(E)-1-(2-Methyl-4-phenyl-quinolin-3-yl)-3-phenyl-prop-2-en-1-one.

In the title compound, C(25)H(19)NO, the quinoline ring system is approximately planar, with a maximum deviation of 0.32 (1) Å, and forms dihedral angles of 80.74 (3) and 81.71 (4)° with the two phenyl rings. In the crystal. mol-ecules are stacked along the b axis by way of a C-H⋯π inter-action and a weak π-π inter-action between the pyridine and phenyl rings with a centroid-centroid distance of 3.6924 (5) Å.

Related literature

For background to and the biological activity of quinoline derivatives, see: Morimoto et al. (1991 ▶); Michael (1997 ▶); Markees et al. (1970 ▶); Campbell et al. (1988) ▶; Maguire et al. (1994 ▶); Chen et al. (2001 ▶). For the biological activity of chalcones, see: Dimmock et al. (1999 ▶). For bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Loh, Fun, Sarveswari et al. (2010 ▶); Loh, Fun, Viji et al. (2010 ▶); Shahani et al. (2010 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C25H19NO

M = 349.41

Monoclinic,

a = 10.5830 (5) Å

b = 10.2189 (5) Å

c = 18.4509 (7) Å

β = 114.147 (2)°

V = 1820.80 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 100 K

0.57 × 0.48 × 0.35 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.957, T max = 0.973

27166 measured reflections

6509 independent reflections

5734 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.125

S = 1.05

6509 reflections

245 parameters

H-atom parameters constrained

Δρmax = 0.45 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811007057/is2680sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811007057/is2680Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C25H19NO	F(000) = 736
Mr = 349.41	Dx = 1.275 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9875 reflections
a = 10.5830 (5) Å	θ = 2.9–35.1°
b = 10.2189 (5) Å	µ = 0.08 mm−1
c = 18.4509 (7) Å	T = 100 K
β = 114.147 (2)°	Block, colourless
V = 1820.80 (14) Å3	0.57 × 0.48 × 0.35 mm
Z = 4

Bruker SMART APEXII DUO CCD area-detector diffractometer	6509 independent reflections
Radiation source: fine-focus sealed tube	5734 reflections with I > 2σ(I)
graphite	Rint = 0.024
φ and ω scans	θmax = 32.5°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −15→15
Tmin = 0.957, Tmax = 0.973	k = −15→15
27166 measured reflections	l = −27→27

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0699P)2 + 0.5003P] where P = (Fo2 + 2Fc2)/3
6509 reflections	(Δ/σ)max = 0.001
245 parameters	Δρmax = 0.45 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	0.08254 (7)	0.61008 (7)	0.74003 (4)	0.02139 (13)
N1	0.08585 (7)	0.73133 (7)	0.97579 (4)	0.01550 (13)
C1	0.41109 (8)	0.42498 (8)	0.90617 (5)	0.01661 (14)
H1A	0.4621	0.5004	0.9272	0.020*
C2	0.47170 (8)	0.32137 (9)	0.88288 (5)	0.01897 (15)
H2A	0.5635	0.3273	0.8895	0.023*
C3	0.39571 (9)	0.20934 (8)	0.84990 (5)	0.01841 (15)
H3A	0.4361	0.1406	0.8340	0.022*
C4	0.25883 (9)	0.20050 (8)	0.84073 (5)	0.01956 (15)
H4A	0.2073	0.1260	0.8182	0.023*
C5	0.19882 (8)	0.30296 (8)	0.86519 (5)	0.01787 (15)
H5A	0.1077	0.2959	0.8596	0.021*
C6	0.27412 (8)	0.41613 (7)	0.89806 (4)	0.01322 (13)
C7	0.20915 (7)	0.52474 (7)	0.92505 (4)	0.01297 (13)
C8	0.19789 (7)	0.51611 (7)	0.99939 (5)	0.01355 (13)
C9	0.24715 (8)	0.40797 (8)	1.05160 (5)	0.01717 (14)
H9A	0.2860	0.3367	1.0369	0.021*
C10	0.23797 (9)	0.40762 (9)	1.12373 (5)	0.02067 (16)
H10A	0.2705	0.3361	1.1575	0.025*
C11	0.17939 (9)	0.51514 (9)	1.14689 (5)	0.02056 (16)
H11A	0.1737	0.5143	1.1959	0.025*
C12	0.13073 (8)	0.62094 (8)	1.09741 (5)	0.01782 (15)
H12A	0.0927	0.6916	1.1132	0.021*
C13	0.13791 (7)	0.62353 (7)	1.02254 (5)	0.01411 (13)
C14	0.09416 (8)	0.73623 (7)	0.90660 (5)	0.01470 (14)
C15	0.15863 (7)	0.63547 (7)	0.87976 (4)	0.01344 (13)
C16	0.02989 (9)	0.85248 (8)	0.85478 (5)	0.02108 (16)
H16A	0.0019	0.9152	0.8841	0.032*
H16B	−0.0495	0.8248	0.8089	0.032*
H16C	0.0962	0.8918	0.8383	0.032*
C17	0.17065 (8)	0.65370 (7)	0.80187 (5)	0.01473 (14)
C18	0.28930 (8)	0.72866 (8)	0.80195 (5)	0.01588 (14)
H18A	0.2986	0.7388	0.7543	0.019*
C19	0.38512 (8)	0.78330 (7)	0.86795 (5)	0.01505 (14)
H19A	0.3747	0.7692	0.9150	0.018*
C20	0.50375 (8)	0.86236 (7)	0.87345 (5)	0.01548 (14)
C21	0.59080 (9)	0.91308 (8)	0.94763 (5)	0.01973 (15)
H21A	0.5724	0.8954	0.9918	0.024*
C22	0.70455 (9)	0.98962 (9)	0.95593 (6)	0.02567 (19)
H22A	0.7613	1.0235	1.0054	0.031*
C23	0.73351 (10)	1.01549 (9)	0.89041 (7)	0.02676 (19)
H23A	0.8094	1.0669	0.8959	0.032*
C24	0.64859 (10)	0.96426 (9)	0.81659 (6)	0.02460 (18)
H24A	0.6686	0.9807	0.7728	0.030*
C25	0.53413 (9)	0.88875 (8)	0.80779 (5)	0.01951 (15)
H25A	0.4774	0.8556	0.7581	0.023*

	U11	U22	U33	U12	U13	U23
O1	0.0222 (3)	0.0224 (3)	0.0164 (3)	−0.0036 (2)	0.0046 (2)	−0.0036 (2)
N1	0.0142 (3)	0.0149 (3)	0.0177 (3)	0.0010 (2)	0.0069 (2)	−0.0011 (2)
C1	0.0147 (3)	0.0170 (3)	0.0190 (3)	−0.0005 (2)	0.0079 (3)	−0.0020 (3)
C2	0.0164 (3)	0.0214 (4)	0.0209 (4)	0.0032 (3)	0.0095 (3)	−0.0004 (3)
C3	0.0228 (4)	0.0170 (3)	0.0172 (3)	0.0055 (3)	0.0099 (3)	0.0002 (3)
C4	0.0227 (4)	0.0153 (3)	0.0216 (4)	−0.0007 (3)	0.0100 (3)	−0.0044 (3)
C5	0.0163 (3)	0.0165 (3)	0.0216 (4)	−0.0016 (3)	0.0085 (3)	−0.0045 (3)
C6	0.0141 (3)	0.0129 (3)	0.0133 (3)	0.0012 (2)	0.0063 (2)	0.0000 (2)
C7	0.0123 (3)	0.0124 (3)	0.0147 (3)	−0.0005 (2)	0.0059 (2)	−0.0013 (2)
C8	0.0128 (3)	0.0130 (3)	0.0154 (3)	−0.0009 (2)	0.0064 (2)	−0.0007 (2)
C9	0.0201 (3)	0.0146 (3)	0.0174 (3)	0.0008 (3)	0.0083 (3)	0.0013 (3)
C10	0.0257 (4)	0.0188 (4)	0.0178 (4)	−0.0002 (3)	0.0093 (3)	0.0028 (3)
C11	0.0243 (4)	0.0231 (4)	0.0171 (3)	−0.0025 (3)	0.0114 (3)	−0.0006 (3)
C12	0.0184 (3)	0.0198 (3)	0.0182 (3)	−0.0017 (3)	0.0106 (3)	−0.0027 (3)
C13	0.0125 (3)	0.0145 (3)	0.0162 (3)	−0.0010 (2)	0.0068 (2)	−0.0016 (2)
C14	0.0139 (3)	0.0130 (3)	0.0165 (3)	0.0007 (2)	0.0054 (2)	−0.0008 (2)
C15	0.0131 (3)	0.0127 (3)	0.0146 (3)	−0.0005 (2)	0.0057 (2)	−0.0008 (2)
C16	0.0247 (4)	0.0167 (3)	0.0204 (4)	0.0068 (3)	0.0077 (3)	0.0025 (3)
C17	0.0165 (3)	0.0125 (3)	0.0148 (3)	0.0011 (2)	0.0061 (3)	0.0000 (2)
C18	0.0188 (3)	0.0154 (3)	0.0144 (3)	−0.0010 (2)	0.0078 (3)	0.0007 (2)
C19	0.0166 (3)	0.0146 (3)	0.0150 (3)	0.0001 (2)	0.0075 (3)	0.0007 (2)
C20	0.0163 (3)	0.0130 (3)	0.0180 (3)	0.0005 (2)	0.0078 (3)	0.0006 (2)
C21	0.0189 (3)	0.0182 (3)	0.0204 (4)	−0.0008 (3)	0.0064 (3)	−0.0012 (3)
C22	0.0199 (4)	0.0217 (4)	0.0310 (5)	−0.0037 (3)	0.0060 (3)	−0.0046 (3)
C23	0.0211 (4)	0.0192 (4)	0.0429 (6)	−0.0039 (3)	0.0161 (4)	−0.0020 (4)
C24	0.0265 (4)	0.0203 (4)	0.0351 (5)	−0.0021 (3)	0.0209 (4)	0.0006 (3)
C25	0.0228 (4)	0.0178 (3)	0.0220 (4)	−0.0016 (3)	0.0133 (3)	−0.0005 (3)

O1—C17	1.2244 (10)	C12—C13	1.4143 (11)
N1—C14	1.3159 (10)	C12—H12A	0.9300
N1—C13	1.3683 (10)	C14—C15	1.4309 (10)
C1—C2	1.3939 (11)	C14—C16	1.5020 (11)
C1—C6	1.3980 (10)	C15—C17	1.5054 (11)
C1—H1A	0.9300	C16—H16A	0.9600
C2—C3	1.3882 (12)	C16—H16B	0.9600
C2—H2A	0.9300	C16—H16C	0.9600
C3—C4	1.3910 (12)	C17—C18	1.4704 (11)
C3—H3A	0.9300	C18—C19	1.3464 (11)
C4—C5	1.3920 (11)	C18—H18A	0.9300
C4—H4A	0.9300	C19—C20	1.4611 (11)
C5—C6	1.3946 (11)	C19—H19A	0.9300
C5—H5A	0.9300	C20—C21	1.3997 (12)
C6—C7	1.4942 (10)	C20—C25	1.4009 (11)
C7—C15	1.3781 (10)	C21—C22	1.3905 (12)
C7—C8	1.4272 (11)	C21—H21A	0.9300
C8—C9	1.4178 (11)	C22—C23	1.3887 (15)
C8—C13	1.4186 (10)	C22—H22A	0.9300
C9—C10	1.3734 (12)	C23—C24	1.3912 (15)
C9—H9A	0.9300	C23—H23A	0.9300
C10—C11	1.4110 (13)	C24—C25	1.3886 (12)
C10—H10A	0.9300	C24—H24A	0.9300
C11—C12	1.3723 (12)	C25—H25A	0.9300
C11—H11A	0.9300
C14—N1—C13	118.22 (7)	N1—C14—C15	122.61 (7)
C2—C1—C6	120.38 (7)	N1—C14—C16	117.07 (7)
C2—C1—H1A	119.8	C15—C14—C16	120.31 (7)
C6—C1—H1A	119.8	C7—C15—C14	120.18 (7)
C3—C2—C1	120.29 (7)	C7—C15—C17	121.14 (7)
C3—C2—H2A	119.9	C14—C15—C17	118.68 (6)
C1—C2—H2A	119.9	C14—C16—H16A	109.5
C2—C3—C4	119.64 (7)	C14—C16—H16B	109.5
C2—C3—H3A	120.2	H16A—C16—H16B	109.5
C4—C3—H3A	120.2	C14—C16—H16C	109.5
C3—C4—C5	120.16 (8)	H16A—C16—H16C	109.5
C3—C4—H4A	119.9	H16B—C16—H16C	109.5
C5—C4—H4A	119.9	O1—C17—C18	121.00 (7)
C4—C5—C6	120.62 (7)	O1—C17—C15	121.00 (7)
C4—C5—H5A	119.7	C18—C17—C15	117.98 (6)
C6—C5—H5A	119.7	C19—C18—C17	122.95 (7)
C5—C6—C1	118.89 (7)	C19—C18—H18A	118.5
C5—C6—C7	120.13 (7)	C17—C18—H18A	118.5
C1—C6—C7	120.97 (7)	C18—C19—C20	126.87 (7)
C15—C7—C8	117.99 (7)	C18—C19—H19A	116.6
C15—C7—C6	121.67 (7)	C20—C19—H19A	116.6
C8—C7—C6	120.34 (6)	C21—C20—C25	118.83 (7)
C9—C8—C13	118.94 (7)	C21—C20—C19	118.42 (7)
C9—C8—C7	123.30 (7)	C25—C20—C19	122.75 (7)
C13—C8—C7	117.72 (7)	C22—C21—C20	120.66 (8)
C10—C9—C8	120.55 (7)	C22—C21—H21A	119.7
C10—C9—H9A	119.7	C20—C21—H21A	119.7
C8—C9—H9A	119.7	C23—C22—C21	120.04 (9)
C9—C10—C11	120.36 (8)	C23—C22—H22A	120.0
C9—C10—H10A	119.8	C21—C22—H22A	120.0
C11—C10—H10A	119.8	C22—C23—C24	119.77 (8)
C12—C11—C10	120.25 (8)	C22—C23—H23A	120.1
C12—C11—H11A	119.9	C24—C23—H23A	120.1
C10—C11—H11A	119.9	C25—C24—C23	120.45 (9)
C11—C12—C13	120.61 (8)	C25—C24—H24A	119.8
C11—C12—H12A	119.7	C23—C24—H24A	119.8
C13—C12—H12A	119.7	C24—C25—C20	120.25 (8)
N1—C13—C12	117.53 (7)	C24—C25—H25A	119.9
N1—C13—C8	123.19 (7)	C20—C25—H25A	119.9
C12—C13—C8	119.28 (7)
C6—C1—C2—C3	1.30 (13)	C7—C8—C13—C12	−177.19 (7)
C1—C2—C3—C4	−0.49 (13)	C13—N1—C14—C15	−1.81 (11)
C2—C3—C4—C5	−0.60 (13)	C13—N1—C14—C16	177.03 (7)
C3—C4—C5—C6	0.90 (13)	C8—C7—C15—C14	−1.49 (11)
C4—C5—C6—C1	−0.10 (12)	C6—C7—C15—C14	178.55 (7)
C4—C5—C6—C7	−179.22 (8)	C8—C7—C15—C17	178.10 (6)
C2—C1—C6—C5	−1.00 (12)	C6—C7—C15—C17	−1.87 (11)
C2—C1—C6—C7	178.11 (7)	N1—C14—C15—C7	3.21 (11)
C5—C6—C7—C15	−101.19 (9)	C16—C14—C15—C7	−175.58 (7)
C1—C6—C7—C15	79.71 (10)	N1—C14—C15—C17	−176.38 (7)
C5—C6—C7—C8	78.85 (10)	C16—C14—C15—C17	4.83 (11)
C1—C6—C7—C8	−100.25 (9)	C7—C15—C17—O1	86.75 (10)
C15—C7—C8—C9	−179.35 (7)	C14—C15—C17—O1	−93.66 (9)
C6—C7—C8—C9	0.62 (11)	C7—C15—C17—C18	−94.95 (9)
C15—C7—C8—C13	−1.28 (10)	C14—C15—C17—C18	84.63 (9)
C6—C7—C8—C13	178.68 (6)	O1—C17—C18—C19	176.95 (8)
C13—C8—C9—C10	−0.51 (12)	C15—C17—C18—C19	−1.35 (11)
C7—C8—C9—C10	177.53 (7)	C17—C18—C19—C20	−178.06 (7)
C8—C9—C10—C11	−0.06 (13)	C18—C19—C20—C21	178.74 (8)
C9—C10—C11—C12	0.17 (13)	C18—C19—C20—C25	−1.61 (13)
C10—C11—C12—C13	0.30 (13)	C25—C20—C21—C22	0.75 (12)
C14—N1—C13—C12	178.75 (7)	C19—C20—C21—C22	−179.58 (8)
C14—N1—C13—C8	−1.20 (11)	C20—C21—C22—C23	−0.58 (14)
C11—C12—C13—N1	179.18 (8)	C21—C22—C23—C24	−0.19 (14)
C11—C12—C13—C8	−0.87 (12)	C22—C23—C24—C25	0.78 (14)
C9—C8—C13—N1	−179.09 (7)	C23—C24—C25—C20	−0.60 (14)
C7—C8—C13—N1	2.76 (11)	C21—C20—C25—C24	−0.16 (12)
C9—C8—C13—C12	0.96 (11)	C19—C20—C25—C24	−179.82 (8)

Cg3 is the centroid of the C20–C25 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···Cg3i	0.93	2.72	3.5265 (10)	146

Table 1

Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C20–C25 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯Cg3i	0.93	2.72	3.5265 (10)	146

Symmetry code: (i) .