamed, H. A. & Awad, G. E. A. (2012). Eur. J. Med. Chem. 52, 263-268.], 2017[Abdel-Wahab, B. F., Khidre, R. E., Mohamed, H. A. & El-Hiti, G. A. (2017). Arab. J. Sci. Eng. 42, 2441-2448.]), anti­tumor and anti­mycobacterial activities (Kumar et al., 2003[Kumar, A., Husain, M., Prasad, A. K., Singh, I., Vats, A., Sharma, N. K., Sharma, S. K., Gupta, R. K., Olsen, C. E., Bracke, M. E., Gross, R. A. & Parmar, V. S. (2003). Indian J. Chem. 42B, 1950-1957.]).

The asymmetric unit comprises a single mol­ecule of C37H28BrClN8O (Fig. 1[link]). Contact between neighbouring mol­ecules includes ππ and C—H⋯Br inter­actions (Table 1[link], Fig. 2[link]) to form columns parallel to [010]. The ππ 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°.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C2—H2⋯Br1i 0.93 2.85 3.726 (4) 157
Symmetry code: (i) [-x-{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].
[Figure 1]
Figure 1
An ORTEP representation of the title mol­ecule showing 50% probability ellipsoids.
[Figure 2]
Figure 2
Part of the crystal structure showing inter­molecular inter­actions as dotted lines.

Synthesis 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[Abdel-Wahab, B. F., Khidre, R. E., Mohamed, H. A. & El-Hiti, G. A. (2017). Arab. J. Sci. Eng. 42, 2441-2448.]) were obtained by recrystallization of the crude product obtained following work-up using di­methyl­formamide as the solvent.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link].

Table 2
Experimental details

Crystal data
Chemical formula C37H28BrClN8S
Mr 732.09
Crystal system, space group Monoclinic, P21/n
Temperature (K) 296
a, b, c (Å) 10.4220 (7), 13.4232 (5), 23.8943 (14)
β (°) 90.198 (6)
V3) 3342.7 (3)
Z 4
Radiation type Mo Kα
μ (mm−1) 1.41
Crystal size (mm) 0.42 × 0.10 × 0.04
 
Data collection
Diffractometer Agilent SuperNova, Dual, Cu at zero, Atlas
Absorption correction Gaussian (CrysAlis PRO; Agilent, 2014[Agilent (2014). CrysAlis PRO. Agilent Technologies, Yarnton, England.])
Tmin, Tmax 0.794, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections 15250, 7792, 3958
Rint 0.039
(sin θ/λ)max−1) 0.702
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.063, 0.183, 1.03
No. of reflections 7792
No. of parameters 435
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.77, −0.95
Computer programs: CrysAlis PRO (Agilent, 2014[Agilent (2014). CrysAlis PRO. Agilent Technologies, Yarnton, England.]), SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL2013 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), ORTEP-3 for Windows and WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and CHEMDRAW Ultra (Cambridge Soft, 2001[Cambridge Soft (2001). CHEMDRAW Ultra. Cambridge Soft Corporation, Cambridge, Massachusetts, USA.]).

Structural data


Computing details top

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: 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).

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 top
Crystal data top
C37H28BrClN8SF(000) = 1496
Mr = 732.09Dx = 1.455 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 10.4220 (7) ÅCell parameters from 2941 reflections
b = 13.4232 (5) Åθ = 3.5–23.9°
c = 23.8943 (14) ŵ = 1.41 mm1
β = 90.198 (6)°T = 296 K
V = 3342.7 (3) Å3Needle, colourless
Z = 40.42 × 0.10 × 0.04 mm
Data collection top
Agilent SuperNova, Dual, Cu at zero, Atlas
diffractometer
3958 reflections with I > 2σ(I)
ω scansRint = 0.039
Absorption correction: gaussian
(CrysAlis PRO; Agilent, 2014)
θmax = 29.9°, θmin = 3.0°
Tmin = 0.794, Tmax = 1.000h = 1313
15250 measured reflectionsk = 1813
7792 independent reflectionsl = 3224
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.063H-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 reflectionsΔρmax = 0.77 e Å3
435 parametersΔρmin = 0.95 e Å3
Special details top

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).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.0099 (4)0.4942 (3)0.33097 (16)0.0498 (9)
C20.0953 (4)0.5332 (3)0.29246 (18)0.0607 (11)
H20.09010.60030.28310.073*
C30.1882 (4)0.4747 (3)0.26767 (19)0.0688 (12)
H30.24510.50220.24190.083*
C40.1960 (4)0.3762 (3)0.28134 (19)0.0623 (11)
C50.1140 (4)0.3358 (3)0.3204 (2)0.0648 (12)
H50.12090.26890.33000.078*
C60.0220 (4)0.3943 (3)0.34518 (18)0.0581 (11)
H60.03280.36680.37180.070*
C70.0919 (4)0.5579 (3)0.35531 (16)0.0491 (9)
C80.1620 (4)0.5379 (3)0.40160 (18)0.0597 (11)
H80.15270.48100.42340.072*
C90.2136 (4)0.6910 (3)0.35524 (15)0.0482 (9)
C100.3825 (4)0.9098 (3)0.34920 (16)0.0474 (9)
C110.3075 (4)0.9318 (3)0.29734 (16)0.0568 (11)
H11A0.36380.94220.26570.068*
H11B0.25420.99030.30220.068*
C120.2252 (4)0.8382 (3)0.28926 (15)0.0487 (9)
H120.13400.85440.29310.058*
C130.4759 (4)0.9774 (3)0.37459 (16)0.0501 (9)
C140.5408 (4)0.9515 (3)0.4233 (2)0.0715 (13)
H140.52520.88990.43990.086*
C150.6282 (5)1.0159 (3)0.4476 (2)0.0831 (15)
H150.67130.99780.48020.100*
C160.6511 (4)1.1068 (3)0.4232 (2)0.0659 (12)
C170.5883 (5)1.1349 (3)0.37556 (19)0.0679 (12)
H170.60471.19660.35930.082*
C180.4996 (4)1.0703 (3)0.35153 (18)0.0611 (11)
H180.45551.08980.31950.073*
C190.2493 (4)0.7877 (2)0.23490 (15)0.0440 (8)
C200.3277 (4)0.7084 (2)0.22460 (15)0.0471 (9)
H200.37400.67280.25130.057*
C210.2008 (4)0.8139 (2)0.18121 (15)0.0449 (9)
C220.3920 (4)0.6132 (2)0.13991 (15)0.0469 (9)
C230.3448 (4)0.5813 (3)0.08881 (17)0.0611 (11)
H230.27390.61210.07260.073*
C240.4049 (5)0.5027 (4)0.0624 (2)0.0838 (15)
H240.37430.48000.02810.101*
C250.5106 (5)0.4577 (4)0.0869 (2)0.0829 (15)
H250.55010.40430.06910.099*
C260.5570 (5)0.4910 (3)0.1368 (2)0.0729 (13)
H260.62860.46090.15280.087*
C270.4981 (4)0.5691 (3)0.16364 (17)0.0568 (10)
H270.52990.59190.19770.068*
C280.1107 (4)0.8942 (3)0.16787 (15)0.0456 (9)
C290.0411 (4)0.9133 (3)0.12035 (15)0.0457 (9)
C300.0442 (4)0.8669 (3)0.06355 (16)0.0575 (10)
H30A0.03210.82800.05790.086*
H30B0.11820.82470.06060.086*
H30C0.04830.91830.03570.086*
C310.1280 (4)1.0448 (3)0.10234 (15)0.0468 (9)
C320.1308 (4)1.1480 (3)0.10141 (19)0.0610 (11)
H320.06771.18480.11970.073*
C330.2283 (4)1.1950 (3)0.0731 (2)0.0637 (12)
H330.23051.26420.07290.076*
C340.3234 (4)1.1431 (3)0.04488 (16)0.0522 (9)
C350.3173 (4)1.0401 (3)0.04686 (16)0.0509 (9)
H350.37991.00290.02850.061*
C360.2212 (4)0.9914 (3)0.07533 (16)0.0496 (9)
H360.21950.92220.07620.060*
C370.4290 (4)1.1953 (3)0.0139 (2)0.0728 (13)
H37A0.49401.21580.03980.109*
H37B0.46571.15090.01330.109*
H37C0.39491.25280.00480.109*
N10.1209 (3)0.6470 (2)0.32887 (13)0.0504 (8)
N20.2693 (3)0.7769 (2)0.33713 (13)0.0543 (8)
N30.3588 (3)0.8233 (2)0.37024 (13)0.0518 (8)
N40.3263 (3)0.6905 (2)0.16892 (12)0.0453 (7)
N50.2478 (3)0.7548 (2)0.14118 (12)0.0476 (7)
N70.0817 (3)0.9641 (2)0.20710 (13)0.0566 (8)
N80.0038 (3)1.0250 (2)0.18692 (14)0.0565 (8)
N90.0303 (3)0.9945 (2)0.13380 (13)0.0475 (7)
Cl10.76129 (15)1.18779 (9)0.45379 (7)0.1031 (5)
S10.27060 (11)0.63119 (8)0.41492 (5)0.0611 (3)
Br10.31987 (7)0.29441 (4)0.24515 (3)0.1046 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.053 (2)0.0446 (19)0.052 (2)0.0050 (17)0.0076 (19)0.0015 (17)
C20.068 (3)0.044 (2)0.070 (3)0.0030 (19)0.008 (2)0.011 (2)
C30.077 (3)0.053 (2)0.075 (3)0.008 (2)0.022 (3)0.011 (2)
C40.069 (3)0.046 (2)0.072 (3)0.0075 (19)0.000 (2)0.000 (2)
C50.070 (3)0.0405 (19)0.084 (3)0.000 (2)0.003 (3)0.003 (2)
C60.056 (3)0.050 (2)0.069 (3)0.0066 (19)0.005 (2)0.010 (2)
C70.049 (2)0.0468 (19)0.051 (2)0.0057 (17)0.0093 (19)0.0021 (17)
C80.061 (3)0.061 (2)0.058 (3)0.004 (2)0.001 (2)0.016 (2)
C90.053 (3)0.051 (2)0.041 (2)0.0031 (18)0.0031 (19)0.0026 (17)
C100.048 (2)0.0457 (19)0.048 (2)0.0051 (17)0.0010 (18)0.0052 (17)
C110.082 (3)0.0433 (19)0.045 (2)0.0012 (19)0.008 (2)0.0041 (17)
C120.058 (2)0.0469 (19)0.041 (2)0.0005 (17)0.0014 (18)0.0009 (16)
C130.053 (2)0.048 (2)0.049 (2)0.0027 (17)0.0001 (19)0.0025 (17)
C140.072 (3)0.060 (2)0.083 (3)0.008 (2)0.023 (3)0.014 (2)
C150.078 (4)0.075 (3)0.096 (4)0.007 (3)0.038 (3)0.011 (3)
C160.058 (3)0.059 (2)0.081 (3)0.005 (2)0.013 (2)0.005 (2)
C170.083 (3)0.049 (2)0.071 (3)0.006 (2)0.002 (3)0.002 (2)
C180.076 (3)0.051 (2)0.056 (2)0.001 (2)0.008 (2)0.0019 (19)
C190.050 (2)0.0399 (17)0.042 (2)0.0033 (16)0.0040 (17)0.0016 (15)
C200.059 (3)0.0429 (19)0.039 (2)0.0002 (17)0.0070 (18)0.0001 (15)
C210.046 (2)0.0449 (18)0.044 (2)0.0017 (16)0.0061 (17)0.0042 (16)
C220.052 (2)0.0425 (18)0.046 (2)0.0005 (17)0.0034 (18)0.0008 (16)
C230.061 (3)0.070 (3)0.052 (2)0.004 (2)0.006 (2)0.014 (2)
C240.092 (4)0.097 (3)0.063 (3)0.013 (3)0.014 (3)0.035 (3)
C250.096 (4)0.074 (3)0.079 (4)0.026 (3)0.003 (3)0.021 (3)
C260.088 (4)0.067 (3)0.063 (3)0.025 (2)0.002 (3)0.006 (2)
C270.066 (3)0.054 (2)0.050 (2)0.008 (2)0.006 (2)0.0020 (19)
C280.046 (2)0.0460 (18)0.044 (2)0.0007 (16)0.0041 (17)0.0040 (16)
C290.047 (2)0.0441 (18)0.046 (2)0.0012 (16)0.0046 (18)0.0011 (16)
C300.067 (3)0.062 (2)0.044 (2)0.009 (2)0.004 (2)0.0053 (19)
C310.048 (2)0.0485 (19)0.044 (2)0.0026 (17)0.0044 (18)0.0001 (17)
C320.055 (3)0.049 (2)0.079 (3)0.0033 (19)0.019 (2)0.009 (2)
C330.064 (3)0.041 (2)0.085 (3)0.0061 (19)0.009 (2)0.002 (2)
C340.051 (2)0.052 (2)0.054 (2)0.0030 (18)0.0045 (19)0.0001 (18)
C350.051 (2)0.051 (2)0.051 (2)0.0030 (18)0.0098 (19)0.0009 (18)
C360.053 (2)0.0419 (18)0.054 (2)0.0043 (17)0.0038 (19)0.0031 (17)
C370.068 (3)0.061 (3)0.089 (3)0.012 (2)0.022 (3)0.003 (2)
N10.061 (2)0.0459 (16)0.0442 (18)0.0017 (15)0.0005 (16)0.0034 (14)
N20.068 (2)0.0512 (17)0.0442 (18)0.0110 (16)0.0103 (17)0.0055 (15)
N30.057 (2)0.0542 (18)0.0445 (18)0.0003 (15)0.0053 (16)0.0008 (15)
N40.053 (2)0.0412 (15)0.0418 (17)0.0041 (13)0.0021 (15)0.0017 (13)
N50.054 (2)0.0466 (16)0.0424 (17)0.0032 (14)0.0062 (15)0.0001 (14)
N70.061 (2)0.0561 (18)0.053 (2)0.0097 (16)0.0135 (17)0.0093 (16)
N80.060 (2)0.0588 (19)0.051 (2)0.0098 (16)0.0119 (16)0.0110 (16)
N90.0463 (19)0.0486 (16)0.0476 (18)0.0028 (14)0.0072 (15)0.0050 (14)
Cl10.1052 (12)0.0701 (7)0.1337 (13)0.0203 (7)0.0471 (10)0.0058 (8)
S10.0605 (7)0.0698 (6)0.0529 (6)0.0044 (5)0.0073 (5)0.0115 (5)
Br10.1295 (6)0.0716 (3)0.1125 (5)0.0373 (3)0.0330 (4)0.0029 (3)
Geometric parameters (Å, º) top
C1—C21.381 (5)C20—H200.9300
C1—C61.389 (5)C21—N51.336 (4)
C1—C71.481 (5)C21—C281.464 (5)
C2—C31.378 (6)C22—C271.375 (5)
C2—H20.9300C22—C231.383 (5)
C3—C41.365 (6)C22—N41.424 (4)
C3—H30.9300C23—C241.380 (6)
C4—C51.375 (6)C23—H230.9300
C4—Br11.900 (4)C24—C251.384 (6)
C5—C61.372 (6)C24—H240.9300
C5—H50.9300C25—C261.361 (6)
C6—H60.9300C25—H250.9300
C7—C81.351 (5)C26—C271.374 (6)
C7—N11.386 (5)C26—H260.9300
C8—S11.717 (4)C27—H270.9300
C8—H80.9300C28—N71.361 (4)
C9—N11.295 (5)C28—C291.370 (5)
C9—N21.362 (5)C29—N91.360 (4)
C9—S11.739 (4)C29—C301.493 (5)
C10—N31.289 (5)C30—H30A0.9600
C10—C131.461 (5)C30—H30B0.9600
C10—C111.493 (5)C30—H30C0.9600
C11—C121.532 (5)C31—C361.367 (5)
C11—H11A0.9700C31—C321.385 (5)
C11—H11B0.9700C31—N91.433 (5)
C12—N21.481 (5)C32—C331.372 (6)
C12—C191.487 (5)C32—H320.9300
C12—H120.9800C33—C341.385 (6)
C13—C181.387 (5)C33—H330.9300
C13—C141.389 (6)C34—C351.386 (5)
C14—C151.382 (6)C34—C371.499 (5)
C14—H140.9300C35—C361.374 (5)
C15—C161.373 (6)C35—H350.9300
C15—H150.9300C36—H360.9300
C16—C171.365 (6)C37—H37A0.9600
C16—Cl11.740 (4)C37—H37B0.9600
C17—C181.390 (6)C37—H37C0.9600
C17—H170.9300N2—N31.371 (4)
C18—H180.9300N4—N51.361 (4)
C19—C201.365 (5)N7—N81.302 (4)
C19—C211.421 (5)N8—N91.361 (4)
C20—N41.352 (4)
C2—C1—C6118.0 (4)C27—C22—C23120.9 (4)
C2—C1—C7120.1 (3)C27—C22—N4120.0 (3)
C6—C1—C7121.9 (4)C23—C22—N4119.0 (4)
C3—C2—C1121.4 (4)C24—C23—C22118.7 (4)
C3—C2—H2119.3C24—C23—H23120.7
C1—C2—H2119.3C22—C23—H23120.7
C4—C3—C2119.4 (4)C23—C24—C25120.1 (4)
C4—C3—H3120.3C23—C24—H24119.9
C2—C3—H3120.3C25—C24—H24119.9
C3—C4—C5120.4 (4)C26—C25—C24120.4 (4)
C3—C4—Br1119.5 (4)C26—C25—H25119.8
C5—C4—Br1120.1 (3)C24—C25—H25119.8
C6—C5—C4120.0 (4)C25—C26—C27120.1 (4)
C6—C5—H5120.0C25—C26—H26119.9
C4—C5—H5120.0C27—C26—H26119.9
C5—C6—C1120.7 (4)C26—C27—C22119.7 (4)
C5—C6—H6119.6C26—C27—H27120.1
C1—C6—H6119.6C22—C27—H27120.1
C8—C7—N1115.3 (4)N7—C28—C29108.9 (3)
C8—C7—C1126.2 (3)N7—C28—C21120.1 (3)
N1—C7—C1118.5 (3)C29—C28—C21131.0 (3)
C7—C8—S1111.1 (3)N9—C29—C28104.0 (3)
C7—C8—H8124.4N9—C29—C30124.2 (3)
S1—C8—H8124.4C28—C29—C30131.5 (3)
N1—C9—N2123.3 (3)C29—C30—H30A109.5
N1—C9—S1116.1 (3)C29—C30—H30B109.5
N2—C9—S1120.5 (3)H30A—C30—H30B109.5
N3—C10—C13121.7 (3)C29—C30—H30C109.5
N3—C10—C11113.7 (3)H30A—C30—H30C109.5
C13—C10—C11124.6 (3)H30B—C30—H30C109.5
C10—C11—C12103.5 (3)C36—C31—C32120.1 (4)
C10—C11—H11A111.1C36—C31—N9120.2 (3)
C12—C11—H11A111.1C32—C31—N9119.6 (3)
C10—C11—H11B111.1C33—C32—C31118.9 (4)
C12—C11—H11B111.1C33—C32—H32120.5
H11A—C11—H11B109.0C31—C32—H32120.5
N2—C12—C19111.6 (3)C32—C33—C34122.5 (4)
N2—C12—C11100.7 (3)C32—C33—H33118.8
C19—C12—C11112.8 (3)C34—C33—H33118.8
N2—C12—H12110.4C33—C34—C35116.9 (4)
C19—C12—H12110.4C33—C34—C37122.0 (4)
C11—C12—H12110.4C35—C34—C37121.1 (4)
C18—C13—C14118.1 (4)C36—C35—C34121.6 (4)
C18—C13—C10120.9 (4)C36—C35—H35119.2
C14—C13—C10120.9 (4)C34—C35—H35119.2
C15—C14—C13120.9 (4)C31—C36—C35120.0 (3)
C15—C14—H14119.6C31—C36—H36120.0
C13—C14—H14119.6C35—C36—H36120.0
C16—C15—C14119.6 (4)C34—C37—H37A109.5
C16—C15—H15120.2C34—C37—H37B109.5
C14—C15—H15120.2H37A—C37—H37B109.5
C17—C16—C15121.1 (4)C34—C37—H37C109.5
C17—C16—Cl1119.4 (3)H37A—C37—H37C109.5
C15—C16—Cl1119.5 (4)H37B—C37—H37C109.5
C16—C17—C18119.2 (4)C9—N1—C7109.6 (3)
C16—C17—H17120.4C9—N2—N3119.4 (3)
C18—C17—H17120.4C9—N2—C12125.8 (3)
C13—C18—C17121.1 (4)N3—N2—C12113.7 (3)
C13—C18—H18119.5C10—N3—N2108.3 (3)
C17—C18—H18119.5C20—N4—N5111.8 (3)
C20—C19—C21104.0 (3)C20—N4—C22127.2 (3)
C20—C19—C12128.0 (3)N5—N4—C22121.0 (3)
C21—C19—C12128.0 (3)C21—N5—N4104.4 (3)
N4—C20—C19108.2 (3)N8—N7—C28109.4 (3)
N4—C20—H20125.9N7—N8—N9107.0 (3)
C19—C20—H20125.9C29—N9—N8110.7 (3)
N5—C21—C19111.7 (3)C29—N9—C31130.0 (3)
N5—C21—C28121.1 (3)N8—N9—C31119.3 (3)
C19—C21—C28127.2 (3)C8—S1—C987.82 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···Br1i0.932.853.726 (4)157
Symmetry code: (i) x1/2, 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.

References

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