Novel chalcones derived from 2-chloro-3-formyl-6-methyl­quinoline

Mol­ecules of (E)-3-(2-chloro-6-methyl­quinolin-3-yl)-1-(5-iodo-2-­thienyl)prop-2-en-1-one, C₁₇H₁₁ClINOS, (I), and (E)-3-(2-chloro-6-methyl­quinolin-3-yl)-1-(5-methyl-2-­furyl)prop-2-en-1-one, C₁₈H₁₄ClNO₂, (II), adopt conformations slightly twisted from coplanarity. Both structures are devoid of classical hydrogen bonds. However, nonclassical C—H...O/N inter­actions [with C...O = 3.146 (5) Å and C...N = 3.487 (3) Å] link the mol­ecules into chains extended along the b axis in (I) and form dimers with an R₂²(8) motif in (II). The structural analysis of these compounds provides an insight into the correlation between mol­ecular structures and inter­molecular inter­actions in compounds for drug development.

S1. Comment

Chalcones, α,β-unsaturated ketones, constitute an important group of natural products that serve as precursors for the synthesis of different classes of flavonoids (Lin et al., 2002), pyrimidines, imidazoles (Varga et al., 2003) and 2-pyrazolines (Lévai, 2005). Some of them possess anticancer (Prabhavat & Ghiya, 1998), antimalarial (Wu et al., 2002), antituberculous, antitumour, anti-inflammatory, antiviral and antimicrobial activities (Opletalova & Sedivy, 1999). In order to correlate their molecular structures and intermolecular interactions with their biological manifestations, we have synthesised and determined the crystal structures of two new quinoline-based chalcones, namely (2E)-3-(2-chloro-6-methylquinolin-3-yl)-1-(5-iodothiophen-2-yl)prop-2-en-1-one, (I), and (2E)-3-(2-chloro-6-methylquinolin-3-yl)-1-(5-methylfuran-2-yl)prop-2-en-1-one, (II). A series of similar chalcones are under investigation for biological activity.

The molecule of (I) (Fig. 1) has the mean-planes of the 2-chloro-6-methylquinoline and (iodothiophen-2-yl)prop-2-en-1-one moieties inclined at 12.87 (6)°, resulting in a slightly twisted conformation. The maximum deviations of atoms Cl1 and C11 from these planes are 0.047 (2) and 0.048 (3) Å, respectively. The structure, without classical hydrogen bonds, contains interactions involving the thiophene atom H15 with the carbonyl atom O1 (Table 1), linking the molecules into chains along the (010) direction (Fig. 2). These chains are oriented in opposite directions, with the thiophene (S1/C13–C16) and benzene (C1–C6) ring centroids separated by 3.649 (3) Å (perpendicular distance 3.40 Å), indicating weak π–π interactions. The structure is also stabilized by intramolecular interactions, wherein atom H10 bonded to atom C10 of the propenone chain interacts with atoms O1 and Cl1 (Table 1).

In (II) (Fig. 3), the mean-planes of the 2-chloro-6-methylquinoline and (methylfuran-2-yl)prop-2-en-1-one moieties are inclined at 11.11 (5)° in a slightly twisted conformation similar to (I). The maximum deviations of atoms C3 and C10 from these planes are 0.039 (2) and 0.077 (2) Å, respectively. The structure of (II) is also without classical hydrogen bonds, but, unlike for (I), there are interactions involving atom H2 bonded to atom C2 and atom N1 of the quinoline ring system, C2—H2···N1ⁱ [C2···N1 = 3.487 (3) Å and C2—H2···N1ⁱ = 154°] which link the molecules into dimers (Fig. 4), forming eight-membered rings with an R₂²(8) motif (Bernstein et al., 1994). Unlike the π–π interactions observed in (I), the furan rings of the symmetry-related molecules in (II) lie parallel to each other with a distance of 3.798 (2) Å between the ring centroids. Moreover, a methyl H atom bonded to C18 is oriented towards the heterocyclic ring (N1/C1/C6–C9), with a perpendicular distance H18A···Cg = 2.82 Å (Cg is the centroid of the ring). The structure of (II) is also also stabilized by intramolecular interactions as in (I), i.e. C10—H10···O1 [C10···O1 = 2.780 (2) Å] and C10—H10···Cl1 [C10···Cl1 = 3.048 (2) Å] (Table 2).

The bond distances and angles in both structures are mostly in agreement with expected values (Orpen et al., 1994). The C12—C13—C14 angles have been widened to 131.1 (4) and 134.34 (18)° for (I) and (II), respectively, as reported in a large number of thiophene derivatives [Cambridge Structural Database (CSD), Version 5.29; Allen, 2002]. The C9—Cl1 bond distances in (I) and (II) of 1.765 (4) and 1.751 (2) Å, respectively, lie within the range (1.722–1.782 Å) of corresponding distances in 22 structures in the CSD containing the 2-chloroquinoline fragment, excluding those involved in metal complexes. The Cl1—C9—N1 and Cl1—C9—C8 angles of 114.4((3) and 118.2 (3)° in (I), and 114.52 (14) and 119.20 (15)° in (II), respectively, also lie within the ranges of the corresponding angles in related structures (112.0–118.2° and 116.4–121.2°, respectively). Furthermore, the C8—C10—C11 angles are significantly different in (I) and (II), at 125.5 (4) and 128.25 (18)°, respectively. The remaining angles lie within narrow ranges in both structures. A search of the CSD for 2-chloroquinoline moieties containing a C atom attached at position 3 revealed only the following structures: 2-chloro-3-(chloromethyl)quinoline (ATEDEI; Lu et al., 2003), 1,5-bis(4-chlorophenyl)-3-(2-chloroquinolin-3-yl)pentane-1,5-dione (MAZZET; Insuasty et al., 2006), (S)-2-(2-chloroquinolin-3-yl)-2-[(S)-α-methylbenzylamino]acetonitrile (MEHDAF; Belfaitah et al., 2006) and 2-chloro-3-(β-nitrovinyl)quinoline (QAMNAU; Palani et al., 2004).

Related literature

For related literature, see: Allen (2002); Belfaitah et al. (2006); Bernstein et al. (1994); Insuasty et al. (2006); Lévai (2005); Lin et al. (2002); Lu et al. (2003); Meth-Cohn (1981); Opletalova & Sedivy (1999); Orpen et al. (1994); Palani et al. (2004); Prabhavat & Ghiya (1998); Varga et al. (2003); Wu et al. (2002).

S2. Experimental

The precursor, 2-chloro-6-methyl-3-formylquinoline, was prepared using a literature procedure (Meth-Cohn et al., 1981). A mixture of 2-chloro-6-methyl-3-formylquinoline (2.055 g, 10 mmol) and 5-iodo-2-acetylthiophene (2.5207 g, 10 mmol) or 5-methyl-2-acetylfuran (1.2414 g, 10 mmol) in methanol (50 ml) was stirred at room temperature, followed by dropwise addition of aqueous NaOH (4 ml, 10%). The stirring was continued for 2 h and the reaction mixture was then kept at 273 K for 24 h. Subsequently, it was poured onto ice-cold water (200 ml). The precipitates were collected by filtration and washed with cold water followed by cold MeOH. The resulting chalcones were recrystallized from CHCl₃ to obtain yellow [Both compounds given as colourless in CIF tables - please check] solid crystalline products, (I) and (II).

Analysis for (I): m.p. 457–458 K; IR (neat, ν_max, cm^-1): C═O 1648 (s), C═C 1596 (m); ¹H NMR (400 MHz, CDCl₃, δ, p.p.m.): 2.54 (s, 3H, CH₃), 7.36 (d, 1H, H_4', J = 3.92 Hz), 7.37 (d, 1H, H_α, J = 15.54 Hz), 7.50 (d, 1H, H_3', J = 3.98 Hz), 7.59 (dd, 1H, H₇, J = 8.70 Hz), 7.62 (s, 1H, H₅), 7.90 (d, 1H, H₈, J = 8.54 Hz), 8.20 (d, 1H, H_β, J = 15.60 Hz), 8.35 (s, 1H, H₄); yield: 3.17 g, 7.21 mmol (72%).

Analysis for (II): m.p. 445–447 K; IR (neat, ν_max, cm^-1): C═O 1654 (s), C═C 1594 (m); ¹H NMR (400 MHz, CDCl₃, δ, p.p.m.): 2.45 (s, 3H, CH₃), 2.54 (s, 3H, CH₃), 6.24 (dd, 1H, H_4', J = 3.39 Hz), 7.29 (d, 1H, H_3', J = 3.45 Hz), 7.45 (d, 1H, H_α, J = 15.70 Hz), 7.58 (dd, 1H, H₇, J = 8.60 Hz), 7.63 (s, 1H, H₅), 7.90 (d, 1H, H₈, J = 8.58 Hz), 8.22 (d, 1H, H_β, J = 15.79 Hz), 8.38 (s, 1H, H₄); yield: 2.56 g, 8.21 mmol (82%).

S3. Refinement

For both structures, H atoms were included in the refinements in geometrically idealized positions, with aryl and methyl C—H distances of 0.95 and 0.98 Å, respectively, and U_iso = 1.2U_eq(C). The H atoms bonded to [Methyl?] atom C17 in (II) were [Equally?] disordered over six sites. The final difference maps were free of chemically significant features.

Computing details

For both compounds, data collection: COLLECT (Nonius, 1998); cell refinement: HKL DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures

	Fig. 1. The molecular structure of (I), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. Intermolecular interactions in the unit cell of (I), depicted as dashed lines. Only H atoms involved in interactions have been included. [Symmetry codes: (i) x, y+1, z; (ii) x, y-1, z.]
	Fig. 3. The molecular structure of (II), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 4. Intermolecular interactions in the dimeric unit of (II), depicted as dashed lines. Only H atoms involved in interactions have been included. [Symmetry codes: (i) -x, y, -z-1/2.]

(I) (2E)-3-(2-chloro-6-methylquinolin-3-yl)-1-(5-iodothiophen-2-yl)prop-2-en-1-one,

Crystal data

C17H11ClINOS	F(000) = 856
Mr = 439.68	Dx = 1.821 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6042 reflections
a = 17.112 (6) Å	θ = 3.0–27.5°
b = 7.636 (3) Å	µ = 2.29 mm^−1
c = 13.174 (5) Å	T = 173 K
β = 111.29 (2)°	Needle, colourless
V = 1603.9 (10) Å^3	0.26 × 0.07 × 0.06 mm
Z = 4

Data collection

Nonius KappaCCD diffractometer	3652 independent reflections
Radiation source: fine-focus sealed tube	2663 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
ω and ϕ scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −22→22
Tmin = 0.587, Tmax = 0.875	k = −9→8
6042 measured reflections	l = −16→16

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.097	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.034P)^2 + 2.3385P] where P = (Fo^2 + 2Fc^2)/3
3652 reflections	(Δ/σ)max = 0.001
200 parameters	Δρmax = 0.52 e Å^−3
0 restraints	Δρmin = −0.63 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
I1	0.477610 (18)	0.68986 (4)	0.85231 (3)	0.04444 (13)
Cl1	−0.01538 (6)	−0.32565 (11)	0.59179 (9)	0.0301 (2)
S1	0.36067 (6)	0.33286 (11)	0.80632 (9)	0.0269 (2)
O1	0.24498 (17)	0.0328 (3)	0.7570 (3)	0.0350 (7)
N1	−0.1516 (2)	−0.1431 (4)	0.5390 (3)	0.0242 (7)
C1	−0.1988 (2)	0.0076 (4)	0.5247 (3)	0.0238 (8)
C2	−0.2864 (2)	−0.0017 (5)	0.4749 (3)	0.0302 (9)
H2	−0.3129	−0.1113	0.4508	0.036*
C3	−0.3334 (3)	0.1471 (5)	0.4610 (3)	0.0313 (9)
H3	−0.3927	0.1387	0.4273	0.038*
C4	−0.2968 (3)	0.3139 (5)	0.4951 (3)	0.0267 (8)
C5	−0.2116 (3)	0.3249 (5)	0.5431 (3)	0.0280 (9)
H5	−0.1863	0.4359	0.5661	0.034*
C6	−0.1600 (2)	0.1738 (4)	0.5593 (3)	0.0224 (8)
C7	−0.0726 (2)	0.1781 (5)	0.6082 (3)	0.0255 (8)
H7	−0.0456	0.2870	0.6331	0.031*
C8	−0.0239 (2)	0.0280 (5)	0.6215 (3)	0.0239 (8)
C9	−0.0708 (2)	−0.1278 (5)	0.5833 (3)	0.0241 (8)
C10	0.0678 (2)	0.0337 (5)	0.6687 (3)	0.0266 (9)
H10	0.0965	−0.0751	0.6860	0.032*
C11	0.1141 (2)	0.1775 (5)	0.6893 (3)	0.0271 (9)
H11	0.0869	0.2883	0.6755	0.033*
C12	0.2068 (2)	0.1712 (5)	0.7331 (3)	0.0245 (8)
C13	0.2521 (2)	0.3381 (5)	0.7484 (3)	0.0220 (8)
C14	0.2237 (2)	0.5060 (5)	0.7258 (3)	0.0241 (8)
H14	0.1658	0.5348	0.6943	0.029*
C15	0.2881 (3)	0.6329 (5)	0.7534 (3)	0.0283 (9)
H15	0.2791	0.7553	0.7422	0.034*
C16	0.3644 (2)	0.5567 (5)	0.7981 (3)	0.0270 (9)
C17	−0.3517 (3)	0.4728 (5)	0.4795 (4)	0.0363 (10)
H17A	−0.3182	0.5785	0.4838	0.044*
H17B	−0.3758	0.4763	0.5366	0.044*
H17C	−0.3970	0.4672	0.4079	0.044*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.02682 (17)	0.03404 (17)	0.0658 (2)	−0.00876 (12)	0.00885 (15)	0.00075 (15)
Cl1	0.0307 (5)	0.0196 (4)	0.0396 (6)	0.0005 (4)	0.0122 (5)	0.0006 (4)
S1	0.0208 (5)	0.0202 (4)	0.0377 (6)	0.0033 (4)	0.0082 (4)	0.0027 (4)
O1	0.0310 (16)	0.0188 (14)	0.051 (2)	0.0008 (12)	0.0095 (14)	0.0006 (13)
N1	0.0277 (18)	0.0202 (15)	0.0261 (18)	−0.0044 (13)	0.0117 (15)	−0.0032 (13)
C1	0.029 (2)	0.0208 (18)	0.024 (2)	0.0008 (16)	0.0119 (17)	0.0003 (15)
C2	0.031 (2)	0.026 (2)	0.031 (2)	−0.0097 (17)	0.0074 (19)	−0.0032 (17)
C3	0.025 (2)	0.036 (2)	0.031 (2)	−0.0016 (17)	0.0068 (18)	−0.0008 (18)
C4	0.032 (2)	0.0224 (18)	0.025 (2)	0.0021 (16)	0.0087 (18)	0.0033 (16)
C5	0.031 (2)	0.0220 (19)	0.032 (2)	−0.0022 (16)	0.0132 (18)	0.0006 (17)
C6	0.025 (2)	0.0227 (18)	0.021 (2)	−0.0054 (15)	0.0109 (16)	−0.0020 (15)
C7	0.030 (2)	0.0197 (18)	0.028 (2)	−0.0045 (16)	0.0111 (18)	−0.0004 (16)
C8	0.027 (2)	0.0250 (18)	0.022 (2)	−0.0026 (16)	0.0115 (17)	0.0007 (16)
C9	0.029 (2)	0.0195 (17)	0.026 (2)	−0.0010 (16)	0.0125 (17)	0.0008 (15)
C10	0.026 (2)	0.0251 (19)	0.029 (2)	−0.0004 (16)	0.0104 (18)	−0.0001 (17)
C11	0.027 (2)	0.0244 (19)	0.030 (2)	0.0002 (16)	0.0105 (18)	0.0008 (17)
C12	0.026 (2)	0.0225 (19)	0.025 (2)	−0.0011 (16)	0.0089 (17)	0.0002 (16)
C13	0.0224 (19)	0.0217 (18)	0.0210 (19)	0.0003 (15)	0.0068 (16)	−0.0009 (15)
C14	0.0182 (19)	0.0243 (19)	0.029 (2)	0.0026 (15)	0.0072 (17)	0.0008 (16)
C15	0.030 (2)	0.0189 (18)	0.034 (2)	0.0022 (16)	0.0083 (19)	0.0045 (16)
C16	0.024 (2)	0.0223 (18)	0.033 (2)	−0.0037 (16)	0.0090 (18)	−0.0003 (17)
C17	0.034 (2)	0.031 (2)	0.041 (3)	0.0089 (19)	0.010 (2)	0.0015 (19)

Geometric parameters (Å, º)

I1—C16	2.072 (4)	C7—C8	1.390 (5)
Cl1—C9	1.765 (4)	C7—H7	0.9500
S1—C16	1.716 (4)	C8—C9	1.422 (5)
S1—C13	1.734 (4)	C8—C10	1.463 (5)
O1—C12	1.222 (4)	C10—C11	1.324 (5)
N1—C9	1.295 (5)	C10—H10	0.9500
N1—C1	1.379 (5)	C11—C12	1.480 (5)
C1—C2	1.402 (5)	C11—H11	0.9500
C1—C6	1.429 (5)	C12—C13	1.467 (5)
C2—C3	1.366 (5)	C13—C14	1.365 (5)
C2—H2	0.9500	C14—C15	1.413 (5)
C3—C4	1.419 (5)	C14—H14	0.9500
C3—H3	0.9500	C15—C16	1.353 (5)
C4—C5	1.365 (6)	C15—H15	0.9500
C4—C17	1.503 (5)	C17—H17A	0.9800
C5—C6	1.421 (5)	C17—H17B	0.9800
C5—H5	0.9500	C17—H17C	0.9800
C6—C7	1.397 (5)
C16—S1—C13	90.4 (2)	C8—C9—Cl1	118.2 (3)
C9—N1—C1	117.6 (3)	C11—C10—C8	125.5 (4)
N1—C1—C2	119.7 (3)	C11—C10—H10	117.2
N1—C1—C6	121.1 (3)	C8—C10—H10	117.2
C2—C1—C6	119.2 (3)	C10—C11—C12	122.0 (3)
C3—C2—C1	119.9 (3)	C10—C11—H11	119.0
C3—C2—H2	120.1	C12—C11—H11	119.0
C1—C2—H2	120.1	O1—C12—C13	120.6 (4)
C2—C3—C4	122.2 (4)	O1—C12—C11	121.8 (3)
C2—C3—H3	118.9	C13—C12—C11	117.6 (3)
C4—C3—H3	118.9	C14—C13—C12	131.1 (4)
C5—C4—C3	118.5 (3)	C14—C13—S1	111.0 (3)
C5—C4—C17	121.6 (3)	C12—C13—S1	117.9 (3)
C3—C4—C17	119.9 (4)	C13—C14—C15	113.9 (3)
C4—C5—C6	121.4 (3)	C13—C14—H14	123.0
C4—C5—H5	119.3	C15—C14—H14	123.0
C6—C5—H5	119.3	C16—C15—C14	110.9 (3)
C7—C6—C5	123.6 (3)	C16—C15—H15	124.6
C7—C6—C1	117.6 (3)	C14—C15—H15	124.6
C5—C6—C1	118.8 (3)	C15—C16—S1	113.8 (3)
C8—C7—C6	122.1 (3)	C15—C16—I1	124.9 (3)
C8—C7—H7	119.0	S1—C16—I1	121.2 (2)
C6—C7—H7	119.0	C4—C17—H17A	109.5
C7—C8—C9	114.2 (3)	C4—C17—H17B	109.5
C7—C8—C10	122.0 (3)	H17A—C17—H17B	109.5
C9—C8—C10	123.8 (3)	C4—C17—H17C	109.5
N1—C9—C8	127.4 (3)	H17A—C17—H17C	109.5
N1—C9—Cl1	114.4 (3)	H17B—C17—H17C	109.5
C9—N1—C1—C2	178.6 (4)	C10—C8—C9—N1	−178.7 (4)
C9—N1—C1—C6	−1.1 (5)	C7—C8—C9—Cl1	177.9 (3)
N1—C1—C2—C3	179.7 (4)	C10—C8—C9—Cl1	−0.7 (5)
C6—C1—C2—C3	−0.6 (6)	C7—C8—C10—C11	−9.8 (6)
C1—C2—C3—C4	0.2 (6)	C9—C8—C10—C11	168.7 (4)
C2—C3—C4—C5	0.2 (6)	C8—C10—C11—C12	−177.5 (4)
C2—C3—C4—C17	−179.0 (4)	C10—C11—C12—O1	−3.4 (6)
C3—C4—C5—C6	−0.2 (6)	C10—C11—C12—C13	177.3 (4)
C17—C4—C5—C6	179.0 (4)	O1—C12—C13—C14	178.3 (4)
C4—C5—C6—C7	−179.8 (4)	C11—C12—C13—C14	−2.4 (6)
C4—C5—C6—C1	−0.2 (6)	O1—C12—C13—S1	−2.6 (5)
N1—C1—C6—C7	−0.1 (5)	C11—C12—C13—S1	176.7 (3)
C2—C1—C6—C7	−179.7 (4)	C16—S1—C13—C14	−0.1 (3)
N1—C1—C6—C5	−179.7 (3)	C16—S1—C13—C12	−179.4 (3)
C2—C1—C6—C5	0.7 (5)	C12—C13—C14—C15	179.7 (4)
C5—C6—C7—C8	−179.2 (4)	S1—C13—C14—C15	0.5 (4)
C1—C6—C7—C8	1.2 (6)	C13—C14—C15—C16	−0.8 (5)
C6—C7—C8—C9	−1.2 (5)	C14—C15—C16—S1	0.7 (5)
C6—C7—C8—C10	177.5 (4)	C14—C15—C16—I1	−179.6 (3)
C1—N1—C9—C8	1.2 (6)	C13—S1—C16—C15	−0.4 (3)
C1—N1—C9—Cl1	−176.8 (3)	C13—S1—C16—I1	179.9 (2)
C7—C8—C9—N1	−0.1 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···Cl1	0.95	2.67	3.087 (4)	107
C10—H10···O1	0.95	2.51	2.826 (5)	100
C15—H15···O1^i	0.95	2.22	3.146 (5)	163

Symmetry code: (i) x, y+1, z.

(II) (2E)-3-(2-chloro-6-methylquinolin-3-yl)-1-(5-methylfuran-2-yl)prop-2-en-1-one

Crystal data

C18H14ClNO2	F(000) = 1296
Mr = 311.75	Dx = 1.403 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 6103 reflections
a = 36.228 (10) Å	θ = 3.2–27.4°
b = 7.372 (3) Å	µ = 0.27 mm^−1
c = 11.214 (5) Å	T = 173 K
β = 99.70 (2)°	Plate, colourless
V = 2952 (2) Å^3	0.22 × 0.20 × 0.07 mm
Z = 8

Data collection

Nonius KappaCCD diffractometer	3355 independent reflections
Radiation source: fine-focus sealed tube	2405 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
ω and ϕ scans	θmax = 27.4°, θmin = 3.2°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −45→46
Tmin = 0.944, Tmax = 0.982	k = −9→9
6103 measured reflections	l = −14→14

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.110	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.04P)^2 + 4.06P] where P = (Fo^2 + 2Fc^2)/3
3355 reflections	(Δ/σ)max < 0.001
200 parameters	Δρmax = 0.25 e Å^−3
0 restraints	Δρmin = −0.24 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1	0.089014 (14)	0.17647 (8)	0.03553 (4)	0.03435 (16)
O1	0.20865 (4)	0.4492 (2)	0.14894 (12)	0.0335 (4)
O2	0.27980 (4)	0.5478 (2)	0.13250 (12)	0.0257 (3)
N1	0.06106 (4)	0.1878 (2)	−0.19138 (14)	0.0254 (4)
C1	0.06078 (5)	0.2240 (3)	−0.31123 (17)	0.0232 (4)
C2	0.02713 (5)	0.1953 (3)	−0.39395 (18)	0.0285 (5)
H2	0.0054	0.1524	−0.3661	0.034*
C3	0.02624 (5)	0.2298 (3)	−0.51355 (19)	0.0297 (5)
H3	0.0035	0.2111	−0.5681	0.036*
C4	0.05801 (5)	0.2926 (3)	−0.55965 (18)	0.0255 (4)
C5	0.09051 (5)	0.3237 (3)	−0.47926 (17)	0.0235 (4)
H5	0.1120	0.3673	−0.5087	0.028*
C6	0.09271 (5)	0.2923 (3)	−0.35407 (17)	0.0216 (4)
C7	0.12495 (5)	0.3284 (3)	−0.26713 (17)	0.0215 (4)
H7	0.1468	0.3746	−0.2929	0.026*
C8	0.12524 (5)	0.2977 (3)	−0.14564 (17)	0.0220 (4)
C9	0.09148 (5)	0.2237 (3)	−0.11592 (17)	0.0234 (4)
C10	0.15695 (5)	0.3423 (3)	−0.05067 (17)	0.0233 (4)
H10	0.1533	0.3206	0.0300	0.028*
C11	0.19024 (5)	0.4092 (3)	−0.06317 (18)	0.0249 (4)
H11	0.1965	0.4275	−0.1412	0.030*
C12	0.21726 (5)	0.4546 (3)	0.04743 (17)	0.0238 (4)
C13	0.25448 (5)	0.5085 (3)	0.02898 (16)	0.0234 (4)
C14	0.27088 (5)	0.5352 (3)	−0.07028 (18)	0.0273 (5)
H14	0.2597	0.5176	−0.1524	0.033*
C15	0.30793 (5)	0.5946 (3)	−0.02707 (19)	0.0294 (5)
H15	0.3264	0.6248	−0.0748	0.035*
C16	0.31211 (5)	0.6001 (3)	0.09518 (18)	0.0256 (4)
C17	0.34329 (6)	0.6507 (3)	0.19331 (19)	0.0319 (5)
H17A	0.3352	0.6358	0.2719	0.048*	0.50
H17B	0.3503	0.7774	0.1832	0.048*	0.50
H17C	0.3649	0.5722	0.1896	0.048*	0.50
H17D	0.3651	0.6878	0.1579	0.048*	0.50
H17E	0.3500	0.5462	0.2466	0.048*	0.50
H17F	0.3354	0.7514	0.2402	0.048*	0.50
C18	0.05516 (6)	0.3215 (3)	−0.69376 (18)	0.0330 (5)
H18A	0.0791	0.3667	−0.7112	0.049*
H18B	0.0354	0.4103	−0.7213	0.049*
H18C	0.0491	0.2062	−0.7361	0.049*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0338 (3)	0.0486 (4)	0.0207 (3)	−0.0107 (2)	0.00478 (19)	0.0041 (2)
O1	0.0294 (8)	0.0524 (10)	0.0187 (7)	−0.0085 (7)	0.0037 (6)	−0.0013 (7)
O2	0.0226 (7)	0.0341 (8)	0.0192 (7)	−0.0042 (6)	0.0003 (5)	−0.0014 (6)
N1	0.0235 (8)	0.0309 (10)	0.0217 (8)	−0.0046 (7)	0.0043 (6)	−0.0012 (7)
C1	0.0215 (9)	0.0265 (11)	0.0218 (10)	−0.0013 (8)	0.0040 (7)	−0.0025 (8)
C2	0.0204 (9)	0.0374 (13)	0.0276 (10)	−0.0058 (9)	0.0042 (8)	−0.0027 (10)
C3	0.0224 (10)	0.0383 (13)	0.0261 (11)	−0.0038 (9)	−0.0025 (8)	−0.0015 (9)
C4	0.0265 (10)	0.0266 (11)	0.0225 (10)	−0.0011 (8)	0.0013 (8)	−0.0003 (9)
C5	0.0223 (9)	0.0257 (11)	0.0225 (10)	−0.0035 (8)	0.0043 (7)	0.0004 (9)
C6	0.0207 (9)	0.0230 (11)	0.0208 (9)	−0.0007 (8)	0.0025 (7)	−0.0017 (8)
C7	0.0176 (9)	0.0230 (10)	0.0245 (10)	−0.0011 (8)	0.0048 (7)	−0.0015 (8)
C8	0.0207 (9)	0.0237 (11)	0.0215 (9)	−0.0005 (8)	0.0029 (7)	−0.0008 (8)
C9	0.0254 (10)	0.0244 (11)	0.0206 (9)	0.0002 (8)	0.0044 (7)	−0.0006 (8)
C10	0.0245 (9)	0.0267 (11)	0.0181 (9)	0.0006 (8)	0.0019 (7)	0.0001 (8)
C11	0.0235 (10)	0.0303 (11)	0.0203 (10)	−0.0006 (8)	0.0020 (8)	−0.0003 (9)
C12	0.0245 (10)	0.0268 (11)	0.0196 (10)	−0.0004 (8)	0.0021 (7)	0.0012 (8)
C13	0.0235 (10)	0.0273 (11)	0.0175 (9)	−0.0025 (8)	−0.0019 (7)	−0.0009 (8)
C14	0.0297 (11)	0.0318 (12)	0.0202 (10)	−0.0014 (9)	0.0035 (8)	−0.0006 (9)
C15	0.0256 (10)	0.0360 (13)	0.0277 (11)	−0.0029 (9)	0.0074 (8)	−0.0001 (10)
C16	0.0230 (10)	0.0253 (11)	0.0286 (11)	−0.0024 (8)	0.0041 (8)	−0.0001 (9)
C17	0.0258 (10)	0.0379 (13)	0.0299 (11)	−0.0053 (9)	−0.0012 (8)	0.0001 (10)
C18	0.0333 (11)	0.0407 (14)	0.0229 (11)	−0.0058 (10)	−0.0013 (8)	0.0028 (10)

Geometric parameters (Å, º)

Cl1—C9	1.751 (2)	C10—C11	1.332 (3)
O1—C12	1.231 (2)	C10—H10	0.9500
O2—C16	1.364 (2)	C11—C12	1.483 (3)
O2—C13	1.383 (2)	C11—H11	0.9500
N1—C9	1.299 (2)	C12—C13	1.454 (3)
N1—C1	1.369 (2)	C13—C14	1.362 (3)
C1—C6	1.418 (3)	C14—C15	1.417 (3)
C1—C2	1.418 (3)	C14—H14	0.9500
C2—C3	1.360 (3)	C15—C16	1.354 (3)
C2—H2	0.9500	C15—H15	0.9500
C3—C4	1.417 (3)	C16—C17	1.485 (3)
C3—H3	0.9500	C17—H17A	0.9800
C4—C5	1.376 (3)	C17—H17B	0.9800
C4—C18	1.505 (3)	C17—H17C	0.9800
C5—C6	1.412 (3)	C17—H17D	0.9800
C5—H5	0.9500	C17—H17E	0.9800
C6—C7	1.415 (3)	C17—H17F	0.9800
C7—C8	1.379 (3)	C18—H18A	0.9800
C7—H7	0.9500	C18—H18B	0.9800
C8—C9	1.429 (3)	C18—H18C	0.9800
C8—C10	1.466 (3)
C16—O2—C13	106.48 (15)	C14—C13—C12	134.34 (18)
C9—N1—C1	117.70 (16)	O2—C13—C12	115.94 (16)
N1—C1—C6	122.05 (16)	C13—C14—C15	106.48 (18)
N1—C1—C2	118.47 (17)	C13—C14—H14	126.8
C6—C1—C2	119.47 (18)	C15—C14—H14	126.8
C3—C2—C1	119.50 (18)	C16—C15—C14	107.06 (18)
C3—C2—H2	120.2	C16—C15—H15	126.5
C1—C2—H2	120.2	C14—C15—H15	126.5
C2—C3—C4	122.35 (18)	C15—C16—O2	110.29 (17)
C2—C3—H3	118.8	C15—C16—C17	134.33 (19)
C4—C3—H3	118.8	O2—C16—C17	115.38 (17)
C5—C4—C3	118.26 (18)	C16—C17—H17A	109.5
C5—C4—C18	122.55 (18)	C16—C17—H17B	109.5
C3—C4—C18	119.19 (17)	H17A—C17—H17B	109.5
C4—C5—C6	121.53 (17)	C16—C17—H17C	109.5
C4—C5—H5	119.2	H17A—C17—H17C	109.5
C6—C5—H5	119.2	H17B—C17—H17C	109.5
C5—C6—C7	123.79 (17)	C16—C17—H17D	109.5
C5—C6—C1	118.85 (16)	H17A—C17—H17D	141.1
C7—C6—C1	117.35 (17)	H17B—C17—H17D	56.3
C8—C7—C6	121.17 (17)	H17C—C17—H17D	56.3
C8—C7—H7	119.4	C16—C17—H17E	109.5
C6—C7—H7	119.4	H17A—C17—H17E	56.3
C7—C8—C9	115.39 (17)	H17B—C17—H17E	141.1
C7—C8—C10	123.72 (17)	H17C—C17—H17E	56.3
C9—C8—C10	120.85 (17)	H17D—C17—H17E	109.5
N1—C9—C8	126.28 (18)	C16—C17—H17F	109.5
N1—C9—Cl1	114.52 (14)	H17A—C17—H17F	56.3
C8—C9—Cl1	119.20 (15)	H17B—C17—H17F	56.3
C11—C10—C8	128.25 (18)	H17C—C17—H17F	141.1
C11—C10—H10	115.9	H17D—C17—H17F	109.5
C8—C10—H10	115.9	H17E—C17—H17F	109.5
C10—C11—C12	118.51 (18)	C4—C18—H18A	109.5
C10—C11—H11	120.7	C4—C18—H18B	109.5
C12—C11—H11	120.7	H18A—C18—H18B	109.5
O1—C12—C13	121.76 (17)	C4—C18—H18C	109.5
O1—C12—C11	122.13 (17)	H18A—C18—H18C	109.5
C13—C12—C11	116.11 (17)	H18B—C18—H18C	109.5
C14—C13—O2	109.68 (17)
C9—N1—C1—C6	2.3 (3)	C10—C8—C9—N1	176.3 (2)
C9—N1—C1—C2	−176.46 (19)	C7—C8—C9—Cl1	179.13 (15)
N1—C1—C2—C3	−179.8 (2)	C10—C8—C9—Cl1	−3.0 (3)
C6—C1—C2—C3	1.5 (3)	C7—C8—C10—C11	−3.2 (3)
C1—C2—C3—C4	0.5 (3)	C9—C8—C10—C11	179.1 (2)
C2—C3—C4—C5	−1.7 (3)	C8—C10—C11—C12	176.17 (19)
C2—C3—C4—C18	177.9 (2)	C10—C11—C12—O1	−7.2 (3)
C3—C4—C5—C6	0.8 (3)	C10—C11—C12—C13	173.57 (19)
C18—C4—C5—C6	−178.8 (2)	C16—O2—C13—C14	0.3 (2)
C4—C5—C6—C7	−177.53 (19)	C16—O2—C13—C12	−178.12 (17)
C4—C5—C6—C1	1.2 (3)	O1—C12—C13—C14	−176.0 (2)
N1—C1—C6—C5	178.98 (19)	C11—C12—C13—C14	3.2 (4)
C2—C1—C6—C5	−2.3 (3)	O1—C12—C13—O2	1.8 (3)
N1—C1—C6—C7	−2.2 (3)	C11—C12—C13—O2	−178.97 (17)
C2—C1—C6—C7	176.48 (19)	O2—C13—C14—C15	−0.3 (2)
C5—C6—C7—C8	178.93 (19)	C12—C13—C14—C15	177.7 (2)
C1—C6—C7—C8	0.2 (3)	C13—C14—C15—C16	0.2 (2)
C6—C7—C8—C9	1.6 (3)	C14—C15—C16—O2	−0.1 (2)
C6—C7—C8—C10	−176.28 (18)	C14—C15—C16—C17	−179.5 (2)
C1—N1—C9—C8	−0.3 (3)	C13—O2—C16—C15	−0.1 (2)
C1—N1—C9—Cl1	179.01 (15)	C13—O2—C16—C17	179.47 (17)
C7—C8—C9—N1	−1.6 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···Cl1	0.95	2.57	3.048 (2)	111
C10—H10···O1	0.95	2.41	2.780 (2)	103
C2—H2···N1^i	0.95	2.61	3.487 (3)	154

Symmetry code: (i) −x, y, −z−1/2.