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Acta Crystallogr Sect E Struct Rep Online. 2008 July 1; 64(Pt 7): o1246–o1247.
Published online 2008 June 13. doi:  10.1107/S1600536808014487
PMCID: PMC2961737

2-((E)-{2-[(1E)-(2,4-Dihydroxy­benzyl­idene)amino]phen­yl}iminiometh­yl)-5-hydroxy­phenolate methanol solvate

Abstract

The asymmetric unit of the title compound, C20H16N2O4·CH3OH, contains two Schiff base zwitterions and two methanol solvent mol­ecules. The dihedral angles between the central benzene ring and the two outer benzene rings of the Schiff base are 2.57 (7) and 52.30 (7)° in one mol­ecule and 5.83 (7) and 49.82 (7)° in the other mol­ecule. Intra­molecular O—H(...)N and N—H(...)O hydrogen bonds generate S(6) ring motifs, whereas intra­molecular N—H(...)N hydrogen bonds generate S(5) ring motifs. In the crystal structure, O—H(...)O, hydrogen bonds and weak C—H(...)O inter­actions link the mol­ecules into one-dimensional chains along the b-axis direction and are further connected by O—H(...)O and weak C—H(...)O inter­actions into a three-dimensional network. C—H(...)π and π–π inter­actions [centroid–centroid distances = 3.6228 (9) and 3.6881 (9) Å] are also observed in the crystal structure.

Related literature

For bond-length data, see: Allen et al. (1987 [triangle]). For details of hydrogen-bond motifs, see: Bernstein et al. (1995 [triangle]). For related structures, see, for example: Eltayeb et al. (2007a [triangle],b [triangle]). For background to applications of Schiff base ligands, see, for example: Dao et al. (2000 [triangle]); Eltayeb & Ahmed (2005a [triangle],b [triangle]); Fakhari et al. (2005 [triangle]); Karthikeyan et al. (2006 [triangle]); Sriram et al. (2006 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1246-scheme1.jpg

Experimental

Crystal data

  • C20H16N2O4·CH4O
  • M r = 380.39
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1246-efi1.jpg
  • a = 8.3672 (2) Å
  • b = 11.0813 (2) Å
  • c = 20.3217 (3) Å
  • α = 89.313 (1)°
  • β = 80.309 (1)°
  • γ = 79.641 (1)°
  • V = 1826.73 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 100.0 (1) K
  • 0.50 × 0.34 × 0.17 mm

Data collection

  • Bruker SMART APEX2 CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.952, T max = 0.984
  • 42593 measured reflections
  • 10651 independent reflections
  • 7203 reflections with I > 2σ(I)’
  • R int = 0.034

Refinement

  • R[F 2 > 2σ(F 2)] = 0.056
  • wR(F 2) = 0.162
  • S = 1.05
  • 10651 reflections
  • 515 parameters
  • H-atom parameters constrained
  • Δρmax = 0.44 e Å−3
  • Δρmin = −0.34 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 [triangle]); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808014487/sj2499sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808014487/sj2499Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors thank the Malaysian Government, the Ministry of Science, Technology and Innovation (MOSTI) and Universiti Sains Malaysia for E-Science Fund and RU research grants (PKIMIA/613308, PKIMIA/815002, 203/PKIMIA/671083) and a fellowship for NEE. The International University of Africa (Sudan) is acknowledged for providing study leave to NEE. The authors also thank Universiti Sains Malaysia for the Fundamental Research Grant Scheme (FRGS) grant No. 203/PFIZIK/671064.

supplementary crystallographic information

Comment

Schiff bases have received much attention because of their potential applications with some of these compounds exhibiting various pharmacological activities, as noted by their anticancer (Dao et al., 2000), anti-HIV (Sriram et al., 2006), antibacterial and antifungal (Karthikeyan et al., 2006) properties. In addition, some of them may be used as analytical reagents for the determination of trace elements (Eltayeb & Ahmed, 2005a,b) such as nickel in some natural food products (Fakhari et al., 2005). We reported the crystal structures of 5,5'-Dimethoxy-2,2'-[1,2-phenylenebis(nitrilomethylidyne)diphenol (Eltayeb et al., 2007a) and 4,4'-Dimethoxy-2,2'-[1,2-phenylenebis(nitrilomethylidyne)diphenol (Eltayeb et al., 2007b) and we report here the structure of the title compound (I), a closely-related Schiff base.

The asymmetric unit of (I) (Fig. 1) contains two Schiff base zwitterions and two methanol molecules (A and B). The zwitterion results from protonation of the imine N1A and N1B atoms with protons from the O2A and O2B hydroxy groups resulting in the formation of iminium and hydroxyphenolate groups. In the structure, the hydroxyphenolate ring (C1–C6/O1-O2) is nearly coplanar with the phenyl ring (C8–C13) as indicated by the dihedral angles between these two rings being 2.57 (7)° in molecule A and 5.83 (7)° in molecule B and the torsion angle C8/N1/C7/C6 = 179.33 (2)° in molecule A and 178.07 (12)° in molecule B. The C8–C13 phenyl ring makes a dihedral angle of 52.30 (7)° with the dihydroxyphenyl ring (C15–C20/O3–O4) in molecule A [49.82 (7)° in molecule B].

Intramolecular hydrogen bonds, O3A—H3OA···N2A, N1A—H1NA···O2A, O3B—H3OB···N2B and N1B—H1NB···O2B (Table 1) generate S(6) ring motifs whereas N1A—H1NA···N2A and N1B—H1NB···N2B generate S(5) ring motifs (Bernstein et al., 1995). Bond lengths and angles are in normal ranges (Allen et al., 1987) and comparable to those in related structures (Eltayeb et al., 2007a,b). In the crystal packing (Fig. 2), O—H···O, hydrogen bonds and weak C—H···O interactions (Table 1) link the molecules into one dimensional chains along the b direction and are further connected by O—H···O and weak C—H···O interactions (Table 1) into a three-dimensional network (Table 1). The crystal is further stabilized by weak C—H···π interactions (Table 1). π···π interactions were also observed with the distances of Cg1···Cg5 = 3.6228 (9) Å and Cg2···Cg4 = 3.6881 (9) Å (symmetry code : x, y, z in each case); Cg1, Cg2, Cg3, Cg4 and Cg5 are the centroids of the C1A–C6A, C8A–C13A, C15A–C20A, C1B–C6B and C8B–C13B benzene rings, respectively.

Experimental

The title compound was synthesized by adding 2,4-dihydroxybenzaldehyde (0.552 g, 4 mmol) to a solution of o-phenylenediamine (0.216 g, 2 mmol) in ethanol (20 ml). The mixture was refluxed with stirring for half an hour. The resultant yellow solution was filtered. Yellow single crystals of the title compound suitable for x-ray structure determination were recrystallized from ethanol by slow evaporation of the solvent at room temperature over several days.

Refinement

Hydroxyl and imine H atoms were located from the difference map and refined riding on the parent atoms with refinement of the isotropic thermal parameters. The remaining H atoms were placed in calculated positions with d(C—H) = 0.93 Å, Uiso=1.2Ueq(C) for aromatic, CH, 0.96 Å, Uiso = 1.5Ueq(C) for CH3 atoms A rotating group model was used for the methyl groups.

Figures

Fig. 1.
The asymmetric unit of (I), showing 50% probability displacement ellipsoids and the atomic numbering. Intramolecular O—H···N, N—H···O and N—H···N hydrogen ...
Fig. 2.
The crystal packing of (I), viewed along the a axis, showing the molecular chains along the b axis. Hydrogen bonds are drawn as dashed lines.

Crystal data

C20H16N2O4·CH4OZ = 4
Mr = 380.39F000 = 800
Triclinic, P1Dx = 1.383 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 8.3672 (2) ÅCell parameters from 10651 reflections
b = 11.0813 (2) Åθ = 1.0–30.0º
c = 20.3217 (3) ŵ = 0.10 mm1
α = 89.313 (1)ºT = 100.0 (1) K
β = 80.309 (1)ºBlock, yellow
γ = 79.641 (1)º0.50 × 0.34 × 0.17 mm
V = 1826.73 (6) Å3

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer10651 independent reflections
Radiation source: fine-focus sealed tube7203 reflections with I > 2σ(I)'
Monochromator: graphiteRint = 0.034
Detector resolution: 8.33 pixels mm-1θmax = 30.0º
T = 100.0(1) Kθmin = 1.0º
ω scansh = −11→10
Absorption correction: multi-scan(SADABS; Bruker, 2005)k = −15→15
Tmin = 0.952, Tmax = 0.984l = −28→28
42593 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.056H-atom parameters constrained
wR(F2) = 0.162  w = 1/[σ2(Fo2) + (0.0788P)2 + 0.3402P] where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
10651 reflectionsΔρmax = 0.44 e Å3
515 parametersΔρmin = −0.34 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.
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)

xyzUiso*/Ueq
O1A0.38240 (14)1.21218 (9)0.37963 (5)0.0269 (3)
H1OA0.32311.18620.41970.055 (6)*
O2A0.70037 (13)0.81358 (9)0.39164 (5)0.0243 (2)
O3A0.83682 (14)0.59449 (9)0.48780 (5)0.0268 (3)
H3OA0.89480.59570.44310.054 (6)*
O4A0.49475 (14)0.34820 (10)0.60844 (5)0.0272 (3)
H4OA0.44850.29030.60310.061 (7)*
N1A0.94132 (15)0.74067 (10)0.29384 (6)0.0193 (3)
H1NA0.87390.72700.33290.042 (5)*
N2A0.97260 (16)0.52908 (11)0.36228 (6)0.0211 (3)
C1A0.73415 (19)1.05359 (13)0.26751 (7)0.0220 (3)
H1A0.79911.06780.22730.026*
C2A0.60758 (19)1.14282 (13)0.29478 (7)0.0231 (3)
H2A0.58701.21750.27360.028*
C3A0.50713 (19)1.12139 (12)0.35571 (7)0.0215 (3)
C4A0.53930 (19)1.01151 (12)0.38853 (7)0.0213 (3)
H4A0.47400.99960.42900.026*
C5A0.66928 (18)0.91814 (12)0.36127 (7)0.0201 (3)
C6A0.76932 (18)0.93925 (12)0.29904 (7)0.0191 (3)
C7A0.90059 (18)0.84951 (12)0.26841 (7)0.0198 (3)
H7A0.96180.86790.22820.024*
C8A1.06914 (18)0.64458 (12)0.26672 (7)0.0191 (3)
C9A1.17540 (19)0.65455 (13)0.20737 (7)0.0220 (3)
H9A1.16530.72740.18400.026*
C10A1.29635 (19)0.55566 (14)0.18314 (8)0.0251 (3)
H10A1.36680.56200.14320.030*
C11A1.31301 (19)0.44739 (14)0.21809 (8)0.0260 (3)
H11A1.39520.38150.20170.031*
C12A1.20798 (19)0.43678 (13)0.27732 (8)0.0250 (3)
H12A1.22050.36400.30070.030*
C13A1.08334 (18)0.53462 (13)0.30223 (7)0.0204 (3)
C14A0.90878 (19)0.43132 (13)0.37372 (7)0.0221 (3)
H14A0.93460.37000.34080.026*
C15A0.80086 (19)0.41174 (12)0.43391 (7)0.0206 (3)
C16A0.76986 (19)0.49236 (12)0.49003 (7)0.0206 (3)
C17A0.67009 (19)0.46828 (13)0.54807 (7)0.0223 (3)
H17A0.65350.52020.58510.027*
C18A0.59436 (19)0.36593 (13)0.55096 (7)0.0220 (3)
C19A0.6219 (2)0.28485 (13)0.49599 (7)0.0243 (3)
H19A0.57230.21590.49830.029*
C20A0.72290 (19)0.30880 (13)0.43892 (7)0.0241 (3)
H20A0.74050.25550.40240.029*
O1B1.06277 (14)0.29566 (9)0.12539 (5)0.0263 (2)
H1OB1.12640.31110.08130.060 (7)*
O2B0.78690 (13)0.70842 (9)0.11637 (5)0.0246 (2)
O3B0.65725 (14)0.90440 (9)0.01575 (5)0.0263 (2)
H3OB0.58660.91580.05750.050 (6)*
O4B1.01686 (14)1.13045 (10)−0.11108 (5)0.0269 (2)
H4OB1.07771.1886−0.11380.065 (7)*
N1B0.53881 (15)0.78591 (10)0.21044 (6)0.0188 (3)
H1NB0.60500.79650.17390.043 (6)*
N2B0.50773 (16)0.98985 (11)0.13603 (6)0.0212 (3)
C1B0.72248 (19)0.46765 (13)0.23763 (7)0.0218 (3)
H1B0.65400.45550.27730.026*
C2B0.84138 (19)0.37362 (13)0.21012 (7)0.0227 (3)
H2B0.85350.29780.23060.027*
C3B0.94691 (19)0.39181 (12)0.14999 (7)0.0209 (3)
C4B0.92878 (19)0.50368 (13)0.11862 (7)0.0218 (3)
H4B0.99830.51360.07890.026*
C5B0.80678 (18)0.60236 (12)0.14599 (7)0.0195 (3)
C6B0.70035 (18)0.58425 (12)0.20722 (7)0.0189 (3)
C7B0.57163 (18)0.67648 (12)0.23642 (7)0.0191 (3)
H7B0.50620.65980.27600.023*
C8B0.40985 (18)0.88345 (12)0.23481 (7)0.0186 (3)
C9B0.30337 (19)0.87881 (13)0.29475 (7)0.0223 (3)
H9B0.31520.80920.32080.027*
C10B0.17954 (19)0.97810 (14)0.31555 (8)0.0249 (3)
H10B0.10860.97540.35580.030*
C11B0.16100 (19)1.08150 (14)0.27664 (8)0.0264 (3)
H11B0.07661.14740.29060.032*
C12B0.26700 (19)1.08732 (13)0.21731 (8)0.0245 (3)
H12B0.25331.15700.19140.029*
C13B0.39474 (19)0.98924 (13)0.19586 (7)0.0204 (3)
C14B0.56811 (19)1.08790 (13)0.12067 (7)0.0222 (3)
H14B0.53721.15440.15040.027*
C15B0.68020 (19)1.09985 (12)0.06030 (7)0.0212 (3)
C16B0.72244 (19)1.00770 (12)0.00920 (7)0.0211 (3)
C17B0.83261 (19)1.02095 (13)−0.04789 (7)0.0225 (3)
H17B0.85790.9607−0.08140.027*
C18B0.90569 (19)1.12444 (13)−0.05529 (7)0.0222 (3)
C19B0.8645 (2)1.21803 (13)−0.00595 (7)0.0253 (3)
H19B0.91141.2883−0.01150.030*
C20B0.7541 (2)1.20413 (13)0.05044 (7)0.0255 (3)
H20B0.72751.26580.08320.031*
O5A0.78442 (15)0.63854 (10)−0.01097 (6)0.0355 (3)
H5OA0.78190.67560.02500.053*
C21A0.6263 (3)0.6108 (3)−0.00516 (12)0.0693 (8)
H21A0.54580.68360.00740.104*
H21B0.61280.54980.02830.104*
H21C0.61160.5797−0.04720.104*
O5B0.77865 (16)0.87056 (10)0.50980 (6)0.0370 (3)
H5OB0.73810.83990.47610.055*
C21B0.9533 (3)0.84547 (17)0.50003 (11)0.0475 (5)
H21D0.99150.75840.49660.071*
H21E0.99030.87800.53720.071*
H21F0.99640.88310.45970.071*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O1A0.0347 (7)0.0192 (5)0.0245 (6)0.0013 (5)−0.0056 (5)0.0008 (4)
O2A0.0273 (6)0.0196 (5)0.0238 (5)−0.0020 (4)−0.0007 (5)0.0079 (4)
O3A0.0374 (7)0.0182 (5)0.0266 (6)−0.0113 (5)−0.0032 (5)−0.0006 (4)
O4A0.0351 (7)0.0275 (6)0.0202 (5)−0.0114 (5)−0.0025 (5)0.0051 (4)
N1A0.0202 (7)0.0189 (6)0.0191 (6)−0.0048 (5)−0.0029 (5)0.0028 (4)
N2A0.0232 (7)0.0197 (6)0.0207 (6)−0.0045 (5)−0.0039 (5)0.0032 (5)
C1A0.0274 (8)0.0213 (7)0.0196 (7)−0.0087 (6)−0.0065 (6)0.0048 (5)
C2A0.0318 (9)0.0162 (6)0.0238 (7)−0.0063 (6)−0.0101 (7)0.0057 (5)
C3A0.0253 (8)0.0174 (6)0.0233 (7)−0.0037 (6)−0.0082 (6)−0.0016 (5)
C4A0.0250 (8)0.0200 (7)0.0193 (7)−0.0052 (6)−0.0033 (6)0.0028 (5)
C5A0.0227 (8)0.0182 (6)0.0214 (7)−0.0067 (6)−0.0063 (6)0.0039 (5)
C6A0.0202 (8)0.0182 (6)0.0209 (7)−0.0061 (6)−0.0067 (6)0.0034 (5)
C7A0.0225 (8)0.0217 (7)0.0177 (7)−0.0086 (6)−0.0054 (6)0.0030 (5)
C8A0.0173 (7)0.0204 (6)0.0204 (7)−0.0048 (5)−0.0042 (6)−0.0001 (5)
C9A0.0233 (8)0.0238 (7)0.0207 (7)−0.0075 (6)−0.0060 (6)0.0028 (5)
C10A0.0214 (8)0.0304 (8)0.0236 (7)−0.0080 (6)−0.0007 (6)−0.0029 (6)
C11A0.0201 (8)0.0247 (7)0.0321 (8)−0.0020 (6)−0.0029 (7)−0.0064 (6)
C12A0.0246 (8)0.0210 (7)0.0299 (8)−0.0041 (6)−0.0061 (7)−0.0003 (6)
C13A0.0227 (8)0.0206 (7)0.0194 (7)−0.0061 (6)−0.0054 (6)0.0018 (5)
C14A0.0253 (8)0.0198 (6)0.0222 (7)−0.0046 (6)−0.0065 (6)0.0012 (5)
C15A0.0244 (8)0.0181 (6)0.0200 (7)−0.0053 (6)−0.0043 (6)0.0023 (5)
C16A0.0239 (8)0.0169 (6)0.0228 (7)−0.0051 (6)−0.0076 (6)0.0036 (5)
C17A0.0284 (9)0.0194 (6)0.0202 (7)−0.0041 (6)−0.0069 (6)0.0008 (5)
C18A0.0244 (8)0.0218 (7)0.0198 (7)−0.0037 (6)−0.0049 (6)0.0056 (5)
C19A0.0290 (9)0.0210 (7)0.0246 (8)−0.0096 (6)−0.0042 (6)0.0033 (6)
C20A0.0292 (9)0.0208 (7)0.0235 (7)−0.0077 (6)−0.0038 (6)−0.0017 (6)
O1B0.0326 (7)0.0182 (5)0.0253 (6)0.0023 (4)−0.0047 (5)0.0008 (4)
O2B0.0270 (6)0.0182 (5)0.0257 (5)−0.0024 (4)0.0011 (5)0.0069 (4)
O3B0.0342 (7)0.0198 (5)0.0261 (6)−0.0106 (5)−0.0024 (5)−0.0001 (4)
O4B0.0331 (7)0.0283 (6)0.0203 (5)−0.0107 (5)−0.0024 (5)0.0052 (4)
N1B0.0196 (6)0.0179 (5)0.0188 (6)−0.0040 (5)−0.0019 (5)0.0013 (4)
N2B0.0234 (7)0.0198 (6)0.0206 (6)−0.0041 (5)−0.0040 (5)0.0029 (5)
C1B0.0254 (8)0.0227 (7)0.0191 (7)−0.0080 (6)−0.0049 (6)0.0060 (5)
C2B0.0290 (9)0.0174 (6)0.0234 (7)−0.0065 (6)−0.0072 (6)0.0059 (5)
C3B0.0241 (8)0.0187 (6)0.0209 (7)−0.0030 (6)−0.0077 (6)0.0000 (5)
C4B0.0235 (8)0.0208 (7)0.0203 (7)−0.0038 (6)−0.0018 (6)0.0029 (5)
C5B0.0209 (8)0.0178 (6)0.0210 (7)−0.0061 (6)−0.0042 (6)0.0043 (5)
C6B0.0196 (8)0.0185 (6)0.0201 (7)−0.0051 (6)−0.0059 (6)0.0027 (5)
C7B0.0208 (8)0.0219 (7)0.0163 (6)−0.0076 (6)−0.0040 (6)0.0031 (5)
C8B0.0170 (7)0.0192 (6)0.0207 (7)−0.0042 (5)−0.0048 (6)−0.0014 (5)
C9B0.0227 (8)0.0240 (7)0.0214 (7)−0.0079 (6)−0.0034 (6)0.0012 (5)
C10B0.0211 (8)0.0316 (8)0.0222 (7)−0.0079 (6)−0.0004 (6)−0.0036 (6)
C11B0.0196 (8)0.0255 (7)0.0335 (8)−0.0029 (6)−0.0036 (7)−0.0063 (6)
C12B0.0261 (8)0.0194 (7)0.0293 (8)−0.0042 (6)−0.0080 (7)0.0013 (6)
C13B0.0218 (8)0.0202 (6)0.0207 (7)−0.0056 (6)−0.0057 (6)−0.0003 (5)
C14B0.0262 (8)0.0197 (7)0.0213 (7)−0.0041 (6)−0.0063 (6)0.0003 (5)
C15B0.0255 (8)0.0188 (6)0.0206 (7)−0.0048 (6)−0.0074 (6)0.0024 (5)
C16B0.0252 (8)0.0184 (6)0.0222 (7)−0.0060 (6)−0.0091 (6)0.0042 (5)
C17B0.0280 (9)0.0200 (7)0.0202 (7)−0.0042 (6)−0.0063 (6)0.0004 (5)
C18B0.0246 (8)0.0244 (7)0.0187 (7)−0.0059 (6)−0.0062 (6)0.0066 (5)
C19B0.0315 (9)0.0204 (7)0.0262 (8)−0.0095 (6)−0.0061 (7)0.0037 (6)
C20B0.0323 (9)0.0221 (7)0.0234 (8)−0.0085 (6)−0.0045 (7)0.0005 (6)
O5A0.0446 (8)0.0320 (6)0.0259 (6)−0.0036 (5)0.0020 (5)−0.0061 (5)
C21A0.0710 (18)0.0941 (19)0.0535 (14)−0.0471 (15)−0.0052 (12)−0.0218 (13)
O5B0.0476 (8)0.0312 (6)0.0264 (6)0.0059 (6)−0.0035 (6)−0.0034 (5)
C21B0.0521 (14)0.0349 (10)0.0598 (13)−0.0127 (9)−0.0163 (11)0.0007 (9)

Geometric parameters (Å, °)

O1A—C3A1.3420 (17)O4B—C18B1.3493 (18)
O1A—H1OA0.9500O4B—H4OB0.8863
O2A—C5A1.3113 (16)N1B—C7B1.3183 (17)
O3A—C16A1.3473 (16)N1B—C8B1.4112 (18)
O3A—H3OA0.9560N1B—H1NB0.8691
O4A—C18A1.3503 (18)N2B—C14B1.2921 (18)
O4A—H4OA0.8240N2B—C13B1.4097 (19)
N1A—C7A1.3169 (17)C1B—C2B1.357 (2)
N1A—C8A1.4098 (18)C1B—C6B1.4209 (18)
N1A—H1NA0.9215C1B—H1B0.9300
N2A—C14A1.2934 (18)C2B—C3B1.417 (2)
N2A—C13A1.4105 (19)C2B—H2B0.9300
C1A—C2A1.358 (2)C3B—C4B1.3828 (19)
C1A—C6A1.4186 (19)C4B—C5B1.403 (2)
C1A—H1A0.9300C4B—H4B0.9300
C2A—C3A1.418 (2)C5B—C6B1.438 (2)
C2A—H2A0.9300C6B—C7B1.400 (2)
C3A—C4A1.3868 (19)C7B—H7B0.9300
C4A—C5A1.402 (2)C8B—C9B1.389 (2)
C4A—H4A0.9300C8B—C13B1.4053 (19)
C5A—C6A1.436 (2)C9B—C10B1.384 (2)
C6A—C7A1.405 (2)C9B—H9B0.9300
C7A—H7A0.9300C10B—C11B1.385 (2)
C8A—C9A1.389 (2)C10B—H10B0.9300
C8A—C13A1.4054 (19)C11B—C12B1.380 (2)
C9A—C10A1.383 (2)C11B—H11B0.9300
C9A—H9A0.9300C12B—C13B1.397 (2)
C10A—C11A1.384 (2)C12B—H12B0.9300
C10A—H10A0.9300C14B—C15B1.434 (2)
C11A—C12A1.383 (2)C14B—H14B0.9300
C11A—H11A0.9300C15B—C20B1.4028 (19)
C12A—C13A1.396 (2)C15B—C16B1.4206 (19)
C12A—H12A0.9300C16B—C17B1.379 (2)
C14A—C15A1.432 (2)C17B—C18B1.389 (2)
C14A—H14A0.9300C17B—H17B0.9300
C15A—C20A1.4069 (19)C18B—C19B1.407 (2)
C15A—C16A1.4169 (19)C19B—C20B1.371 (2)
C16A—C17A1.378 (2)C19B—H19B0.9300
C17A—C18A1.391 (2)C20B—H20B0.9300
C17A—H17A0.9300O5A—C21A1.398 (2)
C18A—C19A1.404 (2)O5A—H5OA0.8380
C19A—C20A1.368 (2)C21A—H21A0.9600
C19A—H19A0.9300C21A—H21B0.9600
C20A—H20A0.9300C21A—H21C0.9600
O1B—C3B1.3428 (17)O5B—C21B1.418 (2)
O1B—H1OB0.9923O5B—H5OB0.9079
O2B—C5B1.3106 (16)C21B—H21D0.9600
O3B—C16B1.3498 (16)C21B—H21E0.9600
O3B—H3OB0.9451C21B—H21F0.9600
C3A—O1A—H1OA108.9C2B—C1B—C6B121.45 (14)
C16A—O3A—H3OA104.7C2B—C1B—H1B119.3
C18A—O4A—H4OA109.0C6B—C1B—H1B119.3
C7A—N1A—C8A127.48 (13)C1B—C2B—C3B119.54 (13)
C7A—N1A—H1NA114.2C1B—C2B—H2B120.2
C8A—N1A—H1NA118.2C3B—C2B—H2B120.2
C14A—N2A—C13A118.47 (12)O1B—C3B—C4B122.39 (14)
C2A—C1A—C6A121.38 (14)O1B—C3B—C2B116.82 (12)
C2A—C1A—H1A119.3C4B—C3B—C2B120.78 (13)
C6A—C1A—H1A119.3C3B—C4B—C5B120.80 (14)
C1A—C2A—C3A119.60 (13)C3B—C4B—H4B119.6
C1A—C2A—H2A120.2C5B—C4B—H4B119.6
C3A—C2A—H2A120.2O2B—C5B—C4B121.44 (13)
O1A—C3A—C4A122.46 (14)O2B—C5B—C6B120.08 (13)
O1A—C3A—C2A116.87 (12)C4B—C5B—C6B118.46 (12)
C4A—C3A—C2A120.67 (13)C7B—C6B—C1B118.99 (13)
C3A—C4A—C5A120.66 (14)C7B—C6B—C5B122.01 (12)
C3A—C4A—H4A119.7C1B—C6B—C5B118.96 (13)
C5A—C4A—H4A119.7N1B—C7B—C6B123.07 (13)
O2A—C5A—C4A121.24 (13)N1B—C7B—H7B118.5
O2A—C5A—C6A120.17 (13)C6B—C7B—H7B118.5
C4A—C5A—C6A118.59 (12)C9B—C8B—C13B120.41 (13)
C7A—C6A—C1A119.15 (13)C9B—C8B—N1B122.93 (12)
C7A—C6A—C5A121.77 (12)C13B—C8B—N1B116.65 (13)
C1A—C6A—C5A119.08 (13)C10B—C9B—C8B119.76 (14)
N1A—C7A—C6A123.28 (13)C10B—C9B—H9B120.1
N1A—C7A—H7A118.4C8B—C9B—H9B120.1
C6A—C7A—H7A118.4C9B—C10B—C11B120.23 (15)
C9A—C8A—C13A120.45 (13)C9B—C10B—H10B119.9
C9A—C8A—N1A122.92 (12)C11B—C10B—H10B119.9
C13A—C8A—N1A116.61 (13)C12B—C11B—C10B120.40 (14)
C10A—C9A—C8A119.76 (13)C12B—C11B—H11B119.8
C10A—C9A—H9A120.1C10B—C11B—H11B119.8
C8A—C9A—H9A120.1C11B—C12B—C13B120.44 (14)
C9A—C10A—C11A120.34 (15)C11B—C12B—H12B119.8
C9A—C10A—H10A119.8C13B—C12B—H12B119.8
C11A—C10A—H10A119.8C12B—C13B—C8B118.71 (14)
C12A—C11A—C10A120.27 (14)C12B—C13B—N2B123.18 (13)
C12A—C11A—H11A119.9C8B—C13B—N2B118.09 (13)
C10A—C11A—H11A119.9N2B—C14B—C15B123.63 (13)
C11A—C12A—C13A120.43 (14)N2B—C14B—H14B118.2
C11A—C12A—H12A119.8C15B—C14B—H14B118.2
C13A—C12A—H12A119.8C20B—C15B—C16B117.67 (14)
C12A—C13A—C8A118.72 (14)C20B—C15B—C14B120.20 (13)
C12A—C13A—N2A122.94 (13)C16B—C15B—C14B122.12 (13)
C8A—C13A—N2A118.32 (13)O3B—C16B—C17B118.42 (12)
N2A—C14A—C15A124.04 (13)O3B—C16B—C15B120.78 (13)
N2A—C14A—H14A118.0C17B—C16B—C15B120.79 (13)
C15A—C14A—H14A118.0C16B—C17B—C18B119.86 (13)
C20A—C15A—C16A117.79 (13)C16B—C17B—H17B120.1
C20A—C15A—C14A119.92 (13)C18B—C17B—H17B120.1
C16A—C15A—C14A122.29 (13)O4B—C18B—C17B117.28 (13)
O3A—C16A—C17A118.50 (12)O4B—C18B—C19B122.12 (13)
O3A—C16A—C15A120.74 (13)C17B—C18B—C19B120.60 (14)
C17A—C16A—C15A120.76 (13)C20B—C19B—C18B118.98 (13)
C16A—C17A—C18A119.73 (13)C20B—C19B—H19B120.5
C16A—C17A—H17A120.1C18B—C19B—H19B120.5
C18A—C17A—H17A120.1C19B—C20B—C15B122.06 (13)
O4A—C18A—C17A117.35 (13)C19B—C20B—H20B119.0
O4A—C18A—C19A121.91 (13)C15B—C20B—H20B119.0
C17A—C18A—C19A120.74 (14)C21A—O5A—H5OA103.6
C20A—C19A—C18A119.01 (13)O5A—C21A—H21A109.5
C20A—C19A—H19A120.5O5A—C21A—H21B109.5
C18A—C19A—H19A120.5H21A—C21A—H21B109.5
C19A—C20A—C15A121.93 (13)O5A—C21A—H21C109.5
C19A—C20A—H20A119.0H21A—C21A—H21C109.5
C15A—C20A—H20A119.0H21B—C21A—H21C109.5
C3B—O1B—H1OB113.4C21B—O5B—H5OB112.5
C16B—O3B—H3OB103.5O5B—C21B—H21D109.5
C18B—O4B—H4OB118.9O5B—C21B—H21E109.5
C7B—N1B—C8B127.42 (13)H21D—C21B—H21E109.5
C7B—N1B—H1NB114.3O5B—C21B—H21F109.5
C8B—N1B—H1NB118.3H21D—C21B—H21F109.5
C14B—N2B—C13B118.92 (12)H21E—C21B—H21F109.5
C6A—C1A—C2A—C3A−0.6 (2)C6B—C1B—C2B—C3B0.4 (2)
C1A—C2A—C3A—O1A−178.94 (13)C1B—C2B—C3B—O1B179.61 (13)
C1A—C2A—C3A—C4A1.6 (2)C1B—C2B—C3B—C4B−0.8 (2)
O1A—C3A—C4A—C5A178.95 (12)O1B—C3B—C4B—C5B−179.67 (12)
C2A—C3A—C4A—C5A−1.6 (2)C2B—C3B—C4B—C5B0.8 (2)
C3A—C4A—C5A—O2A−179.61 (13)C3B—C4B—C5B—O2B−179.15 (13)
C3A—C4A—C5A—C6A0.6 (2)C3B—C4B—C5B—C6B−0.4 (2)
C2A—C1A—C6A—C7A179.34 (13)C2B—C1B—C6B—C7B177.55 (13)
C2A—C1A—C6A—C5A−0.4 (2)C2B—C1B—C6B—C5B0.0 (2)
O2A—C5A—C6A—C7A0.9 (2)O2B—C5B—C6B—C7B1.3 (2)
C4A—C5A—C6A—C7A−179.35 (13)C4B—C5B—C6B—C7B−177.51 (13)
O2A—C5A—C6A—C1A−179.39 (12)O2B—C5B—C6B—C1B178.79 (12)
C4A—C5A—C6A—C1A0.36 (19)C4B—C5B—C6B—C1B0.00 (19)
C8A—N1A—C7A—C6A179.33 (12)C8B—N1B—C7B—C6B178.07 (12)
C1A—C6A—C7A—N1A−179.54 (13)C1B—C6B—C7B—N1B−177.73 (13)
C5A—C6A—C7A—N1A0.2 (2)C5B—C6B—C7B—N1B−0.2 (2)
C7A—N1A—C8A—C9A1.4 (2)C7B—N1B—C8B—C9B4.9 (2)
C7A—N1A—C8A—C13A−177.32 (13)C7B—N1B—C8B—C13B−176.36 (13)
C13A—C8A—C9A—C10A−0.2 (2)C13B—C8B—C9B—C10B1.3 (2)
N1A—C8A—C9A—C10A−178.88 (12)N1B—C8B—C9B—C10B179.98 (13)
C8A—C9A—C10A—C11A−0.7 (2)C8B—C9B—C10B—C11B0.4 (2)
C9A—C10A—C11A—C12A0.5 (2)C9B—C10B—C11B—C12B−0.9 (2)
C10A—C11A—C12A—C13A0.5 (2)C10B—C11B—C12B—C13B−0.2 (2)
C11A—C12A—C13A—C8A−1.3 (2)C11B—C12B—C13B—C8B1.9 (2)
C11A—C12A—C13A—N2A179.96 (13)C11B—C12B—C13B—N2B−179.56 (13)
C9A—C8A—C13A—C12A1.2 (2)C9B—C8B—C13B—C12B−2.4 (2)
N1A—C8A—C13A—C12A179.95 (12)N1B—C8B—C13B—C12B178.80 (12)
C9A—C8A—C13A—N2A179.95 (12)C9B—C8B—C13B—N2B178.95 (12)
N1A—C8A—C13A—N2A−1.28 (18)N1B—C8B—C13B—N2B0.20 (18)
C14A—N2A—C13A—C12A−43.96 (19)C14B—N2B—C13B—C12B43.0 (2)
C14A—N2A—C13A—C8A137.33 (14)C14B—N2B—C13B—C8B−138.49 (14)
C13A—N2A—C14A—C15A177.04 (13)C13B—N2B—C14B—C15B−178.21 (13)
N2A—C14A—C15A—C20A172.92 (14)N2B—C14B—C15B—C20B−173.14 (14)
N2A—C14A—C15A—C16A−7.8 (2)N2B—C14B—C15B—C16B5.9 (2)
C20A—C15A—C16A—O3A−178.04 (13)C20B—C15B—C16B—O3B179.28 (13)
C14A—C15A—C16A—O3A2.7 (2)C14B—C15B—C16B—O3B0.2 (2)
C20A—C15A—C16A—C17A1.7 (2)C20B—C15B—C16B—C17B0.1 (2)
C14A—C15A—C16A—C17A−177.56 (13)C14B—C15B—C16B—C17B−178.99 (13)
O3A—C16A—C17A—C18A177.61 (13)O3B—C16B—C17B—C18B−178.07 (13)
C15A—C16A—C17A—C18A−2.2 (2)C15B—C16B—C17B—C18B1.1 (2)
C16A—C17A—C18A—O4A−178.44 (13)C16B—C17B—C18B—O4B177.70 (12)
C16A—C17A—C18A—C19A1.8 (2)C16B—C17B—C18B—C19B−2.0 (2)
O4A—C18A—C19A—C20A179.29 (13)O4B—C18B—C19B—C20B−178.04 (13)
C17A—C18A—C19A—C20A−0.9 (2)C17B—C18B—C19B—C20B1.7 (2)
C18A—C19A—C20A—C15A0.5 (2)C18B—C19B—C20B—C15B−0.4 (2)
C16A—C15A—C20A—C19A−0.9 (2)C16B—C15B—C20B—C19B−0.5 (2)
C14A—C15A—C20A—C19A178.42 (14)C14B—C15B—C20B—C19B178.67 (14)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1A—H1OA···O5Bi0.951.712.6610 (16)176
O3A—H3OA···N2A0.961.782.6637 (16)153
O4A—H4OA···O2Aii0.821.832.6330 (16)164
N1A—H1NA···O2A0.921.842.6021 (16)138
N1A—H1NA···N2A0.922.312.7063 (16)106
O1B—H1OB···O5Aiii0.991.642.6205 (16)170
O3B—H3OB···N2B0.941.772.6526 (16)154
O4B—H4OB···O2Biv0.891.742.6241 (16)174
N1B—H1NB···O2B0.871.882.6006 (16)139
N1B—H1NB···N2B0.872.322.7020 (16)107
O5A—H5OA···O2B0.841.912.7145 (16)162
O5A—H5OA···O3B0.842.582.9703 (15)110
O5B—H5OB···O2A0.911.832.7034 (16)160
C4A—H4A···O5Bi0.932.483.165 (2)131
C4B—H4B···O5Aiii0.932.483.1596 (19)130
C7A—H7A···O4Biv0.932.363.1691 (17)146
C7B—H7B···O4Aii0.932.353.1253 (17)141
C12B—H12B···O1Bv0.932.553.3603 (18)146
C21B—H21D···O3A0.962.443.134 (2)129
C21B—H21D···Cg3vi0.962.863.568 (2)132

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+1, −y+1, −z+1; (iii) −x+2, −y+1, −z; (iv) −x+2, −y+2, −z; (v) x−1, y+1, z; (vi) −x+2, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2499).

References

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