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.

Transcription

1 organic compounds Acta Crystallographica Section E Structure Reports Online ISSN N 0 -(3,5-Di-tert-butyl-4-hydroxybenzylidene)-2-hydroxybenzohydrazide methanol solvate Wagee A. Yehye, Azhar Ariffin* and Seik Weng Ng Department of Chemistry, University of Malaya, Kuala Lumpur, Malaysia Correspondence azahar70@um.edu.my Received 2 July 2008; accepted 4 July 2008 Key indicators: single-crystal X-ray study; T = 100 K; mean (C C) = Å; R factor = 0.075; wr factor = 0.239; data-to-parameter ratio = 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 = (3) Data collection Bruker SMART APEX diffractometer Absorption correction: none measured reflections Refinement R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections V = 8911 (2) Å 3 Z =16 Mo K radiation = 0.08 mm 1 T = 100 (2) K mm 7825 independent reflections 4711 reflections with I > 2(I) R int = parameters H-atom parameters constrained max = 0.74 e Å 3 min = 0.58 e Å 3 The asymmetric unit of the title compound, C 22 H 28 - N 2 O 3 CH 4 O, consists of two independent Schiff base molecules and two independent methanol solvent molecules. In one Schiff base molecule, the 2-hydroxy group forms an intramolecular hydrogen bond with the amide O atom, whereas in the other Schiff base molecule, the 2-hydroxysubstituted benzene ring is oriented so that the 2-hydroxy group serves as hydrogen-bond acceptor for the amide NH group. In the crystal structure, Schiff base molecules interact with methanol solvent to furnish a hydrogen-bonded chain. Related literature For references to other crystal structures of substituted benzylidene-2-hydroxybenzohydrazides, see: Yehye et al. (2008). Table 1 Hydrogen-bond geometry (Å, ). D HA D H HA DA D HA O1 H1oO (4) 147 O4 H4oO (4) 167 N1 H1nO5 i (4) 132 N3 H3nO (4) 137 O7 H7oN (4) 148 O8 H8oO (5) 140 Symmetry code: (i) x; y 1; 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 acknowledge th SAGA grant (No ) for supporting this study, and the University of Malaya for the purchase of the diffractometer. Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2656). References Barbour, L. J. (2001). J. Supramol. Chem. 1, Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Sheldrick, G. M. (2008). Acta Cryst. A64, Westrip, S. P. (2008). publcif. In preparation. Yehye, W. A., Ariffin, A. & Ng, S. W. (2008). Acta Cryst. E64, o961. o1452 Yehye et al. doi: /s Acta Cryst. (2008). E64, o1452

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3 Acta Cryst. (2008). E64, o1452 [ doi: /s ] N'-(3,5-Di-tert-butyl-4-hydroxybenzylidene)-2-hydroxybenzohydrazide methanol solvate W. A. Yehye, A. Ariffin and S. W. Ng Comment The crystal structures of a number of substituted benzylidene-2-hydroxybenzohydrazides have been reported, along with that of the 2,4-dimethoxy derivative, which crystallizes as an ethanol solvate (Yehye et al., 2008 and references cited within). In the title compound, the asymmetric unit consists of two Schiff-base and two solvent molecules. In one Schiff base molecule, the hydroxy group forms an intramolecular hydrogen bond with the amido C=O oxygen atom whereas in the other Schiff base molecule, the phenylene ring is rotated so that the 2-hydroxy group now serves as hydrogen-bond acceptor to the amido NH nitrogen atom (Fig. 1). The Schiff-base molecules interact with the two lattice methanol molecules to furnish a hydrogen-bonded chain. Experimental 2-Hydroxybenzohydrazide (0.5 g, 4 mmol) and 3,5-di-tert-butyl-4-hydroxybenzaldehyde (0.9 g, 4 mmol) were heated in ethanol (30 ml) for 2 h. The solvent was removed by evaporation and the product recrystallized from methanol. Refinement Carbon-bound H-atoms were placed in calculated positions (C H 0.95 to 0.98 Å) and were included in the refinement in the riding model approximation, with U(H) set to U(C). The oxygen- and nitrogen-bound H-atoms were similarly treated as riding (O H 0.84 Å, N H 0.88 Å). Figures Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C 21 H 26 N 2 O 3. CH3 OH at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radiius. N'-(3,5-Di-tert-butyl-4-hydroxybenzylidene)-2-hydroxybenzohydrazide methanol solvate Crystal data C 22 H 28 N 2 O 3 CH 4 O F 000 = 3456 M r = Monoclinic, C2/c D x = Mg m 3 Mo Kα radiation λ = Å sup-1

4 Hall symbol: -C 2yc Cell parameters from 2005 reflections a = (4) Å θ = º b = (2) Å µ = 0.08 mm 1 c = (5) Å T = 100 (2) K β = (3)º Block, colorless V = 8911 (2) Å mm Z = 16 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 = 1.2º ω scans Absorption correction: none 4711 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 2 o ) + (0.1232P) 2 ] where P = (F 2 o + 2F 2 c )/3 S = 1.09 (Δ/σ) max = reflections Δρ max = 0.74 e Å parameters Δρ min = 0.58 e Å 3 Primary atom site location: structure-invariant direct methods Extinction correction: none Special details Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 ) x y z U iso */U eq O (12) (2) (9) (7) H1O * O (11) (2) (8) (7) sup-2

5 O (11) (2) (8) (7) H3O * O (12) (2) (10) (8) H4O * O (11) (2) (8) (6) O (11) (2) (9) (7) H6O * O (15) (3) (11) (10) H7O * O (18) (3) (13) (12) H8O * N (12) (2) (9) (7) H1N * N (12) (3) (9) (7) N (12) (3) (9) (7) H3N * N (12) (2) (9) (7) C (15) (3) (12) (9) C (16) (3) (12) (9) H * C (15) (3) (12) (9) H * C (16) (3) (11) (9) H * C (15) (3) (11) (9) H * C (15) (3) (11) (8) C (15) (3) (11) (8) C (15) (3) (11) (8) H * C (14) (3) (11) (8) C (14) (3) (11) (8) H * C (15) (3) (11) (8) C (15) (3) (11) (9) C (14) (3) (11) (8) C (14) (3) (11) (8) H * C (16) (3) (12) (9) C (18) (3) (13) (11) H16A * H16B * H16C * C (17) (4) (12) (10) H17A * H17B * H17C * C (17) (4) (13) (11) H18A * sup-3

6 H18B * H18C * C (15) (3) (12) (9) C (18) (4) (13) (11) H20A * H20B * H20C * C (17) (3) (13) (10) H21A * H21B * H21C * C (15) (3) (12) (9) H22A * H22B * H22C * C (15) (3) (11) (8) C (15) (3) (11) (9) H * C (16) (4) (12) (9) H * C (16) (4) (12) (9) H * C (15) (3) (11) (9) H * C (15) (3) (11) (8) C (15) (3) (10) (8) C (15) (3) (10) (8) H * C (14) (3) (10) (8) C (14) (3) (10) (8) H * C (14) (3) (10) (8) C (15) (3) (11) (8) C (15) (3) (11) (8) C (15) (3) (11) (8) H * C (15) (3) (11) (9) C (19) (3) (14) (12) H38A * H38B * H38C * C (19) (4) (15) (13) H39A * H39B * H39C * C (17) (3) (12) (10) H40A * H40B * H40C * sup-4

7 C (16) (3) (12) (10) C (17) (4) (13) (11) H42A * H42B * H42C * C (18) (4) (13) (11) H43A * H43B * H43C * C (19) (3) (16) (13) H44A * H44B * H44C * C (2) (4) (17) (16) H45A * H45B * H45C * C (4) (6) (2) (3) H46A * H46B * H46C * Atomic displacement parameters (Å 2 ) U 11 U 22 U 33 U 12 U 13 U 23 O (18) (14) (18) (12) (13) (13) O (18) (14) (17) (12) (13) (12) O (17) (16) (16) (12) (12) (13) O (18) (16) (2) (13) (15) (16) O (16) (14) (16) (11) (12) (12) O (16) (17) (18) (13) (13) (14) O (3) (19) (2) (17) (19) (17) O (3) (2) (3) (19) (3) (2) N (17) (16) (16) (13) (13) (13) N (17) (16) (16) (13) (13) (14) N (17) (16) (18) (13) (14) (14) N (16) (16) (17) (13) (13) (14) C (2) (2) (2) (16) (17) (17) C (2) (2) (2) (18) (18) (18) C (2) (2) (2) (18) (17) (19) C (2) (2) (2) (17) (17) (18) C (2) (19) (2) (16) (17) (17) C (2) (18) (19) (15) (15) (15) C (2) (2) (2) (16) (16) (17) C (2) (19) (19) (16) (15) (16) C (2) (19) (2) (15) (15) (16) C (2) (18) (2) (15) (16) (16) C (2) (2) (2) (16) (16) (17) sup-5

8 C (2) (2) (2) (16) (16) (17) C (19) (2) (2) (15) (15) (16) C (2) (18) (2) (15) (16) (16) C (2) (2) (2) (17) (17) (18) C (3) (2) (3) (19) (2) (19) C (2) (2) (2) (19) (19) (19) C (3) (3) (3) (2) (2) (2) C (2) (2) (2) (16) (16) (18) C (3) (3) (3) (2) (2) (2) C (2) (2) (3) (18) (2) (19) C (2) (2) (2) (17) (17) (19) C (2) (2) (2) (16) (16) (16) C (2) (2) (2) (17) (17) (17) C (2) (2) (2) (18) (17) (19) C (2) (2) (2) (18) (17) (19) C (2) (2) (2) (16) (16) (17) C (2) (2) (19) (16) (15) (16) C (2) (2) (19) (16) (15) (16) C (2) (19) (2) (16) (16) (16) C (2) (19) (19) (15) (15) (16) C (2) (19) (19) (15) (15) (16) C (2) (2) (19) (16) (15) (16) C (2) (2) (2) (16) (15) (17) C (2) (2) (2) (16) (16) (16) C (2) (19) (2) (16) (16) (16) C (2) (2) (2) (16) (16) (17) C (3) (2) (3) (19) (2) (2) C (3) (3) (3) (2) (2) (2) C (3) (2) (2) (18) (19) (19) C (2) (2) (2) (17) (19) (19) C (3) (3) (3) (2) (2) (2) C (3) (3) (3) (2) (2) (2) C (3) (2) (4) (2) (3) (2) C (5) (3) (4) (3) (3) (3) C (9) (4) (6) (5) (6) (4) Geometric parameters (Å, ) O1 C (4) C20 H20B O1 H1O C20 H20C O2 C (4) C21 H21A O3 C (4) C21 H21B O3 H3O C21 H21C O4 C (4) C22 H22A O4 H4O C22 H22B O5 C (4) C22 H22C O6 C (4) C23 C (5) O6 H6O C23 C (5) O7 C (6) C24 C (5) sup-6

9 O7 H7O C24 H O8 C (7) C25 C (6) O8 H8O C25 H N1 C (4) C26 C (5) N1 N (4) C26 H N1 H1N C27 C (5) N2 C (4) C27 H N3 C (4) C28 C (5) N3 N (4) C30 C (5) N3 H3N C30 H N4 C (4) C31 C (5) C1 C (5) C31 C (5) C1 C (5) C32 C (5) C2 C (5) C32 H C2 H C33 C (5) C3 C (5) C33 C (5) C3 H C34 C (5) C4 C (5) C35 C (5) C4 H C35 C (5) C5 C (5) C36 H C5 H C37 C (5) C6 C (5) C37 C (5) C8 C (5) C37 C (5) C8 H C38 H38A C9 C (5) C38 H38B C9 C (5) C38 H38C C10 C (5) C39 H39A C10 H C39 H39B C11 C (5) C39 H39C C11 C (5) C40 H40A C12 C (5) C40 H40B C13 C (5) C40 H40C C13 C (5) C41 C (5) C14 H C41 C (6) C15 C (5) C41 C (6) C15 C (5) C42 H42A C15 C (5) C42 H42B C16 H16A C42 H42C C16 H16B C43 H43A C16 H16C C43 H43B C17 H17A C43 H43C C17 H17B C44 H44A C17 H17C C44 H44B C18 H18A C44 H44C C18 H18B C45 H45A C18 H18C C45 H45B C19 C (5) C45 H45C C19 C (5) C46 H46A C19 C (5) C46 H46B sup-7

10 C20 H20A C46 H46C C1 O1 H1O H22B C22 H22C C12 O3 H3O O4 C23 C (3) C23 O4 H4O O4 C23 C (3) C34 O6 H6O C24 C23 C (3) C45 O7 H7O C23 C24 C (4) C46 O8 H8O C23 C24 H C7 N1 N (3) C25 C24 H C7 N1 H1N C26 C25 C (4) N2 N1 H1N C26 C25 H C8 N2 N (3) C24 C25 H C29 N3 N (3) C25 C26 C (4) C29 N3 H3N C25 C26 H N4 N3 H3N C27 C26 H C30 N4 N (3) C26 C27 C (4) O1 C1 C (3) C26 C27 H O1 C1 C (3) C28 C27 H C2 C1 C (3) C27 C28 C (3) C3 C2 C (4) C27 C28 C (3) C3 C2 H C23 C28 C (3) C1 C2 H O5 C29 N (3) C2 C3 C (4) O5 C29 C (3) C2 C3 H N3 C29 C (3) C4 C3 H N4 C30 C (3) C5 C4 C (4) N4 C30 H C5 C4 H C31 C30 H C3 C4 H C36 C31 C (3) C4 C5 C (3) C36 C31 C (3) C4 C5 H C32 C31 C (3) C6 C5 H C33 C32 C (3) C5 C6 C (3) C33 C32 H C5 C6 C (3) C31 C32 H C1 C6 C (3) C32 C33 C (3) O2 C7 N (3) C32 C33 C (3) O2 C7 C (3) C34 C33 C (3) N1 C7 C (3) O6 C34 C (3) N2 C8 C (3) O6 C34 C (3) N2 C8 H C35 C34 C (3) C9 C8 H C36 C35 C (3) C14 C9 C (3) C36 C35 C (3) C14 C9 C (3) C34 C35 C (3) C10 C9 C (3) C31 C36 C (3) C11 C10 C (3) C31 C36 H C11 C10 H C35 C36 H C9 C10 H C38 C37 C (3) C10 C11 C (3) C38 C37 C (3) C10 C11 C (3) C40 C37 C (3) C12 C11 C (3) C38 C37 C (4) O3 C12 C (3) C40 C37 C (3) sup-8

11 O3 C12 C (3) C33 C37 C (3) C11 C12 C (3) C37 C38 H38A C14 C13 C (3) C37 C38 H38B C14 C13 C (3) H38A C38 H38B C12 C13 C (3) C37 C38 H38C C13 C14 C (3) H38A C38 H38C C13 C14 H H38B C38 H38C C9 C14 H C37 C39 H39A C16 C15 C (3) C37 C39 H39B C16 C15 C (3) H39A C39 H39B C18 C15 C (3) C37 C39 H39C C16 C15 C (3) H39A C39 H39C C18 C15 C (3) H39B C39 H39C C17 C15 C (3) C37 C40 H40A C15 C16 H16A C37 C40 H40B C15 C16 H16B H40A C40 H40B H16A C16 H16B C37 C40 H40C C15 C16 H16C H40A C40 H40C H16A C16 H16C H40B C40 H40C H16B C16 H16C C44 C41 C (3) C15 C17 H17A C44 C41 C (4) C15 C17 H17B C35 C41 C (3) H17A C17 H17B C44 C41 C (4) C15 C17 H17C C35 C41 C (3) H17A C17 H17C C43 C41 C (3) H17B C17 H17C C41 C42 H42A C15 C18 H18A C41 C42 H42B C15 C18 H18B H42A C42 H42B H18A C18 H18B C41 C42 H42C C15 C18 H18C H42A C42 H42C H18A C18 H18C H42B C42 H42C H18B C18 H18C C41 C43 H43A C21 C19 C (3) C41 C43 H43B C21 C19 C (3) H43A C43 H43B C20 C19 C (3) C41 C43 H43C C21 C19 C (3) H43A C43 H43C C20 C19 C (3) H43B C43 H43C C13 C19 C (3) C41 C44 H44A C19 C20 H20A C41 C44 H44B C19 C20 H20B H44A C44 H44B H20A C20 H20B C41 C44 H44C C19 C20 H20C H44A C44 H44C H20A C20 H20C H44B C44 H44C H20B C20 H20C O7 C45 H45A C19 C21 H21A O7 C45 H45B C19 C21 H21B H45A C45 H45B H21A C21 H21B O7 C45 H45C C19 C21 H21C H45A C45 H45C H21A C21 H21C H45B C45 H45C sup-9

12 H21B C21 H21C O8 C46 H46A C19 C22 H22A O8 C46 H46B C19 C22 H22B H46A C46 H46B H22A C22 H22B O8 C46 H46C C19 C22 H22C H46A C46 H46C H22A C22 H22C H46B C46 H46C C7 N1 N2 C (3) C12 C13 C19 C (4) C29 N3 N4 C (3) O4 C23 C24 C (4) O1 C1 C2 C (3) C28 C23 C24 C (6) C6 C1 C2 C3 1.6 (6) C23 C24 C25 C (6) C1 C2 C3 C4 0.8 (6) C24 C25 C26 C (6) C2 C3 C4 C5 2.0 (6) C25 C26 C27 C (6) C3 C4 C5 C6 0.7 (6) C26 C27 C28 C (5) C4 C5 C6 C1 1.7 (5) C26 C27 C28 C (3) C4 C5 C6 C (3) O4 C23 C28 C (3) O1 C1 C6 C (3) C24 C23 C28 C (5) C2 C1 C6 C5 2.8 (5) O4 C23 C28 C (6) O1 C1 C6 C7 1.1 (5) C24 C23 C28 C (3) C2 C1 C6 C (3) N4 N3 C29 O5 0.3 (5) N2 N1 C7 O2 1.4 (5) N4 N3 C29 C (3) N2 N1 C7 C (3) C27 C28 C29 O5 3.4 (5) C5 C6 C7 O (3) C23 C28 C29 O (3) C1 C6 C7 O2 7.5 (5) C27 C28 C29 N (3) C5 C6 C7 N1 9.0 (5) C23 C28 C29 N3 3.1 (5) C1 C6 C7 N (3) N3 N4 C30 C (3) N1 N2 C8 C (3) N4 C30 C31 C (3) N2 C8 C9 C (3) N4 C30 C31 C (6) N2 C8 C9 C (5) C36 C31 C32 C (5) C14 C9 C10 C (5) C30 C31 C32 C (3) C8 C9 C10 C (3) C31 C32 C33 C (5) C9 C10 C11 C (5) C31 C32 C33 C (3) C9 C10 C11 C (3) C32 C33 C34 O (3) C10 C11 C12 O (3) C37 C33 C34 O6 0.4 (5) C15 C11 C12 O3 3.8 (5) C32 C33 C34 C (5) C10 C11 C12 C (5) C37 C33 C34 C (3) C15 C11 C12 C (3) O6 C34 C35 C (3) O3 C12 C13 C (3) C33 C34 C35 C (6) C11 C12 C13 C (5) O6 C34 C35 C (6) O3 C12 C13 C (5) C33 C34 C35 C (3) C11 C12 C13 C (3) C32 C31 C36 C (5) C12 C13 C14 C9 1.1 (5) C30 C31 C36 C (3) C19 C13 C14 C (3) C34 C35 C36 C (5) C10 C9 C14 C (5) C41 C35 C36 C (3) C8 C9 C14 C (3) C32 C33 C37 C (5) C10 C11 C15 C (5) C34 C33 C37 C (3) C12 C11 C15 C (3) C32 C33 C37 C (4) C10 C11 C15 C (4) C34 C33 C37 C (5) C12 C11 C15 C (5) C32 C33 C37 C (4) C10 C11 C15 C (4) C34 C33 C37 C (5) sup-10

13 C12 C11 C15 C (4) C36 C35 C41 C (5) C14 C13 C19 C (5) C34 C35 C41 C (4) C12 C13 C19 C (3) C36 C35 C41 C (4) C14 C13 C19 C (4) C34 C35 C41 C (5) C12 C13 C19 C (4) C36 C35 C41 C (4) C14 C13 C19 C (4) C34 C35 C41 C (5) Hydrogen-bond geometry (Å, ) D H A D H H A D A D H A O1 H1o O (4) 147 O4 H4o O (4) 167 N1 H1n O5 i (4) 132 N3 H3n O (4) 137 O7 H7o N (4) 148 O8 H8o O (5) 140 Symmetry codes: (i) x, y 1, z. sup-11

14 Fig. 1 sup-12