(Ferrocenylmeth­yl)trimethyl­ammonium perchlorate

Wang, Y.-C.

doi:10.1107/S1600536812002176

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page m197

doi:10.1107/S1600536812002176

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(Ferrocenylmethyl)trimethylammonium perchlorate

Ying-Chun Wang ^a ^*

^aCollege of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
^*Correspondence e-mail: wangyc33@yahoo.com.cn

(Received 8 January 2012; accepted 18 January 2012; online 21 January 2012)

The asymmetric unit of the title complex, [Fe(C₅H₅)(C₉H₁₅N)]ClO₄, contains one discrete (ferrocenylmethyl)trimethylammonium cation and one perchlorate anion. The anion is disordered over two sets of sites, with refined occupancies of 0.776 (8) and 0.224 (8). The distances from the Fe atom to the centroids of the unsubstituted and substituted cyclopentadienyl (Cp) rings are 1.650 (1) and 1.640 (1) Å, respectively. The Cp rings form a dihedral angle of 2.66 (3)°.

Related literature

For a related structure, see: Pullen et al. (1998 ). For the ferroelectric properties of related amino derivatives, see: Fu et al. (2011a ,b ,c ); Fu et al. (2007 , 2008 , 2009 ); Fu & Xiong (2008 ).

Experimental

Crystal data

[Fe(C₅H₅)(C₉H₁₅N)]ClO₄
M_r = 357.61
Monoclinic, P 2₁ /c
a = 8.5972 (17) Å
b = 13.783 (3) Å
c = 13.096 (3) Å
β = 101.23 (3)°
V = 1522.1 (6) Å³
Z = 4
Mo Kα radiation
μ = 1.18 mm⁻¹
T = 298 K
0.10 × 0.03 × 0.03 mm

Data collection

Rigaku Mercury2 diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.910, T_max = 1.000
15527 measured reflections
3479 independent reflections
2642 reflections with I > 2σ(I)
R_int = 0.062

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.148
S = 1.07
3479 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.73 e Å⁻³

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/S1600536812002176/lh5405sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812002176/lh5405Isup2.hkl

checkCIF report

Comment top

Simple organic salts containig amino cations have attracted an attention as materials which display ferroelectric-paraelectric phase transitions (Fu et al., 2011a, b and c). With the purpose of obtaining phase transition crystals of amino compounds, various amines have been studied and a series of new materials with this organic molecules have been elaborated (Fu et al. 2007, 2008, 2009; Fu & Xiong 2008). Herein we present the crystal structure of the title compound (I), which may be used as a cation in organic salts. In this study, we describe the crystal structure of this compound.

The asymmetric unit of (I) contains one discrete trimethyl(ferrocenyl)methylammonium cation and one ClO₄^- anion (Fig. 1). The anion is disordered over two sets of sites with refined occupancies 0.776 (8) and 0.224 (8). The distances from the Fe atom to the centroids of the unsubstituted and substituted cyclopentadienyl (Cp) rings are 1.650 (1) and 1.640 (1)Å , respectively. The dihedral angles between the two Cp rings are 2.66 (3)°. The two cyclopentadienyl rings of the ferrocenyl group are almost eclipsed with the (C—Cg1—Cg2—C) torsion angles in the two Cp rings in the range of 3.67 (3) to 4.74 (3)°. For a comparison of bond lengths and angles, see those in the related structure (Pullen et al., 1998).

Related literature top

For a related structure, see: Pullen et al. (1998). For the ferroelectric properties of related amino derivatives, see: Fu et al. (2011a,b,c); Fu et al. (2007, 2008, 2009); Fu & Xiong (2008).

Experimental top

A mixture of commercial trimethyl(ferrocenyl)methylamine (0.4 mmol) and HClO₄ (0.4 mmol) were dissolved in EtOH/distilled water (1:1 v/v) solvent. The solution was slowly evaporated in air affording red block-shaped crystals of the title compound suitable for X-ray analysis.

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. A view of the title compound with displacement ellipsoids drawn at the 30% probability level. The disorder is not shown.

(Ferrocenylmethyl)trimethylammonium perchlorate top

Crystal data top

[Fe(C₅H₅)(C₉H₁₅N)]ClO₄	F(000) = 744
M_r = 357.61	D_x = 1.561 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3479 reflections
a = 8.5972 (17) Å	θ = 3.0–27.5°
b = 13.783 (3) Å	µ = 1.18 mm⁻¹
c = 13.096 (3) Å	T = 298 K
β = 101.23 (3)°	Block, red
V = 1522.1 (6) Å³	0.10 × 0.03 × 0.03 mm
Z = 4

Data collection top

Rigaku Mercury2 diffractometer	3479 independent reflections
Radiation source: fine-focus sealed tube	2642 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.062
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.5°, θ_min = 3.0°
CCD profile fitting scans	h = −11→11
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −17→17
T_min = 0.910, T_max = 1.000	l = −16→17
15527 measured reflections

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.148	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0595P)² + 2.0318P] where P = (F_o² + 2F_c²)/3
3479 reflections	(Δ/σ)_max < 0.001
218 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.73 e Å⁻³

Crystal data top

[Fe(C₅H₅)(C₉H₁₅N)]ClO₄	V = 1522.1 (6) Å³
M_r = 357.61	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.5972 (17) Å	µ = 1.18 mm⁻¹
b = 13.783 (3) Å	T = 298 K
c = 13.096 (3) Å	0.10 × 0.03 × 0.03 mm
β = 101.23 (3)°

Data collection top

Rigaku Mercury2 diffractometer	3479 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	2642 reflections with I > 2σ(I)
T_min = 0.910, T_max = 1.000	R_int = 0.062
15527 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.148	H-atom parameters constrained
S = 1.07	Δρ_max = 0.32 e Å⁻³
3479 reflections	Δρ_min = −0.73 e Å⁻³
218 parameters

Special details top

Experimental. The dielectric constant of title compound as a function of temperature indicates that the permittivity is basically temperature-independent, suggesting that this compound should be not a real ferroelectrics or there may be no distinct phase transition occurred within the measured temperature range. Similarly, below the melting point (411 K) of the compound, the dielectric constant as a function of temperature also goes smoothly, and there is no dielectric anomaly observed (dielectric constant ranging from 4.4 to 9.5).

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.66928 (6)	0.67531 (3)	0.46111 (4)	0.03474 (18)
N1	0.2467 (4)	0.8607 (2)	0.3523 (2)	0.0387 (7)
C1	0.6435 (5)	0.6059 (3)	0.3215 (3)	0.0439 (9)
H1A	0.5675	0.6231	0.2581	0.053*
C2	0.6154 (5)	0.5411 (3)	0.3991 (3)	0.0463 (9)
H2A	0.5169	0.5052	0.3989	0.056*
C3	0.7542 (6)	0.5370 (3)	0.4773 (4)	0.0528 (11)
H3A	0.7694	0.4977	0.5408	0.063*
C4	0.8680 (5)	0.5997 (3)	0.4467 (3)	0.0516 (10)
H4A	0.9756	0.6117	0.4857	0.062*
C5	0.7992 (5)	0.6413 (3)	0.3501 (3)	0.0469 (9)
H5A	0.8503	0.6877	0.3105	0.056*
C6	0.4993 (5)	0.7790 (2)	0.4457 (3)	0.0371 (8)
C7	0.6527 (5)	0.8227 (3)	0.4722 (3)	0.0476 (10)
H7A	0.6967	0.8702	0.4299	0.057*
C8	0.7317 (6)	0.7840 (3)	0.5682 (4)	0.0568 (11)
H8A	0.8396	0.7999	0.6041	0.068*
C9	0.6286 (6)	0.7178 (3)	0.6028 (3)	0.0577 (12)
H9A	0.6532	0.6796	0.6670	0.069*
C10	0.4849 (5)	0.7132 (3)	0.5283 (3)	0.0455 (9)
H10A	0.3925	0.6730	0.5327	0.055*
C11	0.3848 (5)	0.7937 (3)	0.3457 (3)	0.0415 (8)
H11A	0.3429	0.7310	0.3203	0.050*
H11B	0.4419	0.8200	0.2949	0.050*
C12	0.3026 (6)	0.9568 (3)	0.3968 (4)	0.0570 (11)
H12A	0.3564	0.9487	0.4677	0.085*
H12B	0.2133	0.9991	0.3944	0.085*
H12C	0.3741	0.9845	0.3569	0.085*
C13	0.1414 (5)	0.8167 (3)	0.4173 (4)	0.0587 (11)
H13A	0.2010	0.8051	0.4862	0.088*
H13B	0.1000	0.7563	0.3869	0.088*
H13C	0.0554	0.8601	0.4208	0.088*
C14	0.1527 (6)	0.8749 (4)	0.2435 (3)	0.0603 (12)
H14A	0.0651	0.9177	0.2455	0.091*
H14B	0.1134	0.8134	0.2152	0.091*
H14C	0.2197	0.9028	0.2006	0.091*
Cl2	0.18301 (16)	0.55643 (10)	0.19867 (10)	0.0700 (4)	0.776 (8)
O1'	0.1752 (13)	0.5939 (6)	0.2902 (6)	0.155 (4)	0.776 (8)
O2'	0.2997 (11)	0.6113 (8)	0.1573 (5)	0.126 (4)	0.776 (8)
O3'	0.0584 (9)	0.5454 (9)	0.1175 (7)	0.176 (5)	0.776 (8)
O4'	0.2388 (19)	0.4651 (7)	0.2210 (8)	0.226 (6)	0.776 (8)
Cl1	0.18301 (16)	0.55643 (10)	0.19867 (10)	0.0700 (4)	0.224 (8)
O1	0.109 (3)	0.6459 (15)	0.174 (2)	0.120 (10)	0.224 (8)
O2	0.318 (2)	0.547 (2)	0.155 (2)	0.100 (11)	0.224 (8)
O4	0.204 (2)	0.5450 (16)	0.2919 (16)	0.0700 (4)	0.224 (8)
O3	0.107 (3)	0.4943 (15)	0.1361 (16)	0.0700 (4)	0.224 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.0385 (3)	0.0296 (3)	0.0361 (3)	0.0032 (2)	0.0074 (2)	0.0004 (2)
N1	0.0406 (17)	0.0310 (15)	0.0446 (17)	0.0015 (13)	0.0084 (14)	0.0006 (13)
C1	0.049 (2)	0.042 (2)	0.042 (2)	0.0069 (17)	0.0115 (17)	−0.0069 (16)
C2	0.050 (2)	0.0316 (19)	0.062 (3)	0.0002 (16)	0.022 (2)	−0.0085 (17)
C3	0.068 (3)	0.036 (2)	0.059 (3)	0.020 (2)	0.024 (2)	0.0103 (18)
C4	0.040 (2)	0.057 (3)	0.057 (2)	0.0133 (19)	0.0088 (19)	0.002 (2)
C5	0.043 (2)	0.052 (2)	0.051 (2)	0.0006 (18)	0.0206 (19)	0.0021 (19)
C6	0.045 (2)	0.0279 (18)	0.0401 (19)	0.0057 (15)	0.0118 (16)	−0.0019 (14)
C7	0.052 (2)	0.0315 (19)	0.059 (3)	−0.0043 (17)	0.008 (2)	−0.0072 (18)
C8	0.059 (3)	0.048 (2)	0.057 (3)	0.003 (2)	−0.006 (2)	−0.017 (2)
C9	0.080 (3)	0.057 (3)	0.035 (2)	0.021 (2)	0.008 (2)	−0.0040 (19)
C10	0.057 (2)	0.039 (2)	0.045 (2)	0.0123 (18)	0.0210 (19)	0.0012 (17)
C11	0.045 (2)	0.0354 (19)	0.045 (2)	0.0048 (16)	0.0113 (17)	−0.0035 (16)
C12	0.063 (3)	0.031 (2)	0.073 (3)	0.0022 (19)	0.003 (2)	−0.0063 (19)
C13	0.048 (2)	0.064 (3)	0.068 (3)	−0.003 (2)	0.020 (2)	0.005 (2)
C14	0.059 (3)	0.063 (3)	0.053 (3)	0.009 (2)	−0.003 (2)	0.002 (2)
Cl2	0.0726 (8)	0.0714 (9)	0.0628 (7)	−0.0219 (6)	0.0057 (6)	−0.0068 (6)
O1'	0.283 (11)	0.088 (5)	0.131 (6)	−0.044 (6)	0.131 (7)	−0.052 (5)
O2'	0.124 (7)	0.192 (9)	0.060 (4)	−0.107 (7)	0.012 (4)	0.007 (5)
O3'	0.089 (5)	0.237 (12)	0.166 (8)	−0.068 (6)	−0.063 (5)	0.090 (7)
O4'	0.406 (18)	0.094 (6)	0.182 (9)	0.117 (9)	0.066 (10)	0.035 (6)
Cl1	0.0726 (8)	0.0714 (9)	0.0628 (7)	−0.0219 (6)	0.0057 (6)	−0.0068 (6)
O1	0.125 (19)	0.056 (11)	0.16 (2)	0.058 (12)	−0.015 (16)	−0.007 (13)
O2	0.017 (7)	0.15 (2)	0.14 (2)	−0.028 (11)	0.024 (9)	−0.07 (2)
O4	0.0726 (8)	0.0714 (9)	0.0628 (7)	−0.0219 (6)	0.0057 (6)	−0.0068 (6)
O3	0.0726 (8)	0.0714 (9)	0.0628 (7)	−0.0219 (6)	0.0057 (6)	−0.0068 (6)

Geometric parameters (Å, º) top

Fe1—C10	2.025 (4)	C6—C10	1.435 (5)
Fe1—C6	2.026 (4)	C6—C11	1.491 (5)
Fe1—C1	2.037 (4)	C7—C8	1.412 (6)
Fe1—C2	2.037 (4)	C7—H7A	0.9800
Fe1—C3	2.037 (4)	C8—C9	1.407 (7)
Fe1—C9	2.040 (4)	C8—H8A	0.9800
Fe1—C4	2.041 (4)	C9—C10	1.418 (6)
Fe1—C7	2.044 (4)	C9—H9A	0.9800
Fe1—C8	2.051 (4)	C10—H10A	0.9800
Fe1—C5	2.053 (4)	C11—H11A	0.9700
N1—C13	1.488 (5)	C11—H11B	0.9700
N1—C12	1.489 (5)	C12—H12A	0.9600
N1—C14	1.507 (5)	C12—H12B	0.9600
N1—C11	1.520 (5)	C12—H12C	0.9600
C1—C5	1.405 (6)	C13—H13A	0.9600
C1—C2	1.408 (6)	C13—H13B	0.9600
C1—H1A	0.9800	C13—H13C	0.9600
C2—C3	1.415 (6)	C14—H14A	0.9600
C2—H2A	0.9800	C14—H14B	0.9600
C3—C4	1.420 (6)	C14—H14C	0.9600
C3—H3A	0.9800	Cl2—O1'	1.319 (6)
C4—C5	1.410 (6)	Cl2—O4'	1.358 (7)
C4—H4A	0.9800	Cl2—O3'	1.363 (7)
C5—H5A	0.9800	Cl2—O2'	1.443 (6)
C6—C7	1.430 (5)

C10—Fe1—C6	41.48 (15)	C3—C4—Fe1	69.5 (2)
C10—Fe1—C1	123.60 (17)	C5—C4—H4A	126.0
C6—Fe1—C1	106.95 (16)	C3—C4—H4A	126.0
C10—Fe1—C2	105.73 (17)	Fe1—C4—H4A	126.0
C6—Fe1—C2	119.82 (16)	C1—C5—C4	108.0 (4)
C1—Fe1—C2	40.45 (16)	C1—C5—Fe1	69.3 (2)
C10—Fe1—C3	119.43 (17)	C4—C5—Fe1	69.4 (2)
C6—Fe1—C3	155.14 (18)	C1—C5—H5A	126.0
C1—Fe1—C3	68.17 (17)	C4—C5—H5A	126.0
C2—Fe1—C3	40.63 (18)	Fe1—C5—H5A	126.0
C10—Fe1—C9	40.84 (18)	C7—C6—C10	107.1 (4)
C6—Fe1—C9	68.88 (16)	C7—C6—C11	125.1 (3)
C1—Fe1—C9	160.6 (2)	C10—C6—C11	127.5 (4)
C2—Fe1—C9	123.89 (19)	C7—C6—Fe1	70.1 (2)
C3—Fe1—C9	107.20 (18)	C10—C6—Fe1	69.2 (2)
C10—Fe1—C4	155.77 (17)	C11—C6—Fe1	121.6 (2)
C6—Fe1—C4	162.09 (17)	C8—C7—C6	108.5 (4)
C1—Fe1—C4	67.90 (17)	C8—C7—Fe1	70.1 (2)
C2—Fe1—C4	68.21 (17)	C6—C7—Fe1	68.8 (2)
C3—Fe1—C4	40.75 (18)	C8—C7—H7A	125.7
C9—Fe1—C4	121.73 (18)	C6—C7—H7A	125.7
C10—Fe1—C7	68.97 (17)	Fe1—C7—H7A	125.7
C6—Fe1—C7	41.13 (15)	C9—C8—C7	107.9 (4)
C1—Fe1—C7	122.26 (17)	C9—C8—Fe1	69.5 (2)
C2—Fe1—C7	156.55 (17)	C7—C8—Fe1	69.6 (2)
C3—Fe1—C7	162.02 (18)	C9—C8—H8A	126.0
C9—Fe1—C7	67.86 (18)	C7—C8—H8A	126.0
C4—Fe1—C7	125.84 (18)	Fe1—C8—H8A	126.0
C10—Fe1—C8	68.72 (19)	C8—C9—C10	109.0 (4)
C6—Fe1—C8	68.92 (17)	C8—C9—Fe1	70.3 (3)
C1—Fe1—C8	157.69 (19)	C10—C9—Fe1	69.0 (2)
C2—Fe1—C8	160.89 (19)	C8—C9—H9A	125.5
C3—Fe1—C8	124.85 (19)	C10—C9—H9A	125.5
C9—Fe1—C8	40.2 (2)	Fe1—C9—H9A	125.5
C4—Fe1—C8	108.92 (19)	C9—C10—C6	107.4 (4)
C7—Fe1—C8	40.35 (17)	C9—C10—Fe1	70.1 (2)
C10—Fe1—C5	161.13 (17)	C6—C10—Fe1	69.3 (2)
C6—Fe1—C5	124.89 (16)	C9—C10—H10A	126.3
C1—Fe1—C5	40.19 (16)	C6—C10—H10A	126.3
C2—Fe1—C5	67.84 (17)	Fe1—C10—H10A	126.3
C3—Fe1—C5	68.07 (17)	C6—C11—N1	115.0 (3)
C9—Fe1—C5	157.41 (19)	C6—C11—H11A	108.5
C4—Fe1—C5	40.28 (17)	N1—C11—H11A	108.5
C7—Fe1—C5	109.43 (18)	C6—C11—H11B	108.5
C8—Fe1—C5	123.05 (19)	N1—C11—H11B	108.5
C13—N1—C12	108.9 (3)	H11A—C11—H11B	107.5
C13—N1—C14	108.7 (3)	N1—C12—H12A	109.5
C12—N1—C14	109.1 (3)	N1—C12—H12B	109.5
C13—N1—C11	110.7 (3)	H12A—C12—H12B	109.5
C12—N1—C11	111.5 (3)	N1—C12—H12C	109.5
C14—N1—C11	107.9 (3)	H12A—C12—H12C	109.5
C5—C1—C2	108.4 (4)	H12B—C12—H12C	109.5
C5—C1—Fe1	70.5 (2)	N1—C13—H13A	109.5
C2—C1—Fe1	69.8 (2)	N1—C13—H13B	109.5
C5—C1—H1A	125.8	H13A—C13—H13B	109.5
C2—C1—H1A	125.8	N1—C13—H13C	109.5
Fe1—C1—H1A	125.8	H13A—C13—H13C	109.5
C1—C2—C3	108.0 (4)	H13B—C13—H13C	109.5
C1—C2—Fe1	69.7 (2)	N1—C14—H14A	109.5
C3—C2—Fe1	69.7 (2)	N1—C14—H14B	109.5
C1—C2—H2A	126.0	H14A—C14—H14B	109.5
C3—C2—H2A	126.0	N1—C14—H14C	109.5
Fe1—C2—H2A	126.0	H14A—C14—H14C	109.5
C2—C3—C4	107.6 (4)	H14B—C14—H14C	109.5
C2—C3—Fe1	69.7 (2)	O1'—Cl2—O4'	104.2 (6)
C4—C3—Fe1	69.8 (2)	O1'—Cl2—O3'	125.5 (8)
C2—C3—H3A	126.2	O4'—Cl2—O3'	104.8 (8)
C4—C3—H3A	126.2	O1'—Cl2—O2'	107.3 (5)
Fe1—C3—H3A	126.2	O4'—Cl2—O2'	108.9 (8)
C5—C4—C3	108.0 (4)	O3'—Cl2—O2'	105.3 (5)
C5—C4—Fe1	70.3 (2)

C10—Fe1—C1—C5	166.9 (2)	C3—Fe1—C6—C10	47.4 (5)
C6—Fe1—C1—C5	124.5 (2)	C9—Fe1—C6—C10	−38.0 (3)
C2—Fe1—C1—C5	−119.2 (4)	C4—Fe1—C6—C10	−167.7 (5)
C3—Fe1—C1—C5	−81.4 (3)	C7—Fe1—C6—C10	−118.1 (3)
C9—Fe1—C1—C5	−161.1 (5)	C8—Fe1—C6—C10	−81.3 (3)
C4—Fe1—C1—C5	−37.3 (3)	C5—Fe1—C6—C10	162.4 (2)
C7—Fe1—C1—C5	82.1 (3)	C10—Fe1—C6—C11	−122.1 (4)
C8—Fe1—C1—C5	48.8 (5)	C1—Fe1—C6—C11	−0.2 (3)
C10—Fe1—C1—C2	−73.9 (3)	C2—Fe1—C6—C11	−42.3 (4)
C6—Fe1—C1—C2	−116.3 (2)	C3—Fe1—C6—C11	−74.7 (5)
C3—Fe1—C1—C2	37.8 (3)	C9—Fe1—C6—C11	−160.2 (4)
C9—Fe1—C1—C2	−41.9 (6)	C4—Fe1—C6—C11	70.2 (6)
C4—Fe1—C1—C2	81.9 (3)	C7—Fe1—C6—C11	119.8 (4)
C7—Fe1—C1—C2	−158.7 (2)	C8—Fe1—C6—C11	156.6 (4)
C8—Fe1—C1—C2	168.0 (4)	C5—Fe1—C6—C11	40.2 (4)
C5—Fe1—C1—C2	119.2 (4)	C10—C6—C7—C8	0.7 (4)
C5—C1—C2—C3	0.7 (4)	C11—C6—C7—C8	−174.1 (4)
Fe1—C1—C2—C3	−59.4 (3)	Fe1—C6—C7—C8	−58.9 (3)
C5—C1—C2—Fe1	60.2 (3)	C10—C6—C7—Fe1	59.6 (2)
C10—Fe1—C2—C1	123.8 (2)	C11—C6—C7—Fe1	−115.2 (3)
C6—Fe1—C2—C1	81.1 (3)	C10—Fe1—C7—C8	81.5 (3)
C3—Fe1—C2—C1	−119.1 (4)	C6—Fe1—C7—C8	120.2 (4)
C9—Fe1—C2—C1	164.5 (2)	C1—Fe1—C7—C8	−161.2 (3)
C4—Fe1—C2—C1	−81.0 (3)	C2—Fe1—C7—C8	162.5 (4)
C7—Fe1—C2—C1	50.5 (5)	C3—Fe1—C7—C8	−39.9 (7)
C8—Fe1—C2—C1	−166.0 (5)	C9—Fe1—C7—C8	37.4 (3)
C5—Fe1—C2—C1	−37.5 (2)	C4—Fe1—C7—C8	−76.6 (3)
C10—Fe1—C2—C3	−117.1 (3)	C5—Fe1—C7—C8	−118.6 (3)
C6—Fe1—C2—C3	−159.7 (2)	C10—Fe1—C7—C6	−38.7 (2)
C1—Fe1—C2—C3	119.1 (4)	C1—Fe1—C7—C6	78.5 (3)
C9—Fe1—C2—C3	−76.4 (3)	C2—Fe1—C7—C6	42.3 (5)
C4—Fe1—C2—C3	38.1 (3)	C3—Fe1—C7—C6	−160.1 (5)
C7—Fe1—C2—C3	169.6 (4)	C9—Fe1—C7—C6	−82.8 (3)
C8—Fe1—C2—C3	−46.9 (6)	C4—Fe1—C7—C6	163.2 (2)
C5—Fe1—C2—C3	81.7 (3)	C8—Fe1—C7—C6	−120.2 (4)
C1—C2—C3—C4	−0.3 (4)	C5—Fe1—C7—C6	121.2 (2)
Fe1—C2—C3—C4	−59.7 (3)	C6—C7—C8—C9	−0.9 (5)
C1—C2—C3—Fe1	59.5 (3)	Fe1—C7—C8—C9	−59.1 (3)
C10—Fe1—C3—C2	79.7 (3)	C6—C7—C8—Fe1	58.1 (3)
C6—Fe1—C3—C2	45.6 (5)	C10—Fe1—C8—C9	37.2 (3)
C1—Fe1—C3—C2	−37.6 (2)	C6—Fe1—C8—C9	81.8 (3)
C9—Fe1—C3—C2	122.4 (3)	C1—Fe1—C8—C9	165.2 (4)
C4—Fe1—C3—C2	−118.6 (4)	C2—Fe1—C8—C9	−39.2 (7)
C7—Fe1—C3—C2	−166.6 (5)	C3—Fe1—C8—C9	−74.6 (3)
C8—Fe1—C3—C2	163.1 (3)	C4—Fe1—C8—C9	−117.1 (3)
C5—Fe1—C3—C2	−81.1 (3)	C7—Fe1—C8—C9	119.3 (4)
C10—Fe1—C3—C4	−161.7 (3)	C5—Fe1—C8—C9	−159.5 (3)
C6—Fe1—C3—C4	164.3 (3)	C10—Fe1—C8—C7	−82.2 (3)
C1—Fe1—C3—C4	81.0 (3)	C6—Fe1—C8—C7	−37.5 (2)
C2—Fe1—C3—C4	118.6 (4)	C1—Fe1—C8—C7	45.8 (6)
C9—Fe1—C3—C4	−119.0 (3)	C2—Fe1—C8—C7	−158.6 (5)
C7—Fe1—C3—C4	−47.9 (7)	C3—Fe1—C8—C7	166.1 (3)
C8—Fe1—C3—C4	−78.3 (3)	C9—Fe1—C8—C7	−119.3 (4)
C5—Fe1—C3—C4	37.6 (3)	C4—Fe1—C8—C7	123.5 (3)
C2—C3—C4—C5	−0.3 (5)	C5—Fe1—C8—C7	81.2 (3)
Fe1—C3—C4—C5	−60.0 (3)	C7—C8—C9—C10	0.9 (5)
C2—C3—C4—Fe1	59.7 (3)	Fe1—C8—C9—C10	−58.3 (3)
C10—Fe1—C4—C5	160.8 (4)	C7—C8—C9—Fe1	59.2 (3)
C6—Fe1—C4—C5	−39.3 (6)	C10—Fe1—C9—C8	−120.5 (4)
C1—Fe1—C4—C5	37.2 (3)	C6—Fe1—C9—C8	−81.9 (3)
C2—Fe1—C4—C5	81.0 (3)	C1—Fe1—C9—C8	−163.0 (5)
C3—Fe1—C4—C5	119.0 (4)	C2—Fe1—C9—C8	165.6 (3)
C9—Fe1—C4—C5	−161.7 (3)	C3—Fe1—C9—C8	124.1 (3)
C7—Fe1—C4—C5	−77.4 (3)	C4—Fe1—C9—C8	81.9 (3)
C8—Fe1—C4—C5	−119.2 (3)	C7—Fe1—C9—C8	−37.5 (3)
C10—Fe1—C4—C3	41.8 (6)	C5—Fe1—C9—C8	50.0 (6)
C6—Fe1—C4—C3	−158.3 (5)	C6—Fe1—C9—C10	38.6 (2)
C1—Fe1—C4—C3	−81.7 (3)	C1—Fe1—C9—C10	−42.4 (6)
C2—Fe1—C4—C3	−38.0 (3)	C2—Fe1—C9—C10	−73.9 (3)
C9—Fe1—C4—C3	79.3 (3)	C3—Fe1—C9—C10	−115.4 (3)
C7—Fe1—C4—C3	163.6 (3)	C4—Fe1—C9—C10	−157.5 (3)
C8—Fe1—C4—C3	121.9 (3)	C7—Fe1—C9—C10	83.0 (3)
C5—Fe1—C4—C3	−119.0 (4)	C8—Fe1—C9—C10	120.5 (4)
C2—C1—C5—C4	−0.9 (5)	C5—Fe1—C9—C10	170.5 (4)
Fe1—C1—C5—C4	58.8 (3)	C8—C9—C10—C6	−0.4 (5)
C2—C1—C5—Fe1	−59.7 (3)	Fe1—C9—C10—C6	−59.5 (3)
C3—C4—C5—C1	0.8 (5)	C8—C9—C10—Fe1	59.1 (3)
Fe1—C4—C5—C1	−58.7 (3)	C7—C6—C10—C9	−0.1 (4)
C3—C4—C5—Fe1	59.5 (3)	C11—C6—C10—C9	174.5 (3)
C10—Fe1—C5—C1	−35.7 (6)	Fe1—C6—C10—C9	60.0 (3)
C6—Fe1—C5—C1	−74.1 (3)	C7—C6—C10—Fe1	−60.2 (3)
C2—Fe1—C5—C1	37.7 (2)	C11—C6—C10—Fe1	114.5 (4)
C3—Fe1—C5—C1	81.7 (3)	C6—Fe1—C10—C9	−118.5 (4)
C9—Fe1—C5—C1	163.7 (4)	C1—Fe1—C10—C9	164.4 (3)
C4—Fe1—C5—C1	119.7 (4)	C2—Fe1—C10—C9	124.0 (3)
C7—Fe1—C5—C1	−117.4 (3)	C3—Fe1—C10—C9	82.3 (3)
C8—Fe1—C5—C1	−160.1 (2)	C4—Fe1—C10—C9	52.3 (5)
C10—Fe1—C5—C4	−155.3 (5)	C7—Fe1—C10—C9	−80.1 (3)
C6—Fe1—C5—C4	166.3 (2)	C8—Fe1—C10—C9	−36.7 (3)
C1—Fe1—C5—C4	−119.7 (4)	C5—Fe1—C10—C9	−168.7 (5)
C2—Fe1—C5—C4	−82.0 (3)	C1—Fe1—C10—C6	−77.1 (3)
C3—Fe1—C5—C4	−38.0 (3)	C2—Fe1—C10—C6	−117.5 (2)
C9—Fe1—C5—C4	44.1 (6)	C3—Fe1—C10—C6	−159.2 (2)
C7—Fe1—C5—C4	123.0 (3)	C9—Fe1—C10—C6	118.5 (4)
C8—Fe1—C5—C4	80.2 (3)	C4—Fe1—C10—C6	170.8 (4)
C10—Fe1—C6—C7	118.1 (3)	C7—Fe1—C10—C6	38.4 (2)
C1—Fe1—C6—C7	−120.0 (2)	C8—Fe1—C10—C6	81.8 (3)
C2—Fe1—C6—C7	−162.0 (2)	C5—Fe1—C10—C6	−50.3 (6)
C3—Fe1—C6—C7	165.5 (4)	C7—C6—C11—N1	−104.2 (4)
C9—Fe1—C6—C7	80.1 (3)	C10—C6—C11—N1	82.1 (5)
C4—Fe1—C6—C7	−49.6 (6)	Fe1—C6—C11—N1	169.0 (2)
C8—Fe1—C6—C7	36.8 (3)	C13—N1—C11—C6	−66.6 (4)
C5—Fe1—C6—C7	−79.5 (3)	C12—N1—C11—C6	54.9 (4)
C1—Fe1—C6—C10	121.9 (3)	C14—N1—C11—C6	174.6 (3)
C2—Fe1—C6—C10	79.8 (3)

Experimental details

Crystal data
Chemical formula	[Fe(C₅H₅)(C₉H₁₅N)]ClO₄
M_r	357.61
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	8.5972 (17), 13.783 (3), 13.096 (3)
β (°)	101.23 (3)
V (Å³)	1522.1 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.18
Crystal size (mm)	0.10 × 0.03 × 0.03

Data collection
Diffractometer	Rigaku Mercury2 diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.910, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	15527, 3479, 2642
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.148, 1.07
No. of reflections	3479
No. of parameters	218
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.73

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

Acknowledgements

This work was supported by the Doctoral Foundation of Southeast University, China.

References

Fu, D.-W., Ge, J.-Z., Dai, J., Ye, H.-Y. & Qu, Z.-R. (2009). Inorg. Chem. Commun. 12, 994–997. Web of Science CSD CrossRef CAS Google Scholar
Fu, D.-W., Song, Y.-M., Wang, G.-X., Ye, Q., Xiong, R.-G., Akutagawa, T., Nakamura, T., Chan, P. W. H. & Huang, S. P. D. (2007). J. Am. Chem. Soc. 129, 5346–5347. Web of Science CSD CrossRef PubMed CAS Google Scholar
Fu, D.-W. & Xiong, R.-G. (2008). Dalton Trans. pp. 3946–3948. Web of Science CSD CrossRef Google Scholar
Fu, D.-W., Zhang, W., Cai, H.-L., Ge, J.-Z., Zhang, Y. & Xiong, R.-G. (2011c). Adv. Mater. 23, 5658–5662. Web of Science CSD CrossRef CAS PubMed Google Scholar
Fu, D.-W., Zhang, W., Cai, H.-L., Zhang, Y., Ge, J.-Z., Xiong, R.-G. & Huang, S. P. D. (2011a). J. Am. Chem. Soc. 133, 12780–12786. Web of Science CSD CrossRef CAS PubMed Google Scholar
Fu, D.-W., Zhang, W., Cai, H.-L., Zhang, Y., Ge, J.-Z., Xiong, R.-G., Huang, S. P. D. & Nakamura, T. (2011b). Angew. Chem. Int. Ed. 50, 11947–11951. Web of Science CSD CrossRef CAS Google Scholar
Fu, D.-W., Zhang, W. & Xiong, R.-G. (2008). Cryst. Growth Des. 8, 3461–3464. Web of Science CSD CrossRef CAS Google Scholar
Pullen, A. E., Faulmann, C., Pokhodnya, P. & Tokumoto, M. (1998). Inorg. Chem. 37, 6714–6720. Web of Science CSD CrossRef PubMed CAS 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