data reports 1-(Pyridin-2-yl)-2,4-bis[(pyridin-2-yl)carbonyl]- 3,5-bis(3,4,5-trimethoxyphenyl)cyclohexanol 2.25-hydrate Structure description

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1 ISSN (Pyridin-2-yl)-2,4-bis[(pyridin-2-yl)carbonyl]- 3,5-bis(3,4,5-trimethoxyphenyl)cyclohexanol 2.25-hydrate Era Dravida Thendral, a S. Gomathi, b U. Mohamooda Sumaya, c K. Biruntha c and G. Usha a * Received 28 October 2017 Accepted 10 November 2017 a PG and Research Department of Physics, Queen Mary s College, Chennai-4, Tamilnadu, India, b PG Department of Physics, Bhaktavatsalam Memorial College for Women, Chennai-80, Tamilnadu, India, and c Department of Physics, Bharathi Women s College, Chennai-108, Tamilnadu, India. *Correspondence guqmc@yahoo.com Edited by P. C. Healy, Griffith University, Australia Keywords: cyclohexanol; conformation; molecular interactions; trifurcated; crystal structure. CCDC reference: Structural data: full structural data are available from iucrdata.iucr.org In the title compound, C 41 H 41 N 3 O H 2 O, the cyclohexanol ring adopts a chair conformation. The cyclohexanol ring makes dihedral angles of (7) and (8) with the mean planes of the trimethoxyphenyl rings and dihedral angles of (8), (7) and (8) with the pyridine rings. In the crystal, the packing is stabilized by C HO, O HO and O HN hydrogen bonds involving water molecules and methoxy O atoms, resulting in a supramolecular network. One of the methoxy groups is disordered over two sets of sites with occupancy factors of 0.63 (3) and 0.37 (3). Structure description The title compound (Fig. 1) has a central cyclohexanol ring attached to two trimethoxyphenyl, one pyridine and two pyridinecarbonyl rings. The dihedral angle between the trimethoxyphenyl rings E and F is (7). The cyclohexanol ring A (C39 C44) makes dihedral angles of (8) and (7), respectively, with the mean planes of the rings E (C10 C15) and F (C1 C6). The pyridine rings B (N2/C20 C24), C (N1/C25 C29) and D (N1/C25 C29) are inclined to the central cyclohexanol ring by dihedral angles of (7), (8) and (8), respectively. The cyclohexanol ring A adopts a chair conformation with puckering parameters q 2 = (2), q 3 = (2) and Q T = (2) Å, 2 = 288 (4) and 2 = 3.81 (19), and is similar to that observed in reported structures (Çelik et al., 2016; Fun et al., 2012). In the crystal, the molecules are linked by C HO, O HOandO HN hydrogen bonds (Fig. 2, Table 1). The trifurcated atom O10 (acting as donor to two 1of3

2 Table 1 Hydrogen-bond geometry (Å, ). D HA D H HA DA D HA C8 H8BO (5) 114 C9 H9BO7 i (4) 168 C11 H11O8 ii (3) 163 C16 H16BO (15) 139 C24 H24O12 iii (15) 125 C27 H27O4 iv (4) 143 C44 H44O11 v (4) 153 O9 H9O7 ii (2) 139 O9 H9O (2) 129 O11 H11BN (2) 2.02 (2) (4) 169 (3) O11 H11AO10 vi 0.87 (2) 1.91 (2) (4) 171 (3) O10 H10AN (2) 2.00 (2) (4) 175 (4) O10 H10BO1 vi 0.86 (2) 2.16 (3) (3) 151 (5) Symmetry codes: (i) x þ 3 2 ; y þ 1 2 ; z þ 3 2 ; (ii) x þ 1; y; z þ 1; (iii) x þ 1 2 ; y þ 1 2 ; z þ 3 2 ; (iv) x 1 2 ; y 1 2 ; z 1 2 ; (v) x þ 1 2 ; y 1 2 ; z þ 3 2 ; (vi) x þ 1; y; z þ 2. Table 2 Experimental details. Crystal data Chemical formula 4C 41 H 41 N 3 O 9 9H 2 O M r Crystal system, space group Monoclinic, P2 1 /n Temperature (K) 293 a, b, c (Å) (10), (7), (9) ( ) (2) V (Å 3 ) (4) Z 1 Radiation type Mo K (mm 1 ) 0.09 Crystal size (mm) Data collection Diffractometer Bruker Kappa APEXII CCD Absorption correction Multi-scan (SADABS; Bruker, 2004) T min, T max 0.972, No. of measured, independent and 38138, 6999, 4142 observed [I > 2(I)] reflections R int (sin /) max (Å 1 ) Refinement R[F 2 >2(F 2 )], wr(f 2 ), S 0.047, 0.130, 1.08 No. of reflections 6995 No. of parameters 533 No. of restraints 13 H-atom treatment H atoms treated by a mixture of independent and constrained refinement max, min (e Å 3 ) 0.18, 0.20 Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SIR92 (Altomare et al., 1993), SHELXL2014 (Sheldrick, 2015), ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008). Figure 1 An ORTEP plot of the title compound with displacement ellipsoids drawn at the 20% probability level. Figure 2 Linking of the molecules and water molecules by hydrogen bonds (dashed lines). Figure 3 The crystal packing of the title compound, viewed along the a axis. Dashed lines indicate hydrogen bonds. 2of3 Dravida Thendral et al. 4C 41 H 41 N 3 O 9 9H 2 O

3 hydrogen bonds and acceptor to one) and bifurcated atom O11 (acting as acceptor to two hydrogen bonds) of the water molecules are actively involved in the formation of hydrogen bonds through carbonyl O and pyridine N atoms. The O9 atom from the hydroxyl group generates intra- and intermolecular interactions with ketone atoms through O9 H9O8 and O9 H9O7 bonds. The packing of the molecules viewed along the a axis is shown in Fig. 3. Synthesis and crystallization The title compound was synthesized by the following Claisen Schmidt reaction. In this procedure, 4-acetylpyridine(1.5 ml, 0.01 mol) and 3,4,5-trimethoxybenzaldehyde (2.6 g, 0.01 mol) were dissolved in 50 ml of ethanol in a round-bottomed flask. After 15 minutes, NaOH (10%) was added and the reaction mixture was maintained at 283 K and stirred for 5 h. Then the mixture was poured onto ice. The white-coloured precipitate was collected and washed with distilled water. A colourless, diffraction-quality crystal was obtained from repeated recrystallization from ethanol solution (yield: 87%, m.p. 398 K). Refinement Crystal data, data collection and structure refinement details are summarized in Table 2. Atom C7 and its attached H atoms are disordered over two sets of sites with occupancy factors of 0.63 (3) and 0.37 (3). Atom O12 was refined with a fixed occupancy factor of 0.25 and no H atoms attached. Acknowledgements The authors thank the Central Instrumentation Facility (DST FIST), Queen Mary s College, Chennai-4, for computing facilities and SAIF, IIT, Madras, for the X-ray data collection facilities. References Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Çelik, Í., Ersanlı, C. C., Akkurt, M., Gezegen, H. & Köseoğlu, R. (2016). Acta Cryst. E72, Farrugia, L. J. (2012). J. Appl. Cryst. 45, Fun, H.-K., Ooi, C. W., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2012). Acta Cryst. E68, o1633 o1634. Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, Sheldrick, G. M. (2015). Acta Cryst. C71, 3 8. Dravida Thendral et al. 4C 41 H 41 N 3 O 9 9H 2 O 3of3

4 full crystallographic data [ 1-(Pyridin-2-yl)-2,4-bis[(pyridin-2-yl)carbonyl]-3,5-bis(3,4,5-trimethoxyphenyl)- cyclohexanol 2.25-hydrate Era Dravida Thendral, S. Gomathi, U. Mohamooda Sumaya, K. Biruntha and G. Usha 1-(Pyridin-2-yl)-2,4-bis[(pyridin-2-yl)carbonyl]-3,5-bis(3,4,5-trimethoxyphenyl)-cyclohexanol 2.25-hydrate Crystal data 4C 41 H 41 N 3 O 9 9H 2 O M r = Monoclinic, P2 1 /n a = (10) Å b = (7) Å c = (9) Å β = (2) V = (4) Å 3 Z = 1 Data collection Bruker Kappa APEXII CCD diffractometer Radiation source: fine-focus sealed tube Graphite monochromator ω and φ scan Absorption correction: multi-scan (SADABS; Bruker, 2004) T min = 0.972, T max = Refinement Refinement on F 2 Least-squares matrix: full R[F 2 > 2σ(F 2 )] = wr(f 2 ) = S = reflections 533 parameters 13 restraints F(000) = 1608 D x = Mg m 3 Mo Kα radiation, λ = Å Cell parameters from 7551 reflections θ = µ = 0.09 mm 1 T = 293 K Block, colourless mm measured reflections 6999 independent reflections 4142 reflections with I > 2σ(I) R int = θ max = 25.0, θ min = 2.2 h = k = l = Hydrogen site location: mixed H atoms treated by a mixture of independent and constrained refinement w = 1/[σ 2 (F o2 ) + (0.0408P) P] where P = (F o 2 + 2F c2 )/3 (Δ/σ) max < Δρ max = 0.18 e Å 3 Δρ min = 0.20 e Å 3 Special details Refinement. H atoms were positioned geometrically and treated as riding on their parent atoms and refined with, C H = Å and O H = 0.82 Å, with U iso (H) = 1.5 U eq (c-methyl) and U iso (H) = 1.2Ueq(O) for other H atoms. The water H atoms were identified through Fourier maps and fixed with their parent O atoms using DFIX 0.82 (2). data-1

5 Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 ) x y z U iso */U eq Occ. (<1) C (16) (14) (13) (5) C (18) (16) (13) (6) H * C (2) (18) (14) (7) C (2) (18) (15) (7) C (2) (17) (16) (7) C (18) (16) (14) (6) H * C (2) (2) (13) (7) 0.37 (3) H7A * 0.37 (3) H7B * 0.37 (3) H7C * 0.37 (3) C (13) (6) (10) (4) 0.63 (3) H * 0.63 (3) H * 0.63 (3) H * 0.63 (3) C (4) (3) (3) (18) H8A * H8B * H8C * C (3) (3) (2) (12) H9A * H9B * H9C * C (18) (15) (13) (6) C (19) (16) (14) (6) H * C (2) (17) (15) (7) C (2) (16) (14) (7) C (2) (17) (14) (7) C (19) (16) (14) (6) H * C (3) (3) (3) (18) H16A * H16B * H16C * C (3) (2) (2) (13) H17A * H17B * H17C * C (2) (2) (2) (10) H18A * H18B * H18C * C (17) (16) (13) (6) data-2

6 C (19) (16) (14) (7) C (3) (19) (18) (9) H * C (4) (2) (2) (14) H * N (3) (3) (19) (12) C (3) (3) (2) (11) H * C (2) (2) (16) (8) H * C (18) (15) (13) (6) C (2) (18) (14) (7) H * C (3) (2) (18) (10) H * N (19) (19) (16) (8) C (2) (2) (18) (8) H * C (18) (17) (15) (7) H * C (18) (15) (13) (6) C (17) (15) (13) (6) C (19) (18) (14) (7) H * C (2) (2) (16) (8) H * N (19) (17) (13) (7) C (2) (2) (17) (9) H * C (2) (18) (15) (8) H * C (16) (14) (12) (5) H * C (16) (14) (12) (5) H * C (16) (14) (12) (5) C (17) (15) (13) (6) H42A * H42B * C (16) (14) (12) (6) H * C (16) (14) (12) (5) H * O (17) (15) (12) (6) O (17) (15) (12) (7) O (17) (15) (13) (7) O (16) (12) (12) (6) O (15) (11) (11) (6) data-3

7 O (16) (13) (13) (6) O (12) (11) (9) (4) O (16) (11) (11) (6) O (11) (10) (8) (4) H * O (3) (2) (16) (10) O (2) (2) (18) (11) O (11) (10) (8) (5)* 0.25 H11B (3) (2) (11) (16)* H11A (2) (18) (14) (13)* H10A (3) (3) (15) 0.16 (2)* H10B (3) (3) (2) 0.16 (2)* Atomic displacement parameters (Å 2 ) U 11 U 22 U 33 U 12 U 13 U 23 C (14) (12) (13) (11) (11) (10) C (16) (14) (14) (12) (12) (11) C (18) (16) (15) (14) (13) (13) C (19) (17) (16) (15) (15) (14) C (18) (15) (17) (14) (15) (14) C (16) (14) (14) (12) (12) (12) C (14) (17) (10) (12) (10) (12) C (10) (6) (8) (5) (7) (5) C (5) (3) (4) (3) (4) (3) C (3) (3) (2) (2) (2) (2) C (16) (13) (13) (12) (11) (10) C (18) (14) (15) (12) (13) (11) C (18) (15) (16) (14) (14) (13) C (19) (14) (15) (13) (14) (12) C (19) (14) (15) (14) (13) (12) C (17) (14) (15) (12) (13) (12) C (4) (3) (5) (3) (4) (3) C (3) (18) (3) (18) (2) (19) C (2) (2) (3) (19) (2) (2) C (15) (14) (14) (11) (12) (11) C (18) (15) (15) (13) (13) (12) C (3) (17) (2) (17) (2) (16) C (4) (2) (3) (2) (3) (2) N (3) (3) (2) (2) (2) (2) C (3) (3) (3) (2) (2) (2) C (2) (2) (19) (16) (17) (16) C (16) (13) (13) (11) (12) (11) C (19) (18) (15) (14) (14) (13) C (3) (2) (18) (19) (18) (16) N (17) (2) (19) (15) (15) (15) C (19) (2) (2) (15) (16) (16) C (17) (16) (15) (13) (13) (13) data-4

8 C (16) (12) (13) (11) (12) (10) C (15) (13) (13) (11) (12) (11) C (18) (17) (15) (14) (13) (13) C (2) (2) (16) (16) (15) (15) N (19) (17) (14) (15) (13) (13) C (2) (2) (19) (18) (18) (17) C (19) (17) (16) (15) (14) (13) C (14) (12) (12) (10) (10) (10) C (14) (12) (12) (10) (11) (10) C (15) (13) (12) (11) (11) (10) C (16) (13) (12) (11) (11) (10) C (15) (12) (12) (11) (11) (10) C (14) (12) (12) (10) (11) (10) O (18) (15) (13) (13) (13) (12) O (19) (16) (14) (13) (13) (12) O (17) (15) (16) (13) (14) (13) O (16) (11) (15) (11) (13) (10) O (15) (10) (13) (10) (11) (9) O (15) (12) (16) (11) (13) (11) O (11) (11) (10) (9) (9) (8) O (17) (10) (12) (10) (12) (9) O (11) (9) (9) (8) (8) (7) O (3) (2) (18) (2) (19) (15) O (3) (3) (19) (2) (19) (2) Geometric parameters (Å, º) C1 C (3) C19 C (3) C1 C (3) C20 C (4) C1 C (3) C20 C (4) C2 C (3) C21 C (5) C2 H C21 H C3 C (4) C22 N (5) C3 O (3) C22 H C4 O (3) N2 C (5) C4 C (4) C23 C (4) C5 O (3) C23 H C5 C (3) C24 H C6 H C25 C (3) C7 O (11) C25 C (3) C7 H7A C25 C (3) C7 H7B C26 C (4) C7 H7C C26 H C7 O (7) C27 N (4) C7 H C27 H C7 H N1 C (4) C7 H C28 C (4) C8 O (4) C28 H data-5

9 C8 H8A C29 H C8 H8B C30 O (3) C8 H8C C30 C (3) C9 O (4) C30 C (3) C9 H9A C31 C (3) C9 H9B C31 C (3) C9 H9C C32 C (4) C10 C (3) C32 H C10 C (3) C33 N (4) C10 C (3) C33 H C11 C (3) N3 C (4) C11 H C34 C (4) C12 O (3) C34 H C12 C (4) C35 H C13 C (4) C39 C (3) C13 O (3) C39 C (3) C14 O (3) C39 H C14 C (3) C40 C (3) C15 H C40 H C16 O (4) C41 O (3) C16 H16A C41 C (3) C16 H16B C42 C (3) C16 H16C C42 H42A C17 O (3) C42 H42B C17 H17A C43 C (3) C17 H17B C43 H C17 H17C C44 H C18 O (4) O9 H C18 H18A O10 H10A (18) C18 H18B O10 H10B (19) C18 H18C O11 H11B (18) C19 O (3) O11 H11A (17) C19 C (3) C6 C1 C (2) C21 C22 H C6 C1 C (2) C23 N2 C (3) C2 C1 C (2) N2 C23 C (4) C3 C2 C (2) N2 C23 H C3 C2 H C24 C23 H C1 C2 H C20 C24 C (3) C4 C3 C (2) C20 C24 H C4 C3 O (2) C23 C24 H C2 C3 O (2) C26 C25 C (2) O2 C4 C (3) C26 C25 C (2) O2 C4 C (3) C29 C25 C (2) C3 C4 C (2) C25 C26 C (3) O3 C5 C (3) C25 C26 H O3 C5 C (2) C27 C26 H data-6

10 C6 C5 C (2) N1 C27 C (3) C1 C6 C (2) N1 C27 H C1 C6 H C26 C27 H C5 C6 H C28 N1 C (3) O1 C7 H7A N1 C28 C (3) O1 C7 H7B N1 C28 H H7A C7 H7B C29 C28 H O1 C7 H7C C28 C29 C (3) H7A C7 H7C C28 C29 H H7B C7 H7C C25 C29 H O1 C7 H O7 C30 C (2) O1 C7 H O7 C30 C (2) H7 1 C7 H C31 C30 C (2) O1 C7 H C32 C31 C (2) H7 1 C7 H C32 C31 C (2) H7 2 C7 H C35 C31 C (2) O2 C8 H8A C31 C32 C (3) O2 C8 H8B C31 C32 H H8A C8 H8B C33 C32 H O2 C8 H8C N3 C33 C (3) H8A C8 H8C N3 C33 H H8B C8 H8C C32 C33 H O3 C9 H9A C34 N3 C (2) O3 C9 H9B N3 C34 C (3) H9A C9 H9B N3 C34 H O3 C9 H9C C35 C34 H H9A C9 H9C C31 C35 C (3) H9B C9 H9C C31 C35 H C15 C10 C (2) C34 C35 H C15 C10 C (2) C1 C39 C (18) C11 C10 C (2) C1 C39 C (17) C12 C11 C (2) C40 C39 C (18) C12 C11 H C1 C39 H C10 C11 H C40 C39 H O6 C12 C (2) C44 C39 H O6 C12 C (3) C19 C40 C (18) C13 C12 C (3) C19 C40 C (18) C14 C13 O (3) C39 C40 C (18) C14 C13 C (2) C19 C40 H O5 C13 C (3) C39 C40 H O4 C14 C (2) C41 C40 H O4 C14 C (3) O9 C41 C (18) C13 C14 C (3) O9 C41 C (18) C10 C15 C (3) C25 C41 C (19) C10 C15 H O9 C41 C (18) C14 C15 H C25 C41 C (18) O4 C16 H16A C42 C41 C (17) O4 C16 H16B C41 C42 C (19) data-7

11 H16A C16 H16B C41 C42 H42A O4 C16 H16C C43 C42 H42A H16A C16 H16C C41 C42 H42B H16B C16 H16C C43 C42 H42B O5 C17 H17A H42A C42 H42B O5 C17 H17B C10 C43 C (19) H17A C17 H17B C10 C43 C (18) O5 C17 H17C C42 C43 C (18) H17A C17 H17C C10 C43 H H17B C17 H17C C42 C43 H O6 C18 H18A C44 C43 H O6 C18 H18B C30 C44 C (19) H18A C18 H18B C30 C44 C (18) O6 C18 H18C C43 C44 C (17) H18A C18 H18C C30 C44 H H18B C18 H18C C43 C44 H O8 C19 C (2) C39 C44 H O8 C19 C (2) C7 O1 C (8) C20 C19 C (2) C3 O1 C (4) C24 C20 C (3) C4 O2 C (3) C24 C20 C (2) C5 O3 C (2) C21 C20 C (3) C14 O4 C (2) C20 C21 C (4) C13 O5 C (2) C20 C21 H C12 O6 C (2) C22 C21 H C41 O9 H N2 C22 C (4) H10A O10 H10B 107 (3) N2 C22 H H11B O11 H11A 107 (2) C6 C1 C2 C3 1.4 (4) C30 C31 C35 C (3) C39 C1 C2 C (2) N3 C34 C35 C (5) C1 C2 C3 C4 0.6 (4) C6 C1 C39 C (2) C1 C2 C3 O (2) C2 C1 C39 C (3) C2 C3 C4 O (3) C6 C1 C39 C (2) O1 C3 C4 O2 3.4 (4) C2 C1 C39 C (3) C2 C3 C4 C5 3.0 (4) O8 C19 C40 C (3) O1 C3 C4 C (3) C20 C19 C40 C (3) O2 C4 C5 O3 2.3 (4) O8 C19 C40 C (3) C3 C4 C5 O (3) C20 C19 C40 C (2) O2 C4 C5 C (3) C1 C39 C40 C (2) C3 C4 C5 C6 3.5 (4) C44 C39 C40 C (18) C2 C1 C6 C5 0.9 (4) C1 C39 C40 C (18) C39 C1 C6 C (2) C44 C39 C40 C (2) O3 C5 C6 C (3) C26 C25 C41 O9 0.6 (3) C4 C5 C6 C1 1.6 (4) C29 C25 C41 O (2) C15 C10 C11 C (4) C26 C25 C41 C (2) C43 C10 C11 C (2) C29 C25 C41 C (3) C10 C11 C12 O (2) C26 C25 C41 C (2) C10 C11 C12 C (4) C29 C25 C41 C (3) data-8

12 O6 C12 C13 C (2) C19 C40 C41 O (2) C11 C12 C13 C (4) C39 C40 C41 O (2) O6 C12 C13 O5 3.8 (4) C19 C40 C41 C (2) C11 C12 C13 O (2) C39 C40 C41 C (18) O5 C13 C14 O4 3.9 (4) C19 C40 C41 C (2) C12 C13 C14 O (2) C39 C40 C41 C (2) O5 C13 C14 C (2) O9 C41 C42 C (2) C12 C13 C14 C (4) C25 C41 C42 C (19) C11 C10 C15 C (4) C40 C41 C42 C (3) C43 C10 C15 C (2) C15 C10 C43 C (3) O4 C14 C15 C (2) C11 C10 C43 C (2) C13 C14 C15 C (4) C15 C10 C43 C (3) O8 C19 C20 C (3) C11 C10 C43 C (2) C40 C19 C20 C (4) C41 C42 C43 C (19) O8 C19 C20 C (4) C41 C42 C43 C (2) C40 C19 C20 C (3) O7 C30 C44 C (3) C24 C20 C21 C (4) C31 C30 C44 C (2) C19 C20 C21 C (3) O7 C30 C44 C (3) C20 C21 C22 N2 2.8 (6) C31 C30 C44 C (2) C21 C22 N2 C (6) C10 C43 C44 C (3) C22 N2 C23 C (6) C42 C43 C44 C (18) C21 C20 C24 C (4) C10 C43 C44 C (2) C19 C20 C24 C (3) C42 C43 C44 C (2) N2 C23 C24 C (5) C1 C39 C44 C (2) C29 C25 C26 C (4) C40 C39 C44 C (18) C41 C25 C26 C (2) C1 C39 C44 C (19) C25 C26 C27 N1 0.4 (5) C40 C39 C44 C (2) C26 C27 N1 C (5) C4 C3 O1 C7 90 (2) C27 N1 C28 C (5) C2 C3 O1 C7 91 (2) N1 C28 C29 C (4) C4 C3 O1 C (10) C26 C25 C29 C (4) C2 C3 O1 C (10) C41 C25 C29 C (2) C3 C4 O2 C (3) O7 C30 C31 C (3) C5 C4 O2 C (4) C44 C30 C31 C (2) C6 C5 O3 C (4) O7 C30 C31 C (3) C4 C5 O3 C (3) C44 C30 C31 C (3) C13 C14 O4 C (3) C35 C31 C32 C (4) C15 C14 O4 C (4) C30 C31 C32 C (2) C14 C13 O5 C (3) C31 C32 C33 N3 0.2 (4) C12 C13 O5 C (3) C32 C33 N3 C (5) C13 C12 O6 C (3) C33 N3 C34 C (5) C11 C12 O6 C (4) C32 C31 C35 C (4) Hydrogen-bond geometry (Å, º) D H A D H H A D A D H A C8 H8B O (5) 114 C9 H9B O7 i (4) 168 data-9

13 C11 H11 O8 ii (3) 163 C16 H16B O (15) 139 C24 H24 O12 iii (15) 125 C27 H27 O4 iv (4) 143 C44 H44 O11 v (4) 153 O9 H9 O7 ii (2) 139 O9 H9 O (2) 129 O11 H11B N (2) 2.02 (2) (4) 169 (3) O11 H11A O10 vi 0.87 (2) 1.91 (2) (4) 171 (3) O10 H10A N (2) 2.00 (2) (4) 175 (4) O10 H10B O1 vi 0.86 (2) 2.16 (3) (3) 151 (5) Symmetry codes: (i) x+3/2, y+1/2, z+3/2; (ii) x+1, y, z+1; (iii) x+1/2, y+1/2, z+3/2; (iv) x 1/2, y 1/2, z 1/2; (v) x+1/2, y 1/2, z+3/2; (vi) x+1, y, z+2. data-10