Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805038730/rn6073sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805038730/rn6073Isup2.hkl |
CCDC reference: 296633
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.005 Å
- Disorder in main residue
- R factor = 0.042
- wR factor = 0.107
- Data-to-parameter ratio = 13.8
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for N1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Fe1 PLAT301_ALERT_3_C Main Residue Disorder ......................... 21.00 Perc. PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 29.80 Deg. C18 -C11 -C18' 1.555 1.555 1.555
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 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 3 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 1 ALERT type 4 Improvement, methodology, query or suggestion
[(4-Anilinylimino)2-chlorophenylmethyl]ferrocene (4.14 g, 0.010 mol) was dissolved in 100 ml of anhydrous acetonitrile and added dropwise over 40 min to a tert-butyl nitrite–copper(I1) chloride mixture in acetonitrile. The reaction procedure and work-up method were identical with those described in the previous syntheses. Following the removal of ether, the solid residue was crystallized from ethyl acetate and petroleum ether (333–363 K). A red solid product was obtained. Analysis calculated for C23H17Cl2FeN: C 63.63, H 3.95, N 3.23%; found: C 63.25, H 4.01, N 3.12%.
The benzene ring which has an ortho-chlorine substituent is disordered. It is thought as a regular hexagon when it is amended. [Please clarify] The probability of their appearance is 60.9 and 39.1%. All H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H = 0.93–0.98 Å and Uiso(H) = 1.2Ueq(C).
Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
[Fe(C5H5)(C18H12Cl2N)] | Dx = 1.492 Mg m−3 |
Mr = 434.13 | Melting point: 446 K |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 8.226 (3) Å | Cell parameters from 2747 reflections |
b = 17.288 (6) Å | θ = 2.8–23.1° |
c = 13.996 (5) Å | µ = 1.06 mm−1 |
β = 103.820 (6)° | T = 294 K |
V = 1932.8 (11) Å3 | Prism, red |
Z = 4 | 0.22 × 0.18 × 0.12 mm |
F(000) = 888 |
Bruker SMART CCD area-detector diffractometer | 3918 independent reflections |
Radiation source: fine-focus sealed tube | 2546 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
ϕ and ω scans | θmax = 26.4°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −7→10 |
Tmin = 0.720, Tmax = 0.880 | k = −21→21 |
10709 measured reflections | l = −17→16 |
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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.107 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0445P)2 + 0.4751P] where P = (Fo2 + 2Fc2)/3 |
3918 reflections | (Δ/σ)max = 0.001 |
284 parameters | Δρmax = 0.29 e Å−3 |
8 restraints | Δρmin = −0.26 e Å−3 |
[Fe(C5H5)(C18H12Cl2N)] | V = 1932.8 (11) Å3 |
Mr = 434.13 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 8.226 (3) Å | µ = 1.06 mm−1 |
b = 17.288 (6) Å | T = 294 K |
c = 13.996 (5) Å | 0.22 × 0.18 × 0.12 mm |
β = 103.820 (6)° |
Bruker SMART CCD area-detector diffractometer | 3918 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2546 reflections with I > 2σ(I) |
Tmin = 0.720, Tmax = 0.880 | Rint = 0.037 |
10709 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | 8 restraints |
wR(F2) = 0.107 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.29 e Å−3 |
3918 reflections | Δρmin = −0.26 e Å−3 |
284 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) | |
Fe1 | 0.04210 (5) | 1.15546 (2) | 0.80381 (3) | 0.04694 (15) | |
Cl1 | 0.20257 (12) | 0.61035 (5) | 0.96107 (7) | 0.0748 (3) | |
N1 | 0.1753 (4) | 0.95056 (15) | 0.9168 (2) | 0.0706 (8) | |
C1 | −0.0892 (4) | 1.1548 (2) | 0.6610 (3) | 0.0729 (11) | |
H1A | −0.0447 | 1.1423 | 0.6039 | 0.087* | |
C2 | −0.1608 (4) | 1.1020 (2) | 0.7159 (3) | 0.0703 (10) | |
H2A | −0.1733 | 1.0462 | 0.7040 | 0.084* | |
C3 | −0.2093 (4) | 1.1428 (2) | 0.7915 (3) | 0.0711 (10) | |
H3A | −0.2625 | 1.1210 | 0.8411 | 0.085* | |
C4 | −0.1676 (4) | 1.2211 (2) | 0.7821 (3) | 0.0674 (9) | |
H4A | −0.1866 | 1.2633 | 0.8249 | 0.081* | |
C5 | −0.0951 (4) | 1.2289 (2) | 0.7023 (3) | 0.0705 (10) | |
H5A | −0.0553 | 1.2771 | 0.6791 | 0.085* | |
C6 | 0.2883 (4) | 1.13291 (17) | 0.8111 (2) | 0.0528 (8) | |
H6A | 0.3367 | 1.1215 | 0.7551 | 0.063* | |
C7 | 0.2689 (4) | 1.20758 (18) | 0.8491 (3) | 0.0620 (9) | |
H7A | 0.3025 | 1.2566 | 0.8244 | 0.074* | |
C8 | 0.1939 (4) | 1.19857 (19) | 0.9295 (3) | 0.0663 (10) | |
H8A | 0.1652 | 1.2407 | 0.9694 | 0.080* | |
C9 | 0.1627 (4) | 1.11882 (18) | 0.9411 (2) | 0.0580 (8) | |
H9A | 0.1101 | 1.0962 | 0.9905 | 0.070* | |
C10 | 0.2231 (4) | 1.07724 (16) | 0.8678 (2) | 0.0469 (7) | |
C11 | 0.2273 (3) | 0.99278 (16) | 0.8571 (2) | 0.0466 (7) | |
C12 | 0.1885 (4) | 0.86908 (17) | 0.9181 (2) | 0.0535 (8) | |
C13 | 0.0524 (4) | 0.8229 (2) | 0.8733 (3) | 0.0650 (9) | |
H13A | −0.0433 | 0.8457 | 0.8346 | 0.078* | |
C14 | 0.0583 (4) | 0.74411 (19) | 0.8857 (3) | 0.0621 (9) | |
H14A | −0.0327 | 0.7138 | 0.8552 | 0.075* | |
C15 | 0.1983 (4) | 0.71032 (16) | 0.9430 (2) | 0.0495 (7) | |
C16 | 0.3343 (4) | 0.75422 (18) | 0.9866 (2) | 0.0549 (8) | |
H16A | 0.4297 | 0.7308 | 1.0247 | 0.066* | |
C17 | 0.3288 (4) | 0.83326 (18) | 0.9737 (2) | 0.0573 (8) | |
H17A | 0.4216 | 0.8629 | 1.0031 | 0.069* | |
Cl2 | 0.5914 (3) | 0.96401 (14) | 0.86150 (15) | 0.0764 (7) | 0.609 (3) |
C18 | 0.2665 (5) | 0.9622 (2) | 0.7640 (2) | 0.0442 (14) | 0.609 (3) |
C19 | 0.1374 (4) | 0.9503 (3) | 0.6809 (3) | 0.062 (2) | 0.609 (3) |
H19A | 0.0270 | 0.9587 | 0.6837 | 0.075* | 0.609 (3) |
C20 | 0.1734 (6) | 0.9259 (2) | 0.5936 (2) | 0.0709 (19) | 0.609 (3) |
H20A | 0.0871 | 0.9180 | 0.5380 | 0.085* | 0.609 (3) |
C21 | 0.3385 (7) | 0.9133 (2) | 0.5894 (3) | 0.0645 (16) | 0.609 (3) |
H21A | 0.3626 | 0.8970 | 0.5310 | 0.077* | 0.609 (3) |
C22 | 0.4675 (5) | 0.9252 (3) | 0.6725 (4) | 0.062 (2) | 0.609 (3) |
H22A | 0.5780 | 0.9168 | 0.6697 | 0.074* | 0.609 (3) |
C23 | 0.4315 (4) | 0.9496 (2) | 0.7598 (3) | 0.0521 (14) | 0.609 (3) |
Cl2' | 0.0965 (4) | 0.92729 (19) | 0.6488 (2) | 0.0791 (12) | 0.391 (3) |
C18' | 0.3528 (6) | 0.9637 (4) | 0.8018 (4) | 0.044 (2) | 0.391 (3) |
C19' | 0.5219 (8) | 0.9710 (4) | 0.8472 (4) | 0.049 (3) | 0.391 (3) |
H19B | 0.5547 | 0.9897 | 0.9112 | 0.059* | 0.391 (3) |
C20' | 0.6421 (6) | 0.9504 (4) | 0.7968 (6) | 0.067 (3) | 0.391 (3) |
H20B | 0.7552 | 0.9553 | 0.8272 | 0.080* | 0.391 (3) |
C21' | 0.5931 (9) | 0.9225 (4) | 0.7011 (6) | 0.074 (3) | 0.391 (3) |
H21B | 0.6735 | 0.9087 | 0.6675 | 0.089* | 0.391 (3) |
C22' | 0.4240 (11) | 0.9152 (4) | 0.6557 (4) | 0.062 (4) | 0.391 (3) |
H22B | 0.3912 | 0.8965 | 0.5917 | 0.075* | 0.391 (3) |
C23' | 0.3039 (7) | 0.9358 (4) | 0.7061 (4) | 0.058 (2) | 0.391 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe1 | 0.0467 (3) | 0.0469 (3) | 0.0449 (3) | 0.00305 (19) | 0.00632 (18) | −0.0010 (2) |
Cl1 | 0.0898 (7) | 0.0514 (5) | 0.0868 (7) | −0.0089 (4) | 0.0281 (5) | 0.0046 (4) |
N1 | 0.102 (2) | 0.0446 (16) | 0.080 (2) | 0.0120 (15) | 0.0497 (19) | −0.0019 (15) |
C1 | 0.057 (2) | 0.112 (3) | 0.0446 (19) | −0.001 (2) | 0.0008 (16) | −0.001 (2) |
C2 | 0.056 (2) | 0.069 (2) | 0.078 (3) | −0.0095 (18) | −0.0011 (19) | −0.009 (2) |
C3 | 0.053 (2) | 0.080 (3) | 0.082 (3) | 0.0008 (18) | 0.0199 (18) | 0.012 (2) |
C4 | 0.055 (2) | 0.070 (2) | 0.074 (3) | 0.0139 (18) | 0.0089 (18) | 0.0047 (19) |
C5 | 0.064 (2) | 0.068 (2) | 0.069 (3) | 0.0063 (18) | −0.0034 (19) | 0.021 (2) |
C6 | 0.0434 (17) | 0.0512 (18) | 0.059 (2) | 0.0020 (14) | 0.0039 (15) | −0.0040 (15) |
C7 | 0.055 (2) | 0.0481 (19) | 0.074 (2) | −0.0031 (15) | −0.0022 (18) | −0.0057 (16) |
C8 | 0.079 (2) | 0.051 (2) | 0.057 (2) | 0.0130 (17) | −0.0074 (18) | −0.0149 (16) |
C9 | 0.075 (2) | 0.0521 (19) | 0.0418 (18) | 0.0166 (16) | 0.0047 (16) | −0.0026 (14) |
C10 | 0.0479 (17) | 0.0475 (17) | 0.0415 (17) | 0.0080 (14) | 0.0031 (13) | −0.0044 (13) |
C11 | 0.0468 (17) | 0.0475 (17) | 0.0430 (17) | 0.0061 (14) | 0.0056 (14) | −0.0018 (14) |
C12 | 0.066 (2) | 0.0490 (18) | 0.0523 (19) | 0.0068 (16) | 0.0279 (17) | 0.0021 (14) |
C13 | 0.059 (2) | 0.067 (2) | 0.065 (2) | 0.0141 (18) | 0.0063 (17) | 0.0024 (18) |
C14 | 0.051 (2) | 0.062 (2) | 0.070 (2) | −0.0045 (16) | 0.0075 (17) | −0.0088 (17) |
C15 | 0.0519 (19) | 0.0455 (17) | 0.0541 (19) | −0.0040 (14) | 0.0188 (15) | −0.0013 (14) |
C16 | 0.0509 (19) | 0.055 (2) | 0.057 (2) | 0.0047 (15) | 0.0093 (15) | −0.0009 (15) |
C17 | 0.0530 (19) | 0.052 (2) | 0.068 (2) | −0.0063 (15) | 0.0167 (16) | −0.0105 (16) |
Cl2 | 0.0525 (13) | 0.1004 (14) | 0.0704 (12) | 0.0020 (9) | 0.0029 (9) | 0.0074 (10) |
C18 | 0.049 (4) | 0.038 (3) | 0.042 (4) | 0.006 (3) | 0.006 (3) | −0.002 (3) |
C19 | 0.076 (6) | 0.061 (4) | 0.050 (5) | −0.007 (3) | 0.017 (4) | −0.025 (3) |
C20 | 0.100 (6) | 0.063 (4) | 0.042 (4) | −0.004 (3) | 0.001 (3) | −0.021 (3) |
C21 | 0.095 (5) | 0.046 (3) | 0.059 (4) | −0.001 (3) | 0.030 (4) | −0.013 (3) |
C22 | 0.078 (6) | 0.047 (5) | 0.069 (5) | 0.008 (4) | 0.035 (5) | 0.003 (4) |
C23 | 0.056 (4) | 0.048 (3) | 0.054 (4) | 0.009 (3) | 0.016 (3) | 0.003 (3) |
Cl2' | 0.093 (2) | 0.077 (2) | 0.056 (2) | −0.0017 (16) | −0.0051 (16) | −0.0216 (16) |
C18' | 0.045 (6) | 0.041 (4) | 0.046 (6) | 0.005 (4) | 0.007 (4) | −0.003 (4) |
C19' | 0.052 (5) | 0.048 (4) | 0.051 (5) | 0.002 (4) | 0.018 (4) | −0.001 (3) |
C20' | 0.058 (6) | 0.059 (6) | 0.092 (8) | 0.008 (4) | 0.033 (6) | 0.016 (5) |
C21' | 0.100 (8) | 0.053 (6) | 0.091 (9) | 0.010 (6) | 0.064 (7) | 0.005 (5) |
C22' | 0.091 (8) | 0.046 (7) | 0.050 (8) | 0.000 (6) | 0.017 (7) | −0.006 (6) |
C23' | 0.077 (7) | 0.036 (4) | 0.064 (6) | 0.002 (4) | 0.026 (6) | −0.004 (4) |
Fe1—C4 | 2.026 (3) | C11—C18' | 1.517 (5) |
Fe1—C1 | 2.032 (3) | C12—C17 | 1.376 (4) |
Fe1—C7 | 2.032 (3) | C12—C13 | 1.396 (4) |
Fe1—C5 | 2.033 (3) | C13—C14 | 1.372 (4) |
Fe1—C8 | 2.040 (3) | C13—H13A | 0.9300 |
Fe1—C6 | 2.041 (3) | C14—C15 | 1.367 (4) |
Fe1—C9 | 2.041 (3) | C14—H14A | 0.9300 |
Fe1—C2 | 2.043 (3) | C15—C16 | 1.369 (4) |
Fe1—C3 | 2.045 (3) | C16—C17 | 1.378 (4) |
Fe1—C10 | 2.052 (3) | C16—H16A | 0.9300 |
Cl1—C15 | 1.746 (3) | C17—H17A | 0.9300 |
N1—C11 | 1.259 (4) | Cl2—C23 | 1.710 (4) |
N1—C12 | 1.413 (4) | C18—C19 | 1.3900 |
C1—C2 | 1.409 (5) | C18—C23 | 1.3900 |
C1—C5 | 1.411 (5) | C19—C20 | 1.3900 |
C1—H1A | 0.9800 | C19—H19A | 0.9300 |
C2—C3 | 1.406 (5) | C20—C21 | 1.3900 |
C2—H2A | 0.9800 | C20—H20A | 0.9300 |
C3—C4 | 1.410 (5) | C21—C22 | 1.3900 |
C3—H3A | 0.9800 | C21—H21A | 0.9300 |
C4—C5 | 1.392 (5) | C22—C23 | 1.3900 |
C4—H4A | 0.9800 | C22—H22A | 0.9300 |
C5—H5A | 0.9800 | Cl2'—C23' | 1.709 (6) |
C6—C7 | 1.419 (4) | C18'—C19' | 1.3900 |
C6—C10 | 1.431 (4) | C18'—C23' | 1.3900 |
C6—H6A | 0.9800 | C19'—C20' | 1.3900 |
C7—C8 | 1.416 (5) | C19'—H19B | 0.9300 |
C7—H7A | 0.9800 | C20'—C21' | 1.3900 |
C8—C9 | 1.419 (4) | C20'—H20B | 0.9300 |
C8—H8A | 0.9800 | C21'—C22' | 1.3900 |
C9—C10 | 1.435 (4) | C21'—H21B | 0.9300 |
C9—H9A | 0.9800 | C22'—C23' | 1.3900 |
C10—C11 | 1.469 (4) | C22'—H22B | 0.9300 |
C11—C18 | 1.510 (4) | ||
C4—Fe1—C1 | 67.80 (15) | C8—C7—Fe1 | 69.94 (19) |
C4—Fe1—C7 | 118.93 (14) | C6—C7—Fe1 | 69.94 (17) |
C1—Fe1—C7 | 122.82 (16) | C8—C7—H7A | 126.1 |
C4—Fe1—C5 | 40.10 (14) | C6—C7—H7A | 126.1 |
C1—Fe1—C5 | 40.62 (14) | Fe1—C7—H7A | 126.1 |
C7—Fe1—C5 | 104.84 (15) | C7—C8—C9 | 108.8 (3) |
C4—Fe1—C8 | 104.39 (14) | C7—C8—Fe1 | 69.37 (18) |
C1—Fe1—C8 | 157.30 (16) | C9—C8—Fe1 | 69.70 (17) |
C7—Fe1—C8 | 40.70 (13) | C7—C8—H8A | 125.6 |
C5—Fe1—C8 | 119.84 (15) | C9—C8—H8A | 125.6 |
C4—Fe1—C6 | 156.00 (14) | Fe1—C8—H8A | 125.6 |
C1—Fe1—C6 | 109.64 (14) | C8—C9—C10 | 107.6 (3) |
C7—Fe1—C6 | 40.78 (12) | C8—C9—Fe1 | 69.61 (18) |
C5—Fe1—C6 | 122.19 (15) | C10—C9—Fe1 | 69.87 (17) |
C8—Fe1—C6 | 68.34 (14) | C8—C9—H9A | 126.2 |
C4—Fe1—C9 | 121.33 (14) | C10—C9—H9A | 126.2 |
C1—Fe1—C9 | 161.54 (15) | Fe1—C9—H9A | 126.2 |
C7—Fe1—C9 | 68.94 (14) | C6—C10—C9 | 107.4 (3) |
C5—Fe1—C9 | 156.19 (14) | C6—C10—C11 | 126.2 (3) |
C8—Fe1—C9 | 40.69 (13) | C9—C10—C11 | 126.3 (3) |
C6—Fe1—C9 | 68.92 (13) | C6—C10—Fe1 | 69.14 (16) |
C4—Fe1—C2 | 67.62 (15) | C9—C10—Fe1 | 69.07 (16) |
C1—Fe1—C2 | 40.47 (14) | C11—C10—Fe1 | 130.0 (2) |
C7—Fe1—C2 | 161.04 (16) | N1—C11—C10 | 119.2 (3) |
C5—Fe1—C2 | 67.95 (15) | N1—C11—C18 | 123.1 (3) |
C8—Fe1—C2 | 158.20 (17) | C10—C11—C18 | 116.8 (3) |
C6—Fe1—C2 | 127.02 (14) | N1—C11—C18' | 121.8 (3) |
C9—Fe1—C2 | 124.73 (15) | C10—C11—C18' | 114.6 (3) |
C4—Fe1—C3 | 40.53 (13) | C18—C11—C18' | 29.8 (2) |
C1—Fe1—C3 | 68.13 (15) | C17—C12—C13 | 118.1 (3) |
C7—Fe1—C3 | 155.25 (15) | C17—C12—N1 | 120.5 (3) |
C5—Fe1—C3 | 68.08 (15) | C13—C12—N1 | 120.9 (3) |
C8—Fe1—C3 | 120.65 (16) | C14—C13—C12 | 120.7 (3) |
C6—Fe1—C3 | 162.75 (14) | C14—C13—H13A | 119.6 |
C9—Fe1—C3 | 107.46 (15) | C12—C13—H13A | 119.6 |
C2—Fe1—C3 | 40.24 (14) | C15—C14—C13 | 119.8 (3) |
C4—Fe1—C10 | 159.66 (14) | C15—C14—H14A | 120.1 |
C1—Fe1—C10 | 125.81 (14) | C13—C14—H14A | 120.1 |
C7—Fe1—C10 | 68.88 (12) | C14—C15—C16 | 120.6 (3) |
C5—Fe1—C10 | 160.02 (15) | C14—C15—Cl1 | 119.5 (2) |
C8—Fe1—C10 | 68.50 (12) | C16—C15—Cl1 | 119.9 (2) |
C6—Fe1—C10 | 40.92 (12) | C15—C16—C17 | 119.6 (3) |
C9—Fe1—C10 | 41.06 (11) | C15—C16—H16A | 120.2 |
C2—Fe1—C10 | 111.58 (13) | C17—C16—H16A | 120.2 |
C3—Fe1—C10 | 125.44 (13) | C12—C17—C16 | 121.1 (3) |
C11—N1—C12 | 123.3 (3) | C12—C17—H17A | 119.4 |
C2—C1—C5 | 107.7 (3) | C16—C17—H17A | 119.4 |
C2—C1—Fe1 | 70.2 (2) | C19—C18—C23 | 120.0 |
C5—C1—Fe1 | 69.74 (19) | C19—C18—C11 | 119.7 (3) |
C2—C1—H1A | 126.1 | C23—C18—C11 | 120.2 (3) |
C5—C1—H1A | 126.1 | C20—C19—C18 | 120.0 |
Fe1—C1—H1A | 126.1 | C20—C19—H19A | 120.0 |
C3—C2—C1 | 108.4 (3) | C18—C19—H19A | 120.0 |
C3—C2—Fe1 | 70.0 (2) | C19—C20—C21 | 120.0 |
C1—C2—Fe1 | 69.35 (19) | C19—C20—H20A | 120.0 |
C3—C2—H2A | 125.8 | C21—C20—H20A | 120.0 |
C1—C2—H2A | 125.8 | C22—C21—C20 | 120.0 |
Fe1—C2—H2A | 125.8 | C22—C21—H21A | 120.0 |
C2—C3—C4 | 107.0 (3) | C20—C21—H21A | 120.0 |
C2—C3—Fe1 | 69.78 (19) | C21—C22—C23 | 120.0 |
C4—C3—Fe1 | 69.02 (19) | C21—C22—H22A | 120.0 |
C2—C3—H3A | 126.5 | C23—C22—H22A | 120.0 |
C4—C3—H3A | 126.5 | C22—C23—C18 | 120.0 |
Fe1—C3—H3A | 126.5 | C22—C23—Cl2 | 119.5 (3) |
C5—C4—C3 | 109.1 (3) | C18—C23—Cl2 | 120.5 (3) |
C5—C4—Fe1 | 70.22 (19) | C19'—C18'—C23' | 120.0 |
C3—C4—Fe1 | 70.45 (19) | C19'—C18'—C11 | 117.8 (5) |
C5—C4—H4A | 125.4 | C23'—C18'—C11 | 122.1 (5) |
C3—C4—H4A | 125.4 | C18'—C19'—C20' | 120.0 |
Fe1—C4—H4A | 125.4 | C18'—C19'—H19B | 120.0 |
C4—C5—C1 | 107.7 (3) | C20'—C19'—H19B | 120.0 |
C4—C5—Fe1 | 69.69 (19) | C21'—C20'—C19' | 120.0 |
C1—C5—Fe1 | 69.64 (19) | C21'—C20'—H20B | 120.0 |
C4—C5—H5A | 126.1 | C19'—C20'—H20B | 120.0 |
C1—C5—H5A | 126.1 | C20'—C21'—C22' | 120.0 |
Fe1—C5—H5A | 126.1 | C20'—C21'—H21B | 120.0 |
C7—C6—C10 | 108.3 (3) | C22'—C21'—H21B | 120.0 |
C7—C6—Fe1 | 69.28 (17) | C23'—C22'—C21' | 120.0 |
C10—C6—Fe1 | 69.95 (17) | C23'—C22'—H22B | 120.0 |
C7—C6—H6A | 125.9 | C21'—C22'—H22B | 120.0 |
C10—C6—H6A | 125.9 | C22'—C23'—C18' | 120.0 |
Fe1—C6—H6A | 125.9 | C22'—C23'—Cl2' | 119.4 (5) |
C8—C7—C6 | 107.9 (3) | C18'—C23'—Cl2' | 120.6 (5) |
C4—Fe1—C1—C2 | −81.1 (2) | Fe1—C7—C8—C9 | 58.7 (2) |
C7—Fe1—C1—C2 | 167.9 (2) | C6—C7—C8—Fe1 | −59.9 (2) |
C5—Fe1—C1—C2 | −118.6 (3) | C4—Fe1—C8—C7 | −117.9 (2) |
C8—Fe1—C1—C2 | −154.8 (3) | C1—Fe1—C8—C7 | −51.3 (4) |
C6—Fe1—C1—C2 | 124.5 (2) | C5—Fe1—C8—C7 | −77.6 (2) |
C9—Fe1—C1—C2 | 42.4 (5) | C6—Fe1—C8—C7 | 38.03 (18) |
C3—Fe1—C1—C2 | −37.2 (2) | C9—Fe1—C8—C7 | 120.5 (3) |
C10—Fe1—C1—C2 | 81.6 (3) | C2—Fe1—C8—C7 | 176.8 (3) |
C4—Fe1—C1—C5 | 37.5 (2) | C3—Fe1—C8—C7 | −158.40 (19) |
C7—Fe1—C1—C5 | −73.5 (3) | C10—Fe1—C8—C7 | 82.2 (2) |
C8—Fe1—C1—C5 | −36.3 (5) | C4—Fe1—C8—C9 | 121.7 (2) |
C6—Fe1—C1—C5 | −116.9 (2) | C1—Fe1—C8—C9 | −171.7 (3) |
C9—Fe1—C1—C5 | 160.9 (4) | C7—Fe1—C8—C9 | −120.5 (3) |
C2—Fe1—C1—C5 | 118.6 (3) | C5—Fe1—C8—C9 | 161.9 (2) |
C3—Fe1—C1—C5 | 81.4 (2) | C6—Fe1—C8—C9 | −82.4 (2) |
C10—Fe1—C1—C5 | −159.9 (2) | C2—Fe1—C8—C9 | 56.3 (4) |
C5—C1—C2—C3 | −0.6 (4) | C3—Fe1—C8—C9 | 81.1 (2) |
Fe1—C1—C2—C3 | 59.3 (2) | C10—Fe1—C8—C9 | −38.28 (19) |
C5—C1—C2—Fe1 | −59.9 (2) | C7—C8—C9—C10 | 1.4 (4) |
C4—Fe1—C2—C3 | −38.2 (2) | Fe1—C8—C9—C10 | 59.8 (2) |
C1—Fe1—C2—C3 | −119.8 (3) | C7—C8—C9—Fe1 | −58.5 (2) |
C7—Fe1—C2—C3 | −152.5 (4) | C4—Fe1—C9—C8 | −74.8 (2) |
C5—Fe1—C2—C3 | −81.7 (2) | C1—Fe1—C9—C8 | 169.9 (4) |
C8—Fe1—C2—C3 | 34.0 (5) | C7—Fe1—C9—C8 | 37.0 (2) |
C6—Fe1—C2—C3 | 163.8 (2) | C5—Fe1—C9—C8 | −41.8 (4) |
C9—Fe1—C2—C3 | 75.3 (3) | C6—Fe1—C9—C8 | 80.9 (2) |
C10—Fe1—C2—C3 | 119.9 (2) | C2—Fe1—C9—C8 | −157.9 (2) |
C4—Fe1—C2—C1 | 81.6 (2) | C3—Fe1—C9—C8 | −117.0 (2) |
C7—Fe1—C2—C1 | −32.7 (5) | C10—Fe1—C9—C8 | 118.6 (3) |
C5—Fe1—C2—C1 | 38.1 (2) | C4—Fe1—C9—C10 | 166.51 (19) |
C8—Fe1—C2—C1 | 153.8 (3) | C1—Fe1—C9—C10 | 51.3 (5) |
C6—Fe1—C2—C1 | −76.4 (3) | C7—Fe1—C9—C10 | −81.6 (2) |
C9—Fe1—C2—C1 | −164.9 (2) | C5—Fe1—C9—C10 | −160.5 (3) |
C3—Fe1—C2—C1 | 119.8 (3) | C8—Fe1—C9—C10 | −118.6 (3) |
C10—Fe1—C2—C1 | −120.4 (2) | C6—Fe1—C9—C10 | −37.77 (18) |
C1—C2—C3—C4 | 0.3 (4) | C2—Fe1—C9—C10 | 83.4 (2) |
Fe1—C2—C3—C4 | 59.2 (2) | C3—Fe1—C9—C10 | 124.4 (2) |
C1—C2—C3—Fe1 | −58.9 (2) | C7—C6—C10—C9 | 0.2 (3) |
C4—Fe1—C3—C2 | 118.4 (3) | Fe1—C6—C10—C9 | −58.7 (2) |
C1—Fe1—C3—C2 | 37.4 (2) | C7—C6—C10—C11 | −176.2 (3) |
C7—Fe1—C3—C2 | 159.0 (3) | Fe1—C6—C10—C11 | 125.0 (3) |
C5—Fe1—C3—C2 | 81.3 (2) | C7—C6—C10—Fe1 | 58.8 (2) |
C8—Fe1—C3—C2 | −166.0 (2) | C8—C9—C10—C6 | −0.9 (3) |
C6—Fe1—C3—C2 | −48.5 (6) | Fe1—C9—C10—C6 | 58.7 (2) |
C9—Fe1—C3—C2 | −123.6 (2) | C8—C9—C10—C11 | 175.4 (3) |
C10—Fe1—C3—C2 | −81.8 (3) | Fe1—C9—C10—C11 | −125.0 (3) |
C1—Fe1—C3—C4 | −81.0 (2) | C8—C9—C10—Fe1 | −59.6 (2) |
C7—Fe1—C3—C4 | 40.6 (5) | C4—Fe1—C10—C6 | −154.2 (4) |
C5—Fe1—C3—C4 | −37.0 (2) | C1—Fe1—C10—C6 | 78.5 (2) |
C8—Fe1—C3—C4 | 75.6 (3) | C7—Fe1—C10—C6 | −37.47 (19) |
C6—Fe1—C3—C4 | −166.9 (4) | C5—Fe1—C10—C6 | 37.5 (5) |
C9—Fe1—C3—C4 | 118.1 (2) | C8—Fe1—C10—C6 | −81.3 (2) |
C2—Fe1—C3—C4 | −118.4 (3) | C9—Fe1—C10—C6 | −119.2 (3) |
C10—Fe1—C3—C4 | 159.8 (2) | C2—Fe1—C10—C6 | 122.2 (2) |
C2—C3—C4—C5 | 0.1 (4) | C3—Fe1—C10—C6 | 165.6 (2) |
Fe1—C3—C4—C5 | 59.8 (2) | C4—Fe1—C10—C9 | −35.0 (5) |
C2—C3—C4—Fe1 | −59.7 (2) | C1—Fe1—C10—C9 | −162.3 (2) |
C1—Fe1—C4—C5 | −38.0 (2) | C7—Fe1—C10—C9 | 81.8 (2) |
C7—Fe1—C4—C5 | 78.3 (3) | C5—Fe1—C10—C9 | 156.8 (4) |
C8—Fe1—C4—C5 | 119.5 (2) | C8—Fe1—C10—C9 | 37.9 (2) |
C6—Fe1—C4—C5 | 50.6 (4) | C6—Fe1—C10—C9 | 119.2 (3) |
C9—Fe1—C4—C5 | 160.0 (2) | C2—Fe1—C10—C9 | −118.6 (2) |
C2—Fe1—C4—C5 | −81.9 (2) | C3—Fe1—C10—C9 | −75.2 (2) |
C3—Fe1—C4—C5 | −119.8 (3) | C4—Fe1—C10—C11 | 85.4 (5) |
C10—Fe1—C4—C5 | −173.8 (3) | C1—Fe1—C10—C11 | −41.9 (3) |
C1—Fe1—C4—C3 | 81.8 (2) | C7—Fe1—C10—C11 | −157.9 (3) |
C7—Fe1—C4—C3 | −161.8 (2) | C5—Fe1—C10—C11 | −82.9 (5) |
C5—Fe1—C4—C3 | 119.8 (3) | C8—Fe1—C10—C11 | 158.3 (3) |
C8—Fe1—C4—C3 | −120.7 (2) | C6—Fe1—C10—C11 | −120.4 (3) |
C6—Fe1—C4—C3 | 170.5 (3) | C9—Fe1—C10—C11 | 120.4 (4) |
C9—Fe1—C4—C3 | −80.1 (3) | C2—Fe1—C10—C11 | 1.8 (3) |
C2—Fe1—C4—C3 | 37.9 (2) | C3—Fe1—C10—C11 | 45.2 (3) |
C10—Fe1—C4—C3 | −54.0 (5) | C12—N1—C11—C10 | −174.0 (3) |
C3—C4—C5—C1 | −0.5 (4) | C12—N1—C11—C18 | 16.9 (5) |
Fe1—C4—C5—C1 | 59.5 (2) | C12—N1—C11—C18' | −18.5 (6) |
C3—C4—C5—Fe1 | −59.9 (2) | C6—C10—C11—N1 | 175.1 (3) |
C2—C1—C5—C4 | 0.7 (4) | C9—C10—C11—N1 | −0.6 (5) |
Fe1—C1—C5—C4 | −59.5 (2) | Fe1—C10—C11—N1 | −92.7 (3) |
C2—C1—C5—Fe1 | 60.2 (2) | C6—C10—C11—C18 | −15.2 (4) |
C1—Fe1—C5—C4 | 118.9 (3) | C9—C10—C11—C18 | 169.2 (3) |
C7—Fe1—C5—C4 | −117.5 (2) | Fe1—C10—C11—C18 | 77.0 (4) |
C8—Fe1—C5—C4 | −76.3 (3) | C6—C10—C11—C18' | 17.9 (5) |
C6—Fe1—C5—C4 | −158.2 (2) | C9—C10—C11—C18' | −157.8 (4) |
C9—Fe1—C5—C4 | −46.2 (5) | Fe1—C10—C11—C18' | 110.1 (4) |
C2—Fe1—C5—C4 | 81.0 (2) | C11—N1—C12—C17 | 88.9 (4) |
C3—Fe1—C5—C4 | 37.4 (2) | C11—N1—C12—C13 | −99.2 (4) |
C10—Fe1—C5—C4 | 173.7 (3) | C17—C12—C13—C14 | 0.8 (5) |
C4—Fe1—C5—C1 | −118.9 (3) | N1—C12—C13—C14 | −171.3 (3) |
C7—Fe1—C5—C1 | 123.5 (2) | C12—C13—C14—C15 | 0.4 (5) |
C8—Fe1—C5—C1 | 164.7 (2) | C13—C14—C15—C16 | −1.3 (5) |
C6—Fe1—C5—C1 | 82.9 (2) | C13—C14—C15—Cl1 | 178.2 (3) |
C9—Fe1—C5—C1 | −165.2 (3) | C14—C15—C16—C17 | 0.9 (5) |
C2—Fe1—C5—C1 | −38.0 (2) | Cl1—C15—C16—C17 | −178.6 (2) |
C3—Fe1—C5—C1 | −81.5 (2) | C13—C12—C17—C16 | −1.2 (5) |
C10—Fe1—C5—C1 | 54.8 (5) | N1—C12—C17—C16 | 170.9 (3) |
C4—Fe1—C6—C7 | 38.5 (4) | C15—C16—C17—C12 | 0.4 (5) |
C1—Fe1—C6—C7 | 117.9 (2) | N1—C11—C18—C19 | 81.1 (4) |
C5—Fe1—C6—C7 | 74.6 (2) | C10—C11—C18—C19 | −88.3 (3) |
C8—Fe1—C6—C7 | −37.9 (2) | C18'—C11—C18—C19 | 178.5 (8) |
C9—Fe1—C6—C7 | −81.8 (2) | N1—C11—C18—C23 | −102.2 (4) |
C2—Fe1—C6—C7 | 159.9 (2) | C10—C11—C18—C23 | 88.5 (4) |
C3—Fe1—C6—C7 | −162.8 (5) | C18'—C11—C18—C23 | −4.8 (6) |
C10—Fe1—C6—C7 | −119.7 (3) | C23—C18—C19—C20 | 0.0 |
C4—Fe1—C6—C10 | 158.2 (3) | C11—C18—C19—C20 | 176.7 (4) |
C1—Fe1—C6—C10 | −122.5 (2) | C18—C19—C20—C21 | 0.0 |
C7—Fe1—C6—C10 | 119.7 (3) | C19—C20—C21—C22 | 0.0 |
C5—Fe1—C6—C10 | −165.77 (19) | C20—C21—C22—C23 | 0.0 |
C8—Fe1—C6—C10 | 81.73 (19) | C21—C22—C23—C18 | 0.0 |
C9—Fe1—C6—C10 | 37.89 (17) | C21—C22—C23—Cl2 | −180.0 (3) |
C2—Fe1—C6—C10 | −80.4 (2) | C19—C18—C23—C22 | 0.0 |
C3—Fe1—C6—C10 | −43.1 (5) | C11—C18—C23—C22 | −176.7 (4) |
C10—C6—C7—C8 | 0.6 (3) | C19—C18—C23—Cl2 | 180.0 (3) |
Fe1—C6—C7—C8 | 59.9 (2) | C11—C18—C23—Cl2 | 3.2 (4) |
C10—C6—C7—Fe1 | −59.3 (2) | N1—C11—C18'—C19' | −87.3 (4) |
C4—Fe1—C7—C8 | 78.0 (2) | C10—C11—C18'—C19' | 69.2 (4) |
C1—Fe1—C7—C8 | 159.0 (2) | C18—C11—C18'—C19' | 170.6 (8) |
C5—Fe1—C7—C8 | 118.8 (2) | N1—C11—C18'—C23' | 97.4 (5) |
C6—Fe1—C7—C8 | −118.8 (3) | C10—C11—C18'—C23' | −106.1 (5) |
C9—Fe1—C7—C8 | −37.02 (18) | C18—C11—C18'—C23' | −4.7 (5) |
C2—Fe1—C7—C8 | −176.3 (4) | C23'—C18'—C19'—C20' | 0.0 |
C3—Fe1—C7—C8 | 49.1 (4) | C11—C18'—C19'—C20' | −175.4 (5) |
C10—Fe1—C7—C8 | −81.2 (2) | C18'—C19'—C20'—C21' | 0.0 |
C4—Fe1—C7—C6 | −163.2 (2) | C19'—C20'—C21'—C22' | 0.0 |
C1—Fe1—C7—C6 | −82.2 (2) | C20'—C21'—C22'—C23' | 0.0 |
C5—Fe1—C7—C6 | −122.4 (2) | C21'—C22'—C23'—C18' | 0.0 |
C8—Fe1—C7—C6 | 118.8 (3) | C21'—C22'—C23'—Cl2' | 179.4 (5) |
C9—Fe1—C7—C6 | 81.7 (2) | C19'—C18'—C23'—C22' | 0.0 |
C2—Fe1—C7—C6 | −57.5 (5) | C11—C18'—C23'—C22' | 175.2 (5) |
C3—Fe1—C7—C6 | 167.9 (3) | C19'—C18'—C23'—Cl2' | −179.4 (5) |
C10—Fe1—C7—C6 | 37.59 (19) | C11—C18'—C23'—Cl2' | −4.2 (6) |
C6—C7—C8—C9 | −1.2 (4) |
Experimental details
Crystal data | |
Chemical formula | [Fe(C5H5)(C18H12Cl2N)] |
Mr | 434.13 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 294 |
a, b, c (Å) | 8.226 (3), 17.288 (6), 13.996 (5) |
β (°) | 103.820 (6) |
V (Å3) | 1932.8 (11) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.06 |
Crystal size (mm) | 0.22 × 0.18 × 0.12 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.720, 0.880 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10709, 3918, 2546 |
Rint | 0.037 |
(sin θ/λ)max (Å−1) | 0.625 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.107, 1.04 |
No. of reflections | 3918 |
No. of parameters | 284 |
No. of restraints | 8 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.29, −0.26 |
Computer programs: SMART (Bruker, 1997), SMART, SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.
N1—C11 | 1.259 (4) | C10—C11 | 1.469 (4) |
N1—C12 | 1.413 (4) | C11—C18 | 1.510 (4) |
C6—C10 | 1.431 (4) | ||
C11—N1—C12 | 123.3 (3) | N1—C11—C18 | 123.1 (3) |
N1—C11—C10 | 119.2 (3) | C17—C12—N1 | 120.5 (3) |
C12—N1—C11—C10 | −174.0 (3) | C11—N1—C12—C13 | −99.2 (4) |
C12—N1—C11—C18 | 16.9 (5) | N1—C11—C18—C19 | 81.1 (4) |
C6—C10—C11—N1 | 175.1 (3) |
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Some Schiff bases bearing a ferrocenyl group, and their complexes, are excellent non-linear optical materials and liquid crystals (Colbert et al., 1995) because of their strong electron donors and electron-flow bridges. In the course of our investigation of the coordination of Schiff bases with transition metal salts, we observed that the novel title compound, (I), coordinates readily with NiII and CuII salts. The crystal structure of (I) is reported here (Fig. 1).
In (I), the N1–C1 bond length [1.259 (4) Å] confirms that it is a C═N double bond. The torsion angle C6—C10—C11—N1 is 175.1 (3)°, indicating that the imino moiety is nearly in the plane of substituted cyclopentadienyl ring. A certain angle between the two benzene rings mostly because of ortho-chlorine effect [Please clarify] [C11—N1—C12—C13 = −99.2 (4)° and N1—C11—C18—C19 = 81.1 (4)°]. There are no obvious intermolecular interactions between molecules.