organic compounds
(4S)-5′-Chloro-3,7,7-trimethyl-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 cD. G. Vaishnav College (Autonomous), Arumbakkam, Chennai 600 106, India
*Correspondence e-mail: a_sp59@yahoo.in
In the title compound, C20H18ClN3O3, the five- and six-membered heterocycles fused through a spiro C atom are inclined to each other at an angle of 87.4 (1)°. In the tricyclic ring system, the cyclohexene ring adopts an with the as the flap. In the crystal, two sets of N—H⋯O hydrogen bonds link the molecules into columns containing centrosymmetric R22(7) ring motifs and propagating along the b-axis direction.
CCDC reference: 952320
Related literature
For applications of indole, quinoline and pyrrolidine derivatives, see: Padwa et al. (1999). 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: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).
Supporting information
CCDC reference: 952320
10.1107/S1600536814000191/cv5438sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814000191/cv5438Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814000191/cv5438Isup3.cml
A reaction mixture of 5-chloro isatin (1 mmol), 5,5-dimethylcyclohexane-1,3 dione (1 mmol) and 5-amino-3-methylisoxazole (1 mmol) in 5 ml of ethanol was heated up to 80°C for 6–10 h. The reaction was monitored by TLC. Then, the reaction mixture was filtered hot and the resulting solid products were washed with ethanol, dried in an air and recrystallized from ethanol.
All H atoms were positioned geometrically (C–H = 0.93–0.98 Å, N–H = 0.86 Å) and allowed to ride on their parent atoms, with Uiso(H) = 1.2–1.5Ueq(C, N).
A large number of natural products contain the quinoline and indole heterocycles, and they are found in numerous commercial products, including pharmaceuticals, fragrances and dyes (Padwa et al., 1999). In view of the above importance, crystallographic study of the title compound (I) has been carried out to establish its molecular structure.
In (I) (Fig. 1), the indole ring adopts slightly
on atom C7. The sum of the bond angle around atom N3 (360°) of the quinoline ring indicates sp2 The quinoline group and indole ring are in axial orientation with the dihedral angle between them as 87.39 (1)°. The indole and quinoline ring systems are planar and keto atoms O1 and O3 deviate from the attached ring system by -0.024 (1) and -0.012 (2) Å, respectively.In the crystal, molecules are linked by two sets of N—H···O hydrogen bonds (Table 1), forming centrosymmetric dimers containing two R22(7) ring motifs (Bernstein et al., 1995).
For applications of indole, quinoline and pyrrolidine derivatives, see: Padwa et al. (1999). 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: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).Fig. 1. The molecular structure of the title compound, showing the atomic numbering and displacement ellipsoids drawn at 30% probability level. |
C20H18ClN3O3 | F(000) = 1600 |
Mr = 383.82 | Dx = 1.376 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 2643 reflections |
a = 17.9320 (7) Å | θ = 2.2–28.3° |
b = 11.1120 (4) Å | µ = 0.23 mm−1 |
c = 18.5968 (7) Å | T = 293 K |
V = 3705.6 (2) Å3 | Block, white |
Z = 8 | 0.21 × 0.19 × 0.18 mm |
Bruker SMART APEXII CCD diffractometer | 4590 independent reflections |
Radiation source: fine-focus sealed tube | 2643 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
ω and φ scans | θmax = 28.3°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −22→23 |
Tmin = 0.952, Tmax = 0.959 | k = −14→12 |
17841 measured reflections | l = −24→24 |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.134 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0522P)2 + 1.5319P] where P = (Fo2 + 2Fc2)/3 |
4590 reflections | (Δ/σ)max < 0.001 |
247 parameters | Δρmax = 0.29 e Å−3 |
0 restraints | Δρmin = −0.36 e Å−3 |
C20H18ClN3O3 | V = 3705.6 (2) Å3 |
Mr = 383.82 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 17.9320 (7) Å | µ = 0.23 mm−1 |
b = 11.1120 (4) Å | T = 293 K |
c = 18.5968 (7) Å | 0.21 × 0.19 × 0.18 mm |
Bruker SMART APEXII CCD diffractometer | 4590 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | 2643 reflections with I > 2σ(I) |
Tmin = 0.952, Tmax = 0.959 | Rint = 0.032 |
17841 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.134 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.29 e Å−3 |
4590 reflections | Δρmin = −0.36 e Å−3 |
247 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 | ||
C3 | 0.72085 (13) | 0.4404 (3) | 0.61785 (14) | 0.0621 (7) | |
C4 | 0.70766 (15) | 0.5417 (3) | 0.57753 (16) | 0.0718 (8) | |
H4 | 0.7341 | 0.6117 | 0.5874 | 0.086* | |
C5 | 0.65605 (15) | 0.5416 (2) | 0.52285 (14) | 0.0611 (7) | |
H5 | 0.6470 | 0.6104 | 0.4957 | 0.073* | |
C6 | 0.61833 (12) | 0.43645 (18) | 0.50978 (11) | 0.0441 (5) | |
C7 | 0.53305 (12) | 0.30227 (16) | 0.46674 (10) | 0.0372 (5) | |
C8 | 0.58105 (11) | 0.23360 (16) | 0.52297 (9) | 0.0339 (4) | |
C1 | 0.63164 (11) | 0.33335 (17) | 0.54984 (11) | 0.0404 (5) | |
C2 | 0.68261 (11) | 0.3336 (2) | 0.60484 (12) | 0.0483 (5) | |
H2 | 0.6913 | 0.2651 | 0.6323 | 0.058* | |
C11 | 0.70709 (15) | 0.2294 (2) | 0.38484 (14) | 0.0646 (7) | |
H11A | 0.7397 | 0.1972 | 0.3487 | 0.097* | |
H11B | 0.7348 | 0.2821 | 0.4158 | 0.097* | |
H11C | 0.6675 | 0.2736 | 0.3622 | 0.097* | |
C10 | 0.67503 (11) | 0.12915 (19) | 0.42792 (11) | 0.0430 (5) | |
N2 | 0.69504 (10) | 0.01800 (17) | 0.41311 (10) | 0.0512 (5) | |
C12 | 0.61464 (11) | 0.01774 (17) | 0.50416 (10) | 0.0369 (4) | |
C9 | 0.62300 (11) | 0.13389 (16) | 0.48535 (10) | 0.0352 (4) | |
C14 | 0.53339 (10) | 0.17653 (16) | 0.58196 (9) | 0.0328 (4) | |
C13 | 0.53320 (11) | 0.05668 (16) | 0.59824 (9) | 0.0342 (4) | |
N3 | 0.57236 (9) | −0.02562 (14) | 0.55869 (8) | 0.0410 (4) | |
H3 | 0.5702 | −0.1014 | 0.5680 | 0.049* | |
C18 | 0.49051 (12) | 0.00573 (18) | 0.66015 (10) | 0.0419 (5) | |
H18A | 0.5191 | −0.0597 | 0.6810 | 0.050* | |
H18B | 0.4440 | −0.0276 | 0.6424 | 0.050* | |
C17 | 0.47298 (12) | 0.09738 (19) | 0.71891 (10) | 0.0430 (5) | |
C16 | 0.43875 (12) | 0.20721 (19) | 0.68196 (11) | 0.0450 (5) | |
H16A | 0.3899 | 0.1854 | 0.6638 | 0.054* | |
H16B | 0.4319 | 0.2702 | 0.7175 | 0.054* | |
C15 | 0.48421 (11) | 0.25641 (17) | 0.62112 (10) | 0.0365 (4) | |
C20 | 0.54316 (14) | 0.1327 (2) | 0.75966 (12) | 0.0585 (6) | |
H20A | 0.5308 | 0.1907 | 0.7960 | 0.088* | |
H20B | 0.5786 | 0.1669 | 0.7268 | 0.088* | |
H20C | 0.5644 | 0.0626 | 0.7819 | 0.088* | |
C19 | 0.41680 (15) | 0.0438 (2) | 0.77122 (13) | 0.0644 (7) | |
H19A | 0.4374 | −0.0274 | 0.7927 | 0.097* | |
H19B | 0.3719 | 0.0235 | 0.7459 | 0.097* | |
H19C | 0.4057 | 0.1015 | 0.8081 | 0.097* | |
N1 | 0.56218 (10) | 0.41421 (14) | 0.45939 (9) | 0.0460 (4) | |
H1 | 0.5478 | 0.4654 | 0.4276 | 0.055* | |
O2 | 0.65528 (8) | −0.05644 (12) | 0.46364 (7) | 0.0470 (4) | |
O1 | 0.48047 (8) | 0.26181 (12) | 0.43288 (7) | 0.0459 (4) | |
O3 | 0.47829 (9) | 0.36227 (12) | 0.60321 (8) | 0.0500 (4) | |
Cl1 | 0.78469 (4) | 0.44523 (9) | 0.68787 (4) | 0.1018 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C3 | 0.0460 (14) | 0.0766 (19) | 0.0638 (15) | −0.0167 (13) | 0.0158 (12) | −0.0339 (14) |
C4 | 0.0681 (17) | 0.0589 (17) | 0.089 (2) | −0.0330 (14) | 0.0337 (16) | −0.0327 (15) |
C5 | 0.0736 (17) | 0.0354 (12) | 0.0744 (17) | −0.0175 (11) | 0.0311 (15) | −0.0130 (11) |
C6 | 0.0548 (13) | 0.0296 (11) | 0.0478 (11) | −0.0074 (9) | 0.0184 (10) | −0.0068 (9) |
C7 | 0.0561 (13) | 0.0227 (10) | 0.0327 (9) | 0.0033 (9) | 0.0095 (9) | 0.0017 (8) |
C8 | 0.0453 (11) | 0.0244 (9) | 0.0321 (9) | 0.0000 (8) | 0.0028 (8) | −0.0019 (7) |
C1 | 0.0475 (12) | 0.0326 (11) | 0.0413 (10) | −0.0037 (9) | 0.0102 (9) | −0.0094 (8) |
C2 | 0.0436 (12) | 0.0506 (13) | 0.0506 (12) | −0.0015 (10) | 0.0073 (10) | −0.0184 (10) |
C11 | 0.0714 (17) | 0.0578 (16) | 0.0646 (15) | −0.0068 (13) | 0.0226 (13) | −0.0022 (12) |
C10 | 0.0437 (12) | 0.0454 (13) | 0.0398 (11) | 0.0003 (10) | 0.0003 (9) | −0.0071 (9) |
N2 | 0.0558 (11) | 0.0495 (12) | 0.0484 (10) | 0.0047 (9) | 0.0043 (9) | −0.0093 (9) |
C12 | 0.0457 (12) | 0.0294 (10) | 0.0357 (10) | 0.0046 (9) | −0.0051 (9) | −0.0056 (8) |
C9 | 0.0425 (11) | 0.0297 (10) | 0.0335 (9) | 0.0007 (8) | −0.0018 (8) | −0.0038 (8) |
C14 | 0.0451 (11) | 0.0250 (9) | 0.0285 (9) | −0.0002 (8) | −0.0009 (8) | 0.0005 (7) |
C13 | 0.0445 (11) | 0.0278 (10) | 0.0303 (9) | −0.0012 (8) | −0.0061 (8) | −0.0009 (7) |
N3 | 0.0613 (11) | 0.0222 (8) | 0.0395 (9) | 0.0039 (7) | −0.0019 (8) | 0.0013 (7) |
C18 | 0.0578 (13) | 0.0302 (10) | 0.0378 (10) | −0.0050 (9) | −0.0038 (9) | 0.0073 (8) |
C17 | 0.0569 (13) | 0.0395 (11) | 0.0327 (10) | −0.0024 (10) | 0.0033 (9) | 0.0049 (8) |
C16 | 0.0541 (13) | 0.0392 (12) | 0.0418 (11) | 0.0018 (10) | 0.0077 (10) | 0.0023 (9) |
C15 | 0.0474 (11) | 0.0284 (10) | 0.0337 (9) | 0.0002 (8) | −0.0013 (9) | −0.0006 (8) |
C20 | 0.0742 (17) | 0.0651 (16) | 0.0361 (11) | −0.0030 (13) | −0.0064 (11) | −0.0025 (11) |
C19 | 0.0755 (17) | 0.0656 (16) | 0.0520 (13) | −0.0035 (13) | 0.0155 (13) | 0.0179 (12) |
N1 | 0.0712 (12) | 0.0234 (8) | 0.0433 (9) | −0.0020 (8) | 0.0098 (9) | 0.0063 (7) |
O2 | 0.0580 (9) | 0.0355 (8) | 0.0474 (8) | 0.0102 (7) | 0.0002 (7) | −0.0086 (6) |
O1 | 0.0630 (9) | 0.0329 (8) | 0.0418 (8) | −0.0007 (7) | −0.0082 (7) | 0.0052 (6) |
O3 | 0.0726 (10) | 0.0265 (7) | 0.0508 (9) | 0.0072 (7) | 0.0112 (8) | 0.0040 (6) |
Cl1 | 0.0629 (5) | 0.1486 (8) | 0.0938 (6) | −0.0320 (5) | −0.0028 (4) | −0.0515 (5) |
C3—C4 | 1.373 (4) | C12—C9 | 1.346 (3) |
C3—C2 | 1.392 (3) | C12—N3 | 1.355 (2) |
C3—Cl1 | 1.735 (3) | C14—C13 | 1.366 (2) |
C4—C5 | 1.375 (4) | C14—C15 | 1.448 (3) |
C4—H4 | 0.9300 | C13—N3 | 1.368 (2) |
C5—C6 | 1.372 (3) | C13—C18 | 1.494 (3) |
C5—H5 | 0.9300 | N3—H3 | 0.8600 |
C6—C1 | 1.387 (3) | C18—C17 | 1.527 (3) |
C6—N1 | 1.397 (3) | C18—H18A | 0.9700 |
C7—O1 | 1.220 (2) | C18—H18B | 0.9700 |
C7—N1 | 1.356 (2) | C17—C20 | 1.520 (3) |
C7—C8 | 1.555 (3) | C17—C19 | 1.522 (3) |
C8—C9 | 1.511 (3) | C17—C16 | 1.529 (3) |
C8—C1 | 1.517 (3) | C16—C15 | 1.498 (3) |
C8—C14 | 1.528 (2) | C16—H16A | 0.9700 |
C1—C2 | 1.372 (3) | C16—H16B | 0.9700 |
C2—H2 | 0.9300 | C15—O3 | 1.227 (2) |
C11—C10 | 1.488 (3) | C20—H20A | 0.9600 |
C11—H11A | 0.9600 | C20—H20B | 0.9600 |
C11—H11B | 0.9600 | C20—H20C | 0.9600 |
C11—H11C | 0.9600 | C19—H19A | 0.9600 |
C10—N2 | 1.315 (3) | C19—H19B | 0.9600 |
C10—C9 | 1.419 (3) | C19—H19C | 0.9600 |
N2—O2 | 1.441 (2) | N1—H1 | 0.8600 |
C12—O2 | 1.333 (2) | ||
C4—C3—C2 | 121.3 (2) | C15—C14—C8 | 116.57 (15) |
C4—C3—Cl1 | 119.9 (2) | C14—C13—N3 | 122.11 (17) |
C2—C3—Cl1 | 118.8 (2) | C14—C13—C18 | 122.80 (17) |
C3—C4—C5 | 121.3 (2) | N3—C13—C18 | 115.09 (16) |
C3—C4—H4 | 119.4 | C12—N3—C13 | 116.88 (15) |
C5—C4—H4 | 119.4 | C12—N3—H3 | 121.6 |
C6—C5—C4 | 117.6 (2) | C13—N3—H3 | 121.6 |
C6—C5—H5 | 121.2 | C13—C18—C17 | 113.85 (16) |
C4—C5—H5 | 121.2 | C13—C18—H18A | 108.8 |
C5—C6—C1 | 121.6 (2) | C17—C18—H18A | 108.8 |
C5—C6—N1 | 128.7 (2) | C13—C18—H18B | 108.8 |
C1—C6—N1 | 109.76 (17) | C17—C18—H18B | 108.8 |
O1—C7—N1 | 125.72 (18) | H18A—C18—H18B | 107.7 |
O1—C7—C8 | 126.47 (16) | C20—C17—C19 | 109.29 (18) |
N1—C7—C8 | 107.75 (17) | C20—C17—C18 | 111.00 (18) |
C9—C8—C1 | 113.00 (16) | C19—C17—C18 | 109.45 (18) |
C9—C8—C14 | 107.84 (15) | C20—C17—C16 | 110.52 (18) |
C1—C8—C14 | 113.66 (15) | C19—C17—C16 | 109.49 (18) |
C9—C8—C7 | 108.91 (14) | C18—C17—C16 | 107.06 (16) |
C1—C8—C7 | 101.19 (15) | C15—C16—C17 | 114.35 (17) |
C14—C8—C7 | 112.14 (15) | C15—C16—H16A | 108.7 |
C2—C1—C6 | 120.90 (19) | C17—C16—H16A | 108.7 |
C2—C1—C8 | 130.20 (19) | C15—C16—H16B | 108.7 |
C6—C1—C8 | 108.89 (18) | C17—C16—H16B | 108.7 |
C1—C2—C3 | 117.3 (2) | H16A—C16—H16B | 107.6 |
C1—C2—H2 | 121.3 | O3—C15—C14 | 120.25 (17) |
C3—C2—H2 | 121.3 | O3—C15—C16 | 120.52 (18) |
C10—C11—H11A | 109.5 | C14—C15—C16 | 119.19 (17) |
C10—C11—H11B | 109.5 | C17—C20—H20A | 109.5 |
H11A—C11—H11B | 109.5 | C17—C20—H20B | 109.5 |
C10—C11—H11C | 109.5 | H20A—C20—H20B | 109.5 |
H11A—C11—H11C | 109.5 | C17—C20—H20C | 109.5 |
H11B—C11—H11C | 109.5 | H20A—C20—H20C | 109.5 |
N2—C10—C9 | 111.83 (19) | H20B—C20—H20C | 109.5 |
N2—C10—C11 | 119.01 (19) | C17—C19—H19A | 109.5 |
C9—C10—C11 | 129.16 (19) | C17—C19—H19B | 109.5 |
C10—N2—O2 | 105.51 (16) | H19A—C19—H19B | 109.5 |
O2—C12—C9 | 112.65 (17) | C17—C19—H19C | 109.5 |
O2—C12—N3 | 120.60 (17) | H19A—C19—H19C | 109.5 |
C9—C12—N3 | 126.73 (17) | H19B—C19—H19C | 109.5 |
C12—C9—C10 | 103.49 (17) | C7—N1—C6 | 111.84 (17) |
C12—C9—C8 | 121.84 (17) | C7—N1—H1 | 124.1 |
C10—C9—C8 | 134.67 (17) | C6—N1—H1 | 124.1 |
C13—C14—C15 | 119.00 (17) | C12—O2—N2 | 106.51 (14) |
C13—C14—C8 | 124.41 (16) | ||
C2—C3—C4—C5 | 0.1 (4) | C1—C8—C9—C10 | −53.1 (3) |
Cl1—C3—C4—C5 | −178.35 (18) | C14—C8—C9—C10 | −179.6 (2) |
C3—C4—C5—C6 | −0.2 (3) | C7—C8—C9—C10 | 58.5 (3) |
C4—C5—C6—C1 | −0.3 (3) | C9—C8—C14—C13 | 2.9 (2) |
C4—C5—C6—N1 | 177.8 (2) | C1—C8—C14—C13 | −123.2 (2) |
O1—C7—C8—C9 | 65.4 (2) | C7—C8—C14—C13 | 122.75 (19) |
N1—C7—C8—C9 | −111.86 (17) | C9—C8—C14—C15 | −175.48 (16) |
O1—C7—C8—C1 | −175.38 (18) | C1—C8—C14—C15 | 58.4 (2) |
N1—C7—C8—C1 | 7.40 (18) | C7—C8—C14—C15 | −55.6 (2) |
O1—C7—C8—C14 | −53.9 (2) | C15—C14—C13—N3 | 173.17 (17) |
N1—C7—C8—C14 | 128.87 (16) | C8—C14—C13—N3 | −5.1 (3) |
C5—C6—C1—C2 | 0.9 (3) | C15—C14—C13—C18 | −6.8 (3) |
N1—C6—C1—C2 | −177.55 (17) | C8—C14—C13—C18 | 174.89 (17) |
C5—C6—C1—C8 | 179.47 (18) | O2—C12—N3—C13 | 179.11 (16) |
N1—C6—C1—C8 | 1.1 (2) | C9—C12—N3—C13 | 1.0 (3) |
C9—C8—C1—C2 | −70.3 (2) | C14—C13—N3—C12 | 3.1 (3) |
C14—C8—C1—C2 | 53.0 (3) | C18—C13—N3—C12 | −176.94 (16) |
C7—C8—C1—C2 | 173.4 (2) | C14—C13—C18—C17 | −22.5 (3) |
C9—C8—C1—C6 | 111.28 (18) | N3—C13—C18—C17 | 157.52 (17) |
C14—C8—C1—C6 | −125.39 (17) | C13—C18—C17—C20 | −70.7 (2) |
C7—C8—C1—C6 | −5.00 (19) | C13—C18—C17—C19 | 168.61 (18) |
C6—C1—C2—C3 | −0.9 (3) | C13—C18—C17—C16 | 50.0 (2) |
C8—C1—C2—C3 | −179.21 (19) | C20—C17—C16—C15 | 68.5 (2) |
C4—C3—C2—C1 | 0.5 (3) | C19—C17—C16—C15 | −171.06 (18) |
Cl1—C3—C2—C1 | 178.95 (15) | C18—C17—C16—C15 | −52.5 (2) |
C9—C10—N2—O2 | −0.7 (2) | C13—C14—C15—O3 | −173.34 (18) |
C11—C10—N2—O2 | 179.71 (19) | C8—C14—C15—O3 | 5.1 (3) |
O2—C12—C9—C10 | −0.8 (2) | C13—C14—C15—C16 | 4.5 (3) |
N3—C12—C9—C10 | 177.44 (18) | C8—C14—C15—C16 | −177.07 (17) |
O2—C12—C9—C8 | 178.75 (16) | C17—C16—C15—O3 | −155.17 (19) |
N3—C12—C9—C8 | −3.0 (3) | C17—C16—C15—C14 | 27.0 (3) |
N2—C10—C9—C12 | 1.0 (2) | O1—C7—N1—C6 | 175.33 (18) |
C11—C10—C9—C12 | −179.5 (2) | C8—C7—N1—C6 | −7.4 (2) |
N2—C10—C9—C8 | −178.5 (2) | C5—C6—N1—C7 | −174.1 (2) |
C11—C10—C9—C8 | 1.0 (4) | C1—C6—N1—C7 | 4.2 (2) |
C1—C8—C9—C12 | 127.5 (2) | C9—C12—O2—N2 | 0.4 (2) |
C14—C8—C9—C12 | 1.0 (2) | N3—C12—O2—N2 | −177.96 (16) |
C7—C8—C9—C12 | −120.92 (19) | C10—N2—O2—C12 | 0.2 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O3i | 0.86 | 2.05 | 2.837 (2) | 151 |
N3—H3···O1ii | 0.86 | 2.00 | 2.795 (2) | 153 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O3i | 0.86 | 2.05 | 2.837 (2) | 151 |
N3—H3···O1ii | 0.86 | 2.00 | 2.795 (2) | 153 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y, −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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A large number of natural products contain the quinoline and indole heterocycles, and they are found in numerous commercial products, including pharmaceuticals, fragrances and dyes (Padwa et al., 1999). In view of the above importance, crystallographic study of the title compound (I) has been carried out to establish its molecular structure.
In (I) (Fig. 1), the indole ring adopts slightly envelope conformation on atom C7. The sum of the bond angle around atom N3 (360°) of the quinoline ring indicates sp2 hybridization. The quinoline group and indole ring are in axial orientation with the dihedral angle between them as 87.39 (1)°. The indole and quinoline ring systems are planar and keto atoms O1 and O3 deviate from the attached ring system by -0.024 (1) and -0.012 (2) Å, respectively.
In the crystal, molecules are linked by two sets of N—H···O hydrogen bonds (Table 1), forming centrosymmetric dimers containing two R22(7) ring motifs (Bernstein et al., 1995).