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 11| November 2012| Pages m1382-m1383

3′-Ferrocenylcarbon­yl-1′-methyl-4′-phenyl­spiro­[indeno­[2,3-b]quinoxaline-11,2′-pyrrolidine]

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 11 August 2012; accepted 10 October 2012; online 20 October 2012)

In the title compound, [Fe(C5H5)(C31H24N3O)], the pyrrolidine ring makes a dihedral angle of 86.3 (3)° with the mean plane [r.m.s deviation = 0.074 (2) Å] of the indeno-quinoxaline ring system. The central pyrrolidine ring adopts a twist conformation and the two cyclopentadienyl rings adopt an eclipsed conformation. In the crystal, mol­ecules are linked by weak C—H⋯N and C—H⋯π inter­actions, propagating along the c and a axes, respectively.

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: Satis Kumar et al. (2007[Satis Kumar, B. K., Gayathri, D., Velmurugan, D., Ravikumar, K. & Sureshbabu, A. R. (2007). Acta Cryst. E63, m1287-m1289.]); 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, m1274.]). 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 /n

  • a = 11.1008 (4) Å

  • b = 11.9156 (5) Å

  • c = 21.0511 (9) Å

  • β = 90.944 (2)°

  • V = 2784.11 (19) 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 APEX2 area-detector diffractometer

  • 26663 measured reflections

  • 7107 independent reflections

  • 4920 reflections with I > 2σ(I)

  • Rint = 0.027

Refinement
  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 0.105

  • S = 1.00

  • 7107 reflections

  • 370 parameters

  • H-atom parameters constrained

  • Δρmax = 0.34 e Å−3

  • Δρmin = −0.31 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C20–C25 ring.

D—H⋯A D—H H⋯A DA D—H⋯A
C31—H31⋯N3i 0.98 2.45 3.430 (2) 176
C1—H1⋯Cg1ii 0.93 2.83 3.650 (2) 147
Symmetry codes: (i) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) -x+1, -y, -z.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. 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, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); 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 derivatives are well known to have biological activities like antitumor (Jaouen et al., 2004), antimalarial and antifungal (Biot et al., 2004), and antibacterial (Fouda et al., 2007). Against this background and in order to obtain detailed information on molecular conformations in the solid state, X-ray diffraction study of the title compound was carried out.

In the title compound (Fig. 1) the pyrrolidine ring adopts a twisted conformation with the puckering parameters q2 and ϕ and the smallest displacement asymmetric parameters, ϕ, as follows: q2 = 0.392 (2) Å, ϕ = 162.8 (3)° and Δ2(C16) = 1.84 (2)°. The indeno-quinoxaline unit is essentially planar, with a mean deviation of 0.074 (2) Å from the least-squares plane defined by the seventeen constituent atoms. The dihedral angle between the pyrrolidine ring (C11/C16–C18/N3) and the plane of indeno-quinoxaline fragment (C1–C6/N1/N2/C7–C15) is 86.3 (3)°. The Fe1···Cg2 and Fe1···Cg3 distances are 1.6461 (8) and 1.6506 (10) Å, respectively and the Cg2···Fe1···Cg3 angle is 177.91 (6)°, where Cg2 and Cg3 are the centroids of the C27–C31 and C32–C36 cyclopentadinene rings, respectively. In the crystal structure (Fig. 2), molecules are connected by weak C—H···N and C—H···π interactions (Table 1, Cg1 is the centroid of the C20–C25 phenyl ring).

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: Satis Kumar et al. (2007); Gunasekaran et al. (2010); Vijayakumar et al. (2012). For puckering and asymmetry parameters, see: Cremer & Pople (1975); Nardelli (1983).

Experimental top

A mixture of ninhydrin (1 mM) and 1,2-phenylenediamine (1 mM) was stirred with 10 ml 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 = 0.93Å and refined using the riding model approximation with a fixed isotropic displacement parameter of 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 (Farrugia, 1997); 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 with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as small spheres of arbitrary radius.
[Figure 2] Fig. 2. A view of the C—H···N and C—H···π interactions (dotted lines) in the crystal structure of the title compound. H atoms non-participating in hydrogen-bonding were omitted for clarity. [Symmetry codes: (i) -x + 3/2, y + 1/2, -z + 1/2; (ii) -x + 1, -y, -z.]
3'-Ferrocenylcarbonyl-1'-methyl-4'-phenylspiro[indeno[2,3- b]quinoxaline-11,2'-pyrrolidine] top
Crystal data top
[Fe(C5H5)(C31H24N3O)]F(000) = 1200
Mr = 575.47Dx = 1.373 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 7107 reflections
a = 11.1008 (4) Åθ = 1.9–28.7°
b = 11.9156 (5) ŵ = 0.58 mm1
c = 21.0511 (9) ÅT = 293 K
β = 90.944 (2)°Block, brown
V = 2784.11 (19) Å30.2 × 0.2 × 0.2 mm
Z = 4
Data collection top
Bruker SMART APEX2 area-detector
diffractometer
4920 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.027
Graphite monochromatorθmax = 28.7°, θmin = 1.9°
ω and ϕ scansh = 1414
26663 measured reflectionsk = 1614
7107 independent reflectionsl = 2822
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)] = 0.038Hydrogen site location: difference Fourier map
wR(F2) = 0.105H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0445P)2 + 1.0601P]
where P = (Fo2 + 2Fc2)/3
7107 reflections(Δ/σ)max < 0.001
370 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = 0.31 e Å3
Crystal data top
[Fe(C5H5)(C31H24N3O)]V = 2784.11 (19) Å3
Mr = 575.47Z = 4
Monoclinic, P21/nMo Kα radiation
a = 11.1008 (4) ŵ = 0.58 mm1
b = 11.9156 (5) ÅT = 293 K
c = 21.0511 (9) Å0.2 × 0.2 × 0.2 mm
β = 90.944 (2)°
Data collection top
Bruker SMART APEX2 area-detector
diffractometer
4920 reflections with I > 2σ(I)
26663 measured reflectionsRint = 0.027
7107 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.105H-atom parameters constrained
S = 1.00Δρmax = 0.34 e Å3
7107 reflectionsΔρmin = 0.31 e Å3
370 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
C10.77481 (19)0.11847 (19)0.10565 (10)0.0523 (5)
H10.71050.07040.09830.063*
C20.8184 (2)0.1304 (2)0.16573 (10)0.0639 (7)
H20.78420.08960.19910.077*
C30.9136 (2)0.2032 (2)0.17707 (11)0.0683 (7)
H30.94290.20990.21800.082*
C40.9646 (2)0.2648 (2)0.12949 (11)0.0654 (7)
H41.02670.31460.13830.079*
C50.92353 (18)0.25338 (18)0.06672 (10)0.0493 (5)
C60.82739 (17)0.17886 (17)0.05517 (9)0.0433 (4)
C70.84103 (15)0.21853 (15)0.04944 (9)0.0375 (4)
C80.93787 (16)0.29346 (16)0.03778 (10)0.0427 (4)
C90.98033 (16)0.33888 (16)0.09867 (10)0.0446 (5)
C100.91387 (15)0.28947 (16)0.14705 (9)0.0393 (4)
C110.81387 (15)0.21463 (15)0.12047 (8)0.0344 (4)
C120.94162 (17)0.31364 (18)0.20968 (10)0.0490 (5)
H120.90040.27880.24230.059*
C131.03199 (19)0.3908 (2)0.22318 (12)0.0606 (6)
H131.05090.40800.26530.073*
C141.0946 (2)0.4425 (2)0.17492 (14)0.0661 (7)
H141.15330.49560.18490.079*
C151.07068 (18)0.41605 (19)0.11241 (13)0.0601 (6)
H151.11420.44920.08000.072*
C160.68110 (14)0.25706 (14)0.13186 (8)0.0319 (4)
H160.64700.28280.09120.038*
C170.60983 (15)0.15244 (15)0.15325 (9)0.0377 (4)
H170.59960.15670.19930.045*
C180.69421 (17)0.05554 (16)0.13916 (10)0.0433 (4)
H18A0.68030.00710.16750.052*
H18B0.68440.03030.09560.052*
C190.91265 (19)0.03021 (19)0.13435 (12)0.0611 (6)
H19A0.98750.06820.14280.092*
H19B0.90740.01060.09020.092*
H19C0.90890.03670.15970.092*
C200.48572 (16)0.14804 (15)0.12174 (10)0.0422 (4)
C210.38282 (18)0.16230 (18)0.15700 (12)0.0574 (6)
H210.38890.16620.20110.069*
C220.2701 (2)0.1709 (2)0.12730 (16)0.0743 (8)
H220.20190.18220.15160.089*
C230.2592 (2)0.1628 (2)0.06276 (17)0.0775 (8)
H230.18400.16940.04300.093*
C240.3599 (2)0.1448 (2)0.02715 (13)0.0665 (7)
H240.35260.13720.01670.080*
C250.47266 (19)0.13794 (18)0.05648 (11)0.0522 (5)
H250.54040.12640.03190.063*
C260.67864 (14)0.35423 (15)0.17847 (8)0.0334 (4)
C270.70406 (14)0.46598 (15)0.15256 (8)0.0338 (4)
C280.71680 (15)0.49567 (16)0.08699 (9)0.0386 (4)
H280.71840.44350.05100.046*
C290.72666 (18)0.61355 (18)0.08356 (10)0.0495 (5)
H290.73440.65780.04460.059*
C300.72074 (18)0.65705 (17)0.14583 (11)0.0503 (5)
H300.72340.73680.15720.060*
C310.70684 (16)0.56730 (16)0.18877 (9)0.0416 (4)
H310.70050.57340.23500.050*
C320.41038 (19)0.4857 (3)0.14284 (15)0.0736 (8)
H320.40280.41070.16150.088*
C330.4164 (2)0.5871 (4)0.17646 (15)0.0895 (10)
H330.41300.59600.22270.107*
C340.4264 (2)0.6725 (3)0.1322 (2)0.0933 (11)
H340.43190.75280.14210.112*
C350.4259 (2)0.6263 (3)0.07184 (15)0.0805 (8)
H350.43130.66790.03180.097*
C360.41605 (19)0.5102 (2)0.07812 (13)0.0672 (7)
H360.41370.45550.04330.081*
N10.78365 (14)0.16272 (13)0.00513 (7)0.0405 (4)
N20.97974 (15)0.31325 (16)0.01893 (9)0.0536 (4)
N30.81296 (13)0.10361 (13)0.15009 (7)0.0407 (4)
O10.65943 (13)0.33960 (12)0.23460 (6)0.0482 (3)
Fe10.56726 (2)0.56669 (2)0.124750 (13)0.03939 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0551 (12)0.0581 (13)0.0439 (12)0.0195 (10)0.0050 (9)0.0000 (10)
C20.0678 (15)0.0819 (18)0.0420 (12)0.0347 (14)0.0023 (10)0.0004 (12)
C30.0685 (15)0.0936 (19)0.0435 (13)0.0377 (14)0.0174 (11)0.0164 (13)
C40.0572 (13)0.0820 (18)0.0577 (15)0.0201 (12)0.0216 (11)0.0225 (13)
C50.0432 (10)0.0556 (13)0.0497 (12)0.0170 (9)0.0140 (9)0.0113 (10)
C60.0434 (10)0.0452 (11)0.0414 (10)0.0182 (8)0.0078 (8)0.0061 (9)
C70.0330 (8)0.0362 (10)0.0434 (10)0.0087 (7)0.0077 (7)0.0053 (8)
C80.0336 (9)0.0404 (10)0.0543 (12)0.0059 (8)0.0107 (8)0.0096 (9)
C90.0306 (9)0.0417 (11)0.0615 (13)0.0037 (8)0.0045 (8)0.0042 (9)
C100.0279 (8)0.0385 (10)0.0514 (11)0.0056 (7)0.0009 (7)0.0031 (8)
C110.0316 (8)0.0339 (9)0.0378 (9)0.0045 (7)0.0026 (7)0.0028 (7)
C120.0374 (10)0.0531 (12)0.0564 (12)0.0010 (9)0.0065 (9)0.0032 (10)
C130.0466 (11)0.0628 (14)0.0717 (15)0.0017 (11)0.0159 (11)0.0051 (12)
C140.0420 (11)0.0597 (15)0.096 (2)0.0083 (10)0.0108 (12)0.0055 (14)
C150.0394 (11)0.0545 (14)0.0867 (18)0.0055 (9)0.0071 (11)0.0078 (12)
C160.0299 (8)0.0332 (9)0.0327 (9)0.0012 (7)0.0025 (7)0.0034 (7)
C170.0371 (9)0.0377 (10)0.0385 (10)0.0044 (7)0.0038 (7)0.0013 (8)
C180.0472 (10)0.0340 (10)0.0488 (11)0.0009 (8)0.0002 (8)0.0074 (8)
C190.0513 (12)0.0470 (12)0.0850 (17)0.0180 (10)0.0033 (11)0.0110 (12)
C200.0355 (9)0.0340 (10)0.0571 (12)0.0054 (7)0.0025 (8)0.0009 (9)
C210.0443 (11)0.0502 (13)0.0781 (16)0.0082 (9)0.0112 (11)0.0151 (11)
C220.0372 (11)0.0623 (16)0.124 (2)0.0028 (10)0.0095 (13)0.0171 (16)
C230.0457 (13)0.0585 (16)0.128 (3)0.0015 (11)0.0218 (15)0.0000 (16)
C240.0657 (15)0.0541 (14)0.0789 (17)0.0064 (11)0.0237 (13)0.0039 (12)
C250.0477 (11)0.0501 (12)0.0586 (13)0.0039 (9)0.0048 (9)0.0019 (10)
C260.0275 (8)0.0391 (10)0.0338 (9)0.0038 (7)0.0000 (6)0.0002 (7)
C270.0288 (8)0.0362 (9)0.0362 (9)0.0031 (7)0.0007 (7)0.0018 (7)
C280.0363 (9)0.0404 (10)0.0392 (10)0.0027 (8)0.0042 (7)0.0004 (8)
C290.0471 (11)0.0432 (11)0.0585 (13)0.0021 (9)0.0059 (9)0.0116 (10)
C300.0491 (11)0.0350 (10)0.0669 (14)0.0044 (9)0.0014 (10)0.0063 (10)
C310.0367 (9)0.0420 (10)0.0459 (11)0.0007 (8)0.0044 (8)0.0069 (9)
C320.0334 (11)0.089 (2)0.099 (2)0.0029 (12)0.0050 (12)0.0158 (17)
C330.0390 (12)0.150 (3)0.080 (2)0.0184 (16)0.0089 (12)0.033 (2)
C340.0580 (16)0.074 (2)0.147 (3)0.0346 (14)0.0232 (18)0.034 (2)
C350.0606 (15)0.086 (2)0.094 (2)0.0177 (14)0.0286 (14)0.0182 (17)
C360.0403 (11)0.0840 (19)0.0768 (17)0.0036 (11)0.0131 (11)0.0211 (15)
N10.0418 (8)0.0402 (9)0.0399 (9)0.0067 (7)0.0073 (7)0.0024 (7)
N20.0442 (9)0.0584 (11)0.0588 (11)0.0042 (8)0.0167 (8)0.0134 (9)
N30.0393 (8)0.0342 (8)0.0485 (9)0.0050 (6)0.0009 (7)0.0080 (7)
O10.0615 (8)0.0496 (8)0.0336 (7)0.0017 (7)0.0078 (6)0.0009 (6)
Fe10.03474 (14)0.03809 (16)0.04522 (17)0.00631 (11)0.00323 (11)0.00167 (12)
Geometric parameters (Å, º) top
C1—C21.369 (3)C20—C211.383 (3)
C1—C61.403 (3)C20—C251.384 (3)
C1—H10.9300C21—C221.393 (3)
C2—C31.392 (4)C21—H210.9300
C2—H20.9300C22—C231.365 (4)
C3—C41.358 (4)C22—H220.9300
C3—H30.9300C23—C241.373 (4)
C4—C51.412 (3)C23—H230.9300
C4—H40.9300C24—C251.389 (3)
C5—N21.375 (3)C24—H240.9300
C5—C61.412 (3)C25—H250.9300
C6—N11.380 (2)C26—O11.217 (2)
C7—N11.303 (2)C26—C271.468 (2)
C7—C81.422 (3)C27—C311.428 (3)
C7—C111.531 (2)C27—C281.434 (2)
C8—N21.310 (2)C27—Fe12.0148 (16)
C8—C91.462 (3)C28—C291.411 (3)
C9—C151.388 (3)C28—Fe12.0364 (17)
C9—C101.397 (3)C28—H280.9800
C10—C121.379 (3)C29—C301.412 (3)
C10—C111.523 (2)C29—Fe12.060 (2)
C11—N31.462 (2)C29—H290.9800
C11—C161.580 (2)C30—C311.410 (3)
C12—C131.387 (3)C30—Fe12.058 (2)
C12—H120.9300C30—H300.9800
C13—C141.385 (3)C31—Fe12.0367 (18)
C13—H130.9300C31—H310.9800
C14—C151.375 (3)C32—C361.396 (4)
C14—H140.9300C32—C331.401 (4)
C15—H150.9300C32—Fe12.033 (2)
C16—C261.518 (2)C32—H320.9800
C16—C171.547 (2)C33—C341.385 (5)
C16—H160.9800C33—Fe12.026 (2)
C17—C181.519 (3)C33—H330.9800
C17—C201.520 (2)C34—C351.386 (4)
C17—H170.9800C34—Fe12.017 (2)
C18—N31.452 (2)C34—H340.9800
C18—H18A0.9700C35—C361.395 (4)
C18—H18B0.9700C35—Fe12.037 (2)
C19—N31.453 (2)C35—H350.9800
C19—H19A0.9600C36—Fe12.045 (2)
C19—H19B0.9600C36—H360.9800
C19—H19C0.9600
C2—C1—C6119.9 (2)C29—C28—H28126.2
C2—C1—H1120.1C27—C28—H28126.2
C6—C1—H1120.1Fe1—C28—H28126.2
C1—C2—C3120.3 (2)C28—C29—C30108.25 (18)
C1—C2—H2119.9C28—C29—Fe168.95 (11)
C3—C2—H2119.9C30—C29—Fe169.84 (11)
C4—C3—C2121.3 (2)C28—C29—H29125.9
C4—C3—H3119.4C30—C29—H29125.9
C2—C3—H3119.4Fe1—C29—H29125.9
C3—C4—C5120.1 (2)C31—C30—C29108.90 (18)
C3—C4—H4120.0C31—C30—Fe169.05 (11)
C5—C4—H4120.0C29—C30—Fe170.05 (11)
N2—C5—C4119.0 (2)C31—C30—H30125.5
N2—C5—C6122.38 (18)C29—C30—H30125.5
C4—C5—C6118.6 (2)Fe1—C30—H30125.5
N1—C6—C1118.49 (19)C30—C31—C27107.50 (17)
N1—C6—C5121.62 (18)C30—C31—Fe170.65 (11)
C1—C6—C5119.89 (19)C27—C31—Fe168.55 (9)
N1—C7—C8123.99 (17)C30—C31—H31126.2
N1—C7—C11125.57 (16)C27—C31—H31126.2
C8—C7—C11110.44 (16)Fe1—C31—H31126.2
N2—C8—C7123.44 (19)C36—C32—C33108.1 (3)
N2—C8—C9128.20 (18)C36—C32—Fe170.45 (14)
C7—C8—C9108.35 (16)C33—C32—Fe169.57 (15)
C15—C9—C10121.0 (2)C36—C32—H32126.0
C15—C9—C8130.5 (2)C33—C32—H32126.0
C10—C9—C8108.45 (16)Fe1—C32—H32126.0
C12—C10—C9119.76 (18)C34—C33—C32107.4 (3)
C12—C10—C11128.55 (17)C34—C33—Fe169.61 (16)
C9—C10—C11111.67 (16)C32—C33—Fe170.04 (14)
N3—C11—C10112.52 (14)C34—C33—H33126.3
N3—C11—C7116.54 (15)C32—C33—H33126.3
C10—C11—C7100.77 (14)Fe1—C33—H33126.3
N3—C11—C16102.23 (13)C33—C34—C35109.0 (3)
C10—C11—C16115.65 (14)C33—C34—Fe170.33 (15)
C7—C11—C16109.73 (13)C35—C34—Fe170.78 (15)
C10—C12—C13118.9 (2)C33—C34—H34125.5
C10—C12—H12120.5C35—C34—H34125.5
C13—C12—H12120.5Fe1—C34—H34125.5
C14—C13—C12121.0 (2)C34—C35—C36107.9 (3)
C14—C13—H13119.5C34—C35—Fe169.25 (14)
C12—C13—H13119.5C36—C35—Fe170.31 (13)
C15—C14—C13120.6 (2)C34—C35—H35126.1
C15—C14—H14119.7C36—C35—H35126.1
C13—C14—H14119.7Fe1—C35—H35126.1
C14—C15—C9118.6 (2)C35—C36—C32107.7 (3)
C14—C15—H15120.7C35—C36—Fe169.72 (14)
C9—C15—H15120.7C32—C36—Fe169.52 (13)
C26—C16—C17114.31 (14)C35—C36—H36126.1
C26—C16—C11111.65 (13)C32—C36—H36126.1
C17—C16—C11105.60 (13)Fe1—C36—H36126.1
C26—C16—H16108.4C7—N1—C6114.33 (16)
C17—C16—H16108.4C8—N2—C5114.21 (18)
C11—C16—H16108.4C18—N3—C19114.78 (16)
C18—C17—C20116.49 (15)C18—N3—C11107.57 (13)
C18—C17—C16103.63 (14)C19—N3—C11115.88 (16)
C20—C17—C16111.41 (15)C27—Fe1—C34158.62 (13)
C18—C17—H17108.3C27—Fe1—C33122.73 (12)
C20—C17—H17108.3C34—Fe1—C3340.06 (13)
C16—C17—H17108.3C27—Fe1—C32107.86 (10)
N3—C18—C17103.31 (15)C34—Fe1—C3267.33 (13)
N3—C18—H18A111.1C33—Fe1—C3240.39 (12)
C17—C18—H18A111.1C27—Fe1—C2841.46 (7)
N3—C18—H18B111.1C34—Fe1—C28158.17 (14)
C17—C18—H18B111.1C33—Fe1—C28160.99 (13)
H18A—C18—H18B109.1C32—Fe1—C28125.61 (10)
N3—C19—H19A109.5C27—Fe1—C3141.26 (7)
N3—C19—H19B109.5C34—Fe1—C31121.89 (11)
H19A—C19—H19B109.5C33—Fe1—C31105.69 (10)
N3—C19—H19C109.5C32—Fe1—C31121.51 (10)
H19A—C19—H19C109.5C28—Fe1—C3169.12 (8)
H19B—C19—H19C109.5C27—Fe1—C35159.50 (11)
C21—C20—C25118.00 (19)C34—Fe1—C3539.97 (12)
C21—C20—C17120.82 (19)C33—Fe1—C3567.43 (13)
C25—C20—C17121.02 (17)C32—Fe1—C3567.27 (12)
C20—C21—C22120.8 (2)C28—Fe1—C35123.85 (11)
C20—C21—H21119.6C31—Fe1—C35158.63 (11)
C22—C21—H21119.6C27—Fe1—C36123.52 (9)
C23—C22—C21120.3 (2)C34—Fe1—C3667.19 (11)
C23—C22—H22119.8C33—Fe1—C3667.57 (11)
C21—C22—H22119.8C32—Fe1—C3640.04 (10)
C22—C23—C24119.7 (2)C28—Fe1—C36110.11 (9)
C22—C23—H23120.2C31—Fe1—C36158.19 (10)
C24—C23—H23120.2C35—Fe1—C3639.97 (11)
C23—C24—C25120.2 (2)C27—Fe1—C3068.38 (8)
C23—C24—H24119.9C34—Fe1—C30107.22 (11)
C25—C24—H24119.9C33—Fe1—C30120.65 (11)
C20—C25—C24121.0 (2)C32—Fe1—C30156.49 (11)
C20—C25—H25119.5C28—Fe1—C3067.93 (8)
C24—C25—H25119.5C31—Fe1—C3040.29 (8)
O1—C26—C27121.91 (16)C35—Fe1—C30124.26 (11)
O1—C26—C16121.58 (16)C36—Fe1—C30161.12 (11)
C27—C26—C16116.49 (14)C27—Fe1—C2968.61 (8)
C31—C27—C28107.67 (16)C34—Fe1—C29122.39 (13)
C31—C27—C26124.84 (16)C33—Fe1—C29156.40 (13)
C28—C27—C26127.15 (16)C32—Fe1—C29162.17 (11)
C31—C27—Fe170.19 (10)C28—Fe1—C2940.28 (8)
C28—C27—Fe170.08 (10)C31—Fe1—C2968.17 (8)
C26—C27—Fe1119.97 (11)C35—Fe1—C29109.54 (11)
C29—C28—C27107.68 (17)C36—Fe1—C29126.24 (10)
C29—C28—Fe170.77 (11)C30—Fe1—C2940.11 (8)
C27—C28—Fe168.46 (9)
C6—C1—C2—C30.8 (3)C26—C27—Fe1—C30157.15 (16)
C1—C2—C3—C40.7 (3)C31—C27—Fe1—C2980.85 (12)
C2—C3—C4—C51.8 (3)C28—C27—Fe1—C2937.43 (11)
C3—C4—C5—N2177.4 (2)C26—C27—Fe1—C29159.60 (16)
C3—C4—C5—C61.3 (3)C33—C34—Fe1—C2742.9 (4)
C2—C1—C6—N1178.24 (18)C35—C34—Fe1—C27162.2 (2)
C2—C1—C6—C51.2 (3)C35—C34—Fe1—C33119.4 (3)
N2—C5—C6—N10.6 (3)C33—C34—Fe1—C3238.21 (18)
C4—C5—C6—N1179.28 (18)C35—C34—Fe1—C3281.2 (2)
N2—C5—C6—C1178.88 (18)C33—C34—Fe1—C28169.1 (2)
C4—C5—C6—C10.2 (3)C35—C34—Fe1—C2849.7 (4)
N1—C7—C8—N20.5 (3)C33—C34—Fe1—C3175.8 (2)
C11—C7—C8—N2179.79 (17)C35—C34—Fe1—C31164.81 (17)
N1—C7—C8—C9179.20 (16)C33—C34—Fe1—C35119.4 (3)
C11—C7—C8—C91.5 (2)C33—C34—Fe1—C3681.8 (2)
N2—C8—C9—C152.7 (3)C35—C34—Fe1—C3637.59 (19)
C7—C8—C9—C15178.7 (2)C33—C34—Fe1—C30117.43 (19)
N2—C8—C9—C10176.40 (18)C35—C34—Fe1—C30123.20 (19)
C7—C8—C9—C102.2 (2)C33—C34—Fe1—C29158.70 (17)
C15—C9—C10—C122.9 (3)C35—C34—Fe1—C2981.9 (2)
C8—C9—C10—C12176.24 (16)C34—C33—Fe1—C27162.85 (16)
C15—C9—C10—C11175.70 (17)C32—C33—Fe1—C2778.89 (19)
C8—C9—C10—C115.1 (2)C32—C33—Fe1—C34118.3 (3)
C12—C10—C11—N351.0 (2)C34—C33—Fe1—C32118.3 (3)
C9—C10—C11—N3130.52 (16)C34—C33—Fe1—C28167.5 (3)
C12—C10—C11—C7175.86 (18)C32—C33—Fe1—C2849.2 (4)
C9—C10—C11—C75.68 (18)C34—C33—Fe1—C31121.23 (18)
C12—C10—C11—C1665.9 (2)C32—C33—Fe1—C31120.50 (17)
C9—C10—C11—C16112.52 (17)C34—C33—Fe1—C3537.32 (18)
N1—C7—C11—N354.5 (2)C32—C33—Fe1—C3580.95 (19)
C8—C7—C11—N3126.27 (16)C34—C33—Fe1—C3680.7 (2)
N1—C7—C11—C10176.52 (17)C32—C33—Fe1—C3637.53 (17)
C8—C7—C11—C104.21 (18)C34—C33—Fe1—C3080.2 (2)
N1—C7—C11—C1661.1 (2)C32—C33—Fe1—C30161.52 (16)
C8—C7—C11—C16118.22 (16)C34—C33—Fe1—C2950.0 (3)
C9—C10—C12—C132.8 (3)C32—C33—Fe1—C29168.3 (2)
C11—C10—C12—C13175.51 (18)C36—C32—Fe1—C27121.22 (16)
C10—C12—C13—C140.5 (3)C33—C32—Fe1—C27119.86 (19)
C12—C13—C14—C151.8 (4)C36—C32—Fe1—C3481.02 (19)
C13—C14—C15—C91.8 (3)C33—C32—Fe1—C3437.90 (18)
C10—C9—C15—C140.6 (3)C36—C32—Fe1—C33118.9 (3)
C8—C9—C15—C14178.4 (2)C36—C32—Fe1—C2878.75 (18)
N3—C11—C16—C26111.69 (15)C33—C32—Fe1—C28162.33 (18)
C10—C11—C16—C2610.9 (2)C36—C32—Fe1—C31164.43 (14)
C7—C11—C16—C26124.01 (15)C33—C32—Fe1—C3176.6 (2)
N3—C11—C16—C1713.10 (17)C36—C32—Fe1—C3537.53 (17)
C10—C11—C16—C17135.71 (15)C33—C32—Fe1—C3581.4 (2)
C7—C11—C16—C17111.19 (16)C33—C32—Fe1—C36118.9 (3)
C26—C16—C17—C18135.03 (15)C36—C32—Fe1—C30162.1 (2)
C11—C16—C17—C1811.90 (17)C33—C32—Fe1—C3043.1 (3)
C26—C16—C17—C2098.96 (17)C36—C32—Fe1—C2945.7 (4)
C11—C16—C17—C20137.91 (15)C33—C32—Fe1—C29164.6 (3)
C20—C17—C18—N3155.72 (16)C29—C28—Fe1—C27118.92 (16)
C16—C17—C18—N333.00 (18)C29—C28—Fe1—C3444.1 (3)
C18—C17—C20—C21129.3 (2)C27—C28—Fe1—C34163.1 (3)
C16—C17—C20—C21112.1 (2)C29—C28—Fe1—C33157.8 (3)
C18—C17—C20—C2555.5 (2)C27—C28—Fe1—C3338.9 (3)
C16—C17—C20—C2563.1 (2)C29—C28—Fe1—C32165.02 (14)
C25—C20—C21—C222.6 (3)C27—C28—Fe1—C3276.07 (14)
C17—C20—C21—C22172.7 (2)C29—C28—Fe1—C3180.48 (13)
C20—C21—C22—C231.5 (4)C27—C28—Fe1—C3138.44 (10)
C21—C22—C23—C240.7 (4)C29—C28—Fe1—C3580.30 (17)
C22—C23—C24—C251.8 (4)C27—C28—Fe1—C35160.79 (14)
C21—C20—C25—C241.6 (3)C29—C28—Fe1—C36122.81 (14)
C17—C20—C25—C24173.73 (19)C27—C28—Fe1—C36118.28 (13)
C23—C24—C25—C200.6 (3)C29—C28—Fe1—C3037.05 (12)
C17—C16—C26—O123.5 (2)C27—C28—Fe1—C3081.86 (12)
C11—C16—C26—O196.32 (18)C27—C28—Fe1—C29118.92 (16)
C17—C16—C26—C27158.23 (14)C30—C31—Fe1—C27118.71 (16)
C11—C16—C26—C2781.98 (17)C30—C31—Fe1—C3478.78 (19)
O1—C26—C27—C311.2 (3)C27—C31—Fe1—C34162.51 (17)
C16—C26—C27—C31179.50 (15)C30—C31—Fe1—C33119.18 (17)
O1—C26—C27—C28173.65 (16)C27—C31—Fe1—C33122.10 (16)
C16—C26—C27—C288.1 (2)C30—C31—Fe1—C32160.09 (14)
O1—C26—C27—Fe186.89 (18)C27—C31—Fe1—C3281.19 (15)
C16—C26—C27—Fe194.82 (15)C30—C31—Fe1—C2880.10 (12)
C31—C27—C28—C290.24 (19)C27—C31—Fe1—C2838.62 (10)
C26—C27—C28—C29173.25 (16)C30—C31—Fe1—C3551.3 (3)
Fe1—C27—C28—C2960.17 (13)C27—C31—Fe1—C35170.0 (3)
C31—C27—C28—Fe160.41 (12)C30—C31—Fe1—C36172.2 (2)
C26—C27—C28—Fe1113.08 (16)C27—C31—Fe1—C3653.5 (3)
C27—C28—C29—C300.2 (2)C27—C31—Fe1—C30118.71 (16)
Fe1—C28—C29—C3058.96 (14)C30—C31—Fe1—C2936.71 (12)
C27—C28—C29—Fe158.71 (12)C27—C31—Fe1—C2982.00 (12)
C28—C29—C30—C310.2 (2)C34—C35—Fe1—C27161.5 (3)
Fe1—C29—C30—C3158.25 (14)C36—C35—Fe1—C2742.6 (4)
C28—C29—C30—Fe158.40 (13)C36—C35—Fe1—C34118.9 (3)
C29—C30—C31—C270.0 (2)C34—C35—Fe1—C3337.4 (2)
Fe1—C30—C31—C2758.86 (12)C36—C35—Fe1—C3381.5 (2)
C29—C30—C31—Fe158.85 (14)C34—C35—Fe1—C3281.3 (2)
C28—C27—C31—C300.15 (19)C36—C35—Fe1—C3237.59 (17)
C26—C27—C31—C30173.54 (16)C34—C35—Fe1—C28160.03 (19)
Fe1—C27—C31—C3060.19 (13)C36—C35—Fe1—C2881.04 (19)
C28—C27—C31—Fe160.34 (11)C34—C35—Fe1—C3137.6 (4)
C26—C27—C31—Fe1113.35 (16)C36—C35—Fe1—C31156.5 (2)
C36—C32—C33—C340.3 (3)C34—C35—Fe1—C36118.9 (3)
Fe1—C32—C33—C3459.88 (18)C34—C35—Fe1—C3075.2 (2)
C36—C32—C33—Fe160.18 (16)C36—C35—Fe1—C30165.84 (15)
C32—C33—C34—C350.3 (3)C34—C35—Fe1—C29117.5 (2)
Fe1—C33—C34—C3560.48 (19)C36—C35—Fe1—C29123.59 (17)
C32—C33—C34—Fe160.15 (17)C35—C36—Fe1—C27163.49 (17)
C33—C34—C35—C360.2 (3)C32—C36—Fe1—C2777.51 (18)
Fe1—C34—C35—C3659.97 (17)C35—C36—Fe1—C3437.6 (2)
C33—C34—C35—Fe160.20 (18)C32—C36—Fe1—C3481.4 (2)
C34—C35—C36—C320.0 (3)C35—C36—Fe1—C3381.1 (2)
Fe1—C35—C36—C3259.34 (16)C32—C36—Fe1—C3337.85 (19)
C34—C35—C36—Fe159.30 (18)C35—C36—Fe1—C32119.0 (2)
C33—C32—C36—C350.2 (3)C35—C36—Fe1—C28119.12 (18)
Fe1—C32—C36—C3559.47 (17)C32—C36—Fe1—C28121.88 (17)
C33—C32—C36—Fe159.63 (16)C35—C36—Fe1—C31157.0 (2)
C8—C7—N1—C62.2 (2)C32—C36—Fe1—C3138.0 (3)
C11—C7—N1—C6178.60 (15)C32—C36—Fe1—C35119.0 (2)
C1—C6—N1—C7177.24 (17)C35—C36—Fe1—C3038.7 (4)
C5—C6—N1—C72.2 (2)C32—C36—Fe1—C30157.7 (3)
C7—C8—N2—C51.3 (3)C35—C36—Fe1—C2976.8 (2)
C9—C8—N2—C5177.16 (18)C32—C36—Fe1—C29164.24 (16)
C4—C5—N2—C8177.52 (18)C31—C30—Fe1—C2738.48 (11)
C6—C5—N2—C81.2 (3)C29—C30—Fe1—C2782.04 (12)
C17—C18—N3—C19174.78 (16)C31—C30—Fe1—C34119.31 (17)
C17—C18—N3—C1144.20 (18)C29—C30—Fe1—C34120.17 (17)
C10—C11—N3—C18160.03 (15)C31—C30—Fe1—C3377.70 (18)
C7—C11—N3—C1884.29 (18)C29—C30—Fe1—C33161.78 (17)
C16—C11—N3—C1835.34 (17)C31—C30—Fe1—C3246.7 (3)
C10—C11—N3—C1970.0 (2)C29—C30—Fe1—C32167.2 (2)
C7—C11—N3—C1945.7 (2)C31—C30—Fe1—C2883.31 (12)
C16—C11—N3—C19165.29 (16)C29—C30—Fe1—C2837.21 (12)
C31—C27—Fe1—C3444.4 (3)C29—C30—Fe1—C31120.52 (17)
C28—C27—Fe1—C34162.7 (3)C31—C30—Fe1—C35159.88 (15)
C26—C27—Fe1—C3475.1 (3)C29—C30—Fe1—C3579.60 (17)
C31—C27—Fe1—C3375.80 (16)C31—C30—Fe1—C36171.1 (3)
C28—C27—Fe1—C33165.92 (14)C29—C30—Fe1—C3650.5 (3)
C26—C27—Fe1—C3343.75 (19)C31—C30—Fe1—C29120.52 (17)
C31—C27—Fe1—C32117.72 (14)C28—C29—Fe1—C2738.50 (11)
C28—C27—Fe1—C32124.00 (13)C30—C29—Fe1—C2781.42 (13)
C26—C27—Fe1—C321.83 (18)C28—C29—Fe1—C34162.14 (15)
C31—C27—Fe1—C28118.28 (15)C30—C29—Fe1—C3477.94 (17)
C26—C27—Fe1—C28122.17 (18)C28—C29—Fe1—C33162.1 (3)
C28—C27—Fe1—C31118.28 (15)C30—C29—Fe1—C3342.2 (3)
C26—C27—Fe1—C31119.55 (18)C28—C29—Fe1—C3243.3 (4)
C31—C27—Fe1—C35169.6 (3)C30—C29—Fe1—C32163.3 (3)
C28—C27—Fe1—C3551.3 (3)C30—C29—Fe1—C28119.91 (17)
C26—C27—Fe1—C3570.9 (3)C28—C29—Fe1—C3183.04 (12)
C31—C27—Fe1—C36159.01 (13)C30—C29—Fe1—C3136.88 (12)
C28—C27—Fe1—C3682.71 (14)C28—C29—Fe1—C35119.70 (14)
C26—C27—Fe1—C3639.46 (18)C30—C29—Fe1—C35120.39 (15)
C31—C27—Fe1—C3037.60 (11)C28—C29—Fe1—C3678.13 (16)
C28—C27—Fe1—C3080.68 (12)C30—C29—Fe1—C36161.96 (14)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C20–C25 ring.
D—H···AD—HH···AD···AD—H···A
C31—H31···N3i0.982.453.430 (2)176
C1—H1···Cg1ii0.932.833.650 (2)147
Symmetry codes: (i) x+3/2, y+1/2, z+1/2; (ii) x+1, y, z.

Experimental details

Crystal data
Chemical formula[Fe(C5H5)(C31H24N3O)]
Mr575.47
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)11.1008 (4), 11.9156 (5), 21.0511 (9)
β (°) 90.944 (2)
V3)2784.11 (19)
Z4
Radiation typeMo Kα
µ (mm1)0.58
Crystal size (mm)0.2 × 0.2 × 0.2
Data collection
DiffractometerBruker SMART APEX2 area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
26663, 7107, 4920
Rint0.027
(sin θ/λ)max1)0.675
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.105, 1.00
No. of reflections7107
No. of parameters370
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.34, 0.31

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C20–C25 ring.
D—H···AD—HH···AD···AD—H···A
C31—H31···N3i0.982.453.430 (2)176
C1—H1···Cg1ii0.932.833.650 (2)147
Symmetry codes: (i) x+3/2, y+1/2, z+1/2; (ii) x+1, y, z.
 

Acknowledgements

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

References

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Volume 68| Part 11| November 2012| Pages m1382-m1383
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