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In the title compound, [Fe(C5H5)(C12H19NO)]I, the ferrocene moiety has an eclipsed conformation, with mean Fe—C bond lengths of 2.031 (4) and 2.020 (6) Å for the substituted and unsubstituted cyclo­penta­dienyl rings. The pyrrolidinium heterocycle adopts an envelope conformation and has its 1- and 2-substituents in a relative trans disposition. Strong (+/−)-charge-assisted N—H...I and C—H...I hydrogen bonds are present. The crystal structure is also stabilized by weak C—H...O interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270104027581/fa1094sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270104027581/fa1094Isup2.hkl
Contains datablock I

CCDC reference: 263033

Comment top

(S)-2-(Methoxymethyl)-1-ferrocenylmethyl-pyrrolidine, (Ia), is a useful starting material for the synthesis of enantiomerically pure chiral ferrocenes, which are important for asymmetric catalysis (Ganter & Wagner, 1995). Since (Ia) is an oil, it could not be characterized by X-ray diffraction. However, we have found that the corresponding hydroiodide, (I), forms crystals suitable for crystallographic study. We report here the structure of (I), revealing the absolute configuration at the N atom and intermolecular hydrogen bonds influencing the crystal packing.

In (I), the cyclopentadienyl rings in the ferrocene moiety (substituted CpA and unsubstitued CpB) are parallel [dihedral angle = 1.5 (2)°]. The Cp rings are essentially eclipsed, with CnA—CgA—CgB—CnB angles (n = 1–5; CgA and CgB are the centroids of the corresponding Cp rings) averaging approximately 3°. The Fe—CgA and Fe—CgB distances are 1.6423 (4) and 1.6464 (4) Å, respectively, and the CgA—Fe—CgB angle is 179.2 (2)°. The small but systematic differences between the Fe—CnA bond lengths [2.024 (3)–2.040 (4) Å], and the shorter corresponding Fe—CnB distances, [2.011 (4)–2.026 (7) Å], as well as the slight differences between the observed C—C distances in the two rings, could be the result of greater overall displacement, including libration, for ring CpB. Methine atom C6 is tilted slightly from the plane of its carrier Cp ring, toward the Fe atom. The C1A—C6 bond forms an angle of 3.4 (2)° with the plane of ring CpA, while the Fe···C6 distance is 3.090 (4) Å. The C6—N7 bond is in an antiperiplanar orientation with respect to the ferrocene moiety [Fe—C1A—C6—N7 = 176.3 (2)°].

The five-membered heterocyclic ring adopts an envelope conformation with atom C8 at the apex. The ring puckering parameters (Cremer & Pople, 1975) for the N7/C8–C11 ring are q2 = 0.307 (4) Å and ϕ2 = −147.0 (7)°. The corresponding asymmetry parameter (Nardelli, 1983) ΔS (C8) is 0.013 (2). The flat fragment of this ring, C9/C10/C11/N7, forms an angle of 41.2 (2)° with the plane of ring CpA. The substituents at atoms N7 and C8 are equatorial and in a relative trans disposition. Torsion angles describing these features are presented in Table 1.

The molecule has two chiral centers, N7 and C8, and crystallizes in a chiral space group. The Flack (1983) parameter was refined, revealing the stereochemistry 1R(N7),2S(C8) (Fig. 1). Thus protonation of the N atom in (Ia) proceeded in a diastereoselective manner, leading to the more stable trans arrangement of substituents at atoms N7 and C8.

Hydrogen bonding is important in the extended structure of (I). Table 2 collects all interactions with H···A distances shorter than the sum of the van der Waals radii (Bondi, 1964) minus 0.1 Å. There are three interactions in which the iodine anion acts as an acceptor, while the positively charged atom N7 and two of the C atoms bonded to it (C6 and C8) act as donors.

The N7—H7···Ii [symmetry code: (i) −1 + x, y, z] contact is an example of a charge-assisted hydrogen bond in which the donor and acceptor are oppositely charged ions [(+/-)CAHB]. This type of interaction, also called a salt bridge (Gilli & Gilli, 2000), is the strongest known hydrogen-bond type. There are 1453 cases of N—H···I hydrogen bonds in the Cambridge Structural Database (CSD; Version of November 2003; Allen, 2002), of which only about 14% (201 cases) may be classified as (+/-)CAHB. The average (N)H···I distance is 2.958 Å for N—H···I hydrogen bonding without charge assistance, and 2.899 Å for (+)CAHB, 2.855 Å for (-)CAHB and 2.808 Å for (+/-)CAHB. These differences in hydrogen-bond lengths are unsurprizing, since the proton–acceptor distance correlates well with hydrogen-bond energy (Grabowski, 2003) and is often applied as a criterion for judging hydrogen-bond strength. On the basis of this distance, the N—H···I interaction in (I) may be considered to be relatively strong compared with all of the N—H···I (+/-)CAHB iteractions found in the CSD. There are also two C—H···I interactions in (I), with atoms C6 and C8 acting as donors. It is known that Csp3 atoms have limited proton-donating properties (Desiragu & Steiner, 1999), but in this case proximity to the positively charged N atom may enhance the capacity of atoms C6 and C8 to take part in hydrogen bonding. These weaker interactions complete a six-membered ring, with second-level graph-set descriptor R21(6) (Bernstein et al., 1995), while the first-level graph-set descriptor, C(6), describes chains generated from a translation operation along [100], as shown in Fig. 2.

The crystal packing of (I) is also stabilized by weak C—H···O interactions. In one of these, C10—H102···O82ii [symmetry code: (ii) −x, 0.5 + y, 0.5 − z], the molecules are related by a 21 symmetry operation, which leads to formation of C(6) chains. A short H61···O82 distance suggests the existence of a further intermolecular interaction, C6—H61···O82, graph set S(6). In sum there is a three-dimensional network of hydrogen bonds of varying strength, which stabilizes the hydroiodide moiety in the crystal.

Experimental top

The iodide salt was generated by reaction of (S)-2-(methoxymethyl)-1-ferrocenylmethylpyrrolidine (Ganter & Wagner, 1995) with hydriodic acid in acetone at 0° [273 K?] for 1 h. X ray-quality single crystals were obtained from a diethyl ether solution cooled at 5° [278 K?].

Refinement top

All H atoms were placed in idealized positions and constrained to ride on their parent atoms, with C—H distances in the range 0.93–0.98 Å, an N—H distance of 0.91 Å and Uiso(H) = 1.2Ueq(C,N).

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1989); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PARST (Nardelli, 1996).

Figures top
[Figure 1] Fig. 1. A view of (I) (40% probability displacement ellipsoids).
[Figure 2] Fig. 2. Charge-assisted hydrogen bonding in (I). The molecules form chains along the [100] direction.
(1R,2S)-2-methoxymethyl-1-(ferrocenylmethyl)pyrrolidinium iodide top
Crystal data top
[Fe(C5H5)(C12H19NO)]IF(000) = 880
Mr = 441.12Dx = 1.615 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 25 reflections
a = 7.777 (2) Åθ = 12.7–14.9°
b = 11.575 (3) ŵ = 2.53 mm1
c = 20.160 (5) ÅT = 293 K
V = 1814.8 (8) Å3Needle, orange
Z = 40.5 × 0.1 × 0.1 mm
Data collection top
Rigaku AFC-5S
diffractometer
θmax = 26°, θmin = 3.2°
Graphite monochromatorh = 99
ω scank = 1414
14192 measured reflectionsl = 2424
3559 independent reflections3 standard reflections every 150 reflections
2211 reflections with I > 2σ(I) intensity decay: 2%
Rint = 0.051
Refinement top
Refinement on F2H-atom parameters constrained
Least-squares matrix: full w = 1/[σ2(Fo2) + (0.0149P)2]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.024(Δ/σ)max < 0.001
wR(F2) = 0.044Δρmax = 0.52 e Å3
S = 0.82Δρmin = 0.50 e Å3
3559 reflectionsAbsolute structure: refinement of Flack (1983) parameter, 1508 Friedel pairs.'
191 parametersAbsolute structure parameter: 0.03 (2)
0 restraints
Crystal data top
[Fe(C5H5)(C12H19NO)]IV = 1814.8 (8) Å3
Mr = 441.12Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 7.777 (2) ŵ = 2.53 mm1
b = 11.575 (3) ÅT = 293 K
c = 20.160 (5) Å0.5 × 0.1 × 0.1 mm
Data collection top
Rigaku AFC-5S
diffractometer
Rint = 0.051
14192 measured reflections3 standard reflections every 150 reflections
3559 independent reflections intensity decay: 2%
2211 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.024H-atom parameters constrained
wR(F2) = 0.044Δρmax = 0.52 e Å3
S = 0.82Δρmin = 0.50 e Å3
3559 reflectionsAbsolute structure: refinement of Flack (1983) parameter, 1508 Friedel pairs.'
191 parametersAbsolute structure parameter: 0.03 (2)
0 restraints
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
I0.71391 (3)0.26809 (2)0.195759 (14)0.07114 (10)
Fe0.26848 (8)0.01584 (4)0.04636 (2)0.05045 (15)
O820.1757 (4)0.1504 (2)0.30972 (15)0.0694 (8)
N70.1553 (3)0.2806 (2)0.17816 (12)0.0429 (7)
H70.04080.26720.18330.051*
C1A0.1725 (5)0.1268 (3)0.09113 (17)0.0424 (10)
C2A0.0403 (5)0.0438 (4)0.0822 (2)0.0569 (11)
H2A0.02540.01030.11560.068*
C3A0.0265 (6)0.0212 (4)0.0136 (2)0.0724 (15)
H3A0.050.03020.0060.087*
C4A0.1459 (7)0.0883 (4)0.0193 (2)0.0779 (15)
H4A0.16380.08920.06490.093*
C5A0.2355 (6)0.1546 (3)0.02713 (19)0.0649 (12)
H5A0.32170.20780.01770.078*
C1B0.4553 (11)0.0803 (7)0.1058 (4)0.129 (3)
H1B0.48810.05070.14680.154*
C2B0.3291 (9)0.1640 (6)0.0935 (4)0.109 (2)
H2B0.26010.20020.12490.131*
C3B0.3265 (7)0.1826 (4)0.0260 (3)0.0884 (16)
H3B0.25630.23560.00440.106*
C4B0.4410 (8)0.1122 (6)0.0042 (3)0.0943 (17)
H4B0.46070.10710.04960.113*
C5B0.5218 (6)0.0505 (6)0.0435 (5)0.115 (2)
H5B0.60830.00340.03610.138*
C60.2369 (5)0.1691 (3)0.15622 (16)0.0538 (10)
H620.36040.180.15330.065*
H610.21540.11050.18960.065*
C80.2227 (6)0.3275 (3)0.24370 (17)0.0501 (9)
H80.34780.31760.24530.06*
C810.1429 (4)0.2695 (4)0.3038 (2)0.0641 (10)
H8110.18490.30780.34340.077*
H8120.01940.28090.30210.077*
C830.3441 (6)0.1247 (4)0.3327 (2)0.0827 (16)
H8310.4270.15340.30150.124*
H8320.35690.04260.33710.124*
H8330.36210.16080.3750.124*
C90.1810 (7)0.4546 (3)0.2396 (2)0.0843 (15)
H920.06770.46980.25770.101*
H910.26490.49960.26420.101*
C100.1868 (7)0.4844 (3)0.1679 (2)0.0897 (15)
H1020.0920.53530.15680.108*
H1010.29360.52380.15760.108*
C110.1743 (7)0.3768 (3)0.12967 (19)0.0741 (15)
H1110.2770.36590.10310.089*
H1120.07560.37950.10030.089*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C830.091 (4)0.070 (3)0.087 (4)0.001 (3)0.002 (3)0.022 (3)
I0.03903 (11)0.07530 (18)0.0991 (2)0.00156 (14)0.00217 (17)0.02420 (17)
Fe0.0531 (4)0.0514 (3)0.0468 (3)0.0055 (3)0.0028 (3)0.0049 (2)
O820.074 (2)0.071 (2)0.0636 (19)0.0209 (15)0.0011 (19)0.0020 (18)
N70.0370 (14)0.0415 (17)0.050 (2)0.0004 (13)0.0027 (12)0.0027 (16)
C1A0.043 (3)0.046 (2)0.038 (2)0.0025 (18)0.0050 (19)0.0045 (18)
C2A0.050 (3)0.065 (3)0.055 (3)0.001 (2)0.002 (2)0.007 (2)
C3A0.069 (3)0.076 (4)0.073 (4)0.015 (3)0.023 (3)0.028 (3)
C4A0.118 (4)0.073 (3)0.044 (3)0.029 (3)0.001 (3)0.004 (3)
C5A0.084 (4)0.050 (2)0.061 (3)0.004 (2)0.016 (3)0.002 (2)
C1B0.142 (7)0.135 (7)0.109 (6)0.097 (6)0.075 (5)0.049 (5)
C2B0.141 (6)0.101 (5)0.086 (5)0.062 (4)0.034 (4)0.036 (3)
C3B0.096 (4)0.049 (3)0.120 (5)0.009 (3)0.005 (4)0.014 (3)
C4B0.095 (5)0.098 (5)0.090 (4)0.032 (4)0.026 (4)0.007 (4)
C5B0.048 (3)0.096 (5)0.200 (8)0.007 (3)0.014 (5)0.010 (6)
C60.045 (3)0.056 (2)0.060 (2)0.0053 (19)0.001 (2)0.0201 (19)
C80.046 (2)0.048 (2)0.056 (2)0.005 (2)0.004 (2)0.0147 (18)
C810.056 (2)0.079 (3)0.058 (3)0.008 (2)0.001 (2)0.014 (3)
C90.110 (4)0.051 (3)0.092 (4)0.012 (3)0.016 (3)0.024 (3)
C100.116 (4)0.047 (3)0.105 (4)0.012 (3)0.010 (3)0.002 (3)
C110.107 (5)0.055 (3)0.060 (3)0.008 (3)0.017 (3)0.009 (2)
Geometric parameters (Å, º) top
Fe—C1A2.025 (3)C2B—H2B0.93
Fe—C2A2.037 (4)C3B—C4B1.352 (6)
Fe—C3A2.040 (4)C3B—H3B0.93
Fe—C4A2.029 (4)C4B—H4B0.93
Fe—C5A2.027 (4)C5B—C1B1.402 (9)
Fe—C1B2.026 (5)C5B—C4B1.353 (8)
Fe—C2B2.017 (5)C5B—H5B0.93
Fe—C3B2.024 (4)C6—C1A1.488 (4)
Fe—C4B2.021 (5)C6—H620.97
Fe—C5B2.011 (5)C6—H610.97
O82—C811.407 (4)C8—C91.509 (4)
N7—C61.505 (4)C8—H80.98
N7—C81.522 (4)C81—C81.517 (5)
N7—C111.489 (4)C81—H8110.97
N7—H70.91C81—H8120.97
C1A—C5A1.417 (5)C83—O821.420 (5)
C2A—C1A1.418 (5)C83—H8310.96
C2A—C3A1.412 (5)C83—H8320.96
C2A—H2A0.93C83—H8330.96
C3A—C4A1.381 (6)C9—C101.487 (5)
C3A—H3A0.93C9—H920.97
C4A—C5A1.397 (6)C9—H910.97
C4A—H4A0.93C10—C111.468 (5)
C5A—H5A0.93C10—H1020.97
C1B—H1B0.93C10—H1010.97
C2B—C1B1.402 (8)C11—H1110.97
C2B—C3B1.377 (6)C11—H1120.97
C5B—Fe—C1A122.5 (3)C4A—C5A—Fe69.9 (2)
C2B—Fe—C1A124.8 (2)C1A—C5A—Fe69.4 (2)
C4B—Fe—C1A156.9 (2)C4A—C5A—H5A125.9
C3B—Fe—C1A161.9 (2)C1A—C5A—H5A125.9
C5B—Fe—C2A158.6 (3)Fe—C5A—H5A126.4
C2B—Fe—C2A109.0 (2)C5B—C1B—C2B105.6 (6)
C4B—Fe—C2A160.8 (2)C5B—C1B—Fe69.1 (3)
C3B—Fe—C2A126.1 (2)C2B—C1B—Fe69.3 (3)
C1A—Fe—C2A40.87 (14)C5B—C1B—H1B127.2
C1B—Fe—C2A122.7 (3)C2B—C1B—H1B127.2
C5A—Fe—C2A68.14 (17)Fe—C1B—H1B125.9
C4A—Fe—C2A67.74 (18)C3B—C2B—C1B107.1 (6)
C5B—Fe—C3A159.4 (3)C3B—C2B—Fe70.4 (3)
C2B—Fe—C3A123.1 (3)C1B—C2B—Fe70.1 (3)
C4B—Fe—C3A124.4 (2)C3B—C2B—H2B126.5
C3B—Fe—C3A109.9 (2)C1B—C2B—H2B126.5
C1A—Fe—C3A68.46 (16)Fe—C2B—H2B124.7
C1B—Fe—C3A158.5 (4)C4B—C3B—C2B110.0 (5)
C5A—Fe—C3A67.5 (2)C4B—C3B—Fe70.4 (3)
C4A—Fe—C3A39.69 (17)C2B—C3B—Fe69.8 (3)
C2A—Fe—C3A40.54 (14)C4B—C3B—H3B125
C5B—Fe—C4A124.1 (3)C2B—C3B—H3B125
C2B—Fe—C4A157.3 (3)Fe—C3B—H3B126.4
C4B—Fe—C4A108.1 (2)C3B—C4B—C5B107.7 (6)
C3B—Fe—C4A122.6 (2)C3B—C4B—Fe70.6 (3)
C1A—Fe—C4A68.49 (15)C5B—C4B—Fe70.0 (3)
C1B—Fe—C4A160.4 (4)C3B—C4B—H4B126.2
C5A—Fe—C4A40.31 (16)C5B—C4B—H4B126.2
C5B—Fe—C5A108.2 (2)Fe—C4B—H4B124.8
C2B—Fe—C5A161.4 (3)C4B—C5B—C1B109.7 (6)
C4B—Fe—C5A121.7 (2)C4B—C5B—Fe70.8 (3)
C3B—Fe—C5A156.6 (2)C1B—C5B—Fe70.2 (3)
C1A—Fe—C5A40.95 (13)C4B—C5B—H5B125.2
C1B—Fe—C5A124.2 (3)C1B—C5B—H5B125.2
C5B—Fe—C1B40.6 (2)Fe—C5B—H5B125.4
C2B—Fe—C1B40.6 (2)C1A—C6—N7113.5 (3)
C4B—Fe—C1B67.6 (2)C1A—C6—H62108.9
C3B—Fe—C1B67.0 (2)N7—C6—H62108.9
C1A—Fe—C1B107.5 (2)C1A—C6—H61108.9
C5B—Fe—C2B67.3 (3)N7—C6—H61108.9
C5B—Fe—C3B65.5 (2)H62—C6—H61107.7
C2B—Fe—C3B39.86 (18)C9—C8—C81112.8 (4)
C4B—Fe—C3B39.04 (19)C9—C8—N7103.1 (3)
C5B—Fe—C4B39.2 (2)C81—C8—N7113.2 (3)
C2B—Fe—C4B67.2 (2)C9—C8—H8109.2
C81—O82—C83113.6 (3)C81—C8—H8109.2
C11—N7—C8105.6 (3)N7—C8—H8109.2
C6—N7—C8114.6 (3)O82—C81—C8115.3 (3)
C11—N7—C6114.0 (3)O82—C81—H811108.5
C11—N7—H7107.4C8—C81—H811108.5
C6—N7—H7107.4O82—C81—H812108.5
C8—N7—H7107.4C8—C81—H812108.5
C5A—C1A—C2A106.8 (3)H811—C81—H812107.5
C5A—C1A—C6127.7 (4)O82—C83—H831109.5
C2A—C1A—C6125.4 (3)O82—C83—H832109.5
C5A—C1A—Fe69.6 (2)H831—C83—H832109.5
C2A—C1A—Fe70.0 (2)O82—C83—H833109.5
C6—C1A—Fe122.5 (2)H831—C83—H833109.5
C3A—C2A—C1A107.8 (4)H832—C83—H833109.5
C3A—C2A—Fe69.9 (2)C10—C9—C8105.8 (3)
C1A—C2A—Fe69.1 (2)C10—C9—H92110.6
C3A—C2A—H2A126.1C8—C9—H92110.6
C1A—C2A—H2A126.1C10—C9—H91110.6
Fe—C2A—H2A126.5C8—C9—H91110.6
C4A—C3A—C2A108.4 (4)H92—C9—H91108.7
C4A—C3A—Fe69.7 (3)C11—C10—C9108.2 (3)
C2A—C3A—Fe69.6 (2)C11—C10—H102110.1
C4A—C3A—H3A125.8C9—C10—H102110.1
C2A—C3A—H3A125.8C11—C10—H101110.1
Fe—C3A—H3A126.4C9—C10—H101110.1
C3A—C4A—C5A108.8 (4)H102—C10—H101108.4
C3A—C4A—Fe70.6 (3)C10—C11—N7107.3 (3)
C5A—C4A—Fe69.8 (2)C10—C11—H111110.3
C3A—C4A—H4A125.6N7—C11—H111110.3
C5A—C4A—H4A125.6C10—C11—H112110.3
Fe—C4A—H4A125.6N7—C11—H112110.3
C4A—C5A—C1A108.3 (4)H111—C11—H112108.5
C83—O82—C81—C876.4 (4)C2B—Fe—C2A—C1A121.6 (3)
C5B—Fe—C2B—C3B78.4 (4)C4B—Fe—C2A—C1A163.4 (6)
C4B—Fe—C2B—C3B35.7 (3)C3B—Fe—C2A—C1A162.7 (3)
C1A—Fe—C2B—C3B166.9 (3)C1B—Fe—C2A—C1A78.8 (4)
C1B—Fe—C2B—C3B117.4 (6)C5A—Fe—C2A—C1A38.7 (2)
C5A—Fe—C2B—C3B158.2 (6)C4A—Fe—C2A—C1A82.4 (3)
C4A—Fe—C2B—C3B46.7 (7)C3A—Fe—C2A—C1A119.2 (4)
C2A—Fe—C2B—C3B124.1 (4)C1A—C2A—C3A—C4A0.2 (5)
C3A—Fe—C2B—C3B81.5 (4)Fe—C2A—C3A—C4A59.1 (3)
C5B—Fe—C2B—C1B39.0 (4)C1A—C2A—C3A—Fe58.9 (3)
C4B—Fe—C2B—C1B81.7 (4)C5B—Fe—C3A—C4A44.4 (8)
C3B—Fe—C2B—C1B117.4 (6)C2B—Fe—C3A—C4A159.8 (3)
C1A—Fe—C2B—C1B75.7 (5)C4B—Fe—C3A—C4A76.3 (4)
C5A—Fe—C2B—C1B40.8 (9)C3B—Fe—C3A—C4A117.5 (3)
C4A—Fe—C2B—C1B164.1 (5)C1A—Fe—C3A—C4A81.9 (3)
C2A—Fe—C2B—C1B118.4 (5)C1B—Fe—C3A—C4A165.0 (6)
C3A—Fe—C2B—C1B161.1 (4)C5A—Fe—C3A—C4A37.5 (2)
C2B—Fe—C5B—C4B81.3 (4)C2A—Fe—C3A—C4A119.7 (4)
C3B—Fe—C5B—C4B37.6 (4)C5B—Fe—C3A—C2A164.1 (7)
C1A—Fe—C5B—C4B160.9 (3)C2B—Fe—C3A—C2A80.4 (4)
C1B—Fe—C5B—C4B120.2 (6)C4B—Fe—C3A—C2A163.9 (3)
C5A—Fe—C5B—C4B118.1 (4)C3B—Fe—C3A—C2A122.8 (3)
C4A—Fe—C5B—C4B76.3 (5)C1A—Fe—C3A—C2A37.9 (3)
C2A—Fe—C5B—C4B165.5 (5)C1B—Fe—C3A—C2A45.3 (8)
C3A—Fe—C5B—C4B43.7 (9)C5A—Fe—C3A—C2A82.2 (3)
C2B—Fe—C5B—C1B39.0 (4)C4A—Fe—C3A—C2A119.7 (4)
C4B—Fe—C5B—C1B120.2 (6)C11—N7—C6—C1A56.5 (4)
C3B—Fe—C5B—C1B82.6 (4)C8—N7—C6—C1A178.4 (3)
C1A—Fe—C5B—C1B78.8 (5)C2A—C3A—C4A—C5A0.5 (5)
C5A—Fe—C5B—C1B121.7 (5)Fe—C3A—C4A—C5A59.6 (3)
C4A—Fe—C5B—C1B163.4 (4)C2A—C3A—C4A—Fe59.1 (3)
C2A—Fe—C5B—C1B45.2 (9)C5B—Fe—C4A—C3A162.7 (4)
C3A—Fe—C5B—C1B164.0 (6)C2B—Fe—C4A—C3A48.4 (7)
C1B—C2B—C3B—C4B1.8 (6)C4B—Fe—C4A—C3A122.5 (3)
Fe—C2B—C3B—C4B59.0 (4)C3B—Fe—C4A—C3A82.1 (4)
C1B—C2B—C3B—Fe60.8 (4)C1A—Fe—C4A—C3A81.8 (3)
C5B—Fe—C3B—C4B37.8 (4)C1B—Fe—C4A—C3A163.6 (6)
C2B—Fe—C3B—C4B121.2 (5)C5A—Fe—C4A—C3A119.6 (4)
C1A—Fe—C3B—C4B158.1 (5)C2A—Fe—C4A—C3A37.6 (3)
C1B—Fe—C3B—C4B82.4 (4)C5B—Fe—C4A—C5A77.7 (4)
C5A—Fe—C3B—C4B41.4 (7)C2B—Fe—C4A—C5A168.0 (5)
C4A—Fe—C3B—C4B78.2 (4)C4B—Fe—C4A—C5A117.9 (3)
C2A—Fe—C3B—C4B163.1 (3)C3B—Fe—C4A—C5A158.4 (3)
C3A—Fe—C3B—C4B120.5 (4)C1A—Fe—C4A—C5A37.8 (2)
C5B—Fe—C3B—C2B83.4 (4)C1B—Fe—C4A—C5A44.0 (7)
C4B—Fe—C3B—C2B121.2 (5)C2A—Fe—C4A—C5A82.0 (3)
C1A—Fe—C3B—C2B36.9 (8)C3A—Fe—C4A—C5A119.6 (4)
C1B—Fe—C3B—C2B38.9 (4)C3A—C2A—C1A—C5A0.8 (4)
C5A—Fe—C3B—C2B162.6 (6)Fe—C2A—C1A—C5A60.2 (3)
C4A—Fe—C3B—C2B160.5 (4)C3A—C2A—C1A—C6175.7 (3)
C2A—Fe—C3B—C2B75.7 (4)Fe—C2A—C1A—C6116.3 (3)
C3A—Fe—C3B—C2B118.3 (4)C3A—C2A—C1A—Fe59.4 (3)
C4B—C5B—C1B—C2B0.1 (7)N7—C6—C1A—C5A88.0 (4)
Fe—C5B—C1B—C2B60.1 (4)N7—C6—C1A—C2A96.2 (4)
C4B—C5B—C1B—Fe60.0 (4)N7—C6—C1A—Fe176.3 (2)
C3B—C2B—C1B—C5B1.0 (6)C5B—Fe—C1A—C5A80.3 (4)
Fe—C2B—C1B—C5B60.0 (4)C2B—Fe—C1A—C5A163.8 (4)
C3B—C2B—C1B—Fe61.0 (4)C4B—Fe—C1A—C5A48.5 (6)
C2B—Fe—C1B—C5B116.8 (6)C3B—Fe—C1A—C5A168.3 (6)
C4B—Fe—C1B—C5B36.2 (4)C1B—Fe—C1A—C5A122.4 (4)
C3B—Fe—C1B—C5B78.6 (4)C4A—Fe—C1A—C5A37.2 (3)
C1A—Fe—C1B—C5B119.8 (5)C2A—Fe—C1A—C5A117.6 (3)
C5A—Fe—C1B—C5B77.8 (5)C3A—Fe—C1A—C5A80.0 (3)
C4A—Fe—C1B—C5B44.8 (8)C5B—Fe—C1A—C2A162.1 (4)
C2A—Fe—C1B—C5B162.1 (4)C2B—Fe—C1A—C2A78.6 (4)
C3A—Fe—C1B—C5B164.6 (5)C4B—Fe—C1A—C2A166.1 (5)
C5B—Fe—C1B—C2B116.8 (6)C3B—Fe—C1A—C2A50.7 (7)
C4B—Fe—C1B—C2B80.6 (4)C1B—Fe—C1A—C2A120.0 (4)
C3B—Fe—C1B—C2B38.2 (4)C5A—Fe—C1A—C2A117.6 (3)
C1A—Fe—C1B—C2B123.4 (4)C4A—Fe—C1A—C2A80.4 (3)
C5A—Fe—C1B—C2B165.4 (4)C3A—Fe—C1A—C2A37.6 (2)
C4A—Fe—C1B—C2B161.7 (5)C5B—Fe—C1A—C642.1 (5)
C2A—Fe—C1B—C2B81.1 (5)C2B—Fe—C1A—C641.3 (5)
C3A—Fe—C1B—C2B47.8 (8)C4B—Fe—C1A—C674.0 (6)
C2B—C3B—C4B—C5B1.8 (6)C3B—Fe—C1A—C669.2 (7)
Fe—C3B—C4B—C5B60.5 (4)C1B—Fe—C1A—C60.1 (5)
C2B—C3B—C4B—Fe58.7 (4)C5A—Fe—C1A—C6122.5 (4)
C1B—C5B—C4B—C3B1.2 (7)C4A—Fe—C1A—C6159.7 (4)
Fe—C5B—C4B—C3B60.9 (4)C2A—Fe—C1A—C6119.9 (4)
C1B—C5B—C4B—Fe59.7 (4)C3A—Fe—C1A—C6157.5 (4)
C5B—Fe—C4B—C3B118.1 (6)C81—C8—C9—C10152.3 (4)
C2B—Fe—C4B—C3B36.5 (3)N7—C8—C9—C1029.8 (5)
C1A—Fe—C4B—C3B162.8 (4)C8—C9—C10—C1118.0 (6)
C1B—Fe—C4B—C3B80.6 (4)C9—C10—C11—N71.7 (6)
C5A—Fe—C4B—C3B162.0 (3)C6—N7—C11—C10147.2 (4)
C4A—Fe—C4B—C3B119.8 (4)C8—N7—C11—C1020.6 (5)
C2A—Fe—C4B—C3B45.8 (8)C3A—C4A—C5A—C1A1.0 (5)
C3A—Fe—C4B—C3B79.1 (4)Fe—C4A—C5A—C1A59.0 (3)
C2B—Fe—C4B—C5B81.6 (4)C3A—C4A—C5A—Fe60.1 (3)
C3B—Fe—C4B—C5B118.1 (6)C2A—C1A—C5A—C4A1.1 (5)
C1A—Fe—C4B—C5B44.7 (7)C6—C1A—C5A—C4A175.3 (4)
C1B—Fe—C4B—C5B37.5 (4)Fe—C1A—C5A—C4A59.3 (3)
C5A—Fe—C4B—C5B79.9 (5)C2A—C1A—C5A—Fe60.5 (3)
C4A—Fe—C4B—C5B122.1 (5)C6—C1A—C5A—Fe115.9 (4)
C2A—Fe—C4B—C5B163.8 (6)C5B—Fe—C5A—C4A121.5 (4)
C3A—Fe—C4B—C5B162.9 (5)C2B—Fe—C5A—C4A165.5 (7)
O82—C81—C8—C9179.3 (3)C4B—Fe—C5A—C4A80.6 (4)
O82—C81—C8—N762.7 (4)C3B—Fe—C5A—C4A51.3 (6)
C11—N7—C8—C930.9 (4)C1A—Fe—C5A—C4A119.6 (4)
C6—N7—C8—C9157.2 (3)C1B—Fe—C5A—C4A163.6 (4)
C11—N7—C8—C81153.1 (3)C2A—Fe—C5A—C4A80.9 (3)
C6—N7—C8—C8180.6 (4)C3A—Fe—C5A—C4A37.0 (3)
C5B—Fe—C2A—C3A164.7 (7)C5B—Fe—C5A—C1A118.9 (4)
C2B—Fe—C2A—C3A119.2 (4)C2B—Fe—C5A—C1A45.9 (8)
C4B—Fe—C2A—C3A44.2 (7)C4B—Fe—C5A—C1A159.8 (3)
C3B—Fe—C2A—C3A78.1 (4)C3B—Fe—C5A—C1A170.9 (5)
C1A—Fe—C2A—C3A119.2 (4)C1B—Fe—C5A—C1A76.8 (4)
C1B—Fe—C2A—C3A162.0 (4)C4A—Fe—C5A—C1A119.6 (4)
C5A—Fe—C2A—C3A80.5 (3)C2A—Fe—C5A—C1A38.7 (2)
C4A—Fe—C2A—C3A36.8 (3)C3A—Fe—C5A—C1A82.6 (3)
C5B—Fe—C2A—C1A45.5 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N7—H7···Ii0.912.553.454 (5)170
C6—H62···I0.973.053.963 (6)157
C8—H8···I0.983.074.000 (7)159
C6—H61···O820.972.483.138 (7)125
C10—H102···O82ii0.972.563.441 (6)151
Symmetry codes: (i) x1, y, z; (ii) x, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula[Fe(C5H5)(C12H19NO)]I
Mr441.12
Crystal system, space groupOrthorhombic, P212121
Temperature (K)293
a, b, c (Å)7.777 (2), 11.575 (3), 20.160 (5)
V3)1814.8 (8)
Z4
Radiation typeMo Kα
µ (mm1)2.53
Crystal size (mm)0.5 × 0.1 × 0.1
Data collection
DiffractometerRigaku AFC-5S
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
14192, 3559, 2211
Rint0.051
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.024, 0.044, 0.82
No. of reflections3559
No. of parameters191
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.52, 0.50
Absolute structureRefinement of Flack (1983) parameter, 1508 Friedel pairs.'
Absolute structure parameter0.03 (2)

Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1989), MSC/AFC Diffractometer Control Software, TEXSAN (Molecular Structure Corporation, 1989), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), PARST (Nardelli, 1996).

Selected geometric parameters (Å, º) top
O82—C811.407 (4)N7—C111.489 (4)
N7—C61.505 (4)C6—C1A1.488 (4)
N7—C81.522 (4)C83—O821.420 (5)
C81—O82—C83113.6 (3)C11—N7—C6114.0 (3)
C11—N7—C8105.6 (3)C1A—C6—N7113.5 (3)
C6—N7—C8114.6 (3)C81—C8—N7113.2 (3)
C6—N7—C8—C8180.6 (4)C9—C10—C11—N71.7 (6)
C81—C8—C9—C10152.3 (4)C6—N7—C11—C10147.2 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N7—H7···Ii0.912.553.454 (5)170
C6—H62···I0.973.053.963 (6)157
C8—H8···I0.983.074.000 (7)159
C6—H61···O820.972.483.138 (7)125
C10—H102···O82ii0.972.563.441 (6)151
Symmetry codes: (i) x1, y, z; (ii) x, y+1/2, z+1/2.
 

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