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The cation of the title compound, [Fe(C5H5)(C8H13N)]NO3, forms a bifurcated N—H...O hydrogen bond to the nitrate anion.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806017867/bi2009sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806017867/bi2009Isup2.hkl
Contains datablock I

CCDC reference: 610696

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.010 Å
  • R factor = 0.067
  • wR factor = 0.163
  • Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C8 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Fe1 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N2 PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 10
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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

Computing details top

Data collection: TEXRAY (Molecular Structure Corporation, 1999); cell refinement: TEXRAY; data reduction: TEXSAN (Molecular Structure Corporation, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEX (McArdle, 1995); software used to prepare material for publication: SHELXL97.

(N-Ferrocenylmethyl)dimethylammonium nitrate top
Crystal data top
[Fe(C5H5)(C8H13N)]NO3F(000) = 640
Mr = 306.14Dx = 1.471 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4120 reflections
a = 17.4375 (14) Åθ = 2.4–25.1°
b = 7.4054 (5) ŵ = 1.10 mm1
c = 11.0348 (9) ÅT = 293 K
β = 104.049 (2)°Block, brown
V = 1382.32 (18) Å30.31 × 0.25 × 0.18 mm
Z = 4
Data collection top
Rigaku Weissenberg IP
diffractometer
2445 independent reflections
Radiation source: fine-focus sealed tube1886 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
ω scansθmax = 25.1°, θmin = 2.4°
Absorption correction: ψ scan
(TEXRAY; Molecular Structure Corporation, 1999)
h = 2014
Tmin = 0.727, Tmax = 0.821k = 86
4660 measured reflectionsl = 813
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)] = 0.067Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.163H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0446P)2 + 6.2892P]
where P = (Fo2 + 2Fc2)/3
2406 reflections(Δ/σ)max < 0.001
173 parametersΔρmax = 0.36 e Å3
0 restraintsΔρmin = 0.43 e Å3
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
Fe10.35579 (5)0.52379 (10)0.30504 (7)0.0378 (3)
O10.0973 (4)0.7562 (9)0.5980 (7)0.118 (3)
O20.1167 (4)0.4799 (8)0.5513 (5)0.0933 (19)
O30.1241 (3)0.6883 (7)0.4251 (5)0.0756 (15)
N20.1118 (3)0.6436 (8)0.5255 (6)0.0573 (14)
N10.1262 (3)0.3027 (6)0.3241 (4)0.0443 (12)
H1N0.11950.39490.38450.07 (2)*
C10.2691 (3)0.3604 (7)0.3361 (5)0.0389 (13)
H1A0.42830.84630.37230.088*
C20.2975 (3)0.4756 (8)0.4410 (5)0.0439 (14)
H2A0.28220.84840.25860.087*
C30.3796 (4)0.4413 (9)0.4871 (5)0.0518 (16)
H3A0.26080.62640.08210.084*
C40.4020 (4)0.3068 (9)0.4112 (6)0.0538 (17)
H4A0.39460.48350.08170.094*
C50.3336 (4)0.2554 (7)0.3189 (6)0.0468 (15)
H5A0.49730.62050.26260.089*
C60.4033 (5)0.7719 (10)0.3000 (7)0.074 (2)
C70.4408 (4)0.6496 (12)0.2397 (8)0.074 (2)
H7A0.26610.56320.47490.053*
C80.3847 (6)0.5739 (10)0.1409 (7)0.078 (3)
H8A0.41490.50210.55800.062*
C90.3114 (5)0.6526 (10)0.1412 (7)0.070 (2)
H9A0.45530.25760.42070.065*
C100.3232 (5)0.7735 (9)0.2367 (8)0.073 (2)
H10A0.33160.16480.25350.056*
C110.1868 (3)0.3616 (8)0.2546 (5)0.0430 (14)
H11A0.18430.28150.18430.052*
H11B0.17400.48250.22210.052*
C120.1405 (4)0.1185 (9)0.3758 (6)0.0615 (18)
H12A0.19250.11210.43030.092*
H12B0.13630.03360.30880.092*
H12C0.10190.09020.42200.092*
C130.0447 (4)0.3187 (10)0.2400 (7)0.0622 (18)
H13A0.00630.28290.28470.093*
H13B0.04050.24190.16860.093*
H13C0.03520.44160.21290.093*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0398 (5)0.0324 (4)0.0421 (5)0.0005 (4)0.0115 (3)0.0024 (4)
O10.133 (6)0.106 (5)0.143 (6)0.037 (4)0.087 (5)0.077 (5)
O20.142 (6)0.064 (4)0.079 (4)0.005 (4)0.035 (4)0.015 (3)
O30.090 (4)0.070 (3)0.071 (3)0.017 (3)0.027 (3)0.018 (3)
N10.049 (3)0.039 (3)0.045 (3)0.006 (2)0.013 (2)0.004 (2)
N20.053 (3)0.057 (4)0.065 (4)0.004 (3)0.020 (3)0.006 (3)
C10.041 (3)0.035 (3)0.043 (3)0.004 (2)0.013 (3)0.004 (2)
C20.042 (3)0.053 (4)0.040 (3)0.003 (3)0.017 (2)0.001 (3)
C30.056 (4)0.060 (4)0.035 (3)0.010 (3)0.004 (3)0.005 (3)
C40.045 (4)0.047 (4)0.069 (4)0.004 (3)0.015 (3)0.024 (3)
C50.056 (4)0.028 (3)0.062 (4)0.000 (3)0.025 (3)0.003 (3)
C60.099 (6)0.045 (4)0.071 (5)0.034 (4)0.011 (5)0.002 (4)
C70.050 (4)0.093 (6)0.082 (6)0.005 (4)0.020 (4)0.043 (5)
C80.137 (8)0.056 (5)0.057 (5)0.002 (5)0.054 (5)0.009 (4)
C90.073 (5)0.055 (5)0.070 (5)0.020 (4)0.004 (4)0.026 (4)
C100.080 (6)0.038 (4)0.108 (6)0.009 (4)0.038 (5)0.023 (4)
C110.044 (3)0.039 (3)0.046 (3)0.006 (3)0.009 (3)0.004 (3)
C120.064 (4)0.059 (4)0.064 (4)0.007 (3)0.019 (4)0.021 (3)
C130.039 (4)0.067 (4)0.078 (5)0.002 (3)0.009 (3)0.008 (4)
Geometric parameters (Å, º) top
Fe1—C12.029 (5)C11—H11A0.970
Fe1—C22.038 (5)C11—H11B0.970
Fe1—C32.043 (6)C6—C71.379 (11)
Fe1—C42.036 (6)C6—C101.402 (11)
Fe1—C52.037 (6)C6—H1A0.980
Fe1—C62.022 (7)C3—H8A0.980
Fe1—C72.025 (7)C13—H13A0.960
Fe1—C82.028 (7)C13—H13B0.960
Fe1—C92.024 (7)C13—H13C0.960
Fe1—C102.025 (7)C7—C81.393 (11)
N1—C121.476 (8)C7—H5A0.980
N1—C131.502 (8)C12—H12A0.960
N1—C111.513 (7)C12—H12B0.960
N1—H1N0.980C12—H12C0.960
C5—C11.418 (8)C8—C91.405 (11)
C5—C41.418 (9)C8—H4A0.980
C5—H10A0.980C10—C91.360 (11)
C2—C31.421 (8)C10—H2A0.980
C2—C11.427 (8)C9—H3A0.980
C2—H7A0.980N2—O11.223 (7)
C1—C111.497 (8)N2—O31.225 (7)
C4—C31.416 (9)N2—O21.243 (7)
C4—H9A0.980
C6—Fe1—C967.5 (3)C5—C1—Fe169.9 (3)
C6—Fe1—C1040.5 (3)C2—C1—Fe169.8 (3)
C9—Fe1—C1039.3 (3)C11—C1—Fe1122.7 (4)
C6—Fe1—C739.8 (3)C3—C4—C5108.0 (6)
C9—Fe1—C767.7 (3)C3—C4—Fe170.0 (3)
C10—Fe1—C767.1 (3)C5—C4—Fe169.7 (3)
C6—Fe1—C867.5 (3)C3—C4—H9A126.0
C9—Fe1—C840.6 (3)C5—C4—H9A126.0
C10—Fe1—C867.0 (3)Fe1—C4—H9A126.0
C7—Fe1—C840.2 (3)C1—C11—N1112.3 (4)
C6—Fe1—C1150.9 (3)C1—C11—H11A109.1
C9—Fe1—C1107.0 (3)N1—C11—H11A109.1
C10—Fe1—C1117.0 (3)C1—C11—H11B109.1
C7—Fe1—C1166.8 (3)N1—C11—H11B109.1
C8—Fe1—C1128.1 (3)H11A—C11—H11B107.9
C6—Fe1—C4128.7 (3)C7—C6—C10107.2 (7)
C9—Fe1—C4153.9 (3)C7—C6—Fe170.2 (4)
C10—Fe1—C4166.1 (3)C10—C6—Fe169.9 (4)
C7—Fe1—C4110.3 (3)C7—C6—H1A126.4
C8—Fe1—C4120.6 (3)C10—C6—H1A126.4
C1—Fe1—C468.8 (2)Fe1—C6—H1A126.4
C6—Fe1—C5167.1 (3)C4—C3—C2108.2 (5)
C9—Fe1—C5119.2 (3)C4—C3—Fe169.4 (3)
C10—Fe1—C5151.3 (3)C2—C3—Fe169.4 (3)
C7—Fe1—C5130.1 (3)C4—C3—H8A125.9
C8—Fe1—C5109.8 (3)C2—C3—H8A125.9
C1—Fe1—C540.8 (2)Fe1—C3—H8A125.9
C4—Fe1—C540.8 (2)N1—C13—H13A109.5
C6—Fe1—C2117.4 (3)N1—C13—H13B109.5
C9—Fe1—C2126.1 (3)H13A—C13—H13B109.5
C10—Fe1—C2106.8 (3)N1—C13—H13C109.5
C7—Fe1—C2151.8 (3)H13A—C13—H13C109.5
C8—Fe1—C2165.0 (3)H13B—C13—H13C109.5
C1—Fe1—C241.1 (2)C6—C7—C8108.5 (7)
C4—Fe1—C268.7 (2)C6—C7—Fe170.0 (4)
C5—Fe1—C268.7 (2)C8—C7—Fe170.0 (4)
C6—Fe1—C3108.2 (3)C6—C7—H5A125.8
C9—Fe1—C3164.0 (3)C8—C7—H5A125.8
C10—Fe1—C3127.6 (3)Fe1—C7—H5A125.8
C7—Fe1—C3119.7 (3)N1—C12—H12A109.5
C8—Fe1—C3153.8 (3)N1—C12—H12B109.5
C1—Fe1—C368.8 (2)H12A—C12—H12B109.5
C4—Fe1—C340.6 (3)N1—C12—H12C109.5
C5—Fe1—C368.4 (3)H12A—C12—H12C109.5
C2—Fe1—C340.8 (2)H12B—C12—H12C109.5
C12—N1—C13110.9 (5)C7—C8—C9107.3 (7)
C12—N1—C11112.9 (5)C7—C8—Fe169.8 (4)
C13—N1—C11109.7 (5)C9—C8—Fe169.6 (4)
C12—N1—H1N114.7C7—C8—H4A126.3
C13—N1—H1N96.5C9—C8—H4A126.3
C11—N1—H1N110.9Fe1—C8—H4A126.3
C1—C5—C4108.2 (5)C9—C10—C6109.0 (7)
C1—C5—Fe169.3 (3)C9—C10—Fe170.3 (4)
C4—C5—Fe169.6 (3)C6—C10—Fe169.6 (4)
C1—C5—H10A125.9C9—C10—H2A125.5
C4—C5—H10A125.9C6—C10—H2A125.5
Fe1—C5—H10A125.9Fe1—C10—H2A125.5
C3—C2—C1107.7 (5)C10—C9—C8107.9 (7)
C3—C2—Fe169.8 (3)C10—C9—Fe170.4 (4)
C1—C2—Fe169.1 (3)C8—C9—Fe169.9 (4)
C3—C2—H7A126.1C10—C9—H3A126.0
C1—C2—H7A126.1C8—C9—H3A126.0
Fe1—C2—H7A126.1Fe1—C9—H3A126.0
C5—C1—C2107.8 (5)O1—N2—O3121.1 (7)
C5—C1—C11126.8 (5)O1—N2—O2121.9 (7)
C2—C1—C11125.2 (5)O3—N2—O2116.9 (6)
C6—Fe1—C5—C1158.8 (12)C3—Fe1—C1—C581.1 (4)
C9—Fe1—C5—C182.2 (5)C6—Fe1—C1—C251.7 (7)
C10—Fe1—C5—C148.0 (7)C9—Fe1—C1—C2125.9 (4)
C7—Fe1—C5—C1166.6 (4)C10—Fe1—C1—C284.8 (4)
C8—Fe1—C5—C1125.9 (4)C7—Fe1—C1—C2170.1 (11)
C4—Fe1—C5—C1119.9 (5)C8—Fe1—C1—C2165.6 (4)
C2—Fe1—C5—C138.2 (3)C4—Fe1—C1—C281.4 (4)
C3—Fe1—C5—C182.1 (4)C5—Fe1—C1—C2118.8 (5)
C6—Fe1—C5—C439.0 (14)C3—Fe1—C1—C237.7 (4)
C9—Fe1—C5—C4157.9 (4)C6—Fe1—C1—C1168.0 (7)
C10—Fe1—C5—C4167.8 (6)C9—Fe1—C1—C116.3 (6)
C7—Fe1—C5—C473.6 (5)C10—Fe1—C1—C1134.9 (6)
C8—Fe1—C5—C4114.3 (5)C7—Fe1—C1—C1170.3 (13)
C1—Fe1—C5—C4119.9 (5)C8—Fe1—C1—C1146.0 (6)
C2—Fe1—C5—C481.7 (4)C4—Fe1—C1—C11158.9 (5)
C3—Fe1—C5—C437.7 (4)C5—Fe1—C1—C11121.6 (6)
C6—Fe1—C2—C386.3 (5)C2—Fe1—C1—C11119.6 (6)
C9—Fe1—C2—C3167.5 (4)C3—Fe1—C1—C11157.3 (5)
C10—Fe1—C2—C3128.8 (4)C1—C5—C4—C31.1 (7)
C7—Fe1—C2—C356.1 (7)Fe1—C5—C4—C359.7 (4)
C8—Fe1—C2—C3168.1 (10)C1—C5—C4—Fe158.7 (4)
C1—Fe1—C2—C3119.1 (5)C6—Fe1—C4—C371.3 (5)
C4—Fe1—C2—C337.3 (4)C9—Fe1—C4—C3167.2 (6)
C5—Fe1—C2—C381.2 (4)C10—Fe1—C4—C336.0 (13)
C6—Fe1—C2—C1154.5 (4)C7—Fe1—C4—C3112.4 (5)
C9—Fe1—C2—C173.4 (5)C8—Fe1—C4—C3155.7 (4)
C10—Fe1—C2—C1112.1 (4)C1—Fe1—C4—C381.6 (4)
C7—Fe1—C2—C1175.2 (6)C5—Fe1—C4—C3119.1 (5)
C8—Fe1—C2—C149.0 (12)C2—Fe1—C4—C337.4 (4)
C4—Fe1—C2—C181.8 (4)C6—Fe1—C4—C5169.7 (4)
C5—Fe1—C2—C137.9 (3)C9—Fe1—C4—C548.2 (8)
C3—Fe1—C2—C1119.1 (5)C10—Fe1—C4—C5155.1 (11)
C4—C5—C1—C20.9 (6)C7—Fe1—C4—C5128.5 (4)
Fe1—C5—C1—C259.8 (4)C8—Fe1—C4—C585.2 (5)
C4—C5—C1—C11175.2 (5)C1—Fe1—C4—C537.4 (3)
Fe1—C5—C1—C11116.4 (5)C2—Fe1—C4—C581.7 (4)
C4—C5—C1—Fe158.8 (4)C3—Fe1—C4—C5119.1 (5)
C3—C2—C1—C50.4 (6)C5—C1—C11—N1118.8 (6)
Fe1—C2—C1—C559.8 (4)C2—C1—C11—N165.7 (7)
C3—C2—C1—C11175.8 (5)Fe1—C1—C11—N1152.9 (4)
Fe1—C2—C1—C11116.4 (5)C12—N1—C11—C159.5 (6)
C3—C2—C1—Fe159.4 (4)C13—N1—C11—C1176.2 (5)
C6—Fe1—C1—C5170.5 (6)C9—Fe1—C6—C781.6 (5)
C9—Fe1—C1—C5115.3 (4)C10—Fe1—C6—C7117.8 (7)
C10—Fe1—C1—C5156.4 (4)C8—Fe1—C6—C737.5 (5)
C7—Fe1—C1—C551.3 (13)C1—Fe1—C6—C7166.3 (5)
C8—Fe1—C1—C575.6 (5)C4—Fe1—C6—C774.5 (6)
C4—Fe1—C1—C537.4 (4)C3—Fe1—C9—C8158.6 (9)
C2—Fe1—C1—C5118.8 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O20.981.962.870 (8)154
N1—H1N···O30.982.223.068 (7)145
 

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