N-[(E)-Anthracen-9-yl­methyl­idene]-3,4-dimethyl-1,2-oxazol-5-amine

Abdullah M Asiri; Abdulrahman O Al-Youbi; Salman A Khan; M Nawaz Tahir

doi:10.1107/S1600536811050471

. 2011 Nov 30;67(Pt 12):o3487. doi: 10.1107/S1600536811050471

N-[(E)-Anthracen-9-ylmethylidene]-3,4-dimethyl-1,2-oxazol-5-amine

Abdullah M Asiri ^a,^b, Abdulrahman O Al-Youbi ^a, Salman A Khan ^a, M Nawaz Tahir ^c,^*

PMCID: PMC3239111 PMID: 22199959

Abstract

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

C₂₀H₁₆N₂O
M _r = 300.35
Monoclinic,
a = 22.4919 (14) Å
b = 6.1666 (4) Å
c = 22.6801 (13) Å
β = 102.015 (2)°
V = 3076.8 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.32 × 0.24 × 0.22 mm

Data collection

Bruker KAPPA APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T _min = 0.975, T _max = 0.980
12925 measured reflections
3193 independent reflections
2381 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.130
S = 1.04
3193 reflections
210 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: 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.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811050471/fk2045sup1.cif

e-67-o3487-sup1.cif^{(25.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811050471/fk2045Isup2.hkl

e-67-o3487-Isup2.hkl^{(153.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811050471/fk2045Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯N1	0.93	2.20	2.840 (2)	125

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Acknowledgments

The authors would like to thank the Chemistry Department, King Abdulaziz University, Jeddah, Saudi Arabia, for providing research facilities.

supplementary crystallographic information

Comment

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].

Experimental

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.

Figures

Fig. 1. — View of the title compound with the atom numbering scheme. The thermal ellipsoids are drawn at the 50% probability level. H-atoms are shown as small spheres of arbitrary radii. The dotted lines represent the intra-molecular H-bonds.

Crystal data

C₂₀H₁₆N₂O	F(000) = 1264
M_r = 300.35	D_x = 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

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Data collection

Bruker KAPPA APEXII CCD diffractometer	3193 independent reflections
Radiation source: fine-focus sealed tube	2381 reflections with I > 2σ(I)
graphite	R_int = 0.028
Detector resolution: 8.10 pixels mm^-1	θ_max = 26.5°, θ_min = 1.9°
ω scans	h = −28→27
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	k = −7→7
T_min = 0.975, T_max = 0.980	l = −23→28
12925 measured reflections

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Refinement

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(F_o²) + (0.0637P)² + 1.2672P] where P = (F_o² + 2F_c²)/3
3193 reflections	(Δ/σ)_max < 0.001
210 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

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Special details

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.

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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²)

	x	y	z	U_iso*/U_eq
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*

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Atomic displacement parameters (Å²)

	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)

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Geometric parameters (Å, °)

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)

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Hydrogen-bond geometry (Å, °)

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

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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FK2045).

References

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Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.
Khuhawar, M. Y., Mughal, M. A. & Channar, A. H. (2004). Eur. Polymer J. 40, 805–809.
Pandeya, S. N., Sriram, D., Nath, G. & Clercq, E. De. (1999). Pharm. Acta Helv. 74, 11–17. [DOI] [PubMed]
Saxena, A. & Tandon, J. P. (1983). Cancer Lett. 19, 73–76. [DOI] [PubMed]
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Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811050471/fk2045sup1.cif

e-67-o3487-sup1.cif^{(25.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811050471/fk2045Isup2.hkl

e-67-o3487-Isup2.hkl^{(153.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811050471/fk2045Isup3.cml

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

[bb1] Asiri, A. M. & Khan, S. A. (2010). Molecules, 15, 6850–6858. [DOI] [PMC free article] [PubMed]

[bb2] Asiri, A. M., Khan, S. A. & Tahir, M. N. (2011a). Acta Cryst. E67, o2163. [DOI] [PMC free article] [PubMed]

[bb3] Asiri, A. M., Khan, S. A. & Tahir, M. N. (2011b). Acta Cryst. E67, o2305. [DOI] [PMC free article] [PubMed]

[bb4] Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.

[bb5] Bruker (2009). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.

[bb6] Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.

[bb7] Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.

[bb8] Khuhawar, M. Y., Mughal, M. A. & Channar, A. H. (2004). Eur. Polymer J. 40, 805–809.

[bb9] Pandeya, S. N., Sriram, D., Nath, G. & Clercq, E. De. (1999). Pharm. Acta Helv. 74, 11–17. [DOI] [PubMed]

[bb10] Saxena, A. & Tandon, J. P. (1983). Cancer Lett. 19, 73–76. [DOI] [PubMed]

[bb11] Sheldrick, G. M. (2004). SADABS University of Göttingen, Germany.

[bb12] Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]

[bb13] Spek, A. L. (2009). Acta Cryst. D65, 148–155. [DOI] [PMC free article] [PubMed]

PERMALINK

N-[(E)-Anthracen-9-ylmethylidene]-3,4-dimethyl-1,2-oxazol-5-amine

Abdullah M Asiri

Abdulrahman O Al-Youbi

Salman A Khan

M Nawaz Tahir

Abstract

Related literature

Experimental

Crystal data

Data collection

Refinement

Supplementary Material

Table 1. Hydrogen-bond geometry (Å, °).

Acknowledgments

supplementary crystallographic information

Comment

Experimental

Refinement

Figures

Fig. 1.

Crystal data

Data collection

Refinement

Special details

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²)

Atomic displacement parameters (Å²)

Geometric parameters (Å, °)

Hydrogen-bond geometry (Å, °)

Footnotes

References

Associated Data

Supplementary Materials

ACTIONS

PERMALINK

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Cite

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PERMALINK

N-[(E)-Anthracen-9-yl­methyl­idene]-3,4-dimethyl-1,2-oxazol-5-amine

Abdullah M Asiri

Abdulrahman O Al-Youbi

Salman A Khan

M Nawaz Tahir

Abstract

Related literature

Experimental

Crystal data

Data collection

Refinement

Supplementary Material

Table 1. Hydrogen-bond geometry (Å, °).

Acknowledgments

supplementary crystallographic information

Comment

Experimental

Refinement

Figures

Fig. 1.

Crystal data

Data collection

Refinement

Special details

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

Atomic displacement parameters (Å2)

Geometric parameters (Å, °)

Hydrogen-bond geometry (Å, °)

Footnotes

References

Associated Data

Supplementary Materials

ACTIONS

PERMALINK

RESOURCES

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N-[(E)-Anthracen-9-ylmethylidene]-3,4-dimethyl-1,2-oxazol-5-amine

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²)

Atomic displacement parameters (Å²)