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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 9| September 2013| Pages m512-m513

2-(4-Bromo­benzo­yl)-1-ferrocenyl­spiro­[11H-pyrrolidizine-3,11′-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 8 August 2013; accepted 16 August 2013; online 23 August 2013)

In the title compound, [Fe(C5H5)(C33H25BrN3O)], the fused four-ring system, 11H-indeno­[1,2-b]quinoxaline is essentially planar, with a maximum deviation of 0.087 (3) Å from the least-squares plane of the attached benzene ring. The pyrrolidine rings adopt envelope conformation and make a dihedral angle of 51.76 (19)° with each other. The cyclopentadiene rings of the ferrocenyl moiety have an eclipsed conformation. The Br atom deviates by 0.0190 (9) Å from the attached benzene ring. The mol­ecular structure features an intra­molecular C—H⋯N inter­action, which generates an S(8) ring motif. The crystal packing features C—H⋯O inter­actions, which generate R22(18) centrosymmetric dimers, as well as 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 a related structure, see: Vijayakumar et al. (2012[Vijayakumar, B., Gavaskar, D., Srinivasan, T., Raghunathan, R. & Velmurugan, D. (2012). Acta Cryst. E68, m1382-m1383.]). For graph-set notation, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • [Fe(C5H5)(C33H25BrN3O)]

  • Mr = 680.41

  • Triclinic, [P \overline 1]

  • a = 9.3668 (3) Å

  • b = 9.9785 (3) Å

  • c = 18.6303 (5) Å

  • α = 89.724 (1)°

  • β = 75.967 (1)°

  • γ = 63.236 (1)°

  • V = 1497.37 (8) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 1.88 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 = 0.603, Tmax = 0.706

  • 22634 measured reflections

  • 6177 independent reflections

  • 5078 reflections with I > 2σ(I)

  • Rint = 0.028

Refinement
  • R[F2 > 2σ(F2)] = 0.053

  • wR(F2) = 0.137

  • S = 1.04

  • 6177 reflections

  • 397 parameters

  • H-atom parameters constrained

  • Δρmax = 1.87 e Å−3

  • Δρmin = −1.63 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C29–C33, C9–C15 and N1/N2/C1/C6/C7/C11 rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
C28—H28⋯N2 0.93 2.56 3.358 (5) 145
C13—H13⋯O1i 0.93 2.58 3.318 (4) 137
C4—H4⋯Cg1ii 0.93 2.69 3.580 (4) 159
C17—H17BCg2iii 0.97 2.84 3.743 (4) 155
C36—H36⋯Cg3iv 0.98 2.70 3.486 (5) 137
Symmetry codes: (i) -x+1, -y, -z+2; (ii) -x+1, -y+1, -z+1; (iii) -x+1, -y+1, -z+2; (iv) x-1, y, z.

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

Biological activities like antimalarial, antifungal (Biot et al., 2004), antitumor (Jaouen et al., 2004), and antibacterial (Fouda et al., 2007) are well known for ferrocene containing compounds. The information of molecular conformation and crystal packing of the title compound were obtained and analyzed using X-ray diffraction study against this background.

In the title compound, the four fused ring system, 11H-indeno[1,2-b]quinoxaline is essentially planar with a maximum deviation of -0.087 (3) Å for C8 atom. The pyrrolidine ring (N3/C16–C19) adopts a C17-envelope conformation with C17 -0.230 (4) Å out of the mean plane formed by the remaining ring atoms. The pyrrolidine ring (N3/C8/C19–C21) adopts a C21-envelope conformation with C21 -0.211 (3) Å out of the mean plane formed by the remaining ring atoms; the pyrrolidine rings make a dihedral angle of 51.76 (19)° with each other. The pyrrolidine ring (N3/C8/C19/C20/C21) makes a dihedral angle of 87.40 (18)° with the cyclopentane ring (C7-C11) which shows they are almost orthogonal to each other. The dihedral angle between the cp rings in the ferrocene moiety is 4.8 (2) °, which shows that they are almost coplanar to each other. The bromine atom Br1 attached with the benzenel ring (C23-C28) deviates by 0.0190 (9)Å.

The molecular structure is stabilized by C28—H28···N2 intramolecular interaction, which generates a S(8) ring motif (Fig. 1). The crystal packing is stabilized by inter-molecular C13—H13···O1i interactions, which generate R22(18) centrosymmetric dimers (Bernstein et al., 1995) (Fig. 2). The crystal packing is further stabilized by inter-molecular C4—H4···Cg1, C17—H17B···Cg2 and C36—H36···Cg3 inter-molecular interactions, where Cg1, Cg2 and Cg3 are the centers of gravity of rings (C29–C33), (C9–C15) and (N1/N2/C1/C6/C7/C11), respectively (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 a related structure, see: Vijayakumar et al. (2012). For graph-set notation, see: Bernstein et al. (1995).

Experimental top

Ninhydrin (1 mM) and 1, 2-phenylenediamine (1 mM) were mixed and stirred with 10 mL of methanol for 10 min. To this mixture proline (1 mM) and 1-ferrcenyl- 3-(4-bromo)benzoyl-prop-2-ene dipolarophile (1 mM) 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 petroleum ether and ethyl acetate (4:1). 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 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 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 compound, showing displacement ellipsoids drawn at the 30% probability level.
[Figure 2] Fig. 2. The crystal packing of the title compound viewed down the b axis. H-atoms not involved in H-bonds have been excluded for clarity.
2-(4-Bromobenzoyl)-1-ferrocenylspiro[11H-pyrrolidizine-3,11'-indeno[1,2-b]quinoxaline] top
Crystal data top
[Fe(C5H5)(C33H25BrN3O)]Z = 2
Mr = 680.41F(000) = 696
Triclinic, P1Dx = 1.509 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.3668 (3) ÅCell parameters from 6177 reflections
b = 9.9785 (3) Åθ = 1.1–26.5°
c = 18.6303 (5) ŵ = 1.88 mm1
α = 89.724 (1)°T = 293 K
β = 75.967 (1)°Block, colourless
γ = 63.236 (1)°0.30 × 0.25 × 0.20 mm
V = 1497.37 (8) Å3
Data collection top
Bruker SMART APEXII area-detector
diffractometer
6177 independent reflections
Radiation source: fine-focus sealed tube5078 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
ω and ϕ scansθmax = 26.5°, θmin = 1.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
h = 1011
Tmin = 0.603, Tmax = 0.706k = 1212
22634 measured reflectionsl = 2322
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)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0539P)2 + 2.514P]
where P = (Fo2 + 2Fc2)/3
6177 reflections(Δ/σ)max = 0.001
397 parametersΔρmax = 1.87 e Å3
0 restraintsΔρmin = 1.63 e Å3
Crystal data top
[Fe(C5H5)(C33H25BrN3O)]γ = 63.236 (1)°
Mr = 680.41V = 1497.37 (8) Å3
Triclinic, P1Z = 2
a = 9.3668 (3) ÅMo Kα radiation
b = 9.9785 (3) ŵ = 1.88 mm1
c = 18.6303 (5) ÅT = 293 K
α = 89.724 (1)°0.30 × 0.25 × 0.20 mm
β = 75.967 (1)°
Data collection top
Bruker SMART APEXII area-detector
diffractometer
6177 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
5078 reflections with I > 2σ(I)
Tmin = 0.603, Tmax = 0.706Rint = 0.028
22634 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0530 restraints
wR(F2) = 0.137H-atom parameters constrained
S = 1.04Δρmax = 1.87 e Å3
6177 reflectionsΔρmin = 1.63 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
C10.8769 (4)0.1667 (4)0.66122 (18)0.0415 (7)
C21.0270 (5)0.1122 (5)0.6044 (2)0.0648 (11)
H21.12660.04610.61410.078*
C31.0257 (6)0.1565 (6)0.5353 (3)0.0797 (14)
H31.12500.12020.49800.096*
C40.8782 (6)0.2554 (6)0.5196 (2)0.0740 (13)
H40.87990.28390.47190.089*
C50.7313 (5)0.3108 (5)0.5734 (2)0.0557 (10)
H50.63320.37620.56220.067*
C60.7274 (4)0.2693 (4)0.64563 (17)0.0386 (7)
C70.5854 (4)0.2820 (3)0.76391 (15)0.0304 (6)
C80.4385 (3)0.3328 (3)0.83310 (15)0.0295 (6)
C90.5232 (4)0.2280 (3)0.88732 (16)0.0320 (6)
C100.6945 (4)0.1452 (3)0.85599 (16)0.0343 (6)
C110.7351 (4)0.1757 (3)0.77898 (16)0.0328 (6)
C120.7994 (4)0.0525 (4)0.89628 (18)0.0431 (8)
H120.91310.00190.87460.052*
C130.7309 (5)0.0429 (4)0.96949 (19)0.0455 (8)
H130.79890.01730.99800.055*
C140.5617 (4)0.1226 (4)1.00030 (17)0.0407 (7)
H140.51730.11411.04940.049*
C150.4560 (4)0.2150 (4)0.96023 (17)0.0374 (7)
H150.34210.26720.98190.045*
C160.4140 (4)0.5472 (4)0.91829 (19)0.0408 (7)
H16A0.44450.62680.90530.049*
H16B0.50580.46400.93110.049*
C170.2585 (4)0.6056 (4)0.98274 (18)0.0450 (8)
H17A0.25030.52381.00870.054*
H17B0.25520.67901.01790.054*
C180.1230 (4)0.6781 (4)0.94348 (18)0.0430 (7)
H18A0.10280.78040.93530.052*
H18B0.02040.68060.97240.052*
C190.1898 (4)0.5771 (3)0.86938 (16)0.0326 (6)
H190.16200.64050.82950.039*
C200.1343 (3)0.4550 (3)0.86635 (16)0.0317 (6)
H200.11340.42420.91620.038*
C210.2879 (3)0.3238 (3)0.81511 (15)0.0302 (6)
H210.28990.34560.76360.036*
C220.2901 (4)0.1712 (4)0.82134 (18)0.0391 (7)
C230.3566 (4)0.0614 (4)0.7524 (2)0.0424 (7)
C240.3524 (5)0.0764 (4)0.7587 (3)0.0576 (10)
H240.31030.09890.80510.069*
C250.4111 (6)0.1799 (5)0.6958 (3)0.0734 (14)
H250.40950.27220.70020.088*
C260.4712 (5)0.1460 (5)0.6274 (3)0.0655 (12)
C270.4777 (5)0.0127 (5)0.6198 (2)0.0601 (10)
H270.52010.00850.57310.072*
C280.4208 (4)0.0906 (4)0.6822 (2)0.0484 (8)
H280.42550.18140.67700.058*
C290.0989 (6)0.4878 (5)0.6368 (2)0.0650 (11)
H290.16030.37930.61940.078*
C300.0631 (6)0.5873 (7)0.6318 (2)0.0728 (14)
H300.13340.56050.61000.087*
C310.1036 (5)0.7318 (6)0.6630 (2)0.0672 (13)
H310.20810.82370.66720.081*
C320.0316 (5)0.7225 (5)0.6868 (2)0.0536 (9)
H320.03730.80640.71080.064*
C330.1567 (4)0.5718 (5)0.6704 (2)0.0511 (9)
H330.26480.53210.68120.061*
C340.1484 (4)0.6599 (4)0.85115 (17)0.0405 (7)
H340.14910.74730.87540.049*
C350.2744 (4)0.6630 (5)0.82032 (19)0.0484 (8)
H350.37760.75290.82010.058*
C360.2267 (4)0.5159 (5)0.7909 (2)0.0518 (9)
H360.29040.48510.76620.062*
C370.0698 (4)0.4184 (4)0.80284 (19)0.0435 (8)
H370.00610.30930.78730.052*
C380.0201 (4)0.5077 (4)0.84020 (16)0.0348 (6)
N10.8802 (3)0.1180 (3)0.73019 (15)0.0420 (6)
N20.5773 (3)0.3290 (3)0.69911 (14)0.0356 (6)
N30.3720 (3)0.4961 (3)0.85602 (13)0.0321 (5)
O10.2360 (4)0.1392 (3)0.88107 (15)0.0613 (7)
Fe10.05693 (5)0.58417 (5)0.74004 (2)0.03596 (14)
Br10.54872 (10)0.28490 (7)0.54137 (4)0.1181 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0385 (17)0.0447 (18)0.0328 (16)0.0166 (14)0.0003 (13)0.0003 (13)
C20.041 (2)0.077 (3)0.052 (2)0.014 (2)0.0034 (17)0.004 (2)
C30.059 (3)0.103 (4)0.049 (2)0.028 (3)0.015 (2)0.006 (2)
C40.077 (3)0.099 (4)0.037 (2)0.040 (3)0.001 (2)0.017 (2)
C50.056 (2)0.073 (3)0.0352 (18)0.029 (2)0.0085 (16)0.0162 (17)
C60.0418 (17)0.0453 (18)0.0287 (15)0.0228 (15)0.0043 (13)0.0044 (13)
C70.0322 (14)0.0306 (14)0.0272 (14)0.0135 (12)0.0080 (11)0.0044 (11)
C80.0308 (14)0.0293 (14)0.0249 (13)0.0113 (12)0.0067 (11)0.0045 (11)
C90.0375 (15)0.0304 (14)0.0270 (14)0.0139 (12)0.0104 (12)0.0049 (11)
C100.0399 (16)0.0298 (15)0.0304 (15)0.0128 (13)0.0114 (12)0.0050 (12)
C110.0326 (15)0.0297 (14)0.0319 (15)0.0106 (12)0.0094 (12)0.0022 (11)
C120.0425 (18)0.0355 (16)0.0420 (18)0.0073 (14)0.0169 (14)0.0071 (14)
C130.059 (2)0.0363 (17)0.0393 (18)0.0154 (16)0.0246 (16)0.0129 (14)
C140.062 (2)0.0381 (17)0.0266 (15)0.0257 (16)0.0135 (14)0.0096 (12)
C150.0429 (17)0.0361 (16)0.0315 (15)0.0179 (14)0.0079 (13)0.0061 (12)
C160.0357 (16)0.0385 (17)0.0493 (19)0.0153 (14)0.0170 (14)0.0033 (14)
C170.054 (2)0.0453 (19)0.0358 (17)0.0209 (16)0.0158 (15)0.0010 (14)
C180.0345 (16)0.0441 (18)0.0411 (18)0.0117 (14)0.0070 (13)0.0095 (14)
C190.0312 (14)0.0317 (15)0.0320 (15)0.0105 (12)0.0119 (12)0.0032 (12)
C200.0309 (14)0.0382 (15)0.0250 (14)0.0153 (13)0.0069 (11)0.0055 (11)
C210.0333 (14)0.0333 (15)0.0249 (13)0.0154 (12)0.0094 (11)0.0052 (11)
C220.0422 (17)0.0375 (16)0.0422 (18)0.0194 (14)0.0175 (14)0.0110 (14)
C230.0390 (17)0.0322 (16)0.059 (2)0.0137 (14)0.0234 (15)0.0039 (14)
C240.060 (2)0.0398 (19)0.082 (3)0.0240 (18)0.033 (2)0.0107 (19)
C250.075 (3)0.035 (2)0.119 (4)0.022 (2)0.049 (3)0.002 (2)
C260.058 (2)0.045 (2)0.084 (3)0.0070 (19)0.035 (2)0.018 (2)
C270.057 (2)0.053 (2)0.062 (2)0.0159 (19)0.0194 (19)0.0120 (18)
C280.050 (2)0.0398 (18)0.053 (2)0.0180 (16)0.0156 (16)0.0040 (15)
C290.071 (3)0.074 (3)0.0335 (19)0.028 (2)0.0031 (18)0.0028 (18)
C300.074 (3)0.123 (4)0.036 (2)0.053 (3)0.025 (2)0.017 (2)
C310.048 (2)0.087 (3)0.052 (2)0.017 (2)0.0178 (18)0.035 (2)
C320.055 (2)0.059 (2)0.048 (2)0.0292 (19)0.0099 (17)0.0200 (17)
C330.0373 (17)0.070 (2)0.0415 (19)0.0228 (18)0.0069 (14)0.0207 (17)
C340.0303 (15)0.0507 (19)0.0332 (16)0.0146 (14)0.0045 (12)0.0004 (14)
C350.0277 (15)0.068 (2)0.0429 (18)0.0174 (16)0.0082 (13)0.0077 (17)
C360.0408 (18)0.076 (3)0.054 (2)0.0379 (19)0.0158 (16)0.0109 (19)
C370.0438 (18)0.051 (2)0.0462 (19)0.0301 (16)0.0140 (15)0.0101 (15)
C380.0308 (14)0.0470 (18)0.0276 (14)0.0203 (13)0.0054 (11)0.0063 (12)
N10.0332 (13)0.0411 (15)0.0395 (15)0.0088 (12)0.0056 (11)0.0018 (12)
N20.0357 (13)0.0417 (14)0.0285 (13)0.0173 (11)0.0084 (10)0.0072 (11)
N30.0302 (12)0.0313 (12)0.0325 (13)0.0122 (10)0.0085 (10)0.0023 (10)
O10.094 (2)0.0613 (17)0.0467 (15)0.0507 (16)0.0196 (14)0.0214 (13)
Fe10.0312 (2)0.0472 (3)0.0305 (2)0.0182 (2)0.00988 (17)0.00543 (18)
Br10.1451 (6)0.0685 (4)0.1205 (5)0.0226 (4)0.0544 (5)0.0415 (3)
Geometric parameters (Å, º) top
C1—N11.374 (4)C20—H200.9800
C1—C21.410 (5)C21—C221.518 (4)
C1—C61.414 (5)C21—H210.9800
C2—C31.360 (6)C22—O11.211 (4)
C2—H20.9300C22—C231.499 (5)
C3—C41.391 (7)C23—C281.390 (5)
C3—H30.9300C23—C241.397 (5)
C4—C51.362 (6)C24—C251.390 (6)
C4—H40.9300C24—H240.9300
C5—C61.403 (5)C25—C261.369 (7)
C5—H50.9300C25—H250.9300
C6—N21.377 (4)C26—C271.364 (6)
C7—N21.300 (4)C26—Br11.889 (4)
C7—C111.421 (4)C27—C281.383 (5)
C7—C81.526 (4)C27—H270.9300
C8—N31.480 (4)C28—H280.9300
C8—C91.541 (4)C29—C331.403 (6)
C8—C211.566 (4)C29—C301.417 (7)
C9—C151.384 (4)C29—Fe12.037 (4)
C9—C101.398 (4)C29—H290.9800
C10—C121.385 (4)C30—C311.403 (7)
C10—C111.460 (4)C30—Fe12.031 (4)
C11—N11.306 (4)C30—H300.9800
C12—C131.383 (5)C31—C321.406 (6)
C12—H120.9300C31—Fe12.031 (4)
C13—C141.379 (5)C31—H310.9800
C13—H130.9300C32—C331.404 (6)
C14—C151.385 (4)C32—Fe12.048 (4)
C14—H140.9300C32—H320.9800
C15—H150.9300C33—Fe12.054 (3)
C16—N31.472 (4)C33—H330.9800
C16—C171.515 (5)C34—C351.422 (5)
C16—H16A0.9700C34—C381.426 (5)
C16—H16B0.9700C34—Fe12.040 (3)
C17—C181.513 (5)C34—H340.9800
C17—H17A0.9700C35—C361.398 (6)
C17—H17B0.9700C35—Fe12.024 (3)
C18—C191.529 (4)C35—H350.9800
C18—H18A0.9700C36—C371.423 (5)
C18—H18B0.9700C36—Fe12.032 (3)
C19—N31.477 (4)C36—H360.9800
C19—C201.530 (4)C37—C381.425 (4)
C19—H190.9800C37—Fe12.052 (3)
C20—C381.503 (4)C37—H370.9800
C20—C211.531 (4)C38—Fe12.060 (3)
N1—C1—C2119.0 (3)C33—C29—H29125.9
N1—C1—C6121.8 (3)C30—C29—H29125.9
C2—C1—C6119.2 (3)Fe1—C29—H29125.9
C3—C2—C1119.8 (4)C31—C30—C29107.4 (4)
C3—C2—H2120.1C31—C30—Fe169.8 (2)
C1—C2—H2120.1C29—C30—Fe169.8 (2)
C2—C3—C4121.1 (4)C31—C30—H30126.3
C2—C3—H3119.5C29—C30—H30126.3
C4—C3—H3119.5Fe1—C30—H30126.3
C5—C4—C3120.5 (4)C30—C31—C32108.4 (4)
C5—C4—H4119.7C30—C31—Fe169.8 (2)
C3—C4—H4119.7C32—C31—Fe170.5 (2)
C4—C5—C6120.2 (4)C30—C31—H31125.8
C4—C5—H5119.9C32—C31—H31125.8
C6—C5—H5119.9Fe1—C31—H31125.8
N2—C6—C5118.9 (3)C33—C32—C31108.0 (4)
N2—C6—C1122.0 (3)C33—C32—Fe170.2 (2)
C5—C6—C1119.2 (3)C31—C32—Fe169.2 (2)
N2—C7—C11123.5 (3)C33—C32—H32126.0
N2—C7—C8125.2 (3)C31—C32—H32126.0
C11—C7—C8111.3 (2)Fe1—C32—H32126.0
N3—C8—C7109.5 (2)C29—C33—C32108.0 (4)
N3—C8—C9114.8 (2)C29—C33—Fe169.3 (2)
C7—C8—C9100.2 (2)C32—C33—Fe169.7 (2)
N3—C8—C21103.0 (2)C29—C33—H33126.0
C7—C8—C21111.2 (2)C32—C33—H33126.0
C9—C8—C21118.2 (2)Fe1—C33—H33126.0
C15—C9—C10119.1 (3)C35—C34—C38108.1 (3)
C15—C9—C8129.6 (3)C35—C34—Fe168.91 (19)
C10—C9—C8111.1 (2)C38—C34—Fe170.42 (17)
C12—C10—C9121.9 (3)C35—C34—H34126.0
C12—C10—C11129.0 (3)C38—C34—H34126.0
C9—C10—C11109.1 (2)Fe1—C34—H34126.0
N1—C11—C7123.9 (3)C36—C35—C34108.4 (3)
N1—C11—C10128.2 (3)C36—C35—Fe170.2 (2)
C7—C11—C10107.9 (2)C34—C35—Fe170.14 (18)
C13—C12—C10118.3 (3)C36—C35—H35125.8
C13—C12—H12120.8C34—C35—H35125.8
C10—C12—H12120.8Fe1—C35—H35125.8
C14—C13—C12120.0 (3)C35—C36—C37108.3 (3)
C14—C13—H13120.0C35—C36—Fe169.5 (2)
C12—C13—H13120.0C37—C36—Fe170.37 (18)
C13—C14—C15122.0 (3)C35—C36—H36125.8
C13—C14—H14119.0C37—C36—H36125.8
C15—C14—H14119.0Fe1—C36—H36125.8
C9—C15—C14118.7 (3)C36—C37—C38108.1 (3)
C9—C15—H15120.7C36—C37—Fe168.9 (2)
C14—C15—H15120.7C38—C37—Fe170.04 (18)
N3—C16—C17105.6 (2)C36—C37—H37125.9
N3—C16—H16A110.6C38—C37—H37125.9
C17—C16—H16A110.6Fe1—C37—H37125.9
N3—C16—H16B110.6C37—C38—C34107.1 (3)
C17—C16—H16B110.6C37—C38—C20127.8 (3)
H16A—C16—H16B108.8C34—C38—C20125.0 (3)
C18—C17—C16102.0 (3)C37—C38—Fe169.41 (18)
C18—C17—H17A111.4C34—C38—Fe168.89 (17)
C16—C17—H17A111.4C20—C38—Fe1128.3 (2)
C18—C17—H17B111.4C11—N1—C1114.2 (3)
C16—C17—H17B111.4C7—N2—C6114.5 (3)
H17A—C17—H17B109.2C16—N3—C19108.0 (2)
C17—C18—C19104.5 (3)C16—N3—C8120.4 (2)
C17—C18—H18A110.9C19—N3—C8111.3 (2)
C19—C18—H18A110.9C35—Fe1—C31104.76 (16)
C17—C18—H18B110.9C35—Fe1—C30118.40 (17)
C19—C18—H18B110.9C31—Fe1—C3040.4 (2)
H18A—C18—H18B108.9C35—Fe1—C3640.32 (16)
N3—C19—C18106.0 (2)C31—Fe1—C36120.97 (17)
N3—C19—C20106.1 (2)C30—Fe1—C36105.07 (17)
C18—C19—C20116.5 (3)C35—Fe1—C29155.23 (17)
N3—C19—H19109.3C31—Fe1—C2967.95 (19)
C18—C19—H19109.3C30—Fe1—C2940.78 (19)
C20—C19—H19109.3C36—Fe1—C29121.61 (18)
C38—C20—C19112.8 (2)C35—Fe1—C3440.95 (13)
C38—C20—C21114.2 (2)C31—Fe1—C34120.64 (18)
C19—C20—C21102.9 (2)C30—Fe1—C34154.82 (18)
C38—C20—H20108.9C36—Fe1—C3468.33 (15)
C19—C20—H20108.9C29—Fe1—C34163.11 (16)
C21—C20—H20108.9C35—Fe1—C32123.07 (17)
C22—C21—C20114.3 (2)C31—Fe1—C3240.32 (17)
C22—C21—C8114.8 (2)C30—Fe1—C3267.89 (19)
C20—C21—C8104.6 (2)C36—Fe1—C32158.00 (16)
C22—C21—H21107.6C29—Fe1—C3267.54 (18)
C20—C21—H21107.6C34—Fe1—C32108.66 (16)
C8—C21—H21107.6C35—Fe1—C3768.24 (15)
O1—C22—C23120.2 (3)C31—Fe1—C37158.56 (17)
O1—C22—C21120.5 (3)C30—Fe1—C37123.57 (19)
C23—C22—C21119.3 (3)C36—Fe1—C3740.77 (14)
C28—C23—C24118.2 (3)C29—Fe1—C37109.45 (17)
C28—C23—C22123.2 (3)C34—Fe1—C3768.17 (14)
C24—C23—C22118.6 (3)C32—Fe1—C37160.23 (15)
C25—C24—C23120.1 (4)C35—Fe1—C33160.93 (17)
C25—C24—H24120.0C31—Fe1—C3367.63 (15)
C23—C24—H24120.0C30—Fe1—C3367.94 (17)
C26—C25—C24119.9 (4)C36—Fe1—C33158.65 (17)
C26—C25—H25120.0C29—Fe1—C3340.09 (17)
C24—C25—H25120.0C34—Fe1—C33126.52 (15)
C27—C26—C25121.1 (4)C32—Fe1—C3340.02 (16)
C27—C26—Br1118.6 (4)C37—Fe1—C33125.08 (15)
C25—C26—Br1120.3 (3)C35—Fe1—C3868.70 (13)
C26—C27—C28119.4 (4)C31—Fe1—C38157.77 (19)
C26—C27—H27120.3C30—Fe1—C38161.55 (19)
C28—C27—H27120.3C36—Fe1—C3868.57 (13)
C27—C28—C23121.3 (4)C29—Fe1—C38126.66 (16)
C27—C28—H28119.4C34—Fe1—C3840.69 (13)
C23—C28—H28119.4C32—Fe1—C38124.33 (14)
C33—C29—C30108.1 (4)C37—Fe1—C3840.55 (13)
C33—C29—Fe170.6 (2)C33—Fe1—C38111.35 (13)
C30—C29—Fe169.4 (2)
N1—C1—C2—C3178.6 (4)C30—C31—Fe1—C35116.7 (3)
C6—C1—C2—C31.2 (7)C32—C31—Fe1—C35124.2 (3)
C1—C2—C3—C40.1 (8)C32—C31—Fe1—C30119.1 (4)
C2—C3—C4—C50.4 (9)C30—C31—Fe1—C3676.3 (3)
C3—C4—C5—C60.4 (8)C32—C31—Fe1—C36164.6 (2)
C4—C5—C6—N2179.0 (4)C30—C31—Fe1—C2938.3 (3)
C4—C5—C6—C11.6 (6)C32—C31—Fe1—C2980.8 (3)
N1—C1—C6—N21.5 (5)C30—C31—Fe1—C34157.9 (2)
C2—C1—C6—N2178.6 (3)C32—C31—Fe1—C3482.9 (3)
N1—C1—C6—C5177.8 (3)C30—C31—Fe1—C32119.1 (4)
C2—C1—C6—C52.0 (5)C30—C31—Fe1—C3748.9 (5)
N2—C7—C8—N364.2 (4)C32—C31—Fe1—C37168.0 (4)
C11—C7—C8—N3115.6 (3)C30—C31—Fe1—C3381.8 (3)
N2—C7—C8—C9174.8 (3)C32—C31—Fe1—C3337.4 (3)
C11—C7—C8—C95.5 (3)C30—C31—Fe1—C38173.7 (3)
N2—C7—C8—C2149.0 (4)C32—C31—Fe1—C3854.6 (5)
C11—C7—C8—C21131.3 (3)C31—C30—Fe1—C3579.1 (3)
N3—C8—C9—C1564.3 (4)C29—C30—Fe1—C35162.5 (3)
C7—C8—C9—C15178.5 (3)C29—C30—Fe1—C31118.4 (4)
C21—C8—C9—C1557.5 (4)C31—C30—Fe1—C36120.4 (3)
N3—C8—C9—C10110.9 (3)C29—C30—Fe1—C36121.3 (3)
C7—C8—C9—C106.3 (3)C31—C30—Fe1—C29118.4 (4)
C21—C8—C9—C10127.2 (3)C31—C30—Fe1—C3449.4 (5)
C15—C9—C10—C121.2 (5)C29—C30—Fe1—C34167.8 (3)
C8—C9—C10—C12174.6 (3)C31—C30—Fe1—C3237.6 (2)
C15—C9—C10—C11179.2 (3)C29—C30—Fe1—C3280.8 (3)
C8—C9—C10—C115.0 (3)C31—C30—Fe1—C37160.7 (2)
N2—C7—C11—N12.2 (5)C29—C30—Fe1—C3780.9 (3)
C8—C7—C11—N1177.5 (3)C31—C30—Fe1—C3380.9 (3)
N2—C7—C11—C10177.3 (3)C29—C30—Fe1—C3337.4 (3)
C8—C7—C11—C102.9 (3)C31—C30—Fe1—C38172.5 (4)
C12—C10—C11—N12.3 (6)C29—C30—Fe1—C3854.1 (6)
C9—C10—C11—N1178.2 (3)C37—C36—Fe1—C35119.3 (3)
C12—C10—C11—C7178.2 (3)C35—C36—Fe1—C3175.6 (3)
C9—C10—C11—C71.3 (3)C37—C36—Fe1—C31165.1 (2)
C9—C10—C12—C130.0 (5)C35—C36—Fe1—C30116.3 (3)
C11—C10—C12—C13179.5 (3)C37—C36—Fe1—C30124.4 (3)
C10—C12—C13—C141.0 (5)C35—C36—Fe1—C29157.3 (2)
C12—C13—C14—C150.7 (5)C37—C36—Fe1—C2983.4 (3)
C10—C9—C15—C141.5 (5)C35—C36—Fe1—C3438.0 (2)
C8—C9—C15—C14173.4 (3)C37—C36—Fe1—C3481.3 (2)
C13—C14—C15—C90.5 (5)C35—C36—Fe1—C3248.3 (5)
N3—C16—C17—C1836.3 (3)C37—C36—Fe1—C32167.6 (4)
C16—C17—C18—C1935.3 (3)C35—C36—Fe1—C37119.3 (3)
C17—C18—C19—N321.9 (3)C35—C36—Fe1—C33175.9 (4)
C17—C18—C19—C2095.8 (3)C37—C36—Fe1—C3356.7 (5)
N3—C19—C20—C38150.8 (2)C35—C36—Fe1—C3881.9 (2)
C18—C19—C20—C3891.6 (3)C37—C36—Fe1—C3837.4 (2)
N3—C19—C20—C2127.1 (3)C33—C29—Fe1—C35158.2 (4)
C18—C19—C20—C21144.8 (2)C30—C29—Fe1—C3539.2 (6)
C38—C20—C21—C2276.1 (3)C33—C29—Fe1—C3181.0 (3)
C19—C20—C21—C22161.2 (2)C30—C29—Fe1—C3138.0 (3)
C38—C20—C21—C8157.6 (2)C33—C29—Fe1—C30119.0 (4)
C19—C20—C21—C834.9 (3)C33—C29—Fe1—C36165.3 (2)
N3—C8—C21—C22155.6 (2)C30—C29—Fe1—C3675.8 (3)
C7—C8—C21—C2287.2 (3)C33—C29—Fe1—C3443.0 (7)
C9—C8—C21—C2227.9 (4)C30—C29—Fe1—C34161.9 (5)
N3—C8—C21—C2029.5 (3)C33—C29—Fe1—C3237.3 (2)
C7—C8—C21—C20146.8 (2)C30—C29—Fe1—C3281.7 (3)
C9—C8—C21—C2098.2 (3)C33—C29—Fe1—C37121.8 (2)
C20—C21—C22—O136.7 (4)C30—C29—Fe1—C37119.2 (3)
C8—C21—C22—O184.2 (4)C30—C29—Fe1—C33119.0 (4)
C20—C21—C22—C23142.0 (3)C33—C29—Fe1—C3879.7 (3)
C8—C21—C22—C2397.1 (3)C30—C29—Fe1—C38161.4 (3)
O1—C22—C23—C28179.9 (3)C38—C34—Fe1—C35119.3 (3)
C21—C22—C23—C281.4 (5)C35—C34—Fe1—C3176.6 (3)
O1—C22—C23—C240.9 (5)C38—C34—Fe1—C31164.0 (2)
C21—C22—C23—C24177.8 (3)C35—C34—Fe1—C3041.7 (5)
C28—C23—C24—C250.1 (5)C38—C34—Fe1—C30161.1 (4)
C22—C23—C24—C25179.2 (3)C35—C34—Fe1—C3637.4 (2)
C23—C24—C25—C260.8 (6)C38—C34—Fe1—C3681.9 (2)
C24—C25—C26—C271.3 (7)C35—C34—Fe1—C29166.7 (6)
C24—C25—C26—Br1179.2 (3)C38—C34—Fe1—C2947.3 (6)
C25—C26—C27—C280.8 (6)C35—C34—Fe1—C32119.3 (2)
Br1—C26—C27—C28179.7 (3)C38—C34—Fe1—C32121.3 (2)
C26—C27—C28—C230.1 (6)C35—C34—Fe1—C3781.5 (2)
C24—C23—C28—C270.6 (5)C38—C34—Fe1—C3737.85 (18)
C22—C23—C28—C27178.7 (3)C35—C34—Fe1—C33160.2 (2)
C33—C29—C30—C310.3 (5)C38—C34—Fe1—C3380.4 (2)
Fe1—C29—C30—C3159.9 (3)C35—C34—Fe1—C38119.3 (3)
C33—C29—C30—Fe160.3 (3)C33—C32—Fe1—C35168.1 (2)
C29—C30—C31—C320.2 (5)C31—C32—Fe1—C3572.7 (3)
Fe1—C30—C31—C3260.2 (3)C33—C32—Fe1—C31119.2 (4)
C29—C30—C31—Fe160.0 (3)C33—C32—Fe1—C3081.6 (3)
C30—C31—C32—C330.0 (4)C31—C32—Fe1—C3037.7 (3)
Fe1—C31—C32—C3359.7 (2)C33—C32—Fe1—C36156.7 (4)
C30—C31—C32—Fe159.8 (3)C31—C32—Fe1—C3637.5 (6)
C30—C29—C33—C320.3 (4)C33—C32—Fe1—C2937.3 (2)
Fe1—C29—C33—C3259.2 (2)C31—C32—Fe1—C2981.9 (3)
C30—C29—C33—Fe159.5 (3)C33—C32—Fe1—C34125.1 (2)
C31—C32—C33—C290.2 (4)C31—C32—Fe1—C34115.7 (3)
Fe1—C32—C33—C2958.9 (3)C33—C32—Fe1—C3747.8 (6)
C31—C32—C33—Fe159.1 (3)C31—C32—Fe1—C37167.1 (4)
C38—C34—C35—C360.2 (4)C31—C32—Fe1—C33119.2 (4)
Fe1—C34—C35—C3660.0 (2)C33—C32—Fe1—C3882.7 (3)
C38—C34—C35—Fe159.8 (2)C31—C32—Fe1—C38158.1 (3)
C34—C35—C36—C370.0 (4)C36—C37—Fe1—C3537.4 (2)
Fe1—C35—C36—C3759.9 (2)C38—C37—Fe1—C3582.2 (2)
C34—C35—C36—Fe160.0 (2)C36—C37—Fe1—C3137.1 (5)
C35—C36—C37—C380.2 (4)C38—C37—Fe1—C31156.8 (4)
Fe1—C36—C37—C3859.2 (2)C36—C37—Fe1—C3073.0 (3)
C35—C36—C37—Fe159.4 (2)C38—C37—Fe1—C30167.3 (2)
C36—C37—C38—C340.3 (4)C38—C37—Fe1—C36119.7 (3)
Fe1—C37—C38—C3458.8 (2)C36—C37—Fe1—C29116.2 (3)
C36—C37—C38—C20178.4 (3)C38—C37—Fe1—C29124.1 (2)
Fe1—C37—C38—C20123.1 (3)C36—C37—Fe1—C3481.7 (2)
C36—C37—C38—Fe158.5 (2)C38—C37—Fe1—C3437.98 (18)
C35—C34—C38—C370.3 (3)C36—C37—Fe1—C32166.2 (4)
Fe1—C34—C38—C3759.1 (2)C38—C37—Fe1—C3246.6 (5)
C35—C34—C38—C20178.5 (3)C36—C37—Fe1—C33158.2 (2)
Fe1—C34—C38—C20122.7 (3)C38—C37—Fe1—C3382.2 (2)
C35—C34—C38—Fe158.8 (2)C36—C37—Fe1—C38119.7 (3)
C19—C20—C38—C37152.6 (3)C29—C33—Fe1—C35151.5 (4)
C21—C20—C38—C3735.4 (4)C32—C33—Fe1—C3532.0 (5)
C19—C20—C38—C3429.6 (4)C29—C33—Fe1—C3181.9 (3)
C21—C20—C38—C34146.8 (3)C32—C33—Fe1—C3137.6 (3)
C19—C20—C38—Fe160.0 (3)C29—C33—Fe1—C3038.1 (3)
C21—C20—C38—Fe157.2 (4)C32—C33—Fe1—C3081.4 (3)
C7—C11—N1—C11.2 (5)C29—C33—Fe1—C3636.5 (5)
C10—C11—N1—C1178.2 (3)C32—C33—Fe1—C36156.0 (4)
C2—C1—N1—C11179.6 (3)C32—C33—Fe1—C29119.5 (3)
C6—C1—N1—C110.5 (5)C29—C33—Fe1—C34165.7 (2)
C11—C7—N2—C61.1 (4)C32—C33—Fe1—C3474.8 (3)
C8—C7—N2—C6178.6 (3)C29—C33—Fe1—C32119.5 (3)
C5—C6—N2—C7178.7 (3)C29—C33—Fe1—C3778.3 (3)
C1—C6—N2—C70.6 (4)C32—C33—Fe1—C37162.2 (2)
C17—C16—N3—C1923.4 (3)C29—C33—Fe1—C38122.1 (3)
C17—C16—N3—C8105.9 (3)C32—C33—Fe1—C38118.4 (2)
C18—C19—N3—C160.9 (3)C37—C38—Fe1—C3581.0 (2)
C20—C19—N3—C16125.3 (3)C34—C38—Fe1—C3537.8 (2)
C18—C19—N3—C8133.4 (3)C20—C38—Fe1—C35156.4 (3)
C20—C19—N3—C88.9 (3)C37—C38—Fe1—C31157.6 (4)
C7—C8—N3—C16101.0 (3)C34—C38—Fe1—C3138.8 (4)
C9—C8—N3—C1610.7 (4)C20—C38—Fe1—C3179.8 (5)
C21—C8—N3—C16140.6 (3)C37—C38—Fe1—C3035.4 (5)
C7—C8—N3—C19131.2 (2)C34—C38—Fe1—C30154.2 (5)
C9—C8—N3—C19117.1 (3)C20—C38—Fe1—C3087.2 (6)
C21—C8—N3—C1912.8 (3)C37—C38—Fe1—C3637.6 (2)
C36—C35—Fe1—C31120.8 (3)C34—C38—Fe1—C3681.3 (2)
C34—C35—Fe1—C31120.0 (3)C20—C38—Fe1—C36160.1 (3)
C36—C35—Fe1—C3079.6 (3)C37—C38—Fe1—C2976.6 (3)
C34—C35—Fe1—C30161.2 (3)C34—C38—Fe1—C29164.6 (2)
C34—C35—Fe1—C36119.2 (3)C20—C38—Fe1—C2945.9 (4)
C36—C35—Fe1—C2951.6 (5)C37—C38—Fe1—C34118.8 (3)
C34—C35—Fe1—C29170.8 (4)C20—C38—Fe1—C34118.6 (4)
C36—C35—Fe1—C34119.2 (3)C37—C38—Fe1—C32162.7 (2)
C36—C35—Fe1—C32160.5 (2)C34—C38—Fe1—C3278.5 (2)
C34—C35—Fe1—C3280.3 (3)C20—C38—Fe1—C3240.2 (3)
C36—C35—Fe1—C3737.8 (2)C34—C38—Fe1—C37118.8 (3)
C34—C35—Fe1—C3781.3 (2)C20—C38—Fe1—C37122.5 (4)
C36—C35—Fe1—C33175.5 (4)C37—C38—Fe1—C33119.5 (2)
C34—C35—Fe1—C3356.3 (5)C34—C38—Fe1—C33121.7 (2)
C36—C35—Fe1—C3881.6 (2)C20—C38—Fe1—C333.1 (3)
C34—C35—Fe1—C3837.6 (2)
Hydrogen-bond geometry (Å, º) top
Cg1, Cg2 and Cg3 are the centroids of the C29–C33, C9–C15 and N1/N2/C1/C6/C7/C11 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C28—H28···N20.932.563.358 (5)145
C13—H13···O1i0.932.583.318 (4)137
C4—H4···Cg1ii0.932.693.580 (4)159
C17—H17B···Cg2iii0.972.843.743 (4)155
C36—H36···Cg3iv0.982.703.486 (5)137
Symmetry codes: (i) x+1, y, z+2; (ii) x+1, y+1, z+1; (iii) x+1, y+1, z+2; (iv) x1, y, z.
Hydrogen-bond geometry (Å, º) top
Cg1, Cg2 and Cg3 are the centroids of the C29–C33, C9–C15 and N1/N2/C1/C6/C7/C11 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C28—H28···N20.932.563.358 (5)145
C13—H13···O1i0.932.583.318 (4)137
C4—H4···Cg1ii0.932.693.580 (4)159
C17—H17B···Cg2iii0.972.843.743 (4)155
C36—H36···Cg3iv0.9812.703.486 (5)137
Symmetry codes: (i) x+1, y, z+2; (ii) x+1, y+1, z+1; (iii) x+1, y+1, z+2; (iv) x1, y, z.
 

Acknowledgements

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

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Volume 69| Part 9| September 2013| Pages m512-m513
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