organic compounds
(4S)-3-Methyl-5,6,7,8-tetrahydro-4H-spiro[[1,2]oxazolo[5,4-b]quinoline-4,3′-indole]-2′,5-dione
aDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, bIndustrial Chemistry Laboratory, Central Leather Research Institute, Adyar, Chennai 600 020, India, and cDepartment of Chemistry, D. G. Vaishnav College (Autonomous), Arumbakkam, Chennai 600 106, India
*Correspondence e-mail: a_sp59@yahoo.in
In the title compound, C18H15N3O3, the dihedral angle between the mean planes of the quinoline and indole ring systems [r.m.s. deviations = 0.189 (2) and 0.027 (2) Å, respectively] is 88.65 (5)°. The cyclohexene ring of the quinoline ring system adopts an with the central –CH2– C atom as the flap. In the crystal, molecules are linked by two pairs of N—H⋯O hydrogen bonds, forming inversion dimers, and enclosing R22(14) ring motifs. This arrangement results in the formation of chains propagating along [100].
CCDC reference: 952319
Related literature
For general background to indole, quinoline and pyrrolidine derivatives, see: Padwa et al. (1999). For puckering parameters, see: Cremer & Pople et al. (1975). For asymmetry parameters, see: Nardelli (1983). For hydrogen-bond motifs, see: Bernstein et al. (1995).
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2008); cell SAINT (Bruker, 2008); 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); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).
Supporting information
CCDC reference: 952319
10.1107/S1600536814000130/su2673sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814000130/su2673Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814000130/su2673Isup3.cml
A mixture of isatin (1 mmol), cyclohexane-1,3 dione (1 mmol) and 5-Amino-3-methylisoxazole (1 mmol) in 5 ml of ethanol was heated to 353 K for 6–10 h. The reaction was monitored by TLC. When finished the reaction mixture was filtered hot and the resulting solid products were washed with ethanol, dried in air and recrystallized from ethanol, giving colourless block-like crystals.
N and C-bound H atoms were positioned geometrically and allowed to ride on their parent atoms: N-H = 0.86 Å, C–H = 0.93, 0.97 and 0.96 Å for CH, CH2 and CH3 H atoms, respectively, with Uiso(H) = 1.5Ueq(C-methyl) and = 1.2Ueq(N,C) for other H atoms.
A large number of natural products contain the quinoline and indole heterocycles, and are found in numerous commercial products, including pharmaceuticals, fragrances and dyes (Padwa et al., 1999). In view of the above importance we have synthesized the title compound and report herein on its crystal structure.
The molecular structure of the title molecule is shown in Fig. 1. The quinoline group and indoline ring mean planes [r.m.s = 0.189 (2) and 0.027 (2) Å, respectively] are in axial orientations with a dihedral angle of 88.65 (5)°. The indole ring adopts an almost planar conformation with a maximum deviation 0.0486 (4) Å for the spiro C atom, C10. The quinoline ring system has an φ2 = 209.3 (3)° and the closest pucker descriptor is an envelope on atom C6 of the cyclohexene ring. The sum of the bond angles around atoms N2 and N3 (360 °) of both the quinoline and indole rings indicates sp2 The keto atoms O3 and O2 deviate from the attached ring system of indole and quinoline by -0.032 (1) and -0.021 (1) Å, respectively.
with the puckering parameters (Cremer & Pople, 1975) and the asymmetry parameters (Nardelli,1983) are: q2 = 0.3087 (2) Å,In the crystal, molecules are linked by two pairs of N—H···O hydrogen bonds (Table 1), forming two inversion dimers and containing two R22(14) ring motifs (Bernstein et al., 1995); see Fig. 2. These interactions result in the formation of chains along the a axis direction (Fig. 3 and Table 1).
For general background to indole, quinoline and pyrrolidine derivatives, see: Padwa et al. (1999). For puckering parameters, see: Cremer & Pople et al. (1975). For asymmetry parameters, see: Nardelli (1983). For hydrogen-bond motifs, see: Bernstein et al. (1995).
Data collection: APEX2 (Bruker, 2008); cell
SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).C18H15N3O3 | F(000) = 672 |
Mr = 321.33 | Dx = 1.415 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3088 reflections |
a = 10.9160 (3) Å | θ = 2.0–28.4° |
b = 11.9027 (3) Å | µ = 0.10 mm−1 |
c = 12.4848 (4) Å | T = 293 K |
β = 111.602 (1)° | Block, colourless |
V = 1508.21 (7) Å3 | 0.21 × 0.19 × 0.18 mm |
Z = 4 |
Bruker SMART APEXII CCD diffractometer | 3772 independent reflections |
Radiation source: fine-focus sealed tube | 3088 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
ω and φ scans | θmax = 28.4°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −14→14 |
Tmin = 0.979, Tmax = 0.982 | k = −15→15 |
14019 measured reflections | l = −16→15 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.136 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.067P)2 + 0.5984P] where P = (Fo2 + 2Fc2)/3 |
3772 reflections | (Δ/σ)max < 0.001 |
218 parameters | Δρmax = 0.73 e Å−3 |
0 restraints | Δρmin = −0.35 e Å−3 |
C18H15N3O3 | V = 1508.21 (7) Å3 |
Mr = 321.33 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.9160 (3) Å | µ = 0.10 mm−1 |
b = 11.9027 (3) Å | T = 293 K |
c = 12.4848 (4) Å | 0.21 × 0.19 × 0.18 mm |
β = 111.602 (1)° |
Bruker SMART APEXII CCD diffractometer | 3772 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | 3088 reflections with I > 2σ(I) |
Tmin = 0.979, Tmax = 0.982 | Rint = 0.020 |
14019 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.136 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.73 e Å−3 |
3772 reflections | Δρmin = −0.35 e Å−3 |
218 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.75216 (16) | 1.11349 (13) | 0.22069 (13) | 0.0379 (3) | |
C2 | 0.78149 (13) | 1.02411 (12) | 0.30195 (12) | 0.0305 (3) | |
C3 | 0.90595 (14) | 0.99600 (13) | 0.31647 (13) | 0.0352 (3) | |
C4 | 0.91557 (13) | 0.84446 (12) | 0.43585 (12) | 0.0318 (3) | |
C5 | 0.99809 (15) | 0.74920 (14) | 0.50327 (15) | 0.0404 (3) | |
H5A | 1.0527 | 0.7208 | 0.4631 | 0.048* | |
H5B | 1.0559 | 0.7765 | 0.5780 | 0.048* | |
C6 | 0.9153 (2) | 0.65604 (17) | 0.5196 (2) | 0.0634 (6) | |
H6A | 0.9715 | 0.6024 | 0.5742 | 0.076* | |
H6B | 0.8730 | 0.6175 | 0.4468 | 0.076* | |
C7 | 0.8122 (2) | 0.69692 (18) | 0.5624 (2) | 0.0632 (6) | |
H7A | 0.8541 | 0.7163 | 0.6432 | 0.076* | |
H7B | 0.7508 | 0.6362 | 0.5565 | 0.076* | |
C8 | 0.73613 (14) | 0.79727 (13) | 0.49828 (13) | 0.0356 (3) | |
C9 | 0.78951 (13) | 0.86471 (11) | 0.42928 (12) | 0.0297 (3) | |
C10 | 0.70456 (12) | 0.96318 (11) | 0.36267 (11) | 0.0281 (3) | |
C11 | 0.56686 (13) | 0.93371 (12) | 0.27954 (12) | 0.0309 (3) | |
C12 | 0.52498 (16) | 0.86478 (14) | 0.18423 (13) | 0.0395 (3) | |
H12 | 0.5849 | 0.8222 | 0.1644 | 0.047* | |
C13 | 0.39008 (18) | 0.86039 (15) | 0.11791 (15) | 0.0477 (4) | |
H13 | 0.3598 | 0.8141 | 0.0535 | 0.057* | |
C14 | 0.30162 (17) | 0.92411 (16) | 0.14721 (16) | 0.0501 (4) | |
H14 | 0.2125 | 0.9201 | 0.1017 | 0.060* | |
C15 | 0.34238 (15) | 0.99406 (15) | 0.24296 (15) | 0.0433 (4) | |
H15 | 0.2825 | 1.0366 | 0.2628 | 0.052* | |
C16 | 0.47563 (13) | 0.99759 (12) | 0.30727 (12) | 0.0320 (3) | |
C17 | 0.67211 (13) | 1.04533 (11) | 0.44623 (12) | 0.0294 (3) | |
C18 | 0.62743 (19) | 1.17717 (16) | 0.16867 (16) | 0.0501 (4) | |
H18A | 0.6439 | 1.2452 | 0.1349 | 0.075* | |
H18B | 0.5932 | 1.1953 | 0.2272 | 0.075* | |
H18C | 0.5644 | 1.1322 | 0.1102 | 0.075* | |
N1 | 0.85270 (15) | 1.13783 (13) | 0.19114 (13) | 0.0492 (4) | |
N2 | 0.97711 (12) | 0.91031 (12) | 0.38120 (12) | 0.0402 (3) | |
H2 | 1.0571 | 0.8979 | 0.3876 | 0.048* | |
N3 | 0.54091 (11) | 1.06336 (10) | 0.40459 (10) | 0.0328 (3) | |
H3 | 0.5020 | 1.1098 | 0.4343 | 0.039* | |
O1 | 0.95520 (11) | 1.05973 (11) | 0.25399 (11) | 0.0477 (3) | |
O2 | 0.63136 (11) | 0.82301 (10) | 0.50785 (11) | 0.0443 (3) | |
O3 | 0.75076 (10) | 1.08902 (10) | 0.53253 (9) | 0.0400 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0425 (8) | 0.0408 (8) | 0.0340 (7) | −0.0003 (6) | 0.0181 (6) | 0.0004 (6) |
C2 | 0.0302 (6) | 0.0326 (7) | 0.0325 (7) | −0.0004 (5) | 0.0159 (5) | −0.0017 (5) |
C3 | 0.0315 (7) | 0.0414 (8) | 0.0382 (7) | −0.0035 (6) | 0.0193 (6) | −0.0007 (6) |
C4 | 0.0270 (6) | 0.0347 (7) | 0.0361 (7) | 0.0020 (5) | 0.0144 (5) | −0.0035 (5) |
C5 | 0.0308 (7) | 0.0422 (8) | 0.0499 (8) | 0.0099 (6) | 0.0168 (6) | 0.0033 (7) |
C6 | 0.0460 (10) | 0.0454 (10) | 0.1040 (17) | 0.0139 (8) | 0.0338 (11) | 0.0199 (10) |
C7 | 0.0557 (11) | 0.0594 (12) | 0.0914 (15) | 0.0243 (9) | 0.0471 (11) | 0.0374 (11) |
C8 | 0.0330 (7) | 0.0350 (7) | 0.0446 (8) | 0.0048 (6) | 0.0210 (6) | 0.0029 (6) |
C9 | 0.0262 (6) | 0.0303 (7) | 0.0354 (7) | 0.0025 (5) | 0.0147 (5) | −0.0007 (5) |
C10 | 0.0242 (6) | 0.0308 (7) | 0.0325 (6) | 0.0012 (5) | 0.0142 (5) | −0.0018 (5) |
C11 | 0.0275 (6) | 0.0319 (7) | 0.0344 (7) | 0.0000 (5) | 0.0129 (5) | 0.0006 (5) |
C12 | 0.0408 (8) | 0.0411 (8) | 0.0394 (8) | −0.0027 (6) | 0.0180 (6) | −0.0054 (6) |
C13 | 0.0473 (9) | 0.0492 (10) | 0.0402 (8) | −0.0090 (7) | 0.0084 (7) | −0.0073 (7) |
C14 | 0.0316 (8) | 0.0535 (10) | 0.0532 (10) | −0.0037 (7) | 0.0016 (7) | −0.0006 (8) |
C15 | 0.0274 (7) | 0.0456 (9) | 0.0536 (9) | 0.0042 (6) | 0.0110 (7) | 0.0004 (7) |
C16 | 0.0267 (6) | 0.0332 (7) | 0.0368 (7) | 0.0010 (5) | 0.0124 (5) | 0.0012 (5) |
C17 | 0.0265 (6) | 0.0306 (7) | 0.0341 (7) | 0.0019 (5) | 0.0147 (5) | −0.0004 (5) |
C18 | 0.0540 (10) | 0.0531 (10) | 0.0483 (9) | 0.0138 (8) | 0.0247 (8) | 0.0146 (8) |
N1 | 0.0489 (8) | 0.0562 (9) | 0.0500 (8) | 0.0036 (7) | 0.0271 (7) | 0.0130 (7) |
N2 | 0.0259 (6) | 0.0485 (8) | 0.0521 (8) | 0.0051 (5) | 0.0212 (6) | 0.0070 (6) |
N3 | 0.0265 (6) | 0.0345 (6) | 0.0402 (6) | 0.0047 (4) | 0.0155 (5) | −0.0044 (5) |
O1 | 0.0399 (6) | 0.0584 (7) | 0.0549 (7) | 0.0002 (5) | 0.0293 (5) | 0.0115 (6) |
O2 | 0.0385 (6) | 0.0459 (6) | 0.0609 (7) | 0.0082 (5) | 0.0328 (6) | 0.0084 (5) |
O3 | 0.0289 (5) | 0.0498 (6) | 0.0411 (6) | −0.0005 (4) | 0.0125 (4) | −0.0127 (5) |
C1—N1 | 1.312 (2) | C10—C11 | 1.5201 (18) |
C1—C2 | 1.423 (2) | C10—C17 | 1.5628 (18) |
C1—C18 | 1.483 (2) | C11—C12 | 1.377 (2) |
C2—C3 | 1.3451 (19) | C11—C16 | 1.3941 (19) |
C2—C10 | 1.5082 (18) | C12—C13 | 1.400 (2) |
C3—O1 | 1.3348 (17) | C12—H12 | 0.9300 |
C3—N2 | 1.355 (2) | C13—C14 | 1.379 (3) |
C4—N2 | 1.3668 (19) | C13—H13 | 0.9300 |
C4—C9 | 1.3695 (18) | C14—C15 | 1.389 (3) |
C4—C5 | 1.499 (2) | C14—H14 | 0.9300 |
C5—C6 | 1.491 (3) | C15—C16 | 1.379 (2) |
C5—H5A | 0.9700 | C15—H15 | 0.9300 |
C5—H5B | 0.9700 | C16—N3 | 1.3998 (19) |
C6—C7 | 1.494 (3) | C17—O3 | 1.2195 (17) |
C6—H6A | 0.9700 | C17—N3 | 1.3487 (17) |
C6—H6B | 0.9700 | C18—H18A | 0.9600 |
C7—C8 | 1.506 (2) | C18—H18B | 0.9600 |
C7—H7A | 0.9700 | C18—H18C | 0.9600 |
C7—H7B | 0.9700 | N1—O1 | 1.4440 (19) |
C8—O2 | 1.2315 (17) | N2—H2 | 0.8600 |
C8—C9 | 1.448 (2) | N3—H3 | 0.8600 |
C9—C10 | 1.5354 (19) | ||
N1—C1—C2 | 111.93 (14) | C2—C10—C17 | 109.86 (11) |
N1—C1—C18 | 119.47 (14) | C11—C10—C17 | 100.95 (10) |
C2—C1—C18 | 128.59 (14) | C9—C10—C17 | 110.86 (11) |
C3—C2—C1 | 103.48 (13) | C12—C11—C16 | 119.94 (13) |
C3—C2—C10 | 122.29 (13) | C12—C11—C10 | 131.11 (13) |
C1—C2—C10 | 134.21 (13) | C16—C11—C10 | 108.77 (12) |
O1—C3—C2 | 112.58 (14) | C11—C12—C13 | 118.39 (15) |
O1—C3—N2 | 120.71 (13) | C11—C12—H12 | 120.8 |
C2—C3—N2 | 126.63 (13) | C13—C12—H12 | 120.8 |
N2—C4—C9 | 122.47 (13) | C14—C13—C12 | 120.63 (16) |
N2—C4—C5 | 114.19 (12) | C14—C13—H13 | 119.7 |
C9—C4—C5 | 123.34 (13) | C12—C13—H13 | 119.7 |
C6—C5—C4 | 111.73 (13) | C13—C14—C15 | 121.62 (15) |
C6—C5—H5A | 109.3 | C13—C14—H14 | 119.2 |
C4—C5—H5A | 109.3 | C15—C14—H14 | 119.2 |
C6—C5—H5B | 109.3 | C16—C15—C14 | 117.02 (15) |
C4—C5—H5B | 109.3 | C16—C15—H15 | 121.5 |
H5A—C5—H5B | 107.9 | C14—C15—H15 | 121.5 |
C5—C6—C7 | 112.39 (17) | C15—C16—C11 | 122.38 (14) |
C5—C6—H6A | 109.1 | C15—C16—N3 | 127.81 (13) |
C7—C6—H6A | 109.1 | C11—C16—N3 | 109.79 (12) |
C5—C6—H6B | 109.1 | O3—C17—N3 | 125.10 (13) |
C7—C6—H6B | 109.1 | O3—C17—C10 | 126.70 (12) |
H6A—C6—H6B | 107.9 | N3—C17—C10 | 108.16 (11) |
C6—C7—C8 | 114.14 (16) | C1—C18—H18A | 109.5 |
C6—C7—H7A | 108.7 | C1—C18—H18B | 109.5 |
C8—C7—H7A | 108.7 | H18A—C18—H18B | 109.5 |
C6—C7—H7B | 108.7 | C1—C18—H18C | 109.5 |
C8—C7—H7B | 108.7 | H18A—C18—H18C | 109.5 |
H7A—C7—H7B | 107.6 | H18B—C18—H18C | 109.5 |
O2—C8—C9 | 120.75 (13) | C1—N1—O1 | 105.43 (12) |
O2—C8—C7 | 119.74 (14) | C3—N2—C4 | 116.76 (12) |
C9—C8—C7 | 119.47 (13) | C3—N2—H2 | 121.6 |
C4—C9—C8 | 118.85 (13) | C4—N2—H2 | 121.6 |
C4—C9—C10 | 124.05 (12) | C17—N3—C16 | 112.00 (11) |
C8—C9—C10 | 116.77 (11) | C17—N3—H3 | 124.0 |
C2—C10—C11 | 111.19 (11) | C16—N3—H3 | 124.0 |
C2—C10—C9 | 107.60 (10) | C3—O1—N1 | 106.57 (11) |
C11—C10—C9 | 116.23 (11) | ||
N1—C1—C2—C3 | −1.17 (18) | C9—C10—C11—C12 | −60.3 (2) |
C18—C1—C2—C3 | 178.32 (17) | C17—C10—C11—C12 | 179.74 (15) |
N1—C1—C2—C10 | −179.41 (15) | C2—C10—C11—C16 | −111.75 (13) |
C18—C1—C2—C10 | 0.1 (3) | C9—C10—C11—C16 | 124.72 (13) |
C1—C2—C3—O1 | 0.85 (17) | C17—C10—C11—C16 | 4.74 (14) |
C10—C2—C3—O1 | 179.36 (12) | C16—C11—C12—C13 | −0.5 (2) |
C1—C2—C3—N2 | −176.02 (15) | C10—C11—C12—C13 | −175.05 (15) |
C10—C2—C3—N2 | 2.5 (2) | C11—C12—C13—C14 | 0.3 (3) |
N2—C4—C5—C6 | −156.45 (16) | C12—C13—C14—C15 | −0.3 (3) |
C9—C4—C5—C6 | 23.7 (2) | C13—C14—C15—C16 | 0.4 (3) |
C4—C5—C6—C7 | −49.1 (2) | C14—C15—C16—C11 | −0.6 (2) |
C5—C6—C7—C8 | 47.0 (3) | C14—C15—C16—N3 | 177.92 (15) |
C6—C7—C8—O2 | 164.00 (19) | C12—C11—C16—C15 | 0.7 (2) |
C6—C7—C8—C9 | −18.2 (3) | C10—C11—C16—C15 | 176.31 (14) |
N2—C4—C9—C8 | −174.34 (13) | C12—C11—C16—N3 | −178.08 (13) |
C5—C4—C9—C8 | 5.5 (2) | C10—C11—C16—N3 | −2.43 (16) |
N2—C4—C9—C10 | −1.1 (2) | C2—C10—C17—O3 | −66.12 (18) |
C5—C4—C9—C10 | 178.73 (13) | C11—C10—C17—O3 | 176.41 (14) |
O2—C8—C9—C4 | 169.38 (15) | C9—C10—C17—O3 | 52.67 (19) |
C7—C8—C9—C4 | −8.4 (2) | C2—C10—C17—N3 | 111.85 (13) |
O2—C8—C9—C10 | −4.4 (2) | C11—C10—C17—N3 | −5.62 (14) |
C7—C8—C9—C10 | 177.81 (16) | C9—C10—C17—N3 | −129.36 (12) |
C3—C2—C10—C11 | −132.98 (14) | C2—C1—N1—O1 | 1.00 (18) |
C1—C2—C10—C11 | 45.0 (2) | C18—C1—N1—O1 | −178.54 (15) |
C3—C2—C10—C9 | −4.65 (18) | O1—C3—N2—C4 | −175.45 (13) |
C1—C2—C10—C9 | 173.33 (15) | C2—C3—N2—C4 | 1.2 (2) |
C3—C2—C10—C17 | 116.13 (15) | C9—C4—N2—C3 | −1.9 (2) |
C1—C2—C10—C17 | −65.9 (2) | C5—C4—N2—C3 | 178.32 (14) |
C4—C9—C10—C2 | 4.05 (18) | O3—C17—N3—C16 | −177.34 (14) |
C8—C9—C10—C2 | 177.46 (12) | C10—C17—N3—C16 | 4.65 (16) |
C4—C9—C10—C11 | 129.43 (14) | C15—C16—N3—C17 | 179.84 (15) |
C8—C9—C10—C11 | −57.17 (16) | C11—C16—N3—C17 | −1.51 (17) |
C4—C9—C10—C17 | −116.09 (15) | C2—C3—O1—N1 | −0.29 (17) |
C8—C9—C10—C17 | 57.31 (16) | N2—C3—O1—N1 | 176.78 (14) |
C2—C10—C11—C12 | 63.2 (2) | C1—N1—O1—C3 | −0.45 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O3i | 0.86 | 1.97 | 2.7620 (16) | 153 |
N3—H3···O2ii | 0.86 | 2.01 | 2.8415 (16) | 161 |
Symmetry codes: (i) −x+2, −y+2, −z+1; (ii) −x+1, −y+2, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O3i | 0.86 | 1.97 | 2.7620 (16) | 153 |
N3—H3···O2ii | 0.86 | 2.01 | 2.8415 (16) | 161 |
Symmetry codes: (i) −x+2, −y+2, −z+1; (ii) −x+1, −y+2, −z+1. |
Acknowledgements
The authors thank the TBI X-ray facility, CAS in Crystallography and BioPhysics, University of Madras, Chennai, India, for the data collection.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
A large number of natural products contain the quinoline and indole heterocycles, and are found in numerous commercial products, including pharmaceuticals, fragrances and dyes (Padwa et al., 1999). In view of the above importance we have synthesized the title compound and report herein on its crystal structure.
The molecular structure of the title molecule is shown in Fig. 1. The quinoline group and indoline ring mean planes [r.m.s = 0.189 (2) and 0.027 (2) Å, respectively] are in axial orientations with a dihedral angle of 88.65 (5)°. The indole ring adopts an almost planar conformation with a maximum deviation 0.0486 (4) Å for the spiro C atom, C10. The quinoline ring system has an envelope conformation with the puckering parameters (Cremer & Pople, 1975) and the asymmetry parameters (Nardelli,1983) are: q2 = 0.3087 (2) Å, φ2 = 209.3 (3)° and the closest pucker descriptor is an envelope on atom C6 of the cyclohexene ring. The sum of the bond angles around atoms N2 and N3 (360 °) of both the quinoline and indole rings indicates sp2 hybridization. The keto atoms O3 and O2 deviate from the attached ring system of indole and quinoline by -0.032 (1) and -0.021 (1) Å, respectively.
In the crystal, molecules are linked by two pairs of N—H···O hydrogen bonds (Table 1), forming two inversion dimers and containing two R22(14) ring motifs (Bernstein et al., 1995); see Fig. 2. These interactions result in the formation of chains along the a axis direction (Fig. 3 and Table 1).