Synthesis and crystal structure of 4,6-di­amino-1-cyclo­hexyl-1,3,5-triazine-2(1H)-thione monohydrate

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

doi:10.1107/S2056989026002240

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ISSN: 2056-9890

Volume 82| Part 4| April 2026| Pages 341-344

https://doi.org/10.1107/S2056989026002240

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Synthesis and crystal structure of 4,6-diamino-1-cyclohexyl-1,3,5-triazine-2(1H)-thione monohydrate

Ebtsam A. Ahmed,^a,^b Benson M. Kariuki,^c Reham A. Mohamed-Ezzat,^d ^* Rasha A. Azzam ^a and Galal H. Elgemeie ^a

^aDepartment of Chemistry, Faculty of Science, Capital University, Helwan, Egypt, ^bDepartment of Chemistry, College of Science, King Faisal University, 31982, Al-Ahsa, Saudi Arabia, ^cSchool of Chemistry, Cardiff University, Main Building, Park Place, Cardiff CF10, 3AT, United Kingdom, and ^dChemistry of Natural & Microbial Products Department, Pharmaceutical and Drug Industries Research Institute, National Research Centre, Cairo, Egypt
^*Correspondence e-mail: [email protected]

Edited by T. Akitsu, Tokyo University of Science, Japan (Received 17 February 2026; accepted 28 February 2026; online 5 March 2026)

In the crystal structure of the title compound, C₉H₁₅N₅S·H₂O, the diaminotriazinethione (DTT) moiety and water molecules are hydrogen bonded to form ribbons. In the ribbon, each water molecule accepts a pair of N—H⋯O bonds from the DTT moieties of two adjacent molecules and donates one O—H⋯N bond to a third DTT moiety. The ribbons are stacked and linked through O—H⋯N interactions. The cyclohexane moieties are pendant to the ribbons forming a layer-like structure.

Keywords: synthesis; crystal structure; triazinethione.

CCDC reference: 2531186

1. Chemical context

Triazines constitute one of the most noteworthy heterocyclic scaffolds for drug discovery as a result of their structural significance and broad-spectrum biological potencies (Kciuk et al., 2023 ; Gornowicz et al., 2020 ; Mohamed-Ezzat & Elgemeie, 2024a ; Abdallah et al., 2021 ). Numerous triazine-containing drugs for treatment of many diseases have been approved by the FDA, including decitabine, cycloguanil, altretamine, bimiralisib, almitrine, lamotrigine and triazavirin (Ali et al., 2025 ).

The discovery of sulfur-based therapies has also been an important development of the pharmaceutical industry and sulfur-derived functional groups are present in a wide variety of natural products and pharmaceuticals. Sulfur continues to be the predominant heteroatom in many antimetabolic heterocycles and in a range of FDA-approved drugs (Mohamed-Ezzat et al., 2022 , 2023 ; Feng et al., 2016 ; Elgemeie et al., 1992 , 1999 ).

The results presented here were obtained in continuation of our program in the synthesis of heterocycles utilizing cyanocarboimidodithioate as a key precursor. This highly reactive compound has been utilized effectively in the synthesis of various heterocycles (Elgemeie & Mohamed, 2014a ,b ; Elgemeie et al., 2015 ; Mohamed-Ezzat & Elgemeie, 2023 , 2024a; Mohamed-Ezzat et al., 2024 ). We have also recently synthesized numerous triazines via novel approaches (Mohamed-Ezzat et al., 2024b , 2025 ).

The incorporation of sulfur functionalities into molecules containing the triazine ring system combines two privileged scaffolds. Combination of the two important pharmacophores in the framework is a strategy for the development of potentially novel therapeutic agents. Herein, the novel triazinethione was synthesized via reaction of cyclohexylisothiocyanate with cyanamide in the presence of potassium hydroxide at room temperature as depicted in Fig. 1.

Figure 1
Reaction scheme showing the synthesis of compound 5.

2. Structural commentary

The compound crystallizes in the orthorhombic, Pbca space group. The asymmetric unit contains a molecule of 4,6-diamino-1-cyclohexyl-1,3,5-triazine-2(1H)-thione (5) and a water molecule (Fig. 2). The molecule of 5 consists of a cyclohexane ring (C1–C6) and a diaminotriazinethione (DTT) moiety (C7–C9, N1–N5, S1). In the molecule, the least-squares plane through the cyclohexane ring is twisted from the plane through the DTT moiety by a dihedral angle of 72.07 (10)°.

Figure 2
The asymmetric unit of the crystal structure of 5·H₂O showing displacement ellipsoids at the 50% probability level.

The cyclohexane ring is in a chair conformation. The triazine ring of the DTT moiety is slightly curved as indicated by displacement of atoms C9 and N1 to the same side of the ring, away from the plane through atoms C7, C8, N2, N3, by 0.125 (3) and 0.161 (3) Å, respectively.

3. Supramolecular features

In the crystal structure, the DTT moieties and water molecules are hydrogen bonded to form ribbons propagated in the [100] direction (Table 1, Fig. 3a). In the ribbon, each water molecule accepts a pair of N—H⋯O bonds from the DTT moieties of two adjacent molecules and donates one O—H⋯N bond to a third DTT moiety. Additional N—H⋯N and N—H⋯S hydrogen bonds also occur in the ribbon. The ribbons are stacked in the [010] direction in the crystal and they are linked through O—H⋯N interactions (Fig. 3b). Additionally, a weak O-H⋯S hydrogen bond connects ribbons in the b-axis direction. The cyclohexane moieties are pendant to the ribbons and hence the structure is layer-like.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4C⋯N3ⁱ	0.86 (3)	2.62 (3)	3.151 (3)	121 (2)
N4—H4C⋯O1	0.86 (3)	2.53 (3)	3.239 (3)	140 (2)
N4—H4D⋯S1ⁱ	0.87 (3)	2.52 (3)	3.313 (2)	152 (2)
N5—H5C⋯O1ⁱⁱ	0.89 (4)	2.09 (4)	2.967 (3)	167 (3)
N5—H5D⋯O1ⁱⁱⁱ	0.83 (3)	2.29 (3)	3.094 (3)	164 (3)
O1—H1O⋯N2	0.82 (4)	2.19 (3)	2.949 (3)	153 (3)
O1—H2O⋯N3^iv	0.85 (3)	2.61 (3)	3.325 (3)	142 (3)
O1—H2O⋯S1^iv	0.85 (3)	2.79 (3)	3.574 (2)	153 (3)
Symmetry codes: (i) ; (ii) ; (iii) ; (iv) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

Figure 3
Segments of the crystal structure of 5·H₂O showing (a) a ribbon formed through hydrogen bonding and (b) the stacking of ribbons viewed down the a axis.

4. Database survey

A search of the CSD (version 6.00, November 2025; Groom et al., 2016 ) for crystal structures containing the diaminotriazinethione moiety revealed 6-(benzylsulfanyl)-1,3,5-triazine-2,4-diamine (COFPEW; Liu et al., 2024 ) and bis(4,6-diamino-2-thiono-1H-(1,3,5)triazinium) aquabis(oxalato-O,O′)dioxouranium(VI) N-cyanoguanidine (QELQAA, QELQAA01); Serezhkina et al., 2007 ). COFPEW has three molecules in the asymmetric unit with the methylbenzene moieties linked to the DTT through the S atoms. The planes through the phenyl rings are twisted from the DTT planes by dihedral angles in the range 70–83°, comparable to that observed for the cyclohexane ring in the title compound. QELQAA(01) is a metal complex containing separate DTT units.

5. Synthesis and crystallization

The title compound was obtained, as depicted in Fig. 1, starting from the reaction of cyclohexylisothiocyanate (1) with cyanamide (2) in the presence of potassium hydroxide in ethanol at room temperature for 30 min. The reaction mixture was then poured into water and hydrolysed using hydrochloric acid to give the title compound 5 as colorless crystals of various shapes which were then crystallized from water to give needles.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The cyclohexane H atoms were inserted in idealized positions and refined using a riding model with U_iso(H) = U_eq(C).

Table 2
Experimental details

Crystal data
Chemical formula	C₉H₁₅N₅S·H₂O
M_r	243.33
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	293
a, b, c (Å)	7.0790 (4), 9.9029 (6), 33.0489 (19)
V (Å³)	2316.8 (2)
Z	8
Radiation type	Mo Kα
μ (mm⁻¹)	0.27
Crystal size (mm)	0.48 × 0.18 × 0.07

Data collection
Diffractometer	SuperNova, Dual, Cu at home/near, Atlas
Absorption correction	Gaussian (CrysAlis PRO; Rigaku, 2024 )
T_min, T_max	0.545, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	20982, 3038, 2038
R_int	0.076
(sin θ/λ)_max (Å⁻¹)	0.697

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.136, 1.09
No. of reflections	3038
No. of parameters	167
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.23
Computer programs: CrysAlis PRO (Rigaku, 2024), SHELXT (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b ), ORTEP-3 for Windows and WinGX (Farrugia, 2012 ).

Supporting information

CCDC reference: 2531186

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989026002240/jp2026sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989026002240/jp2026Isup3.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989026002240/jp2026Isup3.cml

checkCIF report

Computing details top

4,6-Diamino-1-cyclohexyl-1,3,5-triazine-2(1H)-thione monohydrate top

Crystal data top

C₉H₁₅N₅S·H₂O	D_x = 1.395 Mg m⁻³
M_r = 243.33	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 5364 reflections
a = 7.0790 (4) Å	θ = 3.7–28.9°
b = 9.9029 (6) Å	µ = 0.27 mm⁻¹
c = 33.0489 (19) Å	T = 293 K
V = 2316.8 (2) Å³	Needle, colourless
Z = 8	0.48 × 0.18 × 0.07 mm
F(000) = 1040

Data collection top

SuperNova, Dual, Cu at home/near, Atlas diffractometer	2038 reflections with I > 2σ(I)
Detector resolution: 10.5082 pixels mm^-1	R_int = 0.076
ω scans	θ_max = 29.7°, θ_min = 3.1°
Absorption correction: gaussian (CrysAlisPro; Rigaku, 2024)	h = −9→8
T_min = 0.545, T_max = 1.000	k = −12→13
20982 measured reflections	l = −43→45
3038 independent reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.056	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.136	w = 1/[σ²(F_o²) + (0.0441P)² + 1.2175P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max < 0.001
3038 reflections	Δρ_max = 0.35 e Å⁻³
167 parameters	Δρ_min = −0.23 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	0.3805 (3)	0.5848 (2)	0.34849 (6)	0.0293 (5)
H1	0.265632	0.575172	0.332190	0.035*
C2	0.4606 (3)	0.4428 (2)	0.35160 (7)	0.0353 (5)
H2A	0.373765	0.385546	0.366454	0.042*
H2B	0.579721	0.444867	0.366096	0.042*
C3	0.4910 (4)	0.3861 (3)	0.30934 (8)	0.0466 (6)
H3A	0.552642	0.298912	0.311366	0.056*
H3B	0.369353	0.372666	0.296438	0.056*
C4	0.6104 (4)	0.4792 (3)	0.28334 (8)	0.0537 (7)
H4A	0.737921	0.482095	0.294053	0.064*
H4B	0.616642	0.443384	0.256053	0.064*
C5	0.5306 (4)	0.6210 (3)	0.28206 (7)	0.0470 (6)
H5A	0.409229	0.619649	0.268428	0.056*
H5B	0.614785	0.678590	0.266612	0.056*
C6	0.5059 (3)	0.6795 (2)	0.32441 (7)	0.0378 (5)
H6A	0.627880	0.688390	0.337523	0.045*
H6B	0.448385	0.768242	0.322833	0.045*
C7	0.1215 (3)	0.6284 (2)	0.39842 (6)	0.0314 (5)
C8	0.4316 (3)	0.6997 (2)	0.41602 (6)	0.0320 (5)
C9	0.1762 (3)	0.7788 (2)	0.44935 (6)	0.0355 (5)
N1	0.3141 (2)	0.63940 (18)	0.38824 (5)	0.0297 (4)
N2	0.3644 (3)	0.7730 (2)	0.44638 (5)	0.0371 (5)
N3	0.0539 (3)	0.6996 (2)	0.42924 (6)	0.0364 (5)
N4	0.6155 (3)	0.6863 (2)	0.41318 (7)	0.0416 (5)
N5	0.1052 (4)	0.8655 (3)	0.47590 (7)	0.0531 (6)
S1	−0.02187 (9)	0.52678 (7)	0.37155 (2)	0.0437 (2)
H4C	0.687 (4)	0.731 (3)	0.4295 (7)	0.045 (7)*
H4D	0.678 (4)	0.637 (3)	0.3961 (8)	0.052 (8)*
H5C	0.185 (5)	0.915 (3)	0.4903 (10)	0.076 (10)*
H5D	−0.011 (4)	0.874 (3)	0.4776 (8)	0.046 (8)*
O1	0.6834 (3)	0.9457 (2)	0.47110 (6)	0.0525 (5)
H1O	0.582 (5)	0.905 (3)	0.4719 (9)	0.063*
H2O	0.654 (5)	0.993 (3)	0.4505 (9)	0.063*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0252 (12)	0.0335 (11)	0.0292 (10)	0.0015 (9)	0.0002 (9)	−0.0035 (8)
C2	0.0342 (13)	0.0314 (11)	0.0401 (13)	0.0003 (9)	0.0014 (10)	0.0002 (9)
C3	0.0475 (16)	0.0380 (13)	0.0544 (15)	0.0028 (12)	0.0037 (12)	−0.0124 (11)
C4	0.0534 (18)	0.0636 (18)	0.0442 (14)	0.0065 (14)	0.0130 (13)	−0.0130 (13)
C5	0.0467 (16)	0.0609 (17)	0.0334 (12)	−0.0022 (13)	0.0064 (11)	0.0032 (11)
C6	0.0360 (14)	0.0351 (12)	0.0423 (13)	0.0000 (10)	0.0045 (10)	0.0012 (10)
C7	0.0254 (12)	0.0305 (11)	0.0382 (12)	0.0011 (9)	0.0004 (9)	0.0015 (9)
C8	0.0290 (12)	0.0343 (12)	0.0327 (11)	−0.0013 (9)	−0.0012 (9)	0.0003 (9)
C9	0.0302 (13)	0.0441 (13)	0.0321 (11)	0.0000 (10)	0.0042 (9)	−0.0020 (10)
N1	0.0207 (9)	0.0341 (10)	0.0341 (9)	−0.0015 (8)	−0.0004 (7)	−0.0044 (7)
N2	0.0288 (11)	0.0491 (12)	0.0332 (10)	−0.0004 (9)	−0.0001 (8)	−0.0080 (9)
N3	0.0257 (10)	0.0453 (11)	0.0382 (10)	−0.0032 (8)	0.0042 (8)	−0.0079 (9)
N4	0.0243 (11)	0.0550 (14)	0.0455 (12)	0.0014 (10)	−0.0041 (9)	−0.0145 (10)
N5	0.0295 (14)	0.0732 (17)	0.0567 (14)	−0.0022 (12)	0.0078 (11)	−0.0297 (12)
S1	0.0250 (3)	0.0452 (4)	0.0609 (4)	−0.0053 (3)	0.0014 (3)	−0.0173 (3)
O1	0.0395 (12)	0.0657 (14)	0.0522 (11)	−0.0120 (9)	−0.0087 (9)	0.0006 (9)

Geometric parameters (Å, º) top

C1—N1	1.496 (3)	C6—H6B	0.9700
C1—C6	1.517 (3)	C7—N3	1.328 (3)
C1—C2	1.519 (3)	C7—N1	1.408 (3)
C1—H1	0.9800	C7—S1	1.683 (2)
C2—C3	1.520 (3)	C8—N4	1.312 (3)
C2—H2A	0.9700	C8—N2	1.326 (3)
C2—H2B	0.9700	C8—N1	1.375 (3)
C3—C4	1.517 (4)	C9—N5	1.327 (3)
C3—H3A	0.9700	C9—N2	1.337 (3)
C3—H3B	0.9700	C9—N3	1.344 (3)
C4—C5	1.515 (4)	N4—H4C	0.86 (3)
C4—H4A	0.9700	N4—H4D	0.87 (3)
C4—H4B	0.9700	N5—H5C	0.89 (4)
C5—C6	1.525 (3)	N5—H5D	0.83 (3)
C5—H5A	0.9700	O1—H1O	0.82 (4)
C5—H5B	0.9700	O1—H2O	0.85 (3)
C6—H6A	0.9700

N1—C1—C6	114.88 (17)	H5A—C5—H5B	107.9
N1—C1—C2	113.10 (17)	C1—C6—C5	108.28 (19)
C6—C1—C2	112.89 (18)	C1—C6—H6A	110.0
N1—C1—H1	104.9	C5—C6—H6A	110.0
C6—C1—H1	104.9	C1—C6—H6B	110.0
C2—C1—H1	104.9	C5—C6—H6B	110.0
C1—C2—C3	109.42 (19)	H6A—C6—H6B	108.4
C1—C2—H2A	109.8	N3—C7—N1	119.42 (19)
C3—C2—H2A	109.8	N3—C7—S1	120.31 (17)
C1—C2—H2B	109.8	N1—C7—S1	120.28 (16)
C3—C2—H2B	109.8	N4—C8—N2	117.7 (2)
H2A—C2—H2B	108.2	N4—C8—N1	120.5 (2)
C4—C3—C2	112.0 (2)	N2—C8—N1	121.7 (2)
C4—C3—H3A	109.2	N5—C9—N2	117.0 (2)
C2—C3—H3A	109.2	N5—C9—N3	117.4 (2)
C4—C3—H3B	109.2	N2—C9—N3	125.5 (2)
C2—C3—H3B	109.2	C8—N1—C7	117.35 (18)
H3A—C3—H3B	107.9	C8—N1—C1	123.59 (17)
C5—C4—C3	111.8 (2)	C7—N1—C1	119.05 (17)
C5—C4—H4A	109.3	C8—N2—C9	115.88 (19)
C3—C4—H4A	109.3	C7—N3—C9	117.17 (19)
C5—C4—H4B	109.3	C8—N4—H4C	119.0 (17)
C3—C4—H4B	109.3	C8—N4—H4D	127.5 (19)
H4A—C4—H4B	107.9	H4C—N4—H4D	114 (3)
C4—C5—C6	111.7 (2)	C9—N5—H5C	118 (2)
C4—C5—H5A	109.3	C9—N5—H5D	118.9 (19)
C6—C5—H5A	109.3	H5C—N5—H5D	123 (3)
C4—C5—H5B	109.3	H1O—O1—H2O	95 (3)
C6—C5—H5B	109.3

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4C···N3ⁱ	0.86 (3)	2.62 (3)	3.151 (3)	121 (2)
N4—H4C···O1	0.86 (3)	2.53 (3)	3.239 (3)	140 (2)
N4—H4D···S1ⁱ	0.87 (3)	2.52 (3)	3.313 (2)	152 (2)
N5—H5C···O1ⁱⁱ	0.89 (4)	2.09 (4)	2.967 (3)	167 (3)
N5—H5D···O1ⁱⁱⁱ	0.83 (3)	2.29 (3)	3.094 (3)	164 (3)
O1—H1O···N2	0.82 (4)	2.19 (3)	2.949 (3)	153 (3)
O1—H2O···N3^iv	0.85 (3)	2.61 (3)	3.325 (3)	142 (3)
O1—H2O···S1^iv	0.85 (3)	2.79 (3)	3.574 (2)	153 (3)

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

Acknowledgements

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

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