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The title compound, [Fe(C5H5)(C28H23N2O2)], contains a 1,8-naphthalimide system, substituted in the 4-position with an N-bound piperidine ring. The imide N atom of the naphthalimide group carries a 4-ferrocenylphenyl substituent. The compound crystallizes with the plane of the naphthalimide moiety orthogonal to those of the benzene and cyclo­pentadiene rings, which facilitates intermolecular π stacking interactions between adjacent pairs of naphthalimide rings.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804032271/cv6430sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804032271/cv6430Isup2.hkl
Contains datablock I

CCDC reference: 262258

Key indicators

  • Single-crystal X-ray study
  • T = 163 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.045
  • wR factor = 0.090
  • Data-to-parameter ratio = 12.6

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.92
Author Response: ...This problem is historical and , and since these data were collected for us we had little control over the situation. The problem arose because data were processed with a \q(max) appropriate to harvest all reflections out to the corners of the square chip so anything beyond the largest circle diameter was usually incomplete. Without resorting to another data collection we cannot see an obvious remedy for this situation. Data were certainly collected to beyond 25\% in \q.

Alert level B PLAT022_ALERT_3_B Ratio Unique / Expected Reflections too Low .... 0.89
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.99 PLAT334_ALERT_2_C Small Average Benzene C-C Dist. C13 -C135 1.35 Ang.
1 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker 1999); cell refinement: SAINT (Bruker 1999); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare,1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997) and TITAN2000 (Hunter & Simpson, 1999); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek 1995); software used to prepare material for publication: SHELXL97.

N-(4-ferrocenylphenyl)-4-piperidino-1,8-naphthalimide top
Crystal data top
[Fe(C5H5)(C28H23N2O2)]Z = 2
Mr = 540.42F(000) = 564
Triclinic, P1Dx = 1.517 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.238 (8) ÅCell parameters from 3022 reflections
b = 11.112 (11) Åθ = 2.7–24.7°
c = 12.164 (12) ŵ = 0.68 mm1
α = 93.904 (14)°T = 163 K
β = 100.206 (13)°Plate, orange
γ = 104.154 (15)°0.30 × 0.14 × 0.02 mm
V = 1183.4 (19) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
4329 independent reflections
Radiation source: fine-focus sealed tube2629 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.064
φ and ω scansθmax = 26.4°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Bruker 1999)
h = 118
Tmin = 0.860, Tmax = 1.000k = 1313
11404 measured reflectionsl = 1515
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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091H-atom parameters constrained
S = 0.89 w = 1/[σ2(Fo2) + (0.0393P)2]
where P = (Fo2 + 2Fc2)/3
4329 reflections(Δ/σ)max < 0.001
343 parametersΔρmax = 0.40 e Å3
0 restraintsΔρmin = 0.47 e Å3
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*/Ueq
C10.8659 (4)0.4778 (3)1.2157 (3)0.0208 (8)
C20.8919 (4)0.5487 (3)1.3147 (3)0.0238 (8)
H20.81000.56441.34260.029*
C31.0365 (4)0.5981 (3)1.3751 (3)0.0246 (9)
H31.05080.64551.44410.029*
C41.1583 (4)0.5801 (3)1.3375 (3)0.0212 (8)
N21.3053 (3)0.6290 (2)1.3963 (2)0.0247 (7)
C141.3238 (4)0.6723 (3)1.5135 (3)0.0332 (10)
H14A1.25280.61451.54750.040*
H14B1.30260.75351.52120.040*
C151.4837 (4)0.6819 (4)1.5718 (3)0.0408 (10)
H15A1.49780.71351.65030.049*
H15B1.50220.59961.56840.049*
C161.5946 (4)0.7672 (4)1.5176 (3)0.0458 (11)
H16A1.58480.85181.52950.055*
H16B1.69760.76681.55190.055*
C171.5659 (4)0.7263 (4)1.3951 (3)0.0397 (11)
H17A1.63280.78631.35990.048*
H17B1.58810.64611.38330.048*
C181.4050 (4)0.7157 (3)1.3427 (3)0.0291 (9)
H18A1.38420.79701.35040.035*
H18B1.38710.68711.26310.035*
C51.2508 (4)0.4626 (3)1.2007 (3)0.0224 (8)
H51.34930.49001.24330.027*
C61.2249 (4)0.3864 (3)1.1052 (3)0.0258 (9)
H61.30520.36251.08160.031*
C71.0796 (4)0.3432 (3)1.0421 (3)0.0258 (9)
H71.06230.29250.97460.031*
C80.9629 (4)0.3741 (3)1.0776 (2)0.0199 (8)
C90.9863 (4)0.4530 (3)1.1754 (2)0.0192 (8)
C101.1360 (4)0.5012 (3)1.2369 (2)0.0204 (8)
C110.7118 (4)0.4219 (3)1.1567 (3)0.0224 (8)
O110.6027 (3)0.4381 (2)1.18791 (18)0.0274 (6)
C120.8093 (4)0.3175 (3)1.0157 (3)0.0231 (8)
O120.7817 (3)0.2483 (2)0.93089 (19)0.0405 (7)
N10.6933 (3)0.3424 (2)1.0610 (2)0.0205 (7)
C130.5418 (4)0.2763 (3)1.0066 (3)0.0202 (8)
C1310.4784 (4)0.1651 (3)1.0383 (3)0.0299 (9)
H1310.53220.13281.09580.036*
C1320.3366 (4)0.1007 (3)0.9863 (3)0.0281 (9)
H1320.29310.02391.00860.034*
C1330.2558 (4)0.1464 (3)0.9015 (2)0.0199 (8)
C1340.3216 (3)0.2597 (3)0.8724 (2)0.0208 (8)
H1340.26780.29370.81600.025*
C1350.4641 (3)0.3237 (3)0.9241 (2)0.0202 (8)
H1350.50850.40070.90260.024*
C210.1037 (4)0.0775 (3)0.8447 (3)0.0217 (8)
C220.0197 (4)0.0365 (3)0.8705 (3)0.0262 (9)
H220.05100.08030.92870.031*
C230.1183 (4)0.0728 (3)0.7940 (3)0.0322 (9)
H230.19580.14470.79270.039*
C240.1205 (4)0.0165 (3)0.7204 (3)0.0305 (9)
H240.19930.01470.66040.037*
C250.0144 (4)0.1086 (3)0.7512 (3)0.0255 (9)
H250.04150.17980.71560.031*
Fe10.05688 (6)0.05528 (5)0.71497 (4)0.02217 (16)
C310.2578 (4)0.0667 (3)0.6834 (3)0.0272 (9)
H310.35230.01520.71890.033*
C320.1829 (4)0.1762 (3)0.7180 (3)0.0279 (9)
H320.21850.21150.78110.033*
C330.0455 (4)0.2249 (3)0.6430 (3)0.0261 (9)
H330.02690.29850.64650.031*
C340.0360 (4)0.1439 (3)0.5619 (3)0.0295 (9)
H340.04460.15300.50140.035*
C350.1674 (4)0.0471 (3)0.5867 (3)0.0309 (9)
H350.19100.01980.54520.037*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.021 (2)0.0178 (18)0.0224 (18)0.0040 (16)0.0015 (16)0.0023 (14)
C20.028 (2)0.0218 (18)0.0272 (19)0.0111 (16)0.0133 (17)0.0020 (15)
C30.024 (2)0.0255 (19)0.0246 (18)0.0091 (17)0.0065 (17)0.0044 (15)
C40.022 (2)0.0171 (18)0.0244 (18)0.0044 (16)0.0045 (16)0.0031 (14)
N20.0226 (17)0.0278 (16)0.0188 (14)0.0009 (13)0.0034 (13)0.0006 (12)
C140.028 (2)0.040 (2)0.0258 (19)0.0023 (18)0.0067 (17)0.0025 (17)
C150.034 (2)0.055 (3)0.0254 (19)0.001 (2)0.0022 (18)0.0015 (18)
C160.030 (2)0.062 (3)0.032 (2)0.005 (2)0.0017 (18)0.010 (2)
C170.028 (2)0.048 (2)0.034 (2)0.0067 (19)0.0100 (18)0.0049 (18)
C180.033 (2)0.0258 (19)0.0253 (18)0.0026 (17)0.0114 (17)0.0010 (15)
C50.017 (2)0.0250 (19)0.0239 (18)0.0028 (16)0.0057 (15)0.0023 (15)
C60.022 (2)0.0268 (19)0.0289 (19)0.0056 (16)0.0103 (16)0.0014 (15)
C70.024 (2)0.029 (2)0.0224 (18)0.0035 (17)0.0062 (16)0.0031 (15)
C80.019 (2)0.0210 (18)0.0212 (17)0.0073 (16)0.0053 (15)0.0044 (14)
C90.022 (2)0.0173 (17)0.0196 (17)0.0057 (15)0.0052 (15)0.0053 (14)
C100.021 (2)0.0193 (17)0.0216 (17)0.0052 (16)0.0053 (16)0.0050 (14)
C110.029 (2)0.0187 (18)0.0250 (18)0.0124 (17)0.0106 (17)0.0052 (14)
O110.0223 (15)0.0302 (14)0.0325 (14)0.0102 (12)0.0091 (11)0.0006 (11)
C120.019 (2)0.030 (2)0.0224 (18)0.0077 (17)0.0086 (16)0.0047 (16)
O120.0276 (16)0.0557 (17)0.0309 (14)0.0057 (13)0.0028 (12)0.0191 (13)
N10.0156 (17)0.0240 (15)0.0218 (14)0.0065 (13)0.0019 (12)0.0030 (12)
C130.015 (2)0.0238 (19)0.0223 (17)0.0072 (15)0.0031 (15)0.0015 (14)
C1310.025 (2)0.031 (2)0.032 (2)0.0076 (17)0.0048 (17)0.0125 (16)
C1320.026 (2)0.0229 (19)0.034 (2)0.0029 (17)0.0042 (17)0.0071 (16)
C1330.018 (2)0.0234 (18)0.0189 (17)0.0084 (16)0.0040 (15)0.0024 (14)
C1340.018 (2)0.0282 (19)0.0166 (16)0.0085 (16)0.0011 (14)0.0030 (14)
C1350.017 (2)0.0245 (18)0.0221 (17)0.0077 (16)0.0072 (15)0.0044 (14)
C210.021 (2)0.0235 (19)0.0217 (17)0.0078 (16)0.0056 (15)0.0031 (14)
C220.031 (2)0.0261 (19)0.0200 (17)0.0043 (17)0.0095 (16)0.0060 (15)
C230.020 (2)0.037 (2)0.034 (2)0.0021 (17)0.0090 (17)0.0069 (18)
C240.021 (2)0.035 (2)0.029 (2)0.0064 (17)0.0049 (16)0.0131 (17)
C250.025 (2)0.0254 (19)0.0247 (18)0.0089 (17)0.0002 (16)0.0038 (15)
Fe10.0253 (3)0.0217 (3)0.0183 (2)0.0056 (2)0.0036 (2)0.00126 (19)
C310.021 (2)0.032 (2)0.030 (2)0.0087 (17)0.0090 (17)0.0026 (16)
C320.033 (2)0.030 (2)0.0231 (18)0.0142 (18)0.0030 (17)0.0039 (15)
C330.035 (2)0.0217 (19)0.0235 (18)0.0131 (17)0.0033 (16)0.0000 (15)
C340.039 (2)0.033 (2)0.0180 (17)0.0175 (19)0.0009 (16)0.0057 (15)
C350.042 (3)0.031 (2)0.0260 (19)0.0141 (19)0.0156 (18)0.0078 (16)
Geometric parameters (Å, º) top
C1—C21.344 (4)C13—C1351.342 (4)
C1—C91.370 (5)C13—C1311.345 (4)
C1—C111.439 (5)C131—C1321.346 (4)
C2—C31.365 (4)C131—H1310.9300
C2—H20.9300C132—C1331.366 (4)
C3—C41.341 (4)C132—H1320.9300
C3—H30.9300C133—C1341.357 (4)
C4—N21.376 (4)C133—C211.448 (4)
C4—C101.409 (4)C134—C1351.350 (4)
N2—C181.437 (4)C134—H1340.9300
N2—C141.441 (4)C135—H1350.9300
C14—C151.496 (5)C21—C251.397 (4)
C14—H14A0.9700C21—C221.402 (4)
C14—H14B0.9700C21—Fe11.996 (3)
C15—C161.494 (5)C22—C231.389 (4)
C15—H15A0.9700C22—Fe11.987 (4)
C15—H15B0.9700C22—H220.9300
C16—C171.485 (5)C23—C241.383 (5)
C16—H16A0.9700C23—Fe12.001 (4)
C16—H16B0.9700C23—H230.9300
C17—C181.482 (5)C24—C251.378 (4)
C17—H17A0.9700C24—Fe11.999 (4)
C17—H17B0.9700C24—H240.9300
C18—H18A0.9700C25—Fe11.991 (4)
C18—H18B0.9700C25—H250.9300
C5—C61.339 (4)Fe1—C321.980 (4)
C5—C101.365 (4)Fe1—C311.992 (4)
C5—H50.9300Fe1—C331.994 (4)
C6—C71.376 (4)Fe1—C342.001 (4)
C6—H60.9300Fe1—C352.006 (4)
C7—C81.338 (4)C31—C321.378 (4)
C7—H70.9300C31—C351.380 (4)
C8—C91.380 (4)C31—H310.9300
C8—C121.447 (4)C32—C331.386 (4)
C9—C101.406 (4)C32—H320.9300
C11—O111.187 (4)C33—C341.386 (4)
C11—N11.372 (4)C33—H330.9300
C12—O121.193 (4)C34—C351.382 (5)
C12—N11.364 (4)C34—H340.9300
N1—C131.428 (4)C35—H350.9300
C2—C1—C9119.5 (3)C21—C22—Fe169.72 (18)
C2—C1—C11119.8 (3)C23—C22—H22125.9
C9—C1—C11120.6 (3)C21—C22—H22125.9
C1—C2—C3121.1 (3)Fe1—C22—H22125.8
C1—C2—H2119.4C24—C23—C22108.2 (3)
C3—C2—H2119.4C24—C23—Fe169.7 (2)
C4—C3—C2121.6 (3)C22—C23—Fe169.1 (2)
C4—C3—H3119.2C24—C23—H23125.9
C2—C3—H3119.2C22—C23—H23125.9
C3—C4—N2123.0 (3)Fe1—C23—H23126.9
C3—C4—C10119.1 (3)C25—C24—C23108.1 (3)
N2—C4—C10117.8 (3)C25—C24—Fe169.5 (2)
C4—N2—C18116.5 (3)C23—C24—Fe169.9 (2)
C4—N2—C14116.7 (3)C25—C24—H24125.9
C18—N2—C14111.0 (3)C23—C24—H24125.9
N2—C14—C15109.2 (3)Fe1—C24—H24126.3
N2—C14—H14A109.8C24—C25—C21108.9 (3)
C15—C14—H14A109.8C24—C25—Fe170.1 (2)
N2—C14—H14B109.8C21—C25—Fe169.65 (19)
C15—C14—H14B109.8C24—C25—H25125.5
H14A—C14—H14B108.3C21—C25—H25125.5
C16—C15—C14110.4 (3)Fe1—C25—H25126.3
C16—C15—H15A109.6C32—Fe1—C22104.70 (14)
C14—C15—H15A109.6C32—Fe1—C25155.51 (13)
C16—C15—H15B109.6C22—Fe1—C2568.67 (14)
C14—C15—H15B109.6C32—Fe1—C3140.59 (13)
H15A—C15—H15B108.1C22—Fe1—C31122.36 (14)
C17—C16—C15110.3 (3)C25—Fe1—C31121.76 (14)
C17—C16—H16A109.6C32—Fe1—C3340.83 (13)
C15—C16—H16A109.6C22—Fe1—C33119.13 (14)
C17—C16—H16B109.6C25—Fe1—C33163.07 (12)
C15—C16—H16B109.6C31—Fe1—C3368.48 (14)
H16A—C16—H16B108.1C32—Fe1—C21118.53 (14)
C18—C17—C16110.5 (3)C22—Fe1—C2141.21 (13)
C18—C17—H17A109.5C25—Fe1—C2141.03 (12)
C16—C17—H17A109.5C31—Fe1—C21105.82 (14)
C18—C17—H17B109.5C33—Fe1—C21154.23 (13)
C16—C17—H17B109.5C32—Fe1—C24160.97 (13)
H17A—C17—H17B108.1C22—Fe1—C2468.54 (14)
N2—C18—C17109.8 (3)C25—Fe1—C2440.42 (12)
N2—C18—H18A109.7C31—Fe1—C24158.00 (14)
C17—C18—H18A109.7C33—Fe1—C24125.60 (14)
N2—C18—H18B109.7C21—Fe1—C2468.85 (14)
C17—C18—H18B109.7C32—Fe1—C3468.31 (14)
H18A—C18—H18B108.2C22—Fe1—C34155.87 (13)
C6—C5—C10121.5 (3)C25—Fe1—C34127.05 (14)
C6—C5—H5119.2C31—Fe1—C3468.20 (14)
C10—C5—H5119.2C33—Fe1—C3440.60 (13)
C5—C6—C7120.0 (3)C21—Fe1—C34162.61 (13)
C5—C6—H6120.0C24—Fe1—C34110.20 (14)
C7—C6—H6120.0C32—Fe1—C23123.09 (15)
C8—C7—C6120.2 (3)C22—Fe1—C2340.76 (13)
C8—C7—H7119.9C25—Fe1—C2368.09 (15)
C6—C7—H7119.9C31—Fe1—C23159.45 (14)
C7—C8—C9121.0 (3)C33—Fe1—C23107.17 (15)
C7—C8—C12119.1 (3)C21—Fe1—C2368.90 (14)
C9—C8—C12119.8 (3)C24—Fe1—C2340.44 (14)
C1—C9—C8120.9 (3)C34—Fe1—C23122.43 (15)
C1—C9—C10120.4 (3)C32—Fe1—C3567.95 (14)
C8—C9—C10118.5 (3)C22—Fe1—C35160.32 (13)
C5—C10—C9118.6 (3)C25—Fe1—C35110.01 (14)
C5—C10—C4123.2 (3)C31—Fe1—C3540.37 (13)
C9—C10—C4118.0 (3)C33—Fe1—C3568.05 (14)
O11—C11—N1119.4 (3)C21—Fe1—C35124.77 (14)
O11—C11—C1124.0 (3)C24—Fe1—C35124.08 (15)
N1—C11—C1116.6 (3)C34—Fe1—C3540.33 (13)
O12—C12—N1120.0 (3)C23—Fe1—C35158.47 (13)
O12—C12—C8122.9 (3)C32—C31—C35107.8 (3)
N1—C12—C8117.0 (3)C32—C31—Fe169.2 (2)
C12—N1—C11124.9 (3)C35—C31—Fe170.4 (2)
C12—N1—C13117.0 (3)C32—C31—H31126.1
C11—N1—C13118.0 (3)C35—C31—H31126.1
C135—C13—C131120.3 (3)Fe1—C31—H31125.9
C135—C13—N1120.5 (3)C31—C32—C33108.5 (3)
C131—C13—N1119.2 (3)C31—C32—Fe170.2 (2)
C13—C131—C132119.8 (3)C33—C32—Fe170.1 (2)
C13—C131—H131120.1C31—C32—H32125.8
C132—C131—H131120.1C33—C32—H32125.8
C131—C132—C133121.0 (3)Fe1—C32—H32125.5
C131—C132—H132119.5C32—C33—C34107.4 (3)
C133—C132—H132119.5C32—C33—Fe169.03 (19)
C134—C133—C132118.0 (3)C34—C33—Fe170.0 (2)
C134—C133—C21120.6 (3)C32—C33—H33126.3
C132—C133—C21121.4 (3)C34—C33—H33126.3
C135—C134—C133120.8 (3)Fe1—C33—H33126.3
C135—C134—H134119.6C35—C34—C33108.0 (3)
C133—C134—H134119.6C35—C34—Fe170.04 (19)
C13—C135—C134120.0 (3)C33—C34—Fe169.4 (2)
C13—C135—H135120.0C35—C34—H34126.0
C134—C135—H135120.0C33—C34—H34126.0
C25—C21—C22106.6 (3)Fe1—C34—H34126.1
C25—C21—C133127.0 (3)C31—C35—C34108.3 (3)
C22—C21—C133126.3 (3)C31—C35—Fe169.3 (2)
C25—C21—Fe169.32 (19)C34—C35—Fe169.6 (2)
C22—C21—Fe169.08 (18)C31—C35—H35125.8
C133—C21—Fe1124.6 (2)C34—C35—H35125.8
C23—C22—C21108.2 (3)Fe1—C35—H35126.9
C23—C22—Fe170.2 (2)
C9—C1—C2—C31.1 (5)C25—C21—Fe1—C2437.0 (2)
C11—C1—C2—C3176.9 (3)C22—C21—Fe1—C2481.2 (2)
C1—C2—C3—C41.3 (5)C133—C21—Fe1—C24158.4 (3)
C2—C3—C4—N2179.8 (3)C25—C21—Fe1—C3453.2 (5)
C2—C3—C4—C104.4 (5)C22—C21—Fe1—C34171.4 (4)
C3—C4—N2—C18118.0 (4)C133—C21—Fe1—C3468.2 (6)
C10—C4—N2—C1866.1 (4)C25—C21—Fe1—C2380.5 (2)
C3—C4—N2—C1416.3 (5)C22—C21—Fe1—C2337.7 (2)
C10—C4—N2—C14159.5 (3)C133—C21—Fe1—C23158.1 (3)
C4—N2—C14—C15161.4 (3)C25—C21—Fe1—C3580.6 (2)
C18—N2—C14—C1561.9 (4)C22—C21—Fe1—C35161.3 (2)
N2—C14—C15—C1657.5 (4)C133—C21—Fe1—C3540.8 (3)
C14—C15—C16—C1754.3 (5)C25—C24—Fe1—C32154.2 (4)
C15—C16—C17—C1854.4 (5)C23—C24—Fe1—C3234.8 (5)
C4—N2—C18—C17160.9 (3)C25—C24—Fe1—C2281.9 (2)
C14—N2—C18—C1762.3 (4)C23—C24—Fe1—C2237.50 (19)
C16—C17—C18—N258.0 (4)C23—C24—Fe1—C25119.4 (3)
C10—C5—C6—C71.1 (5)C25—C24—Fe1—C3142.3 (4)
C5—C6—C7—C82.1 (5)C23—C24—Fe1—C31161.7 (3)
C6—C7—C8—C92.4 (5)C25—C24—Fe1—C33166.91 (19)
C6—C7—C8—C12173.8 (3)C23—C24—Fe1—C3373.7 (2)
C2—C1—C9—C8175.9 (3)C25—C24—Fe1—C2137.50 (19)
C11—C1—C9—C80.1 (5)C23—C24—Fe1—C2181.9 (2)
C2—C1—C9—C100.1 (5)C25—C24—Fe1—C34123.9 (2)
C11—C1—C9—C10175.9 (3)C23—C24—Fe1—C34116.7 (2)
C7—C8—C9—C1175.5 (3)C25—C24—Fe1—C23119.4 (3)
C12—C8—C9—C10.6 (5)C25—C24—Fe1—C3581.0 (2)
C7—C8—C9—C100.5 (5)C23—C24—Fe1—C35159.66 (19)
C12—C8—C9—C10176.6 (3)C24—C23—Fe1—C32167.17 (19)
C6—C5—C10—C94.0 (5)C22—C23—Fe1—C3273.0 (2)
C6—C5—C10—C4179.2 (3)C24—C23—Fe1—C22119.8 (3)
C1—C9—C10—C5172.4 (3)C24—C23—Fe1—C2537.51 (19)
C8—C9—C10—C53.6 (4)C22—C23—Fe1—C2582.3 (2)
C1—C9—C10—C43.0 (4)C24—C23—Fe1—C31160.4 (3)
C8—C9—C10—C4179.1 (3)C22—C23—Fe1—C3140.6 (5)
C3—C4—C10—C5170.0 (3)C24—C23—Fe1—C33125.2 (2)
N2—C4—C10—C56.0 (5)C22—C23—Fe1—C33115.0 (2)
C3—C4—C10—C95.2 (4)C24—C23—Fe1—C2181.8 (2)
N2—C4—C10—C9178.8 (3)C22—C23—Fe1—C2138.1 (2)
C2—C1—C11—O113.1 (5)C22—C23—Fe1—C24119.8 (3)
C9—C1—C11—O11178.9 (3)C24—C23—Fe1—C3483.4 (2)
C2—C1—C11—N1174.7 (3)C22—C23—Fe1—C34156.8 (2)
C9—C1—C11—N11.1 (4)C24—C23—Fe1—C3551.7 (5)
C7—C8—C12—O123.6 (5)C22—C23—Fe1—C35171.5 (3)
C9—C8—C12—O12179.7 (3)C22—Fe1—C31—C3273.9 (2)
C7—C8—C12—N1173.8 (3)C25—Fe1—C31—C32157.30 (19)
C9—C8—C12—N12.4 (4)C33—Fe1—C31—C3237.83 (19)
O12—C12—N1—C11178.8 (3)C21—Fe1—C31—C32115.6 (2)
C8—C12—N1—C113.8 (4)C24—Fe1—C31—C32171.8 (3)
O12—C12—N1—C133.9 (4)C34—Fe1—C31—C3281.7 (2)
C8—C12—N1—C13173.5 (3)C23—Fe1—C31—C3243.7 (5)
O11—C11—N1—C12178.9 (3)C35—Fe1—C31—C32118.8 (3)
C1—C11—N1—C123.1 (4)C32—Fe1—C31—C35118.8 (3)
O11—C11—N1—C133.8 (4)C22—Fe1—C31—C35167.3 (2)
C1—C11—N1—C13174.1 (3)C25—Fe1—C31—C3583.9 (2)
C12—N1—C13—C13590.2 (4)C33—Fe1—C31—C3581.0 (2)
C11—N1—C13—C13592.3 (4)C21—Fe1—C31—C35125.6 (2)
C12—N1—C13—C13189.1 (4)C24—Fe1—C31—C3553.0 (4)
C11—N1—C13—C13188.4 (4)C34—Fe1—C31—C3537.2 (2)
C135—C13—C131—C1320.5 (5)C23—Fe1—C31—C35162.5 (4)
N1—C13—C131—C132178.8 (3)C35—C31—C32—C330.1 (4)
C13—C131—C132—C1330.1 (6)Fe1—C31—C32—C3359.9 (2)
C131—C132—C133—C1341.1 (5)C35—C31—C32—Fe160.1 (3)
C131—C132—C133—C21179.6 (3)C22—Fe1—C32—C31123.0 (2)
C132—C133—C134—C1351.5 (5)C25—Fe1—C32—C3152.3 (4)
C21—C133—C134—C135179.2 (3)C33—Fe1—C32—C31119.2 (3)
C131—C13—C135—C1340.0 (5)C21—Fe1—C32—C3180.9 (2)
N1—C13—C135—C134179.2 (3)C24—Fe1—C32—C31170.6 (4)
C133—C134—C135—C131.0 (5)C34—Fe1—C32—C3181.4 (2)
C134—C133—C21—C256.4 (5)C23—Fe1—C32—C31163.19 (19)
C132—C133—C21—C25174.3 (3)C35—Fe1—C32—C3137.76 (19)
C134—C133—C21—C22176.3 (3)C22—Fe1—C32—C33117.8 (2)
C132—C133—C21—C223.0 (5)C25—Fe1—C32—C33171.6 (3)
C134—C133—C21—Fe195.5 (4)C31—Fe1—C32—C33119.2 (3)
C132—C133—C21—Fe185.2 (4)C21—Fe1—C32—C33159.82 (19)
C25—C21—C22—C230.4 (4)C24—Fe1—C32—C3351.3 (5)
C133—C21—C22—C23178.1 (3)C34—Fe1—C32—C3337.9 (2)
Fe1—C21—C22—C2359.8 (2)C23—Fe1—C32—C3377.6 (2)
C25—C21—C22—Fe159.4 (2)C35—Fe1—C32—C3381.5 (2)
C133—C21—C22—Fe1118.3 (3)C31—C32—C33—C340.3 (4)
C21—C22—C23—C240.6 (4)Fe1—C32—C33—C3459.7 (2)
Fe1—C22—C23—C2458.9 (3)C31—C32—C33—Fe160.0 (2)
C21—C22—C23—Fe159.5 (2)C22—Fe1—C33—C3278.4 (2)
C22—C23—C24—C250.6 (4)C25—Fe1—C33—C32168.0 (4)
Fe1—C23—C24—C2559.2 (3)C31—Fe1—C33—C3237.6 (2)
C22—C23—C24—Fe158.5 (3)C21—Fe1—C33—C3244.2 (4)
C23—C24—C25—C210.4 (4)C24—Fe1—C33—C32161.8 (2)
Fe1—C24—C25—C2159.0 (2)C34—Fe1—C33—C32118.8 (3)
C23—C24—C25—Fe159.4 (3)C23—Fe1—C33—C32121.1 (2)
C22—C21—C25—C240.0 (4)C35—Fe1—C33—C3281.2 (2)
C133—C21—C25—C24177.7 (3)C32—Fe1—C33—C34118.8 (3)
Fe1—C21—C25—C2459.3 (2)C22—Fe1—C33—C34162.8 (2)
C22—C21—C25—Fe159.3 (2)C25—Fe1—C33—C3449.2 (6)
C133—C21—C25—Fe1118.4 (4)C31—Fe1—C33—C3481.2 (2)
C23—C22—Fe1—C32124.1 (2)C21—Fe1—C33—C34163.0 (3)
C21—C22—Fe1—C32116.7 (2)C24—Fe1—C33—C3479.5 (3)
C23—C22—Fe1—C2580.8 (2)C23—Fe1—C33—C34120.1 (2)
C21—C22—Fe1—C2538.4 (2)C35—Fe1—C33—C3437.6 (2)
C23—C22—Fe1—C31164.3 (2)C32—C33—C34—C350.6 (4)
C21—C22—Fe1—C3176.5 (2)Fe1—C33—C34—C3559.7 (2)
C23—C22—Fe1—C3382.6 (2)C32—C33—C34—Fe159.1 (2)
C21—C22—Fe1—C33158.2 (2)C32—Fe1—C34—C3581.0 (2)
C23—C22—Fe1—C21119.2 (3)C22—Fe1—C34—C35158.3 (3)
C23—C22—Fe1—C2437.2 (2)C25—Fe1—C34—C3576.9 (3)
C21—C22—Fe1—C2482.0 (2)C31—Fe1—C34—C3537.2 (2)
C23—C22—Fe1—C3454.5 (4)C33—Fe1—C34—C35119.1 (3)
C21—C22—Fe1—C34173.7 (3)C21—Fe1—C34—C3535.7 (6)
C21—C22—Fe1—C23119.2 (3)C24—Fe1—C34—C35119.3 (2)
C23—C22—Fe1—C35170.7 (4)C23—Fe1—C34—C35162.6 (2)
C21—C22—Fe1—C3551.5 (5)C32—Fe1—C34—C3338.1 (2)
C24—C25—Fe1—C32160.0 (3)C22—Fe1—C34—C3339.2 (4)
C21—C25—Fe1—C3239.9 (4)C25—Fe1—C34—C33164.0 (2)
C24—C25—Fe1—C2281.5 (2)C31—Fe1—C34—C3381.9 (2)
C21—C25—Fe1—C2238.6 (2)C21—Fe1—C34—C33154.8 (4)
C24—C25—Fe1—C31162.7 (2)C24—Fe1—C34—C33121.6 (2)
C21—C25—Fe1—C3177.1 (2)C23—Fe1—C34—C3378.2 (3)
C24—C25—Fe1—C3339.2 (6)C35—Fe1—C34—C33119.1 (3)
C21—C25—Fe1—C33159.4 (4)C32—C31—C35—C340.5 (4)
C24—C25—Fe1—C21120.1 (3)Fe1—C31—C35—C3458.8 (3)
C21—C25—Fe1—C24120.1 (3)C32—C31—C35—Fe159.3 (2)
C24—C25—Fe1—C3477.3 (3)C33—C34—C35—C310.7 (4)
C21—C25—Fe1—C34162.5 (2)Fe1—C34—C35—C3158.6 (3)
C24—C25—Fe1—C2337.5 (2)C33—C34—C35—Fe159.3 (3)
C21—C25—Fe1—C2382.6 (2)C32—Fe1—C35—C3137.95 (19)
C24—C25—Fe1—C35119.5 (2)C22—Fe1—C35—C3133.4 (5)
C21—C25—Fe1—C35120.4 (2)C25—Fe1—C35—C31115.9 (2)
C25—C21—Fe1—C32162.40 (19)C33—Fe1—C35—C3182.1 (2)
C22—C21—Fe1—C3279.5 (2)C21—Fe1—C35—C3172.3 (2)
C133—C21—Fe1—C3241.0 (3)C24—Fe1—C35—C31158.83 (19)
C25—C21—Fe1—C22118.1 (3)C34—Fe1—C35—C31120.0 (3)
C133—C21—Fe1—C22120.5 (4)C23—Fe1—C35—C31163.3 (4)
C22—C21—Fe1—C25118.1 (3)C32—Fe1—C35—C3482.0 (2)
C133—C21—Fe1—C25121.4 (4)C22—Fe1—C35—C34153.4 (4)
C25—C21—Fe1—C31120.5 (2)C25—Fe1—C35—C34124.2 (2)
C22—C21—Fe1—C31121.4 (2)C31—Fe1—C35—C34120.0 (3)
C133—C21—Fe1—C310.9 (3)C33—Fe1—C35—C3437.8 (2)
C25—C21—Fe1—C33166.3 (3)C21—Fe1—C35—C34167.7 (2)
C22—C21—Fe1—C3348.2 (4)C24—Fe1—C35—C3481.2 (3)
C133—C21—Fe1—C3372.2 (4)C23—Fe1—C35—C3443.3 (5)
 

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