Second monoclinic form of (E)-3-(4-fluoro-phen-yl)-1-phenyl-prop-2-en-1-one.

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-fluoro-phenyl group opposite to the benzoyl group. The torsion angle of between the planes of the 4-fluoro-phenyl and benzoyl groups is 10.53 (6)°. In the crystal, weak C-H⋯O and C-H⋯F inter-actions form a cross-linked packing motif, building sheets parallel to (-102).

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 = 226.24

Monoclinic,

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 ▶) 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[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.131

S = 1.01

2276 reflections

155 parameters

H-atom parameters constrained

Δρmax = 0.11 e Å−3

Δρmin = −0.11 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); 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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813028079/bh2484sup1.cif

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

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813028079/bh2484Isup3.cml

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

C15H11FO	F(000) = 472
Mr = 226.24	Dx = 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

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

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(Fo2) + (0.0624P)2 + 0.1205P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
2276 reflections	Δρmax = 0.11 e Å−3
155 parameters	Δρmin = −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

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) .