Experimental. Crystal data. C 29 H 50 O 2 M r = Monoclinic, P2 1 a = (1) Å b = (2) Å c = (4) Å = 93.

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Hubert Sharp
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1 Acta Crystallographica Section E Structure Reports Online ISSN (5-Ethyl-6-methylheptan-2-yl)-10,13- dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,- 16,17-tetradecahydro-1H-cyclopenta[a]- phenanthrene-3,7-diol from Chisocheton tomentosus (Meliaceae) Ibrahim A. Najmuldeen, Abdul Hamid Abdul Hadi, Khalijah Awang, Khalit Mohamad and Seik Weng Ng* Department of Chemistry, University of Malaya, Kuala Lumpur, Malaysia Correspondence seikweng@um.edu.my Received 12 October 2008; accepted 13 October 2008 Experimental Crystal data C 29 H 50 O 2 M r = Monoclinic, P2 1 a = (1) Å b = (2) Å c = (4) Å = (1) Data collection Bruker SMART APEX diffractometer Absorption correction: none measured reflections Refinement R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections 575 parameters organic compounds V = (7) Å 3 Z =4 Mo K radiation = 0.07 mm 1 T = 100 (2) K mm 6154 independent reflections 5389 reflections with I > 2(I) R int = restraint H-atom parameters constrained max = 0.46 e Å 3 min = 0.27 e Å 3 Key indicators: single-crystal X-ray study; T = 100 K; mean (C C) = Å; R factor = 0.060; wr factor = 0.172; data-to-parameter ratio = The asymmetric unit of the title compound, C 29 H 50 O 2, contains two molecules; one molecule is linked to the other by two O HO hydrogen bonds, whereas only one of the hydroxy groups of the second molecule is involved in hydrogen bonding. This gives rise to a chain that runs along the a axis of the monoclinic unit cell. Related literature This study is the first on Chisocheton tomentosus. For literature on other Chisocheton species, see: Awang et al. (2007); Bordoloi et al. (1993); Gunning et al. (1994); Inada et al. (1993); Phongmaykin et al. (2008); Tzouros et al. (2004). Table 1 Hydrogen-bond geometry (Å, ). D HA D H HA DA D HA O1 H1OO (3) 178 O2 H2OO (3) 165 O3 H3OO1 i (3) 170 Symmetry code: (i) x 1; y; z. Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publcif (Westrip, 2008). The authors thank the University of Malaya (PPP P A) for supporting this study. Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2810). References Awang, K., Lim, C. S., Mohamad, K., Morita, H., Hirasawa, Y., Takeya, K., Thoison, O. & Hadi, A. H. A. (2007). Bioorg. Med. Chem. 15, Barbour, L. J. (2001). J. Supramol. Chem. 1, Bordoloi, M., Saikia, B., Mathur, R. K. & Goswami, B. N. (1993). Phytochemistry, 34, Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Gunning, P. J., Jeffs, L. B., Isman, M. B. & Towers, G. H. N. (1994). Phytochemistry, 36, Inada, A., Somekawa, M., Murata, H., Nakanishi, T., Tokuda, H., Nishino, H., Iwashima, A., Darnaedi, D. & Jurata, J. (1993). Chem. Pharm. Bull. 41, Phongmaykin, J., Kumamoto, T., Ishikawa, T., Suttisri, R. & Saifah, E. (2008). Arch. Pharm. Res. 31, Sheldrick, G. M. (2008). Acta Cryst. A64, Tzouros, M., Bigler, L., Bienz, S., Hesse, M., Inada, A., Murata, H., Inatomi, Y., Nakanishi, T. & Darnaedi, D. (2004). Helv. Chim. Acta, 87, Westrip, S. P. (2008). publcif. In preparation. Acta Cryst. (2008). E64, o2163 doi: /s Najmuldeen et al. o2163

3 Acta Cryst. (2008). E64, o2163 [ doi: /s ] 17-(5-Ethyl-6-methylheptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,7-diol from Chisocheton tomentosus (Meliaceae) I. A. Najmuldeen, A. H. A. Hadi, K. Awang, K. Mohamad and S. W. Ng Experimental Dried ground bark of Chisocheton tomentosus (3.5 kg) was defatted with hexane for 5 days. The solvent was removed and the plant material dried before being extracted with dichloromethane for another 5 days. The dichloromethane was removed by evaporation to give a crude material (10 g) that was subjected to column chromatography over silica gel. Separation was effected with hexane/dichloromethane (95:5 v/v). The polarity was increased with acetone, and finally with acetone/methanol to give 24 fractions. One of the later fractions was subjected to column chromatography (25:25:50 v/v acetone/dichloromethane/hexane) to give five other fractions. The third fraction yielded colorless crystals when the solvents were allowed to evaporate. Refinement In the absence of significant anomalous dispersion effects, Friedel pairs were averaged. Carbon- and oxygen-bound H-atoms were placed in calculated positions (C H , O H 0.84 Å) and were included in the refinement in the riding model approximation, with U(H) set to U eq (C,O). Figures Fig % Probability displacement ellipsoid plot (Barbour, 2001) of C 29 H 50 O 2. Hydrogen atoms are drawn as spheres of arbitrary radii. 17-(5-Ethyl-6-methylheptan-2-yl)-10,13-dimethyl- 2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1Hcyclopenta[a]phenanthrene-3,7-diol Crystal data C 29 H 50 O 2 F 000 = 960 M r = D x = Mg m 3 sup-1

4 Monoclinic, P2 1 Hall symbol: P 2yb Mo Kα radiation λ = Å a = (1) Å θ = º b = (2) Å c = (4) Å β = (1)º V = (7) Å 3 Z = 4 Cell parameters from 7107 reflections µ = 0.07 mm 1 T = 100 (2) K Prism, colourless mm Data collection Bruker SMART APEX diffractometer Radiation source: fine-focus sealed tube R int = Monochromator: graphite θ max = 27.5º T = 100(2) K θ min = 0.8º ω scans Absorption correction: none 5389 reflections with I > 2σ(I) h = k = measured reflections l = independent reflections Refinement Refinement on F 2 Least-squares matrix: full R[F 2 > 2σ(F 2 )] = Secondary atom site location: difference Fourier map Hydrogen site location: inferred from neighbouring sites H-atom parameters constrained wr(f 2 ) = w = 1/[σ 2 (F o 2 ) + (0.1065P) P] where P = (F o 2 + 2F c 2 )/3 S = 1.11 (Δ/σ) max = reflections Δρ max = 0.46 e Å parameters Δρ min = 0.27 e Å 3 1 restraint Extinction correction: none Primary atom site location: structure-invariant direct methods Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 ) x y z U iso */U eq O (2) (2) (9) (5) H1O * O (3) (2) (9) (6) H2O * O (3) (2) (9) (6) H3O * O (3) (2) (9) (5) H4O * sup-2

5 C (3) (3) (12) (6) H * C (4) (3) (12) (6) H2A * H2B * C (4) (2) (11) (6) C (3) (2) (12) (6) C (4) (3) (12) (6) H5A * H5B * H5C * C (4) (3) (12) (6) H6A * H6B * C (4) (3) (13) (6) H7A * H7B * C (4) (3) (12) (6) H * C (4) (3) (12) (6) H * C (4) (2) (11) (6) H * C (4) (2) (12) (6) H * C (4) (3) (12) (6) H * C (4) (3) (12) (6) C (4) (3) (13) (6) H14A * H14B * H14C * C (4) (3) (13) (7) H15A * H15B * C (4) (2) (13) (7) H16A * H16B * C (4) (3) (13) (7) H17A * H17B * C (4) (3) (13) (7) H18A * H18B * C (4) (3) (13) (6) H * C (4) (3) (14) (7) H * C (5) (3) (17) (9) sup-3

6 H21A * H21B * H21C * C (4) (3) (14) (8) H22A * H22B * C (5) (4) (16) (9) H23A * H23B * C (5) (4) (15) (9) H * C (6) (4) (18) (11) H25A * H25B * C (10) (6) (3) (2) H26A * H26B * H26C * C (5) (5) (17) (11) H * C (8) (6) (3) (16) H28A * H28B * H28C * C (6) (7) (2) (2) H29A * H29B * H29C * C (4) (3) (12) (7) H * C (4) (3) (12) (6) H31A * H31B * C (3) (3) (11) (6) C (3) (3) (11) (6) C (4) (3) (12) (6) H34A * H34B * H34C * C (4) (3) (12) (6) H35A * H35B * C (4) (3) (13) (7) H36A * H36B * C (4) (3) (12) (6) H * C (3) (3) (12) (6) H * sup-4

7 C (3) (2) (11) (5) H * C (3) (2) (11) (6) H * C (3) (3) (11) (6) H * C (4) (3) (11) (6) C (4) (3) (12) (6) H43A * H43B * H43C * C (4) (3) (12) (6) H44A * H44B * C (4) (2) (12) (6) H45A * H45B * C (4) (3) (13) (7) H46A * H46B * C (4) (3) (13) (7) H47A * H47B * C (4) (3) (12) (6) H * C (4) (3) (12) (7) H * C (5) (3) (15) (8) H50A * H50B * H50C * C (4) (3) (13) (7) H51A * H51B * C (5) (4) (15) (10) H52A * H52B * C (5) (4) (15) (9) H * C (6) (5) (2) (13) H54A * H54B * C (9) (6) (3) (19) H55A * H55B * H55C * C (5) (4) (16) (10) H * C (7) (4) (19) (12) sup-5

8 H57A * H57B * H57C * C (6) (5) (2) (13) H58A * H58B * H58C * Atomic displacement parameters (Å 2 ) U 11 U 22 U 33 U 12 U 13 U 23 O (10) (12) (11) (9) (8) (9) O (11) (15) (11) (11) (9) (10) O (10) (16) (11) (11) (8) (11) O (9) (13) (11) (9) (8) (10) C (13) (16) (15) (12) (11) (13) C (15) (14) (16) (12) (12) (12) C (14) (14) (14) (11) (11) (11) C (13) (13) (15) (10) (11) (11) C (14) (16) (16) (12) (12) (12) C (14) (13) (16) (11) (11) (12) C (13) (15) (16) (12) (11) (13) C (17) (15) (15) (13) (12) (11) C (16) (14) (14) (12) (11) (11) C (14) (14) (14) (11) (11) (11) C (13) (13) (14) (11) (11) (11) C (14) (15) (14) (12) (11) (12) C (13) (15) (14) (12) (11) (12) C (14) (16) (16) (12) (12) (13) C (15) (14) (17) (12) (13) (12) C (15) (14) (17) (12) (13) (12) C (17) (17) (16) (14) (13) (13) C (16) (18) (16) (14) (13) (14) C (14) (16) (16) (12) (12) (13) C (15) (16) (17) (13) (12) (13) C (2) (18) (2) (15) (17) (16) C (16) (2) (18) (15) (13) (15) C (2) (3) (2) (18) (16) (19) C (2) (2) (18) (19) (15) (17) C (3) (3) (2) (2) (19) (2) C (5) (4) (4) (4) (4) (3) C (2) (3) (2) (2) (16) (2) C (4) (4) (4) (3) (3) (3) C (3) (6) (3) (3) (2) (4) C (13) (19) (15) (13) (11) (13) C (13) (16) (15) (12) (11) (13) C (13) (15) (14) (11) (10) (12) C (12) (14) (13) (11) (10) (11) sup-6

9 C (13) (16) (15) (12) (11) (13) C (14) (16) (15) (12) (11) (12) C (15) (19) (16) (13) (12) (13) C (14) (14) (15) (11) (11) (12) C (13) (15) (14) (11) (11) (11) C (12) (13) (14) (10) (10) (11) C (12) (14) (13) (10) (10) (11) C (12) (15) (13) (11) (10) (11) C (13) (15) (13) (11) (10) (11) C (14) (17) (15) (13) (11) (13) C (14) (15) (15) (12) (11) (12) C (14) (14) (15) (11) (12) (11) C (15) (18) (16) (13) (12) (13) C (15) (17) (16) (13) (12) (13) C (13) (16) (15) (12) (11) (12) C (15) (17) (14) (13) (12) (13) C (2) (18) (19) (15) (15) (15) C (16) (19) (16) (14) (13) (14) C (19) (3) (19) (19) (15) (18) C (2) (2) (18) (19) (15) (17) C (3) (3) (3) (2) (2) (3) C (5) (4) (4) (4) (3) (4) C (2) (3) (19) (2) (16) (18) C (3) (3) (3) (2) (2) (2) C (2) (3) (3) (2) (2) (3) Geometric parameters (Å, ) O1 C (4) C28 H28C O1 H1O C29 H29A O2 C (4) C29 H29B O2 H2O C29 H29C O3 C (4) C30 C (5) O3 H3O C30 C (5) O4 C (4) C30 H O4 H4O C31 C (4) C1 C (5) C31 H31A C1 C (4) C31 H31B C1 H C32 C (4) C2 C (4) C32 C (4) C2 H2A C33 C (4) C2 H2B C33 C (4) C3 C (4) C33 C (4) C3 C (4) C34 H34A C4 C (4) C34 H34B C4 C (4) C34 H34C C4 C (4) C35 C (4) C5 H5A C35 H35A C5 H5B C35 H35B sup-7

10 C5 H5C C36 H36A C6 C (4) C36 H36B C6 H6A C37 C (4) C6 H6B C37 H C7 H7A C38 C (4) C7 H7B C38 H C8 C (5) C39 C (4) C8 H C39 C (4) C9 C (4) C39 H C9 H C40 C (4) C10 C (4) C40 H C10 C (4) C41 C (4) C10 H C41 C (4) C11 C (4) C41 H C11 H C42 C (4) C12 C (4) C42 C (4) C12 C (4) C42 C (4) C12 H C43 H43A C13 C (4) C43 H43B C13 C (4) C43 H43C C13 C (4) C44 C (4) C14 H14A C44 H44A C14 H14B C44 H44B C14 H14C C45 H45A C15 C (4) C45 H45B C15 H15A C46 C (5) C15 H15B C46 H46A C16 H16A C46 H46B C16 H16B C47 C (5) C17 C (5) C47 H47A C17 H17A C47 H47B C17 H17B C48 C (4) C18 C (5) C48 H C18 H18A C49 C (5) C18 H18B C49 C (4) C19 C (5) C49 H C19 H C50 H50A C20 C (5) C50 H50B C20 C (5) C50 H50C C20 H C51 C (5) C21 H21A C51 H51A C21 H21B C51 H51B C21 H21C C52 C (5) C22 C (5) C52 H52A C22 H22A C52 H52B C22 H22B C53 C (7) C23 C (6) C53 C (6) C23 H23A C53 H C23 H23B C54 C (9) sup-8

11 C24 C (7) C54 H54A C24 C (6) C54 H54B C24 H C55 H55A C25 C (9) C55 H55B C25 H25A C55 H55C C25 H25B C56 C (6) C26 H26A C56 C (7) C26 H26B C56 H C26 H26C C57 H57A C27 C (8) C57 H57B C27 C (6) C57 H57C C27 H C58 H58A C28 H28A C58 H58B C28 H28B C58 H58C C1 O1 H1O H29A C29 H29C C9 O2 H2O H29B C29 H29C C30 O3 H3O O3 C30 C (3) C38 O4 H4O O3 C30 C (3) O1 C1 C (2) C36 C30 C (3) O1 C1 C (3) O3 C30 H C7 C1 C (3) C36 C30 H O1 C1 H C31 C30 H C7 C1 H C32 C31 C (3) C2 C1 H C32 C31 H31A C3 C2 C (3) C30 C31 H31A C3 C2 H2A C32 C31 H31B C1 C2 H2A C30 C31 H31B C3 C2 H2B H31A C31 H31B C1 C2 H2B C37 C32 C (3) H2A C2 H2B C37 C32 C (3) C8 C3 C (3) C31 C32 C (3) C8 C3 C (3) C32 C33 C (2) C2 C3 C (3) C32 C33 C (2) C3 C4 C (2) C34 C33 C (2) C3 C4 C (2) C32 C33 C (2) C5 C4 C (2) C34 C33 C (2) C3 C4 C (2) C35 C33 C (2) C5 C4 C (2) C33 C34 H34A C6 C4 C (2) C33 C34 H34B C4 C5 H5A H34A C34 H34B C4 C5 H5B C33 C34 H34C H5A C5 H5B H34A C34 H34C C4 C5 H5C H34B C34 H34C H5A C5 H5C C36 C35 C (3) H5B C5 H5C C36 C35 H35A C7 C6 C (3) C33 C35 H35A C7 C6 H6A C36 C35 H35B C4 C6 H6A C33 C35 H35B C7 C6 H6B H35A C35 H35B sup-9

12 C4 C6 H6B C30 C36 C (3) H6A C6 H6B C30 C36 H36A C1 C7 C (3) C35 C36 H36A C1 C7 H7A C30 C36 H36B C6 C7 H7A C35 C36 H36B C1 C7 H7B H36A C36 H36B C6 C7 H7B C32 C37 C (3) H7A C7 H7B C32 C37 H C3 C8 C (3) C38 C37 H C3 C8 H O4 C38 C (2) C9 C8 H O4 C38 C (2) O2 C9 C (2) C37 C38 C (2) O2 C9 C (3) O4 C38 H C8 C9 C (3) C37 C38 H O2 C9 H C39 C38 H C8 C9 H C38 C39 C (2) C10 C9 H C38 C39 C (2) C12 C10 C (2) C41 C39 C (2) C12 C10 C (2) C38 C39 H C11 C10 C (2) C41 C39 H C12 C10 H C40 C39 H C11 C10 H C39 C40 C (2) C9 C10 H C39 C40 C (2) C10 C11 C (2) C45 C40 C (2) C10 C11 C (2) C39 C40 H C16 C11 C (2) C45 C40 H C10 C11 H C33 C40 H C16 C11 H C39 C41 C (3) C4 C11 H C39 C41 C (2) C10 C12 C (2) C46 C41 C (2) C10 C12 C (3) C39 C41 H C13 C12 C (2) C46 C41 H C10 C12 H C42 C41 H C13 C12 H C44 C42 C (2) C17 C12 H C44 C42 C (2) C12 C13 C (2) C43 C42 C (3) C12 C13 C (3) C44 C42 C (3) C15 C13 C (3) C43 C42 C (2) C12 C13 C (2) C41 C42 C (2) C15 C13 C (3) C42 C43 H43A C14 C13 C (2) C42 C43 H43B C13 C14 H14A H43A C43 H43B C13 C14 H14B C42 C43 H43C H14A C14 H14B H43A C43 H43C C13 C14 H14C H43B C43 H43C H14A C14 H14C C42 C44 C (3) H14B C14 H14C C42 C44 H44A C16 C15 C (3) C45 C44 H44A C16 C15 H15A C42 C44 H44B sup-10

13 C13 C15 H15A C45 C44 H44B C16 C15 H15B H44A C44 H44B C13 C15 H15B C44 C45 C (2) H15A C15 H15B C44 C45 H45A C15 C16 C (3) C40 C45 H45A C15 C16 H16A C44 C45 H45B C11 C16 H16A C40 C45 H45B C15 C16 H16B H45A C45 H45B C11 C16 H16B C41 C46 C (3) H16A C16 H16B C41 C46 H46A C12 C17 C (3) C47 C46 H46A C12 C17 H17A C41 C46 H46B C18 C17 H17A C47 C46 H46B C12 C17 H17B H46A C46 H46B C18 C17 H17B C46 C47 C (2) H17A C17 H17B C46 C47 H47A C17 C18 C (3) C48 C47 H47A C17 C18 H18A C46 C47 H47B C19 C18 H18A C48 C47 H47B C17 C18 H18B H47A C47 H47B C19 C18 H18B C49 C48 C (3) H18A C18 H18B C49 C48 C (3) C20 C19 C (3) C47 C48 C (3) C20 C19 C (3) C49 C48 H C18 C19 C (3) C47 C48 H C20 C19 H C42 C48 H C18 C19 H C50 C49 C (3) C13 C19 H C50 C49 C (3) C22 C20 C (3) C51 C49 C (3) C22 C20 C (3) C50 C49 H C21 C20 C (3) C51 C49 H C22 C20 H C48 C49 H C21 C20 H C49 C50 H50A C19 C20 H C49 C50 H50B C20 C21 H21A H50A C50 H50B C20 C21 H21B C49 C50 H50C H21A C21 H21B H50A C50 H50C C20 C21 H21C H50B C50 H50C H21A C21 H21C C52 C51 C (3) H21B C21 H21C C52 C51 H51A C23 C22 C (3) C49 C51 H51A C23 C22 H22A C52 C51 H51B C20 C22 H22A C49 C51 H51B C23 C22 H22B H51A C51 H51B C20 C22 H22B C51 C52 C (3) H22A C22 H22B C51 C52 H52A C22 C23 C (3) C53 C52 H52A C22 C23 H23A C51 C52 H52B C24 C23 H23A C53 C52 H52B sup-11

14 C22 C23 H23B H52A C52 H52B C24 C23 H23B C54 C53 C (4) H23A C23 H23B C54 C53 C (4) C27 C24 C (3) C52 C53 C (4) C27 C24 C (4) C54 C53 H C25 C24 C (4) C52 C53 H C27 C24 H C56 C53 H C25 C24 H C55 C54 C (5) C23 C24 H C55 C54 H54A C26 C25 C (4) C53 C54 H54A C26 C25 H25A C55 C54 H54B C24 C25 H25A C53 C54 H54B C26 C25 H25B H54A C54 H54B C24 C25 H25B C54 C55 H55A H25A C25 H25B C54 C55 H55B C25 C26 H26A H55A C55 H55B C25 C26 H26B C54 C55 H55C H26A C26 H26B H55A C55 H55C C25 C26 H26C H55B C55 H55C H26A C26 H26C C58 C56 C (4) H26B C26 H26C C58 C56 C (4) C28 C27 C (4) C53 C56 C (4) C28 C27 C (5) C58 C56 H C24 C27 C (5) C53 C56 H C28 C27 H C57 C56 H C24 C27 H C56 C57 H57A C29 C27 H C56 C57 H57B C27 C28 H28A H57A C57 H57B C27 C28 H28B C56 C57 H57C H28A C28 H28B H57A C57 H57C C27 C28 H28C H57B C57 H57C H28A C28 H28C C56 C58 H58A H28B C28 H28C C56 C58 H58B C27 C29 H29A H58A C58 H58B C27 C29 H29B C56 C58 H58C H29A C29 H29B H58A C58 H58C C27 C29 H29C H58B C58 H58C O1 C1 C2 C (2) O3 C30 C31 C (2) C7 C1 C2 C (3) C36 C30 C31 C (3) C1 C2 C3 C (3) C30 C31 C32 C (3) C1 C2 C3 C (3) C30 C31 C32 C (3) C8 C3 C4 C (3) C37 C32 C33 C (3) C2 C3 C4 C (3) C31 C32 C33 C (3) C8 C3 C4 C (3) C37 C32 C33 C (3) C2 C3 C4 C (3) C31 C32 C33 C (3) C8 C3 C4 C (4) C37 C32 C33 C (4) C2 C3 C4 C (2) C31 C32 C33 C (2) C3 C4 C6 C (3) C32 C33 C35 C (3) C5 C4 C6 C (3) C34 C33 C35 C (3) sup-12

15 C11 C4 C6 C (2) C40 C33 C35 C (2) O1 C1 C7 C (2) O3 C30 C36 C (3) C2 C1 C7 C (3) C31 C30 C36 C (3) C4 C6 C7 C (3) C33 C35 C36 C (3) C2 C3 C8 C (3) C31 C32 C37 C (3) C4 C3 C8 C9 2.0 (5) C33 C32 C37 C (5) C3 C8 C9 O (3) C32 C37 C38 O (3) C3 C8 C9 C (4) C32 C37 C38 C (4) O2 C9 C10 C (3) O4 C38 C39 C (3) C8 C9 C10 C (3) C37 C38 C39 C (2) O2 C9 C10 C (3) O4 C38 C39 C (3) C8 C9 C10 C (3) C37 C38 C39 C (3) C12 C10 C11 C (3) C38 C39 C40 C (2) C9 C10 C11 C (3) C41 C39 C40 C (3) C12 C10 C11 C (2) C38 C39 C40 C (3) C9 C10 C11 C (3) C41 C39 C40 C (2) C3 C4 C11 C (3) C32 C33 C40 C (3) C5 C4 C11 C (3) C34 C33 C40 C (3) C6 C4 C11 C (2) C35 C33 C40 C (2) C3 C4 C11 C (2) C32 C33 C40 C (2) C5 C4 C11 C (3) C34 C33 C40 C (3) C6 C4 C11 C (3) C35 C33 C40 C (3) C11 C10 C12 C (3) C38 C39 C41 C (3) C9 C10 C12 C (2) C40 C39 C41 C (3) C11 C10 C12 C (3) C38 C39 C41 C (2) C9 C10 C12 C (3) C40 C39 C41 C (3) C10 C12 C13 C (3) C39 C41 C42 C (3) C17 C12 C13 C (3) C46 C41 C42 C (2) C10 C12 C13 C (3) C39 C41 C42 C (3) C17 C12 C13 C (3) C46 C41 C42 C (3) C10 C12 C13 C (2) C39 C41 C42 C (2) C17 C12 C13 C (3) C46 C41 C42 C (3) C12 C13 C15 C (3) C43 C42 C44 C (3) C14 C13 C15 C (3) C41 C42 C44 C (3) C19 C13 C15 C (3) C48 C42 C44 C (3) C13 C15 C16 C (4) C42 C44 C45 C (3) C10 C11 C16 C (4) C39 C40 C45 C (3) C4 C11 C16 C (3) C33 C40 C45 C (2) C10 C12 C17 C (3) C39 C41 C46 C (3) C13 C12 C17 C (3) C42 C41 C46 C (3) C12 C17 C18 C (3) C41 C46 C47 C (3) C17 C18 C19 C (3) C46 C47 C48 C (3) C17 C18 C19 C (3) C46 C47 C48 C (3) C12 C13 C19 C (3) C44 C42 C48 C (3) C15 C13 C19 C (4) C43 C42 C48 C (4) C14 C13 C19 C (4) C41 C42 C48 C (3) C12 C13 C19 C (3) C44 C42 C48 C (3) C15 C13 C19 C (3) C43 C42 C48 C (3) C14 C13 C19 C (3) C41 C42 C48 C (3) sup-13

16 C18 C19 C20 C (4) C47 C48 C49 C (3) C13 C19 C20 C (3) C42 C48 C49 C (4) C18 C19 C20 C (3) C47 C48 C49 C (3) C13 C19 C20 C (4) C42 C48 C49 C (3) C21 C20 C22 C (4) C50 C49 C51 C (4) C19 C20 C22 C (3) C48 C49 C51 C (3) C20 C22 C23 C (3) C49 C51 C52 C (4) C22 C23 C24 C (5) C51 C52 C53 C (5) C22 C23 C24 C (4) C51 C52 C53 C (5) C27 C24 C25 C (5) C52 C53 C54 C (6) C23 C24 C25 C (6) C56 C53 C54 C (4) C25 C24 C27 C (5) C54 C53 C56 C (5) C23 C24 C27 C (5) C52 C53 C56 C (4) C25 C24 C27 C (5) C54 C53 C56 C (4) C23 C24 C27 C (4) C52 C53 C56 C (5) Hydrogen-bond geometry (Å, ) D H A D H H A D A D H A O1 H1O O (3) 178 O2 H2O O (3) 165 O3 H3O O1 i (3) 170 Symmetry codes: (i) x 1, y, z. sup-14

17 Fig. 1 sup-15

18 Fig. 2 sup-16

Experimental. Crystal data. C 22 H 28 N 2 O 3 CH 4 O M r = Monoclinic, C2=c a = (4) Å b = (2) Å c = (5) Å = 96.

Experimental. Crystal data. C 22 H 28 N 2 O 3 CH 4 O M r = Monoclinic, C2=c a = (4) Å b = (2) Å c = (5) Å = 96. organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 N 0 -(3,5-Di-tert-butyl-4-hydroxybenzylidene)-2-hydroxybenzohydrazide methanol solvate Wagee A. Yehye, Azhar Ariffin*