Crystal structure of (E)-3-[(2,6-di­methyl­phen­yl)diazen­yl]-7-methyl-1H-indazole

Yagi, S.; Haraguchi, T.; Akitsu, T.

doi:10.1107/S2056989018012483

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ISSN: 2056-9890

Volume 74| Part 10| October 2018| Pages 1421-1423

https://doi.org/10.1107/S2056989018012483

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Crystal structure of (E)-3-[(2,6-dimethylphenyl)diazenyl]-7-methyl-1H-indazole

Shiomi Yagi,^a Tomoyuki Haraguchi ^a and Takashiro Akitsu ^a ^*

^aDepartment of Chemistry, Faculty of Science, Tokyo University of Science, 1-3 Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan
^*Correspondence e-mail: akitsu@rs.kagu.tus.ac.jp

Edited by E. V. Boldyreva, Russian Academy of Sciences, Russia (Received 11 July 2018; accepted 4 September 2018; online 14 September 2018)

The title azo compound, C₁₆H₁₆N₄, was synthesized from 2,6-dimethylaniline. The diazenyl group adopts a trans (E) conformation, with an N=N bond length of 1.265 (4) Å. The pyrazole ring is approximately planar. In the crystal, zigzag chains along the b-axis direction with a C(3) is graph-set motif are formed by N—H⋯N hydrogen bonds involving the pyrazole moiety.

Keywords: crystal structure; photochromism; azo benzene; pyrazole; indazole; chiral crystallization.

CCDC reference: 1865810

1. Chemical context

Azobenzene derivatives are known to be photochromic compounds and numerous studies have been reported (Aritake et al., 2011 ; Bobrovsky et al., 2016 ; Li et al., 2017 ). As an example of this, our group has reported the crystal structures of several azobenzene derivatives (Moriwaki & Akitsu, 2015 ; Moriwaki et al., 2017 ).

Pyrazole is an aromatic compound comprising a five-membered ring with two adjacent N atoms. Pyrazole derivatives are biologically active and have attracted attention for the synthesis of new medicinal products (Ansari et al., 2017 ).

Here we report the crystal structure of (E)-3-[(2,6-dimethylphenyl)diazenyl]-7-methyl-1H-indazole, which has an azobenzene moiety and a pyrazole moiety (Fig. 1).

Figure 1
The structure of the title compound shown with 50% probability displacement ellipsoids.

2. Structural commentary

The molecular structure of the title compound is composed of a benzene ring linked to an indazole unit by an N=N bond. In the azobenzene moiety, the azo N=N double bond adopts an E configuration, with an N=N bond length of 1.265 (4) Å and a corresponding C9—N3—N4—C15 torsion angle of 0.7 (4)°.

The molecule is practically flat with a maximum deviation of 0.142 (5) Å (for atom C7) from the mean plane passing through the non-H atoms. The pyrazole ring (N3/N4/C15/C10/C9) is approximately planar with an r.m.s. deviation of 0.0026 Å. The C—C bond lengths of the pyrazole ring are 1.404 (6) and 1.428 (5) Å, the C—N bond lengths are 1.322 (5) and 1.359 (5) Å and the N—N bond length is 1.351 (4) Å, in good agreement with values reported previously for 7-methyl-1H-indazole [1.400 (4), 1.422 (4), 1.320 (4), 1.366 (3) and 1.356 (3) Å, respectively; Foces-Foces, 2005 ]

3. Supramolecular features

In the crystal, molecules are helically connected along the b-axis direction by N—H⋯N hydrogen bonds (Table 1 and Fig. 2). As a result, chiral crystals of achiral molecules are generated. The angles between the planes of neighbouring molecules in the hydrogen-bonded chains is 82.6 (2)°. Many examples of such achiral molecules forming chiral crystals have been reported, but the prediction of chiral crystallization is still not possible (Koshima & Matsuura, 1998 ; Matsuura & Koshima, 2005 ).

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C9–C14 and C9–C10/C15/N3–N4 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3n⋯N4ⁱ	0.88	2.06	2.851 (5)	149
C16ⁱⁱ—H16cⁱⁱ⋯Cg1	0.98	2.84	3.544	129
C16ⁱⁱ—H16cⁱⁱ⋯Cg3	0.98	2.93	3.832	154
Symmetry codes: (i) −x + 1, y + $[{1\over 2}]$ , −z; (ii) x, y − 1, z.

Figure 2
A view of the N—H⋯N hydrogen bonds (blue dashed lines) present in the crystal lattice of the title compound.

In addition, weak supramolecular interactions, such as the C16—H16c⋯Cg1 (2.844 Å) and C16—H16c⋯Cg3 (2.929 Å) C—H⋯π hydrogen bonds, are also found (Table 1 and Fig. 3).

Figure 3
A view of the various C—H⋯π interactions (blue dashed lines) present in the crystal lattice of the title compound.

4. Database survey

A similar compound, i.e. 7-methyl-1H-indazole (CCDC refcode 263698; Foces-Foces, 2005), has already been reported and shows a structure comparable with that of the title compound. However, surveys of the Cambridge Structural Database (CSD, Version 5.38; Groom et al., 2016 ) for the title compound revealed no hits. To our knowledge, this is the first crystal structure reported for indazole-type azo dyes.

5. Synthesis and crystallization

A mixture of 2,6-dimethylaniline (0.4847 g, 4.000 mmol), concentrated hydrochloric acid (37%, 1 ml) and water was heated and completely dissolved. The mixture was cooled in an ice bath and NaNO₂ (0.2967 g, 4.300 mmol) in 4.5 ml water was added. The reaction mixture was stirred at 273 K for 30 min and then salicylaldehyde (0.4885 g, 4.000 mmol) in 10 ml of a 10% NaOH aqueous solution was added dropwise and allowed to stir for an additional 1 h. The obtained orange precipitate was filtered off, washed with water and dried in a desiccator for several days (yield 0.2650 g, 26.06%). This crude orange compound was recrystallized by slow evaporation from acetone to give orange prismatic single crystals. IR (KBr, cm⁻¹): 746 (s), 1147 (s), 1162 (s), 1425 (m), 2923 (s), 3136 (br). ¹H NMR (300 MHz, DMSO): δ 2.36 (s, 6H), 2.56 (s, 3H), 7.18–7.23 (m, 5H), 8.02 (d, 1H)

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. All H atoms were located in difference Fourier maps. C-bound H atoms were constrained using a riding model [C—H = 0.95 Å and U_iso(H) = 1.2U_eq(C) for aromatic H atoms, and C—H = 0.98 Å and U_iso(H) = 1.5U_eq(C) for methyl H atoms]. N-bound H atoms were constrained using a riding model [N—H = 0.88 Å and U_iso(H) = 1.2U_eq(N)].

Table 2
Experimental details

Crystal data
Chemical formula	C₁₆H₁₆N₄
M_r	264.33
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	173
a, b, c (Å)	11.052 (8), 4.565 (4), 13.541 (10)
β (°)	97.997 (11)
V (Å³)	676.5 (9)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.12 × 0.09

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2001 )
T_min, T_max	0.323, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	3767, 2682, 2055
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.655

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.180, 1.01
No. of reflections	2682
No. of parameters	184
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.34
Absolute structure	Flack x determined using 636 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013
Absolute structure parameter	−10.0 (10)
Computer programs: APEX2 and SAINT (Bruker, 2014 ), SHELXT (Sheldrick, 2015a ), SHELXL2014 (Sheldrick, 2015b ), ORTEP-3 for Windows (Farrugia, 2012 ), Mercury (Macrae et al., 2006 ), SHELXTL (Sheldrick, 2008 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1865810

Crystal structure: contains datablock global. DOI: https://doi.org/10.1107/S2056989018012483/eb2011sup1.cif

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010).

(E)-3-[(2,6-Dimethylphenyl)diazenyl]-7-methyl-1H-indazole top

Crystal data top

C₁₆H₁₆N₄	F(000) = 280
M_r = 264.33	D_x = 1.297 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 11.052 (8) Å	Cell parameters from 1267 reflections
b = 4.565 (4) Å	θ = 2.6–26.0°
c = 13.541 (10) Å	µ = 0.08 mm⁻¹
β = 97.997 (11)°	T = 173 K
V = 676.5 (9) Å³	Prism, orange
Z = 2	0.30 × 0.12 × 0.09 mm

Data collection top

Bruker APEXII CCD diffractometer	2682 independent reflections
Radiation source: fine-focus sealed tube	2055 reflections with I > 2σ(I)
Detector resolution: 8.3333 pixels mm^-1	R_int = 0.053
φ and ω scans	θ_max = 27.7°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −11→14
T_min = 0.323, T_max = 0.746	k = −5→5
3767 measured reflections	l = −17→15

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.067	H-atom parameters constrained
wR(F²) = 0.180	w = 1/[σ²(F_o²) + (0.0993P)²] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
2682 reflections	Δρ_max = 0.28 e Å⁻³
184 parameters	Δρ_min = −0.34 e Å⁻³
1 restraint	Absolute structure: Flack x determined using 636 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −10.0 (10)

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
N3	0.4743 (3)	0.9544 (8)	0.0970 (2)	0.0333 (8)
H3n	0.4345	1.067	0.0507	0.04*
N1	0.7288 (3)	0.3286 (8)	0.2528 (2)	0.0334 (8)
N4	0.5704 (3)	0.7839 (8)	0.0832 (2)	0.0334 (8)
N2	0.7017 (3)	0.4534 (8)	0.1693 (2)	0.0342 (8)
C10	0.5295 (3)	0.7301 (9)	0.2424 (3)	0.0302 (9)
C15	0.6037 (3)	0.6474 (9)	0.1687 (3)	0.0298 (8)
C9	0.4468 (3)	0.9302 (9)	0.1914 (3)	0.0318 (9)
C1	0.8281 (3)	0.1267 (9)	0.2607 (3)	0.0327 (9)
C14	0.3515 (3)	1.0650 (10)	0.2343 (3)	0.0371 (10)
C11	0.5210 (3)	0.6599 (10)	0.3412 (3)	0.0374 (10)
H11	0.5759	0.5253	0.3774	0.045*
C6	0.8553 (3)	0.0120 (9)	0.3576 (3)	0.0359 (10)
C2	0.8945 (3)	0.0392 (10)	0.1838 (3)	0.0374 (10)
C5	0.9517 (4)	−0.1836 (10)	0.3778 (3)	0.0432 (10)
H5	0.9722	−0.2586	0.4434	0.052*
C13	0.3463 (4)	0.9899 (10)	0.3307 (3)	0.0423 (11)
H13	0.2839	1.073	0.3634	0.051*
C3	0.9897 (4)	−0.1594 (11)	0.2094 (4)	0.0450 (11)
H3	1.0367	−0.2205	0.1595	0.054*
C8	0.7839 (3)	0.0999 (11)	0.4390 (3)	0.0423 (11)
H8a	0.8096	−0.0192	0.4984	0.063*
H8b	0.6966	0.0693	0.4167	0.063*
H8c	0.7988	0.3073	0.455	0.063*
C4	1.0178 (4)	−0.2699 (11)	0.3043 (4)	0.0503 (12)
H4	1.0829	−0.406	0.3189	0.06*
C12	0.4300 (4)	0.7932 (11)	0.3843 (3)	0.0470 (12)
H12	0.423	0.7523	0.4521	0.056*
C7	0.8686 (4)	0.1420 (12)	0.0775 (3)	0.0467 (11)
H7a	0.8869	0.3516	0.0744	0.07*
H7b	0.7823	0.1085	0.0522	0.07*
H7c	0.9198	0.0329	0.0367	0.07*
C16	0.2633 (4)	1.2688 (12)	0.1738 (4)	0.0497 (12)
H16a	0.1983	1.3235	0.2127	0.075*
H16b	0.2275	1.1704	0.1123	0.075*
H16c	0.3067	1.4453	0.1571	0.075*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N3	0.0304 (16)	0.0403 (19)	0.0275 (16)	0.0049 (15)	−0.0023 (12)	0.0025 (15)
N1	0.0317 (16)	0.036 (2)	0.0316 (17)	−0.0040 (15)	0.0026 (12)	0.0015 (16)
N4	0.0327 (16)	0.0404 (19)	0.0264 (16)	−0.0015 (15)	0.0014 (11)	0.0010 (15)
N2	0.0321 (16)	0.041 (2)	0.0294 (17)	−0.0021 (15)	0.0036 (12)	−0.0001 (16)
C10	0.0258 (17)	0.033 (2)	0.0308 (19)	−0.0040 (15)	0.0022 (13)	−0.0006 (16)
C15	0.0321 (18)	0.033 (2)	0.0246 (18)	−0.0035 (17)	0.0039 (13)	−0.0007 (16)
C9	0.0298 (18)	0.033 (2)	0.032 (2)	−0.0044 (16)	0.0030 (14)	−0.0029 (18)
C1	0.0253 (18)	0.033 (2)	0.040 (2)	−0.0062 (17)	0.0044 (14)	−0.0061 (19)
C14	0.0299 (19)	0.036 (2)	0.046 (2)	−0.0031 (17)	0.0067 (16)	−0.0062 (19)
C11	0.038 (2)	0.044 (3)	0.030 (2)	−0.0034 (19)	0.0046 (15)	0.0007 (19)
C6	0.0288 (19)	0.038 (2)	0.040 (2)	−0.0060 (18)	0.0002 (15)	−0.0015 (19)
C2	0.033 (2)	0.039 (2)	0.041 (2)	−0.0055 (18)	0.0074 (16)	−0.0062 (19)
C5	0.034 (2)	0.045 (3)	0.049 (3)	0.002 (2)	−0.0040 (17)	−0.002 (2)
C13	0.037 (2)	0.045 (3)	0.047 (2)	0.002 (2)	0.0119 (18)	−0.010 (2)
C3	0.033 (2)	0.048 (3)	0.055 (3)	0.0017 (19)	0.0086 (18)	−0.010 (2)
C8	0.034 (2)	0.057 (3)	0.034 (2)	−0.002 (2)	−0.0004 (15)	0.002 (2)
C4	0.036 (2)	0.051 (3)	0.063 (3)	0.006 (2)	0.0011 (19)	−0.002 (2)
C12	0.054 (3)	0.056 (3)	0.034 (2)	−0.002 (2)	0.0164 (19)	−0.002 (2)
C7	0.043 (2)	0.059 (3)	0.040 (2)	0.002 (2)	0.0139 (17)	−0.005 (2)
C16	0.039 (2)	0.047 (3)	0.063 (3)	0.007 (2)	0.0066 (19)	0.002 (3)

Geometric parameters (Å, º) top

N3—N4	1.351 (4)	C2—C3	1.396 (6)
N3—C9	1.359 (5)	C2—C7	1.503 (6)
N3—H3n	0.88	C5—C4	1.371 (6)
N1—N2	1.265 (4)	C5—H5	0.95
N1—C1	1.426 (5)	C13—C12	1.415 (6)
N4—C15	1.322 (5)	C13—H13	0.95
N2—C15	1.399 (5)	C3—C4	1.375 (7)
C10—C11	1.391 (5)	C3—H3	0.95
C10—C9	1.404 (6)	C8—H8a	0.98
C10—C15	1.428 (5)	C8—H8b	0.98
C9—C14	1.412 (5)	C8—H8c	0.98
C1—C6	1.406 (6)	C4—H4	0.95
C1—C2	1.413 (5)	C12—H12	0.95
C14—C13	1.358 (6)	C7—H7a	0.98
C14—C16	1.505 (6)	C7—H7b	0.98
C11—C12	1.374 (6)	C7—H7c	0.98
C11—H11	0.95	C16—H16a	0.98
C6—C5	1.388 (5)	C16—H16b	0.98
C6—C8	1.496 (6)	C16—H16c	0.98

N4—N3—C9	111.5 (3)	C6—C5—H5	119.5
N4—N3—H3n	124.2	C14—C13—C12	122.8 (4)
C9—N3—H3n	124.2	C14—C13—H13	118.6
N2—N1—C1	116.2 (3)	C12—C13—H13	118.6
C15—N4—N3	106.2 (3)	C4—C3—C2	122.4 (4)
N1—N2—C15	112.1 (3)	C4—C3—H3	118.8
C11—C10—C9	119.8 (4)	C2—C3—H3	118.8
C11—C10—C15	137.1 (4)	C6—C8—H8a	109.5
C9—C10—C15	103.1 (3)	C6—C8—H8b	109.5
N4—C15—N2	115.1 (3)	H8a—C8—H8b	109.5
N4—C15—C10	111.8 (3)	C6—C8—H8c	109.5
N2—C15—C10	133.1 (4)	H8a—C8—H8c	109.5
N3—C9—C10	107.5 (3)	H8b—C8—H8c	109.5
N3—C9—C14	129.0 (4)	C5—C4—C3	119.9 (4)
C10—C9—C14	123.5 (4)	C5—C4—H4	120.0
C6—C1—C2	121.1 (4)	C3—C4—H4	120.0
C6—C1—N1	111.9 (3)	C11—C12—C13	121.8 (4)
C2—C1—N1	127.0 (4)	C11—C12—H12	119.1
C13—C14—C9	114.8 (4)	C13—C12—H12	119.1
C13—C14—C16	124.6 (4)	C2—C7—H7a	109.5
C9—C14—C16	120.6 (4)	C2—C7—H7b	109.5
C12—C11—C10	117.2 (4)	H7a—C7—H7b	109.5
C12—C11—H11	121.4	C2—C7—H7c	109.5
C10—C11—H11	121.4	H7a—C7—H7c	109.5
C5—C6—C1	118.8 (4)	H7b—C7—H7c	109.5
C5—C6—C8	119.8 (4)	C14—C16—H16a	109.5
C1—C6—C8	121.4 (4)	C14—C16—H16b	109.5
C3—C2—C1	116.8 (4)	H16a—C16—H16b	109.5
C3—C2—C7	118.5 (3)	C14—C16—H16c	109.5
C1—C2—C7	124.6 (4)	H16a—C16—H16c	109.5
C4—C5—C6	120.9 (4)	H16b—C16—H16c	109.5
C4—C5—H5	119.5

C9—N3—N4—C15	0.7 (4)	C10—C9—C14—C16	−177.7 (4)
C1—N1—N2—C15	−179.8 (3)	C9—C10—C11—C12	0.1 (6)
N3—N4—C15—N2	178.8 (3)	C15—C10—C11—C12	−178.5 (5)
N3—N4—C15—C10	−0.7 (4)	C2—C1—C6—C5	2.0 (6)
N1—N2—C15—N4	−179.6 (3)	N1—C1—C6—C5	−178.7 (3)
N1—N2—C15—C10	−0.2 (6)	C2—C1—C6—C8	−178.9 (4)
C11—C10—C15—N4	179.2 (4)	N1—C1—C6—C8	0.4 (5)
C9—C10—C15—N4	0.5 (4)	C6—C1—C2—C3	−1.6 (6)
C11—C10—C15—N2	−0.2 (8)	N1—C1—C2—C3	179.2 (3)
C9—C10—C15—N2	−178.9 (4)	C6—C1—C2—C7	177.6 (4)
N4—N3—C9—C10	−0.4 (4)	N1—C1—C2—C7	−1.6 (7)
N4—N3—C9—C14	−178.1 (4)	C1—C6—C5—C4	−1.6 (6)
C11—C10—C9—N3	−179.0 (4)	C8—C6—C5—C4	179.3 (4)
C15—C10—C9—N3	0.0 (4)	C9—C14—C13—C12	0.3 (6)
C11—C10—C9—C14	−1.2 (6)	C16—C14—C13—C12	178.9 (4)
C15—C10—C9—C14	177.8 (4)	C1—C2—C3—C4	0.8 (7)
N2—N1—C1—C6	176.8 (3)	C7—C2—C3—C4	−178.5 (4)
N2—N1—C1—C2	−3.9 (6)	C6—C5—C4—C3	0.8 (7)
N3—C9—C14—C13	178.3 (4)	C2—C3—C4—C5	−0.5 (7)
C10—C9—C14—C13	1.0 (6)	C10—C11—C12—C13	1.2 (6)
N3—C9—C14—C16	−0.3 (7)	C14—C13—C12—C11	−1.4 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3n···N4ⁱ	0.88	2.06	2.851 (5)	149
C16ⁱⁱ—H16cⁱⁱ···Cg1	0.98	2.84	3.544	129
C16ⁱⁱ—H16cⁱⁱ···Cg2	0.98	2.93	3.832	154

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

Hydrogen-bond geometry (Å, °). top

Cg1 and Cg2 are the centroids of the C9–C14 and C9–C10/C15/N3–N4 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3n···N4ⁱ	0.88	2.06	2.851 (5)	149
C16ⁱⁱ—H16cⁱⁱ···Cg1	0.98	2.84	3.544	129
C16ⁱⁱ—H16cⁱⁱ···Cg3	0.98	2.93	3.832	154

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

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Volume 74| Part 10| October 2018| Pages 1421-1423

https://doi.org/10.1107/S2056989018012483

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

Crystal structure of (E)-3-[(2,6-di­methyl­phen­yl)diazen­yl]-7-methyl-1H-indazole

1. Chemical context

2. Structural commentary

3. Supra­molecular features

4. Database survey

5. Synthesis and crystallization

6. Refinement

Supporting information

References

research communications

Crystal structure of (E)-3-[(2,6-dimethylphenyl)diazenyl]-7-methyl-1H-indazole

3. Supramolecular features