organic compounds
7-[(Morpholin-4-yl)(phenyl)methyl]quinolin-8-ol
aDepartment of Physics, Idhaya College for Women, Kumbakonam-1, India, bDepartment of Physics, Kunthavai Naachiar Govt. Arts College (W) (Autonomous), Thanjavur-7, India, cDepartment of Chemistry, Urumu Dhanalakshmi College, Tiruchirappalli-19, India, dFribourg Center for Nanomaterials, FriMat, University of Fribourg, Switzerland, and eDepartment of Chemistry, University of Fribourg, Switzerland
*Correspondence e-mail: vasuki.arasi@yahoo.com
In the title compound, C20H20N2O2, the quinoline ring system makes dihedral angles of 81.05 (4) and 61.16 (5)° with the mean planes of the benzene and morpholine rings, respectively; the mean planes of the latter two rings make a dihedral angle of 83.59 (4)°. In the crystal, pairs of O—H⋯N hydrogen bonds link neighbouring molecules related by a twofold rotation axis, generating R22(10) motifs.
Related literature
For the biological activity of quinoline derivatives, see: Thakur et al. (2010). For hydrogen-bond motifs, see: Bernstein et al. (1995). For puckering parameters, see: Cremer & Pople (1975).
Experimental
Crystal data
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Data collection: X-AREA (Stoe & Cie, 2002); cell X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: PLATON (Spek, 2009).
Supporting information
https://doi.org/10.1107/S1600536812049343/gk2537sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812049343/gk2537Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812049343/gk2537Isup3.cml
8-Hydroxyquinoline (14.5 g; 0.1 mol) was dissolved in 25 ml of acetone and placed in a 250 ml beaker with constant stirring at 305 K for 1/2 h, then benzaldehyde (10.6 g; 0.1 mol) followed by morpholine (8.71 g; 0.1 mol) was added and the mixture was stirred well. The reaction mixture was left for 48 h and the resulting precipitate was collected by filtration and washed with cold water to give pale brown solid (m.p. 338 K) was obtained (yield: 70%). Single crystals suitable for X-ray diffraction were obtained from ethanol.
H1A of the OH group was located in an electron difference map and refined freely. Remaining H atoms were positioned geomentrically and allowed to ride on their parent atoms, with C—H = 0.95–1.00 Å and Uiso(H) = 1.2 times Ueq(C).
Quinoline analogues have been reported to display promising biological activities such as antimicrobial, anti–inflammatoty, antileishmanial, antituberculosis, antimalarial, cytotoxicity and HIV–1 integrase inhibitors (Thakur et al., 2010). In continuation of our efforts to develop quinoline derivatives with a new structure–activity relationalship, herein, we report the synthesis and
of the title compound.In the title molecule (Fig.1), the benzene(C11—C16) and morpholine (N2/O2/C17—C20) rings make dihedral angles of 81.05 (4)° and 61.16 (5)° with the quinoline ring system, respectively. The dihedral angle between the benzene and morpholine rings is 83.59 (4)°. The title molecule is chiral with a chiral centre at C10. The morpholine ring adopts an almost perfect normal chair conformation having total puckering amplitude, QT of 0.5876 (15) Å, θ = 3.34 (14)° and φ = 176 (3)° (Cremer & Pople, 1975). The sum of the bond angles around N2 [329.13 (32)°] indicates a pyramidal geometry. The N2 atom deviates by 0.2613 (10) Å from the least–squares plane passing through atoms C17—C20.
In the crystal packing (Fig. 2), intermolecular O—H···N hydrogen bonds (Table 1) link the neighbouring molecules and generate an R22(10) motif (Bernstein et al., 1995).
At x=0.0, y= 0.0, z= 0.321 the crystal contains small void with the solvent accessible volume of 33 Å3.
For the biological activity of quinoline derivatives, see: Thakur et al. (2010). For hydrogen-bond motifs, see: Bernstein et al. (1995). For puckering parameters, see: Cremer & Pople (1975).
Data collection: X-AREA (Stoe & Cie, 2002); cell
X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: PLATON (Spek, 2009).C20H20N2O2 | F(000) = 1360 |
Mr = 320.38 | Dx = 1.251 Mg m−3 |
Orthorhombic, Aba2 | Cu Kα radiation, λ = 1.54186 Å |
Hall symbol: A 2 -2ac | Cell parameters from 29594 reflections |
a = 13.1537 (6) Å | θ = 3.4–67.3° |
b = 31.0875 (13) Å | µ = 0.65 mm−1 |
c = 8.3175 (3) Å | T = 200 K |
V = 3401.2 (2) Å3 | Block, brown |
Z = 8 | 0.60 × 0.32 × 0.17 mm |
Stoe IPDS 2 diffractometer | 2776 independent reflections |
Radiation source: fine-focus sealed tube | 2696 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.074 |
Detector resolution: 6.67 pixels mm-1 | θmax = 64.9°, θmin = 4.4° |
rotation method scans | h = −15→15 |
Absorption correction: integration (X-SHAPE: Stoe & Cie, 2002) | k = −34→34 |
Tmin = 0.696, Tmax = 0.898 | l = −9→9 |
12678 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.028 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.074 | w = 1/[σ2(Fo2) + (0.0315P)2 + 1.0277P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
2776 reflections | Δρmax = 0.16 e Å−3 |
218 parameters | Δρmin = −0.14 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 1273 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.05 (18) |
C20H20N2O2 | V = 3401.2 (2) Å3 |
Mr = 320.38 | Z = 8 |
Orthorhombic, Aba2 | Cu Kα radiation |
a = 13.1537 (6) Å | µ = 0.65 mm−1 |
b = 31.0875 (13) Å | T = 200 K |
c = 8.3175 (3) Å | 0.60 × 0.32 × 0.17 mm |
Stoe IPDS 2 diffractometer | 2776 independent reflections |
Absorption correction: integration (X-SHAPE: Stoe & Cie, 2002) | 2696 reflections with I > 2σ(I) |
Tmin = 0.696, Tmax = 0.898 | Rint = 0.074 |
12678 measured reflections |
R[F2 > 2σ(F2)] = 0.028 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.074 | Δρmax = 0.16 e Å−3 |
S = 1.06 | Δρmin = −0.14 e Å−3 |
2776 reflections | Absolute structure: Flack (1983), 1273 Friedel pairs |
218 parameters | Absolute structure parameter: −0.05 (18) |
1 restraint |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 | ||
H1A | 0.0489 (15) | 0.4676 (7) | 0.270 (3) | 0.055 (6)* | |
O1 | 0.05418 (7) | 0.44234 (3) | 0.30675 (14) | 0.0289 (2) | |
O2 | 0.17007 (9) | 0.23324 (3) | 0.25602 (15) | 0.0419 (3) | |
N1 | −0.11876 (8) | 0.47965 (3) | 0.18343 (15) | 0.0273 (3) | |
N2 | 0.07402 (8) | 0.30989 (3) | 0.37537 (14) | 0.0238 (2) | |
C1 | −0.20163 (10) | 0.49659 (4) | 0.1212 (2) | 0.0329 (3) | |
H1 | −0.2005 | 0.5263 | 0.0942 | 0.040* | |
C2 | −0.29128 (11) | 0.47365 (5) | 0.0923 (2) | 0.0371 (4) | |
H2 | −0.3488 | 0.4875 | 0.0464 | 0.045* | |
C3 | −0.29459 (11) | 0.43097 (5) | 0.1313 (2) | 0.0357 (3) | |
H3 | −0.3549 | 0.4148 | 0.1137 | 0.043* | |
C4 | −0.20791 (10) | 0.41094 (4) | 0.19806 (18) | 0.0272 (3) | |
C5 | −0.20411 (10) | 0.36710 (4) | 0.24473 (19) | 0.0319 (3) | |
H5 | −0.2622 | 0.3493 | 0.2311 | 0.038* | |
C6 | −0.11734 (10) | 0.35043 (4) | 0.30904 (18) | 0.0285 (3) | |
H6 | −0.1166 | 0.3211 | 0.3412 | 0.034* | |
C7 | −0.02833 (10) | 0.37537 (4) | 0.32952 (16) | 0.0225 (3) | |
C8 | −0.03074 (9) | 0.41828 (4) | 0.28592 (16) | 0.0214 (3) | |
C9 | −0.12057 (10) | 0.43685 (4) | 0.22082 (16) | 0.0230 (3) | |
C10 | 0.06862 (9) | 0.35690 (4) | 0.40229 (17) | 0.0224 (3) | |
H10 | 0.1280 | 0.3705 | 0.3472 | 0.027* | |
C11 | 0.07299 (9) | 0.36868 (4) | 0.57945 (16) | 0.0234 (3) | |
C12 | −0.00026 (10) | 0.35446 (4) | 0.68860 (19) | 0.0284 (3) | |
H12 | −0.0524 | 0.3355 | 0.6533 | 0.034* | |
C13 | 0.00197 (11) | 0.36756 (5) | 0.8477 (2) | 0.0364 (3) | |
H13 | −0.0482 | 0.3575 | 0.9206 | 0.044* | |
C14 | 0.07713 (9) | 0.39534 (4) | 0.90078 (15) | 0.0433 (4) | |
H14 | 0.0784 | 0.4046 | 1.0096 | 0.052* | |
C15 | 0.15029 (9) | 0.40941 (4) | 0.79385 (15) | 0.0460 (4) | |
H15 | 0.2025 | 0.4282 | 0.8296 | 0.055* | |
C16 | 0.14802 (12) | 0.39625 (5) | 0.6350 (2) | 0.0356 (4) | |
H16 | 0.1987 | 0.4063 | 0.5628 | 0.043* | |
C17 | 0.08639 (12) | 0.30128 (5) | 0.20274 (19) | 0.0326 (3) | |
H17A | 0.1505 | 0.3143 | 0.1640 | 0.039* | |
H17B | 0.0294 | 0.3143 | 0.1423 | 0.039* | |
C18 | 0.08844 (13) | 0.25335 (5) | 0.1737 (2) | 0.0419 (4) | |
H18A | 0.0234 | 0.2406 | 0.2103 | 0.050* | |
H18B | 0.0951 | 0.2478 | 0.0570 | 0.050* | |
C19 | 0.16175 (12) | 0.24197 (5) | 0.4233 (2) | 0.0374 (4) | |
H19A | 0.2197 | 0.2286 | 0.4803 | 0.045* | |
H19B | 0.0984 | 0.2289 | 0.4650 | 0.045* | |
C20 | 0.16062 (10) | 0.28999 (5) | 0.45816 (19) | 0.0305 (3) | |
H20A | 0.1549 | 0.2949 | 0.5754 | 0.037* | |
H20B | 0.2248 | 0.3032 | 0.4205 | 0.037* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0244 (4) | 0.0184 (5) | 0.0438 (6) | −0.0052 (3) | −0.0056 (4) | 0.0051 (4) |
O2 | 0.0467 (6) | 0.0311 (5) | 0.0478 (7) | 0.0138 (5) | −0.0028 (5) | −0.0093 (5) |
N1 | 0.0302 (6) | 0.0186 (5) | 0.0330 (6) | 0.0001 (4) | −0.0026 (5) | 0.0014 (5) |
N2 | 0.0266 (5) | 0.0184 (5) | 0.0264 (6) | 0.0027 (4) | −0.0018 (4) | −0.0012 (4) |
C1 | 0.0367 (7) | 0.0213 (7) | 0.0408 (8) | 0.0016 (6) | −0.0069 (7) | 0.0043 (6) |
C2 | 0.0339 (7) | 0.0315 (8) | 0.0461 (10) | 0.0042 (6) | −0.0145 (7) | 0.0012 (7) |
C3 | 0.0294 (7) | 0.0309 (7) | 0.0467 (9) | −0.0037 (6) | −0.0110 (6) | −0.0011 (7) |
C4 | 0.0261 (6) | 0.0235 (6) | 0.0318 (7) | −0.0024 (5) | −0.0038 (6) | −0.0012 (6) |
C5 | 0.0251 (6) | 0.0236 (7) | 0.0471 (10) | −0.0068 (5) | −0.0065 (6) | 0.0010 (6) |
C6 | 0.0288 (7) | 0.0189 (6) | 0.0377 (8) | −0.0030 (5) | −0.0013 (6) | 0.0038 (6) |
C7 | 0.0246 (6) | 0.0198 (6) | 0.0230 (6) | −0.0003 (5) | 0.0012 (5) | −0.0006 (5) |
C8 | 0.0230 (6) | 0.0178 (6) | 0.0235 (6) | −0.0032 (5) | 0.0012 (5) | −0.0014 (5) |
C9 | 0.0265 (6) | 0.0178 (6) | 0.0246 (7) | −0.0013 (5) | 0.0000 (5) | −0.0022 (5) |
C10 | 0.0224 (6) | 0.0180 (6) | 0.0269 (7) | −0.0010 (5) | 0.0019 (5) | 0.0000 (5) |
C11 | 0.0248 (6) | 0.0188 (6) | 0.0265 (7) | 0.0028 (5) | −0.0005 (5) | 0.0016 (5) |
C12 | 0.0264 (6) | 0.0256 (7) | 0.0333 (7) | 0.0013 (5) | 0.0014 (6) | 0.0029 (6) |
C13 | 0.0398 (8) | 0.0382 (8) | 0.0313 (8) | 0.0021 (6) | 0.0080 (7) | 0.0062 (7) |
C14 | 0.0573 (10) | 0.0468 (9) | 0.0258 (8) | −0.0023 (8) | 0.0003 (7) | −0.0043 (7) |
C15 | 0.0552 (9) | 0.0495 (10) | 0.0331 (9) | −0.0194 (8) | −0.0039 (8) | −0.0075 (8) |
C16 | 0.0390 (8) | 0.0402 (8) | 0.0276 (8) | −0.0141 (6) | 0.0005 (6) | −0.0010 (7) |
C17 | 0.0399 (7) | 0.0281 (7) | 0.0298 (8) | 0.0045 (6) | −0.0026 (6) | −0.0033 (6) |
C18 | 0.0494 (9) | 0.0336 (8) | 0.0428 (9) | 0.0096 (7) | −0.0097 (8) | −0.0104 (7) |
C19 | 0.0392 (8) | 0.0282 (7) | 0.0449 (9) | 0.0111 (6) | −0.0039 (7) | 0.0006 (7) |
C20 | 0.0278 (7) | 0.0290 (7) | 0.0346 (8) | 0.0066 (6) | −0.0040 (6) | −0.0004 (6) |
O1—C8 | 1.3554 (15) | C10—C11 | 1.5195 (18) |
O1—H1A | 0.85 (2) | C10—H10 | 1.0000 |
O2—C18 | 1.4185 (19) | C11—C16 | 1.386 (2) |
O2—C19 | 1.422 (2) | C11—C12 | 1.3957 (19) |
N1—C1 | 1.3165 (18) | C12—C13 | 1.385 (2) |
N1—C9 | 1.3668 (17) | C12—H12 | 0.9500 |
N2—C20 | 1.4680 (17) | C13—C14 | 1.385 (2) |
N2—C17 | 1.4696 (19) | C13—H13 | 0.9500 |
N2—C10 | 1.4802 (16) | C14—C15 | 1.3815 |
C1—C2 | 1.399 (2) | C14—H14 | 0.9500 |
C1—H1 | 0.9500 | C15—C16 | 1.383 (2) |
C2—C3 | 1.367 (2) | C15—H15 | 0.9500 |
C2—H2 | 0.9500 | C16—H16 | 0.9500 |
C3—C4 | 1.4125 (19) | C17—C18 | 1.510 (2) |
C3—H3 | 0.9500 | C17—H17A | 0.9900 |
C4—C9 | 1.4157 (18) | C17—H17B | 0.9900 |
C4—C5 | 1.418 (2) | C18—H18A | 0.9900 |
C5—C6 | 1.363 (2) | C18—H18B | 0.9900 |
C5—H5 | 0.9500 | C19—C20 | 1.521 (2) |
C6—C7 | 1.4145 (18) | C19—H19A | 0.9900 |
C6—H6 | 0.9500 | C19—H19B | 0.9900 |
C7—C8 | 1.3829 (17) | C20—H20A | 0.9900 |
C7—C10 | 1.5238 (18) | C20—H20B | 0.9900 |
C8—C9 | 1.4221 (18) | ||
C8—O1—H1A | 113.6 (14) | C12—C11—C10 | 121.89 (12) |
C18—O2—C19 | 109.25 (12) | C13—C12—C11 | 120.92 (13) |
C1—N1—C9 | 117.67 (11) | C13—C12—H12 | 119.5 |
C20—N2—C17 | 107.19 (11) | C11—C12—H12 | 119.5 |
C20—N2—C10 | 112.49 (10) | C12—C13—C14 | 120.22 (13) |
C17—N2—C10 | 109.45 (11) | C12—C13—H13 | 119.9 |
N1—C1—C2 | 124.18 (12) | C14—C13—H13 | 119.9 |
N1—C1—H1 | 117.9 | C15—C14—C13 | 119.30 (8) |
C2—C1—H1 | 117.9 | C15—C14—H14 | 120.4 |
C3—C2—C1 | 118.74 (13) | C13—C14—H14 | 120.4 |
C3—C2—H2 | 120.6 | C14—C15—C16 | 120.40 (8) |
C1—C2—H2 | 120.6 | C14—C15—H15 | 119.8 |
C2—C3—C4 | 119.70 (13) | C16—C15—H15 | 119.8 |
C2—C3—H3 | 120.1 | C15—C16—C11 | 121.10 (13) |
C4—C3—H3 | 120.1 | C15—C16—H16 | 119.4 |
C3—C4—C9 | 117.19 (12) | C11—C16—H16 | 119.4 |
C3—C4—C5 | 124.03 (12) | N2—C17—C18 | 109.75 (13) |
C9—C4—C5 | 118.78 (12) | N2—C17—H17A | 109.7 |
C6—C5—C4 | 120.16 (12) | C18—C17—H17A | 109.7 |
C6—C5—H5 | 119.9 | N2—C17—H17B | 109.7 |
C4—C5—H5 | 119.9 | C18—C17—H17B | 109.7 |
C5—C6—C7 | 122.15 (12) | H17A—C17—H17B | 108.2 |
C5—C6—H6 | 118.9 | O2—C18—C17 | 111.81 (13) |
C7—C6—H6 | 118.9 | O2—C18—H18A | 109.3 |
C8—C7—C6 | 118.56 (11) | C17—C18—H18A | 109.3 |
C8—C7—C10 | 119.13 (11) | O2—C18—H18B | 109.3 |
C6—C7—C10 | 122.28 (11) | C17—C18—H18B | 109.3 |
O1—C8—C7 | 118.68 (11) | H18A—C18—H18B | 107.9 |
O1—C8—C9 | 120.63 (11) | O2—C19—C20 | 112.01 (13) |
C7—C8—C9 | 120.69 (11) | O2—C19—H19A | 109.2 |
N1—C9—C4 | 122.51 (12) | C20—C19—H19A | 109.2 |
N1—C9—C8 | 117.86 (11) | O2—C19—H19B | 109.2 |
C4—C9—C8 | 119.63 (11) | C20—C19—H19B | 109.2 |
N2—C10—C11 | 112.51 (11) | H19A—C19—H19B | 107.9 |
N2—C10—C7 | 110.61 (10) | N2—C20—C19 | 109.38 (12) |
C11—C10—C7 | 109.03 (10) | N2—C20—H20A | 109.8 |
N2—C10—H10 | 108.2 | C19—C20—H20A | 109.8 |
C11—C10—H10 | 108.2 | N2—C20—H20B | 109.8 |
C7—C10—H10 | 108.2 | C19—C20—H20B | 109.8 |
C16—C11—C12 | 118.06 (13) | H20A—C20—H20B | 108.2 |
C16—C11—C10 | 119.95 (12) | ||
C9—N1—C1—C2 | 0.5 (2) | C20—N2—C10—C7 | −173.89 (11) |
N1—C1—C2—C3 | 0.4 (3) | C17—N2—C10—C7 | 67.06 (14) |
C1—C2—C3—C4 | −0.6 (3) | C8—C7—C10—N2 | −155.26 (12) |
C2—C3—C4—C9 | −0.1 (2) | C6—C7—C10—N2 | 26.60 (17) |
C2—C3—C4—C5 | 179.03 (16) | C8—C7—C10—C11 | 80.52 (15) |
C3—C4—C5—C6 | −179.64 (15) | C6—C7—C10—C11 | −97.63 (14) |
C9—C4—C5—C6 | −0.5 (2) | N2—C10—C11—C16 | 122.96 (13) |
C4—C5—C6—C7 | −1.0 (2) | C7—C10—C11—C16 | −113.94 (14) |
C5—C6—C7—C8 | 1.5 (2) | N2—C10—C11—C12 | −60.73 (15) |
C5—C6—C7—C10 | 179.64 (13) | C7—C10—C11—C12 | 62.37 (15) |
C6—C7—C8—O1 | 179.42 (12) | C16—C11—C12—C13 | 0.05 (19) |
C10—C7—C8—O1 | 1.21 (19) | C10—C11—C12—C13 | −176.33 (13) |
C6—C7—C8—C9 | −0.45 (19) | C11—C12—C13—C14 | 0.4 (2) |
C10—C7—C8—C9 | −178.66 (12) | C12—C13—C14—C15 | −0.71 (17) |
C1—N1—C9—C4 | −1.3 (2) | C13—C14—C15—C16 | 0.63 (11) |
C1—N1—C9—C8 | 179.12 (14) | C14—C15—C16—C11 | −0.20 (18) |
C3—C4—C9—N1 | 1.1 (2) | C12—C11—C16—C15 | −0.1 (2) |
C5—C4—C9—N1 | −178.08 (14) | C10—C11—C16—C15 | 176.31 (13) |
C3—C4—C9—C8 | −179.32 (14) | C20—N2—C17—C18 | 59.61 (15) |
C5—C4—C9—C8 | 1.5 (2) | C10—N2—C17—C18 | −178.12 (11) |
O1—C8—C9—N1 | −1.29 (19) | C19—O2—C18—C17 | 57.69 (18) |
C7—C8—C9—N1 | 178.58 (13) | N2—C17—C18—O2 | −60.32 (18) |
O1—C8—C9—C4 | 179.12 (12) | C18—O2—C19—C20 | −57.41 (16) |
C7—C8—C9—C4 | −1.0 (2) | C17—N2—C20—C19 | −58.99 (15) |
C20—N2—C10—C11 | −51.69 (15) | C10—N2—C20—C19 | −179.34 (12) |
C17—N2—C10—C11 | −170.73 (11) | O2—C19—C20—N2 | 59.55 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···N1i | 0.85 (2) | 2.01 (2) | 2.7668 (14) | 148 (18) |
Symmetry code: (i) −x, −y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C20H20N2O2 |
Mr | 320.38 |
Crystal system, space group | Orthorhombic, Aba2 |
Temperature (K) | 200 |
a, b, c (Å) | 13.1537 (6), 31.0875 (13), 8.3175 (3) |
V (Å3) | 3401.2 (2) |
Z | 8 |
Radiation type | Cu Kα |
µ (mm−1) | 0.65 |
Crystal size (mm) | 0.60 × 0.32 × 0.17 |
Data collection | |
Diffractometer | Stoe IPDS 2 |
Absorption correction | Integration (X-SHAPE: Stoe & Cie, 2002) |
Tmin, Tmax | 0.696, 0.898 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12678, 2776, 2696 |
Rint | 0.074 |
(sin θ/λ)max (Å−1) | 0.588 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.028, 0.074, 1.06 |
No. of reflections | 2776 |
No. of parameters | 218 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.16, −0.14 |
Absolute structure | Flack (1983), 1273 Friedel pairs |
Absolute structure parameter | −0.05 (18) |
Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012) and Mercury (Macrae et al., 2008), PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···N1i | 0.85 (2) | 2.01 (2) | 2.7668 (14) | 148 (18) |
Symmetry code: (i) −x, −y+1, z. |
Acknowledgements
The authors thank the Fribourg Center for Nanomaterials, FriMat, University of Fribourg, Switzerland, 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.
Quinoline analogues have been reported to display promising biological activities such as antimicrobial, anti–inflammatoty, antileishmanial, antituberculosis, antimalarial, cytotoxicity and HIV–1 integrase inhibitors (Thakur et al., 2010). In continuation of our efforts to develop quinoline derivatives with a new structure–activity relationalship, herein, we report the synthesis and structure determination of the title compound.
In the title molecule (Fig.1), the benzene(C11—C16) and morpholine (N2/O2/C17—C20) rings make dihedral angles of 81.05 (4)° and 61.16 (5)° with the quinoline ring system, respectively. The dihedral angle between the benzene and morpholine rings is 83.59 (4)°. The title molecule is chiral with a chiral centre at C10. The morpholine ring adopts an almost perfect normal chair conformation having total puckering amplitude, QT of 0.5876 (15) Å, θ = 3.34 (14)° and φ = 176 (3)° (Cremer & Pople, 1975). The sum of the bond angles around N2 [329.13 (32)°] indicates a pyramidal geometry. The N2 atom deviates by 0.2613 (10) Å from the least–squares plane passing through atoms C17—C20.
In the crystal packing (Fig. 2), intermolecular O—H···N hydrogen bonds (Table 1) link the neighbouring molecules and generate an R22(10) motif (Bernstein et al., 1995).
At x=0.0, y= 0.0, z= 0.321 the crystal contains small void with the solvent accessible volume of 33 Å3.