1-Ferrocenyl-3-(2-methyl-anilino)propan-1-one.

In the ferrocene-containing Mannich base, [Fe(C(5)H(5))(C(15)H(16)NO)], the dihedral angle between the mean planes of the benzene ring and the substituted cyclo-penta-dienyl ring is 84.63 (7)°. The conformation of the title compound significantly differs from those found in corresponding m-tolyl-amino and p-tolyl-amino derivatives. In the crystal, C-H⋯O inter-actions connect the mol-ecules into chains, which further inter-act by means of C-H⋯π inter-actions. 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 = 347.23

Monoclinic,

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 ▶)’ 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[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.097

S = 1.04

3694 reflections

213 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.28 e Å−3

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

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812028802/bt5950sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812028802/bt5950Isup2.hkl

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

[Fe(C5H5)(C15H16NO)]	F(000) = 728
Mr = 347.23	Dx = 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

Oxford Diffraction Xcalibur Sapphire3 Gemini diffractometer	3694 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2843 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
Detector resolution: 16.3280 pixels mm-1	θmax = 29.0°, θmin = 3.3°
ω scans	h = −15→16
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)'	k = −22→19
Tmin = 0.923, Tmax = 1.000	l = −10→9
7605 measured reflections

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(Fo2) + (0.0396P)2 + 0.2313P] where P = (Fo2 + 2Fc2)/3
3694 reflections	(Δ/σ)max < 0.001
213 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

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

	x	y	z	Uiso*/Ueq
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)*

	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)

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)

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

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) .