Skip to main content
NCBI home page
Acta Crystallographica Section E: Crystallographic Communications logoLink to Acta Crystallographica Section E: Crystallographic Communications
. 2021 Mar 5;77(Pt 4):351–355. doi: 10.1107/S2056989021002140

Crystal structures of 1-(4-chloro­phen­yl)-4-(4-methyl­phen­yl)-2,5-dioxo-1,2,5,6,7,8-hexa­hydro­quinoline-3-carb­oxy­lic acid and 4-(4-meth­oxy­phen­yl)-1-(4-methyl­phen­yl)-2,5-dioxo-1,2,5,6,7,8-hexa­hydro­quinoline-3-carbo­nitrile

Omyma A Abd Allah a, Manpreet Kaur b, Mehmet Akkurt c, Shaaban K Mohamed d,e,*, Asmaa H A Tamam a, Sahar M I Elgarhy f, Jerry P Jasinski b
PMCID: PMC8025871  PMID: 33936756

The asymmetric units of compounds I and II both consist of two independent mol­ecules. In the crystal of I, mol­ecules are linked through N—H⋯O hydrogen bonds, forming inversion dimers with Inline graphic(8) ring motifs and with their mol­ecular planes parallel to (020). C—H⋯O inter­actions connect the dimers, forming a three-dimensional network. In the crystal of II, mol­ecules are linked by C—H⋯N, C—H⋯O and C—H⋯π inter­actions, resulting in a three-dimensional network.

Keywords: crystal structure, cyclo­hexene ring, di­hydro­pyridine ring, hexa­hydro­quinoline ring, dimer

Abstract

In the title compounds C23H21ClN2O3 [I, namely 1-(4-chloro­phen­yl)-4-(4-methyl­phen­yl)-3,8-dioxo-1,2,5,6,7,8-hexa­hydro­quine-3-carb­oxy­lic acid] and C24H22N2O3 [II, namely 4-(4-meth­oxy­phen­yl)-1-(4-methyl­phen­yl)-2,5-dioxo-1,2,5,6,7,8-hexa­hydro­quinoline-3-carbo­nitrile], each of the cyclo­hexene and di­hydro­pyridine rings of the 1,2,5,6,7,8-hexa­hydro­quinoline moieties adopts a twisted-boat conformation. The asymmetric units of both compounds I and II consist of two independent mol­ecules (A and B). In II A, three carbon atoms of the cyclo­hexene ring are disordered over two sets of sites in a 0.670 (11):0.330 (11) occupancy ratio. In the crystal of I, mol­ecules are linked through classical N—H⋯O hydrogen bonds, forming inversion dimers with an R 2 2(8) ring motif and with their mol­ecular planes parallel to the crystallographic (020) plane. Non-classical C—H⋯O hydrogen-bonding inter­actions connect the dimers, resulting in a three-dimensional network. In the crystal of II, mol­ecules are linked by C—H⋯N, C—H⋯O and C—H⋯π inter­actions, forming a three-dimensional network.

Chemical context  

Quinoline and its derivatives have for some time attracted the attention of both synthetic and biological chemists as a result of their diverse chemical and pharmacological properties (Kumar et al., 2009 ▸). There are a number of natural products bearing the quinoline skeleton that are used as a medicine or employed as lead mol­ecule for the development of new and potent therapeutics (Venkat Reddy et al., 2009 ▸). Quinoline derivatives fused with various heterocycles have already demonstrated potent anti­cancer activity (Afzal et al., 2015 ▸). In addition, it has been found that various quinoline compounds show anti-tuberculosis (TB) activity (Muscia et al., 2014 ▸), anti-inflammatory activity (Psomas & Kessissoglou, 2013 ▸), anti-convulsant effects (Guo et al., 2009 ▸), and anti-malarial parasite effects (Abdel-Gawad et al., 2005 ▸). Furthermore, quinolones have been proved to be very effective in many anti­microbial and anti­oxidant investigations (Praveen et al., 2010 ▸). In this context, we report herein the crystal structures of two derivatives of hexa­hydro­quinoline.graphic file with name e-77-00351-scheme1.jpg

Structural commentary  

Compound I crystallizes in the ortho­rhom­bic space group Pbca with Z = 16, while compound II crystallizes in the monoclinic space group P21/c with Z = 8. The asymmetric units of both compounds (I and II) each comprise two mol­ecules (A and B). As shown in Figs. 1 ▸ and 2 ▸, the cyclo­hexene (C4–C9) and di­hydro­pyridine (N1/C1–C4/C9) rings of the 1,2,5,6,7,8-hexa­hydro­quinoline moieties (N1/C1–C9) each adopt a twisted-boat conformation. The puckering parameters (Cremer & Pople, 1975 ▸) of the cyclo­hexene rings are Q T = 0.441 (3) Å, θ = 123.3 (3)°, and φ = 1.3 (3)° for I A, Q T = 0.450 (2) Å, θ = 122.0 (3)°, and φ = 4.3 (3)° for I B, Q T = 0.352 (8) Å, θ = 60.7 (11)°, and φ = 188.1 (13)° for II A (major component of the disorder), and Q T = 0.446 (2) Å, θ = 123.5 (3)°, and φ = 355.2 (3)° for II B. The puckering parameters of the di­hydro­pyridine rings are Q T = 0.4929 (18) Å, θ = 64.2 (2)°, and φ = 150.6 (2)° for I A, Q T = 0.4529 (18) Å, θ = 61.1 (2)°, and φ = 139.9 (3)° for I B, Q T = 0.422 (2) Å, θ = 58.9 (3)°, and φ = 138.4 (3)° for II A and Q T = 0.437 (2) Å, θ = 62.5 (3)°, and φ = 142.1 (3)° for II B.

Figure 1.

Figure 1

Open in a new tab

The mol­ecular structure of I with the atom-numbering scheme and with displacement ellipsoids drawn at the 30% probability level.

Figure 2.

Figure 2

Open in a new tab

The mol­ecular structure of II with the atom-numbering scheme and with displacement ellipsoids drawn at the 20% probability level.

Supra­molecular features  

In the crystal of I, two mol­ecules are linked by a pair of inter­molecular N—H⋯O hydrogen bonds with an Inline graphic(8) ring motif (Bernstein et al., 1995 ▸; Table 1 ▸), forming an inversion dimer (Fig. 3 ▸). These assemble into a three-dimensional network via C—H⋯O inter­actions. In the crystal of II, mol­ecules are linked by non-classical C—H⋯O, C—H⋯N and C—H⋯π inter­actions, resulting in a three-dimensional network (Table 2 ▸ and Figs. 4 ▸ and 5 ▸). In the crystals of the two compounds (I and II) π-π-stacking inter­actions are not observed despite the presence of two aromatic rings in every mol­ecule.

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

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N2A—H2A2⋯O2A i 0.88 (2) 2.12 (3) 2.979 (2) 164 (2)
N2B—H2B1⋯O2A ii 0.86 (2) 2.26 (2) 3.055 (2) 154 (2)
N2A—H2A1⋯O3B 0.86 (2) 2.06 (2) 2.865 (2) 156 (2)
N2B—H2B2⋯O3A 0.85 (3) 2.04 (3) 2.847 (2) 159 (2)
C8A—H8AB⋯O2B ii 0.97 2.50 3.392 (2) 153
C6B—H6BB⋯O1B iii 0.97 2.57 3.430 (2) 148
C14A—H14A⋯O1A iv 0.93 2.54 3.393 (3) 153
C17B—H17B⋯O1B v 0.93 2.52 3.424 (3) 164
Open in a new tab

Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x+1, -y+1, -z+1; (iii) x, y-1, z; (iv) -x+{\script{3\over 2}}, y+{\script{1\over 2}}, z; (v) -x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}.

Figure 3.

Figure 3

Open in a new tab

The crystal packing of I viewed down the b axis showing inter­molecular hydrogen bonds as dashed lines.

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

Cg4 and Cg9 are the centroids of the C10A–C15A and C16B–C21B rings, respectively.

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C21A—H21A⋯N2B i 0.95 2.65 3.258 (4) 123
C14B—H14B⋯O3A ii 0.95 2.65 3.417 (3) 139
C3A—H3A⋯O1B 1.00 2.37 3.171 (2) 136
C23B—H23E⋯Cg9iii 0.98 2.93 3.868 (3) 160
C23B—H23F⋯Cg4iv 0.98 2.74 3.710 (3) 169
Open in a new tab

Symmetry codes: (i) -x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}; (ii) x, y-1, z; (iii) -x+2, -y+1, -z+1; (iv) -x+1, -y+1, -z+1.

Figure 4.

Figure 4

Open in a new tab

A view of the C—H⋯π inter­actions in II shown as dashed lines. [Symmetry codes: (a) 1 − x, 1 − y, 1 − z; (b) 2 − x, 1 − y, 1 − z].

Figure 5.

Figure 5

Open in a new tab

The crystal packing of II viewed down the b axis showing the inter­molecular hydrogen bonds as dashed lines.

Database survey  

A search of the Cambridge Structural Database (CSD, Version 5.40, February 2019; Groom et al., 2016 ▸) for the 4-phenyl-2,3,4,6,7,8-hexa­hydro­quinolin-5(1H)-one moiety resulted in six closely related hits, viz. 2-amino-4-(4-chloro­phen­yl)-1-(4-methyl­phen­yl)-5-oxo-1,4,5,6,7,8-hexa­hydro­quin­oline-3-carbo­nitrile (HUYVUU; Mohamed et al., 2015 ▸), methyl-2,7,7-trimethyl-4-(3-nitro­phen­yl)-5-oxo-1,4,5,6,7,8-hexa­hydro­quinoline-3-carboxyl­ate (TEJQII; Morales et al., 1996 ▸), 3-acetyl-2,7,7-trimethyl-4-phenyl-1,4,5,6,7,8-hexa­hydro-5-quinolone (TEJQOO; Morales et al., 1996 ▸), 4-(4-chloro­phen­yl)-8-methyl-2-oxo-1,2,5,6,7,8-hexa­hydro­quinoline-3-carbo­nitrile (AZOWAO; Asiri et al., 2011 ▸), 8-methyl-2-oxo-4-(thio­phen-2-yl)-1,2,5,6,7,8-hexa­hydro­quinoline-3-carbo­nitrile (XECCAL; Asiri et al., 2012 ▸) and ethyl-2,7,7-trimethyl-5-oxo-4-phenyl-1,4,5,6,7,8-hexa­hydro­quinoline-3-carboxyl­ate (XAYVEA; Kurbanova et al., 2012 ▸).

In compounds I and II, the observed bond lengths and bond angles are in good agreement with the reported experimental values as found in the structures of HUYVUU, TEJQII, TEJQOO, AZOWAO, XECCAL and XAYVEA. The metrical parameters are, hence, unremarkable.

The angles between the planes of the two benzene rings in I and II are 52.64 (11)° for I A, 33.78 (12)° for I B, 21.80 (11)° for II A and 19.39 (11)° for II B, respectively. These angles are notably distinct, even for the two independent mol­ecules in each structure. They are all also significantly larger than the value of 11.52 (7)° found in HUYVUU (the only other example with two benzene rings amongst the related structures). Inter­molecular inter­actions can be weaker or stronger based on the presence or absence or difference of functional groups and the mol­ecular environment, depending on the crystal system, which all affect the mol­ecular conformation. The observed difference in the angles between the two benzene rings may be attributed to these factors.

Synthesis and crystallization  

1-(4-Chloro­phen­yl)-4-(4-methyl­phen­yl)-3,8-dioxo-1,2,5,6,7,8-hexa­hydro­quine-3-carboxlic acid, I

A solution of 2-amino-4-(4-chloro­phen­yl)-1-(4-methyl­phen­yl)-5-oxo-1,4,5,6,7,8-hexa­hydro­quinoline-3-carbo­nitrile (2.0 g, 0.0051 mol) in conc. H2SO4 (20 mL) was stirred for 4 h at room temperature. Then the reaction mixture was poured into ice-cold water. The formed precipitate was collected, filtered off, washed with water and recrystallized from ethanol as pale-yellow crystals; yield 73%, m.p. 518 K.

4-(4-Meth­oxy­phen­yl)-1-(4-methyl-phen­yl)-2,5-dioxo-1,2,5,6,7,8-hexa­hydro­quinoline-3-carbo­nitrile, II

To a solution of 1,3-cyclohexa­nedione (3.36 g, 0.03 mol) and p-toluidine (3.21 g, 0.03 mol) in ethanol (40 ml), a catalytic amount of tri­ethyl­amine was added and the mixture was heated under reflux for 3 h. Ethyl-(2Z)-2-cyano-3-(4-meth­oxy­phen­yl)acrylate (6.93 g, 0.03 mol) was added to the reaction mixture while refluxing for another 3 h. The reaction mixture was then cooled to room temperature. The precipitate that formed was filtered off, dried and recrystallized from ethanol solution as orange crystals; yield 67%, m.p. 525 K.

Refinement  

Crystal data, data collection and structure refinement details are summarized in Table 3 ▸. For I, the hydrogen atoms of the NH2 group were found in the difference-Fourier map and refined freely. All C-bound H atoms were positioned geometrically (C—H = 0.93–0.98 Å) and refined as riding with U iso(H) = 1.2U eq(C) or 1.5U eq(C-meth­yl). For II, all H atoms were positioned geometrically (C—H = 0.95–1.00 Å) and refined as riding with U iso(H) = 1.2U eq(C) or 1.5U eq(C-meth­yl). For II, twenty reflections (4 15 10, 3 15 13, 3 14 16, 3 16 7, 3 16 8, 1 3 8, 2 3 0, Inline graphic 16 3, Inline graphic 4 10, 2 15 11, 0 14 8, 10 7 13, 1 16 11, 2 1 5, 3 16 4, Inline graphic 13 7, Inline graphic 16 4, 0 15 3, 1 16 10, Inline graphic 16 11) were omitted as clear outlier data. In II A, atoms C6A, C7A and C8A of the cyclo­hexane ring are disordered over two sets of sites in a 0.670 (11):0.330 (11) occupancy ratio. The coordinates and the U ij components of the C6A, C7A, C8A and the C6AA, C7AA and C8AA atoms were restrained using SADI and SIMU instructions.

Table 3. Experimental details.

  II II
Crystal data
Chemical formula C23H21ClN2O3 C24H22N2O3
M r 408.87 386.43
Crystal system, space group Orthorhombic, P b c a Monoclinic, P21/c
Temperature (K) 173 173
a, b, c (Å) 27.9446 (4), 8.4311 (1), 35.0101 (5) 10.3486 (2), 13.9969 (3), 27.5353 (5)
α, β, γ (°) 90, 90, 90 90, 93.797 (2), 90
V (Å3) 8248.51 (19) 3979.69 (14)
Z 16 8
Radiation type Cu Kα Cu Kα
μ (mm−1) 1.86 0.69
Crystal size (mm) 0.16 × 0.10 × 0.05 0.12 × 0.08 × 0.04
 
Data collection
Diffractometer Rigaku Oxford Diffraction Xcalibur, Eos, Gemini Rigaku Oxford Diffraction Xcalibur, Eos, Gemini
Absorption correction Multi-scan (CrysAlis PRO; Rigaku OD, 2015 ▸) Multi-scan (CrysAlis PRO; Rigaku OD, 2015 ▸)
T min, T max 0.614, 1.000 0.945, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections 64509, 7983, 6950 15107, 7579, 5380
R int 0.043 0.027
(sin θ/λ)max (Å−1) 0.615 0.615
 
Refinement
R[F 2 > 2σ(F 2)], wR(F 2), S 0.050, 0.132, 1.04 0.049, 0.139, 1.04
No. of reflections 7983 7579
No. of parameters 541 555
No. of restraints 0 36
H-atom treatment H atoms treated by a mixture of independent and constrained refinement H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.66, −0.55 0.25, −0.16
Open in a new tab

Computer programs: CrysAlis PRO (Rigaku OD, 2015 ▸), SHELXT (Sheldrick, 2015b ▸), SHELXL (Sheldrick, 2015a ▸) and OLEX2 (Dolomanov et al., 2009 ▸).

K values, which are large only for weak reflections with an F c/F cmax ratio less than 0.005 and less than 0.015 for I and II, respectively, were observed as 2.713 for I and 5.559 for II.

Supplementary Material

Crystal structure: contains datablock(s) I, II, global. DOI: 10.1107/S2056989021002140/yz2005sup1.cif

e-77-00351-sup1.cif (2.7MB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989021002140/yz2005Isup2.hkl

e-77-00351-Isup2.hkl (634.3KB, hkl)

Structure factors: contains datablock(s) II. DOI: 10.1107/S2056989021002140/yz2005IIsup3.hkl

e-77-00351-IIsup3.hkl (602KB, hkl)
Click here for additional data file. (7.4KB, cml)

Supporting information file. DOI: 10.1107/S2056989021002140/yz2005Isup4.cml

Click here for additional data file. (7.6KB, cml)

Supporting information file. DOI: 10.1107/S2056989021002140/yz2005IIsup5.cml

CCDC references: 2064688, 2064687

Additional supporting information: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

1-(4-Chlorophenyl)-4-(4-methylphenyl)-2,5-dioxo-1,2,5,6,7,8-hexahydroquinoline-3-carboxylic acid (I). Crystal data

C23H21ClN2O3 Dx = 1.317 Mg m−3
Mr = 408.87 Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, Pbca Cell parameters from 21280 reflections
a = 27.9446 (4) Å θ = 4.0–71.5°
b = 8.4311 (1) Å µ = 1.86 mm−1
c = 35.0101 (5) Å T = 173 K
V = 8248.51 (19) Å3 Prism, pale yellow
Z = 16 0.16 × 0.10 × 0.05 mm
F(000) = 3424
Open in a new tab

1-(4-Chlorophenyl)-4-(4-methylphenyl)-2,5-dioxo-1,2,5,6,7,8-hexahydroquinoline-3-carboxylic acid (I). Data collection

Rigaku Oxford Diffraction Xcalibur, Eos, Gemini diffractometer 7983 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Cu) X-ray Source 6950 reflections with I > 2σ(I)
Graphite monochromator Rint = 0.043
Detector resolution: 16.0416 pixels mm-1 θmax = 71.5°, θmin = 4.1°
ω scans h = −29→34
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2015) k = −10→6
Tmin = 0.614, Tmax = 1.000 l = −42→42
64509 measured reflections
Open in a new tab

1-(4-Chlorophenyl)-4-(4-methylphenyl)-2,5-dioxo-1,2,5,6,7,8-hexahydroquinoline-3-carboxylic acid (I). Refinement

Refinement on F2 Primary atom site location: dual
Least-squares matrix: full Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.050 H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.132 w = 1/[σ2(Fo2) + (0.0636P)2 + 5.5774P] where P = (Fo2 + 2Fc2)/3
S = 1.04 (Δ/σ)max < 0.001
7983 reflections Δρmax = 0.66 e Å−3
541 parameters Δρmin = −0.55 e Å−3
0 restraints
Open in a new tab

1-(4-Chlorophenyl)-4-(4-methylphenyl)-2,5-dioxo-1,2,5,6,7,8-hexahydroquinoline-3-carboxylic acid (I). Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
Open in a new tab

1-(4-Chlorophenyl)-4-(4-methylphenyl)-2,5-dioxo-1,2,5,6,7,8-hexahydroquinoline-3-carboxylic acid (I). Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
Cl1A 0.82611 (2) 0.31975 (8) 0.40005 (2) 0.0615 (2)
O1A 0.67114 (5) 0.01077 (15) 0.52217 (4) 0.0322 (3)
O2A 0.55412 (5) 0.09204 (16) 0.52328 (3) 0.0296 (3)
O3A 0.58223 (5) 0.60354 (17) 0.44478 (4) 0.0410 (3)
N1A 0.65291 (5) 0.26677 (17) 0.53641 (4) 0.0243 (3)
N2A 0.53741 (6) 0.0761 (2) 0.46051 (5) 0.0317 (4)
C1A 0.64987 (6) 0.1309 (2) 0.51400 (5) 0.0238 (3)
C2A 0.61843 (6) 0.1434 (2) 0.47878 (5) 0.0226 (3)
H2A 0.6294 0.0641 0.4603 0.027*
C3A 0.62358 (6) 0.3088 (2) 0.46017 (5) 0.0240 (3)
H3AA 0.5998 0.3194 0.4397 0.029*
C4A 0.61353 (6) 0.4304 (2) 0.49046 (5) 0.0249 (4)
C5A 0.59223 (7) 0.5801 (2) 0.47852 (6) 0.0312 (4)
C6A 0.58550 (10) 0.7071 (3) 0.50809 (7) 0.0469 (5)
H6AA 0.6119 0.7813 0.5065 0.056*
H6AB 0.5563 0.7649 0.5025 0.056*
C7A 0.58272 (10) 0.6436 (3) 0.54805 (7) 0.0498 (6)
H7AA 0.5526 0.5879 0.5513 0.060*
H7AB 0.5832 0.7316 0.5659 0.060*
C8A 0.62403 (8) 0.5307 (2) 0.55737 (5) 0.0340 (4)
H8AA 0.6535 0.5905 0.5596 0.041*
H8AB 0.6180 0.4790 0.5817 0.041*
C9A 0.62920 (6) 0.4077 (2) 0.52666 (5) 0.0241 (3)
C10A 0.67368 (6) 0.3265 (2) 0.44312 (5) 0.0253 (4)
C11A 0.68482 (8) 0.2534 (3) 0.40888 (6) 0.0398 (5)
H11A 0.6608 0.2039 0.3949 0.048*
C12A 0.73127 (9) 0.2530 (3) 0.39512 (7) 0.0476 (6)
H12A 0.7384 0.2024 0.3722 0.057*
C13A 0.76677 (7) 0.3277 (2) 0.41543 (6) 0.0368 (4)
C14A 0.75649 (8) 0.4059 (3) 0.44857 (6) 0.0434 (5)
H14A 0.7805 0.4579 0.4621 0.052*
C15A 0.70993 (8) 0.4069 (3) 0.46177 (6) 0.0395 (5)
H15A 0.7027 0.4632 0.4839 0.047*
C16A 0.68490 (6) 0.2579 (2) 0.56903 (5) 0.0268 (4)
C17A 0.67007 (7) 0.1859 (2) 0.60237 (5) 0.0341 (4)
H17A 0.6388 0.1494 0.6049 0.041*
C18A 0.70240 (8) 0.1686 (3) 0.63213 (6) 0.0440 (5)
H18A 0.6923 0.1219 0.6548 0.053*
C19A 0.74938 (9) 0.2194 (3) 0.62881 (6) 0.0452 (5)
C20A 0.76314 (8) 0.2944 (3) 0.59536 (7) 0.0448 (5)
H20A 0.7942 0.3326 0.5930 0.054*
C21A 0.73132 (7) 0.3134 (3) 0.56536 (6) 0.0375 (4)
H21A 0.7411 0.3630 0.5429 0.045*
C22A 0.56659 (6) 0.10306 (19) 0.48956 (5) 0.0228 (3)
C23A 0.78526 (12) 0.1889 (5) 0.66044 (9) 0.0773 (10)
H23A 0.7691 0.1890 0.6846 0.116*
H23B 0.8092 0.2707 0.6602 0.116*
H23C 0.8002 0.0878 0.6565 0.116*
Cl1B 0.69954 (3) 0.51675 (14) 0.24096 (2) 0.0960 (4)
O1B 0.47607 (5) 0.76223 (15) 0.29218 (4) 0.0334 (3)
O2B 0.43042 (5) 0.68918 (19) 0.37411 (4) 0.0401 (3)
O3B 0.54926 (5) 0.18004 (16) 0.38319 (4) 0.0376 (3)
N1B 0.45537 (5) 0.50593 (17) 0.30323 (4) 0.0246 (3)
N2B 0.49180 (7) 0.7000 (2) 0.41537 (5) 0.0335 (4)
C1B 0.47972 (6) 0.6448 (2) 0.31185 (5) 0.0240 (3)
C2B 0.50872 (6) 0.64104 (19) 0.34849 (5) 0.0219 (3)
H2B 0.5323 0.7270 0.3476 0.026*
C3B 0.53578 (6) 0.4824 (2) 0.35275 (5) 0.0228 (3)
H3BA 0.5485 0.4757 0.3788 0.027*
C4B 0.50099 (6) 0.3490 (2) 0.34697 (5) 0.0238 (3)
C5B 0.51222 (7) 0.1969 (2) 0.36457 (5) 0.0303 (4)
C6B 0.47826 (9) 0.0613 (2) 0.35856 (6) 0.0448 (5)
H6BA 0.4766 −0.0005 0.3819 0.054*
H6BB 0.4909 −0.0069 0.3387 0.054*
C7B 0.42824 (9) 0.1114 (3) 0.34759 (6) 0.0432 (5)
H7BA 0.4126 0.1589 0.3695 0.052*
H7BB 0.4099 0.0188 0.3401 0.052*
C8B 0.42911 (7) 0.2300 (2) 0.31484 (6) 0.0345 (4)
H8BA 0.4389 0.1766 0.2916 0.041*
H8BB 0.3972 0.2720 0.3109 0.041*
C9B 0.46301 (6) 0.3640 (2) 0.32309 (5) 0.0247 (3)
C10B 0.57756 (6) 0.4789 (2) 0.32494 (5) 0.0255 (4)
C11B 0.62165 (7) 0.5355 (3) 0.33652 (6) 0.0432 (5)
H11B 0.6260 0.5660 0.3618 0.052*
C12B 0.65946 (9) 0.5476 (4) 0.31115 (8) 0.0608 (8)
H12B 0.6890 0.5862 0.3192 0.073*
C13B 0.65256 (8) 0.5013 (3) 0.27362 (7) 0.0505 (6)
C14B 0.60972 (8) 0.4409 (3) 0.26148 (6) 0.0376 (4)
H14B 0.6058 0.4080 0.2363 0.045*
C15B 0.57242 (7) 0.4297 (2) 0.28716 (5) 0.0296 (4)
H15B 0.5433 0.3884 0.2791 0.035*
C16B 0.41761 (6) 0.5176 (2) 0.27496 (5) 0.0280 (4)
C17B 0.42624 (8) 0.4736 (3) 0.23774 (6) 0.0410 (5)
H17B 0.4561 0.4357 0.2305 0.049*
C18B 0.38942 (9) 0.4867 (4) 0.21121 (6) 0.0557 (7)
H18B 0.3950 0.4580 0.1859 0.067*
C19B 0.34492 (9) 0.5414 (4) 0.22167 (7) 0.0554 (7)
C20B 0.33726 (7) 0.5846 (3) 0.25939 (6) 0.0449 (5)
H20B 0.3073 0.6209 0.2668 0.054*
C21B 0.37358 (7) 0.5744 (3) 0.28612 (6) 0.0344 (4)
H21B 0.3683 0.6055 0.3113 0.041*
C22B 0.47312 (6) 0.6765 (2) 0.38092 (5) 0.0262 (4)
C23B 0.30543 (12) 0.5582 (7) 0.19237 (10) 0.1053 (16)
H23D 0.2808 0.4815 0.1975 0.158*
H23E 0.3183 0.5407 0.1673 0.158*
H23F 0.2921 0.6630 0.1938 0.158*
H2A2 0.5079 (9) 0.045 (3) 0.4652 (6) 0.031 (6)*
H2B1 0.4729 (9) 0.732 (3) 0.4330 (7) 0.037 (6)*
H2A1 0.5470 (9) 0.085 (3) 0.4374 (7) 0.038 (6)*
H2B2 0.5214 (10) 0.689 (3) 0.4200 (7) 0.043 (7)*
Open in a new tab

1-(4-Chlorophenyl)-4-(4-methylphenyl)-2,5-dioxo-1,2,5,6,7,8-hexahydroquinoline-3-carboxylic acid (I). Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
Cl1A 0.0364 (3) 0.0663 (4) 0.0816 (5) −0.0009 (3) 0.0225 (3) −0.0174 (3)
O1A 0.0331 (7) 0.0261 (7) 0.0375 (7) 0.0074 (5) −0.0058 (5) −0.0021 (5)
O2A 0.0288 (6) 0.0351 (7) 0.0251 (6) −0.0052 (5) 0.0032 (5) −0.0055 (5)
O3A 0.0462 (8) 0.0361 (8) 0.0406 (8) 0.0084 (6) −0.0093 (6) 0.0078 (6)
N1A 0.0246 (7) 0.0238 (7) 0.0246 (7) 0.0008 (6) −0.0018 (6) −0.0010 (6)
N2A 0.0252 (8) 0.0441 (10) 0.0259 (8) −0.0092 (7) −0.0025 (6) 0.0044 (7)
C1A 0.0209 (8) 0.0230 (8) 0.0276 (8) −0.0008 (7) 0.0020 (6) 0.0006 (7)
C2A 0.0230 (8) 0.0207 (8) 0.0240 (8) 0.0002 (6) 0.0005 (6) −0.0021 (6)
C3A 0.0257 (8) 0.0230 (8) 0.0233 (8) −0.0006 (7) −0.0023 (6) 0.0007 (6)
C4A 0.0243 (8) 0.0215 (8) 0.0288 (9) −0.0019 (7) 0.0021 (7) 0.0003 (7)
C5A 0.0297 (9) 0.0249 (9) 0.0391 (10) 0.0003 (7) −0.0009 (8) 0.0030 (8)
C6A 0.0615 (15) 0.0252 (10) 0.0542 (13) 0.0112 (10) −0.0046 (11) −0.0017 (9)
C7A 0.0705 (16) 0.0353 (11) 0.0437 (12) 0.0156 (11) 0.0062 (11) −0.0097 (9)
C8A 0.0460 (11) 0.0265 (9) 0.0294 (9) −0.0005 (8) 0.0033 (8) −0.0046 (7)
C9A 0.0236 (8) 0.0205 (8) 0.0283 (8) −0.0028 (6) 0.0028 (7) −0.0003 (7)
C10A 0.0281 (9) 0.0250 (8) 0.0229 (8) −0.0013 (7) 0.0002 (7) 0.0032 (6)
C11A 0.0408 (11) 0.0482 (12) 0.0305 (10) −0.0114 (10) 0.0021 (8) −0.0116 (9)
C12A 0.0474 (13) 0.0529 (13) 0.0423 (12) −0.0075 (11) 0.0142 (10) −0.0205 (10)
C13A 0.0316 (10) 0.0366 (10) 0.0423 (11) −0.0015 (8) 0.0097 (8) −0.0003 (8)
C14A 0.0335 (11) 0.0631 (14) 0.0336 (10) −0.0162 (10) 0.0034 (8) −0.0070 (10)
C15A 0.0371 (11) 0.0538 (13) 0.0275 (9) −0.0129 (9) 0.0060 (8) −0.0105 (9)
C16A 0.0271 (9) 0.0274 (9) 0.0257 (8) 0.0025 (7) −0.0035 (7) −0.0027 (7)
C17A 0.0283 (9) 0.0425 (11) 0.0314 (9) 0.0042 (8) 0.0018 (7) 0.0034 (8)
C18A 0.0493 (12) 0.0545 (13) 0.0282 (10) 0.0092 (10) −0.0039 (9) 0.0052 (9)
C19A 0.0477 (12) 0.0477 (13) 0.0402 (11) 0.0084 (10) −0.0178 (10) −0.0065 (10)
C20A 0.0309 (10) 0.0487 (13) 0.0548 (13) −0.0066 (9) −0.0126 (9) −0.0066 (10)
C21A 0.0344 (10) 0.0422 (11) 0.0360 (10) −0.0079 (9) −0.0036 (8) 0.0021 (9)
C22A 0.0242 (8) 0.0162 (7) 0.0279 (8) 0.0010 (6) 0.0011 (7) −0.0010 (6)
C23A 0.0704 (19) 0.097 (2) 0.0647 (18) 0.0068 (17) −0.0403 (16) 0.0008 (17)
Cl1B 0.0615 (4) 0.1578 (9) 0.0687 (5) −0.0455 (5) 0.0382 (4) −0.0341 (5)
O1B 0.0397 (7) 0.0276 (7) 0.0327 (7) −0.0015 (6) −0.0062 (6) 0.0098 (5)
O2B 0.0275 (7) 0.0539 (9) 0.0388 (7) 0.0046 (6) 0.0030 (6) −0.0066 (7)
O3B 0.0484 (8) 0.0321 (7) 0.0322 (7) 0.0089 (6) −0.0075 (6) 0.0075 (6)
N1B 0.0254 (7) 0.0244 (7) 0.0241 (7) −0.0002 (6) −0.0039 (6) 0.0020 (6)
N2B 0.0365 (9) 0.0389 (9) 0.0251 (8) 0.0098 (7) 0.0016 (7) −0.0039 (7)
C1B 0.0247 (8) 0.0236 (8) 0.0238 (8) 0.0017 (7) 0.0013 (6) 0.0018 (7)
C2B 0.0234 (8) 0.0186 (8) 0.0236 (8) 0.0000 (6) −0.0015 (6) 0.0001 (6)
C3B 0.0274 (8) 0.0218 (8) 0.0192 (7) 0.0037 (7) −0.0041 (6) −0.0011 (6)
C4B 0.0306 (9) 0.0204 (8) 0.0204 (8) 0.0023 (7) 0.0010 (6) 0.0000 (6)
C5B 0.0455 (11) 0.0231 (9) 0.0222 (8) 0.0049 (8) 0.0009 (8) 0.0004 (7)
C6B 0.0723 (16) 0.0214 (9) 0.0407 (11) −0.0050 (10) −0.0097 (11) 0.0064 (8)
C7B 0.0568 (14) 0.0321 (10) 0.0406 (11) −0.0195 (10) −0.0031 (10) 0.0044 (9)
C8B 0.0390 (10) 0.0299 (10) 0.0347 (10) −0.0085 (8) −0.0055 (8) 0.0011 (8)
C9B 0.0301 (9) 0.0219 (8) 0.0220 (8) 0.0003 (7) 0.0022 (7) 0.0001 (6)
C10B 0.0260 (8) 0.0245 (8) 0.0258 (8) 0.0036 (7) −0.0020 (7) −0.0021 (7)
C11B 0.0329 (10) 0.0629 (14) 0.0338 (10) −0.0063 (10) −0.0015 (8) −0.0183 (10)
C12B 0.0325 (11) 0.093 (2) 0.0563 (15) −0.0212 (13) 0.0061 (10) −0.0279 (14)
C13B 0.0378 (12) 0.0696 (16) 0.0441 (12) −0.0095 (11) 0.0146 (10) −0.0107 (11)
C14B 0.0399 (11) 0.0463 (11) 0.0267 (9) 0.0032 (9) 0.0028 (8) −0.0048 (8)
C15B 0.0283 (9) 0.0348 (10) 0.0256 (9) 0.0016 (8) −0.0032 (7) −0.0033 (7)
C16B 0.0280 (9) 0.0304 (9) 0.0257 (9) −0.0013 (7) −0.0049 (7) 0.0034 (7)
C17B 0.0364 (11) 0.0569 (13) 0.0296 (10) 0.0075 (10) −0.0037 (8) −0.0046 (9)
C18B 0.0534 (14) 0.0867 (19) 0.0269 (10) 0.0080 (13) −0.0111 (10) −0.0080 (11)
C19B 0.0399 (12) 0.089 (2) 0.0375 (12) 0.0031 (13) −0.0149 (10) 0.0056 (12)
C20B 0.0261 (10) 0.0658 (15) 0.0429 (12) 0.0036 (10) −0.0041 (8) 0.0047 (10)
C21B 0.0305 (10) 0.0441 (11) 0.0287 (9) −0.0003 (8) −0.0008 (7) 0.0028 (8)
C22B 0.0301 (9) 0.0193 (8) 0.0291 (9) 0.0029 (7) 0.0021 (7) 0.0013 (6)
C23B 0.0598 (19) 0.202 (5) 0.0542 (18) 0.023 (3) −0.0332 (15) −0.004 (2)
Open in a new tab

1-(4-Chlorophenyl)-4-(4-methylphenyl)-2,5-dioxo-1,2,5,6,7,8-hexahydroquinoline-3-carboxylic acid (I). Geometric parameters (Å, º)

Cl1A—C13A 1.745 (2) Cl1B—C13B 1.746 (2)
O1A—C1A 1.209 (2) O1B—C1B 1.210 (2)
O2A—C22A 1.234 (2) O2B—C22B 1.221 (2)
O3A—C5A 1.230 (2) O3B—C5B 1.232 (2)
N1A—C1A 1.391 (2) N1B—C1B 1.387 (2)
N1A—C9A 1.403 (2) N1B—C9B 1.400 (2)
N1A—C16A 1.452 (2) N1B—C16B 1.450 (2)
N2A—C22A 1.323 (2) N2B—C22B 1.329 (2)
N2A—H2A2 0.88 (2) N2B—H2B1 0.85 (3)
N2A—H2A1 0.86 (3) N2B—H2B2 0.85 (3)
C1A—C2A 1.518 (2) C1B—C2B 1.518 (2)
C2A—C22A 1.535 (2) C2B—C22B 1.539 (2)
C2A—C3A 1.546 (2) C2B—C3B 1.544 (2)
C2A—H2A 0.9800 C2B—H2B 0.9800
C3A—C4A 1.502 (2) C3B—C4B 1.500 (2)
C3A—C10A 1.529 (2) C3B—C10B 1.521 (2)
C3A—H3AA 0.9800 C3B—H3BA 0.9800
C4A—C9A 1.355 (3) C4B—C9B 1.357 (2)
C4A—C5A 1.456 (3) C4B—C5B 1.457 (2)
C5A—C6A 1.501 (3) C5B—C6B 1.500 (3)
C6A—C7A 1.500 (3) C6B—C7B 1.510 (3)
C6A—H6AA 0.9700 C6B—H6BA 0.9700
C6A—H6AB 0.9700 C6B—H6BB 0.9700
C7A—C8A 1.532 (3) C7B—C8B 1.522 (3)
C7A—H7AA 0.9700 C7B—H7BA 0.9700
C7A—H7AB 0.9700 C7B—H7BB 0.9700
C8A—C9A 1.500 (2) C8B—C9B 1.503 (3)
C8A—H8AA 0.9700 C8B—H8BA 0.9700
C8A—H8AB 0.9700 C8B—H8BB 0.9700
C10A—C15A 1.383 (3) C10B—C11B 1.382 (3)
C10A—C11A 1.383 (3) C10B—C15B 1.394 (2)
C11A—C12A 1.385 (3) C11B—C12B 1.384 (3)
C11A—H11A 0.9300 C11B—H11B 0.9300
C12A—C13A 1.373 (3) C12B—C13B 1.384 (3)
C12A—H12A 0.9300 C12B—H12B 0.9300
C13A—C14A 1.365 (3) C13B—C14B 1.369 (3)
C14A—C15A 1.381 (3) C14B—C15B 1.380 (3)
C14A—H14A 0.9300 C14B—H14B 0.9300
C15A—H15A 0.9300 C15B—H15B 0.9300
C16A—C17A 1.379 (3) C16B—C17B 1.376 (3)
C16A—C21A 1.385 (3) C16B—C21B 1.377 (3)
C17A—C18A 1.387 (3) C17B—C18B 1.391 (3)
C17A—H17A 0.9300 C17B—H17B 0.9300
C18A—C19A 1.386 (4) C18B—C19B 1.376 (4)
C18A—H18A 0.9300 C18B—H18B 0.9300
C19A—C20A 1.385 (3) C19B—C20B 1.386 (3)
C19A—C23A 1.516 (3) C19B—C23B 1.513 (3)
C20A—C21A 1.386 (3) C20B—C21B 1.383 (3)
C20A—H20A 0.9300 C20B—H20B 0.9300
C21A—H21A 0.9300 C21B—H21B 0.9300
C23A—H23A 0.9600 C23B—H23D 0.9600
C23A—H23B 0.9600 C23B—H23E 0.9600
C23A—H23C 0.9600 C23B—H23F 0.9600
C1A—N1A—C9A 122.11 (14) C1B—N1B—C9B 122.57 (14)
C1A—N1A—C16A 116.03 (14) C1B—N1B—C16B 116.61 (14)
C9A—N1A—C16A 121.72 (14) C9B—N1B—C16B 120.53 (14)
C22A—N2A—H2A2 118.9 (14) C22B—N2B—H2B1 117.2 (16)
C22A—N2A—H2A1 121.2 (16) C22B—N2B—H2B2 122.7 (17)
H2A2—N2A—H2A1 120 (2) H2B1—N2B—H2B2 120 (2)
O1A—C1A—N1A 121.78 (16) O1B—C1B—N1B 121.69 (16)
O1A—C1A—C2A 122.32 (16) O1B—C1B—C2B 122.89 (16)
N1A—C1A—C2A 115.90 (14) N1B—C1B—C2B 115.34 (14)
C1A—C2A—C22A 109.34 (14) C1B—C2B—C22B 105.92 (14)
C1A—C2A—C3A 110.54 (14) C1B—C2B—C3B 111.19 (13)
C22A—C2A—C3A 113.03 (14) C22B—C2B—C3B 114.42 (13)
C1A—C2A—H2A 107.9 C1B—C2B—H2B 108.4
C22A—C2A—H2A 107.9 C22B—C2B—H2B 108.4
C3A—C2A—H2A 107.9 C3B—C2B—H2B 108.4
C4A—C3A—C10A 112.35 (14) C4B—C3B—C10B 113.37 (14)
C4A—C3A—C2A 107.50 (14) C4B—C3B—C2B 108.59 (14)
C10A—C3A—C2A 109.75 (14) C10B—C3B—C2B 109.32 (14)
C4A—C3A—H3AA 109.1 C4B—C3B—H3BA 108.5
C10A—C3A—H3AA 109.1 C10B—C3B—H3BA 108.5
C2A—C3A—H3AA 109.1 C2B—C3B—H3BA 108.5
C9A—C4A—C5A 121.53 (16) C9B—C4B—C5B 120.72 (16)
C9A—C4A—C3A 120.26 (16) C9B—C4B—C3B 121.35 (15)
C5A—C4A—C3A 117.73 (16) C5B—C4B—C3B 117.59 (15)
O3A—C5A—C4A 120.51 (18) O3B—C5B—C4B 120.41 (17)
O3A—C5A—C6A 121.28 (18) O3B—C5B—C6B 121.21 (17)
C4A—C5A—C6A 118.12 (17) C4B—C5B—C6B 118.37 (17)
C7A—C6A—C5A 113.28 (18) C5B—C6B—C7B 114.10 (17)
C7A—C6A—H6AA 108.9 C5B—C6B—H6BA 108.7
C5A—C6A—H6AA 108.9 C7B—C6B—H6BA 108.7
C7A—C6A—H6AB 108.9 C5B—C6B—H6BB 108.7
C5A—C6A—H6AB 108.9 C7B—C6B—H6BB 108.7
H6AA—C6A—H6AB 107.7 H6BA—C6B—H6BB 107.6
C6A—C7A—C8A 112.44 (19) C6B—C7B—C8B 111.15 (18)
C6A—C7A—H7AA 109.1 C6B—C7B—H7BA 109.4
C8A—C7A—H7AA 109.1 C8B—C7B—H7BA 109.4
C6A—C7A—H7AB 109.1 C6B—C7B—H7BB 109.4
C8A—C7A—H7AB 109.1 C8B—C7B—H7BB 109.4
H7AA—C7A—H7AB 107.8 H7BA—C7B—H7BB 108.0
C9A—C8A—C7A 110.44 (17) C9B—C8B—C7B 111.05 (16)
C9A—C8A—H8AA 109.6 C9B—C8B—H8BA 109.4
C7A—C8A—H8AA 109.6 C7B—C8B—H8BA 109.4
C9A—C8A—H8AB 109.6 C9B—C8B—H8BB 109.4
C7A—C8A—H8AB 109.6 C7B—C8B—H8BB 109.4
H8AA—C8A—H8AB 108.1 H8BA—C8B—H8BB 108.0
C4A—C9A—N1A 120.00 (15) C4B—C9B—N1B 120.31 (16)
C4A—C9A—C8A 122.81 (16) C4B—C9B—C8B 122.79 (16)
N1A—C9A—C8A 117.15 (15) N1B—C9B—C8B 116.81 (15)
C15A—C10A—C11A 117.57 (17) C11B—C10B—C15B 118.23 (17)
C15A—C10A—C3A 122.30 (16) C11B—C10B—C3B 119.34 (16)
C11A—C10A—C3A 120.04 (16) C15B—C10B—C3B 122.30 (16)
C10A—C11A—C12A 120.90 (19) C10B—C11B—C12B 121.18 (19)
C10A—C11A—H11A 119.5 C10B—C11B—H11B 119.4
C12A—C11A—H11A 119.5 C12B—C11B—H11B 119.4
C13A—C12A—C11A 119.72 (19) C11B—C12B—C13B 118.8 (2)
C13A—C12A—H12A 120.1 C11B—C12B—H12B 120.6
C11A—C12A—H12A 120.1 C13B—C12B—H12B 120.6
C14A—C13A—C12A 120.63 (19) C14B—C13B—C12B 121.4 (2)
C14A—C13A—Cl1A 118.75 (17) C14B—C13B—Cl1B 118.84 (18)
C12A—C13A—Cl1A 120.60 (16) C12B—C13B—Cl1B 119.73 (18)
C13A—C14A—C15A 119.05 (19) C13B—C14B—C15B 118.95 (19)
C13A—C14A—H14A 120.5 C13B—C14B—H14B 120.5
C15A—C14A—H14A 120.5 C15B—C14B—H14B 120.5
C14A—C15A—C10A 121.97 (19) C14B—C15B—C10B 121.35 (18)
C14A—C15A—H15A 119.0 C14B—C15B—H15B 119.3
C10A—C15A—H15A 119.0 C10B—C15B—H15B 119.3
C17A—C16A—C21A 120.58 (17) C17B—C16B—C21B 121.26 (18)
C17A—C16A—N1A 120.22 (16) C17B—C16B—N1B 120.03 (17)
C21A—C16A—N1A 119.08 (16) C21B—C16B—N1B 118.71 (16)
C16A—C17A—C18A 119.10 (19) C16B—C17B—C18B 118.8 (2)
C16A—C17A—H17A 120.4 C16B—C17B—H17B 120.6
C18A—C17A—H17A 120.4 C18B—C17B—H17B 120.6
C19A—C18A—C17A 121.4 (2) C19B—C18B—C17B 121.2 (2)
C19A—C18A—H18A 119.3 C19B—C18B—H18B 119.4
C17A—C18A—H18A 119.3 C17B—C18B—H18B 119.4
C20A—C19A—C18A 118.36 (19) C18B—C19B—C20B 118.8 (2)
C20A—C19A—C23A 120.7 (2) C18B—C19B—C23B 120.7 (3)
C18A—C19A—C23A 120.9 (2) C20B—C19B—C23B 120.6 (3)
C19A—C20A—C21A 121.0 (2) C21B—C20B—C19B 121.0 (2)
C19A—C20A—H20A 119.5 C21B—C20B—H20B 119.5
C21A—C20A—H20A 119.5 C19B—C20B—H20B 119.5
C16A—C21A—C20A 119.4 (2) C16B—C21B—C20B 119.03 (19)
C16A—C21A—H21A 120.3 C16B—C21B—H21B 120.5
C20A—C21A—H21A 120.3 C20B—C21B—H21B 120.5
O2A—C22A—N2A 123.25 (16) O2B—C22B—N2B 123.20 (17)
O2A—C22A—C2A 121.21 (15) O2B—C22B—C2B 120.30 (16)
N2A—C22A—C2A 115.49 (15) N2B—C22B—C2B 116.41 (16)
C19A—C23A—H23A 109.5 C19B—C23B—H23D 109.5
C19A—C23A—H23B 109.5 C19B—C23B—H23E 109.5
H23A—C23A—H23B 109.5 H23D—C23B—H23E 109.5
C19A—C23A—H23C 109.5 C19B—C23B—H23F 109.5
H23A—C23A—H23C 109.5 H23D—C23B—H23F 109.5
H23B—C23A—H23C 109.5 H23E—C23B—H23F 109.5
Open in a new tab

1-(4-Chlorophenyl)-4-(4-methylphenyl)-2,5-dioxo-1,2,5,6,7,8-hexahydroquinoline-3-carboxylic acid (I). Hydrogen-bond geometry (Å, º)

D—H···A D—H H···A D···A D—H···A
N2A—H2A2···O2Ai 0.88 (2) 2.12 (3) 2.979 (2) 164 (2)
N2B—H2B1···O2Aii 0.86 (2) 2.26 (2) 3.055 (2) 154 (2)
N2A—H2A1···O3B 0.86 (2) 2.06 (2) 2.865 (2) 156 (2)
N2B—H2B2···O3A 0.85 (3) 2.04 (3) 2.847 (2) 159 (2)
C3A—H3AA···O3A 0.98 2.45 2.793 (2) 100
C8A—H8AB···O2Bii 0.97 2.50 3.392 (2) 153
C6B—H6BB···O1Biii 0.97 2.57 3.430 (2) 148
C14A—H14A···O1Aiv 0.93 2.54 3.393 (3) 153
C17A—H17A···O2Bii 0.93 2.48 3.110 (2) 125
C17B—H17B···O1Bv 0.93 2.52 3.424 (3) 164
Open in a new tab

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

4-(4-Methoxyphenyl)-1-(4-methylphenyl)-2,5-dioxo-1,2,5,6,7,8-hexahydroquinoline-3-carbonitrile (II). Crystal data

C24H22N2O3 F(000) = 1632
Mr = 386.43 Dx = 1.290 Mg m−3
Monoclinic, P21/c Cu Kα radiation, λ = 1.54184 Å
a = 10.3486 (2) Å Cell parameters from 3849 reflections
b = 13.9969 (3) Å θ = 4.3–70.8°
c = 27.5353 (5) Å µ = 0.69 mm−1
β = 93.797 (2)° T = 173 K
V = 3979.69 (14) Å3 Irregular, orange
Z = 8 0.12 × 0.08 × 0.04 mm
Open in a new tab

4-(4-Methoxyphenyl)-1-(4-methylphenyl)-2,5-dioxo-1,2,5,6,7,8-hexahydroquinoline-3-carbonitrile (II). Data collection

Rigaku Oxford Diffraction Xcalibur, Eos, Gemini diffractometer 5380 reflections with I > 2σ(I)
Detector resolution: 16.0416 pixels mm-1 Rint = 0.027
ω scans θmax = 71.4°, θmin = 3.5°
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2015) h = −9→12
Tmin = 0.945, Tmax = 1.000 k = −10→16
15107 measured reflections l = −26→33
7579 independent reflections
Open in a new tab

4-(4-Methoxyphenyl)-1-(4-methylphenyl)-2,5-dioxo-1,2,5,6,7,8-hexahydroquinoline-3-carbonitrile (II). Refinement

Refinement on F2 Primary atom site location: dual
Least-squares matrix: full Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049 H-atom parameters constrained
wR(F2) = 0.139 w = 1/[σ2(Fo2) + (0.0628P)2 + 0.1965P] where P = (Fo2 + 2Fc2)/3
S = 1.03 (Δ/σ)max < 0.001
7579 reflections Δρmax = 0.25 e Å−3
555 parameters Δρmin = −0.16 e Å−3
36 restraints
Open in a new tab

4-(4-Methoxyphenyl)-1-(4-methylphenyl)-2,5-dioxo-1,2,5,6,7,8-hexahydroquinoline-3-carbonitrile (II). Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
Open in a new tab

4-(4-Methoxyphenyl)-1-(4-methylphenyl)-2,5-dioxo-1,2,5,6,7,8-hexahydroquinoline-3-carbonitrile (II). Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq Occ. (<1)
O1A 0.36261 (17) 0.53971 (14) 0.33466 (6) 0.0704 (5)
O2A 0.78343 (15) 0.78301 (13) 0.24000 (6) 0.0635 (4)
O3A 0.5360 (2) 0.99458 (16) 0.43140 (8) 0.0866 (6)
N1A 0.40024 (16) 0.60665 (14) 0.26190 (6) 0.0490 (4)
N2A 0.6257 (3) 0.56408 (18) 0.41665 (8) 0.0773 (6)
C1A 0.4369 (2) 0.57641 (15) 0.30847 (7) 0.0502 (5)
C2A 0.5814 (2) 0.58943 (16) 0.32306 (7) 0.0499 (5)
H2A 0.628554 0.537522 0.306612 0.060*
C3A 0.63700 (18) 0.68516 (15) 0.30610 (7) 0.0462 (4)
H3A 0.733419 0.678557 0.307960 0.055*
C4A 0.59327 (19) 0.69818 (15) 0.25308 (7) 0.0440 (4)
C5A 0.6773 (2) 0.75536 (16) 0.22368 (8) 0.0509 (5)
C6A 0.6240 (7) 0.7794 (6) 0.1737 (2) 0.093 (3) 0.670 (11)
H6A1 0.647523 0.846564 0.167295 0.112* 0.670 (11)
H6A2 0.669856 0.739274 0.150722 0.112* 0.670 (11)
C7A 0.4928 (5) 0.7699 (5) 0.16172 (18) 0.0727 (19) 0.670 (11)
H7A1 0.478234 0.768970 0.125825 0.087* 0.670 (11)
H7A2 0.447588 0.826567 0.173844 0.087* 0.670 (11)
C8A 0.4343 (10) 0.6823 (10) 0.1818 (3) 0.058 (3) 0.670 (11)
H8A1 0.454564 0.627035 0.161223 0.070* 0.670 (11)
H8A2 0.338993 0.689814 0.180160 0.070* 0.670 (11)
C6AA 0.6417 (13) 0.7776 (12) 0.1706 (4) 0.081 (6) 0.330 (11)
H6A3 0.609006 0.843920 0.167569 0.097* 0.330 (11)
H6A4 0.719692 0.772369 0.151825 0.097* 0.330 (11)
C7AA 0.5411 (9) 0.7106 (9) 0.1504 (2) 0.062 (3) 0.330 (11)
H7A3 0.587817 0.655632 0.137269 0.074* 0.330 (11)
H7A4 0.496696 0.743252 0.122131 0.074* 0.330 (11)
C8AA 0.4327 (18) 0.668 (2) 0.1804 (5) 0.054 (5) 0.330 (11)
H8A3 0.354750 0.708882 0.177077 0.064* 0.330 (11)
H8A4 0.408875 0.603398 0.167990 0.064* 0.330 (11)
C9A 0.48142 (19) 0.66155 (15) 0.23353 (7) 0.0454 (4)
C10A 0.60548 (19) 0.76995 (15) 0.33746 (7) 0.0453 (4)
C11A 0.6939 (2) 0.79817 (18) 0.37505 (8) 0.0580 (5)
H11A 0.773514 0.764736 0.380089 0.070*
C12A 0.6683 (2) 0.8734 (2) 0.40504 (9) 0.0664 (6)
H12A 0.730490 0.891710 0.430239 0.080*
C13A 0.5529 (2) 0.92254 (17) 0.39877 (9) 0.0594 (6)
C14A 0.4648 (2) 0.89723 (17) 0.36131 (9) 0.0588 (5)
H14A 0.385742 0.931387 0.356279 0.071*
C15A 0.4919 (2) 0.82139 (17) 0.33077 (8) 0.0528 (5)
H15A 0.430961 0.804786 0.304833 0.063*
C16A 0.2677 (2) 0.58533 (16) 0.24393 (7) 0.0478 (5)
C17A 0.2392 (2) 0.50222 (18) 0.21912 (10) 0.0633 (6)
H17A 0.305254 0.456910 0.214024 0.076*
C18A 0.1124 (3) 0.48517 (19) 0.20156 (10) 0.0689 (7)
H18A 0.092331 0.427678 0.184344 0.083*
C19A 0.0151 (2) 0.55004 (18) 0.20862 (8) 0.0574 (5)
C20A 0.0455 (2) 0.63227 (18) 0.23423 (8) 0.0568 (5)
H20A −0.020731 0.677108 0.239908 0.068*
C21A 0.1721 (2) 0.65056 (16) 0.25189 (7) 0.0521 (5)
H21A 0.192371 0.707754 0.269352 0.062*
C22A 0.6045 (2) 0.57437 (17) 0.37597 (8) 0.0578 (5)
C23A 0.4110 (3) 1.0295 (3) 0.43679 (13) 0.0962 (10)
H23A 0.378518 1.060752 0.406571 0.144*
H23B 0.413342 1.075712 0.463558 0.144*
H23C 0.353668 0.976341 0.444030 0.144*
C24A −0.1230 (3) 0.5333 (2) 0.18813 (11) 0.0803 (8)
H24A −0.183518 0.561316 0.210066 0.120*
H24B −0.139106 0.464541 0.185086 0.120*
H24C −0.135458 0.563409 0.156018 0.120*
O1B 0.88611 (15) 0.55891 (11) 0.33264 (6) 0.0597 (4)
O2B 1.17002 (16) 0.19933 (11) 0.42029 (6) 0.0623 (4)
O3B 0.61297 (18) 0.20781 (13) 0.49274 (7) 0.0735 (5)
N1B 1.05243 (16) 0.52114 (12) 0.38701 (6) 0.0442 (4)
N2B 0.7586 (3) 0.37087 (19) 0.27435 (9) 0.0866 (8)
C1B 0.96338 (19) 0.50067 (15) 0.34912 (7) 0.0445 (4)
C2B 0.9722 (2) 0.40016 (16) 0.32852 (7) 0.0473 (5)
H2B 1.045583 0.399447 0.306669 0.057*
C3B 0.99990 (19) 0.32262 (14) 0.36769 (7) 0.0445 (4)
H3B 1.028406 0.263711 0.350848 0.053*
C4B 1.11285 (18) 0.35722 (14) 0.40066 (6) 0.0409 (4)
C5B 1.19280 (19) 0.28396 (15) 0.42658 (7) 0.0459 (4)
C6B 1.3012 (2) 0.31731 (17) 0.46160 (8) 0.0566 (5)
H6BA 1.372469 0.270099 0.462105 0.068*
H6BB 1.269539 0.320138 0.494725 0.068*
C7B 1.3531 (2) 0.41394 (17) 0.44876 (8) 0.0546 (5)
H7BA 1.398831 0.408795 0.418402 0.066*
H7BB 1.416456 0.435436 0.475017 0.066*
C8B 1.2457 (2) 0.48714 (16) 0.44186 (7) 0.0496 (5)
H8BA 1.213782 0.503444 0.473927 0.060*
H8BB 1.280653 0.546139 0.427828 0.060*
C9B 1.13513 (18) 0.45094 (14) 0.40896 (6) 0.0409 (4)
C10B 0.88665 (18) 0.29520 (14) 0.39738 (7) 0.0438 (4)
C11B 0.8175 (2) 0.36257 (15) 0.42189 (8) 0.0490 (5)
H11B 0.834148 0.428504 0.417023 0.059*
C12B 0.7244 (2) 0.33612 (16) 0.45338 (8) 0.0529 (5)
H12B 0.677947 0.383529 0.469731 0.064*
C13B 0.6998 (2) 0.24062 (16) 0.46077 (8) 0.0524 (5)
C14B 0.7626 (2) 0.17243 (16) 0.43470 (9) 0.0596 (6)
H14B 0.742172 0.106745 0.438278 0.072*
C15B 0.8550 (2) 0.19959 (16) 0.40346 (8) 0.0552 (5)
H15B 0.897639 0.152078 0.385788 0.066*
C16B 1.05339 (19) 0.61852 (14) 0.40490 (7) 0.0439 (4)
C17B 1.0002 (2) 0.64075 (17) 0.44792 (8) 0.0591 (5)
H17B 0.964595 0.591822 0.466862 0.071*
C18B 0.9988 (3) 0.73479 (19) 0.46353 (9) 0.0659 (6)
H18B 0.963120 0.749395 0.493561 0.079*
C19B 1.0478 (2) 0.80763 (17) 0.43663 (9) 0.0593 (6)
C20B 1.1019 (3) 0.78322 (18) 0.39393 (10) 0.0700 (7)
H20B 1.137513 0.831935 0.374852 0.084*
C21B 1.1056 (3) 0.68946 (17) 0.37820 (8) 0.0617 (6)
H21B 1.144360 0.674336 0.348844 0.074*
C22B 0.8523 (2) 0.38295 (17) 0.29799 (8) 0.0599 (6)
C23B 0.5890 (3) 0.2675 (2) 0.53236 (9) 0.0676 (6)
H23D 0.541756 0.324436 0.520484 0.101*
H23E 0.671532 0.286706 0.549044 0.101*
H23F 0.537152 0.232836 0.555109 0.101*
C24B 1.0432 (3) 0.9097 (2) 0.45374 (13) 0.0892 (9)
H24D 0.989531 0.913847 0.481671 0.134*
H24E 1.006030 0.950037 0.427298 0.134*
H24F 1.131171 0.931536 0.463385 0.134*
Open in a new tab

4-(4-Methoxyphenyl)-1-(4-methylphenyl)-2,5-dioxo-1,2,5,6,7,8-hexahydroquinoline-3-carbonitrile (II). Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
O1A 0.0649 (10) 0.0884 (13) 0.0588 (9) −0.0090 (9) 0.0108 (8) 0.0254 (9)
O2A 0.0504 (9) 0.0733 (11) 0.0676 (10) −0.0076 (8) 0.0095 (7) 0.0054 (8)
O3A 0.0840 (13) 0.0771 (13) 0.0989 (14) −0.0122 (10) 0.0082 (11) −0.0350 (11)
N1A 0.0440 (9) 0.0576 (10) 0.0458 (9) −0.0023 (7) 0.0052 (7) 0.0081 (7)
N2A 0.1003 (18) 0.0772 (15) 0.0541 (12) 0.0104 (13) 0.0028 (11) 0.0156 (10)
C1A 0.0551 (12) 0.0493 (11) 0.0472 (10) 0.0038 (9) 0.0099 (9) 0.0094 (9)
C2A 0.0532 (12) 0.0510 (12) 0.0457 (10) 0.0118 (9) 0.0045 (9) 0.0089 (9)
C3A 0.0378 (9) 0.0527 (11) 0.0482 (10) 0.0077 (8) 0.0025 (8) 0.0105 (9)
C4A 0.0429 (10) 0.0475 (11) 0.0425 (10) 0.0094 (8) 0.0077 (8) 0.0061 (8)
C5A 0.0464 (11) 0.0552 (12) 0.0522 (11) 0.0016 (9) 0.0115 (9) 0.0026 (9)
C6A 0.095 (5) 0.129 (6) 0.055 (4) −0.062 (4) −0.002 (3) 0.049 (4)
C7A 0.069 (3) 0.097 (4) 0.051 (2) −0.014 (3) −0.0021 (19) 0.029 (2)
C8A 0.058 (4) 0.069 (5) 0.046 (4) −0.003 (3) −0.009 (3) 0.002 (2)
C6AA 0.065 (7) 0.122 (12) 0.058 (8) 0.023 (7) 0.014 (6) −0.023 (7)
C7AA 0.066 (5) 0.084 (7) 0.035 (3) −0.013 (5) 0.008 (3) 0.006 (3)
C8AA 0.052 (8) 0.075 (9) 0.037 (7) −0.018 (6) 0.024 (6) 0.010 (5)
C9A 0.0445 (10) 0.0503 (11) 0.0421 (10) 0.0058 (8) 0.0088 (8) 0.0049 (8)
C10A 0.0411 (10) 0.0502 (11) 0.0445 (10) −0.0005 (8) 0.0026 (8) 0.0100 (8)
C11A 0.0454 (11) 0.0657 (14) 0.0616 (13) 0.0010 (10) −0.0051 (10) 0.0044 (11)
C12A 0.0593 (14) 0.0718 (16) 0.0664 (14) −0.0142 (12) −0.0085 (11) −0.0072 (12)
C13A 0.0596 (13) 0.0534 (13) 0.0660 (13) −0.0135 (10) 0.0094 (11) −0.0063 (10)
C14A 0.0508 (12) 0.0572 (13) 0.0686 (14) 0.0063 (10) 0.0046 (10) 0.0008 (11)
C15A 0.0466 (11) 0.0570 (12) 0.0538 (11) 0.0030 (9) −0.0048 (9) 0.0006 (9)
C16A 0.0449 (10) 0.0540 (12) 0.0451 (10) −0.0013 (9) 0.0082 (8) 0.0076 (9)
C17A 0.0542 (13) 0.0550 (13) 0.0811 (16) 0.0032 (10) 0.0071 (11) −0.0048 (12)
C18A 0.0643 (15) 0.0568 (14) 0.0847 (17) −0.0078 (11) −0.0007 (13) −0.0096 (12)
C19A 0.0530 (12) 0.0643 (14) 0.0552 (12) −0.0051 (10) 0.0048 (10) 0.0117 (10)
C20A 0.0523 (12) 0.0664 (14) 0.0523 (11) 0.0096 (10) 0.0085 (9) 0.0076 (10)
C21A 0.0571 (12) 0.0535 (12) 0.0459 (10) 0.0008 (10) 0.0055 (9) 0.0016 (9)
C22A 0.0637 (14) 0.0543 (13) 0.0555 (13) 0.0103 (10) 0.0039 (10) 0.0096 (10)
C23A 0.090 (2) 0.094 (2) 0.106 (2) 0.0119 (18) 0.0168 (18) −0.0366 (19)
C24A 0.0576 (15) 0.095 (2) 0.0873 (19) −0.0087 (14) −0.0062 (13) 0.0090 (16)
O1B 0.0548 (9) 0.0560 (9) 0.0661 (9) 0.0093 (7) −0.0118 (7) 0.0051 (7)
O2B 0.0607 (9) 0.0479 (9) 0.0773 (10) 0.0092 (7) −0.0046 (8) 0.0018 (7)
O3B 0.0720 (11) 0.0662 (11) 0.0845 (12) −0.0222 (9) 0.0214 (9) −0.0025 (9)
N1B 0.0465 (9) 0.0438 (9) 0.0420 (8) 0.0044 (7) 0.0004 (7) −0.0016 (7)
N2B 0.0919 (17) 0.0799 (16) 0.0825 (15) −0.0069 (13) −0.0364 (14) −0.0028 (12)
C1B 0.0426 (10) 0.0496 (11) 0.0412 (9) 0.0033 (8) 0.0011 (8) 0.0045 (8)
C2B 0.0483 (11) 0.0565 (12) 0.0367 (9) 0.0033 (9) −0.0003 (8) −0.0037 (8)
C3B 0.0472 (10) 0.0443 (10) 0.0418 (9) 0.0072 (8) 0.0007 (8) −0.0078 (8)
C4B 0.0386 (9) 0.0482 (11) 0.0361 (9) 0.0049 (8) 0.0049 (7) −0.0014 (8)
C5B 0.0437 (10) 0.0489 (12) 0.0453 (10) 0.0067 (8) 0.0062 (8) −0.0010 (8)
C6B 0.0526 (12) 0.0586 (13) 0.0572 (12) 0.0100 (10) −0.0076 (10) 0.0048 (10)
C7B 0.0434 (11) 0.0633 (14) 0.0558 (11) 0.0018 (9) −0.0065 (9) −0.0036 (10)
C8B 0.0485 (11) 0.0517 (12) 0.0478 (10) 0.0006 (9) −0.0023 (9) −0.0035 (9)
C9B 0.0402 (9) 0.0487 (11) 0.0342 (8) 0.0048 (8) 0.0051 (7) −0.0017 (7)
C10B 0.0409 (9) 0.0455 (10) 0.0439 (9) 0.0006 (8) −0.0058 (8) −0.0040 (8)
C11B 0.0501 (11) 0.0409 (10) 0.0562 (11) −0.0020 (8) 0.0052 (9) −0.0017 (9)
C12B 0.0498 (11) 0.0520 (12) 0.0575 (12) −0.0008 (9) 0.0070 (9) −0.0061 (9)
C13B 0.0458 (11) 0.0551 (12) 0.0557 (11) −0.0101 (9) −0.0001 (9) 0.0018 (9)
C14B 0.0625 (13) 0.0432 (11) 0.0726 (14) −0.0109 (10) 0.0000 (11) −0.0026 (10)
C15B 0.0570 (13) 0.0439 (11) 0.0641 (13) 0.0013 (9) −0.0010 (10) −0.0111 (9)
C16B 0.0420 (10) 0.0467 (11) 0.0428 (9) 0.0054 (8) 0.0006 (8) 0.0003 (8)
C17B 0.0657 (14) 0.0561 (13) 0.0573 (12) −0.0059 (11) 0.0186 (10) −0.0036 (10)
C18B 0.0691 (15) 0.0678 (16) 0.0625 (14) 0.0010 (12) 0.0173 (12) −0.0212 (12)
C19B 0.0551 (12) 0.0513 (13) 0.0697 (14) 0.0069 (10) −0.0090 (11) −0.0095 (11)
C20B 0.0912 (19) 0.0468 (13) 0.0725 (15) −0.0048 (12) 0.0084 (14) 0.0094 (11)
C21B 0.0829 (16) 0.0534 (13) 0.0507 (12) 0.0017 (12) 0.0184 (11) 0.0030 (10)
C22B 0.0708 (15) 0.0574 (13) 0.0497 (11) 0.0034 (11) −0.0101 (11) −0.0021 (10)
C23B 0.0629 (14) 0.0806 (17) 0.0601 (13) −0.0064 (13) 0.0093 (11) 0.0109 (12)
C24B 0.093 (2) 0.0580 (16) 0.114 (2) 0.0077 (15) −0.0134 (18) −0.0221 (16)
Open in a new tab

4-(4-Methoxyphenyl)-1-(4-methylphenyl)-2,5-dioxo-1,2,5,6,7,8-hexahydroquinoline-3-carbonitrile (II). Geometric parameters (Å, º)

O1A—C1A 1.204 (3) C23A—H23B 0.9800
O2A—C5A 1.222 (3) C23A—H23C 0.9800
O3A—C13A 1.369 (3) C24A—H24A 0.9800
O3A—C23A 1.400 (4) C24A—H24B 0.9800
N1A—C1A 1.380 (3) C24A—H24C 0.9800
N1A—C9A 1.412 (3) O1B—C1B 1.209 (2)
N1A—C16A 1.458 (3) O2B—C5B 1.218 (3)
N2A—C22A 1.136 (3) O3B—C13B 1.378 (3)
C1A—C2A 1.533 (3) O3B—C23B 1.409 (3)
C2A—C22A 1.476 (3) N1B—C1B 1.376 (3)
C2A—C3A 1.543 (3) N1B—C9B 1.412 (3)
C2A—H2A 1.0000 N1B—C16B 1.449 (3)
C3A—C4A 1.510 (3) N2B—C22B 1.145 (3)
C3A—C10A 1.516 (3) C1B—C2B 1.522 (3)
C3A—H3A 1.0000 C2B—C22B 1.471 (3)
C4A—C9A 1.345 (3) C2B—C3B 1.544 (3)
C4A—C5A 1.465 (3) C2B—H2B 1.0000
C5A—C6A 1.487 (6) C3B—C4B 1.511 (3)
C5A—C6AA 1.515 (13) C3B—C10B 1.522 (3)
C6A—C7A 1.382 (7) C3B—H3B 1.0000
C6A—H6A1 0.9900 C4B—C9B 1.349 (3)
C6A—H6A2 0.9900 C4B—C5B 1.472 (3)
C7A—C8A 1.490 (10) C5B—C6B 1.504 (3)
C7A—H7A1 0.9900 C6B—C7B 1.506 (3)
C7A—H7A2 0.9900 C6B—H6BA 0.9900
C8A—C9A 1.503 (7) C6B—H6BB 0.9900
C8A—H8A1 0.9900 C7B—C8B 1.514 (3)
C8A—H8A2 0.9900 C7B—H7BA 0.9900
C6AA—C7AA 1.481 (13) C7B—H7BB 0.9900
C6AA—H6A3 0.9900 C8B—C9B 1.500 (3)
C6AA—H6A4 0.9900 C8B—H8BA 0.9900
C7AA—C8AA 1.556 (13) C8B—H8BB 0.9900
C7AA—H7A3 0.9900 C10B—C11B 1.386 (3)
C7AA—H7A4 0.9900 C10B—C15B 1.391 (3)
C8AA—C9A 1.518 (14) C11B—C12B 1.388 (3)
C8AA—H8A3 0.9900 C11B—H11B 0.9500
C8AA—H8A4 0.9900 C12B—C13B 1.378 (3)
C10A—C15A 1.380 (3) C12B—H12B 0.9500
C10A—C11A 1.392 (3) C13B—C14B 1.382 (3)
C11A—C12A 1.375 (4) C14B—C15B 1.381 (3)
C11A—H11A 0.9500 C14B—H14B 0.9500
C12A—C13A 1.379 (4) C15B—H15B 0.9500
C12A—H12A 0.9500 C16B—C21B 1.368 (3)
C13A—C14A 1.377 (3) C16B—C17B 1.374 (3)
C14A—C15A 1.394 (3) C17B—C18B 1.385 (3)
C14A—H14A 0.9500 C17B—H17B 0.9500
C15A—H15A 0.9500 C18B—C19B 1.376 (4)
C16A—C17A 1.371 (3) C18B—H18B 0.9500
C16A—C21A 1.374 (3) C19B—C20B 1.378 (4)
C17A—C18A 1.388 (4) C19B—C24B 1.506 (3)
C17A—H17A 0.9500 C20B—C21B 1.383 (4)
C18A—C19A 1.380 (4) C20B—H20B 0.9500
C18A—H18A 0.9500 C21B—H21B 0.9500
C19A—C20A 1.375 (4) C23B—H23D 0.9800
C19A—C24A 1.519 (3) C23B—H23E 0.9800
C20A—C21A 1.391 (3) C23B—H23F 0.9800
C20A—H20A 0.9500 C24B—H24D 0.9800
C21A—H21A 0.9500 C24B—H24E 0.9800
C23A—H23A 0.9800 C24B—H24F 0.9800
C13A—O3A—C23A 119.0 (2) O3A—C23A—H23B 109.5
C1A—N1A—C9A 122.95 (18) H23A—C23A—H23B 109.5
C1A—N1A—C16A 116.59 (17) O3A—C23A—H23C 109.5
C9A—N1A—C16A 120.30 (16) H23A—C23A—H23C 109.5
O1A—C1A—N1A 122.7 (2) H23B—C23A—H23C 109.5
O1A—C1A—C2A 123.00 (19) C19A—C24A—H24A 109.5
N1A—C1A—C2A 114.25 (17) C19A—C24A—H24B 109.5
C22A—C2A—C1A 109.44 (18) H24A—C24A—H24B 109.5
C22A—C2A—C3A 112.57 (19) C19A—C24A—H24C 109.5
C1A—C2A—C3A 113.61 (16) H24A—C24A—H24C 109.5
C22A—C2A—H2A 106.9 H24B—C24A—H24C 109.5
C1A—C2A—H2A 106.9 C13B—O3B—C23B 116.91 (19)
C3A—C2A—H2A 106.9 C1B—N1B—C9B 122.42 (17)
C4A—C3A—C10A 113.21 (16) C1B—N1B—C16B 116.28 (16)
C4A—C3A—C2A 107.67 (17) C9B—N1B—C16B 121.24 (15)
C10A—C3A—C2A 114.14 (17) O1B—C1B—N1B 122.5 (2)
C4A—C3A—H3A 107.1 O1B—C1B—C2B 122.54 (18)
C10A—C3A—H3A 107.1 N1B—C1B—C2B 114.93 (16)
C2A—C3A—H3A 107.1 C22B—C2B—C1B 107.18 (18)
C9A—C4A—C5A 120.91 (18) C22B—C2B—C3B 113.26 (19)
C9A—C4A—C3A 122.37 (18) C1B—C2B—C3B 113.74 (15)
C5A—C4A—C3A 116.70 (18) C22B—C2B—H2B 107.5
O2A—C5A—C4A 121.5 (2) C1B—C2B—H2B 107.5
O2A—C5A—C6A 122.6 (3) C3B—C2B—H2B 107.5
C4A—C5A—C6A 116.0 (3) C4B—C3B—C10B 110.53 (15)
O2A—C5A—C6AA 116.4 (6) C4B—C3B—C2B 107.16 (17)
C4A—C5A—C6AA 122.0 (6) C10B—C3B—C2B 116.00 (16)
C7A—C6A—C5A 119.8 (5) C4B—C3B—H3B 107.6
C7A—C6A—H6A1 107.4 C10B—C3B—H3B 107.6
C5A—C6A—H6A1 107.4 C2B—C3B—H3B 107.6
C7A—C6A—H6A2 107.4 C9B—C4B—C5B 120.73 (17)
C5A—C6A—H6A2 107.4 C9B—C4B—C3B 122.01 (17)
H6A1—C6A—H6A2 106.9 C5B—C4B—C3B 117.10 (18)
C6A—C7A—C8A 114.0 (6) O2B—C5B—C4B 120.75 (19)
C6A—C7A—H7A1 108.7 O2B—C5B—C6B 121.47 (19)
C8A—C7A—H7A1 108.7 C4B—C5B—C6B 117.77 (18)
C6A—C7A—H7A2 108.7 C5B—C6B—C7B 113.01 (18)
C8A—C7A—H7A2 108.7 C5B—C6B—H6BA 109.0
H7A1—C7A—H7A2 107.6 C7B—C6B—H6BA 109.0
C7A—C8A—C9A 113.4 (7) C5B—C6B—H6BB 109.0
C7A—C8A—H8A1 108.9 C7B—C6B—H6BB 109.0
C9A—C8A—H8A1 108.9 H6BA—C6B—H6BB 107.8
C7A—C8A—H8A2 108.9 C6B—C7B—C8B 111.51 (18)
C9A—C8A—H8A2 108.9 C6B—C7B—H7BA 109.3
H8A1—C8A—H8A2 107.7 C8B—C7B—H7BA 109.3
C7AA—C6AA—C5A 110.6 (11) C6B—C7B—H7BB 109.3
C7AA—C6AA—H6A3 109.5 C8B—C7B—H7BB 109.3
C5A—C6AA—H6A3 109.5 H7BA—C7B—H7BB 108.0
C7AA—C6AA—H6A4 109.5 C9B—C8B—C7B 111.81 (18)
C5A—C6AA—H6A4 109.5 C9B—C8B—H8BA 109.3
H6A3—C6AA—H6A4 108.1 C7B—C8B—H8BA 109.3
C6AA—C7AA—C8AA 123.9 (12) C9B—C8B—H8BB 109.3
C6AA—C7AA—H7A3 106.4 C7B—C8B—H8BB 109.3
C8AA—C7AA—H7A3 106.4 H8BA—C8B—H8BB 107.9
C6AA—C7AA—H7A4 106.4 C4B—C9B—N1B 120.81 (17)
C8AA—C7AA—H7A4 106.4 C4B—C9B—C8B 123.09 (18)
H7A3—C7AA—H7A4 106.4 N1B—C9B—C8B 116.10 (18)
C9A—C8AA—C7AA 109.2 (12) C11B—C10B—C15B 117.5 (2)
C9A—C8AA—H8A3 109.8 C11B—C10B—C3B 122.08 (18)
C7AA—C8AA—H8A3 109.8 C15B—C10B—C3B 120.23 (19)
C9A—C8AA—H8A4 109.8 C10B—C11B—C12B 121.7 (2)
C7AA—C8AA—H8A4 109.8 C10B—C11B—H11B 119.2
H8A3—C8AA—H8A4 108.3 C12B—C11B—H11B 119.2
C4A—C9A—N1A 120.92 (18) C13B—C12B—C11B 119.6 (2)
C4A—C9A—C8A 121.5 (4) C13B—C12B—H12B 120.2
N1A—C9A—C8A 117.5 (4) C11B—C12B—H12B 120.2
C4A—C9A—C8AA 125.8 (7) O3B—C13B—C12B 123.5 (2)
N1A—C9A—C8AA 113.1 (7) O3B—C13B—C14B 116.8 (2)
C15A—C10A—C11A 117.6 (2) C12B—C13B—C14B 119.7 (2)
C15A—C10A—C3A 123.09 (18) C15B—C14B—C13B 120.1 (2)
C11A—C10A—C3A 119.35 (18) C15B—C14B—H14B 119.9
C12A—C11A—C10A 121.4 (2) C13B—C14B—H14B 119.9
C12A—C11A—H11A 119.3 C14B—C15B—C10B 121.2 (2)
C10A—C11A—H11A 119.3 C14B—C15B—H15B 119.4
C11A—C12A—C13A 120.4 (2) C10B—C15B—H15B 119.4
C11A—C12A—H12A 119.8 C21B—C16B—C17B 119.6 (2)
C13A—C12A—H12A 119.8 C21B—C16B—N1B 119.62 (19)
O3A—C13A—C14A 125.0 (2) C17B—C16B—N1B 120.78 (19)
O3A—C13A—C12A 115.6 (2) C16B—C17B—C18B 119.7 (2)
C14A—C13A—C12A 119.4 (2) C16B—C17B—H17B 120.1
C13A—C14A—C15A 119.9 (2) C18B—C17B—H17B 120.1
C13A—C14A—H14A 120.1 C19B—C18B—C17B 121.7 (2)
C15A—C14A—H14A 120.1 C19B—C18B—H18B 119.2
C10A—C15A—C14A 121.4 (2) C17B—C18B—H18B 119.2
C10A—C15A—H15A 119.3 C18B—C19B—C20B 117.4 (2)
C14A—C15A—H15A 119.3 C18B—C19B—C24B 120.9 (3)
C17A—C16A—C21A 120.6 (2) C20B—C19B—C24B 121.7 (3)
C17A—C16A—N1A 120.6 (2) C19B—C20B—C21B 121.6 (2)
C21A—C16A—N1A 118.7 (2) C19B—C20B—H20B 119.2
C16A—C17A—C18A 119.1 (2) C21B—C20B—H20B 119.2
C16A—C17A—H17A 120.4 C16B—C21B—C20B 120.0 (2)
C18A—C17A—H17A 120.4 C16B—C21B—H21B 120.0
C19A—C18A—C17A 121.3 (2) C20B—C21B—H21B 120.0
C19A—C18A—H18A 119.3 N2B—C22B—C2B 179.0 (3)
C17A—C18A—H18A 119.3 O3B—C23B—H23D 109.5
C20A—C19A—C18A 118.6 (2) O3B—C23B—H23E 109.5
C20A—C19A—C24A 119.8 (2) H23D—C23B—H23E 109.5
C18A—C19A—C24A 121.6 (2) O3B—C23B—H23F 109.5
C19A—C20A—C21A 120.8 (2) H23D—C23B—H23F 109.5
C19A—C20A—H20A 119.6 H23E—C23B—H23F 109.5
C21A—C20A—H20A 119.6 C19B—C24B—H24D 109.5
C16A—C21A—C20A 119.5 (2) C19B—C24B—H24E 109.5
C16A—C21A—H21A 120.2 H24D—C24B—H24E 109.5
C20A—C21A—H21A 120.2 C19B—C24B—H24F 109.5
N2A—C22A—C2A 178.0 (3) H24D—C24B—H24F 109.5
O3A—C23A—H23A 109.5 H24E—C24B—H24F 109.5
Open in a new tab

4-(4-Methoxyphenyl)-1-(4-methylphenyl)-2,5-dioxo-1,2,5,6,7,8-hexahydroquinoline-3-carbonitrile (II). Hydrogen-bond geometry (Å, º)

Cg4 and Cg9 are the centroids of the C10A–C15A and C16B–C21B rings, respectively.

D—H···A D—H H···A D···A D—H···A
C21A—H21A···N2Bi 0.95 2.65 3.258 (4) 123
C14B—H14B···O3Aii 0.95 2.65 3.417 (3) 139
C3A—H3A···O1B 1.00 2.37 3.171 (2) 136
C23B—H23E···Cg9iii 0.98 2.93 3.868 (3) 160
C23B—H23F···Cg4iv 0.98 2.74 3.710 (3) 169
Open in a new tab

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

Funding Statement

This work was funded by National Science Foundation grant CHE-1039027.

References

  1. Abdel-Gawad, S. M., El-Gaby, M. S. A., Heiba, H. I., Aly, H. M. & Ghorab, M. M. (2005). Jnl Chin. Chem. Soc. 52, 1227–1236.
  2. Afzal, O., Kumar, S., Haider, M. R., Ali, M. R., Kumar, R., Jaggi, M. & Bawa, S. (2015). Eur. J. Med. Chem. 97, 871–910. [DOI] [PubMed]
  3. Asiri, A. M., Al-Youbi, A. O., Faidallah, H. M., Badahdah, K. O. & Ng, S. W. (2011). Acta Cryst. E67, o2597. [DOI] [PMC free article] [PubMed]
  4. Asiri, A. M., Faidallah, H. M., Saqer, A. A. A., Ng, S. W. & Tiekink, E. R. T. (2012). Acta Cryst. E68, o2291–o2292. [DOI] [PMC free article] [PubMed]
  5. Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.
  6. Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.
  7. Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341.
  8. Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. [DOI] [PMC free article] [PubMed]
  9. Kumar, S., Bawa, S. & Gupta, H. (2009). Mini Rev. Med. Chem. 9, 1648–1654. [DOI] [PubMed]
  10. Kurbanova, M. M., Huseynov, E. Z., Gurbanov, A. V., Maharramov, A. M. & Ng, S. W. (2012). Acta Cryst. E68, o2233. [DOI] [PMC free article] [PubMed]
  11. Mohamed, S. K., Akkurt, M., Jasinski, J. P., Allah, O. A. A. A. & Albayati, M. R. (2015). Acta Cryst. E71, o949–o950. [DOI] [PMC free article] [PubMed]
  12. Morales, A. D., García-Granda, S., Navarro, M. S., Diviú, A. M. & Pérez-Barquero, R. E. (1996). Acta Cryst. C52, 2356–2359.
  13. Muscia, G. C., Buldain, G. Y. & Asís, S. E. (2014). Eur. J. Med. Chem. 73, 243–249. [DOI] [PubMed]
  14. Praveen, C., DheenKumar, P., Muralidharan, D. & Perumal, P. T. (2010). Bioorg. Med. Chem. Lett. 20, 7292–7296. [DOI] [PubMed]
  15. Psomas, G. & Kessissoglou, D. P. (2013). Dalton Trans. 42, 6252–6276. [DOI] [PubMed]
  16. Guo, L. J., Wei, C. X., Jia, J. H., Zhao, L. M. & Quan, Z. S. (2009). Eur. J. Med. Chem. 44, 954–958. [DOI] [PubMed]
  17. Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.
  18. Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8.
  19. Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8.
  20. Venkat Reddy, G., Ravi Kanth, S., Maitraie, D., Narsaiah, B., Shanthan Rao, P., Hara Kishore, K., Murthy, U. S., Ravi, B., Ashok Kumar, B. & Parthasarathy, T. (2009). Eur. J. Med. Chem. 44, 1570–1578. [DOI] [PubMed]

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, global. DOI: 10.1107/S2056989021002140/yz2005sup1.cif

e-77-00351-sup1.cif (2.7MB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989021002140/yz2005Isup2.hkl

e-77-00351-Isup2.hkl (634.3KB, hkl)

Structure factors: contains datablock(s) II. DOI: 10.1107/S2056989021002140/yz2005IIsup3.hkl

e-77-00351-IIsup3.hkl (602KB, hkl)
Click here for additional data file. (7.4KB, cml)

Supporting information file. DOI: 10.1107/S2056989021002140/yz2005Isup4.cml

Click here for additional data file. (7.6KB, cml)

Supporting information file. DOI: 10.1107/S2056989021002140/yz2005IIsup5.cml

CCDC references: 2064688, 2064687

Additional supporting information: crystallographic information; 3D view; checkCIF report

Articles from Acta Crystallographica Section E: Crystallographic Communications are provided here courtesy of International Union of Crystallography

RESOURCES