Literature DB >> 23125597

3-(Ferrocen-1-ylcarbon-yl)-1-methyl-4-(4-methyl-phen-yl)spiro-[pyrrolidine-2,11'-indeno-[1,2-b]quinoxaline].

B Vijayakumar1, D Gavaskar, T Srinivasan, R Raghunathan, D Velmurugan.   

Abstract

In the title compound, [Fe(C(5)H(5))(C(32)H(26)N(3)O)], the pyrrolidine ring adopts a twist conformation. The indeno-quinoxaline ring system [86.44 (5)°], the methyl-phenyl ring [86.06 (7)°] and the ferrocene rings [82.00 (7) and 83.95 (9)°] are almost perpendicular to the pyrrolidine ring. The two cyclopentadienyl rings adopt an eclipsed conformation. The crystal structure features C-H⋯N inter-actions.

Entities:  

Year:  2012        PMID： 23125597      PMCID： PMC3470153          DOI： 10.1107/S1600536812036951

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


Related literature

For the biological activity of ferrocene derivatives, see: Jaouen et al. (2004 ▶); Biot et al. (2004 ▶); Fouda et al. (2007 ▶). For related structures, see: Satis Kumar et al.(2007 ▶); Kamala et al. (2009 ▶); Gunasekaran et al. (2010 ▶); For puckering and asymmetry parameters, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶).

Experimental

Crystal data

[Fe(C5H5)(C32H26N3O)] M = 589.50 Monoclinic, a = 11.5966 (3) Å b = 11.8658 (3) Å c = 20.9383 (6) Å β = 90.616 (2)° V = 2881.01 (13) Å3 Z = 4 Mo Kα radiation μ = 0.56 mm−1 T = 293 K 0.2 × 0.2 × 0.2 mm

Data collection

Bruker SMART APEXII area-detector diffractometer 26509 measured reflections 7145 independent reflections 5247 reflections with I > 2σ(I) R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.037 wR(F 2) = 0.110 S = 1.02 7145 reflections 381 parameters H-atom parameters constrained Δρmax = 0.26 e Å−3 Δρmin = −0.31 e Å−3 Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812036951/bt6825sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812036951/bt6825Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536812036951/bt6825Isup4.mol Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Fe(C5H5)(C32H26N3O)]F(000) = 1232
Mr = 589.50Dx = 1.359 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 7145 reflections
a = 11.5966 (3) Åθ = 2.0–28.3°
b = 11.8658 (3) ŵ = 0.56 mm−1
c = 20.9383 (6) ÅT = 293 K
β = 90.616 (2)°Block, brown
V = 2881.01 (13) Å30.2 × 0.2 × 0.2 mm
Z = 4
Bruker SMART APEXII area-detector diffractometer5247 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.026
Graphite monochromatorθmax = 28.3°, θmin = 2.0°
ω and φ scansh = −14→15
26509 measured reflectionsk = −15→14
7145 independent reflectionsl = −27→25
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0573P)2 + 0.5923P] where P = (Fo2 + 2Fc2)/3
7145 reflections(Δ/σ)max = 0.023
381 parametersΔρmax = 0.26 e Å−3
0 restraintsΔρmin = −0.31 e Å−3
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.
xyzUiso*/Ueq
C10.29739 (19)0.35976 (18)−0.10411 (9)0.0570 (5)
H10.23310.4050−0.09760.068*
C20.3437 (2)0.3508 (2)−0.16349 (10)0.0716 (7)
H20.31100.3904−0.19750.086*
C30.4399 (2)0.2825 (2)−0.17355 (11)0.0776 (8)
H30.47190.2789−0.21410.093*
C40.4876 (2)0.2215 (2)−0.12547 (11)0.0718 (7)
H40.55020.1747−0.13330.086*
C50.44203 (16)0.22899 (17)−0.06319 (9)0.0527 (5)
C60.34719 (15)0.30038 (15)−0.05269 (8)0.0461 (4)
C70.35581 (13)0.26030 (14)0.05261 (8)0.0378 (3)
C80.45054 (14)0.18715 (15)0.04184 (9)0.0447 (4)
C90.49029 (15)0.14277 (15)0.10323 (9)0.0473 (4)
C100.42069 (14)0.18700 (14)0.15109 (8)0.0412 (4)
C110.32625 (13)0.26329 (13)0.12383 (7)0.0357 (3)
C120.44572 (16)0.16378 (16)0.21433 (9)0.0524 (4)
H120.40150.19470.24670.063*
C130.53779 (19)0.09358 (19)0.22876 (12)0.0669 (6)
H130.55440.07640.27120.080*
C140.6054 (2)0.0487 (2)0.18112 (13)0.0735 (7)
H140.66660.00160.19190.088*
C150.58319 (18)0.07298 (18)0.11806 (12)0.0659 (6)
H150.62920.04350.08600.079*
C160.19757 (12)0.22576 (13)0.13323 (7)0.0335 (3)
H160.16610.20270.09160.040*
C170.13242 (14)0.33248 (14)0.15504 (8)0.0384 (4)
H170.11920.32680.20110.046*
C180.21749 (15)0.42714 (14)0.14355 (8)0.0414 (4)
H18A0.21110.45520.10010.050*
H18B0.20530.48900.17300.050*
C190.42792 (17)0.44471 (16)0.14190 (10)0.0530 (5)
H19A0.42620.46740.09790.080*
H19B0.49740.40320.15050.080*
H19C0.42570.51030.16870.080*
C200.01671 (14)0.34623 (14)0.12153 (8)0.0395 (4)
C21−0.08575 (16)0.34224 (17)0.15446 (9)0.0530 (5)
H21−0.08410.33380.19860.064*
C22−0.19103 (16)0.35058 (18)0.12277 (11)0.0594 (5)
H22−0.25870.34570.14610.071*
C23−0.19783 (15)0.36583 (15)0.05778 (10)0.0501 (4)
C24−0.09542 (16)0.37090 (16)0.02483 (9)0.0500 (4)
H24−0.09740.3811−0.01920.060*
C250.01009 (15)0.36115 (15)0.05584 (8)0.0457 (4)
H250.07760.36470.03230.055*
C260.18900 (13)0.12623 (14)0.17858 (7)0.0352 (3)
C270.20428 (13)0.01427 (14)0.15034 (7)0.0357 (3)
C280.20015 (15)−0.08985 (14)0.18424 (9)0.0429 (4)
H280.1963−0.09820.22830.051*
C290.20304 (17)−0.17801 (16)0.13901 (10)0.0535 (5)
H290.2013−0.25470.14820.064*
C300.20898 (17)−0.13008 (16)0.07734 (9)0.0527 (5)
H300.2115−0.16990.03910.063*
C310.21043 (14)−0.01244 (14)0.08348 (8)0.0408 (4)
H310.21460.03920.05020.049*
C32−0.07832 (18)0.0154 (3)0.14632 (14)0.0808 (8)
H32−0.07820.08580.16590.097*
C33−0.07821 (18)−0.0055 (2)0.08054 (12)0.0733 (7)
H33−0.07790.04870.04850.088*
C34−0.0786 (2)−0.1200 (3)0.07176 (14)0.0866 (8)
H34−0.0791−0.15670.03250.104*
C35−0.0781 (2)−0.1716 (3)0.1306 (2)0.0998 (11)
H35−0.0775−0.24900.13780.120*
C36−0.0786 (2)−0.0890 (4)0.17706 (14)0.0946 (10)
H36−0.0790−0.10080.22100.114*
C37−0.31185 (17)0.3780 (2)0.02292 (12)0.0678 (6)
H37A−0.37130.34180.04700.102*
H37B−0.30680.3433−0.01840.102*
H37C−0.32990.45650.01790.102*
N10.30156 (12)0.31494 (12)0.00747 (6)0.0426 (3)
N20.49441 (14)0.16877 (15)−0.01466 (8)0.0561 (4)
N30.32874 (11)0.37402 (11)0.15487 (6)0.0384 (3)
O10.17339 (11)0.13915 (11)0.23535 (5)0.0502 (3)
Fe10.06387 (2)−0.07469 (2)0.123016 (11)0.04181 (9)
U11U22U33U12U13U23
C10.0695 (13)0.0608 (12)0.0408 (10)−0.0229 (10)0.0043 (9)−0.0020 (9)
C20.0903 (17)0.0848 (17)0.0399 (11)−0.0422 (14)0.0044 (10)−0.0026 (11)
C30.0872 (17)0.103 (2)0.0433 (12)−0.0423 (15)0.0236 (11)−0.0244 (13)
C40.0661 (14)0.0919 (18)0.0579 (14)−0.0252 (13)0.0249 (11)−0.0307 (13)
C50.0510 (11)0.0600 (12)0.0476 (10)−0.0217 (9)0.0151 (8)−0.0189 (9)
C60.0517 (10)0.0489 (10)0.0380 (9)−0.0218 (8)0.0080 (7)−0.0086 (7)
C70.0373 (8)0.0370 (8)0.0393 (9)−0.0097 (7)0.0073 (6)−0.0064 (7)
C80.0378 (9)0.0427 (9)0.0537 (10)−0.0075 (7)0.0089 (7)−0.0114 (8)
C90.0369 (9)0.0424 (10)0.0628 (12)−0.0022 (7)0.0026 (8)−0.0088 (8)
C100.0355 (8)0.0385 (9)0.0496 (10)−0.0034 (7)−0.0016 (7)−0.0036 (7)
C110.0356 (8)0.0368 (8)0.0348 (8)−0.0032 (6)0.0010 (6)−0.0023 (6)
C120.0497 (10)0.0536 (11)0.0538 (11)0.0018 (8)−0.0090 (8)−0.0014 (9)
C130.0622 (13)0.0615 (13)0.0765 (15)0.0061 (10)−0.0222 (11)0.0043 (11)
C140.0544 (13)0.0641 (14)0.1016 (19)0.0161 (11)−0.0182 (12)−0.0036 (13)
C150.0484 (11)0.0575 (13)0.0917 (18)0.0102 (9)0.0034 (11)−0.0122 (11)
C160.0339 (8)0.0361 (8)0.0305 (8)−0.0021 (6)0.0011 (6)−0.0018 (6)
C170.0409 (9)0.0408 (9)0.0335 (8)0.0033 (7)0.0032 (6)−0.0011 (7)
C180.0475 (9)0.0357 (9)0.0410 (9)0.0025 (7)−0.0014 (7)−0.0051 (7)
C190.0515 (11)0.0469 (10)0.0606 (12)−0.0133 (8)−0.0008 (9)−0.0063 (9)
C200.0394 (8)0.0360 (8)0.0432 (9)0.0020 (7)0.0048 (7)0.0002 (7)
C210.0468 (10)0.0617 (12)0.0506 (11)0.0095 (9)0.0104 (8)0.0096 (9)
C220.0385 (10)0.0653 (13)0.0747 (14)0.0055 (9)0.0139 (9)0.0093 (11)
C230.0394 (9)0.0400 (10)0.0709 (13)0.0003 (7)−0.0035 (8)−0.0021 (9)
C240.0492 (10)0.0511 (11)0.0497 (10)−0.0014 (8)−0.0039 (8)−0.0026 (8)
C250.0383 (9)0.0532 (11)0.0456 (10)−0.0015 (8)0.0033 (7)−0.0006 (8)
C260.0337 (8)0.0400 (9)0.0318 (8)−0.0031 (6)0.0002 (6)−0.0008 (6)
C270.0333 (8)0.0392 (9)0.0347 (8)−0.0015 (6)−0.0013 (6)0.0011 (6)
C280.0423 (9)0.0427 (9)0.0436 (9)0.0008 (7)−0.0034 (7)0.0065 (7)
C290.0602 (12)0.0362 (10)0.0641 (12)0.0060 (8)0.0006 (9)0.0032 (8)
C300.0615 (12)0.0460 (11)0.0508 (11)0.0047 (9)0.0035 (9)−0.0112 (8)
C310.0436 (9)0.0427 (9)0.0362 (8)0.0006 (7)0.0044 (7)0.0006 (7)
C320.0390 (11)0.099 (2)0.105 (2)0.0058 (12)0.0031 (12)−0.0299 (17)
C330.0480 (12)0.0911 (18)0.0804 (16)0.0039 (11)−0.0125 (11)0.0230 (14)
C340.0658 (15)0.100 (2)0.093 (2)−0.0099 (14)−0.0330 (14)−0.0246 (17)
C350.0642 (16)0.0845 (19)0.150 (3)−0.0357 (14)−0.0271 (18)0.036 (2)
C360.0426 (12)0.167 (3)0.0742 (17)−0.0171 (16)0.0051 (11)0.032 (2)
C370.0438 (11)0.0635 (13)0.0959 (17)0.0014 (10)−0.0121 (10)−0.0107 (12)
N10.0465 (8)0.0462 (8)0.0352 (7)−0.0094 (6)0.0064 (6)−0.0033 (6)
N20.0477 (9)0.0622 (10)0.0588 (10)−0.0089 (8)0.0153 (7)−0.0201 (8)
N30.0403 (7)0.0357 (7)0.0392 (7)−0.0039 (6)−0.0005 (6)−0.0054 (6)
O10.0692 (8)0.0498 (7)0.0319 (6)−0.0028 (6)0.0060 (5)−0.0001 (5)
Fe10.04165 (15)0.04181 (15)0.04185 (15)−0.00598 (10)−0.00464 (10)0.00020 (10)
C1—C21.364 (3)C20—C251.388 (2)
C1—C61.406 (3)C21—C221.387 (3)
C1—H10.9300C21—H210.9300
C2—C31.398 (4)C22—C231.374 (3)
C2—H20.9300C22—H220.9300
C3—C41.353 (4)C23—C241.381 (3)
C3—H30.9300C23—C371.510 (3)
C4—C51.415 (3)C24—C251.384 (2)
C4—H40.9300C24—H240.9300
C5—N21.378 (3)C25—H250.9300
C5—C61.407 (3)C26—O11.2140 (19)
C6—N11.382 (2)C26—C271.466 (2)
C7—N11.303 (2)C27—C281.426 (2)
C7—C81.420 (2)C27—C311.438 (2)
C7—C111.534 (2)C27—Fe12.0181 (15)
C8—N21.311 (2)C28—C291.412 (3)
C8—C91.459 (3)C28—Fe12.0321 (17)
C9—C151.391 (3)C28—H280.9300
C9—C101.396 (2)C29—C301.413 (3)
C10—C121.380 (2)C29—Fe12.0513 (19)
C10—C111.527 (2)C29—H290.9300
C11—N31.466 (2)C30—C311.402 (3)
C11—C161.572 (2)C30—Fe12.053 (2)
C12—C131.385 (3)C30—H300.9300
C12—H120.9300C31—Fe12.0372 (17)
C13—C141.382 (3)C31—H310.9300
C13—H130.9300C32—C331.400 (3)
C14—C151.373 (3)C32—C361.396 (4)
C14—H140.9300C32—Fe12.029 (2)
C15—H150.9300C32—H320.9300
C16—C261.519 (2)C33—C341.371 (4)
C16—C171.546 (2)C33—Fe12.037 (2)
C16—H160.9800C33—H330.9300
C17—C181.516 (2)C34—C351.375 (4)
C17—C201.516 (2)C34—Fe12.033 (2)
C17—H170.9800C34—H340.9300
C18—N31.453 (2)C35—C361.382 (5)
C18—H18A0.9700C35—Fe12.016 (2)
C18—H18B0.9700C35—H350.9300
C19—N31.452 (2)C36—Fe12.019 (2)
C19—H19A0.9600C36—H360.9300
C19—H19B0.9600C37—H37A0.9600
C19—H19C0.9600C37—H37B0.9600
C20—C211.381 (2)C37—H37C0.9600
C2—C1—C6119.8 (2)C30—C29—C28108.45 (16)
C2—C1—H1120.1C30—C29—Fe169.90 (11)
C6—C1—H1120.1C28—C29—Fe169.05 (10)
C1—C2—C3120.3 (2)C30—C29—H29125.8
C1—C2—H2119.8C28—C29—H29125.8
C3—C2—H2119.8Fe1—C29—H29126.9
C4—C3—C2121.2 (2)C31—C30—C29108.52 (16)
C4—C3—H3119.4C31—C30—Fe169.37 (10)
C2—C3—H3119.4C29—C30—Fe169.81 (11)
C3—C4—C5119.9 (2)C31—C30—H30125.7
C3—C4—H4120.0C29—C30—H30125.7
C5—C4—H4120.0Fe1—C30—H30126.7
N2—C5—C6122.42 (16)C30—C31—C27107.94 (15)
N2—C5—C4118.8 (2)C30—C31—Fe170.55 (11)
C6—C5—C4118.8 (2)C27—C31—Fe168.52 (9)
N1—C6—C1118.50 (18)C30—C31—H31126.0
N1—C6—C5121.66 (17)C27—C31—H31126.0
C1—C6—C5119.84 (17)Fe1—C31—H31126.5
N1—C7—C8123.88 (15)C33—C32—C36107.2 (3)
N1—C7—C11125.63 (15)C33—C32—Fe170.14 (13)
C8—C7—C11110.48 (15)C36—C32—Fe169.44 (15)
N2—C8—C7123.60 (18)C33—C32—H32126.4
N2—C8—C9127.79 (17)C36—C32—H32126.4
C7—C8—C9108.56 (15)Fe1—C32—H32125.6
C15—C9—C10121.06 (19)C34—C33—C32107.9 (2)
C15—C9—C8130.39 (19)C34—C33—Fe170.17 (13)
C10—C9—C8108.48 (15)C32—C33—Fe169.59 (13)
C12—C10—C9119.76 (17)C34—C33—H33126.0
C12—C10—C11128.28 (16)C32—C33—H33126.0
C9—C10—C11111.88 (15)Fe1—C33—H33125.8
N3—C11—C10110.80 (12)C33—C34—C35108.7 (3)
N3—C11—C7116.62 (13)C33—C34—Fe170.45 (13)
C10—C11—C7100.53 (13)C35—C34—Fe169.48 (14)
N3—C11—C16102.27 (12)C33—C34—H34125.6
C10—C11—C16117.61 (13)C35—C34—H34125.6
C7—C11—C16109.73 (12)Fe1—C34—H34126.0
C10—C12—C13118.9 (2)C34—C35—C36108.3 (3)
C10—C12—H12120.6C34—C35—Fe170.82 (15)
C13—C12—H12120.6C36—C35—Fe170.11 (14)
C14—C13—C12121.1 (2)C34—C35—H35125.8
C14—C13—H13119.5C36—C35—H35125.8
C12—C13—H13119.5Fe1—C35—H35124.8
C15—C14—C13120.8 (2)C35—C36—C32107.8 (3)
C15—C14—H14119.6C35—C36—Fe169.84 (16)
C13—C14—H14119.6C32—C36—Fe170.21 (14)
C14—C15—C9118.4 (2)C35—C36—H36126.1
C14—C15—H15120.8C32—C36—H36126.1
C9—C15—H15120.8Fe1—C36—H36125.4
C26—C16—C17114.62 (12)C23—C37—H37A109.5
C26—C16—C11111.53 (12)C23—C37—H37B109.5
C17—C16—C11105.82 (12)H37A—C37—H37B109.5
C26—C16—H16108.2C23—C37—H37C109.5
C17—C16—H16108.2H37A—C37—H37C109.5
C11—C16—H16108.2H37B—C37—H37C109.5
C18—C17—C20114.90 (14)C7—N1—C6114.35 (15)
C18—C17—C16103.84 (12)C8—N2—C5114.00 (17)
C20—C17—C16112.60 (13)C19—N3—C18115.01 (14)
C18—C17—H17108.4C19—N3—C11116.54 (13)
C20—C17—H17108.4C18—N3—C11107.65 (12)
C16—C17—H17108.4C35—Fe1—C27158.95 (12)
N3—C18—C17103.35 (13)C35—Fe1—C3640.05 (13)
N3—C18—H18A111.1C27—Fe1—C36123.19 (11)
C17—C18—H18A111.1C35—Fe1—C3267.39 (13)
N3—C18—H18B111.1C27—Fe1—C32108.14 (9)
C17—C18—H18B111.1C36—Fe1—C3240.35 (12)
H18A—C18—H18B109.1C35—Fe1—C3439.71 (12)
N3—C19—H19A109.5C27—Fe1—C34159.51 (11)
N3—C19—H19B109.5C36—Fe1—C3466.96 (12)
H19A—C19—H19B109.5C32—Fe1—C3466.95 (11)
N3—C19—H19C109.5C35—Fe1—C28122.02 (11)
H19A—C19—H19C109.5C27—Fe1—C2841.22 (6)
H19B—C19—H19C109.5C36—Fe1—C28105.92 (10)
C21—C20—C25117.41 (16)C32—Fe1—C28121.56 (9)
C21—C20—C17121.82 (15)C34—Fe1—C28158.70 (11)
C25—C20—C17120.75 (15)C35—Fe1—C3366.84 (11)
C20—C21—C22121.10 (18)C27—Fe1—C33124.02 (9)
C20—C21—H21119.5C36—Fe1—C3367.40 (11)
C22—C21—H21119.5C32—Fe1—C3340.27 (10)
C23—C22—C21121.60 (18)C34—Fe1—C3339.38 (11)
C23—C22—H22119.2C28—Fe1—C33158.62 (10)
C21—C22—H22119.2C35—Fe1—C31157.57 (13)
C22—C23—C24117.38 (17)C27—Fe1—C3141.54 (6)
C22—C23—C37122.12 (18)C36—Fe1—C31161.66 (13)
C24—C23—C37120.50 (19)C32—Fe1—C31126.18 (10)
C23—C24—C25121.52 (18)C34—Fe1—C31123.94 (11)
C23—C24—H24119.2C28—Fe1—C3169.01 (7)
C25—C24—H24119.2C33—Fe1—C31110.55 (9)
C24—C25—C20120.98 (17)C35—Fe1—C29106.73 (11)
C24—C25—H25119.5C27—Fe1—C2968.61 (7)
C20—C25—H25119.5C36—Fe1—C29120.34 (11)
O1—C26—C27121.96 (15)C32—Fe1—C29156.28 (11)
O1—C26—C16121.68 (14)C34—Fe1—C29124.16 (10)
C27—C26—C16116.33 (13)C28—Fe1—C2940.44 (7)
C28—C27—C31107.21 (14)C33—Fe1—C29160.65 (10)
C28—C27—C26125.44 (14)C31—Fe1—C2967.96 (7)
C31—C27—C26126.87 (14)C35—Fe1—C30121.88 (13)
C28—C27—Fe169.92 (9)C27—Fe1—C3068.69 (7)
C31—C27—Fe169.94 (9)C36—Fe1—C30156.05 (13)
C26—C27—Fe1119.20 (10)C32—Fe1—C30162.39 (11)
C29—C28—C27107.88 (16)C34—Fe1—C30109.57 (10)
C29—C28—Fe170.51 (10)C28—Fe1—C3068.26 (8)
C27—C28—Fe168.86 (9)C33—Fe1—C30126.09 (10)
C29—C28—H28126.1C31—Fe1—C3040.09 (7)
C27—C28—H28126.1C29—Fe1—C3040.29 (8)
Fe1—C28—H28126.1
C6—C1—C2—C30.3 (3)C26—C27—Fe1—C36−44.61 (18)
C1—C2—C3—C41.8 (3)C28—C27—Fe1—C32117.50 (13)
C2—C3—C4—C5−2.0 (3)C31—C27—Fe1—C32−124.53 (13)
C3—C4—C5—N2−177.95 (19)C26—C27—Fe1—C32−2.69 (16)
C3—C4—C5—C60.1 (3)C28—C27—Fe1—C34−170.0 (3)
C2—C1—C6—N1177.18 (17)C31—C27—Fe1—C34−52.0 (3)
C2—C1—C6—C5−2.2 (3)C26—C27—Fe1—C3469.9 (3)
N2—C5—C6—N10.6 (3)C31—C27—Fe1—C28117.96 (14)
C4—C5—C6—N1−177.38 (16)C26—C27—Fe1—C28−120.19 (16)
N2—C5—C6—C1179.95 (16)C28—C27—Fe1—C33159.12 (12)
C4—C5—C6—C12.0 (3)C31—C27—Fe1—C33−82.91 (13)
N1—C7—C8—N21.3 (3)C26—C27—Fe1—C3338.93 (16)
C11—C7—C8—N2−179.79 (15)C28—C27—Fe1—C31−117.96 (14)
N1—C7—C8—C9178.99 (15)C26—C27—Fe1—C31121.85 (16)
C11—C7—C8—C9−2.10 (18)C28—C27—Fe1—C29−37.51 (11)
N2—C8—C9—C151.2 (3)C31—C27—Fe1—C2980.46 (11)
C7—C8—C9—C15−176.42 (19)C26—C27—Fe1—C29−157.70 (14)
N2—C8—C9—C10178.05 (17)C28—C27—Fe1—C30−80.91 (11)
C7—C8—C9—C100.48 (19)C31—C27—Fe1—C3037.05 (10)
C15—C9—C10—C121.7 (3)C26—C27—Fe1—C30158.90 (14)
C8—C9—C10—C12−175.58 (16)C32—C36—Fe1—C35−118.5 (2)
C15—C9—C10—C11178.59 (16)C35—C36—Fe1—C27−162.74 (16)
C8—C9—C10—C111.34 (19)C32—C36—Fe1—C2778.74 (17)
C12—C10—C11—N350.2 (2)C35—C36—Fe1—C32118.5 (2)
C9—C10—C11—N3−126.35 (15)C35—C36—Fe1—C3437.51 (18)
C12—C10—C11—C7174.18 (17)C32—C36—Fe1—C34−81.01 (18)
C9—C10—C11—C7−2.42 (17)C35—C36—Fe1—C28−121.17 (17)
C12—C10—C11—C16−66.8 (2)C32—C36—Fe1—C28120.32 (16)
C9—C10—C11—C16116.57 (16)C35—C36—Fe1—C3380.39 (19)
N1—C7—C11—N3−58.6 (2)C32—C36—Fe1—C33−38.13 (16)
C8—C7—C11—N3122.49 (15)C35—C36—Fe1—C31167.7 (2)
N1—C7—C11—C10−178.43 (15)C32—C36—Fe1—C3149.2 (4)
C8—C7—C11—C102.68 (16)C35—C36—Fe1—C29−79.76 (19)
N1—C7—C11—C1657.0 (2)C32—C36—Fe1—C29161.73 (14)
C8—C7—C11—C16−121.89 (14)C35—C36—Fe1—C30−49.0 (3)
C9—C10—C12—C13−2.1 (3)C32—C36—Fe1—C30−167.52 (19)
C11—C10—C12—C13−178.46 (18)C33—C32—Fe1—C35−80.36 (18)
C10—C12—C13—C141.2 (3)C36—C32—Fe1—C3537.77 (17)
C12—C13—C14—C150.2 (4)C33—C32—Fe1—C27121.61 (15)
C13—C14—C15—C9−0.7 (3)C36—C32—Fe1—C27−120.26 (17)
C10—C9—C15—C14−0.2 (3)C33—C32—Fe1—C36−118.1 (2)
C8—C9—C15—C14176.3 (2)C33—C32—Fe1—C34−37.11 (16)
N3—C11—C16—C26−112.15 (13)C36—C32—Fe1—C3481.01 (19)
C10—C11—C16—C269.44 (19)C33—C32—Fe1—C28164.92 (14)
C7—C11—C16—C26123.43 (14)C36—C32—Fe1—C28−76.96 (19)
N3—C11—C16—C1713.11 (15)C36—C32—Fe1—C33118.1 (2)
C10—C11—C16—C17134.70 (14)C33—C32—Fe1—C3179.02 (17)
C7—C11—C16—C17−111.31 (14)C36—C32—Fe1—C31−162.85 (16)
C26—C16—C17—C18134.85 (13)C33—C32—Fe1—C29−160.4 (2)
C11—C16—C17—C1811.52 (15)C36—C32—Fe1—C29−42.3 (3)
C26—C16—C17—C20−100.24 (15)C33—C32—Fe1—C3045.0 (4)
C11—C16—C17—C20136.43 (13)C36—C32—Fe1—C30163.1 (3)
C20—C17—C18—N3−155.76 (13)C33—C34—Fe1—C35119.8 (3)
C16—C17—C18—N3−32.34 (16)C33—C34—Fe1—C27−42.2 (4)
C18—C17—C20—C21−125.50 (18)C35—C34—Fe1—C27−162.0 (3)
C16—C17—C20—C21115.89 (18)C33—C34—Fe1—C3682.0 (2)
C18—C17—C20—C2555.8 (2)C35—C34—Fe1—C36−37.8 (2)
C16—C17—C20—C25−62.8 (2)C33—C34—Fe1—C3237.94 (17)
C25—C20—C21—C221.3 (3)C35—C34—Fe1—C32−81.8 (2)
C17—C20—C21—C22−177.46 (18)C33—C34—Fe1—C28156.3 (2)
C20—C21—C22—C23−1.6 (3)C35—C34—Fe1—C2836.5 (4)
C21—C22—C23—C240.9 (3)C35—C34—Fe1—C33−119.8 (3)
C21—C22—C23—C37−178.43 (19)C33—C34—Fe1—C31−81.20 (18)
C22—C23—C24—C25−0.1 (3)C35—C34—Fe1—C31159.02 (19)
C37—C23—C24—C25179.34 (18)C33—C34—Fe1—C29−166.04 (14)
C23—C24—C25—C20−0.2 (3)C35—C34—Fe1—C2974.2 (2)
C21—C20—C25—C24−0.4 (3)C33—C34—Fe1—C30−123.52 (16)
C17—C20—C25—C24178.36 (16)C35—C34—Fe1—C30116.7 (2)
C17—C16—C26—O1−26.9 (2)C29—C28—Fe1—C3577.86 (18)
C11—C16—C26—O193.32 (17)C27—C28—Fe1—C35−163.05 (16)
C17—C16—C26—C27154.99 (13)C29—C28—Fe1—C27−119.08 (15)
C11—C16—C26—C27−84.80 (15)C29—C28—Fe1—C36118.36 (16)
O1—C26—C27—C281.6 (2)C27—C28—Fe1—C36−122.55 (15)
C16—C26—C27—C28179.68 (14)C29—C28—Fe1—C32159.35 (14)
O1—C26—C27—C31172.55 (16)C27—C28—Fe1—C32−81.57 (15)
C16—C26—C27—C31−9.3 (2)C29—C28—Fe1—C3451.2 (3)
O1—C26—C27—Fe186.68 (17)C27—C28—Fe1—C34170.3 (3)
C16—C26—C27—Fe1−95.21 (14)C29—C28—Fe1—C33−173.2 (2)
C31—C27—C28—C29−0.34 (19)C27—C28—Fe1—C33−54.1 (3)
C26—C27—C28—C29172.13 (15)C29—C28—Fe1—C31−80.23 (12)
Fe1—C27—C28—C2959.96 (13)C27—C28—Fe1—C3138.85 (10)
C31—C27—C28—Fe1−60.29 (11)C27—C28—Fe1—C29119.08 (15)
C26—C27—C28—Fe1112.17 (15)C29—C28—Fe1—C30−37.05 (11)
C27—C28—C29—C300.0 (2)C27—C28—Fe1—C3082.03 (11)
Fe1—C28—C29—C3058.96 (14)C34—C33—Fe1—C35−37.09 (19)
C27—C28—C29—Fe1−58.93 (12)C32—C33—Fe1—C3581.8 (2)
C28—C29—C30—C310.3 (2)C34—C33—Fe1—C27163.53 (16)
Fe1—C29—C30—C3158.72 (13)C32—C33—Fe1—C27−77.54 (17)
C28—C29—C30—Fe1−58.43 (13)C34—C33—Fe1—C36−80.7 (2)
C29—C30—C31—C27−0.5 (2)C32—C33—Fe1—C3638.20 (18)
Fe1—C30—C31—C2758.50 (11)C34—C33—Fe1—C32−118.9 (2)
C29—C30—C31—Fe1−59.00 (14)C32—C33—Fe1—C34118.9 (2)
C28—C27—C31—C300.51 (19)C34—C33—Fe1—C28−156.4 (2)
C26—C27—C31—C30−171.81 (15)C32—C33—Fe1—C28−37.4 (3)
Fe1—C27—C31—C30−59.76 (12)C34—C33—Fe1—C31118.88 (17)
C28—C27—C31—Fe160.28 (11)C32—C33—Fe1—C31−122.19 (16)
C26—C27—C31—Fe1−112.05 (15)C34—C33—Fe1—C2937.1 (4)
C36—C32—C33—C340.1 (3)C32—C33—Fe1—C29156.0 (3)
Fe1—C32—C33—C3459.93 (17)C34—C33—Fe1—C3076.43 (19)
C36—C32—C33—Fe1−59.82 (16)C32—C33—Fe1—C30−164.64 (15)
C32—C33—C34—C35−0.4 (3)C30—C31—Fe1—C35−43.2 (3)
Fe1—C33—C34—C3559.12 (18)C27—C31—Fe1—C35−162.6 (2)
C32—C33—C34—Fe1−59.57 (15)C30—C31—Fe1—C27119.34 (15)
C33—C34—C35—C360.6 (3)C30—C31—Fe1—C36157.9 (3)
Fe1—C34—C35—C3660.33 (18)C27—C31—Fe1—C3638.5 (3)
C33—C34—C35—Fe1−59.72 (18)C30—C31—Fe1—C32−164.77 (13)
C34—C35—C36—C32−0.5 (3)C27—C31—Fe1—C3275.89 (13)
Fe1—C35—C36—C3260.25 (17)C30—C31—Fe1—C34−80.07 (15)
C34—C35—C36—Fe1−60.78 (19)C27—C31—Fe1—C34160.58 (13)
C33—C32—C36—C350.3 (3)C30—C31—Fe1—C2880.78 (12)
Fe1—C32—C36—C35−60.01 (18)C27—C31—Fe1—C28−38.56 (9)
C33—C32—C36—Fe160.27 (15)C30—C31—Fe1—C33−122.11 (13)
C8—C7—N1—C6−2.9 (2)C27—C31—Fe1—C33118.55 (12)
C11—C7—N1—C6178.34 (14)C30—C31—Fe1—C2937.17 (11)
C1—C6—N1—C7−177.38 (15)C27—C31—Fe1—C29−82.17 (11)
C5—C6—N1—C72.0 (2)C27—C31—Fe1—C30−119.34 (15)
C7—C8—N2—C51.4 (2)C30—C29—Fe1—C35119.88 (16)
C9—C8—N2—C5−175.84 (16)C28—C29—Fe1—C35−120.06 (16)
C6—C5—N2—C8−2.2 (2)C30—C29—Fe1—C27−81.86 (12)
C4—C5—N2—C8175.73 (17)C28—C29—Fe1—C2738.20 (10)
C17—C18—N3—C19175.16 (14)C30—C29—Fe1—C36161.28 (16)
C17—C18—N3—C1143.41 (16)C28—C29—Fe1—C36−78.66 (17)
C10—C11—N3—C1968.04 (18)C30—C29—Fe1—C32−168.4 (2)
C7—C11—N3—C19−46.10 (19)C28—C29—Fe1—C32−48.4 (3)
C16—C11—N3—C19−165.80 (14)C30—C29—Fe1—C3479.95 (16)
C10—C11—N3—C18−161.05 (13)C28—C29—Fe1—C34−159.99 (14)
C7—C11—N3—C1884.81 (16)C30—C29—Fe1—C28−120.06 (16)
C16—C11—N3—C18−34.89 (15)C30—C29—Fe1—C3352.4 (3)
C34—C35—Fe1—C27162.4 (2)C28—C29—Fe1—C33172.5 (2)
C36—C35—Fe1—C2743.7 (4)C30—C29—Fe1—C31−36.99 (11)
C34—C35—Fe1—C36118.7 (3)C28—C29—Fe1—C3183.07 (11)
C34—C35—Fe1—C3280.7 (2)C28—C29—Fe1—C30120.06 (16)
C36—C35—Fe1—C32−38.04 (17)C31—C30—Fe1—C35162.08 (14)
C36—C35—Fe1—C34−118.7 (3)C29—C30—Fe1—C35−77.92 (17)
C34—C35—Fe1—C28−165.24 (16)C31—C30—Fe1—C27−38.35 (10)
C36—C35—Fe1—C2876.0 (2)C29—C30—Fe1—C2781.65 (12)
C34—C35—Fe1—C3336.79 (18)C31—C30—Fe1—C36−163.0 (2)
C36—C35—Fe1—C33−81.92 (19)C29—C30—Fe1—C36−43.0 (3)
C34—C35—Fe1—C31−51.2 (4)C31—C30—Fe1—C3244.5 (3)
C36—C35—Fe1—C31−169.9 (2)C29—C30—Fe1—C32164.5 (3)
C34—C35—Fe1—C29−123.77 (19)C31—C30—Fe1—C34119.85 (14)
C36—C35—Fe1—C29117.52 (18)C29—C30—Fe1—C34−120.15 (14)
C34—C35—Fe1—C30−82.4 (2)C31—C30—Fe1—C28−82.81 (11)
C36—C35—Fe1—C30158.85 (17)C29—C30—Fe1—C2837.19 (11)
C28—C27—Fe1—C3543.5 (3)C31—C30—Fe1—C3378.96 (15)
C31—C27—Fe1—C35161.4 (3)C29—C30—Fe1—C33−161.03 (13)
C26—C27—Fe1—C35−76.7 (3)C29—C30—Fe1—C31120.00 (16)
C28—C27—Fe1—C3675.58 (16)C31—C30—Fe1—C29−120.00 (16)
C31—C27—Fe1—C36−166.46 (14)
D—H···AD—HH···AD···AD—H···A
C28—H28···N3i0.932.493.416 (2)176
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
C28—H28⋯N3i 0.932.493.416 (2)176

Symmetry code: (i) .

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

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Authors:  Gérard Jaouen; Siden Top; Anne Vessières; G Leclercq; Michael J McGlinchey
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Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-11-10

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Authors:  E Theboral Sugi Kamala; S Nirmala; L Sudha; S Kathiravan; R Raghunathan
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-05-29

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