1-Ferrocenyl-3-(2-methyl­anilino)propan-1-one

Leka, Z.; Novaković, S.B.; Pejović, A.; Bogdanović, G.A.; Vukićević, R.D.

doi:10.1107/S1600536812028802

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 7| July 2012| Pages m995-m996

https://doi.org/10.1107/S1600536812028802

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1-Ferrocenyl-3-(2-methylanilino)propan-1-one

Zorica Leka,^a ^* Sladjana B. Novaković,^b Anka Pejović,^c Goran A. Bogdanović ^b and Rastko D. Vukićević ^c

^aFaculty of Metallurgy and Technology, University of Montenegro, Cetinjski put bb, 81000 Podgorica, Montenegro, ^b'Vinča' Institute of Nuclear Sciences, Laboratory of Theoretical Physics and Condensed Matter Physics, PO Box 522, University of Belgrade, 11001 Belgrade, Serbia, and ^cDepartment of Chemistry, Faculty of Science, University of Kragujevac, R. Domanovića 12, 34000 Kragujevac, Serbia
^*Correspondence e-mail: zorica@ac.me

(Received 20 June 2012; accepted 25 June 2012; online 30 June 2012)

In the ferrocene-containing Mannich base, [Fe(C₅H₅)(C₁₅H₁₆NO)], the dihedral angle between the mean planes of the benzene ring and the substituted cyclopentadienyl ring is 84.63 (7)°. The conformation of the title compound significantly differs from those found in corresponding m-tolylamino and p-tolylamino derivatives. In the crystal, C—H⋯O interactions connect the molecules into chains, which further interact by means of C—H⋯π interactions. It is noteworthy that the amino H atom is shielded and is not involved in hydrogen bonding.

Related literature

For the physico-chemical properties of ferrocene-based compounds see: Togni & Hayashi (1995 ). For related structures and details of the synthesis, see: Damljanović et al. (2011 ); Pejović et al. (2012 ); Stevanović et al. (2012 ); Leka et al. (2012a ,b ,c ).

Experimental

Crystal data

[Fe(C₅H₅)(C₁₅H₁₆NO)]
M_r = 347.23
Monoclinic, P 2₁ /c
a = 12.1343 (4) Å
b = 17.8010 (7) Å
c = 7.5464 (2) Å
β = 92.946 (3)°
V = 1627.89 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.93 mm⁻¹
T = 293 K
0.22 × 0.18 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ )' T_min = 0.923, T_max = 1.000
7605 measured reflections
3694 independent reflections
2843 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.097
S = 1.04
3694 reflections
213 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C14–C19 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12A⋯O1ⁱ	0.97	2.38	3.182 (3)	139
C19—H19⋯Cg1ⁱ	0.93	2.98	3.838 (3)	160
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ), PLATON (Spek, 2009 ) and PARST (Nardelli, 1995 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812028802/bt5950sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812028802/bt5950Isup2.hkl

checkCIF report

Comment top

The title compound 1-Ferrocenyl-3-(o-tolylamino)propan-1-one (I), Fig. 1, shows considerable conformational differences in comparison to the crystal structures of two closely related derivatives, 1-Ferrocenyl-4-(m-tolylamino)propan-1-one (Pejović et al., 2012) and 1-Ferrocenyl-3-(p-tolylamino)propan-1-one (Leka et al., 2012b). The torsion angles C1—C11—C12—C13, C11—C12—C13—N1 and C12—C13—N1—C4 within the aliphatic fragment have the values of -161.7 (2), 78.9 (3) and 168.9 (2)°. The latter torsion angle which defines the final orientation of the phenyl ring significantly differs from the values found in m-tolylamino [69.4 (4)°] and p-tolylamino [70.6 (3)°] derivatives. On the other hand, the conformation of the title compound is closer to the one found in those 3-(arylamino)-1-ferrocenylpropan-1-ones which comprise other ortho substituted arylamino fragments, such as previously reported 1-Ferrocenyl-3-(2-acetylphenylamino)propan-1-one (Stevanović et al., 2012) and 1-Ferrocenyl-3-(2-nitrophenylamino)propan-1-one (Damljanović et al., 2011), [the torsion angle C12—C13—N1—C4 in these compounds has the value -176.1 (6) and -175.7 (6)° respectively]. In the molecule of (I) the phenyl ring is nearly orthogonally positioned with regard to substituted Cp ring. The dihedral angle between the mean planes of the phenyl ring and the substituted Cp ring is 84.63 (7)°. The Cp rings within the Fc unit display nearly eclipsed conformation with C1—Cg1—Cg2—C6 angle of 9.93° (Cg is centroid of the corresponding Cp ring). The molecules of (I) connect via C12–H12a···O1 interaction into zigzag chain extended along c axis (Fig. 2). The chains are further related by means of extensive C—H···π interactions, C19—H19···Cg1ⁱ: H···Cg 2.98 Å, H-Perp 2.87 Å, X—H···Cg 160°, (i = x, -y + 1/2, z - 1/2); C8—H8···Cg1ⁱⁱ: H···Cg 3.02 Å, H-Perp 2.84 Å, X—H···Cg 140° (ii = -x + 1, -y, -z + 1); C13—H13b···Cg1ⁱ: H···Cg 3.35 Å, H-Perp 2.87 Å, X—H···Cg 127°; C16—H16···Cg2ⁱⁱⁱ: H···Cg 3.07 Å, H-Perp 2.97 Å, X—H···Cg 168 ° (iii = -x + 1, -y, -z + 1); C20—H20a···Cg2ⁱⁱⁱ: H···Cg 3.38 Å, H-Perp 2.95 Å, X—H···Cg 140° (Cg1 and Cg2 are centroids of phenyl and unsubstituted Cp ring respectively).

Related literature top

For the physico-chemical properties of ferrocene-based compounds see: Togni & Hayashi (1995). For related structures and details of the synthesis, see: Damljanović et al. (2011); Pejović et al. (2012); Stevanović et al. (2012); Leka et al. (2012a,b,c).

Experimental top

The compound was obtained by an aza-Michael addition of the coresponding arylamine to acryloylferrocene. The reaction was performed by microwave (MW) irradiation (500 W/5 min) of a mixture of reactants and montmorillonite K-10, without a solvent as described by Damljanović et al. (2011).

Structure description top

For the physico-chemical properties of ferrocene-based compounds see: Togni & Hayashi (1995). For related structures and details of the synthesis, see: Damljanović et al. (2011); Pejović et al. (2012); Stevanović et al. (2012); Leka et al. (2012a,b,c).

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: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999), PLATON (Spek, 2009) and PARST (Nardelli, 1995).

Figures top

	Fig. 1. The molecular structure of (I), with atom labels and 40% probability displacement ellipsoids for non-H atoms.
	Fig. 2. Segment of the crystal packing. The C12—H···O1 interactions connecting the molecules into chains are indicated by black dotted lines. C—H···π interactions are given in blue doted lines.

1-Ferrocenyl-3-(2-methylanilino)propan-1-one top

Crystal data top

[Fe(C₅H₅)(C₁₅H₁₆NO)]	F(000) = 728
M_r = 347.23	D_x = 1.417 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3389 reflections
a = 12.1343 (4) Å	θ = 3.3–28.9°
b = 17.8010 (7) Å	µ = 0.93 mm⁻¹
c = 7.5464 (2) Å	T = 293 K
β = 92.946 (3)°	Prismatic, orange
V = 1627.89 (9) Å³	0.22 × 0.18 × 0.12 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur Sapphire3 Gemini diffractometer	3694 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2843 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
Detector resolution: 16.3280 pixels mm^-1	θ_max = 29.0°, θ_min = 3.3°
ω scans	h = −15→16
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)'	k = −22→19
T_min = 0.923, T_max = 1.000	l = −10→9
7605 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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0396P)² + 0.2313P] where P = (F_o² + 2F_c²)/3
3694 reflections	(Δ/σ)_max < 0.001
213 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

[Fe(C₅H₅)(C₁₅H₁₆NO)]	V = 1627.89 (9) Å³
M_r = 347.23	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.1343 (4) Å	µ = 0.93 mm⁻¹
b = 17.8010 (7) Å	T = 293 K
c = 7.5464 (2) Å	0.22 × 0.18 × 0.12 mm
β = 92.946 (3)°

Data collection top

Oxford Diffraction Xcalibur Sapphire3 Gemini diffractometer	3694 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)'	2843 reflections with I > 2σ(I)
T_min = 0.923, T_max = 1.000	R_int = 0.029
7605 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.28 e Å⁻³
3694 reflections	Δρ_min = −0.28 e Å⁻³
213 parameters

Special details top

Experimental. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. 'CrysAlisPro, (Oxford Diffraction, 2009)'

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

	x	y	z	U_iso*/U_eq
Fe	0.80589 (2)	0.094395 (18)	0.51346 (4)	0.03546 (12)
O1	0.61741 (15)	0.26845 (11)	0.5452 (2)	0.0615 (5)
N1	0.41087 (17)	0.15206 (13)	0.4050 (2)	0.0427 (5)
C1	0.73752 (18)	0.17593 (14)	0.6608 (3)	0.0382 (5)
C2	0.76352 (19)	0.11125 (15)	0.7678 (3)	0.0445 (6)
H2	0.7136	0.0826	0.8284	0.053*
C3	0.8779 (2)	0.09863 (17)	0.7649 (3)	0.0541 (7)
H3	0.9167	0.0604	0.8244	0.065*
C4	0.9240 (2)	0.15390 (17)	0.6566 (3)	0.0538 (7)
H4	0.9980	0.1580	0.6319	0.065*
C5	0.83831 (19)	0.20199 (14)	0.5919 (3)	0.0452 (6)
H5	0.8461	0.2432	0.5179	0.054*
C6	0.7064 (2)	0.07479 (17)	0.2926 (3)	0.0570 (7)
H6	0.6430	0.1015	0.2583	0.068*
C7	0.7122 (2)	0.01088 (18)	0.4021 (3)	0.0616 (8)
H7	0.6528	−0.0122	0.4534	0.074*
C8	0.8221 (3)	−0.01211 (16)	0.4207 (3)	0.0595 (7)
H8	0.8489	−0.0531	0.4860	0.071*
C9	0.8845 (2)	0.03759 (17)	0.3236 (3)	0.0565 (7)
H9	0.9605	0.0354	0.3135	0.068*
C10	0.8143 (2)	0.09090 (16)	0.2445 (3)	0.0551 (7)
H10	0.8351	0.1303	0.1724	0.066*
C11	0.62784 (18)	0.20805 (14)	0.6183 (3)	0.0395 (5)
C12	0.52948 (18)	0.16387 (15)	0.6742 (3)	0.0451 (6)
H12A	0.5231	0.1704	0.8009	0.054*
H12B	0.5430	0.1110	0.6531	0.054*
C13	0.42057 (18)	0.18528 (15)	0.5804 (3)	0.0451 (6)
H13A	0.3602	0.1681	0.6495	0.054*
H13B	0.4157	0.2395	0.5705	0.054*
C14	0.31120 (17)	0.15273 (13)	0.3047 (3)	0.0366 (5)
C15	0.30246 (19)	0.11137 (14)	0.1457 (3)	0.0422 (6)
C16	0.2019 (2)	0.10971 (17)	0.0517 (3)	0.0562 (7)
H16	0.1951	0.0822	−0.0531	0.067*
C17	0.1113 (2)	0.14773 (18)	0.1089 (3)	0.0621 (8)
H17	0.0443	0.1455	0.0436	0.075*
C18	0.1206 (2)	0.18863 (17)	0.2619 (3)	0.0551 (7)
H18	0.0597	0.2144	0.3007	0.066*
C19	0.22021 (18)	0.19193 (15)	0.3598 (3)	0.0442 (6)
H19	0.2262	0.2206	0.4629	0.053*
C20	0.4006 (2)	0.06922 (17)	0.0836 (3)	0.0593 (7)
H20A	0.3801	0.0429	−0.0241	0.089*
H20B	0.4254	0.0339	0.1731	0.089*
H20C	0.4589	0.1040	0.0622	0.089*
H1N	0.463 (2)	0.1487 (15)	0.361 (3)	0.052 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe	0.04343 (19)	0.0331 (2)	0.02940 (16)	−0.00300 (14)	−0.00236 (12)	−0.00362 (14)
O1	0.0637 (11)	0.0499 (13)	0.0697 (12)	−0.0005 (9)	−0.0097 (9)	0.0184 (10)
N1	0.0387 (11)	0.0526 (14)	0.0366 (9)	0.0025 (10)	0.0018 (9)	−0.0108 (10)
C1	0.0475 (12)	0.0382 (14)	0.0286 (10)	−0.0034 (11)	−0.0008 (9)	−0.0081 (10)
C2	0.0543 (14)	0.0534 (17)	0.0253 (10)	0.0012 (12)	−0.0033 (9)	−0.0030 (10)
C3	0.0615 (15)	0.0616 (19)	0.0371 (12)	0.0104 (14)	−0.0174 (11)	−0.0100 (13)
C4	0.0417 (13)	0.066 (2)	0.0525 (14)	−0.0044 (13)	−0.0062 (11)	−0.0228 (14)
C5	0.0523 (13)	0.0360 (14)	0.0470 (12)	−0.0104 (11)	−0.0011 (11)	−0.0123 (11)
C6	0.0605 (16)	0.063 (2)	0.0455 (13)	0.0130 (14)	−0.0213 (12)	−0.0222 (14)
C7	0.0712 (18)	0.063 (2)	0.0509 (15)	−0.0302 (16)	0.0080 (13)	−0.0229 (15)
C8	0.092 (2)	0.0336 (15)	0.0512 (14)	0.0059 (15)	−0.0086 (14)	−0.0064 (12)
C9	0.0569 (15)	0.0592 (19)	0.0537 (14)	0.0019 (14)	0.0053 (12)	−0.0216 (14)
C10	0.0856 (19)	0.0499 (17)	0.0303 (11)	−0.0067 (15)	0.0063 (12)	−0.0028 (12)
C11	0.0498 (13)	0.0404 (14)	0.0276 (10)	−0.0020 (11)	−0.0043 (9)	−0.0072 (10)
C12	0.0511 (13)	0.0520 (16)	0.0317 (10)	−0.0039 (12)	−0.0020 (10)	−0.0023 (11)
C13	0.0446 (12)	0.0535 (16)	0.0372 (11)	0.0015 (12)	0.0017 (10)	−0.0112 (11)
C14	0.0387 (11)	0.0341 (13)	0.0369 (11)	−0.0062 (10)	0.0008 (9)	0.0024 (10)
C15	0.0497 (13)	0.0415 (15)	0.0354 (11)	−0.0109 (11)	0.0018 (10)	−0.0002 (10)
C16	0.0656 (17)	0.0599 (19)	0.0420 (12)	−0.0195 (14)	−0.0068 (12)	−0.0023 (13)
C17	0.0501 (15)	0.078 (2)	0.0561 (15)	−0.0146 (15)	−0.0152 (12)	0.0190 (15)
C18	0.0456 (14)	0.0583 (19)	0.0612 (15)	0.0025 (13)	0.0007 (12)	0.0160 (14)
C19	0.0446 (13)	0.0440 (15)	0.0437 (12)	0.0000 (11)	0.0008 (10)	0.0024 (11)
C20	0.0690 (17)	0.0640 (19)	0.0454 (13)	−0.0064 (15)	0.0067 (12)	−0.0200 (14)

Geometric parameters (Å, º) top

Fe—C7	2.028 (3)	C7—C8	1.395 (4)
Fe—C1	2.031 (2)	C7—H7	0.9300
Fe—C9	2.031 (2)	C8—C9	1.397 (4)
Fe—C8	2.034 (3)	C8—H8	0.9300
Fe—C2	2.034 (2)	C9—C10	1.389 (4)
Fe—C5	2.037 (2)	C9—H9	0.9300
Fe—C6	2.037 (2)	C10—H10	0.9300
Fe—C10	2.039 (2)	C11—C12	1.507 (3)
Fe—C4	2.045 (2)	C12—C13	1.515 (3)
Fe—C3	2.049 (2)	C12—H12A	0.9700
O1—C11	1.212 (3)	C12—H12B	0.9700
N1—C14	1.393 (3)	C13—H13A	0.9700
N1—C13	1.449 (3)	C13—H13B	0.9700
N1—H1N	0.74 (2)	C14—C19	1.388 (3)
C1—C5	1.431 (3)	C14—C15	1.407 (3)
C1—C2	1.432 (3)	C15—C16	1.380 (3)
C1—C11	1.469 (3)	C15—C20	1.503 (3)
C2—C3	1.408 (3)	C16—C17	1.379 (4)
C2—H2	0.9300	C16—H16	0.9300
C3—C4	1.413 (4)	C17—C18	1.365 (4)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.414 (3)	C18—C19	1.385 (3)
C4—H4	0.9300	C18—H18	0.9300
C5—H5	0.9300	C19—H19	0.9300
C6—C7	1.406 (4)	C20—H20A	0.9600
C6—C10	1.406 (4)	C20—H20B	0.9600
C6—H6	0.9300	C20—H20C	0.9600

C7—Fe—C1	120.96 (11)	C1—C5—Fe	69.19 (13)
C7—Fe—C9	67.46 (11)	C4—C5—H5	126.1
C1—Fe—C9	164.08 (11)	C1—C5—H5	126.1
C7—Fe—C8	40.19 (11)	Fe—C5—H5	126.2
C1—Fe—C8	154.66 (11)	C7—C6—C10	107.3 (2)
C9—Fe—C8	40.20 (11)	C7—C6—Fe	69.41 (14)
C7—Fe—C2	109.60 (10)	C10—C6—Fe	69.88 (14)
C1—Fe—C2	41.25 (9)	C7—C6—H6	126.3
C9—Fe—C2	152.81 (11)	C10—C6—H6	126.3
C8—Fe—C2	119.71 (11)	Fe—C6—H6	126.0
C7—Fe—C5	154.91 (12)	C8—C7—C6	108.3 (2)
C1—Fe—C5	41.17 (9)	C8—C7—Fe	70.14 (15)
C9—Fe—C5	125.61 (11)	C6—C7—Fe	70.12 (15)
C8—Fe—C5	162.90 (11)	C8—C7—H7	125.8
C2—Fe—C5	69.00 (10)	C6—C7—H7	125.8
C7—Fe—C6	40.47 (11)	Fe—C7—H7	125.5
C1—Fe—C6	109.19 (10)	C7—C8—C9	107.6 (3)
C9—Fe—C6	67.52 (11)	C7—C8—Fe	69.67 (16)
C8—Fe—C6	67.82 (11)	C9—C8—Fe	69.81 (15)
C2—Fe—C6	128.99 (10)	C7—C8—H8	126.2
C5—Fe—C6	119.76 (11)	C9—C8—H8	126.2
C7—Fe—C10	67.72 (11)	Fe—C8—H8	125.9
C1—Fe—C10	127.57 (10)	C10—C9—C8	108.7 (2)
C9—Fe—C10	39.91 (11)	C10—C9—Fe	70.32 (14)
C8—Fe—C10	67.56 (11)	C8—C9—Fe	69.99 (15)
C2—Fe—C10	166.37 (11)	C10—C9—H9	125.6
C5—Fe—C10	107.41 (11)	C8—C9—H9	125.6
C6—Fe—C10	40.37 (11)	Fe—C9—H9	125.6
C7—Fe—C4	164.04 (13)	C9—C10—C6	108.0 (2)
C1—Fe—C4	68.63 (9)	C9—C10—Fe	69.76 (14)
C9—Fe—C4	106.77 (10)	C6—C10—Fe	69.75 (13)
C8—Fe—C4	125.95 (12)	C9—C10—H10	126.0
C2—Fe—C4	68.27 (10)	C6—C10—H10	126.0
C5—Fe—C4	40.53 (10)	Fe—C10—H10	126.0
C6—Fe—C4	152.92 (12)	O1—C11—C1	121.1 (2)
C10—Fe—C4	118.16 (11)	O1—C11—C12	121.6 (2)
C7—Fe—C3	127.89 (12)	C1—C11—C12	117.2 (2)
C1—Fe—C3	68.51 (10)	C11—C12—C13	115.0 (2)
C9—Fe—C3	118.55 (11)	C11—C12—H12A	108.5
C8—Fe—C3	107.98 (11)	C13—C12—H12A	108.5
C2—Fe—C3	40.32 (9)	C11—C12—H12B	108.5
C5—Fe—C3	68.25 (11)	C13—C12—H12B	108.5
C6—Fe—C3	166.04 (12)	H12A—C12—H12B	107.5
C10—Fe—C3	151.91 (12)	N1—C13—C12	110.61 (18)
C4—Fe—C3	40.37 (11)	N1—C13—H13A	109.5
C14—N1—C13	121.34 (19)	C12—C13—H13A	109.5
C14—N1—H1N	120 (2)	N1—C13—H13B	109.5
C13—N1—H1N	115 (2)	C12—C13—H13B	109.5
C5—C1—C2	107.3 (2)	H13A—C13—H13B	108.1
C5—C1—C11	125.2 (2)	C19—C14—N1	121.6 (2)
C2—C1—C11	127.4 (2)	C19—C14—C15	119.5 (2)
C5—C1—Fe	69.63 (13)	N1—C14—C15	118.9 (2)
C2—C1—Fe	69.49 (13)	C16—C15—C14	118.4 (2)
C11—C1—Fe	123.35 (14)	C16—C15—C20	121.5 (2)
C3—C2—C1	108.0 (2)	C14—C15—C20	120.1 (2)
C3—C2—Fe	70.41 (13)	C17—C16—C15	121.8 (2)
C1—C2—Fe	69.26 (11)	C17—C16—H16	119.1
C3—C2—H2	126.0	C15—C16—H16	119.1
C1—C2—H2	126.0	C18—C17—C16	119.6 (2)
Fe—C2—H2	125.9	C18—C17—H17	120.2
C2—C3—C4	108.5 (2)	C16—C17—H17	120.2
C2—C3—Fe	69.26 (12)	C17—C18—C19	120.4 (3)
C4—C3—Fe	69.64 (13)	C17—C18—H18	119.8
C2—C3—H3	125.7	C19—C18—H18	119.8
C4—C3—H3	125.7	C18—C19—C14	120.3 (2)
Fe—C3—H3	126.9	C18—C19—H19	119.8
C3—C4—C5	108.4 (2)	C14—C19—H19	119.8
C3—C4—Fe	69.99 (14)	C15—C20—H20A	109.5
C5—C4—Fe	69.44 (13)	C15—C20—H20B	109.5
C3—C4—H4	125.8	H20A—C20—H20B	109.5
C5—C4—H4	125.8	C15—C20—H20C	109.5
Fe—C4—H4	126.4	H20A—C20—H20C	109.5
C4—C5—C1	107.8 (2)	H20B—C20—H20C	109.5
C4—C5—Fe	70.03 (14)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C14–C19 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···O1ⁱ	0.97	2.38	3.182 (3)	139
C19—H19···Cg1ⁱ	0.93	2.98	3.838 (3)	160

Symmetry code: (i) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	[Fe(C₅H₅)(C₁₅H₁₆NO)]
M_r	347.23
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	12.1343 (4), 17.8010 (7), 7.5464 (2)
β (°)	92.946 (3)
V (Å³)	1627.89 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.93
Crystal size (mm)	0.22 × 0.18 × 0.12

Data collection
Diffractometer	Oxford Diffraction Xcalibur Sapphire3 Gemini
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)'
T_min, T_max	0.923, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	7605, 3694, 2843
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.681

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.097, 1.04
No. of reflections	3694
No. of parameters	213
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.28

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006), WinGX (Farrugia, 1999), PLATON (Spek, 2009) and PARST (Nardelli, 1995).

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C14–C19 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···O1ⁱ	0.97	2.38	3.182 (3)	139
C19—H19···Cg1ⁱ	0.93	2.98	3.838 (3)	160

Symmetry code: (i) x, −y+1/2, z+1/2.

Acknowledgements

This work was supported by the Ministry of Education and Science of the Republic of Serbia (project Nos. 172014, 172035 and 172034).

References

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Volume 68| Part 7| July 2012| Pages m995-m996

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