Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
The title compound, [Fe(C5H5)(C18H12Cl2N)], a new Schiff base containing a ferrocenyl (Fc) group, has been synthesized and characterized structurally. The compound is a trans isomer. The CFc-C-N-C linkage has a near-planar geometry, indicating conjugation. There are no obvious inter­molecular inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805038730/rn6073sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805038730/rn6073Isup2.hkl
Contains datablock I

CCDC reference: 296633

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](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

Comment top

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 CN 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.

Experimental top

[(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%.

Refinement top

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).

Computing details top

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.

Figures top
[Figure 1] Fig. 1. The structure of (I), with the atom-labelling scheme. Displacement ellipsoids are drawn at the 35% probability level. H atoms are shown as small spheres of arbitrary radii (the disorder was deleted in order to clarify the structure).
1-[(2-Chlorophenyl)(4-chlorophenylimino)methyl]ferrocene top
Crystal data top
[Fe(C5H5)(C18H12Cl2N)]Dx = 1.492 Mg m3
Mr = 434.13Melting point: 446 K
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 8.226 (3) ÅCell parameters from 2747 reflections
b = 17.288 (6) Åθ = 2.8–23.1°
c = 13.996 (5) ŵ = 1.06 mm1
β = 103.820 (6)°T = 294 K
V = 1932.8 (11) Å3Prism, red
Z = 40.22 × 0.18 × 0.12 mm
F(000) = 888
Data collection top
Bruker SMART CCD area-detector
diffractometer
3918 independent reflections
Radiation source: fine-focus sealed tube2546 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
ϕ and ω scansθmax = 26.4°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 710
Tmin = 0.720, Tmax = 0.880k = 2121
10709 measured reflectionsl = 1716
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H-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 parametersΔρmax = 0.29 e Å3
8 restraintsΔρmin = 0.26 e Å3
Crystal data top
[Fe(C5H5)(C18H12Cl2N)]V = 1932.8 (11) Å3
Mr = 434.13Z = 4
Monoclinic, P21/nMo Kα radiation
a = 8.226 (3) ŵ = 1.06 mm1
b = 17.288 (6) ÅT = 294 K
c = 13.996 (5) Å0.22 × 0.18 × 0.12 mm
β = 103.820 (6)°
Data collection top
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 = 0.880Rint = 0.037
10709 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0428 restraints
wR(F2) = 0.107H-atom parameters constrained
S = 1.04Δρmax = 0.29 e Å3
3918 reflectionsΔρmin = 0.26 e Å3
284 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Fe10.04210 (5)1.15546 (2)0.80381 (3)0.04694 (15)
Cl10.20257 (12)0.61035 (5)0.96107 (7)0.0748 (3)
N10.1753 (4)0.95056 (15)0.9168 (2)0.0706 (8)
C10.0892 (4)1.1548 (2)0.6610 (3)0.0729 (11)
H1A0.04471.14230.60390.087*
C20.1608 (4)1.1020 (2)0.7159 (3)0.0703 (10)
H2A0.17331.04620.70400.084*
C30.2093 (4)1.1428 (2)0.7915 (3)0.0711 (10)
H3A0.26251.12100.84110.085*
C40.1676 (4)1.2211 (2)0.7821 (3)0.0674 (9)
H4A0.18661.26330.82490.081*
C50.0951 (4)1.2289 (2)0.7023 (3)0.0705 (10)
H5A0.05531.27710.67910.085*
C60.2883 (4)1.13291 (17)0.8111 (2)0.0528 (8)
H6A0.33671.12150.75510.063*
C70.2689 (4)1.20758 (18)0.8491 (3)0.0620 (9)
H7A0.30251.25660.82440.074*
C80.1939 (4)1.19857 (19)0.9295 (3)0.0663 (10)
H8A0.16521.24070.96940.080*
C90.1627 (4)1.11882 (18)0.9411 (2)0.0580 (8)
H9A0.11011.09620.99050.070*
C100.2231 (4)1.07724 (16)0.8678 (2)0.0469 (7)
C110.2273 (3)0.99278 (16)0.8571 (2)0.0466 (7)
C120.1885 (4)0.86908 (17)0.9181 (2)0.0535 (8)
C130.0524 (4)0.8229 (2)0.8733 (3)0.0650 (9)
H13A0.04330.84570.83460.078*
C140.0583 (4)0.74411 (19)0.8857 (3)0.0621 (9)
H14A0.03270.71380.85520.075*
C150.1983 (4)0.71032 (16)0.9430 (2)0.0495 (7)
C160.3343 (4)0.75422 (18)0.9866 (2)0.0549 (8)
H16A0.42970.73081.02470.066*
C170.3288 (4)0.83326 (18)0.9737 (2)0.0573 (8)
H17A0.42160.86291.00310.069*
Cl20.5914 (3)0.96401 (14)0.86150 (15)0.0764 (7)0.609 (3)
C180.2665 (5)0.9622 (2)0.7640 (2)0.0442 (14)0.609 (3)
C190.1374 (4)0.9503 (3)0.6809 (3)0.062 (2)0.609 (3)
H19A0.02700.95870.68370.075*0.609 (3)
C200.1734 (6)0.9259 (2)0.5936 (2)0.0709 (19)0.609 (3)
H20A0.08710.91800.53800.085*0.609 (3)
C210.3385 (7)0.9133 (2)0.5894 (3)0.0645 (16)0.609 (3)
H21A0.36260.89700.53100.077*0.609 (3)
C220.4675 (5)0.9252 (3)0.6725 (4)0.062 (2)0.609 (3)
H22A0.57800.91680.66970.074*0.609 (3)
C230.4315 (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)
H19B0.55470.98970.91120.059*0.391 (3)
C20'0.6421 (6)0.9504 (4)0.7968 (6)0.067 (3)0.391 (3)
H20B0.75520.95530.82720.080*0.391 (3)
C21'0.5931 (9)0.9225 (4)0.7011 (6)0.074 (3)0.391 (3)
H21B0.67350.90870.66750.089*0.391 (3)
C22'0.4240 (11)0.9152 (4)0.6557 (4)0.062 (4)0.391 (3)
H22B0.39120.89650.59170.075*0.391 (3)
C23'0.3039 (7)0.9358 (4)0.7061 (4)0.058 (2)0.391 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0467 (3)0.0469 (3)0.0449 (3)0.00305 (19)0.00632 (18)0.0010 (2)
Cl10.0898 (7)0.0514 (5)0.0868 (7)0.0089 (4)0.0281 (5)0.0046 (4)
N10.102 (2)0.0446 (16)0.080 (2)0.0120 (15)0.0497 (19)0.0019 (15)
C10.057 (2)0.112 (3)0.0446 (19)0.001 (2)0.0008 (16)0.001 (2)
C20.056 (2)0.069 (2)0.078 (3)0.0095 (18)0.0011 (19)0.009 (2)
C30.053 (2)0.080 (3)0.082 (3)0.0008 (18)0.0199 (18)0.012 (2)
C40.055 (2)0.070 (2)0.074 (3)0.0139 (18)0.0089 (18)0.0047 (19)
C50.064 (2)0.068 (2)0.069 (3)0.0063 (18)0.0034 (19)0.021 (2)
C60.0434 (17)0.0512 (18)0.059 (2)0.0020 (14)0.0039 (15)0.0040 (15)
C70.055 (2)0.0481 (19)0.074 (2)0.0031 (15)0.0022 (18)0.0057 (16)
C80.079 (2)0.051 (2)0.057 (2)0.0130 (17)0.0074 (18)0.0149 (16)
C90.075 (2)0.0521 (19)0.0418 (18)0.0166 (16)0.0047 (16)0.0026 (14)
C100.0479 (17)0.0475 (17)0.0415 (17)0.0080 (14)0.0031 (13)0.0044 (13)
C110.0468 (17)0.0475 (17)0.0430 (17)0.0061 (14)0.0056 (14)0.0018 (14)
C120.066 (2)0.0490 (18)0.0523 (19)0.0068 (16)0.0279 (17)0.0021 (14)
C130.059 (2)0.067 (2)0.065 (2)0.0141 (18)0.0063 (17)0.0024 (18)
C140.051 (2)0.062 (2)0.070 (2)0.0045 (16)0.0075 (17)0.0088 (17)
C150.0519 (19)0.0455 (17)0.0541 (19)0.0040 (14)0.0188 (15)0.0013 (14)
C160.0509 (19)0.055 (2)0.057 (2)0.0047 (15)0.0093 (15)0.0009 (15)
C170.0530 (19)0.052 (2)0.068 (2)0.0063 (15)0.0167 (16)0.0105 (16)
Cl20.0525 (13)0.1004 (14)0.0704 (12)0.0020 (9)0.0029 (9)0.0074 (10)
C180.049 (4)0.038 (3)0.042 (4)0.006 (3)0.006 (3)0.002 (3)
C190.076 (6)0.061 (4)0.050 (5)0.007 (3)0.017 (4)0.025 (3)
C200.100 (6)0.063 (4)0.042 (4)0.004 (3)0.001 (3)0.021 (3)
C210.095 (5)0.046 (3)0.059 (4)0.001 (3)0.030 (4)0.013 (3)
C220.078 (6)0.047 (5)0.069 (5)0.008 (4)0.035 (5)0.003 (4)
C230.056 (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)
Geometric parameters (Å, º) top
Fe1—C42.026 (3)C11—C18'1.517 (5)
Fe1—C12.032 (3)C12—C171.376 (4)
Fe1—C72.032 (3)C12—C131.396 (4)
Fe1—C52.033 (3)C13—C141.372 (4)
Fe1—C82.040 (3)C13—H13A0.9300
Fe1—C62.041 (3)C14—C151.367 (4)
Fe1—C92.041 (3)C14—H14A0.9300
Fe1—C22.043 (3)C15—C161.369 (4)
Fe1—C32.045 (3)C16—C171.378 (4)
Fe1—C102.052 (3)C16—H16A0.9300
Cl1—C151.746 (3)C17—H17A0.9300
N1—C111.259 (4)Cl2—C231.710 (4)
N1—C121.413 (4)C18—C191.3900
C1—C21.409 (5)C18—C231.3900
C1—C51.411 (5)C19—C201.3900
C1—H1A0.9800C19—H19A0.9300
C2—C31.406 (5)C20—C211.3900
C2—H2A0.9800C20—H20A0.9300
C3—C41.410 (5)C21—C221.3900
C3—H3A0.9800C21—H21A0.9300
C4—C51.392 (5)C22—C231.3900
C4—H4A0.9800C22—H22A0.9300
C5—H5A0.9800Cl2'—C23'1.709 (6)
C6—C71.419 (4)C18'—C19'1.3900
C6—C101.431 (4)C18'—C23'1.3900
C6—H6A0.9800C19'—C20'1.3900
C7—C81.416 (5)C19'—H19B0.9300
C7—H7A0.9800C20'—C21'1.3900
C8—C91.419 (4)C20'—H20B0.9300
C8—H8A0.9800C21'—C22'1.3900
C9—C101.435 (4)C21'—H21B0.9300
C9—H9A0.9800C22'—C23'1.3900
C10—C111.469 (4)C22'—H22B0.9300
C11—C181.510 (4)
C4—Fe1—C167.80 (15)C8—C7—Fe169.94 (19)
C4—Fe1—C7118.93 (14)C6—C7—Fe169.94 (17)
C1—Fe1—C7122.82 (16)C8—C7—H7A126.1
C4—Fe1—C540.10 (14)C6—C7—H7A126.1
C1—Fe1—C540.62 (14)Fe1—C7—H7A126.1
C7—Fe1—C5104.84 (15)C7—C8—C9108.8 (3)
C4—Fe1—C8104.39 (14)C7—C8—Fe169.37 (18)
C1—Fe1—C8157.30 (16)C9—C8—Fe169.70 (17)
C7—Fe1—C840.70 (13)C7—C8—H8A125.6
C5—Fe1—C8119.84 (15)C9—C8—H8A125.6
C4—Fe1—C6156.00 (14)Fe1—C8—H8A125.6
C1—Fe1—C6109.64 (14)C8—C9—C10107.6 (3)
C7—Fe1—C640.78 (12)C8—C9—Fe169.61 (18)
C5—Fe1—C6122.19 (15)C10—C9—Fe169.87 (17)
C8—Fe1—C668.34 (14)C8—C9—H9A126.2
C4—Fe1—C9121.33 (14)C10—C9—H9A126.2
C1—Fe1—C9161.54 (15)Fe1—C9—H9A126.2
C7—Fe1—C968.94 (14)C6—C10—C9107.4 (3)
C5—Fe1—C9156.19 (14)C6—C10—C11126.2 (3)
C8—Fe1—C940.69 (13)C9—C10—C11126.3 (3)
C6—Fe1—C968.92 (13)C6—C10—Fe169.14 (16)
C4—Fe1—C267.62 (15)C9—C10—Fe169.07 (16)
C1—Fe1—C240.47 (14)C11—C10—Fe1130.0 (2)
C7—Fe1—C2161.04 (16)N1—C11—C10119.2 (3)
C5—Fe1—C267.95 (15)N1—C11—C18123.1 (3)
C8—Fe1—C2158.20 (17)C10—C11—C18116.8 (3)
C6—Fe1—C2127.02 (14)N1—C11—C18'121.8 (3)
C9—Fe1—C2124.73 (15)C10—C11—C18'114.6 (3)
C4—Fe1—C340.53 (13)C18—C11—C18'29.8 (2)
C1—Fe1—C368.13 (15)C17—C12—C13118.1 (3)
C7—Fe1—C3155.25 (15)C17—C12—N1120.5 (3)
C5—Fe1—C368.08 (15)C13—C12—N1120.9 (3)
C8—Fe1—C3120.65 (16)C14—C13—C12120.7 (3)
C6—Fe1—C3162.75 (14)C14—C13—H13A119.6
C9—Fe1—C3107.46 (15)C12—C13—H13A119.6
C2—Fe1—C340.24 (14)C15—C14—C13119.8 (3)
C4—Fe1—C10159.66 (14)C15—C14—H14A120.1
C1—Fe1—C10125.81 (14)C13—C14—H14A120.1
C7—Fe1—C1068.88 (12)C14—C15—C16120.6 (3)
C5—Fe1—C10160.02 (15)C14—C15—Cl1119.5 (2)
C8—Fe1—C1068.50 (12)C16—C15—Cl1119.9 (2)
C6—Fe1—C1040.92 (12)C15—C16—C17119.6 (3)
C9—Fe1—C1041.06 (11)C15—C16—H16A120.2
C2—Fe1—C10111.58 (13)C17—C16—H16A120.2
C3—Fe1—C10125.44 (13)C12—C17—C16121.1 (3)
C11—N1—C12123.3 (3)C12—C17—H17A119.4
C2—C1—C5107.7 (3)C16—C17—H17A119.4
C2—C1—Fe170.2 (2)C19—C18—C23120.0
C5—C1—Fe169.74 (19)C19—C18—C11119.7 (3)
C2—C1—H1A126.1C23—C18—C11120.2 (3)
C5—C1—H1A126.1C20—C19—C18120.0
Fe1—C1—H1A126.1C20—C19—H19A120.0
C3—C2—C1108.4 (3)C18—C19—H19A120.0
C3—C2—Fe170.0 (2)C19—C20—C21120.0
C1—C2—Fe169.35 (19)C19—C20—H20A120.0
C3—C2—H2A125.8C21—C20—H20A120.0
C1—C2—H2A125.8C22—C21—C20120.0
Fe1—C2—H2A125.8C22—C21—H21A120.0
C2—C3—C4107.0 (3)C20—C21—H21A120.0
C2—C3—Fe169.78 (19)C21—C22—C23120.0
C4—C3—Fe169.02 (19)C21—C22—H22A120.0
C2—C3—H3A126.5C23—C22—H22A120.0
C4—C3—H3A126.5C22—C23—C18120.0
Fe1—C3—H3A126.5C22—C23—Cl2119.5 (3)
C5—C4—C3109.1 (3)C18—C23—Cl2120.5 (3)
C5—C4—Fe170.22 (19)C19'—C18'—C23'120.0
C3—C4—Fe170.45 (19)C19'—C18'—C11117.8 (5)
C5—C4—H4A125.4C23'—C18'—C11122.1 (5)
C3—C4—H4A125.4C18'—C19'—C20'120.0
Fe1—C4—H4A125.4C18'—C19'—H19B120.0
C4—C5—C1107.7 (3)C20'—C19'—H19B120.0
C4—C5—Fe169.69 (19)C21'—C20'—C19'120.0
C1—C5—Fe169.64 (19)C21'—C20'—H20B120.0
C4—C5—H5A126.1C19'—C20'—H20B120.0
C1—C5—H5A126.1C20'—C21'—C22'120.0
Fe1—C5—H5A126.1C20'—C21'—H21B120.0
C7—C6—C10108.3 (3)C22'—C21'—H21B120.0
C7—C6—Fe169.28 (17)C23'—C22'—C21'120.0
C10—C6—Fe169.95 (17)C23'—C22'—H22B120.0
C7—C6—H6A125.9C21'—C22'—H22B120.0
C10—C6—H6A125.9C22'—C23'—C18'120.0
Fe1—C6—H6A125.9C22'—C23'—Cl2'119.4 (5)
C8—C7—C6107.9 (3)C18'—C23'—Cl2'120.6 (5)
C4—Fe1—C1—C281.1 (2)Fe1—C7—C8—C958.7 (2)
C7—Fe1—C1—C2167.9 (2)C6—C7—C8—Fe159.9 (2)
C5—Fe1—C1—C2118.6 (3)C4—Fe1—C8—C7117.9 (2)
C8—Fe1—C1—C2154.8 (3)C1—Fe1—C8—C751.3 (4)
C6—Fe1—C1—C2124.5 (2)C5—Fe1—C8—C777.6 (2)
C9—Fe1—C1—C242.4 (5)C6—Fe1—C8—C738.03 (18)
C3—Fe1—C1—C237.2 (2)C9—Fe1—C8—C7120.5 (3)
C10—Fe1—C1—C281.6 (3)C2—Fe1—C8—C7176.8 (3)
C4—Fe1—C1—C537.5 (2)C3—Fe1—C8—C7158.40 (19)
C7—Fe1—C1—C573.5 (3)C10—Fe1—C8—C782.2 (2)
C8—Fe1—C1—C536.3 (5)C4—Fe1—C8—C9121.7 (2)
C6—Fe1—C1—C5116.9 (2)C1—Fe1—C8—C9171.7 (3)
C9—Fe1—C1—C5160.9 (4)C7—Fe1—C8—C9120.5 (3)
C2—Fe1—C1—C5118.6 (3)C5—Fe1—C8—C9161.9 (2)
C3—Fe1—C1—C581.4 (2)C6—Fe1—C8—C982.4 (2)
C10—Fe1—C1—C5159.9 (2)C2—Fe1—C8—C956.3 (4)
C5—C1—C2—C30.6 (4)C3—Fe1—C8—C981.1 (2)
Fe1—C1—C2—C359.3 (2)C10—Fe1—C8—C938.28 (19)
C5—C1—C2—Fe159.9 (2)C7—C8—C9—C101.4 (4)
C4—Fe1—C2—C338.2 (2)Fe1—C8—C9—C1059.8 (2)
C1—Fe1—C2—C3119.8 (3)C7—C8—C9—Fe158.5 (2)
C7—Fe1—C2—C3152.5 (4)C4—Fe1—C9—C874.8 (2)
C5—Fe1—C2—C381.7 (2)C1—Fe1—C9—C8169.9 (4)
C8—Fe1—C2—C334.0 (5)C7—Fe1—C9—C837.0 (2)
C6—Fe1—C2—C3163.8 (2)C5—Fe1—C9—C841.8 (4)
C9—Fe1—C2—C375.3 (3)C6—Fe1—C9—C880.9 (2)
C10—Fe1—C2—C3119.9 (2)C2—Fe1—C9—C8157.9 (2)
C4—Fe1—C2—C181.6 (2)C3—Fe1—C9—C8117.0 (2)
C7—Fe1—C2—C132.7 (5)C10—Fe1—C9—C8118.6 (3)
C5—Fe1—C2—C138.1 (2)C4—Fe1—C9—C10166.51 (19)
C8—Fe1—C2—C1153.8 (3)C1—Fe1—C9—C1051.3 (5)
C6—Fe1—C2—C176.4 (3)C7—Fe1—C9—C1081.6 (2)
C9—Fe1—C2—C1164.9 (2)C5—Fe1—C9—C10160.5 (3)
C3—Fe1—C2—C1119.8 (3)C8—Fe1—C9—C10118.6 (3)
C10—Fe1—C2—C1120.4 (2)C6—Fe1—C9—C1037.77 (18)
C1—C2—C3—C40.3 (4)C2—Fe1—C9—C1083.4 (2)
Fe1—C2—C3—C459.2 (2)C3—Fe1—C9—C10124.4 (2)
C1—C2—C3—Fe158.9 (2)C7—C6—C10—C90.2 (3)
C4—Fe1—C3—C2118.4 (3)Fe1—C6—C10—C958.7 (2)
C1—Fe1—C3—C237.4 (2)C7—C6—C10—C11176.2 (3)
C7—Fe1—C3—C2159.0 (3)Fe1—C6—C10—C11125.0 (3)
C5—Fe1—C3—C281.3 (2)C7—C6—C10—Fe158.8 (2)
C8—Fe1—C3—C2166.0 (2)C8—C9—C10—C60.9 (3)
C6—Fe1—C3—C248.5 (6)Fe1—C9—C10—C658.7 (2)
C9—Fe1—C3—C2123.6 (2)C8—C9—C10—C11175.4 (3)
C10—Fe1—C3—C281.8 (3)Fe1—C9—C10—C11125.0 (3)
C1—Fe1—C3—C481.0 (2)C8—C9—C10—Fe159.6 (2)
C7—Fe1—C3—C440.6 (5)C4—Fe1—C10—C6154.2 (4)
C5—Fe1—C3—C437.0 (2)C1—Fe1—C10—C678.5 (2)
C8—Fe1—C3—C475.6 (3)C7—Fe1—C10—C637.47 (19)
C6—Fe1—C3—C4166.9 (4)C5—Fe1—C10—C637.5 (5)
C9—Fe1—C3—C4118.1 (2)C8—Fe1—C10—C681.3 (2)
C2—Fe1—C3—C4118.4 (3)C9—Fe1—C10—C6119.2 (3)
C10—Fe1—C3—C4159.8 (2)C2—Fe1—C10—C6122.2 (2)
C2—C3—C4—C50.1 (4)C3—Fe1—C10—C6165.6 (2)
Fe1—C3—C4—C559.8 (2)C4—Fe1—C10—C935.0 (5)
C2—C3—C4—Fe159.7 (2)C1—Fe1—C10—C9162.3 (2)
C1—Fe1—C4—C538.0 (2)C7—Fe1—C10—C981.8 (2)
C7—Fe1—C4—C578.3 (3)C5—Fe1—C10—C9156.8 (4)
C8—Fe1—C4—C5119.5 (2)C8—Fe1—C10—C937.9 (2)
C6—Fe1—C4—C550.6 (4)C6—Fe1—C10—C9119.2 (3)
C9—Fe1—C4—C5160.0 (2)C2—Fe1—C10—C9118.6 (2)
C2—Fe1—C4—C581.9 (2)C3—Fe1—C10—C975.2 (2)
C3—Fe1—C4—C5119.8 (3)C4—Fe1—C10—C1185.4 (5)
C10—Fe1—C4—C5173.8 (3)C1—Fe1—C10—C1141.9 (3)
C1—Fe1—C4—C381.8 (2)C7—Fe1—C10—C11157.9 (3)
C7—Fe1—C4—C3161.8 (2)C5—Fe1—C10—C1182.9 (5)
C5—Fe1—C4—C3119.8 (3)C8—Fe1—C10—C11158.3 (3)
C8—Fe1—C4—C3120.7 (2)C6—Fe1—C10—C11120.4 (3)
C6—Fe1—C4—C3170.5 (3)C9—Fe1—C10—C11120.4 (4)
C9—Fe1—C4—C380.1 (3)C2—Fe1—C10—C111.8 (3)
C2—Fe1—C4—C337.9 (2)C3—Fe1—C10—C1145.2 (3)
C10—Fe1—C4—C354.0 (5)C12—N1—C11—C10174.0 (3)
C3—C4—C5—C10.5 (4)C12—N1—C11—C1816.9 (5)
Fe1—C4—C5—C159.5 (2)C12—N1—C11—C18'18.5 (6)
C3—C4—C5—Fe159.9 (2)C6—C10—C11—N1175.1 (3)
C2—C1—C5—C40.7 (4)C9—C10—C11—N10.6 (5)
Fe1—C1—C5—C459.5 (2)Fe1—C10—C11—N192.7 (3)
C2—C1—C5—Fe160.2 (2)C6—C10—C11—C1815.2 (4)
C1—Fe1—C5—C4118.9 (3)C9—C10—C11—C18169.2 (3)
C7—Fe1—C5—C4117.5 (2)Fe1—C10—C11—C1877.0 (4)
C8—Fe1—C5—C476.3 (3)C6—C10—C11—C18'17.9 (5)
C6—Fe1—C5—C4158.2 (2)C9—C10—C11—C18'157.8 (4)
C9—Fe1—C5—C446.2 (5)Fe1—C10—C11—C18'110.1 (4)
C2—Fe1—C5—C481.0 (2)C11—N1—C12—C1788.9 (4)
C3—Fe1—C5—C437.4 (2)C11—N1—C12—C1399.2 (4)
C10—Fe1—C5—C4173.7 (3)C17—C12—C13—C140.8 (5)
C4—Fe1—C5—C1118.9 (3)N1—C12—C13—C14171.3 (3)
C7—Fe1—C5—C1123.5 (2)C12—C13—C14—C150.4 (5)
C8—Fe1—C5—C1164.7 (2)C13—C14—C15—C161.3 (5)
C6—Fe1—C5—C182.9 (2)C13—C14—C15—Cl1178.2 (3)
C9—Fe1—C5—C1165.2 (3)C14—C15—C16—C170.9 (5)
C2—Fe1—C5—C138.0 (2)Cl1—C15—C16—C17178.6 (2)
C3—Fe1—C5—C181.5 (2)C13—C12—C17—C161.2 (5)
C10—Fe1—C5—C154.8 (5)N1—C12—C17—C16170.9 (3)
C4—Fe1—C6—C738.5 (4)C15—C16—C17—C120.4 (5)
C1—Fe1—C6—C7117.9 (2)N1—C11—C18—C1981.1 (4)
C5—Fe1—C6—C774.6 (2)C10—C11—C18—C1988.3 (3)
C8—Fe1—C6—C737.9 (2)C18'—C11—C18—C19178.5 (8)
C9—Fe1—C6—C781.8 (2)N1—C11—C18—C23102.2 (4)
C2—Fe1—C6—C7159.9 (2)C10—C11—C18—C2388.5 (4)
C3—Fe1—C6—C7162.8 (5)C18'—C11—C18—C234.8 (6)
C10—Fe1—C6—C7119.7 (3)C23—C18—C19—C200.0
C4—Fe1—C6—C10158.2 (3)C11—C18—C19—C20176.7 (4)
C1—Fe1—C6—C10122.5 (2)C18—C19—C20—C210.0
C7—Fe1—C6—C10119.7 (3)C19—C20—C21—C220.0
C5—Fe1—C6—C10165.77 (19)C20—C21—C22—C230.0
C8—Fe1—C6—C1081.73 (19)C21—C22—C23—C180.0
C9—Fe1—C6—C1037.89 (17)C21—C22—C23—Cl2180.0 (3)
C2—Fe1—C6—C1080.4 (2)C19—C18—C23—C220.0
C3—Fe1—C6—C1043.1 (5)C11—C18—C23—C22176.7 (4)
C10—C6—C7—C80.6 (3)C19—C18—C23—Cl2180.0 (3)
Fe1—C6—C7—C859.9 (2)C11—C18—C23—Cl23.2 (4)
C10—C6—C7—Fe159.3 (2)N1—C11—C18'—C19'87.3 (4)
C4—Fe1—C7—C878.0 (2)C10—C11—C18'—C19'69.2 (4)
C1—Fe1—C7—C8159.0 (2)C18—C11—C18'—C19'170.6 (8)
C5—Fe1—C7—C8118.8 (2)N1—C11—C18'—C23'97.4 (5)
C6—Fe1—C7—C8118.8 (3)C10—C11—C18'—C23'106.1 (5)
C9—Fe1—C7—C837.02 (18)C18—C11—C18'—C23'4.7 (5)
C2—Fe1—C7—C8176.3 (4)C23'—C18'—C19'—C20'0.0
C3—Fe1—C7—C849.1 (4)C11—C18'—C19'—C20'175.4 (5)
C10—Fe1—C7—C881.2 (2)C18'—C19'—C20'—C21'0.0
C4—Fe1—C7—C6163.2 (2)C19'—C20'—C21'—C22'0.0
C1—Fe1—C7—C682.2 (2)C20'—C21'—C22'—C23'0.0
C5—Fe1—C7—C6122.4 (2)C21'—C22'—C23'—C18'0.0
C8—Fe1—C7—C6118.8 (3)C21'—C22'—C23'—Cl2'179.4 (5)
C9—Fe1—C7—C681.7 (2)C19'—C18'—C23'—C22'0.0
C2—Fe1—C7—C657.5 (5)C11—C18'—C23'—C22'175.2 (5)
C3—Fe1—C7—C6167.9 (3)C19'—C18'—C23'—Cl2'179.4 (5)
C10—Fe1—C7—C637.59 (19)C11—C18'—C23'—Cl2'4.2 (6)
C6—C7—C8—C91.2 (4)

Experimental details

Crystal data
Chemical formula[Fe(C5H5)(C18H12Cl2N)]
Mr434.13
Crystal system, space groupMonoclinic, P21/n
Temperature (K)294
a, b, c (Å)8.226 (3), 17.288 (6), 13.996 (5)
β (°) 103.820 (6)
V3)1932.8 (11)
Z4
Radiation typeMo Kα
µ (mm1)1.06
Crystal size (mm)0.22 × 0.18 × 0.12
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.720, 0.880
No. of measured, independent and
observed [I > 2σ(I)] reflections
10709, 3918, 2546
Rint0.037
(sin θ/λ)max1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.107, 1.04
No. of reflections3918
No. of parameters284
No. of restraints8
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.29, 0.26

Computer programs: SMART (Bruker, 1997), SMART, SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.

Selected geometric parameters (Å, º) top
N1—C111.259 (4)C10—C111.469 (4)
N1—C121.413 (4)C11—C181.510 (4)
C6—C101.431 (4)
C11—N1—C12123.3 (3)N1—C11—C18123.1 (3)
N1—C11—C10119.2 (3)C17—C12—N1120.5 (3)
C12—N1—C11—C10174.0 (3)C11—N1—C12—C1399.2 (4)
C12—N1—C11—C1816.9 (5)N1—C11—C18—C1981.1 (4)
C6—C10—C11—N1175.1 (3)
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds