Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805030473/lh6507sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805030473/lh6507Isup2.hkl |
CCDC reference: 287639
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.002 Å
- Disorder in main residue
- R factor = 0.025
- wR factor = 0.069
- Data-to-parameter ratio = 14.6
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98 PLAT301_ALERT_3_C Main Residue Disorder ......................... 18.00 Perc. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 3
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 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 1 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion
The title complex was prepared by adapting the method of El Mouattasim et al. (1994) except that (η5-C5H5)Fe(CO)2Me and butyllithium were substituted for (η5-C5H5)Mo(CO)3Me and sec-butyllithium. Single crystals suitable for X-ray diffraction were grown from CH2Cl2/hexane. IR vCO (CH2Cl2, cm−1): 2059 (vs), 1998 (vs); 1H NMR (CDCl3, p.p.m.): 5.31 (s, 2H, CpH), 4.86 (s, 2H, CpH), 0.28 (s, 3H, Me).
The H atoms attached to aromatic C atoms were positioned geometrically and allowed to ride on parent atoms during refinement, with C—H = 0.95 Å and Uiso(H) = 1.2Ueq(C). The disordered methyl H atoms were accounted for using a two-site model, in which the H atoms were placed geometrically and allowed to ride, with C—H = 0.98 Å and Uiso(H) = 1.5Ueq(C).
Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL and ORTEP-3 (Farrugia, 1999); software used to prepare material for publication: SHELXTL.
[Fe(CH3)(C6H5O2)(CO)2] | F(000) = 480 |
Mr = 236.00 | Dx = 1.657 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 830 reflections |
a = 7.6183 (15) Å | θ = 2.6–30.2° |
b = 10.714 (2) Å | µ = 1.58 mm−1 |
c = 12.039 (2) Å | T = 173 K |
β = 105.661 (4)° | Block, brown |
V = 946.2 (3) Å3 | 0.24 × 0.19 × 0.19 mm |
Z = 4 |
Bruker SMART 1K CCD diffractometer | 2276 independent reflections |
Radiation source: fine-focus sealed tube | 1978 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
ϕ and ω scans | θmax = 28.0°, θmin = 2.6° |
Absorption correction: multi-scan (SADABS; Bruker, 1999) | h = −10→9 |
Tmin = 0.704, Tmax = 0.754 | k = −13→14 |
6617 measured reflections | l = −11→15 |
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)] = 0.025 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.070 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0402P)2 + 0.1317P] where P = (Fo2 + 2Fc2)/3 |
2276 reflections | (Δ/σ)max = 0.034 |
156 parameters | Δρmax = 0.31 e Å−3 |
8 restraints | Δρmin = −0.30 e Å−3 |
[Fe(CH3)(C6H5O2)(CO)2] | V = 946.2 (3) Å3 |
Mr = 236.00 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.6183 (15) Å | µ = 1.58 mm−1 |
b = 10.714 (2) Å | T = 173 K |
c = 12.039 (2) Å | 0.24 × 0.19 × 0.19 mm |
β = 105.661 (4)° |
Bruker SMART 1K CCD diffractometer | 2276 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1999) | 1978 reflections with I > 2σ(I) |
Tmin = 0.704, Tmax = 0.754 | Rint = 0.024 |
6617 measured reflections |
R[F2 > 2σ(F2)] = 0.025 | 8 restraints |
wR(F2) = 0.070 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.31 e Å−3 |
2276 reflections | Δρmin = −0.30 e Å−3 |
156 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 | Occ. (<1) | |
C2 | 0.556 (2) | 0.2166 (12) | 0.1394 (13) | 0.039 (2) | 0.551 (5) |
H2A | 0.6448 | 0.2205 | 0.0938 | 0.059* | 0.551 (5) |
H2B | 0.5549 | 0.2964 | 0.1790 | 0.059* | 0.551 (5) |
H2C | 0.4347 | 0.1998 | 0.0884 | 0.059* | 0.551 (5) |
C1 | 0.4782 (19) | −0.0213 (14) | 0.1556 (13) | 0.0298 (17) | 0.551 (5) |
O3 | 0.3807 (4) | −0.0845 (2) | 0.0875 (2) | 0.0456 (9) | 0.551 (5) |
C1' | 0.580 (3) | 0.2079 (15) | 0.1612 (15) | 0.035 (2) | 0.449 (5) |
O3' | 0.5522 (5) | 0.2868 (3) | 0.0945 (3) | 0.0536 (12) | 0.449 (5) |
C2' | 0.473 (3) | −0.0340 (19) | 0.1368 (17) | 0.035 (3) | 0.449 (5) |
H2'1 | 0.5479 | −0.0696 | 0.0900 | 0.052* | 0.449 (5) |
H2'2 | 0.3730 | 0.0144 | 0.0872 | 0.052* | 0.449 (5) |
H2'3 | 0.4229 | −0.1015 | 0.1738 | 0.052* | 0.449 (5) |
C3 | 0.4404 (2) | 0.11550 (19) | 0.31256 (15) | 0.0366 (4) | |
C4 | 0.89004 (19) | 0.03310 (16) | 0.25142 (12) | 0.0247 (3) | |
C5 | 0.8231 (2) | −0.06350 (14) | 0.31040 (14) | 0.0271 (3) | |
H5 | 0.8071 | −0.1485 | 0.2876 | 0.033* | |
C6 | 0.7851 (2) | −0.01092 (17) | 0.40820 (13) | 0.0313 (4) | |
H6 | 0.7373 | −0.0542 | 0.4625 | 0.038* | |
C7 | 0.8300 (2) | 0.11786 (18) | 0.41208 (14) | 0.0335 (4) | |
H7 | 0.8179 | 0.1755 | 0.4695 | 0.040* | |
C8 | 0.8956 (2) | 0.14543 (16) | 0.31631 (14) | 0.0319 (4) | |
H8 | 0.9363 | 0.2247 | 0.2980 | 0.038* | |
C9 | 0.9399 (2) | 0.01941 (15) | 0.14299 (13) | 0.0244 (3) | |
O1 | 0.99336 (18) | 0.11962 (11) | 0.10201 (11) | 0.0339 (3) | |
H1 | 1.0160 | 0.1032 | 0.0391 | 0.051* | |
O2 | 0.93037 (18) | −0.08486 (10) | 0.09565 (11) | 0.0329 (3) | |
O5 | 0.3221 (2) | 0.13996 (19) | 0.34747 (14) | 0.0649 (5) | |
Fe | 0.62709 (3) | 0.07778 (2) | 0.257978 (18) | 0.02464 (9) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C2 | 0.051 (5) | 0.039 (4) | 0.030 (5) | 0.003 (3) | 0.014 (4) | 0.001 (2) |
C1 | 0.028 (3) | 0.036 (3) | 0.024 (4) | 0.003 (2) | 0.003 (2) | −0.001 (2) |
O3 | 0.0418 (16) | 0.0463 (16) | 0.0384 (15) | −0.0099 (11) | −0.0066 (12) | −0.0078 (11) |
C1' | 0.039 (4) | 0.042 (4) | 0.027 (5) | 0.014 (3) | 0.016 (4) | 0.006 (3) |
O3' | 0.076 (3) | 0.048 (2) | 0.042 (2) | 0.0259 (18) | 0.0256 (17) | 0.0233 (16) |
C2' | 0.037 (4) | 0.041 (5) | 0.024 (5) | −0.008 (3) | 0.003 (3) | −0.004 (3) |
C3 | 0.0292 (8) | 0.0505 (11) | 0.0298 (8) | 0.0045 (8) | 0.0073 (7) | 0.0034 (8) |
C4 | 0.0214 (7) | 0.0279 (8) | 0.0255 (7) | 0.0001 (6) | 0.0076 (6) | −0.0002 (6) |
C5 | 0.0265 (8) | 0.0267 (8) | 0.0278 (8) | 0.0030 (6) | 0.0067 (6) | 0.0040 (6) |
C6 | 0.0271 (8) | 0.0438 (10) | 0.0224 (8) | 0.0030 (7) | 0.0058 (6) | 0.0066 (7) |
C7 | 0.0280 (8) | 0.0457 (10) | 0.0267 (8) | −0.0036 (7) | 0.0072 (6) | −0.0103 (7) |
C8 | 0.0293 (8) | 0.0326 (9) | 0.0365 (9) | −0.0078 (7) | 0.0132 (7) | −0.0084 (7) |
C9 | 0.0204 (7) | 0.0263 (8) | 0.0273 (7) | 0.0023 (6) | 0.0081 (6) | 0.0020 (6) |
O1 | 0.0452 (7) | 0.0276 (6) | 0.0358 (6) | −0.0043 (5) | 0.0227 (5) | −0.0004 (5) |
O2 | 0.0459 (7) | 0.0241 (6) | 0.0342 (6) | 0.0045 (5) | 0.0200 (6) | 0.0004 (5) |
O5 | 0.0393 (8) | 0.1098 (15) | 0.0507 (9) | 0.0129 (9) | 0.0209 (7) | 0.0090 (9) |
Fe | 0.02289 (13) | 0.03106 (14) | 0.02088 (13) | 0.00366 (8) | 0.00746 (9) | 0.00159 (8) |
C2—Fe | 2.031 (8) | C4—C9 | 1.462 (2) |
C2—H2A | 0.9800 | C4—Fe | 2.0818 (15) |
C2—H2B | 0.9800 | C5—C6 | 1.404 (2) |
C2—H2C | 0.9800 | C5—Fe | 2.1002 (16) |
C1—O3 | 1.164 (7) | C5—H5 | 0.9500 |
C1—Fe | 1.782 (7) | C6—C7 | 1.419 (3) |
C1'—O3' | 1.146 (7) | C6—Fe | 2.1088 (16) |
C1'—Fe | 1.790 (8) | C6—H6 | 0.9500 |
C2'—Fe | 2.004 (9) | C7—C8 | 1.406 (2) |
C2'—H2'1 | 0.9800 | C7—Fe | 2.1138 (17) |
C2'—H2'2 | 0.9800 | C7—H7 | 0.9500 |
C2'—H2'3 | 0.9800 | C8—Fe | 2.1040 (16) |
C3—O5 | 1.124 (2) | C8—H8 | 0.9500 |
C3—Fe | 1.7670 (19) | C9—O2 | 1.2472 (19) |
C4—C5 | 1.425 (2) | C9—O1 | 1.2926 (19) |
C4—C8 | 1.429 (2) | O1—H1 | 0.8400 |
Fe—C2—H2A | 109.5 | O1—C9—C4 | 116.23 (14) |
Fe—C2—H2B | 109.5 | C9—O1—H1 | 109.5 |
H2A—C2—H2B | 109.5 | C3—Fe—C1 | 88.1 (6) |
Fe—C2—H2C | 109.5 | C3—Fe—C1' | 91.4 (6) |
H2A—C2—H2C | 109.5 | C1—Fe—C1' | 92.1 (9) |
H2B—C2—H2C | 109.5 | C3—Fe—C2' | 92.0 (7) |
O3—C1—Fe | 178.9 (16) | C1—Fe—C2' | 4.0 (13) |
O3'—C1'—Fe | 176.1 (18) | C1'—Fe—C2' | 91.0 (10) |
Fe—C2'—H2'1 | 109.5 | C3—Fe—C2 | 90.3 (5) |
Fe—C2'—H2'2 | 109.5 | C1—Fe—C2 | 87.2 (8) |
H2'1—C2'—H2'2 | 109.5 | C1'—Fe—C2 | 4.9 (12) |
Fe—C2'—H2'3 | 109.5 | C2'—Fe—C2 | 86.2 (9) |
H2'1—C2'—H2'3 | 109.5 | C3—Fe—C4 | 161.09 (7) |
H2'2—C2'—H2'3 | 109.5 | C1—Fe—C4 | 106.0 (5) |
O5—C3—Fe | 179.7 (2) | C1'—Fe—C4 | 100.3 (6) |
C5—C4—C8 | 107.52 (14) | C2'—Fe—C4 | 102.4 (7) |
C5—C4—C9 | 125.88 (15) | C2—Fe—C4 | 102.6 (5) |
C8—C4—C9 | 126.59 (15) | C3—Fe—C5 | 129.16 (8) |
C5—C4—Fe | 70.77 (9) | C1—Fe—C5 | 92.7 (5) |
C8—C4—Fe | 70.87 (9) | C1'—Fe—C5 | 139.2 (6) |
C9—C4—Fe | 122.78 (10) | C2'—Fe—C5 | 91.0 (7) |
C6—C5—C4 | 108.00 (14) | C2—Fe—C5 | 140.5 (5) |
C6—C5—Fe | 70.84 (9) | C4—Fe—C5 | 39.84 (6) |
C4—C5—Fe | 69.38 (9) | C3—Fe—C8 | 127.20 (8) |
C6—C5—H5 | 126.0 | C1—Fe—C8 | 144.7 (6) |
C4—C5—H5 | 126.0 | C1'—Fe—C8 | 87.4 (7) |
Fe—C5—H5 | 125.4 | C2'—Fe—C8 | 140.7 (7) |
C5—C6—C7 | 108.36 (14) | C2—Fe—C8 | 91.9 (5) |
C5—C6—Fe | 70.18 (9) | C4—Fe—C8 | 39.93 (6) |
C7—C6—Fe | 70.55 (9) | C5—Fe—C8 | 66.40 (6) |
C5—C6—H6 | 125.8 | C3—Fe—C6 | 96.57 (7) |
C7—C6—H6 | 125.8 | C1—Fe—C6 | 115.7 (6) |
Fe—C6—H6 | 125.0 | C1'—Fe—C6 | 151.2 (7) |
C8—C7—C6 | 108.26 (15) | C2'—Fe—C6 | 116.2 (7) |
C8—C7—Fe | 70.15 (9) | C2—Fe—C6 | 156.2 (5) |
C6—C7—Fe | 70.17 (9) | C4—Fe—C6 | 66.21 (6) |
C8—C7—H7 | 125.9 | C5—Fe—C6 | 38.98 (6) |
C6—C7—H7 | 125.9 | C8—Fe—C6 | 65.84 (7) |
Fe—C7—H7 | 125.4 | C3—Fe—C7 | 95.66 (8) |
C7—C8—C4 | 107.86 (15) | C1—Fe—C7 | 154.9 (6) |
C7—C8—Fe | 70.90 (9) | C1'—Fe—C7 | 112.5 (7) |
C4—C8—Fe | 69.20 (8) | C2'—Fe—C7 | 155.0 (7) |
C7—C8—H8 | 126.1 | C2—Fe—C7 | 117.4 (5) |
C4—C8—H8 | 126.1 | C4—Fe—C7 | 66.21 (6) |
Fe—C8—H8 | 125.4 | C5—Fe—C7 | 65.82 (7) |
O2—C9—O1 | 123.71 (15) | C8—Fe—C7 | 38.95 (6) |
O2—C9—C4 | 120.06 (14) | C6—Fe—C7 | 39.28 (7) |
C8—C4—C5—C6 | 1.11 (18) | C4—C5—Fe—C2' | 108.4 (7) |
C9—C4—C5—C6 | −177.69 (14) | C6—C5—Fe—C2 | 141.9 (8) |
Fe—C4—C5—C6 | −60.60 (11) | C4—C5—Fe—C2 | 23.2 (8) |
C8—C4—C5—Fe | 61.71 (11) | C6—C5—Fe—C4 | 118.70 (14) |
C9—C4—C5—Fe | −117.09 (15) | C6—C5—Fe—C8 | 80.21 (10) |
C4—C5—C6—C7 | −0.82 (18) | C4—C5—Fe—C8 | −38.50 (9) |
Fe—C5—C6—C7 | −60.49 (11) | C4—C5—Fe—C6 | −118.70 (14) |
C4—C5—C6—Fe | 59.68 (11) | C6—C5—Fe—C7 | 37.44 (10) |
C5—C6—C7—C8 | 0.20 (18) | C4—C5—Fe—C7 | −81.26 (10) |
Fe—C6—C7—C8 | −60.06 (12) | C7—C8—Fe—C3 | 42.07 (15) |
C5—C6—C7—Fe | 60.26 (11) | C4—C8—Fe—C3 | 160.67 (11) |
C6—C7—C8—C4 | 0.49 (19) | C7—C8—Fe—C1 | −138.3 (10) |
Fe—C7—C8—C4 | −59.58 (11) | C4—C8—Fe—C1 | −19.7 (10) |
C6—C7—C8—Fe | 60.07 (11) | C7—C8—Fe—C1' | 131.9 (7) |
C5—C4—C8—C7 | −0.99 (18) | C4—C8—Fe—C1' | −109.5 (7) |
C9—C4—C8—C7 | 177.80 (14) | C7—C8—Fe—C2' | −139.9 (11) |
Fe—C4—C8—C7 | 60.66 (12) | C4—C8—Fe—C2' | −21.3 (11) |
C5—C4—C8—Fe | −61.65 (11) | C7—C8—Fe—C2 | 133.9 (5) |
C9—C4—C8—Fe | 117.15 (15) | C4—C8—Fe—C2 | −107.5 (5) |
C5—C4—C9—O2 | −2.1 (2) | C7—C8—Fe—C4 | −118.60 (15) |
C8—C4—C9—O2 | 179.28 (15) | C7—C8—Fe—C5 | −80.18 (11) |
Fe—C4—C9—O2 | −91.13 (17) | C4—C8—Fe—C5 | 38.42 (9) |
C5—C4—C9—O1 | 178.23 (15) | C7—C8—Fe—C6 | −37.38 (11) |
C8—C4—C9—O1 | −0.3 (2) | C4—C8—Fe—C6 | 81.21 (11) |
Fe—C4—C9—O1 | 89.24 (16) | C4—C8—Fe—C7 | 118.60 (15) |
C5—C4—Fe—C3 | 62.8 (3) | C5—C6—Fe—C3 | 150.25 (11) |
C8—C4—Fe—C3 | −54.5 (3) | C7—C6—Fe—C3 | −90.91 (11) |
C9—C4—Fe—C3 | −176.3 (2) | C5—C6—Fe—C1 | 59.2 (6) |
C5—C4—Fe—C1 | −74.4 (6) | C7—C6—Fe—C1 | 178.0 (6) |
C8—C4—Fe—C1 | 168.3 (6) | C5—C6—Fe—C1' | −104.5 (14) |
C9—C4—Fe—C1 | 46.5 (7) | C7—C6—Fe—C1' | 14.3 (14) |
C5—C4—Fe—C1' | −169.6 (7) | C5—C6—Fe—C2' | 54.7 (8) |
C8—C4—Fe—C1' | 73.1 (7) | C7—C6—Fe—C2' | 173.5 (8) |
C9—C4—Fe—C1' | −48.7 (7) | C5—C6—Fe—C2 | −103.8 (13) |
C5—C4—Fe—C2' | −76.3 (7) | C7—C6—Fe—C2 | 15.1 (13) |
C8—C4—Fe—C2' | 166.4 (7) | C5—C6—Fe—C4 | −37.89 (9) |
C9—C4—Fe—C2' | 44.6 (8) | C7—C6—Fe—C4 | 80.95 (10) |
C5—C4—Fe—C2 | −165.1 (5) | C7—C6—Fe—C5 | 118.83 (14) |
C8—C4—Fe—C2 | 77.6 (5) | C5—C6—Fe—C8 | −81.77 (10) |
C9—C4—Fe—C2 | −44.2 (5) | C7—C6—Fe—C8 | 37.07 (9) |
C8—C4—Fe—C5 | −117.28 (13) | C5—C6—Fe—C7 | −118.83 (14) |
C9—C4—Fe—C5 | 120.91 (18) | C8—C7—Fe—C3 | −147.57 (12) |
C5—C4—Fe—C8 | 117.28 (13) | C6—C7—Fe—C3 | 93.47 (11) |
C9—C4—Fe—C8 | −121.81 (18) | C8—C7—Fe—C1 | 114.7 (14) |
C5—C4—Fe—C6 | 37.08 (10) | C6—C7—Fe—C1 | −4.2 (14) |
C8—C4—Fe—C6 | −80.20 (11) | C8—C7—Fe—C1' | −53.6 (7) |
C9—C4—Fe—C6 | 157.99 (16) | C6—C7—Fe—C1' | −172.6 (7) |
C5—C4—Fe—C7 | 80.19 (10) | C8—C7—Fe—C2' | 105.2 (16) |
C8—C4—Fe—C7 | −37.09 (10) | C6—C7—Fe—C2' | −13.8 (16) |
C9—C4—Fe—C7 | −158.91 (16) | C8—C7—Fe—C2 | −54.2 (6) |
C6—C5—Fe—C3 | −39.47 (14) | C6—C7—Fe—C2 | −173.2 (6) |
C4—C5—Fe—C3 | −158.18 (11) | C8—C7—Fe—C4 | 38.01 (10) |
C6—C5—Fe—C1 | −129.2 (6) | C6—C7—Fe—C4 | −80.95 (10) |
C4—C5—Fe—C1 | 112.1 (6) | C8—C7—Fe—C5 | 81.80 (11) |
C6—C5—Fe—C1' | 134.5 (11) | C6—C7—Fe—C5 | −37.16 (9) |
C4—C5—Fe—C1' | 15.8 (11) | C6—C7—Fe—C8 | −118.96 (15) |
C6—C5—Fe—C2' | −132.9 (7) | C8—C7—Fe—C6 | 118.96 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.84 | 1.79 | 2.6240 (19) | 174 |
Symmetry code: (i) −x+2, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | [Fe(CH3)(C6H5O2)(CO)2] |
Mr | 236.00 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 173 |
a, b, c (Å) | 7.6183 (15), 10.714 (2), 12.039 (2) |
β (°) | 105.661 (4) |
V (Å3) | 946.2 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.58 |
Crystal size (mm) | 0.24 × 0.19 × 0.19 |
Data collection | |
Diffractometer | Bruker SMART 1K CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 1999) |
Tmin, Tmax | 0.704, 0.754 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6617, 2276, 1978 |
Rint | 0.024 |
(sin θ/λ)max (Å−1) | 0.661 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.025, 0.070, 1.08 |
No. of reflections | 2276 |
No. of parameters | 156 |
No. of restraints | 8 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.31, −0.30 |
Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SAINT, SHELXTL (Bruker, 1999), SHELXL97 (Sheldrick, 1997), SHELXTL and ORTEP-3 (Farrugia, 1999), SHELXTL.
C2—Fe | 2.031 (8) | C2'—Fe | 2.004 (9) |
C1—O3 | 1.164 (7) | C3—O5 | 1.124 (2) |
C1—Fe | 1.782 (7) | C3—Fe | 1.7670 (19) |
C1'—O3' | 1.146 (7) | C9—O2 | 1.2472 (19) |
C1'—Fe | 1.790 (8) | C9—O1 | 1.2926 (19) |
O3—C1—Fe | 178.9 (16) | C3—Fe—C1 | 88.1 (6) |
O3'—C1'—Fe | 176.1 (18) | C3—Fe—C2 | 90.3 (5) |
O5—C3—Fe | 179.7 (2) | C1—Fe—C2 | 87.2 (8) |
O2—C9—O1 | 123.71 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.84 | 1.79 | 2.6240 (19) | 174 |
Symmetry code: (i) −x+2, −y, −z. |
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Group six analogs of the title complex have been prepared (El Mouattasim et al., 1994) with the aim of utilizing the functional carboxylic acid group as labeling agents for amino acids. We prepared the title compound, (I), as part of our interest in solvent-free solid–gas reactions. It was envisaged that the network of hydrogen bonding between neighbouring molecules via the carboxylic acid functionality will serve as channels for small gaseous molecules to permeate into the crystal lattice (Braga et al., 2002; Fig. 2). Preliminary studies with SO2 have indicated otherwise, indicating that intramolecular forces, such as steric interactions between ligands bonded to the central metal atom may be more crucial in influencing the single-crystal/gas reactivity (Munyaneza et al., 2005).
In the title compound, the Fe(CO)2Me leg of the tripodal piano stool is characterized by a disordered Me group which was refined over positions C2 and C2'. These are located on opposite sides of a local psuedo-mirror plane running through the carboxylic acid functionality and the central Fe metal with 50% occupancy of each site (Fig. 1). Mousser et al. (1996) have prepared four-legged piano stool tungsten analogs of the title complex, and it is interesting to note that the Me group was similarly disordered between two trans positions in syn and anti configurations relative to the carboxylic acid functional group. In the crystal structure, molecules form the expected centrosymmetric dimers via O—H···O hydrogen bonds (Table 1 and Fig. 2).