Naphthalene-1-carbaldehyde oxime

Green, A.R.; Owczarzak, K.K.; Thomas, M.; Olrogg, G.M.; Whitver, E.; Crescente, J.V.; Peters, J.; Doud, C.M.; Storm, M.M.; Fink, K.D.; Bilotti, C.; Cardenas, A.J.

doi:10.1107/S2414314617017205

organic compounds

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Naphthalene-1-carbaldehyde oxime

^a325 Science Center, State University of New York at Fredonia, Fredonia, NY 14063, USA
^*Correspondence e-mail: allan.cardenas@fredonia.edu

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 31 October 2017; accepted 29 November 2017; online 5 December 2017)

The title compound, C₁₁H₉NO, crystallizes with two molecules, A and B, with similar conformations (r.m.s. overlay fit = 0.030 Å) in the asymmetric unit: the C—C=N⋯O torsion angles are −177.8 (3) and −179.1 (3)°. In the crystal, molecules are linked by alternating O—H⋯N (A → B) and O—H⋯O (B → A) hydrogen bonds to generate [100] chains. A weak C—H⋯O interaction is also observed.

Keywords: crystal structure; hydrogen bonds; nitroxyl donor; oxime; non-conventional hydrogen bond.

CCDC reference: 1588319

Structure description

Compounds containing the oxime functional group have been the subject of interest for many years due to many their functions as synthetic congeners or precursors, as substrates for bioconjugation reaction (Kömel & Kool, 2017 ) and also as nitroxyl (HNO) donors (Sha et al., 2006 ). Oximes are generally reactive; however, conjugation leads to an increase in stability of this functional group (Kömel, 2017), which is observed in the title compound that was studied as part of an undergraduate project devoted to single-crystal X-ray diffraction.

The title compound crystallizes in the orthorhombic crystal system, space group P2₁2₁2₁. There are two molecules, A (containing N1) and B (containing N2) in the asymmetric unit (Fig. 1). The bond distances for the oxime functional group are 1.281 (4) and 1.399 (4) Å for C1=N1 and N1—O1, respectively (molecule A) and 1.278 (5) and 1.401 (4) Å for C12=N2 and N2—O2, respectively (molecule B). The angle for C=N—O is 111.0 (3) (molecule A) and 111.3 (3)° (molecule B). These values are comparable to those in the same molecule co-crystallized with tetrabutylammonium cations and fluoride anions (Rosen et al., 2013 ).

Figure 1
A view of the molecular structure, showing 50% probability displacement ellipsoids.

In the extended structure, O—H⋯N (A –> B) and O—H⋯O (B –> A) hydrogen bonds link the molecules into [100] chains (Table 1, Fig. 2). A weak C—H⋯O interaction is also observed.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N2	0.84 (2)	1.96 (2)	2.752 (4)	158 (3)
O2—H2⋯O1ⁱ	0.84 (1)	2.00 (2)	2.808 (4)	163 (2)
C1—H1A⋯O2ⁱⁱ	0.95 (1)	2.51 (1)	3.305 (5)	142 (1)
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ .

Figure 2
A view down [100] of the crystal packing. The hydrogen bonds are shown as dashed lines.

Synthesis and crystallization

The title oxime was synthesized using the reported procedure of Rosen et al. (2013). Colourless needles were recrystallized from dichloromethane solution.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The absolute structure/chirality was indeterminate in the present refinement.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₁H₉NO
M_r	171.20
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	150
a, b, c (Å)	6.0506 (8), 13.7423 (18), 20.886 (3)
V (Å³)	1736.7 (4)
Z	8
Radiation type	Mo Kα
μ (mm⁻¹)	0.09
Crystal size (mm)	0.50 × 0.10 × 0.10

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2016)
T_min, T_max	0.678, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	8745, 3390, 2106
R_int	0.077
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.069, 0.139, 1.04
No. of reflections	3390
No. of parameters	237
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.46
Computer programs: APEX2 and SAINT (Bruker, 2016 ), SHELXT (Sheldrick, 2015 ), olex2.refine (Bourhis et al., 2015 ) and OLEX2 (Dolomanov et al., 2009 ).

Structural data

CCDC reference: 1588319

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314617017205/hb4179sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617017205/hb4179Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617017205/hb4179Isup3.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015); program(s) used to refine structure: olex2.refine (Bourhis et al., 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Naphthalene-1-carbaldehyde oxime top

Crystal data top

C₁₁H₉NO	D_x = 1.309 Mg m⁻³
M_r = 171.20	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 1679 reflections
a = 6.0506 (8) Å	θ = 3.1–27.3°
b = 13.7423 (18) Å	µ = 0.09 mm⁻¹
c = 20.886 (3) Å	T = 150 K
V = 1736.7 (4) Å³	Needle, clear colourless
Z = 8	0.50 × 0.10 × 0.10 mm
F(000) = 720.3282

Data collection top

Bruker APEXII CCD diffractometer	R_int = 0.077
Absorption correction: multi-scan (SADABS; Bruker, 2016)	θ_max = 26.0°, θ_min = 3.3°
T_min = 0.678, T_max = 0.746	h = −7→7
8745 measured reflections	k = −18→16
3390 independent reflections	l = −26→27
2106 reflections with I > 2σ(I)

Refinement top

Refinement on F²	36 constraints
Least-squares matrix: full	Primary atom site location: dual
R[F² > 2σ(F²)] = 0.069	All H-atom parameters refined
wR(F²) = 0.139	w = 1/[σ²(F_o²) + (0.0462P)² + 0.5394P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.002
3390 reflections	Δρ_max = 0.40 e Å⁻³
237 parameters	Δρ_min = −0.46 e Å⁻³
0 restraints	Absolute structure: unk

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

	x	y	z	U_iso*/U_eq
O1	0.8084 (5)	0.74706 (19)	0.04014 (14)	0.0416 (8)
H1	0.823 (5)	0.8017 (9)	0.0227 (16)	0.0624 (11)*
N1	0.6345 (5)	0.7510 (2)	0.08423 (14)	0.0314 (8)
C1	0.5986 (7)	0.6671 (3)	0.10891 (17)	0.0315 (10)
H1a	0.6895 (7)	0.6136 (3)	0.09740 (17)	0.0378 (12)*
C2	0.4174 (6)	0.6533 (3)	0.15500 (17)	0.0256 (9)
C3	0.2503 (7)	0.7215 (3)	0.1597 (2)	0.0355 (10)
H3	0.2534 (7)	0.7774 (3)	0.1330 (2)	0.0426 (13)*
C4	0.0769 (7)	0.7093 (3)	0.2030 (2)	0.0421 (11)
H4	−0.0347 (7)	0.7577 (3)	0.2061 (2)	0.0505 (14)*
C5	0.0664 (7)	0.6287 (3)	0.2408 (2)	0.0415 (12)
H5	−0.0535 (7)	0.6211 (3)	0.2698 (2)	0.0498 (14)*
C6	0.2303 (7)	0.5570 (3)	0.23757 (16)	0.0313 (10)
C7	0.2237 (7)	0.4731 (3)	0.27754 (18)	0.0403 (11)
H7	0.1044 (7)	0.4645 (3)	0.30657 (18)	0.0484 (14)*
C8	0.3859 (8)	0.4055 (3)	0.27451 (19)	0.0452 (12)
H8	0.3778 (8)	0.3495 (3)	0.30107 (19)	0.0543 (15)*
C9	0.5660 (7)	0.4168 (3)	0.23276 (18)	0.0380 (11)
H9	0.6797 (7)	0.3691 (3)	0.23166 (18)	0.0456 (13)*
C10	0.5776 (7)	0.4967 (3)	0.19358 (18)	0.0301 (9)
H10	0.6994 (7)	0.5036 (3)	0.16521 (18)	0.0361 (11)*
C11	0.4108 (6)	0.5691 (3)	0.19476 (17)	0.0243 (9)
O2	0.5555 (5)	0.92557 (18)	−0.04725 (14)	0.0380 (7)
H2	0.507 (4)	0.8683 (8)	−0.0472 (17)	0.0570 (11)*
N2	0.7406 (5)	0.9316 (2)	−0.00713 (14)	0.0285 (8)
C12	0.7995 (6)	1.0199 (3)	0.00150 (17)	0.0297 (9)
H12	0.7167 (6)	1.0704 (3)	−0.01825 (17)	0.0356 (11)*
C13	0.9902 (6)	1.0455 (2)	0.04078 (16)	0.0244 (9)
C14	1.1498 (6)	0.9772 (3)	0.05384 (17)	0.0286 (9)
H14	1.1352 (6)	0.9136 (3)	0.03645 (17)	0.0343 (11)*
C15	1.3321 (7)	0.9985 (3)	0.09178 (17)	0.0335 (10)
H15	1.4389 (7)	0.9496 (3)	0.10032 (17)	0.0402 (12)*
C16	1.3585 (7)	1.0891 (3)	0.11676 (18)	0.0359 (10)
H16	1.4837 (7)	1.1031 (3)	0.14262 (18)	0.0431 (12)*
C17	1.2003 (6)	1.1630 (3)	0.10446 (16)	0.0270 (9)
C18	1.2236 (7)	1.2576 (3)	0.13064 (17)	0.0356 (11)
H18	1.3501 (7)	1.2724 (3)	0.15579 (17)	0.0428 (13)*
C19	1.0696 (8)	1.3274 (3)	0.12058 (19)	0.0383 (11)
H19	1.0872 (8)	1.3900 (3)	0.13919 (19)	0.0460 (13)*
C20	0.8845 (8)	1.3073 (3)	0.08279 (18)	0.0356 (11)
H20	0.7776 (8)	1.3568 (3)	0.07551 (18)	0.0428 (13)*
C21	0.8553 (7)	1.2169 (3)	0.05604 (18)	0.0322 (10)
H21	0.7290 (7)	1.2043 (3)	0.03031 (18)	0.0386 (12)*
C22	1.0139 (6)	1.1419 (3)	0.06679 (16)	0.0244 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0419 (17)	0.0351 (17)	0.0478 (17)	0.0067 (16)	0.0178 (16)	0.0087 (14)
N1	0.029 (2)	0.036 (2)	0.0295 (17)	0.0005 (18)	0.0009 (17)	0.0025 (16)
C1	0.035 (2)	0.026 (2)	0.034 (2)	0.006 (2)	0.003 (2)	0.0017 (18)
C2	0.023 (2)	0.025 (2)	0.029 (2)	−0.004 (2)	−0.0020 (19)	−0.0052 (17)
C3	0.029 (2)	0.032 (2)	0.046 (2)	0.001 (2)	−0.010 (2)	−0.005 (2)
C4	0.025 (2)	0.043 (3)	0.059 (3)	0.004 (2)	0.001 (3)	−0.019 (2)
C5	0.024 (2)	0.051 (3)	0.049 (3)	−0.011 (2)	0.012 (2)	−0.023 (2)
C6	0.027 (2)	0.044 (3)	0.023 (2)	−0.009 (2)	−0.0017 (19)	−0.0135 (19)
C7	0.034 (3)	0.055 (3)	0.032 (2)	−0.024 (3)	0.002 (2)	−0.002 (2)
C8	0.050 (3)	0.046 (3)	0.040 (3)	−0.020 (3)	−0.018 (2)	0.014 (2)
C9	0.035 (3)	0.036 (2)	0.042 (2)	−0.009 (2)	−0.009 (2)	0.006 (2)
C10	0.024 (2)	0.029 (2)	0.037 (2)	−0.006 (2)	−0.002 (2)	0.0026 (18)
C11	0.022 (2)	0.026 (2)	0.0246 (19)	−0.0066 (19)	−0.0037 (19)	−0.0070 (17)
O2	0.0285 (15)	0.0326 (15)	0.0530 (17)	−0.0075 (15)	−0.0088 (16)	−0.0036 (15)
N2	0.0243 (18)	0.0275 (18)	0.0336 (17)	0.0001 (16)	0.0037 (17)	−0.0038 (15)
C12	0.029 (2)	0.027 (2)	0.034 (2)	−0.0015 (19)	−0.002 (2)	−0.0004 (18)
C13	0.029 (2)	0.0231 (19)	0.0207 (18)	−0.0050 (18)	0.0014 (18)	0.0042 (16)
C14	0.029 (2)	0.028 (2)	0.029 (2)	0.006 (2)	0.002 (2)	0.0020 (18)
C15	0.029 (2)	0.039 (3)	0.033 (2)	0.005 (2)	0.000 (2)	0.002 (2)
C16	0.026 (2)	0.054 (3)	0.028 (2)	−0.001 (2)	−0.002 (2)	0.005 (2)
C17	0.022 (2)	0.037 (2)	0.0222 (19)	−0.0055 (19)	0.0010 (19)	0.0054 (18)
C18	0.037 (3)	0.043 (3)	0.027 (2)	−0.010 (2)	−0.001 (2)	0.000 (2)
C19	0.053 (3)	0.024 (2)	0.038 (2)	−0.005 (2)	0.005 (2)	−0.0056 (19)
C20	0.041 (3)	0.026 (2)	0.039 (2)	0.000 (2)	0.004 (2)	−0.004 (2)
C21	0.033 (3)	0.034 (2)	0.029 (2)	−0.005 (2)	−0.002 (2)	0.0068 (19)
C22	0.025 (2)	0.025 (2)	0.023 (2)	−0.0016 (18)	0.0026 (17)	0.0070 (16)

Geometric parameters (Å, º) top

O1—H1	0.839 (18)	O2—H2	0.840 (13)
O1—N1	1.399 (4)	O2—N2	1.401 (4)
N1—C1	1.281 (4)	N2—C12	1.277 (4)
C1—H1a	0.9500 (6)	C12—H12	0.951 (6)
C1—C2	1.471 (5)	C12—C13	1.459 (5)
C2—C3	1.381 (5)	C13—C14	1.374 (5)
C2—C11	1.425 (5)	C13—C22	1.439 (5)
C3—H3	0.9500 (6)	C14—H14	0.949 (6)
C3—C4	1.395 (6)	C14—C15	1.389 (5)
C4—H4	0.951 (6)	C15—H15	0.950 (6)
C4—C5	1.362 (6)	C15—C16	1.359 (5)
C5—H5	0.950 (6)	C16—H16	0.950 (6)
C5—C6	1.401 (6)	C16—C17	1.418 (6)
C6—C7	1.424 (6)	C17—C18	1.418 (5)
C6—C11	1.421 (5)	C17—C22	1.405 (5)
C7—H7	0.950 (6)	C18—H18	0.950 (6)
C7—C8	1.352 (6)	C18—C19	1.353 (6)
C8—H8	0.951 (6)	C19—H19	0.951 (6)
C8—C9	1.404 (6)	C19—C20	1.398 (6)
C9—H9	0.950 (6)	C20—H20	0.950 (6)
C9—C10	1.371 (5)	C20—C21	1.374 (5)
C10—H10	0.950 (6)	C21—H21	0.950 (6)
C10—C11	1.418 (5)	C21—C22	1.426 (5)

N1—O1—H1	109 (2)	N2—O2—H2	110 (2)
C1—N1—O1	111.0 (3)	C12—N2—O2	111.3 (3)
H1a—C1—N1	119.8 (2)	H12—C12—N2	119.0 (2)
C2—C1—N1	120.4 (4)	C13—C12—N2	121.9 (4)
C2—C1—H1a	119.8 (2)	C13—C12—H12	119.0 (2)
C3—C2—C1	120.3 (3)	C14—C13—C12	120.2 (3)
C11—C2—C1	120.4 (3)	C22—C13—C12	120.9 (3)
C11—C2—C3	119.3 (4)	C22—C13—C14	118.9 (3)
H3—C3—C2	119.5 (2)	H14—C14—C13	119.1 (2)
C4—C3—C2	121.0 (4)	C15—C14—C13	121.8 (4)
C4—C3—H3	119.5 (3)	C15—C14—H14	119.1 (2)
H4—C4—C3	119.7 (3)	H15—C15—C14	119.8 (2)
C5—C4—C3	120.6 (4)	C16—C15—C14	120.4 (4)
C5—C4—H4	119.7 (3)	C16—C15—H15	119.8 (3)
H5—C5—C4	119.6 (3)	H16—C16—C15	119.8 (3)
C6—C5—C4	120.7 (4)	C17—C16—C15	120.4 (4)
C6—C5—H5	119.6 (2)	C17—C16—H16	119.8 (2)
C7—C6—C5	121.4 (4)	C18—C17—C16	121.3 (4)
C11—C6—C5	119.5 (4)	C22—C17—C16	119.7 (4)
C11—C6—C7	119.0 (4)	C22—C17—C18	119.0 (4)
H7—C7—C6	119.7 (3)	H18—C18—C17	119.3 (2)
C8—C7—C6	120.5 (4)	C19—C18—C17	121.4 (4)
C8—C7—H7	119.7 (3)	C19—C18—H18	119.3 (2)
H8—C8—C7	119.5 (3)	H19—C19—C18	120.0 (2)
C9—C8—C7	121.1 (4)	C20—C19—C18	120.0 (4)
C9—C8—H8	119.5 (3)	C20—C19—H19	120.0 (2)
H9—C9—C8	120.1 (3)	H20—C20—C19	119.6 (2)
C10—C9—C8	119.9 (4)	C21—C20—C19	120.7 (4)
C10—C9—H9	120.1 (3)	C21—C20—H20	119.6 (3)
H10—C10—C9	119.5 (3)	H21—C21—C20	119.9 (3)
C11—C10—C9	121.0 (4)	C22—C21—C20	120.2 (4)
C11—C10—H10	119.5 (2)	C22—C21—H21	119.9 (2)
C6—C11—C2	118.9 (3)	C17—C22—C13	118.8 (3)
C10—C11—C2	122.7 (3)	C21—C22—C13	122.6 (3)
C10—C11—C6	118.4 (3)	C21—C22—C17	118.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2	0.84 (2)	1.96 (2)	2.752 (4)	158 (3)
O2—H2···O1ⁱ	0.84 (1)	2.00 (2)	2.808 (4)	163 (2)
C1—H1A···O2ⁱⁱ	0.95 (1)	2.51 (1)	3.305 (5)	142 (1)

Symmetry codes: (i) x−1/2, −y+3/2, −z; (ii) x+1/2, −y+3/2, −z.

Funding information

The authors thank the Department of Chemistry and Biochemistry of the State University of New York at Fredonia for funding and use of the diffractometer.

References

Bourhis, L. J., Dolomanov, O. V., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2015). Acta Cryst. A71, 59–75. Web of Science CrossRef IUCr Journals Google Scholar
Bruker (2016). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Kölmel, D. K. & Kool, E. T. (2017). Chem. Rev. 117, 10358–10376. Web of Science PubMed Google Scholar
Rosen, C. B., Hansen, J. D. & Gothelf, K. V. (2013). Org. Biomol. Chem. 11, 7916–7922. Web of Science CSD CrossRef CAS PubMed Google Scholar
Sha, X., Isbell, S., Patel, R. P., Day, C. S. & King, B. (2006). J. Am. Chem. Soc. 128, 9687–9692. Web of Science CSD CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Naphthalene-1-carbaldehyde oxime

Structure description

Synthesis and crystallization

Refinement

Structural data

Funding information

References

organic compounds