The title compounds have different local symmetries but a consistent supramolecular motif of zigzag supramolecular ribbons propagating along the [100] direction linked by N—H⋯N and N—H⋯O hydrogen bonds. Various weak interactions consolidate both structures.
Keywords: crystal structure; 1,3-thiazole ring; haloketones; halooxiranes
Abstract
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)].
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
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 
(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 
(14) motifs between them (Fig. 3 ▸). Additionally, the molecules in these ribbons form 
(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⋯N3Aiv | 0.95 | 2.68 | 3.521 (2) | 149 |
| C13B—H13B⋯F9Av | 0.95 | 2.60 | 3.4911 (19) | 157 |
| C7B—H7B⋯Cg3iv | 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 [(8)(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 
(8)
(5)(8)(5)(8) motifs (Fig. 4 ▸). In addition, π–π [Cg2⋯Cg2a = 3.8099 (11) Å, slippage = 1.011 Å; symmetry code (a) 
− 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) 
; (iii) 
.
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 [(8)(5)(8)(5)(8)]n motifs. Symmetry codes: (i) −x + 1, −y + 1, −z; (ii) x + 
, −y + 1, z; (iii) x + , −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 dnorm 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 dnorm 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 dnorm.
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 (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 (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
|
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 ▸) |
| Tmin, Tmax | 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 |
| Δρmax, Δρmin (e Å−3) | 0.30, −0.32 | 0.37, −0.37 |
Supplementary Material
Crystal structure: contains datablock(s) I, II. DOI: 10.1107/S2056989025010667/hb8159sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989025010667/hb8159Isup4.hkl
Structure factors: contains datablock(s) II. DOI: 10.1107/S2056989025010667/hb8159IIsup5.hkl
Supporting information file. DOI: 10.1107/S2056989025010667/hb8159Isup4.cml
Supporting information file. DOI: 10.1107/S2056989025010667/hb8159IIsup5.cml
Supplementary Material. DOI: 10.1107/S2056989025010667/hb8159sup6.pdf
Additional supporting information: crystallographic information; 3D view; checkCIF report
Acknowledgments
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.
supplementary crystallographic information
2-Amino-5-(4-fluorophenyl)-1,3-thiazole-4-carbaldehyde (I). Crystal data
| C10H7FN2OS | Z = 4 |
| Mr = 222.24 | F(000) = 456 |
| Triclinic, P1 | Dx = 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 |
2-Amino-5-(4-fluorophenyl)-1,3-thiazole-4-carbaldehyde (I). Data collection
| 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 | Rint = 0.047 |
| Detector resolution: 10.0000 pixels mm-1 | θmax = 79.8°, θmin = 3.0° |
| ω scans | h = −9→9 |
| Absorption correction: gaussian (CrysAlisPro; Rigaku OD, 2025) | k = −11→11 |
| Tmin = 0.482, Tmax = 0.642 | l = −18→18 |
| 25299 measured reflections |
2-Amino-5-(4-fluorophenyl)-1,3-thiazole-4-carbaldehyde (I). Refinement
| 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(Fo2) + (0.0488P)2 + 0.4701P] where P = (Fo2 + 2Fc2)/3 |
| 4097 reflections | (Δ/σ)max = 0.001 |
| 287 parameters | Δρmax = 0.30 e Å−3 |
| 0 restraints | Δρmin = −0.32 e Å−3 |
2-Amino-5-(4-fluorophenyl)-1,3-thiazole-4-carbaldehyde (I). Special details
| 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. |
2-Amino-5-(4-fluorophenyl)-1,3-thiazole-4-carbaldehyde (I). Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| 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)* |
2-Amino-5-(4-fluorophenyl)-1,3-thiazole-4-carbaldehyde (I). Atomic displacement parameters (Å2)
| 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) |
2-Amino-5-(4-fluorophenyl)-1,3-thiazole-4-carbaldehyde (I). Geometric parameters (Å, º)
| 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) |
2-Amino-5-(4-fluorophenyl)-1,3-thiazole-4-carbaldehyde (I). Hydrogen-bond geometry (Å, º)
| 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···N3Aiv | 0.95 | 2.68 | 3.521 (2) | 149 |
| C13B—H13B···F9Av | 0.95 | 2.60 | 3.4911 (19) | 157 |
| C7B—H7B···Cg3iv | 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). Crystal data
| C10H7ClN2OS | F(000) = 976 |
| Mr = 238.69 | Dx = 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 |
2-Amino-5-(4-chlorophenyl)-1,3-thiazole-4-carbaldehyde (II). Data collection
| 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 | Rint = 0.043 |
| Detector resolution: 10.0000 pixels mm-1 | θmax = 80.3°, θmin = 5.4° |
| ω scans | h = −17→17 |
| Absorption correction: gaussian (CrysAlisPr; (Rigaku OD, 2025) | k = −10→12 |
| Tmin = 0.169, Tmax = 0.859 | l = −19→19 |
| 13963 measured reflections |
2-Amino-5-(4-chlorophenyl)-1,3-thiazole-4-carbaldehyde (II). Refinement
| 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(Fo2) + (0.0543P)2 + 2.2643P] where P = (Fo2 + 2Fc2)/3 |
| 2220 reflections | (Δ/σ)max = 0.001 |
| 144 parameters | Δρmax = 0.37 e Å−3 |
| 0 restraints | Δρmin = −0.37 e Å−3 |
2-Amino-5-(4-chlorophenyl)-1,3-thiazole-4-carbaldehyde (II). Special details
| 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. |
2-Amino-5-(4-chlorophenyl)-1,3-thiazole-4-carbaldehyde (II). Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| 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)* |
2-Amino-5-(4-chlorophenyl)-1,3-thiazole-4-carbaldehyde (II). Atomic displacement parameters (Å2)
| 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) |
2-Amino-5-(4-chlorophenyl)-1,3-thiazole-4-carbaldehyde (II). Geometric parameters (Å, º)
| 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) |
2-Amino-5-(4-chlorophenyl)-1,3-thiazole-4-carbaldehyde (II). Hydrogen-bond geometry (Å, º)
| 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.
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) I, II. DOI: 10.1107/S2056989025010667/hb8159sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989025010667/hb8159Isup4.hkl
Structure factors: contains datablock(s) II. DOI: 10.1107/S2056989025010667/hb8159IIsup5.hkl
Supporting information file. DOI: 10.1107/S2056989025010667/hb8159Isup4.cml
Supporting information file. DOI: 10.1107/S2056989025010667/hb8159IIsup5.cml
Supplementary Material. DOI: 10.1107/S2056989025010667/hb8159sup6.pdf
Additional supporting information: crystallographic information; 3D view; checkCIF report