The hydrogen-bonding interactions in the crystal structures of N-(5-acetyl-2-methylphenyl)quinoline-2-carboxamide, N-(5-acetyl-2-bromophenyl)quinoline-2-carboxamide and N-(5-acetyl-2-ethynylphenyl)quinoline-2-carboxamide are described. The latter two compounds also exhibit π–π interactions.
Keywords: crystal structure, quinoline, carboxamide, acetophenone.
Abstract
In the title compounds, N-(5-acetyl-2-methylphenyl)quinoline-2-carboxamide [C19H16N2O2, (I)], N-(5-acetyl-2-bromophenyl)quinoline-2-carboxamide [C18H13BrN2O2, (II)] and N-(5-acetyl-2-ethynylphenyl)quinoline-2-carboxamide [C20H14N2O2, (III)], the quinoline ring system is essentially planar and forms a dihedral angles of 3.68 (5) (I), 5.59 (7) (II) and 1.87 (6)° (III) with the acetyl-substituted ring. The molecular structures of (I) and (III) each feature an intramolecular N—H⋯N hydrogen bond, forming an S(5) ring, while in (II) an intramolecular bifurcated N—H⋯(N,Br) hydrogen bond forms two S(5) rings. In the crystals, weak C—H⋯O hydrogen bonds link molecules of (I) into C(7) chains long [010], molecules of (II) into chains of R 2 2(8) rings along [110] and molecules of (III) into C(8) chains along [010]. In (I), there are no significant π–π stacking interactions under 4 Å, but in both (II) and (III), π–π interactions link the weak hydrogen-bonded chains into layers parallel to (001) [centroid–centroid disttances of 3.748 (1) Å in (II) and 3.577 (1), 3.784 (1) and 3.780 (1) Å in (III)].
Chemical context
Aminoacetophenones, quinolines and carboxamides have been reported to possess many interesting pharmacological activities and they are characteristic components of a large number of biologically active compounds. The wide spectrum of biological effects of these kind of compounds includes antimicrobial (Nawar & Hosny, 2000 ▸), anticonvulsant (Pandeya et al., 1998 ▸), cytotoxic (Zhao et al., 2005 ▸), anti-malarial (Egan et al., 1994 ▸), antiproliferative (Chen et al., 2006 ▸), antituberculosis/antimycobacterial (Gonec et al., 2012 ▸) activities, radioligands (Matarrese et al., 2001 ▸, Belloli et al., 2004 ▸), calpain inhibitors (Nam et al., 2008 ▸), TPSO ligand (Blair et al., 2013 ▸) and pharmaceutical medicaments (Weidmann et al., 2008 ▸), among others.
Structural commentary
The molecular structure of title compounds (I), (II) and (III) are shown in Figs. 1 ▸, 2 ▸ and 3 ▸, respectively. The quinoline ring system [C1–C9/N1 in (I), C2–C10/N1 in (II) and C12–C20/N2 in (III)] in each compound is essentially planar with maximum deviations of 0.015 (1) Å for C3 in (I), 0.017 (2) Å for C3 in (II) and 0.013 (2) Å for C17 in (III). The quinoline ring system forms dihedral angles of 3.68 (5)° (I), 5.59 (7)° (II) and 1.87 (6)° (III) with the acetyl-substituted ring [C11–C16 in (I) and (II), C3–C8 in (III)]. In the molecular structures of (I) and (III), an intramolecular N—H⋯N hydrogen bond forms an S(5) ring while in (II) an intramolecular bifurcated N—H⋯(N,Br) hydrogen bond forms two S(5) rings (Tables 1 ▸–3 ▸
▸).
Figure 1.
The molecular structure of (I), with the atom-numbering scheme and displacement ellipsoids drawn at the 50% probability level.
Figure 2.
The molecular structure of (II), with the atom-numbering scheme and displacement ellipsoids drawn at the 50% probability level.
Figure 3.
The molecular structure of (III), with the-atom numbering scheme and displacement ellipsoids drawn at the 50% probability level.
Table 1. Hydrogen-bond geometry (Å, °) for (I) .
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| N2—H2⋯N1 | 0.86 | 2.15 | 2.619 (2) | 114 |
| C17—H17⋯O1i | 0.96 | 2.49 | 3.424 (2) | 164 |
Symmetry code: (i) 
.
Table 2. Hydrogen-bond geometry (Å, °) for (II) .
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| N2—H2⋯N1 | 0.86 | 2.19 | 2.629 (2) | 112 |
| C3—H3⋯O1i | 0.93 | 2.55 | 3.410 (2) | 154 |
| C18—H18⋯O2ii | 0.96 | 2.49 | 3.444 (2) | 171 |
| N2—H2⋯Br1 | 0.86 | 2.58 | 3.081 (1) | 118 |
Symmetry codes: (i) 
; (ii) 
.
Table 3. Hydrogen-bond geometry (Å, °) for (III) .
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| N1—H1⋯N2 | 0.86 | 2.23 | 2.666 (2) | 111 |
| C10—H10⋯O2i | 0.93 | 2.36 | 3.103 (2) | 136 |
Symmetry code: (i) 
.
Supramolecular features
In the crystals, weak C—H⋯O hydrogen bonds link molecules of (I) into C(7) chains along [010] (Fig. 4 ▸), molecules of (II) into chains of 
(8) rings along [110] (Fig. 5 ▸) and molecules of (III) into C(8) chains along [010] (Fig. 6 ▸). In (I), there are no significant π–π stacking interactions under 4 Å but in (II) π–π interactions link the weak hydrogen-bonded chains into layers parallel to (001) [centroid–centroid distance Cg1⋯Cg2(1 + x, y, z) = 3.748 (1) Å; Cg1 and Cg2 are the centroids of the C5–C10 and N1/C2–C6 rings, respectively]. In (III), π–π interactions link the weak hydrogen-bonded chains into layers parallel to (001) with centroid–centroid distances Cg3⋯Cg4(−1 + x, −1 + y, −1 + z) = 3.577 (1), Cg4⋯Cg5(−x + 1, −y + 1, −z + 1) 3.784 (1) and Cg4⋯Cg5(−x + 2, −y + 1, −z + 1) = 3.780 (1) Å; Cg3, Cg4, and Cg5 are the centroids of the N2/C12–C16, C3–C8 and C15–C20 rings, respectively].
Figure 4.
Part of the crystal structure of (I), with intermolecular and intramolecular hydrogen bonds shown as black dotted lines. Only H atoms involved in hydrogen bonds are shown.
Figure 5.
Part of the crystal structure of (II), with intermolecular and intramolecular hydrogen bonds shown as black dotted lines. Only H atoms involved in hydrogen bonds are shown.
Figure 6.
Part of the crystal structure of (III), with intermolecular and intramolecular hydrogen bonds shown as black dotted lines. Only H atoms involved in hydrogen bonds are shown.
Database survey
A search of the Cambridge Structural Database (Groom et al. 2016 ▸; Version 1.18, April 2016) for similar compounds with an N-phenylquinoline-2-carboxamide skeleton resulted in twelve hits. One entry for the compound without substituents is reported (Jing & Qin, 2007 ▸). Eight are structures substituted in the 4-position of the phenyl group: one methoxy group (Qi et al., 2003 ▸) and another a nitro group (Jing & Qin, 2008 ▸); one chlorine and one fluorine (Khavasi et al., 2014 ▸), and two reports each for bromine (Bobal et al., 2012 ▸; Khavasi et al., 2014 ▸) and iodine (Qi et al., 2003 ▸; Khavasi et al., 2014 ▸). The rest have large organic substituents.
Synthesis and crystallization
Compounds (I)–(III) were prepared by refluxing a mixture of quinaldic acid, triethylamine, p-toluenesulfonyl chloride and the corresponding substituted aminoacetophenones (1a–c) for 24 h in DCM (Fig. 7 ▸). Acetic acid 5% was added to quench the reaction, and the organic phase was washed three times with water. After evaporation of DCM, the compounds were purified by silica column chromatography (pentane:ethyl acetate 2:1). Single crystals were obtained by slow evaporation of the respective solutions of the compounds in dichloromethane into a closed flask with petroleum ether.
Figure 7.
The reaction scheme for the synthesis of the title compounds
N -(5-acetyl-2-methylphenyl)quinoline-2-carboxamide (I): Light-yellow solid (0.700 g, yield quant, R f PE/EA 2:1 0.52). 1H NMR (400 MHz, CDCl3): δ 8.95 (d, 3J = 7.7 Hz, 1H, quinol), 8.40 (s, 2H, ArH quinol), 8.17 (d, 3J = 8.5 Hz, 1H, ArH), 7.93 (d, 3J = 9.0 Hz, 1H, quinol), 7.82 (ddd, 3J = 8.4, 3J = 6.9 Hz, 1H, quinol), 7.73 (dd, 3J = 7.9, 1H, ArH), 7.67 (ddd, 3J = 8.1, 3J = 6.9 Hz, 1H, quinol), 7.35 (d, 3J = 7.9 Hz, 1H, quinol), 2.65 (s, 3H, CH3), 2.55 (s, 3H, COCH3). 13C NMR (100 MHz, CDCl3): δ 197.8 (Cquat), 162.2 (Cquat), 149.5 (Cquat), 146.2 (Cquat), 138.0 (Cquat), 136.2 (Cquat), 133.5 (Cquat), 130.7 (Cquat), 130.4 (+), 129.8 (+), 129.5 (+), 128.3 (+), 127.8 (+), 124.1 (+), 121.5 (+), 118.6 (+), 26.7 (+), 18.0 (+).
N -(5-acetyl-2-bromophenyl)quinoline-2-carboxamide (II): Yellow solid (0.700 g, yield quant, R f PE/EA 2:1 0.60). 1H NMR (400 MHz, CDCl3): δ 9.32 (s, 1H), 8.40 (d, 3J = 3.0 Hz, 2H), 8.23 (d, 3J = 8.5 Hz, 1H), 7.94 (d, 3J = 8.8 Hz, 1H), 7.83 (t, 3J = 7.0 Hz, 1H), 7.69 (m, 3H), 2.68 (s, 3H, COCH3). 13C NMR (100 MHz, CDCl3): δ 197.3 (Cquat), 162.6 (Cquat), 149.1 (Cquat), 146.3 (Cquat), 138.2 (Cquat), 137.2 (Cquat), 136.3 (Cquat), 132.8 (+), 130.6 (+), 130.5 (+), 130.6 (+), 128.5 (+), 127.8 (+), 124.1 (+), 121.1 (+), 118.9 (+), 118.5 (+), 26.7 (+).
N -(5-acetyl-2-ethynylphenyl)quinoline-2-carboxamide (III): Light-brown solid (0.700 g, yield quant, R f PE/EA 2:1 0.20). 1H NMR (400 MHz, CDCl3): δ 9.36 (d, 3J = 1.6 Hz, 1H), 8.40 (s, 2H), 8.15 (d, 3J = 8.5 Hz, 1H), 7.94 (d, 3J = 8.2 Hz, 1H), 7.82 (dd, 3J = 11.2, 4.2 Hz, 1H), 7.73 (dd, 3J = 8.1, 3J = 1.7 Hz, 1H), 7.71 (m, 1H), 7.63 (d, J = 8.1 Hz, 1H), 3.87 (s, 1H, CCH), 2.70 (s, 3H, CH3). 13C NMR (100 MHz, CDCl3): δ = 197.6 (Cquat), 162.8 (Cquat), 149.2 (Cquat), 146.3 (Cquat), 140.1 (Cquat), 138.0 (Cquat), 132.5 (+), 130.4 (+), 129.9 (+), 129.5 (+), 128.4 (+), 127.8 (+), 122.6 (+), 119.1 (+), 118.6 (+), 115.7 (+), 87.1 (Cquat), 79.0 (+), 26.8 (+).
Refinement
Crystal data, data collection and structure refinement details are summarized in Table 4 ▸. All non-hydrogen atoms were refined anisotropically. Hydrogen-atom positions were calculated geometrically and refined using the riding model. N–H = 0.86 Å, C—H = 0.96 Å for methyl H atoms and 0.93 Å for all other; U iso(H) = 1.2U eq(C,N) or 1.5U eq(Cmethyl).
Table 4. Experimental details.
| (I) | (II) | (III) | |
|---|---|---|---|
| Crystal data | |||
| Chemical formula | C19H16N2O2 | C18H13BrN2O2 | C20H14N2O2 |
| M r | 304.34 | 369.21 | 314.33 |
| Crystal system, space group | Monoclinic, P21/c | Triclinic, P
|
Triclinic, P
|
| Temperature (K) | 123 | 123 | 123 |
| a, b, c (Å) | 4.5787 (2), 14.7986 (7), 22.3732 (12) | 4.29848 (12), 11.6353 (3), 15.5888 (4) | 7.3075 (6), 8.2605 (4), 13.8196 (9) |
| α, β, γ (°) | 90, 92.130 (5), 90 | 103.788 (2), 95.515 (2), 96.195 (2) | 92.734 (5), 100.608 (6), 108.989 (6) |
| V (Å3) | 1514.93 (12) | 746.76 (3) | 770.11 (10) |
| Z | 4 | 2 | 2 |
| Radiation type | Cu Kα | Cu Kα | Mo Kα |
| μ (mm−1) | 0.71 | 3.85 | 0.09 |
| Crystal size (mm) | 0.33 × 0.12 × 0.07 | 0.65 × 0.10 × 0.06 | 0.19 × 0.08 × 0.05 |
| Data collection | |||
| Diffractometer | Agilent TitanS2 GV1000 | Agilent TitanS2 GV1000 | Agilent SuperNova Single source at offset, Eos |
| Absorption correction | Analytical [CrysAlis PRO (Rigaku OD, 2015 ▸), based on expressions derived by Clark & Reid (1995 ▸)] | Gaussian [CrysAlis PRO (Rigaku OD, 2015 ▸), based on expressions derived by Clark & Reid (1995 ▸)] | Analytical [CrysAlis PRO (Rigaku OD, 2015 ▸), based on expressions derived by Clark & Reid (1995 ▸)] |
| T min, T max | 0.869, 0.958 | 0.540, 0.900 | 0.987, 0.996 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 6056, 2935, 2562 | 12899, 2966, 2870 | 20693, 5173, 3687 |
| R int | 0.020 | 0.033 | 0.060 |
| (sin θ/λ)max (Å−1) | 0.625 | 0.622 | 0.753 |
| Refinement | |||
| R[F 2 > 2σ(F 2)], wR(F 2), S | 0.038, 0.106, 1.04 | 0.024, 0.065, 1.05 | 0.056, 0.151, 1.04 |
| No. of reflections | 2935 | 2966 | 5173 |
| No. of parameters | 210 | 210 | 218 |
| H-atom treatment | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.20, −0.21 | 0.48, −0.65 | 0.42, −0.26 |
Supplementary Material
Crystal structure: contains datablock(s) I, II, III. DOI: 10.1107/S2056989017006272/lh5839sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989017006272/lh5839Isup2.hkl
Structure factors: contains datablock(s) II. DOI: 10.1107/S2056989017006272/lh5839IIsup3.hkl
Structure factors: contains datablock(s) III. DOI: 10.1107/S2056989017006272/lh5839IIIsup4.hkl
Supporting information file. DOI: 10.1107/S2056989017006272/lh5839Isup5.cml
Supporting information file. DOI: 10.1107/S2056989017006272/lh5839IIsup6.cml
Supporting information file. DOI: 10.1107/S2056989017006272/lh5839IIIsup7.cml
Additional supporting information: crystallographic information; 3D view; checkCIF report
Acknowledgments
We are grateful to the University of Regensburg, Universidad Nacional de Colombia, DAAD and COLCIENCIAS (grant No. 49575) for financial support.
supplementary crystallographic information
(I) N-(5-Acetyl-2-methylphenyl)quinoline-2-carboxamide . Crystal data
| C19H16N2O2 | F(000) = 640 |
| Mr = 304.34 | Dx = 1.334 Mg m−3 |
| Monoclinic, P21/c | Cu Kα radiation, λ = 1.54184 Å |
| a = 4.5787 (2) Å | Cell parameters from 3477 reflections |
| b = 14.7986 (7) Å | θ = 6.0–74.2° |
| c = 22.3732 (12) Å | µ = 0.71 mm−1 |
| β = 92.130 (5)° | T = 123 K |
| V = 1514.93 (12) Å3 | Block, dark gray |
| Z = 4 | 0.33 × 0.12 × 0.07 mm |
(I) N-(5-Acetyl-2-methylphenyl)quinoline-2-carboxamide . Data collection
| Agilent TitanS2 GV1000 diffractometer | 2935 independent reflections |
| Radiation source: gradient vaccum rotating-anode X-ray tube, GV1000 (Cu) X-ray Source | 2562 reflections with I > 2σ(I) |
| Mirror monochromator | Rint = 0.020 |
| Detector resolution: 4.1818 pixels mm-1 | θmax = 74.4°, θmin = 3.6° |
| ω scans | h = −5→5 |
| Absorption correction: analytical [CrysAlis PRO (Rigaku OD, 2015), based on expressions derived by Clark & Reid (1995)] | k = −18→17 |
| Tmin = 0.869, Tmax = 0.958 | l = −27→21 |
| 6056 measured reflections |
(I) N-(5-Acetyl-2-methylphenyl)quinoline-2-carboxamide . Refinement
| Refinement on F2 | 0 restraints |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.038 | H-atom parameters constrained |
| wR(F2) = 0.106 | w = 1/[σ2(Fo2) + (0.0608P)2 + 0.2546P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.04 | (Δ/σ)max < 0.001 |
| 2935 reflections | Δρmax = 0.20 e Å−3 |
| 210 parameters | Δρmin = −0.21 e Å−3 |
(I) N-(5-Acetyl-2-methylphenyl)quinoline-2-carboxamide . Special details
| Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
(I) N-(5-Acetyl-2-methylphenyl)quinoline-2-carboxamide . Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| O1 | 0.59998 (18) | 0.50983 (6) | 0.24602 (4) | 0.0250 (2) | |
| O2 | 1.4993 (2) | 0.62002 (8) | 0.05885 (5) | 0.0410 (3) | |
| N2 | 0.7067 (2) | 0.65842 (7) | 0.26763 (5) | 0.0217 (2) | |
| H2 | 0.6628 | 0.7001 | 0.2925 | 0.026* | |
| N1 | 0.3450 (2) | 0.65936 (7) | 0.35561 (5) | 0.0223 (2) | |
| C10 | 0.5705 (2) | 0.57873 (8) | 0.27553 (5) | 0.0197 (2) | |
| C9 | 0.3690 (2) | 0.58150 (8) | 0.32767 (5) | 0.0200 (2) | |
| C16 | 1.0023 (2) | 0.62534 (8) | 0.18077 (5) | 0.0225 (3) | |
| H16 | 0.9290 | 0.5668 | 0.1784 | 0.027* | |
| C11 | 0.9095 (2) | 0.68391 (8) | 0.22502 (5) | 0.0205 (3) | |
| C12 | 1.0191 (2) | 0.77271 (8) | 0.22953 (6) | 0.0223 (3) | |
| C8 | 0.2199 (2) | 0.50181 (8) | 0.34310 (6) | 0.0229 (3) | |
| H8 | 0.2444 | 0.4485 | 0.3219 | 0.028* | |
| C15 | 1.2058 (2) | 0.65473 (8) | 0.13999 (6) | 0.0239 (3) | |
| C6 | 0.1639 (2) | 0.66364 (9) | 0.40278 (5) | 0.0242 (3) | |
| C17 | 0.9276 (3) | 0.83545 (8) | 0.27837 (6) | 0.0257 (3) | |
| H17A | 0.7217 | 0.8470 | 0.2739 | 0.039* | |
| H17B | 1.0329 | 0.8913 | 0.2758 | 0.039* | |
| H17C | 0.9700 | 0.8080 | 0.3166 | 0.039* | |
| C13 | 1.2190 (3) | 0.80052 (8) | 0.18796 (6) | 0.0252 (3) | |
| H13 | 1.2917 | 0.8592 | 0.1899 | 0.030* | |
| C14 | 1.3123 (3) | 0.74284 (9) | 0.14374 (6) | 0.0268 (3) | |
| H14 | 1.4464 | 0.7630 | 0.1165 | 0.032* | |
| C7 | 0.0383 (3) | 0.50538 (9) | 0.39030 (6) | 0.0260 (3) | |
| H7 | −0.0619 | 0.4539 | 0.4018 | 0.031* | |
| C5 | 0.0036 (2) | 0.58715 (9) | 0.42139 (6) | 0.0256 (3) | |
| C18 | 1.3186 (3) | 0.59328 (9) | 0.09298 (6) | 0.0284 (3) | |
| C1 | 0.1359 (3) | 0.74684 (10) | 0.43341 (6) | 0.0309 (3) | |
| H1 | 0.2429 | 0.7969 | 0.4218 | 0.037* | |
| C4 | −0.1839 (3) | 0.59647 (11) | 0.47008 (6) | 0.0337 (3) | |
| H4 | −0.2897 | 0.5469 | 0.4830 | 0.040* | |
| C3 | −0.2098 (3) | 0.67783 (12) | 0.49810 (6) | 0.0395 (4) | |
| H3 | −0.3356 | 0.6835 | 0.5296 | 0.047* | |
| C2 | −0.0478 (3) | 0.75369 (11) | 0.47989 (7) | 0.0371 (3) | |
| H2A | −0.0665 | 0.8085 | 0.4997 | 0.045* | |
| C19 | 1.2077 (4) | 0.49817 (10) | 0.08911 (8) | 0.0446 (4) | |
| H19A | 1.2992 | 0.4673 | 0.0570 | 0.067* | |
| H19B | 0.9998 | 0.4988 | 0.0818 | 0.067* | |
| H19C | 1.2530 | 0.4674 | 0.1261 | 0.067* |
(I) N-(5-Acetyl-2-methylphenyl)quinoline-2-carboxamide . Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0249 (4) | 0.0214 (4) | 0.0291 (5) | 0.0003 (3) | 0.0072 (3) | −0.0016 (3) |
| O2 | 0.0414 (5) | 0.0441 (6) | 0.0388 (6) | −0.0028 (4) | 0.0208 (4) | 0.0001 (5) |
| N2 | 0.0217 (5) | 0.0199 (5) | 0.0239 (5) | 0.0002 (4) | 0.0055 (4) | −0.0005 (4) |
| N1 | 0.0195 (5) | 0.0248 (5) | 0.0226 (5) | 0.0028 (4) | 0.0008 (4) | 0.0000 (4) |
| C10 | 0.0152 (5) | 0.0210 (5) | 0.0228 (6) | 0.0018 (4) | 0.0002 (4) | 0.0018 (4) |
| C9 | 0.0163 (5) | 0.0233 (5) | 0.0202 (6) | 0.0018 (4) | −0.0006 (4) | 0.0015 (4) |
| C16 | 0.0197 (5) | 0.0229 (5) | 0.0250 (6) | 0.0013 (4) | 0.0017 (4) | 0.0028 (5) |
| C11 | 0.0159 (5) | 0.0229 (5) | 0.0226 (6) | 0.0009 (4) | 0.0008 (4) | 0.0050 (4) |
| C12 | 0.0188 (5) | 0.0222 (6) | 0.0258 (6) | 0.0021 (4) | −0.0014 (4) | 0.0035 (5) |
| C8 | 0.0201 (5) | 0.0246 (6) | 0.0240 (6) | −0.0003 (4) | 0.0007 (4) | 0.0011 (5) |
| C15 | 0.0200 (5) | 0.0277 (6) | 0.0242 (6) | 0.0030 (4) | 0.0028 (4) | 0.0047 (5) |
| C6 | 0.0197 (5) | 0.0316 (6) | 0.0210 (6) | 0.0051 (5) | −0.0010 (4) | 0.0006 (5) |
| C17 | 0.0275 (6) | 0.0211 (5) | 0.0286 (6) | −0.0011 (5) | 0.0017 (5) | 0.0013 (5) |
| C13 | 0.0217 (5) | 0.0228 (5) | 0.0312 (7) | −0.0023 (4) | 0.0002 (5) | 0.0072 (5) |
| C14 | 0.0216 (6) | 0.0308 (6) | 0.0283 (7) | 0.0000 (5) | 0.0050 (5) | 0.0081 (5) |
| C7 | 0.0201 (5) | 0.0322 (6) | 0.0256 (6) | −0.0028 (5) | 0.0008 (5) | 0.0050 (5) |
| C5 | 0.0185 (5) | 0.0377 (7) | 0.0205 (6) | 0.0034 (5) | −0.0002 (4) | 0.0038 (5) |
| C18 | 0.0246 (6) | 0.0340 (7) | 0.0268 (6) | 0.0034 (5) | 0.0057 (5) | 0.0039 (5) |
| C1 | 0.0310 (6) | 0.0346 (7) | 0.0270 (7) | 0.0079 (5) | −0.0014 (5) | −0.0046 (5) |
| C4 | 0.0243 (6) | 0.0522 (8) | 0.0249 (7) | 0.0045 (6) | 0.0047 (5) | 0.0061 (6) |
| C3 | 0.0304 (7) | 0.0648 (10) | 0.0236 (7) | 0.0138 (7) | 0.0054 (5) | −0.0011 (7) |
| C2 | 0.0360 (7) | 0.0479 (8) | 0.0273 (7) | 0.0147 (6) | −0.0015 (5) | −0.0097 (6) |
| C19 | 0.0536 (9) | 0.0348 (8) | 0.0472 (9) | −0.0030 (6) | 0.0261 (7) | −0.0092 (7) |
(I) N-(5-Acetyl-2-methylphenyl)quinoline-2-carboxamide . Geometric parameters (Å, º)
| O1—C10 | 1.2249 (15) | C17—H17A | 0.9600 |
| O2—C18 | 1.2129 (17) | C17—H17B | 0.9600 |
| N2—H2 | 0.8600 | C17—H17C | 0.9600 |
| N2—C10 | 1.3490 (15) | C13—H13 | 0.9300 |
| N2—C11 | 1.4068 (15) | C13—C14 | 1.3861 (19) |
| N1—C9 | 1.3175 (15) | C14—H14 | 0.9300 |
| N1—C6 | 1.3674 (16) | C7—H7 | 0.9300 |
| C10—C9 | 1.5142 (16) | C7—C5 | 1.4075 (19) |
| C9—C8 | 1.4120 (16) | C5—C4 | 1.4188 (18) |
| C16—H16 | 0.9300 | C18—C19 | 1.498 (2) |
| C16—C11 | 1.3940 (17) | C1—H1 | 0.9300 |
| C16—C15 | 1.3973 (17) | C1—C2 | 1.365 (2) |
| C11—C12 | 1.4090 (16) | C4—H4 | 0.9300 |
| C12—C17 | 1.5051 (17) | C4—C3 | 1.365 (2) |
| C12—C13 | 1.3912 (17) | C3—H3 | 0.9300 |
| C8—H8 | 0.9300 | C3—C2 | 1.414 (2) |
| C8—C7 | 1.3694 (17) | C2—H2A | 0.9300 |
| C15—C14 | 1.3937 (18) | C19—H19A | 0.9600 |
| C15—C18 | 1.4970 (18) | C19—H19B | 0.9600 |
| C6—C5 | 1.4200 (18) | C19—H19C | 0.9600 |
| C6—C1 | 1.4172 (18) | ||
| C10—N2—H2 | 115.0 | C12—C13—H13 | 119.2 |
| C10—N2—C11 | 130.05 (10) | C14—C13—C12 | 121.53 (11) |
| C11—N2—H2 | 115.0 | C14—C13—H13 | 119.2 |
| C9—N1—C6 | 118.07 (10) | C15—C14—H14 | 119.9 |
| O1—C10—N2 | 126.59 (11) | C13—C14—C15 | 120.17 (11) |
| O1—C10—C9 | 121.36 (10) | C13—C14—H14 | 119.9 |
| N2—C10—C9 | 112.04 (10) | C8—C7—H7 | 120.1 |
| N1—C9—C10 | 116.96 (10) | C8—C7—C5 | 119.81 (11) |
| N1—C9—C8 | 124.38 (11) | C5—C7—H7 | 120.1 |
| C8—C9—C10 | 118.66 (10) | C7—C5—C6 | 118.13 (11) |
| C11—C16—H16 | 120.1 | C7—C5—C4 | 123.06 (12) |
| C11—C16—C15 | 119.89 (11) | C4—C5—C6 | 118.81 (12) |
| C15—C16—H16 | 120.1 | O2—C18—C15 | 120.37 (13) |
| N2—C11—C12 | 116.35 (10) | O2—C18—C19 | 120.53 (13) |
| C16—C11—N2 | 122.74 (11) | C15—C18—C19 | 119.10 (11) |
| C16—C11—C12 | 120.91 (11) | C6—C1—H1 | 119.9 |
| C11—C12—C17 | 121.28 (11) | C2—C1—C6 | 120.15 (14) |
| C13—C12—C11 | 118.00 (11) | C2—C1—H1 | 119.9 |
| C13—C12—C17 | 120.71 (11) | C5—C4—H4 | 119.9 |
| C9—C8—H8 | 121.0 | C3—C4—C5 | 120.25 (14) |
| C7—C8—C9 | 118.00 (11) | C3—C4—H4 | 119.9 |
| C7—C8—H8 | 121.0 | C4—C3—H3 | 119.6 |
| C16—C15—C18 | 121.71 (11) | C4—C3—C2 | 120.85 (13) |
| C14—C15—C16 | 119.50 (12) | C2—C3—H3 | 119.6 |
| C14—C15—C18 | 118.77 (11) | C1—C2—C3 | 120.34 (14) |
| N1—C6—C5 | 121.61 (11) | C1—C2—H2A | 119.8 |
| N1—C6—C1 | 118.80 (12) | C3—C2—H2A | 119.8 |
| C1—C6—C5 | 119.59 (12) | C18—C19—H19A | 109.5 |
| C12—C17—H17A | 109.5 | C18—C19—H19B | 109.5 |
| C12—C17—H17B | 109.5 | C18—C19—H19C | 109.5 |
| C12—C17—H17C | 109.5 | H19A—C19—H19B | 109.5 |
| H17A—C17—H17B | 109.5 | H19A—C19—H19C | 109.5 |
| H17A—C17—H17C | 109.5 | H19B—C19—H19C | 109.5 |
| H17B—C17—H17C | 109.5 | ||
| O1—C10—C9—N1 | −178.04 (10) | C11—C16—C15—C14 | −0.49 (18) |
| O1—C10—C9—C8 | 1.81 (16) | C11—C16—C15—C18 | 178.04 (11) |
| N2—C10—C9—N1 | 2.76 (14) | C11—C12—C13—C14 | −0.89 (17) |
| N2—C10—C9—C8 | −177.40 (10) | C12—C13—C14—C15 | 0.12 (19) |
| N2—C11—C12—C17 | 1.36 (16) | C8—C7—C5—C6 | −0.83 (17) |
| N2—C11—C12—C13 | −179.66 (10) | C8—C7—C5—C4 | 178.99 (11) |
| N1—C9—C8—C7 | −0.09 (18) | C15—C16—C11—N2 | −179.62 (10) |
| N1—C6—C5—C7 | 0.80 (17) | C15—C16—C11—C12 | −0.31 (17) |
| N1—C6—C5—C4 | −179.03 (11) | C6—N1—C9—C10 | 179.88 (9) |
| N1—C6—C1—C2 | 178.65 (12) | C6—N1—C9—C8 | 0.04 (17) |
| C10—N2—C11—C16 | 0.95 (19) | C6—C5—C4—C3 | 0.34 (18) |
| C10—N2—C11—C12 | −178.39 (11) | C6—C1—C2—C3 | 0.4 (2) |
| C10—C9—C8—C7 | −179.93 (10) | C17—C12—C13—C14 | 178.09 (11) |
| C9—N1—C6—C5 | −0.41 (16) | C14—C15—C18—O2 | −0.05 (19) |
| C9—N1—C6—C1 | 179.89 (11) | C14—C15—C18—C19 | 179.31 (13) |
| C9—C8—C7—C5 | 0.49 (17) | C7—C5—C4—C3 | −179.48 (12) |
| C16—C11—C12—C17 | −177.99 (11) | C5—C6—C1—C2 | −1.07 (19) |
| C16—C11—C12—C13 | 0.99 (17) | C5—C4—C3—C2 | −1.0 (2) |
| C16—C15—C14—C13 | 0.59 (18) | C18—C15—C14—C13 | −177.99 (11) |
| C16—C15—C18—O2 | −178.60 (12) | C1—C6—C5—C7 | −179.50 (11) |
| C16—C15—C18—C19 | 0.76 (19) | C1—C6—C5—C4 | 0.67 (17) |
| C11—N2—C10—O1 | 0.6 (2) | C4—C3—C2—C1 | 0.6 (2) |
| C11—N2—C10—C9 | 179.74 (10) |
(I) N-(5-Acetyl-2-methylphenyl)quinoline-2-carboxamide . Hydrogen-bond geometry (Å, º)
| D—H···A | D—H | H···A | D···A | D—H···A |
| N2—H2···N1 | 0.86 | 2.15 | 2.619 (2) | 114 |
| C17—H17···O1i | 0.96 | 2.49 | 3.424 (2) | 164 |
Symmetry code: (i) −x+2, y+1/2, −z+1/2.
(II) N-(5-Acetyl-2-bromophenyl)quinoline-2-carboxamide . Crystal data
| C18H13BrN2O2 | Z = 2 |
| Mr = 369.21 | F(000) = 372 |
| Triclinic, P1 | Dx = 1.642 Mg m−3 |
| a = 4.29848 (12) Å | Cu Kα radiation, λ = 1.54184 Å |
| b = 11.6353 (3) Å | Cell parameters from 10806 reflections |
| c = 15.5888 (4) Å | θ = 3.9–73.8° |
| α = 103.788 (2)° | µ = 3.85 mm−1 |
| β = 95.515 (2)° | T = 123 K |
| γ = 96.195 (2)° | Plank, clear colourless |
| V = 746.76 (3) Å3 | 0.65 × 0.10 × 0.06 mm |
(II) N-(5-Acetyl-2-bromophenyl)quinoline-2-carboxamide . Data collection
| Agilent TitanS2 GV1000 diffractometer | 2966 independent reflections |
| Radiation source: gradient vaccum rotating-anode X-ray tube, GV1000 (Cu) X-ray Source | 2870 reflections with I > 2σ(I) |
| Mirror monochromator | Rint = 0.033 |
| Detector resolution: 4.1818 pixels mm-1 | θmax = 73.7°, θmin = 2.9° |
| ω scans | h = −5→5 |
| Absorption correction: gaussian [CrysAlis PRO (Rigaku OD, 2015), based on expressions derived by Clark & Reid (1995)] | k = −13→14 |
| Tmin = 0.540, Tmax = 0.900 | l = −19→19 |
| 12899 measured reflections |
(II) N-(5-Acetyl-2-bromophenyl)quinoline-2-carboxamide . Refinement
| Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
| Least-squares matrix: full | H-atom parameters constrained |
| R[F2 > 2σ(F2)] = 0.024 | w = 1/[σ2(Fo2) + (0.039P)2 + 0.3702P] where P = (Fo2 + 2Fc2)/3 |
| wR(F2) = 0.065 | (Δ/σ)max = 0.001 |
| S = 1.05 | Δρmax = 0.48 e Å−3 |
| 2966 reflections | Δρmin = −0.65 e Å−3 |
| 210 parameters | Extinction correction: SHELXL2014 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| 0 restraints | Extinction coefficient: 0.0018 (3) |
(II) N-(5-Acetyl-2-bromophenyl)quinoline-2-carboxamide . Special details
| Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
(II) N-(5-Acetyl-2-bromophenyl)quinoline-2-carboxamide . Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| Br1 | 0.61589 (4) | 0.18439 (2) | 0.04683 (2) | 0.02135 (9) | |
| O1 | 0.5793 (3) | 0.36128 (11) | 0.39598 (8) | 0.0221 (3) | |
| O2 | 1.3517 (3) | −0.04850 (12) | 0.36241 (9) | 0.0289 (3) | |
| N2 | 0.5689 (3) | 0.29917 (12) | 0.24400 (9) | 0.0152 (3) | |
| H2 | 0.4949 | 0.3149 | 0.1955 | 0.018* | |
| N1 | 0.2021 (3) | 0.45877 (12) | 0.22055 (9) | 0.0155 (3) | |
| C11 | 0.7457 (4) | 0.20417 (15) | 0.23433 (11) | 0.0144 (3) | |
| C1 | 0.4988 (4) | 0.37012 (15) | 0.32082 (11) | 0.0161 (3) | |
| C6 | 0.0260 (4) | 0.54368 (15) | 0.20390 (11) | 0.0159 (3) | |
| C15 | 1.0588 (4) | 0.07376 (15) | 0.29489 (11) | 0.0161 (3) | |
| C12 | 0.7872 (4) | 0.13977 (15) | 0.14896 (11) | 0.0161 (3) | |
| C2 | 0.3045 (4) | 0.46475 (15) | 0.30427 (11) | 0.0156 (3) | |
| C16 | 0.8882 (4) | 0.16983 (15) | 0.30694 (11) | 0.0158 (3) | |
| H16 | 0.8683 | 0.2121 | 0.3644 | 0.019* | |
| C13 | 0.9537 (4) | 0.04208 (16) | 0.13641 (11) | 0.0185 (3) | |
| H13 | 0.9742 | −0.0006 | 0.0791 | 0.022* | |
| C3 | 0.2451 (4) | 0.55339 (16) | 0.37799 (11) | 0.0202 (4) | |
| H3 | 0.3202 | 0.5528 | 0.4358 | 0.024* | |
| C14 | 1.0880 (4) | 0.00874 (16) | 0.20912 (11) | 0.0183 (3) | |
| H14 | 1.1978 | −0.0569 | 0.2010 | 0.022* | |
| C18 | 1.2121 (4) | 0.11879 (17) | 0.46469 (11) | 0.0219 (4) | |
| H18A | 0.9983 | 0.1174 | 0.4778 | 0.033* | |
| H18B | 1.2985 | 0.1991 | 0.4666 | 0.033* | |
| H18C | 1.3353 | 0.0903 | 0.5080 | 0.033* | |
| C17 | 1.2189 (4) | 0.03975 (16) | 0.37334 (11) | 0.0187 (3) | |
| C7 | −0.0919 (4) | 0.53725 (16) | 0.11481 (11) | 0.0190 (3) | |
| H7 | −0.0509 | 0.4752 | 0.0692 | 0.023* | |
| C8 | −0.2654 (4) | 0.62145 (17) | 0.09514 (12) | 0.0231 (4) | |
| H8 | −0.3398 | 0.6169 | 0.0362 | 0.028* | |
| C9 | −0.3322 (4) | 0.71549 (17) | 0.16407 (13) | 0.0241 (4) | |
| H9 | −0.4509 | 0.7723 | 0.1501 | 0.029* | |
| C4 | 0.0744 (4) | 0.63973 (16) | 0.36164 (12) | 0.0221 (4) | |
| H4 | 0.0344 | 0.7000 | 0.4087 | 0.026* | |
| C10 | −0.2242 (4) | 0.72361 (16) | 0.25081 (13) | 0.0220 (4) | |
| H10 | −0.2703 | 0.7858 | 0.2955 | 0.026* | |
| C5 | −0.0422 (4) | 0.63791 (15) | 0.27334 (12) | 0.0179 (3) |
(II) N-(5-Acetyl-2-bromophenyl)quinoline-2-carboxamide . Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Br1 | 0.03126 (13) | 0.02289 (13) | 0.01153 (11) | 0.00980 (8) | 0.00226 (7) | 0.00496 (8) |
| O1 | 0.0320 (7) | 0.0228 (7) | 0.0123 (6) | 0.0102 (5) | 0.0028 (5) | 0.0033 (5) |
| O2 | 0.0414 (8) | 0.0268 (7) | 0.0214 (6) | 0.0190 (6) | 0.0013 (6) | 0.0062 (5) |
| N2 | 0.0197 (7) | 0.0159 (7) | 0.0116 (6) | 0.0069 (5) | 0.0031 (5) | 0.0042 (5) |
| N1 | 0.0181 (6) | 0.0141 (7) | 0.0149 (6) | 0.0026 (5) | 0.0049 (5) | 0.0034 (5) |
| C11 | 0.0159 (7) | 0.0133 (8) | 0.0145 (7) | 0.0019 (6) | 0.0036 (6) | 0.0039 (6) |
| C1 | 0.0172 (7) | 0.0155 (8) | 0.0155 (8) | 0.0016 (6) | 0.0039 (6) | 0.0032 (6) |
| C6 | 0.0162 (7) | 0.0138 (8) | 0.0189 (8) | 0.0031 (6) | 0.0063 (6) | 0.0046 (6) |
| C15 | 0.0171 (7) | 0.0164 (8) | 0.0155 (8) | 0.0019 (6) | 0.0027 (6) | 0.0053 (6) |
| C12 | 0.0194 (8) | 0.0181 (8) | 0.0113 (7) | 0.0022 (6) | 0.0018 (6) | 0.0049 (6) |
| C2 | 0.0179 (7) | 0.0138 (8) | 0.0156 (8) | 0.0026 (6) | 0.0056 (6) | 0.0029 (6) |
| C16 | 0.0185 (7) | 0.0166 (8) | 0.0126 (7) | 0.0028 (6) | 0.0038 (6) | 0.0036 (6) |
| C13 | 0.0238 (8) | 0.0173 (9) | 0.0138 (8) | 0.0047 (7) | 0.0050 (6) | 0.0007 (6) |
| C3 | 0.0250 (8) | 0.0211 (9) | 0.0138 (8) | 0.0044 (7) | 0.0041 (6) | 0.0017 (7) |
| C14 | 0.0212 (8) | 0.0148 (8) | 0.0196 (8) | 0.0054 (6) | 0.0044 (7) | 0.0033 (7) |
| C18 | 0.0300 (9) | 0.0223 (9) | 0.0156 (8) | 0.0090 (7) | 0.0026 (7) | 0.0070 (7) |
| C17 | 0.0211 (8) | 0.0196 (9) | 0.0177 (8) | 0.0052 (7) | 0.0040 (6) | 0.0074 (7) |
| C7 | 0.0234 (8) | 0.0170 (9) | 0.0176 (8) | 0.0059 (7) | 0.0055 (7) | 0.0038 (7) |
| C8 | 0.0261 (9) | 0.0232 (10) | 0.0229 (9) | 0.0069 (7) | 0.0028 (7) | 0.0098 (7) |
| C9 | 0.0238 (9) | 0.0181 (9) | 0.0336 (10) | 0.0086 (7) | 0.0051 (7) | 0.0096 (8) |
| C4 | 0.0270 (9) | 0.0180 (9) | 0.0191 (8) | 0.0062 (7) | 0.0068 (7) | −0.0023 (7) |
| C10 | 0.0235 (8) | 0.0135 (8) | 0.0291 (9) | 0.0060 (7) | 0.0085 (7) | 0.0015 (7) |
| C5 | 0.0183 (8) | 0.0139 (8) | 0.0215 (8) | 0.0027 (6) | 0.0071 (6) | 0.0026 (7) |
(II) N-(5-Acetyl-2-bromophenyl)quinoline-2-carboxamide . Geometric parameters (Å, º)
| Br1—C12 | 1.8968 (16) | C13—H13 | 0.9300 |
| O1—C1 | 1.221 (2) | C13—C14 | 1.379 (2) |
| O2—C17 | 1.213 (2) | C3—H3 | 0.9300 |
| N2—H2 | 0.8600 | C3—C4 | 1.363 (3) |
| N2—C11 | 1.395 (2) | C14—H14 | 0.9300 |
| N2—C1 | 1.363 (2) | C18—H18A | 0.9600 |
| N1—C6 | 1.365 (2) | C18—H18B | 0.9600 |
| N1—C2 | 1.320 (2) | C18—H18C | 0.9600 |
| C11—C12 | 1.401 (2) | C18—C17 | 1.505 (2) |
| C11—C16 | 1.397 (2) | C7—H7 | 0.9300 |
| C1—C2 | 1.506 (2) | C7—C8 | 1.366 (3) |
| C6—C7 | 1.413 (2) | C8—H8 | 0.9300 |
| C6—C5 | 1.423 (2) | C8—C9 | 1.415 (3) |
| C15—C16 | 1.388 (2) | C9—H9 | 0.9300 |
| C15—C14 | 1.395 (2) | C9—C10 | 1.365 (3) |
| C15—C17 | 1.501 (2) | C4—H4 | 0.9300 |
| C12—C13 | 1.392 (2) | C4—C5 | 1.413 (3) |
| C2—C3 | 1.414 (2) | C10—H10 | 0.9300 |
| C16—H16 | 0.9300 | C10—C5 | 1.419 (3) |
| C11—N2—H2 | 116.0 | C15—C14—H14 | 120.1 |
| C1—N2—H2 | 116.0 | C13—C14—C15 | 119.79 (16) |
| C1—N2—C11 | 128.05 (14) | C13—C14—H14 | 120.1 |
| C2—N1—C6 | 117.86 (14) | H18A—C18—H18B | 109.5 |
| N2—C11—C12 | 119.73 (14) | H18A—C18—H18C | 109.5 |
| N2—C11—C16 | 122.69 (14) | H18B—C18—H18C | 109.5 |
| C16—C11—C12 | 117.58 (15) | C17—C18—H18A | 109.5 |
| O1—C1—N2 | 125.78 (16) | C17—C18—H18B | 109.5 |
| O1—C1—C2 | 121.70 (15) | C17—C18—H18C | 109.5 |
| N2—C1—C2 | 112.53 (14) | O2—C17—C15 | 120.30 (16) |
| N1—C6—C7 | 118.71 (15) | O2—C17—C18 | 121.59 (16) |
| N1—C6—C5 | 122.01 (15) | C15—C17—C18 | 118.10 (15) |
| C7—C6—C5 | 119.28 (16) | C6—C7—H7 | 119.7 |
| C16—C15—C14 | 120.08 (15) | C8—C7—C6 | 120.57 (16) |
| C16—C15—C17 | 120.76 (15) | C8—C7—H7 | 119.7 |
| C14—C15—C17 | 119.14 (15) | C7—C8—H8 | 119.9 |
| C11—C12—Br1 | 120.33 (13) | C7—C8—C9 | 120.21 (17) |
| C13—C12—Br1 | 118.19 (12) | C9—C8—H8 | 119.9 |
| C13—C12—C11 | 121.48 (15) | C8—C9—H9 | 119.7 |
| N1—C2—C1 | 116.81 (14) | C10—C9—C8 | 120.64 (17) |
| N1—C2—C3 | 124.47 (16) | C10—C9—H9 | 119.7 |
| C3—C2—C1 | 118.73 (15) | C3—C4—H4 | 119.9 |
| C11—C16—H16 | 119.4 | C3—C4—C5 | 120.19 (16) |
| C15—C16—C11 | 121.17 (15) | C5—C4—H4 | 119.9 |
| C15—C16—H16 | 119.4 | C9—C10—H10 | 119.8 |
| C12—C13—H13 | 120.1 | C9—C10—C5 | 120.48 (16) |
| C14—C13—C12 | 119.84 (15) | C5—C10—H10 | 119.8 |
| C14—C13—H13 | 120.1 | C4—C5—C6 | 117.53 (16) |
| C2—C3—H3 | 121.0 | C4—C5—C10 | 123.66 (16) |
| C4—C3—C2 | 117.93 (16) | C10—C5—C6 | 118.80 (16) |
| C4—C3—H3 | 121.0 | ||
| Br1—C12—C13—C14 | 178.46 (13) | C2—N1—C6—C7 | −178.60 (15) |
| O1—C1—C2—N1 | −173.05 (15) | C2—N1—C6—C5 | 1.4 (2) |
| O1—C1—C2—C3 | 7.2 (2) | C2—C3—C4—C5 | 1.1 (3) |
| N2—C11—C12—Br1 | 2.1 (2) | C16—C11—C12—Br1 | −177.52 (12) |
| N2—C11—C12—C13 | −177.97 (15) | C16—C11—C12—C13 | 2.5 (2) |
| N2—C11—C16—C15 | 179.08 (15) | C16—C15—C14—C13 | 1.7 (2) |
| N2—C1—C2—N1 | 7.0 (2) | C16—C15—C17—O2 | 175.63 (17) |
| N2—C1—C2—C3 | −172.76 (15) | C16—C15—C17—C18 | −5.1 (2) |
| N1—C6—C7—C8 | −179.06 (16) | C3—C4—C5—C6 | 0.0 (3) |
| N1—C6—C5—C4 | −1.3 (2) | C3—C4—C5—C10 | 179.32 (17) |
| N1—C6—C5—C10 | 179.38 (15) | C14—C15—C16—C11 | −0.7 (2) |
| N1—C2—C3—C4 | −1.0 (3) | C14—C15—C17—O2 | −5.5 (2) |
| C11—N2—C1—O1 | −0.7 (3) | C14—C15—C17—C18 | 173.78 (16) |
| C11—N2—C1—C2 | 179.29 (14) | C17—C15—C16—C11 | 178.22 (14) |
| C11—C12—C13—C14 | −1.5 (3) | C17—C15—C14—C13 | −177.24 (15) |
| C1—N2—C11—C12 | 178.73 (15) | C7—C6—C5—C4 | 178.70 (15) |
| C1—N2—C11—C16 | −1.7 (3) | C7—C6—C5—C10 | −0.7 (2) |
| C1—C2—C3—C4 | 178.68 (15) | C7—C8—C9—C10 | 0.1 (3) |
| C6—N1—C2—C1 | −179.91 (14) | C8—C9—C10—C5 | 0.2 (3) |
| C6—N1—C2—C3 | −0.2 (2) | C9—C10—C5—C6 | 0.1 (3) |
| C6—C7—C8—C9 | −0.7 (3) | C9—C10—C5—C4 | −179.22 (17) |
| C12—C11—C16—C15 | −1.4 (2) | C5—C6—C7—C8 | 1.0 (3) |
| C12—C13—C14—C15 | −0.6 (3) |
(II) N-(5-Acetyl-2-bromophenyl)quinoline-2-carboxamide . Hydrogen-bond geometry (Å, º)
| D—H···A | D—H | H···A | D···A | D—H···A |
| N2—H2···N1 | 0.86 | 2.19 | 2.629 (2) | 112 |
| C3—H3···O1i | 0.93 | 2.55 | 3.410 (2) | 154 |
| C18—H18···O2ii | 0.96 | 2.49 | 3.444 (2) | 171 |
| N2—H2···Br1 | 0.86 | 2.58 | 3.081 (1) | 118 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+3, −y, −z+1.
(III) N-(5-Acetyl-2-ethynylphenyl)quinoline-2-carboxamide . Crystal data
| C20H14N2O2 | Z = 2 |
| Mr = 314.33 | F(000) = 328 |
| Triclinic, P1 | Dx = 1.356 Mg m−3 |
| a = 7.3075 (6) Å | Mo Kα radiation, λ = 0.71073 Å |
| b = 8.2605 (4) Å | Cell parameters from 5519 reflections |
| c = 13.8196 (9) Å | θ = 3.1–32.0° |
| α = 92.734 (5)° | µ = 0.09 mm−1 |
| β = 100.608 (6)° | T = 123 K |
| γ = 108.989 (6)° | Block, colourless |
| V = 770.11 (10) Å3 | 0.19 × 0.08 × 0.05 mm |
(III) N-(5-Acetyl-2-ethynylphenyl)quinoline-2-carboxamide . Data collection
| Agilent SuperNova Single source at offset, Eos diffractometer | 5173 independent reflections |
| Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source | 3687 reflections with I > 2σ(I) |
| Mirror monochromator | Rint = 0.060 |
| Detector resolution: 7.9851 pixels mm-1 | θmax = 32.3°, θmin = 3.0° |
| ω scans | h = −10→10 |
| Absorption correction: analytical [CrysAlis PRO (Rigaku OD, 2015), based on expressions derived by Clark & Reid (1995)] | k = −12→12 |
| Tmin = 0.987, Tmax = 0.996 | l = −20→20 |
| 20693 measured reflections |
(III) N-(5-Acetyl-2-ethynylphenyl)quinoline-2-carboxamide . Refinement
| Refinement on F2 | 0 restraints |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.056 | H-atom parameters constrained |
| wR(F2) = 0.151 | w = 1/[σ2(Fo2) + (0.0577P)2 + 0.282P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.04 | (Δ/σ)max < 0.001 |
| 5173 reflections | Δρmax = 0.42 e Å−3 |
| 218 parameters | Δρmin = −0.26 e Å−3 |
(III) N-(5-Acetyl-2-ethynylphenyl)quinoline-2-carboxamide . Special details
| Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
(III) N-(5-Acetyl-2-ethynylphenyl)quinoline-2-carboxamide . Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| O2 | 0.81853 (17) | 0.81639 (13) | 0.58241 (8) | 0.0298 (3) | |
| O1 | 0.69300 (18) | 0.80001 (15) | 1.00770 (8) | 0.0344 (3) | |
| N1 | 0.73126 (17) | 0.52751 (15) | 0.59954 (8) | 0.0204 (2) | |
| H1 | 0.7132 | 0.4296 | 0.5678 | 0.025* | |
| N2 | 0.76917 (16) | 0.45956 (15) | 0.41516 (8) | 0.0204 (2) | |
| C11 | 0.7866 (2) | 0.66691 (18) | 0.54929 (10) | 0.0211 (3) | |
| C16 | 0.78375 (19) | 0.41914 (18) | 0.32020 (10) | 0.0205 (3) | |
| C8 | 0.6340 (2) | 0.49494 (18) | 0.88964 (10) | 0.0225 (3) | |
| H8 | 0.6117 | 0.4859 | 0.9536 | 0.027* | |
| C3 | 0.69438 (19) | 0.65661 (18) | 0.85563 (9) | 0.0199 (3) | |
| C9 | 0.6242 (2) | 0.20816 (18) | 0.66981 (10) | 0.0235 (3) | |
| C4 | 0.72565 (19) | 0.67055 (17) | 0.75912 (9) | 0.0201 (3) | |
| H4 | 0.7637 | 0.7782 | 0.7364 | 0.024* | |
| C6 | 0.64210 (19) | 0.36039 (17) | 0.73190 (9) | 0.0200 (3) | |
| C5 | 0.69995 (19) | 0.52316 (17) | 0.69665 (9) | 0.0190 (3) | |
| C15 | 0.8349 (2) | 0.54711 (19) | 0.25516 (10) | 0.0226 (3) | |
| C12 | 0.80629 (19) | 0.62324 (17) | 0.44536 (9) | 0.0198 (3) | |
| C2 | 0.7259 (2) | 0.81339 (19) | 0.92427 (10) | 0.0238 (3) | |
| C13 | 0.8613 (2) | 0.75994 (18) | 0.38704 (10) | 0.0235 (3) | |
| H13 | 0.8881 | 0.8734 | 0.4126 | 0.028* | |
| C7 | 0.6074 (2) | 0.34872 (18) | 0.82831 (10) | 0.0227 (3) | |
| H7 | 0.5661 | 0.2413 | 0.8511 | 0.027* | |
| C17 | 0.7457 (2) | 0.24391 (19) | 0.28605 (11) | 0.0264 (3) | |
| H17 | 0.7138 | 0.1593 | 0.3282 | 0.032* | |
| C10 | 0.6224 (2) | 0.0885 (2) | 0.61968 (12) | 0.0305 (3) | |
| H10 | 0.6210 | −0.0063 | 0.5800 | 0.037* | |
| C14 | 0.8738 (2) | 0.72010 (19) | 0.29172 (10) | 0.0249 (3) | |
| H14 | 0.9079 | 0.8069 | 0.2511 | 0.030* | |
| C20 | 0.8445 (2) | 0.4964 (2) | 0.15714 (10) | 0.0283 (3) | |
| H20 | 0.8776 | 0.5790 | 0.1140 | 0.034* | |
| C18 | 0.7560 (2) | 0.2000 (2) | 0.19069 (12) | 0.0309 (3) | |
| H18 | 0.7302 | 0.0851 | 0.1685 | 0.037* | |
| C19 | 0.8051 (2) | 0.3267 (2) | 0.12586 (11) | 0.0315 (3) | |
| H19 | 0.8108 | 0.2945 | 0.0614 | 0.038* | |
| C1 | 0.8052 (3) | 0.9875 (2) | 0.89000 (11) | 0.0326 (4) | |
| H1A | 0.8080 | 1.0748 | 0.9392 | 0.049* | |
| H1B | 0.7214 | 0.9926 | 0.8288 | 0.049* | |
| H1C | 0.9369 | 1.0066 | 0.8801 | 0.049* |
(III) N-(5-Acetyl-2-ethynylphenyl)quinoline-2-carboxamide . Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O2 | 0.0459 (7) | 0.0218 (5) | 0.0232 (5) | 0.0113 (5) | 0.0114 (5) | 0.0015 (4) |
| O1 | 0.0440 (7) | 0.0339 (6) | 0.0211 (5) | 0.0056 (5) | 0.0126 (5) | −0.0035 (4) |
| N1 | 0.0256 (6) | 0.0189 (5) | 0.0162 (5) | 0.0063 (4) | 0.0057 (4) | 0.0002 (4) |
| N2 | 0.0197 (5) | 0.0215 (5) | 0.0187 (5) | 0.0054 (4) | 0.0043 (4) | 0.0001 (4) |
| C11 | 0.0238 (6) | 0.0227 (6) | 0.0167 (6) | 0.0079 (5) | 0.0042 (5) | 0.0012 (5) |
| C16 | 0.0180 (6) | 0.0240 (7) | 0.0180 (6) | 0.0060 (5) | 0.0034 (5) | −0.0014 (5) |
| C8 | 0.0225 (6) | 0.0279 (7) | 0.0173 (6) | 0.0077 (5) | 0.0062 (5) | 0.0034 (5) |
| C3 | 0.0189 (6) | 0.0236 (6) | 0.0161 (5) | 0.0064 (5) | 0.0032 (5) | −0.0011 (5) |
| C9 | 0.0234 (7) | 0.0252 (7) | 0.0224 (6) | 0.0072 (5) | 0.0071 (5) | 0.0070 (5) |
| C4 | 0.0207 (6) | 0.0211 (6) | 0.0173 (6) | 0.0055 (5) | 0.0039 (5) | 0.0012 (5) |
| C6 | 0.0195 (6) | 0.0214 (6) | 0.0186 (6) | 0.0061 (5) | 0.0041 (5) | 0.0015 (5) |
| C5 | 0.0182 (6) | 0.0231 (6) | 0.0158 (5) | 0.0067 (5) | 0.0047 (4) | 0.0026 (5) |
| C15 | 0.0192 (6) | 0.0308 (7) | 0.0164 (6) | 0.0072 (5) | 0.0031 (5) | 0.0014 (5) |
| C12 | 0.0201 (6) | 0.0217 (6) | 0.0165 (5) | 0.0058 (5) | 0.0036 (5) | 0.0006 (5) |
| C2 | 0.0241 (7) | 0.0273 (7) | 0.0184 (6) | 0.0083 (6) | 0.0027 (5) | −0.0022 (5) |
| C13 | 0.0280 (7) | 0.0209 (6) | 0.0196 (6) | 0.0057 (5) | 0.0045 (5) | 0.0016 (5) |
| C7 | 0.0238 (7) | 0.0225 (6) | 0.0219 (6) | 0.0066 (5) | 0.0071 (5) | 0.0044 (5) |
| C17 | 0.0250 (7) | 0.0247 (7) | 0.0278 (7) | 0.0068 (6) | 0.0061 (6) | −0.0023 (5) |
| C10 | 0.0358 (8) | 0.0276 (7) | 0.0272 (7) | 0.0098 (6) | 0.0065 (6) | 0.0020 (6) |
| C14 | 0.0266 (7) | 0.0266 (7) | 0.0202 (6) | 0.0059 (6) | 0.0066 (5) | 0.0063 (5) |
| C20 | 0.0256 (7) | 0.0418 (9) | 0.0177 (6) | 0.0119 (6) | 0.0048 (5) | 0.0020 (6) |
| C18 | 0.0285 (8) | 0.0317 (8) | 0.0302 (8) | 0.0103 (6) | 0.0038 (6) | −0.0090 (6) |
| C19 | 0.0295 (8) | 0.0453 (9) | 0.0197 (6) | 0.0152 (7) | 0.0037 (6) | −0.0059 (6) |
| C1 | 0.0483 (10) | 0.0241 (7) | 0.0223 (7) | 0.0107 (7) | 0.0044 (6) | −0.0023 (6) |
(III) N-(5-Acetyl-2-ethynylphenyl)quinoline-2-carboxamide . Geometric parameters (Å, º)
| O2—C11 | 1.2279 (17) | C6—C7 | 1.4033 (18) |
| O1—C2 | 1.2231 (17) | C15—C14 | 1.411 (2) |
| N1—H1 | 0.8600 | C15—C20 | 1.4195 (19) |
| N1—C11 | 1.3595 (18) | C12—C13 | 1.4130 (19) |
| N1—C5 | 1.4025 (16) | C2—C1 | 1.501 (2) |
| N2—C16 | 1.3704 (17) | C13—H13 | 0.9300 |
| N2—C12 | 1.3197 (17) | C13—C14 | 1.3692 (19) |
| C11—C12 | 1.5082 (18) | C7—H7 | 0.9300 |
| C16—C15 | 1.422 (2) | C17—H17 | 0.9300 |
| C16—C17 | 1.421 (2) | C17—C18 | 1.372 (2) |
| C8—H8 | 0.9300 | C10—H10 | 0.9300 |
| C8—C3 | 1.397 (2) | C14—H14 | 0.9300 |
| C8—C7 | 1.3799 (19) | C20—H20 | 0.9300 |
| C3—C4 | 1.3979 (18) | C20—C19 | 1.367 (2) |
| C3—C2 | 1.4962 (19) | C18—H18 | 0.9300 |
| C9—C6 | 1.4435 (19) | C18—C19 | 1.411 (2) |
| C9—C10 | 1.175 (2) | C19—H19 | 0.9300 |
| C4—H4 | 0.9300 | C1—H1A | 0.9600 |
| C4—C5 | 1.3979 (18) | C1—H1B | 0.9600 |
| C6—C5 | 1.4115 (18) | C1—H1C | 0.9600 |
| C11—N1—H1 | 115.9 | O1—C2—C3 | 120.60 (13) |
| C11—N1—C5 | 128.21 (12) | O1—C2—C1 | 120.68 (13) |
| C5—N1—H1 | 115.9 | C3—C2—C1 | 118.69 (12) |
| C12—N2—C16 | 117.64 (12) | C12—C13—H13 | 121.0 |
| O2—C11—N1 | 125.11 (12) | C14—C13—C12 | 117.90 (13) |
| O2—C11—C12 | 121.14 (12) | C14—C13—H13 | 121.0 |
| N1—C11—C12 | 113.75 (11) | C8—C7—C6 | 120.69 (13) |
| N2—C16—C15 | 121.91 (12) | C8—C7—H7 | 119.7 |
| N2—C16—C17 | 118.75 (13) | C6—C7—H7 | 119.7 |
| C17—C16—C15 | 119.33 (12) | C16—C17—H17 | 120.1 |
| C3—C8—H8 | 120.0 | C18—C17—C16 | 119.78 (14) |
| C7—C8—H8 | 120.0 | C18—C17—H17 | 120.1 |
| C7—C8—C3 | 119.98 (12) | C9—C10—H10 | 180.0 |
| C8—C3—C4 | 120.17 (12) | C15—C14—H14 | 120.0 |
| C8—C3—C2 | 118.92 (12) | C13—C14—C15 | 119.92 (13) |
| C4—C3—C2 | 120.92 (12) | C13—C14—H14 | 120.0 |
| C10—C9—C6 | 175.76 (16) | C15—C20—H20 | 119.8 |
| C3—C4—H4 | 119.9 | C19—C20—C15 | 120.33 (15) |
| C3—C4—C5 | 120.21 (12) | C19—C20—H20 | 119.8 |
| C5—C4—H4 | 119.9 | C17—C18—H18 | 119.5 |
| C5—C6—C9 | 119.94 (12) | C17—C18—C19 | 120.92 (14) |
| C7—C6—C9 | 120.52 (12) | C19—C18—H18 | 119.5 |
| C7—C6—C5 | 119.51 (12) | C20—C19—C18 | 120.49 (14) |
| N1—C5—C6 | 117.23 (12) | C20—C19—H19 | 119.8 |
| C4—C5—N1 | 123.36 (12) | C18—C19—H19 | 119.8 |
| C4—C5—C6 | 119.41 (12) | C2—C1—H1A | 109.5 |
| C14—C15—C16 | 117.90 (12) | C2—C1—H1B | 109.5 |
| C14—C15—C20 | 122.96 (14) | C2—C1—H1C | 109.5 |
| C20—C15—C16 | 119.14 (13) | H1A—C1—H1B | 109.5 |
| N2—C12—C11 | 117.50 (12) | H1A—C1—H1C | 109.5 |
| N2—C12—C13 | 124.71 (12) | H1B—C1—H1C | 109.5 |
| C13—C12—C11 | 117.78 (12) | ||
| O2—C11—C12—N2 | −179.91 (13) | C9—C6—C5—C4 | −177.04 (12) |
| O2—C11—C12—C13 | −0.5 (2) | C9—C6—C7—C8 | 176.73 (13) |
| N1—C11—C12—N2 | −0.07 (18) | C4—C3—C2—O1 | 177.96 (13) |
| N1—C11—C12—C13 | 179.34 (12) | C4—C3—C2—C1 | −4.1 (2) |
| N2—C16—C15—C14 | 0.9 (2) | C5—N1—C11—O2 | −0.2 (2) |
| N2—C16—C15—C20 | −179.00 (12) | C5—N1—C11—C12 | 180.00 (12) |
| N2—C16—C17—C18 | 178.87 (13) | C5—C6—C7—C8 | −1.6 (2) |
| N2—C12—C13—C14 | 1.2 (2) | C15—C16—C17—C18 | −0.9 (2) |
| C11—N1—C5—C4 | −1.0 (2) | C15—C20—C19—C18 | −0.5 (2) |
| C11—N1—C5—C6 | 179.84 (13) | C12—N2—C16—C15 | −0.63 (19) |
| C11—C12—C13—C14 | −178.19 (12) | C12—N2—C16—C17 | 179.63 (12) |
| C16—N2—C12—C11 | 178.94 (11) | C12—C13—C14—C15 | −0.8 (2) |
| C16—N2—C12—C13 | −0.4 (2) | C2—C3—C4—C5 | 178.53 (12) |
| C16—C15—C14—C13 | −0.1 (2) | C7—C8—C3—C4 | 0.8 (2) |
| C16—C15—C20—C19 | −0.1 (2) | C7—C8—C3—C2 | −178.82 (13) |
| C16—C17—C18—C19 | 0.4 (2) | C7—C6—C5—N1 | −179.53 (12) |
| C8—C3—C4—C5 | −1.1 (2) | C7—C6—C5—C4 | 1.28 (19) |
| C8—C3—C2—O1 | −2.4 (2) | C17—C16—C15—C14 | −179.36 (13) |
| C8—C3—C2—C1 | 175.51 (13) | C17—C16—C15—C20 | 0.7 (2) |
| C3—C8—C7—C6 | 0.5 (2) | C17—C18—C19—C20 | 0.3 (2) |
| C3—C4—C5—N1 | −179.10 (12) | C14—C15—C20—C19 | −179.97 (14) |
| C3—C4—C5—C6 | 0.04 (19) | C20—C15—C14—C13 | 179.78 (13) |
| C9—C6—C5—N1 | 2.14 (18) |
(III) N-(5-Acetyl-2-ethynylphenyl)quinoline-2-carboxamide . Hydrogen-bond geometry (Å, º)
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1···N2 | 0.86 | 2.23 | 2.666 (2) | 111 |
| C10—H10···O2i | 0.93 | 2.36 | 3.103 (2) | 136 |
Symmetry code: (i) x, y−1, z.
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) I, II, III. DOI: 10.1107/S2056989017006272/lh5839sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989017006272/lh5839Isup2.hkl
Structure factors: contains datablock(s) II. DOI: 10.1107/S2056989017006272/lh5839IIsup3.hkl
Structure factors: contains datablock(s) III. DOI: 10.1107/S2056989017006272/lh5839IIIsup4.hkl
Supporting information file. DOI: 10.1107/S2056989017006272/lh5839Isup5.cml
Supporting information file. DOI: 10.1107/S2056989017006272/lh5839IIsup6.cml
Supporting information file. DOI: 10.1107/S2056989017006272/lh5839IIIsup7.cml
Additional supporting information: crystallographic information; 3D view; checkCIF report