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The crystal structure of [2-(4-bromo­phenyl)-4-cyano-5-ferrocenyl­pyrazolo­[2,3-a]­pyridin-7-yl]­aceto­nitrile, C26H17N4FeBr or [Fe(C5H5)(C21H12BrN4)], shows that the pyrazolo­pyridine ring system (PP), the bromo­phenyl ring (BP) and the cyclo­penta­diene ring (Cp) are nearly planar. The PP ring system is twisted out of the plane of the BP and Cp rings by about 20°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100002535/qb0178sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100002535/qb0178Isup2.hkl
Contains datablock I

CCDC reference: 143326

Comment top

In view of the recent growing interest in the field of asymmetric synthesis, ferrocene and its derivatives occupy an important place in synthetic and materials chemistry due to their unique non-linear optical, liquid and crystalline and ferromagnetic properties (Hayashi, 1995). The 1,2- and 1,3-disubstituted ferrocene derivatives, having planar chirality, are suitable chiral reference systems for asymmetric induced synthesis (Marquarding et al., 1970). The unique properties of these compounds encouraged the synthesis of ferrocene derivatives with highly functionalized ring systems directly linked to one of the cyclopentadiene moieties. These compounds do not exhibit optical activity due to lack of restricted rotation. The title compound was synthesized following a procedure reported earlier (Nath et al., 1998). The structure of the title compound, (I), was assigned by IR, NMR and mass spectra, but the conformation of the ferrocene moiety with respect to the heterocyclic ring was of particular interest and prompted us to undertake the present X-ray diffraction study.

The title molecule contains one pyrazolo[2,3-a]pyridine fused-ring system (PP), one bromo-phenyl ring (BP) and one ferrocenyl moiety. The two individual rings [inclined to each other by an angle 1.9 (2)°] in the PP system and the BP ring are planar [the deviations of the atoms from the least-squares planes are within the range -0.012 (3)–0.006 (3) Å]. The –CN group at C12 lies slightly out of the PP ring system [torsion angle C6—C7—C12—C13 - 7.2 (6)°]. The cyclopentadiene rings of the ferrocene moiety are essentually elipsed [the mean value of the five torsion angles CnA—CgA—CgB—CnB (where n = 1–5, and CgA and CgB are the Cp ring centroids) is 4.9 (6)°]. The Cp rings are parallel [dihedral angle 2.4 (3)°] and each lies equidistant [1.65 (1) Å] from the Fe atom. Both the BP and Cp rings adopt a twist conformation with respect to the PP ring system [torsion angle N1—C2—C1'—C6' -17.8 (6)° and C6—C5—C1A—C5A 20.6 (6)°]. There are no short contacts or intermolecular stacking interactions in the lattice.

Experimental top

The synthesis of (I) was carried out by the reaction of 3-cyano-6-ferrocenyl-4-methylthio-2H-pyran-2-one with 5-(4-bromophenyl)-3-cyanomethyl-1H-pyrazole in a 1:1 molar ratio in dry DMF in the presence of KOH (Nath et al., 1998). Diffraction quality crystals were grown by slow evaporation from a mixture of dichloromethane and hexane at room temperature.

Refinement top

All H atoms were placed in geometrically idealized positions and allowed to ride on their parent atoms, to which each was bonded for the final cycles of refinement. Nine reflections [most disagreeable, Δ(F2)/σ > 5.0] were suppressed during the last cycles of refinement.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL93 (Sheldrick, 1993); molecular graphics: NRCVAX (Gabe et al., 1989); software used to prepare material for publication: SHELXL93.

2-[(4-Bromophenyl)-4-cyano-5-ferrocenylpyrazolo[1,5-a]pyridin-7yl] acetonitrile top
Crystal data top
[Fe(C5H5)(C21H12BrN4)]F(000) = 524
Mr = 521.20Dx = 1.628 Mg m3
Triclinic, P1Melting point: 230 K
a = 7.9608 (1) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.6844 (1) ÅCell parameters from 509 reflections
c = 12.8215 (3) Åθ = 3.0–25.6°
α = 93.577 (1)°µ = 2.61 mm1
β = 97.737 (1)°T = 150 K
γ = 99.046 (1)°Plate, red
V = 1063.28 (3) Å30.25 × 0.15 × 0.06 mm
Z = 2
Data collection top
Bruker SMARTCCD
diffractometer
4823 independent reflections
Radiation source: fine-focus sealed tube3953 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
ω scansθmax = 27.5°, θmin = 1.6°
Absorption correction: ψ scan
(XPREP; Sheldrick, 1994)
h = 109
Tmin = 0.606, Tmax = 0.855k = 1310
7790 measured reflectionsl = 1616
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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140H-atom parameters constrained
S = 1.03Calculated w = 1/[σ2(Fo2) + (0.0381P)2 + 4.8638P]
where P = (Fo2 + 2Fc2)/3
4783 reflections(Δ/σ)max = 0.001
289 parametersΔρmax = 0.46 e Å3
0 restraintsΔρmin = 0.36 e Å3
Crystal data top
[Fe(C5H5)(C21H12BrN4)]γ = 99.046 (1)°
Mr = 521.20V = 1063.28 (3) Å3
Triclinic, P1Z = 2
a = 7.9608 (1) ÅMo Kα radiation
b = 10.6844 (1) ŵ = 2.61 mm1
c = 12.8215 (3) ÅT = 150 K
α = 93.577 (1)°0.25 × 0.15 × 0.06 mm
β = 97.737 (1)°
Data collection top
Bruker SMARTCCD
diffractometer
4823 independent reflections
Absorption correction: ψ scan
(XPREP; Sheldrick, 1994)
3953 reflections with I > 2σ(I)
Tmin = 0.606, Tmax = 0.855Rint = 0.040
7790 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.140H-atom parameters constrained
S = 1.03Δρmax = 0.46 e Å3
4783 reflectionsΔρmin = 0.36 e Å3
289 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 on F2 for ALL reflections except for 40 with very negative F2 or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating _R_factor_obs 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*/Ueq
Br0.44869 (6)0.74199 (5)0.35615 (3)0.03315 (14)
Fe1.00953 (8)1.43332 (6)1.27215 (5)0.0236 (2)
N11.0036 (4)1.0849 (3)0.7807 (3)0.0212 (7)
C20.8354 (5)1.0328 (4)0.7704 (3)0.0227 (8)
C1'0.7432 (5)0.9683 (4)0.6690 (3)0.0225 (8)
C2'0.5900 (5)0.8835 (4)0.6689 (3)0.0265 (9)
H2'0.54730.87090.73210.032*
C3'0.5009 (5)0.8177 (4)0.5759 (3)0.0274 (9)
H3'0.39850.76210.57610.033*
C4'0.5687 (5)0.8370 (4)0.4824 (3)0.0253 (9)
C5'0.7189 (5)0.9210 (4)0.4792 (3)0.0268 (9)
H5'0.76070.93330.41560.032*
C6'0.8064 (5)0.9868 (4)0.5733 (3)0.0259 (9)
H6'0.90751.04350.57240.031*
C30.7656 (5)1.0495 (4)0.8640 (3)0.0211 (8)
H30.65311.02170.87490.025*
C40.9184 (5)1.1670 (4)1.0441 (3)0.0208 (8)
C51.0748 (5)1.2339 (4)1.0944 (3)0.0223 (8)
C1A1.1057 (5)1.2849 (4)1.2055 (3)0.0221 (8)
C2A1.0095 (6)1.2438 (4)1.2890 (3)0.0279 (9)
H2A0.91291.18061.28160.034*
C3A1.0890 (6)1.3172 (4)1.3849 (3)0.0317 (10)
H3A1.05361.30951.45070.038*
C4A1.2314 (6)1.4041 (4)1.3624 (3)0.0288 (9)
H4A1.30441.46351.41090.035*
C5A1.2430 (5)1.3848 (4)1.2530 (3)0.0245 (8)
H5A1.32541.42911.21790.029*
C1B0.8700 (7)1.5064 (5)1.1520 (4)0.0410 (12)
H1B0.85551.47911.08060.049*
C2B0.7626 (6)1.4611 (5)1.2255 (5)0.0456 (14)
H2B0.66571.39821.21090.055*
C3B0.8282 (7)1.5283 (5)1.3255 (5)0.0420 (12)
H3B0.78221.51731.38780.050*
C4B0.9764 (6)1.6150 (4)1.3129 (4)0.0333 (10)
H4B1.04431.67161.36570.040*
C5B1.0040 (6)1.6009 (5)1.2063 (4)0.0344 (10)
H5B1.09371.64551.17700.041*
C61.2138 (5)1.2519 (4)1.0331 (3)0.0219 (8)
H61.31931.29801.06460.026*
C71.1965 (5)1.2038 (4)0.9302 (3)0.0218 (8)
N81.0405 (4)1.1352 (3)0.8837 (3)0.0198 (7)
C90.8985 (5)1.1159 (4)0.9364 (3)0.0204 (8)
C100.7638 (6)1.1435 (4)1.0915 (3)0.0270 (9)
N110.6341 (5)1.1199 (5)1.1207 (3)0.0423 (11)
C121.3299 (5)1.2185 (4)0.8572 (3)0.0255 (9)
H12A1.35961.13580.84010.031*
H12B1.28091.24870.79200.031*
C131.4873 (6)1.3068 (5)0.9018 (3)0.0299 (9)
N141.6111 (5)1.3756 (5)0.9303 (3)0.0460 (12)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br0.0301 (2)0.0418 (3)0.0227 (2)0.0025 (2)0.0016 (2)0.0084 (2)
Fe0.0249 (3)0.0244 (3)0.0202 (3)0.0031 (2)0.0017 (2)0.0025 (2)
N10.024 (2)0.021 (2)0.016 (2)0.0013 (13)0.0026 (13)0.0029 (13)
C20.022 (2)0.024 (2)0.021 (2)0.001 (2)0.0004 (15)0.002 (2)
C1'0.020 (2)0.025 (2)0.022 (2)0.007 (2)0.0010 (15)0.000 (2)
C2'0.025 (2)0.033 (2)0.020 (2)0.001 (2)0.004 (2)0.001 (2)
C3'0.020 (2)0.035 (2)0.025 (2)0.000 (2)0.004 (2)0.001 (2)
C4'0.028 (2)0.026 (2)0.019 (2)0.003 (2)0.000 (2)0.004 (2)
C5'0.025 (2)0.034 (2)0.020 (2)0.000 (2)0.005 (2)0.001 (2)
C6'0.026 (2)0.029 (2)0.022 (2)0.000 (2)0.003 (2)0.000 (2)
C30.020 (2)0.025 (2)0.018 (2)0.002 (2)0.0031 (14)0.0007 (15)
C40.022 (2)0.021 (2)0.021 (2)0.003 (2)0.0072 (15)0.0019 (15)
C50.027 (2)0.020 (2)0.020 (2)0.005 (2)0.002 (2)0.004 (2)
C1A0.025 (2)0.025 (2)0.017 (2)0.004 (2)0.0018 (15)0.0014 (15)
C2A0.038 (2)0.024 (2)0.021 (2)0.001 (2)0.005 (2)0.001 (2)
C3A0.044 (3)0.032 (2)0.019 (2)0.006 (2)0.003 (2)0.001 (2)
C4A0.030 (2)0.032 (2)0.022 (2)0.006 (2)0.004 (2)0.002 (2)
C5A0.023 (2)0.026 (2)0.023 (2)0.004 (2)0.000 (2)0.000 (2)
C1B0.049 (3)0.040 (3)0.032 (3)0.023 (2)0.011 (2)0.007 (2)
C2B0.023 (2)0.044 (3)0.065 (4)0.007 (2)0.004 (2)0.017 (3)
C3B0.037 (3)0.040 (3)0.050 (3)0.008 (2)0.014 (2)0.010 (2)
C4B0.036 (2)0.026 (2)0.036 (2)0.005 (2)0.003 (2)0.010 (2)
C5B0.039 (3)0.032 (2)0.036 (3)0.016 (2)0.007 (2)0.006 (2)
C60.019 (2)0.025 (2)0.020 (2)0.0014 (15)0.0011 (14)0.001 (2)
C70.021 (2)0.022 (2)0.022 (2)0.0016 (15)0.0029 (15)0.001 (2)
N80.019 (2)0.022 (2)0.017 (2)0.0016 (13)0.0032 (12)0.0006 (13)
C90.021 (2)0.023 (2)0.018 (2)0.0036 (15)0.0041 (15)0.0044 (15)
C100.027 (2)0.030 (2)0.021 (2)0.002 (2)0.005 (2)0.004 (2)
N110.032 (2)0.059 (3)0.031 (2)0.010 (2)0.012 (2)0.009 (2)
C120.022 (2)0.031 (2)0.023 (2)0.000 (2)0.007 (2)0.002 (2)
C130.030 (2)0.037 (3)0.022 (2)0.001 (2)0.007 (2)0.002 (2)
N140.032 (2)0.066 (3)0.032 (2)0.015 (2)0.006 (2)0.006 (2)
Geometric parameters (Å, º) top
Br—C4'1.907 (4)C5—C1A1.468 (5)
Fe—C5B2.031 (5)C1A—C5A1.441 (6)
Fe—C4B2.045 (4)C1A—C2A1.449 (6)
Fe—C2B2.049 (5)C2A—C3A1.428 (6)
Fe—C1A2.054 (4)C2A—H2A0.93
Fe—C5A2.048 (4)C3A—C4A1.422 (7)
Fe—C2A2.050 (4)C3A—H3A0.93
Fe—C1B2.044 (5)C4A—C5A1.423 (6)
Fe—C4A2.055 (4)C4A—H4A0.93
Fe—C3B2.054 (5)C5A—H5A0.93
Fe—C3A2.062 (5)C1B—C2B1.413 (8)
N1—C21.353 (5)C1B—C5B1.419 (7)
N1—N81.370 (4)C1B—H1B0.93
C2—C31.401 (5)C2B—C3B1.420 (7)
C2—C1'1.475 (5)C2B—H2B0.93
C1'—C2'1.400 (6)C3B—C4B1.415 (7)
C1'—C6'1.402 (6)C3B—H3B0.93
C2'—C3'1.389 (6)C4B—C5B1.416 (7)
C2'—H2'0.93C4B—H4B0.93
C3'—C4'1.394 (6)C5B—H5B0.93
C3'—H3'0.93C6—C71.367 (5)
C4'—C5'1.385 (6)C6—H60.93
C5'—C6'1.396 (6)C7—N81.377 (5)
C5'—H5'0.93C7—C121.503 (5)
C6'—H6'0.93N8—C91.388 (5)
C3—C91.379 (5)C10—N111.142 (6)
C3—H30.93C12—C131.468 (6)
C4—C51.387 (6)C12—H12A0.97
C4—C91.432 (5)C12—H12B0.97
C4—C101.439 (6)C13—N141.134 (6)
C5—C61.436 (6)
C5B—Fe—C4B40.7 (2)C2A—C1A—C5127.5 (4)
C5B—Fe—C2B68.4 (2)C5A—C1A—Fe69.2 (2)
C4B—Fe—C2B67.9 (2)C2A—C1A—Fe69.2 (2)
C5B—Fe—C1A123.2 (2)C5—C1A—Fe127.8 (3)
C4B—Fe—C1A160.3 (2)C3A—C2A—C1A108.1 (4)
C2B—Fe—C1A121.5 (2)C3A—C2A—Fe70.1 (3)
C5B—Fe—C5A105.6 (2)C1A—C2A—Fe69.5 (2)
C4B—Fe—C5A123.4 (2)C3A—C2A—H2A126.0 (3)
C2B—Fe—C5A156.1 (2)C1A—C2A—H2A126.0 (2)
C1A—Fe—C5A41.1 (2)Fe—C2A—H2A126.01 (13)
C5B—Fe—C2A161.7 (2)C4A—C3A—C2A108.4 (4)
C4B—Fe—C2A156.8 (2)C4A—C3A—Fe69.5 (3)
C2B—Fe—C2A109.2 (2)C2A—C3A—Fe69.2 (2)
C1A—Fe—C2A41.4 (2)C4A—C3A—H3A125.8 (2)
C5A—Fe—C2A68.9 (2)C2A—C3A—H3A125.8 (3)
C5B—Fe—C1B40.8 (2)Fe—C3A—H3A127.00 (13)
C4B—Fe—C1B68.1 (2)C5A—C4A—C3A108.3 (4)
C2B—Fe—C1B40.4 (2)C5A—C4A—Fe69.5 (2)
C1A—Fe—C1B106.9 (2)C3A—C4A—Fe70.1 (3)
C5A—Fe—C1B120.1 (2)C5A—C4A—H4A125.8 (2)
C2A—Fe—C1B125.6 (2)C3A—C4A—H4A125.8 (2)
C5B—Fe—C4A119.4 (2)Fe—C4A—H4A126.21 (13)
C4B—Fe—C4A107.0 (2)C4A—C5A—C1A108.6 (4)
C2B—Fe—C4A162.7 (2)C4A—C5A—Fe70.0 (2)
C1A—Fe—C4A68.9 (2)C1A—C5A—Fe69.7 (2)
C5A—Fe—C4A40.6 (2)C4A—C5A—H5A125.7 (2)
C2A—Fe—C4A68.5 (2)C1A—C5A—H5A125.7 (2)
C1B—Fe—C4A154.9 (2)Fe—C5A—H5A126.25 (12)
C5B—Fe—C3B68.4 (2)C2B—C1B—C5B108.1 (4)
C4B—Fe—C3B40.4 (2)C2B—C1B—Fe70.0 (3)
C2B—Fe—C3B40.5 (2)C5B—C1B—Fe69.1 (3)
C1A—Fe—C3B157.4 (2)C2B—C1B—H1B126.0 (3)
C5A—Fe—C3B160.8 (2)C5B—C1B—H1B126.0 (3)
C2A—Fe—C3B122.3 (2)Fe—C1B—H1B126.47 (14)
C1B—Fe—C3B68.1 (2)C3B—C2B—C1B108.2 (5)
C4A—Fe—C3B125.1 (2)C3B—C2B—Fe69.9 (3)
C5B—Fe—C3A155.2 (2)C1B—C2B—Fe69.6 (3)
C4B—Fe—C3A121.3 (2)C3B—C2B—H2B125.9 (3)
C2B—Fe—C3A126.8 (2)C1B—C2B—H2B125.9 (3)
C1A—Fe—C3A68.9 (2)Fe—C2B—H2B126.1 (2)
C5A—Fe—C3A68.3 (2)C4B—C3B—C2B107.5 (5)
C2A—Fe—C3A40.6 (2)C4B—C3B—Fe69.4 (3)
C1B—Fe—C3A163.2 (2)C2B—C3B—Fe69.5 (3)
C4A—Fe—C3A40.4 (2)C4B—C3B—H3B126.2 (3)
C3B—Fe—C3A109.0 (2)C2B—C3B—H3B126.2 (3)
C2—N1—N8103.5 (3)Fe—C3B—H3B126.3 (2)
N1—C2—C3112.5 (3)C3B—C4B—C5B108.5 (4)
N1—C2—C1'121.1 (4)C3B—C4B—Fe70.2 (3)
C3—C2—C1'126.4 (4)C5B—C4B—Fe69.2 (3)
C2'—C1'—C6'119.0 (4)C3B—C4B—H4B125.7 (3)
C2'—C1'—C2118.9 (4)C5B—C4B—H4B125.7 (3)
C6'—C1'—C2122.0 (4)Fe—C4B—H4B126.50 (13)
C3'—C2'—C1'121.2 (4)C4B—C5B—C1B107.6 (5)
C3'—C2'—H2'119.4 (2)C4B—C5B—Fe70.2 (3)
C1'—C2'—H2'119.4 (2)C1B—C5B—Fe70.1 (3)
C2'—C3'—C4'118.3 (4)C4B—C5B—H5B126.2 (3)
C2'—C3'—H3'120.8 (2)C1B—C5B—H5B126.2 (3)
C4'—C3'—H3'120.8 (2)Fe—C5B—H5B125.14 (14)
C5'—C4'—C3'122.2 (4)C7—C6—C5122.4 (4)
C5'—C4'—Br119.9 (3)C7—C6—H6118.8 (2)
C3'—C4'—Br117.8 (3)C5—C6—H6118.8 (2)
C4'—C5'—C6'118.7 (4)C6—C7—N8118.8 (4)
C4'—C5'—H5'120.7 (2)C6—C7—C12127.5 (4)
C6'—C5'—H5'120.7 (2)N8—C7—C12113.7 (3)
C5'—C6'—C1'120.6 (4)N1—N8—C7125.0 (3)
C5'—C6'—H6'119.7 (2)N1—N8—C9112.4 (3)
C1'—C6'—H6'119.7 (2)C7—N8—C9122.5 (3)
C9—C3—C2105.6 (3)C3—C9—N8106.0 (3)
C9—C3—H3127.2 (2)C3—C9—C4135.9 (4)
C2—C3—H3127.2 (2)N8—C9—C4118.0 (3)
C5—C4—C9121.0 (4)N11—C10—C4174.0 (5)
C5—C4—C10125.0 (4)C13—C12—C7113.5 (3)
C9—C4—C10114.0 (3)C13—C12—H12A108.9 (3)
C4—C5—C6117.2 (4)C7—C12—H12A108.9 (2)
C4—C5—C1A123.8 (4)C13—C12—H12B108.9 (2)
C6—C5—C1A119.0 (4)C7—C12—H12B108.9 (2)
C5A—C1A—C2A106.7 (3)H12A—C12—H12B107.7
C5A—C1A—C5125.8 (4)N14—C13—C12175.9 (5)
N8—N1—C2—C30.3 (5)C5B—Fe—C5A—C1A122.9 (3)
N8—N1—C2—C1'179.5 (4)C4B—Fe—C5A—C1A163.5 (2)
N1—C2—C1'—C2'160.5 (4)C2B—Fe—C5A—C1A51.3 (6)
C3—C2—C1'—C2'20.4 (6)C2A—Fe—C5A—C1A38.6 (2)
N1—C2—C1'—C6'17.8 (6)C1B—Fe—C5A—C1A81.3 (3)
C3—C2—C1'—C6'161.3 (4)C4A—Fe—C5A—C1A119.8 (4)
C6'—C1'—C2'—C3'0.2 (6)C3B—Fe—C5A—C1A168.0 (6)
C2—C1'—C2'—C3'178.2 (4)C3A—Fe—C5A—C1A82.4 (3)
C1'—C2'—C3'—C4'0.7 (7)C5B—Fe—C1B—C2B119.5 (4)
C2'—C3'—C4'—C5'1.3 (7)C4B—Fe—C1B—C2B81.3 (3)
C2'—C3'—C4'—Br178.0 (3)C1A—Fe—C1B—C2B119.0 (3)
C3'—C4'—C5'—C6'1.0 (7)C5A—Fe—C1B—C2B161.8 (3)
Br—C4'—C5'—C6'178.4 (3)C2A—Fe—C1B—C2B77.3 (4)
C4'—C5'—C6'—C1'0.0 (7)C4A—Fe—C1B—C2B164.6 (4)
C2'—C1'—C6'—C5'0.5 (6)C3B—Fe—C1B—C2B37.6 (3)
C2—C1'—C6'—C5'177.8 (4)C3A—Fe—C1B—C2B46.0 (8)
N1—C2—C3—C90.0 (5)C4B—Fe—C1B—C5B38.2 (3)
C1'—C2—C3—C9179.2 (4)C2B—Fe—C1B—C5B119.5 (4)
C9—C4—C5—C61.4 (6)C1A—Fe—C1B—C5B121.5 (3)
C10—C4—C5—C6177.7 (4)C5A—Fe—C1B—C5B78.7 (3)
C9—C4—C5—C1A177.8 (4)C2A—Fe—C1B—C5B163.2 (3)
C10—C4—C5—C1A3.1 (7)C4A—Fe—C1B—C5B45.2 (6)
C4—C5—C1A—C5A160.1 (4)C3B—Fe—C1B—C5B81.9 (3)
C6—C5—C1A—C5A20.6 (6)C3A—Fe—C1B—C5B165.5 (6)
C4—C5—C1A—C2A21.8 (7)C5B—C1B—C2B—C3B0.7 (6)
C6—C5—C1A—C2A157.4 (4)Fe—C1B—C2B—C3B59.5 (4)
C4—C5—C1A—Fe69.8 (5)C5B—C1B—C2B—Fe58.8 (3)
C6—C5—C1A—Fe110.9 (4)C5B—Fe—C2B—C3B81.7 (3)
C5B—Fe—C1A—C5A74.9 (3)C4B—Fe—C2B—C3B37.7 (3)
C4B—Fe—C1A—C5A44.5 (6)C1A—Fe—C2B—C3B161.7 (3)
C2B—Fe—C1A—C5A158.3 (3)C5A—Fe—C2B—C3B161.3 (4)
C2A—Fe—C1A—C5A118.2 (3)C2A—Fe—C2B—C3B117.7 (3)
C1B—Fe—C1A—C5A116.6 (3)C1B—Fe—C2B—C3B119.4 (5)
C4A—Fe—C1A—C5A37.2 (2)C4A—Fe—C2B—C3B38.5 (8)
C3B—Fe—C1A—C5A169.7 (5)C3A—Fe—C2B—C3B75.7 (4)
C3A—Fe—C1A—C5A80.7 (3)C5B—Fe—C2B—C1B37.7 (3)
C5B—Fe—C1A—C2A166.8 (3)C4B—Fe—C2B—C1B81.6 (3)
C4B—Fe—C1A—C2A162.7 (5)C1A—Fe—C2B—C1B78.9 (3)
C2B—Fe—C1A—C2A83.5 (3)C5A—Fe—C2B—C1B41.9 (6)
C5A—Fe—C1A—C2A118.2 (3)C2A—Fe—C2B—C1B122.9 (3)
C1B—Fe—C1A—C2A125.2 (3)C4A—Fe—C2B—C1B157.9 (6)
C4A—Fe—C1A—C2A81.0 (3)C3B—Fe—C2B—C1B119.4 (5)
C3B—Fe—C1A—C2A51.5 (6)C3A—Fe—C2B—C1B164.9 (3)
C3A—Fe—C1A—C2A37.6 (3)C1B—C2B—C3B—C4B0.0 (6)
C5B—Fe—C1A—C544.9 (4)Fe—C2B—C3B—C4B59.3 (4)
C4B—Fe—C1A—C575.3 (7)C1B—C2B—C3B—Fe59.3 (4)
C2B—Fe—C1A—C538.5 (5)C5B—Fe—C3B—C4B37.4 (3)
C5A—Fe—C1A—C5119.8 (5)C2B—Fe—C3B—C4B118.9 (5)
C2A—Fe—C1A—C5122.0 (5)C1A—Fe—C3B—C4B163.0 (4)
C1B—Fe—C1A—C53.2 (4)C5A—Fe—C3B—C4B37.9 (8)
C4A—Fe—C1A—C5157.0 (4)C2A—Fe—C3B—C4B159.3 (3)
C3B—Fe—C1A—C570.4 (7)C1B—Fe—C3B—C4B81.4 (3)
C3A—Fe—C1A—C5159.5 (4)C4A—Fe—C3B—C4B74.2 (4)
C5A—C1A—C2A—C3A0.4 (5)C3A—Fe—C3B—C4B116.3 (3)
C5—C1A—C2A—C3A177.9 (4)C5B—Fe—C3B—C2B81.5 (4)
Fe—C1A—C2A—C3A59.7 (3)C4B—Fe—C3B—C2B118.9 (5)
C5A—C1A—C2A—Fe59.3 (3)C1A—Fe—C3B—C2B44.1 (7)
C5—C1A—C2A—Fe122.3 (4)C5A—Fe—C3B—C2B156.8 (6)
C5B—Fe—C2A—C3A156.5 (6)C2A—Fe—C3B—C2B81.8 (4)
C4B—Fe—C2A—C3A46.1 (6)C1B—Fe—C3B—C2B37.5 (4)
C2B—Fe—C2A—C3A124.6 (3)C4A—Fe—C3B—C2B166.9 (3)
C1A—Fe—C2A—C3A119.2 (4)C3A—Fe—C3B—C2B124.8 (4)
C5A—Fe—C2A—C3A80.8 (3)C2B—C3B—C4B—C5B0.6 (6)
C1B—Fe—C2A—C3A166.6 (3)Fe—C3B—C4B—C5B58.7 (3)
C4A—Fe—C2A—C3A37.1 (3)C2B—C3B—C4B—Fe59.3 (4)
C3B—Fe—C2A—C3A81.7 (3)C5B—Fe—C4B—C3B119.9 (4)
C5B—Fe—C2A—C1A37.3 (7)C2B—Fe—C4B—C3B37.9 (3)
C4B—Fe—C2A—C1A165.2 (4)C1A—Fe—C4B—C3B160.5 (5)
C2B—Fe—C2A—C1A116.2 (3)C5A—Fe—C4B—C3B166.0 (3)
C5A—Fe—C2A—C1A38.4 (2)C2A—Fe—C4B—C3B49.4 (6)
C1B—Fe—C2A—C1A74.2 (3)C1B—Fe—C4B—C3B81.6 (4)
C4A—Fe—C2A—C1A82.1 (3)C4A—Fe—C4B—C3B124.5 (3)
C3B—Fe—C2A—C1A159.1 (3)C3A—Fe—C4B—C3B82.8 (4)
C3A—Fe—C2A—C1A119.2 (4)C2B—Fe—C4B—C5B82.0 (3)
C1A—C2A—C3A—C4A0.7 (5)C1A—Fe—C4B—C5B40.6 (6)
Fe—C2A—C3A—C4A58.7 (3)C5A—Fe—C4B—C5B74.1 (3)
C1A—C2A—C3A—Fe59.3 (3)C2A—Fe—C4B—C5B169.3 (4)
C5B—Fe—C3A—C4A42.5 (6)C1B—Fe—C4B—C5B38.3 (3)
C4B—Fe—C3A—C4A79.3 (3)C4A—Fe—C4B—C5B115.6 (3)
C2B—Fe—C3A—C4A163.9 (3)C3B—Fe—C4B—C5B119.9 (4)
C1A—Fe—C3A—C4A81.9 (3)C3A—Fe—C4B—C5B157.3 (3)
C5A—Fe—C3A—C4A37.5 (3)C3B—C4B—C5B—C1B1.0 (5)
C2A—Fe—C3A—C4A120.1 (4)Fe—C4B—C5B—C1B60.4 (3)
C1B—Fe—C3A—C4A160.6 (6)C3B—C4B—C5B—Fe59.3 (4)
C3B—Fe—C3A—C4A122.1 (3)C2B—C1B—C5B—C4B1.0 (5)
C5B—Fe—C3A—C2A162.6 (4)Fe—C1B—C5B—C4B60.4 (3)
C4B—Fe—C3A—C2A160.6 (3)C2B—C1B—C5B—Fe59.4 (4)
C2B—Fe—C3A—C2A76.0 (3)C2B—Fe—C5B—C4B80.9 (3)
C1A—Fe—C3A—C2A38.2 (3)C1A—Fe—C5B—C4B164.8 (3)
C5A—Fe—C3A—C2A82.5 (3)C5A—Fe—C5B—C4B123.5 (3)
C1B—Fe—C3A—C2A40.5 (8)C2A—Fe—C5B—C4B166.6 (5)
C4A—Fe—C3A—C2A120.1 (4)C1B—Fe—C5B—C4B118.2 (4)
C3B—Fe—C3A—C2A117.8 (3)C4A—Fe—C5B—C4B81.9 (3)
C2A—C3A—C4A—C5A0.6 (5)C3B—Fe—C5B—C4B37.2 (3)
Fe—C3A—C4A—C5A59.1 (3)C3A—Fe—C5B—C4B51.8 (6)
C2A—C3A—C4A—Fe58.5 (3)C4B—Fe—C5B—C1B118.2 (4)
C5B—Fe—C4A—C5A79.4 (3)C2B—Fe—C5B—C1B37.4 (3)
C4B—Fe—C4A—C5A121.8 (3)C1A—Fe—C5B—C1B77.0 (3)
C2B—Fe—C4A—C5A167.9 (6)C5A—Fe—C5B—C1B118.2 (3)
C1A—Fe—C4A—C5A37.7 (2)C2A—Fe—C5B—C1B48.4 (7)
C2A—Fe—C4A—C5A82.3 (3)C4A—Fe—C5B—C1B159.8 (3)
C1B—Fe—C4A—C5A47.3 (5)C3B—Fe—C5B—C1B81.1 (3)
C3B—Fe—C4A—C5A162.5 (3)C3A—Fe—C5B—C1B170.0 (4)
C3A—Fe—C4A—C5A119.5 (4)C4—C5—C6—C71.3 (6)
C5B—Fe—C4A—C3A161.1 (3)C1A—C5—C6—C7177.9 (4)
C4B—Fe—C4A—C3A118.6 (3)C5—C6—C7—N80.2 (6)
C2B—Fe—C4A—C3A48.3 (8)C5—C6—C7—C12178.5 (4)
C1A—Fe—C4A—C3A81.8 (3)C2—N1—N8—C7176.9 (4)
C5A—Fe—C4A—C3A119.5 (4)C2—N1—N8—C90.4 (4)
C2A—Fe—C4A—C3A37.3 (3)C6—C7—N8—N1178.0 (4)
C1B—Fe—C4A—C3A166.8 (4)C12—C7—N8—N10.9 (6)
C3B—Fe—C4A—C3A77.9 (3)C6—C7—N8—C91.8 (6)
C3A—C4A—C5A—C1A0.4 (5)C12—C7—N8—C9177.1 (4)
Fe—C4A—C5A—C1A59.1 (3)C2—C3—C9—N80.3 (4)
C3A—C4A—C5A—Fe59.5 (3)C2—C3—C9—C4178.2 (5)
C2A—C1A—C5A—C4A0.0 (5)N1—N8—C9—C30.5 (4)
C5—C1A—C5A—C4A178.4 (4)C7—N8—C9—C3177.1 (4)
Fe—C1A—C5A—C4A59.3 (3)N1—N8—C9—C4178.3 (3)
C2A—C1A—C5A—Fe59.3 (3)C7—N8—C9—C41.7 (6)
C5—C1A—C5A—Fe122.3 (4)C5—C4—C9—C3178.3 (5)
C5B—Fe—C5A—C4A117.3 (3)C10—C4—C9—C30.9 (7)
C4B—Fe—C5A—C4A76.7 (3)C5—C4—C9—N80.1 (6)
C2B—Fe—C5A—C4A171.1 (5)C10—C4—C9—N8179.2 (4)
C1A—Fe—C5A—C4A119.8 (4)C5—C4—C10—N11177 (5)
C2A—Fe—C5A—C4A81.2 (3)C9—C4—C10—N112 (5)
C1B—Fe—C5A—C4A158.9 (3)C6—C7—C12—C137.2 (6)
C3B—Fe—C5A—C4A48.2 (7)N8—C7—C12—C13171.6 (4)
C3A—Fe—C5A—C4A37.4 (3)C7—C12—C13—N14161 (8)

Experimental details

Crystal data
Chemical formula[Fe(C5H5)(C21H12BrN4)]
Mr521.20
Crystal system, space groupTriclinic, P1
Temperature (K)150
a, b, c (Å)7.9608 (1), 10.6844 (1), 12.8215 (3)
α, β, γ (°)93.577 (1), 97.737 (1), 99.046 (1)
V3)1063.28 (3)
Z2
Radiation typeMo Kα
µ (mm1)2.61
Crystal size (mm)0.25 × 0.15 × 0.06
Data collection
DiffractometerBruker SMARTCCD
diffractometer
Absorption correctionψ scan
(XPREP; Sheldrick, 1994)
Tmin, Tmax0.606, 0.855
No. of measured, independent and
observed [I > 2σ(I)] reflections
7790, 4823, 3953
Rint0.040
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.140, 1.03
No. of reflections4783
No. of parameters289
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.46, 0.36

Computer programs: SMART (Bruker, 1998), SMART, SAINT (Bruker, 1998), SHELXS86 (Sheldrick, 1990), SHELXL93 (Sheldrick, 1993), NRCVAX (Gabe et al., 1989), SHELXL93.

Selected bond lengths (Å) top
Fe—C5B2.031 (5)Fe—C2A2.050 (4)
Fe—C4B2.045 (4)Fe—C1B2.044 (5)
Fe—C2B2.049 (5)Fe—C4A2.055 (4)
Fe—C1A2.054 (4)Fe—C3B2.054 (5)
Fe—C5A2.048 (4)Fe—C3A2.062 (5)
 

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