organic compounds
Diethyl 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 molecule, C24H20N2O5, the quinoline and quinolinone moieties are practically perpendicular to each other, forming a dihedral angle of 89.06 (3)°. In the crystal, each moiety forms coplanar π-stacked couples with the respective inversion equivalents. The quinolinone moieties overlap with their benzene rings with a centroid–centroid separation of 3.641 (2) Å, whereas the quinoline moieties overlap with their pyridine rings with a separation of 3.592 (2) Å. The resulting supramolecular chains propargate along [101].
CCDC reference: 994976
Related literature
For the background to this study, see: Ishikawa & Fujii (2011). For a related compound, see: Kajihara (1965).
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: 994976
10.1107/S1600536814007314/ld2124sup1.cif
contains datablocks General, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814007314/ld2124Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814007314/ld2124Isup3.cml
In a Schlenk tube under nitrogen atmosphere, the mixture of ethyl 4-oxo-1,4-dihydroquinoline-3-carboxylate (0.20 g, 1.0 mmol), benzenesufonyl chloride (0.35 g, 2.0 mmol), K2CO3 (0.28 g, 2.0 mmol) in 5 ml of DMF were stirred at 120 °C overnight. After cooling to room temperature water was added, and the mixture was extracted with ethyl acetate three times. The extract was dried over anhydrous Na2SO4, and purified by δ = 0.87 (t, 3H, J = 7.1 Hz), 1.24 (t, 3H, J = 7.1 Hz), 4.07 (m, 2H), 4.21 (q, 2H, J = 7.1 Hz), 6.71 (d, 1H, J = 7.3 Hz), 7.50 (m, 2H), 7.60 (d, 1H, J = 8.3 Hz), 7.74 (t, 1H, J = 7.6 Hz), 8.05 (t, 1H, J = 7.8 Hz), 8.33 (d, 1H, J = 8.3 Hz), 8.34 (d, 1H, J = 8.3 Hz), 8.74 (s, 1H), 9.57 (s, 1H). DART-MS calcd for [C24H20N2O5 + H+]: 417.188, found 417.150. Single crystals suitable for X-ray diffraction were obtained by slow evapolation of an ethyl acetate solution of the title compound at room temperature.
on silica gel (ethyl acetate: ethanol = 180: 5, yield: 33%). 1H NMR (400 MHz, DMSO-d6):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).C24H20N2O5 | Z = 2 |
Mr = 416.43 | F(000) = 436.00 |
Triclinic, P1 | Dx = 1.421 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71069 Å |
a = 7.4478 (16) Å | Cell parameters from 25 reflections |
b = 11.284 (5) Å | θ = 15.3–17.3° |
c = 12.583 (5) Å | µ = 0.10 mm−1 |
α = 107.78 (3)° | T = 100 K |
β = 92.96 (3)° | Plate, colorless |
γ = 102.85 (3)° | 0.25 × 0.20 × 0.15 mm |
V = 973.5 (6) Å3 |
Rigaku AFC-7R diffractometer | θmax = 27.5° |
ω–2θ scans | h = −9→5 |
5486 measured reflections | k = −14→14 |
4479 independent reflections | l = −16→16 |
3077 reflections with F2 > 2σ(F2) | 3 standard reflections every 150 reflections |
Rint = 0.034 | intensity decay: −0.2% |
Refinement on F2 | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.159 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0934P)2 + 0.0738P] where P = (Fo2 + 2Fc2)/3 |
4479 reflections | (Δ/σ)max < 0.001 |
282 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.31 e Å−3 |
Primary atom site location: structure-invariant direct methods |
C24H20N2O5 | γ = 102.85 (3)° |
Mr = 416.43 | V = 973.5 (6) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.4478 (16) Å | Mo Kα radiation |
b = 11.284 (5) Å | µ = 0.10 mm−1 |
c = 12.583 (5) Å | T = 100 K |
α = 107.78 (3)° | 0.25 × 0.20 × 0.15 mm |
β = 92.96 (3)° |
Rigaku AFC-7R diffractometer | Rint = 0.034 |
5486 measured reflections | 3 standard reflections every 150 reflections |
4479 independent reflections | intensity decay: −0.2% |
3077 reflections with F2 > 2σ(F2) |
R[F2 > 2σ(F2)] = 0.052 | 0 restraints |
wR(F2) = 0.159 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.26 e Å−3 |
4479 reflections | Δρmin = −0.31 e Å−3 |
282 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 | ||
O1 | 0.3332 (2) | 0.32182 (13) | 0.08577 (12) | 0.0232 (4) | |
O2 | 0.80212 (19) | 0.33534 (14) | 0.30167 (12) | 0.0236 (4) | |
O3 | 0.69998 (19) | 0.40856 (13) | 0.16873 (12) | 0.0222 (4) | |
O4 | 0.1676 (2) | 0.17036 (14) | 0.61313 (12) | 0.0259 (4) | |
O5 | 0.2323 (2) | 0.24073 (13) | 0.46750 (12) | 0.0228 (4) | |
N1 | 0.3020 (2) | 0.08516 (14) | 0.27797 (13) | 0.0145 (4) | |
N2 | 0.2925 (3) | −0.17369 (16) | 0.46462 (14) | 0.0206 (4) | |
C1 | 0.4640 (3) | 0.16992 (17) | 0.28111 (15) | 0.0149 (4) | |
C2 | 0.4860 (3) | 0.25268 (17) | 0.21964 (15) | 0.0149 (4) | |
C3 | 0.3287 (3) | 0.25386 (17) | 0.14649 (15) | 0.0150 (4) | |
C4 | −0.0110 (3) | 0.15898 (18) | 0.08414 (16) | 0.0177 (4) | |
C5 | −0.1760 (3) | 0.07462 (19) | 0.08318 (16) | 0.0203 (4) | |
C6 | −0.1832 (3) | −0.00914 (19) | 0.14607 (16) | 0.0202 (5) | |
C7 | −0.0263 (3) | −0.00679 (18) | 0.21064 (16) | 0.0170 (4) | |
C8 | 0.1514 (3) | 0.16402 (17) | 0.14924 (15) | 0.0145 (4) | |
C9 | 0.1409 (3) | 0.08087 (17) | 0.21275 (15) | 0.0142 (4) | |
C10 | 0.6784 (3) | 0.33482 (17) | 0.23514 (16) | 0.0159 (4) | |
C11 | 0.8869 (3) | 0.48947 (19) | 0.17788 (18) | 0.0214 (5) | |
C12 | 0.8689 (3) | 0.5903 (2) | 0.1253 (2) | 0.0280 (5) | |
C13 | 0.2596 (3) | −0.06055 (19) | 0.50924 (17) | 0.0185 (4) | |
C14 | 0.2587 (3) | 0.03214 (18) | 0.45333 (16) | 0.0165 (4) | |
C15 | 0.2959 (3) | −0.00050 (17) | 0.34353 (16) | 0.0155 (4) | |
C16 | 0.3614 (3) | −0.16464 (18) | 0.17583 (16) | 0.0174 (4) | |
C17 | 0.3957 (3) | −0.28265 (19) | 0.12941 (17) | 0.0209 (5) | |
C18 | 0.3959 (3) | −0.36552 (19) | 0.19449 (18) | 0.0231 (5) | |
C19 | 0.3611 (3) | −0.32810 (19) | 0.30362 (18) | 0.0222 (5) | |
C20 | 0.3277 (3) | −0.12283 (17) | 0.28961 (16) | 0.0159 (4) | |
C21 | 0.3266 (3) | −0.20668 (18) | 0.35423 (16) | 0.0176 (4) | |
C22 | 0.2150 (3) | 0.15395 (18) | 0.52060 (16) | 0.0174 (4) | |
C23 | 0.1895 (3) | 0.36186 (19) | 0.52667 (18) | 0.0233 (5) | |
C24 | 0.2266 (3) | 0.44432 (19) | 0.45232 (18) | 0.0233 (5) | |
H1 | 0.5688 | 0.1723 | 0.3288 | 0.0179* | |
H2 | −0.0066 | 0.2145 | 0.0403 | 0.0212* | |
H3 | −0.2852 | 0.0731 | 0.0398 | 0.0244* | |
H4 | −0.2973 | −0.0681 | 0.1442 | 0.0242* | |
H5 | −0.0315 | −0.0638 | 0.2531 | 0.0203* | |
H6 | 0.2342 | −0.0384 | 0.5851 | 0.0222* | |
H7 | 0.3602 | −0.1101 | 0.1314 | 0.0209* | |
H8 | 0.4194 | −0.3092 | 0.0534 | 0.0251* | |
H9 | 0.4203 | −0.4472 | 0.1620 | 0.0277* | |
H10 | 0.3601 | −0.3847 | 0.3462 | 0.0266* | |
H11A | 0.9685 | 0.4372 | 0.1379 | 0.0257* | |
H12B | 0.9410 | 0.5304 | 0.2579 | 0.0257* | |
H13A | 0.7940 | 0.6446 | 0.1684 | 0.0336* | |
H14B | 0.8083 | 0.5484 | 0.0476 | 0.0336* | |
H15C | 0.9925 | 0.6435 | 0.1257 | 0.0336* | |
H16A | 0.2689 | 0.4041 | 0.6001 | 0.0280* | |
H17B | 0.0578 | 0.3469 | 0.5402 | 0.0280* | |
H18A | 0.1391 | 0.4052 | 0.3829 | 0.0279* | |
H19B | 0.3539 | 0.4514 | 0.4338 | 0.0279* | |
H20C | 0.2109 | 0.5301 | 0.4918 | 0.0279* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0248 (8) | 0.0220 (8) | 0.0254 (8) | 0.0006 (6) | −0.0014 (6) | 0.0159 (6) |
O2 | 0.0185 (7) | 0.0263 (8) | 0.0259 (8) | −0.0008 (6) | −0.0013 (6) | 0.0135 (7) |
O3 | 0.0173 (7) | 0.0230 (8) | 0.0266 (8) | −0.0041 (6) | 0.0017 (6) | 0.0151 (7) |
O4 | 0.0323 (9) | 0.0269 (8) | 0.0198 (8) | 0.0061 (7) | 0.0080 (7) | 0.0095 (7) |
O5 | 0.0333 (9) | 0.0193 (7) | 0.0195 (8) | 0.0094 (7) | 0.0091 (6) | 0.0088 (6) |
N1 | 0.0132 (8) | 0.0161 (8) | 0.0155 (8) | 0.0018 (6) | 0.0009 (6) | 0.0085 (7) |
N2 | 0.0180 (9) | 0.0231 (9) | 0.0247 (9) | 0.0027 (7) | 0.0017 (7) | 0.0151 (8) |
C1 | 0.0135 (9) | 0.0149 (9) | 0.0156 (9) | 0.0023 (7) | 0.0022 (7) | 0.0048 (8) |
C2 | 0.0142 (9) | 0.0157 (9) | 0.0143 (9) | 0.0024 (7) | 0.0019 (7) | 0.0049 (7) |
C3 | 0.0163 (9) | 0.0129 (9) | 0.0151 (9) | 0.0021 (7) | 0.0015 (7) | 0.0049 (7) |
C4 | 0.0200 (10) | 0.0177 (9) | 0.0171 (9) | 0.0064 (8) | 0.0029 (8) | 0.0070 (8) |
C5 | 0.0158 (9) | 0.0265 (11) | 0.0192 (10) | 0.0070 (8) | 0.0008 (8) | 0.0073 (9) |
C6 | 0.0147 (9) | 0.0241 (11) | 0.0209 (10) | 0.0020 (8) | 0.0029 (8) | 0.0079 (9) |
C7 | 0.0163 (9) | 0.0190 (10) | 0.0169 (9) | 0.0019 (8) | 0.0040 (7) | 0.0093 (8) |
C8 | 0.0153 (9) | 0.0146 (9) | 0.0134 (9) | 0.0038 (8) | 0.0024 (7) | 0.0042 (7) |
C9 | 0.0135 (9) | 0.0157 (9) | 0.0142 (9) | 0.0044 (7) | 0.0017 (7) | 0.0053 (8) |
C10 | 0.0168 (9) | 0.0139 (9) | 0.0158 (9) | 0.0007 (7) | 0.0037 (7) | 0.0051 (7) |
C11 | 0.0155 (10) | 0.0217 (10) | 0.0268 (11) | −0.0013 (8) | 0.0047 (8) | 0.0116 (9) |
C12 | 0.0221 (11) | 0.0270 (12) | 0.0379 (13) | 0.0001 (9) | 0.0045 (10) | 0.0189 (10) |
C13 | 0.0149 (9) | 0.0248 (10) | 0.0180 (9) | 0.0030 (8) | 0.0008 (8) | 0.0119 (8) |
C14 | 0.0123 (9) | 0.0199 (10) | 0.0179 (10) | 0.0004 (7) | −0.0002 (7) | 0.0100 (8) |
C15 | 0.0120 (9) | 0.0171 (9) | 0.0180 (9) | −0.0001 (7) | −0.0006 (7) | 0.0098 (8) |
C16 | 0.0130 (9) | 0.0194 (10) | 0.0206 (10) | 0.0006 (8) | 0.0019 (7) | 0.0102 (8) |
C17 | 0.0166 (10) | 0.0206 (10) | 0.0234 (10) | 0.0015 (8) | 0.0040 (8) | 0.0062 (8) |
C18 | 0.0182 (10) | 0.0176 (10) | 0.0332 (12) | 0.0040 (8) | 0.0026 (9) | 0.0083 (9) |
C19 | 0.0183 (10) | 0.0205 (10) | 0.0319 (12) | 0.0029 (8) | 0.0024 (9) | 0.0159 (9) |
C20 | 0.0109 (9) | 0.0165 (9) | 0.0199 (10) | 0.0001 (7) | −0.0005 (7) | 0.0083 (8) |
C21 | 0.0137 (9) | 0.0178 (10) | 0.0216 (10) | 0.0000 (8) | −0.0004 (8) | 0.0101 (8) |
C22 | 0.0131 (9) | 0.0220 (10) | 0.0167 (9) | 0.0001 (8) | −0.0003 (7) | 0.0092 (8) |
C23 | 0.0271 (11) | 0.0204 (10) | 0.0243 (11) | 0.0090 (9) | 0.0090 (9) | 0.0068 (9) |
C24 | 0.0229 (11) | 0.0223 (11) | 0.0252 (11) | 0.0062 (9) | 0.0014 (9) | 0.0085 (9) |
O1—C3 | 1.234 (3) | C16—C17 | 1.368 (3) |
O2—C10 | 1.210 (3) | C16—C20 | 1.419 (3) |
O3—C10 | 1.340 (3) | C17—C18 | 1.419 (4) |
O3—C11 | 1.462 (3) | C18—C19 | 1.365 (4) |
O4—C22 | 1.206 (3) | C19—C21 | 1.410 (3) |
O5—C22 | 1.332 (3) | C20—C21 | 1.422 (4) |
O5—C23 | 1.456 (3) | C23—C24 | 1.504 (4) |
N1—C1 | 1.353 (3) | C1—H1 | 0.950 |
N1—C9 | 1.402 (3) | C4—H2 | 0.950 |
N1—C15 | 1.445 (3) | C5—H3 | 0.950 |
N2—C13 | 1.312 (3) | C6—H4 | 0.950 |
N2—C21 | 1.377 (3) | C7—H5 | 0.950 |
C1—C2 | 1.372 (3) | C11—H11A | 0.990 |
C2—C3 | 1.457 (3) | C11—H12B | 0.990 |
C2—C10 | 1.490 (3) | C12—H13A | 0.980 |
C3—C8 | 1.484 (3) | C12—H14B | 0.980 |
C4—C5 | 1.374 (3) | C12—H15C | 0.980 |
C4—C8 | 1.405 (3) | C13—H6 | 0.950 |
C5—C6 | 1.400 (4) | C16—H7 | 0.950 |
C6—C7 | 1.379 (3) | C17—H8 | 0.950 |
C7—C9 | 1.401 (3) | C18—H9 | 0.950 |
C8—C9 | 1.399 (3) | C19—H10 | 0.950 |
C11—C12 | 1.506 (4) | C23—H16A | 0.990 |
C13—C14 | 1.429 (4) | C23—H17B | 0.990 |
C14—C15 | 1.377 (3) | C24—H18A | 0.980 |
C14—C22 | 1.493 (3) | C24—H19B | 0.980 |
C15—C20 | 1.418 (3) | C24—H20C | 0.980 |
O1···O3 | 2.721 (2) | C16···H3ix | 3.2503 |
O1···C4 | 2.797 (3) | C16···H4iv | 2.6347 |
O1···C10 | 3.054 (3) | C16···H15Cxii | 2.9958 |
O2···C1 | 2.728 (3) | C17···H4iv | 2.8881 |
O2···C11 | 2.668 (4) | C17···H13Ax | 3.3009 |
O3···C1 | 3.580 (3) | C17···H14Bii | 3.1314 |
O3···C3 | 2.872 (3) | C17···H15Cxii | 2.9258 |
O4···C13 | 2.788 (3) | C18···H11Axii | 3.3525 |
O4···C23 | 2.679 (4) | C18···H12Bxii | 3.5459 |
O5···N1 | 2.649 (3) | C18···H13Ax | 2.9809 |
O5···C1 | 3.000 (3) | C18···H14Bii | 3.1837 |
O5···C9 | 3.113 (3) | C18···H15Cxii | 3.1156 |
O5···C15 | 2.850 (3) | C19···H11Axii | 3.5303 |
N1···C3 | 2.862 (3) | C19···H12Bxii | 3.1146 |
N1···C16 | 2.862 (3) | C19···H15Cxii | 3.3449 |
N1···C22 | 3.053 (3) | C19···H16Avii | 3.3374 |
N2···C15 | 2.818 (4) | C19···H18Ax | 3.5463 |
C1···C8 | 2.765 (3) | C19···H19Bx | 3.3639 |
C1···C14 | 3.285 (4) | C19···H20Cx | 3.3479 |
C1···C16 | 3.485 (3) | C20···H4iv | 3.4608 |
C1···C20 | 3.269 (3) | C20···H6vii | 3.3943 |
C2···C9 | 2.834 (3) | C20···H15Cxii | 3.2647 |
C4···C7 | 2.791 (4) | C21···H12Bxii | 3.4887 |
C5···C9 | 2.773 (3) | C21···H15Cxii | 3.4265 |
C6···C8 | 2.794 (3) | C21···H17Bvi | 3.4823 |
C7···C14 | 3.482 (3) | C22···H5vi | 3.5442 |
C7···C15 | 2.828 (3) | C22···H6vi | 3.3471 |
C7···C20 | 3.422 (4) | C22···H10vii | 3.5672 |
C9···C14 | 3.346 (4) | C23···H10vii | 3.5622 |
C9···C16 | 3.450 (4) | C23···H12Bv | 2.9250 |
C9···C20 | 3.286 (4) | C23···H19Bv | 3.5003 |
C13···C19 | 3.581 (4) | C23···H20Cxiii | 3.4856 |
C13···C20 | 2.740 (3) | C24···H10iii | 2.7110 |
C14···C21 | 2.773 (3) | C24···H17Bxiii | 3.4851 |
C16···C19 | 2.792 (4) | C24···H19Bv | 3.1740 |
C17···C21 | 2.805 (3) | C24···H20Cxiii | 3.4241 |
C18···C20 | 2.805 (3) | H1···N2vii | 2.7418 |
O1···C12i | 3.487 (4) | H1···C6iv | 3.4832 |
O1···C17ii | 3.440 (3) | H1···C13vii | 3.0655 |
O1···C18iii | 3.285 (3) | H1···H4iv | 3.3676 |
O2···C4iv | 3.419 (3) | H1···H6vii | 2.7266 |
O2···C5iv | 3.400 (3) | H1···H20Cv | 3.4058 |
O2···C23v | 3.424 (3) | H2···O3viii | 3.5373 |
O2···C24iv | 3.366 (3) | H2···C6ix | 3.3689 |
O2···C24v | 3.378 (3) | H2···C7ix | 3.3674 |
O3···C17ii | 3.552 (3) | H2···C11viii | 3.3478 |
O4···N2vi | 3.526 (3) | H2···C12i | 3.5014 |
O4···C7vi | 3.363 (3) | H2···C16ix | 3.5155 |
O4···C13vi | 3.256 (3) | H2···H7ix | 3.0777 |
O4···C14vi | 3.366 (3) | H2···H11Aviii | 2.4907 |
O4···C19vii | 3.506 (3) | H2···H14Bi | 3.2824 |
N2···O4vi | 3.526 (3) | H2···H15Ci | 2.9882 |
N2···C1vii | 3.579 (3) | H3···C2viii | 3.3558 |
N2···C14vii | 3.324 (3) | H3···C8ix | 3.3698 |
N2···C15vii | 3.570 (3) | H3···C9ix | 3.4764 |
C1···N2vii | 3.579 (3) | H3···C10viii | 3.2903 |
C4···O2viii | 3.419 (3) | H3···C16ix | 3.2503 |
C4···C5ix | 3.444 (3) | H3···H3xiv | 3.2050 |
C4···C6ix | 3.445 (3) | H3···H7viii | 3.4521 |
C5···O2viii | 3.400 (3) | H3···H7ix | 2.3788 |
C5···C4ix | 3.444 (3) | H3···H8ix | 3.5271 |
C5···C8ix | 3.362 (3) | H4···O1ix | 3.3409 |
C5···C10viii | 3.414 (3) | H4···C1viii | 3.5997 |
C6···C4ix | 3.445 (3) | H4···C3ix | 3.5833 |
C6···C16viii | 3.550 (3) | H4···C16viii | 2.6347 |
C7···O4vi | 3.363 (3) | H4···C17viii | 2.8881 |
C8···C5ix | 3.362 (3) | H4···C20viii | 3.4608 |
C10···C5iv | 3.414 (3) | H4···H1viii | 3.3676 |
C12···O1i | 3.487 (4) | H4···H6vi | 3.2171 |
C13···O4vi | 3.256 (3) | H4···H7viii | 2.4759 |
C13···C13vii | 3.585 (3) | H4···H8viii | 2.9084 |
C13···C14vii | 3.524 (3) | H4···H13Axii | 3.5528 |
C13···C15vii | 3.527 (3) | H5···O4vi | 2.4848 |
C13···C22vi | 3.422 (3) | H5···C13vi | 3.5802 |
C14···O4vi | 3.366 (3) | H5···C22vi | 3.5442 |
C14···N2vii | 3.324 (3) | H5···H6vi | 2.7225 |
C14···C13vii | 3.524 (3) | H5···H13Axii | 3.0760 |
C14···C21vii | 3.591 (3) | H5···H15Cxii | 3.2508 |
C15···N2vii | 3.570 (3) | H6···O4vi | 3.5171 |
C15···C13vii | 3.527 (3) | H6···C1vii | 3.5653 |
C16···C6iv | 3.550 (3) | H6···C6vi | 3.3152 |
C17···O1ii | 3.440 (3) | H6···C7vi | 3.0373 |
C17···O3ii | 3.552 (3) | H6···C15vii | 3.4641 |
C18···O1x | 3.285 (3) | H6···C20vii | 3.3943 |
C19···O4vii | 3.506 (3) | H6···C22vi | 3.3471 |
C19···C22vii | 3.548 (3) | H6···H1vii | 2.7266 |
C21···C14vii | 3.591 (3) | H6···H4vi | 3.2171 |
C21···C22vii | 3.530 (3) | H6···H5vi | 2.7225 |
C22···C13vi | 3.422 (3) | H6···H17Bvi | 3.5016 |
C22···C19vii | 3.548 (3) | H7···C4ix | 3.4854 |
C22···C21vii | 3.530 (3) | H7···C5ix | 3.1398 |
C23···O2v | 3.424 (3) | H7···C6iv | 3.3133 |
C24···O2viii | 3.366 (3) | H7···H2ix | 3.0777 |
C24···O2v | 3.378 (3) | H7···H3iv | 3.4521 |
O1···H2 | 2.5024 | H7···H3ix | 2.3788 |
O2···H1 | 2.3541 | H7···H4iv | 2.4759 |
O2···H11A | 2.8600 | H7···H15Cxii | 3.4211 |
O2···H12B | 2.4509 | H8···O1ii | 2.6034 |
O3···H13A | 2.6002 | H8···O3ii | 2.6912 |
O3···H14B | 2.5486 | H8···C3ii | 3.3404 |
O3···H15C | 3.2399 | H8···C10ii | 3.5754 |
O4···H6 | 2.4392 | H8···C11ii | 3.3825 |
O4···H16A | 2.6354 | H8···C12ii | 3.4407 |
O4···H17B | 2.6916 | H8···H3ix | 3.5271 |
O5···H1 | 3.2272 | H8···H4iv | 2.9084 |
O5···H18A | 2.6002 | H8···H11Aii | 3.3950 |
O5···H19B | 2.5194 | H8···H13Ax | 3.2930 |
O5···H20C | 3.2261 | H8···H14Bii | 2.7242 |
N1···H5 | 2.6148 | H8···H15Cxii | 3.3256 |
N1···H7 | 2.5433 | H9···O1x | 2.4059 |
N2···H10 | 2.5667 | H9···O3x | 2.9268 |
C1···H7 | 3.0427 | H9···C3x | 3.2308 |
C1···H19B | 3.4704 | H9···C12x | 3.3470 |
C2···H19B | 3.2896 | H9···H11Axii | 3.2888 |
C3···H1 | 3.3018 | H9···H13Ax | 2.7331 |
C3···H2 | 2.6493 | H9···H14Bx | 3.2979 |
C3···H18A | 3.4876 | H9···H14Bii | 2.8269 |
C3···H19B | 3.5909 | H9···H16Avii | 3.5282 |
C4···H4 | 3.2566 | H10···O5vii | 3.4783 |
C5···H5 | 3.2740 | H10···C22vii | 3.5672 |
C6···H2 | 3.2599 | H10···C23vii | 3.5622 |
C7···H3 | 3.2681 | H10···C24x | 2.7110 |
C7···H7 | 3.4234 | H10···H11Axii | 3.5777 |
C8···H3 | 3.2732 | H10···H12Bxii | 3.0917 |
C8···H5 | 3.2941 | H10···H16Avii | 2.8818 |
C8···H18A | 3.3630 | H10···H17Bvi | 3.5483 |
C9···H1 | 3.2388 | H10···H18Ax | 2.7485 |
C9···H2 | 3.2679 | H10···H19Bx | 2.4185 |
C9···H4 | 3.2564 | H10···H20Cx | 2.5150 |
C9···H7 | 2.9583 | H11A···O1iv | 3.2773 |
C10···H1 | 2.4837 | H11A···C4iv | 3.0440 |
C10···H11A | 2.7433 | H11A···C12xi | 3.5332 |
C10···H12B | 2.5328 | H11A···C18xv | 3.3525 |
C14···H1 | 3.2488 | H11A···C19xv | 3.5303 |
C14···H5 | 2.9872 | H11A···H2iv | 2.4907 |
C15···H1 | 2.5425 | H11A···H8ii | 3.3950 |
C15···H5 | 2.4890 | H11A···H9xv | 3.2888 |
C15···H6 | 3.2376 | H11A···H10xv | 3.5777 |
C15···H7 | 2.6946 | H11A···H14Bxi | 2.9576 |
C16···H5 | 3.4501 | H11A···H15Cxi | 3.2071 |
C16···H9 | 3.2684 | H11A···H18Aiv | 3.4247 |
C17···H10 | 3.2702 | H12B···O4v | 3.5621 |
C18···H7 | 3.2742 | H12B···C18xv | 3.5459 |
C19···H8 | 3.2649 | H12B···C19xv | 3.1146 |
C20···H1 | 3.2870 | H12B···C21xv | 3.4887 |
C20···H5 | 2.9435 | H12B···C23v | 2.9250 |
C20···H8 | 3.2797 | H12B···H10xv | 3.0917 |
C20···H10 | 3.2989 | H12B···H16Av | 2.4860 |
C21···H6 | 3.1519 | H12B···H17Bv | 2.4932 |
C21···H7 | 3.3053 | H12B···H18Aiv | 2.9489 |
C21···H9 | 3.2729 | H12B···H20Civ | 3.4795 |
C22···H6 | 2.5672 | H13A···O1i | 3.4433 |
C22···H16A | 2.6191 | H13A···O4v | 2.8541 |
C22···H17B | 2.6478 | H13A···C17iii | 3.3009 |
H1···H7 | 3.3618 | H13A···C18iii | 2.9809 |
H2···H3 | 2.3180 | H13A···H4xv | 3.5528 |
H3···H4 | 2.3455 | H13A···H5xv | 3.0760 |
H4···H5 | 2.3310 | H13A···H8iii | 3.2930 |
H5···H7 | 3.4322 | H13A···H9iii | 2.7331 |
H7···H8 | 2.3115 | H13A···H16Av | 3.1643 |
H8···H9 | 2.3664 | H14B···O1i | 2.8415 |
H9···H10 | 2.3060 | H14B···C17ii | 3.1314 |
H11A···H13A | 2.8577 | H14B···C18ii | 3.1837 |
H11A···H14B | 2.3845 | H14B···H2i | 3.2824 |
H11A···H15C | 2.3470 | H14B···H8ii | 2.7242 |
H12B···H13A | 2.3474 | H14B···H9iii | 3.2979 |
H12B···H14B | 2.8576 | H14B···H9ii | 2.8269 |
H12B···H15C | 2.3843 | H14B···H11Axi | 2.9576 |
H16A···H18A | 2.8558 | H14B···H14Bxi | 3.4237 |
H16A···H19B | 2.3937 | H14B···H15Cxi | 3.2436 |
H16A···H20C | 2.3365 | H15C···C16xv | 2.9958 |
H17B···H18A | 2.3357 | H15C···C17xv | 2.9258 |
H17B···H19B | 2.8557 | H15C···C18xv | 3.1156 |
H17B···H20C | 2.3946 | H15C···C19xv | 3.3449 |
O1···H4ix | 3.3409 | H15C···C20xv | 3.2647 |
O1···H8ii | 2.6034 | H15C···C21xv | 3.4265 |
O1···H9iii | 2.4059 | H15C···H2i | 2.9882 |
O1···H11Aviii | 3.2773 | H15C···H5xv | 3.2508 |
O1···H13Ai | 3.4433 | H15C···H7xv | 3.4211 |
O1···H14Bi | 2.8415 | H15C···H8xv | 3.3256 |
O2···H16Av | 2.9985 | H15C···H11Axi | 3.2071 |
O2···H17Biv | 3.4220 | H15C···H14Bxi | 3.2436 |
O2···H17Bv | 3.4154 | H16A···O2v | 2.9985 |
O2···H18Aiv | 2.5154 | H16A···O3v | 2.9902 |
O2···H20Civ | 3.5896 | H16A···C10v | 2.9668 |
O2···H20Cv | 2.5977 | H16A···C11v | 3.0820 |
O3···H2iv | 3.5373 | H16A···C19vii | 3.3374 |
O3···H8ii | 2.6912 | H16A···H9vii | 3.5282 |
O3···H9iii | 2.9268 | H16A···H10vii | 2.8818 |
O3···H16Av | 2.9902 | H16A···H12Bv | 2.4860 |
O4···H5vi | 2.4848 | H16A···H13Av | 3.1643 |
O4···H6vi | 3.5171 | H16A···H19Bv | 3.0400 |
O4···H12Bv | 3.5621 | H17B···O2viii | 3.4220 |
O4···H13Av | 2.8541 | H17B···O2v | 3.4154 |
O5···H10vii | 3.4783 | H17B···N2vi | 2.8767 |
N2···H1vii | 2.7418 | H17B···C11v | 3.4166 |
N2···H17Bvi | 2.8767 | H17B···C13vi | 3.4118 |
N2···H20Cx | 3.3870 | H17B···C21vi | 3.4823 |
C1···H4iv | 3.5997 | H17B···C24xiii | 3.4851 |
C1···H6vii | 3.5653 | H17B···H6vi | 3.5016 |
C2···H3iv | 3.3558 | H17B···H10vi | 3.5483 |
C3···H4ix | 3.5833 | H17B···H12Bv | 2.4932 |
C3···H8ii | 3.3404 | H17B···H18Axiii | 3.3506 |
C3···H9iii | 3.2308 | H17B···H20Cxiii | 2.7540 |
C4···H7ix | 3.4854 | H18A···O2viii | 2.5154 |
C4···H11Aviii | 3.0440 | H18A···C11viii | 3.5891 |
C5···H7ix | 3.1398 | H18A···C19iii | 3.5463 |
C6···H1viii | 3.4832 | H18A···H10iii | 2.7485 |
C6···H2ix | 3.3689 | H18A···H11Aviii | 3.4247 |
C6···H6vi | 3.3152 | H18A···H12Bviii | 2.9489 |
C6···H7viii | 3.3133 | H18A···H17Bxiii | 3.3506 |
C7···H2ix | 3.3674 | H18A···H20Cxiii | 3.2218 |
C7···H6vi | 3.0373 | H19B···C19iii | 3.3639 |
C8···H3ix | 3.3698 | H19B···C23v | 3.5003 |
C9···H3ix | 3.4764 | H19B···C24v | 3.1740 |
C10···H3iv | 3.2903 | H19B···H10iii | 2.4185 |
C10···H8ii | 3.5754 | H19B···H16Av | 3.0400 |
C10···H16Av | 2.9668 | H19B···H19Bv | 2.4826 |
C10···H20Cv | 3.2797 | H19B···H20Cv | 3.2698 |
C11···H2iv | 3.3478 | H20C···O2viii | 3.5896 |
C11···H8ii | 3.3825 | H20C···O2v | 2.5977 |
C11···H16Av | 3.0820 | H20C···N2iii | 3.3870 |
C11···H17Bv | 3.4166 | H20C···C10v | 3.2797 |
C11···H18Aiv | 3.5891 | H20C···C19iii | 3.3479 |
C12···H2i | 3.5014 | H20C···C23xiii | 3.4856 |
C12···H8ii | 3.4407 | H20C···C24xiii | 3.4241 |
C12···H9iii | 3.3470 | H20C···H1v | 3.4058 |
C12···H11Axi | 3.5332 | H20C···H10iii | 2.5150 |
C13···H1vii | 3.0655 | H20C···H12Bviii | 3.4795 |
C13···H5vi | 3.5802 | H20C···H17Bxiii | 2.7540 |
C13···H17Bvi | 3.4118 | H20C···H18Axiii | 3.2218 |
C15···H6vii | 3.4641 | H20C···H19Bv | 3.2698 |
C16···H2ix | 3.5155 | H20C···H20Cxiii | 3.0947 |
C10—O3—C11 | 116.03 (17) | O4—C22—C14 | 122.8 (2) |
C22—O5—C23 | 116.67 (17) | O5—C22—C14 | 113.12 (18) |
C1—N1—C9 | 120.57 (19) | O5—C23—C24 | 106.50 (18) |
C1—N1—C15 | 119.36 (17) | N1—C1—H1 | 118.012 |
C9—N1—C15 | 120.07 (15) | C2—C1—H1 | 118.004 |
C13—N2—C21 | 117.3 (2) | C5—C4—H2 | 119.617 |
N1—C1—C2 | 123.98 (18) | C8—C4—H2 | 119.625 |
C1—C2—C3 | 120.06 (16) | C4—C5—H3 | 119.978 |
C1—C2—C10 | 114.17 (18) | C6—C5—H3 | 119.971 |
C3—C2—C10 | 125.77 (19) | C5—C6—H4 | 119.697 |
O1—C3—C2 | 125.66 (17) | C7—C6—H4 | 119.692 |
O1—C3—C8 | 119.87 (18) | C6—C7—H5 | 120.452 |
C2—C3—C8 | 114.47 (19) | C9—C7—H5 | 120.455 |
C5—C4—C8 | 120.8 (2) | O3—C11—H11A | 110.326 |
C4—C5—C6 | 120.1 (2) | O3—C11—H12B | 110.317 |
C5—C6—C7 | 120.61 (18) | C12—C11—H11A | 110.316 |
C6—C7—C9 | 119.1 (2) | C12—C11—H12B | 110.320 |
C3—C8—C4 | 119.6 (2) | H11A—C11—H12B | 108.569 |
C3—C8—C9 | 122.01 (18) | C11—C12—H13A | 109.471 |
C4—C8—C9 | 118.38 (17) | C11—C12—H14B | 109.471 |
N1—C9—C7 | 120.1 (2) | C11—C12—H15C | 109.470 |
N1—C9—C8 | 118.82 (16) | H13A—C12—H14B | 109.471 |
C7—C9—C8 | 121.09 (19) | H13A—C12—H15C | 109.466 |
O2—C10—O3 | 123.53 (17) | H14B—C12—H15C | 109.479 |
O2—C10—C2 | 123.3 (2) | N2—C13—H6 | 117.274 |
O3—C10—C2 | 113.22 (18) | C14—C13—H6 | 117.275 |
O3—C11—C12 | 106.99 (18) | C17—C16—H7 | 119.663 |
N2—C13—C14 | 125.5 (2) | C20—C16—H7 | 119.668 |
C13—C14—C15 | 116.96 (19) | C16—C17—H8 | 119.901 |
C13—C14—C22 | 116.01 (18) | C18—C17—H8 | 119.897 |
C15—C14—C22 | 127.0 (2) | C17—C18—H9 | 119.931 |
N1—C15—C14 | 122.56 (18) | C19—C18—H9 | 119.919 |
N1—C15—C20 | 117.19 (18) | C18—C19—H10 | 119.481 |
C14—C15—C20 | 120.3 (2) | C21—C19—H10 | 119.469 |
C17—C16—C20 | 120.7 (3) | O5—C23—H16A | 110.426 |
C16—C17—C18 | 120.2 (2) | O5—C23—H17B | 110.425 |
C17—C18—C19 | 120.1 (2) | C24—C23—H16A | 110.425 |
C18—C19—C21 | 121.1 (3) | C24—C23—H17B | 110.428 |
C15—C20—C16 | 123.4 (2) | H16A—C23—H17B | 108.636 |
C15—C20—C21 | 117.64 (18) | C23—C24—H18A | 109.469 |
C16—C20—C21 | 118.91 (18) | C23—C24—H19B | 109.467 |
N2—C21—C19 | 118.7 (2) | C23—C24—H20C | 109.462 |
N2—C21—C20 | 122.31 (18) | H18A—C24—H19B | 109.476 |
C19—C21—C20 | 119.01 (19) | H18A—C24—H20C | 109.473 |
O4—C22—O5 | 124.09 (19) | H19B—C24—H20C | 109.480 |
C10—O3—C11—C12 | −163.33 (14) | C3—C8—C9—N1 | 1.7 (3) |
C10—O3—C11—H11A | 76.6 | C3—C8—C9—C7 | −177.41 (14) |
C10—O3—C11—H12B | −43.3 | C4—C8—C9—N1 | −179.99 (15) |
C11—O3—C10—O2 | 1.9 (3) | C4—C8—C9—C7 | 0.9 (3) |
C11—O3—C10—C2 | −178.65 (13) | O3—C11—C12—H13A | 63.4 |
C22—O5—C23—C24 | 177.74 (14) | O3—C11—C12—H14B | −56.6 |
C22—O5—C23—H16A | 57.8 | O3—C11—C12—H15C | −176.6 |
C22—O5—C23—H17B | −62.3 | H11A—C11—C12—H13A | −176.6 |
C23—O5—C22—O4 | −0.3 (3) | H11A—C11—C12—H14B | 63.4 |
C23—O5—C22—C14 | 179.11 (13) | H11A—C11—C12—H15C | −56.6 |
C1—N1—C9—C7 | −179.62 (14) | H12B—C11—C12—H13A | −56.6 |
C1—N1—C9—C8 | 1.3 (3) | H12B—C11—C12—H14B | −176.6 |
C9—N1—C1—C2 | −2.6 (3) | H12B—C11—C12—H15C | 63.4 |
C9—N1—C1—H1 | 177.4 | N2—C13—C14—C15 | −0.1 (3) |
C1—N1—C15—C14 | 88.7 (2) | N2—C13—C14—C22 | 179.21 (15) |
C1—N1—C15—C20 | −92.14 (18) | H6—C13—C14—C15 | 179.9 |
C15—N1—C1—C2 | 178.02 (14) | H6—C13—C14—C22 | −0.8 |
C15—N1—C1—H1 | −2.0 | C13—C14—C15—N1 | −179.07 (14) |
C9—N1—C15—C14 | −90.68 (19) | C13—C14—C15—C20 | 1.8 (3) |
C9—N1—C15—C20 | 88.5 (2) | C13—C14—C22—O4 | −6.1 (3) |
C15—N1—C9—C7 | −0.2 (3) | C13—C14—C22—O5 | 174.47 (14) |
C15—N1—C9—C8 | −179.35 (14) | C15—C14—C22—O4 | 173.10 (16) |
C13—N2—C21—C19 | −179.53 (15) | C15—C14—C22—O5 | −6.3 (3) |
C13—N2—C21—C20 | 0.3 (3) | C22—C14—C15—N1 | 1.7 (3) |
C21—N2—C13—C14 | −0.9 (3) | C22—C14—C15—C20 | −177.43 (15) |
C21—N2—C13—H6 | 179.0 | N1—C15—C20—C16 | −1.1 (3) |
N1—C1—C2—C3 | 0.8 (3) | N1—C15—C20—C21 | 178.46 (13) |
N1—C1—C2—C10 | −178.65 (15) | C14—C15—C20—C16 | 178.09 (15) |
H1—C1—C2—C3 | −179.2 | C14—C15—C20—C21 | −2.4 (3) |
H1—C1—C2—C10 | 1.3 | C17—C16—C20—C15 | 178.37 (15) |
C1—C2—C3—O1 | −178.32 (16) | C17—C16—C20—C21 | −1.2 (3) |
C1—C2—C3—C8 | 2.0 (3) | C20—C16—C17—C18 | 0.7 (3) |
C1—C2—C10—O2 | −4.8 (3) | C20—C16—C17—H8 | −179.3 |
C1—C2—C10—O3 | 175.71 (15) | H7—C16—C17—C18 | −179.3 |
C3—C2—C10—O2 | 175.77 (16) | H7—C16—C17—H8 | 0.7 |
C3—C2—C10—O3 | −3.7 (3) | H7—C16—C20—C15 | −1.6 |
C10—C2—C3—O1 | 1.1 (3) | H7—C16—C20—C21 | 178.8 |
C10—C2—C3—C8 | −178.61 (15) | C16—C17—C18—C19 | 0.3 (3) |
O1—C3—C8—C4 | −1.2 (3) | C16—C17—C18—H9 | −179.7 |
O1—C3—C8—C9 | 177.06 (15) | H8—C17—C18—C19 | −179.7 |
C2—C3—C8—C4 | 178.49 (14) | H8—C17—C18—H9 | 0.3 |
C2—C3—C8—C9 | −3.2 (3) | C17—C18—C19—C21 | −0.7 (3) |
C5—C4—C8—C3 | 178.51 (15) | C17—C18—C19—H10 | 179.3 |
C5—C4—C8—C9 | 0.2 (3) | H9—C18—C19—C21 | 179.2 |
C8—C4—C5—C6 | −1.0 (3) | H9—C18—C19—H10 | −0.8 |
C8—C4—C5—H3 | 178.9 | C18—C19—C21—N2 | −179.92 (16) |
H2—C4—C5—C6 | 179.0 | C18—C19—C21—C20 | 0.2 (3) |
H2—C4—C5—H3 | −1.0 | H10—C19—C21—N2 | 0.1 |
H2—C4—C8—C3 | −1.5 | H10—C19—C21—C20 | −179.8 |
H2—C4—C8—C9 | −179.8 | C15—C20—C21—N2 | 1.3 (3) |
C4—C5—C6—C7 | 0.9 (3) | C15—C20—C21—C19 | −178.85 (14) |
C4—C5—C6—H4 | −179.1 | C16—C20—C21—N2 | −179.13 (14) |
H3—C5—C6—C7 | −179.1 | C16—C20—C21—C19 | 0.7 (3) |
H3—C5—C6—H4 | 0.9 | O5—C23—C24—H18A | 65.3 |
C5—C6—C7—C9 | 0.1 (3) | O5—C23—C24—H19B | −54.7 |
C5—C6—C7—H5 | −179.9 | O5—C23—C24—H20C | −174.7 |
H4—C6—C7—C9 | −179.9 | H16A—C23—C24—H18A | −174.8 |
H4—C6—C7—H5 | 0.1 | H16A—C23—C24—H19B | 65.2 |
C6—C7—C9—N1 | 179.86 (15) | H16A—C23—C24—H20C | −54.8 |
C6—C7—C9—C8 | −1.0 (3) | H17B—C23—C24—H18A | −54.6 |
H5—C7—C9—N1 | −0.1 | H17B—C23—C24—H19B | −174.6 |
H5—C7—C9—C8 | 179.0 | H17B—C23—C24—H20C | 65.4 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, −y, −z; (iii) x, y+1, z; (iv) x+1, y, z; (v) −x+1, −y+1, −z+1; (vi) −x, −y, −z+1; (vii) −x+1, −y, −z+1; (viii) x−1, y, z; (ix) −x, −y, −z; (x) x, y−1, z; (xi) −x+2, −y+1, −z; (xii) x−1, y−1, z; (xiii) −x, −y+1, −z+1; (xiv) −x−1, −y, −z; (xv) x+1, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C24H20N2O5 |
Mr | 416.43 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 100 |
a, b, c (Å) | 7.4478 (16), 11.284 (5), 12.583 (5) |
α, β, γ (°) | 107.78 (3), 92.96 (3), 102.85 (3) |
V (Å3) | 973.5 (6) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.25 × 0.20 × 0.15 |
Data collection | |
Diffractometer | Rigaku AFC-7R diffractometer |
Absorption correction | – |
No. of measured, independent and observed [F2 > 2σ(F2)] reflections | 5486, 4479, 3077 |
Rint | 0.034 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.052, 0.159, 1.02 |
No. of reflections | 4479 |
No. of parameters | 282 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.26, −0.31 |
Computer programs: WinAFC Diffractometer Control Software (Rigaku, 1999), SIR2008 (Burla et al., 2007), SHELXL97 (Sheldrick, 2008), CrystalStructure (Rigaku, 2010).
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, and thank Professor Kei Manabe (University of Shizuoka, Japan) for helpful discussions.
References
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G., Siliqi, D. & Spagna, R. (2007). J. Appl. Cryst. 40, 609–613. Web of Science CrossRef CAS IUCr Journals Google Scholar
Ishikawa, Y. & Fujii, S. (2011). Bioinformation, 6, 221–225. CrossRef PubMed Google Scholar
Kajihara, S. (1965). Nippon Kagaku Zasshi, 86, 933–941. CrossRef CAS Google Scholar
Rigaku (1999). WinAFC Diffractometer Control Software. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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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 the metalloenzyme HIV integrase. According to our inhibitor design targeting the metalloenzyme influenza virus RNA polymerase (Ishikawa & Fujii, 2011), we tried to synthesize a 4-quinolone derivative bearing a benzensulfonyl group. 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 gave the white solid after purification by silica gel chromatography (Fig.1).
The crystallographic analysis revealed that it is a self-condensation product of ethyl 4-oxo-1,4-dihydroquinoline-3-carboxylate with a loss of one water molecule, as shown in Fig.2. This structure well accounts for the 1H NMR and MS spectra. The C–N bond formation should occur via the formation of a benzenesulfonate intermediate. The quinoline rings are approximately perpendicular to each other [dihedral angle = 90.94 (3)°]. In the crystal, the molecule is assembled via stacking interaction with its inversion equivalentsi,ii [centroid-centroid distances between the benzene rings of the upper quinoline units = 3.641 (2) Å (i: -x, -y, -z) and between the pyridine rings of the lower quinoline units = 3.592 (2) Å (ii: -x + 1, -y, -z + 1)]. As a result, the molecules form chains along [101] direction, as shown in Fig.3. Report on the synthesis of 1,4'-quinolines is scarce (Kajihara, 1965).