Methyl 2-(4-ferrocenylbenzamido)-thiophene-3-carboxylate and ethyl 2-(4-ferrocenylbenzamido)-1,3-thiazole-4-acetate, a unique ferrocene derivative containing a thiazole moiety

Article abstract of DOI:10.1107/S010827010501783X

The conformations and hydrogen bonding in the thiophene and thiazole title compounds, [Fe(C₅H₅)(C₂₀H₁₄NO ₃S)], (I), and [Fe(C₅H₅)(C₁₉H ₁₇N₂O₃S)], (II), are discussed. The sequence (C₅H₄)-(C₆H₄)-(CONH)-(C ₄H₂S)-(CO₂Me) of rings and moieties in (I) is close to being planar; all consecutive interplanar angles are less than 10°. An intramolecular N-H...O=C_ester hydrogen bond [graph set S(6), N...O = 2.768 (2) A and N - H...O = 134 (2)°] effects the molecular planarity, and aggregation occurs via hydrogen-bonded chains formed from intermolecular C_ar - H...O=C_ester/amide interactions along [010], with C...O distances ranging from 3.401 (3) to 3.577 (2) A. The thiazole system in (II) crystallizes with two molecules in the asymmetric unit; these differ in the conformation along their long molecular axes; for example, the interplanar angle between the phenylene (C ₆H₄) and thiazole (C₃NS) rings is 8.1 (2)° in one molecule and 27.66 (14)° in the other. Intermolecular N-H...O=C_ester hydrogen bonds [N...O = 2.972 (4) and 2.971 (3) A], each augmented by a C_phenylene - H...O=C _ester interaction [3.184 (5) and 3.395 (4) A], form motifs with graph set R₂¹(7) and generate chains along [100]. The amide C=O groups do not participate in hydrogen bonding. Compound (II) is the first reported ferrocenyl-containing thiazole structure.

Full text of DOI:10.1107/S010827010501783X

metal-organic compounds
Ê
Acta Crystallographica Section C
Crystal Structure
Communications
HÁ Á ÁO Cester interaction [3.184 (5) and 3.395 (4) A], form
motifs with graph set R12(7) and generate chains along [100].
The amide C O groups do not participate in hydrogen
bonding. Compound (II) is the ®rst reported ferrocenyl-
containing thiazole structure.
ISSN 0108-2701
Comment
Methyl 2-(4-ferrocenylbenzamido)-
thiophene-3-carboxylate and ethyl
2-(4-ferrocenylbenzamido)-1,3-
Ferrocene (Fc) and its derivatives continue to attract much
attention in coordination chemistry, with important roles
encompassing both structural and electronic capabilities
thiazole-4-acetate, a unique ferrocene (Adams, 1999). Integration of ferrocene into new hybrid
systems has expanded the potential of organometallic
materials with a range of feasible applications (Togni &
derivative containing a thiazole
moiety
Halterman, 1998; Togni & Hayashi, 1995; Hudson et al., 2001).
We report here the structures of two 4-ferrocenylbenzamide
Steven Alley,a John F. Gallagher,a* Vincent M. Hooper,b
Peter T. M. Kennya* and Alan J. Loughc
systems with terminal thiophenecarboxylate, (I), and thiaz-
oleacetate groups, (II).
aSchool of Chemical Sciences, National Institute for Cellular Biotechnology, Dublin
City University, Dublin 9, Ireland, bSchool of Chemical Sciences, Dublin City
University, Dublin 9, Ireland, and cDepartment of Chemistry, 80 St George Street,
University of Toronto, Ontario, Canada M5S 3H6
Correspondence e-mail: john.gallagher@dcu.ie, peter.kenny@dcu.ie
Received 5 May 2005
Aview of (I) with the atomic numbering scheme is shown in
Fig. 1. Bond lengths and angles are in accord with anticipated
Accepted 6 June 2005
Online 30 June 2005
values (Allen, 2002). In (I), the FeÐC bond lengths for the
5
Ê
The conformations and hydrogen bonding in the thiophene
and thiazole title compounds, [Fe(C5H5)(C20H14NO3S)], (I),
and [Fe(C5H5)(C19H17N2O3S)], (II), are discussed. The
sequence (C5H4)±(C6H4)±(CONH)±(C4H2S)±(CO2Me) of
rings and moieties in (I) is close to being planar; all
consecutive interplanar angles are less than 10ꢀ. An intra-
molecular NÐHÁ Á ÁO Cester hydrogen bond [graph set S(6),
substituted ꢀ -C5H4 ring are in the range 2.038 (2)±2.054 (2) A
and are similar to those in the ꢀ5-C5H5 ring [2.037 (2)±
Ê
2.054 (2) A]; the FeÁ Á ÁCg1 and FeÁ Á ÁCg2 distances are
Ê
1.6462 (10) and 1.6525 (10) A, respectively, the Cg1Á Á Á
Fe1Á Á ÁCg2 angle is 177.20 (5)ꢀ, and the C5/C5 interplanar
angle is 3.81 (15)ꢀ [Cg1 and Cg2 are the ꢀ5-C5H4 and ꢀ5(C5H5)
ring centroids, respectively]. The ꢀ5C5 rings are slightly
staggered from eclipsed geometry, with the ®ve C1nÁ Á Á
Cg1Á Á ÁCg2Á Á ÁC2n pseudo-torsion angles in the range
12.24 (16)±12.79 (15)ꢀ (n = 1±5).
ꢀ
Ê
NÁ Á ÁO = 2.768 (2) A and NÐHÁ Á ÁO = 134 (2) ] effects
the molecular planarity, and aggregation occurs via
hydrogen-bonded chains formed from intermolecular CarÐ
HÁ Á ÁO Cester/amide interactions along [010], with CÁ Á ÁO
The related 4-FcC6H4CO2R carboxylates [R = Me (Savage
i
et al., 2002), Et and Pr (Anderson et al., 2003)] have confor-
Ê
distances ranging from 3.401 (3) to 3.577 (2) A. The thiazole
system in (II) crystallizes with two molecules in the
asymmetric unit; these differ in the conformation along their
long molecular axes; for example, the interplanar angle
between the phenylene (C6H4) and thiazole (C3NS) rings is
8.1 (2)ꢀ in one molecule and 27.66 (14)ꢀ in the other.
mations that can be de®ned by the interplanar angles between
the ꢀ5-C5H4 and C6H4 rings, and between the C6H4 ring and
carboxylate CO2R group. These are, respectively, 9.35 (13) and
8.5 (2)ꢀ for Me, 6.88 (12) and 2.59 (17)ꢀ for Et, and 10.5 (2)
i
and 19.5 (5)ꢀ for Pr. In (I), the (C5H4)±(C6H4)±(CONH)±
Intermolecular NÐHÁ Á ÁO Cester hydrogen bonds [NÁ Á ÁO =
(C4H2S)±(CO2Me) system has interplanar angles between
successive C5H4, C6H4, CONH, C4H2S and CO2Me moieties of
Ê
2.972 (4) and 2.971 (3) A], each augmented by a Cphenylene
Ð
Figure 1
A view of (I), with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
Acta Cryst. (2005). C61, m365±m369 DOI: 10.1107/S010827010501783X
# 2005 International Union of Crystallography m365

metal-organic compounds
9.36 (11), 8.79 (17), 1.97 (14) and 6.33 (11)ꢀ, respectively.
Apart from slight twisting, no ring bending occurs along the
long molecular axis as a result of steric effects; this situation is
in contrast to that found in 2-(ferrocenyl)thiophene-3-
carboxylic acid (Gallagher et al., 2001), where signi®cant
bending from linearity occurs in the thienyl ring relative to the
ꢀ5-C5H4 ring to which it is bonded.
Ê
C23B/C24B = 2.005 (4)/2.023 (5) A]. These FeÐC C atoms
2
Ê
have the largest Ueq values, cf. 0.0785 (17) and 0.0733 (15) A
2
versus an average Ueq of 0.043 A for all 48 C atoms present
Ê
(Spek, 2002); however, no disorder is present and the bond-
length contraction must be a result of a small measure of
Ê
librational motion and ring slippage (0.06 A). The FeÁ Á ÁCg1/
Ê
Cg2 distances are 1.6407 (17) and 1.6450 (18) A in A, and
Ê
Methyl 2-[(ferrocenylcarbonyl)amino]thiophene-3-carboxyl-
ate, (C5H5)Fe(C5H4)±(CONH)±(C4H2S)±(CO2Me), (III)
(Alley et al., 2005), differs from (I) in that it does not have the
1,4-phenylene C6H4 ring between the C5H4 and CONH
groups. Geometric data are comparable in the two structures,
1.6400 (17) and 1.644 (2) A in B, the Cg1Á Á ÁFe1Á Á ÁCg2 angles
are 178.76 (9) and 178.96 (10)ꢀ, and both C5/C5 interplanar
angles are 1.6 (3)ꢀ [Cg1 and Cg2 are de®ned as for (I) above].
The ꢀ5C5 rings deviate from eclipsed geometry, with ®ve
C1nÁ Á ÁCg1Á Á ÁCg2Á Á ÁC2n (n = 1±5) pseudo-torsion angles
ranging from 13.5 (3) to 14.5 (3)ꢀ in A and from 5.7 (3) to
7.3 (3)ꢀ in B, in the same sense as in A.
ꢀ
Ê
with maximum differences within 0.01 A and 2 for the
amidothiophenecarboxylate residues. The CÐSÐC and SÐ
CÐN(H) angles are 90.98 (10) and 123.58 (15)ꢀ in (I), and
90.93 (11) and 123.54 (16)ꢀ in (III); the Cambridge Structural
Database (CSD; Version 5.26 of February 2005; Allen, 2002)
average for thiophene CÐSÐC angles is 92.0ꢀ (range 88.7±
97.9ꢀ). For SÐC Ccarboxy angles, the average is 111.4ꢀ (range
105.5±113.9ꢀ); the equivalent S1ÐC2 C3 angles in (I) and
(III) are 111.89 (15) and 111.94 (15)ꢀ, respectively (Allen,
2002). CSD analysis shows that both (I) and (III) have regular
amidothiophenecarboxylate moieties.
A minor conformational difference between molecules A
and B is in the orientation of the FcÐC6H4± moiety with
respect to the CONH±(thiazolyl)±CO2Et fragment, resulting
in the O1AÐC1AÐC34AÐC33A [171.9 (3)ꢀ] and O1BÐ
C1BÐC34BÐC33B [161.3 (3)ꢀ] torsion angles being signi®-
cantly different. The amidothiazole groups adopt similar
conformations in the two molecules, with NÐH cis to N and
C O cis to S. A search of the CSD for this fragment gave 11
hits all with this same orientation, indicating that this is a
An intramolecular NÐHÁ Á ÁO Cester hydrogen bond
(Table 1) forms a ring in (I), with graph set S(6) (Bernstein et
al., 1995), thus enforcing planarity along the molecular axis;
preferred solid-state conformation. The cis-oriented pairs of
Ê
Ê
2.669 (2) and 2.660 (3) A, respectively, and are oriented in a
NÁ Á ÁN and OÁ Á ÁS distances are 2.333 (4) and 2.342 (4) A, and
Ê
the NÁ Á ÁO distance is 2.768 (2) A, slightly longer than the
suitable fashion for bidentate coordination to metal systems.
As found for (I), molecule A contains consecutive ring and
moiety planes that are essentially coplanar along the long
molecular axis; however, in molecule B, the interplanar twists
are larger; for example, the C6H4 and amide O CÐN(H)
Ê
corresponding value [2.727 (2) A] in (III). Molecules of (I)
assemble as one-dimensional chains along the b-axis direction
through CÐHÁ Á ÁO C interactions, as shown in Fig. 2 with
details in Table 1. These generate R12(7) and R32(15) motifs
that, in combination with the S(6) ring, produce a larger
R22(20) ring. Overall, the crystal structure comprises one-
dimensional chains, aggregating via weak C7Ð
H7CÁ Á Áꢁ(thienyl) contacts (H7CÁ Á ÁCg3 = 2.83 A; symmetry
code as in Table 1), which link pairs of screw-axis-related
chains to form a ladder extending along [010]; there are
normal van der Waals separations between pairs of ladders.
Examination of (I) with PLATON (Spek, 2002) reveals no
solvent-accessible voids in the crystal structure and a packing
index of 72.6.
iii
iii
Ê
Compound (II) is the ®rst structurally characterized ferro-
cene derivative containing a thiazole moiety to be reported,
and this compound crystallizes with two molecules (A and B)
in the asymmetric unit of space group P1, as shown in Figs. 3(a)
and 3(b). The conformations of these molecules differ slightly
along their long molecular axes with respect to the orienta-
tions of the amidothiazoleacetate groups, and there is some
minor ethoxy disorder [0.915 (7):0.085 (7)] in molecule A.
Bond lengths and angles are unexceptional and are compar-
able to data available from corresponding fragments available
in the CSD.
In (II), the FeÐC bond lengths for the ꢀ5-C5H4 ring in A are
Ê
in the range 2.031 (4)±2.048 (3) A and are similar to those
5
Ê
[2.033 (3)±2.040 (4) A] for the ꢀ -C5H5 ring. Molecule B has
Figure 2
A view of the hydrogen-bond interactions (dashed lines) in the crystal
structure of (I). [Symmetry codes: (*) x, 1 + y, z; (#) x, 1 + y, z.]
Ê
similar values [2.032 (4)±2.047 (3) A] for the substituted ring
but two contrasting FeÁ Á Áꢀ5-C5H5 bond lengths [i.e. Fe1Ð
ꢁ
m366 Alley et al. [Fe(C5H5)(C20H14NO3S)] and [Fe(C5H5)(C19H17NO3S)]
Acta Cryst. (2005). C61, m365±m369

metal-organic compounds
Figure 3
(a) Aview of the major conformer of molecule A in (II) and (b) a view of molecule B in (II), with the atomic numbering schemes. Displacement ellipsoids
are drawn at the 30% probability level.
group planes are inclined at an angle of 17.2 (3)ꢀ (Figs. 3a and
3b). In tandem, slight bending occurs along the long molecular
axis in molecule A, as evidenced by the C11nÐC31nÁ Á ÁC34n
angle [176.4 (2)ꢀ; n = A or B], in contrast to the near linear
value [178.46 (19)ꢀ] in B.
In (II), intermolecular NamideÐHÁ Á ÁO Cester hydrogen
bonds link the molecules, forming chains extending along
[100], as shown in Fig. 4 with details in Table 2. This inter-
action, in combination with CÐHÁ Á ÁO Cester interactions,
results in hydrogen-bonded rings with graph set R12(7),
augmented by weaker secondary contacts C7B*Á Á ÁN2A and
C7AÁ Á ÁN2B (involving thiazole N atoms). Combination with
the NÐHÁ Á ÁO C hydrogen bonds produces rings with graph
sets R22(9) and, overall for the pairs of rings, R22(12). The chains
are linked into a ladder structure extending along [100] by
hydrogen bonding. The packing index is 68.9 based on the
major conformation of molecule A.
Of interest for comparison with (II) are the high-precision
structural data for the molecular structure of thiazole (IV)
from a combined analysis of gas-phase electron diffraction
data, rotational constants and ab initio calculations (Bone et
al., 1999). The corresponding mean values for (II) are SÐ
Ê
Ê
C(C) = 1.713 (2) A, SÐC(N) = 1.730 (6) A, CÐN =
Ê
Ê
1.391 (2) A and C N = 1.299 (2) A, demonstrating that the
thiazole groups are relatively unperturbed through molecular
or crystal packing forces in (II) and are comparable to the gas-
phase structure data for (IV).
C5AÐH5AÁ Á Áꢁ(thiaz-B)# interactions [symmetry code: (#)
Ê
x, y, 1
comparable C5BÁ Á Áꢁ(thiaz-A) interaction is present; the
z; C5AÁ Á Áꢁ(thiaz-centroid) = 3.511 (4) A]. No
thiazole S atoms and amide C O groups are not involved in
A search for amidothienyl and amidothiazolyl fragments in
crystal structures in the CSD reveals seven and 21 systems
(with coordinates), respectively. A search for structures
incorporating the ferrocenyl moiety (as C5FeC5) and a thio-
phene-type heteroaromatic ring yielded 30 structures; when
the thiophene-type ring was replaced with a thiazole hetero-
aromatic ring, there were no hits. This lack of structural data is
somewhat unusual given the vast output of structural ferro-
cene research to date (Adams, 1999; Allen 2002). For
comparison, a CSD search with ferrocene and pyridinyl (as
C5N) gives a total of 335 structures, revealing the wealth of
structural data available for N-heteroaromatic groups, such as
Figure 4
The hydrogen-bonding pattern involving molecules A and B in (II).
Hydrogen bonds are shown as dashed lines. [Symmetry codes: (*) 1 x,
1
y, 1 z; ($) x, 1 y, 1 z.]
ꢁ
Acta Cryst. (2005). C61, m365±m369
Alley et al.
[Fe(C5H5)(C20H14NO3S)] and [Fe(C5H5)(C19H17NO3S)] m367

metal-organic compounds
Compound (II)
pyridine donor ligands, in ferrocene chemistry when compared
with S-heteroaromatic systems, such as thiazole (Allen, 2002).
Studies are in progress to extend the synthetic, structural and
electrochemistry of these new systems in coordination chem-
istry.
Crystal data
[Fe(C5H5)(C19H17NO3S)]
Mr = 474.36
Triclinic, P1
Z = 4
Dx = 1.476 Mg m
Mo Kꢃ radiation
3
Ê
Ê
a = 12.7466 (4) A
Cell parameters from 12087
re¯ections
b = 12.8752 (8) A
Experimental
c = 13.5661 (7) A
ꢄ = 2.6±27.5ꢀ
ꢅ = 0.83 mm
T = 150 (1) K
Ê
1
ꢃ = 91.811 (3)ꢀ
ꢂ = 106.096 (3)ꢀ
ꢉ = 92.735 (3)ꢀ
Compounds (I) and (II) were synthesized according to standard
coupling procedures using 4-ferrocenylbenzoic acid as its acid
chloride and methyl 2-aminothiophene-3-carboxylate or ethyl 2-
amino-4-thiazoleacetate in yields of ca 30 and 26%, respectively.
Recrystallization, in both cases, was undertaken from petroleum
spirits/Et2O to produce red plates, (I) (m.p. 487±489 K), and an
orange crystalline solid, (II) (421±423 K). Crystals suitable for X-ray
diffraction studies were grown by diffusion of pentane vapour into a
CH2Cl2 solution of the appropriate compound. Although the synth-
eses are uncomplicated, problems arose during the puri®cation of (I)
as it decomposes on both silica and alumina to give the starting
Needle, red
0.20 Â 0.07 Â 0.04 mm
3
Ê
V = 2134.35 (18) A
Data collection
Nonius KappaCCD diffractometer
' scan and ! scans with ꢆ offsets
Absorption correction: multi-scan
(DENZO±SMN; Otwinowski &
Minor, 1997)
9714 independent re¯ections
5617 re¯ections with I > 2ꢇ(I)
Rint = 0.069
ꢄmax = 27.5ꢀ
h = 16 ! 16
Tmin = 0.851, Tmax = 0.967
15129 measured re¯ections
k = 16 ! 16
l = 16 ! 17
1
materials plus a third compound, identi®ed by H and 13C NMR as
Re®nement
methyl 4-ferrocenylbenzoate. Isolation of modest quantities of (I)
was achieved by repeated recrystallization of column fractions,
though the eventual overall yield was poor.
Re®nement on F2
R[F2 > 2ꢇ(F2)] = 0.050
wR(F2) = 0.127
S = 1.00
9714 re¯ections
w = 1/[ꢇ2(F2o) + (0.0472P)2]
where P = (F2o + 2Fc2)/3
(Á/ꢇ)max = 0.001
3
Ê
Áꢈmax = 0.35 e A
Áꢈmin =
Extinction correction: SHELXL97
3
Ê
0.47 e A
Compound (I)
573 parameters
H-atom parameters constrained
Crystal data
Extinction coef®cient: 0.0015 (4)
3
[Fe(C5H5)(C20H14NO3S)]
Mr = 445.30
Dx = 1.569 Mg m
Mo Kꢃ radiation
Cell parameters from 6335
re¯ections
Table 2
Hydrogen-bond geometry (A, ) for (II).
Monoclinic, P21=n
ꢀ
Ê
Ê
a = 10.1428 (3) A
ꢄ = 2.6±27.5ꢀ
ꢅ = 0.94 mm
T = 150 (1) K
Ê
b = 8.0965 (2) A
1
Ê
DÐHÁ Á ÁA
DÐH
HÁ Á ÁA
DÁ Á ÁA
DÐHÁ Á ÁA
c = 23.0557 (7) A
ꢂ = 95.4912 (14)ꢀ
Ê
V = 1884.67 (9) A
Z = 4
N1AÐH1AÁ Á ÁO2Biv
N1BÐH1BÁ Á ÁO2Av
C33AÐH33AÁ Á ÁO2Biv
C33BÐH33BÁ Á ÁO2Av
C7AÐH72Á Á ÁN2Bv
C7BÐH75Á Á ÁN2Aiv
0.88
0.88
0.95
0.95
0.99
0.99
2.12
2.18
2.24
2.46
2.68
2.56
2.972 (4)
2.971 (3)
3.184 (5)
3.395 (4)
3.654 (6)
3.536 (5)
162
149
173
167
168
169
3
Plate, red
0.22 Â 0.16 Â 0.10 mm
Data collection
Nonius KappaCCD diffractometer
' scan and ! scans with ꢆ offsets
Absorption correction: multi-scan
(DENZO±SMN; Otwinowski &
Minor, 1997)
4313 independent re¯ections
3441 re¯ections with I > 2ꢇ(I)
Rint = 0.049
Symmetry codes: (iv) x; y ‡ 1; z ‡ 1; (v) x ‡ 1; y ‡ 1; z ‡ 1.
ꢄmax = 27.5ꢀ
h = 13 ! 13
Tmin = 0.820, Tmax = 0.912
6335 measured re¯ections
k = 10 ! 10
Compound (I) crystallized in the monoclinic system; space group
P21/n was assigned from the systematic absences and con®rmed by
the analysis. Compound (II) crystallized in the triclinic system; space
group P1 was assumed and con®rmed by the analysis, and the
asymmetric unit was chosen so as to show clearly the overall simi-
larity of the two independent molecules A and B. It became obvious
during the re®nement of (II) that there was some slight disorder at
the terminal O3AÐC7AÐC8A moiety and this was allowed for. In
the ®nal re®nement cycles, the bond lengths of the disordered ester
group of molecule A were restrained via soft DFIX restraints to be
the same as in the ordered molecule B; a common isotropic
l = 25 ! 29
Re®nement
Re®nement on F2
R[F2 > 2ꢇ(F2)] = 0.036
wR(F2) = 0.088
S = 1.06
4313 re¯ections
268 parameters
H atoms treated by a mixture of
independent and constrained
re®nement
w = 1/[ꢇ2(F2o) + (0.033P)2
+ 1.226P]
where P = (F2o + 2Fc2)/3
(Á/ꢇ)max = 0.001
3
Ê
Áꢈmax = 0.35 e A
Áꢈmin
3
Ê
0.63 e A
=
Extinction correction: SHELXL97
Extinction coef®cient: 0.0024 (6)
2
Ê
displacement parameter of 0.035 A was assigned to the minor-
Table 1
Hydrogen-bond geometry (A, ) for (I).
ꢀ
Ê
occupancy atoms. The ®nal re®ned occupancies for the major and
minor conformers were 0.915 (7) and 0.085 (7). In (I) and (II) [except
for atom H1 bonded to N1 in (I)], all H atoms bound to C and N
atoms were treated as riding, with Uiso(H) values of 1.5Ueq(C) for
methyl H atoms and 1.2Ueq(C,N) for the remainder (methyl CÐH =
Ê
0.98 A, methylene CÐH = 0.99 A, aromatic CÐH = 0.95 A and
Ê
amide NÐH = 0.88 A). The N1ÐH1 distance in (I) re®ned to
Cg3 is the centroid of the thiophene ring.
DÐHÁ Á ÁA
DÐH
HÁ Á ÁA
DÁ Á ÁA
DÐHÁ Á ÁA
N1ÐH1Á Á ÁO2
0.81 (2)
0.95
0.95
2.14 (2)
2.56
2.56
2.65
2.83
2.768 (2)
3.411 (3)
3.401 (3)
3.577 (2)
3.604 (2)
134 (2)
150
147
165
136
Ê
Ê
C5ÐH5Á Á ÁO2i
C15ÐH15Á Á ÁO1ii
C32ÐH32Á Á ÁO1ii
C7ÐH7CÁ Á ÁCg3iii
Ê
0.81 (2) A.
0.95
0.98
For both compounds, data collection: KappaCCD Server Software
(Nonius, 1997); cell re®nement: DENZO±SMN (Otwinowski &
Symmetry codes: (i) x; y ‡ 1; z; (ii) x; y 1; z; (iii) x ‡ 12; y
;
z
.
2
1
2
1
ꢁ
m368 Alley et al. [Fe(C5H5)(C20H14NO3S)] and [Fe(C5H5)(C19H17NO3S)]
Acta Cryst. (2005). C61, m365±m369

metal-organic compounds
Bernstein, J., Davies, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem.
Int. Ed. Engl. 34, 1555±1573.
Minor, 1997); data reduction: DENZO±SMN; structure solution:
SHELXS97 (Sheldrick, 1997); structure re®nement: SHELXL97
(Sheldrick, 1997); molecular graphics: PLATON (Spek, 2002) and
ORTEX (McArdle, 1995); publication software: SHELXL97,
NRCVAX (Gabe et al., 1989) and PREP8 (Ferguson, 1998).
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