organic compounds
Ethyl 2-methyl-4-phenylquinoline-3-carboxylate
aDepartment of Chemistry, Islamic Azad University, Dorood Branch, Dorood 688173551, Iran
*Correspondence e-mail: a_bazgir@yahoo.com
In the molecule of the title compound, C19H17NO2, the quinoline ring system is planar [maximum deviation 0.021 (3) Å] and oriented with respect to the phenyl ring at a dihedral angle of 80.44 (4)°. Intramolecular C—H⋯O interactions result in the formation of five- and six-membered rings having planar and envelope conformations, respectively. In the intermolecular C—H⋯O interactions link the molecules into centrosymmetric dimers forming R22(12) ring motifs. π–π contacts between the rings of the quinoline system [centroid-to-centroid distance = 3.812 (1) Å] may further stabilize the structure. Two weak C—H⋯π interactions are also found.
Related literature
For general background, see: Doube et al. (1998). For ring-motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987).
Experimental
Crystal data
|
Data collection
|
Refinement
|
Data collection: SMART (Bruker, 1998); cell SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON.
Supporting information
10.1107/S1600536809018625/hk2681sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809018625/hk2681Isup2.hkl
For the preparation of the title compound, a mixture of ethyl acetoacetate (0.13 g, 1 mmol), (2-aminophenyl)(phenyl)methanone (0.20 g, 1 mmol) and p-toluene sulfonic acid (0.1 g, 5.8 mmol) in water (5 ml) was stirred at reflux for 4 h. After completion of reaction (monitored by TLC) the reaction mixture was filtered and the precipitate washed with water (15 ml) and then recrystallized from EtOH/water (1:2) to afford the pure product (yield; 75%, 0.218 g).
H atoms were positioned geometrically, with C—H = 0.93, 0.97 and 0.96 Å for aromatic, methylene and methyl H, respectively, and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C).
Data collection: SMART (Bruker, 1998); cell
SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Hydrogen bonds are shown as dotted lines. | |
Fig. 2. A partial packing diagram of the title compound. Hydrogen bonds are shown as dashed lines. |
C19H17NO2 | Z = 2 |
Mr = 291.34 | F(000) = 308 |
Triclinic, P1 | Dx = 1.271 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.0282 (10) Å | Cell parameters from 1548 reflections |
b = 9.362 (1) Å | θ = 2.4–29.2° |
c = 10.7258 (10) Å | µ = 0.08 mm−1 |
α = 69.765 (8)° | T = 120 K |
β = 66.733 (8)° | Block, colourless |
γ = 70.605 (8)° | 0.35 × 0.32 × 0.25 mm |
V = 761.08 (15) Å3 |
Bruker SMART CCD area-detector diffractometer | Rint = 0.044 |
ϕ and ω scans | θmax = 29.2°, θmin = 2.4° |
8164 measured reflections | h = −12→12 |
3995 independent reflections | k = −12→12 |
3410 reflections with I > 2σ(I) | l = −13→14 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.065 | w = 1/[σ2(Fo2) + (0.0955P)2 + 0.1587P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.194 | (Δ/σ)max = 0.01 |
S = 1.09 | Δρmax = 0.33 e Å−3 |
3995 reflections | Δρmin = −0.35 e Å−3 |
199 parameters |
C19H17NO2 | γ = 70.605 (8)° |
Mr = 291.34 | V = 761.08 (15) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.0282 (10) Å | Mo Kα radiation |
b = 9.362 (1) Å | µ = 0.08 mm−1 |
c = 10.7258 (10) Å | T = 120 K |
α = 69.765 (8)° | 0.35 × 0.32 × 0.25 mm |
β = 66.733 (8)° |
Bruker SMART CCD area-detector diffractometer | 3410 reflections with I > 2σ(I) |
8164 measured reflections | Rint = 0.044 |
3995 independent reflections |
R[F2 > 2σ(F2)] = 0.065 | 0 restraints |
wR(F2) = 0.194 | H-atom parameters constrained |
S = 1.09 | Δρmax = 0.33 e Å−3 |
3995 reflections | Δρmin = −0.35 e Å−3 |
199 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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.6903 (3) | −0.70878 (17) | 0.11893 (14) | 0.0879 (5) | |
O2 | 0.6965 (2) | −0.95151 (14) | 0.24871 (13) | 0.0696 (4) | |
N1 | 0.44256 (15) | −0.71135 (15) | 0.57975 (13) | 0.0470 (3) | |
C1 | 0.56342 (18) | −0.68228 (16) | 0.60840 (15) | 0.0438 (3) | |
C2 | 0.5192 (2) | −0.6418 (2) | 0.73600 (17) | 0.0551 (4) | |
H2 | 0.4104 | −0.6328 | 0.7953 | 0.066* | |
C3 | 0.6347 (3) | −0.6159 (2) | 0.77284 (19) | 0.0622 (5) | |
H3 | 0.6046 | −0.5907 | 0.8575 | 0.075* | |
C4 | 0.7988 (2) | −0.6273 (2) | 0.6834 (2) | 0.0615 (4) | |
H4 | 0.8767 | −0.6096 | 0.7094 | 0.074* | |
C5 | 0.8456 (2) | −0.66413 (19) | 0.55808 (18) | 0.0523 (4) | |
H5 | 0.9545 | −0.6702 | 0.4994 | 0.063* | |
C6 | 0.72854 (17) | −0.69295 (15) | 0.51769 (15) | 0.0420 (3) | |
C7 | 0.76870 (17) | −0.73393 (15) | 0.38991 (14) | 0.0402 (3) | |
C8 | 0.94211 (17) | −0.75008 (16) | 0.29187 (15) | 0.0423 (3) | |
C9 | 1.0023 (2) | −0.61966 (19) | 0.20110 (18) | 0.0546 (4) | |
H9 | 0.9326 | −0.5206 | 0.1985 | 0.066* | |
C10 | 1.1658 (2) | −0.6361 (2) | 0.11427 (19) | 0.0619 (4) | |
H10 | 1.2049 | −0.5483 | 0.0535 | 0.074* | |
C11 | 1.2697 (2) | −0.7819 (2) | 0.11829 (18) | 0.0612 (5) | |
H11 | 1.3796 | −0.7925 | 0.0614 | 0.073* | |
C12 | 1.2116 (2) | −0.9125 (2) | 0.20633 (19) | 0.0622 (4) | |
H12 | 1.2818 | −1.0112 | 0.2081 | 0.075* | |
C13 | 1.0480 (2) | −0.89658 (18) | 0.29248 (17) | 0.0526 (4) | |
H13 | 1.009 | −0.9851 | 0.3512 | 0.063* | |
C14 | 0.64476 (17) | −0.76184 (16) | 0.36344 (14) | 0.0410 (3) | |
C15 | 0.67936 (18) | −0.80112 (17) | 0.22859 (15) | 0.0451 (3) | |
C16 | 0.7336 (3) | −1.0130 (2) | 0.12943 (19) | 0.0640 (5) | |
H16A | 0.7594 | −0.9331 | 0.0428 | 0.077* | |
H16B | 0.6389 | −1.0461 | 0.1365 | 0.077* | |
C17 | 0.8780 (3) | −1.1482 (3) | 0.1307 (2) | 0.0694 (5) | |
H17A | 0.8511 | −1.2265 | 0.2168 | 0.083* | |
H17B | 0.9711 | −1.114 | 0.1231 | 0.083* | |
H17C | 0.905 | −1.1913 | 0.0532 | 0.083* | |
C18 | 0.48148 (18) | −0.75086 (17) | 0.46289 (15) | 0.0441 (3) | |
C19 | 0.3470 (2) | −0.7867 (2) | 0.43737 (19) | 0.0577 (4) | |
H19A | 0.2567 | −0.6965 | 0.4356 | 0.069* | |
H19B | 0.3086 | −0.8727 | 0.511 | 0.069* | |
H19C | 0.3897 | −0.8138 | 0.3491 | 0.069* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.1583 (17) | 0.0598 (8) | 0.0463 (7) | −0.0329 (9) | −0.0344 (9) | −0.0036 (6) |
O2 | 0.1184 (12) | 0.0481 (6) | 0.0487 (6) | −0.0242 (7) | −0.0284 (7) | −0.0121 (5) |
N1 | 0.0443 (6) | 0.0499 (7) | 0.0454 (6) | −0.0124 (5) | −0.0135 (5) | −0.0091 (5) |
C1 | 0.0471 (7) | 0.0398 (6) | 0.0437 (7) | −0.0072 (5) | −0.0161 (6) | −0.0096 (5) |
C2 | 0.0607 (9) | 0.0556 (9) | 0.0460 (8) | −0.0086 (7) | −0.0143 (7) | −0.0166 (6) |
C3 | 0.0786 (12) | 0.0623 (10) | 0.0558 (9) | −0.0085 (8) | −0.0288 (9) | −0.0248 (8) |
C4 | 0.0684 (11) | 0.0631 (10) | 0.0709 (11) | −0.0092 (8) | −0.0375 (9) | −0.0251 (8) |
C5 | 0.0494 (8) | 0.0540 (8) | 0.0629 (9) | −0.0071 (6) | −0.0261 (7) | −0.0203 (7) |
C6 | 0.0437 (7) | 0.0376 (6) | 0.0472 (7) | −0.0052 (5) | −0.0191 (6) | −0.0117 (5) |
C7 | 0.0408 (6) | 0.0364 (6) | 0.0433 (7) | −0.0082 (5) | −0.0146 (5) | −0.0087 (5) |
C8 | 0.0411 (6) | 0.0440 (7) | 0.0442 (7) | −0.0097 (5) | −0.0151 (5) | −0.0119 (5) |
C9 | 0.0563 (9) | 0.0464 (8) | 0.0594 (9) | −0.0154 (6) | −0.0170 (7) | −0.0090 (6) |
C10 | 0.0627 (10) | 0.0744 (11) | 0.0509 (9) | −0.0347 (9) | −0.0119 (7) | −0.0071 (8) |
C11 | 0.0454 (8) | 0.0894 (13) | 0.0472 (8) | −0.0166 (8) | −0.0103 (6) | −0.0190 (8) |
C12 | 0.0497 (9) | 0.0676 (10) | 0.0589 (9) | 0.0023 (7) | −0.0163 (7) | −0.0192 (8) |
C13 | 0.0499 (8) | 0.0455 (7) | 0.0544 (8) | −0.0070 (6) | −0.0147 (6) | −0.0086 (6) |
C14 | 0.0442 (7) | 0.0394 (6) | 0.0405 (6) | −0.0110 (5) | −0.0151 (5) | −0.0075 (5) |
C15 | 0.0476 (7) | 0.0471 (7) | 0.0435 (7) | −0.0142 (6) | −0.0163 (6) | −0.0089 (5) |
C16 | 0.0854 (13) | 0.0621 (10) | 0.0558 (9) | −0.0166 (9) | −0.0259 (9) | −0.0238 (8) |
C17 | 0.0650 (11) | 0.0801 (13) | 0.0642 (11) | −0.0162 (9) | −0.0143 (9) | −0.0266 (9) |
C18 | 0.0433 (7) | 0.0452 (7) | 0.0439 (7) | −0.0124 (5) | −0.0162 (5) | −0.0060 (5) |
C19 | 0.0497 (8) | 0.0728 (11) | 0.0576 (9) | −0.0221 (8) | −0.0213 (7) | −0.0115 (8) |
C1—N1 | 1.3708 (19) | C11—H11 | 0.93 |
C1—C6 | 1.415 (2) | C12—C13 | 1.388 (2) |
C1—C2 | 1.415 (2) | C12—H12 | 0.93 |
C2—C3 | 1.365 (3) | C13—H13 | 0.93 |
C2—H2 | 0.93 | C14—C18 | 1.433 (2) |
C3—C4 | 1.403 (3) | C14—C15 | 1.5031 (19) |
C3—H3 | 0.93 | C15—O1 | 1.1841 (19) |
C4—C5 | 1.371 (2) | C15—O2 | 1.3132 (19) |
C4—H4 | 0.93 | C16—O2 | 1.457 (2) |
C5—C6 | 1.417 (2) | C16—C17 | 1.485 (3) |
C5—H5 | 0.93 | C16—H16A | 0.97 |
C6—C7 | 1.4268 (19) | C16—H16B | 0.97 |
C7—C14 | 1.3775 (19) | C17—H17A | 0.96 |
C7—C8 | 1.4939 (19) | C17—H17B | 0.96 |
C8—C13 | 1.387 (2) | C17—H17C | 0.96 |
C8—C9 | 1.391 (2) | C18—N1 | 1.311 (2) |
C9—C10 | 1.390 (2) | C18—C19 | 1.503 (2) |
C9—H9 | 0.93 | C19—H19A | 0.96 |
C10—C11 | 1.373 (3) | C19—H19B | 0.96 |
C10—H10 | 0.93 | C19—H19C | 0.96 |
C11—C12 | 1.378 (3) | ||
N1—C1—C6 | 123.08 (13) | C11—C12—H12 | 120 |
N1—C1—C2 | 117.62 (14) | C13—C12—H12 | 120 |
C6—C1—C2 | 119.30 (14) | C8—C13—C12 | 120.70 (15) |
C3—C2—C1 | 120.59 (16) | C8—C13—H13 | 119.7 |
C3—C2—H2 | 119.7 | C12—C13—H13 | 119.7 |
C1—C2—H2 | 119.7 | C7—C14—C18 | 120.33 (13) |
C2—C3—C4 | 120.20 (16) | C7—C14—C15 | 120.08 (12) |
C2—C3—H3 | 119.9 | C18—C14—C15 | 119.58 (12) |
C4—C3—H3 | 119.9 | O1—C15—O2 | 124.63 (15) |
C5—C4—C3 | 120.81 (15) | O1—C15—C14 | 124.46 (14) |
C5—C4—H4 | 119.6 | O2—C15—C14 | 110.91 (12) |
C3—C4—H4 | 119.6 | O2—C16—C17 | 107.69 (15) |
C4—C5—C6 | 120.21 (16) | O2—C16—H16A | 110.2 |
C4—C5—H5 | 119.9 | C17—C16—H16A | 110.2 |
C6—C5—H5 | 119.9 | O2—C16—H16B | 110.2 |
C1—C6—C5 | 118.89 (13) | C17—C16—H16B | 110.2 |
C1—C6—C7 | 117.77 (12) | H16A—C16—H16B | 108.5 |
C5—C6—C7 | 123.35 (13) | C16—C17—H17A | 109.5 |
C14—C7—C6 | 117.96 (12) | C16—C17—H17B | 109.5 |
C14—C7—C8 | 122.12 (12) | H17A—C17—H17B | 109.5 |
C6—C7—C8 | 119.89 (12) | C16—C17—H17C | 109.5 |
C13—C8—C9 | 118.59 (14) | H17A—C17—H17C | 109.5 |
C13—C8—C7 | 120.19 (13) | H17B—C17—H17C | 109.5 |
C9—C8—C7 | 121.21 (13) | N1—C18—C14 | 122.27 (13) |
C10—C9—C8 | 120.56 (16) | N1—C18—C19 | 117.00 (14) |
C10—C9—H9 | 119.7 | C14—C18—C19 | 120.73 (13) |
C8—C9—H9 | 119.7 | C18—C19—H19A | 109.5 |
C11—C10—C9 | 120.00 (16) | C18—C19—H19B | 109.5 |
C11—C10—H10 | 120 | H19A—C19—H19B | 109.5 |
C9—C10—H10 | 120 | C18—C19—H19C | 109.5 |
C10—C11—C12 | 120.20 (16) | H19A—C19—H19C | 109.5 |
C10—C11—H11 | 119.9 | H19B—C19—H19C | 109.5 |
C12—C11—H11 | 119.9 | C18—N1—C1 | 118.58 (13) |
C11—C12—C13 | 119.94 (16) | C15—O2—C16 | 119.11 (13) |
N1—C1—C2—C3 | 178.06 (15) | C10—C11—C12—C13 | −0.8 (3) |
C6—C1—C2—C3 | −1.1 (2) | C9—C8—C13—C12 | 1.3 (2) |
C1—C2—C3—C4 | 0.8 (3) | C7—C8—C13—C12 | −177.08 (15) |
C2—C3—C4—C5 | 0.1 (3) | C11—C12—C13—C8 | −0.5 (3) |
C3—C4—C5—C6 | −0.6 (3) | C6—C7—C14—C18 | −0.5 (2) |
N1—C1—C6—C5 | −178.56 (13) | C8—C7—C14—C18 | 177.58 (12) |
C2—C1—C6—C5 | 0.6 (2) | C6—C7—C14—C15 | 178.33 (11) |
N1—C1—C6—C7 | 0.9 (2) | C8—C7—C14—C15 | −3.6 (2) |
C2—C1—C6—C7 | −179.97 (12) | C7—C14—C15—O1 | −76.8 (2) |
C4—C5—C6—C1 | 0.3 (2) | C18—C14—C15—O1 | 102.0 (2) |
C4—C5—C6—C7 | −179.12 (14) | C7—C14—C15—O2 | 102.89 (16) |
C1—C6—C7—C14 | −0.56 (19) | C18—C14—C15—O2 | −78.24 (17) |
C5—C6—C7—C14 | 178.85 (13) | C7—C14—C18—N1 | 1.5 (2) |
C1—C6—C7—C8 | −178.70 (12) | C15—C14—C18—N1 | −177.41 (13) |
C5—C6—C7—C8 | 0.7 (2) | C7—C14—C18—C19 | −177.80 (14) |
C14—C7—C8—C13 | −79.78 (18) | C15—C14—C18—C19 | 3.3 (2) |
C6—C7—C8—C13 | 98.29 (17) | C14—C18—N1—C1 | −1.1 (2) |
C14—C7—C8—C9 | 101.92 (17) | C19—C18—N1—C1 | 178.13 (13) |
C6—C7—C8—C9 | −80.01 (18) | C6—C1—N1—C18 | 0.0 (2) |
C13—C8—C9—C10 | −0.8 (2) | C2—C1—N1—C18 | −179.18 (13) |
C7—C8—C9—C10 | 177.53 (15) | O1—C15—O2—C16 | 0.8 (3) |
C8—C9—C10—C11 | −0.4 (3) | C14—C15—O2—C16 | −178.93 (15) |
C9—C10—C11—C12 | 1.2 (3) | C17—C16—O2—C15 | 129.54 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
C16—H16A···O1 | 0.97 | 2.32 | 2.711 (3) | 103 |
C19—H19B···O2i | 0.96 | 2.52 | 3.374 (3) | 147 |
C19—H19C···O2 | 0.96 | 2.59 | 3.212 (3) | 122 |
C12—H12···Cg2ii | 0.93 | 2.95 | 3.750 (3) | 145 |
C17—H17C···Cg3iii | 0.96 | 2.97 | 3.883 (3) | 160 |
Symmetry codes: (i) −x+1, −y−2, −z+1; (ii) −x+2, −y, −z+1; (iii) −x+2, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | C19H17NO2 |
Mr | 291.34 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 120 |
a, b, c (Å) | 9.0282 (10), 9.362 (1), 10.7258 (10) |
α, β, γ (°) | 69.765 (8), 66.733 (8), 70.605 (8) |
V (Å3) | 761.08 (15) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.35 × 0.32 × 0.25 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8164, 3995, 3410 |
Rint | 0.044 |
(sin θ/λ)max (Å−1) | 0.687 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.065, 0.194, 1.09 |
No. of reflections | 3995 |
No. of parameters | 199 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.33, −0.35 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXTL (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
C16—H16A···O1 | 0.97 | 2.32 | 2.711 (3) | 103 |
C19—H19B···O2i | 0.96 | 2.52 | 3.374 (3) | 147 |
C19—H19C···O2 | 0.96 | 2.59 | 3.212 (3) | 122 |
C12—H12···Cg2ii | 0.93 | 2.95 | 3.750 (3) | 145 |
C17—H17C···Cg3iii | 0.96 | 2.97 | 3.883 (3) | 160 |
Symmetry codes: (i) −x+1, −y−2, −z+1; (ii) −x+2, −y, −z+1; (iii) −x+2, −y, −z. |
Acknowledgements
The author is grateful to the Islamic Azad University, Dorood Branch, for financial support.
References
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Doube, D., Blouin, M., Brideau, C., Chan, C., Desmarais, S., Eithier, D., Falgueyert, J. P., Freisen, R. W., Girrard, M., Girrard, J., Tagari, P. & Yang, R. N. (1998). Bioorg. Med. Chem. Lett. 8, 1255–1260. Web of Science PubMed Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
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.
The quinoline moiety is probably the most well known heterocycle, a common and important feature of a variety of natural products and medicinal agents. They have emerged as antimalarial, antiasthmatic, anti-inflamatory, antibacterial, antihypertensive and tyrosine kinase PDGF-RTK inhibiting agents (Doube et al., 1998). Moreover, polyquinolines are found to undergo hierarchical self-assembly into a variety of nano and meso structures with enhanced electronic and photonic functions. We report herein the synthesis and crystal structure of the title compound.
In the molecule of the title compound (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. The quinoline ring system A (N1/C1–C7/C14/C18) is planar with a maximum deviaton of -0.021 (3) Å for atom C18, and oriented with respect to the phenyl ring B (C8–C13) at a dihedral angle of A/B = 80.44 (4)°. Intramolecular C—H···O interactions result in the formations of five- and six-membered rings C (O1/O2/C15/C16/H16A) and D (O2/C14/C15/C18/C19/H19C). Ring C is planar, while ring D adopts envelope conformation, with atom O2 displaced by -1.166 (4) Å from the plane of the other ring atoms.
In the crystal structure, intermolecular C—H···O interactions (Table 1) link the molecules into centrosymmetric dimers forming R22(12) ring motifs (Fig. 2) (Bernstein et al., 1995), in which they may be effective in the stabilization of the structure. The π–π contact between the rings of the quinoline ring system, Cg1···Cg2i [symmetry code: (i) 1 - x, -1 - y, 1 - z, where Cg1 and Cg2 are centroids of the rings (N1/C1/C6/C7/C14/C18) and (C1–C6), respectively] may further stabilize the structure, with centroid-centroid distance of 3.812 (1) Å. There also exist two weak C—H···π interactions (Table 1).