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Acta Crystallogr Sect E Struct Rep Online. 2009 July 1; 65(Pt 7): m835.
Published online 2009 June 27. doi:  10.1107/S1600536809023575
PMCID: PMC2969406

(S)-1-(1-Ferrocenylmethyl-1H-benz­imidazol-2-yl)ethanol monohydrate

Abstract

In the structure of the title compound, [Fe(C5H5)(C15H15N2O)]·H2O, the unsubstituted cyclo­penta­diene (Cp) ring is disordered over two positions, with site-occupancy factors of 0.636 (12) and 0.364 (12). The dihedral angles between the planes of the substituted Cp ring and the major and minor components of the disordered ring are 0.8 (3) and 3.4 (6)°, respectively. The crystal packing is stabilized by inter­molecular O—H(...)O hydrogen bonds, forming zigzag chains running parallel to the a axis.

Related literature

For applications of ferrocene compounds, see: Savage et al. (2006 [triangle]); Carr et al. (2001 [triangle]). For the biological and pharmaceutical activity of imidazole and benzimidazole derivatives, see: Matsuno et al. (2000 [triangle]); Garuti et al. (1999 [triangle]). For the synthesis and crystal structure of (±)-1-(1H-benzimidazol-2-yl)ethanol, see: Xia & Xu (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0m835-scheme1.jpg

Experimental

Crystal data

  • [Fe(C5H5)(C15H15N2O)]·H2O
  • M r = 378.25
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m835-efi1.jpg
  • a = 7.678 (5) Å
  • b = 12.480 (8) Å
  • c = 19.428 (12) Å
  • V = 1862 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.83 mm−1
  • T = 293 K
  • 0.40 × 0.35 × 0.30 mm

Data collection

  • Rigaku SCXmini diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 [triangle]) T min = 0.724, T max = 0.785
  • 19049 measured reflections
  • 4236 independent reflections
  • 3622 reflections with I > 2σ(I)
  • R int = 0.042

Refinement

  • R[F 2 > 2σ(F 2)] = 0.043
  • wR(F 2) = 0.113
  • S = 1.05
  • 4236 reflections
  • 243 parameters
  • 146 restraints
  • H-atom parameters constrained
  • Δρmax = 0.32 e Å−3
  • Δρmin = −0.21 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 1811 Friedel pairs
  • Flack parameter: 0.03 (2)

Data collection: CrystalClear (Rigaku, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809023575/rz2334sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809023575/rz2334Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

Financial support by the start-up fund of Southeast University is gratefully acknowledged.

supplementary crystallographic information

Comment

The organometallic compound ferrocene has found several novel applications due to its stability, spectroscopic properties, electrochemical properties and ease of use (Savage et al., 2006). The ferrocene unit can affect the properties of the binding site and likewise binding event can affect the properties of ferrocene (Carr et al., 2001). Imidazole and benzimidazole derivatives are important heteroaromatic compounds and have attracted considerable attention because of their good biological and pharmaceutical activities (Matsuno et al., 2000; Garuti et al., 1999).

In the title compound (Fig. 1), the unsubstituted cyclopentadiene (Cp) ring is disordered over two positions, with site-occupancy factors of 0.636 (12) and 0.364 (12) for the major and minor components respectively. The dihedral angles between the substituted Cp ring and the major and minor components of the disordered ring are 0.8 (3)° and 3.4 (6)°, respectively. All bond lengths and angels are normal. The dihedral angle between the benzimidazole ring system and the substituted Cp ring is 72.92 (9)°. In the crystal structure (Fig. 2), the molecules are connected through intermolecular O—H···O hydrogen bonds (Table 1) to form zigzag chains running parallel to the a axis.

Experimental

The title compound was synthesized by the reaction of L-(-)-1-(1H-benzimidazol-2-yl)ethanol (10 mmol) with a solution of FeCH2N+(CH3)3I- (10 mmol) in water (20 ml) at 105 °C. L-(-)-1-(1H-Benzimidazol-2-yl)ethanol was synthesized by the reaction of benzene-1,2-diamine and ethyl L-(-)-lactate at 115°C according to the literature method (Xia & Xu, 2008). Crystals suitable for X-ray diffraction analysis were obtained by slow evaporation of a methanol solution at room temperature over a period of one week.

Refinement

All H atoms were fixed geometrically and treated as riding, with C—H = 0.93-0.98 Å, O—H = 0.82-0.85 Å and with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(C, O) for methyl, hydroxyl and water H atoms. The C1—C5 cyclopentadiene ring is disordered over two positions, with refined site-occupancy factors of 0.636 (12) and 0.364 (12) for the major and minor components respectively. During the refinement of the disordered cyclopentadiene ring, soft proximity (SIMU) and rigid-bond restraints (DELU) were applied to the anisotropic displacement parameters.

Figures

Fig. 1.
The molecular structure of the title compound with the atomic numbering scheme. Displacement ellipsoids were drawn at the 30% probability level. Only the major component of disorder is shown.
Fig. 2.
Packing diagram of the title compound viewed along the a axis. Intermolecular O—H···O hydrogen bonds are shown as dashed lines.

Crystal data

[Fe(C5H5)(C15H15N2O)]·H2OF(000) = 792
Mr = 378.25Dx = 1.349 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 4425 reflections
a = 7.678 (5) Åθ = 2.7–27.5°
b = 12.480 (8) ŵ = 0.83 mm1
c = 19.428 (12) ÅT = 293 K
V = 1862 (2) Å3Block, colourless
Z = 40.40 × 0.35 × 0.30 mm

Data collection

Rigaku SCXmini diffractometer4236 independent reflections
Radiation source: fine-focus sealed tube3622 reflections with I > 2σ(I)
graphiteRint = 0.042
Detector resolution: 13.6612 pixels mm-1θmax = 27.5°, θmin = 2.7°
ω scansh = −9→9
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)k = −16→16
Tmin = 0.724, Tmax = 0.785l = −25→25
19049 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.113w = 1/[σ2(Fo2) + (0.0566P)2 + 0.1498P] where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
4236 reflectionsΔρmax = 0.32 e Å3
243 parametersΔρmin = −0.21 e Å3
146 restraintsAbsolute structure: Flack (1983), 1811 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.03 (2)

Special details

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)

xyzUiso*/UeqOcc. (<1)
Fe10.12377 (5)0.11965 (3)0.10136 (2)0.05548 (14)
C10.2965 (13)0.2388 (10)0.0874 (6)0.076 (2)0.636 (12)
H10.30400.30180.11280.092*0.636 (12)
C20.3868 (13)0.1411 (10)0.1064 (6)0.088 (2)0.636 (12)
H20.45820.13090.14450.105*0.636 (12)
C30.3440 (15)0.0626 (9)0.0545 (6)0.090 (2)0.636 (12)
H30.3799−0.00850.05190.108*0.636 (12)
C40.2340 (16)0.1193 (11)0.0081 (5)0.087 (2)0.636 (12)
H40.18880.0883−0.03160.104*0.636 (12)
C50.198 (2)0.2298 (13)0.0278 (7)0.081 (2)0.636 (12)
H50.12780.28050.00630.097*0.636 (12)
C1'0.344 (2)0.218 (2)0.0982 (13)0.076 (2)0.364 (12)
H1'0.38150.26280.13330.092*0.364 (12)
C2'0.384 (3)0.104 (2)0.0815 (11)0.088 (2)0.364 (12)
H2'0.45990.05940.10590.105*0.364 (12)
C3'0.294 (3)0.0763 (17)0.0258 (12)0.090 (2)0.364 (12)
H3'0.30240.00820.00680.108*0.364 (12)
C4'0.187 (3)0.1529 (19)−0.0023 (11)0.087 (2)0.364 (12)
H4'0.10920.1521−0.03910.104*0.364 (12)
C5'0.236 (4)0.233 (2)0.0447 (15)0.081 (2)0.364 (12)
H5'0.19040.30090.03840.097*0.364 (12)
C60.0499 (5)0.0507 (3)0.19164 (17)0.0656 (8)
H60.12260.02770.22700.079*
C7−0.0067 (6)−0.0118 (3)0.1347 (2)0.0781 (10)
H70.0243−0.08250.12600.094*
C8−0.1161 (5)0.0507 (3)0.09454 (18)0.0714 (8)
H8−0.17170.02860.05440.086*
C9−0.1290 (4)0.1537 (3)0.12467 (16)0.0617 (7)
H9−0.19430.21080.10800.074*
C10−0.0239 (3)0.1541 (2)0.18508 (14)0.0490 (6)
C11−0.0006 (4)0.2455 (2)0.23385 (14)0.0553 (7)
H11A0.09890.23170.26330.066*
H11B0.02260.31050.20810.066*
C12−0.2966 (4)0.3248 (2)0.25873 (14)0.0531 (7)
C13−0.3238 (4)0.3941 (3)0.20362 (16)0.0636 (8)
H13A−0.24370.40090.16800.076*
C14−0.4778 (5)0.4525 (3)0.2051 (2)0.0791 (11)
H14A−0.50030.50080.16980.095*
C15−0.6005 (6)0.4410 (4)0.2581 (2)0.0918 (12)
H15A−0.70200.48180.25710.110*
C16−0.5738 (5)0.3712 (4)0.3111 (2)0.0827 (10)
H16A−0.65650.36280.34570.099*
C17−0.4184 (4)0.3126 (3)0.31211 (16)0.0632 (8)
C18−0.1993 (4)0.2124 (3)0.33753 (15)0.0601 (7)
C19−0.0719 (5)0.1412 (3)0.37575 (19)0.0757 (10)
H19A−0.00510.10040.34170.091*
C20−0.1628 (7)0.0627 (4)0.4224 (3)0.1130 (17)
H20A−0.07780.01860.44510.169*
H20B−0.23930.01830.39570.169*
H20C−0.22920.10110.45630.169*
N1−0.1568 (3)0.2606 (2)0.27640 (11)0.0538 (6)
N2−0.3554 (4)0.2401 (2)0.36061 (13)0.0683 (7)
O10.0467 (4)0.2076 (3)0.41300 (18)0.0971 (9)
H1''0.14410.18080.41200.146*
OW0.4102 (5)0.1890 (3)0.47061 (15)0.1251 (12)
HWB0.44400.25350.47460.188*
HWC0.39480.16210.51040.188*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Fe10.0499 (2)0.0611 (2)0.0554 (2)0.0041 (2)0.01120 (19)0.0056 (2)
C10.042 (5)0.101 (5)0.086 (5)−0.012 (3)0.007 (4)0.018 (4)
C20.051 (2)0.129 (7)0.084 (6)0.007 (4)0.017 (4)0.021 (4)
C30.072 (6)0.119 (4)0.079 (6)0.029 (3)0.028 (4)0.005 (4)
C40.079 (7)0.124 (7)0.058 (4)0.009 (4)0.019 (3)0.016 (4)
C50.068 (7)0.104 (3)0.071 (7)−0.004 (4)0.012 (3)0.029 (4)
C1'0.042 (5)0.101 (5)0.086 (5)−0.012 (3)0.007 (4)0.018 (4)
C2'0.051 (2)0.129 (7)0.084 (6)0.007 (4)0.017 (4)0.021 (4)
C3'0.072 (6)0.119 (4)0.079 (6)0.029 (3)0.028 (4)0.005 (4)
C4'0.079 (7)0.124 (7)0.058 (4)0.009 (4)0.019 (3)0.016 (4)
C5'0.068 (7)0.104 (3)0.071 (7)−0.004 (4)0.012 (3)0.029 (4)
C60.0729 (19)0.0610 (17)0.0627 (18)0.0124 (15)0.0137 (16)0.0162 (15)
C70.099 (3)0.0551 (18)0.081 (2)−0.0086 (19)0.025 (2)−0.0063 (17)
C80.0674 (19)0.083 (2)0.0638 (18)−0.0155 (18)−0.002 (2)−0.0108 (17)
C90.0454 (14)0.083 (2)0.0564 (15)0.0054 (15)−0.0020 (13)−0.0046 (14)
C100.0421 (13)0.0572 (15)0.0476 (13)0.0021 (11)0.0044 (11)0.0056 (12)
C110.0479 (14)0.0623 (17)0.0559 (17)0.0006 (13)−0.0042 (12)0.0015 (14)
C120.0512 (15)0.0579 (16)0.0501 (15)0.0052 (13)−0.0090 (12)−0.0099 (12)
C130.0656 (18)0.0669 (19)0.0582 (16)0.0019 (15)−0.0125 (14)−0.0036 (15)
C140.080 (2)0.075 (2)0.082 (2)0.0162 (19)−0.033 (2)−0.0011 (19)
C150.077 (3)0.099 (3)0.099 (3)0.031 (2)−0.018 (2)−0.020 (2)
C160.066 (2)0.101 (3)0.081 (2)0.021 (2)0.0003 (18)−0.021 (2)
C170.0593 (18)0.0718 (19)0.0586 (17)0.0068 (14)−0.0012 (14)−0.0115 (16)
C180.071 (2)0.0627 (18)0.0471 (14)0.0018 (15)−0.0013 (14)−0.0036 (13)
C190.084 (2)0.077 (2)0.0655 (18)0.0096 (18)−0.0145 (18)0.0093 (17)
C200.129 (4)0.099 (3)0.111 (3)−0.020 (3)−0.046 (3)0.045 (3)
N10.0567 (14)0.0597 (13)0.0449 (11)0.0061 (11)−0.0005 (11)−0.0005 (10)
N20.0730 (17)0.0795 (17)0.0523 (13)0.0063 (15)0.0105 (14)−0.0061 (12)
O10.0643 (15)0.121 (2)0.106 (2)−0.0134 (15)−0.0203 (16)0.0323 (18)
OW0.124 (3)0.177 (3)0.0739 (17)0.012 (3)0.0232 (18)0.0031 (19)

Geometric parameters (Å, °)

Fe1—C5'1.98 (3)C7—C81.387 (5)
Fe1—C42.000 (10)C7—H70.9300
Fe1—C12.011 (12)C8—C91.416 (5)
Fe1—C72.029 (4)C8—H80.9300
Fe1—C102.029 (3)C9—C101.424 (4)
Fe1—C62.034 (3)C9—H90.9300
Fe1—C82.037 (4)C10—C111.494 (4)
Fe1—C92.038 (3)C11—N11.469 (4)
Fe1—C3'2.036 (17)C11—H11A0.9700
Fe1—C22.040 (10)C11—H11B0.9700
Fe1—C2'2.05 (2)C12—N11.383 (4)
Fe1—C32.048 (8)C12—C131.392 (4)
C1—C51.388 (12)C12—C171.404 (4)
C1—C21.451 (13)C13—C141.390 (5)
C1—H10.9300C13—H13A0.9300
C2—C31.444 (14)C14—C151.403 (6)
C2—H20.9300C14—H14A0.9300
C3—C41.423 (10)C15—C161.365 (6)
C3—H30.9300C15—H15A0.9300
C4—C51.46 (2)C16—C171.400 (5)
C4—H40.9300C16—H16A0.9300
C5—H50.9300C17—N21.393 (4)
C1'—C5'1.34 (2)C18—N21.325 (4)
C1'—C2'1.49 (3)C18—N11.370 (4)
C1'—H1'0.9300C18—C191.516 (5)
C2'—C3'1.33 (2)C19—O11.428 (5)
C2'—H2'0.9300C19—C201.507 (6)
C3'—C4'1.37 (2)C19—H19A0.9800
C3'—H3'0.9300C20—H20A0.9600
C4'—C5'1.40 (4)C20—H20B0.9600
C4'—H4'0.9300C20—H20C0.9600
C5'—H5'0.9300O1—H1''0.8200
C6—C101.415 (4)OW—HWB0.8501
C6—C71.421 (5)OW—HWC0.8500
C6—H60.9300
C5'—Fe1—C446.8 (9)Fe1—C1'—H1'125.5
C5'—Fe1—C127.6 (8)C3'—C2'—C1'108.2 (18)
C4—Fe1—C166.5 (5)C3'—C2'—Fe170.5 (12)
C5'—Fe1—C7165.0 (8)C1'—C2'—Fe170.4 (12)
C4—Fe1—C7119.8 (4)C3'—C2'—H2'125.9
C1—Fe1—C7165.2 (3)C1'—C2'—H2'125.9
C5'—Fe1—C10122.4 (9)Fe1—C2'—H2'124.8
C4—Fe1—C10164.4 (4)C2'—C3'—C4'117 (2)
C1—Fe1—C10108.7 (4)C2'—C3'—Fe171.4 (11)
C7—Fe1—C1068.85 (13)C4'—C3'—Fe173.6 (13)
C5'—Fe1—C6154.1 (8)C2'—C3'—H3'121.4
C4—Fe1—C6153.9 (4)C4'—C3'—H3'121.4
C1—Fe1—C6127.8 (4)Fe1—C3'—H3'125.2
C7—Fe1—C640.95 (14)C3'—C4'—C5'94.2 (18)
C10—Fe1—C640.76 (12)C3'—C4'—Fe167.7 (12)
C5'—Fe1—C8131.0 (7)C5'—C4'—Fe165.2 (16)
C4—Fe1—C8108.8 (4)C3'—C4'—H4'132.9
C1—Fe1—C8154.1 (3)C5'—C4'—H4'132.9
C7—Fe1—C839.88 (15)Fe1—C4'—H4'125.9
C10—Fe1—C868.68 (13)C1'—C5'—C4'125 (2)
C6—Fe1—C868.00 (15)C1'—C5'—Fe175.1 (16)
C5'—Fe1—C9112.9 (8)C4'—C5'—Fe174.9 (17)
C4—Fe1—C9127.2 (4)C1'—C5'—H5'117.5
C1—Fe1—C9120.3 (3)C4'—C5'—H5'117.5
C7—Fe1—C968.11 (16)Fe1—C5'—H5'124.1
C10—Fe1—C941.00 (11)C10—C6—C7107.9 (3)
C6—Fe1—C968.35 (13)C10—C6—Fe169.42 (17)
C8—Fe1—C940.68 (14)C7—C6—Fe169.3 (2)
C5'—Fe1—C3'60.7 (11)C10—C6—H6126.0
C4—Fe1—C3'22.4 (5)C7—C6—H6126.0
C1—Fe1—C3'71.2 (7)Fe1—C6—H6126.8
C7—Fe1—C3'109.4 (6)C8—C7—C6108.3 (3)
C10—Fe1—C3'172.7 (8)C8—C7—Fe170.4 (2)
C6—Fe1—C3'133.4 (7)C6—C7—Fe169.73 (19)
C8—Fe1—C3'114.8 (6)C8—C7—H7125.8
C9—Fe1—C3'145.6 (7)C6—C7—H7125.8
C5'—Fe1—C260.2 (7)Fe1—C7—H7125.6
C4—Fe1—C268.0 (4)C7—C8—C9108.7 (3)
C1—Fe1—C242.0 (3)C7—C8—Fe169.7 (2)
C7—Fe1—C2125.4 (3)C9—C8—Fe169.69 (19)
C10—Fe1—C2119.1 (4)C7—C8—H8125.7
C6—Fe1—C2106.9 (3)C9—C8—H8125.7
C8—Fe1—C2162.5 (4)Fe1—C8—H8126.5
C9—Fe1—C2154.8 (4)C8—C9—C10107.7 (3)
C3'—Fe1—C255.6 (6)C8—C9—Fe169.6 (2)
C5'—Fe1—C2'62.6 (10)C10—C9—Fe169.17 (17)
C4—Fe1—C2'54.3 (6)C8—C9—H9126.1
C1—Fe1—C2'53.3 (7)C10—C9—H9126.1
C7—Fe1—C2'117.7 (7)Fe1—C9—H9126.6
C10—Fe1—C2'135.9 (7)C6—C10—C9107.3 (3)
C6—Fe1—C2'113.2 (6)C6—C10—C11126.2 (3)
C8—Fe1—C2'146.1 (8)C9—C10—C11126.4 (3)
C9—Fe1—C2'173.2 (8)C6—C10—Fe169.82 (17)
C3'—Fe1—C2'38.1 (7)C9—C10—Fe169.83 (17)
C2—Fe1—C2'18.9 (6)C11—C10—Fe1127.10 (19)
C5'—Fe1—C369.0 (9)N1—C11—C10110.9 (2)
C4—Fe1—C341.1 (3)N1—C11—H11A109.5
C1—Fe1—C369.7 (5)C10—C11—H11A109.5
C7—Fe1—C3105.6 (3)N1—C11—H11B109.5
C10—Fe1—C3153.1 (4)C10—C11—H11B109.5
C6—Fe1—C3117.8 (4)H11A—C11—H11B108.1
C8—Fe1—C3124.8 (4)N1—C12—C13131.8 (3)
C9—Fe1—C3163.2 (4)N1—C12—C17105.7 (3)
C3'—Fe1—C319.7 (5)C13—C12—C17122.4 (3)
C2—Fe1—C341.4 (4)C14—C13—C12115.9 (3)
C2'—Fe1—C322.5 (5)C14—C13—H13A122.0
C5—C1—C2113.8 (11)C12—C13—H13A122.0
C5—C1—Fe172.1 (9)C13—C14—C15122.2 (4)
C2—C1—Fe170.1 (6)C13—C14—H14A118.9
C5—C1—H1123.1C15—C14—H14A118.9
C2—C1—H1123.1C16—C15—C14121.2 (4)
Fe1—C1—H1126.5C16—C15—H15A119.4
C3—C2—C1106.5 (8)C14—C15—H15A119.4
C3—C2—Fe169.6 (5)C15—C16—C17118.2 (4)
C1—C2—Fe168.0 (6)C15—C16—H16A120.9
C3—C2—H2126.8C17—C16—H16A120.9
C1—C2—H2126.8N2—C17—C16130.1 (3)
Fe1—C2—H2127.2N2—C17—C12109.8 (3)
C4—C3—C2103.9 (8)C16—C17—C12120.1 (3)
C4—C3—Fe167.6 (5)N2—C18—N1113.2 (3)
C2—C3—Fe169.0 (5)N2—C18—C19124.8 (3)
C4—C3—H3128.0N1—C18—C19121.9 (3)
C2—C3—H3128.0O1—C19—C20111.6 (3)
Fe1—C3—H3126.9O1—C19—C18108.6 (3)
C3—C4—C5114.6 (10)C20—C19—C18112.2 (4)
C3—C4—Fe171.2 (5)O1—C19—H19A108.1
C5—C4—Fe171.3 (8)C20—C19—H19A108.1
C3—C4—H4122.7C18—C19—H19A108.1
C5—C4—H4122.7C19—C20—H20A109.5
Fe1—C4—H4126.5C19—C20—H20B109.5
C1—C5—C4101.1 (10)H20A—C20—H20B109.5
C1—C5—Fe168.1 (8)C19—C20—H20C109.5
C4—C5—Fe166.7 (8)H20A—C20—H20C109.5
C1—C5—H5129.4H20B—C20—H20C109.5
C4—C5—H5129.4C18—N1—C12106.5 (2)
Fe1—C5—H5127.2C18—N1—C11128.8 (3)
C5'—C1'—C2'95 (2)C12—N1—C11124.6 (2)
C5'—C1'—Fe166.6 (17)C18—N2—C17104.7 (3)
C2'—C1'—Fe167.4 (12)C19—O1—H1''109.5
C5'—C1'—H1'132.3HWB—OW—HWC109.5
C2'—C1'—H1'132.3

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
OW—HWB···O1i0.852.372.806 (5)112
O1—H1''···OW0.822.343.016 (5)140

Symmetry codes: (i) x+1/2, −y+1/2, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2334).

References

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