organic compounds
Diethyl 7,7′-dichloro-4-oxo-4H-[1,4′-biquinoline]-3,3′-dicarboxylate
aSchool of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan
*Correspondence e-mail: ishi206@u-shizuoka-ken.ac.jp
In the title compound, C24H18Cl2N2O5, the quinoline and quinolinone moieties are nearly perpendicular to each other, forming a dihedral angle of 82.36 (3)°. In the crystal, molecules form a halogen bond between a Cl atom of a quinolinone moiety and the N atom of the quinoline moiety of the inversion equivalent [Cl⋯N = 3.106 (3) Å]. The molecules also form two kinds of C—H⋯O hydrogen-bonded centrosymmetric inversion dimers, making chains along the c-axis direction which are further interlinked by the halogen bonds into layers parallel to the bc plane.
CCDC reference: 1001457
Related literature
For background to this study, see: Ishikawa & Fujii (2011). For a related structure, see: Ishikawa & Yoshida (2014).
Experimental
Crystal data
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Data collection: WinAFC Diffractometer Control Software (Rigaku, 1999); cell WinAFC Diffractometer Control Software; data reduction: WinAFC Diffractometer Control Software; program(s) used to solve structure: SIR2008 (Burla et al., 2007); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2010); software used to prepare material for publication: CrystalStructure.
Supporting information
CCDC reference: 1001457
10.1107/S1600536814010320/ld2125sup1.cif
contains datablocks General, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814010320/ld2125Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814010320/ld2125Isup3.cml
In a Schlenk tube under nitrogen atmosphere, the mixture of ethyl 7-chloro-4-oxo-1,4-dihydroquinoline-3-carboxylate (5.00 mmol), benzenesulfonyl chloride (5.00 mmol), K2CO3 (10.0 mmol) in 10 ml of DMF were stirred at 130 °C overnight. After cooling to room temperature ice water was added. The precipitates were collected, and were recrystallized from DMF to give white solids (yield: 18%). 1H NMR (400 MHz, DMSO-d6): δ = 0.90 (t, 3H, J = 7.0 Hz), 1.23 (t, 3H, J = 7.0 Hz), 4.03–4.15 (m, 2H), 4.20 (q, 2H, J = 7.0 Hz), 6.99 (d, 1H, J = 1.4 Hz), 7.52 (dd, 1H, J = 1.4 and 8.3 Hz), 7.74 (br s, 2H), 8.31 (d, 1H, J = 8.3 Hz), 8.43 (s, 1H), 8.70 (s, 1H), 9.57 (s, 1H). DART-MS calcd for [C24H18Cl2N2O5 + H+]: 484.059, found 485.099. Single crystals suitable for X-ray diffraction were obtained by slow evapolation of an ethyl acetate solution of the title compound at room temperature.
The C(sp2)-bound [C–H 0.95 Å, Uiso(H) = 1.2Ueq(C)] and methylene [C–H 0.99 Å, Uiso(H) = 1.2Ueq(C)] hydrogen atoms were placed in geometrical positions and refined using a riding model. A rotating group model was applied to the methyl groups with distance constraint [C–H = 0.98 Å, Uiso(H) = 1.2Ueq(C)].
Data collection: WinAFC Diffractometer Control Software (Rigaku, 1999); cell
WinAFC Diffractometer Control Software (Rigaku, 1999); data reduction: WinAFC Diffractometer Control Software (Rigaku, 1999); program(s) used to solve structure: SIR2008 (Burla et al., 2007); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2010); software used to prepare material for publication: CrystalStructure (Rigaku, 2010).C24H18Cl2N2O5 | Z = 2 |
Mr = 485.32 | F(000) = 500.00 |
Triclinic, P1 | Dx = 1.480 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71069 Å |
a = 7.631 (4) Å | Cell parameters from 25 reflections |
b = 12.416 (5) Å | θ = 15.3–17.4° |
c = 12.461 (5) Å | µ = 0.34 mm−1 |
α = 107.99 (3)° | T = 100 K |
β = 101.08 (3)° | Plate, colorless |
γ = 94.77 (3)° | 0.35 × 0.25 × 0.10 mm |
V = 1089.0 (8) Å3 |
Rigaku AFC-7R diffractometer | θmax = 27.5° |
ω–2θ scans | h = −9→9 |
6003 measured reflections | k = −15→16 |
4994 independent reflections | l = −16→9 |
4229 reflections with F2 > 2σ(F2) | 3 standard reflections every 150 reflections |
Rint = 0.059 | intensity decay: 1.7% |
Refinement on F2 | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.060 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.186 | H-atom parameters constrained |
S = 1.10 | w = 1/[σ2(Fo2) + (0.1156P)2 + 1.0113P] where P = (Fo2 + 2Fc2)/3 |
4994 reflections | (Δ/σ)max < 0.001 |
300 parameters | Δρmax = 0.66 e Å−3 |
0 restraints | Δρmin = −0.95 e Å−3 |
Primary atom site location: structure-invariant direct methods |
C24H18Cl2N2O5 | γ = 94.77 (3)° |
Mr = 485.32 | V = 1089.0 (8) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.631 (4) Å | Mo Kα radiation |
b = 12.416 (5) Å | µ = 0.34 mm−1 |
c = 12.461 (5) Å | T = 100 K |
α = 107.99 (3)° | 0.35 × 0.25 × 0.10 mm |
β = 101.08 (3)° |
Rigaku AFC-7R diffractometer | Rint = 0.059 |
6003 measured reflections | 3 standard reflections every 150 reflections |
4994 independent reflections | intensity decay: 1.7% |
4229 reflections with F2 > 2σ(F2) |
R[F2 > 2σ(F2)] = 0.060 | 0 restraints |
wR(F2) = 0.186 | H-atom parameters constrained |
S = 1.10 | Δρmax = 0.66 e Å−3 |
4994 reflections | Δρmin = −0.95 e Å−3 |
300 parameters |
Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt). |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.73301 (8) | 0.03469 (5) | 0.79333 (5) | 0.02074 (18) | |
Cl2 | −0.29884 (8) | 0.05407 (6) | 0.46908 (5) | 0.02351 (19) | |
O1 | 0.7561 (3) | 0.59358 (16) | 1.06621 (15) | 0.0228 (4) | |
O2 | 0.4484 (3) | 0.72976 (15) | 0.83028 (15) | 0.0197 (4) | |
O3 | 0.6483 (3) | 0.77390 (15) | 1.00077 (15) | 0.0198 (4) | |
O4 | 0.7338 (3) | 0.44766 (18) | 0.47536 (16) | 0.0261 (5) | |
O5 | 0.8082 (3) | 0.41909 (16) | 0.64744 (15) | 0.0182 (4) | |
N1 | 0.5095 (3) | 0.39265 (17) | 0.73369 (16) | 0.0138 (4) | |
N2 | 0.2732 (3) | 0.20828 (18) | 0.37892 (17) | 0.0174 (5) | |
C1 | 0.5012 (3) | 0.5061 (2) | 0.7706 (2) | 0.0141 (5) | |
C2 | 0.5822 (3) | 0.5797 (2) | 0.8794 (2) | 0.0145 (5) | |
C3 | 0.6857 (4) | 0.5365 (2) | 0.9646 (2) | 0.0163 (5) | |
C4 | 0.8031 (4) | 0.3633 (3) | 0.9917 (2) | 0.0198 (5) | |
C5 | 0.8157 (4) | 0.2478 (3) | 0.9544 (3) | 0.0208 (5) | |
C6 | 0.7215 (4) | 0.1800 (2) | 0.8429 (2) | 0.0175 (5) | |
C7 | 0.6192 (3) | 0.2257 (2) | 0.7685 (2) | 0.0157 (5) | |
C8 | 0.6992 (3) | 0.4127 (2) | 0.9191 (2) | 0.0154 (5) | |
C9 | 0.6093 (3) | 0.3430 (2) | 0.80736 (19) | 0.0142 (5) | |
C10 | 0.5507 (4) | 0.6999 (2) | 0.8995 (2) | 0.0152 (5) | |
C11 | 0.6218 (4) | 0.8920 (2) | 1.0198 (3) | 0.0202 (5) | |
C12 | 0.7347 (4) | 0.9628 (3) | 1.1383 (3) | 0.0272 (6) | |
C13 | 0.4320 (4) | 0.2725 (3) | 0.4112 (2) | 0.0178 (5) | |
C14 | 0.5195 (4) | 0.3360 (2) | 0.5282 (2) | 0.0157 (5) | |
C15 | 0.4338 (3) | 0.32682 (19) | 0.61337 (19) | 0.0141 (5) | |
C16 | 0.1675 (4) | 0.2425 (3) | 0.6666 (2) | 0.0179 (5) | |
C17 | −0.0004 (4) | 0.1789 (3) | 0.6309 (3) | 0.0193 (5) | |
C18 | −0.0794 (4) | 0.1281 (3) | 0.5107 (3) | 0.0190 (5) | |
C19 | 0.0106 (4) | 0.1366 (2) | 0.4280 (2) | 0.0185 (5) | |
C20 | 0.2636 (4) | 0.2570 (2) | 0.5836 (2) | 0.0158 (5) | |
C21 | 0.1866 (4) | 0.2007 (2) | 0.4634 (2) | 0.0156 (5) | |
C22 | 0.6974 (4) | 0.4081 (2) | 0.5471 (2) | 0.0171 (5) | |
C23 | 0.9888 (4) | 0.4845 (3) | 0.6723 (3) | 0.0203 (5) | |
C24 | 0.9854 (4) | 0.6121 (3) | 0.7135 (3) | 0.0259 (6) | |
H1 | 0.4346 | 0.5369 | 0.7175 | 0.0170* | |
H2 | 0.8658 | 0.4101 | 1.0677 | 0.0238* | |
H3 | 0.8873 | 0.2151 | 1.0037 | 0.0250* | |
H4 | 0.5570 | 0.1784 | 0.6926 | 0.0188* | |
H5A | 0.4926 | 0.8991 | 1.0160 | 0.0243* | |
H6B | 0.6599 | 0.9189 | 0.9596 | 0.0243* | |
H7A | 0.6963 | 0.9352 | 1.1971 | 0.0326* | |
H8B | 0.7188 | 1.0433 | 1.1540 | 0.0326* | |
H9C | 0.8623 | 0.9559 | 1.1408 | 0.0326* | |
H10 | 0.4926 | 0.2769 | 0.3525 | 0.0213* | |
H11 | 0.2205 | 0.2771 | 0.7470 | 0.0215* | |
H12 | −0.0642 | 0.1687 | 0.6863 | 0.0232* | |
H13 | −0.0441 | 0.1001 | 0.3480 | 0.0222* | |
H14A | 1.0365 | 0.4633 | 0.6013 | 0.0244* | |
H15B | 1.0710 | 0.4644 | 0.7325 | 0.0244* | |
H16A | 1.1094 | 0.6531 | 0.7397 | 0.0310* | |
H17B | 0.9245 | 0.6318 | 0.7779 | 0.0310* | |
H18C | 0.9200 | 0.6340 | 0.6497 | 0.0310* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0250 (4) | 0.0193 (3) | 0.0227 (4) | 0.0070 (3) | 0.0079 (3) | 0.0114 (3) |
Cl2 | 0.0156 (3) | 0.0274 (4) | 0.0264 (4) | −0.0013 (3) | 0.0043 (3) | 0.0089 (3) |
O1 | 0.0318 (11) | 0.0220 (10) | 0.0129 (9) | 0.0056 (8) | 0.0014 (7) | 0.0052 (7) |
O2 | 0.0249 (9) | 0.0203 (9) | 0.0161 (9) | 0.0049 (7) | 0.0034 (7) | 0.0094 (7) |
O3 | 0.0249 (10) | 0.0147 (9) | 0.0170 (9) | 0.0023 (7) | −0.0005 (7) | 0.0045 (7) |
O4 | 0.0241 (10) | 0.0375 (12) | 0.0205 (10) | −0.0052 (8) | 0.0041 (8) | 0.0181 (9) |
O5 | 0.0144 (8) | 0.0252 (9) | 0.0180 (9) | 0.0003 (7) | 0.0028 (7) | 0.0126 (7) |
N1 | 0.0160 (10) | 0.0165 (10) | 0.0101 (9) | 0.0026 (8) | 0.0030 (7) | 0.0063 (8) |
N2 | 0.0204 (10) | 0.0194 (10) | 0.0140 (10) | 0.0037 (8) | 0.0043 (8) | 0.0073 (8) |
C1 | 0.0155 (11) | 0.0163 (11) | 0.0130 (10) | 0.0012 (9) | 0.0054 (8) | 0.0074 (9) |
C2 | 0.0164 (11) | 0.0154 (11) | 0.0140 (11) | 0.0022 (9) | 0.0059 (9) | 0.0067 (9) |
C3 | 0.0183 (11) | 0.0196 (12) | 0.0133 (11) | 0.0029 (9) | 0.0067 (9) | 0.0069 (9) |
C4 | 0.0227 (12) | 0.0239 (13) | 0.0145 (11) | 0.0044 (10) | 0.0036 (9) | 0.0087 (10) |
C5 | 0.0243 (13) | 0.0254 (13) | 0.0182 (12) | 0.0092 (10) | 0.0053 (10) | 0.0134 (10) |
C6 | 0.0194 (12) | 0.0187 (12) | 0.0188 (12) | 0.0059 (9) | 0.0085 (9) | 0.0092 (10) |
C7 | 0.0164 (11) | 0.0190 (12) | 0.0149 (11) | 0.0036 (9) | 0.0062 (9) | 0.0083 (9) |
C8 | 0.0154 (11) | 0.0201 (12) | 0.0126 (11) | 0.0019 (9) | 0.0047 (9) | 0.0076 (9) |
C9 | 0.0145 (11) | 0.0201 (12) | 0.0126 (11) | 0.0036 (9) | 0.0065 (8) | 0.0096 (9) |
C10 | 0.0177 (11) | 0.0172 (11) | 0.0128 (11) | 0.0023 (9) | 0.0065 (9) | 0.0060 (9) |
C11 | 0.0263 (13) | 0.0153 (12) | 0.0188 (12) | 0.0034 (10) | 0.0033 (10) | 0.0065 (9) |
C12 | 0.0307 (15) | 0.0186 (13) | 0.0255 (14) | 0.0033 (11) | −0.0024 (11) | 0.0032 (11) |
C13 | 0.0185 (12) | 0.0234 (12) | 0.0157 (11) | 0.0038 (9) | 0.0064 (9) | 0.0108 (10) |
C14 | 0.0170 (11) | 0.0180 (11) | 0.0153 (11) | 0.0039 (9) | 0.0040 (9) | 0.0094 (9) |
C15 | 0.0166 (11) | 0.0151 (11) | 0.0126 (11) | 0.0044 (9) | 0.0024 (8) | 0.0074 (9) |
C16 | 0.0194 (12) | 0.0224 (12) | 0.0156 (11) | 0.0042 (9) | 0.0049 (9) | 0.0106 (10) |
C17 | 0.0191 (12) | 0.0249 (13) | 0.0190 (12) | 0.0058 (10) | 0.0085 (9) | 0.0114 (10) |
C18 | 0.0134 (11) | 0.0220 (12) | 0.0233 (13) | 0.0011 (9) | 0.0032 (9) | 0.0108 (10) |
C19 | 0.0182 (12) | 0.0211 (12) | 0.0170 (12) | 0.0028 (9) | 0.0023 (9) | 0.0085 (10) |
C20 | 0.0174 (11) | 0.0193 (12) | 0.0143 (11) | 0.0052 (9) | 0.0043 (9) | 0.0098 (9) |
C21 | 0.0162 (11) | 0.0167 (11) | 0.0154 (11) | 0.0023 (9) | 0.0016 (9) | 0.0086 (9) |
C22 | 0.0177 (11) | 0.0199 (12) | 0.0157 (11) | 0.0019 (9) | 0.0055 (9) | 0.0078 (9) |
C23 | 0.0128 (11) | 0.0272 (13) | 0.0233 (13) | 0.0010 (9) | 0.0032 (9) | 0.0126 (11) |
C24 | 0.0223 (13) | 0.0239 (14) | 0.0322 (15) | 0.0027 (10) | 0.0006 (11) | 0.0141 (12) |
Cl1—C6 | 1.733 (3) | C14—C22 | 1.498 (4) |
Cl2—C18 | 1.742 (3) | C15—C20 | 1.416 (4) |
O1—C3 | 1.231 (3) | C16—C17 | 1.364 (4) |
O2—C10 | 1.216 (4) | C16—C20 | 1.423 (4) |
O3—C10 | 1.341 (3) | C17—C18 | 1.418 (4) |
O3—C11 | 1.450 (4) | C18—C19 | 1.368 (5) |
O4—C22 | 1.209 (4) | C19—C21 | 1.418 (4) |
O5—C22 | 1.329 (3) | C20—C21 | 1.422 (3) |
O5—C23 | 1.466 (3) | C23—C24 | 1.511 (4) |
N1—C1 | 1.351 (4) | C1—H1 | 0.950 |
N1—C9 | 1.400 (4) | C4—H2 | 0.950 |
N1—C15 | 1.443 (3) | C5—H3 | 0.950 |
N2—C13 | 1.311 (4) | C7—H4 | 0.950 |
N2—C21 | 1.368 (4) | C11—H5A | 0.990 |
C1—C2 | 1.369 (3) | C11—H6B | 0.990 |
C2—C3 | 1.462 (4) | C12—H7A | 0.980 |
C2—C10 | 1.483 (4) | C12—H8B | 0.980 |
C3—C8 | 1.484 (4) | C12—H9C | 0.980 |
C4—C5 | 1.383 (4) | C13—H10 | 0.950 |
C4—C8 | 1.404 (4) | C16—H11 | 0.950 |
C5—C6 | 1.396 (4) | C17—H12 | 0.950 |
C6—C7 | 1.382 (4) | C19—H13 | 0.950 |
C7—C9 | 1.400 (4) | C23—H14A | 0.990 |
C8—C9 | 1.396 (3) | C23—H15B | 0.990 |
C11—C12 | 1.510 (4) | C24—H16A | 0.980 |
C13—C14 | 1.421 (3) | C24—H17B | 0.980 |
C14—C15 | 1.377 (4) | C24—H18C | 0.980 |
O1···O3 | 2.744 (3) | N1···H15Bv | 3.5315 |
O1···C1 | 3.599 (4) | N2···H17Biv | 3.4348 |
O1···C4 | 2.797 (4) | N2···H18Civ | 2.6158 |
O1···C10 | 3.050 (4) | C1···H10iv | 3.4894 |
O2···C1 | 2.730 (4) | C1···H15Bv | 3.1990 |
O2···C11 | 2.608 (3) | C3···H2xi | 3.5544 |
O3···C1 | 3.576 (3) | C3···H11iii | 3.5186 |
O3···C3 | 2.889 (4) | C4···H15Bxi | 3.3403 |
O4···C13 | 2.839 (4) | C4···H16Axi | 3.3578 |
O4···C23 | 2.710 (4) | C4···H17Bxi | 3.1853 |
O4···C24 | 3.174 (4) | C5···H5Aiii | 3.0056 |
O5···N1 | 2.737 (3) | C5···H12vii | 3.5018 |
O5···C1 | 3.129 (4) | C5···H16Axi | 3.5386 |
O5···C7 | 3.552 (4) | C5···H17Bxi | 3.3435 |
O5···C9 | 3.042 (4) | C6···H5Aiii | 2.9375 |
O5···C13 | 3.577 (4) | C6···H7Aiii | 3.2632 |
O5···C15 | 2.888 (4) | C6···H12vii | 2.7567 |
N1···C3 | 2.866 (3) | C7···H7Aiii | 3.1775 |
N1···C16 | 2.894 (4) | C7···H12vii | 2.8588 |
N1···C22 | 3.002 (4) | C10···H2iii | 3.5006 |
N2···C15 | 2.806 (3) | C10···H10iv | 3.1987 |
C1···C8 | 2.756 (4) | C10···H16Av | 3.4673 |
C1···C14 | 3.143 (4) | C11···H5Aviii | 2.9378 |
C1···C20 | 3.358 (4) | C11···H6Bviii | 3.2975 |
C1···C22 | 3.360 (4) | C11···H8Bviii | 3.3685 |
C2···C9 | 2.833 (4) | C12···H5Aviii | 3.3011 |
C4···C7 | 2.791 (4) | C12···H13xiii | 2.7669 |
C5···C9 | 2.788 (4) | C13···H1iv | 3.4318 |
C6···C8 | 2.780 (4) | C13···H18Civ | 3.0680 |
C7···C15 | 2.839 (4) | C15···H14Av | 3.5947 |
C7···C16 | 3.484 (4) | C16···H7Aiii | 3.2940 |
C7···C20 | 3.339 (4) | C16···H14Av | 3.2712 |
C9···C14 | 3.386 (4) | C16···H15Bv | 2.8250 |
C9···C16 | 3.417 (4) | C17···H7Aiii | 3.5354 |
C9···C20 | 3.277 (4) | C17···H13ix | 3.5923 |
C13···C19 | 3.578 (4) | C17···H15Bv | 3.3327 |
C13···C20 | 2.752 (5) | C19···H7Axii | 3.4912 |
C14···C21 | 2.755 (4) | C19···H8Bxii | 3.4869 |
C16···C19 | 2.821 (4) | C19···H9Cxii | 3.4902 |
C17···C21 | 2.809 (5) | C19···H18Civ | 3.3135 |
C18···C20 | 2.780 (4) | C20···H14Av | 3.1857 |
C22···C24 | 3.102 (4) | C20···H15Bv | 3.3105 |
Cl1···N2i | 3.106 (3) | C21···H14Av | 3.5795 |
Cl2···Cl2ii | 3.5616 (17) | C21···H18Civ | 2.9127 |
O1···N1iii | 3.477 (4) | C22···H1iv | 3.5465 |
O1···C1iii | 3.494 (4) | C22···H14Avi | 3.5804 |
O1···C2iii | 3.521 (4) | C23···H1vii | 3.3137 |
O1···C3iii | 3.512 (4) | C23···H2xi | 3.0336 |
O1···C8iii | 3.509 (4) | C23···H11vii | 3.4964 |
O1···C9iii | 3.487 (4) | C24···H2xi | 2.8503 |
O1···C16iii | 3.231 (3) | C24···H3xi | 3.4109 |
O2···C4iii | 3.577 (4) | H1···O4iv | 2.5687 |
O2···C13iv | 3.301 (4) | H1···C13iv | 3.4318 |
O2···C24v | 3.548 (4) | H1···C22iv | 3.5465 |
O4···C1iv | 3.476 (4) | H1···C23v | 3.3137 |
O4···C14iv | 3.443 (4) | H1···H10iv | 2.7626 |
O4···C15iv | 3.558 (4) | H1···H14Av | 3.0313 |
O4···C23vi | 3.276 (4) | H1···H15Bv | 2.9039 |
O4···C24vi | 3.436 (4) | H1···H16Av | 2.9874 |
O5···C17vii | 3.395 (4) | H2···O1xi | 3.5966 |
N1···O1iii | 3.477 (4) | H2···O2iii | 3.4958 |
N2···Cl1i | 3.106 (3) | H2···C3xi | 3.5544 |
N2···C24iv | 3.412 (4) | H2···C10iii | 3.5006 |
C1···O1iii | 3.494 (4) | H2···C23xi | 3.0336 |
C1···O4iv | 3.476 (4) | H2···C24xi | 2.8503 |
C2···O1iii | 3.521 (4) | H2···H15Bxi | 2.4244 |
C2···C3iii | 3.578 (5) | H2···H16Axi | 2.7246 |
C2···C8iii | 3.589 (4) | H2···H17Bxi | 2.4712 |
C3···O1iii | 3.512 (4) | H3···O2iii | 3.5724 |
C3···C2iii | 3.578 (5) | H3···O3xi | 3.5471 |
C3···C3iii | 3.264 (4) | H3···C24xi | 3.4109 |
C3···C8iii | 3.535 (4) | H3···H5Aiii | 3.0498 |
C4···O2iii | 3.577 (4) | H3···H8Bx | 3.5569 |
C4···C10iii | 3.384 (5) | H3···H9Cxi | 3.3216 |
C6···C11iii | 3.587 (5) | H3···H16Axi | 3.1037 |
C8···O1iii | 3.509 (4) | H3···H17Bxi | 2.8161 |
C8···C2iii | 3.589 (4) | H4···Cl2vii | 3.1862 |
C8···C3iii | 3.535 (4) | H4···Cl2ix | 3.1952 |
C9···O1iii | 3.487 (4) | H4···H7Aiii | 3.0634 |
C10···C4iii | 3.384 (5) | H4···H12vii | 2.9178 |
C11···C6iii | 3.587 (5) | H5A···Cl1iii | 3.1443 |
C11···C11viii | 3.490 (5) | H5A···C5iii | 3.0056 |
C13···O2iv | 3.301 (4) | H5A···C6iii | 2.9375 |
C14···O4iv | 3.443 (4) | H5A···C11viii | 2.9378 |
C15···O4iv | 3.558 (4) | H5A···C12viii | 3.3011 |
C16···O1iii | 3.231 (3) | H5A···H3iii | 3.0498 |
C16···C23v | 3.388 (5) | H5A···H5Aviii | 2.6538 |
C17···O5v | 3.395 (4) | H5A···H6Bviii | 2.5893 |
C18···C18ix | 3.450 (4) | H5A···H8Bviii | 2.7235 |
C23···O4vi | 3.276 (4) | H6B···Cl1xiv | 2.9705 |
C23···C16vii | 3.388 (5) | H6B···C11viii | 3.2975 |
C24···O2vii | 3.548 (4) | H6B···H5Aviii | 2.5893 |
C24···O4vi | 3.436 (4) | H6B···H6Bviii | 3.3956 |
C24···N2iv | 3.412 (4) | H6B···H8Bviii | 3.1042 |
Cl1···H3 | 2.8323 | H7A···Cl1iii | 3.3484 |
Cl1···H4 | 2.7746 | H7A···Cl2xiii | 3.2436 |
Cl2···H12 | 2.8089 | H7A···C6iii | 3.2632 |
Cl2···H13 | 2.8031 | H7A···C7iii | 3.1775 |
O1···H2 | 2.4958 | H7A···C16iii | 3.2940 |
O2···H1 | 2.3541 | H7A···C17iii | 3.5354 |
O2···H5A | 2.5424 | H7A···C19xiii | 3.4912 |
O2···H6B | 2.5978 | H7A···H4iii | 3.0634 |
O3···H7A | 2.5759 | H7A···H11iii | 3.0133 |
O3···H8B | 3.2380 | H7A···H12iii | 3.4423 |
O3···H9C | 2.5830 | H7A···H13xiii | 2.6772 |
O4···H10 | 2.5478 | H8B···O2viii | 3.1553 |
O4···H14A | 2.4861 | H8B···C11viii | 3.3685 |
O4···H18C | 2.6932 | H8B···C19xiii | 3.4869 |
O5···H1 | 3.4480 | H8B···H3xiv | 3.5569 |
O5···H16A | 3.2950 | H8B···H5Aviii | 2.7235 |
O5···H17B | 2.6098 | H8B···H6Bviii | 3.1042 |
O5···H18C | 2.7231 | H8B···H13xiii | 2.5821 |
N1···H4 | 2.6190 | H9C···Cl1xi | 3.0218 |
N1···H11 | 2.5903 | H9C···C19xiii | 3.4902 |
N2···H13 | 2.5685 | H9C···H3xi | 3.3216 |
C1···H11 | 3.3147 | H9C···H12iii | 3.2541 |
C1···H17B | 3.4411 | H9C···H13xiii | 2.5698 |
C2···H17B | 3.2151 | H10···O2iv | 2.3840 |
C3···H1 | 3.3018 | H10···C1iv | 3.4894 |
C3···H2 | 2.6316 | H10···C10iv | 3.1987 |
C5···H4 | 3.2843 | H10···H1iv | 2.7626 |
C6···H2 | 3.2504 | H10···H16Avi | 3.5807 |
C7···H3 | 3.2817 | H10···H18Civ | 3.4202 |
C7···H11 | 3.1390 | H11···O1iii | 2.3474 |
C8···H3 | 3.2855 | H11···O3iii | 3.3776 |
C8···H4 | 3.2917 | H11···C3iii | 3.5186 |
C9···H1 | 3.2331 | H11···C23v | 3.4964 |
C9···H2 | 3.2661 | H11···H7Aiii | 3.0133 |
C9···H11 | 2.8974 | H11···H14Av | 3.5728 |
C10···H1 | 2.4741 | H11···H15Bv | 2.7129 |
C10···H5A | 2.5743 | H12···Cl1v | 2.9460 |
C10···H6B | 2.6022 | H12···O5v | 3.4785 |
C10···H17B | 3.5241 | H12···C5v | 3.5018 |
C14···H1 | 3.0701 | H12···C6v | 2.7567 |
C14···H4 | 3.2328 | H12···C7v | 2.8588 |
C15···H1 | 2.5282 | H12···H4v | 2.9178 |
C15···H4 | 2.5115 | H12···H7Aiii | 3.4423 |
C15···H10 | 3.2423 | H12···H9Ciii | 3.2541 |
C15···H11 | 2.7043 | H12···H13ix | 3.4222 |
C16···H4 | 3.1231 | H12···H15Bv | 3.5653 |
C17···H13 | 3.2952 | H13···Cl1i | 3.4612 |
C18···H11 | 3.2670 | H13···C12xii | 2.7669 |
C19···H12 | 3.2857 | H13···C17ix | 3.5923 |
C20···H1 | 3.3755 | H13···H7Axii | 2.6772 |
C20···H4 | 2.7971 | H13···H8Bxii | 2.5821 |
C20···H12 | 3.2767 | H13···H9Cxii | 2.5698 |
C20···H13 | 3.3143 | H13···H12ix | 3.4222 |
C21···H10 | 3.1520 | H13···H16Aiv | 3.5989 |
C21···H11 | 3.3155 | H13···H18Civ | 3.3482 |
C22···H1 | 3.3402 | H14A···O4vi | 2.4859 |
C22···H10 | 2.5803 | H14A···C15vii | 3.5947 |
C22···H14A | 2.5239 | H14A···C16vii | 3.2712 |
C22···H15B | 3.1771 | H14A···C20vii | 3.1857 |
C22···H17B | 3.3676 | H14A···C21vii | 3.5795 |
C22···H18C | 2.9232 | H14A···C22vi | 3.5804 |
H2···H3 | 2.3340 | H14A···H1vii | 3.0313 |
H4···H11 | 3.0391 | H14A···H11vii | 3.5728 |
H5A···H7A | 2.3705 | H14A···H14Avi | 2.9112 |
H5A···H8B | 2.3637 | H14A···H18Cvi | 3.0792 |
H5A···H9C | 2.8598 | H15B···O1xi | 2.9240 |
H6B···H7A | 2.8598 | H15B···N1vii | 3.5315 |
H6B···H8B | 2.3689 | H15B···C1vii | 3.1990 |
H6B···H9C | 2.3653 | H15B···C4xi | 3.3403 |
H11···H12 | 2.3146 | H15B···C16vii | 2.8250 |
H14A···H16A | 2.3955 | H15B···C17vii | 3.3327 |
H14A···H17B | 2.8510 | H15B···C20vii | 3.3105 |
H14A···H18C | 2.3186 | H15B···H1vii | 2.9039 |
H15B···H16A | 2.3082 | H15B···H2xi | 2.4244 |
H15B···H17B | 2.4072 | H15B···H11vii | 2.7129 |
H15B···H18C | 2.8493 | H15B···H12vii | 3.5653 |
Cl1···H5Aiii | 3.1443 | H16A···O2vii | 2.5834 |
Cl1···H6Bx | 2.9705 | H16A···O4vi | 3.0967 |
Cl1···H7Aiii | 3.3484 | H16A···C4xi | 3.3578 |
Cl1···H9Cxi | 3.0218 | H16A···C5xi | 3.5386 |
Cl1···H12vii | 2.9460 | H16A···C10vii | 3.4673 |
Cl1···H13i | 3.4612 | H16A···H1vii | 2.9874 |
Cl2···H4v | 3.1862 | H16A···H2xi | 2.7246 |
Cl2···H4ix | 3.1952 | H16A···H3xi | 3.1037 |
Cl2···H7Axii | 3.2436 | H16A···H10vi | 3.5807 |
O1···H2xi | 3.5966 | H16A···H13iv | 3.5989 |
O1···H11iii | 2.3474 | H17B···N2iv | 3.4348 |
O1···H15Bxi | 2.9240 | H17B···C4xi | 3.1853 |
O2···H2iii | 3.4958 | H17B···C5xi | 3.3435 |
O2···H3iii | 3.5724 | H17B···H2xi | 2.4712 |
O2···H8Bviii | 3.1553 | H17B···H3xi | 2.8161 |
O2···H10iv | 2.3840 | H18C···O4vi | 3.3897 |
O2···H16Av | 2.5834 | H18C···N2iv | 2.6158 |
O3···H3xi | 3.5471 | H18C···C13iv | 3.0680 |
O3···H11iii | 3.3776 | H18C···C19iv | 3.3135 |
O4···H1iv | 2.5687 | H18C···C21iv | 2.9127 |
O4···H14Avi | 2.4859 | H18C···H10iv | 3.4202 |
O4···H16Avi | 3.0967 | H18C···H13iv | 3.3482 |
O4···H18Cvi | 3.3897 | H18C···H14Avi | 3.0792 |
O5···H12vii | 3.4785 | ||
C10—O3—C11 | 114.2 (2) | N2—C21—C19 | 117.8 (2) |
C22—O5—C23 | 116.9 (3) | N2—C21—C20 | 122.8 (2) |
C1—N1—C9 | 120.29 (18) | C19—C21—C20 | 119.4 (3) |
C1—N1—C15 | 118.8 (3) | O4—C22—O5 | 125.3 (3) |
C9—N1—C15 | 120.4 (2) | O4—C22—C14 | 122.1 (3) |
C13—N2—C21 | 117.9 (2) | O5—C22—C14 | 112.7 (3) |
N1—C1—C2 | 124.4 (3) | O5—C23—C24 | 111.6 (3) |
C1—C2—C3 | 119.9 (3) | N1—C1—H1 | 117.786 |
C1—C2—C10 | 114.2 (3) | C2—C1—H1 | 117.790 |
C3—C2—C10 | 125.88 (19) | C5—C4—H2 | 119.465 |
O1—C3—C2 | 125.3 (3) | C8—C4—H2 | 119.451 |
O1—C3—C8 | 120.6 (3) | C4—C5—H3 | 120.608 |
C2—C3—C8 | 114.06 (19) | C6—C5—H3 | 120.608 |
C5—C4—C8 | 121.1 (2) | C6—C7—H4 | 120.721 |
C4—C5—C6 | 118.8 (3) | C9—C7—H4 | 120.707 |
Cl1—C6—C5 | 120.1 (3) | O3—C11—H5A | 110.202 |
Cl1—C6—C7 | 118.02 (17) | O3—C11—H6B | 110.200 |
C5—C6—C7 | 121.9 (3) | C12—C11—H5A | 110.211 |
C6—C7—C9 | 118.6 (2) | C12—C11—H6B | 110.205 |
C3—C8—C4 | 118.94 (19) | H5A—C11—H6B | 108.490 |
C3—C8—C9 | 122.3 (3) | C11—C12—H7A | 109.471 |
C4—C8—C9 | 118.7 (3) | C11—C12—H8B | 109.470 |
N1—C9—C7 | 120.18 (19) | C11—C12—H9C | 109.479 |
N1—C9—C8 | 118.8 (3) | H7A—C12—H8B | 109.465 |
C7—C9—C8 | 121.0 (3) | H7A—C12—H9C | 109.468 |
O2—C10—O3 | 122.7 (3) | H8B—C12—H9C | 109.475 |
O2—C10—C2 | 123.53 (19) | N2—C13—H10 | 117.798 |
O3—C10—C2 | 113.8 (3) | C14—C13—H10 | 117.799 |
O3—C11—C12 | 107.5 (3) | C17—C16—H11 | 119.933 |
N2—C13—C14 | 124.4 (3) | C20—C16—H11 | 119.934 |
C13—C14—C15 | 117.7 (3) | C16—C17—H12 | 120.148 |
C13—C14—C22 | 116.4 (3) | C18—C17—H12 | 120.160 |
C15—C14—C22 | 125.9 (2) | C18—C19—H13 | 120.507 |
N1—C15—C14 | 121.1 (2) | C21—C19—H13 | 120.503 |
N1—C15—C20 | 118.5 (3) | O5—C23—H14A | 109.305 |
C14—C15—C20 | 120.3 (2) | O5—C23—H15B | 109.313 |
C17—C16—C20 | 120.1 (3) | C24—C23—H14A | 109.316 |
C16—C17—C18 | 119.7 (3) | C24—C23—H15B | 109.312 |
Cl2—C18—C17 | 118.1 (3) | H14A—C23—H15B | 107.959 |
Cl2—C18—C19 | 119.79 (18) | C23—C24—H16A | 109.468 |
C17—C18—C19 | 122.1 (3) | C23—C24—H17B | 109.468 |
C18—C19—C21 | 119.0 (2) | C23—C24—H18C | 109.468 |
C15—C20—C16 | 123.6 (2) | H16A—C24—H17B | 109.471 |
C15—C20—C21 | 116.9 (3) | H16A—C24—H18C | 109.475 |
C16—C20—C21 | 119.5 (2) | H17B—C24—H18C | 109.478 |
C10—O3—C11—C12 | 177.9 (2) | C3—C8—C9—N1 | 3.0 (4) |
C10—O3—C11—H5A | 57.8 | C3—C8—C9—C7 | −177.6 (3) |
C10—O3—C11—H6B | −61.9 | C4—C8—C9—N1 | −178.3 (3) |
C11—O3—C10—O2 | −0.4 (4) | C4—C8—C9—C7 | 1.1 (4) |
C11—O3—C10—C2 | 178.5 (2) | O3—C11—C12—H7A | −59.5 |
C22—O5—C23—C24 | 79.0 (3) | O3—C11—C12—H8B | −179.5 |
C22—O5—C23—H14A | −42.1 | O3—C11—C12—H9C | 60.5 |
C22—O5—C23—H15B | −160.0 | H5A—C11—C12—H7A | 60.6 |
C23—O5—C22—O4 | −0.1 (4) | H5A—C11—C12—H8B | −59.4 |
C23—O5—C22—C14 | 177.69 (18) | H5A—C11—C12—H9C | −179.4 |
C1—N1—C9—C7 | −179.3 (2) | H6B—C11—C12—H7A | −179.7 |
C1—N1—C9—C8 | 0.1 (4) | H6B—C11—C12—H8B | 60.3 |
C9—N1—C1—C2 | −1.5 (4) | H6B—C11—C12—H9C | −59.7 |
C9—N1—C1—H1 | 178.5 | N2—C13—C14—C15 | 1.9 (4) |
C1—N1—C15—C14 | 73.6 (3) | N2—C13—C14—C22 | −177.6 (3) |
C1—N1—C15—C20 | −102.8 (3) | H10—C13—C14—C15 | −178.1 |
C15—N1—C1—C2 | −173.7 (2) | H10—C13—C14—C22 | 2.4 |
C15—N1—C1—H1 | 6.3 | C13—C14—C15—N1 | −177.0 (2) |
C9—N1—C15—C14 | −98.5 (3) | C13—C14—C15—C20 | −0.7 (4) |
C9—N1—C15—C20 | 85.0 (3) | C13—C14—C22—O4 | 28.4 (4) |
C15—N1—C9—C7 | −7.3 (4) | C13—C14—C22—O5 | −149.5 (3) |
C15—N1—C9—C8 | 172.1 (2) | C15—C14—C22—O4 | −151.1 (3) |
C13—N2—C21—C19 | 176.4 (3) | C15—C14—C22—O5 | 31.0 (4) |
C13—N2—C21—C20 | −1.5 (4) | C22—C14—C15—N1 | 2.5 (4) |
C21—N2—C13—C14 | −0.8 (4) | C22—C14—C15—C20 | 178.8 (3) |
C21—N2—C13—H10 | 179.2 | N1—C15—C20—C16 | −4.0 (4) |
N1—C1—C2—C3 | −0.2 (4) | N1—C15—C20—C21 | 175.0 (2) |
N1—C1—C2—C10 | −179.0 (2) | C14—C15—C20—C16 | 179.5 (3) |
H1—C1—C2—C3 | 179.8 | C14—C15—C20—C21 | −1.4 (4) |
H1—C1—C2—C10 | 1.0 | C17—C16—C20—C15 | 176.3 (3) |
C1—C2—C3—O1 | −176.1 (3) | C17—C16—C20—C21 | −2.7 (4) |
C1—C2—C3—C8 | 3.0 (4) | C20—C16—C17—C18 | −0.5 (4) |
C1—C2—C10—O2 | 6.7 (4) | C20—C16—C17—H12 | 179.5 |
C1—C2—C10—O3 | −172.1 (2) | H11—C16—C17—C18 | 179.5 |
C3—C2—C10—O2 | −172.0 (3) | H11—C16—C17—H12 | −0.5 |
C3—C2—C10—O3 | 9.1 (4) | H11—C16—C20—C15 | −3.7 |
C10—C2—C3—O1 | 2.5 (5) | H11—C16—C20—C21 | 177.3 |
C10—C2—C3—C8 | −178.3 (3) | C16—C17—C18—Cl2 | −176.6 (3) |
O1—C3—C8—C4 | −4.0 (4) | C16—C17—C18—C19 | 2.8 (5) |
O1—C3—C8—C9 | 174.8 (3) | H12—C17—C18—Cl2 | 3.4 |
C2—C3—C8—C4 | 176.8 (2) | H12—C17—C18—C19 | −177.2 |
C2—C3—C8—C9 | −4.5 (4) | Cl2—C18—C19—C21 | 177.74 (17) |
C5—C4—C8—C3 | 178.2 (3) | Cl2—C18—C19—H13 | −2.3 |
C5—C4—C8—C9 | −0.6 (4) | C17—C18—C19—C21 | −1.7 (4) |
C8—C4—C5—C6 | −0.6 (5) | C17—C18—C19—H13 | 178.3 |
C8—C4—C5—H3 | 179.4 | C18—C19—C21—N2 | −179.7 (3) |
H2—C4—C5—C6 | 179.4 | C18—C19—C21—C20 | −1.6 (4) |
H2—C4—C5—H3 | −0.6 | H13—C19—C21—N2 | 0.3 |
H2—C4—C8—C3 | −1.8 | H13—C19—C21—C20 | 178.4 |
H2—C4—C8—C9 | 179.4 | C15—C20—C21—N2 | 2.6 (4) |
C4—C5—C6—Cl1 | −179.6 (3) | C15—C20—C21—C19 | −175.3 (2) |
C4—C5—C6—C7 | 1.3 (5) | C16—C20—C21—N2 | −178.2 (3) |
H3—C5—C6—Cl1 | 0.3 | C16—C20—C21—C19 | 3.8 (4) |
H3—C5—C6—C7 | −178.7 | O5—C23—C24—H16A | 172.0 |
Cl1—C6—C7—C9 | −179.81 (17) | O5—C23—C24—H17B | 52.0 |
Cl1—C6—C7—H4 | 0.2 | O5—C23—C24—H18C | −68.0 |
C5—C6—C7—C9 | −0.7 (4) | H14A—C23—C24—H16A | −67.0 |
C5—C6—C7—H4 | 179.3 | H14A—C23—C24—H17B | 173.1 |
C6—C7—C9—N1 | 178.9 (3) | H14A—C23—C24—H18C | 53.0 |
C6—C7—C9—C8 | −0.5 (4) | H15B—C23—C24—H16A | 51.0 |
H4—C7—C9—N1 | −1.1 | H15B—C23—C24—H17B | −69.0 |
H4—C7—C9—C8 | 179.5 | H15B—C23—C24—H18C | 171.0 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x−1, −y, −z+1; (iii) −x+1, −y+1, −z+2; (iv) −x+1, −y+1, −z+1; (v) x−1, y, z; (vi) −x+2, −y+1, −z+1; (vii) x+1, y, z; (viii) −x+1, −y+2, −z+2; (ix) −x, −y, −z+1; (x) x, y−1, z; (xi) −x+2, −y+1, −z+2; (xii) x−1, y−1, z−1; (xiii) x+1, y+1, z+1; (xiv) x, y+1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C16—H11···O1iii | 0.95 | 2.35 | 3.231 (3) | 155 (1) |
C13—H10···O2iv | 0.95 | 2.38 | 3.301 (4) | 162 (1) |
Symmetry codes: (iii) −x+1, −y+1, −z+2; (iv) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C16—H11···O1i | 0.95 | 2.347 | 3.231 (3) | 154.60 (18) |
C13—H10···O2ii | 0.95 | 2.384 | 3.301 (4) | 162.26 (14) |
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x+1, −y+1, −z+1. |
Acknowledgements
This work was partly supported by Grants-in-Aid (No. 24590141 to YI) for Scientific Research from the Japan Society for the Promotion of Science. We acknowledge the University of Shizuoka for instrumental support.
References
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4-Quinolones show inhibition not only to Gram negative and Gram positive bacteria, but also to human immunodeficiency virus (HIV). The inhibition to HIV is derived from their chelating ability to metal ions in the active site of metalloenzyme HIV integrase. According to our inhibitor design targeting metalloenzyme influenza virus RNA polymerase (Ishikawa & Fujii, 2011), we tried to synthesize a 4-quinolone derivative bearing a benzenesulfonyl group. The crystallographic analysis revealed that the reaction of ethyl 4-oxo-1,4-dihydroquinoline-3-carboxylate with benzenesulfonyl chloride in the presence of K2CO3 in N,N-dimethylformamide (DMF) at 120 °C provided an unexpected 1,4'-biquinoline derivative, diethyl 4-oxo-4H-[1,4'-biquinoline]-3,3'-dicarboxylate (Ishikawa & Yoshida, 2014). 1,4'-Biquinoline derivatives might be potential enzyme inhibitors. Thus, we synthesized the title compound, a dichlorinated 1,4'-biquinoline derivative, by the similar method mentioned above, and herein report its crystal structure.
As shown in Fig.1, the C–N bond formation between the quinolinone and quinoline rings is confirmed. The chloroquinolinone and chloroquinoline moieties are nearly perpendicular to each other [dihedral angle = 97.64 (3)°]. In the crystal, the molecules are linked to each other to give dimers through halogen bond between the Cl atoms of the chloroquinolinone moieties and the N atoms of the chloroquinoline moieties of the inversion equivalentsi [Cl1···N2 = 3.106 (3) Å, i: –x + 1, –y, –z + 1]. Two systems of C–H···O hydrogen-bonded dimers form chains along the c-axis, which are interlinked by the halogen bonds forming layers parallel to the bc plane, as shown in Fig.2. On the other hand, clear-cut ring-ring stacking interaction is not found. These findings are in contrast with those in the crystal packing of diethyl 4-oxo-4H-[1,4'-biquinoline]-3,3'-dicarboxylate (Ishikawa & Yoshida, 2014).