metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 12| December 2012| Pages m1576-m1577

4-Ferrocenyl-1-methyl-3-benzoyl­spiro­[pyrrolidine-2,11′-indeno­[1,2-b]quinoxaline]

aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Maraimalai (Guindy) Campus, Chennai 600 025, India, and bDepartment of Organic Chemistry, University of Madras, Maraimalai (Guindy) Campus, Chennai 600 025, India
*Correspondence e-mail: shirai2011@gmail.com

(Received 17 November 2012; accepted 25 November 2012; online 30 November 2012)

In the title compound, [Fe(C5H5)(C31H24N3O)], the pyrrolidine ring adopts a twist conformation. The pyrrolidine ring is almost perpendicular to the indeno­quinoxaline ring system, making a dihedral angle of 84.44 (5)°. The cyclo­penta­dienyl rings of the ferrocene moiety adopt an eclipsed conformation. The crystal packing features weak C—H⋯N and C—H⋯π inter­actions.

Related literature

For the biological activity of ferrocene derivatives, see: Jaouen et al. (2004[Jaouen, G., Top, S., Vessireres, A., Leclercq, G., Vaissermann, J. & McGlinchey, M. J. (2004). Curr. Med. Chem. 11, 2505-2517.]); Biot et al. (2004[Biot, C., Dessolin, J., Richard, I. & Dive, D. (2004). J. Organomet. Chem. 689, 4678-4682.]); Fouda et al. (2007[Fouda, M. F. R., Abd-Elzaher, M. M., Abdelsamaia, R. A. & Labib, A. A. (2007). Appl. Organomet. Chem. 21, 613-625.]). For related structures, see: Kamala et al. (2009[Kamala, E. T. S., Nirmala, S., Sudha, L., Kathiravan, S. & Raghunathan, R. (2009). Acta Cryst. E65, m687-m688.]); Gunasekaran et al. (2010[Gunasekaran, B., Kathiravan, S., Raghunathan, R. & Manivannan, V. (2010). Acta Cryst. E66, m1543.]); Vijayakumar et al. (2012[Vijayakumar, B., Gavaskar, D., Srinivasan, T., Raghunathan, R. & Velmurugan, D. (2012). Acta Cryst. E68, m1382-m1383.]); For puckering and asymmetry parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]); Nardelli (1983[Nardelli, M. (1983). Acta Cryst. C39, 1141-1142.]).

[Scheme 1]

Experimental

Crystal data
  • [Fe(C5H5)(C31H24N3O)]

  • Mr = 575.47

  • Monoclinic, P 21 /c

  • a = 10.8091 (18) Å

  • b = 12.326 (2) Å

  • c = 20.989 (3) Å

  • β = 100.654 (8)°

  • V = 2748.2 (8) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.58 mm−1

  • T = 293 K

  • 0.2 × 0.2 × 0.2 mm

Data collection
  • Bruker SMART APEXII area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.890, Tmax = 0.890

  • 27206 measured reflections

  • 6927 independent reflections

  • 5624 reflections with I > 2σ(I)

  • Rint = 0.028

Refinement
  • R[F2 > 2σ(F2)] = 0.036

  • wR(F2) = 0.106

  • S = 1.01

  • 6927 reflections

  • 371 parameters

  • H-atom parameters constrained

  • Δρmax = 0.30 e Å−3

  • Δρmin = −0.44 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C20–C24 ring.

D—H⋯A D—H H⋯A DA D—H⋯A
C25—H25⋯N3 0.93 2.55 3.351 (2) 144
C35—H35⋯Cg3i 0.93 2.83 3.616 (2) 143
Symmetry code: (i) [-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Ferrocene attached compounds are well known to have biological activities like antimalarial, antifungal (Biot et al., 2004), antitumor (Jaouen et al., 2004), and antibacterial (Fouda et al., 2007). Against this background, the information of molecular conformations and crystal packing of title compound was obtained and analyzed using X-ray diffraction study. The bond lengths and angles of titled compound agree with those observed in other ferrocene derivative 3'-Ferrocenylcarbonyl-1'-methyl-4'- phenylspiro[indeno[2,3-b]quinoxaline-11,2'-pyrrolidine] (Vijayakumar et al. 2012).

The pyrrolidine ring adopts a twisted conformation with the puckering parameters q2 and ϕ and the smallest displacement asymmetric parameters, δ, as follows: q2 = 0.399 (1) A, ϕ = 26.0 (2)° and Δ2(C17) =7.29 (14)°. The dihedral angle between the pyrrolidine ring and indeno-quinoxaline ring system is 84.44 (5)° which clearly shows that the both rings are almost perpendicular to each other. The Cg3 (C20—C24) and Cg4 (C25—C29) are the centroids cyclopentadinene rings where the Fe1-Cg3 and Fe1-Cg4 distances are 1.6466 (8) and 1.6512 (10) Å, respectively and the Cg3-Fe1-Cg4 angle is 179.40 (5)°. In addition to the van der Waals interactions, the crystal packing (Fig.2) is stabilized by weak C—H···N and C—H···π interactions (Table 1).

Related literature top

For the biological activity of ferrocene derivatives, see: Jaouen et al. (2004); Biot et al. (2004); Fouda et al. (2007). For related structures, see: Kamala et al. (2009); Gunasekaran et al. (2010); Vijayakumar et al. (2012); For puckering and asymmetry parameters, see: Cremer & Pople (1975); Nardelli (1983).

Experimental top

Ninhydrin (1 mM) and 1, 2-phenylenediamine (1 mM) were mixed and stirred with 10mL of methanol for 10 min. To this mixture 1 mM of Sarcosine and 1 mM of ferrocene derived dipolarophile were added and was refluxed up to the end of the reaction as observed by TLC. The solvent content from the mixture was removed under reduced pressure and the crude product was obtained. Using column chromatography the crude extract was purified by 4:1 ratio of petroleum ether and ethyl acetate. Finally, single crystals suitable for the X-ray diffraction were obtained by slow evaporation at room temperature.

Refinement top

Hydrogen atoms were placed in calculated positions with C—H ranging from 0.93Å to 0.98Å and refined using the riding model approximation with a fixed isotropic displacement parameter of Uiso(H) = 1.2 Ueq(C).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound, showing displacement ellipsoids drawn at the 30% probability level. H atoms are presented as a small spheres of arbitrary radius.
[Figure 2] Fig. 2. The molecular packing viewed down the a axis.
4-Ferrocenyl-1-methyl-3-benzoylspiro[pyrrolidine-2,11'- indeno[1,2-b]quinoxaline] top
Crystal data top
[Fe(C5H5)(C31H24N3O)]Z = 4
Mr = 575.47F(000) = 1200
Monoclinic, P21/cDx = 1.391 Mg m3
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 10.8091 (18) Åθ = 2.0–28.3°
b = 12.326 (2) ŵ = 0.58 mm1
c = 20.989 (3) ÅT = 293 K
β = 100.654 (8)°Block, brown
V = 2748.2 (8) Å30.2 × 0.2 × 0.2 mm
Data collection top
Bruker SMART APEXII area-detector
diffractometer
6927 independent reflections
Radiation source: fine-focus sealed tube5624 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
ω and ϕ scansθmax = 28.6°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
h = 1414
Tmin = 0.890, Tmax = 0.890k = 1614
27206 measured reflectionsl = 2827
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)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0582P)2 + 0.6864P]
where P = (Fo2 + 2Fc2)/3
6927 reflections(Δ/σ)max = 0.002
371 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = 0.44 e Å3
Crystal data top
[Fe(C5H5)(C31H24N3O)]V = 2748.2 (8) Å3
Mr = 575.47Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.8091 (18) ŵ = 0.58 mm1
b = 12.326 (2) ÅT = 293 K
c = 20.989 (3) Å0.2 × 0.2 × 0.2 mm
β = 100.654 (8)°
Data collection top
Bruker SMART APEXII area-detector
diffractometer
6927 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
5624 reflections with I > 2σ(I)
Tmin = 0.890, Tmax = 0.890Rint = 0.028
27206 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0360 restraints
wR(F2) = 0.106H-atom parameters constrained
S = 1.01Δρmax = 0.30 e Å3
6927 reflectionsΔρmin = 0.44 e Å3
371 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.79681 (14)0.51846 (13)0.70367 (8)0.0417 (3)
H10.83970.50590.74570.050*
C20.80655 (16)0.61717 (14)0.67526 (9)0.0480 (4)
H20.85610.67130.69800.058*
C30.74260 (17)0.63721 (15)0.61233 (9)0.0513 (4)
H30.74940.70480.59360.062*
C40.67032 (16)0.55878 (14)0.57805 (9)0.0475 (4)
H40.62840.57330.53610.057*
C50.65853 (13)0.45581 (12)0.60556 (7)0.0351 (3)
C60.72248 (13)0.43585 (12)0.66985 (7)0.0332 (3)
C70.63802 (12)0.26813 (11)0.66576 (6)0.0314 (3)
C80.57653 (13)0.28695 (12)0.60063 (6)0.0323 (3)
C90.50426 (13)0.19007 (12)0.57774 (7)0.0345 (3)
C100.52049 (13)0.11230 (12)0.62698 (7)0.0339 (3)
C110.60275 (13)0.15690 (11)0.68865 (6)0.0314 (3)
C120.45706 (15)0.01405 (13)0.61673 (8)0.0422 (3)
H120.46720.03880.64890.051*
C130.37828 (15)0.00376 (14)0.55751 (8)0.0459 (4)
H130.33440.06880.55040.055*
C140.36392 (15)0.07330 (15)0.50904 (8)0.0469 (4)
H140.31120.05930.46960.056*
C150.42706 (15)0.17096 (14)0.51848 (7)0.0424 (3)
H150.41790.22280.48570.051*
C160.71773 (12)0.08849 (11)0.72140 (6)0.0306 (3)
H160.77930.13760.74660.037*
C170.66473 (13)0.01436 (12)0.76915 (7)0.0334 (3)
H170.64550.05630.74830.040*
C180.53991 (14)0.06744 (14)0.77724 (8)0.0414 (3)
H18A0.46900.02260.75800.050*
H18B0.53730.07830.82270.050*
C190.41254 (17)0.22002 (16)0.72858 (9)0.0522 (4)
H19A0.35450.16940.70450.078*
H19B0.41590.28440.70320.078*
H19C0.38500.23860.76810.078*
C200.75808 (14)0.00309 (11)0.83087 (7)0.0340 (3)
C210.73116 (17)0.03810 (13)0.89135 (7)0.0433 (4)
H210.65160.05140.90050.052*
C220.84766 (19)0.04913 (14)0.93543 (8)0.0506 (4)
H220.85710.07040.97860.061*
C230.94568 (17)0.02255 (14)0.90278 (8)0.0499 (4)
H231.03120.02330.92040.060*
C240.89125 (15)0.00566 (13)0.83792 (8)0.0404 (3)
H240.93510.02620.80570.048*
C250.7390 (2)0.25002 (16)0.87637 (10)0.0648 (6)
H250.67860.26280.83940.078*
C260.7154 (2)0.21523 (17)0.93713 (11)0.0692 (6)
H260.63710.20040.94740.083*
C270.8317 (3)0.20723 (18)0.97903 (10)0.0738 (7)
H270.84390.18661.02230.089*
C280.9260 (3)0.23524 (18)0.94526 (13)0.0755 (7)
H281.01190.23620.96190.091*
C290.8690 (3)0.26178 (16)0.88154 (12)0.0723 (6)
H290.91050.28340.84860.087*
C300.78362 (13)0.02473 (12)0.67524 (7)0.0352 (3)
C310.89465 (13)0.07269 (13)0.65201 (7)0.0359 (3)
C320.95018 (16)0.01150 (17)0.60885 (9)0.0523 (4)
H320.91620.05540.59460.063*
C331.05538 (18)0.0497 (2)0.58717 (10)0.0638 (5)
H331.09200.00820.55860.077*
C341.10601 (17)0.14888 (19)0.60772 (10)0.0590 (5)
H341.17640.17440.59280.071*
C351.05280 (17)0.21050 (15)0.65028 (10)0.0525 (4)
H351.08750.27740.66420.063*
C360.94712 (15)0.17263 (13)0.67245 (8)0.0423 (3)
H360.91130.21450.70110.051*
N10.71034 (11)0.33856 (10)0.70041 (6)0.0347 (3)
N20.58371 (12)0.37874 (10)0.57026 (6)0.0375 (3)
N30.53706 (11)0.17117 (11)0.74359 (6)0.0367 (3)
O10.74771 (12)0.06575 (10)0.65798 (6)0.0535 (3)
Fe10.82624 (2)0.106179 (18)0.901638 (10)0.04051 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0384 (8)0.0414 (9)0.0436 (8)0.0029 (6)0.0034 (6)0.0010 (7)
C20.0429 (8)0.0394 (9)0.0605 (10)0.0091 (7)0.0063 (7)0.0014 (7)
C30.0542 (10)0.0364 (8)0.0620 (11)0.0066 (7)0.0072 (8)0.0125 (8)
C40.0540 (9)0.0402 (9)0.0468 (9)0.0024 (7)0.0050 (7)0.0129 (7)
C50.0361 (7)0.0335 (7)0.0362 (7)0.0010 (6)0.0080 (5)0.0042 (6)
C60.0311 (6)0.0316 (7)0.0378 (7)0.0020 (5)0.0087 (5)0.0024 (6)
C70.0326 (6)0.0308 (7)0.0308 (6)0.0025 (5)0.0056 (5)0.0039 (5)
C80.0331 (6)0.0331 (7)0.0303 (6)0.0026 (5)0.0051 (5)0.0030 (5)
C90.0340 (7)0.0351 (7)0.0335 (7)0.0011 (6)0.0033 (5)0.0011 (6)
C100.0325 (6)0.0336 (7)0.0346 (7)0.0001 (5)0.0034 (5)0.0013 (5)
C110.0329 (6)0.0303 (7)0.0304 (6)0.0001 (5)0.0041 (5)0.0044 (5)
C120.0428 (8)0.0370 (8)0.0453 (8)0.0047 (6)0.0043 (6)0.0039 (6)
C130.0417 (8)0.0406 (9)0.0533 (9)0.0076 (7)0.0032 (7)0.0079 (7)
C140.0421 (8)0.0514 (10)0.0431 (8)0.0023 (7)0.0025 (6)0.0073 (7)
C150.0453 (8)0.0433 (9)0.0351 (7)0.0004 (7)0.0018 (6)0.0022 (6)
C160.0309 (6)0.0296 (7)0.0305 (6)0.0013 (5)0.0037 (5)0.0047 (5)
C170.0368 (7)0.0309 (7)0.0317 (6)0.0032 (5)0.0041 (5)0.0059 (5)
C180.0364 (7)0.0469 (9)0.0416 (8)0.0014 (6)0.0097 (6)0.0133 (7)
C190.0478 (9)0.0547 (11)0.0567 (10)0.0158 (8)0.0169 (8)0.0109 (8)
C200.0423 (7)0.0258 (7)0.0328 (7)0.0015 (5)0.0042 (5)0.0039 (5)
C210.0561 (9)0.0358 (8)0.0368 (7)0.0023 (7)0.0055 (6)0.0084 (6)
C220.0760 (12)0.0375 (9)0.0335 (7)0.0053 (8)0.0028 (7)0.0063 (6)
C230.0516 (9)0.0430 (9)0.0476 (9)0.0111 (7)0.0103 (7)0.0004 (7)
C240.0416 (8)0.0373 (8)0.0402 (8)0.0070 (6)0.0022 (6)0.0009 (6)
C250.0948 (16)0.0362 (9)0.0540 (11)0.0184 (10)0.0106 (10)0.0076 (8)
C260.0904 (16)0.0484 (11)0.0713 (13)0.0181 (11)0.0213 (12)0.0116 (10)
C270.122 (2)0.0503 (12)0.0429 (10)0.0134 (12)0.0008 (12)0.0095 (9)
C280.0866 (16)0.0472 (12)0.0813 (16)0.0079 (11)0.0144 (13)0.0178 (11)
C290.116 (2)0.0349 (10)0.0681 (13)0.0096 (11)0.0222 (13)0.0052 (9)
C300.0360 (7)0.0339 (7)0.0343 (7)0.0012 (6)0.0026 (5)0.0026 (6)
C310.0330 (7)0.0399 (8)0.0340 (7)0.0051 (6)0.0042 (5)0.0051 (6)
C320.0416 (8)0.0631 (12)0.0527 (9)0.0003 (8)0.0102 (7)0.0130 (8)
C330.0474 (10)0.0894 (16)0.0589 (11)0.0020 (10)0.0213 (8)0.0131 (11)
C340.0423 (9)0.0791 (14)0.0595 (11)0.0001 (9)0.0194 (8)0.0125 (10)
C350.0469 (9)0.0459 (10)0.0655 (11)0.0037 (7)0.0129 (8)0.0134 (8)
C360.0423 (8)0.0374 (8)0.0488 (8)0.0022 (6)0.0127 (6)0.0047 (7)
N10.0363 (6)0.0336 (6)0.0331 (6)0.0005 (5)0.0037 (5)0.0023 (5)
N20.0431 (7)0.0343 (7)0.0337 (6)0.0006 (5)0.0037 (5)0.0055 (5)
N30.0369 (6)0.0386 (7)0.0359 (6)0.0032 (5)0.0101 (5)0.0066 (5)
O10.0592 (7)0.0420 (7)0.0625 (8)0.0106 (6)0.0195 (6)0.0132 (6)
Fe10.05287 (15)0.03087 (13)0.03530 (13)0.00303 (9)0.00166 (9)0.00061 (8)
Geometric parameters (Å, º) top
C1—C21.368 (2)C20—C211.421 (2)
C1—C61.405 (2)C20—C241.424 (2)
C1—H10.9300C20—Fe12.0393 (14)
C2—C31.395 (3)C21—C221.425 (2)
C2—H20.9300C21—Fe12.0454 (17)
C3—C41.362 (3)C21—H210.9300
C3—H30.9300C22—C231.403 (3)
C4—C51.410 (2)C22—Fe12.0398 (17)
C4—H40.9300C22—H220.9300
C5—N21.3727 (19)C23—C241.423 (2)
C5—C61.419 (2)C23—Fe12.0430 (17)
C6—N11.3777 (19)C23—H230.9300
C7—N11.2975 (18)C24—Fe12.0409 (16)
C7—C81.4241 (18)C24—H240.9300
C7—C111.5244 (19)C25—C291.397 (4)
C8—N21.3081 (18)C25—C261.413 (3)
C8—C91.459 (2)C25—Fe12.0320 (19)
C9—C151.3839 (19)C25—H250.9300
C9—C101.397 (2)C26—C271.398 (3)
C10—C121.389 (2)C26—Fe12.031 (2)
C10—C111.5306 (19)C26—H260.9300
C11—N31.4724 (18)C27—C281.388 (4)
C11—C161.5531 (18)C27—Fe12.039 (2)
C12—C131.388 (2)C27—H270.9300
C12—H120.9300C28—C291.404 (3)
C13—C141.379 (3)C28—Fe12.041 (2)
C13—H130.9300C28—H280.9300
C14—C151.380 (2)C29—Fe12.035 (2)
C14—H140.9300C29—H290.9300
C15—H150.9300C30—O11.2141 (19)
C16—C301.523 (2)C30—C311.498 (2)
C16—C171.5428 (19)C31—C361.390 (2)
C16—H160.9800C31—C321.397 (2)
C17—C201.5031 (19)C32—C331.383 (3)
C17—C181.537 (2)C32—H320.9300
C17—H170.9800C33—C341.376 (3)
C18—N31.458 (2)C33—H330.9300
C18—H18A0.9700C34—C351.377 (3)
C18—H18B0.9700C34—H340.9300
C19—N31.455 (2)C35—C361.391 (2)
C19—H19A0.9600C35—H350.9300
C19—H19B0.9600C36—H360.9300
C19—H19C0.9600
C2—C1—C6120.49 (15)C29—C25—C26107.95 (19)
C2—C1—H1119.8C29—C25—Fe170.05 (12)
C6—C1—H1119.8C26—C25—Fe169.63 (11)
C1—C2—C3120.38 (16)C29—C25—H25126.0
C1—C2—H2119.8C26—C25—H25126.0
C3—C2—H2119.8Fe1—C25—H25125.9
C4—C3—C2120.66 (16)C27—C26—C25107.3 (2)
C4—C3—H3119.7C27—C26—Fe170.21 (13)
C2—C3—H3119.7C25—C26—Fe169.68 (12)
C3—C4—C5120.61 (16)C27—C26—H26126.3
C3—C4—H4119.7C25—C26—H26126.3
C5—C4—H4119.7Fe1—C26—H26125.4
N2—C5—C4119.40 (13)C28—C27—C26108.7 (2)
N2—C5—C6121.87 (13)C28—C27—Fe170.20 (12)
C4—C5—C6118.71 (14)C26—C27—Fe169.62 (12)
N1—C6—C1119.36 (13)C28—C27—H27125.6
N1—C6—C5121.47 (13)C26—C27—H27125.6
C1—C6—C5119.14 (14)Fe1—C27—H27126.1
N1—C7—C8123.72 (13)C27—C28—C29108.1 (2)
N1—C7—C11125.80 (12)C27—C28—Fe170.03 (13)
C8—C7—C11110.45 (12)C29—C28—Fe169.63 (12)
N2—C8—C7123.33 (13)C27—C28—H28126.0
N2—C8—C9128.60 (12)C29—C28—H28126.0
C7—C8—C9108.02 (12)Fe1—C28—H28126.0
C15—C9—C10121.37 (14)C25—C29—C28107.9 (2)
C15—C9—C8129.24 (14)C25—C29—Fe169.78 (12)
C10—C9—C8109.37 (12)C28—C29—Fe170.08 (13)
C12—C10—C9119.54 (13)C25—C29—H29126.0
C12—C10—C11129.59 (13)C28—C29—H29126.0
C9—C10—C11110.67 (12)Fe1—C29—H29125.7
N3—C11—C7108.92 (12)O1—C30—C31119.77 (14)
N3—C11—C10114.60 (12)O1—C30—C16120.18 (14)
C7—C11—C10101.34 (11)C31—C30—C16120.04 (13)
N3—C11—C16100.40 (10)C36—C31—C32118.61 (15)
C7—C11—C16113.68 (11)C36—C31—C30123.70 (14)
C10—C11—C16118.13 (12)C32—C31—C30117.66 (15)
C10—C12—C13118.70 (15)C33—C32—C31120.51 (18)
C10—C12—H12120.6C33—C32—H32119.7
C13—C12—H12120.6C31—C32—H32119.7
C14—C13—C12121.21 (15)C34—C33—C32120.18 (18)
C14—C13—H13119.4C34—C33—H33119.9
C12—C13—H13119.4C32—C33—H33119.9
C15—C14—C13120.64 (15)C33—C34—C35120.27 (17)
C15—C14—H14119.7C33—C34—H34119.9
C13—C14—H14119.7C35—C34—H34119.9
C14—C15—C9118.53 (15)C34—C35—C36119.95 (18)
C14—C15—H15120.7C34—C35—H35120.0
C9—C15—H15120.7C36—C35—H35120.0
C30—C16—C17112.41 (12)C31—C36—C35120.48 (16)
C30—C16—C11115.39 (11)C31—C36—H36119.8
C17—C16—C11104.26 (11)C35—C36—H36119.8
C30—C16—H16108.2C7—N1—C6114.88 (12)
C17—C16—H16108.2C8—N2—C5114.69 (12)
C11—C16—H16108.2C19—N3—C18113.81 (13)
C20—C17—C18115.40 (12)C19—N3—C11116.15 (12)
C20—C17—C16111.96 (11)C18—N3—C11107.73 (12)
C18—C17—C16104.99 (11)C25—Fe1—C2640.69 (9)
C20—C17—H17108.1C25—Fe1—C2940.17 (10)
C18—C17—H17108.1C26—Fe1—C2967.93 (11)
C16—C17—H17108.1C25—Fe1—C20107.37 (7)
N3—C18—C17105.08 (11)C26—Fe1—C20123.10 (9)
N3—C18—H18A110.7C29—Fe1—C20122.47 (8)
C17—C18—H18A110.7C25—Fe1—C22157.98 (10)
N3—C18—H18B110.7C26—Fe1—C22122.02 (9)
C17—C18—H18B110.7C29—Fe1—C22160.21 (10)
H18A—C18—H18B108.8C20—Fe1—C2268.65 (6)
N3—C19—H19A109.5C25—Fe1—C2767.58 (8)
N3—C19—H19B109.5C26—Fe1—C2740.17 (10)
H19A—C19—H19B109.5C29—Fe1—C2767.37 (10)
N3—C19—H19C109.5C20—Fe1—C27159.57 (10)
H19A—C19—H19C109.5C22—Fe1—C27108.15 (8)
H19B—C19—H19C109.5C25—Fe1—C2867.55 (10)
C21—C20—C24107.48 (13)C26—Fe1—C2867.55 (11)
C21—C20—C17126.70 (14)C29—Fe1—C2840.28 (10)
C24—C20—C17125.70 (13)C20—Fe1—C28158.62 (10)
C21—C20—Fe169.88 (9)C22—Fe1—C28123.98 (8)
C24—C20—Fe169.64 (8)C27—Fe1—C2839.77 (11)
C17—C20—Fe1128.88 (10)C25—Fe1—C23160.48 (9)
C20—C21—C22107.87 (15)C26—Fe1—C23157.49 (9)
C20—C21—Fe169.41 (9)C29—Fe1—C23124.55 (10)
C22—C21—Fe169.38 (10)C20—Fe1—C2368.77 (6)
C20—C21—H21126.1C22—Fe1—C2340.19 (8)
C22—C21—H21126.1C27—Fe1—C23122.67 (8)
Fe1—C21—H21126.7C28—Fe1—C23108.65 (9)
C23—C22—C21108.49 (14)C25—Fe1—C24123.92 (8)
C23—C22—Fe170.03 (10)C26—Fe1—C24160.03 (8)
C21—C22—Fe169.80 (9)C29—Fe1—C24108.51 (9)
C23—C22—H22125.8C20—Fe1—C2440.84 (6)
C21—C22—H22125.8C22—Fe1—C2468.12 (7)
Fe1—C22—H22126.0C27—Fe1—C24158.44 (9)
C22—C23—C24107.97 (15)C28—Fe1—C24123.35 (10)
C22—C23—Fe169.78 (10)C23—Fe1—C2440.78 (6)
C24—C23—Fe169.53 (9)C25—Fe1—C21122.09 (9)
C22—C23—H23126.0C26—Fe1—C21107.18 (9)
C24—C23—H23126.0C29—Fe1—C21157.89 (9)
Fe1—C23—H23126.2C20—Fe1—C2140.71 (6)
C20—C24—C23108.19 (15)C22—Fe1—C2140.82 (7)
C20—C24—Fe169.52 (9)C27—Fe1—C21123.73 (10)
C23—C24—Fe169.69 (10)C28—Fe1—C21159.79 (9)
C20—C24—H24125.9C23—Fe1—C2168.28 (8)
C23—C24—H24125.9C24—Fe1—C2168.29 (7)
Fe1—C24—H24126.5
C6—C1—C2—C30.1 (3)C25—C26—Fe1—C22161.76 (12)
C1—C2—C3—C40.5 (3)C25—C26—Fe1—C27118.1 (2)
C2—C3—C4—C50.1 (3)C27—C26—Fe1—C2836.90 (15)
C3—C4—C5—N2179.13 (16)C25—C26—Fe1—C2881.19 (15)
C3—C4—C5—C60.6 (3)C27—C26—Fe1—C2347.7 (3)
C2—C1—C6—N1177.54 (15)C25—C26—Fe1—C23165.8 (2)
C2—C1—C6—C50.6 (2)C27—C26—Fe1—C24164.1 (2)
N2—C5—C6—N11.4 (2)C25—C26—Fe1—C2446.0 (3)
C4—C5—C6—N1177.16 (14)C27—C26—Fe1—C21122.34 (15)
N2—C5—C6—C1179.44 (14)C25—C26—Fe1—C21119.57 (13)
C4—C5—C6—C10.9 (2)C28—C29—Fe1—C25118.8 (2)
N1—C7—C8—N22.5 (2)C25—C29—Fe1—C2637.98 (13)
C11—C7—C8—N2175.52 (13)C28—C29—Fe1—C2680.85 (17)
N1—C7—C8—C9179.88 (13)C25—C29—Fe1—C2078.16 (14)
C11—C7—C8—C92.13 (16)C28—C29—Fe1—C20163.01 (15)
N2—C8—C9—C150.7 (3)C25—C29—Fe1—C22162.3 (2)
C7—C8—C9—C15178.24 (15)C28—C29—Fe1—C2243.4 (3)
N2—C8—C9—C10177.84 (15)C25—C29—Fe1—C2781.57 (15)
C7—C8—C9—C100.34 (16)C28—C29—Fe1—C2737.26 (16)
C15—C9—C10—C120.7 (2)C25—C29—Fe1—C28118.8 (2)
C8—C9—C10—C12178.05 (14)C25—C29—Fe1—C23163.40 (11)
C15—C9—C10—C11176.03 (14)C28—C29—Fe1—C2377.77 (18)
C8—C9—C10—C112.67 (17)C25—C29—Fe1—C24121.06 (12)
N1—C7—C11—N360.24 (18)C28—C29—Fe1—C24120.12 (16)
C8—C7—C11—N3117.69 (12)C25—C29—Fe1—C2143.3 (3)
N1—C7—C11—C10178.59 (14)C28—C29—Fe1—C21162.2 (2)
C8—C7—C11—C103.48 (15)C21—C20—Fe1—C25119.34 (12)
N1—C7—C11—C1650.78 (19)C24—C20—Fe1—C25122.16 (11)
C8—C7—C11—C16131.29 (12)C17—C20—Fe1—C252.14 (16)
C12—C10—C11—N361.4 (2)C21—C20—Fe1—C2677.46 (13)
C9—C10—C11—N3113.40 (14)C24—C20—Fe1—C26164.04 (11)
C12—C10—C11—C7178.49 (15)C17—C20—Fe1—C2644.02 (17)
C9—C10—C11—C73.70 (15)C21—C20—Fe1—C29160.75 (12)
C12—C10—C11—C1656.6 (2)C24—C20—Fe1—C2980.75 (13)
C9—C10—C11—C16128.57 (13)C17—C20—Fe1—C2939.27 (18)
C9—C10—C12—C130.4 (2)C21—C20—Fe1—C2237.68 (10)
C11—C10—C12—C13174.02 (15)C24—C20—Fe1—C2280.82 (10)
C10—C12—C13—C141.0 (3)C17—C20—Fe1—C22159.16 (16)
C12—C13—C14—C150.6 (3)C21—C20—Fe1—C2747.1 (2)
C13—C14—C15—C90.5 (3)C24—C20—Fe1—C27165.6 (2)
C10—C9—C15—C141.1 (2)C17—C20—Fe1—C2774.4 (3)
C8—C9—C15—C14177.37 (15)C21—C20—Fe1—C28168.0 (2)
N3—C11—C16—C30159.56 (12)C24—C20—Fe1—C2849.5 (2)
C7—C11—C16—C3084.31 (15)C17—C20—Fe1—C2870.5 (3)
C10—C11—C16—C3034.24 (17)C21—C20—Fe1—C2380.96 (11)
N3—C11—C16—C1735.78 (13)C24—C20—Fe1—C2337.54 (10)
C7—C11—C16—C17151.92 (11)C17—C20—Fe1—C23157.56 (16)
C10—C11—C16—C1789.54 (14)C21—C20—Fe1—C24118.50 (13)
C30—C16—C17—C2090.90 (14)C17—C20—Fe1—C24120.02 (17)
C11—C16—C17—C20143.42 (12)C24—C20—Fe1—C21118.50 (13)
C30—C16—C17—C18143.18 (12)C17—C20—Fe1—C21121.48 (18)
C11—C16—C17—C1817.50 (14)C23—C22—Fe1—C25165.56 (18)
C20—C17—C18—N3115.98 (13)C21—C22—Fe1—C2546.0 (2)
C16—C17—C18—N37.78 (15)C23—C22—Fe1—C26161.47 (12)
C18—C17—C20—C2140.0 (2)C21—C22—Fe1—C2678.98 (13)
C16—C17—C20—C21160.02 (14)C23—C22—Fe1—C2946.0 (3)
C18—C17—C20—C24144.52 (15)C21—C22—Fe1—C29165.6 (2)
C16—C17—C20—C2424.5 (2)C23—C22—Fe1—C2081.97 (10)
C18—C17—C20—Fe152.85 (18)C21—C22—Fe1—C2037.58 (10)
C16—C17—C20—Fe167.16 (17)C23—C22—Fe1—C27119.49 (13)
C24—C20—C21—C220.84 (18)C21—C22—Fe1—C27120.96 (13)
C17—C20—C21—C22176.98 (14)C23—C22—Fe1—C2878.46 (15)
Fe1—C20—C21—C2258.91 (12)C21—C22—Fe1—C28161.99 (13)
C24—C20—C21—Fe159.75 (10)C21—C22—Fe1—C23119.55 (14)
C17—C20—C21—Fe1124.11 (15)C23—C22—Fe1—C2437.89 (9)
C20—C21—C22—C230.6 (2)C21—C22—Fe1—C2481.66 (11)
Fe1—C21—C22—C2359.55 (13)C23—C22—Fe1—C21119.55 (14)
C20—C21—C22—Fe158.93 (11)C28—C27—Fe1—C2581.37 (16)
C21—C22—C23—C240.2 (2)C26—C27—Fe1—C2538.47 (15)
Fe1—C22—C23—C2459.26 (12)C28—C27—Fe1—C26119.8 (2)
C21—C22—C23—Fe159.41 (12)C28—C27—Fe1—C2937.72 (15)
C21—C20—C24—C230.75 (18)C26—C27—Fe1—C2982.12 (16)
C17—C20—C24—C23176.94 (14)C28—C27—Fe1—C20160.86 (19)
Fe1—C20—C24—C2359.15 (11)C26—C27—Fe1—C2041.0 (3)
C21—C20—C24—Fe159.90 (11)C28—C27—Fe1—C22121.69 (14)
C17—C20—C24—Fe1123.91 (14)C26—C27—Fe1—C22118.47 (15)
C22—C23—C24—C200.37 (19)C26—C27—Fe1—C28119.8 (2)
Fe1—C23—C24—C2059.04 (11)C28—C27—Fe1—C2379.83 (16)
C22—C23—C24—Fe159.41 (12)C26—C27—Fe1—C23160.33 (14)
C29—C25—C26—C270.6 (2)C28—C27—Fe1—C2445.4 (3)
Fe1—C25—C26—C2760.41 (14)C26—C27—Fe1—C24165.26 (19)
C29—C25—C26—Fe159.81 (14)C28—C27—Fe1—C21164.07 (13)
C25—C26—C27—C280.6 (2)C26—C27—Fe1—C2176.09 (16)
Fe1—C26—C27—C2859.50 (16)C27—C28—Fe1—C2581.45 (15)
C25—C26—C27—Fe160.07 (14)C29—C28—Fe1—C2537.69 (15)
C26—C27—C28—C290.3 (2)C27—C28—Fe1—C2637.26 (14)
Fe1—C27—C28—C2959.46 (15)C29—C28—Fe1—C2681.88 (17)
C26—C27—C28—Fe159.15 (15)C27—C28—Fe1—C29119.1 (2)
C26—C25—C29—C280.4 (2)C27—C28—Fe1—C20161.70 (18)
Fe1—C25—C29—C2859.96 (15)C29—C28—Fe1—C2042.6 (3)
C26—C25—C29—Fe159.55 (14)C27—C28—Fe1—C2277.16 (16)
C27—C28—C29—C250.1 (2)C29—C28—Fe1—C22163.70 (15)
Fe1—C28—C29—C2559.77 (15)C29—C28—Fe1—C27119.1 (2)
C27—C28—C29—Fe159.71 (16)C27—C28—Fe1—C23119.02 (14)
C17—C16—C30—O131.91 (18)C29—C28—Fe1—C23121.84 (16)
C11—C16—C30—O187.47 (17)C27—C28—Fe1—C24161.74 (12)
C17—C16—C30—C31146.91 (12)C29—C28—Fe1—C2479.11 (17)
C11—C16—C30—C3193.71 (15)C27—C28—Fe1—C2141.4 (3)
O1—C30—C31—C36175.78 (15)C29—C28—Fe1—C21160.5 (2)
C16—C30—C31—C363.0 (2)C22—C23—Fe1—C25163.8 (2)
O1—C30—C31—C322.3 (2)C24—C23—Fe1—C2544.5 (3)
C16—C30—C31—C32178.92 (13)C22—C23—Fe1—C2644.8 (3)
C36—C31—C32—C330.2 (3)C24—C23—Fe1—C26164.0 (2)
C30—C31—C32—C33177.96 (17)C22—C23—Fe1—C29162.79 (11)
C31—C32—C33—C340.3 (3)C24—C23—Fe1—C2977.98 (13)
C32—C33—C34—C350.4 (3)C22—C23—Fe1—C2081.63 (10)
C33—C34—C35—C360.3 (3)C24—C23—Fe1—C2037.60 (10)
C32—C31—C36—C350.1 (2)C24—C23—Fe1—C22119.23 (15)
C30—C31—C36—C35177.97 (14)C22—C23—Fe1—C2779.31 (14)
C34—C35—C36—C310.1 (3)C24—C23—Fe1—C27161.46 (13)
C8—C7—N1—C61.1 (2)C22—C23—Fe1—C28120.96 (13)
C11—C7—N1—C6176.57 (13)C24—C23—Fe1—C28119.81 (13)
C1—C6—N1—C7178.75 (13)C22—C23—Fe1—C24119.23 (15)
C5—C6—N1—C70.7 (2)C22—C23—Fe1—C2137.74 (10)
C7—C8—N2—C51.7 (2)C24—C23—Fe1—C2181.49 (11)
C9—C8—N2—C5178.80 (14)C20—C24—Fe1—C2576.82 (13)
C4—C5—N2—C8178.38 (15)C23—C24—Fe1—C25163.60 (13)
C6—C5—N2—C80.1 (2)C20—C24—Fe1—C2642.4 (3)
C17—C18—N3—C19162.64 (13)C23—C24—Fe1—C26162.0 (2)
C17—C18—N3—C1132.35 (15)C20—C24—Fe1—C29118.58 (11)
C7—C11—N3—C1968.72 (17)C23—C24—Fe1—C29121.84 (13)
C10—C11—N3—C1943.96 (18)C23—C24—Fe1—C20119.58 (14)
C16—C11—N3—C19171.64 (14)C20—C24—Fe1—C2282.22 (10)
C7—C11—N3—C18162.30 (11)C23—C24—Fe1—C2237.36 (11)
C10—C11—N3—C1885.02 (14)C20—C24—Fe1—C27166.3 (2)
C16—C11—N3—C1842.66 (14)C23—C24—Fe1—C2746.7 (3)
C29—C25—Fe1—C26118.98 (19)C20—C24—Fe1—C28160.61 (11)
C26—C25—Fe1—C29118.98 (19)C23—C24—Fe1—C2879.81 (14)
C29—C25—Fe1—C20120.09 (13)C20—C24—Fe1—C23119.58 (14)
C26—C25—Fe1—C20120.93 (14)C20—C24—Fe1—C2138.10 (8)
C29—C25—Fe1—C22164.03 (18)C23—C24—Fe1—C2181.48 (11)
C26—C25—Fe1—C2245.1 (3)C20—C21—Fe1—C2579.13 (12)
C29—C25—Fe1—C2780.98 (15)C22—C21—Fe1—C25161.43 (12)
C26—C25—Fe1—C2737.99 (15)C20—C21—Fe1—C26121.14 (11)
C29—C25—Fe1—C2837.80 (14)C22—C21—Fe1—C26119.42 (12)
C26—C25—Fe1—C2881.18 (16)C20—C21—Fe1—C2947.6 (3)
C29—C25—Fe1—C2344.7 (3)C22—C21—Fe1—C29167.1 (2)
C26—C25—Fe1—C23163.7 (2)C22—C21—Fe1—C20119.44 (15)
C29—C25—Fe1—C2478.24 (14)C20—C21—Fe1—C22119.44 (15)
C26—C25—Fe1—C24162.78 (13)C20—C21—Fe1—C27162.09 (11)
C29—C25—Fe1—C21162.25 (12)C22—C21—Fe1—C2778.47 (14)
C26—C25—Fe1—C2178.77 (15)C20—C21—Fe1—C28167.4 (2)
C27—C26—Fe1—C25118.1 (2)C22—C21—Fe1—C2847.9 (3)
C27—C26—Fe1—C2980.59 (16)C20—C21—Fe1—C2382.26 (10)
C25—C26—Fe1—C2937.51 (13)C22—C21—Fe1—C2337.18 (11)
C27—C26—Fe1—C20164.13 (13)C20—C21—Fe1—C2438.22 (9)
C25—C26—Fe1—C2077.78 (15)C22—C21—Fe1—C2481.23 (11)
C27—C26—Fe1—C2280.15 (17)
Hydrogen-bond geometry (Å, º) top
Cg3 is the centroid of the C20–C24 ring.
D—H···AD—HH···AD···AD—H···A
C25—H25···N30.932.553.351 (2)144
C35—H35···Cg3i0.932.833.616 (2)143
Symmetry code: (i) x+2, y+1/2, z+3/2.

Experimental details

Crystal data
Chemical formula[Fe(C5H5)(C31H24N3O)]
Mr575.47
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)10.8091 (18), 12.326 (2), 20.989 (3)
β (°) 100.654 (8)
V3)2748.2 (8)
Z4
Radiation typeMo Kα
µ (mm1)0.58
Crystal size (mm)0.2 × 0.2 × 0.2
Data collection
DiffractometerBruker SMART APEXII area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2008)
Tmin, Tmax0.890, 0.890
No. of measured, independent and
observed [I > 2σ(I)] reflections
27206, 6927, 5624
Rint0.028
(sin θ/λ)max1)0.673
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.106, 1.01
No. of reflections6927
No. of parameters371
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.30, 0.44

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
Cg3 is the centroid of the C20–C24 ring.
D—H···AD—HH···AD···AD—H···A
C25—H25···N30.932.553.351 (2)144
C35—H35···Cg3i0.932.833.616 (2)143
Symmetry code: (i) x+2, y+1/2, z+3/2.
 

Acknowledgements

The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection. BV also thanks the University Grants Commission (UGC), Government of India, New Delhi, for a Meritorious Fellowship.

References

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Volume 68| Part 12| December 2012| Pages m1576-m1577
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