Synthesis and crystal structure of 4,6-di­amino-3-(prop-2-en-1-yl)-2-sulfanyl­idene-2,3-di­hydro-1,3,5-triazin-1-ium chloride

Mohamed-Ezzat, R.A.; Kariuki, B.M.; Elgemeie, G.H.

doi:10.1107/S2056989026008182

research communications

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 82| Part 9| September 2026| Pages 1062-1065

https://doi.org/10.1107/S2056989026008182

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Synthesis and crystal structure of 4,6-diamino-3-(prop-2-en-1-yl)-2-sulfanylidene-2,3-dihydro-1,3,5-triazin-1-ium chloride

Reham A. Mohamed-Ezzat,^a ^* Benson M. Kariuki ^b and Galal H. Elgemeie ^c

^aChemistry of Natural & Microbial Products Department, Pharmaceutical and Drug Industries Research Institute, National Research Centre, Cairo, Egypt, ^bSchool of Chemistry, Cardiff University, Main Building, Park Place, Cardiff CF10 3AT, United Kingdom, and ^cDepartment of Chemistry, Faculty of Science, Capital University, Cairo, Egypt
^*Correspondence e-mail: [email protected]

Edited by T. Akitsu, Tokyo University of Science, Japan (Received 15 July 2026; accepted 7 August 2026; online 14 August 2026)

The title structure, C₆H₁₀N₅S⁺·Cl⁻, comprises two independent 4,6-diamino-3-(prop-2-en-1-yl)-2-sulfanylidene-2,3-dihydro-1,3,5-triazin-1-ium cations and two chloride anions. The propene groups assume different conformations in the two cations. The two independent cations are linked by two N—H⋯N hydrogen bonds, forming R²₂(8) motifs. These hydrogen-bonded cation pairs are in turn bridged by the chloride anions through N—H⋯Cl contacts to neighbouring pairs.

Keywords: crystal structure; synthesis; triazinethione; Hirshfeld surface.

CCDC reference: 2570884

1. Chemical context

Triazine is a privileged heterocyclic scaffold for the synthesis of a broad spectrum of pharmacologically bioactive compounds. 1,3,5-Triazine analogs have displayed a wide range of biological potencies, including antifungal, antibacterial, anti-inflammatory, anticancer, anti-Alzheimer's and antiviral properties (Patil et al., 2020 ; Kumawat et al., 2024 ).

Structural modification of the triazine nucleus through substitution at different ring positions provides access to a diverse range of functionalized derivatives suitable for further chemical transformation. The incorporation of an allyl substituent in the triazine core further expands the synthetic utility of triazine-2-thione derivatives.

Building upon the therapeutic significance of the triazine core, the incorporation of allyl-containing functionalities has attracted considerable attention. The allyl moiety is a key structural motif widely incorporated in natural products and bioactive molecules. Integration of an allyl group can modulate molecular flexibility, lipophilicity, and binding interactions, thereby modifying the pharmacological profile of the compound. Besides acting as a protecting or functional group, the allyl scaffold presents potential for further chemical modification via oxidation, cyclization, and various reactions. Numerous allyl-containing analogs have demonstrated a range of biological potencies. Consequently, the allyl fragment has been extensively utilized in medicinal chemistry as a valuable and versatile pharmacophore for the development of novel therapeutic agents (Astrain-Redin et al., 2023 ).

In addition to allyl functionality, sulfur is a prevalent heteroatom in antimetabolic heterocycles (e.g. Mohamed-Ezzat et al., 2026 , Mohamed-Ezzat & Elgemeie, 2023 ; Elgemeie et al. 1999 , 2015 ; Elgemeie & Mohamed, 2014a ,b ; Mustafa et al., 2022 ). Thione functionality serves as a synthetic precursor for the construction of various sulfur containing heterocycles via nucleophilic transformation reactions and tautomeric thione-thiol interconversion. These unique characteristics have established thione-incorporated heterocycles as remarkable structural motifs in drug discovery and development (Katritzky et al., 2008 ; Mustafa et al., 2022).

Following our recently-described approach to the synthesis of triazines (Mohamed-Ezzat & Elgemeie, 2024a ,b ; Mohamed-Ezzat et al., 2024 , 2025 ), particularly triazinethione (Ahmed et al. 2026 ), and in a continuation of our research to explore the synthetic potential of this scaffold and to expand the chemical diversity of triazine systems by incorporating the allyl and thione functionalities into the triazine scaffold, we now report the synthesis and structure of the title compound (I).

2. Structural commentary

The asymmetric unit of (I) contains two independent 4,6-diamino-3-(prop-2-en-1-yl)-2-sulfanylidene-2,3-dihydro-1,3,5-triazin-1-ium cations and two chloride anions (Fig. 1). Each cation consists of a diaminotriazinethione (DTT) group (C1–C3/N1–N5/S1) and C7–C9/N6–N10/S2 for the two independent cations, here referred to as c1 and c2, linked to a propene group (C4–C6 and C10–C12 for c1 and c2, respectively). The DTT groups are almost planar in the two cations but the orientations of the propene groups differ with torsion angles N1—C4—C5—C6 and N6—C10—C11—C12 of 6.9 (6)° and 147.5 (3)° for c1 and c2, respectively. The corresponding bond lengths and angles are similar in two cations apart from the propene groups where C4—C5 [1.470 (5) Å] is slightly shorter than C10—C11 [1.486 (4) Å] and the angle C4—C5—C6 [127.3 (3)°] is greater than C10—C11—C12 [124.2 (4)°]. One nitrogen atom of each independent triazine ring (N2 in c1 and N7 in c2) is protonated. The C—N bond lengths associated with the protonated nitrogen atoms (C1—N2, C2—N2, C8—N7 and C7—N7) are in the range 1.355 (3) to 1.362 (3) Å. In contrast, the bond lengths (C2—N3, C3—N3, C8—N8, C9—N8) for the unprotonated nitrogen atoms (N3 for c1 and N8 for c2) are shorter, being in the range 1.328 (3)–1.331 (3) Å. The associated bond angles for the protonated nitrogen atoms [C1—N2–C2 = 123.7 (2) in c1 and C7—N7—C8 = 123.7 (2)° for c2] are greater than those for the unprotonated atoms [C2—N3—C3 = 117.08 (19)° in c1 and C8—N8—C9 = 117.41 (19)° in c2]. The diaminotriazinethione groups in the structure of cis(4,6-diamino-2-thiono-1H-(1,3,5)triazinium)aquabis(oxalato-O,O′)dioxouranium(VI) N-cyanoguanidine (Serezhkina et al., 2007 ) show a similar contrast in the geometry around the protonated and unprotonated nitrogen atoms.

Figure 1
The asymmetric unit of the title compound showing displacement ellipsoids at the 50% probability level. Hydrogen bonds are indicated by dashed lines

3. Supramolecular features

In the crystal, the two independent cations are linked by a pair of N—H⋯N hydrogen bonds, namely N10—H10C⋯N3 and N5—H5A⋯N8, in which the amino groups are the donors and the triazine nitrogen atoms are the acceptors, forming R₂²(8) motifs (Table 1, Fig. 2). The resultant hydrogen-bonded cation pairs are bridged by chloride anions through N—H⋯Cl contacts to neighbouring pairs. Each of the two independent chloride anions accepts four N—H⋯Cl contacts of which three are from amino groups and one from a triazine N—H group.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10B⋯S1ⁱ	0.97	3.01	3.675 (3)	127
N4—H4C⋯Cl2ⁱⁱ	0.85 (1)	2.34 (1)	3.183 (2)	169 (3)
N4—H4D⋯Cl1	0.86 (1)	2.44 (2)	3.243 (2)	155 (2)
N5—H5A⋯N8	0.86 (1)	2.21 (1)	3.070 (3)	172 (3)
N5—H5B⋯Cl1ⁱⁱⁱ	0.86 (1)	2.36 (2)	3.148 (2)	153 (3)
N9—H9A⋯Cl1ⁱⁱⁱ	0.86 (1)	2.47 (1)	3.314 (2)	171 (3)
N9—H9B⋯Cl2	0.86 (1)	2.64 (2)	3.400 (2)	148 (3)
N10—H10C⋯N3	0.86 (1)	2.22 (1)	3.056 (3)	163 (3)
N10—H10D⋯Cl2ⁱⁱ	0.86 (1)	2.42 (2)	3.142 (2)	143 (3)
N7—H7⋯Cl2	0.83 (3)	2.34 (3)	3.131 (2)	161 (3)
N2—H2⋯Cl1	0.86 (4)	2.33 (4)	3.144 (2)	158 (3)
Symmetry codes: (i) ; (ii) $[x-{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

Figure 2
A segment of the crystal structure viewed along the b-axis direction with N—H⋯N and N—H⋯Cl hydrogen-bond interactions shown as dotted lines. For clarity, only one layer of the structure is depicted.

The Hirshfeld surfaces obtained using CrystalExplorer (Spackman et al., 2021 ) illustrate the similarities in the closest intermolecular contacts for the two independent cations (Fig. 3a for c1 and Fig. 3c for c2). Surface coverage analysis by element shows H (68.3%), N (11.4%), S (12.9%) and C (7.4%) for c1 and H (66.6%), N (12.1%), S (12.7%) and C (8.5%) for c2. The results show that the independent cations are involved in similar intermolecular contacts with their neighbours. However, the intermolecular contacts are not identical, as shown by examination of the two-dimensional fingerprint plots for cations c1 (Fig. 3b) and c2 (Fig. 3d).

Figure 3
(a) The d_norm Hirshfeld surface of cation c1 showing N—H⋯N and N—H⋯Cl hydrogen bond contacts as green dashed lines. (b) The Hirshfeld surface two-dimensional fingerprint plot for c1 with intermolecular contacts involving nitrogen atoms highlighted in blue. (c) The d_norm Hirshfeld surface of cation c2 showing N—H⋯N and N—H⋯Cl hydrogen-bond contacts as green dashed lines. (d) The Hirshfeld surface two-dimensional fingerprint plots for c2 with intermolecular contacts involving nitrogen atoms highlighted in blue.

4. Database survey

A search of the Cambridge Structural Database (CSD, updated to April 2026; Groom, et al., 2016 ) for the DTT group gave two hits. In 4,6-diamino-1-cyclohexyl-1,3,5-triazine-2(1H)-thione monohydrate (CSD refcode AZAZUA; Ahmed et al., 2026), the DTT group is bonded to a cyclohexane ring and hydrogen bonded by water. Bis(4,6-diamino-2-thiono-1H-(1,3,5)triazinium) aquabis(oxalato-O,O′)dioxouranium(VI) N-cyanoguanidine (QELQAA) (Serezhkina et al., 2007) has two independent DTT groups and displays an R₂²(8) motif akin to that observed in the title compound.

5. Synthesis and crystallization

The title compound was obtained, as shown in Fig. 4, from the reaction of cyanamide (1) with allylisothio-cyanate (2) in ethanol in the presence of potassium hydroxide at room temperature for 30 min. The reaction mixture was then poured on water and hydrolysed using hydrochloric acid, , then recrystallized from aqueous solution to afford the title compound 3.

Figure 4
Reaction scheme for the formation of the title compound.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The N-bound H atoms were freely refined. Other H atoms were place in idealized position and refined using a riding model with U_iso(H) = 1.2 or 1.5U_eq(C).

Table 2
Experimental details

Crystal data
Chemical formula	C₆H₁₀N₅S⁺·Cl⁻
M_r	219.70
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	296
a, b, c (Å)	17.2243 (4), 12.2458 (4), 18.9429 (5)
V (Å³)	3995.54 (19)
Z	16
Radiation type	Cu Kα
μ (mm⁻¹)	5.05
Crystal size (mm)	0.14 × 0.09 × 0.07

Data collection
Diffractometer	SuperNova, Dual, Cu at home/near, Atlas
Absorption correction	Gaussian (CrysAlis PRO; Rigaku OD, 2026 )
T_min, T_max	0.605, 0.799
No. of measured, independent and observed [I > 2σ(I)] reflections	14045, 3733, 3093
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.610

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.125, 1.06
No. of reflections	3733
No. of parameters	275
No. of restraints	8
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.61
Computer programs: CrysAlis PRO (Rigaku OD, 2026), SHELXT (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b ), ORTEP-3 for Windows (Farrugia, 2012 ) and Mercury (Macrae et al., 2020 )..

Supporting information

CCDC reference: 2570884

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989026008182/jp2031sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989026008182/jp2031Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989026008182/jp2031Isup3.cml

checkCIF report

Computing details top

4,6-Diamino-3-(prop-2-en-1-yl)-2-sulfanylidene-2,3-dihydro-1,3,5-triazin-1-ium chloride top

Crystal data top

C₆H₁₀N₅S⁺·Cl⁻	D_x = 1.461 Mg m⁻³
M_r = 219.70	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, Pbca	Cell parameters from 6530 reflections
a = 17.2243 (4) Å	θ = 4.7–70.0°
b = 12.2458 (4) Å	µ = 5.05 mm⁻¹
c = 18.9429 (5) Å	T = 296 K
V = 3995.54 (19) Å³	Block, colourless
Z = 16	0.14 × 0.09 × 0.07 mm
F(000) = 1824

Data collection top

SuperNova, Dual, Cu at home/near, Atlas diffractometer	3093 reflections with I > 2σ(I)
Detector resolution: 10.5082 pixels mm^-1	R_int = 0.037
ω scans	θ_max = 70.2°, θ_min = 4.7°
Absorption correction: gaussian (CrysAlisPro; Rigaku OD, 2026)	h = −20→20
T_min = 0.605, T_max = 0.799	k = −10→14
14045 measured reflections	l = −15→22
3733 independent reflections

Refinement top

Refinement on F²	8 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.125	w = 1/[σ²(F_o²) + (0.0689P)² + 1.5902P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
3733 reflections	Δρ_max = 0.30 e Å⁻³
275 parameters	Δρ_min = −0.61 e Å⁻³

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

	x	y	z	U_iso*/U_eq
C1	0.55186 (14)	0.1964 (2)	0.56942 (12)	0.0416 (5)
C2	0.47990 (13)	0.33028 (18)	0.50421 (11)	0.0339 (5)
C3	0.60373 (13)	0.29380 (19)	0.47078 (11)	0.0371 (5)
C4	0.68763 (15)	0.1641 (2)	0.53638 (15)	0.0512 (6)
H4A	0.728925	0.212943	0.521743	0.061*
H4B	0.693712	0.151018	0.586580	0.061*
C5	0.6966 (2)	0.0598 (3)	0.4988 (2)	0.0726 (9)
H5	0.745325	0.027360	0.501020	0.087*
C6	0.6451 (3)	0.0090 (4)	0.4635 (3)	0.0966 (13)
H6A	0.595291	0.037773	0.459533	0.116*
H6B	0.657227	−0.056859	0.441733	0.116*
C7	0.64075 (13)	0.6258 (2)	0.19641 (12)	0.0396 (5)
C8	0.70801 (13)	0.47868 (19)	0.25284 (11)	0.0367 (5)
C9	0.58648 (13)	0.5205 (2)	0.29058 (11)	0.0367 (5)
C10	0.51400 (15)	0.6800 (2)	0.24412 (14)	0.0515 (6)
H10A	0.531011	0.751773	0.228941	0.062*
H10B	0.495489	0.686428	0.292308	0.062*
C11	0.44879 (18)	0.6440 (3)	0.19837 (17)	0.0664 (8)
H11	0.460874	0.606170	0.157231	0.080*
C12	0.3768 (2)	0.6616 (4)	0.2120 (2)	0.0829 (11)
H12A	0.362798	0.699195	0.252670	0.100*
H12B	0.338726	0.636846	0.181065	0.100*
Cl1	0.32306 (3)	0.26965 (5)	0.63015 (3)	0.04541 (18)
Cl2	0.85800 (3)	0.55220 (5)	0.11729 (3)	0.04427 (18)
N1	0.61244 (11)	0.21857 (16)	0.52437 (10)	0.0375 (4)
N2	0.48631 (12)	0.25456 (17)	0.55655 (11)	0.0408 (5)
N3	0.53805 (11)	0.34843 (16)	0.45961 (9)	0.0364 (4)
N4	0.41451 (11)	0.38403 (18)	0.50004 (11)	0.0420 (5)
N5	0.66255 (12)	0.3135 (2)	0.42838 (12)	0.0469 (5)
N6	0.58105 (11)	0.60458 (17)	0.24269 (10)	0.0374 (4)
N7	0.70284 (12)	0.55877 (17)	0.20332 (11)	0.0403 (4)
N8	0.64983 (11)	0.45932 (16)	0.29709 (10)	0.0374 (4)
N9	0.77166 (13)	0.4203 (2)	0.25436 (13)	0.0532 (6)
N10	0.52738 (13)	0.4994 (2)	0.33153 (12)	0.0504 (6)
S1	0.55368 (5)	0.10760 (7)	0.63339 (4)	0.0687 (3)
S2	0.63898 (5)	0.72293 (7)	0.13656 (4)	0.0632 (2)
H4C	0.4060 (17)	0.4314 (18)	0.4679 (11)	0.051 (8)*
H4D	0.3786 (12)	0.366 (2)	0.5294 (11)	0.042 (7)*
H5A	0.6553 (19)	0.357 (2)	0.3935 (11)	0.054 (9)*
H5B	0.7048 (11)	0.276 (2)	0.4250 (17)	0.060 (9)*
H9A	0.7791 (18)	0.3688 (18)	0.2842 (13)	0.055 (8)*
H9B	0.8075 (15)	0.433 (3)	0.2238 (14)	0.068 (10)*
H10C	0.5313 (19)	0.4462 (17)	0.3609 (13)	0.053 (9)*
H10D	0.4852 (12)	0.537 (2)	0.3300 (17)	0.065 (10)*
H7	0.7391 (19)	0.570 (2)	0.1757 (16)	0.053 (8)*
H2	0.446 (2)	0.242 (3)	0.5818 (19)	0.073 (11)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0452 (13)	0.0414 (13)	0.0383 (11)	0.0041 (10)	−0.0003 (10)	0.0004 (10)
C2	0.0358 (11)	0.0349 (12)	0.0309 (10)	−0.0011 (9)	−0.0007 (8)	−0.0004 (9)
C3	0.0356 (11)	0.0414 (12)	0.0343 (11)	0.0005 (9)	−0.0027 (9)	−0.0055 (9)
C4	0.0384 (13)	0.0595 (17)	0.0559 (15)	0.0070 (12)	−0.0062 (11)	0.0073 (13)
C5	0.0529 (17)	0.0582 (19)	0.107 (3)	0.0196 (15)	0.0048 (18)	0.0043 (19)
C6	0.101 (3)	0.070 (2)	0.118 (3)	0.017 (2)	0.001 (3)	−0.031 (2)
C7	0.0375 (12)	0.0419 (13)	0.0395 (11)	−0.0004 (10)	−0.0023 (9)	0.0003 (10)
C8	0.0332 (11)	0.0403 (12)	0.0367 (11)	0.0019 (9)	0.0012 (9)	0.0020 (9)
C9	0.0319 (11)	0.0445 (13)	0.0336 (11)	−0.0006 (9)	−0.0013 (8)	−0.0022 (9)
C10	0.0466 (14)	0.0563 (16)	0.0515 (14)	0.0168 (12)	0.0022 (11)	0.0026 (12)
C11	0.0511 (16)	0.090 (2)	0.0584 (17)	0.0188 (16)	−0.0088 (13)	0.0073 (16)
C12	0.0570 (18)	0.107 (3)	0.085 (2)	0.0038 (19)	−0.0070 (17)	0.036 (2)
Cl1	0.0348 (3)	0.0570 (4)	0.0445 (3)	−0.0086 (2)	0.0021 (2)	0.0004 (3)
Cl2	0.0355 (3)	0.0570 (4)	0.0402 (3)	0.0050 (2)	0.0046 (2)	−0.0017 (2)
N1	0.0359 (9)	0.0390 (10)	0.0375 (9)	0.0042 (8)	−0.0031 (8)	0.0002 (8)
N2	0.0376 (10)	0.0451 (11)	0.0396 (10)	0.0020 (9)	0.0051 (9)	0.0084 (9)
N3	0.0326 (9)	0.0436 (11)	0.0330 (9)	0.0015 (8)	0.0014 (7)	0.0026 (8)
N4	0.0357 (10)	0.0507 (13)	0.0395 (10)	0.0052 (9)	0.0042 (8)	0.0088 (9)
N5	0.0350 (10)	0.0612 (14)	0.0444 (11)	0.0069 (10)	0.0058 (9)	0.0069 (10)
N6	0.0328 (9)	0.0448 (11)	0.0347 (9)	0.0047 (8)	−0.0012 (7)	0.0002 (8)
N7	0.0331 (10)	0.0477 (12)	0.0401 (10)	0.0012 (9)	0.0071 (8)	0.0072 (9)
N8	0.0332 (9)	0.0413 (11)	0.0375 (9)	0.0028 (8)	0.0033 (8)	0.0044 (8)
N9	0.0400 (11)	0.0607 (15)	0.0589 (13)	0.0139 (10)	0.0140 (10)	0.0191 (11)
N10	0.0363 (11)	0.0702 (16)	0.0448 (12)	0.0084 (11)	0.0094 (9)	0.0136 (11)
S1	0.0762 (5)	0.0689 (5)	0.0611 (4)	0.0200 (4)	0.0068 (4)	0.0251 (4)
S2	0.0600 (5)	0.0636 (5)	0.0660 (5)	0.0049 (3)	0.0037 (3)	0.0287 (4)

Geometric parameters (Å, º) top

C1—N2	1.357 (3)	C8—N7	1.360 (3)
C1—N1	1.375 (3)	C9—N10	1.306 (3)
C1—S1	1.629 (2)	C9—N8	1.329 (3)
C2—N4	1.307 (3)	C9—N6	1.375 (3)
C2—N3	1.329 (3)	C10—N6	1.479 (3)
C2—N2	1.362 (3)	C10—C11	1.486 (4)
C3—N5	1.315 (3)	C10—H10A	0.9700
C3—N3	1.331 (3)	C10—H10B	0.9700
C3—N1	1.379 (3)	C11—C12	1.284 (5)
C4—C5	1.470 (5)	C11—H11	0.9300
C4—N1	1.475 (3)	C12—H12A	0.9300
C4—H4A	0.9700	C12—H12B	0.9300
C4—H4B	0.9700	N2—H2	0.86 (4)
C5—C6	1.273 (6)	N4—H4C	0.854 (10)
C5—H5	0.9300	N4—H4D	0.860 (10)
C6—H6A	0.9300	N5—H5A	0.861 (10)
C6—H6B	0.9300	N5—H5B	0.861 (10)
C7—N7	1.355 (3)	N7—H7	0.83 (3)
C7—N6	1.376 (3)	N9—H9A	0.857 (10)
C7—S2	1.643 (2)	N9—H9B	0.860 (10)
C8—N9	1.309 (3)	N10—H10C	0.859 (10)
C8—N8	1.328 (3)	N10—H10D	0.860 (10)

N2—C1—N1	114.6 (2)	C11—C10—H10B	108.9
N2—C1—S1	120.01 (19)	H10A—C10—H10B	107.8
N1—C1—S1	125.36 (19)	C12—C11—C10	124.2 (4)
N4—C2—N3	121.8 (2)	C12—C11—H11	117.9
N4—C2—N2	117.2 (2)	C10—C11—H11	117.9
N3—C2—N2	121.0 (2)	C11—C12—H12A	120.0
N5—C3—N3	117.7 (2)	C11—C12—H12B	120.0
N5—C3—N1	119.2 (2)	H12A—C12—H12B	120.0
N3—C3—N1	123.0 (2)	C1—N1—C3	120.4 (2)
C5—C4—N1	114.2 (2)	C1—N1—C4	118.8 (2)
C5—C4—H4A	108.7	C3—N1—C4	120.8 (2)
N1—C4—H4A	108.7	C1—N2—C2	123.7 (2)
C5—C4—H4B	108.7	C1—N2—H2	119 (2)
N1—C4—H4B	108.7	C2—N2—H2	118 (2)
H4A—C4—H4B	107.6	C2—N3—C3	117.08 (19)
C6—C5—C4	127.3 (3)	C2—N4—H4C	122 (2)
C6—C5—H5	116.4	C2—N4—H4D	117.1 (19)
C4—C5—H5	116.4	H4C—N4—H4D	121 (3)
C5—C6—H6A	120.0	C3—N5—H5A	118 (2)
C5—C6—H6B	120.0	C3—N5—H5B	127 (2)
H6A—C6—H6B	120.0	H5A—N5—H5B	113 (3)
N7—C7—N6	114.5 (2)	C9—N6—C7	120.71 (19)
N7—C7—S2	121.33 (18)	C9—N6—C10	120.56 (19)
N6—C7—S2	124.21 (18)	C7—N6—C10	118.5 (2)
N9—C8—N8	121.4 (2)	C7—N7—C8	123.7 (2)
N9—C8—N7	117.6 (2)	C7—N7—H7	116 (2)
N8—C8—N7	121.0 (2)	C8—N7—H7	120 (2)
N10—C9—N8	118.3 (2)	C8—N8—C9	117.41 (19)
N10—C9—N6	119.1 (2)	C8—N9—H9A	123 (2)
N8—C9—N6	122.6 (2)	C8—N9—H9B	119 (2)
N6—C10—C11	113.2 (2)	H9A—N9—H9B	118 (3)
N6—C10—H10A	108.9	C9—N10—H10C	118 (2)
C11—C10—H10A	108.9	C9—N10—H10D	122 (2)
N6—C10—H10B	108.9	H10C—N10—H10D	120 (3)

N1—C4—C5—C6	−6.9 (6)	N1—C3—N3—C2	2.0 (3)
N6—C10—C11—C12	147.5 (3)	N10—C9—N6—C7	−176.9 (2)
N2—C1—N1—C3	−0.7 (3)	N8—C9—N6—C7	3.1 (3)
S1—C1—N1—C3	178.38 (18)	N10—C9—N6—C10	8.6 (3)
N2—C1—N1—C4	176.7 (2)	N8—C9—N6—C10	−171.4 (2)
S1—C1—N1—C4	−4.3 (3)	N7—C7—N6—C9	−0.6 (3)
N5—C3—N1—C1	−180.0 (2)	S2—C7—N6—C9	178.94 (18)
N3—C3—N1—C1	0.1 (3)	N7—C7—N6—C10	174.0 (2)
N5—C3—N1—C4	2.7 (3)	S2—C7—N6—C10	−6.4 (3)
N3—C3—N1—C4	−177.2 (2)	C11—C10—N6—C9	−91.0 (3)
C5—C4—N1—C1	90.8 (3)	C11—C10—N6—C7	94.4 (3)
C5—C4—N1—C3	−91.8 (3)	N6—C7—N7—C8	−1.9 (3)
N1—C1—N2—C2	−0.9 (3)	S2—C7—N7—C8	178.58 (19)
S1—C1—N2—C2	180.00 (19)	N9—C8—N7—C7	−179.2 (2)
N4—C2—N2—C1	−176.7 (2)	N8—C8—N7—C7	2.0 (4)
N3—C2—N2—C1	3.1 (4)	N9—C8—N8—C9	−178.2 (2)
N4—C2—N3—C3	176.3 (2)	N7—C8—N8—C9	0.5 (3)
N2—C2—N3—C3	−3.5 (3)	N10—C9—N8—C8	177.0 (2)
N5—C3—N3—C2	−177.9 (2)	N6—C9—N8—C8	−3.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10B···S1ⁱ	0.97	3.01	3.675 (3)	127
N4—H4C···Cl2ⁱⁱ	0.85 (1)	2.34 (1)	3.183 (2)	169 (3)
N4—H4D···Cl1	0.86 (1)	2.44 (2)	3.243 (2)	155 (2)
N5—H5A···N8	0.86 (1)	2.21 (1)	3.070 (3)	172 (3)
N5—H5B···Cl1ⁱⁱⁱ	0.86 (1)	2.36 (2)	3.148 (2)	153 (3)
N9—H9A···Cl1ⁱⁱⁱ	0.86 (1)	2.47 (1)	3.314 (2)	171 (3)
N9—H9B···Cl2	0.86 (1)	2.64 (2)	3.400 (2)	148 (3)
N10—H10C···N3	0.86 (1)	2.22 (1)	3.056 (3)	163 (3)
N10—H10D···Cl2ⁱⁱ	0.86 (1)	2.42 (2)	3.142 (2)	143 (3)
N7—H7···Cl2	0.83 (3)	2.34 (3)	3.131 (2)	161 (3)
N2—H2···Cl1	0.86 (4)	2.33 (4)	3.144 (2)	158 (3)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x−1/2, y, −z+1/2; (iii) x+1/2, −y+1/2, −z+1.

Acknowledgements

We are grateful for support by the National Research Centre, Cairo, Egypt and Cardiff University, UK and Capital University, Helwan, Egypt.

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