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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

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

(Received 25 March 2014; accepted 1 April 2014; online 5 April 2014)

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].

Related literature

For the background to this study, see: Ishikawa & Fujii (2011[Ishikawa, Y. & Fujii, S. (2011). Bioinformation, 6, 221-225.]). For a related compound, see: Kajihara (1965[Kajihara, S. (1965). Nippon Kagaku Zasshi, 86, 933-941.]).

[Scheme 1]

Experimental

Crystal data
  • C24H20N2O5

  • Mr = 416.43

  • Triclinic, [P \overline 1]

  • a = 7.4478 (16) Å

  • b = 11.284 (5) Å

  • c = 12.583 (5) Å

  • α = 107.78 (3)°

  • β = 92.96 (3)°

  • γ = 102.85 (3)°

  • V = 973.5 (6) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 100 K

  • 0.25 × 0.20 × 0.15 mm

Data collection
  • Rigaku AFC-7R diffractometer

  • 5486 measured reflections

  • 4479 independent reflections

  • 3077 reflections with F2 > 2σ(F2)

  • Rint = 0.034

  • 3 standard reflections every 150 reflections intensity decay: −0.2%

Refinement
  • R[F2 > 2σ(F2)] = 0.052

  • wR(F2) = 0.159

  • S = 1.02

  • 4479 reflections

  • 282 parameters

  • H-atom parameters constrained

  • Δρmax = 0.26 e Å−3

  • Δρmin = −0.31 e Å−3

Data collection: WinAFC Diffractometer Control Software (Rigaku, 1999[Rigaku (1999). WinAFC Diffractometer Control Software. Rigaku Corporation, Tokyo, Japan.]); cell refinement: WinAFC Diffractometer Control Software; data reduction: WinAFC Diffractometer Control Software; program(s) used to solve structure: SIR2008 (Burla et al., 2007[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.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: CrystalStructure (Rigaku, 2010[Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.]); software used to prepare material for publication: CrystalStructure.

Supporting information


Comment top

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).

Related literature top

For the background to this study, see: Ishikawa & Fujii (2011). For a related compound, see: Kajihara (1965).

Experimental top

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 column chromatography on silica gel (ethyl acetate: ethanol = 180: 5, yield: 33%). 1H NMR (400 MHz, DMSO-d6): 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.

Refinement top

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)].

Computing details top

Data collection: WinAFC Diffractometer Control Software (Rigaku, 1999); cell refinement: 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).

Figures top
[Figure 1] Fig. 1. Reaction scheme for the title compound.
[Figure 2] Fig. 2. The molecular structure of the title compound, with displacement ellipsoids drawn at the 50% probability level. Hydrogen atoms are shown as small spheres of arbitrary radius.
[Figure 3] Fig. 3. A crystal packing view of the title compound.
Diethyl 4-oxo-4H-[1,4'-biquinoline]-3,3'-dicarboxylate top
Crystal data top
C24H20N2O5Z = 2
Mr = 416.43F(000) = 436.00
Triclinic, P1Dx = 1.421 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71069 Å
a = 7.4478 (16) ÅCell parameters from 25 reflections
b = 11.284 (5) Åθ = 15.3–17.3°
c = 12.583 (5) ŵ = 0.10 mm1
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
Data collection top
Rigaku AFC-7R
diffractometer
θmax = 27.5°
ω–2θ scansh = 95
5486 measured reflectionsk = 1414
4479 independent reflectionsl = 1616
3077 reflections with F2 > 2σ(F2)3 standard reflections every 150 reflections
Rint = 0.034 intensity decay: 0.2%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159H-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 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.31 e Å3
Primary atom site location: structure-invariant direct methods
Crystal data top
C24H20N2O5γ = 102.85 (3)°
Mr = 416.43V = 973.5 (6) Å3
Triclinic, P1Z = 2
a = 7.4478 (16) ÅMo Kα radiation
b = 11.284 (5) ŵ = 0.10 mm1
c = 12.583 (5) ÅT = 100 K
α = 107.78 (3)°0.25 × 0.20 × 0.15 mm
β = 92.96 (3)°
Data collection top
Rigaku AFC-7R
diffractometer
Rint = 0.034
5486 measured reflections3 standard reflections every 150 reflections
4479 independent reflections intensity decay: 0.2%
3077 reflections with F2 > 2σ(F2)
Refinement top
R[F2 > 2σ(F2)] = 0.0520 restraints
wR(F2) = 0.159H-atom parameters constrained
S = 1.02Δρmax = 0.26 e Å3
4479 reflectionsΔρmin = 0.31 e Å3
282 parameters
Special details top

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).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.3332 (2)0.32182 (13)0.08577 (12)0.0232 (4)
O20.80212 (19)0.33534 (14)0.30167 (12)0.0236 (4)
O30.69998 (19)0.40856 (13)0.16873 (12)0.0222 (4)
O40.1676 (2)0.17036 (14)0.61313 (12)0.0259 (4)
O50.2323 (2)0.24073 (13)0.46750 (12)0.0228 (4)
N10.3020 (2)0.08516 (14)0.27797 (13)0.0145 (4)
N20.2925 (3)0.17369 (16)0.46462 (14)0.0206 (4)
C10.4640 (3)0.16992 (17)0.28111 (15)0.0149 (4)
C20.4860 (3)0.25268 (17)0.21964 (15)0.0149 (4)
C30.3287 (3)0.25386 (17)0.14649 (15)0.0150 (4)
C40.0110 (3)0.15898 (18)0.08414 (16)0.0177 (4)
C50.1760 (3)0.07462 (19)0.08318 (16)0.0203 (4)
C60.1832 (3)0.00914 (19)0.14607 (16)0.0202 (5)
C70.0263 (3)0.00679 (18)0.21064 (16)0.0170 (4)
C80.1514 (3)0.16402 (17)0.14924 (15)0.0145 (4)
C90.1409 (3)0.08087 (17)0.21275 (15)0.0142 (4)
C100.6784 (3)0.33482 (17)0.23514 (16)0.0159 (4)
C110.8869 (3)0.48947 (19)0.17788 (18)0.0214 (5)
C120.8689 (3)0.5903 (2)0.1253 (2)0.0280 (5)
C130.2596 (3)0.06055 (19)0.50924 (17)0.0185 (4)
C140.2587 (3)0.03214 (18)0.45333 (16)0.0165 (4)
C150.2959 (3)0.00050 (17)0.34353 (16)0.0155 (4)
C160.3614 (3)0.16464 (18)0.17583 (16)0.0174 (4)
C170.3957 (3)0.28265 (19)0.12941 (17)0.0209 (5)
C180.3959 (3)0.36552 (19)0.19449 (18)0.0231 (5)
C190.3611 (3)0.32810 (19)0.30362 (18)0.0222 (5)
C200.3277 (3)0.12283 (17)0.28961 (16)0.0159 (4)
C210.3266 (3)0.20668 (18)0.35423 (16)0.0176 (4)
C220.2150 (3)0.15395 (18)0.52060 (16)0.0174 (4)
C230.1895 (3)0.36186 (19)0.52667 (18)0.0233 (5)
C240.2266 (3)0.44432 (19)0.45232 (18)0.0233 (5)
H10.56880.17230.32880.0179*
H20.00660.21450.04030.0212*
H30.28520.07310.03980.0244*
H40.29730.06810.14420.0242*
H50.03150.06380.25310.0203*
H60.23420.03840.58510.0222*
H70.36020.11010.13140.0209*
H80.41940.30920.05340.0251*
H90.42030.44720.16200.0277*
H100.36010.38470.34620.0266*
H11A0.96850.43720.13790.0257*
H12B0.94100.53040.25790.0257*
H13A0.79400.64460.16840.0336*
H14B0.80830.54840.04760.0336*
H15C0.99250.64350.12570.0336*
H16A0.26890.40410.60010.0280*
H17B0.05780.34690.54020.0280*
H18A0.13910.40520.38290.0279*
H19B0.35390.45140.43380.0279*
H20C0.21090.53010.49180.0279*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0248 (8)0.0220 (8)0.0254 (8)0.0006 (6)0.0014 (6)0.0159 (6)
O20.0185 (7)0.0263 (8)0.0259 (8)0.0008 (6)0.0013 (6)0.0135 (7)
O30.0173 (7)0.0230 (8)0.0266 (8)0.0041 (6)0.0017 (6)0.0151 (7)
O40.0323 (9)0.0269 (8)0.0198 (8)0.0061 (7)0.0080 (7)0.0095 (7)
O50.0333 (9)0.0193 (7)0.0195 (8)0.0094 (7)0.0091 (6)0.0088 (6)
N10.0132 (8)0.0161 (8)0.0155 (8)0.0018 (6)0.0009 (6)0.0085 (7)
N20.0180 (9)0.0231 (9)0.0247 (9)0.0027 (7)0.0017 (7)0.0151 (8)
C10.0135 (9)0.0149 (9)0.0156 (9)0.0023 (7)0.0022 (7)0.0048 (8)
C20.0142 (9)0.0157 (9)0.0143 (9)0.0024 (7)0.0019 (7)0.0049 (7)
C30.0163 (9)0.0129 (9)0.0151 (9)0.0021 (7)0.0015 (7)0.0049 (7)
C40.0200 (10)0.0177 (9)0.0171 (9)0.0064 (8)0.0029 (8)0.0070 (8)
C50.0158 (9)0.0265 (11)0.0192 (10)0.0070 (8)0.0008 (8)0.0073 (9)
C60.0147 (9)0.0241 (11)0.0209 (10)0.0020 (8)0.0029 (8)0.0079 (9)
C70.0163 (9)0.0190 (10)0.0169 (9)0.0019 (8)0.0040 (7)0.0093 (8)
C80.0153 (9)0.0146 (9)0.0134 (9)0.0038 (8)0.0024 (7)0.0042 (7)
C90.0135 (9)0.0157 (9)0.0142 (9)0.0044 (7)0.0017 (7)0.0053 (8)
C100.0168 (9)0.0139 (9)0.0158 (9)0.0007 (7)0.0037 (7)0.0051 (7)
C110.0155 (10)0.0217 (10)0.0268 (11)0.0013 (8)0.0047 (8)0.0116 (9)
C120.0221 (11)0.0270 (12)0.0379 (13)0.0001 (9)0.0045 (10)0.0189 (10)
C130.0149 (9)0.0248 (10)0.0180 (9)0.0030 (8)0.0008 (8)0.0119 (8)
C140.0123 (9)0.0199 (10)0.0179 (10)0.0004 (7)0.0002 (7)0.0100 (8)
C150.0120 (9)0.0171 (9)0.0180 (9)0.0001 (7)0.0006 (7)0.0098 (8)
C160.0130 (9)0.0194 (10)0.0206 (10)0.0006 (8)0.0019 (7)0.0102 (8)
C170.0166 (10)0.0206 (10)0.0234 (10)0.0015 (8)0.0040 (8)0.0062 (8)
C180.0182 (10)0.0176 (10)0.0332 (12)0.0040 (8)0.0026 (9)0.0083 (9)
C190.0183 (10)0.0205 (10)0.0319 (12)0.0029 (8)0.0024 (9)0.0159 (9)
C200.0109 (9)0.0165 (9)0.0199 (10)0.0001 (7)0.0005 (7)0.0083 (8)
C210.0137 (9)0.0178 (10)0.0216 (10)0.0000 (8)0.0004 (8)0.0101 (8)
C220.0131 (9)0.0220 (10)0.0167 (9)0.0001 (8)0.0003 (7)0.0092 (8)
C230.0271 (11)0.0204 (10)0.0243 (11)0.0090 (9)0.0090 (9)0.0068 (9)
C240.0229 (11)0.0223 (11)0.0252 (11)0.0062 (9)0.0014 (9)0.0085 (9)
Geometric parameters (Å, º) top
O1—C31.234 (3)C16—C171.368 (3)
O2—C101.210 (3)C16—C201.419 (3)
O3—C101.340 (3)C17—C181.419 (4)
O3—C111.462 (3)C18—C191.365 (4)
O4—C221.206 (3)C19—C211.410 (3)
O5—C221.332 (3)C20—C211.422 (4)
O5—C231.456 (3)C23—C241.504 (4)
N1—C11.353 (3)C1—H10.950
N1—C91.402 (3)C4—H20.950
N1—C151.445 (3)C5—H30.950
N2—C131.312 (3)C6—H40.950
N2—C211.377 (3)C7—H50.950
C1—C21.372 (3)C11—H11A0.990
C2—C31.457 (3)C11—H12B0.990
C2—C101.490 (3)C12—H13A0.980
C3—C81.484 (3)C12—H14B0.980
C4—C51.374 (3)C12—H15C0.980
C4—C81.405 (3)C13—H60.950
C5—C61.400 (4)C16—H70.950
C6—C71.379 (3)C17—H80.950
C7—C91.401 (3)C18—H90.950
C8—C91.399 (3)C19—H100.950
C11—C121.506 (4)C23—H16A0.990
C13—C141.429 (4)C23—H17B0.990
C14—C151.377 (3)C24—H18A0.980
C14—C221.493 (3)C24—H19B0.980
C15—C201.418 (3)C24—H20C0.980
O1···O32.721 (2)C16···H3ix3.2503
O1···C42.797 (3)C16···H4iv2.6347
O1···C103.054 (3)C16···H15Cxii2.9958
O2···C12.728 (3)C17···H4iv2.8881
O2···C112.668 (4)C17···H13Ax3.3009
O3···C13.580 (3)C17···H14Bii3.1314
O3···C32.872 (3)C17···H15Cxii2.9258
O4···C132.788 (3)C18···H11Axii3.3525
O4···C232.679 (4)C18···H12Bxii3.5459
O5···N12.649 (3)C18···H13Ax2.9809
O5···C13.000 (3)C18···H14Bii3.1837
O5···C93.113 (3)C18···H15Cxii3.1156
O5···C152.850 (3)C19···H11Axii3.5303
N1···C32.862 (3)C19···H12Bxii3.1146
N1···C162.862 (3)C19···H15Cxii3.3449
N1···C223.053 (3)C19···H16Avii3.3374
N2···C152.818 (4)C19···H18Ax3.5463
C1···C82.765 (3)C19···H19Bx3.3639
C1···C143.285 (4)C19···H20Cx3.3479
C1···C163.485 (3)C20···H4iv3.4608
C1···C203.269 (3)C20···H6vii3.3943
C2···C92.834 (3)C20···H15Cxii3.2647
C4···C72.791 (4)C21···H12Bxii3.4887
C5···C92.773 (3)C21···H15Cxii3.4265
C6···C82.794 (3)C21···H17Bvi3.4823
C7···C143.482 (3)C22···H5vi3.5442
C7···C152.828 (3)C22···H6vi3.3471
C7···C203.422 (4)C22···H10vii3.5672
C9···C143.346 (4)C23···H10vii3.5622
C9···C163.450 (4)C23···H12Bv2.9250
C9···C203.286 (4)C23···H19Bv3.5003
C13···C193.581 (4)C23···H20Cxiii3.4856
C13···C202.740 (3)C24···H10iii2.7110
C14···C212.773 (3)C24···H17Bxiii3.4851
C16···C192.792 (4)C24···H19Bv3.1740
C17···C212.805 (3)C24···H20Cxiii3.4241
C18···C202.805 (3)H1···N2vii2.7418
O1···C12i3.487 (4)H1···C6iv3.4832
O1···C17ii3.440 (3)H1···C13vii3.0655
O1···C18iii3.285 (3)H1···H4iv3.3676
O2···C4iv3.419 (3)H1···H6vii2.7266
O2···C5iv3.400 (3)H1···H20Cv3.4058
O2···C23v3.424 (3)H2···O3viii3.5373
O2···C24iv3.366 (3)H2···C6ix3.3689
O2···C24v3.378 (3)H2···C7ix3.3674
O3···C17ii3.552 (3)H2···C11viii3.3478
O4···N2vi3.526 (3)H2···C12i3.5014
O4···C7vi3.363 (3)H2···C16ix3.5155
O4···C13vi3.256 (3)H2···H7ix3.0777
O4···C14vi3.366 (3)H2···H11Aviii2.4907
O4···C19vii3.506 (3)H2···H14Bi3.2824
N2···O4vi3.526 (3)H2···H15Ci2.9882
N2···C1vii3.579 (3)H3···C2viii3.3558
N2···C14vii3.324 (3)H3···C8ix3.3698
N2···C15vii3.570 (3)H3···C9ix3.4764
C1···N2vii3.579 (3)H3···C10viii3.2903
C4···O2viii3.419 (3)H3···C16ix3.2503
C4···C5ix3.444 (3)H3···H3xiv3.2050
C4···C6ix3.445 (3)H3···H7viii3.4521
C5···O2viii3.400 (3)H3···H7ix2.3788
C5···C4ix3.444 (3)H3···H8ix3.5271
C5···C8ix3.362 (3)H4···O1ix3.3409
C5···C10viii3.414 (3)H4···C1viii3.5997
C6···C4ix3.445 (3)H4···C3ix3.5833
C6···C16viii3.550 (3)H4···C16viii2.6347
C7···O4vi3.363 (3)H4···C17viii2.8881
C8···C5ix3.362 (3)H4···C20viii3.4608
C10···C5iv3.414 (3)H4···H1viii3.3676
C12···O1i3.487 (4)H4···H6vi3.2171
C13···O4vi3.256 (3)H4···H7viii2.4759
C13···C13vii3.585 (3)H4···H8viii2.9084
C13···C14vii3.524 (3)H4···H13Axii3.5528
C13···C15vii3.527 (3)H5···O4vi2.4848
C13···C22vi3.422 (3)H5···C13vi3.5802
C14···O4vi3.366 (3)H5···C22vi3.5442
C14···N2vii3.324 (3)H5···H6vi2.7225
C14···C13vii3.524 (3)H5···H13Axii3.0760
C14···C21vii3.591 (3)H5···H15Cxii3.2508
C15···N2vii3.570 (3)H6···O4vi3.5171
C15···C13vii3.527 (3)H6···C1vii3.5653
C16···C6iv3.550 (3)H6···C6vi3.3152
C17···O1ii3.440 (3)H6···C7vi3.0373
C17···O3ii3.552 (3)H6···C15vii3.4641
C18···O1x3.285 (3)H6···C20vii3.3943
C19···O4vii3.506 (3)H6···C22vi3.3471
C19···C22vii3.548 (3)H6···H1vii2.7266
C21···C14vii3.591 (3)H6···H4vi3.2171
C21···C22vii3.530 (3)H6···H5vi2.7225
C22···C13vi3.422 (3)H6···H17Bvi3.5016
C22···C19vii3.548 (3)H7···C4ix3.4854
C22···C21vii3.530 (3)H7···C5ix3.1398
C23···O2v3.424 (3)H7···C6iv3.3133
C24···O2viii3.366 (3)H7···H2ix3.0777
C24···O2v3.378 (3)H7···H3iv3.4521
O1···H22.5024H7···H3ix2.3788
O2···H12.3541H7···H4iv2.4759
O2···H11A2.8600H7···H15Cxii3.4211
O2···H12B2.4509H8···O1ii2.6034
O3···H13A2.6002H8···O3ii2.6912
O3···H14B2.5486H8···C3ii3.3404
O3···H15C3.2399H8···C10ii3.5754
O4···H62.4392H8···C11ii3.3825
O4···H16A2.6354H8···C12ii3.4407
O4···H17B2.6916H8···H3ix3.5271
O5···H13.2272H8···H4iv2.9084
O5···H18A2.6002H8···H11Aii3.3950
O5···H19B2.5194H8···H13Ax3.2930
O5···H20C3.2261H8···H14Bii2.7242
N1···H52.6148H8···H15Cxii3.3256
N1···H72.5433H9···O1x2.4059
N2···H102.5667H9···O3x2.9268
C1···H73.0427H9···C3x3.2308
C1···H19B3.4704H9···C12x3.3470
C2···H19B3.2896H9···H11Axii3.2888
C3···H13.3018H9···H13Ax2.7331
C3···H22.6493H9···H14Bx3.2979
C3···H18A3.4876H9···H14Bii2.8269
C3···H19B3.5909H9···H16Avii3.5282
C4···H43.2566H10···O5vii3.4783
C5···H53.2740H10···C22vii3.5672
C6···H23.2599H10···C23vii3.5622
C7···H33.2681H10···C24x2.7110
C7···H73.4234H10···H11Axii3.5777
C8···H33.2732H10···H12Bxii3.0917
C8···H53.2941H10···H16Avii2.8818
C8···H18A3.3630H10···H17Bvi3.5483
C9···H13.2388H10···H18Ax2.7485
C9···H23.2679H10···H19Bx2.4185
C9···H43.2564H10···H20Cx2.5150
C9···H72.9583H11A···O1iv3.2773
C10···H12.4837H11A···C4iv3.0440
C10···H11A2.7433H11A···C12xi3.5332
C10···H12B2.5328H11A···C18xv3.3525
C14···H13.2488H11A···C19xv3.5303
C14···H52.9872H11A···H2iv2.4907
C15···H12.5425H11A···H8ii3.3950
C15···H52.4890H11A···H9xv3.2888
C15···H63.2376H11A···H10xv3.5777
C15···H72.6946H11A···H14Bxi2.9576
C16···H53.4501H11A···H15Cxi3.2071
C16···H93.2684H11A···H18Aiv3.4247
C17···H103.2702H12B···O4v3.5621
C18···H73.2742H12B···C18xv3.5459
C19···H83.2649H12B···C19xv3.1146
C20···H13.2870H12B···C21xv3.4887
C20···H52.9435H12B···C23v2.9250
C20···H83.2797H12B···H10xv3.0917
C20···H103.2989H12B···H16Av2.4860
C21···H63.1519H12B···H17Bv2.4932
C21···H73.3053H12B···H18Aiv2.9489
C21···H93.2729H12B···H20Civ3.4795
C22···H62.5672H13A···O1i3.4433
C22···H16A2.6191H13A···O4v2.8541
C22···H17B2.6478H13A···C17iii3.3009
H1···H73.3618H13A···C18iii2.9809
H2···H32.3180H13A···H4xv3.5528
H3···H42.3455H13A···H5xv3.0760
H4···H52.3310H13A···H8iii3.2930
H5···H73.4322H13A···H9iii2.7331
H7···H82.3115H13A···H16Av3.1643
H8···H92.3664H14B···O1i2.8415
H9···H102.3060H14B···C17ii3.1314
H11A···H13A2.8577H14B···C18ii3.1837
H11A···H14B2.3845H14B···H2i3.2824
H11A···H15C2.3470H14B···H8ii2.7242
H12B···H13A2.3474H14B···H9iii3.2979
H12B···H14B2.8576H14B···H9ii2.8269
H12B···H15C2.3843H14B···H11Axi2.9576
H16A···H18A2.8558H14B···H14Bxi3.4237
H16A···H19B2.3937H14B···H15Cxi3.2436
H16A···H20C2.3365H15C···C16xv2.9958
H17B···H18A2.3357H15C···C17xv2.9258
H17B···H19B2.8557H15C···C18xv3.1156
H17B···H20C2.3946H15C···C19xv3.3449
O1···H4ix3.3409H15C···C20xv3.2647
O1···H8ii2.6034H15C···C21xv3.4265
O1···H9iii2.4059H15C···H2i2.9882
O1···H11Aviii3.2773H15C···H5xv3.2508
O1···H13Ai3.4433H15C···H7xv3.4211
O1···H14Bi2.8415H15C···H8xv3.3256
O2···H16Av2.9985H15C···H11Axi3.2071
O2···H17Biv3.4220H15C···H14Bxi3.2436
O2···H17Bv3.4154H16A···O2v2.9985
O2···H18Aiv2.5154H16A···O3v2.9902
O2···H20Civ3.5896H16A···C10v2.9668
O2···H20Cv2.5977H16A···C11v3.0820
O3···H2iv3.5373H16A···C19vii3.3374
O3···H8ii2.6912H16A···H9vii3.5282
O3···H9iii2.9268H16A···H10vii2.8818
O3···H16Av2.9902H16A···H12Bv2.4860
O4···H5vi2.4848H16A···H13Av3.1643
O4···H6vi3.5171H16A···H19Bv3.0400
O4···H12Bv3.5621H17B···O2viii3.4220
O4···H13Av2.8541H17B···O2v3.4154
O5···H10vii3.4783H17B···N2vi2.8767
N2···H1vii2.7418H17B···C11v3.4166
N2···H17Bvi2.8767H17B···C13vi3.4118
N2···H20Cx3.3870H17B···C21vi3.4823
C1···H4iv3.5997H17B···C24xiii3.4851
C1···H6vii3.5653H17B···H6vi3.5016
C2···H3iv3.3558H17B···H10vi3.5483
C3···H4ix3.5833H17B···H12Bv2.4932
C3···H8ii3.3404H17B···H18Axiii3.3506
C3···H9iii3.2308H17B···H20Cxiii2.7540
C4···H7ix3.4854H18A···O2viii2.5154
C4···H11Aviii3.0440H18A···C11viii3.5891
C5···H7ix3.1398H18A···C19iii3.5463
C6···H1viii3.4832H18A···H10iii2.7485
C6···H2ix3.3689H18A···H11Aviii3.4247
C6···H6vi3.3152H18A···H12Bviii2.9489
C6···H7viii3.3133H18A···H17Bxiii3.3506
C7···H2ix3.3674H18A···H20Cxiii3.2218
C7···H6vi3.0373H19B···C19iii3.3639
C8···H3ix3.3698H19B···C23v3.5003
C9···H3ix3.4764H19B···C24v3.1740
C10···H3iv3.2903H19B···H10iii2.4185
C10···H8ii3.5754H19B···H16Av3.0400
C10···H16Av2.9668H19B···H19Bv2.4826
C10···H20Cv3.2797H19B···H20Cv3.2698
C11···H2iv3.3478H20C···O2viii3.5896
C11···H8ii3.3825H20C···O2v2.5977
C11···H16Av3.0820H20C···N2iii3.3870
C11···H17Bv3.4166H20C···C10v3.2797
C11···H18Aiv3.5891H20C···C19iii3.3479
C12···H2i3.5014H20C···C23xiii3.4856
C12···H8ii3.4407H20C···C24xiii3.4241
C12···H9iii3.3470H20C···H1v3.4058
C12···H11Axi3.5332H20C···H10iii2.5150
C13···H1vii3.0655H20C···H12Bviii3.4795
C13···H5vi3.5802H20C···H17Bxiii2.7540
C13···H17Bvi3.4118H20C···H18Axiii3.2218
C15···H6vii3.4641H20C···H19Bv3.2698
C16···H2ix3.5155H20C···H20Cxiii3.0947
C10—O3—C11116.03 (17)O4—C22—C14122.8 (2)
C22—O5—C23116.67 (17)O5—C22—C14113.12 (18)
C1—N1—C9120.57 (19)O5—C23—C24106.50 (18)
C1—N1—C15119.36 (17)N1—C1—H1118.012
C9—N1—C15120.07 (15)C2—C1—H1118.004
C13—N2—C21117.3 (2)C5—C4—H2119.617
N1—C1—C2123.98 (18)C8—C4—H2119.625
C1—C2—C3120.06 (16)C4—C5—H3119.978
C1—C2—C10114.17 (18)C6—C5—H3119.971
C3—C2—C10125.77 (19)C5—C6—H4119.697
O1—C3—C2125.66 (17)C7—C6—H4119.692
O1—C3—C8119.87 (18)C6—C7—H5120.452
C2—C3—C8114.47 (19)C9—C7—H5120.455
C5—C4—C8120.8 (2)O3—C11—H11A110.326
C4—C5—C6120.1 (2)O3—C11—H12B110.317
C5—C6—C7120.61 (18)C12—C11—H11A110.316
C6—C7—C9119.1 (2)C12—C11—H12B110.320
C3—C8—C4119.6 (2)H11A—C11—H12B108.569
C3—C8—C9122.01 (18)C11—C12—H13A109.471
C4—C8—C9118.38 (17)C11—C12—H14B109.471
N1—C9—C7120.1 (2)C11—C12—H15C109.470
N1—C9—C8118.82 (16)H13A—C12—H14B109.471
C7—C9—C8121.09 (19)H13A—C12—H15C109.466
O2—C10—O3123.53 (17)H14B—C12—H15C109.479
O2—C10—C2123.3 (2)N2—C13—H6117.274
O3—C10—C2113.22 (18)C14—C13—H6117.275
O3—C11—C12106.99 (18)C17—C16—H7119.663
N2—C13—C14125.5 (2)C20—C16—H7119.668
C13—C14—C15116.96 (19)C16—C17—H8119.901
C13—C14—C22116.01 (18)C18—C17—H8119.897
C15—C14—C22127.0 (2)C17—C18—H9119.931
N1—C15—C14122.56 (18)C19—C18—H9119.919
N1—C15—C20117.19 (18)C18—C19—H10119.481
C14—C15—C20120.3 (2)C21—C19—H10119.469
C17—C16—C20120.7 (3)O5—C23—H16A110.426
C16—C17—C18120.2 (2)O5—C23—H17B110.425
C17—C18—C19120.1 (2)C24—C23—H16A110.425
C18—C19—C21121.1 (3)C24—C23—H17B110.428
C15—C20—C16123.4 (2)H16A—C23—H17B108.636
C15—C20—C21117.64 (18)C23—C24—H18A109.469
C16—C20—C21118.91 (18)C23—C24—H19B109.467
N2—C21—C19118.7 (2)C23—C24—H20C109.462
N2—C21—C20122.31 (18)H18A—C24—H19B109.476
C19—C21—C20119.01 (19)H18A—C24—H20C109.473
O4—C22—O5124.09 (19)H19B—C24—H20C109.480
C10—O3—C11—C12163.33 (14)C3—C8—C9—N11.7 (3)
C10—O3—C11—H11A76.6C3—C8—C9—C7177.41 (14)
C10—O3—C11—H12B43.3C4—C8—C9—N1179.99 (15)
C11—O3—C10—O21.9 (3)C4—C8—C9—C70.9 (3)
C11—O3—C10—C2178.65 (13)O3—C11—C12—H13A63.4
C22—O5—C23—C24177.74 (14)O3—C11—C12—H14B56.6
C22—O5—C23—H16A57.8O3—C11—C12—H15C176.6
C22—O5—C23—H17B62.3H11A—C11—C12—H13A176.6
C23—O5—C22—O40.3 (3)H11A—C11—C12—H14B63.4
C23—O5—C22—C14179.11 (13)H11A—C11—C12—H15C56.6
C1—N1—C9—C7179.62 (14)H12B—C11—C12—H13A56.6
C1—N1—C9—C81.3 (3)H12B—C11—C12—H14B176.6
C9—N1—C1—C22.6 (3)H12B—C11—C12—H15C63.4
C9—N1—C1—H1177.4N2—C13—C14—C150.1 (3)
C1—N1—C15—C1488.7 (2)N2—C13—C14—C22179.21 (15)
C1—N1—C15—C2092.14 (18)H6—C13—C14—C15179.9
C15—N1—C1—C2178.02 (14)H6—C13—C14—C220.8
C15—N1—C1—H12.0C13—C14—C15—N1179.07 (14)
C9—N1—C15—C1490.68 (19)C13—C14—C15—C201.8 (3)
C9—N1—C15—C2088.5 (2)C13—C14—C22—O46.1 (3)
C15—N1—C9—C70.2 (3)C13—C14—C22—O5174.47 (14)
C15—N1—C9—C8179.35 (14)C15—C14—C22—O4173.10 (16)
C13—N2—C21—C19179.53 (15)C15—C14—C22—O56.3 (3)
C13—N2—C21—C200.3 (3)C22—C14—C15—N11.7 (3)
C21—N2—C13—C140.9 (3)C22—C14—C15—C20177.43 (15)
C21—N2—C13—H6179.0N1—C15—C20—C161.1 (3)
N1—C1—C2—C30.8 (3)N1—C15—C20—C21178.46 (13)
N1—C1—C2—C10178.65 (15)C14—C15—C20—C16178.09 (15)
H1—C1—C2—C3179.2C14—C15—C20—C212.4 (3)
H1—C1—C2—C101.3C17—C16—C20—C15178.37 (15)
C1—C2—C3—O1178.32 (16)C17—C16—C20—C211.2 (3)
C1—C2—C3—C82.0 (3)C20—C16—C17—C180.7 (3)
C1—C2—C10—O24.8 (3)C20—C16—C17—H8179.3
C1—C2—C10—O3175.71 (15)H7—C16—C17—C18179.3
C3—C2—C10—O2175.77 (16)H7—C16—C17—H80.7
C3—C2—C10—O33.7 (3)H7—C16—C20—C151.6
C10—C2—C3—O11.1 (3)H7—C16—C20—C21178.8
C10—C2—C3—C8178.61 (15)C16—C17—C18—C190.3 (3)
O1—C3—C8—C41.2 (3)C16—C17—C18—H9179.7
O1—C3—C8—C9177.06 (15)H8—C17—C18—C19179.7
C2—C3—C8—C4178.49 (14)H8—C17—C18—H90.3
C2—C3—C8—C93.2 (3)C17—C18—C19—C210.7 (3)
C5—C4—C8—C3178.51 (15)C17—C18—C19—H10179.3
C5—C4—C8—C90.2 (3)H9—C18—C19—C21179.2
C8—C4—C5—C61.0 (3)H9—C18—C19—H100.8
C8—C4—C5—H3178.9C18—C19—C21—N2179.92 (16)
H2—C4—C5—C6179.0C18—C19—C21—C200.2 (3)
H2—C4—C5—H31.0H10—C19—C21—N20.1
H2—C4—C8—C31.5H10—C19—C21—C20179.8
H2—C4—C8—C9179.8C15—C20—C21—N21.3 (3)
C4—C5—C6—C70.9 (3)C15—C20—C21—C19178.85 (14)
C4—C5—C6—H4179.1C16—C20—C21—N2179.13 (14)
H3—C5—C6—C7179.1C16—C20—C21—C190.7 (3)
H3—C5—C6—H40.9O5—C23—C24—H18A65.3
C5—C6—C7—C90.1 (3)O5—C23—C24—H19B54.7
C5—C6—C7—H5179.9O5—C23—C24—H20C174.7
H4—C6—C7—C9179.9H16A—C23—C24—H18A174.8
H4—C6—C7—H50.1H16A—C23—C24—H19B65.2
C6—C7—C9—N1179.86 (15)H16A—C23—C24—H20C54.8
C6—C7—C9—C81.0 (3)H17B—C23—C24—H18A54.6
H5—C7—C9—N10.1H17B—C23—C24—H19B174.6
H5—C7—C9—C8179.0H17B—C23—C24—H20C65.4
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) x1, y, z; (ix) x, y, z; (x) x, y1, z; (xi) x+2, y+1, z; (xii) x1, y1, z; (xiii) x, y+1, z+1; (xiv) x1, y, z; (xv) x+1, y+1, z.

Experimental details

Crystal data
Chemical formulaC24H20N2O5
Mr416.43
Crystal system, space groupTriclinic, 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)
V3)973.5 (6)
Z2
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.25 × 0.20 × 0.15
Data collection
DiffractometerRigaku AFC-7R
diffractometer
Absorption correction
No. of measured, independent and
observed [F2 > 2σ(F2)] reflections
5486, 4479, 3077
Rint0.034
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.052, 0.159, 1.02
No. of reflections4479
No. of parameters282
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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

First citationBurla, 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
First citationIshikawa, Y. & Fujii, S. (2011). Bioinformation, 6, 221–225.  CrossRef PubMed
First citationKajihara, S. (1965). Nippon Kagaku Zasshi, 86, 933–941.  CrossRef CAS
First citationRigaku (1999). WinAFC Diffractometer Control Software. Rigaku Corporation, Tokyo, Japan.
First citationRigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals

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