(E)-N-[(Anthracen-9-yl)methyl­idene]hydroxyl­amine

Sebhaoui, J.; El Bakri, Y.; Essassi, E.M.; Mague, J.T.

doi:10.1107/S2414314617006848

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 5| May 2017| x170684

https://doi.org/10.1107/S2414314617006848

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(E)-N-[(Anthracen-9-yl)methylidene]hydroxylamine

Jihad Sebhaoui,^a ^* Youness El Bakri,^a El Mokhtar Essassi ^a and Joel T. Mague ^b

^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

Edited by J. Simpson, University of Otago, New Zealand (Received 5 May 2017; accepted 7 May 2017; online 16 May 2017)

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

Oximes constitute the key structural motif in numerous drug scaffolds and bioactive compounds, including macrolide antibiotics (roxithromycin), antifungal agents (econazole), cytotoxic agents (Park 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 ), nucleophilic catalysis of oxime ligation (Dirksen et al., 2006 ) and palladium-catalysed amination of aromatic C—H bonds with oxime esters (Tan & Hartwig, 2010 ).

In 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)°.

Figure 1
The title molecule with labelling scheme and 50% probability displacement ellipsoids.

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].

Table 1
Hydrogen-bond geometry (Å, °)

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.

Figure 2
Packing viewed along the b-axis direction, with O—H⋯N hydrogen bonds and offset π-stacking interactions shown, respectively, as red and orange dashed lines.

Figure 3
Packing viewed along the a-axis direction, with O—H⋯N hydrogen bonds and offset π-stacking interactions shown, respectively, as red and orange dashed lines.

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 refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₅H₁₁NO
M_r	221.25
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	13.463 (3), 3.8694 (8), 20.377 (4)
β (°)	101.023 (3)
V (Å³)	1041.9 (4)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.09
Crystal size (mm)	0.38 × 0.26 × 0.06

Data collection
Diffractometer	Bruker SMART APEX CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2016 )
T_min, T_max	0.93, 0.99
No. of measured, independent and observed [I > 2σ(I)] reflections	18825, 2790, 2217
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.685

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.125, 1.04
No. of reflections	2790
No. of parameters	198
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.24
Computer programs: APEX3 and SAINT (Bruker, 2016), SHELXT (Sheldrick, 2015a ), SHELXL2014 (Sheldrick, 2015b ), DIAMOND (Brandenburg & Putz, 2012 ) and SHELXTL (Sheldrick, 2008 ).

Structural data

CCDC reference: 1548341

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314617006848/sj4111sup1.cif

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

checkCIF report

Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: 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).

(E)-N-[(Anthracen-9-yl)methylidene]hydroxylamine top

Crystal data top

C₁₅H₁₁NO	F(000) = 464
M_r = 221.25	D_x = 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

Data collection top

Bruker SMART APEX CCD diffractometer	2790 independent reflections
Radiation source: fine-focus sealed tube	2217 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
Detector resolution: 8.3333 pixels mm^-1	θ_max = 29.1°, θ_min = 1.5°
φ and ω scans	h = −18→18
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −5→5
T_min = 0.93, T_max = 0.99	l = −27→27
18825 measured reflections

Refinement top

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(F_o²) + (0.0909P)²] where P = (F_o² + 2F_c²)/3
2790 reflections	(Δ/σ)_max < 0.001
198 parameters	Δρ_max = 0.44 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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.

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