3-(4-Chloro-phen-yl)-1-(2-methyl-4-phenyl-quinolin-3-yl)prop-2-en-1-one.

The crystal structure of the title compound, C(25)H(18)ClNO, shows that the mol-ecules are isolated and not involved in inter-molecular C-H⋯O or C-H⋯Cl inter-actions. However, the phenyl and quinoline rings are involved in π-π inter-actions [centroid-centroid distance = 3.8829 (9) Å].

Related literature

For background details and the biological activity of quinolines, see: Markees et al. (1970 ▶); Campbell et al. (1998 ▶); Bhat et al. (2005 ▶). For the biological activity of chalcones, see: Wu et al. (2006 ▶).

Experimental

Crystal data

C25H18ClNO

M = 383.85

Triclinic,

a = 6.5376 (2) Å

b = 10.0345 (4) Å

c = 15.6545 (6) Å

α = 90.845 (3)°

β = 95.521 (3)°

γ = 107.035 (3)°

V = 976.36 (6) Å3

Z = 2

Cu Kα radiation

μ = 1.84 mm−1

T = 295 K

0.52 × 0.18 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.544, T max = 1.000

7607 measured reflections

4065 independent reflections

3402 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.160

S = 1.04

4065 reflections

254 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.24 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811004661/ez2231sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811004661/ez2231Isup2.hkl

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

C25H18ClNO	Z = 2
Mr = 383.85	F(000) = 400
Triclinic, P1	Dx = 1.306 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 6.5376 (2) Å	Cell parameters from 4929 reflections
b = 10.0345 (4) Å	θ = 5.3–77.1°
c = 15.6545 (6) Å	µ = 1.84 mm−1
α = 90.845 (3)°	T = 295 K
β = 95.521 (3)°	Needle, colorless
γ = 107.035 (3)°	0.52 × 0.18 × 0.12 mm
V = 976.36 (6) Å3

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	4065 independent reflections
Radiation source: Enhance (Cu) X-ray Source	3402 reflections with I > 2σ(I)
graphite	Rint = 0.019
Detector resolution: 10.5081 pixels mm-1	θmax = 77.4°, θmin = 5.3°
ω scans	h = −3→8
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −12→12
Tmin = 0.544, Tmax = 1.000	l = −19→19
7607 measured reflections

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.160	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.1125P)2 + 0.0628P] where P = (Fo2 + 2Fc2)/3
4065 reflections	(Δ/σ)max = 0.001
254 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

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
Cl	−0.41045 (10)	−0.24622 (7)	0.99317 (4)	0.1004 (3)
O	0.6524 (2)	0.15628 (12)	0.65464 (9)	0.0678 (3)
N	0.22876 (19)	0.41447 (12)	0.55076 (8)	0.0485 (3)
C1	0.0479 (2)	0.02060 (15)	0.82219 (9)	0.0505 (3)
C2	0.0750 (3)	−0.10510 (17)	0.85056 (12)	0.0603 (4)
H2A	0.1889	−0.1338	0.8340	0.072*
C3	−0.0651 (3)	−0.18756 (18)	0.90290 (12)	0.0671 (4)
H3A	−0.0465	−0.2714	0.9212	0.081*
C4	−0.2326 (3)	−0.14364 (19)	0.92754 (11)	0.0638 (4)
C5	−0.2633 (3)	−0.0196 (2)	0.90095 (13)	0.0696 (4)
H5A	−0.3765	0.0092	0.9181	0.083*
C6	−0.1218 (3)	0.06090 (18)	0.84822 (12)	0.0620 (4)
H6A	−0.1416	0.1444	0.8299	0.074*
C7	0.1907 (3)	0.11066 (14)	0.76588 (10)	0.0515 (3)
H7A	0.1646	0.1949	0.7532	0.062*
C8	0.3530 (3)	0.08465 (14)	0.73113 (10)	0.0543 (4)
H8A	0.3797	0.0001	0.7420	0.065*
C9	0.4934 (2)	0.18093 (14)	0.67652 (10)	0.0488 (3)
C10	0.4416 (2)	0.31192 (13)	0.64783 (8)	0.0434 (3)
C11	0.2682 (2)	0.30333 (14)	0.58322 (9)	0.0463 (3)
C12	0.1198 (3)	0.16483 (16)	0.54764 (11)	0.0588 (4)
H12A	0.0640	0.1744	0.4898	0.088*
H12B	0.0030	0.1345	0.5824	0.088*
H12C	0.1978	0.0973	0.5480	0.088*
C13	0.3573 (2)	0.54308 (14)	0.58070 (8)	0.0447 (3)
C14	0.3076 (3)	0.66120 (16)	0.54642 (10)	0.0547 (4)
H14A	0.1939	0.6494	0.5037	0.066*
C15	0.4265 (3)	0.79222 (17)	0.57609 (12)	0.0622 (4)
H15A	0.3928	0.8693	0.5535	0.075*
C16	0.5992 (3)	0.81211 (15)	0.64035 (12)	0.0596 (4)
H16A	0.6782	0.9020	0.6602	0.072*
C17	0.6522 (3)	0.70013 (15)	0.67399 (10)	0.0511 (3)
H17A	0.7675	0.7145	0.7162	0.061*
C18	0.5324 (2)	0.56215 (13)	0.64491 (8)	0.0422 (3)
C19	0.5751 (2)	0.44052 (13)	0.67829 (8)	0.0414 (3)
C20	0.7569 (2)	0.45328 (13)	0.74642 (8)	0.0437 (3)
C21	0.9681 (3)	0.50871 (19)	0.72893 (11)	0.0599 (4)
H21A	0.9977	0.5393	0.6744	0.072*
C22	1.1357 (3)	0.5186 (2)	0.79260 (14)	0.0710 (5)
H22A	1.2772	0.5567	0.7807	0.085*
C23	1.0937 (3)	0.4725 (2)	0.87317 (12)	0.0673 (5)
H23A	1.2066	0.4777	0.9153	0.081*
C24	0.8847 (3)	0.41878 (18)	0.89139 (11)	0.0623 (4)
H24A	0.8563	0.3886	0.9461	0.075*
C25	0.7164 (2)	0.40945 (15)	0.82857 (9)	0.0512 (3)
H25A	0.5753	0.3736	0.8414	0.061*

	U11	U22	U33	U12	U13	U23
Cl	0.0863 (4)	0.1060 (5)	0.0916 (4)	−0.0055 (3)	0.0264 (3)	0.0365 (3)
O	0.0731 (7)	0.0532 (6)	0.0893 (8)	0.0308 (6)	0.0285 (6)	0.0164 (6)
N	0.0481 (6)	0.0462 (6)	0.0503 (6)	0.0133 (5)	0.0028 (5)	0.0012 (5)
C1	0.0537 (8)	0.0416 (7)	0.0515 (7)	0.0073 (6)	0.0036 (6)	0.0039 (5)
C2	0.0624 (9)	0.0487 (8)	0.0697 (10)	0.0146 (7)	0.0107 (7)	0.0116 (7)
C3	0.0731 (11)	0.0506 (8)	0.0718 (10)	0.0093 (7)	0.0057 (8)	0.0178 (7)
C4	0.0599 (9)	0.0639 (9)	0.0542 (8)	−0.0025 (7)	0.0051 (7)	0.0109 (7)
C5	0.0627 (10)	0.0746 (11)	0.0719 (11)	0.0178 (8)	0.0168 (8)	0.0097 (8)
C6	0.0667 (10)	0.0536 (8)	0.0677 (9)	0.0189 (7)	0.0126 (7)	0.0111 (7)
C7	0.0600 (8)	0.0358 (6)	0.0576 (8)	0.0121 (6)	0.0061 (6)	0.0067 (5)
C8	0.0636 (9)	0.0368 (6)	0.0634 (8)	0.0146 (6)	0.0107 (7)	0.0104 (6)
C9	0.0551 (8)	0.0377 (6)	0.0540 (7)	0.0135 (6)	0.0082 (6)	0.0043 (5)
C10	0.0478 (7)	0.0374 (6)	0.0460 (6)	0.0120 (5)	0.0112 (5)	0.0043 (5)
C11	0.0475 (7)	0.0404 (6)	0.0497 (7)	0.0102 (5)	0.0079 (5)	−0.0003 (5)
C12	0.0581 (8)	0.0442 (7)	0.0668 (9)	0.0065 (6)	−0.0008 (7)	−0.0035 (6)
C13	0.0488 (7)	0.0419 (6)	0.0454 (6)	0.0152 (5)	0.0093 (5)	0.0047 (5)
C14	0.0580 (8)	0.0511 (8)	0.0578 (8)	0.0214 (6)	0.0024 (6)	0.0100 (6)
C15	0.0742 (10)	0.0447 (7)	0.0734 (10)	0.0255 (7)	0.0080 (8)	0.0132 (7)
C16	0.0712 (10)	0.0368 (7)	0.0684 (9)	0.0124 (6)	0.0065 (7)	0.0008 (6)
C17	0.0579 (8)	0.0413 (7)	0.0522 (7)	0.0121 (6)	0.0040 (6)	0.0016 (5)
C18	0.0492 (7)	0.0374 (6)	0.0411 (6)	0.0127 (5)	0.0099 (5)	0.0036 (5)
C19	0.0466 (6)	0.0390 (6)	0.0403 (6)	0.0134 (5)	0.0099 (5)	0.0039 (5)
C20	0.0491 (7)	0.0386 (6)	0.0454 (6)	0.0153 (5)	0.0068 (5)	0.0021 (5)
C21	0.0529 (8)	0.0722 (10)	0.0563 (8)	0.0185 (7)	0.0134 (6)	0.0028 (7)
C22	0.0461 (8)	0.0879 (13)	0.0803 (12)	0.0219 (8)	0.0073 (8)	−0.0080 (9)
C23	0.0642 (10)	0.0716 (10)	0.0683 (10)	0.0301 (8)	−0.0129 (8)	−0.0077 (8)
C24	0.0742 (10)	0.0602 (9)	0.0508 (8)	0.0198 (8)	−0.0021 (7)	0.0065 (6)
C25	0.0544 (8)	0.0476 (7)	0.0488 (7)	0.0108 (6)	0.0058 (6)	0.0060 (5)

Cl—C4	1.7399 (17)	C12—H12C	0.9600
O—C9	1.2149 (19)	C13—C18	1.4149 (19)
N—C11	1.3147 (18)	C13—C14	1.4173 (19)
N—C13	1.3646 (18)	C14—C15	1.365 (2)
C1—C6	1.380 (2)	C14—H14A	0.9300
C1—C2	1.397 (2)	C15—C16	1.403 (2)
C1—C7	1.467 (2)	C15—H15A	0.9300
C2—C3	1.384 (2)	C16—C17	1.367 (2)
C2—H2A	0.9300	C16—H16A	0.9300
C3—C4	1.379 (3)	C17—C18	1.4196 (19)
C3—H3A	0.9300	C17—H17A	0.9300
C4—C5	1.381 (3)	C18—C19	1.4253 (17)
C5—C6	1.385 (2)	C19—C20	1.4929 (18)
C5—H5A	0.9300	C20—C21	1.385 (2)
C6—H6A	0.9300	C20—C25	1.390 (2)
C7—C8	1.326 (2)	C21—C22	1.388 (2)
C7—H7A	0.9300	C21—H21A	0.9300
C8—C9	1.471 (2)	C22—C23	1.375 (3)
C8—H8A	0.9300	C22—H22A	0.9300
C9—C10	1.5142 (18)	C23—C24	1.374 (3)
C10—C19	1.3770 (18)	C23—H23A	0.9300
C10—C11	1.4267 (19)	C24—C25	1.384 (2)
C11—C12	1.5053 (19)	C24—H24A	0.9300
C12—H12A	0.9600	C25—H25A	0.9300
C12—H12B	0.9600
C11—N—C13	118.73 (12)	N—C13—C18	122.82 (12)
C6—C1—C2	118.20 (15)	N—C13—C14	117.62 (13)
C6—C1—C7	118.85 (14)	C18—C13—C14	119.55 (13)
C2—C1—C7	122.95 (14)	C15—C14—C13	120.05 (14)
C3—C2—C1	120.99 (16)	C15—C14—H14A	120.0
C3—C2—H2A	119.5	C13—C14—H14A	120.0
C1—C2—H2A	119.5	C14—C15—C16	120.79 (14)
C4—C3—C2	119.06 (16)	C14—C15—H15A	119.6
C4—C3—H3A	120.5	C16—C15—H15A	119.6
C2—C3—H3A	120.5	C17—C16—C15	120.43 (14)
C3—C4—C5	121.40 (16)	C17—C16—H16A	119.8
C3—C4—Cl	119.65 (14)	C15—C16—H16A	119.8
C5—C4—Cl	118.96 (15)	C16—C17—C18	120.51 (14)
C4—C5—C6	118.56 (17)	C16—C17—H17A	119.7
C4—C5—H5A	120.7	C18—C17—H17A	119.7
C6—C5—H5A	120.7	C13—C18—C17	118.66 (12)
C1—C6—C5	121.79 (16)	C13—C18—C19	117.70 (12)
C1—C6—H6A	119.1	C17—C18—C19	123.63 (13)
C5—C6—H6A	119.1	C10—C19—C18	118.40 (12)
C8—C7—C1	126.86 (13)	C10—C19—C20	121.16 (12)
C8—C7—H7A	116.6	C18—C19—C20	120.42 (11)
C1—C7—H7A	116.6	C21—C20—C25	118.93 (14)
C7—C8—C9	124.21 (13)	C21—C20—C19	120.71 (13)
C7—C8—H8A	117.9	C25—C20—C19	120.37 (13)
C9—C8—H8A	117.9	C20—C21—C22	120.14 (16)
O—C9—C8	120.17 (13)	C20—C21—H21A	119.9
O—C9—C10	119.62 (13)	C22—C21—H21A	119.9
C8—C9—C10	120.21 (12)	C23—C22—C21	120.37 (16)
C19—C10—C11	119.78 (12)	C23—C22—H22A	119.8
C19—C10—C9	119.63 (12)	C21—C22—H22A	119.8
C11—C10—C9	120.30 (12)	C24—C23—C22	119.90 (16)
N—C11—C10	122.56 (12)	C24—C23—H23A	120.1
N—C11—C12	116.00 (13)	C22—C23—H23A	120.1
C10—C11—C12	121.44 (13)	C23—C24—C25	120.18 (16)
C11—C12—H12A	109.5	C23—C24—H24A	119.9
C11—C12—H12B	109.5	C25—C24—H24A	119.9
H12A—C12—H12B	109.5	C24—C25—C20	120.47 (15)
C11—C12—H12C	109.5	C24—C25—H25A	119.8
H12A—C12—H12C	109.5	C20—C25—H25A	119.8
H12B—C12—H12C	109.5
C6—C1—C2—C3	0.4 (3)	C13—C14—C15—C16	0.2 (3)
C7—C1—C2—C3	−179.28 (15)	C14—C15—C16—C17	0.4 (3)
C1—C2—C3—C4	−0.5 (3)	C15—C16—C17—C18	−0.5 (3)
C2—C3—C4—C5	0.1 (3)	N—C13—C18—C17	−177.84 (13)
C2—C3—C4—Cl	179.88 (13)	C14—C13—C18—C17	0.8 (2)
C3—C4—C5—C6	0.2 (3)	N—C13—C18—C19	0.69 (19)
Cl—C4—C5—C6	−179.55 (14)	C14—C13—C18—C19	179.30 (12)
C2—C1—C6—C5	−0.1 (3)	C16—C17—C18—C13	−0.1 (2)
C7—C1—C6—C5	179.63 (16)	C16—C17—C18—C19	−178.57 (13)
C4—C5—C6—C1	−0.2 (3)	C11—C10—C19—C18	1.17 (19)
C6—C1—C7—C8	−176.02 (16)	C9—C10—C19—C18	174.99 (11)
C2—C1—C7—C8	3.7 (3)	C11—C10—C19—C20	179.45 (11)
C1—C7—C8—C9	−178.63 (14)	C9—C10—C19—C20	−6.74 (19)
C7—C8—C9—O	172.12 (16)	C13—C18—C19—C10	−1.45 (18)
C7—C8—C9—C10	−7.4 (2)	C17—C18—C19—C10	177.00 (13)
O—C9—C10—C19	−67.03 (19)	C13—C18—C19—C20	−179.74 (11)
C8—C9—C10—C19	112.49 (15)	C17—C18—C19—C20	−1.3 (2)
O—C9—C10—C11	106.75 (17)	C10—C19—C20—C21	114.65 (16)
C8—C9—C10—C11	−73.73 (18)	C18—C19—C20—C21	−67.11 (18)
C13—N—C11—C10	−0.7 (2)	C10—C19—C20—C25	−65.29 (17)
C13—N—C11—C12	179.73 (13)	C18—C19—C20—C25	112.95 (15)
C19—C10—C11—N	−0.1 (2)	C25—C20—C21—C22	0.6 (2)
C9—C10—C11—N	−173.84 (13)	C19—C20—C21—C22	−179.32 (15)
C19—C10—C11—C12	179.44 (13)	C20—C21—C22—C23	0.6 (3)
C9—C10—C11—C12	5.7 (2)	C21—C22—C23—C24	−1.3 (3)
C11—N—C13—C18	0.4 (2)	C22—C23—C24—C25	0.8 (3)
C11—N—C13—C14	−178.23 (13)	C23—C24—C25—C20	0.5 (2)
N—C13—C14—C15	177.86 (15)	C21—C20—C25—C24	−1.2 (2)
C18—C13—C14—C15	−0.8 (2)	C19—C20—C25—C24	178.80 (13)