Salicylaldoxime-III at 150 K

Wood, P.A.; Forgan, R.S.; Parsons, S.; Pidcock, E.; Tasker, P.A.

doi:10.1107/S1600536806032375

organic compounds

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Volume 62| Part 9| September 2006| Pages o3944-o3946

https://doi.org/10.1107/S1600536806032375

Salicylaldoxime-III at 150 K

Peter A. Wood,^a Ross S. Forgan,^a Simon Parsons,^a ^* Elna Pidcock ^b and Peter A. Tasker ^a

^aSchool of Chemistry, University of Edinburgh, King's Buildings, West Mains Road, Edinburgh EH9 3JJ, Scotland, and ^bCambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, England
^*Correspondence e-mail: s.parsons@ed.ac.uk

(Received 13 August 2006; accepted 15 August 2006; online 18 August 2006)

Salicylaldoxime derivatives crystallize in either hydrogen-bonded ring or chain motifs. A polymorph of the parent compound, salicylaldoxime, characterized by ring formation, has been known for some time. We now report a new polymorph of salicylaldoxime (2-hydroxybenzaldehyde oxime, C₇H₇NO₂), which exhibits chain formation and which has two molecules per asymmetric unit. π–π stacking interactions occur between the chains. We refer to this polymorph as salicylaldoxime-III.

Comment

Salicylaldoximes bearing branched alkyl chains are used as extractants to effect the separation and concentration operations in the hydrometallurgical recovery of copper, accounting for around 30% of annual production (Kordosky, 2002 ). The N₂O₂²⁻ donor set in bis-salicylaldoxime complexes is stabilized by interligand hydrogen bonds, forming a pseudomacrocyclic arrangement (e.g. Fig. 1a). The high selectivity of salicylaldoximes for copper over other metal ions is the result of the compatibility of the size of the cavity at the centre of the pseudo-macrocycle and the ionic radius of Cu²⁺ (Smith et al., 2002 ).

The crystal structure of the parent compound salicylaldoxime, (1), was determined using X-ray diffraction by Pfluger & Harlow (1973 ) [Cambridge Structural Database (CSD, Version 5.27; Allen, 2002 ) refcode SALOXM]. We refer to the phase investigated by these workers as salicylaldoxime-I. We have recently shown that salicylaldoxime-I undergoes a phase transition at 5.3 GPa to a second phase, salicylaldoxime-II (Wood et al., 2006 ).

Salicylaldoxime-I crystallizes in space group P2₁/n. Pairs of molecules, related by inversion centres, form intermolecular O—H⋯O hydrogen bonds to produce a dimer (Fig. 1b), for which the graph-set descriptor is R₄⁴(10) (Bernstein et al., 1995 ). This dimeric form closely resembles the pseudo-macrocyclic arrangement observed in metal complexes, and is only observed in the free ligands in the solid state in salicylaldoxime derivatives which carry small substituents [e.g. CSD refcodes ABULIT (Xu et al., 2004 ) and CLSALX (Simonsen et al., 1961 )]. Bulky alkyl substituents lead to hydrogen-bonded chain motifs in preference to rings [e.g. CSD refcodes HEPKET10 (Koziol & Kosturkiewicz, 1984 ) and HELBOP (Maurin, 1994 )].

We now report the crystal structure of a third polymorph of salicylaldoxime, salicylaldoxime-III, obtained under ambient conditions by recrystallization from a solution of hexane and chloroform. Weissenberg photographs, taken using a crystal of salicylaldoxime obtained from alcohol, were indexed by Merritt & Schroeder (1956 ) on the basis of an orthorhombic cell with dimensions a = 12.69, b = 13.51 and c = 7.98 Å, although no coordinates were determined. These cell dimensions closely resemble those determined here for salicylaldoxime-III. In the same paper, the authors report a powder pattern, which Pfluger & Harlow (1973) claim actually corresponds to the monoclinic form, salicylaldoxime-I. However, a powder pattern simulated (using PLATON; Spek, 2006 ) on the basis of the structural parameters reported here for phase III more closely resembles the data reported by Merritt & Schroeder (1956) than the pattern calculated for phase I (sourcing coordinates from CSD refcode SALOXM). For example, the first six simulated d spacings for form III are 6.89, 6.36, 5.89, 5.74, 5.04 and 4.61 Å; the corresponding data for phase I are 9.59, 6.54, 6.26, 4.82, 4.71 and 4.50 Å, while the data reported by Merritt & Schroeder are 6.76, 6.32, 5.99, 5.68, 5.10 and 4.58 Å. We therefore disagree with Pfluger & Harlow's conclusion regarding the pattern reported by Merritt & Schroeder.

Salicylaldoxime-III is characterized by the formation of hydrogen-bonded chains rather than hydrogen-bonded rings. There are two molecules in the asymmetric unit of salicylaldoxime-III (Fig. 2), which alternate along a hydrogen-bonded chain formed by intermolecular oximic O—H⋯O hydrogen bonds (Fig. 3). The chains run along the crystallographic c axis, being generated by a ..2₁ operation. Intramolecular phenolic O—H⋯N hydrogen bonds are also formed (Fig. 3).

The chains interact with each other via π–π stacking contacts formed between two symmetry-independent molecules. Within these stacking interactions, the atoms forming the phenyl ring of molecule 2 (based on O12 etc.) lie between 3.394 (2) and 3.519 (2) Å from the mean plane of molecule 1 (based on O11). The dihedral angle between the two phenyl planes is 2.69 (5)°.

Figure 1
Pseudomacrocycle formation by salicylaldoxime. (a) Salicylaldoxime complexation by copper(II). (b) Hydogen-bonded dimers formed in the crystal structure of salicylaldoxime-I. Dashed lines indicate hydrogen bonds.

Figure 2
The two molecules comprising the asymmetric unit of salicylaldoxime-III. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as circles of arbitrary radii. Dashed lines indicate hydrogen bonds.

Figure 3
Hydrogen-bonded chains in salicylaldoxime-III. Dashed lines indicate hydrogen bonds.

Experimental

Salicylaldoxime was obtained from Acros. The solid was dissolved in chloroform and enough hexane was added to induce precipitation of a small quality of solid. Chloroform was added to redissolve the precipitated solid, and the solution was filtered into a small beaker through glass wool. Crystals of salicylaldoxime grew on allowing the solution to evaporate over the course of 5 d at room temperature.

Crystal data

C₇H₇NO₂
M_r = 137.14
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.6691 (2) Å
b = 12.7162 (3) Å
c = 13.3652 (3) Å
V = 1303.40 (5) Å³
Z = 8
D_x = 1.398 Mg m⁻³
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 150 K
Block, colourless
0.42 × 0.25 × 0.18 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
ω scans
Absorption correction: multi-scan (SADABS; Sheldrick, 2006 ) T_min = 0.740, T_max = 0.980
15665 measured reflections
1886 independent reflections
1618 reflections with I > 2σ(I)
R_int = 0.061
θ_max = 28.9°

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.079
S = 0.94
1886 reflections
194 parameters
H atoms treated by a mixture of independent and constrained refinement
w = 1/[σ²(F²) + (0.04P)²], where P = [max(F_o²,0) + 2F_c²]/3
(Δ/σ)_max < 0.001
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.28 e Å⁻³
Extinction correction: Larson (1970 ), equation 22
Extinction coefficient: 2.2 (2) × 10²

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O11—H11⋯O52ⁱ	0.81 (2)	2.01 (2)	2.8137 (17)	176 (2)
O12—H12⋯O51ⁱⁱ	0.87 (2)	1.99 (2)	2.7945 (18)	155 (2)
O51—H51⋯N21	0.86 (2)	1.85 (2)	2.6384 (18)	152 (2)
O52—H52⋯N22	0.85 (2)	1.84 (2)	2.6285 (18)	153.4 (19)
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

H atoms on O atoms (H11, H51, H12 and H52) were found in a difference Fourier map and their positions refined, subject to O—H distance restraints of 0.84 (5) Å and with U_iso(H) = 1.2U_eq(O). The remaining H atoms were positioned geometrically and constrained to ride on their host atoms, with C—H = 0.93–0.96 Å and with U_iso(H) = 1.2U_eq(C).

Data on this light-atom structure were collected with Mo Kα radiation, and dispersion effects are negligible. The absolute configuration of the crystal used for data collection has not been determined in this study. Friedel pairs were merged.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT; data reduction: SAINT (Bruker, 2003 ); program(s) used to solve structure: SIR92 (Altomare et al., 1994 ); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ); molecular graphics: DIAMOND (Brandenburg, 2006 ) and XP (Sheldrick, 1997 ); software used to prepare material for publication: CRYSTALS and PLATON (Spek, 2006).

Supporting information

Crystal structure: contains datablocks global, 1. DOI: https://doi.org/10.1107/S1600536806032375/bt2170sup1.cif

Structure factors: contains datablock 1. DOI: https://doi.org/10.1107/S1600536806032375/bt21701sup2.hkl

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT; data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: DIAMOND (Brandenburg, 2006) and XP (Sheldrick, 1997); software used to prepare material for publication: CRYSTALS and PLATON (Spek, 2006).

2-hydroxybenzaldehyde oxime top

Crystal data top

C₇H₇NO₂	D_x = 1.398 Mg m⁻³
M_r = 137.14	Melting point = 332–334 K
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 7295 reflections
a = 7.6691 (2) Å	θ = 2–28°
b = 12.7162 (3) Å	µ = 0.10 mm⁻¹
c = 13.3652 (3) Å	T = 150 K
V = 1303.40 (5) Å³	Block, colourless
Z = 8	0.42 × 0.25 × 0.18 mm
F(000) = 576

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	1618 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.061
ω scans	θ_max = 28.9°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2006)	h = −10→9
T_min = 0.740, T_max = 0.980	k = −17→16
15665 measured reflections	l = −17→17
1886 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: geom/difmap
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.033	w = 1/[σ²(F²) + (0.04P)²], where P = [max(F_o²,0) + 2F_c²]/3
wR(F²) = 0.079	(Δ/σ)_max = 0.000152
S = 0.94	Δρ_max = 0.22 e Å⁻³
1886 reflections	Δρ_min = −0.28 e Å⁻³
194 parameters	Extinction correction: Larson (1970), Equation 22
4 restraints	Extinction coefficient: 220 (20)
Primary atom site location: structure-invariant direct methods

Special details top

Experimental. Used Oxford Cryosystems low-temperature device.

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

	x	y	z	U_iso*/U_eq
O11	0.2811 (2)	0.27564 (10)	0.02463 (9)	0.0368
N21	0.2508 (2)	0.22621 (10)	0.11662 (10)	0.0274
C31	0.1828 (2)	0.13549 (13)	0.10589 (12)	0.0264
C41	0.1437 (2)	0.07010 (13)	0.19232 (12)	0.0242
C51	0.1779 (2)	0.10191 (12)	0.29136 (12)	0.0238
O51	0.24867 (17)	0.19816 (9)	0.31221 (9)	0.0286
C61	0.1421 (2)	0.03505 (14)	0.37079 (12)	0.0291
C71	0.0716 (2)	−0.06313 (14)	0.35366 (14)	0.0322
C81	0.0356 (2)	−0.09565 (14)	0.25657 (15)	0.0313
C91	0.0725 (2)	−0.02997 (13)	0.17736 (13)	0.0285
O12	0.7865 (2)	0.25663 (11)	0.48433 (10)	0.0407
N22	0.7161 (2)	0.16559 (10)	0.44076 (11)	0.0286
C32	0.7209 (2)	0.17066 (12)	0.34528 (13)	0.0275
C42	0.6555 (2)	0.08496 (13)	0.28352 (12)	0.0246
C52	0.5891 (2)	−0.00828 (12)	0.32393 (11)	0.0243
O52	0.58579 (17)	−0.02492 (9)	0.42557 (8)	0.0308
C62	0.5244 (2)	−0.08673 (13)	0.26243 (13)	0.0286
C72	0.5285 (2)	−0.07423 (14)	0.15954 (13)	0.0303
C82	0.5959 (2)	0.01694 (14)	0.11784 (12)	0.0298
C92	0.6577 (2)	0.09598 (13)	0.17902 (12)	0.0275
H11	0.315 (3)	0.3334 (17)	0.0410 (18)	0.0537*
H31	0.1580	0.1096	0.0427	0.0315*
H51	0.270 (3)	0.2251 (17)	0.2545 (15)	0.0427*
H61	0.1667	0.0573	0.4365	0.0331*
H71	0.0482	−0.1061	0.4091	0.0397*
H81	−0.0141	−0.1634	0.2458	0.0370*
H91	0.0544	−0.0523	0.1101	0.0330*
H12	0.768 (3)	0.2501 (18)	0.5479 (17)	0.0593*
H32	0.7654	0.2305	0.3130	0.0324*
H52	0.624 (3)	0.0323 (16)	0.4501 (15)	0.0450*
H62	0.4761	−0.1487	0.2923	0.0336*
H72	0.4791	−0.1260	0.1180	0.0364*
H82	0.5949	0.0260	0.0472	0.0363*
H92	0.7026	0.1581	0.1508	0.0322*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O11	0.0607 (9)	0.0291 (7)	0.0207 (6)	−0.0041 (7)	0.0001 (6)	0.0029 (5)
N21	0.0348 (8)	0.0267 (7)	0.0206 (6)	0.0048 (6)	−0.0006 (6)	0.0018 (5)
C31	0.0299 (8)	0.0279 (8)	0.0213 (7)	0.0046 (7)	−0.0029 (7)	−0.0036 (7)
C41	0.0215 (7)	0.0248 (8)	0.0264 (8)	0.0037 (7)	−0.0003 (7)	−0.0010 (6)
C51	0.0237 (8)	0.0222 (8)	0.0253 (8)	0.0036 (6)	0.0011 (7)	−0.0017 (6)
O51	0.0410 (7)	0.0236 (5)	0.0213 (5)	−0.0023 (6)	0.0000 (6)	−0.0016 (5)
C61	0.0332 (8)	0.0293 (8)	0.0246 (8)	0.0022 (8)	0.0040 (7)	−0.0017 (7)
C71	0.0338 (9)	0.0281 (9)	0.0348 (9)	0.0023 (8)	0.0098 (8)	0.0033 (7)
C81	0.0283 (8)	0.0250 (8)	0.0408 (10)	−0.0019 (7)	0.0048 (8)	−0.0048 (7)
C91	0.0263 (8)	0.0281 (8)	0.0310 (9)	0.0010 (8)	−0.0024 (7)	−0.0070 (7)
O12	0.0677 (10)	0.0285 (6)	0.0259 (6)	−0.0054 (7)	−0.0019 (7)	−0.0051 (6)
N22	0.0384 (8)	0.0223 (6)	0.0252 (7)	0.0037 (7)	−0.0003 (6)	−0.0021 (6)
C32	0.0339 (9)	0.0233 (8)	0.0254 (8)	0.0024 (7)	0.0024 (7)	0.0018 (6)
C42	0.0243 (7)	0.0263 (8)	0.0231 (7)	0.0057 (7)	0.0017 (7)	−0.0012 (6)
C52	0.0250 (8)	0.0276 (8)	0.0204 (7)	0.0056 (7)	0.0023 (7)	0.0005 (7)
O52	0.0442 (7)	0.0275 (6)	0.0208 (6)	−0.0037 (6)	0.0028 (6)	0.0023 (5)
C62	0.0287 (8)	0.0271 (9)	0.0300 (9)	0.0009 (7)	−0.0016 (7)	0.0003 (7)
C72	0.0290 (8)	0.0327 (9)	0.0292 (9)	0.0051 (8)	−0.0049 (8)	−0.0069 (7)
C82	0.0314 (8)	0.0392 (9)	0.0187 (7)	0.0085 (8)	−0.0003 (7)	−0.0018 (7)
C92	0.0305 (8)	0.0290 (8)	0.0229 (8)	0.0043 (8)	0.0021 (7)	0.0030 (7)

Geometric parameters (Å, º) top

O11—N21	1.4003 (17)	O12—N22	1.4039 (19)
O11—H11	0.81 (2)	O12—H12	0.86 (2)
N21—C31	1.274 (2)	N22—C32	1.278 (2)
C31—C41	1.454 (2)	C32—C42	1.456 (2)
C31—H31	0.927	C32—H32	0.939
C41—C51	1.409 (2)	C42—C52	1.399 (2)
C41—C91	1.399 (2)	C42—C92	1.404 (2)
C51—O51	1.3677 (19)	C52—O52	1.3751 (19)
C51—C61	1.388 (2)	C52—C62	1.385 (2)
O51—H51	0.86 (2)	O52—H52	0.85 (2)
C61—C71	1.379 (3)	C62—C72	1.385 (2)
C61—H61	0.942	C62—H62	0.958
C71—C81	1.390 (3)	C72—C82	1.386 (2)
C71—H71	0.938	C72—H72	0.941
C81—C91	1.378 (2)	C82—C92	1.380 (2)
C81—H81	0.953	C82—H82	0.951
C91—H91	0.953	C92—H92	0.940

N21—O11—H11	102.9 (17)	N22—O12—H12	105.4 (16)
O11—N21—C31	112.06 (13)	O12—N22—C32	111.20 (14)
N21—C31—C41	120.83 (15)	N22—C32—C42	121.23 (16)
N21—C31—H31	120.6	N22—C32—H32	120.7
C41—C31—H31	118.6	C42—C32—H32	118.1
C31—C41—C51	122.95 (14)	C32—C42—C52	122.73 (14)
C31—C41—C91	119.13 (15)	C32—C42—C92	119.02 (15)
C51—C41—C91	117.91 (15)	C52—C42—C92	118.24 (15)
C41—C51—O51	121.49 (14)	C42—C52—O52	121.24 (14)
C41—C51—C61	120.41 (15)	C42—C52—C62	120.80 (14)
O51—C51—C61	118.10 (14)	O52—C52—C62	117.96 (15)
C51—O51—H51	104.4 (14)	C52—O52—H52	104.1 (14)
C51—C61—C71	120.34 (16)	C52—C62—C72	119.92 (16)
C51—C61—H61	119.3	C52—C62—H62	118.9
C71—C61—H61	120.4	C72—C62—H62	121.2
C61—C71—C81	120.15 (17)	C62—C72—C82	120.24 (16)
C61—C71—H71	118.1	C62—C72—H72	119.8
C81—C71—H71	121.7	C82—C72—H72	119.9
C71—C81—C91	119.74 (16)	C72—C82—C92	119.94 (15)
C71—C81—H81	119.3	C72—C82—H82	119.8
C91—C81—H81	120.9	C92—C82—H82	120.2
C41—C91—C81	121.45 (16)	C42—C92—C82	120.85 (16)
C41—C91—H91	117.5	C42—C92—H92	119.1
C81—C91—H91	121.0	C82—C92—H92	120.0

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O11—H11···O52ⁱ	0.81 (2)	2.01 (2)	2.8137 (17)	176 (2)
O12—H12···O51ⁱⁱ	0.87 (2)	1.99 (2)	2.7945 (18)	155 (2)
O51—H51···N21	0.86 (2)	1.85 (2)	2.6384 (18)	152 (2)
O52—H52···N22	0.85 (2)	1.84 (2)	2.6285 (18)	153 (2)

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

Acknowledgements

The authors thank the EPSRC and the Cambridge Crystallographic Data Centre for funding.

References

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Volume 62| Part 9| September 2006| Pages o3944-o3946

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

Salicylaldoxime-III at 150 K

Comment

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds