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Mol­ecules of the title compound, [Fe(C5H5)(C11H9N2O)], form (101) alternating sheets of the pyridylamide and ferrocene groups via amide to pyridine N—H...N hydrogen-bonding inter­actions and cyclo­penta­dienyl to pyridine C—H...π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806031084/hg2092sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806031084/hg2092Isup2.hkl
Contains datablock I

CCDC reference: 621352

Key indicators

  • Single-crystal X-ray study
  • T = 85 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.019
  • wR factor = 0.047
  • Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR) is > 1.10 Tmin and Tmax reported: 0.775 0.827 Tmin and Tmax expected: 0.740 0.869 RR = 1.101 Please check that your absorption correction is appropriate. PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 1.05 PLAT141_ALERT_4_C su on a - Axis Small or Missing (x 100000) ..... 10 Ang. PLAT142_ALERT_4_C su on b - Axis Small or Missing (x 100000) ..... 10 Ang.
Alert level G ABSTM02_ALERT_3_G 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 1.051 Tmax scaled 0.869 Tmin scaled 0.815 REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 26.37 From the CIF: _reflns_number_total 2581 Count of symmetry unique reflns 1395 Completeness (_total/calc) 185.02% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1186 Fraction of Friedel pairs measured 0.850 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Siemens, 1995); cell refinement: SMART; data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Mercury (Version 1.4.1; Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999).

(4-Pyridylaminocarbonyl)ferrocene top
Crystal data top
[Fe(C5H5)(C11H9N2O)]Dx = 1.583 Mg m3
Mr = 306.14Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca21Cell parameters from 8192 reflections
a = 10.5859 (1) Åθ = 1.6–26.4°
b = 12.6355 (1) ŵ = 1.17 mm1
c = 9.6041 (1) ÅT = 85 K
V = 1284.63 (2) Å3Plate, orange
Z = 40.28 × 0.22 × 0.12 mm
F(000) = 632
Data collection top
Siemens SMART CCD
diffractometer
2581 independent reflections
Radiation source: fine-focus sealed tube2471 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
ω scansθmax = 26.4°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1313
Tmin = 0.775, Tmax = 0.827k = 1515
11891 measured reflectionsl = 1111
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.019H-atom parameters constrained
wR(F2) = 0.047 w = 1/[σ2(Fo2) + (0.0225P)2 + 0.372P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
2581 reflectionsΔρmax = 0.26 e Å3
181 parametersΔρmin = 0.21 e Å3
1 restraintAbsolute structure: Flack (1983), 1188 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.023 (12)
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*/Ueq
Fe10.463957 (18)0.343269 (15)0.36538 (3)0.01272 (7)
C40.62594 (14)0.43244 (11)0.3684 (3)0.0170 (3)
H40.67910.44570.29330.020*
C50.63574 (16)0.34538 (13)0.46385 (19)0.0154 (3)
C90.33799 (14)0.22030 (12)0.3624 (3)0.0177 (3)
H90.31590.17820.43810.021*
C140.87401 (15)0.05945 (13)0.68432 (19)0.0148 (3)
H140.85580.10870.75340.018*
C20.46498 (16)0.44726 (14)0.5291 (2)0.0181 (4)
H20.39480.47240.57710.022*
C30.51980 (17)0.49511 (14)0.40936 (19)0.0189 (4)
H30.49160.55630.36550.023*
C100.27728 (16)0.31615 (14)0.32164 (19)0.0191 (4)
H100.20850.34730.36570.023*
C80.43834 (16)0.20034 (14)0.2671 (2)0.0178 (4)
H80.49300.14270.26950.021*
O10.82610 (10)0.27651 (9)0.37100 (19)0.0233 (3)
N10.98275 (13)0.07113 (12)0.61244 (16)0.0160 (3)
N20.72474 (13)0.17807 (11)0.53795 (16)0.0153 (3)
H2A0.65620.17420.58570.018*
C130.78782 (15)0.02137 (14)0.66159 (18)0.0153 (3)
H130.71500.02600.71540.018*
C10.53520 (16)0.35447 (14)0.5634 (2)0.0161 (4)
H10.51880.30840.63670.019*
C120.81157 (16)0.09614 (14)0.55662 (18)0.0137 (3)
C110.73691 (16)0.26463 (13)0.45113 (18)0.0148 (3)
C151.00192 (17)0.00008 (15)0.51100 (19)0.0152 (3)
H151.07560.00650.45900.018*
C160.92109 (16)0.08296 (14)0.47675 (19)0.0145 (3)
H160.93930.12820.40310.017*
C60.34099 (17)0.35592 (14)0.2009 (2)0.0191 (4)
H60.32110.41760.15290.023*
C70.44046 (17)0.28394 (14)0.16752 (19)0.0193 (4)
H70.49680.29050.09370.023*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.01237 (10)0.01277 (11)0.01302 (11)0.00078 (8)0.00028 (12)0.00064 (13)
C40.0170 (7)0.0149 (7)0.0191 (8)0.0026 (5)0.0011 (10)0.0024 (10)
C50.0145 (8)0.0161 (8)0.0156 (9)0.0027 (6)0.0037 (7)0.0002 (7)
C90.0169 (7)0.0168 (7)0.0194 (8)0.0036 (6)0.0028 (9)0.0019 (10)
C140.0148 (8)0.0148 (8)0.0148 (9)0.0022 (6)0.0006 (7)0.0009 (7)
C20.0190 (9)0.0173 (9)0.0180 (9)0.0005 (7)0.0012 (7)0.0074 (7)
C30.0211 (9)0.0121 (8)0.0236 (10)0.0010 (7)0.0049 (7)0.0003 (6)
C100.0132 (8)0.0214 (9)0.0226 (10)0.0002 (7)0.0033 (6)0.0027 (7)
C80.0194 (8)0.0147 (8)0.0192 (9)0.0019 (7)0.0041 (7)0.0041 (7)
O10.0165 (5)0.0258 (6)0.0276 (7)0.0025 (4)0.0057 (7)0.0110 (8)
N10.0153 (7)0.0156 (7)0.0172 (8)0.0000 (6)0.0012 (6)0.0014 (6)
N20.0112 (7)0.0168 (7)0.0180 (8)0.0012 (5)0.0022 (6)0.0027 (6)
C130.0118 (7)0.0195 (9)0.0146 (9)0.0009 (6)0.0007 (6)0.0006 (7)
C10.0169 (8)0.0170 (9)0.0144 (9)0.0017 (7)0.0019 (7)0.0017 (7)
C120.0125 (8)0.0141 (8)0.0145 (9)0.0015 (6)0.0034 (6)0.0002 (7)
C110.0140 (8)0.0162 (8)0.0141 (9)0.0030 (7)0.0028 (6)0.0001 (7)
C150.0116 (7)0.0187 (8)0.0154 (8)0.0003 (6)0.0015 (6)0.0031 (7)
C160.0134 (8)0.0161 (8)0.0139 (8)0.0018 (7)0.0016 (7)0.0003 (7)
C60.0194 (8)0.0207 (9)0.0171 (10)0.0019 (7)0.0044 (7)0.0012 (8)
C70.0219 (9)0.0202 (9)0.0157 (9)0.0007 (7)0.0019 (7)0.0040 (7)
Geometric parameters (Å, º) top
Fe1—C12.0504 (18)N2—C111.381 (2)
Fe1—C22.0490 (18)N2—C121.396 (2)
Fe1—C32.0515 (18)C13—C121.404 (2)
Fe1—C42.0520 (14)C14—C131.387 (2)
Fe1—C52.0498 (17)C14—N11.350 (2)
Fe1—C62.0531 (18)N1—C151.342 (2)
Fe1—C72.0579 (18)C15—C161.392 (3)
Fe1—C82.0556 (18)C12—C161.400 (2)
Fe1—C92.0477 (15)C4—H40.9300
Fe1—C102.0492 (17)C9—H90.9300
C2—C11.427 (2)C14—H140.9300
C2—C31.423 (3)C2—H20.9300
C4—C31.430 (2)C3—H30.9300
C4—C51.436 (3)C10—H100.9300
C5—C11.435 (3)C8—H80.9300
C6—C71.428 (3)N2—H2A0.8600
C8—C71.425 (3)C13—H130.9300
C9—C81.425 (3)C1—H10.9300
C9—C101.426 (2)C15—H150.9300
C10—C61.432 (3)C16—H160.9300
C5—C111.484 (2)C6—H60.9300
O1—C111.227 (2)C7—H70.9300
C9—Fe1—C2120.04 (8)N1—C14—H14117.9
C9—Fe1—C1040.74 (7)C13—C14—H14117.9
C2—Fe1—C10105.64 (7)C3—C2—C1108.85 (16)
C9—Fe1—C5126.44 (7)C3—C2—Fe169.79 (10)
C2—Fe1—C568.47 (7)C1—C2—Fe169.68 (10)
C10—Fe1—C5162.23 (7)C3—C2—H2125.6
C9—Fe1—C1107.74 (9)C1—C2—H2125.6
C2—Fe1—C140.74 (7)Fe1—C2—H2126.5
C10—Fe1—C1123.81 (7)C2—C3—C4107.92 (17)
C5—Fe1—C140.97 (7)C2—C3—Fe169.60 (10)
C9—Fe1—C3154.17 (7)C4—C3—Fe169.62 (9)
C2—Fe1—C340.60 (7)C2—C3—H3126.0
C10—Fe1—C3118.45 (7)C4—C3—H3126.0
C5—Fe1—C368.73 (7)Fe1—C3—H3126.3
C1—Fe1—C368.81 (7)C9—C10—C6107.95 (17)
C9—Fe1—C4163.95 (6)C9—C10—Fe169.58 (9)
C2—Fe1—C468.45 (8)C6—C10—Fe169.71 (10)
C10—Fe1—C4154.23 (7)C9—C10—H10126.0
C5—Fe1—C440.98 (7)C6—C10—H10126.0
C1—Fe1—C469.01 (9)Fe1—C10—H10126.3
C3—Fe1—C440.79 (7)C9—C8—C7108.17 (16)
C9—Fe1—C668.63 (8)C9—C8—Fe169.38 (10)
C2—Fe1—C6122.94 (7)C7—C8—Fe169.81 (10)
C10—Fe1—C640.87 (7)C9—C8—H8125.9
C5—Fe1—C6156.40 (8)C7—C8—H8125.9
C1—Fe1—C6160.27 (7)Fe1—C8—H8126.5
C3—Fe1—C6105.56 (7)C15—N1—C14115.27 (15)
C4—Fe1—C6119.86 (8)C11—N2—C12127.10 (14)
C9—Fe1—C840.63 (8)C11—N2—H2A116.4
C2—Fe1—C8156.40 (8)C12—N2—H2A116.4
C10—Fe1—C868.39 (7)C14—C13—C12119.38 (16)
C5—Fe1—C8109.89 (7)C14—C13—H13120.3
C1—Fe1—C8122.34 (7)C12—C13—H13120.3
C3—Fe1—C8162.58 (8)C2—C1—C5107.37 (16)
C4—Fe1—C8126.80 (8)C2—C1—Fe169.58 (10)
C6—Fe1—C868.38 (7)C5—C1—Fe169.49 (10)
C9—Fe1—C768.42 (9)C2—C1—H1126.3
C2—Fe1—C7160.52 (7)C5—C1—H1126.3
C10—Fe1—C768.48 (7)Fe1—C1—H1126.2
C5—Fe1—C7122.54 (7)N2—C12—C16124.27 (16)
C1—Fe1—C7157.80 (7)N2—C12—C13118.24 (16)
C3—Fe1—C7124.45 (7)C16—C12—C13117.49 (16)
C4—Fe1—C7108.30 (9)O1—C11—N2123.17 (15)
C6—Fe1—C740.65 (7)O1—C11—C5121.51 (15)
C8—Fe1—C740.54 (7)N2—C11—C5115.29 (15)
C3—C4—C5107.77 (18)N1—C15—C16125.68 (17)
C3—C4—Fe169.59 (9)N1—C15—H15117.2
C5—C4—Fe169.43 (9)C16—C15—H15117.2
C3—C4—H4126.1C15—C16—C12117.97 (16)
C5—C4—H4126.1C15—C16—H16121.0
Fe1—C4—H4126.4C12—C16—H16121.0
C1—C5—C4108.08 (15)C7—C6—C10107.79 (16)
C1—C5—C11130.17 (16)C7—C6—Fe169.85 (10)
C4—C5—C11121.75 (17)C10—C6—Fe169.41 (10)
C1—C5—Fe169.53 (10)C7—C6—H6126.1
C4—C5—Fe169.59 (9)C10—C6—H6126.1
C11—C5—Fe1126.39 (12)Fe1—C6—H6126.2
C8—C9—C10108.05 (19)C8—C7—C6108.04 (16)
C8—C9—Fe169.98 (10)C8—C7—Fe169.64 (10)
C10—C9—Fe169.69 (9)C6—C7—Fe169.49 (10)
C8—C9—H9126.0C8—C7—H7126.0
C10—C9—H9126.0C6—C7—H7126.0
Fe1—C9—H9125.9Fe1—C7—H7126.5
N1—C14—C13124.12 (16)
 

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