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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

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

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 FeII 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 ππ 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[Main, F. (1992). Coord. Chem. Rev. 120, 325-359.]). For iron complexes with N,N,N′,N′-tetra­kis­(2-benzimidazolylmeth­yl)cyclo­hexane-1,2-trans-diamine, see: Mei et al. (2010[Mei, F.-S., Ou, C.-P., Wu, G.-L., Cao, L., Han, F., Meng, X.-G., Li, J., Li, D.-F. & Liao, Z.-R. (2010). Dalton Trans. pp. 4267-4269.]); Zhao et al. (2005[Zhao, X.-Z., Meng, X.-G. & Liao, Z.-R. (2005). Chem. J. Chin. Univ. 26, 1194-1197.]). For the synthesis of the ligand, see: Hendriks et al. (1982[Hendriks, M. J., Birker, J. M. W. L., van Rijn, J., Verschoor, G. C. & Reedijk, J. (1982). J. Am. Chem. Soc. 104, 3607-3617.]).

[Scheme 1]

Experimental

Crystal data
  • [Fe(C38H38N10)](ClO4)2·CH4O

  • Mr = 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)

  • Rint = 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

  • Δρmax = 0.57 e Å−3

  • Δρmin = −0.53 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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⋯O3iv 0.96 1.88 2.813 (6) 166
C7—H7B⋯O4i 0.94 (4) 2.34 (4) 3.202 (6) 152 (3)
C23—H23A⋯O2iv 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[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: PLATON.

Supporting information


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 FeII 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 FeII atom than the four bzim N atoms [average Fe—Namine = 2.325 (3), Fe—Nbzim = 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 ππ 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.

Refinement top

One of the perchlorate anions is disordered over two positions and the command 'DFIX' was used in the refinements. The final most satisfactory occupancies for the major and minor components were 0.539 (14) and 0.461 (14), respectively.

C-bound H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 (aromatic), 0.97 (methylene) and 0.96 (methyl) Å and Uiso(H) = 1.2(1.5 for methyl)Ueq(C). H atoms attached to C2 and C7 were refined isotropically. N- and O-bound H atoms were first found in difference Fourier maps and then placed at their ideal postions, with N—H = 0.86 and O—H = 0.82 Å and Uiso(H) = 1.2Ueq(N) or 1.5Ueq(O).

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
[Figure 1] Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity.
[Figure 2] Fig. 2. Crystal packing of the title compound, showing the formation of the three-dimensional network by hydrogen bonds and ππ 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·CH4OF(000) = 1912
Mr = 921.58Dx = 1.459 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 8487 reflections
a = 14.3867 (6) Åθ = 2.4–28.0°
b = 15.9145 (6) ŵ = 0.55 mm1
c = 18.8218 (8) ÅT = 298 K
β = 103.175 (1)°Block, colorless
V = 4196.0 (3) Å30.30 × 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 tubeRint = 0.083
Graphite monochromatorθmax = 25.0°, θmin = 2.0°
ϕ and ω scansh = 1517
21311 measured reflectionsk = 1718
7369 independent reflectionsl = 2222
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.176H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.1022P)2 + 2.0578P]
where P = (Fo2 + 2Fc2)/3
7369 reflections(Δ/σ)max < 0.001
612 parametersΔρmax = 0.57 e Å3
10 restraintsΔρmin = 0.53 e Å3
Crystal data top
[Fe(C38H38N10)](ClO4)2·CH4OV = 4196.0 (3) Å3
Mr = 921.58Z = 4
Monoclinic, P21/nMo Kα radiation
a = 14.3867 (6) ŵ = 0.55 mm1
b = 15.9145 (6) ÅT = 298 K
c = 18.8218 (8) Å0.30 × 0.16 × 0.10 mm
β = 103.175 (1)°
Data collection top
Bruker APEX CCD
diffractometer
5765 reflections with I > 2σ(I)
21311 measured reflectionsRint = 0.083
7369 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05610 restraints
wR(F2) = 0.176H atoms treated by a mixture of independent and constrained refinement
S = 1.07Δρmax = 0.57 e Å3
7369 reflectionsΔρmin = 0.53 e Å3
612 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Fe10.49217 (3)0.51266 (3)0.25944 (3)0.03221 (18)
N10.40904 (18)0.63557 (16)0.22008 (16)0.0340 (6)
N20.59753 (19)0.61865 (17)0.31077 (17)0.0367 (7)
N30.5240 (2)0.53017 (17)0.15388 (17)0.0387 (7)
N40.5194 (2)0.61519 (17)0.06081 (16)0.0378 (7)
H4A0.50270.65690.03170.045*
N50.35367 (19)0.46902 (17)0.21018 (16)0.0357 (6)
N60.2082 (2)0.50488 (18)0.15204 (17)0.0399 (7)
H6A0.15770.53500.13800.048*
N70.62225 (19)0.45068 (17)0.29869 (16)0.0370 (7)
N80.7795 (2)0.4561 (2)0.33400 (18)0.0455 (8)
H8A0.83640.47640.34340.055*
N90.4597 (2)0.52468 (17)0.36472 (17)0.0389 (7)
N100.4732 (2)0.60837 (17)0.45995 (16)0.0418 (7)
H10A0.49730.64510.49250.050*
C10.4544 (2)0.7063 (2)0.2673 (2)0.0377 (8)
H1A0.44290.69570.31590.045*
C20.4124 (3)0.7932 (2)0.2440 (3)0.0510 (10)
H2A0.348 (3)0.795 (3)0.251 (3)0.066 (13)*
H2B0.407 (3)0.800 (3)0.196 (3)0.061 (14)*
C30.4708 (3)0.8639 (2)0.2853 (3)0.0591 (11)
H3A0.44330.91740.26660.071*
H3B0.46940.86050.33650.071*
C40.5723 (3)0.8592 (2)0.2776 (3)0.0580 (11)
H4B0.60820.90650.30240.070*
H4C0.57390.86220.22640.070*
C50.6177 (3)0.7774 (2)0.3101 (3)0.0535 (10)
H5A0.68260.77460.30370.064*
H5B0.62030.77700.36200.064*
C60.5629 (2)0.7006 (2)0.2751 (2)0.0379 (8)
H6B0.57290.69760.22540.045*
C70.4096 (3)0.6477 (2)0.1418 (2)0.0396 (8)
H7A0.350 (2)0.6305 (19)0.1137 (19)0.040 (10)*
H7B0.416 (2)0.705 (2)0.131 (2)0.040 (10)*
C80.4854 (2)0.5975 (2)0.11997 (19)0.0349 (7)
C90.5883 (2)0.5004 (2)0.1148 (2)0.0389 (8)
C100.6475 (3)0.4303 (2)0.1245 (2)0.0509 (10)
H10B0.64920.39300.16280.061*
C110.7036 (3)0.4184 (3)0.0751 (2)0.0577 (11)
H11A0.74290.37140.07970.069*
C120.7031 (3)0.4747 (3)0.0187 (2)0.0533 (10)
H12A0.74430.46560.01210.064*
C130.6443 (3)0.5431 (2)0.0068 (2)0.0466 (9)
H13A0.64370.58010.03160.056*
C140.5858 (2)0.5544 (2)0.0551 (2)0.0366 (8)
C150.3110 (2)0.6161 (2)0.2272 (2)0.0386 (8)
H15A0.26590.65590.19940.046*
H15B0.30710.61870.27790.046*
C160.2893 (2)0.5288 (2)0.1979 (2)0.0369 (8)
C170.3114 (2)0.4004 (2)0.1689 (2)0.0385 (8)
C180.3487 (3)0.3210 (2)0.1593 (2)0.0522 (10)
H18A0.40930.30490.18480.063*
C190.2916 (3)0.2680 (3)0.1104 (3)0.0653 (12)
H19A0.31380.21460.10280.078*
C200.2023 (3)0.2922 (3)0.0723 (3)0.0657 (13)
H20A0.16660.25500.03880.079*
C210.1638 (3)0.3692 (3)0.0818 (2)0.0561 (11)
H21A0.10300.38450.05620.067*
C220.2201 (2)0.4226 (2)0.1312 (2)0.0427 (9)
C230.6903 (2)0.5920 (2)0.2965 (2)0.0427 (8)
H23A0.74240.62070.32930.051*
H23B0.69280.60530.24670.051*
C240.6979 (2)0.4993 (2)0.3088 (2)0.0398 (8)
C250.6562 (3)0.3702 (2)0.3196 (2)0.0391 (8)
C260.6065 (3)0.2960 (2)0.3245 (2)0.0521 (10)
H26A0.54030.29360.31020.063*
C270.6593 (3)0.2266 (3)0.3514 (3)0.0649 (12)
H27A0.62840.17600.35490.078*
C280.7582 (4)0.2303 (3)0.3735 (3)0.0711 (14)
H28A0.79160.18220.39230.085*
C290.8079 (3)0.3027 (3)0.3685 (3)0.0607 (12)
H29A0.87410.30450.38240.073*
C300.7551 (3)0.3730 (2)0.3420 (2)0.0438 (9)
C310.6018 (2)0.6166 (2)0.3898 (2)0.0409 (8)
H31A0.61250.67300.40960.049*
H31B0.65490.58170.41400.049*
C320.5113 (2)0.5826 (2)0.4044 (2)0.0379 (8)
C330.3809 (3)0.5110 (2)0.3957 (2)0.0398 (8)
C340.3042 (3)0.4574 (3)0.3759 (2)0.0539 (10)
H34A0.29930.41990.33740.065*
C350.2348 (3)0.4618 (3)0.4160 (3)0.0653 (12)
H35A0.18230.42610.40430.078*
C360.2417 (3)0.5179 (3)0.4731 (3)0.0636 (12)
H36A0.19230.52030.49750.076*
C370.3185 (3)0.5701 (3)0.4948 (2)0.0542 (10)
H37A0.32340.60670.53400.065*
C380.3891 (3)0.5654 (2)0.4551 (2)0.0407 (8)
Cl10.55488 (10)0.17228 (8)0.01931 (8)0.0758 (4)
O10.5176 (5)0.2430 (3)0.0429 (3)0.141 (2)
O20.6396 (4)0.1476 (4)0.0605 (3)0.153 (2)
O30.4884 (4)0.1073 (3)0.0204 (3)0.155 (2)
O40.5571 (4)0.1862 (3)0.0548 (3)0.1265 (18)
Cl20.4081 (5)0.1971 (4)0.4315 (5)0.064 (2)0.461 (14)
O50.3219 (10)0.1788 (13)0.4499 (11)0.124 (7)0.461 (14)
O60.4447 (13)0.1189 (8)0.4236 (10)0.113 (7)0.461 (14)
O70.3795 (11)0.2458 (9)0.3656 (7)0.164 (7)0.461 (14)
O80.4841 (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)
O1S0.9648 (3)0.5167 (3)0.3479 (3)0.0902 (12)
H1S0.97470.54080.39560.135*
C1S0.9867 (6)0.5786 (5)0.3004 (5)0.137 (3)
H1SA1.04520.56370.28720.205*
H1SB0.99420.63230.32420.205*
H1SC0.93670.58280.25700.205*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0279 (3)0.0359 (3)0.0307 (3)0.00317 (18)0.0022 (2)0.00087 (19)
N10.0307 (14)0.0382 (14)0.0321 (16)0.0003 (11)0.0053 (12)0.0031 (12)
N20.0301 (14)0.0376 (14)0.0403 (18)0.0020 (11)0.0034 (13)0.0022 (13)
N30.0371 (15)0.0428 (15)0.0354 (18)0.0078 (13)0.0064 (13)0.0030 (13)
N40.0402 (16)0.0375 (15)0.0351 (18)0.0002 (12)0.0074 (14)0.0041 (12)
N50.0322 (14)0.0384 (14)0.0338 (17)0.0007 (12)0.0023 (13)0.0014 (12)
N60.0278 (14)0.0522 (17)0.0384 (19)0.0019 (12)0.0045 (13)0.0007 (14)
N70.0332 (15)0.0420 (15)0.0336 (17)0.0058 (12)0.0029 (13)0.0011 (13)
N80.0302 (15)0.0588 (18)0.046 (2)0.0082 (14)0.0065 (14)0.0031 (15)
N90.0390 (16)0.0411 (15)0.0359 (18)0.0031 (13)0.0072 (14)0.0012 (13)
N100.0536 (18)0.0399 (15)0.0297 (18)0.0009 (14)0.0050 (15)0.0032 (13)
C10.0372 (18)0.0363 (17)0.040 (2)0.0013 (14)0.0088 (16)0.0012 (15)
C20.052 (2)0.040 (2)0.061 (3)0.0091 (17)0.013 (2)0.0029 (19)
C30.068 (3)0.0371 (19)0.077 (3)0.0017 (18)0.025 (2)0.001 (2)
C40.064 (3)0.040 (2)0.074 (3)0.0087 (18)0.024 (2)0.001 (2)
C50.050 (2)0.043 (2)0.066 (3)0.0102 (17)0.009 (2)0.0019 (19)
C60.0385 (18)0.0369 (17)0.037 (2)0.0002 (14)0.0065 (16)0.0009 (15)
C70.041 (2)0.044 (2)0.031 (2)0.0080 (16)0.0022 (17)0.0026 (16)
C80.0329 (17)0.0390 (17)0.0307 (19)0.0000 (14)0.0029 (15)0.0016 (14)
C90.0328 (18)0.0439 (18)0.039 (2)0.0017 (14)0.0059 (16)0.0040 (16)
C100.054 (2)0.059 (2)0.038 (2)0.0169 (19)0.0064 (19)0.0040 (18)
C110.053 (2)0.072 (3)0.047 (3)0.023 (2)0.009 (2)0.007 (2)
C120.044 (2)0.076 (3)0.042 (2)0.004 (2)0.0161 (19)0.013 (2)
C130.046 (2)0.057 (2)0.037 (2)0.0071 (18)0.0110 (18)0.0047 (18)
C140.0327 (17)0.0410 (18)0.034 (2)0.0061 (14)0.0032 (15)0.0052 (15)
C150.0314 (17)0.0427 (18)0.041 (2)0.0066 (14)0.0066 (16)0.0005 (15)
C160.0310 (17)0.0441 (18)0.035 (2)0.0021 (14)0.0064 (16)0.0010 (15)
C170.0389 (18)0.0442 (18)0.032 (2)0.0054 (15)0.0076 (16)0.0009 (15)
C180.050 (2)0.046 (2)0.056 (3)0.0009 (18)0.004 (2)0.0037 (19)
C190.074 (3)0.049 (2)0.072 (3)0.006 (2)0.012 (3)0.015 (2)
C200.061 (3)0.065 (3)0.067 (3)0.018 (2)0.008 (2)0.023 (2)
C210.040 (2)0.068 (3)0.057 (3)0.0132 (19)0.003 (2)0.009 (2)
C220.0330 (18)0.049 (2)0.045 (2)0.0049 (15)0.0084 (17)0.0006 (17)
C230.0318 (17)0.050 (2)0.045 (2)0.0024 (15)0.0053 (16)0.0020 (17)
C240.0324 (18)0.050 (2)0.036 (2)0.0072 (15)0.0068 (16)0.0013 (16)
C250.0437 (19)0.0438 (18)0.030 (2)0.0102 (15)0.0083 (16)0.0006 (15)
C260.052 (2)0.051 (2)0.050 (3)0.0073 (18)0.006 (2)0.0052 (19)
C270.076 (3)0.049 (2)0.067 (3)0.009 (2)0.013 (3)0.014 (2)
C280.072 (3)0.061 (3)0.080 (4)0.031 (2)0.017 (3)0.023 (2)
C290.047 (2)0.078 (3)0.055 (3)0.025 (2)0.009 (2)0.014 (2)
C300.042 (2)0.056 (2)0.034 (2)0.0174 (17)0.0107 (17)0.0063 (17)
C310.0411 (19)0.0462 (19)0.031 (2)0.0019 (15)0.0010 (16)0.0008 (15)
C320.0377 (18)0.0348 (17)0.037 (2)0.0020 (14)0.0002 (16)0.0012 (15)
C330.043 (2)0.0390 (17)0.038 (2)0.0014 (15)0.0102 (17)0.0038 (15)
C340.058 (2)0.062 (2)0.043 (2)0.014 (2)0.016 (2)0.003 (2)
C350.061 (3)0.080 (3)0.058 (3)0.020 (2)0.020 (2)0.002 (2)
C360.060 (3)0.080 (3)0.057 (3)0.000 (2)0.029 (2)0.012 (2)
C370.073 (3)0.058 (2)0.036 (2)0.009 (2)0.021 (2)0.0058 (18)
C380.051 (2)0.0412 (18)0.030 (2)0.0043 (16)0.0090 (17)0.0067 (15)
Cl10.0785 (8)0.0682 (7)0.0822 (10)0.0197 (6)0.0213 (7)0.0329 (6)
O10.202 (6)0.101 (3)0.129 (4)0.045 (4)0.054 (4)0.023 (3)
O20.094 (3)0.226 (6)0.129 (5)0.047 (4)0.005 (3)0.070 (4)
O30.178 (5)0.140 (4)0.133 (5)0.067 (4)0.004 (4)0.063 (4)
O40.127 (4)0.156 (4)0.107 (4)0.032 (3)0.049 (3)0.068 (3)
Cl20.032 (3)0.045 (3)0.104 (6)0.0110 (19)0.007 (3)0.011 (3)
O50.092 (12)0.167 (17)0.130 (16)0.052 (10)0.058 (11)0.013 (10)
O60.088 (8)0.090 (8)0.142 (18)0.001 (6)0.012 (10)0.056 (10)
O70.157 (13)0.176 (14)0.145 (14)0.023 (11)0.002 (11)0.020 (11)
O80.077 (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)
O1S0.074 (2)0.099 (3)0.098 (3)0.019 (2)0.023 (2)0.040 (2)
C1S0.177 (8)0.099 (5)0.146 (8)0.022 (5)0.062 (7)0.028 (5)
Geometric parameters (Å, º) top
Fe1—N72.095 (3)C13—C141.384 (5)
Fe1—N52.114 (3)C13—H13A0.9300
Fe1—N92.145 (3)C15—C161.500 (5)
Fe1—N32.156 (3)C15—H15A0.9700
Fe1—N12.324 (3)C15—H15B0.9700
Fe1—N22.326 (3)C17—C221.388 (5)
N1—C151.479 (4)C17—C181.401 (5)
N1—C71.488 (4)C18—C191.374 (6)
N1—C11.489 (4)C18—H18A0.9300
N2—C311.475 (5)C19—C201.376 (6)
N2—C231.482 (4)C19—H19A0.9300
N2—C61.499 (4)C20—C211.372 (6)
N3—C81.305 (4)C20—H20A0.9300
N3—C91.390 (4)C21—C221.379 (5)
N4—C81.344 (4)C21—H21A0.9300
N4—C141.382 (4)C23—C241.495 (5)
N4—H4A0.8600C23—H23A0.9700
N5—C161.312 (4)C23—H23B0.9700
N5—C171.397 (4)C25—C301.389 (5)
N6—C161.339 (4)C25—C261.394 (5)
N6—C221.389 (4)C26—C271.369 (6)
N6—H6A0.8600C26—H26A0.9300
N7—C241.314 (5)C27—C281.389 (7)
N7—C251.396 (4)C27—H27A0.9300
N8—C241.350 (4)C28—C291.371 (6)
N8—C301.385 (5)C28—H28A0.9300
N8—H8A0.8600C29—C301.380 (5)
N9—C321.305 (4)C29—H29A0.9300
N9—C331.405 (4)C31—C321.493 (5)
N10—C321.350 (5)C31—H31A0.9700
N10—C381.375 (5)C31—H31B0.9700
N10—H10A0.8600C33—C341.376 (5)
C1—C21.532 (5)C33—C381.398 (5)
C1—C61.537 (5)C34—C351.383 (6)
C1—H1A0.9800C34—H34A0.9300
C2—C31.510 (6)C35—C361.383 (7)
C2—H2A0.97 (5)C35—H35A0.9300
C2—H2B0.90 (5)C36—C371.369 (6)
C3—C41.503 (6)C36—H36A0.9300
C3—H3A0.9700C37—C381.394 (5)
C3—H3B0.9700C37—H37A0.9300
C4—C51.521 (6)Cl1—O21.346 (5)
C4—H4B0.9700Cl1—O11.364 (5)
C4—H4C0.9700Cl1—O31.413 (5)
C5—C61.521 (5)Cl1—O41.421 (5)
C5—H5A0.9700Cl2—O81.347 (8)
C5—H5B0.9700Cl2—O61.373 (9)
C6—H6B0.9800Cl2—O51.392 (9)
C7—C81.483 (5)Cl2—O71.441 (9)
C7—H7A0.94 (3)Cl2'—O5'1.333 (15)
C7—H7B0.94 (4)Cl2'—O7'1.411 (12)
C9—C101.390 (5)Cl2'—O8'1.418 (14)
C9—C141.409 (5)Cl2'—O6'1.517 (15)
C10—C111.375 (6)O1S—C1S1.414 (8)
C10—H10B0.9300O1S—H1S0.9556
C11—C121.389 (6)C1S—H1SA0.9600
C11—H11A0.9300C1S—H1SB0.9600
C12—C131.365 (6)C1S—H1SC0.9600
C12—H12A0.9300
N7—Fe1—N5132.58 (11)C14—C13—H13A121.8
N7—Fe1—N994.65 (11)N4—C14—C13132.6 (3)
N5—Fe1—N993.02 (11)N4—C14—C9104.9 (3)
N7—Fe1—N391.46 (11)C13—C14—C9122.4 (3)
N5—Fe1—N390.87 (11)N1—C15—C16106.5 (3)
N9—Fe1—N3167.46 (11)N1—C15—H15A110.4
N7—Fe1—N1149.54 (10)C16—C15—H15A110.4
N5—Fe1—N176.80 (10)N1—C15—H15B110.4
N9—Fe1—N190.85 (10)C16—C15—H15B110.4
N3—Fe1—N178.43 (10)H15A—C15—H15B108.6
N7—Fe1—N275.51 (10)N5—C16—N6112.6 (3)
N5—Fe1—N2151.68 (10)N5—C16—C15121.8 (3)
N9—Fe1—N279.05 (11)N6—C16—C15125.3 (3)
N3—Fe1—N291.94 (11)C22—C17—N5109.1 (3)
N1—Fe1—N276.19 (10)C22—C17—C18120.7 (3)
C15—N1—C7109.7 (3)N5—C17—C18130.2 (3)
C15—N1—C1113.7 (3)C19—C18—C17116.8 (4)
C7—N1—C1113.1 (3)C19—C18—H18A121.6
C15—N1—Fe1103.09 (19)C17—C18—H18A121.6
C7—N1—Fe1107.84 (19)C18—C19—C20121.4 (4)
C1—N1—Fe1108.79 (19)C18—C19—H19A119.3
C31—N2—C23110.2 (3)C20—C19—H19A119.3
C31—N2—C6113.8 (3)C21—C20—C19122.6 (4)
C23—N2—C6112.9 (3)C21—C20—H20A118.7
C31—N2—Fe1106.03 (19)C19—C20—H20A118.7
C23—N2—Fe1104.2 (2)C20—C21—C22116.4 (4)
C6—N2—Fe1109.06 (19)C20—C21—H21A121.8
C8—N3—C9106.4 (3)C22—C21—H21A121.8
C8—N3—Fe1113.6 (2)C21—C22—C17122.0 (4)
C9—N3—Fe1138.6 (2)C21—C22—N6132.9 (4)
C8—N4—C14107.9 (3)C17—C22—N6105.0 (3)
C8—N4—H4A126.1N2—C23—C24107.0 (3)
C14—N4—H4A126.1N2—C23—H23A110.3
C16—N5—C17105.6 (3)C24—C23—H23A110.3
C16—N5—Fe1113.3 (2)N2—C23—H23B110.3
C17—N5—Fe1138.4 (2)C24—C23—H23B110.3
C16—N6—C22107.7 (3)H23A—C23—H23B108.6
C16—N6—H6A126.1N7—C24—N8112.2 (3)
C22—N6—H6A126.1N7—C24—C23122.0 (3)
C24—N7—C25105.9 (3)N8—C24—C23125.8 (3)
C24—N7—Fe1114.7 (2)C30—C25—C26120.8 (3)
C25—N7—Fe1139.3 (2)C30—C25—N7108.9 (3)
C24—N8—C30107.6 (3)C26—C25—N7130.1 (3)
C24—N8—H8A126.2C27—C26—C25117.2 (4)
C30—N8—H8A126.2C27—C26—H26A121.4
C32—N9—C33106.2 (3)C25—C26—H26A121.4
C32—N9—Fe1112.1 (2)C26—C27—C28121.4 (4)
C33—N9—Fe1137.3 (3)C26—C27—H27A119.3
C32—N10—C38107.7 (3)C28—C27—H27A119.3
C32—N10—H10A126.2C29—C28—C27121.9 (4)
C38—N10—H10A126.2C29—C28—H28A119.1
N1—C1—C2114.9 (3)C27—C28—H28A119.1
N1—C1—C6108.1 (3)C28—C29—C30117.0 (4)
C2—C1—C6113.9 (3)C28—C29—H29A121.5
N1—C1—H1A106.5C30—C29—H29A121.5
C2—C1—H1A106.5C29—C30—N8132.9 (4)
C6—C1—H1A106.5C29—C30—C25121.7 (4)
C3—C2—C1112.9 (4)N8—C30—C25105.4 (3)
C3—C2—H2A110 (3)N2—C31—C32110.9 (3)
C1—C2—H2A108 (3)N2—C31—H31A109.5
C3—C2—H2B110 (3)C32—C31—H31A109.5
C1—C2—H2B110 (3)N2—C31—H31B109.5
H2A—C2—H2B105 (4)C32—C31—H31B109.5
C4—C3—C2110.6 (3)H31A—C31—H31B108.0
C4—C3—H3A109.5N9—C32—N10112.4 (3)
C2—C3—H3A109.5N9—C32—C31123.8 (3)
C4—C3—H3B109.5N10—C32—C31123.9 (3)
C2—C3—H3B109.5C34—C33—C38121.1 (3)
H3A—C3—H3B108.1C34—C33—N9131.1 (3)
C3—C4—C5109.9 (3)C38—C33—N9107.8 (3)
C3—C4—H4B109.7C33—C34—C35117.1 (4)
C5—C4—H4B109.7C33—C34—H34A121.4
C3—C4—H4C109.7C35—C34—H34A121.4
C5—C4—H4C109.7C36—C35—C34121.5 (4)
H4B—C4—H4C108.2C36—C35—H35A119.2
C6—C5—C4112.4 (3)C34—C35—H35A119.2
C6—C5—H5A109.1C37—C36—C35122.3 (4)
C4—C5—H5A109.1C37—C36—H36A118.9
C6—C5—H5B109.1C35—C36—H36A118.9
C4—C5—H5B109.1C36—C37—C38116.4 (4)
H5A—C5—H5B107.8C36—C37—H37A121.8
N2—C6—C5114.8 (3)C38—C37—H37A121.8
N2—C6—C1108.7 (3)N10—C38—C37132.5 (4)
C5—C6—C1114.2 (3)N10—C38—C33105.9 (3)
N2—C6—H6B106.2C37—C38—C33121.5 (4)
C5—C6—H6B106.2O2—Cl1—O1115.1 (4)
C1—C6—H6B106.2O2—Cl1—O3107.8 (4)
C8—C7—N1112.0 (3)O1—Cl1—O3106.4 (4)
C8—C7—H7A109 (2)O2—Cl1—O4113.0 (3)
N1—C7—H7A108 (2)O1—Cl1—O4106.9 (3)
C8—C7—H7B110 (2)O3—Cl1—O4107.2 (3)
N1—C7—H7B111 (2)O8—Cl2—O6101.0 (9)
H7A—C7—H7B107 (3)O8—Cl2—O5126.2 (13)
N3—C8—N4112.5 (3)O6—Cl2—O5102.8 (11)
N3—C8—C7124.4 (3)O8—Cl2—O7108.3 (8)
N4—C8—C7123.1 (3)O6—Cl2—O7115.9 (11)
C10—C9—N3131.8 (4)O5—Cl2—O7103.3 (8)
C10—C9—C14119.8 (3)O5'—Cl2'—O7'106.4 (14)
N3—C9—C14108.4 (3)O5'—Cl2'—O8'112.4 (12)
C11—C10—C9117.3 (4)O7'—Cl2'—O8'104.5 (11)
C11—C10—H10B121.3O5'—Cl2'—O6'105.8 (12)
C9—C10—H10B121.3O7'—Cl2'—O6'102.2 (10)
C10—C11—C12121.7 (4)O8'—Cl2'—O6'123.9 (11)
C10—C11—H11A119.1C1S—O1S—H1S107.9
C12—C11—H11A119.1O1S—C1S—H1SA109.1
C13—C12—C11122.3 (4)O1S—C1S—H1SB110.0
C13—C12—H12A118.8H1SA—C1S—H1SB109.2
C11—C12—H12A118.8O1S—C1S—H1SC110.7
C12—C13—C14116.3 (4)H1SA—C1S—H1SC109.2
C12—C13—H13A121.8H1SB—C1S—H1SC108.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4A···O1i0.862.102.952 (6)171
N6—H6A···O6ii0.862.022.852 (15)162
N6—H6A···O6ii0.862.132.955 (16)162
N8—H8A···O1S0.861.942.790 (5)170
N10—H10A···O7iii0.862.042.896 (10)176
N10—H10A···O8iii0.862.012.787 (12)150
O1S—H1S···O3iv0.961.882.813 (6)166
C7—H7B···O4i0.94 (4)2.34 (4)3.202 (6)152 (3)
C23—H23A···O2iv0.972.403.318 (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
Mr921.58
Crystal system, space groupMonoclinic, P21/n
Temperature (K)298
a, b, c (Å)14.3867 (6), 15.9145 (6), 18.8218 (8)
β (°) 103.175 (1)
V3)4196.0 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.55
Crystal size (mm)0.30 × 0.16 × 0.10
Data collection
DiffractometerBruker APEX CCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
21311, 7369, 5765
Rint0.083
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.176, 1.07
No. of reflections7369
No. of parameters612
No. of restraints10
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
N4—H4A···O1i0.862.102.952 (6)171
N6—H6A···O6'ii0.862.022.852 (15)162
N6—H6A···O6ii0.862.132.955 (16)162
N8—H8A···O1S0.861.942.790 (5)170
N10—H10A···O7'iii0.862.042.896 (10)176
N10—H10A···O8iii0.862.012.787 (12)150
O1S—H1S···O3iv0.961.882.813 (6)166
C7—H7B···O4i0.94 (4)2.34 (4)3.202 (6)152 (3)
C23—H23A···O2iv0.972.403.318 (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

First citationBruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationHendriks, M. J., Birker, J. M. W. L., van Rijn, J., Verschoor, G. C. & Reedijk, J. (1982). J. Am. Chem. Soc. 104, 3607–3617.  CSD CrossRef CAS Web of Science Google Scholar
First citationMain, F. (1992). Coord. Chem. Rev. 120, 325–359.  CrossRef Web of Science Google Scholar
First citationMei, F.-S., Ou, C.-P., Wu, G.-L., Cao, L., Han, F., Meng, X.-G., Li, J., Li, D.-F. & Liao, Z.-R. (2010). Dalton Trans. pp. 4267–4269.  CrossRef Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationZhao, X.-Z., Meng, X.-G. & Liao, Z.-R. (2005). Chem. J. Chin. Univ. 26, 1194–1197.  CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds