Bis(4,6-di-tert-butyl-2-{N-[4-(diethylamino)phenyl]- carboximidoyl}phenolato)cobalt(ii)

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1 Bis(4,6-di-tert-butyl-2-{N-[4-(diethylamino)phenyl]- carboximidoyl}phenolato)cobalt(ii) ISSN C.Vidya Rani, a L. Mitu, b G. Chakkaravarthi c * and G. Rajagopal d * Received 23 May 2017 Accepted 26 May 2017 Edited by C. Rizzoli, Universita degli Studi di Parma, Italy Keywords: crystal structure; distorted tetrahedral geometry; cobalt(ii) complex. CCDC reference: Structural data: full structural data are available from iucrdata.iucr.org a Department of Chemistry, Vaigai College of Engineering, Madurai , Tamil Nadu, India, b Department of Chemistry, University of Pitesti, Pitesti 11040, Romania, c Department of Physics, CPCL Polytechnic College, Chennai , India, and d PG & Research Department of Chemistry, Chikkanna Government Arts College, Tiruppur , Tamil Nadu, India. *Correspondence chakkaravarthi_2005@yahoo.com, rajagopal18@yahoo.com In the title complex, [Co(C 25 H 35 N 2 O) 2 ], the cobalt(ii) atom has a distorted tetrahedral geometry provided by pairs of O and N atoms. The dihedral angles between the benzene rings of the same ligand are (9) and (9).The molecular structure is stabilized by weak intramolecular C HO hydrogen bonds. The crystal packing is stabilized mainly by van der Waals forces. The structure contains a solvent-accessible void of 276 Å 3 which was treated using the SQUEEZE routine from PLATON [Spek (2015). Acta Cryst. C71, 9 18]. The methyl C atoms of the tert-butyl groups are rotationally disordered, with site occupancies of (3) and (9) for the major components and (3) and (9) for the minor components. Structure description In our continuing work on the development of new N- and O-chelating ligands able to play a key role in the coordination of metals at the active sites of numerous metallobimolecules (Nair et al., 2006), we herein report on the synthesis and the crystal structure of the title compound (Fig. 1). The cobalt(ii) atom is coordinated in a distorted tetrahedral geometry by two O and two N atoms. The Co O and Co N bond lengths [Co1 O1 = (18), Co1 O2 = (17), Co1 N1 = (2) and Co1 N2 = (2) Å] are similar to those reported in related structures (Adam et al., 1997; Chen et al., 2014, 2015). Within the same ligand, the dihedral angles formed by the benzene rings are (9) and (9). The molecular structure is stabilized by weak C HO hydrogen bonds (Table 1). The crystal packing is mainly stabilized by van der Waals forces. 1of2

2 Table 1 Hydrogen-bond geometry (Å, ). D HA D H HA DA D HA C8 H8CO (4) 123 C9 H9CO (4) 123 C33 H33AO (4) 123 C34 H34AO (4) 124 Table 2 Experimental details. Figure 1 The molecular structure of the title compound, with the atom labelling and 30% probability displacement ellipsoids. Synthesis and crystallization To a solution of the Schiff base (1 mmol) in 10 ml methanol was added a solution of Co(AcO) 2 H 2 O (0.5 mmol) in 10 ml ethanol. The resulting mixture was refluxed for 4 6 h and then cooled to room temperature. The precipitate obtained was filtered, washed in ice-cold ethanol and dried in vacuo. X-ray quality crystals were grown by layering a CHCl 3 solution (3 ml) of the compound with CH 3 CN (5 ml). Refinement Crystal data, data collection and structure refinement details are summarized in Table 2. The methyl C atoms of the tertbutyl groups are rotationally disordered, with site occupancies of (3) and (9) for the major components (C12, C13, C14 and C37A, C38A, C39A), and (3) and (9) for the minor components (C12A, C13A, C14A and C37, C38, C39). The C C bond lengths involving the disordered atoms were restrained to 1.50 (1) Å. SIMU, SADI and DELU restraints were also applied. The structure contains a solventaccessible void which was treated using the SQUEEZE routine from PLATON (Spek, 2015). Acknowledgements The authors acknowledge the SAIF, IIT, Madras, for the data collection. Crystal data Chemical formula [Co(C 25 H 35 N 2 O) 2 ] M r Crystal system, space group Triclinic, P1 Temperature (K) 295 a, b, c (Å) (1), (2), (2),, ( ) (1), (1), (2) V (Å 3 ) (6) Z 2 Radiation type Mo K (mm 1 ) 0.38 Crystal size (mm) Data collection Diffractometer Bruker Kappa APEXII CCD Absorption correction Multi-scan (SADABS; Bruker, 2004) T min, T max 0.851, No. of measured, independent and 38553, 8091, 5894 observed [I > 2(I)] reflections R int (sin /) max (Å 1 ) Refinement R[F 2 >2(F 2 )], wr(f 2 ), S 0.049, 0.146, 1.12 No. of reflections 8091 No. of parameters 592 No. of restraints 105 H-atom treatment H-atom parameters constrained max, min (e Å 3 ) 0.43, 0.36 Computer programs: APEX2 and SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL2016 (Sheldrick, 2015) and PLATON (Spek, 2009). References Adam, K. R., Anderson, P. A., Astley, T., Atkinson, I. M., Charnock, J. M., Garner, C. D., Gulbis, J. M., Hambley, T. W., Hitchman, M. A., Keene, F. R. & Tiekink, E. R. T. (1997). J. Chem. Soc. Dalton Trans. pp Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Chen, Y. M., Gao, Q., Chen, W. Q., Gao, D. D., Li, Y. H., Liu, W. & Li, W. (2015). Chem. Asian J. 10, Chen, Y. M., Gao, Q., Zhang, H. F., Gao, D. D., Li, Y. H., Liu, W. & Li, W. (2014). Polyhedron, 71, Nair, B., Shah, A., Baluja, S. & Chanda, S. (2006). J. Serb. Chem. Soc. 71, Sheldrick, G. M. (2008). Acta Cryst. A64, Sheldrick, G. M. (2015). Acta Cryst. A71, 3 8. Spek, A. L. (2009). Acta Cryst. D65, Spek, A. L. (2015). Acta Cryst. C71, of2 Rani et al. [Co(C 25 H 35 N 2 O) 2 ]

3 full crystallographic data [ Bis(4,6-di-tert-butyl-2-{N-[4-(diethylamino)phenyl]carboximidoyl}- phenolato)cobalt(ii) C.Vidya Rani, L. Mitu, G. Chakkaravarthi and G. Rajagopal Bis(4,6-di-tert-butyl-2-{N-[4-(diethylamino)phenyl]carboximidoyl}phenolato)cobalt(II) Crystal data [Co(C 25 H 35 N 2 O) 2 ] M r = Triclinic, P1 a = (1) Å b = (2) Å c = (2) Å α = (1) β = (1) γ = (2) V = (6) Å 3 Data collection Bruker Kappa APEXII CCD diffractometer ω and φ scan Absorption correction: multi-scan (SADABS; Bruker, 2004) T min = 0.851, T max = measured reflections Refinement Refinement on F 2 Least-squares matrix: full R[F 2 > 2σ(F 2 )] = wr(f 2 ) = S = reflections 592 parameters 105 restraints Z = 2 F(000) = 882 D x = Mg m 3 Mo Kα radiation, λ = Å Cell parameters from 8860 reflections θ = µ = 0.38 mm 1 T = 295 K Block, colourless mm 8091 independent reflections 5894 reflections with I > 2σ(I) R int = θ max = 24.3, θ min = 2.0 h = k = l = Hydrogen site location: inferred from neighbouring sites H-atom parameters constrained w = 1/[σ 2 (F o2 ) + (0.0808P) P] where P = (F o 2 + 2F c2 )/3 (Δ/σ) max < Δρ max = 0.43 e Å 3 Δρ min = 0.36 e Å 3 Special details 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. All H atoms were positioned geometrically and refined as riding, with C H = Å, and U iso (H) = 1.2 U eq (C) or 1.5 U eq (C) for methyl H atoms. A rotating model was used for the methyl groups. data-1

4 Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 ) x y z U iso */U eq Occ. (<1) C (2) (2) (15) (6) C (2) (2) (16) (7) C (2) (2) (18) (7) H * C (2) (2) (18) (7) C (2) (2) (17) (7) H * C (2) (2) (15) (6) C (3) (2) (18) (8) C (3) (3) (2) (11) H8A * H8B * H8C * C (3) (3) (2) (11) H9A * H9B * H9C * C (4) (3) (2) (15) H10A * H10B * H10C * C (3) (2) (19) (7) C (4) (4) (3) (9) (3) H12A * (3) H12B * (3) H12C * (3) C (4) (3) (3) (9) (3) H13A * (3) H13B * (3) H13C * (3) C (4) (3) (2) (9) (3) H14A * (3) H14B * (3) H14C * (3) C12A (16) (13) (11) (11) (3) H12D * (3) H12E * (3) H12F * (3) C13A (10) (15) (11) (11) (3) H13D * (3) H13E * (3) H13F * (3) C14A (15) (12) (10) (13) (3) H14D * (3) H14E * (3) data-2

5 H14F * (3) C (2) (2) (15) (6) H * C (2) (2) (16) (6) C (2) (2) (17) (7) H * C (2) (2) (18) (8) H * C (3) (2) (2) (9) C (3) (2) (2) (11) H * C (3) (2) (19) (9) H * C (4) (3) (3) (13) H22A * H22B * C (5) (5) (3) (2) H23A * H23B * H23C * C (6) (3) (3) (19) H24A * H24B * C (6) (4) (4) (3) H25A * H25B * H25C * C (3) (2) (17) (7) C (3) (2) (18) (8) C (4) (3) (2) (10) H * C (3) (3) (2) (10) C (3) (3) (19) (9) H * C (3) (2) (17) (8) C (3) (3) (2) (9) C (3) (3) (2) (11) H33A * H33B * H33C * C (4) (3) (3) (14) H34A * H34B * H34C * C (4) (4) (3) (15) H35A * H35B * H35C * data-3

6 C (4) (3) (2) (11) C (10) (2) (14) (2) (9) H37A * (9) H37B * (9) H37C * (9) C (13) (8) (10) (16) (9) H38A * (9) H38B * (9) H38C * (9) C (8) (12) (7) (16) (9) H39A * (9) H39B * (9) H39C * (9) C37A (10) (17) (12) (2) (9) H37D * (9) H37E * (9) H37F * (9) C38A (11) (8) (8) (18) (9) H38D * (9) H38E * (9) H38F * (9) C39A (8) (10) (7) (15) (9) H39D * (9) H39E * (9) H39F * (9) C (3) (2) (17) (8) H * C (2) (2) (16) (7) C (2) (2) (18) (7) H * C (2) (3) (18) (8) H * C (2) (3) (17) (8) C (3) (2) (19) (8) H * C (2) (2) (18) (8) H * C (3) (3) (3) (12) H47A * H47B * C (3) (4) (3) (2) H48A * H48B * H48C * C (3) (3) (2) (10) H49A * H49B * C (4) (3) (3) (13) data-4

7 H50A * H50B * H50C * N (17) (16) (12) (5) N (19) (18) (13) (6) N (3) (2) (19) (10) N (2) (2) (19) (8) O (17) (15) (12) (5) O (15) (14) (11) (5) CO (3) (3) (2) (16) Atomic displacement parameters (Å 2 ) U 11 U 22 U 33 U 12 U 13 U 23 C (14) (15) (15) (12) (12) (13) C (16) (16) (16) (13) (13) (14) C (18) (16) (19) (13) (14) (14) C (17) (17) (18) (13) (14) (15) C (17) (16) (15) (13) (13) (13) C (14) (15) (15) (11) (11) (13) C (2) (18) (18) (16) (16) (15) C (3) (3) (2) (2) (2) (2) C (3) (3) (2) (2) (18) (2) C (4) (2) (2) (2) (2) (19) C (17) (16) (15) (12) (14) (14) C (17) (2) (19) (14) (16) (17) C (2) (17) (19) (14) (17) (15) C (2) (19) (15) (16) (15) (14) C12A (2) (2) (2) (17) (17) (19) C13A (2) (2) (2) (17) (17) (18) C14A (2) (2) (2) (17) (19) (19) C (14) (16) (14) (12) (11) (13) C (16) (15) (15) (12) (13) (13) C (16) (17) (18) (13) (14) (15) C (18) (2) (18) (15) (14) (16) C (2) (19) (2) (16) (18) (16) C (3) (18) (2) (19) (2) (18) C (2) (19) (19) (17) (17) (16) C (3) (3) (2) (2) (19) (2) C (5) (5) (3) (4) (3) (3) C (6) (3) (4) (3) (4) (2) C (7) (4) (6) (4) (5) (4) C (2) (15) (16) (14) (15) (13) C (2) (17) (17) (15) (16) (15) C (3) (2) (2) (19) (2) (17) C (3) (2) (19) (2) (19) (18) C (2) (2) (2) (19) (18) (19) C (2) (18) (17) (15) (15) (15) data-5

8 C (3) (2) (2) (18) (19) (19) C (3) (3) (3) (2) (2) (2) C (4) (3) (3) (3) (3) (3) C (3) (4) (4) (3) (3) (3) C (3) (2) (18) (2) (2) (18) C (4) (5) (5) (6) (6) (3) C (4) (3) (3) (3) (3) (3) C (3) (3) (4) (3) (3) (3) C37A (5) (5) (4) (6) (6) (2) C38A (4) (3) (3) (3) (4) (3) C39A (3) (3) (3) (3) (3) (3) C (19) (19) (17) (15) (14) (16) C (17) (17) (15) (14) (13) (14) C (17) (2) (19) (15) (14) (17) C (19) (2) (19) (16) (15) (17) C (19) (2) (18) (16) (14) (16) C (17) (2) (2) (15) (15) (18) C (19) (18) (2) (15) (15) (16) C (18) (3) (3) (2) (2) (3) C (3) (4) (5) (3) (3) (4) C (2) (3) (2) (2) (2) (19) C (3) (3) (3) (3) (3) (2) N (12) (12) (12) (10) (10) (11) N (14) (14) (13) (11) (11) (12) N (3) (17) (19) (17) (16) (16) N (14) (2) (2) (14) (14) (18) O (13) (13) (12) (10) (10) (10) O (11) (11) (10) (9) (9) (9) CO (3) (3) (2) (17) (17) (19) Geometric parameters (Å, º) C1 O (3) C26 C (4) C1 C (3) C27 C (4) C1 C (3) C27 C (5) C2 C (4) C28 C (5) C2 C (4) C28 H C3 C (4) C29 C (4) C3 H C29 C (5) C4 C (4) C30 C (4) C4 C (4) C30 H C5 C (3) C31 C (4) C5 H C32 C (5) C6 C (3) C32 C (4) C7 C (4) C32 C (5) C7 C (4) C33 H33A C7 C (5) C33 H33B C8 H8A C33 H33C data-6

9 C8 H8B C34 H34A C8 H8C C34 H34B C9 H9A C34 H34C C9 H9B C35 H35A C9 H9C C35 H35B C10 H10A C35 H35C C10 H10B C36 C (7) C10 H10C C36 C (6) C11 C (4) C36 C37A (12) C11 C13A (8) C36 C (8) C11 C (4) C36 C39A (10) C11 C12A (8) C36 C38A (11) C11 C (4) C37 H37A C11 C14A (8) C37 H37B C12 H12A C37 H37C C12 H12B C38 H38A C12 H12C C38 H38B C13 H13A C38 H38C C13 H13B C39 H39A C13 H13C C39 H39B C14 H14A C39 H39C C14 H14B C37A H37D C14 H14C C37A H37E C12A H12D C37A H37F C12A H12E C38A H38D C12A H12F C38A H38E C13A H13D C38A H38F C13A H13E C39A H39D C13A H13F C39A H39E C14A H14D C39A H39F C14A H14E C40 N (3) C14A H14F C40 H C15 N (3) C41 C (4) C15 H C41 C (4) C16 C (4) C41 N (3) C16 C (4) C42 C (4) C16 N (3) C42 H C17 C (4) C43 C (4) C17 H C43 H C18 C (4) C44 N (4) C18 H C44 C (4) C19 N (4) C45 C (4) C19 C (4) C45 H C20 C (4) C46 H C20 H C47 N (4) C21 H C47 C (5) C22 N (5) C47 H47A C22 C (7) C47 H47B data-7

10 C22 H22A C48 H48A C22 H22B C48 H48B C23 H23A C48 H48C C23 H23B C49 N (4) C23 H23C C49 C (5) C24 N (5) C49 H49A C24 C (7) C49 H49B C24 H24A C50 H50A C24 H24B C50 H50B C25 H25A C50 H50C C25 H25B N1 CO (2) C25 H25C N2 CO (2) C26 O (3) O1 CO (18) C26 C (4) O2 CO (17) O2 C1 C (2) C30 C29 C (4) O2 C1 C (2) C28 C29 C (3) C6 C1 C (2) C29 C30 C (3) C3 C2 C (2) C29 C30 H C3 C2 C (2) C31 C30 H C1 C2 C (2) C26 C31 C (3) C2 C3 C (3) C26 C31 C (2) C2 C3 H C30 C31 C (3) C4 C3 H C34 C32 C (3) C5 C4 C (2) C34 C32 C (3) C5 C4 C (3) C33 C32 C (3) C3 C4 C (3) C34 C32 C (3) C4 C5 C (2) C33 C32 C (3) C4 C5 H C27 C32 C (3) C6 C5 H C32 C33 H33A C5 C6 C (2) C32 C33 H33B C5 C6 C (2) H33A C33 H33B C1 C6 C (2) C32 C33 H33C C9 C7 C (2) H33A C33 H33C C9 C7 C (3) H33B C33 H33C C2 C7 C (2) C32 C34 H34A C9 C7 C (3) C32 C34 H34B C2 C7 C (3) H34A C34 H34B C10 C7 C (3) C32 C34 H34C C7 C8 H8A H34A C34 H34C C7 C8 H8B H34B C34 H34C H8A C8 H8B C32 C35 H35A C7 C8 H8C C32 C35 H35B H8A C8 H8C H35A C35 H35B H8B C8 H8C C32 C35 H35C C7 C9 H9A H35A C35 H35C C7 C9 H9B H35B C35 H35C H9A C9 H9B C38 C36 C (7) data-8

11 C7 C9 H9C C38 C36 C (6) H9A C9 H9C C39 C36 C (5) H9B C9 H9C C37A C36 C (12) C7 C10 H10A C38 C36 C (14) C7 C10 H10B C39 C36 C (6) H10A C10 H10B C29 C36 C (14) C7 C10 H10C C37A C36 C39A (8) H10A C10 H10C C29 C36 C39A (4) H10B C10 H10C C37A C36 C38A (10) C14 C11 C (3) C29 C36 C38A (5) C13A C11 C12A (11) C39A C36 C38A (6) C14 C11 C (3) C36 C37 H37A C12 C11 C (3) C36 C37 H37B C14 C11 C (3) H37A C37 H37B C13A C11 C (6) C36 C37 H37C C12 C11 C (3) H37A C37 H37C C12A C11 C (7) H37B C37 H37C C13 C11 C (3) C36 C38 H38A C13A C11 C14A (10) C36 C38 H38B C12A C11 C14A 98.0 (11) H38A C38 H38B C4 C11 C14A (7) C36 C38 H38C C11 C12 H12A H38A C38 H38C C11 C12 H12B H38B C38 H38C H12A C12 H12B C36 C39 H39A C11 C12 H12C C36 C39 H39B H12A C12 H12C H39A C39 H39B H12B C12 H12C C36 C39 H39C C11 C13 H13A H39A C39 H39C C11 C13 H13B H39B C39 H39C H13A C13 H13B C36 C37A H37D C11 C13 H13C C36 C37A H37E H13A C13 H13C H37D C37A H37E H13B C13 H13C C36 C37A H37F C11 C14 H14A H37D C37A H37F C11 C14 H14B H37E C37A H37F H14A C14 H14B C36 C38A H38D C11 C14 H14C C36 C38A H38E H14A C14 H14C H38D C38A H38E H14B C14 H14C C36 C38A H38F C11 C12A H12D H38D C38A H38F C11 C12A H12E H38E C38A H38F H12D C12A H12E C36 C39A H39D C11 C12A H12F C36 C39A H39E H12D C12A H12F H39D C39A H39E H12E C12A H12F C36 C39A H39F C11 C13A H13D H39D C39A H39F C11 C13A H13E H39E C39A H39F H13D C13A H13E N2 C40 C (3) data-9

12 C11 C13A H13F N2 C40 H H13D C13A H13F C31 C40 H H13E C13A H13F C46 C41 C (3) C11 C14A H14D C46 C41 N (2) C11 C14A H14E C42 C41 N (2) H14D C14A H14E C43 C42 C (3) C11 C14A H14F C43 C42 H H14D C14A H14F C41 C42 H H14E C14A H14F C42 C43 C (3) N1 C15 C (2) C42 C43 H N1 C15 H C44 C43 H C6 C15 H N4 C44 C (3) C17 C16 C (3) N4 C44 C (3) C17 C16 N (2) C43 C44 C (3) C21 C16 N (2) C46 C45 C (3) C16 C17 C (3) C46 C45 H C16 C17 H C44 C45 H C18 C17 H C45 C46 C (3) C17 C18 C (3) C45 C46 H C17 C18 H C41 C46 H C19 C18 H N4 C47 C (3) N3 C19 C (3) N4 C47 H47A N3 C19 C (3) C48 C47 H47A C18 C19 C (3) N4 C47 H47B C21 C20 C (3) C48 C47 H47B C21 C20 H H47A C47 H47B C19 C20 H C47 C48 H48A C20 C21 C (3) C47 C48 H48B C20 C21 H H48A C48 H48B C16 C21 H C47 C48 H48C N3 C22 C (4) H48A C48 H48C N3 C22 H22A H48B C48 H48C C23 C22 H22A N4 C49 C (3) N3 C22 H22B N4 C49 H49A C23 C22 H22B C50 C49 H49A H22A C22 H22B N4 C49 H49B C22 C23 H23A C50 C49 H49B C22 C23 H23B H49A C49 H49B H23A C23 H23B C49 C50 H50A C22 C23 H23C C49 C50 H50B H23A C23 H23C H50A C50 H50B H23B C23 H23C C49 C50 H50C N3 C24 C (4) H50A C50 H50C N3 C24 H24A H50B C50 H50C C25 C24 H24A C15 N1 C (2) N3 C24 H24B C15 N1 CO (17) C25 C24 H24B C16 N1 CO (15) H24A C24 H24B C40 N2 C (2) data-10

13 C24 C25 H25A C40 N2 CO (2) C24 C25 H25B C41 N2 CO (16) H25A C25 H25B C19 N3 C (3) C24 C25 H25C C19 N3 C (3) H25A C25 H25C C22 N3 C (3) H25B C25 H25C C44 N4 C (3) O1 C26 C (3) C44 N4 C (3) O1 C26 C (3) C47 N4 C (3) C31 C26 C (3) C26 O1 CO (19) C28 C27 C (3) C1 O2 CO (16) C28 C27 C (3) O1 CO1 O (8) C26 C27 C (3) O1 CO1 N (8) C27 C28 C (3) O2 CO1 N (8) C27 C28 H O1 CO1 N (8) C29 C28 H O2 CO1 N (8) C30 C29 C (3) N2 CO1 N (9) O2 C1 C2 C (2) C26 C27 C32 C (4) C6 C1 C2 C3 1.1 (4) C28 C27 C32 C (4) O2 C1 C2 C7 0.7 (4) C26 C27 C32 C (3) C6 C1 C2 C (2) C30 C29 C36 C (8) C1 C2 C3 C4 0.0 (4) C28 C29 C36 C (9) C7 C2 C3 C (3) C30 C29 C36 C (8) C2 C3 C4 C5 1.1 (4) C28 C29 C36 C (7) C2 C3 C4 C (3) C30 C29 C36 C37A (7) C3 C4 C5 C6 1.0 (4) C28 C29 C36 C37A 72.3 (8) C11 C4 C5 C (3) C30 C29 C36 C (8) C4 C5 C6 C1 0.2 (4) C28 C29 C36 C (9) C4 C5 C6 C (2) C30 C29 C36 C39A 31.2 (7) O2 C1 C6 C (2) C28 C29 C36 C39A (6) C2 C1 C6 C5 1.2 (3) C30 C29 C36 C38A (6) O2 C1 C6 C (4) C28 C29 C36 C38A 42.6 (6) C2 C1 C6 C (2) C26 C31 C40 N2 2.7 (5) C3 C2 C7 C (3) C30 C31 C40 N (3) C1 C2 C7 C (3) C46 C41 C42 C (4) C3 C2 C7 C (4) N2 C41 C42 C (3) C1 C2 C7 C (3) C41 C42 C43 C (5) C3 C2 C7 C (3) C42 C43 C44 N (3) C1 C2 C7 C (3) C42 C43 C44 C (4) C5 C4 C11 C (4) N4 C44 C45 C (3) C3 C4 C11 C (3) C43 C44 C45 C (4) C5 C4 C11 C13A 66.3 (9) C44 C45 C46 C (5) C3 C4 C11 C13A (8) C42 C41 C46 C (4) C5 C4 C11 C (3) N2 C41 C46 C (3) C3 C4 C11 C (4) C6 C15 N1 C (2) C5 C4 C11 C12A 55.4 (9) C6 C15 N1 CO1 4.9 (3) C3 C4 C11 C12A (9) C17 C16 N1 C (3) C5 C4 C11 C (3) C21 C16 N1 C (3) data-11

14 C3 C4 C11 C (4) C17 C16 N1 CO (2) C5 C4 C11 C14A (10) C21 C16 N1 CO (3) C3 C4 C11 C14A 20.2 (10) C31 C40 N2 C (3) C5 C6 C15 N (2) C31 C40 N2 CO1 3.4 (4) C1 C6 C15 N1 2.2 (4) C46 C41 N2 C (4) C21 C16 C17 C (4) C42 C41 N2 C (3) N1 C16 C17 C (2) C46 C41 N2 CO (2) C16 C17 C18 C (5) C42 C41 N2 CO (3) C17 C18 C19 N (3) C18 C19 N3 C (6) C17 C18 C19 C (5) C20 C19 N3 C (4) N3 C19 C20 C (4) C18 C19 N3 C (4) C18 C19 C20 C (5) C20 C19 N3 C (6) C19 C20 C21 C (6) C23 C22 N3 C (5) C17 C16 C21 C (5) C23 C22 N3 C (5) N1 C16 C21 C (3) C25 C24 N3 C (5) O1 C26 C27 C (3) C25 C24 N3 C (5) C31 C26 C27 C (4) C43 C44 N4 C (3) O1 C26 C27 C (4) C45 C44 N4 C (5) C31 C26 C27 C (3) C43 C44 N4 C (5) C26 C27 C28 C (5) C45 C44 N4 C (3) C32 C27 C28 C (3) C48 C47 N4 C (4) C27 C28 C29 C (5) C48 C47 N4 C (4) C27 C28 C29 C (3) C50 C49 N4 C (4) C28 C29 C30 C (5) C50 C49 N4 C (4) C36 C29 C30 C (3) C31 C26 O1 CO (4) O1 C26 C31 C (3) C27 C26 O1 CO (19) C27 C26 C31 C (4) C6 C1 O2 CO1 1.0 (3) O1 C26 C31 C (4) C2 C1 O2 CO (16) C27 C26 C31 C (3) C26 O1 CO1 O (2) C29 C30 C31 C (5) C26 O1 CO1 N (2) C29 C30 C31 C (3) C26 O1 CO1 N (2) C28 C27 C32 C (3) C1 O2 CO1 O (2) C26 C27 C32 C (4) C1 O2 CO1 N (2) C28 C27 C32 C (3) C1 O2 CO1 N1 1.2 (2) Hydrogen-bond geometry (Å, º) D H A D H H A D A D H A C8 H8C O (4) 123 C9 H9C O (4) 123 C33 H33A O (4) 123 C34 H34A O (4) 124 data-12