2-({6-[5-Methyl-1-(4-methylphenyl)-1H-1,2,3-triazol-4-yl]imidazo[2,1-b]thia­zol-5-yl}methyl­idene)hydrazinecarbo­thio­amide di­methyl­formamide 0.25-solvate

El-Hiti, G.A.; Abdel-Wahab, B.F.; Alotaibi, M.H.; Hegazy, A.S.; Kariuki, B.M.

doi:10.1107/S2414314618000871

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 3| Part 1| January 2018| x180087

https://doi.org/10.1107/S2414314618000871

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2-({6-[5-Methyl-1-(4-methylphenyl)-1H-1,2,3-triazol-4-yl]imidazo[2,1-b]thiazol-5-yl}methylidene)hydrazinecarbothioamide dimethylformamide 0.25-solvate

Gamal A. El-Hiti,^a ^* Bakr F. Abdel-Wahab,^b,^c Mohammad Hayal Alotaibi,^d Amany S. Hegazy ^e and Benson M. Kariuki ^e ‡

^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, UK
^*Correspondence e-mail: gelhiti@ksu.edu.sa

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 6 January 2018; accepted 14 January 2018; online 19 January 2018)

The asymmetric unit of the title solvate, C₁₇H₁₆N₈S₂·0.25C₃H₇NO, consists of two C₁₇H₁₆N₈S₂ molecules and a dimethylformamide molecule disordered about a crystallographic inversion centre. Both triazole molecules feature an intramolecular C—H⋯N interaction, which generates an S(6) ring in each case. In the crystal, the components are linked by N—H⋯N and N—H⋯S hydrogen bonds to form [001] chains, which are cross-linked by weak C—H⋯O, C—H⋯N and C—H⋯S interactions.

Keywords: crystal structure; heterocycle; triazole.

CCDC reference: 1816864

Structure description

Heterocyclic compounds that contain the thiosemicarbazone residue show a number of biological applications (see, for example, Salman et al., 2016 ; Yusuf & Jain, 2014 ; Abdel-Wahab et al., 2017 ). As part of our studies in this area, we now describe the synthesis and structure of the title solvate.

The asymmetric unit consists of two independent C₁₇H₁₆N₈S₂ molecules (A and B) and half a molecule of dimethyl formamide solvent disordered about an inversion centre (Fig. 1). In molecule A, the dihedral angles between the triazole ring and the toluyl and imidazole rings are 81.1 (2) and 8.5 (2)°, respectively. Equivalent values for molecule B are 58.8 (2) and 13.83 (19)°, respectively. Both molecules feature an intramolecular C—H⋯N interaction, which generates an S(6) ring in each case.

Figure 1
The molecular structure of the title solvate showing 50% displacement ellipsoids.

In the crystal, N—H⋯S and N—H⋯N hydrogen bonds (Table 1) with N⋯X distances in the range 3.024 (4)–3.502 (3) Å lead to the formation of [001] chains (Fig. 2), which are cross-linked by weak C—H⋯N, C—H⋯O and C—H⋯S interactions.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10A⋯N5	0.96	2.39	3.074 (4)	128
C27—H27A⋯N13	0.96	2.41	3.082 (4)	127
N1—H1A⋯N7ⁱ	0.86	2.62	3.200 (4)	126
N1—H1B⋯S3ⁱⁱ	0.86	2.62	3.470 (3)	172
N2—H2A⋯S3ⁱⁱⁱ	0.86	2.65	3.502 (3)	174
N9—H9A⋯N15ⁱ	0.86	2.34	3.024 (4)	136
N9—H9B⋯S1^iv	0.86	2.64	3.433 (3)	154
N10—H10⋯S1^v	0.86	2.55	3.388 (3)	166
C5—H5⋯O1^vi	0.93	2.59	3.472 (10)	158
C36—H36C⋯S3^vii	0.96	2.72	3.536 (14)	143
C37—H37B⋯N6^viii	0.96	2.45	3.111 (11)	126
C37—H37C⋯S3^ix	0.96	2.75	3.706 (13)	175
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) x-1, y, z-1; (iii) $[x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iv) $[x+1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (v) x+1, y, z+1; (vi) x, y, z-1; (vii) x-1, y, z; (viii) $[-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ix) -x+1, -y, -z+2.

Figure 2
A view of a segment of the crystal structure viewed down the b axis. Intermolecular contacts are shown as blue dotted lines.

Synthesis and crystallization

The title compound, which crystallized as a 0.25 dimethylformamide solvate, was synthesized from a mixture of 6-[5-methyl-1-(4-tolyl)-1H-1,2,3-triazol-4-yl]imidazo[2,1-b]thiazole-5-carbaldehyde and thiosemicarbazide in boiling dry ethanol for 4 h under catalytic acidic conditions (glacial acetic acid). The reaction mixture was left to cool to room temperature and the solid produced was collected, washed with ethanol and recrystallized as yellow plates from dimethylformamide solution, m.p. 229–230°C (Abdel-Wahab et al., 2017).

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	4C₁₇H₁₆N₈S₂·C₃H₇NO
M_r	1659.08
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	18.3427 (14), 13.5855 (10), 16.9385 (12)
β (°)	110.393 (9)
V (Å³)	3956.4 (5)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.29
Crystal size (mm)	0.38 × 0.21 × 0.19

Data collection
Diffractometer	Agilent SuperNova, Dual, Cu at zero, Atlas
Absorption correction	Gaussian (CrysAlis PRO; Agilent, 2014 )
T_min, T_max	0.996, 0.998
No. of measured, independent and observed [I > 2σ(I)] reflections	22546, 9646, 5318
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.702

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.181, 1.04
No. of reflections	9646
No. of parameters	533
No. of restraints	61
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.29
Computer programs: CrysAlis PRO (Agilent, 2014), SHELXS2013 (Sheldrick, 2008 ), SHELXL2013 (Sheldrick, 2015 ), ORTEP-3 for Windows and WinGX (Farrugia, 2012 ) and CHEMDRAW Ultra (Cambridge Soft, 2001 ).

Structural data

CCDC reference: 1816864

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314618000871/hb4203sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314618000871/hb4203Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314618000871/hb4203Isup3.cml

checkCIF report

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: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (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).

2-({6-[5-Methyl-1-(4-methylphenyl)-1H-1,2,3-triazol-4-yl]imidazo[2,1-b]thiazol-5-yl}methylidene)hydrazinecarbothioamide dimethylformamide 0.25-solvate top

Crystal data top

4C₁₇H₁₆N₈S₂·C₃H₇NO	F(000) = 1728
M_r = 1659.08	D_x = 1.393 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 18.3427 (14) Å	Cell parameters from 4302 reflections
b = 13.5855 (10) Å	θ = 3.8–25.9°
c = 16.9385 (12) Å	µ = 0.29 mm⁻¹
β = 110.393 (9)°	T = 296 K
V = 3956.4 (5) Å³	Plate, yellow
Z = 2	0.38 × 0.21 × 0.19 mm

Data collection top

Agilent SuperNova, Dual, Cu at zero, Atlas diffractometer	5318 reflections with I > 2σ(I)
ω scans	R_int = 0.049
Absorption correction: gaussian (CrysAlisPro; Agilent, 2014)	θ_max = 30.0°, θ_min = 2.4°
T_min = 0.996, T_max = 0.998	h = −24→23
22546 measured reflections	k = −18→14
9646 independent reflections	l = −23→22

Refinement top

Refinement on F²	61 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.064	H-atom parameters constrained
wR(F²) = 0.181	w = 1/[σ²(F_o²) + (0.060P)² + 2.4742P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
9646 reflections	Δρ_max = 0.45 e Å⁻³
533 parameters	Δρ_min = −0.29 e Å⁻³

Special details top

Experimental. Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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. Methyl C—H bonds were fixed at 0.96 Å, with displacement parameters 1.5 times U_eq(C), and were allowed to spin about the C—C/C—N bonds. N—H bonds were fixed at 0.86 Å and sp² C—H distances were set to 0.93 Å and their U(iso) set to 1.2 times the U_eq for the atoms to which they are bonded. The DMF solvent molecule is diordered about a crystallographic inversion centre.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	−0.17220 (19)	0.2265 (2)	0.22798 (18)	0.0442 (7)
C2	−0.03664 (18)	0.1621 (2)	0.42338 (19)	0.0448 (7)
H2	−0.0605	0.1912	0.4578	0.054*
C3	0.03317 (17)	0.1064 (2)	0.45952 (18)	0.0416 (7)
C4	0.0536 (2)	0.0284 (3)	0.3275 (2)	0.0526 (9)
H4	0.0134	0.0543	0.2821	0.063*
C5	0.1076 (2)	−0.0338 (3)	0.3208 (2)	0.0578 (9)
H5	0.1087	−0.0562	0.2693	0.069*
C6	0.12846 (19)	0.0026 (2)	0.46744 (19)	0.0452 (7)
C7	0.08037 (17)	0.0885 (2)	0.54231 (18)	0.0425 (7)
C8	0.07685 (17)	0.1309 (3)	0.61939 (19)	0.0465 (8)
C9	0.12373 (18)	0.1110 (3)	0.70155 (19)	0.0481 (8)
C10	0.1875 (2)	0.0397 (3)	0.7394 (2)	0.0657 (10)
H10A	0.1948	0.0001	0.6958	0.099*
H10B	0.1744	−0.0020	0.7783	0.099*
H10C	0.2347	0.0747	0.7687	0.099*
C11	0.1323 (2)	0.1929 (3)	0.8362 (2)	0.0583 (10)
C12	0.1221 (3)	0.1250 (5)	0.8906 (3)	0.118 (2)
H12	0.0917	0.0695	0.8706	0.142*
C13	0.1585 (3)	0.1405 (5)	0.9772 (3)	0.113 (2)
H13	0.1510	0.0947	1.0144	0.136*
C14	0.2041 (2)	0.2197 (3)	1.0089 (2)	0.0658 (11)
C15	0.2145 (3)	0.2844 (3)	0.9527 (2)	0.0710 (11)
H15	0.2467	0.3385	0.9727	0.085*
C16	0.1788 (2)	0.2725 (3)	0.8668 (2)	0.0651 (10)
H16	0.1864	0.3187	0.8299	0.078*
C17	0.2440 (3)	0.2316 (4)	1.1029 (2)	0.0878 (15)
H17A	0.2992	0.2261	1.1168	0.132*
H17B	0.2263	0.1812	1.1316	0.132*
H17C	0.2317	0.2951	1.1198	0.132*
C18	0.69548 (19)	0.2204 (3)	0.92434 (19)	0.0472 (8)
C19	0.55451 (17)	0.3166 (2)	0.99815 (18)	0.0427 (7)
H19	0.5798	0.3042	1.0552	0.051*
C20	0.48128 (17)	0.3667 (2)	0.97028 (17)	0.0403 (7)
C21	0.4551 (2)	0.3982 (3)	0.81034 (18)	0.0494 (8)
H21	0.4974	0.3692	0.8012	0.059*
C22	0.3979 (2)	0.4438 (3)	0.7517 (2)	0.0603 (10)
H22	0.3956	0.4497	0.6962	0.072*
C23	0.37887 (19)	0.4471 (3)	0.88651 (18)	0.0457 (8)
C24	0.43284 (17)	0.3984 (2)	1.01217 (17)	0.0406 (7)
C25	0.44181 (17)	0.3852 (3)	1.10053 (18)	0.0430 (7)
C26	0.40246 (17)	0.4329 (2)	1.14538 (17)	0.0409 (7)
C27	0.3392 (2)	0.5065 (3)	1.1218 (2)	0.0523 (9)
H27A	0.3301	0.5290	1.0655	0.078*
H27B	0.3538	0.5612	1.1600	0.078*
H27C	0.2926	0.4770	1.1247	0.078*
C28	0.41642 (19)	0.4155 (3)	1.29788 (18)	0.0481 (8)
C29	0.4243 (3)	0.5090 (3)	1.3295 (2)	0.0717 (12)
H29	0.4406	0.5597	1.3026	0.086*
C30	0.4079 (3)	0.5276 (4)	1.4015 (3)	0.0833 (14)
H30	0.4132	0.5914	1.4227	0.100*
C31	0.3838 (2)	0.4544 (3)	1.4426 (2)	0.0651 (11)
C32	0.3755 (2)	0.3616 (3)	1.4096 (2)	0.0644 (11)
H32	0.3596	0.3110	1.4368	0.077*
C33	0.3905 (2)	0.3413 (3)	1.3360 (2)	0.0592 (10)
H33	0.3830	0.2783	1.3131	0.071*
C34	0.3650 (3)	0.4757 (4)	1.5213 (3)	0.1001 (17)
H34A	0.3132	0.5016	1.5056	0.150*
H34B	0.4013	0.5230	1.5553	0.150*
H34C	0.3687	0.4160	1.5527	0.150*
N1	−0.13188 (16)	0.2004 (2)	0.18044 (16)	0.0546 (8)
H1A	−0.0849	0.1796	0.2033	0.066*
H1B	−0.1525	0.2043	0.1265	0.066*
N2	−0.13701 (15)	0.2189 (2)	0.31172 (15)	0.0484 (7)
H2A	−0.1583	0.2432	0.3453	0.058*
N3	−0.06606 (15)	0.1716 (2)	0.34324 (16)	0.0466 (6)
N4	0.06536 (14)	0.0494 (2)	0.41195 (15)	0.0426 (6)
N5	0.13947 (15)	0.0238 (2)	0.54691 (15)	0.0478 (7)
N6	0.02709 (18)	0.2052 (3)	0.61998 (18)	0.0678 (9)
N7	0.04052 (19)	0.2341 (3)	0.69742 (19)	0.0737 (10)
N8	0.09920 (16)	0.1767 (3)	0.74714 (16)	0.0575 (8)
N9	0.65336 (16)	0.2177 (2)	0.84265 (16)	0.0593 (8)
H9A	0.6050	0.2340	0.8256	0.071*
H9B	0.6744	0.1998	0.8069	0.071*
N10	0.65883 (14)	0.2492 (2)	0.97685 (15)	0.0485 (7)
H10	0.6813	0.2429	1.0304	0.058*
N11	0.58528 (14)	0.2886 (2)	0.94434 (15)	0.0439 (6)
N12	0.44408 (14)	0.39909 (19)	0.88760 (14)	0.0413 (6)
N13	0.36887 (15)	0.4480 (2)	0.95978 (15)	0.0501 (7)
N14	0.49389 (16)	0.3208 (2)	1.15125 (17)	0.0565 (8)
N15	0.48920 (16)	0.3257 (2)	1.22687 (16)	0.0579 (8)
N16	0.43392 (14)	0.3939 (2)	1.22340 (15)	0.0466 (7)
S1	−0.26434 (5)	0.26826 (9)	0.18941 (5)	0.0621 (3)
S2	0.17525 (6)	−0.06895 (8)	0.41659 (6)	0.0609 (3)
S3	0.78985 (5)	0.18878 (9)	0.96231 (5)	0.0624 (3)
S4	0.32750 (6)	0.49162 (9)	0.78729 (6)	0.0676 (3)
C35	0.0467 (9)	−0.0002 (12)	1.0935 (5)	0.134 (4)	0.5
H35	0.0527	0.0519	1.1309	0.161*	0.5
C36	−0.0348 (7)	0.0759 (10)	0.9677 (9)	0.108 (3)	0.5
H36A	−0.0369	0.0804	0.9104	0.163*	0.5
H36B	−0.0078	0.1321	0.9987	0.163*	0.5
H36C	−0.0867	0.0741	0.9690	0.163*	0.5
C37	0.0126 (7)	−0.0813 (7)	0.9478 (8)	0.115 (4)	0.5
H37A	0.0088	−0.0562	0.8935	0.173*	0.5
H37B	−0.0262	−0.1311	0.9410	0.173*	0.5
H37C	0.0633	−0.1091	0.9749	0.173*	0.5
N17	0.0000	0.0000	1.0000	0.0897 (16)
O1	0.0702 (6)	−0.0692 (9)	1.1073 (6)	0.149 (3)	0.5

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0496 (18)	0.0463 (19)	0.0370 (16)	0.0037 (15)	0.0155 (14)	0.0063 (14)
C2	0.0438 (17)	0.050 (2)	0.0386 (16)	−0.0014 (15)	0.0118 (14)	−0.0023 (15)
C3	0.0374 (16)	0.050 (2)	0.0360 (15)	−0.0007 (14)	0.0108 (13)	0.0000 (14)
C4	0.058 (2)	0.060 (2)	0.0361 (16)	0.0022 (18)	0.0110 (15)	−0.0010 (16)
C5	0.070 (2)	0.061 (2)	0.0421 (18)	0.003 (2)	0.0189 (17)	−0.0055 (17)
C6	0.0429 (17)	0.048 (2)	0.0413 (16)	−0.0011 (15)	0.0107 (14)	−0.0002 (15)
C7	0.0359 (15)	0.052 (2)	0.0364 (15)	−0.0026 (15)	0.0091 (13)	0.0015 (14)
C8	0.0337 (15)	0.063 (2)	0.0392 (16)	−0.0046 (16)	0.0086 (13)	−0.0023 (15)
C9	0.0401 (17)	0.064 (2)	0.0379 (16)	−0.0072 (16)	0.0106 (14)	−0.0042 (16)
C10	0.067 (2)	0.077 (3)	0.0452 (19)	0.005 (2)	0.0089 (18)	0.0041 (19)
C11	0.0456 (19)	0.090 (3)	0.0392 (17)	0.000 (2)	0.0142 (15)	−0.0086 (19)
C12	0.130 (4)	0.172 (6)	0.054 (3)	−0.093 (4)	0.033 (3)	−0.017 (3)
C13	0.124 (4)	0.168 (6)	0.047 (2)	−0.064 (4)	0.031 (3)	−0.003 (3)
C14	0.058 (2)	0.087 (3)	0.048 (2)	0.010 (2)	0.0137 (18)	−0.013 (2)
C15	0.081 (3)	0.065 (3)	0.053 (2)	0.010 (2)	0.005 (2)	−0.012 (2)
C16	0.079 (3)	0.059 (2)	0.049 (2)	0.010 (2)	0.0119 (19)	−0.0013 (18)
C17	0.095 (3)	0.106 (4)	0.048 (2)	0.023 (3)	0.007 (2)	−0.012 (2)
C18	0.0462 (18)	0.061 (2)	0.0389 (16)	0.0017 (16)	0.0200 (14)	−0.0028 (15)
C19	0.0394 (16)	0.058 (2)	0.0328 (15)	−0.0001 (15)	0.0151 (13)	−0.0003 (14)
C20	0.0417 (16)	0.0494 (19)	0.0318 (14)	−0.0009 (15)	0.0152 (13)	−0.0012 (13)
C21	0.059 (2)	0.059 (2)	0.0335 (16)	−0.0019 (18)	0.0212 (15)	0.0017 (15)
C22	0.077 (2)	0.070 (3)	0.0333 (16)	0.000 (2)	0.0186 (17)	0.0023 (17)
C23	0.0462 (18)	0.053 (2)	0.0349 (15)	0.0062 (16)	0.0104 (13)	−0.0017 (15)
C24	0.0353 (15)	0.051 (2)	0.0349 (15)	0.0010 (14)	0.0121 (13)	−0.0024 (14)
C25	0.0352 (15)	0.060 (2)	0.0361 (15)	0.0015 (15)	0.0147 (13)	0.0005 (15)
C26	0.0331 (15)	0.056 (2)	0.0342 (15)	−0.0019 (14)	0.0121 (12)	−0.0017 (14)
C27	0.0515 (19)	0.064 (2)	0.0439 (17)	0.0124 (18)	0.0201 (16)	0.0016 (16)
C28	0.0457 (18)	0.067 (2)	0.0345 (15)	0.0041 (17)	0.0182 (14)	0.0021 (16)
C29	0.099 (3)	0.072 (3)	0.057 (2)	−0.026 (2)	0.043 (2)	−0.010 (2)
C30	0.117 (4)	0.080 (3)	0.068 (3)	−0.026 (3)	0.051 (3)	−0.025 (2)
C31	0.072 (3)	0.088 (3)	0.0421 (19)	0.003 (2)	0.0283 (18)	0.002 (2)
C32	0.083 (3)	0.069 (3)	0.055 (2)	0.016 (2)	0.041 (2)	0.020 (2)
C33	0.078 (3)	0.057 (2)	0.052 (2)	0.013 (2)	0.0341 (19)	0.0091 (18)
C34	0.128 (4)	0.131 (4)	0.059 (3)	−0.007 (4)	0.055 (3)	−0.015 (3)
N1	0.0481 (16)	0.079 (2)	0.0369 (14)	0.0186 (15)	0.0151 (12)	0.0111 (14)
N2	0.0440 (15)	0.0634 (19)	0.0361 (13)	0.0115 (14)	0.0118 (12)	0.0010 (13)
N3	0.0405 (14)	0.0556 (18)	0.0411 (14)	0.0055 (13)	0.0110 (12)	0.0055 (13)
N4	0.0382 (13)	0.0489 (16)	0.0365 (13)	−0.0018 (12)	0.0077 (11)	−0.0007 (12)
N5	0.0401 (14)	0.0602 (18)	0.0395 (14)	0.0012 (13)	0.0093 (12)	−0.0003 (13)
N6	0.0574 (18)	0.097 (3)	0.0430 (16)	0.0199 (18)	0.0102 (14)	−0.0072 (17)
N7	0.0565 (19)	0.112 (3)	0.0465 (17)	0.020 (2)	0.0109 (15)	−0.0134 (18)
N8	0.0457 (16)	0.087 (2)	0.0377 (14)	0.0020 (16)	0.0122 (13)	−0.0061 (15)
N9	0.0418 (15)	0.098 (2)	0.0383 (14)	0.0054 (16)	0.0139 (12)	−0.0152 (15)
N10	0.0391 (14)	0.075 (2)	0.0326 (12)	0.0078 (14)	0.0134 (11)	−0.0015 (13)
N11	0.0361 (13)	0.0590 (18)	0.0361 (13)	0.0038 (13)	0.0121 (11)	−0.0021 (12)
N12	0.0450 (14)	0.0473 (16)	0.0315 (12)	−0.0004 (12)	0.0132 (11)	−0.0010 (11)
N13	0.0471 (15)	0.0671 (19)	0.0358 (13)	0.0093 (14)	0.0139 (12)	0.0004 (13)
N14	0.0513 (16)	0.079 (2)	0.0435 (15)	0.0221 (16)	0.0219 (13)	0.0120 (15)
N15	0.0524 (17)	0.084 (2)	0.0414 (15)	0.0236 (16)	0.0219 (13)	0.0123 (15)
N16	0.0397 (14)	0.0672 (19)	0.0360 (13)	0.0065 (14)	0.0172 (11)	0.0045 (13)
S1	0.0485 (5)	0.0994 (8)	0.0374 (4)	0.0228 (5)	0.0138 (4)	0.0097 (5)
S2	0.0590 (6)	0.0653 (6)	0.0541 (5)	0.0121 (5)	0.0144 (4)	−0.0079 (5)
S3	0.0440 (5)	0.0991 (8)	0.0470 (5)	0.0136 (5)	0.0195 (4)	−0.0007 (5)
S4	0.0719 (6)	0.0821 (8)	0.0406 (5)	0.0197 (6)	0.0090 (4)	0.0082 (5)
C35	0.129 (6)	0.120 (6)	0.132 (6)	−0.007 (6)	0.020 (5)	0.024 (6)
C36	0.103 (8)	0.104 (8)	0.122 (8)	0.017 (7)	0.044 (7)	0.012 (7)
C37	0.120 (8)	0.086 (7)	0.127 (8)	0.009 (6)	0.026 (7)	−0.029 (7)
N17	0.102 (4)	0.081 (4)	0.081 (3)	−0.007 (3)	0.025 (3)	−0.001 (3)
O1	0.139 (7)	0.164 (8)	0.136 (7)	0.033 (7)	0.037 (6)	−0.004 (7)

Geometric parameters (Å, º) top

C1—N1	1.317 (4)	C20—C24	1.385 (4)
C1—N2	1.342 (4)	C20—N12	1.398 (4)
C1—S1	1.684 (3)	C21—C22	1.321 (5)
C2—N3	1.281 (4)	C21—N12	1.392 (4)
C2—C3	1.429 (4)	C22—S4	1.730 (4)
C3—C7	1.389 (4)	C23—N13	1.316 (4)
C3—N4	1.389 (4)	C23—N12	1.357 (4)
C4—C5	1.338 (5)	C23—S4	1.724 (3)
C4—N4	1.399 (4)	C24—N13	1.375 (4)
C5—S2	1.731 (4)	C24—C25	1.459 (4)
C6—N5	1.321 (4)	C25—N14	1.358 (4)
C6—N4	1.367 (4)	C25—C26	1.379 (4)
C6—S2	1.715 (3)	C26—N16	1.352 (4)
C7—N5	1.376 (4)	C26—C27	1.477 (4)
C7—C8	1.449 (4)	C28—C29	1.366 (5)
C8—N6	1.363 (4)	C28—C33	1.368 (5)
C8—C9	1.384 (4)	C28—N16	1.436 (4)
C9—N8	1.355 (4)	C29—C30	1.377 (5)
C9—C10	1.483 (5)	C30—C31	1.373 (6)
C11—C12	1.361 (6)	C31—C32	1.365 (6)
C11—C16	1.363 (5)	C31—C34	1.516 (5)
C11—N8	1.434 (4)	C32—C33	1.395 (5)
C12—C13	1.400 (6)	N2—N3	1.381 (3)
C13—C14	1.353 (7)	N6—N7	1.308 (4)
C14—C15	1.356 (6)	N7—N8	1.358 (4)
C14—C17	1.512 (5)	N10—N11	1.376 (3)
C15—C16	1.382 (5)	N14—N15	1.315 (3)
C18—N9	1.330 (4)	N15—N16	1.360 (4)
C18—N10	1.346 (4)	C35—O1	1.025 (16)
C18—S3	1.679 (3)	C35—N17	1.516 (8)
C19—N11	1.285 (4)	C36—N17	1.235 (12)
C19—C20	1.431 (4)	C37—N17	1.482 (6)

N1—C1—N2	117.4 (3)	C20—C24—C25	128.6 (3)
N1—C1—S1	123.7 (2)	N14—C25—C26	110.0 (3)
N2—C1—S1	118.9 (2)	N14—C25—C24	122.1 (3)
N3—C2—C3	119.4 (3)	C26—C25—C24	127.9 (3)
C7—C3—N4	104.3 (3)	N16—C26—C25	103.1 (3)
C7—C3—C2	132.5 (3)	N16—C26—C27	123.8 (3)
N4—C3—C2	123.1 (3)	C25—C26—C27	133.0 (3)
C5—C4—N4	111.1 (3)	C29—C28—C33	120.5 (3)
C4—C5—S2	113.9 (3)	C29—C28—N16	120.6 (3)
N5—C6—N4	113.1 (3)	C33—C28—N16	118.9 (3)
N5—C6—S2	135.2 (3)	C28—C29—C30	119.5 (4)
N4—C6—S2	111.7 (2)	C31—C30—C29	121.6 (4)
N5—C7—C3	111.8 (3)	C32—C31—C30	118.1 (3)
N5—C7—C8	119.0 (3)	C32—C31—C34	120.6 (4)
C3—C7—C8	129.2 (3)	C30—C31—C34	121.3 (4)
N6—C8—C9	108.7 (3)	C31—C32—C33	121.3 (4)
N6—C8—C7	122.8 (3)	C28—C33—C32	119.0 (4)
C9—C8—C7	128.4 (3)	C1—N2—N3	119.0 (2)
N8—C9—C8	103.4 (3)	C2—N3—N2	116.7 (3)
N8—C9—C10	123.5 (3)	C6—N4—C3	106.8 (2)
C8—C9—C10	133.1 (3)	C6—N4—C4	113.6 (3)
C12—C11—C16	119.7 (3)	C3—N4—C4	139.5 (3)
C12—C11—N8	120.1 (4)	C6—N5—C7	104.1 (3)
C16—C11—N8	120.0 (3)	N7—N6—C8	109.7 (3)
C11—C12—C13	118.7 (5)	N6—N7—N8	106.3 (3)
C14—C13—C12	122.5 (5)	C9—N8—N7	111.9 (3)
C13—C14—C15	117.1 (4)	C9—N8—C11	126.7 (3)
C13—C14—C17	120.5 (4)	N7—N8—C11	121.2 (3)
C15—C14—C17	122.3 (4)	C18—N10—N11	119.6 (2)
C14—C15—C16	122.1 (4)	C19—N11—N10	116.3 (2)
C11—C16—C15	119.8 (4)	C23—N12—C21	114.0 (3)
N9—C18—N10	116.9 (3)	C23—N12—C20	106.6 (2)
N9—C18—S3	122.7 (2)	C21—N12—C20	139.4 (3)
N10—C18—S3	120.4 (2)	C23—N13—C24	103.7 (2)
N11—C19—C20	120.0 (3)	N15—N14—C25	108.3 (3)
C24—C20—N12	103.8 (3)	N14—N15—N16	107.1 (2)
C24—C20—C19	132.5 (3)	C26—N16—N15	111.5 (2)
N12—C20—C19	123.7 (2)	C26—N16—C28	129.0 (3)
C22—C21—N12	111.4 (3)	N15—N16—C28	119.5 (2)
C21—C22—S4	114.0 (2)	C6—S2—C5	89.64 (17)
N13—C23—N12	113.8 (3)	C23—S4—C22	89.28 (16)
N13—C23—S4	135.0 (3)	O1—C35—N17	106.2 (12)
N12—C23—S4	111.2 (2)	C36—N17—C37	121.4 (7)
N13—C24—C20	112.2 (2)	C36—N17—C35	118.7 (8)
N13—C24—C25	119.2 (2)	C37—N17—C35	118.3 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···N5	0.96	2.39	3.074 (4)	128
C27—H27A···N13	0.96	2.41	3.082 (4)	127
N1—H1A···N7ⁱ	0.86	2.62	3.200 (4)	126
N1—H1B···S3ⁱⁱ	0.86	2.62	3.470 (3)	172
N2—H2A···S3ⁱⁱⁱ	0.86	2.65	3.502 (3)	174
N9—H9A···N15ⁱ	0.86	2.34	3.024 (4)	136
N9—H9B···S1^iv	0.86	2.64	3.433 (3)	154
N10—H10···S1^v	0.86	2.55	3.388 (3)	166
C5—H5···O1^vi	0.93	2.59	3.472 (10)	158
C36—H36C···S3^vii	0.96	2.72	3.536 (14)	143
C37—H37B···N6^viii	0.96	2.45	3.111 (11)	126
C37—H37C···S3^ix	0.96	2.75	3.706 (13)	175

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x−1, y, z−1; (iii) x−1, −y+1/2, z−1/2; (iv) x+1, −y+1/2, z+1/2; (v) x+1, y, z+1; (vi) x, y, z−1; (vii) x−1, y, z; (viii) −x, y−1/2, −z+3/2; (ix) −x+1, −y, −z+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.

References

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