organic compounds
N-[(E)-Anthracen-9-ylmethylidene]-3,4-dimethyl-1,2-oxazol-5-amine
aDepartment of Chemistry, Faculty of Science, King Abdulaziz University, Jeddah 21589, PO Box 80203, Saudi Arabia, bThe Center of Excellence for Advanced Materials Reesrch, King Abdulaziz University, Jeddah 21589, PO Box 80203, Saudi Arabia, and cUniversity of Sargodha, Department of Physics, Sargodha, Pakistan
*Correspondence e-mail: dmntahir_uos@yahoo.com
In the title compound, C20H16N2O, an intramolecular C—H⋯N forms an S(6) ring motif. In the crystal, the molecules are stacked with their anthracene ring planes in sheets along [100].
Related literature
For applications of compounds containing azomethine groups, see: Khuhawar et al. (2004). Schiff base compounds demonstrate antibacterial (Asiri & Khan, 2010), antitumor activity (Saxena & Tandon, 1983) and anti-HIV activity (Pandeya et al., 1999). For related structures, see: Asiri et al. (2011a,b). For graph-set notation, see: Bernstein et al. (1995).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2009); cell SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON.
Supporting information
https://doi.org/10.1107/S1600536811050471/fk2045sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811050471/fk2045Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536811050471/fk2045Isup3.cml
A mixture of anthracene-9-carbaldehyde (0.50 g, 2.4 mmol) and 5-amino-3,4-dimethylisoxazole (2.4 mmol) in ethanol (15 ml) was heated for 3 h. The progress of the reaction was monitored by TLC. The solid that separated from the cooled mixture was collected and recrystallized from a methanol:chloroform mixture (8:2) to give red prisms of (I).
Red solid: Yield: 82%, m.p. 419–420 K.
Aromatic H-atoms were positioned geometrically (C–H = 0.93Å) and refined as riding with Uiso(H) = 1.2Ueq(C); methyl H positions were derived from difference maps (HFIX 137) and refined with C–H = 0.96Å and Uiso(H) = 1.5Ueq(C)
Compounds containing azomethine groups (C═N) play a vital role in chemistry (Khuhawar et al., 2004). Schiff-base compounds have been used as fine chemicals and medical substrates such as intermediates for the various reactions and antibacterial (Asiri & Khan, 2010), antitumor activity (Saxena & Tandon, 1983) and anti-HIV activity (Pandeya et al., 1999). containing heterocyclic rings dramatically increase the biological activity. The of title compound (I), (Fig. 1) is being reported here.
Recently, we have reported the
of (II) i.e., 4-[(anthracen-9-ylmethylidene)amino]-1,5-dimethyl-2-phenyl-1H- pyrazol-3(2H)-one (Asiri et al., 2011a) and (III) i.e., N-[(E)-1,3-benzodioxol-5-ylmethylidene]-3,4-dimethyl-1,2-oxazol -5-amine (Asiri et al., 2011b) which contain the common moieties of (I).In (I), the anthracen rings A (C1–C6), B (C1/C6/C7/C8/C13/C14) and C (C8–C13) are planar with r. m. s. deviations of 0.0090, 0.0241 and 0.0063 Å, respectively. The dihedral angles A/B, A/C and B/C are 4.80 (11)°, 8.36 (11) ° and 3.90 (10) °, respectively. The 3,4-dimethyl-1,2 -oxazol-5-amine moiety D (N1/C16–C20/N2/O1) is also planar with r. m. s. deviation of 0.0061 Å. The dihedral angles A/D, B/D and C/D are 7.59 (10)°, 3.85 (10)° and 5.48 (10)°, respectively. Intra-molecular H-bonds of C—H···N and C—H···O type complete S(6) and S(5) ring motifs (Fig. 1)(Bernstein et al., 1995). The crystal packing shows the anthracen ring planes stacked in parallel sheets along [100].
For applications of compounds containing azomethine groups, see: Khuhawar et al. (2004). Schiff base compounds demonstrate antibacterial (Asiri & Khan, 2010), antitumor activity (Saxena & Tandon, 1983) and anti-HIV activity (Pandeya et al., 1999). For related structures, see: Asiri et al. (2011a,b). For graph-set notation, see: Bernstein et al. (1995).
Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).C20H16N2O | F(000) = 1264 |
Mr = 300.35 | Dx = 1.297 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 2381 reflections |
a = 22.4919 (14) Å | θ = 1.9–26.5° |
b = 6.1666 (4) Å | µ = 0.08 mm−1 |
c = 22.6801 (13) Å | T = 296 K |
β = 102.015 (2)° | Prism, red |
V = 3076.8 (3) Å3 | 0.32 × 0.24 × 0.22 mm |
Z = 8 |
Bruker KAPPA APEXII CCD diffractometer | 3193 independent reflections |
Radiation source: fine-focus sealed tube | 2381 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
Detector resolution: 8.10 pixels mm-1 | θmax = 26.5°, θmin = 1.9° |
ω scans | h = −28→27 |
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | k = −7→7 |
Tmin = 0.975, Tmax = 0.980 | l = −23→28 |
12925 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.044 | Hydrogen site location: geom and difmap |
wR(F2) = 0.130 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0637P)2 + 1.2672P] where P = (Fo2 + 2Fc2)/3 |
3193 reflections | (Δ/σ)max < 0.001 |
210 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
C20H16N2O | V = 3076.8 (3) Å3 |
Mr = 300.35 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 22.4919 (14) Å | µ = 0.08 mm−1 |
b = 6.1666 (4) Å | T = 296 K |
c = 22.6801 (13) Å | 0.32 × 0.24 × 0.22 mm |
β = 102.015 (2)° |
Bruker KAPPA APEXII CCD diffractometer | 3193 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | 2381 reflections with I > 2σ(I) |
Tmin = 0.975, Tmax = 0.980 | Rint = 0.028 |
12925 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.130 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.26 e Å−3 |
3193 reflections | Δρmin = −0.21 e Å−3 |
210 parameters |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
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 > σ(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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.09676 (5) | 0.50025 (19) | 0.05196 (5) | 0.0516 (4) | |
N1 | 0.10276 (6) | 0.2014 (2) | 0.11940 (6) | 0.0459 (4) | |
N2 | 0.05953 (7) | 0.6861 (3) | 0.03694 (7) | 0.0584 (5) | |
C1 | 0.16650 (6) | −0.1894 (3) | 0.17670 (6) | 0.0379 (4) | |
C2 | 0.12182 (7) | −0.1253 (3) | 0.20964 (7) | 0.0486 (5) | |
C3 | 0.10875 (8) | −0.2518 (3) | 0.25450 (8) | 0.0580 (6) | |
C4 | 0.13754 (8) | −0.4522 (3) | 0.26932 (8) | 0.0606 (7) | |
C5 | 0.17975 (8) | −0.5201 (3) | 0.23969 (8) | 0.0528 (6) | |
C6 | 0.19672 (7) | −0.3919 (3) | 0.19346 (7) | 0.0403 (5) | |
C7 | 0.24311 (7) | −0.4589 (3) | 0.16590 (7) | 0.0429 (5) | |
C8 | 0.26386 (7) | −0.3322 (3) | 0.12393 (6) | 0.0393 (5) | |
C9 | 0.31446 (7) | −0.3980 (3) | 0.09933 (7) | 0.0497 (6) | |
C10 | 0.33622 (8) | −0.2712 (3) | 0.06009 (8) | 0.0556 (6) | |
C11 | 0.30869 (8) | −0.0702 (3) | 0.04332 (8) | 0.0554 (6) | |
C12 | 0.25992 (7) | −0.0016 (3) | 0.06472 (7) | 0.0476 (5) | |
C13 | 0.23446 (6) | −0.1286 (2) | 0.10601 (6) | 0.0365 (5) | |
C14 | 0.18386 (6) | −0.0631 (2) | 0.13028 (6) | 0.0356 (4) | |
C15 | 0.15128 (7) | 0.1314 (2) | 0.10573 (7) | 0.0398 (5) | |
C16 | 0.07545 (7) | 0.3889 (3) | 0.09501 (7) | 0.0415 (5) | |
C17 | 0.02670 (7) | 0.4911 (3) | 0.10808 (7) | 0.0447 (5) | |
C18 | 0.01918 (7) | 0.6751 (3) | 0.07070 (8) | 0.0501 (6) | |
C19 | −0.02801 (9) | 0.8473 (3) | 0.06716 (10) | 0.0733 (8) | |
C20 | −0.00958 (9) | 0.4243 (4) | 0.15280 (9) | 0.0675 (7) | |
H2 | 0.10126 | 0.00518 | 0.20030 | 0.0584* | |
H3 | 0.08009 | −0.20426 | 0.27582 | 0.0696* | |
H4 | 0.12735 | −0.53754 | 0.29956 | 0.0728* | |
H5 | 0.19841 | −0.65363 | 0.24946 | 0.0633* | |
H7 | 0.26093 | −0.59368 | 0.17593 | 0.0515* | |
H9 | 0.33285 | −0.53105 | 0.11056 | 0.0596* | |
H10 | 0.36913 | −0.31682 | 0.04434 | 0.0667* | |
H11 | 0.32424 | 0.01809 | 0.01692 | 0.0666* | |
H12 | 0.24256 | 0.13187 | 0.05217 | 0.0571* | |
H15 | 0.16724 | 0.21079 | 0.07779 | 0.0478* | |
H19A | −0.02371 | 0.91685 | 0.10569 | 0.1099* | |
H19B | −0.06768 | 0.78325 | 0.05612 | 0.1099* | |
H19C | −0.02301 | 0.95261 | 0.03740 | 0.1099* | |
H20A | 0.00725 | 0.29388 | 0.17266 | 0.1013* | |
H20B | −0.05088 | 0.39842 | 0.13254 | 0.1013* | |
H20C | −0.00855 | 0.53733 | 0.18209 | 0.1013* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0536 (7) | 0.0504 (7) | 0.0565 (7) | 0.0142 (5) | 0.0243 (5) | 0.0109 (5) |
N1 | 0.0428 (7) | 0.0438 (8) | 0.0535 (8) | 0.0056 (6) | 0.0158 (6) | 0.0045 (6) |
N2 | 0.0621 (9) | 0.0510 (9) | 0.0640 (10) | 0.0189 (7) | 0.0177 (8) | 0.0137 (7) |
C1 | 0.0335 (7) | 0.0412 (8) | 0.0383 (8) | −0.0033 (6) | 0.0061 (6) | −0.0001 (6) |
C2 | 0.0451 (9) | 0.0550 (10) | 0.0495 (9) | 0.0033 (8) | 0.0184 (7) | 0.0062 (8) |
C3 | 0.0509 (10) | 0.0745 (13) | 0.0539 (10) | −0.0015 (9) | 0.0232 (8) | 0.0084 (9) |
C4 | 0.0559 (11) | 0.0746 (13) | 0.0533 (10) | −0.0048 (10) | 0.0157 (8) | 0.0243 (10) |
C5 | 0.0492 (10) | 0.0527 (10) | 0.0539 (10) | −0.0015 (8) | 0.0051 (8) | 0.0167 (8) |
C6 | 0.0380 (8) | 0.0401 (9) | 0.0403 (8) | −0.0045 (7) | 0.0022 (6) | 0.0036 (7) |
C7 | 0.0411 (8) | 0.0374 (8) | 0.0472 (9) | 0.0045 (7) | 0.0021 (7) | 0.0024 (7) |
C8 | 0.0360 (8) | 0.0410 (9) | 0.0394 (8) | 0.0027 (6) | 0.0043 (6) | −0.0051 (7) |
C9 | 0.0426 (9) | 0.0536 (10) | 0.0522 (10) | 0.0125 (8) | 0.0085 (7) | −0.0051 (8) |
C10 | 0.0421 (9) | 0.0734 (13) | 0.0548 (10) | 0.0113 (9) | 0.0180 (8) | −0.0067 (9) |
C11 | 0.0489 (10) | 0.0699 (12) | 0.0530 (10) | 0.0021 (9) | 0.0232 (8) | 0.0059 (9) |
C12 | 0.0455 (9) | 0.0513 (10) | 0.0489 (9) | 0.0067 (8) | 0.0168 (7) | 0.0078 (8) |
C13 | 0.0341 (8) | 0.0395 (9) | 0.0356 (7) | 0.0008 (6) | 0.0064 (6) | −0.0028 (6) |
C14 | 0.0329 (7) | 0.0372 (8) | 0.0368 (7) | 0.0000 (6) | 0.0076 (6) | −0.0010 (6) |
C15 | 0.0392 (8) | 0.0405 (9) | 0.0429 (8) | 0.0026 (7) | 0.0157 (6) | 0.0023 (7) |
C16 | 0.0407 (8) | 0.0419 (9) | 0.0437 (8) | 0.0021 (7) | 0.0132 (7) | 0.0006 (7) |
C17 | 0.0396 (8) | 0.0453 (9) | 0.0507 (9) | 0.0041 (7) | 0.0127 (7) | −0.0054 (7) |
C18 | 0.0442 (9) | 0.0495 (10) | 0.0553 (10) | 0.0090 (8) | 0.0077 (8) | −0.0045 (8) |
C19 | 0.0640 (13) | 0.0621 (13) | 0.0937 (16) | 0.0253 (10) | 0.0162 (11) | −0.0007 (11) |
C20 | 0.0554 (11) | 0.0771 (14) | 0.0791 (13) | 0.0055 (10) | 0.0347 (10) | −0.0032 (11) |
O1—N2 | 1.418 (2) | C14—C15 | 1.4545 (19) |
O1—C16 | 1.360 (2) | C16—C17 | 1.350 (2) |
N1—C15 | 1.271 (2) | C17—C18 | 1.405 (3) |
N1—C16 | 1.371 (2) | C17—C20 | 1.486 (3) |
N2—C18 | 1.305 (2) | C18—C19 | 1.492 (3) |
C1—C2 | 1.427 (2) | C2—H2 | 0.9300 |
C1—C6 | 1.435 (3) | C3—H3 | 0.9300 |
C1—C14 | 1.428 (2) | C4—H4 | 0.9300 |
C2—C3 | 1.362 (2) | C5—H5 | 0.9300 |
C3—C4 | 1.403 (3) | C7—H7 | 0.9300 |
C4—C5 | 1.339 (3) | C9—H9 | 0.9300 |
C5—C6 | 1.427 (2) | C10—H10 | 0.9300 |
C6—C7 | 1.386 (2) | C11—H11 | 0.9300 |
C7—C8 | 1.385 (2) | C12—H12 | 0.9300 |
C8—C9 | 1.427 (2) | C15—H15 | 0.9300 |
C8—C13 | 1.438 (2) | C19—H19A | 0.9600 |
C9—C10 | 1.351 (2) | C19—H19B | 0.9600 |
C10—C11 | 1.402 (3) | C19—H19C | 0.9600 |
C11—C12 | 1.356 (2) | C20—H20A | 0.9600 |
C12—C13 | 1.429 (2) | C20—H20B | 0.9600 |
C13—C14 | 1.4220 (19) | C20—H20C | 0.9600 |
N2—O1—C16 | 107.56 (12) | N2—C18—C19 | 120.35 (17) |
C15—N1—C16 | 121.58 (14) | C17—C18—C19 | 127.02 (16) |
O1—N2—C18 | 105.36 (15) | C1—C2—H2 | 119.00 |
C2—C1—C6 | 116.67 (14) | C3—C2—H2 | 119.00 |
C2—C1—C14 | 124.43 (15) | C2—C3—H3 | 119.00 |
C6—C1—C14 | 118.88 (13) | C4—C3—H3 | 119.00 |
C1—C2—C3 | 121.16 (16) | C3—C4—H4 | 120.00 |
C2—C3—C4 | 121.52 (17) | C5—C4—H4 | 120.00 |
C3—C4—C5 | 119.68 (17) | C4—C5—H5 | 119.00 |
C4—C5—C6 | 121.43 (17) | C6—C5—H5 | 119.00 |
C1—C6—C5 | 119.50 (15) | C6—C7—H7 | 119.00 |
C1—C6—C7 | 119.97 (15) | C8—C7—H7 | 119.00 |
C5—C6—C7 | 120.51 (16) | C8—C9—H9 | 119.00 |
C6—C7—C8 | 122.32 (17) | C10—C9—H9 | 119.00 |
C7—C8—C9 | 121.24 (16) | C9—C10—H10 | 120.00 |
C7—C8—C13 | 119.07 (14) | C11—C10—H10 | 120.00 |
C9—C8—C13 | 119.68 (14) | C10—C11—H11 | 119.00 |
C8—C9—C10 | 121.40 (17) | C12—C11—H11 | 119.00 |
C9—C10—C11 | 119.36 (17) | C11—C12—H12 | 119.00 |
C10—C11—C12 | 121.53 (17) | C13—C12—H12 | 119.00 |
C11—C12—C13 | 121.87 (16) | N1—C15—H15 | 117.00 |
C8—C13—C12 | 116.13 (13) | C14—C15—H15 | 117.00 |
C8—C13—C14 | 119.78 (12) | C18—C19—H19A | 109.00 |
C12—C13—C14 | 124.07 (12) | C18—C19—H19B | 109.00 |
C1—C14—C13 | 119.62 (12) | C18—C19—H19C | 109.00 |
C1—C14—C15 | 122.60 (13) | H19A—C19—H19B | 109.00 |
C13—C14—C15 | 117.78 (12) | H19A—C19—H19C | 109.00 |
N1—C15—C14 | 125.21 (14) | H19B—C19—H19C | 109.00 |
O1—C16—N1 | 121.36 (14) | C17—C20—H20A | 109.00 |
O1—C16—C17 | 110.22 (15) | C17—C20—H20B | 109.00 |
N1—C16—C17 | 128.42 (15) | C17—C20—H20C | 109.00 |
C16—C17—C18 | 104.22 (14) | H20A—C20—H20B | 109.00 |
C16—C17—C20 | 127.36 (17) | H20A—C20—H20C | 109.00 |
C18—C17—C20 | 128.41 (17) | H20B—C20—H20C | 109.00 |
N2—C18—C17 | 112.63 (16) | ||
C16—O1—N2—C18 | −0.22 (18) | C6—C7—C8—C13 | −3.1 (2) |
N2—O1—C16—N1 | −179.18 (14) | C7—C8—C9—C10 | −177.53 (16) |
N2—O1—C16—C17 | 0.46 (18) | C13—C8—C9—C10 | 1.1 (2) |
C16—N1—C15—C14 | 178.72 (14) | C7—C8—C13—C12 | 177.20 (14) |
C15—N1—C16—O1 | 4.6 (2) | C7—C8—C13—C14 | −1.6 (2) |
C15—N1—C16—C17 | −174.96 (17) | C9—C8—C13—C12 | −1.5 (2) |
O1—N2—C18—C17 | −0.09 (19) | C9—C8—C13—C14 | 179.74 (14) |
O1—N2—C18—C19 | 179.65 (15) | C8—C9—C10—C11 | 0.3 (3) |
C6—C1—C2—C3 | −0.2 (2) | C9—C10—C11—C12 | −1.3 (3) |
C14—C1—C2—C3 | −178.22 (15) | C10—C11—C12—C13 | 0.8 (3) |
C2—C1—C6—C5 | 2.0 (2) | C11—C12—C13—C8 | 0.5 (2) |
C2—C1—C6—C7 | −176.27 (15) | C11—C12—C13—C14 | 179.27 (15) |
C14—C1—C6—C5 | −179.86 (15) | C8—C13—C14—C1 | 6.3 (2) |
C14—C1—C6—C7 | 1.8 (2) | C8—C13—C14—C15 | −173.06 (13) |
C2—C1—C14—C13 | 171.60 (14) | C12—C13—C14—C1 | −172.43 (14) |
C2—C1—C14—C15 | −9.1 (2) | C12—C13—C14—C15 | 8.3 (2) |
C6—C1—C14—C13 | −6.3 (2) | C1—C14—C15—N1 | −4.8 (2) |
C6—C1—C14—C15 | 172.94 (14) | C13—C14—C15—N1 | 174.48 (14) |
C1—C2—C3—C4 | −1.5 (3) | O1—C16—C17—C18 | −0.49 (19) |
C2—C3—C4—C5 | 1.3 (3) | O1—C16—C17—C20 | −179.47 (17) |
C3—C4—C5—C6 | 0.6 (3) | N1—C16—C17—C18 | 179.11 (17) |
C4—C5—C6—C1 | −2.3 (3) | N1—C16—C17—C20 | 0.1 (3) |
C4—C5—C6—C7 | 176.03 (17) | C16—C17—C18—N2 | 0.4 (2) |
C1—C6—C7—C8 | 3.0 (2) | C16—C17—C18—C19 | −179.36 (18) |
C5—C6—C7—C8 | −175.34 (16) | C20—C17—C18—N2 | 179.32 (18) |
C6—C7—C8—C9 | 175.57 (15) | C20—C17—C18—C19 | −0.4 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···N1 | 0.93 | 2.20 | 2.840 (2) | 125 |
C15—H15···O1 | 0.93 | 2.38 | 2.7463 (18) | 103 |
Experimental details
Crystal data | |
Chemical formula | C20H16N2O |
Mr | 300.35 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 296 |
a, b, c (Å) | 22.4919 (14), 6.1666 (4), 22.6801 (13) |
β (°) | 102.015 (2) |
V (Å3) | 3076.8 (3) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.32 × 0.24 × 0.22 |
Data collection | |
Diffractometer | Bruker KAPPA APEXII CCD |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2004) |
Tmin, Tmax | 0.975, 0.980 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12925, 3193, 2381 |
Rint | 0.028 |
(sin θ/λ)max (Å−1) | 0.628 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.130, 1.04 |
No. of reflections | 3193 |
No. of parameters | 210 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.26, −0.21 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).
Acknowledgements
The authors would like to thank the Chemistry Department, King Abdulaziz University, Jeddah, Saudi Arabia, for providing research facilities.
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Compounds containing azomethine groups (C═N) play a vital role in chemistry (Khuhawar et al., 2004). Schiff-base compounds have been used as fine chemicals and medical substrates such as intermediates for the various reactions and antibacterial (Asiri & Khan, 2010), antitumor activity (Saxena & Tandon, 1983) and anti-HIV activity (Pandeya et al., 1999). Schiff bases containing heterocyclic rings dramatically increase the biological activity. The crystal structure of title compound (I), (Fig. 1) is being reported here.
Recently, we have reported the crystal structure of (II) i.e., 4-[(anthracen-9-ylmethylidene)amino]-1,5-dimethyl-2-phenyl-1H- pyrazol-3(2H)-one (Asiri et al., 2011a) and (III) i.e., N-[(E)-1,3-benzodioxol-5-ylmethylidene]-3,4-dimethyl-1,2-oxazol -5-amine (Asiri et al., 2011b) which contain the common moieties of (I).
In (I), the anthracen rings A (C1–C6), B (C1/C6/C7/C8/C13/C14) and C (C8–C13) are planar with r. m. s. deviations of 0.0090, 0.0241 and 0.0063 Å, respectively. The dihedral angles A/B, A/C and B/C are 4.80 (11)°, 8.36 (11) ° and 3.90 (10) °, respectively. The 3,4-dimethyl-1,2 -oxazol-5-amine moiety D (N1/C16–C20/N2/O1) is also planar with r. m. s. deviation of 0.0061 Å. The dihedral angles A/D, B/D and C/D are 7.59 (10)°, 3.85 (10)° and 5.48 (10)°, respectively. Intra-molecular H-bonds of C—H···N and C—H···O type complete S(6) and S(5) ring motifs (Fig. 1)(Bernstein et al., 1995). The crystal packing shows the anthracen ring planes stacked in parallel sheets along [100].