[N,N,N′,N′-Tetra­kis(benzimidazol-2-ylmeth­yl)cyclo­hexane-1,2-trans-diamine]­iron(II) bis­(perchlorate) methanol solvate

Wu, G.-L.; Ou, C.-P.; Wang, F.; Zhang, J.-M.; Lan, S.-M.

doi:10.1107/S1600536811011810

metal-organic compounds

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Volume 67| Part 5| May 2011| Page m531

doi:10.1107/S1600536811011810

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[N,N,N′,N′-Tetrakis(benzimidazol-2-ylmethyl)cyclohexane-1,2-trans-diamine]iron(II) bis(perchlorate) methanol solvate

Gui-Ling Wu,^a Chun-Ping Ou,^a Feng Wang,^a Jian-Ming Zhang ^a and She-Min Lan ^a ^*

^aKey Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, People's Republic of China
^*Correspondence e-mail: lanshemin@163.com

(Received 19 March 2011; accepted 30 March 2011; online 7 April 2011)

In the title compound, [Fe(C₃₈H₃₈N₁₀)](ClO₄)₂·CH₃OH, the Fe^II atom has a distorted octahedral coordination environment with four benzimidazol N atoms and two amino N atoms from an N,N,N′,N′-tetrakis(benzimidazol-2-ylmethyl)cyclohexane-1,2-trans-diamine ligand. The uncoordinated solvent methanol molecule is hydrogen bonded to an O atom of a perchlorate anion. One of the perchlorate anions is disordered over two sets of sites with occupancy factors of 0.539 (14) and 0.461 (14). N—H⋯O and C—H⋯O hydrogen bonds, as well as π–π stacking interactions between the imidazol rings and between the imidazol and benzene rings [centroid–centroid distances = 3.714 (2) and 3.705 (2) Å] give rise to a three-dimensional network.

Related literature

For model systems containing pyrazole chelates and related groups, see: Main (1992 ). For iron complexes with N,N,N′,N′-tetrakis(2-benzimidazolylmethyl)cyclohexane-1,2-trans-diamine, see: Mei et al. (2010 ); Zhao et al. (2005 ). For the synthesis of the ligand, see: Hendriks et al. (1982 ).

Experimental

Crystal data

[Fe(C₃₈H₃₈N₁₀)](ClO₄)₂·CH₄O
M_r = 921.58
Monoclinic, P 2₁ /n
a = 14.3867 (6) Å
b = 15.9145 (6) Å
c = 18.8218 (8) Å
β = 103.175 (1)°
V = 4196.0 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.55 mm⁻¹
T = 298 K
0.30 × 0.16 × 0.10 mm

Data collection

Bruker APEX CCD diffractometer
21311 measured reflections
7369 independent reflections
5765 reflections with I > 2σ(I)
R_int = 0.083

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.176
S = 1.07
7369 reflections
612 parameters
10 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.57 e Å⁻³
Δρ_min = −0.53 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4A⋯O1ⁱ	0.86	2.10	2.952 (6)	171
N6—H6A⋯O6′ⁱⁱ	0.86	2.02	2.852 (15)	162
N6—H6A⋯O6ⁱⁱ	0.86	2.13	2.955 (16)	162
N8—H8A⋯O1S	0.86	1.94	2.790 (5)	170
N10—H10A⋯O7′ⁱⁱⁱ	0.86	2.04	2.896 (10)	176
N10—H10A⋯O8ⁱⁱⁱ	0.86	2.01	2.787 (12)	150
O1S—H1S⋯O3^iv	0.96	1.88	2.813 (6)	166
C7—H7B⋯O4ⁱ	0.94 (4)	2.34 (4)	3.202 (6)	152 (3)
C23—H23A⋯O2^iv	0.97	2.40	3.318 (6)	158
Symmetry codes: (i) -x+1, -y+1, -z; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) -x+1, -y+1, -z+1; (iv) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811011810/hy2418sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811011810/hy2418Isup2.hkl

checkCIF report

Comment top

N,N,N',N'-Tetrakis(2-benzimidazolymethyl) cyclohexane-1,2-trans-diamine (ctb) is a benzimidazole-rich ligand, which has the advantage that the basicity of the coordinating group approximates that of histidine (histidine: pKb = 7.96; benzimidazole: pKb = 8.47; Main, 1992). The metal iron(III) and iron(II) can ligated by the ctb ligand, modeling the activities of lipoxygenase (Mei et al., 2010; Zhao et al., 2005). In a continuation of this work, herein we report the synthesis and structure of the title complex.

In the title compound, the Fe^II atom has a distorted octahedral coordination environment with four benzimidazol (bzim) N atoms and two amino N atoms from a ctb ligand (Fig. 1). The two trans-tertiary amine N atoms are significantly farther away from the Fe^II atom than the four bzim N atoms [average Fe—N_amine = 2.325 (3), Fe—N_bzim = 2.128 (3) Å]. As shown in Fig. 2, The uncoordinated solvent methanol molecule is hydrogen bonded to an O atom of a perchlorate anion. N—H···O and C—H···O hydrogen bonds, as well as π–π stacking interactions between the imidazol rings and between the imidazol and benzene rings [centroid–centroid distances = 3.714 (2) and 3.705 (2) Å] give rise to a three-dimensional network.

Related literature top

For model systems containing pyrazole chelates and related groups, see: Main (1992). For iron complexes with N,N,N',N'-tetrakis(2-benzimidazolylmethyl) cyclohexane-1,2-trans-diamine, see: Mei et al. (2010); Zhao et al. (2005). For the synthesis of the ligand, see: Hendriks et al. (1982).

Experimental top

All reagents and solvents were used as obtained without further purification. The ctb ligand was prepared according to literature methods (Hendriks et al., 1982). Equimolar amounts of ctb (63.4 mg, 0.10 mmol) and Fe(ClO₄)₂.6H₂O (36.3 mg, 0.10 mmol) were dissolved in 25 ml MeOH, and the solution was stirred for 10 min. After filtration, colorless crystals of the title compound (yield: 79 mg, 85% ) were obtained by diffusion of diethyl ether into the filtrate after one week under Ar atmosphere.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity.
	Fig. 2. Crystal packing of the title compound, showing the formation of the three-dimensional network by hydrogen bonds and π–π interactions. H atoms not involved in the motif have been omitted for clarity.

[N,N,N',N'-Tetrakis(benzimidazol-2-ylmethyl)cyclohexane- 1,2-trans-diamine]iron(II) bis(perchlorate) methanol solvate top

Crystal data top

[Fe(C₃₈H₃₈N₁₀)](ClO₄)₂·CH₄O	F(000) = 1912
M_r = 921.58	D_x = 1.459 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8487 reflections
a = 14.3867 (6) Å	θ = 2.4–28.0°
b = 15.9145 (6) Å	µ = 0.55 mm⁻¹
c = 18.8218 (8) Å	T = 298 K
β = 103.175 (1)°	Block, colorless
V = 4196.0 (3) Å³	0.30 × 0.16 × 0.10 mm
Z = 4

Data collection top

Bruker APEX CCD diffractometer	5765 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.083
Graphite monochromator	θ_max = 25.0°, θ_min = 2.0°
ϕ and ω scans	h = −15→17
21311 measured reflections	k = −17→18
7369 independent reflections	l = −22→22

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.176	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.1022P)² + 2.0578P] where P = (F_o² + 2F_c²)/3
7369 reflections	(Δ/σ)_max < 0.001
612 parameters	Δρ_max = 0.57 e Å⁻³
10 restraints	Δρ_min = −0.53 e Å⁻³

Crystal data top

[Fe(C₃₈H₃₈N₁₀)](ClO₄)₂·CH₄O	V = 4196.0 (3) Å³
M_r = 921.58	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 14.3867 (6) Å	µ = 0.55 mm⁻¹
b = 15.9145 (6) Å	T = 298 K
c = 18.8218 (8) Å	0.30 × 0.16 × 0.10 mm
β = 103.175 (1)°

Data collection top

Bruker APEX CCD diffractometer	5765 reflections with I > 2σ(I)
21311 measured reflections	R_int = 0.083
7369 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	10 restraints
wR(F²) = 0.176	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.57 e Å⁻³
7369 reflections	Δρ_min = −0.53 e Å⁻³
612 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Fe1	0.49217 (3)	0.51266 (3)	0.25944 (3)	0.03221 (18)
N1	0.40904 (18)	0.63557 (16)	0.22008 (16)	0.0340 (6)
N2	0.59753 (19)	0.61865 (17)	0.31077 (17)	0.0367 (7)
N3	0.5240 (2)	0.53017 (17)	0.15388 (17)	0.0387 (7)
N4	0.5194 (2)	0.61519 (17)	0.06081 (16)	0.0378 (7)
H4A	0.5027	0.6569	0.0317	0.045*
N5	0.35367 (19)	0.46902 (17)	0.21018 (16)	0.0357 (6)
N6	0.2082 (2)	0.50488 (18)	0.15204 (17)	0.0399 (7)
H6A	0.1577	0.5350	0.1380	0.048*
N7	0.62225 (19)	0.45068 (17)	0.29869 (16)	0.0370 (7)
N8	0.7795 (2)	0.4561 (2)	0.33400 (18)	0.0455 (8)
H8A	0.8364	0.4764	0.3434	0.055*
N9	0.4597 (2)	0.52468 (17)	0.36472 (17)	0.0389 (7)
N10	0.4732 (2)	0.60837 (17)	0.45995 (16)	0.0418 (7)
H10A	0.4973	0.6451	0.4925	0.050*
C1	0.4544 (2)	0.7063 (2)	0.2673 (2)	0.0377 (8)
H1A	0.4429	0.6957	0.3159	0.045*
C2	0.4124 (3)	0.7932 (2)	0.2440 (3)	0.0510 (10)
H2A	0.348 (3)	0.795 (3)	0.251 (3)	0.066 (13)*
H2B	0.407 (3)	0.800 (3)	0.196 (3)	0.061 (14)*
C3	0.4708 (3)	0.8639 (2)	0.2853 (3)	0.0591 (11)
H3A	0.4433	0.9174	0.2666	0.071*
H3B	0.4694	0.8605	0.3365	0.071*
C4	0.5723 (3)	0.8592 (2)	0.2776 (3)	0.0580 (11)
H4B	0.6082	0.9065	0.3024	0.070*
H4C	0.5739	0.8622	0.2264	0.070*
C5	0.6177 (3)	0.7774 (2)	0.3101 (3)	0.0535 (10)
H5A	0.6826	0.7746	0.3037	0.064*
H5B	0.6203	0.7770	0.3620	0.064*
C6	0.5629 (2)	0.7006 (2)	0.2751 (2)	0.0379 (8)
H6B	0.5729	0.6976	0.2254	0.045*
C7	0.4096 (3)	0.6477 (2)	0.1418 (2)	0.0396 (8)
H7A	0.350 (2)	0.6305 (19)	0.1137 (19)	0.040 (10)*
H7B	0.416 (2)	0.705 (2)	0.131 (2)	0.040 (10)*
C8	0.4854 (2)	0.5975 (2)	0.11997 (19)	0.0349 (7)
C9	0.5883 (2)	0.5004 (2)	0.1148 (2)	0.0389 (8)
C10	0.6475 (3)	0.4303 (2)	0.1245 (2)	0.0509 (10)
H10B	0.6492	0.3930	0.1628	0.061*
C11	0.7036 (3)	0.4184 (3)	0.0751 (2)	0.0577 (11)
H11A	0.7429	0.3714	0.0797	0.069*
C12	0.7031 (3)	0.4747 (3)	0.0187 (2)	0.0533 (10)
H12A	0.7443	0.4656	−0.0121	0.064*
C13	0.6443 (3)	0.5431 (2)	0.0068 (2)	0.0466 (9)
H13A	0.6437	0.5801	−0.0316	0.056*
C14	0.5858 (2)	0.5544 (2)	0.0551 (2)	0.0366 (8)
C15	0.3110 (2)	0.6161 (2)	0.2272 (2)	0.0386 (8)
H15A	0.2659	0.6559	0.1994	0.046*
H15B	0.3071	0.6187	0.2779	0.046*
C16	0.2893 (2)	0.5288 (2)	0.1979 (2)	0.0369 (8)
C17	0.3114 (2)	0.4004 (2)	0.1689 (2)	0.0385 (8)
C18	0.3487 (3)	0.3210 (2)	0.1593 (2)	0.0522 (10)
H18A	0.4093	0.3049	0.1848	0.063*
C19	0.2916 (3)	0.2680 (3)	0.1104 (3)	0.0653 (12)
H19A	0.3138	0.2146	0.1028	0.078*
C20	0.2023 (3)	0.2922 (3)	0.0723 (3)	0.0657 (13)
H20A	0.1666	0.2550	0.0388	0.079*
C21	0.1638 (3)	0.3692 (3)	0.0818 (2)	0.0561 (11)
H21A	0.1030	0.3845	0.0562	0.067*
C22	0.2201 (2)	0.4226 (2)	0.1312 (2)	0.0427 (9)
C23	0.6903 (2)	0.5920 (2)	0.2965 (2)	0.0427 (8)
H23A	0.7424	0.6207	0.3293	0.051*
H23B	0.6928	0.6053	0.2467	0.051*
C24	0.6979 (2)	0.4993 (2)	0.3088 (2)	0.0398 (8)
C25	0.6562 (3)	0.3702 (2)	0.3196 (2)	0.0391 (8)
C26	0.6065 (3)	0.2960 (2)	0.3245 (2)	0.0521 (10)
H26A	0.5403	0.2936	0.3102	0.063*
C27	0.6593 (3)	0.2266 (3)	0.3514 (3)	0.0649 (12)
H27A	0.6284	0.1760	0.3549	0.078*
C28	0.7582 (4)	0.2303 (3)	0.3735 (3)	0.0711 (14)
H28A	0.7916	0.1822	0.3923	0.085*
C29	0.8079 (3)	0.3027 (3)	0.3685 (3)	0.0607 (12)
H29A	0.8741	0.3045	0.3824	0.073*
C30	0.7551 (3)	0.3730 (2)	0.3420 (2)	0.0438 (9)
C31	0.6018 (2)	0.6166 (2)	0.3898 (2)	0.0409 (8)
H31A	0.6125	0.6730	0.4096	0.049*
H31B	0.6549	0.5817	0.4140	0.049*
C32	0.5113 (2)	0.5826 (2)	0.4044 (2)	0.0379 (8)
C33	0.3809 (3)	0.5110 (2)	0.3957 (2)	0.0398 (8)
C34	0.3042 (3)	0.4574 (3)	0.3759 (2)	0.0539 (10)
H34A	0.2993	0.4199	0.3374	0.065*
C35	0.2348 (3)	0.4618 (3)	0.4160 (3)	0.0653 (12)
H35A	0.1823	0.4261	0.4043	0.078*
C36	0.2417 (3)	0.5179 (3)	0.4731 (3)	0.0636 (12)
H36A	0.1923	0.5203	0.4975	0.076*
C37	0.3185 (3)	0.5701 (3)	0.4948 (2)	0.0542 (10)
H37A	0.3234	0.6067	0.5340	0.065*
C38	0.3891 (3)	0.5654 (2)	0.4551 (2)	0.0407 (8)
Cl1	0.55488 (10)	0.17228 (8)	0.01931 (8)	0.0758 (4)
O1	0.5176 (5)	0.2430 (3)	0.0429 (3)	0.141 (2)
O2	0.6396 (4)	0.1476 (4)	0.0605 (3)	0.153 (2)
O3	0.4884 (4)	0.1073 (3)	0.0204 (3)	0.155 (2)
O4	0.5571 (4)	0.1862 (3)	−0.0548 (3)	0.1265 (18)
Cl2	0.4081 (5)	0.1971 (4)	0.4315 (5)	0.064 (2)	0.461 (14)
O5	0.3219 (10)	0.1788 (13)	0.4499 (11)	0.124 (7)	0.461 (14)
O6	0.4447 (13)	0.1189 (8)	0.4236 (10)	0.113 (7)	0.461 (14)
O7	0.3795 (11)	0.2458 (9)	0.3656 (7)	0.164 (7)	0.461 (14)
O8	0.4841 (6)	0.2349 (7)	0.4747 (8)	0.107 (6)	0.461 (14)
Cl2'	0.4056 (7)	0.1978 (6)	0.4416 (6)	0.088 (3)	0.539 (14)
O5'	0.3123 (10)	0.2126 (13)	0.4188 (11)	0.132 (6)	0.539 (14)
O6'	0.4301 (11)	0.1350 (10)	0.3880 (10)	0.111 (6)	0.539 (14)
O7'	0.4525 (10)	0.2711 (7)	0.4260 (7)	0.119 (5)	0.539 (14)
O8'	0.4341 (9)	0.1893 (8)	0.5185 (5)	0.132 (5)	0.539 (14)
O1S	0.9648 (3)	0.5167 (3)	0.3479 (3)	0.0902 (12)
H1S	0.9747	0.5408	0.3956	0.135*
C1S	0.9867 (6)	0.5786 (5)	0.3004 (5)	0.137 (3)
H1SA	1.0452	0.5637	0.2872	0.205*
H1SB	0.9942	0.6323	0.3242	0.205*
H1SC	0.9367	0.5828	0.2570	0.205*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.0279 (3)	0.0359 (3)	0.0307 (3)	0.00317 (18)	0.0022 (2)	0.00087 (19)
N1	0.0307 (14)	0.0382 (14)	0.0321 (16)	0.0003 (11)	0.0053 (12)	−0.0031 (12)
N2	0.0301 (14)	0.0376 (14)	0.0403 (18)	0.0020 (11)	0.0034 (13)	0.0022 (13)
N3	0.0371 (15)	0.0428 (15)	0.0354 (18)	0.0078 (13)	0.0064 (13)	0.0030 (13)
N4	0.0402 (16)	0.0375 (15)	0.0351 (18)	−0.0002 (12)	0.0074 (14)	0.0041 (12)
N5	0.0322 (14)	0.0384 (14)	0.0338 (17)	0.0007 (12)	0.0023 (13)	−0.0014 (12)
N6	0.0278 (14)	0.0522 (17)	0.0384 (19)	0.0019 (12)	0.0045 (13)	0.0007 (14)
N7	0.0332 (15)	0.0420 (15)	0.0336 (17)	0.0058 (12)	0.0029 (13)	0.0011 (13)
N8	0.0302 (15)	0.0588 (18)	0.046 (2)	0.0082 (14)	0.0065 (14)	0.0031 (15)
N9	0.0390 (16)	0.0411 (15)	0.0359 (18)	−0.0031 (13)	0.0072 (14)	−0.0012 (13)
N10	0.0536 (18)	0.0399 (15)	0.0297 (18)	−0.0009 (14)	0.0050 (15)	−0.0032 (13)
C1	0.0372 (18)	0.0363 (17)	0.040 (2)	0.0013 (14)	0.0088 (16)	0.0012 (15)
C2	0.052 (2)	0.040 (2)	0.061 (3)	0.0091 (17)	0.013 (2)	0.0029 (19)
C3	0.068 (3)	0.0371 (19)	0.077 (3)	0.0017 (18)	0.025 (2)	−0.001 (2)
C4	0.064 (3)	0.040 (2)	0.074 (3)	−0.0087 (18)	0.024 (2)	−0.001 (2)
C5	0.050 (2)	0.043 (2)	0.066 (3)	−0.0102 (17)	0.009 (2)	−0.0019 (19)
C6	0.0385 (18)	0.0369 (17)	0.037 (2)	0.0002 (14)	0.0065 (16)	0.0009 (15)
C7	0.041 (2)	0.044 (2)	0.031 (2)	0.0080 (16)	0.0022 (17)	0.0026 (16)
C8	0.0329 (17)	0.0390 (17)	0.0307 (19)	0.0000 (14)	0.0029 (15)	−0.0016 (14)
C9	0.0328 (18)	0.0439 (18)	0.039 (2)	0.0017 (14)	0.0059 (16)	−0.0040 (16)
C10	0.054 (2)	0.059 (2)	0.038 (2)	0.0169 (19)	0.0064 (19)	0.0040 (18)
C11	0.053 (2)	0.072 (3)	0.047 (3)	0.023 (2)	0.009 (2)	−0.007 (2)
C12	0.044 (2)	0.076 (3)	0.042 (2)	0.004 (2)	0.0161 (19)	−0.013 (2)
C13	0.046 (2)	0.057 (2)	0.037 (2)	−0.0071 (18)	0.0110 (18)	−0.0047 (18)
C14	0.0327 (17)	0.0410 (18)	0.034 (2)	−0.0061 (14)	0.0032 (15)	−0.0052 (15)
C15	0.0314 (17)	0.0427 (18)	0.041 (2)	0.0066 (14)	0.0066 (16)	−0.0005 (15)
C16	0.0310 (17)	0.0441 (18)	0.035 (2)	−0.0021 (14)	0.0064 (16)	0.0010 (15)
C17	0.0389 (18)	0.0442 (18)	0.032 (2)	−0.0054 (15)	0.0076 (16)	−0.0009 (15)
C18	0.050 (2)	0.046 (2)	0.056 (3)	0.0009 (18)	0.004 (2)	−0.0037 (19)
C19	0.074 (3)	0.049 (2)	0.072 (3)	−0.006 (2)	0.012 (3)	−0.015 (2)
C20	0.061 (3)	0.065 (3)	0.067 (3)	−0.018 (2)	0.008 (2)	−0.023 (2)
C21	0.040 (2)	0.068 (3)	0.057 (3)	−0.0132 (19)	0.003 (2)	−0.009 (2)
C22	0.0330 (18)	0.049 (2)	0.045 (2)	−0.0049 (15)	0.0084 (17)	0.0006 (17)
C23	0.0318 (17)	0.050 (2)	0.045 (2)	−0.0024 (15)	0.0053 (16)	0.0020 (17)
C24	0.0324 (18)	0.050 (2)	0.036 (2)	0.0072 (15)	0.0068 (16)	0.0013 (16)
C25	0.0437 (19)	0.0438 (18)	0.030 (2)	0.0102 (15)	0.0083 (16)	0.0006 (15)
C26	0.052 (2)	0.051 (2)	0.050 (3)	0.0073 (18)	0.006 (2)	0.0052 (19)
C27	0.076 (3)	0.049 (2)	0.067 (3)	0.009 (2)	0.013 (3)	0.014 (2)
C28	0.072 (3)	0.061 (3)	0.080 (4)	0.031 (2)	0.017 (3)	0.023 (2)
C29	0.047 (2)	0.078 (3)	0.055 (3)	0.025 (2)	0.009 (2)	0.014 (2)
C30	0.042 (2)	0.056 (2)	0.034 (2)	0.0174 (17)	0.0107 (17)	0.0063 (17)
C31	0.0411 (19)	0.0462 (19)	0.031 (2)	−0.0019 (15)	−0.0010 (16)	−0.0008 (15)
C32	0.0377 (18)	0.0348 (17)	0.037 (2)	0.0020 (14)	0.0002 (16)	0.0012 (15)
C33	0.043 (2)	0.0390 (17)	0.038 (2)	0.0014 (15)	0.0102 (17)	0.0038 (15)
C34	0.058 (2)	0.062 (2)	0.043 (2)	−0.014 (2)	0.016 (2)	−0.003 (2)
C35	0.061 (3)	0.080 (3)	0.058 (3)	−0.020 (2)	0.020 (2)	0.002 (2)
C36	0.060 (3)	0.080 (3)	0.057 (3)	0.000 (2)	0.029 (2)	0.012 (2)
C37	0.073 (3)	0.058 (2)	0.036 (2)	0.009 (2)	0.021 (2)	0.0058 (18)
C38	0.051 (2)	0.0412 (18)	0.030 (2)	0.0043 (16)	0.0090 (17)	0.0067 (15)
Cl1	0.0785 (8)	0.0682 (7)	0.0822 (10)	0.0197 (6)	0.0213 (7)	0.0329 (6)
O1	0.202 (6)	0.101 (3)	0.129 (4)	0.045 (4)	0.054 (4)	0.023 (3)
O2	0.094 (3)	0.226 (6)	0.129 (5)	0.047 (4)	0.005 (3)	0.070 (4)
O3	0.178 (5)	0.140 (4)	0.133 (5)	−0.067 (4)	0.004 (4)	0.063 (4)
O4	0.127 (4)	0.156 (4)	0.107 (4)	0.032 (3)	0.049 (3)	0.068 (3)
Cl2	0.032 (3)	0.045 (3)	0.104 (6)	−0.0110 (19)	−0.007 (3)	−0.011 (3)
O5	0.092 (12)	0.167 (17)	0.130 (16)	−0.052 (10)	0.058 (11)	−0.013 (10)
O6	0.088 (8)	0.090 (8)	0.142 (18)	0.001 (6)	−0.012 (10)	−0.056 (10)
O7	0.157 (13)	0.176 (14)	0.145 (14)	−0.023 (11)	0.002 (11)	0.020 (11)
O8	0.077 (6)	0.082 (7)	0.130 (13)	−0.008 (5)	−0.044 (7)	−0.048 (8)
Cl2'	0.073 (4)	0.110 (5)	0.081 (3)	−0.029 (3)	0.021 (3)	−0.032 (3)
O5'	0.071 (7)	0.172 (16)	0.143 (16)	0.004 (8)	0.006 (8)	−0.025 (11)
O6'	0.083 (8)	0.127 (10)	0.128 (14)	−0.045 (7)	0.032 (8)	−0.065 (8)
O7'	0.148 (12)	0.114 (8)	0.105 (9)	−0.065 (8)	0.048 (9)	−0.040 (6)
O8'	0.141 (10)	0.160 (10)	0.084 (7)	0.031 (8)	0.005 (6)	0.006 (6)
O1S	0.074 (2)	0.099 (3)	0.098 (3)	−0.019 (2)	0.023 (2)	−0.040 (2)
C1S	0.177 (8)	0.099 (5)	0.146 (8)	−0.022 (5)	0.062 (7)	−0.028 (5)

Geometric parameters (Å, º) top

Fe1—N7	2.095 (3)	C13—C14	1.384 (5)
Fe1—N5	2.114 (3)	C13—H13A	0.9300
Fe1—N9	2.145 (3)	C15—C16	1.500 (5)
Fe1—N3	2.156 (3)	C15—H15A	0.9700
Fe1—N1	2.324 (3)	C15—H15B	0.9700
Fe1—N2	2.326 (3)	C17—C22	1.388 (5)
N1—C15	1.479 (4)	C17—C18	1.401 (5)
N1—C7	1.488 (4)	C18—C19	1.374 (6)
N1—C1	1.489 (4)	C18—H18A	0.9300
N2—C31	1.475 (5)	C19—C20	1.376 (6)
N2—C23	1.482 (4)	C19—H19A	0.9300
N2—C6	1.499 (4)	C20—C21	1.372 (6)
N3—C8	1.305 (4)	C20—H20A	0.9300
N3—C9	1.390 (4)	C21—C22	1.379 (5)
N4—C8	1.344 (4)	C21—H21A	0.9300
N4—C14	1.382 (4)	C23—C24	1.495 (5)
N4—H4A	0.8600	C23—H23A	0.9700
N5—C16	1.312 (4)	C23—H23B	0.9700
N5—C17	1.397 (4)	C25—C30	1.389 (5)
N6—C16	1.339 (4)	C25—C26	1.394 (5)
N6—C22	1.389 (4)	C26—C27	1.369 (6)
N6—H6A	0.8600	C26—H26A	0.9300
N7—C24	1.314 (5)	C27—C28	1.389 (7)
N7—C25	1.396 (4)	C27—H27A	0.9300
N8—C24	1.350 (4)	C28—C29	1.371 (6)
N8—C30	1.385 (5)	C28—H28A	0.9300
N8—H8A	0.8600	C29—C30	1.380 (5)
N9—C32	1.305 (4)	C29—H29A	0.9300
N9—C33	1.405 (4)	C31—C32	1.493 (5)
N10—C32	1.350 (5)	C31—H31A	0.9700
N10—C38	1.375 (5)	C31—H31B	0.9700
N10—H10A	0.8600	C33—C34	1.376 (5)
C1—C2	1.532 (5)	C33—C38	1.398 (5)
C1—C6	1.537 (5)	C34—C35	1.383 (6)
C1—H1A	0.9800	C34—H34A	0.9300
C2—C3	1.510 (6)	C35—C36	1.383 (7)
C2—H2A	0.97 (5)	C35—H35A	0.9300
C2—H2B	0.90 (5)	C36—C37	1.369 (6)
C3—C4	1.503 (6)	C36—H36A	0.9300
C3—H3A	0.9700	C37—C38	1.394 (5)
C3—H3B	0.9700	C37—H37A	0.9300
C4—C5	1.521 (6)	Cl1—O2	1.346 (5)
C4—H4B	0.9700	Cl1—O1	1.364 (5)
C4—H4C	0.9700	Cl1—O3	1.413 (5)
C5—C6	1.521 (5)	Cl1—O4	1.421 (5)
C5—H5A	0.9700	Cl2—O8	1.347 (8)
C5—H5B	0.9700	Cl2—O6	1.373 (9)
C6—H6B	0.9800	Cl2—O5	1.392 (9)
C7—C8	1.483 (5)	Cl2—O7	1.441 (9)
C7—H7A	0.94 (3)	Cl2'—O5'	1.333 (15)
C7—H7B	0.94 (4)	Cl2'—O7'	1.411 (12)
C9—C10	1.390 (5)	Cl2'—O8'	1.418 (14)
C9—C14	1.409 (5)	Cl2'—O6'	1.517 (15)
C10—C11	1.375 (6)	O1S—C1S	1.414 (8)
C10—H10B	0.9300	O1S—H1S	0.9556
C11—C12	1.389 (6)	C1S—H1SA	0.9600
C11—H11A	0.9300	C1S—H1SB	0.9600
C12—C13	1.365 (6)	C1S—H1SC	0.9600
C12—H12A	0.9300

N7—Fe1—N5	132.58 (11)	C14—C13—H13A	121.8
N7—Fe1—N9	94.65 (11)	N4—C14—C13	132.6 (3)
N5—Fe1—N9	93.02 (11)	N4—C14—C9	104.9 (3)
N7—Fe1—N3	91.46 (11)	C13—C14—C9	122.4 (3)
N5—Fe1—N3	90.87 (11)	N1—C15—C16	106.5 (3)
N9—Fe1—N3	167.46 (11)	N1—C15—H15A	110.4
N7—Fe1—N1	149.54 (10)	C16—C15—H15A	110.4
N5—Fe1—N1	76.80 (10)	N1—C15—H15B	110.4
N9—Fe1—N1	90.85 (10)	C16—C15—H15B	110.4
N3—Fe1—N1	78.43 (10)	H15A—C15—H15B	108.6
N7—Fe1—N2	75.51 (10)	N5—C16—N6	112.6 (3)
N5—Fe1—N2	151.68 (10)	N5—C16—C15	121.8 (3)
N9—Fe1—N2	79.05 (11)	N6—C16—C15	125.3 (3)
N3—Fe1—N2	91.94 (11)	C22—C17—N5	109.1 (3)
N1—Fe1—N2	76.19 (10)	C22—C17—C18	120.7 (3)
C15—N1—C7	109.7 (3)	N5—C17—C18	130.2 (3)
C15—N1—C1	113.7 (3)	C19—C18—C17	116.8 (4)
C7—N1—C1	113.1 (3)	C19—C18—H18A	121.6
C15—N1—Fe1	103.09 (19)	C17—C18—H18A	121.6
C7—N1—Fe1	107.84 (19)	C18—C19—C20	121.4 (4)
C1—N1—Fe1	108.79 (19)	C18—C19—H19A	119.3
C31—N2—C23	110.2 (3)	C20—C19—H19A	119.3
C31—N2—C6	113.8 (3)	C21—C20—C19	122.6 (4)
C23—N2—C6	112.9 (3)	C21—C20—H20A	118.7
C31—N2—Fe1	106.03 (19)	C19—C20—H20A	118.7
C23—N2—Fe1	104.2 (2)	C20—C21—C22	116.4 (4)
C6—N2—Fe1	109.06 (19)	C20—C21—H21A	121.8
C8—N3—C9	106.4 (3)	C22—C21—H21A	121.8
C8—N3—Fe1	113.6 (2)	C21—C22—C17	122.0 (4)
C9—N3—Fe1	138.6 (2)	C21—C22—N6	132.9 (4)
C8—N4—C14	107.9 (3)	C17—C22—N6	105.0 (3)
C8—N4—H4A	126.1	N2—C23—C24	107.0 (3)
C14—N4—H4A	126.1	N2—C23—H23A	110.3
C16—N5—C17	105.6 (3)	C24—C23—H23A	110.3
C16—N5—Fe1	113.3 (2)	N2—C23—H23B	110.3
C17—N5—Fe1	138.4 (2)	C24—C23—H23B	110.3
C16—N6—C22	107.7 (3)	H23A—C23—H23B	108.6
C16—N6—H6A	126.1	N7—C24—N8	112.2 (3)
C22—N6—H6A	126.1	N7—C24—C23	122.0 (3)
C24—N7—C25	105.9 (3)	N8—C24—C23	125.8 (3)
C24—N7—Fe1	114.7 (2)	C30—C25—C26	120.8 (3)
C25—N7—Fe1	139.3 (2)	C30—C25—N7	108.9 (3)
C24—N8—C30	107.6 (3)	C26—C25—N7	130.1 (3)
C24—N8—H8A	126.2	C27—C26—C25	117.2 (4)
C30—N8—H8A	126.2	C27—C26—H26A	121.4
C32—N9—C33	106.2 (3)	C25—C26—H26A	121.4
C32—N9—Fe1	112.1 (2)	C26—C27—C28	121.4 (4)
C33—N9—Fe1	137.3 (3)	C26—C27—H27A	119.3
C32—N10—C38	107.7 (3)	C28—C27—H27A	119.3
C32—N10—H10A	126.2	C29—C28—C27	121.9 (4)
C38—N10—H10A	126.2	C29—C28—H28A	119.1
N1—C1—C2	114.9 (3)	C27—C28—H28A	119.1
N1—C1—C6	108.1 (3)	C28—C29—C30	117.0 (4)
C2—C1—C6	113.9 (3)	C28—C29—H29A	121.5
N1—C1—H1A	106.5	C30—C29—H29A	121.5
C2—C1—H1A	106.5	C29—C30—N8	132.9 (4)
C6—C1—H1A	106.5	C29—C30—C25	121.7 (4)
C3—C2—C1	112.9 (4)	N8—C30—C25	105.4 (3)
C3—C2—H2A	110 (3)	N2—C31—C32	110.9 (3)
C1—C2—H2A	108 (3)	N2—C31—H31A	109.5
C3—C2—H2B	110 (3)	C32—C31—H31A	109.5
C1—C2—H2B	110 (3)	N2—C31—H31B	109.5
H2A—C2—H2B	105 (4)	C32—C31—H31B	109.5
C4—C3—C2	110.6 (3)	H31A—C31—H31B	108.0
C4—C3—H3A	109.5	N9—C32—N10	112.4 (3)
C2—C3—H3A	109.5	N9—C32—C31	123.8 (3)
C4—C3—H3B	109.5	N10—C32—C31	123.9 (3)
C2—C3—H3B	109.5	C34—C33—C38	121.1 (3)
H3A—C3—H3B	108.1	C34—C33—N9	131.1 (3)
C3—C4—C5	109.9 (3)	C38—C33—N9	107.8 (3)
C3—C4—H4B	109.7	C33—C34—C35	117.1 (4)
C5—C4—H4B	109.7	C33—C34—H34A	121.4
C3—C4—H4C	109.7	C35—C34—H34A	121.4
C5—C4—H4C	109.7	C36—C35—C34	121.5 (4)
H4B—C4—H4C	108.2	C36—C35—H35A	119.2
C6—C5—C4	112.4 (3)	C34—C35—H35A	119.2
C6—C5—H5A	109.1	C37—C36—C35	122.3 (4)
C4—C5—H5A	109.1	C37—C36—H36A	118.9
C6—C5—H5B	109.1	C35—C36—H36A	118.9
C4—C5—H5B	109.1	C36—C37—C38	116.4 (4)
H5A—C5—H5B	107.8	C36—C37—H37A	121.8
N2—C6—C5	114.8 (3)	C38—C37—H37A	121.8
N2—C6—C1	108.7 (3)	N10—C38—C37	132.5 (4)
C5—C6—C1	114.2 (3)	N10—C38—C33	105.9 (3)
N2—C6—H6B	106.2	C37—C38—C33	121.5 (4)
C5—C6—H6B	106.2	O2—Cl1—O1	115.1 (4)
C1—C6—H6B	106.2	O2—Cl1—O3	107.8 (4)
C8—C7—N1	112.0 (3)	O1—Cl1—O3	106.4 (4)
C8—C7—H7A	109 (2)	O2—Cl1—O4	113.0 (3)
N1—C7—H7A	108 (2)	O1—Cl1—O4	106.9 (3)
C8—C7—H7B	110 (2)	O3—Cl1—O4	107.2 (3)
N1—C7—H7B	111 (2)	O8—Cl2—O6	101.0 (9)
H7A—C7—H7B	107 (3)	O8—Cl2—O5	126.2 (13)
N3—C8—N4	112.5 (3)	O6—Cl2—O5	102.8 (11)
N3—C8—C7	124.4 (3)	O8—Cl2—O7	108.3 (8)
N4—C8—C7	123.1 (3)	O6—Cl2—O7	115.9 (11)
C10—C9—N3	131.8 (4)	O5—Cl2—O7	103.3 (8)
C10—C9—C14	119.8 (3)	O5'—Cl2'—O7'	106.4 (14)
N3—C9—C14	108.4 (3)	O5'—Cl2'—O8'	112.4 (12)
C11—C10—C9	117.3 (4)	O7'—Cl2'—O8'	104.5 (11)
C11—C10—H10B	121.3	O5'—Cl2'—O6'	105.8 (12)
C9—C10—H10B	121.3	O7'—Cl2'—O6'	102.2 (10)
C10—C11—C12	121.7 (4)	O8'—Cl2'—O6'	123.9 (11)
C10—C11—H11A	119.1	C1S—O1S—H1S	107.9
C12—C11—H11A	119.1	O1S—C1S—H1SA	109.1
C13—C12—C11	122.3 (4)	O1S—C1S—H1SB	110.0
C13—C12—H12A	118.8	H1SA—C1S—H1SB	109.2
C11—C12—H12A	118.8	O1S—C1S—H1SC	110.7
C12—C13—C14	116.3 (4)	H1SA—C1S—H1SC	109.2
C12—C13—H13A	121.8	H1SB—C1S—H1SC	108.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O1ⁱ	0.86	2.10	2.952 (6)	171
N6—H6A···O6′ⁱⁱ	0.86	2.02	2.852 (15)	162
N6—H6A···O6ⁱⁱ	0.86	2.13	2.955 (16)	162
N8—H8A···O1S	0.86	1.94	2.790 (5)	170
N10—H10A···O7′ⁱⁱⁱ	0.86	2.04	2.896 (10)	176
N10—H10A···O8ⁱⁱⁱ	0.86	2.01	2.787 (12)	150
O1S—H1S···O3^iv	0.96	1.88	2.813 (6)	166
C7—H7B···O4ⁱ	0.94 (4)	2.34 (4)	3.202 (6)	152 (3)
C23—H23A···O2^iv	0.97	2.40	3.318 (6)	158

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

Experimental details

Crystal data
Chemical formula	[Fe(C₃₈H₃₈N₁₀)](ClO₄)₂·CH₄O
M_r	921.58
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	14.3867 (6), 15.9145 (6), 18.8218 (8)
β (°)	103.175 (1)
V (Å³)	4196.0 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.55
Crystal size (mm)	0.30 × 0.16 × 0.10

Data collection
Diffractometer	Bruker APEX CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	21311, 7369, 5765
R_int	0.083
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.176, 1.07
No. of reflections	7369
No. of parameters	612
No. of restraints	10
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.57, −0.53

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O1ⁱ	0.86	2.10	2.952 (6)	171
N6—H6A···O6'ⁱⁱ	0.86	2.02	2.852 (15)	162
N6—H6A···O6ⁱⁱ	0.86	2.13	2.955 (16)	162
N8—H8A···O1S	0.86	1.94	2.790 (5)	170
N10—H10A···O7'ⁱⁱⁱ	0.86	2.04	2.896 (10)	176
N10—H10A···O8ⁱⁱⁱ	0.86	2.01	2.787 (12)	150
O1S—H1S···O3^iv	0.96	1.88	2.813 (6)	166
C7—H7B···O4ⁱ	0.94 (4)	2.34 (4)	3.202 (6)	152 (3)
C23—H23A···O2^iv	0.97	2.40	3.318 (6)	158

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

Acknowledgements

We thank the Youth Chen-Guang Project of Wuhan (grant No. 200850731361) for financially support of this study.

References

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Volume 67| Part 5| May 2011| Page m531

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

[N,N,N′,N′-Tetra­kis(benzimidazol-2-ylmeth­yl)cyclo­hexane-1,2-trans-di­amine]­iron(II) bis­­(perchlorate) methanol solvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

[N,N,N′,N′-Tetrakis(benzimidazol-2-ylmethyl)cyclohexane-1,2-trans-diamine]iron(II) bis(perchlorate) methanol solvate