Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807034769/ci2417sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807034769/ci2417Isup2.hkl |
CCDC reference: 657808
Key indicators
- Single-crystal X-ray study
- T = 203 K
- Mean (C-C) = 0.002 Å
- R factor = 0.049
- wR factor = 0.114
- Data-to-parameter ratio = 24.0
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 31 Perc.
Alert level C GOODF01_ALERT_2_C The least squares goodness of fit parameter lies outside the range 0.80 <> 2.00 Goodness of fit given = 0.752
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related structures, see: Lynch & McClenaghan (2001); Firley et al. (2005); Yathirajan et al. (2007). For related literature, see: Robert & Meunier (1998); Padwa et al. (1999); Franck et al. (2004).
The title compound was obtained as a gift sample from Sequent Scientific Ltd, Mangalore, India. The sample was crystallized from methanol (m.p. 341–343 K).
The H atoms were included in the riding model approximation with C—H = 0.94 or 0.97 Å, and with Uiso(H) = 1.18–1.49Ueq(C). Owing to the poor diffraction quality of the crystal, the ratio of observed to unique reflections is low (31%).
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 (Fig. 1).
One acetyl group is coplanar with the quinoline ring system, with a N—C1—C10—O1 torsion angle of -178.24 (14) Å, while the second is slightly twisted out of the plane, with a C2—C3—C12—C13 torsion angle of -20.9 (2)°.
Intermolecular C—H···O hydrogen bonding interactions involving the H13A and H13B methyl hydrogen atoms and acetyl oxygen atoms O1 and O2 link the molecules into a ribbon (Fig. 2). In addition, the crystal structure is stabilized by π-π stacking interactions between the pyridine rings of the inversion-related molecules at (x, y, z) and (-x, -y, -z), with the ring centroids separated by 3.5246 (9) Å.
For related structures, see: Lynch & McClenaghan (2001); Firley et al. (2005); Yathirajan et al. (2007). For related literature, see: Robert & Meunier (1998); Padwa et al. (1999); 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).
C13H11NO2 | F(000) = 448 |
Mr = 213.23 | Dx = 1.337 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 1840 reflections |
a = 7.5285 (6) Å | θ = 4.6–32.5° |
b = 15.0366 (12) Å | µ = 0.09 mm−1 |
c = 9.7202 (7) Å | T = 203 K |
β = 105.704 (9)° | Prism, pale yellow |
V = 1059.28 (14) Å3 | 0.57 × 0.43 × 0.41 mm |
Z = 4 |
Oxford Diffraction Gemini R diffractometer | 1078 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.058 |
Graphite monochromator | θmax = 32.6°, θmin = 4.6° |
Detector resolution: 10.5081 pixels mm-1 | h = −11→11 |
φ and ω scans | k = −22→19 |
9975 measured reflections | l = −14→14 |
3533 independent reflections |
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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.114 | H-atom parameters constrained |
S = 0.75 | w = 1/[σ2(Fo2) + (0.0508P)2] where P = (Fo2 + 2Fc2)/3 |
3533 reflections | (Δ/σ)max = 0.001 |
147 parameters | Δρmax = 0.29 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
C13H11NO2 | V = 1059.28 (14) Å3 |
Mr = 213.23 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 7.5285 (6) Å | µ = 0.09 mm−1 |
b = 15.0366 (12) Å | T = 203 K |
c = 9.7202 (7) Å | 0.57 × 0.43 × 0.41 mm |
β = 105.704 (9)° |
Oxford Diffraction Gemini R diffractometer | 1078 reflections with I > 2σ(I) |
9975 measured reflections | Rint = 0.058 |
3533 independent reflections |
R[F2 > 2σ(F2)] = 0.049 | 0 restraints |
wR(F2) = 0.114 | H-atom parameters constrained |
S = 0.75 | Δρmax = 0.29 e Å−3 |
3533 reflections | Δρmin = −0.20 e Å−3 |
147 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 | ||
O1 | −0.19345 (15) | 0.03032 (8) | −0.46646 (11) | 0.0490 (3) | |
O2 | 0.25235 (18) | 0.21491 (9) | 0.09646 (12) | 0.0755 (5) | |
N | 0.09472 (16) | −0.07751 (9) | −0.17029 (12) | 0.0350 (3) | |
C1 | 0.0180 (2) | −0.00917 (10) | −0.24815 (15) | 0.0327 (4) | |
C2 | 0.05337 (19) | 0.07988 (11) | −0.20552 (15) | 0.0337 (4) | |
H2 | −0.0049 | 0.1260 | −0.2664 | 0.040* | |
C3 | 0.17264 (19) | 0.09967 (10) | −0.07536 (15) | 0.0322 (4) | |
C4 | 0.26019 (19) | 0.02745 (11) | 0.01274 (15) | 0.0313 (4) | |
C5 | 0.3888 (2) | 0.03630 (11) | 0.14916 (16) | 0.0384 (4) | |
H5 | 0.4245 | 0.0934 | 0.1858 | 0.046* | |
C6 | 0.4609 (2) | −0.03655 (12) | 0.22760 (17) | 0.0432 (4) | |
H6 | 0.5448 | −0.0290 | 0.3180 | 0.052* | |
C7 | 0.4124 (2) | −0.12220 (12) | 0.17607 (17) | 0.0444 (5) | |
H7 | 0.4613 | −0.1718 | 0.2324 | 0.053* | |
C8 | 0.2942 (2) | −0.13380 (11) | 0.04399 (17) | 0.0408 (4) | |
H8 | 0.2644 | −0.1916 | 0.0085 | 0.049* | |
C9 | 0.21614 (19) | −0.06001 (10) | −0.03993 (15) | 0.0327 (4) | |
C10 | −0.1207 (2) | −0.02998 (11) | −0.38780 (16) | 0.0375 (4) | |
C11 | −0.1623 (2) | −0.12551 (11) | −0.42487 (18) | 0.0516 (5) | |
H11A | −0.2681 | −0.1296 | −0.5079 | 0.077* | |
H11B | −0.1896 | −0.1557 | −0.3448 | 0.077* | |
H11C | −0.0564 | −0.1532 | −0.4460 | 0.077* | |
C12 | 0.1988 (2) | 0.19507 (11) | −0.02893 (17) | 0.0424 (4) | |
C13 | 0.1504 (2) | 0.26635 (12) | −0.13877 (18) | 0.0595 (5) | |
H13A | 0.1814 | 0.3238 | −0.0933 | 0.089* | |
H13B | 0.0192 | 0.2642 | −0.1856 | 0.089* | |
H13C | 0.2190 | 0.2576 | −0.2090 | 0.089* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0586 (8) | 0.0419 (8) | 0.0376 (7) | 0.0030 (6) | −0.0023 (6) | 0.0038 (6) |
O2 | 0.1174 (11) | 0.0434 (9) | 0.0470 (8) | 0.0042 (8) | −0.0099 (7) | −0.0099 (7) |
N | 0.0388 (7) | 0.0316 (8) | 0.0335 (7) | −0.0013 (6) | 0.0077 (6) | 0.0007 (6) |
C1 | 0.0387 (9) | 0.0292 (9) | 0.0292 (9) | −0.0001 (7) | 0.0075 (7) | 0.0021 (7) |
C2 | 0.0374 (9) | 0.0323 (9) | 0.0308 (9) | 0.0025 (7) | 0.0084 (7) | 0.0042 (7) |
C3 | 0.0362 (9) | 0.0290 (9) | 0.0308 (9) | −0.0004 (7) | 0.0081 (7) | 0.0002 (8) |
C4 | 0.0308 (8) | 0.0328 (10) | 0.0298 (8) | 0.0004 (7) | 0.0074 (7) | 0.0007 (7) |
C5 | 0.0380 (9) | 0.0378 (11) | 0.0364 (9) | 0.0029 (8) | 0.0048 (7) | −0.0012 (8) |
C6 | 0.0391 (9) | 0.0534 (13) | 0.0324 (9) | 0.0031 (9) | 0.0015 (7) | 0.0007 (9) |
C7 | 0.0452 (10) | 0.0426 (12) | 0.0414 (10) | 0.0091 (8) | 0.0048 (8) | 0.0102 (9) |
C8 | 0.0447 (10) | 0.0316 (10) | 0.0443 (10) | 0.0047 (8) | 0.0087 (8) | 0.0061 (8) |
C9 | 0.0329 (8) | 0.0339 (10) | 0.0303 (8) | −0.0012 (7) | 0.0071 (7) | 0.0024 (8) |
C10 | 0.0420 (9) | 0.0369 (10) | 0.0315 (9) | 0.0013 (8) | 0.0062 (7) | 0.0015 (8) |
C11 | 0.0627 (11) | 0.0378 (11) | 0.0434 (10) | −0.0064 (9) | −0.0041 (9) | −0.0031 (9) |
C12 | 0.0435 (10) | 0.0356 (11) | 0.0415 (10) | 0.0010 (8) | 0.0002 (8) | −0.0023 (9) |
C13 | 0.0752 (13) | 0.0351 (11) | 0.0554 (11) | −0.0019 (10) | −0.0045 (10) | 0.0005 (9) |
O1—C10 | 1.2164 (17) | C6—C7 | 1.394 (2) |
O2—C12 | 1.2128 (17) | C6—H6 | 0.94 |
N—C1 | 1.3137 (18) | C7—C8 | 1.361 (2) |
N—C9 | 1.3723 (17) | C7—H7 | 0.94 |
C1—C2 | 1.406 (2) | C8—C9 | 1.408 (2) |
C1—C10 | 1.505 (2) | C8—H8 | 0.94 |
C2—C3 | 1.3713 (19) | C10—C11 | 1.493 (2) |
C2—H2 | 0.94 | C11—H11A | 0.97 |
C3—C4 | 1.429 (2) | C11—H11B | 0.97 |
C3—C12 | 1.501 (2) | C11—H11C | 0.97 |
C4—C9 | 1.418 (2) | C12—C13 | 1.487 (2) |
C4—C5 | 1.4206 (19) | C13—H13A | 0.97 |
C5—C6 | 1.361 (2) | C13—H13B | 0.97 |
C5—H5 | 0.94 | C13—H13C | 0.97 |
C1—N—C9 | 117.46 (13) | C7—C8—H8 | 119.7 |
N—C1—C2 | 123.82 (13) | C9—C8—H8 | 119.7 |
N—C1—C10 | 116.53 (14) | N—C9—C8 | 116.95 (14) |
C2—C1—C10 | 119.60 (13) | N—C9—C4 | 122.92 (13) |
C3—C2—C1 | 120.21 (14) | C8—C9—C4 | 120.10 (13) |
C3—C2—H2 | 119.9 | O1—C10—C11 | 122.41 (14) |
C1—C2—H2 | 119.9 | O1—C10—C1 | 119.76 (15) |
C2—C3—C4 | 117.95 (14) | C11—C10—C1 | 117.82 (14) |
C2—C3—C12 | 118.99 (13) | C10—C11—H11A | 109.5 |
C4—C3—C12 | 122.99 (13) | C10—C11—H11B | 109.5 |
C9—C4—C5 | 117.24 (14) | H11A—C11—H11B | 109.5 |
C9—C4—C3 | 117.63 (13) | C10—C11—H11C | 109.5 |
C5—C4—C3 | 125.13 (15) | H11A—C11—H11C | 109.5 |
C6—C5—C4 | 121.02 (16) | H11B—C11—H11C | 109.5 |
C6—C5—H5 | 119.5 | O2—C12—C13 | 119.64 (16) |
C4—C5—H5 | 119.5 | O2—C12—C3 | 121.21 (15) |
C5—C6—C7 | 121.08 (15) | C13—C12—C3 | 119.10 (13) |
C5—C6—H6 | 119.5 | C12—C13—H13A | 109.5 |
C7—C6—H6 | 119.5 | C12—C13—H13B | 109.5 |
C8—C7—C6 | 119.87 (16) | H13A—C13—H13B | 109.5 |
C8—C7—H7 | 120.1 | C12—C13—H13C | 109.5 |
C6—C7—H7 | 120.1 | H13A—C13—H13C | 109.5 |
C7—C8—C9 | 120.63 (16) | H13B—C13—H13C | 109.5 |
C9—N—C1—C2 | 0.0 (2) | C1—N—C9—C4 | 0.2 (2) |
C9—N—C1—C10 | −177.46 (12) | C7—C8—C9—N | −178.39 (14) |
N—C1—C2—C3 | −0.6 (2) | C7—C8—C9—C4 | 0.0 (2) |
C10—C1—C2—C3 | 176.78 (13) | C5—C4—C9—N | −179.72 (12) |
C1—C2—C3—C4 | 0.9 (2) | C3—C4—C9—N | 0.1 (2) |
C1—C2—C3—C12 | −176.29 (14) | C5—C4—C9—C8 | 2.0 (2) |
C2—C3—C4—C9 | −0.7 (2) | C3—C4—C9—C8 | −178.20 (13) |
C12—C3—C4—C9 | 176.44 (13) | N—C1—C10—O1 | −178.24 (14) |
C2—C3—C4—C5 | 179.12 (13) | C2—C1—C10—O1 | 4.2 (2) |
C12—C3—C4—C5 | −3.8 (2) | N—C1—C10—C11 | 1.2 (2) |
C9—C4—C5—C6 | −2.3 (2) | C2—C1—C10—C11 | −176.43 (15) |
C3—C4—C5—C6 | 177.91 (15) | C2—C3—C12—O2 | 156.46 (15) |
C4—C5—C6—C7 | 0.6 (2) | C4—C3—C12—O2 | −20.6 (2) |
C5—C6—C7—C8 | 1.5 (3) | C2—C3—C12—C13 | −20.9 (2) |
C6—C7—C8—C9 | −1.7 (2) | C4—C3—C12—C13 | 162.01 (14) |
C1—N—C9—C8 | 178.57 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13A···O1i | 0.97 | 2.57 | 3.531 (2) | 173 |
C13—H13B···O2ii | 0.97 | 2.51 | 3.392 (2) | 151 |
Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) x−1/2, −y+1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C13H11NO2 |
Mr | 213.23 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 203 |
a, b, c (Å) | 7.5285 (6), 15.0366 (12), 9.7202 (7) |
β (°) | 105.704 (9) |
V (Å3) | 1059.28 (14) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.57 × 0.43 × 0.41 |
Data collection | |
Diffractometer | Oxford Diffraction Gemini R |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9975, 3533, 1078 |
Rint | 0.058 |
(sin θ/λ)max (Å−1) | 0.758 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.114, 0.75 |
No. of reflections | 3533 |
No. of parameters | 147 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.29, −0.20 |
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 |
C13—H13A···O1i | 0.97 | 2.57 | 3.531 (2) | 173 |
C13—H13B···O2ii | 0.97 | 2.51 | 3.392 (2) | 151 |
Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) x−1/2, −y+1/2, z−1/2. |
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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 (Fig. 1).
One acetyl group is coplanar with the quinoline ring system, with a N—C1—C10—O1 torsion angle of -178.24 (14) Å, while the second is slightly twisted out of the plane, with a C2—C3—C12—C13 torsion angle of -20.9 (2)°.
Intermolecular C—H···O hydrogen bonding interactions involving the H13A and H13B methyl hydrogen atoms and acetyl oxygen atoms O1 and O2 link the molecules into a ribbon (Fig. 2). In addition, the crystal structure is stabilized by π-π stacking interactions between the pyridine rings of the inversion-related molecules at (x, y, z) and (-x, -y, -z), with the ring centroids separated by 3.5246 (9) Å.