supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportsimilar papers Open access

is2493 scheme

Acta Cryst. (2009). E65, m1673    [ doi:10.1107/S1600536809049629 ]

4'-Ferrocenyl-1'-methylacenapthylene-1-spiro-2'-pyrrolidine-3'-spiro-2''-indane-2,1'',3''(1H)-trione

B. Gunasekaran, S. Kathiravan, R. Raghunathan and V. Manivannan

Abstract top

In the title compound, [Fe(C5H5)(C29H20NO3)], the acenaphthylene ring system makes a dihedral angle of 83.77 (3)° with the indane-1,3-dione ring system. The central pyrrolidine ring exhibits a twist conformation. In the crystal, molecules are linked by a weak intermolecular C-H...O interaction into a chain along the b axis. Two weak intramolecular C-H...O interactions are also present.

Comment top

Metallocenes are known to exhibit a wide range of biological activity. Among them ferrocenyl compounds display interesting antibacterial (Fouda et al., 2007), antitumor (Jaouen et al., 2004), antimalarial and antifungal (Biot et al., 2004) activities. In addition, transition metal complexes derived from ferrocene have attracted great interest due to their applications as precursors for the synthesis of organic as well as organometallic compounds (Johnson & Sames, 2000).

The geometric parameters of the title compound (Fig. 1) agree well with reported similar structures (Stalin Elanchezhian et al., 2008; Kamala et al., 2009). The mean plane of acenaphthylene ring [C1/C5—C14] makes the dihedral angle of 83.77 (3)° with the indanedione ring [C2/C16—C23]. The sum of bond angles around N1 [339.72 (15)°] indicates sp3 hybridization. The Fe1—Cg4 and Fe1—Cg5 distances are 1.6488 (3) and 1.6573 (3) Å, respectively, and the Cg4—Fe1—Cg5 angle is 177.70 (4)°, where Cg4 and Cg5 are the centroids of the substituted and unsubstituted cyclopentadienyl (Cp) rings, respectively. The small dihedral angle of 0.63 (11)° between the unsubstituted and substituted Cp rings exposes that the two Cp rings are essentially parallel to each other.

The molecular structure is stabilized by weak intramolecular C—H···O interactions and the crystal packing is stabilized by a weak intermolecular C—H···O interaction. The interactions C3—H3···O3 generates an S(6) graph set motif and C13—H13···O2 generates an S(7) graph set motif (Bernstein et al., 1995).

Related literature top

For the biological activity of ferrocene derivatives, see: Biot et al. (2004); Fouda et al. (2007); Jaouen et al. (2004); Johnson & Sames (2000). For related structures, see: Stalin Elanchezhian et al. (2008); Kamala et al. (2009). For graph-set notation, see: Bernstein et al. (1995).

Experimental top

A mixture of 2-ferrocenylidene-2(H)-indene-1,2-dione (20 mmol) and sarcosine (30 mmol) and acenapthylene-1,2-dione (30 mmol) were refluxed in benzene for 20 h and the solvent was removed under reduced pressure. The crude product was subjected to column chromatography to get the pure product. Chloroform and methanol (1:1) solvent mixture was used for the crystallization under slow evaporation method.

Refinement top

H atoms were positioned geometrically and refined using riding model, with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) for aromatic C—H, C—H = 0.98 Å and Uiso(H) = 1.2Ueq(C) for CH, C—H = 0.97 Å and Uiso(H) = 1.2Ueq(C) for CH2, and C—H = 0.96 Å and Uiso(H) = 1.5Ueq(C) for CH3. The components of the anisotropic displacement parameters in direction of the bond of C30, C31, C32 and C34 were restrained to be equal within an effective standard deviation of 0.001, using the DELU command in SHELXL97 (Sheldrick, 2008).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.
[Figure 2] Fig. 2. The packing of (I), viewed down the a axis. Hydrogen bonds are shown as dashed lines.
4'-Ferrocenyl-1'-methylacenapthylene-1-spiro-2'-pyrrolidine-3'- spiro-2''-indane-2,1'',3''(1H)-trione top
Crystal data top
[Fe(C5H5)(C29H20NO3)]F(000) = 1144
Mr = 551.40Dx = 1.438 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9589 reflections
a = 12.5511 (10) Åθ = 2.2–28.7°
b = 10.8633 (9) ŵ = 0.63 mm−1
c = 19.2099 (16) ÅT = 293 K
β = 103.432 (2)°Block, colourless
V = 2547.6 (4) Å30.25 × 0.20 × 0.15 mm
Z = 4
Data collection top
Bruker Kappa APEXII CCD
diffractometer		6771 independent reflections
Radiation source: fine-focus sealed tube5179 reflections with I > 2σ(I)
graphiteRint = 0.031
Detector resolution: 0 pixels mm-1θmax = 29.0°, θmin = 2.2°
φ and ω scansh = −17→17
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		k = −14→14
Tmin = 0.860, Tmax = 0.911l = −26→26
30734 measured reflections
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)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0687P)2 + 0.7386P]
where P = (Fo2 + 2Fc2)/3
6771 reflections(Δ/σ)max = 0.007
353 parametersΔρmax = 0.49 e Å−3
5 restraintsΔρmin = −0.42 e Å−3
Crystal data top
[Fe(C5H5)(C29H20NO3)]V = 2547.6 (4) Å3
Mr = 551.40Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.5511 (10) ŵ = 0.63 mm−1
b = 10.8633 (9) ÅT = 293 K
c = 19.2099 (16) Å0.25 × 0.20 × 0.15 mm
β = 103.432 (2)°
Data collection top
Bruker Kappa APEXII CCD
diffractometer		6771 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		5179 reflections with I > 2σ(I)
Tmin = 0.860, Tmax = 0.911Rint = 0.031
30734 measured reflectionsθmax = 29.0°
Refinement top
R[F2 > 2σ(F2)] = 0.040H-atom parameters constrained
wR(F2) = 0.124Δρmax = 0.49 e Å−3
S = 1.02Δρmin = −0.42 e Å−3
6771 reflectionsAbsolute structure: ?
353 parametersFlack parameter: ?
5 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.26851 (13)0.32057 (15)0.96632 (9)0.0302 (3)
C20.22528 (13)0.22624 (14)0.90588 (9)0.0292 (3)
C30.33376 (13)0.19055 (16)0.88341 (10)0.0340 (4)
H30.34930.25590.85200.041*
C40.42067 (15)0.1988 (2)0.95383 (11)0.0453 (5)
H4A0.44500.11710.97090.054*
H4B0.48350.24530.94720.054*
C50.29193 (15)0.45044 (16)0.93572 (10)0.0360 (4)
C60.23280 (15)0.54421 (16)0.96773 (10)0.0386 (4)
C70.23105 (19)0.67074 (18)0.96368 (12)0.0508 (5)
H70.26610.71230.93300.061*
C80.1748 (2)0.7348 (2)1.00733 (14)0.0597 (6)
H80.17270.82031.00520.072*
C90.12269 (18)0.6759 (2)1.05296 (13)0.0542 (5)
H90.08640.72221.08100.065*
C100.12281 (15)0.54626 (19)1.05833 (10)0.0414 (4)
C110.07709 (17)0.4733 (2)1.10488 (11)0.0476 (5)
H110.03690.51011.13430.057*
C120.09210 (17)0.3485 (2)1.10665 (10)0.0479 (5)
H120.06170.30201.13780.057*
C130.15220 (16)0.28747 (18)1.06292 (10)0.0418 (4)
H130.16280.20281.06640.050*
C140.19421 (13)0.35462 (15)1.01581 (9)0.0321 (3)
C150.17929 (15)0.48339 (15)1.01399 (10)0.0340 (4)
C160.13789 (14)0.27455 (16)0.84251 (9)0.0365 (4)
C170.04269 (13)0.19062 (16)0.82985 (9)0.0333 (3)
C18−0.05434 (16)0.1963 (2)0.77759 (11)0.0457 (5)
H18−0.06630.25770.74290.055*
C19−0.13250 (17)0.1074 (2)0.77898 (13)0.0557 (6)
H19−0.19780.10810.74410.067*
C20−0.11559 (18)0.0177 (2)0.83102 (14)0.0560 (6)
H20−0.1703−0.04010.83100.067*
C21−0.01942 (17)0.01133 (18)0.88323 (12)0.0459 (5)
H21−0.0084−0.04950.91820.055*
C220.06043 (13)0.09933 (15)0.88157 (9)0.0321 (3)
C230.16939 (13)0.11364 (14)0.93040 (9)0.0297 (3)
C240.44333 (17)0.3360 (2)1.05712 (11)0.0503 (5)
H24A0.47620.39741.03280.075*
H24B0.49960.28501.08540.075*
H24C0.40320.37541.08780.075*
C250.32820 (14)0.07159 (16)0.84323 (10)0.0343 (4)
C260.34818 (15)−0.05036 (17)0.87150 (11)0.0391 (4)
H260.3681−0.07140.91970.047*
C270.33237 (16)−0.13339 (19)0.81320 (12)0.0491 (5)
H270.3406−0.21840.81660.059*
C280.30209 (18)−0.0657 (2)0.74947 (12)0.0555 (6)
H280.2866−0.09810.70340.067*
C290.29919 (16)0.0608 (2)0.76739 (11)0.0460 (5)
H290.28140.12560.73510.055*
C300.5872 (2)0.0968 (3)0.8343 (2)0.0886 (8)
H300.59130.17090.85910.106*
C310.60864 (19)−0.0238 (4)0.86344 (15)0.0864 (8)
H310.6298−0.04500.91160.104*
C320.5917 (2)−0.1012 (3)0.8066 (3)0.0876 (9)
H320.6000−0.18630.80980.105*
C330.5625 (3)−0.0405 (5)0.7471 (2)0.0943 (11)
H330.5464−0.07560.70170.113*
C340.5589 (2)0.0793 (4)0.7605 (2)0.0915 (10)
H340.54050.14110.72640.110*
N10.36930 (11)0.26055 (14)1.00483 (8)0.0358 (3)
O10.14436 (15)0.36625 (16)0.80913 (10)0.0759 (6)
O20.20805 (11)0.04640 (12)0.97995 (7)0.0436 (3)
O30.35663 (13)0.46876 (13)0.89941 (8)0.0510 (4)
Fe10.45199 (2)−0.00912 (2)0.806961 (13)0.03531 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0306 (8)0.0266 (7)0.0349 (8)−0.0055 (6)0.0108 (6)−0.0020 (6)
C20.0278 (7)0.0257 (7)0.0342 (8)−0.0027 (6)0.0078 (6)0.0010 (6)
C30.0289 (8)0.0335 (8)0.0415 (9)−0.0044 (6)0.0117 (7)−0.0050 (7)
C40.0284 (8)0.0521 (11)0.0529 (11)−0.0009 (8)0.0045 (8)−0.0171 (9)
C50.0391 (9)0.0308 (8)0.0393 (9)−0.0104 (7)0.0116 (7)−0.0027 (7)
C60.0423 (10)0.0289 (8)0.0449 (10)−0.0046 (7)0.0108 (8)−0.0014 (7)
C70.0611 (13)0.0298 (9)0.0626 (13)−0.0047 (9)0.0169 (11)0.0026 (9)
C80.0671 (15)0.0317 (10)0.0778 (16)0.0063 (10)0.0115 (13)−0.0067 (10)
C90.0543 (12)0.0457 (11)0.0622 (13)0.0101 (10)0.0125 (11)−0.0164 (10)
C100.0364 (9)0.0442 (10)0.0423 (10)0.0023 (8)0.0066 (8)−0.0095 (8)
C110.0419 (10)0.0632 (13)0.0402 (10)−0.0003 (9)0.0149 (8)−0.0129 (9)
C120.0488 (11)0.0607 (13)0.0382 (10)−0.0118 (9)0.0185 (9)−0.0017 (9)
C130.0462 (10)0.0399 (10)0.0417 (10)−0.0075 (8)0.0150 (8)0.0011 (8)
C140.0306 (8)0.0330 (8)0.0334 (8)−0.0050 (6)0.0086 (7)−0.0032 (6)
C150.0339 (8)0.0328 (8)0.0348 (9)−0.0019 (7)0.0071 (7)−0.0031 (6)
C160.0365 (9)0.0344 (9)0.0380 (9)−0.0007 (7)0.0071 (7)0.0040 (7)
C170.0310 (8)0.0348 (8)0.0341 (8)0.0018 (7)0.0075 (7)−0.0043 (7)
C180.0399 (10)0.0514 (11)0.0414 (10)0.0067 (8)0.0004 (8)−0.0048 (9)
C190.0355 (10)0.0652 (14)0.0583 (13)−0.0017 (10)−0.0056 (9)−0.0146 (11)
C200.0367 (10)0.0562 (13)0.0714 (16)−0.0166 (9)0.0050 (10)−0.0085 (11)
C210.0401 (10)0.0406 (10)0.0562 (12)−0.0121 (8)0.0097 (9)−0.0005 (8)
C220.0296 (8)0.0305 (8)0.0362 (8)−0.0026 (6)0.0079 (7)−0.0049 (6)
C230.0296 (7)0.0246 (7)0.0353 (8)−0.0028 (6)0.0084 (6)−0.0017 (6)
C240.0435 (11)0.0518 (11)0.0492 (11)−0.0111 (9)−0.0020 (9)−0.0137 (9)
C250.0280 (8)0.0350 (8)0.0391 (9)0.0007 (7)0.0064 (7)−0.0053 (7)
C260.0355 (9)0.0358 (9)0.0488 (10)−0.0018 (7)0.0155 (8)−0.0017 (8)
C270.0401 (10)0.0396 (10)0.0680 (14)−0.0024 (8)0.0135 (10)−0.0158 (10)
C280.0451 (11)0.0648 (14)0.0506 (12)0.0027 (10)−0.0008 (9)−0.0256 (11)
C290.0389 (10)0.0539 (12)0.0401 (10)0.0084 (9)−0.0010 (8)−0.0064 (9)
C300.0441 (13)0.0844 (13)0.148 (2)−0.0253 (12)0.0450 (16)−0.0605 (15)
C310.0293 (10)0.179 (2)0.0490 (12)−0.0047 (16)0.0056 (10)0.0330 (12)
C320.0522 (15)0.0571 (12)0.166 (3)0.0133 (12)0.0508 (19)0.0076 (16)
C330.077 (2)0.141 (3)0.081 (2)−0.015 (2)0.0515 (19)−0.029 (2)
C340.0549 (15)0.114 (3)0.1110 (17)0.0018 (16)0.0296 (16)0.0689 (17)
N10.0302 (7)0.0357 (7)0.0395 (8)−0.0041 (6)0.0041 (6)−0.0068 (6)
O10.0702 (11)0.0640 (11)0.0797 (12)−0.0189 (9)−0.0106 (9)0.0421 (9)
O20.0469 (7)0.0342 (6)0.0447 (7)−0.0056 (6)0.0003 (6)0.0102 (6)
O30.0604 (9)0.0424 (7)0.0608 (9)−0.0197 (7)0.0351 (8)−0.0063 (6)
Fe10.03380 (15)0.04039 (16)0.03252 (15)0.00359 (10)0.00929 (10)−0.00137 (10)
Geometric parameters (Å, °) top
C1—N11.462 (2)C20—C211.380 (3)
C1—C141.524 (2)C20—H200.9300
C1—C21.549 (2)C21—C221.391 (2)
C1—C51.582 (2)C21—H210.9300
C2—C161.530 (2)C22—C231.476 (2)
C2—C231.537 (2)C23—O21.209 (2)
C2—C31.569 (2)C24—N11.453 (2)
C3—C251.499 (2)C24—H24A0.9600
C3—C41.530 (2)C24—H24B0.9600
C3—H30.9800C24—H24C0.9600
C4—N11.456 (2)C25—C291.422 (3)
C4—H4A0.9700C25—C261.432 (3)
C4—H4B0.9700C25—Fe12.0424 (17)
C5—O31.204 (2)C26—C271.416 (3)
C5—C61.476 (3)C26—Fe12.0459 (19)
C6—C71.377 (3)C26—H260.9300
C6—C151.398 (3)C27—C281.403 (3)
C7—C81.401 (3)C27—Fe12.043 (2)
C7—H70.9300C27—H270.9300
C8—C91.368 (3)C28—C291.419 (3)
C8—H80.9300C28—Fe12.042 (2)
C9—C101.412 (3)C28—H280.9300
C9—H90.9300C29—Fe12.0386 (19)
C10—C151.405 (3)C29—H290.9300
C10—C111.412 (3)C30—C341.391 (5)
C11—C121.368 (3)C30—C311.426 (5)
C11—H110.9300C30—Fe12.017 (2)
C12—C131.417 (3)C30—H300.9300
C12—H120.9300C31—C321.356 (5)
C13—C141.361 (2)C31—Fe12.019 (2)
C13—H130.9300C31—H310.9300
C14—C151.411 (2)C32—C331.296 (5)
C16—O11.198 (2)C32—Fe12.021 (2)
C16—C171.478 (2)C32—H320.9300
C17—C221.385 (2)C33—C341.330 (5)
C17—C181.388 (2)C33—Fe12.026 (3)
C18—C191.381 (3)C33—H330.9300
C18—H180.9300C34—Fe12.018 (3)
C19—C201.377 (3)C34—H340.9300
C19—H190.9300
N1—C1—C14112.06 (14)Fe1—C26—H26126.6
N1—C1—C2101.27 (13)C28—C27—C26108.42 (18)
C14—C1—C2118.01 (13)C28—C27—Fe169.89 (13)
N1—C1—C5111.84 (13)C26—C27—Fe169.85 (11)
C14—C1—C5102.05 (13)C28—C27—H27125.8
C2—C1—C5111.98 (13)C26—C27—H27125.8
C16—C2—C23102.89 (13)Fe1—C27—H27126.1
C16—C2—C1115.53 (14)C27—C28—C29108.25 (18)
C23—C2—C1113.69 (13)C27—C28—Fe169.95 (12)
C16—C2—C3111.93 (14)C29—C28—Fe169.51 (11)
C23—C2—C3111.99 (13)C27—C28—H28125.9
C1—C2—C3101.21 (12)C29—C28—H28125.9
C25—C3—C4116.36 (15)Fe1—C28—H28126.2
C25—C3—C2114.52 (13)C28—C29—C25108.25 (19)
C4—C3—C2103.20 (14)C28—C29—Fe169.80 (11)
C25—C3—H3107.4C25—C29—Fe169.75 (10)
C4—C3—H3107.4C28—C29—H29125.9
C2—C3—H3107.4C25—C29—H29125.9
N1—C4—C3106.59 (14)Fe1—C29—H29126.2
N1—C4—H4A110.4C34—C30—C31104.7 (3)
C3—C4—H4A110.4C34—C30—Fe169.89 (16)
N1—C4—H4B110.4C31—C30—Fe169.39 (15)
C3—C4—H4B110.4C34—C30—H30127.6
H4A—C4—H4B108.6C31—C30—H30127.6
O3—C5—C6126.83 (17)Fe1—C30—H30124.7
O3—C5—C1124.85 (17)C32—C31—C30105.9 (3)
C6—C5—C1107.81 (14)C32—C31—Fe170.46 (16)
C7—C6—C15120.27 (19)C30—C31—Fe169.22 (14)
C7—C6—C5131.96 (19)C32—C31—H31127.1
C15—C6—C5107.51 (15)C30—C31—H31127.1
C6—C7—C8117.8 (2)Fe1—C31—H31124.9
C6—C7—H7121.1C33—C32—C31110.7 (3)
C8—C7—H7121.1C33—C32—Fe171.53 (18)
C9—C8—C7122.3 (2)C31—C32—Fe170.32 (16)
C9—C8—H8118.9C33—C32—H32124.6
C7—C8—H8118.9C31—C32—H32124.6
C8—C9—C10121.4 (2)Fe1—C32—H32125.1
C8—C9—H9119.3C32—C33—C34110.0 (3)
C10—C9—H9119.3C32—C33—Fe171.11 (17)
C15—C10—C9115.6 (2)C34—C33—Fe170.49 (18)
C15—C10—C11116.59 (18)C32—C33—H33125.0
C9—C10—C11127.7 (2)C34—C33—H33125.0
C12—C11—C10119.84 (19)Fe1—C33—H33125.0
C12—C11—H11120.1C33—C34—C30108.7 (3)
C10—C11—H11120.1C33—C34—Fe171.12 (17)
C11—C12—C13122.57 (19)C30—C34—Fe169.79 (16)
C11—C12—H12118.7C33—C34—H34125.7
C13—C12—H12118.7C30—C34—H34125.7
C14—C13—C12119.02 (18)Fe1—C34—H34125.0
C14—C13—H13120.5C24—N1—C4114.41 (15)
C12—C13—H13120.5C24—N1—C1115.95 (15)
C13—C14—C15118.58 (17)C4—N1—C1109.36 (14)
C13—C14—C1132.28 (16)C30—Fe1—C3440.32 (15)
C15—C14—C1108.80 (14)C30—Fe1—C3141.39 (14)
C6—C15—C10122.69 (17)C34—Fe1—C3167.09 (12)
C6—C15—C14113.81 (16)C30—Fe1—C3266.72 (13)
C10—C15—C14123.34 (18)C34—Fe1—C3264.36 (14)
O1—C16—C17125.32 (17)C31—Fe1—C3239.22 (14)
O1—C16—C2125.89 (17)C30—Fe1—C3366.29 (14)
C17—C16—C2108.79 (14)C34—Fe1—C3338.39 (16)
C22—C17—C18121.22 (17)C31—Fe1—C3365.30 (14)
C22—C17—C16109.57 (15)C32—Fe1—C3337.36 (15)
C18—C17—C16129.18 (17)C30—Fe1—C29123.12 (12)
C19—C18—C17117.58 (19)C34—Fe1—C29108.80 (11)
C19—C18—H18121.2C31—Fe1—C29160.75 (14)
C17—C18—H18121.2C32—Fe1—C29157.71 (15)
C20—C19—C18121.23 (19)C33—Fe1—C29124.05 (14)
C20—C19—H19119.4C30—Fe1—C25109.11 (9)
C18—C19—H19119.4C34—Fe1—C25125.66 (14)
C19—C20—C21121.63 (19)C31—Fe1—C25125.00 (11)
C19—C20—H20119.2C32—Fe1—C25160.66 (14)
C21—C20—H20119.2C33—Fe1—C25160.29 (15)
C20—C21—C22117.52 (19)C29—Fe1—C2540.79 (7)
C20—C21—H21121.2C30—Fe1—C28157.86 (15)
C22—C21—H21121.2C34—Fe1—C28121.85 (13)
C17—C22—C21120.81 (17)C31—Fe1—C28157.88 (15)
C17—C22—C23110.57 (14)C32—Fe1—C28122.70 (13)
C21—C22—C23128.61 (17)C33—Fe1—C28107.98 (12)
O2—C23—C22125.46 (15)C29—Fe1—C2840.70 (9)
O2—C23—C2126.44 (15)C25—Fe1—C2868.61 (8)
C22—C23—C2108.08 (13)C30—Fe1—C27161.32 (14)
N1—C24—H24A109.5C34—Fe1—C27155.96 (15)
N1—C24—H24B109.5C31—Fe1—C27123.59 (12)
H24A—C24—H24B109.5C32—Fe1—C27108.86 (11)
N1—C24—H24C109.5C33—Fe1—C27122.10 (14)
H24A—C24—H24C109.5C29—Fe1—C2768.14 (9)
H24B—C24—H24C109.5C25—Fe1—C2768.65 (7)
C29—C25—C26107.04 (16)C28—Fe1—C2740.16 (10)
C29—C25—C3124.67 (17)C30—Fe1—C26125.69 (12)
C26—C25—C3128.28 (17)C34—Fe1—C26162.60 (15)
C29—C25—Fe169.46 (11)C31—Fe1—C26109.55 (9)
C26—C25—Fe169.64 (10)C32—Fe1—C26124.70 (13)
C3—C25—Fe1126.71 (12)C33—Fe1—C26157.45 (16)
C27—C26—C25108.03 (18)C29—Fe1—C2668.36 (8)
C27—C26—Fe169.64 (12)C25—Fe1—C2640.99 (7)
C25—C26—Fe169.37 (10)C28—Fe1—C2668.00 (9)
C27—C26—H26126.0C27—Fe1—C2640.51 (8)
C25—C26—H26126.0
N1—C1—C2—C16−163.27 (14)C33—C34—Fe1—C3178.6 (2)
C14—C1—C2—C1674.06 (19)C30—C34—Fe1—C31−40.5 (2)
C5—C1—C2—C16−43.96 (19)C33—C34—Fe1—C3235.5 (2)
N1—C1—C2—C2378.07 (15)C30—C34—Fe1—C32−83.6 (2)
C14—C1—C2—C23−44.6 (2)C30—C34—Fe1—C33−119.1 (3)
C5—C1—C2—C23−162.62 (13)C33—C34—Fe1—C29−121.5 (2)
N1—C1—C2—C3−42.18 (15)C30—C34—Fe1—C29119.39 (19)
C14—C1—C2—C3−164.85 (14)C33—C34—Fe1—C25−163.8 (2)
C5—C1—C2—C377.13 (16)C30—C34—Fe1—C2577.1 (2)
C16—C2—C3—C25−75.73 (18)C33—C34—Fe1—C28−78.5 (2)
C23—C2—C3—C2539.2 (2)C30—C34—Fe1—C28162.39 (18)
C1—C2—C3—C25160.67 (14)C33—C34—Fe1—C27−43.2 (4)
C16—C2—C3—C4156.81 (15)C30—C34—Fe1—C27−162.3 (2)
C23—C2—C3—C4−88.24 (16)C33—C34—Fe1—C26161.0 (3)
C1—C2—C3—C433.21 (16)C30—C34—Fe1—C2641.9 (4)
C25—C3—C4—N1−138.43 (16)C32—C31—Fe1—C30−116.4 (3)
C2—C3—C4—N1−12.14 (19)C32—C31—Fe1—C34−77.0 (2)
N1—C1—C5—O352.2 (2)C30—C31—Fe1—C3439.4 (2)
C14—C1—C5—O3172.19 (18)C30—C31—Fe1—C32116.4 (3)
C2—C1—C5—O3−60.7 (2)C32—C31—Fe1—C33−34.9 (2)
N1—C1—C5—C6−120.07 (16)C30—C31—Fe1—C3381.5 (2)
C14—C1—C5—C6−0.12 (18)C32—C31—Fe1—C29−158.4 (3)
C2—C1—C5—C6127.04 (15)C30—C31—Fe1—C29−42.0 (4)
O3—C5—C6—C72.6 (4)C32—C31—Fe1—C25164.54 (18)
C1—C5—C6—C7174.7 (2)C30—C31—Fe1—C25−79.04 (19)
O3—C5—C6—C15−171.30 (19)C32—C31—Fe1—C2841.8 (3)
C1—C5—C6—C150.8 (2)C30—C31—Fe1—C28158.2 (3)
C15—C6—C7—C80.3 (3)C32—C31—Fe1—C2778.5 (2)
C5—C6—C7—C8−173.0 (2)C30—C31—Fe1—C27−165.12 (16)
C6—C7—C8—C90.1 (4)C32—C31—Fe1—C26121.36 (19)
C7—C8—C9—C10−0.1 (4)C30—C31—Fe1—C26−122.23 (17)
C8—C9—C10—C15−0.1 (3)C33—C32—Fe1—C30−80.9 (3)
C8—C9—C10—C11177.0 (2)C31—C32—Fe1—C3040.14 (19)
C15—C10—C11—C122.1 (3)C33—C32—Fe1—C34−36.5 (2)
C9—C10—C11—C12−175.0 (2)C31—C32—Fe1—C3484.6 (2)
C10—C11—C12—C13−0.3 (3)C33—C32—Fe1—C31−121.1 (3)
C11—C12—C13—C14−1.9 (3)C31—C32—Fe1—C33121.1 (3)
C12—C13—C14—C152.1 (3)C33—C32—Fe1—C2940.3 (4)
C12—C13—C14—C1174.51 (17)C31—C32—Fe1—C29161.4 (2)
N1—C1—C14—C13−53.8 (2)C33—C32—Fe1—C25−162.3 (3)
C2—C1—C14—C1363.2 (3)C31—C32—Fe1—C25−41.2 (4)
C5—C1—C14—C13−173.61 (18)C33—C32—Fe1—C2876.3 (3)
N1—C1—C14—C15119.20 (15)C31—C32—Fe1—C28−162.64 (18)
C2—C1—C14—C15−123.78 (16)C33—C32—Fe1—C27118.5 (2)
C5—C1—C14—C15−0.61 (17)C31—C32—Fe1—C27−120.40 (19)
C7—C6—C15—C10−0.5 (3)C33—C32—Fe1—C26160.8 (2)
C5—C6—C15—C10174.26 (17)C31—C32—Fe1—C26−78.2 (2)
C7—C6—C15—C14−176.06 (18)C32—C33—Fe1—C3082.2 (3)
C5—C6—C15—C14−1.3 (2)C34—C33—Fe1—C30−38.1 (2)
C9—C10—C15—C60.4 (3)C32—C33—Fe1—C34120.3 (3)
C11—C10—C15—C6−177.01 (18)C32—C33—Fe1—C3136.6 (2)
C9—C10—C15—C14175.54 (18)C34—C33—Fe1—C31−83.7 (2)
C11—C10—C15—C14−1.9 (3)C34—C33—Fe1—C32−120.3 (3)
C13—C14—C15—C6175.32 (17)C32—C33—Fe1—C29−162.8 (2)
C1—C14—C15—C61.2 (2)C34—C33—Fe1—C2976.9 (2)
C13—C14—C15—C10−0.2 (3)C32—C33—Fe1—C25162.6 (3)
C1—C14—C15—C10−174.29 (16)C34—C33—Fe1—C2542.3 (4)
C23—C2—C16—O1175.8 (2)C32—C33—Fe1—C28−120.7 (2)
C1—C2—C16—O151.3 (3)C34—C33—Fe1—C28118.9 (2)
C3—C2—C16—O1−63.8 (3)C32—C33—Fe1—C27−78.9 (3)
C23—C2—C16—C17−3.16 (18)C34—C33—Fe1—C27160.79 (19)
C1—C2—C16—C17−127.64 (15)C32—C33—Fe1—C26−44.9 (4)
C3—C2—C16—C17117.25 (15)C34—C33—Fe1—C26−165.3 (2)
O1—C16—C17—C22−175.7 (2)C28—C29—Fe1—C30159.64 (17)
C2—C16—C17—C223.26 (19)C25—C29—Fe1—C30−80.92 (17)
O1—C16—C17—C182.4 (3)C28—C29—Fe1—C34117.3 (2)
C2—C16—C17—C18−178.70 (17)C25—C29—Fe1—C34−123.24 (18)
C22—C17—C18—C19−0.1 (3)C28—C29—Fe1—C31−168.5 (3)
C16—C17—C18—C19−177.94 (19)C25—C29—Fe1—C31−49.0 (3)
C17—C18—C19—C201.1 (3)C28—C29—Fe1—C3249.3 (3)
C18—C19—C20—C21−1.1 (4)C25—C29—Fe1—C32168.8 (3)
C19—C20—C21—C220.1 (3)C28—C29—Fe1—C3377.6 (2)
C18—C17—C22—C21−0.9 (3)C25—C29—Fe1—C33−162.95 (17)
C16—C17—C22—C21177.32 (17)C28—C29—Fe1—C25−119.44 (19)
C18—C17—C22—C23179.88 (16)C25—C29—Fe1—C28119.44 (19)
C16—C17—C22—C23−1.90 (19)C28—C29—Fe1—C27−37.22 (14)
C20—C21—C22—C170.9 (3)C25—C29—Fe1—C2782.22 (12)
C20—C21—C22—C23179.97 (19)C28—C29—Fe1—C26−80.99 (14)
C17—C22—C23—O2−178.74 (17)C25—C29—Fe1—C2638.45 (11)
C21—C22—C23—O22.1 (3)C29—C25—Fe1—C30118.92 (17)
C17—C22—C23—C2−0.19 (18)C26—C25—Fe1—C30−122.85 (17)
C21—C22—C23—C2−179.33 (18)C3—C25—Fe1—C300.3 (2)
C16—C2—C23—O2−179.41 (17)C29—C25—Fe1—C3477.04 (18)
C1—C2—C23—O2−53.7 (2)C26—C25—Fe1—C34−164.74 (16)
C3—C2—C23—O260.2 (2)C3—C25—Fe1—C34−41.5 (2)
C16—C2—C23—C222.06 (17)C29—C25—Fe1—C31162.31 (16)
C1—C2—C23—C22127.74 (14)C26—C25—Fe1—C31−79.46 (17)
C3—C2—C23—C22−118.31 (15)C3—C25—Fe1—C3143.7 (2)
C4—C3—C25—C29−147.00 (18)C29—C25—Fe1—C32−167.1 (3)
C2—C3—C25—C2992.6 (2)C26—C25—Fe1—C32−48.9 (3)
C4—C3—C25—C2634.1 (3)C3—C25—Fe1—C3274.3 (4)
C2—C3—C25—C26−86.3 (2)C29—C25—Fe1—C3346.1 (4)
C4—C3—C25—Fe1−57.9 (2)C26—C25—Fe1—C33164.3 (3)
C2—C3—C25—Fe1−178.34 (12)C3—C25—Fe1—C33−72.5 (4)
C29—C25—C26—C270.6 (2)C26—C25—Fe1—C29118.22 (16)
C3—C25—C26—C27179.61 (17)C3—C25—Fe1—C29−118.6 (2)
Fe1—C25—C26—C27−59.11 (13)C29—C25—Fe1—C28−37.58 (13)
C29—C25—C26—Fe159.66 (13)C26—C25—Fe1—C2880.64 (13)
C3—C25—C26—Fe1−121.29 (17)C3—C25—Fe1—C28−156.16 (19)
C25—C26—C27—C28−0.5 (2)C29—C25—Fe1—C27−80.85 (13)
Fe1—C26—C27—C28−59.45 (15)C26—C25—Fe1—C2737.37 (12)
C25—C26—C27—Fe158.94 (12)C3—C25—Fe1—C27160.57 (18)
C26—C27—C28—C290.3 (2)C29—C25—Fe1—C26−118.22 (16)
Fe1—C27—C28—C29−59.15 (15)C3—C25—Fe1—C26123.2 (2)
C26—C27—C28—Fe159.43 (14)C27—C28—Fe1—C30−170.1 (2)
C27—C28—C29—C250.1 (2)C29—C28—Fe1—C30−50.6 (3)
Fe1—C28—C29—C25−59.35 (13)C27—C28—Fe1—C34158.58 (18)
C27—C28—C29—Fe159.42 (15)C29—C28—Fe1—C34−81.9 (2)
C26—C25—C29—C28−0.4 (2)C27—C28—Fe1—C3150.4 (3)
C3—C25—C29—C28−179.48 (17)C29—C28—Fe1—C31169.9 (2)
Fe1—C25—C29—C2859.38 (14)C27—C28—Fe1—C3280.5 (2)
C26—C25—C29—Fe1−59.77 (12)C29—C28—Fe1—C32−160.01 (17)
C3—C25—C29—Fe1121.14 (17)C27—C28—Fe1—C33118.80 (19)
C34—C30—C31—C32−0.1 (3)C29—C28—Fe1—C33−121.71 (19)
Fe1—C30—C31—C3261.34 (18)C27—C28—Fe1—C29−119.49 (18)
C34—C30—C31—Fe1−61.40 (18)C27—C28—Fe1—C25−81.83 (12)
C30—C31—C32—C33−0.2 (3)C29—C28—Fe1—C2537.66 (12)
Fe1—C31—C32—C3360.3 (2)C29—C28—Fe1—C27119.49 (18)
C30—C31—C32—Fe1−60.51 (17)C27—C28—Fe1—C26−37.56 (12)
C31—C32—C33—C340.4 (4)C29—C28—Fe1—C2681.93 (13)
Fe1—C32—C33—C3460.0 (2)C28—C27—Fe1—C30168.4 (3)
C31—C32—C33—Fe1−59.6 (2)C26—C27—Fe1—C3048.8 (3)
C32—C33—C34—C30−0.4 (4)C28—C27—Fe1—C34−49.6 (3)
Fe1—C33—C34—C3059.9 (2)C26—C27—Fe1—C34−169.1 (2)
C32—C33—C34—Fe1−60.4 (2)C28—C27—Fe1—C31−159.61 (16)
C31—C30—C34—C330.3 (3)C26—C27—Fe1—C3180.86 (18)
Fe1—C30—C34—C33−60.8 (2)C28—C27—Fe1—C32−118.71 (18)
C31—C30—C34—Fe161.06 (17)C26—C27—Fe1—C32121.76 (18)
C3—C4—N1—C24−147.53 (17)C28—C27—Fe1—C33−79.7 (2)
C3—C4—N1—C1−15.5 (2)C26—C27—Fe1—C33160.75 (18)
C14—C1—N1—C24−65.40 (19)C28—C27—Fe1—C2937.70 (12)
C2—C1—N1—C24167.91 (15)C26—C27—Fe1—C29−81.83 (13)
C5—C1—N1—C2448.5 (2)C28—C27—Fe1—C2581.72 (13)
C14—C1—N1—C4163.43 (14)C26—C27—Fe1—C25−37.81 (11)
C2—C1—N1—C436.75 (17)C26—C27—Fe1—C28−119.53 (17)
C5—C1—N1—C4−82.66 (17)C28—C27—Fe1—C26119.53 (17)
C31—C30—Fe1—C34−115.3 (3)C27—C26—Fe1—C30−162.73 (17)
C34—C30—Fe1—C31115.3 (3)C25—C26—Fe1—C3077.76 (17)
C34—C30—Fe1—C3277.2 (2)C27—C26—Fe1—C34165.1 (3)
C31—C30—Fe1—C32−38.06 (19)C25—C26—Fe1—C3445.6 (4)
C34—C30—Fe1—C3336.4 (2)C27—C26—Fe1—C31−119.22 (18)
C31—C30—Fe1—C33−78.9 (2)C25—C26—Fe1—C31121.28 (16)
C34—C30—Fe1—C29−80.0 (2)C27—C26—Fe1—C32−78.16 (19)
C31—C30—Fe1—C29164.72 (16)C25—C26—Fe1—C32162.34 (16)
C34—C30—Fe1—C25−123.0 (2)C27—C26—Fe1—C33−46.7 (3)
C31—C30—Fe1—C25121.67 (17)C25—C26—Fe1—C33−166.2 (3)
C34—C30—Fe1—C28−43.0 (3)C27—C26—Fe1—C2981.24 (13)
C31—C30—Fe1—C28−158.3 (2)C25—C26—Fe1—C29−38.26 (11)
C34—C30—Fe1—C27157.2 (3)C27—C26—Fe1—C25119.50 (16)
C31—C30—Fe1—C2741.9 (4)C27—C26—Fe1—C2837.25 (13)
C34—C30—Fe1—C26−165.77 (18)C25—C26—Fe1—C28−82.26 (12)
C31—C30—Fe1—C2678.94 (19)C25—C26—Fe1—C27−119.50 (16)
C33—C34—Fe1—C30119.1 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O30.982.483.045 (2)116
C13—H13···O20.932.533.226 (2)132
C8—H8···O2i0.932.563.465 (6)164
Symmetry codes: (i) x, y+1, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O30.982.483.045 (2)116
C13—H13···O20.932.533.226 (2)132
C8—H8···O2i0.932.563.465 (6)164
Symmetry codes: (i) x, y+1, z.
Acknowledgements top

BG thanks AMET University management, India, for their kind support and SAIF, IITMadras, India, for the data collection.

references
References top

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.

Biot, C., Dessolin, J., Richard, I. & Dive, D. (2004). J. Organomet. Chem. 689, 4678–4682.

Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Fouda, M. F. R., Abd-Elzaher, M. M., Abdelsamaia, R. A. & Labib, A. A. (2007). Appl. Organomet. Chem. 21, 613–625.

Jaouen, G., Top, S., Vessireres, A., Leclercq, G., Vaissermann, J. & McGlinchey, M. J. (2004). Curr. Med. Chem. 11, 2505–2517.

Johnson, J. J. & Sames, D. (2000). J. Am. Chem. Soc. 122, 6321–6322.

Kamala, E. T. S., Nirmala, S., Sudha, L., Kathiravan, S. & Raghunathan, R. (2009). Acta Cryst. E65, m687–m688.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Spek, A. L. (2009). Acta Cryst. D65, 148–155.

Stalin Elanchezhian, V., Kandaswamy, M. & Ponnuswamy, M. N. (2008). Acta Cryst. E64, m265.