

Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S160053681002595X/lx2158sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S160053681002595X/lx2158Isup2.hkl |
CCDC reference: 746768
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean
(C-C) = 0.003 Å
- R factor = 0.040
- wR factor = 0.099
- Data-to-parameter ratio = 14.0
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 8 PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 4 PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 2
Alert level G PLAT380_ALERT_4_G Check Incorrectly? Oriented X(sp2)-Methyl Moiety C10
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
To a solution of 1-(6-chloro-2-hydroxy-4-phenylquinolin-3-yl)ethanone (1 mmol) in DMSO (5 ml) solution 2-chloro-3-chloromethyl-8-methylquinoline (1 mmol), Ag2SO4 (10 mol %) were added and refluxed at 383 K. The reaction was completed with in 20 min. The reaction mixture was then filtered and the supernatant liquid was added drop wise in to the crushed ice. The solution was neutralized with dilute HCl. The precipitate was filtered off and re-crystallized with ethanol. The clear solution was kept for a day and the resulting crystals were dried.
H atoms were positioned with idealized geometry using a riding model with C–H = 0.93-0.97 Å and refined as riding with Uiso(H) = 1.2-1.5Ueq(C).
In continuation of our previous work (Roopan et al., 2009; Khan, Roopan, Hathwar et al., 2010; Khan, Roopan, Kumar et al., 2010), we here report the molecular and crystal structure of 1-{6-chloro-2-[(2-chloro-8-methylquinolin-3-yl)methoxy]-4- phenylquinolin-3-yl}ethan-1-one. In the title molecule (I), (Fig. 1), the bond lengths (Allen et al., 1987) and angles observed are within normal ranges and are consistent with those related structures (Roopan et al., 2009; Khan, Roopan, Hathwar et al., 2010; Khan, Roopan, Kumar et al., 2010).
The quinoline rings (N1/C1-C9) and (N2/C12–C20) rings in (I) are almost planar, with maximal deviations from their mean planes of 0.016 (2) and of 0.042 (2) Å, respectively. These rings make a dihedral angle of 7.55 (6)° with each other. The N2/C12-C20 quinoline ring makes a dihedral angle of 62.59 (4)° with the C21-C26 phenyl ring. The molecular packing (Fig. 2) is stabilized by π–π stacking interactions between the quinoline rings of the adjacent molecules [Cg1···Cg2i = 3.771 (3) Å and Cg3···Cg4i = 3.612 (3) Å; where the Cg1, Cg2, Cg3 and Cg4 are the centroids of the N1/C1-C4/C9, N2/C12-C15/C20, C4-C9 and C15-C20 rings, respectively].
For the structures of related 2-quinolone compounds, see: Khan, Roopan, Hathwar et al. (2010); Khan, Roopan, Kumar et al. (2010). For the biological activity, see: Ukita & Mizuno (1960); Jayashree et al. (2010); Joseph et al. (2002); Xiao et al. (2001). For related literature, see: Roopan & Khan (2009). For bond-length data, see: Allen et al. (1987).
Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO CCD (Oxford Diffraction, 2009); data reduction: CrysAlis PRO RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).
C28H20Cl2N2O2 | Z = 2 |
Mr = 487.36 | F(000) = 504 |
Triclinic, P1 | Dx = 1.387 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.7396 (4) Å | Cell parameters from 1523 reflections |
b = 10.5520 (3) Å | θ = 1.9–21.4° |
c = 13.0108 (4) Å | µ = 0.31 mm−1 |
α = 88.730 (3)° | T = 295 K |
β = 68.127 (4)° | Block, colourless |
γ = 71.105 (4)° | 0.24 × 0.18 × 0.15 mm |
V = 1166.62 (8) Å3 |
Oxford Xcalibur Eos (Nova) CCD detector diffractometer | 4323 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 2707 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
ω scans | θmax = 25.5°, θmin = 3.3° |
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009) | h = −11→11 |
Tmin = 0.930, Tmax = 0.955 | k = −12→12 |
22437 measured reflections | l = −15→15 |
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)] = 0.040 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.099 | H-atom parameters constrained |
S = 0.95 | w = 1/[σ2(Fo2) + (0.0508P)2] where P = (Fo2 + 2Fc2)/3 |
4323 reflections | (Δ/σ)max < 0.001 |
309 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
C28H20Cl2N2O2 | γ = 71.105 (4)° |
Mr = 487.36 | V = 1166.62 (8) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.7396 (4) Å | Mo Kα radiation |
b = 10.5520 (3) Å | µ = 0.31 mm−1 |
c = 13.0108 (4) Å | T = 295 K |
α = 88.730 (3)° | 0.24 × 0.18 × 0.15 mm |
β = 68.127 (4)° |
Oxford Xcalibur Eos (Nova) CCD detector diffractometer | 4323 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009) | 2707 reflections with I > 2σ(I) |
Tmin = 0.930, Tmax = 0.955 | Rint = 0.043 |
22437 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.099 | H-atom parameters constrained |
S = 0.95 | Δρmax = 0.17 e Å−3 |
4323 reflections | Δρmin = −0.20 e Å−3 |
309 parameters |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 | ||
Cl1 | 0.16697 (6) | 0.85124 (6) | 1.16788 (4) | 0.0619 (2) | |
Cl2 | 0.24300 (8) | 0.10446 (6) | 0.58993 (5) | 0.0766 (3) | |
O1 | 0.8426 (2) | 0.46569 (18) | 0.71113 (15) | 0.0882 (8) | |
O2 | 0.51617 (15) | 0.59876 (14) | 0.85708 (11) | 0.0569 (5) | |
N1 | 0.40686 (19) | 0.91617 (16) | 1.15591 (12) | 0.0469 (6) | |
N2 | 0.34893 (19) | 0.50251 (15) | 0.83264 (13) | 0.0467 (6) | |
C1 | 0.3644 (2) | 0.83966 (19) | 1.10679 (15) | 0.0442 (7) | |
C2 | 0.4616 (2) | 0.74620 (18) | 1.01018 (15) | 0.0439 (7) | |
C3 | 0.6156 (2) | 0.73538 (19) | 0.96840 (15) | 0.0478 (7) | |
C4 | 0.6722 (2) | 0.81378 (19) | 1.01774 (15) | 0.0453 (7) | |
C5 | 0.8312 (2) | 0.8047 (2) | 0.97723 (17) | 0.0556 (8) | |
C6 | 0.8776 (3) | 0.8850 (2) | 1.02774 (19) | 0.0640 (9) | |
C7 | 0.7671 (3) | 0.9777 (2) | 1.11959 (18) | 0.0610 (9) | |
C8 | 0.6118 (3) | 0.9910 (2) | 1.16341 (16) | 0.0514 (8) | |
C9 | 0.5621 (2) | 0.90695 (19) | 1.11163 (15) | 0.0441 (7) | |
C10 | 0.4943 (3) | 1.0894 (2) | 1.26265 (18) | 0.0675 (9) | |
C11 | 0.3932 (2) | 0.6686 (2) | 0.96029 (15) | 0.0522 (7) | |
C12 | 0.4862 (2) | 0.51534 (18) | 0.79707 (16) | 0.0442 (7) | |
C13 | 0.6141 (2) | 0.45183 (18) | 0.69549 (15) | 0.0421 (7) | |
C14 | 0.5961 (2) | 0.36140 (18) | 0.63171 (15) | 0.0404 (6) | |
C15 | 0.4501 (2) | 0.33709 (18) | 0.67024 (15) | 0.0413 (7) | |
C16 | 0.4214 (2) | 0.2410 (2) | 0.61547 (16) | 0.0477 (7) | |
C17 | 0.2772 (3) | 0.2266 (2) | 0.65504 (17) | 0.0514 (8) | |
C18 | 0.1544 (3) | 0.3075 (2) | 0.74891 (18) | 0.0577 (8) | |
C19 | 0.1802 (2) | 0.3982 (2) | 0.80495 (17) | 0.0529 (8) | |
C20 | 0.3284 (2) | 0.41356 (19) | 0.76929 (16) | 0.0430 (7) | |
C21 | 0.7258 (2) | 0.29310 (18) | 0.52394 (15) | 0.0411 (7) | |
C22 | 0.7071 (2) | 0.3150 (2) | 0.42376 (17) | 0.0540 (8) | |
C23 | 0.8307 (3) | 0.2580 (2) | 0.32397 (17) | 0.0645 (9) | |
C24 | 0.9741 (3) | 0.1765 (2) | 0.32318 (18) | 0.0651 (9) | |
C25 | 0.9930 (3) | 0.1522 (2) | 0.42123 (18) | 0.0635 (8) | |
C26 | 0.8697 (2) | 0.2107 (2) | 0.52146 (17) | 0.0536 (8) | |
C27 | 0.7577 (2) | 0.4940 (2) | 0.66076 (18) | 0.0524 (7) | |
C28 | 0.7825 (3) | 0.5774 (2) | 0.56593 (19) | 0.0723 (9) | |
H3 | 0.68530 | 0.67470 | 0.90570 | 0.0570* | |
H5 | 0.90470 | 0.74350 | 0.91580 | 0.0670* | |
H6 | 0.98280 | 0.87830 | 1.00120 | 0.0770* | |
H7 | 0.80110 | 1.03260 | 1.15220 | 0.0730* | |
H10A | 0.54610 | 1.13850 | 1.28720 | 0.1010* | |
H10B | 0.44770 | 1.04160 | 1.32170 | 0.1010* | |
H10C | 0.41380 | 1.15120 | 1.24260 | 0.1010* | |
H11A | 0.35880 | 0.60500 | 1.00970 | 0.0630* | |
H11B | 0.30370 | 0.72910 | 0.94720 | 0.0630* | |
H16 | 0.50110 | 0.18710 | 0.55200 | 0.0570* | |
H18 | 0.05540 | 0.29910 | 0.77290 | 0.0690* | |
H19 | 0.09850 | 0.45120 | 0.86800 | 0.0630* | |
H22 | 0.61010 | 0.36870 | 0.42390 | 0.0650* | |
H23 | 0.81750 | 0.27460 | 0.25720 | 0.0770* | |
H24 | 1.05770 | 0.13810 | 0.25590 | 0.0780* | |
H25 | 1.08920 | 0.09610 | 0.42070 | 0.0760* | |
H26 | 0.88410 | 0.19420 | 0.58790 | 0.0640* | |
H28A | 0.86650 | 0.61000 | 0.55890 | 0.1090* | |
H28B | 0.68770 | 0.65240 | 0.57950 | 0.1090* | |
H28C | 0.80920 | 0.52340 | 0.49830 | 0.1090* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0520 (3) | 0.0709 (4) | 0.0580 (4) | −0.0276 (3) | −0.0098 (3) | −0.0047 (3) |
Cl2 | 0.0897 (5) | 0.0851 (5) | 0.0828 (5) | −0.0534 (4) | −0.0430 (4) | 0.0057 (3) |
O1 | 0.0757 (12) | 0.1028 (14) | 0.1176 (15) | −0.0422 (10) | −0.0617 (12) | 0.0225 (11) |
O2 | 0.0572 (9) | 0.0598 (9) | 0.0529 (9) | −0.0249 (7) | −0.0152 (7) | −0.0134 (7) |
N1 | 0.0549 (11) | 0.0459 (10) | 0.0428 (10) | −0.0199 (8) | −0.0197 (8) | 0.0048 (8) |
N2 | 0.0471 (10) | 0.0458 (10) | 0.0478 (10) | −0.0193 (8) | −0.0161 (8) | 0.0052 (8) |
C1 | 0.0488 (12) | 0.0439 (11) | 0.0408 (12) | −0.0193 (10) | −0.0156 (10) | 0.0086 (10) |
C2 | 0.0510 (13) | 0.0422 (11) | 0.0408 (11) | −0.0184 (10) | −0.0181 (10) | 0.0062 (9) |
C3 | 0.0511 (13) | 0.0486 (12) | 0.0386 (11) | −0.0150 (10) | −0.0134 (10) | 0.0014 (9) |
C4 | 0.0524 (13) | 0.0504 (12) | 0.0379 (11) | −0.0206 (10) | −0.0202 (10) | 0.0116 (9) |
C5 | 0.0545 (14) | 0.0657 (15) | 0.0462 (13) | −0.0266 (12) | −0.0140 (11) | 0.0126 (11) |
C6 | 0.0617 (15) | 0.0831 (18) | 0.0611 (15) | −0.0396 (14) | −0.0269 (13) | 0.0222 (13) |
C7 | 0.0809 (17) | 0.0671 (15) | 0.0625 (15) | −0.0458 (14) | −0.0407 (14) | 0.0208 (12) |
C8 | 0.0672 (15) | 0.0516 (13) | 0.0487 (13) | −0.0302 (12) | −0.0286 (11) | 0.0145 (10) |
C9 | 0.0558 (13) | 0.0446 (12) | 0.0395 (11) | −0.0217 (10) | −0.0229 (10) | 0.0114 (9) |
C10 | 0.0873 (17) | 0.0623 (15) | 0.0627 (15) | −0.0309 (13) | −0.0346 (13) | −0.0014 (12) |
C11 | 0.0544 (13) | 0.0519 (12) | 0.0483 (13) | −0.0168 (11) | −0.0183 (11) | −0.0042 (10) |
C12 | 0.0500 (13) | 0.0403 (11) | 0.0458 (12) | −0.0172 (10) | −0.0207 (10) | 0.0025 (9) |
C13 | 0.0418 (11) | 0.0413 (11) | 0.0450 (12) | −0.0144 (9) | −0.0185 (9) | 0.0062 (9) |
C14 | 0.0448 (11) | 0.0386 (11) | 0.0411 (11) | −0.0144 (9) | −0.0201 (9) | 0.0060 (9) |
C15 | 0.0486 (12) | 0.0386 (11) | 0.0418 (11) | −0.0174 (9) | −0.0212 (10) | 0.0098 (9) |
C16 | 0.0550 (13) | 0.0499 (12) | 0.0447 (12) | −0.0227 (11) | −0.0222 (10) | 0.0075 (9) |
C17 | 0.0618 (14) | 0.0523 (13) | 0.0585 (14) | −0.0310 (12) | −0.0337 (12) | 0.0147 (11) |
C18 | 0.0505 (13) | 0.0629 (15) | 0.0703 (16) | −0.0301 (12) | −0.0261 (12) | 0.0192 (12) |
C19 | 0.0463 (13) | 0.0521 (13) | 0.0592 (14) | −0.0206 (11) | −0.0161 (11) | 0.0068 (10) |
C20 | 0.0474 (12) | 0.0401 (11) | 0.0464 (12) | −0.0196 (10) | −0.0197 (10) | 0.0118 (9) |
C21 | 0.0455 (12) | 0.0387 (11) | 0.0418 (12) | −0.0178 (9) | −0.0168 (10) | 0.0040 (9) |
C22 | 0.0565 (13) | 0.0517 (13) | 0.0523 (14) | −0.0123 (11) | −0.0245 (11) | 0.0033 (10) |
C23 | 0.0849 (18) | 0.0627 (15) | 0.0420 (13) | −0.0204 (14) | −0.0241 (13) | 0.0041 (11) |
C24 | 0.0752 (17) | 0.0533 (14) | 0.0475 (14) | −0.0153 (13) | −0.0081 (12) | −0.0024 (11) |
C25 | 0.0551 (14) | 0.0559 (14) | 0.0611 (16) | −0.0030 (11) | −0.0159 (12) | 0.0009 (12) |
C26 | 0.0556 (14) | 0.0545 (13) | 0.0464 (13) | −0.0124 (11) | −0.0205 (11) | 0.0053 (10) |
C27 | 0.0436 (12) | 0.0462 (12) | 0.0654 (14) | −0.0130 (10) | −0.0201 (11) | −0.0070 (10) |
C28 | 0.0627 (15) | 0.0676 (15) | 0.0818 (17) | −0.0323 (13) | −0.0143 (13) | 0.0140 (13) |
Cl1—C1 | 1.749 (2) | C18—C19 | 1.354 (3) |
Cl2—C17 | 1.740 (3) | C19—C20 | 1.405 (3) |
O1—C27 | 1.199 (3) | C21—C22 | 1.386 (3) |
O2—C11 | 1.433 (2) | C21—C26 | 1.378 (3) |
O2—C12 | 1.355 (2) | C22—C23 | 1.378 (3) |
N1—C1 | 1.291 (3) | C23—C24 | 1.379 (4) |
N1—C9 | 1.373 (3) | C24—C25 | 1.363 (3) |
N2—C12 | 1.294 (3) | C25—C26 | 1.383 (3) |
N2—C20 | 1.371 (3) | C27—C28 | 1.491 (3) |
C1—C2 | 1.419 (3) | C3—H3 | 0.9300 |
C2—C3 | 1.357 (3) | C5—H5 | 0.9300 |
C2—C11 | 1.495 (3) | C6—H6 | 0.9300 |
C3—C4 | 1.408 (3) | C7—H7 | 0.9300 |
C4—C5 | 1.408 (3) | C10—H10A | 0.9600 |
C4—C9 | 1.415 (3) | C10—H10B | 0.9600 |
C5—C6 | 1.359 (3) | C10—H10C | 0.9600 |
C6—C7 | 1.398 (3) | C11—H11A | 0.9700 |
C7—C8 | 1.362 (4) | C11—H11B | 0.9700 |
C8—C9 | 1.422 (3) | C16—H16 | 0.9300 |
C8—C10 | 1.498 (3) | C18—H18 | 0.9300 |
C12—C13 | 1.421 (3) | C19—H19 | 0.9300 |
C13—C14 | 1.372 (3) | C22—H22 | 0.9300 |
C13—C27 | 1.511 (3) | C23—H23 | 0.9300 |
C14—C15 | 1.428 (3) | C24—H24 | 0.9300 |
C14—C21 | 1.489 (3) | C25—H25 | 0.9300 |
C15—C16 | 1.406 (3) | C26—H26 | 0.9300 |
C15—C20 | 1.416 (3) | C28—H28A | 0.9600 |
C16—C17 | 1.363 (4) | C28—H28B | 0.9600 |
C17—C18 | 1.396 (3) | C28—H28C | 0.9600 |
Cl1···C24i | 3.563 (2) | C13···H26 | 3.0100 |
Cl1···H11A | 2.9500 | C15···H22 | 3.0600 |
Cl1···H11B | 2.8100 | C16···H10Biii | 3.0600 |
Cl1···H24i | 2.9600 | C16···H22 | 3.0700 |
Cl1···H18ii | 2.9500 | C21···H16 | 2.6700 |
Cl1···H26iii | 3.0800 | C21···H28C | 2.7800 |
Cl2···H25iv | 3.1100 | C22···H28C | 3.0000 |
O1···O2 | 2.901 (2) | C22···H16 | 2.7900 |
O1···C18v | 3.169 (4) | C24···H5ix | 3.0900 |
O2···O1 | 2.901 (2) | C27···H26 | 3.0300 |
O1···H18v | 2.6200 | H3···O2 | 2.3300 |
O2···H3 | 2.3300 | H3···H5 | 2.5200 |
N1···H10B | 2.7700 | H5···H3 | 2.5200 |
N1···H10C | 2.7800 | H5···C24ix | 3.0900 |
N2···H11A | 2.6100 | H5···H24ix | 2.5000 |
N2···H11B | 2.6700 | H7···H10A | 2.3500 |
N2···H23vi | 2.8900 | H10A···H7 | 2.3500 |
C2···C8vii | 3.598 (3) | H10B···N1 | 2.7700 |
C4···C19iii | 3.543 (3) | H10B···C16iii | 3.0600 |
C5···C19iii | 3.504 (3) | H10C···N1 | 2.7800 |
C6···C18iii | 3.484 (3) | H10C···C3vii | 3.0400 |
C7···C18iii | 3.439 (3) | H11A···Cl1 | 2.9500 |
C7···C17iii | 3.579 (3) | H11A···N2 | 2.6100 |
C8···C2vii | 3.598 (3) | H11B···Cl1 | 2.8100 |
C8···C17iii | 3.475 (3) | H11B···N2 | 2.6700 |
C16···C22 | 3.275 (3) | H16···C21 | 2.6700 |
C17···C7iii | 3.579 (3) | H16···C22 | 2.7900 |
C17···C8iii | 3.475 (3) | H18···O1iv | 2.6200 |
C18···O1iv | 3.169 (4) | H18···Cl1ii | 2.9500 |
C18···C6iii | 3.484 (3) | H22···C15 | 3.0600 |
C18···C7iii | 3.439 (3) | H22···C16 | 3.0700 |
C19···C5iii | 3.504 (3) | H23···N2vi | 2.8900 |
C19···C4iii | 3.543 (3) | H24···Cl1viii | 2.9600 |
C21···C28 | 3.313 (3) | H24···C5ix | 2.9400 |
C22···C16 | 3.275 (3) | H24···H5ix | 2.5000 |
C24···Cl1viii | 3.563 (2) | H25···Cl2v | 3.1100 |
C26···C27 | 3.173 (3) | H26···C13 | 3.0100 |
C27···C26 | 3.173 (3) | H26···C27 | 3.0300 |
C28···C21 | 3.313 (3) | H26···Cl1iii | 3.0800 |
C3···H10Cvii | 3.0400 | H28B···C10vii | 3.0300 |
C5···H24ix | 2.9400 | H28C···C21 | 2.7800 |
C10···H28Bvii | 3.0300 | H28C···C22 | 3.0000 |
C11—O2—C12 | 118.02 (17) | C22—C23—C24 | 120.0 (2) |
C1—N1—C9 | 117.56 (16) | C23—C24—C25 | 119.9 (2) |
C12—N2—C20 | 116.71 (17) | C24—C25—C26 | 120.3 (2) |
Cl1—C1—N1 | 116.13 (15) | C21—C26—C25 | 120.7 (2) |
Cl1—C1—C2 | 117.06 (16) | O1—C27—C13 | 120.6 (2) |
N1—C1—C2 | 126.8 (2) | O1—C27—C28 | 122.5 (2) |
C1—C2—C3 | 115.30 (18) | C13—C27—C28 | 116.8 (2) |
C1—C2—C11 | 120.44 (18) | C2—C3—H3 | 119.00 |
C3—C2—C11 | 124.26 (17) | C4—C3—H3 | 119.00 |
C2—C3—C4 | 121.56 (17) | C4—C5—H5 | 120.00 |
C3—C4—C5 | 123.17 (18) | C6—C5—H5 | 120.00 |
C3—C4—C9 | 117.67 (19) | C5—C6—H6 | 120.00 |
C5—C4—C9 | 119.16 (19) | C7—C6—H6 | 120.00 |
C4—C5—C6 | 120.2 (2) | C6—C7—H7 | 119.00 |
C5—C6—C7 | 120.0 (3) | C8—C7—H7 | 119.00 |
C6—C7—C8 | 122.8 (2) | C8—C10—H10A | 109.00 |
C7—C8—C9 | 117.67 (19) | C8—C10—H10B | 109.00 |
C7—C8—C10 | 122.6 (2) | C8—C10—H10C | 109.00 |
C9—C8—C10 | 119.8 (2) | H10A—C10—H10B | 110.00 |
N1—C9—C4 | 121.05 (18) | H10A—C10—H10C | 109.00 |
N1—C9—C8 | 118.75 (18) | H10B—C10—H10C | 109.00 |
C4—C9—C8 | 120.2 (2) | O2—C11—H11A | 110.00 |
O2—C11—C2 | 106.18 (17) | O2—C11—H11B | 110.00 |
O2—C12—N2 | 119.90 (17) | C2—C11—H11A | 111.00 |
O2—C12—C13 | 114.06 (18) | C2—C11—H11B | 111.00 |
N2—C12—C13 | 126.01 (19) | H11A—C11—H11B | 109.00 |
C12—C13—C14 | 117.91 (19) | C15—C16—H16 | 120.00 |
C12—C13—C27 | 118.15 (17) | C17—C16—H16 | 120.00 |
C14—C13—C27 | 123.84 (17) | C17—C18—H18 | 120.00 |
C13—C14—C15 | 118.45 (17) | C19—C18—H18 | 120.00 |
C13—C14—C21 | 120.10 (19) | C18—C19—H19 | 119.00 |
C15—C14—C21 | 121.44 (17) | C20—C19—H19 | 119.00 |
C14—C15—C16 | 123.51 (17) | C21—C22—H22 | 120.00 |
C14—C15—C20 | 117.99 (18) | C23—C22—H22 | 120.00 |
C16—C15—C20 | 118.50 (19) | C22—C23—H23 | 120.00 |
C15—C16—C17 | 120.23 (18) | C24—C23—H23 | 120.00 |
Cl2—C17—C16 | 120.35 (16) | C23—C24—H24 | 120.00 |
Cl2—C17—C18 | 118.4 (2) | C25—C24—H24 | 120.00 |
C16—C17—C18 | 121.3 (2) | C24—C25—H25 | 120.00 |
C17—C18—C19 | 119.7 (3) | C26—C25—H25 | 120.00 |
C18—C19—C20 | 121.1 (2) | C21—C26—H26 | 120.00 |
N2—C20—C15 | 122.68 (19) | C25—C26—H26 | 120.00 |
N2—C20—C19 | 118.18 (18) | C27—C28—H28A | 110.00 |
C15—C20—C19 | 119.14 (19) | C27—C28—H28B | 109.00 |
C14—C21—C22 | 121.01 (18) | C27—C28—H28C | 109.00 |
C14—C21—C26 | 120.45 (17) | H28A—C28—H28B | 109.00 |
C22—C21—C26 | 118.49 (18) | H28A—C28—H28C | 109.00 |
C21—C22—C23 | 120.7 (2) | H28B—C28—H28C | 109.00 |
C12—O2—C11—C2 | 177.13 (15) | N2—C12—C13—C27 | 171.72 (18) |
C11—O2—C12—N2 | 1.1 (3) | C12—C13—C14—C15 | 0.5 (3) |
C11—O2—C12—C13 | 179.27 (16) | C12—C13—C14—C21 | 179.35 (17) |
C9—N1—C1—Cl1 | 178.38 (14) | C27—C13—C14—C15 | −175.59 (18) |
C9—N1—C1—C2 | −0.4 (3) | C27—C13—C14—C21 | 3.2 (3) |
C1—N1—C9—C4 | −2.0 (3) | C12—C13—C27—O1 | 69.7 (3) |
C1—N1—C9—C8 | 179.39 (18) | C12—C13—C27—C28 | −107.3 (2) |
C20—N2—C12—O2 | −178.21 (16) | C14—C13—C27—O1 | −114.2 (2) |
C20—N2—C12—C13 | 3.9 (3) | C14—C13—C27—C28 | 68.9 (3) |
C12—N2—C20—C15 | 0.8 (3) | C13—C14—C15—C16 | −176.10 (18) |
C12—N2—C20—C19 | −179.37 (18) | C13—C14—C15—C20 | 3.5 (3) |
Cl1—C1—C2—C3 | −176.91 (14) | C21—C14—C15—C16 | 5.1 (3) |
Cl1—C1—C2—C11 | 3.7 (2) | C21—C14—C15—C20 | −175.27 (17) |
N1—C1—C2—C3 | 1.9 (3) | C13—C14—C21—C22 | −115.6 (2) |
N1—C1—C2—C11 | −177.46 (18) | C13—C14—C21—C26 | 61.7 (3) |
C1—C2—C3—C4 | −0.9 (3) | C15—C14—C21—C22 | 63.2 (3) |
C11—C2—C3—C4 | 178.43 (18) | C15—C14—C21—C26 | −119.5 (2) |
C1—C2—C11—O2 | 172.29 (16) | C14—C15—C16—C17 | −177.72 (19) |
C3—C2—C11—O2 | −7.0 (2) | C20—C15—C16—C17 | 2.7 (3) |
C2—C3—C4—C5 | 179.57 (19) | C14—C15—C20—N2 | −4.4 (3) |
C2—C3—C4—C9 | −1.3 (3) | C14—C15—C20—C19 | 175.73 (18) |
C3—C4—C5—C6 | 178.91 (19) | C16—C15—C20—N2 | 175.24 (18) |
C9—C4—C5—C6 | −0.2 (3) | C16—C15—C20—C19 | −4.6 (3) |
C3—C4—C9—N1 | 2.8 (3) | C15—C16—C17—Cl2 | −178.09 (15) |
C3—C4—C9—C8 | −178.59 (18) | C15—C16—C17—C18 | 1.1 (3) |
C5—C4—C9—N1 | −177.99 (18) | Cl2—C17—C18—C19 | 176.30 (17) |
C5—C4—C9—C8 | 0.6 (3) | C16—C17—C18—C19 | −2.9 (3) |
C4—C5—C6—C7 | −0.5 (3) | C17—C18—C19—C20 | 0.8 (3) |
C5—C6—C7—C8 | 1.0 (3) | C18—C19—C20—N2 | −176.95 (19) |
C6—C7—C8—C9 | −0.6 (3) | C18—C19—C20—C15 | 2.9 (3) |
C6—C7—C8—C10 | 179.3 (2) | C14—C21—C22—C23 | 176.0 (2) |
C7—C8—C9—N1 | 178.44 (18) | C26—C21—C22—C23 | −1.4 (3) |
C7—C8—C9—C4 | −0.2 (3) | C14—C21—C26—C25 | −176.8 (2) |
C10—C8—C9—N1 | −1.5 (3) | C22—C21—C26—C25 | 0.6 (3) |
C10—C8—C9—C4 | 179.92 (19) | C21—C22—C23—C24 | 1.0 (3) |
O2—C12—C13—C14 | 177.38 (17) | C22—C23—C24—C25 | 0.2 (4) |
O2—C12—C13—C27 | −6.3 (2) | C23—C24—C25—C26 | −1.1 (4) |
N2—C12—C13—C14 | −4.6 (3) | C24—C25—C26—C21 | 0.7 (3) |
Symmetry codes: (i) x−1, y+1, z+1; (ii) −x, −y+1, −z+2; (iii) −x+1, −y+1, −z+2; (iv) x−1, y, z; (v) x+1, y, z; (vi) −x+1, −y+1, −z+1; (vii) −x+1, −y+2, −z+2; (viii) x+1, y−1, z−1; (ix) −x+2, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C28H20Cl2N2O2 |
Mr | 487.36 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 295 |
a, b, c (Å) | 9.7396 (4), 10.5520 (3), 13.0108 (4) |
α, β, γ (°) | 88.730 (3), 68.127 (4), 71.105 (4) |
V (Å3) | 1166.62 (8) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.31 |
Crystal size (mm) | 0.24 × 0.18 × 0.15 |
Data collection | |
Diffractometer | Oxford Xcalibur Eos (Nova) CCD detector |
Absorption correction | Multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009) |
Tmin, Tmax | 0.930, 0.955 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 22437, 4323, 2707 |
Rint | 0.043 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.099, 0.95 |
No. of reflections | 4323 |
No. of parameters | 309 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.17, −0.20 |
Computer programs: CrysAlis PRO CCD (Oxford Diffraction, 2009), CrysAlis PRO RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).
In continuation of our previous work (Roopan et al., 2009; Khan, Roopan, Hathwar et al., 2010; Khan, Roopan, Kumar et al., 2010), we here report the molecular and crystal structure of 1-{6-chloro-2-[(2-chloro-8-methylquinolin-3-yl)methoxy]-4- phenylquinolin-3-yl}ethan-1-one. In the title molecule (I), (Fig. 1), the bond lengths (Allen et al., 1987) and angles observed are within normal ranges and are consistent with those related structures (Roopan et al., 2009; Khan, Roopan, Hathwar et al., 2010; Khan, Roopan, Kumar et al., 2010).
The quinoline rings (N1/C1-C9) and (N2/C12–C20) rings in (I) are almost planar, with maximal deviations from their mean planes of 0.016 (2) and of 0.042 (2) Å, respectively. These rings make a dihedral angle of 7.55 (6)° with each other. The N2/C12-C20 quinoline ring makes a dihedral angle of 62.59 (4)° with the C21-C26 phenyl ring. The molecular packing (Fig. 2) is stabilized by π–π stacking interactions between the quinoline rings of the adjacent molecules [Cg1···Cg2i = 3.771 (3) Å and Cg3···Cg4i = 3.612 (3) Å; where the Cg1, Cg2, Cg3 and Cg4 are the centroids of the N1/C1-C4/C9, N2/C12-C15/C20, C4-C9 and C15-C20 rings, respectively].