Literature DB >> 23795093

3,4-Bis[1-(prop-2-yn-yl)-1H-indol-3-yl]-1H-pyrrole-2,5-dione.

Mu-Hua Huang1, Yong-Chen Gao, Feng-Ling Yang, Yun-Jun Luo.   

Abstract

In the title mol-ecule, C26H17N3O2, both indole ring systems are essentially planar, with maximum deviations of 0.019 (2) and 0.033 (1) Å for the N atoms, and form dihedral angles of 34.40 (9) and 45.06 (8)° with the essentially planar pyrrole ring [maximum deviation = 0.020 (2) Å]. The dihedral angle between the two indole ring systems is 58.78 (6)°. In the crystal, mol-ecules are connected by pairs of N-H⋯O hydrogen bonds, forming inversion dimers and generating R 2 (2)(8) rings. Weak π-π stacking inter-actions, with a centroid-centroid distance of 3.983 (2) Å, are also observed.

Entities:  

Year:  2013        PMID： 23795093      PMCID： PMC3685074          DOI： 10.1107/S1600536813012889

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For the importance of bis­indolylmale­imides in medicinal chemistry, see: Bulbule et al. (2008 ▶); Wang et al. (2012 ▶) and in materials science, see: Chiu et al. (2003 ▶); Kaletas et al. (2005 ▶); Lin et al. (2010 ▶); Nakazono et al. (2007 ▶); Yeh et al. (2006 ▶). For the isolation of bis­indolylmale­imides from natural products, see: Kamata et al. (2006 ▶). For the synthesis of bis­indol­yl­mal­e­­i­mides, see: Prateeptongkum et al. (2010 ▶). For a related crystal structure, see: Huang et al. (2012 ▶). For hydrogen-bond graph-set motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C26H17N3O2 M = 403.43 Triclinic, a = 8.8015 (14) Å b = 11.2619 (14) Å c = 11.838 (3) Å α = 62.860 (17)° β = 73.625 (16)° γ = 79.593 (12)° V = 999.9 (3) Å3 Z = 2 Mo Kα radiation μ = 0.09 mm−1 T = 102 K 0.11 × 0.10 × 0.07 mm

Data collection

Bruker SMART CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.991, T max = 0.994 6379 measured reflections 3920 independent reflections 3113 reflections with I > 2σ(I) R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.049 wR(F 2) = 0.114 S = 1.03 3920 reflections 280 parameters H-atom parameters constrained Δρmax = 0.37 e Å−3 Δρmin = −0.23 e Å−3 Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶). Click here for additional data file. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813012889/lh5613sup1.cif Click here for additional data file. Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813012889/lh5613Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536813012889/lh5613Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C26H17N3O2V = 999.9 (3) Å3
Mr = 403.43Z = 2
Triclinic, P1F(000) = 420
Hall symbol: -P 1Dx = 1.340 Mg m−3
a = 8.8015 (14) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.2619 (14) Åθ = 1.5–51.8°
c = 11.838 (3) ŵ = 0.09 mm−1
α = 62.860 (17)°T = 102 K
β = 73.625 (16)°Block, colorless
γ = 79.593 (12)°0.11 × 0.10 × 0.07 mm
Bruker SMART CCD diffractometer3920 independent reflections
Radiation source: fine-focus sealed tube3113 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
φ and ω scansθmax = 26.0°, θmin = 3.3°
Absorption correction: multi-scan (SADABS; Bruker, 2002)h = −10→9
Tmin = 0.991, Tmax = 0.994k = −13→13
6379 measured reflectionsl = −11→14
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0438P)2 + 0.3377P] where P = (Fo2 + 2Fc2)/3
3920 reflections(Δ/σ)max < 0.001
280 parametersΔρmax = 0.37 e Å−3
0 restraintsΔρmin = −0.23 e Å−3
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.
xyzUiso*/Ueq
O20.33248 (15)0.75325 (12)0.29355 (12)0.0242 (3)
O10.11940 (15)0.34749 (12)0.48806 (13)0.0248 (3)
C120.7380 (2)0.27334 (17)0.39074 (16)0.0203 (4)
H120.72780.35310.40170.024*
C200.8983 (2)0.62081 (19)−0.09736 (18)0.0259 (4)
H200.97900.6819−0.15020.031*
C190.7956 (2)0.62914 (17)0.01340 (17)0.0200 (4)
N20.48798 (18)0.09433 (14)0.33954 (14)0.0202 (3)
C180.6728 (2)0.54223 (17)0.09277 (17)0.0185 (4)
C230.6555 (2)0.44154 (18)0.05835 (18)0.0239 (4)
H230.57410.38070.10930.029*
N30.79109 (19)0.71857 (15)0.06452 (15)0.0253 (4)
C170.5904 (2)0.58517 (17)0.19368 (17)0.0205 (4)
C70.6120 (2)0.23464 (17)0.36673 (16)0.0180 (4)
C90.7717 (2)0.03492 (18)0.35768 (18)0.0245 (4)
H90.7834−0.04430.34560.029*
C140.5187 (2)0.04567 (18)0.15627 (19)0.0250 (4)
C160.6670 (2)0.69296 (18)0.17015 (19)0.0260 (4)
H160.63750.74270.22060.031*
C130.4647 (2)−0.00393 (18)0.29867 (18)0.0247 (4)
H13A0.3508−0.02180.32550.030*
H13B0.5249−0.08890.34180.030*
C80.6308 (2)0.11411 (17)0.35377 (16)0.0194 (4)
C40.3246 (2)0.63429 (17)0.32913 (17)0.0201 (4)
C220.7586 (2)0.4323 (2)−0.05068 (19)0.0287 (5)
H220.74750.3643−0.07370.034*
C110.8770 (2)0.19342 (19)0.39814 (17)0.0250 (4)
H110.96240.21790.41580.030*
C50.3823 (2)0.19972 (17)0.34038 (17)0.0201 (4)
H50.27630.20980.33120.024*
N10.19290 (18)0.56262 (14)0.41135 (15)0.0228 (4)
H10.10590.59570.44840.027*
C100.8942 (2)0.07670 (19)0.37999 (18)0.0271 (4)
H100.99230.02510.38310.033*
C20.3827 (2)0.41642 (17)0.35429 (17)0.0178 (4)
C150.5634 (3)0.09309 (19)0.0417 (2)0.0320 (5)
H150.59930.1313−0.05050.038*
C60.4527 (2)0.28858 (17)0.35655 (16)0.0181 (4)
C30.4463 (2)0.53771 (17)0.29249 (17)0.0189 (4)
C210.8777 (2)0.5207 (2)−0.12664 (18)0.0291 (5)
H210.94660.5118−0.20060.035*
C250.9581 (2)0.83373 (18)0.1088 (2)0.0277 (5)
C10.2178 (2)0.43211 (17)0.42665 (17)0.0198 (4)
C240.8937 (3)0.8296 (2)0.0096 (2)0.0328 (5)
H24A0.83220.9148−0.03060.039*
H24B0.98220.8204−0.05980.039*
C261.0093 (3)0.83789 (19)0.1887 (2)0.0344 (5)
H261.05060.84130.25310.041*
U11U22U33U12U13U23
O20.0229 (8)0.0190 (7)0.0286 (7)−0.0038 (5)−0.0003 (6)−0.0108 (6)
O10.0188 (7)0.0217 (7)0.0301 (7)−0.0056 (5)0.0049 (6)−0.0124 (6)
C120.0228 (10)0.0222 (9)0.0144 (8)−0.0046 (7)−0.0031 (7)−0.0062 (8)
C200.0177 (10)0.0301 (11)0.0183 (9)−0.0005 (8)−0.0007 (8)−0.0027 (9)
C190.0159 (10)0.0201 (9)0.0194 (9)0.0026 (7)−0.0061 (7)−0.0046 (8)
N20.0214 (9)0.0190 (8)0.0198 (8)−0.0028 (6)−0.0025 (6)−0.0088 (7)
C180.0136 (9)0.0201 (9)0.0162 (9)0.0001 (7)−0.0044 (7)−0.0029 (8)
C230.0204 (10)0.0291 (10)0.0203 (9)−0.0001 (8)−0.0058 (8)−0.0088 (8)
N30.0210 (9)0.0246 (9)0.0238 (8)−0.0074 (6)0.0013 (7)−0.0065 (7)
C170.0157 (10)0.0184 (9)0.0221 (9)−0.0007 (7)−0.0010 (7)−0.0064 (8)
C70.0184 (10)0.0197 (9)0.0114 (8)−0.0020 (7)−0.0003 (7)−0.0043 (7)
C90.0269 (11)0.0213 (10)0.0193 (9)0.0018 (8)−0.0027 (8)−0.0063 (8)
C140.0304 (11)0.0198 (10)0.0279 (11)−0.0038 (8)−0.0065 (9)−0.0120 (9)
C160.0244 (11)0.0236 (10)0.0263 (10)−0.0048 (8)0.0023 (8)−0.0110 (9)
C130.0310 (12)0.0204 (10)0.0247 (10)−0.0053 (8)−0.0044 (9)−0.0110 (8)
C80.0213 (10)0.0196 (9)0.0138 (8)−0.0031 (7)−0.0021 (7)−0.0045 (7)
C40.0183 (10)0.0212 (10)0.0195 (9)−0.0049 (7)−0.0012 (7)−0.0082 (8)
C220.0279 (12)0.0329 (11)0.0241 (10)0.0027 (8)−0.0087 (9)−0.0112 (9)
C110.0198 (10)0.0327 (11)0.0170 (9)−0.0050 (8)−0.0048 (8)−0.0043 (8)
C50.0166 (10)0.0211 (9)0.0187 (9)−0.0035 (7)0.0005 (7)−0.0070 (8)
N10.0174 (8)0.0203 (8)0.0274 (8)−0.0028 (6)0.0058 (7)−0.0133 (7)
C100.0211 (11)0.0293 (11)0.0211 (10)0.0048 (8)−0.0042 (8)−0.0052 (9)
C20.0149 (9)0.0219 (9)0.0171 (9)−0.0024 (7)−0.0017 (7)−0.0093 (8)
C150.0466 (14)0.0262 (11)0.0252 (11)−0.0083 (9)−0.0066 (10)−0.0114 (9)
C60.0178 (10)0.0188 (9)0.0147 (8)−0.0031 (7)0.0013 (7)−0.0069 (7)
C30.0172 (10)0.0205 (9)0.0185 (9)−0.0009 (7)−0.0015 (7)−0.0094 (8)
C210.0249 (11)0.0393 (12)0.0197 (10)0.0076 (9)−0.0048 (8)−0.0135 (9)
C250.0206 (11)0.0220 (10)0.0340 (11)−0.0060 (8)0.0004 (9)−0.0088 (9)
C10.0190 (10)0.0199 (9)0.0201 (9)−0.0036 (7)−0.0004 (8)−0.0099 (8)
C240.0291 (12)0.0299 (11)0.0305 (11)−0.0137 (9)0.0008 (9)−0.0055 (9)
C260.0323 (13)0.0262 (11)0.0406 (13)−0.0017 (9)−0.0068 (10)−0.0118 (10)
O2—C41.216 (2)C14—C151.180 (3)
O1—C11.224 (2)C14—C131.471 (3)
C12—C111.380 (3)C16—H160.9500
C12—C71.402 (2)C13—H13A0.9900
C12—H120.9500C13—H13B0.9900
C20—C211.375 (3)C4—N11.388 (2)
C20—C191.399 (3)C4—C31.506 (2)
C20—H200.9500C22—C211.388 (3)
C19—N31.382 (2)C22—H220.9500
C19—C181.407 (2)C11—C101.402 (3)
N2—C51.371 (2)C11—H110.9500
N2—C81.383 (2)C5—C61.374 (2)
N2—C131.459 (2)C5—H50.9500
C18—C231.412 (3)N1—C11.380 (2)
C18—C171.449 (3)N1—H10.8800
C23—C221.389 (3)C10—H100.9500
C23—H230.9500C2—C31.359 (2)
N3—C161.362 (2)C2—C61.451 (2)
N3—C241.462 (2)C2—C11.489 (2)
C17—C161.374 (2)C15—H150.9500
C17—C31.449 (2)C21—H210.9500
C7—C81.410 (2)C25—C261.178 (3)
C7—C61.439 (2)C25—C241.463 (3)
C9—C101.382 (3)C24—H24A0.9900
C9—C81.390 (3)C24—H24B0.9900
C9—H90.9500C26—H260.9500
C11—C12—C7118.76 (17)O2—C4—N1124.49 (17)
C11—C12—H12120.6O2—C4—C3128.73 (16)
C7—C12—H12120.6N1—C4—C3106.75 (14)
C21—C20—C19117.34 (18)C21—C22—C23121.13 (19)
C21—C20—H20121.3C21—C22—H22119.4
C19—C20—H20121.3C23—C22—H22119.4
N3—C19—C20129.06 (17)C12—C11—C10121.12 (18)
N3—C19—C18107.88 (16)C12—C11—H11119.4
C20—C19—C18123.06 (17)C10—C11—H11119.4
C5—N2—C8109.07 (14)N2—C5—C6109.78 (16)
C5—N2—C13124.26 (16)N2—C5—H5125.1
C8—N2—C13125.14 (15)C6—C5—H5125.1
C19—C18—C23117.57 (16)C1—N1—C4110.35 (15)
C19—C18—C17106.66 (15)C1—N1—H1124.8
C23—C18—C17135.75 (17)C4—N1—H1124.8
C22—C23—C18119.34 (18)C9—C10—C11121.56 (18)
C22—C23—H23120.3C9—C10—H10119.2
C18—C23—H23120.3C11—C10—H10119.2
C16—N3—C19108.84 (15)C3—C2—C6129.71 (17)
C16—N3—C24124.81 (16)C3—C2—C1108.11 (15)
C19—N3—C24126.19 (16)C6—C2—C1122.18 (15)
C16—C17—C18106.03 (16)C14—C15—H15180.0
C16—C17—C3124.76 (17)C5—C6—C7106.70 (15)
C18—C17—C3128.89 (16)C5—C6—C2126.26 (17)
C12—C7—C8118.80 (17)C7—C6—C2126.90 (15)
C12—C7—C6134.27 (16)C2—C3—C17131.66 (16)
C8—C7—C6106.86 (15)C2—C3—C4107.35 (15)
C10—C9—C8116.94 (17)C17—C3—C4120.44 (15)
C10—C9—H9121.5C20—C21—C22121.54 (19)
C8—C9—H9121.5C20—C21—H21119.2
C15—C14—C13175.8 (2)C22—C21—H21119.2
N3—C16—C17110.56 (17)C26—C25—C24179.5 (2)
N3—C16—H16124.7O1—C1—N1125.03 (17)
C17—C16—H16124.7O1—C1—C2127.66 (16)
N2—C13—C14110.29 (15)N1—C1—C2107.30 (14)
N2—C13—H13A109.6N3—C24—C25111.76 (16)
C14—C13—H13A109.6N3—C24—H24A109.3
N2—C13—H13B109.6C25—C24—H24A109.3
C14—C13—H13B109.6N3—C24—H24B109.3
H13A—C13—H13B108.1C25—C24—H24B109.3
N2—C8—C9129.68 (17)H24A—C24—H24B107.9
N2—C8—C7107.57 (16)C25—C26—H26180.0
C9—C8—C7122.74 (17)
C21—C20—C19—N3179.63 (18)C13—N2—C5—C6−167.15 (15)
C21—C20—C19—C18−1.3 (3)O2—C4—N1—C1176.33 (18)
N3—C19—C18—C23−179.89 (15)C3—C4—N1—C1−1.9 (2)
C20—C19—C18—C230.8 (3)C8—C9—C10—C110.1 (3)
N3—C19—C18—C171.25 (19)C12—C11—C10—C9−1.8 (3)
C20—C19—C18—C17−178.03 (16)N2—C5—C6—C7−0.17 (19)
C19—C18—C23—C220.0 (3)N2—C5—C6—C2175.86 (16)
C17—C18—C23—C22178.43 (19)C12—C7—C6—C5−175.92 (18)
C20—C19—N3—C16177.35 (18)C8—C7—C6—C50.94 (19)
C18—C19—N3—C16−1.9 (2)C12—C7—C6—C28.1 (3)
C20—C19—N3—C241.8 (3)C8—C7—C6—C2−175.05 (16)
C18—C19—N3—C24−177.39 (17)C3—C2—C6—C5−134.3 (2)
C19—C18—C17—C16−0.2 (2)C1—C2—C6—C546.1 (3)
C23—C18—C17—C16−178.7 (2)C3—C2—C6—C740.9 (3)
C19—C18—C17—C3173.55 (18)C1—C2—C6—C7−138.68 (18)
C23—C18—C17—C3−5.0 (3)C6—C2—C3—C1711.6 (3)
C11—C12—C7—C81.3 (2)C1—C2—C3—C17−168.76 (19)
C11—C12—C7—C6177.89 (18)C6—C2—C3—C4−177.07 (17)
C19—N3—C16—C171.8 (2)C1—C2—C3—C42.5 (2)
C24—N3—C16—C17177.39 (17)C16—C17—C3—C2−157.5 (2)
C18—C17—C16—N3−1.0 (2)C18—C17—C3—C229.8 (3)
C3—C17—C16—N3−175.05 (17)C16—C17—C3—C432.1 (3)
C5—N2—C13—C1484.9 (2)C18—C17—C3—C4−140.54 (18)
C8—N2—C13—C14−79.4 (2)O2—C4—C3—C2−178.66 (18)
C5—N2—C8—C9−179.60 (18)N1—C4—C3—C2−0.5 (2)
C13—N2—C8—C9−13.3 (3)O2—C4—C3—C17−6.2 (3)
C5—N2—C8—C71.29 (19)N1—C4—C3—C17171.94 (16)
C13—N2—C8—C7167.59 (15)C19—C20—C21—C220.9 (3)
C10—C9—C8—N2−176.65 (17)C23—C22—C21—C20−0.1 (3)
C10—C9—C8—C72.4 (3)C4—N1—C1—O1−175.96 (18)
C12—C7—C8—N2176.07 (15)C4—N1—C1—C23.4 (2)
C6—C7—C8—N2−1.36 (19)C3—C2—C1—O1175.62 (18)
C12—C7—C8—C9−3.1 (3)C6—C2—C1—O1−4.7 (3)
C6—C7—C8—C9179.45 (16)C3—C2—C1—N1−3.8 (2)
C18—C23—C22—C21−0.3 (3)C6—C2—C1—N1175.90 (16)
C7—C12—C11—C101.1 (3)C16—N3—C24—C2552.3 (3)
C8—N2—C5—C6−0.7 (2)C19—N3—C24—C25−132.89 (19)
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.882.012.872 (2)165
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
N1—H1⋯O1i 0.882.012.872 (2)165

Symmetry code: (i) .

  7 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  Efficient synthesis of biologically interesting 3,4-diaryl-substituted succinimides and maleimides: application of iron-catalyzed carbonylations.

Authors:  Saisuree Prateeptongkum; Katrin Marie Driller; Ralf Jackstell; Anke Spannenberg; Matthias Beller
Journal:  Chemistry       Date:  2010-08-16       Impact factor: 5.236

3.  Bisindole alkaloids from myxomycetes Arcyria denudata and Arcyria obvelata.

Authors:  Kazuaki Kamata; Tomoko Suetsugu; Yukinori Yamamoto; Masahiko Hayashi; Kanki Komiyama; Masami Ishibashi
Journal:  J Nat Prod       Date:  2006-08       Impact factor: 4.050

4.  2-Oxotetrahydroquinoline-based antimalarials with high potency and metabolic stability.

Authors:  Vivek J Bulbule; Kasey Rivas; Christophe L M J Verlinde; Wesley C Van Voorhis; Michael H Gelb
Journal:  J Med Chem       Date:  2008-01-17       Impact factor: 7.446

5.  Bisindolylmaleimides with large Stokes shift and long-lasting chemiluminescence properties.

Authors:  Manabu Nakazono; Shinkoh Nanbu; Akihiro Uesaki; Ryoichi Kuwano; Manabu Kashiwabara; Kiyoshi Zaitsu
Journal:  Org Lett       Date:  2007-08-08       Impact factor: 6.005

6.  3,4-Bis(4-meth-oxy-phen-yl)-2,5-dihydro-1H-pyrrole-2,5-dione.

Authors:  Liangzhu Huang; Youqiang Li; Dongmei Gao; Zhenting Du
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-04-06

7.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
  7 in total
  1 in total

1.  PKC signal amplification suppresses non-small cell lung cancer growth by promoting p21 expression and phosphorylation.

Authors:  Shuyan Liu; Yayun Zhang; Qianyi Yang; Yingqiu Zhang; Han Liu; Mu-Hua Huang; Ruoyu Wang; Faqiang Lu
Journal:  Heliyon       Date:  2022-09-17
  1 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.