Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801003804/wn6006sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801003804/wn6006Isup2.hkl |
CCDC reference: 162794
Key indicators
- Single-crystal X-ray study
- T = 297 K
- Mean (C-C) = 0.004 Å
- R factor = 0.041
- wR factor = 0.105
- Data-to-parameter ratio = 18.5
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry General Notes
ABSTM_02 When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 1.104 Tmax scaled 0.823 Tmin scaled 0.753
To a mixture of 2-(chlorophenyl)benzimidazole (2.5 g, 10 mmol) and K2CO3 (2.07 g, 15 mmol) in CH3CN (100 ml) was added (trimethyl)ammoniumferrocenylmethyl iodide (4.05 g, 10.5 mmol) (Pauson et al., 1966; Ferguson et al., 1994a), and the mixture was refluxed for 12 h. The reaction was cooled to room temperature, water added and the suspension extracted into CHCl3. The organic layer was washed with water, dried (MgSO4) and evaporated under vacuum to leave a brown solid. The crude product was purified by column chromatography on silica gel using CH2Cl2–CH3OH (97:3) as eluent. The title compound was obtained as a light-brown powder. Yield 2.8 g (64%), m.p. 435–438 K (uncorrected). Analysis for C24H19ClFeN2, calculated: C 67.57, H 4.45, N 6.56%; found: C 67.47, H 4.51, N 6.52%. IR (KBr, ν cm-1), 3051, 2971, 2308, 1708, 1639, 1456, 1422, 1364, 1330, 1261, 1153, 1101, 1027, 1008, 895, 741, 706, 695. 1H NMR [400 MHz, δH (p.p.m.), CDCl3], 7.82 (m, 2H, aryl-H), 7.69 (m, 1H, C6H4), 7.56–7.48 (m, 3H, aryl-H and C6H4), 7.34 (m, 2H, C6H4), 5.22 (s, 2H, Fc—CH2), 4.13–4.07 (M, 9H, Fc—H). 13C NMR (δC, CDCl3), 152.27, 143.27, 136.04, 135.08, 132.79, 130.4, 130.35, 130.08, 128.21, 123.49, 123.05, 120.48, 110.86, 83.36, 69.25, 69.14, 68.71, 44.95.
All H atoms bound to C atoms were treated as riding, with SHELXL97 (Sheldrick, 1997) defaults for C—H distances and with Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C) for the remainder. Examination of the structure with PLATON (Spek, 1998) showed that there were no solvent-accessible voids in the crystal lattice.
Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and PLATON (Spek, 1998); software used to prepare material for publication: SHELXL97 and PREP8 (Ferguson, 1998).
Fig. 1. A view of (I) with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. |
[Fe(C5H5)(C19H14ClN2)] | Dx = 1.46 Mg m−3 |
Mr = 426.71 | Melting point: 437 K |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 11.6838 (9) Å | Cell parameters from 27 reflections |
b = 9.9220 (6) Å | θ = 4.5–16.1° |
c = 16.7493 (14) Å | µ = 0.93 mm−1 |
β = 90.542 (6)° | T = 297 K |
V = 1941.6 (2) Å3 | Block, orange |
Z = 4 | 0.37 × 0.24 × 0.21 mm |
F(000) = 880 |
Bruker P4 diffractometer | 3646 reflections with I > 2σ(I) |
Radiation source: X-ray tube | Rint = 0.033 |
Graphite monochromator | θmax = 28.0°, θmin = 2.1° |
ω–2θ scans | h = −15→1 |
Absorption correction: ψ scan (North et al., 1968) | k = −13→1 |
Tmin = 0.682, Tmax = 0.746 | l = −22→22 |
5483 measured reflections | 3 standard reflections every 197 reflections |
4669 independent reflections | intensity decay: 2% |
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) = 0.105 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0495P)2 + 0.6062P] where P = (Fo2 + 2Fc2)/3 |
4669 reflections | (Δ/σ)max < 0.001 |
253 parameters | Δρmax = 0.70 e Å−3 |
0 restraints | Δρmin = −0.55 e Å−3 |
[Fe(C5H5)(C19H14ClN2)] | V = 1941.6 (2) Å3 |
Mr = 426.71 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 11.6838 (9) Å | µ = 0.93 mm−1 |
b = 9.9220 (6) Å | T = 297 K |
c = 16.7493 (14) Å | 0.37 × 0.24 × 0.21 mm |
β = 90.542 (6)° |
Bruker P4 diffractometer | 3646 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.033 |
Tmin = 0.682, Tmax = 0.746 | 3 standard reflections every 197 reflections |
5483 measured reflections | intensity decay: 2% |
4669 independent reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.105 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.70 e Å−3 |
4669 reflections | Δρmin = −0.55 e Å−3 |
253 parameters |
Geometry. Mean plane data ex-SHELXL97 for compound (I) ################################################################# Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 2.8856(0.0125)x + 8.7907(0.0034)y + 6.5342(0.0116)z = 8.2081(0.0140) * 0.0410 (0.0012) C1 * -0.0613 (0.0011) N1 * 0.0862 (0.0014) N2 * -0.0656 (0.0008) C2 * -0.0003 (0.0006) C3 - 0.0682 (0.0026) C4 - 2.8098 (0.0030) Fe1 - 2.0934 (0.0061) Cl1 Rms deviation of fitted atoms = 0.0586 11.1300(0.0039)x - 0.2023(0.0106)y - 5.2347(0.0169)z = 11.9425(0.0065) Angle to previous plane (with approximate e.s.d.) = 84.37 (9) * 0.0010 (0.0013) C11 * -0.0009 (0.0013) C12 * 0.0005 (0.0014) C13 * 0.0002 (0.0014) C14 * -0.0007 (0.0013) C15 - 1.6466 (0.0010) Fe1 - 4.8199 (0.0055) Cl1 0.5014 (0.0057) N1 0.5217 (0.0040) N2 Rms deviation of fitted atoms = 0.0007 11.1763(0.0044)x - 0.1369(0.0130)y - 5.0289(0.0198)z = 8.7321(0.0072) Angle to previous plane (with approximate e.s.d.) = 0.83 (9) * -0.0003 (0.0016) C21 * 0.0019 (0.0016) C22 * -0.0027 (0.0016) C23 * 0.0024 (0.0015) C24 * -0.0013 (0.0016) C25 1.6480 (0.0011) Fe1 - 1.4702 (0.0065) Cl1 3.8641 (0.0067) N1 3.8669 (0.0047) N2 Rms deviation of fitted atoms = 0.0019 4.6333(0.0105)x + 1.1270(0.0100)y + 15.1943(0.0071)z = 11.1411(0.0082) Angle to previous plane (with approximate e.s.d.) = 83.54 (8) * -0.0048 (0.0016) C31 * -0.0008 (0.0018) C32 * 0.0027 (0.0019) C33 * 0.0012 (0.0018) C34 * -0.0068 (0.0018) C35 * 0.0086 (0.0016) C36 - 4.4427 (0.0021) Fe1 - 0.0685 (0.0034) Cl1 0.8866 (0.0039) N1 - 0.8935 (0.0040) N2 Rms deviation of fitted atoms = 0.0050 11.1300(0.0039)x - 0.2023(0.0106)y - 5.2347(0.0169)z = 11.9425(0.0065) Angle to previous plane (with approximate e.s.d.) = 84.32 (7) * 0.0010 (0.0013) C11 * -0.0009 (0.0013) C12 * 0.0005 (0.0014) C13 * 0.0002 (0.0014) C14 * -0.0007 (0.0013) C15 - 1.6466 (0.0010) Fe1 Rms deviation of fitted atoms = 0.0007 4.6333(0.0105)x + 1.1270(0.0100)y + 15.1943(0.0071)z = 11.1411(0.0082) Angle to previous plane (with approximate e.s.d.) = 84.32 (7) * -0.0048 (0.0016) C31 * -0.0008 (0.0018) C32 * 0.0027 (0.0019) C33 * 0.0012 (0.0018) C34 * -0.0068 (0.0018) C35 * 0.0086 (0.0016) C36 - 4.4427 (0.0021) Fe1 - 0.0685 (0.0034) Cl1 0.8866 (0.0039) N1 - 0.8935 (0.0040) N2 Rms deviation of fitted atoms = 0.0050 2.8856(0.0125)x + 8.7907(0.0034)y + 6.5342(0.0116)z = 8.2081(0.0140) Angle to previous plane (with approximate e.s.d.) = 56.21 (8) * 0.0410 (0.0012) C1 * -0.0613 (0.0011) N1 * 0.0862 (0.0014) N2 * -0.0656 (0.0008) C2 * -0.0003 (0.0006) C3 - 0.0682 (0.0026) C4 - 2.8098 (0.0030) Fe1 - 2.0934 (0.0061) Cl1 Rms deviation of fitted atoms = 0.0586 11.1300(0.0039)x - 0.2023(0.0106)y - 5.2347(0.0169)z = 11.9425(0.0065) Angle to previous plane (with approximate e.s.d.) = 84.37 (9) * 0.0010 (0.0013) C11 * -0.0009 (0.0013) C12 * 0.0005 (0.0014) C13 * 0.0002 (0.0014) C14 * -0.0007 (0.0013) C15 - 1.6466 (0.0010) Fe1 - 4.8199 (0.0055) Cl1 0.5014 (0.0057) N1 0.5217 (0.0040) N2 Rms deviation of fitted atoms = 0.0007 |
x | y | z | Uiso*/Ueq | ||
Fe1 | 0.98748 (2) | 0.19694 (3) | 0.125118 (17) | 0.04373 (10) | |
Cl1 | 0.85839 (6) | 0.07059 (8) | 0.46174 (5) | 0.0889 (2) | |
N1 | 1.30022 (14) | 0.21830 (17) | 0.37891 (10) | 0.0485 (4) | |
N2 | 1.25195 (13) | 0.33341 (16) | 0.26794 (10) | 0.0416 (3) | |
C1 | 1.21910 (16) | 0.28455 (18) | 0.34126 (12) | 0.0421 (4) | |
C2 | 1.18019 (17) | 0.38725 (19) | 0.20396 (12) | 0.0454 (4) | |
C3 | 1.36474 (15) | 0.29349 (19) | 0.25859 (12) | 0.0439 (4) | |
C4 | 1.39374 (17) | 0.2243 (2) | 0.32843 (13) | 0.0475 (5) | |
C5 | 1.50397 (19) | 0.1720 (3) | 0.33798 (17) | 0.0622 (6) | |
C6 | 1.5807 (2) | 0.1918 (3) | 0.2781 (2) | 0.0744 (8) | |
C7 | 1.5508 (2) | 0.2614 (3) | 0.2087 (2) | 0.0748 (8) | |
C8 | 1.4415 (2) | 0.3124 (2) | 0.19671 (16) | 0.0601 (6) | |
C11 | 1.14627 (15) | 0.28015 (19) | 0.14477 (12) | 0.0418 (4) | |
C12 | 1.14919 (17) | 0.1385 (2) | 0.15682 (14) | 0.0492 (5) | |
C13 | 1.11425 (18) | 0.0742 (2) | 0.08476 (15) | 0.0585 (6) | |
C14 | 1.08948 (19) | 0.1749 (3) | 0.02825 (14) | 0.0581 (6) | |
C15 | 1.10874 (18) | 0.3024 (2) | 0.06444 (13) | 0.0513 (5) | |
C21 | 0.8768 (2) | 0.2774 (4) | 0.2048 (2) | 0.0798 (9) | |
C22 | 0.8794 (2) | 0.1419 (4) | 0.21387 (16) | 0.0776 (8) | |
C23 | 0.8466 (2) | 0.0813 (3) | 0.14345 (19) | 0.0749 (8) | |
C24 | 0.82292 (19) | 0.1806 (4) | 0.08709 (17) | 0.0833 (10) | |
C25 | 0.8419 (2) | 0.3069 (3) | 0.1267 (3) | 0.0937 (12) | |
C31 | 1.10316 (17) | 0.3059 (2) | 0.37384 (12) | 0.0454 (4) | |
C32 | 1.0548 (2) | 0.4329 (2) | 0.37944 (14) | 0.0580 (5) | |
C33 | 0.9467 (2) | 0.4477 (3) | 0.41151 (16) | 0.0688 (7) | |
C34 | 0.8862 (2) | 0.3376 (3) | 0.43803 (15) | 0.0659 (6) | |
C35 | 0.93509 (19) | 0.2121 (2) | 0.43191 (14) | 0.0568 (5) | |
C36 | 1.04353 (18) | 0.1948 (2) | 0.40115 (13) | 0.0506 (5) | |
H2A | 1.2214 | 0.4582 | 0.1766 | 0.055* | |
H2B | 1.1118 | 0.4266 | 0.2267 | 0.055* | |
H5 | 1.5246 | 0.1249 | 0.3839 | 0.075* | |
H6 | 1.6546 | 0.1581 | 0.2838 | 0.089* | |
H7 | 1.6056 | 0.2740 | 0.1695 | 0.090* | |
H8 | 1.4207 | 0.3568 | 0.1499 | 0.072* | |
H12 | 1.1704 | 0.0951 | 0.2039 | 0.059* | |
H13 | 1.1088 | −0.0183 | 0.0765 | 0.070* | |
H14 | 1.0647 | 0.1606 | −0.0240 | 0.070* | |
H15 | 1.0987 | 0.3859 | 0.0401 | 0.062* | |
H21 | 0.8952 | 0.3404 | 0.2440 | 0.096* | |
H22 | 0.9002 | 0.0967 | 0.2605 | 0.093* | |
H23 | 0.8411 | −0.0111 | 0.1349 | 0.090* | |
H24 | 0.7995 | 0.1677 | 0.0344 | 0.100* | |
H25 | 0.8328 | 0.3922 | 0.1045 | 0.112* | |
H32 | 1.0947 | 0.5080 | 0.3617 | 0.070* | |
H33 | 0.9146 | 0.5332 | 0.4152 | 0.083* | |
H34 | 0.8137 | 0.3479 | 0.4597 | 0.079* | |
H36 | 1.0760 | 0.1093 | 0.3988 | 0.061* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe1 | 0.03316 (15) | 0.04911 (17) | 0.04894 (17) | −0.00090 (11) | 0.00201 (11) | −0.00238 (13) |
Cl1 | 0.0661 (4) | 0.0896 (5) | 0.1116 (6) | −0.0184 (4) | 0.0282 (4) | 0.0133 (4) |
N1 | 0.0443 (9) | 0.0493 (10) | 0.0520 (9) | 0.0046 (7) | −0.0030 (7) | −0.0052 (8) |
N2 | 0.0342 (7) | 0.0401 (8) | 0.0505 (9) | −0.0016 (6) | 0.0016 (6) | −0.0032 (7) |
C1 | 0.0381 (9) | 0.0387 (9) | 0.0493 (10) | −0.0019 (7) | 0.0024 (8) | −0.0085 (8) |
C2 | 0.0429 (10) | 0.0381 (9) | 0.0553 (11) | 0.0002 (8) | −0.0001 (8) | 0.0028 (8) |
C3 | 0.0327 (8) | 0.0386 (9) | 0.0603 (12) | −0.0037 (7) | 0.0028 (8) | −0.0110 (9) |
C4 | 0.0377 (9) | 0.0429 (10) | 0.0618 (12) | 0.0001 (8) | −0.0040 (8) | −0.0133 (9) |
C5 | 0.0425 (11) | 0.0595 (14) | 0.0843 (17) | 0.0058 (10) | −0.0119 (11) | −0.0129 (12) |
C6 | 0.0371 (11) | 0.0716 (17) | 0.115 (2) | 0.0059 (11) | 0.0012 (13) | −0.0200 (16) |
C7 | 0.0457 (12) | 0.0714 (16) | 0.108 (2) | −0.0093 (12) | 0.0293 (14) | −0.0203 (16) |
C8 | 0.0494 (12) | 0.0554 (13) | 0.0757 (15) | −0.0064 (10) | 0.0159 (11) | −0.0065 (11) |
C11 | 0.0325 (8) | 0.0439 (10) | 0.0490 (10) | 0.0012 (7) | 0.0037 (7) | 0.0019 (8) |
C12 | 0.0431 (10) | 0.0413 (10) | 0.0631 (12) | 0.0062 (8) | −0.0076 (9) | −0.0006 (9) |
C13 | 0.0471 (11) | 0.0510 (12) | 0.0773 (15) | 0.0058 (9) | −0.0005 (10) | −0.0187 (11) |
C14 | 0.0454 (11) | 0.0792 (16) | 0.0498 (11) | −0.0018 (11) | 0.0055 (9) | −0.0130 (11) |
C15 | 0.0429 (10) | 0.0619 (13) | 0.0493 (11) | −0.0005 (9) | 0.0045 (8) | 0.0084 (10) |
C21 | 0.0426 (12) | 0.103 (2) | 0.094 (2) | −0.0047 (13) | 0.0126 (13) | −0.0402 (18) |
C22 | 0.0538 (14) | 0.117 (3) | 0.0624 (15) | −0.0143 (15) | 0.0130 (11) | 0.0053 (16) |
C23 | 0.0511 (13) | 0.0758 (17) | 0.098 (2) | −0.0219 (12) | 0.0153 (13) | −0.0169 (16) |
C24 | 0.0338 (11) | 0.154 (3) | 0.0622 (15) | −0.0081 (15) | −0.0020 (10) | −0.0121 (18) |
C25 | 0.0369 (12) | 0.084 (2) | 0.160 (4) | 0.0166 (13) | 0.0215 (17) | 0.032 (2) |
C31 | 0.0407 (10) | 0.0503 (11) | 0.0453 (10) | 0.0006 (8) | 0.0039 (8) | −0.0067 (8) |
C32 | 0.0557 (12) | 0.0498 (12) | 0.0688 (14) | 0.0031 (10) | 0.0131 (10) | −0.0067 (10) |
C33 | 0.0628 (14) | 0.0638 (15) | 0.0800 (16) | 0.0185 (12) | 0.0178 (12) | −0.0093 (13) |
C34 | 0.0468 (12) | 0.0842 (17) | 0.0669 (15) | 0.0100 (12) | 0.0164 (11) | −0.0063 (13) |
C35 | 0.0464 (11) | 0.0691 (14) | 0.0552 (12) | −0.0054 (10) | 0.0106 (9) | 0.0015 (11) |
C36 | 0.0471 (11) | 0.0508 (11) | 0.0539 (11) | 0.0004 (9) | 0.0074 (9) | −0.0003 (9) |
Fe1—C11 | 2.0543 (18) | C21—C25 | 1.398 (5) |
Fe1—C12 | 2.0419 (19) | C22—C23 | 1.375 (4) |
Fe1—C13 | 2.038 (2) | C23—C24 | 1.390 (4) |
Fe1—C14 | 2.034 (2) | C24—C25 | 1.434 (5) |
Fe1—C15 | 2.040 (2) | C31—C32 | 1.385 (3) |
Fe1—C21 | 2.031 (3) | C31—C36 | 1.384 (3) |
Fe1—C22 | 2.034 (3) | C32—C33 | 1.384 (3) |
Fe1—C23 | 2.032 (2) | C33—C34 | 1.378 (4) |
Fe1—C24 | 2.026 (2) | C34—C35 | 1.374 (4) |
Fe1—C25 | 2.020 (3) | C35—C36 | 1.383 (3) |
Cl1—C35 | 1.742 (2) | C2—H2A | 0.9700 |
N1—C1 | 1.310 (3) | C2—H2B | 0.9700 |
N1—C4 | 1.389 (3) | C5—H5 | 0.9300 |
N2—C1 | 1.378 (3) | C6—H6 | 0.9300 |
N2—C2 | 1.456 (2) | C7—H7 | 0.9300 |
N2—C3 | 1.386 (2) | C8—H8 | 0.9300 |
C1—C31 | 1.480 (3) | C12—H12 | 0.9300 |
C2—C11 | 1.504 (3) | C13—H13 | 0.9300 |
C3—C4 | 1.395 (3) | C14—H14 | 0.9300 |
C3—C8 | 1.390 (3) | C15—H15 | 0.9300 |
C4—C5 | 1.396 (3) | C21—H21 | 0.9300 |
C5—C6 | 1.365 (4) | C22—H22 | 0.9300 |
C6—C7 | 1.394 (4) | C23—H23 | 0.9300 |
C7—C8 | 1.387 (4) | C24—H24 | 0.9300 |
C11—C12 | 1.420 (3) | C25—H25 | 0.9300 |
C11—C15 | 1.428 (3) | C32—H32 | 0.9300 |
C12—C13 | 1.422 (3) | C33—H33 | 0.9300 |
C13—C14 | 1.405 (3) | C34—H34 | 0.9300 |
C14—C15 | 1.419 (3) | C36—H36 | 0.9300 |
C21—C22 | 1.354 (5) | ||
C11—Fe1—C12 | 40.58 (8) | C22—C23—Fe1 | 70.31 (14) |
C11—Fe1—C13 | 68.61 (8) | C24—C23—Fe1 | 69.74 (15) |
C11—Fe1—C14 | 68.64 (9) | C23—C24—Fe1 | 70.19 (14) |
C11—Fe1—C15 | 40.83 (8) | C25—C24—Fe1 | 69.04 (14) |
C11—Fe1—C21 | 108.43 (10) | C21—C25—Fe1 | 70.20 (15) |
C11—Fe1—C22 | 123.82 (10) | C24—C25—Fe1 | 69.46 (15) |
C11—Fe1—C23 | 159.10 (11) | C32—C31—C1 | 122.05 (19) |
C11—Fe1—C24 | 159.29 (13) | C36—C31—C1 | 118.23 (18) |
C11—Fe1—C25 | 122.67 (12) | C32—C31—C36 | 119.69 (19) |
C1—N1—C4 | 104.77 (17) | C31—C32—C33 | 119.8 (2) |
C1—N2—C2 | 128.44 (16) | C32—C33—C34 | 120.9 (2) |
C1—N2—C3 | 105.85 (16) | C33—C34—C35 | 118.7 (2) |
C2—N2—C3 | 124.26 (17) | C34—C35—C36 | 121.6 (2) |
N1—C1—N2 | 113.52 (17) | C34—C35—Cl1 | 119.60 (18) |
N1—C1—C31 | 123.68 (19) | C36—C35—Cl1 | 118.82 (19) |
N2—C1—C31 | 122.80 (18) | C31—C36—C35 | 119.3 (2) |
N2—C2—C11 | 111.86 (15) | N2—C2—H2A | 109.2 |
N2—C3—C4 | 105.63 (17) | N2—C2—H2B | 109.2 |
N2—C3—C8 | 131.8 (2) | C11—C2—H2A | 109.2 |
C4—C3—C8 | 122.6 (2) | C11—C2—H2B | 109.2 |
N1—C4—C3 | 110.20 (17) | C4—C5—H5 | 120.9 |
N1—C4—C5 | 130.1 (2) | C6—C5—H5 | 120.9 |
C3—C4—C5 | 119.7 (2) | C5—C6—H6 | 119.2 |
C4—C5—C6 | 118.2 (3) | C7—C6—H6 | 119.2 |
C5—C6—C7 | 121.6 (2) | C6—C7—H7 | 119.2 |
C6—C7—C8 | 121.6 (2) | C8—C7—H7 | 119.2 |
C3—C8—C7 | 116.3 (3) | C3—C8—H8 | 121.9 |
C12—C11—C2 | 126.85 (18) | C7—C8—H8 | 121.9 |
C15—C11—C2 | 126.04 (18) | C11—C12—H12 | 125.8 |
C12—C11—C15 | 107.08 (18) | C13—C12—H12 | 125.8 |
C11—C12—C13 | 108.48 (19) | C12—C13—H13 | 126.0 |
C12—C13—C14 | 107.95 (19) | C14—C13—H13 | 126.0 |
C13—C14—C15 | 108.4 (2) | C13—C14—H14 | 125.8 |
C11—C15—C14 | 108.09 (19) | C15—C14—H14 | 125.8 |
C2—C11—Fe1 | 128.43 (13) | C11—C15—H15 | 126.0 |
C12—C11—Fe1 | 69.24 (11) | C14—C15—H15 | 126.0 |
C15—C11—Fe1 | 69.05 (11) | C22—C21—H21 | 125.7 |
C11—C12—Fe1 | 70.18 (11) | C25—C21—H21 | 125.7 |
C13—C12—Fe1 | 69.46 (12) | C21—C22—H22 | 125.3 |
C12—C13—Fe1 | 69.76 (12) | C23—C22—H22 | 125.3 |
C14—C13—Fe1 | 69.66 (12) | C22—C23—H23 | 125.5 |
C13—C14—Fe1 | 69.97 (13) | C24—C23—H23 | 125.5 |
C15—C14—Fe1 | 69.85 (12) | C23—C24—H24 | 127.0 |
C11—C15—Fe1 | 70.12 (11) | C25—C24—H24 | 127.0 |
C14—C15—Fe1 | 69.37 (13) | C21—C25—H25 | 126.5 |
C22—C21—C25 | 108.6 (3) | C24—C25—H25 | 126.5 |
C21—C22—C23 | 109.4 (3) | C31—C32—H32 | 120.1 |
C22—C23—C24 | 109.0 (3) | C33—C32—H32 | 120.1 |
C23—C24—C25 | 106.0 (3) | C32—C33—H33 | 119.5 |
C21—C25—C24 | 107.0 (3) | C34—C33—H33 | 119.5 |
C22—C21—Fe1 | 70.68 (16) | C33—C34—H34 | 120.7 |
C25—C21—Fe1 | 69.42 (16) | C35—C34—H34 | 120.7 |
C21—C22—Fe1 | 70.41 (17) | C31—C36—H36 | 120.3 |
C23—C22—Fe1 | 70.16 (15) | C35—C36—H36 | 120.3 |
C4—N1—C1—N2 | 0.8 (2) | N2—C2—C11—Fe1 | 110.27 (17) |
C4—N1—C1—C31 | −179.03 (17) | C12—Fe1—C11—C2 | −121.2 (2) |
C3—N2—C1—N1 | 0.2 (2) | C13—Fe1—C11—C2 | −158.8 (2) |
C2—N2—C1—N1 | 166.77 (17) | C14—Fe1—C11—C2 | 157.7 (2) |
C3—N2—C1—C31 | 180.00 (16) | C15—Fe1—C11—C2 | 120.0 (2) |
C2—N2—C1—C31 | −13.4 (3) | C21—Fe1—C11—C2 | −2.8 (2) |
C1—N2—C2—C11 | −92.6 (2) | C22—Fe1—C11—C2 | −43.0 (2) |
C3—N2—C2—C11 | 71.7 (2) | C23—Fe1—C11—C2 | −75.0 (3) |
C1—N2—C3—C8 | 179.3 (2) | C24—Fe1—C11—C2 | 74.5 (3) |
C2—N2—C3—C8 | 12.0 (3) | C25—Fe1—C11—C2 | 39.5 (2) |
C1—N2—C3—C4 | −1.1 (2) | C15—C11—C12—C13 | 0.2 (2) |
C2—N2—C3—C4 | −168.37 (16) | C2—C11—C12—C13 | −177.78 (18) |
C1—N1—C4—C3 | −1.5 (2) | N1—C1—C31—C36 | −51.4 (3) |
C1—N1—C4—C5 | 179.5 (2) | N2—C1—C31—C36 | 128.8 (2) |
N2—C3—C4—N1 | 1.6 (2) | N1—C1—C31—C32 | 126.9 (2) |
C8—C3—C4—N1 | −178.74 (18) | N2—C1—C31—C32 | −52.9 (3) |
N2—C3—C4—C5 | −179.24 (18) | C36—C31—C32—C33 | −0.7 (4) |
C8—C3—C4—C5 | 0.4 (3) | C1—C31—C32—C33 | −179.0 (2) |
N1—C4—C5—C6 | 179.6 (2) | C31—C32—C33—C34 | 0.0 (4) |
C3—C4—C5—C6 | 0.6 (3) | C32—C33—C34—C35 | −0.1 (4) |
C4—C5—C6—C7 | −0.4 (4) | C33—C34—C35—C36 | 1.1 (4) |
C5—C6—C7—C8 | −0.8 (4) | C33—C34—C35—Cl1 | −177.7 (2) |
C6—C7—C8—C3 | 1.8 (4) | C34—C35—C36—C31 | −1.8 (4) |
N2—C3—C8—C7 | 178.0 (2) | Cl1—C35—C36—C31 | 177.04 (17) |
C4—C3—C8—C7 | −1.6 (3) | C32—C31—C36—C35 | 1.5 (3) |
N2—C2—C11—C12 | 18.6 (3) | C1—C31—C36—C35 | 180.0 (2) |
N2—C2—C11—C15 | −158.99 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
C25—H25···Cl1i | 0.93 | 3.05 | 3.802 (5) | 139 |
C36—H36···Cl1ii | 0.93 | 3.03 | 3.670 (2) | 127 |
Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) −x+2, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [Fe(C5H5)(C19H14ClN2)] |
Mr | 426.71 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 297 |
a, b, c (Å) | 11.6838 (9), 9.9220 (6), 16.7493 (14) |
β (°) | 90.542 (6) |
V (Å3) | 1941.6 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.93 |
Crystal size (mm) | 0.37 × 0.24 × 0.21 |
Data collection | |
Diffractometer | Bruker P4 diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.682, 0.746 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5483, 4669, 3646 |
Rint | 0.033 |
(sin θ/λ)max (Å−1) | 0.661 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.105, 1.03 |
No. of reflections | 4669 |
No. of parameters | 253 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.70, −0.55 |
Computer programs: XSCANS (Siemens, 1994), XSCANS, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996) and PLATON (Spek, 1998), SHELXL97 and PREP8 (Ferguson, 1998).
Fe1—C11 | 2.0543 (18) | Fe1—C25 | 2.020 (3) |
Fe1—C12 | 2.0419 (19) | Cl1—C35 | 1.742 (2) |
Fe1—C13 | 2.038 (2) | N1—C1 | 1.310 (3) |
Fe1—C14 | 2.034 (2) | N1—C4 | 1.389 (3) |
Fe1—C15 | 2.040 (2) | N2—C1 | 1.378 (3) |
Fe1—C21 | 2.031 (3) | N2—C2 | 1.456 (2) |
Fe1—C22 | 2.034 (3) | N2—C3 | 1.386 (2) |
Fe1—C23 | 2.032 (2) | C1—C31 | 1.480 (3) |
Fe1—C24 | 2.026 (2) | C2—C11 | 1.504 (3) |
C1—N1—C4 | 104.77 (17) | N1—C1—C31 | 123.68 (19) |
C1—N2—C2 | 128.44 (16) | N2—C1—C31 | 122.80 (18) |
C1—N2—C3 | 105.85 (16) | N2—C2—C11 | 111.86 (15) |
C2—N2—C3 | 124.26 (17) | C2—C11—Fe1 | 128.43 (13) |
N1—C1—N2 | 113.52 (17) | ||
C3—N2—C2—C11 | 71.7 (2) | C21—Fe1—C11—C2 | −2.8 (2) |
N2—C2—C11—C12 | 18.6 (3) | N2—C1—C31—C36 | 128.8 (2) |
N2—C2—C11—Fe1 | 110.27 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
C25—H25···Cl1i | 0.93 | 3.05 | 3.802 (5) | 139 |
C36—H36···Cl1ii | 0.93 | 3.03 | 3.670 (2) | 127 |
Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) −x+2, −y, −z+1. |
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The synthesis of anion receptors is currently an area of intense research activity due primarily to the ubiquitous roles which anions play in both chemical and biological processes, for example, as substrates or co-factors for enzymes and as nucleophiles, redox agents and phase transfer catalysts. In the past decade, combinations of an organometallic moiety with an amide N—H group have been demonstrated to be essential components in many anion-recognition receptors (Beer, 1998; Kingston et al., 1999). 1,3-Disubstituted imidazolium cations have been utilized as such recently (Sato et al., 1999; Thomas et al., 2000) and their synthetic intermediates (imidazolin-2-ylidenes) are also of interest as carbenes and the subject of several synthetic and structural investigations (Benito et al., 1995; Bildstein et al., 1998, 1999).
Recently, benzimidazole systems have attracted our considerable attention in synthetic and applied biological research (Howarth et al., 2000; Thomas et al., 2000; Howarth & Hanlon, 2001). Compound (I), depicted in Fig. 1, is obtained from 2-(3-chlorophenyl)benzimidazole and (trimethyl)ammoniumferrocenylmethyl iodide (Pauson et al., 1966; Ferguson et al., 1994a) and is an important electroactive model compound for application in anion sensor studies (Thomas et al., 2000), as well as in malarial parasite research (Howarth & Hanlon, 2001).
In (I), selected bond lengths and angles are listed in Table 1. The Fe—C bond lengths are in the range 2.020 (3)–2.0543 (18) Å; the Fe1···Cg(1,2) distances (Cg1 and Cg2 are centroids of the cyclopentadienyl rings) are comparable, 1.6467 (10) and 1.6487 (11) Å for the substituted and unsubstituted rings, respectively, with a linear Cg1···Fe1···Cg2 angle of 179.12 (7)°. The cyclopentadienyl rings are essentially eclipsed, with a C21—Fe1—C11—C2 torsion angle of -2.8 (2)° and there is no evidence for disorder in the unsubstituted C5H5 ring. The Fe—CCp—Csp3 angle is 128.43 (13)° and similar to 128.3 (3)° in N-ferrocenylmethyl-2-ferrocenylbenzimidazole, (II) (Benito et al., 1995), or 127.86 (12) and 126.80 (12)° in the two independent molecules of racemic ferrocenyl(phenyl)methanol (Ferguson et al., 1994b). The benzimidazole is twisted with respect to the ferrocenyl moiety, with Fe1—-CCp–Csp3—N2 = 110.27 (17)° and CCp—Csp3—N2—C3 = 71.7 (2)° [the N1—C1—C31—C32 angle is 126.9 (2)°], and due to the bulky ferrocenyl and benzimidazole groups avoiding possible sterically hindered H···H contacts. In the crystal structure, the shortest H···Cl1 contacts and involving C25—H25 and C36—H36 [C···Cl 3.802 (5) and 3.670 (2) Å] are listed in Table 2.
A search of the October 2000 version of the Cambridge Structural Database using CONQUEST Version 1.1 (Allen & Kennard, 1993) for molecules similar to (I) shows that such compounds are relatively rare and include N-ferrocenylmethyl-2-ferrocenylbenzimidazole (ZIJPIR; Benito et al., 1995) and N-ferrocenylmethyl-2-ferrocenyl-benzimidazolium tetrafluoroborate (GIFLUC; Li et al., 1998), which differ from (I) primarily through replacement of the chlorophenyl group by a ferrocenyl group.