(E)-1-Ferrocenyl-3-(2-meth­oxy­phen­yl)prop-2-en-1-one

Otaño Vega, M.R.; Rivero, K.I.; Montes González, I.

doi:10.1107/S1600536814003912

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 3| March 2014| Pages m108-m109

doi:10.1107/S1600536814003912

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(E)-1-Ferrocenyl-3-(2-methoxyphenyl)prop-2-en-1-one

Myrna R. Otaño Vega,^a Kennett I. Rivero ^a ^* and Ingrid Montes González ^a

^aDepartment of Chemistry, University of Puerto Rico, Río Piedras Campus, San Juan, Puerto Rico
^*Correspondence e-mail: rivero.ken@gmail.com

(Received 29 January 2014; accepted 19 February 2014; online 26 February 2014)

The structure of the title compound, [Fe(C₅H₅)(C₁₅H₁₃O₂)], consists of a ferrocenyl moiety and a 2-methoxyphenyl group linked through a prop-2-en-1-one spacer in an E conformation. In the ferrocene unit, the substituted cyclopentadienyl (Cps) ring and the unsubstituted cyclopentadienyl 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, molecules are linked by weak C—H⋯O hydrogen bonds into supramolecular chains running along the b-axis direction.

CCDC reference: 987910

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_r = 346.19
Orthorhombic, P 2₁ 2₁ 2₁
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[F² > 2σ(F²)] = 0.026
wR(F²) = 0.065
S = 1.05
3658 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.13 e Å⁻³
Absolute structure: Flack (1983 ), 1523 Friedel pairs
Absolute structure parameter: 0.004 (14)

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) $[-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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.

Supporting information

CCDC reference: 987910

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536814003912/xu5769sup1.cif

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

checkCIF report

Comment top

Chalcones occur in nature as precursors of flavonoids and exhibit various biological activities such as anti-cancer, anti-inflammatory, nitric oxide regulation and anti-hyperglycemic agents (Liu et al., 2001). They are traditionally synthesized in the laboratory, via the Claisen–Schmidt condensation carried out in basic or acidic media under homogeneous conditions (Attar et al., 2011). Structural modifications of the chalcone template are readily achieved. Biological activities of chalcones are equally wide ranging, such as: anti-bacterial and anti-hyperglycemic, anti-malarial, anti-HIV, anti-oxidant, and anti-tumor (Wu et al., 2002).

The crystal structure of the title compound reveals that the configuration about the C12═C13 bond corresponds to the (E)-isomer. The majority of the C and O atoms of the substituted cyclopentadienyl ring (Cps) are sp²-hybridized and the conjugation is lost at the methoxy substituent of C19. In the ferrocenyl moiety, the planes formed by the Cp (unsubstituted cyclopentadienyl ring) and Cps are almost parallel. The C atoms in these two rings have adopted a gauche conformation, and the Fe metal center lies closer to the Cps ring. The Fe—Cg and Fe—Cgs distances are 1.658 (2) and 1.644 (2) Å, respectively, where Cg and Cgs are the centroids of Cp and Cps, respectively. The Cg—Fe—Cgs angle is 178.4 (2)°.

Related literature top

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 top

The title compound was synthesized according to the literature procedure (Cardona et al., 2010). An aqueous solution of sodium hydroxide (5%, 2 ml) was added slowly with stirring to acetylferrocene (0.456 g, 0.002 mol). Then, 2-methoxybenzaldehyde (0.272 g, 0.002 mol) in ethanol (2 ml). The resulting mixture was stirred at room temperature for 2 h. The dark-orange-red precipitated solid was filtered off, washed with cold water and ethanol, dried and recrystallized from a mixture of acetone:water (yield, 84%; M·P. 144–145 °C). Dark violet crystals, suitable for X-ray diffraction, were obtained by the slow evaporation of a 1:1 (v/v) acetone:water solution of the title compound at room temperature over a period of 1 day. NMR analyses were performed on a Bruker AV-500 spectrometer by using CDCl₃ 99.9% pure as a solvent and Me₄Si as external standard.¹H-NMR (δ in p.p.m., CDCl₃): 3.90 (3H, s), 4.20 (5H, s), 4.60 (2H, s), 4.90 (2H, s), 7.05 (1H, d), 6.95, 7.25, 7.35, 8.10 (4H, dd, d,d, dd), 7.65 (1H, d). ¹³C-NMR (δ in p.p.m., CDCl₃): 55.5, 69.7, 70.1, 72.5, 80.9, 111.2, 123.9, 120.7, 124.7, 128.9, 131.2, 136.3, 158.7, 193.5.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound.

(E)-1-Ferrocenyl-3-(2-methoxyphenyl)prop-2-en-1-one top

Crystal data top

[Fe(C₅H₅)(C₁₅H₁₃O₂)]	D_x = 1.415 Mg m⁻³
M_r = 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

Data collection top

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

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)] = 0.026	H-atom parameters constrained
wR(F²) = 0.065	w = 1/[σ²(F_o²) + (0.0341P)² + 0.0721P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.002
3658 reflections	Δρ_max = 0.21 e Å⁻³
209 parameters	Δρ_min = −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)

Crystal data top

[Fe(C₅H₅)(C₁₅H₁₃O₂)]	V = 1625.58 (3) Å³
M_r = 346.19	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 8.8352 (1) Å	µ = 0.93 mm⁻¹
b = 11.4047 (1) Å	T = 296 K
c = 16.1327 (2) Å	0.22 × 0.17 × 0.12 mm

Data collection top

Bruker APEXII CCD diffractometer	3659 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	3242 reflections with I > 2σ(I)
T_min = 0.821, T_max = 0.896	R_int = 0.022
13238 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	H-atom parameters constrained
wR(F²) = 0.065	Δρ_max = 0.21 e Å⁻³
S = 1.05	Δρ_min = −0.13 e Å⁻³
3658 reflections	Absolute structure: Flack (1983), 1523 Friedel pairs
209 parameters	Absolute structure parameter: 0.004 (14)
0 restraints

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x, y−1/2, −z+3/2.

Hydrogen-bond geometry (Å, º) top

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) −x, y−1/2, −z+3/2.

Acknowledgements

The authors thank the Pfizer Pharmaceuticals Fellowship Program, the UPR–RP RISE Program (No. 2R25GM61151), and the Materials Characterization Center (MCC)-UPR Río Piedras.

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