Synthesis and spectroscopic and structural characterization of three new 2-methyl-4-styryl­quinolines formed using Friedländer reactions between (2-amino­phen­yl)chalcones and acetone

Vera, D.R.; Mantilla, J.P.; Palma, A.; Cobo, J.; Glidewell, C.

doi:10.1107/S2053229622008634

research papers

STRUCTURAL
CHEMISTRY

ISSN: 2053-2296

Volume 78| Part 10| October 2022| Pages 524-530

https://doi.org/10.1107/S2053229622008634

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Synthesis and spectroscopic and structural characterization of three new 2-methyl-4-styrylquinolines formed using Friedländer reactions between (2-aminophenyl)chalcones and acetone

Diana Rocío Vera,^a Juan P. Mantilla,^a Alirio Palma,^a Justo Cobo ^b and Christopher Glidewell ^c ^*

^aLaboratorio de Síntesis Orgánica, Escuela de Química, Universidad Industrial de Santander, AA 678, Bucaramanga, Colombia, ^bDepartamento de Química Inorgánica y Orgánica, Universidad de Jaén, 23071 Jaén, Spain, and ^cSchool of Chemistry, University of St Andrews, St Andrews, Fife KY16 9ST, United Kingdom
^*Correspondence e-mail: cg@st-andrews.ac.uk

Edited by A. R. Kennedy, University of Strathclyde, United Kingdom (Received 11 July 2022; accepted 29 August 2022; online 5 September 2022)

Three new 2-methyl-4-styrylquinoline derivatives have been synthesized in high yields using Friedländer reactions between chalcones [1-(2-aminophenyl)-3-arylprop-2-en-1-ones] and acetone, and characterized using IR, ¹H and ¹³C NMR spectroscopy, and mass spectrometry, and by crystal structure analysis. In (E)-4-(4-fluorostyryl)-2-methylquinoline, C₁₈H₁₄FN, (I), the molecules are joined into cyclic centrosymmetric dimers by C—H⋯N hydrogen bonds and these dimers are linked into sheets by π–π stacking interactions. The molecules of (E)-2-methyl-4-[4-(trifluoromethyl)styryl]quinoline, C₁₉H₁₄F₃N, (II), are linked into cyclic centrosymmetric dimers by C—H⋯π hydrogen bonds and these dimers are linked into chains by a single π–π stacking interaction. There are no significant hydrogen bonds in the structure of (E)-4-(2,6-dichlorostyryl)-2-methylquinoline, C₁₈H₁₃Cl₂N, (III), but molecules related by translation along [010] form stacks with an intermolecular spacing of only 3.8628 (2) Å. Comparisons are made with the structures of some related compounds.

Keywords: synthesis; quinoline; Friedlander reaction; NMR spectroscopy; crystal structure; molecular conformation; hydrogen bonding; supramolecular assembly.

CCDC references: 2204061; 2204060; 2204059

1. Introduction

The quinoline nucleus constitutes a privileged scaffold because of the wide spectrum of promising biological activity exhibited by its derivatives (Kumar et al., 2009 ). Among quinoline derivatives, 2-styrylquinolines have been studied extensively, mainly because of their potential as inhibitors of HIV-1 integrase (Leonard & Roy, 2008 ; Mahajan et al., 2018 ; Mousnier et al., 2004 ) and as antimicrobial (Kamal et al., 2015 ), antifungal (Cieslik et al., 2012 ) and anticancer agents (Mrozek-Wilczkiewicz et al., 2015 , 2019 ).

Accordingly, considerable efforts have been made in the development of effective methods for accessing new compounds containing the styrylquinoline scaffold (Musiol, 2020 ). Unlike 2-styrylquinolines, the 4-styrylquinoline regioisomers have been studied much less, with few published reports related to their synthesis and biological evaluation, which is probably due, at least in part, to a lack of generally applicable methodologies for their synthesis. In general, the published syntheses of 4-styrylquinolines have involved Heck coupling between 4-haloquinolines and different aryl–vinyl compounds (Omar & Hormi, 2009 ), and Knoevenagel-type condensation reactions between 4-methylquinolines and aromatic aldehydes using expensive and toxic heavy-metal catalysts (Jamal et al., 2016 ) or microwave irradiation (Lee et al., 2009 ). The use of palladium catalysts in the cross-coupling reaction between 4-chloroquinolines and alkenyltrifluoroborates under harsh reaction conditions has also been reported (Alacid & Nájera, 2009 ). Nonetheless, there still remains a need for alternative approaches for the construction of 4-styrylquinolines starting from readily accessible materials and characterized by high atom efficiency and low cost.

In this context, and as part of an ongoing program exploring the rational use of synthetically available 1-(2-aminophenyl)-3-arylprop-2-en-1-ones (Meléndez et al., 2020 ) as appropriate precursors for the synthesis of novel quinoline derivatives, we have recently described a simple and efficient one-pot synthetic approach based on the Friedländer reaction to obtain polysubstituted 2-methyl-4-styrylquinolines starting from these simple precursors and different 1,3-dicarbonyl compounds (Meléndez et al., 2020).

To expand further both the synthetic utility of 1-(2-aminophenyl)-3-arylprop-2-en-1-ones and the flexibility of our approach, we report here the synthesis, characterization and molecular and supramolecular structures of a matched set of three closely-related quinoline derivatives, namely, (E)-4-(4-fluorostyryl)-2-methylquinoline, (I), (E)-2-methyl-4-[4-(trifluoromethyl)styryl]quinoline, (II), and (E)-4-(2,6-dichlorostyryl)-2-methylquinoline, (III) (Scheme 1 and Figs. 1–3 ), which differ only in the nature of the substituents at the C4 and C2/C6 positions on the benzene ring of the styryl fragment. Using our synthetic approach (Meléndez et al., 2020), (E)-1-(2-aminophenyl)-3-arylprop-2-en-1-ones of type (A) (Scheme 1) were subjected to Friedlander annulation with an excess of acetone in glacial acetic acid at 373 K, to provide the products (I)–(III) with yields in the range 77–94% (Scheme 1). These new 2-methylquinoline derivatives are intended for use as key precursors in the further development of more complex molecules of possible biological value, such as the bis-styrylquinolines (IV) (Scheme 2), (4-styrylquinolin-2-yl)chalcones of the type (V) and the molecular hybrids of types (VI) and (VII).

Figure 1
The molecular structure of compound (I)

, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.

Figure 2
The molecular structure of compound (II)

, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.

Figure 3
The molecular structure of compound (III)

, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.

2. Experimental

2.1. Synthesis and crystallization

For the synthesis of compounds (I)–(III), a mixture of the appropriate 1-(2-aminophenyl)-3-arylprop-2-en-1-ones (A) (Meléndez et al., 2020; see Scheme 1) (1.0 mmol) and acetone (12.0 mmol) in glacial acetic acid (3 ml) was stirred magnetically and heated at 353 K until the reactions were complete, as judged by the complete consumption of (A) (as monitored by thin-layer chromatography, TLC); the reaction times for completion were 15 h for (I), 19 h for (II) and 14 h for (III). Each reaction mixture was then neutralized with a saturated aqueous sodium carbonate solution and extracted with ethyl acetate (3 × 50 ml). The combined organic layers were washed with water and dried over anhydrous sodium sulfate, and the solvent was then removed under reduced pressure. In each case, the resulting crude product was purified by flash chromatography on silica-gel using hexane–ethyl acetate mixtures as eluent (compositions ranged from 7:1 to 2:1 v/v) to give the required solid compounds (I)–(III). Crystallization from hexane–ethyl acetate (10:1 v/v) at ambient temperature and in the presence of air gave crystals suitable for single-crystal X-ray diffraction; these were yellow for (I) and (III), and colourless for (II).

Compound (I): yield 0.21g (84%), m.p. 395–397 K, R_f = 0.28 (16.6% ethyl acetate–hexane). FT–IR (ATR, cm⁻¹): 1632 (C=N), 1598 (C=C_vinyl), 1587 (C=C_arom), 1506 (C=C_arom), 965 (=C—H_trans). NMR (CDCl₃): δ(¹H) 8.13 (dd, J = 8.4, 1.4 Hz, 1H, H5), 8.05 (dd, J = 8.4, 1.6 Hz, 1H, H8), 7.69 (ddd, J = 8.4, 6.9, 1.4 Hz, 1H, H7), 7.68 (d, J = 16.1 Hz, 1H, H_A—C=), 7.56–7.61 (m, 2H, H2′, H6′), 7.52 (ddd, J = 8.3, 6.9, 1.4 Hz, 1H, H6), 7.47 (s, 1H, H3), 7.27 (d, J = 16.1 Hz, 1H, =CH_B), 7.09–7.14 (m, 2H, H3′, H5′), 2.77 (s, 3H, 2-CH₃); δ(¹³C) 163.0 (d, J = 248.9 Hz, C4′), 158.7 (C2), 148.4 (C8a), 142.8 (C4), 133.6 (=CH_B), 132.9 (d, J = 3.6 Hz, C1′), 129.4 (C8), 129.3 (C7), 128.7 (d, J = 8.1 Hz, C2′, C6′), 125.7 (C6), 124.7 (C4a), 123.2 (C5), 122.9 (d, J = 2.3 Hz, H_AC=), 117.9 (C3), 115.9 (d, J = 21.9 Hz, C3′, C5′), 25.4 (2-CH₃). HRMS (ESI⁺) m/z found for [M + H]⁺ 264.1181, C₁₈H₁₄FN requires 263.11

Compound (II): yield (77%); m.p. 391–392 K, R_f = 0.34 (50% ethyl acetate–hexane). FT–IR (ATR, cm⁻¹): 1620 (C=N), 1587 (C=C_vinyl), 1505 (C=C_arom), 1408 (C=C_arom), 964 (=C—H_trans). NMR (CDCl₃): δ(¹H) 8.13 (dd, J = 8.3, 1.4 Hz, 1H, H5), 8.06 (dd, J = 8.4, 1.5, Hz, 1H, H8), 7.86 (d, J = 16.1 Hz, 1H, H_A—C=), 7.72 (ddd, J = 8.3, 6.9, 1.4 Hz, 1H, H7), 7.72 (d, J = 8.5 Hz, 2H, H2′, H6′), 7.68 (d, J = 8.5 Hz, 2H, H3′, H5′), 7.54 (ddd, J = 8.3, 6.8, 1.3 Hz, 1H, H6), 7.50 (d, J = 0.7 Hz, 1H, H3), 7.32 (d, J = 16.1 Hz, 1H, =CH_B), 2.79 (s, 3H, 2-CH₃); δ (¹³C) 158.8 (C2), 148.5 (C8a), 142.3 (C4), 140.0 (C1′), 133.2 (=CH_B), 130.3 (d, J = 32.4 Hz, C4′), 129.5 (C7), 129.4 (C8), 127.2 (C2′, C6′, C3′, C5′), 125.9 (q, J = 3.7 Hz, 4-CF₃), 125.4 (C6), 124.7 (C4a), 123.1 (C5), 122.7 (H_A—C=), 118.2 (C3), 25.4 (2-CH₃). HRMS (ESI⁺) m/z found for [M + H]⁺ 314.115, C₁₉H₁₄F₃N requires 313.1078.

Compound (III): yield 0.25 g (94%), m.p. 410-412 K, R_f = 0.31 (12.5% ethyl acetate–hexane). FT–IR (ATR, cm⁻¹): 1629 (C=N), 1593 (C=C_vinyl), 1554 (C=C_arom), 1505 (C=C_arom), 959 (=C—H_trans). NMR (CDCl₃): δ(¹H) 8.10 (dd, J = 8.5, 1.4 Hz, 1H, H5), 8.06 (dd, J = 8.5, 1.4 Hz, 1H, H8), 7.85 (dd, J = 16.5, 0.87 Hz, 1H, H_A—C=), 7.70 (ddd, J = 8.4, 6.9, 1.4 Hz, 1H, H7), 7.53 (ddd, J = 8.4, 6.9, 1.3 Hz, 1H, H6), 7.53 (s, 1H, H3), 7.41 (d, J = 8.0 Hz, 2H, H3′, H5′), 7.18 (dd, J = 8.4, 7.7 Hz, 1H, H4′), 7.28 (d, J = 16.5 Hz, 1H, =CH_B), 2.80 (s, 3H, 2-CH₃). δ (¹³C) 158.8 (C2), 148.4 (C8a), 142.2 (C4), 137.2 (C1′), 134.7 (C2′, C6′), 133.8 (C3′), 132.4 (H_AC=), 130.9 (=CH_B), 130.1 (C4′), 129.3 (C7), 129.4 (C8), 127.4 (C5′), 125.9 (C6), 124.8 (C4a), 123.6 (C5), 118.5 (C3), 25.5 (2-CH₃). HRMS (ESI⁺) m/z found for [M + H]⁺ 314.0500, C₁₈H₁₃Cl₂N requires 313.0425.

2.2. Refinement

Crystal data, data collection and refinement details are summarized in Table 1. A small number of bad outlier reflections [ $[\overline{6}]$ 36 for (I), 204 and $[\overline{3}]$ 36 for (II), and 16,0,0 and 339 for (III)] were omitted from the data sets. All H atoms were located in difference maps and then treated as riding atoms in geometrically idealized positions, with C—H distances of 0.95 (alkenic and aromatic) and 0.98 Å (CH₃), and with U_iso(H) = kU_eq(C), where k = 1.5 for the methyl groups, which were permitted to rotate but not to tilt, and 1.2 for all other H atoms.

Table 1
Experimental details

Experiments were carried out at 100 K with Mo Kα radiation using a Bruker D8 Venture diffractometer. Absorption was corrected for by multi-scan methods (SADABS; Bruker, 2016 ). H-atom parameters were constrained.

	(I)	(II)	(III)
Crystal data
Chemical formula	C₁₈H₁₄FN	C₁₉H₁₄F₃N	C₁₈H₁₃Cl₂N
M_r	263.30	313.31	314.19
Crystal system, space group	Monoclinic, P2₁/c	Monoclinic, C2/c	Monoclinic, C2/c
a, b, c (Å)	13.5921 (7), 12.7103 (6), 7.6215 (3)	17.2696 (10), 10.8096 (7), 16.1495 (8)	30.5651 (15), 3.8629 (2), 25.5357 (13)
β (°)	103.133 (2)	91.440 (2)	110.497 (2)
V (Å³)	1282.25 (10)	3013.8 (3)	2824.1 (2)
Z	4	8	8
μ (mm⁻¹)	0.09	0.11	0.45
Crystal size (mm)	0.20 × 0.08 × 0.07	0.16 × 0.14 × 0.12	0.20 × 0.10 × 0.06

Data collection
T_min, T_max	0.934, 0.994	0.888, 0.987	0.897, 0.973
No. of measured, independent and observed [I > 2σ(I)] reflections	38068, 2949, 2342	46287, 3750, 2921	28110, 3208, 2930
R_int	0.079	0.085	0.042
(sin θ/λ)_max (Å⁻¹)	0.650	0.667	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.100, 1.05	0.047, 0.121, 1.03	0.031, 0.079, 1.07
No. of reflections	2949	3750	3208
No. of parameters	182	209	191
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.22	0.33, −0.30	0.33, −0.26
Computer programs: APEX3 (Bruker, 2018 ), SAINT (Bruker, 2017 ), SHELXT2014 (Sheldrick, 2015a ), SHELXL2014 (Sheldrick, 2015b ) and PLATON (Spek, 2020 ).

3. Results and discussion

All compounds were fully characterized by standard spectroscopic and analytical methods. In the IR spectra of (I)–(III), the absence of any N—H stretching bands around 3275–3285 cm⁻¹, which are characteristic in the spectra of (2-aminophenyl)chalcone precurors, was used for monitoring the formation of the quinoline ring. The formation of the 4-styrylquinoline scaffold was confirmed by a detailed analysis of the ¹H, ¹³C and 2D NMR spectra, which showed no signals arising from the H atoms of the amino group; neither were there any signals from the carbonyl groups which had been present in the precursor chalcones. Instead, the ¹³C spectra of the products contained signals from a new C_aryl—H unit (C-3) in the range δ 117.9–118.5, and two new quaternary aromatic C atoms at δ 158.7–158.8 (C-2) and 142.2–142.8 (C-4). As in the spectra of the precursor chalcones, the ¹H spectra of products (I)–(III) contained signals from the trans vinylic protons –CH_A=CH_B–, appearing as two doublets (see Section 2.1). Finally, definitive confirmation of the molecular constitutions and the regio- and stereochemistry for compounds (I)–(III) was established by means of single-crystal X-ray diffraction, and thus we report here also the molecular and supramolecular structures for all three examples (Figs. 1–3 ).

These new 2-methylquinoline derivatives (I)–(III) are intended for use as key precursors in the further development of more complex molecules of possible biological value, such as the bis-styrylquinolines (IV) (Scheme 2), (4-styrylquinolin-2-yl)chalcones of the type (V), and the molecular hybrids of types (VI) and (VII), and the work reported here can be regarded as a continuation of an earlier crystallographic study which reported the structures of 2-methyl-4-styrylquinolines having either acetyl or carboethoxy functionalities at position C3 (Rodríguez et al., 2020 ).

The molecules of compounds (I)–(III) exhibit no internal symmetry, as indicated by the key torsion angles (Table 2). They are thus not superimposable upon their mirror images and hence they are all conformationally chiral (Moss, 1996 ; Flack & Bernardinelli, 1999 ). The space groups (Table 1) confirm that the crystals of each compound contain equal numbers of the two conformational enantiomers; for each compound, the reference molecule was selected as one having a positive sign for the torsion angle C3—C4—C41—C42 (Table 2). Only in compound (II) is the styryl fragment involved in direction-specific intermolecular interactions, as discussed below, and hence there appears to be no simple interpretation of the conformational differences in compounds (I)–(III), other than to note that the barriers to rotation about the C—C single bonds are generally quite low, typically a few kJ mol⁻¹ (Alkorta & Elguero, 1998 ).

Table 2
Selected torsion angles (°) for compounds (I)–(III)

Parameter	(I)	(II)	(III)
C3—C4—C41—C42	38.8 (2)	28.1 (2)	39.5 (2)
C41—C42—C421—C422	−174.47 (15)	−175.59 (15)	139.58 (15)

The supramolecular assembly in compounds (I)–(III) is very simple (Table 3). There is a single hydrogen bond in the structure of (I). In the structure of (II), there is a C—H⋯π(arene) hydrogen bond, but for the intermolecular C—H⋯N contact, the H⋯N distance exceeds the sum, 2.70 Å, of the van der Waals radii for these atoms (Rowland & Taylor, 1996 ); hence, this is just a normal intermolecular contact with no associated attractive interaction which could be regarded as structurally significant. The C—H⋯N contact in compound (III) involves a methyl group (Table 3), where the C—H bonds are of low acidity. More significantly, methyl groups are, in general, likely to be undergoing very fast rotation about the adjacent C—C bond in the solid state (Riddell & Rogerson, 1996 , 1997 ). For methyl groups bonded to planar fragments such as aryl rings, the sixfold barrier to rotation is usually very small, only a few J mol⁻¹ rather than the typical order of magnitude in kJ mol⁻¹ (Naylor & Wilson, 1957 ; Tannenbaum et al., 1956 ). Hence, this contact cannot be regarded as structurally significant. There are π–π stacking interactions in each structure.

Table 3
Parameters (Å, °) for hydrogen bonds and short intermolecular contacts in compounds (I)–(III)

Cg1 represents the centroid of the N1/C2//C4/C4A/C8A ring.

	D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
(I)	C8—H8⋯N1ⁱ	0.95	2.62	3.561 (2)	170
(II)	C7—H7⋯N1ⁱⁱ	0.95	2.75	3.678 (3)	168
	C426—H426⋯Cg1ⁱⁱⁱ	0.95	2.86	3.3627 (17)	114
(III)	C21—H21A⋯N1^iv	0.98	2.63	3.594 (3)	170
Symmetry codes: (i) −x + 1, −y, −z + 1; (ii) −x + $[{1\over 2}]$ , y − $[{1\over 2}]$ , −z + $[{3\over 2}]$ ; (iii) −x + 1, −y + 1, −z + 1; (iv) −x + 1, −y + 2, −z + 1.

In the structure of (I), inversion-related pairs of molecules are linked by almost linear C—H⋯N hydrogen bonds (Table 3) to form centrosymmetric dimers characterized by an R₂²(8) motif (Etter, 1990 ; Etter et al., 1990 ; Bernstein et al., 1995 ) (Fig. 4). Dimers of this type are linked into sheets by π–π stacking interactions; the quinoline units of the molecule at (x, y, z), makes dihedral angles of 9.21 (7)° with the corresponding rings of the molecules at (x, −y + $[{1\over 2}]$ , z + $[{1\over 2}]$ ) and (x, −y + $[{1\over 2}]$ , z − $[{1\over 2}]$ ), with ring-centroid separations of 3.7682 (9) Å in each case, with the shortest distance between the centroid of one ring and the plane of the other of 3.5610 (6) Å. The combination of inversion and glide-plane operations leads to the formation of a sheet of π-stacked dimers lying parallel to (100) (Fig. 4).

Figure 4
Part of the crystal structure of compound (I)

, showing the formation of a π-stacked sheet of hydrogen-bonded dimers lying parallel to (100). Hydrogen bonds are drawn as dashed lines and, for the sake of clarity, H atoms not involved in the motif shown have been omitted.

In the structure of compound (II), inversion-related pairs of molecules are linked by a C—H⋯π(arene) hydrogen bond to form centrosymmetric dimers (Fig. 5), and these dimers are linked into chains by a single π–π stacking interaction; the heterocyclic rings in the molecules at (x, y, z) and (−x + 1, y, −z + $[{3\over 2}]$ ) are strictly parallel, with an interplanar spacing of 3.5058 (6) Å and a ring-centroid separation of 3.6845 (9) Å, corresponding to a ring-centroid offset of 1.1335 (12) Å. By this means, the hydrogen-bonded dimers are linked into a chain running parallel to [001] (Fig. 5).

Figure 5
Part of the crystal structure of compound (II)

, showing the formation of a π-stacked chain of hydrogen-bonded dimers running parallel to [001] Hydrogen bonds are drawn as dashed lines and, for the sake of clarity, H atoms not involved in the motif shown have been omitted.

Although there are no hydrogen bonds in the structure of compound (III), the molecules which are related by translation along the [010] direction are stacked precisely in register with a spacing equal to the unit-cell vector b = 3.8629 (2) Å (Fig. 6). Eight stacks of this kind pass through each unit cell (Fig. 7), but there are no direction-specific interactions between adjacent stacks.

Figure 6
Part of the crystal structure of compound (III)

, showing the formation of a π-stacked chain of hydrogen-bonded dimers running parallel to [010]. Hydrogen bonds are drawn as dashed lines and, for the sake of clarity, H atoms not involved in the motif shown have been omitted.

Figure 7
A projection along [010] of part of the crystal structure of compound (III)

, showing the arrangement of the molecular stacks within the unit cell. For the sake of clarity, all H atoms have been omitted.

We have previously reported (Rodríguez et al., 2020) the synthesis and structures of a number of 4-styrylquinoline derivatives carrying either acetyl or carboethoxy substituents at position C-3. Of these, three closely related acetyl derivatives were found to be isomorphous, with their molecules linked into simple C(6) chains by a single C—H⋯O hydrogen bond. By contrast, the matching set of carboethoxy derivatives all exhibited different crystallization characteristics and different modes of supramolecular assembly, with one forming C(13) chains and the other two forming cyclic centrosymmetric dimers involving C—H⋯O hydrogen bonds in one case and C—H⋯π hydrogen bonds in the other. In addition, two other examples carrying acyl substituents have been reported (Meléndez et al., 2020) on a proof-of-structure basis without detailed structure analysis or description, but subsequent re-examination (Rodríguez et al., 2020) found a complex sheet structure in one of them, but no significant intermolecular interactions in the other.

The structures of a number of other styrylquinolines are recorded in the Cambridge Structural Database (CSD; Groom et al., 2016 ), but it is striking that the majority of these structures are of 2-styrylquinoline derivatives, along with those of a small number of 8-styrylquinolines. This may reflect, at least in part, a lack of efficient, straightforward and versatile routes to other isomeric styrylquinolines. The structure of 2-styrylquinoline itself has been reported three times (Valle et al., 1986 ; Gulakova et al., 2011 ; Kuz'mina et al., 2011 ), as have those of 2-[2-(4-methylphenyl)vinyl]quinoline (Gulakova et al., 2011; Kuz'mina et al., 2011; Das et al., 2019 ) and 2-[2-(3,4-methoxyphenyl)vinyl]quinolone (Gulakova et al., 2011; Kuz'mina et al., 2011; Sharma et al., 2021 ). There are two reports on the structure of 2-[2-(3-nitrophenyl)vinyl]quinoline (Gulakova et al., 2011; Kuz'mina et al., 2011) and one on the structure of 4-phenyl-2-styrylquinoline (Makela et al., 2021 ). In all of these 2-styrylquinolines, the molecular skeleton is planar, in marked contrast to the nonplanar conformations of the 4-styrylquinoline derivatives (I)–(III) reported here, and of those reported previously (Rodríguez et al., 2020). In both 8-styrylquinoline and 8-[2-(biphenyl-4-yl)vinyl]-2-methylquinoline, the styrylquinoline fragment is planar (Sharma et al., 2015 ), as found in 2-styrylquinolines but again in marked contrast to 4-styrylquinolines. It is not easy to see why 4-styrylquinolines should adopt nonplanar conformations, while molecules of the 2-styryl and 8-styryl isomers appear consistently to adopt planar forms.

Supporting information

CCDC references: 2204061; 2204060; 2204059

Crystal structure: contains datablocks global, I, II, III. DOI: https://doi.org/10.1107/S2053229622008634/ky3221sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2053229622008634/ky3221Isup2.hkl

Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S2053229622008634/ky3221IIsup3.hkl

Structure factors: contains datablock III. DOI: https://doi.org/10.1107/S2053229622008634/ky3221IIIsup5.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2053229622008634/ky3221Isup5.cml

Supporting information file. DOI: https://doi.org/10.1107/S2053229622008634/ky3221IIsup6.cml

Supporting information file. DOI: https://doi.org/10.1107/S2053229622008634/ky3221IIIsup7.cml

Computing details top

For all structures, data collection: APEX3 (Bruker, 2018); cell refinement: SAINT (Bruker, 2017); data reduction: SAINT (Bruker, 2017); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2020); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b) and PLATON (Spek, 2020).

(E)-4-[2-(4-Fluorophenyl)ethenyl]-2-methylquinoline (I) top

Crystal data top

C₁₈H₁₄FN	F(000) = 552
M_r = 263.30	D_x = 1.364 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.5921 (7) Å	Cell parameters from 2950 reflections
b = 12.7103 (6) Å	θ = 2.2–27.5°
c = 7.6215 (3) Å	µ = 0.09 mm⁻¹
β = 103.133 (2)°	T = 100 K
V = 1282.25 (10) Å³	Needle, yellow
Z = 4	0.20 × 0.08 × 0.07 mm

Data collection top

Bruker D8 Venture diffractometer	2949 independent reflections
Radiation source: INCOATEC high brilliance microfocus sealed tube	2342 reflections with I > 2σ(I)
Multilayer mirror monochromator	R_int = 0.079
φ and ω scans	θ_max = 27.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2016)	h = −17→17
T_min = 0.934, T_max = 0.994	k = −16→16
38068 measured reflections	l = −9→9

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.042	H-atom parameters constrained
wR(F²) = 0.100	w = 1/[σ²(F_o²) + (0.0315P)² + 0.8512P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
2949 reflections	Δρ_max = 0.26 e Å⁻³
182 parameters	Δρ_min = −0.22 e Å⁻³
0 restraints

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
N1	0.38298 (9)	0.09596 (10)	0.33198 (16)	0.0184 (3)
C2	0.29100 (11)	0.11467 (12)	0.23444 (19)	0.0176 (3)
C3	0.25558 (11)	0.21776 (12)	0.18306 (19)	0.0176 (3)
H3	0.1892	0.2272	0.1115	0.021*
C4	0.31611 (11)	0.30404 (11)	0.23560 (19)	0.0167 (3)
C4A	0.41653 (10)	0.28596 (11)	0.33921 (19)	0.0163 (3)
C5	0.48647 (11)	0.36772 (12)	0.4033 (2)	0.0191 (3)
H5	0.4685	0.4386	0.3719	0.023*
C6	0.57984 (11)	0.34538 (12)	0.5101 (2)	0.0204 (3)
H6	0.6260	0.4008	0.5523	0.024*
C7	0.60735 (11)	0.24060 (12)	0.5574 (2)	0.0204 (3)
H7	0.6716	0.2261	0.6336	0.024*
C8	0.54267 (11)	0.15932 (12)	0.4950 (2)	0.0196 (3)
H8	0.5628	0.0889	0.5257	0.024*
C8A	0.44577 (11)	0.18016 (11)	0.38490 (19)	0.0170 (3)
C21	0.22304 (12)	0.02127 (12)	0.1834 (2)	0.0225 (3)
H21A	0.1914	0.0036	0.2830	0.034*
H21B	0.2628	−0.0388	0.1578	0.034*
H21C	0.1705	0.0381	0.0759	0.034*
C41	0.27793 (11)	0.41183 (11)	0.19305 (19)	0.0174 (3)
H41	0.3216	0.4626	0.1597	0.021*
C42	0.18432 (11)	0.44098 (11)	0.19947 (19)	0.0173 (3)
H42	0.1420	0.3877	0.2295	0.021*
C421	0.13959 (10)	0.54644 (11)	0.16520 (18)	0.0163 (3)
C422	0.04269 (11)	0.56378 (12)	0.1940 (2)	0.0191 (3)
H422	0.0077	0.5074	0.2345	0.023*
C423	−0.00317 (11)	0.66179 (12)	0.1644 (2)	0.0199 (3)
H423	−0.0691	0.6729	0.1835	0.024*
C424	0.04914 (11)	0.74221 (11)	0.10693 (19)	0.0187 (3)
F424	0.00528 (7)	0.83934 (7)	0.08198 (12)	0.0255 (2)
C425	0.14458 (11)	0.72940 (12)	0.0748 (2)	0.0192 (3)
H425	0.1785	0.7863	0.0333	0.023*
C426	0.18939 (11)	0.63090 (12)	0.10502 (19)	0.0181 (3)
H426	0.2551	0.6206	0.0845	0.022*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0183 (6)	0.0176 (6)	0.0200 (6)	0.0012 (5)	0.0059 (5)	0.0007 (5)
C2	0.0186 (7)	0.0177 (7)	0.0181 (7)	−0.0004 (6)	0.0075 (6)	−0.0006 (5)
C3	0.0159 (7)	0.0197 (7)	0.0177 (7)	0.0016 (6)	0.0050 (5)	0.0006 (5)
C4	0.0171 (7)	0.0175 (7)	0.0167 (7)	0.0023 (6)	0.0066 (5)	0.0014 (5)
C4A	0.0164 (7)	0.0177 (7)	0.0157 (7)	0.0010 (5)	0.0058 (5)	−0.0003 (5)
C5	0.0200 (7)	0.0164 (7)	0.0215 (7)	0.0020 (6)	0.0058 (6)	−0.0019 (6)
C6	0.0171 (7)	0.0220 (8)	0.0221 (7)	−0.0019 (6)	0.0046 (6)	−0.0052 (6)
C7	0.0158 (7)	0.0255 (8)	0.0198 (7)	0.0038 (6)	0.0038 (6)	−0.0014 (6)
C8	0.0184 (7)	0.0207 (8)	0.0205 (7)	0.0047 (6)	0.0057 (6)	0.0015 (6)
C8A	0.0180 (7)	0.0172 (7)	0.0172 (7)	0.0014 (5)	0.0071 (5)	−0.0002 (5)
C21	0.0231 (8)	0.0182 (8)	0.0259 (8)	−0.0017 (6)	0.0048 (6)	−0.0010 (6)
C41	0.0179 (7)	0.0164 (7)	0.0175 (7)	−0.0003 (6)	0.0035 (5)	0.0007 (5)
C42	0.0178 (7)	0.0161 (7)	0.0179 (7)	−0.0013 (5)	0.0041 (5)	0.0008 (5)
C421	0.0152 (7)	0.0169 (7)	0.0159 (7)	0.0003 (5)	0.0016 (5)	−0.0012 (5)
C422	0.0178 (7)	0.0195 (8)	0.0204 (7)	−0.0013 (6)	0.0051 (6)	0.0011 (5)
C423	0.0168 (7)	0.0239 (8)	0.0192 (7)	0.0040 (6)	0.0049 (6)	−0.0008 (6)
C424	0.0221 (8)	0.0153 (7)	0.0173 (7)	0.0060 (6)	0.0016 (6)	−0.0006 (5)
F424	0.0298 (5)	0.0174 (5)	0.0296 (5)	0.0095 (4)	0.0076 (4)	0.0024 (4)
C425	0.0201 (7)	0.0162 (7)	0.0207 (7)	−0.0014 (6)	0.0030 (6)	0.0002 (5)
C426	0.0152 (7)	0.0195 (7)	0.0193 (7)	0.0002 (5)	0.0030 (5)	−0.0001 (6)

Geometric parameters (Å, º) top

N1—C2	1.3227 (19)	C21—H21A	0.9800
N1—C8A	1.3712 (19)	C21—H21B	0.9800
C2—C3	1.420 (2)	C21—H21C	0.9800
C2—C21	1.500 (2)	C41—C42	1.337 (2)
C3—C4	1.375 (2)	C41—H41	0.9500
C3—H3	0.9500	C42—C421	1.471 (2)
C4—C4A	1.432 (2)	C42—H42	0.9500
C4—C41	1.475 (2)	C421—C426	1.401 (2)
C4A—C5	1.418 (2)	C421—C422	1.401 (2)
C4A—C8A	1.423 (2)	C422—C423	1.388 (2)
C5—C6	1.373 (2)	C422—H422	0.9500
C5—H5	0.9500	C423—C424	1.373 (2)
C6—C7	1.408 (2)	C423—H423	0.9500
C6—H6	0.9500	C424—F424	1.3653 (16)
C7—C8	1.370 (2)	C424—C425	1.383 (2)
C7—H7	0.9500	C425—C426	1.388 (2)
C8—C8A	1.417 (2)	C425—H425	0.9500
C8—H8	0.9500	C426—H426	0.9500

C2—N1—C8A	118.08 (13)	C2—C21—H21B	109.5
N1—C2—C3	122.60 (13)	H21A—C21—H21B	109.5
N1—C2—C21	116.82 (13)	C2—C21—H21C	109.5
C3—C2—C21	120.56 (13)	H21A—C21—H21C	109.5
C4—C3—C2	120.85 (13)	H21B—C21—H21C	109.5
C4—C3—H3	119.6	C42—C41—C4	122.66 (14)
C2—C3—H3	119.6	C42—C41—H41	118.7
C3—C4—C4A	117.71 (13)	C4—C41—H41	118.7
C3—C4—C41	121.31 (13)	C41—C42—C421	127.21 (14)
C4A—C4—C41	120.94 (13)	C41—C42—H42	116.4
C5—C4A—C8A	118.70 (13)	C421—C42—H42	116.4
C5—C4A—C4	123.56 (13)	C426—C421—C422	118.18 (13)
C8A—C4A—C4	117.71 (13)	C426—C421—C42	123.07 (13)
C6—C5—C4A	120.64 (14)	C422—C421—C42	118.76 (13)
C6—C5—H5	119.7	C423—C422—C421	121.28 (14)
C4A—C5—H5	119.7	C423—C422—H422	119.4
C5—C6—C7	120.23 (14)	C421—C422—H422	119.4
C5—C6—H6	119.9	C424—C423—C422	118.29 (13)
C7—C6—H6	119.9	C424—C423—H423	120.9
C8—C7—C6	120.82 (14)	C422—C423—H423	120.9
C8—C7—H7	119.6	F424—C424—C423	118.45 (13)
C6—C7—H7	119.6	F424—C424—C425	118.63 (13)
C7—C8—C8A	120.11 (14)	C423—C424—C425	122.92 (14)
C7—C8—H8	119.9	C424—C425—C426	118.07 (14)
C8A—C8—H8	119.9	C424—C425—H425	121.0
N1—C8A—C8	117.46 (13)	C426—C425—H425	121.0
N1—C8A—C4A	123.03 (13)	C425—C426—C421	121.26 (13)
C8—C8A—C4A	119.48 (13)	C425—C426—H426	119.4
C2—C21—H21A	109.5	C421—C426—H426	119.4

C8A—N1—C2—C3	0.1 (2)	C5—C4A—C8A—N1	178.89 (13)
C8A—N1—C2—C21	−178.20 (13)	C4—C4A—C8A—N1	1.0 (2)
N1—C2—C3—C4	−0.9 (2)	C5—C4A—C8A—C8	1.1 (2)
C21—C2—C3—C4	177.35 (13)	C4—C4A—C8A—C8	−176.78 (13)
C2—C3—C4—C4A	1.7 (2)	C3—C4—C41—C42	38.8 (2)
C2—C3—C4—C41	−175.99 (13)	C4A—C4—C41—C42	−138.76 (15)
C3—C4—C4A—C5	−179.48 (13)	C4—C41—C42—C421	178.04 (14)
C41—C4—C4A—C5	−1.8 (2)	C41—C42—C421—C426	5.5 (2)
C3—C4—C4A—C8A	−1.72 (19)	C41—C42—C421—C422	−174.47 (15)
C41—C4—C4A—C8A	175.96 (13)	C426—C421—C422—C423	−0.2 (2)
C8A—C4A—C5—C6	−1.2 (2)	C42—C421—C422—C423	179.79 (14)
C4—C4A—C5—C6	176.49 (14)	C421—C422—C423—C424	−0.4 (2)
C4A—C5—C6—C7	0.0 (2)	C422—C423—C424—F424	−178.42 (13)
C5—C6—C7—C8	1.4 (2)	C422—C423—C424—C425	1.0 (2)
C6—C7—C8—C8A	−1.5 (2)	F424—C424—C425—C426	178.42 (13)
C2—N1—C8A—C8	177.65 (13)	C423—C424—C425—C426	−1.0 (2)
C2—N1—C8A—C4A	−0.2 (2)	C424—C425—C426—C421	0.4 (2)
C7—C8—C8A—N1	−177.65 (13)	C422—C421—C426—C425	0.2 (2)
C7—C8—C8A—C4A	0.3 (2)	C42—C421—C426—C425	−179.79 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···N1ⁱ	0.95	2.62	3.561 (2)	170

Symmetry code: (i) −x+1, −y, −z+1.

(E)-2-Methyl-4-{2-[4-(trifluoromethyl)phenyl]ethenyl}quinoline (II) top

Crystal data top

C₁₉H₁₄F₃N	F(000) = 1296
M_r = 313.31	D_x = 1.381 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 17.2696 (10) Å	Cell parameters from 3752 reflections
b = 10.8096 (7) Å	θ = 2.2–28.3°
c = 16.1495 (8) Å	µ = 0.11 mm⁻¹
β = 91.440 (2)°	T = 100 K
V = 3013.8 (3) Å³	Block, colourless
Z = 8	0.16 × 0.14 × 0.12 mm

Data collection top

Bruker D8 Venture diffractometer	3750 independent reflections
Radiation source: INCOATEC high brilliance microfocus sealed tube	2921 reflections with I > 2σ(I)
Multilayer mirror monochromator	R_int = 0.085
φ and ω scans	θ_max = 28.3°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2016)	h = −22→22
T_min = 0.888, T_max = 0.987	k = −14→14
46287 measured reflections	l = −21→20

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.047	H-atom parameters constrained
wR(F²) = 0.121	w = 1/[σ²(F_o²) + (0.0491P)² + 3.926P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
3750 reflections	Δρ_max = 0.33 e Å⁻³
209 parameters	Δρ_min = −0.29 e Å⁻³
0 restraints

Special details top

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

	x	y	z	U_iso*/U_eq
N1	0.35530 (8)	0.65666 (13)	0.70993 (8)	0.0214 (3)
C2	0.40811 (9)	0.73252 (15)	0.68089 (10)	0.0220 (3)
C3	0.47497 (9)	0.69044 (15)	0.64043 (10)	0.0208 (3)
H3	0.5106	0.7490	0.6197	0.025*
C4	0.48905 (9)	0.56618 (15)	0.63077 (9)	0.0184 (3)
C4A	0.43320 (9)	0.48166 (15)	0.66242 (9)	0.0176 (3)
C5	0.44046 (9)	0.35106 (15)	0.65886 (10)	0.0216 (3)
H5	0.4847	0.3153	0.6345	0.026*
C6	0.38443 (10)	0.27589 (16)	0.69007 (10)	0.0242 (3)
H6	0.3905	0.1886	0.6874	0.029*
C7	0.31786 (10)	0.32625 (16)	0.72612 (10)	0.0245 (4)
H7	0.2789	0.2732	0.7465	0.029*
C8	0.30976 (9)	0.45181 (16)	0.73152 (10)	0.0221 (3)
H8	0.2651	0.4855	0.7562	0.026*
C8A	0.36711 (9)	0.53235 (15)	0.70072 (9)	0.0187 (3)
C21	0.39360 (11)	0.86894 (16)	0.69174 (13)	0.0324 (4)
H21A	0.3714	0.8837	0.7461	0.049*
H21B	0.3574	0.8978	0.6482	0.049*
H21C	0.4426	0.9141	0.6879	0.049*
C41	0.55777 (9)	0.52090 (15)	0.58805 (9)	0.0189 (3)
H41	0.5541	0.4430	0.5610	0.023*
C42	0.62479 (9)	0.58178 (15)	0.58464 (10)	0.0205 (3)
H42	0.6276	0.6595	0.6120	0.025*
C421	0.69464 (9)	0.54044 (15)	0.54269 (9)	0.0181 (3)
C422	0.76181 (9)	0.61241 (16)	0.55017 (10)	0.0224 (3)
H422	0.7611	0.6860	0.5824	0.027*
C423	0.82949 (9)	0.57845 (15)	0.51149 (10)	0.0229 (3)
H423	0.8747	0.6282	0.5172	0.027*
C424	0.83043 (9)	0.47101 (15)	0.46437 (9)	0.0188 (3)
C425	0.76429 (9)	0.39804 (15)	0.45619 (9)	0.0196 (3)
H425	0.7652	0.3246	0.4239	0.024*
C426	0.69721 (9)	0.43241 (15)	0.49513 (10)	0.0198 (3)
H426	0.6523	0.3820	0.4895	0.024*
C427	0.90242 (9)	0.43013 (16)	0.42322 (10)	0.0232 (3)
F471	0.93775 (6)	0.33641 (11)	0.46404 (8)	0.0390 (3)
F472	0.88912 (7)	0.38927 (13)	0.34613 (7)	0.0460 (3)
F473	0.95562 (6)	0.51919 (11)	0.41781 (8)	0.0390 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0182 (7)	0.0233 (7)	0.0229 (7)	0.0019 (5)	0.0041 (5)	−0.0005 (5)
C2	0.0196 (8)	0.0223 (8)	0.0245 (8)	0.0015 (6)	0.0053 (6)	0.0003 (6)
C3	0.0168 (7)	0.0223 (8)	0.0236 (8)	−0.0009 (6)	0.0048 (6)	0.0016 (6)
C4	0.0154 (7)	0.0235 (8)	0.0162 (7)	0.0020 (6)	0.0002 (5)	−0.0001 (6)
C4A	0.0160 (7)	0.0218 (8)	0.0150 (7)	0.0001 (6)	−0.0010 (5)	0.0004 (6)
C5	0.0208 (8)	0.0224 (8)	0.0216 (7)	0.0016 (6)	0.0010 (6)	−0.0013 (6)
C6	0.0270 (9)	0.0213 (8)	0.0241 (8)	−0.0028 (7)	−0.0003 (6)	0.0003 (6)
C7	0.0226 (8)	0.0278 (9)	0.0233 (8)	−0.0066 (7)	0.0022 (6)	0.0012 (6)
C8	0.0174 (7)	0.0280 (9)	0.0210 (7)	−0.0021 (6)	0.0033 (6)	−0.0005 (6)
C8A	0.0171 (7)	0.0228 (8)	0.0163 (7)	0.0005 (6)	0.0004 (6)	0.0004 (6)
C21	0.0306 (10)	0.0227 (9)	0.0448 (11)	0.0030 (7)	0.0160 (8)	−0.0003 (8)
C41	0.0173 (7)	0.0210 (7)	0.0186 (7)	0.0030 (6)	0.0013 (6)	0.0000 (6)
C42	0.0187 (7)	0.0225 (8)	0.0205 (7)	0.0012 (6)	0.0015 (6)	−0.0019 (6)
C421	0.0159 (7)	0.0217 (8)	0.0169 (7)	0.0007 (6)	0.0013 (5)	0.0011 (6)
C422	0.0196 (8)	0.0223 (8)	0.0254 (8)	−0.0014 (6)	0.0020 (6)	−0.0057 (6)
C423	0.0175 (8)	0.0236 (8)	0.0277 (8)	−0.0042 (6)	0.0021 (6)	−0.0033 (6)
C424	0.0160 (7)	0.0217 (8)	0.0189 (7)	0.0014 (6)	0.0013 (6)	0.0017 (6)
C425	0.0193 (7)	0.0199 (7)	0.0197 (7)	−0.0003 (6)	0.0018 (6)	−0.0021 (6)
C426	0.0158 (7)	0.0218 (8)	0.0220 (7)	−0.0025 (6)	0.0010 (6)	−0.0010 (6)
C427	0.0201 (8)	0.0248 (8)	0.0251 (8)	−0.0019 (6)	0.0041 (6)	−0.0024 (6)
F471	0.0287 (6)	0.0367 (6)	0.0522 (7)	0.0131 (5)	0.0118 (5)	0.0077 (5)
F472	0.0307 (6)	0.0758 (9)	0.0318 (6)	−0.0015 (6)	0.0096 (5)	−0.0237 (6)
F473	0.0274 (6)	0.0328 (6)	0.0578 (7)	−0.0076 (5)	0.0212 (5)	−0.0055 (5)

Geometric parameters (Å, º) top

N1—C2	1.321 (2)	C21—H21C	0.9800
N1—C8A	1.368 (2)	C41—C42	1.334 (2)
C2—C3	1.416 (2)	C41—H41	0.9500
C2—C21	1.507 (2)	C42—C421	1.468 (2)
C3—C4	1.375 (2)	C42—H42	0.9500
C3—H3	0.9500	C421—C426	1.399 (2)
C4—C4A	1.432 (2)	C421—C422	1.400 (2)
C4—C41	1.471 (2)	C422—C423	1.388 (2)
C4A—C5	1.419 (2)	C422—H422	0.9500
C4A—C8A	1.422 (2)	C423—C424	1.389 (2)
C5—C6	1.369 (2)	C423—H423	0.9500
C5—H5	0.9500	C424—C425	1.392 (2)
C6—C7	1.411 (2)	C424—C427	1.491 (2)
C6—H6	0.9500	C425—C426	1.383 (2)
C7—C8	1.368 (2)	C425—H425	0.9500
C7—H7	0.9500	C426—H426	0.9500
C8—C8A	1.418 (2)	C427—F473	1.3350 (19)
C8—H8	0.9500	C427—F472	1.335 (2)
C21—H21A	0.9800	C427—F471	1.347 (2)
C21—H21B	0.9800

C2—N1—C8A	117.72 (14)	H21A—C21—H21C	109.5
N1—C2—C3	122.85 (15)	H21B—C21—H21C	109.5
N1—C2—C21	116.62 (14)	C42—C41—C4	124.49 (15)
C3—C2—C21	120.53 (15)	C42—C41—H41	117.8
C4—C3—C2	120.99 (15)	C4—C41—H41	117.8
C4—C3—H3	119.5	C41—C42—C421	126.36 (15)
C2—C3—H3	119.5	C41—C42—H42	116.8
C3—C4—C4A	117.40 (14)	C421—C42—H42	116.8
C3—C4—C41	121.69 (14)	C426—C421—C422	118.27 (14)
C4A—C4—C41	120.90 (14)	C426—C421—C42	123.05 (14)
C5—C4A—C8A	118.29 (14)	C422—C421—C42	118.68 (14)
C5—C4A—C4	124.02 (14)	C423—C422—C421	121.30 (15)
C8A—C4A—C4	117.69 (14)	C423—C422—H422	119.4
C6—C5—C4A	120.77 (15)	C421—C422—H422	119.4
C6—C5—H5	119.6	C422—C423—C424	119.29 (15)
C4A—C5—H5	119.6	C422—C423—H423	120.4
C5—C6—C7	120.90 (16)	C424—C423—H423	120.4
C5—C6—H6	119.5	C423—C424—C425	120.34 (14)
C7—C6—H6	119.5	C423—C424—C427	120.88 (14)
C8—C7—C6	119.67 (15)	C425—C424—C427	118.77 (14)
C8—C7—H7	120.2	C426—C425—C424	119.97 (15)
C6—C7—H7	120.2	C426—C425—H425	120.0
C7—C8—C8A	120.89 (15)	C424—C425—H425	120.0
C7—C8—H8	119.6	C425—C426—C421	120.83 (14)
C8A—C8—H8	119.6	C425—C426—H426	119.6
N1—C8A—C8	117.23 (14)	C421—C426—H426	119.6
N1—C8A—C4A	123.33 (14)	F473—C427—F472	106.26 (14)
C8—C8A—C4A	119.44 (15)	F473—C427—F471	105.69 (14)
C2—C21—H21A	109.5	F472—C427—F471	105.82 (14)
C2—C21—H21B	109.5	F473—C427—C424	113.47 (14)
H21A—C21—H21B	109.5	F472—C427—C424	112.81 (14)
C2—C21—H21C	109.5	F471—C427—C424	112.17 (13)

C8A—N1—C2—C3	0.7 (2)	C4—C4A—C8A—C8	178.87 (14)
C8A—N1—C2—C21	179.91 (15)	C3—C4—C41—C42	28.1 (2)
N1—C2—C3—C4	−1.3 (3)	C4A—C4—C41—C42	−153.27 (16)
C21—C2—C3—C4	179.50 (16)	C4—C41—C42—C421	−179.85 (15)
C2—C3—C4—C4A	0.6 (2)	C41—C42—C421—C426	4.6 (3)
C2—C3—C4—C41	179.28 (15)	C41—C42—C421—C422	−175.68 (16)
C3—C4—C4A—C5	−178.50 (15)	C426—C421—C422—C423	0.2 (2)
C41—C4—C4A—C5	2.8 (2)	C42—C421—C422—C423	−179.59 (15)
C3—C4—C4A—C8A	0.6 (2)	C421—C422—C423—C424	0.1 (3)
C41—C4—C4A—C8A	−178.12 (13)	C422—C423—C424—C425	−0.2 (2)
C8A—C4A—C5—C6	1.3 (2)	C422—C423—C424—C427	−178.80 (15)
C4—C4A—C5—C6	−179.65 (15)	C423—C424—C425—C426	0.0 (2)
C4A—C5—C6—C7	0.4 (2)	C427—C424—C425—C426	178.65 (15)
C5—C6—C7—C8	−1.3 (3)	C424—C425—C426—C421	0.3 (2)
C6—C7—C8—C8A	0.5 (2)	C422—C421—C426—C425	−0.3 (2)
C2—N1—C8A—C8	−179.51 (14)	C42—C421—C426—C425	179.40 (15)
C2—N1—C8A—C4A	0.6 (2)	C423—C424—C427—F473	−16.7 (2)
C7—C8—C8A—N1	−178.81 (15)	C425—C424—C427—F473	164.64 (15)
C7—C8—C8A—C4A	1.1 (2)	C423—C424—C427—F472	−137.61 (16)
C5—C4A—C8A—N1	177.91 (14)	C425—C424—C427—F472	43.7 (2)
C4—C4A—C8A—N1	−1.2 (2)	C423—C424—C427—F471	102.99 (18)
C5—C4A—C8A—C8	−2.0 (2)	C425—C424—C427—F471	−75.67 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C426—H426···Cg1ⁱ	0.95	2.86	3.3627 (17)	114

Symmetry code: (i) −x+1, −y+1, −z+1.

(E)-4-[2-(2,6-dichlorophenyl)ethenyl]-2-methylquinoline (III) top

Crystal data top

C₁₈H₁₃Cl₂N	F(000) = 1296
M_r = 314.19	D_x = 1.478 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 30.5651 (15) Å	Cell parameters from 3210 reflections
b = 3.8629 (2) Å	θ = 2.6–27.5°
c = 25.5357 (13) Å	µ = 0.45 mm⁻¹
β = 110.497 (2)°	T = 100 K
V = 2824.1 (2) Å³	Needle, yellow
Z = 8	0.20 × 0.10 × 0.06 mm

Data collection top

Bruker D8 Venture diffractometer	3208 independent reflections
Radiation source: INCOATEC high brilliance microfocus sealed tube	2930 reflections with I > 2σ(I)
Multilayer mirror monochromator	R_int = 0.042
φ and ω scans	θ_max = 27.5°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2016)	h = −38→38
T_min = 0.897, T_max = 0.973	k = −5→4
28110 measured reflections	l = −33→33

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.031	H-atom parameters constrained
wR(F²) = 0.079	w = 1/[σ²(F_o²) + (0.0342P)² + 4.0386P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
3208 reflections	Δρ_max = 0.33 e Å⁻³
191 parameters	Δρ_min = −0.26 e Å⁻³
0 restraints

Special details top

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

	x	y	z	U_iso*/U_eq
N1	0.56531 (4)	0.8852 (3)	0.48948 (5)	0.0130 (2)
C2	0.54198 (5)	0.7306 (3)	0.44182 (6)	0.0128 (3)
C3	0.56318 (5)	0.6274 (4)	0.40297 (6)	0.0137 (3)
H3	0.5448	0.5189	0.3690	0.016*
C4	0.60991 (5)	0.6819 (4)	0.41372 (5)	0.0125 (3)
C4A	0.63640 (5)	0.8465 (4)	0.46545 (5)	0.0119 (3)
C5	0.68484 (5)	0.9218 (4)	0.48195 (6)	0.0138 (3)
H5	0.7014	0.8612	0.4580	0.017*
C6	0.70793 (5)	1.0802 (4)	0.53186 (6)	0.0150 (3)
H6	0.7405	1.1247	0.5426	0.018*
C7	0.68373 (5)	1.1781 (4)	0.56761 (6)	0.0151 (3)
H7	0.7000	1.2881	0.6023	0.018*
C8	0.63677 (5)	1.1148 (4)	0.55238 (6)	0.0136 (3)
H8	0.6206	1.1858	0.5763	0.016*
C8A	0.61204 (5)	0.9449 (3)	0.50145 (5)	0.0118 (3)
C21	0.49105 (5)	0.6559 (4)	0.42929 (6)	0.0161 (3)
H21A	0.4794	0.8008	0.4530	0.024*
H21B	0.4871	0.4113	0.4368	0.024*
H21C	0.4735	0.7070	0.3899	0.024*
C41	0.63227 (5)	0.5763 (4)	0.37352 (6)	0.0137 (3)
H41	0.6627	0.4787	0.3873	0.016*
C42	0.61108 (5)	0.6134 (4)	0.31843 (6)	0.0135 (3)
H42	0.5808	0.7145	0.3062	0.016*
C421	0.62973 (5)	0.5137 (4)	0.27438 (5)	0.0123 (3)
C422	0.59998 (5)	0.3598 (4)	0.22471 (6)	0.0135 (3)
Cl42	0.54280 (2)	0.25868 (9)	0.21885 (2)	0.01765 (10)
C423	0.61385 (5)	0.2738 (4)	0.18021 (6)	0.0154 (3)
H423	0.5925	0.1695	0.1475	0.018*
C424	0.65948 (5)	0.3429 (4)	0.18423 (6)	0.0163 (3)
H424	0.6696	0.2848	0.1542	0.020*
C425	0.69023 (5)	0.4961 (4)	0.23194 (6)	0.0148 (3)
H425	0.7214	0.5450	0.2346	0.018*
C426	0.67535 (5)	0.5782 (4)	0.27589 (6)	0.0130 (3)
Cl46	0.71648 (2)	0.77500 (9)	0.33402 (2)	0.01667 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0133 (5)	0.0127 (6)	0.0132 (5)	0.0006 (4)	0.0048 (4)	0.0009 (4)
C2	0.0125 (6)	0.0112 (6)	0.0143 (6)	0.0010 (5)	0.0043 (5)	0.0018 (5)
C3	0.0145 (6)	0.0146 (7)	0.0108 (6)	0.0001 (5)	0.0028 (5)	−0.0003 (5)
C4	0.0152 (6)	0.0113 (6)	0.0107 (6)	0.0022 (5)	0.0043 (5)	0.0022 (5)
C4A	0.0126 (6)	0.0113 (6)	0.0113 (6)	0.0009 (5)	0.0035 (5)	0.0026 (5)
C5	0.0138 (6)	0.0144 (7)	0.0140 (6)	0.0016 (5)	0.0059 (5)	0.0027 (5)
C6	0.0116 (6)	0.0146 (7)	0.0176 (7)	−0.0002 (5)	0.0034 (5)	0.0033 (5)
C7	0.0169 (7)	0.0138 (7)	0.0120 (6)	−0.0008 (5)	0.0021 (5)	−0.0001 (5)
C8	0.0174 (7)	0.0128 (6)	0.0116 (6)	0.0011 (5)	0.0063 (5)	0.0007 (5)
C8A	0.0133 (6)	0.0101 (6)	0.0119 (6)	0.0010 (5)	0.0044 (5)	0.0025 (5)
C21	0.0135 (7)	0.0175 (7)	0.0178 (7)	−0.0010 (5)	0.0062 (5)	−0.0023 (6)
C41	0.0145 (6)	0.0132 (7)	0.0138 (6)	0.0018 (5)	0.0054 (5)	0.0006 (5)
C42	0.0120 (6)	0.0151 (7)	0.0140 (6)	0.0011 (5)	0.0055 (5)	−0.0006 (5)
C421	0.0140 (6)	0.0128 (6)	0.0095 (6)	0.0017 (5)	0.0035 (5)	0.0021 (5)
C422	0.0111 (6)	0.0150 (7)	0.0137 (6)	0.0013 (5)	0.0035 (5)	0.0021 (5)
Cl42	0.01233 (16)	0.0229 (2)	0.01625 (17)	−0.00152 (13)	0.00313 (13)	0.00075 (13)
C423	0.0188 (7)	0.0138 (7)	0.0125 (6)	0.0007 (5)	0.0041 (5)	−0.0011 (5)
C424	0.0209 (7)	0.0160 (7)	0.0142 (6)	0.0019 (6)	0.0089 (5)	0.0000 (5)
C425	0.0140 (6)	0.0151 (7)	0.0162 (6)	0.0012 (5)	0.0065 (5)	0.0013 (5)
C426	0.0135 (6)	0.0122 (6)	0.0116 (6)	0.0008 (5)	0.0022 (5)	0.0016 (5)
Cl46	0.01376 (17)	0.02144 (19)	0.01317 (16)	−0.00336 (13)	0.00267 (12)	−0.00164 (13)

Geometric parameters (Å, º) top

N1—C2	1.3186 (18)	C21—H21A	0.9800
N1—C8A	1.3713 (17)	C21—H21B	0.9800
C2—C3	1.4188 (19)	C21—H21C	0.9800
C2—C21	1.5034 (18)	C41—C42	1.3345 (19)
C3—C4	1.3730 (19)	C41—H41	0.9500
C3—H3	0.9500	C42—C421	1.4791 (18)
C4—C4A	1.4336 (19)	C42—H42	0.9500
C4—C41	1.4762 (18)	C421—C426	1.4035 (18)
C4A—C5	1.4203 (18)	C421—C422	1.4075 (18)
C4A—C8A	1.4227 (18)	C422—C423	1.3850 (19)
C5—C6	1.366 (2)	C422—Cl42	1.7454 (14)
C5—H5	0.9500	C423—C424	1.388 (2)
C6—C7	1.4130 (19)	C423—H423	0.9500
C6—H6	0.9500	C424—C425	1.384 (2)
C7—C8	1.3711 (19)	C424—H424	0.9500
C7—H7	0.9500	C425—C426	1.3874 (19)
C8—C8A	1.4159 (19)	C425—H425	0.9500
C8—H8	0.9500	C426—Cl46	1.7479 (14)

C2—N1—C8A	117.80 (12)	C2—C21—H21B	109.5
N1—C2—C3	122.74 (13)	H21A—C21—H21B	109.5
N1—C2—C21	117.92 (12)	C2—C21—H21C	109.5
C3—C2—C21	119.32 (12)	H21A—C21—H21C	109.5
C4—C3—C2	120.99 (13)	H21B—C21—H21C	109.5
C4—C3—H3	119.5	C42—C41—C4	122.10 (13)
C2—C3—H3	119.5	C42—C41—H41	119.0
C3—C4—C4A	117.69 (12)	C4—C41—H41	119.0
C3—C4—C41	121.40 (13)	C41—C42—C421	126.85 (13)
C4A—C4—C41	120.91 (12)	C41—C42—H42	116.6
C5—C4A—C8A	118.73 (12)	C421—C42—H42	116.6
C5—C4A—C4	123.91 (12)	C426—C421—C422	114.95 (12)
C8A—C4A—C4	117.34 (12)	C426—C421—C42	125.20 (12)
C6—C5—C4A	120.84 (13)	C422—C421—C42	119.73 (12)
C6—C5—H5	119.6	C423—C422—C421	123.63 (13)
C4A—C5—H5	119.6	C423—C422—Cl42	117.44 (11)
C5—C6—C7	120.43 (13)	C421—C422—Cl42	118.90 (10)
C5—C6—H6	119.8	C422—C423—C424	118.79 (13)
C7—C6—H6	119.8	C422—C423—H423	120.6
C8—C7—C6	120.11 (13)	C424—C423—H423	120.6
C8—C7—H7	119.9	C425—C424—C423	120.14 (13)
C6—C7—H7	119.9	C425—C424—H424	119.9
C7—C8—C8A	120.84 (13)	C423—C424—H424	119.9
C7—C8—H8	119.6	C424—C425—C426	119.72 (13)
C8A—C8—H8	119.6	C424—C425—H425	120.1
N1—C8A—C8	117.54 (12)	C426—C425—H425	120.1
N1—C8A—C4A	123.43 (12)	C425—C426—C421	122.76 (13)
C8—C8A—C4A	119.04 (12)	C425—C426—Cl46	116.38 (10)
C2—C21—H21A	109.5	C421—C426—Cl46	120.85 (10)

C8A—N1—C2—C3	−0.4 (2)	C5—C4A—C8A—C8	0.12 (19)
C8A—N1—C2—C21	178.35 (12)	C4—C4A—C8A—C8	−178.67 (12)
N1—C2—C3—C4	0.6 (2)	C3—C4—C41—C42	39.5 (2)
C21—C2—C3—C4	−178.06 (13)	C4A—C4—C41—C42	−140.35 (15)
C2—C3—C4—C4A	0.0 (2)	C4—C41—C42—C421	−179.23 (13)
C2—C3—C4—C41	−179.85 (13)	C41—C42—C421—C426	−44.5 (2)
C3—C4—C4A—C5	−179.50 (13)	C41—C42—C421—C422	139.58 (15)
C41—C4—C4A—C5	0.3 (2)	C426—C421—C422—C423	0.4 (2)
C3—C4—C4A—C8A	−0.78 (19)	C42—C421—C422—C423	176.74 (13)
C41—C4—C4A—C8A	179.06 (12)	C426—C421—C422—Cl42	178.52 (10)
C8A—C4A—C5—C6	1.1 (2)	C42—C421—C422—Cl42	−5.14 (18)
C4—C4A—C5—C6	179.83 (13)	C421—C422—C423—C424	−0.2 (2)
C4A—C5—C6—C7	−1.2 (2)	Cl42—C422—C423—C424	−178.36 (11)
C5—C6—C7—C8	0.0 (2)	C422—C423—C424—C425	−0.2 (2)
C6—C7—C8—C8A	1.3 (2)	C423—C424—C425—C426	0.5 (2)
C2—N1—C8A—C8	179.24 (12)	C424—C425—C426—C421	−0.3 (2)
C2—N1—C8A—C4A	−0.5 (2)	C424—C425—C426—Cl46	−179.35 (11)
C7—C8—C8A—N1	178.89 (13)	C422—C421—C426—C425	−0.2 (2)
C7—C8—C8A—C4A	−1.3 (2)	C42—C421—C426—C425	−176.27 (13)
C5—C4A—C8A—N1	179.88 (12)	C422—C421—C426—Cl46	178.89 (10)
C4—C4A—C8A—N1	1.1 (2)	C42—C421—C426—Cl46	2.8 (2)

Selected torsional angles (°) for compounds (I)–(III). top

Parameter	(I)	(II)	(III)
C3—C4—C41—C42	38.8 (2)	28.1 (2)	39.5 (2)
C41—C42—C421—C422	-174.47 (15)	-175.59 (15)	139.58 (15)

Parameters (Å, °) for hydrogen bonds and short intermolecular contacts in compounds (I)-(III). top

Compound	D—H···A	D—H	H···A	D···A	D—H···A
(I)	C8—H8···N1ⁱ	0.95	2.62	3.561 (2)	170
(II)	C7—H7···N1ⁱⁱ	0.95	2.75	3.678 (3)	168
	C426—H426···Cg1ⁱⁱⁱ	0.95	2.86	3.3627 (17)	114
(III)	C21—H21A···N1^iv	0.98	2.63	3.594 (3)	170

Cg1 represents the centroid of the N1/C2//C4/C4A/C8A ring.

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

Acknowledgements

JC thanks the Centro de Instrumentación Científico–Técnica of the Universidad de Jaén (UJA) and its staff for the data collection.

Funding information

Funding for this research was provided by: Vicerrectoría de Investigación y Extensión of the Industrial University of Santander (grant No. 2680 to AP); Universidad de Jaén and the Consejería de Economía, Innovación, Ciencia y Empleo (Junta de Andalucá, Spain) (award to JC).

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ISSN: 2053-2296

Volume 78| Part 10| October 2022| Pages 524-530

https://doi.org/10.1107/S2053229622008634

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

Synthesis and spectroscopic and structural characterization of three new 2-methyl-4-styryl­quinolines formed using Friedländer reactions between (2-amino­phen­yl)chalcones and acetone

1. Introduction

2. Experimental

2.1. Synthesis and crystallization

2.2. Refinement

3. Results and discussion

Supporting information

Acknowledgements

Funding information

References

research papers

Synthesis and spectroscopic and structural characterization of three new 2-methyl-4-styrylquinolines formed using Friedländer reactions between (2-aminophenyl)chalcones and acetone