Download citation
Download citation
link to html
In a search for potent fungicidal agents, the title compound, [Fe(C5H5)(C17H18N3O)], has been synthesized and its single-crystal structure determined. It has proven that a bulky group, such as ferrocene, close to the triazole ring results in a decreased fungicidal activity.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804025620/kp6004sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804025620/kp6004Isup2.hkl
Contains datablock I

CCDC reference: 225121

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.042
  • wR factor = 0.108
  • Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT165_ALERT_3_C Nr. of Status R Flagged Non-Hydrogen Atoms ..... 10 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.63 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.24 Ratio PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors for C7' PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors for C10' PLAT301_ALERT_3_C Main Residue Disorder ......................... 16.00 Perc. PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 4 C9 -FE1 -C1 -C2 -157.00 5.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 14 C9 -FE1 -C1 -C5 84.00 5.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 24 C9 -FE1 -C1 -C11 -36.00 5.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 45 C10 -FE1 -C2 -C3 155.00 3.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 55 C10 -FE1 -C2 -C1 35.00 3.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 94 C7 -FE1 -C4 -C3 -37.00 15.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 104 C7 -FE1 -C4 -C5 83.00 15.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 116 C8 -FE1 -C5 -C4 126.00 14.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 126 C8 -FE1 -C5 -C1 -115.00 14.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 140 C3 -FE1 -C6 -C7 67.00 4.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 150 C3 -FE1 -C6 -C10 -174.00 4.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 163 C4 -FE1 -C7 -C6 -139.00 15.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 173 C4 -FE1 -C7 -C8 102.00 15.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 184 C5 -FE1 -C8 -C9 -60.00 15.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 195 C5 -FE1 -C8 -C7 58.00 15.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 212 C1 -FE1 -C9 -C10 -20.00 5.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 222 C1 -FE1 -C9 -C8 98.00 5.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 239 C2 -FE1 -C10 -C9 146.00 3.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 250 C2 -FE1 -C10 -C6 27.00 3.00 1.555 1.555 1.555 1.555
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 26.46 From the CIF: _reflns_number_total 3690 Count of symmetry unique reflns 2071 Completeness (_total/calc) 178.17% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1619 Fraction of Friedel pairs measured 0.782 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 26 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 20 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

1-(1-Ferrocenyl-1-methoxy-3-phenylpropan-2-yl)-1H-1,2,4-triazole top
Crystal data top
[Fe(C5H5)(C17H18N3O)]F(000) = 840
Mr = 401.28Dx = 1.392 Mg m3
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P2c-2acCell parameters from 840 reflections
a = 10.165 (5) Åθ = 2.5–22.4°
b = 14.205 (7) ŵ = 0.80 mm1
c = 13.262 (6) ÅT = 293 K
V = 1915.0 (16) Å3Prism, yellow
Z = 40.32 × 0.25 × 0.20 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
3690 independent reflections
Radiation source: fine-focus sealed tube2665 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.049
φ and ω scansθmax = 26.5°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1212
Tmin = 0.715, Tmax = 0.851k = 1217
10319 measured reflectionsl = 1613
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.042 w = 1/[σ2(Fo2) + (0.0506P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.108(Δ/σ)max < 0.001
S = 1.06Δρmax = 0.24 e Å3
3690 reflectionsΔρmin = 0.20 e Å3
247 parametersExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.0036 (6)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983)
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.02 (3)
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)
Fe10.05309 (5)0.61332 (4)0.80591 (6)0.03933 (17)
N10.0026 (3)0.8984 (2)1.0992 (2)0.0368 (7)
N20.0936 (4)0.9498 (3)1.0553 (3)0.0506 (10)
N30.0272 (5)1.0409 (3)1.1561 (3)0.0656 (12)
O10.1646 (3)0.8160 (2)0.9464 (2)0.0565 (8)
C10.0281 (4)0.6793 (3)0.9414 (3)0.0375 (11)
C20.1308 (5)0.6119 (3)0.9485 (3)0.0437 (11)
H20.21750.62450.96660.052*
C30.0793 (5)0.5228 (4)0.9236 (4)0.0521 (13)
H30.12630.46660.92180.062*
C40.0546 (5)0.5333 (3)0.9021 (4)0.0495 (12)
H40.11220.48530.88380.059*
C50.0874 (5)0.6297 (3)0.9130 (4)0.0426 (11)
H50.17030.65600.90320.051*
C60.0323 (11)0.7121 (4)0.6937 (4)0.064 (4)0.64 (2)
H60.01000.76990.69900.077*0.64 (2)
C70.1658 (9)0.6951 (9)0.7120 (4)0.063 (3)0.64 (2)
H70.22770.73970.73160.075*0.64 (2)
C80.1897 (8)0.5994 (10)0.6956 (4)0.060 (3)0.64 (2)
H80.27030.56910.70240.072*0.64 (2)
C90.0710 (14)0.5572 (4)0.6672 (4)0.066 (3)0.64 (2)
H90.05890.49390.65180.080*0.64 (2)
C100.0262 (6)0.6268 (7)0.6660 (4)0.062 (4)0.64 (2)
H100.11430.61800.64960.074*0.64 (2)
C6'0.0693 (10)0.7106 (4)0.6956 (4)0.051 (6)0.36 (2)
H6'0.06260.77540.70450.062*0.36 (2)
C7'0.1863 (5)0.6562 (10)0.7047 (4)0.065 (6)0.36 (2)
H7'0.26950.67910.72050.078*0.36 (2)
C8'0.1536 (13)0.5603 (8)0.6854 (4)0.043 (4)0.36 (2)
H8'0.21170.50980.68630.052*0.36 (2)
C9'0.0164 (14)0.5556 (5)0.6644 (4)0.047 (5)0.36 (2)
H9'0.03090.50140.64920.056*0.36 (2)
C10'0.0357 (6)0.6485 (8)0.6707 (4)0.062 (7)0.36 (2)
H10'0.12300.66560.66040.074*0.36 (2)
C110.0374 (4)0.7819 (3)0.9679 (3)0.0389 (10)
H110.02750.81740.92870.047*
C120.0133 (4)0.7980 (3)1.0805 (3)0.0373 (9)
H120.09190.77601.11620.045*
C130.1040 (4)0.7463 (3)1.1263 (3)0.0458 (11)
H13A0.18430.76721.09370.055*
H13B0.09480.67921.11470.055*
C140.1129 (4)0.7650 (3)1.2377 (3)0.0396 (10)
C150.0334 (4)0.7181 (3)1.3045 (5)0.0587 (11)
H150.02150.67021.28160.070*
C160.0346 (6)0.7418 (5)1.4057 (4)0.0787 (18)
H160.02150.71091.45020.094*
C170.1151 (7)0.8083 (5)1.4400 (5)0.085 (2)
H170.11470.82351.50820.102*
C180.1980 (7)0.8543 (4)1.3764 (5)0.076 (2)
H180.25480.90021.40100.092*
C190.1971 (5)0.8322 (3)1.2743 (3)0.0532 (14)
H190.25390.86331.23050.064*
C200.0710 (5)0.9553 (4)1.1584 (4)0.0568 (13)
H200.14230.93601.19710.068*
C210.0732 (5)1.0339 (3)1.0920 (4)0.0547 (12)
H210.12511.08531.07450.066*
C220.1710 (7)0.8947 (5)0.8841 (5)0.098 (2)
H22A0.12640.88160.82180.146*
H22B0.26140.90970.87050.146*
H22C0.12960.94720.91690.146*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0481 (3)0.0383 (3)0.0315 (2)0.0011 (3)0.0045 (4)0.0012 (4)
N10.0404 (17)0.040 (2)0.0302 (17)0.0034 (16)0.0018 (14)0.0024 (16)
N20.054 (2)0.040 (2)0.058 (2)0.0012 (18)0.0125 (18)0.006 (2)
N30.085 (3)0.043 (3)0.069 (3)0.009 (2)0.012 (2)0.018 (2)
O10.0612 (19)0.054 (2)0.0542 (19)0.0144 (16)0.0148 (15)0.0048 (17)
C10.046 (3)0.041 (3)0.025 (2)0.003 (2)0.0054 (19)0.001 (2)
C20.049 (3)0.049 (3)0.034 (2)0.009 (2)0.001 (2)0.002 (2)
C30.075 (4)0.036 (3)0.045 (3)0.014 (2)0.008 (3)0.007 (2)
C40.061 (3)0.039 (3)0.048 (3)0.010 (2)0.015 (2)0.003 (2)
C50.045 (3)0.045 (3)0.038 (2)0.003 (2)0.008 (2)0.005 (2)
C60.077 (6)0.064 (7)0.052 (6)0.003 (5)0.001 (4)0.013 (5)
C70.084 (6)0.052 (6)0.051 (5)0.013 (5)0.030 (5)0.001 (4)
C80.067 (5)0.063 (8)0.051 (5)0.001 (5)0.022 (4)0.009 (5)
C90.088 (8)0.066 (6)0.045 (5)0.005 (5)0.005 (5)0.018 (5)
C100.076 (7)0.072 (6)0.037 (5)0.005 (5)0.018 (5)0.006 (5)
C6'0.062 (9)0.051 (9)0.041 (8)0.001 (7)0.000 (6)0.014 (7)
C7'0.074 (9)0.063 (10)0.058 (8)0.015 (7)0.016 (7)0.002 (8)
C8'0.047 (8)0.045 (7)0.037 (7)0.002 (7)0.014 (6)0.015 (6)
C9'0.048 (8)0.065 (9)0.027 (7)0.000 (7)0.000 (5)0.010 (6)
C10'0.074 (11)0.062 (9)0.049 (10)0.014 (8)0.001 (8)0.004 (7)
C110.046 (3)0.036 (2)0.035 (2)0.003 (2)0.0018 (19)0.0003 (18)
C120.046 (2)0.033 (2)0.033 (2)0.0002 (18)0.0005 (18)0.0017 (18)
C130.052 (3)0.044 (3)0.042 (2)0.006 (2)0.002 (2)0.003 (2)
C140.046 (2)0.035 (2)0.038 (2)0.005 (2)0.010 (2)0.0001 (19)
C150.063 (3)0.068 (3)0.045 (2)0.010 (2)0.007 (3)0.009 (4)
C160.083 (4)0.114 (5)0.039 (3)0.030 (4)0.008 (3)0.011 (3)
C170.110 (5)0.096 (5)0.051 (3)0.056 (5)0.035 (4)0.029 (4)
C180.089 (5)0.050 (3)0.090 (5)0.014 (3)0.052 (4)0.019 (3)
C190.053 (3)0.040 (3)0.066 (4)0.003 (2)0.018 (2)0.002 (2)
C200.060 (3)0.061 (3)0.050 (3)0.012 (3)0.013 (2)0.010 (2)
C210.064 (3)0.041 (3)0.060 (3)0.003 (2)0.004 (3)0.003 (2)
C220.139 (6)0.082 (4)0.072 (4)0.049 (4)0.008 (4)0.025 (4)
Geometric parameters (Å, º) top
Fe1—C7'2.002 (4)C9—C101.399 (3)
Fe1—C92.014 (5)C9—H90.9300
Fe1—C6'2.019 (5)C10—H100.9300
Fe1—C82.026 (4)C6'—C10'1.424 (4)
Fe1—C52.027 (5)C6'—C7'1.424 (4)
Fe1—C42.030 (4)C6'—H6'0.9300
Fe1—C102.032 (5)C7'—C8'1.424 (4)
Fe1—C32.040 (5)C7'—H7'0.9300
Fe1—C8'2.041 (5)C8'—C9'1.424 (4)
Fe1—C12.043 (4)C8'—H8'0.9300
Fe1—C22.050 (4)C9'—C10'1.424 (4)
Fe1—C72.052 (5)C9'—H9'0.9300
N1—C201.324 (5)C10'—H10'0.9300
N1—N21.351 (5)C11—C121.531 (5)
N1—C121.453 (5)C11—H110.9800
N2—C211.306 (6)C12—C131.526 (6)
N3—C201.295 (6)C12—H120.9800
N3—C211.332 (6)C13—C141.505 (6)
O1—C221.392 (6)C13—H13A0.9700
O1—C111.410 (5)C13—H13B0.9700
C1—C21.420 (6)C14—C151.371 (6)
C1—C51.421 (6)C14—C191.371 (6)
C1—C111.501 (6)C15—C161.385 (8)
C2—C31.410 (7)C15—H150.9300
C2—H20.9300C16—C171.330 (9)
C3—C41.399 (6)C16—H160.9300
C3—H30.9300C17—C181.360 (9)
C4—C51.417 (6)C17—H170.9300
C4—H40.9300C18—C191.390 (8)
C5—H50.9300C18—H180.9300
C6—C71.399 (4)C19—H190.9300
C6—C101.399 (4)C20—H200.9300
C6—H60.9300C21—H210.9300
C7—C81.399 (4)C22—H22A0.9600
C7—H70.9300C22—H22B0.9600
C8—C91.399 (4)C22—H22C0.9600
C8—H80.9300
C7'—Fe1—C956.40 (15)C7—C6—H6126.0
C7'—Fe1—C6'41.49 (11)C10—C6—H6126.0
C9—Fe1—C6'66.55 (17)Fe1—C6—H6126.5
C7'—Fe1—C823.38 (7)C6—C7—C8108.0
C9—Fe1—C840.51 (11)C6—C7—Fe170.24 (18)
C6'—Fe1—C859.22 (15)C8—C7—Fe168.94 (19)
C7'—Fe1—C5155.7 (4)C6—C7—H7126.0
C9—Fe1—C5138.5 (4)C8—C7—H7126.0
C6'—Fe1—C5119.1 (3)Fe1—C7—H7126.4
C8—Fe1—C5178.1 (2)C9—C8—C7108.0
C7'—Fe1—C4163.1 (4)C9—C8—Fe169.26 (19)
C9—Fe1—C4113.6 (3)C7—C8—Fe170.96 (19)
C6'—Fe1—C4152.0 (3)C9—C8—H8126.0
C8—Fe1—C4140.2 (4)C7—C8—H8126.0
C5—Fe1—C440.90 (18)Fe1—C8—H8125.4
C7'—Fe1—C1068.12 (17)C10—C9—C8108.0
C9—Fe1—C1040.44 (11)C10—C9—Fe170.49 (18)
C6'—Fe1—C1046.08 (12)C8—C9—Fe170.23 (18)
C8—Fe1—C1067.78 (17)C10—C9—H9126.0
C5—Fe1—C10110.4 (3)C8—C9—H9126.0
C4—Fe1—C10114.4 (2)Fe1—C9—H9124.9
C7'—Fe1—C3128.0 (3)C9—C10—C6108.0
C9—Fe1—C3115.9 (2)C9—C10—Fe169.06 (19)
C6'—Fe1—C3167.2 (3)C6—C10—Fe170.91 (19)
C8—Fe1—C3113.6 (3)C9—C10—H10126.0
C5—Fe1—C368.2 (2)C6—C10—H10126.0
C4—Fe1—C340.22 (18)Fe1—C10—H10125.6
C10—Fe1—C3144.1 (3)C10'—C6'—C7'108.0
C7'—Fe1—C8'41.25 (11)C10'—C6'—Fe171.50 (19)
C9—Fe1—C8'24.91 (7)C7'—C6'—Fe168.59 (18)
C6'—Fe1—C8'69.17 (17)C10'—C6'—H6'126.0
C8—Fe1—C8'19.19 (5)C7'—C6'—H6'126.0
C5—Fe1—C8'160.7 (5)Fe1—C6'—H6'125.5
C4—Fe1—C8'123.8 (4)C6'—C7'—C8'108.0
C10—Fe1—C8'61.20 (16)C6'—C7'—Fe169.92 (19)
C3—Fe1—C8'107.5 (2)C8'—C7'—Fe170.9 (2)
C7'—Fe1—C1122.3 (4)C6'—C7'—H7'126.0
C9—Fe1—C1175.5 (3)C8'—C7'—H7'126.0
C6'—Fe1—C1109.5 (2)Fe1—C7'—H7'124.8
C8—Fe1—C1139.9 (4)C9'—C8'—C7'108.0
C5—Fe1—C140.85 (18)C9'—C8'—Fe171.35 (18)
C4—Fe1—C168.73 (19)C7'—C8'—Fe167.89 (19)
C10—Fe1—C1135.3 (3)C9'—C8'—H8'126.0
C3—Fe1—C168.4 (2)C7'—C8'—H8'126.0
C8'—Fe1—C1157.0 (5)Fe1—C8'—H8'126.3
C7'—Fe1—C2111.1 (2)C8'—C9'—C10'108.0
C9—Fe1—C2143.5 (3)C8'—C9'—Fe168.25 (17)
C6'—Fe1—C2130.1 (3)C10'—C9'—Fe169.43 (18)
C8—Fe1—C2113.6 (3)C8'—C9'—H9'126.0
C5—Fe1—C268.07 (19)C10'—C9'—H9'126.0
C4—Fe1—C267.8 (2)Fe1—C9'—H9'127.9
C10—Fe1—C2175.1 (3)C6'—C10'—C9'108.0
C3—Fe1—C240.32 (19)C6'—C10'—Fe167.74 (19)
C8'—Fe1—C2121.7 (3)C9'—C10'—Fe170.43 (19)
C1—Fe1—C240.61 (17)C6'—C10'—H10'126.0
C7'—Fe1—C716.9C9'—C10'—H10'126.0
C9—Fe1—C767.63 (17)Fe1—C10'—H10'127.4
C6'—Fe1—C729.24 (8)O1—C11—C1110.1 (3)
C8—Fe1—C740.10 (11)O1—C11—C12107.0 (3)
C5—Fe1—C7138.9 (4)C1—C11—C12111.3 (3)
C4—Fe1—C7178.3 (2)O1—C11—H11109.4
C10—Fe1—C767.28 (17)C1—C11—H11109.4
C3—Fe1—C7138.4 (3)C12—C11—H11109.4
C8'—Fe1—C756.91 (15)N1—C12—C13110.2 (3)
C1—Fe1—C7110.1 (3)N1—C12—C11109.0 (3)
C2—Fe1—C7110.5 (2)C13—C12—C11116.2 (4)
C20—N1—N2107.8 (4)N1—C12—H12107.0
C20—N1—C12131.4 (4)C13—C12—H12107.0
N2—N1—C12120.8 (3)C11—C12—H12107.0
C21—N2—N1102.7 (4)C14—C13—C12110.7 (4)
C20—N3—C21102.1 (4)C14—C13—H13A109.5
C22—O1—C11116.0 (4)C12—C13—H13A109.5
C2—C1—C5106.9 (4)C14—C13—H13B109.5
C2—C1—C11126.3 (4)C12—C13—H13B109.5
C5—C1—C11126.6 (4)H13A—C13—H13B108.1
C2—C1—Fe170.0 (2)C15—C14—C19118.6 (4)
C5—C1—Fe169.0 (3)C15—C14—C13120.9 (4)
C11—C1—Fe1130.0 (3)C19—C14—C13120.5 (4)
C3—C2—C1108.5 (4)C14—C15—C16120.2 (5)
C3—C2—Fe169.5 (3)C14—C15—H15119.9
C1—C2—Fe169.4 (3)C16—C15—H15119.9
C3—C2—H2125.8C17—C16—C15120.6 (6)
C1—C2—H2125.8C17—C16—H16119.7
Fe1—C2—H2126.9C15—C16—H16119.7
C4—C3—C2108.3 (4)C16—C17—C18120.7 (6)
C4—C3—Fe169.5 (3)C16—C17—H17119.6
C2—C3—Fe170.2 (3)C18—C17—H17119.6
C4—C3—H3125.9C17—C18—C19119.5 (6)
C2—C3—H3125.9C17—C18—H18120.3
Fe1—C3—H3126.0C19—C18—H18120.3
C3—C4—C5108.1 (4)C14—C19—C18120.4 (5)
C3—C4—Fe170.3 (3)C14—C19—H19119.8
C5—C4—Fe169.5 (3)C18—C19—H19119.8
C3—C4—H4125.9N3—C20—N1112.2 (4)
C5—C4—H4125.9N3—C20—H20123.9
Fe1—C4—H4125.9N1—C20—H20123.9
C4—C5—C1108.2 (4)N2—C21—N3115.2 (4)
C4—C5—Fe169.6 (3)N2—C21—H21122.4
C1—C5—Fe170.2 (3)N3—C21—H21122.4
C4—C5—H5125.9O1—C22—H22A109.5
C1—C5—H5125.9O1—C22—H22B109.5
Fe1—C5—H5125.9H22A—C22—H22B109.5
C7—C6—C10108.0O1—C22—H22C109.5
C7—C6—Fe169.96 (18)H22A—C22—H22C109.5
C10—C6—Fe169.08 (19)H22B—C22—H22C109.5
C20—N1—N2—C210.5 (5)C7'—Fe1—C9—C1095.16 (13)
C12—N1—N2—C21178.2 (4)C6'—Fe1—C9—C1048.96 (9)
C7'—Fe1—C1—C285.3 (4)C8—Fe1—C9—C10118.40 (12)
C9—Fe1—C1—C2157 (5)C5—Fe1—C9—C1059.1 (5)
C6'—Fe1—C1—C2129.5 (4)C4—Fe1—C9—C10100.4 (4)
C8—Fe1—C1—C264.6 (5)C3—Fe1—C9—C10144.9 (4)
C5—Fe1—C1—C2118.2 (4)C8'—Fe1—C9—C10139.73 (10)
C4—Fe1—C1—C280.3 (3)C1—Fe1—C9—C1020 (5)
C10—Fe1—C1—C2176.0 (4)C2—Fe1—C9—C10175.3 (4)
C3—Fe1—C1—C237.0 (3)C7—Fe1—C9—C1080.74 (13)
C8'—Fe1—C1—C247.2 (8)C7'—Fe1—C9—C823.2
C7—Fe1—C1—C298.4 (4)C6'—Fe1—C9—C869.45 (12)
C7'—Fe1—C1—C5156.5 (4)C5—Fe1—C9—C8177.5 (5)
C9—Fe1—C1—C584 (5)C4—Fe1—C9—C8141.2 (4)
C6'—Fe1—C1—C5112.3 (4)C10—Fe1—C9—C8118.40 (12)
C8—Fe1—C1—C5177.3 (4)C3—Fe1—C9—C896.7 (4)
C4—Fe1—C1—C537.8 (3)C8'—Fe1—C9—C821.3
C10—Fe1—C1—C565.8 (5)C1—Fe1—C9—C898 (5)
C3—Fe1—C1—C581.2 (3)C2—Fe1—C9—C856.9 (4)
C8'—Fe1—C1—C5165.3 (6)C7—Fe1—C9—C837.66 (8)
C2—Fe1—C1—C5118.2 (4)C8—C9—C10—C60.0
C7—Fe1—C1—C5143.4 (5)Fe1—C9—C10—C660.5 (2)
C7'—Fe1—C1—C1135.8 (5)C8—C9—C10—Fe160.50 (19)
C9—Fe1—C1—C1136 (5)C7—C6—C10—C90.0
C6'—Fe1—C1—C118.4 (5)Fe1—C6—C10—C959.34 (18)
C8—Fe1—C1—C1156.5 (6)C7—C6—C10—Fe159.34 (18)
C5—Fe1—C1—C11120.7 (5)C7'—Fe1—C10—C963.36 (12)
C4—Fe1—C1—C11158.6 (4)C6'—Fe1—C10—C9106.15 (12)
C10—Fe1—C1—C1154.9 (5)C8—Fe1—C10—C938.11 (9)
C3—Fe1—C1—C11158.1 (5)C5—Fe1—C10—C9142.7 (5)
C8'—Fe1—C1—C1173.9 (8)C4—Fe1—C10—C998.5 (5)
C2—Fe1—C1—C11121.1 (5)C3—Fe1—C10—C961.9 (5)
C7—Fe1—C1—C1122.7 (5)C8'—Fe1—C10—C918.1
C5—C1—C2—C30.7 (5)C1—Fe1—C10—C9177.8 (5)
C11—C1—C2—C3175.8 (4)C2—Fe1—C10—C9146 (3)
Fe1—C1—C2—C358.7 (3)C7—Fe1—C10—C981.67 (13)
C5—C1—C2—Fe159.3 (3)C7'—Fe1—C10—C655.48 (11)
C11—C1—C2—Fe1125.6 (4)C9—Fe1—C10—C6118.85 (11)
C7'—Fe1—C2—C3124.4 (5)C6'—Fe1—C10—C612.7
C9—Fe1—C2—C362.8 (6)C8—Fe1—C10—C680.74 (13)
C6'—Fe1—C2—C3168.0 (4)C5—Fe1—C10—C698.5 (5)
C8—Fe1—C2—C399.3 (5)C4—Fe1—C10—C6142.7 (4)
C5—Fe1—C2—C381.7 (3)C3—Fe1—C10—C6179.2 (5)
C4—Fe1—C2—C337.4 (3)C8'—Fe1—C10—C6100.75 (13)
C10—Fe1—C2—C3155 (3)C1—Fe1—C10—C658.9 (5)
C8'—Fe1—C2—C379.6 (6)C2—Fe1—C10—C627 (3)
C1—Fe1—C2—C3120.1 (4)C7—Fe1—C10—C637.18 (9)
C7—Fe1—C2—C3142.6 (5)C7'—Fe1—C6'—C10'118.77 (12)
C7'—Fe1—C2—C1115.4 (5)C9—Fe1—C6'—C10'53.61 (10)
C9—Fe1—C2—C1177.1 (5)C8—Fe1—C6'—C10'98.68 (14)
C6'—Fe1—C2—C171.8 (5)C5—Fe1—C6'—C10'80.3 (5)
C8—Fe1—C2—C1140.6 (5)C4—Fe1—C6'—C10'43.0 (7)
C5—Fe1—C2—C138.4 (3)C10—Fe1—C6'—C10'10.8
C4—Fe1—C2—C182.7 (3)C3—Fe1—C6'—C10'157.7 (11)
C10—Fe1—C2—C135 (3)C8'—Fe1—C6'—C10'80.40 (14)
C3—Fe1—C2—C1120.1 (4)C1—Fe1—C6'—C10'124.1 (4)
C8'—Fe1—C2—C1160.3 (5)C2—Fe1—C6'—C10'165.1 (4)
C7—Fe1—C2—C197.3 (5)C7—Fe1—C6'—C10'139.33 (10)
C1—C2—C3—C40.6 (5)C9—Fe1—C6'—C7'65.15 (11)
Fe1—C2—C3—C459.2 (3)C8—Fe1—C6'—C7'20.1
C1—C2—C3—Fe158.6 (3)C5—Fe1—C6'—C7'161.0 (5)
C7'—Fe1—C3—C4163.0 (5)C4—Fe1—C6'—C7'161.8 (7)
C9—Fe1—C3—C496.6 (5)C10—Fe1—C6'—C7'107.93 (12)
C6'—Fe1—C3—C4165.1 (11)C3—Fe1—C6'—C7'38.9 (11)
C8—Fe1—C3—C4141.4 (5)C8'—Fe1—C6'—C7'38.37 (8)
C5—Fe1—C3—C438.0 (3)C1—Fe1—C6'—C7'117.2 (5)
C10—Fe1—C3—C457.1 (6)C2—Fe1—C6'—C7'76.2 (4)
C8'—Fe1—C3—C4121.9 (6)C7—Fe1—C6'—C7'20.6
C1—Fe1—C3—C482.1 (3)C10'—C6'—C7'—C8'0.0
C2—Fe1—C3—C4119.4 (4)Fe1—C6'—C7'—C8'60.9 (2)
C7—Fe1—C3—C4178.5 (5)C10'—C6'—C7'—Fe160.9 (2)
C7'—Fe1—C3—C277.6 (6)C9—Fe1—C7'—C6'91.73 (12)
C9—Fe1—C3—C2144.0 (5)C8—Fe1—C7'—C6'131.97 (9)
C6'—Fe1—C3—C245.7 (12)C5—Fe1—C7'—C6'43.8 (7)
C8—Fe1—C3—C299.2 (5)C4—Fe1—C7'—C6'149.6 (8)
C5—Fe1—C3—C281.4 (3)C10—Fe1—C7'—C6'47.61 (9)
C4—Fe1—C3—C2119.4 (4)C3—Fe1—C7'—C6'169.8 (3)
C10—Fe1—C3—C2176.5 (5)C8'—Fe1—C7'—C6'118.37 (11)
C8'—Fe1—C3—C2118.7 (6)C1—Fe1—C7'—C6'83.1 (4)
C1—Fe1—C3—C237.2 (3)C2—Fe1—C7'—C6'127.2 (3)
C7—Fe1—C3—C259.1 (6)C7—Fe1—C7'—C6'36.08 (6)
C2—C3—C4—C50.3 (6)C9—Fe1—C7'—C8'26.64 (5)
Fe1—C3—C4—C559.4 (3)C6'—Fe1—C7'—C8'118.37 (11)
C2—C3—C4—Fe159.7 (3)C8—Fe1—C7'—C8'13.6
C7'—Fe1—C4—C352.4 (9)C5—Fe1—C7'—C8'162.2 (7)
C9—Fe1—C4—C3102.8 (5)C4—Fe1—C7'—C8'31.3 (8)
C6'—Fe1—C4—C3173.0 (5)C10—Fe1—C7'—C8'70.76 (13)
C8—Fe1—C4—C363.3 (6)C3—Fe1—C7'—C8'71.8 (4)
C5—Fe1—C4—C3119.1 (4)C1—Fe1—C7'—C8'158.5 (4)
C10—Fe1—C4—C3147.3 (4)C2—Fe1—C7'—C8'114.5 (4)
C8'—Fe1—C4—C376.8 (5)C7—Fe1—C7'—C8'154.45 (7)
C1—Fe1—C4—C381.4 (3)C6'—C7'—C8'—C9'0.0
C2—Fe1—C4—C337.5 (3)Fe1—C7'—C8'—C9'60.34 (19)
C7—Fe1—C4—C337 (15)C6'—C7'—C8'—Fe160.33 (19)
C7'—Fe1—C4—C5171.6 (8)C7'—Fe1—C8'—C9'119.28 (11)
C9—Fe1—C4—C5138.0 (4)C9—Fe1—C8'—C9'1.7
C6'—Fe1—C4—C553.9 (6)C6'—Fe1—C8'—C9'80.69 (13)
C8—Fe1—C4—C5177.6 (5)C8—Fe1—C8'—C9'135.78 (9)
C10—Fe1—C4—C593.6 (4)C5—Fe1—C8'—C9'38.4 (7)
C3—Fe1—C4—C5119.1 (4)C4—Fe1—C8'—C9'71.2 (3)
C8'—Fe1—C4—C5164.1 (5)C10—Fe1—C8'—C9'30.31 (7)
C1—Fe1—C4—C537.8 (3)C3—Fe1—C8'—C9'112.4 (4)
C2—Fe1—C4—C581.6 (3)C1—Fe1—C8'—C9'171.6 (6)
C7—Fe1—C4—C583 (15)C2—Fe1—C8'—C9'154.3 (3)
C3—C4—C5—C10.1 (5)C7—Fe1—C8'—C9'110.65 (12)
Fe1—C4—C5—C159.8 (3)C9—Fe1—C8'—C7'117.56 (10)
C3—C4—C5—Fe159.9 (3)C6'—Fe1—C8'—C7'38.59 (9)
C2—C1—C5—C40.5 (5)C8—Fe1—C8'—C7'16.5
C11—C1—C5—C4175.6 (4)C5—Fe1—C8'—C7'157.7 (7)
Fe1—C1—C5—C459.5 (3)C4—Fe1—C8'—C7'169.5 (3)
C2—C1—C5—Fe160.0 (3)C10—Fe1—C8'—C7'88.97 (13)
C11—C1—C5—Fe1125.0 (4)C3—Fe1—C8'—C7'128.3 (4)
C7'—Fe1—C5—C4174.1 (5)C1—Fe1—C8'—C7'52.3 (5)
C9—Fe1—C5—C467.6 (4)C2—Fe1—C8'—C7'86.5 (3)
C6'—Fe1—C5—C4154.3 (4)C7—Fe1—C8'—C7'8.6
C8—Fe1—C5—C4126 (14)C7'—C8'—C9'—C10'0.0
C10—Fe1—C5—C4104.0 (4)Fe1—C8'—C9'—C10'58.17 (19)
C3—Fe1—C5—C437.4 (3)C7'—C8'—C9'—Fe158.18 (19)
C8'—Fe1—C5—C443.4 (8)C7'—Fe1—C9'—C8'38.12 (9)
C1—Fe1—C5—C4119.2 (4)C9—Fe1—C9'—C8'2.7
C2—Fe1—C5—C481.0 (3)C6'—Fe1—C9'—C8'82.87 (13)
C7—Fe1—C5—C4177.5 (4)C8—Fe1—C9'—C8'16.2
C7'—Fe1—C5—C154.8 (7)C5—Fe1—C9'—C8'165.7 (4)
C9—Fe1—C5—C1173.2 (3)C4—Fe1—C9'—C8'125.7 (4)
C6'—Fe1—C5—C186.5 (4)C10—Fe1—C9'—C8'120.82 (11)
C8—Fe1—C5—C1115 (14)C3—Fe1—C9'—C8'84.7 (4)
C4—Fe1—C5—C1119.2 (4)C1—Fe1—C9'—C8'169.3 (8)
C10—Fe1—C5—C1136.8 (4)C2—Fe1—C9'—C8'56.7 (5)
C3—Fe1—C5—C181.8 (3)C7—Fe1—C9'—C8'53.56 (12)
C8'—Fe1—C5—C1162.6 (6)C7'—Fe1—C9'—C10'82.22 (14)
C2—Fe1—C5—C138.2 (3)C9—Fe1—C9'—C10'117.62 (9)
C7—Fe1—C5—C158.3 (5)C6'—Fe1—C9'—C10'37.47 (9)
C7'—Fe1—C6—C717.4C8—Fe1—C9'—C10'104.18 (13)
C9—Fe1—C6—C781.51 (13)C5—Fe1—C9'—C10'73.9 (4)
C6'—Fe1—C6—C70.8C4—Fe1—C9'—C10'114.0 (4)
C8—Fe1—C6—C737.48 (8)C10—Fe1—C9'—C10'0.5
C5—Fe1—C6—C7143.3 (5)C3—Fe1—C9'—C10'154.9 (3)
C4—Fe1—C6—C7178.2 (5)C8'—Fe1—C9'—C10'120.34 (12)
C10—Fe1—C6—C7119.45 (11)C1—Fe1—C9'—C10'49.0 (8)
C3—Fe1—C6—C767 (4)C2—Fe1—C9'—C10'177.0 (5)
C8'—Fe1—C6—C756.24 (12)C7—Fe1—C9'—C10'66.78 (14)
C1—Fe1—C6—C799.9 (4)C7'—C6'—C10'—C9'0.0
C2—Fe1—C6—C763.7 (4)Fe1—C6'—C10'—C9'59.11 (19)
C7'—Fe1—C6—C10102.05 (13)C7'—C6'—C10'—Fe159.11 (19)
C9—Fe1—C6—C1037.93 (9)C8'—C9'—C10'—C6'0.0
C6'—Fe1—C6—C10120.27 (9)Fe1—C9'—C10'—C6'57.44 (18)
C8—Fe1—C6—C1081.97 (14)C8'—C9'—C10'—Fe157.44 (18)
C5—Fe1—C6—C1097.3 (5)C7'—Fe1—C10'—C6'38.48 (9)
C4—Fe1—C6—C1062.3 (5)C9—Fe1—C10'—C6'101.67 (12)
C3—Fe1—C6—C10174 (4)C8—Fe1—C10'—C6'63.02 (13)
C8'—Fe1—C6—C1063.20 (13)C5—Fe1—C10'—C6'116.5 (5)
C1—Fe1—C6—C10140.7 (4)C4—Fe1—C10'—C6'159.0 (4)
C2—Fe1—C6—C10176.8 (4)C10—Fe1—C10'—C6'121.55 (9)
C7—Fe1—C6—C10119.45 (11)C3—Fe1—C10'—C6'170.1 (5)
C10—C6—C7—C80.0C8'—Fe1—C10'—C6'82.94 (13)
Fe1—C6—C7—C858.8 (2)C1—Fe1—C10'—C6'76.8 (4)
C10—C6—C7—Fe158.8 (2)C2—Fe1—C10'—C6'54.6 (10)
C7'—Fe1—C7—C6126.68 (10)C7—Fe1—C10'—C6'20.52 (6)
C9—Fe1—C7—C681.32 (13)C7'—Fe1—C10'—C9'81.50 (14)
C6'—Fe1—C7—C60.3C9—Fe1—C10'—C9'18.3
C8—Fe1—C7—C6119.35 (12)C6'—Fe1—C10'—C9'119.99 (11)
C5—Fe1—C7—C658.2 (4)C8—Fe1—C10'—C9'56.96 (12)
C4—Fe1—C7—C6139 (15)C5—Fe1—C10'—C9'123.5 (5)
C10—Fe1—C7—C637.36 (8)C4—Fe1—C10'—C9'81.0 (5)
C3—Fe1—C7—C6174.3 (4)C10—Fe1—C10'—C9'1.6
C8'—Fe1—C7—C6106.84 (13)C3—Fe1—C10'—C9'50.1 (5)
C1—Fe1—C7—C694.5 (4)C8'—Fe1—C10'—C9'37.05 (9)
C2—Fe1—C7—C6137.9 (3)C1—Fe1—C10'—C9'163.2 (5)
C7'—Fe1—C7—C87.3C2—Fe1—C10'—C9'174.6 (10)
C9—Fe1—C7—C838.03 (9)C7—Fe1—C10'—C9'99.46 (14)
C6'—Fe1—C7—C8119.66 (11)C22—O1—C11—C1125.7 (5)
C5—Fe1—C7—C8177.5 (5)C22—O1—C11—C12113.2 (5)
C4—Fe1—C7—C8102 (15)C2—C1—C11—O133.2 (6)
C10—Fe1—C7—C881.99 (14)C5—C1—C11—O1152.7 (4)
C3—Fe1—C7—C866.4 (4)Fe1—C1—C11—O160.3 (5)
C8'—Fe1—C7—C812.5C2—C1—C11—C1285.3 (5)
C1—Fe1—C7—C8146.2 (4)C5—C1—C11—C1288.8 (5)
C2—Fe1—C7—C8102.7 (4)Fe1—C1—C11—C12178.9 (3)
C6—C7—C8—C90.0C20—N1—C12—C13109.9 (5)
Fe1—C7—C8—C959.60 (19)N2—N1—C12—C1367.3 (5)
C6—C7—C8—Fe159.60 (19)C20—N1—C12—C11121.5 (5)
C7'—Fe1—C8—C9124.08 (10)N2—N1—C12—C1161.3 (5)
C6'—Fe1—C8—C989.10 (12)O1—C11—C12—N168.6 (4)
C5—Fe1—C8—C960 (15)C1—C11—C12—N1171.0 (3)
C4—Fe1—C8—C963.8 (4)O1—C11—C12—C13166.2 (3)
C10—Fe1—C8—C938.05 (9)C1—C11—C12—C1345.8 (5)
C3—Fe1—C8—C9102.9 (3)N1—C12—C13—C1457.9 (5)
C8'—Fe1—C8—C927.8C11—C12—C13—C14177.6 (4)
C1—Fe1—C8—C9173.0 (4)C12—C13—C14—C1579.1 (5)
C2—Fe1—C8—C9147.1 (3)C12—C13—C14—C1998.1 (5)
C7—Fe1—C8—C9118.70 (11)C19—C14—C15—C162.9 (6)
C7'—Fe1—C8—C75.4C13—C14—C15—C16174.3 (5)
C9—Fe1—C8—C7118.70 (11)C14—C15—C16—C171.9 (8)
C6'—Fe1—C8—C729.61 (6)C15—C16—C17—C180.1 (9)
C5—Fe1—C8—C758 (15)C16—C17—C18—C190.8 (9)
C4—Fe1—C8—C7177.5 (4)C15—C14—C19—C182.2 (7)
C10—Fe1—C8—C780.65 (13)C13—C14—C19—C18175.1 (5)
C3—Fe1—C8—C7138.4 (3)C17—C18—C19—C140.3 (9)
C8'—Fe1—C8—C7146.48 (9)C21—N3—C20—N10.2 (6)
C1—Fe1—C8—C754.3 (4)N2—N1—C20—N30.4 (6)
C2—Fe1—C8—C794.2 (3)C12—N1—C20—N3177.9 (4)
C7—C8—C9—C100.0N1—N2—C21—N30.4 (6)
Fe1—C8—C9—C1060.67 (19)C20—N3—C21—N20.2 (6)
C7—C8—C9—Fe160.67 (19)
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds