(2E)-3-(4-Bromo-phen-yl)-1-(2-methyl-4-phenyl-3-quinol-yl)prop-2-en-1-one.

The conformation about the ethene bond [1.316 (3) Å] in the title compound, C(25)H(18)BrNO, is E. The quinoline ring forms dihedral angles of 67.21 (10) and 71.68 (10)° with the benzene and bromo-substituted benzene rings, respectively. Highlighting the non-planar arrangement of aromatic rings, the dihedral angle formed between the benzene rings is 58.57 (12)°.

Related literature

For general background to quinoline derivatives, see: Morimoto et al. (1991 ▶); Michael (1997 ▶); Markees et al. (1970 ▶); Campbell et al. (1998 ▶); Maguire et al. (1994 ▶); Kalluraya & Sreenivasa (1998 ▶); Roma et al. (2000 ▶); Chen et al. (2001 ▶). For inter­est in the biological activities of chalcones, see: Dimmock et al. (1999 ▶).

Experimental

Crystal data

C25H18BrNO

M = 428.31

Triclinic,

a = 6.6407 (3) Å

b = 10.0395 (4) Å

c = 15.5193 (6) Å

α = 92.192 (2)°

β = 95.234 (2)°

γ = 105.869 (2)°

V = 988.92 (7) Å3

Z = 2

Mo Kα radiation

μ = 2.09 mm−1

T = 293 K

0.28 × 0.21 × 0.14 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.596, T max = 0.746

15973 measured reflections

3470 independent reflections

2545 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.083

S = 1.01

3470 reflections

254 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.35 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) and PLATON (Spek, 2009 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810013784/hg2673sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810013784/hg2673Isup2.hkl

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

C25H18BrNO	Z = 2
Mr = 428.31	F(000) = 436
Triclinic, P1	Dx = 1.438 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.6407 (3) Å	Cell parameters from 4795 reflections
b = 10.0395 (4) Å	θ = 2.6–23.7°
c = 15.5193 (6) Å	µ = 2.09 mm−1
α = 92.192 (2)°	T = 293 K
β = 95.234 (2)°	Plate, colourless
γ = 105.869 (2)°	0.28 × 0.21 × 0.14 mm
V = 988.92 (7) Å3

Bruker SMART APEX CCD diffractometer	3470 independent reflections
Radiation source: fine-focus sealed tube	2545 reflections with I > 2σ(I)
graphite	Rint = 0.027
ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −7→7
Tmin = 0.596, Tmax = 0.746	k = −11→11
15973 measured reflections	l = −18→18

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0378P)2 + 0.3122P] where P = (Fo2 + 2Fc2)/3
3470 reflections	(Δ/σ)max = 0.001
254 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.35 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
Br1	0.08613 (5)	0.24943 (4)	0.49005 (2)	0.08720 (16)
O1	1.1467 (3)	0.65490 (17)	0.15079 (12)	0.0608 (5)
N1	0.7271 (3)	0.91386 (18)	0.04962 (12)	0.0419 (4)
C1	0.8532 (3)	1.0419 (2)	0.07979 (14)	0.0377 (5)
C2	0.8037 (4)	1.1593 (2)	0.04646 (15)	0.0475 (6)
H2	0.6909	1.1479	0.0040	0.057*
C3	0.9207 (4)	1.2891 (2)	0.07632 (17)	0.0540 (6)
H3	0.8868	1.3658	0.0541	0.065*
C4	1.0909 (4)	1.3087 (2)	0.13987 (16)	0.0527 (6)
H4	1.1685	1.3982	0.1598	0.063*
C5	1.1440 (4)	1.1977 (2)	0.17279 (14)	0.0431 (5)
H5	1.2583	1.2119	0.2148	0.052*
C6	1.0268 (3)	1.0609 (2)	0.14360 (13)	0.0348 (5)
C7	1.0703 (3)	0.9398 (2)	0.17656 (13)	0.0344 (5)
C8	0.9391 (3)	0.8119 (2)	0.14548 (14)	0.0361 (5)
C9	0.7675 (3)	0.8033 (2)	0.08138 (14)	0.0395 (5)
C10	1.2501 (3)	0.9522 (2)	0.24382 (13)	0.0361 (5)
C11	1.4566 (4)	1.0046 (3)	0.22479 (16)	0.0522 (6)
H11	1.4833	1.0335	0.1697	0.063*
C12	1.6221 (4)	1.0137 (3)	0.28757 (19)	0.0627 (7)
H12	1.7597	1.0486	0.2743	0.075*
C13	1.5861 (4)	0.9721 (3)	0.36906 (18)	0.0591 (7)
H13	1.6984	0.9783	0.4109	0.071*
C14	1.3823 (4)	0.9209 (3)	0.38841 (16)	0.0563 (6)
H14	1.3568	0.8921	0.4436	0.068*
C15	1.2162 (4)	0.9120 (2)	0.32667 (14)	0.0451 (5)
H15	1.0791	0.8784	0.3409	0.054*
C16	0.9910 (4)	0.6815 (2)	0.17362 (15)	0.0433 (5)
C17	0.8555 (4)	0.5880 (2)	0.22805 (16)	0.0488 (6)
H17	0.8854	0.5047	0.2391	0.059*
C18	0.6945 (4)	0.6130 (2)	0.26255 (15)	0.0457 (6)
H18	0.6660	0.6964	0.2503	0.055*
C19	0.5548 (3)	0.5238 (2)	0.31818 (15)	0.0444 (5)
C20	0.3842 (4)	0.5633 (3)	0.34362 (17)	0.0547 (6)
H20	0.3621	0.6461	0.3258	0.066*
C21	0.2463 (4)	0.4832 (3)	0.39470 (17)	0.0602 (7)
H21	0.1321	0.5112	0.4110	0.072*
C22	0.2791 (4)	0.3614 (3)	0.42126 (16)	0.0524 (6)
C23	0.4469 (4)	0.3192 (3)	0.39775 (17)	0.0580 (7)
H23	0.4680	0.2365	0.4161	0.070*
C24	0.5839 (4)	0.4003 (2)	0.34676 (17)	0.0550 (6)
H24	0.6984	0.3719	0.3311	0.066*
C26	0.6217 (4)	0.6658 (2)	0.04495 (17)	0.0538 (6)
H26A	0.5103	0.6364	0.0813	0.081*
H26B	0.6990	0.5979	0.0430	0.081*
H26C	0.5630	0.6755	−0.0126	0.081*

	U11	U22	U33	U12	U13	U23
Br1	0.0736 (2)	0.0933 (3)	0.0832 (2)	−0.00470 (17)	0.02395 (17)	0.03235 (18)
O1	0.0616 (11)	0.0476 (10)	0.0839 (13)	0.0264 (8)	0.0242 (10)	0.0157 (9)
N1	0.0385 (10)	0.0394 (11)	0.0463 (11)	0.0092 (8)	0.0020 (8)	0.0015 (9)
C1	0.0377 (11)	0.0369 (13)	0.0403 (12)	0.0122 (10)	0.0072 (10)	0.0035 (10)
C2	0.0487 (13)	0.0461 (15)	0.0498 (14)	0.0180 (11)	−0.0005 (11)	0.0081 (11)
C3	0.0643 (16)	0.0394 (14)	0.0637 (16)	0.0230 (12)	0.0047 (13)	0.0121 (12)
C4	0.0617 (15)	0.0318 (13)	0.0623 (16)	0.0101 (11)	0.0052 (13)	−0.0014 (11)
C5	0.0463 (12)	0.0377 (13)	0.0433 (13)	0.0099 (10)	0.0007 (10)	0.0001 (10)
C6	0.0382 (11)	0.0316 (12)	0.0363 (12)	0.0102 (9)	0.0106 (9)	0.0029 (9)
C7	0.0337 (11)	0.0359 (12)	0.0355 (11)	0.0104 (9)	0.0099 (9)	0.0041 (9)
C8	0.0365 (11)	0.0323 (12)	0.0402 (12)	0.0088 (9)	0.0095 (10)	0.0049 (9)
C9	0.0383 (11)	0.0347 (12)	0.0446 (13)	0.0079 (9)	0.0080 (10)	0.0004 (10)
C10	0.0407 (12)	0.0288 (11)	0.0399 (12)	0.0116 (9)	0.0046 (10)	0.0006 (9)
C11	0.0430 (13)	0.0664 (16)	0.0482 (14)	0.0145 (12)	0.0112 (12)	0.0039 (12)
C12	0.0369 (13)	0.0794 (19)	0.0726 (19)	0.0188 (13)	0.0062 (13)	−0.0074 (15)
C13	0.0556 (16)	0.0624 (17)	0.0600 (18)	0.0249 (13)	−0.0123 (13)	−0.0056 (13)
C14	0.0676 (17)	0.0538 (15)	0.0437 (14)	0.0131 (13)	−0.0052 (13)	0.0080 (11)
C15	0.0448 (13)	0.0447 (13)	0.0422 (13)	0.0059 (10)	0.0050 (11)	0.0061 (10)
C16	0.0461 (13)	0.0340 (12)	0.0482 (14)	0.0087 (10)	0.0048 (11)	0.0029 (10)
C17	0.0563 (14)	0.0332 (13)	0.0579 (15)	0.0122 (11)	0.0097 (12)	0.0089 (11)
C18	0.0529 (14)	0.0315 (12)	0.0524 (14)	0.0111 (10)	0.0051 (12)	0.0043 (10)
C19	0.0467 (13)	0.0358 (13)	0.0469 (14)	0.0058 (10)	0.0025 (11)	0.0035 (10)
C20	0.0575 (15)	0.0472 (14)	0.0639 (16)	0.0184 (12)	0.0138 (13)	0.0121 (12)
C21	0.0506 (15)	0.0665 (18)	0.0658 (17)	0.0163 (13)	0.0162 (13)	0.0077 (14)
C22	0.0493 (14)	0.0513 (15)	0.0471 (14)	−0.0020 (12)	0.0036 (11)	0.0073 (11)
C23	0.0620 (16)	0.0439 (14)	0.0653 (17)	0.0088 (12)	0.0061 (13)	0.0146 (12)
C24	0.0489 (14)	0.0479 (15)	0.0687 (17)	0.0117 (11)	0.0122 (13)	0.0087 (13)
C26	0.0485 (13)	0.0431 (14)	0.0615 (16)	0.0026 (11)	−0.0037 (12)	−0.0033 (12)

Br1—C22	1.897 (2)	C12—H12	0.9300
O1—C16	1.215 (3)	C13—C14	1.375 (4)
N1—C9	1.314 (3)	C13—H13	0.9300
N1—C1	1.367 (3)	C14—C15	1.375 (3)
C1—C2	1.411 (3)	C14—H14	0.9300
C1—C6	1.415 (3)	C15—H15	0.9300
C2—C3	1.360 (3)	C16—C17	1.463 (3)
C2—H2	0.9300	C17—C18	1.316 (3)
C3—C4	1.396 (3)	C17—H17	0.9300
C3—H3	0.9300	C18—C19	1.469 (3)
C4—C5	1.361 (3)	C18—H18	0.9300
C4—H4	0.9300	C19—C20	1.383 (3)
C5—C6	1.415 (3)	C19—C24	1.389 (3)
C5—H5	0.9300	C20—C21	1.376 (3)
C6—C7	1.427 (3)	C20—H20	0.9300
C7—C8	1.380 (3)	C21—C22	1.371 (4)
C7—C10	1.487 (3)	C21—H21	0.9300
C8—C9	1.424 (3)	C22—C23	1.369 (4)
C8—C16	1.513 (3)	C23—C24	1.376 (3)
C9—C26	1.507 (3)	C23—H23	0.9300
C10—C15	1.382 (3)	C24—H24	0.9300
C10—C11	1.392 (3)	C26—H26A	0.9600
C11—C12	1.381 (3)	C26—H26B	0.9600
C11—H11	0.9300	C26—H26C	0.9600
C12—C13	1.368 (4)
C9—N1—C1	118.80 (18)	C15—C14—C13	120.4 (2)
N1—C1—C2	117.86 (19)	C15—C14—H14	119.8
N1—C1—C6	122.80 (18)	C13—C14—H14	119.8
C2—C1—C6	119.33 (19)	C14—C15—C10	120.9 (2)
C3—C2—C1	120.1 (2)	C14—C15—H15	119.6
C3—C2—H2	120.0	C10—C15—H15	119.6
C1—C2—H2	120.0	O1—C16—C17	120.1 (2)
C2—C3—C4	121.0 (2)	O1—C16—C8	119.41 (19)
C2—C3—H3	119.5	C17—C16—C8	120.4 (2)
C4—C3—H3	119.5	C18—C17—C16	125.0 (2)
C5—C4—C3	120.4 (2)	C18—C17—H17	117.5
C5—C4—H4	119.8	C16—C17—H17	117.5
C3—C4—H4	119.8	C17—C18—C19	127.3 (2)
C4—C5—C6	120.5 (2)	C17—C18—H18	116.4
C4—C5—H5	119.7	C19—C18—H18	116.4
C6—C5—H5	119.7	C20—C19—C24	117.6 (2)
C5—C6—C1	118.67 (18)	C20—C19—C18	119.0 (2)
C5—C6—C7	123.60 (19)	C24—C19—C18	123.4 (2)
C1—C6—C7	117.71 (18)	C21—C20—C19	121.6 (2)
C8—C7—C6	118.19 (19)	C21—C20—H20	119.2
C8—C7—C10	121.31 (18)	C19—C20—H20	119.2
C6—C7—C10	120.49 (18)	C20—C21—C22	119.2 (2)
C7—C8—C9	120.04 (18)	C20—C21—H21	120.4
C7—C8—C16	119.47 (18)	C22—C21—H21	120.4
C9—C8—C16	120.24 (18)	C23—C22—C21	120.9 (2)
N1—C9—C8	122.44 (19)	C23—C22—Br1	119.93 (19)
N1—C9—C26	115.76 (19)	C21—C22—Br1	119.18 (19)
C8—C9—C26	121.80 (19)	C22—C23—C24	119.4 (2)
C15—C10—C11	118.4 (2)	C22—C23—H23	120.3
C15—C10—C7	120.84 (19)	C24—C23—H23	120.3
C11—C10—C7	120.77 (19)	C23—C24—C19	121.3 (2)
C12—C11—C10	120.1 (2)	C23—C24—H24	119.3
C12—C11—H11	119.9	C19—C24—H24	119.3
C10—C11—H11	119.9	C9—C26—H26A	109.5
C13—C12—C11	120.8 (2)	C9—C26—H26B	109.5
C13—C12—H12	119.6	H26A—C26—H26B	109.5
C11—C12—H12	119.6	C9—C26—H26C	109.5
C12—C13—C14	119.3 (2)	H26A—C26—H26C	109.5
C12—C13—H13	120.3	H26B—C26—H26C	109.5
C14—C13—H13	120.3
C9—N1—C1—C2	−178.4 (2)	C8—C7—C10—C11	114.2 (2)
C9—N1—C1—C6	0.4 (3)	C6—C7—C10—C11	−67.0 (3)
N1—C1—C2—C3	178.0 (2)	C15—C10—C11—C12	0.8 (3)
C6—C1—C2—C3	−0.7 (3)	C7—C10—C11—C12	−179.1 (2)
C1—C2—C3—C4	0.1 (4)	C10—C11—C12—C13	−0.2 (4)
C2—C3—C4—C5	0.5 (4)	C11—C12—C13—C14	−0.2 (4)
C3—C4—C5—C6	−0.5 (4)	C12—C13—C14—C15	−0.2 (4)
C4—C5—C6—C1	−0.2 (3)	C13—C14—C15—C10	0.9 (4)
C4—C5—C6—C7	−178.5 (2)	C11—C10—C15—C14	−1.2 (3)
N1—C1—C6—C5	−177.97 (19)	C7—C10—C15—C14	178.7 (2)
C2—C1—C6—C5	0.8 (3)	C7—C8—C16—O1	−66.9 (3)
N1—C1—C6—C7	0.5 (3)	C9—C8—C16—O1	107.3 (2)
C2—C1—C6—C7	179.20 (19)	C7—C8—C16—C17	112.9 (2)
C5—C6—C7—C8	177.32 (19)	C9—C8—C16—C17	−72.8 (3)
C1—C6—C7—C8	−1.0 (3)	O1—C16—C17—C18	173.7 (2)
C5—C6—C7—C10	−1.5 (3)	C8—C16—C17—C18	−6.1 (4)
C1—C6—C7—C10	−179.90 (18)	C16—C17—C18—C19	−179.4 (2)
C6—C7—C8—C9	0.8 (3)	C17—C18—C19—C20	−175.6 (2)
C10—C7—C8—C9	179.66 (18)	C17—C18—C19—C24	4.1 (4)
C6—C7—C8—C16	175.09 (18)	C24—C19—C20—C21	−0.6 (4)
C10—C7—C8—C16	−6.1 (3)	C18—C19—C20—C21	179.1 (2)
C1—N1—C9—C8	−0.6 (3)	C19—C20—C21—C22	0.2 (4)
C1—N1—C9—C26	−179.99 (19)	C20—C21—C22—C23	0.1 (4)
C7—C8—C9—N1	0.0 (3)	C20—C21—C22—Br1	−178.94 (19)
C16—C8—C9—N1	−174.19 (19)	C21—C22—C23—C24	0.0 (4)
C7—C8—C9—C26	179.3 (2)	Br1—C22—C23—C24	179.02 (19)
C16—C8—C9—C26	5.1 (3)	C22—C23—C24—C19	−0.4 (4)
C8—C7—C10—C15	−65.7 (3)	C20—C19—C24—C23	0.7 (4)
C6—C7—C10—C15	113.1 (2)	C18—C19—C24—C23	−179.0 (2)