metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

Dimeth­yl(3-oxo-3-phenyl­prop­yl)aza­nium tetra­chloridoferrate(III)

aCollege of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
*Correspondence e-mail: jinlei8812@163.com

(Received 8 April 2012; accepted 25 April 2012; online 28 April 2012)

In the title mol­ecular salt, (C11H16NO)[FeCl4], an intra­molecular N—H⋯O hydrogen bond in the cation generates an S(6) loop and the conformation of the C(=O)—C—C—N chain is gauche [torsion angle = 57.0 (6)°]. The anion is a near-regular tetra­hedron [range of Cl—Fe—Cl angles = 107.93 (8)–112.13 (10)°]. There are no directional inter-ionic bonds in the crystal.

Related literature

For related structures, see: Hay & Geib (2005[Hay, M. T. & Geib, S. J. (2005). Acta Cryst. E61, m190-m191.]); Ton & Bolte (2004[Ton, C. & Bolte, M. (2004). Acta Cryst. E60, o616-o617.]).

[Scheme 1]

Experimental

Crystal data
  • (C11H16NO)[FeCl4]

  • Mr = 375.90

  • Monoclinic, P 21 /c

  • a = 6.3166 (13) Å

  • b = 15.149 (3) Å

  • c = 17.293 (4) Å

  • β = 92.55 (3)°

  • V = 1653.1 (6) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 1.55 mm−1

  • T = 291 K

  • 0.26 × 0.22 × 0.20 mm

Data collection
  • Rigaku Mercury2 diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.08, Tmax = 0.12

  • 15234 measured reflections

  • 3244 independent reflections

  • 1895 reflections with I > 2σ(I)

  • Rint = 0.080

Refinement
  • R[F2 > 2σ(F2)] = 0.071

  • wR(F2) = 0.172

  • S = 1.11

  • 3244 reflections

  • 164 parameters

  • 61 restraints

  • H-atom parameters constrained

  • Δρmax = 0.80 e Å−3

  • Δρmin = −0.45 e Å−3

Table 1
Selected bond lengths (Å)

Fe1—Cl1 2.164 (2)
Fe1—Cl2 2.1854 (18)
Fe1—Cl3 2.180 (2)
Fe1—Cl4 2.179 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1D⋯O1 0.91 2.06 2.735 (7) 130

Data collection: CrystalClear (Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Related literature top

For related structures, see: Hay & Geib (2005); Ton & Bolte (2004).

Experimental top

At room temperature, dimethyl-(3-oxo-3-phenyl-propyl)-amine (5 mmol, 0.89 g) was dissolved in 30 ml water, then FeCl3.6H2O (5 mmol, 1.35 g) was added slowly with sirring. Orange plates were obtained by the slow evaporation of the above filtrate after a week in air.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids.
Dimethyl(3-oxo-3-phenylpropyl)azanium tetrachloridoferrate(III) top
Crystal data top
(C11H16NO)[FeCl4]Z = 4
Mr = 375.90F(000) = 764
Monoclinic, P21/cDx = 1.510 Mg m3
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 6.3166 (13) Åθ = 3.2–26°
b = 15.149 (3) ŵ = 1.55 mm1
c = 17.293 (4) ÅT = 291 K
β = 92.55 (3)°Block, yellow
V = 1653.1 (6) Å30.26 × 0.22 × 0.20 mm
Data collection top
Rigaku Mercury2
diffractometer
3244 independent reflections
Radiation source: fine-focus sealed tube1895 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.080
Detector resolution: 13.6612 pixels mm-1θmax = 26.0°, θmin = 3.2°
CCD_Profile_fitting scansh = 77
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)
k = 1818
Tmin = 0.08, Tmax = 0.12l = 2121
15234 measured reflections
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)] = 0.071H-atom parameters constrained
wR(F2) = 0.172 w = 1/[σ2(Fo2) + (0.0538P)2 + 2.3762P]
where P = (Fo2 + 2Fc2)/3
S = 1.11(Δ/σ)max < 0.001
3244 reflectionsΔρmax = 0.80 e Å3
164 parametersΔρmin = 0.45 e Å3
61 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0126 (14)
Crystal data top
(C11H16NO)[FeCl4]V = 1653.1 (6) Å3
Mr = 375.90Z = 4
Monoclinic, P21/cMo Kα radiation
a = 6.3166 (13) ŵ = 1.55 mm1
b = 15.149 (3) ÅT = 291 K
c = 17.293 (4) Å0.26 × 0.22 × 0.20 mm
β = 92.55 (3)°
Data collection top
Rigaku Mercury2
diffractometer
3244 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)
1895 reflections with I > 2σ(I)
Tmin = 0.08, Tmax = 0.12Rint = 0.080
15234 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.07161 restraints
wR(F2) = 0.172H-atom parameters constrained
S = 1.11Δρmax = 0.80 e Å3
3244 reflectionsΔρmin = 0.45 e Å3
164 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*/Ueq
C10.0240 (17)0.4076 (6)0.9427 (6)0.135 (3)
H1A0.01420.39600.99740.203*
H1B0.16310.42920.92850.203*
H1C0.07970.45100.93010.203*
C20.0080 (15)0.3420 (6)0.8157 (5)0.120 (3)
H2A0.03470.28780.78900.180*
H2B0.11400.38470.80370.180*
H2C0.12940.36410.79950.180*
C30.1593 (13)0.2645 (5)0.9215 (5)0.102 (2)
H3A0.29430.28790.90200.122*
H3B0.16290.26030.97740.122*
C40.1252 (11)0.1715 (4)0.8870 (4)0.0829 (19)
H4A0.23900.13350.90270.099*
H4B0.13630.17600.83100.099*
C50.0813 (10)0.1284 (4)0.9097 (3)0.0627 (16)
C60.1018 (9)0.0308 (4)0.9021 (3)0.0547 (14)
C70.0662 (11)0.0227 (4)0.8783 (4)0.0745 (19)
H7A0.19850.00190.86630.089*
C80.0368 (14)0.1134 (5)0.8724 (4)0.088 (2)
H8A0.14910.14950.85590.106*
C90.1574 (15)0.1496 (5)0.8908 (4)0.088 (2)
H9A0.17700.21020.88630.105*
C100.3218 (13)0.0976 (5)0.9157 (5)0.087 (2)
H10A0.45280.12250.92920.104*
C110.2933 (10)0.0084 (4)0.9206 (4)0.0701 (18)
H11A0.40710.02690.93710.084*
Cl10.4836 (3)0.50465 (14)0.21112 (15)0.1142 (8)
Cl20.0148 (3)0.38087 (12)0.17367 (12)0.0850 (6)
Cl30.4451 (4)0.3546 (2)0.05173 (13)0.1258 (9)
Cl40.4761 (3)0.26961 (14)0.24300 (13)0.0987 (7)
Fe10.36032 (13)0.37873 (5)0.17073 (5)0.0576 (3)
N10.0153 (9)0.3257 (3)0.9003 (3)0.0745 (14)
H1D0.14320.30260.91590.089*
O10.2302 (8)0.1727 (3)0.9339 (3)0.0893 (16)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.165 (7)0.114 (6)0.123 (6)0.047 (6)0.041 (6)0.034 (5)
C20.120 (6)0.129 (6)0.113 (6)0.022 (5)0.023 (5)0.006 (5)
C30.100 (5)0.096 (4)0.109 (5)0.026 (4)0.006 (4)0.010 (4)
C40.080 (4)0.065 (4)0.102 (4)0.010 (3)0.014 (3)0.003 (3)
C50.074 (4)0.057 (4)0.056 (4)0.002 (3)0.011 (3)0.005 (3)
C60.064 (4)0.055 (4)0.045 (3)0.003 (3)0.003 (3)0.002 (3)
C70.079 (5)0.071 (5)0.072 (5)0.001 (4)0.007 (4)0.005 (4)
C80.103 (6)0.069 (5)0.092 (6)0.020 (5)0.001 (4)0.018 (4)
C90.122 (7)0.061 (4)0.081 (5)0.010 (5)0.011 (5)0.005 (4)
C100.089 (5)0.071 (5)0.100 (6)0.022 (4)0.001 (4)0.002 (4)
C110.072 (4)0.062 (4)0.076 (5)0.005 (3)0.001 (3)0.004 (3)
Cl10.0904 (15)0.0800 (13)0.170 (2)0.0095 (11)0.0163 (14)0.0386 (14)
Cl20.0490 (9)0.0881 (13)0.1176 (16)0.0042 (9)0.0013 (9)0.0156 (11)
Cl30.1048 (16)0.197 (3)0.0762 (14)0.0392 (17)0.0098 (11)0.0246 (15)
Cl40.0720 (12)0.0990 (14)0.1228 (17)0.0033 (11)0.0227 (11)0.0345 (12)
Fe10.0481 (5)0.0582 (6)0.0660 (6)0.0028 (4)0.0023 (4)0.0042 (4)
N10.081 (3)0.061 (3)0.081 (3)0.013 (3)0.011 (3)0.004 (3)
O10.090 (3)0.061 (3)0.113 (4)0.000 (3)0.041 (3)0.003 (3)
Geometric parameters (Å, º) top
C1—N11.468 (9)C6—C111.372 (8)
C1—H1A0.9600C6—C71.383 (8)
C1—H1B0.9600C7—C81.391 (9)
C1—H1C0.9600C7—H7A0.9300
C2—N11.483 (10)C8—C91.368 (11)
C2—H2A0.9600C8—H8A0.9300
C2—H2B0.9600C9—C101.358 (10)
C2—H2C0.9600C9—H9A0.9300
C3—N11.499 (9)C10—C111.367 (9)
C3—C41.548 (10)C10—H10A0.9300
C3—H3A0.9700C11—H11A0.9300
C3—H3B0.9700Fe1—Cl12.164 (2)
C4—C51.495 (8)Fe1—Cl22.1854 (18)
C4—H4A0.9700Fe1—Cl32.180 (2)
C4—H4B0.9700Fe1—Cl42.179 (2)
C5—O11.214 (7)N1—H1D0.9100
C5—C61.492 (8)
N1—C1—H1A109.5C7—C6—C5122.6 (6)
N1—C1—H1B109.5C6—C7—C8119.8 (7)
H1A—C1—H1B109.5C6—C7—H7A120.1
N1—C1—H1C109.5C8—C7—H7A120.1
H1A—C1—H1C109.5C9—C8—C7120.0 (7)
H1B—C1—H1C109.5C9—C8—H8A120.0
N1—C2—H2A109.5C7—C8—H8A120.0
N1—C2—H2B109.5C10—C9—C8120.4 (7)
H2A—C2—H2B109.5C10—C9—H9A119.8
N1—C2—H2C109.5C8—C9—H9A119.8
H2A—C2—H2C109.5C9—C10—C11119.5 (7)
H2B—C2—H2C109.5C9—C10—H10A120.2
N1—C3—C4110.6 (6)C11—C10—H10A120.2
N1—C3—H3A109.5C6—C11—C10122.0 (7)
C4—C3—H3A109.5C6—C11—H11A119.0
N1—C3—H3B109.5C10—C11—H11A119.0
C4—C3—H3B109.5Cl1—Fe1—Cl4112.13 (10)
H3A—C3—H3B108.1Cl1—Fe1—Cl3110.63 (11)
C5—C4—C3115.5 (6)Cl4—Fe1—Cl3108.91 (10)
C5—C4—H4A108.4Cl1—Fe1—Cl2108.94 (9)
C3—C4—H4A108.4Cl4—Fe1—Cl2107.93 (8)
C5—C4—H4B108.4Cl3—Fe1—Cl2108.17 (9)
C3—C4—H4B108.4C2—N1—C1110.7 (7)
H4A—C4—H4B107.5C2—N1—C3110.7 (6)
O1—C5—C4120.2 (6)C1—N1—C3105.0 (7)
O1—C5—C6120.6 (6)C2—N1—H1D110.1
C4—C5—C6119.2 (6)C1—N1—H1D110.1
C11—C6—C7118.3 (6)C3—N1—H1D110.1
C11—C6—C5119.1 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1D···O10.912.062.735 (7)130

Experimental details

Crystal data
Chemical formula(C11H16NO)[FeCl4]
Mr375.90
Crystal system, space groupMonoclinic, P21/c
Temperature (K)291
a, b, c (Å)6.3166 (13), 15.149 (3), 17.293 (4)
β (°) 92.55 (3)
V3)1653.1 (6)
Z4
Radiation typeMo Kα
µ (mm1)1.55
Crystal size (mm)0.26 × 0.22 × 0.20
Data collection
DiffractometerRigaku Mercury2
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2005)
Tmin, Tmax0.08, 0.12
No. of measured, independent and
observed [I > 2σ(I)] reflections
15234, 3244, 1895
Rint0.080
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.071, 0.172, 1.11
No. of reflections3244
No. of parameters164
No. of restraints61
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.80, 0.45

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top
Fe1—Cl12.164 (2)Fe1—Cl32.180 (2)
Fe1—Cl22.1854 (18)Fe1—Cl42.179 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1D···O10.912.062.735 (7)130
 

Acknowledgements

The author thanks the Ordered Matter Science Research Centre, Southeast University for support.

References

First citationHay, M. T. & Geib, S. J. (2005). Acta Cryst. E61, m190–m191.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationRigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationTon, C. & Bolte, M. (2004). Acta Cryst. E60, o616–o617.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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