Second monoclinic form of (E)-3-(4-fluoro­phen­yl)-1-phenyl­prop-2-en-1-one

Arias-Ruiz, S.N.; Romero, N.; Lobato-García, C.E.; Gómez-Rivera, A.; Mendoza, A.

doi:10.1107/S1600536813028079

organic compounds

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ISSN: 2056-9890

Volume 69| Part 11| November 2013| Pages o1694-o1695

doi:10.1107/S1600536813028079

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Second monoclinic form of (E)-3-(4-fluorophenyl)-1-phenylprop-2-en-1-one

Saira N. Arias-Ruiz,^a Nancy Romero,^a Carlos E. Lobato-García,^a Abraham Gómez-Rivera ^a and Angel Mendoza ^b ^*

^aDivisión Académica de Ciencias Básicas, Universidad Juárez Autónoma de Tabasco, AP 24, 86690 Cunduacán, Tab., Mexico, and ^bCentro de Química, Instituto de Ciencias, Benemérita Universidad Autónoma de Puebla, 72570 Puebla, Pue., Mexico
^*Correspondence e-mail: angel.mendoza@correo.buap.mx

(Received 11 September 2013; accepted 12 October 2013; online 23 October 2013)

The unit-cell dimensions and space group of the second monoclinic polymorph of the title compound, C₁₅H₁₁FO, differ from those of the previously reported form [Jing (2009 ). Acta Cryst. E65, o2515]. The title compound shows an E conformation of the C=C bond with the 4-fluorophenyl group opposite to the benzoyl group. The torsion angle of between the planes of the 4-fluorophenyl and benzoyl groups is 10.53 (6)°. In the crystal, weak C—H⋯O and C—H⋯F interactions form a cross-linked packing motif, building sheets parallel to (-102).

CCDC reference: 966200

Related literature

For the first monoclinic polymorph of the title compound, see: Jing (2009). For related crystal structures, see: Li et al. (1992 ); Li & Su (1994 ); For biological properties reports of chalcones, see: Foresti et al. (2005 ); Nowakowska (2007 ); Kouskoura et al. (2008 ); Zhang et al. (2010 ); Doan & Tran (2011 ). For solvent-free synthesis of chalcones, see: Srivastava (2008 ); Krishnakumar & Swaminathan (2011 ); Thirunarayanan et al. (2012 ). For applications of chalcones in organic synthesis, see: Prakash et al. (2009 ); Bandgar et al. (2009 ).

Experimental

Crystal data

C₁₅H₁₁FO
M_r = 226.24
Monoclinic, P 2₁ /c
a = 8.6925 (4) Å
b = 5.9266 (2) Å
c = 22.6456 (9) Å
β = 95.423 (4)°
V = 1161.41 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.59 × 0.15 × 0.07 mm

Data collection

Oxford Diffraction Xcalibur (Atlas, Gemini) diffractometer
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.993, T_max = 0.999
22101 measured reflections
2276 independent reflections
1471 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.131
S = 1.01
2276 reflections
155 parameters
H-atom parameters constrained
Δρ_max = 0.11 e Å⁻³
Δρ_min = −0.11 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O1ⁱ	0.93	2.49	3.244 (2)	138
C13—H13⋯F1ⁱⁱ	0.93	2.68	3.465 (2)	142
Symmetry codes: (i) -x+1, -y, -z; (ii) $[x+1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: WinGX (Farrugia, 2012).

Supporting information

CCDC reference: 966200

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813028079/bh2484sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813028079/bh2484Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813028079/bh2484Isup3.cml

checkCIF report

Comment top

Chalcones, like the title compound, are highly interesting materials due to their antioxidant, antibacterial, antifungal, antitumor and anti-inflammatory properties (Zhang et al., 2010; Kouskoura et al., 2008; Nowakowska, 2007; Foresti et al., 2005 and Doan & Tran, 2011). The title compound was obtained by a green Claisen-Schimdt condensation of 4-fluorobenzaldehyde with acetophenone. This reaction was carried out by a free solvent and microwave assisted method, with p-toluenesulfonic acid as catalyst (Thirunarayanan et al., 2012; Krishnakumar & Swaminathan, 2011; Srivastava, 2008). Also, chalcones are valuable intermediates in organic synthesis because of the α,β-unsaturated carbonyl system, which is considered as a key building block (Prakash et al., 2009; Bandgar et al., 2009).

The crystal structure of the title compound, C₁₅H₁₁FO, has been reported previously at 93 K (Jing, 2009). However, here we report the structure of a second monoclinic polymorph, which was elucidated at 293 (2) K. The new polymorph crystallizes in space group P2₁/c, which is different from the previous space group, Cc. The cell parameters of the current monoclinic polymorph vary significantly from the earlier form [a = 24.926 (9), b = 5.6940 (19), c = 7.749 (3) Å and β = 94.747 (5)°]. Furthermore, two more halo-chalcones were reported previously: 4-bromochalcone [Li et al., 1992; unit-cell parameters: a = 29.027 (7), b = 7.26 (2), c = 5.917 (3) Å and β = 101.38 (3)°] and 4-chlorochalcone [Li & Su, 1994; unit-cell parameters: a = 8.211 (2), b = 5.869 (2), c = 25.291 (5) Å and β = 99.18 °]. Both compounds show similar cell parameters to current polymorphs of the F-chalcone, however the space group is P2₁/c for the Cl derivative and Cc for the Br-chalcone, both characterized at room temperature.

The title compound shows a configuration E on the C═C bond with p-fluorophenyl group opposite to the 1-phenylketone. Torsion angle of p-fluorophenyl to 1-phenylketone group is 10.53 (6)°. The crystal packing presents two intermolecular interactions of the type hydrogen bond (Table 1), C5—H5···O1 and C13—H13···F1 with the symmetry codes (i) -x + 1, -y, -z and (ii) x + 1, -y + 3/2, z + 1/2, respectively. These interactions form a cross-linked crystal packing, building sheets parallel to the (102) plane.

Related literature top

For the first monoclinic polymorph of the title compound, see: Jing (2009). For related crystal structures, see: Li et al. (1992); Li & Su (1994); For biological properties reports of chalcones, see: Foresti et al. (2005); Nowakowska (2007); Kouskoura et al. (2008); Zhang et al. (2010); Doan & Tran (2011). For solvent-free synthesis of chalcones, see: Srivastava (2008); Krishnakumar & Swaminathan (2011); Thirunarayanan et al. (2012). For applications of chalcones in organic synthesis, see: Prakash et al. (2009); Bandgar et al. (2009).

Experimental top

To a mixture of acetophenone (1.15 mmol) and 4-fluorobenzaldehyde (1.15 mmol) in dry media, 0.1 g of p-TsOH was added and the mixture was irradiated in a microwave oven at 480 W for 10 min. Completion of the reaction was tested by thin layer chromatography (TLC), and the crude product was purified by column chromatography on silica gel (eluent: hexane), to afford a yellow solid, (E)-3-(4-fluorophenyl)-1-phenylprop-2-en-1-one, in 85.4% yield, m. p. 79 °C. The pure product was recrystallized from hexane. The microwave oven VICHI: MW-600 (600 W) MOD: MICV/Vichy/F-814 was used; all the chemicals were purchased from Sigma-Aldrich and were used without further preparation. Spectroscopic analysis: ν_max/cm^-1 (neat KBr)= 3438, 1661, 1604, 1588, 1509, 1217, 1016, 829, 772. ¹H-NMR (400 MHz, CDCl₃): δ (p.p.m.) = 7.09 (tt, J= 2.0, 8.4 Hz, 2H), 7.46 (d, J=16 Hz, 1H), 7.49 (dd, J= 6.4, 8.4 Hz, 2H), 7.56 (dt, J=1.2, 6.4 Hz, 1H), 7.61 (ddt, J=2.0, 5.2, 8.4 Hz, 2H), 7.76 (d, J=16 Hz, 1H), 8.01 (dd, J=1.2, 8.4 Hz, 2H). ¹³C-NMR (101 MHz, CDCl₃): δ (p.p.m.) = 115.91, 116.13, 121.58, 128.38 (2 C), 128.56 (2 C), 130.22, 130.31, 132.77, 137.98, 143.38, 162.69, 165.19, 190.15.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top

Fig. 1. The molecular structure of title compound, with 30% probability displacement ellipsoids for non-H atoms.

(E)-3-(4-Fluorophenyl)-1-phenylprop-2-en-1-one top

Crystal data top

C₁₅H₁₁FO	F(000) = 472
M_r = 226.24	D_x = 1.294 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 352 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 8.6925 (4) Å	Cell parameters from 4193 reflections
b = 5.9266 (2) Å	θ = 3.6–23.2°
c = 22.6456 (9) Å	µ = 0.09 mm⁻¹
β = 95.423 (4)°	T = 293 K
V = 1161.41 (8) Å³	Prism, colourless
Z = 4	0.59 × 0.15 × 0.07 mm

Data collection top

Oxford Diffraction Xcalibur (Atlas, Gemini) diffractometer	2276 independent reflections
Graphite monochromator	1471 reflections with I > 2σ(I)
Detector resolution: 10.5564 pixels mm^-1	R_int = 0.044
ω scans	θ_max = 26.1°, θ_min = 2.8°
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009)	h = −10→10
T_min = 0.993, T_max = 0.999	k = −7→7
22101 measured reflections	l = −27→27

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.045	H-atom parameters constrained
wR(F²) = 0.131	w = 1/[σ²(F_o²) + (0.0624P)² + 0.1205P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
2276 reflections	Δρ_max = 0.11 e Å⁻³
155 parameters	Δρ_min = −0.11 e Å⁻³
0 restraints	Extinction correction: SHELXL2013
0 constraints	Extinction coefficient: 0.0047 (18)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₅H₁₁FO	V = 1161.41 (8) Å³
M_r = 226.24	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.6925 (4) Å	µ = 0.09 mm⁻¹
b = 5.9266 (2) Å	T = 293 K
c = 22.6456 (9) Å	0.59 × 0.15 × 0.07 mm
β = 95.423 (4)°

Data collection top

Oxford Diffraction Xcalibur (Atlas, Gemini) diffractometer	2276 independent reflections
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009)	1471 reflections with I > 2σ(I)
T_min = 0.993, T_max = 0.999	R_int = 0.044
22101 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.131	H-atom parameters constrained
S = 1.01	Δρ_max = 0.11 e Å⁻³
2276 reflections	Δρ_min = −0.11 e Å⁻³
155 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C2	0.48635 (19)	0.3169 (3)	0.11626 (7)	0.0677 (5)
H2	0.4743	0.4587	0.1328	0.081*
C4	0.31624 (17)	0.4186 (3)	0.02499 (7)	0.0603 (4)
O1	0.58960 (17)	−0.0451 (2)	0.13196 (6)	0.0977 (5)
C3	0.41537 (18)	0.2726 (3)	0.06357 (7)	0.0657 (4)
H3	0.4308	0.1283	0.0491	0.079*
C1	0.58376 (19)	0.1497 (3)	0.14973 (7)	0.0680 (5)
F1	0.02919 (14)	0.8135 (2)	−0.08612 (6)	0.1173 (5)
C10	0.67648 (18)	0.2155 (3)	0.20579 (7)	0.0620 (4)
C8	0.1728 (2)	0.7614 (3)	0.00570 (9)	0.0815 (5)
H8	0.1411	0.9022	0.018	0.098*
C5	0.2652 (2)	0.3477 (3)	−0.03154 (7)	0.0733 (5)
H5	0.2962	0.2074	−0.0445	0.088*
C9	0.2692 (2)	0.6298 (3)	0.04281 (8)	0.0735 (5)
H9	0.3034	0.6827	0.0804	0.088*
C7	0.1246 (2)	0.6831 (3)	−0.04919 (9)	0.0791 (5)
C6	0.1692 (2)	0.4803 (3)	−0.06940 (8)	0.0818 (6)
H6	0.1363	0.4317	−0.1076	0.098*
C15	0.7800 (2)	0.0620 (3)	0.23197 (9)	0.0910 (6)
H15	0.7907	−0.0775	0.214	0.109*
C11	0.6644 (2)	0.4203 (3)	0.23317 (8)	0.0818 (5)
H11	0.5962	0.5282	0.2162	0.098*
C13	0.8525 (2)	0.3131 (4)	0.31101 (8)	0.0909 (6)
H13	0.9105	0.3453	0.3466	0.109*
C12	0.7521 (3)	0.4682 (4)	0.28558 (9)	0.0928 (6)
H12	0.7425	0.6077	0.3037	0.111*
C14	0.8678 (3)	0.1097 (4)	0.28394 (10)	0.1066 (8)
H14	0.9376	0.0036	0.3007	0.128*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C2	0.0750 (11)	0.0601 (10)	0.0658 (10)	0.0067 (8)	−0.0043 (8)	−0.0066 (8)
C4	0.0562 (9)	0.0621 (9)	0.0614 (9)	−0.0056 (8)	−0.0005 (7)	−0.0005 (8)
O1	0.1263 (12)	0.0693 (8)	0.0905 (9)	0.0259 (7)	−0.0263 (8)	−0.0201 (7)
C3	0.0668 (10)	0.0602 (9)	0.0688 (10)	0.0014 (8)	−0.0003 (8)	−0.0053 (8)
C1	0.0740 (11)	0.0621 (10)	0.0665 (10)	0.0091 (8)	−0.0008 (8)	−0.0073 (8)
F1	0.1054 (9)	0.1264 (10)	0.1130 (9)	0.0174 (7)	−0.0265 (7)	0.0378 (8)
C10	0.0658 (10)	0.0610 (9)	0.0587 (9)	0.0044 (8)	0.0028 (7)	−0.0012 (7)
C8	0.0795 (12)	0.0741 (12)	0.0888 (13)	0.0132 (10)	−0.0026 (10)	0.0048 (10)
C5	0.0779 (11)	0.0716 (11)	0.0683 (11)	−0.0064 (9)	−0.0043 (9)	−0.0043 (9)
C9	0.0758 (11)	0.0729 (11)	0.0699 (11)	0.0071 (9)	−0.0032 (9)	−0.0054 (9)
C7	0.0642 (11)	0.0878 (13)	0.0824 (13)	−0.0012 (10)	−0.0073 (9)	0.0216 (11)
C6	0.0807 (12)	0.0935 (14)	0.0675 (11)	−0.0128 (11)	−0.0132 (9)	0.0056 (10)
C15	0.1073 (15)	0.0710 (11)	0.0887 (13)	0.0170 (11)	−0.0233 (11)	−0.0078 (10)
C11	0.0900 (13)	0.0775 (12)	0.0751 (11)	0.0183 (10)	−0.0077 (10)	−0.0150 (9)
C13	0.1022 (15)	0.1003 (15)	0.0659 (11)	−0.0081 (13)	−0.0140 (10)	−0.0003 (11)
C12	0.1098 (16)	0.0867 (13)	0.0791 (13)	0.0040 (12)	−0.0051 (12)	−0.0251 (11)
C14	0.1241 (18)	0.0903 (14)	0.0954 (15)	0.0148 (13)	−0.0433 (13)	−0.0021 (12)

Geometric parameters (Å, º) top

C2—C3	1.317 (2)	C5—C6	1.383 (2)
C2—C1	1.467 (2)	C5—H5	0.93
C2—H2	0.93	C9—H9	0.93
C4—C5	1.380 (2)	C7—C6	1.356 (3)
C4—C9	1.388 (2)	C6—H6	0.93
C4—C3	1.453 (2)	C15—C14	1.370 (3)
O1—C1	1.2255 (19)	C15—H15	0.93
C3—H3	0.93	C11—C12	1.378 (2)
C1—C10	1.490 (2)	C11—H11	0.93
F1—C7	1.3615 (19)	C13—C12	1.358 (3)
C10—C11	1.372 (2)	C13—C14	1.365 (3)
C10—C15	1.374 (2)	C13—H13	0.93
C8—C7	1.356 (3)	C12—H12	0.93
C8—C9	1.372 (2)	C14—H14	0.93
C8—H8	0.93

C3—C2—C1	122.11 (15)	C4—C9—H9	119.5
C3—C2—H2	118.9	C8—C7—C6	122.65 (17)
C1—C2—H2	118.9	C8—C7—F1	119.12 (19)
C5—C4—C9	117.80 (15)	C6—C7—F1	118.23 (18)
C5—C4—C3	119.76 (15)	C7—C6—C5	118.00 (17)
C9—C4—C3	122.44 (15)	C7—C6—H6	121
C2—C3—C4	128.77 (15)	C5—C6—H6	121
C2—C3—H3	115.6	C14—C15—C10	121.52 (18)
C4—C3—H3	115.6	C14—C15—H15	119.2
O1—C1—C2	120.43 (15)	C10—C15—H15	119.2
O1—C1—C10	119.37 (15)	C10—C11—C12	120.78 (17)
C2—C1—C10	120.20 (14)	C10—C11—H11	119.6
C11—C10—C15	117.77 (16)	C12—C11—H11	119.6
C11—C10—C1	123.94 (15)	C12—C13—C14	119.57 (18)
C15—C10—C1	118.29 (15)	C12—C13—H13	120.2
C7—C8—C9	118.99 (18)	C14—C13—H13	120.2
C7—C8—H8	120.5	C13—C12—C11	120.46 (18)
C9—C8—H8	120.5	C13—C12—H12	119.8
C4—C5—C6	121.60 (17)	C11—C12—H12	119.8
C4—C5—H5	119.2	C13—C14—C15	119.88 (19)
C6—C5—H5	119.2	C13—C14—H14	120.1
C8—C9—C4	120.94 (17)	C15—C14—H14	120.1
C8—C9—H9	119.5

C1—C2—C3—C4	−179.76 (16)	C9—C8—C7—C6	−0.8 (3)
C5—C4—C3—C2	173.35 (17)	C9—C8—C7—F1	−179.91 (16)
C9—C4—C3—C2	−6.9 (3)	C8—C7—C6—C5	1.4 (3)
C3—C2—C1—O1	−7.3 (3)	F1—C7—C6—C5	−179.52 (16)
C3—C2—C1—C10	172.77 (16)	C4—C5—C6—C7	−0.7 (3)
O1—C1—C10—C11	−171.95 (19)	C11—C10—C15—C14	0.5 (3)
C2—C1—C10—C11	8.0 (3)	C1—C10—C15—C14	−179.2 (2)
O1—C1—C10—C15	7.7 (3)	C15—C10—C11—C12	−0.8 (3)
C2—C1—C10—C15	−172.33 (18)	C1—C10—C11—C12	178.88 (17)
C9—C4—C5—C6	−0.6 (2)	C14—C13—C12—C11	0.8 (3)
C3—C4—C5—C6	179.19 (16)	C10—C11—C12—C13	0.1 (3)
C7—C8—C9—C4	−0.5 (3)	C12—C13—C14—C15	−1.1 (4)
C5—C4—C9—C8	1.2 (3)	C10—C15—C14—C13	0.4 (4)
C3—C4—C9—C8	−178.60 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1ⁱ	0.93	2.49	3.244 (2)	138
C13—H13···F1ⁱⁱ	0.93	2.68	3.465 (2)	142

Symmetry codes: (i) −x+1, −y, −z; (ii) x+1, −y+3/2, z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1ⁱ	0.93	2.49	3.244 (2)	138
C13—H13···F1ⁱⁱ	0.93	2.68	3.465 (2)	142

Symmetry codes: (i) −x+1, −y, −z; (ii) x+1, −y+3/2, z+1/2.

Acknowledgements

The authors wish to acknowledge CONACyT–Gobierno del Estado Tabasco and the Universidad Juárez Autónoma de Tabasco for financial support via projects TAB-2009-C18–122141 and UJAT-2011-C07–22, respectively.

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