Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680703574X/ci2423sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680703574X/ci2423Isup2.hkl |
CCDC reference: 657841
The title compound was obtained as a gift sample from Sequent Scientific Ltd, Mangalore, India. The sample was crystallized from ethyl acetate (m.p. 325–327 K).
The H atoms were included in the riding model approximation with C—H = 0.94 or 0.97 Å, and with Uiso(H) = 1.18–1.50Ueq(C). A rotating group model was used for the methyl groups. Owing to the poor diffraction quality of the crystal, the ratio of observed to unique reflections is low (43%).
Quinolines have been interesting to researchers for many years because a large number of natural products contain these heterocycles. They are found in numerous commercial products, including pharmaceuticals, fragrances and dyes. Quinoline alkaloids such as quinine, chloroquin, mefloquine and amodiaquine are used as efficient drugs for the treatment of malaria. Several quinoline derivatives have been evaluated in vitro against several parasites and HTLV-1 transformed cells. Prompted by the varied biological activities, the crystal structure of the title compound is reported.
The asymmetric unit of the title compound contains four independent molecules A, B, C and D; one of the independent molecules, A, is shown in Fig. 1. The N1—C1—C10—C11 torsion angles [(A) 1.7 (2)°, (B) 1.0 (2)°, (C) -1.0 (2)° and (D) 0.2 (2)°] indicate that the acetate group in each independent molecule is coplanar with the attached quinoline ring system.
The independent molecules exist as two pseudo inversion-related pairs (A/C and B/D). In the B/D pair the centroids of the pyridine rings are separated by a distance of 3.7181 (9) Å, indicating π-π stacking interaction. Crystal packing shows each set of these molecules form sheets parallel to the ac plane. One of the sheets is shown in Fig. 2. The sheets formed by the A/C and B/D pairs are alternately stacked along the b axis. The sheets are cross-linked by C—H···O intermolecular hydrogen-bonding interactions (Fig. 3).
For related structures, see: Lynch & McClenaghan (2001); Firley et al. (2005); Yathirajan et al. (2007). For related literature, see: Padwa et al. (1999); Robert & Meunier (1998); Franck et al. (2004).
Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C11H9NO | F(000) = 1440 |
Mr = 171.19 | Dx = 1.286 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 11806 reflections |
a = 10.3292 (4) Å | θ = 4.6–32.5° |
b = 24.1165 (9) Å | µ = 0.08 mm−1 |
c = 15.0923 (5) Å | T = 203 K |
β = 109.782 (1)° | Prism, colourless |
V = 3537.7 (2) Å3 | 0.49 × 0.41 × 0.19 mm |
Z = 16 |
Oxford Diffraction Gemini R diffractometer | 5086 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.074 |
Graphite monochromator | θmax = 32.5°, θmin = 4.6° |
φ and ω scans | h = −15→15 |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007) | k = −33→36 |
Tmin = 0.914, Tmax = 1.000 | l = −22→22 |
55457 measured reflections | 1 standard reflections every 50 reflections |
11936 independent reflections | intensity decay: none |
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)] = 0.061 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.188 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0853P)2] where P = (Fo2 + 2Fc2)/3 |
11936 reflections | (Δ/σ)max = 0.001 |
473 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
C11H9NO | V = 3537.7 (2) Å3 |
Mr = 171.19 | Z = 16 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.3292 (4) Å | µ = 0.08 mm−1 |
b = 24.1165 (9) Å | T = 203 K |
c = 15.0923 (5) Å | 0.49 × 0.41 × 0.19 mm |
β = 109.782 (1)° |
Oxford Diffraction Gemini R diffractometer | 5086 reflections with I > 2σ(I) |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007) | Rint = 0.074 |
Tmin = 0.914, Tmax = 1.000 | 1 standard reflections every 50 reflections |
55457 measured reflections | intensity decay: none |
11936 independent reflections |
R[F2 > 2σ(F2)] = 0.061 | 0 restraints |
wR(F2) = 0.188 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.26 e Å−3 |
11936 reflections | Δρmin = −0.29 e Å−3 |
473 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 | ||
O1A | −0.07703 (15) | 1.04971 (5) | 0.28167 (9) | 0.0632 (4) | |
O1B | 0.61623 (16) | 0.69661 (6) | 0.42156 (10) | 0.0748 (4) | |
O1C | 0.56572 (15) | 0.94486 (6) | 0.22088 (10) | 0.0671 (4) | |
O1D | −0.01689 (13) | 0.78006 (5) | −0.12826 (9) | 0.0606 (4) | |
N1A | 0.09636 (13) | 0.98762 (5) | 0.14437 (8) | 0.0355 (3) | |
N1B | 0.34651 (13) | 0.78162 (5) | 0.28716 (8) | 0.0373 (3) | |
N1C | 0.40511 (13) | 1.02002 (5) | 0.35393 (8) | 0.0360 (3) | |
N1D | 0.27293 (13) | 0.70810 (5) | 0.01421 (8) | 0.0357 (3) | |
C1A | 0.05158 (15) | 1.02859 (6) | 0.18400 (10) | 0.0353 (4) | |
C2A | 0.07495 (16) | 1.08525 (7) | 0.17001 (11) | 0.0406 (4) | |
H2AA | 0.0408 | 1.1131 | 0.1998 | 0.049* | |
C3A | 0.14743 (16) | 1.09886 (7) | 0.11289 (11) | 0.0401 (4) | |
H3AA | 0.1639 | 1.1363 | 0.1028 | 0.048* | |
C4A | 0.19768 (15) | 1.05654 (6) | 0.06896 (10) | 0.0334 (3) | |
C5A | 0.27301 (16) | 1.06655 (7) | 0.00820 (10) | 0.0404 (4) | |
H5AA | 0.2923 | 1.1033 | −0.0042 | 0.048* | |
C6A | 0.31811 (18) | 1.02406 (7) | −0.03262 (11) | 0.0454 (4) | |
H6AA | 0.3688 | 1.0314 | −0.0726 | 0.054* | |
C7A | 0.28899 (18) | 0.96909 (7) | −0.01509 (11) | 0.0477 (4) | |
H7AA | 0.3201 | 0.9398 | −0.0438 | 0.057* | |
C8A | 0.21618 (17) | 0.95771 (7) | 0.04305 (11) | 0.0425 (4) | |
H8AA | 0.1976 | 0.9207 | 0.0542 | 0.051* | |
C9A | 0.16879 (15) | 1.00091 (6) | 0.08646 (9) | 0.0331 (3) | |
C10A | −0.03023 (17) | 1.01341 (7) | 0.24530 (11) | 0.0410 (4) | |
C11A | −0.05311 (19) | 0.95347 (7) | 0.26026 (12) | 0.0482 (4) | |
H11A | −0.1211 | 0.9500 | 0.2912 | 0.072* | |
H11B | 0.0327 | 0.9368 | 0.2994 | 0.072* | |
H11C | −0.0858 | 0.9346 | 0.1999 | 0.072* | |
C1B | 0.40895 (18) | 0.73489 (7) | 0.32194 (10) | 0.0404 (4) | |
C2B | 0.3457 (2) | 0.68248 (7) | 0.29934 (13) | 0.0538 (5) | |
H2BA | 0.3941 | 0.6500 | 0.3253 | 0.065* | |
C3B | 0.2143 (2) | 0.67967 (8) | 0.23973 (14) | 0.0576 (5) | |
H3BA | 0.1708 | 0.6450 | 0.2245 | 0.069* | |
C4B | 0.14213 (19) | 0.72846 (7) | 0.20026 (11) | 0.0457 (4) | |
C5B | 0.0050 (2) | 0.72994 (10) | 0.13782 (14) | 0.0641 (6) | |
H5BA | −0.0446 | 0.6967 | 0.1206 | 0.077* | |
C6B | −0.0568 (2) | 0.77907 (11) | 0.10202 (14) | 0.0671 (6) | |
H6BA | −0.1480 | 0.7793 | 0.0601 | 0.080* | |
C7B | 0.01464 (19) | 0.82881 (9) | 0.12728 (12) | 0.0579 (5) | |
H7BA | −0.0285 | 0.8624 | 0.1022 | 0.069* | |
C8B | 0.14661 (18) | 0.82904 (7) | 0.18805 (11) | 0.0467 (4) | |
H8BA | 0.1936 | 0.8629 | 0.2047 | 0.056* | |
C9B | 0.21395 (17) | 0.77913 (6) | 0.22641 (10) | 0.0369 (4) | |
C10B | 0.55432 (19) | 0.73872 (8) | 0.38828 (11) | 0.0480 (4) | |
C11B | 0.6186 (2) | 0.79410 (9) | 0.41227 (14) | 0.0618 (5) | |
H11D | 0.7146 | 0.7898 | 0.4508 | 0.093* | |
H11E | 0.5711 | 0.8150 | 0.4469 | 0.093* | |
H11F | 0.6123 | 0.8138 | 0.3549 | 0.093* | |
C1C | 0.44322 (15) | 0.97599 (6) | 0.31720 (10) | 0.0346 (3) | |
C2C | 0.41114 (17) | 0.92106 (7) | 0.33494 (11) | 0.0425 (4) | |
H2CA | 0.4389 | 0.8910 | 0.3059 | 0.051* | |
C3C | 0.34016 (17) | 0.91224 (7) | 0.39416 (11) | 0.0431 (4) | |
H3CA | 0.3187 | 0.8759 | 0.4070 | 0.052* | |
C4C | 0.29849 (15) | 0.95769 (7) | 0.43651 (10) | 0.0370 (4) | |
C5C | 0.22541 (17) | 0.95245 (8) | 0.49916 (11) | 0.0473 (4) | |
H5CA | 0.2040 | 0.9169 | 0.5158 | 0.057* | |
C6C | 0.18511 (18) | 0.99770 (9) | 0.53622 (12) | 0.0534 (5) | |
H6CA | 0.1352 | 0.9934 | 0.5776 | 0.064* | |
C7C | 0.21778 (19) | 1.05106 (9) | 0.51296 (13) | 0.0568 (5) | |
H7CA | 0.1893 | 1.0823 | 0.5388 | 0.068* | |
C8C | 0.29049 (18) | 1.05791 (7) | 0.45319 (12) | 0.0487 (4) | |
H8CA | 0.3127 | 1.0938 | 0.4387 | 0.058* | |
C9C | 0.33226 (15) | 1.01170 (7) | 0.41326 (10) | 0.0359 (4) | |
C10C | 0.52527 (17) | 0.98490 (7) | 0.25350 (11) | 0.0426 (4) | |
C11C | 0.55773 (19) | 1.04276 (7) | 0.23343 (12) | 0.0482 (4) | |
H11G | 0.6110 | 1.0421 | 0.1914 | 0.072* | |
H11H | 0.6105 | 1.0609 | 0.2919 | 0.072* | |
H11I | 0.4728 | 1.0630 | 0.2039 | 0.072* | |
C1D | 0.19891 (16) | 0.75186 (6) | −0.02455 (9) | 0.0345 (3) | |
C2D | 0.24719 (18) | 0.80692 (7) | −0.00719 (11) | 0.0426 (4) | |
H2DA | 0.1905 | 0.8368 | −0.0366 | 0.051* | |
C3D | 0.37661 (19) | 0.81588 (7) | 0.05259 (11) | 0.0478 (4) | |
H3DA | 0.4104 | 0.8523 | 0.0652 | 0.057* | |
C4D | 0.46046 (17) | 0.77089 (7) | 0.09584 (10) | 0.0395 (4) | |
C5D | 0.59782 (19) | 0.77644 (9) | 0.15884 (12) | 0.0535 (5) | |
H5DA | 0.6376 | 0.8118 | 0.1732 | 0.064* | |
C6D | 0.67187 (19) | 0.73061 (9) | 0.19843 (12) | 0.0566 (5) | |
H6DA | 0.7625 | 0.7347 | 0.2402 | 0.068* | |
C7D | 0.61497 (19) | 0.67772 (9) | 0.17777 (12) | 0.0551 (5) | |
H7DA | 0.6676 | 0.6466 | 0.2061 | 0.066* | |
C8D | 0.48436 (17) | 0.67053 (7) | 0.11711 (11) | 0.0442 (4) | |
H8DA | 0.4476 | 0.6346 | 0.1036 | 0.053* | |
C9D | 0.40373 (16) | 0.71704 (6) | 0.07426 (10) | 0.0365 (4) | |
C10D | 0.05534 (17) | 0.74153 (7) | −0.09018 (10) | 0.0403 (4) | |
C11D | 0.00576 (19) | 0.68309 (8) | −0.10771 (14) | 0.0571 (5) | |
H11J | −0.0888 | 0.6828 | −0.1502 | 0.086* | |
H11K | 0.0107 | 0.6659 | −0.0486 | 0.086* | |
H11L | 0.0631 | 0.6627 | −0.1357 | 0.086* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1A | 0.0817 (10) | 0.0495 (8) | 0.0786 (9) | 0.0120 (7) | 0.0535 (8) | 0.0025 (6) |
O1B | 0.0790 (10) | 0.0721 (10) | 0.0684 (9) | 0.0381 (8) | 0.0186 (8) | 0.0202 (7) |
O1C | 0.0861 (10) | 0.0576 (9) | 0.0776 (9) | −0.0007 (7) | 0.0538 (8) | −0.0101 (7) |
O1D | 0.0498 (8) | 0.0568 (8) | 0.0599 (8) | 0.0169 (6) | −0.0014 (6) | −0.0007 (6) |
N1A | 0.0360 (7) | 0.0342 (7) | 0.0349 (6) | 0.0040 (6) | 0.0100 (6) | 0.0010 (5) |
N1B | 0.0383 (8) | 0.0360 (7) | 0.0369 (7) | 0.0031 (6) | 0.0117 (6) | −0.0001 (5) |
N1C | 0.0356 (7) | 0.0375 (7) | 0.0352 (6) | −0.0034 (6) | 0.0122 (6) | 0.0005 (5) |
N1D | 0.0356 (7) | 0.0386 (7) | 0.0325 (6) | 0.0060 (6) | 0.0112 (6) | −0.0005 (5) |
C1A | 0.0325 (8) | 0.0378 (9) | 0.0332 (7) | 0.0025 (7) | 0.0080 (7) | −0.0007 (6) |
C2A | 0.0434 (9) | 0.0357 (9) | 0.0417 (8) | 0.0046 (7) | 0.0133 (8) | −0.0058 (7) |
C3A | 0.0424 (9) | 0.0312 (8) | 0.0445 (9) | −0.0023 (7) | 0.0119 (8) | −0.0025 (7) |
C4A | 0.0289 (8) | 0.0355 (8) | 0.0316 (7) | −0.0007 (6) | 0.0045 (6) | 0.0000 (6) |
C5A | 0.0353 (9) | 0.0428 (9) | 0.0403 (8) | −0.0051 (7) | 0.0092 (7) | 0.0037 (7) |
C6A | 0.0427 (10) | 0.0561 (11) | 0.0388 (8) | 0.0042 (8) | 0.0157 (8) | 0.0058 (8) |
C7A | 0.0542 (11) | 0.0474 (10) | 0.0461 (9) | 0.0133 (9) | 0.0229 (9) | −0.0018 (8) |
C8A | 0.0485 (10) | 0.0355 (9) | 0.0459 (9) | 0.0075 (7) | 0.0190 (8) | −0.0002 (7) |
C9A | 0.0322 (8) | 0.0350 (8) | 0.0284 (7) | 0.0034 (6) | 0.0057 (6) | 0.0015 (6) |
C10A | 0.0401 (9) | 0.0430 (10) | 0.0406 (8) | 0.0069 (7) | 0.0144 (7) | 0.0033 (7) |
C11A | 0.0561 (11) | 0.0457 (10) | 0.0482 (9) | 0.0046 (8) | 0.0248 (9) | 0.0074 (8) |
C1B | 0.0524 (10) | 0.0382 (9) | 0.0368 (8) | 0.0079 (8) | 0.0232 (8) | 0.0019 (7) |
C2B | 0.0767 (14) | 0.0375 (10) | 0.0551 (10) | 0.0043 (9) | 0.0326 (11) | 0.0004 (8) |
C3B | 0.0812 (15) | 0.0402 (10) | 0.0643 (11) | −0.0196 (10) | 0.0414 (11) | −0.0133 (9) |
C4B | 0.0524 (11) | 0.0506 (11) | 0.0424 (9) | −0.0134 (8) | 0.0269 (9) | −0.0115 (8) |
C5B | 0.0569 (13) | 0.0849 (16) | 0.0556 (11) | −0.0321 (12) | 0.0258 (11) | −0.0266 (11) |
C6B | 0.0388 (11) | 0.1102 (19) | 0.0487 (11) | −0.0032 (12) | 0.0102 (9) | −0.0180 (11) |
C7B | 0.0441 (11) | 0.0798 (15) | 0.0437 (9) | 0.0137 (10) | 0.0069 (9) | −0.0084 (9) |
C8B | 0.0430 (10) | 0.0488 (10) | 0.0447 (9) | 0.0045 (8) | 0.0100 (8) | −0.0019 (8) |
C9B | 0.0392 (9) | 0.0420 (9) | 0.0332 (7) | −0.0016 (7) | 0.0170 (7) | −0.0049 (6) |
C10B | 0.0516 (11) | 0.0562 (11) | 0.0388 (8) | 0.0187 (9) | 0.0186 (8) | 0.0082 (8) |
C11B | 0.0444 (11) | 0.0722 (14) | 0.0578 (11) | 0.0055 (10) | 0.0028 (9) | 0.0006 (10) |
C1C | 0.0301 (8) | 0.0373 (9) | 0.0345 (7) | −0.0012 (6) | 0.0084 (7) | 0.0014 (6) |
C2C | 0.0456 (10) | 0.0379 (9) | 0.0428 (8) | −0.0018 (7) | 0.0133 (8) | −0.0004 (7) |
C3C | 0.0436 (9) | 0.0360 (9) | 0.0458 (9) | −0.0073 (7) | 0.0100 (8) | 0.0022 (7) |
C4C | 0.0290 (8) | 0.0460 (9) | 0.0328 (8) | −0.0061 (7) | 0.0061 (7) | 0.0033 (7) |
C5C | 0.0406 (9) | 0.0557 (11) | 0.0439 (9) | −0.0111 (8) | 0.0120 (8) | 0.0040 (8) |
C6C | 0.0397 (10) | 0.0794 (14) | 0.0435 (9) | −0.0074 (9) | 0.0172 (8) | −0.0014 (9) |
C7C | 0.0541 (11) | 0.0648 (13) | 0.0555 (11) | 0.0047 (10) | 0.0237 (10) | −0.0120 (9) |
C8C | 0.0542 (11) | 0.0469 (10) | 0.0495 (9) | −0.0042 (8) | 0.0235 (9) | −0.0036 (8) |
C9C | 0.0284 (8) | 0.0426 (9) | 0.0322 (7) | −0.0030 (7) | 0.0043 (7) | 0.0003 (6) |
C10C | 0.0420 (9) | 0.0483 (10) | 0.0385 (8) | −0.0011 (8) | 0.0149 (8) | −0.0025 (7) |
C11C | 0.0487 (10) | 0.0552 (11) | 0.0438 (9) | −0.0046 (9) | 0.0196 (8) | 0.0072 (8) |
C1D | 0.0370 (8) | 0.0398 (9) | 0.0282 (7) | 0.0071 (7) | 0.0129 (7) | −0.0014 (6) |
C2D | 0.0503 (10) | 0.0360 (9) | 0.0406 (8) | 0.0086 (8) | 0.0142 (8) | −0.0001 (7) |
C3D | 0.0532 (11) | 0.0402 (9) | 0.0477 (9) | −0.0040 (8) | 0.0138 (9) | −0.0057 (7) |
C4D | 0.0378 (9) | 0.0488 (10) | 0.0338 (8) | 0.0004 (7) | 0.0144 (7) | −0.0032 (7) |
C5D | 0.0424 (10) | 0.0699 (13) | 0.0458 (10) | −0.0072 (9) | 0.0116 (9) | −0.0077 (9) |
C6D | 0.0329 (9) | 0.0939 (16) | 0.0384 (9) | 0.0066 (10) | 0.0062 (8) | −0.0008 (10) |
C7D | 0.0491 (11) | 0.0734 (14) | 0.0414 (9) | 0.0198 (10) | 0.0133 (9) | 0.0068 (9) |
C8D | 0.0428 (10) | 0.0514 (10) | 0.0382 (8) | 0.0123 (8) | 0.0135 (8) | 0.0036 (7) |
C9D | 0.0345 (8) | 0.0452 (9) | 0.0318 (7) | 0.0062 (7) | 0.0140 (7) | 0.0011 (6) |
C10D | 0.0385 (9) | 0.0466 (10) | 0.0351 (8) | 0.0067 (8) | 0.0116 (7) | −0.0041 (7) |
C11D | 0.0453 (11) | 0.0532 (11) | 0.0646 (11) | −0.0002 (9) | 0.0077 (9) | −0.0086 (9) |
O1A—C10A | 1.2170 (19) | C8B—C9B | 1.412 (2) |
O1B—C10B | 1.214 (2) | C8B—H8BA | 0.94 |
O1C—C10C | 1.220 (2) | C10B—C11B | 1.481 (3) |
O1D—C10D | 1.2084 (18) | C11B—H11D | 0.97 |
N1A—C1A | 1.3173 (19) | C11B—H11E | 0.97 |
N1A—C9A | 1.3671 (19) | C11B—H11F | 0.97 |
N1B—C1B | 1.3162 (19) | C1C—C2C | 1.413 (2) |
N1B—C9B | 1.367 (2) | C1C—C10C | 1.497 (2) |
N1C—C1C | 1.318 (2) | C2C—C3C | 1.351 (2) |
N1C—C9C | 1.3653 (19) | C2C—H2CA | 0.94 |
N1D—C1D | 1.3183 (19) | C3C—C4C | 1.408 (2) |
N1D—C9D | 1.3654 (19) | C3C—H3CA | 0.94 |
C1A—C2A | 1.416 (2) | C4C—C5C | 1.401 (2) |
C1A—C10A | 1.494 (2) | C4C—C9C | 1.423 (2) |
C2A—C3A | 1.360 (2) | C5C—C6C | 1.354 (3) |
C2A—H2AA | 0.94 | C5C—H5CA | 0.94 |
C3A—C4A | 1.408 (2) | C6C—C7C | 1.405 (3) |
C3A—H3AA | 0.94 | C6C—H6CA | 0.94 |
C4A—C5A | 1.410 (2) | C7C—C8C | 1.365 (2) |
C4A—C9A | 1.419 (2) | C7C—H7CA | 0.94 |
C5A—C6A | 1.357 (2) | C8C—C9C | 1.403 (2) |
C5A—H5AA | 0.94 | C8C—H8CA | 0.94 |
C6A—C7A | 1.404 (2) | C10C—C11C | 1.490 (2) |
C6A—H6AA | 0.94 | C11C—H11G | 0.97 |
C7A—C8A | 1.363 (2) | C11C—H11H | 0.97 |
C7A—H7AA | 0.94 | C11C—H11I | 0.97 |
C8A—C9A | 1.404 (2) | C1D—C2D | 1.411 (2) |
C8A—H8AA | 0.94 | C1D—C10D | 1.499 (2) |
C10A—C11A | 1.494 (2) | C2D—C3D | 1.353 (2) |
C11A—H11A | 0.97 | C2D—H2DA | 0.94 |
C11A—H11B | 0.97 | C3D—C4D | 1.404 (2) |
C11A—H11C | 0.97 | C3D—H3DA | 0.94 |
C1B—C2B | 1.411 (2) | C4D—C9D | 1.417 (2) |
C1B—C10B | 1.499 (2) | C4D—C5D | 1.422 (2) |
C2B—C3B | 1.352 (3) | C5D—C6D | 1.362 (3) |
C2B—H2BA | 0.94 | C5D—H5DA | 0.94 |
C3B—C4B | 1.413 (3) | C6D—C7D | 1.395 (3) |
C3B—H3BA | 0.94 | C6D—H6DA | 0.94 |
C4B—C5B | 1.411 (3) | C7D—C8D | 1.361 (2) |
C4B—C9B | 1.415 (2) | C7D—H7DA | 0.94 |
C5B—C6B | 1.367 (3) | C8D—C9D | 1.416 (2) |
C5B—H5BA | 0.94 | C8D—H8DA | 0.94 |
C6B—C7B | 1.392 (3) | C10D—C11D | 1.492 (2) |
C6B—H6BA | 0.94 | C11D—H11J | 0.97 |
C7B—C8B | 1.361 (2) | C11D—H11K | 0.97 |
C7B—H7BA | 0.94 | C11D—H11L | 0.97 |
C1A—N1A—C9A | 117.82 (13) | H11D—C11B—H11F | 109.5 |
C1B—N1B—C9B | 118.31 (14) | H11E—C11B—H11F | 109.5 |
C1C—N1C—C9C | 117.83 (13) | N1C—C1C—C2C | 123.57 (15) |
C1D—N1D—C9D | 117.59 (14) | N1C—C1C—C10C | 117.99 (14) |
N1A—C1A—C2A | 123.53 (15) | C2C—C1C—C10C | 118.44 (15) |
N1A—C1A—C10A | 117.15 (14) | C3C—C2C—C1C | 119.18 (16) |
C2A—C1A—C10A | 119.31 (14) | C3C—C2C—H2CA | 120.4 |
C3A—C2A—C1A | 119.06 (15) | C1C—C2C—H2CA | 120.4 |
C3A—C2A—H2AA | 120.5 | C2C—C3C—C4C | 119.70 (15) |
C1A—C2A—H2AA | 120.5 | C2C—C3C—H3CA | 120.1 |
C2A—C3A—C4A | 119.57 (15) | C4C—C3C—H3CA | 120.1 |
C2A—C3A—H3AA | 120.2 | C5C—C4C—C3C | 123.61 (15) |
C4A—C3A—H3AA | 120.2 | C5C—C4C—C9C | 118.82 (15) |
C3A—C4A—C5A | 123.68 (14) | C3C—C4C—C9C | 117.57 (14) |
C3A—C4A—C9A | 117.61 (14) | C6C—C5C—C4C | 121.14 (17) |
C5A—C4A—C9A | 118.70 (14) | C6C—C5C—H5CA | 119.4 |
C6A—C5A—C4A | 121.06 (15) | C4C—C5C—H5CA | 119.4 |
C6A—C5A—H5AA | 119.5 | C5C—C6C—C7C | 120.09 (18) |
C4A—C5A—H5AA | 119.5 | C5C—C6C—H6CA | 120.0 |
C5A—C6A—C7A | 119.94 (16) | C7C—C6C—H6CA | 120.0 |
C5A—C6A—H6AA | 120.0 | C8C—C7C—C6C | 120.56 (18) |
C7A—C6A—H6AA | 120.0 | C8C—C7C—H7CA | 119.7 |
C8A—C7A—C6A | 120.76 (16) | C6C—C7C—H7CA | 119.7 |
C8A—C7A—H7AA | 119.6 | C7C—C8C—C9C | 120.39 (17) |
C6A—C7A—H7AA | 119.6 | C7C—C8C—H8CA | 119.8 |
C7A—C8A—C9A | 120.43 (16) | C9C—C8C—H8CA | 119.8 |
C7A—C8A—H8AA | 119.8 | N1C—C9C—C8C | 118.89 (15) |
C9A—C8A—H8AA | 119.8 | N1C—C9C—C4C | 122.12 (14) |
N1A—C9A—C8A | 118.49 (14) | C8C—C9C—C4C | 118.99 (15) |
N1A—C9A—C4A | 122.41 (13) | O1C—C10C—C11C | 121.86 (16) |
C8A—C9A—C4A | 119.10 (14) | O1C—C10C—C1C | 119.43 (16) |
O1A—C10A—C11A | 121.36 (16) | C11C—C10C—C1C | 118.70 (15) |
O1A—C10A—C1A | 119.82 (15) | C10C—C11C—H11G | 109.5 |
C11A—C10A—C1A | 118.83 (14) | C10C—C11C—H11H | 109.5 |
C10A—C11A—H11A | 109.5 | H11G—C11C—H11H | 109.5 |
C10A—C11A—H11B | 109.5 | C10C—C11C—H11I | 109.5 |
H11A—C11A—H11B | 109.5 | H11G—C11C—H11I | 109.5 |
C10A—C11A—H11C | 109.5 | H11H—C11C—H11I | 109.5 |
H11A—C11A—H11C | 109.5 | N1D—C1D—C2D | 123.74 (14) |
H11B—C11A—H11C | 109.5 | N1D—C1D—C10D | 117.10 (14) |
N1B—C1B—C2B | 123.13 (17) | C2D—C1D—C10D | 119.16 (14) |
N1B—C1B—C10B | 117.29 (15) | C3D—C2D—C1D | 118.76 (15) |
C2B—C1B—C10B | 119.58 (16) | C3D—C2D—H2DA | 120.6 |
C3B—C2B—C1B | 118.95 (17) | C1D—C2D—H2DA | 120.6 |
C3B—C2B—H2BA | 120.5 | C2D—C3D—C4D | 120.10 (16) |
C1B—C2B—H2BA | 120.5 | C2D—C3D—H3DA | 120.0 |
C2B—C3B—C4B | 120.43 (17) | C4D—C3D—H3DA | 120.0 |
C2B—C3B—H3BA | 119.8 | C3D—C4D—C9D | 117.36 (15) |
C4B—C3B—H3BA | 119.8 | C3D—C4D—C5D | 123.86 (16) |
C5B—C4B—C3B | 124.74 (18) | C9D—C4D—C5D | 118.78 (16) |
C5B—C4B—C9B | 118.52 (18) | C6D—C5D—C4D | 120.14 (18) |
C3B—C4B—C9B | 116.73 (17) | C6D—C5D—H5DA | 119.9 |
C6B—C5B—C4B | 120.96 (19) | C4D—C5D—H5DA | 119.9 |
C6B—C5B—H5BA | 119.5 | C5D—C6D—C7D | 120.83 (17) |
C4B—C5B—H5BA | 119.5 | C5D—C6D—H6DA | 119.6 |
C5B—C6B—C7B | 120.34 (19) | C7D—C6D—H6DA | 119.6 |
C5B—C6B—H6BA | 119.8 | C8D—C7D—C6D | 120.91 (17) |
C7B—C6B—H6BA | 119.8 | C8D—C7D—H7DA | 119.5 |
C8B—C7B—C6B | 120.33 (19) | C6D—C7D—H7DA | 119.5 |
C8B—C7B—H7BA | 119.8 | C7D—C8D—C9D | 120.14 (17) |
C6B—C7B—H7BA | 119.8 | C7D—C8D—H8DA | 119.9 |
C7B—C8B—C9B | 120.97 (17) | C9D—C8D—H8DA | 119.9 |
C7B—C8B—H8BA | 119.5 | N1D—C9D—C8D | 118.36 (15) |
C9B—C8B—H8BA | 119.5 | N1D—C9D—C4D | 122.46 (14) |
N1B—C9B—C8B | 118.68 (14) | C8D—C9D—C4D | 119.18 (15) |
N1B—C9B—C4B | 122.45 (15) | O1D—C10D—C11D | 121.49 (15) |
C8B—C9B—C4B | 118.86 (16) | O1D—C10D—C1D | 119.99 (15) |
O1B—C10B—C11B | 121.54 (18) | C11D—C10D—C1D | 118.52 (14) |
O1B—C10B—C1B | 119.53 (18) | C10D—C11D—H11J | 109.5 |
C11B—C10B—C1B | 118.93 (15) | C10D—C11D—H11K | 109.5 |
C10B—C11B—H11D | 109.5 | H11J—C11D—H11K | 109.5 |
C10B—C11B—H11E | 109.5 | C10D—C11D—H11L | 109.5 |
H11D—C11B—H11E | 109.5 | H11J—C11D—H11L | 109.5 |
C10B—C11B—H11F | 109.5 | H11K—C11D—H11L | 109.5 |
C9A—N1A—C1A—C2A | −0.2 (2) | C9C—N1C—C1C—C2C | 0.9 (2) |
C9A—N1A—C1A—C10A | 178.60 (12) | C9C—N1C—C1C—C10C | −178.92 (13) |
N1A—C1A—C2A—C3A | −0.1 (2) | N1C—C1C—C2C—C3C | −1.5 (2) |
C10A—C1A—C2A—C3A | −178.89 (14) | C10C—C1C—C2C—C3C | 178.34 (14) |
C1A—C2A—C3A—C4A | 0.0 (2) | C1C—C2C—C3C—C4C | 0.5 (2) |
C2A—C3A—C4A—C5A | 179.59 (14) | C2C—C3C—C4C—C5C | −179.58 (15) |
C2A—C3A—C4A—C9A | 0.4 (2) | C2C—C3C—C4C—C9C | 0.9 (2) |
C3A—C4A—C5A—C6A | −179.58 (15) | C3C—C4C—C5C—C6C | −178.47 (15) |
C9A—C4A—C5A—C6A | −0.4 (2) | C9C—C4C—C5C—C6C | 1.1 (2) |
C4A—C5A—C6A—C7A | 0.5 (2) | C4C—C5C—C6C—C7C | −0.8 (3) |
C5A—C6A—C7A—C8A | −0.3 (3) | C5C—C6C—C7C—C8C | −0.2 (3) |
C6A—C7A—C8A—C9A | 0.1 (2) | C6C—C7C—C8C—C9C | 0.8 (3) |
C1A—N1A—C9A—C8A | −179.46 (13) | C1C—N1C—C9C—C8C | −179.97 (14) |
C1A—N1A—C9A—C4A | 0.6 (2) | C1C—N1C—C9C—C4C | 0.6 (2) |
C7A—C8A—C9A—N1A | −179.89 (14) | C7C—C8C—C9C—N1C | −179.86 (15) |
C7A—C8A—C9A—C4A | 0.0 (2) | C7C—C8C—C9C—C4C | −0.4 (2) |
C3A—C4A—C9A—N1A | −0.7 (2) | C5C—C4C—C9C—N1C | 178.95 (13) |
C5A—C4A—C9A—N1A | −179.96 (13) | C3C—C4C—C9C—N1C | −1.5 (2) |
C3A—C4A—C9A—C8A | 179.38 (13) | C5C—C4C—C9C—C8C | −0.5 (2) |
C5A—C4A—C9A—C8A | 0.1 (2) | C3C—C4C—C9C—C8C | 179.09 (14) |
N1A—C1A—C10A—O1A | −178.13 (15) | N1C—C1C—C10C—O1C | 177.67 (15) |
C2A—C1A—C10A—O1A | 0.8 (2) | C2C—C1C—C10C—O1C | −2.2 (2) |
N1A—C1A—C10A—C11A | 1.7 (2) | N1C—C1C—C10C—C11C | −1.0 (2) |
C2A—C1A—C10A—C11A | −179.44 (14) | C2C—C1C—C10C—C11C | 179.15 (14) |
C9B—N1B—C1B—C2B | 0.2 (2) | C9D—N1D—C1D—C2D | −0.2 (2) |
C9B—N1B—C1B—C10B | 179.92 (13) | C9D—N1D—C1D—C10D | −179.85 (12) |
N1B—C1B—C2B—C3B | −0.5 (3) | N1D—C1D—C2D—C3D | −0.1 (2) |
C10B—C1B—C2B—C3B | 179.72 (15) | C10D—C1D—C2D—C3D | 179.60 (14) |
C1B—C2B—C3B—C4B | 0.5 (3) | C1D—C2D—C3D—C4D | 0.2 (2) |
C2B—C3B—C4B—C5B | −179.74 (17) | C2D—C3D—C4D—C9D | −0.1 (2) |
C2B—C3B—C4B—C9B | −0.1 (3) | C2D—C3D—C4D—C5D | 179.46 (16) |
C3B—C4B—C5B—C6B | −179.29 (18) | C3D—C4D—C5D—C6D | 179.45 (16) |
C9B—C4B—C5B—C6B | 1.0 (3) | C9D—C4D—C5D—C6D | −1.0 (2) |
C4B—C5B—C6B—C7B | −0.5 (3) | C4D—C5D—C6D—C7D | 0.3 (3) |
C5B—C6B—C7B—C8B | −0.2 (3) | C5D—C6D—C7D—C8D | 0.4 (3) |
C6B—C7B—C8B—C9B | 0.2 (3) | C6D—C7D—C8D—C9D | −0.3 (3) |
C1B—N1B—C9B—C8B | −179.41 (14) | C1D—N1D—C9D—C8D | 179.52 (13) |
C1B—N1B—C9B—C4B | 0.3 (2) | C1D—N1D—C9D—C4D | 0.3 (2) |
C7B—C8B—C9B—N1B | −179.98 (15) | C7D—C8D—C9D—N1D | −179.66 (14) |
C7B—C8B—C9B—C4B | 0.3 (2) | C7D—C8D—C9D—C4D | −0.4 (2) |
C5B—C4B—C9B—N1B | 179.38 (14) | C3D—C4D—C9D—N1D | −0.1 (2) |
C3B—C4B—C9B—N1B | −0.3 (2) | C5D—C4D—C9D—N1D | −179.74 (14) |
C5B—C4B—C9B—C8B | −0.9 (2) | C3D—C4D—C9D—C8D | −179.36 (14) |
C3B—C4B—C9B—C8B | 179.36 (15) | C5D—C4D—C9D—C8D | 1.0 (2) |
N1B—C1B—C10B—O1B | −179.49 (15) | N1D—C1D—C10D—O1D | −179.47 (14) |
C2B—C1B—C10B—O1B | 0.3 (2) | C2D—C1D—C10D—O1D | 0.8 (2) |
N1B—C1B—C10B—C11B | 1.0 (2) | N1D—C1D—C10D—C11D | −0.2 (2) |
C2B—C1B—C10B—C11B | −179.21 (16) | C2D—C1D—C10D—C11D | −179.92 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
C3B—H3BA···O1Ai | 0.94 | 2.48 | 3.410 (2) | 169 |
C6D—H6DA···O1Dii | 0.94 | 2.49 | 3.399 (2) | 163 |
Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) x+1, −y+3/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C11H9NO |
Mr | 171.19 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 203 |
a, b, c (Å) | 10.3292 (4), 24.1165 (9), 15.0923 (5) |
β (°) | 109.782 (1) |
V (Å3) | 3537.7 (2) |
Z | 16 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.49 × 0.41 × 0.19 |
Data collection | |
Diffractometer | Oxford Diffraction Gemini R |
Absorption correction | Multi-scan (CrysAlis PRO; Oxford Diffraction, 2007) |
Tmin, Tmax | 0.914, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 55457, 11936, 5086 |
Rint | 0.074 |
(sin θ/λ)max (Å−1) | 0.757 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.061, 0.188, 1.01 |
No. of reflections | 11936 |
No. of parameters | 473 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.26, −0.29 |
Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), CrysAlis PRO, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
C3B—H3BA···O1Ai | 0.94 | 2.48 | 3.410 (2) | 169 |
C6D—H6DA···O1Dii | 0.94 | 2.49 | 3.399 (2) | 163 |
Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) x+1, −y+3/2, z+1/2. |
Quinolines have been interesting to researchers for many years because a large number of natural products contain these heterocycles. They are found in numerous commercial products, including pharmaceuticals, fragrances and dyes. Quinoline alkaloids such as quinine, chloroquin, mefloquine and amodiaquine are used as efficient drugs for the treatment of malaria. Several quinoline derivatives have been evaluated in vitro against several parasites and HTLV-1 transformed cells. Prompted by the varied biological activities, the crystal structure of the title compound is reported.
The asymmetric unit of the title compound contains four independent molecules A, B, C and D; one of the independent molecules, A, is shown in Fig. 1. The N1—C1—C10—C11 torsion angles [(A) 1.7 (2)°, (B) 1.0 (2)°, (C) -1.0 (2)° and (D) 0.2 (2)°] indicate that the acetate group in each independent molecule is coplanar with the attached quinoline ring system.
The independent molecules exist as two pseudo inversion-related pairs (A/C and B/D). In the B/D pair the centroids of the pyridine rings are separated by a distance of 3.7181 (9) Å, indicating π-π stacking interaction. Crystal packing shows each set of these molecules form sheets parallel to the ac plane. One of the sheets is shown in Fig. 2. The sheets formed by the A/C and B/D pairs are alternately stacked along the b axis. The sheets are cross-linked by C—H···O intermolecular hydrogen-bonding interactions (Fig. 3).