organic compounds
(E)-N-[(Anthracen-9-yl)methylidene]hydroxylamine
aLaboratoire de Chimie Organique Hétérocyclique, URAC 21, Pôle de Compétence Pharmacochimie, Av Ibn Battouta, BP 1014, Faculté des Sciences, Mohammed V University, Rabat, Morocco, and bDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
*Correspondence e-mail: sebhaoui.jihad@gmail.com
In the title compound, C15H11NO, the anthracene unit is slightly bowed. Inversion-related pairs of O—H⋯N hydrogen bonds form dimers that are stacked along the b-axis direction by offset π–π stacking interactions between the anthracene units.
Keywords: crystal structure; hydrogen bonds; π-stacking.
CCDC reference: 1548341
Structure description
et al., 2005) and anti-inflammatory derivatives (cloximate). They are also intermediates in the production of isoxazole derivatives by 1,3-dipolar cycloaddition (Tribak et al., 2017; Al Houari et al., 2008). It is noteworthy that these compounds are also used in several important synthetic reactions, including oxime-carbapalladacycle-catalysed Suzuki cross-coupling of aryl chlorides in water (Botella & Nájera, 2002), of oxime ligation (Dirksen et al., 2006) and palladium-catalysed amination of aromatic C—H bonds with oxime (Tan & Hartwig, 2010).
constitute the key structural motif in numerous drug scaffolds and bioactive compounds, including macrolide antibiotics (roxithromycin), antifungal agents (econazole), cytotoxic agents (ParkIn the title compound (Fig. 1), the anthracene moiety is slightly bowed, as indicated by the dihedral angles of 2.77 (4) and 2.13 (4)°, respectively, that the C2–C7 and C9–C14 rings make with the central ring. The hydroxylimino side chain is rotated out of the mean plane of the anthracene unit, as indicated by the C2—C1—C15—N1 torsion angle of −42.5 (1)° and C1—C15—N1—O1 torsion angle of −175.87 (8)°.
In the crystal, inversion-related pairs of O—H⋯N hydrogen bonds form dimers and generate R22(6) rings (Table 1). These dimers form parallel stacks along the b-axis direction through offset π–π-stacking interactions between the anthracene moieties (Figs. 2 and 3). The centroid–centroid distances between equivalent rings of adjacent anthracene ring systems are 3.869 (1) Å. The mean planes of the anthracene moieties are inclined by 24.43 (1)° to [010].
Synthesis and crystallization
A solution of 2.00 g (9.70 mmol) 9-anthraldehyde, 1.35 g) (19.39 mmol) hydroxylamine hydrochloride and 775.74 mg) (19.39 mmol) of sodium hydroxide in 30 ml of ethanol and 10 ml of water, was refluxed for 30 min. The mixture reaction was neutralized with a solution of HCl, and extracted with dichloromethane. The solvent was removed under reduced pressure and the residue was recrystallized from ethanol ethanol to afford the title compound as light-yellow plates.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1548341
https://doi.org/10.1107/S2414314617006848/sj4111sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617006848/sj4111Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314617006848/sj4111Isup3.cdx
Supporting information file. DOI: https://doi.org/10.1107/S2414314617006848/sj4111Isup4.cml
Data collection: APEX3 (Bruker, 2016); cell
SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).C15H11NO | F(000) = 464 |
Mr = 221.25 | Dx = 1.410 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 13.463 (3) Å | Cell parameters from 7044 reflections |
b = 3.8694 (8) Å | θ = 2.3–29.1° |
c = 20.377 (4) Å | µ = 0.09 mm−1 |
β = 101.023 (3)° | T = 100 K |
V = 1041.9 (4) Å3 | Plate, light yellow |
Z = 4 | 0.38 × 0.26 × 0.06 mm |
Bruker SMART APEX CCD diffractometer | 2790 independent reflections |
Radiation source: fine-focus sealed tube | 2217 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
Detector resolution: 8.3333 pixels mm-1 | θmax = 29.1°, θmin = 1.5° |
φ and ω scans | h = −18→18 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | k = −5→5 |
Tmin = 0.93, Tmax = 0.99 | l = −27→27 |
18825 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: difference Fourier map |
wR(F2) = 0.125 | All H-atom parameters refined |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0909P)2] where P = (Fo2 + 2Fc2)/3 |
2790 reflections | (Δ/σ)max < 0.001 |
198 parameters | Δρmax = 0.44 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
Experimental. The diffraction data were obtained from 3 sets of 400 frames, each of width 0.5° in ω, colllected at φ = 0.00, 90.00 and 180.00° and 2 sets of 800 frames, each of width 0.45° in φ, collected at ω = –30.00 and 210.00°. The scan time was 15 sec/frame. |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.54777 (5) | 0.21769 (19) | 0.45469 (4) | 0.0199 (2) | |
H1 | 0.5653 (11) | 0.309 (4) | 0.4989 (8) | 0.042 (4)* | |
N1 | 0.45330 (6) | 0.3719 (2) | 0.43123 (4) | 0.0168 (2) | |
C1 | 0.31053 (7) | 0.3734 (2) | 0.34044 (5) | 0.0140 (2) | |
C2 | 0.23196 (7) | 0.4734 (2) | 0.37368 (5) | 0.0138 (2) | |
C3 | 0.23542 (7) | 0.4212 (3) | 0.44355 (5) | 0.0164 (2) | |
H3 | 0.2936 (10) | 0.307 (3) | 0.4700 (6) | 0.024 (3)* | |
C4 | 0.15692 (7) | 0.5188 (3) | 0.47305 (5) | 0.0188 (2) | |
H4 | 0.1611 (10) | 0.475 (4) | 0.5242 (7) | 0.029 (3)* | |
C5 | 0.06890 (8) | 0.6760 (3) | 0.43518 (5) | 0.0194 (2) | |
H5 | 0.0123 (11) | 0.754 (3) | 0.4558 (7) | 0.029 (3)* | |
C6 | 0.06159 (7) | 0.7253 (2) | 0.36835 (5) | 0.0177 (2) | |
H6 | 0.0024 (10) | 0.828 (3) | 0.3405 (6) | 0.023 (3)* | |
C7 | 0.14162 (7) | 0.6253 (2) | 0.33526 (5) | 0.0148 (2) | |
C8 | 0.13267 (7) | 0.6712 (2) | 0.26652 (5) | 0.0159 (2) | |
H8 | 0.0719 (9) | 0.784 (3) | 0.2404 (6) | 0.019 (3)* | |
C9 | 0.20768 (7) | 0.5601 (2) | 0.23283 (5) | 0.0149 (2) | |
C10 | 0.19705 (7) | 0.6009 (3) | 0.16186 (5) | 0.0168 (2) | |
H10 | 0.1347 (11) | 0.712 (3) | 0.1382 (6) | 0.029 (3)* | |
C11 | 0.26954 (7) | 0.4857 (3) | 0.12932 (5) | 0.0190 (2) | |
H11 | 0.2620 (9) | 0.508 (4) | 0.0774 (6) | 0.028 (3)* | |
C12 | 0.35777 (8) | 0.3213 (3) | 0.16552 (5) | 0.0186 (2) | |
H12 | 0.4090 (10) | 0.228 (3) | 0.1414 (6) | 0.024 (3)* | |
C13 | 0.37252 (8) | 0.2879 (3) | 0.23316 (5) | 0.0166 (2) | |
H13 | 0.4333 (10) | 0.174 (3) | 0.2577 (6) | 0.025 (3)* | |
C14 | 0.29814 (7) | 0.4042 (2) | 0.26996 (5) | 0.0141 (2) | |
C15 | 0.40798 (7) | 0.2371 (3) | 0.37667 (5) | 0.0165 (2) | |
H15 | 0.4403 (9) | 0.043 (3) | 0.3571 (6) | 0.023 (3)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0135 (4) | 0.0277 (4) | 0.0173 (4) | 0.0058 (3) | −0.0002 (3) | −0.0001 (3) |
N1 | 0.0120 (4) | 0.0192 (4) | 0.0184 (4) | 0.0016 (3) | 0.0008 (3) | 0.0028 (3) |
C1 | 0.0129 (4) | 0.0131 (4) | 0.0154 (5) | −0.0015 (3) | 0.0010 (3) | −0.0007 (3) |
C2 | 0.0130 (4) | 0.0132 (4) | 0.0151 (5) | −0.0013 (3) | 0.0022 (3) | −0.0006 (3) |
C3 | 0.0149 (4) | 0.0182 (5) | 0.0153 (5) | −0.0016 (4) | 0.0014 (4) | 0.0000 (4) |
C4 | 0.0190 (5) | 0.0211 (5) | 0.0168 (5) | −0.0025 (4) | 0.0045 (4) | −0.0011 (4) |
C5 | 0.0178 (5) | 0.0197 (5) | 0.0219 (5) | 0.0001 (4) | 0.0070 (4) | −0.0032 (4) |
C6 | 0.0140 (5) | 0.0165 (5) | 0.0219 (5) | 0.0014 (4) | 0.0022 (4) | −0.0013 (4) |
C7 | 0.0138 (4) | 0.0128 (4) | 0.0176 (5) | −0.0014 (3) | 0.0026 (4) | −0.0012 (3) |
C8 | 0.0133 (4) | 0.0149 (4) | 0.0182 (5) | −0.0003 (4) | 0.0001 (4) | 0.0006 (4) |
C9 | 0.0144 (4) | 0.0136 (4) | 0.0159 (5) | −0.0028 (3) | 0.0013 (4) | −0.0001 (3) |
C10 | 0.0157 (5) | 0.0181 (5) | 0.0155 (5) | −0.0038 (4) | 0.0002 (4) | 0.0012 (4) |
C11 | 0.0206 (5) | 0.0207 (5) | 0.0157 (5) | −0.0056 (4) | 0.0034 (4) | −0.0008 (4) |
C12 | 0.0189 (5) | 0.0191 (5) | 0.0192 (5) | −0.0037 (4) | 0.0074 (4) | −0.0025 (4) |
C13 | 0.0141 (5) | 0.0164 (5) | 0.0192 (5) | −0.0015 (4) | 0.0030 (4) | −0.0006 (4) |
C14 | 0.0131 (4) | 0.0129 (4) | 0.0161 (5) | −0.0024 (3) | 0.0024 (4) | −0.0015 (3) |
C15 | 0.0157 (5) | 0.0168 (5) | 0.0169 (5) | 0.0015 (4) | 0.0029 (4) | 0.0006 (3) |
O1—N1 | 1.4036 (10) | C6—H6 | 0.971 (13) |
O1—H1 | 0.954 (15) | C7—C8 | 1.3940 (14) |
N1—C15 | 1.2733 (13) | C8—C9 | 1.3932 (14) |
C1—C2 | 1.4148 (12) | C8—H8 | 0.989 (12) |
C1—C14 | 1.4188 (13) | C9—C10 | 1.4344 (14) |
C1—C15 | 1.4745 (14) | C9—C14 | 1.4377 (14) |
C2—C3 | 1.4300 (13) | C10—C11 | 1.3561 (14) |
C2—C7 | 1.4399 (13) | C10—H10 | 0.984 (14) |
C3—C4 | 1.3652 (13) | C11—C12 | 1.4228 (15) |
C3—H3 | 0.968 (13) | C11—H11 | 1.047 (12) |
C4—C5 | 1.4214 (14) | C12—C13 | 1.3605 (15) |
C4—H4 | 1.047 (13) | C12—H12 | 0.988 (13) |
C5—C6 | 1.3598 (15) | C13—C14 | 1.4334 (13) |
C5—H5 | 0.985 (14) | C13—H13 | 0.980 (13) |
C6—C7 | 1.4294 (13) | C15—H15 | 0.988 (12) |
N1—O1—H1 | 102.1 (9) | C9—C8—H8 | 118.3 (7) |
C15—N1—O1 | 112.02 (8) | C7—C8—H8 | 120.0 (7) |
C2—C1—C14 | 120.51 (8) | C8—C9—C10 | 121.39 (9) |
C2—C1—C15 | 122.23 (8) | C8—C9—C14 | 119.40 (9) |
C14—C1—C15 | 117.26 (8) | C10—C9—C14 | 119.20 (9) |
C1—C2—C3 | 123.58 (8) | C11—C10—C9 | 120.96 (9) |
C1—C2—C7 | 118.85 (8) | C11—C10—H10 | 122.1 (7) |
C3—C2—C7 | 117.54 (8) | C9—C10—H10 | 116.9 (7) |
C4—C3—C2 | 121.25 (9) | C10—C11—C12 | 120.06 (9) |
C4—C3—H3 | 119.6 (7) | C10—C11—H11 | 121.8 (7) |
C2—C3—H3 | 119.2 (7) | C12—C11—H11 | 118.1 (7) |
C3—C4—C5 | 120.96 (9) | C13—C12—C11 | 120.89 (9) |
C3—C4—H4 | 119.6 (7) | C13—C12—H12 | 119.2 (8) |
C5—C4—H4 | 119.4 (7) | C11—C12—H12 | 119.9 (8) |
C6—C5—C4 | 119.80 (9) | C12—C13—C14 | 121.26 (9) |
C6—C5—H5 | 118.0 (8) | C12—C13—H13 | 120.4 (7) |
C4—C5—H5 | 122.2 (8) | C14—C13—H13 | 118.3 (7) |
C5—C6—C7 | 121.18 (9) | C1—C14—C13 | 122.99 (9) |
C5—C6—H6 | 122.5 (7) | C1—C14—C9 | 119.46 (8) |
C7—C6—H6 | 116.4 (7) | C13—C14—C9 | 117.55 (9) |
C8—C7—C6 | 120.76 (9) | N1—C15—C1 | 121.50 (9) |
C8—C7—C2 | 120.00 (8) | N1—C15—H15 | 119.2 (7) |
C6—C7—C2 | 119.24 (9) | C1—C15—H15 | 119.2 (7) |
C9—C8—C7 | 121.62 (9) | ||
C14—C1—C2—C3 | 174.19 (8) | C8—C9—C10—C11 | −178.66 (9) |
C15—C1—C2—C3 | −6.34 (14) | C14—C9—C10—C11 | 1.97 (14) |
C14—C1—C2—C7 | −3.51 (13) | C9—C10—C11—C12 | 0.02 (15) |
C15—C1—C2—C7 | 175.96 (8) | C10—C11—C12—C13 | −2.31 (15) |
C1—C2—C3—C4 | −179.17 (9) | C11—C12—C13—C14 | 2.53 (15) |
C7—C2—C3—C4 | −1.44 (14) | C2—C1—C14—C13 | −176.13 (8) |
C2—C3—C4—C5 | 0.00 (15) | C15—C1—C14—C13 | 4.38 (13) |
C3—C4—C5—C6 | 1.12 (15) | C2—C1—C14—C9 | 4.20 (14) |
C4—C5—C6—C7 | −0.72 (15) | C15—C1—C14—C9 | −175.29 (8) |
C5—C6—C7—C8 | 178.83 (9) | C12—C13—C14—C1 | 179.84 (9) |
C5—C6—C7—C2 | −0.75 (14) | C12—C13—C14—C9 | −0.49 (14) |
C1—C2—C7—C8 | 0.05 (13) | C8—C9—C14—C1 | −1.43 (14) |
C3—C2—C7—C8 | −177.79 (8) | C10—C9—C14—C1 | 177.96 (8) |
C1—C2—C7—C6 | 179.63 (8) | C8—C9—C14—C13 | 178.89 (8) |
C3—C2—C7—C6 | 1.79 (13) | C10—C9—C14—C13 | −1.72 (13) |
C6—C7—C8—C9 | −176.82 (8) | O1—N1—C15—C1 | −175.87 (8) |
C2—C7—C8—C9 | 2.75 (14) | C2—C1—C15—N1 | −42.53 (14) |
C7—C8—C9—C10 | 178.57 (8) | C14—C1—C15—N1 | 136.96 (10) |
C7—C8—C9—C14 | −2.05 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1i | 0.954 (15) | 1.937 (15) | 2.8175 (12) | 152.4 (13) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Acknowledgements
JTM thanks Tulane University for support of the Tulane Crystallography Laboratory.
References
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