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

Jin, L.

doi:10.1107/S1600536812018600

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page m709

doi:10.1107/S1600536812018600

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

Lei Jin ^a ^*

^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 ); Ton & Bolte (2004 ).

Experimental

Crystal data

(C₁₁H₁₆NO)[FeCl₄]
M_r = 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 ) T_min = 0.08, T_max = 0.12
15234 measured reflections
3244 independent reflections
1895 reflections with I > 2σ(I)
R_int = 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
Δρ_max = 0.80 e Å⁻³
Δρ_min = −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	D⋯A	D—H⋯A
N1—H1D⋯O1	0.91	2.06	2.735 (7)	130

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812018600/hb6733sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812018600/hb6733Isup2.hkl

checkCIF report

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

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
M_r = 375.90	F(000) = 764
Monoclinic, P2₁/c	D_x = 1.510 Mg m⁻³
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 6.3166 (13) Å	θ = 3.2–26°
b = 15.149 (3) Å	µ = 1.55 mm⁻¹
c = 17.293 (4) Å	T = 291 K
β = 92.55 (3)°	Block, yellow
V = 1653.1 (6) Å³	0.26 × 0.22 × 0.20 mm

Data collection top

Rigaku Mercury2 diffractometer	3244 independent reflections
Radiation source: fine-focus sealed tube	1895 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.080
Detector resolution: 13.6612 pixels mm^-1	θ_max = 26.0°, θ_min = 3.2°
CCD_Profile_fitting scans	h = −7→7
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −18→18
T_min = 0.08, T_max = 0.12	l = −21→21
15234 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.071	H-atom parameters constrained
wR(F²) = 0.172	w = 1/[σ²(F_o²) + (0.0538P)² + 2.3762P] where P = (F_o² + 2F_c²)/3
S = 1.11	(Δ/σ)_max < 0.001
3244 reflections	Δρ_max = 0.80 e Å⁻³
164 parameters	Δρ_min = −0.45 e Å⁻³
61 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0126 (14)

Crystal data top

(C₁₁H₁₆NO)[FeCl₄]	V = 1653.1 (6) Å³
M_r = 375.90	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.3166 (13) Å	µ = 1.55 mm⁻¹
b = 15.149 (3) Å	T = 291 K
c = 17.293 (4) Å	0.26 × 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)
T_min = 0.08, T_max = 0.12	R_int = 0.080
15234 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.071	61 restraints
wR(F²) = 0.172	H-atom parameters constrained
S = 1.11	Δρ_max = 0.80 e Å⁻³
3244 reflections	Δρ_min = −0.45 e Å⁻³
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

	x	y	z	U_iso*/U_eq
C1	−0.0240 (17)	0.4076 (6)	0.9427 (6)	0.135 (3)
H1A	−0.0142	0.3960	0.9974	0.203*
H1B	−0.1631	0.4292	0.9285	0.203*
H1C	0.0797	0.4510	0.9301	0.203*
C2	0.0080 (15)	0.3420 (6)	0.8157 (5)	0.120 (3)
H2A	0.0347	0.2878	0.7890	0.180*
H2B	0.1140	0.3847	0.8037	0.180*
H2C	−0.1294	0.3641	0.7995	0.180*
C3	−0.1593 (13)	0.2645 (5)	0.9215 (5)	0.102 (2)
H3A	−0.2943	0.2879	0.9020	0.122*
H3B	−0.1629	0.2603	0.9774	0.122*
C4	−0.1252 (11)	0.1715 (4)	0.8870 (4)	0.0829 (19)
H4A	−0.2390	0.1335	0.9027	0.099*
H4B	−0.1363	0.1760	0.8310	0.099*
C5	0.0813 (10)	0.1284 (4)	0.9097 (3)	0.0627 (16)
C6	0.1018 (9)	0.0308 (4)	0.9021 (3)	0.0547 (14)
C7	−0.0662 (11)	−0.0227 (4)	0.8783 (4)	0.0745 (19)
H7A	−0.1985	0.0019	0.8663	0.089*
C8	−0.0368 (14)	−0.1134 (5)	0.8724 (4)	0.088 (2)
H8A	−0.1491	−0.1495	0.8559	0.106*
C9	0.1574 (15)	−0.1496 (5)	0.8908 (4)	0.088 (2)
H9A	0.1770	−0.2102	0.8863	0.105*
C10	0.3218 (13)	−0.0976 (5)	0.9157 (5)	0.087 (2)
H10A	0.4528	−0.1225	0.9292	0.104*
C11	0.2933 (10)	−0.0084 (4)	0.9206 (4)	0.0701 (18)
H11A	0.4071	0.0269	0.9371	0.084*
Cl1	0.4836 (3)	0.50465 (14)	0.21112 (15)	0.1142 (8)
Cl2	0.0148 (3)	0.38087 (12)	0.17367 (12)	0.0850 (6)
Cl3	0.4451 (4)	0.3546 (2)	0.05173 (13)	0.1258 (9)
Cl4	0.4761 (3)	0.26961 (14)	0.24300 (13)	0.0987 (7)
Fe1	0.36032 (13)	0.37873 (5)	0.17073 (5)	0.0576 (3)
N1	0.0153 (9)	0.3257 (3)	0.9003 (3)	0.0745 (14)
H1D	0.1432	0.3026	0.9159	0.089*
O1	0.2302 (8)	0.1727 (3)	0.9339 (3)	0.0893 (16)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.165 (7)	0.114 (6)	0.123 (6)	0.047 (6)	−0.041 (6)	−0.034 (5)
C2	0.120 (6)	0.129 (6)	0.113 (6)	0.022 (5)	0.023 (5)	−0.006 (5)
C3	0.100 (5)	0.096 (4)	0.109 (5)	0.026 (4)	0.006 (4)	0.010 (4)
C4	0.080 (4)	0.065 (4)	0.102 (4)	0.010 (3)	−0.014 (3)	0.003 (3)
C5	0.074 (4)	0.057 (4)	0.056 (4)	0.002 (3)	−0.011 (3)	0.005 (3)
C6	0.064 (4)	0.055 (4)	0.045 (3)	0.003 (3)	0.003 (3)	0.002 (3)
C7	0.079 (5)	0.071 (5)	0.072 (5)	0.001 (4)	−0.007 (4)	−0.005 (4)
C8	0.103 (6)	0.069 (5)	0.092 (6)	−0.020 (5)	0.001 (4)	−0.018 (4)
C9	0.122 (7)	0.061 (4)	0.081 (5)	0.010 (5)	0.011 (5)	−0.005 (4)
C10	0.089 (5)	0.071 (5)	0.100 (6)	0.022 (4)	0.001 (4)	−0.002 (4)
C11	0.072 (4)	0.062 (4)	0.076 (5)	0.005 (3)	−0.001 (3)	0.004 (3)
Cl1	0.0904 (15)	0.0800 (13)	0.170 (2)	−0.0095 (11)	−0.0163 (14)	−0.0386 (14)
Cl2	0.0490 (9)	0.0881 (13)	0.1176 (16)	0.0042 (9)	0.0013 (9)	0.0156 (11)
Cl3	0.1048 (16)	0.197 (3)	0.0762 (14)	0.0392 (17)	0.0098 (11)	−0.0246 (15)
Cl4	0.0720 (12)	0.0990 (14)	0.1228 (17)	0.0033 (11)	−0.0227 (11)	0.0345 (12)
Fe1	0.0481 (5)	0.0582 (6)	0.0660 (6)	0.0028 (4)	−0.0023 (4)	−0.0042 (4)
N1	0.081 (3)	0.061 (3)	0.081 (3)	0.013 (3)	−0.011 (3)	−0.004 (3)
O1	0.090 (3)	0.061 (3)	0.113 (4)	0.000 (3)	−0.041 (3)	−0.003 (3)

Geometric parameters (Å, º) top

C1—N1	1.468 (9)	C6—C11	1.372 (8)
C1—H1A	0.9600	C6—C7	1.383 (8)
C1—H1B	0.9600	C7—C8	1.391 (9)
C1—H1C	0.9600	C7—H7A	0.9300
C2—N1	1.483 (10)	C8—C9	1.368 (11)
C2—H2A	0.9600	C8—H8A	0.9300
C2—H2B	0.9600	C9—C10	1.358 (10)
C2—H2C	0.9600	C9—H9A	0.9300
C3—N1	1.499 (9)	C10—C11	1.367 (9)
C3—C4	1.548 (10)	C10—H10A	0.9300
C3—H3A	0.9700	C11—H11A	0.9300
C3—H3B	0.9700	Fe1—Cl1	2.164 (2)
C4—C5	1.495 (8)	Fe1—Cl2	2.1854 (18)
C4—H4A	0.9700	Fe1—Cl3	2.180 (2)
C4—H4B	0.9700	Fe1—Cl4	2.179 (2)
C5—O1	1.214 (7)	N1—H1D	0.9100
C5—C6	1.492 (8)

N1—C1—H1A	109.5	C7—C6—C5	122.6 (6)
N1—C1—H1B	109.5	C6—C7—C8	119.8 (7)
H1A—C1—H1B	109.5	C6—C7—H7A	120.1
N1—C1—H1C	109.5	C8—C7—H7A	120.1
H1A—C1—H1C	109.5	C9—C8—C7	120.0 (7)
H1B—C1—H1C	109.5	C9—C8—H8A	120.0
N1—C2—H2A	109.5	C7—C8—H8A	120.0
N1—C2—H2B	109.5	C10—C9—C8	120.4 (7)
H2A—C2—H2B	109.5	C10—C9—H9A	119.8
N1—C2—H2C	109.5	C8—C9—H9A	119.8
H2A—C2—H2C	109.5	C9—C10—C11	119.5 (7)
H2B—C2—H2C	109.5	C9—C10—H10A	120.2
N1—C3—C4	110.6 (6)	C11—C10—H10A	120.2
N1—C3—H3A	109.5	C6—C11—C10	122.0 (7)
C4—C3—H3A	109.5	C6—C11—H11A	119.0
N1—C3—H3B	109.5	C10—C11—H11A	119.0
C4—C3—H3B	109.5	Cl1—Fe1—Cl4	112.13 (10)
H3A—C3—H3B	108.1	Cl1—Fe1—Cl3	110.63 (11)
C5—C4—C3	115.5 (6)	Cl4—Fe1—Cl3	108.91 (10)
C5—C4—H4A	108.4	Cl1—Fe1—Cl2	108.94 (9)
C3—C4—H4A	108.4	Cl4—Fe1—Cl2	107.93 (8)
C5—C4—H4B	108.4	Cl3—Fe1—Cl2	108.17 (9)
C3—C4—H4B	108.4	C2—N1—C1	110.7 (7)
H4A—C4—H4B	107.5	C2—N1—C3	110.7 (6)
O1—C5—C4	120.2 (6)	C1—N1—C3	105.0 (7)
O1—C5—C6	120.6 (6)	C2—N1—H1D	110.1
C4—C5—C6	119.2 (6)	C1—N1—H1D	110.1
C11—C6—C7	118.3 (6)	C3—N1—H1D	110.1
C11—C6—C5	119.1 (6)

Hydrogen-bond geometry (Å, º) top

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

Experimental details

Crystal data
Chemical formula	(C₁₁H₁₆NO)[FeCl₄]
M_r	375.90
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	291
a, b, c (Å)	6.3166 (13), 15.149 (3), 17.293 (4)
β (°)	92.55 (3)
V (Å³)	1653.1 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.55
Crystal size (mm)	0.26 × 0.22 × 0.20

Data collection
Diffractometer	Rigaku Mercury2 diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.08, 0.12
No. of measured, independent and observed [I > 2σ(I)] reflections	15234, 3244, 1895
R_int	0.080
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.071, 0.172, 1.11
No. of reflections	3244
No. of parameters	164
No. of restraints	61
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.80, −0.45

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

Selected bond lengths (Å) top

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

Hydrogen-bond geometry (Å, º) top

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

Acknowledgements

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

References

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