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

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ISSN: 2056-9890

6-Ferrocenoyl-7-(4-fluoro­phen­yl)spiro­[hexa­hydro­pyrrolo­[1,2-c][1,3]thia­zole-5,11′-indeno­[1,2-b]quinoxaline]

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

(Received 7 August 2013; accepted 12 August 2013; online 17 August 2013)

In the title compound, [Fe(C5H5)(C32H23FN3OS)], both the thia­zolidine ring and the pyrrolidine ring adopt a twist conformation on the N—C(H) bridging bond. Their mean planes are inclined to one another by 10.05 (10)°, and they make dihedral angles of 82.09 (10) and 89.67 (11)°, respectively, with the cyclo­pentane ring. The F atom deviates by −0.0238 (2) Å from the benzene ring to which it is attached. In the crystal, mol­ecules are linked by a pair of C—H⋯O hydrogen bonds, forming inversion dimers.

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 a related structure, see: Vijayakumar et al. (2012[Vijayakumar, B., Gavaskar, D., Srinivasan, T., Raghunathan, R. & Velmurugan, D. (2012). Acta Cryst. E68, m1382-m1383.]).

[Scheme 1]

Experimental

Crystal data
  • [Fe(C5H5)(C32H23FN3OS)]

  • Mr = 637.53

  • Triclinic, [P \overline 1]

  • a = 8.7097 (2) Å

  • b = 12.6456 (3) Å

  • c = 13.5477 (4) Å

  • α = 83.865 (1)°

  • β = 79.008 (1)°

  • γ = 86.776 (1)°

  • V = 1455.39 (6) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.63 mm−1

  • T = 293 K

  • 0.30 × 0.25 × 0.20 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 = 0.833, Tmax = 0.884

  • 22064 measured reflections

  • 5966 independent reflections

  • 5126 reflections with I > 2σ(I)

  • Rint = 0.022

Refinement
  • R[F2 > 2σ(F2)] = 0.035

  • wR(F2) = 0.097

  • S = 1.06

  • 5966 reflections

  • 397 parameters

  • H-atom parameters constrained

  • Δρmax = 0.33 e Å−3

  • Δρmin = −0.34 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C25—H25⋯O1i 0.93 2.54 3.212 (2) 129
Symmetry code: (i) -x+1, -y+1, -z+1.

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 for Windows (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, such as antimalarial, antifungal (Biot et al., 2004), antitumor (Jaouen et al., 2004), and antibacterial (Fouda et al., 2007). Against this background, and in order to gain information on the molecular conformations and crystal packing, we report herein on the synthesis and crystal structure of the title compound.

In the title compound, Fig. 1, both the thiazolidine ring and the pyrrolidine ring adopt a twist conformation on bond N3-C18. The thiazolidine ring (S1/N3/C18-C20) mean plane makes a dihedral angle of 10.05 (10)° with the pyrrolidine ring (N3/C15-C18) mean plane, it also makes a dihedral angle of 82.09 (10)° with the cyclopentane ring (C7-C9/C14/C15) which shows that they are almost perpendicular to each other. The pyrrolidine ring mean plane makes a dihedral angle of 89.67 (11)° with the cyclopentane ring which shows they too are almost orthogonal to each other. The fluorine atom F1 attached with the phenyl ring (C21-C26) deviates by -0.0238 (2)Å.

In the crystal, molecules are linked by a pair of C-H···O hydrogen bonds forming inversion dimers (Table 1 and Fig. 2).

Related literature top

For the biological activity of ferrocene derivatives, see: Jaouen et al. (2004); Biot et al. (2004); Fouda et al. (2007). For a related structure, see: Vijayakumar et al. (2012).

Experimental top

Ninhydrin (1 mmol) and 1, 2-phenylenediamine (1 mmol) were mixed and stirred with 10 ml of methanol for 10 min. To this mixture 1 mmol of thioproline and 1-ferrocenyl-3-(4-fluoro) phenyl prop-2-ene-1-one dipolarophile were added and the mixture 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 with a 4:1 ratio of petroleum ether and ethyl acetate. Finally, single crystals suitable for the X-ray diffraction were obtained by slow evaporation of the solvent at room temperature.

Refinement top

Hydrogen atoms were placed in calculated positions with C—H ranging from 0.93 - 0.98 Å and refined using the riding model approximation with Uiso(H) = 1.2Ueq(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 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. The crystal packing of the title compound viewed along the a axis. The C-H···O hydrogen bonds are shown as dashed lines (see Table 1 for details; H-atoms not involved in hydrogen bonding have been omitted for clarity).
6-Ferrocenoyl-7-(4-fluorophenyl)spiro[hexahydropyrrolo[1,2-c][1,3]thiazole-5,11'-indeno[1,2-b]quinoxaline] top
Crystal data top
[Fe(C5H5)(C32H23FN3OS)]Z = 2
Mr = 637.53F(000) = 660
Triclinic, P1Dx = 1.455 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.7097 (2) ÅCell parameters from 5966 reflections
b = 12.6456 (3) Åθ = 1.5–26.5°
c = 13.5477 (4) ŵ = 0.63 mm1
α = 83.865 (1)°T = 293 K
β = 79.008 (1)°Block, colourless
γ = 86.776 (1)°0.30 × 0.25 × 0.20 mm
V = 1455.39 (6) Å3
Data collection top
Bruker SMART APEXII area-detector
diffractometer
5966 independent reflections
Radiation source: fine-focus sealed tube5126 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
ω and ϕ scansθmax = 26.5°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
h = 1010
Tmin = 0.833, Tmax = 0.884k = 1515
22064 measured reflectionsl = 1615
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)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0495P)2 + 0.4866P]
where P = (Fo2 + 2Fc2)/3
5966 reflections(Δ/σ)max = 0.001
397 parametersΔρmax = 0.33 e Å3
0 restraintsΔρmin = 0.34 e Å3
Crystal data top
[Fe(C5H5)(C32H23FN3OS)]γ = 86.776 (1)°
Mr = 637.53V = 1455.39 (6) Å3
Triclinic, P1Z = 2
a = 8.7097 (2) ÅMo Kα radiation
b = 12.6456 (3) ŵ = 0.63 mm1
c = 13.5477 (4) ÅT = 293 K
α = 83.865 (1)°0.30 × 0.25 × 0.20 mm
β = 79.008 (1)°
Data collection top
Bruker SMART APEXII area-detector
diffractometer
5966 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
5126 reflections with I > 2σ(I)
Tmin = 0.833, Tmax = 0.884Rint = 0.022
22064 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0350 restraints
wR(F2) = 0.097H-atom parameters constrained
S = 1.06Δρmax = 0.33 e Å3
5966 reflectionsΔρmin = 0.34 e Å3
397 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
C10.2262 (2)0.05617 (15)0.90688 (16)0.0455 (5)
C20.1056 (3)0.12677 (18)0.9492 (2)0.0610 (6)
H20.05860.12631.01680.073*
C30.0579 (3)0.19557 (19)0.8913 (2)0.0676 (7)
H30.02360.24040.91950.081*
C40.1296 (3)0.19979 (19)0.7904 (2)0.0645 (6)
H40.09750.24860.75250.077*
C50.2470 (3)0.13261 (17)0.74675 (18)0.0545 (5)
H50.29490.13630.67970.065*
C60.2949 (2)0.05802 (14)0.80348 (15)0.0422 (4)
C70.4407 (2)0.08107 (14)0.81340 (13)0.0356 (4)
C80.3754 (2)0.08071 (14)0.91808 (14)0.0390 (4)
C90.4426 (2)0.16713 (15)0.95772 (14)0.0402 (4)
C100.4181 (3)0.19841 (19)1.05442 (16)0.0550 (5)
H100.34980.16251.10690.066*
C110.4977 (3)0.2844 (2)1.07091 (18)0.0645 (6)
H110.48240.30691.13530.077*
C120.5997 (3)0.3376 (2)0.99315 (18)0.0595 (6)
H120.65220.39511.00610.071*
C130.6249 (2)0.30632 (17)0.89627 (16)0.0476 (5)
H130.69460.34170.84430.057*
C140.5441 (2)0.22119 (15)0.87846 (14)0.0376 (4)
C150.5453 (2)0.17673 (14)0.77843 (13)0.0347 (4)
C160.4710 (2)0.25222 (13)0.69710 (13)0.0323 (4)
H160.36940.22490.69340.039*
C170.5827 (2)0.24183 (14)0.59451 (13)0.0346 (4)
H170.64620.30510.57820.042*
C180.6895 (2)0.14625 (14)0.61692 (14)0.0368 (4)
H180.63870.08000.61280.044*
C190.8574 (2)0.14255 (17)0.55980 (16)0.0468 (5)
H19A0.89690.21370.54260.056*
H19B0.86510.10820.49830.056*
C200.8016 (2)0.06956 (18)0.75419 (16)0.0507 (5)
H20A0.74720.00320.76700.061*
H20B0.83730.08360.81500.061*
C210.4942 (2)0.23492 (14)0.50971 (13)0.0355 (4)
C220.3981 (2)0.14988 (15)0.51023 (15)0.0432 (4)
H220.39420.09390.56100.052*
C230.3088 (2)0.14764 (16)0.43653 (16)0.0472 (5)
H230.24470.09110.43720.057*
C240.3172 (2)0.23083 (17)0.36242 (15)0.0452 (5)
C250.4097 (2)0.31543 (16)0.35810 (15)0.0443 (4)
H250.41310.37070.30670.053*
C260.4984 (2)0.31637 (14)0.43271 (14)0.0394 (4)
H260.56240.37320.43090.047*
C270.4460 (2)0.36722 (14)0.72321 (14)0.0350 (4)
C280.3001 (2)0.39424 (14)0.79037 (14)0.0368 (4)
C290.1728 (2)0.32643 (16)0.83307 (14)0.0435 (4)
H290.17220.24930.83020.052*
C300.0485 (3)0.39089 (19)0.88076 (15)0.0517 (5)
H300.05440.36620.91530.062*
C310.0960 (3)0.49664 (19)0.86815 (16)0.0541 (5)
H310.03140.55800.89210.065*
C320.2502 (2)0.50038 (16)0.81311 (16)0.0451 (5)
H320.31200.56420.79330.054*
C330.0960 (3)0.3753 (2)0.60022 (16)0.0540 (5)
H330.14260.30630.58130.065*
C340.0535 (3)0.3921 (2)0.65521 (18)0.0628 (6)
H340.13080.33760.68100.075*
C350.0738 (3)0.4998 (3)0.6665 (2)0.0795 (9)
H350.16880.53510.70130.095*
C360.0650 (4)0.5504 (2)0.6174 (2)0.0794 (9)
H360.08340.62680.61180.095*
C370.1690 (3)0.4720 (2)0.57671 (16)0.0591 (6)
H370.27500.48310.53800.071*
N10.2691 (2)0.01468 (13)0.96630 (13)0.0475 (4)
N20.40502 (19)0.01406 (12)0.75560 (12)0.0413 (4)
N30.70264 (17)0.15638 (12)0.72110 (11)0.0372 (3)
O10.54339 (16)0.43293 (10)0.68911 (12)0.0518 (4)
F10.22731 (18)0.22959 (12)0.29030 (10)0.0684 (4)
Fe10.10914 (3)0.44031 (2)0.730212 (19)0.03701 (9)
S10.96553 (7)0.06529 (5)0.64716 (5)0.05986 (16)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0461 (11)0.0371 (10)0.0505 (12)0.0021 (8)0.0049 (9)0.0013 (8)
C20.0598 (14)0.0514 (12)0.0649 (15)0.0110 (11)0.0037 (12)0.0025 (11)
C30.0600 (14)0.0517 (13)0.088 (2)0.0202 (11)0.0078 (13)0.0027 (13)
C40.0757 (16)0.0484 (12)0.0747 (17)0.0171 (11)0.0247 (14)0.0036 (11)
C50.0651 (14)0.0446 (11)0.0559 (13)0.0098 (10)0.0135 (11)0.0058 (10)
C60.0463 (10)0.0338 (9)0.0462 (11)0.0021 (8)0.0103 (9)0.0014 (8)
C70.0385 (9)0.0335 (9)0.0338 (9)0.0008 (7)0.0060 (7)0.0007 (7)
C80.0428 (10)0.0370 (9)0.0353 (10)0.0016 (8)0.0051 (8)0.0006 (7)
C90.0431 (10)0.0436 (10)0.0335 (10)0.0019 (8)0.0069 (8)0.0036 (8)
C100.0623 (13)0.0670 (14)0.0336 (11)0.0057 (11)0.0012 (10)0.0078 (10)
C110.0735 (16)0.0840 (17)0.0392 (12)0.0091 (13)0.0060 (11)0.0247 (12)
C120.0607 (14)0.0718 (15)0.0517 (13)0.0141 (11)0.0117 (11)0.0233 (11)
C130.0452 (11)0.0581 (12)0.0421 (11)0.0096 (9)0.0082 (9)0.0121 (9)
C140.0364 (9)0.0425 (10)0.0343 (9)0.0014 (7)0.0073 (7)0.0064 (8)
C150.0368 (9)0.0353 (9)0.0316 (9)0.0027 (7)0.0046 (7)0.0047 (7)
C160.0341 (9)0.0316 (8)0.0320 (9)0.0037 (7)0.0065 (7)0.0047 (7)
C170.0384 (9)0.0322 (8)0.0328 (9)0.0046 (7)0.0040 (7)0.0037 (7)
C180.0396 (9)0.0357 (9)0.0344 (9)0.0013 (7)0.0034 (7)0.0062 (7)
C190.0440 (11)0.0502 (11)0.0438 (11)0.0028 (9)0.0001 (9)0.0103 (9)
C200.0477 (12)0.0574 (12)0.0443 (12)0.0095 (9)0.0073 (9)0.0013 (10)
C210.0388 (9)0.0349 (9)0.0319 (9)0.0011 (7)0.0021 (7)0.0078 (7)
C220.0546 (11)0.0359 (9)0.0390 (10)0.0070 (8)0.0077 (9)0.0031 (8)
C230.0526 (12)0.0425 (10)0.0488 (12)0.0091 (9)0.0085 (9)0.0135 (9)
C240.0493 (11)0.0538 (11)0.0356 (10)0.0021 (9)0.0114 (8)0.0148 (9)
C250.0542 (12)0.0428 (10)0.0346 (10)0.0006 (9)0.0071 (9)0.0018 (8)
C260.0447 (10)0.0358 (9)0.0366 (10)0.0048 (8)0.0031 (8)0.0048 (7)
C270.0351 (9)0.0339 (9)0.0383 (10)0.0012 (7)0.0113 (7)0.0057 (7)
C280.0397 (9)0.0393 (9)0.0336 (9)0.0001 (7)0.0112 (8)0.0069 (7)
C290.0433 (10)0.0483 (11)0.0363 (10)0.0001 (8)0.0041 (8)0.0006 (8)
C300.0438 (11)0.0721 (14)0.0349 (11)0.0040 (10)0.0002 (9)0.0019 (10)
C310.0577 (13)0.0649 (14)0.0405 (11)0.0150 (11)0.0076 (10)0.0210 (10)
C320.0491 (11)0.0451 (10)0.0460 (11)0.0046 (8)0.0153 (9)0.0186 (9)
C330.0558 (13)0.0695 (14)0.0418 (11)0.0021 (11)0.0155 (10)0.0170 (10)
C340.0495 (13)0.0940 (19)0.0493 (13)0.0165 (12)0.0147 (10)0.0095 (12)
C350.0613 (16)0.124 (3)0.0568 (16)0.0405 (17)0.0259 (13)0.0215 (16)
C360.133 (3)0.0550 (14)0.0589 (16)0.0013 (16)0.0489 (18)0.0058 (12)
C370.0595 (13)0.0843 (17)0.0350 (11)0.0204 (12)0.0102 (10)0.0015 (11)
N10.0524 (10)0.0433 (9)0.0419 (9)0.0045 (7)0.0020 (8)0.0001 (7)
N20.0482 (9)0.0367 (8)0.0386 (9)0.0056 (7)0.0058 (7)0.0030 (7)
N30.0353 (8)0.0419 (8)0.0336 (8)0.0018 (6)0.0052 (6)0.0039 (6)
O10.0434 (8)0.0372 (7)0.0726 (10)0.0090 (6)0.0001 (7)0.0102 (7)
F10.0779 (9)0.0831 (9)0.0541 (8)0.0073 (7)0.0334 (7)0.0122 (7)
Fe10.03496 (15)0.04285 (16)0.03363 (15)0.00073 (11)0.00654 (11)0.00640 (11)
S10.0445 (3)0.0693 (4)0.0606 (4)0.0151 (3)0.0026 (3)0.0046 (3)
Geometric parameters (Å, º) top
C1—N11.377 (3)C20—H20A0.9700
C1—C21.413 (3)C20—H20B0.9700
C1—C61.417 (3)C21—C261.382 (3)
C2—C31.362 (4)C21—C221.398 (3)
C2—H20.9300C22—C231.381 (3)
C3—C41.397 (4)C22—H220.9300
C3—H30.9300C23—C241.369 (3)
C4—C51.369 (3)C23—H230.9300
C4—H40.9300C24—F11.365 (2)
C5—C61.406 (3)C24—C251.365 (3)
C5—H50.9300C25—C261.386 (3)
C6—N21.380 (2)C25—H250.9300
C7—N21.301 (2)C26—H260.9300
C7—C81.423 (3)C27—O11.213 (2)
C7—C151.535 (2)C27—C281.461 (3)
C8—N11.312 (2)C28—C291.434 (3)
C8—C91.464 (3)C28—C321.434 (3)
C9—C101.383 (3)C28—Fe12.0191 (18)
C9—C141.397 (3)C29—C301.414 (3)
C10—C111.382 (3)C29—Fe12.025 (2)
C10—H100.9300C29—H290.9800
C11—C121.382 (3)C30—C311.405 (3)
C11—H110.9300C30—Fe12.045 (2)
C12—C131.385 (3)C30—H300.9800
C12—H120.9300C31—C321.407 (3)
C13—C141.385 (3)C31—Fe12.051 (2)
C13—H130.9300C31—H310.9800
C14—C151.520 (2)C32—Fe12.0398 (19)
C15—N31.464 (2)C32—H320.9800
C15—C161.588 (2)C33—C341.388 (3)
C16—C271.527 (2)C33—C371.389 (3)
C16—C171.551 (2)C33—Fe12.047 (2)
C16—H160.9800C33—H330.9800
C17—C211.513 (2)C34—C351.385 (4)
C17—C181.523 (3)C34—Fe12.047 (2)
C17—H170.9800C34—H340.9800
C18—N31.457 (2)C35—C361.415 (5)
C18—C191.520 (3)C35—Fe12.025 (2)
C18—H180.9800C35—H350.9800
C19—S11.821 (2)C36—C371.390 (4)
C19—H19A0.9700C36—Fe12.033 (2)
C19—H19B0.9700C36—H360.9800
C20—N31.444 (2)C37—Fe12.047 (2)
C20—S11.834 (2)C37—H370.9800
N1—C1—C2119.1 (2)C30—C29—C28107.56 (18)
N1—C1—C6122.18 (17)C30—C29—Fe170.45 (12)
C2—C1—C6118.7 (2)C28—C29—Fe169.03 (10)
C3—C2—C1120.3 (2)C30—C29—H29126.2
C3—C2—H2119.9C28—C29—H29126.2
C1—C2—H2119.9Fe1—C29—H29126.2
C2—C3—C4120.9 (2)C31—C30—C29108.56 (19)
C2—C3—H3119.6C31—C30—Fe170.15 (12)
C4—C3—H3119.6C29—C30—Fe168.88 (11)
C5—C4—C3120.5 (2)C31—C30—H30125.7
C5—C4—H4119.8C29—C30—H30125.7
C3—C4—H4119.8Fe1—C30—H30125.7
C4—C5—C6120.0 (2)C30—C31—C32108.85 (19)
C4—C5—H5120.0C30—C31—Fe169.72 (12)
C6—C5—H5120.0C32—C31—Fe169.46 (11)
N2—C6—C5118.71 (19)C30—C31—H31125.6
N2—C6—C1121.64 (18)C32—C31—H31125.6
C5—C6—C1119.62 (18)Fe1—C31—H31125.6
N2—C7—C8123.79 (17)C31—C32—C28107.73 (19)
N2—C7—C15125.82 (16)C31—C32—Fe170.31 (12)
C8—C7—C15110.17 (15)C28—C32—Fe168.53 (10)
N1—C8—C7123.68 (18)C31—C32—H32126.1
N1—C8—C9127.97 (18)C28—C32—H32126.1
C7—C8—C9108.30 (16)Fe1—C32—H32126.1
C10—C9—C14121.14 (19)C34—C33—C37109.0 (2)
C10—C9—C8130.35 (19)C34—C33—Fe170.18 (13)
C14—C9—C8108.51 (16)C37—C33—Fe170.17 (13)
C11—C10—C9118.2 (2)C34—C33—H33125.5
C11—C10—H10120.9C37—C33—H33125.5
C9—C10—H10120.9Fe1—C33—H33125.5
C12—C11—C10121.0 (2)C35—C34—C33107.6 (2)
C12—C11—H11119.5C35—C34—Fe169.27 (14)
C10—C11—H11119.5C33—C34—Fe170.16 (13)
C11—C12—C13121.0 (2)C35—C34—H34126.2
C11—C12—H12119.5C33—C34—H34126.2
C13—C12—H12119.5Fe1—C34—H34126.2
C12—C13—C14118.6 (2)C34—C35—C36108.3 (2)
C12—C13—H13120.7C34—C35—Fe170.97 (14)
C14—C13—H13120.7C36—C35—Fe169.87 (15)
C13—C14—C9120.10 (18)C34—C35—H35125.9
C13—C14—C15128.08 (17)C36—C35—H35125.9
C9—C14—C15111.79 (16)Fe1—C35—H35125.9
N3—C15—C14113.78 (14)C37—C36—C35107.2 (2)
N3—C15—C7117.55 (15)C37—C36—Fe170.63 (14)
C14—C15—C7100.86 (14)C35—C36—Fe169.30 (15)
N3—C15—C16100.78 (13)C37—C36—H36126.4
C14—C15—C16116.14 (14)C35—C36—H36126.4
C7—C15—C16108.37 (14)Fe1—C36—H36126.4
C27—C16—C17112.63 (14)C33—C37—C36107.9 (2)
C27—C16—C15112.86 (14)C33—C37—Fe170.15 (13)
C17—C16—C15105.89 (14)C36—C37—Fe169.52 (14)
C27—C16—H16108.4C33—C37—H37126.0
C17—C16—H16108.4C36—C37—H37126.0
C15—C16—H16108.4Fe1—C37—H37126.0
C21—C17—C18116.13 (15)C8—N1—C1114.09 (17)
C21—C17—C16112.03 (14)C7—N2—C6114.56 (16)
C18—C17—C16103.55 (14)C20—N3—C18108.64 (15)
C21—C17—H17108.3C20—N3—C15120.93 (15)
C18—C17—H17108.3C18—N3—C15108.06 (14)
C16—C17—H17108.3C28—Fe1—C2941.54 (7)
N3—C18—C19104.67 (15)C28—Fe1—C35174.75 (12)
N3—C18—C17101.91 (14)C29—Fe1—C35143.28 (12)
C19—C18—C17119.10 (16)C28—Fe1—C36134.60 (12)
N3—C18—H18110.2C29—Fe1—C36174.29 (12)
C19—C18—H18110.2C35—Fe1—C3640.83 (13)
C17—C18—H18110.2C28—Fe1—C3241.38 (7)
C18—C19—S1104.45 (14)C29—Fe1—C3269.28 (8)
C18—C19—H19A110.9C35—Fe1—C32134.48 (12)
S1—C19—H19A110.9C36—Fe1—C32110.44 (11)
C18—C19—H19B110.9C28—Fe1—C3068.86 (8)
S1—C19—H19B110.9C29—Fe1—C3040.67 (8)
H19A—C19—H19B108.9C35—Fe1—C30113.71 (11)
N3—C20—S1103.11 (13)C36—Fe1—C30144.91 (12)
N3—C20—H20A111.1C32—Fe1—C3068.10 (9)
S1—C20—H20A111.1C28—Fe1—C33115.19 (8)
N3—C20—H20B111.1C29—Fe1—C33110.01 (9)
S1—C20—H20B111.1C35—Fe1—C3366.68 (11)
H20A—C20—H20B109.1C36—Fe1—C3366.88 (11)
C26—C21—C22118.07 (17)C32—Fe1—C33146.57 (9)
C26—C21—C17120.58 (16)C30—Fe1—C33134.19 (10)
C22—C21—C17121.22 (16)C28—Fe1—C37110.62 (9)
C23—C22—C21121.04 (18)C29—Fe1—C37134.77 (10)
C23—C22—H22119.5C35—Fe1—C3767.38 (11)
C21—C22—H22119.5C36—Fe1—C3739.85 (12)
C24—C23—C22118.27 (18)C32—Fe1—C37116.09 (9)
C24—C23—H23120.9C30—Fe1—C37173.50 (10)
C22—C23—H23120.9C33—Fe1—C3739.68 (9)
F1—C24—C25118.57 (19)C28—Fe1—C34144.67 (10)
F1—C24—C23118.40 (19)C29—Fe1—C34113.39 (10)
C25—C24—C23123.02 (19)C35—Fe1—C3439.76 (12)
C24—C25—C26117.92 (18)C36—Fe1—C3467.59 (12)
C24—C25—H25121.0C32—Fe1—C34173.03 (10)
C26—C25—H25121.0C30—Fe1—C34109.37 (10)
C21—C26—C25121.67 (17)C33—Fe1—C3439.65 (9)
C21—C26—H26119.2C37—Fe1—C3467.06 (9)
C25—C26—H26119.2C28—Fe1—C3168.63 (8)
O1—C27—C28121.81 (16)C29—Fe1—C3168.35 (9)
O1—C27—C16121.04 (16)C35—Fe1—C31110.11 (10)
C28—C27—C16117.15 (15)C36—Fe1—C31115.37 (11)
C29—C28—C32107.30 (17)C32—Fe1—C3140.23 (9)
C29—C28—C27127.91 (16)C30—Fe1—C3140.13 (9)
C32—C28—C27124.22 (17)C33—Fe1—C31172.76 (9)
C29—C28—Fe169.43 (11)C37—Fe1—C31146.21 (10)
C32—C28—Fe170.08 (11)C34—Fe1—C31133.81 (10)
C27—C28—Fe1119.05 (13)C19—S1—C2093.34 (9)
N1—C1—C2—C3178.2 (2)C29—C28—Fe1—C3037.83 (12)
C6—C1—C2—C30.5 (3)C32—C28—Fe1—C3080.45 (13)
C1—C2—C3—C41.8 (4)C27—C28—Fe1—C30160.67 (16)
C2—C3—C4—C51.7 (4)C29—C28—Fe1—C3392.26 (13)
C3—C4—C5—C60.6 (4)C32—C28—Fe1—C33149.46 (13)
C4—C5—C6—N2175.1 (2)C27—C28—Fe1—C3330.58 (17)
C4—C5—C6—C12.8 (3)C29—C28—Fe1—C37135.23 (13)
N1—C1—C6—N22.4 (3)C32—C28—Fe1—C37106.49 (14)
C2—C1—C6—N2175.1 (2)C27—C28—Fe1—C3712.39 (17)
N1—C1—C6—C5179.65 (19)C29—C28—Fe1—C3456.14 (19)
C2—C1—C6—C52.8 (3)C32—C28—Fe1—C34174.42 (15)
N2—C7—C8—N12.1 (3)C27—C28—Fe1—C3466.7 (2)
C15—C7—C8—N1172.84 (18)C29—C28—Fe1—C3181.04 (13)
N2—C7—C8—C9179.87 (17)C27—C28—Fe1—C31156.12 (17)
C15—C7—C8—C94.9 (2)C30—C29—Fe1—C28118.62 (17)
N1—C8—C9—C103.1 (4)C30—C29—Fe1—C3558.1 (2)
C7—C8—C9—C10179.2 (2)C28—C29—Fe1—C35176.72 (16)
N1—C8—C9—C14176.19 (19)C30—C29—Fe1—C3280.12 (14)
C7—C8—C9—C141.5 (2)C28—C29—Fe1—C3238.50 (11)
C14—C9—C10—C110.5 (3)C28—C29—Fe1—C30118.62 (17)
C8—C9—C10—C11179.7 (2)C30—C29—Fe1—C33135.60 (14)
C9—C10—C11—C120.3 (4)C28—C29—Fe1—C33105.78 (12)
C10—C11—C12—C130.2 (4)C30—C29—Fe1—C37173.20 (13)
C11—C12—C13—C140.8 (4)C28—C29—Fe1—C3768.19 (16)
C12—C13—C14—C91.5 (3)C30—C29—Fe1—C3492.93 (15)
C12—C13—C14—C15176.3 (2)C28—C29—Fe1—C34148.45 (12)
C10—C9—C14—C131.4 (3)C30—C29—Fe1—C3136.85 (13)
C8—C9—C14—C13179.18 (18)C28—C29—Fe1—C3181.77 (13)
C10—C9—C14—C15176.75 (19)C34—C35—Fe1—C2955.0 (2)
C8—C9—C14—C152.6 (2)C36—C35—Fe1—C29173.67 (16)
C13—C14—C15—N350.0 (3)C34—C35—Fe1—C36118.6 (2)
C9—C14—C15—N3132.05 (16)C34—C35—Fe1—C32174.18 (14)
C13—C14—C15—C7176.76 (19)C36—C35—Fe1—C3267.2 (2)
C9—C14—C15—C75.2 (2)C34—C35—Fe1—C3092.21 (17)
C13—C14—C15—C1666.4 (3)C36—C35—Fe1—C30149.15 (16)
C9—C14—C15—C16111.59 (18)C34—C35—Fe1—C3337.56 (15)
N2—C7—C15—N354.8 (2)C36—C35—Fe1—C3381.07 (18)
C8—C7—C15—N3130.35 (17)C34—C35—Fe1—C3780.82 (16)
N2—C7—C15—C14179.12 (18)C36—C35—Fe1—C3737.81 (16)
C8—C7—C15—C146.08 (19)C36—C35—Fe1—C34118.6 (2)
N2—C7—C15—C1658.4 (2)C34—C35—Fe1—C31135.45 (16)
C8—C7—C15—C16116.36 (16)C36—C35—Fe1—C31105.91 (18)
N3—C15—C16—C27109.51 (15)C37—C36—Fe1—C2865.81 (19)
C14—C15—C16—C2713.9 (2)C35—C36—Fe1—C28176.23 (15)
C7—C15—C16—C27126.49 (15)C37—C36—Fe1—C35118.0 (2)
N3—C15—C16—C1714.15 (16)C37—C36—Fe1—C32106.61 (15)
C14—C15—C16—C17137.56 (15)C35—C36—Fe1—C32135.43 (17)
C7—C15—C16—C17109.85 (15)C37—C36—Fe1—C30172.70 (15)
C27—C16—C17—C2198.14 (17)C35—C36—Fe1—C3054.7 (3)
C15—C16—C17—C21138.06 (14)C37—C36—Fe1—C3337.41 (14)
C27—C16—C17—C18135.97 (15)C35—C36—Fe1—C3380.55 (18)
C15—C16—C17—C1812.17 (16)C35—C36—Fe1—C37118.0 (2)
C21—C17—C18—N3157.44 (14)C37—C36—Fe1—C3480.57 (16)
C16—C17—C18—N334.21 (16)C35—C36—Fe1—C3437.39 (16)
C21—C17—C18—C1988.1 (2)C37—C36—Fe1—C31150.14 (14)
C16—C17—C18—C19148.65 (16)C35—C36—Fe1—C3191.90 (18)
N3—C18—C19—S137.60 (16)C31—C32—Fe1—C28119.23 (18)
C17—C18—C19—S1150.55 (14)C31—C32—Fe1—C2980.59 (14)
C18—C17—C21—C26128.77 (18)C28—C32—Fe1—C2938.64 (11)
C16—C17—C21—C26112.55 (18)C31—C32—Fe1—C3565.5 (2)
C18—C17—C21—C2255.4 (2)C28—C32—Fe1—C35175.29 (15)
C16—C17—C21—C2263.2 (2)C31—C32—Fe1—C36105.50 (17)
C26—C21—C22—C230.6 (3)C28—C32—Fe1—C36135.27 (15)
C17—C21—C22—C23175.32 (18)C31—C32—Fe1—C3036.80 (13)
C21—C22—C23—C240.3 (3)C28—C32—Fe1—C3082.42 (13)
C22—C23—C24—F1179.06 (18)C31—C32—Fe1—C33175.80 (16)
C22—C23—C24—C250.1 (3)C28—C32—Fe1—C3356.6 (2)
F1—C24—C25—C26179.02 (17)C31—C32—Fe1—C37148.64 (15)
C23—C24—C25—C260.2 (3)C28—C32—Fe1—C3792.14 (14)
C22—C21—C26—C250.5 (3)C28—C32—Fe1—C31119.23 (18)
C17—C21—C26—C25175.38 (17)C31—C30—Fe1—C2881.52 (14)
C24—C25—C26—C210.2 (3)C29—C30—Fe1—C2838.62 (12)
C17—C16—C27—O125.5 (2)C31—C30—Fe1—C29120.15 (19)
C15—C16—C27—O194.4 (2)C31—C30—Fe1—C3593.52 (17)
C17—C16—C27—C28154.34 (15)C29—C30—Fe1—C35146.33 (16)
C15—C16—C27—C2885.81 (19)C31—C30—Fe1—C3657.9 (2)
O1—C27—C28—C29177.49 (19)C29—C30—Fe1—C36178.00 (18)
C16—C27—C28—C292.3 (3)C31—C30—Fe1—C3236.89 (13)
O1—C27—C28—C327.3 (3)C29—C30—Fe1—C3283.26 (13)
C16—C27—C28—C32172.54 (17)C31—C30—Fe1—C33173.38 (13)
O1—C27—C28—Fe191.9 (2)C29—C30—Fe1—C3366.47 (17)
C16—C27—C28—Fe187.91 (17)C31—C30—Fe1—C34136.17 (14)
C32—C28—C29—C300.1 (2)C29—C30—Fe1—C34103.68 (15)
C27—C28—C29—C30171.60 (18)C29—C30—Fe1—C31120.15 (19)
Fe1—C28—C29—C3060.19 (14)C34—C33—Fe1—C28147.72 (15)
C32—C28—C29—Fe160.13 (13)C37—C33—Fe1—C2892.45 (16)
C27—C28—C29—Fe1111.41 (19)C34—C33—Fe1—C29102.87 (16)
C28—C29—C30—C310.2 (2)C37—C33—Fe1—C29137.29 (15)
Fe1—C29—C30—C3159.09 (15)C34—C33—Fe1—C3537.66 (18)
C28—C29—C30—Fe159.29 (13)C37—C33—Fe1—C3582.17 (19)
C29—C30—C31—C320.3 (2)C34—C33—Fe1—C3682.27 (19)
Fe1—C30—C31—C3258.57 (15)C37—C33—Fe1—C3637.56 (17)
C29—C30—C31—Fe158.31 (15)C34—C33—Fe1—C32174.71 (17)
C30—C31—C32—C280.2 (2)C37—C33—Fe1—C3254.9 (2)
Fe1—C31—C32—C2858.50 (13)C34—C33—Fe1—C3063.4 (2)
C30—C31—C32—Fe158.73 (15)C37—C33—Fe1—C30176.78 (14)
C29—C28—C32—C310.1 (2)C34—C33—Fe1—C37119.8 (2)
C27—C28—C32—C31171.83 (17)C37—C33—Fe1—C34119.8 (2)
Fe1—C28—C32—C3159.62 (14)C33—C37—Fe1—C28104.99 (14)
C29—C28—C32—Fe159.72 (13)C36—C37—Fe1—C28136.05 (17)
C27—C28—C32—Fe1112.22 (18)C33—C37—Fe1—C2963.85 (18)
C37—C33—C34—C350.3 (3)C36—C37—Fe1—C29177.19 (16)
Fe1—C33—C34—C3559.40 (17)C33—C37—Fe1—C3580.23 (18)
C37—C33—C34—Fe159.65 (16)C36—C37—Fe1—C3538.72 (18)
C33—C34—C35—C360.2 (3)C33—C37—Fe1—C36119.0 (2)
Fe1—C34—C35—C3660.20 (18)C33—C37—Fe1—C32149.89 (14)
C33—C34—C35—Fe159.96 (16)C36—C37—Fe1—C3291.16 (18)
C34—C35—C36—C370.1 (3)C36—C37—Fe1—C33119.0 (2)
Fe1—C35—C36—C3760.75 (17)C33—C37—Fe1—C3436.95 (15)
C34—C35—C36—Fe160.88 (18)C36—C37—Fe1—C3482.01 (19)
C34—C33—C37—C360.2 (3)C33—C37—Fe1—C31172.93 (16)
Fe1—C33—C37—C3659.49 (16)C36—C37—Fe1—C3154.0 (2)
C34—C33—C37—Fe159.66 (16)C35—C34—Fe1—C28175.39 (16)
C35—C36—C37—C330.0 (3)C33—C34—Fe1—C2856.7 (2)
Fe1—C36—C37—C3359.88 (16)C35—C34—Fe1—C29147.74 (16)
C35—C36—C37—Fe159.90 (17)C33—C34—Fe1—C2993.57 (16)
C7—C8—N1—C10.7 (3)C33—C34—Fe1—C35118.7 (2)
C9—C8—N1—C1178.01 (18)C35—C34—Fe1—C3638.37 (18)
C2—C1—N1—C8176.14 (19)C33—C34—Fe1—C3680.32 (18)
C6—C1—N1—C81.4 (3)C35—C34—Fe1—C30104.12 (18)
C8—C7—N2—C61.1 (3)C33—C34—Fe1—C30137.19 (15)
C15—C7—N2—C6173.07 (17)C35—C34—Fe1—C33118.7 (2)
C5—C6—N2—C7178.99 (18)C35—C34—Fe1—C3781.71 (18)
C1—C6—N2—C71.1 (3)C33—C34—Fe1—C3736.98 (16)
S1—C20—N3—C1844.82 (17)C35—C34—Fe1—C3165.9 (2)
S1—C20—N3—C15170.52 (13)C33—C34—Fe1—C31175.40 (14)
C19—C18—N3—C2055.58 (19)C30—C31—Fe1—C2882.14 (13)
C17—C18—N3—C20179.74 (15)C32—C31—Fe1—C2838.28 (12)
C19—C18—N3—C15171.53 (14)C30—C31—Fe1—C2937.32 (13)
C17—C18—N3—C1546.85 (17)C32—C31—Fe1—C2983.10 (13)
C14—C15—N3—C2071.3 (2)C30—C31—Fe1—C35103.31 (17)
C7—C15—N3—C2046.3 (2)C32—C31—Fe1—C35136.27 (16)
C16—C15—N3—C20163.71 (16)C30—C31—Fe1—C36147.40 (16)
C14—C15—N3—C18162.77 (14)C32—C31—Fe1—C3692.18 (17)
C7—C15—N3—C1879.71 (18)C30—C31—Fe1—C32120.42 (19)
C16—C15—N3—C1837.75 (16)C32—C31—Fe1—C30120.42 (19)
C32—C28—Fe1—C29118.28 (16)C30—C31—Fe1—C37177.60 (16)
C27—C28—Fe1—C29122.84 (18)C32—C31—Fe1—C3757.2 (2)
C29—C28—Fe1—C36173.88 (14)C30—C31—Fe1—C3464.86 (19)
C32—C28—Fe1—C3667.84 (18)C32—C31—Fe1—C34174.72 (14)
C27—C28—Fe1—C3651.0 (2)C18—C19—S1—C2011.28 (15)
C29—C28—Fe1—C32118.28 (16)N3—C20—S1—C1917.86 (15)
C27—C28—Fe1—C32118.88 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C25—H25···O1i0.932.543.212 (2)129
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C25—H25···O1i0.932.543.212 (2)129
Symmetry code: (i) x+1, y+1, z+1.
 

Acknowledgements

The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection. SS and DV thank the UGC (SAP–CAS) for the departmental facilities. SS also thanks UGC for a meritorious Fellowship.

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