Syntheses, crystal structures and Hirshfeld surface analyses of (E)-1-[2,2-di­chloro-1-(2,3-di­meth­oxyphen­yl)ethen-1-yl]-2-phenyl­diazene and (E)-1-(4-chloro­phen­yl)-2-[2,2-di­chloro-1-(2,3-di­meth­oxy­phen­yl)ethen-1-yl]diazene

Shikhaliyev, N.Q.; Mammadova, N.; Atakishiyeva, G.T.; Huseynova, P.A.; Babayeva, G.V.; Mirzayeva, G.A.; Akkurt, M.; Bhattarai, A.

doi:10.1107/S2056989026000137

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ISSN: 2056-9890

Volume 82| Part 2| February 2026| Pages 156-162

https://doi.org/10.1107/S2056989026000137

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Syntheses, crystal structures and Hirshfeld surface analyses of (E)-1-[2,2-dichloro-1-(2,3-dimethoxyphenyl)ethen-1-yl]-2-phenyldiazene and (E)-1-(4-chlorophenyl)-2-[2,2-dichloro-1-(2,3-dimethoxyphenyl)ethen-1-yl]diazene

Namiq Q. Shikhaliyev,^a Naila Mammadova,^a Gulnar T. Atakishiyeva,^b Peri A. Huseynova,^c Gulnara V. Babayeva,^d Gulnaz A. Mirzayeva,^e Mehmet Akkurt ^f and Ajaya Bhattarai ^g ^*

^aDepartment of Chemical Engineering, Baku Engineering University, Khirdalan City, 120 AZ0101 Hasan Aliyev Street, Baku, Azerbaijan, ^bOrganic Chemistry Department, Baku State University, Z. Khalilov str. 23, AZ 1148 Baku, Azerbaijan, ^cChemistry Department, Nakhchivan State University, University Campus, AZ7012, Nakhcivan, Azerbaijan, ^dDepartment of Analytical and Organic Chemistry, Azerbaijan State Pedagogical University, 68 Uzeyir Hajibeyli str., Baku AZ1000, Azerbaijan, ^eDepartment of Chemical Technology, Recycling and Ecology, Azerbaijan Technical University, Baku, Azerbaijan, H. Javid ave 25, AZ 1073 Baku, Azerbaijan, ^fDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Türkiye, and ^gDepartment of Chemistry, M.M.A.M.C (Tribhuvan University) Biratnagar, Nepal
^*Correspondence e-mail: [email protected]

Edited by X. Hao, Institute of Chemistry, Chinese Academy of Sciences (Received 5 January 2026; accepted 7 January 2026; online 13 January 2026)

The crystal structures and Hirshfeld surface analyses of two similar azo compounds are reported. (E)-1-[2,2-dichloro-1-(2,3-dimethoxyphenyl)ethen-1-yl]-2-phenyldiazene, C₁₆H₁₄Cl₂N₂O₂, (I), crystallizes in space group P2₁/c with Z = 4, and (E)-1-(4-chlorophenyl)-2-[2,2-dichloro-1-(2,3-dimethoxyphenyl)ethen-1-yl]diazene, C₁₆H₁₃Cl₃N₂O₂, (II), in the space group P1 with Z = 4. In the crystal structure of (I), the molecules form layers parallel to the (010) plane through C—H⋯π and C—Cl⋯π interactions and van der Waals interactions between these layers consolidate the packing. There are two symmetry-independent molecules in the asymmetric unit of (II). In the crystal, molecules are connected by C—H⋯O and C—H⋯Cl hydrogen bonds, forming a three-dimensional network. C—Cl⋯π interactions also contribute to the packing. The intermolecular contacts in the crystals (I) and (II) were analysed using Hirshfeld surface analysis and two-dimensional fingerprint plots.

Keywords: crystal structure; C—H⋯π interactions; C—Cl⋯π interactions; van der Waals interactions; Hirshfeld surface analysis.

CCDC references: 2521000; 2520999

1. Chemical context

Azo dyes continue to attract considerable attention due to their wide applications in the textile (O'Neill et al., 2000 ; Garg et al., 2017 ), optical (Al-Mudhaffer et al., 2016 ; Mohr & Wolfbeis, 1994 ), and biological fields (Khan et al., 2021 ; Singh & Singh, 2017 ). The presence of functional groups in the obtained compounds provides broad opportunities for further chemical transformations and structural modifications. In this paper, we report the synthesis of two new dichlorodiazadienes, namely (E)-1-[2,2-dichloro-1-(2,3-dimethoxyphenyl)ethen-1-yl]-2-phenyldiazene, C₁₆H₁₄Cl₂N₂O₂, (I), and (E)-1-(4-chlorophenyl)-2-[2,2-dichloro-1-(2,3-dimethoxyphenyl)ethen-1-yl]diazene, C₁₆H₁₃Cl₃N₂O₂, (II). These compounds were synthesized in two steps starting from 2,3-dimethoxybenzaldehyde and phenylhydrazine and its chloro-substituted derivative. In the first step, the corresponding Schiff bases were obtained by condensation in ethanol under reflux in the presence of acetic acid. In the second step, the resulting hydrazones were converted into the target azo dyes by reaction with carbon tetrachloride in DMSO at room temperature in the presence of a CuCl₂ catalyst and tetramethylethylenediamine (TMEDA) (Fig. 1).

Figure 1
Reaction scheme for compounds (I) and (II).

The formation of a dichloroethenyl fragment and an azo (–N=N–) chromophore within the same molecular system significantly enhances the functional diversity of the synthesized compounds. Such structural features not only affect their electronic and optical properties, but also enable their participation in various intermolecular interactions in the solid state. Therefore, in addition to the synthesis, detailed single-crystal X-ray diffraction and Hirshfeld surface analyses were performed to investigate the molecular and supramolecular structures of compounds (I) and (II).

2. Structural commentary

The central molecular fragment of (I), C1/C2/N1/N2/C3/C11/Cl1/Cl2, is almost planar (Fig. 2), with a root-mean-square (r.m.s.) deviation of fitted atoms from the least-squares plane of 0.0304 Å. This plane forms dihedral angles of 80.8 (1) and 26.7 (1) °, respectively, with the planes of the C3–C8 and C11–C16 benzene rings. The conformation of molecule (I) may be consolidated by a short C—H⋯O contact (Table 1, Fig. 2), forming an S(6) motif.

Table 1
Hydrogen-bond geometry (Å, °) for (I)

Cg and Cg2 are the centroids of the C3–C8 and C11–C16 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9B⋯O2	0.98	2.35	2.955 (2)	119
C8—H8⋯Cg2ⁱ	0.95	2.52	3.4665 (16)	174
C10—H10A⋯Cg1ⁱⁱ	0.98	2.77	3.6231 (18)	146
Symmetry codes: (i) ; (ii) .

Figure 2
The molecular structure of (I), showing the atom labelling and displacement ellipsoids drawn at the 50% probability level. The short contact is indicated by a dashed line.

There are two symmetry-independent molecules, A (containing N1) and B (containing N3), in the asymmetric unit of (II) (Fig. 3). An overlay fit of inverted molecule B on molecule A is shown in Fig. 4, the weighted r.m.s. fit of the 17 non-H atoms being 0.200 Å and showing the differences to be in the chlorophenyl groups C11–C16 and C27–C32. The central molecular fragment of molecule A, C1/C2/N2/N1/C3/C11/Cl1/Cl2, is also close to planar with an r.m.s. deviation of fitted atoms of 0.0226 Å (Fig. 3) and makes dihedral angles of 72.9 (1) and 6.6 (1)°, respectively, with the planes of the C3–C8 and C11–C16 benzene rings. The central molecular fragment of molecule B, C17/C18/N3/N4/C19/C27/Cl4/Cl5, is likewise almost planar with an r.m.s. deviation of fitted atoms of 0.0472 Å (Fig. 3) and makes dihedral angles of 69.1 (1) and 22.7 (1)°, respectively, with the planes of the (C19–C24) and (C27–C32) benzene rings. The conformation of molecule A features an intramolecular C—H⋯O hydrogen bond forming an S(6) motif, while the conformation of molecule B features intramolecular C—H⋯O and C—H⋯N hydrogen bonds (Table 2), which form S(6) and S(8) motifs, respectively.

Table 2
Hydrogen-bond geometry (Å, °) for (II)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9C⋯O2	0.98	2.32	2.9059 (12)	117
C10—H10C⋯O3ⁱ	0.98	2.65	3.3241 (13)	126
C12—H12⋯O1ⁱⁱ	0.95	2.66	3.2919 (11)	125
C25—H25B⋯O4	0.98	2.33	2.9226 (12)	118
C25—H25C⋯N4	0.98	2.58	3.2210 (13)	124
C31—H31⋯Cl2ⁱⁱⁱ	0.95	2.87	3.7991 (10)	166
Symmetry codes: (i) ; (ii) ; (iii) .

Figure 3
The molecular structure of (II), showing the atom labelling and displacement ellipsoids drawn at the 50% probability level. Hydrogen bonds are indicated by dashed lines.

Figure 4
A least-squares overlay of the two independent molecules A and B of (II)

[inverted molecule B (red) on molecule A (black)].

3. Supramolecular features and Hirshfeld surface analyses

In the crystal structure of (I), the molecules form layers parallel to the (020) plane through C—H⋯π and C—Cl⋯π interactions [C2—Cl2⋯Cg2^a: C2—Cl2 = 1.7131 (15) Å, Cl2⋯Cg2^a = 3.9882 (7) Å, C2⋯Cg2^a = 4.2031 (16) Å, C2—Cl2⋯Cg2^a = 85.07 (5)°, Symmetry code: (a) x, y, 1 + z; where Cg2 is the centroid of the (C11–C16) benzene ring] (Table 1, Figs. 5 and 6). van der Waals interactions between these layers consolidate the packing.

Figure 5
View of the C—H⋯π and C—Cl⋯π interactions of (I) along the a axis. H atoms not involved in hydrogen bonding were removed for clarity.

Figure 6
View of the C—H⋯π and C—Cl⋯π interactions of (I) along the c axis. H atoms not involved in hydrogen bonding were removed for clarity.

In the crystal of (II), the molecules are connected by C—H⋯O and C—H⋯Cl hydrogen bonds, forming a three-dimensional network (Table 2, Figs. 7 and 8). Additionally, C—Cl⋯π interactions [C2—Cl2⋯Cg2^b: C2—Cl2 = 1.7149 (9) Å, Cl2⋯Cg2^b = 3.4334 (7) Å, C2⋯Cg2^b = 3.7761 (11) Å, C2—Cl2⋯Cg2^b = 87.72 (3), and C18—Cl5⋯Cg4^c: C18—Cl5 = 1.7159 (9) Å, Cl5⋯Cg4^c = 3.8775 (7) Å, C18⋯Cg4^c = 4.1527 (13) Å, C18—Cl5⋯Cg4^c = 86.84 (4)°, Symmetry codes: (b) 1 − x, −y, 1 − z; (c) 2 − x, 1 − y, −z; where Cg2 and Cg4 are the centroids of the chlorophenyl rings (C11–C16 and C27–C32) of molecules A and B, respectively] also contribute to the packing.

Figure 7
View of the C—H⋯O and C—H—Cl interactions (II) along the b axis. H atoms not involved in hydrogen bonding were removed for clarity.

Figure 8
View of the C—H⋯O and C—H—Cl interactions (II) along the c axis. H atoms not involved in hydrogen bonding were removed for clarity.

Crystal Explorer 17.5 (Spackman et al., 2021 ) was used to generate Hirshfeld surfaces in the crystal structures of (I) and (II). The d_norm mappings for (I) and molecules A and B of (II) were performed in the ranges −0.12 to 1.21 a.u., −0.10 to 1.35 a.u. and −0.10 to 1.66 a.u., respectively. The C⋯H/H⋯C, Cl⋯H/H⋯Cl and O⋯H/H⋯O interactions are indicated by red areas on the Hirshfeld surfaces (Fig. 9a for (I) and Fig. 9c,d for molecules A and B of (II). The two-dimensional fingerprint plots are shown in Fig. 10. The dominant interactions in the crystal packing of the title compounds are H⋯H [(I): 35.9%, (II) A: 29.6% and (II) B: 28.2%], C⋯H/H⋯C [(I): 21.1%, (II) A: 13.6% and (II) B: 12.0%], Cl⋯H/H⋯Cl [(I): 20.2%, (II) A: 29.1% and (II) B: 31.3%], O⋯H/H⋯O [(I): 7.6%, (II) A: 7.5% and (II) B: 7.1%]. The presence of different functional groups in the compounds leads to some differences in the remaining weak interactions.

Figure 9
The Hirshfeld surfaces of (a) (I), (b) (II) molecule A and (c) (II) molecule B plotted over d_norm.

Figure 10
The full two-dimensional fingerprint plots for (I) and (II), showing (a) all interactions, and delineated into (b) H⋯H, (c) C⋯H/H⋯C for (I) [Cl⋯H/H⋯Cl for molecules A and B of (II)] and (d) Cl⋯H/H⋯Cl for (I) (C⋯H/H⋯C for molecules A and B of (II)] interactions. The d_i and d_e values are the closest internal and external distances (in Å) from given points on the Hirshfeld surface.

4. Database survey

A search of the Cambridge Structural Database (CSD, Version 6.00, update of April 2025; Groom et al., 2016 ) for the (E)-1-(2,2-dichloro-1-phenylethen-1-yl)-2-phenyldiazene moiety resulted in 39 hits. Eight compounds are most similar to the title compound, viz. those with CSD refcodes POCXIS (Shikhaliyev et al., 2024 ), NIKXEO (Maharramov et al., 2023 ), TAZDIL (Atioğlu et al., 2022 ), HEHKEO (Akkurt et al., 2022 ), PAXDOL (Çelikesir et al., 2022 ), CANVUM (Shikhaliyev et al., 2021 ), GUPHIL (Özkaraca et al., 2020 ), HODQAV (Shikhaliyev et al., 2019 ).

In the crystal of POCXIS, molecules are linked by C—H⋯N hydrogen bonds, forming chains with C(6) motifs parallel to the b axis. Short intermolecular Cl⋯O contacts of 2.8421 (16) Å and weak van der Waals interactions between these chains consolidate the crystal structure. In the crystal structure of NIKXEO, molecules are linked by C—H⋯π and C—Cl⋯π interactions, forming layers parallel to ( $[\overline{1}]$ 01). The cohesion of the packing is ensured by van der Waals forces between these layers. The molecules in TAZDIL are joined into layers parallel to (011) by C—H⋯O and C—H⋯F hydrogen bonds. C—Br⋯π and C—F⋯π contacts, as well as π–π stacking interactions consolidate the crystal packing. C—H⋯Br interactions connect the molecules in the crystal of the polymorph-1 of HEHKEO, resulting in zigzag C(8) chains parallel to [100]. These chains are connected by C—Br⋯π interactions into layers parallel to (001). van der Waals interactions between the layers contribute to the crystal cohesion. The molecules in the crystal of PAXDOL are connected into chains running parallel to [001] by C—H⋯O hydrogen bonds. C—F⋯π contacts and π–π stacking interactions help to consolidate the crystal packing, and short Br⋯O [2.9828 (13) Å] distances are also observed. In CANVUM, the molecules are linked by C—H⋯N interactions along [100], forming a C(6) chain. The molecules are further connected by C—Cl⋯π interactions and face-to-face π–π stacking interactions, resulting in ribbons along [100]. In GUPHIL, molecules are associated into inversion dimers via short Cl⋯Cl contacts [3.3763 (9) Å]. In HODQAV, molecules are stacked in columns along [100] via weak C—H⋯Cl hydrogen bonds and face-to-face π–π stacking interactions. The crystal packing is further consolidated by short Cl⋯Cl contacts.

5. Synthesis and crystallization

Compounds (I) and (II) were synthesized according to a literature protocol (Shikhaliyev et al., 2018 ). For (I), a 20 ml screw-neck vial was charged with dimethylsulfoxide (DMSO) (10 ml), (E)-1-(4-chlorophenyl)-2-(2,3-dimethoxybenzylidene)hydrazine (290 mg, 1 mmol), tetramethylethylenediamine (TMEDA) (295 mg, 2.5 mmol), CuCl (2 mg, 0.02 mmol) and CCl₄ (1 mmol). After 2–3 h (until TLC analysis showed complete consumption of the corresponding Schiff base), the reaction mixture was poured into a 0.01 M solution of HCl (100 ml, pH = 2–3), and extracted with dichloromethane (3 × 20 ml). The combined organic phase was washed with water (3 × 50 ml), brine (30 ml), dried over anhydrous Na₂SO₄ and concentrated in vacuum using a rotary evaporator. The residue was purified by column chromatography on silica gel using appropriate mixtures of hexane and dichloromethane (v/v: 5/1–3/1–1/1). A red solid was obtained (yield 65%); m.p. 365 K. ¹H NMR (300 MHz, chloroform-d) δ 7.71–7.69 (m, 2H, arom), 7.49–7.45 (m, 2H, arom), 7.30–7.25 (m, 1H, arom), 7.19–7.11 (m, 3H, arom), 3.71 (s, 3H, –OCH₃), 3.84 (s, 3H, OCH₃). ¹³C NMR (75 MHz, CDCl₃) 152.4, 151.7, 149.5, 133.8, 130.7, 129.2, 128.3, 128.1, 127.7, 124.9, 121.7, 117.6, 60.6, 56.0.

For (II), the procedure was the same as that for (I) using methyl (E)-1-(4-chlorophenyl)-2-(2,3-dimethoxybenzylidene)hydrazine (290 mg, 1 mmol). A red solid was obtained (yield 78%); m.p. 399 K. ¹H NMR (300 MHz, chloroform-d) δ 7.67–7.60 (m, 1H, arom), 7.52–7.45 (m, 1H, arom), 7.18–7.05 (m, 1H, arom), 3.75 (s, 1H, –OCH₃), 3.98 (s, 1H, –OCH₃). ¹³C NMR (75 MHz, CDCl₃) 151.8, 151.0, 149.7, 136.7, 133.3, 129.1, 128.4, 128.0, 127.6, 124.6, 117.7, 114.6, 67.6, 54.6.

In each case, the obtained compound was dissolved in dichloromethane and then left at room temperature for slow evaporation; red single crystals suitable for X-ray diffraction analysis started to form after ca 2 d.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. H atoms were positioned geometrically and refined using a riding model [C—H = 0.95–0.98 Å and U_iso(H) = 1.2 or 1.5 U_eq(C)].

Table 3
Experimental details

	(I)	(II)
Crystal data
Chemical formula	C₁₆H₁₄Cl₂N₂O₂	C₁₆H₁₃Cl₃N₂O₂
M_r	337.19	371.63
Crystal system, space group	Monoclinic, P2₁/c	Triclinic, P $[\overline{1}]$
Temperature (K)	100	100
a, b, c (Å)	7.30389 (4), 30.68147 (13), 7.42658 (4)	8.2181 (11), 13.3651 (17), 16.687 (2)
α, β, γ (°)	90, 109.7560 (6), 90	108.139 (3), 94.732 (3), 106.396 (3)
V (Å³)	1566.30 (2)	1641.5 (4)
Z	4	4
Radiation type	Cu Kα	Mo Kα
μ (mm⁻¹)	3.80	0.57
Crystal size (mm)	0.13 × 0.11 × 0.06	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Rigaku XtaLAB Synergy-S, HyPix-6000HE area-detector	Bruker D8 QUEST PHOTON-III area detector
Absorption correction	Gaussian (CrysAlis PRO; Rigaku OD, 2025 )	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.641, 0.796	0.656, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	81705, 3424, 3376	39419, 11888, 10714
R_int	0.046	0.023
(sin θ/λ)_max (Å⁻¹)	0.639	0.758

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.082, 1.06	0.027, 0.074, 1.05
No. of reflections	3424	11888
No. of parameters	201	419
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.36	0.48, −0.36
Computer programs: CrysAlis PRO (Rigaku OD, 2021 ), APEX3 and SAINT (Bruker, 2018 ), SHELXT2014/5 (Sheldrick, 2015a ), SHELXL2018/3 (Sheldrick, 2015b ), ORTEP-3 for Windows (Farrugia, 2012 ) and PLATON (Spek, 2020 ).

Supporting information

CCDC references: 2521000; 2520999

Crystal structure: contains datablocks I, II. DOI: https://doi.org/10.1107/S2056989026000137/nx2031sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989026000137/nx2031Isup2.hkl

Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S2056989026000137/nx2031IIsup3.hkl

checkCIF report

Computing details top

(E)-1-[2,2-Dichloro-1-(2,3-dimethoxyphenyl)ethen-1-yl]-2-phenyldiazene (I) top

Crystal data top

C₁₆H₁₄Cl₂N₂O₂	F(000) = 696
M_r = 337.19	D_x = 1.430 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54184 Å
a = 7.30389 (4) Å	Cell parameters from 60750 reflections
b = 30.68147 (13) Å	θ = 2.9–79.6°
c = 7.42658 (4) Å	µ = 3.80 mm⁻¹
β = 109.7560 (6)°	T = 100 K
V = 1566.30 (2) Å³	Prism, brown
Z = 4	0.13 × 0.11 × 0.06 mm

Data collection top

Rigaku XtaLAB Synergy-S, HyPix-6000HE area-detector diffractometer	3376 reflections with I > 2σ(I)
Radiation source: micro-focus sealed X-ray tube	R_int = 0.046
φ and ω scans	θ_max = 80.0°, θ_min = 2.9°
Absorption correction: gaussian (CrysAlisPro; Rigaku OD, 2025)	h = −9→9
T_min = 0.641, T_max = 0.796	k = −39→39
81705 measured reflections	l = −9→9
3424 independent reflections

Refinement top

Refinement on F²	Primary atom site location: difference Fourier map
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.082	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0377P)² + 1.1051P] where P = (F_o² + 2F_c²)/3
3424 reflections	(Δ/σ)_max = 0.001
201 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

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
Cl1	0.29682 (5)	0.65828 (2)	0.93930 (5)	0.02571 (10)
Cl2	0.52050 (5)	0.72971 (2)	0.87184 (5)	0.02478 (10)
O1	0.73197 (15)	0.57980 (3)	0.88689 (15)	0.0228 (2)
O2	0.60438 (16)	0.49625 (3)	0.82871 (15)	0.0249 (2)
N1	0.63222 (17)	0.66977 (4)	0.62019 (17)	0.0194 (2)
N2	0.66515 (17)	0.64600 (4)	0.49630 (17)	0.0193 (2)
C1	0.5041 (2)	0.65062 (4)	0.7039 (2)	0.0186 (3)
C2	0.4487 (2)	0.67660 (5)	0.8224 (2)	0.0205 (3)
C3	0.4334 (2)	0.60489 (4)	0.6629 (2)	0.0183 (3)
C4	0.5525 (2)	0.57056 (4)	0.75418 (19)	0.0185 (3)
C5	0.4827 (2)	0.52744 (5)	0.7230 (2)	0.0201 (3)
C6	0.2983 (2)	0.51953 (5)	0.5918 (2)	0.0232 (3)
H6	0.251670	0.490476	0.566572	0.028*
C7	0.1820 (2)	0.55417 (5)	0.4975 (2)	0.0255 (3)
H7	0.056650	0.548542	0.407235	0.031*
C8	0.2470 (2)	0.59666 (5)	0.5339 (2)	0.0233 (3)
H8	0.165342	0.620149	0.471536	0.028*
C9	0.8957 (2)	0.56394 (6)	0.8398 (3)	0.0316 (4)
H9A	0.895488	0.577293	0.719845	0.047*
H9B	0.886635	0.532197	0.824871	0.047*
H9C	1.016507	0.571543	0.942622	0.047*
C10	0.5289 (3)	0.45272 (5)	0.8119 (2)	0.0284 (3)
H10A	0.502301	0.442238	0.680886	0.043*
H10B	0.408232	0.452573	0.842048	0.043*
H10C	0.624663	0.433599	0.901379	0.043*
C11	0.7989 (2)	0.66527 (4)	0.4167 (2)	0.0184 (3)
C12	0.7998 (2)	0.64778 (5)	0.2436 (2)	0.0202 (3)
H12	0.713531	0.624722	0.184687	0.024*
C13	0.9273 (2)	0.66424 (5)	0.1579 (2)	0.0222 (3)
H13	0.925250	0.653168	0.037768	0.027*
C14	1.0577 (2)	0.69685 (5)	0.2478 (2)	0.0226 (3)
H14	1.146914	0.707599	0.190471	0.027*
C15	1.0584 (2)	0.71388 (5)	0.4217 (2)	0.0230 (3)
H15	1.148738	0.736065	0.482808	0.028*
C16	0.9280 (2)	0.69868 (4)	0.5064 (2)	0.0206 (3)
H16	0.926334	0.710772	0.623627	0.025*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.02833 (18)	0.02687 (18)	0.02930 (19)	−0.00008 (13)	0.01938 (15)	−0.00127 (13)
Cl2	0.03005 (19)	0.01812 (17)	0.02945 (19)	−0.00041 (12)	0.01436 (15)	−0.00447 (12)
O1	0.0207 (5)	0.0220 (5)	0.0233 (5)	−0.0005 (4)	0.0046 (4)	−0.0033 (4)
O2	0.0309 (5)	0.0166 (5)	0.0272 (5)	−0.0004 (4)	0.0098 (4)	0.0016 (4)
N1	0.0206 (5)	0.0185 (5)	0.0218 (6)	0.0010 (4)	0.0105 (5)	0.0007 (4)
N2	0.0191 (5)	0.0197 (5)	0.0206 (6)	−0.0003 (4)	0.0088 (5)	−0.0007 (4)
C1	0.0184 (6)	0.0182 (6)	0.0203 (7)	0.0006 (5)	0.0079 (5)	0.0007 (5)
C2	0.0211 (6)	0.0202 (6)	0.0225 (7)	0.0005 (5)	0.0103 (5)	0.0006 (5)
C3	0.0199 (6)	0.0191 (6)	0.0195 (6)	−0.0015 (5)	0.0114 (5)	−0.0014 (5)
C4	0.0201 (6)	0.0203 (6)	0.0175 (6)	−0.0019 (5)	0.0095 (5)	−0.0029 (5)
C5	0.0248 (7)	0.0186 (6)	0.0208 (7)	−0.0003 (5)	0.0128 (6)	−0.0005 (5)
C6	0.0253 (7)	0.0211 (7)	0.0271 (7)	−0.0065 (5)	0.0138 (6)	−0.0044 (6)
C7	0.0194 (7)	0.0290 (8)	0.0280 (7)	−0.0046 (6)	0.0079 (6)	−0.0040 (6)
C8	0.0192 (6)	0.0240 (7)	0.0278 (7)	0.0014 (5)	0.0093 (6)	0.0005 (6)
C9	0.0206 (7)	0.0295 (8)	0.0432 (10)	0.0007 (6)	0.0090 (7)	−0.0034 (7)
C10	0.0393 (9)	0.0158 (7)	0.0332 (8)	−0.0017 (6)	0.0163 (7)	0.0016 (6)
C11	0.0194 (6)	0.0172 (6)	0.0204 (6)	0.0017 (5)	0.0091 (5)	0.0018 (5)
C12	0.0208 (6)	0.0208 (6)	0.0185 (6)	−0.0012 (5)	0.0061 (5)	−0.0015 (5)
C13	0.0251 (7)	0.0252 (7)	0.0178 (7)	0.0006 (6)	0.0093 (6)	0.0000 (5)
C14	0.0248 (7)	0.0217 (7)	0.0258 (7)	0.0000 (5)	0.0144 (6)	0.0035 (6)
C15	0.0258 (7)	0.0181 (6)	0.0277 (7)	−0.0033 (5)	0.0124 (6)	−0.0018 (6)
C16	0.0239 (7)	0.0188 (6)	0.0214 (7)	−0.0008 (5)	0.0107 (6)	−0.0029 (5)

Geometric parameters (Å, º) top

Cl1—C2	1.7182 (14)	C8—H8	0.9500
Cl2—C2	1.7131 (15)	C9—H9A	0.9800
O1—C4	1.3772 (17)	C9—H9B	0.9800
O1—C9	1.4395 (19)	C9—H9C	0.9800
O2—C5	1.3604 (18)	C10—H10A	0.9800
O2—C10	1.4341 (17)	C10—H10B	0.9800
N1—N2	1.2593 (17)	C10—H10C	0.9800
N1—C1	1.4141 (18)	C11—C12	1.3950 (19)
N2—C11	1.4296 (18)	C11—C16	1.3993 (19)
C1—C2	1.347 (2)	C12—C13	1.389 (2)
C1—C3	1.4905 (19)	C12—H12	0.9500
C3—C4	1.388 (2)	C13—C14	1.387 (2)
C3—C8	1.398 (2)	C13—H13	0.9500
C4—C5	1.4086 (19)	C14—C15	1.391 (2)
C5—C6	1.391 (2)	C14—H14	0.9500
C6—C7	1.393 (2)	C15—C16	1.388 (2)
C6—H6	0.9500	C15—H15	0.9500
C7—C8	1.382 (2)	C16—H16	0.9500
C7—H7	0.9500

C4—O1—C9	115.13 (11)	O1—C9—H9B	109.5
C5—O2—C10	116.62 (12)	H9A—C9—H9B	109.5
N2—N1—C1	113.49 (12)	O1—C9—H9C	109.5
N1—N2—C11	112.86 (11)	H9A—C9—H9C	109.5
C2—C1—N1	115.51 (12)	H9B—C9—H9C	109.5
C2—C1—C3	122.04 (13)	O2—C10—H10A	109.5
N1—C1—C3	122.44 (12)	O2—C10—H10B	109.5
C1—C2—Cl2	124.42 (11)	H10A—C10—H10B	109.5
C1—C2—Cl1	121.64 (11)	O2—C10—H10C	109.5
Cl2—C2—Cl1	113.94 (8)	H10A—C10—H10C	109.5
C4—C3—C8	120.14 (13)	H10B—C10—H10C	109.5
C4—C3—C1	119.85 (12)	C12—C11—C16	120.56 (13)
C8—C3—C1	120.01 (13)	C12—C11—N2	115.99 (12)
O1—C4—C3	118.77 (12)	C16—C11—N2	123.41 (12)
O1—C4—C5	120.99 (13)	C13—C12—C11	119.68 (13)
C3—C4—C5	120.01 (13)	C13—C12—H12	120.2
O2—C5—C6	124.78 (13)	C11—C12—H12	120.2
O2—C5—C4	115.87 (13)	C14—C13—C12	119.95 (13)
C6—C5—C4	119.34 (13)	C14—C13—H13	120.0
C5—C6—C7	120.04 (13)	C12—C13—H13	120.0
C5—C6—H6	120.0	C13—C14—C15	120.28 (13)
C7—C6—H6	120.0	C13—C14—H14	119.9
C8—C7—C6	120.71 (14)	C15—C14—H14	119.9
C8—C7—H7	119.6	C16—C15—C14	120.46 (13)
C6—C7—H7	119.6	C16—C15—H15	119.8
C7—C8—C3	119.66 (14)	C14—C15—H15	119.8
C7—C8—H8	120.2	C15—C16—C11	119.04 (13)
C3—C8—H8	120.2	C15—C16—H16	120.5
O1—C9—H9A	109.5	C11—C16—H16	120.5

C1—N1—N2—C11	−178.40 (11)	C3—C4—C5—O2	−175.49 (12)
N2—N1—C1—C2	−173.35 (13)	O1—C4—C5—C6	178.10 (12)
N2—N1—C1—C3	6.15 (19)	C3—C4—C5—C6	3.7 (2)
N1—C1—C2—Cl2	0.89 (19)	O2—C5—C6—C7	176.99 (13)
C3—C1—C2—Cl2	−178.62 (11)	C4—C5—C6—C7	−2.1 (2)
N1—C1—C2—Cl1	−178.88 (10)	C5—C6—C7—C8	−0.6 (2)
C3—C1—C2—Cl1	1.6 (2)	C6—C7—C8—C3	1.7 (2)
C2—C1—C3—C4	−101.19 (16)	C4—C3—C8—C7	−0.1 (2)
N1—C1—C3—C4	79.34 (17)	C1—C3—C8—C7	−179.60 (13)
C2—C1—C3—C8	78.30 (18)	N1—N2—C11—C12	−161.90 (12)
N1—C1—C3—C8	−101.17 (16)	N1—N2—C11—C16	20.25 (19)
C9—O1—C4—C3	−117.64 (14)	C16—C11—C12—C13	−1.2 (2)
C9—O1—C4—C5	67.90 (17)	N2—C11—C12—C13	−179.13 (13)
C8—C3—C4—O1	−177.11 (12)	C11—C12—C13—C14	2.3 (2)
C1—C3—C4—O1	2.38 (19)	C12—C13—C14—C15	−1.5 (2)
C8—C3—C4—C5	−2.6 (2)	C13—C14—C15—C16	−0.4 (2)
C1—C3—C4—C5	176.89 (12)	C14—C15—C16—C11	1.5 (2)
C10—O2—C5—C6	−4.7 (2)	C12—C11—C16—C15	−0.7 (2)
C10—O2—C5—C4	174.42 (12)	N2—C11—C16—C15	177.09 (13)
O1—C4—C5—O2	−1.09 (19)

Hydrogen-bond geometry (Å, º) top

Cg and Cg2 are the centroids of the C3–C8 and C11–C16 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9B···O2	0.98	2.35	2.955 (2)	119
C8—H8···Cg2ⁱ	0.95	2.52	3.4665 (16)	174
C10—H10A···Cg1ⁱⁱ	0.98	2.77	3.6231 (18)	146

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

(E)-1-(4-Chlorophenyl)-2-[2,2-dichloro-1-(2,3-dimethoxyphenyl)ethen-1-yl]diazene (II) top

Crystal data top

C₁₆H₁₃Cl₃N₂O₂	Z = 4
M_r = 371.63	F(000) = 760
Triclinic, P1	D_x = 1.504 Mg m⁻³
a = 8.2181 (11) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.3651 (17) Å	Cell parameters from 9797 reflections
c = 16.687 (2) Å	θ = 2.5–32.6°
α = 108.139 (3)°	µ = 0.57 mm⁻¹
β = 94.732 (3)°	T = 100 K
γ = 106.396 (3)°	Prism, red
V = 1641.5 (4) Å³	0.30 × 0.20 × 0.20 mm

Data collection top

Bruker D8 QUEST PHOTON-III area detector diffractometer	10714 reflections with I > 2σ(I)
Radiation source: fine-focus sealed X-ray tube	R_int = 0.023
φ and ω scans	θ_max = 32.6°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −12→12
T_min = 0.656, T_max = 0.746	k = −20→20
39419 measured reflections	l = −25→25
11888 independent reflections

Refinement top

Refinement on F²	Primary atom site location: difference Fourier map
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.074	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0326P)² + 0.5553P] where P = (F_o² + 2F_c²)/3
11888 reflections	(Δ/σ)_max = 0.002
419 parameters	Δρ_max = 0.48 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Special details top

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

	x	y	z	U_iso*/U_eq
Cl1	0.52462 (3)	0.39382 (2)	0.61838 (2)	0.01884 (4)
Cl2	0.60551 (3)	0.22480 (2)	0.67158 (2)	0.01681 (4)
Cl3	0.93613 (3)	−0.29765 (2)	0.35426 (2)	0.02135 (5)
O1	0.37126 (8)	0.14223 (5)	0.37547 (4)	0.01618 (11)
O2	0.35903 (9)	0.22142 (7)	0.24322 (4)	0.02241 (14)
N1	0.68510 (9)	0.14189 (6)	0.50182 (5)	0.01367 (12)
N2	0.73277 (9)	0.10900 (6)	0.43084 (5)	0.01397 (12)
C1	0.63666 (10)	0.23844 (7)	0.51515 (5)	0.01289 (13)
C2	0.59557 (10)	0.28070 (7)	0.59243 (5)	0.01407 (13)
C3	0.62956 (11)	0.28996 (7)	0.44848 (5)	0.01406 (13)
C4	0.49846 (11)	0.23529 (7)	0.37639 (5)	0.01431 (14)
C5	0.49164 (12)	0.28101 (8)	0.31110 (6)	0.01749 (15)
C6	0.61659 (13)	0.38110 (8)	0.31980 (7)	0.02166 (17)
H6	0.613973	0.411847	0.275667	0.026*
C7	0.74526 (13)	0.43615 (8)	0.39303 (7)	0.02283 (18)
H7	0.828671	0.504994	0.398958	0.027*
C8	0.75279 (12)	0.39143 (7)	0.45739 (6)	0.01894 (16)
H8	0.840912	0.429363	0.507151	0.023*
C9	0.34619 (13)	0.03990 (8)	0.30589 (6)	0.02063 (16)
H9A	0.266099	−0.022038	0.316964	0.031*
H9B	0.457253	0.027063	0.301213	0.031*
H9C	0.298159	0.045034	0.252128	0.031*
C10	0.34774 (15)	0.26519 (11)	0.17551 (7)	0.0288 (2)
H10A	0.247916	0.215008	0.130545	0.043*
H10B	0.453296	0.271712	0.151302	0.043*
H10C	0.334288	0.338809	0.198379	0.043*
C11	0.78013 (10)	0.01095 (7)	0.41738 (5)	0.01290 (13)
C12	0.77031 (10)	−0.04677 (7)	0.47494 (5)	0.01369 (13)
H12	0.730021	−0.021214	0.526810	0.016*
C13	0.81964 (11)	−0.14140 (7)	0.45591 (6)	0.01522 (14)
H13	0.814229	−0.180789	0.494720	0.018*
C14	0.87724 (11)	−0.17801 (7)	0.37917 (6)	0.01531 (14)
C15	0.88686 (11)	−0.12229 (7)	0.32107 (6)	0.01720 (15)
H15	0.925946	−0.148619	0.268961	0.021*
C16	0.83798 (12)	−0.02699 (7)	0.34081 (6)	0.01643 (14)
H16	0.844063	0.012369	0.301954	0.020*
Cl4	0.87637 (4)	0.07775 (2)	−0.06471 (2)	0.02627 (5)
Cl5	0.82442 (3)	0.22427 (2)	−0.15224 (2)	0.02417 (5)
Cl6	0.64871 (3)	0.84635 (2)	0.08704 (2)	0.02619 (5)
O3	1.06237 (8)	0.39299 (5)	0.15401 (4)	0.01643 (11)
O4	1.08535 (9)	0.35191 (6)	0.30450 (4)	0.02088 (13)
N3	0.77232 (10)	0.36141 (6)	0.00963 (5)	0.01578 (13)
N4	0.72217 (10)	0.41370 (6)	0.07466 (5)	0.01555 (13)
C17	0.80095 (11)	0.26384 (7)	0.01445 (5)	0.01528 (14)
C18	0.82960 (12)	0.19689 (8)	−0.05837 (6)	0.01803 (15)
C19	0.80494 (11)	0.23840 (7)	0.09495 (5)	0.01545 (14)
C20	0.93752 (11)	0.30709 (7)	0.16454 (5)	0.01428 (14)
C21	0.94769 (12)	0.28288 (7)	0.24077 (5)	0.01667 (15)
C22	0.81979 (13)	0.19287 (8)	0.24688 (6)	0.02044 (17)
H22	0.823347	0.177453	0.298738	0.025*
C23	0.68692 (13)	0.12549 (8)	0.17728 (7)	0.02210 (17)
H23	0.600506	0.064214	0.182018	0.027*
C24	0.67918 (12)	0.14677 (8)	0.10112 (6)	0.01977 (16)
H24	0.589309	0.099575	0.053525	0.024*
C25	1.07785 (14)	0.50288 (8)	0.21075 (6)	0.02244 (17)
H25A	1.155871	0.558731	0.192716	0.034*
H25B	1.124324	0.512107	0.269563	0.034*
H25C	0.963877	0.512497	0.208544	0.034*
C26	1.11744 (14)	0.31627 (10)	0.37516 (6)	0.02507 (19)
H26A	1.226263	0.367450	0.413125	0.038*
H26B	1.125226	0.241010	0.353401	0.038*
H26C	1.022764	0.315986	0.407247	0.038*
C27	0.70345 (11)	0.51546 (7)	0.07168 (5)	0.01464 (14)
C28	0.76452 (12)	0.56438 (7)	0.01249 (6)	0.01693 (15)
H28	0.818802	0.528373	−0.030412	0.020*
C29	0.74563 (12)	0.66564 (8)	0.01657 (6)	0.01828 (15)
H29	0.786462	0.699392	−0.023503	0.022*
C30	0.66612 (12)	0.71729 (7)	0.08007 (6)	0.01769 (15)
C31	0.60443 (13)	0.66986 (8)	0.13918 (6)	0.02090 (17)
H31	0.549572	0.705915	0.181751	0.025*
C32	0.62434 (12)	0.56855 (8)	0.13499 (6)	0.01901 (16)
H32	0.583913	0.535295	0.175387	0.023*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.02007 (9)	0.01638 (9)	0.02093 (9)	0.00975 (7)	0.00648 (7)	0.00359 (7)
Cl2	0.01901 (9)	0.02017 (9)	0.01194 (8)	0.00688 (7)	0.00406 (6)	0.00578 (7)
Cl3	0.02032 (9)	0.01497 (9)	0.03167 (11)	0.00974 (7)	0.00761 (8)	0.00779 (8)
O1	0.0172 (3)	0.0169 (3)	0.0139 (3)	0.0034 (2)	0.0043 (2)	0.0062 (2)
O2	0.0260 (3)	0.0327 (4)	0.0171 (3)	0.0146 (3)	0.0051 (2)	0.0154 (3)
N1	0.0155 (3)	0.0132 (3)	0.0131 (3)	0.0058 (2)	0.0034 (2)	0.0045 (2)
N2	0.0166 (3)	0.0132 (3)	0.0140 (3)	0.0064 (2)	0.0046 (2)	0.0055 (2)
C1	0.0138 (3)	0.0122 (3)	0.0130 (3)	0.0046 (3)	0.0029 (2)	0.0044 (3)
C2	0.0141 (3)	0.0136 (3)	0.0146 (3)	0.0056 (3)	0.0032 (3)	0.0038 (3)
C3	0.0164 (3)	0.0136 (3)	0.0158 (3)	0.0074 (3)	0.0060 (3)	0.0070 (3)
C4	0.0164 (3)	0.0155 (3)	0.0153 (3)	0.0077 (3)	0.0063 (3)	0.0081 (3)
C5	0.0209 (4)	0.0230 (4)	0.0178 (4)	0.0137 (3)	0.0087 (3)	0.0124 (3)
C6	0.0275 (4)	0.0234 (4)	0.0274 (4)	0.0155 (4)	0.0144 (4)	0.0181 (4)
C7	0.0256 (4)	0.0167 (4)	0.0328 (5)	0.0083 (3)	0.0123 (4)	0.0147 (4)
C8	0.0196 (4)	0.0144 (4)	0.0240 (4)	0.0053 (3)	0.0066 (3)	0.0078 (3)
C9	0.0261 (4)	0.0180 (4)	0.0150 (4)	0.0042 (3)	0.0031 (3)	0.0049 (3)
C10	0.0344 (5)	0.0474 (6)	0.0228 (4)	0.0253 (5)	0.0113 (4)	0.0245 (5)
C11	0.0150 (3)	0.0122 (3)	0.0131 (3)	0.0056 (3)	0.0041 (2)	0.0052 (3)
C12	0.0151 (3)	0.0139 (3)	0.0134 (3)	0.0051 (3)	0.0038 (3)	0.0059 (3)
C13	0.0151 (3)	0.0143 (3)	0.0177 (4)	0.0050 (3)	0.0029 (3)	0.0074 (3)
C14	0.0143 (3)	0.0119 (3)	0.0207 (4)	0.0056 (3)	0.0042 (3)	0.0056 (3)
C15	0.0199 (4)	0.0161 (4)	0.0176 (4)	0.0079 (3)	0.0078 (3)	0.0057 (3)
C16	0.0218 (4)	0.0159 (4)	0.0150 (3)	0.0083 (3)	0.0076 (3)	0.0070 (3)
Cl4	0.04214 (14)	0.02113 (10)	0.01987 (10)	0.01977 (10)	0.00606 (9)	0.00440 (8)
Cl5	0.03724 (12)	0.02648 (11)	0.01195 (9)	0.01681 (9)	0.00405 (8)	0.00530 (8)
Cl6	0.02955 (11)	0.01739 (10)	0.03471 (13)	0.01311 (9)	0.00505 (9)	0.00860 (9)
O3	0.0186 (3)	0.0153 (3)	0.0166 (3)	0.0047 (2)	0.0048 (2)	0.0075 (2)
O4	0.0265 (3)	0.0255 (3)	0.0147 (3)	0.0114 (3)	0.0034 (2)	0.0101 (2)
N3	0.0188 (3)	0.0153 (3)	0.0143 (3)	0.0077 (3)	0.0029 (2)	0.0049 (2)
N4	0.0173 (3)	0.0153 (3)	0.0157 (3)	0.0072 (2)	0.0038 (2)	0.0056 (2)
C17	0.0176 (3)	0.0142 (3)	0.0144 (3)	0.0065 (3)	0.0025 (3)	0.0045 (3)
C18	0.0236 (4)	0.0175 (4)	0.0139 (3)	0.0100 (3)	0.0023 (3)	0.0040 (3)
C19	0.0197 (4)	0.0142 (3)	0.0152 (3)	0.0080 (3)	0.0057 (3)	0.0061 (3)
C20	0.0181 (3)	0.0139 (3)	0.0145 (3)	0.0079 (3)	0.0058 (3)	0.0068 (3)
C21	0.0231 (4)	0.0182 (4)	0.0148 (3)	0.0119 (3)	0.0073 (3)	0.0083 (3)
C22	0.0304 (4)	0.0193 (4)	0.0213 (4)	0.0140 (3)	0.0140 (3)	0.0126 (3)
C23	0.0288 (4)	0.0151 (4)	0.0275 (4)	0.0087 (3)	0.0143 (4)	0.0106 (3)
C24	0.0226 (4)	0.0139 (4)	0.0225 (4)	0.0055 (3)	0.0069 (3)	0.0056 (3)
C25	0.0292 (5)	0.0150 (4)	0.0197 (4)	0.0048 (3)	−0.0016 (3)	0.0051 (3)
C26	0.0324 (5)	0.0386 (6)	0.0165 (4)	0.0223 (4)	0.0088 (3)	0.0153 (4)
C27	0.0163 (3)	0.0149 (3)	0.0133 (3)	0.0064 (3)	0.0026 (3)	0.0046 (3)
C28	0.0215 (4)	0.0174 (4)	0.0153 (3)	0.0095 (3)	0.0062 (3)	0.0067 (3)
C29	0.0226 (4)	0.0176 (4)	0.0177 (4)	0.0089 (3)	0.0047 (3)	0.0079 (3)
C30	0.0187 (4)	0.0143 (3)	0.0201 (4)	0.0077 (3)	0.0013 (3)	0.0044 (3)
C31	0.0247 (4)	0.0196 (4)	0.0210 (4)	0.0116 (3)	0.0088 (3)	0.0055 (3)
C32	0.0240 (4)	0.0192 (4)	0.0172 (4)	0.0101 (3)	0.0087 (3)	0.0069 (3)

Geometric parameters (Å, º) top

Cl1—C2	1.7161 (9)	Cl4—C18	1.7151 (9)
Cl2—C2	1.7149 (9)	Cl5—C18	1.7159 (9)
Cl3—C14	1.7379 (9)	Cl6—C30	1.7397 (9)
O1—C4	1.3753 (10)	O3—C20	1.3755 (10)
O1—C9	1.4401 (11)	O3—C25	1.4418 (12)
O2—C5	1.3601 (12)	O4—C21	1.3650 (12)
O2—C10	1.4325 (12)	O4—C26	1.4340 (11)
N1—N2	1.2646 (10)	N3—N4	1.2649 (10)
N1—C1	1.4139 (11)	N3—C17	1.4134 (11)
N2—C11	1.4277 (11)	N4—C27	1.4263 (11)
C1—C2	1.3498 (11)	C17—C18	1.3497 (12)
C1—C3	1.4846 (11)	C17—C19	1.4848 (12)
C3—C4	1.3915 (12)	C19—C20	1.3933 (12)
C3—C8	1.4004 (12)	C19—C24	1.4000 (12)
C4—C5	1.4096 (12)	C20—C21	1.4084 (12)
C5—C6	1.3943 (14)	C21—C22	1.3938 (13)
C6—C7	1.3930 (15)	C22—C23	1.3916 (15)
C6—H6	0.9500	C22—H22	0.9500
C7—C8	1.3869 (13)	C23—C24	1.3863 (14)
C7—H7	0.9500	C23—H23	0.9500
C8—H8	0.9500	C24—H24	0.9500
C9—H9A	0.9800	C25—H25A	0.9800
C9—H9B	0.9800	C25—H25B	0.9800
C9—H9C	0.9800	C25—H25C	0.9800
C10—H10A	0.9800	C26—H26A	0.9800
C10—H10B	0.9800	C26—H26B	0.9800
C10—H10C	0.9800	C26—H26C	0.9800
C11—C16	1.3959 (11)	C27—C32	1.3961 (12)
C11—C12	1.4012 (11)	C27—C28	1.3978 (12)
C12—C13	1.3875 (12)	C28—C29	1.3868 (12)
C12—H12	0.9500	C28—H28	0.9500
C13—C14	1.3942 (12)	C29—C30	1.3929 (13)
C13—H13	0.9500	C29—H29	0.9500
C14—C15	1.3891 (12)	C30—C31	1.3863 (13)
C15—C16	1.3934 (12)	C31—C32	1.3904 (13)
C15—H15	0.9500	C31—H31	0.9500
C16—H16	0.9500	C32—H32	0.9500

C4—O1—C9	117.08 (7)	C20—O3—C25	115.29 (7)
C5—O2—C10	117.18 (8)	C21—O4—C26	116.79 (8)
N2—N1—C1	113.70 (7)	N4—N3—C17	113.56 (7)
N1—N2—C11	113.47 (7)	N3—N4—C27	113.24 (7)
C2—C1—N1	115.71 (7)	C18—C17—N3	115.51 (8)
C2—C1—C3	121.82 (7)	C18—C17—C19	122.16 (8)
N1—C1—C3	122.46 (7)	N3—C17—C19	122.30 (7)
C1—C2—Cl2	123.13 (7)	C17—C18—Cl4	122.85 (7)
C1—C2—Cl1	122.29 (7)	C17—C18—Cl5	122.94 (7)
Cl2—C2—Cl1	114.57 (5)	Cl4—C18—Cl5	114.21 (5)
C4—C3—C8	120.33 (8)	C20—C19—C24	120.27 (8)
C4—C3—C1	118.81 (7)	C20—C19—C17	118.74 (8)
C8—C3—C1	120.86 (8)	C24—C19—C17	120.99 (8)
O1—C4—C3	117.55 (7)	O3—C20—C19	118.06 (7)
O1—C4—C5	122.34 (8)	O3—C20—C21	121.82 (8)
C3—C4—C5	119.88 (8)	C19—C20—C21	119.96 (8)
O2—C5—C6	125.08 (8)	O4—C21—C22	124.62 (8)
O2—C5—C4	115.52 (8)	O4—C21—C20	116.11 (8)
C6—C5—C4	119.40 (9)	C22—C21—C20	119.27 (8)
C7—C6—C5	120.18 (8)	C23—C22—C21	120.24 (8)
C7—C6—H6	119.9	C23—C22—H22	119.9
C5—C6—H6	119.9	C21—C22—H22	119.9
C8—C7—C6	120.65 (9)	C24—C23—C22	120.76 (9)
C8—C7—H7	119.7	C24—C23—H23	119.6
C6—C7—H7	119.7	C22—C23—H23	119.6
C7—C8—C3	119.53 (9)	C23—C24—C19	119.44 (9)
C7—C8—H8	120.2	C23—C24—H24	120.3
C3—C8—H8	120.2	C19—C24—H24	120.3
O1—C9—H9A	109.5	O3—C25—H25A	109.5
O1—C9—H9B	109.5	O3—C25—H25B	109.5
H9A—C9—H9B	109.5	H25A—C25—H25B	109.5
O1—C9—H9C	109.5	O3—C25—H25C	109.5
H9A—C9—H9C	109.5	H25A—C25—H25C	109.5
H9B—C9—H9C	109.5	H25B—C25—H25C	109.5
O2—C10—H10A	109.5	O4—C26—H26A	109.5
O2—C10—H10B	109.5	O4—C26—H26B	109.5
H10A—C10—H10B	109.5	H26A—C26—H26B	109.5
O2—C10—H10C	109.5	O4—C26—H26C	109.5
H10A—C10—H10C	109.5	H26A—C26—H26C	109.5
H10B—C10—H10C	109.5	H26B—C26—H26C	109.5
C16—C11—C12	120.20 (7)	C32—C27—C28	120.14 (8)
C16—C11—N2	115.60 (7)	C32—C27—N4	115.82 (8)
C12—C11—N2	124.20 (7)	C28—C27—N4	123.99 (8)
C13—C12—C11	119.76 (8)	C29—C28—C27	119.81 (8)
C13—C12—H12	120.1	C29—C28—H28	120.1
C11—C12—H12	120.1	C27—C28—H28	120.1
C12—C13—C14	119.25 (8)	C28—C29—C30	119.25 (8)
C12—C13—H13	120.4	C28—C29—H29	120.4
C14—C13—H13	120.4	C30—C29—H29	120.4
C15—C14—C13	121.82 (8)	C31—C30—C29	121.72 (8)
C15—C14—Cl3	118.73 (7)	C31—C30—Cl6	119.16 (7)
C13—C14—Cl3	119.44 (7)	C29—C30—Cl6	119.09 (7)
C14—C15—C16	118.62 (8)	C30—C31—C32	118.77 (8)
C14—C15—H15	120.7	C30—C31—H31	120.6
C16—C15—H15	120.7	C32—C31—H31	120.6
C15—C16—C11	120.35 (8)	C31—C32—C27	120.30 (8)
C15—C16—H16	119.8	C31—C32—H32	119.8
C11—C16—H16	119.8	C27—C32—H32	119.8

C1—N1—N2—C11	−179.49 (7)	C17—N3—N4—C27	176.47 (7)
N2—N1—C1—C2	−175.87 (7)	N4—N3—C17—C18	170.57 (8)
N2—N1—C1—C3	4.67 (11)	N4—N3—C17—C19	−11.33 (12)
N1—C1—C2—Cl2	1.60 (11)	N3—C17—C18—Cl4	177.08 (6)
C3—C1—C2—Cl2	−178.94 (6)	C19—C17—C18—Cl4	−1.02 (13)
N1—C1—C2—Cl1	−177.06 (6)	N3—C17—C18—Cl5	−2.27 (12)
C3—C1—C2—Cl1	2.41 (12)	C19—C17—C18—Cl5	179.62 (7)
C2—C1—C3—C4	−108.12 (10)	C18—C17—C19—C20	112.01 (10)
N1—C1—C3—C4	71.31 (10)	N3—C17—C19—C20	−65.97 (11)
C2—C1—C3—C8	72.24 (11)	C18—C17—C19—C24	−67.47 (12)
N1—C1—C3—C8	−108.33 (10)	N3—C17—C19—C24	114.55 (10)
C9—O1—C4—C3	−121.98 (8)	C25—O3—C20—C19	119.91 (8)
C9—O1—C4—C5	63.47 (11)	C25—O3—C20—C21	−64.64 (10)
C8—C3—C4—O1	−173.36 (8)	C24—C19—C20—O3	177.05 (8)
C1—C3—C4—O1	7.00 (11)	C17—C19—C20—O3	−2.43 (11)
C8—C3—C4—C5	1.34 (12)	C24—C19—C20—C21	1.52 (12)
C1—C3—C4—C5	−178.31 (7)	C17—C19—C20—C21	−177.96 (8)
C10—O2—C5—C6	0.14 (13)	C26—O4—C21—C22	12.60 (12)
C10—O2—C5—C4	−179.98 (8)	C26—O4—C21—C20	−167.81 (8)
O1—C4—C5—O2	−5.68 (12)	O3—C20—C21—O4	2.16 (12)
C3—C4—C5—O2	179.89 (7)	C19—C20—C21—O4	177.53 (8)
O1—C4—C5—C6	174.21 (8)	O3—C20—C21—C22	−178.23 (8)
C3—C4—C5—C6	−0.23 (12)	C19—C20—C21—C22	−2.87 (12)
O2—C5—C6—C7	178.86 (9)	O4—C21—C22—C23	−178.23 (8)
C4—C5—C6—C7	−1.01 (13)	C20—C21—C22—C23	2.20 (13)
C5—C6—C7—C8	1.15 (14)	C21—C22—C23—C24	−0.17 (14)
C6—C7—C8—C3	−0.04 (14)	C22—C23—C24—C19	−1.20 (14)
C4—C3—C8—C7	−1.20 (13)	C20—C19—C24—C23	0.52 (13)
C1—C3—C8—C7	178.43 (8)	C17—C19—C24—C23	179.99 (8)
N1—N2—C11—C16	−178.41 (7)	N3—N4—C27—C32	170.83 (8)
N1—N2—C11—C12	2.04 (12)	N3—N4—C27—C28	−11.65 (12)
C16—C11—C12—C13	0.52 (12)	C32—C27—C28—C29	−0.28 (13)
N2—C11—C12—C13	−179.95 (8)	N4—C27—C28—C29	−177.70 (8)
C11—C12—C13—C14	−0.45 (12)	C27—C28—C29—C30	0.17 (13)
C12—C13—C14—C15	0.06 (13)	C28—C29—C30—C31	−0.33 (14)
C12—C13—C14—Cl3	−179.04 (6)	C28—C29—C30—Cl6	178.02 (7)
C13—C14—C15—C16	0.28 (13)	C29—C30—C31—C32	0.58 (14)
Cl3—C14—C15—C16	179.39 (7)	Cl6—C30—C31—C32	−177.77 (7)
C14—C15—C16—C11	−0.22 (13)	C30—C31—C32—C27	−0.68 (14)
C12—C11—C16—C15	−0.17 (13)	C28—C27—C32—C31	0.54 (14)
N2—C11—C16—C15	−179.74 (8)	N4—C27—C32—C31	178.16 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9C···O2	0.98	2.32	2.9059 (12)	117
C10—H10C···O3ⁱ	0.98	2.65	3.3241 (13)	126
C12—H12···O1ⁱⁱ	0.95	2.66	3.2919 (11)	125
C25—H25B···O4	0.98	2.33	2.9226 (12)	118
C25—H25C···N4	0.98	2.58	3.2210 (13)	124
C31—H31···Cl2ⁱⁱⁱ	0.95	2.87	3.7991 (10)	166

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

Acknowledgements

The contributions of the authors are as follows: conceptualization NQS, MA and GTA; synthesis NAM, PAH, GVB; X-ray analysis MA, GAM; writing (review and editing of the manuscript) MA, NQS and GTA; funding acquisition AB, NQS and PAH; supervision NQS and MA.

References

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

Syntheses, crystal structures and Hirshfeld surface analyses of (E)-1-[2,2-di­chloro-1-(2,3-di­meth­oxyphen­yl)ethen-1-yl]-2-phenyl­diazene and (E)-1-(4-chloro­phen­yl)-2-[2,2-di­chloro-1-(2,3-di­meth­­oxy­phen­yl)ethen-1-yl]diazene

1. Chemical context

2. Structural commentary

3. Supra­molecular features and Hirshfeld surface analyses

4. Database survey

5. Synthesis and crystallization

6. Refinement

Supporting information

Acknowledgements

References

research communications

Syntheses, crystal structures and Hirshfeld surface analyses of (E)-1-[2,2-dichloro-1-(2,3-dimethoxyphenyl)ethen-1-yl]-2-phenyldiazene and (E)-1-(4-chlorophenyl)-2-[2,2-dichloro-1-(2,3-dimethoxyphenyl)ethen-1-yl]diazene

3. Supramolecular features and Hirshfeld surface analyses