Crystal structure and Hirshfeld surface analysis of 1-(2-amino-4-methyl-1,3-thia­zol-5-yl)ethan-1-one

Huseynov, E.Z.; Akkurt, M.; Brito, I.; Bhattarai, A.; Rzayev, R.M.; Asadov, K.A.; Maharramov, A.M.

doi:10.1107/S2056989023007181

research communications

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 79| Part 10| October 2023| Pages 890-894

https://doi.org/10.1107/S2056989023007181

Open

access

Crystal structure and Hirshfeld surface analysis of 1-(2-amino-4-methyl-1,3-thiazol-5-yl)ethan-1-one

Elnur Z. Huseynov,^a Mehmet Akkurt,^b Ivan Brito,^c Ajaya Bhattarai,^d ^* Rovnag M. Rzayev,^e Khammed A. Asadov ^a and Abel M. Maharramov ^a

^aDepartment of Chemistry, Baku State University, Z. Khalilov str. 23, Az, 1148 Baku, Azerbaijan, ^bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Türkiye, ^cDepartamento de Química, Facultad de Ciencias Básicas, Universidad de Antofagasta, Avenida Angamos 601, Casilla 170, Antofagasta 1240000, Chile, ^dDepartment of Chemistry, M.M.A.M.C. (Tribhuvan University) Biratnagar, Nepal, and ^e"Composite Materials" Scientific Research Center, Azerbaijan State Economic University (UNEC), H. Aliyev str. 135, Az1063, Baku, Azerbaijan
^*Correspondence e-mail: ajaya.bhattarai@mmamc.tu.edu.np

Edited by L. Van Meervelt, Katholieke Universiteit Leuven, Belgium (Received 4 August 2023; accepted 16 August 2023; online 8 September 2023)

In the title compound, C₆H₈N₂OS, all atoms except for the methyl H atoms are coplanar, with a maximum deviation of 0.026 (4) Å. In the crystal, pairs of molecules are linked by N—H⋯N hydrogen bonds, forming R²₂(8) ring motifs. Dimers are connected by N—H⋯O hydrogen bonds, forming layers parallel to the (102) plane. Consolidating the molecular packing, these layers are connected by C—H⋯π interactions between the center of the 1,3-thiazole ring and the H atom of the methyl group attached to it, as well as C=O⋯π interactions between the center of the 1,3-thiazole ring and the O atom of the carboxyl group. According to a Hirshfeld surface study, H⋯H (37.6%), O⋯H/H⋯O (16.8%), S⋯H/H⋯S (15.4%), N⋯H/H⋯N (13.0%) and C⋯H/H⋯C (7.6%) interactions are the most significant contributors to the crystal packing.

Keywords: crystal structure; thiazole derivatives; hydrogen bonds; dimers; Hirshfeld surface analysis.

CCDC reference: 2288949

1. Chemical context

Heterocyclic aromatic systems are the most important and manifold compounds in organic chemistry (Maharramov et al., 2011b ; Abdelhamid et al., 2014 ). Organic synthesis is developing intensely with newer aromatic heterocyclic compounds that are obtained for diverse medicinal and commercial purposes (Khalilov et al., 2021 ). Nowadays, applications of five- and six-membered ring heterocycles have expanded in different branches of chemistry, including sustainable chemistry (Montes et al., 2018 ), drug design and development (Tas et al., 2023 ) and materials sciences (Yin et al., 2020 ). The thiazole core is the most common five-membered heteroaromatic ring system in azole heterocycles (Yadigarov et al., 2009 ; Khalilov, 2021 ). Thiazoles have potent medicinal applications as it is an essential core scaffold present in many natural (thiamine, penicillin) and synthetic medicinally important compounds (Chhabria et al., 2016 ) such as sulfazole, ritonavir, abafungin, fanetizole, meloxicam, fentiazac, nizatidine, thiamethoxam, etc. (Fig. 1). On the other hand, there have been a variety of significant examples of thiazole derivatives used as target products as well as synthetic intermediates (Akkurt et al., 2018 ; Kekeçmuhammed et al., 2022 ).

Figure 1
Some marketed drugs containing the thiazole moiety.

In a continuation of our investigations of heterocyclic systems with biological activity and in the framework of ongoing structural studies (Maharramov et al., 2011a ; Askerov et al., 2020 ; Karimli et al., 2023 ), we report here the crystal structure and Hirshfeld surface analysis of the title compound, 1-(2-amino-4-methyl-1,3-thiazol-5-yl)ethan-1-one.

2. Structural commentary

In the title compound, Fig. 2, all atoms except for the methyl H atoms are coplanar, with a maximum deviation of 0.026 (4) Å for C6. The geometric parameters of the title compound are normal and comparable to those of related compounds listed in the Database survey section.

Figure 2
The molecular structure of the title compound, showing the atom labeling and displacement ellipsoids drawn at the 50% probability level.

3. Supramolecular features and Hirshfeld surface analysis

In the crystal, pairs of molecules are linked by N—H⋯N hydrogen bonds, forming $[R_{2}^{2}]$ (8) ring motifs (Bernstein et al., 1995 ; Table 1, Fig. 3). Dimers are connected by N—H⋯O hydrogen bonds, forming layers parallel to the (102) plane (Table 1, Fig. 4). Consolidating the molecular packing, these layers are connected by C—H⋯π interactions between the center of the 1,3-thiazole ring and the H atom of the methyl group attached to it, as well as C=O⋯π interactions between the center of the 1,3-thiazole ring and the O atom of the carboxyl group (Table 1, Figs. 5 and 6).

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the (N1/S1/C1–C3) 1,3-thiazole ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1A⋯N1ⁱ	0.86	2.11	2.963 (4)	175
N2—H1B⋯O1ⁱⁱ	0.86	2.02	2.835 (4)	158
C4—H4B⋯Cg1ⁱⁱⁱ	0.96	2.89	3.603 (4)	132
Symmetry codes: (i) ; (ii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Figure 3
Partial view of the N—H⋯N and N—H⋯O bonds in the (102) plane of the title compound.

Figure 4
View of the packing of the title compound along the b-axis.

Figure 5
View of the C—H⋯π and C=O⋯π interactions of the title compound down the a axis.

Figure 6
View of the C—H⋯π and C=O⋯π interactions of the title compound down the b axis.

Crystal Explorer 17.5 (Spackman et al., 2021 ) was used to generate Hirshfeld surfaces and two-dimensional fingerprint plots in order to quantify the intermolecular interactions in the crystal. The Hirshfeld surfaces were mapped over d_norm in the range −0.5624 (red) to 0.9850 (blue) a.u. (Fig. 7). The interactions given in Table 2 play a key role in the molecular packing of the title compound. The most important interatomic contact is H⋯H as it makes the highest contribution to the crystal packing (37.6%, Fig. 8b). Other major contributors are O⋯H/H⋯O (16.8%, Fig. 8c), S⋯H/H⋯S (15.4%, Fig. 8d), N⋯H/H⋯N (13.0%, Fig. 8e) and C⋯H/H⋯C (7.6%, Fig. 8f) interactions. Other, smaller contributions are made by S⋯C/C⋯S (2.7%), C⋯O/O⋯C (2.6%), C⋯C (1.8%), N⋯C/C⋯N (1.5%), S⋯O/O⋯S (0.8%), S⋯N/N⋯S (0.1%) and O⋯N/N⋯O (0.1%) interactions.

Table 2
Summary of short interatomic contacts (Å) in the title compound

O1⋯H4A	2.69	1 + x, y, z
O1⋯H1B	2.02	2 − x, $[{1\over 2}]$ + y, $[{1\over 2}]$ − z
C1⋯H4B	3.09	x, $[{3\over 2}]$ − y, − $[{1\over 2}]$ + z
H1A⋯N1	2.11	1 − x, 1 − y, 1 − z
N2⋯H6B	2.89	1 − x, − $[{1\over 2}]$ + y, $[{1\over 2}]$ − z

Figure 7
(a) Front and (b) back sides of the three-dimensional Hirshfeld surface of the title compound mapped over d_norm, with a fixed color scale of −0.5624 to 0.9850 a.u.

Figure 8
The two-dimensional fingerprint plots of the title compound, showing (a) all interactions, and delineated into (b) H⋯H, (c) O⋯H/H⋯O, (d) S⋯H/H⋯S, (e) N⋯H/H⋯N and (f) C⋯H/H⋯C interactions. [d_e and d_i represent the distances from a point on the Hirshfeld surface to the nearest atoms outside (external) and inside (internal) the surface, respectively].

4. Database survey

A search of the Cambridge Structural Database (CSD, Version 5.43, last update November 2022; Groom et al., 2016 ) for the central five-membered ring 1,3-thiazole yielded five compounds related to the title compound, viz. CSD refcodes IXAMAV (Kennedy et al., 2004a ), ABEGAQ (Kennedy et al., 2004b ), FEFKUY (Hazra et al., 2012 ), DUTZEY (Chen & Xu, 2010 ) and LAMQOJ (Fait et al., 2021 ).

In the crystal of IXAMAV, the supramolecular network is based upon N—H⋯N hydrogen-bonded centrosymmetric dimers linked by N—H⋯O contacts. ABEGAQ forms a supramolecular network based on N—H⋯N hydrogen-bonded centrosymmetric dimers that are linked in turn by N—H⋯O contacts. In the crystal of FEFKUY, an interplay of O—H⋯N and C—H⋯O hydrogen bonds connects the molecules to form C(6) $[R_{2}^{2}]$ (8) polymeric chains, which are further linked via weak C—H⋯O hydrogen bonds into a two-dimensional supramolecular framework. The crystal structure of DUTZEY involves intermolecular N—H⋯N hydrogen bonds. In the crystal of LAMQOJ, weak C—H⋯N hydrogen bonds build up a wavy layer of molecules in the (011) plane. The layers are stacked in the [100] direction by weak π–π stacking interactions between the 1,3-thiazole rings.

5. Synthesis and crystallization

The title compound was synthesized using a reported procedure (Donald et al., 2012 ), and colorless crystals were obtained upon recrystallization from an ethanol/water (3:1) solution at room temperature.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. All H atoms were placed in calculated positions (C—H = 0.96 Å and N—H = 0.86 Å) and refined as riding with U_iso(H) = 1.2U_eq(N) for the NH₂ group and 1.5U_eq(C) for CH₃ groups.

Table 3
Experimental details

Crystal data
Chemical formula	C₆H₈N₂OS
M_r	156.20
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	6.7445 (15), 13.498 (3), 8.010 (2)
β (°)	94.421 (7)
V (Å³)	727.1 (3)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.37
Crystal size (mm)	0.60 × 0.45 × 0.35

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Krause et al., 2015
T_min, T_max	0.649, 0.745
No. of measured, independent and observed [I > 2σ(I)] reflections	14701, 1492, 940
R_int	0.144
(sin θ/λ)_max (Å⁻¹)	0.626

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.142, 1.04
No. of reflections	1492
No. of parameters	93
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.28
Computer programs: APEX2 and SAINT (Bruker, 2016 ), SHELXT2018/2 (Sheldrick, 2015a ), SHELXL2018/3 (Sheldrick, 2015b ), ORTEP-3 for Windows (Farrugia, 2012 ) and PLATON (Spek, 2020 ).

Supporting information

CCDC reference: 2288949

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989023007181/vm2288sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989023007181/vm2288Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989023007181/vm2288Isup3.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2016); cell refinement: SAINT V8.40B (Bruker, 2016); data reduction: SAINT V8.40B (Bruker, 2016); program(s) used to solve structure: SHELXT2018/2 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2020).

1-(2-Amino-4-methyl-1,3-thiazol-5-yl)ethan-1-one top

Crystal data top

C₆H₈N₂OS	F(000) = 328
M_r = 156.20	D_x = 1.427 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 6.7445 (15) Å	Cell parameters from 2051 reflections
b = 13.498 (3) Å	θ = 3.0–26.4°
c = 8.010 (2) Å	µ = 0.37 mm⁻¹
β = 94.421 (7)°	T = 296 K
V = 727.1 (3) Å³	Prism, colourless
Z = 4	0.60 × 0.45 × 0.35 mm

Data collection top

Bruker APEXII CCD diffractometer	940 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.144
Absorption correction: multi-scan (SADABS; Krause et al., 2015	θ_max = 26.4°, θ_min = 3.0°
T_min = 0.649, T_max = 0.745	h = −8→8
14701 measured reflections	k = −16→16
1492 independent reflections	l = −10→10

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.050	H-atom parameters constrained
wR(F²) = 0.142	w = 1/[σ²(F_o²) + (0.0616P)² + 0.4474P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
1492 reflections	Δρ_max = 0.29 e Å⁻³
93 parameters	Δρ_min = −0.28 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	0.5920 (5)	0.7303 (2)	0.4486 (4)	0.0354 (8)
C2	0.7302 (5)	0.5848 (2)	0.4036 (4)	0.0356 (8)
C3	0.7583 (5)	0.7636 (2)	0.3769 (4)	0.0349 (8)
C4	0.4274 (5)	0.7905 (3)	0.5084 (5)	0.0446 (9)
H4A	0.356539	0.822440	0.414759	0.067*
H4B	0.480953	0.839710	0.585759	0.067*
H4C	0.338231	0.748209	0.563299	0.067*
C5	0.8348 (5)	0.8605 (3)	0.3393 (4)	0.0408 (9)
C6	0.7269 (6)	0.9538 (3)	0.3790 (5)	0.0567 (11)
H6A	0.718170	0.958584	0.497742	0.085*
H6B	0.595477	0.952624	0.323674	0.085*
H6C	0.798079	1.010036	0.340806	0.085*
N1	0.5761 (4)	0.62959 (19)	0.4631 (4)	0.0359 (7)
N2	0.7505 (4)	0.4865 (2)	0.4051 (4)	0.0498 (9)
H1A	0.661573	0.449933	0.445684	0.060*
H1B	0.852593	0.459698	0.365376	0.060*
S1	0.90402 (13)	0.66254 (6)	0.32437 (12)	0.0412 (3)
O1	0.9925 (4)	0.8657 (2)	0.2713 (4)	0.0571 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0349 (18)	0.0323 (17)	0.039 (2)	0.0005 (15)	0.0045 (15)	−0.0011 (15)
C2	0.0348 (18)	0.0287 (16)	0.044 (2)	0.0034 (14)	0.0063 (15)	0.0031 (15)
C3	0.0343 (18)	0.0308 (17)	0.040 (2)	−0.0023 (14)	0.0035 (15)	0.0009 (15)
C4	0.042 (2)	0.0320 (18)	0.061 (2)	0.0032 (16)	0.0105 (18)	−0.0005 (17)
C5	0.0410 (19)	0.0351 (19)	0.046 (2)	−0.0044 (15)	0.0016 (17)	0.0066 (15)
C6	0.066 (3)	0.0313 (19)	0.075 (3)	0.0012 (19)	0.015 (2)	0.0054 (19)
N1	0.0318 (14)	0.0294 (14)	0.0476 (18)	−0.0007 (11)	0.0093 (13)	0.0001 (13)
N2	0.0450 (18)	0.0295 (16)	0.078 (2)	0.0006 (13)	0.0263 (17)	0.0004 (15)
S1	0.0371 (5)	0.0341 (5)	0.0547 (6)	0.0002 (4)	0.0172 (4)	0.0035 (4)
O1	0.0474 (16)	0.0460 (16)	0.080 (2)	−0.0083 (12)	0.0182 (15)	0.0148 (14)

Geometric parameters (Å, º) top

C1—N1	1.370 (4)	C4—H4B	0.9600
C1—C3	1.375 (4)	C4—H4C	0.9600
C1—C4	1.484 (5)	C5—O1	1.234 (4)
C2—N1	1.322 (4)	C5—C6	1.501 (5)
C2—N2	1.334 (4)	C6—H6A	0.9600
C2—S1	1.730 (3)	C6—H6B	0.9600
C3—C5	1.446 (5)	C6—H6C	0.9600
C3—S1	1.752 (3)	N2—H1A	0.8600
C4—H4A	0.9600	N2—H1B	0.8600

N1—C1—C3	115.6 (3)	O1—C5—C3	118.5 (3)
N1—C1—C4	116.8 (3)	O1—C5—C6	119.6 (3)
C3—C1—C4	127.6 (3)	C3—C5—C6	121.9 (3)
N1—C2—N2	122.3 (3)	C5—C6—H6A	109.5
N1—C2—S1	115.4 (2)	C5—C6—H6B	109.5
N2—C2—S1	122.3 (2)	H6A—C6—H6B	109.5
C1—C3—C5	134.3 (3)	C5—C6—H6C	109.5
C1—C3—S1	109.7 (2)	H6A—C6—H6C	109.5
C5—C3—S1	116.0 (2)	H6B—C6—H6C	109.5
C1—C4—H4A	109.5	C2—N1—C1	110.7 (3)
C1—C4—H4B	109.5	C2—N2—H1A	120.0
H4A—C4—H4B	109.5	C2—N2—H1B	120.0
C1—C4—H4C	109.5	H1A—N2—H1B	120.0
H4A—C4—H4C	109.5	C2—S1—C3	88.60 (15)
H4B—C4—H4C	109.5

N1—C1—C3—C5	−179.3 (4)	N2—C2—N1—C1	179.3 (3)
C4—C1—C3—C5	2.0 (7)	S1—C2—N1—C1	−0.5 (4)
N1—C1—C3—S1	0.0 (4)	C3—C1—N1—C2	0.3 (5)
C4—C1—C3—S1	−178.7 (3)	C4—C1—N1—C2	179.2 (3)
C1—C3—C5—O1	−179.5 (4)	N1—C2—S1—C3	0.4 (3)
S1—C3—C5—O1	1.3 (5)	N2—C2—S1—C3	−179.4 (3)
C1—C3—C5—C6	−0.1 (7)	C1—C3—S1—C2	−0.2 (3)
S1—C3—C5—C6	−179.4 (3)	C5—C3—S1—C2	179.2 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the (N1/S1/C1–C3) 1,3-thiazole ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1A···N1ⁱ	0.86	2.11	2.963 (4)	175
N2—H1B···O1ⁱⁱ	0.86	2.02	2.835 (4)	158
C4—H4B···Cg1ⁱⁱⁱ	0.96	2.89	3.603 (4)	132

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

Summary of short interatomic contacts (Å) in the title compound top

O1···H4A	2.69	1 + x, y, z
O1···H1B	2.02	2 - x, 1/2 + y, 1/2 - z
C1···H4B	3.09	x, 3/2 - y, -1/2 + z
H1A···N1	2.11	1 - x, 1 - y, 1 - z
N2···H6B	2.89	1 - x, -1/2 + y, 1/2 - z

Acknowledgements

This study was supported by Baku State University, Erciyes University, Tribhuvan University and the Universidad de Antofagasta. Authors' contributions are as follows. Conceptualization, EZH, KAA and AMM; methodology, EZH, IB and MA; investigation, EZH and IB; writing (original draft), MA and AB; writing (review and editing of the manuscript), MA and EZH; visualization, MA, RMR and IB; funding acquisition, EZH, AB and IB; resources, AB, IB and MA; supervision, MA and AMM.

References

Abdelhamid, A. A., Mohamed, S. K., Maharramov, A. M., Khalilov, A. N. & Allahverdiev, M. A. (2014). J. Saudi Chem. Soc. 18, 474–478. Web of Science CSD CrossRef Google Scholar
Akkurt, M., Duruskari, G. S., Toze, F. A. A., Khalilov, A. N. & Huseynova, A. T. (2018). Acta Cryst. E74, 1168–1172. Web of Science CSD CrossRef IUCr Journals Google Scholar
Askerov, R. K., Maharramov, A. M., Khalilov, A. N., Akkurt, M., Akobirshoeva, A. A., Osmanov, V. K. & Borisov, A. V. (2020). Acta Cryst. E76, 1007–1011. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2016). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin. USA. Google Scholar
Chen, X. & Xu, L. (2010). Acta Cryst. E66, o2148. Web of Science CSD CrossRef IUCr Journals Google Scholar
Chhabria, M. T., Patel, S., Modi, P. & Brahmkshatriya, P. S. (2016). Curr. Top. Med. Chem. 16, 2841–2862. Web of Science CAS PubMed Google Scholar
Donald, M. B., Rodriguez, K. X., Shay, H., Phuan, P.-W., Verkman, A. S. & Kurth, M. J. (2012). Bioorg. Med. Chem. 20, 5247–5253. Web of Science CrossRef CAS PubMed Google Scholar
Fait, M. J. G., Spannenberg, A., Kondratenko, E. V. & Linke, D. (2021). IUCrData, 6, x211332. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS 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 CrossRef IUCr Journals Google Scholar
Hazra, D. K., Mukherjee, M., Helliwell, M. & Mukherjee, A. K. (2012). Acta Cryst. C68, o452–o455. Web of Science CSD CrossRef IUCr Journals Google Scholar
Karimli, E. G., Khrustalev, V. N., Kurasova, M. N., Akkurt, M., Khalilov, A. N., Bhattarai, A. & Mamedov, İ. G. (2023). Acta Cryst. E79, 474–477. Web of Science CSD CrossRef IUCr Journals Google Scholar
Kekeçmuhammed, H., Tapera, M., Tüzün, B., Akkoç, S., Zorlu, Y. & Sarıpınar, E. (2022). ChemistrySelect, 7, e202201502. Google Scholar
Kennedy, A. R., Khalaf, A. I., Suckling, C. J. & Waigh, R. D. (2004a). Acta Cryst. E60, o1188–o1190. Web of Science CSD CrossRef IUCr Journals Google Scholar
Kennedy, A. R., Khalaf, A. I., Suckling, C. J. & Waigh, R. D. (2004b). Acta Cryst. E60, o1510–o1512. Web of Science CSD CrossRef IUCr Journals Google Scholar
Khalilov, A. N. (2021). Rev. Roum. Chim. 66, 719–723. Google Scholar
Khalilov, A. N., Tüzün, B., Taslimi, P., Tas, A., Tuncbilek, Z. & Cakmak, N. K. (2021). J. Mol. Liq. 344, 117761. Web of Science CrossRef Google Scholar
Krause, L., Herbst-Irmer, R., Sheldrick, G. M. & Stalke, D. (2015). J. Appl. Cryst. 48, 3–10. Web of Science CSD CrossRef ICSD CAS IUCr Journals Google Scholar
Maharramov, A. M., Khalilov, A. N., Gurbanov, A. V., Allahverdiyev, M. A. & Ng, S. W. (2011a). Acta Cryst. E67, o721. Web of Science CSD CrossRef IUCr Journals Google Scholar
Maharramov, A. M., Khalilov, A. N., Gurbanov, A. V. & Brito, I. (2011b). Acta Cryst. E67, o1307. Web of Science CSD CrossRef IUCr Journals Google Scholar
Montes, V., Miñambres, J. F., Khalilov, A. N., Boutonnet, M., Marinas, J. M., Urbano, F. J., Maharramov, A. M. & Marinas, A. (2018). Catal. Today, 306, 89–95. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Spackman, P. R., Turner, M. J., McKinnon, J. J., Wolff, S. K., Grimwood, D. J., Jayatilaka, D. & Spackman, M. A. (2021). J. Appl. Cryst. 54, 1006–1011. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2020). Acta Cryst. E76, 1–11. Web of Science CrossRef IUCr Journals Google Scholar
Tas, A., Tüzün, B., Khalilov, A. N., Taslimi, P., Ağbektas, T. & Cakmak, N. K. (2023). J. Mol. Struct. 1273, 134282. Web of Science CrossRef Google Scholar
Yadigarov, R. R., Khalilov, A. N., Mamedov, I. G., Nagiev, F. N., Magerramov, A. M. & Allakhverdiev, M. A. (2009). Russ. J. Org. Chem. 45, 1856–1858. Web of Science CrossRef CAS Google Scholar
Yin, J., Khalilov, A. N., Muthupandi, P., Ladd, R. & Birman, V. B. (2020). J. Am. Chem. Soc. 142, 60–63. Web of Science CSD CrossRef CAS PubMed 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 79| Part 10| October 2023| Pages 890-894

https://doi.org/10.1107/S2056989023007181

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 structure and Hirshfeld surface analysis of 1-(2-amino-4-methyl-1,3-thia­zol-5-yl)ethan-1-one

1. Chemical context

2. Structural commentary

3. Supra­molecular features and Hirshfeld surface analysis

4. Database survey

5. Synthesis and crystallization

6. Refinement

Supporting information

Acknowledgements

References

research communications

Crystal structure and Hirshfeld surface analysis of 1-(2-amino-4-methyl-1,3-thiazol-5-yl)ethan-1-one

3. Supramolecular features and Hirshfeld surface analysis