Crystal structures and Hirshfeld surface analyses of 2-[(4,6-di­amino­pyrimidin-2-yl)sulfan­yl]-N-(pyridin-2-yl)acetamide and 2-[(4,6-di­amino­pyrimidin-2-yl)sulfan­yl]-N-(pyrazin-2-yl)acetamide

Choudhury, M.; Viswanathan, V.; Timiri, A.K.; Sinha, B.N.; Jayaprakash, V.; Velmurugan, D.

doi:10.1107/S2056989018005704

research communications

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 74| Part 5| May 2018| Pages 718-723

https://doi.org/10.1107/S2056989018005704

Open

access

Crystal structures and Hirshfeld surface analyses of 2-[(4,6-diaminopyrimidin-2-yl)sulfanyl]-N-(pyridin-2-yl)acetamide and 2-[(4,6-diaminopyrimidin-2-yl)sulfanyl]-N-(pyrazin-2-yl)acetamide

Manisha Choudhury,^a Vijayan Viswanathan,^a Ajay Kumar Timiri,^b Barij Nayan Sinha,^b Venkatesan Jayaprakash ^b and Devadasan Velmurugan ^a ^*

^aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and ^bDepartment of Pharmaceutical Science and Technology, Birla Institute of Technology, Mesta, Ranchi 835215, Jharkhand, India
^*Correspondence e-mail: shirai2011@gmail.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 8 March 2018; accepted 11 April 2018; online 27 April 2018)

In the title compounds, C₁₁H₁₂N₆OS (I) and C₁₀H₁₁N₇OS (II), the diaminopyrimidine ring makes dihedral angles of 71.10 (9)° with the pyridine ring in (I) and 62.93 (15)° with the pyrazine ring in (II). The ethanamine group, –CH₂–C(=O)–NH– lies in the plane of the pyridine and pyrazine rings in compounds (I) and (II), respectively. In both compounds, there is an intramolecular N—H⋯N hydrogen bond forming an S(7) ring motif and a short C—H⋯O interaction forming an S(6) loop. In the crystals of both compounds, molecules are linked by pairs of N—H⋯N hydrogen bonds, forming inversion dimers with R₂²(8) ring motifs. In (I), the dimers are linked by N—H⋯O and N—H⋯N hydrogen bonds, forming layers parallel to (1 $[\overline{1}]$ $[\overline{1}]$ ). The layers are linked by offset π–π interactions [intercentroid distance = 3.777 (1) Å], forming a three-dimensional supramolecular structure. In (II), the dimers are linked by N—H⋯O, N—H⋯N and C—H⋯O hydrogen bonds, also forming a three-dimensional supramolecular structure.

Keywords: crystal structure; 4,6-diaminopyrimidine; sulfanyl; acetamide; pyridine; pyrazine; hydrogen bonding; offset π-π interactions; Hirshfeld surface.

CCDC references: 1836419; 1836418

1. Chemical context

An important property of diaminopyrimidine derivatives is their inhibition potential against cancer targets. Because of the limited capacity of drugs that can cure cancer, there is always an urgent requirement for new chemotherapeutics. 2,4-Diaminopyrimidine derivatives combined with arylthiazole derivatives have shown to possess significant anti-proliferation properties against breast cancer cell lines (Zhou et al., 2015 ). 2,4-Diaminopyrimidine derivatives have shown significant inhibitory activity against influenza viruses (Kimura et al., 2006 ). A series of 2,4- diaminopyrimidine derivatives were evaluated against Bacillus anthracis, which showed inhibition (Nammalwar et al., 2012 ). Dihydrofolate reductase inhibitor drugs such as pyrimethamine, trimetrexate and piritrexim (Nelson & Rosowsky, 2001 ) and the antibiotics iclaprim and trimethoprim all include diaminopyrimidine as the fundamental structural motif. Diaminopyrimidine derivatives have also shown anti-retroviral activity (Hocková et al., 2004 $[Hocková, D., Holý, A. N., Masoj\?ídková, M., Andrei, G., Snoeck, R., De Clercq, E. & Balzarini, J. (2004). Bioorg. Med. Chem. 12, 3197-3202.]$ ), antibacterial (Kandeel et al., 1994 ) and potential anti-microbial properties (Holla et al., 2006 ). As part of our own studies in this area, we report herein on the syntheses, crystal structures and Hirshfeld surface analyses of the title compounds, 2-[(4,6-diaminopyrimidin-2-yl)sulfanyl]-N-(pyridin-2-yl)acetamide (I) and 2-[(4,6-diaminopyrimidin-2-yl)sulfanyl]-N-(pyrazin-2-yl)acetamide (II).

2. Structural commentary

The molecular structure of compounds (I) and (II) are shown in the Figs. 1 and 2, respectively. Compound (I) crystallizes in the triclinic space group P $[\overline{1}]$ and compound (II) crystallizes in the monoclinic space group P2₁/c. In both the compounds, there is an intramolecular N—H⋯N hydrogen bond forming an S(7) ring motif and a short C—H⋯O interaction forming an S(6) loop; see Tables 1 and 2 for details of the hydrogen bonding. The nitrogen atoms N1 and N2 lie in the plane of the pyrimidine ring to which they are attached [deviations are −0.0269 (17) and 0.0521 (16) Å, respectively, for compound (I), and 0.0350 (28) and 0.0284 (28) Å, respectively, for compound (II)]. The diaminopyrimidine ring makes a dihedral angle of 71.10 (9)° with the pyridine ring in compound (I) and a dihedral angle of 62.93 (15)° with the pyrazine ring in compound (II). In (I) the ethanamine group (N5/O1/C6/C5) and the pyridine ring are coplanar, as evidenced by torsion angle C7—N5—C6—C5 = 179.1 (2)°. In (II) the ethanamine group (N5/O1/C6/C5) and pyrazine ring also lie in a plane [C7—N5—C6—C5 = 177.6 (3)°]. Bond lengths C4—S1 [1.768 (2) Å] and C5—S1 [1.802 (2) Å] for compound (I), and C4—S1 [1.768 (3) Å] and C5—S1 [1.795 (3) Å] for compound (II), are comparable with values reported for similar compounds (see Section 4. Database survey).

Table 1
Hydrogen-bond geometry (Å, °) for (I)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5⋯N3	0.86 (2)	2.18 (2)	2.975 (2)	154 (2)
C8—H8⋯O1	0.93	2.31	2.894 (2)	121
N2—H2B⋯N4ⁱ	0.88 (2)	2.20 (2)	3.082 (2)	178 (2)
N1—H1A⋯N6ⁱⁱ	0.86 (2)	2.38 (2)	3.174 (2)	155 (2)
N2—H2A⋯O1ⁱⁱⁱ	0.86 (2)	2.13 (2)	2.956 (2)	159 (2)
Symmetry codes: (i) -x+2, -y+1, -z+2; (ii) -x+1, -y+1, -z+1; (iii) x+1, y+1, z.

Table 2
Hydrogen-bond geometry (Å, °) for (II)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5⋯N3	0.82 (3)	2.25 (3)	2.993 (4)	151 (3)
C8—H8⋯O1	0.93	2.24	2.854 (4)	123
N2—H2B⋯N4ⁱ	1.00 (3)	2.11 (3)	3.092 (4)	169 (3)
N1—H1A⋯O1ⁱⁱ	0.86 (3)	2.06 (4)	2.904 (4)	167 (3)
N2—H2A⋯N7ⁱⁱⁱ	0.85 (3)	2.41 (3)	3.235 (4)	164 (3)
C9—H9⋯O1^iv	0.93	2.56	3.368 (4)	145
Symmetry codes: (i) -x+1, -y, -z+1; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) x-1, y, z; (iv) $[-x+{\script{5\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Figure 1
The molecular structure of the compound (I)

, showing the atom labelling and displacement ellipsoids drawn at the 50% probability level. The intramolecular N—H⋯N and C—H⋯O hydrogen bonds (see Table 1

) are shown as dashed lines.

Figure 2
The molecular structure of the compound (II)

, showing the atom labelling and displacement ellipsoids drawn at the 50% probability level. The intramolecular N—H⋯N and C—H⋯O hydrogen bonds (see Table 2

) are shown as dashed lines.

3. Supramolecular features

The crystal packing in compound (I) is illustrated in Fig. 3, and that for compound (II) in Fig. 4. Details of the hydrogen-bonding geometry in compound (I) are given in Table 1 and in Table 2 for (II). In the crystals of both compounds, molecules are linked by pairs of N2—H2B⋯N4ⁱ hydrogen bonds, forming inversion dimers with R₂²(8) ring motifs (Figs. 3 and 4, respectively).

Figure 3
A view normal to the (1 $[\overline{1}]$ $[\overline{1}]$ ) plane of the crystal packing of compound (I)

. The hydrogen bonds (see Table 1

) are shown as dashed lines and C-bound H atoms have been omitted for clarity.

Figure 4
A view along the a axis of the crystal packing of compound (II)

. The hydrogen bonds (see Table 2

) are shown as dashed lines, and C-bound H atoms have been omitted for clarity.

In the crystal of (I), the dimers are linked by N2—H2A⋯O1ⁱⁱⁱ hydrogen bonds, forming ribbons along [010], enclosing R₄⁴(18) ring motifs. Adjacent ribbons are linked by N1—H1A⋯N6ⁱⁱ hydrogen bonds, forming sheets lying parallel to the (1 $[\overline{1}]$ $[\overline{1}]$ ) plane, see Fig. 3. The layers are linked by offset π–π interactions, forming a three-dimensional supramolecular structure [Cg⋯Cg^v = 3.777 (1) Å, interplanar distance = 3.483 (1) Å, slippage = 1.459 Å, Cg is the centroid of the pyridine ring (N6/C7–C11); symmetry code: (v) −x + 1, −y, −z + 1)].

In the crystal of (II), the dimers are linked by N1—H1A⋯Oⁱⁱ, N2—H2A⋯N7ⁱⁱⁱ and C9—H9⋯O1^iv hydrogen bonds (Table 2), forming a three-dimensional supramolecular structure (Fig. 4). In contrast, in the crystal of (II) there are no π–π interactions present.

4. Database survey

A search of the Cambridge Structure Database (Version 5.39, last update February 2018; Groom et al., 2016 ) for [(4,6-diaminopyrmidin-2-yl)sulfanyl]acetamide yielded nine hits, eight of which have a substituted phenyl substituent in place of the pyridine ring in (I) and the pyrazine ring in (II), and one a naphthalene group (JARPOK; Subasri et al., 2017a ). They include the following analogues: 3-nitrophenyl (ARAROC; Subasri et al., 2016 ), 2-chlorophenyl (ARARUI; Subasri et al., 2016), 2-methylphenyl (GOKWIO; Subasri et al., 2014 ), 4-fluorophenyl (JARPUQ; Subasri et al., 2017a), 2,4-dimethylphenyl (JAXFIA; Choudhury et al., 2017 ), 3-methoxyphenyl (JAXFOG; Choudhury et al., 2017), 4-chlorophenyl (KAPQIE; Subasri et al., 2017b ), and 3-chlorophenyl (KAPQOK; Subasri et al., 2017b).

In these eight compounds, the diaminopyrimidine and benzene rings are inclined to one another by dihedral angles varying from ca 42.25 to 78.33°. The dihedral angle between the diaminopyrimidine and the pyridine ring in (I) is 71.10 (9)° and with the pyrazine ring in (II) is 62.93 (15)°, well within these limits. As in the title compounds, there is also an intramolecular N—H⋯N hydrogen bond present in all eight compounds, stabilizing the folded conformation of each molecule. In the crystals of all but two compounds (ARAROC and JARPUQ), molecules are linked by pairs of N—H⋯N hydrogen bonds, involving the 4,6-diaminopyrimidine moieties, forming inversion dimers with R₂²(8) ring motifs, as for compounds (I) and (II).

5. Hirshfeld surface analysis

In Figs. 5 and 6, the ball and stick model of the front and back views of the compounds (I) and (II), respectively, and the intermolecular contacts are shown by conventional mapping of d_norm on the molecular Hirshfeld surfaces, where the red-spot areas denote intermolecular contacts involved in the hydrogen-bonding interactions (McKinnon et al., 2007 ). The electrostatic potential is mapped on the Hirshfeld surface using the STO-3G basis set at the Hartree–Fock theory over the range of ±0.025 a.u. The positive electrostatic potential (blue region) over the surface shows hydrogen-donor potential, and the hydrogen-bond acceptors are shown by negative electrostatic potential (red regions); see Figs. 5 and 6. The two-dimensional fingerprint plots [Fig. 7 for (I) and Fig. 8 for (II)] are deconvoluted to highlight atom-pair close contacts by which different atomic types, overlapping the full fingerprint can be separated based on different interaction types. For compound (I), intermolecular H⋯H contacts of 39.1% are the most significant, followed by 17.7% for N⋯H/H⋯N, 12% for C⋯H/H⋯C, 9.3% for O⋯H/H⋯O, 8.4% for S⋯H/H⋯S and 4.1% for C⋯C contacts. In contrast, for compound (II) the H⋯H contacts at 28.2% are significantly lower than in (I), while the N⋯H/H⋯N contacts at 27% are significantly higher than in (I). The C⋯C contacts at only 1.9% are much lower than in (I) where offset π–π interactions are observed in the crystal structure.

Figure 5
Ball and stick, Hirshfeld surface and electrostatic potential surface diagrams for compound (I)

Figure 6
Ball and stick, Hirshfeld surface and electrostatic potential surface diagrams for compound (II)

Figure 7
The 2D fingerprint plot for all the intermolecular contacts for compound (I)

Figure 8
The 2D fingerprint plot for all the intermolecular contacts for compound (II)

6. Synthesis and crystallization

Compound (I): To a solution of 4, 6-diamino-pyrimidine-2-thiol (0.5 g; 3.52 mmol) in 25 ml of ethanol, (0.2g; 3.52 mmol) potassium hydroxide was added and refluxed for about 30 min. Then an equimolar quantity of 2-chloro-N-(pyridin-2-yl)acetamide (3.52 mmol) was added to the above reaction mixture and it was refluxed for 5 h. Evaporation of the organic layer under vacuum provided compound (I). After purification, the compound was crystallized from ethanol solution by slow evaporation of the solvent giving yellow block-like crystals.

Compound (II): To a solution of 4, 6-diamino-pyrimidine-2-thiol (0.5 g; 3.52 mmol) in 25 ml of ethanol, (0.2g; 3.52 mmol) potassium hydroxide was added and refluxed for about 30 min. Then an equimolar quantity of 2-chloro-N-(pyrazin-2-yl)acetamide (3.52 mmol) was added to the above reaction mixture and it was refluxed for 5.5 h. Evaporation of the organic layer under vacuum resulted in compound (II). After purification, the compound was crystallized from ethanol solution by slow evaporation of the solvent giving yellow block-like crystals.

7. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. For both compounds, the NH₂ and NH H atoms were located in difference-Fourier maps and freely refined, and the C-bound H atoms were placed in calculated positions and refined in the riding model: C—H = 0.93–0.97 Å with U_iso(H) = 1.2U_eq(C).

Table 3
Experimental details

	(I)	(II)
Crystal data
Chemical formula	C₁₁H₁₂N₆OS	C₁₀H₁₁N₇OS
M_r	276.33	277.32
Crystal system, space group	Triclinic, P $[\overline{1}]$	Monoclinic, P2₁/n
Temperature (K)	293	293
a, b, c (Å)	7.2341 (2), 9.3852 (2), 9.7971 (2)	12.1333 (5), 8.1561 (3), 12.8442 (5)
α, β, γ (°)	95.820 (1), 91.116 (1), 105.682 (1)	90, 94.307 (3), 90
V (Å³)	636.33 (3)	1267.48 (9)
Z	2	4
Radiation type	Mo Kα	Mo Kα
μ (mm⁻¹)	0.26	0.26
Crystal size (mm)	0.30 × 0.25 × 0.20	0.28 × 0.25 × 0.20

Data collection
Diffractometer	Bruker SMART APEXII area-detector	Bruker SMART APEXII area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2008 )	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.742, 0.841	0.723, 0.863
No. of measured, independent and observed [I > 2σ(I)] reflections	9447, 2605, 2160	11968, 3124, 1320
R_int	0.020	0.084
(sin θ/λ)_max (Å⁻¹)	0.626	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.094, 1.05	0.054, 0.126, 0.94
No. of reflections	2605	3124
No. of parameters	192	192
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.20	0.20, −0.23
Computer programs: APEX2 and SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008 ), SHELXL2016 (Sheldrick, 2015 ), PLATON (Spek, 2009 ) and Mercury (Macrae et al., 2008 ).

Supporting information

CCDC references: 1836419; 1836418

Crystal structure: contains datablocks global, I, II. DOI: https://doi.org/10.1107/S2056989018005704/su5430sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989018005704/su5430Isup4.hkl

Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S2056989018005704/su5430IIsup5.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989018005704/su5430Isup4.cml

Supporting information file. DOI: https://doi.org/10.1107/S2056989018005704/su5430IIsup5.cml

checkCIF report

Computing details top

For both structures, data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2016 (Sheldrick, 2015) and PLATON (Spek, 2009).

2-[(4,6-Diaminopyrimidin-2-yl)sulfanyl]-N-(pyridin-2-yl)acetamide (I) top

Crystal data top

C₁₁H₁₂N₆OS	Z = 2
M_r = 276.33	F(000) = 288
Triclinic, P1	D_x = 1.442 Mg m⁻³
a = 7.2341 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.3852 (2) Å	Cell parameters from 2605 reflections
c = 9.7971 (2) Å	θ = 2.1–26.4°
α = 95.820 (1)°	µ = 0.26 mm⁻¹
β = 91.116 (1)°	T = 293 K
γ = 105.682 (1)°	Block, yellow
V = 636.33 (3) Å³	0.30 × 0.25 × 0.20 mm

Data collection top

Bruker SMART APEXII area-detector diffractometer	2160 reflections with I > 2σ(I)
Radiation source: X-ray	R_int = 0.020
ω and φ scans	θ_max = 26.4°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −9→9
T_min = 0.742, T_max = 0.841	k = −11→11
9447 measured reflections	l = −10→12
2605 independent reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.034	Hydrogen site location: mixed
wR(F²) = 0.094	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0443P)² + 0.1669P] where P = (F_o² + 2F_c²)/3
2605 reflections	(Δ/σ)_max < 0.001
192 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.20 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
S1	0.47564 (6)	0.24187 (5)	0.97878 (4)	0.04443 (15)
O1	0.1201 (2)	−0.07191 (14)	0.81504 (14)	0.0637 (4)
N1	0.4212 (3)	0.58093 (19)	0.63223 (17)	0.0509 (4)
H1A	0.470 (3)	0.652 (2)	0.584 (2)	0.059 (6)*
H1B	0.299 (3)	0.546 (2)	0.641 (2)	0.066 (7)*
N2	1.0373 (2)	0.60541 (19)	0.83751 (19)	0.0500 (4)
H2A	1.087 (3)	0.696 (2)	0.820 (2)	0.059 (6)*
H2B	1.092 (3)	0.590 (2)	0.914 (2)	0.071 (7)*
N3	0.45530 (19)	0.42030 (14)	0.78589 (14)	0.0378 (3)
N4	0.75997 (18)	0.44133 (14)	0.89781 (13)	0.0374 (3)
N5	0.2555 (2)	0.10689 (16)	0.67916 (14)	0.0395 (3)
H5	0.304 (3)	0.201 (2)	0.6830 (18)	0.046 (5)*
N6	0.3287 (2)	0.11118 (16)	0.45436 (15)	0.0458 (4)
C1	0.5404 (2)	0.53494 (17)	0.71413 (16)	0.0373 (4)
C2	0.7366 (2)	0.59919 (18)	0.72509 (17)	0.0398 (4)
H2	0.795008	0.672763	0.670694	0.048*
C3	0.8435 (2)	0.55043 (16)	0.81970 (16)	0.0367 (4)
C4	0.5717 (2)	0.38421 (16)	0.87394 (15)	0.0351 (4)
C5	0.2265 (2)	0.17793 (19)	0.91965 (17)	0.0452 (4)
H5A	0.149123	0.139634	0.994486	0.054*
H5B	0.185101	0.261192	0.891905	0.054*
C6	0.1943 (2)	0.05740 (18)	0.80001 (18)	0.0415 (4)
C7	0.2500 (2)	0.02603 (17)	0.55029 (17)	0.0369 (4)
C8	0.1697 (3)	−0.12615 (19)	0.5237 (2)	0.0506 (4)
H8	0.118824	−0.182978	0.593511	0.061*
C9	0.1674 (3)	−0.1909 (2)	0.3911 (2)	0.0603 (5)
H9	0.113148	−0.292746	0.369861	0.072*
C10	0.2447 (3)	−0.1056 (2)	0.2905 (2)	0.0574 (5)
H10	0.243138	−0.147400	0.200125	0.069*
C11	0.3246 (3)	0.0435 (2)	0.32694 (19)	0.0551 (5)
H11	0.379420	0.101358	0.258857	0.066*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0510 (3)	0.0393 (2)	0.0344 (2)	−0.00414 (19)	0.00358 (18)	0.00918 (17)
O1	0.0848 (10)	0.0348 (7)	0.0585 (8)	−0.0084 (6)	0.0102 (7)	0.0109 (6)
N1	0.0466 (10)	0.0522 (10)	0.0532 (10)	0.0079 (8)	−0.0012 (8)	0.0183 (8)
N2	0.0377 (8)	0.0444 (9)	0.0648 (11)	0.0003 (7)	0.0006 (7)	0.0222 (8)
N3	0.0399 (7)	0.0308 (7)	0.0382 (7)	0.0019 (6)	0.0022 (6)	0.0041 (5)
N4	0.0404 (8)	0.0310 (7)	0.0369 (7)	0.0020 (6)	0.0018 (6)	0.0064 (5)
N5	0.0438 (8)	0.0288 (7)	0.0397 (8)	−0.0008 (6)	0.0032 (6)	0.0044 (6)
N6	0.0523 (9)	0.0425 (8)	0.0418 (8)	0.0106 (7)	0.0039 (7)	0.0070 (6)
C1	0.0443 (9)	0.0331 (8)	0.0332 (8)	0.0084 (7)	0.0034 (7)	0.0030 (6)
C2	0.0427 (9)	0.0349 (8)	0.0411 (9)	0.0058 (7)	0.0085 (7)	0.0127 (7)
C3	0.0395 (9)	0.0281 (8)	0.0397 (9)	0.0042 (6)	0.0063 (7)	0.0040 (6)
C4	0.0427 (9)	0.0266 (7)	0.0311 (8)	0.0022 (6)	0.0056 (7)	−0.0004 (6)
C5	0.0451 (10)	0.0417 (9)	0.0412 (9)	−0.0018 (7)	0.0134 (8)	0.0050 (7)
C6	0.0385 (9)	0.0354 (9)	0.0458 (10)	0.0003 (7)	0.0037 (7)	0.0087 (7)
C7	0.0319 (8)	0.0358 (8)	0.0419 (9)	0.0079 (6)	−0.0010 (7)	0.0038 (7)
C8	0.0531 (11)	0.0375 (9)	0.0546 (11)	0.0026 (8)	0.0031 (9)	0.0009 (8)
C9	0.0629 (13)	0.0441 (11)	0.0672 (13)	0.0099 (9)	−0.0011 (10)	−0.0111 (9)
C10	0.0611 (12)	0.0643 (13)	0.0488 (11)	0.0266 (10)	−0.0007 (9)	−0.0100 (10)
C11	0.0636 (12)	0.0607 (12)	0.0436 (10)	0.0204 (10)	0.0081 (9)	0.0073 (9)

Geometric parameters (Å, º) top

S1—C4	1.7682 (15)	N6—C7	1.332 (2)
S1—C5	1.8021 (18)	N6—C11	1.338 (2)
O1—C6	1.2124 (19)	C1—C2	1.381 (2)
N1—C1	1.348 (2)	C2—C3	1.384 (2)
N1—H1A	0.86 (2)	C2—H2	0.9300
N1—H1B	0.86 (2)	C5—C6	1.512 (2)
N2—C3	1.358 (2)	C5—H5A	0.9700
N2—H2A	0.86 (2)	C5—H5B	0.9700
N2—H2B	0.88 (2)	C7—C8	1.384 (2)
N3—C4	1.324 (2)	C8—C9	1.376 (3)
N3—C1	1.358 (2)	C8—H8	0.9300
N4—C4	1.328 (2)	C9—C10	1.365 (3)
N4—C3	1.3570 (19)	C9—H9	0.9300
N5—C6	1.354 (2)	C10—C11	1.368 (3)
N5—C7	1.400 (2)	C10—H10	0.9300
N5—H5	0.856 (19)	C11—H11	0.9300

C4—S1—C5	102.83 (8)	C6—C5—S1	111.72 (12)
C1—N1—H1A	118.3 (14)	C6—C5—H5A	109.3
C1—N1—H1B	117.3 (15)	S1—C5—H5A	109.3
H1A—N1—H1B	124 (2)	C6—C5—H5B	109.3
C3—N2—H2A	117.2 (13)	S1—C5—H5B	109.3
C3—N2—H2B	117.6 (15)	H5A—C5—H5B	107.9
H2A—N2—H2B	110 (2)	O1—C6—N5	124.47 (16)
C4—N3—C1	114.94 (13)	O1—C6—C5	121.07 (15)
C4—N4—C3	115.04 (13)	N5—C6—C5	114.46 (14)
C6—N5—C7	129.23 (14)	N6—C7—C8	123.05 (16)
C6—N5—H5	114.6 (12)	N6—C7—N5	112.92 (13)
C7—N5—H5	116.2 (12)	C8—C7—N5	124.02 (15)
C7—N6—C11	116.91 (15)	C9—C8—C7	118.03 (18)
N1—C1—N3	115.65 (15)	C9—C8—H8	121.0
N1—C1—C2	122.72 (15)	C7—C8—H8	121.0
N3—C1—C2	121.63 (15)	C10—C9—C8	120.00 (18)
C1—C2—C3	117.79 (14)	C10—C9—H9	120.0
C1—C2—H2	121.1	C8—C9—H9	120.0
C3—C2—H2	121.1	C9—C10—C11	117.86 (18)
N4—C3—N2	116.08 (15)	C9—C10—H10	121.1
N4—C3—C2	121.51 (14)	C11—C10—H10	121.1
N2—C3—C2	122.39 (15)	N6—C11—C10	124.13 (18)
N3—C4—N4	128.88 (14)	N6—C11—H11	117.9
N3—C4—S1	119.16 (12)	C10—C11—H11	117.9
N4—C4—S1	111.95 (12)

C4—N3—C1—N1	−174.86 (14)	C7—N5—C6—O1	−0.5 (3)
C4—N3—C1—C2	5.2 (2)	C7—N5—C6—C5	179.12 (15)
N1—C1—C2—C3	175.39 (15)	S1—C5—C6—O1	105.06 (17)
N3—C1—C2—C3	−4.7 (2)	S1—C5—C6—N5	−74.58 (17)
C4—N4—C3—N2	−176.87 (14)	C11—N6—C7—C8	1.2 (2)
C4—N4—C3—C2	1.5 (2)	C11—N6—C7—N5	−178.11 (15)
C1—C2—C3—N4	1.2 (2)	C6—N5—C7—N6	−178.11 (16)
C1—C2—C3—N2	179.38 (15)	C6—N5—C7—C8	2.5 (3)
C1—N3—C4—N4	−2.5 (2)	N6—C7—C8—C9	−1.7 (3)
C1—N3—C4—S1	177.30 (10)	N5—C7—C8—C9	177.57 (17)
C3—N4—C4—N3	−0.8 (2)	C7—C8—C9—C10	0.7 (3)
C3—N4—C4—S1	179.39 (10)	C8—C9—C10—C11	0.7 (3)
C5—S1—C4—N3	3.32 (14)	C7—N6—C11—C10	0.2 (3)
C5—S1—C4—N4	−176.85 (11)	C9—C10—C11—N6	−1.2 (3)
C4—S1—C5—C6	87.65 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5···N3	0.86 (2)	2.18 (2)	2.975 (2)	154 (2)
C8—H8···O1	0.93	2.31	2.894 (2)	121
N2—H2B···N4ⁱ	0.88 (2)	2.20 (2)	3.082 (2)	178 (2)
N1—H1A···N6ⁱⁱ	0.86 (2)	2.38 (2)	3.174 (2)	155 (2)
N2—H2A···O1ⁱⁱⁱ	0.86 (2)	2.13 (2)	2.956 (2)	159 (2)

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

2-[(4,6-Diaminopyrimidin-2-yl)sulfanyl]-N-(pyrazin-2-yl)acetamide (II) top

Crystal data top

C₁₀H₁₁N₇OS	F(000) = 576
M_r = 277.32	D_x = 1.453 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 12.1333 (5) Å	Cell parameters from 3124 reflections
b = 8.1561 (3) Å	θ = 2.2–28.3°
c = 12.8442 (5) Å	µ = 0.26 mm⁻¹
β = 94.307 (3)°	T = 293 K
V = 1267.48 (9) Å³	Block, yellow
Z = 4	0.28 × 0.25 × 0.20 mm

Data collection top

Bruker SMART APEXII area-detector diffractometer	1320 reflections with I > 2σ(I)
Radiation source: X-ray	R_int = 0.084
ω and φ scans	θ_max = 28.3°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −16→12
T_min = 0.723, T_max = 0.863	k = −10→9
11968 measured reflections	l = −17→17
3124 independent reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.054	Hydrogen site location: mixed
wR(F²) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 0.94	w = 1/[σ²(F_o²) + (0.0452P)²] where P = (F_o² + 2F_c²)/3
3124 reflections	(Δ/σ)_max = 0.001
192 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Special details top

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

	x	y	z	U_iso*/U_eq
S1	0.77107 (6)	0.20394 (11)	0.50448 (6)	0.0525 (3)
O1	1.06221 (18)	0.2503 (3)	0.55054 (17)	0.0779 (8)
N1	0.6951 (3)	0.2961 (4)	0.8740 (2)	0.0651 (9)
H1A	0.651 (3)	0.297 (4)	0.923 (3)	0.084 (13)*
H1B	0.760 (3)	0.342 (4)	0.881 (3)	0.079 (13)*
N2	0.4369 (2)	0.0046 (4)	0.6423 (3)	0.0635 (9)
H2A	0.391 (2)	−0.015 (4)	0.687 (2)	0.060 (11)*
H2B	0.423 (2)	−0.044 (4)	0.571 (3)	0.080 (11)*
N3	0.72886 (19)	0.2473 (3)	0.70403 (17)	0.0452 (7)
N4	0.59901 (19)	0.1011 (3)	0.58901 (17)	0.0463 (7)
N5	0.9712 (2)	0.1889 (3)	0.69294 (19)	0.0494 (7)
H5	0.912 (2)	0.197 (4)	0.719 (2)	0.057 (11)*
N6	1.0164 (2)	0.0445 (3)	0.84291 (19)	0.0545 (7)
N7	1.2266 (2)	−0.0273 (4)	0.7815 (2)	0.0659 (8)
C1	0.6580 (3)	0.2321 (4)	0.7813 (2)	0.0450 (8)
C2	0.5579 (2)	0.1540 (4)	0.7649 (2)	0.0466 (8)
H2	0.509877	0.146453	0.817830	0.056*
C3	0.5306 (2)	0.0872 (4)	0.6680 (2)	0.0438 (8)
C4	0.6909 (2)	0.1845 (4)	0.6132 (2)	0.0421 (7)
C5	0.8779 (2)	0.3427 (4)	0.5525 (2)	0.0497 (9)
H5A	0.897729	0.412594	0.495784	0.060*
H5B	0.849528	0.412281	0.605640	0.060*
C6	0.9796 (3)	0.2561 (4)	0.5981 (2)	0.0499 (9)
C7	1.0498 (2)	0.0968 (4)	0.7528 (2)	0.0440 (8)
C8	1.1544 (3)	0.0605 (4)	0.7222 (3)	0.0613 (10)
H8	1.174535	0.098921	0.658172	0.074*
C9	1.1922 (3)	−0.0808 (4)	0.8710 (3)	0.0610 (10)
H9	1.239366	−0.144894	0.914481	0.073*
C10	1.0895 (3)	−0.0446 (4)	0.9011 (2)	0.0598 (9)
H10	1.069630	−0.083866	0.965011	0.072*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0478 (5)	0.0731 (6)	0.0376 (4)	−0.0116 (5)	0.0092 (3)	−0.0006 (4)
O1	0.0459 (15)	0.134 (3)	0.0572 (14)	0.0005 (14)	0.0236 (12)	0.0208 (14)
N1	0.062 (2)	0.091 (2)	0.0445 (17)	−0.021 (2)	0.0163 (16)	−0.0161 (17)
N2	0.0446 (19)	0.090 (3)	0.0569 (19)	−0.0240 (17)	0.0124 (16)	−0.0020 (18)
N3	0.0437 (16)	0.0552 (19)	0.0379 (13)	−0.0049 (12)	0.0104 (12)	−0.0024 (12)
N4	0.0372 (15)	0.0617 (18)	0.0408 (14)	−0.0088 (14)	0.0095 (12)	−0.0002 (13)
N5	0.0379 (18)	0.069 (2)	0.0428 (15)	−0.0018 (16)	0.0162 (13)	0.0043 (14)
N6	0.0478 (17)	0.072 (2)	0.0447 (15)	0.0030 (15)	0.0119 (13)	0.0055 (14)
N7	0.0512 (19)	0.079 (2)	0.0690 (19)	0.0126 (17)	0.0169 (15)	0.0064 (17)
C1	0.049 (2)	0.046 (2)	0.0402 (16)	0.0041 (16)	0.0087 (15)	−0.0021 (15)
C2	0.042 (2)	0.058 (2)	0.0416 (17)	−0.0005 (17)	0.0110 (14)	0.0027 (15)
C3	0.0338 (19)	0.049 (2)	0.0493 (18)	0.0015 (16)	0.0076 (15)	0.0061 (16)
C4	0.0395 (19)	0.047 (2)	0.0410 (16)	0.0036 (16)	0.0083 (14)	0.0024 (15)
C5	0.047 (2)	0.055 (2)	0.0479 (18)	−0.0136 (16)	0.0103 (15)	0.0067 (15)
C6	0.044 (2)	0.061 (2)	0.0449 (18)	−0.0142 (17)	0.0067 (16)	0.0004 (16)
C7	0.0338 (19)	0.053 (2)	0.0463 (18)	−0.0016 (16)	0.0105 (15)	−0.0048 (16)
C8	0.053 (2)	0.076 (3)	0.057 (2)	0.007 (2)	0.0187 (18)	0.0088 (19)
C9	0.054 (2)	0.073 (3)	0.057 (2)	0.012 (2)	0.0051 (17)	0.0020 (19)
C10	0.061 (3)	0.069 (3)	0.0508 (19)	0.002 (2)	0.0107 (18)	0.0063 (19)

Geometric parameters (Å, º) top

S1—C4	1.768 (3)	N6—C7	1.325 (3)
S1—C5	1.795 (3)	N6—C10	1.331 (4)
O1—C6	1.213 (3)	N7—C8	1.326 (4)
N1—C1	1.346 (4)	N7—C9	1.326 (4)
N1—H1A	0.86 (3)	C1—C2	1.374 (4)
N1—H1B	0.88 (3)	C2—C3	1.375 (4)
N2—C3	1.341 (4)	C2—H2	0.9300
N2—H2A	0.85 (3)	C5—C6	1.502 (4)
N2—H2B	1.00 (3)	C5—H5A	0.9700
N3—C4	1.325 (3)	C5—H5B	0.9700
N3—C1	1.367 (3)	C7—C8	1.389 (4)
N4—C4	1.323 (3)	C8—H8	0.9300
N4—C3	1.364 (3)	C9—C10	1.364 (4)
N5—C6	1.347 (4)	C9—H9	0.9300
N5—C7	1.398 (4)	C10—H10	0.9300
N5—H5	0.82 (3)

C4—S1—C5	102.17 (14)	N4—C4—S1	111.4 (2)
C1—N1—H1A	118 (2)	N3—C4—S1	119.0 (2)
C1—N1—H1B	120 (2)	C6—C5—S1	112.8 (2)
H1A—N1—H1B	122 (3)	C6—C5—H5A	109.0
C3—N2—H2A	121 (2)	S1—C5—H5A	109.0
C3—N2—H2B	120.4 (17)	C6—C5—H5B	109.0
H2A—N2—H2B	118 (3)	S1—C5—H5B	109.0
C4—N3—C1	114.1 (2)	H5A—C5—H5B	107.8
C4—N4—C3	114.7 (3)	O1—C6—N5	124.1 (3)
C6—N5—C7	128.4 (3)	O1—C6—C5	120.5 (3)
C6—N5—H5	118 (2)	N5—C6—C5	115.4 (3)
C7—N5—H5	114 (2)	N6—C7—C8	121.7 (3)
C7—N6—C10	115.5 (3)	N6—C7—N5	114.4 (3)
C8—N7—C9	116.0 (3)	C8—C7—N5	124.0 (3)
N1—C1—N3	114.9 (3)	N7—C8—C7	122.1 (3)
N1—C1—C2	123.3 (3)	N7—C8—H8	119.0
N3—C1—C2	121.9 (3)	C7—C8—H8	119.0
C1—C2—C3	118.2 (3)	N7—C9—C10	121.9 (3)
C1—C2—H2	120.9	N7—C9—H9	119.1
C3—C2—H2	120.9	C10—C9—H9	119.1
N2—C3—N4	114.2 (3)	N6—C10—C9	122.9 (3)
N2—C3—C2	124.3 (3)	N6—C10—H10	118.5
N4—C3—C2	121.4 (3)	C9—C10—H10	118.5
N4—C4—N3	129.6 (3)

C4—N3—C1—N1	−179.7 (3)	C7—N5—C6—O1	−2.8 (5)
C4—N3—C1—C2	1.7 (4)	C7—N5—C6—C5	177.6 (3)
N1—C1—C2—C3	−177.3 (3)	S1—C5—C6—O1	105.2 (3)
N3—C1—C2—C3	1.3 (5)	S1—C5—C6—N5	−75.2 (3)
C4—N4—C3—N2	179.0 (3)	C10—N6—C7—C8	−0.1 (5)
C4—N4—C3—C2	−0.9 (4)	C10—N6—C7—N5	179.5 (3)
C1—C2—C3—N2	178.4 (3)	C6—N5—C7—N6	−178.8 (3)
C1—C2—C3—N4	−1.7 (5)	C6—N5—C7—C8	0.8 (5)
C3—N4—C4—N3	4.6 (5)	C9—N7—C8—C7	1.1 (5)
C3—N4—C4—S1	−177.3 (2)	N6—C7—C8—N7	−0.4 (5)
C1—N3—C4—N4	−5.0 (5)	N5—C7—C8—N7	180.0 (3)
C1—N3—C4—S1	177.1 (2)	C8—N7—C9—C10	−1.3 (5)
C5—S1—C4—N4	172.4 (2)	C7—N6—C10—C9	−0.1 (5)
C5—S1—C4—N3	−9.3 (3)	N7—C9—C10—N6	0.9 (5)
C4—S1—C5—C6	93.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5···N3	0.82 (3)	2.25 (3)	2.993 (4)	151 (3)
C8—H8···O1	0.93	2.24	2.854 (4)	123
N2—H2B···N4ⁱ	1.00 (3)	2.11 (3)	3.092 (4)	169 (3)
N1—H1A···O1ⁱⁱ	0.86 (3)	2.06 (4)	2.904 (4)	167 (3)
N2—H2A···N7ⁱⁱⁱ	0.85 (3)	2.41 (3)	3.235 (4)	164 (3)
C9—H9···O1^iv	0.93	2.56	3.368 (4)	145

Symmetry codes: (i) −x+1, −y, −z+1; (ii) x−1/2, −y+1/2, z+1/2; (iii) x−1, y, z; (iv) −x+5/2, y−1/2, −z+3/2.

Acknowledgements

The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection

Funding information

MC thanks the CSIR, Government of India, for the SRF fellowship.

References

Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Choudhury, M., Viswanathan, V., Timiri, A. K., Sinha, B. N., Jayaprakash, V. & Velmurugan, D. (2017). Acta Cryst. E73, 996–1000. CrossRef IUCr Journals Google Scholar
Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. Web of Science CSD CrossRef IUCr Journals Google Scholar
Hocková, D., Holý, A. N., Masoj\?ídková, M., Andrei, G., Snoeck, R., De Clercq, E. & Balzarini, J. (2004). Bioorg. Med. Chem. 12, 3197–3202. Google Scholar
Holla, B. S., Mahalinga, M., Karthikeyan, M. S., Akberali, P. M. & Shetty, N. S. (2006). Bioorg. Med. Chem. 14, 2040–2047. Web of Science CrossRef PubMed CAS Google Scholar
Kandeel, M., El-Meligie, S., Omar, R., Roshdy, S. & Youssef, K. (1994). J. Pharm. Sci. 3, 197–205. CAS Google Scholar
Kimura, H., Katoh, T., Kajimoto, T., Node, M., Hisaki, M., Sugimoto, Y., Majima, T., Uehara, Y. & Yamori, T. (2006). Anticancer Res. 26, 91–97. Web of Science PubMed CAS Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
McKinnon, J. J., Fabbiani, F. P. & Spackman, M. A. (2007). Cryst. Growth Des. 7, 755–769. CrossRef CAS Google Scholar
Nammalwar, B., Bunce, R. A., Berlin, K. D., Bourne, C. R., Bourne, P. C., Barrow, E. W. & Barrow, W. W. (2012). Eur. J. Med. Chem. 54, 387–396. CrossRef CAS Google Scholar
Nelson, R. G. & Rosowsky, A. (2001). Antimicrob. Agents Chemother. 45, 3293–3303. CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Subasri, S., Kumar, T. A., Sinha, B. N., Jayaprakash, V. & Velmurugan, D. (2014). Acta Cryst. E70, o850. CSD CrossRef IUCr Journals Google Scholar
Subasri, S., Kumar, T. A., Sinha, B. N., Jayaprakash, V., Viswanathan, V. & Velmurugan, D. (2017a). Acta Cryst. E73, 306–309. CrossRef IUCr Journals Google Scholar
Subasri, S., Kumar, T. A., Sinha, B. N., Jayaprakash, V., Viswanathan, V. & Velmurugan, D. (2017b). Acta Cryst. E73, 467–471. CrossRef IUCr Journals Google Scholar
Subasri, S., Timiri, A. K., Barji, N. S., Jayaprakash, V., Vijayan, V. & Velmurugan, D. (2016). Acta Cryst. E72, 1171–1175. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhou, W., Huang, A., Zhang, Y., Lin, Q., Guo, W., You, Z., Yi, Z., Liu, M. & Chen, Y. (2015). Eur. J. Med. Chem. 96, 269–280. CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 74| Part 5| May 2018| Pages 718-723

https://doi.org/10.1107/S2056989018005704

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text
		Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text
		Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structures and Hirshfeld surface analyses of 2-[(4,6-di­amino­pyrimidin-2-yl)sulfan­yl]-N-(pyridin-2-yl)acetamide and 2-[(4,6-di­amino­pyrimidin-2-yl)sulfan­yl]-N-(pyrazin-2-yl)acetamide

1. Chemical context

2. Structural commentary

3. Supra­molecular features

4. Database survey

5. Hirshfeld surface analysis

6. Synthesis and crystallization

7. Refinement

Supporting information

Acknowledgements

Funding information

References

research communications

Crystal structures and Hirshfeld surface analyses of 2-[(4,6-diaminopyrimidin-2-yl)sulfanyl]-N-(pyridin-2-yl)acetamide and 2-[(4,6-diaminopyrimidin-2-yl)sulfanyl]-N-(pyrazin-2-yl)acetamide

3. Supramolecular features