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

Slassi, S.; Stetsiuk, O.; Amine, A.; Aarjane, M.; El-Ghayoury, A.; Zouihri, H.; Yamni, K.

doi:10.1107/S2414314619000361

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 4| Part 1| January 2019| x190036

https://doi.org/10.1107/S2414314619000361

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

Siham Slassi,^a Oleh Stetsiuk,^b Amina Amine,^a Mohammed Aarjane,^a Abdelkrim El-Ghayoury,^b Hafid Zouihri ^c and Khalid Yamni ^c ^*

^aLCBAE, Equipe Chimie Moléculaire et Molécules Bioactives, Université Moulay Ismail, Faculté des Sciences, Meknès, Morocco, ^bUniversité d Angers, CNRS UMR 6200, Laboratoire MOLTECH-Anjou, 2 bd Lavoisier, 49045 Angers Cedex, France, and ^cLaboratoire 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 W. T. A. Harrison, University of Aberdeen, Scotland (Received 3 January 2019; accepted 7 January 2019; online 11 January 2019)

In the title compound, C₂₀H₂₁N₅O, the dihedral angles between the central phenol ring and pendant toluyl and imidazole rings are 3.20 (16) and 81.44 (14)°, respectively; the dihedral angle between the pendant rings is 84.39 (16)°. An intramolecular O—H⋯N hydrogen bond occurs. A Hirshfeld fingerprint analysis indicates that H⋯H contacts account for 48.6% of the surface.

Keywords: crystal structure; hydrogen bonding; offset H⋯H interactions; Hirshfeld surface analysis.

CCDC reference: 1889270

Structure description

As a continuation of our studies of compounds based on azo Schiff base derivatives (Slassi et al., 2017 ), we report herein the synthesis and structure of the title compound.

The molecular structure of the title compound is shown in Fig. 1. The bond lengths and angles of the imidazol moiety are comparable with those reported for similar compounds (Slassi et al., 2017). The dihedral angles between the phenol ring and pendant toluyl and imidazole rings are 3.20 (16) and 81.44 (14)°, respectively; the dihedral angle between the pendant rings is 84.39 (16)°. The N1—N2 and N3—C14 bond lengths [1.174 (4) and 1.272 (4) Å, respectively] confirm their double-bond character, whereas the N4—C18 and N4—C19 values [1.347 (3) and 1.370 (3) Å, respectively] are shorter than (nominal) isolated C—N bonds (1.46 Å) due to conjugation. An intramolecular O—H⋯N hydrogen bond occurs (Table 1) but no directional interactions beyond van der Waals' contacts could be identified in the packing (Fig. 2).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N3	0.82	1.86	2.588 (3)	148

Figure 1
The molecular structure with displacement ellipsoids drawn at the 30% probability level.

Figure 2
The packing viewed down [010].

Two-dimensional Hirshfeld fingerprint plots (McKinnon et al., 2007 ) indicate that 48.6% of the surface is due to H⋯H contacts, followed by C⋯H, N⋯H and O⋯H interactions, which contribute 28.5, 15.2 and 6.1%, respectively.

Synthesis and crystallization

A diazonium-salt solution was prepared by dissolving p-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, 0.010 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 solution. N-(3-Aminopropyl)imidazole (4.0 mmol) was added into a methanol solution (30 ml) of 2-hydroxy-5-(p-tolyldiazenyl)benzaldehyde (4.0 mmol) prepared in the first step of the reaction. The mixture was refluxed for 2 h and cooled to room temperature. The solvent was removed on a rotatory evaporator and the orange product was rinsed and recrystallized from mixed solvents of methanol and ether to give orange crystals after one week.

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	Monoclinic, P2/n
Temperature (K)	293
a, b, c (Å)	12.2410 (4), 5.9386 (2), 25.2112 (9)
β (°)	90.317 (3)
V (Å³)	1832.69 (11)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	0.65
Crystal size (mm)	0.35 × 0.22 × 0.13

Data collection
Diffractometer	Agilent SuperNova CCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	5548, 3487, 3037
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.622

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.084, 0.245, 1.08
No. of reflections	3487
No. of parameters	236
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.02, −0.68
Computer programs: APEX2 and SAINT (Bruker, 2009 ), SHELXT (Sheldrick, 2015a ), SHELXL2014 (Sheldrick, 2015b ), PLATON (Spek, 2009 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 1889270

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314619000361/hb4279sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314619000361/hb4279Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314619000361/hb4279Isup3.cml

checkCIF report

Computing details top

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

(I) top

Crystal data top

C₂₀H₂₁N₅O	F(000) = 736
M_r = 347.42	D_x = 1.259 Mg m⁻³
Monoclinic, P2/n	Cu Kα radiation, λ = 1.54184 Å
a = 12.2410 (4) Å	Cell parameters from 235 reflections
b = 5.9386 (2) Å	θ = 0.7–32.0°
c = 25.2112 (9) Å	µ = 0.65 mm⁻¹
β = 90.317 (3)°	T = 293 K
V = 1832.69 (11) Å³	Prism, orange
Z = 4	0.35 × 0.22 × 0.13 mm

Data collection top

Agilent SuperNova CCD diffractometer	R_int = 0.016
Radiation source: fine-focus sealed tube	θ_max = 73.5°, θ_min = 4.0°
ω and φ scans	h = −14→14
5548 measured reflections	k = −4→7
3487 independent reflections	l = −30→25
3037 reflections with I > 2σ(I)

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.084	w = 1/[σ²(F_o²) + (0.1176P)² + 1.9097P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.245	(Δ/σ)_max < 0.001
S = 1.08	Δρ_max = 1.02 e Å⁻³
3487 reflections	Δρ_min = −0.67 e Å⁻³
236 parameters	Extinction correction: SHELXL2014/7 (Sheldrick 2014, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0012 (6)
Primary atom site location: dual

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.

Refinement. Hydrogen atoms were placed in calculated positions and treated as riding: (O—H = 0.82 Å, N—H = and C—H = 0.93 to 0.97 Å) and refined using a riding model, with U_iso(H) = 1.2Ueq(C) and 1.5Ueq(O).

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

	x	y	z	U_iso*/U_eq
C13	0.8079 (4)	0.4904 (8)	0.15663 (17)	0.0903 (14)
H13A	0.7426	0.5753	0.1499	0.135*
H13B	0.8425	0.4547	0.1236	0.135*
H13C	0.7897	0.3537	0.1749	0.135*
C14	1.4876 (2)	1.0267 (5)	0.40967 (12)	0.0478 (7)
H14	1.5059	0.8854	0.3965	0.057*
C15	1.6512 (2)	1.0082 (5)	0.45962 (14)	0.0530 (8)
H15A	1.6768	0.9101	0.4315	0.064*
H15B	1.6357	0.9160	0.4904	0.064*
C16	1.7384 (2)	1.1766 (5)	0.47322 (12)	0.0463 (7)
H16A	1.7086	1.2866	0.4976	0.056*
H16B	1.7595	1.2556	0.4412	0.056*
C17	1.8392 (2)	1.0701 (5)	0.49814 (12)	0.0495 (7)
H17A	1.8915	1.1870	0.5070	0.059*
H17B	1.8189	0.9943	0.5307	0.059*
C18	1.8979 (2)	0.6838 (4)	0.46977 (10)	0.0405 (6)
H18	1.8738	0.6112	0.5002	0.049*
C19	1.9335 (2)	0.9502 (5)	0.41319 (11)	0.0476 (7)
H19	1.9400	1.0892	0.3965	0.057*
C20	1.9650 (2)	0.7472 (5)	0.39414 (11)	0.0501 (7)
H20	1.9972	0.7252	0.3612	0.060*
N3	1.55155 (17)	1.1238 (4)	0.44235 (11)	0.0484 (6)
N4	1.89023 (16)	0.9079 (4)	0.46217 (8)	0.0380 (5)
N6	1.9431 (2)	0.5788 (4)	0.42948 (9)	0.0468 (6)
O1	1.42088 (16)	1.4663 (3)	0.44393 (9)	0.0535 (6)
H1	1.4761	1.3929	0.4505	0.080*
C1	0.9844 (3)	0.5444 (6)	0.20574 (12)	0.0658 (9)
H2	1.0071	0.4026	0.1947	0.079*
C2	0.8845 (3)	0.6273 (6)	0.19032 (12)	0.0644 (9)
C3	0.8533 (4)	0.8425 (7)	0.20665 (14)	0.0763 (11)
H3	0.7858	0.8970	0.1954	0.092*
C4	0.9149 (4)	0.9741 (8)	0.23747 (15)	0.0763 (11)
H4	0.8913	1.1168	0.2474	0.092*
C5	1.0114 (4)	0.8946 (6)	0.25356 (12)	0.0703 (11)
C6	1.0528 (3)	0.6788 (8)	0.23901 (13)	0.0785 (12)
H6	1.1208	0.6285	0.2506	0.094*
C7	1.3171 (2)	1.0200 (5)	0.35781 (11)	0.0489 (7)
H7	1.3370	0.8779	0.3457	0.059*
C8	1.2196 (2)	1.1128 (6)	0.34087 (11)	0.0520 (7)
C9	1.1896 (2)	1.3256 (6)	0.35955 (12)	0.0556 (8)
H9	1.1237	1.3890	0.3486	0.067*
C10	1.2569 (2)	1.4428 (5)	0.39417 (12)	0.0511 (7)
H10	1.2358	1.5839	0.4065	0.061*
C11	1.3862 (2)	1.1332 (5)	0.39245 (11)	0.0433 (6)
C12	1.3566 (2)	1.3504 (5)	0.41079 (11)	0.0450 (6)
N1	1.0795 (3)	1.0496 (5)	0.28969 (13)	0.0807 (11)
N2	1.1576 (2)	0.9503 (6)	0.30336 (11)	0.0681 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C13	0.116 (4)	0.081 (3)	0.074 (2)	0.007 (3)	−0.042 (2)	−0.015 (2)
C14	0.0355 (13)	0.0398 (14)	0.0683 (18)	0.0006 (11)	0.0102 (12)	−0.0050 (13)
C15	0.0353 (14)	0.0440 (15)	0.080 (2)	0.0054 (12)	0.0043 (13)	0.0064 (14)
C16	0.0420 (14)	0.0410 (14)	0.0557 (16)	0.0095 (11)	−0.0084 (12)	−0.0055 (12)
C17	0.0467 (15)	0.0449 (15)	0.0568 (16)	0.0099 (12)	−0.0092 (12)	−0.0075 (13)
C18	0.0407 (13)	0.0396 (13)	0.0411 (13)	0.0024 (10)	0.0025 (10)	0.0091 (10)
C19	0.0426 (14)	0.0500 (16)	0.0503 (15)	0.0007 (12)	0.0023 (11)	0.0206 (13)
C20	0.0462 (15)	0.0629 (18)	0.0412 (14)	0.0048 (13)	0.0065 (11)	0.0100 (13)
N3	0.0309 (11)	0.0414 (12)	0.0728 (15)	0.0034 (9)	0.0024 (10)	−0.0025 (11)
N4	0.0321 (10)	0.0372 (11)	0.0447 (11)	0.0030 (8)	−0.0030 (8)	0.0064 (9)
N6	0.0483 (13)	0.0435 (13)	0.0486 (13)	0.0037 (10)	0.0030 (10)	0.0032 (10)
O1	0.0425 (10)	0.0406 (11)	0.0772 (14)	0.0046 (8)	−0.0049 (9)	−0.0094 (10)
C1	0.091 (3)	0.067 (2)	0.0394 (15)	−0.0114 (19)	−0.0074 (15)	0.0012 (14)
C2	0.089 (2)	0.065 (2)	0.0395 (15)	−0.0021 (18)	−0.0112 (15)	−0.0008 (14)
C3	0.109 (3)	0.068 (2)	0.0517 (19)	−0.005 (2)	0.0041 (19)	−0.0053 (17)
C4	0.095 (3)	0.074 (2)	0.060 (2)	−0.004 (2)	0.005 (2)	−0.0018 (19)
C5	0.118 (3)	0.058 (2)	0.0353 (15)	−0.033 (2)	0.0192 (17)	−0.0083 (14)
C6	0.074 (2)	0.121 (3)	0.0412 (16)	−0.019 (2)	−0.0011 (15)	0.032 (2)
C7	0.0419 (14)	0.0543 (16)	0.0507 (15)	−0.0049 (12)	0.0113 (12)	−0.0046 (13)
C8	0.0432 (15)	0.0693 (19)	0.0436 (14)	−0.0089 (14)	0.0083 (11)	0.0039 (14)
C9	0.0393 (14)	0.077 (2)	0.0506 (16)	0.0053 (14)	0.0014 (12)	0.0181 (15)
C10	0.0449 (15)	0.0520 (16)	0.0566 (17)	0.0102 (13)	0.0075 (12)	0.0098 (13)
C11	0.0327 (12)	0.0440 (14)	0.0532 (15)	−0.0010 (10)	0.0075 (11)	−0.0006 (12)
C12	0.0370 (13)	0.0450 (15)	0.0531 (15)	0.0013 (11)	0.0055 (11)	0.0044 (12)
N1	0.106 (3)	0.0599 (18)	0.076 (2)	0.0242 (18)	0.0444 (19)	0.0206 (16)
N2	0.0388 (13)	0.099 (2)	0.0666 (17)	0.0065 (14)	0.0089 (12)	0.0411 (16)

Geometric parameters (Å, º) top

C13—C2	1.501 (5)	O1—C12	1.336 (3)
C13—H13A	0.9600	O1—H1	0.8200
C13—H13B	0.9600	C1—C2	1.372 (5)
C13—H13C	0.9600	C1—C6	1.427 (5)
C14—N3	1.272 (4)	C1—H2	0.9300
C14—C11	1.457 (4)	C2—C3	1.397 (5)
C14—H14	0.9300	C3—C4	1.333 (6)
C15—N3	1.464 (3)	C3—H3	0.9300
C15—C16	1.500 (4)	C4—C5	1.333 (6)
C15—H15A	0.9700	C4—H4	0.9300
C15—H15B	0.9700	C5—C6	1.426 (6)
C16—C17	1.520 (4)	C5—N1	1.537 (5)
C16—H16A	0.9700	C6—H6	0.9300
C16—H16B	0.9700	C7—C8	1.381 (4)
C17—N4	1.465 (3)	C7—C11	1.386 (4)
C17—H17A	0.9700	C7—H7	0.9300
C17—H17B	0.9700	C8—C9	1.399 (5)
C18—N6	1.317 (3)	C8—N2	1.547 (5)
C18—N4	1.347 (3)	C9—C10	1.385 (5)
C18—H18	0.9300	C9—H9	0.9300
C19—C20	1.354 (4)	C10—C12	1.401 (4)
C19—N4	1.370 (3)	C10—H10	0.9300
C19—H19	0.9300	C11—C12	1.417 (4)
C20—N6	1.367 (4)	N1—N2	1.174 (4)
C20—H20	0.9300

C2—C13—H13A	109.5	C18—N6—C20	103.9 (2)
C2—C13—H13B	109.5	C12—O1—H1	109.5
H13A—C13—H13B	109.5	C2—C1—C6	119.0 (4)
C2—C13—H13C	109.5	C2—C1—H2	120.5
H13A—C13—H13C	109.5	C6—C1—H2	120.5
H13B—C13—H13C	109.5	C1—C2—C3	119.3 (4)
N3—C14—C11	121.1 (3)	C1—C2—C13	121.2 (4)
N3—C14—H14	119.5	C3—C2—C13	119.4 (4)
C11—C14—H14	119.5	C4—C3—C2	123.6 (4)
N3—C15—C16	110.2 (2)	C4—C3—H3	118.2
N3—C15—H15A	109.6	C2—C3—H3	118.2
C16—C15—H15A	109.6	C3—C4—C5	117.8 (4)
N3—C15—H15B	109.6	C3—C4—H4	121.1
C16—C15—H15B	109.6	C5—C4—H4	121.1
H15A—C15—H15B	108.1	C4—C5—C6	123.7 (4)
C15—C16—C17	113.1 (2)	C4—C5—N1	116.4 (4)
C15—C16—H16A	109.0	C6—C5—N1	119.9 (4)
C17—C16—H16A	109.0	C5—C6—C1	116.5 (4)
C15—C16—H16B	109.0	C5—C6—H6	121.8
C17—C16—H16B	109.0	C1—C6—H6	121.8
H16A—C16—H16B	107.8	C8—C7—C11	121.6 (3)
N4—C17—C16	111.5 (2)	C8—C7—H7	119.2
N4—C17—H17A	109.3	C11—C7—H7	119.2
C16—C17—H17A	109.3	C7—C8—C9	119.0 (3)
N4—C17—H17B	109.3	C7—C8—N2	111.1 (3)
C16—C17—H17B	109.3	C9—C8—N2	129.8 (3)
H17A—C17—H17B	108.0	C10—C9—C8	120.7 (3)
N6—C18—N4	112.8 (2)	C10—C9—H9	119.7
N6—C18—H18	123.6	C8—C9—H9	119.7
N4—C18—H18	123.6	C9—C10—C12	120.4 (3)
C20—C19—N4	105.6 (2)	C9—C10—H10	119.8
C20—C19—H19	127.2	C12—C10—H10	119.8
N4—C19—H19	127.2	C7—C11—C12	119.4 (3)
C19—C20—N6	111.3 (2)	C7—C11—C14	119.5 (3)
C19—C20—H20	124.4	C12—C11—C14	121.1 (3)
N6—C20—H20	124.4	O1—C12—C10	119.6 (3)
C14—N3—C15	119.3 (3)	O1—C12—C11	121.5 (2)
C18—N4—C19	106.4 (2)	C10—C12—C11	118.9 (3)
C18—N4—C17	126.2 (2)	N2—N1—C5	108.1 (3)
C19—N4—C17	127.3 (2)	N1—N2—C8	105.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N3	0.82	1.86	2.588 (3)	148

References

Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
McKinnon, J. J., Jayatilaka, D. & Spackman, M. A. (2007). Chem. Commun. pp. 3814–3816. Web of Science CrossRef 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
Slassi, S., Aarjane, M., Amine, A., Zouihri, H. & Yamni, K. (2017). IUCrData, 2, x171477. 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

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