(R)-N-(Ferrocenylmeth­yl)-1-hy­droxy-3-phenyl­propan-2-aminium (E)-but-2-enoate

Štěpnička, P.; Císařová, I.

doi:10.1107/S1600536811044096

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Pages m1619-m1620

doi:10.1107/S1600536811044096

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(R)-N-(Ferrocenylmethyl)-1-hydroxy-3-phenylpropan-2-aminium (E)-but-2-enoate

Petr Štěpnička ^a ^* and Ivana Císařová ^a

^aDepartment of Inorganic Chemistry, Faculty of Science, Charles University in Prague, Hlavova 2030, 12840 Prague 2, Czech Republic
^*Correspondence e-mail: stepnic@natur.cuni.cz

(Received 7 October 2011; accepted 24 October 2011; online 29 October 2011)

The crystal structure of the title salt, [Fe(C₅H₅)(C₁₅H₁₉NO)](C₄H₅O₂), consists of discrete ammonium and carboxylate ions, which associate into infinite chains parallel to [100] by means of N—H⋯O and O—H⋯O interactions. These chains are further cross-linked into a three-dimensional network by additional C—H⋯O contacts and by offset π–π stacking interactions of inversion-related aromatic rings [centroid–centroid distance = 3.7040 (14) Å]. The molecular parameters of the ionic components are in no way unexpected, the geometry of the ammonium cation being similar to that found in other structurally characterized salts obtained from N-ferrocenylmethyl β-aminoalcohols. The (E)-but-2-enoate anion consists of two approximately planar subunits, viz the delocalized carboxylate unit and the butenyl group (the latter being planar within ca. 0.002 Å), which are mutually rotated by 30.3 (4)°.

Related literature

For crystal structures of N-ferrocenylmethyl β-aminoalcohols and their salts, see: Štěpnička et al. (2004 , 2008a ,b ). For the preparation of a simple N-ferrocenylmethyl β-aminoalcohol, FcCH₂NHCH₂CH₂OH (Fc = ferrocenyl), see: Hess et al. (1999 ). For an overview of organometallic crystal engineering, see: Braga et al. (2008 ) and references cited therein.

Experimental

Crystal data

[Fe(C₅H₅)(C₁₅H₁₉NO)](C₄H₅O₂)
M_r = 435.33
Monoclinic, P 2₁
a = 5.9730 (2) Å
b = 15.3905 (3) Å
c = 11.7713 (4) Å
β = 100.4986 (13)°
V = 1063.99 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.73 mm⁻¹
T = 150 K
0.33 × 0.12 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer
15916 measured reflections
4864 independent reflections
4511 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.067
S = 1.05
4864 reflections
265 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.27 e Å⁻³
Absolute structure: Flack (1983 ), 2329 Friedel pairs
Flack parameter: −0.016 (12)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H91⋯O2ⁱ	0.95	1.74	2.685 (2)	173
N1—H92⋯O3	0.82	1.94	2.747 (2)	170
O1—H93⋯O3ⁱ	0.87	1.85	2.712 (2)	172
C16—H16⋯O1ⁱⁱ	0.93	2.56	3.447 (3)	159
C18—H18⋯O2ⁱⁱⁱ	0.93	2.58	3.435 (3)	154
Symmetry codes: (i) x-1, y, z; (ii) x+1, y, z; (iii) $[-x+1, y-{\script{1\over 2}}, -z+1]$ .

Data collection: COLLECT (Nonius, 2000 ); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97 and PLATON.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811044096/bh2388sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811044096/bh2388Isup2.hkl

checkCIF report

Comment top

With our recent work (Štěpnička et al., 2004 and 2008a,b), we demonstrated that N-ferrocenylmethyl β-aminoalcohols with general formula FcCH₂NHCR¹R²CR³R⁴OH (Fc = ferrocenyl) are potentially useful building blocks for organometallic crystal engineering (Braga et al., 2008 and references therein). These compounds possess a balanced number of conventional H-bond donors and acceptors (OH and NH) in their native form. When reacted with protonic acids, they are readily converted to the corresponding ammonium salts, the crystal assembly of which receives additional support from charge interactions. This contribution reports the crystal structure of a salt obtained from a chiral aminoalcohol, namely (R)-2-[(ferrocenylmethyl)azonia]-3-phenylpropan-1-ol (E)-but-2-enoate.

Several crystals of the title compound were isolated unexpectedly during attempted crystallization of (R)-2-[(ferrocenylmethyl)amino]-3-phenylpropan-1-ol from ethyl acetate/hexane, apparently resulting from the reaction of the free amine with (E)-but-2-enoic acid present as a trace impurity in reagent grade ethyl acetate. A view of the molecular structure is presented in Fig. 1.

The geometry of the cation is rather unexceptional, and compares well with those reported earlier for salts obtained from FcCH₂CMe₂CH₂OH and similar N-ferrocenylmethyl β-aminoalcohols (Štěpnička et al., 2004 and 2008a,b). The ferrocenylmethyl and benzyl group attached to the 'central' N1—C12 bond assume an anticlinal eclipsed conformation (cf. torsion angle C11—N1—C12—C14) while their aromatic rings, C(1–5) and C(15–20), are nearly parallel [dihedral angle 7.75 (12)°] but mutually offset. The CH₂OH pendant group is appended in a gauche position (cf. torsion angle C11—N1—C12—C13). Atom C13 is directed towards the ferrocenyl group and the C13—O1 bond extends away from the N1—C12 bond (cf. torsion angle N1—C12—C13—O1).

The ferrocenyl group shows negligible tilting [dihedral angle of the least-squares cyclopentadienyl planes is 1.63 (13)°] and similar Fe1—ring centroid distances [1.6461 (10) Å and 1.6565 (10) Å for the rings C(1–5) and C(6–10), respectively]. Although the Fe—C distances between Fe1 and individual carbon atoms in the substituted cyclopentadienyl ring C(1–5) differ by less than 0.03 Å [2.0271 (16)–2.054 (2) Å], there is a clear trend with the Fe—C distance gradually increasing from the C_ipso to the opposite edge of the five-membered ring (ipso < α < β). The Fe—C distances observed for the unsubstituted cyclopentadienyl ring vary significantly less [2.040 (2)–2.058 (2) Å].

The C═C double bond within the (E)-but-2-enoate anion has an almost ideal trans configuration with the torsion angle C21—C22—C23—C24 of -179.6 (3)°, which renders the whole CH₃—CH═CH—C group nearly perfectly planar (within ca. 0.002 Å). The terminal carboxyl group (C21, O2, O3) is symmetrically rotated from the plane of the CH₃—CH═ CH—C moiety by as much as 30.3 (4)° and shows a delocalized character. The individual C—O distances differ by only ca. 0.02 Å and even this relatively small difference may come mainly from crystal packing effects as the longer C—O distance is associated with O3 acting as a double H-bond acceptor, while the shorter one involves O2 atom for which only one strong H-bond was detected.

The ions constituting the crystal of the title compound assemble by means of H-bonds between OH and NH groups and carboxylate oxygen atoms to form infinite chains in the [1 0 0] direction (Fig. 2). Distances between the H-bond donors and acceptors are close to 2.7 Å while the H-bond angles fall into the range 170–173° (Table 2). In addition, these conventional H-bonds are supported by the softer C—H···O interactions formed by CH groups at the terminal phenyl ring and proximal oxygen atoms O1 and O2 and further by π···π stacking interactions between the unsubstituted cyclopentadienyl ring C(6–10) and phenyl ring in a molecule related by unit-cell translation along the c-axis (Fig. 3). Least-squares planes of the interacting aromatic rings make a dihedral angle of 6.22 (12)°, and the distance of their respective centroids is 3.7040 (14) Å.

Related literature top

For crystal structures of N-ferrocenylmethyl β-aminoalcohols and their salts, see: Štěpnička et al. (2004, 2008a,b). For the preparation of a simple N-ferrocenylmethyl β-aminoalcohol, FcCH₂NHCH₂CH₂OH (Fc = ferrocenyl), see: Hess et al. (1999). For an overview of organometallic crystal engineering, see: Braga et al. (2008) and references cited therein.

Experimental top

(R)-2-[(Ferrocenylmethyl)amino]-3-phenylpropan-1-ol was prepared by an established two-step procedure (Hess et al., 1999; Štěpnička et al. 2004 and 2008b) consisting of condensation of ferrocene carboxaldehyde with (R)-phenylalaninol and subsequent reduction of the intermediate Schiff base as follows.

Ferrocene carboxaldehyde (428 mg, 2.00 mmol) and (R)-2-amino-3-phenylpropan-1-ol (318 mg, 2.1 mmol) were dissolved in dry chloroform (20 ml). The resulting solution was refluxed under argon for 90 min and then evaporated under vacuum. The residue was immediately re-dissolved in dry methanol (20 ml) and the solution was cooled in ice. An amount of NaBH₄ (380 mg, 10 mmol) was added over 30 min causing the colour of the reaction mixture to change from initial orange red to orange yellow. After the addition, the reaction mixture was stirred at 0 °C for 1 h and at room temperature for 90 min before being quenched by addition of 10% aqueous NaOH and extracted with dichloromethane (2×20 ml). The combined organic extracts were washed with brine (2×20 ml) and dried over MgSO₄ overnight.

The drying agent was filtered off and the filtrate was evaporated under vacuum leaving a residue which was purified by column chromatography over silica gel. Elution with dichloromethane–methanol (10:1 v/v) led to the development of two yellow bands. The first one containing ferrocenylmethanol was discarded. The second one was collected and evaporated under vacuum to afford (R)-2-[(ferrocenylmethyl)amino]-3-phenylpropan-1-ol (371 mg, 53%) as an orange amorphous solid.

Characterization. ¹H NMR (CDCl₃): δ 2.31 (br s, 2 H, NH and OH), 2.78 (dd, ²J_HH = 13.7, ³J_HH = 6.7 Hz, 1 H, CH₂Ph), 2.83 (dd, ²J_HH = 13.7, ³J_HH = 7.6 Hz, 1 H, CH₂Ph), 3.01 (m, 1 H, CHN), 3.38 (dd, ²J_HH = 10.8, ³J_HH = 4.7 Hz, 1 H, CH₂O), 3.42 and 3.53 (2×d, ²J_HH = 12.9 Hz, 1 H, AB spin system of FcCH₂), 3.67 (dd, ²J_HH = 10.8, ³J_HH = 3.8 Hz, 1 H, CH₂O), 3.99 (s, 5 H, C₅H₅), 4.06 (m, 1 H, C₅H₄), 4.08 (virtual t, 2 H, C₅H₄), 4.14 (m, 1 H, C₅H₄), 7.18–7.34 (m, 5 H, Ph).

¹³C{¹H} NMR (CDCl₃): δ 38.15 (CH₂Ph), 46.01 (FcCH₂), 59.65 (CHN), 62.29 (CH₂O), 67.66 (2 C), 67.77 and 67.89 (CH of C₅H₄); 68.34 (C₅H₅), 86.61 (C_ipso of C₅H₄), 126.61 (1 C), 128.70 (2 C) and 129.18 (2 C) (3×CH of Ph); 138.44 (C_ipso of Ph).

IR (neat): ν/cm^-1 3296 br s, 3086 s, 3026 m, 2924 s, 2856 m, 1653 br m, 1603 w, 1495 s, 1454 very strong, 1412 m, 1352 m, 1329 m, 1232 m, 1105 very strong, 1041 very strong br, 1001 s, 818 br very strong, 746 very strong, 700 very strong, 484 very strong.

MS: m/z (relative abundance) 350 (9), 349 (38, M^+.), 347 (3), 331 (3, [M – H₂O]^+.), 266 (2), 200 (16), 199 (100, [FcCH₂]⁺), 197 (6), 186 (2, FcH^+.), 148 (3), 147 (3), 138 (2), 121 (28, [C₅H₅Fe]⁺), 91 (11), 78 (4), 77 (3), 65 (4), 56 (11, Fe⁺).

Few crystals of the title compound have been obtained upon attempted recrystallization of (R)-2-[(ferrocenylmethyl)amino]-3-phenylpropan-1-ol from ethyl acetate/hexane, resulting by a reaction of this compound with tiny amounts of (E)-but-2-enoic acid present in the commercial solvent (Lach-Ner).

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. View of the structure of the title compound showing displacement ellipsoids for non-H atoms at the 30% probability level.
	Fig. 2. Section of the infinite H-bonded chains in the crystal structure of the title compound. The bulky ferrocenyl moieties were replaced with filled squares for clarity.
	Fig. 3. π···π Stacking interactions of the aromatic rings in the structure of the title compound (indicated by a dotted line). The molecules depicted relate by unit-cell translation in the direction of the c-axis.

(R)-N-(Ferrocenylmethyl)-1-hydroxy-3-phenylpropan-2-aminium (E)-but-2-enoate top

Crystal data top

[Fe(C₅H₅)(C₁₅H₁₉NO)](C₄H₅O₂)	F(000) = 460
M_r = 435.33	D_x = 1.359 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 5.9730 (2) Å	Cell parameters from 2535 reflections
b = 15.3905 (3) Å	θ = 1.0–27.5°
c = 11.7713 (4) Å	µ = 0.73 mm⁻¹
β = 100.4986 (13)°	T = 150 K
V = 1063.99 (6) Å³	Block, yellow
Z = 2	0.33 × 0.12 × 0.10 mm

Data collection top

Nonius KappaCCD diffractometer	4511 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.043
Horizontally mounted graphite crystal monochromator	θ_max = 27.5°, θ_min = 3.2°
Detector resolution: 9.091 pixels mm^-1	h = −7→7
ω and ϕ scans to fill the Ewald sphere	k = −19→20
15916 measured reflections	l = −15→15
4864 independent reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.030	H-atom parameters constrained
wR(F²) = 0.067	w = 1/[σ²(F_o²) + (0.023P)² + 0.4582P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
4864 reflections	Δρ_max = 0.36 e Å⁻³
265 parameters	Δρ_min = −0.27 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 2329 Friedel pairs
0 constraints	Absolute structure parameter: −0.016 (12)
Primary atom site location: structure-invariant direct methods

Crystal data top

[Fe(C₅H₅)(C₁₅H₁₉NO)](C₄H₅O₂)	V = 1063.99 (6) Å³
M_r = 435.33	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 5.9730 (2) Å	µ = 0.73 mm⁻¹
b = 15.3905 (3) Å	T = 150 K
c = 11.7713 (4) Å	0.33 × 0.12 × 0.10 mm
β = 100.4986 (13)°

Data collection top

Nonius KappaCCD diffractometer	4511 reflections with I > 2σ(I)
15916 measured reflections	R_int = 0.043
4864 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	H-atom parameters constrained
wR(F²) = 0.067	Δρ_max = 0.36 e Å⁻³
S = 1.05	Δρ_min = −0.27 e Å⁻³
4864 reflections	Absolute structure: Flack (1983), 2329 Friedel pairs
265 parameters	Absolute structure parameter: −0.016 (12)
1 restraint

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

	x	y	z	U_iso*/U_eq
Fe1	0.34726 (4)	0.852498 (19)	1.26047 (2)	0.01975 (7)
N1	0.2364 (3)	0.79109 (11)	0.88685 (13)	0.0188 (3)
H91	0.1215	0.8326	0.8611	0.025 (6)*
H92	0.3616	0.8129	0.8869	0.045 (8)*
O1	−0.2057 (3)	0.69386 (11)	0.78892 (14)	0.0335 (4)
H93	−0.2303	0.7427	0.8211	0.034 (7)*
O2	0.9374 (3)	0.91779 (11)	0.81113 (14)	0.0316 (4)
O3	0.6734 (2)	0.84425 (12)	0.88161 (12)	0.0279 (3)
C1	0.3185 (3)	0.84770 (18)	1.08632 (14)	0.0202 (3)
C2	0.1952 (4)	0.92054 (14)	1.11836 (18)	0.0235 (4)
H2	0.0400	0.9306	1.0956	0.028*
C3	0.3518 (4)	0.97480 (13)	1.19111 (18)	0.0260 (5)
H3	0.3165	1.0267	1.2243	0.031*
C4	0.5715 (4)	0.93652 (14)	1.20475 (18)	0.0243 (4)
H4	0.7044	0.9587	1.2487	0.029*
C5	0.5524 (3)	0.85864 (18)	1.13951 (15)	0.0209 (4)
H5	0.6712	0.8211	1.1324	0.025*
C6	0.2180 (4)	0.73848 (15)	1.30972 (19)	0.0322 (5)
H6	0.1563	0.6940	1.2603	0.039*
C7	0.0964 (4)	0.80938 (16)	1.3456 (2)	0.0319 (5)
H7	−0.0592	0.8194	1.3245	0.038*
C8	0.2551 (4)	0.86256 (18)	1.41971 (17)	0.0302 (5)
H8	0.2219	0.9138	1.4551	0.036*
C9	0.4725 (4)	0.82358 (14)	1.42989 (18)	0.0297 (5)
H9	0.6072	0.8445	1.4736	0.036*
C10	0.4491 (4)	0.74712 (15)	1.36194 (19)	0.0301 (5)
H10	0.5659	0.7091	1.3532	0.036*
C11	0.2253 (4)	0.77346 (13)	1.01152 (17)	0.0220 (4)
H11A	0.0684	0.7634	1.0190	0.026*
H11B	0.3118	0.7214	1.0368	0.026*
C12	0.2090 (4)	0.71216 (13)	0.80983 (17)	0.0211 (4)
H12	0.3477	0.6771	0.8297	0.025*
C13	0.0092 (4)	0.65595 (13)	0.82677 (19)	0.0242 (4)
H13A	0.0162	0.6017	0.7857	0.029*
H13B	0.0245	0.6423	0.9083	0.029*
C14	0.1931 (4)	0.74385 (14)	0.68492 (18)	0.0255 (4)
H14A	0.0653	0.7834	0.6659	0.031*
H14B	0.3305	0.7756	0.6785	0.031*
C15	0.1632 (4)	0.66929 (13)	0.59961 (17)	0.0220 (4)
C16	0.3474 (4)	0.61840 (14)	0.58549 (18)	0.0261 (5)
H16	0.4909	0.6307	0.6280	0.031*
C17	0.3201 (4)	0.54932 (15)	0.5087 (2)	0.0307 (5)
H17	0.4447	0.5151	0.5009	0.037*
C18	0.1077 (5)	0.53108 (15)	0.4434 (2)	0.0304 (5)
H18	0.0896	0.4851	0.3912	0.037*
C19	−0.0769 (4)	0.58170 (15)	0.45646 (19)	0.0294 (5)
H19	−0.2199	0.5700	0.4129	0.035*
C20	−0.0487 (4)	0.65025 (15)	0.53490 (19)	0.0258 (5)
H20	−0.1739	0.6837	0.5440	0.031*
C21	0.7467 (4)	0.91227 (15)	0.83988 (18)	0.0259 (4)
C22	0.6023 (5)	0.99310 (18)	0.8262 (2)	0.0466 (7)
H22	0.6189	1.0309	0.7667	0.056*
C23	0.4576 (5)	1.01401 (17)	0.8904 (2)	0.0474 (7)
H23	0.4445	0.9754	0.9496	0.057*
C24	0.3080 (5)	1.09256 (16)	0.8816 (3)	0.0422 (6)
H24A	0.3545	1.1333	0.8287	0.063*
H24B	0.3207	1.1190	0.9563	0.063*
H24C	0.1528	1.0757	0.8541	0.063*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.02130 (13)	0.02038 (12)	0.01725 (12)	0.00067 (14)	0.00270 (9)	0.00026 (14)
N1	0.0175 (9)	0.0220 (8)	0.0167 (8)	−0.0016 (7)	0.0030 (6)	−0.0008 (6)
O1	0.0226 (8)	0.0361 (9)	0.0408 (9)	−0.0039 (7)	0.0033 (7)	−0.0117 (7)
O2	0.0224 (8)	0.0355 (9)	0.0386 (9)	0.0020 (7)	0.0104 (7)	0.0121 (7)
O3	0.0221 (7)	0.0293 (8)	0.0337 (7)	0.0016 (8)	0.0089 (5)	0.0043 (8)
C1	0.0221 (8)	0.0229 (9)	0.0153 (7)	0.0016 (11)	0.0027 (6)	0.0010 (10)
C2	0.0229 (11)	0.0263 (10)	0.0206 (10)	0.0053 (8)	0.0020 (8)	0.0042 (8)
C3	0.0335 (12)	0.0196 (10)	0.0245 (11)	0.0028 (9)	0.0042 (9)	0.0014 (8)
C4	0.0244 (11)	0.0250 (11)	0.0235 (10)	−0.0048 (8)	0.0041 (8)	−0.0013 (8)
C5	0.0202 (9)	0.0226 (9)	0.0204 (8)	0.0010 (10)	0.0046 (7)	0.0029 (10)
C6	0.0433 (14)	0.0284 (11)	0.0238 (11)	−0.0115 (10)	0.0031 (10)	0.0039 (9)
C7	0.0259 (12)	0.0436 (13)	0.0277 (12)	−0.0029 (10)	0.0086 (9)	0.0068 (10)
C8	0.0413 (12)	0.0327 (13)	0.0195 (9)	0.0010 (11)	0.0131 (8)	0.0008 (10)
C9	0.0325 (12)	0.0380 (13)	0.0171 (10)	−0.0031 (9)	0.0005 (9)	0.0027 (8)
C10	0.0389 (13)	0.0278 (11)	0.0228 (11)	0.0075 (10)	0.0038 (9)	0.0069 (9)
C11	0.0266 (11)	0.0232 (10)	0.0162 (9)	−0.0033 (8)	0.0039 (8)	0.0018 (8)
C12	0.0226 (10)	0.0219 (10)	0.0187 (10)	−0.0024 (8)	0.0037 (8)	−0.0022 (8)
C13	0.0233 (11)	0.0255 (11)	0.0241 (10)	−0.0038 (8)	0.0051 (8)	−0.0030 (8)
C14	0.0299 (12)	0.0243 (10)	0.0217 (10)	−0.0019 (9)	0.0033 (9)	0.0004 (8)
C15	0.0273 (11)	0.0240 (10)	0.0147 (9)	−0.0031 (9)	0.0034 (8)	0.0020 (8)
C16	0.0236 (11)	0.0298 (11)	0.0242 (11)	0.0000 (9)	0.0023 (9)	0.0044 (9)
C17	0.0309 (13)	0.0296 (12)	0.0337 (12)	0.0046 (9)	0.0114 (10)	0.0034 (10)
C18	0.0430 (16)	0.0248 (12)	0.0244 (11)	−0.0063 (10)	0.0085 (10)	−0.0012 (9)
C19	0.0292 (13)	0.0349 (12)	0.0228 (11)	−0.0055 (10)	0.0013 (9)	0.0005 (9)
C20	0.0246 (12)	0.0304 (12)	0.0216 (11)	0.0020 (10)	0.0026 (9)	0.0014 (9)
C21	0.0241 (11)	0.0303 (11)	0.0234 (10)	0.0041 (9)	0.0043 (9)	0.0058 (9)
C22	0.0508 (17)	0.0441 (15)	0.0521 (16)	0.0222 (13)	0.0286 (13)	0.0257 (13)
C23	0.064 (2)	0.0370 (14)	0.0464 (16)	0.0139 (13)	0.0238 (14)	0.0131 (12)
C24	0.0431 (16)	0.0321 (13)	0.0530 (16)	0.0061 (11)	0.0133 (13)	0.0033 (12)

Geometric parameters (Å, º) top

Fe1—C1	2.0271 (17)	C9—H9	0.9300
Fe1—C10	2.040 (2)	C10—H10	0.9300
Fe1—C2	2.041 (2)	C11—H11A	0.9700
Fe1—C5	2.0430 (18)	C11—H11B	0.9700
Fe1—C6	2.043 (2)	C12—C13	1.516 (3)
Fe1—C9	2.047 (2)	C12—C14	1.536 (3)
Fe1—C8	2.0533 (19)	C12—H12	0.9800
Fe1—C4	2.053 (2)	C13—H13A	0.9700
Fe1—C3	2.054 (2)	C13—H13B	0.9700
Fe1—C7	2.059 (2)	C14—C15	1.514 (3)
N1—C11	1.506 (2)	C14—H14A	0.9700
N1—C12	1.507 (2)	C14—H14B	0.9700
N1—H91	0.9454	C15—C16	1.385 (3)
N1—H92	0.8195	C15—C20	1.385 (3)
O1—C13	1.407 (3)	C16—C17	1.386 (3)
O1—H93	0.8666	C16—H16	0.9300
C1—C2	1.429 (3)	C17—C18	1.387 (4)
C1—C5	1.433 (3)	C17—H17	0.9300
C1—C11	1.487 (3)	C18—C19	1.381 (3)
C2—C3	1.419 (3)	C18—H18	0.9300
C2—H2	0.9300	C19—C20	1.392 (3)
C3—C4	1.420 (3)	C19—H19	0.9300
C3—H3	0.9300	C20—H20	0.9300
C4—C5	1.417 (3)	O2—C21	1.249 (3)
C4—H4	0.9300	O3—C21	1.268 (3)
C5—H5	0.9300	C21—C22	1.505 (3)
C6—C10	1.411 (3)	C22—C23	1.288 (4)
C6—C7	1.417 (3)	C22—H22	0.9300
C6—H6	0.9300	C23—C24	1.496 (3)
C7—C8	1.424 (3)	C23—H23	0.9300
C7—H7	0.9300	C24—H24A	0.9600
C8—C9	1.415 (3)	C24—H24B	0.9600
C8—H8	0.9300	C24—H24C	0.9600
C9—C10	1.415 (3)

C1—Fe1—C10	121.63 (10)	C10—C6—H6	125.9
C1—Fe1—C2	41.13 (9)	C7—C6—H6	125.9
C10—Fe1—C2	158.18 (9)	Fe1—C6—H6	125.6
C1—Fe1—C5	41.24 (7)	C6—C7—C8	107.7 (2)
C10—Fe1—C5	106.98 (10)	C6—C7—Fe1	69.19 (13)
C2—Fe1—C5	68.83 (8)	C8—C7—Fe1	69.54 (12)
C1—Fe1—C6	106.79 (10)	C6—C7—H7	126.1
C10—Fe1—C6	40.44 (10)	C8—C7—H7	126.1
C2—Fe1—C6	122.59 (9)	Fe1—C7—H7	126.7
C5—Fe1—C6	122.90 (10)	C9—C8—C7	107.8 (2)
C1—Fe1—C9	157.79 (9)	C9—C8—Fe1	69.58 (12)
C10—Fe1—C9	40.52 (9)	C7—C8—Fe1	69.93 (12)
C2—Fe1—C9	159.87 (9)	C9—C8—H8	126.1
C5—Fe1—C9	121.99 (9)	C7—C8—H8	126.1
C6—Fe1—C9	68.08 (9)	Fe1—C8—H8	126.0
C1—Fe1—C8	159.80 (8)	C8—C9—C10	108.1 (2)
C10—Fe1—C8	68.07 (10)	C8—C9—Fe1	70.04 (12)
C2—Fe1—C8	123.80 (9)	C10—C9—Fe1	69.47 (12)
C5—Fe1—C8	158.01 (9)	C8—C9—H9	126.0
C6—Fe1—C8	68.15 (10)	C10—C9—H9	126.0
C9—Fe1—C8	40.38 (9)	Fe1—C9—H9	126.1
C1—Fe1—C4	68.90 (9)	C6—C10—C9	108.2 (2)
C10—Fe1—C4	123.05 (10)	C6—C10—Fe1	69.89 (12)
C2—Fe1—C4	68.52 (9)	C9—C10—Fe1	70.01 (12)
C5—Fe1—C4	40.47 (10)	C6—C10—H10	125.9
C6—Fe1—C4	159.02 (9)	C9—C10—H10	125.9
C9—Fe1—C4	107.71 (9)	Fe1—C10—H10	125.8
C8—Fe1—C4	122.89 (10)	C1—C11—N1	111.13 (16)
C1—Fe1—C3	68.67 (10)	C1—C11—H11A	109.4
C10—Fe1—C3	159.57 (9)	N1—C11—H11A	109.4
C2—Fe1—C3	40.55 (9)	C1—C11—H11B	109.4
C5—Fe1—C3	68.13 (10)	N1—C11—H11B	109.4
C6—Fe1—C3	158.90 (9)	H11A—C11—H11B	108.0
C9—Fe1—C3	123.88 (9)	N1—C12—C13	112.49 (16)
C8—Fe1—C3	108.60 (10)	N1—C12—C14	107.53 (15)
C4—Fe1—C3	40.47 (9)	C13—C12—C14	113.21 (17)
C1—Fe1—C7	123.06 (9)	N1—C12—H12	107.8
C10—Fe1—C7	67.96 (10)	C13—C12—H12	107.8
C2—Fe1—C7	108.04 (10)	C14—C12—H12	107.8
C5—Fe1—C7	159.48 (9)	O1—C13—C12	114.61 (17)
C6—Fe1—C7	40.43 (10)	O1—C13—H13A	108.6
C9—Fe1—C7	67.97 (9)	C12—C13—H13A	108.6
C8—Fe1—C7	40.53 (10)	O1—C13—H13B	108.6
C4—Fe1—C7	158.99 (9)	C12—C13—H13B	108.6
C3—Fe1—C7	123.54 (10)	H13A—C13—H13B	107.6
C11—N1—C12	114.96 (15)	C12—C14—C15	111.95 (17)
C11—N1—H91	106.0	C15—C14—H14A	109.2
C12—N1—H91	111.0	C12—C14—H14A	109.2
C11—N1—H92	105.9	C15—C14—H14B	109.2
C12—N1—H92	109.2	C12—C14—H14B	109.2
H91—N1—H92	109.5	H14A—C14—H14B	107.9
C13—O1—H93	116.1	C16—C15—C20	118.7 (2)
C2—C1—C5	107.5 (2)	C16—C15—C14	120.54 (19)
C2—C1—C11	127.15 (18)	C20—C15—C14	120.7 (2)
C5—C1—C11	125.4 (2)	C15—C16—C17	120.7 (2)
C2—C1—Fe1	69.96 (11)	C15—C16—H16	119.6
C5—C1—Fe1	69.98 (9)	C17—C16—H16	119.6
C11—C1—Fe1	125.48 (16)	C16—C17—C18	120.2 (2)
C3—C2—C1	107.84 (18)	C16—C17—H17	119.9
C3—C2—Fe1	70.21 (12)	C18—C17—H17	119.9
C1—C2—Fe1	68.91 (11)	C19—C18—C17	119.5 (2)
C3—C2—H2	126.1	C19—C18—H18	120.3
C1—C2—H2	126.1	C17—C18—H18	120.3
Fe1—C2—H2	126.4	C18—C19—C20	119.9 (2)
C2—C3—C4	108.53 (18)	C18—C19—H19	120.0
C2—C3—Fe1	69.24 (12)	C20—C19—H19	120.0
C4—C3—Fe1	69.75 (12)	C15—C20—C19	120.9 (2)
C2—C3—H3	125.7	C15—C20—H20	119.6
C4—C3—H3	125.7	C19—C20—H20	119.6
Fe1—C3—H3	126.9	O2—C21—O3	123.9 (2)
C5—C4—C3	107.96 (19)	O2—C21—C22	116.6 (2)
C5—C4—Fe1	69.37 (12)	O3—C21—C22	119.5 (2)
C3—C4—Fe1	69.79 (12)	C23—C22—C21	125.2 (2)
C5—C4—H4	126.0	C23—C22—H22	117.4
C3—C4—H4	126.0	C21—C22—H22	117.4
Fe1—C4—H4	126.4	C22—C23—C24	128.1 (3)
C4—C5—C1	108.2 (2)	C22—C23—H23	115.9
C4—C5—Fe1	70.16 (11)	C24—C23—H23	115.9
C1—C5—Fe1	68.79 (10)	C23—C24—H24A	109.5
C4—C5—H5	125.9	C23—C24—H24B	109.5
C1—C5—H5	125.9	H24A—C24—H24B	109.5
Fe1—C5—H5	126.7	C23—C24—H24C	109.5
C10—C6—C7	108.2 (2)	H24A—C24—H24C	109.5
C10—C6—Fe1	69.67 (13)	H24B—C24—H24C	109.5
C7—C6—Fe1	70.37 (13)

C10—Fe1—C1—C2	162.25 (13)	C4—Fe1—C6—C10	44.6 (3)
C5—Fe1—C1—C2	−118.3 (2)	C3—Fe1—C6—C10	−166.5 (2)
C6—Fe1—C1—C2	120.65 (14)	C7—Fe1—C6—C10	−119.01 (19)
C9—Fe1—C1—C2	−166.4 (2)	C1—Fe1—C6—C7	−121.63 (14)
C8—Fe1—C1—C2	48.5 (4)	C10—Fe1—C6—C7	119.01 (19)
C4—Fe1—C1—C2	−81.09 (14)	C2—Fe1—C6—C7	−79.43 (15)
C3—Fe1—C1—C2	−37.53 (13)	C5—Fe1—C6—C7	−163.87 (13)
C7—Fe1—C1—C2	79.43 (17)	C9—Fe1—C6—C7	81.30 (15)
C10—Fe1—C1—C5	−79.49 (18)	C8—Fe1—C6—C7	37.63 (13)
C2—Fe1—C1—C5	118.3 (2)	C4—Fe1—C6—C7	163.6 (2)
C6—Fe1—C1—C5	−121.09 (16)	C3—Fe1—C6—C7	−47.5 (3)
C9—Fe1—C1—C5	−48.1 (3)	C10—C6—C7—C8	0.6 (2)
C8—Fe1—C1—C5	166.7 (3)	Fe1—C6—C7—C8	−59.06 (16)
C4—Fe1—C1—C5	37.17 (15)	C10—C6—C7—Fe1	59.66 (15)
C3—Fe1—C1—C5	80.73 (16)	C1—Fe1—C7—C6	76.56 (17)
C7—Fe1—C1—C5	−162.31 (14)	C10—Fe1—C7—C6	−37.74 (14)
C10—Fe1—C1—C11	40.3 (2)	C2—Fe1—C7—C6	119.41 (14)
C2—Fe1—C1—C11	−122.0 (2)	C5—Fe1—C7—C6	41.7 (3)
C5—Fe1—C1—C11	119.8 (3)	C9—Fe1—C7—C6	−81.61 (14)
C6—Fe1—C1—C11	−1.3 (2)	C8—Fe1—C7—C6	−119.3 (2)
C9—Fe1—C1—C11	71.7 (3)	C4—Fe1—C7—C6	−163.7 (2)
C8—Fe1—C1—C11	−73.5 (4)	C3—Fe1—C7—C6	161.43 (13)
C4—Fe1—C1—C11	156.9 (2)	C1—Fe1—C7—C8	−164.13 (15)
C3—Fe1—C1—C11	−159.50 (19)	C10—Fe1—C7—C8	81.57 (16)
C7—Fe1—C1—C11	−42.5 (2)	C2—Fe1—C7—C8	−121.28 (15)
C5—C1—C2—C3	−0.5 (2)	C5—Fe1—C7—C8	161.0 (2)
C11—C1—C2—C3	179.57 (19)	C6—Fe1—C7—C8	119.3 (2)
Fe1—C1—C2—C3	59.65 (15)	C9—Fe1—C7—C8	37.70 (14)
C5—C1—C2—Fe1	−60.19 (13)	C4—Fe1—C7—C8	−44.4 (3)
C11—C1—C2—Fe1	119.9 (2)	C3—Fe1—C7—C8	−79.26 (17)
C1—Fe1—C2—C3	−119.19 (18)	C6—C7—C8—C9	−0.6 (2)
C10—Fe1—C2—C3	−163.5 (2)	Fe1—C7—C8—C9	−59.48 (14)
C5—Fe1—C2—C3	−80.69 (14)	C6—C7—C8—Fe1	58.85 (15)
C6—Fe1—C2—C3	162.97 (13)	C1—Fe1—C8—C9	160.5 (3)
C9—Fe1—C2—C3	45.8 (3)	C10—Fe1—C8—C9	37.68 (14)
C8—Fe1—C2—C3	78.92 (16)	C2—Fe1—C8—C9	−163.12 (13)
C4—Fe1—C2—C3	−37.10 (13)	C5—Fe1—C8—C9	−43.3 (4)
C7—Fe1—C2—C3	120.86 (14)	C6—Fe1—C8—C9	81.42 (15)
C10—Fe1—C2—C1	−44.3 (3)	C4—Fe1—C8—C9	−78.40 (17)
C5—Fe1—C2—C1	38.51 (13)	C3—Fe1—C8—C9	−120.82 (14)
C6—Fe1—C2—C1	−77.83 (15)	C7—Fe1—C8—C9	119.0 (2)
C9—Fe1—C2—C1	165.0 (2)	C1—Fe1—C8—C7	41.6 (4)
C8—Fe1—C2—C1	−161.88 (13)	C10—Fe1—C8—C7	−81.28 (16)
C4—Fe1—C2—C1	82.10 (13)	C2—Fe1—C8—C7	77.92 (18)
C3—Fe1—C2—C1	119.19 (18)	C5—Fe1—C8—C7	−162.3 (3)
C7—Fe1—C2—C1	−119.94 (13)	C6—Fe1—C8—C7	−37.54 (15)
C1—C2—C3—C4	0.0 (2)	C9—Fe1—C8—C7	−119.0 (2)
Fe1—C2—C3—C4	58.83 (15)	C4—Fe1—C8—C7	162.64 (14)
C1—C2—C3—Fe1	−58.83 (14)	C3—Fe1—C8—C7	120.22 (15)
C1—Fe1—C3—C2	38.06 (12)	C7—C8—C9—C10	0.4 (2)
C10—Fe1—C3—C2	162.4 (2)	Fe1—C8—C9—C10	−59.28 (15)
C5—Fe1—C3—C2	82.56 (13)	C7—C8—C9—Fe1	59.70 (15)
C6—Fe1—C3—C2	−43.3 (3)	C1—Fe1—C9—C8	−162.3 (2)
C9—Fe1—C3—C2	−162.72 (13)	C10—Fe1—C9—C8	−119.2 (2)
C8—Fe1—C3—C2	−120.63 (13)	C2—Fe1—C9—C8	44.5 (3)
C4—Fe1—C3—C2	120.14 (18)	C5—Fe1—C9—C8	162.37 (16)
C7—Fe1—C3—C2	−78.28 (15)	C6—Fe1—C9—C8	−81.59 (16)
C1—Fe1—C3—C4	−82.08 (13)	C4—Fe1—C9—C8	120.28 (15)
C10—Fe1—C3—C4	42.3 (3)	C3—Fe1—C9—C8	78.66 (17)
C2—Fe1—C3—C4	−120.14 (18)	C7—Fe1—C9—C8	−37.84 (15)
C5—Fe1—C3—C4	−37.58 (12)	C1—Fe1—C9—C10	−43.1 (3)
C6—Fe1—C3—C4	−163.4 (2)	C2—Fe1—C9—C10	163.7 (2)
C9—Fe1—C3—C4	77.14 (15)	C5—Fe1—C9—C10	−78.40 (16)
C8—Fe1—C3—C4	119.22 (13)	C6—Fe1—C9—C10	37.63 (14)
C7—Fe1—C3—C4	161.58 (13)	C8—Fe1—C9—C10	119.2 (2)
C2—C3—C4—C5	0.5 (2)	C4—Fe1—C9—C10	−120.49 (14)
Fe1—C3—C4—C5	59.07 (15)	C3—Fe1—C9—C10	−162.11 (14)
C2—C3—C4—Fe1	−58.52 (15)	C7—Fe1—C9—C10	81.39 (15)
C1—Fe1—C4—C5	−37.85 (13)	C7—C6—C10—C9	−0.3 (2)
C10—Fe1—C4—C5	76.95 (15)	Fe1—C6—C10—C9	59.76 (15)
C2—Fe1—C4—C5	−82.15 (13)	C7—C6—C10—Fe1	−60.10 (15)
C6—Fe1—C4—C5	44.0 (3)	C8—C9—C10—C6	−0.1 (2)
C9—Fe1—C4—C5	118.85 (13)	Fe1—C9—C10—C6	−59.68 (15)
C8—Fe1—C4—C5	160.63 (13)	C8—C9—C10—Fe1	59.63 (15)
C3—Fe1—C4—C5	−119.32 (18)	C1—Fe1—C10—C6	−78.49 (15)
C7—Fe1—C4—C5	−166.6 (2)	C2—Fe1—C10—C6	−45.8 (3)
C1—Fe1—C4—C3	81.46 (14)	C5—Fe1—C10—C6	−121.15 (14)
C10—Fe1—C4—C3	−163.74 (12)	C9—Fe1—C10—C6	119.15 (19)
C2—Fe1—C4—C3	37.17 (12)	C8—Fe1—C10—C6	81.60 (15)
C5—Fe1—C4—C3	119.32 (18)	C4—Fe1—C10—C6	−162.53 (13)
C6—Fe1—C4—C3	163.3 (2)	C3—Fe1—C10—C6	166.1 (2)
C9—Fe1—C4—C3	−121.83 (13)	C7—Fe1—C10—C6	37.73 (14)
C8—Fe1—C4—C3	−80.05 (15)	C1—Fe1—C10—C9	162.36 (13)
C7—Fe1—C4—C3	−47.3 (3)	C2—Fe1—C10—C9	−165.0 (2)
C3—C4—C5—C1	−0.9 (2)	C5—Fe1—C10—C9	119.70 (14)
Fe1—C4—C5—C1	58.45 (14)	C6—Fe1—C10—C9	−119.15 (19)
C3—C4—C5—Fe1	−59.33 (15)	C8—Fe1—C10—C9	−37.56 (14)
C2—C1—C5—C4	0.9 (2)	C4—Fe1—C10—C9	78.31 (16)
C11—C1—C5—C4	−179.22 (19)	C3—Fe1—C10—C9	46.9 (3)
Fe1—C1—C5—C4	−59.30 (14)	C7—Fe1—C10—C9	−81.43 (15)
C2—C1—C5—Fe1	60.18 (13)	C2—C1—C11—N1	91.1 (2)
C11—C1—C5—Fe1	−119.9 (2)	C5—C1—C11—N1	−88.8 (2)
C1—Fe1—C5—C4	119.7 (2)	Fe1—C1—C11—N1	−178.21 (13)
C10—Fe1—C5—C4	−121.38 (14)	C12—N1—C11—C1	163.62 (17)
C2—Fe1—C5—C4	81.30 (14)	C11—N1—C12—C13	47.3 (2)
C6—Fe1—C5—C4	−162.76 (13)	C11—N1—C12—C14	172.66 (17)
C9—Fe1—C5—C4	−79.66 (16)	N1—C12—C13—O1	68.3 (2)
C8—Fe1—C5—C4	−48.1 (3)	C14—C12—C13—O1	−53.8 (2)
C3—Fe1—C5—C4	37.57 (13)	N1—C12—C14—C15	−179.54 (17)
C7—Fe1—C5—C4	166.3 (2)	C13—C12—C14—C15	−54.7 (2)
C10—Fe1—C5—C1	118.91 (16)	C12—C14—C15—C16	−78.0 (2)
C2—Fe1—C5—C1	−38.41 (15)	C12—C14—C15—C20	101.5 (2)
C6—Fe1—C5—C1	77.52 (17)	C20—C15—C16—C17	−0.4 (3)
C9—Fe1—C5—C1	160.63 (15)	C14—C15—C16—C17	179.08 (19)
C8—Fe1—C5—C1	−167.8 (3)	C15—C16—C17—C18	1.0 (3)
C4—Fe1—C5—C1	−119.7 (2)	C16—C17—C18—C19	−0.7 (3)
C3—Fe1—C5—C1	−82.14 (16)	C17—C18—C19—C20	−0.1 (4)
C7—Fe1—C5—C1	46.6 (3)	C16—C15—C20—C19	−0.4 (3)
C1—Fe1—C6—C10	119.37 (13)	C14—C15—C20—C19	−179.93 (19)
C2—Fe1—C6—C10	161.56 (13)	C18—C19—C20—C15	0.7 (4)
C5—Fe1—C6—C10	77.12 (15)	O2—C21—C22—C23	−149.0 (3)
C9—Fe1—C6—C10	−37.71 (13)	O3—C21—C22—C23	29.3 (4)
C8—Fe1—C6—C10	−81.38 (14)	C21—C22—C23—C24	−179.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H91···O2ⁱ	0.95	1.74	2.685 (2)	173
N1—H92···O3	0.82	1.94	2.747 (2)	170
O1—H93···O3ⁱ	0.87	1.85	2.712 (2)	172
C16—H16···O1ⁱⁱ	0.93	2.56	3.447 (3)	159
C18—H18···O2ⁱⁱⁱ	0.93	2.58	3.435 (3)	154

Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) −x+1, y−1/2, −z+1.

Experimental details

Crystal data
Chemical formula	[Fe(C₅H₅)(C₁₅H₁₉NO)](C₄H₅O₂)
M_r	435.33
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	150
a, b, c (Å)	5.9730 (2), 15.3905 (3), 11.7713 (4)
β (°)	100.4986 (13)
V (Å³)	1063.99 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.73
Crystal size (mm)	0.33 × 0.12 × 0.10

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	15916, 4864, 4511
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.067, 1.05
No. of reflections	4864
No. of parameters	265
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.27
Absolute structure	Flack (1983), 2329 Friedel pairs
Absolute structure parameter	−0.016 (12)

Computer programs: COLLECT (Nonius, 2000), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H91···O2ⁱ	0.95	1.74	2.685 (2)	173
N1—H92···O3	0.82	1.94	2.747 (2)	170
O1—H93···O3ⁱ	0.87	1.85	2.712 (2)	172
C16—H16···O1ⁱⁱ	0.93	2.56	3.447 (3)	159
C18—H18···O2ⁱⁱⁱ	0.93	2.58	3.435 (3)	154

Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) −x+1, y−1/2, −z+1.

Acknowledgements

This work was supported financially by the Ministry of Education, Youth and Sports of the Czech Republic as a part of the long-term research project No. MSM0021620857.

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
Braga, D., Curzi, M., Giaffreda, S. L., Grepioni, F., Maini, L., Pettersen, A. & Polito, M. (2008). Ferrocenes: Ligands, Materials and Biomolecules, edited by P. Štěpnička, pp. 465–498, Chichester: Wiley. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Hess, A., Brosch, O., Weyhermüller, T. & Metzler-Nolte, N. (1999). J. Organomet. Chem. 589, 75–84. Web of Science CSD CrossRef CAS Google Scholar
Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Štěpnička, P., Císařová, I. & Ludvík, J. (2004). J. Organomet. Chem. 689, 631–638. Google Scholar
Štěpnička, P., Zábranský, M., Císařová, I. & Lamač, M. (2008a). J. Organomet. Chem. 693, 3831–3841. Google Scholar
Štěpnička, P., Zábranský, M., Lamač, M., Císařová, I. & Němec, P. (2008b). J. Organomet. Chem. 693, 1779–1786. Google Scholar

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Volume 67| Part 11| November 2011| Pages m1619-m1620

doi:10.1107/S1600536811044096

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(R)-N-(Ferrocenylmeth­yl)-1-hy­dr­oxy-3-phenyl­propan-2-aminium (E)-but-2-enoate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

(R)-N-(Ferrocenylmethyl)-1-hydroxy-3-phenylpropan-2-aminium (E)-but-2-enoate