cis-Bis(2,2′-bipyridine-κ2N,N′)dichlorido­iron(III) perchlorate

Zhang, Z.-F.

doi:10.1107/S1600536811016035

metal-organic compounds

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Volume 67| Part 6| June 2011| Page m677

doi:10.1107/S1600536811016035

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cis-Bis(2,2′-bipyridine-κ²N,N′)dichloridoiron(III) perchlorate

Zhi-Fang Zhang ^a ^*

^aSchool of Chemistry and Chemical Engineering, Yulin University, Yulin 719000, People's Republic of China
^*Correspondence e-mail: zhifang889@126.com

(Received 11 April 2011; accepted 27 April 2011; online 7 May 2011)

In the crystal structure of the title compound, [FeCl₂(C₁₀H₈N₂)₂]ClO₄, the coordination around the Fe^III atom is approximately octahedral. The equatorial positions are occupied by two N atoms from two 2,2′-bipyridyl ligands [Fe—N = 2.121 (5) and 2.147 (5) Å] and two Cl atoms [Fe—Cl = 2.220 (2) and 2.2074 (18) Å]. Weak intermolecular C—H⋯O and C—H⋯Cl hydrogen bonds and C—H⋯π interactions consolidate the crystal packing.

Related literature

For the use of bipyridine and analogous ligands in the formation of transition metal complexes, see: Constable (1989 ). For applications of related compounds, see: Constable & Steel (1989 ); Steel et al. (1990 ). For related structures, see: Amani et al. (2007 ); Figgis et al. (1983 ).

Experimental

Crystal data

[FeCl₂(C₁₀H₈N₂)₂]ClO₄
M_r = 538.57
Orthorhombic, P 2₁ 2₁ 2₁
a = 10.891 (2) Å
b = 11.522 (2) Å
c = 16.990 (3) Å
V = 2132.1 (7) Å³
Z = 4
Mo Kα radiation
μ = 1.12 mm⁻¹
T = 295 K
0.34 × 0.29 × 0.24 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.702, T_max = 0.775
5914 measured reflections
3534 independent reflections
2810 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.063
wR(F²) = 0.125
S = 1.08
3534 reflections
289 parameters
H-atom parameters constrained
Δρ_max = 0.75 e Å⁻³
Δρ_min = −0.42 e Å⁻³
Absolute structure: Flack (1983 ), 1419 Friedel pairs
Flack parameter: 0.05 (3)

Table 1
Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the N2,C6–C10 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O2	0.93	2.52	3.140 (11)	124
C7—H7⋯O3ⁱ	0.93	2.55	3.239 (9)	131
C8—H8⋯O2ⁱⁱ	0.93	2.30	3.152 (9)	152
C13—H13⋯O2ⁱⁱⁱ	0.93	2.54	3.423 (10)	158
C18—H18⋯O4^iv	0.93	2.51	3.387 (10)	158
C10—H10⋯Cl3	0.93	2.71	3.308 (7)	122
C20—H20⋯Cl2	0.93	2.79	3.382 (7)	123
C11—H11⋯Cg4	0.93	2.90	3.705 (8)	146
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ ; (ii) $[-x+{\script{3\over 2}}, -y+1, z-{\script{1\over 2}}]$ ; (iii) x+1, y, z; (iv) $[-x+{\script{3\over 2}}, -y+1, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT-Plus (Bruker, 2003 ); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811016035/zq2098sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811016035/zq2098Isup2.hkl

checkCIF report

Comment top

Bipyridine and analogous ligands such as phenanthroline are commonly used in the formation of different complexes with a general variety of transition metals (Constable, 1989). Studies of these transition metal complexes are important in understanding electron transfer processes, mixed valence complexes, magnetic coupling and magnetic transitions (Constable et al., 1989; Steel et al., 1990). Although bipyridine coordination to iron has been widely investigated, most complexes are iron(II) complexes, little attention has been paid to bipyridine iron(III) complexes. In order to expand this field, the title compound has been synthesized, and its crystal structure is reported herein.

The molecular structure of the title compound (I) is shown in Fig. 1. The crystal is composed of cis-[Fe^III(bipy)₂C1₂]⁺ cations and [C1O₄]^- anions. The Fe^III atom is coordinated by two Cl anions and four N atoms from two 2,2'-bipyridyl ligands within a distorted octahedral geometry. The six-coordinate molecule is the cis-cis isomer considering the positions of the chlorine and pyridyl nitrogen atoms. The four Fe—N bond lengths [2.087 (4)–2.147 (5) Å] were similar and consistent with those reported earlier (Amani et al., 2007; Figgis et al., 1983). The distortion from a perfect octahedral geometry was primarily a consequence of the small bite-angle of the chelating ligands, which led to acute N1—Fe—N2 and N3—Fe—N4 angles of 75.96 (19)° and 75.4 (2)°, respectively.

Intermolecular C—H···O, C—H···Cl hydrogen bonds and C—H···π interactions stabilize the crystal structure (Table 1).

Related literature top

For the use of bipyridine and analogous ligands in the formation of transition metal complexes, see: Constable (1989). For applications of related compounds, see: Constable & Steel (1989); Steel et al. (1990). For related structures, see: Amani et al. (2007); Figgis et al. (1983).

Experimental top

All reagents were obtained from commercial sources and used without further purification. 2,2'-Bipyridine (0.312 g, 2.0 mmol) and NaClO₄ (0.122 g,1.0 mmol) were added to a solution of FeCl₃.6H₂O (0.270 g, 1.0 mmol) in methanol (30 ml), and the solution was stirred at 60–65 ^oC for 3 h. A red-brown precipitate was obtained. After filtration, the red-brown filtrate was allowed to stand at room temperature for two weeks to give red-brown block-shaped crystals suitable for X-ray analysis. Elemental analysis for C₂₀H₁₆Cl₃FeN₄O₄: C 44.60, H 2.99, N 10.40 %; found: C 44.52, H 3.03, N 10.39 %.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus (Bruker, 2003); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (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 thermal ellipsoids at the 30% probability level.

cis-Bis(2,2'-bipyridine-κ²N,N')dichloridoiron(III) perchlorate top

Crystal data top

[FeCl₂(C₁₀H₈N₂)₂]ClO₄	F(000) = 1092
M_r = 538.57	D_x = 1.678 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1783 reflections
a = 10.891 (2) Å	θ = 2.4–25.9°
b = 11.522 (2) Å	µ = 1.12 mm⁻¹
c = 16.990 (3) Å	T = 295 K
V = 2132.1 (7) Å³	Block, red-brown
Z = 4	0.34 × 0.29 × 0.24 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	3534 independent reflections
Radiation source: fine-focus sealed tube	2810 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
ϕ and ω scans	θ_max = 25.0°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −7→12
T_min = 0.702, T_max = 0.775	k = −12→13
5914 measured reflections	l = −20→17

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)] = 0.063	H-atom parameters constrained
wR(F²) = 0.125	w = 1/[σ²(F_o²) + (0.043P)² + 0.4377P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max = 0.001
3534 reflections	Δρ_max = 0.75 e Å⁻³
289 parameters	Δρ_min = −0.42 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1419 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.05 (3)

Crystal data top

[FeCl₂(C₁₀H₈N₂)₂]ClO₄	V = 2132.1 (7) Å³
M_r = 538.57	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 10.891 (2) Å	µ = 1.12 mm⁻¹
b = 11.522 (2) Å	T = 295 K
c = 16.990 (3) Å	0.34 × 0.29 × 0.24 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	3534 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	2810 reflections with I > 2σ(I)
T_min = 0.702, T_max = 0.775	R_int = 0.038
5914 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.063	H-atom parameters constrained
wR(F²) = 0.125	Δρ_max = 0.75 e Å⁻³
S = 1.08	Δρ_min = −0.42 e Å⁻³
3534 reflections	Absolute structure: Flack (1983), 1419 Friedel pairs
289 parameters	Absolute structure parameter: 0.05 (3)
0 restraints

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
Fe1	0.97563 (9)	0.23098 (7)	0.13357 (5)	0.0557 (3)
Cl1	0.4647 (2)	0.80918 (14)	0.13791 (10)	0.0674 (5)
Cl2	0.79726 (18)	0.13772 (13)	0.13412 (11)	0.0693 (5)
Cl3	1.10061 (18)	0.08017 (14)	0.13284 (11)	0.0722 (5)
O1	0.5403 (7)	0.8608 (5)	0.0835 (3)	0.111 (2)
O2	0.5221 (7)	0.7174 (5)	0.1726 (3)	0.127 (2)
O3	0.4321 (8)	0.8861 (5)	0.1958 (3)	0.139 (3)
O4	0.3639 (7)	0.7708 (8)	0.0978 (4)	0.164 (3)
N1	0.8727 (5)	0.3863 (4)	0.1221 (3)	0.0511 (13)
N2	0.9729 (5)	0.2621 (4)	0.0126 (3)	0.0499 (12)
N3	1.1301 (5)	0.3461 (4)	0.1420 (3)	0.0551 (13)
N4	0.9974 (5)	0.2596 (4)	0.2546 (3)	0.0529 (13)
C1	0.8236 (7)	0.4446 (6)	0.1798 (4)	0.067 (2)
H1	0.8394	0.4209	0.2311	0.080*
C2	0.7503 (8)	0.5385 (6)	0.1681 (5)	0.079 (3)
H2	0.7126	0.5762	0.2101	0.095*
C3	0.7341 (8)	0.5753 (6)	0.0926 (5)	0.076 (2)
H3	0.6866	0.6406	0.0823	0.092*
C4	0.7870 (8)	0.5169 (6)	0.0333 (4)	0.065 (2)
H4	0.7762	0.5419	−0.0183	0.078*
C5	0.8558 (6)	0.4220 (5)	0.0484 (4)	0.0481 (15)
C6	0.9143 (6)	0.3543 (5)	−0.0115 (3)	0.0475 (15)
C7	0.9110 (8)	0.3798 (6)	−0.0911 (4)	0.067 (2)
H7	0.8674	0.4442	−0.1086	0.081*
C8	0.9698 (7)	0.3129 (7)	−0.1431 (4)	0.073 (2)
H8	0.9702	0.3321	−0.1963	0.087*
C9	1.0269 (7)	0.2198 (6)	−0.1181 (4)	0.0691 (19)
H9	1.0661	0.1710	−0.1538	0.083*
C10	1.0287 (7)	0.1949 (5)	−0.0396 (4)	0.0604 (17)
H10	1.0701	0.1291	−0.0223	0.072*
C11	1.1910 (7)	0.3941 (6)	0.0843 (4)	0.0658 (19)
H11	1.1659	0.3775	0.0333	0.079*
C12	1.2875 (9)	0.4658 (6)	0.0934 (5)	0.079 (2)
H12	1.3255	0.5006	0.0504	0.094*
C13	1.3264 (8)	0.4850 (6)	0.1671 (5)	0.079 (2)
H13	1.3935	0.5331	0.1762	0.095*
C14	1.2681 (8)	0.4344 (6)	0.2280 (4)	0.070 (2)
H14	1.2965	0.4458	0.2790	0.084*
C15	1.1680 (7)	0.3669 (5)	0.2151 (4)	0.0533 (16)
C16	1.0945 (7)	0.3178 (5)	0.2775 (4)	0.0564 (18)
C17	1.1226 (8)	0.3310 (5)	0.3553 (4)	0.072 (2)
H17	1.1922	0.3722	0.3703	0.087*
C18	1.0481 (10)	0.2833 (7)	0.4102 (4)	0.085 (3)
H18	1.0670	0.2904	0.4633	0.102*
C19	0.9466 (9)	0.2257 (7)	0.3879 (4)	0.086 (3)
H19	0.8932	0.1947	0.4251	0.104*
C20	0.9236 (8)	0.2136 (6)	0.3085 (4)	0.078 (2)
H20	0.8548	0.1722	0.2923	0.094*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.0563 (6)	0.0609 (5)	0.0499 (5)	0.0006 (5)	−0.0004 (5)	0.0042 (4)
Cl1	0.0817 (14)	0.0688 (9)	0.0518 (9)	0.0106 (10)	−0.0023 (11)	0.0058 (9)
Cl2	0.0587 (11)	0.0678 (9)	0.0814 (11)	−0.0092 (8)	−0.0010 (11)	0.0118 (10)
Cl3	0.0703 (13)	0.0697 (9)	0.0765 (11)	0.0135 (9)	−0.0031 (11)	0.0088 (10)
O1	0.126 (6)	0.117 (4)	0.089 (3)	−0.022 (4)	0.033 (4)	0.012 (3)
O2	0.152 (7)	0.112 (4)	0.117 (4)	0.065 (5)	0.009 (4)	0.036 (3)
O3	0.215 (9)	0.108 (4)	0.093 (4)	0.054 (5)	0.044 (5)	−0.004 (3)
O4	0.128 (7)	0.259 (9)	0.104 (4)	−0.074 (7)	−0.041 (5)	0.035 (5)
N1	0.054 (4)	0.054 (3)	0.045 (3)	−0.005 (2)	0.001 (3)	−0.006 (3)
N2	0.047 (3)	0.056 (3)	0.047 (3)	0.004 (3)	0.005 (3)	−0.001 (2)
N3	0.051 (3)	0.056 (3)	0.058 (3)	−0.007 (3)	0.003 (3)	0.009 (3)
N4	0.043 (3)	0.067 (3)	0.049 (3)	0.006 (3)	−0.001 (2)	0.009 (2)
C1	0.065 (6)	0.077 (4)	0.058 (4)	0.002 (4)	−0.002 (4)	−0.004 (4)
C2	0.092 (7)	0.064 (4)	0.081 (5)	0.014 (5)	−0.005 (5)	−0.025 (4)
C3	0.076 (7)	0.055 (4)	0.099 (6)	0.010 (4)	−0.010 (5)	−0.011 (5)
C4	0.067 (6)	0.057 (4)	0.071 (4)	−0.002 (4)	−0.004 (4)	0.008 (4)
C5	0.044 (4)	0.038 (3)	0.062 (4)	−0.003 (3)	−0.007 (3)	−0.002 (3)
C6	0.043 (4)	0.050 (3)	0.049 (3)	−0.005 (3)	−0.003 (3)	0.005 (3)
C7	0.077 (6)	0.068 (4)	0.058 (4)	−0.015 (4)	−0.008 (4)	0.010 (4)
C8	0.070 (5)	0.101 (5)	0.047 (4)	−0.003 (5)	−0.001 (4)	0.006 (4)
C9	0.061 (5)	0.091 (5)	0.055 (4)	−0.013 (5)	0.008 (4)	−0.012 (4)
C10	0.056 (5)	0.064 (4)	0.060 (4)	0.001 (4)	0.001 (4)	−0.008 (3)
C11	0.054 (5)	0.068 (4)	0.075 (5)	0.000 (4)	0.002 (4)	0.001 (4)
C12	0.080 (7)	0.062 (4)	0.094 (6)	−0.015 (4)	0.017 (5)	0.007 (5)
C13	0.068 (6)	0.067 (4)	0.102 (6)	−0.008 (4)	0.014 (5)	−0.023 (5)
C14	0.068 (6)	0.067 (4)	0.075 (5)	−0.001 (4)	−0.002 (4)	−0.019 (4)
C15	0.048 (5)	0.051 (3)	0.062 (4)	0.002 (3)	−0.009 (3)	−0.009 (3)
C16	0.066 (5)	0.051 (4)	0.051 (4)	0.016 (4)	−0.017 (4)	0.003 (3)
C17	0.088 (6)	0.066 (4)	0.063 (4)	0.004 (4)	−0.018 (5)	−0.012 (4)
C18	0.122 (9)	0.084 (5)	0.049 (4)	0.002 (6)	−0.008 (5)	−0.005 (4)
C19	0.115 (8)	0.096 (6)	0.048 (4)	0.006 (6)	0.011 (4)	0.017 (4)
C20	0.079 (6)	0.097 (5)	0.060 (4)	−0.008 (5)	0.007 (4)	0.014 (4)

Geometric parameters (Å, º) top

Fe1—N2	2.087 (4)	C5—C6	1.432 (8)
Fe1—N4	2.096 (5)	C6—C7	1.385 (8)
Fe1—N1	2.121 (5)	C7—C8	1.336 (9)
Fe1—N3	2.147 (5)	C7—H7	0.9300
Fe1—Cl3	2.2074 (18)	C8—C9	1.310 (9)
Fe1—Cl2	2.220 (2)	C8—H8	0.9300
Cl1—O2	1.363 (5)	C9—C10	1.366 (8)
Cl1—O4	1.366 (7)	C9—H9	0.9300
Cl1—O3	1.371 (5)	C10—H10	0.9300
Cl1—O1	1.373 (6)	C11—C12	1.346 (11)
N1—C1	1.302 (8)	C11—H11	0.9300
N1—C5	1.332 (7)	C12—C13	1.340 (11)
N2—C6	1.306 (7)	C12—H12	0.9300
N2—C10	1.324 (7)	C13—C14	1.346 (9)
N3—C11	1.306 (8)	C13—H13	0.9300
N3—C15	1.330 (7)	C14—C15	1.358 (9)
N4—C16	1.311 (8)	C14—H14	0.9300
N4—C20	1.329 (8)	C15—C16	1.444 (9)
C1—C2	1.360 (10)	C16—C17	1.365 (8)
C1—H1	0.9300	C17—C18	1.353 (10)
C2—C3	1.362 (10)	C17—H17	0.9300
C2—H2	0.9300	C18—C19	1.344 (11)
C3—C4	1.342 (9)	C18—H18	0.9300
C3—H3	0.9300	C19—C20	1.378 (9)
C4—C5	1.350 (9)	C19—H19	0.9300
C4—H4	0.9300	C20—H20	0.9300

N2—Fe1—N4	160.23 (18)	C4—C5—C6	123.6 (6)
N2—Fe1—N1	75.96 (19)	N2—C6—C7	119.5 (6)
N4—Fe1—N1	90.98 (18)	N2—C6—C5	116.0 (5)
N2—Fe1—N3	88.34 (19)	C7—C6—C5	124.5 (6)
N4—Fe1—N3	75.4 (2)	C8—C7—C6	120.7 (7)
N1—Fe1—N3	84.2 (2)	C8—C7—H7	119.6
N2—Fe1—Cl3	97.95 (16)	C6—C7—H7	119.6
N4—Fe1—Cl3	93.40 (14)	C9—C8—C7	119.1 (7)
N1—Fe1—Cl3	171.80 (16)	C9—C8—H8	120.5
N3—Fe1—Cl3	90.20 (15)	C7—C8—H8	120.5
N2—Fe1—Cl2	94.29 (15)	C8—C9—C10	119.7 (7)
N4—Fe1—Cl2	99.84 (16)	C8—C9—H9	120.1
N1—Fe1—Cl2	86.93 (15)	C10—C9—H9	120.1
N3—Fe1—Cl2	169.85 (15)	N2—C10—C9	121.6 (6)
Cl3—Fe1—Cl2	99.13 (8)	N2—C10—H10	119.2
O2—Cl1—O4	109.4 (5)	C9—C10—H10	119.2
O2—Cl1—O3	108.0 (4)	N3—C11—C12	124.8 (7)
O4—Cl1—O3	111.0 (6)	N3—C11—H11	117.6
O2—Cl1—O1	110.7 (4)	C12—C11—H11	117.6
O4—Cl1—O1	106.7 (4)	C13—C12—C11	117.1 (8)
O3—Cl1—O1	111.0 (4)	C13—C12—H12	121.4
C1—N1—C5	119.5 (6)	C11—C12—H12	121.4
C1—N1—Fe1	125.7 (4)	C12—C13—C14	119.8 (8)
C5—N1—Fe1	114.8 (4)	C12—C13—H13	120.1
C6—N2—C10	119.3 (5)	C14—C13—H13	120.1
C6—N2—Fe1	117.1 (4)	C13—C14—C15	120.2 (7)
C10—N2—Fe1	123.5 (4)	C13—C14—H14	119.9
C11—N3—C15	117.8 (6)	C15—C14—H14	119.9
C11—N3—Fe1	127.5 (5)	N3—C15—C14	120.2 (7)
C15—N3—Fe1	114.6 (4)	N3—C15—C16	116.3 (6)
C16—N4—C20	119.2 (6)	C14—C15—C16	123.5 (6)
C16—N4—Fe1	117.6 (4)	N4—C16—C17	121.7 (7)
C20—N4—Fe1	123.0 (5)	N4—C16—C15	115.4 (5)
N1—C1—C2	122.8 (7)	C17—C16—C15	122.9 (7)
N1—C1—H1	118.6	C18—C17—C16	119.2 (7)
C2—C1—H1	118.6	C18—C17—H17	120.4
C1—C2—C3	117.5 (7)	C16—C17—H17	120.4
C1—C2—H2	121.3	C19—C18—C17	120.0 (7)
C3—C2—H2	121.3	C19—C18—H18	120.0
C4—C3—C2	119.7 (7)	C17—C18—H18	120.0
C4—C3—H3	120.1	C18—C19—C20	118.4 (8)
C2—C3—H3	120.1	C18—C19—H19	120.8
C3—C4—C5	120.1 (7)	C20—C19—H19	120.8
C3—C4—H4	119.9	N4—C20—C19	121.6 (8)
C5—C4—H4	119.9	N4—C20—H20	119.2
N1—C5—C4	120.3 (6)	C19—C20—H20	119.2
N1—C5—C6	116.1 (5)

Hydrogen-bond geometry (Å, º) top

Cg4 is the centroid of the N2,C6–C10 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2	0.93	2.52	3.140 (11)	124
C7—H7···O3ⁱ	0.93	2.55	3.239 (9)	131
C8—H8···O2ⁱⁱ	0.93	2.30	3.152 (9)	152
C13—H13···O2ⁱⁱⁱ	0.93	2.54	3.423 (10)	158
C18—H18···O4^iv	0.93	2.51	3.387 (10)	158
C10—H10···Cl3	0.93	2.71	3.308 (7)	122
C20—H20···Cl2	0.93	2.79	3.382 (7)	123
C11—H11···Cg4	0.93	2.90	3.705 (8)	146

Symmetry codes: (i) x+1/2, −y+3/2, −z; (ii) −x+3/2, −y+1, z−1/2; (iii) x+1, y, z; (iv) −x+3/2, −y+1, z+1/2.

Experimental details

Crystal data
Chemical formula	[FeCl₂(C₁₀H₈N₂)₂]ClO₄
M_r	538.57
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	295
a, b, c (Å)	10.891 (2), 11.522 (2), 16.990 (3)
V (Å³)	2132.1 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.12
Crystal size (mm)	0.34 × 0.29 × 0.24

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.702, 0.775
No. of measured, independent and observed [I > 2σ(I)] reflections	5914, 3534, 2810
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.125, 1.08
No. of reflections	3534
No. of parameters	289
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.75, −0.42
Absolute structure	Flack (1983), 1419 Friedel pairs
Absolute structure parameter	0.05 (3)

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2003), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

Cg4 is the centroid of the N2,C6–C10 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2	0.93	2.52	3.140 (11)	124
C7—H7···O3ⁱ	0.93	2.55	3.239 (9)	131
C8—H8···O2ⁱⁱ	0.93	2.30	3.152 (9)	152
C13—H13···O2ⁱⁱⁱ	0.93	2.54	3.423 (10)	158
C18—H18···O4^iv	0.93	2.51	3.387 (10)	158
C10—H10···Cl3	0.93	2.71	3.308 (7)	122
C20—H20···Cl2	0.93	2.79	3.382 (7)	123
C11—H11···Cg4	0.93	2.90	3.705 (8)	146

Symmetry codes: (i) x+1/2, −y+3/2, −z; (ii) −x+3/2, −y+1, z−1/2; (iii) x+1, y, z; (iv) −x+3/2, −y+1, z+1/2.

Acknowledgements

The author gratefully acknowledges financial support from the Natural Science Foundation of the Education Department of Shaanxi Provincial Government (09 J K844) and is grateful for support provided by the key industry problem plan of Yulin (gygg200807) and the special research projects of Yulin University (08YK17).

References

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Volume 67| Part 6| June 2011| Page m677

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