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ISSN: 2056-9890

Di­ethyl 3,3′-(phenyl­methyl­ene)bis­­(1H-indole-2-carboxyl­ate)

aChemical Engineering Department, Nanjing College of Chemical Technology, Nanjing 210048, People's Republic of China
*Correspondence e-mail: njutshs@126.com

(Received 18 August 2012; accepted 19 August 2012; online 25 August 2012)

In the title compound, C29H26N2O4, the benzene ring is twisted by 73.5 (5) and 84.9 (3)° with respect to the mean planes of the two indole ring systems; the mean planes of the indole ring systems are oriented at a dihedral angle of 82.0 (5)°. In the crystal, mol­ecules are linked by pairs of N—H⋯O hydrogen bonds into chains.

Related literature

For applications of indole derivatives, see: Poter et al. (1977[Poter, J. K., Bacon, C. W., Robins, J. D., Himmelsbach, D. S. & Higman, H. C. (1977). J. Agric. Food Chem. 25, 88-93.]); Sundberg (1996[Sundberg, R. J. (1996). The Chemistry of Indoles, p. 113. New York: Academic Press.]); Chang et al. (1999[Chang, Y. C., Riby, J., Grace, H. F., Peng, G. F. & Bieldanes, L. F. (1999). Biochem. Pharmacol. 58, 825-834.]); Ge et al. (1999[Ge, X., Fares, F. A. & Fares, S. Y. (1999). Anticancer Res. 19, 3199-3203.]); Ni (2008[Ni, Y.-C. (2008). Curr. Med. Imaging Rev. 4, 96-112.]).

[Scheme 1]

Experimental

Crystal data
  • C29H26N2O4

  • Mr = 466.52

  • Triclinic, [P \overline 1]

  • a = 8.7340 (17) Å

  • b = 9.871 (2) Å

  • c = 15.000 (3) Å

  • α = 76.14 (3)°

  • β = 83.91 (3)°

  • γ = 83.09 (3)°

  • V = 1242.4 (4) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 293 K

  • 0.30 × 0.20 × 0.10 mm

Data collection
  • Enraf–Nonius CAD-4 diffractometer

  • 4879 measured reflections

  • 4557 independent reflections

  • 2813 reflections with I > 2σ(I)

  • Rint = 0.032

  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement
  • R[F2 > 2σ(F2)] = 0.059

  • wR(F2) = 0.144

  • S = 1.00

  • 4557 reflections

  • 316 parameters

  • 2 restraints

  • H-atom parameters constrained

  • Δρmax = 0.33 e Å−3

  • Δρmin = −0.24 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1A⋯O2i 0.86 2.21 2.955 (3) 144
N2—H2A⋯O4ii 0.86 2.07 2.880 (3) 157
Symmetry codes: (i) -x, -y+2, -z+1; (ii) -x+1, -y+1, -z+2.

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994[Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Indole derivatives are found abundantly in a variety of natural plants and exhibit various physiological properties (Poter et al., 1977; Sundberg, 1996). Among them, bis-indolymethane derivatives are found to be kinds of potentially bioactive compounds (Chang et al., 1999; Ge et al., 1999). In recent years, the synthesis and application of bis-indolymethane derivatives have been widely studied. The title compound is one of bis-indolymethane derivatives as a precursor for MRI Contrast Agents (Ni, 2008). We report here its crystal structure.

The molecular structure of the title compound is shown in Fig. 1. The benzene ring is twisted to the two indole rings with the dihedral angles of 73.5 (5) and 84.9 (3)°, respectively. Two indole rings make a dihedral angle of 82.0 (5)° to each other.

As shown in Figure 2, the molecules are linked by paired N—H···O hydrogen bonds into dimers in the crystal lattice. The structural parameters for the intermolecular hydrogen bonds resulting in the formation of dimers are given in Table 1.

Related literature top

For applications of indole derivatives, see: Poter et al. (1977); Sundberg (1996); Chang et al. (1999); Ge et al. (1999); Ni (2008).

Experimental top

Ethyl indole-2-carboxylate (18.9 g, 100 mmol) was dissolved in 200 ml ethanol; commercially available benzaldehyde (5.3 g, 50 mmol) was added and the mixture was heated to reflux temperature. Concentrated HCl (3.7 ml) was added and the reaction was left for 1 h. After cooling the white product was filtered off and washed thoroughly with ethanol. The reaction can be followed by TLC (CHCl3:hexane = 1:1). Yield was 90%. Crystals of the title compound suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution.

Refinement top

H atoms were positioned geometrically, with N— H = 0.86 Å and C—H = 0.93, 0.96, 0.97 and 0.98 Å for aromatic, methyl, methylene and methine H, respectively, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C,N), where x = 1.5 for methyl H, and x = 1.2 for all other H atoms.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
Figure 1. The molecular structure of (I), showing the atom-numbering scheme and displacement ellipsoids at the 30% probability level.

Figure 2. A packing diagram of (I). Intermolecular hydrogen bonds are shown as dashed lines.
Diethyl 3,3'-(phenylmethylene)bis(1H-indole-2-carboxylate) top
Crystal data top
C29H26N2O4Z = 2
Mr = 466.52F(000) = 492
Triclinic, P1Dx = 1.247 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.7340 (17) ÅCell parameters from 25 reflections
b = 9.871 (2) Åθ = 9–13°
c = 15.000 (3) ŵ = 0.08 mm1
α = 76.14 (3)°T = 293 K
β = 83.91 (3)°Block, colorless
γ = 83.09 (3)°0.30 × 0.20 × 0.10 mm
V = 1242.4 (4) Å3
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.032
Radiation source: fine-focus sealed tubeθmax = 25.4°, θmin = 1.4°
Graphite monochromatorh = 010
ω/2θ scansk = 1111
4879 measured reflectionsl = 1718
4557 independent reflections3 standard reflections every 200 reflections
2813 reflections with I > 2σ(I) intensity decay: 1%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.068P)2]
where P = (Fo2 + 2Fc2)/3
4557 reflections(Δ/σ)max < 0.001
316 parametersΔρmax = 0.33 e Å3
2 restraintsΔρmin = 0.24 e Å3
Crystal data top
C29H26N2O4γ = 83.09 (3)°
Mr = 466.52V = 1242.4 (4) Å3
Triclinic, P1Z = 2
a = 8.7340 (17) ÅMo Kα radiation
b = 9.871 (2) ŵ = 0.08 mm1
c = 15.000 (3) ÅT = 293 K
α = 76.14 (3)°0.30 × 0.20 × 0.10 mm
β = 83.91 (3)°
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.032
4879 measured reflections3 standard reflections every 200 reflections
4557 independent reflections intensity decay: 1%
2813 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0592 restraints
wR(F2) = 0.144H-atom parameters constrained
S = 1.00Δρmax = 0.33 e Å3
4557 reflectionsΔρmin = 0.24 e Å3
316 parameters
Special details top

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.1091 (2)1.1102 (2)0.57403 (13)0.0464 (5)
H1A0.05621.10300.53050.056*
O10.3652 (2)0.79594 (18)0.61548 (14)0.0671 (6)
C10.0036 (3)1.3484 (3)0.59245 (18)0.0543 (7)
H1B0.06531.36540.54690.065*
N20.3177 (2)0.6564 (2)0.93548 (13)0.0455 (5)
H2A0.34530.57600.97000.055*
O20.1783 (2)0.8636 (2)0.51907 (13)0.0684 (6)
C20.0155 (3)1.4450 (3)0.64135 (19)0.0622 (8)
H2B0.04491.53050.62830.075*
O30.65528 (18)0.75379 (17)0.78745 (11)0.0501 (5)
C30.1166 (3)1.4189 (3)0.71086 (19)0.0617 (8)
H3A0.12141.48720.74350.074*
O40.6289 (2)0.57275 (18)0.90776 (13)0.0650 (6)
C40.2091 (3)1.2949 (3)0.73230 (18)0.0556 (7)
H4A0.27531.27890.77910.067*
C50.2020 (3)1.1927 (2)0.68248 (15)0.0408 (6)
C60.0979 (3)1.2226 (3)0.61280 (16)0.0451 (6)
C70.2770 (3)1.0539 (2)0.68458 (15)0.0384 (6)
C80.2186 (3)1.0099 (2)0.61581 (15)0.0402 (6)
C90.2502 (3)0.8841 (3)0.57918 (18)0.0491 (6)
C100.4101 (4)0.6726 (3)0.5781 (3)0.0934 (12)
H10A0.33480.60540.60160.112*
H10B0.40810.69960.51160.112*
C110.5551 (5)0.6089 (5)0.5996 (4)0.1460 (19)
H11A0.57810.52850.57330.219*
H11B0.55750.58000.66530.219*
H11C0.63080.67400.57520.219*
C120.3962 (3)0.9705 (2)0.74867 (15)0.0373 (6)
H12A0.47080.92170.71060.045*
C130.4886 (3)1.0644 (2)0.78505 (16)0.0395 (6)
C140.6008 (3)1.1351 (3)0.72766 (19)0.0568 (7)
H14A0.62441.12020.66860.068*
C150.6790 (4)1.2282 (3)0.7569 (3)0.0764 (9)
H15A0.75411.27590.71700.092*
C160.6473 (4)1.2511 (3)0.8438 (2)0.0710 (9)
H16A0.69911.31540.86240.085*
C170.5397 (3)1.1794 (3)0.9029 (2)0.0611 (8)
H17A0.51901.19340.96230.073*
C180.4605 (3)1.0849 (3)0.87424 (17)0.0478 (6)
H18A0.38821.03500.91510.057*
C190.3294 (3)0.8562 (2)0.82476 (15)0.0374 (6)
C200.1766 (3)0.8539 (2)0.87173 (15)0.0395 (6)
C210.0399 (3)0.9474 (3)0.86615 (18)0.0511 (7)
H21A0.03631.03220.82260.061*
C220.0862 (3)0.9119 (3)0.92517 (19)0.0619 (8)
H22A0.17570.97380.92140.074*
C230.0847 (3)0.7852 (3)0.9912 (2)0.0632 (8)
H23A0.17340.76421.02980.076*
C240.0448 (3)0.6912 (3)1.00012 (17)0.0527 (7)
H24A0.04640.60711.04430.063*
C250.1743 (3)0.7277 (2)0.93981 (16)0.0426 (6)
C260.4107 (3)0.7330 (2)0.86766 (15)0.0388 (6)
C270.5734 (3)0.6772 (2)0.85723 (16)0.0402 (6)
C280.8177 (3)0.7041 (3)0.77442 (18)0.0553 (7)
H28A0.82820.61020.76380.066*
H28B0.87010.70190.82870.066*
C290.8863 (3)0.8028 (3)0.6932 (2)0.0802 (10)
H29A0.99400.77270.68250.120*
H29B0.87590.89520.70480.120*
H29C0.83350.80440.64000.120*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0488 (13)0.0511 (13)0.0378 (11)0.0003 (10)0.0143 (10)0.0049 (10)
O10.0723 (14)0.0525 (12)0.0859 (14)0.0166 (10)0.0364 (11)0.0322 (10)
C10.0510 (16)0.0538 (17)0.0462 (15)0.0093 (13)0.0099 (13)0.0071 (13)
N20.0469 (13)0.0359 (11)0.0461 (12)0.0014 (10)0.0069 (10)0.0039 (9)
O20.0705 (13)0.0795 (14)0.0662 (13)0.0077 (11)0.0280 (11)0.0355 (11)
C20.067 (2)0.0520 (17)0.0555 (18)0.0173 (15)0.0037 (15)0.0005 (15)
O30.0440 (10)0.0501 (10)0.0468 (10)0.0059 (8)0.0009 (8)0.0007 (8)
C30.076 (2)0.0451 (16)0.0604 (18)0.0116 (15)0.0099 (16)0.0114 (13)
O40.0580 (12)0.0507 (11)0.0675 (12)0.0134 (9)0.0037 (10)0.0132 (10)
C40.0693 (19)0.0456 (16)0.0508 (16)0.0055 (14)0.0184 (14)0.0086 (13)
C50.0446 (14)0.0399 (14)0.0320 (13)0.0002 (11)0.0026 (11)0.0008 (11)
C60.0468 (15)0.0456 (15)0.0356 (14)0.0011 (12)0.0037 (11)0.0032 (11)
C70.0397 (13)0.0400 (13)0.0317 (12)0.0015 (11)0.0049 (11)0.0030 (10)
C80.0442 (14)0.0384 (13)0.0361 (13)0.0003 (11)0.0100 (11)0.0040 (11)
C90.0489 (16)0.0536 (16)0.0442 (15)0.0016 (13)0.0104 (13)0.0088 (13)
C100.098 (3)0.060 (2)0.138 (3)0.0167 (19)0.046 (2)0.050 (2)
C110.123 (4)0.135 (4)0.200 (5)0.021 (3)0.042 (4)0.082 (4)
C120.0407 (14)0.0348 (13)0.0353 (13)0.0057 (11)0.0102 (11)0.0073 (10)
C130.0398 (14)0.0362 (13)0.0390 (14)0.0037 (11)0.0102 (11)0.0026 (11)
C140.0574 (17)0.0537 (17)0.0561 (17)0.0123 (14)0.0014 (14)0.0055 (14)
C150.069 (2)0.0589 (19)0.097 (3)0.0266 (17)0.0001 (19)0.0023 (18)
C160.074 (2)0.0601 (19)0.085 (2)0.0156 (17)0.0234 (19)0.0172 (18)
C170.074 (2)0.0598 (18)0.0549 (17)0.0035 (16)0.0240 (16)0.0178 (15)
C180.0524 (16)0.0494 (15)0.0412 (15)0.0021 (13)0.0084 (12)0.0090 (12)
C190.0405 (14)0.0338 (13)0.0363 (13)0.0004 (11)0.0105 (11)0.0036 (10)
C200.0413 (14)0.0376 (13)0.0379 (13)0.0032 (11)0.0069 (11)0.0042 (10)
C210.0479 (16)0.0469 (15)0.0527 (16)0.0056 (13)0.0080 (13)0.0034 (12)
C220.0407 (16)0.0669 (19)0.070 (2)0.0074 (14)0.0033 (15)0.0103 (16)
C230.0467 (17)0.071 (2)0.0633 (19)0.0068 (15)0.0103 (14)0.0054 (16)
C240.0485 (16)0.0557 (17)0.0483 (16)0.0087 (14)0.0017 (13)0.0004 (13)
C250.0413 (14)0.0420 (14)0.0442 (14)0.0024 (12)0.0085 (12)0.0080 (11)
C260.0444 (14)0.0343 (13)0.0343 (13)0.0017 (11)0.0066 (11)0.0023 (10)
C270.0447 (15)0.0333 (13)0.0382 (13)0.0012 (11)0.0054 (12)0.0014 (11)
C280.0501 (17)0.0554 (17)0.0543 (17)0.0047 (13)0.0025 (13)0.0084 (13)
C290.065 (2)0.082 (2)0.088 (2)0.0115 (18)0.0150 (18)0.0142 (19)
Geometric parameters (Å, º) top
N1—C61.361 (3)C12—C131.524 (3)
N1—C81.375 (3)C12—H12A0.9800
N1—H1A0.8600C13—C141.374 (3)
O1—C91.320 (3)C13—C181.392 (3)
O1—C101.455 (3)C14—C151.382 (4)
C1—C21.354 (4)C14—H14A0.9300
C1—C61.393 (3)C15—C161.370 (4)
C1—H1B0.9300C15—H15A0.9300
N2—C251.364 (3)C16—C171.362 (4)
N2—C261.368 (3)C16—H16A0.9300
N2—H2A0.8600C17—C181.394 (3)
O2—C91.219 (3)C17—H17A0.9300
C2—C31.394 (4)C18—H18A0.9300
C2—H2B0.9300C19—C261.382 (3)
O3—C271.331 (3)C19—C201.442 (3)
O3—C281.453 (3)C20—C251.410 (3)
C3—C41.372 (3)C20—C211.415 (3)
C3—H3A0.9300C21—C221.363 (3)
O4—C271.207 (3)C21—H21A0.9300
C4—C51.402 (3)C22—C231.397 (4)
C4—H4A0.9300C22—H22A0.9300
C5—C61.413 (3)C23—C241.371 (4)
C5—C71.440 (3)C23—H23A0.9300
C7—C81.375 (3)C24—C251.397 (3)
C7—C121.520 (3)C24—H24A0.9300
C8—C91.460 (3)C26—C271.467 (3)
C10—C111.379 (4)C28—C291.486 (4)
C10—H10A0.9700C28—H28A0.9700
C10—H10B0.9700C28—H28B0.9700
C11—H11A0.9600C29—H29A0.9600
C11—H11B0.9600C29—H29B0.9600
C11—H11C0.9600C29—H29C0.9600
C12—C191.522 (3)
C6—N1—C8108.91 (19)C18—C13—C12122.3 (2)
C6—N1—H1A125.5C13—C14—C15120.6 (3)
C8—N1—H1A125.5C13—C14—H14A119.7
C9—O1—C10117.3 (2)C15—C14—H14A119.7
C2—C1—C6117.7 (3)C16—C15—C14120.8 (3)
C2—C1—H1B121.2C16—C15—H15A119.6
C6—C1—H1B121.2C14—C15—H15A119.6
C25—N2—C26109.28 (19)C17—C16—C15119.7 (3)
C25—N2—H2A125.4C17—C16—H16A120.2
C26—N2—H2A125.4C15—C16—H16A120.2
C1—C2—C3121.4 (3)C16—C17—C18120.0 (3)
C1—C2—H2B119.3C16—C17—H17A120.0
C3—C2—H2B119.3C18—C17—H17A120.0
C27—O3—C28116.10 (19)C13—C18—C17120.6 (3)
C4—C3—C2121.6 (3)C13—C18—H18A119.7
C4—C3—H3A119.2C17—C18—H18A119.7
C2—C3—H3A119.2C26—C19—C20105.12 (19)
C3—C4—C5119.0 (2)C26—C19—C12125.5 (2)
C3—C4—H4A120.5C20—C19—C12129.27 (19)
C5—C4—H4A120.5C25—C20—C21117.3 (2)
C4—C5—C6117.8 (2)C25—C20—C19107.5 (2)
C4—C5—C7135.3 (2)C21—C20—C19135.2 (2)
C6—C5—C7106.9 (2)C22—C21—C20119.4 (2)
N1—C6—C1129.3 (2)C22—C21—H21A120.3
N1—C6—C5108.1 (2)C20—C21—H21A120.3
C1—C6—C5122.6 (2)C21—C22—C23121.8 (3)
C8—C7—C5105.8 (2)C21—C22—H22A119.1
C8—C7—C12126.1 (2)C23—C22—H22A119.1
C5—C7—C12128.1 (2)C24—C23—C22121.3 (3)
N1—C8—C7110.2 (2)C24—C23—H23A119.3
N1—C8—C9116.0 (2)C22—C23—H23A119.3
C7—C8—C9133.8 (2)C23—C24—C25116.9 (2)
O2—C9—O1122.9 (3)C23—C24—H24A121.5
O2—C9—C8122.9 (2)C25—C24—H24A121.5
O1—C9—C8114.2 (2)N2—C25—C24129.0 (2)
C11—C10—O1113.3 (3)N2—C25—C20107.6 (2)
C11—C10—H10A108.9C24—C25—C20123.3 (2)
O1—C10—H10A108.9N2—C26—C19110.4 (2)
C11—C10—H10B108.9N2—C26—C27117.0 (2)
O1—C10—H10B108.9C19—C26—C27132.5 (2)
H10A—C10—H10B107.7O4—C27—O3122.8 (2)
C10—C11—H11A109.5O4—C27—C26123.4 (2)
C10—C11—H11B109.5O3—C27—C26113.7 (2)
H11A—C11—H11B109.5O3—C28—C29107.3 (2)
C10—C11—H11C109.5O3—C28—H28A110.2
H11A—C11—H11C109.5C29—C28—H28A110.2
H11B—C11—H11C109.5O3—C28—H28B110.2
C7—C12—C19113.36 (18)C29—C28—H28B110.2
C7—C12—C13112.51 (18)H28A—C28—H28B108.5
C19—C12—C13112.78 (18)C28—C29—H29A109.5
C7—C12—H12A105.8C28—C29—H29B109.5
C19—C12—H12A105.8H29A—C29—H29B109.5
C13—C12—H12A105.8C28—C29—H29C109.5
C14—C13—C18118.2 (2)H29A—C29—H29C109.5
C14—C13—C12119.4 (2)H29B—C29—H29C109.5
C6—C1—C2—C31.2 (4)C13—C14—C15—C160.5 (5)
C1—C2—C3—C40.5 (4)C14—C15—C16—C171.3 (5)
C2—C3—C4—C50.4 (4)C15—C16—C17—C181.1 (4)
C3—C4—C5—C60.6 (4)C14—C13—C18—C172.8 (4)
C3—C4—C5—C7179.5 (3)C12—C13—C18—C17175.3 (2)
C8—N1—C6—C1179.6 (2)C16—C17—C18—C131.0 (4)
C8—N1—C6—C50.8 (3)C7—C12—C19—C26152.1 (2)
C2—C1—C6—N1179.6 (2)C13—C12—C19—C2678.6 (3)
C2—C1—C6—C50.9 (4)C7—C12—C19—C2032.3 (3)
C4—C5—C6—N1179.6 (2)C13—C12—C19—C2097.0 (3)
C7—C5—C6—N10.5 (3)C26—C19—C20—C250.8 (2)
C4—C5—C6—C10.0 (4)C12—C19—C20—C25177.0 (2)
C7—C5—C6—C1179.1 (2)C26—C19—C20—C21176.8 (3)
C4—C5—C7—C8179.5 (3)C12—C19—C20—C210.5 (4)
C6—C5—C7—C81.6 (2)C25—C20—C21—C220.5 (4)
C4—C5—C7—C120.6 (4)C19—C20—C21—C22177.8 (3)
C6—C5—C7—C12178.3 (2)C20—C21—C22—C230.2 (4)
C6—N1—C8—C71.9 (3)C21—C22—C23—C240.7 (5)
C6—N1—C8—C9177.3 (2)C22—C23—C24—C250.5 (4)
C5—C7—C8—N12.2 (3)C26—N2—C25—C24178.0 (2)
C12—C7—C8—N1177.8 (2)C26—N2—C25—C200.3 (3)
C5—C7—C8—C9176.9 (3)C23—C24—C25—N2177.9 (2)
C12—C7—C8—C93.2 (4)C23—C24—C25—C200.2 (4)
C10—O1—C9—O22.7 (4)C21—C20—C25—N2177.8 (2)
C10—O1—C9—C8176.1 (2)C19—C20—C25—N20.3 (3)
N1—C8—C9—O24.4 (4)C21—C20—C25—C240.7 (4)
C7—C8—C9—O2176.7 (3)C19—C20—C25—C24178.7 (2)
N1—C8—C9—O1174.4 (2)C25—N2—C26—C190.8 (3)
C7—C8—C9—O14.6 (4)C25—N2—C26—C27175.8 (2)
C9—O1—C10—C11162.2 (4)C20—C19—C26—N21.0 (3)
C8—C7—C12—C1976.6 (3)C12—C19—C26—N2177.4 (2)
C5—C7—C12—C19103.4 (3)C20—C19—C26—C27175.0 (2)
C8—C7—C12—C13154.0 (2)C12—C19—C26—C271.5 (4)
C5—C7—C12—C1326.1 (3)C28—O3—C27—O40.4 (3)
C7—C12—C13—C1474.5 (3)C28—O3—C27—C26179.4 (2)
C19—C12—C13—C14155.7 (2)N2—C26—C27—O43.8 (4)
C7—C12—C13—C18103.5 (2)C19—C26—C27—O4171.9 (3)
C19—C12—C13—C1826.2 (3)N2—C26—C27—O3177.19 (19)
C18—C13—C14—C152.5 (4)C19—C26—C27—O37.1 (4)
C12—C13—C14—C15175.6 (2)C27—O3—C28—C29179.4 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O2i0.862.212.955 (3)144
N2—H2A···O4ii0.862.072.880 (3)157
Symmetry codes: (i) x, y+2, z+1; (ii) x+1, y+1, z+2.

Experimental details

Crystal data
Chemical formulaC29H26N2O4
Mr466.52
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)8.7340 (17), 9.871 (2), 15.000 (3)
α, β, γ (°)76.14 (3), 83.91 (3), 83.09 (3)
V3)1242.4 (4)
Z2
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.30 × 0.20 × 0.10
Data collection
DiffractometerEnraf–Nonius CAD-4
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
4879, 4557, 2813
Rint0.032
(sin θ/λ)max1)0.603
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.059, 0.144, 1.00
No. of reflections4557
No. of parameters316
No. of restraints2
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.33, 0.24

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1995), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O2i0.862.212.955 (3)144
N2—H2A···O4ii0.862.072.880 (3)157
Symmetry codes: (i) x, y+2, z+1; (ii) x+1, y+1, z+2.
 

Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for assistance with the data collection.

References

First citationChang, Y. C., Riby, J., Grace, H. F., Peng, G. F. & Bieldanes, L. F. (1999). Biochem. Pharmacol. 58, 825–834.  Web of Science CrossRef PubMed CAS
First citationEnraf–Nonius (1994). CAD-4 EXPRESS. Enraf–Nonius, Delft, The Netherlands.
First citationGe, X., Fares, F. A. & Fares, S. Y. (1999). Anticancer Res. 19, 3199–3203.  Web of Science PubMed CAS
First citationHarms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
First citationNi, Y.-C. (2008). Curr. Med. Imaging Rev. 4, 96–112.  Web of Science CrossRef CAS
First citationPoter, J. K., Bacon, C. W., Robins, J. D., Himmelsbach, D. S. & Higman, H. C. (1977). J. Agric. Food Chem. 25, 88–93.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSundberg, R. J. (1996). The Chemistry of Indoles, p. 113. New York: Academic Press.

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