(2E)-3-(Biphenyl-4-yl)-1-(quinolin-2-yl)prop-2-en-1-one

Butcher, R.J.; Jasinski, J.P.; Narayana, B.; Mayekar, A.N.; Yathirajan, H.S.

doi:10.1107/S1600536807034721

(2E)-3-(Biphenyl-4-yl)-1-(quinolin-2-yl)prop-2-en-1-one

R. J. Butcher, J. P. Jasinski, B. Narayana, A. N. Mayekar and H. S. Yathirajan

In the title molecule, C₂₄H₁₇NO, the mean planes of the two aromatic rings of the biphenyl group make a dihedral angle of 45.0 (8)°. The mean plane of the quinolin-2-yl group makes angles of 18.2 (6) and 61.9 (8)° with the benzene rings closest to and farthest away from the prop-2-en-1-one group, and 7.4 (1)° with the plane of the prop-2-en-1-one group. The structure is stabilized by intermolecular C—H

O hydrogen-bond interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807034721/at2342sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807034721/at2342Isup2.hkl Contains datablock I

CCDC reference: 657801

checkCIF report

Key indicators

Single-crystal X-ray study
T = 203 K
Mean (C-C) = 0.002 Å
R factor = 0.047
wR factor = 0.148
Data-to-parameter ratio = 24.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.99
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C24 H17 N O

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 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
   0 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

Comment top

Chalcones have been reported to possess many useful properties, including anti-inflammatory, antimicrobial, antifungal, antioxidant, cytotoxic, antitumor and anticancer activities. Among several organic compounds reported for their non linear optical (NLO) property, chalcone derivatives are noticeable materials for their excellent blue light transmittance and good crystallizability. We have synthesized a new chalcone, (I), and herein report the crystal structure of (I) (Fig. 1).

Intermolecular C—H···O hydrogen bond interactions occur between C18—H18A and O, and stabilize the structure as indicated in the packing diagram (Fig. 2).

Related literature top

For related structures, see: Fischer et al. (2007a,b,c,d,e); Sarojini et al. (2007); Yathirajan et al. (2007). For related literature, see: Fichou et al. (1988); Sarojini et al. (2006).

Experimental top

5 ml of 40% KOH solution was added to a thoroughly stirred solution of 2-acetylquinoline (1.71 g, 0.01 mol) and 4-biphenylaldehyde (1.82 g, 0.01 mol) in 25 ml me thanol. The solution was stirred overnight and filtered. The product obtained was crystallized from acetone/toluene (1:1) mixture (m.p.: 419–421 K). Analysis for C₂₄H₁₇NO: Found (Calculated): C 85.83 (85.94), H 5.07(5.11), N 4.12% (4.18%).

Structure description top

Intermolecular C—H···O hydrogen bond interactions occur between C18—H18A and O, and stabilize the structure as indicated in the packing diagram (Fig. 2).

For related structures, see: Fischer et al. (2007a,b,c,d,e); Sarojini et al. (2007); Yathirajan et al. (2007). For related literature, see: Fichou et al. (1988); Sarojini et al. (2006).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. Molecular structure of the title compound (I), showing atom labeling and 50% probability displacement ellipsoids.
	Fig. 2. Packing diagram of (I) viewed down the b axis. Dashed lines indicate C–H···O hydrogen bonds.

(2E)-3-(Biphenyl-4-yl)-1-(quinolin-2-yl)prop-2-en-1-one top

Crystal data top

C₂₄H₁₇NO	Z = 2
M_r = 335.39	F(000) = 352
Triclinic, P1	D_x = 1.293 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.9808 (12) Å	Cell parameters from 5911 reflections
b = 11.9617 (18) Å	θ = 4.6–32.4°
c = 13.2239 (16) Å	µ = 0.08 mm⁻¹
α = 109.401 (12)°	T = 203 K
β = 92.981 (13)°	Plate, colourless
γ = 102.967 (15)°	0.57 × 0.43 × 0.19 mm
V = 861.3 (3) Å³

Data collection top

Oxford Diffraction Gemini R diffractometer	5643 independent reflections
Radiation source: fine-focus sealed tube	3561 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
Detector resolution: 10.5081 pixels mm^-1	θ_max = 32.5°, θ_min = 4.6°
φ and ω scans	h = −8→7
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)	k = −17→17
T_min = 0.922, T_max = 1.000	l = −19→17
12993 measured reflections

Refinement top

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.148	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0888P)²] where P = (F_o² + 2F_c²)/3
5643 reflections	(Δ/σ)_max = 0.001
235 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₂₄H₁₇NO	γ = 102.967 (15)°
M_r = 335.39	V = 861.3 (3) Å³
Triclinic, P1	Z = 2
a = 5.9808 (12) Å	Mo Kα radiation
b = 11.9617 (18) Å	µ = 0.08 mm⁻¹
c = 13.2239 (16) Å	T = 203 K
α = 109.401 (12)°	0.57 × 0.43 × 0.19 mm
β = 92.981 (13)°

Data collection top

Oxford Diffraction Gemini R diffractometer	5643 independent reflections
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)	3561 reflections with I > 2σ(I)
T_min = 0.922, T_max = 1.000	R_int = 0.023
12993 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.148	H-atom parameters constrained
S = 1.04	Δρ_max = 0.28 e Å⁻³
5643 reflections	Δρ_min = −0.30 e Å⁻³
235 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
O	−0.19597 (14)	0.61552 (7)	0.49028 (7)	0.0421 (2)
N	0.24910 (15)	0.59911 (7)	0.32703 (7)	0.0276 (2)
C1	0.14418 (18)	0.64559 (9)	0.41063 (8)	0.0258 (2)
C2	0.2344 (2)	0.76334 (9)	0.49132 (9)	0.0325 (2)
H2A	0.1537	0.7920	0.5497	0.039*
C3	0.4399 (2)	0.83407 (10)	0.48259 (9)	0.0353 (3)
H3A	0.5034	0.9119	0.5357	0.042*
C4	0.55752 (19)	0.79045 (9)	0.39372 (9)	0.0315 (2)
C5	0.7716 (2)	0.85790 (11)	0.37748 (11)	0.0417 (3)
H5A	0.8394	0.9377	0.4265	0.050*
C6	0.8798 (2)	0.80849 (12)	0.29189 (11)	0.0440 (3)
H6A	1.0218	0.8543	0.2825	0.053*
C7	0.7806 (2)	0.68917 (11)	0.21717 (10)	0.0399 (3)
H7A	0.8573	0.6558	0.1586	0.048*
C8	0.5735 (2)	0.62167 (11)	0.22940 (9)	0.0345 (3)
H8A	0.5086	0.5424	0.1789	0.041*
C9	0.45601 (18)	0.67022 (9)	0.31745 (8)	0.0279 (2)
C10	−0.08621 (19)	0.56987 (9)	0.41909 (8)	0.0279 (2)
C11	−0.17124 (19)	0.44328 (9)	0.34193 (8)	0.0283 (2)
H11A	−0.0762	0.4093	0.2923	0.034*
C12	−0.38345 (18)	0.37616 (9)	0.34197 (8)	0.0272 (2)
H12A	−0.4748	0.4151	0.3908	0.033*
C13	−0.48699 (17)	0.24784 (9)	0.27318 (8)	0.0245 (2)
C14	−0.36185 (18)	0.17609 (9)	0.20453 (9)	0.0305 (2)
H14A	−0.2070	0.2110	0.2001	0.037*
C15	−0.46337 (18)	0.05480 (9)	0.14335 (9)	0.0307 (2)
H15A	−0.3751	0.0082	0.0987	0.037*
C16	−0.69470 (17)	−0.00094 (8)	0.14600 (8)	0.0248 (2)
C17	−0.82021 (18)	0.07111 (9)	0.21369 (8)	0.0276 (2)
H17A	−0.9764	0.0368	0.2165	0.033*
C18	−0.71725 (18)	0.19243 (9)	0.27675 (8)	0.0288 (2)
H18A	−0.8041	0.2385	0.3229	0.035*
C19	−0.79925 (18)	−0.13074 (9)	0.07668 (8)	0.0258 (2)
C20	−0.6782 (2)	−0.22039 (9)	0.06761 (9)	0.0330 (2)
H20A	−0.5313	−0.1987	0.1082	0.040*
C21	−0.7720 (2)	−0.34030 (10)	−0.00032 (10)	0.0381 (3)
H21A	−0.6892	−0.3995	−0.0047	0.046*
C22	−0.9867 (2)	−0.37409 (10)	−0.06192 (9)	0.0368 (3)
H22A	−1.0477	−0.4553	−0.1095	0.044*
C23	−1.1119 (2)	−0.28698 (10)	−0.05302 (9)	0.0344 (2)
H23A	−1.2593	−0.3095	−0.0933	0.041*
C24	−1.01799 (19)	−0.16680 (9)	0.01560 (9)	0.0304 (2)
H24A	−1.1032	−0.1083	0.0212	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O	0.0385 (5)	0.0370 (4)	0.0374 (5)	0.0026 (4)	0.0143 (4)	−0.0006 (4)
N	0.0268 (5)	0.0251 (4)	0.0284 (4)	0.0029 (4)	0.0031 (3)	0.0090 (3)
C1	0.0279 (5)	0.0221 (5)	0.0249 (5)	0.0036 (4)	0.0000 (4)	0.0077 (4)
C2	0.0395 (6)	0.0263 (5)	0.0265 (5)	0.0051 (5)	0.0028 (4)	0.0050 (4)
C3	0.0388 (6)	0.0238 (5)	0.0345 (6)	−0.0006 (5)	−0.0040 (5)	0.0059 (4)
C4	0.0299 (6)	0.0278 (5)	0.0349 (6)	0.0022 (4)	−0.0028 (4)	0.0132 (4)
C5	0.0358 (7)	0.0335 (6)	0.0503 (7)	−0.0036 (5)	−0.0038 (5)	0.0172 (5)
C6	0.0304 (6)	0.0491 (7)	0.0580 (8)	0.0000 (5)	0.0037 (6)	0.0328 (6)
C7	0.0344 (6)	0.0506 (7)	0.0440 (7)	0.0121 (5)	0.0113 (5)	0.0269 (6)
C8	0.0342 (6)	0.0367 (6)	0.0339 (6)	0.0085 (5)	0.0056 (5)	0.0143 (5)
C9	0.0265 (5)	0.0272 (5)	0.0302 (5)	0.0030 (4)	0.0008 (4)	0.0134 (4)
C10	0.0294 (5)	0.0258 (5)	0.0259 (5)	0.0042 (4)	0.0039 (4)	0.0074 (4)
C11	0.0309 (6)	0.0249 (5)	0.0259 (5)	0.0049 (4)	0.0064 (4)	0.0060 (4)
C12	0.0286 (5)	0.0256 (5)	0.0246 (5)	0.0056 (4)	0.0050 (4)	0.0061 (4)
C13	0.0238 (5)	0.0241 (4)	0.0251 (5)	0.0057 (4)	0.0039 (4)	0.0081 (4)
C14	0.0223 (5)	0.0297 (5)	0.0345 (6)	0.0037 (4)	0.0070 (4)	0.0062 (4)
C15	0.0253 (5)	0.0281 (5)	0.0349 (5)	0.0080 (4)	0.0102 (4)	0.0048 (4)
C16	0.0247 (5)	0.0221 (4)	0.0266 (5)	0.0047 (4)	0.0048 (4)	0.0082 (4)
C17	0.0222 (5)	0.0262 (5)	0.0311 (5)	0.0040 (4)	0.0069 (4)	0.0069 (4)
C18	0.0261 (5)	0.0278 (5)	0.0300 (5)	0.0085 (4)	0.0085 (4)	0.0051 (4)
C19	0.0251 (5)	0.0240 (5)	0.0270 (5)	0.0046 (4)	0.0063 (4)	0.0079 (4)
C20	0.0295 (6)	0.0280 (5)	0.0402 (6)	0.0076 (4)	0.0029 (5)	0.0104 (5)
C21	0.0422 (7)	0.0265 (5)	0.0442 (7)	0.0107 (5)	0.0092 (5)	0.0088 (5)
C22	0.0457 (7)	0.0244 (5)	0.0325 (6)	0.0013 (5)	0.0065 (5)	0.0049 (4)
C23	0.0317 (6)	0.0328 (5)	0.0321 (6)	−0.0004 (5)	0.0012 (4)	0.0093 (4)
C24	0.0293 (6)	0.0285 (5)	0.0328 (5)	0.0073 (4)	0.0052 (4)	0.0100 (4)

Geometric parameters (Å, º) top

O—C10	1.2243 (13)	C12—H12A	0.9400
N—C1	1.3211 (13)	C13—C18	1.3985 (14)
N—C9	1.3735 (13)	C13—C14	1.4008 (14)
C1—C2	1.4192 (14)	C14—C15	1.3791 (15)
C1—C10	1.5016 (15)	C14—H14A	0.9400
C2—C3	1.3612 (16)	C15—C16	1.4024 (14)
C2—H2A	0.9400	C15—H15A	0.9400
C3—C4	1.4113 (17)	C16—C17	1.3983 (14)
C3—H3A	0.9400	C16—C19	1.4836 (14)
C4—C5	1.4200 (16)	C17—C18	1.3865 (14)
C4—C9	1.4265 (15)	C17—H17A	0.9400
C5—C6	1.3613 (19)	C18—H18A	0.9400
C5—H5A	0.9400	C19—C24	1.3983 (15)
C6—C7	1.4098 (18)	C19—C20	1.4003 (14)
C6—H6A	0.9400	C20—C21	1.3819 (15)
C7—C8	1.3676 (16)	C20—H20A	0.9400
C7—H7A	0.9400	C21—C22	1.3842 (17)
C8—C9	1.4165 (15)	C21—H21A	0.9400
C8—H8A	0.9400	C22—C23	1.3918 (17)
C10—C11	1.4719 (14)	C22—H22A	0.9400
C11—C12	1.3410 (14)	C23—C24	1.3869 (15)
C11—H11A	0.9400	C23—H23A	0.9400
C12—C13	1.4677 (14)	C24—H24A	0.9400

C1—N—C9	117.67 (9)	C18—C13—C14	117.74 (9)
N—C1—C2	123.87 (10)	C18—C13—C12	119.83 (9)
N—C1—C10	117.76 (9)	C14—C13—C12	122.41 (9)
C2—C1—C10	118.36 (9)	C15—C14—C13	120.71 (10)
C3—C2—C1	118.77 (10)	C15—C14—H14A	119.6
C3—C2—H2A	120.6	C13—C14—H14A	119.6
C1—C2—H2A	120.6	C14—C15—C16	121.78 (9)
C2—C3—C4	119.95 (10)	C14—C15—H15A	119.1
C2—C3—H3A	120.0	C16—C15—H15A	119.1
C4—C3—H3A	120.0	C17—C16—C15	117.47 (9)
C3—C4—C5	123.93 (10)	C17—C16—C19	122.43 (9)
C3—C4—C9	117.45 (10)	C15—C16—C19	120.08 (9)
C5—C4—C9	118.61 (11)	C18—C17—C16	120.84 (9)
C6—C5—C4	120.86 (11)	C18—C17—H17A	119.6
C6—C5—H5A	119.6	C16—C17—H17A	119.6
C4—C5—H5A	119.6	C17—C18—C13	121.44 (9)
C5—C6—C7	120.50 (11)	C17—C18—H18A	119.3
C5—C6—H6A	119.8	C13—C18—H18A	119.3
C7—C6—H6A	119.8	C24—C19—C20	117.87 (9)
C8—C7—C6	120.43 (11)	C24—C19—C16	121.22 (9)
C8—C7—H7A	119.8	C20—C19—C16	120.88 (9)
C6—C7—H7A	119.8	C21—C20—C19	120.80 (10)
C7—C8—C9	120.60 (11)	C21—C20—H20A	119.6
C7—C8—H8A	119.7	C19—C20—H20A	119.6
C9—C8—H8A	119.7	C20—C21—C22	120.66 (10)
N—C9—C8	118.72 (10)	C20—C21—H21A	119.7
N—C9—C4	122.27 (10)	C22—C21—H21A	119.7
C8—C9—C4	119.01 (10)	C21—C22—C23	119.56 (10)
O—C10—C11	122.40 (10)	C21—C22—H22A	120.2
O—C10—C1	118.77 (9)	C23—C22—H22A	120.2
C11—C10—C1	118.83 (9)	C24—C23—C22	119.70 (11)
C12—C11—C10	120.39 (9)	C24—C23—H23A	120.2
C12—C11—H11A	119.8	C22—C23—H23A	120.2
C10—C11—H11A	119.8	C23—C24—C19	121.39 (10)
C11—C12—C13	126.36 (9)	C23—C24—H24A	119.3
C11—C12—H12A	116.8	C19—C24—H24A	119.3
C13—C12—H12A	116.8

C9—N—C1—C2	−0.94 (15)	C10—C11—C12—C13	−177.31 (9)
C9—N—C1—C10	177.83 (8)	C11—C12—C13—C18	−175.30 (10)
N—C1—C2—C3	0.65 (16)	C11—C12—C13—C14	6.16 (16)
C10—C1—C2—C3	−178.11 (9)	C18—C13—C14—C15	−0.39 (15)
C1—C2—C3—C4	0.80 (16)	C12—C13—C14—C15	178.18 (10)
C2—C3—C4—C5	179.59 (10)	C13—C14—C15—C16	0.90 (16)
C2—C3—C4—C9	−1.80 (15)	C14—C15—C16—C17	−0.21 (15)
C3—C4—C5—C6	177.65 (11)	C14—C15—C16—C19	178.34 (9)
C9—C4—C5—C6	−0.95 (16)	C15—C16—C17—C18	−0.98 (14)
C4—C5—C6—C7	0.30 (18)	C19—C16—C17—C18	−179.49 (9)
C5—C6—C7—C8	0.33 (17)	C16—C17—C18—C13	1.51 (16)
C6—C7—C8—C9	−0.28 (16)	C14—C13—C18—C17	−0.80 (15)
C1—N—C9—C8	179.06 (9)	C12—C13—C18—C17	−179.40 (9)
C1—N—C9—C4	−0.18 (14)	C17—C16—C19—C24	44.88 (14)
C7—C8—C9—N	−179.65 (9)	C15—C16—C19—C24	−133.59 (10)
C7—C8—C9—C4	−0.38 (15)	C17—C16—C19—C20	−137.29 (11)
C3—C4—C9—N	1.53 (15)	C15—C16—C19—C20	44.24 (14)
C5—C4—C9—N	−179.78 (9)	C24—C19—C20—C21	0.50 (15)
C3—C4—C9—C8	−177.71 (9)	C16—C19—C20—C21	−177.40 (10)
C5—C4—C9—C8	0.98 (15)	C19—C20—C21—C22	0.79 (17)
N—C1—C10—O	−173.47 (9)	C20—C21—C22—C23	−1.76 (18)
C2—C1—C10—O	5.37 (15)	C21—C22—C23—C24	1.41 (17)
N—C1—C10—C11	6.87 (14)	C22—C23—C24—C19	−0.11 (16)
C2—C1—C10—C11	−174.29 (9)	C20—C19—C24—C23	−0.84 (15)
O—C10—C11—C12	5.32 (16)	C16—C19—C24—C23	177.06 (9)
C1—C10—C11—C12	−175.04 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18A···Oⁱ	0.94	2.51	3.3222 (13)	145

Symmetry code: (i) −x−1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₄H₁₇NO
M_r	335.39
Crystal system, space group	Triclinic, P1
Temperature (K)	203
a, b, c (Å)	5.9808 (12), 11.9617 (18), 13.2239 (16)
α, β, γ (°)	109.401 (12), 92.981 (13), 102.967 (15)
V (Å³)	861.3 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.57 × 0.43 × 0.19

Data collection
Diffractometer	Oxford Diffraction Gemini R
Absorption correction	Multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)
T_min, T_max	0.922, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	12993, 5643, 3561
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.756

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.148, 1.04
No. of reflections	5643
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.30

Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), CrysAlis PRO, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18A···Oⁱ	0.94	2.51	3.3222 (13)	145.1

Symmetry code: (i) −x−1, −y+1, −z+1.

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