(E)-1-Ferrocenyl-3-(2-meth-oxy-phen-yl)prop-2-en-1-one.

The structure of the title compound, [Fe(C5H5)(C15H13O2)], consists of a ferrocenyl moiety and a 2-meth-oxy-phenyl group linked through a prop-2-en-1-one spacer in an E conformation. In the ferrocene unit, the substituted cyclo-penta-dienyl (Cps) ring and the unsubstituted cyclo-penta-dienyl ring (Cp) are almost parallel to one another [dihedral angle = 1.78 (14)°], and the Cp and Cps rings are in a gauche conformation. The benzene ring is twisted by 10.02 (14) and 11.38 (11)° with respect to the Cp and Cps rings, respectively. In the crystal, mol-ecules are linked by weak C-H⋯O hydrogen bonds into supra-molecular chains running along the b-axis direction.

Related literature

For the synthesis, see: Attar et al. (2011 ▶); Kumar et al. (2012 ▶). For related syntheses and background, see: Liu et al. (2001 ▶); Wu et al. (2002 ▶); Ji et al. (2003 ▶); Maree et al. (2008 ▶); Jiao et al. (2009 ▶); Cardona et al. (2010 ▶). For the biological activity of calcones and chalcone derivatives, see: Wu et al. (2002 ▶); Arezki et al. (2009 ▶); Nabi & Liu (2011 ▶); Zhao & Liu (2012 ▶). For related structures, see: Lindeman et al. (1997 ▶); Wu et al. (2006 ▶); Liu et al. (2008 ▶).

Experimental

Crystal data

[Fe(C5H5)(C15H13O2)]

M = 346.19

Orthorhombic,

a = 8.8352 (1) Å

b = 11.4047 (1) Å

c = 16.1327 (2) Å

V = 1625.58 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.93 mm−1

T = 296 K

0.22 × 0.17 × 0.12 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.821, T max = 0.896

13238 measured reflections

3659 independent reflections

3242 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.065

S = 1.05

3658 reflections

209 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.13 e Å−3

Absolute structure: Flack (1983 ▶), 1523 Friedel pairs

Absolute structure parameter: 0.004 (14)

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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 datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814003912/xu5769sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814003912/xu5769Isup2.hkl

CCDC reference: 987910

Additional supporting information: crystallographic information; 3D view; checkCIF report

[Fe(C5H5)(C15H13O2)]	Dx = 1.415 Mg m−3
Mr = 346.19	Melting point: 417 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 6681 reflections
a = 8.8352 (1) Å	θ = 2.9–26.8°
b = 11.4047 (1) Å	µ = 0.93 mm−1
c = 16.1327 (2) Å	T = 296 K
V = 1625.58 (3) Å3	Prism, red
Z = 4	0.22 × 0.17 × 0.12 mm
F(000) = 720

Bruker APEXII CCD diffractometer	3659 independent reflections
Radiation source: fine-focus sealed tube	3242 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
φ and ω scans	θmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −10→11
Tmin = 0.821, Tmax = 0.896	k = −14→14
13238 measured reflections	l = −20→20

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)] = 0.026	H-atom parameters constrained
wR(F2) = 0.065	w = 1/[σ2(Fo2) + (0.0341P)2 + 0.0721P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.002
3658 reflections	Δρmax = 0.21 e Å−3
209 parameters	Δρmin = −0.13 e Å−3
0 restraints	Absolute structure: Flack (1983), 1523 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.004 (14)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
C1	0.4177 (3)	0.4890 (3)	0.63912 (15)	0.0776 (7)
H1	0.3408	0.4925	0.5999	0.093*
C2	0.4854 (3)	0.5845 (2)	0.6769 (2)	0.0889 (10)
H2	0.4622	0.6629	0.6673	0.107*
C3	0.5963 (3)	0.5420 (3)	0.7327 (2)	0.0943 (9)
H3	0.6584	0.5869	0.7668	0.113*
C4	0.5945 (3)	0.4190 (3)	0.72679 (18)	0.0851 (8)
H4	0.6566	0.3679	0.7561	0.102*
C5	0.4835 (3)	0.3867 (2)	0.66940 (16)	0.0754 (7)
H5	0.4582	0.3106	0.6542	0.091*
C6	0.2005 (2)	0.39864 (16)	0.80793 (12)	0.0476 (4)
H6	0.1503	0.3369	0.7822	0.057*
C7	0.3176 (2)	0.3888 (2)	0.86594 (13)	0.0581 (5)
H7	0.3582	0.3188	0.8854	0.070*
C8	0.3639 (2)	0.5015 (2)	0.88996 (12)	0.0623 (5)
H8	0.4399	0.5188	0.9279	0.075*
C9	0.2754 (2)	0.58371 (17)	0.84677 (12)	0.0496 (4)
H9	0.2831	0.6648	0.8510	0.060*
C10	0.17163 (19)	0.52116 (16)	0.79522 (10)	0.0414 (4)
C11	0.06791 (18)	0.57653 (15)	0.73633 (12)	0.0437 (4)
C12	−0.00329 (19)	0.50151 (17)	0.67329 (12)	0.0499 (4)
H12	0.0185	0.4217	0.6729	0.060*
C13	−0.0981 (2)	0.54437 (16)	0.61665 (11)	0.0456 (4)
H13	−0.1167	0.6246	0.6188	0.055*
C14	−0.17574 (19)	0.47877 (17)	0.55157 (10)	0.0442 (4)
C15	−0.1691 (3)	0.35727 (18)	0.54580 (13)	0.0583 (5)
H15	−0.1111	0.3156	0.5838	0.070*
C16	−0.2464 (3)	0.2974 (2)	0.48517 (15)	0.0749 (7)
H16	−0.2408	0.2160	0.4829	0.090*
C17	−0.3305 (3)	0.3563 (2)	0.42873 (15)	0.0774 (7)
H17	−0.3814	0.3152	0.3874	0.093*
C18	−0.3413 (3)	0.4771 (2)	0.43210 (14)	0.0698 (6)
H18	−0.3999	0.5173	0.3936	0.084*
C19	−0.2647 (2)	0.53742 (19)	0.49291 (12)	0.0556 (5)
C20	−0.3610 (4)	0.7215 (2)	0.44401 (18)	0.1102 (12)
H20A	−0.3270	0.7087	0.3882	0.165*
H20B	−0.3554	0.8036	0.4568	0.165*
H20C	−0.4638	0.6953	0.4493	0.165*
O1	0.04308 (17)	0.68202 (11)	0.74047 (9)	0.0631 (4)
O2	−0.2676 (2)	0.65768 (14)	0.49974 (10)	0.0782 (5)
Fe1	0.38821 (3)	0.48092 (2)	0.764458 (16)	0.04441 (8)

	U11	U22	U33	U12	U13	U23
C1	0.0711 (15)	0.106 (2)	0.0554 (13)	0.0059 (15)	0.0217 (11)	0.0055 (13)
C2	0.095 (2)	0.0698 (16)	0.102 (2)	−0.0105 (15)	0.055 (2)	0.0035 (15)
C3	0.0524 (14)	0.127 (3)	0.103 (2)	−0.0362 (15)	0.0215 (18)	−0.0322 (19)
C4	0.0488 (13)	0.115 (2)	0.0920 (19)	0.0237 (13)	0.0192 (17)	−0.0047 (16)
C5	0.0735 (17)	0.0777 (16)	0.0751 (17)	0.0027 (13)	0.0224 (15)	−0.0200 (13)
C6	0.0461 (11)	0.0452 (9)	0.0514 (11)	−0.0029 (8)	0.0027 (9)	0.0070 (8)
C7	0.0579 (12)	0.0656 (12)	0.0507 (12)	0.0123 (10)	−0.0015 (10)	0.0139 (10)
C8	0.0543 (12)	0.0874 (16)	0.0454 (10)	0.0093 (11)	−0.0110 (9)	−0.0073 (10)
C9	0.0504 (11)	0.0512 (10)	0.0473 (10)	0.0025 (9)	0.0012 (9)	−0.0115 (8)
C10	0.0353 (8)	0.0479 (9)	0.0409 (8)	−0.0001 (8)	0.0049 (7)	0.0008 (8)
C11	0.0371 (9)	0.0465 (9)	0.0474 (10)	0.0036 (6)	0.0046 (8)	0.0028 (8)
C12	0.0429 (10)	0.0527 (11)	0.0540 (10)	0.0055 (8)	−0.0043 (8)	0.0021 (8)
C13	0.0378 (9)	0.0516 (10)	0.0475 (10)	0.0007 (8)	0.0034 (8)	0.0074 (7)
C14	0.0371 (8)	0.0533 (9)	0.0423 (9)	−0.0015 (8)	0.0048 (7)	0.0031 (8)
C15	0.0647 (13)	0.0588 (12)	0.0514 (12)	−0.0030 (10)	0.0029 (10)	0.0065 (9)
C16	0.101 (2)	0.0594 (13)	0.0644 (15)	−0.0176 (12)	0.0059 (15)	−0.0008 (11)
C17	0.0956 (19)	0.0832 (17)	0.0535 (13)	−0.0280 (14)	−0.0101 (14)	−0.0068 (12)
C18	0.0681 (13)	0.0886 (16)	0.0525 (12)	−0.0038 (13)	−0.0143 (10)	0.0043 (12)
C19	0.0510 (11)	0.0675 (13)	0.0484 (11)	0.0012 (10)	−0.0038 (9)	0.0011 (9)
C20	0.152 (3)	0.0934 (19)	0.0852 (19)	0.040 (2)	−0.044 (2)	0.0080 (15)
O1	0.0719 (9)	0.0497 (7)	0.0677 (9)	0.0134 (6)	−0.0116 (8)	0.0000 (7)
O2	0.1015 (14)	0.0633 (9)	0.0698 (10)	0.0214 (9)	−0.0350 (10)	−0.0010 (7)
Fe1	0.03514 (12)	0.04845 (13)	0.04965 (14)	−0.00074 (10)	0.00249 (11)	−0.00507 (10)

C1—C2	1.385 (4)	C9—Fe1	2.0326 (18)
C1—C5	1.391 (3)	C9—H9	0.9300
C1—Fe1	2.041 (2)	C10—C11	1.463 (3)
C1—H1	0.9300	C10—Fe1	2.0294 (17)
C2—C3	1.416 (4)	C11—O1	1.225 (2)
C2—Fe1	2.032 (3)	C11—C12	1.470 (3)
C2—H2	0.9300	C12—C13	1.332 (2)
C3—C4	1.406 (4)	C12—H12	0.9300
C3—Fe1	2.032 (2)	C13—C14	1.460 (3)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.398 (3)	C14—C15	1.390 (3)
C4—Fe1	2.047 (2)	C14—C19	1.400 (3)
C4—H4	0.9300	C15—C16	1.374 (3)
C5—Fe1	2.053 (2)	C15—H15	0.9300
C5—H5	0.9300	C16—C17	1.354 (3)
C6—C7	1.399 (3)	C16—H16	0.9300
C6—C10	1.435 (3)	C17—C18	1.382 (3)
C6—Fe1	2.0306 (18)	C17—H17	0.9300
C6—H6	0.9300	C18—C19	1.376 (3)
C7—C8	1.404 (3)	C18—H18	0.9300
C7—Fe1	2.043 (2)	C19—O2	1.376 (3)
C7—H7	0.9300	C20—O2	1.421 (3)
C8—C9	1.406 (3)	C20—H20A	0.9600
C8—Fe1	2.0496 (19)	C20—H20B	0.9600
C8—H8	0.9300	C20—H20C	0.9600
C9—C10	1.429 (3)
C2—C1—C5	109.0 (2)	C15—C14—C13	122.62 (17)
C2—C1—Fe1	69.79 (15)	C19—C14—C13	120.33 (17)
C5—C1—Fe1	70.60 (14)	C16—C15—C14	121.5 (2)
C2—C1—H1	125.5	C16—C15—H15	119.3
C5—C1—H1	125.5	C14—C15—H15	119.3
Fe1—C1—H1	125.7	C17—C16—C15	120.3 (2)
C1—C2—C3	108.0 (2)	C17—C16—H16	119.8
C1—C2—Fe1	70.46 (14)	C15—C16—H16	119.8
C3—C2—Fe1	69.58 (15)	C16—C17—C18	120.4 (2)
C1—C2—H2	126.0	C16—C17—H17	119.8
C3—C2—H2	126.0	C18—C17—H17	119.8
Fe1—C2—H2	125.5	C19—C18—C17	119.5 (2)
C4—C3—C2	106.9 (2)	C19—C18—H18	120.3
C4—C3—Fe1	70.41 (14)	C17—C18—H18	120.3
C2—C3—Fe1	69.63 (13)	O2—C19—C18	123.08 (19)
C4—C3—H3	126.6	O2—C19—C14	115.64 (17)
C2—C3—H3	126.6	C18—C19—C14	121.3 (2)
Fe1—C3—H3	125.0	O2—C20—H20A	109.5
C5—C4—C3	108.4 (3)	O2—C20—H20B	109.5
C5—C4—Fe1	70.30 (13)	H20A—C20—H20B	109.5
C3—C4—Fe1	69.26 (14)	O2—C20—H20C	109.5
C5—C4—H4	125.8	H20A—C20—H20C	109.5
C3—C4—H4	125.8	H20B—C20—H20C	109.5
Fe1—C4—H4	126.2	C19—O2—C20	118.09 (19)
C1—C5—C4	107.7 (3)	C10—Fe1—C6	41.40 (7)
C1—C5—Fe1	69.67 (13)	C10—Fe1—C3	146.85 (11)
C4—C5—Fe1	69.82 (13)	C6—Fe1—C3	169.96 (12)
C1—C5—H5	126.1	C10—Fe1—C2	115.91 (10)
C4—C5—H5	126.1	C6—Fe1—C2	148.66 (12)
Fe1—C5—H5	126.0	C3—Fe1—C2	40.79 (11)
C7—C6—C10	107.77 (18)	C10—Fe1—C9	41.18 (7)
C7—C6—Fe1	70.39 (12)	C6—Fe1—C9	68.92 (8)
C10—C6—Fe1	69.26 (10)	C3—Fe1—C9	114.23 (10)
C7—C6—H6	126.1	C2—Fe1—C9	109.02 (10)
C10—C6—H6	126.1	C10—Fe1—C1	110.65 (9)
Fe1—C6—H6	125.8	C6—Fe1—C1	117.87 (10)
C6—C7—C8	109.06 (18)	C3—Fe1—C1	67.62 (11)
C6—C7—Fe1	69.43 (11)	C2—Fe1—C1	39.76 (11)
C8—C7—Fe1	70.19 (12)	C9—Fe1—C1	133.16 (10)
C6—C7—H7	125.5	C10—Fe1—C7	68.43 (8)
C8—C7—H7	125.5	C6—Fe1—C7	40.18 (8)
Fe1—C7—H7	126.5	C3—Fe1—C7	130.91 (13)
C7—C8—C9	108.18 (17)	C2—Fe1—C7	170.14 (12)
C7—C8—Fe1	69.69 (12)	C9—Fe1—C7	67.87 (8)
C9—C8—Fe1	69.21 (11)	C1—Fe1—C7	148.88 (10)
C7—C8—H8	125.9	C10—Fe1—C4	171.98 (10)
C9—C8—H8	125.9	C6—Fe1—C4	132.11 (11)
Fe1—C8—H8	126.8	C3—Fe1—C4	40.33 (12)
C8—C9—C10	108.20 (17)	C2—Fe1—C4	67.53 (12)
C8—C9—Fe1	70.51 (11)	C9—Fe1—C4	146.05 (11)
C10—C9—Fe1	69.29 (10)	C1—Fe1—C4	66.89 (11)
C8—C9—H9	125.9	C7—Fe1—C4	109.43 (10)
C10—C9—H9	125.9	C10—Fe1—C8	68.51 (7)
Fe1—C9—H9	125.9	C6—Fe1—C8	68.04 (8)
C9—C10—C6	106.80 (16)	C3—Fe1—C8	107.73 (11)
C9—C10—C11	124.36 (17)	C2—Fe1—C8	131.63 (11)
C6—C10—C11	128.62 (17)	C9—Fe1—C8	40.28 (8)
C9—C10—Fe1	69.53 (10)	C1—Fe1—C8	170.76 (11)
C6—C10—Fe1	69.35 (11)	C7—Fe1—C8	40.11 (9)
C11—C10—Fe1	121.96 (12)	C4—Fe1—C8	115.22 (10)
O1—C11—C10	120.04 (18)	C10—Fe1—C5	133.45 (9)
O1—C11—C12	122.19 (17)	C6—Fe1—C5	110.56 (10)
C10—C11—C12	117.77 (15)	C3—Fe1—C5	67.68 (11)
C13—C12—C11	121.99 (18)	C2—Fe1—C5	67.16 (10)
C13—C12—H12	119.0	C9—Fe1—C5	172.29 (10)
C11—C12—H12	119.0	C1—Fe1—C5	39.73 (10)
C12—C13—C14	126.90 (18)	C7—Fe1—C5	117.05 (11)
C12—C13—H13	116.6	C4—Fe1—C5	39.88 (10)
C14—C13—H13	116.6	C8—Fe1—C5	147.23 (10)
C15—C14—C19	117.04 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1i	0.93	2.48	3.368 (2)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1i	0.93	2.48	3.368 (2)	159

Symmetry code: (i) .