Isotypic crystal structures of 2,6-di­bromo-N,N-bis­(4-nitro­phen­yl)aniline and 2,6-di­chloro-N,N-bis­(4-nitro­phen­yl)aniline

Kautny, P.; Fröhlich, J.; Stöger, B.; Weil, M.

doi:10.1107/S1600536814010964

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ISSN: 2056-9890

Volume 70| Part 8| August 2014| Pages 65-67

doi:10.1107/S1600536814010964

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Isotypic crystal structures of 2,6-dibromo-N,N-bis(4-nitrophenyl)aniline and 2,6-dichloro-N,N-bis(4-nitrophenyl)aniline

Paul Kautny,^a Johannes Fröhlich,^a Berthold Stöger ^b and Matthias Weil ^b ^*

^aInstitute of Applied Synthetic Chemistry, Vienna University of Technology, Getreidemarkt 9/163, A-1060 Vienna, Austria, and ^bInstitute for Chemical Technologies and Analytics, Division of Structural Chemistry, Vienna University of Technology, Getreidemarkt 9/164-SC, A-1060 Vienna, Austria
^*Correspondence e-mail: mweil@mail.zserv.tuwien.ac.at

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 13 February 2014; accepted 13 May 2014; online 19 July 2014)

In the molecules of the two isotypic title compounds, C₁₈H₁₁Br₂N₃O₄ (I) and C₁₈H₁₁Cl₂N₃O₄ (II), the triphenylamine N atoms show no sign of pyramidalization, with marginal displacements of the N atoms from the mean plane of the three connecting C atoms: 0.0058 (13) Å for the Br compound (I) and 0.0074 (9) Å for the Cl compound (II). In the crystals, molecules are linked through C—H⋯O hydrogen bonds between phenyl rings and nitro groups and by X⋯O (X = Br, Cl) interactions, that are shorter than the sum of the van der Waals radii, leading to a three-dimensional network.

Keywords: crystal structure; arylamines; isotypism.

CCDC references: 1004285; 1004286

1. Chemical context

Arylamines are among the most important electron donors for functional organic materials, e.g. organic light emitting diodes (OLEDs) (Shirota & Kageyama, 2007 ; Tao et al., 2011 ; Yook & Lee, 2012 ). In particular, triphenylamine-based compounds have received great attention due to their good hole-transport properties. Substituted triphenylamines are therefore highly desirable for further chemical modification, for example, cross-coupling or C—H activation.

We have investigated the conversion of 2,6-dihalogenated anilines (X = Cl, Br) with 1-fluoro-4-nitrobenzene. Despite the sterical demand of the halogen substituents, no diphenylamine intermediates were obtained whereas the title tetra-substituted triphenylamines (I) and (II) could be isolated and their crystal structures are reported here.

2. Structural commentary

Representative for both structures, the molecular structure of compound (II) is displayed in Fig. 1. The isotypic relation of both structures is reflected in the nearly identical bond lengths and angles in the molecules of (I) and (II), and as expected, only the C—X distances (X = Br, Cl) differ significantly. The N atoms in both structures show no pyramidalization, with only marginal displacements from the planes of the bonded C atoms (C1/C7/C13) of 0.0058 (13) Å for (I) and of 0.0074 (9) Å for (II).

Figure 1
The molecular structure of compound (II)

, with atom labelling. Displacement ellipsoids are drawn at the 70% probability level.

The dihedral angles between the benzene rings are 88.98 (7) (C1–C6)/(C13–C18), 82.07 (7) (C1–C6)/(C7–C12) and 51.97 (6)° (C7–C12)/(C13–C18) for (I). The corresponding values for (II) are 89.34 (4), 81.76 (5) and 49.41 (4)°.

The nitro groups are twisted slightly out of the plane of the benzene ring to which they are attached with dihedral angles of 8.29 (19) [(N3/O3/O4) / (C13–C18)] and 4.60 (19)° [(N2/O1/O2) / (C7–C11)] for (I). The corresponding values for (II) are 5.85 (13) and 4.81 (12)°.

3. Supramolecular features

The crystal packing of the structures of both (I) and (II) is consolidated by weak —C—H⋯O—N interactions (Tables 1 and 2) and X⋯O contacts that are shorter than the sum of the van der Waals radii (Bondi, 1964 ) of the respective elements. For (I) the Br⋯O contact is 3.3557 (13) Å, and for (II) the Cl⋯O contact is 3.2727 (9) Å. Both types of intermolecular interactions lead to the formation of a three-dimensional network (Fig. 2).

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H1C5⋯O3ⁱ	0.96	2.37	3.175 (2)	141
C12—H1C12⋯O2ⁱⁱ	0.96	2.49	3.347 (2)	148
Symmetry codes: (i) x, y, z+1; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H1C5⋯O3ⁱ	0.96	2.35	3.1950 (15)	147
C12—H1C12⋯O2ⁱⁱ	0.96	2.48	3.3304 (15)	148
Symmetry codes: (i) x, y, z+1; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Figure 2
A view of the crystal packing of compound (I)

, sustained by Br⋯O van der Waals contacts [dashed lines; weak C—H⋯O interactions are also present but are not shown for clarity; colour code: O red, C grey, Br ochre, H white]. The displacement ellipsoids are drawn at the 70% probability level.

4. Database survey

A search of the Cambridge Structural Database (Version 5.35, last update February 2014; Allen, 2002 ) indicated the presence of 759 molecules containing a triphenylamine backbone or of their metal-organic derivatives; they exclude, however, ring-closed systems such as N-phenylcarbazoles or N-phenylphenothiazines. None of these 759 molecules possesses the substitution pattern of the title compounds, viz. two para- and one ortho,ortho-substituted benzenes with respect to the N atom. The crystal structures of one para-nitro-substituted triphenylamine, viz. tris-(4-nitrophenyl)amine (Welch et al., 2005 ) and one ortho,ortho-dichloro-substituted triphenylamine, viz. tris-(2,3,4,5,6-pentachlorophenyl)amine (Hayes et al., 1980 ) have been reported. As in the title compounds, in both of these molecules the N atom is virtually coplanar with the three connecting C atoms. In the crystal structure of unsubstituted triphenylamine (Sobolev et al., 1985 ), on the other hand, in three out of four molecules, the N atom is located distinctly out of the plane defined by the connecting C atoms.

5. Synthesis and crystallization

Compound (I) was prepared by heating 2,6-dichloroaniline (405 mg, 2.50 mmol, 1.0 eq.), 1-fluoro-4-nitrobenzene (353 mg, 2.50 mmol, 1.0 eq.) and Cs₂CO₃ (896 mg, 2.75 mmol, 1.1 eq.) in DMSO (5 ml) at 413 K for 26 h in a capped vial using a heating block. After cooling, the reaction mixture was poured into water and the aqueous phase was extracted with CH₂Cl₂. The combined organic phases were dried over anhydrous Na₂SO₄ and concentrated under reduced pressure. Compound (I) was obtained after column chromatography (light petroleum:EtOAc 7:3) as a yellow solid (374 mg, 0.93 mmol, 74%). Yellow single crystals were grown from a CDCl₃ solution by slow evaporation of the solvent. Spectroscopic data for compound (I) are available in the archived CIF.

Compound (II) was prepared by heating 2,6-dibromoaniline (627 mg, 2.50 mmol, 1.0 eq.), 1-fluoro-4-nitrobenzene (353 mg, 2.50 mmol, 1.0 eq.) and Cs₂CO₃ (896 mg, 2.75 mmol, 1.1 eq.) in DMSO (5 ml) at 413 K for 18 h in a capped vial using a heating block. After cooling, the reaction mixture was poured into water and the aqueous phase was extracted with CH₂Cl₂. The combined organic phases were dried over anhydrous Na₂SO₄ and concentrated under reduced pressure. Compound (II) was obtained after crystallization from an EtOH/toluene mixture as a brown solid (237 mg, 0.48 mmol, 38%). Yellow single crystals were grown from a CDCl₃ solution by slow evaporation of the solvent. Spectroscopic data for compound (II) are available in the archived CIF.

6. Refinement

The hydrogen atoms in both structures, (I) and (II), were clearly discernible from difference Fourier maps and were refined as riding with C—H = 0.96 Å and U_iso(H) = 1.2U_eq(C). Experimental details are given in Table 3.

Table 3
Experimental details

	(I)	(II)
Crystal data
Chemical formula	C₁₈H₁₁Br₂N₃O₄	C₁₈H₁₁Cl₂N₃O₄
M_r	493.1	404.2
Crystal system, space group	Monoclinic, P2₁/c	Monoclinic, P2₁/c
Temperature (K)	100	100
a, b, c (Å)	13.4705 (7), 11.6686 (6), 11.7081 (7)	13.3117 (3), 11.5460 (3), 11.7558 (3)
β (°)	107.576 (2)	108.7971 (10)
V (Å³)	1754.39 (17)	1710.46 (7)
Z	4	4
Radiation type	Mo Kα	Mo Kα
μ (mm⁻¹)	4.65	0.41
Crystal size (mm)	0.80 × 0.56 × 0.20	0.76 × 0.65 × 0.35

Data collection
Diffractometer	Bruker KAPPA APEXII CCD	Bruker KAPPA APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2013 )	Multi-scan (SADABS; Bruker, 2013)
T_min, T_max	0.055, 0.390	0.74, 0.87
No. of measured, independent and observed [I > 3σ(I)] reflections	52187, 7731, 5557	29061, 4959, 4374
R_int	0.045	0.031
(sin θ/λ)_max (Å⁻¹)	0.808	0.704

Refinement
R[F² > 3σ(F²)], wR(F²), S	0.034, 0.079, 1.36	0.034, 0.131, 1.39
No. of reflections	7731	4959
No. of parameters	244	244
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.00, −0.91	0.24, −0.23
Computer programs: APEX2 and SAINT-Plus (Bruker, 2013), SUPERFLIP (Palatinus & Chapuis, 2007 ), JANA2006 (Petříček et al., 2014 ), Mercury (Macrae et al., 2008 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC references: 1004285; 1004286

Crystal structure: contains datablocks general, I, II. DOI: 10.1107/S1600536814010964/su0003sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814010964/su0003Isup2.hkl

Structure factors: contains datablock II. DOI: 10.1107/S1600536814010964/su0003IIsup3.hkl

Supporting information file. DOI: 10.1107/S1600536814010964/su0003Isup4.cml

Supporting information file. DOI: 10.1107/S1600536814010964/su0003IIsup5.cml

checkCIF report

Chemical context top

Arylamines are among the most important electron donors for functional organic materials, e.g. organic light emitting diodes (OLEDs) (Shirota & Kageyama, 2007; Tao et al., 2011; Yook & Lee, 2012). In particular, triphenylamine-based compounds have received great attention due to their good hole-transport properties. Substituted triphenylamines are therefore highly desirable for further chemical modification, for example, cross-coupling or C—H activation.

Structural commentary top

Representative for both structures, the molecular structure of compound (II) is displayed in Fig. 1. The isotypic relation of both structures is reflected in the nearly identical bond distances and angles in the molecules of (I) and (II), and as expected, only the C—X distances (X = Br, Cl) differ significantly. The N atoms in both structures show no pyramidalization, with only marginal displacements from the planes of the bonded C atoms (C1/C7/C13) of 0.0058 (13) Å for (I) and of 0.0074 (9) Å for (II).

Supramolecular features top

The crystal packing of the structures of both (I) and (II) is consolidated by weak —C—H···O—N interactions (Table 1) and X···O contacts that are shorter than the sum of the van der Waals radii (Bondi, 1964) of the respective elements. For (I) the Br···O contact is 3.3557 (13) Å, and for (II) the Cl···O contact is 3.2727 (9) Å. Both types of intermolecular interactions lead to the formation of a three-dimensional network (Fig. 2).

Database survey top

A search of the Cambridge Structural Database (CSD, V5.35, last update Nov. 2013; Allen, 2002) indicated the presence of 759 molecules containing a triphenylamine backbone or of their metal-organic derivatives; they exclude, however, ring-closed systems such as N-phenylcarbazoles or N-phenylphenothiazines. None of these 759 molecules possesses the substitution pattern of the title compounds, viz. two para- and one ortho,ortho-substituted benzenes with respect to the N atom. The crystal structures of one para-nitro-substituted triphenylamine, viz. tris-(4-nitrophenyl)amine (Welch et al., 2005) and one ortho,ortho-dichloro-substituted triphenylamine, viz. tris-(2,3,4,5,6-pentachlorophenyl)amine (Hayes et al., 1980) have been reported. As in the title compounds, in both of these molecules the N atom is virtually coplanar with the three connecting C atoms. In the crystal structure of unsubstituted triphenylamine (Sobolev et al., 1985), on the other hand, in three out of four molecules, the N atom is located distinctly out of the plane defined by the connecting C atoms.

Synthesis and crystallization top

Compound (I) was prepared by heating 2,6-dichloroaniline (405 mg, 2.50 mmol, 1.0 eq.), 1-fluoro-4-nitrobenzene (353 mg, 2.50 mmol, 1.0 eq.) and Cs₂CO₃ (896 mg, 2.75 mmol, 1.1 eq.) in DMSO (5 ml) at 413 K for 26 h in a capped vial using a heating block. After cooling, the reaction mixture was poured into water and the aqueous phase was extracted with CH₂Cl₂. The combined organic phases were dried over anhydrous Na₂SO₄ and concentrated under reduced pressure. Compound (I) was obtained after column chromatography (light petroleum:EtOAc 7:3) as a yellow solid (374 mg, 0.93 mmol, 74 %). Yellow single crystals were grown from a CDCl₃ solution by slow evaporation of the solvent. Spectroscopic data for compound (I) are available in the archived CIF.

Compound (II) was prepared by heating 2,6-dibromoaniline (627 mg, 2.50 mmol, 1.0 eq.), 1-fluoro-4-nitrobenzene (353 mg, 2.50 mmol, 1.0 eq.) and Cs₂CO₃ (896 mg, 2.75 mmol, 1.1 eq.) in DMSO (5 ml) at 413 K for 18 h in a capped vial using a heating block. After cooling, the reaction mixture was poured into water and the aqueous phase was extracted with CH₂Cl₂. The combined organic phases were dried over anhydrous Na₂SO₄ and concentrated under reduced pressure. Compound (II) was obtained after crystallization from an EtOH/toluene mixture as a brown solid (237 mg, 0.48 mmol, 38 %). Yellow single crystals were grown from a CDCl₃ solution by slow evaporation of the solvent. Spectroscopic data for compound (II) are available in the archived CIF.

Refinement top

The hydrogen atoms in both structures, (I) and (II), were clearly discernible from difference Fourier maps and were refined as riding with C—H = 0.96 Å and U_iso(H) = 1.2U_eq(C) [OK?].

Related literature top

For related literature, see: Allen (2002); Bondi (1964); Hayes et al. (1980); Shirota & Kageyama (2007); Sobolev et al. (1985); Tao et al. (2011); Welch et al. (2005); Yook & Lee (2012).

Computing details top

For both compounds, data collection: APEX2 (Bruker, 2013); cell refinement: SAINT-Plus (Bruker, 2013); data reduction: SAINT-Plus (Bruker, 2013). Program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007) for (I); coordinates taken from Br analogue for (II). Program(s) used to refine structure: JANA2006 (Petříček, et al., 2006) for (I); JANA2006 (Petříček, et al., 2006) for (II). For both compounds, molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of compound (II), with atom labelling. Displacement ellipsoids are drawn at the 70% probability level.
	Fig. 2. A view of the crystal packing of compound (I), sustained by Br···O van der Waals contacts [dashed lines; weak C—H···O interactions are also present but are not shown for clarity; colour code: O red, C grey, Br ochre, H white]. The displacement ellipsoids are drawn at the 70% probability level.

(I) 2,6-Dibromo-N,N-bis(4-nitrophenyl)aniline top

Crystal data top

C₁₈H₁₁Br₂N₃O₄	F(000) = 968
M_r = 493.1	D_x = 1.866 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ycb	Cell parameters from 9998 reflections
a = 13.4705 (7) Å	θ = 2.9–34.9°
b = 11.6686 (6) Å	µ = 4.65 mm⁻¹
c = 11.7081 (7) Å	T = 100 K
β = 107.576 (2)°	Triangular prism, translucent yellow
V = 1754.39 (17) Å³	0.80 × 0.56 × 0.20 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	7731 independent reflections
Radiation source: X-ray tube	5557 reflections with I > 3σ(I)
Graphite monochromator	R_int = 0.045
ω and ϕ scans	θ_max = 35.1°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2013)	h = −21→21
T_min = 0.055, T_max = 0.390	k = −18→18
52187 measured reflections	l = −18→18

Refinement top

Refinement on F²	Primary atom site location: iterative
R[F² > 2σ(F²)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.079	H-atom parameters constrained
S = 1.36	Weighting scheme based on measured s.u.'s w = 1/(σ²(I) + 0.0009I²)
7731 reflections	(Δ/σ)_max = 0.007
244 parameters	Δρ_max = 1.00 e Å⁻³
0 restraints	Δρ_min = −0.91 e Å⁻³
44 constraints

Crystal data top

C₁₈H₁₁Br₂N₃O₄	V = 1754.39 (17) Å³
M_r = 493.1	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.4705 (7) Å	µ = 4.65 mm⁻¹
b = 11.6686 (6) Å	T = 100 K
c = 11.7081 (7) Å	0.80 × 0.56 × 0.20 mm
β = 107.576 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	7731 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2013)	5557 reflections with I > 3σ(I)
T_min = 0.055, T_max = 0.390	R_int = 0.045
52187 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.079	H-atom parameters constrained
S = 1.36	Δρ_max = 1.00 e Å⁻³
7731 reflections	Δρ_min = −0.91 e Å⁻³
244 parameters

Special details top

Experimental. Spectroscopic data for compound (I): ¹H NMR (200 MHz, CDCl₃): δ = 8.18 (d, J = 9.1 Hz, 4H), 7.56–7.49 (m, 2H), 7.40 (dd, J = 9.2, 6.6 Hz, 1H), 7.09 (d, J = 9.1 Hz, 4H) p.p.m.. ¹³C NMR (50 MHz, CDCl₃): δ = 149.3 (s), 143.0 (s), 138.0 (s), 136.4 (s), 130.6 (d), 130.1 (d), 125.6 (d), 120.4 (d) p.p.m..

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

	x	y	z	U_iso*/U_eq
Br1	0.573900 (13)	0.859367 (14)	0.064003 (15)	0.01908 (5)
Br2	0.901801 (14)	1.107097 (16)	0.387459 (16)	0.02362 (6)
O1	0.60098 (10)	1.55865 (11)	0.07605 (12)	0.0242 (4)
O2	0.52588 (11)	1.50312 (11)	0.20583 (12)	0.0258 (4)
O3	0.89116 (11)	0.84226 (12)	−0.27898 (11)	0.0275 (5)
O4	1.01356 (11)	0.77627 (12)	−0.12917 (12)	0.0279 (5)
N1	0.74647 (10)	1.04271 (11)	0.14278 (11)	0.0116 (4)
N2	0.57864 (11)	1.48465 (12)	0.13859 (12)	0.0169 (4)
N3	0.93586 (11)	0.83519 (12)	−0.17142 (12)	0.0166 (4)
C1	0.74189 (12)	0.96819 (13)	0.23780 (13)	0.0119 (4)
C2	0.67254 (13)	0.87583 (13)	0.21625 (15)	0.0146 (5)
C3	0.67200 (13)	0.79887 (15)	0.30661 (16)	0.0199 (5)
C4	0.73845 (14)	0.81727 (16)	0.42090 (16)	0.0225 (6)
C5	0.80581 (14)	0.90916 (15)	0.44579 (15)	0.0191 (5)
C6	0.80787 (13)	0.98333 (13)	0.35429 (14)	0.0150 (5)
C7	0.70196 (12)	1.15186 (12)	0.13580 (13)	0.0108 (4)
C8	0.72745 (13)	1.24028 (13)	0.06810 (14)	0.0143 (5)
C9	0.68543 (13)	1.34821 (13)	0.06712 (14)	0.0150 (5)
C10	0.61940 (12)	1.36934 (13)	0.13585 (14)	0.0132 (4)
C11	0.59367 (12)	1.28422 (13)	0.20434 (14)	0.0132 (4)
C12	0.63388 (12)	1.17542 (13)	0.20293 (13)	0.0128 (4)
C13	0.79772 (12)	0.99930 (12)	0.06341 (13)	0.0114 (4)
C14	0.75857 (13)	1.01765 (14)	−0.06029 (13)	0.0153 (5)
C15	0.80630 (13)	0.96656 (14)	−0.13642 (14)	0.0158 (5)
C16	0.89197 (12)	0.89691 (13)	−0.08923 (13)	0.0126 (4)
C17	0.93330 (12)	0.87926 (13)	0.03259 (14)	0.0138 (4)
C18	0.88567 (12)	0.93065 (13)	0.10882 (13)	0.0129 (4)
H1c3	0.62618	0.733863	0.289983	0.0239*
H1c4	0.737607	0.765079	0.483986	0.027*
H1c5	0.850818	0.921597	0.525706	0.023*
H1c8	0.774364	1.225481	0.02228	0.0171*
H1c9	0.701637	1.408126	0.019449	0.018*
H1c11	0.548604	1.300523	0.252057	0.0158*
H1c12	0.615028	1.115297	0.248386	0.0154*
H1c14	0.698685	1.065633	−0.092153	0.0183*
H1c15	0.780239	0.979303	−0.221267	0.0189*
H1c17	0.993928	0.83222	0.063785	0.0165*
H1c18	0.913367	0.918984	0.19371	0.0154*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.01575 (8)	0.01677 (8)	0.02273 (9)	−0.00120 (6)	0.00282 (6)	−0.00462 (6)
Br2	0.02243 (9)	0.02083 (9)	0.02160 (9)	−0.00396 (7)	−0.00238 (7)	−0.00316 (7)
O1	0.0279 (7)	0.0125 (6)	0.0333 (7)	0.0028 (5)	0.0109 (6)	0.0051 (5)
O2	0.0296 (7)	0.0224 (6)	0.0294 (7)	0.0104 (5)	0.0153 (6)	−0.0009 (5)
O3	0.0331 (8)	0.0390 (8)	0.0116 (6)	0.0113 (6)	0.0086 (5)	0.0004 (5)
O4	0.0290 (7)	0.0353 (8)	0.0214 (6)	0.0179 (6)	0.0106 (6)	0.0037 (5)
N1	0.0163 (6)	0.0096 (5)	0.0106 (6)	0.0021 (4)	0.0063 (5)	0.0016 (4)
N2	0.0158 (6)	0.0131 (6)	0.0193 (7)	0.0025 (5)	0.0016 (5)	−0.0010 (5)
N3	0.0186 (7)	0.0181 (7)	0.0150 (6)	0.0022 (5)	0.0081 (5)	0.0015 (5)
C1	0.0141 (7)	0.0111 (6)	0.0125 (7)	0.0027 (5)	0.0069 (5)	0.0024 (5)
C2	0.0125 (7)	0.0127 (7)	0.0194 (8)	0.0026 (5)	0.0060 (6)	0.0010 (5)
C3	0.0153 (8)	0.0157 (7)	0.0320 (9)	0.0045 (6)	0.0120 (7)	0.0099 (7)
C4	0.0206 (8)	0.0251 (9)	0.0264 (9)	0.0105 (7)	0.0140 (7)	0.0151 (7)
C5	0.0201 (8)	0.0260 (9)	0.0132 (7)	0.0088 (6)	0.0077 (6)	0.0065 (6)
C6	0.0162 (7)	0.0154 (7)	0.0144 (7)	0.0017 (6)	0.0063 (6)	0.0004 (6)
C7	0.0121 (6)	0.0105 (6)	0.0099 (6)	0.0004 (5)	0.0034 (5)	0.0009 (5)
C8	0.0163 (7)	0.0132 (7)	0.0155 (7)	0.0010 (5)	0.0082 (6)	0.0020 (5)
C9	0.0167 (7)	0.0131 (7)	0.0165 (7)	0.0005 (5)	0.0068 (6)	0.0026 (5)
C10	0.0118 (7)	0.0112 (6)	0.0155 (7)	0.0017 (5)	0.0025 (5)	−0.0026 (5)
C11	0.0113 (7)	0.0146 (7)	0.0137 (7)	0.0003 (5)	0.0038 (5)	−0.0013 (5)
C12	0.0130 (7)	0.0127 (6)	0.0136 (7)	−0.0005 (5)	0.0054 (5)	0.0007 (5)
C13	0.0135 (7)	0.0101 (6)	0.0109 (6)	0.0003 (5)	0.0043 (5)	0.0002 (5)
C14	0.0162 (7)	0.0167 (7)	0.0124 (7)	0.0050 (6)	0.0036 (6)	0.0025 (5)
C15	0.0196 (8)	0.0180 (7)	0.0099 (6)	0.0037 (6)	0.0047 (6)	0.0030 (5)
C16	0.0141 (7)	0.0133 (7)	0.0123 (7)	0.0005 (5)	0.0067 (5)	−0.0007 (5)
C17	0.0140 (7)	0.0133 (7)	0.0135 (7)	0.0022 (5)	0.0033 (5)	0.0014 (5)
C18	0.0147 (7)	0.0138 (7)	0.0096 (6)	0.0010 (5)	0.0029 (5)	0.0010 (5)

Geometric parameters (Å, º) top

Br1—N1	3.0882 (13)	C5—H1c5	0.96
Br1—C2	1.8840 (15)	C7—C8	1.405 (2)
Br2—N1	3.0869 (12)	C7—C12	1.403 (3)
Br2—C6	1.8817 (16)	C8—C9	1.379 (2)
O1—N2	1.227 (2)	C8—H1c8	0.96
O2—N2	1.228 (2)	C9—C10	1.390 (3)
O3—N3	1.2237 (17)	C9—H1c9	0.96
O4—N3	1.2247 (19)	C10—C11	1.385 (2)
N1—C1	1.428 (2)	C11—C12	1.382 (2)
N1—C7	1.3995 (19)	C11—H1c11	0.96
N1—C13	1.409 (2)	C12—H1c12	0.96
N2—C10	1.457 (2)	C13—C14	1.400 (2)
N3—C16	1.462 (2)	C13—C18	1.396 (2)
C1—C2	1.398 (2)	C14—C15	1.382 (3)
C1—C6	1.396 (2)	C14—H1c14	0.96
C2—C3	1.389 (3)	C15—C16	1.383 (2)
C3—C4	1.384 (2)	C15—H1c15	0.96
C3—H1c3	0.96	C16—C17	1.381 (2)
C4—C5	1.378 (3)	C17—C18	1.383 (3)
C4—H1c4	0.96	C17—H1c17	0.96
C5—C6	1.384 (2)	C18—H1c18	0.96

N1—Br1—C2	52.74 (6)	N1—C7—C8	121.85 (16)
N1—Br2—C6	52.88 (5)	N1—C7—C12	119.11 (14)
Br1—N1—Br2	133.15 (5)	C8—C7—C12	118.97 (14)
Br1—N1—C1	66.74 (7)	C7—C8—C9	120.36 (17)
Br1—N1—C7	110.03 (9)	C7—C8—H1c8	119.82
Br1—N1—C13	91.63 (8)	C9—C8—H1c8	119.82
Br2—N1—C1	66.54 (7)	C8—C9—C10	119.34 (16)
Br2—N1—C7	89.49 (8)	C8—C9—H1c9	120.33
Br2—N1—C13	111.71 (8)	C10—C9—H1c9	120.33
C1—N1—C7	118.76 (14)	N2—C10—C9	119.20 (15)
C1—N1—C13	116.10 (12)	N2—C10—C11	119.18 (16)
C7—N1—C13	125.13 (13)	C9—C10—C11	121.60 (15)
O1—N2—O2	123.55 (15)	C10—C11—C12	118.96 (16)
O1—N2—C10	118.34 (16)	C10—C11—H1c11	120.52
O2—N2—C10	118.09 (14)	C12—C11—H1c11	120.52
O3—N3—O4	123.27 (16)	C7—C12—C11	120.75 (15)
O3—N3—C16	118.22 (14)	C7—C12—H1c12	119.63
O4—N3—C16	118.47 (13)	C11—C12—H1c12	119.62
N1—C1—C2	120.82 (12)	N1—C13—C14	121.39 (13)
N1—C1—C6	121.30 (13)	N1—C13—C18	118.94 (13)
C2—C1—C6	117.86 (15)	C14—C13—C18	119.55 (16)
Br1—C2—C1	119.42 (12)	C13—C14—C15	119.86 (14)
Br1—C2—C3	119.35 (12)	C13—C14—H1c14	120.07
C1—C2—C3	121.17 (14)	C15—C14—H1c14	120.07
C2—C3—C4	119.04 (16)	C14—C15—C16	119.38 (14)
C2—C3—H1c3	120.48	C14—C15—H1c15	120.31
C4—C3—H1c3	120.48	C16—C15—H1c15	120.31
C3—C4—C5	121.18 (17)	N3—C16—C15	118.75 (13)
C3—C4—H1c4	119.41	N3—C16—C17	119.29 (14)
C5—C4—H1c4	119.41	C15—C16—C17	121.85 (16)
C4—C5—C6	119.27 (14)	C16—C17—C18	118.74 (14)
C4—C5—H1c5	120.37	C16—C17—H1c17	120.63
C6—C5—H1c5	120.37	C18—C17—H1c17	120.63
Br2—C6—C1	119.26 (12)	C13—C18—C17	120.58 (14)
Br2—C6—C5	119.31 (11)	C13—C18—H1c18	119.71
C1—C6—C5	121.42 (15)	C17—C18—H1c18	119.71

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H1C5···O3ⁱ	0.96	2.37	3.175 (2)	141
C12—H1C12···O2ⁱⁱ	0.96	2.49	3.347 (2)	148

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

(II) 2,6-Dichloro-N,N-bis(4-nitrophenyl)aniline top

Crystal data top

C₁₈H₁₁Cl₂N₃O₄	F(000) = 824
M_r = 404.2	D_x = 1.569 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ycb	Cell parameters from 9690 reflections
a = 13.3117 (3) Å	θ = 3.9–30.0°
b = 11.5460 (3) Å	µ = 0.41 mm⁻¹
c = 11.7558 (3) Å	T = 100 K
β = 108.7971 (10)°	Block, translucent yellow
V = 1710.46 (7) Å³	0.76 × 0.65 × 0.35 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	4959 independent reflections
Radiation source: X-ray tube	4374 reflections with I > 3σ(I)
Graphite monochromator	R_int = 0.031
ω and ϕ scans	θ_max = 30.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2013)	h = −18→18
T_min = 0.74, T_max = 0.87	k = −16→15
29061 measured reflections	l = −16→16

Refinement top

Refinement on F²	Primary atom site location: isomorphous structure methods
R[F² > 2σ(F²)] = 0.034	Hydrogen site location: isomorphous structure methods
wR(F²) = 0.131	H-atom parameters constrained
S = 1.39	Weighting scheme based on measured s.u.'s w = 1/(σ²(I) + 0.0064I²)
4959 reflections	(Δ/σ)_max = 0.018
244 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³
44 constraints

Crystal data top

C₁₈H₁₁Cl₂N₃O₄	V = 1710.46 (7) Å³
M_r = 404.2	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.3117 (3) Å	µ = 0.41 mm⁻¹
b = 11.5460 (3) Å	T = 100 K
c = 11.7558 (3) Å	0.76 × 0.65 × 0.35 mm
β = 108.7971 (10)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	4959 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2013)	4374 reflections with I > 3σ(I)
T_min = 0.74, T_max = 0.87	R_int = 0.031
29061 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.131	H-atom parameters constrained
S = 1.39	Δρ_max = 0.24 e Å⁻³
4959 reflections	Δρ_min = −0.23 e Å⁻³
244 parameters

Special details top

Experimental. Spectroscopic data for compound (II): ¹H NMR (200 MHz, CDCl₃): δ = 8.19 (d, J =9.2 Hz, 4H), 7.74 (d, J = 8.1 Hz, 2H), 7.25 (t, J = 8.1 Hz, 1H), 7.10 (d, J = 9.2 Hz, 4H) p.p.m.. ¹³C NMR (50 MHz, CDCl₃): δ = 144.9 (s), 142.9 (s), 140.6 (s), 134.1 (d), 131.5 (d), 126.5 (s), 125.5 (d), 120.5 (d) p.p.m..

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

	x	y	z	U_iso*/U_eq
Cl1	0.58310 (2)	0.86376 (2)	0.06717 (3)	0.02676 (11)
Cl2	0.89794 (2)	1.09658 (2)	0.39011 (3)	0.02968 (11)
O1	0.59995 (7)	1.56656 (7)	0.07725 (8)	0.0250 (3)
O2	0.52501 (8)	1.50838 (7)	0.20576 (9)	0.0278 (3)
O3	0.90032 (8)	0.85088 (9)	−0.27494 (8)	0.0324 (3)
O4	1.01290 (8)	0.76623 (8)	−0.12423 (8)	0.0288 (3)
N1	0.75055 (7)	1.04563 (7)	0.14397 (7)	0.0145 (3)
N2	0.57820 (7)	1.49072 (7)	0.13910 (8)	0.0183 (3)
N3	0.94009 (7)	0.83429 (8)	−0.16642 (8)	0.0174 (3)
C1	0.74413 (8)	0.96904 (8)	0.23650 (9)	0.0145 (3)
C2	0.67230 (9)	0.87665 (8)	0.21010 (10)	0.0185 (3)
C3	0.66959 (9)	0.79754 (9)	0.29820 (12)	0.0260 (4)
C4	0.73555 (11)	0.81422 (10)	0.41472 (12)	0.0297 (4)
C5	0.80543 (10)	0.90616 (10)	0.44433 (11)	0.0253 (4)
C6	0.80964 (9)	0.98244 (9)	0.35460 (10)	0.0184 (3)
C7	0.70496 (8)	1.15578 (8)	0.13637 (9)	0.0133 (3)
C8	0.73029 (9)	1.24530 (8)	0.06960 (9)	0.0166 (3)
C9	0.68665 (9)	1.35445 (8)	0.06821 (10)	0.0172 (3)
C10	0.61973 (8)	1.37467 (8)	0.13544 (9)	0.0151 (3)
C11	0.59475 (8)	1.28778 (8)	0.20337 (9)	0.0158 (3)
C12	0.63582 (8)	1.17818 (8)	0.20218 (9)	0.0151 (3)
C13	0.80210 (8)	1.00128 (8)	0.06577 (9)	0.0137 (3)
C14	0.76400 (9)	1.02286 (8)	−0.05822 (9)	0.0179 (3)
C15	0.81196 (9)	0.97117 (8)	−0.13329 (9)	0.0174 (3)
C16	0.89655 (8)	0.89650 (8)	−0.08506 (9)	0.0141 (3)
C17	0.93636 (8)	0.87409 (8)	0.03712 (9)	0.0145 (3)
C18	0.88927 (8)	0.92743 (8)	0.11260 (9)	0.0146 (3)
H1c3	0.622526	0.732212	0.27836	0.0311*
H1c4	0.732728	0.760843	0.476226	0.0357*
H1c5	0.850452	0.917238	0.525723	0.0303*
H1c8	0.777925	1.230913	0.024835	0.02*
H1c9	0.702539	1.415466	0.021211	0.0206*
H1c11	0.549454	1.3037	0.250608	0.019*
H1c12	0.616983	1.116869	0.246644	0.0181*
H1c14	0.704527	1.073604	−0.090899	0.0215*
H1c15	0.786988	0.986778	−0.218011	0.0209*
H1c17	0.995418	0.822599	0.06882	0.0174*
H1c18	0.91652	0.913735	0.197601	0.0175*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.01996 (17)	0.02079 (16)	0.0347 (2)	−0.00131 (9)	0.00215 (13)	−0.00737 (10)
Cl2	0.02831 (18)	0.02495 (16)	0.02653 (18)	−0.00245 (10)	−0.00402 (13)	−0.00497 (10)
O1	0.0279 (4)	0.0138 (3)	0.0335 (5)	0.0024 (3)	0.0100 (4)	0.0026 (3)
O2	0.0302 (5)	0.0245 (4)	0.0330 (5)	0.0096 (3)	0.0163 (4)	−0.0016 (3)
O3	0.0390 (5)	0.0457 (5)	0.0141 (4)	0.0168 (4)	0.0108 (4)	0.0031 (3)
O4	0.0294 (5)	0.0346 (4)	0.0233 (4)	0.0162 (4)	0.0100 (4)	0.0014 (3)
N1	0.0186 (4)	0.0124 (3)	0.0139 (4)	0.0030 (3)	0.0073 (3)	0.0024 (3)
N2	0.0166 (4)	0.0150 (4)	0.0212 (4)	0.0035 (3)	0.0031 (3)	−0.0018 (3)
N3	0.0181 (4)	0.0198 (4)	0.0160 (4)	0.0011 (3)	0.0078 (3)	0.0000 (3)
C1	0.0167 (5)	0.0128 (4)	0.0158 (5)	0.0029 (3)	0.0076 (4)	0.0025 (3)
C2	0.0161 (5)	0.0135 (4)	0.0277 (6)	0.0025 (3)	0.0093 (4)	0.0016 (4)
C3	0.0205 (5)	0.0164 (4)	0.0473 (8)	0.0057 (4)	0.0198 (5)	0.0120 (4)
C4	0.0322 (6)	0.0284 (5)	0.0390 (7)	0.0167 (5)	0.0260 (6)	0.0208 (5)
C5	0.0297 (6)	0.0309 (5)	0.0179 (5)	0.0146 (5)	0.0114 (5)	0.0087 (4)
C6	0.0205 (5)	0.0195 (4)	0.0156 (5)	0.0042 (4)	0.0064 (4)	0.0005 (4)
C7	0.0134 (4)	0.0121 (4)	0.0139 (4)	0.0009 (3)	0.0040 (3)	0.0004 (3)
C8	0.0187 (5)	0.0151 (4)	0.0192 (5)	0.0030 (3)	0.0103 (4)	0.0030 (3)
C9	0.0198 (5)	0.0135 (4)	0.0193 (5)	0.0022 (3)	0.0078 (4)	0.0027 (3)
C10	0.0139 (5)	0.0125 (4)	0.0181 (5)	0.0020 (3)	0.0039 (4)	−0.0015 (3)
C11	0.0133 (4)	0.0174 (4)	0.0176 (5)	0.0006 (3)	0.0061 (4)	−0.0010 (3)
C12	0.0145 (4)	0.0147 (4)	0.0171 (5)	−0.0002 (3)	0.0067 (4)	0.0008 (3)
C13	0.0155 (5)	0.0123 (4)	0.0133 (4)	0.0005 (3)	0.0048 (4)	−0.0001 (3)
C14	0.0200 (5)	0.0187 (4)	0.0144 (5)	0.0060 (4)	0.0045 (4)	0.0026 (3)
C15	0.0199 (5)	0.0192 (4)	0.0131 (4)	0.0035 (4)	0.0051 (4)	0.0026 (3)
C16	0.0151 (4)	0.0142 (4)	0.0144 (4)	−0.0003 (3)	0.0067 (4)	−0.0009 (3)
C17	0.0138 (4)	0.0140 (4)	0.0148 (4)	0.0013 (3)	0.0033 (4)	0.0005 (3)
C18	0.0160 (5)	0.0152 (4)	0.0114 (4)	0.0013 (3)	0.0030 (4)	0.0009 (3)

Geometric parameters (Å, º) top

Cl1—N1	2.9827 (9)	C7—C8	1.4032 (15)
Cl2—N1	2.9848 (8)	C7—C12	1.4041 (17)
O1—N2	1.2308 (13)	C8—C9	1.3855 (14)
O2—N2	1.2307 (16)	C8—H1c8	0.96
O3—N3	1.2285 (12)	C9—C10	1.3880 (18)
O4—N3	1.2219 (12)	C9—H1c9	0.96
N1—C1	1.4256 (14)	C10—C11	1.3878 (15)
N1—C7	1.3996 (12)	C11—C12	1.3803 (14)
N1—C13	1.4087 (15)	C11—H1c11	0.96
N2—C10	1.4553 (13)	C12—H1c12	0.96
N3—C16	1.4573 (15)	C13—C14	1.4027 (14)
C1—C2	1.3991 (14)	C13—C18	1.4017 (13)
C1—C6	1.3898 (13)	C14—C15	1.3805 (17)
C2—C3	1.3901 (18)	C14—H1c14	0.96
C3—C4	1.3818 (17)	C15—C16	1.3861 (14)
C3—H1c3	0.96	C15—H1c15	0.96
C4—C5	1.3801 (17)	C16—C17	1.3858 (14)
C4—H1c4	0.96	C17—C18	1.3850 (16)
C5—C6	1.3891 (17)	C17—H1c17	0.96
C5—H1c5	0.96	C18—H1c18	0.96

Cl1—N1—Cl2	128.74 (3)	C7—C8—C9	120.08 (11)
Cl1—N1—C1	64.63 (5)	C7—C8—H1c8	119.96
Cl1—N1—C7	110.73 (6)	C9—C8—H1c8	119.96
Cl1—N1—C13	91.15 (5)	C8—C9—C10	119.33 (10)
Cl2—N1—C1	64.21 (4)	C8—C9—H1c9	120.33
Cl2—N1—C7	91.08 (5)	C10—C9—H1c9	120.33
Cl2—N1—C13	113.45 (6)	N2—C10—C9	119.43 (9)
C1—N1—C7	118.75 (9)	N2—C10—C11	119.00 (11)
C1—N1—C13	115.72 (8)	C9—C10—C11	121.52 (9)
C7—N1—C13	125.53 (9)	C10—C11—C12	119.20 (11)
O1—N2—O2	123.46 (9)	C10—C11—H1c11	120.4
O1—N2—C10	118.27 (10)	C12—C11—H1c11	120.4
O2—N2—C10	118.25 (9)	C7—C12—C11	120.43 (10)
O3—N3—O4	122.81 (11)	C7—C12—H1c12	119.78
O3—N3—C16	118.37 (9)	C11—C12—H1c12	119.78
O4—N3—C16	118.80 (9)	N1—C13—C14	121.63 (9)
N1—C1—C2	120.56 (8)	N1—C13—C18	118.72 (9)
N1—C1—C6	121.37 (9)	C14—C13—C18	119.51 (10)
C2—C1—C6	118.06 (10)	C13—C14—C15	120.04 (9)
C1—C2—C3	121.05 (9)	C13—C14—H1c14	119.98
C2—C3—C4	119.09 (10)	C15—C14—H1c14	119.98
C2—C3—H1c3	120.45	C14—C15—C16	119.31 (9)
C4—C3—H1c3	120.45	C14—C15—H1c15	120.34
C3—C4—C5	121.24 (12)	C16—C15—H1c15	120.34
C3—C4—H1c4	119.38	N3—C16—C15	118.73 (9)
C5—C4—H1c4	119.38	N3—C16—C17	119.22 (8)
C4—C5—C6	119.01 (10)	C15—C16—C17	121.94 (11)
C4—C5—H1c5	120.49	C16—C17—C18	118.70 (9)
C6—C5—H1c5	120.49	C16—C17—H1c17	120.65
C1—C6—C5	121.48 (10)	C18—C17—H1c17	120.65
N1—C7—C8	121.84 (10)	C13—C18—C17	120.48 (9)
N1—C7—C12	118.69 (9)	C13—C18—H1c18	119.76
C8—C7—C12	119.40 (9)	C17—C18—H1c18	119.76

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H1C5···O3ⁱ	0.96	2.35	3.1950 (15)	147
C12—H1C12···O2ⁱⁱ	0.96	2.48	3.3304 (15)	148

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

Experimental details

	(I)	(II)
Crystal data
Chemical formula	C₁₈H₁₁Br₂N₃O₄	C₁₈H₁₁Cl₂N₃O₄
M_r	493.1	404.2
Crystal system, space group	Monoclinic, P2₁/c	Monoclinic, P2₁/c
Temperature (K)	100	100
a, b, c (Å)	13.4705 (7), 11.6686 (6), 11.7081 (7)	13.3117 (3), 11.5460 (3), 11.7558 (3)
β (°)	107.576 (2)	108.7971 (10)
V (Å³)	1754.39 (17)	1710.46 (7)
Z	4	4
Radiation type	Mo Kα	Mo Kα
µ (mm⁻¹)	4.65	0.41
Crystal size (mm)	0.80 × 0.56 × 0.20	0.76 × 0.65 × 0.35

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2013)	Multi-scan (SADABS; Bruker, 2013)
T_min, T_max	0.055, 0.390	0.74, 0.87
No. of measured, independent and observed [I > 3σ(I)] reflections	52187, 7731, 5557	29061, 4959, 4374
R_int	0.045	0.031
(sin θ/λ)_max (Å⁻¹)	0.808	0.704

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.079, 1.36	0.034, 0.131, 1.39
No. of reflections	7731	4959
No. of parameters	244	244
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.00, −0.91	0.24, −0.23

Computer programs: APEX2 (Bruker, 2013), SAINT-Plus (Bruker, 2013), SUPERFLIP (Palatinus & Chapuis, 2007), coordinates taken from Br analogue, JANA2006 (Petříček, et al., 2006), JANA2006 (Petříček, et al., 2006), Mercury (Macrae et al., 2008), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) for (I) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H1C5···O3ⁱ	0.96	2.37	3.175 (2)	141
C12—H1C12···O2ⁱⁱ	0.96	2.49	3.347 (2)	148

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

Hydrogen-bond geometry (Å, º) for (II) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H1C5···O3ⁱ	0.96	2.35	3.1950 (15)	147
C12—H1C12···O2ⁱⁱ	0.96	2.48	3.3304 (15)	148

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

Acknowledgements

The X-ray centre of the Vienna University of Technology is acknowledged for providing access to the single-crystal diffractometer.

References

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Volume 70| Part 8| August 2014| Pages 65-67

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

Isotypic crystal structures of 2,6-di­bromo-N,N-bis­­(4-nitro­phen­yl)aniline and 2,6-di­chloro-N,N-bis­­(4-nitro­phen­yl)aniline

1. Chemical context

2. Structural commentary

3. Supra­molecular features

4. Database survey

5. Synthesis and crystallization

6. Refinement

Supporting information

Acknowledgements

References

research communications

Isotypic crystal structures of 2,6-dibromo-N,N-bis(4-nitrophenyl)aniline and 2,6-dichloro-N,N-bis(4-nitrophenyl)aniline

3. Supramolecular features