The crystal structures and Hirshfeld surface analyses of two similar azo compounds are reported. In the first, 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. In the other, the 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.
Keywords: crystal structure, C—H⋯π interactions, C—Cl⋯π interactions, van der Waals interactions, Hirshfeld surface analysis
Abstract
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.
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.
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.
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) 
.
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.
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)].
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) .
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⋯Cg2a: C2—Cl2 = 1.7131 (15) Å, Cl2⋯Cg2a = 3.9882 (7) Å, C2⋯Cg2a = 4.2031 (16) Å, C2—Cl2⋯Cg2a = 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⋯Cg2b: C2—Cl2 = 1.7149 (9) Å, Cl2⋯Cg2b = 3.4334 (7) Å, C2⋯Cg2b = 3.7761 (11) Å, C2—Cl2⋯Cg2b = 87.72 (3), and C18—Cl5⋯Cg4c: C18—Cl5 = 1.7159 (9) Å, Cl5⋯Cg4c = 3.8775 (7) Å, C18⋯Cg4c = 4.1527 (13) Å, C18—Cl5⋯Cg4c = 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 dnorm 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. 9 ▸a for (I) and Fig. 9 ▸c,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 dnorm.
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 di and de 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 (
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 Uiso(H) = 1.2 or 1.5 Ueq(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
|
| 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 ▸) |
| Tmin, Tmax | 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 |
| Δρmax, Δρmin (e Å−3) | 0.33, −0.36 | 0.48, −0.36 |
Supplementary Material
Crystal structure: contains datablock(s) I, II. DOI: 10.1107/S2056989026000137/nx2031sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989026000137/nx2031Isup2.hkl
Structure factors: contains datablock(s) II. DOI: 10.1107/S2056989026000137/nx2031IIsup3.hkl
Additional supporting information: crystallographic information; 3D view; checkCIF report
Acknowledgments
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.
supplementary crystallographic information
(E)-1-[2,2-Dichloro-1-(2,3-dimethoxyphenyl)ethen-1-yl]-2-phenyldiazene (I) . Crystal data
| C16H14Cl2N2O2 | F(000) = 696 |
| Mr = 337.19 | Dx = 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 |
(E)-1-[2,2-Dichloro-1-(2,3-dimethoxyphenyl)ethen-1-yl]-2-phenyldiazene (I) . Data collection
| Rigaku XtaLAB Synergy-S, HyPix-6000HE area-detector diffractometer | 3376 reflections with I > 2σ(I) |
| Radiation source: micro-focus sealed X-ray tube | Rint = 0.046 |
| φ and ω scans | θmax = 80.0°, θmin = 2.9° |
| Absorption correction: gaussian (CrysAlisPro; Rigaku OD, 2025) | h = −9→9 |
| Tmin = 0.641, Tmax = 0.796 | k = −39→39 |
| 81705 measured reflections | l = −9→9 |
| 3424 independent reflections |
(E)-1-[2,2-Dichloro-1-(2,3-dimethoxyphenyl)ethen-1-yl]-2-phenyldiazene (I) . Refinement
| 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(Fo2) + (0.0377P)2 + 1.1051P] where P = (Fo2 + 2Fc2)/3 |
| 3424 reflections | (Δ/σ)max = 0.001 |
| 201 parameters | Δρmax = 0.33 e Å−3 |
| 0 restraints | Δρmin = −0.36 e Å−3 |
(E)-1-[2,2-Dichloro-1-(2,3-dimethoxyphenyl)ethen-1-yl]-2-phenyldiazene (I) . Special details
| 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. |
(E)-1-[2,2-Dichloro-1-(2,3-dimethoxyphenyl)ethen-1-yl]-2-phenyldiazene (I) . Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| 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* |
(E)-1-[2,2-Dichloro-1-(2,3-dimethoxyphenyl)ethen-1-yl]-2-phenyldiazene (I) . Atomic displacement parameters (Å2)
| 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) |
(E)-1-[2,2-Dichloro-1-(2,3-dimethoxyphenyl)ethen-1-yl]-2-phenyldiazene (I) . Geometric parameters (Å, º)
| 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) |
(E)-1-[2,2-Dichloro-1-(2,3-dimethoxyphenyl)ethen-1-yl]-2-phenyldiazene (I) . Hydrogen-bond geometry (Å, º)
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) . Crystal data
| C16H13Cl3N2O2 | Z = 4 |
| Mr = 371.63 | F(000) = 760 |
| Triclinic, P1 | Dx = 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 |
(E)-1-(4-Chlorophenyl)-2-[2,2-dichloro-1-(2,3-dimethoxyphenyl)ethen-1-yl]diazene (II) . Data collection
| Bruker D8 QUEST PHOTON-III area detector diffractometer | 10714 reflections with I > 2σ(I) |
| Radiation source: fine-focus sealed X-ray tube | Rint = 0.023 |
| φ and ω scans | θmax = 32.6°, θmin = 2.5° |
| Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −12→12 |
| Tmin = 0.656, Tmax = 0.746 | k = −20→20 |
| 39419 measured reflections | l = −25→25 |
| 11888 independent reflections |
(E)-1-(4-Chlorophenyl)-2-[2,2-dichloro-1-(2,3-dimethoxyphenyl)ethen-1-yl]diazene (II) . Refinement
| 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(Fo2) + (0.0326P)2 + 0.5553P] where P = (Fo2 + 2Fc2)/3 |
| 11888 reflections | (Δ/σ)max = 0.002 |
| 419 parameters | Δρmax = 0.48 e Å−3 |
| 0 restraints | Δρmin = −0.36 e Å−3 |
(E)-1-(4-Chlorophenyl)-2-[2,2-dichloro-1-(2,3-dimethoxyphenyl)ethen-1-yl]diazene (II) . Special details
| 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. |
(E)-1-(4-Chlorophenyl)-2-[2,2-dichloro-1-(2,3-dimethoxyphenyl)ethen-1-yl]diazene (II) . Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| 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* |
(E)-1-(4-Chlorophenyl)-2-[2,2-dichloro-1-(2,3-dimethoxyphenyl)ethen-1-yl]diazene (II) . Atomic displacement parameters (Å2)
| 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) |
(E)-1-(4-Chlorophenyl)-2-[2,2-dichloro-1-(2,3-dimethoxyphenyl)ethen-1-yl]diazene (II) . Geometric parameters (Å, º)
| 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) |
(E)-1-(4-Chlorophenyl)-2-[2,2-dichloro-1-(2,3-dimethoxyphenyl)ethen-1-yl]diazene (II) . Hydrogen-bond geometry (Å, º)
| 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.
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) I, II. DOI: 10.1107/S2056989026000137/nx2031sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989026000137/nx2031Isup2.hkl
Structure factors: contains datablock(s) II. DOI: 10.1107/S2056989026000137/nx2031IIsup3.hkl
Additional supporting information: crystallographic information; 3D view; checkCIF report