Literature DB >> 22807762

Dicarbon-yl(hexa-methyl-ene-1,3,5,7-tetra-mine-κN(1))(η(5)-penta-methyl-cyclo-penta-dien-yl)iron(II) tetra-fluoridoborate.

Cyprian M M'thiruaine, Holger B Friedrich, Evans O Changamu, Manuel A Fernandes.   

Abstract

In the title compound, [Fe(C(10)H(15))(C(6)H(12)N(4))(CO)(2)]BF(4), the arrangement around the Fe(II) atom corresponds to a three-legged piano stool. The penta-methyl-cyclo-penta-dienyl (Cp*) ligand occupies three coordination sites, while two CO ligands and one N atom of the hexa-methyl-ene-tetra-mine ligand occupy the remaining coordination sites, completing a pseudo-octahedral geometry. Both the complex cation and the BF(4) (-) anion reside on crystallographic mirror planes. The Fe-N bond length is 2.069 (2) and the Fe-Cp*(centroid) distance is 1.7452 (3) Å.

Entities:  

Year:  2012        PMID： 22807762      PMCID： PMC3393194          DOI： 10.1107/S1600536812026360

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For the synthesis of the title compound and structure of the dinuclear compound [Fe2(η5-C5H5)2{N4(CH2)6}(CO)4](BF4)2 see: M’thiruaine et al. (2012. For other related compounds, see: Allan et al. (1970 ▶); Darensbourg et al. (2003 ▶); Lu et al. (2004 ▶); Matos & Verkade (2003 ▶); M’thiruaine et al. (2012b ▶); Shafiq et al. (2000 ▶). For mol­ecular structures of other metal complexes of hexa­methyl­ene­tetra­mine, see: Zheng et al. (2008 ▶); Xue et al. (2009 ▶). For applications of hexa­methyl­ene­tetra­mine, see: Greenwood (1981 ▶); Strom & Jun (1986 ▶); Garcia et al. (2010 ▶).

Experimental

Crystal data

[Fe(C10H15)(C6H12N4)(CO)2]BF4 M = 474.10 Orthorhombic, a = 13.8388 (6) Å b = 9.1771 (4) Å c = 16.4365 (8) Å V = 2087.44 (16) Å3 Z = 4 Mo Kα radiation μ = 0.78 mm−1 T = 173 K 0.40 × 0.40 × 0.40 mm

Data collection

Bruker APEXII CCD diffractometer Absorption correction: integration (SADABS; Bruker, 2005 ▶) T min = 0.746, T max = 0.746 16663 measured reflections 2671 independent reflections 2065 reflections with I > 2σ(I) R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.033 wR(F 2) = 0.094 S = 1.04 2671 reflections 153 parameters H-atom parameters constrained Δρmax = 0.56 e Å−3 Δρmin = −0.55 e Å−3 Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT-Plus (Bruker, 2005 ▶); data reduction: SAINT-Plus and XPREP (Bruker, 2005 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 Farrugia (1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶). Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812026360/fj2565sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812026360/fj2565Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Fe(C10H15)(C6H12N4)(CO)2]BF4F(000) = 984
Mr = 474.10Dx = 1.509 Mg m−3
Orthorhombic, PnmaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2nCell parameters from 4126 reflections
a = 13.8388 (6) Åθ = 2.5–26.9°
b = 9.1771 (4) ŵ = 0.78 mm−1
c = 16.4365 (8) ÅT = 173 K
V = 2087.44 (16) Å3Block, brown
Z = 40.40 × 0.40 × 0.40 mm
Bruker APEXII CCD diffractometer2671 independent reflections
Radiation source: fine-focus sealed tube2065 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.050
φ and ω scansθmax = 28.0°, θmin = 1.9°
Absorption correction: integration (SADABS; Bruker, 2005)h = −17→18
Tmin = 0.746, Tmax = 0.746k = −12→12
16663 measured reflectionsl = −14→21
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0514P)2] where P = (Fo2 + 2Fc2)/3
2671 reflections(Δ/σ)max = 0.008
153 parametersΔρmax = 0.56 e Å−3
0 restraintsΔρmin = −0.55 e Å−3
Experimental. face indexed absorption corrections carried out with XPREP; Bruker, 2005)
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.
xyzUiso*/UeqOcc. (<1)
C1−0.07473 (16)0.75000.29615 (16)0.0216 (5)
C2−0.04858 (13)0.8758 (2)0.25029 (10)0.0225 (4)
C3−0.01373 (12)0.82727 (19)0.17274 (10)0.0239 (4)
C4−0.13130 (18)0.75000.37414 (16)0.0286 (6)
H4A−0.11610.66600.40520.043*0.50
H4B−0.19850.75000.36290.043*
H4C−0.11610.83400.40520.043*0.50
C5−0.06466 (14)1.0313 (2)0.27470 (13)0.0304 (4)
H5A−0.12291.06850.24780.046*
H5B−0.00881.09000.25840.046*
H5C−0.07281.03700.33380.046*
C60.00822 (15)0.9225 (2)0.10053 (12)0.0351 (5)
H6A0.06010.87830.06830.053*
H6B0.02871.01900.11940.053*
H6C−0.04990.93240.06680.053*
C70.15593 (13)0.6020 (2)0.23589 (11)0.0263 (4)
C80.09551 (13)0.61629 (18)0.43011 (11)0.0220 (4)
H8A0.02400.61200.42980.026*
H8B0.12000.52800.40230.026*
C90.23775 (17)0.75000.38815 (15)0.0238 (5)
H9A0.26290.66280.35970.029*0.50
H9B0.26290.83720.35970.029*0.50
C100.23601 (14)0.61969 (19)0.51331 (11)0.0295 (4)
H10A0.26010.61860.57000.035*
H10B0.26060.53130.48570.035*
C110.0944 (2)0.75000.55398 (16)0.0278 (6)
H11A0.11600.75000.61140.033*
H11B0.02280.75000.55370.033*
B10.2554 (3)0.25000.4092 (2)0.0361 (8)
F10.28284 (11)0.12563 (13)0.36756 (8)0.0570 (4)
F20.29634 (17)0.25000.48627 (13)0.0660 (6)
F30.15679 (15)0.25000.41946 (15)0.0703 (7)
Fe10.07875 (2)0.75000.26471 (2)0.01882 (12)
N10.12822 (14)0.75000.38349 (12)0.0187 (4)
N20.12944 (12)0.61662 (15)0.51387 (9)0.0253 (3)
N30.27327 (16)0.75000.47139 (13)0.0269 (5)
O10.19858 (10)0.50678 (17)0.21102 (9)0.0410 (4)
U11U22U33U12U13U23
C10.0185 (12)0.0302 (13)0.0161 (12)0.000−0.0015 (9)0.000
C20.0204 (9)0.0277 (9)0.0194 (9)0.0024 (7)−0.0024 (7)0.0002 (7)
C30.0224 (9)0.0318 (10)0.0174 (9)0.0007 (7)−0.0027 (7)0.0037 (7)
C40.0205 (13)0.0430 (16)0.0223 (14)0.0000.0035 (11)0.000
C50.0316 (11)0.0271 (9)0.0326 (12)0.0070 (8)−0.0011 (8)−0.0017 (8)
C60.0375 (11)0.0463 (12)0.0216 (10)−0.0025 (9)−0.0019 (8)0.0118 (9)
C70.0247 (10)0.0361 (10)0.0182 (9)0.0006 (8)−0.0031 (7)−0.0028 (8)
C80.0296 (10)0.0189 (8)0.0177 (9)−0.0013 (7)−0.0010 (7)0.0008 (7)
C90.0197 (12)0.0320 (13)0.0198 (13)0.000−0.0020 (10)0.000
C100.0377 (11)0.0289 (10)0.0219 (10)0.0049 (8)−0.0073 (8)0.0024 (8)
C110.0410 (16)0.0265 (13)0.0158 (13)0.0000.0015 (11)0.000
B10.045 (2)0.0277 (15)0.036 (2)0.0000.0101 (15)0.000
F10.0836 (11)0.0364 (7)0.0509 (9)0.0058 (7)0.0261 (7)−0.0094 (6)
F20.0916 (17)0.0588 (13)0.0476 (13)0.000−0.0102 (12)0.000
F30.0478 (13)0.0654 (14)0.0979 (19)0.0000.0209 (12)0.000
Fe10.0191 (2)0.02309 (19)0.01423 (19)0.0000.00091 (13)0.000
N10.0216 (10)0.0195 (10)0.0151 (10)0.0000.0006 (8)0.000
N20.0361 (9)0.0220 (7)0.0178 (8)0.0003 (6)−0.0030 (6)0.0009 (6)
N30.0295 (12)0.0298 (11)0.0213 (11)0.000−0.0066 (9)0.000
O10.0396 (8)0.0480 (9)0.0354 (8)0.0173 (7)−0.0028 (7)−0.0147 (7)
C1—C21.425 (2)C8—H8B0.9900
C1—C2i1.425 (2)C9—N31.454 (3)
C1—C41.502 (3)C9—N11.518 (3)
C1—Fe12.186 (2)C9—H9A0.9900
C2—C31.434 (2)C9—H9B0.9900
C2—C51.499 (2)C10—N31.473 (2)
C2—Fe12.1199 (18)C10—N21.475 (3)
C3—C3i1.418 (3)C10—H10A0.9900
C3—C61.505 (2)C10—H10B0.9900
C3—Fe12.1038 (17)C11—N21.473 (2)
C4—H4A0.9482C11—N2i1.473 (2)
C4—H4B0.9477C11—H11A0.9900
C4—H4C0.9482C11—H11B0.9900
C5—H5A0.9800B1—F31.375 (4)
C5—H5B0.9800B1—F1ii1.384 (2)
C5—H5C0.9800B1—F11.384 (2)
C6—H6A0.9800B1—F21.388 (4)
C6—H6B0.9800Fe1—C7i1.791 (2)
C6—H6C0.9800Fe1—N12.069 (2)
C7—O11.131 (2)Fe1—C3i2.1038 (17)
C7—Fe11.791 (2)Fe1—C2i2.1199 (18)
C8—N21.455 (2)N1—C8i1.516 (2)
C8—N11.516 (2)N3—C10i1.473 (2)
C8—H8A0.9900
C2—C1—C2i108.2 (2)H10A—C10—H10B108.0
C2—C1—C4125.70 (11)N2—C11—N2i112.4 (2)
C2i—C1—C4125.70 (11)N2—C11—H11A109.1
C2—C1—Fe168.18 (12)N2i—C11—H11A109.1
C2i—C1—Fe168.18 (12)N2—C11—H11B109.1
C4—C1—Fe1135.09 (18)N2i—C11—H11B109.1
C1—C2—C3107.69 (16)H11A—C11—H11B107.8
C1—C2—C5126.29 (17)F3—B1—F1ii109.5 (2)
C3—C2—C5125.70 (16)F3—B1—F1109.5 (2)
C1—C2—Fe173.19 (12)F1ii—B1—F1111.1 (3)
C3—C2—Fe169.55 (10)F3—B1—F2107.1 (3)
C5—C2—Fe1127.73 (13)F1ii—B1—F2109.8 (2)
C3i—C3—C2108.09 (10)F1—B1—F2109.8 (2)
C3i—C3—C6125.52 (11)C7—Fe1—C7i98.58 (12)
C2—C3—C6126.05 (16)C7—Fe1—N193.00 (7)
C3i—C3—Fe170.30 (5)C7i—Fe1—N193.00 (7)
C2—C3—Fe170.76 (10)C7—Fe1—C3i85.25 (8)
C6—C3—Fe1129.76 (13)C7i—Fe1—C3i115.35 (8)
C1—C4—H4A110.1N1—Fe1—C3i151.56 (6)
C1—C4—H4B110.2C7—Fe1—C3115.35 (8)
H4A—C4—H4B108.8C7i—Fe1—C385.25 (8)
C1—C4—H4C110.1N1—Fe1—C3151.56 (6)
H4A—C4—H4C108.8C3i—Fe1—C339.40 (10)
H4B—C4—H4C108.8C7—Fe1—C2i93.05 (8)
C2—C5—H5A109.5C7i—Fe1—C2i151.50 (8)
C2—C5—H5B109.5N1—Fe1—C2i112.37 (7)
H5A—C5—H5B109.5C3i—Fe1—C2i39.69 (7)
C2—C5—H5C109.5C3—Fe1—C2i66.27 (7)
H5A—C5—H5C109.5C7—Fe1—C2151.50 (8)
H5B—C5—H5C109.5C7i—Fe1—C293.05 (8)
C3—C6—H6A109.5N1—Fe1—C2112.37 (7)
C3—C6—H6B109.5C3i—Fe1—C266.27 (7)
H6A—C6—H6B109.5C3—Fe1—C239.69 (7)
C3—C6—H6C109.5C2i—Fe1—C265.99 (10)
H6A—C6—H6C109.5C7—Fe1—C1129.93 (6)
H6B—C6—H6C109.5C7i—Fe1—C1129.93 (6)
O1—C7—Fe1172.94 (17)N1—Fe1—C195.65 (9)
N2—C8—N1112.36 (14)C3i—Fe1—C165.09 (8)
N2—C8—H8A109.1C3—Fe1—C165.09 (8)
N1—C8—H8A109.1C2i—Fe1—C138.62 (6)
N2—C8—H8B109.1C2—Fe1—C138.62 (6)
N1—C8—H8B109.1C8i—N1—C8108.09 (18)
H8A—C8—H8B107.9C8i—N1—C9105.83 (12)
N3—C9—N1112.7 (2)C8—N1—C9105.83 (12)
N3—C9—H9A109.1C8i—N1—Fe1112.22 (10)
N1—C9—H9A109.1C8—N1—Fe1112.22 (10)
N3—C9—H9B109.1C9—N1—Fe1112.21 (14)
N1—C9—H9B109.1C8—N2—C11108.61 (16)
H9A—C9—H9B107.8C8—N2—C10108.47 (14)
N3—C10—N2111.61 (15)C11—N2—C10108.45 (16)
N3—C10—H10A109.3C9—N3—C10i108.77 (13)
N2—C10—H10A109.3C9—N3—C10108.77 (13)
N3—C10—H10B109.3C10i—N3—C10108.5 (2)
N2—C10—H10B109.3
C2i—C1—C2—C34.9 (3)C2i—C1—Fe1—C7−20.56 (17)
C4—C1—C2—C3−168.0 (2)C4—C1—Fe1—C798.70 (10)
Fe1—C1—C2—C361.35 (13)C2—C1—Fe1—C7i20.56 (17)
C2i—C1—C2—C5178.72 (12)C2i—C1—Fe1—C7i142.04 (11)
C4—C1—C2—C55.8 (4)C4—C1—Fe1—C7i−98.70 (10)
Fe1—C1—C2—C5−124.84 (19)C2—C1—Fe1—N1119.26 (11)
C2i—C1—C2—Fe1−56.44 (17)C2i—C1—Fe1—N1−119.26 (11)
C4—C1—C2—Fe1130.7 (2)C4—C1—Fe1—N10.0
C1—C2—C3—C3i−3.03 (16)C2—C1—Fe1—C3i−82.56 (13)
C5—C2—C3—C3i−176.89 (15)C2i—C1—Fe1—C3i38.92 (11)
Fe1—C2—C3—C3i60.69 (12)C4—C1—Fe1—C3i158.18 (5)
C1—C2—C3—C6170.56 (18)C2—C1—Fe1—C3−38.92 (11)
C5—C2—C3—C6−3.3 (3)C2i—C1—Fe1—C382.56 (13)
Fe1—C2—C3—C6−125.73 (18)C4—C1—Fe1—C3−158.18 (5)
C1—C2—C3—Fe1−63.71 (14)C2—C1—Fe1—C2i−121.5 (2)
C5—C2—C3—Fe1122.43 (19)C4—C1—Fe1—C2i119.26 (11)
C3i—C3—Fe1—C743.83 (7)C2i—C1—Fe1—C2121.5 (2)
C2—C3—Fe1—C7162.15 (11)C4—C1—Fe1—C2−119.26 (11)
C6—C3—Fe1—C7−76.48 (19)N2—C8—N1—C8i−55.2 (2)
C3i—C3—Fe1—C7i141.10 (6)N2—C8—N1—C957.82 (19)
C2—C3—Fe1—C7i−100.59 (12)N2—C8—N1—Fe1−179.48 (11)
C6—C3—Fe1—C7i20.78 (18)N3—C9—N1—C8i57.29 (11)
C3i—C3—Fe1—N1−131.39 (13)N3—C9—N1—C8−57.29 (11)
C2—C3—Fe1—N1−13.07 (18)N3—C9—N1—Fe1180.0
C6—C3—Fe1—N1108.29 (19)C7—Fe1—N1—C8i168.40 (13)
C2—C3—Fe1—C3i118.32 (9)C7i—Fe1—N1—C8i69.64 (13)
C6—C3—Fe1—C3i−120.32 (16)C3i—Fe1—N1—C8i−106.04 (13)
C3i—C3—Fe1—C2i−37.89 (6)C3—Fe1—N1—C8i−15.9 (2)
C2—C3—Fe1—C2i80.43 (14)C2i—Fe1—N1—C8i−97.06 (12)
C6—C3—Fe1—C2i−158.20 (19)C2—Fe1—N1—C8i−24.90 (14)
C3i—C3—Fe1—C2−118.32 (9)C1—Fe1—N1—C8i−60.98 (12)
C6—C3—Fe1—C2121.4 (2)C7—Fe1—N1—C8−69.64 (13)
C3i—C3—Fe1—C1−80.43 (9)C7i—Fe1—N1—C8−168.40 (13)
C2—C3—Fe1—C137.89 (9)C3i—Fe1—N1—C815.9 (2)
C6—C3—Fe1—C1159.25 (19)C3—Fe1—N1—C8106.04 (13)
C1—C2—Fe1—C781.4 (2)C2i—Fe1—N1—C824.90 (14)
C3—C2—Fe1—C7−35.5 (2)C2—Fe1—N1—C897.06 (12)
C5—C2—Fe1—C7−155.42 (17)C1—Fe1—N1—C860.98 (12)
C1—C2—Fe1—C7i−164.35 (13)C7—Fe1—N1—C949.38 (6)
C3—C2—Fe1—C7i78.81 (12)C7i—Fe1—N1—C9−49.38 (6)
C5—C2—Fe1—C7i−41.12 (17)C3i—Fe1—N1—C9134.94 (12)
C1—C2—Fe1—N1−69.85 (12)C3—Fe1—N1—C9−134.94 (12)
C3—C2—Fe1—N1173.31 (9)C2i—Fe1—N1—C9143.92 (6)
C5—C2—Fe1—N153.38 (17)C2—Fe1—N1—C9−143.92 (6)
C1—C2—Fe1—C3i79.22 (12)C1—Fe1—N1—C9180.0
C3—C2—Fe1—C3i−37.62 (11)N1—C8—N2—C1157.6 (2)
C5—C2—Fe1—C3i−157.54 (18)N1—C8—N2—C10−60.06 (18)
C1—C2—Fe1—C3116.84 (16)N2i—C11—N2—C8−60.0 (3)
C5—C2—Fe1—C3−119.9 (2)N2i—C11—N2—C1057.7 (2)
C1—C2—Fe1—C2i35.65 (13)N3—C10—N2—C859.72 (18)
C3—C2—Fe1—C2i−81.19 (10)N3—C10—N2—C11−58.1 (2)
C5—C2—Fe1—C2i158.88 (14)N1—C9—N3—C10i−59.01 (14)
C3—C2—Fe1—C1−116.84 (16)N1—C9—N3—C1059.01 (14)
C5—C2—Fe1—C1123.2 (2)N2—C10—N3—C9−59.2 (2)
C2—C1—Fe1—C7−142.04 (11)N2—C10—N3—C10i59.0 (2)
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1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  Separation and quantitation of methenamine in urine by ion-pair extraction.

Authors:  J G Strom; H W Jun
Journal:  J Pharm Sci       Date:  1986-04       Impact factor: 3.534

3.  The antibacterial activity of hexamine (methenamine), hexamine hippurate and hexamine mandelate.

Authors:  D Greenwood; R C Slack
Journal:  Infection       Date:  1981       Impact factor: 3.553

4.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
  4 in total
  1 in total

1.  Dicarbon-yl(η(5)-cyclo-penta-dien-yl)(hexa-methyl-enetetra-mine-κN(1))iron(II) tetra-fluoridoborate.

Authors:  Cyprian M M'thiruaine; Holger B Friedrich; Bernard Omondi
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-07-18
  1 in total

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