Binary and ternary charge-transfer complexes using 1,3,5-tri­nitro­benzene

Hill, T.; Levendis, D.C.; Lemmerer, A.

doi:10.1107/S2056989018000245

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Volume 74| Part 2| February 2018| Pages 113-118

https://doi.org/10.1107/S2056989018000245

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Binary and ternary charge-transfer complexes using 1,3,5-trinitrobenzene

Tania Hill,^a Demetrius C. Levendis ^a and Andreas Lemmerer ^a ^*

^aMolecular Sciences Institute, School of Chemistry, University of the Witwatersrand, Private Bag, PO WITS, 2050, Johannesburg, South Africa
^*Correspondence e-mail: andreas.lemmerer@wits.ac.za

Edited by E. V. Boldyreva, Russian Academy of Sciences, Russia (Received 29 November 2017; accepted 4 January 2018; online 9 January 2018)

Three binary and one ternary charge-transfer complexes have been made using 1,3,5-trinitrobenzene, viz. 1,3,5-trinitrobenzene–2-acetylnaphthalene (1/1), C₆H₃N₃O₆·C₁₂H₁₀O, (I), 1,3,5-trinitrobenzene–9-bromoanthracene (1/1), C₁₄H₉Br·C₆H₃N₃O₆, (II), 1,3,5-trinitrobenzene–methyl red (1/1), C₁₅H₁₅N₃O₂·C₆H₃N₃O₆, (III) (systematic name for methyl red: 2-{(E)-[4-(dimethylamino)phenyl]diazenyl}benzoic acid), and 1,3,5-trinitrobenzene–1-naphthoic acid–2-amino-5-nitropyridine (1/1/1), C₆H₃N₃O₆·C₁₁H₈O₂·C₅H₅N₃O₂, (IV). All charge-transfer complexes show alternating donor and acceptor stacks, which have weak C—H⋯O hydrogen bonds perpendicular to the stacking axis. In addition, complex (IV) is a crystal engineering attempt to modify the packing of the stacks by inserting a third molecule into the structure. This third molecule is stabilized by strong hydrogen bonds between the carboxylic acid group of the donor molecule and the pyridine acceptor molecule.

Keywords: crystal structure; charge transfer; ternary co-crystals.

CCDC references: 1814637; 1814636; 1814635; 1814634

1. Chemical context

The crystal structure of 1,3,5-trinitrobenzene (TNB), an energetic or high-explosive material, was first reported as far back as 1930 (Hertel & Romer, 1930 ). A number of structures of pure TNB have appeared since then, including a neutron diffraction study in 1972 (Choi & Abel, 1972 ). More recently, polymorphs (Thallapally et al., 2004 ) and pseudo-polymorphs of TNB (Jetti et al., 2003 ) have been reported.

Crystal engineering, the conception and synthesis of molecular solid-state structures, is fundamentally based upon the discernment and subsequent exploitation of intermolecular interactions. Thus, primarily non-covalent bonding is used to achieve the organization of molecules and ions in the solid state in order to produce materials with desired properties. The stability of an energetic material is one of the decisive factors in determining the viability of the final product, be it for fuels, propellants, pyrotechnics or explosives. If the energetic cannot be safely synthesized, handled and stored before its ultimate use, it is regarded as a failure, discarded and forgotten. Although not a forgotten but rather an old energetic material, 1,3,5-trinitrobenzene (TNB) falls into the class of energetics that are shock and heat sensitive, especially when in powdered dry form. Co-crystallization presents an opportunity to re-look at these problems for example, Guo et al. (2013a ) have shown that taking 2,4,6,8,10,12-hexanitrohexaazaisowurtzitane (CL-20) and co-crystallizing it with caprolactam (CPL) has lead to new and interesting effects on the relevant properties. The importance of crystal engineering in the stabilization of explosive materials, such as trinitrotoluene (TNT) and ethylenedinitramine, was described recently (Landenberger et al., 2010 ; Aakeröy et al., 2015 ). Recently, Chen et al. (2017 ) isolated a novel co-crystal of 1,3,5-trinitrobenzene (TNB) and 1-nitronaphthalene (NNAP), synthesized by using both solution and mechanochemical methods. The TNB/NNAP co-crystal has the largest proportion of π–π stacking interaction (12.7%). A charge-transfer complex of TNT and TNB has also been reported (Guo et al., 2013b ). The results indicate that the electronic effect has an influence on the intermolecular interactions in the co-crystal. Our study comprises of an investigation of TNB as a model energetic with various polycyclic aromatic hydrocarbons in order to observe their effect on the structural aspects of the solid state. The structure and properties of many charge-transfer (CT) complexes of TNB with a variety of aromatic molecules have been investigated (Brown et al., 1964 ; Herbstein & Kaftory, 1975 ), and reviewed by Herbstein in different sections of his book (Herbstein, 2005 ). To this end, we have synthesized four new charge-transfer co-crystals, three binary (I)–(III), and one ternary (IV): trinitrobenzene–2-acetylnaphthalene, (I), trinitrobenzene–9-bromoanthracene, (II), trinitrobenzene–methyl red, (III), and trinitrobenzene–1-naphthoic acid–2-amino-5-nitropyridine, (IV).

2. Structural commentary

The asymmetric units and atom-labelling schemes for the title charge-transfer complexes are shown in Fig. 1. All compounds have Z′ = 1 with all molecules in general positions. As a result of the strong polarizing effect of the nitro groups, TNB has an electron-poor π-system. On the other hand, the donor molecules (polycyclic aromatic hydrocarbons) have an electron-rich π-system. The packing of the unit cell of the complexes follows a donor (D) acceptor (A) π–π interaction, which is the major driving force in the formation of these complexes, as seen in Fig. 2 (donor molecules shown in blue and acceptors in green), resulting in a general face-to-face π-stacking, with Table 1 summarizing the closest centroid–centroid distances between the TNB acceptor and aromatic donor systems. The intermolecular interactions of the D⋯A stacks can be quantified using Hirschfeld surface analysis as well as the resulting fingerprint plots using the programme CrystalExplorer17.5 (Spackman & McKinnon, 2002 ). In the paper by Chen et al. (2017), the authors describe the regions of blue and red triangles on the Hirshfeld surface using the shape index as evidence of π–π interactions. Fig. 3 shows such surfaces plotted for the TNB molecules in (I)–(IV). The red triangles show concave regions indicative of ring carbons of the π-stacked molecule above it. (I) and (II) show the most triangles, indicative that they have the greatest proportion of π–π stacking of the four structures. This can be quantified by looking at the contribution that C⋯C contacts make up in the fingerprint plots. (I) and (II) have values of 12.0 and 12.6%, respectively, much greater than the 4.4 and 7.5% for (III) and (IV), respectively. Table 2 summarizes the percentages of C⋯C, H⋯H and C⋯H contacts and the relevant fingerprint plots are given in the supporting information. In terms of the molecular geometry, the TNB molecules show some changes from the geometries encountered in the pure compound. The pure compound has torsion angles of the nitro group to the benzene ring in the range from 0 to 28.17°, whereas in the CT complexes described here they range from −20.0 (4) to +20.0 (5)°. The packing and hydrogen-bonding interactions are further described below individually for each compound.

Table 1
Centroid distances (Å) between the trinitrobenzene and the ring centroids (Cg) of the aromatic polycyclics

Structure	Donor	Acceptor	Cg⋯Cg	Symmetry operator
(I)	C1–C6	C11–C20	3.3745 (2)	x, y, z
(II)	C1–C6	C11–C24	3.5173 (11)	x, y, z
(III)	C1–C6	C11–C16	3.6587 (14)	1 − x, 1 − y, 1 − z
(III)	C1–C6	C19–C24	4.6432 (18)	x, y, z
(IV)	C1–C6	C11–C20	4.0417 (8)	x, y + 1, z

Table 2
Proportion (%) of intermolecular contacts between donor and acceptor molecules in the Hirshfeld fingerprint plots

Structure	C⋯C	H⋯H	C⋯H
(I)	12.0	10.7	1.5
(II)	12.6	6.6	0.9
(III)	4.4	11.0	5.4
(IV)	7.5	8.8	4.6

Figure 1
Perspective views of compounds (I)–(IV), showing the atom-numbering schemes. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii. The dashed lines indicate the symmetry-independent N—H⋯O and O—H⋯N hydrogen bonds.

Figure 2
The packing diagrams for all four compounds (I)–(IV). The acceptor molecules are shown in green and the donor molecules in blue. The third molecule of 2-amino-5-nitropyridine is shown in red in (IV)

Figure 3
The molecular Hirshfeld surfaces mapped with shape index for the TNB acceptor molecule in (I)–(IV).

3. Supramolecular features

Structure (I) crystallizes in the P2₁/c space group with both the TNB and 2-acetylnaphthalene molecules in the asymmetric unit. The donor and acceptor molecules pack in a checker-board fashion parallel to the ab plane (Fig. 2a). In the plane perpendicular to the stacking, the ac plane, there are C—H⋯O interactions between TNB and 2-acetylnaphthalene molecules (Table 3, Fig. 4a), forming an R₃³(17) ring described using graph set notation (Bernstein et al., 1995 ).

Table 3
Hydrogen-bond geometry (Å, °) for (I)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O2ⁱ	0.93	2.4	3.189 (3)	143
C11—H11⋯O3ⁱⁱ	0.93	2.48	3.323 (4)	150
C22—H22A⋯O4ⁱⁱⁱ	0.96	2.64	3.554 (4)	159
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z+1; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Figure 4
The hydrogen-bonding diagrams for all four compounds. Atoms with superscripts (i)–(v) are at the symmetry positions (−x + 1, −y + 1, −z + 1), (−x + 1, y − $[{1\over 2}]$ , −z + $[{1\over 2}]$ ), (x, y − 1, z), (x − 1, y + 1, z) and (1 − x, −y, −z + 1) respectively.

Structure (II) crystallizes in the P2₁/c space group with both the TNB and 9-bromoanthracene in the asymmetric unit. The packing of the structure displays a clear separation of the donor (blue) and acceptor (green) layers (Fig. 2b). The alternating DA stacks show that the bromine atom of the 9-bromoanthracene packs in a head-to-head stacked fashion; however, the distance between the nearest Br atoms is very long [4.981 (1) Å], much longer than the sum of their van der Waals radii, and as a result Br⋯Br interactions are not involved in the molecular aggregation. In the plane perpendicular to the stacking, there are C—H⋯O interactions (Table 4) between TNB molecules forming an R₂²(10) ring, and a discrete hydrogen bond between the TNB and 9-bromoanthracene molecules (Fig. 4b).

Table 4
Hydrogen-bond geometry (Å, °) for (II)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O6ⁱ	0.95	2.5	3.287 (3)	140
C6—H6⋯O5ⁱⁱ	0.95	2.68	3.593 (3)	162
C14—H14⋯O4ⁱⁱⁱ	0.95	2.57	3.255 (3)	129
C21—H21⋯O1^iv	0.95	2.65	3.364 (3)	132
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) x, y+1, z; (iv) x+1, y-1, z.

Structure (III) crystallizes in the P $[\overline{1}]$ space group with both the TNB and the methyl red in the asymmetric unit. The packing of the structure illustrates that for each phenyl ring on the methyl red molecule, there is an associated TNB molecule. The two TNB molecules are at different distances from the ring centroids, with a variation of ca 0.98 Å (Table 2). Along the bc plane, the TNB molecules display similar hydrogen-bonded rings as those observed for (II) (Fig. 2c), and an additional six-membered intramolecular S(6) hydrogen bond is found (Fig. 1c). The TNB and methyl red molecules are again joined by C—H⋯O hydrogen bonds (Table 5) to the nitro oxygen atoms, forming an R₂²(11) ring (Fig. 4c).

Table 5
Hydrogen-bond geometry (Å, °) for (III)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O4ⁱ	0.95	2.35	3.285 (4)	169
C15—H15⋯O11ⁱⁱ	0.95	2.34	3.254 (4)	161
C18—H18A⋯O11ⁱⁱ	0.98	2.55	3.519 (4)	170
C20—H20⋯O3ⁱⁱⁱ	0.95	2.64	3.574 (4)	167
O12—H12⋯N12	0.95 (6)	1.70 (6)	2.577 (3)	153 (5)
C21—H21⋯O2ⁱⁱⁱ	0.95	2.56	3.469 (4)	161
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x, -y+1, -z+1; (iii) -x+1, -y, -z+1.

Structure (IV) crystallizes in the P $[\overline{1}]$ space group with the TNB, 1-naphthoic and 2-amino-5-nitropyridine molecules in the asymmetric unit. The addition of a third molecule into this charge-transfer complex results in groups of alternating DA stacks separated by the added pyridine component (Fig. 2d). The TNB molecules are joined by R₂¹(6) rings, whereas a strong hydrogen-bonding interaction between the DA stacks and the 2-amino-5-nitropyridine molecule was found, forming an R₂²(8) ring, as well as a weaker bifurcated C—H⋯O R₁²(4) ring (Table 6, Fig. 4d); interestingly there is no additional DA stacking with the 1-naphthoic and the pyridine components.

Table 6
Hydrogen-bond geometry (Å, °) for (IV)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5A⋯O8	0.90 (5)	2.03 (5)	2.919 (5)	168 (5)
N5—H5B⋯O9ⁱ	0.86 (4)	2.24 (4)	3.069 (5)	161 (4)
O7—H7⋯N4	0.95 (5)	1.71 (5)	2.650 (4)	171 (5)
C23—H23⋯O9ⁱ	0.95	2.5	3.272 (5)	139
C26—H26⋯O1	0.95	2.69	3.530 (5)	147
C26—H26⋯O2	0.95	2.72	3.477 (5)	138
Symmetry code: (i) x, y-1, z.

In summary, we have contributed to the field of CT complexes using TNB, presenting further evidence that TNB is an ideal acceptor and, when paired with a donor that has hydrogen-bonding functionality, can be used to make ternary complexes.

4. Database survey

A database survey in the Cambridge Structural Database (CSD, Version 5.38; April 2017 update; Groom et al., 2016 ) was undertaken for any structures containing the 1,3,5-trinitrobenzene moiety. A total of 135 hits where found, which was then reduced to 95 by evaluating if there is evidence of π–π interactions as indicative for a CT complex.

5. Synthesis and crystallization

All chemicals were purchased from commercial sources (Sigma Aldrich) and used as received without further purification. The 1,3,5-trinitrobenzene charge-transfer complexes were prepared in a 10 mL ethanolic solution with a 1:1 or 1:1:1 stoichiometric ratio of the donor to the acceptor molecule (based on 0.469 mmol of TNB), which was then heated until total dissolution took place (approx. 4 h). The solution was then cooled very slowly to obtain crystals suitable for X-ray diffraction. Detailed masses are as follows: (I): 0.100 g of 1,3,5-trinitrobenzene and 0.080 g of 2-acetylnaphthalene; (II): 0.100 g of 1,3,5-trinitrobenzene and 0.121 g of 9-bromoanthracene; (III): 0.100 g of 1,3,5-trinitrobenzene and 0.127 g of methyl red; and (IV): 0.100 g of 1,3,5-trinitrobenzene, 0.081 of 1-naphthoic acid and 0.065 g of 2-amino-5-nitropyridine.

6. Refinement details

Crystal data, data collection and structure refinement details are summarized in Table 7. For all compounds, the C-bound H atoms were placed geometrically [C—H bond lengths of 0.96 (methyl CH₃), and 0.95 Å (Ar—H)] and refined as riding with U_iso(H) = 1.2U_eq(Ar-C) or U_iso(H) = 1.5U_eq(methyl-C). The O and N–bound H atoms were located in the difference map and their coordinates and isotropic displacement parameters allowed to refine freely.

Table 7
Experimental details

	(I)	(II)	(III)	(IV)
Crystal data
Chemical formula	C₆H₃N₃O₆·C₁₂H₁₀O	C₁₄H₉Br·C₆H₃N₃O₆	C₁₅H₁₅N₃O₂·C₆H₃N₃O₆	C₆H₃N₃O₆·C₁₁H₈O₂·C₅H₅N₃O₂
M_r	383.31	470.24	482.41	524.41
Crystal system, space group	Monoclinic, P2₁/c	Monoclinic, P2₁/c	Triclinic, P $[\overline{1}]$	Triclinic, P $[\overline{1}]$
Temperature (K)	293	173	173	173
a, b, c (Å)	16.6728 (10), 6.8197 (3), 15.4419 (7)	7.0928 (2), 9.7701 (3), 27.0563 (7)	8.550 (3), 10.437 (3), 13.072 (5)	7.5365 (15), 7.9003 (16), 19.153 (4)
α, β, γ (°)	90, 102.217 (3), 90	90, 100.674 (1), 90	110.689 (10), 103.510 (12), 90.730 (12)	97.580 (7), 94.667 (6), 99.547 (7)
V (Å³)	1716.03 (15)	1842.49 (9)	1055.2 (7)	1108.5 (4)
Z	4	4	2	2
Radiation type	Mo Kα	Mo Kα	Mo Kα	Mo Kα
μ (mm⁻¹)	0.12	2.28	0.12	0.13
Crystal size (mm)	0.15 × 0.12 × 0.07	0.33 × 0.12 × 0.11	0.29 × 0.13 × 0.12	0.63 × 0.33 × 0.06

Data collection
Diffractometer	Bruker D8 Venture Photon CCD area detector	Bruker D8 Venture Photon CCD area detector	Bruker D8 Venture Photon CCD area detector	Bruker D8 Venture Photon CCD area detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996 )	Multi-scan (SADABS; Sheldrick, 1996)	Multi-scan (SADABS; Sheldrick, 1996)	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.9, 0.95	0.56, 0.77	0.9, 0.95	0.9, 0.95
No. of measured, independent and observed [I > 2σ(I)] reflections	15612, 3195, 1874	28424, 4450, 3758	39527, 5072, 3262	12982, 3988, 3368
R_int	0.063	0.048	0.072	0.034

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.152, 1.01	0.040, 0.096, 1.08	0.078, 0.249, 1.07	0.072, 0.168, 1.22
No. of reflections	3195	4450	5072	3988
No. of parameters	254	271	322	355
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained	H atoms treated by a mixture of independent and constrained refinement	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.29	1.42, −0.94	0.49, −0.43	0.32, −0.37
Computer programs: APEX3, SAINT-Plus and XPREP (Bruker, 2016 ), SHELXS97 (Sheldrick, 2015 ), SHELXL2017/1 (Sheldrick, 2015), ORTEP-3 for Windows and WinGX publication routines (Farrugia, 2012 ) and Mercury (Macrae et al., 2006 ).

Supporting information

CCDC references: 1814637; 1814636; 1814635; 1814634

Crystal structure: contains datablocks I, II, III, IV, shelx. DOI: https://doi.org/10.1107/S2056989018000245/eb2004sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989018000245/eb2004Isup2.hkl

Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S2056989018000245/eb2004IIsup3.hkl

Structure factors: contains datablock III. DOI: https://doi.org/10.1107/S2056989018000245/eb2004IIIsup4.hkl

Structure factors: contains datablock IV. DOI: https://doi.org/10.1107/S2056989018000245/eb2004IVsup5.hkl

Fingerprint plots. DOI: https://doi.org/10.1107/S2056989018000245/eb2004sup6.pdf

Supporting information file. DOI: https://doi.org/10.1107/S2056989018000245/eb2004Isup7.cml

Supporting information file. DOI: https://doi.org/10.1107/S2056989018000245/eb2004IIsup8.cml

Supporting information file. DOI: https://doi.org/10.1107/S2056989018000245/eb2004IIIsup9.cml

Supporting information file. DOI: https://doi.org/10.1107/S2056989018000245/eb2004IVsup10.cml

checkCIF report

Computing details top

For all structures, data collection: APEX3 (Bruker, 2016); cell refinement: SAINT-Plus (Bruker, 2016); data reduction: SAINT-Plus and XPREP (Bruker, 2016). Program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) for (I); SHELXS97 (Sheldrick, 2015) for (II), (III), (IV). For all structures, program(s) used to refine structure: SHELXL2017/1 (Sheldrick, 2015). Molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) for (I); ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006) for (II), (III), (IV). For all structures, software used to prepare material for publication: WinGX publication routines (Farrugia, 2012).

1,3,5-Trinitrobenzene–1-(naphthalen-2-yl)ethan-1-one (1/1) (I) top

Crystal data top

C₆H₃N₃O₆·C₁₂H₁₀O	F(000) = 792
M_r = 383.31	D_x = 1.484 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1787 reflections
a = 16.6728 (10) Å	θ = 2.5–19.9°
b = 6.8197 (3) Å	µ = 0.12 mm⁻¹
c = 15.4419 (7) Å	T = 293 K
β = 102.217 (3)°	Plate, yellow
V = 1716.03 (15) Å³	0.15 × 0.12 × 0.07 mm
Z = 4

Data collection top

Bruker D8 Venture Photon CCD area detector diffractometer	1874 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.063
ω scans	θ_max = 25.5°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→20
T_min = 0.9, T_max = 0.95	k = −8→8
15612 measured reflections	l = −18→18
3195 independent reflections

Refinement top

Refinement on F²	0 constraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.053	H-atom parameters constrained
wR(F²) = 0.152	w = 1/[σ²(F_o²) + (0.0652P)² + 0.4622P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
3195 reflections	Δρ_max = 0.40 e Å⁻³
254 parameters	Δρ_min = −0.28 e Å⁻³
0 restraints

Special details top

Experimental. (SADABS; Sheldrick, 1996)

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

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

	x	y	z	U_iso*/U_eq
C1	0.21511 (18)	0.3392 (4)	0.53179 (17)	0.0389 (7)
C2	0.29340 (17)	0.3382 (4)	0.51644 (18)	0.0405 (7)
H2	0.338939	0.313665	0.561495	0.049*
C3	0.30078 (16)	0.3753 (4)	0.43143 (18)	0.0375 (6)
C4	0.23515 (17)	0.4104 (3)	0.36307 (17)	0.0380 (7)
H4	0.242162	0.435636	0.305949	0.046*
C5	0.15851 (17)	0.4066 (3)	0.38276 (17)	0.0373 (6)
C6	0.14629 (17)	0.3724 (3)	0.46663 (17)	0.0393 (7)
H6	0.093996	0.371735	0.478805	0.047*
N1	0.2053 (2)	0.3015 (4)	0.62306 (17)	0.0552 (7)
N2	0.38409 (17)	0.3748 (3)	0.4122 (2)	0.0530 (7)
N3	0.08572 (17)	0.4407 (4)	0.31102 (18)	0.0552 (7)
O1	0.14078 (18)	0.3516 (4)	0.64216 (16)	0.0780 (8)
O2	0.26172 (18)	0.2195 (3)	0.67273 (14)	0.0753 (8)
O3	0.44113 (14)	0.3279 (3)	0.47247 (19)	0.0778 (8)
O4	0.39003 (15)	0.4197 (4)	0.33769 (17)	0.0748 (7)
O5	0.09752 (15)	0.5061 (3)	0.24181 (15)	0.0707 (7)
O6	0.01788 (16)	0.4066 (4)	0.32863 (18)	0.0871 (8)
C11	0.37425 (18)	0.8616 (4)	0.44847 (17)	0.0416 (7)
H11	0.431199	0.855588	0.46446	0.05*
C12	0.33560 (17)	0.8871 (4)	0.35789 (17)	0.0386 (6)
C13	0.25164 (17)	0.9004 (4)	0.33542 (18)	0.0399 (7)
H13	0.225873	0.918682	0.276412	0.048*
C14	0.20357 (16)	0.8866 (3)	0.40060 (17)	0.0355 (6)
C15	0.11648 (17)	0.8960 (4)	0.37776 (19)	0.0447 (7)
H15	0.090008	0.917791	0.319232	0.054*
C16	0.07171 (19)	0.8732 (4)	0.4412 (2)	0.0491 (8)
H16	0.014733	0.878211	0.425528	0.059*
C17	0.11022 (19)	0.8425 (4)	0.5296 (2)	0.0490 (8)
H17	0.078694	0.827225	0.572177	0.059*
C18	0.19420 (19)	0.8348 (4)	0.55427 (19)	0.0437 (7)
H18	0.2192	0.815473	0.61345	0.052*
C19	0.24309 (17)	0.8560 (3)	0.49009 (17)	0.0363 (6)
C20	0.32950 (17)	0.8457 (4)	0.51201 (18)	0.0402 (7)
H20	0.356146	0.827898	0.57077	0.048*
C21	0.3838 (2)	0.8968 (4)	0.2863 (2)	0.0473 (7)
C22	0.4755 (2)	0.9057 (5)	0.3127 (2)	0.0672 (10)
H22A	0.498045	0.917132	0.260632	0.101*
H22B	0.495732	0.788375	0.344169	0.101*
H22C	0.491439	1.017472	0.350196	0.101*
O7	0.34871 (15)	0.8966 (3)	0.20881 (14)	0.0650 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0476 (19)	0.0333 (14)	0.0369 (15)	−0.0045 (12)	0.0118 (14)	−0.0014 (11)
C2	0.0381 (18)	0.0357 (14)	0.0434 (16)	0.0008 (12)	−0.0011 (14)	−0.0009 (12)
C3	0.0303 (16)	0.0325 (13)	0.0510 (17)	0.0010 (11)	0.0114 (14)	−0.0037 (12)
C4	0.0447 (19)	0.0346 (14)	0.0363 (14)	0.0034 (12)	0.0121 (14)	−0.0028 (11)
C5	0.0352 (17)	0.0306 (13)	0.0421 (15)	0.0039 (11)	−0.0007 (13)	−0.0036 (11)
C6	0.0346 (17)	0.0345 (14)	0.0502 (17)	−0.0023 (12)	0.0121 (14)	−0.0070 (12)
N1	0.073 (2)	0.0471 (15)	0.0475 (16)	−0.0166 (14)	0.0164 (16)	−0.0030 (12)
N2	0.0416 (17)	0.0424 (14)	0.078 (2)	0.0023 (12)	0.0204 (16)	−0.0066 (13)
N3	0.0462 (19)	0.0524 (15)	0.0570 (17)	0.0066 (13)	−0.0114 (14)	−0.0043 (13)
O1	0.095 (2)	0.0840 (17)	0.0698 (16)	−0.0071 (15)	0.0500 (16)	−0.0035 (13)
O2	0.097 (2)	0.0782 (16)	0.0457 (13)	−0.0164 (15)	0.0035 (14)	0.0144 (12)
O3	0.0317 (14)	0.0797 (16)	0.118 (2)	0.0058 (12)	0.0062 (15)	0.0163 (15)
O4	0.0642 (18)	0.0922 (18)	0.0813 (17)	−0.0031 (13)	0.0449 (15)	−0.0105 (14)
O5	0.0794 (19)	0.0802 (16)	0.0436 (12)	0.0271 (13)	−0.0073 (13)	0.0002 (12)
O6	0.0373 (16)	0.101 (2)	0.112 (2)	−0.0084 (14)	−0.0087 (15)	0.0112 (16)
C11	0.0329 (16)	0.0417 (15)	0.0488 (17)	0.0003 (12)	0.0056 (14)	−0.0014 (12)
C12	0.0349 (17)	0.0365 (14)	0.0451 (16)	−0.0017 (12)	0.0102 (13)	−0.0027 (12)
C13	0.0406 (18)	0.0362 (14)	0.0407 (15)	0.0010 (12)	0.0038 (13)	−0.0014 (12)
C14	0.0290 (16)	0.0292 (12)	0.0461 (16)	0.0018 (11)	0.0032 (13)	−0.0040 (11)
C15	0.0361 (18)	0.0404 (15)	0.0538 (17)	0.0053 (12)	0.0010 (15)	−0.0034 (13)
C16	0.0349 (18)	0.0454 (16)	0.068 (2)	0.0061 (13)	0.0131 (16)	−0.0054 (15)
C17	0.044 (2)	0.0430 (16)	0.066 (2)	0.0039 (13)	0.0249 (17)	−0.0054 (14)
C18	0.049 (2)	0.0382 (15)	0.0456 (16)	0.0023 (13)	0.0137 (15)	−0.0019 (12)
C19	0.0359 (17)	0.0307 (14)	0.0413 (15)	0.0020 (11)	0.0063 (13)	−0.0026 (11)
C20	0.0381 (18)	0.0401 (14)	0.0396 (15)	0.0016 (12)	0.0016 (13)	0.0004 (12)
C21	0.052 (2)	0.0463 (16)	0.0466 (18)	0.0000 (14)	0.0180 (16)	−0.0048 (14)
C22	0.046 (2)	0.095 (3)	0.067 (2)	−0.0053 (19)	0.0274 (18)	−0.0026 (19)
O7	0.0648 (16)	0.0863 (16)	0.0466 (13)	−0.0020 (13)	0.0180 (12)	−0.0060 (11)

Geometric parameters (Å, º) top

C1—C2	1.375 (4)	C12—C13	1.372 (4)
C1—C6	1.375 (4)	C12—C21	1.500 (4)
C1—N1	1.475 (4)	C13—C14	1.416 (4)
C2—C3	1.368 (4)	C13—H13	0.93
C2—H2	0.93	C14—C19	1.415 (4)
C3—C4	1.371 (4)	C14—C15	1.421 (4)
C3—N2	1.481 (4)	C15—C16	1.361 (4)
C4—C5	1.375 (4)	C15—H15	0.93
C4—H4	0.93	C16—C17	1.396 (4)
C5—C6	1.373 (4)	C16—H16	0.93
C5—N3	1.478 (4)	C17—C18	1.372 (4)
C6—H6	0.93	C17—H17	0.93
N1—O2	1.217 (4)	C18—C19	1.418 (4)
N1—O1	1.222 (3)	C18—H18	0.93
N2—O4	1.214 (3)	C19—C20	1.410 (4)
N2—O3	1.224 (3)	C20—H20	0.93
N3—O5	1.212 (3)	C21—O7	1.215 (3)
N3—O6	1.240 (3)	C21—C22	1.497 (4)
C11—C20	1.357 (4)	C22—H22A	0.96
C11—C12	1.422 (4)	C22—H22B	0.96
C11—H11	0.93	C22—H22C	0.96

C2—C1—C6	123.4 (2)	C12—C13—C14	121.1 (3)
C2—C1—N1	117.7 (3)	C12—C13—H13	119.5
C6—C1—N1	118.9 (3)	C14—C13—H13	119.5
C3—C2—C1	116.5 (3)	C19—C14—C13	119.2 (2)
C3—C2—H2	121.8	C19—C14—C15	119.3 (2)
C1—C2—H2	121.8	C13—C14—C15	121.5 (2)
C2—C3—C4	123.5 (2)	C16—C15—C14	120.2 (3)
C2—C3—N2	118.1 (3)	C16—C15—H15	119.9
C4—C3—N2	118.4 (2)	C14—C15—H15	119.9
C3—C4—C5	117.0 (2)	C15—C16—C17	120.8 (3)
C3—C4—H4	121.5	C15—C16—H16	119.6
C5—C4—H4	121.5	C17—C16—H16	119.6
C6—C5—C4	122.8 (3)	C18—C17—C16	120.5 (3)
C6—C5—N3	118.1 (3)	C18—C17—H17	119.7
C4—C5—N3	119.0 (2)	C16—C17—H17	119.7
C5—C6—C1	116.8 (3)	C17—C18—C19	120.4 (3)
C5—C6—H6	121.6	C17—C18—H18	119.8
C1—C6—H6	121.6	C19—C18—H18	119.8
O2—N1—O1	125.4 (3)	C20—C19—C14	118.9 (2)
O2—N1—C1	117.0 (3)	C20—C19—C18	122.4 (2)
O1—N1—C1	117.6 (3)	C14—C19—C18	118.7 (3)
O4—N2—O3	125.5 (3)	C11—C20—C19	120.8 (3)
O4—N2—C3	117.2 (3)	C11—C20—H20	119.6
O3—N2—C3	117.3 (3)	C19—C20—H20	119.6
O5—N3—O6	126.0 (3)	O7—C21—C22	121.3 (3)
O5—N3—C5	117.3 (3)	O7—C21—C12	120.2 (3)
O6—N3—C5	116.6 (3)	C22—C21—C12	118.4 (3)
C20—C11—C12	121.1 (3)	C21—C22—H22A	109.5
C20—C11—H11	119.4	C21—C22—H22B	109.5
C12—C11—H11	119.4	H22A—C22—H22B	109.5
C13—C12—C11	118.9 (2)	C21—C22—H22C	109.5
C13—C12—C21	119.2 (3)	H22A—C22—H22C	109.5
C11—C12—C21	121.9 (3)	H22B—C22—H22C	109.5

C6—C1—C2—C3	0.9 (4)	C20—C11—C12—C13	1.5 (4)
N1—C1—C2—C3	−179.4 (2)	C20—C11—C12—C21	−177.5 (2)
C1—C2—C3—C4	−0.6 (4)	C11—C12—C13—C14	−0.8 (4)
C1—C2—C3—N2	−179.8 (2)	C21—C12—C13—C14	178.3 (2)
C2—C3—C4—C5	−0.3 (4)	C12—C13—C14—C19	−0.9 (3)
N2—C3—C4—C5	178.9 (2)	C12—C13—C14—C15	−178.7 (2)
C3—C4—C5—C6	0.9 (4)	C19—C14—C15—C16	−0.9 (4)
C3—C4—C5—N3	−179.1 (2)	C13—C14—C15—C16	176.9 (2)
C4—C5—C6—C1	−0.7 (4)	C14—C15—C16—C17	0.7 (4)
N3—C5—C6—C1	179.4 (2)	C15—C16—C17—C18	0.0 (4)
C2—C1—C6—C5	−0.2 (4)	C16—C17—C18—C19	−0.6 (4)
N1—C1—C6—C5	−179.9 (2)	C13—C14—C19—C20	1.8 (3)
C2—C1—N1—O2	−20.0 (4)	C15—C14—C19—C20	179.6 (2)
C6—C1—N1—O2	159.7 (3)	C13—C14—C19—C18	−177.6 (2)
C2—C1—N1—O1	161.3 (3)	C15—C14—C19—C18	0.3 (3)
C6—C1—N1—O1	−19.0 (4)	C17—C18—C19—C20	−178.9 (2)
C2—C3—N2—O4	−175.6 (2)	C17—C18—C19—C14	0.4 (4)
C4—C3—N2—O4	5.2 (4)	C12—C11—C20—C19	−0.6 (4)
C2—C3—N2—O3	4.9 (4)	C14—C19—C20—C11	−1.1 (3)
C4—C3—N2—O3	−174.4 (2)	C18—C19—C20—C11	178.2 (2)
C6—C5—N3—O5	166.6 (2)	C13—C12—C21—O7	−7.3 (4)
C4—C5—N3—O5	−13.4 (3)	C11—C12—C21—O7	171.7 (3)
C6—C5—N3—O6	−10.7 (4)	C13—C12—C21—C22	173.0 (3)
C4—C5—N3—O6	169.3 (3)	C11—C12—C21—C22	−8.0 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O2ⁱ	0.93	2.4	3.189 (3)	143
C11—H11···O3ⁱⁱ	0.93	2.48	3.323 (4)	150
C22—H22A···O4ⁱⁱⁱ	0.96	2.64	3.554 (4)	159

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

1,3,5-Trinitrobenzene–9-bromoanthracene (1/1) (II) top

Crystal data top

C₁₄H₉Br·C₆H₃N₃O₆	F(000) = 944
M_r = 470.24	D_x = 1.695 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8164 reflections
a = 7.0928 (2) Å	θ = 2.2–27.9°
b = 9.7701 (3) Å	µ = 2.28 mm⁻¹
c = 27.0563 (7) Å	T = 173 K
β = 100.674 (1)°	Needle, yellow
V = 1842.49 (9) Å³	0.33 × 0.12 × 0.11 mm
Z = 4

Data collection top

Bruker D8 Venture Photon CCD area detector diffractometer	3758 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.048
ω scans	θ_max = 28.0°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.56, T_max = 0.77	k = −12→12
28424 measured reflections	l = −35→35
4450 independent reflections

Refinement top

Refinement on F²	0 constraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.040	H-atom parameters constrained
wR(F²) = 0.096	w = 1/[σ²(F_o²) + (0.0343P)² + 2.1935P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max < 0.001
4450 reflections	Δρ_max = 1.42 e Å⁻³
271 parameters	Δρ_min = −0.94 e Å⁻³
0 restraints

Special details top

Experimental. (SADABS; Sheldrick, 1996)

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

	x	y	z	U_iso*/U_eq
C1	0.3620 (3)	0.7554 (2)	0.10545 (9)	0.0275 (5)
C2	0.3965 (3)	0.6350 (2)	0.08161 (9)	0.0256 (5)
H2	0.369113	0.62674	0.046011	0.031*
C3	0.4723 (3)	0.5280 (2)	0.11194 (9)	0.0236 (4)
C4	0.5164 (3)	0.5366 (2)	0.16372 (9)	0.0267 (5)
H4	0.568061	0.460884	0.183771	0.032*
C5	0.4822 (4)	0.6599 (3)	0.18498 (9)	0.0293 (5)
C6	0.4047 (4)	0.7724 (2)	0.15702 (10)	0.0303 (5)
H6	0.382248	0.856585	0.172517	0.036*
N1	0.2782 (3)	0.8716 (2)	0.07398 (10)	0.0370 (5)
N2	0.5097 (3)	0.3967 (2)	0.08822 (8)	0.0290 (4)
N3	0.5319 (4)	0.6732 (2)	0.24030 (8)	0.0401 (6)
O1	0.2533 (3)	0.9777 (2)	0.09572 (9)	0.0543 (6)
O2	0.2376 (3)	0.8538 (2)	0.02904 (9)	0.0519 (6)
O3	0.4729 (3)	0.3904 (2)	0.04231 (7)	0.0396 (4)
O4	0.5756 (3)	0.30406 (19)	0.11577 (8)	0.0434 (5)
O5	0.5774 (5)	0.5714 (2)	0.26496 (8)	0.0654 (7)
O6	0.5271 (4)	0.7868 (3)	0.25776 (9)	0.0634 (7)
C11	0.9660 (3)	0.6511 (2)	0.16436 (8)	0.0235 (4)
C12	0.8864 (3)	0.7691 (2)	0.13900 (8)	0.0231 (4)
C13	0.8514 (4)	0.8940 (2)	0.16310 (9)	0.0305 (5)
H13	0.883923	0.900938	0.198681	0.037*
C14	0.7719 (4)	1.0031 (2)	0.13575 (10)	0.0338 (6)
H14	0.748685	1.084959	0.15261	0.041*
C15	0.7233 (4)	0.9972 (3)	0.08274 (10)	0.0319 (5)
H15	0.668981	1.074876	0.064272	0.038*
C16	0.7543 (3)	0.8804 (2)	0.05821 (9)	0.0285 (5)
H16	0.721939	0.877421	0.02255	0.034*
C17	0.8346 (3)	0.7622 (2)	0.08509 (8)	0.0223 (4)
C18	0.8607 (3)	0.6406 (2)	0.06047 (8)	0.0239 (5)
H18	0.824385	0.636703	0.024888	0.029*
C19	0.9385 (3)	0.5241 (2)	0.08641 (8)	0.0226 (4)
C20	0.9636 (3)	0.4002 (2)	0.06075 (9)	0.0274 (5)
H20	0.924336	0.396003	0.02525	0.033*
C21	1.0428 (4)	0.2876 (3)	0.08608 (10)	0.0322 (5)
H21	1.058174	0.205658	0.068314	0.039*
C22	1.1019 (4)	0.2928 (3)	0.13873 (10)	0.0319 (5)
H22	1.159053	0.214283	0.156067	0.038*
C23	1.0789 (3)	0.4077 (2)	0.16519 (9)	0.0282 (5)
H23	1.118668	0.408027	0.200702	0.034*
C24	0.9956 (3)	0.5283 (2)	0.14027 (8)	0.0224 (4)
Br1	1.03399 (4)	0.65915 (3)	0.23592 (2)	0.03853 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0215 (11)	0.0233 (11)	0.0390 (13)	0.0012 (9)	0.0088 (10)	0.0050 (10)
C2	0.0224 (11)	0.0255 (12)	0.0296 (11)	−0.0013 (9)	0.0067 (9)	0.0014 (9)
C3	0.0203 (10)	0.0211 (11)	0.0306 (11)	−0.0022 (8)	0.0075 (9)	−0.0027 (9)
C4	0.0268 (12)	0.0232 (11)	0.0307 (12)	−0.0006 (9)	0.0068 (9)	0.0009 (9)
C5	0.0297 (12)	0.0287 (12)	0.0301 (12)	−0.0045 (10)	0.0071 (10)	−0.0041 (10)
C6	0.0309 (13)	0.0228 (12)	0.0393 (13)	−0.0013 (10)	0.0121 (10)	−0.0064 (10)
N1	0.0296 (11)	0.0304 (12)	0.0515 (14)	0.0040 (9)	0.0094 (10)	0.0117 (10)
N2	0.0264 (10)	0.0259 (10)	0.0353 (11)	−0.0005 (8)	0.0076 (8)	−0.0060 (9)
N3	0.0492 (14)	0.0377 (13)	0.0331 (12)	−0.0039 (11)	0.0068 (10)	−0.0095 (10)
O1	0.0568 (14)	0.0288 (11)	0.0759 (16)	0.0161 (10)	0.0087 (12)	0.0048 (10)
O2	0.0588 (14)	0.0489 (13)	0.0476 (13)	0.0129 (11)	0.0091 (10)	0.0208 (10)
O3	0.0412 (11)	0.0416 (11)	0.0347 (10)	0.0031 (9)	0.0040 (8)	−0.0129 (8)
O4	0.0580 (13)	0.0250 (9)	0.0485 (12)	0.0132 (9)	0.0136 (10)	0.0009 (8)
O5	0.116 (2)	0.0441 (13)	0.0327 (11)	−0.0039 (13)	0.0041 (12)	0.0036 (10)
O6	0.0894 (19)	0.0487 (13)	0.0455 (13)	0.0123 (13)	−0.0048 (12)	−0.0221 (11)
C11	0.0252 (11)	0.0260 (11)	0.0195 (10)	0.0006 (9)	0.0044 (8)	0.0025 (8)
C12	0.0239 (11)	0.0214 (11)	0.0242 (11)	0.0001 (9)	0.0047 (9)	0.0014 (8)
C13	0.0406 (14)	0.0230 (11)	0.0279 (12)	0.0002 (10)	0.0061 (10)	−0.0032 (9)
C14	0.0423 (15)	0.0183 (11)	0.0409 (14)	0.0006 (10)	0.0077 (11)	−0.0026 (10)
C15	0.0334 (13)	0.0232 (12)	0.0388 (13)	0.0023 (10)	0.0062 (10)	0.0078 (10)
C16	0.0297 (12)	0.0277 (12)	0.0275 (11)	0.0021 (10)	0.0042 (9)	0.0061 (9)
C17	0.0199 (10)	0.0233 (11)	0.0245 (10)	−0.0006 (8)	0.0060 (8)	0.0031 (8)
C18	0.0225 (11)	0.0290 (12)	0.0207 (10)	0.0019 (9)	0.0053 (8)	0.0003 (8)
C19	0.0188 (10)	0.0242 (11)	0.0260 (11)	0.0005 (8)	0.0071 (8)	−0.0003 (9)
C20	0.0249 (11)	0.0286 (12)	0.0300 (12)	−0.0002 (9)	0.0086 (9)	−0.0047 (10)
C21	0.0301 (13)	0.0227 (11)	0.0465 (15)	0.0021 (10)	0.0146 (11)	−0.0055 (10)
C22	0.0309 (13)	0.0219 (11)	0.0443 (14)	0.0046 (10)	0.0103 (11)	0.0073 (10)
C23	0.0274 (12)	0.0252 (12)	0.0319 (12)	0.0020 (9)	0.0056 (10)	0.0057 (9)
C24	0.0197 (10)	0.0216 (11)	0.0267 (11)	0.0000 (8)	0.0061 (8)	0.0019 (8)
Br1	0.05475 (19)	0.03823 (16)	0.02111 (13)	0.01206 (12)	0.00313 (10)	0.00126 (10)

Geometric parameters (Å, º) top

C1—C6	1.382 (4)	C12—C17	1.438 (3)
C1—C2	1.385 (3)	C13—C14	1.359 (3)
C1—N1	1.477 (3)	C13—H13	0.95
C2—C3	1.376 (3)	C14—C15	1.413 (4)
C2—H2	0.95	C14—H14	0.95
C3—C4	1.381 (3)	C15—C16	1.358 (4)
C3—N2	1.480 (3)	C15—H15	0.95
C4—C5	1.376 (3)	C16—C17	1.426 (3)
C4—H4	0.95	C16—H16	0.95
C5—C6	1.388 (3)	C17—C18	1.391 (3)
C5—N3	1.479 (3)	C18—C19	1.396 (3)
C6—H6	0.95	C18—H18	0.95
N1—O2	1.209 (3)	C19—C20	1.423 (3)
N1—O1	1.221 (3)	C19—C24	1.439 (3)
N2—O4	1.210 (3)	C20—C21	1.362 (4)
N2—O3	1.222 (3)	C20—H20	0.95
N3—O5	1.208 (3)	C21—C22	1.409 (4)
N3—O6	1.209 (3)	C21—H21	0.95
C11—C24	1.400 (3)	C22—C23	1.358 (4)
C11—C12	1.405 (3)	C22—H22	0.95
C11—Br1	1.908 (2)	C23—C24	1.430 (3)
C12—C13	1.426 (3)	C23—H23	0.95

C6—C1—C2	123.2 (2)	C12—C13—H13	119.6
C6—C1—N1	118.6 (2)	C13—C14—C15	121.3 (2)
C2—C1—N1	118.1 (2)	C13—C14—H14	119.4
C3—C2—C1	116.8 (2)	C15—C14—H14	119.4
C3—C2—H2	121.6	C16—C15—C14	119.9 (2)
C1—C2—H2	121.6	C16—C15—H15	120
C2—C3—C4	123.3 (2)	C14—C15—H15	120
C2—C3—N2	118.8 (2)	C15—C16—C17	121.1 (2)
C4—C3—N2	117.9 (2)	C15—C16—H16	119.4
C5—C4—C3	117.0 (2)	C17—C16—H16	119.4
C5—C4—H4	121.5	C18—C17—C16	121.6 (2)
C3—C4—H4	121.5	C18—C17—C12	119.6 (2)
C4—C5—C6	123.2 (2)	C16—C17—C12	118.8 (2)
C4—C5—N3	118.2 (2)	C17—C18—C19	122.1 (2)
C6—C5—N3	118.6 (2)	C17—C18—H18	119
C1—C6—C5	116.4 (2)	C19—C18—H18	119
C1—C6—H6	121.8	C18—C19—C20	121.5 (2)
C5—C6—H6	121.8	C18—C19—C24	119.8 (2)
O2—N1—O1	125.3 (2)	C20—C19—C24	118.8 (2)
O2—N1—C1	117.7 (2)	C21—C20—C19	121.3 (2)
O1—N1—C1	117.0 (2)	C21—C20—H20	119.4
O4—N2—O3	125.0 (2)	C19—C20—H20	119.4
O4—N2—C3	117.4 (2)	C20—C21—C22	119.8 (2)
O3—N2—C3	117.6 (2)	C20—C21—H21	120.1
O5—N3—O6	124.3 (2)	C22—C21—H21	120.1
O5—N3—C5	118.4 (2)	C23—C22—C21	121.4 (2)
O6—N3—C5	117.2 (2)	C23—C22—H22	119.3
C24—C11—C12	123.9 (2)	C21—C22—H22	119.3
C24—C11—Br1	118.43 (16)	C22—C23—C24	120.8 (2)
C12—C11—Br1	117.69 (17)	C22—C23—H23	119.6
C11—C12—C13	124.5 (2)	C24—C23—H23	119.6
C11—C12—C17	117.4 (2)	C11—C24—C23	124.9 (2)
C13—C12—C17	118.0 (2)	C11—C24—C19	117.23 (19)
C14—C13—C12	120.8 (2)	C23—C24—C19	117.9 (2)
C14—C13—H13	119.6

C6—C1—C2—C3	1.8 (4)	C17—C12—C13—C14	−0.2 (4)
N1—C1—C2—C3	−179.2 (2)	C12—C13—C14—C15	−0.6 (4)
C1—C2—C3—C4	−0.9 (3)	C13—C14—C15—C16	0.6 (4)
C1—C2—C3—N2	179.4 (2)	C14—C15—C16—C17	0.4 (4)
C2—C3—C4—C5	−0.3 (4)	C15—C16—C17—C18	177.7 (2)
N2—C3—C4—C5	179.4 (2)	C15—C16—C17—C12	−1.2 (4)
C3—C4—C5—C6	0.8 (4)	C11—C12—C17—C18	1.3 (3)
C3—C4—C5—N3	−178.7 (2)	C13—C12—C17—C18	−177.8 (2)
C2—C1—C6—C5	−1.3 (4)	C11—C12—C17—C16	−179.7 (2)
N1—C1—C6—C5	179.6 (2)	C13—C12—C17—C16	1.2 (3)
C4—C5—C6—C1	0.0 (4)	C16—C17—C18—C19	−179.8 (2)
N3—C5—C6—C1	179.5 (2)	C12—C17—C18—C19	−0.8 (3)
C6—C1—N1—O2	−178.3 (2)	C17—C18—C19—C20	179.7 (2)
C2—C1—N1—O2	2.6 (3)	C17—C18—C19—C24	−0.4 (3)
C6—C1—N1—O1	0.8 (3)	C18—C19—C20—C21	178.8 (2)
C2—C1—N1—O1	−178.3 (2)	C24—C19—C20—C21	−1.0 (3)
C2—C3—N2—O4	−179.7 (2)	C19—C20—C21—C22	−0.1 (4)
C4—C3—N2—O4	0.6 (3)	C20—C21—C22—C23	1.1 (4)
C2—C3—N2—O3	0.8 (3)	C21—C22—C23—C24	−0.8 (4)
C4—C3—N2—O3	−179.0 (2)	C12—C11—C24—C23	179.0 (2)
C4—C5—N3—O5	−9.2 (4)	Br1—C11—C24—C23	−1.9 (3)
C6—C5—N3—O5	171.2 (3)	C12—C11—C24—C19	−0.7 (3)
C4—C5—N3—O6	169.6 (3)	Br1—C11—C24—C19	178.46 (16)
C6—C5—N3—O6	−9.9 (4)	C22—C23—C24—C11	179.9 (2)
C24—C11—C12—C13	178.5 (2)	C22—C23—C24—C19	−0.5 (3)
Br1—C11—C12—C13	−0.6 (3)	C18—C19—C24—C11	1.2 (3)
C24—C11—C12—C17	−0.6 (3)	C20—C19—C24—C11	−179.0 (2)
Br1—C11—C12—C17	−179.70 (16)	C18—C19—C24—C23	−178.5 (2)
C11—C12—C13—C14	−179.3 (2)	C20—C19—C24—C23	1.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O6ⁱ	0.95	2.5	3.287 (3)	140
C6—H6···O5ⁱⁱ	0.95	2.68	3.593 (3)	162
C14—H14···O4ⁱⁱⁱ	0.95	2.57	3.255 (3)	129
C21—H21···O1^iv	0.95	2.65	3.364 (3)	132

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

1,3,5-Trinitrobenzene–2-{(E)-[4-(dimethylamino)phenyl]diazenyl}benzoic acid (1/1) (III) top

Crystal data top

C₁₅H₁₅N₃O₂·C₆H₃N₃O₆	Z = 2
M_r = 482.41	F(000) = 500
Triclinic, P1	D_x = 1.518 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.550 (3) Å	Cell parameters from 9824 reflections
b = 10.437 (3) Å	θ = 3.1–28.2°
c = 13.072 (5) Å	µ = 0.12 mm⁻¹
α = 110.689 (10)°	T = 173 K
β = 103.510 (12)°	Cuboid, red
γ = 90.730 (12)°	0.29 × 0.13 × 0.12 mm
V = 1055.2 (7) Å³

Data collection top

Bruker D8 Venture Photon CCD area detector diffractometer	3262 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.072
ω scans	θ_max = 28.0°, θ_min = 3.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.9, T_max = 0.95	k = −13→13
39527 measured reflections	l = −17→17
5072 independent reflections

Refinement top

Refinement on F²	0 constraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.078	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.249	w = 1/[σ²(F_o²) + (0.1346P)² + 0.8758P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
5072 reflections	Δρ_max = 0.49 e Å⁻³
322 parameters	Δρ_min = −0.43 e Å⁻³
0 restraints

Special details top

Experimental. (SADABS; Sheldrick, 1996)

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

	x	y	z	U_iso*/U_eq
C1	0.3627 (3)	0.4196 (3)	0.8376 (2)	0.0274 (6)
C2	0.4468 (3)	0.3469 (3)	0.7610 (2)	0.0265 (6)
H2	0.49673	0.267951	0.76649	0.032*
C3	0.4549 (3)	0.3944 (3)	0.6758 (2)	0.0266 (6)
C4	0.3817 (3)	0.5079 (3)	0.6651 (2)	0.0279 (6)
H4	0.386476	0.537651	0.605026	0.033*
C5	0.3010 (4)	0.5763 (3)	0.7456 (3)	0.0287 (6)
C6	0.2887 (3)	0.5341 (3)	0.8327 (2)	0.0284 (6)
H6	0.231723	0.582036	0.88668	0.034*
N1	0.3560 (3)	0.3737 (3)	0.9312 (2)	0.0324 (6)
N2	0.5442 (3)	0.3204 (3)	0.5938 (2)	0.0305 (6)
N3	0.2291 (3)	0.7015 (3)	0.7399 (2)	0.0367 (6)
O1	0.2796 (3)	0.4374 (3)	0.9979 (2)	0.0475 (6)
O2	0.4303 (3)	0.2766 (3)	0.93921 (19)	0.0437 (6)
O3	0.6018 (3)	0.2169 (2)	0.6015 (2)	0.0405 (6)
O4	0.5548 (3)	0.3668 (3)	0.5212 (2)	0.0435 (6)
O5	0.2266 (3)	0.7301 (3)	0.6567 (2)	0.0485 (7)
O6	0.1772 (3)	0.7707 (3)	0.8201 (2)	0.0507 (7)
C11	0.1578 (3)	0.1335 (3)	0.5551 (2)	0.0255 (6)
C12	0.1935 (4)	0.0433 (3)	0.6139 (2)	0.0272 (6)
H12A	0.258146	−0.028852	0.588579	0.033*
C13	0.1372 (3)	0.0571 (3)	0.7067 (2)	0.0278 (6)
H13	0.163717	−0.004867	0.745181	0.033*
C14	0.0402 (3)	0.1627 (3)	0.7454 (2)	0.0262 (6)
C15	−0.0005 (3)	0.2516 (3)	0.6840 (3)	0.0293 (6)
H15	−0.068293	0.32188	0.707451	0.035*
C16	0.0572 (3)	0.2365 (3)	0.5914 (3)	0.0283 (6)
H16	0.028785	0.296526	0.551294	0.034*
C17	0.0277 (4)	0.0891 (4)	0.9028 (3)	0.0388 (8)
H17A	−0.012745	−0.006156	0.852959	0.058*
H17B	−0.022233	0.116076	0.966614	0.058*
H17C	0.145383	0.096273	0.93118	0.058*
C18	−0.1074 (5)	0.2903 (4)	0.8855 (3)	0.0444 (9)
H18A	−0.116874	0.351673	0.842831	0.067*
H18B	−0.053611	0.342523	0.965088	0.067*
H18C	−0.215479	0.251383	0.87965	0.067*
C19	0.2781 (3)	0.1679 (3)	0.3235 (2)	0.0265 (6)
C20	0.3656 (4)	0.0550 (3)	0.2908 (3)	0.0336 (7)
H20	0.380119	−0.005691	0.331185	0.04*
C21	0.4310 (4)	0.0317 (3)	0.1995 (3)	0.0378 (7)
H21	0.490257	−0.045347	0.177299	0.045*
C22	0.4111 (4)	0.1198 (3)	0.1398 (3)	0.0347 (7)
H22	0.455378	0.10206	0.076507	0.042*
C23	0.3273 (4)	0.2324 (3)	0.1724 (2)	0.0315 (7)
H23	0.314185	0.292407	0.131361	0.038*
C24	0.2613 (3)	0.2597 (3)	0.2650 (2)	0.0259 (6)
C25	0.1757 (4)	0.3865 (3)	0.2948 (3)	0.0338 (7)
N11	0.2263 (3)	0.1105 (2)	0.4652 (2)	0.0280 (6)
N12	0.2057 (3)	0.1977 (3)	0.4154 (2)	0.0282 (6)
N13	−0.0133 (3)	0.1802 (3)	0.8396 (2)	0.0343 (6)
O11	0.1681 (4)	0.4628 (3)	0.2426 (2)	0.0520 (7)
O12	0.1077 (3)	0.4150 (2)	0.3810 (2)	0.0395 (6)
H12	0.130 (6)	0.347 (6)	0.413 (5)	0.096 (18)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0319 (15)	0.0312 (16)	0.0233 (14)	−0.0012 (12)	0.0082 (12)	0.0144 (12)
C2	0.0295 (15)	0.0266 (15)	0.0271 (14)	0.0022 (11)	0.0080 (12)	0.0138 (11)
C3	0.0283 (15)	0.0286 (15)	0.0275 (14)	0.0014 (11)	0.0117 (12)	0.0130 (12)
C4	0.0310 (15)	0.0302 (16)	0.0273 (14)	0.0010 (12)	0.0080 (12)	0.0162 (12)
C5	0.0340 (16)	0.0247 (15)	0.0322 (15)	0.0045 (12)	0.0108 (12)	0.0147 (12)
C6	0.0308 (15)	0.0286 (16)	0.0284 (15)	0.0018 (12)	0.0111 (12)	0.0115 (12)
N1	0.0394 (15)	0.0364 (15)	0.0263 (13)	0.0010 (11)	0.0120 (11)	0.0150 (11)
N2	0.0340 (14)	0.0340 (14)	0.0290 (13)	0.0028 (11)	0.0128 (11)	0.0151 (11)
N3	0.0400 (15)	0.0311 (15)	0.0463 (16)	0.0088 (11)	0.0155 (13)	0.0197 (12)
O1	0.0657 (17)	0.0558 (16)	0.0391 (13)	0.0174 (12)	0.0322 (12)	0.0264 (11)
O2	0.0643 (16)	0.0442 (14)	0.0379 (13)	0.0172 (12)	0.0205 (12)	0.0283 (11)
O3	0.0502 (14)	0.0396 (13)	0.0461 (14)	0.0167 (11)	0.0266 (11)	0.0232 (11)
O4	0.0583 (16)	0.0514 (15)	0.0398 (13)	0.0125 (11)	0.0292 (12)	0.0285 (11)
O5	0.0607 (16)	0.0482 (15)	0.0630 (17)	0.0212 (12)	0.0295 (13)	0.0424 (13)
O6	0.0681 (18)	0.0384 (14)	0.0545 (16)	0.0222 (12)	0.0277 (13)	0.0194 (12)
C11	0.0235 (14)	0.0251 (14)	0.0304 (15)	0.0009 (11)	0.0062 (11)	0.0138 (11)
C12	0.0304 (15)	0.0251 (15)	0.0286 (15)	0.0056 (11)	0.0074 (12)	0.0129 (11)
C13	0.0329 (16)	0.0257 (15)	0.0289 (15)	0.0065 (12)	0.0069 (12)	0.0154 (12)
C14	0.0245 (14)	0.0278 (15)	0.0284 (14)	−0.0001 (11)	0.0056 (11)	0.0134 (12)
C15	0.0269 (15)	0.0301 (16)	0.0361 (16)	0.0075 (12)	0.0095 (12)	0.0173 (13)
C16	0.0280 (15)	0.0289 (15)	0.0332 (15)	0.0029 (11)	0.0062 (12)	0.0185 (12)
C17	0.049 (2)	0.0442 (19)	0.0345 (17)	0.0110 (15)	0.0156 (15)	0.0247 (15)
C18	0.054 (2)	0.047 (2)	0.048 (2)	0.0202 (16)	0.0299 (17)	0.0257 (16)
C19	0.0272 (15)	0.0297 (15)	0.0255 (14)	0.0022 (11)	0.0074 (11)	0.0130 (11)
C20	0.0400 (18)	0.0306 (16)	0.0373 (17)	0.0089 (13)	0.0128 (14)	0.0188 (13)
C21	0.0437 (19)	0.0353 (18)	0.0395 (18)	0.0131 (14)	0.0151 (15)	0.0163 (14)
C22	0.0404 (18)	0.0392 (18)	0.0294 (15)	0.0066 (14)	0.0161 (13)	0.0135 (13)
C23	0.0387 (17)	0.0324 (17)	0.0285 (15)	0.0046 (13)	0.0106 (13)	0.0159 (12)
C24	0.0310 (15)	0.0255 (15)	0.0236 (14)	0.0031 (11)	0.0086 (11)	0.0110 (11)
C25	0.0413 (18)	0.0328 (17)	0.0356 (16)	0.0088 (13)	0.0156 (14)	0.0186 (13)
N11	0.0310 (13)	0.0289 (13)	0.0284 (12)	0.0023 (10)	0.0077 (10)	0.0155 (10)
N12	0.0303 (13)	0.0280 (13)	0.0320 (13)	0.0039 (10)	0.0104 (10)	0.0162 (10)
N13	0.0427 (15)	0.0367 (15)	0.0351 (14)	0.0125 (12)	0.0185 (12)	0.0214 (12)
O11	0.0814 (19)	0.0462 (15)	0.0579 (16)	0.0309 (13)	0.0425 (14)	0.0375 (13)
O12	0.0535 (15)	0.0356 (13)	0.0446 (14)	0.0169 (10)	0.0292 (11)	0.0218 (11)

Geometric parameters (Å, º) top

C1—C6	1.374 (4)	C15—C16	1.371 (4)
C1—C2	1.382 (4)	C15—H15	0.95
C1—N1	1.476 (4)	C16—H16	0.95
C2—C3	1.384 (4)	C17—N13	1.461 (4)
C2—H2	0.95	C17—H17A	0.98
C3—C4	1.382 (4)	C17—H17B	0.98
C3—N2	1.463 (4)	C17—H17C	0.98
C4—C5	1.383 (4)	C18—N13	1.446 (4)
C4—H4	0.95	C18—H18A	0.98
C5—C6	1.383 (4)	C18—H18B	0.98
C5—N3	1.469 (4)	C18—H18C	0.98
C6—H6	0.95	C19—C20	1.396 (4)
N1—O1	1.223 (4)	C19—C24	1.412 (4)
N1—O2	1.225 (4)	C19—N12	1.418 (4)
N2—O3	1.219 (3)	C20—C21	1.380 (5)
N2—O4	1.227 (3)	C20—H20	0.95
N3—O5	1.221 (4)	C21—C22	1.390 (5)
N3—O6	1.228 (4)	C21—H21	0.95
C11—N11	1.381 (4)	C22—C23	1.374 (4)
C11—C16	1.406 (4)	C22—H22	0.95
C11—C12	1.406 (4)	C23—C24	1.395 (4)
C12—C13	1.370 (4)	C23—H23	0.95
C12—H12A	0.95	C24—C25	1.494 (4)
C13—C14	1.408 (4)	C25—O11	1.212 (4)
C13—H13	0.95	C25—O12	1.331 (4)
C14—N13	1.366 (4)	N11—N12	1.285 (3)
C14—C15	1.425 (4)	O12—H12	0.95 (6)

C6—C1—C2	123.5 (3)	C15—C16—C11	120.9 (3)
C6—C1—N1	118.4 (3)	C15—C16—H16	119.6
C2—C1—N1	118.1 (3)	C11—C16—H16	119.6
C1—C2—C3	116.9 (3)	N13—C17—H17A	109.5
C1—C2—H2	121.5	N13—C17—H17B	109.5
C3—C2—H2	121.5	H17A—C17—H17B	109.5
C4—C3—C2	122.6 (3)	N13—C17—H17C	109.5
C4—C3—N2	119.1 (2)	H17A—C17—H17C	109.5
C2—C3—N2	118.3 (3)	H17B—C17—H17C	109.5
C3—C4—C5	117.2 (3)	N13—C18—H18A	109.5
C3—C4—H4	121.4	N13—C18—H18B	109.5
C5—C4—H4	121.4	H18A—C18—H18B	109.5
C6—C5—C4	122.9 (3)	N13—C18—H18C	109.5
C6—C5—N3	118.6 (3)	H18A—C18—H18C	109.5
C4—C5—N3	118.5 (3)	H18B—C18—H18C	109.5
C1—C6—C5	116.9 (3)	C20—C19—C24	119.7 (3)
C1—C6—H6	121.6	C20—C19—N12	123.1 (3)
C5—C6—H6	121.6	C24—C19—N12	117.3 (2)
O1—N1—O2	124.0 (3)	C21—C20—C19	119.8 (3)
O1—N1—C1	117.8 (3)	C21—C20—H20	120.1
O2—N1—C1	118.2 (3)	C19—C20—H20	120.1
O3—N2—O4	124.5 (3)	C20—C21—C22	120.8 (3)
O3—N2—C3	118.1 (2)	C20—C21—H21	119.6
O4—N2—C3	117.3 (3)	C22—C21—H21	119.6
O5—N3—O6	124.7 (3)	C23—C22—C21	120.0 (3)
O5—N3—C5	117.9 (3)	C23—C22—H22	120
O6—N3—C5	117.3 (3)	C21—C22—H22	120
N11—C11—C16	126.2 (3)	C22—C23—C24	120.7 (3)
N11—C11—C12	115.5 (3)	C22—C23—H23	119.7
C16—C11—C12	118.3 (3)	C24—C23—H23	119.7
C13—C12—C11	121.6 (3)	C23—C24—C19	119.1 (3)
C13—C12—H12A	119.2	C23—C24—C25	116.4 (3)
C11—C12—H12A	119.2	C19—C24—C25	124.5 (3)
C12—C13—C14	120.3 (3)	O11—C25—O12	120.1 (3)
C12—C13—H13	119.9	O11—C25—C24	121.4 (3)
C14—C13—H13	119.9	O12—C25—C24	118.4 (3)
N13—C14—C13	121.1 (3)	N12—N11—C11	116.7 (2)
N13—C14—C15	120.6 (3)	N11—N12—C19	114.0 (2)
C13—C14—C15	118.3 (3)	C14—N13—C18	123.2 (3)
C16—C15—C14	120.6 (3)	C14—N13—C17	120.9 (3)
C16—C15—H15	119.7	C18—N13—C17	115.9 (3)
C14—C15—H15	119.7	C25—O12—H12	108 (3)

C6—C1—C2—C3	0.0 (4)	N13—C14—C15—C16	178.1 (3)
N1—C1—C2—C3	−178.3 (3)	C13—C14—C15—C16	−1.7 (4)
C1—C2—C3—C4	−0.8 (4)	C14—C15—C16—C11	−0.1 (4)
C1—C2—C3—N2	179.5 (2)	N11—C11—C16—C15	−178.3 (3)
C2—C3—C4—C5	1.5 (4)	C12—C11—C16—C15	2.1 (4)
N2—C3—C4—C5	−178.9 (3)	C24—C19—C20—C21	−1.8 (5)
C3—C4—C5—C6	−1.4 (4)	N12—C19—C20—C21	179.2 (3)
C3—C4—C5—N3	176.9 (3)	C19—C20—C21—C22	0.1 (5)
C2—C1—C6—C5	0.0 (4)	C20—C21—C22—C23	0.8 (5)
N1—C1—C6—C5	178.4 (3)	C21—C22—C23—C24	−0.1 (5)
C4—C5—C6—C1	0.7 (4)	C22—C23—C24—C19	−1.6 (4)
N3—C5—C6—C1	−177.6 (3)	C22—C23—C24—C25	178.7 (3)
C6—C1—N1—O1	2.5 (4)	C20—C19—C24—C23	2.5 (4)
C2—C1—N1—O1	−179.1 (3)	N12—C19—C24—C23	−178.5 (3)
C6—C1—N1—O2	−175.7 (3)	C20—C19—C24—C25	−177.7 (3)
C2—C1—N1—O2	2.7 (4)	N12—C19—C24—C25	1.3 (4)
C4—C3—N2—O3	−176.7 (3)	C23—C24—C25—O11	−1.7 (5)
C2—C3—N2—O3	2.9 (4)	C19—C24—C25—O11	178.5 (3)
C4—C3—N2—O4	2.8 (4)	C23—C24—C25—O12	178.5 (3)
C2—C3—N2—O4	−177.6 (3)	C19—C24—C25—O12	−1.2 (5)
C6—C5—N3—O5	−172.8 (3)	C16—C11—N11—N12	5.5 (4)
C4—C5—N3—O5	8.8 (4)	C12—C11—N11—N12	−174.9 (2)
C6—C5—N3—O6	7.8 (4)	C11—N11—N12—C19	−179.7 (2)
C4—C5—N3—O6	−170.5 (3)	C20—C19—N12—N11	−0.7 (4)
N11—C11—C12—C13	178.1 (3)	C24—C19—N12—N11	−179.7 (2)
C16—C11—C12—C13	−2.3 (4)	C13—C14—N13—C18	177.4 (3)
C11—C12—C13—C14	0.4 (4)	C15—C14—N13—C18	−2.4 (5)
C12—C13—C14—N13	−178.2 (3)	C13—C14—N13—C17	−0.4 (4)
C12—C13—C14—C15	1.6 (4)	C15—C14—N13—C17	179.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O4ⁱ	0.95	2.35	3.285 (4)	169
C15—H15···O11ⁱⁱ	0.95	2.34	3.254 (4)	161
C18—H18A···O11ⁱⁱ	0.98	2.55	3.519 (4)	170
C20—H20···O3ⁱⁱⁱ	0.95	2.64	3.574 (4)	167
O12—H12···N12	0.95 (6)	1.70 (6)	2.577 (3)	153 (5)
C21—H21···O2ⁱⁱⁱ	0.95	2.56	3.469 (4)	161

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

1,3,5-Trinitrobenzene–1-naphthoic acid–2-amino-5-nitropyridine (1/1/1) (IV) top

Crystal data top

C₆H₃N₃O₆·C₁₁H₈O₂·C₅H₅N₃O₂	Z = 2
M_r = 524.41	F(000) = 540
Triclinic, P1	D_x = 1.571 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5365 (15) Å	Cell parameters from 8623 reflections
b = 7.9003 (16) Å	θ = 3.1–28.3°
c = 19.153 (4) Å	µ = 0.13 mm⁻¹
α = 97.580 (7)°	T = 173 K
β = 94.667 (6)°	Plate, brown
γ = 99.547 (7)°	0.63 × 0.33 × 0.06 mm
V = 1108.5 (4) Å³

Data collection top

Bruker D8 Venture Photon CCD area detector diffractometer	3368 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ω scans	θ_max = 25.5°, θ_min = 3.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.9, T_max = 0.95	k = −9→8
12982 measured reflections	l = −23→23
3988 independent reflections

Refinement top

Refinement on F²	0 constraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.072	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.168	w = 1/[σ²(F_o²) + 2.9593P] where P = (F_o² + 2F_c²)/3
S = 1.22	(Δ/σ)_max < 0.001
3988 reflections	Δρ_max = 0.32 e Å⁻³
355 parameters	Δρ_min = −0.36 e Å⁻³
0 restraints

Special details top

Experimental. (SADABS; Sheldrick, 1996)

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

	x	y	z	U_iso*/U_eq
C1	0.3489 (5)	0.8531 (5)	0.28180 (19)	0.0286 (8)
C2	0.5027 (5)	0.7901 (5)	0.2644 (2)	0.0305 (8)
H2	0.592398	0.774878	0.299662	0.037*
C3	0.5190 (5)	0.7506 (5)	0.1933 (2)	0.0321 (9)
C4	0.3924 (5)	0.7760 (5)	0.1413 (2)	0.0337 (9)
H4	0.406294	0.747525	0.092526	0.04*
C5	0.2448 (5)	0.8441 (5)	0.1624 (2)	0.0309 (8)
C6	0.2177 (5)	0.8818 (5)	0.23294 (19)	0.0287 (8)
H6	0.113733	0.925419	0.246843	0.034*
N1	0.3220 (5)	0.8876 (4)	0.35735 (17)	0.0340 (8)
N2	0.6777 (5)	0.6813 (5)	0.1725 (2)	0.0445 (9)
N3	0.1080 (5)	0.8742 (5)	0.10842 (18)	0.0416 (9)
O1	0.1697 (4)	0.8928 (4)	0.37245 (15)	0.0441 (7)
O2	0.4547 (4)	0.9063 (5)	0.40103 (15)	0.0521 (9)
O3	0.7923 (4)	0.6648 (5)	0.2201 (2)	0.0562 (9)
O4	0.6891 (5)	0.6423 (5)	0.10927 (19)	0.0617 (10)
O5	0.1245 (5)	0.8221 (6)	0.04677 (17)	0.0680 (11)
O6	−0.0122 (4)	0.9495 (5)	0.12813 (17)	0.0520 (8)
C11	0.2801 (5)	0.3592 (5)	0.23195 (19)	0.0283 (8)
C12	0.1324 (5)	0.4164 (5)	0.2022 (2)	0.0339 (9)
H12	0.0557	0.466551	0.232661	0.041*
C13	0.0906 (6)	0.4036 (6)	0.1289 (2)	0.0413 (10)
H13	−0.013342	0.442495	0.109979	0.05*
C14	0.2039 (6)	0.3333 (6)	0.0846 (2)	0.0423 (11)
H14	0.176484	0.322585	0.034787	0.051*
C15	0.3602 (5)	0.2768 (5)	0.11240 (19)	0.0333 (9)
C16	0.4790 (6)	0.2077 (6)	0.0674 (2)	0.0427 (11)
H16	0.451417	0.196379	0.017572	0.051*
C17	0.6309 (6)	0.1573 (6)	0.0937 (2)	0.0465 (11)
H17	0.709603	0.112982	0.06254	0.056*
C18	0.6715 (5)	0.1709 (5)	0.1671 (2)	0.0370 (10)
H18	0.778609	0.136036	0.185356	0.044*
C19	0.5604 (5)	0.2332 (5)	0.2127 (2)	0.0309 (8)
H19	0.590396	0.240016	0.262266	0.037*
C20	0.3986 (5)	0.2887 (5)	0.18715 (19)	0.0296 (8)
C21	0.3071 (5)	0.3680 (5)	0.31063 (19)	0.0293 (8)
O7	0.2603 (4)	0.5052 (4)	0.34527 (15)	0.0370 (7)
O8	0.3642 (4)	0.2557 (4)	0.33988 (14)	0.0385 (7)
H5A	0.309 (7)	0.226 (7)	0.440 (3)	0.058 (15)*
H5B	0.256 (5)	0.144 (6)	0.506 (2)	0.030 (11)*
H7	0.270 (7)	0.503 (7)	0.395 (3)	0.063 (15)*
C22	0.2465 (5)	0.3802 (5)	0.51944 (18)	0.0265 (8)
C23	0.1956 (5)	0.3906 (5)	0.58930 (19)	0.0296 (8)
H23	0.183191	0.291092	0.612665	0.036*
C24	0.1651 (5)	0.5429 (5)	0.62225 (19)	0.0309 (9)
H24	0.132639	0.553261	0.669335	0.037*
C25	0.1822 (5)	0.6859 (5)	0.58541 (19)	0.0272 (8)
C26	0.2293 (5)	0.6680 (5)	0.51770 (19)	0.0295 (8)
H26	0.240027	0.766188	0.493543	0.035*
N4	0.2607 (4)	0.5197 (4)	0.48431 (15)	0.0290 (7)
N5	0.2777 (5)	0.2340 (4)	0.48463 (19)	0.0353 (8)
N6	0.1470 (4)	0.8518 (4)	0.61748 (17)	0.0325 (7)
O9	0.1578 (4)	0.9701 (4)	0.58321 (17)	0.0439 (7)
O10	0.1098 (5)	0.8655 (4)	0.67946 (15)	0.0508 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0303 (19)	0.025 (2)	0.0300 (19)	0.0012 (15)	0.0051 (15)	0.0064 (15)
C2	0.0284 (19)	0.026 (2)	0.038 (2)	0.0046 (16)	0.0043 (16)	0.0101 (16)
C3	0.0267 (19)	0.025 (2)	0.045 (2)	0.0021 (16)	0.0119 (17)	0.0048 (17)
C4	0.034 (2)	0.031 (2)	0.034 (2)	−0.0036 (17)	0.0090 (16)	0.0040 (17)
C5	0.0273 (19)	0.030 (2)	0.033 (2)	−0.0025 (16)	0.0025 (15)	0.0057 (16)
C6	0.0250 (18)	0.0252 (19)	0.036 (2)	0.0028 (15)	0.0065 (15)	0.0047 (16)
N1	0.042 (2)	0.0284 (18)	0.0328 (18)	0.0076 (15)	0.0059 (15)	0.0074 (14)
N2	0.035 (2)	0.037 (2)	0.064 (3)	0.0037 (16)	0.0163 (18)	0.0109 (19)
N3	0.037 (2)	0.050 (2)	0.034 (2)	−0.0059 (17)	0.0021 (15)	0.0095 (17)
O1	0.0461 (18)	0.052 (2)	0.0390 (16)	0.0127 (15)	0.0175 (14)	0.0090 (14)
O2	0.0512 (19)	0.069 (2)	0.0340 (16)	0.0103 (17)	−0.0051 (14)	0.0065 (15)
O3	0.0378 (18)	0.056 (2)	0.083 (3)	0.0206 (15)	0.0153 (17)	0.0201 (19)
O4	0.052 (2)	0.068 (3)	0.064 (2)	0.0079 (18)	0.0286 (17)	−0.0023 (19)
O5	0.058 (2)	0.107 (3)	0.0313 (18)	0.004 (2)	−0.0025 (15)	0.0035 (18)
O6	0.0405 (18)	0.066 (2)	0.0508 (19)	0.0108 (16)	0.0000 (15)	0.0138 (17)
C11	0.0286 (19)	0.024 (2)	0.0307 (19)	0.0004 (15)	0.0074 (15)	0.0017 (15)
C12	0.030 (2)	0.033 (2)	0.039 (2)	0.0021 (17)	0.0073 (17)	0.0092 (17)
C13	0.033 (2)	0.047 (3)	0.040 (2)	−0.0048 (19)	−0.0023 (18)	0.0105 (19)
C14	0.044 (2)	0.046 (3)	0.030 (2)	−0.006 (2)	−0.0002 (18)	0.0029 (19)
C15	0.035 (2)	0.034 (2)	0.0260 (19)	−0.0062 (17)	0.0064 (16)	−0.0008 (16)
C16	0.055 (3)	0.041 (3)	0.030 (2)	0.002 (2)	0.0142 (19)	−0.0001 (18)
C17	0.049 (3)	0.044 (3)	0.044 (2)	0.000 (2)	0.018 (2)	−0.001 (2)
C18	0.032 (2)	0.035 (2)	0.041 (2)	−0.0008 (17)	0.0113 (17)	−0.0005 (18)
C19	0.0294 (19)	0.026 (2)	0.035 (2)	0.0004 (16)	0.0047 (16)	0.0007 (16)
C20	0.032 (2)	0.025 (2)	0.0282 (19)	−0.0052 (16)	0.0064 (15)	0.0018 (15)
C21	0.0298 (19)	0.027 (2)	0.031 (2)	0.0026 (16)	0.0085 (15)	0.0050 (17)
O7	0.0569 (18)	0.0299 (16)	0.0279 (15)	0.0144 (13)	0.0103 (13)	0.0055 (12)
O8	0.0495 (17)	0.0396 (17)	0.0307 (14)	0.0163 (14)	0.0107 (12)	0.0064 (13)
C22	0.0257 (18)	0.026 (2)	0.0279 (18)	0.0047 (15)	0.0000 (14)	0.0045 (15)
C23	0.0316 (19)	0.032 (2)	0.0265 (19)	0.0071 (16)	0.0016 (15)	0.0087 (16)
C24	0.033 (2)	0.034 (2)	0.0249 (18)	0.0044 (17)	0.0033 (15)	0.0053 (16)
C25	0.0253 (18)	0.028 (2)	0.0278 (18)	0.0037 (15)	0.0020 (14)	0.0022 (15)
C26	0.033 (2)	0.023 (2)	0.032 (2)	0.0046 (16)	0.0036 (16)	0.0052 (16)
N4	0.0364 (17)	0.0246 (17)	0.0265 (16)	0.0041 (13)	0.0071 (13)	0.0043 (13)
N5	0.057 (2)	0.0199 (18)	0.0309 (18)	0.0082 (16)	0.0117 (16)	0.0045 (15)
N6	0.0298 (17)	0.0297 (19)	0.0373 (19)	0.0056 (14)	0.0041 (14)	0.0019 (15)
O9	0.0505 (18)	0.0277 (16)	0.0605 (19)	0.0122 (13)	0.0210 (15)	0.0159 (14)
O10	0.075 (2)	0.051 (2)	0.0318 (16)	0.0285 (17)	0.0119 (15)	0.0012 (14)

Geometric parameters (Å, º) top

C1—C6	1.373 (5)	C15—C20	1.425 (5)
C1—C2	1.382 (5)	C16—C17	1.354 (7)
C1—N1	1.474 (5)	C16—H16	0.95
C2—C3	1.376 (5)	C17—C18	1.400 (6)
C2—H2	0.95	C17—H17	0.95
C3—C4	1.380 (6)	C18—C19	1.360 (5)
C3—N2	1.458 (5)	C18—H18	0.95
C4—C5	1.380 (6)	C19—C20	1.434 (6)
C4—H4	0.95	C19—H19	0.95
C5—C6	1.383 (5)	C21—O8	1.227 (5)
C5—N3	1.470 (5)	C21—O7	1.309 (5)
C6—H6	0.95	O7—H7	0.95 (5)
N1—O1	1.212 (4)	C22—N5	1.321 (5)
N1—O2	1.227 (4)	C22—N4	1.359 (5)
N2—O4	1.222 (5)	C22—C23	1.418 (5)
N2—O3	1.240 (5)	C23—C24	1.347 (6)
N3—O5	1.221 (5)	C23—H23	0.95
N3—O6	1.222 (5)	C24—C25	1.403 (5)
C11—C12	1.378 (5)	C24—H24	0.95
C11—C20	1.417 (5)	C25—C26	1.368 (5)
C11—C21	1.495 (5)	C25—N6	1.447 (5)
C12—C13	1.400 (6)	C26—N4	1.325 (5)
C12—H12	0.95	C26—H26	0.95
C13—C14	1.380 (6)	N5—H5A	0.90 (5)
C13—H13	0.95	N5—H5B	0.86 (4)
C14—C15	1.416 (6)	N6—O9	1.207 (4)
C14—H14	0.95	N6—O10	1.237 (4)
C15—C16	1.416 (6)

C6—C1—C2	124.0 (3)	C17—C16—C15	121.7 (4)
C6—C1—N1	117.9 (3)	C17—C16—H16	119.2
C2—C1—N1	118.1 (3)	C15—C16—H16	119.2
C3—C2—C1	116.6 (4)	C16—C17—C18	119.7 (4)
C3—C2—H2	121.7	C16—C17—H17	120.2
C1—C2—H2	121.7	C18—C17—H17	120.2
C2—C3—C4	122.5 (4)	C19—C18—C17	121.1 (4)
C2—C3—N2	118.5 (4)	C19—C18—H18	119.4
C4—C3—N2	119.0 (4)	C17—C18—H18	119.4
C5—C4—C3	117.8 (4)	C18—C19—C20	121.0 (4)
C5—C4—H4	121.1	C18—C19—H19	119.5
C3—C4—H4	121.1	C20—C19—H19	119.5
C4—C5—C6	122.5 (4)	C11—C20—C15	118.9 (4)
C4—C5—N3	119.3 (3)	C11—C20—C19	123.7 (3)
C6—C5—N3	118.2 (4)	C15—C20—C19	117.3 (4)
C1—C6—C5	116.5 (4)	O8—C21—O7	123.2 (3)
C1—C6—H6	121.7	O8—C21—C11	123.2 (4)
C5—C6—H6	121.7	O7—C21—C11	113.5 (3)
O1—N1—O2	124.1 (3)	C21—O7—H7	112 (3)
O1—N1—C1	118.0 (3)	N5—C22—N4	116.8 (3)
O2—N1—C1	117.9 (3)	N5—C22—C23	121.9 (4)
O4—N2—O3	124.1 (4)	N4—C22—C23	121.3 (3)
O4—N2—C3	118.1 (4)	C24—C23—C22	119.4 (4)
O3—N2—C3	117.8 (4)	C24—C23—H23	120.3
O5—N3—O6	124.9 (4)	C22—C23—H23	120.3
O5—N3—C5	116.9 (4)	C23—C24—C25	118.4 (3)
O6—N3—C5	118.1 (3)	C23—C24—H24	120.8
C12—C11—C20	119.2 (3)	C25—C24—H24	120.8
C12—C11—C21	118.9 (3)	C26—C25—C24	119.7 (4)
C20—C11—C21	121.9 (3)	C26—C25—N6	119.4 (3)
C11—C12—C13	122.8 (4)	C24—C25—N6	120.9 (3)
C11—C12—H12	118.6	N4—C26—C25	122.9 (4)
C13—C12—H12	118.6	N4—C26—H26	118.5
C14—C13—C12	118.5 (4)	C25—C26—H26	118.5
C14—C13—H13	120.7	C26—N4—C22	118.2 (3)
C12—C13—H13	120.7	C22—N5—H5A	123 (3)
C13—C14—C15	121.1 (4)	C22—N5—H5B	116 (3)
C13—C14—H14	119.5	H5A—N5—H5B	121 (4)
C15—C14—H14	119.5	O9—N6—O10	123.2 (3)
C14—C15—C16	121.4 (4)	O9—N6—C25	118.9 (3)
C14—C15—C20	119.4 (4)	O10—N6—C25	117.9 (3)
C16—C15—C20	119.1 (4)

C6—C1—C2—C3	−1.8 (6)	C15—C16—C17—C18	1.0 (7)
N1—C1—C2—C3	176.7 (3)	C16—C17—C18—C19	0.3 (7)
C1—C2—C3—C4	1.7 (6)	C17—C18—C19—C20	−0.6 (6)
C1—C2—C3—N2	−179.1 (3)	C12—C11—C20—C15	−0.8 (5)
C2—C3—C4—C5	0.2 (6)	C21—C11—C20—C15	177.1 (3)
N2—C3—C4—C5	−179.1 (3)	C12—C11—C20—C19	177.0 (4)
C3—C4—C5—C6	−2.1 (6)	C21—C11—C20—C19	−5.1 (5)
C3—C4—C5—N3	179.5 (3)	C14—C15—C20—C11	−0.8 (5)
C2—C1—C6—C5	0.1 (6)	C16—C15—C20—C11	179.5 (3)
N1—C1—C6—C5	−178.4 (3)	C14—C15—C20—C19	−178.8 (4)
C4—C5—C6—C1	1.9 (5)	C16—C15—C20—C19	1.6 (5)
N3—C5—C6—C1	−179.6 (3)	C18—C19—C20—C11	−178.2 (4)
C6—C1—N1—O1	19.8 (5)	C18—C19—C20—C15	−0.3 (5)
C2—C1—N1—O1	−158.8 (4)	C12—C11—C21—O8	142.1 (4)
C6—C1—N1—O2	−161.4 (4)	C20—C11—C21—O8	−35.8 (5)
C2—C1—N1—O2	20.0 (5)	C12—C11—C21—O7	−36.5 (5)
C2—C3—N2—O4	178.1 (4)	C20—C11—C21—O7	145.6 (3)
C4—C3—N2—O4	−2.6 (5)	N5—C22—C23—C24	−179.8 (4)
C2—C3—N2—O3	−1.5 (5)	N4—C22—C23—C24	−1.7 (5)
C4—C3—N2—O3	177.8 (4)	C22—C23—C24—C25	1.0 (5)
C4—C5—N3—O5	6.4 (5)	C23—C24—C25—C26	−0.1 (5)
C6—C5—N3—O5	−172.1 (4)	C23—C24—C25—N6	178.6 (3)
C4—C5—N3—O6	−173.2 (4)	C24—C25—C26—N4	−0.1 (6)
C6—C5—N3—O6	8.3 (5)	N6—C25—C26—N4	−178.8 (3)
C20—C11—C12—C13	1.8 (6)	C25—C26—N4—C22	−0.5 (5)
C21—C11—C12—C13	−176.1 (4)	N5—C22—N4—C26	179.7 (3)
C11—C12—C13—C14	−1.0 (6)	C23—C22—N4—C26	1.5 (5)
C12—C13—C14—C15	−0.7 (6)	C26—C25—N6—O9	1.0 (5)
C13—C14—C15—C16	−178.7 (4)	C24—C25—N6—O9	−177.7 (3)
C13—C14—C15—C20	1.6 (6)	C26—C25—N6—O10	−178.0 (3)
C14—C15—C16—C17	178.4 (4)	C24—C25—N6—O10	3.4 (5)
C20—C15—C16—C17	−1.9 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5A···O8	0.90 (5)	2.03 (5)	2.919 (5)	168 (5)
N5—H5B···O9ⁱ	0.86 (4)	2.24 (4)	3.069 (5)	161 (4)
O7—H7···N4	0.95 (5)	1.71 (5)	2.650 (4)	171 (5)
C23—H23···O9ⁱ	0.95	2.5	3.272 (5)	139
C26—H26···O1	0.95	2.69	3.530 (5)	147
C26—H26···O2	0.95	2.72	3.477 (5)	138

Symmetry code: (i) x, y−1, z.

Centroid distances (Å) between the trinitrobenzene and the ring centroids (Cg) of the aromatic polycyclics top

Structure	Donor	Acceptor	Cg···Cg	Symmetry operator
(I)	C1–C6	C11–C20	3.3745 (2)	x, y, z
(II)	C1–C6	C11–C24	3.5173 (11)	x, y, z
(III)	C1–C6	C11–C16	3.6587 (14)	1 - x, 1 - y, 1 - z
(III)	C1–C6	C19–C24	4.6432 (18)	x, y, z
(IV)	C1–C6	C11–C20	4.0417 (8)	x, y + 1, z

Proportion (%) of intermolecular contacts between donor and acceptor molecules in the Hirshfeld fingerprint plots top

Structure	C···C	H···H	C···H
(I)	12.0	10.7	1.5
(II)	12.6	6.6	0.9
(III)	4.4	11.0	5.4
(IV)	7.5	8.8	4.6

Funding information

This material is based upon work supported financially by the University of the Witwatersrand Friedel Sellschop Grant and the Molecular Sciences Institute. Tania Hill thanks the University of the Witwatersrand Research Office for a postdoctoral fellowship. The National Research Foundation National Equipment Programme (UID: 78572) is thanked for financing the purchase of the single-crystal diffractometer. Any opinions, findings and conclusions or recommendations expressed in this material are those of the authors and therefore the NRF does not accept any liability in regard thereto.

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Volume 74| Part 2| February 2018| Pages 113-118

https://doi.org/10.1107/S2056989018000245

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