2-((E)-{[3-(1H-Imidazol-1-yl)prop­yl]imino}­meth­yl)-4-[(E)-(2-methyl­phen­yl)diazen­yl]phenol

Slassi, S.; Aarjane, M.; Amine, A.; Zouihri, H.; Yamni, K.

doi:10.1107/S2414314617014778

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 10| October 2017| x171477

https://doi.org/10.1107/S2414314617014778

Open

access

2-((E)-{[3-(1H-Imidazol-1-yl)propyl]imino}methyl)-4-[(E)-(2-methylphenyl)diazenyl]phenol

Siham Slassi,^a Mohammed Aarjane,^a Amina Amine,^a Hafid Zouihri ^b and Khalid Yamni ^b ^*

^aLCBAE, Equipe Chimie Moléculaire et Molécules Bioactives, Université Moulay Ismail, Faculté des Sciences, Meknès, Morocco, and ^bLaboratoire de Chimie des Matériaux et Biotechnologie des Produits Naturels, E.Ma.Me.P.S., Université Moulay Ismail, Faculté des Sciences, Meknès, Morocco
^*Correspondence e-mail: kyamni@hotmail.com

Edited by J. Simpson, University of Otago, New Zealand (Received 5 October 2017; accepted 12 October 2017; online 20 October 2017)

In the title compound, C₂₀H₂₁N₅O, an intramolecular O—H⋯N hydrogen bond forms between the –OH substituent of the phenol ring and the adjacent iminomethyl N atom, enclosing an S6 ring. The dihedral angles between the imidazole ring and the methylphenyl and phenol rings are 86.93 (14) and 88.00 (13)°, respectively, while that between the methylphenyl and phenol rings is 2.18 (12)°.

Keywords: crystal structure; imidazole; phenol; intramolecular hydrogen bond.

CCDC reference: 1579590

Structure description

In the title compound (Fig. 1), an S6 ring motif is formed by an intramolecular O1—H1⋯N3 hydrogen bond (Table 1). The dihedral angles between the imidazole ring and the methylphenyl and phenol rings are 86.93 (14) and 88.00 (13)°, respectively. In contrast, the methylphenyldiazenylphenol segment of the molecule is almost planar, with a dihedral angle of 2.18 (12)° between the C1–C6 and C7–C12 benzene rings.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N3	0.82	1.80	2.534 (2)	148

Figure 1
The structure of the title compound, showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres with arbitrary radii.

Synthesis and crystallization

A diazonium salt solution was prepared by dissolving o-toluidine amine (1.23 g, 0.01 mol) in a mixture of water and concentrated hydrochloric acid (8 and 3 ml, respectively). The resulting solution was cooled to 273 K, treated with aqueous (1.0 M) sodium nitrate (15 ml) dropwise and stirred for 15 min. Salicylaldehyde (2.2 g, 0.01 mol) was dissolved in 10% sodium hydroxide (50 ml). The diazonium solution was then added dropwise to initiate the coupling reaction. After the mixture had been stirred for 1 h at 273–278 K, the precipitate was filtered off. Crystals were obtained by recrystallization from ethanol. N-(3-Aminopropyl)imidazole (0.5 g, 4 mmol) was next added to an ethanol solution (30 ml) of 2-hydroxy-5-(o-tolyldiazenyl)benzaldehyde (0.96 g, 4 mmol). The mixture was refluxed for 2 h and cooled to room temperature. The solvent was removed under vacuum. The final product obtained after extraction was recrystallized from a mixture of ethanol and diethyl ether, the solution being allowed to evaporate slowly at a constant ambient temperature to give coulourless good-quality crystals after 3 d.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₀H₂₁N₅O
M_r	347.42
Crystal system, space group	Orthorhombic, P2₁2₁2
Temperature (K)	293
a, b, c (Å)	9.7570 (3), 32.0691 (13), 5.8643 (2)
V (Å³)	1834.93 (11)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.08
Crystal size (mm)	0.25 × 0.15 × 0.12

Data collection
Diffractometer	Bruker APEXII CCD detector
No. of measured, independent and observed [I > 2σ(I)] reflections	25352, 3590, 2978
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.105, 1.04
No. of reflections	3590
No. of parameters	238
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.16
Absolute structure	Flack x determined using 1099 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter	−0.4 (4)
Computer programs: APEX2 and SAINT (Bruker, 2005 ), SHELXS97 (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ), PLATON (Spek, 2009 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 1579590

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314617014778/sj4139sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617014778/sj4139Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617014778/sj4139Isup3.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

2-((E)-{[3-(1H-Imidazol-1-yl)propyl]imino}methyl)-4-[(E)-(2-methylphenyl)diazenyl]phenol top

Crystal data top

C₂₀H₂₁N₅O	D_x = 1.258 Mg m⁻³
M_r = 347.42	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2	Cell parameters from 245 reflections
a = 9.7570 (3) Å	θ = 0.2–52°
b = 32.0691 (13) Å	µ = 0.08 mm⁻¹
c = 5.8643 (2) Å	T = 293 K
V = 1834.93 (11) Å³	Prism, colourless
Z = 4	0.25 × 0.15 × 0.12 mm
F(000) = 736

Data collection top

Bruker APEXII CCD detector diffractometer	2978 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.026
Graphite monochromator	θ_max = 26.0°, θ_min = 1.3°
ω and φ scans	h = −12→11
25352 measured reflections	k = −39→39
3590 independent reflections	l = −7→7

Refinement top

Refinement on F²	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ²(F_o²) + (0.0669P)² + 0.0698P] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.037	(Δ/σ)_max < 0.001
wR(F²) = 0.105	Δρ_max = 0.18 e Å⁻³
S = 1.04	Δρ_min = −0.16 e Å⁻³
3590 reflections	Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
238 parameters	Extinction coefficient: 0.011 (3)
0 restraints	Absolute structure: Flack x determined using 1099 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Hydrogen site location: inferred from neighbouring sites	Absolute structure parameter: −0.4 (4)

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
C12	0.3769 (2)	0.07393 (7)	0.3773 (4)	0.0467 (5)
H12	0.4141	0.0641	0.2415	0.056*
O1	0.41943 (18)	0.15905 (5)	0.7861 (3)	0.0678 (5)
H1	0.4841	0.1685	0.7134	0.102*
C11	0.4278 (2)	0.11065 (6)	0.4741 (4)	0.0418 (5)
C13	0.5404 (2)	0.13322 (7)	0.3685 (4)	0.0469 (5)
H13	0.5787	0.1233	0.2339	0.056*
N1	0.26508 (19)	−0.00103 (6)	0.2286 (3)	0.0531 (5)
N3	0.58696 (18)	0.16637 (5)	0.4584 (3)	0.0494 (5)
C8	0.2161 (2)	0.06705 (7)	0.6845 (4)	0.0555 (6)
H8	0.1450	0.0525	0.7539	0.067*
N2	0.2132 (2)	0.01415 (6)	0.4030 (3)	0.0541 (5)
C6	0.2023 (2)	−0.03952 (7)	0.1584 (4)	0.0489 (5)
C14	0.7004 (2)	0.18966 (7)	0.3569 (4)	0.0503 (6)
H14A	0.6653	0.2138	0.2761	0.060*
H14B	0.7487	0.1722	0.2484	0.060*
C9	0.2645 (2)	0.10291 (7)	0.7834 (4)	0.0563 (6)
H9	0.2260	0.1125	0.9186	0.068*
C7	0.2719 (2)	0.05208 (7)	0.4815 (4)	0.0471 (5)
C1	0.2536 (2)	−0.05815 (7)	−0.0377 (4)	0.0507 (6)
C5	0.0958 (3)	−0.05797 (8)	0.2794 (5)	0.0662 (7)
H5	0.0629	−0.0454	0.4115	0.079*
N4	0.99745 (18)	0.22455 (5)	0.3059 (3)	0.0441 (4)
C10	0.3715 (2)	0.12496 (6)	0.6814 (4)	0.0478 (5)
C17	1.1092 (2)	0.20035 (7)	0.3481 (4)	0.0542 (6)
H17	1.1344	0.1885	0.4866	0.065*
C20	0.3712 (3)	−0.03963 (9)	−0.1689 (5)	0.0686 (7)
H20A	0.3643	−0.0098	−0.1669	0.103*
H20B	0.3684	−0.0494	−0.3236	0.103*
H20C	0.4562	−0.0480	−0.0998	0.103*
C3	0.0873 (3)	−0.11327 (8)	0.0100 (6)	0.0672 (7)
H3	0.0485	−0.1380	−0.0415	0.081*
C16	0.8941 (2)	0.23810 (7)	0.4694 (4)	0.0552 (6)
H16A	0.8410	0.2605	0.4022	0.066*
H16B	0.9397	0.2491	0.6034	0.066*
C19	1.1760 (3)	0.19709 (8)	0.1467 (5)	0.0622 (7)
H19	1.2566	0.1822	0.1248	0.075*
C18	1.0022 (3)	0.23486 (8)	0.0844 (4)	0.0596 (6)
H18	0.9374	0.2516	0.0123	0.072*
C15	0.7975 (2)	0.20352 (7)	0.5421 (4)	0.0538 (6)
H15A	0.8512	0.1797	0.5914	0.065*
H15B	0.7443	0.2131	0.6718	0.065*
N5	1.1094 (2)	0.21854 (8)	−0.0191 (4)	0.0712 (6)
C4	0.0388 (3)	−0.09479 (8)	0.2045 (6)	0.0714 (8)
H4	−0.0325	−0.1071	0.2857	0.086*
C2	0.1933 (3)	−0.09525 (7)	−0.1093 (5)	0.0618 (7)
H2	0.2254	−0.1082	−0.2408	0.074*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C12	0.0489 (11)	0.0477 (11)	0.0437 (11)	0.0006 (10)	−0.0008 (10)	−0.0074 (10)
O1	0.0660 (11)	0.0584 (10)	0.0792 (12)	−0.0179 (8)	0.0269 (10)	−0.0315 (9)
C11	0.0404 (11)	0.0399 (10)	0.0451 (11)	0.0019 (8)	0.0003 (9)	−0.0026 (9)
C13	0.0470 (12)	0.0482 (11)	0.0456 (11)	0.0012 (10)	0.0048 (10)	−0.0057 (10)
N1	0.0543 (11)	0.0472 (10)	0.0579 (11)	−0.0060 (9)	−0.0022 (9)	−0.0101 (9)
N3	0.0454 (10)	0.0446 (10)	0.0581 (11)	−0.0036 (8)	0.0082 (9)	−0.0046 (8)
C8	0.0496 (12)	0.0528 (13)	0.0641 (15)	−0.0096 (11)	0.0106 (13)	−0.0070 (11)
N2	0.0536 (10)	0.0492 (11)	0.0595 (12)	−0.0063 (9)	−0.0010 (10)	−0.0111 (9)
C6	0.0450 (11)	0.0439 (11)	0.0577 (14)	−0.0012 (10)	−0.0072 (11)	−0.0080 (10)
C14	0.0494 (12)	0.0492 (12)	0.0524 (13)	−0.0049 (10)	0.0098 (11)	−0.0001 (10)
C9	0.0542 (14)	0.0571 (14)	0.0577 (14)	−0.0081 (11)	0.0152 (12)	−0.0164 (11)
C7	0.0454 (11)	0.0441 (11)	0.0517 (12)	−0.0043 (10)	−0.0044 (11)	−0.0041 (10)
C1	0.0504 (12)	0.0459 (11)	0.0557 (13)	0.0054 (10)	−0.0091 (11)	−0.0050 (10)
C5	0.0625 (14)	0.0585 (14)	0.0775 (18)	−0.0102 (12)	0.0078 (15)	−0.0180 (13)
N4	0.0449 (9)	0.0440 (9)	0.0435 (9)	−0.0058 (8)	0.0065 (9)	−0.0005 (8)
C10	0.0427 (11)	0.0439 (12)	0.0568 (13)	−0.0009 (9)	0.0031 (11)	−0.0103 (10)
C17	0.0508 (12)	0.0512 (12)	0.0606 (14)	−0.0055 (11)	−0.0064 (12)	0.0033 (11)
C20	0.0768 (17)	0.0621 (15)	0.0668 (16)	0.0011 (13)	0.0108 (15)	−0.0055 (13)
C3	0.0579 (14)	0.0482 (13)	0.096 (2)	−0.0028 (12)	−0.0175 (16)	−0.0191 (14)
C16	0.0547 (13)	0.0569 (14)	0.0539 (13)	−0.0120 (11)	0.0166 (12)	−0.0108 (11)
C19	0.0528 (13)	0.0512 (13)	0.0827 (19)	−0.0042 (11)	0.0115 (14)	−0.0136 (13)
C18	0.0678 (15)	0.0632 (15)	0.0480 (13)	0.0051 (13)	0.0092 (13)	0.0098 (11)
C15	0.0531 (12)	0.0587 (14)	0.0496 (13)	−0.0088 (11)	0.0104 (11)	0.0029 (11)
N5	0.0828 (15)	0.0772 (14)	0.0535 (12)	−0.0035 (13)	0.0235 (13)	−0.0049 (11)
C4	0.0605 (15)	0.0572 (15)	0.097 (2)	−0.0141 (12)	0.0049 (15)	−0.0138 (15)
C2	0.0670 (15)	0.0505 (13)	0.0679 (17)	0.0053 (12)	−0.0091 (14)	−0.0165 (12)

Geometric parameters (Å, º) top

C12—C7	1.383 (3)	C5—C4	1.377 (3)
C12—C11	1.398 (3)	C5—H5	0.9300
C12—H12	0.9300	N4—C18	1.341 (3)
O1—C10	1.338 (3)	N4—C17	1.361 (3)
O1—H1	0.8200	N4—C16	1.458 (3)
C11—C10	1.410 (3)	C17—C19	1.353 (4)
C11—C13	1.454 (3)	C17—H17	0.9300
C13—N3	1.271 (3)	C20—H20A	0.9600
C13—H13	0.9300	C20—H20B	0.9600
N1—N2	1.240 (3)	C20—H20C	0.9600
N1—C6	1.439 (3)	C3—C4	1.370 (4)
N3—C14	1.462 (3)	C3—C2	1.376 (4)
C8—C9	1.372 (3)	C3—H3	0.9300
C8—C7	1.395 (3)	C16—C15	1.517 (3)
C8—H8	0.9300	C16—H16A	0.9700
N2—C7	1.421 (3)	C16—H16B	0.9700
C6—C1	1.389 (3)	C19—N5	1.357 (4)
C6—C5	1.390 (3)	C19—H19	0.9300
C14—C15	1.508 (3)	C18—N5	1.317 (3)
C14—H14A	0.9700	C18—H18	0.9300
C14—H14B	0.9700	C15—H15A	0.9700
C9—C10	1.396 (3)	C15—H15B	0.9700
C9—H9	0.9300	C4—H4	0.9300
C1—C2	1.392 (3)	C2—H2	0.9300
C1—C20	1.504 (4)

C7—C12—C11	120.7 (2)	O1—C10—C9	118.6 (2)
C7—C12—H12	119.7	O1—C10—C11	121.68 (19)
C11—C12—H12	119.7	C9—C10—C11	119.74 (19)
C10—O1—H1	109.5	C19—C17—N4	105.7 (2)
C12—C11—C10	119.04 (19)	C19—C17—H17	127.1
C12—C11—C13	120.97 (19)	N4—C17—H17	127.1
C10—C11—C13	119.95 (19)	C1—C20—H20A	109.5
N3—C13—C11	120.7 (2)	C1—C20—H20B	109.5
N3—C13—H13	119.7	H20A—C20—H20B	109.5
C11—C13—H13	119.7	C1—C20—H20C	109.5
N2—N1—C6	113.5 (2)	H20A—C20—H20C	109.5
C13—N3—C14	121.94 (19)	H20B—C20—H20C	109.5
C9—C8—C7	121.0 (2)	C4—C3—C2	120.1 (2)
C9—C8—H8	119.5	C4—C3—H3	120.0
C7—C8—H8	119.5	C2—C3—H3	120.0
N1—N2—C7	115.98 (19)	N4—C16—C15	113.40 (19)
C1—C6—C5	120.6 (2)	N4—C16—H16A	108.9
C1—C6—N1	116.9 (2)	C15—C16—H16A	108.9
C5—C6—N1	122.5 (2)	N4—C16—H16B	108.9
N3—C14—C15	109.41 (19)	C15—C16—H16B	108.9
N3—C14—H14A	109.8	H16A—C16—H16B	107.7
C15—C14—H14A	109.8	C17—C19—N5	110.8 (2)
N3—C14—H14B	109.8	C17—C19—H19	124.6
C15—C14—H14B	109.8	N5—C19—H19	124.6
H14A—C14—H14B	108.2	N5—C18—N4	112.1 (3)
C8—C9—C10	120.1 (2)	N5—C18—H18	124.0
C8—C9—H9	120.0	N4—C18—H18	124.0
C10—C9—H9	120.0	C14—C15—C16	113.8 (2)
C12—C7—C8	119.5 (2)	C14—C15—H15A	108.8
C12—C7—N2	126.1 (2)	C16—C15—H15A	108.8
C8—C7—N2	114.4 (2)	C14—C15—H15B	108.8
C6—C1—C2	117.7 (2)	C16—C15—H15B	108.8
C6—C1—C20	121.9 (2)	H15A—C15—H15B	107.7
C2—C1—C20	120.4 (2)	C18—N5—C19	104.6 (2)
C4—C5—C6	120.2 (3)	C3—C4—C5	119.8 (3)
C4—C5—H5	119.9	C3—C4—H4	120.1
C6—C5—H5	119.9	C5—C4—H4	120.1
C18—N4—C17	106.8 (2)	C3—C2—C1	121.6 (2)
C18—N4—C16	126.0 (2)	C3—C2—H2	119.2
C17—N4—C16	127.2 (2)	C1—C2—H2	119.2

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N3	0.82	1.80	2.534 (2)	148

References

Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249–259. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.