Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807016510/hb2360sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807016510/hb2360Isup2.hkl |
CCDC reference: 646608
Key indicators
- Single-crystal X-ray study
- T = 85 K
- Mean (C-C) = 0.004 Å
- R factor = 0.050
- wR factor = 0.120
- Data-to-parameter ratio = 33.0
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT480_ALERT_4_C Long H...A H-Bond Reported H17 .. BR1 .. 3.01 Ang.
Alert level G REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values From the CIF: _diffrn_reflns_theta_max 34.65 From the CIF: _reflns_number_total 7152 From the CIF: _diffrn_reflns_limit_ max hkl 8. 14. 53. From the CIF: _diffrn_reflns_limit_ min hkl -8. -15. -52. TEST1: Expected hkl limits for theta max Calculated maximum hkl 8. 15. 55. Calculated minimum hkl -8. -15. -55.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The title compound was prepared using the method of Saji et al. (1991). Yellow rectangular plates were grown by slow evaporation from a CH2Cl2–toluene (1:1 v/v) solvent system.
All H atoms were positioned geometrically, with C—H = 0.95–0.99 Å, and refined as riding, with Uiso(H) = 1.2Ueq(C).
The title compound, (I), is a useful precursor for the preparation of amino ferrocenyl derivatives (McAdam et al., 2000) or redox active surfactant systems (Saji et al., 2000) and its structure is reported here (Fig. 1). The cyclopentadienyl rings of the ferrocene are approximately eclipsed, with a mean Cm—Cg1—Cg2—Cn torsion angle of 4.2 (2)° (Cg1 and Cg2 are the centroids of the cyclopentadienyl rings, m = 12–16 and n = 17–21). The dihedral angle between the Cp ring mean planes is 4.68 (15)°. The ten-membered methylene chain of the undecanone substituent is nicely ordered and is bowed significantly towards the Fe atom. While the C11 atom lies 0.070 (3) Å above the C12···C16 ring plane, atom C1 is 0.735 (5) Å below that plane in the direction of the Fe1 atom.
In the crystal structure molecules of (I) link in a head-to-tail fashion through C17—H17···Br1 and C1···H1B···O11 hydrogen bonds to form inversion related dimers (Fig 2, Table 1). Then, C14—H14···Cg2 interactions link the dimers into an extended zigzag chain along the c axis (Fig. 3).
The title compound was prepared using the method of Saji et al. (1991). The longest methylene chain to have been examined crystallographically (Cambridge Structural Database, Version 5.28, 2007; Allen, 2002) for a similar ferrocenyl compound is 6-bromohexanoylferrocene (Hursthouse et al., 2003), while that in an organic compound is for 1-(4-tert-butylphenyl)-4-chlorobutan-1-one (Anilkumar et al., 2005). A 1,6-diferrocenylhexane-1,6-dione has also been reported (Pugh et al., 2004).
For related literature, see: McAdam et al. (2000).
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997) and TITAN2000 (Hunter & Simpson, 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997) and TITAN2000; molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97, enCIFer (Allen et al., 2004), PLATON (Spek, 2003) and PARST (Nardelli, 1995).
[Fe(C5H5)(C15H24BrO)] | F(000) = 896 |
Mr = 433.20 | Dx = 1.486 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 6638 reflections |
a = 5.6027 (2) Å | θ = 2.4–32.0° |
b = 9.8858 (4) Å | µ = 2.85 mm−1 |
c = 35.0048 (15) Å | T = 85 K |
β = 92.576 (2)° | Rectangular plate, yellow |
V = 1936.86 (13) Å3 | 0.53 × 0.12 × 0.03 mm |
Z = 4 |
Bruker APEXII CCD area-detector diffractometer | 7152 independent reflections |
Radiation source: fine-focus sealed tube | 5902 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.041 |
φ and ω scans | θmax = 34.7°, θmin = 1.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −8→8 |
Tmin = 0.700, Tmax = 0.918 | k = −15→14 |
37380 measured reflections | l = −52→53 |
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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.120 | H-atom parameters constrained |
S = 1.22 | w = 1/[σ2(Fo2) + (0.0441P)2 + 2.8882P] where P = (Fo2 + 2Fc2)/3 |
7152 reflections | (Δ/σ)max = 0.001 |
217 parameters | Δρmax = 0.97 e Å−3 |
0 restraints | Δρmin = −2.43 e Å−3 |
[Fe(C5H5)(C15H24BrO)] | V = 1936.86 (13) Å3 |
Mr = 433.20 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 5.6027 (2) Å | µ = 2.85 mm−1 |
b = 9.8858 (4) Å | T = 85 K |
c = 35.0048 (15) Å | 0.53 × 0.12 × 0.03 mm |
β = 92.576 (2)° |
Bruker APEXII CCD area-detector diffractometer | 7152 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | 5902 reflections with I > 2σ(I) |
Tmin = 0.700, Tmax = 0.918 | Rint = 0.041 |
37380 measured reflections |
R[F2 > 2σ(F2)] = 0.050 | 0 restraints |
wR(F2) = 0.120 | H-atom parameters constrained |
S = 1.22 | Δρmax = 0.97 e Å−3 |
7152 reflections | Δρmin = −2.43 e Å−3 |
217 parameters |
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. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
Br1 | 0.44415 (5) | 0.29956 (3) | 0.174591 (8) | 0.02083 (8) | |
C1 | 0.6436 (5) | 0.2608 (3) | 0.13114 (7) | 0.0179 (5) | |
H1A | 0.8027 | 0.2291 | 0.1408 | 0.022* | |
H1B | 0.5691 | 0.1874 | 0.1155 | 0.022* | |
C2 | 0.6732 (5) | 0.3844 (2) | 0.10645 (7) | 0.0168 (5) | |
H2A | 0.7894 | 0.3630 | 0.0868 | 0.020* | |
H2B | 0.7425 | 0.4579 | 0.1226 | 0.020* | |
C3 | 0.4447 (5) | 0.4366 (3) | 0.08631 (8) | 0.0186 (5) | |
H3A | 0.3292 | 0.4610 | 0.1058 | 0.022* | |
H3B | 0.3729 | 0.3633 | 0.0703 | 0.022* | |
C4 | 0.4869 (5) | 0.5596 (3) | 0.06113 (8) | 0.0198 (5) | |
H4A | 0.5480 | 0.6347 | 0.0775 | 0.024* | |
H4B | 0.6119 | 0.5370 | 0.0431 | 0.024* | |
C5 | 0.2652 (5) | 0.6077 (3) | 0.03841 (8) | 0.0191 (5) | |
H5A | 0.1404 | 0.6312 | 0.0564 | 0.023* | |
H5B | 0.2033 | 0.5326 | 0.0221 | 0.023* | |
C6 | 0.3113 (5) | 0.7300 (3) | 0.01325 (8) | 0.0184 (5) | |
H6A | 0.3603 | 0.8072 | 0.0298 | 0.022* | |
H6B | 0.4458 | 0.7090 | −0.0032 | 0.022* | |
C7 | 0.0957 (5) | 0.7721 (3) | −0.01212 (7) | 0.0177 (5) | |
H7A | −0.0379 | 0.7950 | 0.0043 | 0.021* | |
H7B | 0.0446 | 0.6945 | −0.0284 | 0.021* | |
C8 | 0.1459 (5) | 0.8929 (3) | −0.03771 (7) | 0.0159 (4) | |
H8A | 0.2858 | 0.8718 | −0.0530 | 0.019* | |
H8B | 0.1879 | 0.9719 | −0.0214 | 0.019* | |
C9 | −0.0648 (5) | 0.9311 (3) | −0.06499 (7) | 0.0167 (5) | |
H9A | −0.1051 | 0.8533 | −0.0819 | 0.020* | |
H9B | −0.2060 | 0.9513 | −0.0500 | 0.020* | |
C10 | −0.0073 (4) | 1.0539 (2) | −0.08942 (7) | 0.0146 (4) | |
H10A | 0.0461 | 1.1287 | −0.0723 | 0.017* | |
H10B | 0.1274 | 1.0306 | −0.1056 | 0.017* | |
C11 | −0.2143 (4) | 1.1037 (2) | −0.11510 (7) | 0.0126 (4) | |
O11 | −0.4154 (3) | 1.0556 (2) | −0.11395 (6) | 0.0190 (4) | |
C12 | −0.1618 (4) | 1.2151 (2) | −0.14154 (7) | 0.0112 (4) | |
C13 | −0.3250 (4) | 1.2695 (2) | −0.17037 (7) | 0.0129 (4) | |
H13 | −0.4880 | 1.2448 | −0.1745 | 0.015* | |
C14 | −0.1994 (5) | 1.3668 (2) | −0.19158 (7) | 0.0151 (4) | |
H14 | −0.2645 | 1.4185 | −0.2124 | 0.018* | |
C15 | 0.0394 (5) | 1.3739 (2) | −0.17642 (7) | 0.0143 (4) | |
H15 | 0.1610 | 1.4313 | −0.1853 | 0.017* | |
C16 | 0.0661 (4) | 1.2797 (2) | −0.14536 (7) | 0.0131 (4) | |
H16 | 0.2078 | 1.2631 | −0.1301 | 0.016* | |
Fe1 | −0.03768 (6) | 1.18054 (3) | −0.194497 (9) | 0.00942 (8) | |
C17 | −0.0130 (4) | 0.9752 (2) | −0.20303 (8) | 0.0157 (4) | |
H17 | −0.0588 | 0.9063 | −0.1859 | 0.019* | |
C18 | −0.1625 (4) | 1.0354 (3) | −0.23260 (7) | 0.0159 (4) | |
H18 | −0.3248 | 1.0132 | −0.2386 | 0.019* | |
C19 | −0.0246 (4) | 1.1347 (3) | −0.25143 (7) | 0.0154 (4) | |
H19 | −0.0794 | 1.1904 | −0.2721 | 0.018* | |
C20 | 0.2096 (4) | 1.1356 (3) | −0.23371 (7) | 0.0146 (4) | |
H20 | 0.3382 | 1.1919 | −0.2406 | 0.018* | |
C21 | 0.2170 (4) | 1.0369 (2) | −0.20378 (7) | 0.0148 (4) | |
H21 | 0.3514 | 1.0160 | −0.1873 | 0.018* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.02858 (15) | 0.01801 (13) | 0.01621 (13) | 0.00177 (10) | 0.00468 (10) | 0.00173 (9) |
C1 | 0.0245 (12) | 0.0152 (11) | 0.0143 (11) | 0.0046 (9) | 0.0026 (9) | 0.0018 (9) |
C2 | 0.0224 (12) | 0.0128 (10) | 0.0153 (11) | 0.0012 (9) | 0.0002 (9) | 0.0025 (8) |
C3 | 0.0226 (12) | 0.0162 (11) | 0.0166 (12) | −0.0005 (9) | −0.0028 (9) | 0.0043 (9) |
C4 | 0.0249 (13) | 0.0178 (11) | 0.0163 (12) | 0.0011 (10) | −0.0037 (10) | 0.0047 (9) |
C5 | 0.0236 (12) | 0.0161 (11) | 0.0172 (12) | −0.0001 (9) | −0.0022 (10) | 0.0044 (9) |
C6 | 0.0248 (13) | 0.0139 (11) | 0.0163 (12) | 0.0016 (9) | −0.0022 (10) | 0.0035 (9) |
C7 | 0.0234 (12) | 0.0158 (11) | 0.0140 (11) | 0.0022 (9) | 0.0005 (9) | 0.0046 (9) |
C8 | 0.0192 (11) | 0.0149 (10) | 0.0134 (11) | 0.0027 (8) | −0.0010 (9) | 0.0027 (8) |
C9 | 0.0202 (11) | 0.0148 (10) | 0.0155 (11) | −0.0002 (9) | 0.0034 (9) | 0.0044 (9) |
C10 | 0.0160 (10) | 0.0153 (10) | 0.0124 (10) | −0.0008 (8) | 0.0007 (8) | 0.0028 (8) |
C11 | 0.0149 (10) | 0.0125 (10) | 0.0106 (10) | 0.0014 (8) | 0.0028 (8) | 0.0004 (8) |
O11 | 0.0142 (8) | 0.0210 (9) | 0.0218 (9) | −0.0029 (7) | 0.0019 (7) | 0.0068 (7) |
C12 | 0.0134 (9) | 0.0099 (9) | 0.0103 (10) | 0.0005 (7) | 0.0013 (8) | −0.0002 (7) |
C13 | 0.0137 (10) | 0.0116 (10) | 0.0133 (10) | 0.0033 (8) | 0.0008 (8) | −0.0001 (8) |
C14 | 0.0216 (12) | 0.0098 (9) | 0.0138 (11) | 0.0039 (8) | 0.0006 (9) | 0.0013 (8) |
C15 | 0.0202 (11) | 0.0104 (9) | 0.0126 (10) | −0.0026 (8) | 0.0031 (9) | −0.0013 (8) |
C16 | 0.0169 (10) | 0.0113 (9) | 0.0108 (10) | −0.0019 (8) | −0.0003 (8) | −0.0011 (8) |
Fe1 | 0.01107 (14) | 0.00823 (14) | 0.00895 (15) | 0.00050 (11) | 0.00024 (11) | −0.00029 (11) |
C17 | 0.0162 (11) | 0.0104 (10) | 0.0207 (12) | 0.0016 (8) | 0.0010 (9) | −0.0034 (9) |
C18 | 0.0130 (10) | 0.0162 (11) | 0.0184 (11) | −0.0012 (8) | 0.0009 (8) | −0.0072 (9) |
C19 | 0.0171 (11) | 0.0186 (11) | 0.0105 (10) | 0.0029 (9) | 0.0004 (8) | −0.0022 (8) |
C20 | 0.0149 (10) | 0.0155 (10) | 0.0137 (11) | 0.0013 (8) | 0.0037 (8) | −0.0019 (8) |
C21 | 0.0145 (10) | 0.0133 (10) | 0.0168 (11) | 0.0032 (8) | 0.0022 (8) | −0.0012 (8) |
Br1—C1 | 1.965 (3) | C11—O11 | 1.225 (3) |
C1—C2 | 1.511 (3) | C11—C12 | 1.477 (3) |
C1—H1A | 0.9900 | C12—C13 | 1.436 (3) |
C1—H1B | 0.9900 | C12—C16 | 1.439 (3) |
C2—C3 | 1.523 (4) | C12—Fe1 | 2.038 (2) |
C2—H2A | 0.9900 | C13—C14 | 1.421 (3) |
C2—H2B | 0.9900 | C13—Fe1 | 2.050 (2) |
C3—C4 | 1.526 (4) | C13—H13 | 0.9500 |
C3—H3A | 0.9900 | C14—C15 | 1.419 (4) |
C3—H3B | 0.9900 | C14—Fe1 | 2.057 (2) |
C4—C5 | 1.521 (4) | C14—H14 | 0.9500 |
C4—H4A | 0.9900 | C15—C16 | 1.434 (3) |
C4—H4B | 0.9900 | C15—Fe1 | 2.053 (2) |
C5—C6 | 1.525 (4) | C15—H15 | 0.9500 |
C5—H5A | 0.9900 | C16—Fe1 | 2.042 (2) |
C5—H5B | 0.9900 | C16—H16 | 0.9500 |
C6—C7 | 1.525 (4) | Fe1—C20 | 2.042 (2) |
C6—H6A | 0.9900 | Fe1—C19 | 2.048 (2) |
C6—H6B | 0.9900 | Fe1—C21 | 2.050 (2) |
C7—C8 | 1.527 (3) | Fe1—C17 | 2.057 (2) |
C7—H7A | 0.9900 | Fe1—C18 | 2.060 (2) |
C7—H7B | 0.9900 | C17—C21 | 1.427 (3) |
C8—C9 | 1.532 (4) | C17—C18 | 1.432 (4) |
C8—H8A | 0.9900 | C17—H17 | 0.9500 |
C8—H8B | 0.9900 | C18—C19 | 1.428 (4) |
C9—C10 | 1.528 (3) | C18—H18 | 0.9500 |
C9—H9A | 0.9900 | C19—C20 | 1.426 (4) |
C9—H9B | 0.9900 | C19—H19 | 0.9500 |
C10—C11 | 1.517 (3) | C20—C21 | 1.431 (3) |
C10—H10A | 0.9900 | C20—H20 | 0.9500 |
C10—H10B | 0.9900 | C21—H21 | 0.9500 |
C2—C1—Br1 | 111.46 (17) | C14—C15—H15 | 125.8 |
C2—C1—H1A | 109.3 | C16—C15—H15 | 125.8 |
Br1—C1—H1A | 109.3 | Fe1—C15—H15 | 126.8 |
C2—C1—H1B | 109.3 | C15—C16—C12 | 107.2 (2) |
Br1—C1—H1B | 109.3 | C15—C16—Fe1 | 69.94 (14) |
H1A—C1—H1B | 108.0 | C12—C16—Fe1 | 69.19 (13) |
C1—C2—C3 | 115.3 (2) | C15—C16—H16 | 126.4 |
C1—C2—H2A | 108.5 | C12—C16—H16 | 126.4 |
C3—C2—H2A | 108.5 | Fe1—C16—H16 | 126.0 |
C1—C2—H2B | 108.5 | C12—Fe1—C16 | 41.32 (9) |
C3—C2—H2B | 108.5 | C12—Fe1—C20 | 156.54 (10) |
H2A—C2—H2B | 107.5 | C16—Fe1—C20 | 119.64 (10) |
C2—C3—C4 | 112.9 (2) | C12—Fe1—C19 | 161.95 (10) |
C2—C3—H3A | 109.0 | C16—Fe1—C19 | 154.77 (10) |
C4—C3—H3A | 109.0 | C20—Fe1—C19 | 40.80 (10) |
C2—C3—H3B | 109.0 | C12—Fe1—C13 | 41.13 (9) |
C4—C3—H3B | 109.0 | C16—Fe1—C13 | 69.27 (10) |
H3A—C3—H3B | 107.8 | C20—Fe1—C13 | 159.94 (10) |
C5—C4—C3 | 114.0 (2) | C19—Fe1—C13 | 123.98 (10) |
C5—C4—H4A | 108.7 | C12—Fe1—C21 | 121.93 (10) |
C3—C4—H4A | 108.7 | C16—Fe1—C21 | 107.01 (10) |
C5—C4—H4B | 108.7 | C20—Fe1—C21 | 40.95 (10) |
C3—C4—H4B | 108.7 | C19—Fe1—C21 | 68.70 (10) |
H4A—C4—H4B | 107.6 | C13—Fe1—C21 | 158.13 (10) |
C4—C5—C6 | 113.2 (2) | C12—Fe1—C15 | 68.85 (9) |
C4—C5—H5A | 108.9 | C16—Fe1—C15 | 41.00 (9) |
C6—C5—H5A | 108.9 | C20—Fe1—C15 | 105.66 (10) |
C4—C5—H5B | 108.9 | C19—Fe1—C15 | 119.31 (10) |
C6—C5—H5B | 108.9 | C13—Fe1—C15 | 68.40 (10) |
H5A—C5—H5B | 107.7 | C21—Fe1—C15 | 123.76 (10) |
C7—C6—C5 | 113.7 (2) | C12—Fe1—C14 | 68.63 (9) |
C7—C6—H6A | 108.8 | C16—Fe1—C14 | 68.75 (10) |
C5—C6—H6A | 108.8 | C20—Fe1—C14 | 122.80 (10) |
C7—C6—H6B | 108.8 | C19—Fe1—C14 | 106.35 (10) |
C5—C6—H6B | 108.8 | C13—Fe1—C14 | 40.49 (10) |
H6A—C6—H6B | 107.7 | C21—Fe1—C14 | 160.00 (10) |
C6—C7—C8 | 113.1 (2) | C15—Fe1—C14 | 40.38 (10) |
C6—C7—H7A | 109.0 | C12—Fe1—C17 | 108.99 (10) |
C8—C7—H7A | 109.0 | C16—Fe1—C17 | 125.29 (10) |
C6—C7—H7B | 109.0 | C20—Fe1—C17 | 68.64 (10) |
C8—C7—H7B | 109.0 | C19—Fe1—C17 | 68.59 (10) |
H7A—C7—H7B | 107.8 | C13—Fe1—C17 | 122.84 (10) |
C7—C8—C9 | 113.7 (2) | C21—Fe1—C17 | 40.65 (10) |
C7—C8—H8A | 108.8 | C15—Fe1—C17 | 161.56 (10) |
C9—C8—H8A | 108.8 | C14—Fe1—C17 | 157.40 (10) |
C7—C8—H8B | 108.8 | C12—Fe1—C18 | 125.88 (10) |
C9—C8—H8B | 108.8 | C16—Fe1—C18 | 162.88 (10) |
H8A—C8—H8B | 107.7 | C20—Fe1—C18 | 68.53 (10) |
C10—C9—C8 | 111.6 (2) | C19—Fe1—C18 | 40.69 (10) |
C10—C9—H9A | 109.3 | C13—Fe1—C18 | 108.40 (10) |
C8—C9—H9A | 109.3 | C21—Fe1—C18 | 68.47 (10) |
C10—C9—H9B | 109.3 | C15—Fe1—C18 | 155.31 (10) |
C8—C9—H9B | 109.3 | C14—Fe1—C18 | 121.22 (10) |
H9A—C9—H9B | 108.0 | C17—Fe1—C18 | 40.69 (10) |
C11—C10—C9 | 114.5 (2) | C21—C17—C18 | 108.0 (2) |
C11—C10—H10A | 108.6 | C21—C17—Fe1 | 69.38 (14) |
C9—C10—H10A | 108.6 | C18—C17—Fe1 | 69.75 (14) |
C11—C10—H10B | 108.6 | C21—C17—H17 | 126.0 |
C9—C10—H10B | 108.6 | C18—C17—H17 | 126.0 |
H10A—C10—H10B | 107.6 | Fe1—C17—H17 | 126.4 |
O11—C11—C12 | 121.3 (2) | C19—C18—C17 | 108.0 (2) |
O11—C11—C10 | 122.3 (2) | C19—C18—Fe1 | 69.22 (14) |
C12—C11—C10 | 116.4 (2) | C17—C18—Fe1 | 69.56 (14) |
C13—C12—C16 | 108.0 (2) | C19—C18—H18 | 126.0 |
C13—C12—C11 | 125.5 (2) | C17—C18—H18 | 126.0 |
C16—C12—C11 | 126.3 (2) | Fe1—C18—H18 | 126.8 |
C13—C12—Fe1 | 69.88 (13) | C20—C19—C18 | 108.0 (2) |
C16—C12—Fe1 | 69.49 (13) | C20—C19—Fe1 | 69.38 (14) |
C11—C12—Fe1 | 122.06 (16) | C18—C19—Fe1 | 70.09 (14) |
C14—C13—C12 | 107.8 (2) | C20—C19—H19 | 126.0 |
C14—C13—Fe1 | 70.03 (14) | C18—C19—H19 | 126.0 |
C12—C13—Fe1 | 68.99 (13) | Fe1—C19—H19 | 126.1 |
C14—C13—H13 | 126.1 | C19—C20—C21 | 108.1 (2) |
C12—C13—H13 | 126.1 | C19—C20—Fe1 | 69.83 (14) |
Fe1—C13—H13 | 126.5 | C21—C20—Fe1 | 69.80 (14) |
C15—C14—C13 | 108.6 (2) | C19—C20—H20 | 126.0 |
C15—C14—Fe1 | 69.68 (14) | C21—C20—H20 | 126.0 |
C13—C14—Fe1 | 69.48 (13) | Fe1—C20—H20 | 126.0 |
C15—C14—H14 | 125.7 | C17—C21—C20 | 108.0 (2) |
C13—C14—H14 | 125.7 | C17—C21—Fe1 | 69.97 (13) |
Fe1—C14—H14 | 126.7 | C20—C21—Fe1 | 69.26 (13) |
C14—C15—C16 | 108.4 (2) | C17—C21—H21 | 126.0 |
C14—C15—Fe1 | 69.94 (14) | C20—C21—H21 | 126.0 |
C16—C15—Fe1 | 69.06 (13) | Fe1—C21—H21 | 126.3 |
D—H···A | D—H | H···A | D···A | D—H···A |
C17—H17···Br1i | 0.95 | 3.01 | 3.797 (3) | 142 |
C1—H1B···O11i | 0.99 | 2.55 | 3.422 (3) | 147 |
C14—H14···Cg2ii | 0.95 | 2.94 | 3.647 (3) | 133 |
Symmetry codes: (i) −x, −y+1, −z; (ii) −x+2, y−1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [Fe(C5H5)(C15H24BrO)] |
Mr | 433.20 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 85 |
a, b, c (Å) | 5.6027 (2), 9.8858 (4), 35.0048 (15) |
β (°) | 92.576 (2) |
V (Å3) | 1936.86 (13) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 2.85 |
Crystal size (mm) | 0.53 × 0.12 × 0.03 |
Data collection | |
Diffractometer | Bruker APEXII CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2004) |
Tmin, Tmax | 0.700, 0.918 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 37380, 7152, 5902 |
Rint | 0.041 |
(sin θ/λ)max (Å−1) | 0.800 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.050, 0.120, 1.22 |
No. of reflections | 7152 |
No. of parameters | 217 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.97, −2.43 |
Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SAINT, SHELXS97 (Sheldrick, 1997) and TITAN2000 (Hunter & Simpson, 1999), SHELXL97 (Sheldrick, 1997) and TITAN2000, ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006), SHELXL97, enCIFer (Allen et al., 2004), PLATON (Spek, 2003) and PARST (Nardelli, 1995).
D—H···A | D—H | H···A | D···A | D—H···A |
C17—H17···Br1i | 0.95 | 3.01 | 3.797 (3) | 142 |
C1—H1B···O11i | 0.99 | 2.55 | 3.422 (3) | 147 |
C14—H14···Cg2ii | 0.95 | 2.94 | 3.647 (3) | 133 |
Symmetry codes: (i) −x, −y+1, −z; (ii) −x+2, y−1/2, −z+1/2. |
The title compound, (I), is a useful precursor for the preparation of amino ferrocenyl derivatives (McAdam et al., 2000) or redox active surfactant systems (Saji et al., 2000) and its structure is reported here (Fig. 1). The cyclopentadienyl rings of the ferrocene are approximately eclipsed, with a mean Cm—Cg1—Cg2—Cn torsion angle of 4.2 (2)° (Cg1 and Cg2 are the centroids of the cyclopentadienyl rings, m = 12–16 and n = 17–21). The dihedral angle between the Cp ring mean planes is 4.68 (15)°. The ten-membered methylene chain of the undecanone substituent is nicely ordered and is bowed significantly towards the Fe atom. While the C11 atom lies 0.070 (3) Å above the C12···C16 ring plane, atom C1 is 0.735 (5) Å below that plane in the direction of the Fe1 atom.
In the crystal structure molecules of (I) link in a head-to-tail fashion through C17—H17···Br1 and C1···H1B···O11 hydrogen bonds to form inversion related dimers (Fig 2, Table 1). Then, C14—H14···Cg2 interactions link the dimers into an extended zigzag chain along the c axis (Fig. 3).