1,1′,2,2′,3,3′,4,4′-Octa­methyl­ferro­cenium 2,5-dibromo-4-hy­droxy-3,6-dioxocyclo­hexa-1,4-dien-1-olate

Mochida, T.

doi:10.1107/S1600536811025499

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page m1012

doi:10.1107/S1600536811025499

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1,1′,2,2′,3,3′,4,4′-Octamethylferrocenium 2,5-dibromo-4-hydroxy-3,6-dioxocyclohexa-1,4-dien-1-olate

Tomoyuki Mochida ^a ^*

^aDepartment of Chemistry, Graduate School of Science, Kobe University, Rokkodai, Nada, Hyogo 657-8501, Japan
^*Correspondence e-mail: tmochida@platinum.kobe-u.ac.jp

(Received 15 June 2011; accepted 28 June 2011; online 2 July 2011)

In the title salt, octamethylferrocenium bromanilate, [Fe(C₉H₁₃)₂](C₆HBr₂O₄), the Fe atom and the bromanilate anion lie on a mirror plane. The octamethylferrocenium cation adopts an eclipsed conformation. An intramolecular O—H⋯O hydrogen bond is present in the bromanilate anion. In the crystal, the cations and anions are stacked alternately, forming a one-dimensional columnar structure along [010].

Related literature

For general background to ferrocene-based charge-transfer complexes, see: Miller et al. (1994 ); Mochida et al. (2007 ). For organometallic supramolecular compounds, see: Braga et al. (2001 ); Horikoshi et al. (2004 ). For phase transitions in octa- and decamethylferrocene complexes, see: Mochida et al. (2011 ); Mochida & Yoza (2010 ). For related structures containing bromanilic acid, see: Mochida (2010 ); Thomas et al. (2009 ); Tomura & Yamashita (2000 ); Zaman et al. (2001a ,b , 2004 ). For the structure of the octamethylferrocenium cation, see: Miller et al. (1989 ).

Experimental

Crystal data

[Fe(C₉H₁₃)₂](C₆HBr₂O₄)
M_r = 595.13
Orthorhombic, P n m a
a = 14.7106 (15) Å
b = 10.4938 (11) Å
c = 14.9461 (15) Å
V = 2307.2 (4) Å³
Z = 4
Mo Kα radiation
μ = 4.15 mm⁻¹
T = 173 K
0.38 × 0.08 × 0.08 mm

Data collection

Bruker APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.306, T_max = 0.746
14287 measured reflections
2804 independent reflections
1699 reflections with I > 2σ(I)
R_int = 0.087

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.084
S = 1.00
2804 reflections
167 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1⋯O1	1.01 (8)	1.70 (9)	2.534 (5)	137 (7)

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811025499/hy2444sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811025499/hy2444Isup2.hkl

checkCIF report

Comment top

Organometallic charge-transfer salts (Miller et al., 1994; Mochida et al., 2007) and organometallic hydrogen-bonded supramolecular compounds (Braga et al., 2001, Horikoshi et al., 2004) have attracted attention mainly from the viewpoints of physical properties and crystal engineering, respectively. This paper reports the crystal structure of the title compound, a charge-transfer salt of octamethylferrocene with bromanilic acid. Bromanilic acid acts as proton donor and electron acceptor, and is useful for building organometallic complexes (Mochida, 2010; Thomas et al., 2009; Tomura & Yamashita, 2000; Zaman et al., 2001a, 2004).

The title compound consists of octamethylferrocenium cation and bromanilate anion, which is a deprotonated form of bromanilic acid (Fig. 1). The asymmetric unit contains half of the cation and half of the anion, as the Fe atom and bromanilate anion lie on a mirror plane. The Fe—C(Cp) distances in the cation are 2.072 (3)–2.120 (3) Å (average: 2.102 Å), which is a typical value of the octamethylferrocenium cation (Miller et al., 1989). The C₅HMe₄ groups of the cation adopt an eclipsed conformation and exhibit no disorder. In the anion, the C—O bond length to the deprotonated O atom is shortened compared to that to the protonated O atom [1.234 (6) versus 1.337 (6) Å]. In the crystal, the cations and anions are alternately stacked along the b-axis to form one-dimensional columns (Fig. 2). There are no intermolecular hydrogen bonds, whereas the bromanilate anion shows an intramolecular O—H···O hydrogen bond (Table 1). The local molecular arrangement closely resembles that of a decamethylferrocene–bromanilate compound (Zaman et al., 2011b), although they are not isomorphous. In both crystals, the electronegative atoms (O or Br) of the anion appear to surround the Fe atoms of the cation, leading to the co-planar arrangement of the Fe atoms and the anion planes, as seen in Fig. 2b. In this compound, no O···Br close contacts are seen, in contrast to decamethylferrocene–bromanilate compound, and C—H···Br contacts are observed between the cation and anion (H···Br distance = 3.01 Å).

DSC measurements revealed no traces of phase transitions between 120–400 K, whereas decamethyl- and octamethylferrocene complexes often undergo phase transitions associated with order-disorder of the cyclopentadienyl rings (Mochida et al., 2011; Mochida & Yoza, 2010). An exothermic peak corresponding to decomposition was observed around 408 K.

Related literature top

For general background to ferrocene-based charge-transfer complexes, see: Miller et al. (1994); Mochida et al. (2007). For organometallic supramolecular compounds, see: Braga et al. (2001); Horikoshi et al. (2004). For phase transitions in octa- and decamethylferrocene complexes, see: Mochida et al. (2011); Mochida & Yoza (2010). For related structures containing bromanilic acid, see: Mochida (2010); Thomas et al. (2009); Tomura & Yamashita (2000); Zaman et al. (2001a,b, 2004). For the structure of the octamethylferrocenium cation, see: Miller et al. (1989).

Experimental top

Violet needle crystals of the title compound were grown by slow evaporation of solvent from a 1:1 solution of octamethylferrocene and bromanilic acid in dichloromethane at 223 K. IR (KBr, cm^-1): 2919, 1642, 1562, 1368, 1336, 1167, 1030, 957, 790, 553.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level. H atoms except for the hydroxyl group are omitted for clarity. [Symmetry code: (i) x, 1/2-y, z.]
	Fig. 2. Packing diagrams of the title compound, (a) viewed along the b-axis and (b) viewed along the a-axis. H atoms are omitted for clarity in (b).

1,1',2,2',3,3',4,4'-Octamethylferrocenium 2,5-dibromo-4-hydroxy-3,6-dioxocyclohexa-1,4-dien-1-olate top

Crystal data top

[Fe(C₉H₁₃)₂](C₆HBr₂O₄)	F(000) = 1196
M_r = 595.13	D_x = 1.713 Mg m⁻³
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 1436 reflections
a = 14.7106 (15) Å	θ = 2.7–24.0°
b = 10.4938 (11) Å	µ = 4.15 mm⁻¹
c = 14.9461 (15) Å	T = 173 K
V = 2307.2 (4) Å³	Needle, violet
Z = 4	0.38 × 0.08 × 0.08 mm

Data collection top

Bruker APEX CCD diffractometer	2804 independent reflections
Radiation source: fine-focus sealed tube	1699 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.087
ϕ and ω scans	θ_max = 27.5°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −19→18
T_min = 0.306, T_max = 0.746	k = −13→13
14287 measured reflections	l = −19→15

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.084	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.032P)²] where P = (F_o² + 2F_c²)/3
2804 reflections	(Δ/σ)_max = 0.001
167 parameters	Δρ_max = 0.56 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

[Fe(C₉H₁₃)₂](C₆HBr₂O₄)	V = 2307.2 (4) Å³
M_r = 595.13	Z = 4
Orthorhombic, Pnma	Mo Kα radiation
a = 14.7106 (15) Å	µ = 4.15 mm⁻¹
b = 10.4938 (11) Å	T = 173 K
c = 14.9461 (15) Å	0.38 × 0.08 × 0.08 mm

Data collection top

Bruker APEX CCD diffractometer	2804 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1699 reflections with I > 2σ(I)
T_min = 0.306, T_max = 0.746	R_int = 0.087
14287 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.084	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.56 e Å⁻³
2804 reflections	Δρ_min = −0.39 e Å⁻³
167 parameters

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

	x	y	z	U_iso*/U_eq
Br1	0.62817 (4)	0.2500	0.60939 (4)	0.04543 (19)
Br2	0.89861 (5)	0.2500	0.25105 (4)	0.0542 (2)
Fe1	0.24413 (4)	0.2500	0.60312 (4)	0.02121 (17)
C2	0.2127 (2)	0.0859 (3)	0.5266 (2)	0.0264 (8)
C1	0.1616 (2)	0.0870 (3)	0.6081 (2)	0.0266 (8)
C5	0.2252 (2)	0.0881 (3)	0.6802 (2)	0.0298 (8)
H5	0.2094	0.0869	0.7453	0.036*
C3	0.3072 (2)	0.0853 (3)	0.5494 (2)	0.0256 (8)
C4	0.3147 (2)	0.0867 (3)	0.6443 (2)	0.0285 (8)
C8	0.3846 (2)	0.0811 (4)	0.4848 (2)	0.0410 (10)
H8A	0.4334	0.1372	0.5058	0.062*
H8B	0.3637	0.1097	0.4259	0.062*
H8C	0.4074	−0.0064	0.4803	0.062*
C7	0.1734 (3)	0.0829 (3)	0.4341 (2)	0.0389 (10)
H7A	0.1633	−0.0057	0.4160	0.058*
H7B	0.2157	0.1236	0.3923	0.058*
H7C	0.1154	0.1288	0.4335	0.058*
C9	0.4003 (2)	0.0809 (4)	0.6978 (3)	0.0420 (10)
H9A	0.4187	−0.0083	0.7052	0.063*
H9B	0.3899	0.1192	0.7567	0.063*
H9C	0.4484	0.1278	0.6666	0.063*
C6	0.0605 (2)	0.0820 (3)	0.6176 (2)	0.0415 (10)
H6A	0.0323	0.1336	0.5705	0.062*
H6B	0.0430	0.1155	0.6763	0.062*
H6C	0.0399	−0.0065	0.6121	0.062*
C12	0.7307 (4)	0.2500	0.3449 (3)	0.0328 (13)
C10	0.7062 (4)	0.2500	0.5083 (3)	0.0324 (13)
C11	0.6678 (4)	0.2500	0.4242 (3)	0.0357 (13)
C15	0.8004 (4)	0.2500	0.5240 (4)	0.0332 (13)
C14	0.8635 (4)	0.2500	0.4391 (4)	0.0365 (13)
C13	0.8211 (4)	0.2500	0.3525 (3)	0.0366 (13)
O1	0.5845 (3)	0.2500	0.4037 (2)	0.0482 (10)
O4	0.8385 (3)	0.2500	0.5975 (2)	0.0473 (11)
O3	0.9454 (3)	0.2500	0.4508 (3)	0.0532 (11)
O2	0.6862 (3)	0.2500	0.2669 (2)	0.0457 (11)
H1	0.625 (5)	0.2500	0.297 (6)	0.13 (3)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0608 (5)	0.0432 (4)	0.0323 (3)	0.000	0.0033 (3)	0.000
Br2	0.0666 (5)	0.0589 (4)	0.0373 (4)	0.000	0.0083 (3)	0.000
Fe1	0.0223 (4)	0.0178 (3)	0.0235 (4)	0.000	−0.0008 (3)	0.000
C2	0.032 (2)	0.0177 (17)	0.030 (2)	−0.0013 (16)	−0.0022 (16)	−0.0020 (15)
C1	0.0208 (18)	0.0214 (18)	0.038 (2)	−0.0037 (14)	0.0036 (16)	0.0001 (17)
C5	0.040 (2)	0.0222 (19)	0.027 (2)	−0.0008 (16)	0.0022 (17)	0.0046 (15)
C3	0.027 (2)	0.0155 (17)	0.034 (2)	0.0029 (15)	0.0043 (15)	−0.0034 (16)
C4	0.031 (2)	0.0206 (19)	0.034 (2)	0.0040 (16)	−0.0047 (16)	−0.0004 (16)
C8	0.038 (3)	0.035 (2)	0.050 (3)	0.0073 (18)	0.0156 (19)	−0.003 (2)
C7	0.055 (3)	0.029 (2)	0.032 (2)	−0.0029 (19)	−0.0125 (18)	−0.0037 (18)
C9	0.040 (2)	0.035 (2)	0.051 (3)	−0.0002 (19)	−0.0165 (19)	0.005 (2)
C6	0.028 (2)	0.036 (2)	0.060 (3)	−0.0081 (18)	0.0086 (19)	0.003 (2)
C12	0.049 (4)	0.026 (3)	0.024 (3)	0.000	−0.010 (3)	0.000
C10	0.049 (4)	0.028 (3)	0.020 (3)	0.000	−0.001 (2)	0.000
C11	0.050 (4)	0.027 (3)	0.030 (3)	0.000	−0.006 (3)	0.000
C15	0.055 (4)	0.014 (3)	0.031 (3)	0.000	−0.006 (3)	0.000
C14	0.041 (4)	0.029 (3)	0.040 (3)	0.000	−0.004 (3)	0.000
C13	0.051 (4)	0.027 (3)	0.032 (3)	0.000	0.001 (3)	0.000
O1	0.046 (3)	0.055 (3)	0.043 (2)	0.000	−0.011 (2)	0.000
O4	0.064 (3)	0.045 (3)	0.033 (2)	0.000	−0.016 (2)	0.000
O3	0.048 (3)	0.060 (3)	0.051 (3)	0.000	−0.006 (2)	0.000
O2	0.060 (3)	0.053 (3)	0.024 (2)	0.000	−0.014 (2)	0.000

Geometric parameters (Å, º) top

Br1—C10	1.898 (5)	C8—H8B	0.9800
Br2—C13	1.897 (5)	C8—H8C	0.9800
Fe1—C5ⁱ	2.072 (3)	C7—H7A	0.9800
Fe1—C5	2.072 (3)	C7—H7B	0.9800
Fe1—C4ⁱ	2.096 (3)	C7—H7C	0.9800
Fe1—C4	2.096 (3)	C9—H9A	0.9800
Fe1—C1ⁱ	2.099 (3)	C9—H9B	0.9800
Fe1—C1	2.099 (3)	C9—H9C	0.9800
Fe1—C2ⁱ	2.119 (3)	C6—H6A	0.9800
Fe1—C2	2.119 (3)	C6—H6B	0.9800
Fe1—C3ⁱ	2.120 (3)	C6—H6C	0.9800
Fe1—C3	2.120 (3)	C12—C13	1.334 (7)
C2—C1	1.432 (4)	C12—O2	1.337 (6)
C2—C3	1.433 (5)	C12—C11	1.505 (7)
C2—C7	1.499 (4)	C10—C11	1.378 (7)
C1—C5	1.427 (5)	C10—C15	1.405 (7)
C1—C6	1.495 (4)	C11—O1	1.262 (6)
C5—C4	1.422 (5)	C15—O4	1.234 (6)
C5—H5	1.0000	C15—C14	1.571 (7)
C3—C4	1.421 (5)	C14—O3	1.218 (6)
C3—C8	1.493 (4)	C14—C13	1.437 (7)
C4—C9	1.493 (4)	O2—H1	1.01 (8)
C8—H8A	0.9800

C5ⁱ—Fe1—C5	110.2 (2)	C1—C5—Fe1	71.03 (19)
C5ⁱ—Fe1—C4ⁱ	39.90 (13)	C4—C5—H5	125.6
C5—Fe1—C4ⁱ	125.03 (14)	C1—C5—H5	125.6
C5ⁱ—Fe1—C4	125.03 (14)	Fe1—C5—H5	125.6
C5—Fe1—C4	39.90 (13)	C4—C3—C2	108.2 (3)
C4ⁱ—Fe1—C4	109.68 (19)	C4—C3—C8	125.9 (3)
C5ⁱ—Fe1—C1ⁱ	40.01 (13)	C2—C3—C8	125.9 (3)
C5—Fe1—C1ⁱ	124.82 (13)	C4—C3—Fe1	69.39 (19)
C4ⁱ—Fe1—C1ⁱ	67.03 (14)	C2—C3—Fe1	70.21 (18)
C4—Fe1—C1ⁱ	160.47 (14)	C8—C3—Fe1	127.1 (2)
C5ⁱ—Fe1—C1	124.82 (13)	C3—C4—C5	107.8 (3)
C5—Fe1—C1	40.00 (13)	C3—C4—C9	126.8 (3)
C4ⁱ—Fe1—C1	160.47 (14)	C5—C4—C9	125.4 (3)
C4—Fe1—C1	67.03 (14)	C3—C4—Fe1	71.20 (19)
C1ⁱ—Fe1—C1	109.18 (18)	C5—C4—Fe1	69.14 (19)
C5ⁱ—Fe1—C2ⁱ	66.68 (13)	C9—C4—Fe1	127.5 (2)
C5—Fe1—C2ⁱ	159.65 (14)	C3—C8—H8A	109.5
C4ⁱ—Fe1—C2ⁱ	66.55 (13)	C3—C8—H8B	109.5
C4—Fe1—C2ⁱ	158.63 (14)	H8A—C8—H8B	109.5
C1ⁱ—Fe1—C2ⁱ	39.67 (12)	C3—C8—H8C	109.5
C1—Fe1—C2ⁱ	123.73 (13)	H8A—C8—H8C	109.5
C5ⁱ—Fe1—C2	159.65 (14)	H8B—C8—H8C	109.5
C5—Fe1—C2	66.68 (13)	C2—C7—H7A	109.5
C4ⁱ—Fe1—C2	158.63 (14)	C2—C7—H7B	109.5
C4—Fe1—C2	66.55 (13)	H7A—C7—H7B	109.5
C1ⁱ—Fe1—C2	123.73 (13)	C2—C7—H7C	109.5
C1—Fe1—C2	39.68 (12)	H7A—C7—H7C	109.5
C2ⁱ—Fe1—C2	108.75 (18)	H7B—C7—H7C	109.5
C5ⁱ—Fe1—C3ⁱ	66.45 (14)	C4—C9—H9A	109.5
C5—Fe1—C3ⁱ	159.74 (13)	C4—C9—H9B	109.5
C4ⁱ—Fe1—C3ⁱ	39.41 (13)	H9A—C9—H9B	109.5
C4—Fe1—C3ⁱ	124.10 (13)	C4—C9—H9C	109.5
C1ⁱ—Fe1—C3ⁱ	66.56 (13)	H9A—C9—H9C	109.5
C1—Fe1—C3ⁱ	158.65 (14)	H9B—C9—H9C	109.5
C2ⁱ—Fe1—C3ⁱ	39.52 (12)	C1—C6—H6A	109.5
C2—Fe1—C3ⁱ	123.65 (14)	C1—C6—H6B	109.5
C5ⁱ—Fe1—C3	159.74 (13)	H6A—C6—H6B	109.5
C5—Fe1—C3	66.45 (14)	C1—C6—H6C	109.5
C4ⁱ—Fe1—C3	124.10 (13)	H6A—C6—H6C	109.5
C4—Fe1—C3	39.41 (13)	H6B—C6—H6C	109.5
C1ⁱ—Fe1—C3	158.65 (14)	C13—C12—O2	124.2 (5)
C1—Fe1—C3	66.56 (13)	C13—C12—C11	123.1 (5)
C2ⁱ—Fe1—C3	123.66 (14)	O2—C12—C11	112.7 (5)
C2—Fe1—C3	39.52 (12)	C11—C10—C15	123.9 (5)
C3ⁱ—Fe1—C3	109.26 (18)	C11—C10—Br1	118.5 (4)
C1—C2—C3	107.8 (3)	C15—C10—Br1	117.6 (4)
C1—C2—C7	125.7 (3)	O1—C11—C10	128.3 (5)
C3—C2—C7	126.5 (3)	O1—C11—C12	114.0 (5)
C1—C2—Fe1	69.42 (18)	C10—C11—C12	117.8 (5)
C3—C2—Fe1	70.27 (18)	O4—C15—C10	126.6 (5)
C7—C2—Fe1	126.8 (2)	O4—C15—C14	116.8 (5)
C5—C1—C2	107.4 (3)	C10—C15—C14	116.6 (4)
C5—C1—C6	125.5 (3)	O3—C14—C13	123.9 (5)
C2—C1—C6	127.0 (3)	O3—C14—C15	118.0 (5)
C5—C1—Fe1	68.97 (18)	C13—C14—C15	118.1 (5)
C2—C1—Fe1	70.90 (18)	C12—C13—C14	120.6 (5)
C6—C1—Fe1	127.4 (2)	C12—C13—Br2	122.1 (4)
C4—C5—C1	108.8 (3)	C14—C13—Br2	117.4 (4)
C4—C5—Fe1	70.95 (19)	C12—O2—H1	92 (5)

Symmetry code: (i) x, −y+1/2, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1···O1	1.01 (8)	1.70 (9)	2.534 (5)	137 (7)

Experimental details

Crystal data
Chemical formula	[Fe(C₉H₁₃)₂](C₆HBr₂O₄)
M_r	595.13
Crystal system, space group	Orthorhombic, Pnma
Temperature (K)	173
a, b, c (Å)	14.7106 (15), 10.4938 (11), 14.9461 (15)
V (Å³)	2307.2 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	4.15
Crystal size (mm)	0.38 × 0.08 × 0.08

Data collection
Diffractometer	Bruker APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.306, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	14287, 2804, 1699
R_int	0.087
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.084, 1.00
No. of reflections	2804
No. of parameters	167
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.56, −0.39

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1···O1	1.01 (8)	1.70 (9)	2.534 (5)	137 (7)

Acknowledgements

The author thanks Y. Funasako and H. Azumi for their help with crystallography and crystal growth. This work was supported financially by KAKENHI (No. 23110719).

References

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Volume 67| Part 8| August 2011| Page m1012

doi:10.1107/S1600536811025499

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

1,1′,2,2′,3,3′,4,4′-Octa­methyl­ferro­cenium 2,5-di­bromo-4-hy­dr­oxy-3,6-dioxo­cyclo­hexa-1,4-dien-1-olate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

1,1′,2,2′,3,3′,4,4′-Octamethylferrocenium 2,5-dibromo-4-hydroxy-3,6-dioxocyclohexa-1,4-dien-1-olate