2,9-Dimethyl-1,10-phenanthrolin-1-ium tetra­chloridoferrate(III) methanol monosolvate

Bahojb Noruzi, E.; Safari, N.; Amani, V.; Notash, B.

doi:10.1107/S1600536812025111

metal-organic compounds

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2,9-Dimethyl-1,10-phenanthrolin-1-ium tetrachloridoferrate(III) methanol monosolvate

Ehsan Bahojb Noruzi,^a Nasser Safari,^a ^* Vahid Amani ^a and Behrouz Notash ^a

^aDepartment of Chemistry, Shahid Beheshti University, G. C., Evin, Tehran 1983963113, Iran
^*Correspondence e-mail: n-safari@sbu.ac.ir

(Received 29 May 2012; accepted 1 June 2012; online 13 June 2012)

In the title compound, (C₁₄H₁₃N₂)[FeCl₄]·CH₃OH, the 2,9-dimethyl-1,10-phenanthrolin-1-ium cation, FeCl₄⁻ anion and methanol solvent molecule lie on a twofold rotation axis. Due to symmetry, the H atom on the N atom of the cation is half-occupied. In the anion, the Fe^III atom has a tetrahedral geometry. H atoms of the methanol molecule are disordered over two sets of sites around the twofold axis. In the crystal, π–π contacts between the pyridine rings and between the pyridine and benzene rings [centroid–centroid distances = 3.6535 (16) and 3.5522 (17) Å] and intermolecular O—H⋯N and N—H⋯O hydrogen bonds stabilize the structure.

Related literature

For related structures, see: Abboud et al. (2005 ); Amani et al. (2007 , 2009 ); Khavasi et al. (2008 ); Moreno et al. (2006 ); Morsali (2005 ); Veidis et al. (1981 ); Yousefi et al. (2007 ); Yu et al. (2006 ).

Experimental

Crystal data

(C₁₄H₁₃N₂)[FeCl₄]·CH₄O
M_r = 438.96
Monoclinic, C 2/c
a = 13.067 (3) Å
b = 20.377 (4) Å
c = 7.2810 (15) Å
β = 109.03 (3)°
V = 1832.7 (7) Å³
Z = 4
Mo Kα radiation
μ = 1.41 mm⁻¹
T = 120 K
0.20 × 0.15 × 0.10 mm

Data collection

Stoe IPDS-2T diffractometer
Absorption correction: numerical (X-SHAPE and X-RED; Stoe & Cie, 2002 ) T_min = 0.766, T_max = 0.872
9967 measured reflections
2464 independent reflections
2075 reflections with I > 2σ(I)
R_int = 0.049

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.099
S = 1.10
2464 reflections
112 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.84 e Å⁻³
Δρ_min = −0.84 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.84	2.33	2.751 (4)	112
N1—H1D⋯O1	0.65 (12)	2.10 (10)	2.751 (4)	175 (14)

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812025111/hy2554sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812025111/hy2554Isup2.hkl

checkCIF report

Comment top

In the recent years, we reported the synthesis and crystal structures of iron(III) proton transfer complexes, such as [Fe(bipy)Cl₄][bipy.H] (Amani et al., 2007), [Fe(phen)Cl₄][phen.H] (Khavasi et al., 2008), [Fe(4,4'-dmbpy)Cl₄][4,4'-dmbpy.H] (Amani et al., 2009) (bipy = 2,2'-bipyridine, phen = 1,10-phenanthroline, 4,4'-dmbpy = 4,4'-dimethyl-2,2'-bipyridine). Several proton transfer systems using 2,9-dimethyl-1,10-phenanthroline as proton donor molecules, such as [Me₂phen.H](ClO₄) (Morsali, 2005), [Me₂phen.H](NO₃) (Yu et al., 2006), [Me₂phen.H][Ru(CO)₃Cl₃] (Moreno et al., 2006) and [Me₂phen.H]₂[PtCl₆] (Yousefi et al., 2007) (Me₂phen.H = 2,9-dimethyl-1,10-phenanthrolinium) have been synthesized and characterized by single-crystal X-ray diffraction methods. Also, the structure of [Me₂phen.H][FeCl₄] was reported (Veidis et al., 1981). We report herein the synthesis and crystal structure of the title compound.

The molecular structure of the title compound is shown in Fig. 1. The asymmetric unit of the title compound contains half of a protonated 2,9-dimethyl-1,10-phenanthrolinium cation, half of a FeCl₄^- anion and half of a methanol solvent molecule. In the anion, the Fe^III atom has a tetrahedral coordination. The Fe—Cl bond lengths and angles are within normal range (Abboud et al., 2005; Amani et al., 2007). In the crystal, intermolecular O—H···N and N—H···O hydrogen bonds (Table 1) and π–π interactions between the pyridine and benzene rings, Cg1···Cg1ⁱ = 3.6535 (16) and Cg1···Cg2ⁱⁱ = 3.5522 (17) Å [Cg1 and Cg2 are the centroids of the N1/C2–C6 ring and the C5, C6, C7, C5ⁱⁱⁱ, C6ⁱⁱⁱ, C7ⁱⁱⁱ ring; symmetry codes: (i) x, 1-y, -1/2+z; (ii) 2-x, 1-y, -z; (iii) 2-x, y, 1/2-z], stabilize the structure (Fig. 2).

Related literature top

For related structures, see: Abboud et al. (2005); Amani et al. (2007, 2009); Khavasi et al. (2008); Moreno et al. (2006); Morsali (2005); Veidis et al. (1981); Yousefi et al. (2007); Yu et al. (2006).

Experimental top

For the preparation of the title compound, a solution of 2,9-dimethyl-1,10-phenanthroline (0.25 g, 1.20 mmol) in acetonitrile (10 ml) was added to a solution of FeCl₃.6H₂O (0.11 g, 0.40 mmol) in methanol (10 ml) and the resulting yellow solution was stirred at 313 K for 2 h. This solution was left to evaporate slowly at room temperature. After 5 days, yellow needle crystals of the title compound were isolated (yield: 0.13 g, 74.0%; m. p. 426 K).

Structure description top

For related structures, see: Abboud et al. (2005); Amani et al. (2007, 2009); Khavasi et al. (2008); Moreno et al. (2006); Morsali (2005); Veidis et al. (1981); Yousefi et al. (2007); Yu et al. (2006).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. [Symmetry code: (i) 2-x, y, 1/2-z.]
	Fig. 2. Crystal packing diagram for the title compound. Hydrogen bonds are shown as dashed lines.

2,9-Dimethyl-1,10-phenanthrolin-1-ium tetrachloridoferrate(III) methanol monosolvate top

Crystal data top

(C₁₄H₁₃N₂)[FeCl₄]·CH₄O	F(000) = 892
M_r = 438.96	D_x = 1.591 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2464 reflections
a = 13.067 (3) Å	θ = 3.1–29.2°
b = 20.377 (4) Å	µ = 1.41 mm⁻¹
c = 7.2810 (15) Å	T = 120 K
β = 109.03 (3)°	Needle, yellow
V = 1832.7 (7) Å³	0.20 × 0.15 × 0.10 mm
Z = 4

Data collection top

Stoe IPDS-2T diffractometer	2464 independent reflections
Radiation source: fine-focus sealed tube	2075 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
ω scans	θ_max = 29.2°, θ_min = 3.1°
Absorption correction: numerical (X-SHAPE and X-RED; Stoe & Cie, 2002)	h = −17→17
T_min = 0.766, T_max = 0.872	k = −27→27
9967 measured reflections	l = −9→9

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.099	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ²(F_o²) + (0.0412P)² + 3.5467P] where P = (F_o² + 2F_c²)/3
2464 reflections	(Δ/σ)_max = 0.001
112 parameters	Δρ_max = 0.84 e Å⁻³
0 restraints	Δρ_min = −0.84 e Å⁻³

Crystal data top

(C₁₄H₁₃N₂)[FeCl₄]·CH₄O	V = 1832.7 (7) Å³
M_r = 438.96	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 13.067 (3) Å	µ = 1.41 mm⁻¹
b = 20.377 (4) Å	T = 120 K
c = 7.2810 (15) Å	0.20 × 0.15 × 0.10 mm
β = 109.03 (3)°

Data collection top

Stoe IPDS-2T diffractometer	2464 independent reflections
Absorption correction: numerical (X-SHAPE and X-RED; Stoe & Cie, 2002)	2075 reflections with I > 2σ(I)
T_min = 0.766, T_max = 0.872	R_int = 0.049
9967 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.099	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	Δρ_max = 0.84 e Å⁻³
2464 reflections	Δρ_min = −0.84 e Å⁻³
112 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	Occ. (<1)
Fe1	1.0000	0.15100 (2)	0.2500	0.01928 (13)
Cl1	0.85420 (5)	0.21251 (3)	0.17847 (11)	0.03440 (18)
Cl2	0.99637 (5)	0.08774 (3)	0.00604 (10)	0.03183 (17)
O1	1.0000	0.68189 (19)	0.2500	0.139 (3)
H1	0.9766	0.6682	0.1350	0.208*	0.50
N1	0.89657 (16)	0.56531 (10)	0.1150 (3)	0.0181 (4)
C1	0.7488 (2)	0.63346 (14)	−0.0768 (4)	0.0304 (6)
H1A	0.7225	0.6522	0.0235	0.046*
H1B	0.6883	0.6291	−0.1985	0.046*
H1C	0.8039	0.6624	−0.0974	0.046*
C2	0.79690 (19)	0.56745 (13)	−0.0131 (3)	0.0232 (5)
C3	0.7407 (2)	0.50876 (14)	−0.0831 (4)	0.0290 (6)
H3	0.6692	0.5103	−0.1729	0.035*
C4	0.7888 (2)	0.44989 (14)	−0.0223 (4)	0.0305 (6)
H4	0.7508	0.4105	−0.0709	0.037*
C5	0.8949 (2)	0.44681 (12)	0.1129 (4)	0.0242 (5)
C6	0.94610 (18)	0.50710 (11)	0.1799 (3)	0.0178 (4)
C7	0.9500 (2)	0.38679 (12)	0.1836 (4)	0.0323 (6)
H7	0.9157	0.3462	0.1363	0.039*
C8	1.0000	0.7446 (2)	0.2500	0.073 (2)
H8A	0.9305	0.7606	0.2564	0.088*	0.50
H8B	1.0107	0.7606	0.1307	0.088*	0.50
H8C	1.0587	0.7606	0.3629	0.088*	0.50
H1D	0.924 (9)	0.592 (5)	0.147 (16)	0.088*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.0158 (2)	0.0150 (2)	0.0223 (2)	0.000	−0.00025 (17)	0.000
Cl1	0.0220 (3)	0.0221 (3)	0.0523 (4)	0.0066 (2)	0.0028 (3)	0.0083 (3)
Cl2	0.0328 (3)	0.0324 (3)	0.0289 (3)	−0.0084 (3)	0.0083 (3)	−0.0095 (2)
O1	0.154 (5)	0.0212 (19)	0.141 (5)	0.000	−0.090 (5)	0.000
N1	0.0187 (9)	0.0185 (9)	0.0181 (9)	−0.0025 (7)	0.0074 (7)	−0.0004 (7)
C1	0.0194 (11)	0.0393 (15)	0.0290 (13)	0.0023 (10)	0.0030 (9)	0.0067 (11)
C2	0.0200 (11)	0.0314 (13)	0.0195 (11)	−0.0052 (9)	0.0085 (9)	−0.0008 (9)
C3	0.0216 (11)	0.0415 (15)	0.0254 (12)	−0.0124 (10)	0.0097 (10)	−0.0077 (11)
C4	0.0309 (13)	0.0343 (14)	0.0327 (14)	−0.0189 (11)	0.0192 (11)	−0.0154 (11)
C5	0.0307 (12)	0.0204 (11)	0.0297 (13)	−0.0092 (10)	0.0211 (10)	−0.0062 (9)
C6	0.0192 (10)	0.0181 (10)	0.0193 (10)	−0.0012 (8)	0.0107 (9)	−0.0012 (8)
C7	0.0450 (15)	0.0153 (11)	0.0507 (17)	−0.0049 (10)	0.0349 (14)	−0.0062 (10)
C8	0.099 (5)	0.026 (2)	0.070 (4)	0.000	−0.005 (4)	0.000

Geometric parameters (Å, º) top

Fe1—Cl2	2.1826 (8)	C2—C3	1.409 (4)
Fe1—Cl2ⁱ	2.1826 (8)	C3—C4	1.359 (4)
Fe1—Cl1ⁱ	2.1966 (8)	C3—H3	0.9500
Fe1—Cl1	2.1966 (8)	C4—C5	1.416 (4)
O1—C8	1.277 (6)	C4—H4	0.9500
O1—H1	0.8400	C5—C6	1.408 (3)
N1—C2	1.333 (3)	C5—C7	1.427 (4)
N1—C6	1.360 (3)	C6—C6ⁱ	1.445 (4)
N1—H1D	0.64 (11)	C7—C7ⁱ	1.349 (6)
C1—C2	1.493 (4)	C7—H7	0.9500
C1—H1A	0.9800	C8—H8A	0.9800
C1—H1B	0.9800	C8—H8B	0.9800
C1—H1C	0.9800	C8—H8C	0.9800

Cl2—Fe1—Cl2ⁱ	107.61 (5)	C4—C3—H3	120.0
Cl2—Fe1—Cl1ⁱ	108.48 (3)	C2—C3—H3	120.0
Cl2ⁱ—Fe1—Cl1ⁱ	110.92 (4)	C3—C4—C5	120.6 (2)
Cl2—Fe1—Cl1	110.92 (4)	C3—C4—H4	119.7
Cl2ⁱ—Fe1—Cl1	108.48 (3)	C5—C4—H4	119.7
Cl1ⁱ—Fe1—Cl1	110.41 (4)	C6—C5—C4	116.7 (2)
C8—O1—H1	109.5	C6—C5—C7	119.7 (2)
C2—N1—C6	121.2 (2)	C4—C5—C7	123.6 (2)
C2—N1—H1D	122 (10)	N1—C6—C5	121.5 (2)
C6—N1—H1D	117 (10)	N1—C6—C6ⁱ	119.29 (12)
C2—C1—H1A	109.5	C5—C6—C6ⁱ	119.25 (14)
C2—C1—H1B	109.5	C7ⁱ—C7—C5	121.03 (16)
H1A—C1—H1B	109.5	C7ⁱ—C7—H7	119.5
C2—C1—H1C	109.5	C5—C7—H7	119.5
H1A—C1—H1C	109.5	O1—C8—H8A	109.5
H1B—C1—H1C	109.5	O1—C8—H8B	109.5
N1—C2—C3	120.0 (2)	H8A—C8—H8B	109.5
N1—C2—C1	117.6 (2)	O1—C8—H8C	109.5
C3—C2—C1	122.3 (2)	H8A—C8—H8C	109.5
C4—C3—C2	120.0 (2)	H8B—C8—H8C	109.5

C6—N1—C2—C3	0.3 (3)	C2—N1—C6—C6ⁱ	−179.5 (3)
C6—N1—C2—C1	−179.8 (2)	C4—C5—C6—N1	−1.1 (3)
N1—C2—C3—C4	−1.0 (4)	C7—C5—C6—N1	179.5 (2)
C1—C2—C3—C4	179.1 (3)	C4—C5—C6—C6ⁱ	179.2 (3)
C2—C3—C4—C5	0.6 (4)	C7—C5—C6—C6ⁱ	−0.2 (4)
C3—C4—C5—C6	0.4 (4)	C6—C5—C7—C7ⁱ	1.1 (5)
C3—C4—C5—C7	179.7 (3)	C4—C5—C7—C7ⁱ	−178.2 (3)
C2—N1—C6—C5	0.8 (3)

Symmetry code: (i) −x+2, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.84	2.33	2.751 (4)	112
N1—H1D···O1	0.65 (12)	2.10 (10)	2.751 (4)	175 (14)

Experimental details

Crystal data
Chemical formula	(C₁₄H₁₃N₂)[FeCl₄]·CH₄O
M_r	438.96
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	120
a, b, c (Å)	13.067 (3), 20.377 (4), 7.2810 (15)
β (°)	109.03 (3)
V (Å³)	1832.7 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.41
Crystal size (mm)	0.20 × 0.15 × 0.10

Data collection
Diffractometer	Stoe IPDS2T
Absorption correction	Numerical (X-SHAPE and X-RED; Stoe & Cie, 2002)
T_min, T_max	0.766, 0.872
No. of measured, independent and observed [I > 2σ(I)] reflections	9967, 2464, 2075
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.685

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.099, 1.10
No. of reflections	2464
No. of parameters	112
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.84, −0.84

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.84	2.3300	2.751 (4)	112.00
N1—H1D···O1	0.65 (12)	2.10 (10)	2.751 (4)	175 (14)

Acknowledgements

We are grateful to the Shahid Beheshti University for financial support.

References

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

2,9-Di­methyl-1,10-phenanthrolin-1-ium tetra­chloridoferrate(III) methanol monosolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

2,9-Dimethyl-1,10-phenanthrolin-1-ium tetrachloridoferrate(III) methanol monosolvate