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ISSN: 2414-3146

5-[(4-Bromo­phen­yl)diazen­yl]-2-{2-[1-(1H-indol-3-yl)ethyl­­idene]hydrazin­yl}-4-methyl­thia­zole di­methyl­formamide hemisolvate

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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, dNational Center for Petrochemicals Technology, King Abdulaziz City for Science and Technology, PO Box 6086, Riyadh 11442, Saudi Arabia, eDepartment of Chemistry, College of Science, Al-Nahrain University, Baghdad 64021, Iraq, and fSchool of Chemistry, Cardiff University, Main Building, Park Place, Cardiff CF10 3AT, UK
*Correspondence e-mail: gelhiti@ksu.edu.sa

Edited by J. Simpson, University of Otago, New Zealand (Received 26 September 2018; accepted 28 September 2018; online 5 October 2018)

The asymmetric unit of the title compound, 2C20H17BrN6S·C3H7NO, comprises two mol­ecules of the thia­zole derivative and one mol­ecule of di­methyl­formamide (DMF) solvent. The twist angles between the planes through the bromo­phenyl, methyl­thiazolyl and indolyl groups are 10.1 (1) and 44.2 (1)°, respectively, for one mol­ecule and 11.3 (1) and 1.6 (1)° for the other. In the crystal, N—H⋯N hydrogen bonds link four of the main mol­ecules into tetramers. N—H⋯O bonds involving the DMF solvent mol­ecule also occur.

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

Structure description

Heterocycles containing both thia­zole and indole moieties have various biological activities (Gu et al., 1999[Gu, X. H., Wan, X. Z. & Jiang, B. (1999). Bioorg. Med. Chem. Lett. 9, 569-572.]; Guggilapu et al., 2017[Guggilapu, S. D., Guntuku, L., Reddy, T. S., Nagarsenkar, A., Sigalapalli, D. K., Naidu, V. G. M., Bhargava, S. K. & Bathini, N. B. (2017). Eur. J. Med. Chem. 138, 83-95.]; Tantak et al., 2017[Tantak, M. P., Mukherjee, D. D., Kumar, A., Chakrabarti, G. & Kumar, D. (2017). Anticancer Agents Med. Chem. 17, 442-455.]; Vaddula et al., 2016[Vaddula, B. R., Tantak, M. P., Sadana, R., Gonzalez, M. A. & Kumar, D. (2016). Sci. Rep. 6, 23401.]). The crystal structure reported here was obtained as part of a study of this class of compounds.

The asymmetric unit of the title compound comprises two mol­ecules of the thia­zole C20H17BrN6S, and one mol­ecule of di­methyl­formamide (DMF) solvent (Fig. 1[link]). The twist angles between the planes through the bromo­phenyl, methyl­thiazolyl and indolyl groups are 10.1 (1)° and 44.2 (1)° respectively for one mol­ecule (C1–C20) and 11.3 (1)° and 1.6 (1)° for the other (C21–C40). N—H⋯N hydrogen-bonding contacts form rings of four mol­ecules within the crystal (Table 1[link], Fig. 2[link]) with two of the mol­ecules also forming N—H⋯O hydrogen bonds with neighbouring DMF solvent mol­ecules.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯O1 0.86 2.08 2.782 (4) 138
N6—H6A⋯N9i 0.86 2.62 3.292 (4) 136
N6—H6A⋯N10i 0.86 2.42 3.234 (4) 159
N12—H12⋯N3ii 0.86 2.15 3.011 (4) 177
Symmetry codes: (i) -x, -y+2, -z; (ii) x+2, y, z.
[Figure 1]
Figure 1
An ORTEP representation of the asymmetric unit showing 50% probability ellipsoids.
[Figure 2]
Figure 2
A segment of the crystal structure showing hydrogen-bonding contacts as dotted lines.

Synthesis and crystallization

The title compound was synthesized by the reaction of 2-[1-(1H-indol-3-yl)ethyl­idene]hydrazinecarbo­thio­amide and N′-(4-bromo­phen­yl)-2-oxo­propane­hydrazonoyl chloride in refluxing ethanol (4 h) containing tri­ethyl­amine as a base. Crystallization of the crude product using di­methyl­formamide as solvent gave colourless crystals (65%), m.p. 260°C (lit m.p. 260–261°C; Abdel-Gawad et al., 2010[Abdel-Gawad, H., Mohamed, H. A., Dawood, K. M. & Badria, F. A. (2010). Chem. Pharm. Bull. 58, 1529-1531.]).

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula 2C20H17BrN6S·C3H7NO
Mr 979.83
Crystal system, space group Triclinic, P[\overline{1}]
Temperature (K) 293
a, b, c (Å) 9.9957 (6), 14.5325 (9), 15.8353 (10)
α, β, γ (°) 81.671 (5), 81.344 (5), 80.469 (5)
V3) 2225.7 (2)
Z 2
Radiation type Mo Kα
μ (mm−1) 1.97
Crystal size (mm) 0.25 × 0.09 × 0.04
 
Data collection
Diffractometer Rigaku Oxford Diffraction SuperNova, Dual, Cu at zero, Atlas
Absorption correction Gaussian (CrysAlis PRO; Rigaku OD, 2015[Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.])
Tmin, Tmax 0.827, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections 19885, 10602, 5116
Rint 0.036
(sin θ/λ)max−1) 0.701
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.145, 1.01
No. of reflections 10602
No. of parameters 556
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.49, −0.57
Computer programs: CrysAlis PRO (Rigaku OD, 2015[Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]), SHELXS (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL2018 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]), 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 (Rigaku OD, 2015); cell refinement: 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: ORTEP-3 for Windows and WinGX (Farrugia, 2012) and CHEMDRAW Ultra (Cambridge Soft, 2001).

5-[(4-Bromophenyl)diazenyl]-2-{2-[1-(1H-indol-3-yl)ethylidene]hydrazinyl}-4-methylthiazole dimethylformamide hemisolvate top
Crystal data top
2C20H17BrN6S·C3H7NOZ = 2
Mr = 979.83F(000) = 1000
Triclinic, P1Dx = 1.462 Mg m3
a = 9.9957 (6) ÅMo Kα radiation, λ = 0.71073 Å
b = 14.5325 (9) ÅCell parameters from 3549 reflections
c = 15.8353 (10) Åθ = 3.3–24.0°
α = 81.671 (5)°µ = 1.97 mm1
β = 81.344 (5)°T = 293 K
γ = 80.469 (5)°Needle, colourless
V = 2225.7 (2) Å30.25 × 0.09 × 0.04 mm
Data collection top
Rigaku Oxford Diffraction SuperNova, Dual, Cu at zero, Atlas
diffractometer
5116 reflections with I > 2σ(I)
ω scansRint = 0.036
Absorption correction: gaussian
(CrysAlis PRO; Rigaku OD, 2015)
θmax = 29.9°, θmin = 1.3°
Tmin = 0.827, Tmax = 1.000h = 1212
19885 measured reflectionsk = 1817
10602 independent reflectionsl = 2019
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.056H-atom parameters constrained
wR(F2) = 0.145 w = 1/[σ2(Fo2) + (0.0515P)2 + 0.5647P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
10602 reflectionsΔρmax = 0.49 e Å3
556 parametersΔρmin = 0.57 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.3683 (4)0.4890 (3)0.2966 (3)0.0661 (11)
C20.3605 (4)0.5387 (3)0.2167 (3)0.0725 (12)
H20.4390150.5428220.1773840.087*
C30.2340 (4)0.5828 (3)0.1951 (3)0.0690 (12)
H30.2276960.6167940.1410650.083*
C40.1170 (3)0.5764 (3)0.2536 (2)0.0553 (10)
C50.1270 (4)0.5278 (3)0.3346 (2)0.0686 (12)
H50.0493020.5240210.3747180.082*
C60.2539 (4)0.4849 (3)0.3554 (3)0.0755 (13)
H60.2615080.4527950.4100690.091*
C70.2388 (3)0.6543 (3)0.2642 (2)0.0503 (9)
C80.3603 (3)0.6609 (3)0.3284 (2)0.0500 (9)
C90.3516 (4)0.6225 (3)0.4198 (2)0.0662 (11)
H9A0.2963760.6574670.4439280.099*
H9B0.3109210.5576190.4231430.099*
H9C0.4417420.6275090.4514110.099*
C100.4547 (3)0.7334 (3)0.2135 (2)0.0503 (9)
C110.7037 (4)0.9302 (3)0.0909 (3)0.0775 (13)
H11A0.7874200.9112400.0817280.116*
H11B0.7022070.9948220.0676570.116*
H11C0.6977370.9229450.1515320.116*
C120.5837 (3)0.8696 (3)0.0466 (2)0.0532 (9)
C130.5446 (3)0.8901 (3)0.0446 (2)0.0527 (9)
C140.5892 (4)0.9712 (3)0.0958 (2)0.0653 (11)
H140.6497071.0217790.0762430.078*
C150.4560 (3)0.8309 (3)0.1020 (2)0.0529 (9)
C160.4509 (4)0.8814 (3)0.1848 (2)0.0582 (10)
C170.3895 (4)0.7384 (3)0.0925 (3)0.0678 (11)
H170.3893590.7038290.0382360.081*
C180.3240 (4)0.6987 (3)0.1647 (3)0.0839 (14)
H180.2815170.6365630.1591920.101*
C190.3210 (4)0.7514 (4)0.2458 (3)0.0817 (14)
H190.2755330.7232250.2933360.098*
C200.3824 (4)0.8428 (4)0.2583 (3)0.0717 (12)
H200.3788760.8774000.3126120.086*
C210.0369 (4)0.8433 (3)0.8874 (2)0.0685 (12)
C220.1724 (4)0.8075 (3)0.8889 (3)0.0677 (11)
H220.2054560.7854960.9411020.081*
C230.2595 (4)0.8043 (3)0.8127 (2)0.0627 (11)
H230.3511160.7789490.8132630.075*
C240.2104 (4)0.8386 (3)0.7357 (2)0.0562 (10)
C250.0725 (4)0.8708 (3)0.7344 (3)0.0693 (12)
H250.0384630.8912440.6823300.083*
C260.0152 (4)0.8725 (3)0.8116 (3)0.0752 (13)
H260.1082720.8933790.8114420.090*
C270.3534 (3)0.8933 (3)0.5193 (2)0.0514 (9)
C280.3153 (3)0.9414 (3)0.4369 (2)0.0540 (9)
C290.1725 (4)0.9861 (3)0.4279 (3)0.0703 (12)
H29A0.1471101.0358980.4635500.105*
H29B0.1119920.9399950.4453460.105*
H29C0.1661131.0113120.3688910.105*
C300.5383 (3)0.9026 (3)0.3979 (2)0.0514 (9)
C310.8812 (4)0.8946 (3)0.2322 (2)0.0685 (12)
H31A0.8434920.8555890.2007460.103*
H31B0.9745390.8985120.2082180.103*
H31C0.8290830.9564670.2283390.103*
C320.8760 (4)0.8529 (3)0.3249 (2)0.0523 (9)
C331.0005 (3)0.8060 (3)0.3569 (2)0.0526 (9)
C341.1291 (4)0.7972 (3)0.3090 (2)0.0624 (11)
H341.1471380.8211490.2513460.075*
C351.0228 (3)0.7596 (3)0.4419 (2)0.0507 (9)
C361.1629 (3)0.7248 (3)0.4387 (2)0.0571 (10)
C370.9387 (4)0.7430 (3)0.5204 (2)0.0646 (11)
H370.8454200.7652640.5255770.077*
C380.9978 (4)0.6929 (3)0.5895 (3)0.0821 (15)
H380.9430530.6812690.6417370.099*
C391.1368 (4)0.6592 (4)0.5834 (3)0.0864 (15)
H391.1729340.6257970.6315150.104*
C401.2216 (4)0.6739 (3)0.5084 (3)0.0726 (12)
H401.3146430.6509800.5041840.087*
C410.0191 (5)0.6113 (3)0.0223 (3)0.0853 (14)
H410.0680230.6362380.0358120.102*
C420.0817 (7)0.5992 (4)0.1745 (3)0.119 (2)
H42A0.0122510.6267210.1758020.178*
H42B0.0965830.5390150.1953530.178*
H42C0.1397720.6396130.2103230.178*
C430.2499 (6)0.5465 (4)0.0693 (4)0.127 (2)
H43A0.3115720.5912280.0902210.191*
H43B0.2785690.4912020.0978070.191*
H43C0.2503810.5298120.0083730.191*
N10.0093 (3)0.6186 (2)0.22832 (19)0.0587 (8)
H10.0152440.6431120.1759840.070*
N20.1210 (3)0.6202 (2)0.28697 (18)0.0538 (8)
N30.4736 (3)0.7028 (2)0.30121 (17)0.0531 (8)
N40.5533 (3)0.7801 (2)0.17471 (18)0.0578 (8)
N50.5105 (3)0.7997 (2)0.08630 (18)0.0556 (8)
N60.5323 (3)0.9668 (2)0.1789 (2)0.0667 (9)
H6A0.5451841.0103790.2209750.080*
N70.3037 (3)0.8407 (2)0.66017 (18)0.0615 (9)
H70.3865010.8130220.6613120.074*
N80.2636 (3)0.8859 (2)0.58613 (19)0.0547 (8)
N90.4131 (3)0.9447 (2)0.37360 (18)0.0552 (8)
N100.6473 (3)0.9013 (2)0.34273 (18)0.0553 (8)
N110.7640 (3)0.8559 (2)0.37912 (17)0.0543 (8)
N121.2240 (3)0.7495 (2)0.3570 (2)0.0676 (9)
H121.3098080.7365570.3391690.081*
N130.1136 (4)0.5873 (3)0.0864 (2)0.0866 (12)
O10.0371 (4)0.6034 (3)0.0529 (2)0.1044 (12)
S10.28472 (9)0.70423 (7)0.16186 (5)0.0551 (3)
S20.53169 (9)0.85338 (7)0.50777 (6)0.0563 (3)
Br10.53923 (5)0.42261 (4)0.32500 (4)0.0973 (2)
Br20.07975 (6)0.84842 (4)0.99418 (3)0.1142 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.044 (2)0.079 (3)0.075 (3)0.004 (2)0.0138 (19)0.018 (2)
C20.046 (2)0.094 (3)0.073 (3)0.002 (2)0.0002 (19)0.013 (2)
C30.048 (2)0.089 (3)0.061 (2)0.000 (2)0.0017 (18)0.003 (2)
C40.043 (2)0.066 (3)0.054 (2)0.0027 (18)0.0023 (16)0.0114 (18)
C50.049 (2)0.098 (3)0.053 (2)0.001 (2)0.0032 (17)0.005 (2)
C60.062 (3)0.095 (3)0.065 (3)0.002 (2)0.016 (2)0.002 (2)
C70.045 (2)0.057 (2)0.045 (2)0.0013 (17)0.0023 (15)0.0073 (16)
C80.046 (2)0.055 (2)0.042 (2)0.0010 (17)0.0028 (15)0.0020 (16)
C90.062 (2)0.085 (3)0.042 (2)0.007 (2)0.0015 (17)0.0022 (19)
C100.0437 (19)0.058 (2)0.044 (2)0.0044 (17)0.0026 (15)0.0010 (16)
C110.063 (3)0.092 (3)0.060 (3)0.015 (2)0.0027 (19)0.006 (2)
C120.046 (2)0.063 (3)0.048 (2)0.0009 (18)0.0086 (16)0.0009 (18)
C130.050 (2)0.062 (3)0.042 (2)0.0020 (18)0.0095 (15)0.0040 (17)
C140.071 (3)0.070 (3)0.049 (2)0.002 (2)0.0030 (19)0.0037 (19)
C150.0446 (19)0.064 (3)0.048 (2)0.0047 (18)0.0088 (15)0.0014 (18)
C160.051 (2)0.076 (3)0.048 (2)0.010 (2)0.0048 (17)0.0084 (19)
C170.062 (2)0.074 (3)0.064 (3)0.000 (2)0.006 (2)0.009 (2)
C180.075 (3)0.084 (3)0.087 (4)0.008 (3)0.002 (2)0.023 (3)
C190.064 (3)0.111 (4)0.069 (3)0.010 (3)0.010 (2)0.033 (3)
C200.061 (2)0.102 (4)0.053 (3)0.019 (3)0.0021 (19)0.012 (2)
C210.075 (3)0.067 (3)0.052 (2)0.004 (2)0.014 (2)0.003 (2)
C220.073 (3)0.078 (3)0.052 (2)0.018 (2)0.006 (2)0.004 (2)
C230.048 (2)0.085 (3)0.054 (2)0.017 (2)0.0049 (17)0.000 (2)
C240.050 (2)0.067 (3)0.048 (2)0.0084 (19)0.0041 (16)0.0063 (18)
C250.055 (2)0.084 (3)0.058 (2)0.007 (2)0.0014 (18)0.001 (2)
C260.055 (2)0.088 (3)0.066 (3)0.008 (2)0.010 (2)0.002 (2)
C270.0433 (19)0.059 (2)0.049 (2)0.0037 (17)0.0014 (15)0.0069 (17)
C280.045 (2)0.062 (3)0.054 (2)0.0048 (18)0.0076 (17)0.0051 (18)
C290.047 (2)0.085 (3)0.072 (3)0.000 (2)0.0087 (19)0.003 (2)
C300.047 (2)0.061 (2)0.042 (2)0.0024 (18)0.0027 (15)0.0036 (17)
C310.059 (2)0.091 (3)0.050 (2)0.012 (2)0.0064 (17)0.002 (2)
C320.050 (2)0.056 (2)0.048 (2)0.0083 (17)0.0035 (16)0.0056 (17)
C330.0415 (19)0.063 (3)0.051 (2)0.0071 (17)0.0041 (15)0.0095 (18)
C340.050 (2)0.077 (3)0.054 (2)0.007 (2)0.0087 (18)0.007 (2)
C350.0411 (19)0.062 (2)0.048 (2)0.0073 (17)0.0018 (15)0.0093 (17)
C360.042 (2)0.070 (3)0.056 (2)0.0045 (18)0.0043 (17)0.0122 (19)
C370.044 (2)0.088 (3)0.055 (2)0.002 (2)0.0014 (17)0.005 (2)
C380.054 (2)0.127 (4)0.053 (3)0.002 (3)0.0039 (19)0.002 (2)
C390.057 (3)0.122 (4)0.070 (3)0.008 (3)0.013 (2)0.004 (3)
C400.046 (2)0.094 (3)0.072 (3)0.007 (2)0.007 (2)0.012 (2)
C410.099 (4)0.082 (3)0.069 (3)0.011 (3)0.001 (3)0.005 (3)
C420.177 (6)0.129 (5)0.061 (3)0.060 (4)0.002 (3)0.019 (3)
C430.117 (5)0.124 (5)0.121 (5)0.018 (4)0.016 (4)0.023 (4)
N10.0427 (17)0.076 (2)0.0501 (18)0.0044 (15)0.0012 (13)0.0040 (15)
N20.0424 (17)0.063 (2)0.0523 (18)0.0013 (15)0.0014 (13)0.0090 (14)
N30.0461 (17)0.064 (2)0.0405 (17)0.0002 (15)0.0037 (12)0.0017 (14)
N40.0459 (17)0.072 (2)0.0462 (18)0.0031 (16)0.0017 (13)0.0045 (15)
N50.0464 (16)0.069 (2)0.0433 (17)0.0012 (15)0.0023 (13)0.0034 (14)
N60.078 (2)0.067 (2)0.048 (2)0.0081 (19)0.0084 (16)0.0102 (15)
N70.0465 (17)0.082 (2)0.0475 (19)0.0003 (16)0.0031 (13)0.0008 (16)
N80.0475 (17)0.064 (2)0.0500 (19)0.0058 (15)0.0004 (14)0.0064 (15)
N90.0444 (17)0.070 (2)0.0475 (18)0.0042 (15)0.0061 (13)0.0009 (15)
N100.0461 (17)0.071 (2)0.0439 (17)0.0053 (15)0.0013 (13)0.0015 (14)
N110.0433 (16)0.072 (2)0.0419 (16)0.0020 (15)0.0003 (13)0.0008 (14)
N120.0408 (17)0.088 (3)0.065 (2)0.0022 (17)0.0134 (15)0.0103 (18)
N130.105 (3)0.092 (3)0.060 (2)0.019 (2)0.004 (2)0.011 (2)
O10.112 (3)0.133 (3)0.055 (2)0.007 (2)0.0013 (17)0.0048 (19)
S10.0430 (5)0.0724 (7)0.0417 (5)0.0009 (4)0.0030 (4)0.0005 (4)
S20.0450 (5)0.0737 (7)0.0425 (5)0.0020 (5)0.0005 (4)0.0007 (4)
Br10.0541 (3)0.1219 (5)0.1132 (4)0.0158 (3)0.0292 (3)0.0197 (3)
Br20.1249 (5)0.1113 (5)0.0695 (3)0.0243 (4)0.0413 (3)0.0070 (3)
Geometric parameters (Å, º) top
C1—C61.365 (6)C25—H250.9300
C1—C21.369 (6)C26—H260.9300
C1—Br11.901 (3)C27—N81.284 (4)
C2—C31.387 (5)C27—C281.461 (5)
C2—H20.9300C27—S21.771 (3)
C3—C41.384 (5)C28—N91.292 (4)
C3—H30.9300C28—C291.485 (5)
C4—C51.382 (5)C29—H29A0.9600
C4—N11.398 (4)C29—H29B0.9600
C5—C61.382 (5)C29—H29C0.9600
C5—H50.9300C30—N101.290 (4)
C6—H60.9300C30—N91.382 (4)
C7—N21.283 (4)C30—S21.778 (3)
C7—C81.461 (4)C31—C321.501 (5)
C7—S11.771 (3)C31—H31A0.9600
C8—N31.297 (4)C31—H31B0.9600
C8—C91.484 (5)C31—H31C0.9600
C9—H9A0.9600C32—N111.303 (4)
C9—H9B0.9600C32—C331.443 (5)
C9—H9C0.9600C33—C341.387 (5)
C10—N41.284 (4)C33—C351.447 (5)
C10—N31.390 (4)C34—N121.344 (5)
C10—S11.783 (3)C34—H340.9300
C11—C121.510 (5)C35—C361.404 (5)
C11—H11A0.9600C35—C371.406 (5)
C11—H11B0.9600C36—N121.370 (5)
C11—H11C0.9600C36—C401.388 (5)
C12—N51.292 (4)C37—C381.378 (5)
C12—C131.441 (5)C37—H370.9300
C13—C141.379 (5)C38—C391.389 (5)
C13—C151.442 (5)C38—H380.9300
C14—N61.358 (5)C39—C401.363 (6)
C14—H140.9300C39—H390.9300
C15—C171.396 (5)C40—H400.9300
C15—C161.405 (5)C41—O11.217 (5)
C16—N61.373 (5)C41—N131.321 (6)
C16—C201.400 (5)C41—H410.9300
C17—C181.382 (6)C42—N131.458 (6)
C17—H170.9300C42—H42A0.9600
C18—C191.397 (6)C42—H42B0.9600
C18—H180.9300C42—H42C0.9600
C19—C201.367 (6)C43—N131.442 (6)
C19—H190.9300C43—H43A0.9600
C20—H200.9300C43—H43B0.9600
C21—C261.363 (6)C43—H43C0.9600
C21—C221.370 (6)N1—N21.340 (4)
C21—Br21.908 (4)N1—H10.8600
C22—C231.380 (5)N4—N51.403 (4)
C22—H220.9300N6—H6A0.8600
C23—C241.378 (5)N7—N81.341 (4)
C23—H230.9300N7—H70.8600
C24—C251.382 (5)N10—N111.401 (4)
C24—N71.401 (4)N12—H120.8600
C25—C261.394 (5)
C6—C1—C2120.7 (3)C28—C27—S2109.2 (2)
C6—C1—Br1119.6 (3)N9—C28—C27116.2 (3)
C2—C1—Br1119.7 (3)N9—C28—C29122.4 (3)
C1—C2—C3119.1 (4)C27—C28—C29121.3 (3)
C1—C2—H2120.4C28—C29—H29A109.5
C3—C2—H2120.4C28—C29—H29B109.5
C4—C3—C2120.4 (4)H29A—C29—H29B109.5
C4—C3—H3119.8C28—C29—H29C109.5
C2—C3—H3119.8H29A—C29—H29C109.5
C5—C4—C3119.7 (3)H29B—C29—H29C109.5
C5—C4—N1121.5 (3)N10—C30—N9120.3 (3)
C3—C4—N1118.8 (3)N10—C30—S2125.4 (3)
C4—C5—C6119.1 (4)N9—C30—S2114.4 (2)
C4—C5—H5120.4C32—C31—H31A109.5
C6—C5—H5120.4C32—C31—H31B109.5
C1—C6—C5120.8 (4)H31A—C31—H31B109.5
C1—C6—H6119.6C32—C31—H31C109.5
C5—C6—H6119.6H31A—C31—H31C109.5
N2—C7—C8120.3 (3)H31B—C31—H31C109.5
N2—C7—S1130.1 (3)N11—C32—C33117.2 (3)
C8—C7—S1109.5 (2)N11—C32—C31123.7 (3)
N3—C8—C7116.5 (3)C33—C32—C31119.1 (3)
N3—C8—C9122.6 (3)C34—C33—C32125.2 (3)
C7—C8—C9120.8 (3)C34—C33—C35104.9 (3)
C8—C9—H9A109.5C32—C33—C35130.0 (3)
C8—C9—H9B109.5N12—C34—C33110.9 (3)
H9A—C9—H9B109.5N12—C34—H34124.6
C8—C9—H9C109.5C33—C34—H34124.6
H9A—C9—H9C109.5C36—C35—C37117.9 (3)
H9B—C9—H9C109.5C36—C35—C33107.1 (3)
N4—C10—N3121.4 (3)C37—C35—C33135.0 (3)
N4—C10—S1123.9 (3)N12—C36—C40128.8 (3)
N3—C10—S1114.7 (2)N12—C36—C35107.7 (3)
C12—C11—H11A109.5C40—C36—C35123.4 (3)
C12—C11—H11B109.5C38—C37—C35118.4 (3)
H11A—C11—H11B109.5C38—C37—H37120.8
C12—C11—H11C109.5C35—C37—H37120.8
H11A—C11—H11C109.5C37—C38—C39121.8 (4)
H11B—C11—H11C109.5C37—C38—H38119.1
N5—C12—C13116.7 (3)C39—C38—H38119.1
N5—C12—C11123.7 (3)C40—C39—C38121.6 (4)
C13—C12—C11119.6 (3)C40—C39—H39119.2
C14—C13—C12126.1 (3)C38—C39—H39119.2
C14—C13—C15105.7 (3)C39—C40—C36116.9 (3)
C12—C13—C15128.2 (3)C39—C40—H40121.5
N6—C14—C13110.4 (3)C36—C40—H40121.5
N6—C14—H14124.8O1—C41—N13125.2 (5)
C13—C14—H14124.8O1—C41—H41117.4
C17—C15—C16118.6 (3)N13—C41—H41117.4
C17—C15—C13134.2 (3)N13—C42—H42A109.5
C16—C15—C13106.9 (3)N13—C42—H42B109.5
N6—C16—C20129.0 (4)H42A—C42—H42B109.5
N6—C16—C15107.9 (3)N13—C42—H42C109.5
C20—C16—C15122.9 (4)H42A—C42—H42C109.5
C18—C17—C15119.2 (4)H42B—C42—H42C109.5
C18—C17—H17120.4N13—C43—H43A109.5
C15—C17—H17120.4N13—C43—H43B109.5
C17—C18—C19120.4 (4)H43A—C43—H43B109.5
C17—C18—H18119.8N13—C43—H43C109.5
C19—C18—H18119.8H43A—C43—H43C109.5
C20—C19—C18122.6 (4)H43B—C43—H43C109.5
C20—C19—H19118.7N2—N1—C4118.9 (3)
C18—C19—H19118.7N2—N1—H1120.5
C19—C20—C16116.3 (4)C4—N1—H1120.5
C19—C20—H20121.8C7—N2—N1119.9 (3)
C16—C20—H20121.8C8—N3—C10111.6 (3)
C26—C21—C22121.3 (4)C10—N4—N5110.8 (3)
C26—C21—Br2120.2 (3)C12—N5—N4115.3 (3)
C22—C21—Br2118.4 (3)C14—N6—C16109.1 (3)
C21—C22—C23119.6 (4)C14—N6—H6A125.5
C21—C22—H22120.2C16—N6—H6A125.5
C23—C22—H22120.2N8—N7—C24119.9 (3)
C24—C23—C22119.9 (4)N8—N7—H7120.1
C24—C23—H23120.1C24—N7—H7120.1
C22—C23—H23120.1C27—N8—N7118.7 (3)
C23—C24—C25120.0 (3)C28—N9—C30112.3 (3)
C23—C24—N7118.3 (3)C30—N10—N11112.1 (3)
C25—C24—N7121.7 (3)C32—N11—N10113.7 (3)
C24—C25—C26119.7 (4)C34—N12—C36109.4 (3)
C24—C25—H25120.2C34—N12—H12125.3
C26—C25—H25120.2C36—N12—H12125.3
C21—C26—C25119.3 (4)C41—N13—C43120.0 (4)
C21—C26—H26120.4C41—N13—C42121.1 (5)
C25—C26—H26120.4C43—N13—C42118.9 (4)
N8—C27—C28121.0 (3)C7—S1—C1087.65 (16)
N8—C27—S2129.7 (3)C27—S2—C3087.89 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.862.082.782 (4)138
N6—H6A···N9i0.862.623.292 (4)136
N6—H6A···N10i0.862.423.234 (4)159
N12—H12···N3ii0.862.153.011 (4)177
Symmetry codes: (i) x, y+2, z; (ii) x+2, y, z.
 

Footnotes

Additional corresponding 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).

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