4-Styryl­quino­lines from cyclo­condensation reactions between (2-amino­phen­yl)chalcones and 1,3-diketones: crystal structures and regiochemistry

Rodríguez, D.; Guerrero, S.A.; Palma, A.; Cobo, J.; Glidewell, C.

doi:10.1107/S2053229620010803

research papers

STRUCTURAL
CHEMISTRY

ISSN: 2053-2296

Volume 76| Part 9| September 2020| Pages 883-890

https://doi.org/10.1107/S2053229620010803

Open

access

4-Styrylquinolines from cyclocondensation reactions between (2-aminophenyl)chalcones and 1,3-diketones: crystal structures and regiochemistry

Diego Rodríguez,^a Sergio Andrés Guerrero,^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, Fife KY16 9ST, Scotland
^*Correspondence e-mail: cg@st-andrews.ac.uk

Edited by A. L. Spek, Utrecht University, The Netherlands (Received 3 August 2020; accepted 4 August 2020; online 13 August 2020)

Structures are reported for two matched sets of substituted 4-styrylquinolines which were prepared by the formation of the heterocyclic ring in cyclocondensation reactions between 1-(2-aminophenyl)-3-arylprop-2-en-1-ones with 1,3-dicarbonyl compounds. (E)-3-Acetyl-4-[2-(4-methoxyphenyl)ethenyl]-2-methylquinoline, C₂₁H₁₉NO₂, (I), (E)-3-acetyl-4-[2-(4-bromophenyl)ethenyl]-2-methylquinoline, C₂₀H₁₆BrNO, (II), and (E)-3-acetyl-2-methyl-4-{2-[4-(trifluoromethyl)phenyl]ethenyl}quinoline, C₂₁H₁₆F₃NO, (III), are isomorphous and in each structure the molecules are linked by a single C—H⋯O hydrogen bond to form C(6) chains. In (I), but not in (II) or (III), this is augmented by a C—H⋯π(arene) hydrogen bond to form a chain of rings; hence, (I)–(III) are not strictly isostructural. By contrast with (I)–(III), no two of ethyl (E)-4-[2-(4-methoxyphenyl)ethenyl]-2-methylquinoline-3-carboxylate, C₂₂H₂₁NO₃, (IV), ethyl (E)-4-[2-(4-bromophenyl)ethenyl]-2-methylquinoline-3-carboxylate, C₂₁H₁₈BrNO₂, (V), and ethyl (E)-2-methyl-4-{2-[4-(trifluoromethyl)phenyl]ethenyl}quinoline-3-carboxylate, C₂₂H₁₈F₃NO₂, (VI), are isomorphous. The molecules of (IV) are linked by a single C—H⋯O hydrogen bond to form C(13) chains, but cyclic centrosymmetric dimers are formed in both (V) and (VI). The dimer in (V) contains a C—H⋯π(pyridyl) hydrogen bond, while that in (VI) contains two independent C—H⋯O hydrogen bonds. Comparisons are made with some related structures, and both the regiochemistry and the mechanism of the heterocyclic ring formation are discussed.

Keywords: synthesis; cyclocondensation; quinolone; crystal structure; molecular conformation; hydrogen bonding; supramolecular assembly; regiochemistry.

CCDC references: 2021528; 2021527; 2021526; 2021525; 2021524; 2021523

1. Introduction

Compounds containing 2-styrylquinoline units have attracted interest in recent years because of their potential as anticancer (El-Sayed et al., 2018 ), anti-HIV (Polanski et al., 2002 ), antimalarial (Roberts et al., 2017 ) and antimicrobial (Cieslik et al., 2012 ) agents, as well as in the treatment of Alzheimer's dementia (Wang et al., 2015 ). By contrast, analogous compounds containing 4-styryl units have been very much less extensively investigated, probably, at least in part, because of a lack of efficient and versatile methods for their synthesis: such methods have generally been based on coupling reactions requiring the prior synthesis of haloquinolines or (haloalkyl)quinolines, combined with either harsh reaction conditions or the use of expensive heavy-metal catalysts (Omar & Hormi, 2009 ; Xia et al., 2016 ). However, a very straightforward synthesis of 4-styrylquinolines has been developed recently (Meléndez et al., 2020 ), in which the heterocyclic ring of the quinoline unit is built in situ using a cyclocondensation reaction between a 2′-aminochalcone, (A), and a 1,3-dicarbonyl compound (cf. Scheme 1). The chalcone component in this type of cyclization is readily accessible by reaction between 2′-aminoacetophenone and an aromatic aldehyde, allowing incorporation of a wide variety of substituents both in the styryl portion and at the 3-position of the quinoline nucleus. We report here the molecular structures and supramolecular assembly of two matched sets, each of three related products: the 3-acetyl derivatives, compounds (I)–(III) (Scheme 1 and Figs. 1–3 ), where X = Me, were all obtained using pentane-2,4-dione as the dicarbonyl component, while the 3-carboethoxy derivatives, compounds (IV)–(VI) (Figs. 4–6 ), where X = OEt, were all obtained using ethyl 3-oxobutanoate (ethyl acetoacetate). Compounds such as (I)–(III), containing an acetyl

group, can act as useful synthetic intermediates, as they can undergo condensation with a further substituted aldehyde to form a chalcone substituent at the 3-position, as exemplified by compound (VIII) (Scheme 2

). Such chalcones can themselves then undergo cyclocondensation reactions, for example, with a hydrazine, to form either a pyrazole, under basic conditions (Samshuddin et al., 2014

), or a reduced pyrazole ring, under acidic conditions (Jasinski et al., 2010

), or with guanidine to form a reduced pyrimidine ring (Nayak et al., 2014

), thus giving access to a rich diversity of new 4-styrylquinolin-3-yl heterocycles. In addition to reporting the molecular and supramolecular structures of compounds (I)–(VI), we also briefly consider compounds (VII) and (VIII) (Scheme 2

). These have been reported on a simple proof of constitution basis [Cambridge Structural Database (CSD; Groom et al., 2016

) refcodes MUMZEC and MUMZIG (Meléndez et al., 2020

)] but without any structure description or discussion; accordingly, we discuss here the supramolecular assembly in these two compounds.

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.

Figure 4
The molecular structure of compound (IV)

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

Figure 5
The molecular structure of compound (V)

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

Figure 6
The molecular structure of compound (VI)

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

2. Experimental

2.1. Synthesis and crystallization

Samples of compounds (I)–(VI) were prepared and crystallized following a recently published procedure (Meléndez et al., 2020).

2.2. Refinement

Crystal data, data collection and structure refinement details for compounds (I)–(VI) are summarized in Table 1. Two low-angle reflections which had been attenuated by the beam stop [100 for (I) and $[\overline{1}]$ 01 for (VI)] were omitted from the data sets before the final refinements; likewise, two bad outlier reflections (639 and 606) were removed from the data set for (IV). All H atoms were located in difference maps and subsequently treated as riding atoms in geometrically idealized positions, with C—H = 0.95 (alkenyl, aromatic and heteroaromatic), 0.98 (CH₃) or 0.99 Å (CH₂), 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. For compounds (VII) and (VIII), the published structures (Meléndez et al., 2020) were inverted and the atom labelling adjusted slightly in order to bring them into full conformity with compounds (I)–(VI) (cf. Tables 2 and 3); the modified versions of the CIFs for (VII) and (VIII) are provided in the supporting information. Examination of the structure for (VIII) using PLATON (Spek, 2020 ) showed that the unit cell contains two voids, each of volume 60 Å³ and centred at (0, $[1 \over 2]$ , 0) and ( $[1 \over 2]$ , 0, $[1 \over 2]$ ), but further examination using SQUEEZE (Spek, 2015 ) showed that these voids contained negligible electron density.

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	C₂₁H₁₉NO₂	C₂₀H₁₆BrNO	C₂₁H₁₆F₃NO
M_r	317.37	366.24	355.35
Crystal system, space group	Monoclinic, P2₁/c	Monoclinic, P2₁/c	Monoclinic, P2₁/c
a, b, c (Å)	8.2595 (4), 6.4279 (3), 31.9064 (14)	8.0849 (3), 6.6692 (2), 31.1063 (10)	8.0822 (4), 6.6567 (4), 32.1024 (17)
α, β, γ (°)	90, 93.674 (2), 90	90, 95.005 (1), 90	90, 90.576 (2), 90
V (Å³)	1690.47 (14)	1670.85 (10)	1727.05 (16)
Z	4	4	4
μ (mm⁻¹)	0.08	2.46	0.11
Crystal size (mm)	0.23 × 0.16 × 0.09	0.17 × 0.11 × 0.04	0.20 × 0.08 × 0.06

Data collection
T_min, T_max	0.947, 0.993	0.810, 0.906	0.942, 0.994
No. of measured, independent and observed [I > 2σ(I)] reflections	39800, 4197, 3528	38342, 3839, 3434	19648, 3959, 3363
R_int	0.051	0.034	0.032
(sin θ/λ)_max (Å⁻¹)	0.668	0.650	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.111, 1.06	0.030, 0.073, 1.03	0.041, 0.101, 1.04
No. of reflections	4197	3839	3959
No. of parameters	220	210	237
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.23	0.56, −0.76	0.28, −0.23

	(IV)	(V)	(VI)
Crystal data
Chemical formula	C₂₂H₂₁NO₃	C₂₁H₁₈BrNO₂	C₂₂H₁₈F₃NO₂
M_r	347.40	396.26	385.37
Crystal system, space group	Triclinic, P $[\overline{1}]$	Monoclinic, P2₁/n	Triclinic, P $[\overline{1}]$
a, b, c (Å)	9.5301 (8), 10.3513 (8), 10.3621 (8)	9.5709 (6), 10.6119 (7), 18.2074 (10)	8.7465 (10), 9.9436 (11), 11.1116 (11)
α, β, γ (°)	65.374 (3), 86.583 (3), 76.376 (3)	90, 90.939 (2), 90	105.446 (4), 99.763 (4), 97.204 (4)
V (Å³)	902.23 (13)	1849.0 (2)	903.08 (17)
Z	2	4	2
μ (mm⁻¹)	0.09	2.24	0.11
Crystal size (mm)	0.30 × 0.12 × 0.05	0.25 × 0.18 × 0.15	0.27 × 0.20 × 0.18

Data collection
T_min, T_max	0.954, 0.996	0.595, 0.715	0.954, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	44489, 4158, 3440	54534, 4588, 4098	59876, 4491, 3692
R_int	0.053	0.041	0.042
(sin θ/λ)_max (Å⁻¹)	0.650	0.667	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.128, 1.07	0.022, 0.056, 1.02	0.044, 0.120, 1.05
No. of reflections	4158	4588	4491
No. of parameters	238	228	255
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.21	0.35, −0.42	0.43, −0.43
Computer programs: APEX3 (Bruker, 2018 ), SAINT (Bruker, 2017 ), SHELXT2014 (Sheldrick, 2015a ), SHELXL2014 (Sheldrick, 2015b ) and PLATON (Spek, 2020).

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

Compound	C3—C4—C41—C42	C41—C42—C421—C422	C2—C3—C31—O31	C2—C3—C31—O32
(I)	46.40 (16)	13.78 (18)	66.18 (15)
(II)	46.8 (3)	14.8 (3)	68.2 (2)
(III)	49.0 (2)	13.0 (2)	69.52 (18)
(IV)	48.8 (2)	1.2 (3)	73.7 (2)	−104.85 (17)
(V)	51.4 (2)	10.6 (2)	−102.56 (17)	75.88 (15)
(VI)	34.8 (2)	−17.7 (2)	−99.75 (16)	76.46 (15)
(VII)	51.0 (5)	2.0 (5)	71.5 (4)
(VIII)	54.17 (19)	−4.0 (2)	−97.59 (15)

Table 3
Hydrogen bonds and short intramolecular contacts (Å, °) for compounds (I)–(VIII)

	D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
(I)	C41—H41⋯O31ⁱ	0.95	2.41	3.2527 (15)	148
	C426—H426⋯Cg3ⁱⁱ	0.95	2.77	3.5252 (13)	138
(II)	C41—H41⋯O31ⁱ	0.95	2.37	3.283 (2)	161
	C426—H426⋯Cg3ⁱⁱ	0.95	2.91	3.7071 (19)	142
(III)	C41—H41⋯O31ⁱ	0.95	2.42	3.3290 (17)	161
	C426—H426⋯Cg3ⁱⁱ	0.95	3.00	3.7621 (15)	138
(IV)	C32—H32B⋯O424ⁱⁱⁱ	0.99	2.57	3.406 (2)	142
	C423—H423⋯Cg1^iv	0.95	2.91	3.4894 (19)	120
(V)	C423—H423⋯O31^v	0.95	2.59	3.2197 (17)	124
	C426—H426⋯Cg1^iv	0.95	2.74	3.5961 (16)	151
(VI)	C41—H41⋯O31^iv	0.95	2.54	3.4922 (18)	178
	C422—H422⋯O31^iv	0.95	2.56	3.3924 (19)	146
(VII)	C41—H41⋯O31^vi	0.95	2.37	3.300 (5)	167
	C422—H422⋯O31^vi	0.95	2.57	3.506 (4)	169
	C426—H426⋯Cg4^vii	0.95	2.67	3.549 (4)	155
(VIII)	C334—H334⋯O31^viii	0.95	2.61	3.542 (2)	168
	C7—H7⋯Cg5^ix	0.95	2.93	3.6437 (16)	133
	C422—H422⋯Cg1^x	0.95	2.93	3.6300 (17)	132
Symmetry codes: (i) x, y + 1, z; (ii) −x + 1, y − $[{1\over 2}]$ , −z + $[{1\over 2}]$ ; (iii) x + 1, y, z; (iv) −x + 1, −y + 1, −z + 1; (v) −x + $[{3\over 2}]$ , y + $[{1\over 2}]$ , −z + $[{3\over 2}]$ ; (vi) x − $[{1\over 2}]$ , y, −z + $[{1\over 2}]$ ; (vii) −x + $[{3\over 2}]$ , y − $[{1\over 2}]$ , z; (viii) x − 1, y, z; (ix) x + $[{1\over 2}]$ , −y + $[{1\over 2}]$ , z − $[{1\over 2}]$ ; (x) x + $[{1\over 2}]$ , −y + $[{1\over 2}]$ , z + $[{1\over 2}]$ .

3. Results and discussion

In reactions between a chalcone of type (A) (Scheme 1) and a symmetrical 1,3-diketone, such as pentane-2,4-dione, only a single product is possible, namely, the 3-acetyl-2-methylquinoline derivative, as exemplified by compounds (I)–(III). However, a comparable reaction involving an unsymmetrical diketone, such as 1-phenylbutane-1,3-dione can give two regioisomers, such as (VII), if the amino group reacts at the acetyl carbonyl group, or the alternative (IX) if the reaction occurs at the benzoyl carbonyl group. In general, reactions with this ketone lead exclusively to the 3-benzoyl-2-methyl isomers, as exemplified by (VII), rather than to the 3-acetyl-2-phenyl alternative exemplified by (IX) (Meléndez et al., 2020), which is consistent with the greater reactivity in the nucleophilic addition reaction of acetyl groups compared with benzoyl groups (Bürgi et al., 1974 ; Katritzsky et al., 1995 ; Meléndez et al., 2020). Similarly, the reaction of a chalcone of type (A) with an unsymmetrical diketo compound, such as ethyl 3-oxobutanoate, can, in principle, give two types of product: reaction of the amino group at the acetyl carbonyl group leads to ethyl esters, as exemplified by compounds (IV)–(VI), but reaction of the amino group at the ester carbonyl group would lead to elimination of ethanol with the formation of a 2-quinolone of type (X) (Scheme 2). Again, these reactions appear to lead exclusively to the esters, as exemplified by (IV)–(VI) (Meléndez et al., 2020), consistent with the greater electrophilicity of a ketonic carbonyl group compared with an ester carbonyl group. On the other hand, 2-aryl-4-quinolones are sometimes formed as by-products arising from an intramolecular cyclization of the chalcone precursor.

Compounds (I)–(III), where X = Me and Y = OMe, Br or CF₃, respectively (Scheme 1 and Figs. 1–3 ), all crystallize in the space group P2₁/c with rather similar unit-cell dimensions (Table 1) and very similar molecular conformations (Table 2); each structure can be refined using the coordinates of one of the others as the starting point, provided due alteration is made in the substituent at atom C424 (Figs. 1–3 ). However, although there are short intermolecular C—H⋯O and C—H⋯π(arene) contacts in all three compounds, involving the same sets of atoms (Table 3), in each of compounds (II) and (III), the H⋯Cg distance is quite long and probably of marginal structural significance, whereas it can be regarded as a genuine hydrogen bond in compound (I). On this basis, compounds (I)–(III) can be regarded as isomorphous but not strictly isostructural (Acosta et al., 2009 ; Blanco et al., 2012 ). However, in the comparable series of compounds, i.e. (IV)–(VI), where X = OEt, although compounds (IV) and (VI) are both triclinic, in (IV) the inter-axial angles are all less than 90°, but in (VI) they are greater than 90°, so that these two compounds are far from being isomorphous. On the other hand, the third member of this group, compound (V), is monoclinic, so there can be no close similarities within this group.

None of the molecules of (I)–(VIII) exhibits any internal symmetry, so that they are all conformationally chiral; in each case, the reference molecule was selected as one having a positive sign for the C3—C4—C41—C42 torsion angle (Table 2), although the space groups confirm that all the compounds have crystallized as conformational racemates.

The supramolecular assembly of compounds (I)–(VI) is determined by C—H⋯O and C—H⋯π hydrogen bonds (Table 3). In each of (I)–(III), molecules which are related by translation are linked by a C—H⋯O hydrogen bond to form a C(6) (Etter, 1990 ; Etter et al., 1990 ; Bernstein et al., 1995 ) chain running parallel to the [010] direction. In the structure of (I), this is enhanced by a C—H⋯π(arene) hydrogen bond linking molecules related by the 2₁ screw axis along ( $[1 \over 2]$ , y, $[1 \over 4]$ ) to form a chain of rings (Fig. 7). However, in the structures of (II) and (III), the corresponding H⋯Cg and C⋯Cg distances are much longer than they are in (I), so that these are possibly better regarded as short adventitious contacts rather than structurally significant hydrogen bonds.

Figure 7
Part of the crystal structure of compound (I)

, showing the formation of a chain of rings along [010] built from C—H⋯O and C—H⋯π(arene) hydrogen bonds, drawn as dashed lines. For the sake of clarity, H atoms not involved in the motifs shown have been omitted.

A single C—H⋯O hydrogen bond links the molecules of compound (IV) which are related by translation into a C(13) chain running parallel to the [100] direction (Fig. 8). This structure also contains a short C—H⋯π(pyridyl) contact, but the long H⋯Cg distance and the very small C—H⋯Cg angle indicate that this is probably not structurally significant (Wood et al., 2009 ). By contrast, in the structure of compound (V), it is the C—H⋯O contact which has a very small D—H⋯A angle (Table 3), while a C—H⋯π(pyridyl) hydrogen bond links molecules which are related by inversion to form a cyclic centrosymmetric dimer (Fig. 9).

Figure 8
Part of the crystal structure of compound (IV)

, showing the formation of a C(13) chain running parallel to the [100] direction. Hydrogen bonds are drawn as dashed lines and, for the sake of clarity, H atoms bonded to those C atoms which are not involved in the motif shown have been omitted. Atoms marked with an asterisk (*) or a hash (#) are at the symmetry positions (x + 1, y, z) and (x − 1, y, z), respectively.

Figure 9
Part of the crystal structure of compound (V)

, showing the formation of a centrosymmetric dimer. Hydrogen bonds are drawn as dashed lines and, for the sake of clarity, H atoms which are not involved in the motif shown have been omitted. The atom marked with an asterisk (*) is at the symmetry position (−x + 1, −y + 1, −z + 1).

In the structure of compound (VI), there are no C—H⋯π hydrogen bonds or short intermolecular contacts. Instead two C—H⋯O hydrogen bonds combine to link inversion-related pairs of molecules into centrosymmetric dimers. The hydrogen bonds involving atoms of type C41 form an R₂²(12) ring, while those involving atoms of type C422 generate an R₂²(18) ring (Fig. 10).

Figure 10
Part of the crystal structure of compound (VI)

, showing the formation of a centrosymmetric dimer. Hydrogen bonds are drawn as dashed lines and, for the sake of clarity, H atoms which are not involved in the motif shown have been omitted. Atoms marked with an asterisk (*) are at the symmetry position (−x + 1, −y + 1, −z + 1).

We also discuss here the supramolecular assembly of compounds (VII) and (VIII), which, as noted above (§1, Introduction), have been reported on a simple proof of constitution basis, without discussion (Meléndez et al., 2020). The assembly in (VII) in the space group Pbcn is based upon two C—H⋯O hydrogen bonds and one C—H⋯π(arene) hydrogen bond (Table 3). The two C—H⋯O hydrogen bonds link molecules which are related by the a-glide plane at z = $[1 \over 4]$ to form a C(6)C(9)[R₂¹(7)] chain of rings running parallel to the [100] direction (Fig. 11). In addition, the structure of (VII) contains a C—H⋯π(arene) hydrogen bond which links molecules which are related by the b-glide plane at x = $[3 \over 4]$ to form a chain running parallel to the [010] direction (Fig. 12). The combination of the chain motifs along [100] and [010] generates a complex sheet lying parallel to (001) in the domain 0 < z < $[1 \over 2]$ ; a second sheet of this type, related to the first by inversion, lies in the domain $[1 \over 2]$ < z < 1.0, but there are no direction-specific interactions between adjacent sheets. Even the shortest intermolecular contacts (Table 3) in chalcone (VIII) have H⋯A distances which are probably too long for these contacts to be regarded as structurally significant.

Figure 11
Part of the crystal structure of compound (VII), showing the formation of a C(6)C(9)[R₂¹(7)] chain of rings running parallel to the [100] direction. Hydrogen bonds are drawn as dashed lines and, for the sake of clarity, H atoms which are not involved in the motif shown have been omitted.

Figure 12
Part of the crystal structure of compound (VII), showing the formation of a chain built from C—H⋯π(arene) hydrogen bonds, drawn as dashed lines, running parallel to the [010] direction. For the sake of clarity, H atoms which are not involved in the motif shown have been omitted.

The structures of several simple 2-styrylquinolines have been published, including those of the unsubstituted 2-styrylquinoline itself (Valle et al., 1986 ), and of several analogues carrying simple substituents in the phenyl ring (Kuz'mina et al., 2012 ). In addition, structures have been reported for a number of salts derived from 2-styrylquinolines (Kobkeatthawin et al., 2008 , 2009 ; Chantrapromma et al., 2008 , 2014 ; Fun et al., 2013 ). For all of these compounds, the styryl group was introduced into a preformed quinoline nucleus. 8-Styrylquinoline and its 4-phenylstyryl analogue, whose structures have also been reported (Sharma et al., 2015 ), were prepared using a rhodium-catalysed coupling reaction between quinoline N-oxide and the styrene component. Despite the substantial number of structure reports involving 2-styrylquinolines and their derivatives, there are no reports in the CSD of 4-styrylquinolines other than the two examples discussed above, i.e. compounds (VII) and (VIII) (CSD refcodes MUMZEC and MUMZIG, respectively; Meléndez et al., 2020).

Supporting information

CCDC references: 2021528; 2021527; 2021526; 2021525; 2021524; 2021523

Crystal structure: contains datablocks global, I, II, III, IV, V, VI. DOI: https://doi.org/10.1107/S2053229620010803/sk3755sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2053229620010803/sk3755Isup2.hkl

Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S2053229620010803/sk3755IIsup3.hkl

Structure factors: contains datablock III. DOI: https://doi.org/10.1107/S2053229620010803/sk3755IIIsup4.hkl

Structure factors: contains datablock IV. DOI: https://doi.org/10.1107/S2053229620010803/sk3755IVsup5.hkl

Structure factors: contains datablock V. DOI: https://doi.org/10.1107/S2053229620010803/sk3755Vsup6.hkl

Structure factors: contains datablock VI. DOI: https://doi.org/10.1107/S2053229620010803/sk3755VIsup7.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2053229620010803/sk3755Isup8.cml

Supporting information file. DOI: https://doi.org/10.1107/S2053229620010803/sk3755IIsup9.cml

Supporting information file. DOI: https://doi.org/10.1107/S2053229620010803/sk3755IIIsup10.cml

Supporting information file. DOI: https://doi.org/10.1107/S2053229620010803/sk3755IVsup11.cml

Supporting information file. DOI: https://doi.org/10.1107/S2053229620010803/sk3755Vsup12.cml

Supporting information file. DOI: https://doi.org/10.1107/S2053229620010803/sk3755VIsup13.cml

Modified versions of the CIFs for (VII) and (VIII). DOI: https://doi.org/10.1107/S2053229620010803/sk3755sup14.cif

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)-3-Acetyl-4-[2-(4-methoxyphenyl)ethenyl]-2-methylquinoline (I) top

Crystal data top

C₂₁H₁₉NO₂	F(000) = 672
M_r = 317.37	D_x = 1.247 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.2595 (4) Å	Cell parameters from 4198 reflections
b = 6.4279 (3) Å	θ = 2.5–28.3°
c = 31.9064 (14) Å	µ = 0.08 mm⁻¹
β = 93.674 (2)°	T = 100 K
V = 1690.47 (14) Å³	Plate, yellow
Z = 4	0.23 × 0.16 × 0.09 mm

Data collection top

Bruker D8 Venture diffractometer	4197 independent reflections
Radiation source: INCOATEC high brilliance microfocus sealed tube	3528 reflections with I > 2σ(I)
Multilayer mirror monochromator	R_int = 0.051
φ and ω scans	θ_max = 28.3°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2016)	h = −11→11
T_min = 0.947, T_max = 0.993	k = −8→8
39800 measured reflections	l = −42→40

Refinement top

Refinement on F²	Primary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.040	H-atom parameters constrained
wR(F²) = 0.111	w = 1/[σ²(F_o²) + (0.0488P)² + 0.6947P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
4197 reflections	Δρ_max = 0.33 e Å⁻³
220 parameters	Δρ_min = −0.23 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	0.22600 (12)	0.50352 (15)	0.46800 (3)	0.0187 (2)
C2	0.35344 (13)	0.40197 (17)	0.45582 (3)	0.0183 (2)
C3	0.44411 (13)	0.47008 (17)	0.42158 (3)	0.0170 (2)
C4	0.39728 (13)	0.64671 (17)	0.39940 (3)	0.0167 (2)
C4A	0.25816 (13)	0.75745 (17)	0.41187 (3)	0.0170 (2)
C5	0.19665 (15)	0.93792 (19)	0.39100 (4)	0.0220 (2)
H5	0.2493	0.9915	0.3677	0.026*
C6	0.06173 (16)	1.0358 (2)	0.40417 (4)	0.0256 (3)
H6	0.0204	1.1553	0.3896	0.031*
C7	−0.01623 (15)	0.9608 (2)	0.43914 (4)	0.0247 (3)
H7	−0.1088	1.0313	0.4482	0.030*
C8	0.04033 (14)	0.78703 (19)	0.46010 (4)	0.0209 (2)
H8	−0.0127	0.7380	0.4838	0.025*
C8A	0.17774 (13)	0.67992 (17)	0.44663 (3)	0.0171 (2)
C21	0.40445 (16)	0.21170 (19)	0.48070 (4)	0.0238 (2)
H21A	0.3370	0.1977	0.5047	0.036*
H21B	0.5185	0.2251	0.4908	0.036*
H21C	0.3911	0.0883	0.4628	0.036*
C31	0.59731 (14)	0.35584 (18)	0.41244 (3)	0.0203 (2)
O31	0.59378 (12)	0.17673 (14)	0.40028 (3)	0.0326 (2)
C32	0.75319 (14)	0.4693 (2)	0.42241 (4)	0.0245 (3)
H32A	0.7811	0.4627	0.4527	0.037*
H32B	0.7409	0.6150	0.4137	0.037*
H32C	0.8397	0.4045	0.4073	0.037*
C41	0.48647 (13)	0.72134 (18)	0.36375 (3)	0.0185 (2)
H41	0.5124	0.8651	0.3625	0.022*
C42	0.53271 (13)	0.59664 (18)	0.33313 (3)	0.0179 (2)
H42	0.5019	0.4545	0.3345	0.021*
C421	0.62670 (13)	0.65888 (18)	0.29759 (3)	0.0176 (2)
C422	0.70887 (14)	0.84777 (18)	0.29572 (3)	0.0202 (2)
H422	0.7091	0.9402	0.3190	0.024*
C423	0.79067 (14)	0.90422 (19)	0.26062 (4)	0.0211 (2)
H423	0.8458	1.0338	0.2599	0.025*
C424	0.79091 (14)	0.76872 (19)	0.22647 (3)	0.0206 (2)
C425	0.71394 (15)	0.57636 (19)	0.22835 (4)	0.0226 (2)
H425	0.7164	0.4823	0.2054	0.027*
C426	0.63392 (14)	0.52220 (19)	0.26355 (3)	0.0200 (2)
H426	0.5830	0.3900	0.2647	0.024*
O424	0.86368 (11)	0.80822 (15)	0.18996 (3)	0.0275 (2)
C427	0.93382 (16)	1.0093 (2)	0.18527 (4)	0.0274 (3)
H47A	0.8511	1.1163	0.1886	0.041*
H47B	0.9754	1.0211	0.1573	0.041*
H47C	1.0231	1.0286	0.2067	0.041*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0202 (5)	0.0183 (5)	0.0177 (4)	−0.0008 (4)	0.0010 (3)	0.0008 (4)
C2	0.0204 (5)	0.0159 (5)	0.0182 (5)	−0.0009 (4)	−0.0008 (4)	0.0005 (4)
C3	0.0172 (5)	0.0161 (5)	0.0178 (5)	0.0008 (4)	0.0006 (4)	−0.0020 (4)
C4	0.0185 (5)	0.0163 (5)	0.0154 (5)	0.0009 (4)	0.0019 (4)	−0.0019 (4)
C4A	0.0190 (5)	0.0171 (5)	0.0150 (5)	0.0015 (4)	0.0014 (4)	−0.0015 (4)
C5	0.0280 (6)	0.0223 (6)	0.0162 (5)	0.0056 (5)	0.0057 (4)	0.0025 (4)
C6	0.0292 (6)	0.0251 (6)	0.0231 (6)	0.0098 (5)	0.0044 (5)	0.0044 (5)
C7	0.0219 (6)	0.0271 (6)	0.0257 (6)	0.0075 (5)	0.0059 (4)	0.0000 (5)
C8	0.0194 (5)	0.0246 (6)	0.0192 (5)	0.0002 (4)	0.0044 (4)	−0.0002 (4)
C8A	0.0176 (5)	0.0178 (5)	0.0157 (5)	−0.0005 (4)	0.0006 (4)	−0.0011 (4)
C21	0.0295 (6)	0.0185 (5)	0.0234 (6)	0.0028 (5)	0.0013 (5)	0.0048 (4)
C31	0.0237 (6)	0.0188 (5)	0.0185 (5)	0.0046 (4)	0.0016 (4)	0.0004 (4)
O31	0.0335 (5)	0.0205 (4)	0.0437 (6)	0.0063 (4)	0.0013 (4)	−0.0083 (4)
C32	0.0204 (6)	0.0273 (6)	0.0259 (6)	0.0038 (5)	0.0030 (4)	−0.0002 (5)
C41	0.0201 (5)	0.0176 (5)	0.0180 (5)	0.0019 (4)	0.0030 (4)	0.0013 (4)
C42	0.0176 (5)	0.0182 (5)	0.0178 (5)	0.0009 (4)	0.0009 (4)	−0.0001 (4)
C421	0.0166 (5)	0.0197 (5)	0.0164 (5)	0.0025 (4)	0.0015 (4)	−0.0011 (4)
C422	0.0205 (5)	0.0215 (6)	0.0188 (5)	0.0011 (4)	0.0030 (4)	−0.0044 (4)
C423	0.0205 (5)	0.0211 (5)	0.0220 (5)	−0.0023 (4)	0.0032 (4)	−0.0025 (4)
C424	0.0194 (5)	0.0256 (6)	0.0173 (5)	0.0007 (4)	0.0042 (4)	−0.0003 (4)
C425	0.0264 (6)	0.0244 (6)	0.0173 (5)	−0.0020 (5)	0.0043 (4)	−0.0055 (4)
C426	0.0206 (5)	0.0205 (5)	0.0189 (5)	−0.0010 (4)	0.0018 (4)	−0.0029 (4)
O424	0.0341 (5)	0.0297 (5)	0.0199 (4)	−0.0070 (4)	0.0109 (3)	−0.0027 (3)
C427	0.0276 (6)	0.0314 (7)	0.0240 (6)	−0.0065 (5)	0.0066 (5)	0.0027 (5)

Geometric parameters (Å, º) top

N1—C2	1.3181 (15)	C32—H32A	0.9800
N1—C8A	1.3692 (14)	C32—H32B	0.9800
C2—C3	1.4319 (15)	C32—H32C	0.9800
C2—C21	1.5036 (16)	C41—C42	1.3382 (15)
C3—C4	1.3800 (15)	C41—H41	0.9500
C3—C31	1.5076 (15)	C42—C421	1.4701 (15)
C4—C4A	1.4296 (15)	C42—H42	0.9500
C4—C41	1.4746 (15)	C421—C422	1.3941 (16)
C4A—C5	1.4157 (16)	C421—C426	1.4012 (15)
C4A—C8A	1.4190 (15)	C422—C423	1.3926 (16)
C5—C6	1.3691 (16)	C422—H422	0.9500
C5—H5	0.9500	C423—C424	1.3952 (16)
C6—C7	1.4087 (17)	C423—H423	0.9500
C6—H6	0.9500	C424—O424	1.3684 (13)
C7—C8	1.3685 (17)	C424—C425	1.3934 (17)
C7—H7	0.9500	C425—C426	1.3837 (15)
C8—C8A	1.4176 (15)	C425—H425	0.9500
C8—H8	0.9500	C426—H426	0.9500
C21—H21A	0.9800	O424—C427	1.4282 (15)
C21—H21B	0.9800	C427—H47A	0.9800
C21—H21C	0.9800	C427—H47B	0.9800
C31—O31	1.2147 (15)	C427—H47C	0.9800
C31—C32	1.4959 (17)

C2—N1—C8A	118.41 (9)	C31—C32—H32A	109.5
N1—C2—C3	122.69 (10)	C31—C32—H32B	109.5
N1—C2—C21	116.69 (10)	H32A—C32—H32B	109.5
C3—C2—C21	120.59 (10)	C31—C32—H32C	109.5
C4—C3—C2	119.97 (10)	H32A—C32—H32C	109.5
C4—C3—C31	120.84 (10)	H32B—C32—H32C	109.5
C2—C3—C31	119.03 (10)	C42—C41—C4	123.26 (11)
C3—C4—C4A	118.09 (10)	C42—C41—H41	118.4
C3—C4—C41	121.72 (10)	C4—C41—H41	118.4
C4A—C4—C41	120.19 (10)	C41—C42—C421	126.13 (11)
C5—C4A—C8A	118.92 (10)	C41—C42—H42	116.9
C5—C4A—C4	123.21 (10)	C421—C42—H42	116.9
C8A—C4A—C4	117.87 (10)	C422—C421—C426	117.90 (10)
C6—C5—C4A	120.45 (11)	C422—C421—C42	123.54 (10)
C6—C5—H5	119.8	C426—C421—C42	118.56 (10)
C4A—C5—H5	119.8	C423—C422—C421	121.59 (10)
C5—C6—C7	120.54 (11)	C423—C422—H422	119.2
C5—C6—H6	119.7	C421—C422—H422	119.2
C7—C6—H6	119.7	C422—C423—C424	119.38 (11)
C8—C7—C6	120.49 (11)	C422—C423—H423	120.3
C8—C7—H7	119.8	C424—C423—H423	120.3
C6—C7—H7	119.8	O424—C424—C425	115.33 (10)
C7—C8—C8A	120.20 (10)	O424—C424—C423	124.88 (11)
C7—C8—H8	119.9	C425—C424—C423	119.79 (10)
C8A—C8—H8	119.9	C426—C425—C424	120.08 (11)
N1—C8A—C8	117.67 (10)	C426—C425—H425	120.0
N1—C8A—C4A	122.96 (10)	C424—C425—H425	120.0
C8—C8A—C4A	119.37 (10)	C425—C426—C421	121.18 (11)
C2—C21—H21A	109.5	C425—C426—H426	119.4
C2—C21—H21B	109.5	C421—C426—H426	119.4
H21A—C21—H21B	109.5	C424—O424—C427	117.40 (9)
C2—C21—H21C	109.5	O424—C427—H47A	109.5
H21A—C21—H21C	109.5	O424—C427—H47B	109.5
H21B—C21—H21C	109.5	H47A—C427—H47B	109.5
O31—C31—C32	122.18 (11)	O424—C427—H47C	109.5
O31—C31—C3	121.35 (11)	H47A—C427—H47C	109.5
C32—C31—C3	116.30 (10)	H47B—C427—H47C	109.5

C8A—N1—C2—C3	0.77 (16)	C4—C4A—C8A—N1	−1.07 (16)
C8A—N1—C2—C21	178.74 (10)	C5—C4A—C8A—C8	−1.30 (16)
N1—C2—C3—C4	−1.17 (17)	C4—C4A—C8A—C8	179.38 (10)
C21—C2—C3—C4	−179.06 (10)	C4—C3—C31—O31	−118.43 (13)
N1—C2—C3—C31	174.26 (10)	C2—C3—C31—O31	66.18 (15)
C21—C2—C3—C31	−3.63 (16)	C4—C3—C31—C32	66.26 (14)
C2—C3—C4—C4A	0.39 (16)	C2—C3—C31—C32	−109.13 (12)
C31—C3—C4—C4A	−174.96 (10)	C3—C4—C41—C42	46.40 (16)
C2—C3—C4—C41	−179.53 (10)	C4A—C4—C41—C42	−133.52 (12)
C31—C3—C4—C41	5.12 (16)	C4—C41—C42—C421	−177.66 (10)
C3—C4—C4A—C5	−178.64 (11)	C41—C42—C421—C422	13.78 (18)
C41—C4—C4A—C5	1.29 (17)	C41—C42—C421—C426	−165.87 (11)
C3—C4—C4A—C8A	0.65 (15)	C426—C421—C422—C423	2.48 (17)
C41—C4—C4A—C8A	−179.43 (10)	C42—C421—C422—C423	−177.17 (11)
C8A—C4A—C5—C6	−0.01 (18)	C421—C422—C423—C424	−0.12 (18)
C4—C4A—C5—C6	179.27 (12)	C422—C423—C424—O424	178.54 (11)
C4A—C5—C6—C7	1.2 (2)	C422—C423—C424—C425	−1.99 (18)
C5—C6—C7—C8	−1.0 (2)	O424—C424—C425—C426	−178.81 (11)
C6—C7—C8—C8A	−0.36 (19)	C423—C424—C425—C426	1.68 (18)
C2—N1—C8A—C8	179.91 (10)	C424—C425—C426—C421	0.77 (18)
C2—N1—C8A—C4A	0.36 (16)	C422—C421—C426—C425	−2.80 (17)
C7—C8—C8A—N1	−178.08 (11)	C42—C421—C426—C425	176.87 (11)
C7—C8—C8A—C4A	1.49 (17)	C425—C424—O424—C427	175.49 (11)
C5—C4A—C8A—N1	178.24 (10)	C423—C424—O424—C427	−5.02 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C41—H41···O31ⁱ	0.95	2.41	3.2527 (15)	148
C426—H426···Cg3ⁱⁱ	0.95	2.77	3.5252 (13)	138

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

(E)-3-Acetyl-4-[2-(4-bromophenyl)ethenyl]-2-methylquinoline (II) top

Crystal data top

C₂₀H₁₆BrNO	F(000) = 744
M_r = 366.24	D_x = 1.456 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.0849 (3) Å	Cell parameters from 3839 reflections
b = 6.6692 (2) Å	θ = 2.5–27.5°
c = 31.1063 (10) Å	µ = 2.46 mm⁻¹
β = 95.005 (1)°	T = 100 K
V = 1670.85 (10) Å³	Plate, yellow
Z = 4	0.17 × 0.11 × 0.04 mm

Data collection top

Bruker D8 Venture diffractometer	3839 independent reflections
Radiation source: INCOATEC high brilliance microfocus sealed tube	3434 reflections with I > 2σ(I)
Multilayer mirror monochromator	R_int = 0.034
φ and ω scans	θ_max = 27.5°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2016)	h = −10→10
T_min = 0.810, T_max = 0.906	k = −8→8
38342 measured reflections	l = −39→40

Refinement top

Refinement on F²	Primary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.030	H-atom parameters constrained
wR(F²) = 0.073	w = 1/[σ²(F_o²) + (0.0294P)² + 1.5332P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
3839 reflections	Δρ_max = 0.56 e Å⁻³
210 parameters	Δρ_min = −0.76 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	0.22878 (18)	0.4980 (2)	0.46764 (5)	0.0216 (3)
C2	0.3566 (2)	0.4009 (2)	0.45402 (5)	0.0214 (3)
C3	0.4453 (2)	0.4719 (2)	0.41918 (5)	0.0198 (3)
C4	0.3970 (2)	0.6464 (2)	0.39805 (5)	0.0198 (3)
C4A	0.2553 (2)	0.7499 (2)	0.41163 (5)	0.0211 (3)
C5	0.1897 (2)	0.9251 (3)	0.39104 (6)	0.0314 (4)
H5	0.2403	0.9788	0.3671	0.038*
C6	0.0535 (3)	1.0184 (3)	0.40534 (7)	0.0358 (5)
H6	0.0093	1.1347	0.3909	0.043*
C7	−0.0209 (2)	0.9429 (3)	0.44112 (6)	0.0302 (4)
H7	−0.1138	1.0101	0.4511	0.036*
C8	0.0395 (2)	0.7731 (3)	0.46174 (6)	0.0249 (3)
H8	−0.0110	0.7237	0.4861	0.030*
C8A	0.1770 (2)	0.6713 (2)	0.44684 (5)	0.0203 (3)
C21	0.4107 (2)	0.2140 (3)	0.47846 (6)	0.0290 (4)
H21A	0.3457	0.1989	0.5034	0.043*
H21B	0.5288	0.2242	0.4884	0.043*
H21C	0.3927	0.0972	0.4595	0.043*
C31	0.5978 (2)	0.3597 (3)	0.40803 (6)	0.0248 (3)
O31	0.58723 (19)	0.1923 (2)	0.39267 (5)	0.0402 (3)
C32	0.7612 (2)	0.4597 (3)	0.41940 (7)	0.0315 (4)
H32A	0.7915	0.4466	0.4505	0.047*
H32B	0.7527	0.6021	0.4117	0.047*
H32C	0.8465	0.3961	0.4035	0.047*
C41	0.4876 (2)	0.7319 (3)	0.36336 (5)	0.0221 (3)
H41	0.5115	0.8713	0.3646	0.026*
C42	0.5388 (2)	0.6286 (3)	0.33029 (5)	0.0218 (3)
H42	0.5101	0.4906	0.3282	0.026*
C421	0.63654 (19)	0.7121 (3)	0.29676 (5)	0.0223 (3)
C422	0.7176 (2)	0.8969 (3)	0.30115 (6)	0.0263 (4)
H422	0.7123	0.9718	0.3270	0.032*
C423	0.8056 (2)	0.9731 (3)	0.26847 (6)	0.0298 (4)
H423	0.8603	1.0989	0.2717	0.036*
C424	0.8123 (2)	0.8621 (3)	0.23090 (6)	0.0303 (4)
Br42	0.93043 (2)	0.96822 (4)	0.18577 (2)	0.04244 (9)
C425	0.7361 (2)	0.6784 (4)	0.22581 (6)	0.0368 (5)
H425	0.7429	0.6037	0.2000	0.044*
C426	0.6488 (2)	0.6033 (3)	0.25888 (6)	0.0304 (4)
H426	0.5967	0.4758	0.2556	0.037*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0235 (7)	0.0197 (7)	0.0218 (7)	−0.0007 (5)	0.0040 (5)	0.0022 (5)
C2	0.0252 (8)	0.0163 (7)	0.0228 (8)	−0.0003 (6)	0.0019 (6)	0.0013 (6)
C3	0.0221 (7)	0.0167 (7)	0.0209 (8)	0.0011 (6)	0.0025 (6)	−0.0029 (6)
C4	0.0234 (7)	0.0181 (7)	0.0183 (7)	0.0017 (6)	0.0035 (6)	−0.0014 (6)
C4A	0.0248 (8)	0.0206 (8)	0.0183 (7)	0.0039 (6)	0.0037 (6)	0.0008 (6)
C5	0.0389 (10)	0.0314 (10)	0.0257 (9)	0.0141 (8)	0.0128 (7)	0.0104 (7)
C6	0.0420 (11)	0.0338 (10)	0.0329 (10)	0.0195 (9)	0.0106 (8)	0.0112 (8)
C7	0.0282 (9)	0.0318 (10)	0.0317 (9)	0.0111 (7)	0.0095 (7)	0.0020 (8)
C8	0.0243 (8)	0.0280 (9)	0.0231 (8)	0.0017 (7)	0.0068 (6)	0.0004 (7)
C8A	0.0220 (7)	0.0196 (8)	0.0193 (7)	0.0005 (6)	0.0024 (6)	0.0001 (6)
C21	0.0359 (9)	0.0205 (8)	0.0312 (9)	0.0040 (7)	0.0066 (7)	0.0076 (7)
C31	0.0309 (9)	0.0193 (8)	0.0250 (8)	0.0067 (7)	0.0076 (7)	0.0026 (6)
O31	0.0482 (8)	0.0202 (7)	0.0543 (9)	0.0054 (6)	0.0170 (7)	−0.0086 (6)
C32	0.0252 (9)	0.0346 (10)	0.0351 (10)	0.0085 (7)	0.0041 (7)	0.0015 (8)
C41	0.0259 (8)	0.0195 (8)	0.0215 (8)	0.0035 (6)	0.0058 (6)	0.0022 (6)
C42	0.0205 (7)	0.0239 (8)	0.0212 (8)	0.0009 (6)	0.0025 (6)	−0.0013 (6)
C421	0.0182 (7)	0.0305 (9)	0.0184 (8)	0.0026 (6)	0.0026 (6)	−0.0014 (6)
C422	0.0247 (8)	0.0319 (9)	0.0227 (8)	0.0003 (7)	0.0046 (6)	−0.0039 (7)
C423	0.0253 (8)	0.0352 (10)	0.0295 (9)	−0.0019 (7)	0.0059 (7)	0.0019 (8)
C424	0.0198 (8)	0.0518 (12)	0.0200 (8)	0.0001 (8)	0.0054 (6)	0.0042 (8)
Br42	0.03101 (11)	0.07124 (17)	0.02652 (11)	−0.00315 (9)	0.01070 (8)	0.01007 (9)
C425	0.0309 (9)	0.0599 (14)	0.0205 (9)	−0.0071 (9)	0.0063 (7)	−0.0119 (9)
C426	0.0267 (8)	0.0405 (11)	0.0246 (9)	−0.0067 (8)	0.0053 (7)	−0.0100 (8)

Geometric parameters (Å, º) top

N1—C2	1.321 (2)	C31—O31	1.214 (2)
N1—C8A	1.372 (2)	C31—C32	1.495 (3)
C2—C3	1.431 (2)	C32—H32A	0.9800
C2—C21	1.505 (2)	C32—H32B	0.9800
C3—C4	1.377 (2)	C32—H32C	0.9800
C3—C31	1.509 (2)	C41—C42	1.334 (2)
C4—C4A	1.432 (2)	C41—H41	0.9500
C4—C41	1.471 (2)	C42—C421	1.472 (2)
C4A—C8A	1.413 (2)	C42—H42	0.9500
C4A—C5	1.413 (2)	C421—C426	1.395 (2)
C5—C6	1.372 (3)	C421—C422	1.397 (3)
C5—H5	0.9500	C422—C423	1.387 (3)
C6—C7	1.404 (3)	C422—H422	0.9500
C6—H6	0.9500	C423—C424	1.388 (3)
C7—C8	1.371 (3)	C423—H423	0.9500
C7—H7	0.9500	C424—C425	1.375 (3)
C8—C8A	1.415 (2)	C424—Br42	1.9018 (17)
C8—H8	0.9500	C425—C426	1.390 (3)
C21—H21A	0.9800	C425—H425	0.9500
C21—H21B	0.9800	C426—H426	0.9500
C21—H21C	0.9800

C2—N1—C8A	118.51 (14)	O31—C31—C32	122.29 (16)
N1—C2—C3	122.57 (15)	O31—C31—C3	121.02 (17)
N1—C2—C21	116.44 (15)	C32—C31—C3	116.59 (15)
C3—C2—C21	120.94 (15)	C31—C32—H32A	109.5
C4—C3—C2	120.10 (15)	C31—C32—H32B	109.5
C4—C3—C31	120.88 (15)	H32A—C32—H32B	109.5
C2—C3—C31	118.92 (14)	C31—C32—H32C	109.5
C3—C4—C4A	117.88 (15)	H32A—C32—H32C	109.5
C3—C4—C41	122.63 (14)	H32B—C32—H32C	109.5
C4A—C4—C41	119.47 (14)	C42—C41—C4	125.02 (16)
C8A—C4A—C5	118.84 (15)	C42—C41—H41	117.5
C8A—C4A—C4	118.27 (15)	C4—C41—H41	117.5
C5—C4A—C4	122.89 (15)	C41—C42—C421	124.98 (16)
C6—C5—C4A	120.53 (17)	C41—C42—H42	117.5
C6—C5—H5	119.7	C421—C42—H42	117.5
C4A—C5—H5	119.7	C426—C421—C422	118.32 (16)
C5—C6—C7	120.41 (17)	C426—C421—C42	118.94 (16)
C5—C6—H6	119.8	C422—C421—C42	122.74 (15)
C7—C6—H6	119.8	C423—C422—C421	121.18 (17)
C8—C7—C6	120.49 (16)	C423—C422—H422	119.4
C8—C7—H7	119.8	C421—C422—H422	119.4
C6—C7—H7	119.8	C422—C423—C424	118.80 (18)
C7—C8—C8A	120.09 (16)	C422—C423—H423	120.6
C7—C8—H8	120.0	C424—C423—H423	120.6
C8A—C8—H8	120.0	C425—C424—C423	121.48 (17)
N1—C8A—C4A	122.63 (15)	C425—C424—Br42	119.71 (14)
N1—C8A—C8	117.77 (15)	C423—C424—Br42	118.81 (15)
C4A—C8A—C8	119.59 (15)	C424—C425—C426	119.16 (17)
C2—C21—H21A	109.5	C424—C425—H425	120.4
C2—C21—H21B	109.5	C426—C425—H425	120.4
H21A—C21—H21B	109.5	C425—C426—C421	121.04 (18)
C2—C21—H21C	109.5	C425—C426—H426	119.5
H21A—C21—H21C	109.5	C421—C426—H426	119.5
H21B—C21—H21C	109.5

C8A—N1—C2—C3	1.5 (2)	C5—C4A—C8A—C8	−2.4 (2)
C8A—N1—C2—C21	178.81 (15)	C4—C4A—C8A—C8	178.33 (15)
N1—C2—C3—C4	−0.9 (3)	C7—C8—C8A—N1	−177.65 (16)
C21—C2—C3—C4	−178.04 (16)	C7—C8—C8A—C4A	2.3 (3)
N1—C2—C3—C31	175.33 (15)	C4—C3—C31—O31	−115.6 (2)
C21—C2—C3—C31	−1.8 (2)	C2—C3—C31—O31	68.2 (2)
C2—C3—C4—C4A	−1.1 (2)	C4—C3—C31—C32	68.1 (2)
C31—C3—C4—C4A	−177.20 (15)	C2—C3—C31—C32	−108.09 (18)
C2—C3—C4—C41	177.13 (15)	C3—C4—C41—C42	46.8 (3)
C31—C3—C4—C41	1.0 (2)	C4A—C4—C41—C42	−135.02 (18)
C3—C4—C4A—C8A	2.2 (2)	C4—C41—C42—C421	−176.86 (15)
C41—C4—C4A—C8A	−176.01 (15)	C41—C42—C421—C426	−165.04 (17)
C3—C4—C4A—C5	−176.96 (17)	C41—C42—C421—C422	14.8 (3)
C41—C4—C4A—C5	4.8 (3)	C426—C421—C422—C423	1.2 (3)
C8A—C4A—C5—C6	0.7 (3)	C42—C421—C422—C423	−178.57 (16)
C4—C4A—C5—C6	179.93 (19)	C421—C422—C423—C424	0.0 (3)
C4A—C5—C6—C7	1.1 (3)	C422—C423—C424—C425	−1.0 (3)
C5—C6—C7—C8	−1.2 (3)	C422—C423—C424—Br42	179.13 (14)
C6—C7—C8—C8A	−0.5 (3)	C423—C424—C425—C426	0.7 (3)
C2—N1—C8A—C4A	−0.2 (2)	Br42—C424—C425—C426	−179.40 (15)
C2—N1—C8A—C8	179.77 (15)	C424—C425—C426—C421	0.6 (3)
C5—C4A—C8A—N1	177.56 (16)	C422—C421—C426—C425	−1.5 (3)
C4—C4A—C8A—N1	−1.7 (2)	C42—C421—C426—C425	178.30 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C41—H41···O31ⁱ	0.95	2.37	3.283 (2)	161
C426—H426···Cg3ⁱⁱ	0.95	2.91	3.7071 (19)	142

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

(E)-3-Acetyl-2-methyl-4-{2-[4-(trifluoromethyl)phenyl]ethenyl}quinoline (III) top

Crystal data top

C₂₁H₁₆F₃NO	F(000) = 736
M_r = 355.35	D_x = 1.367 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.0822 (4) Å	Cell parameters from 3961 reflections
b = 6.6567 (4) Å	θ = 2.5–27.5°
c = 32.1024 (17) Å	µ = 0.11 mm⁻¹
β = 90.576 (2)°	T = 100 K
V = 1727.05 (16) Å³	Needle, colourless
Z = 4	0.20 × 0.08 × 0.06 mm

Data collection top

Bruker D8 Venture diffractometer	3959 independent reflections
Radiation source: INCOATEC high brilliance microfocus sealed tube	3363 reflections with I > 2σ(I)
Multilayer mirror monochromator	R_int = 0.032
φ and ω scans	θ_max = 27.5°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2016)	h = −10→10
T_min = 0.942, T_max = 0.994	k = −8→8
19648 measured reflections	l = −41→40

Refinement top

Refinement on F²	Primary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.041	H-atom parameters constrained
wR(F²) = 0.101	w = 1/[σ²(F_o²) + (0.039P)² + 0.8719P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
3959 reflections	Δρ_max = 0.28 e Å⁻³
237 parameters	Δρ_min = −0.23 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	0.24277 (14)	0.49703 (17)	0.46953 (3)	0.0222 (2)
C2	0.37353 (17)	0.40329 (19)	0.45511 (4)	0.0214 (3)
C3	0.46663 (16)	0.47574 (19)	0.42048 (4)	0.0198 (3)
C4	0.41905 (16)	0.65014 (19)	0.40063 (4)	0.0200 (3)
C4A	0.27453 (17)	0.7513 (2)	0.41515 (4)	0.0213 (3)
C5	0.2095 (2)	0.9254 (2)	0.39603 (5)	0.0312 (3)
H5	0.2639	0.9819	0.3727	0.037*
C6	0.0690 (2)	1.0136 (3)	0.41073 (5)	0.0382 (4)
H6	0.0251	1.1291	0.3972	0.046*
C7	−0.01102 (19)	0.9344 (2)	0.44580 (5)	0.0334 (3)
H7	−0.1075	0.9982	0.4561	0.040*
C8	0.04868 (17)	0.7666 (2)	0.46520 (4)	0.0263 (3)
H8	−0.0056	0.7150	0.4890	0.032*
C8A	0.19136 (16)	0.6693 (2)	0.44989 (4)	0.0207 (3)
C21	0.42652 (19)	0.2158 (2)	0.47786 (5)	0.0287 (3)
H21A	0.3609	0.2007	0.5032	0.043*
H21B	0.5440	0.2258	0.4854	0.043*
H21C	0.4091	0.0988	0.4598	0.043*
C31	0.62124 (18)	0.3660 (2)	0.40773 (4)	0.0248 (3)
O31	0.61447 (15)	0.20068 (16)	0.39209 (4)	0.0390 (3)
C32	0.78127 (18)	0.4677 (2)	0.41812 (5)	0.0320 (3)
H32A	0.8021	0.4591	0.4482	0.048*
H32B	0.7752	0.6092	0.4098	0.048*
H32C	0.8714	0.4016	0.4032	0.048*
C41	0.50967 (16)	0.7346 (2)	0.36505 (4)	0.0218 (3)
H41	0.5375	0.8732	0.3659	0.026*
C42	0.55522 (16)	0.6296 (2)	0.33171 (4)	0.0207 (3)
H42	0.5279	0.4908	0.3311	0.025*
C421	0.64460 (15)	0.7119 (2)	0.29577 (4)	0.0203 (3)
C422	0.72004 (17)	0.9002 (2)	0.29629 (4)	0.0245 (3)
H422	0.7169	0.9796	0.3209	0.029*
C423	0.79950 (17)	0.9730 (2)	0.26140 (4)	0.0258 (3)
H423	0.8496	1.1021	0.2621	0.031*
C424	0.80597 (16)	0.8576 (2)	0.22548 (4)	0.0236 (3)
C425	0.73412 (18)	0.6685 (2)	0.22450 (4)	0.0280 (3)
H425	0.7395	0.5887	0.2000	0.034*
C426	0.65429 (17)	0.5967 (2)	0.25951 (4)	0.0255 (3)
H426	0.6054	0.4669	0.2588	0.031*
C427	0.89461 (18)	0.9343 (2)	0.18789 (4)	0.0284 (3)
F471	1.04888 (11)	0.85971 (18)	0.18484 (3)	0.0461 (3)
F472	0.90958 (14)	1.13364 (15)	0.18753 (3)	0.0461 (3)
F473	0.81762 (11)	0.88303 (14)	0.15231 (2)	0.0328 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0276 (6)	0.0200 (6)	0.0190 (5)	−0.0029 (4)	0.0008 (4)	0.0013 (4)
C2	0.0292 (7)	0.0162 (6)	0.0187 (6)	−0.0027 (5)	−0.0015 (5)	0.0002 (5)
C3	0.0263 (6)	0.0155 (6)	0.0177 (6)	−0.0003 (5)	0.0004 (5)	−0.0025 (5)
C4	0.0265 (6)	0.0176 (6)	0.0161 (6)	0.0001 (5)	0.0010 (5)	−0.0021 (5)
C4A	0.0284 (7)	0.0190 (6)	0.0165 (6)	0.0021 (5)	0.0020 (5)	−0.0003 (5)
C5	0.0418 (8)	0.0288 (8)	0.0234 (7)	0.0117 (6)	0.0097 (6)	0.0084 (6)
C6	0.0478 (9)	0.0338 (9)	0.0331 (8)	0.0201 (7)	0.0104 (7)	0.0105 (7)
C7	0.0337 (8)	0.0350 (8)	0.0315 (8)	0.0112 (7)	0.0099 (6)	0.0015 (7)
C8	0.0280 (7)	0.0284 (7)	0.0226 (7)	0.0001 (6)	0.0058 (5)	0.0013 (6)
C8A	0.0253 (6)	0.0202 (6)	0.0166 (6)	−0.0006 (5)	0.0001 (5)	−0.0006 (5)
C21	0.0404 (8)	0.0206 (7)	0.0250 (7)	0.0020 (6)	0.0012 (6)	0.0056 (6)
C31	0.0356 (7)	0.0189 (7)	0.0199 (6)	0.0066 (6)	0.0038 (5)	0.0025 (5)
O31	0.0541 (7)	0.0205 (5)	0.0426 (7)	0.0076 (5)	0.0088 (5)	−0.0074 (5)
C32	0.0281 (7)	0.0367 (8)	0.0311 (8)	0.0088 (6)	0.0020 (6)	0.0001 (7)
C41	0.0267 (6)	0.0177 (6)	0.0210 (6)	0.0024 (5)	0.0029 (5)	0.0013 (5)
C42	0.0225 (6)	0.0198 (6)	0.0200 (6)	−0.0003 (5)	0.0007 (5)	0.0004 (5)
C421	0.0191 (6)	0.0234 (7)	0.0185 (6)	0.0024 (5)	0.0006 (5)	−0.0004 (5)
C422	0.0270 (7)	0.0262 (7)	0.0202 (7)	−0.0020 (5)	0.0031 (5)	−0.0047 (5)
C423	0.0265 (7)	0.0253 (7)	0.0256 (7)	−0.0042 (5)	0.0023 (5)	−0.0005 (6)
C424	0.0215 (6)	0.0302 (7)	0.0193 (6)	−0.0008 (5)	0.0015 (5)	0.0024 (6)
C425	0.0333 (7)	0.0326 (8)	0.0182 (7)	−0.0035 (6)	0.0038 (5)	−0.0052 (6)
C426	0.0293 (7)	0.0250 (7)	0.0224 (7)	−0.0039 (6)	0.0033 (5)	−0.0031 (6)
C427	0.0276 (7)	0.0349 (8)	0.0226 (7)	−0.0008 (6)	0.0027 (5)	0.0038 (6)
F471	0.0250 (4)	0.0760 (8)	0.0377 (5)	0.0060 (5)	0.0088 (4)	0.0219 (5)
F472	0.0679 (7)	0.0365 (5)	0.0341 (5)	−0.0151 (5)	0.0131 (5)	0.0051 (4)
F473	0.0361 (5)	0.0443 (5)	0.0182 (4)	0.0004 (4)	0.0018 (3)	0.0027 (4)

Geometric parameters (Å, º) top

N1—C2	1.3154 (18)	C31—C32	1.495 (2)
N1—C8A	1.3710 (17)	C32—H32A	0.9800
C2—C3	1.4324 (18)	C32—H32B	0.9800
C2—C21	1.5062 (18)	C32—H32C	0.9800
C3—C4	1.3772 (18)	C41—C42	1.3335 (18)
C3—C31	1.5077 (18)	C41—H41	0.9500
C4—C4A	1.4304 (18)	C42—C421	1.4729 (18)
C4—C41	1.4746 (18)	C42—H42	0.9500
C4A—C5	1.4102 (19)	C421—C422	1.3942 (19)
C4A—C8A	1.4175 (18)	C421—C426	1.3969 (19)
C5—C6	1.367 (2)	C422—C423	1.3843 (19)
C5—H5	0.9500	C422—H422	0.9500
C6—C7	1.407 (2)	C423—C424	1.387 (2)
C6—H6	0.9500	C423—H423	0.9500
C7—C8	1.365 (2)	C424—C425	1.386 (2)
C7—H7	0.9500	C424—C427	1.4991 (19)
C8—C8A	1.4151 (19)	C425—C426	1.3866 (19)
C8—H8	0.9500	C425—H425	0.9500
C21—H21A	0.9800	C426—H426	0.9500
C21—H21B	0.9800	C427—F472	1.3326 (18)
C21—H21C	0.9800	C427—F473	1.3392 (17)
C31—O31	1.2105 (18)	C427—F471	1.3465 (17)

C2—N1—C8A	118.41 (11)	C31—C32—H32A	109.5
N1—C2—C3	122.93 (12)	C31—C32—H32B	109.5
N1—C2—C21	116.62 (12)	H32A—C32—H32B	109.5
C3—C2—C21	120.42 (12)	C31—C32—H32C	109.5
C4—C3—C2	119.77 (12)	H32A—C32—H32C	109.5
C4—C3—C31	120.76 (12)	H32B—C32—H32C	109.5
C2—C3—C31	119.39 (12)	C42—C41—C4	124.41 (12)
C3—C4—C4A	118.13 (12)	C42—C41—H41	117.8
C3—C4—C41	122.77 (12)	C4—C41—H41	117.8
C4A—C4—C41	119.10 (12)	C41—C42—C421	125.11 (13)
C5—C4A—C8A	118.78 (12)	C41—C42—H42	117.4
C5—C4A—C4	123.17 (12)	C421—C42—H42	117.4
C8A—C4A—C4	118.04 (12)	C422—C421—C426	118.39 (12)
C6—C5—C4A	120.67 (14)	C422—C421—C42	122.90 (12)
C6—C5—H5	119.7	C426—C421—C42	118.72 (12)
C4A—C5—H5	119.7	C423—C422—C421	120.76 (13)
C5—C6—C7	120.36 (14)	C423—C422—H422	119.6
C5—C6—H6	119.8	C421—C422—H422	119.6
C7—C6—H6	119.8	C422—C423—C424	120.03 (13)
C8—C7—C6	120.60 (14)	C422—C423—H423	120.0
C8—C7—H7	119.7	C424—C423—H423	120.0
C6—C7—H7	119.7	C425—C424—C423	120.15 (13)
C7—C8—C8A	120.11 (13)	C425—C424—C427	119.64 (13)
C7—C8—H8	119.9	C423—C424—C427	120.19 (13)
C8A—C8—H8	119.9	C424—C425—C426	119.55 (13)
N1—C8A—C8	117.86 (12)	C424—C425—H425	120.2
N1—C8A—C4A	122.69 (12)	C426—C425—H425	120.2
C8—C8A—C4A	119.44 (12)	C425—C426—C421	121.10 (13)
C2—C21—H21A	109.5	C425—C426—H426	119.5
C2—C21—H21B	109.5	C421—C426—H426	119.5
H21A—C21—H21B	109.5	F472—C427—F473	106.72 (12)
C2—C21—H21C	109.5	F472—C427—F471	106.39 (13)
H21A—C21—H21C	109.5	F473—C427—F471	105.47 (12)
H21B—C21—H21C	109.5	F472—C427—C424	112.97 (13)
O31—C31—C32	122.68 (14)	F473—C427—C424	112.21 (12)
O31—C31—C3	121.26 (14)	F471—C427—C424	112.54 (12)
C32—C31—C3	115.94 (12)

C8A—N1—C2—C3	1.51 (19)	C4—C4A—C8A—C8	179.55 (12)
C8A—N1—C2—C21	179.47 (12)	C4—C3—C31—O31	−113.91 (16)
N1—C2—C3—C4	−0.5 (2)	C2—C3—C31—O31	69.52 (18)
C21—C2—C3—C4	−178.38 (12)	C4—C3—C31—C32	69.90 (17)
N1—C2—C3—C31	176.10 (12)	C2—C3—C31—C32	−106.67 (15)
C21—C2—C3—C31	−1.78 (19)	C3—C4—C41—C42	49.0 (2)
C2—C3—C4—C4A	−1.18 (19)	C4A—C4—C41—C42	−130.33 (14)
C31—C3—C4—C4A	−177.74 (12)	C4—C41—C42—C421	179.51 (12)
C2—C3—C4—C41	179.44 (12)	C41—C42—C421—C422	13.0 (2)
C31—C3—C4—C41	2.9 (2)	C41—C42—C421—C426	−166.89 (13)
C3—C4—C4A—C5	−176.83 (13)	C426—C421—C422—C423	1.4 (2)
C41—C4—C4A—C5	2.6 (2)	C42—C421—C422—C423	−178.54 (13)
C3—C4—C4A—C8A	1.77 (19)	C421—C422—C423—C424	−0.5 (2)
C41—C4—C4A—C8A	−178.83 (12)	C422—C423—C424—C425	−0.5 (2)
C8A—C4A—C5—C6	0.1 (2)	C422—C423—C424—C427	−178.86 (13)
C4—C4A—C5—C6	178.67 (15)	C423—C424—C425—C426	0.7 (2)
C4A—C5—C6—C7	1.4 (3)	C427—C424—C425—C426	179.06 (13)
C5—C6—C7—C8	−1.1 (3)	C424—C425—C426—C421	0.2 (2)
C6—C7—C8—C8A	−0.6 (2)	C422—C421—C426—C425	−1.2 (2)
C2—N1—C8A—C8	178.81 (12)	C42—C421—C426—C425	178.73 (13)
C2—N1—C8A—C4A	−0.84 (19)	C425—C424—C427—F472	159.37 (13)
C7—C8—C8A—N1	−177.60 (14)	C423—C424—C427—F472	−22.27 (19)
C7—C8—C8A—C4A	2.1 (2)	C425—C424—C427—F473	38.67 (19)
C5—C4A—C8A—N1	177.86 (13)	C423—C424—C427—F473	−142.98 (13)
C4—C4A—C8A—N1	−0.8 (2)	C425—C424—C427—F471	−80.11 (17)
C5—C4A—C8A—C8	−1.8 (2)	C423—C424—C427—F471	98.24 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C41—H41···O31ⁱ	0.95	2.42	3.3290 (17)	161
C426—H426···Cg3ⁱⁱ	0.95	3.00	3.7621 (15)	138

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

Ethyl (E)-4-[2-(4-methoxyphenyl)ethenyl]-2-methylquinoline-3-carboxylate (IV) top

Crystal data top

C₂₂H₂₁NO₃	Z = 2
M_r = 347.40	F(000) = 368
Triclinic, P1	D_x = 1.279 Mg m⁻³
a = 9.5301 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.3513 (8) Å	Cell parameters from 4158 reflections
c = 10.3621 (8) Å	θ = 2.2–27.5°
α = 65.374 (3)°	µ = 0.09 mm⁻¹
β = 86.583 (3)°	T = 100 K
γ = 76.376 (3)°	Needle, yellow
V = 902.23 (13) Å³	0.30 × 0.12 × 0.05 mm

Data collection top

Bruker D8 Venture diffractometer	4158 independent reflections
Radiation source: INCOATEC high brilliance microfocus sealed tube	3440 reflections with I > 2σ(I)
Multilayer mirror monochromator	R_int = 0.053
φ and ω scans	θ_max = 27.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2016)	h = −12→12
T_min = 0.954, T_max = 0.996	k = −13→13
44489 measured reflections	l = −13→13

Refinement top

Refinement on F²	Primary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.052	H-atom parameters constrained
wR(F²) = 0.128	w = 1/[σ²(F_o²) + (0.0422P)² + 0.7299P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
4158 reflections	Δρ_max = 0.36 e Å⁻³
238 parameters	Δρ_min = −0.21 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	0.81102 (16)	0.42663 (16)	0.95018 (15)	0.0239 (3)
C2	0.81545 (18)	0.31117 (19)	0.92506 (17)	0.0228 (3)
C3	0.70247 (18)	0.30251 (18)	0.84572 (17)	0.0206 (3)
C4	0.58290 (17)	0.41582 (18)	0.79378 (16)	0.0199 (3)
C4A	0.57445 (18)	0.53964 (18)	0.82549 (16)	0.0204 (3)
C5	0.45312 (19)	0.65895 (18)	0.78548 (17)	0.0242 (4)
H5	0.3727	0.6588	0.7356	0.029*
C6	0.4503 (2)	0.77485 (19)	0.81796 (19)	0.0291 (4)
H6	0.3683	0.8548	0.7901	0.035*
C7	0.5683 (2)	0.7762 (2)	0.89237 (18)	0.0294 (4)
H7	0.5659	0.8576	0.9136	0.035*
C8	0.6858 (2)	0.6619 (2)	0.93411 (18)	0.0272 (4)
H8	0.7647	0.6639	0.9846	0.033*
C8A	0.69172 (18)	0.53980 (19)	0.90306 (16)	0.0221 (3)
C21	0.94750 (19)	0.1883 (2)	0.9796 (2)	0.0312 (4)
H21A	0.9206	0.1020	1.0531	0.047*
H21B	1.0182	0.2176	1.0202	0.047*
H21C	0.9899	0.1649	0.9012	0.047*
C31	0.72030 (17)	0.16500 (19)	0.82311 (18)	0.0221 (3)
O31	0.70662 (14)	0.05033 (13)	0.91571 (13)	0.0296 (3)
O32	0.75597 (14)	0.18596 (14)	0.69062 (13)	0.0286 (3)
C32	0.7718 (2)	0.0610 (2)	0.6539 (2)	0.0325 (4)
H32A	0.8004	−0.0312	0.7402	0.039*
H32B	0.8486	0.0633	0.5848	0.039*
C33	0.6316 (2)	0.0661 (2)	0.59060 (19)	0.0317 (4)
H33A	0.6002	0.1602	0.5089	0.048*
H33B	0.5579	0.0548	0.6621	0.048*
H33C	0.6453	−0.0132	0.5595	0.048*
C41	0.46640 (17)	0.41644 (18)	0.70556 (17)	0.0204 (3)
H41	0.4353	0.5012	0.6202	0.024*
C42	0.40176 (17)	0.30632 (18)	0.73726 (17)	0.0203 (3)
H42	0.4315	0.2241	0.8249	0.024*
C421	0.28969 (17)	0.29870 (18)	0.65120 (16)	0.0193 (3)
C422	0.23677 (18)	0.40931 (19)	0.51900 (17)	0.0230 (3)
H422	0.2688	0.4976	0.4846	0.028*
C423	0.13813 (18)	0.3931 (2)	0.43659 (18)	0.0251 (4)
H423	0.1030	0.4698	0.3469	0.030*
C424	0.09112 (18)	0.2639 (2)	0.48622 (18)	0.0242 (4)
C425	0.13894 (19)	0.1541 (2)	0.61989 (19)	0.0269 (4)
H425	0.1046	0.0671	0.6552	0.032*
C426	0.23657 (18)	0.17209 (18)	0.70116 (18)	0.0232 (3)
H426	0.2681	0.0970	0.7926	0.028*
O424	−0.00165 (14)	0.23441 (16)	0.41192 (13)	0.0334 (3)
C427	−0.0515 (2)	0.3436 (2)	0.2731 (2)	0.0355 (5)
H47A	0.0316	0.3680	0.2155	0.053*
H47B	−0.1105	0.4313	0.2807	0.053*
H47C	−0.1098	0.3061	0.2280	0.053*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0264 (7)	0.0304 (8)	0.0188 (7)	−0.0121 (6)	−0.0007 (5)	−0.0107 (6)
C2	0.0238 (8)	0.0285 (9)	0.0175 (8)	−0.0093 (7)	−0.0003 (6)	−0.0090 (7)
C3	0.0237 (8)	0.0236 (8)	0.0176 (7)	−0.0087 (6)	0.0008 (6)	−0.0097 (6)
C4	0.0241 (8)	0.0232 (8)	0.0143 (7)	−0.0107 (6)	0.0011 (6)	−0.0070 (6)
C4A	0.0260 (8)	0.0222 (8)	0.0147 (7)	−0.0110 (6)	0.0035 (6)	−0.0068 (6)
C5	0.0306 (9)	0.0222 (8)	0.0178 (8)	−0.0088 (7)	0.0010 (6)	−0.0050 (6)
C6	0.0412 (10)	0.0209 (9)	0.0224 (8)	−0.0072 (7)	0.0024 (7)	−0.0064 (7)
C7	0.0494 (11)	0.0226 (9)	0.0206 (8)	−0.0154 (8)	0.0057 (7)	−0.0100 (7)
C8	0.0395 (10)	0.0307 (9)	0.0177 (8)	−0.0193 (8)	0.0031 (7)	−0.0106 (7)
C8A	0.0289 (9)	0.0263 (8)	0.0142 (7)	−0.0132 (7)	0.0036 (6)	−0.0082 (6)
C21	0.0248 (9)	0.0369 (10)	0.0346 (10)	−0.0043 (8)	−0.0078 (7)	−0.0179 (8)
C31	0.0176 (7)	0.0263 (9)	0.0246 (8)	−0.0047 (6)	−0.0033 (6)	−0.0125 (7)
O31	0.0380 (7)	0.0229 (6)	0.0270 (7)	−0.0067 (5)	−0.0055 (5)	−0.0087 (5)
O32	0.0323 (7)	0.0346 (7)	0.0294 (7)	−0.0138 (6)	0.0065 (5)	−0.0208 (6)
C32	0.0321 (10)	0.0394 (11)	0.0409 (11)	−0.0128 (8)	0.0086 (8)	−0.0297 (9)
C33	0.0440 (11)	0.0314 (10)	0.0246 (9)	−0.0154 (8)	−0.0012 (8)	−0.0126 (8)
C41	0.0221 (8)	0.0227 (8)	0.0161 (7)	−0.0040 (6)	−0.0029 (6)	−0.0079 (6)
C42	0.0205 (8)	0.0231 (8)	0.0168 (7)	−0.0031 (6)	−0.0021 (6)	−0.0086 (6)
C421	0.0187 (7)	0.0231 (8)	0.0180 (7)	−0.0043 (6)	−0.0005 (6)	−0.0104 (6)
C422	0.0250 (8)	0.0256 (9)	0.0188 (8)	−0.0090 (7)	−0.0002 (6)	−0.0078 (7)
C423	0.0235 (8)	0.0317 (9)	0.0180 (8)	−0.0059 (7)	−0.0025 (6)	−0.0082 (7)
C424	0.0186 (8)	0.0366 (10)	0.0221 (8)	−0.0085 (7)	−0.0007 (6)	−0.0155 (7)
C425	0.0264 (9)	0.0286 (9)	0.0276 (9)	−0.0117 (7)	−0.0020 (7)	−0.0103 (7)
C426	0.0235 (8)	0.0234 (8)	0.0204 (8)	−0.0055 (7)	−0.0033 (6)	−0.0064 (7)
O424	0.0319 (7)	0.0486 (8)	0.0252 (7)	−0.0185 (6)	−0.0057 (5)	−0.0150 (6)
C427	0.0259 (9)	0.0599 (13)	0.0257 (9)	−0.0122 (9)	−0.0055 (7)	−0.0205 (9)

Geometric parameters (Å, º) top

N1—C2	1.316 (2)	C32—H32A	0.9900
N1—C8A	1.366 (2)	C32—H32B	0.9900
C2—C3	1.434 (2)	C33—H33A	0.9800
C2—C21	1.501 (2)	C33—H33B	0.9800
C3—C4	1.372 (2)	C33—H33C	0.9800
C3—C31	1.506 (2)	C41—C42	1.335 (2)
C4—C4A	1.434 (2)	C41—H41	0.9500
C4—C41	1.477 (2)	C42—C421	1.468 (2)
C4A—C5	1.411 (2)	C42—H42	0.9500
C4A—C8A	1.416 (2)	C421—C422	1.395 (2)
C5—C6	1.369 (2)	C421—C426	1.399 (2)
C5—H5	0.9500	C422—C423	1.389 (2)
C6—C7	1.407 (3)	C422—H422	0.9500
C6—H6	0.9500	C423—C424	1.391 (2)
C7—C8	1.359 (3)	C423—H423	0.9500
C7—H7	0.9500	C424—O424	1.3682 (19)
C8—C8A	1.417 (2)	C424—C425	1.392 (2)
C8—H8	0.9500	C425—C426	1.384 (2)
C21—H21A	0.9800	C425—H425	0.9500
C21—H21B	0.9800	C426—H426	0.9500
C21—H21C	0.9800	O424—C427	1.430 (2)
C31—O31	1.206 (2)	C427—H47A	0.9800
C31—O32	1.334 (2)	C427—H47B	0.9800
O32—C32	1.467 (2)	C427—H47C	0.9800
C32—C33	1.503 (3)

C2—N1—C8A	118.47 (14)	O32—C32—H32B	109.6
N1—C2—C3	122.42 (16)	C33—C32—H32B	109.6
N1—C2—C21	117.03 (15)	H32A—C32—H32B	108.2
C3—C2—C21	120.52 (15)	C32—C33—H33A	109.5
C4—C3—C2	120.55 (15)	C32—C33—H33B	109.5
C4—C3—C31	121.94 (14)	H33A—C33—H33B	109.5
C2—C3—C31	117.51 (15)	C32—C33—H33C	109.5
C3—C4—C4A	117.41 (14)	H33A—C33—H33C	109.5
C3—C4—C41	123.09 (14)	H33B—C33—H33C	109.5
C4A—C4—C41	119.49 (15)	C42—C41—C4	124.64 (15)
C5—C4A—C8A	118.99 (15)	C42—C41—H41	117.7
C5—C4A—C4	122.73 (15)	C4—C41—H41	117.7
C8A—C4A—C4	118.26 (15)	C41—C42—C421	126.96 (15)
C6—C5—C4A	120.54 (16)	C41—C42—H42	116.5
C6—C5—H5	119.7	C421—C42—H42	116.5
C4A—C5—H5	119.7	C422—C421—C426	117.94 (14)
C5—C6—C7	120.35 (17)	C422—C421—C42	123.34 (15)
C5—C6—H6	119.8	C426—C421—C42	118.68 (14)
C7—C6—H6	119.8	C423—C422—C421	121.39 (16)
C8—C7—C6	120.45 (16)	C423—C422—H422	119.3
C8—C7—H7	119.8	C421—C422—H422	119.3
C6—C7—H7	119.8	C422—C423—C424	119.57 (16)
C7—C8—C8A	120.61 (16)	C422—C423—H423	120.2
C7—C8—H8	119.7	C424—C423—H423	120.2
C8A—C8—H8	119.7	O424—C424—C423	124.44 (16)
N1—C8A—C4A	122.83 (15)	O424—C424—C425	115.64 (16)
N1—C8A—C8	118.15 (15)	C423—C424—C425	119.92 (15)
C4A—C8A—C8	119.02 (16)	C426—C425—C424	119.84 (16)
C2—C21—H21A	109.5	C426—C425—H425	120.1
C2—C21—H21B	109.5	C424—C425—H425	120.1
H21A—C21—H21B	109.5	C425—C426—C421	121.25 (16)
C2—C21—H21C	109.5	C425—C426—H426	119.4
H21A—C21—H21C	109.5	C421—C426—H426	119.4
H21B—C21—H21C	109.5	C424—O424—C427	117.37 (15)
O31—C31—O32	125.09 (15)	O424—C427—H47A	109.5
O31—C31—C3	123.28 (15)	O424—C427—H47B	109.5
O32—C31—C3	111.61 (14)	H47A—C427—H47B	109.5
C31—O32—C32	116.83 (14)	O424—C427—H47C	109.5
O32—C32—C33	110.10 (15)	H47A—C427—H47C	109.5
O32—C32—H32A	109.6	H47B—C427—H47C	109.5
C33—C32—H32A	109.6

C8A—N1—C2—C3	2.4 (2)	C7—C8—C8A—C4A	1.2 (2)
C8A—N1—C2—C21	−179.40 (15)	C4—C3—C31—O31	−106.0 (2)
N1—C2—C3—C4	−0.8 (3)	C2—C3—C31—O31	73.7 (2)
C21—C2—C3—C4	−178.89 (16)	C4—C3—C31—O32	75.5 (2)
N1—C2—C3—C31	179.59 (15)	C2—C3—C31—O32	−104.85 (17)
C21—C2—C3—C31	1.5 (2)	O31—C31—O32—C32	3.5 (2)
C2—C3—C4—C4A	−1.7 (2)	C3—C31—O32—C32	−178.03 (14)
C31—C3—C4—C4A	177.92 (14)	C31—O32—C32—C33	93.04 (19)
C2—C3—C4—C41	176.96 (15)	C3—C4—C41—C42	48.8 (2)
C31—C3—C4—C41	−3.4 (2)	C4A—C4—C41—C42	−132.53 (17)
C3—C4—C4A—C5	−176.06 (15)	C4—C41—C42—C421	−177.48 (15)
C41—C4—C4A—C5	5.2 (2)	C41—C42—C421—C422	1.2 (3)
C3—C4—C4A—C8A	2.4 (2)	C41—C42—C421—C426	178.77 (16)
C41—C4—C4A—C8A	−176.28 (14)	C426—C421—C422—C423	−2.2 (2)
C8A—C4A—C5—C6	1.7 (2)	C42—C421—C422—C423	175.34 (15)
C4—C4A—C5—C6	−179.86 (16)	C421—C422—C423—C424	−0.2 (3)
C4A—C5—C6—C7	−0.3 (3)	C422—C423—C424—O424	−177.63 (16)
C5—C6—C7—C8	−0.7 (3)	C422—C423—C424—C425	2.3 (3)
C6—C7—C8—C8A	0.2 (3)	O424—C424—C425—C426	177.99 (16)
C2—N1—C8A—C4A	−1.6 (2)	C423—C424—C425—C426	−2.0 (3)
C2—N1—C8A—C8	178.18 (15)	C424—C425—C426—C421	−0.5 (3)
C5—C4A—C8A—N1	177.69 (15)	C422—C421—C426—C425	2.6 (2)
C4—C4A—C8A—N1	−0.9 (2)	C42—C421—C426—C425	−175.09 (15)
C5—C4A—C8A—C8	−2.1 (2)	C423—C424—O424—C427	0.9 (3)
C4—C4A—C8A—C8	179.38 (15)	C425—C424—O424—C427	−179.02 (16)
C7—C8—C8A—N1	−178.61 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C32—H32B···O424ⁱ	0.99	2.57	3.406 (2)	142
C423—H423···Cg1ⁱⁱ	0.95	2.91	3.4894 (19)	120

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

Ethyl (E)-4-[2-(4-bromophenyl)ethenyl]-2-methylquinoline-3-carboxylate (V) top

Crystal data top

C₂₁H₁₈BrNO₂	F(000) = 808
M_r = 396.26	D_x = 1.424 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.5709 (6) Å	Cell parameters from 4558 reflections
b = 10.6119 (7) Å	θ = 2.2–28.3°
c = 18.2074 (10) Å	µ = 2.24 mm⁻¹
β = 90.939 (2)°	T = 100 K
V = 1849.0 (2) Å³	Block, yellow
Z = 4	0.25 × 0.18 × 0.15 mm

Data collection top

Bruker D8 Venture diffractometer	4588 independent reflections
Radiation source: INCOATEC high brilliance microfocus sealed tube	4098 reflections with I > 2σ(I)
Multilayer mirror monochromator	R_int = 0.041
φ and ω scans	θ_max = 28.3°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2016)	h = −12→12
T_min = 0.595, T_max = 0.715	k = −14→14
54534 measured reflections	l = −24→24

Refinement top

Refinement on F²	Primary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.022	H-atom parameters constrained
wR(F²) = 0.056	w = 1/[σ²(F_o²) + (0.0237P)² + 1.0895P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.003
4588 reflections	Δρ_max = 0.35 e Å⁻³
228 parameters	Δρ_min = −0.42 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	0.22794 (12)	0.20653 (11)	0.63602 (6)	0.0186 (2)
C2	0.36010 (14)	0.19499 (13)	0.61835 (7)	0.0179 (3)
C3	0.45699 (14)	0.29687 (13)	0.62494 (7)	0.0161 (2)
C4	0.41542 (14)	0.41110 (12)	0.65325 (7)	0.0156 (2)
C4A	0.27233 (14)	0.42464 (13)	0.67343 (7)	0.0165 (3)
C5	0.21593 (15)	0.53906 (14)	0.70002 (8)	0.0211 (3)
H5	0.2756	0.6092	0.7086	0.025*
C6	0.07589 (16)	0.54916 (15)	0.71338 (8)	0.0249 (3)
H6	0.0390	0.6264	0.7309	0.030*
C7	−0.01353 (16)	0.44582 (15)	0.70130 (9)	0.0261 (3)
H7	−0.1106	0.4540	0.7104	0.031*
C8	0.03799 (15)	0.33360 (14)	0.67658 (8)	0.0225 (3)
H8	−0.0232	0.2641	0.6692	0.027*
C8A	0.18202 (14)	0.32044 (13)	0.66196 (7)	0.0172 (3)
C21	0.40674 (16)	0.06875 (14)	0.59035 (9)	0.0269 (3)
H21A	0.3382	0.0044	0.6036	0.040*
H21B	0.4978	0.0475	0.6124	0.040*
H21C	0.4146	0.0721	0.5368	0.040*
C31	0.60558 (14)	0.27447 (13)	0.60265 (7)	0.0181 (3)
O31	0.70170 (11)	0.25715 (11)	0.64455 (6)	0.0248 (2)
O32	0.61517 (11)	0.27338 (11)	0.52926 (5)	0.0241 (2)
C32	0.75437 (17)	0.25167 (17)	0.49963 (9)	0.0306 (3)
H32A	0.7455	0.2142	0.4500	0.037*
H32B	0.8060	0.1914	0.5315	0.037*
C33	0.83439 (18)	0.37338 (18)	0.49542 (9)	0.0339 (4)
H33A	0.7802	0.4348	0.4666	0.051*
H33B	0.9241	0.3584	0.4718	0.051*
H33C	0.8510	0.4062	0.5451	0.051*
C41	0.51187 (14)	0.51853 (12)	0.66208 (7)	0.0168 (3)
H41	0.5177	0.5591	0.7086	0.020*
C42	0.59134 (15)	0.56169 (13)	0.60807 (7)	0.0185 (3)
H42	0.5825	0.5209	0.5618	0.022*
C421	0.69122 (14)	0.66634 (13)	0.61359 (7)	0.0174 (3)
C422	0.73110 (15)	0.72094 (13)	0.68058 (7)	0.0189 (3)
H422	0.6918	0.6908	0.7248	0.023*
C423	0.82710 (14)	0.81836 (13)	0.68316 (7)	0.0188 (3)
H423	0.8536	0.8552	0.7289	0.023*
C424	0.88435 (14)	0.86183 (12)	0.61828 (7)	0.0176 (3)
Br42	1.02007 (2)	0.99228 (2)	0.62329 (2)	0.02109 (5)
C425	0.84705 (16)	0.81022 (14)	0.55109 (8)	0.0235 (3)
H425	0.8861	0.8412	0.5070	0.028*
C426	0.75115 (16)	0.71199 (14)	0.54958 (8)	0.0235 (3)
H426	0.7257	0.6750	0.5038	0.028*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0177 (6)	0.0175 (5)	0.0206 (6)	−0.0064 (4)	0.0008 (4)	0.0001 (4)
C2	0.0191 (7)	0.0169 (6)	0.0178 (6)	−0.0046 (5)	0.0003 (5)	−0.0006 (5)
C3	0.0147 (6)	0.0187 (6)	0.0149 (6)	−0.0045 (5)	0.0009 (5)	0.0007 (5)
C4	0.0158 (6)	0.0170 (6)	0.0138 (6)	−0.0049 (5)	−0.0018 (5)	0.0018 (5)
C4A	0.0160 (6)	0.0180 (6)	0.0156 (6)	−0.0034 (5)	−0.0003 (5)	0.0008 (5)
C5	0.0200 (7)	0.0199 (6)	0.0233 (7)	−0.0036 (5)	−0.0003 (5)	−0.0028 (5)
C6	0.0212 (7)	0.0262 (7)	0.0274 (7)	0.0023 (6)	−0.0001 (6)	−0.0064 (6)
C7	0.0161 (7)	0.0326 (8)	0.0295 (8)	−0.0016 (6)	0.0020 (6)	−0.0028 (6)
C8	0.0159 (7)	0.0265 (7)	0.0251 (7)	−0.0070 (5)	0.0008 (5)	−0.0011 (6)
C8A	0.0155 (6)	0.0195 (6)	0.0167 (6)	−0.0045 (5)	0.0007 (5)	0.0012 (5)
C21	0.0246 (8)	0.0188 (7)	0.0374 (8)	−0.0057 (6)	0.0054 (6)	−0.0077 (6)
C31	0.0179 (6)	0.0169 (6)	0.0194 (6)	−0.0048 (5)	0.0019 (5)	−0.0020 (5)
O31	0.0167 (5)	0.0347 (6)	0.0231 (5)	−0.0001 (4)	−0.0004 (4)	0.0009 (4)
O32	0.0202 (5)	0.0344 (6)	0.0178 (5)	−0.0032 (4)	0.0034 (4)	−0.0043 (4)
C32	0.0250 (8)	0.0413 (9)	0.0258 (8)	−0.0002 (7)	0.0109 (6)	−0.0066 (7)
C33	0.0262 (8)	0.0466 (10)	0.0293 (8)	−0.0023 (7)	0.0084 (7)	0.0050 (7)
C41	0.0153 (6)	0.0167 (6)	0.0184 (6)	−0.0038 (5)	−0.0019 (5)	−0.0004 (5)
C42	0.0202 (7)	0.0185 (6)	0.0165 (6)	−0.0070 (5)	−0.0027 (5)	−0.0003 (5)
C421	0.0171 (6)	0.0174 (6)	0.0175 (6)	−0.0054 (5)	−0.0013 (5)	0.0010 (5)
C422	0.0201 (7)	0.0206 (6)	0.0162 (6)	−0.0066 (5)	0.0028 (5)	−0.0002 (5)
C423	0.0191 (7)	0.0194 (6)	0.0179 (6)	−0.0068 (5)	0.0011 (5)	−0.0029 (5)
C424	0.0160 (6)	0.0158 (6)	0.0211 (6)	−0.0069 (5)	0.0003 (5)	0.0003 (5)
Br42	0.02136 (8)	0.02079 (8)	0.02118 (7)	−0.01179 (5)	0.00231 (5)	−0.00103 (5)
C425	0.0268 (8)	0.0264 (7)	0.0174 (6)	−0.0125 (6)	0.0020 (6)	0.0032 (5)
C426	0.0286 (8)	0.0261 (7)	0.0158 (6)	−0.0132 (6)	−0.0015 (5)	−0.0004 (5)

Geometric parameters (Å, º) top

N1—C2	1.3160 (18)	O32—C32	1.4638 (17)
N1—C8A	1.3725 (18)	C32—C33	1.504 (2)
C2—C3	1.4282 (18)	C32—H32A	0.9900
C2—C21	1.5038 (19)	C32—H32B	0.9900
C3—C4	1.3784 (19)	C33—H33A	0.9800
C3—C31	1.5042 (19)	C33—H33B	0.9800
C4—C4A	1.4309 (18)	C33—H33C	0.9800
C4—C41	1.4741 (18)	C41—C42	1.3341 (19)
C4A—C8A	1.4168 (18)	C41—H41	0.9500
C4A—C5	1.4173 (19)	C42—C421	1.4676 (18)
C5—C6	1.370 (2)	C42—H42	0.9500
C5—H5	0.9500	C421—C426	1.3942 (19)
C6—C7	1.406 (2)	C421—C422	1.3977 (18)
C6—H6	0.9500	C422—C423	1.3834 (18)
C7—C8	1.368 (2)	C422—H422	0.9500
C7—H7	0.9500	C423—C424	1.3891 (18)
C8—C8A	1.4152 (19)	C423—H423	0.9500
C8—H8	0.9500	C424—C425	1.3820 (19)
C21—H21A	0.9800	C424—Br42	1.8996 (13)
C21—H21B	0.9800	C425—C426	1.3889 (19)
C21—H21C	0.9800	C425—H425	0.9500
C31—O31	1.1997 (17)	C426—H426	0.9500
C31—O32	1.3409 (17)

C2—N1—C8A	118.72 (12)	C31—O32—C32	116.51 (12)
N1—C2—C3	122.30 (13)	O32—C32—C33	110.54 (13)
N1—C2—C21	117.24 (12)	O32—C32—H32A	109.5
C3—C2—C21	120.46 (12)	C33—C32—H32A	109.5
C4—C3—C2	120.41 (12)	O32—C32—H32B	109.5
C4—C3—C31	121.32 (12)	C33—C32—H32B	109.5
C2—C3—C31	118.24 (12)	H32A—C32—H32B	108.1
C3—C4—C4A	117.88 (12)	C32—C33—H33A	109.5
C3—C4—C41	122.47 (12)	C32—C33—H33B	109.5
C4A—C4—C41	119.64 (12)	H33A—C33—H33B	109.5
C8A—C4A—C5	118.96 (12)	C32—C33—H33C	109.5
C8A—C4A—C4	117.89 (12)	H33A—C33—H33C	109.5
C5—C4A—C4	123.04 (12)	H33B—C33—H33C	109.5
C6—C5—C4A	120.45 (13)	C42—C41—C4	123.28 (12)
C6—C5—H5	119.8	C42—C41—H41	118.4
C4A—C5—H5	119.8	C4—C41—H41	118.4
C5—C6—C7	120.38 (14)	C41—C42—C421	126.00 (13)
C5—C6—H6	119.8	C41—C42—H42	117.0
C7—C6—H6	119.8	C421—C42—H42	117.0
C8—C7—C6	120.58 (14)	C426—C421—C422	118.37 (12)
C8—C7—H7	119.7	C426—C421—C42	118.82 (12)
C6—C7—H7	119.7	C422—C421—C42	122.80 (12)
C7—C8—C8A	120.35 (13)	C423—C422—C421	120.74 (12)
C7—C8—H8	119.8	C423—C422—H422	119.6
C8A—C8—H8	119.8	C421—C422—H422	119.6
N1—C8A—C8	118.03 (12)	C422—C423—C424	119.36 (12)
N1—C8A—C4A	122.69 (12)	C422—C423—H423	120.3
C8—C8A—C4A	119.27 (13)	C424—C423—H423	120.3
C2—C21—H21A	109.5	C425—C424—C423	121.43 (12)
C2—C21—H21B	109.5	C425—C424—Br42	119.86 (10)
H21A—C21—H21B	109.5	C423—C424—Br42	118.69 (10)
C2—C21—H21C	109.5	C424—C425—C426	118.42 (13)
H21A—C21—H21C	109.5	C424—C425—H425	120.8
H21B—C21—H21C	109.5	C426—C425—H425	120.8
O31—C31—O32	124.62 (13)	C425—C426—C421	121.67 (13)
O31—C31—C3	124.83 (12)	C425—C426—H426	119.2
O32—C31—C3	110.53 (12)	C421—C426—H426	119.2

C8A—N1—C2—C3	−0.3 (2)	C5—C4A—C8A—C8	0.6 (2)
C8A—N1—C2—C21	179.82 (13)	C4—C4A—C8A—C8	−175.68 (12)
N1—C2—C3—C4	2.6 (2)	C4—C3—C31—O31	75.39 (19)
C21—C2—C3—C4	−177.51 (13)	C2—C3—C31—O31	−102.56 (17)
N1—C2—C3—C31	−179.45 (12)	C4—C3—C31—O32	−106.17 (14)
C21—C2—C3—C31	0.46 (19)	C2—C3—C31—O32	75.88 (15)
C2—C3—C4—C4A	−1.82 (19)	O31—C31—O32—C32	−1.2 (2)
C31—C3—C4—C4A	−179.73 (12)	C3—C31—O32—C32	−179.65 (12)
C2—C3—C4—C41	179.17 (12)	C31—O32—C32—C33	−85.21 (17)
C31—C3—C4—C41	1.3 (2)	C3—C4—C41—C42	51.4 (2)
C3—C4—C4A—C8A	−0.97 (18)	C4A—C4—C41—C42	−127.57 (15)
C41—C4—C4A—C8A	178.07 (12)	C4—C41—C42—C421	−178.74 (13)
C3—C4—C4A—C5	−177.12 (13)	C41—C42—C421—C426	−170.67 (15)
C41—C4—C4A—C5	1.9 (2)	C41—C42—C421—C422	10.6 (2)
C8A—C4A—C5—C6	−0.9 (2)	C426—C421—C422—C423	0.4 (2)
C4—C4A—C5—C6	175.18 (13)	C42—C421—C422—C423	179.12 (13)
C4A—C5—C6—C7	0.4 (2)	C421—C422—C423—C424	−0.1 (2)
C5—C6—C7—C8	0.5 (2)	C422—C423—C424—C425	0.3 (2)
C6—C7—C8—C8A	−0.8 (2)	C422—C423—C424—Br42	−178.17 (11)
C2—N1—C8A—C8	176.31 (13)	C423—C424—C425—C426	−0.7 (2)
C2—N1—C8A—C4A	−2.7 (2)	Br42—C424—C425—C426	177.77 (12)
C7—C8—C8A—N1	−178.88 (14)	C424—C425—C426—C421	0.9 (2)
C7—C8—C8A—C4A	0.2 (2)	C422—C421—C426—C425	−0.8 (2)
C5—C4A—C8A—N1	179.67 (13)	C42—C421—C426—C425	−179.57 (14)
C4—C4A—C8A—N1	3.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C423—H423···O31ⁱ	0.95	2.59	3.2197 (17)	124
C426—H426···Cg1ⁱⁱ	0.95	2.74	3.5961 (16)	151

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

Ethyl (E)-2-methyl-4-{2-[4-(trifluoromethyl)phenyl]ethenyl}quinoline-3-carboxylate (VI) top

Crystal data top

C₂₂H₁₈F₃NO₂	Z = 2
M_r = 385.37	F(000) = 400
Triclinic, P1	D_x = 1.417 Mg m⁻³
a = 8.7465 (10) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.9436 (11) Å	Cell parameters from 4022 reflections
c = 11.1116 (11) Å	θ = 2.2–28.3°
α = 105.446 (4)°	µ = 0.11 mm⁻¹
β = 99.763 (4)°	T = 100 K
γ = 97.204 (4)°	Block, yellow
V = 903.08 (17) Å³	0.27 × 0.20 × 0.18 mm

Data collection top

Bruker D8 Venture diffractometer	4491 independent reflections
Radiation source: INCOATEC high brilliance microfocus sealed tube	3692 reflections with I > 2σ(I)
Multilayer mirror monochromator	R_int = 0.042
φ and ω scans	θ_max = 28.3°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2016)	h = −11→11
T_min = 0.954, T_max = 0.980	k = −13→13
59876 measured reflections	l = −14→14

Refinement top

Refinement on F²	Primary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.120	w = 1/[σ²(F_o²) + (0.0452P)² + 0.7003P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
4491 reflections	Δρ_max = 0.43 e Å⁻³
255 parameters	Δρ_min = −0.43 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	0.07789 (14)	0.22664 (13)	0.15945 (11)	0.0204 (2)
C2	0.07976 (16)	0.36156 (15)	0.21549 (13)	0.0192 (3)
C3	0.16984 (15)	0.43512 (14)	0.34110 (13)	0.0171 (3)
C4	0.25843 (15)	0.36523 (14)	0.41074 (12)	0.0168 (3)
C4A	0.26008 (15)	0.21910 (14)	0.35031 (13)	0.0173 (3)
C5	0.34837 (17)	0.13520 (15)	0.40993 (14)	0.0216 (3)
H5	0.4093	0.1758	0.4944	0.026*
C6	0.34646 (18)	−0.00371 (16)	0.34678 (15)	0.0251 (3)
H6	0.4067	−0.0585	0.3877	0.030*
C7	0.25608 (19)	−0.06624 (15)	0.22177 (14)	0.0250 (3)
H7	0.2562	−0.1626	0.1789	0.030*
C8	0.16816 (18)	0.01086 (15)	0.16161 (14)	0.0232 (3)
H8	0.1067	−0.0323	0.0776	0.028*
C8A	0.16872 (16)	0.15504 (14)	0.22455 (13)	0.0187 (3)
C21	−0.01256 (19)	0.43927 (16)	0.13843 (14)	0.0251 (3)
H21A	−0.0605	0.3749	0.0530	0.038*
H21B	0.0581	0.5199	0.1310	0.038*
H21C	−0.0955	0.4737	0.1810	0.038*
C31	0.17896 (16)	0.59297 (14)	0.38398 (13)	0.0180 (3)
O31	0.29053 (12)	0.67679 (11)	0.38197 (10)	0.0231 (2)
O32	0.04628 (11)	0.62833 (10)	0.41672 (9)	0.0200 (2)
C32	0.03379 (17)	0.77805 (14)	0.44196 (14)	0.0207 (3)
H32A	−0.0788	0.7871	0.4320	0.025*
H32B	0.0773	0.8161	0.3786	0.025*
C33	0.12155 (18)	0.86413 (16)	0.57495 (14)	0.0250 (3)
H33A	0.0848	0.8219	0.6375	0.037*
H33B	0.1019	0.9616	0.5917	0.037*
H33C	0.2348	0.8646	0.5818	0.037*
C41	0.35128 (16)	0.43372 (14)	0.54207 (13)	0.0184 (3)
H41	0.4482	0.4038	0.5650	0.022*
C42	0.31086 (16)	0.53430 (15)	0.63157 (13)	0.0193 (3)
H42	0.2140	0.5648	0.6098	0.023*
C421	0.40671 (16)	0.60055 (15)	0.76133 (13)	0.0192 (3)
C422	0.52605 (17)	0.53948 (15)	0.81430 (13)	0.0213 (3)
H422	0.5451	0.4509	0.7667	0.026*
C423	0.61718 (17)	0.60661 (16)	0.93570 (14)	0.0236 (3)
H423	0.6985	0.5643	0.9707	0.028*
C424	0.58945 (17)	0.73547 (16)	1.00582 (13)	0.0228 (3)
C425	0.46796 (19)	0.79605 (16)	0.95666 (14)	0.0259 (3)
H425	0.4474	0.8832	1.0059	0.031*
C426	0.37692 (18)	0.72844 (16)	0.83523 (14)	0.0240 (3)
H426	0.2933	0.7695	0.8018	0.029*
C427	0.6902 (2)	0.81210 (18)	1.13510 (15)	0.0302 (3)
F471	0.74662 (16)	0.94629 (12)	1.14494 (11)	0.0523 (3)
F472	0.81434 (15)	0.75355 (14)	1.16419 (11)	0.0539 (4)
F473	0.61164 (15)	0.81641 (14)	1.22927 (10)	0.0506 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0231 (6)	0.0206 (6)	0.0159 (5)	0.0032 (4)	0.0012 (4)	0.0049 (4)
C2	0.0200 (6)	0.0198 (6)	0.0175 (6)	0.0032 (5)	0.0025 (5)	0.0061 (5)
C3	0.0170 (6)	0.0167 (6)	0.0178 (6)	0.0030 (5)	0.0044 (5)	0.0050 (5)
C4	0.0153 (6)	0.0176 (6)	0.0164 (6)	0.0014 (5)	0.0026 (5)	0.0045 (5)
C4A	0.0178 (6)	0.0166 (6)	0.0177 (6)	0.0027 (5)	0.0037 (5)	0.0054 (5)
C5	0.0227 (7)	0.0206 (7)	0.0203 (6)	0.0039 (5)	0.0015 (5)	0.0061 (5)
C6	0.0291 (7)	0.0198 (7)	0.0263 (7)	0.0070 (6)	0.0018 (6)	0.0079 (6)
C7	0.0311 (8)	0.0170 (6)	0.0250 (7)	0.0051 (6)	0.0050 (6)	0.0036 (5)
C8	0.0286 (7)	0.0201 (7)	0.0181 (6)	0.0030 (5)	0.0032 (5)	0.0023 (5)
C8A	0.0201 (6)	0.0187 (6)	0.0169 (6)	0.0028 (5)	0.0034 (5)	0.0053 (5)
C21	0.0292 (7)	0.0249 (7)	0.0196 (7)	0.0059 (6)	−0.0017 (5)	0.0080 (5)
C31	0.0192 (6)	0.0183 (6)	0.0166 (6)	0.0044 (5)	0.0024 (5)	0.0055 (5)
O31	0.0212 (5)	0.0190 (5)	0.0293 (5)	0.0034 (4)	0.0061 (4)	0.0070 (4)
O32	0.0183 (5)	0.0184 (5)	0.0230 (5)	0.0045 (4)	0.0043 (4)	0.0051 (4)
C32	0.0216 (6)	0.0184 (6)	0.0225 (7)	0.0072 (5)	0.0035 (5)	0.0057 (5)
C33	0.0271 (7)	0.0217 (7)	0.0236 (7)	0.0065 (6)	0.0028 (6)	0.0032 (5)
C41	0.0165 (6)	0.0186 (6)	0.0182 (6)	0.0005 (5)	0.0004 (5)	0.0055 (5)
C42	0.0181 (6)	0.0204 (6)	0.0177 (6)	0.0023 (5)	0.0011 (5)	0.0050 (5)
C421	0.0183 (6)	0.0207 (6)	0.0167 (6)	0.0015 (5)	0.0026 (5)	0.0038 (5)
C422	0.0215 (7)	0.0219 (7)	0.0191 (6)	0.0050 (5)	0.0034 (5)	0.0037 (5)
C423	0.0220 (7)	0.0288 (7)	0.0196 (7)	0.0068 (6)	0.0018 (5)	0.0069 (6)
C424	0.0234 (7)	0.0246 (7)	0.0164 (6)	0.0007 (5)	0.0013 (5)	0.0027 (5)
C425	0.0307 (8)	0.0207 (7)	0.0214 (7)	0.0047 (6)	0.0012 (6)	0.0004 (5)
C426	0.0250 (7)	0.0225 (7)	0.0212 (7)	0.0063 (5)	0.0001 (5)	0.0030 (5)
C427	0.0324 (8)	0.0313 (8)	0.0199 (7)	0.0023 (6)	−0.0023 (6)	0.0023 (6)
F471	0.0664 (8)	0.0348 (6)	0.0344 (6)	−0.0146 (5)	−0.0164 (5)	0.0025 (5)
F472	0.0479 (7)	0.0611 (8)	0.0335 (6)	0.0201 (6)	−0.0186 (5)	−0.0060 (5)
F473	0.0511 (7)	0.0703 (8)	0.0182 (5)	−0.0011 (6)	0.0044 (4)	−0.0003 (5)

Geometric parameters (Å, º) top

N1—C2	1.3168 (18)	C32—C33	1.511 (2)
N1—C8A	1.3720 (18)	C32—H32A	0.9900
C2—C3	1.4292 (18)	C32—H32B	0.9900
C2—C21	1.5021 (19)	C33—H33A	0.9800
C3—C4	1.3786 (18)	C33—H33B	0.9800
C3—C31	1.5014 (18)	C33—H33C	0.9800
C4—C4A	1.4322 (18)	C41—C42	1.3388 (19)
C4—C41	1.4774 (18)	C41—H41	0.9500
C4A—C5	1.4191 (19)	C42—C421	1.4701 (18)
C4A—C8A	1.4200 (18)	C42—H42	0.9500
C5—C6	1.369 (2)	C421—C422	1.3949 (19)
C5—H5	0.9500	C421—C426	1.400 (2)
C6—C7	1.409 (2)	C422—C423	1.3867 (19)
C6—H6	0.9500	C422—H422	0.9500
C7—C8	1.368 (2)	C423—C424	1.385 (2)
C7—H7	0.9500	C423—H423	0.9500
C8—C8A	1.4168 (19)	C424—C425	1.389 (2)
C8—H8	0.9500	C424—C427	1.497 (2)
C21—H21A	0.9800	C425—C426	1.387 (2)
C21—H21B	0.9800	C425—H425	0.9500
C21—H21C	0.9800	C426—H426	0.9500
C31—O31	1.2087 (17)	C427—F472	1.328 (2)
C31—O32	1.3342 (17)	C427—F471	1.332 (2)
O32—C32	1.4614 (16)	C427—F473	1.340 (2)

C2—N1—C8A	118.08 (12)	C33—C32—H32A	109.3
N1—C2—C3	122.90 (12)	O32—C32—H32B	109.3
N1—C2—C21	116.74 (12)	C33—C32—H32B	109.3
C3—C2—C21	120.30 (12)	H32A—C32—H32B	108.0
C4—C3—C2	120.52 (12)	C32—C33—H33A	109.5
C4—C3—C31	122.57 (12)	C32—C33—H33B	109.5
C2—C3—C31	116.42 (11)	H33A—C33—H33B	109.5
C3—C4—C4A	117.29 (12)	C32—C33—H33C	109.5
C3—C4—C41	123.40 (12)	H33A—C33—H33C	109.5
C4A—C4—C41	119.30 (12)	H33B—C33—H33C	109.5
C5—C4A—C8A	118.41 (12)	C42—C41—C4	125.72 (13)
C5—C4A—C4	123.25 (12)	C42—C41—H41	117.1
C8A—C4A—C4	118.35 (12)	C4—C41—H41	117.1
C6—C5—C4A	120.57 (13)	C41—C42—C421	124.22 (13)
C6—C5—H5	119.7	C41—C42—H42	117.9
C4A—C5—H5	119.7	C421—C42—H42	117.9
C5—C6—C7	120.64 (13)	C422—C421—C426	118.55 (13)
C5—C6—H6	119.7	C422—C421—C42	122.19 (13)
C7—C6—H6	119.7	C426—C421—C42	119.26 (13)
C8—C7—C6	120.48 (13)	C423—C422—C421	120.76 (13)
C8—C7—H7	119.8	C423—C422—H422	119.6
C6—C7—H7	119.8	C421—C422—H422	119.6
C7—C8—C8A	120.02 (13)	C424—C423—C422	119.87 (13)
C7—C8—H8	120.0	C424—C423—H423	120.1
C8A—C8—H8	120.0	C422—C423—H423	120.1
N1—C8A—C8	117.31 (12)	C423—C424—C425	120.37 (13)
N1—C8A—C4A	122.82 (12)	C423—C424—C427	120.69 (14)
C8—C8A—C4A	119.87 (12)	C425—C424—C427	118.94 (14)
C2—C21—H21A	109.5	C426—C425—C424	119.56 (14)
C2—C21—H21B	109.5	C426—C425—H425	120.2
H21A—C21—H21B	109.5	C424—C425—H425	120.2
C2—C21—H21C	109.5	C425—C426—C421	120.83 (14)
H21A—C21—H21C	109.5	C425—C426—H426	119.6
H21B—C21—H21C	109.5	C421—C426—H426	119.6
O31—C31—O32	124.46 (13)	F472—C427—F471	106.29 (15)
O31—C31—C3	123.44 (12)	F472—C427—F473	105.83 (14)
O32—C31—C3	111.98 (11)	F471—C427—F473	106.37 (14)
C31—O32—C32	116.34 (11)	F472—C427—C424	113.19 (14)
O32—C32—C33	111.65 (11)	F471—C427—C424	111.94 (13)
O32—C32—H32A	109.3	F473—C427—C424	112.70 (14)

C8A—N1—C2—C3	−1.0 (2)	C2—C3—C31—O31	−99.75 (16)
C8A—N1—C2—C21	176.13 (12)	C4—C3—C31—O32	−111.53 (14)
N1—C2—C3—C4	−1.0 (2)	C2—C3—C31—O32	76.46 (15)
C21—C2—C3—C4	−178.09 (13)	O31—C31—O32—C32	4.82 (19)
N1—C2—C3—C31	171.16 (13)	C3—C31—O32—C32	−171.35 (11)
C21—C2—C3—C31	−5.91 (19)	C31—O32—C32—C33	−80.77 (15)
C2—C3—C4—C4A	2.11 (19)	C3—C4—C41—C42	34.8 (2)
C31—C3—C4—C4A	−169.59 (12)	C4A—C4—C41—C42	−145.85 (14)
C2—C3—C4—C41	−178.53 (12)	C4—C41—C42—C421	−179.75 (12)
C31—C3—C4—C41	9.8 (2)	C41—C42—C421—C422	−17.7 (2)
C3—C4—C4A—C5	178.82 (13)	C41—C42—C421—C426	162.95 (14)
C41—C4—C4A—C5	−0.6 (2)	C426—C421—C422—C423	−2.4 (2)
C3—C4—C4A—C8A	−1.24 (19)	C42—C421—C422—C423	178.24 (13)
C41—C4—C4A—C8A	179.38 (12)	C421—C422—C423—C424	0.3 (2)
C8A—C4A—C5—C6	0.7 (2)	C422—C423—C424—C425	1.8 (2)
C4—C4A—C5—C6	−179.36 (13)	C422—C423—C424—C427	−177.82 (14)
C4A—C5—C6—C7	−0.4 (2)	C423—C424—C425—C426	−1.7 (2)
C5—C6—C7—C8	−0.3 (2)	C427—C424—C425—C426	177.92 (14)
C6—C7—C8—C8A	0.6 (2)	C424—C425—C426—C421	−0.5 (2)
C2—N1—C8A—C8	−178.55 (13)	C422—C421—C426—C425	2.5 (2)
C2—N1—C8A—C4A	1.9 (2)	C42—C421—C426—C425	−178.13 (14)
C7—C8—C8A—N1	−179.83 (14)	C423—C424—C427—F472	8.1 (2)
C7—C8—C8A—C4A	−0.3 (2)	C425—C424—C427—F472	−171.53 (15)
C5—C4A—C8A—N1	179.16 (13)	C423—C424—C427—F471	128.18 (17)
C4—C4A—C8A—N1	−0.8 (2)	C425—C424—C427—F471	−51.4 (2)
C5—C4A—C8A—C8	−0.3 (2)	C423—C424—C427—F473	−111.97 (17)
C4—C4A—C8A—C8	179.70 (12)	C425—C424—C427—F473	68.4 (2)
C4—C3—C31—O31	72.26 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C41—H41···O31ⁱ	0.95	2.54	3.4922 (18)	178
C422—H422···O31ⁱ	0.95	2.56	3.3924 (19)	146

Symmetry code: (i) −x+1, −y+1, −z+1.

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

Compound	C3—C4—C41—C42	C41—C42—C421—C422	C2—C3—C31—O31	C2—C3—C31—O32
(I)	46.40 (16)	13.78 (18)	66.18 (15)
(II)	46.8 (3)	14.8 (3)	68.2 (2)
(III)	49.0 (2)	13.0 (2)	69.52 (18)
(IV)	48.8 (2)	1.2 (3)	73.7 (2)	-104.85 (17)
(V)	51.4 (2)	10.6 (2)	-102.56 (17)	75.88 (15)
(VI)	34.8 (2)	-17.7 (2)	-99.75 (16)	76.46 (15)
(VII)	51.0 (5)	2.0 (5)	71.5 (4)
(VIII)	54.17 (19)	-4.0 (2)	-97.59 (15)

Hydrogen bonds and short intramolecular contacts (Å, °) for compounds (I)–(VIII). top

Compound	D—H···A	D—H	H···A	D···A	D—H···A
(I)	C41—H41···O31ⁱ	0.95	2.41	3.2527 (15)	148
	C426-H426···Cg3ⁱⁱ	0.95	2.77	3.5252 (13)	138
(II)	C41—H41···O31ⁱ	0.95	2.37	3.283 (2)	161
	C426—H426···Cg3ⁱⁱ	0.95	2.91	3.7071 (19)	142
(III)	C41—H41···O31ⁱ	0.95	2.42	3.3290 (17)	161
	C426—H426···Cg3ⁱⁱ	0.95	3.00	3.7621 (15)	138
(IV)	C32—H32B···O424ⁱⁱⁱ	0.99	2.57	3.406 (2)	142
	C423—H423···Cg1^iv	0.95	2.91	3.4894 (19)	120
(V)	C423—H423···O31^v	0.95	2.59	3.2197 (17)	124
	C426—H426···Cg1^iv	0.95	2.74	3.5961 (16)	151
(VI)	C41—H41···O31^iv	0.95	2.54	3.4922 (18)	178
	C422—H422···O31^iv	0.95	2.56	3.3924 (19)	146
(VII)	C41—H41···O31^vi	0.95	2.37	3.300 (5)	167
	C422—H422···O31^vi	0.95	2.57	3.506 (4)	169
	C426—H426···Cg4^vii	0.95	2.67	3.549 (4)	155
(VIII)	C334—H334···O31^viii	0.95	2.61	3.542 (2)	168
	C7—H7···Cg5^ix	0.95	2.93	3.6437 (16)	133
	C422—H422···Cg1^x	0.95	2.93	3.6300 (17)	132

Cg1, Cg3, Cg4 and Cg5 represent the centroids of the N1/C2–C4/C4A/C8A, C421–C426, C311–C316 [present in (VII) only] and C331–C336 [present in (VIII) only] rings, respectively; ring 2 comprises atoms C4A/C5–C8/C8A.

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

Acknowledgements

The authors thank 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 de la Universidad Industrial de Santander (proyecto No. 2497, to AP); Universidad de Jaén, the Consejería de Economía, Innovación, Ciencia y Empleo (Junta de Andalucía, Spain) and Centro de Instrumentación Científico–Técnica of the Universidad de Jaén (UJA) (to JC).

References

Acosta, L. M., Bahsas, A., Palma, A., Cobo, J., Hursthouse, M. B. & Glidewell, C. (2009). Acta Cryst. C65, o92–o96. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Blanco, M. C., Palma, A., Cobo, J. & Glidewell, C. (2012). Acta Cryst. C68, o195–o198. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (2016). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2017). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2018). APEX3. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bürgi, H. B., Dunitz, J. D., Lehn, J. M. & Wipff, M. (1974). Tetrahedron, 30, 1563–1572. Google Scholar
Chantrapromma, S., Kaewmanee, N., Boonnak, N., Quah, C. K. & Fun, H.-K. (2014). Acta Cryst. E70, o395–o396. CSD CrossRef IUCr Journals Google Scholar
Chantrapromma, S., Kobkeatthawin, T., Chanawanno, K., Karalai, S. & Fun, H.-K. (2008). Acta Cryst. E64, o876–o877. Web of Science CSD CrossRef IUCr Journals Google Scholar
Cieslik, W., Musiol, R., Nycz, J. E., Jampilek, J., Vejsova, M., Wolff, M., Machura, B. & Polanski, J. (2012). Bioorg. Med. Chem. 20, 6960–6968. Web of Science CrossRef CAS PubMed Google Scholar
El-Sayed, M. A.-A., El-Husseiny, W. M., Abdel-Aziz, N. I., El-Azab, A. S., Abuelizz, H. A. & Abdel-Aziz, A. A.-M. (2018). J. Enzyme Inhib. Med. Chem. 33, 199–209. Web of Science CAS PubMed Google Scholar
Etter, M. C. (1990). Acc. Chem. Res. 23, 120–126. CrossRef CAS Web of Science Google Scholar
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256–262. CrossRef ICSD CAS Web of Science IUCr Journals Google Scholar
Fun, H.-K., Kaewmanee, N., Chanawanno, K., Boonnak, N. & Chantrapromma, S. (2013). Acta Cryst. E69, o1510–o1511. CSD CrossRef CAS IUCr Journals Google Scholar
Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. Web of Science CrossRef IUCr Journals Google Scholar
Jasinski, J. P., Guild, C. J., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2010). Acta Cryst. E66, o1948–o1949. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Katritzsky, A. R., Meth-Cohn, O. & Rees, C. (1995). In Comprehensive Organic Functional Group Transformations. Oxford: Pergamon Press. Google Scholar
Kobkeatthawin, T., Ruanwas, P., Chantrapromma, S. & Fun, H.-K. (2008). Acta Cryst. E64, o642–o643. Web of Science CSD CrossRef IUCr Journals Google Scholar
Kobkeatthawin, T., Suwunwong, T., Chantrapromma, S. & Fun, H.-K. (2009). Acta Cryst. E65, o76–o77. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Kuz'mina, L. G., Sitin, A. G., Gulakova, E., Fedorova, O. A., Lermontova, E. K. & Churakov, A. V. (2012). Crystallogr. Rep. 57, 85–95. CAS Google Scholar
Meléndez, A., Plata, A., Rodríguez, R., Ardila, D., Guerrero, S. A., Acosta, L. M., Cobo, J., Nogueras, M. & Palma, A. (2020). Synthesis, 52, 1804–1822. Google Scholar
Nayak, P. S., Narayana, B., Yathirajan, H. S., Hosten, E. C., Betz, R. & Glidewell, C. (2014). Acta Cryst. C70, 1011–1016. Web of Science CSD CrossRef IUCr Journals Google Scholar
Omar, W. A. E. & Hormi, O. E. O. (2009). Tetrahedron, 65, 4422–4428. Web of Science CrossRef CAS Google Scholar
Polanski, J., Zouhiri, F., Jeanson, L., Desmaële, D., d'Angelo, J., Mouscadet, J. F., Gieleciak, R., Gasteiger, J. & Le Bret, M. (2002). J. Med. Chem. 45, 4647–4654. Web of Science CrossRef PubMed CAS Google Scholar
Roberts, B. F., Zheng, Y., Cleaveleand, J., Lee, S., Lee, E., Ayong, L., Yuan, Y. & Chakrabarti, D. (2017). Int. J. Parasitol. Drugs Drug Resist. 7, 120–129. Web of Science CrossRef PubMed Google Scholar
Samshuddin, S., Jasinski, J. P., Golen, J. A., Narayana, B., Yathirajan, H. S. & Glidewell, C. (2014). Acta Cryst. C70, 867–871. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sharma, R., Kumar, R., Kumar, I. & Sharma, U. (2015). Eur. J. Org. Chem. 2015, 7519–7528. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Spek, A. L. (2015). Acta Cryst. C71, 9–18. Web of Science CrossRef IUCr Journals Google Scholar
Spek, A. L. (2020). Acta Cryst. E76, 1–11. Web of Science CrossRef IUCr Journals Google Scholar
Valle, G., Busetti, V. & Galiazzo, G. (1986). Z. Kristallogr. 177, 315–318. CrossRef CAS Web of Science Google Scholar
Wang, X. Q., Xia, C. L., Chen, S. B., Tan, J. H., Ou, T. M., Huang, S. L., Li, D., Gu, L. Q. & Huang, Z. S. (2015). Eur. J. Med. Chem. 89, 349–361. Web of Science CrossRef CAS PubMed Google Scholar
Wood, P. A., Allen, F. H. & Pidcock, E. (2009). CrystEngComm, 11, 1563–1571. Web of Science CrossRef CAS Google Scholar
Xia, H., Liu, Y., Zhao, P., Gou, S. & Wang, J. (2016). Org. Lett. 18, 1796–1799. Web of Science CrossRef CAS PubMed Google Scholar

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

STRUCTURAL
CHEMISTRY

ISSN: 2053-2296

Volume 76| Part 9| September 2020| Pages 883-890

https://doi.org/10.1107/S2053229620010803

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text
		Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text
		Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

4-Styryl­quino­lines from cyclo­condensation reactions between (2-amino­phen­yl)chalcones and 1,3-diketones: crystal structures and regiochemistry

1. Introduction

2. Experimental

2.1. Synthesis and crystallization

2.2. Refinement

3. Results and discussion

Supporting information

Acknowledgements

Funding information

References

research papers

4-Styrylquinolines from cyclocondensation reactions between (2-aminophenyl)chalcones and 1,3-diketones: crystal structures and regiochemistry