Crystal structures and Hirshfeld surface analyses of the two isotypic compounds (E)-1-(4-bromo­phen­yl)-2-[2,2-di­chloro-1-(4-nitro­phen­yl)ethen­yl]diazene and (E)-1-(4-chloro­phen­yl)-2-[2,2-di­chloro-1-(4-nitro­phen­yl)ethen­yl]diazene

Akkurt, M.; Shikhaliyev, N.Q.; Suleymanova, G.T.; Babayeva, G.V.; Mammadova, G.Z.; Niyazova, A.A.; Shikhaliyeva, I.M.; Toze, F.A.A.

doi:10.1107/S2056989019010004

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ISSN: 2056-9890

Volume 75| Part 8| August 2019| Pages 1199-1204

https://doi.org/10.1107/S2056989019010004

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Crystal structures and Hirshfeld surface analyses of the two isotypic compounds (E)-1-(4-bromophenyl)-2-[2,2-dichloro-1-(4-nitrophenyl)ethenyl]diazene and (E)-1-(4-chlorophenyl)-2-[2,2-dichloro-1-(4-nitrophenyl)ethenyl]diazene

Mehmet Akkurt,^a Namiq Q. Shikhaliyev,^b Gulnar T. Suleymanova,^b Gulnare V. Babayeva,^b Gunay Z. Mammadova,^b Ayten A. Niyazova,^b Irada M. Shikhaliyeva ^b and Flavien A. A. Toze ^c ^*

^aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^bOrganic Chemistry Department, Baku State University, Z. Xalilov str. 23, Az, 1148 Baku, Azerbaijan, and ^cDepartment of Chemistry, Faculty of Sciences, University of Douala, PO Box 24157, Douala, Republic of , Cameroon
^*Correspondence e-mail: toflavien@yahoo.fr

Edited by M. Weil, Vienna University of Technology, Austria (Received 16 May 2019; accepted 12 July 2019; online 19 July 2019)

In the two isotypic title compounds, C₁₄H₈BrCl₂N₃O₂, (I), and C₁₄H₈Cl₃N₃O₂, (II), the substitution of one of the phenyl rings is different [Br for (I) and Cl for (II)]. Aromatic rings form dihedral angles of 60.9 (2) and 64.1 (2)°, respectively. Molecules are linked through weak X⋯Cl contacts [X = Br for (I) and Cl for (II)], C—H⋯Cl and C—Cl⋯π interactions into sheets parallel to the ab plane. Additional van der Waals interactions consolidate the three-dimensional packing. Hirshfeld surface analysis of the crystal structures indicates that the most important contributions for the crystal packing for (I) are from C⋯H/H⋯C (16.1%), O⋯H/H⋯O (13.1%), Cl⋯H/H⋯Cl (12.7%), H⋯H (11.4%), Br⋯H/H⋯Br (8.9%), N⋯H/H⋯N (6.9%) and Cl⋯C/C⋯Cl (6.6%) interactions, and for (II), from Cl⋯H / H⋯Cl (21.9%), C⋯H/H⋯C (15.3%), O⋯H/H⋯O (13.4%), H⋯H (11.5%), Cl⋯C/C⋯Cl (8.3%), N⋯H/H⋯N (7.0%) and Cl⋯Cl (5.9%) interactions. The crystal of (I) studied was refined as an inversion twin, the ratio of components being 0.9917 (12):0.0083 (12).

Keywords: crystal structure; diazene derivatives; dyes; intermolecular halogen bonds; Hirshfeld surface analysis.

CCDC references: 1940144; 1940145

1. Chemical context

Compounds with azo/hydrazone moieties are ubiquitous in various fields, ranging from organic/inorganic synthesis, catalysis, and medicinal chemistry to material chemistry. They are used as dyes, ligands, solvatochromic materials, molecular switches, or analytical reagents amongst other applications (Akbari et al., 2017 ; Asadov et al., 2016 ; Gurbanov et al., 2018 ; Kopylovich et al., 2011 ; Ma et al., 2017 ; Mahmoudi et al., 2018 ; Mahmudov et al., 2014 , 2019 ).

The non-covalent donor/acceptor properties of azo/hydrazones depend strongly on the attached functional groups (Shixaliyev et al., 2013 , 2014 , 2018 ). In a previous study we have attached halogen atoms to dye molecules, which led to halogen bonding (Maharramov et al., 2018 ; Shixaliyev et al., 2018). In a continuation of our work in this direction, we have now synthesized two new azo dyes, (E)-1-(4-bromophenyl)-2-(2,2-dichloro-1-(4-nitrophenyl)vinyl)diazene (I) and (E)-1-(4-chlorophenyl)-2-(2,2-dichloro-1-(4-nitrophenyl)vinyl)diazene (II), and report here their molecular and crystal structures.

2. Structural commentary

Compounds (I) and (II) are isotypic. Their molecular structures (Figs. 1 and 2) are not planar. For the bromo-substituted compound (I), the dihedral angle between the essentially planar 4-bromophenyl ring C1–C6 [maximum deviation = 0.015 (6) Å at atom C5] and the nitro-substituted benzene ring C9–C14 [maximum deviation = −0.009 (4) Å at atom C9] is 60.9 (2)°, for the chloro-substituted compound (II) the corresponding value is 64.1 (2)°. The torsion angles involving the central diazene group amount to 18.3 (6)° for C2—C1—N1—N2, −179.1 (3)° for C1—N1—N2—C7, and 175.4 (4)° for N1—N2—C7—C8 for (I). The corresponding values for (II) are −17.0 (5)°, 179.0 (3)° and 175.4 (4)°, respectively. The bond lengths and angles are within normal ranges and are comparable to those in the related structures detailed in the Database survey.

Figure 1
The molecular structure of (I)

with displacement ellipsoids drawn at the 30% probability level.

Figure 2
The molecular structure of (II)

with displacement ellipsoids drawn at the 30% probability level.

3. Supramolecular features and Hirshfeld surface analysis

As a result of the isotypism of (I) and (II), the packing features are generally very similar in the two structures. Molecules are linked by weak Br⋯Cl contacts [for (I)] or Cl⋯Cl contacts [for (II)] and C—H⋯Cl interactions into chains extending along the a-axis direction (Tables 1–3 ; Figs. 3 and 4). Additional C—Cl⋯π interactions lead to the formation of sheets parallel to the ab plane (Fig. 5). van der Waals interactions (Table 3) consolidate the three-dimensional packing.

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

Cg2 is the centroid of the C9–C14 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯Cl2ⁱ	0.93	2.92	3.593 (5)	131
C8—Cl2⋯Cg2ⁱⁱ	1.71 (1)	3.66 (1)	4.710 (5)	118 (1)
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z]$ .

Table 2
C—Cl⋯π geometry (Å, °) for (II)

Cg2 is the centroid of the C9–C14 ring.

C—C⋯π	C—Cl	Cl⋯π	C⋯π	C—C⋯π
C8—Cl3⋯Cg2ⁱ	1.71 (1)	3.62 (1)	4.703 (3)	120 (1)
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ .

Table 3
Summary of short interatomic contacts (Å) in the crystal structures of compounds (I) and (II)

Contact	Distance	Symmetry operation
Compound (I)
H10⋯Br1	3.18	1 − x, 1 − y, $[{1\over 2}]$ + z
Br1⋯Cl1	3.5125 (12)	$[{1\over 2}]$ + x, $[{1\over 2}]$ − y, z
H2⋯H11	2.54	$[{1\over 2}]$ − x, − $[{1\over 2}]$ + y, − $[{1\over 2}]$ + z
Cl2⋯H6	2.92	− $[{1\over 2}]$ + x, $[{3\over 2}]$ − y, z
O2⋯H3	2.68	x, 1 + y, z
H13⋯N2	2.73	$[{1\over 2}]$ − x, $[{1\over 2}]$ + y, − $[{1\over 2}]$ + z
Compound (II)
H10⋯Cl1	3.13	2 − x, −y, − $[{1\over 2}]$ + z
Cl1⋯Cl2	3.4847 (14)	$[{1\over 2}]$ + x, − $[{1\over 2}]$ − y, z
H2⋯H11	2.56	$[{3\over 2}]$ − x, − $[{1\over 2}]$ + y, $[{1\over 2}]$ + z
Cl3⋯H6	2.98	− $[{1\over 2}]$ + x, $[{1\over 2}]$ − y, z
O2⋯H3	2.66	x, 1 + y, z
H13⋯N2	2.69	$[{3\over 2}]$ − x, $[{1\over 2}]$ + y, $[{1\over 2}]$ + z

Figure 3
Packing in the crystal structure of (I)

showing chains running parallel to the a-axis.

Figure 4
A view of the packing in (I)

along the a axis showing C—H⋯Cl contacts.

Figure 5
Formation of sheets in (II)

parallel to ab through C—Cl⋯π contacts.

Hirshfeld surface analysis (Spackman & Jayatilaka, 2009 ) was used to investigate the intermolecular interactions in the crystal structures of both compounds (CrystalExplorer3.1; Wolff et al., 2012 ). The surface plots (Spackman et al., 2008 ) mapped over d_norm were generated to quantify and visualize the intermolecular interactions and to explain the observed crystal packing. Dark-red spots on the d_norm surface arise as a result of short interatomic contacts (Tables 1–3 ), while the other weaker intermolecular interactions appear as light-red spots.

For (I), the red points, which represent closer contacts and negative d_norm values on the surface, correspond to the C—H⋯O interactions. The reciprocal O⋯H/H⋯O interactions appear as two symmetrical broad wings in the two-dimensional fingerprint plots with d_e + d_i ≃ 2.5 Å and contribute 13.1% to the Hirshfeld surface (Fig. 6b). The reciprocal Cl⋯H/H⋯Cl interaction with a contribution of 13.8% is present as sharp symmetrical spikes at d_e + d_i ≃ 2.8 Å (Fig. 6c).

Figure 6
Hirshfeld surface representations and full two-dimensional fingerprint plots for (I)

, showing (a) all interactions, and delineated into (b) C⋯H/H⋯C (c), O⋯H/H⋯O (d), Cl⋯H/H⋯Cl (e), H⋯H (f), Br⋯H/H⋯Br (g), N⋯H/H⋯N and (h) Cl⋯C/C⋯Cl interactions. The d_i and d_e values are the closest internal and external distances (in Å) from a given point on the Hirshfeld surface.

For (II), the percentage contributions of various contacts to the total Hirshfeld surface are shown in the two-dimensional fingerprint plots in Fig. 7. The reciprocal Cl⋯H/H⋯Cl interactions appear as two symmetrical broad wings with d_e + d_i ≃ 2.9 Å and contribute 21.9% to the Hirshfeld surface (Fig. 7b). The reciprocal C⋯H/H⋯C and O⋯H/H⋯O interactions (15.3, 13.4% contributions, respectively) are present as sharp symmetrical spikes at d_e + d_i ≃ 2.95 and 2.5 Å, respectively (Fig. 7c–d). The small percentage contributions of both compounds to the Hirshfeld surfaces from the various other interatomic contacts are comparatively listed in Table 4. Although there is almost agreement on the values given for the molecules of (I) and (II), some differences are due to the different halogen atoms substituting the phenyl ring and the different molecular environment in the crystal structures.

Table 4
Percentage contributions of interatomic contacts to the Hirshfeld surface in the crystal structures of compounds (I) and (II)

Contact	(I)	(II)
C⋯H/H⋯C	16.1	15.3
O⋯H/H⋯O	13.1	13.4
Cl⋯H/H⋯Cl	12.7	21.9
H⋯H	11.4	11.5
Br⋯H/H⋯Br	8.9	–
N⋯H/H⋯N	6.9	7.0
Cl⋯C/C⋯Cl	6.6	8.3
Cl⋯Br/Br⋯Cl	5.2	–
Cl⋯O/O⋯Cl	4.9	5.8
O⋯C/C⋯O	3.8	3.9
Cl⋯N/N⋯Cl	3.4	3.4
C⋯C	2.1	2.3
Br⋯C/C⋯Br	1.5	–
Br⋯O/O⋯Br	1.2	–
N⋯O/O⋯N	1.1	1.0
Cl⋯Cl	1.0	5.9
N⋯C/C⋯N	0.1	0.2
Br⋯N/N⋯Br	0.1	–

Figure 7
The Hirshfeld surface representations and the full two-dimensional fingerprint plots for (II)

, showing (a) all interactions, and delineated into (b) Cl⋯H/H⋯Cl, (c) C⋯H/H⋯C, (d) O⋯H/H⋯O, (e) H⋯H, (f) Cl⋯C/C⋯Cl, (g) N⋯H/H⋯N and (h) Cl⋯Cl interactions. The d_i and d_e values are the closest internal and external distances (in Å) from a given point on the Hirshfeld surface.

4. Database survey

A search of the Cambridge Structural Database (CSD, Version 5.40, November 2018; Groom et al., 2016 ) for structures having an (E)-1-(2,2-dichloro-1-phenylvinyl)-2-phenyldiazene unit gave 23 hits. Four compounds closely resemble the title compound, viz. 1-(4-chlorophenyl)-2-[2,2-dichloro-1-(4-fluorophenyl)ethenyl]diazene (CSD refcode HODQAV; Shikhaliyev et al., 2019 ), 1-[2,2-dichloro-1-(4-nitrophenyl)ethenyl]-2-(4-fluorophenyl)diazene (XIZREG; Atioğlu et al., 2019 ), 1,1-[methylenebis(4,1-phenylene)]bis[(2, 2-dichloro-1-(4-nitrophenyl)ethenyl]diazene (LEQXIR; Shixaliyev et al., 2018), 1,1-[methylenebis(4,1-phenylene)]bis{[2,2-dichloro-1-(4-chlorophenyl)ethenyl]diazene} (LEQXOX; Shixaliyev et al., 2018),

In the crystal of HODQAV, molecules are stacked in columns along the a axis via weak C—H⋯Cl hydrogen bonds and face-to-face π–π stacking interactions. The crystal packing is further stabilized by short Cl⋯Cl contacts. In XIZREG, molecules are linked by C—H⋯O hydrogen bonds into zigzag chains running along the c-axis direction. The crystal packing is further stabilized by C—Cl⋯π, C—F⋯π and N—O⋯π interactions. In the crystal of LEQXIR, C—H⋯N and C—H⋯O hydrogen bonds and Cl⋯O contacts were found, and in LEQXOX, C—H⋯N and Cl⋯Cl contacts are observed.

5. Synthesis and crystallization

Dyes (I) and (II) were synthesized according to a literature protocol (Shixaliyev et al., 2018). For (I), a 20 ml screw neck vial was charged with DMSO (10 ml), (E)-1-(4-bromophenyl)-2-(4-nitrobenzylidene)hydrazine (320 mg, 1 mmol), tetramethylethylenediamine (TMEDA) (295 mg, 2.5 mmol), CuCl (2 mg, 0.02 mmol) and CCl₄ (20 mmol, 10 equiv.). After 1–3 h (until TLC analysis showed complete consumption of the corresponding Schiff base), the reaction mixture was poured into 0.01 M solution of HCl (100 ml, pH ∼2-3), and extracted with dichloromethane (3 × 20 ml). The organic phases were combined and washed with water (3 × 50 ml), brine (30 ml), dried over anhydrous Na₂SO₄ and concentrated in vacuo in a rotary evaporator. The residue was purified by column chromatography on silica gel using appropriate mixtures of hexane and dichloromethane (v/v: 3/1–1/1). An orange solid was obtained (yield 58%); mp 418 K. Analysis calculated for C₁₄H₈BrCl₂N₃O₂ (M = 401.04): C, 41.93; H, 2.01; N, 10.48; found: C, 41.87; H, 2.03; N, 10.39%. ¹H NMR (300 MHz, CDCl₃) δ 8.30 (d, 2H, J = 9.02 Hz), 7.65–7.56 (m, 4H), 7.38 (d, 2H, J = 9.24Hz). ¹³C NMR (75 MHz, CDCl₃) δ 151.26, 150.60, 147.97, 139.21, 137.18, 132.49, 131.28, 126.83, 124.72, 123.44. ESI–MS: m/z: 402.08 [M + H]⁺.

For (II), the procedure was the same as that for (I) using (E)-1-(4-chloroophenyl)-2-(4-nitrobenzylidene)hydrazine (276 mg, 1 mmol). An orange solid was obtained (yield 64%); mp 448 K. Analysis calculated for C₁₄H₈Cl₃N₃O₂ (M = 356.59): C, 47.16; H, 2.26; N, 11.78; found: C, 47.09; H, 2.23; N, 11.65%. ¹H NMR (300 MHz, CDCl3) δ 8.32–7.37 (8H, Ar). ¹³C NMR (75 MHz, CDCl₃) δ 150.91, 150.55, 147.98, 139.28, 138.22, 137.02, 131.24, 129.49, 124.52, 123.44. ESI–MS: m/z: 357.70 [M + H]+.

Compounds (I) and (II) were dissolved in dichloromethane and then left at room temperature for slow evaporation; orange crystals of both compounds suitable for X-rays started to form after ca 2 d.

6. Refinement

Crystal data collection and structure refinement details are summarized in Table 5. C-bound H atoms were constrained to ideal values with C—H = 0.93 Å and with U_iso(H) = 1.2U_eq(C). The crystal of (I) studied was refined as an inversion twin, the ratio of components being 0.9917 (12):0.0083 (12).

Table 5
Experimental details

	(I)	(II)
Crystal data
Chemical formula	C₁₄H₈BrCl₂N₃O₂	C₁₄H₈Cl₃N₃O₂
M_r	401.04	356.58
Crystal system, space group	Orthorhombic, Pna2₁	Orthorhombic, Pna2₁
Temperature (K)	296	296
a, b, c (Å)	13.9181 (7), 13.4336 (6), 8.4080 (4)	13.8689 (7), 13.3674 (7), 8.3620 (5)
V (Å³)	1572.05 (13)	1550.24 (15)
Z	4	4
Radiation type	Mo Kα	Mo Kα
μ (mm⁻¹)	2.96	0.60
Crystal size (mm)	0.19 × 0.14 × 0.08	0.17 × 0.14 × 0.07

Data collection
Diffractometer	Bruker APEXII CCD	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2003 )	Multi-scan (SADABS; Bruker, 2003)
T_min, T_max	0.608, 0.784	0.911, 0.946
No. of measured, independent and observed [I > 2σ(I)] reflections	23012, 3429, 2811	11687, 3156, 2547
R_int	0.057	0.038
(sin θ/λ)_max (Å⁻¹)	0.641	0.626

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.081, 1.02	0.037, 0.091, 1.04
No. of reflections	3429	3156
No. of parameters	200	199
No. of restraints	1	1
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.50	0.18, −0.25
Absolute structure	Refined as an inversion twin	Flack x determined using 1011 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 ).
Absolute structure parameter	0.008 (13)	0.14 (3)
Computer programs: APEX3 and SAINT (Bruker, 2007 ), SHELXT2016/6 (Sheldrick, 2015a ), SHELXL2016/6 (Sheldrick, 2015b ), ORTEP-3 for Windows (Farrugia, 2012 ) and PLATON (Spek, 2009 ).

Supporting information

CCDC references: 1940144; 1940145

Crystal structure: contains datablocks I, II, global. DOI: https://doi.org/10.1107/S2056989019010004/wm5507sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989019010004/wm5507Isup2.hkl

Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S2056989019010004/wm5507IIsup3.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989019010004/wm5507Isup4.cml

Supporting information file. DOI: https://doi.org/10.1107/S2056989019010004/wm5507IIsup5.cml

checkCIF report

Computing details top

For both structures, data collection: APEX3 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXT2016/6 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016/6 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).

(E)-1-(4-Bromophenyl)-2-[2,2-dichloro-1-(4-nitrophenyl)ethenyl]diazene (I) top

Crystal data top

C₁₄H₈BrCl₂N₃O₂	D_x = 1.694 Mg m⁻³
M_r = 401.04	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna2₁	Cell parameters from 8656 reflections
a = 13.9181 (7) Å	θ = 2.9–27.0°
b = 13.4336 (6) Å	µ = 2.96 mm⁻¹
c = 8.4080 (4) Å	T = 296 K
V = 1572.05 (13) Å³	Plate, orange
Z = 4	0.19 × 0.14 × 0.08 mm
F(000) = 792

Data collection top

Bruker APEXII CCD diffractometer	2811 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.057
Absorption correction: multi-scan (SADABS; Bruker, 2003)	θ_max = 27.1°, θ_min = 2.9°
T_min = 0.608, T_max = 0.784	h = −17→17
23012 measured reflections	k = −14→17
3429 independent reflections	l = −10→10

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.033	w = 1/[σ²(F_o²) + (0.0253P)² + 0.7719P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.081	(Δ/σ)_max < 0.001
S = 1.02	Δρ_max = 0.31 e Å⁻³
3429 reflections	Δρ_min = −0.50 e Å⁻³
200 parameters	Absolute structure: Refined as an inversion twin
1 restraint	Absolute structure parameter: 0.008 (13)

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component inversion twin.

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

	x	y	z	U_iso*/U_eq
C1	0.4004 (2)	0.5082 (3)	0.5333 (5)	0.0393 (8)
C2	0.3711 (3)	0.4164 (3)	0.4764 (6)	0.0478 (10)
H2	0.309463	0.408665	0.435584	0.057*
C3	0.4334 (3)	0.3360 (3)	0.4803 (6)	0.0545 (11)
H3	0.414420	0.274430	0.440786	0.065*
C4	0.5228 (3)	0.3483 (3)	0.5428 (6)	0.0481 (9)
C5	0.5526 (3)	0.4381 (4)	0.6048 (7)	0.0582 (13)
H5	0.613115	0.444124	0.650896	0.070*
C6	0.4915 (3)	0.5191 (3)	0.5976 (6)	0.0539 (12)
H6	0.511337	0.580727	0.635893	0.065*
C7	0.1912 (2)	0.6569 (2)	0.5030 (5)	0.0378 (8)
C8	0.0975 (3)	0.6351 (3)	0.4948 (6)	0.0477 (10)
C9	0.2272 (3)	0.7616 (2)	0.5010 (5)	0.0345 (7)
C10	0.2658 (3)	0.8034 (3)	0.6372 (5)	0.0437 (9)
H10	0.270870	0.765504	0.729433	0.052*
C11	0.2966 (3)	0.9009 (3)	0.6369 (5)	0.0442 (9)
H11	0.321785	0.929565	0.728509	0.053*
C12	0.2896 (2)	0.9547 (3)	0.4988 (5)	0.0374 (8)
C13	0.2538 (4)	0.9149 (3)	0.3622 (5)	0.0511 (11)
H13	0.250600	0.952658	0.269651	0.061*
C14	0.2221 (3)	0.8170 (3)	0.3637 (5)	0.0491 (10)
H14	0.197279	0.788772	0.271406	0.059*
N1	0.3411 (2)	0.5954 (2)	0.5291 (5)	0.0427 (7)
N2	0.2537 (2)	0.5747 (2)	0.5107 (4)	0.0403 (7)
N3	0.3201 (2)	1.0595 (2)	0.4987 (5)	0.0483 (8)
O1	0.3418 (3)	1.0978 (3)	0.6245 (5)	0.0769 (11)
O2	0.3240 (4)	1.1036 (3)	0.3734 (5)	0.0863 (14)
Cl1	0.05489 (8)	0.51572 (8)	0.4988 (2)	0.0743 (4)
Cl2	0.00955 (8)	0.72322 (9)	0.4870 (2)	0.0713 (4)
Br1	0.60741 (4)	0.23804 (4)	0.54965 (11)	0.0809 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0435 (18)	0.0297 (16)	0.045 (2)	0.0001 (13)	0.0007 (18)	0.0047 (18)
C2	0.045 (2)	0.038 (2)	0.060 (3)	−0.0022 (16)	−0.0050 (19)	−0.007 (2)
C3	0.060 (3)	0.0298 (19)	0.074 (3)	−0.0012 (17)	−0.002 (2)	−0.006 (2)
C4	0.051 (2)	0.0365 (18)	0.057 (3)	0.0094 (15)	0.006 (2)	0.008 (2)
C5	0.043 (2)	0.046 (3)	0.085 (4)	0.0025 (18)	−0.010 (2)	0.002 (2)
C6	0.048 (2)	0.036 (2)	0.077 (3)	−0.0035 (16)	−0.011 (2)	−0.003 (2)
C7	0.0440 (18)	0.0276 (15)	0.042 (2)	0.0021 (14)	0.0025 (17)	0.0016 (16)
C8	0.046 (2)	0.0290 (18)	0.068 (3)	−0.0009 (14)	0.005 (2)	−0.0031 (18)
C9	0.0358 (17)	0.0277 (16)	0.0399 (19)	0.0020 (12)	0.0015 (15)	0.0014 (16)
C10	0.058 (3)	0.035 (2)	0.038 (2)	−0.0045 (18)	−0.0006 (18)	0.0050 (17)
C11	0.056 (2)	0.038 (2)	0.039 (2)	−0.0060 (18)	−0.0025 (18)	−0.0039 (17)
C12	0.0395 (17)	0.0273 (16)	0.045 (2)	0.0006 (13)	0.0045 (17)	0.0003 (17)
C13	0.069 (3)	0.039 (2)	0.046 (2)	−0.004 (2)	−0.006 (2)	0.0098 (18)
C14	0.065 (3)	0.041 (2)	0.041 (2)	−0.007 (2)	−0.009 (2)	0.0037 (18)
N1	0.0446 (16)	0.0288 (14)	0.055 (2)	−0.0015 (11)	0.0023 (16)	0.0018 (15)
N2	0.0437 (15)	0.0280 (13)	0.0493 (19)	0.0012 (12)	0.0009 (15)	0.0017 (14)
N3	0.0564 (19)	0.0302 (16)	0.058 (2)	−0.0046 (14)	0.0018 (19)	0.0012 (18)
O1	0.119 (3)	0.041 (2)	0.071 (2)	−0.022 (2)	−0.004 (2)	−0.0088 (18)
O2	0.142 (4)	0.044 (2)	0.074 (3)	−0.028 (2)	−0.011 (2)	0.0190 (19)
Cl1	0.0508 (6)	0.0360 (5)	0.1362 (12)	−0.0104 (4)	0.0112 (8)	−0.0047 (7)
Cl2	0.0438 (5)	0.0440 (6)	0.1260 (13)	0.0068 (4)	0.0004 (7)	−0.0025 (7)
Br1	0.0781 (3)	0.0554 (3)	0.1093 (5)	0.0306 (2)	0.0097 (4)	0.0087 (4)

Geometric parameters (Å, º) top

C1—C2	1.384 (5)	C8—Cl1	1.710 (4)
C1—C6	1.385 (6)	C9—C14	1.376 (6)
C1—N1	1.434 (4)	C9—C10	1.384 (6)
C2—C3	1.386 (6)	C10—C11	1.378 (6)
C2—H2	0.9300	C10—H10	0.9300
C3—C4	1.361 (6)	C11—C12	1.371 (6)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.377 (6)	C12—C13	1.361 (6)
C4—Br1	1.893 (4)	C12—N3	1.470 (4)
C5—C6	1.384 (6)	C13—C14	1.387 (6)
C5—H5	0.9300	C13—H13	0.9300
C6—H6	0.9300	C14—H14	0.9300
C7—C8	1.338 (5)	N1—N2	1.257 (4)
C7—N2	1.407 (4)	N3—O2	1.209 (5)
C7—C9	1.493 (4)	N3—O1	1.214 (5)
C8—Cl2	1.705 (4)

C2—C1—C6	120.0 (4)	C14—C9—C10	119.7 (3)
C2—C1—N1	123.3 (3)	C14—C9—C7	120.1 (3)
C6—C1—N1	116.7 (3)	C10—C9—C7	120.2 (3)
C1—C2—C3	120.1 (4)	C11—C10—C9	120.3 (4)
C1—C2—H2	120.0	C11—C10—H10	119.8
C3—C2—H2	120.0	C9—C10—H10	119.8
C4—C3—C2	119.1 (4)	C12—C11—C10	118.7 (4)
C4—C3—H3	120.4	C12—C11—H11	120.6
C2—C3—H3	120.4	C10—C11—H11	120.6
C3—C4—C5	121.9 (4)	C13—C12—C11	122.2 (3)
C3—C4—Br1	119.0 (3)	C13—C12—N3	118.8 (4)
C5—C4—Br1	119.1 (3)	C11—C12—N3	119.0 (4)
C4—C5—C6	119.1 (4)	C12—C13—C14	118.8 (4)
C4—C5—H5	120.4	C12—C13—H13	120.6
C6—C5—H5	120.4	C14—C13—H13	120.6
C5—C6—C1	119.8 (4)	C9—C14—C13	120.3 (4)
C5—C6—H6	120.1	C9—C14—H14	119.9
C1—C6—H6	120.1	C13—C14—H14	119.9
C8—C7—N2	115.7 (3)	N2—N1—C1	112.3 (3)
C8—C7—C9	122.2 (3)	N1—N2—C7	115.5 (3)
N2—C7—C9	122.2 (3)	O2—N3—O1	122.7 (3)
C7—C8—Cl2	123.3 (3)	O2—N3—C12	118.8 (4)
C7—C8—Cl1	122.8 (3)	O1—N3—C12	118.5 (4)
Cl2—C8—Cl1	113.8 (2)

C6—C1—C2—C3	−1.5 (7)	C7—C9—C10—C11	−178.3 (4)
N1—C1—C2—C3	178.2 (4)	C9—C10—C11—C12	−0.9 (7)
C1—C2—C3—C4	1.0 (7)	C10—C11—C12—C13	−0.4 (7)
C2—C3—C4—C5	1.1 (8)	C10—C11—C12—N3	178.4 (4)
C2—C3—C4—Br1	179.5 (4)	C11—C12—C13—C14	1.0 (7)
C3—C4—C5—C6	−2.7 (8)	N3—C12—C13—C14	−177.9 (4)
Br1—C4—C5—C6	179.0 (4)	C10—C9—C14—C13	−1.2 (7)
C4—C5—C6—C1	2.1 (8)	C7—C9—C14—C13	178.8 (4)
C2—C1—C6—C5	0.0 (7)	C12—C13—C14—C9	−0.1 (7)
N1—C1—C6—C5	−179.8 (4)	C2—C1—N1—N2	18.3 (6)
N2—C7—C8—Cl2	179.2 (3)	C6—C1—N1—N2	−161.9 (4)
C9—C7—C8—Cl2	−1.9 (7)	C1—N1—N2—C7	−179.1 (3)
N2—C7—C8—Cl1	1.8 (6)	C8—C7—N2—N1	−175.4 (4)
C9—C7—C8—Cl1	−179.4 (3)	C9—C7—N2—N1	5.7 (5)
C8—C7—C9—C14	−70.7 (6)	C13—C12—N3—O2	−9.3 (6)
N2—C7—C9—C14	108.1 (5)	C11—C12—N3—O2	171.8 (5)
C8—C7—C9—C10	109.3 (5)	C13—C12—N3—O1	171.9 (5)
N2—C7—C9—C10	−71.9 (5)	C11—C12—N3—O1	−7.0 (6)
C14—C9—C10—C11	1.7 (7)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C9–C14 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···Cl2ⁱ	0.93	2.92	3.593 (5)	131
C8—Cl2···Cg2ⁱⁱ	1.71 (1)	3.66 (1)	4.710 (5)	118 (1)

Symmetry codes: (i) x+1/2, −y+3/2, z; (ii) x−1/2, −y+3/2, z.

(E)-1-(4-Chlorophenyl)-2-[2,2-dichloro-1-(4-nitrophenyl)ethenyl]diazene (II) top

Crystal data top

C₁₄H₈Cl₃N₃O₂	D_x = 1.528 Mg m⁻³
M_r = 356.58	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna2₁	Cell parameters from 4206 reflections
a = 13.8689 (7) Å	θ = 2.9–26.4°
b = 13.3674 (7) Å	µ = 0.60 mm⁻¹
c = 8.3620 (5) Å	T = 296 K
V = 1550.24 (15) Å³	Prisme, orange
Z = 4	0.17 × 0.14 × 0.07 mm
F(000) = 720

Data collection top

Bruker APEXII CCD diffractometer	2547 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.038
Absorption correction: multi-scan (SADABS; Bruker, 2003)	θ_max = 26.4°, θ_min = 2.9°
T_min = 0.911, T_max = 0.946	h = −17→16
11687 measured reflections	k = −16→15
3156 independent reflections	l = −10→10

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.037	w = 1/[σ²(F_o²) + (0.0419P)² + 0.3296P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.091	(Δ/σ)_max < 0.001
S = 1.04	Δρ_max = 0.18 e Å⁻³
3156 reflections	Δρ_min = −0.25 e Å⁻³
199 parameters	Absolute structure: Flack x determined using 1011 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013).
1 restraint	Absolute structure parameter: 0.14 (3)

Special details top

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

	x	y	z	U_iso*/U_eq
C1	0.9044 (2)	0.0035 (2)	0.3115 (4)	0.0400 (8)
C2	0.8753 (3)	−0.0900 (2)	0.3650 (5)	0.0507 (9)
H2	0.813001	−0.099076	0.403349	0.061*
C3	0.9385 (3)	−0.1694 (2)	0.3615 (6)	0.0569 (10)
H3	0.919592	−0.231831	0.399107	0.068*
C4	1.0294 (3)	−0.1555 (3)	0.3023 (5)	0.0532 (10)
C5	1.0584 (3)	−0.0645 (3)	0.2434 (6)	0.0646 (12)
H5	1.119552	−0.056954	0.199546	0.077*
C6	0.9962 (3)	0.0155 (3)	0.2498 (6)	0.0607 (11)
H6	1.015836	0.077758	0.212526	0.073*
C7	0.6941 (2)	0.1515 (2)	0.3415 (4)	0.0376 (7)
C8	0.6001 (2)	0.1294 (2)	0.3491 (6)	0.0480 (8)
C9	0.7299 (2)	0.2569 (2)	0.3447 (5)	0.0364 (6)
C10	0.7644 (3)	0.3003 (3)	0.2053 (4)	0.0464 (9)
H10	0.766518	0.263150	0.111319	0.056*
C11	0.7955 (3)	0.3983 (3)	0.2056 (4)	0.0461 (9)
H11	0.818819	0.427923	0.112661	0.055*
C12	0.7913 (2)	0.4511 (2)	0.3468 (5)	0.0386 (7)
C13	0.7591 (3)	0.4093 (3)	0.4853 (5)	0.0530 (10)
H13	0.757981	0.446192	0.579602	0.064*
C14	0.7280 (3)	0.3110 (3)	0.4834 (5)	0.0507 (10)
H14	0.705639	0.281565	0.577118	0.061*
N1	0.8441 (2)	0.09023 (19)	0.3159 (4)	0.0446 (7)
N2	0.75630 (18)	0.06882 (17)	0.3339 (4)	0.0408 (6)
N3	0.8211 (2)	0.55693 (19)	0.3468 (5)	0.0487 (7)
O1	0.8400 (3)	0.5963 (2)	0.2197 (4)	0.0754 (10)
O2	0.8259 (3)	0.6004 (2)	0.4729 (4)	0.0879 (13)
Cl1	1.10869 (9)	−0.25630 (8)	0.2991 (2)	0.0857 (4)
Cl2	0.55690 (6)	0.00980 (6)	0.3445 (2)	0.0727 (3)
Cl3	0.51218 (7)	0.21874 (7)	0.3590 (2)	0.0751 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0437 (17)	0.0277 (14)	0.048 (2)	−0.0013 (12)	−0.0011 (15)	−0.0030 (14)
C2	0.0481 (18)	0.0381 (16)	0.066 (2)	−0.0012 (14)	0.008 (2)	0.008 (2)
C3	0.062 (2)	0.0325 (16)	0.076 (3)	−0.0010 (15)	0.003 (2)	0.007 (2)
C4	0.053 (2)	0.0379 (18)	0.069 (3)	0.0094 (15)	−0.0048 (18)	−0.0087 (18)
C5	0.046 (2)	0.054 (2)	0.093 (3)	0.0019 (18)	0.012 (2)	0.001 (2)
C6	0.052 (2)	0.039 (2)	0.091 (3)	−0.0075 (17)	0.008 (2)	0.004 (2)
C7	0.0461 (16)	0.0271 (13)	0.0397 (17)	0.0000 (12)	−0.0005 (18)	−0.0028 (17)
C8	0.0471 (17)	0.0284 (14)	0.069 (2)	−0.0008 (13)	−0.004 (2)	0.0006 (19)
C9	0.0361 (14)	0.0294 (13)	0.0437 (17)	0.0023 (11)	−0.0006 (16)	−0.0014 (19)
C10	0.065 (2)	0.037 (2)	0.037 (2)	−0.0058 (17)	0.0002 (18)	−0.0045 (16)
C11	0.061 (2)	0.038 (2)	0.039 (2)	−0.0090 (17)	0.0010 (17)	0.0031 (16)
C12	0.0427 (16)	0.0273 (13)	0.0458 (18)	−0.0003 (12)	−0.0036 (19)	−0.0010 (19)
C13	0.075 (3)	0.039 (2)	0.046 (2)	−0.0076 (19)	0.0109 (19)	−0.0099 (17)
C14	0.073 (3)	0.037 (2)	0.042 (2)	−0.0102 (18)	0.0089 (19)	−0.0038 (17)
N1	0.0476 (15)	0.0295 (12)	0.057 (2)	−0.0009 (11)	0.0003 (14)	−0.0009 (14)
N2	0.0427 (14)	0.0313 (12)	0.0485 (16)	−0.0006 (10)	−0.0025 (15)	−0.0011 (15)
N3	0.0533 (16)	0.0323 (13)	0.061 (2)	−0.0051 (12)	0.001 (2)	0.002 (2)
O1	0.118 (3)	0.0418 (17)	0.067 (2)	−0.0227 (18)	0.0012 (19)	0.0106 (17)
O2	0.149 (4)	0.0453 (19)	0.069 (2)	−0.028 (2)	0.013 (2)	−0.0211 (18)
Cl1	0.0767 (7)	0.0574 (6)	0.1230 (12)	0.0296 (5)	−0.0039 (7)	−0.0084 (7)
Cl2	0.0513 (5)	0.0375 (4)	0.1292 (10)	−0.0109 (3)	−0.0096 (7)	0.0036 (7)
Cl3	0.0456 (5)	0.0450 (5)	0.1348 (11)	0.0067 (4)	−0.0006 (7)	0.0016 (7)

Geometric parameters (Å, º) top

C1—C6	1.383 (5)	C8—Cl3	1.708 (3)
C1—C2	1.387 (5)	C9—C14	1.368 (5)
C1—N1	1.430 (4)	C9—C10	1.387 (5)
C2—C3	1.377 (5)	C10—C11	1.379 (5)
C2—H2	0.9300	C10—H10	0.9300
C3—C4	1.366 (6)	C11—C12	1.377 (5)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.373 (6)	C12—C13	1.362 (6)
C4—Cl1	1.740 (4)	C12—N3	1.473 (4)
C5—C6	1.374 (6)	C13—C14	1.382 (5)
C5—H5	0.9300	C13—H13	0.9300
C6—H6	0.9300	C14—H14	0.9300
C7—C8	1.339 (4)	N1—N2	1.259 (4)
C7—N2	1.404 (4)	N3—O2	1.207 (5)
C7—C9	1.493 (4)	N3—O1	1.214 (4)
C8—Cl2	1.708 (3)

C6—C1—C2	119.5 (3)	C14—C9—C10	119.9 (3)
C6—C1—N1	117.0 (3)	C14—C9—C7	120.5 (3)
C2—C1—N1	123.5 (3)	C10—C9—C7	119.6 (3)
C3—C2—C1	120.2 (3)	C11—C10—C9	120.3 (3)
C3—C2—H2	119.9	C11—C10—H10	119.9
C1—C2—H2	119.9	C9—C10—H10	119.9
C4—C3—C2	119.4 (3)	C12—C11—C10	118.4 (3)
C4—C3—H3	120.3	C12—C11—H11	120.8
C2—C3—H3	120.3	C10—C11—H11	120.8
C3—C4—C5	121.3 (3)	C13—C12—C11	122.2 (3)
C3—C4—Cl1	118.9 (3)	C13—C12—N3	119.1 (3)
C5—C4—Cl1	119.7 (3)	C11—C12—N3	118.7 (3)
C4—C5—C6	119.4 (4)	C12—C13—C14	118.9 (3)
C4—C5—H5	120.3	C12—C13—H13	120.6
C6—C5—H5	120.3	C14—C13—H13	120.6
C5—C6—C1	120.2 (4)	C9—C14—C13	120.4 (4)
C5—C6—H6	119.9	C9—C14—H14	119.8
C1—C6—H6	119.9	C13—C14—H14	119.8
C8—C7—N2	115.3 (3)	N2—N1—C1	112.6 (2)
C8—C7—C9	122.1 (3)	N1—N2—C7	114.9 (2)
N2—C7—C9	122.7 (3)	O2—N3—O1	123.0 (3)
C7—C8—Cl2	123.2 (2)	O2—N3—C12	118.5 (3)
C7—C8—Cl3	122.9 (2)	O1—N3—C12	118.4 (3)
Cl2—C8—Cl3	113.90 (19)

C6—C1—C2—C3	2.1 (7)	C7—C9—C10—C11	178.5 (3)
N1—C1—C2—C3	−178.0 (4)	C9—C10—C11—C12	0.0 (6)
C1—C2—C3—C4	−1.1 (7)	C10—C11—C12—C13	1.1 (6)
C2—C3—C4—C5	−1.3 (7)	C10—C11—C12—N3	−177.8 (3)
C2—C3—C4—Cl1	179.8 (3)	C11—C12—C13—C14	−1.1 (6)
C3—C4—C5—C6	2.6 (8)	N3—C12—C13—C14	177.7 (3)
Cl1—C4—C5—C6	−178.5 (4)	C10—C9—C14—C13	0.9 (6)
C4—C5—C6—C1	−1.6 (8)	C7—C9—C14—C13	−178.5 (4)
C2—C1—C6—C5	−0.8 (7)	C12—C13—C14—C9	0.1 (6)
N1—C1—C6—C5	179.4 (4)	C6—C1—N1—N2	162.9 (4)
N2—C7—C8—Cl2	−1.8 (6)	C2—C1—N1—N2	−17.0 (5)
C9—C7—C8—Cl2	179.6 (3)	C1—N1—N2—C7	179.0 (3)
N2—C7—C8—Cl3	−179.9 (3)	C8—C7—N2—N1	175.4 (4)
C9—C7—C8—Cl3	1.4 (6)	C9—C7—N2—N1	−5.9 (5)
C8—C7—C9—C14	73.1 (5)	C13—C12—N3—O2	7.8 (5)
N2—C7—C9—C14	−105.4 (4)	C11—C12—N3—O2	−173.3 (4)
C8—C7—C9—C10	−106.3 (5)	C13—C12—N3—O1	−172.4 (4)
N2—C7—C9—C10	75.2 (5)	C11—C12—N3—O1	6.5 (5)
C14—C9—C10—C11	−0.9 (6)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C9–C14 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C8—Cl3···Cg2ⁱ	1.71 (1)	3.62 (1)	4.703 (3)	120 (1)

Symmetry code: (i) x−1/2, −y+1/2, z.

Summary of short interatomic contacts (Å) in the crystal structures of compounds (I) and (II) top

Contact	Distance	Symmetry operation
	compound (I)
H10···Br1	3.18	1 - x, 1 - y, 1/2 + z
Br1···Cl1	3.5125 (12)	1/2 + x, 1/2 - y, z
H2···H11	2.54	1/2 - x, -1/2 + y, -1/2 + z
Cl2···H6	2.92	-1/2 + x, 3/2 - y, z
O2···H3	2.68	x, 1 + y, z
H13···N2	2.73	1/2 - x, 1/2 + y, -1/2 + z
	compound (II)
H10···Cl1	3.13	2 - x, -y, -1/2 + z
Cl1···Cl2	3.4847 (14)	1/2 + x, -1/2 - y, z
H2···H11	2.56	3/2 - x, -1/2 + y, 1/2 + z
Cl3···H6	2.98	-1/2 + x, 1/2 - y, z
O2···H3	2.66	x, 1 + y, z
H13···N2	2.69	3/2 - x, 1/2 + y, 1/2 + z

Percentage contributions of interatomic contacts to the Hirshfeld surface in the crystal structures of compounds (I) and (II) top

Contact	(I)	(II)
C···H/H···C	16.1	15.3
O···H/H···O	13.1	13.4
Cl···H/H···Cl	12.7	21.9
H···H	11.4	11.5
Br···H/H···Br	8.9	–
N···H/H···N	6.9	7.0
Cl···C/C···Cl	6.6	8.3
Cl···Br/Br···Cl	5.2	–
Cl···O/O···Cl	4.9	5.8
O···C/C···O	3.8	3.9
Cl···N/N···Cl	3.4	3.4
C···C	2.1	2.3
Br···C/C···Br	1.5	–
Br···O/O···Br	1.2	–
N···O/O···N	1.1	1.0
Cl···Cl	1.0	5.9
N···C/C···N	0.1	0.2
Br···N/N···Br	0.1	–

Acknowledgements

Funding for this research was provided by: Science Development Foundation under the President of the Republic of Azerbaijan (grant No. No EİF/ MQM/ Elm-Tehsil-1-2016-1(26)-71/06/4).

Funding information

Funding for this research was provided by: Science Development Foundation under the President of the Republic of Azerbaijan (grant No. No EİF/MQM/Elm-Tehsil-1-2016-1(26)-71/06/4).

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Volume 75| Part 8| August 2019| Pages 1199-1204

https://doi.org/10.1107/S2056989019010004

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

Crystal structures and Hirshfeld surface analyses of the two isotypic compounds (E)-1-(4-bromo­phen­yl)-2-[2,2-di­chloro-1-(4-nitro­phen­yl)ethen­yl]diazene and (E)-1-(4-chloro­phen­yl)-2-[2,2-di­chloro-1-(4-nitro­phen­yl)ethen­yl]diazene

1. Chemical context

2. Structural commentary

3. Supra­molecular features and Hirshfeld surface analysis

4. Database survey

5. Synthesis and crystallization

6. Refinement

Supporting information

Acknowledgements

Funding information

References

research communications

Crystal structures and Hirshfeld surface analyses of the two isotypic compounds (E)-1-(4-bromophenyl)-2-[2,2-dichloro-1-(4-nitrophenyl)ethenyl]diazene and (E)-1-(4-chlorophenyl)-2-[2,2-dichloro-1-(4-nitrophenyl)ethenyl]diazene

3. Supramolecular features and Hirshfeld surface analysis