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The title compound, [Fe(C5H5)(C15H18N)], has been synthesized as a precursor of ferrocenylamino­phosphine and its crystal structure determined. The substituted cyclo­penta­dienyl plane is nearly perpendicular to the plane of the benzene ring [dihedral angle = 84.9 (2)°].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680503936X/hg6271sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680503936X/hg6271Isup2.hkl
Contains datablock I

CCDC reference: 296568

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • Disorder in main residue
  • R factor = 0.027
  • wR factor = 0.078
  • Data-to-parameter ratio = 12.0

checkCIF/PLATON results

No syntax errors found



Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.635 0.836 Tmin(prime) and Tmax expected: 0.707 0.836 RR(prime) = 0.899 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.89 PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C8' PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Fe1 PLAT301_ALERT_3_C Main Residue Disorder ......................... 19.00 Perc. PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 45 C10'-FE1 -C2 -C1 -18.00 12.00 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 -C3 102.00 12.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 120 C8' -FE1 -C5 -C4 13.00 0.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 130 C8' -FE1 -C5 -C1 12.00 0.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 255 C3 -FE1 -C6' -C10' -82.00 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 ... # 266 C3 -FE1 -C6' -C7' 159.00 13.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 280 C4 -FE1 -C7' -C6' 1.00 17.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 292 C4 -FE1 -C7' -C8' -119.00 17.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 303 C5 -FE1 -C8' -C9' 6.00 0.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 314 C5 -FE1 -C8' -C7' 6.00 0.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 327 C1 -FE1 -C9' -C8' 88.00 16.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 338 C1 -FE1 -C9' -C10' -34.00 16.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 358 C2 -FE1 -C10'-C6' 77.00 12.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 369 C2 -FE1 -C10'-C9' -166.00 11.00 1.555 1.555 1.555 1.555 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 4
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 22 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 15 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

Cyclometallated compounds are widely used in organic synthesis such as the Heck and Suzuki reactions (Dupont et al. 2005). As a part of our ongoing investigations on cyclometallation and applications in asymmetric catalysis of ferrocenylamines (Wang et al., 2005), a new compound, (I), has been prepared and we report here its crystal structure. The deviation of atom N1 from the C11/C12/C13 plane is 0.4580 (1) Å. The methylene atom C11 is coplanar with the benzene plane [deviation = 0.0204 (3) Å], whereas the methyl atom C12 lies out of the benzene plane by 1.8453 Å. The cyclopentadienyl plane nearly perpendicular to the plane of the benzene ring [dihedral angle = 84.9 (2)°].

Experimental top

To a vigorously stirred solution of N-(4-methylbenzyl) aminomethylferrocene (319 mg, 1 mmol) and 37% aqueous formaldehyde (1 ml, 12.5 mmol) in 20 ml of acetonitrile was added sodium cyanoborohydride (190 mg, 3 mmol). After 30 min, glacial acid was added dropwise until the pH was 7. The mixture was stirred at room temperature for 6 h. The solvent was removed and 2 N sodium hydroxide (20 ml) was then added to the residue. The mixture was extracted with diethyl ether. The organic layer was dried over anhydrous sodium sulfate and the solvent was removed to give the crude product, which was purified by column chromatography to afford (I) (yield 70%). A yellow single-crystal suitable for X-ray analysis was obtained by slow evaporation of a dichloromethane /petroleum ether solution at room temperature over a period of a week. Analysis calculated for C20H23FeN: C 72.08, H 6.96, N 4.20%; found: C 72.11, H 6.71, N 4.36%.

Refinement top

The C6-containing cyclopentadienyl plane is disordered over two positions; site-occupancy factors were refined and converged to 0.75 and 1/4, respectively. The disordered ferrocenyl ring was refined as a regular pentagon. All H atoms were initially located in a difference Fourier map. The methyl H atoms were then constrained to an ideal geometry with C—H distances of 0.96 Å and Uiso(H) = 1.5Ueq(C), but each group was allowed to rotate freely about its C—C bond. All other H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms with C—H distances in the range 0.93–0.98 Å and Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SMART; data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), shown with 35% probability displacement ellipsoids (arbitrary spheres for H atoms). The minor component of the disordered ferrocenyl ring has been omitted for clarity.
1-[N-Methyl-N-(4-methylbenzyl)aminomethyl]ferrocene top
Crystal data top
[Fe(C5H5)(C15H18N)]F(000) = 704
Mr = 333.24Dx = 1.320 Mg m3
Monoclinic, P21/nMelting point: 308 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 14.8570 (14) ÅCell parameters from 3999 reflections
b = 5.9690 (5) Åθ = 2.2–27.6°
c = 19.3667 (18) ŵ = 0.90 mm1
β = 102.530 (1)°T = 293 K
V = 1676.6 (3) Å3Block, red
Z = 40.38 × 0.26 × 0.20 mm
Data collection top
Bruker APEX-II CCD area-detector
diffractometer
2950 independent reflections
Radiation source: fine-focus sealed tube2436 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.017
ϕ and ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1714
Tmin = 0.635, Tmax = 0.836k = 75
8678 measured reflectionsl = 2123
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)] = 0.027Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.078H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0439P)2 + 0.3349P]
where P = (Fo2 + 2Fc2)/3
2950 reflections(Δ/σ)max = 0.001
246 parametersΔρmax = 0.18 e Å3
20 restraintsΔρmin = 0.31 e Å3
Crystal data top
[Fe(C5H5)(C15H18N)]V = 1676.6 (3) Å3
Mr = 333.24Z = 4
Monoclinic, P21/nMo Kα radiation
a = 14.8570 (14) ŵ = 0.90 mm1
b = 5.9690 (5) ÅT = 293 K
c = 19.3667 (18) Å0.38 × 0.26 × 0.20 mm
β = 102.530 (1)°
Data collection top
Bruker APEX-II CCD area-detector
diffractometer
2950 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2436 reflections with I > 2σ(I)
Tmin = 0.635, Tmax = 0.836Rint = 0.017
8678 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.02720 restraints
wR(F2) = 0.078H-atom parameters constrained
S = 1.06Δρmax = 0.18 e Å3
2950 reflectionsΔρmin = 0.31 e Å3
246 parameters
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)
Fe10.441217 (16)0.74972 (4)0.170003 (12)0.03917 (11)
N10.72596 (10)0.7455 (2)0.13968 (7)0.0408 (3)
C10.55808 (12)0.7481 (3)0.13146 (9)0.0393 (4)
C20.52888 (12)0.9706 (3)0.13838 (9)0.0431 (4)
H20.56461.08710.16790.052*
C30.43861 (12)0.9960 (3)0.09642 (9)0.0486 (4)
H30.40121.13270.09160.058*
C40.41231 (13)0.7894 (3)0.06274 (9)0.0506 (5)
H40.35310.75730.03060.061*
C50.48541 (12)0.6366 (3)0.08376 (8)0.0452 (4)
H50.48590.48010.06860.054*
C60.4715 (5)0.6005 (18)0.2657 (5)0.070 (2)0.75
H6A0.53130.53650.28850.084*0.75
C70.4429 (5)0.8217 (16)0.2732 (4)0.069 (2)0.75
H7A0.47890.93970.30170.083*0.75
C80.3526 (5)0.8432 (13)0.2306 (5)0.069 (2)0.75
H8A0.31510.97970.22460.083*0.75
C90.3265 (5)0.636 (2)0.1986 (3)0.073 (2)0.75
H9A0.26750.60200.16650.088*0.75
C100.3997 (10)0.4864 (7)0.2208 (5)0.075 (2)0.75
H10A0.40080.32900.20660.090*0.75
C6'0.4442 (11)0.493 (3)0.2421 (10)0.045 (4)0.25
H6'A0.48220.35740.24560.054*0.25
C7'0.4694 (12)0.696 (5)0.2785 (9)0.060 (7)0.25
H7'A0.52810.72700.31150.072*0.25
C8'0.396 (2)0.8501 (18)0.2578 (12)0.073 (9)0.25
H8'A0.39421.00450.27460.088*0.25
C9'0.3228 (12)0.735 (4)0.2130 (12)0.062 (7)0.25
H9'A0.26220.79780.19160.075*0.25
C10'0.3550 (11)0.519 (3)0.1999 (9)0.051 (4)0.25
H10B0.31960.40410.16940.061*0.25
C110.64944 (12)0.6492 (3)0.16616 (9)0.0468 (4)
H11A0.66010.67390.21680.056*
H11B0.64770.48880.15810.056*
C120.81258 (13)0.6482 (4)0.17816 (10)0.0595 (5)
H12A0.81110.48880.17150.089*
H12B0.82070.68160.22760.089*
H12C0.86290.71040.16060.089*
C130.71443 (12)0.7112 (3)0.06401 (9)0.0440 (4)
H13A0.65120.74610.04120.053*
H13B0.72470.55410.05540.053*
C140.77810 (10)0.8504 (3)0.03033 (8)0.0390 (4)
C150.79765 (13)0.7837 (3)0.03333 (10)0.0477 (4)
H150.77510.64740.05310.057*
C160.85015 (13)0.9163 (3)0.06798 (10)0.0534 (5)
H160.86180.86800.11080.064*
C170.88564 (12)1.1193 (3)0.04019 (9)0.0478 (4)
C180.86671 (13)1.1843 (3)0.02389 (10)0.0495 (4)
H180.89021.31920.04420.059*
C190.81356 (12)1.0524 (3)0.05836 (9)0.0461 (4)
H190.80161.10080.10110.055*
C200.94341 (17)1.2627 (3)0.07785 (13)0.0659 (6)
H20A0.93461.41780.06790.099*
H20B0.92511.23750.12790.099*
H20C1.00731.22420.06180.099*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.04312 (17)0.03984 (17)0.03690 (16)0.00335 (10)0.01380 (11)0.00171 (10)
N10.0373 (7)0.0470 (9)0.0372 (7)0.0019 (6)0.0062 (6)0.0043 (6)
C10.0416 (9)0.0445 (10)0.0339 (8)0.0027 (7)0.0126 (7)0.0039 (7)
C20.0476 (10)0.0401 (10)0.0407 (9)0.0088 (8)0.0073 (7)0.0029 (7)
C30.0484 (10)0.0486 (11)0.0475 (10)0.0018 (8)0.0076 (8)0.0103 (8)
C40.0458 (10)0.0659 (13)0.0372 (9)0.0082 (9)0.0028 (8)0.0001 (8)
C50.0556 (11)0.0455 (10)0.0377 (9)0.0094 (9)0.0171 (8)0.0065 (8)
C60.088 (5)0.092 (6)0.039 (5)0.023 (4)0.030 (3)0.017 (4)
C70.080 (5)0.086 (5)0.050 (3)0.016 (3)0.033 (3)0.016 (3)
C80.077 (5)0.066 (4)0.079 (5)0.005 (3)0.048 (4)0.002 (4)
C90.058 (4)0.101 (7)0.071 (3)0.023 (4)0.035 (3)0.010 (5)
C100.128 (9)0.046 (2)0.067 (7)0.014 (4)0.055 (5)0.005 (3)
C6'0.043 (8)0.066 (10)0.023 (7)0.004 (6)0.001 (5)0.001 (5)
C7'0.073 (12)0.088 (18)0.025 (5)0.027 (11)0.020 (7)0.022 (11)
C8'0.14 (3)0.046 (8)0.052 (16)0.024 (14)0.057 (17)0.016 (8)
C9'0.067 (11)0.062 (14)0.077 (15)0.030 (10)0.056 (11)0.024 (12)
C10'0.036 (9)0.069 (11)0.045 (7)0.004 (6)0.002 (6)0.012 (7)
C110.0499 (10)0.0499 (10)0.0414 (9)0.0034 (8)0.0119 (8)0.0098 (8)
C120.0460 (10)0.0727 (14)0.0547 (11)0.0088 (10)0.0005 (8)0.0099 (11)
C130.0415 (9)0.0499 (10)0.0405 (9)0.0041 (8)0.0090 (7)0.0034 (7)
C140.0339 (8)0.0433 (9)0.0393 (9)0.0031 (7)0.0067 (7)0.0012 (8)
C150.0512 (10)0.0492 (11)0.0441 (10)0.0005 (8)0.0134 (8)0.0059 (8)
C160.0602 (11)0.0606 (12)0.0445 (10)0.0052 (9)0.0226 (9)0.0014 (9)
C170.0458 (10)0.0506 (12)0.0502 (10)0.0079 (8)0.0177 (8)0.0102 (9)
C180.0527 (11)0.0428 (10)0.0550 (11)0.0030 (8)0.0162 (9)0.0007 (9)
C190.0504 (10)0.0478 (11)0.0426 (9)0.0013 (8)0.0159 (8)0.0034 (8)
C200.0697 (14)0.0644 (15)0.0716 (14)0.0005 (10)0.0328 (12)0.0151 (10)
Geometric parameters (Å, º) top
Fe1—C62.018 (6)C10—H10A0.9800
Fe1—C92.019 (5)C6'—C10'1.406 (8)
Fe1—C102.020 (4)C6'—C7'1.414 (8)
Fe1—C82.023 (7)C6'—H6'A0.9800
Fe1—C12.0334 (17)C7'—C8'1.415 (9)
Fe1—C52.0377 (17)C7'—H7'A0.9800
Fe1—C72.038 (8)C8'—C9'1.413 (9)
Fe1—C22.0386 (17)C8'—H8'A0.9800
Fe1—C42.0418 (18)C9'—C10'1.417 (8)
Fe1—C32.0419 (18)C9'—H9'A0.9800
Fe1—C10'2.048 (18)C10'—H10B0.9800
Fe1—C8'2.048 (17)C11—H11A0.9700
N1—C131.453 (2)C11—H11B0.9700
N1—C121.460 (2)C12—H12A0.9600
N1—C111.462 (2)C12—H12B0.9600
C1—C21.413 (2)C12—H12C0.9600
C1—C51.424 (2)C13—C141.509 (2)
C1—C111.499 (2)C13—H13A0.9700
C2—C31.417 (2)C13—H13B0.9700
C2—H20.9800C14—C191.379 (2)
C3—C41.410 (3)C14—C151.385 (2)
C3—H30.9800C15—C161.383 (3)
C4—C51.409 (3)C15—H150.9300
C4—H40.9800C16—C171.383 (3)
C5—H50.9800C16—H160.9300
C6—C101.398 (6)C17—C181.386 (3)
C6—C71.404 (7)C17—C201.508 (3)
C6—H6A0.9800C18—C191.385 (3)
C7—C81.420 (7)C18—H180.9300
C7—H7A0.9800C19—H190.9300
C8—C91.398 (6)C20—H20A0.9600
C8—H8A0.9800C20—H20B0.9600
C9—C101.401 (6)C20—H20C0.9600
C9—H9A0.9800
C6—Fe1—C968.5 (2)C7—C6—Fe170.5 (4)
C6—Fe1—C1040.52 (19)C10—C6—H6A125.8
C9—Fe1—C1040.60 (18)C7—C6—H6A125.8
C6—Fe1—C868.4 (2)Fe1—C6—H6A125.8
C9—Fe1—C840.48 (18)C6—C7—C8107.1 (5)
C10—Fe1—C868.0 (2)C6—C7—Fe169.0 (4)
C6—Fe1—C1107.29 (18)C8—C7—Fe168.9 (5)
C9—Fe1—C1159.6 (3)C6—C7—H7A126.4
C10—Fe1—C1123.4 (3)C8—C7—H7A126.4
C8—Fe1—C1158.3 (3)Fe1—C7—H7A126.4
C6—Fe1—C5124.0 (2)C9—C8—C7108.3 (5)
C9—Fe1—C5123.7 (2)C9—C8—Fe169.6 (4)
C10—Fe1—C5109.15 (13)C7—C8—Fe170.1 (5)
C8—Fe1—C5158.9 (3)C9—C8—H8A125.9
C1—Fe1—C540.96 (7)C7—C8—H8A125.9
C6—Fe1—C740.5 (2)Fe1—C8—H8A125.9
C9—Fe1—C768.5 (2)C8—C9—C10107.8 (4)
C10—Fe1—C768.1 (2)C8—C9—Fe169.9 (4)
C8—Fe1—C740.92 (18)C10—C9—Fe169.8 (3)
C1—Fe1—C7122.1 (2)C8—C9—H9A126.1
C5—Fe1—C7159.3 (3)C10—C9—H9A126.1
C6—Fe1—C2122.1 (3)Fe1—C9—H9A126.1
C9—Fe1—C2158.6 (4)C6—C10—C9108.4 (4)
C10—Fe1—C2158.7 (4)C6—C10—Fe169.6 (3)
C8—Fe1—C2122.3 (3)C9—C10—Fe169.6 (3)
C1—Fe1—C240.60 (7)C6—C10—H10A125.8
C5—Fe1—C268.13 (7)C9—C10—H10A125.8
C7—Fe1—C2106.6 (2)Fe1—C10—H10A125.8
C6—Fe1—C4160.4 (3)C10'—C6'—C7'108.0 (6)
C9—Fe1—C4108.31 (19)C10'—C6'—Fe169.3 (12)
C10—Fe1—C4124.5 (3)C7'—C6'—Fe170.4 (10)
C8—Fe1—C4122.6 (2)C10'—C6'—H6'A126.0
C1—Fe1—C468.59 (7)C7'—C6'—H6'A126.0
C5—Fe1—C440.41 (8)Fe1—C6'—H6'A126.0
C7—Fe1—C4158.1 (3)C6'—C7'—C8'108.1 (5)
C2—Fe1—C468.06 (7)C6'—C7'—Fe169.7 (10)
C6—Fe1—C3157.8 (4)C8'—C7'—Fe168.9 (10)
C9—Fe1—C3122.9 (3)C6'—C7'—H7'A125.9
C10—Fe1—C3159.8 (4)C8'—C7'—H7'A125.9
C8—Fe1—C3106.9 (2)Fe1—C7'—H7'A125.9
C1—Fe1—C368.64 (7)C9'—C8'—C7'107.6 (5)
C5—Fe1—C368.11 (7)C9'—C8'—Fe172.3 (9)
C7—Fe1—C3121.8 (3)C7'—C8'—Fe171.0 (10)
C2—Fe1—C340.65 (7)C9'—C8'—H8'A126.1
C4—Fe1—C340.40 (7)C7'—C8'—H8'A126.1
C6—Fe1—C10'58.1 (4)Fe1—C8'—H8'A126.1
C9—Fe1—C10'23.1 (3)C8'—C9'—C10'107.9 (6)
C10—Fe1—C10'20.5 (2)C8'—C9'—Fe168.0 (9)
C8—Fe1—C10'59.7 (5)C10'—C9'—Fe167.9 (10)
C1—Fe1—C10'137.5 (6)C8'—C9'—H9'A126.0
C5—Fe1—C10'110.0 (5)C10'—C9'—H9'A126.0
C7—Fe1—C10'74.9 (5)Fe1—C9'—H9'A126.0
C2—Fe1—C10'178.0 (6)C6'—C10'—C9'108.0 (6)
C4—Fe1—C10'111.1 (4)C6'—C10'—Fe170.7 (12)
C3—Fe1—C10'139.7 (4)C9'—C10'—Fe172.2 (10)
C6—Fe1—C8'54.2 (6)C6'—C10'—H10B125.9
C9—Fe1—C8'54.7 (7)C9'—C10'—H10B125.9
C10—Fe1—C8'68.5 (4)Fe1—C10'—H10B125.9
C8—Fe1—C8'20.9 (8)N1—C11—C1112.68 (14)
C1—Fe1—C8'140.0 (9)N1—C11—H11A109.1
C5—Fe1—C8'177.7 (4)C1—C11—H11A109.1
C7—Fe1—C8'20.2 (8)N1—C11—H11B109.1
C2—Fe1—C8'114.0 (6)C1—C11—H11B109.1
C4—Fe1—C8'140.9 (8)H11A—C11—H11B107.8
C3—Fe1—C8'114.1 (5)N1—C12—H12A109.5
C10'—Fe1—C8'67.9 (5)N1—C12—H12B109.5
C13—N1—C12110.91 (14)H12A—C12—H12B109.5
C13—N1—C11111.59 (13)N1—C12—H12C109.5
C12—N1—C11109.34 (14)H12A—C12—H12C109.5
C2—C1—C5107.18 (15)H12B—C12—H12C109.5
C2—C1—C11126.48 (16)N1—C13—C14114.25 (14)
C5—C1—C11126.32 (16)N1—C13—H13A108.7
C2—C1—Fe169.90 (10)C14—C13—H13A108.7
C5—C1—Fe169.68 (10)N1—C13—H13B108.7
C11—C1—Fe1126.85 (12)C14—C13—H13B108.7
C1—C2—C3108.55 (16)H13A—C13—H13B107.6
C1—C2—Fe169.50 (9)C19—C14—C15117.75 (16)
C3—C2—Fe169.80 (10)C19—C14—C13122.20 (15)
C1—C2—H2125.7C15—C14—C13119.91 (16)
C3—C2—H2125.7C16—C15—C14121.12 (17)
Fe1—C2—H2125.7C16—C15—H15119.4
C4—C3—C2107.72 (16)C14—C15—H15119.4
C4—C3—Fe169.80 (11)C15—C16—C17121.34 (17)
C2—C3—Fe169.55 (10)C15—C16—H16119.3
C4—C3—H3126.1C17—C16—H16119.3
C2—C3—H3126.1C16—C17—C18117.34 (17)
Fe1—C3—H3126.1C16—C17—C20121.20 (17)
C5—C4—C3108.27 (15)C18—C17—C20121.46 (18)
C5—C4—Fe169.64 (10)C19—C18—C17121.35 (18)
C3—C4—Fe169.81 (10)C19—C18—H18119.3
C5—C4—H4125.9C17—C18—H18119.3
C3—C4—H4125.9C14—C19—C18121.10 (17)
Fe1—C4—H4125.9C14—C19—H19119.4
C4—C5—C1108.27 (16)C18—C19—H19119.4
C4—C5—Fe169.95 (10)C17—C20—H20A109.5
C1—C5—Fe169.36 (10)C17—C20—H20B109.5
C4—C5—H5125.9H20A—C20—H20B109.5
C1—C5—H5125.9C17—C20—H20C109.5
Fe1—C5—H5125.9H20A—C20—H20C109.5
C10—C6—C7108.4 (4)H20B—C20—H20C109.5
C10—C6—Fe169.8 (3)
C6—Fe1—C1—C2119.5 (4)C7—C8—C9—C100.0 (10)
C9—Fe1—C1—C2165.8 (6)Fe1—C8—C9—C1059.7 (4)
C10—Fe1—C1—C2161.1 (4)C7—C8—C9—Fe159.7 (8)
C8—Fe1—C1—C244.6 (5)C6—Fe1—C9—C881.5 (4)
C5—Fe1—C1—C2118.09 (14)C10—Fe1—C9—C8118.8 (5)
C7—Fe1—C1—C277.7 (4)C1—Fe1—C9—C8163.3 (3)
C4—Fe1—C1—C280.84 (11)C5—Fe1—C9—C8161.1 (4)
C3—Fe1—C1—C237.30 (10)C7—Fe1—C9—C837.9 (4)
C10'—Fe1—C1—C2179.1 (5)C2—Fe1—C9—C842.7 (8)
C8'—Fe1—C1—C265.2 (8)C4—Fe1—C9—C8119.1 (5)
C6—Fe1—C1—C5122.4 (4)C3—Fe1—C9—C876.9 (5)
C9—Fe1—C1—C547.8 (7)C10'—Fe1—C9—C8140.0 (12)
C10—Fe1—C1—C580.8 (4)C8'—Fe1—C9—C821.0 (8)
C8—Fe1—C1—C5162.7 (5)C6—Fe1—C9—C1037.3 (3)
C7—Fe1—C1—C5164.2 (3)C8—Fe1—C9—C10118.8 (5)
C2—Fe1—C1—C5118.09 (14)C1—Fe1—C9—C1044.4 (6)
C4—Fe1—C1—C537.26 (11)C5—Fe1—C9—C1080.1 (4)
C3—Fe1—C1—C580.79 (11)C7—Fe1—C9—C1081.0 (3)
C10'—Fe1—C1—C561.0 (6)C2—Fe1—C9—C10161.5 (6)
C8'—Fe1—C1—C5176.7 (8)C4—Fe1—C9—C10122.1 (4)
C6—Fe1—C1—C111.6 (4)C3—Fe1—C9—C10164.2 (4)
C9—Fe1—C1—C1173.0 (7)C10'—Fe1—C9—C1021.2 (11)
C10—Fe1—C1—C1140.0 (4)C8'—Fe1—C9—C1097.8 (8)
C8—Fe1—C1—C1176.5 (6)C7—C6—C10—C91.3 (8)
C5—Fe1—C1—C11120.79 (19)Fe1—C6—C10—C959.0 (4)
C7—Fe1—C1—C1143.4 (4)C7—C6—C10—Fe160.3 (6)
C2—Fe1—C1—C11121.12 (19)C8—C9—C10—C60.8 (7)
C4—Fe1—C1—C11158.05 (17)Fe1—C9—C10—C659.0 (4)
C3—Fe1—C1—C11158.42 (17)C8—C9—C10—Fe159.8 (5)
C10'—Fe1—C1—C1159.8 (6)C9—Fe1—C10—C6119.8 (4)
C8'—Fe1—C1—C1155.9 (8)C8—Fe1—C10—C682.0 (3)
C5—C1—C2—C30.94 (19)C1—Fe1—C10—C677.1 (4)
C11—C1—C2—C3179.38 (16)C5—Fe1—C10—C6120.4 (4)
Fe1—C1—C2—C359.05 (12)C7—Fe1—C10—C637.7 (3)
C5—C1—C2—Fe159.99 (11)C2—Fe1—C10—C641.6 (5)
C11—C1—C2—Fe1121.57 (17)C4—Fe1—C10—C6162.7 (3)
C6—Fe1—C2—C178.8 (3)C3—Fe1—C10—C6161.1 (4)
C9—Fe1—C2—C1166.5 (4)C10'—Fe1—C10—C6143.7 (14)
C10—Fe1—C2—C148.2 (5)C8'—Fe1—C10—C659.5 (9)
C8—Fe1—C2—C1162.1 (3)C6—Fe1—C10—C9119.8 (4)
C5—Fe1—C2—C138.54 (10)C8—Fe1—C10—C937.8 (3)
C7—Fe1—C2—C1120.3 (3)C1—Fe1—C10—C9163.0 (3)
C4—Fe1—C2—C182.25 (11)C5—Fe1—C10—C9119.8 (4)
C3—Fe1—C2—C1119.96 (15)C7—Fe1—C10—C982.1 (3)
C10'—Fe1—C2—C118 (12)C2—Fe1—C10—C9161.4 (4)
C8'—Fe1—C2—C1140.3 (10)C4—Fe1—C10—C977.5 (4)
C6—Fe1—C2—C3161.2 (3)C3—Fe1—C10—C941.3 (6)
C9—Fe1—C2—C346.5 (5)C10'—Fe1—C10—C923.9 (13)
C10—Fe1—C2—C3168.2 (4)C8'—Fe1—C10—C960.3 (9)
C8—Fe1—C2—C377.9 (3)C6—Fe1—C6'—C10'132.2 (18)
C1—Fe1—C2—C3119.96 (15)C9—Fe1—C6'—C10'20.4 (9)
C5—Fe1—C2—C381.42 (12)C10—Fe1—C6'—C10'6.7 (8)
C7—Fe1—C2—C3119.8 (3)C8—Fe1—C6'—C10'61.0 (10)
C4—Fe1—C2—C337.71 (11)C1—Fe1—C6'—C10'141.2 (11)
C10'—Fe1—C2—C3102 (12)C5—Fe1—C6'—C10'97.4 (12)
C8'—Fe1—C2—C399.7 (10)C7—Fe1—C6'—C10'102.7 (11)
C1—C2—C3—C40.7 (2)C2—Fe1—C6'—C10'177.0 (8)
Fe1—C2—C3—C459.59 (13)C4—Fe1—C6'—C10'60.9 (14)
C1—C2—C3—Fe158.87 (12)C3—Fe1—C6'—C10'82 (14)
C6—Fe1—C3—C4165.1 (4)C8'—Fe1—C6'—C10'81.8 (9)
C9—Fe1—C3—C479.4 (3)C6—Fe1—C6'—C7'13.2 (12)
C10—Fe1—C3—C448.7 (5)C9—Fe1—C6'—C7'98.6 (10)
C8—Fe1—C3—C4120.8 (3)C10—Fe1—C6'—C7'125.7 (16)
C1—Fe1—C3—C481.65 (12)C8—Fe1—C6'—C7'58.1 (9)
C5—Fe1—C3—C437.44 (11)C1—Fe1—C6'—C7'99.8 (11)
C7—Fe1—C3—C4163.0 (3)C5—Fe1—C6'—C7'143.6 (11)
C2—Fe1—C3—C4118.91 (16)C7—Fe1—C6'—C7'16.3 (9)
C10'—Fe1—C3—C458.0 (8)C2—Fe1—C6'—C7'64.0 (11)
C8'—Fe1—C3—C4141.8 (10)C4—Fe1—C6'—C7'179.9 (10)
C6—Fe1—C3—C246.2 (4)C3—Fe1—C6'—C7'159 (13)
C9—Fe1—C3—C2161.7 (3)C10'—Fe1—C6'—C7'119.0 (12)
C10—Fe1—C3—C2167.6 (4)C8'—Fe1—C6'—C7'37.2 (7)
C8—Fe1—C3—C2120.3 (3)C10'—C6'—C7'—C8'1 (3)
C1—Fe1—C3—C237.26 (10)Fe1—C6'—C7'—C8'58.3 (15)
C5—Fe1—C3—C281.47 (12)C10'—C6'—C7'—Fe159.3 (18)
C7—Fe1—C3—C278.1 (3)C6—Fe1—C7'—C6'17.7 (14)
C4—Fe1—C3—C2118.91 (16)C9—Fe1—C7'—C6'62.1 (7)
C10'—Fe1—C3—C2176.9 (8)C10—Fe1—C7'—C6'19.9 (6)
C8'—Fe1—C3—C299.3 (10)C8—Fe1—C7'—C6'105.1 (9)
C2—C3—C4—C50.2 (2)C1—Fe1—C7'—C6'96.3 (10)
Fe1—C3—C4—C559.21 (13)C5—Fe1—C7'—C6'57.3 (12)
C2—C3—C4—Fe159.44 (12)C7—Fe1—C7'—C6'142.6 (17)
C6—Fe1—C4—C543.7 (7)C2—Fe1—C7'—C6'140.5 (9)
C9—Fe1—C4—C5120.8 (4)C4—Fe1—C7'—C6'1 (17)
C10—Fe1—C4—C578.8 (4)C3—Fe1—C7'—C6'179.0 (6)
C8—Fe1—C4—C5163.2 (3)C10'—Fe1—C7'—C6'37.5 (7)
C1—Fe1—C4—C537.75 (10)C8'—Fe1—C7'—C6'119.9 (11)
C7—Fe1—C4—C5161.4 (5)C6—Fe1—C7'—C8'138 (2)
C2—Fe1—C4—C581.59 (12)C9—Fe1—C7'—C8'57.8 (9)
C3—Fe1—C4—C5119.53 (15)C10—Fe1—C7'—C8'100.0 (8)
C10'—Fe1—C4—C596.5 (6)C8—Fe1—C7'—C8'14.8 (9)
C8'—Fe1—C4—C5177.0 (10)C1—Fe1—C7'—C8'143.8 (11)
C6—Fe1—C4—C3163.2 (7)C5—Fe1—C7'—C8'177.1 (11)
C9—Fe1—C4—C3119.6 (4)C7—Fe1—C7'—C8'22.7 (15)
C10—Fe1—C4—C3161.6 (4)C2—Fe1—C7'—C8'99.7 (11)
C8—Fe1—C4—C377.3 (3)C4—Fe1—C7'—C8'119 (17)
C1—Fe1—C4—C381.78 (11)C3—Fe1—C7'—C8'61.2 (11)
C5—Fe1—C4—C3119.53 (15)C10'—Fe1—C7'—C8'82.3 (8)
C7—Fe1—C4—C341.8 (6)C6'—C7'—C8'—C9'5 (2)
C2—Fe1—C4—C337.94 (11)Fe1—C7'—C8'—C9'63.4 (13)
C10'—Fe1—C4—C3144.0 (6)C6'—C7'—C8'—Fe158.8 (15)
C8'—Fe1—C4—C363.5 (10)C6—Fe1—C8'—C9'101.9 (8)
C3—C4—C5—C10.4 (2)C9—Fe1—C8'—C9'14.4 (6)
Fe1—C4—C5—C158.96 (12)C10—Fe1—C8'—C9'58.3 (7)
C3—C4—C5—Fe159.32 (13)C8—Fe1—C8'—C9'26.2 (12)
C2—C1—C5—C40.80 (19)C1—Fe1—C8'—C9'175.1 (7)
C11—C1—C5—C4179.24 (16)C5—Fe1—C8'—C9'62 (25)
Fe1—C1—C5—C459.33 (12)C7—Fe1—C8'—C9'143.0 (17)
C2—C1—C5—Fe160.13 (12)C2—Fe1—C8'—C9'144.7 (8)
C11—C1—C5—Fe1121.43 (17)C4—Fe1—C8'—C9'60.5 (9)
C6—Fe1—C5—C4163.7 (4)C3—Fe1—C8'—C9'99.9 (8)
C9—Fe1—C5—C478.4 (4)C10'—Fe1—C8'—C9'36.2 (6)
C10—Fe1—C5—C4121.2 (5)C6—Fe1—C8'—C7'14.5 (7)
C8—Fe1—C5—C442.6 (6)C9—Fe1—C8'—C7'102.1 (8)
C1—Fe1—C5—C4119.61 (15)C10—Fe1—C8'—C7'58.2 (7)
C7—Fe1—C5—C4160.3 (7)C8—Fe1—C8'—C7'142.7 (18)
C2—Fe1—C5—C481.39 (12)C1—Fe1—C8'—C7'58.6 (11)
C3—Fe1—C5—C437.42 (11)C5—Fe1—C8'—C7'55 (25)
C10'—Fe1—C5—C499.4 (5)C7—Fe1—C8'—C7'26.5 (12)
C8'—Fe1—C5—C4125 (24)C2—Fe1—C8'—C7'98.9 (10)
C6—Fe1—C5—C176.7 (4)C4—Fe1—C8'—C7'177.0 (7)
C9—Fe1—C5—C1162.0 (4)C3—Fe1—C8'—C7'143.6 (9)
C10—Fe1—C5—C1119.2 (5)C10'—Fe1—C8'—C7'80.3 (7)
C8—Fe1—C5—C1162.3 (6)C7'—C8'—C9'—C10'6 (2)
C7—Fe1—C5—C140.7 (7)Fe1—C8'—C9'—C10'56.2 (14)
C2—Fe1—C5—C138.22 (10)C7'—C8'—C9'—Fe162.6 (14)
C4—Fe1—C5—C1119.61 (15)C6—Fe1—C9'—C8'57.6 (7)
C3—Fe1—C5—C182.18 (11)C9—Fe1—C9'—C8'139.5 (18)
C10'—Fe1—C5—C1141.0 (5)C10—Fe1—C9'—C8'100.2 (8)
C8'—Fe1—C5—C1116 (24)C8—Fe1—C9'—C8'24.2 (14)
C9—Fe1—C6—C1037.4 (3)C1—Fe1—C9'—C8'88 (16)
C8—Fe1—C6—C1081.0 (3)C5—Fe1—C9'—C8'176.9 (9)
C1—Fe1—C6—C10121.5 (4)C7—Fe1—C9'—C8'14.3 (8)
C5—Fe1—C6—C1079.6 (4)C2—Fe1—C9'—C8'59.3 (9)
C7—Fe1—C6—C10119.0 (5)C4—Fe1—C9'—C8'143.2 (9)
C2—Fe1—C6—C10163.5 (4)C3—Fe1—C9'—C8'98.9 (9)
C4—Fe1—C6—C1046.9 (6)C10'—Fe1—C9'—C8'121.5 (10)
C3—Fe1—C6—C10162.8 (5)C6—Fe1—C9'—C10'63.9 (7)
C10'—Fe1—C6—C1014.2 (5)C9—Fe1—C9'—C10'18.1 (13)
C8'—Fe1—C6—C1098.6 (9)C10—Fe1—C9'—C10'21.3 (6)
C9—Fe1—C6—C781.7 (4)C8—Fe1—C9'—C10'145.7 (17)
C10—Fe1—C6—C7119.0 (5)C1—Fe1—C9'—C10'34 (16)
C8—Fe1—C6—C738.0 (4)C5—Fe1—C9'—C10'55.4 (11)
C1—Fe1—C6—C7119.5 (4)C7—Fe1—C9'—C10'107.1 (8)
C5—Fe1—C6—C7161.4 (4)C2—Fe1—C9'—C10'179.2 (6)
C2—Fe1—C6—C777.5 (5)C4—Fe1—C9'—C10'95.3 (9)
C4—Fe1—C6—C7165.9 (4)C3—Fe1—C9'—C10'139.7 (8)
C3—Fe1—C6—C743.7 (7)C8'—Fe1—C9'—C10'121.5 (10)
C10'—Fe1—C6—C7104.9 (6)C7'—C6'—C10'—C9'3 (3)
C8'—Fe1—C6—C720.4 (9)Fe1—C6'—C10'—C9'63.0 (16)
C10—C6—C7—C81.3 (11)C7'—C6'—C10'—Fe160.0 (17)
Fe1—C6—C7—C858.6 (7)C8'—C9'—C10'—C6'6 (3)
C10—C6—C7—Fe159.9 (4)Fe1—C9'—C10'—C6'62.1 (17)
C9—Fe1—C7—C681.6 (4)C8'—C9'—C10'—Fe156.2 (14)
C10—Fe1—C7—C637.8 (4)C6—Fe1—C10'—C6'20.5 (8)
C8—Fe1—C7—C6119.1 (7)C9—Fe1—C10'—C6'131.4 (19)
C1—Fe1—C7—C678.9 (5)C10—Fe1—C10'—C6'6.4 (8)
C5—Fe1—C7—C648.6 (8)C8—Fe1—C10'—C6'102.6 (11)
C2—Fe1—C7—C6120.4 (5)C1—Fe1—C10'—C6'60.3 (14)
C4—Fe1—C7—C6167.3 (5)C5—Fe1—C10'—C6'97.9 (12)
C3—Fe1—C7—C6162.1 (5)C7—Fe1—C10'—C6'61.1 (10)
C10'—Fe1—C7—C658.2 (5)C2—Fe1—C10'—C6'77 (12)
C8'—Fe1—C7—C6124.9 (15)C4—Fe1—C10'—C6'141.1 (11)
C6—Fe1—C7—C8119.1 (7)C3—Fe1—C10'—C6'177.2 (7)
C9—Fe1—C7—C837.5 (4)C8'—Fe1—C10'—C6'81.1 (9)
C10—Fe1—C7—C881.3 (5)C6—Fe1—C10'—C9'96.6 (9)
C1—Fe1—C7—C8162.1 (5)C9—Fe1—C10'—C9'14.3 (13)
C5—Fe1—C7—C8167.6 (3)C10—Fe1—C10'—C9'123.6 (15)
C2—Fe1—C7—C8120.5 (6)C8—Fe1—C10'—C9'14.6 (9)
C4—Fe1—C7—C848.3 (9)C1—Fe1—C10'—C9'177.4 (10)
C3—Fe1—C7—C878.8 (6)C5—Fe1—C10'—C9'145.0 (10)
C10'—Fe1—C7—C860.9 (5)C7—Fe1—C10'—C9'56.1 (9)
C8'—Fe1—C7—C85.8 (13)C2—Fe1—C10'—C9'166 (11)
C6—C7—C8—C90.8 (12)C4—Fe1—C10'—C9'101.8 (10)
Fe1—C7—C8—C959.4 (6)C3—Fe1—C10'—C9'65.7 (10)
C6—C7—C8—Fe158.6 (7)C8'—Fe1—C10'—C9'36.1 (6)
C6—Fe1—C8—C981.7 (4)C13—N1—C11—C159.46 (19)
C10—Fe1—C8—C937.9 (4)C12—N1—C11—C1177.47 (15)
C1—Fe1—C8—C9164.2 (5)C2—C1—C11—N167.2 (2)
C5—Fe1—C8—C948.5 (8)C5—C1—C11—N1110.91 (19)
C7—Fe1—C8—C9119.3 (7)Fe1—C1—C11—N1158.38 (12)
C2—Fe1—C8—C9163.0 (5)C12—N1—C13—C1471.31 (19)
C4—Fe1—C8—C979.9 (5)C11—N1—C13—C14166.52 (14)
C3—Fe1—C8—C9121.3 (5)N1—C13—C14—C1926.5 (2)
C10'—Fe1—C8—C917.0 (4)N1—C13—C14—C15157.89 (15)
C8'—Fe1—C8—C9125.0 (15)C19—C14—C15—C160.7 (3)
C6—Fe1—C8—C737.6 (5)C13—C14—C15—C16175.13 (17)
C9—Fe1—C8—C7119.3 (7)C14—C15—C16—C170.5 (3)
C10—Fe1—C8—C781.4 (5)C15—C16—C17—C180.2 (3)
C1—Fe1—C8—C744.9 (9)C15—C16—C17—C20179.57 (19)
C5—Fe1—C8—C7167.9 (4)C16—C17—C18—C190.7 (3)
C2—Fe1—C8—C777.6 (6)C20—C17—C18—C19179.95 (18)
C4—Fe1—C8—C7160.7 (5)C15—C14—C19—C180.2 (3)
C3—Fe1—C8—C7119.4 (6)C13—C14—C19—C18175.52 (16)
C10'—Fe1—C8—C7102.4 (6)C17—C18—C19—C140.5 (3)
C8'—Fe1—C8—C75.6 (12)

Experimental details

Crystal data
Chemical formula[Fe(C5H5)(C15H18N)]
Mr333.24
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)14.8570 (14), 5.9690 (5), 19.3667 (18)
β (°) 102.530 (1)
V3)1676.6 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.90
Crystal size (mm)0.38 × 0.26 × 0.20
Data collection
DiffractometerBruker APEX-II CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.635, 0.836
No. of measured, independent and
observed [I > 2σ(I)] reflections
8678, 2950, 2436
Rint0.017
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.027, 0.078, 1.06
No. of reflections2950
No. of parameters246
No. of restraints20
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.18, 0.31

Computer programs: SMART (Bruker, 2003), SMART, SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1998), SHELXTL.

Selected geometric parameters (Å, º) top
Fe1—C12.0334 (17)N1—C111.462 (2)
N1—C131.453 (2)C1—C21.413 (2)
N1—C121.460 (2)C13—C141.509 (2)
C13—N1—C12110.91 (14)N1—C11—C1112.68 (14)
C13—N1—C11111.59 (13)N1—C13—C14114.25 (14)
C12—N1—C11109.34 (14)
C12—N1—C11—C1177.47 (15)C11—N1—C13—C14166.52 (14)
C12—N1—C13—C1471.31 (19)
 

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