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Acta Cryst. (2009). E65, m788    [ doi:10.1107/S1600536809022442 ]

2,2'-Bis(ferrocenylmethyl)-5,5'-(m-phenylene)di-2H-tetrazole

F. Chen

Abstract top

In the title compound, [Fe2(C5H5)2(C20H16N8)], one of the unsubstituted cyclopentadiene (Cp) rings is disordered over two positions, with site-occupancy factors of 0.609 (19) and 0.391 (19). The dihedral angle formed by the benzene ring with the tetrazole rings are 51.86 (15) and 3.76 (11)°. In the crystal structure, centrosymmetrically related molecules are linked into dimers by intermolecular C-H...N hydrogen-bonding interactions.

Comment top

The chemistry of ferrocene has received much attention because of its applications in many fields, such as catalysis (Yang et al., 2002), organic or organometallic synthesis and materials (Togni & Hayashi, 1995), and non-linear optical (NLO) materials (Long, 1995; Roberto et al., 2000). As part of our continuing studies on new ferrocene compounds, the crystal structure of the title compound is reported herein.

In the title compound (Fig. 1), one of the unsubstituted cyclopentadiene (Cp) rings is disordered over two positions, with site-occupancy factors of 0.609 (19) and 0.391 (19) for the major and minor components, respectively. The dihedral angles formed within the (Cp)2Fe unit by the disordered components with the substituted Cp ring are 1.1 (4) and 1.7 (6)°. The benzene ring forms dihedral angles of 3.76 (11) and 51.86 (15)° with the N1–N4/C7 and N5–N8/C19 tetrazole rings, respectively. The Fe—C distances range from 2.00 (2) to 2.06 (3) Å, and are in agreement with those reported for related compounds (Hess et al., 1999; Base et al., 2002). In the crystal structure, centrosymmetrically related molecules are linked into dimers by intermolecular C—H···N hydrogen bonding interactions (Table 1).

Related literature top

For the applications of ferrocene derivatives, see: Yang et al. (2002); Togni & Hayashi (1995); Long (1995); Roberto et al. (2000). For the crystal structures of related compounds, see: Hess et al. (1999); Base et al. (2002); Cao & Ye (2008).

Experimental top

To a mixture of [Fe(C5H5)(C5H4)N+(CH3)3I-] (10 mmol) in H2O (50 ml) was added 5-(3-(2H-tetrazol-5-yl)phenyl)-2H-tetrazole (5 mmol) and the mixture was heated to reflux temperature for 5 h. Then, the formed yellow precipitate was filtered. Crystals suitable for X-ray diffraction analysis were obtained by slow evaporation of a dichloromethane solution at room temperature after 3 days.

Refinement top

Positional parameters of all the H atoms were calculated geometrically and were allowed to ride on their parent atoms, with C—H = 0.93-0.98 Å and with Uiso(H) = 1.2Uiso(C). One cyclopentadiene rings is disordered over two positions, with refined site-occupancy factors of 0.609 (19) and 0.391 (19) for the major and minor components, respectively. Soft proximity (SIMU) and rigid-bond restraints (DELU) were applied to the anisotropic displacement parameters.

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: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.
2,2'-Bis(ferrocenylmethyl)-5,5'-(m-phenylene)di-2H-tetrazole top
Crystal data top
[Fe2(C5H5)2(C20H16N8)]Z = 2
Mr = 610.29F(000) = 628
Triclinic, P1Dx = 1.492 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.9665 (3) ÅCell parameters from 2765 reflections
b = 11.0860 (2) Åθ = 2.8–27.5°
c = 12.9410 (3) ŵ = 1.10 mm−1
α = 74.982 (4)°T = 293 K
β = 67.793 (4)°Prism, colorless
γ = 70.738 (5)°0.25 × 0.15 × 0.10 mm
V = 1358.69 (8) Å3
Data collection top
Rigaku SCXmini
diffractometer		3375 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.071
graphiteθmax = 27.5°, θmin = 2.8°
Detector resolution: 13.6612 pixels mm-1h = −14→14
ω scansk = −14→14
13984 measured reflectionsl = −16→16
6158 independent reflections
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) = 0.117 w = 1/[σ2(Fo2) + (0.0405P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.95(Δ/σ)max < 0.001
6158 reflectionsΔρmax = 0.34 e Å−3
407 parametersΔρmin = −0.40 e Å−3
621 restraints
Crystal data top
[Fe2(C5H5)2(C20H16N8)]γ = 70.738 (5)°
Mr = 610.29V = 1358.69 (8) Å3
Triclinic, P1Z = 2
a = 10.9665 (3) ÅMo Kα radiation
b = 11.0860 (2) ŵ = 1.10 mm−1
c = 12.9410 (3) ÅT = 293 K
α = 74.982 (4)°0.25 × 0.15 × 0.10 mm
β = 67.793 (4)°
Data collection top
Rigaku SCXmini
diffractometer		3375 reflections with I > 2σ(I)
13984 measured reflectionsRint = 0.071
6158 independent reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.056?
wR(F2) = 0.117Δρmax = 0.34 e Å−3
S = 0.95Δρmin = −0.40 e Å−3
6158 reflectionsAbsolute structure: ?
407 parametersFlack parameter: ?
621 restraintsRogers parameter: ?
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
xyzUiso*/UeqOcc. (<1)
Fe10.58316 (5)0.73009 (5)0.09634 (4)0.04250 (16)
Fe2−0.12863 (5)1.12049 (5)0.23589 (5)0.04961 (17)
N10.3674 (3)0.4387 (3)0.4787 (3)0.0521 (8)
N20.2452 (3)0.4283 (3)0.5485 (2)0.0511 (8)
N30.3506 (3)0.5609 (3)0.4298 (2)0.0433 (7)
N40.2231 (3)0.6324 (3)0.4627 (2)0.0449 (7)
N5−0.3040 (3)0.9265 (3)0.5149 (3)0.0505 (8)
N6−0.3789 (3)0.9349 (4)0.6942 (3)0.0678 (10)
N7−0.4382 (4)1.0472 (4)0.6374 (3)0.0740 (11)
N8−0.3940 (3)1.0439 (3)0.5299 (3)0.0641 (9)
C10.6792 (4)0.8657 (4)−0.0129 (4)0.0667 (11)
H1B0.64480.9332−0.06850.080*
C20.7600 (5)0.7410 (5)−0.0309 (4)0.0745 (13)
H2B0.79340.7059−0.10160.089*
C30.7860 (4)0.6750 (4)0.0710 (5)0.0806 (14)
H3A0.84150.58640.08370.097*
C40.6553 (4)0.8767 (4)0.0987 (4)0.0712 (12)
H4B0.60100.95360.13480.085*
C50.7204 (5)0.7613 (5)0.1493 (4)0.0784 (13)
H5A0.72060.74260.22750.094*
C60.4641 (3)0.6131 (4)0.3473 (3)0.0461 (9)
H6A0.54970.54880.34550.055*
H6B0.46510.68870.37120.055*
C70.1593 (4)0.5462 (3)0.5371 (3)0.0414 (8)
C80.5128 (4)0.5690 (3)0.1457 (3)0.0471 (9)
H8A0.56790.47930.15250.057*
C90.4797 (4)0.6434 (4)0.0480 (3)0.0557 (10)
H9A0.50870.6143−0.02500.067*
C100.3811 (3)0.7707 (3)0.1868 (3)0.0471 (9)
H10A0.32970.84510.22680.057*
C110.4521 (3)0.6492 (3)0.2320 (3)0.0389 (8)
C120.3984 (4)0.7668 (4)0.0744 (3)0.0557 (10)
H12A0.36190.83850.02240.067*
C130.0124 (3)0.5768 (3)0.6002 (3)0.0403 (8)
C14−0.0457 (4)0.4852 (4)0.6813 (3)0.0531 (10)
H14A0.00870.40300.69700.064*
C15−0.1848 (4)0.5145 (4)0.7397 (3)0.0603 (11)
H15A−0.22360.45150.79250.072*
C16−0.0695 (3)0.6998 (3)0.5781 (3)0.0453 (9)
H16A−0.03130.76190.52340.054*
C17−0.2083 (4)0.7304 (4)0.6371 (3)0.0476 (9)
C18−0.2648 (4)0.6376 (4)0.7188 (3)0.0576 (10)
H18A−0.35720.65840.75980.069*
C19−0.2952 (4)0.8605 (4)0.6160 (3)0.0507 (9)
C20−0.2429 (4)0.8867 (3)0.4030 (3)0.0512 (9)
H20A−0.31180.91470.36580.061*
H20B−0.21270.79310.41170.061*
C21−0.1239 (4)0.9415 (3)0.3297 (3)0.0479 (9)
C22−0.0586 (4)0.9316 (4)0.2131 (3)0.0570 (10)
H22A−0.08550.89180.16850.068*
C230.0511 (4)0.9912 (4)0.1719 (4)0.0677 (11)
H23A0.11360.99920.09420.081*
C240.0544 (4)1.0356 (4)0.2636 (4)0.0656 (11)
H24A0.11921.08090.26030.079*
C25−0.0539 (4)1.0055 (4)0.3609 (4)0.0571 (10)
H25A−0.07651.02600.43630.069*
C26−0.262 (2)1.2163 (15)0.1517 (16)0.080 (4)0.609 (19)
H26A−0.28661.17840.10450.096*0.609 (19)
C27−0.153 (2)1.2725 (19)0.1138 (17)0.085 (5)0.609 (19)
H27A−0.09061.28020.03620.102*0.609 (19)
C28−0.3298 (12)1.2208 (12)0.2681 (16)0.064 (3)0.609 (19)
H28A−0.40971.18860.31600.077*0.609 (19)
C29−0.2581 (15)1.2829 (11)0.3010 (12)0.064 (3)0.609 (19)
H29A−0.27921.29800.37800.076*0.609 (19)
C30−0.1475 (16)1.3173 (12)0.2046 (17)0.075 (4)0.609 (19)
H30A−0.08221.36120.20250.090*0.609 (19)
C30'−0.132 (3)1.292 (3)0.126 (3)0.063 (4)0.391 (19)
H30B−0.05301.32230.07190.076*0.391 (19)
C28'−0.304 (2)1.256 (2)0.2895 (18)0.069 (6)0.391 (19)
H28B−0.36561.25590.36750.082*0.391 (19)
C29'−0.196 (3)1.310 (2)0.244 (3)0.070 (5)0.391 (19)
H29B−0.16861.35520.28380.084*0.391 (19)
C27'−0.207 (2)1.229 (2)0.1052 (17)0.065 (4)0.391 (19)
H27B−0.18501.20020.03330.079*0.391 (19)
C26'−0.3154 (16)1.2047 (19)0.204 (3)0.065 (5)0.391 (19)
H26B−0.38351.16080.21190.077*0.391 (19)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0497 (3)0.0375 (3)0.0420 (3)−0.0182 (2)−0.0125 (3)−0.0033 (2)
Fe20.0487 (3)0.0428 (3)0.0586 (4)−0.0086 (3)−0.0235 (3)−0.0045 (3)
N10.0493 (19)0.0487 (18)0.051 (2)−0.0080 (15)−0.0195 (16)0.0035 (15)
N20.053 (2)0.0471 (18)0.049 (2)−0.0168 (16)−0.0151 (16)0.0017 (15)
N30.0410 (17)0.0488 (18)0.0394 (17)−0.0135 (15)−0.0171 (14)0.0032 (14)
N40.0400 (17)0.0440 (17)0.0421 (18)−0.0092 (14)−0.0087 (14)−0.0017 (14)
N50.0438 (18)0.0413 (17)0.066 (2)−0.0079 (15)−0.0153 (16)−0.0151 (16)
N60.052 (2)0.075 (2)0.070 (2)−0.0050 (19)−0.0104 (19)−0.031 (2)
N70.058 (2)0.078 (3)0.082 (3)−0.004 (2)−0.012 (2)−0.038 (2)
N80.052 (2)0.053 (2)0.084 (3)−0.0044 (17)−0.018 (2)−0.0223 (19)
C10.071 (3)0.061 (2)0.064 (3)−0.037 (2)−0.012 (2)0.009 (2)
C20.075 (3)0.083 (3)0.062 (3)−0.046 (3)0.012 (2)−0.024 (2)
C30.047 (2)0.057 (3)0.119 (4)−0.015 (2)−0.017 (3)0.005 (2)
C40.075 (3)0.065 (3)0.077 (3)−0.041 (2)−0.001 (2)−0.022 (2)
C50.076 (3)0.115 (4)0.065 (3)−0.063 (3)−0.026 (2)0.007 (3)
C60.037 (2)0.057 (2)0.043 (2)−0.0168 (18)−0.0117 (17)−0.0018 (17)
C70.047 (2)0.046 (2)0.036 (2)−0.0186 (17)−0.0144 (16)−0.0042 (16)
C80.052 (2)0.0333 (17)0.053 (2)−0.0173 (16)−0.0106 (18)−0.0036 (16)
C90.084 (3)0.056 (2)0.042 (2)−0.037 (2)−0.022 (2)−0.0051 (17)
C100.0419 (19)0.0390 (19)0.060 (2)−0.0052 (16)−0.0199 (18)−0.0081 (17)
C110.0354 (19)0.0381 (18)0.0444 (19)−0.0103 (15)−0.0154 (15)−0.0033 (15)
C120.071 (3)0.047 (2)0.063 (3)−0.021 (2)−0.039 (2)0.0049 (19)
C130.0424 (19)0.049 (2)0.035 (2)−0.0189 (16)−0.0132 (16)−0.0040 (16)
C140.054 (2)0.054 (2)0.050 (2)−0.0217 (19)−0.0147 (19)0.0017 (18)
C150.061 (3)0.068 (3)0.047 (2)−0.035 (2)−0.007 (2)0.006 (2)
C160.045 (2)0.051 (2)0.044 (2)−0.0214 (17)−0.0119 (17)−0.0059 (17)
C170.045 (2)0.060 (2)0.043 (2)−0.0163 (18)−0.0133 (18)−0.0145 (18)
C180.049 (2)0.078 (3)0.044 (2)−0.027 (2)−0.0056 (19)−0.007 (2)
C190.040 (2)0.060 (2)0.049 (2)−0.0130 (18)−0.0058 (19)−0.0161 (19)
C200.054 (2)0.046 (2)0.058 (2)−0.0131 (18)−0.0181 (19)−0.0133 (18)
C210.041 (2)0.0422 (19)0.059 (2)−0.0066 (16)−0.0187 (17)−0.0065 (17)
C220.054 (2)0.048 (2)0.064 (3)−0.0078 (18)−0.014 (2)−0.0160 (19)
C230.049 (2)0.049 (2)0.080 (3)−0.0033 (17)−0.005 (2)−0.004 (2)
C240.043 (2)0.062 (3)0.090 (3)−0.0196 (19)−0.030 (2)0.011 (2)
C250.053 (2)0.056 (2)0.068 (2)−0.0150 (19)−0.034 (2)0.0041 (19)
C260.082 (10)0.079 (7)0.087 (9)0.009 (7)−0.060 (8)−0.015 (8)
C270.094 (9)0.061 (8)0.078 (5)−0.001 (6)−0.034 (6)0.011 (5)
C280.052 (4)0.052 (6)0.096 (9)−0.003 (3)−0.044 (5)−0.009 (5)
C290.067 (7)0.047 (5)0.085 (6)−0.002 (4)−0.038 (5)−0.020 (4)
C300.086 (8)0.038 (4)0.102 (11)−0.024 (5)−0.040 (7)0.013 (6)
C30'0.066 (8)0.053 (6)0.078 (8)−0.021 (5)−0.041 (6)0.013 (6)
C28'0.065 (8)0.052 (9)0.068 (8)0.009 (6)−0.020 (6)−0.007 (6)
C29'0.084 (12)0.045 (4)0.089 (11)−0.004 (6)−0.047 (9)−0.012 (7)
C27'0.061 (11)0.076 (9)0.064 (8)−0.017 (8)−0.031 (6)−0.002 (7)
C26'0.039 (7)0.061 (8)0.086 (14)−0.002 (6)−0.018 (8)−0.015 (9)
Geometric parameters (Å, °) top
Fe1—C112.020 (3)C8—H8A0.9800
Fe1—C32.021 (4)C9—C121.411 (5)
Fe1—C52.025 (4)C9—H9A0.9800
Fe1—C22.031 (4)C10—C121.404 (5)
Fe1—C82.034 (3)C10—C111.417 (4)
Fe1—C102.034 (3)C10—H10A0.9800
Fe1—C42.040 (4)C12—H12A0.9800
Fe1—C92.042 (4)C13—C141.381 (4)
Fe1—C122.045 (4)C13—C161.390 (5)
Fe1—C12.046 (4)C14—C151.389 (5)
Fe2—C29'2.00 (2)C14—H14A0.9300
Fe2—C262.005 (13)C15—C181.379 (5)
Fe2—C272.013 (19)C15—H15A0.9300
Fe2—C28'2.016 (19)C16—C171.389 (4)
Fe2—C212.036 (4)C16—H16A0.9300
Fe2—C232.036 (4)C17—C181.386 (5)
Fe2—C222.037 (4)C17—C191.467 (5)
Fe2—C252.040 (4)C18—H18A0.9300
Fe2—C292.040 (10)C20—C211.504 (5)
Fe2—C242.041 (4)C20—H20A0.9700
Fe2—C282.050 (11)C20—H20B0.9700
Fe2—C30'2.06 (3)C21—C251.413 (5)
N1—N31.322 (4)C21—C221.421 (5)
N1—N21.326 (4)C22—C231.424 (5)
N2—C71.346 (4)C22—H22A0.9800
N3—N41.326 (4)C23—C241.414 (6)
N3—C61.475 (4)C23—H23A0.9800
N4—C71.336 (4)C24—C251.422 (5)
N5—C191.345 (4)C24—H24A0.9800
N5—N81.358 (4)C25—H25A0.9800
N5—C201.464 (4)C26—C271.39 (2)
N6—C191.333 (4)C26—C281.413 (16)
N6—N71.366 (5)C26—H26A0.9800
N7—N81.294 (4)C27—C301.42 (2)
C1—C41.397 (6)C27—H27A0.9800
C1—C21.397 (6)C28—C291.427 (12)
C1—H1B0.9800C28—H28A0.9800
C2—C31.415 (6)C29—C301.445 (13)
C2—H2B0.9800C29—H29A0.9800
C3—C51.399 (6)C30—H30A0.9800
C3—H3A0.9800C30'—C27'1.38 (2)
C4—C51.376 (6)C30'—C29'1.46 (3)
C4—H4B0.9800C30'—H30B0.9800
C5—H5A0.9800C28'—C29'1.36 (3)
C6—C111.486 (4)C28'—C26'1.44 (2)
C6—H6A0.9700C28'—H28B0.9800
C6—H6B0.9700C29'—H29B0.9800
C7—C131.472 (4)C27'—C26'1.41 (2)
C8—C91.421 (5)C27'—H27B0.9800
C8—C111.428 (5)C26'—H26B0.9800
C11—Fe1—C3121.64 (17)C11—C6—H6A109.2
C11—Fe1—C5107.88 (16)N3—C6—H6B109.2
C3—Fe1—C540.47 (18)C11—C6—H6B109.2
C11—Fe1—C2157.84 (17)H6A—C6—H6B107.9
C3—Fe1—C240.87 (18)N4—C7—N2112.2 (3)
C5—Fe1—C267.80 (19)N4—C7—C13124.0 (3)
C11—Fe1—C841.26 (13)N2—C7—C13123.8 (3)
C3—Fe1—C8108.53 (17)C9—C8—C11107.6 (3)
C5—Fe1—C8125.84 (18)C9—C8—Fe169.9 (2)
C2—Fe1—C8122.32 (16)C11—C8—Fe168.85 (19)
C11—Fe1—C1040.91 (13)C9—C8—H8A126.2
C3—Fe1—C10156.7 (2)C11—C8—H8A126.2
C5—Fe1—C10121.13 (18)Fe1—C8—H8A126.2
C2—Fe1—C10160.30 (18)C12—C9—C8107.9 (3)
C8—Fe1—C1068.72 (14)C12—C9—Fe169.9 (2)
C11—Fe1—C4124.03 (16)C8—C9—Fe169.3 (2)
C3—Fe1—C467.56 (19)C12—C9—H9A126.0
C5—Fe1—C439.56 (17)C8—C9—H9A126.0
C2—Fe1—C467.42 (17)Fe1—C9—H9A126.0
C8—Fe1—C4161.55 (17)C12—C10—C11108.3 (3)
C10—Fe1—C4107.32 (16)C12—C10—Fe170.3 (2)
C11—Fe1—C968.95 (14)C11—C10—Fe169.01 (19)
C3—Fe1—C9125.8 (2)C12—C10—H10A125.8
C5—Fe1—C9162.9 (2)C11—C10—H10A125.8
C2—Fe1—C9108.41 (17)Fe1—C10—H10A125.8
C8—Fe1—C940.83 (14)C10—C11—C8107.6 (3)
C10—Fe1—C968.23 (15)C10—C11—C6126.1 (3)
C4—Fe1—C9156.12 (18)C8—C11—C6126.3 (3)
C11—Fe1—C1268.45 (14)C10—C11—Fe170.1 (2)
C3—Fe1—C12162.1 (2)C8—C11—Fe169.89 (19)
C5—Fe1—C12155.6 (2)C6—C11—Fe1124.2 (2)
C2—Fe1—C12124.69 (19)C10—C12—C9108.6 (3)
C8—Fe1—C1268.31 (15)C10—C12—Fe169.5 (2)
C10—Fe1—C1240.26 (14)C9—C12—Fe169.7 (2)
C4—Fe1—C12121.09 (18)C10—C12—H12A125.7
C9—Fe1—C1240.39 (14)C9—C12—H12A125.7
C11—Fe1—C1160.25 (16)Fe1—C12—H12A125.7
C3—Fe1—C167.90 (18)C14—C13—C16119.3 (3)
C5—Fe1—C167.10 (18)C14—C13—C7121.1 (3)
C2—Fe1—C140.09 (16)C16—C13—C7119.6 (3)
C8—Fe1—C1157.14 (16)C13—C14—C15120.7 (4)
C10—Fe1—C1123.77 (16)C13—C14—H14A119.6
C4—Fe1—C139.99 (16)C15—C14—H14A119.6
C9—Fe1—C1121.56 (17)C18—C15—C14119.6 (4)
C12—Fe1—C1107.73 (17)C18—C15—H15A120.2
C29'—Fe2—C2666.4 (9)C14—C15—H15A120.2
C29'—Fe2—C2750.0 (10)C17—C16—C13120.4 (3)
C26—Fe2—C2740.4 (6)C17—C16—H16A119.8
C29'—Fe2—C28'39.6 (7)C13—C16—H16A119.8
C26—Fe2—C28'53.2 (7)C18—C17—C16119.6 (4)
C27—Fe2—C28'68.0 (9)C18—C17—C19119.6 (3)
C29'—Fe2—C21143.7 (9)C16—C17—C19120.8 (3)
C26—Fe2—C21124.8 (6)C15—C18—C17120.4 (4)
C27—Fe2—C21161.4 (7)C15—C18—H18A119.8
C28'—Fe2—C21114.6 (7)C17—C18—H18A119.8
C29'—Fe2—C23138.0 (9)N6—C19—N5107.9 (4)
C26—Fe2—C23124.2 (5)N6—C19—C17125.7 (4)
C27—Fe2—C23108.3 (7)N5—C19—C17126.4 (3)
C28'—Fe2—C23176.3 (6)N5—C20—C21112.7 (3)
C21—Fe2—C2368.94 (15)N5—C20—H20A109.1
C29'—Fe2—C22175.1 (8)C21—C20—H20A109.1
C26—Fe2—C22109.9 (5)N5—C20—H20B109.1
C27—Fe2—C22125.1 (6)C21—C20—H20B109.1
C28'—Fe2—C22141.2 (9)H20A—C20—H20B107.8
C21—Fe2—C2240.83 (14)C25—C21—C22107.9 (3)
C23—Fe2—C2240.91 (15)C25—C21—C20128.5 (4)
C29'—Fe2—C25116.2 (8)C22—C21—C20123.6 (3)
C26—Fe2—C25159.7 (7)C25—C21—Fe269.9 (2)
C27—Fe2—C25157.2 (7)C22—C21—Fe269.6 (2)
C28'—Fe2—C25114.6 (7)C20—C21—Fe2127.8 (3)
C21—Fe2—C2540.58 (14)C21—C22—C23108.2 (4)
C23—Fe2—C2568.70 (17)C21—C22—Fe269.5 (2)
C22—Fe2—C2568.37 (16)C23—C22—Fe269.5 (2)
C29'—Fe2—C2924.4 (7)C21—C22—H22A125.9
C26—Fe2—C2967.8 (5)C23—C22—H22A125.9
C27—Fe2—C2968.1 (7)Fe2—C22—H22A125.9
C28'—Fe2—C2920.8 (7)C24—C23—C22107.5 (4)
C21—Fe2—C29121.4 (4)C24—C23—Fe269.9 (2)
C23—Fe2—C29158.4 (5)C22—C23—Fe269.6 (2)
C22—Fe2—C29158.4 (5)C24—C23—H23A126.2
C25—Fe2—C29105.9 (4)C22—C23—H23A126.2
C29'—Fe2—C24113.9 (8)Fe2—C23—H23A126.2
C26—Fe2—C24159.0 (7)C23—C24—C25108.4 (4)
C27—Fe2—C24122.2 (7)C23—C24—Fe269.5 (2)
C28'—Fe2—C24140.9 (9)C25—C24—Fe269.6 (2)
C21—Fe2—C2468.48 (15)C23—C24—H24A125.8
C23—Fe2—C2440.58 (17)C25—C24—H24A125.8
C22—Fe2—C2468.27 (17)Fe2—C24—H24A125.8
C25—Fe2—C2440.79 (14)C21—C25—C24108.0 (4)
C29—Fe2—C24121.9 (4)C21—C25—Fe269.6 (2)
C29'—Fe2—C2856.4 (7)C24—C25—Fe269.7 (2)
C26—Fe2—C2840.8 (4)C21—C25—H25A126.0
C27—Fe2—C2868.9 (7)C24—C25—H25A126.0
C28'—Fe2—C2820.1 (7)Fe2—C25—H25A126.0
C21—Fe2—C28107.0 (4)C27—C26—C28110.2 (12)
C23—Fe2—C28159.7 (5)C27—C26—Fe270.1 (9)
C22—Fe2—C28123.2 (4)C28—C26—Fe271.3 (7)
C25—Fe2—C28122.0 (5)C27—C26—H26A124.9
C29—Fe2—C2840.8 (3)C28—C26—H26A124.9
C24—Fe2—C28158.2 (6)Fe2—C26—H26A124.9
C29'—Fe2—C30'42.1 (10)C26—C27—C30109.5 (15)
C26—Fe2—C30'51.6 (8)C26—C27—Fe269.5 (9)
C27—Fe2—C30'12.8 (10)C30—C27—Fe271.8 (9)
C28'—Fe2—C30'68.3 (11)C26—C27—H27A125.2
C21—Fe2—C30'173.5 (10)C30—C27—H27A125.2
C23—Fe2—C30'108.0 (10)Fe2—C27—H27A125.2
C22—Fe2—C30'133.3 (10)C26—C28—C29105.3 (10)
C25—Fe2—C30'144.5 (8)C26—C28—Fe267.9 (7)
C29—Fe2—C30'63.5 (9)C29—C28—Fe269.2 (6)
C24—Fe2—C30'113.3 (7)C26—C28—H28A127.3
C28—Fe2—C30'73.8 (9)C29—C28—H28A127.3
N3—N1—N2105.9 (3)Fe2—C28—H28A127.3
N1—N2—C7106.2 (3)C28—C29—C30109.9 (11)
N1—N3—N4114.0 (3)C28—C29—Fe270.0 (6)
N1—N3—C6122.9 (3)C30—C29—Fe270.4 (6)
N4—N3—C6123.1 (3)C28—C29—H29A125.0
N3—N4—C7101.7 (3)C30—C29—H29A125.0
C19—N5—N8108.9 (3)Fe2—C29—H29A125.0
C19—N5—C20130.5 (3)C27—C30—C29105.0 (12)
N8—N5—C20120.4 (3)C27—C30—Fe267.6 (9)
C19—N6—N7105.9 (3)C29—C30—Fe268.4 (6)
N8—N7—N6111.1 (3)C27—C30—H30A127.5
N7—N8—N5106.3 (3)C29—C30—H30A127.5
C4—C1—C2107.9 (4)Fe2—C30—H30A127.5
C4—C1—Fe169.8 (2)C27'—C30'—C29'106 (2)
C2—C1—Fe169.4 (2)C27'—C30'—Fe272.2 (14)
C4—C1—H1B126.1C29'—C30'—Fe266.7 (13)
C2—C1—H1B126.1C27'—C30'—H30B127.0
Fe1—C1—H1B126.1C29'—C30'—H30B127.0
C1—C2—C3107.7 (4)Fe2—C30'—H30B127.0
C1—C2—Fe170.5 (2)C29'—C28'—C26'109.1 (16)
C3—C2—Fe169.2 (2)C29'—C28'—Fe269.5 (12)
C1—C2—H2B126.1C26'—C28'—Fe272.9 (11)
C3—C2—H2B126.1C29'—C28'—H28B125.5
Fe1—C2—H2B126.1C26'—C28'—H28B125.5
C5—C3—C2107.0 (4)Fe2—C28'—H28B125.5
C5—C3—Fe169.9 (3)C28'—C29'—C30'108.7 (18)
C2—C3—Fe169.9 (3)C28'—C29'—Fe271.0 (12)
C5—C3—H3A126.5C30'—C29'—Fe271.3 (14)
C2—C3—H3A126.5C28'—C29'—H29B125.6
Fe1—C3—H3A126.5C30'—C29'—H29B125.6
C5—C4—C1108.5 (4)Fe2—C29'—H29B125.6
C5—C4—Fe169.6 (2)C30'—C27'—C26'111 (2)
C1—C4—Fe170.2 (2)C30'—C27'—Fe269.2 (14)
C5—C4—H4B125.8C26'—C27'—Fe270.5 (11)
C1—C4—H4B125.8C30'—C27'—H27B124.7
Fe1—C4—H4B125.8C26'—C27'—H27B124.7
C4—C5—C3108.9 (4)Fe2—C27'—H27B124.7
C4—C5—Fe170.8 (3)C27'—C26'—C28'105.6 (16)
C3—C5—Fe169.6 (3)C27'—C26'—Fe270.2 (11)
C4—C5—H5A125.6C28'—C26'—Fe266.4 (11)
C3—C5—H5A125.6C27'—C26'—H26B127.2
Fe1—C5—H5A125.6C28'—C26'—H26B127.2
N3—C6—C11111.9 (3)Fe2—C26'—H26B127.2
N3—C6—H6A109.2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C20—H20B···N2i0.972.493.391 (5)154
Symmetry codes: (i) −x, −y+1, −z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C20—H20B···N2i0.972.493.391 (5)154
Symmetry codes: (i) −x, −y+1, −z+1.
Acknowledgements top

This work was supported by a start-up grant from Southeast University.

references
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