Consistent supra­molecular motifs and different local symmetries in the structures of 2-amino-5-(4-fluoro­phen­yl)-1,3-thia­zole-4-carbaldehyde and 2-amino-5-(4-chloro­phen­yl)-1,3-thia­zole-4-carbaldehyde

Guseinov, F.I.; Afanaseva, K.A.; Gaidar, S.M.; Pikina, A.M.; Akkurt, M.; Aliyeva, F.S.; Hasanov, K.I.; Belay, A.N.

doi:10.1107/S2056989025010667

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ISSN: 2056-9890

Volume 82| Part 1| January 2026| Pages 14-18

https://doi.org/10.1107/S2056989025010667

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Consistent supramolecular motifs and different local symmetries in the structures of 2-amino-5-(4-fluorophenyl)-1,3-thiazole-4-carbaldehyde and 2-amino-5-(4-chlorophenyl)-1,3-thiazole-4-carbaldehyde

Firudin I. Guseinov,^a,^b Ksenia A. Afanaseva,^a,^b Sergey M. Gaidar,^c Anna M. Pikina,^c Mehmet Akkurt,^d Fargana S. Aliyeva,^e Khudayar I. Hasanov ^f and Alebel N. Belay ^g ^*

^aKosygin State University of Russia, 117997 Moscow, Russian Federation, ^bN.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian Federation, ^cRussian State Agrarian University-Moscow Timiryazev Agricultural Academy, 127550 Moscow, Russian Federation, ^dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Türkiye, ^eExcellence Center, Baku State University, Z. Xalilov Str. 23, Az 1148 Baku, Azerbaijan, ^fAzerbaijan Medical University, Scientific Research Centre (SRC), Kasumzade St. 14. AZ 1022, Baku, Azerbaijan, and ^gDepartment of Chemistry, Bahir Dar University, PO Box 79, Bahir Dar, Ethiopia
^*Correspondence e-mail: [email protected]

Edited by W. T. A. Harrison, University of Aberdeen, United Kingdom (Received 17 September 2025; accepted 29 November 2025; online 1 January 2026)

The first title compound, C₁₀H₇FN₂OS, crystallizes in space group P1 with two independent molecules in the asymmetric unit, which form a dimer with an R²₂(8) motif through pairwise N—H⋯N hydrogen bonds. In the crystal of (I), N—H⋯O hydrogen bonds bind the dimers into zigzag ribbons running along the [100] direction, generating R⁴₄(14) motifs. The second title compound, C₁₀H₇ClN₂OS (space group I2/a), contains one molecule in the asymmetric unit, which forms a dimer with an R²₂(8) motif via inversion symmetry. In the extended structure, the molecules form zigzag ribbons in the [100] direction by N—H⋯N and N—H⋯O hydrogen bonds, resulting in consecutive R⁴₁(8)R²₁(5)R²₂(8)R²₁(5)R⁴₁(8) motifs. The Hirshfeld surface analyses of the compounds (I) and (II) indicates that the most important factors influencing the crystal packing are H⋯H interactions [21.1% for molecule A of (I), 20.3% for molecule B of (I) and 21.0% for (II)].

Keywords: crystal structure; 1,3-thiazole ring; haloketones; halooxiranes.

CCDC references: 2512074; 2512073

1. Chemical context

Thiazole and its derivatives are known for their broad spectrum of biological applications, such as antimicrobial, anti-inflammatory, antiviral, antitubercular and CNS active agents and for their anticancer activities (Basarab et al., 2012 ; Shaikh et al., 2023 ). It should be noted that the thiazole-4-carbaldehyde fragment is part of the natural polyketide thuggacin A, which has high anti-tuberculosis activity (Liu et al., 2025 ). Earlier, we showed that acetal-containing chlorooxiranes and their isomeric chloroketones are effective starting reagents for obtaining heterocyclic systems, in particular, heterocyclic aldehydes (Guseinov & Yudina, 1998 ; Guseinov et al., 2017 ).

In this work, we describe a one-step synthetic protocol to access 2-amino-5-(4-halophenyl)thiazole-4-carbaldehydes and a study of their structural features using X-ray diffraction.

2. Structural commentary

Compound (I) crystallizes in the triclinic space group P $[\overline{1}]$ with two crystallographically independent molecules, A and B, in the asymmetric unit (Fig. 1). An overlay fit of inverted molecule B on molecule A is shown in supplementary Fig. S1: the weighted r.m.s. fit of the 15 non-H atoms being 0.114 Å with the major differences being in the terminal benzene rings of molecules A and B. The dihedral angle between the planes of the five and six-membered rings is 61.74 (8)° for A and 57.07 (8)° for B. Selected bond lengths include C9A—F9A = 1.3580 (18) Å for molecule A and C9B—F9B = 1.3626 (17) Å for molecule B. The C—N bond lengths in the five-membered rings are C2A—N3A = 1.308 (2) and C4A—N3A = 1.384 (2) Å for A and C2B—N3B = 1.309 (2) and C4B—N3B = 1.388 (2) Å for B. The C—N bond length attached to the five-membered ring of the NH₂ group is C2A—N12A = 1.343 (2) Å for A and C2B—N12B = 1.344 (2) Å for B.

Figure 1
The asymmetric unit of (I)

with displacement ellipsoids drawn at the 50% probability level.

Compound (II), which crystallizes in space group I2/a with one molecule in the asymmetric unit (Fig. 2) has a non planar conformation in which the dihedral angle between the planes of the benzene and 1,3-thiazole rings is 56.50 (8)°. The torsion angles S1—C5—C6—C7 and C4—C5—C6—C11 are −57.7 (2) and −53.7 (3)°, respectively. The C—N lengths [C2—N3 and C4—N3] in the five-membered ring are 1.307 (2) and 1.386 (2) Å, respectively. The C—N length [C2—N12] for the NH₂ group attached to the ring is 1.346 (2) Å and the C9—Cl9 bond length is 1.7410 (16) Å.

Figure 2
The asymmetric unit of (II)

with displacement ellipsoids drawn at the 50% probability level.

Otherwise, the bond lengths and angles in compounds (I) and (II) are normal and can be compared with each other and with those in the Database Survey section.

3. Supramolecular features and Hirshfeld surface analyses

The two independent molecules (A and B) in the asymmetric unit of (I) form a dimer with an R₂²(8) motif through pairwise N—H⋯N hydrogen bonds (Table 1). In the crystal, N—H⋯O hydrogen bonds link the dimers into zigzag ribbons extending along the [100] direction, producing R₄⁴(14) motifs between them (Fig. 3). Additionally, the molecules in these ribbons form R₂³(11) motifs through C—H⋯S and C—H⋯F interactions, resulting in a three-dimensional supramolecular network. A weak C—H⋯π interaction also occurs (supplementary Figs. S2–S4).

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N12A—H12A⋯N3B	0.87 (2)	2.16 (3)	3.0121 (19)	167 (2)
N12A—H12B⋯O14Aⁱ	0.86 (2)	2.13 (2)	2.9596 (19)	160 (2)
N12B—H12C⋯O14Bⁱⁱ	0.82 (2)	2.16 (2)	2.9433 (19)	161 (2)
N12B—H12D⋯N3A	0.87 (3)	2.13 (3)	2.9778 (19)	164 (2)
C8A—H8A⋯S1Bⁱⁱⁱ	0.95	2.91	3.6376 (16)	134
C8B—H8B⋯N3A^iv	0.95	2.68	3.521 (2)	149
C13B—H13B⋯F9A^v	0.95	2.60	3.4911 (19)	157
C7B—H7B⋯Cg3^iv	0.95	2.75	3.4117 (17)	127
Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .

Figure 3
Partial packing diagram for (I)

showing ribbons extending along the [100] direction with an [ R₂²(8) R₄⁴(14)]_n motif formed by N—H⋯N and N—H⋯O hydrogen bonds. Symmetry codes: (i) x + 1, y, z; (iii) x - 1, y, z.

In the extended structure of (II), the molecules are linked through N—H⋯N and N—H⋯O hydrogen bonds (Table 2), forming zigzag ribbons propagating along the [100] direction, generating successive R₁⁴(8) R₁²(5) R₂²(8) R₁²(5) R₁⁴(8) motifs (Fig. 4). In addition, π–π [Cg2⋯Cg2^a = 3.8099 (11) Å, slippage = 1.011 Å; symmetry code (a) $[{3\over 2}]$ − x, y, 1 − z; Cg2 is the centroid of the (C6–C11) benzene ring] and C—Cl⋯π interactions (Table 1) connect these ribbons along the [010] and [001] directions to generate a three-dimensional supramolecular network (supplementary Figs. S5–S7).

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N12—H12A⋯N3ⁱ	0.84 (3)	2.19 (3)	3.015 (2)	167 (2)
N12—H12A⋯O14ⁱ	0.84 (3)	2.61 (3)	3.1222 (19)	121 (2)
N12—H12B⋯O14ⁱⁱ	0.81 (3)	2.18 (3)	2.940 (2)	159 (2)
C9—Cl9⋯Cg1ⁱⁱⁱ	1.74 (1)	3.53 (1)	4.5317 (19)	114 (1)
Symmetry codes: (i) ; (ii) $[x+{\script{1\over 2}}, -y+1, z]$ ; (iii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Figure 4
A partial view of the packing of (II)

showing N—H⋯N and N—H⋯O hydrogen bonds, forming zigzag ribbons propagating along the [100] direction, with successive [ R₁⁴(8) R₁²(5) R₂²(8) R₁²(5) R₁⁴(8)]_n motifs. Symmetry codes: (i) −x + 1, −y + 1, −z; (ii) x + $[{1\over 2}]$ , −y + 1, z; (iii) x + $[{1\over 2}]$ , −y + 1, z.

Crystal Explorer 21 (Spackman et al., 2021 ) was used to construct Hirshfeld surfaces for both independent molecules A and B in the asymmetric unit of compound (I). The d_norm mappings for molecule A were performed in the range of −0.49 to +1.11 a.u., and for molecule B in the range of −0.49 to +1.11 a.u. On the d_norm surfaces, bold red circles show the locations of N—H⋯O and N—H⋯N interactions (Fig. 5). Smaller red spots are caused by the C—H⋯S interactions.

Figure 5
View of the three-dimensional Hirshfeld surfaces of the molecules A (a) and B (b) of (I)

, and (c) (II)

plotted over d_norm.

Fingerprint plots (Fig. 6) for (I) reveal that H⋯H (21.1% for molecule A and 20.3% for molecule B) interactions make the largest contributions to the surface contacts and O⋯H/H⋯O (16.0% for A and 13.5% for B), C⋯H/H⋯C (13.1% for A and 16.1% for B), N⋯H/H⋯N (11.7% for A and 13.1% for B) and F⋯H/H⋯F (10.3% for A and 10.2% for B) contacts are also significant. The interactions that have less of an influence include S⋯H/H⋯S (9.7% for A and 6.2% for B), C⋯C (5.6% for A and 5.8% for B), F⋯C/C⋯F (4.3% for A and B), S⋯F/F⋯S (2.6% for A and 3.2% for B), S⋯C/C⋯S (1.9% for A and 2.7% for B), F⋯O/O⋯F (1.0% for A and 0.9% for B), F⋯F (0.6% for A and 0.0% for B) and F⋯N/N⋯F (0.2% for A and B).

Figure 6
Two-dimensional fingerprint plots of molecules A and B of (I)

, and (II)

showing (a) all interactions, and delineated into (b) H⋯H, (c) O⋯H/H⋯O, (d) C⋯H/H⋯C, (e) N⋯H/H⋯N for A and B of (I)

and Cl⋯H/H⋯Cl for (II)

, and (f) F⋯H/H⋯F for A and B of (I)

and S⋯H/H⋯S for (II)

, interactions.

The solid-state consolidation in (II) is significantly impacted by H⋯H interactions, which account for 21.0% of the total. The interactions that have less of an influence include O⋯H/H⋯O (15.3%), C⋯H/H⋯C (12.1%), Cl⋯H/H⋯Cl (9.9%) and S⋯H/H⋯S (7.9%), C⋯C (6.8%), Cl⋯C/C⋯Cl (6.7%), Cl⋯S/S⋯Cl (3.7%), S⋯O / O⋯S (2.1%), Cl⋯Cl (1.8%), Cl⋯N/N⋯Cl (0.8%), N⋯C/C⋯N (0.5%), S⋯S (0.31%) and S⋯C / C⋯S (0.2%).

While the contributions of the strong interactions of (I) and (II) are quite consistent, weak interactions vary slightly depending on the molecular conformation and the environment of the molecules.

4. Database survey

The most closely related ten structures containing a 5-phenyl-1,3-thiazole fragment are as follows: Cambridge Structural Database (CSD, Version 6.00, update of April 2025; Groom et al., 2016 ) refcodes MEFVUS (Guseinov et al., 2022 ), IQUHOT (Saravanan et al., 2016 ), GUVVAW (Akkurt et al., 2015 ), WOJKOX (Mague et al., 2014 ), HOQSAJ (El Ashry et al., 2014 ), SAYXEW (Sun et al., 2006 ), EKEZUP (Rybakov et al., 2003 ), HIYLOQ (Au-Alvarez et al., 1999 ), FUHJIB (Caldwell et al., 1987 ) and CPYPTZ (Le Count & Jarvis, 1977 ).

In the crystal of MEFVUS, C—H⋯π interactions link the molecules, forming a three-dimensional network. In IQUHOT, the molecules are linked via C—H⋯O interactions, which form C(7) chains propagating along [010]. In the crystal of GUVVAW, the molecular packing features C—H⋯O and C—H⋯π interactions, forming a three-dimensional network. In WOJKOX, the two independent molecules are associated via complementary N—H⋯N hydrogen bonds into a dimer. These dimers are associated through weak C— H⋯Cl and C—H⋯S interactions into supramolecular chains propagating along the a-axis direction. In HOQSAJ, molecular pairs connect by forming R₂²(8) motifs via N—H⋯N interactions. A three-dimensional network is established through C—H⋯π and C—Br⋯π interactions. In SAYXEW, similarly to HOQSAJ, molecular pairs come together via N—H⋯N interactions to form R₂²(8) motifs. A three-dimensional network is formed with C—H⋯π interactions. In EKEZUP, molecules form extended chains through O—H⋯N hydrogen bonds. In HIYLOQ, molecules are linked in parallel layers through N—H⋯N and N—H⋯S interactions in the bc plane. The layers are connected by C—H⋯π interactions. In FUHJIB, molecules are connected to each other by forming ribbons in the [110] direction. The molecular packing features C—H⋯O and C—H⋯F interactions. Additional C—F⋯π and C—O⋯π interactions consolidate the packing. In CPYPTZ, molecules are linked in the b-axis direction as C(7) zigzag chains through N—H⋯N interactions. The molecules form a three-dimensional network via C≡C⋯π interactions.

5. Synthesis and crystallization

To a solution of 2-chloro-2-(diethoxymethyl)-3-(4-fluorophenyl)oxirane [also called 1-chloro-3,3-diethoxy-1-(4-fluorophenyl)propan-2-one] (1.00 mmol) in 20 ml of ethanol (95%) was added thiourea (1.00 mmol) and refluxed at 353 K for 2 h (Fig. 7). Then the ethanol was evacuated under vacuum and the resulting yellow powder of (I) was recrystallized from diethyl ether solution. Crystals suitable for X-ray diffraction were obtained by crystallization of this yellow powder from dimethylsulfoxide (DMSO) solution: yield: 91 or 73%; m.p. 378–380 K. Analysis calculated (%) for C₁₀H₇FN₂OS: C 54.05, H 3.17, N 12.61; found C 54.04, H 3.15, N 12.58. ¹H NMR (300MHz, DMSO-d₆): 6.73 (2H, NH2), 7.38–7.75 (4H, Ar), 9.48 (1H, CHO). ¹³C NMR (75MHz, DMSO-d₆): 116.07, 116.51, 124.00, 132.13, 132.30, 136.44, 137.62, 160.66, 165.60, 167.03, 180.12.

Figure 7
Synthesis scheme for (I)

and (II)

2-Chloro-2-(diethoxymethyl)-3-(4-chlorophenyl)oxirane [also called 1-chloro-3,3-diethoxy-1-(4-chlorophenyl)propan-2-one] was used as a starting material in the synthesis of (II), otherwise the synthetic procedure was the same as for (I): yield: 95 or 77%; m.p. 397–398 K. Analysis calculated (%) for C₁₀H₇ClN₂OS: C 50.32, H 2.96, N 11.74; found C 50.28 H 2.95, N 11.70. ¹H NMR (300MHz, DMSO-d₆): 7.51–7.66 (4H, Ar), 8.36 (2H, NH2), 9.48 (1H, CHO). ¹³C NMR (75MHz, DMSO-d₆): 126.18, 129.42, 131.67, 135.08, 135.49, 136.94, 167.45, 179.75.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. The C-bound H atoms were positioned geometrically and refined using a riding model, with C—H = 0.95 Å. The H atoms of the NH₂ groups were found in difference-Fourier maps and their positions were freely refined.

Table 3
Experimental details

	(I)	(II)
Crystal data
Chemical formula	C₁₀H₇FN₂OS	C₁₀H₇ClN₂OS
M_r	222.24	238.69
Crystal system, space group	Triclinic, P $[\overline{1}]$	Monoclinic, I2/a
Temperature (K)	100	100
a, b, c (Å)	7.6272 (1), 9.0292 (1), 14.7403 (3)	13.9857 (2), 9.8459 (1), 15.3349 (2)
α, β, γ (°)	90.567 (1), 98.122 (1), 108.526 (1)	90, 105.170 (1), 90
V (Å³)	951.24 (3)	2038.06 (5)
Z	4	8
Radiation type	Cu Kα	Cu Kα
μ (mm⁻¹)	2.95	5.01
Crystal size (mm)	0.27 × 0.22 × 0.15	0.53 × 0.38 × 0.30

Data collection
Diffractometer	XtaLAB Synergy, Dualflex, HyPix	XtaLAB Synergy, Dualflex, HyPix
Absorption correction	Gaussian (CrysAlis PRO; Rigaku OD, 2025 )	Gaussian (CrysAlisPr; (Rigaku OD, 2025)
T_min, T_max	0.482, 0.642	0.169, 0.859
No. of measured, independent and observed [I > 2σ(I)] reflections	25299, 4097, 3888	13963, 2220, 2165
R_int	0.047	0.043
(sin θ/λ)_max (Å⁻¹)	0.638	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.098, 1.09	0.036, 0.094, 1.07
No. of reflections	4097	2220
No. of parameters	287	144
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)	0.30, −0.32	0.37, −0.37
Computer programs: CrysAlis PRO (Rigaku OD, 2025), SHELXS97 (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ), ORTEP-3 for Windows (Farrugia, 2012 ) and PLATON (Spek, 2020 ).

Supporting information

CCDC references: 2512074; 2512073

Crystal structure: contains datablocks I, II. DOI: https://doi.org/10.1107/S2056989025010667/hb8159sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989025010667/hb8159Isup4.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989025010667/hb8159Isup4.cml

Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S2056989025010667/hb8159IIsup5.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989025010667/hb8159IIsup5.cml

Supplementary Material. DOI: https://doi.org/10.1107/S2056989025010667/hb8159sup6.pdf

checkCIF report

Computing details top

2-Amino-5-(4-fluorophenyl)-1,3-thiazole-4-carbaldehyde (I) top

Crystal data top

C₁₀H₇FN₂OS	Z = 4
M_r = 222.24	F(000) = 456
Triclinic, P1	D_x = 1.552 Mg m⁻³
a = 7.6272 (1) Å	Cu Kα radiation, λ = 1.54184 Å
b = 9.0292 (1) Å	Cell parameters from 15352 reflections
c = 14.7403 (3) Å	θ = 3.0–79.1°
α = 90.567 (1)°	µ = 2.95 mm⁻¹
β = 98.122 (1)°	T = 100 K
γ = 108.526 (1)°	Prism, yellow
V = 951.24 (3) Å³	0.27 × 0.22 × 0.15 mm

Data collection top

XtaLAB Synergy, Dualflex, HyPix diffractometer	4097 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	3888 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.047
Detector resolution: 10.0000 pixels mm^-1	θ_max = 79.8°, θ_min = 3.0°
ω scans	h = −9→9
Absorption correction: gaussian (CrysAlisPro; Rigaku OD, 2025)	k = −11→11
T_min = 0.482, T_max = 0.642	l = −18→18
25299 measured 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)] = 0.036	Hydrogen site location: mixed
wR(F²) = 0.098	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ²(F_o²) + (0.0488P)² + 0.4701P] where P = (F_o² + 2F_c²)/3
4097 reflections	(Δ/σ)_max = 0.001
287 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.32 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
C2A	0.6615 (2)	0.83196 (18)	0.12921 (10)	0.0221 (3)
C2B	0.4924 (2)	0.83630 (18)	0.38518 (10)	0.0213 (3)
C4A	0.3723 (2)	0.77903 (18)	0.05708 (10)	0.0220 (3)
C4B	0.7501 (2)	0.80308 (18)	0.45848 (10)	0.0219 (3)
C5A	0.4497 (2)	0.75647 (19)	−0.01828 (11)	0.0229 (3)
C5B	0.6445 (2)	0.76230 (18)	0.52804 (10)	0.0215 (3)
C6A	0.3598 (2)	0.70487 (19)	−0.11352 (10)	0.0232 (3)
C6B	0.6890 (2)	0.71135 (18)	0.62088 (10)	0.0214 (3)
C7A	0.4107 (2)	0.80140 (19)	−0.18549 (11)	0.0257 (3)
H7A	0.507656	0.899145	−0.173195	0.031*
C7B	0.5773 (2)	0.56850 (19)	0.64774 (11)	0.0238 (3)
H7B	0.474834	0.504211	0.605476	0.029*
C8A	0.3209 (2)	0.7556 (2)	−0.27469 (11)	0.0274 (3)
H8A	0.352042	0.822314	−0.323469	0.033*
C8B	0.6136 (2)	0.51914 (19)	0.73517 (11)	0.0245 (3)
H8B	0.538805	0.421354	0.753172	0.029*
C9A	0.1857 (2)	0.6112 (2)	−0.29078 (11)	0.0271 (3)
C9B	0.7615 (2)	0.6165 (2)	0.79501 (10)	0.0236 (3)
C10A	0.1335 (2)	0.5107 (2)	−0.22235 (12)	0.0276 (3)
H10A	0.040183	0.411258	−0.235969	0.033*
C10B	0.8742 (2)	0.7586 (2)	0.77200 (11)	0.0261 (3)
H10B	0.974704	0.822805	0.815248	0.031*
C11A	0.2213 (2)	0.5591 (2)	−0.13282 (11)	0.0252 (3)
H11A	0.186923	0.492471	−0.084345	0.030*
C11B	0.8374 (2)	0.80602 (19)	0.68379 (11)	0.0241 (3)
H11B	0.913848	0.903551	0.666320	0.029*
C13A	0.1778 (2)	0.7715 (2)	0.05284 (11)	0.0256 (3)
H13A	0.097536	0.741770	−0.004340	0.031*
C13B	0.9386 (2)	0.79426 (19)	0.46269 (11)	0.0244 (3)
H13B	0.993238	0.760225	0.517060	0.029*
F9A	0.09835 (16)	0.56466 (13)	−0.37805 (7)	0.0361 (3)
F9B	0.79817 (14)	0.56898 (12)	0.88103 (6)	0.0293 (2)
N3A	0.49060 (18)	0.82060 (15)	0.14004 (9)	0.0215 (3)
N3B	0.66485 (18)	0.84586 (16)	0.37814 (9)	0.0216 (3)
N12A	0.8086 (2)	0.87201 (17)	0.19689 (10)	0.0257 (3)
N12B	0.3726 (2)	0.86969 (18)	0.31901 (9)	0.0247 (3)
O14A	0.11253 (16)	0.80146 (16)	0.11929 (8)	0.0305 (3)
O14B	1.02965 (16)	0.82851 (15)	0.39967 (8)	0.0294 (3)
S1A	0.68838 (5)	0.79416 (5)	0.01534 (3)	0.02509 (11)
S1B	0.42376 (5)	0.77503 (5)	0.49132 (2)	0.02230 (11)
H12A	0.786 (3)	0.873 (3)	0.2530 (17)	0.036 (6)*
H12B	0.911 (3)	0.856 (2)	0.1879 (15)	0.029 (5)*
H12C	0.265 (3)	0.853 (2)	0.3284 (15)	0.028 (5)*
H12D	0.392 (3)	0.865 (3)	0.2623 (19)	0.043 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C2A	0.0243 (7)	0.0251 (7)	0.0184 (7)	0.0090 (6)	0.0054 (6)	0.0024 (6)
C2B	0.0240 (7)	0.0248 (7)	0.0153 (7)	0.0081 (6)	0.0033 (5)	0.0016 (5)
C4A	0.0232 (7)	0.0257 (7)	0.0172 (7)	0.0078 (6)	0.0038 (6)	0.0026 (6)
C4B	0.0229 (7)	0.0248 (7)	0.0166 (7)	0.0064 (6)	0.0013 (6)	0.0018 (5)
C5A	0.0251 (7)	0.0254 (7)	0.0198 (7)	0.0094 (6)	0.0055 (6)	0.0040 (6)
C5B	0.0216 (7)	0.0242 (7)	0.0176 (7)	0.0066 (6)	0.0011 (6)	0.0000 (6)
C6A	0.0270 (7)	0.0293 (8)	0.0171 (7)	0.0137 (6)	0.0054 (6)	0.0032 (6)
C6B	0.0231 (7)	0.0272 (8)	0.0155 (7)	0.0107 (6)	0.0028 (5)	0.0017 (6)
C7A	0.0311 (8)	0.0274 (8)	0.0207 (8)	0.0110 (6)	0.0072 (6)	0.0020 (6)
C7B	0.0248 (7)	0.0266 (8)	0.0194 (7)	0.0084 (6)	0.0012 (6)	−0.0020 (6)
C8A	0.0363 (9)	0.0327 (8)	0.0183 (7)	0.0159 (7)	0.0092 (6)	0.0065 (6)
C8B	0.0288 (8)	0.0253 (7)	0.0205 (7)	0.0094 (6)	0.0058 (6)	0.0041 (6)
C9A	0.0321 (8)	0.0370 (9)	0.0157 (7)	0.0175 (7)	0.0007 (6)	−0.0003 (6)
C9B	0.0291 (8)	0.0319 (8)	0.0136 (7)	0.0153 (6)	0.0034 (6)	0.0037 (6)
C10A	0.0285 (8)	0.0303 (8)	0.0235 (8)	0.0099 (7)	0.0019 (6)	0.0014 (6)
C10B	0.0259 (8)	0.0323 (8)	0.0190 (7)	0.0095 (6)	−0.0011 (6)	0.0000 (6)
C11A	0.0277 (8)	0.0298 (8)	0.0197 (7)	0.0110 (6)	0.0046 (6)	0.0055 (6)
C11B	0.0236 (7)	0.0273 (8)	0.0202 (7)	0.0070 (6)	0.0020 (6)	0.0031 (6)
C13A	0.0220 (7)	0.0342 (8)	0.0200 (7)	0.0083 (6)	0.0024 (6)	0.0016 (6)
C13B	0.0223 (7)	0.0284 (8)	0.0215 (7)	0.0074 (6)	0.0019 (6)	0.0033 (6)
F9A	0.0448 (6)	0.0443 (6)	0.0173 (5)	0.0153 (5)	−0.0030 (4)	−0.0012 (4)
F9B	0.0375 (5)	0.0352 (5)	0.0157 (4)	0.0133 (4)	0.0017 (4)	0.0060 (4)
N3A	0.0219 (6)	0.0266 (6)	0.0168 (6)	0.0082 (5)	0.0039 (5)	0.0024 (5)
N3B	0.0221 (6)	0.0272 (6)	0.0157 (6)	0.0082 (5)	0.0027 (5)	0.0016 (5)
N12A	0.0219 (7)	0.0369 (8)	0.0191 (7)	0.0109 (6)	0.0032 (5)	−0.0011 (5)
N12B	0.0227 (7)	0.0383 (8)	0.0167 (6)	0.0140 (6)	0.0048 (5)	0.0051 (5)
O14A	0.0261 (6)	0.0447 (7)	0.0237 (6)	0.0140 (5)	0.0077 (5)	0.0019 (5)
O14B	0.0244 (6)	0.0378 (7)	0.0282 (6)	0.0109 (5)	0.0087 (5)	0.0069 (5)
S1A	0.0238 (2)	0.0362 (2)	0.01781 (19)	0.01206 (16)	0.00570 (14)	0.00075 (15)
S1B	0.02187 (19)	0.0323 (2)	0.01454 (18)	0.01058 (15)	0.00423 (13)	0.00355 (14)

Geometric parameters (Å, º) top

C2A—N3A	1.308 (2)	C7B—H7B	0.9500
C2A—N12A	1.343 (2)	C8A—C9A	1.375 (3)
C2A—S1A	1.7623 (16)	C8A—H8A	0.9500
C2B—N3B	1.309 (2)	C8B—C9B	1.377 (2)
C2B—N12B	1.344 (2)	C8B—H8B	0.9500
C2B—S1B	1.7585 (15)	C9A—F9A	1.3580 (18)
C4A—C5A	1.372 (2)	C9A—C10A	1.379 (2)
C4A—N3A	1.384 (2)	C9B—F9B	1.3626 (17)
C4A—C13A	1.455 (2)	C9B—C10B	1.375 (2)
C4B—C5B	1.374 (2)	C10A—C11A	1.391 (2)
C4B—N3B	1.388 (2)	C10A—H10A	0.9500
C4B—C13B	1.458 (2)	C10B—C11B	1.392 (2)
C5A—C6A	1.473 (2)	C10B—H10B	0.9500
C5A—S1A	1.7391 (16)	C11A—H11A	0.9500
C5B—C6B	1.477 (2)	C11B—H11B	0.9500
C5B—S1B	1.7342 (16)	C13A—O14A	1.224 (2)
C6A—C11A	1.397 (2)	C13A—H13A	0.9500
C6A—C7A	1.399 (2)	C13B—O14B	1.222 (2)
C6B—C11B	1.394 (2)	C13B—H13B	0.9500
C6B—C7B	1.398 (2)	N12A—H12A	0.87 (2)
C7A—C8A	1.387 (2)	N12A—H12B	0.86 (2)
C7A—H7A	0.9500	N12B—H12C	0.82 (2)
C7B—C8B	1.388 (2)	N12B—H12D	0.87 (3)

N3A—C2A—N12A	124.52 (14)	C7B—C8B—H8B	121.1
N3A—C2A—S1A	114.34 (12)	F9A—C9A—C8A	118.78 (15)
N12A—C2A—S1A	121.12 (12)	F9A—C9A—C10A	118.06 (16)
N3B—C2B—N12B	124.89 (14)	C8A—C9A—C10A	123.16 (15)
N3B—C2B—S1B	114.47 (11)	F9B—C9B—C10B	118.52 (14)
N12B—C2B—S1B	120.64 (12)	F9B—C9B—C8B	118.27 (14)
C5A—C4A—N3A	117.22 (14)	C10B—C9B—C8B	123.21 (14)
C5A—C4A—C13A	123.57 (14)	C9A—C10A—C11A	118.06 (16)
N3A—C4A—C13A	119.09 (13)	C9A—C10A—H10A	121.0
C5B—C4B—N3B	116.79 (14)	C11A—C10A—H10A	121.0
C5B—C4B—C13B	123.91 (14)	C9B—C10B—C11B	118.36 (15)
N3B—C4B—C13B	119.19 (13)	C9B—C10B—H10B	120.8
C4A—C5A—C6A	129.84 (15)	C11B—C10B—H10B	120.8
C4A—C5A—S1A	108.53 (12)	C10A—C11A—C6A	120.60 (15)
C6A—C5A—S1A	121.61 (12)	C10A—C11A—H11A	119.7
C4B—C5B—C6B	131.24 (14)	C6A—C11A—H11A	119.7
C4B—C5B—S1B	108.86 (11)	C10B—C11B—C6B	120.44 (15)
C6B—C5B—S1B	119.89 (11)	C10B—C11B—H11B	119.8
C11A—C6A—C7A	119.25 (15)	C6B—C11B—H11B	119.8
C11A—C6A—C5A	120.25 (14)	O14A—C13A—C4A	123.26 (15)
C7A—C6A—C5A	120.50 (15)	O14A—C13A—H13A	118.4
C11B—C6B—C7B	119.10 (14)	C4A—C13A—H13A	118.4
C11B—C6B—C5B	121.07 (14)	O14B—C13B—C4B	123.17 (15)
C7B—C6B—C5B	119.79 (14)	O14B—C13B—H13B	118.4
C8A—C7A—C6A	120.52 (16)	C4B—C13B—H13B	118.4
C8A—C7A—H7A	119.7	C2A—N3A—C4A	110.35 (13)
C6A—C7A—H7A	119.7	C2B—N3B—C4B	110.30 (13)
C8B—C7B—C6B	121.03 (15)	C2A—N12A—H12A	117.5 (16)
C8B—C7B—H7B	119.5	C2A—N12A—H12B	119.2 (14)
C6B—C7B—H7B	119.5	H12A—N12A—H12B	118 (2)
C9A—C8A—C7A	118.37 (15)	C2B—N12B—H12C	117.4 (15)
C9A—C8A—H8A	120.8	C2B—N12B—H12D	118.1 (17)
C7A—C8A—H8A	120.8	H12C—N12B—H12D	118 (2)
C9B—C8B—C7B	117.85 (15)	C5A—S1A—C2A	89.53 (7)
C9B—C8B—H8B	121.1	C5B—S1B—C2B	89.59 (7)

N3A—C4A—C5A—C6A	176.64 (15)	F9B—C9B—C10B—C11B	179.38 (14)
C13A—C4A—C5A—C6A	−7.5 (3)	C8B—C9B—C10B—C11B	−0.3 (3)
N3A—C4A—C5A—S1A	−1.54 (18)	C9A—C10A—C11A—C6A	−0.7 (2)
C13A—C4A—C5A—S1A	174.34 (13)	C7A—C6A—C11A—C10A	−0.6 (2)
N3B—C4B—C5B—C6B	179.83 (15)	C5A—C6A—C11A—C10A	178.85 (15)
C13B—C4B—C5B—C6B	3.8 (3)	C9B—C10B—C11B—C6B	0.3 (2)
N3B—C4B—C5B—S1B	0.85 (18)	C7B—C6B—C11B—C10B	0.3 (2)
C13B—C4B—C5B—S1B	−175.17 (13)	C5B—C6B—C11B—C10B	178.03 (15)
C4A—C5A—C6A—C11A	−60.0 (2)	C5A—C4A—C13A—O14A	−175.19 (17)
S1A—C5A—C6A—C11A	118.02 (15)	N3A—C4A—C13A—O14A	0.6 (3)
C4A—C5A—C6A—C7A	119.5 (2)	C5B—C4B—C13B—O14B	178.76 (16)
S1A—C5A—C6A—C7A	−62.50 (19)	N3B—C4B—C13B—O14B	2.8 (2)
C4B—C5B—C6B—C11B	58.8 (2)	N12A—C2A—N3A—C4A	179.29 (15)
S1B—C5B—C6B—C11B	−122.33 (15)	S1A—C2A—N3A—C4A	0.69 (17)
C4B—C5B—C6B—C7B	−123.49 (19)	C5A—C4A—N3A—C2A	0.6 (2)
S1B—C5B—C6B—C7B	55.40 (19)	C13A—C4A—N3A—C2A	−175.49 (14)
C11A—C6A—C7A—C8A	2.1 (2)	N12B—C2B—N3B—C4B	−179.90 (15)
C5A—C6A—C7A—C8A	−177.39 (15)	S1B—C2B—N3B—C4B	0.31 (17)
C11B—C6B—C7B—C8B	−0.9 (2)	C5B—C4B—N3B—C2B	−0.8 (2)
C5B—C6B—C7B—C8B	−178.70 (14)	C13B—C4B—N3B—C2B	175.45 (14)
C6A—C7A—C8A—C9A	−2.2 (2)	C4A—C5A—S1A—C2A	1.52 (12)
C6B—C7B—C8B—C9B	1.0 (2)	C6A—C5A—S1A—C2A	−176.85 (14)
C7A—C8A—C9A—F9A	−179.31 (15)	N3A—C2A—S1A—C5A	−1.32 (13)
C7A—C8A—C9A—C10A	0.8 (3)	N12A—C2A—S1A—C5A	−179.98 (14)
C7B—C8B—C9B—F9B	180.00 (14)	C4B—C5B—S1B—C2B	−0.53 (12)
C7B—C8B—C9B—C10B	−0.4 (2)	C6B—C5B—S1B—C2B	−179.65 (13)
F9A—C9A—C10A—C11A	−179.26 (14)	N3B—C2B—S1B—C5B	0.13 (13)
C8A—C9A—C10A—C11A	0.6 (3)	N12B—C2B—S1B—C5B	−179.67 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N12A—H12A···N3B	0.87 (2)	2.16 (3)	3.0121 (19)	167 (2)
N12A—H12B···O14Aⁱ	0.86 (2)	2.13 (2)	2.9596 (19)	160 (2)
N12B—H12C···O14Bⁱⁱ	0.82 (2)	2.16 (2)	2.9433 (19)	161 (2)
N12B—H12D···N3A	0.87 (3)	2.13 (3)	2.9778 (19)	164 (2)
C8A—H8A···S1Bⁱⁱⁱ	0.95	2.91	3.6376 (16)	134
C8B—H8B···N3A^iv	0.95	2.68	3.521 (2)	149
C13B—H13B···F9A^v	0.95	2.60	3.4911 (19)	157
C7B—H7B···Cg3^iv	0.95	2.75	3.4117 (17)	127

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

2-Amino-5-(4-chlorophenyl)-1,3-thiazole-4-carbaldehyde (II) top

Crystal data top

C₁₀H₇ClN₂OS	F(000) = 976
M_r = 238.69	D_x = 1.556 Mg m⁻³
Monoclinic, I2/a	Cu Kα radiation, λ = 1.54184 Å
a = 13.9857 (2) Å	Cell parameters from 9428 reflections
b = 9.8459 (1) Å	θ = 5.4–79.9°
c = 15.3349 (2) Å	µ = 5.01 mm⁻¹
β = 105.170 (1)°	T = 100 K
V = 2038.06 (5) Å³	Prism, yellow
Z = 8	0.53 × 0.38 × 0.30 mm

Data collection top

XtaLAB Synergy, Dualflex, HyPix diffractometer	2220 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	2165 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.043
Detector resolution: 10.0000 pixels mm^-1	θ_max = 80.3°, θ_min = 5.4°
ω scans	h = −17→17
Absorption correction: gaussian (CrysAlisPr; (Rigaku OD, 2025)	k = −10→12
T_min = 0.169, T_max = 0.859	l = −19→19
13963 measured 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)] = 0.036	Hydrogen site location: mixed
wR(F²) = 0.094	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0543P)² + 2.2643P] where P = (F_o² + 2F_c²)/3
2220 reflections	(Δ/σ)_max = 0.001
144 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.37 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
C2	0.59720 (12)	0.44375 (16)	0.12413 (11)	0.0197 (3)
C4	0.50163 (12)	0.54350 (17)	0.19941 (10)	0.0194 (3)
C5	0.57830 (12)	0.51273 (16)	0.27300 (10)	0.0194 (3)
C6	0.59306 (12)	0.55034 (17)	0.36882 (11)	0.0202 (3)
C7	0.61451 (13)	0.45314 (18)	0.43726 (11)	0.0227 (3)
H7	0.618549	0.360040	0.422360	0.027*
C8	0.63007 (13)	0.49141 (18)	0.52726 (11)	0.0237 (3)
H8	0.643953	0.425002	0.573823	0.028*
C9	0.62502 (13)	0.62773 (18)	0.54796 (11)	0.0230 (3)
C10	0.60396 (13)	0.72642 (18)	0.48120 (12)	0.0258 (4)
H10	0.600421	0.819419	0.496565	0.031*
C11	0.58812 (13)	0.68741 (18)	0.39163 (12)	0.0242 (4)
H11	0.573797	0.754261	0.345349	0.029*
C13	0.41003 (13)	0.60683 (17)	0.20523 (11)	0.0211 (3)
H13	0.401977	0.627562	0.263401	0.025*
Cl9	0.64554 (3)	0.67747 (4)	0.66029 (3)	0.02945 (14)
N3	0.51246 (10)	0.50539 (14)	0.11549 (9)	0.0193 (3)
N12	0.62848 (12)	0.39102 (17)	0.05542 (10)	0.0240 (3)
O14	0.34230 (9)	0.63509 (13)	0.13888 (8)	0.0242 (3)
S1	0.66956 (3)	0.42813 (4)	0.23650 (2)	0.02012 (13)
H12A	0.597 (2)	0.418 (3)	0.0043 (19)	0.033 (6)*
H12B	0.687 (2)	0.376 (2)	0.0650 (17)	0.028 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C2	0.0236 (8)	0.0222 (7)	0.0133 (7)	−0.0032 (6)	0.0052 (6)	−0.0007 (6)
C4	0.0238 (8)	0.0223 (7)	0.0128 (7)	−0.0026 (6)	0.0058 (6)	−0.0007 (6)
C5	0.0224 (7)	0.0225 (7)	0.0143 (7)	0.0001 (6)	0.0065 (6)	0.0005 (6)
C6	0.0216 (7)	0.0264 (8)	0.0131 (7)	0.0009 (6)	0.0051 (6)	−0.0016 (6)
C7	0.0261 (8)	0.0248 (8)	0.0167 (8)	0.0035 (6)	0.0050 (6)	−0.0014 (6)
C8	0.0286 (8)	0.0278 (8)	0.0138 (7)	0.0052 (6)	0.0042 (6)	0.0022 (6)
C9	0.0252 (8)	0.0310 (9)	0.0123 (7)	0.0048 (6)	0.0040 (6)	−0.0034 (6)
C10	0.0333 (9)	0.0244 (8)	0.0185 (8)	0.0029 (7)	0.0048 (7)	−0.0024 (6)
C11	0.0308 (9)	0.0249 (8)	0.0157 (8)	0.0019 (6)	0.0043 (6)	0.0020 (6)
C13	0.0266 (8)	0.0226 (7)	0.0152 (7)	−0.0011 (6)	0.0075 (6)	0.0009 (6)
Cl9	0.0417 (3)	0.0328 (2)	0.0120 (2)	0.00928 (17)	0.00381 (17)	−0.00327 (14)
N3	0.0225 (6)	0.0242 (6)	0.0118 (6)	−0.0025 (5)	0.0057 (5)	−0.0015 (5)
N12	0.0228 (7)	0.0350 (8)	0.0141 (7)	0.0030 (6)	0.0047 (6)	−0.0028 (6)
O14	0.0226 (6)	0.0308 (6)	0.0186 (6)	0.0005 (5)	0.0040 (5)	0.0010 (5)
S1	0.0216 (2)	0.0264 (2)	0.0123 (2)	0.00179 (13)	0.00437 (15)	−0.00110 (13)

Geometric parameters (Å, º) top

C2—N3	1.307 (2)	C8—C9	1.385 (3)
C2—N12	1.346 (2)	C8—H8	0.9500
C2—S1	1.7620 (16)	C9—C10	1.386 (3)
C4—C5	1.372 (2)	C9—Cl9	1.7410 (16)
C4—N3	1.386 (2)	C10—C11	1.387 (2)
C4—C13	1.448 (2)	C10—H10	0.9500
C5—C6	1.477 (2)	C11—H11	0.9500
C5—S1	1.7349 (16)	C13—O14	1.227 (2)
C6—C7	1.394 (2)	C13—H13	0.9500
C6—C11	1.400 (2)	N12—H12A	0.84 (3)
C7—C8	1.392 (2)	N12—H12B	0.81 (3)
C7—H7	0.9500

N3—C2—N12	124.85 (15)	C8—C9—C10	121.58 (15)
N3—C2—S1	114.41 (12)	C8—C9—Cl9	119.62 (13)
N12—C2—S1	120.71 (13)	C10—C9—Cl9	118.80 (14)
C5—C4—N3	116.88 (15)	C9—C10—C11	119.03 (16)
C5—C4—C13	123.91 (15)	C9—C10—H10	120.5
N3—C4—C13	119.15 (14)	C11—C10—H10	120.5
C4—C5—C6	129.71 (15)	C10—C11—C6	120.57 (16)
C4—C5—S1	108.86 (12)	C10—C11—H11	119.7
C6—C5—S1	121.23 (12)	C6—C11—H11	119.7
C7—C6—C11	119.25 (15)	O14—C13—C4	123.35 (15)
C7—C6—C5	121.58 (15)	O14—C13—H13	118.3
C11—C6—C5	119.15 (15)	C4—C13—H13	118.3
C8—C7—C6	120.52 (16)	C2—N3—C4	110.36 (14)
C8—C7—H7	119.7	C2—N12—H12A	114.3 (18)
C6—C7—H7	119.7	C2—N12—H12B	116.8 (18)
C9—C8—C7	119.04 (16)	H12A—N12—H12B	119 (2)
C9—C8—H8	120.5	C5—S1—C2	89.48 (8)
C7—C8—H8	120.5

N3—C4—C5—C6	173.71 (16)	Cl9—C9—C10—C11	179.63 (14)
C13—C4—C5—C6	−9.2 (3)	C9—C10—C11—C6	0.2 (3)
N3—C4—C5—S1	−1.08 (18)	C7—C6—C11—C10	−0.3 (3)
C13—C4—C5—S1	176.03 (13)	C5—C6—C11—C10	−178.47 (16)
C4—C5—C6—C7	128.1 (2)	C5—C4—C13—O14	179.28 (16)
S1—C5—C6—C7	−57.7 (2)	N3—C4—C13—O14	−3.7 (3)
C4—C5—C6—C11	−53.7 (3)	N12—C2—N3—C4	178.02 (16)
S1—C5—C6—C11	120.52 (16)	S1—C2—N3—C4	0.09 (18)
C11—C6—C7—C8	0.5 (3)	C5—C4—N3—C2	0.7 (2)
C5—C6—C7—C8	178.71 (16)	C13—C4—N3—C2	−176.60 (15)
C6—C7—C8—C9	−0.7 (3)	C4—C5—S1—C2	0.89 (12)
C7—C8—C9—C10	0.6 (3)	C6—C5—S1—C2	−174.43 (14)
C7—C8—C9—Cl9	−179.35 (13)	N3—C2—S1—C5	−0.59 (13)
C8—C9—C10—C11	−0.3 (3)	N12—C2—S1—C5	−178.61 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N12—H12A···N3ⁱ	0.84 (3)	2.19 (3)	3.015 (2)	167 (2)
N12—H12A···O14ⁱ	0.84 (3)	2.61 (3)	3.1222 (19)	121 (2)
N12—H12B···O14ⁱⁱ	0.81 (3)	2.18 (3)	2.940 (2)	159 (2)
C9—Cl9···Cg1ⁱⁱⁱ	1.74 (1)	3.53 (1)	4.5317 (19)	114 (1)

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

Acknowledgements

This work has been supported by the Kosygin State University of Russia, N. D. Zelinsky Institute of Organic Chemistry, Russian State Agrarian University–Moscow Timiryazev Agricultural Academy, Erciyes University (Türkiye), Baku State University (Azerbaijan), and Azerbaijan Medical University. The authors' contributions are as follows. Conceptualization, FIG, MA, and ANB; synthesis, KAA and SMG; X-ray analysis, AMP and FSA; writing (review and editing of the manuscript), FIG, KIH, and MA; funding acquisition, FSA and KIH; supervision, FIG, MA, and ANB.

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

Consistent supra­molecular motifs and different local symmetries in the structures of 2-amino-5-(4-fluoro­phen­yl)-1,3-thia­zole-4-carbaldehyde and 2-amino-5-(4-chloro­phen­yl)-1,3-thia­zole-4-carbaldehyde

1. Chemical context

2. Structural commentary

3. Supra­molecular features and Hirshfeld surface analyses

4. Database survey

5. Synthesis and crystallization

6. Refinement

Supporting information

Acknowledgements

References

research communications

Consistent supramolecular motifs and different local symmetries in the structures of 2-amino-5-(4-fluorophenyl)-1,3-thiazole-4-carbaldehyde and 2-amino-5-(4-chlorophenyl)-1,3-thiazole-4-carbaldehyde

3. Supramolecular features and Hirshfeld surface analyses