Crystal structures of (E)-1-naphthaldehyde oxime and (E)-phenanthrene-9-carbaldehyde oxime

Lasri, J.; Chulvi, K.; Eltayeb, N.E.

doi:10.1107/S2056989018002116

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Volume 74| Part 3| March 2018| Pages 332-336

https://doi.org/10.1107/S2056989018002116

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Crystal structures of (E)-1-naphthaldehyde oxime and (E)-phenanthrene-9-carbaldehyde oxime

Jamal Lasri,^a ^* Katherine Chulvi ^b ^* and Naser Eltaher Eltayeb ^a

^aDepartment of Chemistry, Rabigh College of Science and Arts, PO Box 344, King Abdulaziz University, Jeddah, Saudi Arabia, and ^bFB 1.3 Strukturanalytik, Bundesanstalt für Materialforschung und -prüfung (BAM), Berlin, Germany
^*Correspondence e-mail: jlasri@kau.edu.sa, katherine.chulvi-iborra@bam.de

Edited by G. Smith, Queensland University of Technology, Australia (Received 5 December 2017; accepted 4 February 2018; online 13 February 2018)

The aldoximes C₁₁H₉NO (I) and C₁₅H₁₁NO (II), synthesized in ca 90% yield, by treatment of 1-naphthaldehyde or phenanthrene-9-carbaldehyde, respectively, with hydroxylamine hydrochloride and sodium carbonate, have been characterized by IR, ¹H, ¹³C and DEPT-135 NMR spectroscopies, and also by single-crystal X-ray diffraction analysis. The molecules of (I) and (II) are conformationally similar, with the aldoxime substituent groups lying outside the planes of the naphthalene or phenanthrene rings, forming dihedral angles with them of 23.9 (4) and 27.9 (6)°, respectively. The crystal structures of both (I) and (II) are similar with a single intermolecular O—H⋯N hydrogen-bonding interaction, giving rise to the formation of one-dimensional polymeric chains extending along the 2₁ (b) screw axes in each.

Keywords: crystal structure; aromatic aldehydes; E-aldoximes; hydrogen bonding.

CCDC references: 1821856; 1821855

1. Chemical context

Oxime compounds have found many applications; for example in the medical field, they are used as antidotes for nerve agents (Kassa, 2002 ). Oximes are also used as intermediates in the industrial production of caprolactam, a precursor to Nylon 6 (Ritz et al., 2012 ). Oximes, HO—N=CR¹R², are also valuable and simple reagents containing the O—N=C moiety (Kukushkin & Pombeiro, 1999 ), which easily adds to nitrile ligands, to form a variety of nitrogen-containing products e.g. iminoacylated compounds (Kopylovich et al., 2009 ; Lasri et al., 2007 , 2008 ), amidines (Kopylovich et al., 2001 ), carboxamides (Kopylovich et al., 2002 ), phthalocyanines (Kopylovich et al., 2004 ), or 1,3,5-triazapentadiene species (Kopylovich et al., 2007 ). In this work, we report the synthesis and crystal structures of two aldoximes, viz. (E)-1-naphthaldehyde oxime (I) and (E)-phenanthrene-9-carbaldehyde oxime (II), by treatment of 1-naphthaldehyde or phenanthrene-9-carbaldehyde, respectively, with hydroxylamine hydrochloride and sodium carbonate.

2. Structural commentary

The title compounds (I) and (II) both crystallize in the non-centrosymmetric monoclinic space group P2₁ with Z = 2, with similar unit-cell parameters. The asymmetric unit contents for each are shown in Figs. 1 and 2. Compound (I) comprises a naphthalene unit functionalized with an aldoxime group at position 1. The naphthalene unit is, as expected, essentially planar but the plane containing the aldoxime atoms lies significantly out of the naphthalene plane [torsion angle N1—C11—C1—C2 = 23.6 (6)°] (Table 1). In the case of compound (II), the plane of the aldoxime group lies similarly out-of-plane with the phenanthrene ring system [comparative torsion angle N1—C11—C9—C10 = 27.6 (4)°], corresponding to dihedral angles between the two planes of 23.9 (4) and 27.9 (5)° for (I) and (II), respectively. The aldoxime group shows similar bond lengths for both structures: 1.395 (5) and 1.405 (3) Å for O1—N1, 1.273 (5) and 1.268 (3) Å for N1—C11, 1.461 (6) and 1.466 (4) Å for C1—C11 or C9—C11, for (I) and (II), respectively.

Table 1
Selected torsion angles (°) for the aldoxime groups in (I) and (II)

	Compound (I)	Compound (II)
C1/C9—C11—N1—O1	−175.5 (4)	−175.3 (2)
C2/C10—C1/C9—C11—N1	23.6 (6)	27.6 (4)
C8′—C1—C11—N1	−160.4 (4)	–
C8′—C9—C11—N1	–	−156.1 (2)

Figure 1
The molecular conformation and atom-numbering scheme for (I)

, with non-H atoms represented as 30% probability ellipsoids.

Figure 2
The molecular conformation and atom-numbering scheme for (II)

, with non-H atoms represented as 30% probability ellipsoids.

3. Supramolecular features

Similar intermolecular interactions are observed in the crystal structures of both (I) and (II). In each, molecules are linked through a single intermolecular O1—H⋯N1ⁱ hydrogen-bonding interaction [Tables 2 and 3 for (I) and (II), respectively]. These basic interactions are shown in Fig. 3, defining an oxime C(3) type II motif. It is well known that oximes are able to form different types of hydrogen-bonding motifs (Bruton et al., 2003 ). In the structures of both (I) and (II), the formation of a one-dimensional polymeric chain arrangement of molecules results, extending along the 2₁ (b) screw axes in each (Fig. 4).

Table 2
Hydrogen-bond geometry (Å, °) for (I)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1ⁱ	0.90 (6)	1.94 (6)	2.834 (5)	177 (6)
Symmetry code: (i) $[-x+2, y-{\script{1\over 2}}, -z+1]$ .

Table 3
Hydrogen-bond geometry (Å, °) for (II)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H⋯N1ⁱ	0.88 (3)	1.99 (3)	2.852 (3)	169 (3)
Symmetry code: (i) $[-x+1, y+{\script{1\over 2}}, -z+1]$ .

Figure 3
Intermolecular hydrogen-bonding associations for (I)

(left) and (II)

(right), shown as dashed lines. Non-associative H atoms have been omitted for clarity.

Figure 4
A packing diagram viewed along the a axis for (I)

(top) and (II)

(bottom), showing polymeric chain extensions.

4. Database survey

Many naphthalene-carbaldehyde oxime derivatives are present in the Cambridge Structural Database (Version 5.38; Groom et al. 2016 ) but no one crystal structure containing only an aldoxime group in position 1 of the naphthalene ring system has been reported. The most similar structures that can be found are LIVROY/LIVROY01 (Guo et al., 2008 ; Tarai & Baruah, 2016 ) with an additional hydroxyl group in position 2 and TIJPOS (Asaad et al., 2005 ) with a dimethylamino group in position 9. The most important difference between (I) and LIVROY/LIVROY01 are the two hydrogen bonds: one intramolecular O—H⋯N and another intermolecular O—H⋯O. As a result of the intramolecular hydrogen-bonding interaction, the aldoxime group in the latter compound is coplanar with the central naphthalene ring with a dihedral angle of 1.21° and torsion angles C1—C11—N1—O2 = 179.27, C3—C1—C11—N1 = −179.91 and C4—C1—C11—N1 = −0.76°. However, TIJPOS (Asaad et al., 2005), with just one type of intermolecular hydrogen bond, shows a rotation in the aldoxime group that is more dramatic than in (I) and (II) (Table 1), with a 40.35° deviation from the central naphthalene plane.

No examples of structures of phenanthrene-carbaldehyde oxime derivatives are present in the Cambridge Structural Database.

5. Synthesis and crystallization

The aldoximes (E)-1-naphthaldehyde oxime (I) and (E)-phenanthrene-9-carbaldehyde oxime (II) were synthesized, in ca 90% yield, by treatment of 1-naphthaldehyde or phenanthrene-9-carbaldehyde, respectively, with hydroxylamine hydrochloride and sodium carbonate in MeOH at room temperature. To a solution of hydroxylamine hydrochloride (41.6 mg, 0.60 mmol) in MeOH (10 ml) was added sodium carbonate (31.7 mg, 0.30 mmol). The reaction mixture was stirred at room temperature for 5 min. 1-Naphthaldehyde (85.0 mg, 0.54 mmol) or phenanthrene-9-carbaldehyde (112.2 mg, 0.54 mmol) was added and the reaction mixture was stirred at room temperature for 12 h. The precipitate formed was then filtered off and the filtrate was evaporated in vacuo. The crude residue was purified by column chromatography on silica (CHCl₃ as the eluent, 50 ml), followed by evaporation of the solvent in vacuo to give the pure aldoximes [(I), 84 mg, 90% yield and (II), 107 mg, 89% yield] (see reaction scheme).

Single crystals of the aldoximes (I) and (II) suitable for X-ray diffraction were obtained by slow evaporation of their 10 ml CHCl₃ solutions at room temperature. Compounds (I) and (II) were characterized by IR, ¹H, ¹³C and DEPT-135 NMR spectroscopies and also by single crystal X-ray diffraction analysis.

In the IR spectra of (I) and (II), the characteristic bands at wavenumbers 3389 and 3200 cm⁻¹ (O—H), and 1614 and 1607 cm-¹ (C=N), confirm the formation of the aldoximes (I) and (II), respectively. In the ¹H NMR spectra, we observed the absence of the signal of the aldehyde at ca 10 ppm and a new signal at ca 8.8 ppm due to the imine proton CH=N was detected. Moreover, in the ¹³C and DEPT-135 NMR spectra, the signal of the aldehyde at ca 190 ppm was not observed, and a new signal at ca 150 ppm due to the oxime carbon CH=NOH was detected, confirming the formation of the aldoximes (I) and (II).

(E)-1-naphthaldehyde oxime (I)

Yield: 90%. IR (cm⁻¹): 3389 (OH), 1614 (C=N). ¹H NMR (CDCl₃), δ: 7.53 (t, J_HH 7.5 Hz, 1H, CH_aromatic), 7.56 (t, J_HH 7.0 Hz, 1H, CH_aromatic), 7.61 (t, J_HH 7.0 Hz, 1H, CH_aromatic), 7.82 (d, J_HH 7.1 Hz, 1H, CH_aromatic), 7.93 (t, J_HH 8.1 Hz, 2H, CH_aromatic), 8.48 (d, J_HH 8.3 Hz, 1H, CH_aromatic), 8.87 (s, 1H, CH=N). ¹³C NMR (CDCl₃), δ: 124.2, 125.4, 126.2, 127.0, 127.1 (CH_aromatic), 128.0 (C_aromatic), 128.8, 130.6 (CH_aromatic), 130.8, 133.8 (C_aromatic), 150.0 (CH=N). DEPT-135 NMR (CDCl₃), δ: 124.2, 125.4, 126.2, 127.0, 127.1, 128.8, 130.6 (CH_aromatic), 150.0 (CH=N).

E-phenanthrene-9-carbaldehyde oxime (II)

Yield: 89%. IR (cm⁻¹): 3200 (OH), 1607 (C=N). ¹H NMR (CDCl₃), δ: 7.64 (t, J_HH 7.9 Hz, 1H, CH_aromatic), 7.68–7.75 (m, 3H, CH_aromatic), 7.94 (d, J_HH 7.9 Hz, 1H, CH_aromatic), 8.04 (s, 1H, CH_aromatic), 8.62 (d, J_HH 7.9 Hz, 1H, CH_aromatic), 8.70 (d, J_HH 8.2 Hz, 1H, CH_aromatic), 8.77 (d, J_HH 8.2 Hz, 1H, CH_aromatic), 8.85 (s, 1H, CH=N). ¹³C NMR (CDCl₃), δ: 122.6, 123.1, 125.4 (CH_aromatic), 126.8 (C_aromatic), 126.9, 127.0, 127.2, 127.9, 129.3 (CH_aromatic), 130.7, 131.0, 131.1 (C_aromatic), 150.8 (CH=N). DEPT-135 NMR (CDCl₃), δ: 122.6, 123.1, 125.4, 126.9, 127.0, 127.2, 127.9, 129.3 (CH_aromatic), 150.8 (CH=N).

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 4. All C-bound H atoms were located in difference-Fourier maps but were subsequently treated as riding with C—H = 0.93 Å and with U_iso(H) = 1.2U_eq(C). The H atoms of the OH groups were positioned with idealized geometry and were refined freely in both structures.

Table 4
Experimental details

	(I)	(II)
Crystal data
Chemical formula	C₁₁H₉NO	C₁₅H₁₁NO
M_r	171.19	221.25
Crystal system, space group	Monoclinic, P2₁	Monoclinic, P2₁
Temperature (K)	295	295
a, b, c (Å)	7.928 (5), 4.843 (3), 11.444 (7)	8.2397 (8), 4.9728 (5), 13.9332 (14)
β (°)	94.03 (5)	106.680 (7)
V (Å³)	438.3 (5)	546.88 (10)
Z	2	2
Radiation type	Mo Kα	Mo Kα
μ (mm⁻¹)	0.08	0.09
Crystal size (mm)	0.10 × 0.06 × 0.02	0.16 × 0.09 × 0.05

Data collection
Diffractometer	Bruker D8 Quest	Bruker D8 Quest
Absorption correction	Multi-scan (SADABS; Bruker, 2016 )	Multi-scan (SADABS; Bruker, 2016)
T_min, T_max	0.684, 0.745	0.698, 0.745
No. of measured, independent and observed [I > 2σ(I)] reflections	5762, 1570, 957	7330, 1988, 1509
R_int	0.100	0.053
(sin θ/λ)_max (Å⁻¹)	0.603	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.098, 1.06	0.040, 0.093, 1.04
No. of reflections	1570	1988
No. of parameters	122	159
No. of restraints	1	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.15	0.15, −0.15
Computer programs: APEX3 and SAINT (Bruker, 2016), SHELXT2014 (Sheldrick, 2015a ) and SHELXL2014 (Sheldrick, 2015b ).

Supporting information

CCDC references: 1821856; 1821855

Crystal structure: contains datablocks I, II, global. DOI: https://doi.org/10.1107/S2056989018002116/zs2397sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989018002116/zs2397Isup4.hkl

Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S2056989018002116/zs2397IIsup5.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989018002116/zs2397Isup4.cml

Supporting information file. DOI: https://doi.org/10.1107/S2056989018002116/zs2397IIsup5.cml

checkCIF report

Computing details top

For both structures, data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: SHELXL2014 (Sheldrick, 2015b).

(E)-1-Naphthaldehyde oxime (I) top

Crystal data top

C₁₁H₉NO	F(000) = 180
M_r = 171.19	D_x = 1.297 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 7.928 (5) Å	Cell parameters from 1367 reflections
b = 4.843 (3) Å	θ = 2.6–22.6°
c = 11.444 (7) Å	µ = 0.08 mm⁻¹
β = 94.03 (5)°	T = 295 K
V = 438.3 (5) Å³	Block, colourless
Z = 2	0.10 × 0.06 × 0.02 mm

Data collection top

Bruker D8 Quest diffractometer	957 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.100
Absorption correction: multi-scan (SADABS; Bruker, 2016)	θ_max = 25.4°, θ_min = 2.6°
T_min = 0.684, T_max = 0.745	h = −9→9
5762 measured reflections	k = −5→5
1570 independent reflections	l = −13→13

Refinement top

Refinement on F²	1 restraint
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.055	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.098	w = 1/[σ²(F_o²) + (0.0164P)² + 0.1408P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
1570 reflections	Δρ_max = 0.15 e Å⁻³
122 parameters	Δρ_min = −0.15 e Å⁻³

Special details top

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.

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

	x	y	z	U_iso*/U_eq
O1	0.8254 (4)	−0.0401 (7)	0.5056 (3)	0.0458 (9)
N1	0.8708 (5)	0.1715 (9)	0.4312 (3)	0.0418 (11)
C1	0.7559 (5)	0.4959 (10)	0.2895 (4)	0.0318 (12)
C2	0.8998 (6)	0.5156 (11)	0.2295 (4)	0.0452 (14)
H2	0.9903	0.3987	0.2494	0.054*
C3	0.9129 (7)	0.7072 (14)	0.1393 (5)	0.0569 (16)
H3	1.0128	0.7207	0.1017	0.068*
C4	0.7801 (7)	0.8737 (11)	0.1066 (4)	0.0499 (15)
H4	0.7888	0.9970	0.0450	0.060*
C4'	0.6296 (6)	0.8624 (10)	0.1645 (4)	0.0377 (12)
C5	0.4924 (6)	1.0383 (10)	0.1338 (4)	0.0468 (15)
H5	0.5009	1.1626	0.0726	0.056*
C6	0.3485 (7)	1.0323 (12)	0.1907 (5)	0.0570 (17)
H6	0.2585	1.1479	0.1677	0.068*
C7	0.3370 (6)	0.8491 (11)	0.2846 (4)	0.0478 (15)
H7	0.2393	0.8461	0.3250	0.057*
C8	0.4663 (5)	0.6760 (11)	0.3176 (4)	0.0387 (13)
H8	0.4557	0.5558	0.3800	0.046*
C8'	0.6172 (5)	0.6760 (10)	0.2582 (4)	0.0285 (11)
C11	0.7413 (6)	0.2826 (9)	0.3785 (4)	0.0350 (12)
H11	0.6343	0.2264	0.3972	0.042*
H1	0.922 (7)	−0.129 (13)	0.528 (5)	0.10 (2)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.041 (2)	0.044 (2)	0.051 (2)	0.008 (2)	−0.0047 (18)	0.008 (2)
N1	0.040 (2)	0.038 (3)	0.046 (3)	0.001 (2)	−0.005 (2)	−0.005 (2)
C1	0.033 (3)	0.029 (3)	0.033 (3)	−0.007 (3)	−0.002 (2)	−0.007 (3)
C2	0.035 (3)	0.054 (4)	0.048 (3)	−0.005 (3)	0.009 (2)	−0.014 (3)
C3	0.051 (3)	0.080 (5)	0.043 (3)	−0.018 (4)	0.021 (3)	−0.012 (4)
C4	0.064 (4)	0.051 (4)	0.036 (3)	−0.017 (3)	0.011 (3)	−0.005 (3)
C4'	0.046 (3)	0.037 (3)	0.029 (3)	−0.008 (3)	−0.003 (2)	−0.007 (3)
C5	0.060 (4)	0.037 (4)	0.041 (3)	−0.009 (3)	−0.011 (3)	0.008 (3)
C6	0.049 (3)	0.049 (4)	0.070 (4)	0.006 (3)	−0.013 (3)	0.008 (4)
C7	0.035 (3)	0.048 (4)	0.060 (4)	0.002 (3)	0.000 (3)	0.009 (3)
C8	0.036 (3)	0.039 (3)	0.040 (3)	0.002 (3)	−0.002 (2)	0.008 (3)
C8'	0.029 (2)	0.027 (3)	0.029 (3)	−0.004 (2)	−0.0016 (19)	−0.008 (3)
C11	0.032 (3)	0.029 (3)	0.044 (3)	0.002 (2)	0.003 (2)	−0.008 (3)

Geometric parameters (Å, º) top

O1—N1	1.395 (5)	C4'—C5	1.407 (6)
O1—H1	0.90 (6)	C4'—C8'	1.410 (6)
N1—C11	1.273 (5)	C5—C6	1.353 (6)
C1—C2	1.375 (6)	C5—H5	0.9300
C1—C8'	1.429 (6)	C6—C7	1.402 (7)
C1—C11	1.461 (6)	C6—H6	0.9300
C2—C3	1.397 (7)	C7—C8	1.357 (6)
C2—H2	0.9300	C7—H7	0.9300
C3—C4	1.358 (7)	C8—C8'	1.417 (5)
C3—H3	0.9300	C8—H8	0.9300
C4—C4'	1.406 (6)	C11—H11	0.9300
C4—H4	0.9300

N1—O1—H1	106 (4)	C6—C5—H5	119.0
C11—N1—O1	111.5 (4)	C4'—C5—H5	119.0
C2—C1—C8'	118.9 (4)	C5—C6—C7	119.0 (5)
C2—C1—C11	120.4 (5)	C5—C6—H6	120.5
C8'—C1—C11	120.6 (4)	C7—C6—H6	120.5
C1—C2—C3	121.5 (5)	C8—C7—C6	121.0 (5)
C1—C2—H2	119.3	C8—C7—H7	119.5
C3—C2—H2	119.3	C6—C7—H7	119.5
C4—C3—C2	120.1 (5)	C7—C8—C8'	120.9 (5)
C4—C3—H3	119.9	C7—C8—H8	119.5
C2—C3—H3	119.9	C8'—C8—H8	119.5
C3—C4—C4'	120.9 (5)	C4'—C8'—C8	118.1 (4)
C3—C4—H4	119.5	C4'—C8'—C1	119.2 (4)
C4'—C4—H4	119.5	C8—C8'—C1	122.7 (4)
C4—C4'—C5	121.7 (5)	N1—C11—C1	121.9 (4)
C4—C4'—C8'	119.3 (5)	N1—C11—H11	119.0
C5—C4'—C8'	118.9 (4)	C1—C11—H11	119.0
C6—C5—C4'	122.0 (5)

C8'—C1—C2—C3	0.1 (7)	C5—C4'—C8'—C8	−0.3 (6)
C11—C1—C2—C3	176.2 (5)	C4—C4'—C8'—C1	−2.1 (6)
C1—C2—C3—C4	−2.0 (8)	C5—C4'—C8'—C1	179.7 (4)
C2—C3—C4—C4'	1.8 (8)	C7—C8—C8'—C4'	0.5 (7)
C3—C4—C4'—C5	178.3 (5)	C7—C8—C8'—C1	−179.6 (4)
C3—C4—C4'—C8'	0.3 (7)	C2—C1—C8'—C4'	1.9 (6)
C4—C4'—C5—C6	−178.7 (5)	C11—C1—C8'—C4'	−174.2 (4)
C8'—C4'—C5—C6	−0.6 (7)	C2—C1—C8'—C8	−178.0 (4)
C4'—C5—C6—C7	1.3 (8)	C11—C1—C8'—C8	5.9 (6)
C5—C6—C7—C8	−1.2 (8)	O1—N1—C11—C1	−175.5 (4)
C6—C7—C8—C8'	0.2 (7)	C2—C1—C11—N1	23.6 (6)
C4—C4'—C8'—C8	177.8 (4)	C8'—C1—C11—N1	−160.4 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1ⁱ	0.90 (6)	1.94 (6)	2.834 (5)	177 (6)

Symmetry code: (i) −x+2, y−1/2, −z+1.

(E)-Phenanthrene-9-carbaldehyde oxime (II) top

Crystal data top

C₁₅H₁₁NO	F(000) = 232
M_r = 221.25	D_x = 1.344 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 8.2397 (8) Å	Cell parameters from 2141 reflections
b = 4.9728 (5) Å	θ = 2.6–24.9°
c = 13.9332 (14) Å	µ = 0.09 mm⁻¹
β = 106.680 (7)°	T = 295 K
V = 546.88 (10) Å³	Block, colourless
Z = 2	0.16 × 0.09 × 0.05 mm

Data collection top

Bruker D8 Quest diffractometer	1509 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.053
Absorption correction: multi-scan (SADABS; Bruker, 2016)	θ_max = 25.3°, θ_min = 2.6°
T_min = 0.698, T_max = 0.745	h = −9→9
7330 measured reflections	k = −5→5
1988 independent reflections	l = −16→16

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.040	w = 1/[σ²(F_o²) + (0.0478P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.093	(Δ/σ)_max < 0.001
S = 1.04	Δρ_max = 0.15 e Å⁻³
1988 reflections	Δρ_min = −0.15 e Å⁻³
159 parameters	Extinction correction: SHELXL2016 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.058 (11)

Special details top

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

	x	y	z	U_iso*/U_eq
O1	0.3294 (3)	1.0407 (5)	0.49418 (15)	0.0446 (6)
N1	0.4084 (3)	0.8293 (5)	0.55737 (16)	0.0371 (6)
C11	0.3086 (4)	0.7264 (5)	0.6016 (2)	0.0340 (7)
H11	0.197024	0.785637	0.585614	0.041*
C9	0.3660 (3)	0.5157 (6)	0.67732 (18)	0.0322 (7)
C10	0.5314 (4)	0.5027 (7)	0.7316 (2)	0.0366 (7)
H10	0.607395	0.622514	0.716727	0.044*
C10'	0.5935 (3)	0.3140 (6)	0.81023 (19)	0.0349 (7)
C1	0.7655 (4)	0.3096 (7)	0.8651 (2)	0.0472 (8)
H1	0.840812	0.427685	0.848577	0.057*
C2	0.8232 (4)	0.1335 (8)	0.9426 (2)	0.0510 (9)
H2	0.937339	0.131717	0.978623	0.061*
C3	0.7116 (4)	−0.0423 (7)	0.9676 (2)	0.0481 (9)
H3	0.751583	−0.162219	1.020293	0.058*
C4	0.5438 (4)	−0.0424 (6)	0.9159 (2)	0.0445 (8)
H4	0.470941	−0.162230	0.933886	0.053*
C4'	0.4792 (4)	0.1366 (6)	0.83561 (19)	0.0333 (7)
C5'	0.3013 (4)	0.1442 (6)	0.77844 (19)	0.0334 (7)
C5	0.1811 (4)	−0.0332 (6)	0.7975 (2)	0.0431 (8)
H5	0.215809	−0.156417	0.849626	0.052*
C6	0.0153 (4)	−0.0300 (7)	0.7419 (3)	0.0499 (9)
H6	−0.061247	−0.149898	0.756119	0.060*
C7	−0.0389 (4)	0.1524 (7)	0.6641 (2)	0.0499 (9)
H7	−0.151904	0.154288	0.626056	0.060*
C8	0.0728 (4)	0.3292 (7)	0.6429 (2)	0.0424 (8)
H8	0.034520	0.451063	0.590667	0.051*
C8'	0.2453 (3)	0.3306 (6)	0.69893 (19)	0.0317 (7)
H	0.413 (4)	1.109 (7)	0.475 (2)	0.061 (12)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0474 (13)	0.0426 (14)	0.0448 (12)	0.0035 (11)	0.0145 (10)	0.0153 (11)
N1	0.0446 (14)	0.0344 (14)	0.0343 (13)	0.0040 (13)	0.0142 (11)	0.0020 (12)
C11	0.0375 (16)	0.0301 (17)	0.0356 (15)	0.0031 (14)	0.0127 (13)	−0.0001 (13)
C9	0.0408 (16)	0.0295 (16)	0.0284 (14)	0.0016 (16)	0.0131 (12)	−0.0015 (14)
C10	0.0416 (16)	0.0334 (17)	0.0352 (14)	−0.0037 (15)	0.0116 (12)	0.0008 (15)
C10'	0.0427 (16)	0.0307 (16)	0.0313 (14)	0.0026 (15)	0.0106 (12)	−0.0056 (14)
C1	0.0453 (18)	0.046 (2)	0.0475 (18)	0.0005 (19)	0.0093 (14)	0.0020 (17)
C2	0.0461 (19)	0.053 (2)	0.0475 (19)	0.0078 (18)	0.0024 (15)	−0.0014 (17)
C3	0.060 (2)	0.044 (2)	0.0371 (17)	0.0147 (18)	0.0089 (15)	0.0060 (15)
C4	0.0555 (19)	0.041 (2)	0.0390 (17)	0.0035 (17)	0.0168 (14)	0.0040 (15)
C4'	0.0464 (17)	0.0265 (15)	0.0294 (14)	0.0033 (15)	0.0149 (13)	−0.0035 (13)
C5'	0.0432 (16)	0.0297 (15)	0.0306 (14)	0.0021 (15)	0.0157 (12)	−0.0040 (14)
C5	0.0552 (19)	0.036 (2)	0.0441 (18)	−0.0002 (17)	0.0247 (15)	0.0039 (15)
C6	0.0458 (19)	0.047 (2)	0.065 (2)	−0.0071 (18)	0.0282 (16)	0.0019 (18)
C7	0.0401 (18)	0.051 (2)	0.059 (2)	−0.0031 (18)	0.0148 (15)	0.0046 (19)
C8	0.0440 (18)	0.0402 (18)	0.0413 (17)	0.0011 (17)	0.0096 (14)	0.0018 (16)
C8'	0.0386 (15)	0.0285 (15)	0.0305 (14)	0.0027 (15)	0.0139 (12)	−0.0031 (14)

Geometric parameters (Å, º) top

O1—N1	1.405 (3)	C3—C4	1.363 (4)
O1—H	0.88 (3)	C3—H3	0.9300
N1—C11	1.268 (3)	C4—C4'	1.409 (4)
C11—C9	1.466 (4)	C4—H4	0.9300
C11—H11	0.9300	C4'—C5'	1.454 (4)
C9—C10	1.357 (3)	C5'—C5	1.408 (4)
C9—C8'	1.448 (4)	C5'—C8'	1.416 (4)
C10—C10'	1.422 (4)	C5—C6	1.364 (4)
C10—H10	0.9300	C5—H5	0.9300
C10'—C1	1.405 (4)	C6—C7	1.385 (4)
C10'—C4'	1.408 (4)	C6—H6	0.9300
C1—C2	1.365 (4)	C7—C8	1.365 (4)
C1—H1	0.9300	C7—H7	0.9300
C2—C3	1.384 (5)	C8—C8'	1.412 (4)
C2—H2	0.9300	C8—H8	0.9300

N1—O1—H	102 (2)	C3—C4—H4	119.5
C11—N1—O1	110.9 (2)	C4'—C4—H4	119.5
N1—C11—C9	121.2 (3)	C10'—C4'—C4	117.9 (2)
N1—C11—H11	119.4	C10'—C4'—C5'	119.2 (2)
C9—C11—H11	119.4	C4—C4'—C5'	122.9 (3)
C10—C9—C8'	119.6 (2)	C5—C5'—C8'	118.0 (2)
C10—C9—C11	120.0 (3)	C5—C5'—C4'	122.2 (3)
C8'—C9—C11	120.4 (2)	C8'—C5'—C4'	119.8 (2)
C9—C10—C10'	122.9 (3)	C6—C5—C5'	122.0 (3)
C9—C10—H10	118.6	C6—C5—H5	119.0
C10'—C10—H10	118.6	C5'—C5—H5	119.0
C1—C10'—C4'	119.8 (3)	C5—C6—C7	119.9 (3)
C1—C10'—C10	120.9 (3)	C5—C6—H6	120.1
C4'—C10'—C10	119.2 (2)	C7—C6—H6	120.1
C2—C1—C10'	120.6 (3)	C8—C7—C6	120.3 (3)
C2—C1—H1	119.7	C8—C7—H7	119.8
C10'—C1—H1	119.7	C6—C7—H7	119.8
C1—C2—C3	119.9 (3)	C7—C8—C8'	121.2 (3)
C1—C2—H2	120.1	C7—C8—H8	119.4
C3—C2—H2	120.1	C8'—C8—H8	119.4
C4—C3—C2	120.9 (3)	C8—C8'—C5'	118.6 (3)
C4—C3—H3	119.5	C8—C8'—C9	122.0 (3)
C2—C3—H3	119.5	C5'—C8'—C9	119.3 (2)
C3—C4—C4'	120.9 (3)

O1—N1—C11—C9	−175.3 (2)	C4—C4'—C5'—C5	−1.9 (4)
N1—C11—C9—C10	27.6 (4)	C10'—C4'—C5'—C8'	−0.5 (4)
N1—C11—C9—C8'	−156.1 (2)	C4—C4'—C5'—C8'	179.7 (3)
C8'—C9—C10—C10'	−0.2 (4)	C8'—C5'—C5—C6	0.2 (4)
C11—C9—C10—C10'	176.1 (3)	C4'—C5'—C5—C6	−178.2 (3)
C9—C10—C10'—C1	−179.3 (3)	C5'—C5—C6—C7	−0.1 (5)
C9—C10—C10'—C4'	−1.9 (4)	C5—C6—C7—C8	−0.1 (5)
C4'—C10'—C1—C2	0.4 (5)	C6—C7—C8—C8'	0.3 (5)
C10—C10'—C1—C2	177.9 (3)	C7—C8—C8'—C5'	−0.2 (4)
C10'—C1—C2—C3	0.0 (5)	C7—C8—C8'—C9	179.7 (3)
C1—C2—C3—C4	−0.2 (5)	C5—C5'—C8'—C8	−0.1 (4)
C2—C3—C4—C4'	0.0 (5)	C4'—C5'—C8'—C8	178.4 (3)
C1—C10'—C4'—C4	−0.5 (4)	C5—C5'—C8'—C9	−179.9 (2)
C10—C10'—C4'—C4	−178.1 (3)	C4'—C5'—C8'—C9	−1.5 (4)
C1—C10'—C4'—C5'	179.7 (3)	C10—C9—C8'—C8	−178.0 (3)
C10—C10'—C4'—C5'	2.2 (4)	C11—C9—C8'—C8	5.7 (4)
C3—C4—C4'—C10'	0.3 (4)	C10—C9—C8'—C5'	1.9 (4)
C3—C4—C4'—C5'	−179.9 (3)	C11—C9—C8'—C5'	−174.4 (2)
C10'—C4'—C5'—C5	177.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H···N1ⁱ	0.88 (3)	1.99 (3)	2.852 (3)	169 (3)

Symmetry code: (i) −x+1, y+1/2, −z+1.

Selected torsion angles (°) for the aldoxime groups in (I) and (II) top

	Compound (I)	Compound (II)
C1/C9—C11—N1—O1	-175.5 (4)	-175.3 (2)
C2/C10—C1/C9—C11—N1	23.6 (6)	27.6 (4)
C8'—C1—C11—N1	-160.4 (4)	–
C8'—C9—C11—N1	–	-156.1 (2)

Funding information

This project was funded by the Deanship of Scientific Research (DSR) at King Abdulaziz University, Jeddah, under grant No. (G-100–662-37). The authors, therefore, acknowledge with thanks the DSR for technical and financial support.

References

Asaad, N., Davies, J. E., Hodgson, D. R. W., Kirby, A. J., van Vliet, L. & Ottavi, L. (2005). J. Phys. Org. Chem. 18, 101–109. Web of Science CSD CrossRef CAS Google Scholar
Bruker (2016). APEX3, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruton, E. A., Brammer, L., Pigge, F. C., Aakeröy, C. B. & Leinen, D. S. (2003). New J. Chem. 27, 1084–1094. Web of Science CSD CrossRef CAS Google Scholar
Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. Web of Science CSD CrossRef IUCr Journals Google Scholar
Guo, Z., Li, L., Liu, G. & Dong, J. (2008). Acta Cryst. E64, o568. Web of Science CSD CrossRef IUCr Journals Google Scholar
Kassa, J. (2002). J. Toxicol. Clin. Toxicol. 40, 803–816. Web of Science CrossRef CAS Google Scholar
Kopylovich, M. N., Haukka, M., Kirillov, A. M., Kukushkin, V. Yu. & Pombeiro, A. J. L. (2007). Chem. Eur. J. 13, 786–791. Web of Science CSD CrossRef CAS Google Scholar
Kopylovich, M. N., Kukushkin, V. Yu., Guedes da Silva, M. F. C., Haukka, M., Fraústo da Silva, J. J. R. & Pombeiro, A. J. L. (2001). J. Chem. Soc. Perkin Trans. 1, pp. 1569–1573. Web of Science CSD CrossRef Google Scholar
Kopylovich, M. N., Kukushkin, V. Yu., Haukka, M., Fraústo da Silva, J. J. R. & Pombeiro, A. J. L. (2002). Inorg. Chem. 41, 4798–4804. Web of Science CSD CrossRef PubMed CAS Google Scholar
Kopylovich, M. N., Kukushkin, V. Yu., Haukka, M., Luzyanin, K. V. & Pombeiro, A. J. L. (2004). J. Am. Chem. Soc. 126, 15040–15041. Web of Science CSD CrossRef PubMed CAS Google Scholar
Kopylovich, M. N., Lasri, J., Guedes da Silva, M. F. C. & Pombeiro, A. J. L. (2009). Dalton Trans. pp. 3074–3084. Web of Science CSD CrossRef Google Scholar
Kukushkin, V. Yu. & Pombeiro, A. J. L. (1999). Coord. Chem. Rev. 181, 147–175. Web of Science CrossRef CAS Google Scholar
Lasri, J., Charmier, M. A. J., da Silva, M. F. C. G. & Pombeiro, A. J. L. (2007). Dalton Trans. pp. 3259–3266. Web of Science CSD CrossRef Google Scholar
Lasri, J., Guedes da Silva, M. F. C., Charmier, M. A. J. & Pombeiro, A. J. L. (2008). Eur. J. Inorg. Chem. pp. 3668–3677. Web of Science CSD CrossRef Google Scholar
Ritz, J., Fuchs, H., Kieczka, H. & Moran, W. C. (2012). Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Tarai, A. & Baruah, J. B. (2016). Cryst. Growth Des. 16, 126–135. Web of Science CSD CrossRef CAS Google Scholar

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Volume 74| Part 3| March 2018| Pages 332-336

https://doi.org/10.1107/S2056989018002116

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research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structures of (E)-1-naphthaldehyde oxime and (E)-phenanthrene-9-carbaldehyde oxime

1. Chemical context

2. Structural commentary

3. Supra­molecular features

4. Database survey

5. Synthesis and crystallization

6. Refinement

Supporting information

Funding information

References

research communications

3. Supramolecular features